# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_dwb1161 _database_code_depnum_ccdc_archive 'CCDC 905968' #TrackingRef 'dwb1161.cif' _audit_creation_date 2013-01-11 _audit_creation_method ; Olex2 1.2 (compiled Dec 5 2012 16:17:34, GUI svn.r4385) ; _chemical_name_common ? _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C17 H19 Br2 N' _chemical_formula_sum 'C17 H19 Br2 N' _chemical_formula_weight 397.15 _chemical_absolute_configuration ad _chemical_melting_point ? _chemical_oxdiff_formula 'C17 H19 Br2 N1' _chemical_oxdiff_usercomment "Linda's LJM186" 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' Br Br -0.2901 2.4595 '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' _space_group_crystal_system monoclinic _space_group_IT_number 9 _space_group_name_H-M_alt 'C 1 c 1' _space_group_name_Hall 'C -2yc' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 'x, -y, z+1/2' 3 'x+1/2, y+1/2, z' 4 'x+1/2, -y+1/2, z+1/2' _cell_length_a 5.40904(18) _cell_length_b 12.6594(4) _cell_length_c 23.2463(8) _cell_angle_alpha 90.00 _cell_angle_beta 91.103(3) _cell_angle_gamma 90.00 _cell_volume 1591.51(9) _cell_formula_units_Z 4 _cell_measurement_reflns_used 4587 _cell_measurement_temperature 110.00(10) _cell_measurement_theta_max 32.1320 _cell_measurement_theta_min 3.2119 _exptl_absorpt_coefficient_mu 5.084 _exptl_absorpt_correction_T_max 0.888 _exptl_absorpt_correction_T_min 0.861 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) (compiled Aug 3 2011,13:03:54) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) ; _exptl_crystal_colour colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.658 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 792 _exptl_crystal_size_max 0.145 _exptl_crystal_size_mid 0.1289 _exptl_crystal_size_min 0.1149 _exptl_special_details ; ? ; _diffrn_reflns_av_R_equivalents 0.0202 _diffrn_reflns_av_unetI/netI 0.0340 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_l_max 32 _diffrn_reflns_limit_l_min -28 _diffrn_reflns_number 7949 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 32.20 _diffrn_reflns_theta_min 3.22 _diffrn_ambient_temperature 110.00(10) _diffrn_detector_area_resol_mean 16.1450 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.909 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega -89.00 -61.00 1.0000 15.6800 omega____ theta____ kappa____ phi______ frames - -25.0110 -178.0000 -60.0000 28 #__ type_ start__ end____ width___ exp.time_ 2 omega -98.00 26.00 1.0000 15.6800 omega____ theta____ kappa____ phi______ frames - -25.0110 0.0000 150.0000 124 #__ type_ start__ end____ width___ exp.time_ 3 omega 54.00 89.00 1.0000 15.6800 omega____ theta____ kappa____ phi______ frames - 26.5735 57.0000 0.0000 35 #__ type_ start__ end____ width___ exp.time_ 4 omega 39.00 83.00 1.0000 15.6800 omega____ theta____ kappa____ phi______ frames - 26.5735 178.0000 -120.0000 44 #__ type_ start__ end____ width___ exp.time_ 5 omega 8.00 93.00 1.0000 15.6800 omega____ theta____ kappa____ phi______ frames - 26.5735 57.0000 -30.0000 85 #__ type_ start__ end____ width___ exp.time_ 6 omega -43.00 50.00 1.0000 15.6800 omega____ theta____ kappa____ phi______ frames - 26.5735 -37.0000 -90.0000 93 ; _diffrn_measurement_device_type 'SuperNova, Single source at offset), Eos' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 -0.0724896000 _diffrn_orient_matrix_UB_12 0.0184429000 _diffrn_orient_matrix_UB_13 0.0230594000 _diffrn_orient_matrix_UB_21 0.0861292000 _diffrn_orient_matrix_UB_22 -0.0220262000 _diffrn_orient_matrix_UB_23 0.0200020000 _diffrn_orient_matrix_UB_31 0.0673333000 _diffrn_orient_matrix_UB_32 0.0480776000 _diffrn_orient_matrix_UB_33 0.0003696000 _diffrn_radiation_monochromator mirror _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.7107 _diffrn_source 'SuperNova (Mo) X-ray Source' _diffrn_standards_decay_% ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_number ? _reflns_number_gt 4268 _reflns_number_total 4415 _reflns_odcompleteness_completeness 99.73 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 24.97 _reflns_threshold_expression >2sigma(I) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) (compiled Aug 3 2011,13:03:54) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) (compiled Aug 3 2011,13:03:54) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.35.15 (release 03-08-2011 CrysAlis171 .NET) (compiled Aug 3 2011,13:03:54) ; _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement ; SHELXL, G.M. Sheldrick, Acta Cryst. (2008). A64, 112-122 ; _computing_structure_solution 'SUPERFLIP, J. Appl. Cryst. (2007) 40, 786-790' _refine_diff_density_max 0.652 _refine_diff_density_min -0.504 _refine_diff_density_rms 0.087 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.045(13) _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.048 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 216 _refine_ls_number_reflns 4415 _refine_ls_number_restraints 27 _refine_ls_R_factor_all 0.0335 _refine_ls_R_factor_gt 0.0317 _refine_ls_restrained_S_all 1.045 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0326P)^2^+2.8003P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0719 _refine_ls_wR_factor_ref 0.0730 _refine_special_details ; The structure was modelled as disordered over 4 positions. The ratio of the four disordered components were refined to 41.3 : 30.0 : 15.0 : 13.7 (total occupancy sums to 1). The ADP of each pair of carbons of the disordered dibromoethane were constrained to be the same (i.e.) C6 & C7, C6A & C7A etc). The adp of the minor components C6B, C6C, C7B and C7C were restrained to be approximately isotropic. The The pyridine and arene rings also show evidence of disorder especially of the ipso carbon bonded to the central dibromoethane. However, a suitable discrete model with each carbon placed indepentently could not be obtained as the difference in position is below the resolution of the experiment. ; _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: H6 of C6, {H14A,H14B} of C14, H7 of C7, H6A of C6A, H7B of C7B, H7A of C7A, {H15A,H15B} of C15, H9 of C9, {H16A,H16B} of C16, H6B of C6B, H6C of C6C, H7C of C7C, H5 of C5, H1 of C1, H4 of C4, H2 of C2, H10 of C10, H12 of C12, H13 of C13 At 1.5 times of: {H17A,H17B,H17C} of C17 2. Uiso/Uaniso restraints and constraints Uanis(C6C) ~ Ueq, Uanis(C7C) ~ Ueq, Uanis(C6B) ~ Ueq, Uanis(C7B) ~ Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.1 Uanis(C6) = Uanis(C7) Uanis(C6A) = Uanis(C7A) Uanis(C6B) = Uanis(C7B) Uanis(C6C) = Uanis(C7C) 3. Others 1*[Sof(C7A)+Sof(H7A)+Sof(C6A)+Sof(H6A)]+1*[Sof(C6)+Sof(H6)+Sof(C7)+Sof(H7)]+1* [Sof(C6C)+Sof(H6C)+Sof(C7C)+Sof(H7C)]+1*[Sof(C7B)+Sof(H7B)+Sof(C6B)+Sof(H6B)]= 1 with esd of 0.0001 Sof(C7A)=Sof(H7A)=Sof(C6A)=Sof(H6A) Sof(C6)=Sof(H6)=Sof(C7)=Sof(H7) Sof(C6C)=Sof(H6C)=Sof(C7C)=Sof(H7C) Sof(C7B)=Sof(H7B)=Sof(C6B)=Sof(H6B) 4.a Ternary CH refined with riding coordinates: C6(H6), C7(H7), C7A(H7A), C6A(H6A), C7B(H7B), C6C(H6C), C7C(H7C), C6B(H6B) 4.b Secondary CH2 refined with riding coordinates: C15(H15A,H15B), C16(H16A,H16B), C14(H14A,H14B) 4.c Aromatic/amide H refined with riding coordinates: C1(H1), C4(H4), C2(H2), C5(H5), C10(H10), C12(H12), C13(H13), C9(H9) 4.d Idealised Me refined as rotating group: C17(H17A,H17B,H17C) ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary iterative _atom_sites_solution_secondary difmap 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 Br1 Br -0.48810(4) -0.64410(2) -0.339370(16) 0.02120(8) Uani 1 1 d . . . Br2 Br -1.01710(4) -0.87573(3) -0.435610(16) 0.02176(8) Uani 1 1 d . . . C1 C -0.8879(8) -0.9124(3) -0.2360(2) 0.0297(9) Uani 1 1 d . . . H1 H -1.0132 -0.9057 -0.2081 0.036 Uiso 1 1 calc R . . N1 N -0.7143(7) -0.9859(3) -0.22765(15) 0.0298(7) Uani 1 1 d . . . C4 C -0.5373(9) -0.9334(4) -0.31654(19) 0.0370(10) Uani 1 1 d . A . H4 H -0.4129 -0.9445 -0.3442 0.044 Uiso 1 1 calc R . . C2 C -0.8951(10) -0.8455(4) -0.2830(3) 0.0445(12) Uani 1 1 d . A . H2 H -1.0208 -0.7935 -0.2872 0.053 Uiso 1 1 calc R . . C5 C -0.5431(8) -0.9942(3) -0.26874(18) 0.0274(8) Uani 1 1 d . . . H5 H -0.4181 -1.0463 -0.2638 0.033 Uiso 1 1 calc R . . C3 C -0.7092(13) -0.8567(4) -0.3250(3) 0.0523(15) Uani 1 1 d . . . C10 C -0.9720(9) -0.5217(3) -0.5079(2) 0.0354(9) Uani 1 1 d . . . H10 H -1.0993 -0.4707 -0.5131 0.042 Uiso 1 1 calc R . . C8 C -0.7903(14) -0.6596(5) -0.4521(3) 0.0620(18) Uani 1 1 d . . . C11 C -0.7902(7) -0.5299(3) -0.54923(17) 0.0258(7) Uani 1 1 d . A . C12 C -0.6053(8) -0.6058(3) -0.5409(2) 0.0319(9) Uani 1 1 d . . . H12 H -0.4801 -0.6139 -0.5687 0.038 Uiso 1 1 calc R A . C13 C -0.6035(10) -0.6695(4) -0.4923(3) 0.0496(14) Uani 1 1 d . A . H13 H -0.4750 -0.7197 -0.4864 0.060 Uiso 1 1 calc R . . C15 C -0.5842(8) -0.3905(3) -0.60995(18) 0.0319(8) Uani 1 1 d . A . H15A H -0.4391 -0.4367 -0.6156 0.038 Uiso 1 1 calc R . . H15B H -0.5519 -0.3480 -0.5748 0.038 Uiso 1 1 calc R . . C9 C -0.9734(11) -0.5844(4) -0.4603(2) 0.0475(12) Uani 1 1 d . A . H9 H -1.0997 -0.5765 -0.4328 0.057 Uiso 1 1 calc R . . C16 C -0.6102(8) -0.3168(4) -0.6608(2) 0.0414(10) Uani 1 1 d . . . H16A H -0.6555 -0.3588 -0.6954 0.050 Uiso 1 1 calc R . . H16B H -0.7474 -0.2670 -0.6537 0.050 Uiso 1 1 calc R . . C6 C -0.6364(17) -0.7747(6) -0.3722(4) 0.0187(17) Uani 0.413(11) 1 d P A 1 H6 H -0.5183 -0.8080 -0.3993 0.022 Uiso 0.413(11) 1 calc PR A 1 C14 C -0.8061(9) -0.4581(4) -0.6007(2) 0.0411(10) Uani 1 1 d . . . H14A H -0.8347 -0.5018 -0.6355 0.049 Uiso 1 1 calc R A . H14B H -0.9518 -0.4115 -0.5966 0.049 Uiso 1 1 calc R . . C17 C -0.3825(8) -0.2550(3) -0.6729(2) 0.0357(9) Uani 1 1 d . . . H17A H -0.4167 -0.2052 -0.7044 0.054 Uiso 1 1 calc R . . H17B H -0.2500 -0.3032 -0.6840 0.054 Uiso 1 1 calc R . . H17C H -0.3311 -0.2158 -0.6384 0.054 Uiso 1 1 calc R . . C7 C -0.8654(16) -0.7385(6) -0.4051(4) 0.0187(17) Uani 0.413(11) 1 d P A 1 H7 H -0.9822 -0.7037 -0.3782 0.022 Uiso 0.413(11) 1 calc PR A 1 C7A C -0.7770(19) -0.7004(7) -0.3863(5) 0.0120(12) Uani 0.300(4) 1 d P A 2 H7A H -0.9356 -0.6843 -0.3667 0.014 Uiso 0.300(4) 1 calc PR A 2 C6A C -0.7344(19) -0.8186(7) -0.3876(5) 0.0120(12) Uani 0.300(4) 1 d P A 2 H6A H -0.5762 -0.8331 -0.4076 0.014 Uiso 0.300(4) 1 calc PR A 2 C7B C -0.740(4) -0.7769(15) -0.4205(10) 0.015(5) Uani 0.150(12) 1 d PU A 4 H7B H -0.5750 -0.8077 -0.4295 0.018 Uiso 0.150(12) 1 calc PR A 4 C6C C -0.855(4) -0.7887(14) -0.3739(9) 0.007(4) Uani 0.137(11) 1 d PU A 3 H6C H -0.9704 -0.7358 -0.3571 0.008 Uiso 0.137(11) 1 calc PR A 3 C7C C -0.638(4) -0.7369(14) -0.4030(9) 0.007(4) Uani 0.137(11) 1 d PU A 3 H7C H -0.5188 -0.7878 -0.4201 0.008 Uiso 0.137(11) 1 calc PR A 3 C6B C -0.761(4) -0.7479(16) -0.3617(10) 0.015(5) Uani 0.150(12) 1 d PU A 4 H6B H -0.9283 -0.7182 -0.3537 0.018 Uiso 0.150(12) 1 calc PR A 4 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 0.02409(17) 0.01895(12) 0.02035(17) 0.00006(13) -0.00537(12) -0.00642(13) Br2 0.02334(17) 0.02239(13) 0.01939(17) -0.00175(13) -0.00348(12) -0.00682(13) C1 0.033(2) 0.0304(19) 0.026(2) -0.0025(14) 0.0048(17) -0.0049(15) N1 0.039(2) 0.0276(15) 0.0231(17) 0.0073(11) -0.0058(14) -0.0063(13) C4 0.044(3) 0.044(2) 0.023(2) 0.0021(16) 0.0082(18) -0.0078(19) C2 0.046(3) 0.035(2) 0.052(3) 0.013(2) -0.008(2) 0.019(2) C5 0.0255(18) 0.0289(17) 0.028(2) -0.0020(13) -0.0036(15) -0.0010(14) C3 0.067(4) 0.058(3) 0.032(3) 0.025(2) 0.001(3) 0.009(3) C10 0.038(2) 0.034(2) 0.033(2) 0.0002(15) -0.0075(18) -0.0117(17) C8 0.083(5) 0.058(3) 0.046(4) 0.038(3) 0.004(3) -0.009(3) C11 0.0307(19) 0.0267(16) 0.0198(19) 0.0049(12) -0.0069(14) -0.0065(14) C12 0.030(2) 0.0318(19) 0.034(2) -0.0003(15) -0.0100(17) -0.0027(15) C13 0.057(3) 0.032(2) 0.059(4) 0.017(2) -0.023(3) -0.001(2) C15 0.037(2) 0.0352(19) 0.023(2) 0.0063(14) -0.0078(15) -0.0066(16) C9 0.051(3) 0.055(3) 0.037(3) 0.010(2) 0.002(2) -0.019(2) C16 0.036(2) 0.054(3) 0.033(2) 0.020(2) -0.0031(18) -0.004(2) C6 0.014(3) 0.019(3) 0.023(3) 0.000(2) 0.0014(19) 0.001(2) C14 0.043(2) 0.052(3) 0.028(2) 0.0164(18) -0.0072(18) -0.002(2) C17 0.040(2) 0.035(2) 0.033(2) 0.0052(15) -0.0028(17) -0.0047(17) C7 0.014(3) 0.019(3) 0.023(3) 0.000(2) 0.0014(19) 0.001(2) C7A 0.011(3) 0.010(3) 0.015(3) 0.001(2) -0.005(2) -0.001(3) C6A 0.011(3) 0.010(3) 0.015(3) 0.001(2) -0.005(2) -0.001(3) C7B 0.014(5) 0.013(5) 0.018(6) 0.001(3) -0.001(3) -0.001(3) C6C 0.008(5) 0.005(5) 0.007(5) -0.003(3) -0.003(3) 0.001(3) C7C 0.008(5) 0.005(5) 0.007(5) -0.003(3) -0.003(3) 0.001(3) C6B 0.014(5) 0.013(5) 0.018(6) 0.001(3) -0.001(3) -0.001(3) _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 Br1 C6 1.984(8) . ? Br1 C7A 2.019(11) . ? Br1 C7C 2.043(19) . ? Br1 C6B 2.04(2) . ? Br2 C7 2.043(9) . ? Br2 C6A 2.011(10) . ? Br2 C7B 1.98(2) . ? Br2 C6C 1.998(19) . ? C1 N1 1.333(6) . ? C1 C2 1.384(6) . ? N1 C5 1.347(5) . ? C4 C5 1.353(6) . ? C4 C3 1.357(7) . ? C2 C3 1.421(8) . ? C3 C6 1.566(10) . ? C3 C6A 1.537(12) . ? C3 C6C 1.62(2) . ? C3 C6B 1.64(2) . ? C10 C11 1.392(6) . ? C10 C9 1.362(6) . ? C8 C13 1.394(10) . ? C8 C9 1.385(9) . ? C8 C7 1.541(10) . ? C8 C7A 1.615(12) . ? C8 C7B 1.68(2) . ? C8 C7C 1.70(2) . ? C11 C12 1.397(6) . ? C11 C14 1.504(5) . ? C12 C13 1.388(7) . ? C15 C16 1.511(6) . ? C15 C14 1.493(6) . ? C16 C17 1.491(6) . ? C6 C7 1.514(11) . ? C7A C6A 1.513(12) . ? C7B C6B 1.42(3) . ? C6C C7C 1.51(3) . ? 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 C6 Br1 C7A 36.4(4) . . ? C6 Br1 C7C 24.6(6) . . ? C6 Br1 C6B 22.8(6) . . ? C7A Br1 C7C 27.6(6) . . ? C7A Br1 C6B 23.7(6) . . ? C6B Br1 C7C 33.8(9) . . ? C6A Br2 C7 37.3(3) . . ? C7B Br2 C7 26.2(6) . . ? C7B Br2 C6A 26.9(7) . . ? C7B Br2 C6C 37.2(9) . . ? C6C Br2 C7 27.6(6) . . ? C6C Br2 C6A 23.7(6) . . ? N1 C1 C2 123.4(4) . . ? C1 N1 C5 116.3(4) . . ? C5 C4 C3 119.9(4) . . ? C1 C2 C3 118.2(4) . . ? N1 C5 C4 124.4(4) . . ? C4 C3 C2 117.7(4) . . ? C4 C3 C6 113.2(6) . . ? C4 C3 C6A 114.2(6) . . ? C4 C3 C6C 143.6(9) . . ? C4 C3 C6B 141.8(10) . . ? C2 C3 C6 127.3(5) . . ? C2 C3 C6A 124.6(6) . . ? C2 C3 C6C 95.1(9) . . ? C2 C3 C6B 99.1(9) . . ? C6 C3 C6C 44.0(8) . . ? C6 C3 C6B 28.7(8) . . ? C6A C3 C6 31.5(5) . . ? C6A C3 C6C 30.0(8) . . ? C6A C3 C6B 39.9(10) . . ? C6C C3 C6B 27.5(9) . . ? C9 C10 C11 122.1(5) . . ? C13 C8 C7 128.4(6) . . ? C13 C8 C7A 125.9(7) . . ? C13 C8 C7B 95.8(8) . . ? C13 C8 C7C 92.9(8) . . ? C9 C8 C13 119.7(4) . . ? C9 C8 C7 110.2(6) . . ? C9 C8 C7A 111.7(6) . . ? C9 C8 C7B 141.2(9) . . ? C9 C8 C7C 145.3(9) . . ? C7 C8 C7A 29.3(4) . . ? C7 C8 C7B 32.6(8) . . ? C7 C8 C7C 44.2(8) . . ? C7A C8 C7B 45.3(8) . . ? C7A C8 C7C 33.8(8) . . ? C7B C8 C7C 29.0(9) . . ? C10 C11 C12 118.0(4) . . ? C10 C11 C14 118.2(4) . . ? C12 C11 C14 123.8(4) . . ? C13 C12 C11 120.4(5) . . ? C12 C13 C8 119.9(5) . . ? C14 C15 C16 113.8(3) . . ? C10 C9 C8 119.8(5) . . ? C17 C16 C15 114.0(4) . . ? C3 C6 Br1 112.8(6) . . ? C7 C6 Br1 105.2(5) . . ? C7 C6 C3 109.9(6) . . ? C15 C14 C11 115.3(4) . . ? C8 C7 Br2 114.5(6) . . ? C6 C7 Br2 103.7(5) . . ? C6 C7 C8 109.3(6) . . ? C8 C7A Br1 114.8(6) . . ? C6A C7A Br1 104.0(6) . . ? C6A C7A C8 107.6(7) . . ? C3 C6A Br2 117.8(6) . . ? C7A C6A Br2 104.6(6) . . ? C7A C6A C3 107.6(7) . . ? C8 C7B Br2 111.5(12) . . ? C6B C7B Br2 105.0(14) . . ? C6B C7B C8 100.3(14) . . ? C3 C6C Br2 114.3(10) . . ? C7C C6C Br2 104.6(12) . . ? C7C C6C C3 100.0(13) . . ? C8 C7C Br1 109.6(9) . . ? C6C C7C Br1 103.1(12) . . ? C6C C7C C8 100.3(12) . . ? C3 C6B Br1 107.0(12) . . ? C7B C6B Br1 109.9(14) . . ? C7B C6B C3 105.5(16) . . ? loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist _exptl_oxdiff_crystal_face_indexfrac_h _exptl_oxdiff_crystal_face_indexfrac_k _exptl_oxdiff_crystal_face_indexfrac_l _exptl_oxdiff_crystal_face_x _exptl_oxdiff_crystal_face_y _exptl_oxdiff_crystal_face_z 0 18 0 0.0711 -0.0006 18.0018 0.0029 0.3321 -0.3965 0.8654 0 -18 0 0.0577 0.0006 -18.0018 -0.0029 -0.3321 0.3965 -0.8654 -8 2 0 0.0596 -8.0005 2.0012 0.0048 0.6170 -0.7331 -0.4425 8 -1 0 0.0565 8.0005 -1.0011 -0.0047 -0.5985 0.7110 0.4906 1 0 33 0.0673 1.0004 -0.0008 32.9928 0.6883 0.7461 0.0795 -1 0 -33 0.0476 -1.0004 0.0008 -32.9928 -0.6883 -0.7461 -0.0795 data_dwb0823m _database_code_depnum_ccdc_archive 'CCDC 905969' #TrackingRef 'Cif_submit.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C21 H27 N O, I2' _chemical_formula_sum 'C21 H27 I2 N O' _chemical_formula_weight 563.24 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' I I -0.4742 1.8119 '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 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 9.5988(17) _cell_length_b 10.6104(19) _cell_length_c 11.461(2) _cell_angle_alpha 99.655(3) _cell_angle_beta 95.039(3) _cell_angle_gamma 109.933(3) _cell_volume 1068.4(3) _cell_formula_units_Z 2 _cell_measurement_temperature 110(2) _cell_measurement_reflns_used 2483 _cell_measurement_theta_min 2.29 _cell_measurement_theta_max 28.29 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.12 _exptl_crystal_size_mid 0.10 _exptl_crystal_size_min 0.09 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.751 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 548 _exptl_absorpt_coefficient_mu 2.952 _exptl_absorpt_correction_type Multi-scan _exptl_absorpt_correction_T_min 0.606 _exptl_absorpt_correction_T_max 0.767 _exptl_absorpt_process_details 'SADABS v2.03 (Sheldrick)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 110(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 10215 _diffrn_reflns_av_R_equivalents 0.0434 _diffrn_reflns_av_sigmaI/netI 0.0808 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_theta_min 1.82 _diffrn_reflns_theta_max 28.32 _reflns_number_total 5208 _reflns_number_gt 3456 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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^)+(0.0273P)^2^+0.0000P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 5208 _refine_ls_number_parameters 227 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0772 _refine_ls_R_factor_gt 0.0400 _refine_ls_wR_factor_ref 0.0805 _refine_ls_wR_factor_gt 0.0728 _refine_ls_goodness_of_fit_ref 1.008 _refine_ls_restrained_S_all 1.008 _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 C1 C 1.0120(6) 0.3701(5) 1.3653(5) 0.0219(12) Uani 1 1 d . . . H1 H 0.9468 0.3571 1.4236 0.026 Uiso 1 1 calc R . . C2 C 0.9492(6) 0.3466(5) 1.2465(4) 0.0197(12) Uani 1 1 d . . . H2 H 0.8434 0.3170 1.2252 0.024 Uiso 1 1 calc R . . C3 C 1.0418(6) 0.3664(5) 1.1571(4) 0.0157(11) Uani 1 1 d . . . C4 C 1.1969(6) 0.4114(5) 1.1982(5) 0.0210(11) Uani 1 1 d . . . H4 H 1.2654 0.4281 1.1426 0.025 Uiso 1 1 calc R . . C5 C 1.2504(6) 0.4316(5) 1.3178(5) 0.0228(12) Uani 1 1 d . . . H5 H 1.3558 0.4620 1.3418 0.027 Uiso 1 1 calc R . . C6 C 0.9875(6) 0.3418(5) 1.0331(5) 0.0202(12) Uani 1 1 d . . . H6 H 1.0612 0.3577 0.9816 0.024 Uiso 1 1 calc R . . C7 C 0.8426(6) 0.2982(5) 0.9795(5) 0.0188(11) Uani 1 1 d . . . H7 H 0.7679 0.2841 1.0301 0.023 Uiso 1 1 calc R . . C8 C 0.7914(6) 0.2710(5) 0.8501(5) 0.0176(11) Uani 1 1 d . . . C9 C 0.8910(6) 0.2736(5) 0.7668(5) 0.0205(12) Uani 1 1 d . . . H9 H 0.9944 0.2946 0.7939 0.025 Uiso 1 1 calc R . . C10 C 0.8388(6) 0.2457(5) 0.6463(4) 0.0200(11) Uani 1 1 d . . . H10 H 0.9062 0.2455 0.5904 0.024 Uiso 1 1 calc R . . C11 C 0.6888(6) 0.2177(5) 0.6052(5) 0.0210(12) Uani 1 1 d . . . C12 C 0.5888(6) 0.2168(6) 0.6853(5) 0.0238(13) Uani 1 1 d . . . H12 H 0.4864 0.1996 0.6577 0.029 Uiso 1 1 calc R . . C13 C 0.6409(6) 0.2413(5) 0.8061(5) 0.0222(12) Uani 1 1 d . . . H13 H 0.5720 0.2378 0.8612 0.027 Uiso 1 1 calc R . . C14 C 0.5041(6) 0.1689(6) 0.4293(5) 0.0236(13) Uani 1 1 d . . . H14A H 0.4746 0.2480 0.4583 0.028 Uiso 1 1 calc R . . H14B H 0.4329 0.0860 0.4495 0.028 Uiso 1 1 calc R . . C15 C 0.5049(6) 0.1483(6) 0.2951(5) 0.0221(12) Uani 1 1 d . . . H15A H 0.5429 0.0737 0.2701 0.027 Uiso 1 1 calc R . . H15B H 0.5759 0.2332 0.2778 0.027 Uiso 1 1 calc R . . C16 C 0.3526(6) 0.1132(6) 0.2195(4) 0.0203(12) Uani 1 1 d . . . H16A H 0.2809 0.0276 0.2351 0.024 Uiso 1 1 calc R . . H16B H 0.3138 0.1875 0.2432 0.024 Uiso 1 1 calc R . . C17 C 0.3629(6) 0.0947(6) 0.0863(5) 0.0219(12) Uani 1 1 d . . . H17A H 0.4374 0.1795 0.0719 0.026 Uiso 1 1 calc R . . H17B H 0.4000 0.0191 0.0631 0.026 Uiso 1 1 calc R . . C18 C 0.2154(6) 0.0632(6) 0.0069(4) 0.0203(12) Uani 1 1 d . . . H18A H 0.1778 0.1384 0.0300 0.024 Uiso 1 1 calc R . . H18B H 0.1409 -0.0222 0.0203 0.024 Uiso 1 1 calc R . . C19 C 0.2294(6) 0.0461(6) -0.1265(5) 0.0214(12) Uani 1 1 d . . . H19A H 0.3025 0.1323 -0.1398 0.026 Uiso 1 1 calc R . . H19B H 0.2697 -0.0274 -0.1487 0.026 Uiso 1 1 calc R . . C20 C 0.0816(6) 0.0111(6) -0.2088(5) 0.0242(12) Uani 1 1 d . . . H20A H 0.0370 0.0806 -0.1826 0.029 Uiso 1 1 calc R . . H20B H 0.0111 -0.0790 -0.2007 0.029 Uiso 1 1 calc R . . C21 C 0.0995(7) 0.0057(6) -0.3409(5) 0.0327(15) Uani 1 1 d . . . H21A H 0.1630 0.0965 -0.3507 0.049 Uiso 1 1 calc R . . H21B H 0.0007 -0.0220 -0.3897 0.049 Uiso 1 1 calc R . . H21C H 0.1464 -0.0609 -0.3669 0.049 Uiso 1 1 calc R . . N1 N 1.1612(5) 0.4105(5) 1.4028(4) 0.0219(11) Uani 1 1 d . . . O1 O 0.6540(4) 0.1938(4) 0.4818(3) 0.0253(9) Uani 1 1 d . . . I1 I 1.26194(4) 0.43377(4) 1.60335(3) 0.02042(10) Uani 1 1 d . . . I2 I 1.37247(4) 0.46711(4) 1.84811(3) 0.02631(11) 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 C1 0.030(3) 0.026(3) 0.013(3) 0.009(2) 0.010(2) 0.012(3) C2 0.012(3) 0.025(3) 0.015(3) 0.000(2) -0.006(2) 0.001(2) C3 0.018(3) 0.009(2) 0.022(3) 0.006(2) 0.003(2) 0.005(2) C4 0.017(3) 0.021(3) 0.023(3) 0.003(2) 0.002(2) 0.005(2) C5 0.022(3) 0.022(3) 0.024(3) 0.006(2) 0.002(2) 0.007(2) C6 0.017(3) 0.015(3) 0.034(3) 0.011(2) 0.014(2) 0.007(2) C7 0.022(3) 0.018(3) 0.017(3) 0.002(2) 0.001(2) 0.010(2) C8 0.015(3) 0.014(3) 0.024(3) 0.004(2) 0.001(2) 0.006(2) C9 0.018(3) 0.023(3) 0.023(3) 0.009(2) 0.004(2) 0.009(2) C10 0.017(3) 0.024(3) 0.019(3) 0.005(2) 0.006(2) 0.007(2) C11 0.025(3) 0.016(3) 0.024(3) 0.008(2) 0.004(2) 0.008(2) C12 0.018(3) 0.024(3) 0.032(3) 0.010(3) 0.010(3) 0.008(2) C13 0.017(3) 0.019(3) 0.028(3) 0.002(2) 0.006(2) 0.004(2) C14 0.012(3) 0.024(3) 0.035(3) 0.008(3) 0.001(2) 0.007(2) C15 0.021(3) 0.024(3) 0.023(3) 0.006(2) 0.008(2) 0.007(2) C16 0.016(3) 0.023(3) 0.022(3) 0.002(2) 0.002(2) 0.010(2) C17 0.016(3) 0.026(3) 0.023(3) 0.007(2) 0.005(2) 0.006(2) C18 0.020(3) 0.023(3) 0.018(3) 0.008(2) 0.003(2) 0.007(2) C19 0.018(3) 0.023(3) 0.023(3) 0.006(2) 0.006(2) 0.005(2) C20 0.026(3) 0.026(3) 0.022(3) 0.004(2) 0.006(2) 0.011(3) C21 0.040(4) 0.035(4) 0.024(3) 0.008(3) 0.003(3) 0.016(3) N1 0.026(3) 0.021(3) 0.014(2) -0.002(2) 0.002(2) 0.006(2) O1 0.018(2) 0.040(2) 0.0182(19) 0.0047(18) 0.0005(16) 0.0127(18) I1 0.0165(2) 0.0230(2) 0.0220(2) 0.00396(16) 0.00441(16) 0.00746(16) I2 0.0206(2) 0.0374(3) 0.0218(2) 0.00586(18) 0.00411(18) 0.01154(19) _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 N1 1.353(7) . ? C1 C2 1.385(7) . ? C1 H1 0.9500 . ? C2 C3 1.411(7) . ? C2 H2 0.9500 . ? C3 C4 1.408(7) . ? C3 C6 1.418(7) . ? C4 C5 1.375(7) . ? C4 H4 0.9500 . ? C5 N1 1.350(6) . ? C5 H5 0.9500 . ? C6 C7 1.357(7) . ? C6 H6 0.9500 . ? C7 C8 1.468(7) . ? C7 H7 0.9500 . ? C8 C13 1.396(7) . ? C8 C9 1.406(7) . ? C9 C10 1.374(7) . ? C9 H9 0.9500 . ? C10 C11 1.387(7) . ? C10 H10 0.9500 . ? C11 O1 1.384(6) . ? C11 C12 1.385(7) . ? C12 C13 1.379(8) . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? C14 O1 1.427(6) . ? C14 C15 1.518(7) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 C16 1.524(7) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 C17 1.523(7) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 C18 1.514(7) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 C19 1.533(6) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 C20 1.526(7) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C20 C21 1.533(7) . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? N1 I1 2.352(4) . ? I1 I2 2.8298(7) . ? 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 N1 C1 C2 123.6(5) . . ? N1 C1 H1 118.2 . . ? C2 C1 H1 118.2 . . ? C1 C2 C3 120.2(5) . . ? C1 C2 H2 119.9 . . ? C3 C2 H2 119.9 . . ? C4 C3 C2 115.4(5) . . ? C4 C3 C6 120.4(5) . . ? C2 C3 C6 124.2(5) . . ? C5 C4 C3 120.9(5) . . ? C5 C4 H4 119.5 . . ? C3 C4 H4 119.5 . . ? N1 C5 C4 123.5(5) . . ? N1 C5 H5 118.2 . . ? C4 C5 H5 118.2 . . ? C7 C6 C3 127.6(5) . . ? C7 C6 H6 116.2 . . ? C3 C6 H6 116.2 . . ? C6 C7 C8 125.7(5) . . ? C6 C7 H7 117.2 . . ? C8 C7 H7 117.2 . . ? C13 C8 C9 117.9(5) . . ? C13 C8 C7 120.6(5) . . ? C9 C8 C7 121.6(5) . . ? C10 C9 C8 120.0(5) . . ? C10 C9 H9 120.0 . . ? C8 C9 H9 120.0 . . ? C9 C10 C11 120.8(5) . . ? C9 C10 H10 119.6 . . ? C11 C10 H10 119.6 . . ? O1 C11 C12 125.6(5) . . ? O1 C11 C10 114.0(4) . . ? C12 C11 C10 120.4(5) . . ? C13 C12 C11 118.6(5) . . ? C13 C12 H12 120.7 . . ? C11 C12 H12 120.7 . . ? C12 C13 C8 122.3(5) . . ? C12 C13 H13 118.9 . . ? C8 C13 H13 118.9 . . ? O1 C14 C15 105.6(4) . . ? O1 C14 H14A 110.6 . . ? C15 C14 H14A 110.6 . . ? O1 C14 H14B 110.6 . . ? C15 C14 H14B 110.6 . . ? H14A C14 H14B 108.8 . . ? C14 C15 C16 114.8(4) . . ? C14 C15 H15A 108.6 . . ? C16 C15 H15A 108.6 . . ? C14 C15 H15B 108.6 . . ? C16 C15 H15B 108.6 . . ? H15A C15 H15B 107.5 . . ? C17 C16 C15 111.6(4) . . ? C17 C16 H16A 109.3 . . ? C15 C16 H16A 109.3 . . ? C17 C16 H16B 109.3 . . ? C15 C16 H16B 109.3 . . ? H16A C16 H16B 108.0 . . ? C18 C17 C16 113.9(4) . . ? C18 C17 H17A 108.8 . . ? C16 C17 H17A 108.8 . . ? C18 C17 H17B 108.8 . . ? C16 C17 H17B 108.8 . . ? H17A C17 H17B 107.7 . . ? C17 C18 C19 112.7(4) . . ? C17 C18 H18A 109.0 . . ? C19 C18 H18A 109.0 . . ? C17 C18 H18B 109.0 . . ? C19 C18 H18B 109.0 . . ? H18A C18 H18B 107.8 . . ? C20 C19 C18 113.8(4) . . ? C20 C19 H19A 108.8 . . ? C18 C19 H19A 108.8 . . ? C20 C19 H19B 108.8 . . ? C18 C19 H19B 108.8 . . ? H19A C19 H19B 107.7 . . ? C19 C20 C21 113.2(5) . . ? C19 C20 H20A 108.9 . . ? C21 C20 H20A 108.9 . . ? C19 C20 H20B 108.9 . . ? C21 C20 H20B 108.9 . . ? H20A C20 H20B 107.8 . . ? C20 C21 H21A 109.5 . . ? C20 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C20 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C5 N1 C1 116.4(4) . . ? C5 N1 I1 121.1(4) . . ? C1 N1 I1 122.5(3) . . ? C11 O1 C14 119.1(4) . . ? N1 I1 I2 177.19(11) . . ? 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 N1 C1 C2 C3 -0.9(8) . . . . ? C1 C2 C3 C4 -0.6(7) . . . . ? C1 C2 C3 C6 178.4(5) . . . . ? C2 C3 C4 C5 1.0(7) . . . . ? C6 C3 C4 C5 -178.1(5) . . . . ? C3 C4 C5 N1 0.0(8) . . . . ? C4 C3 C6 C7 179.9(5) . . . . ? C2 C3 C6 C7 0.9(8) . . . . ? C3 C6 C7 C8 -178.4(5) . . . . ? C6 C7 C8 C13 -172.8(5) . . . . ? C6 C7 C8 C9 7.4(8) . . . . ? C13 C8 C9 C10 -0.8(8) . . . . ? C7 C8 C9 C10 179.1(5) . . . . ? C8 C9 C10 C11 1.4(8) . . . . ? C9 C10 C11 O1 179.0(5) . . . . ? C9 C10 C11 C12 -0.3(8) . . . . ? O1 C11 C12 C13 179.4(5) . . . . ? C10 C11 C12 C13 -1.4(8) . . . . ? C11 C12 C13 C8 2.0(8) . . . . ? C9 C8 C13 C12 -0.9(8) . . . . ? C7 C8 C13 C12 179.2(5) . . . . ? O1 C14 C15 C16 177.3(4) . . . . ? C14 C15 C16 C17 179.8(5) . . . . ? C15 C16 C17 C18 -178.5(5) . . . . ? C16 C17 C18 C19 179.6(5) . . . . ? C17 C18 C19 C20 178.7(5) . . . . ? C18 C19 C20 C21 175.4(5) . . . . ? C4 C5 N1 C1 -1.4(8) . . . . ? C4 C5 N1 I1 175.9(4) . . . . ? C2 C1 N1 C5 1.8(8) . . . . ? C2 C1 N1 I1 -175.4(4) . . . . ? C12 C11 O1 C14 1.6(8) . . . . ? C10 C11 O1 C14 -177.7(5) . . . . ? C15 C14 O1 C11 179.5(4) . . . . ? _diffrn_measured_fraction_theta_max 0.979 _diffrn_reflns_theta_full 28.32 _diffrn_measured_fraction_theta_full 0.979 _refine_diff_density_max 0.998 _refine_diff_density_min -0.917 _refine_diff_density_rms 0.164 data_dwb0924m _database_code_depnum_ccdc_archive 'CCDC 905970' #TrackingRef 'Cif_submit.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C21 H27 Br N O, Br' _chemical_formula_sum 'C21 H27 Br2 N O' _chemical_formula_weight 469.26 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' Br Br -0.2901 2.4595 '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_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 4.8844(6) _cell_length_b 8.1363(9) _cell_length_c 25.803(3) _cell_angle_alpha 93.248(2) _cell_angle_beta 92.730(3) _cell_angle_gamma 90.372(3) _cell_volume 1022.6(2) _cell_formula_units_Z 2 _cell_measurement_temperature 110(2) _cell_measurement_reflns_used 1906 _cell_measurement_theta_min 2.37 _cell_measurement_theta_max 29.87 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.19 _exptl_crystal_size_min 0.04 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.524 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 476 _exptl_absorpt_coefficient_mu 3.972 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.691 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details 'SADABS v2.10; (Sheldrick)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 110(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'CCD area detector' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 15504 _diffrn_reflns_av_R_equivalents 0.0228 _diffrn_reflns_av_sigmaI/netI 0.0269 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -35 _diffrn_reflns_limit_l_max 35 _diffrn_reflns_theta_min 2.37 _diffrn_reflns_theta_max 30.02 _reflns_number_total 5824 _reflns_number_gt 5040 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker SMART' _computing_cell_refinement 'Bruker SMART' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _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. H1a, the NH hydrogen, was found by difference map after all other atoms were located. ; _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^)+(0.0273P)^2^+0.6159P] 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 5824 _refine_ls_number_parameters 231 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0329 _refine_ls_R_factor_gt 0.0264 _refine_ls_wR_factor_ref 0.0641 _refine_ls_wR_factor_gt 0.0610 _refine_ls_goodness_of_fit_ref 1.033 _refine_ls_restrained_S_all 1.033 _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 Br1 Br 1.54091(3) -0.28134(2) 0.454741(6) 0.02012(5) Uani 1 1 d . . . Br2 Br 0.54203(4) -0.26882(2) 0.714403(7) 0.02799(6) Uani 1 1 d . . . C1 C 0.9929(4) -0.3910(2) 0.57130(7) 0.0223(3) Uani 1 1 d . . . H1 H 1.0198 -0.5048 0.5629 0.027 Uiso 1 1 calc R . . C2 C 0.8125(4) -0.3419(2) 0.60862(7) 0.0201(3) Uani 1 1 d . . . H2 H 0.7164 -0.4222 0.6262 0.024 Uiso 1 1 calc R . . C3 C 0.7702(3) -0.1740(2) 0.62082(6) 0.0166(3) Uani 1 1 d . . . C4 C 0.9100(3) -0.0600(2) 0.59243(6) 0.0186(3) Uani 1 1 d . . . H4 H 0.8805 0.0547 0.5984 0.022 Uiso 1 1 calc R . . C5 C 1.0896(3) -0.1153(2) 0.55592(7) 0.0206(3) Uani 1 1 d . . . H5 H 1.1858 -0.0385 0.5370 0.025 Uiso 1 1 calc R . . C6 C 0.5858(3) -0.1168(2) 0.66181(6) 0.0171(3) Uani 1 1 d . . . C7 C 0.4656(3) 0.0309(2) 0.66248(6) 0.0180(3) Uani 1 1 d . . . H7 H 0.5151 0.0940 0.6344 0.022 Uiso 1 1 calc R . . C8 C 0.2754(3) 0.1174(2) 0.69655(6) 0.0180(3) Uani 1 1 d . . . C9 C 0.1334(3) 0.0524(2) 0.73673(7) 0.0204(3) Uani 1 1 d . . . H9 H 0.1611 -0.0592 0.7446 0.025 Uiso 1 1 calc R . . C10 C -0.0484(4) 0.1484(2) 0.76551(7) 0.0209(3) Uani 1 1 d . . . H10 H -0.1426 0.1022 0.7927 0.025 Uiso 1 1 calc R . . C11 C -0.0908(3) 0.3114(2) 0.75424(6) 0.0185(3) Uani 1 1 d . . . C12 C 0.0473(4) 0.3784(2) 0.71402(7) 0.0208(3) Uani 1 1 d . . . H12 H 0.0188 0.4900 0.7062 0.025 Uiso 1 1 calc R . . C13 C 0.2249(4) 0.2824(2) 0.68564(7) 0.0204(3) Uani 1 1 d . . . H13 H 0.3153 0.3287 0.6581 0.025 Uiso 1 1 calc R . . C14 C -0.4080(4) 0.3593(2) 0.82158(7) 0.0232(3) Uani 1 1 d . . . H14A H -0.2798 0.3290 0.8503 0.028 Uiso 1 1 calc R . . H14B H -0.5180 0.2607 0.8094 0.028 Uiso 1 1 calc R . . C15 C -0.5941(4) 0.4967(2) 0.84012(7) 0.0243(4) Uani 1 1 d . . . H15A H -0.7132 0.4543 0.8665 0.029 Uiso 1 1 calc R . . H15B H -0.7142 0.5281 0.8104 0.029 Uiso 1 1 calc R . . C16 C -0.4440(4) 0.6503(2) 0.86360(7) 0.0242(4) Uani 1 1 d . . . H16A H -0.3259 0.6944 0.8374 0.029 Uiso 1 1 calc R . . H16B H -0.3244 0.6203 0.8936 0.029 Uiso 1 1 calc R . . C17 C -0.6437(4) 0.7835(2) 0.88152(8) 0.0278(4) Uani 1 1 d . . . H17A H -0.7643 0.8112 0.8514 0.033 Uiso 1 1 calc R . . H17B H -0.7611 0.7381 0.9076 0.033 Uiso 1 1 calc R . . C18 C -0.5069(4) 0.9413(2) 0.90510(8) 0.0264(4) Uani 1 1 d . . . H18A H -0.4019 0.9926 0.8783 0.032 Uiso 1 1 calc R . . H18B H -0.3756 0.9135 0.9336 0.032 Uiso 1 1 calc R . . C19 C -0.7134(4) 1.0654(2) 0.92627(8) 0.0275(4) Uani 1 1 d . . . H19A H -0.8306 1.1024 0.8969 0.033 Uiso 1 1 calc R . . H19B H -0.8333 1.0092 0.9497 0.033 Uiso 1 1 calc R . . C20 C -0.5835(4) 1.2162(2) 0.95576(8) 0.0267(4) Uani 1 1 d . . . H20A H -0.4694 1.2757 0.9321 0.032 Uiso 1 1 calc R . . H20B H -0.4620 1.1801 0.9847 0.032 Uiso 1 1 calc R . . C21 C -0.7982(4) 1.3332(3) 0.97762(9) 0.0331(4) Uani 1 1 d . . . H21A H -0.9149 1.3723 0.9490 0.050 Uiso 1 1 calc R . . H21B H -0.7063 1.4273 0.9967 0.050 Uiso 1 1 calc R . . H21C H -0.9110 1.2750 1.0012 0.050 Uiso 1 1 calc R . . N1 N 1.1294(3) -0.27760(19) 0.54699(6) 0.0209(3) Uani 1 1 d . . . H1A H 1.248(6) -0.304(3) 0.5231(11) 0.049(8) Uiso 1 1 d . . . O1 O -0.2590(3) 0.41815(15) 0.77988(5) 0.0217(2) 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 0.02261(9) 0.01807(8) 0.02050(9) 0.00307(6) 0.00695(6) 0.00332(6) Br2 0.03658(11) 0.02057(9) 0.02946(10) 0.01039(7) 0.01723(8) 0.01020(7) C1 0.0243(8) 0.0186(8) 0.0238(8) -0.0018(6) 0.0031(7) 0.0038(6) C2 0.0220(8) 0.0171(7) 0.0213(8) 0.0002(6) 0.0037(6) 0.0022(6) C3 0.0151(7) 0.0180(7) 0.0166(7) 0.0004(6) 0.0005(6) 0.0033(6) C4 0.0190(7) 0.0181(7) 0.0188(8) 0.0008(6) 0.0024(6) 0.0019(6) C5 0.0185(8) 0.0245(8) 0.0189(8) 0.0014(6) 0.0028(6) -0.0004(6) C6 0.0186(7) 0.0169(7) 0.0162(7) 0.0020(6) 0.0038(6) 0.0004(6) C7 0.0195(7) 0.0175(7) 0.0173(7) 0.0014(6) 0.0035(6) 0.0026(6) C8 0.0184(7) 0.0175(7) 0.0183(8) -0.0003(6) 0.0031(6) 0.0024(6) C9 0.0227(8) 0.0168(7) 0.0224(8) 0.0017(6) 0.0061(6) 0.0029(6) C10 0.0225(8) 0.0212(8) 0.0195(8) 0.0009(6) 0.0066(6) 0.0022(6) C11 0.0176(7) 0.0201(8) 0.0176(8) -0.0021(6) 0.0027(6) 0.0032(6) C12 0.0250(8) 0.0182(8) 0.0199(8) 0.0026(6) 0.0054(6) 0.0048(6) C13 0.0243(8) 0.0191(8) 0.0187(8) 0.0035(6) 0.0066(6) 0.0045(6) C14 0.0238(8) 0.0230(8) 0.0234(9) -0.0007(7) 0.0091(7) 0.0020(7) C15 0.0214(8) 0.0258(9) 0.0255(9) -0.0042(7) 0.0070(7) 0.0026(7) C16 0.0221(8) 0.0272(9) 0.0229(9) -0.0039(7) 0.0046(7) 0.0033(7) C17 0.0230(9) 0.0282(9) 0.0317(10) -0.0075(8) 0.0054(7) 0.0024(7) C18 0.0240(9) 0.0266(9) 0.0285(9) -0.0032(7) 0.0061(7) 0.0033(7) C19 0.0249(9) 0.0269(9) 0.0303(10) -0.0050(7) 0.0043(7) 0.0030(7) C20 0.0258(9) 0.0262(9) 0.0280(9) -0.0022(7) 0.0066(7) -0.0001(7) C21 0.0328(10) 0.0292(10) 0.0370(11) -0.0071(8) 0.0089(8) 0.0015(8) N1 0.0188(7) 0.0259(7) 0.0180(7) -0.0022(6) 0.0033(5) 0.0034(6) O1 0.0239(6) 0.0212(6) 0.0207(6) 0.0006(5) 0.0092(5) 0.0067(5) _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 Br1 H1A 2.34(3) . ? Br2 C6 1.9058(16) . ? C1 N1 1.337(2) . ? C1 C2 1.380(2) . ? C1 H1 0.9500 . ? C2 C3 1.403(2) . ? C2 H2 0.9500 . ? C3 C4 1.407(2) . ? C3 C6 1.479(2) . ? C4 C5 1.377(2) . ? C4 H4 0.9500 . ? C5 N1 1.345(2) . ? C5 H5 0.9500 . ? C6 C7 1.341(2) . ? C7 C8 1.465(2) . ? C7 H7 0.9500 . ? C8 C9 1.400(2) . ? C8 C13 1.408(2) . ? C9 C10 1.399(2) . ? C9 H9 0.9500 . ? C10 C11 1.389(2) . ? C10 H10 0.9500 . ? C11 O1 1.3648(19) . ? C11 C12 1.398(2) . ? C12 C13 1.380(2) . ? C12 H12 0.9500 . ? C13 H13 0.9500 . ? C14 O1 1.430(2) . ? C14 C15 1.516(2) . ? C14 H14A 0.9900 . ? C14 H14B 0.9900 . ? C15 C16 1.526(3) . ? C15 H15A 0.9900 . ? C15 H15B 0.9900 . ? C16 C17 1.530(2) . ? C16 H16A 0.9900 . ? C16 H16B 0.9900 . ? C17 C18 1.525(3) . ? C17 H17A 0.9900 . ? C17 H17B 0.9900 . ? C18 C19 1.529(2) . ? C18 H18A 0.9900 . ? C18 H18B 0.9900 . ? C19 C20 1.525(3) . ? C19 H19A 0.9900 . ? C19 H19B 0.9900 . ? C20 C21 1.527(3) . ? C20 H20A 0.9900 . ? C20 H20B 0.9900 . ? C21 H21A 0.9800 . ? C21 H21B 0.9800 . ? C21 H21C 0.9800 . ? N1 H1A 0.89(3) . ? 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 N1 C1 C2 119.62(16) . . ? N1 C1 H1 120.2 . . ? C2 C1 H1 120.2 . . ? C1 C2 C3 120.41(16) . . ? C1 C2 H2 119.8 . . ? C3 C2 H2 119.8 . . ? C2 C3 C4 117.56(15) . . ? C2 C3 C6 121.91(15) . . ? C4 C3 C6 120.53(14) . . ? C5 C4 C3 119.74(16) . . ? C5 C4 H4 120.1 . . ? C3 C4 H4 120.1 . . ? N1 C5 C4 120.20(16) . . ? N1 C5 H5 119.9 . . ? C4 C5 H5 119.9 . . ? C7 C6 C3 122.77(15) . . ? C7 C6 Br2 123.06(12) . . ? C3 C6 Br2 114.15(11) . . ? C6 C7 C8 134.66(16) . . ? C6 C7 H7 112.7 . . ? C8 C7 H7 112.7 . . ? C9 C8 C13 117.47(15) . . ? C9 C8 C7 127.31(15) . . ? C13 C8 C7 115.16(15) . . ? C10 C9 C8 121.31(16) . . ? C10 C9 H9 119.3 . . ? C8 C9 H9 119.3 . . ? C11 C10 C9 119.77(16) . . ? C11 C10 H10 120.1 . . ? C9 C10 H10 120.1 . . ? O1 C11 C10 125.37(15) . . ? O1 C11 C12 114.77(15) . . ? C10 C11 C12 119.86(15) . . ? C13 C12 C11 119.92(16) . . ? C13 C12 H12 120.0 . . ? C11 C12 H12 120.0 . . ? C12 C13 C8 121.65(16) . . ? C12 C13 H13 119.2 . . ? C8 C13 H13 119.2 . . ? O1 C14 C15 107.48(15) . . ? O1 C14 H14A 110.2 . . ? C15 C14 H14A 110.2 . . ? O1 C14 H14B 110.2 . . ? C15 C14 H14B 110.2 . . ? H14A C14 H14B 108.5 . . ? C14 C15 C16 114.51(15) . . ? C14 C15 H15A 108.6 . . ? C16 C15 H15A 108.6 . . ? C14 C15 H15B 108.6 . . ? C16 C15 H15B 108.6 . . ? H15A C15 H15B 107.6 . . ? C15 C16 C17 111.74(15) . . ? C15 C16 H16A 109.3 . . ? C17 C16 H16A 109.3 . . ? C15 C16 H16B 109.3 . . ? C17 C16 H16B 109.3 . . ? H16A C16 H16B 107.9 . . ? C18 C17 C16 114.49(16) . . ? C18 C17 H17A 108.6 . . ? C16 C17 H17A 108.6 . . ? C18 C17 H17B 108.6 . . ? C16 C17 H17B 108.6 . . ? H17A C17 H17B 107.6 . . ? C17 C18 C19 112.58(16) . . ? C17 C18 H18A 109.1 . . ? C19 C18 H18A 109.1 . . ? C17 C18 H18B 109.1 . . ? C19 C18 H18B 109.1 . . ? H18A C18 H18B 107.8 . . ? C20 C19 C18 114.22(16) . . ? C20 C19 H19A 108.7 . . ? C18 C19 H19A 108.7 . . ? C20 C19 H19B 108.7 . . ? C18 C19 H19B 108.7 . . ? H19A C19 H19B 107.6 . . ? C19 C20 C21 112.12(16) . . ? C19 C20 H20A 109.2 . . ? C21 C20 H20A 109.2 . . ? C19 C20 H20B 109.2 . . ? C21 C20 H20B 109.2 . . ? H20A C20 H20B 107.9 . . ? C20 C21 H21A 109.5 . . ? C20 C21 H21B 109.5 . . ? H21A C21 H21B 109.5 . . ? C20 C21 H21C 109.5 . . ? H21A C21 H21C 109.5 . . ? H21B C21 H21C 109.5 . . ? C1 N1 C5 122.36(15) . . ? C1 N1 H1A 122.2(18) . . ? C5 N1 H1A 115.4(18) . . ? C11 O1 C14 118.30(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 N1 C1 C2 C3 0.5(3) . . . . ? C1 C2 C3 C4 2.2(2) . . . . ? C1 C2 C3 C6 -177.89(16) . . . . ? C2 C3 C4 C5 -2.8(2) . . . . ? C6 C3 C4 C5 177.30(15) . . . . ? C3 C4 C5 N1 0.7(3) . . . . ? C2 C3 C6 C7 -155.65(17) . . . . ? C4 C3 C6 C7 24.2(2) . . . . ? C2 C3 C6 Br2 25.9(2) . . . . ? C4 C3 C6 Br2 -154.22(13) . . . . ? C3 C6 C7 C8 178.80(17) . . . . ? Br2 C6 C7 C8 -2.9(3) . . . . ? C6 C7 C8 C9 -9.6(3) . . . . ? C6 C7 C8 C13 173.07(19) . . . . ? C13 C8 C9 C10 -1.0(3) . . . . ? C7 C8 C9 C10 -178.33(17) . . . . ? C8 C9 C10 C11 0.1(3) . . . . ? C9 C10 C11 O1 -178.96(16) . . . . ? C9 C10 C11 C12 0.4(3) . . . . ? O1 C11 C12 C13 179.44(16) . . . . ? C10 C11 C12 C13 0.1(3) . . . . ? C11 C12 C13 C8 -1.0(3) . . . . ? C9 C8 C13 C12 1.4(3) . . . . ? C7 C8 C13 C12 179.08(16) . . . . ? O1 C14 C15 C16 -64.3(2) . . . . ? C14 C15 C16 C17 -179.91(16) . . . . ? C15 C16 C17 C18 -179.61(16) . . . . ? C16 C17 C18 C19 -175.52(17) . . . . ? C17 C18 C19 C20 173.26(17) . . . . ? C18 C19 C20 C21 -178.06(17) . . . . ? C2 C1 N1 C5 -2.9(3) . . . . ? C4 C5 N1 C1 2.2(3) . . . . ? C10 C11 O1 C14 -0.7(2) . . . . ? C12 C11 O1 C14 179.98(15) . . . . ? C15 C14 O1 C11 -175.47(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 N1 H1A Br1 0.89(3) 2.34(3) 3.1869(15) 161(2) . _diffrn_measured_fraction_theta_max 0.975 _diffrn_reflns_theta_full 30.02 _diffrn_measured_fraction_theta_full 0.975 _refine_diff_density_max 1.393 _refine_diff_density_min -0.740 _refine_diff_density_rms 0.071