##############################################################################
# #
# 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. #
# #
##############################################################################
data_I
_audit_creation_method SHELXL-97
_database_code_depnum_ccdc_archive 'CCDC 1028397'
_chemical_name_systematic
;
3,3'-[(3-Nitrophenyl)methylene]bis(1H-indole-2-carboxylate)
ethanol monosolvate
;
_chemical_name_common ?
_chemical_formula_moiety 'C27 H21 N3 O6, C2 H6 O'
_chemical_formula_sum 'C29 H27 N3 O7'
_chemical_formula_iupac 'C27 H21 N3 O6, C2 H6 O'
_chemical_formula_weight 529.54
_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 11.074(2)
_cell_length_b 11.585(2)
_cell_length_c 12.898(3)
_cell_angle_alpha 114.09(3)
_cell_angle_beta 106.68(3)
_cell_angle_gamma 99.20(3)
_cell_volume 1372.5(5)
_cell_formula_units_Z 2
_cell_measurement_reflns_used 25
_cell_measurement_theta_min 9
_cell_measurement_theta_max 13
_cell_measurement_temperature 293(2)
_exptl_crystal_description block
_exptl_crystal_colour colorless
_exptl_crystal_size_max 0.30
_exptl_crystal_size_mid 0.20
_exptl_crystal_size_min 0.10
_exptl_crystal_density_diffrn 1.281
_exptl_crystal_density_meas ?
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 556
_exptl_absorpt_coefficient_mu 0.093
_exptl_absorpt_correction_type psi-scan
_exptl_absorpt_process_details
;
(North et al., 1968)
;
_exptl_absorpt_correction_T_min 0.9727
_exptl_absorpt_correction_T_max 0.9908
_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 'Enraf--Nonius CAD-4'
_diffrn_measurement_method \w/2\q
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number 5313
_diffrn_reflns_av_R_equivalents 0.0292
_diffrn_reflns_av_sigmaI/netI 0.0487
_diffrn_reflns_theta_min 1.88
_diffrn_reflns_theta_max 25.40
_diffrn_reflns_theta_full 25.40
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_limit_h_min 0
_diffrn_reflns_limit_h_max 13
_diffrn_reflns_limit_k_min -13
_diffrn_reflns_limit_k_max 13
_diffrn_reflns_limit_l_min -15
_diffrn_reflns_limit_l_max 14
_diffrn_standards_number 3
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time .
_diffrn_standards_decay_% 1
_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 5032
_reflns_number_gt 3254
_reflns_threshold_expression I>2sigma(I)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type full
_refine_ls_R_factor_all 0.0998
_refine_ls_R_factor_gt 0.0589
_refine_ls_wR_factor_gt 0.1432
_refine_ls_wR_factor_ref 0.1655
_refine_ls_goodness_of_fit_ref 1.042
_refine_ls_restrained_S_all 1.042
_refine_ls_number_reflns 5032
_refine_ls_number_parameters 352
_refine_ls_number_restraints 0
_refine_ls_hydrogen_treatment constr
_refine_ls_weighting_scheme calc
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0769P)^2^+0.4188P] 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 0.186
_refine_diff_density_min -0.255
_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'
_computing_data_collection
;
CAD4 EXPRESS (Enraf--Nonius, 1994)
;
_computing_cell_refinement
;
CAD4 EXPRESS (Enraf--Nonius, 1994)
;
_computing_data_reduction
;
XCAD4 (Harms & Wocadlo, 1995)
;
_computing_structure_solution
;
SHELXTL (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXTL (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
N N1 0.4712(3) -0.2518(3) 0.0074(4) 0.0901(11) Uani d . 1 1 . .
N N2 1.1545(2) 0.0075(2) 0.4249(2) 0.0438(6) Uani d . 1 1 . .
H H2A 1.2151 0.0123 0.4870 0.053 Uiso calc R 1 1 . .
N N3 0.9859(2) 0.4742(2) 0.3448(2) 0.0414(5) Uani d . 1 1 . .
H H3A 0.9740 0.5507 0.3650 0.050 Uiso calc R 1 1 . .
O O1 0.4711(3) -0.2634(3) 0.0977(4) 0.1266(13) Uani d . 1 1 . .
O O2 0.3872(3) -0.3273(3) -0.0959(3) 0.1360(14) Uani d . 1 1 . .
O O3 1.1911(2) 0.21184(19) 0.64357(18) 0.0599(6) Uani d . 1 1 . .
O O4 1.0053(2) 0.25277(18) 0.55999(17) 0.0506(5) Uani d . 1 1 . .
O O5 0.71167(19) 0.2865(2) 0.36509(19) 0.0548(5) Uani d . 1 1 . .
O O6 0.77081(18) 0.49394(18) 0.39092(18) 0.0504(5) Uani d . 1 1 . .
O O7 0.6624(2) 0.0902(2) 0.4450(2) 0.0733(7) Uani d . 1 1 . .
H H7B 0.7018 0.1489 0.4354 0.110 Uiso calc R 1 1 . .
C C1 0.6788(3) -0.0661(3) 0.1405(3) 0.0490(7) Uani d . 1 1 . .
H H1A 0.6817 -0.0846 0.2047 0.059 Uiso calc R 1 1 . .
C C2 0.5754(3) -0.1429(3) 0.0248(3) 0.0565(8) Uani d . 1 1 . .
C C3 0.5662(3) -0.1189(3) -0.0723(3) 0.0616(9) Uani d . 1 1 . .
H H3B 0.4956 -0.1715 -0.1484 0.074 Uiso calc R 1 1 . .
C C4 0.6637(3) -0.0153(3) -0.0543(3) 0.0607(9) Uani d . 1 1 . .
H H4A 0.6603 0.0025 -0.1190 0.073 Uiso calc R 1 1 . .
C C5 0.7674(3) 0.0629(3) 0.0598(3) 0.0497(7) Uani d . 1 1 . .
H H5A 0.8323 0.1337 0.0710 0.060 Uiso calc R 1 1 . .
C C6 0.7767(3) 0.0382(2) 0.1580(2) 0.0395(6) Uani d . 1 1 . .
C C7 0.8906(2) 0.1240(2) 0.2847(2) 0.0361(6) Uani d . 1 1 . .
H H7A 0.8495 0.1390 0.3451 0.043 Uiso calc R 1 1 . .
C C8 0.9896(2) 0.0532(2) 0.3134(2) 0.0354(6) Uani d . 1 1 . .
C C9 1.0194(3) -0.0546(2) 0.2304(2) 0.0389(6) Uani d . 1 1 . .
C C10 0.9715(3) -0.1346(3) 0.1015(3) 0.0484(7) Uani d . 1 1 . .
H H10A 0.9044 -0.1207 0.0497 0.058 Uiso calc R 1 1 . .
C C11 1.0243(3) -0.2330(3) 0.0530(3) 0.0598(8) Uani d . 1 1 . .
H H11A 0.9910 -0.2870 -0.0321 0.072 Uiso calc R 1 1 . .
C C12 1.1276(3) -0.2544(3) 0.1288(3) 0.0609(9) Uani d . 1 1 . .
H H12A 1.1624 -0.3211 0.0930 0.073 Uiso calc R 1 1 . .
C C13 1.1778(3) -0.1789(3) 0.2542(3) 0.0524(8) Uani d . 1 1 . .
H H13A 1.2462 -0.1931 0.3044 0.063 Uiso calc R 1 1 . .
C C14 1.1231(3) -0.0798(3) 0.3043(2) 0.0410(6) Uani d . 1 1 . .
C C15 1.0733(3) 0.0872(2) 0.4314(2) 0.0390(6) Uani d . 1 1 . .
C C16 1.0840(3) 0.1913(3) 0.5490(2) 0.0425(7) Uani d . 1 1 . .
C C17 1.2112(4) 0.3165(3) 0.7644(3) 0.0695(10) Uani d . 1 1 . .
H H17A 1.2900 0.3234 0.8255 0.104 Uiso calc R 1 1 . .
H H17B 1.1360 0.2952 0.7838 0.104 Uiso calc R 1 1 . .
H H17C 1.2208 0.3999 0.7635 0.104 Uiso calc R 1 1 . .
C C18 0.9553(2) 0.2606(2) 0.3046(2) 0.0359(6) Uani d . 1 1 . .
C C19 1.0709(3) 0.3062(2) 0.2854(2) 0.0378(6) Uani d . 1 1 . .
C C20 1.1640(3) 0.2491(3) 0.2473(3) 0.0477(7) Uani d . 1 1 . .
H H20A 1.1577 0.1615 0.2292 0.057 Uiso calc R 1 1 . .
C C21 1.2643(3) 0.3253(3) 0.2377(3) 0.0624(9) Uani d . 1 1 . .
H H21A 1.3258 0.2880 0.2123 0.075 Uiso calc R 1 1 . .
C C22 1.2763(3) 0.4570(3) 0.2648(3) 0.0631(9) Uani d . 1 1 . .
H H22A 1.3456 0.5054 0.2570 0.076 Uiso calc R 1 1 . .
C C23 1.1893(3) 0.5166(3) 0.3023(3) 0.0529(8) Uani d . 1 1 . .
H H23A 1.1980 0.6047 0.3208 0.064 Uiso calc R 1 1 . .
C C24 1.0863(3) 0.4401(3) 0.3120(2) 0.0399(6) Uani d . 1 1 . .
C C25 0.9066(2) 0.3671(2) 0.3405(2) 0.0366(6) Uani d . 1 1 . .
C C26 0.7876(3) 0.3752(3) 0.3664(2) 0.0394(6) Uani d . 1 1 . .
C C27 0.6529(3) 0.5128(3) 0.4122(3) 0.0663(9) Uani d . 1 1 . .
H H27A 0.6516 0.6011 0.4285 0.099 Uiso calc R 1 1 . .
H H27B 0.6530 0.5013 0.4819 0.099 Uiso calc R 1 1 . .
H H27C 0.5757 0.4485 0.3405 0.099 Uiso calc R 1 1 . .
C C28 0.5250(4) 0.0591(4) 0.3849(4) 0.0870(12) Uani d . 1 1 . .
H H28A 0.4800 -0.0202 0.3845 0.104 Uiso calc R 1 1 . .
H H28B 0.5049 0.0384 0.2998 0.104 Uiso calc R 1 1 . .
C C29 0.4715(4) 0.1671(5) 0.4421(5) 0.1096(17) Uani d . 1 1 . .
H H29A 0.3772 0.1388 0.3969 0.164 Uiso calc R 1 1 . .
H H29B 0.5131 0.2452 0.4404 0.164 Uiso calc R 1 1 . .
H H29C 0.4894 0.1872 0.5260 0.164 Uiso calc R 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
N1 0.062(2) 0.059(2) 0.101(3) -0.0028(16) 0.000(2) 0.025(2)
N2 0.0404(13) 0.0425(13) 0.0432(14) 0.0130(11) 0.0046(10) 0.0235(11)
N3 0.0425(13) 0.0313(11) 0.0503(14) 0.0153(10) 0.0173(11) 0.0187(10)
O1 0.096(2) 0.107(3) 0.129(3) -0.0288(19) 0.014(2) 0.057(2)
O2 0.102(2) 0.087(2) 0.109(3) -0.0398(19) -0.024(2) 0.0179(19)
O3 0.0643(14) 0.0489(12) 0.0396(12) 0.0150(10) -0.0031(10) 0.0140(10)
O4 0.0582(13) 0.0395(11) 0.0457(12) 0.0168(10) 0.0147(10) 0.0163(9)
O5 0.0454(12) 0.0523(12) 0.0729(15) 0.0170(10) 0.0255(11) 0.0333(11)
O6 0.0448(11) 0.0443(11) 0.0645(13) 0.0227(9) 0.0227(10) 0.0243(10)
O7 0.0597(14) 0.0859(17) 0.0859(17) 0.0228(13) 0.0164(13) 0.0598(15)
C1 0.0440(16) 0.0369(15) 0.0531(18) 0.0118(13) 0.0097(14) 0.0166(13)
C2 0.0388(16) 0.0382(16) 0.064(2) 0.0084(13) 0.0055(15) 0.0110(15)
C3 0.0479(19) 0.054(2) 0.0476(19) 0.0224(16) -0.0033(15) 0.0054(15)
C4 0.060(2) 0.065(2) 0.0404(17) 0.0271(18) 0.0054(15) 0.0173(15)
C5 0.0463(17) 0.0507(17) 0.0430(17) 0.0149(14) 0.0090(14) 0.0203(14)
C6 0.0372(14) 0.0332(14) 0.0385(15) 0.0163(12) 0.0081(12) 0.0114(12)
C7 0.0359(14) 0.0326(13) 0.0357(14) 0.0115(11) 0.0112(11) 0.0142(11)
C8 0.0331(14) 0.0305(13) 0.0385(15) 0.0076(11) 0.0090(11) 0.0171(11)
C9 0.0396(15) 0.0355(14) 0.0413(15) 0.0124(12) 0.0117(12) 0.0207(12)
C10 0.0544(18) 0.0459(16) 0.0425(17) 0.0196(14) 0.0143(14) 0.0208(14)
C11 0.077(2) 0.0561(19) 0.0492(18) 0.0301(18) 0.0282(17) 0.0225(15)
C12 0.073(2) 0.0516(18) 0.071(2) 0.0364(17) 0.0347(19) 0.0298(17)
C13 0.0521(18) 0.0464(17) 0.063(2) 0.0234(14) 0.0187(16) 0.0296(16)
C14 0.0419(15) 0.0367(14) 0.0438(16) 0.0112(12) 0.0134(13) 0.0215(13)
C15 0.0394(15) 0.0315(13) 0.0419(15) 0.0086(12) 0.0096(12) 0.0189(12)
C16 0.0462(16) 0.0325(14) 0.0395(16) 0.0052(13) 0.0062(13) 0.0185(12)
C17 0.086(3) 0.0516(19) 0.0377(18) 0.0107(18) -0.0004(17) 0.0122(15)
C18 0.0348(14) 0.0337(13) 0.0319(14) 0.0104(11) 0.0062(11) 0.0141(11)
C19 0.0365(14) 0.0350(14) 0.0348(14) 0.0113(12) 0.0090(12) 0.0139(12)
C20 0.0458(17) 0.0403(15) 0.0557(18) 0.0156(13) 0.0210(14) 0.0205(14)
C21 0.053(2) 0.063(2) 0.074(2) 0.0243(17) 0.0356(18) 0.0269(18)
C22 0.0520(19) 0.056(2) 0.083(2) 0.0128(16) 0.0345(18) 0.0313(18)
C23 0.0534(18) 0.0423(16) 0.065(2) 0.0129(15) 0.0245(16) 0.0278(15)
C24 0.0390(15) 0.0374(14) 0.0397(15) 0.0115(12) 0.0118(12) 0.0179(12)
C25 0.0358(14) 0.0320(13) 0.0357(14) 0.0108(11) 0.0088(11) 0.0141(11)
C26 0.0351(14) 0.0378(15) 0.0394(15) 0.0115(12) 0.0085(12) 0.0174(12)
C27 0.0509(19) 0.071(2) 0.085(3) 0.0347(17) 0.0318(18) 0.035(2)
C28 0.062(2) 0.098(3) 0.091(3) 0.010(2) 0.005(2) 0.059(3)
C29 0.070(3) 0.117(4) 0.187(5) 0.039(3) 0.061(3) 0.103(4)
_geom_special_details
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds 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
N1 O2 . 1.218(4) ?
N1 O1 . 1.226(5) ?
N1 C2 . 1.459(5) ?
N2 C14 . 1.362(3) ?
N2 C15 . 1.383(3) ?
N2 H2A . 0.8600 ?
N3 C24 . 1.358(3) ?
N3 C25 . 1.372(3) ?
N3 H3A . 0.8600 ?
O3 C16 . 1.339(3) ?
O3 C17 . 1.456(4) ?
O4 C16 . 1.214(3) ?
O5 C26 . 1.211(3) ?
O6 C26 . 1.337(3) ?
O6 C27 . 1.441(3) ?
O7 C28 . 1.402(4) ?
O7 H7B . 0.8200 ?
C1 C6 . 1.380(4) ?
C1 C2 . 1.393(4) ?
C1 H1A . 0.9300 ?
C2 C3 . 1.370(5) ?
C3 C4 . 1.369(5) ?
C3 H3B . 0.9300 ?
C4 C5 . 1.384(4) ?
C4 H4A . 0.9300 ?
C5 C6 . 1.388(4) ?
C5 H5A . 0.9300 ?
C6 C7 . 1.529(4) ?
C7 C18 . 1.511(3) ?
C7 C8 . 1.521(3) ?
C7 H7A . 0.9800 ?
C8 C15 . 1.384(3) ?
C8 C9 . 1.435(4) ?
C9 C10 . 1.408(4) ?
C9 C14 . 1.420(4) ?
C10 C11 . 1.369(4) ?
C10 H10A . 0.9300 ?
C11 C12 . 1.404(4) ?
C11 H11A . 0.9300 ?
C12 C13 . 1.364(4) ?
C12 H12A . 0.9300 ?
C13 C14 . 1.395(4) ?
C13 H13A . 0.9300 ?
C15 C16 . 1.458(4) ?
C17 H17A . 0.9600 ?
C17 H17B . 0.9600 ?
C17 H17C . 0.9600 ?
C18 C25 . 1.385(3) ?
C18 C19 . 1.433(4) ?
C19 C20 . 1.409(4) ?
C19 C24 . 1.414(4) ?
C20 C21 . 1.372(4) ?
C20 H20A . 0.9300 ?
C21 C22 . 1.393(4) ?
C21 H21A . 0.9300 ?
C22 C23 . 1.359(4) ?
C22 H22A . 0.9300 ?
C23 C24 . 1.397(4) ?
C23 H23A . 0.9300 ?
C25 C26 . 1.457(4) ?
C27 H27A . 0.9600 ?
C27 H27B . 0.9600 ?
C27 H27C . 0.9600 ?
C28 C29 . 1.482(6) ?
C28 H28A . 0.9700 ?
C28 H28B . 0.9700 ?
C29 H29A . 0.9600 ?
C29 H29B . 0.9600 ?
C29 H29C . 0.9600 ?
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
O2 N1 O1 . . 122.4(4) ?
O2 N1 C2 . . 118.9(4) ?
O1 N1 C2 . . 118.7(3) ?
C14 N2 C15 . . 109.2(2) ?
C14 N2 H2A . . 125.4 ?
C15 N2 H2A . . 125.4 ?
C24 N3 C25 . . 109.1(2) ?
C24 N3 H3A . . 125.4 ?
C25 N3 H3A . . 125.4 ?
C16 O3 C17 . . 115.9(2) ?
C26 O6 C27 . . 117.0(2) ?
C28 O7 H7B . . 109.5 ?
C6 C1 C2 . . 118.6(3) ?
C6 C1 H1A . . 120.7 ?
C2 C1 H1A . . 120.7 ?
C3 C2 C1 . . 122.8(3) ?
C3 C2 N1 . . 118.8(3) ?
C1 C2 N1 . . 118.3(3) ?
C4 C3 C2 . . 118.2(3) ?
C4 C3 H3B . . 120.9 ?
C2 C3 H3B . . 120.9 ?
C3 C4 C5 . . 120.2(3) ?
C3 C4 H4A . . 119.9 ?
C5 C4 H4A . . 119.9 ?
C4 C5 C6 . . 121.5(3) ?
C4 C5 H5A . . 119.2 ?
C6 C5 H5A . . 119.2 ?
C1 C6 C5 . . 118.6(3) ?
C1 C6 C7 . . 119.3(2) ?
C5 C6 C7 . . 122.1(2) ?
C18 C7 C8 . . 113.3(2) ?
C18 C7 C6 . . 112.2(2) ?
C8 C7 C6 . . 113.1(2) ?
C18 C7 H7A . . 105.8 ?
C8 C7 H7A . . 105.8 ?
C6 C7 H7A . . 105.8 ?
C15 C8 C9 . . 106.5(2) ?
C15 C8 C7 . . 124.1(2) ?
C9 C8 C7 . . 129.4(2) ?
C10 C9 C14 . . 117.5(2) ?
C10 C9 C8 . . 135.7(2) ?
C14 C9 C8 . . 106.8(2) ?
C11 C10 C9 . . 119.5(3) ?
C11 C10 H10A . . 120.3 ?
C9 C10 H10A . . 120.3 ?
C10 C11 C12 . . 121.5(3) ?
C10 C11 H11A . . 119.2 ?
C12 C11 H11A . . 119.2 ?
C13 C12 C11 . . 121.1(3) ?
C13 C12 H12A . . 119.4 ?
C11 C12 H12A . . 119.4 ?
C12 C13 C14 . . 117.7(3) ?
C12 C13 H13A . . 121.2 ?
C14 C13 H13A . . 121.2 ?
N2 C14 C13 . . 129.2(3) ?
N2 C14 C9 . . 108.1(2) ?
C13 C14 C9 . . 122.7(3) ?
N2 C15 C8 . . 109.5(2) ?
N2 C15 C16 . . 121.9(2) ?
C8 C15 C16 . . 128.6(2) ?
O4 C16 O3 . . 123.8(3) ?
O4 C16 C15 . . 123.9(2) ?
O3 C16 C15 . . 112.2(2) ?
O3 C17 H17A . . 109.5 ?
O3 C17 H17B . . 109.5 ?
H17A C17 H17B . . 109.5 ?
O3 C17 H17C . . 109.5 ?
H17A C17 H17C . . 109.5 ?
H17B C17 H17C . . 109.5 ?
C25 C18 C19 . . 105.9(2) ?
C25 C18 C7 . . 124.8(2) ?
C19 C18 C7 . . 129.2(2) ?
C20 C19 C24 . . 117.8(2) ?
C20 C19 C18 . . 135.2(2) ?
C24 C19 C18 . . 107.0(2) ?
C21 C20 C19 . . 118.7(3) ?
C21 C20 H20A . . 120.6 ?
C19 C20 H20A . . 120.6 ?
C20 C21 C22 . . 121.8(3) ?
C20 C21 H21A . . 119.1 ?
C22 C21 H21A . . 119.1 ?
C23 C22 C21 . . 121.6(3) ?
C23 C22 H22A . . 119.2 ?
C21 C22 H22A . . 119.2 ?
C22 C23 C24 . . 117.3(3) ?
C22 C23 H23A . . 121.4 ?
C24 C23 H23A . . 121.4 ?
N3 C24 C23 . . 129.1(2) ?
N3 C24 C19 . . 108.2(2) ?
C23 C24 C19 . . 122.8(3) ?
N3 C25 C18 . . 109.9(2) ?
N3 C25 C26 . . 120.3(2) ?
C18 C25 C26 . . 129.7(2) ?
O5 C26 O6 . . 123.4(2) ?
O5 C26 C25 . . 125.2(2) ?
O6 C26 C25 . . 111.4(2) ?
O6 C27 H27A . . 109.5 ?
O6 C27 H27B . . 109.5 ?
H27A C27 H27B . . 109.5 ?
O6 C27 H27C . . 109.5 ?
H27A C27 H27C . . 109.5 ?
H27B C27 H27C . . 109.5 ?
O7 C28 C29 . . 114.0(4) ?
O7 C28 H28A . . 108.8 ?
C29 C28 H28A . . 108.8 ?
O7 C28 H28B . . 108.8 ?
C29 C28 H28B . . 108.8 ?
H28A C28 H28B . . 107.7 ?
C28 C29 H29A . . 109.5 ?
C28 C29 H29B . . 109.5 ?
H29A C29 H29B . . 109.5 ?
C28 C29 H29C . . 109.5 ?
H29A C29 H29C . . 109.5 ?
H29B C29 H29C . . 109.5 ?
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
C6 C1 C2 C3 . . . . -0.5(4) ?
C6 C1 C2 N1 . . . . -179.1(3) ?
O2 N1 C2 C3 . . . . 8.1(5) ?
O1 N1 C2 C3 . . . . -171.5(4) ?
O2 N1 C2 C1 . . . . -173.3(3) ?
O1 N1 C2 C1 . . . . 7.1(5) ?
C1 C2 C3 C4 . . . . 0.6(5) ?
N1 C2 C3 C4 . . . . 179.1(3) ?
C2 C3 C4 C5 . . . . -0.7(5) ?
C3 C4 C5 C6 . . . . 0.9(5) ?
C2 C1 C6 C5 . . . . 0.6(4) ?
C2 C1 C6 C7 . . . . 179.7(2) ?
C4 C5 C6 C1 . . . . -0.8(4) ?
C4 C5 C6 C7 . . . . -179.9(2) ?
C1 C6 C7 C18 . . . . -157.0(2) ?
C5 C6 C7 C18 . . . . 22.1(3) ?
C1 C6 C7 C8 . . . . 73.4(3) ?
C5 C6 C7 C8 . . . . -107.6(3) ?
C18 C7 C8 C15 . . . . 73.3(3) ?
C6 C7 C8 C15 . . . . -157.5(2) ?
C18 C7 C8 C9 . . . . -104.8(3) ?
C6 C7 C8 C9 . . . . 24.3(4) ?
C15 C8 C9 C10 . . . . 179.2(3) ?
C7 C8 C9 C10 . . . . -2.4(5) ?
C15 C8 C9 C14 . . . . -0.7(3) ?
C7 C8 C9 C14 . . . . 177.7(2) ?
C14 C9 C10 C11 . . . . 0.8(4) ?
C8 C9 C10 C11 . . . . -179.1(3) ?
C9 C10 C11 C12 . . . . -1.4(5) ?
C10 C11 C12 C13 . . . . 1.1(5) ?
C11 C12 C13 C14 . . . . -0.1(5) ?
C15 N2 C14 C13 . . . . -179.4(3) ?
C15 N2 C14 C9 . . . . 0.8(3) ?
C12 C13 C14 N2 . . . . 179.7(3) ?
C12 C13 C14 C9 . . . . -0.5(4) ?
C10 C9 C14 N2 . . . . -180.0(2) ?
C8 C9 C14 N2 . . . . -0.1(3) ?
C10 C9 C14 C13 . . . . 0.2(4) ?
C8 C9 C14 C13 . . . . -179.9(3) ?
C14 N2 C15 C8 . . . . -1.2(3) ?
C14 N2 C15 C16 . . . . -179.7(2) ?
C9 C8 C15 N2 . . . . 1.2(3) ?
C7 C8 C15 N2 . . . . -177.3(2) ?
C9 C8 C15 C16 . . . . 179.5(3) ?
C7 C8 C15 C16 . . . . 1.0(4) ?
C17 O3 C16 O4 . . . . -1.0(4) ?
C17 O3 C16 C15 . . . . 178.6(2) ?
N2 C15 C16 O4 . . . . -171.1(2) ?
C8 C15 C16 O4 . . . . 10.7(4) ?
N2 C15 C16 O3 . . . . 9.3(4) ?
C8 C15 C16 O3 . . . . -168.9(3) ?
C8 C7 C18 C25 . . . . -149.2(2) ?
C6 C7 C18 C25 . . . . 81.3(3) ?
C8 C7 C18 C19 . . . . 34.6(4) ?
C6 C7 C18 C19 . . . . -95.0(3) ?
C25 C18 C19 C20 . . . . -178.9(3) ?
C7 C18 C19 C20 . . . . -2.1(5) ?
C25 C18 C19 C24 . . . . 0.5(3) ?
C7 C18 C19 C24 . . . . 177.3(2) ?
C24 C19 C20 C21 . . . . -0.2(4) ?
C18 C19 C20 C21 . . . . 179.1(3) ?
C19 C20 C21 C22 . . . . 0.2(5) ?
C20 C21 C22 C23 . . . . 0.0(5) ?
C21 C22 C23 C24 . . . . -0.4(5) ?
C25 N3 C24 C23 . . . . 179.3(3) ?
C25 N3 C24 C19 . . . . 0.2(3) ?
C22 C23 C24 N3 . . . . -178.7(3) ?
C22 C23 C24 C19 . . . . 0.4(4) ?
C20 C19 C24 N3 . . . . 179.1(2) ?
C18 C19 C24 N3 . . . . -0.4(3) ?
C20 C19 C24 C23 . . . . -0.1(4) ?
C18 C19 C24 C23 . . . . -179.6(3) ?
C24 N3 C25 C18 . . . . 0.1(3) ?
C24 N3 C25 C26 . . . . -177.3(2) ?
C19 C18 C25 N3 . . . . -0.4(3) ?
C7 C18 C25 N3 . . . . -177.4(2) ?
C19 C18 C25 C26 . . . . 176.8(2) ?
C7 C18 C25 C26 . . . . -0.2(4) ?
C27 O6 C26 O5 . . . . -2.3(4) ?
C27 O6 C26 C25 . . . . 177.0(2) ?
N3 C25 C26 O5 . . . . -179.9(2) ?
C18 C25 C26 O5 . . . . 3.2(4) ?
N3 C25 C26 O6 . . . . 0.8(3) ?
C18 C25 C26 O6 . . . . -176.1(2) ?
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
N2 H2A O7 2_756 0.86 2.17 2.924(3) 146
N3 H3A O4 2_766 0.86 2.02 2.861(4) 166
O7 H7B O5 . 0.82 2.13 2.892(4) 154
C10 H10A Cg3 1_555 0.93 2.87 3.633(4) 140
C11 H11A Cg5 2_755 0.93 2.76 3.634(4) 156
C17 H17B Cg4 2_756 0.96 2.89 3.813(5) 163
C27 H27B Cg5 2_766 0.96 2.75 3.496(4) 135
data_global
_journal_date_recd_electronic 2014-09-25
_journal_date_accepted 2014-10-09
_journal_name_full 'Acta Crystallographica, Section E'
_journal_year 2014
_journal_volume 70
_journal_issue 11
_journal_page_first 370
_journal_page_last 372
_journal_paper_category GO
_journal_paper_doi 10.1107/S1600536814022296
_journal_coeditor_code XU5823
_publ_contact_author_name 'Sun, Hong-shun'
_publ_contact_author_address
;
Chemical Engineering Department
Nanjing College of Chemical Technology
Geguan Road No.265 Nanjing
Nanjing 210048
People's Republic of China
;
_publ_contact_author_email
;
njutshs@126.com
;
_publ_contact_author_fax '86 25 58370621'
_publ_contact_author_phone '86 25 58370534'
_publ_section_title
;
Crystal structure of dimethyl
3,3'-[(3-nitrophenyl)methylene]bis(1H-indole-2-carboxylate) ethanol
monosolvate
;
loop_
_publ_author_name
_publ_author_address
'Sun, Hong-Shun'
;
Chemical Engineering Department
Nanjing College of Chemical Technology
Nanjing 210048
People's Republic of China
;
'Li, Yu-Long'
;
Chemical Engineering Department
Nanjing College of Chemical Technology
Nanjing 210048
People's Republic of China
;
'Jiang, Hong'
;
Chemical Engineering Department
Nanjing College of Chemical Technology
Nanjing 210048
People's Republic of China
;
'Xu, Ning'
;
Chemical Engineering Department
Nanjing College of Chemical Technology
Nanjing 210048
People's Republic of China
;
'Xu, Hong'
;
Chemical Engineering Department
Nanjing College of Chemical Technology
Nanjing 210048
People's Republic of China
;
_publ_section_synopsis
;
In the title compound, the planes of the two indole ring systems are
approximately perpendicular to each other, with a dihedral angle of 89.3(5)\%.
;