##############################################################################
# #
# This CIF contains the data in a paper accepted for publication in #
# Acta Crystallographica Section E. It conforms to the requirements of #
# Notes for Authors for Acta Crystallographica Section E, and has been #
# peer reviewed under the auspices of the IUCr Commission on Journals. #
# #
# Full details of the Crystallographic Information File format #
# are given in the paper "The Crystallographic Information File (CIF): #
# a New Standard Archive File for Crystallography" by S. R. Hall, F. H. #
# Allen and I. D. Brown [Acta Cryst. (1991), A47, 655-685]. #
# #
# The current version of the core CIF dictionary is obtainable from #
# ftp://ftp.iucr.org/pub/cif_core.dic. #
# #
# Software is freely available for graphical display of the structure(s) #
# in this CIF. For information consult the CIF software page #
# http://www.iucr.org/resources/cif/software. #
# #
# This file may be used for bona fide research purposes within the #
# scientific community so long as proper attribution is given to the journal #
# article from which it was obtained. #
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##############################################################################
data_I
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
(E)-2-[2-(4-Chlorobenzylidene)hydrazin-1-yl]-
4-{[3-(dimethylazaniumyl)propyl]amino}quinazolin-1-ium bis(perchlorate)
;
_chemical_name_common ?
_chemical_formula_moiety 'C20 H25 Cl N6 2+, 2(Cl O4 -)'
_chemical_formula_sum 'C20 H25 Cl3 N6 O8'
_chemical_formula_iupac 'C20 H25 Cl N6 2+, 2Cl O4 -'
_chemical_formula_weight 583.81
_chemical_melting_point ?
_symmetry_cell_setting triclinic
_symmetry_space_group_name_H-M 'P -1'
_symmetry_space_group_name_Hall '-P 1'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
_cell_length_a 10.4533(18)
_cell_length_b 10.5018(18)
_cell_length_c 12.626(2)
_cell_angle_alpha 104.745(9)
_cell_angle_beta 91.146(10)
_cell_angle_gamma 96.210(10)
_cell_volume 1330.9(4)
_cell_formula_units_Z 2
_cell_measurement_reflns_used 4829
_cell_measurement_theta_min 2.513
_cell_measurement_theta_max 30.103
_cell_measurement_temperature 293(2)
_exptl_crystal_description block
_exptl_crystal_colour colorless
_exptl_crystal_size_max 0.25
_exptl_crystal_size_mid 0.23
_exptl_crystal_size_min 0.18
_exptl_crystal_density_diffrn 1.457
_exptl_crystal_density_meas ?
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 604
_exptl_absorpt_coefficient_mu 0.399
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)'
_exptl_absorpt_correction_T_min 0.9068
_exptl_absorpt_correction_T_max 0.9316
_exptl_special_details
;
;
_diffrn_ambient_temperature 293(2)
_diffrn_radiation_type MoK\a
_diffrn_radiation_wavelength 0.71073
_diffrn_radiation_source 'fine-focus sealed tube'
_diffrn_radiation_monochromator graphite
_diffrn_measurement_device_type 'Siemens SMART CCD area-detector'
_diffrn_measurement_method 'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number 12435
_diffrn_reflns_av_R_equivalents 0.0228
_diffrn_reflns_av_sigmaI/netI 0.0268
_diffrn_reflns_theta_min 1.67
_diffrn_reflns_theta_max 25.50
_diffrn_reflns_theta_full 25.50
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.987
_diffrn_reflns_limit_h_min -12
_diffrn_reflns_limit_h_max 12
_diffrn_reflns_limit_k_min -12
_diffrn_reflns_limit_k_max 12
_diffrn_reflns_limit_l_min -14
_diffrn_reflns_limit_l_max 15
_diffrn_standards_number ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time ?
_diffrn_standards_decay_% ?
_refine_special_details
;
Refinement of F^2^ against ALL reflections. The weighted R-factor
wR and goodness of fit S are based on F^2^, conventional
R-factors R are based on F, with F set to zero for
negative F^2^. The threshold expression of F^2^ >
\s(F^2^) is used only for calculating R-factors(gt) etc.
and is not relevant to the choice of reflections for refinement.
R-factors based on F^2^ are statistically about twice as large
as those based on F, and R- factors based on ALL data will be
even larger.
;
_reflns_number_total 4889
_reflns_number_gt 3979
_reflns_threshold_expression I>2sigma(I)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_R_factor_all 0.0833
_refine_ls_R_factor_gt 0.0714
_refine_ls_wR_factor_gt 0.2066
_refine_ls_wR_factor_ref 0.2191
_refine_ls_goodness_of_fit_ref 1.089
_refine_ls_restrained_S_all 1.127
_refine_ls_number_reflns 4889
_refine_ls_number_parameters 371
_refine_ls_number_restraints 62
_refine_ls_hydrogen_treatment constr
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.1339P)^2^+1.0689P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_hydrogens geom
_atom_sites_solution_primary direct
_atom_sites_solution_secondary difmap
_refine_ls_shift/su_max 0.000
_refine_ls_shift/su_mean 0.000
_refine_diff_density_max 0.694
_refine_diff_density_min -0.917
_refine_ls_extinction_method none
_refine_ls_extinction_coef ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
'C' 'C' 0.0033 0.0016
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
'H' 'H' 0.0000 0.0000
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
'N' 'N' 0.0061 0.0033
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
'O' 'O' 0.0106 0.0060
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
'Cl' 'Cl' 0.1484 0.1585
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection 'SMART (Siemens, 1996)'
_computing_cell_refinement 'SAINT (Siemens, 1996)'
_computing_data_reduction 'SAINT (Siemens, 1996)'
_computing_structure_solution 'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics 'SHELXTL (Sheldrick, 2008)'
_computing_publication_material 'SHELXTL (Sheldrick, 2008)'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl Cl1 0.32941(8) 0.74253(8) 0.10002(7) 0.0433(3) Uani d . 1 1 . .
Cl Cl2 0.26374(10) 0.25136(12) 0.61278(8) 0.0638(4) Uani d . 1 1 . .
Cl Cl3 -0.49702(12) 0.78162(13) -0.25924(10) 0.0702(4) Uani d . 1 1 B .
N N2 0.2182(3) 0.4226(3) 0.3840(3) 0.0455(7) Uani d . 1 1 . .
H H2D 0.2213 0.3602 0.4166 0.055 Uiso calc R 1 1 A 1
N N3 0.1121(3) 0.5197(3) 0.2718(2) 0.0391(6) Uani d . 1 1 . .
N N4 -0.0771(3) 0.4117(3) 0.1697(2) 0.0380(6) Uani d . 1 1 . .
H H4C -0.1379 0.4135 0.1234 0.046 Uiso calc R 1 1 B .
N N5 0.0158(3) 0.6172(3) 0.1555(2) 0.0399(6) Uani d . 1 1 . .
H H5C 0.0781 0.6806 0.1710 0.048 Uiso calc R 1 1 B .
N N6 -0.0855(3) 0.6209(3) 0.0851(2) 0.0369(6) Uani d . 1 1 B .
O O1 0.3001(3) 0.6543(3) -0.0088(2) 0.0553(7) Uani d . 1 1 . .
O O2 0.2245(3) 0.8192(3) 0.1395(3) 0.0617(8) Uani d . 1 1 . .
O O3 0.3692(3) 0.6777(3) 0.1811(2) 0.0582(7) Uani d . 1 1 . .
O O4 0.4611(4) 0.8581(4) 0.0865(4) 0.1015(14) Uani d . 1 1 . .
O O5 0.1324(4) 0.2708(10) 0.6082(4) 0.201(4) Uani d . 1 1 . .
O O6 0.2930(6) 0.1273(4) 0.6352(4) 0.123(2) Uani d . 1 1 . .
O O7 0.3248(4) 0.2711(4) 0.5170(3) 0.0731(9) Uani d . 1 1 . .
O O8 0.3333(5) 0.3762(5) 0.7247(4) 0.1072(14) Uani d . 1 1 . .
C C1 0.3790(6) 0.9314(8) 0.3904(6) 0.094(3) Uani d PDU 0.768(10) 1 B 1
H H1B 0.3551 0.9663 0.3306 0.141 Uiso calc PR 0.768(10) 1 B 1
H H1C 0.4612 0.8987 0.3783 0.141 Uiso calc PR 0.768(10) 1 B 1
H H1D 0.3842 1.0001 0.4576 0.141 Uiso calc PR 0.768(10) 1 B 1
C C2 0.1534(15) 0.8623(13) 0.3983(9) 0.054(3) Uani d PU 0.768(10) 1 B 1
H H2A 0.0894 0.7915 0.4033 0.081 Uiso calc PR 0.768(10) 1 B 1
H H2B 0.1373 0.8877 0.3318 0.081 Uiso calc PR 0.768(10) 1 B 1
H H2C 0.1493 0.9370 0.4601 0.081 Uiso calc PR 0.768(10) 1 B 1
N N1 0.2784(4) 0.8189(4) 0.3980(3) 0.0711(11) Uani d PDU 0.768(10) 1 B 1
H H1A 0.2818 0.7500 0.3379 0.085 Uiso calc PR 0.768(10) 1 B 1
C C3 0.3380(7) 0.7866(6) 0.4925(5) 0.071(2) Uani d PDU 0.768(10) 1 B 1
H H3A 0.3252 0.8526 0.5596 0.085 Uiso calc PR 0.768(10) 1 B 1
H H3B 0.4297 0.7839 0.4841 0.085 Uiso calc PR 0.768(10) 1 B 1
C C4 0.2729(9) 0.6522(6) 0.4957(5) 0.079(3) Uani d PDU 0.768(10) 1 B 1
H H4A 0.1807 0.6504 0.4836 0.095 Uiso calc PR 0.768(10) 1 B 1
H H4B 0.2881 0.6397 0.5683 0.095 Uiso calc PR 0.768(10) 1 B 1
C C5 0.3222(4) 0.5303(4) 0.4057(4) 0.0635(12) Uani d PD 0.768(10) 1 B 1
H H5A 0.3423 0.5563 0.3390 0.076 Uiso calc PR 0.768(10) 1 B 1
H H5B 0.3990 0.5033 0.4340 0.076 Uiso calc PR 0.768(10) 1 B 1
C C1' 0.4014(16) 0.885(3) 0.438(2) 0.081(7) Uani d PDU 0.232(10) 1 B 2
H H1'B 0.4612 0.8206 0.4339 0.121 Uiso calc PR 0.232(10) 1 B 2
H H1'C 0.3972 0.9346 0.5124 0.121 Uiso calc PR 0.232(10) 1 B 2
H H1'D 0.4297 0.9437 0.3936 0.121 Uiso calc PR 0.232(10) 1 B 2
C C2' 0.156(4) 0.896(4) 0.397(4) 0.059(11) Uani d PU 0.232(10) 1 B 2
H H2'A 0.1676 0.9518 0.3478 0.089 Uiso calc PR 0.232(10) 1 B 2
H H2'B 0.1452 0.9492 0.4697 0.089 Uiso calc PR 0.232(10) 1 B 2
H H2'C 0.0805 0.8331 0.3734 0.089 Uiso calc PR 0.232(10) 1 B 2
N N1' 0.2784(4) 0.8189(4) 0.3980(3) 0.0711(11) Uani d PDU 0.232(10) 1 B 2
H H1'A 0.2844 0.7628 0.3307 0.085 Uiso calc PR 0.232(10) 1 B 2
C C3' 0.2400(10) 0.7379(10) 0.4811(8) 0.027(4) Uani d PDU 0.232(10) 1 B 2
H H3'A 0.2259 0.7983 0.5508 0.032 Uiso calc PR 0.232(10) 1 B 2
H H3'B 0.1594 0.6825 0.4552 0.032 Uiso calc PR 0.232(10) 1 B 2
C C4' 0.3425(12) 0.6497(11) 0.4986(10) 0.033(4) Uani d PDU 0.232(10) 1 B 2
H H4'A 0.4283 0.6954 0.4992 0.040 Uiso calc PR 0.232(10) 1 B 2
H H4'B 0.3320 0.6261 0.5676 0.040 Uiso calc PR 0.232(10) 1 B 2
C C5' 0.3222(4) 0.5303(4) 0.4057(4) 0.0635(12) Uani d PD 0.232(10) 1 B 2
H H5'A 0.3229 0.5634 0.3407 0.076 Uiso calc PR 0.232(10) 1 B 2
H H5'B 0.4003 0.4881 0.4056 0.076 Uiso calc PR 0.232(10) 1 B 2
C C6 0.1190(3) 0.4168(3) 0.3162(3) 0.0377(7) Uani d . 1 1 B .
C C7 0.0215(3) 0.3013(3) 0.2901(3) 0.0377(7) Uani d . 1 1 . .
C C8 0.0235(4) 0.1903(4) 0.3319(3) 0.0476(8) Uani d . 1 1 B .
H H8 0.0881 0.1891 0.3833 0.057 Uiso calc R 1 1 . .
C C9 -0.0688(4) 0.0830(4) 0.2980(3) 0.0523(9) Uani d . 1 1 . .
H H9 -0.0663 0.0093 0.3258 0.063 Uiso calc R 1 1 B .
C C10 -0.1655(4) 0.0850(4) 0.2224(3) 0.0535(9) Uani d . 1 1 B .
H H10 -0.2279 0.0121 0.1998 0.064 Uiso calc R 1 1 . .
C C11 -0.1714(4) 0.1935(4) 0.1798(3) 0.0491(9) Uani d . 1 1 . .
H H11 -0.2375 0.1940 0.1297 0.059 Uiso calc R 1 1 B .
C C12 -0.0763(3) 0.3026(3) 0.2132(3) 0.0384(7) Uani d . 1 1 B .
C C13 0.0161(3) 0.5139(3) 0.1994(3) 0.0353(7) Uani d . 1 1 B .
C C14 -0.0831(3) 0.7243(3) 0.0498(3) 0.0398(7) Uani d . 1 1 . .
H H14 -0.0154 0.7918 0.0722 0.048 Uiso calc R 1 1 B .
C C15 -0.1847(3) 0.7380(3) -0.0249(3) 0.0376(7) Uani d . 1 1 B .
C C16 -0.2904(3) 0.6397(3) -0.0569(3) 0.0425(8) Uani d . 1 1 . .
H H16 -0.2963 0.5654 -0.0292 0.051 Uiso calc R 1 1 B .
C C17 -0.3850(4) 0.6532(4) -0.1289(3) 0.0478(9) Uani d . 1 1 B .
H H17 -0.4547 0.5880 -0.1506 0.057 Uiso calc R 1 1 . .
C C18 -0.3756(3) 0.7649(4) -0.1690(3) 0.0440(8) Uani d . 1 1 . .
C C19 -0.2739(4) 0.8635(4) -0.1393(3) 0.0464(8) Uani d . 1 1 B .
H H19 -0.2689 0.9374 -0.1676 0.056 Uiso calc R 1 1 . .
C C20 -0.1798(3) 0.8500(3) -0.0664(3) 0.0437(8) Uani d . 1 1 . .
H H20 -0.1113 0.9168 -0.0442 0.052 Uiso calc R 1 1 B .
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
Cl1 0.0423(5) 0.0379(5) 0.0468(5) -0.0048(3) -0.0039(3) 0.0099(4)
Cl2 0.0543(6) 0.0819(8) 0.0474(6) -0.0141(5) -0.0011(4) 0.0116(5)
Cl3 0.0688(7) 0.0759(8) 0.0666(7) 0.0096(6) -0.0302(5) 0.0216(6)
N2 0.0436(16) 0.0429(16) 0.0513(17) 0.0030(12) -0.0128(13) 0.0165(13)
N3 0.0363(14) 0.0390(15) 0.0406(15) 0.0044(11) -0.0049(11) 0.0086(12)
N4 0.0353(14) 0.0420(15) 0.0369(14) 0.0026(11) -0.0058(11) 0.0119(12)
N5 0.0338(14) 0.0432(16) 0.0436(15) 0.0020(11) -0.0071(11) 0.0144(12)
N6 0.0329(13) 0.0410(15) 0.0375(14) 0.0041(11) -0.0051(11) 0.0119(12)
O1 0.0659(17) 0.0486(15) 0.0455(14) -0.0049(13) -0.0153(12) 0.0072(12)
O2 0.0433(15) 0.0480(16) 0.090(2) -0.0004(12) 0.0120(14) 0.0124(15)
O3 0.0685(18) 0.0532(16) 0.0528(16) -0.0003(13) -0.0138(13) 0.0178(13)
O4 0.081(3) 0.082(3) 0.126(3) -0.016(2) 0.024(2) 0.008(2)
O5 0.042(2) 0.408(12) 0.098(4) 0.007(4) -0.017(2) -0.026(5)
O6 0.222(6) 0.058(2) 0.084(3) -0.029(3) 0.009(3) 0.029(2)
O7 0.092(2) 0.086(2) 0.0534(17) 0.0278(19) 0.0155(16) 0.0313(16)
O8 0.091(3) 0.111(3) 0.102(3) 0.006(2) -0.008(2) -0.001(3)
C1 0.047(3) 0.133(7) 0.067(4) 0.006(4) -0.015(3) -0.034(4)
C2 0.064(5) 0.042(8) 0.051(4) 0.011(5) -0.003(3) 0.002(4)
N1 0.096(3) 0.074(2) 0.0416(18) 0.044(2) -0.0082(17) -0.0013(16)
C3 0.078(5) 0.075(4) 0.054(3) 0.008(4) -0.011(3) 0.006(3)
C4 0.095(6) 0.089(5) 0.037(3) -0.045(5) -0.012(3) 0.011(3)
C5 0.064(3) 0.056(2) 0.072(3) -0.012(2) -0.034(2) 0.031(2)
C1' 0.094(11) 0.083(10) 0.079(10) 0.007(8) -0.001(8) 0.048(9)
C2' 0.037(11) 0.009(12) 0.12(2) 0.001(8) 0.015(11) 0.005(10)
N1' 0.096(3) 0.074(2) 0.0416(18) 0.044(2) -0.0082(17) -0.0013(16)
C3' 0.026(7) 0.016(6) 0.029(6) -0.008(5) -0.003(5) -0.009(5)
C4' 0.016(6) 0.052(7) 0.028(6) -0.018(5) -0.016(5) 0.013(5)
C5' 0.064(3) 0.056(2) 0.072(3) -0.012(2) -0.034(2) 0.031(2)
C6 0.0398(17) 0.0392(17) 0.0345(16) 0.0077(13) -0.0010(13) 0.0095(13)
C7 0.0377(17) 0.0405(18) 0.0348(16) 0.0041(13) -0.0003(13) 0.0100(13)
C8 0.050(2) 0.049(2) 0.049(2) 0.0068(16) -0.0018(16) 0.0198(16)
C9 0.055(2) 0.048(2) 0.057(2) 0.0001(17) 0.0010(18) 0.0220(18)
C10 0.054(2) 0.046(2) 0.059(2) -0.0074(17) -0.0009(18) 0.0162(18)
C11 0.0455(19) 0.054(2) 0.047(2) -0.0047(16) -0.0081(15) 0.0169(17)
C12 0.0374(16) 0.0400(18) 0.0375(17) 0.0020(13) 0.0027(13) 0.0102(14)
C13 0.0353(16) 0.0379(17) 0.0333(15) 0.0085(13) 0.0006(12) 0.0088(13)
C14 0.0372(17) 0.0385(18) 0.0428(18) 0.0018(13) -0.0055(13) 0.0102(14)
C15 0.0394(17) 0.0347(17) 0.0379(16) 0.0065(13) -0.0014(13) 0.0073(13)
C16 0.0475(19) 0.0337(17) 0.0449(18) 0.0031(14) -0.0054(15) 0.0091(14)
C17 0.049(2) 0.0392(19) 0.049(2) 0.0010(15) -0.0108(16) 0.0037(15)
C18 0.0437(18) 0.051(2) 0.0357(17) 0.0128(15) -0.0069(14) 0.0059(15)
C19 0.052(2) 0.0432(19) 0.050(2) 0.0102(16) -0.0016(16) 0.0206(16)
C20 0.0400(18) 0.0367(18) 0.056(2) 0.0017(14) -0.0035(15) 0.0155(15)
_geom_special_details
;
All e.s.d.'s (except the e.s.d. in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell e.s.d.'s are taken
into account individually in the estimation of e.s.d.'s in distances, angles
and torsion angles; correlations between e.s.d.'s in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell e.s.d.'s is used for estimating e.s.d.'s involving l.s.
planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 O3 . 1.444(3) ?
Cl1 O2 . 1.452(3) ?
Cl1 O1 . 1.454(3) ?
Cl1 O4 . 1.775(4) ?
Cl2 O5 . 1.412(5) ?
Cl2 O7 . 1.430(3) ?
Cl2 O6 . 1.464(5) ?
Cl2 O8 . 1.747(5) ?
Cl3 C18 . 1.741(4) ?
N2 C6 . 1.318(4) ?
N2 C5 . 1.450(5) ?
N2 H2D . 0.8600 ?
N3 C13 . 1.330(4) ?
N3 C6 . 1.346(4) ?
N4 C13 . 1.341(4) ?
N4 C12 . 1.392(4) ?
N4 H4C . 0.8600 ?
N5 C13 . 1.338(4) ?
N5 N6 . 1.379(4) ?
N5 H5C . 0.8600 ?
N6 C14 . 1.272(4) ?
C1 N1 . 1.517(7) ?
C1 H1B . 0.9600 ?
C1 H1C . 0.9600 ?
C1 H1D . 0.9600 ?
C2 N1 . 1.430(16) ?
C2 H2A . 0.9600 ?
C2 H2B . 0.9600 ?
C2 H2C . 0.9600 ?
N1 C3 . 1.465(6) ?
N1 H1A . 0.9100 ?
C3 C4 . 1.510(7) ?
C3 H3A . 0.9700 ?
C3 H3B . 0.9700 ?
C4 C5 . 1.620(7) ?
C4 H4A . 0.9700 ?
C4 H4B . 0.9700 ?
C5 H5A . 0.9700 ?
C5 H5B . 0.9700 ?
C1' H1'B . 0.9600 ?
C1' H1'C . 0.9600 ?
C1' H1'D . 0.9600 ?
C2' H2'A . 0.9600 ?
C2' H2'B . 0.9600 ?
C2' H2'C . 0.9600 ?
C3' C4' . 1.538(10) ?
C3' H3'A . 0.9700 ?
C3' H3'B . 0.9700 ?
C4' H4'A . 0.9700 ?
C4' H4'B . 0.9700 ?
C6 C7 . 1.461(5) ?
C7 C12 . 1.398(5) ?
C7 C8 . 1.400(5) ?
C8 C9 . 1.374(5) ?
C8 H8 . 0.9300 ?
C9 C10 . 1.382(6) ?
C9 H9 . 0.9300 ?
C10 C11 . 1.384(6) ?
C10 H10 . 0.9300 ?
C11 C12 . 1.404(5) ?
C11 H11 . 0.9300 ?
C14 C15 . 1.450(5) ?
C14 H14 . 0.9300 ?
C15 C20 . 1.400(5) ?
C15 C16 . 1.404(5) ?
C16 C17 . 1.372(5) ?
C16 H16 . 0.9300 ?
C17 C18 . 1.386(5) ?
C17 H17 . 0.9300 ?
C18 C19 . 1.375(5) ?
C19 C20 . 1.378(5) ?
C19 H19 . 0.9300 ?
C20 H20 . 0.9300 ?
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O3 Cl1 O2 . . 110.00(19) ?
O3 Cl1 O1 . . 114.28(17) ?
O2 Cl1 O1 . . 112.44(19) ?
O3 Cl1 O4 . . 107.1(2) ?
O2 Cl1 O4 . . 106.45(18) ?
O1 Cl1 O4 . . 106.02(19) ?
O5 Cl2 O7 . . 110.7(3) ?
O5 Cl2 O6 . . 116.7(5) ?
O7 Cl2 O6 . . 110.9(3) ?
O5 Cl2 O8 . . 105.3(3) ?
O7 Cl2 O8 . . 107.5(2) ?
O6 Cl2 O8 . . 105.0(3) ?
C6 N2 C5 . . 122.3(3) ?
C6 N2 H2D . . 118.8 ?
C5 N2 H2D . . 118.8 ?
C13 N3 C6 . . 119.0(3) ?
C13 N4 C12 . . 120.5(3) ?
C13 N4 H4C . . 119.7 ?
C12 N4 H4C . . 119.7 ?
C13 N5 N6 . . 119.2(3) ?
C13 N5 H5C . . 120.4 ?
N6 N5 H5C . . 120.4 ?
C14 N6 N5 . . 116.2(3) ?
N1 C1 H1B . . 109.5 ?
N1 C1 H1C . . 109.5 ?
H1B C1 H1C . . 109.5 ?
N1 C1 H1D . . 109.5 ?
H1B C1 H1D . . 109.5 ?
H1C C1 H1D . . 109.5 ?
N1 C2 H2A . . 109.5 ?
N1 C2 H2B . . 109.5 ?
H2A C2 H2B . . 109.5 ?
N1 C2 H2C . . 109.5 ?
H2A C2 H2C . . 109.5 ?
H2B C2 H2C . . 109.5 ?
C2 N1 C3 . . 123.2(6) ?
C2 N1 C1 . . 109.2(6) ?
C3 N1 C1 . . 97.5(5) ?
C2 N1 H1A . . 108.6 ?
C3 N1 H1A . . 108.6 ?
C1 N1 H1A . . 108.6 ?
N1 C3 C4 . . 106.3(5) ?
N1 C3 H3A . . 110.5 ?
C4 C3 H3A . . 110.5 ?
N1 C3 H3B . . 110.5 ?
C4 C3 H3B . . 110.5 ?
H3A C3 H3B . . 108.7 ?
C3 C4 C5 . . 113.7(5) ?
C3 C4 H4A . . 108.8 ?
C5 C4 H4A . . 108.8 ?
C3 C4 H4B . . 108.8 ?
C5 C4 H4B . . 108.8 ?
H4A C4 H4B . . 107.7 ?
N2 C5 C4 . . 106.7(4) ?
N2 C5 H5A . . 110.4 ?
C4 C5 H5A . . 110.4 ?
N2 C5 H5B . . 110.4 ?
C4 C5 H5B . . 110.4 ?
H5A C5 H5B . . 108.6 ?
H1'B C1' H1'C . . 109.5 ?
H1'B C1' H1'D . . 109.5 ?
H1'C C1' H1'D . . 109.5 ?
H2'A C2' H2'B . . 109.5 ?
H2'A C2' H2'C . . 109.5 ?
H2'B C2' H2'C . . 109.5 ?
C4' C3' H3'A . . 109.0 ?
C4' C3' H3'B . . 109.0 ?
H3'A C3' H3'B . . 107.8 ?
C3' C4' H4'A . . 110.6 ?
C3' C4' H4'B . . 110.6 ?
H4'A C4' H4'B . . 108.7 ?
N2 C6 N3 . . 117.7(3) ?
N2 C6 C7 . . 120.5(3) ?
N3 C6 C7 . . 121.8(3) ?
C12 C7 C8 . . 119.3(3) ?
C12 C7 C6 . . 115.8(3) ?
C8 C7 C6 . . 124.8(3) ?
C9 C8 C7 . . 120.7(4) ?
C9 C8 H8 . . 119.6 ?
C7 C8 H8 . . 119.6 ?
C8 C9 C10 . . 119.7(4) ?
C8 C9 H9 . . 120.1 ?
C10 C9 H9 . . 120.1 ?
C9 C10 C11 . . 121.2(4) ?
C9 C10 H10 . . 119.4 ?
C11 C10 H10 . . 119.4 ?
C10 C11 C12 . . 119.2(4) ?
C10 C11 H11 . . 120.4 ?
C12 C11 H11 . . 120.4 ?
N4 C12 C7 . . 119.5(3) ?
N4 C12 C11 . . 120.8(3) ?
C7 C12 C11 . . 119.8(3) ?
N3 C13 N5 . . 116.5(3) ?
N3 C13 N4 . . 123.4(3) ?
N5 C13 N4 . . 120.1(3) ?
N6 C14 C15 . . 120.7(3) ?
N6 C14 H14 . . 119.6 ?
C15 C14 H14 . . 119.6 ?
C20 C15 C16 . . 118.6(3) ?
C20 C15 C14 . . 120.6(3) ?
C16 C15 C14 . . 120.8(3) ?
C17 C16 C15 . . 120.1(3) ?
C17 C16 H16 . . 119.9 ?
C15 C16 H16 . . 119.9 ?
C16 C17 C18 . . 119.4(3) ?
C16 C17 H17 . . 120.3 ?
C18 C17 H17 . . 120.3 ?
C19 C18 C17 . . 122.2(3) ?
C19 C18 Cl3 . . 118.9(3) ?
C17 C18 Cl3 . . 119.0(3) ?
C18 C19 C20 . . 118.2(3) ?
C18 C19 H19 . . 120.9 ?
C20 C19 H19 . . 120.9 ?
C19 C20 C15 . . 121.5(3) ?
C19 C20 H20 . . 119.3 ?
C15 C20 H20 . . 119.3 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
N1 H1A O3 . 0.91 2.19 2.990(5) 146.7
N5 H5C O2 . 0.86 2.11 2.922(4) 156.8
N4 H4C O1 2_565 0.86 2.14 2.964(4) 159.6
N2 H2D O7 . 0.86 2.10 2.873(5) 148.9
C19 H19 O2 2_575 0.93 2.48 3.316(5) 149.7
C1 H1D O6 1_565 0.96 2.56 3.445(8) 153.1
C1 H1C O6 2_666 0.96 2.62 3.555(10) 165.6
_iucr_refine_instructions_details
;
TITL 1 in P-1
CELL 0.71073 10.4533 10.5018 12.6258 104.745 91.146 96.210
ZERR 2.00 0.0018 0.0018 0.0023 0.009 0.010 0.010
LATT 1
SFAC C H N O Cl
UNIT 40 50 12 16 6
OMIT -5 1 1
OMIT -2 3 3
OMIT -3 4 0
OMIT -4 4 0
OMIT -1 3 0
OMIT 1 4 4
OMIT -4 -2 4
OMIT 3 -2 3
OMIT 4 -1 3
OMIT -4 1 2
OMIT -1 -1 6
OMIT 3 2 0
OMIT 1 -3 4
OMIT -2 -2 3
OMIT -3 3 1
OMIT 3 -3 3
OMIT 0 1 6
OMIT -3 3 3
OMIT 0 3 2
OMIT -3 -3 2
OMIT -3 5 3
OMIT 7 -6 6
OMIT 2 0 2
OMIT 3 -5 2
OMIT -2 -4 6
OMIT 0 -5 4
OMIT 5 -2 5
OMIT 3 2 1
OMIT 5 0 3
OMIT 4 -4 2
OMIT -4 4 1
OMIT -5 3 4
OMIT -1 -1 1
OMIT 3 4 2
OMIT -4 1 3
OMIT 6 -2 2
OMIT 6 0 2
OMIT 6 -4 1
OMIT -1 4 5
OMIT 5 -1 4
OMIT -8 8 3
OMIT -1 -2 6
OMIT -9 1 3
OMIT -4 4 2
OMIT 8 -6 2
OMIT 3 -1 6
OMIT 3 -2 5
OMIT 8 -5 5
OMIT 3 -2 1
OMIT 6 -5 4
OMIT 0.00 51.00
L.S. 8
ACTA
BOND $H
FMAP 2
PLAN 20
DFIX 1.45 0.01 N1 C3 N1' C3' C1 N1 C1' N1'
DFIX 1.53 0.01 C3 C4 C4 C5 C3' C4' C4' C5'
ISOR 0.01 C4' C1' C4 N1 N1'
EADP C5 C5'
EXYZ C5 C5'
EADP N1 N1'
EXYZ N1 N1'
HTAB N2 O7
HTAB N4 O1_$1
EQIV $1 -x, -y+1, -z
HTAB N5 O2
HTAB N1 O3
size 0.25 0.23 0.18
SIMU C4 C4'
DELU C4 C4'
SIMU C3 C3'
DELU C3 C3'
SIMU C2 C2'
DELU C2 C2'
SIMU C1 C1'
DELU C1 C1'
WGHT 0.133900 1.068900
FVAR 0.592640 0.767670
Cl1 5 0.329411 0.742528 0.100020 11.000000 0.042350 0.037880 =
0.046770 0.009850 -0.003940 -0.004790
Cl2 5 0.263735 0.251357 0.612778 11.000000 0.054250 0.081870 =
0.047380 0.011640 -0.001090 -0.014130
Cl3 5 -0.497017 0.781621 -0.259238 11.000000 0.068820 0.075910 =
0.066550 0.021590 -0.030220 0.009600
N2 3 0.218187 0.422565 0.384038 11.000000 0.043640 0.042890 =
0.051320 0.016530 -0.012770 0.003030
AFIX 43
H2D 2 0.221324 0.360228 0.416588 11.000000 -1.200000
AFIX 0
N3 3 0.112111 0.519682 0.271845 11.000000 0.036320 0.039040 =
0.040640 0.008630 -0.004870 0.004400
N4 3 -0.077136 0.411695 0.169721 11.000000 0.035340 0.042000 =
0.036880 0.011940 -0.005810 0.002570
AFIX 43
H4C 2 -0.137942 0.413534 0.123424 11.000000 -1.200000
AFIX 0
N5 3 0.015780 0.617215 0.155464 11.000000 0.033770 0.043160 =
0.043550 0.014350 -0.007070 0.001950
AFIX 43
H5C 2 0.078054 0.680564 0.170954 11.000000 -1.200000
AFIX 0
N6 3 -0.085542 0.620910 0.085093 11.000000 0.032860 0.040970 =
0.037510 0.011860 -0.005090 0.004070
O1 4 0.300074 0.654331 -0.008781 11.000000 0.065880 0.048570 =
0.045490 0.007190 -0.015320 -0.004850
O2 4 0.224500 0.819233 0.139513 11.000000 0.043300 0.048050 =
0.089780 0.012360 0.012010 -0.000430
O3 4 0.369236 0.677678 0.181099 11.000000 0.068490 0.053230 =
0.052760 0.017800 -0.013780 -0.000340
O4 4 0.461126 0.858080 0.086463 11.000000 0.080930 0.082160 =
0.125880 0.007690 0.023980 -0.015800
O5 4 0.132387 0.270777 0.608160 11.000000 0.042340 0.408030 =
0.098030 -0.026290 -0.017110 0.006870
O6 4 0.293023 0.127276 0.635241 11.000000 0.222170 0.057720 =
0.083540 0.028550 0.008520 -0.028630
O7 4 0.324799 0.271105 0.516957 11.000000 0.091630 0.086000 =
0.053440 0.031260 0.015500 0.027790
O8 4 0.333286 0.376151 0.724715 11.000000 0.090940 0.110910 =
0.102330 -0.001020 -0.007940 0.006450
PART 1
C1 1 0.378968 0.931352 0.390417 21.000000 0.047260 0.133230 =
0.067180 -0.034030 -0.014770 0.005960
AFIX 33
H1B 2 0.355124 0.966339 0.330574 21.000000 -1.500000
H1C 2 0.461179 0.898729 0.378297 21.000000 -1.500000
H1D 2 0.384250 1.000127 0.457584 21.000000 -1.500000
AFIX 0
C2 1 0.153358 0.862324 0.398333 21.000000 0.064200 0.042480 =
0.051170 0.001770 -0.003130 0.010760
AFIX 33
H2A 2 0.089449 0.791479 0.403291 21.000000 -1.500000
H2B 2 0.137341 0.887667 0.331832 21.000000 -1.500000
H2C 2 0.149323 0.936954 0.460103 21.000000 -1.500000
AFIX 0
N1 3 0.278396 0.818946 0.397994 21.000000 0.095890 0.074120 =
0.041610 -0.001340 -0.008160 0.043810
AFIX 13
H1A 2 0.281806 0.750046 0.337873 21.000000 -1.200000
AFIX 0
C3 1 0.337951 0.786641 0.492454 21.000000 0.077890 0.074920 =
0.054130 0.005860 -0.010830 0.007950
AFIX 23
H3A 2 0.325188 0.852554 0.559568 21.000000 -1.200000
H3B 2 0.429740 0.783925 0.484134 21.000000 -1.200000
AFIX 0
C4 1 0.272881 0.652238 0.495722 21.000000 0.094960 0.088570 =
0.037140 0.010800 -0.012140 -0.045480
AFIX 23
H4A 2 0.180690 0.650375 0.483638 21.000000 -1.200000
H4B 2 0.288060 0.639741 0.568254 21.000000 -1.200000
AFIX 0
C5 1 0.322221 0.530264 0.405708 21.000000 0.064220 0.055980 =
0.072220 0.030870 -0.033770 -0.012350
AFIX 23
H5A 2 0.342318 0.556296 0.338966 21.000000 -1.200000
H5B 2 0.399003 0.503280 0.433955 21.000000 -1.200000
PART 2
AFIX 0
C1' 1 0.401427 0.884720 0.437650 -21.000000 0.094120 0.083120 =
0.078700 0.048220 -0.000590 0.007400
AFIX 33
H1'B 2 0.461204 0.820640 0.433928 -21.000000 -1.500000
H1'C 2 0.397183 0.934604 0.512373 -21.000000 -1.500000
H1'D 2 0.429664 0.943702 0.393649 -21.000000 -1.500000
AFIX 0
C2' 1 0.155810 0.895884 0.397131 -21.000000 0.036710 0.009380 =
0.124260 0.004680 0.014960 0.001000
AFIX 33
H2'A 2 0.167567 0.951809 0.347801 -21.000000 -1.500000
H2'B 2 0.145244 0.949245 0.469689 -21.000000 -1.500000
H2'C 2 0.080528 0.833099 0.373380 -21.000000 -1.500000
AFIX 0
N1' 3 0.278396 0.818946 0.397994 -21.000000 0.095890 0.074120 =
0.041610 -0.001340 -0.008160 0.043810
AFIX 13
H1'A 2 0.284393 0.762836 0.330712 -21.000000 -1.200000
AFIX 0
C3' 1 0.239961 0.737893 0.481097 -21.000000 0.025830 0.015610 =
0.028640 -0.008920 -0.003280 -0.008160
AFIX 23
H3'A 2 0.225893 0.798348 0.550841 -21.000000 -1.200000
H3'B 2 0.159393 0.682472 0.455233 -21.000000 -1.200000
AFIX 0
C4' 1 0.342477 0.649694 0.498572 -21.000000 0.015750 0.052290 =
0.027900 0.012610 -0.016320 -0.017830
AFIX 23
H4'A 2 0.428344 0.695443 0.499242 -21.000000 -1.200000
H4'B 2 0.332014 0.626068 0.567591 -21.000000 -1.200000
AFIX 0
C5' 1 0.322221 0.530264 0.405708 -21.000000 0.064220 0.055980 =
0.072220 0.030870 -0.033770 -0.012350
AFIX 23
H5'A 2 0.322886 0.563446 0.340681 -21.000000 -1.200000
H5'B 2 0.400312 0.488055 0.405611 -21.000000 -1.200000
PART 0
AFIX 0
C6 1 0.118979 0.416784 0.316237 11.000000 0.039780 0.039240 =
0.034540 0.009550 -0.000990 0.007740
C7 1 0.021464 0.301337 0.290064 11.000000 0.037730 0.040520 =
0.034850 0.010010 -0.000280 0.004090
C8 1 0.023528 0.190251 0.331917 11.000000 0.049550 0.048760 =
0.048550 0.019840 -0.001820 0.006780
AFIX 43
H8 2 0.088134 0.189063 0.383260 11.000000 -1.200000
AFIX 0
C9 1 -0.068832 0.082952 0.297989 11.000000 0.054710 0.048220 =
0.057030 0.021990 0.000970 0.000100
AFIX 43
H9 2 -0.066263 0.009260 0.325764 11.000000 -1.200000
AFIX 0
C10 1 -0.165546 0.084991 0.222431 11.000000 0.054170 0.045750 =
0.058890 0.016170 -0.000870 -0.007370
AFIX 43
H10 2 -0.227870 0.012141 0.199766 11.000000 -1.200000
AFIX 0
C11 1 -0.171380 0.193485 0.179843 11.000000 0.045510 0.053570 =
0.047420 0.016900 -0.008100 -0.004670
AFIX 43
H11 2 -0.237541 0.194043 0.129668 11.000000 -1.200000
AFIX 0
C12 1 -0.076315 0.302623 0.213250 11.000000 0.037390 0.039970 =
0.037460 0.010230 0.002730 0.001990
C13 1 0.016101 0.513919 0.199380 11.000000 0.035320 0.037920 =
0.033300 0.008850 0.000610 0.008480
C14 1 -0.083079 0.724307 0.049825 11.000000 0.037180 0.038490 =
0.042780 0.010240 -0.005550 0.001800
AFIX 43
H14 2 -0.015368 0.791810 0.072224 11.000000 -1.200000
AFIX 0
C15 1 -0.184728 0.738026 -0.024932 11.000000 0.039400 0.034710 =
0.037900 0.007340 -0.001410 0.006520
C16 1 -0.290416 0.639730 -0.056882 11.000000 0.047490 0.033720 =
0.044920 0.009070 -0.005370 0.003140
AFIX 43
H16 2 -0.296350 0.565394 -0.029187 11.000000 -1.200000
AFIX 0
C17 1 -0.384959 0.653207 -0.128916 11.000000 0.049430 0.039190 =
0.049160 0.003660 -0.010790 0.001050
AFIX 43
H17 2 -0.454728 0.587955 -0.150631 11.000000 -1.200000
AFIX 0
C18 1 -0.375571 0.764915 -0.169033 11.000000 0.043720 0.050830 =
0.035740 0.005850 -0.006850 0.012850
C19 1 -0.273949 0.863541 -0.139289 11.000000 0.052050 0.043150 =
0.049670 0.020590 -0.001620 0.010240
AFIX 43
H19 2 -0.268934 0.937367 -0.167619 11.000000 -1.200000
AFIX 0
C20 1 -0.179760 0.850015 -0.066374 11.000000 0.039990 0.036720 =
0.055530 0.015470 -0.003520 0.001730
AFIX 43
H20 2 -0.111339 0.916757 -0.044174 11.000000 -1.200000
AFIX 0
Q1 1 0.229600 0.723200 0.499400 11.000000 0.050000 0.69
Q2 1 0.202600 0.154800 0.627900 11.000000 0.050000 0.64
Q3 1 0.205800 0.299600 0.601800 11.000000 0.050000 0.64
Q4 1 0.128200 0.223000 0.621700 11.000000 0.050000 0.57
Q5 1 0.406700 0.963200 0.391600 11.000000 0.050000 0.55
Q6 1 0.347700 0.608700 0.480400 11.000000 0.050000 0.54
Q7 1 0.484300 0.931600 0.171100 11.000000 0.050000 0.45
Q8 1 0.331800 0.486900 0.703500 11.000000 0.050000 0.43
Q9 1 0.143900 0.352600 0.606300 11.000000 0.050000 0.41
Q10 1 0.549900 0.801100 0.054000 11.000000 0.050000 0.40
Q11 1 0.267600 0.371500 0.803300 11.000000 0.050000 0.37
Q12 1 0.441800 0.359200 0.736000 11.000000 0.050000 0.37
Q13 1 -0.435200 0.814700 -0.280200 11.000000 0.050000 0.33
Q14 1 0.356800 0.864700 0.416300 11.000000 0.050000 0.31
Q15 1 0.070000 0.343600 0.299600 11.000000 0.050000 0.30
Q16 1 0.314900 0.856700 0.401400 11.000000 0.050000 0.30
Q17 1 0.436800 0.896000 0.006500 11.000000 0.050000 0.29
Q18 1 0.403800 0.267200 0.536700 11.000000 0.050000 0.27
Q19 1 0.161600 0.933400 0.420400 11.000000 0.050000 0.24
Q20 1 0.336400 0.531900 0.374900 11.000000 0.050000 0.24
HKLF 4
END
;
data_global
_journal_date_recd_electronic 2012-03-06
_journal_date_accepted 2012-04-24
_journal_name_full 'Acta Crystallographica, Section E'
_journal_year 2012
_journal_volume 68
_journal_issue 5
_journal_page_first o1557
_journal_page_last o1558
_journal_paper_category QO
_journal_paper_doi 10.1107/S1600536812018272
_journal_coeditor_code IM2363
_publ_contact_author_name 'Xin Zhai'
_publ_contact_author_address
;
Key Laboratory of Original New Drug Design and Discovery of the
Ministry of Education, Shenyang Pharmaceutical University, Shenyang,
Liaoning 110016, People's Republic of China
;
_publ_contact_author_email 'leixinjia@126.com'
_publ_contact_author_fax '86-24-23986429'
_publ_contact_author_phone '86-24-23986429'
_publ_section_title
;\
(E)-2-[2-(4-Chlorobenzylidene)hydrazin-1-yl]-4-{[3-(dimethylazaniumyl)\
propyl]amino}quinazolin-1-ium bis(perchlorate)
;
loop_
_publ_author_name
_publ_author_address
'Nan Jiang'
;
Key Laboratory of Original New Drug Design and Discovery of the
Ministry of Education, Shenyang Pharmaceutical University, Shenyang,
Liaoning 110016, People's Republic of China
;
'Jian Zuo'
;
Key Laboratory of Marine Chemistry Theory and Technology,
Ministry of Education, College of Chemistry and Chemical Engineering,
Ocean University of China, Qingdao, Shandong 266100,
People's Republic of China
;
'Haiyan Wang'
;
Key Laboratory of Original New Drug Design and Discovery of the
Ministry of Education, Shenyang Pharmaceutical University, Shenyang,
Liaoning 110016, People's Republic of China
;
'Ming Han'
;
Key Laboratory of Original New Drug Design and Discovery of the
Ministry of Education, Shenyang Pharmaceutical University, Shenyang,
Liaoning 110016, People's Republic of China
;
'Xin Zhai'
;
Key Laboratory of Original New Drug Design and Discovery of the
Ministry of Education, Shenyang Pharmaceutical University, Shenyang,
Liaoning 110016, People's Republic of China
;