#------------------------------------------------------------------------------ #$Date: 2020-07-06 06:43:50 +0300 (Mon, 06 Jul 2020) $ #$Revision: 253975 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/15/75/7157533.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_7157533 loop_ _publ_author_name 'Shi, Yaqi' 'Yang, Fan' 'Wu, Yangjie' _publ_section_title ; Palladium-catalyzed C8-H alkoxycarbonylation of 1-naphthylamines with alkyl chloroformates. ; _journal_issue 24 _journal_name_full 'Organic & biomolecular chemistry' _journal_page_first 4628 _journal_page_last 4637 _journal_paper_doi 10.1039/d0ob00586j _journal_volume 18 _journal_year 2020 _chemical_formula_moiety 'C20 H17 Br N2 O3' _chemical_formula_sum 'C20 H17 Br N2 O3' _chemical_formula_weight 413.26 _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 mixed _atom_sites_solution_primary iterative _audit_creation_date 2019-07-11 _audit_creation_method ; Olex2 1.2 (compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) ; _audit_update_record ; 2019-09-26 deposited with the CCDC. 2020-06-01 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 100.731(7) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 16.6385(13) _cell_length_b 14.3268(8) _cell_length_c 7.7041(5) _cell_measurement_reflns_used 1643 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 68.5280 _cell_measurement_theta_min 6.1570 _cell_volume 1804.4(2) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01) ; _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 ; Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008; Palatinus et al., 2012) ; _diffrn_ambient_temperature 293(2) _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 16.2312 _diffrn_detector_type Eos _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -55.00 38.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - -33.5000 0.0000 90.0000 93 #__ type_ start__ end____ width___ exp.time_ 2 omega -92.00 -66.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - -33.5000 0.0000 90.0000 26 #__ type_ start__ end____ width___ exp.time_ 3 omega -18.00 17.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - -33.5000 37.0000 120.0000 35 #__ type_ start__ end____ width___ exp.time_ 4 omega -4.00 66.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 36.4734 -99.0000 -180.0000 70 #__ type_ start__ end____ width___ exp.time_ 5 omega 67.00 109.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 36.4734 178.0000 -180.0000 42 #__ type_ start__ end____ width___ exp.time_ 6 omega 27.00 53.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 36.4734 57.0000 -150.0000 26 #__ type_ start__ end____ width___ exp.time_ 7 omega 72.00 98.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 36.4734 57.0000 -150.0000 26 #__ type_ start__ end____ width___ exp.time_ 8 omega 80.00 106.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 36.4734 178.0000 -60.0000 26 #__ type_ start__ end____ width___ exp.time_ 9 omega 63.00 90.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 36.4734 178.0000 -30.0000 27 #__ type_ start__ end____ width___ exp.time_ 10 omega 127.00 157.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 45.0000 0.0000 30 #__ type_ start__ end____ width___ exp.time_ 11 omega 93.00 172.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 77.0000 -120.0000 79 #__ type_ start__ end____ width___ exp.time_ 12 omega 50.00 120.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 -61.0000 -150.0000 70 #__ type_ start__ end____ width___ exp.time_ 13 omega 42.00 81.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 -30.0000 0.0000 39 #__ type_ start__ end____ width___ exp.time_ 14 omega 42.00 100.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 -94.0000 -180.0000 58 #__ type_ start__ end____ width___ exp.time_ 15 omega 65.00 176.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 15.0000 -180.0000 111 #__ type_ start__ end____ width___ exp.time_ 16 omega 48.00 90.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 -30.0000 150.0000 42 #__ type_ start__ end____ width___ exp.time_ 17 omega 57.00 112.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 -111.0000 90.0000 55 #__ type_ start__ end____ width___ exp.time_ 18 omega 42.00 96.00 1.0000 1.0000 omega____ theta____ kappa____ phi______ frames - 108.0000 -94.0000 0.0000 54 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'Xcalibur, Eos, Gemini' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 0.0138872000 _diffrn_orient_matrix_UB_12 -0.0997878000 _diffrn_orient_matrix_UB_13 0.0739803000 _diffrn_orient_matrix_UB_21 -0.0050023000 _diffrn_orient_matrix_UB_22 0.0363085000 _diffrn_orient_matrix_UB_23 0.1857714000 _diffrn_orient_matrix_UB_31 -0.0931387000 _diffrn_orient_matrix_UB_32 -0.0168803000 _diffrn_orient_matrix_UB_33 -0.0372066000 _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0468 _diffrn_reflns_av_unetI/netI 0.0652 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.999 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_h_min -19 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_limit_l_min -8 _diffrn_reflns_number 6920 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.999 _diffrn_reflns_theta_full 67.080 _diffrn_reflns_theta_max 67.080 _diffrn_reflns_theta_min 4.103 _diffrn_source 'Enhance (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 3.296 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.92381 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.521 _exptl_crystal_description block _exptl_crystal_F_000 840 _exptl_crystal_size_max 0.19 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.11 _refine_diff_density_max 0.353 _refine_diff_density_min -0.433 _refine_diff_density_rms 0.070 _refine_ls_extinction_coef 0.0037(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method 'SHELXL-2014/7 (Sheldrick 2014' _refine_ls_goodness_of_fit_ref 1.053 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 242 _refine_ls_number_reflns 3221 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.053 _refine_ls_R_factor_all 0.0755 _refine_ls_R_factor_gt 0.0486 _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^)+(0.0455P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1062 _refine_ls_wR_factor_ref 0.1265 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2250 _reflns_number_total 3221 _reflns_threshold_expression 'I > 2\s(I)' _iucr_refine_instructions_details ; 201907185.res created by SHELXL-2014/7 TITL CF solution in P21/c CELL 1.54184 16.638473 14.326774 7.70407 90 100.7314 90 ZERR 4 0.001341 0.000797 0.000501 0 0.0072 0 LATT 1 SYMM -X,0.5+Y,0.5-Z SFAC C H Br N O UNIT 80 68 4 8 12 L.S. 4 0 0 PLAN 20 SIZE 0.11 0.14 0.19 MPLA C1 C2 C3 C4 C5 C6 C7 C8 C9 C10 MPLA C12 C13 C14 C15 C16 N2 HTAB N1 O2 BOND $H CONF fmap 2 acta REM REM REM WGHT 0.045500 EXTI 0.003695 FVAR 5.60537 BR1 3 0.390231 0.942260 0.368650 11.00000 0.10557 0.04704 = 0.06521 -0.00429 0.03276 -0.02651 C1 1 0.335877 0.829362 0.407636 11.00000 0.05887 0.03721 = 0.03991 -0.00194 0.00839 -0.01269 C2 1 0.260496 0.835791 0.450656 11.00000 0.06141 0.03444 = 0.04723 -0.00719 0.00975 0.00256 AFIX 43 H2 2 0.238122 0.893873 0.467195 11.00000 -1.20000 AFIX 0 C3 1 0.217290 0.754858 0.469634 11.00000 0.04680 0.04275 = 0.05051 -0.00146 0.00982 -0.00010 AFIX 43 H3 2 0.166441 0.759292 0.502684 11.00000 -1.20000 AFIX 0 C4 1 0.247495 0.669002 0.441056 11.00000 0.03849 0.03575 = 0.04061 0.00226 0.00353 -0.00131 C5 1 0.327637 0.659756 0.400022 11.00000 0.03908 0.03783 = 0.02890 0.00258 0.00037 -0.00054 C6 1 0.373620 0.742946 0.386771 11.00000 0.04420 0.04447 = 0.03181 0.00065 0.00387 -0.00551 C7 1 0.454429 0.734831 0.353686 11.00000 0.04453 0.06036 = 0.05698 -0.00555 0.01111 -0.01316 AFIX 43 H7 2 0.484919 0.788582 0.346083 11.00000 -1.20000 AFIX 0 C8 1 0.488013 0.650558 0.332987 11.00000 0.03286 0.08564 = 0.06345 -0.00082 0.01418 -0.00278 AFIX 43 H8 2 0.541649 0.646932 0.314894 11.00000 -1.20000 AFIX 0 C9 1 0.442564 0.568718 0.338615 11.00000 0.04458 0.06082 = 0.05567 -0.00005 0.00963 0.01493 AFIX 43 H9 2 0.465863 0.511381 0.320441 11.00000 -1.20000 AFIX 0 C10 1 0.363835 0.571831 0.370671 11.00000 0.04421 0.03854 = 0.03706 -0.00049 0.00240 0.00411 C11 1 0.127703 0.573328 0.337409 11.00000 0.03850 0.04804 = 0.04560 0.00305 0.00888 -0.00117 C12 1 0.084872 0.484045 0.367839 11.00000 0.03581 0.04506 = 0.05356 -0.00425 0.01600 -0.00298 C13 1 0.015061 0.458546 0.253331 11.00000 0.05099 0.07159 = 0.06041 -0.00591 0.00148 -0.00888 AFIX 43 H13 2 -0.007650 0.497099 0.159879 11.00000 -1.20000 AFIX 0 C14 1 -0.020907 0.373447 0.280656 11.00000 0.05490 0.07389 = 0.09943 -0.03170 0.01109 -0.02192 AFIX 43 H14 2 -0.067965 0.353786 0.204594 11.00000 -1.20000 AFIX 0 C15 1 0.013494 0.319339 0.419788 11.00000 0.07063 0.04985 = 0.10107 -0.01527 0.03227 -0.01982 AFIX 43 H15 2 -0.008996 0.261864 0.440254 11.00000 -1.20000 AFIX 0 C16 1 0.082236 0.351984 0.528876 11.00000 0.06833 0.05220 = 0.07708 -0.00102 0.01795 -0.01137 AFIX 43 H16 2 0.104464 0.315581 0.625933 11.00000 -1.20000 AFIX 0 C17 1 0.321111 0.479815 0.362650 11.00000 0.04768 0.04087 = 0.04331 -0.00040 0.00776 0.00989 C18 1 0.249626 0.368786 0.157491 11.00000 0.07746 0.04511 = 0.06651 -0.00588 0.01794 -0.01180 AFIX 13 H18 2 0.221602 0.348559 0.252194 11.00000 -1.20000 AFIX 0 C19 1 0.317668 0.302465 0.144096 11.00000 0.12051 0.06015 = 0.11579 -0.02403 0.03846 0.01008 AFIX 137 H19A 2 0.344445 0.321714 0.049899 11.00000 -1.50000 H19B 2 0.295836 0.240777 0.120429 11.00000 -1.50000 H19C 2 0.356379 0.302351 0.253366 11.00000 -1.50000 AFIX 0 C20 1 0.188641 0.380902 -0.009461 11.00000 0.11053 0.08703 = 0.07729 -0.01197 -0.00833 -0.03228 AFIX 137 H20A 2 0.149735 0.427982 0.007247 11.00000 -1.50000 H20B 2 0.160680 0.322933 -0.040356 11.00000 -1.50000 H20C 2 0.216286 0.399583 -0.102650 11.00000 -1.50000 AFIX 0 N1 4 0.198304 0.588733 0.452282 11.00000 0.04009 0.03659 = 0.04854 0.00537 0.00650 -0.00180 H1 2 0.214223 0.550842 0.525963 11.00000 0.05129 N2 4 0.119283 0.431428 0.506291 11.00000 0.05696 0.04214 = 0.06202 0.00233 0.01399 -0.00821 O1 5 0.099494 0.625241 0.215797 11.00000 0.06280 0.06639 = 0.07086 0.02233 -0.00646 -0.00791 O2 5 0.324352 0.427031 0.484399 11.00000 0.08527 0.04563 = 0.05568 0.01351 0.00332 0.00056 O3 5 0.284133 0.461993 0.197678 11.00000 0.07168 0.04031 = 0.04474 -0.00181 0.00726 -0.00418 HKLF 4 REM CF solution in P21/c REM R1 = 0.0486 for 2250 Fo > 4sig(Fo) and 0.0755 for all 3221 data REM 242 parameters refined using 0 restraints END WGHT 0.0455 0.0000 REM Highest difference peak 0.353, deepest hole -0.433, 1-sigma level 0.070 Q1 1 0.4234 0.8954 0.3515 11.00000 0.05 0.35 Q2 1 0.4042 0.9280 0.2439 11.00000 0.05 0.32 Q3 1 0.3780 0.9612 0.5040 11.00000 0.05 0.30 Q4 1 0.1659 0.4417 0.5978 11.00000 0.05 0.29 Q5 1 0.3455 0.9107 0.2185 11.00000 0.05 0.29 Q6 1 0.2458 0.6800 0.6705 11.00000 0.05 0.26 Q7 1 0.4668 0.9500 0.4723 11.00000 0.05 0.25 Q8 1 0.4480 0.6035 0.1497 11.00000 0.05 0.24 Q9 1 -0.0677 0.4445 0.0356 11.00000 0.05 0.24 Q10 1 0.6013 0.5446 0.3180 11.00000 0.05 0.23 Q11 1 0.3399 0.5559 0.5954 11.00000 0.05 0.23 Q12 1 0.2646 0.8377 0.3247 11.00000 0.05 0.22 Q13 1 0.3263 0.7732 0.1625 11.00000 0.05 0.22 Q14 1 0.2990 0.5991 0.6265 11.00000 0.05 0.21 Q15 1 0.2448 0.5367 0.6180 11.00000 0.05 0.21 Q16 1 0.4333 0.5804 0.5028 11.00000 0.05 0.21 Q17 1 0.3483 0.8511 0.5962 11.00000 0.05 0.21 Q18 1 0.3345 0.8980 0.6290 11.00000 0.05 0.21 Q19 1 0.4163 0.6181 0.6169 11.00000 0.05 0.20 Q20 1 -0.0211 0.3827 0.0028 11.00000 0.05 0.20 REM The information below was added by Olex2. REM REM R1 = 0.0486 for 2250 Fo > 4sig(Fo) and 0.0755 for all 7135 data REM n/a parameters refined using n/a restraints REM Highest difference peak 0.35, deepest hole -0.43 REM Mean Shift 0, Max Shift 0.001. REM +++ Tabular Listing of Refinement Information +++ REM R1_all = 0.0755 REM R1_gt = 0.0486 REM wR_ref = 0.1265 REM GOOF = 1.053 REM Shift_max = 0.001 REM Shift_mean = 0 REM Reflections_all = 7135 REM Reflections_gt = 2250 REM Parameters = n/a REM Hole = -0.43 REM Peak = 0.35 REM Flack = n/a ; _cod_data_source_file d0ob00586j2.cif _cod_data_source_block 201907185 _cod_depositor_comments 'Adding full bibliography for 7157533.cif.' _cod_original_cell_volume 1804.3(2) _cod_database_code 7157533 _shelx_shelxl_version_number 2014/7 _chemical_oxdiff_formula C20H20O6N4K1 _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 0.713 _shelx_estimated_absorpt_t_min 0.573 _reflns_odcompleteness_completeness 99.91 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 66.97 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups At 1.5 times of: All C(H,H,H) groups 2.a Ternary CH refined with riding coordinates: C18(H18) 2.b Aromatic/amide H refined with riding coordinates: C2(H2), C3(H3), C7(H7), C8(H8), C9(H9), C13(H13), C14(H14), C15(H15), C16(H16) 2.c Idealised Me refined as rotating group: C19(H19A,H19B,H19C), C20(H20A,H20B,H20C) ; _olex2_submission_special_instructions 'No special instructions were received' 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 0.39023(4) 0.94226(4) 0.36865(7) 0.0704(3) Uani 1 1 d . . . . . C1 C 0.3359(3) 0.8294(3) 0.4076(5) 0.0454(10) Uani 1 1 d . . . . . C2 C 0.2605(3) 0.8358(3) 0.4507(5) 0.0477(10) Uani 1 1 d . . . . . H2 H 0.2381 0.8939 0.4672 0.057 Uiso 1 1 calc R . . . . C3 C 0.2173(2) 0.7549(3) 0.4696(5) 0.0466(10) Uani 1 1 d . . . . . H3 H 0.1664 0.7593 0.5027 0.056 Uiso 1 1 calc R . . . . C4 C 0.2475(2) 0.6690(3) 0.4411(5) 0.0388(9) Uani 1 1 d . . . . . C5 C 0.3276(2) 0.6598(3) 0.4000(4) 0.0360(8) Uani 1 1 d . . . . . C6 C 0.3736(2) 0.7429(3) 0.3868(5) 0.0406(9) Uani 1 1 d . . . . . C7 C 0.4544(2) 0.7348(3) 0.3537(6) 0.0537(11) Uani 1 1 d . . . . . H7 H 0.4849 0.7886 0.3461 0.064 Uiso 1 1 calc R . . . . C8 C 0.4880(2) 0.6506(4) 0.3330(6) 0.0600(13) Uani 1 1 d . . . . . H8 H 0.5416 0.6469 0.3149 0.072 Uiso 1 1 calc R . . . . C9 C 0.4426(3) 0.5687(3) 0.3386(6) 0.0537(11) Uani 1 1 d . . . . . H9 H 0.4659 0.5114 0.3204 0.064 Uiso 1 1 calc R . . . . C10 C 0.3638(2) 0.5718(3) 0.3707(5) 0.0406(9) Uani 1 1 d . . . . . C11 C 0.1277(2) 0.5733(3) 0.3374(5) 0.0439(10) Uani 1 1 d . . . . . C12 C 0.0849(2) 0.4840(3) 0.3678(5) 0.0438(10) Uani 1 1 d . . . . . C13 C 0.0151(3) 0.4585(3) 0.2533(6) 0.0621(13) Uani 1 1 d . . . . . H13 H -0.0076 0.4971 0.1599 0.075 Uiso 1 1 calc R . . . . C14 C -0.0209(3) 0.3734(4) 0.2807(8) 0.0765(16) Uani 1 1 d . . . . . H14 H -0.0680 0.3538 0.2046 0.092 Uiso 1 1 calc R . . . . C15 C 0.0135(3) 0.3193(4) 0.4198(8) 0.0718(15) Uani 1 1 d . . . . . H15 H -0.0090 0.2619 0.4403 0.086 Uiso 1 1 calc R . . . . C16 C 0.0822(3) 0.3520(3) 0.5289(7) 0.0653(13) Uani 1 1 d . . . . . H16 H 0.1045 0.3156 0.6259 0.078 Uiso 1 1 calc R . . . . C17 C 0.3211(2) 0.4798(3) 0.3626(5) 0.0440(9) Uani 1 1 d . . . . . C18 C 0.2496(3) 0.3688(3) 0.1575(7) 0.0624(13) Uani 1 1 d . . . . . H18 H 0.2216 0.3486 0.2522 0.075 Uiso 1 1 calc R . . . . C19 C 0.3177(4) 0.3025(4) 0.1441(9) 0.097(2) Uani 1 1 d . . . . . H19A H 0.3444 0.3217 0.0499 0.145 Uiso 1 1 calc GR . . . . H19B H 0.2958 0.2408 0.1204 0.145 Uiso 1 1 calc GR . . . . H19C H 0.3564 0.3024 0.2534 0.145 Uiso 1 1 calc GR . . . . C20 C 0.1886(4) 0.3809(4) -0.0095(7) 0.0949(19) Uani 1 1 d . . . . . H20A H 0.1497 0.4280 0.0072 0.142 Uiso 1 1 calc GR . . . . H20B H 0.1607 0.3229 -0.0404 0.142 Uiso 1 1 calc GR . . . . H20C H 0.2163 0.3996 -0.1026 0.142 Uiso 1 1 calc GR . . . . N1 N 0.1983(2) 0.5887(2) 0.4523(5) 0.0420(8) Uani 1 1 d . . . . . H1 H 0.214(3) 0.551(3) 0.526(6) 0.051(14) Uiso 1 1 d . . . . . N2 N 0.1193(2) 0.4314(2) 0.5063(5) 0.0533(9) Uani 1 1 d . . . . . O1 O 0.09949(19) 0.6252(2) 0.2158(4) 0.0691(10) Uani 1 1 d . . . . . O2 O 0.3244(2) 0.4270(2) 0.4844(4) 0.0635(9) Uani 1 1 d . . . . . O3 O 0.28413(18) 0.46199(19) 0.1977(4) 0.0527(8) Uani 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 Br1 0.1056(5) 0.0470(3) 0.0652(4) -0.0043(2) 0.0328(3) -0.0265(3) C1 0.059(3) 0.037(2) 0.040(2) -0.0019(18) 0.0084(19) -0.013(2) C2 0.061(3) 0.034(2) 0.047(2) -0.0072(18) 0.010(2) 0.003(2) C3 0.047(2) 0.043(2) 0.051(2) -0.0015(19) 0.0098(19) -0.0001(19) C4 0.038(2) 0.036(2) 0.041(2) 0.0023(17) 0.0035(17) -0.0013(17) C5 0.039(2) 0.038(2) 0.0289(18) 0.0026(16) 0.0004(15) -0.0005(17) C6 0.044(2) 0.044(2) 0.0318(18) 0.0007(17) 0.0039(16) -0.0055(18) C7 0.045(2) 0.060(3) 0.057(3) -0.006(2) 0.011(2) -0.013(2) C8 0.033(2) 0.086(4) 0.063(3) -0.001(3) 0.014(2) -0.003(2) C9 0.045(2) 0.061(3) 0.056(3) 0.000(2) 0.010(2) 0.015(2) C10 0.044(2) 0.039(2) 0.037(2) -0.0005(16) 0.0024(17) 0.0041(18) C11 0.039(2) 0.048(3) 0.046(2) 0.0031(19) 0.0089(18) -0.0012(19) C12 0.036(2) 0.045(2) 0.054(2) -0.0043(19) 0.0160(18) -0.0030(18) C13 0.051(3) 0.072(3) 0.060(3) -0.006(3) 0.001(2) -0.009(2) C14 0.055(3) 0.074(4) 0.099(5) -0.032(3) 0.011(3) -0.022(3) C15 0.071(3) 0.050(3) 0.101(4) -0.015(3) 0.032(3) -0.020(3) C16 0.068(3) 0.052(3) 0.077(3) -0.001(2) 0.018(3) -0.011(2) C17 0.048(2) 0.041(2) 0.043(2) -0.0004(19) 0.0078(19) 0.0099(19) C18 0.077(3) 0.045(3) 0.067(3) -0.006(2) 0.018(3) -0.012(2) C19 0.121(5) 0.060(4) 0.116(5) -0.024(3) 0.038(4) 0.010(3) C20 0.111(5) 0.087(4) 0.077(4) -0.012(3) -0.008(4) -0.032(4) N1 0.0401(19) 0.0366(19) 0.049(2) 0.0054(16) 0.0065(16) -0.0018(15) N2 0.057(2) 0.042(2) 0.062(2) 0.0023(17) 0.0140(18) -0.0082(17) O1 0.063(2) 0.066(2) 0.071(2) 0.0223(18) -0.0065(16) -0.0079(17) O2 0.085(2) 0.0456(19) 0.0557(19) 0.0135(15) 0.0033(17) 0.0006(16) O3 0.072(2) 0.0403(17) 0.0447(16) -0.0018(13) 0.0073(15) -0.0042(15) 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 C2 C1 Br1 117.9(3) . . ? C2 C1 C6 122.5(4) . . ? C6 C1 Br1 119.5(3) . . ? C1 C2 H2 120.3 . . ? C1 C2 C3 119.3(4) . . ? C3 C2 H2 120.4 . . ? C2 C3 H3 119.2 . . ? C4 C3 C2 121.6(4) . . ? C4 C3 H3 119.2 . . ? C3 C4 C5 120.4(4) . . ? C3 C4 N1 119.1(3) . . ? N1 C4 C5 120.5(3) . . ? C6 C5 C4 118.1(3) . . ? C6 C5 C10 118.4(3) . . ? C10 C5 C4 123.5(3) . . ? C1 C6 C5 117.9(3) . . ? C1 C6 C7 123.3(4) . . ? C7 C6 C5 118.8(4) . . ? C6 C7 H7 119.3 . . ? C8 C7 C6 121.4(4) . . ? C8 C7 H7 119.3 . . ? C7 C8 H8 119.8 . . ? C7 C8 C9 120.4(4) . . ? C9 C8 H8 119.8 . . ? C8 C9 H9 119.5 . . ? C10 C9 C8 121.0(4) . . ? C10 C9 H9 119.5 . . ? C5 C10 C17 124.9(3) . . ? C9 C10 C5 119.9(4) . . ? C9 C10 C17 115.1(4) . . ? N1 C11 C12 114.6(4) . . ? O1 C11 C12 120.8(4) . . ? O1 C11 N1 124.5(4) . . ? C13 C12 C11 119.7(4) . . ? N2 C12 C11 117.2(4) . . ? N2 C12 C13 123.1(4) . . ? C12 C13 H13 120.9 . . ? C12 C13 C14 118.2(5) . . ? C14 C13 H13 120.9 . . ? C13 C14 H14 120.4 . . ? C15 C14 C13 119.3(5) . . ? C15 C14 H14 120.4 . . ? C14 C15 H15 121.0 . . ? C14 C15 C16 118.0(5) . . ? C16 C15 H15 121.0 . . ? C15 C16 H16 117.6 . . ? N2 C16 C15 124.8(5) . . ? N2 C16 H16 117.6 . . ? O2 C17 C10 125.0(4) . . ? O2 C17 O3 124.9(4) . . ? O3 C17 C10 109.9(3) . . ? C19 C18 H18 109.5 . . ? C20 C18 H18 109.5 . . ? C20 C18 C19 114.6(5) . . ? O3 C18 H18 109.5 . . ? O3 C18 C19 108.8(4) . . ? O3 C18 C20 104.7(4) . . ? C18 C19 H19A 109.5 . . ? C18 C19 H19B 109.5 . . ? C18 C19 H19C 109.5 . . ? H19A C19 H19B 109.5 . . ? H19A C19 H19C 109.5 . . ? H19B C19 H19C 109.5 . . ? C18 C20 H20A 109.5 . . ? C18 C20 H20B 109.5 . . ? C18 C20 H20C 109.5 . . ? H20A C20 H20B 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C4 N1 H1 118(3) . . ? C11 N1 C4 122.1(3) . . ? C11 N1 H1 119(3) . . ? C16 N2 C12 116.6(4) . . ? C17 O3 C18 118.1(3) . . ? 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 C1 1.904(4) . ? C1 C2 1.359(5) . ? C1 C6 1.411(5) . ? C2 H2 0.9300 . ? C2 C3 1.386(5) . ? C3 H3 0.9300 . ? C3 C4 1.362(5) . ? C4 C5 1.433(5) . ? C4 N1 1.423(5) . ? C5 C6 1.430(5) . ? C5 C10 1.432(5) . ? C6 C7 1.419(5) . ? C7 H7 0.9300 . ? C7 C8 1.352(6) . ? C8 H8 0.9300 . ? C8 C9 1.400(6) . ? C9 H9 0.9300 . ? C9 C10 1.378(5) . ? C10 C17 1.494(5) . ? C11 C12 1.504(5) . ? C11 N1 1.351(5) . ? C11 O1 1.220(5) . ? C12 C13 1.371(6) . ? C12 N2 1.344(5) . ? C13 H13 0.9300 . ? C13 C14 1.391(7) . ? C14 H14 0.9300 . ? C14 C15 1.360(7) . ? C15 H15 0.9300 . ? C15 C16 1.369(6) . ? C16 H16 0.9300 . ? C16 N2 1.321(5) . ? C17 O2 1.198(5) . ? C17 O3 1.330(5) . ? C18 H18 0.9800 . ? C18 C19 1.496(6) . ? C18 C20 1.493(7) . ? C18 O3 1.464(5) . ? C19 H19A 0.9600 . ? C19 H19B 0.9600 . ? C19 H19C 0.9600 . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 0.9600 . ? N1 H1 0.79(4) . ? 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 N1 H1 O2 0.79(4) 2.61(4) 3.104(5) 122(4) . 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 Br1 C1 C2 C3 176.2(3) . . . . ? Br1 C1 C6 C5 -173.9(3) . . . . ? Br1 C1 C6 C7 6.1(5) . . . . ? C1 C2 C3 C4 -2.0(6) . . . . ? C1 C6 C7 C8 -179.4(4) . . . . ? C2 C1 C6 C5 4.4(6) . . . . ? C2 C1 C6 C7 -175.6(4) . . . . ? C2 C3 C4 C5 3.6(6) . . . . ? C2 C3 C4 N1 -176.3(4) . . . . ? C3 C4 C5 C6 -1.2(5) . . . . ? C3 C4 C5 C10 179.1(4) . . . . ? C3 C4 N1 C11 65.5(5) . . . . ? C4 C5 C6 C1 -2.6(5) . . . . ? C4 C5 C6 C7 177.3(3) . . . . ? C4 C5 C10 C9 -177.5(4) . . . . ? C4 C5 C10 C17 5.8(6) . . . . ? C5 C4 N1 C11 -114.4(4) . . . . ? C5 C6 C7 C8 0.6(6) . . . . ? C5 C10 C17 O2 -95.4(5) . . . . ? C5 C10 C17 O3 89.4(4) . . . . ? C6 C1 C2 C3 -2.1(6) . . . . ? C6 C5 C10 C9 2.9(5) . . . . ? C6 C5 C10 C17 -173.9(3) . . . . ? C6 C7 C8 C9 1.9(7) . . . . ? C7 C8 C9 C10 -2.0(7) . . . . ? C8 C9 C10 C5 -0.4(6) . . . . ? C8 C9 C10 C17 176.7(4) . . . . ? C9 C10 C17 O2 87.7(5) . . . . ? C9 C10 C17 O3 -87.6(4) . . . . ? C10 C5 C6 C1 177.0(3) . . . . ? C10 C5 C6 C7 -3.0(5) . . . . ? C10 C17 O3 C18 170.7(3) . . . . ? C11 C12 C13 C14 177.1(4) . . . . ? C11 C12 N2 C16 -178.3(4) . . . . ? C12 C11 N1 C4 178.9(3) . . . . ? C12 C13 C14 C15 0.7(7) . . . . ? C13 C12 N2 C16 -0.1(6) . . . . ? C13 C14 C15 C16 0.7(8) . . . . ? C14 C15 C16 N2 -2.0(8) . . . . ? C15 C16 N2 C12 1.7(7) . . . . ? C19 C18 O3 C17 -77.2(5) . . . . ? C20 C18 O3 C17 159.9(4) . . . . ? N1 C4 C5 C6 178.7(3) . . . . ? N1 C4 C5 C10 -0.9(5) . . . . ? N1 C11 C12 C13 -176.3(4) . . . . ? N1 C11 C12 N2 1.9(5) . . . . ? N2 C12 C13 C14 -1.0(7) . . . . ? O1 C11 C12 C13 2.8(6) . . . . ? O1 C11 C12 N2 -179.0(4) . . . . ? O1 C11 N1 C4 -0.2(7) . . . . ? O2 C17 O3 C18 -4.6(6) . . . . ?