#------------------------------------------------------------------------------ #$Date: 2024-06-01 01:12:53 +0300 (Sat, 01 Jun 2024) $ #$Revision: 292132 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/57/17/1571735.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_1571735 loop_ _publ_author_name 'Giri, Indrajit' 'Chhetri, Shant' 'John P., Jesslyn' 'Mondal, Madalasa' 'Dey, Arka Bikash' 'Vijayaraghavan, Ratheesh K.' _publ_section_title ; Engineered solid-state aggregates in brickwork stacks of n-type organic semiconductors: a way to achieve high electron mobility ; _journal_name_full 'Chemical Science' _journal_paper_doi 10.1039/D4SC02339K _journal_year 2024 _chemical_formula_moiety 'C30 H36 Br2 N2 O4' _chemical_formula_sum 'C30 H36 Br2 N2 O4' _chemical_formula_weight 648.43 _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary dual _audit_creation_date 2021-09-14 _audit_creation_method ; Olex2 1.3 (compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272) ; _audit_update_record ; 2024-01-08 deposited with the CCDC. 2024-05-20 downloaded from the CCDC. ; _cell_angle_alpha 87.499(2) _cell_angle_beta 87.373(2) _cell_angle_gamma 75.469(2) _cell_formula_units_Z 1 _cell_length_a 5.13630(10) _cell_length_b 7.0488(2) _cell_length_c 20.6300(6) _cell_measurement_reflns_used 3882 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 68.0740 _cell_measurement_theta_min 2.1480 _cell_volume 721.85(3) _computing_cell_refinement 'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)' _computing_data_collection 'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)' _computing_data_reduction 'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)' _computing_molecular_graphics 'Olex2 1.3 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.3 (Dolomanov et al., 2009)' _computing_structure_refinement 'SHELXL 2018/3 (Sheldrick, 2015)' _computing_structure_solution 'SHELXT 2014/4 (Sheldrick, 2014)' _diffrn_ambient_temperature 293(2) _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 10.0000 _diffrn_detector_type HyPix3000 _diffrn_measured_fraction_theta_full 0.986 _diffrn_measured_fraction_theta_max 0.979 _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 80.00 159.00 0.50 0.80 -- 96.67 42.00 -30.00 158 2 \w 82.00 134.00 0.50 0.80 -- 96.67 25.00 60.00 104 3 \w 84.00 164.00 0.50 0.80 -- 96.67 33.00 -60.00 160 4 \w 100.00 140.00 0.50 0.80 -- 96.67 33.00-150.00 80 5 \w 81.00 157.00 0.50 0.80 -- 96.67 50.00-120.00 152 6 \w 67.00 113.00 0.50 0.20 -- 41.33 21.00 90.00 92 7 \w 22.00 60.00 0.50 0.20 -- 41.33 21.00 90.00 76 8 \w -35.00 17.00 0.50 0.20 -- -41.33 43.00 120.00 104 9 \w -37.00 -12.00 0.50 0.20 -- -41.33 32.00 -30.00 50 10 \w -9.00 17.00 0.50 0.20 -- -41.33 32.00 -30.00 52 11 \w -19.00 35.00 0.50 0.20 -- -41.33 11.00-120.00 108 12 \w 46.00 72.00 0.50 0.80 -- 96.67-145.00-150.00 52 13 \w 73.00 123.00 0.50 0.80 -- 96.67-145.00-150.00 100 14 \w 39.00 98.00 0.50 0.20 -- 41.33-135.00 -54.00 118 15 \w 56.00 99.00 0.50 0.80 -- 96.67-135.00 -54.00 86 16 \w 98.00 127.00 0.50 0.80 -- 96.67-145.00 30.00 58 17 \w 39.00 98.00 0.50 0.20 -- 41.33-135.00 124.00 118 18 \w 76.00 102.00 0.50 0.80 -- 96.67-135.00 124.00 52 19 \w 49.00 96.00 0.50 0.80 -- 96.67-145.00 60.00 94 20 \w 56.00 92.00 0.50 0.80 -- 96.67-145.00 30.00 72 21 \w 45.00 106.00 0.50 0.80 -- 96.67 -96.00 -60.00 122 22 \w 25.00 105.00 0.50 0.80 -- 96.67 -96.00-180.00 160 23 \w -28.00 10.00 0.50 0.20 -- 41.33 -11.00 -90.00 76 24 \w 31.00 57.00 0.50 0.80 -- 96.67 -50.00-120.00 52 25 \w 39.00 68.00 0.50 0.80 -- 96.67 -59.00-180.00 58 26 \w 31.00 57.00 0.50 0.80 -- 96.67 -50.00 -90.00 52 27 \w 31.00 83.00 0.50 0.80 -- 96.67 -68.00 -30.00 104 28 \w 30.00 56.00 0.50 0.80 -- 96.67 -50.00 -30.00 52 29 \w 30.00 57.00 0.50 0.80 -- 96.67 -50.00 0.00 54 30 \w 30.00 55.00 0.50 0.80 -- 96.67 -50.00 30.00 50 31 \w 54.00 104.00 0.50 0.80 -- 96.67 -77.00 30.00 100 32 \w 28.00 78.00 0.50 0.80 -- 96.67 -77.00 90.00 100 33 \w 30.00 57.00 0.50 0.80 -- 96.67 -50.00 150.00 54 34 \w 5.00 37.00 0.50 0.20 -- 41.33 -32.00 150.00 64 35 \w 96.00 125.00 0.50 0.80 -- 96.67 145.00-120.00 58 36 \w 102.00 127.00 0.50 0.80 -- 96.67 135.00-169.00 50 37 \w 121.00 169.00 0.50 0.80 -- 96.67 96.00-120.00 96 38 \w 102.00 153.00 0.50 0.80 -- 96.67 117.00 -30.00 102 39 \w 88.00 164.00 0.50 0.80 -- 96.67 135.00 10.00 152 40 \w -107.00 -72.00 0.50 0.20 -- -41.33 -54.00 -30.00 70 41 \w -64.00 -22.00 0.50 0.20 -- -41.33 -54.00 -30.00 84 42 \w -82.00 -56.00 0.50 0.80 -- -82.50 -75.00 141.67 52 43 \w -152.00 -94.00 0.50 0.80 -- -82.50 -75.00 141.67 116 44 \w -150.00 -66.00 0.50 0.80 -- -82.50-135.00 124.00 168 45 \w -149.00-123.00 0.50 0.80 -- -82.50 -87.00 30.00 52 46 \w -122.00 -79.00 0.50 0.80 -- -82.50 -87.00 30.00 86 47 \w -150.00 -66.00 0.50 0.80 -- -82.50-135.00 -54.00 168 48 \w -146.00-120.00 0.50 0.80 -- -82.50 -87.00-120.00 52 49 \w -42.00 -17.00 0.50 0.80 -- -82.50 42.00 30.00 50 50 \w -59.00 -33.00 0.50 0.80 -- -82.50 59.00 30.00 52 51 \w -94.00 -18.00 0.50 0.20 -- -41.33 135.00 10.00 152 52 \w -80.00 -55.00 0.50 0.80 -- -82.50 135.00 10.00 50 53 \w -94.00 -18.00 0.50 0.20 -- -41.33 135.00-169.00 152 54 \w -94.00 -18.00 0.50 0.80 -- -82.50 135.00-169.00 152 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'XtaLAB Synergy, Dualflex, HyPix3000' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 -0.0261099000 _diffrn_orient_matrix_UB_12 -0.0602765000 _diffrn_orient_matrix_UB_13 -0.0698268000 _diffrn_orient_matrix_UB_21 -0.0980439000 _diffrn_orient_matrix_UB_22 -0.1784514000 _diffrn_orient_matrix_UB_23 0.0268070000 _diffrn_orient_matrix_UB_31 -0.2929758000 _diffrn_orient_matrix_UB_32 0.1247141000 _diffrn_orient_matrix_UB_33 0.0001072000 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0428 _diffrn_reflns_av_unetI/netI 0.0422 _diffrn_reflns_Laue_measured_fraction_full 0.986 _diffrn_reflns_Laue_measured_fraction_max 0.979 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_l_max 24 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_number 6817 _diffrn_reflns_point_group_measured_fraction_full 0.986 _diffrn_reflns_point_group_measured_fraction_max 0.979 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 68.144 _diffrn_reflns_theta_min 2.145 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'PhotonJet (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 3.863 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.39699 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour 'clear light colourless' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier light _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.492 _exptl_crystal_description needle _exptl_crystal_F_000 332 _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.1 _refine_diff_density_max 0.563 _refine_diff_density_min -0.595 _refine_diff_density_rms 0.094 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.049 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 174 _refine_ls_number_reflns 2590 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.049 _refine_ls_R_factor_all 0.0487 _refine_ls_R_factor_gt 0.0458 _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^)+(0.0851P)^2^+0.1783P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1233 _refine_ls_wR_factor_ref 0.1274 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2364 _reflns_number_total 2590 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d4sc02339k2.cif _cod_data_source_block sc-2brndi_1 _cod_database_code 1571735 _shelx_shelxl_version_number 2018/3 _chemical_oxdiff_formula 'C H N O Br' _chemical_oxdiff_usercomment @RT _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. ; _reflns_odcompleteness_completeness 99.03 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 66.97 _olex2_refinement_description ; 1.a Ternary CH refined with riding coordinates: C00D(H00D) 1.b Secondary CH2 refined with riding coordinates: C00C(H00A,H00B), C00E(H00C,H00E), C00G(H00I,H00J), C00H(H00K,H00L), C00J(H00P, H00Q) 1.c Aromatic/amide H refined with riding coordinates: C006(H006) 1.d Idealised Me refined as rotating group: C00F(H00F,H00G,H00H), C00I(H00M,H00N,H00O) ; _shelx_res_file ; TITL sc-2brndi_1_a.res in P-1 sc-2brndi_1.res created by SHELXL-2018/3 at 19:12:54 on 14-Sep-2021 REM Old TITL sc-2brndi_1_a.res in P-1 REM SHELXT solution in P-1 REM R1 0.138, Rweak 0.007, Alpha 0.073, Orientation as input REM Formula found by SHELXT: C15 Br N O2 CELL 1.54184 5.1363 7.0488 20.63 87.499 87.373 75.469 ZERR 1 0.0001 0.0002 0.0006 0.002 0.002 0.002 LATT 1 SFAC C H Br N O UNIT 30 36 2 2 4 L.S. 20 PLAN 2 CONF BOND $H list 4 fmap 2 53 acta MORE -1 REM REM REM WGHT 0.085100 0.178300 FVAR 0.65490 BR01 3 0.822647 0.921228 0.602491 11.00000 0.07140 0.04833 = 0.06460 -0.00429 -0.01075 -0.02590 O002 5 0.958417 0.725446 0.357503 11.00000 0.07888 0.07606 = 0.06161 0.00086 -0.00005 -0.04371 O003 5 0.468642 0.300363 0.311783 11.00000 0.10826 0.07401 = 0.05801 -0.00756 -0.00459 -0.04648 N004 4 0.705017 0.517071 0.333978 11.00000 0.05828 0.04987 = 0.05229 -0.00026 -0.00462 -0.01839 C005 1 0.542148 0.620404 0.577338 11.00000 0.04992 0.03954 = 0.05432 0.00236 -0.00948 -0.01135 C006 1 0.777954 0.744315 0.486814 11.00000 0.05655 0.04304 = 0.06017 0.00548 -0.00887 -0.02013 AFIX 43 H006 2 0.884105 0.827088 0.471532 11.00000 -1.20000 AFIX 0 C007 1 0.461312 0.499337 0.533409 11.00000 0.04888 0.03809 = 0.05327 0.00309 -0.00839 -0.01247 C008 1 0.698752 0.743865 0.553084 11.00000 0.05455 0.03741 = 0.05849 0.00034 -0.00902 -0.01506 C009 1 0.702570 0.626155 0.444528 11.00000 0.05302 0.04165 = 0.05431 0.00488 -0.00926 -0.01479 C00A 1 0.800647 0.630164 0.375805 11.00000 0.05531 0.04939 = 0.05770 0.00341 -0.00842 -0.01829 C00B 1 0.538609 0.391879 0.352394 11.00000 0.06197 0.04315 = 0.05372 -0.00129 -0.00666 -0.01818 C00C 1 0.799204 0.514521 0.265041 11.00000 0.05911 0.06145 = 0.05208 -0.00464 0.00165 -0.01649 AFIX 23 H00A 2 0.843664 0.380300 0.250976 11.00000 -1.20000 H00B 2 0.962627 0.560121 0.261545 11.00000 -1.20000 AFIX 0 C00D 1 0.593673 0.641026 0.219337 11.00000 0.07140 0.06137 = 0.05710 0.00068 -0.00507 -0.01354 AFIX 13 H00D 2 0.427862 0.596308 0.224886 11.00000 -1.20000 AFIX 0 C00E 1 0.524572 0.856363 0.234902 11.00000 0.08484 0.06237 = 0.08368 -0.00060 -0.01054 -0.01142 AFIX 23 H00C 2 0.499878 0.867796 0.281594 11.00000 -1.20000 H00E 2 0.675954 0.909557 0.221313 11.00000 -1.20000 AFIX 0 C00F 1 0.276426 0.978693 0.203458 11.00000 0.09012 0.07743 = 0.12012 0.01340 -0.01878 -0.00181 AFIX 137 H00F 2 0.295322 0.964714 0.157280 11.00000 -1.50000 H00G 2 0.253589 1.113872 0.213308 11.00000 -1.50000 H00H 2 0.122054 0.935536 0.219727 11.00000 -1.50000 AFIX 0 C00G 1 0.699710 0.602669 0.149365 11.00000 0.12485 0.10113 = 0.05484 -0.00179 -0.00586 0.00267 AFIX 23 H00I 2 0.888600 0.603078 0.146522 11.00000 -1.20000 H00J 2 0.603807 0.708545 0.121210 11.00000 -1.20000 AFIX 0 C00H 1 0.668137 0.403748 0.124555 11.00000 0.20207 0.10827 = 0.07829 -0.01045 -0.01361 0.03610 AFIX 23 H00K 2 0.755672 0.299777 0.154477 11.00000 -1.20000 H00L 2 0.478076 0.406878 0.126096 11.00000 -1.20000 AFIX 0 C00I 1 0.701997 0.173522 0.039420 11.00000 0.25928 0.15543 = 0.19564 -0.07859 -0.02666 -0.02450 AFIX 137 H00M 2 0.738825 0.158779 -0.006379 11.00000 -1.50000 H00N 2 0.514023 0.185054 0.048881 11.00000 -1.50000 H00O 2 0.806371 0.060963 0.062552 11.00000 -1.50000 AFIX 0 C00J 1 0.774830 0.353804 0.059983 11.00000 0.25934 0.17924 = 0.10606 -0.04716 -0.03019 0.02691 AFIX 23 H00P 2 0.969125 0.331621 0.059007 11.00000 -1.20000 H00Q 2 0.703389 0.461974 0.029878 11.00000 -1.20000 AFIX 0 HKLF 4 REM sc-2brndi_1_a.res in P-1 REM wR2 = 0.1274, GooF = S = 1.049, Restrained GooF = 1.049 for all data REM R1 = 0.0458 for 2364 Fo > 4sig(Fo) and 0.0487 for all 2590 data REM 174 parameters refined using 0 restraints END WGHT 0.0853 0.1780 REM Highest difference peak 0.563, deepest hole -0.595, 1-sigma level 0.094 Q1 1 0.6345 0.9451 0.6038 11.00000 0.05 0.56 Q2 1 0.8341 0.4548 0.1098 11.00000 0.05 0.54 ; _shelx_res_checksum 71486 _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 1.768 _oxdiff_exptl_absorpt_empirical_full_min 0.475 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, -z' 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 Br01 Br 0.82265(7) 0.92123(4) 0.60249(2) 0.05915(18) Uani 1 1 d . . . . . O002 O 0.9584(5) 0.7254(4) 0.35750(13) 0.0680(7) Uani 1 1 d . . . . . O003 O 0.4686(7) 0.3004(4) 0.31178(13) 0.0756(7) Uani 1 1 d . . . . . N004 N 0.7050(5) 0.5171(4) 0.33398(13) 0.0526(6) Uani 1 1 d . . . . . C005 C 0.5421(6) 0.6204(4) 0.57734(16) 0.0478(6) Uani 1 1 d . . . . . C006 C 0.7780(6) 0.7443(5) 0.48681(16) 0.0519(7) Uani 1 1 d . . . . . H006 H 0.884105 0.827088 0.471532 0.062 Uiso 1 1 calc R U . . . C007 C 0.4613(6) 0.4993(4) 0.53341(15) 0.0464(6) Uani 1 1 d . . . . . C008 C 0.6988(6) 0.7439(4) 0.55308(16) 0.0493(6) Uani 1 1 d . . . . . C009 C 0.7026(6) 0.6262(5) 0.44453(16) 0.0491(7) Uani 1 1 d . . . . . C00A C 0.8006(6) 0.6302(5) 0.37581(17) 0.0532(7) Uani 1 1 d . . . . . C00B C 0.5386(7) 0.3919(5) 0.35239(16) 0.0519(7) Uani 1 1 d . . . . . C00C C 0.7992(7) 0.5145(5) 0.26504(16) 0.0573(7) Uani 1 1 d . . . . . H00A H 0.843664 0.380300 0.250976 0.069 Uiso 1 1 calc R U . . . H00B H 0.962627 0.560121 0.261545 0.069 Uiso 1 1 calc R U . . . C00D C 0.5937(8) 0.6410(6) 0.21934(17) 0.0638(8) Uani 1 1 d . . . . . H00D H 0.427862 0.596308 0.224886 0.077 Uiso 1 1 calc R U . . . C00E C 0.5246(9) 0.8564(6) 0.2349(2) 0.0780(11) Uani 1 1 d . . . . . H00C H 0.499878 0.867796 0.281594 0.094 Uiso 1 1 calc R U . . . H00E H 0.675954 0.909557 0.221313 0.094 Uiso 1 1 calc R U . . . C00F C 0.2764(10) 0.9787(8) 0.2035(3) 0.0993(16) Uani 1 1 d . . . . . H00F H 0.295322 0.964714 0.157280 0.149 Uiso 1 1 calc R U . . . H00G H 0.253589 1.113872 0.213308 0.149 Uiso 1 1 calc R U . . . H00H H 0.122054 0.935536 0.219727 0.149 Uiso 1 1 calc R U . . . C00G C 0.6997(13) 0.6027(9) 0.1494(2) 0.0991(17) Uani 1 1 d . . . . . H00I H 0.888600 0.603078 0.146522 0.119 Uiso 1 1 calc R U . . . H00J H 0.603807 0.708545 0.121210 0.119 Uiso 1 1 calc R U . . . C00H C 0.6681(19) 0.4037(11) 0.1246(3) 0.142(3) Uani 1 1 d . . . . . H00K H 0.755672 0.299777 0.154477 0.171 Uiso 1 1 calc R U . . . H00L H 0.478076 0.406878 0.126096 0.171 Uiso 1 1 calc R U . . . C00I C 0.702(3) 0.1735(16) 0.0394(6) 0.206(6) Uani 1 1 d . . . . . H00M H 0.738825 0.158779 -0.006379 0.308 Uiso 1 1 calc R U . . . H00N H 0.514023 0.185054 0.048881 0.308 Uiso 1 1 calc R U . . . H00O H 0.806371 0.060963 0.062552 0.308 Uiso 1 1 calc R U . . . C00J C 0.775(3) 0.3538(17) 0.0600(4) 0.194(5) Uani 1 1 d . . . . . H00P H 0.969125 0.331621 0.059007 0.233 Uiso 1 1 calc R U . . . H00Q H 0.703389 0.461974 0.029878 0.233 Uiso 1 1 calc R U . . . 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 Br01 0.0714(3) 0.0483(2) 0.0646(3) -0.00429(16) -0.01075(17) -0.02590(17) O002 0.0789(16) 0.0761(17) 0.0616(14) 0.0009(12) -0.0001(12) -0.0437(13) O003 0.108(2) 0.0740(17) 0.0580(14) -0.0076(13) -0.0046(13) -0.0465(16) N004 0.0583(14) 0.0499(14) 0.0523(14) -0.0003(11) -0.0046(11) -0.0184(11) C005 0.0499(15) 0.0395(14) 0.0543(16) 0.0024(12) -0.0095(12) -0.0113(12) C006 0.0565(16) 0.0430(15) 0.0602(18) 0.0055(13) -0.0089(13) -0.0201(13) C007 0.0489(14) 0.0381(13) 0.0533(16) 0.0031(12) -0.0084(12) -0.0125(11) C008 0.0545(15) 0.0374(13) 0.0585(17) 0.0003(12) -0.0090(13) -0.0151(12) C009 0.0530(15) 0.0417(14) 0.0543(16) 0.0049(13) -0.0093(12) -0.0148(12) C00A 0.0553(16) 0.0494(16) 0.0577(18) 0.0034(14) -0.0084(13) -0.0183(13) C00B 0.0620(17) 0.0431(15) 0.0537(17) -0.0013(13) -0.0067(13) -0.0182(13) C00C 0.0591(17) 0.0615(19) 0.0521(17) -0.0046(15) 0.0017(13) -0.0165(15) C00D 0.071(2) 0.061(2) 0.0571(19) 0.0007(16) -0.0051(15) -0.0135(16) C00E 0.085(3) 0.062(2) 0.084(3) -0.001(2) -0.011(2) -0.0114(19) C00F 0.090(3) 0.077(3) 0.120(4) 0.013(3) -0.019(3) -0.002(2) C00G 0.125(4) 0.101(4) 0.055(2) -0.002(2) -0.006(2) 0.003(3) C00H 0.202(8) 0.108(5) 0.078(3) -0.010(3) -0.014(4) 0.036(5) C00I 0.259(14) 0.155(10) 0.196(11) -0.079(9) -0.027(10) -0.025(9) C00J 0.259(13) 0.179(10) 0.106(6) -0.047(6) -0.030(6) 0.027(9) 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 C00A N004 C00B 125.2(3) . . ? C00A N004 C00C 118.3(3) . . ? C00B N004 C00C 116.3(3) . . ? C007 C005 C00B 119.2(3) . 2_666 ? C008 C005 C007 118.1(3) . . ? C008 C005 C00B 122.7(3) . 2_666 ? C008 C006 H006 119.2 . . ? C009 C006 H006 119.2 . . ? C009 C006 C008 121.5(3) . . ? C005 C007 C007 121.6(4) . 2_666 ? C005 C007 C009 120.3(3) . 2_666 ? C009 C007 C007 118.1(4) 2_666 2_666 ? C005 C008 Br01 125.2(3) . . ? C005 C008 C006 120.4(3) . . ? C006 C008 Br01 114.3(2) . . ? C006 C009 C007 120.2(3) . 2_666 ? C006 C009 C00A 118.5(3) . . ? C007 C009 C00A 121.3(3) 2_666 . ? O002 C00A N004 121.9(3) . . ? O002 C00A C009 121.8(3) . . ? N004 C00A C009 116.3(3) . . ? O003 C00B N004 119.3(3) . . ? O003 C00B C005 123.2(3) . 2_666 ? N004 C00B C005 117.5(3) . 2_666 ? N004 C00C H00A 108.8 . . ? N004 C00C H00B 108.8 . . ? N004 C00C C00D 114.0(3) . . ? H00A C00C H00B 107.7 . . ? C00D C00C H00A 108.8 . . ? C00D C00C H00B 108.8 . . ? C00C C00D H00D 107.5 . . ? C00E C00D C00C 112.7(3) . . ? C00E C00D H00D 107.5 . . ? C00E C00D C00G 112.9(4) . . ? C00G C00D C00C 108.4(3) . . ? C00G C00D H00D 107.5 . . ? C00D C00E H00C 108.6 . . ? C00D C00E H00E 108.6 . . ? H00C C00E H00E 107.6 . . ? C00F C00E C00D 114.7(4) . . ? C00F C00E H00C 108.6 . . ? C00F C00E H00E 108.6 . . ? C00E C00F H00F 109.5 . . ? C00E C00F H00G 109.5 . . ? C00E C00F H00H 109.5 . . ? H00F C00F H00G 109.5 . . ? H00F C00F H00H 109.5 . . ? H00G C00F H00H 109.5 . . ? C00D C00G H00I 108.9 . . ? C00D C00G H00J 108.9 . . ? C00D C00G C00H 113.2(5) . . ? H00I C00G H00J 107.8 . . ? C00H C00G H00I 108.9 . . ? C00H C00G H00J 108.9 . . ? C00G C00H H00K 108.2 . . ? C00G C00H H00L 108.2 . . ? H00K C00H H00L 107.4 . . ? C00J C00H C00G 116.2(9) . . ? C00J C00H H00K 108.2 . . ? C00J C00H H00L 108.2 . . ? H00M C00I H00N 109.5 . . ? H00M C00I H00O 109.5 . . ? H00N C00I H00O 109.5 . . ? C00J C00I H00M 109.5 . . ? C00J C00I H00N 109.5 . . ? C00J C00I H00O 109.5 . . ? C00H C00J C00I 110.6(12) . . ? C00H C00J H00P 109.5 . . ? C00H C00J H00Q 109.5 . . ? C00I C00J H00P 109.5 . . ? C00I C00J H00Q 109.5 . . ? H00P C00J H00Q 108.1 . . ? 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 Br01 C008 1.891(3) . ? O002 C00A 1.214(4) . ? O003 C00B 1.199(4) . ? N004 C00A 1.384(4) . ? N004 C00B 1.405(4) . ? N004 C00C 1.480(4) . ? C005 C007 1.415(5) . ? C005 C008 1.390(4) . ? C005 C00B 1.494(5) 2_666 ? C006 H006 0.9300 . ? C006 C008 1.409(5) . ? C006 C009 1.364(5) . ? C007 C007 1.417(6) 2_666 ? C007 C009 1.415(4) 2_666 ? C009 C00A 1.484(5) . ? C00C H00A 0.9700 . ? C00C H00B 0.9700 . ? C00C C00D 1.531(5) . ? C00D H00D 0.9800 . ? C00D C00E 1.515(6) . ? C00D C00G 1.530(6) . ? C00E H00C 0.9700 . ? C00E H00E 0.9700 . ? C00E C00F 1.505(6) . ? C00F H00F 0.9600 . ? C00F H00G 0.9600 . ? C00F H00H 0.9600 . ? C00G H00I 0.9700 . ? C00G H00J 0.9700 . ? C00G C00H 1.562(11) . ? C00H H00K 0.9700 . ? C00H H00L 0.9700 . ? C00H C00J 1.441(11) . ? C00I H00M 0.9600 . ? C00I H00N 0.9600 . ? C00I H00O 0.9600 . ? C00I C00J 1.495(16) . ? C00J H00P 0.9700 . ? C00J H00Q 0.9700 . ? 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 N004 C00C C00D C00E 62.1(4) . . . . ? N004 C00C C00D C00G -172.2(4) . . . . ? C006 C009 C00A O002 4.8(5) . . . . ? C006 C009 C00A N004 -176.1(3) . . . . ? C007 C005 C008 Br01 178.6(2) . . . . ? C007 C005 C008 C006 -1.2(4) . . . . ? C007 C009 C00A O002 -174.0(3) 2_666 . . . ? C007 C009 C00A N004 5.1(4) 2_666 . . . ? C008 C005 C007 C007 0.7(5) . . . 2_666 ? C008 C005 C007 C009 -178.8(3) . . . 2_666 ? C008 C006 C009 C007 0.7(5) . . . 2_666 ? C008 C006 C009 C00A -178.1(3) . . . . ? C009 C006 C008 Br01 -179.3(2) . . . . ? C009 C006 C008 C005 0.6(5) . . . . ? C00A N004 C00B O003 -179.8(3) . . . . ? C00A N004 C00B C005 0.1(5) . . . 2_666 ? C00A N004 C00C C00D -102.8(4) . . . . ? C00B N004 C00A O002 175.0(3) . . . . ? C00B N004 C00A C009 -4.2(4) . . . . ? C00B N004 C00C C00D 81.6(4) . . . . ? C00B C005 C007 C007 -178.1(3) 2_666 . . 2_666 ? C00B C005 C007 C009 2.4(4) 2_666 . . 2_666 ? C00B C005 C008 Br01 -2.6(4) 2_666 . . . ? C00B C005 C008 C006 177.5(3) 2_666 . . . ? C00C N004 C00A O002 -0.2(5) . . . . ? C00C N004 C00A C009 -179.4(3) . . . . ? C00C N004 C00B O003 -4.5(5) . . . . ? C00C N004 C00B C005 175.4(3) . . . 2_666 ? C00C C00D C00E C00F -165.2(4) . . . . ? C00C C00D C00G C00H 76.4(6) . . . . ? C00D C00G C00H C00J -177.3(7) . . . . ? C00E C00D C00G C00H -158.0(5) . . . . ? C00G C00D C00E C00F 71.6(6) . . . . ? C00G C00H C00J C00I -173.1(9) . . . . ?