#------------------------------------------------------------------------------ #$Date: 2013-08-29 16:37:19 +0100 (Thu, 29 Aug 2013) $ #$Revision: 88064 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/66/2206656.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided by IUCr Journals, http://journals.iucr.org/. # # The file may be used within the scientific community so long as # proper attribution is given to the journal article from which the # data were obtained. # data_2206656 loop_ _publ_author_name 'Chen, Lian-Qing' 'Yang, Chu-Luo' 'Meng, Xiang-Gao' 'Qin, Jin-Gui' _publ_section_title ; 9-(4-Nitrophenyl)-9H-carbazole ; _journal_coeditor_code CI6626 _journal_issue 9 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o3073 _journal_page_last o3075 _journal_volume 61 _journal_year 2005 _chemical_formula_iupac 'C18 H12 N2 O2' _chemical_formula_moiety 'C18 H12 N2 O2' _chemical_formula_sum 'C18 H12 N2 O2' _chemical_formula_weight 288.30 _chemical_name_systematic ; 9-(4-Nitrophenyl)-9H-carbazole ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL97 _cell_angle_alpha 90.00 _cell_angle_beta 105.592(4) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 8.356(2) _cell_length_b 21.620(5) _cell_length_c 8.153(2) _cell_measurement_reflns_used 2691 _cell_measurement_temperature 292(2) _cell_measurement_theta_max 25.55 _cell_measurement_theta_min 2.22 _cell_volume 1418.7(6) _computing_cell_refinement 'SAINT (Siemens, 1996)' _computing_data_collection 'SMART (Siemens, 1996)' _computing_data_reduction SAINT _computing_molecular_graphics 'SHELXTL (Sheldrick, 1997b)' _computing_publication_material SHELXTL _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997a)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997a)' _diffrn_ambient_temperature 292(2) _diffrn_measured_fraction_theta_full 0.992 _diffrn_measured_fraction_theta_max 0.992 _diffrn_measurement_device_type 'Siemens SMART CCD area-detector' _diffrn_measurement_method '\f and \w' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0476 _diffrn_reflns_av_sigmaI/netI 0.0384 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_k_min -25 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_number 9337 _diffrn_reflns_theta_full 26.99 _diffrn_reflns_theta_max 26.99 _diffrn_reflns_theta_min 1.88 _diffrn_standards_decay_% 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.090 _exptl_absorpt_correction_T_max 0.9858 _exptl_absorpt_correction_T_min 0.9701 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)' _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.350 _exptl_crystal_density_method 'not measured' _exptl_crystal_description Block _exptl_crystal_F_000 600 _exptl_crystal_size_max 0.34 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.16 _refine_diff_density_max 0.149 _refine_diff_density_min -0.215 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.964 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 199 _refine_ls_number_reflns 3079 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.964 _refine_ls_R_factor_all 0.0646 _refine_ls_R_factor_gt 0.0453 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0659P)^2^] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1107 _refine_ls_wR_factor_ref 0.1196 _reflns_number_gt 2132 _reflns_number_total 3079 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file ci6626.cif _[local]_cod_data_source_block I _[local]_cod_cif_authors_sg_H-M 'P 21/c' _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic' according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius The following automatic conversions were performed: '_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana ; _cod_database_code 2206656 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' loop_ _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_type_symbol C1 0.39653(18) 0.64622(6) -0.16802(17) 0.0464(3) Uani d . 1 C C2 0.22878(19) 0.64441(7) -0.25192(19) 0.0537(4) Uani d . 1 C H2 0.1541 0.6221 -0.2086 0.064 Uiso calc R 1 H C3 0.1772(2) 0.67695(8) -0.4020(2) 0.0644(4) Uani d . 1 C H3 0.0651 0.6768 -0.4606 0.077 Uiso calc R 1 H C4 0.2880(2) 0.71000(7) -0.4682(2) 0.0683(5) Uani d . 1 C H4 0.2491 0.7311 -0.5707 0.082 Uiso calc R 1 H C5 0.4545(2) 0.71203(7) -0.3844(2) 0.0624(4) Uani d . 1 C H5 0.5280 0.7345 -0.4290 0.075 Uiso calc R 1 H C6 0.51101(18) 0.67991(6) -0.23173(18) 0.0502(4) Uani d . 1 C C7 0.67232(18) 0.67304(6) -0.11069(19) 0.0507(4) Uani d . 1 C C8 0.8315(2) 0.69328(8) -0.1071(2) 0.0666(5) Uani d . 1 C H8 0.8491 0.7178 -0.1944 0.080 Uiso calc R 1 H C9 0.9617(2) 0.67644(9) 0.0273(3) 0.0740(5) Uani d . 1 C H9 1.0684 0.6897 0.0306 0.089 Uiso calc R 1 H C10 0.9373(2) 0.63998(8) 0.1587(2) 0.0675(5) Uani d . 1 C H10 1.0281 0.6290 0.2479 0.081 Uiso calc R 1 H C11 0.78152(19) 0.61972(7) 0.1596(2) 0.0566(4) Uani d . 1 C H11 0.7654 0.5955 0.2480 0.068 Uiso calc R 1 H C12 0.64945(17) 0.63676(6) 0.02394(18) 0.0467(4) Uani d . 1 C C13 0.40942(16) 0.58546(6) 0.09815(17) 0.0446(3) Uani d . 1 C C14 0.44030(18) 0.60276(6) 0.26771(18) 0.0500(4) Uani d . 1 C H14 0.5053 0.6374 0.3075 0.060 Uiso calc R 1 H C15 0.37477(17) 0.56880(7) 0.37736(18) 0.0510(4) Uani d . 1 C H15 0.3959 0.5798 0.4915 0.061 Uiso calc R 1 H C16 0.27737(17) 0.51822(6) 0.31454(18) 0.0492(4) Uani d . 1 C C17 0.24367(18) 0.50062(7) 0.14707(19) 0.0554(4) Uani d . 1 C H17 0.1769 0.4664 0.1078 0.066 Uiso calc R 1 H C18 0.31024(17) 0.53444(7) 0.03781(18) 0.0525(4) Uani d . 1 C H18 0.2887 0.5231 -0.0761 0.063 Uiso calc R 1 H N1 0.48130(14) 0.62002(5) -0.01172(14) 0.0477(3) Uani d . 1 N N2 0.20891(17) 0.48228(7) 0.43288(19) 0.0658(4) Uani d . 1 N O1 0.1357(2) 0.43467(7) 0.3819(2) 0.1154(6) Uani d . 1 O O2 0.23075(18) 0.50086(6) 0.57704(18) 0.0925(4) Uani d . 1 O 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 C1 0.0574(9) 0.0428(8) 0.0424(8) 0.0027(6) 0.0193(7) -0.0021(6) C2 0.0583(10) 0.0559(9) 0.0489(9) 0.0034(7) 0.0177(7) -0.0005(7) C3 0.0737(11) 0.0625(10) 0.0539(10) 0.0150(8) 0.0117(8) 0.0013(8) C4 0.1007(14) 0.0554(10) 0.0496(9) 0.0170(9) 0.0215(10) 0.0094(8) C5 0.0906(13) 0.0447(8) 0.0593(10) 0.0020(8) 0.0332(10) 0.0046(7) C6 0.0705(10) 0.0386(8) 0.0481(9) -0.0005(6) 0.0274(8) -0.0013(6) C7 0.0611(9) 0.0413(8) 0.0568(9) -0.0043(6) 0.0282(8) -0.0057(6) C8 0.0720(12) 0.0604(10) 0.0792(12) -0.0163(8) 0.0407(10) -0.0073(8) C9 0.0612(11) 0.0771(12) 0.0918(14) -0.0198(9) 0.0346(11) -0.0196(10) C10 0.0524(10) 0.0738(11) 0.0743(12) -0.0040(8) 0.0137(8) -0.0173(9) C11 0.0564(10) 0.0591(9) 0.0546(9) -0.0038(7) 0.0152(8) -0.0033(7) C12 0.0496(9) 0.0439(8) 0.0504(8) -0.0049(6) 0.0198(7) -0.0054(6) C13 0.0462(8) 0.0453(8) 0.0447(8) 0.0011(6) 0.0164(6) 0.0032(6) C14 0.0561(9) 0.0482(8) 0.0482(8) -0.0075(6) 0.0182(7) -0.0033(6) C15 0.0581(9) 0.0550(9) 0.0429(8) 0.0048(7) 0.0186(7) 0.0010(6) C16 0.0516(8) 0.0478(8) 0.0533(9) 0.0028(6) 0.0229(7) 0.0073(7) C17 0.0598(10) 0.0487(9) 0.0612(10) -0.0096(7) 0.0222(8) -0.0031(7) C18 0.0598(9) 0.0547(9) 0.0450(8) -0.0074(7) 0.0175(7) -0.0058(7) N1 0.0496(7) 0.0520(7) 0.0435(7) -0.0044(5) 0.0161(5) 0.0042(5) N2 0.0738(9) 0.0626(9) 0.0701(10) -0.0020(7) 0.0352(8) 0.0108(7) O1 0.1509(14) 0.1021(11) 0.1075(11) -0.0644(10) 0.0594(10) -0.0006(9) O2 0.1411(12) 0.0842(9) 0.0703(9) -0.0066(8) 0.0596(8) 0.0102(7) 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' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag C2 C1 N1 129.43(12) ? C2 C1 C6 122.02(13) ? N1 C1 C6 108.49(13) ? C3 C2 C1 117.28(14) ? C3 C2 H2 121.4 ? C1 C2 H2 121.4 ? C2 C3 C4 121.75(16) ? C2 C3 H3 119.1 ? C4 C3 H3 119.1 ? C5 C4 C3 120.95(15) ? C5 C4 H4 119.5 ? C3 C4 H4 119.5 ? C4 C5 C6 118.86(15) ? C4 C5 H5 120.6 ? C6 C5 H5 120.6 ? C5 C6 C1 119.14(15) ? C5 C6 C7 133.65(14) ? C1 C6 C7 107.21(12) ? C8 C7 C12 119.29(15) ? C8 C7 C6 133.67(14) ? C12 C7 C6 107.03(12) ? C9 C8 C7 118.80(16) ? C9 C8 H8 120.6 ? C7 C8 H8 120.6 ? C8 C9 C10 121.23(15) ? C8 C9 H9 119.4 ? C10 C9 H9 119.4 ? C11 C10 C9 121.36(17) ? C11 C10 H10 119.3 ? C9 C10 H10 119.3 ? C10 C11 C12 117.57(15) ? C10 C11 H11 121.2 ? C12 C11 H11 121.2 ? C11 C12 C7 121.74(13) ? C11 C12 N1 129.41(13) ? C7 C12 N1 108.74(12) ? C14 C13 C18 120.06(12) ? C14 C13 N1 119.35(12) ? C18 C13 N1 120.59(12) ? C15 C14 C13 120.15(13) ? C15 C14 H14 119.9 ? C13 C14 H14 119.9 ? C16 C15 C14 118.67(13) ? C16 C15 H15 120.7 ? C14 C15 H15 120.7 ? C17 C16 C15 122.22(12) ? C17 C16 N2 119.67(14) ? C15 C16 N2 118.11(13) ? C16 C17 C18 119.02(13) ? C16 C17 H17 120.5 ? C18 C17 H17 120.5 ? C17 C18 C13 119.88(13) ? C17 C18 H18 120.1 ? C13 C18 H18 120.1 ? C1 N1 C12 108.52(11) y C1 N1 C13 126.25(11) y C12 N1 C13 125.13(11) y O2 N2 O1 123.10(14) y O2 N2 C16 118.63(14) y O1 N2 C16 118.26(15) y loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag C1 C2 1.385(2) ? C1 N1 1.4004(18) y C1 C6 1.4080(19) ? C2 C3 1.376(2) ? C2 H2 0.93 ? C3 C4 1.389(2) ? C3 H3 0.93 ? C4 C5 1.376(2) ? C4 H4 0.93 ? C5 C6 1.392(2) ? C5 H5 0.93 ? C6 C7 1.448(2) ? C7 C8 1.394(2) ? C7 C12 1.4033(19) ? C8 C9 1.369(2) ? C8 H8 0.93 ? C9 C10 1.389(2) ? C9 H9 0.93 ? C10 C11 1.375(2) ? C10 H10 0.93 ? C11 C12 1.386(2) ? C11 H11 0.93 ? C12 N1 1.4037(18) y C13 C14 1.3877(19) ? C13 C18 1.3879(19) ? C13 N1 1.4181(16) y C14 C15 1.3790(19) ? C14 H14 0.93 ? C15 C16 1.377(2) ? C15 H15 0.93 ? C16 C17 1.372(2) ? C16 N2 1.4692(18) y C17 C18 1.3798(19) ? C17 H17 0.93 ? C18 H18 0.93 ? N2 O2 1.2086(17) y N2 O1 1.2123(18) y 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 C11 H11 O2 3_666 0.93 2.52 3.396(2) 157 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 _geom_torsion_publ_flag N1 C1 C2 C3 177.02(13) ? C6 C1 C2 C3 0.2(2) ? C1 C2 C3 C4 0.5(2) ? C2 C3 C4 C5 -0.8(2) ? C3 C4 C5 C6 0.5(2) ? C4 C5 C6 C1 0.2(2) ? C4 C5 C6 C7 -178.38(14) ? C2 C1 C6 C5 -0.5(2) ? N1 C1 C6 C5 -177.93(12) ? C2 C1 C6 C7 178.40(12) ? N1 C1 C6 C7 0.99(14) ? C5 C6 C7 C8 -4.1(3) ? C1 C6 C7 C8 177.16(15) ? C5 C6 C7 C12 177.29(15) ? C1 C6 C7 C12 -1.40(14) ? C12 C7 C8 C9 0.8(2) ? C6 C7 C8 C9 -177.63(15) ? C7 C8 C9 C10 -0.1(2) ? C8 C9 C10 C11 -0.4(3) ? C9 C10 C11 C12 0.3(2) ? C10 C11 C12 C7 0.4(2) ? C10 C11 C12 N1 176.18(14) ? C8 C7 C12 C11 -0.9(2) ? C6 C7 C12 C11 177.87(12) ? C8 C7 C12 N1 -177.51(12) ? C6 C7 C12 N1 1.29(14) ? C18 C13 C14 C15 1.0(2) ? N1 C13 C14 C15 -178.41(12) ? C13 C14 C15 C16 -0.7(2) ? C14 C15 C16 C17 0.0(2) ? C14 C15 C16 N2 179.75(12) ? C15 C16 C17 C18 0.4(2) ? N2 C16 C17 C18 -179.33(12) ? C16 C17 C18 C13 -0.1(2) ? C14 C13 C18 C17 -0.6(2) ? N1 C13 C18 C17 178.83(12) ? C2 C1 N1 C12 -177.36(13) ? C6 C1 N1 C12 -0.20(14) ? C2 C1 N1 C13 -0.8(2) ? C6 C1 N1 C13 176.33(12) ? C11 C12 N1 C1 -176.94(14) ? C7 C12 N1 C1 -0.70(14) ? C11 C12 N1 C13 6.5(2) ? C7 C12 N1 C13 -177.28(12) ? C14 C13 N1 C1 -126.76(15) y C18 C13 N1 C1 53.81(19) y C14 C13 N1 C12 49.21(18) y C18 C13 N1 C12 -130.22(14) y C17 C16 N2 O2 -175.13(14) y C15 C16 N2 O2 5.1(2) ? C17 C16 N2 O1 6.2(2) ? C15 C16 N2 O1 -173.49(15) y _cod_database_fobs_code 2206656