Supplementary Material (ESI) for Organic and Biomolecular Chemistry This journal is (C) The Royal Society of Chemistry 2006 data_global _journal_name_full Org.Biomol.Chem. _journal_coden_cambridge 0177 loop_ _publ_author_name 'Hans-Joachim Knolker ' 'Anne Jager ' 'Micha P. Krahl ' 'Tilo Krause ' _publ_contact_author_email HANS-JOACHIM.KNOELKER@CHEMIE.TU-DRESDEN.DE data_tilo38 _database_code_depnum_ccdc_archive 'CCDC 609677' _audit_creation_method SHELXL-97 _chemical_name_systematic 7-hydroxy-9H-carbazole-3-carbaldehyde _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C13 H9 N O2' _chemical_formula_sum 'C13 H9 N O2' _chemical_formula_weight 211.21 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_int_tables_number 14 _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 7.381(1) _cell_length_b 11.493(1) _cell_length_c 11.058(1) _cell_angle_alpha 90.00 _cell_angle_beta 95.02(1) _cell_angle_gamma 90.00 _cell_volume 934.45(17) _cell_formula_units_Z 4 _cell_measurement_temperature 198(2) _cell_measurement_reflns_used 129 _cell_measurement_theta_min 5.80 _cell_measurement_theta_max 21.40 _exptl_crystal_description block _exptl_crystal_colour 'light brown' _exptl_crystal_size_max 0.42 _exptl_crystal_size_mid 0.16 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.501 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 440 _exptl_absorpt_coefficient_mu 0.103 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8665 _exptl_absorpt_correction_T_max 0.9878 _exptl_absorpt_process_details 'SADABS version 2.10 (Sheldrick, Bruker AXS Inc.,2002)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 198(2) _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method \f _diffrn_detector_area_resol_mean 9 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 25734 _diffrn_reflns_av_R_equivalents 0.0442 _diffrn_reflns_av_sigmaI/netI 0.0221 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 3.29 _diffrn_reflns_theta_max 30.00 _reflns_number_total 2704 _reflns_number_gt 2059 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1999)' _computing_cell_refinement 'Dirax/lsq (Duisenberg, 1992)' _computing_data_reduction 'EvalCCD (Duisenberg et al., 2003)' _computing_structure_solution 'SIR2004 (Burla et al., 2005)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997), WinGX (Farrugia, 1999), PLATON (Spek, 2005)' _computing_molecular_graphics 'ORTEP-3 for Windows (Farrugia, 1997), SCHAKAL99 (Keller & Pierrard, 1999)' _computing_publication_material 'WinGX (Farrugia, 1999), enCIFer (Allen et al., 2004)' _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^ > 2sigma(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. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0636P)^2^+0.2531P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2704 _refine_ls_number_parameters 153 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0608 _refine_ls_R_factor_gt 0.0414 _refine_ls_wR_factor_ref 0.1192 _refine_ls_wR_factor_gt 0.1062 _refine_ls_goodness_of_fit_ref 1.054 _refine_ls_restrained_S_all 1.054 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.41068(17) 0.63192(11) 0.71732(11) 0.0217(2) Uani 1 1 d . . . H1 H 0.4679 0.6068 0.7931 0.026 Uiso 1 1 calc R . . C2 C 0.38777(17) 0.74856(11) 0.69037(11) 0.0220(3) Uani 1 1 d . . . H2 H 0.4283 0.8048 0.7496 0.026 Uiso 1 1 calc R . . C3 C 0.30579(16) 0.78629(10) 0.57728(11) 0.0205(2) Uani 1 1 d . . . C4 C 0.24352(16) 0.70572(10) 0.48806(10) 0.0193(2) Uani 1 1 d . . . H4 H 0.1890 0.7312 0.4116 0.023 Uiso 1 1 calc R . . C4A C 0.26306(15) 0.58836(10) 0.51353(10) 0.0173(2) Uani 1 1 d . . . C4B C 0.21347(15) 0.48291(10) 0.44715(10) 0.0176(2) Uani 1 1 d . . . C5 C 0.13203(16) 0.45946(10) 0.33119(10) 0.0200(2) Uani 1 1 d . . . H5 H 0.0977 0.5214 0.2771 0.024 Uiso 1 1 calc R . . C6 C 0.10181(17) 0.34577(10) 0.29568(11) 0.0211(2) Uani 1 1 d . . . H6 H 0.0466 0.3294 0.2167 0.025 Uiso 1 1 calc R . . C7 C 0.15177(17) 0.25406(10) 0.37510(11) 0.0198(2) Uani 1 1 d . . . C8 C 0.23592(16) 0.27367(10) 0.49060(10) 0.0198(2) Uani 1 1 d . . . H8 H 0.2709 0.2113 0.5440 0.024 Uiso 1 1 calc R . . C8A C 0.26667(15) 0.38926(10) 0.52451(10) 0.0178(2) Uani 1 1 d . . . C9A C 0.34598(16) 0.55268(10) 0.62829(10) 0.0184(2) Uani 1 1 d . . . N9 N 0.34576(14) 0.43323(9) 0.63367(9) 0.0201(2) Uani 1 1 d . . . C10 C 0.28540(19) 0.91049(11) 0.55601(12) 0.0266(3) Uani 1 1 d . . . H10 H 0.3289 0.9614 0.6198 0.032 Uiso 1 1 calc R . . O11 O 0.21675(17) 0.95450(9) 0.46259(10) 0.0394(3) Uani 1 1 d . . . O12 O 0.11448(14) 0.14429(8) 0.33198(9) 0.0279(2) Uani 1 1 d . . . H12 H 0.156(3) 0.0895(18) 0.385(2) 0.053(6) Uiso 1 1 d . . . H9N H 0.412(3) 0.3954(16) 0.6916(18) 0.045(5) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0246(6) 0.0208(6) 0.0187(5) 0.0002(4) -0.0038(4) -0.0004(4) C2 0.0250(6) 0.0181(5) 0.0222(6) -0.0025(4) -0.0021(4) -0.0020(4) C3 0.0230(6) 0.0156(5) 0.0225(5) -0.0004(4) -0.0008(4) -0.0002(4) C4 0.0227(6) 0.0152(5) 0.0193(5) 0.0012(4) -0.0017(4) 0.0013(4) C4A 0.0185(5) 0.0157(5) 0.0175(5) 0.0003(4) -0.0001(4) 0.0007(4) C4B 0.0198(5) 0.0145(5) 0.0181(5) 0.0009(4) 0.0000(4) 0.0017(4) C5 0.0240(6) 0.0167(5) 0.0186(5) 0.0021(4) -0.0024(4) 0.0023(4) C6 0.0251(6) 0.0190(6) 0.0183(5) -0.0002(4) -0.0036(4) 0.0018(4) C7 0.0233(6) 0.0144(5) 0.0211(5) -0.0016(4) -0.0008(4) 0.0007(4) C8 0.0244(6) 0.0157(5) 0.0186(5) 0.0020(4) -0.0024(4) 0.0019(4) C8A 0.0196(5) 0.0158(5) 0.0175(5) 0.0003(4) -0.0007(4) 0.0004(4) C9A 0.0199(5) 0.0161(5) 0.0188(5) 0.0010(4) -0.0002(4) 0.0001(4) N9 0.0265(5) 0.0151(4) 0.0175(4) 0.0018(4) -0.0047(4) 0.0008(4) C10 0.0351(7) 0.0162(5) 0.0275(6) -0.0015(5) -0.0030(5) 0.0008(5) O11 0.0644(7) 0.0192(5) 0.0320(5) 0.0035(4) -0.0108(5) 0.0045(5) O12 0.0420(6) 0.0138(4) 0.0258(4) -0.0029(3) -0.0089(4) 0.0014(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_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.3805(17) . ? C1 C9A 1.3944(16) . ? C1 H1 0.9500 . ? C2 C3 1.4091(16) . ? C2 H2 0.9500 . ? C3 C4 1.4010(16) . ? C3 C10 1.4525(17) . ? C4 C4A 1.3829(16) . ? C4 H4 0.9500 . ? C4A C9A 1.4203(15) . ? C4A C4B 1.4473(16) . ? C4B C5 1.3940(15) . ? C4B C8A 1.4091(15) . ? C5 C6 1.3770(16) . ? C5 H5 0.9500 . ? C6 C7 1.4006(16) . ? C6 H6 0.9500 . ? C7 O12 1.3681(14) . ? C7 C8 1.3889(15) . ? C8 C8A 1.3936(16) . ? C8 H8 0.9500 . ? C8A N9 1.3892(14) . ? C9A N9 1.3742(15) . ? N9 H9N 0.887(19) . ? C10 O11 1.2199(16) . ? C10 H10 0.9500 . ? O12 H12 0.89(2) . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C9A 117.00(11) . . ? C2 C1 H1 121.5 . . ? C9A C1 H1 121.5 . . ? C1 C2 C3 121.69(11) . . ? C1 C2 H2 119.2 . . ? C3 C2 H2 119.2 . . ? C4 C3 C2 120.70(11) . . ? C4 C3 C10 120.84(11) . . ? C2 C3 C10 118.46(11) . . ? C4A C4 C3 118.64(10) . . ? C4A C4 H4 120.7 . . ? C3 C4 H4 120.7 . . ? C4 C4A C9A 119.52(10) . . ? C4 C4A C4B 134.12(10) . . ? C9A C4A C4B 106.35(10) . . ? C5 C4B C8A 119.05(10) . . ? C5 C4B C4A 134.27(10) . . ? C8A C4B C4A 106.68(10) . . ? C6 C5 C4B 119.47(10) . . ? C6 C5 H5 120.3 . . ? C4B C5 H5 120.3 . . ? C5 C6 C7 120.54(10) . . ? C5 C6 H6 119.7 . . ? C7 C6 H6 119.7 . . ? O12 C7 C8 122.03(10) . . ? O12 C7 C6 116.20(10) . . ? C8 C7 C6 121.77(10) . . ? C7 C8 C8A 116.83(10) . . ? C7 C8 H8 121.6 . . ? C8A C8 H8 121.6 . . ? N9 C8A C8 128.80(10) . . ? N9 C8A C4B 108.86(10) . . ? C8 C8A C4B 122.32(10) . . ? N9 C9A C1 128.58(11) . . ? N9 C9A C4A 108.97(10) . . ? C1 C9A C4A 122.44(11) . . ? C9A N9 C8A 109.14(10) . . ? C9A N9 H9N 121.2(12) . . ? C8A N9 H9N 127.9(12) . . ? O11 C10 C3 125.04(12) . . ? O11 C10 H10 117.5 . . ? C3 C10 H10 117.5 . . ? C7 O12 H12 112.1(13) . . ? 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C9A C1 C2 C3 -1.13(19) . . . . ? C1 C2 C3 C4 0.34(19) . . . . ? C1 C2 C3 C10 179.60(12) . . . . ? C2 C3 C4 C4A 0.42(18) . . . . ? C10 C3 C4 C4A -178.82(12) . . . . ? C3 C4 C4A C9A -0.34(17) . . . . ? C3 C4 C4A C4B 178.55(12) . . . . ? C4 C4A C4B C5 2.2(2) . . . . ? C9A C4A C4B C5 -178.78(13) . . . . ? C4 C4A C4B C8A -178.47(13) . . . . ? C9A C4A C4B C8A 0.52(13) . . . . ? C8A C4B C5 C6 1.38(17) . . . . ? C4A C4B C5 C6 -179.39(13) . . . . ? C4B C5 C6 C7 0.16(19) . . . . ? C5 C6 C7 O12 179.34(12) . . . . ? C5 C6 C7 C8 -1.24(19) . . . . ? O12 C7 C8 C8A -179.92(11) . . . . ? C6 C7 C8 C8A 0.70(18) . . . . ? C7 C8 C8A N9 179.33(11) . . . . ? C7 C8 C8A C4B 0.90(18) . . . . ? C5 C4B C8A N9 179.34(10) . . . . ? C4A C4B C8A N9 -0.08(13) . . . . ? C5 C4B C8A C8 -1.95(18) . . . . ? C4A C4B C8A C8 178.62(11) . . . . ? C2 C1 C9A N9 -177.43(12) . . . . ? C2 C1 C9A C4A 1.22(18) . . . . ? C4 C4A C9A N9 178.39(11) . . . . ? C4B C4A C9A N9 -0.78(13) . . . . ? C4 C4A C9A C1 -0.50(18) . . . . ? C4B C4A C9A C1 -179.66(11) . . . . ? C1 C9A N9 C8A 179.54(12) . . . . ? C4A C9A N9 C8A 0.74(14) . . . . ? C8 C8A N9 C9A -179.01(12) . . . . ? C4B C8A N9 C9A -0.41(13) . . . . ? C4 C3 C10 O11 -0.6(2) . . . . ? C2 C3 C10 O11 -179.85(14) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O12 H12 O11 0.89(2) 1.81(2) 2.6876(13) 166(2) 1_545 N9 H9N O12 0.887(19) 2.106(19) 2.9624(13) 162.0(17) 4_666 _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.364 _refine_diff_density_min -0.259 _refine_diff_density_rms 0.054 _chemical_compound_source synthesis # Attachment 'Compound3_methyl 7-methoxy-9H-carbazole-3-carboxylate_anne7.cif' data_an7 _database_code_depnum_ccdc_archive 'CCDC 609678' _audit_creation_method SHELXL-97 _chemical_name_systematic 'methyl 7-methoxy-9H-carbazole-3-carboxylate' _chemical_name_common 'Clausine C (Clauszoline L)' _chemical_melting_point 468 _chemical_formula_moiety 'C15 H13 N O3' _chemical_formula_sum 'C15 H13 N O3' _chemical_formula_weight 255.26 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' _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_int_tables_number 2 _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 8.118(3) _cell_length_b 9.020(2) _cell_length_c 9.143(3) _cell_angle_alpha 101.10(2) _cell_angle_beta 102.27(3) _cell_angle_gamma 104.33(3) _cell_volume 612.2(4) _cell_formula_units_Z 2 _cell_measurement_temperature 198(2) _cell_measurement_reflns_used 21 _cell_measurement_theta_min 4.80 _cell_measurement_theta_max 18.58 _exptl_crystal_description plate _exptl_crystal_colour 'light yellow' _exptl_crystal_size_max 0.28 _exptl_crystal_size_mid 0.11 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.385 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 268 _exptl_absorpt_coefficient_mu 0.097 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.7754 _exptl_absorpt_correction_T_max 0.9961 _exptl_absorpt_process_details 'SADABS version 2.10 (Sheldrick, Bruker AXS Inc.,2002)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 198(2) _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method \f _diffrn_detector_area_resol_mean 9 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 14687 _diffrn_reflns_av_R_equivalents 0.0536 _diffrn_reflns_av_sigmaI/netI 0.0305 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_theta_min 3.03 _diffrn_reflns_theta_max 25.40 _reflns_number_total 2242 _reflns_number_gt 1792 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1999)' _computing_cell_refinement 'Dirax/lsq (Duisenberg, 1992)' _computing_data_reduction 'EvalCCD (Duisenberg et al., 2003)' _computing_structure_solution 'SIR2004 (Burla et al., 2005)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997), WinGX (Farrugia, 1999), PLATON (Spek, 2005)' _computing_molecular_graphics 'ORTEP-3 for Windows (Farrugia, 1997), SCHAKAL99 (Keller & Pierrard, 1999)' _computing_publication_material 'WinGX (Farrugia, 1999), enCIFer (Allen et al., 2004)' _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^ > 2sigma(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. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0596P)^2^+0.2620P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2242 _refine_ls_number_parameters 178 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0612 _refine_ls_R_factor_gt 0.0450 _refine_ls_wR_factor_ref 0.1255 _refine_ls_wR_factor_gt 0.1141 _refine_ls_goodness_of_fit_ref 1.097 _refine_ls_restrained_S_all 1.097 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.6818(3) 0.6549(2) 0.4197(2) 0.0341(5) Uani 1 1 d . . . H1 H 0.6182 0.5549 0.3489 0.041 Uiso 1 1 calc R . . C2 C 0.6505(3) 0.7917(2) 0.3917(2) 0.0316(4) Uani 1 1 d . . . H2 H 0.5639 0.7859 0.3009 0.038 Uiso 1 1 calc R . . C3 C 0.7456(2) 0.9400(2) 0.4965(2) 0.0275(4) Uani 1 1 d . . . C4 C 0.8708(2) 0.9519(2) 0.6309(2) 0.0265(4) Uani 1 1 d . . . H4 H 0.9336 1.0523 0.7013 0.032 Uiso 1 1 calc R . . C4A C 0.9038(2) 0.8149(2) 0.6621(2) 0.0260(4) Uani 1 1 d . . . C4B C 1.0225(2) 0.7818(2) 0.7847(2) 0.0274(4) Uani 1 1 d . . . C5 C 1.1462(3) 0.8709(2) 0.9261(2) 0.0353(5) Uani 1 1 d . . . H5 H 1.1678 0.9823 0.9579 0.042 Uiso 1 1 calc R . . C6 C 1.2353(3) 0.7965(2) 1.0176(2) 0.0387(5) Uani 1 1 d . . . H6 H 1.3174 0.8569 1.1140 0.046 Uiso 1 1 calc R . . C7 C 1.2075(3) 0.6319(2) 0.9715(2) 0.0325(4) Uani 1 1 d . . . C8 C 1.0861(2) 0.5393(2) 0.8342(2) 0.0288(4) Uani 1 1 d . . . H8 H 1.0661 0.4282 0.8026 0.035 Uiso 1 1 calc R . . C8A C 0.9944(2) 0.6168(2) 0.7444(2) 0.0265(4) Uani 1 1 d . . . C9A C 0.8086(2) 0.6669(2) 0.5537(2) 0.0278(4) Uani 1 1 d . . . N9 N 0.8644(2) 0.55052(19) 0.60570(19) 0.0306(4) Uani 1 1 d . . . C10 C 0.7143(2) 1.0863(2) 0.4648(2) 0.0288(4) Uani 1 1 d . . . O11 O 0.79121(19) 1.21814(15) 0.54742(17) 0.0397(4) Uani 1 1 d . . . O12 O 0.58899(18) 1.05863(16) 0.33187(17) 0.0389(4) Uani 1 1 d . . . C13 C 0.5510(3) 1.1954(2) 0.2908(3) 0.0409(5) Uani 1 1 d . . . H13A H 0.5115 1.2522 0.3726 0.061 Uiso 1 1 calc R . . H13B H 0.4577 1.1614 0.1929 0.061 Uiso 1 1 calc R . . H13C H 0.6579 1.2656 0.2790 0.061 Uiso 1 1 calc R . . O14 O 1.30837(19) 0.57363(17) 1.07185(17) 0.0415(4) Uani 1 1 d . . . C15 C 1.2891(3) 0.4081(3) 1.0284(3) 0.0415(5) Uani 1 1 d . . . H15A H 1.1658 0.3475 1.0131 0.062 Uiso 1 1 calc R . . H15B H 1.3659 0.3809 1.1105 0.062 Uiso 1 1 calc R . . H15C H 1.3224 0.3825 0.9318 0.062 Uiso 1 1 calc R . . H9N H 0.826(3) 0.456(3) 0.565(3) 0.045(7) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0410(11) 0.0208(9) 0.0311(10) 0.0001(7) -0.0029(8) 0.0092(8) C2 0.0362(10) 0.0248(10) 0.0286(10) 0.0035(8) 0.0002(8) 0.0100(8) C3 0.0294(9) 0.0217(9) 0.0321(10) 0.0077(7) 0.0091(8) 0.0079(7) C4 0.0276(9) 0.0175(8) 0.0318(10) 0.0028(7) 0.0072(8) 0.0059(7) C4A 0.0262(9) 0.0213(9) 0.0282(10) 0.0038(7) 0.0068(7) 0.0056(7) C4B 0.0292(9) 0.0222(9) 0.0293(10) 0.0045(7) 0.0064(8) 0.0083(7) C5 0.0382(11) 0.0227(10) 0.0365(11) 0.0007(8) 0.0008(9) 0.0077(8) C6 0.0382(11) 0.0320(11) 0.0344(11) 0.0004(8) -0.0042(9) 0.0087(9) C7 0.0310(10) 0.0341(11) 0.0331(10) 0.0108(8) 0.0055(8) 0.0120(8) C8 0.0317(10) 0.0225(9) 0.0324(11) 0.0071(8) 0.0077(8) 0.0094(8) C8A 0.0279(9) 0.0228(9) 0.0276(9) 0.0047(7) 0.0067(8) 0.0078(7) C9A 0.0317(10) 0.0192(9) 0.0321(10) 0.0049(7) 0.0078(8) 0.0091(7) N9 0.0366(9) 0.0178(8) 0.0313(9) 0.0018(6) -0.0005(7) 0.0091(7) C10 0.0297(9) 0.0234(10) 0.0345(10) 0.0089(8) 0.0093(8) 0.0084(7) O11 0.0471(9) 0.0205(7) 0.0451(9) 0.0054(6) 0.0025(7) 0.0097(6) O12 0.0418(8) 0.0261(7) 0.0449(9) 0.0120(6) 0.0018(7) 0.0098(6) C13 0.0435(12) 0.0322(11) 0.0493(13) 0.0182(9) 0.0064(10) 0.0147(9) O14 0.0426(8) 0.0378(8) 0.0389(8) 0.0103(6) -0.0034(7) 0.0150(7) C15 0.0451(12) 0.0392(12) 0.0435(12) 0.0170(9) 0.0056(10) 0.0189(9) _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_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.379(3) . ? C1 C9A 1.390(3) . ? C1 H1 0.9500 . ? C2 C3 1.408(3) . ? C2 H2 0.9500 . ? C3 C4 1.386(3) . ? C3 C10 1.474(3) . ? C4 C4A 1.395(2) . ? C4 H4 0.9500 . ? C4A C9A 1.420(2) . ? C4A C4B 1.444(3) . ? C4B C5 1.405(3) . ? C4B C8A 1.410(2) . ? C5 C6 1.370(3) . ? C5 H5 0.9500 . ? C6 C7 1.409(3) . ? C6 H6 0.9500 . ? C7 O14 1.367(2) . ? C7 C8 1.381(3) . ? C8 C8A 1.391(3) . ? C8 H8 0.9500 . ? C8A N9 1.381(3) . ? C9A N9 1.367(2) . ? N9 H9N 0.81(3) . ? C10 O11 1.209(2) . ? C10 O12 1.344(2) . ? O12 C13 1.440(2) . ? C13 H13A 0.9800 . ? C13 H13B 0.9800 . ? C13 H13C 0.9800 . ? O14 C15 1.429(3) . ? C15 H15A 0.9800 . ? C15 H15B 0.9800 . ? C15 H15C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C9A 118.47(18) . . ? C2 C1 H1 120.8 . . ? C9A C1 H1 120.8 . . ? C1 C2 C3 120.64(18) . . ? C1 C2 H2 119.7 . . ? C3 C2 H2 119.7 . . ? C4 C3 C2 120.93(17) . . ? C4 C3 C10 118.55(17) . . ? C2 C3 C10 120.51(17) . . ? C3 C4 C4A 119.40(16) . . ? C3 C4 H4 120.3 . . ? C4A C4 H4 120.3 . . ? C4 C4A C9A 118.77(17) . . ? C4 C4A C4B 134.86(17) . . ? C9A C4A C4B 106.35(15) . . ? C5 C4B C8A 117.61(17) . . ? C5 C4B C4A 135.83(17) . . ? C8A C4B C4A 106.53(16) . . ? C6 C5 C4B 119.64(18) . . ? C6 C5 H5 120.2 . . ? C4B C5 H5 120.2 . . ? C5 C6 C7 121.14(19) . . ? C5 C6 H6 119.4 . . ? C7 C6 H6 119.4 . . ? O14 C7 C8 123.70(18) . . ? O14 C7 C6 115.08(18) . . ? C8 C7 C6 121.22(18) . . ? C7 C8 C8A 116.69(17) . . ? C7 C8 H8 121.7 . . ? C8A C8 H8 121.7 . . ? N9 C8A C8 127.62(17) . . ? N9 C8A C4B 108.73(16) . . ? C8 C8A C4B 123.65(17) . . ? N9 C9A C1 129.44(17) . . ? N9 C9A C4A 108.78(17) . . ? C1 C9A C4A 121.77(17) . . ? C9A N9 C8A 109.60(16) . . ? C9A N9 H9N 126.5(17) . . ? C8A N9 H9N 123.9(17) . . ? O11 C10 O12 122.52(17) . . ? O11 C10 C3 124.79(18) . . ? O12 C10 C3 112.69(16) . . ? C10 O12 C13 116.48(16) . . ? O12 C13 H13A 109.5 . . ? O12 C13 H13B 109.5 . . ? H13A C13 H13B 109.5 . . ? O12 C13 H13C 109.5 . . ? H13A C13 H13C 109.5 . . ? H13B C13 H13C 109.5 . . ? C7 O14 C15 117.37(16) . . ? O14 C15 H15A 109.5 . . ? O14 C15 H15B 109.5 . . ? H15A C15 H15B 109.5 . . ? O14 C15 H15C 109.5 . . ? H15A C15 H15C 109.5 . . ? H15B C15 H15C 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 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C9A C1 C2 C3 0.3(3) . . . . ? C1 C2 C3 C4 -0.9(3) . . . . ? C1 C2 C3 C10 178.81(18) . . . . ? C2 C3 C4 C4A 0.5(3) . . . . ? C10 C3 C4 C4A -179.25(16) . . . . ? C3 C4 C4A C9A 0.5(3) . . . . ? C3 C4 C4A C4B 178.80(19) . . . . ? C4 C4A C4B C5 4.0(4) . . . . ? C9A C4A C4B C5 -177.5(2) . . . . ? C4 C4A C4B C8A -178.0(2) . . . . ? C9A C4A C4B C8A 0.4(2) . . . . ? C8A C4B C5 C6 0.8(3) . . . . ? C4A C4B C5 C6 178.5(2) . . . . ? C4B C5 C6 C7 1.1(3) . . . . ? C5 C6 C7 O14 178.40(19) . . . . ? C5 C6 C7 C8 -1.7(3) . . . . ? O14 C7 C8 C8A -179.71(17) . . . . ? C6 C7 C8 C8A 0.4(3) . . . . ? C7 C8 C8A N9 -178.29(18) . . . . ? C7 C8 C8A C4B 1.5(3) . . . . ? C5 C4B C8A N9 177.73(17) . . . . ? C4A C4B C8A N9 -0.7(2) . . . . ? C5 C4B C8A C8 -2.1(3) . . . . ? C4A C4B C8A C8 179.49(16) . . . . ? C2 C1 C9A N9 -179.1(2) . . . . ? C2 C1 C9A C4A 0.8(3) . . . . ? C4 C4A C9A N9 178.72(16) . . . . ? C4B C4A C9A N9 0.0(2) . . . . ? C4 C4A C9A C1 -1.2(3) . . . . ? C4B C4A C9A C1 -179.91(18) . . . . ? C1 C9A N9 C8A 179.5(2) . . . . ? C4A C9A N9 C8A -0.4(2) . . . . ? C8 C8A N9 C9A -179.47(18) . . . . ? C4B C8A N9 C9A 0.7(2) . . . . ? C4 C3 C10 O11 0.6(3) . . . . ? C2 C3 C10 O11 -179.16(19) . . . . ? C4 C3 C10 O12 -179.47(16) . . . . ? C2 C3 C10 O12 0.8(2) . . . . ? O11 C10 O12 C13 0.6(3) . . . . ? C3 C10 O12 C13 -179.37(16) . . . . ? C8 C7 O14 C15 1.9(3) . . . . ? C6 C7 O14 C15 -178.22(18) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.40 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.169 _refine_diff_density_min -0.269 _refine_diff_density_rms 0.055 _chemical_compound_source synthesis # Attachment 'Compound10_2-methoxy-6-methyl-9H-carbazole_anne11.cif' data_an11 _database_code_depnum_ccdc_archive 'CCDC 609679' _audit_creation_method SHELXL-97 _chemical_name_systematic 2-methoxy-6-methyl-9H-carbazole _chemical_name_common ? _chemical_melting_point 500-501 _chemical_formula_moiety 'C14 H13 N O' _chemical_formula_sum 'C14 H13 N O' _chemical_formula_weight 211.25 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' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_int_tables_number 14 _symmetry_space_group_name_Hall '-P 2ybc' 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' _cell_length_a 22.924(3) _cell_length_b 5.7870(1) _cell_length_c 8.0200(1) _cell_angle_alpha 90.00 _cell_angle_beta 96.98(3) _cell_angle_gamma 90.00 _cell_volume 1056.06(16) _cell_formula_units_Z 4 _cell_measurement_temperature 198(2) _cell_measurement_reflns_used 580 _cell_measurement_theta_min 4.45 _cell_measurement_theta_max 30.87 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.69 _exptl_crystal_size_mid 0.55 _exptl_crystal_size_min 0.25 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.329 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 448 _exptl_absorpt_coefficient_mu 0.084 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.8160 _exptl_absorpt_correction_T_max 0.9794 _exptl_absorpt_process_details 'SADABS version 2.10 (Sheldrick, Bruker AXS Inc.,2002)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 198(2) _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method \f _diffrn_detector_area_resol_mean 9 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 13562 _diffrn_reflns_av_R_equivalents 0.0280 _diffrn_reflns_av_sigmaI/netI 0.0179 _diffrn_reflns_limit_h_min -27 _diffrn_reflns_limit_h_max 27 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 3.58 _diffrn_reflns_theta_max 25.40 _reflns_number_total 1915 _reflns_number_gt 1618 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1999)' _computing_cell_refinement 'Dirax/lsq (Duisenberg, 1992)' _computing_data_reduction 'EvalCCD (Duisenberg et al., 2003)' _computing_structure_solution 'SIR2004 (Burla et al., 2005)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997), WinGX (Farrugia, 1999), PLATON (Spek, 2005)' _computing_molecular_graphics 'ORTEP-3 for Windows (Farrugia, 1997), SCHAKAL99 (Keller & Pierrard, 1999)' _computing_publication_material 'WinGX (Farrugia, 1999), enCIFer (Allen et al., 2004)' _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^ > 2sigma(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. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0539P)^2^+0.7421P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1915 _refine_ls_number_parameters 151 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0566 _refine_ls_R_factor_gt 0.0457 _refine_ls_wR_factor_ref 0.1277 _refine_ls_wR_factor_gt 0.1179 _refine_ls_goodness_of_fit_ref 1.103 _refine_ls_restrained_S_all 1.103 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.34740(8) 0.7257(3) 1.1203(2) 0.0325(4) Uani 1 1 d . . . H1 H 0.3495 0.8681 1.1796 0.039 Uiso 1 1 calc R . . C2 C 0.39563(8) 0.5815(4) 1.1253(2) 0.0354(5) Uani 1 1 d . . . H2 H 0.4315 0.6283 1.1883 0.042 Uiso 1 1 calc R . . C3 C 0.39368(8) 0.3681(4) 1.0407(2) 0.0341(5) Uani 1 1 d . . . C4 C 0.34181(8) 0.3003(3) 0.9471(2) 0.0306(4) Uani 1 1 d . . . H4 H 0.3398 0.1566 0.8894 0.037 Uiso 1 1 calc R . . C4A C 0.29235(8) 0.4434(3) 0.9374(2) 0.0270(4) Uani 1 1 d . . . C4B C 0.23374(8) 0.4299(3) 0.8492(2) 0.0266(4) Uani 1 1 d . . . C5 C 0.20390(8) 0.2714(3) 0.7386(2) 0.0294(4) Uani 1 1 d . . . H5 H 0.2227 0.1325 0.7113 0.035 Uiso 1 1 calc R . . C6 C 0.14712(8) 0.3170(3) 0.6691(2) 0.0320(4) Uani 1 1 d . . . H6 H 0.1270 0.2099 0.5928 0.038 Uiso 1 1 calc R . . C7 C 0.11866(8) 0.5214(3) 0.7104(2) 0.0303(4) Uani 1 1 d . . . O O 0.06260(6) 0.5463(2) 0.63174(17) 0.0389(4) Uani 1 1 d . . . C8 C 0.14648(8) 0.6814(3) 0.8217(2) 0.0296(4) Uani 1 1 d . . . H8 H 0.1270 0.8173 0.8517 0.035 Uiso 1 1 calc R . . C8A C 0.20429(8) 0.6339(3) 0.8876(2) 0.0269(4) Uani 1 1 d . . . N9 N 0.24209(7) 0.7665(3) 0.9944(2) 0.0310(4) Uani 1 1 d . . . C9A C 0.29591(8) 0.6553(3) 1.0257(2) 0.0280(4) Uani 1 1 d . . . C10 C 0.44738(9) 0.2163(4) 1.0560(3) 0.0464(6) Uani 1 1 d . . . H10A H 0.4527 0.1441 1.1673 0.070 Uiso 1 1 calc R . . H10B H 0.4820 0.3099 1.0410 0.070 Uiso 1 1 calc R . . H10C H 0.4424 0.0959 0.9695 0.070 Uiso 1 1 calc R . . C11 C 0.03122(9) 0.7483(4) 0.6690(3) 0.0444(5) Uani 1 1 d . . . H11A H 0.0292 0.7565 0.7902 0.067 Uiso 1 1 calc R . . H11B H -0.0087 0.7423 0.6093 0.067 Uiso 1 1 calc R . . H11C H 0.0515 0.8854 0.6331 0.067 Uiso 1 1 calc R . . H9N H 0.2333(9) 0.894(4) 1.043(3) 0.042(6) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0399(10) 0.0279(10) 0.0300(10) -0.0004(8) 0.0058(8) -0.0023(8) C2 0.0340(10) 0.0360(11) 0.0358(10) 0.0038(8) 0.0027(8) -0.0028(8) C3 0.0349(10) 0.0326(11) 0.0359(10) 0.0062(8) 0.0090(8) 0.0021(8) C4 0.0389(10) 0.0224(9) 0.0319(9) 0.0027(7) 0.0101(8) 0.0035(7) C4A 0.0350(9) 0.0219(9) 0.0255(8) 0.0028(7) 0.0097(7) 0.0003(7) C4B 0.0361(10) 0.0221(9) 0.0231(8) 0.0030(7) 0.0099(7) 0.0018(7) C5 0.0419(11) 0.0211(9) 0.0266(9) -0.0001(7) 0.0091(7) -0.0002(8) C6 0.0419(11) 0.0251(10) 0.0293(9) -0.0030(7) 0.0061(8) -0.0043(8) C7 0.0325(9) 0.0301(10) 0.0286(9) 0.0025(8) 0.0055(7) -0.0024(8) O 0.0352(7) 0.0377(8) 0.0427(8) -0.0042(6) 0.0003(6) 0.0007(6) C8 0.0358(10) 0.0244(9) 0.0296(9) -0.0005(7) 0.0087(7) 0.0034(7) C8A 0.0355(9) 0.0218(9) 0.0244(8) 0.0007(7) 0.0081(7) -0.0005(7) N9 0.0369(9) 0.0240(8) 0.0322(8) -0.0073(7) 0.0054(6) 0.0030(7) C9A 0.0342(9) 0.0245(9) 0.0265(9) 0.0021(7) 0.0087(7) 0.0006(7) C10 0.0398(12) 0.0411(13) 0.0576(14) 0.0011(10) 0.0032(10) 0.0076(9) C11 0.0371(11) 0.0425(12) 0.0523(13) -0.0030(10) 0.0001(9) 0.0071(9) _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_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag C1 C2 1.382(3) . ? C1 C9A 1.385(3) . ? C1 H1 0.9500 . ? C2 C3 1.407(3) . ? C2 H2 0.9500 . ? C3 C4 1.384(3) . ? C3 C10 1.505(3) . ? C4 C4A 1.398(3) . ? C4 H4 0.9500 . ? C4A C9A 1.413(3) . ? C4A C4B 1.443(3) . ? C4B C5 1.396(3) . ? C4B C8A 1.412(2) . ? C5 C6 1.378(3) . ? C5 H5 0.9500 . ? C6 C7 1.410(3) . ? C6 H6 0.9500 . ? C7 O 1.369(2) . ? C7 C8 1.386(3) . ? O C11 1.424(3) . ? C8 C8A 1.393(3) . ? C8 H8 0.9500 . ? C8A N9 1.376(2) . ? N9 C9A 1.387(2) . ? N9 H9N 0.87(3) . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? C11 H11A 0.9800 . ? C11 H11B 0.9800 . ? C11 H11C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C9A 117.65(18) . . ? C2 C1 H1 121.2 . . ? C9A C1 H1 121.2 . . ? C1 C2 C3 122.51(18) . . ? C1 C2 H2 118.7 . . ? C3 C2 H2 118.7 . . ? C4 C3 C2 119.02(18) . . ? C4 C3 C10 121.28(19) . . ? C2 C3 C10 119.70(18) . . ? C3 C4 C4A 120.00(18) . . ? C3 C4 H4 120.0 . . ? C4A C4 H4 120.0 . . ? C4 C4A C9A 119.26(17) . . ? C4 C4A C4B 134.10(17) . . ? C9A C4A C4B 106.62(15) . . ? C5 C4B C8A 118.52(16) . . ? C5 C4B C4A 134.62(17) . . ? C8A C4B C4A 106.82(15) . . ? C6 C5 C4B 119.81(17) . . ? C6 C5 H5 120.1 . . ? C4B C5 H5 120.1 . . ? C5 C6 C7 120.48(17) . . ? C5 C6 H6 119.8 . . ? C7 C6 H6 119.8 . . ? O C7 C8 124.01(17) . . ? O C7 C6 114.54(16) . . ? C8 C7 C6 121.45(17) . . ? C7 O C11 117.37(15) . . ? C7 C8 C8A 117.03(17) . . ? C7 C8 H8 121.5 . . ? C8A C8 H8 121.5 . . ? N9 C8A C8 128.62(17) . . ? N9 C8A C4B 108.70(16) . . ? C8 C8A C4B 122.68(17) . . ? C8A N9 C9A 109.42(16) . . ? C8A N9 H9N 126.1(15) . . ? C9A N9 H9N 124.3(15) . . ? C1 C9A N9 129.99(18) . . ? C1 C9A C4A 121.55(17) . . ? N9 C9A C4A 108.44(16) . . ? C3 C10 H10A 109.5 . . ? C3 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C3 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? O C11 H11A 109.5 . . ? O C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? O C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 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 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C9A C1 C2 C3 -0.9(3) . . . . ? C1 C2 C3 C4 0.8(3) . . . . ? C1 C2 C3 C10 -178.12(18) . . . . ? C2 C3 C4 C4A 0.1(3) . . . . ? C10 C3 C4 C4A 178.96(18) . . . . ? C3 C4 C4A C9A -0.8(3) . . . . ? C3 C4 C4A C4B 177.49(18) . . . . ? C4 C4A C4B C5 -0.8(3) . . . . ? C9A C4A C4B C5 177.64(19) . . . . ? C4 C4A C4B C8A -178.42(19) . . . . ? C9A C4A C4B C8A -0.01(18) . . . . ? C8A C4B C5 C6 0.4(2) . . . . ? C4A C4B C5 C6 -177.06(18) . . . . ? C4B C5 C6 C7 -0.7(3) . . . . ? C5 C6 C7 O 179.52(16) . . . . ? C5 C6 C7 C8 -0.3(3) . . . . ? C8 C7 O C11 -0.7(3) . . . . ? C6 C7 O C11 179.53(17) . . . . ? O C7 C8 C8A -178.20(16) . . . . ? C6 C7 C8 C8A 1.6(3) . . . . ? C7 C8 C8A N9 177.37(17) . . . . ? C7 C8 C8A C4B -1.9(3) . . . . ? C5 C4B C8A N9 -178.43(15) . . . . ? C4A C4B C8A N9 -0.33(19) . . . . ? C5 C4B C8A C8 1.0(3) . . . . ? C4A C4B C8A C8 179.10(16) . . . . ? C8 C8A N9 C9A -178.82(17) . . . . ? C4B C8A N9 C9A 0.6(2) . . . . ? C2 C1 C9A N9 -177.84(18) . . . . ? C2 C1 C9A C4A 0.2(3) . . . . ? C8A N9 C9A C1 177.65(18) . . . . ? C8A N9 C9A C4A -0.6(2) . . . . ? C4 C4A C9A C1 0.6(3) . . . . ? C4B C4A C9A C1 -178.05(16) . . . . ? C4 C4A C9A N9 179.04(15) . . . . ? C4B C4A C9A N9 0.35(19) . . . . ? _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 25.40 _diffrn_measured_fraction_theta_full 0.993 _refine_diff_density_max 0.674 _refine_diff_density_min -0.159 _refine_diff_density_rms 0.044 _chemical_compound_source synthesis # Attachment 'Compound11_3-bromo-2-methoxy-6-methyl-9H-carbazole_anne13.cif' data_an13 _database_code_depnum_ccdc_archive 'CCDC 609680' _audit_creation_method SHELXL-97 _chemical_name_systematic 3-bromo-2-methoxy-6-methyl-9H-carbazole _chemical_name_common ? _chemical_melting_point 444 _chemical_formula_moiety 'C14 H12 Br N O' _chemical_formula_sum 'C14 H12 Br N O' _chemical_formula_weight 290.16 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' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21' _symmetry_int_tables_number 4 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z' _cell_length_a 6.642(1) _cell_length_b 7.761(1) _cell_length_c 11.984(5) _cell_angle_alpha 90.00 _cell_angle_beta 105.13(3) _cell_angle_gamma 90.00 _cell_volume 596.3(3) _cell_formula_units_Z 2 _cell_measurement_temperature 198(2) _cell_measurement_reflns_used 134 _cell_measurement_theta_min 3.166 _cell_measurement_theta_max 23.068 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.36 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.616 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 292 _exptl_absorpt_coefficient_mu 3.428 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5645 _exptl_absorpt_correction_T_max 0.7711 _exptl_absorpt_process_details 'SADABS version 2.10 (Sheldrick, Bruker AXS Inc.,2002)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 198(2) _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type KappaCCD _diffrn_measurement_method \f _diffrn_detector_area_resol_mean 9 _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 16713 _diffrn_reflns_av_R_equivalents 0.0289 _diffrn_reflns_av_sigmaI/netI 0.0223 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 3.16 _diffrn_reflns_theta_max 30.00 _reflns_number_total 3380 _reflns_number_gt 3122 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Collect (Nonius BV, 1999)' _computing_cell_refinement 'Dirax/lsq (Duisenberg, 1992)' _computing_data_reduction 'EvalCCD (Duisenberg et al., 2003)' _computing_structure_solution 'SIR2004 (Burla et al., 2005)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997), WinGX (Farrugia, 1999), PLATON (Spek, 2005)' _computing_molecular_graphics 'ORTEP-3 for Windows (Farrugia, 1997), SCHAKAL99 (Keller & Pierrard, 1999)' _computing_publication_material 'WinGX (Farrugia, 1999), enCIFer (Allen et al., 2004)' _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^ > 2sigma(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. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0207P)^2^+0.0769P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.005(6) _refine_ls_number_reflns 3380 _refine_ls_number_parameters 160 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0269 _refine_ls_R_factor_gt 0.0220 _refine_ls_wR_factor_ref 0.0453 _refine_ls_wR_factor_gt 0.0440 _refine_ls_goodness_of_fit_ref 1.084 _refine_ls_restrained_S_all 1.084 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Br Br 0.46777(2) 0.13792(3) 0.959220(13) 0.03538(5) Uani 1 1 d . . . C1 C 0.2353(3) 0.4337(2) 0.32046(17) 0.0342(4) Uani 1 1 d . . . H1 H 0.3109 0.4948 0.2759 0.041 Uiso 1 1 calc R . . C2 C 0.0363(3) 0.3749(2) 0.27183(16) 0.0325(4) Uani 1 1 d . . . H2 H -0.0248 0.3963 0.1921 0.039 Uiso 1 1 calc R . . C3 C -0.0808(3) 0.2842(2) 0.33538(15) 0.0292(3) Uani 1 1 d . . . C4 C 0.0075(3) 0.2512(2) 0.45176(14) 0.0273(3) Uani 1 1 d . . . H4 H -0.0690 0.1901 0.4959 0.033 Uiso 1 1 calc R . . C4A C 0.2105(3) 0.3086(2) 0.50373(15) 0.0258(3) Uani 1 1 d . . . C4B C 0.3465(3) 0.2987(2) 0.61965(15) 0.0258(3) Uani 1 1 d . . . C5 C 0.3272(3) 0.2269(2) 0.72269(15) 0.0262(3) Uani 1 1 d . . . H5 H 0.2040 0.1667 0.7254 0.031 Uiso 1 1 calc R . . C6 C 0.4899(3) 0.2443(2) 0.82116(15) 0.0270(3) Uani 1 1 d . . . C7 C 0.6744(3) 0.3360(2) 0.81911(16) 0.0289(3) Uani 1 1 d . . . C8 C 0.6962(3) 0.4061(2) 0.71722(18) 0.0319(4) Uani 1 1 d . . . H8 H 0.8191 0.4666 0.7145 0.038 Uiso 1 1 calc R . . C8A C 0.5326(3) 0.3855(2) 0.61846(16) 0.0285(3) Uani 1 1 d . . . C9A C 0.3219(3) 0.4004(2) 0.43753(16) 0.0293(4) Uani 1 1 d . . . N9 N 0.5154(2) 0.4447(2) 0.50825(16) 0.0331(3) Uani 1 1 d . . . C10 C -0.2979(3) 0.2250(3) 0.27701(17) 0.0344(4) Uani 1 1 d . . . H10A H -0.2917 0.1146 0.2384 0.052 Uiso 1 1 calc R . . H10B H -0.3666 0.3109 0.2197 0.052 Uiso 1 1 calc R . . H10C H -0.3773 0.2110 0.3348 0.052 Uiso 1 1 calc R . . O11 O 0.82113(19) 0.34566(19) 0.92279(12) 0.0369(3) Uani 1 1 d . . . C12 C 0.9990(3) 0.4513(3) 0.9274(2) 0.0462(5) Uani 1 1 d . . . H12A H 1.0761 0.4054 0.8745 0.069 Uiso 1 1 calc R . . H12B H 1.0897 0.4519 1.0063 0.069 Uiso 1 1 calc R . . H12C H 0.9535 0.5692 0.9045 0.069 Uiso 1 1 calc R . . H9N H 0.599(4) 0.510(4) 0.493(2) 0.049(7) Uiso 1 1 d . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br 0.03704(8) 0.03594(8) 0.03393(8) 0.00494(11) 0.01067(6) -0.00227(11) C1 0.0398(10) 0.0286(9) 0.0414(10) 0.0129(8) 0.0237(8) 0.0064(7) C2 0.0378(9) 0.0278(9) 0.0345(8) 0.0076(7) 0.0145(8) 0.0078(7) C3 0.0334(8) 0.0222(8) 0.0349(9) 0.0001(7) 0.0142(7) 0.0053(6) C4 0.0321(8) 0.0201(7) 0.0340(9) 0.0016(6) 0.0163(7) 0.0002(6) C4A 0.0298(8) 0.0186(7) 0.0335(8) 0.0009(6) 0.0164(7) 0.0018(6) C4B 0.0276(7) 0.0180(7) 0.0361(9) -0.0006(6) 0.0160(7) -0.0010(6) C5 0.0261(8) 0.0202(8) 0.0356(9) -0.0011(7) 0.0142(7) -0.0027(6) C6 0.0303(8) 0.0199(7) 0.0343(9) -0.0004(7) 0.0146(7) 0.0000(6) C7 0.0260(8) 0.0220(8) 0.0409(9) -0.0051(7) 0.0126(7) 0.0001(6) C8 0.0266(8) 0.0253(8) 0.0477(10) -0.0031(8) 0.0167(8) -0.0052(6) C8A 0.0293(8) 0.0195(7) 0.0418(9) 0.0004(7) 0.0186(7) -0.0008(6) C9A 0.0312(9) 0.0211(8) 0.0410(9) 0.0034(7) 0.0193(8) 0.0015(6) N9 0.0310(8) 0.0300(8) 0.0436(8) 0.0055(7) 0.0194(7) -0.0062(7) C10 0.0358(9) 0.0306(9) 0.0358(10) 0.0024(8) 0.0079(8) 0.0005(7) O11 0.0298(6) 0.0375(7) 0.0428(7) -0.0029(6) 0.0084(6) -0.0064(5) C12 0.0290(9) 0.0574(14) 0.0514(12) -0.0075(10) 0.0090(8) -0.0131(9) _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_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Br C6 1.8890(18) . ? C1 C2 1.376(3) . ? C1 C9A 1.395(3) . ? C1 H1 0.9500 . ? C2 C3 1.411(2) . ? C2 H2 0.9500 . ? C3 C4 1.389(3) . ? C3 C10 1.501(2) . ? C4 C4A 1.402(2) . ? C4 H4 0.9500 . ? C4A C9A 1.411(2) . ? C4A C4B 1.448(3) . ? C4B C5 1.391(2) . ? C4B C8A 1.412(2) . ? C5 C6 1.383(3) . ? C5 H5 0.9500 . ? C6 C7 1.423(2) . ? C7 O11 1.366(2) . ? C7 C8 1.378(3) . ? C8 C8A 1.391(3) . ? C8 H8 0.9500 . ? C8A N9 1.375(3) . ? C9A N9 1.386(3) . ? N9 H9N 0.80(3) . ? C10 H10A 0.9800 . ? C10 H10B 0.9800 . ? C10 H10C 0.9800 . ? O11 C12 1.428(2) . ? C12 H12A 0.9800 . ? C12 H12B 0.9800 . ? C12 H12C 0.9800 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C2 C1 C9A 117.60(16) . . ? C2 C1 H1 121.2 . . ? C9A C1 H1 121.2 . . ? C1 C2 C3 122.75(17) . . ? C1 C2 H2 118.6 . . ? C3 C2 H2 118.6 . . ? C4 C3 C2 119.10(17) . . ? C4 C3 C10 120.96(16) . . ? C2 C3 C10 119.94(16) . . ? C3 C4 C4A 119.52(16) . . ? C3 C4 H4 120.2 . . ? C4A C4 H4 120.2 . . ? C4 C4A C9A 119.69(16) . . ? C4 C4A C4B 134.09(15) . . ? C9A C4A C4B 106.21(15) . . ? C5 C4B C8A 118.95(16) . . ? C5 C4B C4A 133.98(15) . . ? C8A C4B C4A 107.07(14) . . ? C6 C5 C4B 119.07(15) . . ? C6 C5 H5 120.5 . . ? C4B C5 H5 120.5 . . ? C5 C6 C7 121.26(16) . . ? C5 C6 Br 118.84(12) . . ? C7 C6 Br 119.87(14) . . ? O11 C7 C8 124.68(15) . . ? O11 C7 C6 115.14(16) . . ? C8 C7 C6 120.18(17) . . ? C7 C8 C8A 117.98(15) . . ? C7 C8 H8 121.0 . . ? C8A C8 H8 121.0 . . ? N9 C8A C8 129.03(16) . . ? N9 C8A C4B 108.41(16) . . ? C8 C8A C4B 122.53(16) . . ? N9 C9A C1 129.99(16) . . ? N9 C9A C4A 108.68(16) . . ? C1 C9A C4A 121.33(17) . . ? C8A N9 C9A 109.64(15) . . ? C8A N9 H9N 122.3(18) . . ? C9A N9 H9N 127.1(18) . . ? C3 C10 H10A 109.5 . . ? C3 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C3 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C7 O11 C12 116.95(16) . . ? O11 C12 H12A 109.5 . . ? O11 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? O11 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 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 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C9A C1 C2 C3 0.1(3) . . . . ? C1 C2 C3 C4 -0.4(3) . . . . ? C1 C2 C3 C10 179.48(17) . . . . ? C2 C3 C4 C4A 0.1(2) . . . . ? C10 C3 C4 C4A -179.82(16) . . . . ? C3 C4 C4A C9A 0.5(2) . . . . ? C3 C4 C4A C4B 179.35(17) . . . . ? C4 C4A C4B C5 0.7(3) . . . . ? C9A C4A C4B C5 179.67(18) . . . . ? C4 C4A C4B C8A -178.57(18) . . . . ? C9A C4A C4B C8A 0.37(18) . . . . ? C8A C4B C5 C6 0.7(2) . . . . ? C4A C4B C5 C6 -178.51(17) . . . . ? C4B C5 C6 C7 0.9(2) . . . . ? C4B C5 C6 Br -177.25(12) . . . . ? C5 C6 C7 O11 179.00(14) . . . . ? Br C6 C7 O11 -2.9(2) . . . . ? C5 C6 C7 C8 -1.6(3) . . . . ? Br C6 C7 C8 176.51(13) . . . . ? O11 C7 C8 C8A 179.99(16) . . . . ? C6 C7 C8 C8A 0.6(3) . . . . ? C7 C8 C8A N9 178.98(18) . . . . ? C7 C8 C8A C4B 1.0(3) . . . . ? C5 C4B C8A N9 179.95(15) . . . . ? C4A C4B C8A N9 -0.63(19) . . . . ? C5 C4B C8A C8 -1.7(3) . . . . ? C4A C4B C8A C8 177.73(16) . . . . ? C2 C1 C9A N9 -179.47(17) . . . . ? C2 C1 C9A C4A 0.5(3) . . . . ? C4 C4A C9A N9 179.14(15) . . . . ? C4B C4A C9A N9 0.02(18) . . . . ? C4 C4A C9A C1 -0.8(3) . . . . ? C4B C4A C9A C1 -179.95(16) . . . . ? C8 C8A N9 C9A -177.56(18) . . . . ? C4B C8A N9 C9A 0.7(2) . . . . ? C1 C9A N9 C8A 179.54(19) . . . . ? C4A C9A N9 C8A -0.4(2) . . . . ? C8 C7 O11 C12 6.9(3) . . . . ? C6 C7 O11 C12 -173.72(17) . . . . ? _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 30.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.230 _refine_diff_density_min -0.353 _refine_diff_density_rms 0.051 _chemical_compound_source synthesis