#------------------------------------------------------------------------------ #$Date: 2021-05-27 06:53:17 +0300 (Thu, 27 May 2021) $ #$Revision: 265532 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/15/80/7158099.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_7158099 loop_ _publ_author_name 'Li, Fangyi' 'Zhao, Lan' 'Qiu, Changfu' 'Zhao, Lixin' 'Yin, Guangwei' 'Wang, Chunhua' 'Li, Zheng' _publ_section_title ; Base-promoted, CBr4-mediated tandem bromination/intramolecular Friedel-Crafts alkylation of N-aryl enamines: a facile access to 1H- and 3H-indoles ; _journal_name_full 'Organic & Biomolecular Chemistry' _journal_paper_doi 10.1039/D1OB00731A _journal_year 2021 _chemical_formula_moiety 'C19 H18 Br N O2' _chemical_formula_sum 'C19 H18 Br N O2' _chemical_formula_weight 372.25 _chemical_name_systematic 'Ethyl 6-bromo-4,7-dimethyl-2-phenyl-1H-indole-3-carboxylate' _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2ybc' _space_group_name_H-M_alt 'P 1 21/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary dual _audit_creation_date 2021-05-24 _audit_creation_method ; Olex2 1.2-ac3 (compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381) ; _audit_update_record ; 2021-05-24 deposited with the CCDC. 2021-05-26 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90.5451(16) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 12.1783(2) _cell_length_b 7.56305(18) _cell_length_c 17.6627(3) _cell_measurement_reflns_used 3677 _cell_measurement_temperature 159.99(10) _cell_measurement_theta_max 76.0030 _cell_measurement_theta_min 3.6050 _cell_volume 1626.75(5) _computing_cell_refinement 'CrysAlisPro 1.171.39.45g (Rigaku OD, 2018)' _computing_data_collection 'CrysAlisPro 1.171.39.45g (Rigaku OD, 2018)' _computing_data_reduction 'CrysAlisPro 1.171.39.45g (Rigaku OD, 2018)' _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2015)' _computing_structure_solution 'ShelXT (Sheldrick, 2015)' _diffrn_ambient_environment N~2~ _diffrn_ambient_temperature 159.99(10) _diffrn_detector 'CCD plate' _diffrn_detector_type HyPix _diffrn_measured_fraction_theta_full 0.996 _diffrn_measured_fraction_theta_max 0.946 _diffrn_measurement_details ; List of Runs (angles in degrees, time in seconds): # Type Start End Width t~exp~ \w \q \k \f Frames #-------------------------------------------------------------------------- 1 \w -49.00 22.00 0.50 2.28 -- -47.00 24.00 52.00 142 2 \w 34.00 121.00 0.50 2.28 -- 47.00 24.00 52.00 174 3 \w 106.00 177.00 0.50 9.10 -- 107.61 24.00 52.00 142 4 \w 93.00 178.00 0.50 9.10 -- 107.61 19.00 120.00 170 5 \w 74.00 122.00 0.50 9.10 -- 107.61 -24.00-111.00 96 6 \w 64.00 106.00 0.50 9.10 -- 107.61 -99.00 0.00 84 7 \w 46.00 85.00 0.50 9.10 -- 107.61 -99.00 30.00 78 8 \w 36.00 108.00 0.50 9.10 -- 107.61 -99.00-120.00 144 9 \w -7.00 18.00 0.50 2.28 -- 47.00 -24.00-111.00 50 10 \w -89.00 -35.00 0.50 2.28 -- -47.00 125.00 120.00 108 11 \w -101.00 -27.00 0.50 9.10 -- -100.00 125.00 150.00 148 12 \w -80.00 -54.00 0.50 9.10 -- -100.00 24.00 52.00 52 13 \w -117.00 -33.00 0.50 2.28 -- -47.00 -24.00-111.00 168 14 \w -131.00 -86.00 0.50 9.10 -- -100.00 -24.00-111.00 90 15 \w -61.00 -33.00 0.50 9.10 -- -100.00 125.00 -90.00 56 16 \w -99.00 -73.00 0.50 9.10 -- -100.00 125.00 -90.00 52 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'ROD, Synergy Custom system, HyPix' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 -0.0738818000 _diffrn_orient_matrix_UB_12 -0.0567663000 _diffrn_orient_matrix_UB_13 0.0660268000 _diffrn_orient_matrix_UB_21 0.0956473000 _diffrn_orient_matrix_UB_22 0.0317398000 _diffrn_orient_matrix_UB_23 0.0560680000 _diffrn_orient_matrix_UB_31 -0.0373388000 _diffrn_orient_matrix_UB_32 0.1930829000 _diffrn_orient_matrix_UB_33 0.0101459000 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0757 _diffrn_reflns_av_unetI/netI 0.0681 _diffrn_reflns_Laue_measured_fraction_full 0.996 _diffrn_reflns_Laue_measured_fraction_max 0.946 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_number 9497 _diffrn_reflns_point_group_measured_fraction_full 0.996 _diffrn_reflns_point_group_measured_fraction_max 0.946 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 76.360 _diffrn_reflns_theta_min 3.630 _diffrn_source 'Rotating-anode X-ray tube' _diffrn_source_type 'Rigaku (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 3.516 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.58839 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.39.45g (Rigaku Oxford Diffraction, 2018) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour 'clear light colourless' _exptl_crystal_density_diffrn 1.520 _exptl_crystal_description block _exptl_crystal_F_000 760 _exptl_crystal_recrystallization_method 'Re-crystallisation from solvent' _exptl_crystal_size_max 0.05 _exptl_crystal_size_mid 0.03 _exptl_crystal_size_min 0.03 _refine_diff_density_max 1.019 _refine_diff_density_min -1.297 _refine_diff_density_rms 0.146 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.098 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 211 _refine_ls_number_reflns 3234 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.098 _refine_ls_R_factor_all 0.0847 _refine_ls_R_factor_gt 0.0641 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.1273P)^2^+0.4850P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1701 _refine_ls_wR_factor_ref 0.1987 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2463 _reflns_number_total 3234 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d1ob00731a2.cif _cod_data_source_block lfy_100k_32 _cod_original_cell_volume 1626.75(6) _cod_database_code 7158099 _shelx_shelxl_version_number 2018/1 _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _shelx_estimated_absorpt_t_max 0.902 _shelx_estimated_absorpt_t_min 0.844 _reflns_odcompleteness_completeness 99.94 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 66.49 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups, All N(H) groups At 1.5 times of: All C(H,H,H) groups 2.a Secondary CH2 refined with riding coordinates: C10(H10A,H10B) 2.b Aromatic/amide H refined with riding coordinates: N1(H1), C1(H1A), C2(H2), C6(H6), C12(H12), C14(H14), C16(H16) 2.c Idealised Me refined as rotating group: C8(H8A,H8B,H8C), C9(H9A,H9B,H9C), C19(H19A,H19B,H19C) ; _shelx_res_file ; TITL lfy_100k_32_a.res in P2(1)/c lfy_100k_32.res created by SHELXL-2018/1 at 08:34:50 on 24-May-2021 REM Old TITL LFY_100K_32 in P2(1)/c REM SHELXT solution in P2(1)/c REM R1 0.134, Rweak 0.003, Alpha 0.057, Orientation as input REM Formula found by SHELXT: C19 N O2 Br CELL 1.54184 12.17832 7.563052 17.662663 90 90.5451 90 ZERR 4 0.00021 0.000179 0.000334 0 0.0016 0 LATT 1 SYMM -X,0.5+Y,0.5-Z SFAC C H Br N O UNIT 76 72 4 4 8 L.S. 10 PLAN 20 SIZE 0.03 0.03 0.05 BOND $H LIST 4 fmap 2 acta OMIT -10 5 8 OMIT -6 8 3 REM REM REM WGHT 0.127300 0.485000 FVAR 1.19976 BR1 3 0.822572 0.650011 0.562852 11.00000 0.03991 0.04997 = 0.03094 -0.00476 -0.01017 -0.00325 O1 5 0.634221 0.296016 0.130694 11.00000 0.02527 0.04595 = 0.02981 -0.00720 -0.00027 -0.00753 O2 5 0.794636 0.425336 0.157604 11.00000 0.02145 0.04204 = 0.03071 -0.00547 -0.00015 -0.00166 N1 4 0.541535 0.561014 0.333691 11.00000 0.02006 0.03838 = 0.02208 -0.00017 -0.00163 0.00121 AFIX 43 H1 2 0.482134 0.598408 0.354208 11.00000 -1.20000 AFIX 0 C1 1 0.353898 0.587653 0.098948 11.00000 0.03185 0.04352 = 0.03025 -0.00121 -0.00980 0.00729 AFIX 43 H1A 2 0.354902 0.637653 0.050855 11.00000 -1.20000 AFIX 0 C2 1 0.255613 0.447051 0.198711 11.00000 0.01964 0.04559 = 0.04476 -0.00649 -0.00123 -0.00159 AFIX 43 H2 2 0.190434 0.401152 0.217432 11.00000 -1.20000 AFIX 0 C3 1 0.666561 0.607147 0.442852 11.00000 0.03159 0.02841 = 0.02943 0.00475 -0.00246 -0.00264 C4 1 0.656357 0.450645 0.248063 11.00000 0.02107 0.03493 = 0.02765 -0.00163 -0.00199 -0.00015 C5 1 0.448675 0.503876 0.213693 11.00000 0.02395 0.03626 = 0.02730 -0.00285 -0.00327 0.00518 C6 1 0.449382 0.578508 0.142053 11.00000 0.02517 0.03745 = 0.03266 0.00158 -0.00396 0.00160 AFIX 43 H6 2 0.514578 0.622892 0.122716 11.00000 -1.20000 AFIX 0 C7 1 0.690851 0.381107 0.174108 11.00000 0.02194 0.02922 = 0.03126 0.00156 -0.00358 -0.00017 C8 1 0.916126 0.365492 0.296904 11.00000 0.02369 0.06021 = 0.03616 -0.00067 -0.00655 0.00718 AFIX 137 H8A 2 0.886103 0.263581 0.271779 11.00000 -1.50000 H8B 2 0.975729 0.329810 0.329419 11.00000 -1.50000 H8C 2 0.942534 0.447663 0.259867 11.00000 -1.50000 AFIX 0 C9 1 0.583236 0.689819 0.493697 11.00000 0.03565 0.04116 = 0.02805 -0.00232 -0.00217 -0.00005 AFIX 137 H9A 2 0.604759 0.809027 0.505169 11.00000 -1.50000 H9B 2 0.578684 0.622995 0.539771 11.00000 -1.50000 H9C 2 0.512871 0.690408 0.468731 11.00000 -1.50000 AFIX 0 C10 1 0.835716 0.359075 0.086618 11.00000 0.03410 0.04577 = 0.03412 -0.01058 0.00452 -0.00059 AFIX 23 H10A 2 0.804839 0.426202 0.044743 11.00000 -1.20000 H10B 2 0.815501 0.235895 0.080181 11.00000 -1.20000 AFIX 0 C11 1 0.549401 0.500523 0.261848 11.00000 0.02197 0.02821 = 0.02644 0.00131 -0.00446 -0.00304 C12 1 0.256802 0.521651 0.128088 11.00000 0.02691 0.04560 = 0.03917 -0.00674 -0.01095 0.00131 AFIX 43 H12 2 0.192328 0.528083 0.099580 11.00000 -1.20000 AFIX 0 C13 1 0.719128 0.482044 0.317031 11.00000 0.01966 0.02756 = 0.02992 0.00177 -0.00394 -0.00019 C14 1 0.852650 0.499012 0.416624 11.00000 0.02420 0.03913 = 0.03600 -0.00036 -0.00621 0.00041 AFIX 43 H14 2 0.922913 0.477615 0.435569 11.00000 -1.20000 AFIX 0 C15 1 0.643571 0.553811 0.369432 11.00000 0.02436 0.03239 = 0.02893 0.00549 -0.00402 0.00085 C16 1 0.350864 0.439110 0.242828 11.00000 0.02419 0.03996 = 0.03585 -0.00081 -0.00085 0.00212 AFIX 43 H16 2 0.349107 0.391014 0.291260 11.00000 -1.20000 AFIX 0 C17 1 0.828550 0.452180 0.343278 11.00000 0.02115 0.03948 = 0.03706 0.00499 -0.00643 0.00333 C18 1 0.775266 0.577764 0.463858 11.00000 0.03269 0.04087 = 0.02143 -0.00089 -0.00513 -0.00360 C19 1 0.958596 0.377987 0.088472 11.00000 0.02836 0.07494 = 0.04870 -0.00066 0.00682 0.00727 AFIX 137 H19A 2 0.987780 0.345763 0.040095 11.00000 -1.50000 H19B 2 0.988829 0.301859 0.126842 11.00000 -1.50000 H19C 2 0.977647 0.498415 0.099664 11.00000 -1.50000 AFIX 0 HKLF 4 REM lfy_100k_32_a.res in P2(1)/c REM R1 = 0.0641 for 2463 Fo > 4sig(Fo) and 0.0847 for all 3234 data REM 211 parameters refined using 0 restraints END WGHT 0.1274 0.4819 REM Highest difference peak 1.019, deepest hole -1.297, 1-sigma level 0.146 Q1 1 0.7464 0.6588 0.5844 11.00000 0.05 1.02 Q2 1 0.8852 0.6527 0.5389 11.00000 0.05 0.86 Q3 1 0.8123 0.5373 0.5629 11.00000 0.05 0.79 Q4 1 0.7979 0.7705 0.5609 11.00000 0.05 0.76 Q5 1 0.7578 0.6619 0.5165 11.00000 0.05 0.69 Q6 1 0.9056 0.6454 0.6045 11.00000 0.05 0.67 Q7 1 0.8235 0.0918 0.1059 11.00000 0.05 0.65 Q8 1 0.8503 0.7816 0.5628 11.00000 0.05 0.63 Q9 1 0.8158 0.6016 0.1038 11.00000 0.05 0.61 Q10 1 0.8233 0.6033 0.0220 11.00000 0.05 0.59 Q11 1 0.8240 0.0899 0.0217 11.00000 0.05 0.58 Q12 1 0.7763 0.5974 0.5009 11.00000 0.05 0.54 Q13 1 0.7115 0.5708 0.4646 11.00000 0.05 0.54 Q14 1 0.7816 0.4965 0.3394 11.00000 0.05 0.50 Q15 1 0.6752 0.4359 0.2207 11.00000 0.05 0.45 Q16 1 0.8743 0.6618 0.1607 11.00000 0.05 0.44 Q17 1 0.6803 0.3419 0.0606 11.00000 0.05 0.44 Q18 1 0.5137 0.4753 0.2352 11.00000 0.05 0.43 Q19 1 0.7036 0.4646 0.2741 11.00000 0.05 0.43 Q20 1 0.5936 0.5320 0.3613 11.00000 0.05 0.42 ; _shelx_res_checksum 88423 _olex2_submission_special_instructions 'No special instructions were received' _oxdiff_exptl_absorpt_empirical_details ; Empirical correction (ABSPACK) includes: - Absorption correction using spherical harmonics - Frame scaling ; _oxdiff_exptl_absorpt_empirical_full_max 3.395 _oxdiff_exptl_absorpt_empirical_full_min 0.467 loop_ _space_group_symop_operation_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_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_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group Br1 Br 0.82257(4) 0.65001(8) 0.56285(3) 0.0403(2) Uani 1 1 d . . . . . O1 O 0.6342(2) 0.2960(5) 0.13069(18) 0.0337(8) Uani 1 1 d . . . . . O2 O 0.7946(2) 0.4253(5) 0.15760(18) 0.0314(7) Uani 1 1 d . . . . . N1 N 0.5415(3) 0.5610(6) 0.33369(19) 0.0268(8) Uani 1 1 d . . . . . H1 H 0.482134 0.598408 0.354208 0.032 Uiso 1 1 calc R . . . . C1 C 0.3539(4) 0.5877(8) 0.0989(3) 0.0353(11) Uani 1 1 d . . . . . H1A H 0.354902 0.637653 0.050855 0.042 Uiso 1 1 calc R . . . . C2 C 0.2556(4) 0.4471(8) 0.1987(3) 0.0367(11) Uani 1 1 d . . . . . H2 H 0.190434 0.401152 0.217432 0.044 Uiso 1 1 calc R . . . . C3 C 0.6666(4) 0.6071(7) 0.4429(3) 0.0298(10) Uani 1 1 d . . . . . C4 C 0.6564(3) 0.4506(7) 0.2481(2) 0.0279(9) Uani 1 1 d . . . . . C5 C 0.4487(3) 0.5039(7) 0.2137(2) 0.0292(10) Uani 1 1 d . . . . . C6 C 0.4494(4) 0.5785(7) 0.1421(3) 0.0318(10) Uani 1 1 d . . . . . H6 H 0.514578 0.622892 0.122716 0.038 Uiso 1 1 calc R . . . . C7 C 0.6909(3) 0.3811(6) 0.1741(3) 0.0275(9) Uani 1 1 d . . . . . C8 C 0.9161(4) 0.3655(8) 0.2969(3) 0.0401(13) Uani 1 1 d . . . . . H8A H 0.886103 0.263581 0.271779 0.060 Uiso 1 1 calc GR . . . . H8B H 0.975729 0.329810 0.329419 0.060 Uiso 1 1 calc GR . . . . H8C H 0.942534 0.447663 0.259867 0.060 Uiso 1 1 calc GR . . . . C9 C 0.5832(4) 0.6898(8) 0.4937(3) 0.0350(11) Uani 1 1 d . . . . . H9A H 0.604759 0.809027 0.505169 0.052 Uiso 1 1 calc GR . . . . H9B H 0.578684 0.622995 0.539771 0.052 Uiso 1 1 calc GR . . . . H9C H 0.512871 0.690408 0.468731 0.052 Uiso 1 1 calc GR . . . . C10 C 0.8357(4) 0.3591(8) 0.0866(3) 0.0380(12) Uani 1 1 d . . . . . H10A H 0.804839 0.426202 0.044743 0.046 Uiso 1 1 calc R . . . . H10B H 0.815501 0.235895 0.080181 0.046 Uiso 1 1 calc R . . . . C11 C 0.5494(3) 0.5005(6) 0.2618(2) 0.0256(9) Uani 1 1 d . . . . . C12 C 0.2568(4) 0.5217(8) 0.1281(3) 0.0373(11) Uani 1 1 d . . . . . H12 H 0.192328 0.528083 0.099580 0.045 Uiso 1 1 calc R . . . . C13 C 0.7191(3) 0.4820(6) 0.3170(2) 0.0257(9) Uani 1 1 d . . . . . C14 C 0.8527(4) 0.4990(7) 0.4166(3) 0.0332(10) Uani 1 1 d . . . . . H14 H 0.922913 0.477615 0.435569 0.040 Uiso 1 1 calc R . . . . C15 C 0.6436(3) 0.5538(7) 0.3694(2) 0.0286(10) Uani 1 1 d . . . . . C16 C 0.3509(4) 0.4391(7) 0.2428(3) 0.0333(10) Uani 1 1 d . . . . . H16 H 0.349107 0.391014 0.291260 0.040 Uiso 1 1 calc R . . . . C17 C 0.8285(3) 0.4522(7) 0.3433(3) 0.0326(10) Uani 1 1 d . . . . . C18 C 0.7753(4) 0.5778(7) 0.4639(2) 0.0317(10) Uani 1 1 d . . . . . C19 C 0.9586(4) 0.3780(10) 0.0885(4) 0.0506(15) Uani 1 1 d . . . . . H19A H 0.987780 0.345763 0.040095 0.076 Uiso 1 1 calc GR . . . . H19B H 0.988829 0.301859 0.126842 0.076 Uiso 1 1 calc GR . . . . H19C H 0.977647 0.498415 0.099664 0.076 Uiso 1 1 calc GR . . . . 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 Br1 0.0399(4) 0.0500(4) 0.0309(3) -0.0048(2) -0.0102(2) -0.0032(2) O1 0.0253(14) 0.046(2) 0.0298(16) -0.0072(14) -0.0003(12) -0.0075(14) O2 0.0214(14) 0.042(2) 0.0307(15) -0.0055(14) -0.0001(11) -0.0017(14) N1 0.0201(16) 0.038(2) 0.0221(16) -0.0002(15) -0.0016(12) 0.0012(15) C1 0.032(2) 0.044(3) 0.030(2) -0.001(2) -0.0098(18) 0.007(2) C2 0.020(2) 0.046(3) 0.045(3) -0.006(2) -0.0012(18) -0.002(2) C3 0.032(2) 0.028(3) 0.029(2) 0.0048(18) -0.0025(18) -0.0026(18) C4 0.0211(19) 0.035(3) 0.028(2) -0.0016(18) -0.0020(15) -0.0002(18) C5 0.0239(19) 0.036(3) 0.027(2) -0.0029(18) -0.0033(16) 0.0052(18) C6 0.025(2) 0.037(3) 0.033(2) 0.002(2) -0.0040(16) 0.0016(19) C7 0.0219(19) 0.029(3) 0.031(2) 0.0016(18) -0.0036(16) -0.0002(17) C8 0.024(2) 0.060(4) 0.036(3) -0.001(2) -0.0065(18) 0.007(2) C9 0.036(2) 0.041(3) 0.028(2) -0.002(2) -0.0022(18) 0.000(2) C10 0.034(2) 0.046(3) 0.034(3) -0.011(2) 0.0045(19) -0.001(2) C11 0.0220(19) 0.028(3) 0.026(2) 0.0013(17) -0.0045(15) -0.0030(16) C12 0.027(2) 0.046(3) 0.039(3) -0.007(2) -0.0109(18) 0.001(2) C13 0.0197(18) 0.028(2) 0.030(2) 0.0018(17) -0.0039(15) -0.0002(17) C14 0.024(2) 0.039(3) 0.036(2) 0.000(2) -0.0062(17) 0.0004(19) C15 0.024(2) 0.032(3) 0.029(2) 0.0055(18) -0.0040(16) 0.0008(18) C16 0.024(2) 0.040(3) 0.036(2) -0.001(2) -0.0009(17) 0.002(2) C17 0.0212(19) 0.039(3) 0.037(2) 0.005(2) -0.0064(17) 0.0033(18) C18 0.033(2) 0.041(3) 0.0214(19) -0.0009(19) -0.0051(16) -0.004(2) C19 0.028(2) 0.075(5) 0.049(3) -0.001(3) 0.007(2) 0.007(3) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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' Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 '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_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C7 O2 C10 115.9(4) . . ? C11 N1 H1 125.0 . . ? C11 N1 C15 110.0(4) . . ? C15 N1 H1 125.0 . . ? C6 C1 H1A 120.3 . . ? C6 C1 C12 119.5(5) . . ? C12 C1 H1A 120.3 . . ? C12 C2 H2 119.6 . . ? C12 C2 C16 120.8(4) . . ? C16 C2 H2 119.6 . . ? C15 C3 C9 123.4(4) . . ? C15 C3 C18 112.8(4) . . ? C18 C3 C9 123.8(4) . . ? C11 C4 C7 122.1(4) . . ? C11 C4 C13 107.3(4) . . ? C13 C4 C7 130.6(4) . . ? C6 C5 C11 121.2(4) . . ? C6 C5 C16 119.6(4) . . ? C16 C5 C11 119.2(4) . . ? C1 C6 C5 120.6(4) . . ? C1 C6 H6 119.7 . . ? C5 C6 H6 119.7 . . ? O1 C7 O2 121.8(4) . . ? O1 C7 C4 125.8(4) . . ? O2 C7 C4 112.4(4) . . ? H8A C8 H8B 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C17 C8 H8A 109.5 . . ? C17 C8 H8B 109.5 . . ? C17 C8 H8C 109.5 . . ? C3 C9 H9A 109.5 . . ? C3 C9 H9B 109.5 . . ? C3 C9 H9C 109.5 . . ? H9A C9 H9B 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? O2 C10 H10A 110.2 . . ? O2 C10 H10B 110.2 . . ? O2 C10 C19 107.5(4) . . ? H10A C10 H10B 108.5 . . ? C19 C10 H10A 110.2 . . ? C19 C10 H10B 110.2 . . ? N1 C11 C4 109.5(3) . . ? N1 C11 C5 117.7(4) . . ? C4 C11 C5 132.8(4) . . ? C1 C12 H12 119.9 . . ? C2 C12 C1 120.2(4) . . ? C2 C12 H12 119.9 . . ? C15 C13 C4 105.7(3) . . ? C15 C13 C17 117.3(4) . . ? C17 C13 C4 136.9(4) . . ? C17 C14 H14 118.9 . . ? C17 C14 C18 122.3(4) . . ? C18 C14 H14 118.9 . . ? N1 C15 C13 107.5(4) . . ? C3 C15 N1 125.9(4) . . ? C3 C15 C13 126.6(4) . . ? C2 C16 H16 120.3 . . ? C5 C16 C2 119.3(5) . . ? C5 C16 H16 120.3 . . ? C13 C17 C8 124.0(4) . . ? C14 C17 C8 118.8(4) . . ? C14 C17 C13 117.2(4) . . ? C3 C18 Br1 118.4(4) . . ? C3 C18 C14 123.7(4) . . ? C14 C18 Br1 117.9(3) . . ? C10 C19 H19A 109.5 . . ? C10 C19 H19B 109.5 . . ? C10 C19 H19C 109.5 . . ? H19A C19 H19B 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? 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 Br1 C18 1.915(4) . ? O1 C7 1.211(6) . ? O2 C7 1.342(5) . ? O2 C10 1.444(6) . ? N1 H1 0.8600 . ? N1 C11 1.353(6) . ? N1 C15 1.389(5) . ? C1 H1A 0.9300 . ? C1 C6 1.386(6) . ? C1 C12 1.387(7) . ? C2 H2 0.9300 . ? C2 C12 1.369(8) . ? C2 C16 1.393(6) . ? C3 C9 1.498(7) . ? C3 C15 1.384(6) . ? C3 C18 1.389(6) . ? C4 C7 1.473(6) . ? C4 C11 1.380(6) . ? C4 C13 1.452(6) . ? C5 C6 1.386(7) . ? C5 C11 1.486(6) . ? C5 C16 1.391(7) . ? C6 H6 0.9300 . ? C8 H8A 0.9600 . ? C8 H8B 0.9600 . ? C8 H8C 0.9600 . ? C8 C17 1.502(7) . ? C9 H9A 0.9600 . ? C9 H9B 0.9600 . ? C9 H9C 0.9600 . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C10 C19 1.503(7) . ? C12 H12 0.9300 . ? C13 C15 1.419(6) . ? C13 C17 1.425(6) . ? C14 H14 0.9300 . ? C14 C17 1.372(7) . ? C14 C18 1.398(7) . ? C16 H16 0.9300 . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ?