##############################################################################
# #
# 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
;
cis-Bis[(4-nitrophenyl)cyanamido-\kN^1^]bis(1,10-phenanthroline-
\k^2^N,N')nickel(II) methanol monosolvate
;
_chemical_name_common ?
_chemical_formula_moiety 'C38 H24 N10 Ni O4, C H4 O'
_chemical_formula_sum 'C39 H28 N10 Ni O5 '
_chemical_formula_iupac '[Ni (C7 H4 N3 O2)2 (C12 H8 N2)2], C H4 O'
_chemical_formula_weight 775.40
_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 10.019(2)
_cell_length_b 11.307(2)
_cell_length_c 16.403(3)
_cell_angle_alpha 103.54(3)
_cell_angle_beta 92.96(3)
_cell_angle_gamma 99.77(3)
_cell_volume 1772.3(7)
_cell_formula_units_Z 2
_cell_measurement_reflns_used 9512
_cell_measurement_theta_min 2.07
_cell_measurement_theta_max 29.18
_cell_measurement_temperature 298(2)
_exptl_crystal_description plate
_exptl_crystal_colour yellow
_exptl_crystal_size_max 0.25
_exptl_crystal_size_mid 0.2
_exptl_crystal_size_min 0.1
_exptl_crystal_density_diffrn 1.453
_exptl_crystal_density_meas ?
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 800
_exptl_absorpt_coefficient_mu 0.609
_exptl_absorpt_correction_type numerical
_exptl_absorpt_process_details
'(X-RED and X-SHAPE; Stoe & Cie, 2005)'
_exptl_absorpt_correction_T_min 0.862
_exptl_absorpt_correction_T_max 0.938
_exptl_special_details
; shape of crystal determined optically
;
_diffrn_ambient_temperature 298(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 'Stoe IPDS II'
_diffrn_measurement_method 'rotation method'
_diffrn_detector_area_resol_mean '0.15 mm'
_diffrn_reflns_number 19823
_diffrn_reflns_av_R_equivalents 0.0526
_diffrn_reflns_av_sigmaI/netI 0.0538
_diffrn_reflns_theta_min 2.07
_diffrn_reflns_theta_max 29.18
_diffrn_reflns_theta_full 29.18
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_limit_h_min -12
_diffrn_reflns_limit_h_max 13
_diffrn_reflns_limit_k_min -15
_diffrn_reflns_limit_k_max 15
_diffrn_reflns_limit_l_min -22
_diffrn_reflns_limit_l_max 20
_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 9512
_reflns_number_gt 6693
_reflns_threshold_expression I>2\s(I)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_R_factor_all 0.0951
_refine_ls_R_factor_gt 0.0605
_refine_ls_wR_factor_gt 0.1250
_refine_ls_wR_factor_ref 0.1393
_refine_ls_goodness_of_fit_ref 1.060
_refine_ls_restrained_S_all 1.060
_refine_ls_number_reflns 9512
_refine_ls_number_parameters 501
_refine_ls_number_restraints 1
_refine_ls_hydrogen_treatment mixed
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0512P)^2^+0.8996P] 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 0.001
_refine_ls_shift/su_mean 0.000
_refine_diff_density_max 0.654
_refine_diff_density_min -0.311
_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'
'Ni' 'Ni' 0.3393 1.1124
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_computing_data_collection 'X-AREA (Stoe & Cie, 2005)'
_computing_cell_refinement 'X-AREA (Stoe & Cie, 2005)'
_computing_data_reduction 'X-AREA (Stoe & Cie, 2005)'
_computing_structure_solution 'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)'
_computing_molecular_graphics 'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material 'WinGX (Farrugia, 1999)'
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
C C39 0.1500(7) 0.3400(5) 0.7660(5) 0.146(3) Uani d . 1 1 . .
H H39A 0.2378 0.3493 0.7450 0.219 Uiso calc R 1 1 . .
H H39B 0.1205 0.2554 0.7678 0.219 Uiso calc R 1 1 . .
H H39C 0.1557 0.3928 0.8217 0.219 Uiso calc R 1 1 . .
O O1 0.8551(5) 0.7156(4) 1.0013(4) 0.197(3) Uani d . 1 1 . .
O O2 1.0049(4) 0.6144(4) 0.9548(3) 0.1357(15) Uani d . 1 1 . .
Ni Ni1 0.62348(4) -0.11112(3) 0.714358(19) 0.04018(11) Uani d . 1 1 . .
N N2 0.7128(2) -0.2733(2) 0.68911(13) 0.0435(5) Uani d . 1 1 . .
N N3 0.4682(2) -0.2034(2) 0.77044(14) 0.0484(5) Uani d . 1 1 . .
N N1 0.5513(2) -0.1913(2) 0.58779(13) 0.0449(5) Uani d . 1 1 . .
N N4 0.7020(2) -0.0547(2) 0.83983(13) 0.0445(5) Uani d . 1 1 . .
N N8 0.7899(3) -0.0105(3) 0.67656(16) 0.0583(6) Uani d . 1 1 . .
N N5 0.5203(3) 0.0329(2) 0.72202(17) 0.0590(6) Uani d . 1 1 . .
C C12 0.6933(3) -0.3347(2) 0.60642(15) 0.0418(5) Uani d . 1 1 . .
C C5 0.5907(3) -0.3441(3) 0.46523(17) 0.0538(7) Uani d . 1 1 . .
C C24 0.6222(3) -0.1045(3) 0.89187(16) 0.0469(6) Uani d . 1 1 . .
C C13 0.4963(3) -0.1838(3) 0.85447(17) 0.0490(6) Uani d . 1 1 . .
C C11 0.7872(3) -0.3163(3) 0.74050(18) 0.0532(7) Uani d . 1 1 . .
H H11 0.8019 -0.2746 0.7972 0.064 Uiso calc R 1 1 . .
C C20 0.6575(4) -0.0808(3) 0.97889(18) 0.0628(9) Uani d . 1 1 . .
C C6 0.6549(4) -0.4473(3) 0.4333(2) 0.0713(10) Uani d . 1 1 . .
H H6 0.6451 -0.4833 0.3757 0.086 Uiso calc R 1 1 . .
C C1 0.6097(3) -0.2884(2) 0.55207(15) 0.0438(6) Uani d . 1 1 . .
N N9 0.8915(3) 0.1479(2) 0.60677(15) 0.0534(6) Uani d . 1 1 . .
C C38 0.8241(3) 0.0062(3) 0.46698(18) 0.0505(6) Uani d . 1 1 . .
H H38 0.7834 -0.0565 0.4906 0.061 Uiso calc R 1 1 . .
C C22 0.8588(4) 0.0513(3) 0.9591(2) 0.0735(10) Uani d . 1 1 . .
H H22 0.9395 0.1066 0.9805 0.088 Uiso calc R 1 1 . .
C C33 0.8870(3) 0.1206(3) 0.51983(17) 0.0460(6) Uani d . 1 1 . .
C C8 0.7502(3) -0.4389(3) 0.57381(19) 0.0540(7) Uani d . 1 1 . .
C C14 0.3505(3) -0.2741(3) 0.7350(2) 0.0651(9) Uani d . 1 1 . .
H H14 0.3292 -0.2865 0.6774 0.078 Uiso calc R 1 1 . .
C C32 0.8361(3) 0.0614(3) 0.64100(17) 0.0486(6) Uani d . 1 1 . .
C C36 0.8833(3) 0.0780(3) 0.34610(17) 0.0502(6) Uani d . 1 1 . .
C C35 0.9464(3) 0.1919(3) 0.39645(19) 0.0571(7) Uani d . 1 1 . .
H H35 0.9871 0.2539 0.3722 0.069 Uiso calc R 1 1 . .
C C34 0.9486(3) 0.2129(3) 0.48241(19) 0.0546(7) Uani d . 1 1 . .
H H34 0.9915 0.2893 0.5163 0.065 Uiso calc R 1 1 . .
C C37 0.8216(3) -0.0150(3) 0.38064(18) 0.0532(7) Uani d . 1 1 . .
H H37 0.7790 -0.0911 0.3461 0.064 Uiso calc R 1 1 . .
C C23 0.8176(3) 0.0209(3) 0.87307(19) 0.0561(7) Uani d . 1 1 . .
H H23 0.8735 0.0551 0.8377 0.067 Uiso calc R 1 1 . .
C C2 0.4720(3) -0.1491(3) 0.53848(19) 0.0578(7) Uani d . 1 1 . .
H H2 0.4306 -0.0834 0.5627 0.069 Uiso calc R 1 1 . .
C C3 0.4480(4) -0.1994(3) 0.4516(2) 0.0665(9) Uani d . 1 1 . .
H H3 0.3917 -0.1674 0.4189 0.080 Uiso calc R 1 1 . .
C C19 0.5667(6) -0.1375(4) 1.0287(2) 0.0860(13) Uani d . 1 1 . .
H H19 0.5901 -0.1234 1.0862 0.103 Uiso calc R 1 1 . .
C C9 0.8266(4) -0.4821(3) 0.6308(2) 0.0634(8) Uani d . 1 1 . .
H H9 0.8647 -0.5520 0.6121 0.076 Uiso calc R 1 1 . .
C C21 0.7808(5) 0.0001(4) 1.0112(2) 0.0774(11) Uani d . 1 1 . .
H H21 0.8089 0.0185 1.0685 0.093 Uiso calc R 1 1 . .
C C17 0.4077(4) -0.2368(3) 0.9054(2) 0.0660(9) Uani d . 1 1 . .
C C10 0.8445(4) -0.4207(3) 0.7137(2) 0.0625(8) Uani d . 1 1 . .
H H10 0.8948 -0.4486 0.7522 0.075 Uiso calc R 1 1 . .
O O3 0.9376(3) 0.1389(3) 0.22532(15) 0.0832(8) Uani d . 1 1 . .
N N10 0.8849(3) 0.0551(3) 0.25539(16) 0.0626(7) Uani d . 1 1 . .
O O4 0.8363(4) -0.0475(3) 0.21191(16) 0.1014(10) Uani d . 1 1 . .
C C4 0.5077(4) -0.2955(3) 0.41506(18) 0.0659(9) Uani d . 1 1 . .
H H4 0.4936 -0.3287 0.3571 0.079 Uiso calc R 1 1 . .
C C7 0.7291(4) -0.4929(3) 0.4848(2) 0.0706(9) Uani d . 1 1 . .
H H7 0.7677 -0.5612 0.4622 0.085 Uiso calc R 1 1 . .
C C18 0.4481(6) -0.2108(4) 0.9942(3) 0.0871(14) Uani d . 1 1 . .
H H18 0.3906 -0.2458 1.0285 0.104 Uiso calc R 1 1 . .
C C15 0.2576(4) -0.3304(4) 0.7812(4) 0.0866(13) Uani d . 1 1 . .
H H15 0.1766 -0.3807 0.7544 0.104 Uiso calc R 1 1 . .
C C16 0.2862(4) -0.3115(4) 0.8657(3) 0.0862(13) Uani d . 1 1 . .
H H16 0.2244 -0.3485 0.8970 0.103 Uiso calc R 1 1 . .
N N6 0.4741(3) 0.2393(2) 0.78229(17) 0.0612(7) Uani d . 1 1 . .
C C25 0.5024(3) 0.1317(3) 0.75123(17) 0.0502(7) Uani d . 1 1 . .
C C26 0.5794(3) 0.3316(3) 0.82375(18) 0.0535(7) Uani d . 1 1 . .
C C31 0.7151(4) 0.3199(3) 0.8274(2) 0.0640(8) Uani d . 1 1 . .
H H31 0.7387 0.2463 0.7986 0.077 Uiso calc R 1 1 . .
C C30 0.8150(4) 0.4140(3) 0.8722(3) 0.0731(10) Uani d . 1 1 . .
H H30 0.9053 0.4043 0.8742 0.088 Uiso calc R 1 1 . .
C C29 0.7803(4) 0.5236(3) 0.9144(2) 0.0706(9) Uani d . 1 1 . .
C C27 0.5480(4) 0.4449(3) 0.8667(3) 0.0801(11) Uani d . 1 1 . .
H H27 0.4581 0.4561 0.8646 0.096 Uiso calc R 1 1 . .
N N7 0.8870(5) 0.6246(4) 0.9598(3) 0.1013(12) Uani d . 1 1 . .
C C28 0.6476(5) 0.5385(4) 0.9115(3) 0.0856(12) Uani d . 1 1 . .
H H28 0.6253 0.6127 0.9401 0.103 Uiso calc R 1 1 . .
O O5 0.0518(4) 0.3745(3) 0.7102(3) 0.1121(12) Uani d D 1 1 . .
H H5A 0.001(5) 0.301(4) 0.681(3) 0.14(2) Uiso d D 1 1 . .
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
C39 0.175(6) 0.078(3) 0.169(6) 0.031(4) -0.033(5) 0.007(4)
O1 0.132(4) 0.093(3) 0.301(7) 0.003(3) -0.012(4) -0.062(4)
O2 0.088(2) 0.105(3) 0.196(4) -0.015(2) 0.031(3) 0.020(3)
Ni1 0.0489(2) 0.04276(18) 0.02925(15) 0.01033(14) 0.00388(12) 0.00828(12)
N2 0.0498(13) 0.0472(12) 0.0352(10) 0.0105(10) 0.0052(9) 0.0125(9)
N3 0.0533(14) 0.0422(12) 0.0478(12) 0.0082(10) 0.0090(10) 0.0071(10)
N1 0.0528(13) 0.0485(12) 0.0353(10) 0.0150(10) 0.0015(9) 0.0106(9)
N4 0.0549(13) 0.0440(12) 0.0337(10) 0.0103(10) 0.0015(9) 0.0075(9)
N8 0.0629(16) 0.0673(16) 0.0467(13) 0.0077(13) 0.0109(11) 0.0199(12)
N5 0.0680(17) 0.0530(15) 0.0569(15) 0.0198(13) 0.0024(12) 0.0099(12)
C12 0.0457(14) 0.0413(13) 0.0382(12) 0.0080(11) 0.0069(10) 0.0091(10)
C5 0.0667(19) 0.0549(17) 0.0357(13) 0.0074(14) 0.0038(12) 0.0061(12)
C24 0.0654(18) 0.0447(14) 0.0349(12) 0.0209(13) 0.0090(12) 0.0097(10)
C13 0.0628(18) 0.0446(14) 0.0460(14) 0.0204(13) 0.0207(13) 0.0131(11)
C11 0.0613(18) 0.0604(18) 0.0442(14) 0.0168(14) 0.0043(13) 0.0219(13)
C20 0.097(3) 0.0649(19) 0.0360(14) 0.0398(19) 0.0114(15) 0.0131(13)
C6 0.100(3) 0.066(2) 0.0414(15) 0.0221(19) 0.0067(16) -0.0039(14)
C1 0.0502(15) 0.0450(14) 0.0347(12) 0.0050(11) 0.0051(10) 0.0092(10)
N9 0.0590(15) 0.0565(14) 0.0452(12) 0.0045(12) 0.0082(11) 0.0176(11)
C38 0.0542(16) 0.0490(15) 0.0496(15) 0.0060(13) 0.0079(12) 0.0168(12)
C22 0.089(3) 0.066(2) 0.0548(19) 0.0179(19) -0.0261(18) -0.0005(16)
C33 0.0447(14) 0.0527(15) 0.0444(13) 0.0121(12) 0.0077(11) 0.0163(12)
C8 0.0627(18) 0.0445(15) 0.0544(16) 0.0136(13) 0.0079(14) 0.0086(12)
C14 0.0533(18) 0.0570(19) 0.078(2) 0.0074(15) 0.0052(16) 0.0051(16)
C32 0.0472(15) 0.0584(17) 0.0404(13) 0.0120(13) 0.0062(11) 0.0110(12)
C36 0.0489(16) 0.0638(18) 0.0424(14) 0.0161(13) 0.0069(12) 0.0175(13)
C35 0.0649(19) 0.0590(18) 0.0526(16) 0.0087(15) 0.0142(14) 0.0240(14)
C34 0.0625(18) 0.0491(16) 0.0509(15) 0.0034(14) 0.0116(13) 0.0135(13)
C37 0.0540(17) 0.0546(17) 0.0494(15) 0.0075(13) 0.0041(13) 0.0115(13)
C23 0.0627(18) 0.0497(16) 0.0507(16) 0.0066(14) -0.0062(13) 0.0072(13)
C2 0.0635(19) 0.069(2) 0.0455(15) 0.0245(15) -0.0018(13) 0.0161(14)
C3 0.075(2) 0.083(2) 0.0442(16) 0.0182(18) -0.0085(15) 0.0212(16)
C19 0.132(4) 0.105(3) 0.0445(18) 0.059(3) 0.033(2) 0.033(2)
C9 0.074(2) 0.0528(18) 0.071(2) 0.0258(16) 0.0141(17) 0.0182(15)
C21 0.114(3) 0.082(2) 0.0356(15) 0.042(2) -0.0144(18) 0.0012(16)
C17 0.077(2) 0.0609(19) 0.077(2) 0.0283(18) 0.0401(18) 0.0321(17)
C10 0.070(2) 0.064(2) 0.0648(19) 0.0242(16) 0.0056(16) 0.0302(16)
O3 0.110(2) 0.0929(19) 0.0529(13) 0.0118(16) 0.0165(13) 0.0331(13)
N10 0.0711(18) 0.0763(19) 0.0446(13) 0.0176(15) 0.0061(12) 0.0204(13)
O4 0.153(3) 0.088(2) 0.0470(13) -0.0056(19) 0.0008(16) 0.0078(13)
C4 0.084(2) 0.077(2) 0.0333(13) 0.0120(19) -0.0025(14) 0.0111(14)
C7 0.095(3) 0.0550(19) 0.0598(19) 0.0275(18) 0.0138(18) -0.0008(15)
C18 0.123(4) 0.099(3) 0.073(2) 0.057(3) 0.061(3) 0.052(2)
C15 0.053(2) 0.069(2) 0.133(4) 0.0011(17) 0.020(2) 0.020(2)
C16 0.076(3) 0.074(2) 0.124(4) 0.019(2) 0.053(3) 0.043(3)
N6 0.0699(17) 0.0549(15) 0.0593(15) 0.0258(13) 0.0045(13) 0.0055(12)
C25 0.0619(18) 0.0566(17) 0.0366(13) 0.0188(14) 0.0046(12) 0.0151(12)
C26 0.071(2) 0.0543(17) 0.0446(14) 0.0262(15) 0.0147(13) 0.0174(12)
C31 0.074(2) 0.0528(18) 0.071(2) 0.0186(16) 0.0279(17) 0.0172(15)
C30 0.065(2) 0.071(2) 0.088(3) 0.0138(18) 0.0259(19) 0.024(2)
C29 0.079(2) 0.0532(19) 0.080(2) 0.0059(17) 0.0168(19) 0.0199(17)
C27 0.077(2) 0.063(2) 0.097(3) 0.0332(19) 0.002(2) -0.0019(19)
N7 0.096(3) 0.066(2) 0.135(4) 0.005(2) 0.016(3) 0.018(2)
C28 0.091(3) 0.057(2) 0.104(3) 0.029(2) 0.012(2) -0.001(2)
O5 0.112(3) 0.070(2) 0.144(3) 0.0153(18) -0.024(2) 0.016(2)
_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
C39 O5 . 1.471(7) ?
C39 H39A . 0.9600 ?
C39 H39B . 0.9600 ?
C39 H39C . 0.9600 ?
O1 N7 . 1.195(6) ?
O2 N7 . 1.212(5) ?
Ni1 N5 . 2.056(3) n
Ni1 N8 . 2.062(3) n
Ni1 N4 . 2.076(2) n
Ni1 N1 . 2.097(2) n
Ni1 N3 . 2.098(2) n
Ni1 N2 . 2.139(2) n
N2 C11 . 1.323(3) ?
N2 C12 . 1.358(3) ?
N3 C14 . 1.326(4) ?
N3 C13 . 1.351(4) ?
N1 C2 . 1.325(4) ?
N1 C1 . 1.358(3) ?
N4 C23 . 1.322(4) ?
N4 C24 . 1.352(4) ?
N8 C32 . 1.157(4) n
N5 C25 . 1.156(4) n
C12 C8 . 1.402(4) ?
C12 C1 . 1.435(4) ?
C5 C4 . 1.402(5) ?
C5 C1 . 1.405(4) ?
C5 C6 . 1.433(5) ?
C24 C20 . 1.404(4) ?
C24 C13 . 1.432(4) ?
C13 C17 . 1.407(4) ?
C11 C10 . 1.390(4) ?
C11 H11 . 0.9300 ?
C20 C21 . 1.403(6) ?
C20 C19 . 1.425(6) ?
C6 C7 . 1.342(5) ?
C6 H6 . 0.9300 ?
N9 C32 . 1.297(4) n
N9 C33 . 1.383(3) ?
C38 C37 . 1.378(4) ?
C38 C33 . 1.402(4) ?
C38 H38 . 0.9300 ?
C22 C21 . 1.350(6) ?
C22 C23 . 1.395(4) ?
C22 H22 . 0.9300 ?
C33 C34 . 1.402(4) ?
C8 C9 . 1.401(5) ?
C8 C7 . 1.434(4) ?
C14 C15 . 1.394(6) ?
C14 H14 . 0.9300 ?
C36 C37 . 1.380(4) ?
C36 C35 . 1.383(4) ?
C36 N10 . 1.451(4) ?
C35 C34 . 1.372(4) ?
C35 H35 . 0.9300 ?
C34 H34 . 0.9300 ?
C37 H37 . 0.9300 ?
C23 H23 . 0.9300 ?
C2 C3 . 1.397(4) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.360(5) ?
C3 H3 . 0.9300 ?
C19 C18 . 1.340(6) ?
C19 H19 . 0.9300 ?
C9 C10 . 1.362(5) ?
C9 H9 . 0.9300 ?
C21 H21 . 0.9300 ?
C17 C16 . 1.390(6) ?
C17 C18 . 1.438(6) ?
C10 H10 . 0.9300 ?
O3 N10 . 1.224(4) ?
N10 O4 . 1.215(4) ?
C4 H4 . 0.9300 ?
C7 H7 . 0.9300 ?
C18 H18 . 0.9300 ?
C15 C16 . 1.360(7) ?
C15 H15 . 0.9300 ?
C16 H16 . 0.9300 ?
N6 C25 . 1.289(4) n
N6 C26 . 1.373(4) ?
C26 C31 . 1.388(5) ?
C26 C27 . 1.406(4) ?
C31 C30 . 1.368(5) ?
C31 H31 . 0.9300 ?
C30 C29 . 1.380(5) ?
C30 H30 . 0.9300 ?
C29 C28 . 1.368(6) ?
C29 N7 . 1.451(5) ?
C27 C28 . 1.363(6) ?
C27 H27 . 0.9300 ?
C28 H28 . 0.9300 ?
O5 H5A . 0.91(3) ?
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
O5 C39 H39A . . 109.5 ?
O5 C39 H39B . . 109.5 ?
H39A C39 H39B . . 109.5 ?
O5 C39 H39C . . 109.5 ?
H39A C39 H39C . . 109.5 ?
H39B C39 H39C . . 109.5 ?
N5 Ni1 N8 . . 90.67(12) n
N5 Ni1 N4 . . 94.32(10) n
N8 Ni1 N4 . . 92.39(10) n
N5 Ni1 N1 . . 93.16(10) n
N8 Ni1 N1 . . 89.69(10) n
N4 Ni1 N1 . . 172.22(9) n
N5 Ni1 N3 . . 89.86(11) n
N8 Ni1 N3 . . 171.74(10) n
N4 Ni1 N3 . . 79.35(10) ?
N1 Ni1 N3 . . 98.51(10) ?
N5 Ni1 N2 . . 171.53(9) ?
N8 Ni1 N2 . . 91.08(10) ?
N4 Ni1 N2 . . 93.89(9) ?
N1 Ni1 N2 . . 78.56(9) ?
N3 Ni1 N2 . . 89.59(9) ?
C11 N2 C12 . . 117.8(2) ?
C11 N2 Ni1 . . 129.65(19) ?
C12 N2 Ni1 . . 112.50(17) ?
C14 N3 C13 . . 118.2(3) ?
C14 N3 Ni1 . . 129.1(2) ?
C13 N3 Ni1 . . 112.70(19) ?
C2 N1 C1 . . 118.3(2) ?
C2 N1 Ni1 . . 127.8(2) ?
C1 N1 Ni1 . . 113.33(17) ?
C23 N4 C24 . . 118.1(2) ?
C23 N4 Ni1 . . 128.3(2) ?
C24 N4 Ni1 . . 113.61(18) ?
C32 N8 Ni1 . . 150.6(3) n
C25 N5 Ni1 . . 153.2(2) n
N2 C12 C8 . . 122.8(3) ?
N2 C12 C1 . . 116.9(2) ?
C8 C12 C1 . . 120.2(2) ?
C4 C5 C1 . . 117.4(3) ?
C4 C5 C6 . . 124.0(3) ?
C1 C5 C6 . . 118.6(3) ?
N4 C24 C20 . . 123.0(3) ?
N4 C24 C13 . . 116.9(2) ?
C20 C24 C13 . . 120.1(3) ?
N3 C13 C17 . . 122.9(3) ?
N3 C13 C24 . . 117.4(2) ?
C17 C13 C24 . . 119.7(3) ?
N2 C11 C10 . . 123.1(3) ?
N2 C11 H11 . . 118.5 ?
C10 C11 H11 . . 118.5 ?
C21 C20 C24 . . 116.8(3) ?
C21 C20 C19 . . 124.3(3) ?
C24 C20 C19 . . 118.9(4) ?
C7 C6 C5 . . 121.4(3) ?
C7 C6 H6 . . 119.3 ?
C5 C6 H6 . . 119.3 ?
N1 C1 C5 . . 122.5(3) ?
N1 C1 C12 . . 117.7(2) ?
C5 C1 C12 . . 119.8(3) ?
C32 N9 C33 . . 117.8(2) ?
C37 C38 C33 . . 121.1(3) ?
C37 C38 H38 . . 119.4 ?
C33 C38 H38 . . 119.4 ?
C21 C22 C23 . . 119.7(3) ?
C21 C22 H22 . . 120.2 ?
C23 C22 H22 . . 120.2 ?
N9 C33 C38 . . 123.8(3) ?
N9 C33 C34 . . 118.1(3) ?
C38 C33 C34 . . 118.1(3) ?
C9 C8 C12 . . 117.4(3) ?
C9 C8 C7 . . 124.3(3) ?
C12 C8 C7 . . 118.3(3) ?
N3 C14 C15 . . 122.3(4) ?
N3 C14 H14 . . 118.9 ?
C15 C14 H14 . . 118.9 ?
N8 C32 N9 . . 175.6(3) ?
C37 C36 C35 . . 121.2(3) ?
C37 C36 N10 . . 119.4(3) ?
C35 C36 N10 . . 119.3(3) ?
C34 C35 C36 . . 119.5(3) ?
C34 C35 H35 . . 120.2 ?
C36 C35 H35 . . 120.2 ?
C35 C34 C33 . . 120.9(3) ?
C35 C34 H34 . . 119.6 ?
C33 C34 H34 . . 119.6 ?
C38 C37 C36 . . 119.1(3) ?
C38 C37 H37 . . 120.4 ?
C36 C37 H37 . . 120.4 ?
N4 C23 C22 . . 122.5(3) ?
N4 C23 H23 . . 118.7 ?
C22 C23 H23 . . 118.7 ?
N1 C2 C3 . . 122.6(3) ?
N1 C2 H2 . . 118.7 ?
C3 C2 H2 . . 118.7 ?
C4 C3 C2 . . 119.5(3) ?
C4 C3 H3 . . 120.3 ?
C2 C3 H3 . . 120.3 ?
C18 C19 C20 . . 121.2(3) ?
C18 C19 H19 . . 119.4 ?
C20 C19 H19 . . 119.4 ?
C10 C9 C8 . . 119.4(3) ?
C10 C9 H9 . . 120.3 ?
C8 C9 H9 . . 120.3 ?
C22 C21 C20 . . 119.9(3) ?
C22 C21 H21 . . 120.1 ?
C20 C21 H21 . . 120.1 ?
C16 C17 C13 . . 117.1(4) ?
C16 C17 C18 . . 124.5(4) ?
C13 C17 C18 . . 118.4(4) ?
C9 C10 C11 . . 119.6(3) ?
C9 C10 H10 . . 120.2 ?
C11 C10 H10 . . 120.2 ?
O4 N10 O3 . . 122.2(3) ?
O4 N10 C36 . . 118.9(3) ?
O3 N10 C36 . . 118.9(3) ?
C3 C4 C5 . . 119.6(3) ?
C3 C4 H4 . . 120.2 ?
C5 C4 H4 . . 120.2 ?
C6 C7 C8 . . 121.6(3) ?
C6 C7 H7 . . 119.2 ?
C8 C7 H7 . . 119.2 ?
C19 C18 C17 . . 121.6(3) ?
C19 C18 H18 . . 119.2 ?
C17 C18 H18 . . 119.2 ?
C16 C15 C14 . . 119.6(4) ?
C16 C15 H15 . . 120.2 ?
C14 C15 H15 . . 120.2 ?
C15 C16 C17 . . 119.9(4) ?
C15 C16 H16 . . 120.0 ?
C17 C16 H16 . . 120.0 ?
C25 N6 C26 . . 117.3(3) ?
N5 C25 N6 . . 176.2(4) ?
N6 C26 C31 . . 124.4(3) ?
N6 C26 C27 . . 118.0(3) ?
C31 C26 C27 . . 117.6(3) ?
C30 C31 C26 . . 121.5(3) ?
C30 C31 H31 . . 119.2 ?
C26 C31 H31 . . 119.2 ?
C31 C30 C29 . . 119.3(4) ?
C31 C30 H30 . . 120.3 ?
C29 C30 H30 . . 120.3 ?
C28 C29 C30 . . 120.6(4) ?
C28 C29 N7 . . 120.2(4) ?
C30 C29 N7 . . 119.2(4) ?
C28 C27 C26 . . 120.7(4) ?
C28 C27 H27 . . 119.6 ?
C26 C27 H27 . . 119.6 ?
O1 N7 O2 . . 122.1(5) ?
O1 N7 C29 . . 118.6(5) ?
O2 N7 C29 . . 119.4(4) ?
C27 C28 C29 . . 120.2(3) ?
C27 C28 H28 . . 119.9 ?
C29 C28 H28 . . 119.9 ?
C39 O5 H5A . . 104(4) ?
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
N8 Ni1 N2 C11 . . . . 94.1(3) ?
N4 Ni1 N2 C11 . . . . 1.6(3) ?
N1 Ni1 N2 C11 . . . . -176.5(3) ?
N3 Ni1 N2 C11 . . . . -77.7(3) ?
N8 Ni1 N2 C12 . . . . -82.19(19) ?
N4 Ni1 N2 C12 . . . . -174.66(18) ?
N1 Ni1 N2 C12 . . . . 7.27(18) ?
N3 Ni1 N2 C12 . . . . 106.04(19) ?
N5 Ni1 N3 C14 . . . . 83.3(3) ?
N4 Ni1 N3 C14 . . . . 177.7(3) ?
N1 Ni1 N3 C14 . . . . -9.9(3) ?
N2 Ni1 N3 C14 . . . . -88.2(3) ?
N5 Ni1 N3 C13 . . . . -95.8(2) ?
N4 Ni1 N3 C13 . . . . -1.39(19) ?
N1 Ni1 N3 C13 . . . . 171.02(19) ?
N2 Ni1 N3 C13 . . . . 92.6(2) ?
N5 Ni1 N1 C2 . . . . 2.2(3) ?
N8 Ni1 N1 C2 . . . . -88.5(3) ?
N3 Ni1 N1 C2 . . . . 92.5(3) ?
N2 Ni1 N1 C2 . . . . -179.6(3) ?
N5 Ni1 N1 C1 . . . . 172.90(19) ?
N8 Ni1 N1 C1 . . . . 82.2(2) ?
N3 Ni1 N1 C1 . . . . -96.77(19) ?
N2 Ni1 N1 C1 . . . . -8.92(18) ?
N5 Ni1 N4 C23 . . . . -89.7(3) ?
N8 Ni1 N4 C23 . . . . 1.1(3) ?
N3 Ni1 N4 C23 . . . . -178.8(3) ?
N2 Ni1 N4 C23 . . . . 92.4(3) ?
N5 Ni1 N4 C24 . . . . 90.8(2) ?
N8 Ni1 N4 C24 . . . . -178.4(2) ?
N3 Ni1 N4 C24 . . . . 1.73(18) ?
N2 Ni1 N4 C24 . . . . -87.13(19) ?
N5 Ni1 N8 C32 . . . . -33.3(5) ?
N4 Ni1 N8 C32 . . . . -127.6(5) ?
N1 Ni1 N8 C32 . . . . 59.9(5) ?
N2 Ni1 N8 C32 . . . . 138.4(5) ?
N8 Ni1 N5 C25 . . . . -67.7(6) ?
N4 Ni1 N5 C25 . . . . 24.7(6) ?
N1 Ni1 N5 C25 . . . . -157.5(6) ?
N3 Ni1 N5 C25 . . . . 104.0(6) ?
C11 N2 C12 C8 . . . . -1.1(4) ?
Ni1 N2 C12 C8 . . . . 175.6(2) ?
C11 N2 C12 C1 . . . . 178.6(2) ?
Ni1 N2 C12 C1 . . . . -4.7(3) ?
C23 N4 C24 C20 . . . . -1.0(4) ?
Ni1 N4 C24 C20 . . . . 178.6(2) ?
C23 N4 C24 C13 . . . . 178.6(3) ?
Ni1 N4 C24 C13 . . . . -1.8(3) ?
C14 N3 C13 C17 . . . . 1.2(4) ?
Ni1 N3 C13 C17 . . . . -179.5(2) ?
C14 N3 C13 C24 . . . . -178.3(3) ?
Ni1 N3 C13 C24 . . . . 0.9(3) ?
N4 C24 C13 N3 . . . . 0.6(4) ?
C20 C24 C13 N3 . . . . -179.8(3) ?
N4 C24 C13 C17 . . . . -179.0(3) ?
C20 C24 C13 C17 . . . . 0.6(4) ?
C12 N2 C11 C10 . . . . -0.5(4) ?
Ni1 N2 C11 C10 . . . . -176.6(2) ?
N4 C24 C20 C21 . . . . 1.1(4) ?
C13 C24 C20 C21 . . . . -178.5(3) ?
N4 C24 C20 C19 . . . . 180.0(3) ?
C13 C24 C20 C19 . . . . 0.4(4) ?
C4 C5 C6 C7 . . . . -177.4(4) ?
C1 C5 C6 C7 . . . . 1.8(5) ?
C2 N1 C1 C5 . . . . 0.9(4) ?
Ni1 N1 C1 C5 . . . . -170.8(2) ?
C2 N1 C1 C12 . . . . -178.9(3) ?
Ni1 N1 C1 C12 . . . . 9.5(3) ?
C4 C5 C1 N1 . . . . 0.1(4) ?
C6 C5 C1 N1 . . . . -179.2(3) ?
C4 C5 C1 C12 . . . . 179.8(3) ?
C6 C5 C1 C12 . . . . 0.6(4) ?
N2 C12 C1 N1 . . . . -3.2(4) ?
C8 C12 C1 N1 . . . . 176.5(3) ?
N2 C12 C1 C5 . . . . 177.1(3) ?
C8 C12 C1 C5 . . . . -3.2(4) ?
C32 N9 C33 C38 . . . . 1.2(4) ?
C32 N9 C33 C34 . . . . -178.9(3) ?
C37 C38 C33 N9 . . . . 179.3(3) ?
C37 C38 C33 C34 . . . . -0.6(4) ?
N2 C12 C8 C9 . . . . 2.0(4) ?
C1 C12 C8 C9 . . . . -177.7(3) ?
N2 C12 C8 C7 . . . . -176.8(3) ?
C1 C12 C8 C7 . . . . 3.5(4) ?
C13 N3 C14 C15 . . . . -1.6(5) ?
Ni1 N3 C14 C15 . . . . 179.4(3) ?
C37 C36 C35 C34 . . . . 0.3(5) ?
N10 C36 C35 C34 . . . . -178.1(3) ?
C36 C35 C34 C33 . . . . -0.4(5) ?
N9 C33 C34 C35 . . . . -179.4(3) ?
C38 C33 C34 C35 . . . . 0.5(5) ?
C33 C38 C37 C36 . . . . 0.6(5) ?
C35 C36 C37 C38 . . . . -0.4(5) ?
N10 C36 C37 C38 . . . . 178.0(3) ?
C24 N4 C23 C22 . . . . -0.4(4) ?
Ni1 N4 C23 C22 . . . . -179.9(2) ?
C21 C22 C23 N4 . . . . 1.7(5) ?
C1 N1 C2 C3 . . . . -1.0(5) ?
Ni1 N1 C2 C3 . . . . 169.4(3) ?
N1 C2 C3 C4 . . . . 0.0(5) ?
C21 C20 C19 C18 . . . . 177.8(4) ?
C24 C20 C19 C18 . . . . -1.1(6) ?
C12 C8 C9 C10 . . . . -1.3(5) ?
C7 C8 C9 C10 . . . . 177.4(3) ?
C23 C22 C21 C20 . . . . -1.6(6) ?
C24 C20 C21 C22 . . . . 0.2(5) ?
C19 C20 C21 C22 . . . . -178.6(4) ?
N3 C13 C17 C16 . . . . -0.5(5) ?
C24 C13 C17 C16 . . . . 179.1(3) ?
N3 C13 C17 C18 . . . . 179.4(3) ?
C24 C13 C17 C18 . . . . -1.0(4) ?
C8 C9 C10 C11 . . . . -0.2(5) ?
N2 C11 C10 C9 . . . . 1.2(5) ?
C37 C36 N10 O4 . . . . -2.7(5) ?
C35 C36 N10 O4 . . . . 175.7(3) ?
C37 C36 N10 O3 . . . . 178.6(3) ?
C35 C36 N10 O3 . . . . -2.9(5) ?
C2 C3 C4 C5 . . . . 1.0(5) ?
C1 C5 C4 C3 . . . . -1.0(5) ?
C6 C5 C4 C3 . . . . 178.2(3) ?
C5 C6 C7 C8 . . . . -1.5(6) ?
C9 C8 C7 C6 . . . . -179.9(4) ?
C12 C8 C7 C6 . . . . -1.2(5) ?
C20 C19 C18 C17 . . . . 0.7(6) ?
C16 C17 C18 C19 . . . . -179.8(4) ?
C13 C17 C18 C19 . . . . 0.4(6) ?
N3 C14 C15 C16 . . . . 1.1(6) ?
C14 C15 C16 C17 . . . . -0.3(6) ?
C13 C17 C16 C15 . . . . 0.0(6) ?
C18 C17 C16 C15 . . . . -179.9(4) ?
C26 N6 C25 N5 . . . . 18E1(10)
?
C25 N6 C26 C31 . . . . 6.4(5) ?
C25 N6 C26 C27 . . . . -172.4(3) ?
N6 C26 C31 C30 . . . . -177.7(3) ?
C27 C26 C31 C30 . . . . 1.1(5) ?
C26 C31 C30 C29 . . . . -0.4(5) ?
C31 C30 C29 C28 . . . . -0.2(6) ?
C31 C30 C29 N7 . . . . -178.1(4) ?
N6 C26 C27 C28 . . . . 177.7(4) ?
C31 C26 C27 C28 . . . . -1.2(6) ?
C28 C29 N7 O1 . . . . 7.7(8) ?
C30 C29 N7 O1 . . . . -174.4(6) ?
C28 C29 N7 O2 . . . . -172.6(5) ?
C30 C29 N7 O2 . . . . 5.3(7) ?
C26 C27 C28 C29 . . . . 0.6(7) ?
C30 C29 C28 C27 . . . . 0.1(7) ?
N7 C29 C28 C27 . . . . 178.0(4) ?
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
_geom_hbond_publ_flag
O5 H5A N9 1_455 0.91(3) 1.98(4) 2.883(4) 174(5) y
C39 H39B O4 2_656 0.96 2.55 3.435(7) 152.7 y
C22 H22 O1 2_767 0.93 2.57 3.469(6) 161.9 y
C16 H16 O2 1_445 0.93 2.45 3.312(6) 154.3 y
data_global
_journal_date_recd_electronic 2012-02-05
_journal_date_accepted 2012-03-06
_journal_name_full 'Acta Crystallographica, Section E'
_journal_year 2012
_journal_volume 68
_journal_issue 4
_journal_page_first m417
_journal_page_last m418
_journal_paper_category QM
_journal_paper_doi 10.1107/S1600536812009890
_journal_coeditor_code BT5812
_publ_contact_author_name 'Hossein Chiniforoshan'
_publ_contact_author_address
;
Department of Chemistry
Isfahan University of Technology
Isfahan 84456-38111
Iran
;
_publ_contact_author_email 'chinif@cc.iut.ac.ir'
_publ_contact_author_fax '98(311)3913248'
_publ_contact_author_phone '98(311)3912350'
_publ_section_title
;\
cis-Bis[(4-nitrophenyl)cyanamido-\kN^1^]bis(1,10-phenanthroline-\
\k^2^N,N')nickel(II) methanol monosolvate
;
loop_
_publ_author_name
_publ_author_footnote
_publ_author_address
'Chiniforoshan, Hossein' ?
;
Department of Chemistry
Isfahan University of Technology
Isfahan 84456-38111
Iran
;
'Jazestani, Mehdi' .
;
Department of Chemistry
Isfahan University of Technology
Isfahan 84456-38111
Iran
;
'Notash, Behrouz' .
;
Department of Chemistry, Shahid Beheshti University, G. C.,
Evin, Tehran 1983963113,
Iran
;