# Electronic Supplementary Material (ESI) for Chemical Science # This journal is © The Royal Society of Chemistry 2011 data_global _journal_name_full 'Chemical Science' _journal_coden_cambridge 1475 _journal_year ? _journal_volume ? _journal_page_first ? _publ_contact_author_email deng@brandeis.edu _publ_contact_author_name 'Li Deng' loop_ _publ_author_name 'Keith Bartelson' 'Ravi Singh' 'Bruce Foxman' 'Li Deng' data_kb4_152E _database_code_depnum_ccdc_archive 'CCDC 827937' #TrackingRef '- kb4_152E.cif' _audit_creation_date 10-05-23 _audit_creation_method CRYSTALS_ver_14.01 # start Validation Reply Form: Two Alert B issues _vrf_THETMO1_kb4_152E ; PROBLEM: The value of sine(theta_max)/wavelength is less than 0.575 Calculated sin(theta_max)/wavelength = 0.5550 RESPONSE:The severe disorder in the crystal, as well as overall low crystal quality led to a two-theta maximum of 46 degrees. The THETMO1 CIF check flag corresponds to a two-theta maximum of 48 degrees. The data collection was appropriate to the sample and conditions, and unambiguously establishes thee stereochemistry and absolute configuration of the molecule. ; _vrf_PLAT023_kb4_152E ; PROBLEM: Resolution (too) Low [sin(theta)/Lambda < 0.6].. 23.23 Deg. RESPONSE:The severe disorder in the crystal, as well as overall low crystal quality led to a two-theta maximum of 46 degrees. The CIF check flag corresponds to a two-theta maximum of 48 degrees. The data collection was appropriate to the sample and conditions, and unambiguously establishes thee stereochemistry and absolute configuration of the molecule. ; _vrf_PLAT220_kb4_152E ; PROBLEM: Large Non-Solvent C Ueq(max)/Ueq(min) ... 4.93 Ratio RESPONSE: The 4.93 ratio is between a phenyl C atom (C14) that is part of a badly disordered phenyl ring and a normal ring C atom (e.g., C7). It was not possible to resolve the disorder. ; # end Validation Reply Form _oxford_structure_analysis_title 'KB4_152endo_0m in P2(1)2(1)2(1)' _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 6.6796(4) _cell_length_b 9.2556(6) _cell_length_c 31.8029(19) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 1966.2(2) _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21 ' _symmetry_space_group_name_Hall 'P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz x,y,z x+1/2,-y+1/2,-z -x,y+1/2,-z+1/2 -x+1/2,-y,z+1/2 loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' Br -0.2901 2.4595 17.1789 2.1723 5.2358 16.5796 5.6377 0.2609 3.9851 41.4328 2.9557 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 4 # Given Formula = C19 H24 Br1 N1 O6 # Dc = 1.49 Fooo = 912.00 Mu = 21.26 M = 442.31 # Found Formula = C19 H24 Br1 N1 O6 # Dc = 1.49 FOOO = 912.00 Mu = 21.26 M = 442.31 _chemical_formula_sum 'C19 H24 Br1 N1 O6' _chemical_formula_moiety 'C19 H24 Br1 N1 O6' _chemical_compound_source ? _chemical_formula_weight 442.31 _cell_measurement_reflns_used 7653 _cell_measurement_theta_min 3 _cell_measurement_theta_max 23 _cell_measurement_temperature 120 _exptl_crystal_description 'plate fragment' _exptl_crystal_colour colorless _exptl_crystal_size_min 0.088 _exptl_crystal_size_mid 0.337 _exptl_crystal_size_max 0.698 _exptl_crystal_density_diffrn 1.494 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 912 _exptl_absorpt_coefficient_mu 2.126 # Sheldrick geometric approximatio 0.49 0.83 _exptl_absorpt_correction_type numerical _exptl_absorpt_process_details ; Analytical Absorption (De Meulenaer & Tompa, 1965) ; _exptl_absorpt_correction_T_min 0.49 _exptl_absorpt_correction_T_max 0.83 _diffrn_measurement_device-type 'Bruker Kappa Apex2' _diffrn_measurement_device Area _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method '\f & \w scans' # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'Apex2 (Bruker AXS, 2006)' _computing_cell_refinement 'Apex2 (Bruker AXS, 2006)' _computing_data_reduction 'Apex2 (Bruker AXS, 2006)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time . _diffrn_standards_interval_count . _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 120 _diffrn_reflns_number 23700 _reflns_number_total 2822 _diffrn_reflns_av_R_equivalents 0.037 # Number of reflections without Friedels Law is 2822 # Number of reflections with Friedels Law is 1674 # Theoretical number of reflections is about 1408 _diffrn_reflns_theta_min 1.281 _diffrn_reflns_theta_max 23.234 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 23.234 _diffrn_measured_fraction_theta_full 0.997 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -35 _diffrn_reflns_limit_l_max 35 _reflns_limit_h_min -7 _reflns_limit_h_max 7 _reflns_limit_k_min 0 _reflns_limit_k_max 10 _reflns_limit_l_min 0 _reflns_limit_l_max 35 _oxford_diffrn_Wilson_B_factor 3.78 _oxford_diffrn_Wilson_scale 53.80 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.51 _refine_diff_density_max 0.66 # The current dictionary definitions do not cover the # situation where the reflections used for refinement were # selected by a user-defined sigma threshold # The values actually used during refinement _oxford_reflns_threshold_expression_ref I>-10.0\s(I) _refine_ls_number_reflns 2822 _refine_ls_number_restraints 24 _refine_ls_number_parameters 255 _oxford_refine_ls_R_factor_ref 0.0884 _refine_ls_wR_factor_ref 0.2147 _refine_ls_goodness_of_fit_ref 1.0277 _refine_ls_shift/su_max 0.0124692 _refine_ls_shift/su_mean 0.0027814 # The values computed from all data _oxford_reflns_number_all 2822 _refine_ls_R_factor_all 0.0884 _refine_ls_wR_factor_all 0.2147 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 2545 _refine_ls_R_factor_gt 0.0826 _refine_ls_wR_factor_gt 0.2123 _refine_ls_abs_structure_Flack 0.06(4) _refine_ls_abs_structure_details 'Flack (1983), 0 Friedel-pairs' # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration ad _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_hydrogen_treatment none # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method= Modified Sheldrick w=1/[\s^2^(F^2^) + ( 0.10P)^2^ + 8.85P] ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 ; # Insert your own references if required - in alphabetical order _publ_section_references ; Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M.C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435. Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Bruker Analytical X-ray Systems, Inc., 2006. Apex2, Version 2 User Manual, M86-E01078, Madison, WI. De Meulenaer, J. & Tompa, H. (1965). Acta Cryst. 19, 1014. Flack, H. D. (1983). Acta Cryst. A39, 876-881. Larson, A.C. (1970) Crystallographic Computing, Ed Ahmed, F.R., Munksgaard, Copenhagen, 291-294. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical Crystallography Laboratory, Oxford, UK. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atomsattached to an atom. # ..._refinement_flags_... # . no refinement constraints S special position constraint on site # G rigid group refinement of site R riding atom # D distance or angle restraint on site T thermal displacement constraints # U Uiso or Uij restraint (rigid bond) P partial occupancy constraint 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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _oxford_atom_site_special_shape _atom_site_attached_hydrogens Br10 Br 0.3835(14) 0.0980(4) 0.98323(15) 0.1352 0.5000 Uani . . . . . . . Br11 Br 0.4348(14) 0.1536(8) 0.99152(16) 0.1623 0.5000 Uani . . . . . . . O1 O 0.1895(8) 0.1537(6) 0.66347(18) 0.0446 1.0000 Uani . . . . . . . O2 O 0.4465(6) 0.2549(4) 0.69709(14) 0.0242 1.0000 Uani . . . . . . . O3 O -0.0194(6) 0.4174(6) 0.66207(16) 0.0389 1.0000 Uani . . . . . . . O4 O -0.1123(7) 0.5864(5) 0.74296(18) 0.0385 1.0000 Uani . . . . . . . O5 O 0.1409(7) 0.7042(5) 0.71932(18) 0.0404 1.0000 Uani . . . . . . . O6 O 0.9796(16) 0.3148(11) 0.5787(3) 0.1123 1.0000 Uani D U . . . . . N1 N 0.0569(8) 0.5927(6) 0.72992(18) 0.0276 1.0000 Uani . . . . . . . C1 C 0.5196(9) 0.4010(7) 0.7087(2) 0.0254 1.0000 Uani . . . . . . . C3 C 0.2635(10) 0.2615(8) 0.6784(2) 0.0325 1.0000 Uani . . . . . . . C4 C 0.1766(9) 0.4115(8) 0.6781(2) 0.0294 1.0000 Uani . . . . . . . C5 C 0.3298(10) 0.5043(7) 0.6555(2) 0.0274 1.0000 Uani . . . . . . . C6 C 0.5109(10) 0.4987(7) 0.6719(2) 0.0284 1.0000 Uani . . . . . . . C7 C 0.3803(9) 0.4605(6) 0.7434(2) 0.0214 1.0000 Uani . . . . . . . C8 C 0.1709(9) 0.4525(7) 0.7253(2) 0.0230 1.0000 Uani . . . . . . . C9 C 0.4070(10) 0.3824(7) 0.7852(2) 0.0258 1.0000 Uani . . . . . . . C10 C 0.2750(11) 0.4458(7) 0.8202(2) 0.0318 1.0000 Uani . . . . . . . C11 C 0.3043(13) 0.3699(8) 0.8616(2) 0.0398 1.0000 Uani . . . . . . . C12 C 0.4851(15) 0.3819(10) 0.8822(3) 0.0540 1.0000 Uani . . . . . . . C13 C 0.518(2) 0.3143(15) 0.9195(3) 0.0919 1.0000 Uani . . . . . . . C14 C 0.368(3) 0.2262(17) 0.9360(3) 0.1049 1.0000 Uani . . . . . . . C15 C 0.184(3) 0.2111(14) 0.9164(4) 0.0938 1.0000 Uani . . . . . . . C16 C 0.1574(16) 0.2818(10) 0.8781(3) 0.0614 1.0000 Uani . . . . . . . C18 C 0.880(2) 0.1815(18) 0.5744(5) 0.1303 1.0000 Uani D U . . . . . C17 C 0.699(2) 0.2422(13) 0.5929(4) 0.0989 1.0000 Uani D . . . . . . H31 H -0.0109 0.4112 0.6364 0.0588 1.0000 Uiso R . . . . . . H131 H 0.6360 0.3267 0.9340 0.1096 1.0000 Uiso R . . . . . . H121 H 0.5860 0.4365 0.8705 0.0649 1.0000 Uiso R . . . . . . H102 H 0.3088 0.5470 0.8240 0.0389 1.0000 Uiso R . . . . . . H101 H 0.1356 0.4383 0.8117 0.0389 1.0000 Uiso R . . . . . . H91 H 0.5493 0.3866 0.7934 0.0317 1.0000 Uiso R . . . . . . H92 H 0.3679 0.2818 0.7811 0.0310 1.0000 Uiso R . . . . . . H71 H 0.4103 0.5615 0.7481 0.0259 1.0000 Uiso R . . . . . . H11 H 0.6578 0.3946 0.7199 0.0312 1.0000 Uiso R . . . . . . H81 H 0.0945 0.3781 0.7400 0.0278 1.0000 Uiso R . . . . . . H51 H 0.2985 0.5603 0.6321 0.0333 1.0000 Uiso R . . . . . . H61 H 0.6218 0.5480 0.6615 0.0342 1.0000 Uiso R . . . . . . H161 H 0.0379 0.2700 0.8638 0.0773 1.0000 Uiso R . . . . . . H151 H 0.0818 0.1562 0.9282 0.1170 1.0000 Uiso R . . . . . . C20 C 1.213(4) 0.413(3) 0.5374(8) 0.2331 1.0000 Uani D U . . . . . C19 C 1.142(3) 0.2797(19) 0.5551(5) 0.1734 1.0000 Uani D U . . . . . H171 H 0.5874 0.1801 0.5852 0.1490 1.0000 Uiso R . . . . . . H172 H 0.7123 0.2462 0.6231 0.1491 1.0000 Uiso R . . . . . . H173 H 0.6743 0.3367 0.5821 0.1490 1.0000 Uiso R . . . . . . H191 H 1.2301 0.2482 0.5775 0.2140 1.0000 Uiso R . . . . . . H192 H 1.1355 0.2087 0.5336 0.2140 1.0000 Uiso R . . . . . . H203 H 1.3416 0.4027 0.5275 0.3482 1.0000 Uiso R . . . . . . H201 H 1.2040 0.4853 0.5605 0.3480 1.0000 Uiso R . . . . . . H202 H 1.1167 0.4418 0.5157 0.3481 1.0000 Uiso R . . . . . . H182 H 0.9567 0.1236 0.5932 0.1529 1.0000 Uiso R . . . . . . H181 H 0.8572 0.1295 0.5492 0.1529 1.0000 Uiso R . . . . . . 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 Br10 0.314(9) 0.0603(18) 0.0310(18) 0.0104(13) -0.016(3) 0.008(3) Br11 0.240(6) 0.209(7) 0.038(2) 0.034(3) -0.013(3) -0.056(6) O1 0.037(3) 0.034(3) 0.063(4) -0.024(3) 0.001(3) -0.012(2) O2 0.018(2) 0.016(2) 0.039(3) -0.0020(19) 0.0043(19) 0.0030(18) O3 0.015(2) 0.056(3) 0.045(3) -0.014(3) -0.013(2) 0.009(2) O4 0.014(3) 0.033(3) 0.068(3) 0.001(3) 0.010(2) 0.015(2) O5 0.027(3) 0.019(3) 0.075(4) 0.003(2) 0.003(3) 0.007(2) O6 0.116(7) 0.143(8) 0.078(5) -0.003(5) 0.005(5) -0.017(6) N1 0.022(3) 0.016(3) 0.045(3) -0.001(3) 0.003(3) -0.003(3) C1 0.016(3) 0.016(3) 0.043(4) -0.003(3) -0.004(3) 0.000(3) C3 0.033(4) 0.025(4) 0.040(4) -0.002(3) 0.012(3) 0.006(3) C4 0.010(3) 0.037(4) 0.041(4) -0.010(3) 0.001(3) 0.001(3) C5 0.028(4) 0.018(3) 0.037(4) 0.002(3) 0.002(3) 0.008(3) C6 0.014(3) 0.031(4) 0.040(4) 0.006(3) 0.007(3) 0.004(3) C7 0.016(3) 0.013(3) 0.035(4) -0.002(3) 0.002(3) -0.002(2) C8 0.014(3) 0.015(3) 0.040(4) -0.003(3) 0.003(3) -0.005(2) C9 0.018(3) 0.020(3) 0.039(4) -0.009(3) -0.004(3) 0.001(3) C10 0.032(4) 0.021(3) 0.042(4) -0.002(3) 0.005(3) 0.000(3) C11 0.056(5) 0.030(4) 0.033(4) -0.007(3) 0.012(4) 0.004(4) C12 0.071(6) 0.051(5) 0.040(5) -0.005(4) 0.000(5) -0.004(5) C13 0.133(11) 0.098(9) 0.045(6) -0.001(6) -0.005(7) 0.015(9) C14 0.168(15) 0.113(11) 0.034(6) 0.024(7) -0.003(8) 0.038(12) C15 0.152(13) 0.084(8) 0.045(6) 0.013(6) 0.034(8) -0.020(9) C16 0.074(7) 0.056(6) 0.054(5) -0.002(5) 0.027(5) -0.012(5) C18 0.158(13) 0.132(12) 0.101(10) -0.026(9) -0.014(10) -0.083(10) C17 0.157(13) 0.065(7) 0.075(8) 0.020(7) 0.007(9) -0.029(9) C20 0.240(19) 0.28(2) 0.175(17) 0.000(18) 0.020(16) -0.03(2) C19 0.187(14) 0.254(17) 0.079(9) -0.021(11) 0.050(10) -0.009(14) _refine_ls_extinction_coef 390(70) _refine_ls_extinction_method 'Larson (1970), Equation 22' _oxford_refine_ls_scale 0.1961(5) loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag Br10 . C14 . 1.917(12) yes Br11 . C14 . 1.942(12) yes O1 . C3 . 1.210(9) yes O2 . C1 . 1.485(7) yes O2 . C3 . 1.361(8) yes O3 . C4 . 1.406(8) yes O3 . H31 . 0.820 no O4 . N1 . 1.205(7) yes O5 . N1 . 1.222(7) yes O6 . C18 . 1.409(15) yes O6 . C19 . 1.358(15) yes N1 . C8 . 1.511(8) yes C1 . C6 . 1.479(10) yes C1 . C7 . 1.546(9) yes C1 . H11 . 0.991 no C3 . C4 . 1.505(10) yes C4 . C5 . 1.517(10) yes C4 . C8 . 1.550(9) yes C5 . C6 . 1.319(10) yes C5 . H51 . 0.929 no C6 . H61 . 0.932 no C7 . C8 . 1.515(9) yes C7 . C9 . 1.523(9) yes C7 . H71 . 0.967 no C8 . H81 . 0.975 no C9 . C10 . 1.536(9) yes C9 . H91 . 0.986 no C9 . H92 . 0.975 no C10 . C11 . 1.505(11) yes C10 . H102 . 0.971 no C10 . H101 . 0.972 no C11 . C12 . 1.379(12) yes C11 . C16 . 1.380(12) yes C12 . C13 . 1.358(14) yes C12 . H121 . 0.921 no C13 . C14 . 1.40(2) yes C13 . H131 . 0.920 no C14 . C15 . 1.39(2) yes C15 . C16 . 1.392(16) yes C15 . H151 . 0.930 no C16 . H161 . 0.925 no C18 . C17 . 1.456(17) yes C18 . H182 . 0.954 no C18 . H181 . 0.948 no C17 . H171 . 0.971 no C17 . H172 . 0.965 no C17 . H173 . 0.955 no C20 . C19 . 1.44(2) yes C20 . H203 . 0.920 no C20 . H201 . 0.994 no C20 . H202 . 0.980 no C19 . H191 . 0.971 no C19 . H192 . 0.948 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C1 . O2 . C3 . 111.3(5) yes C4 . O3 . H31 . 107.1 no C18 . O6 . C19 . 96.6(8) yes O5 . N1 . O4 . 124.5(6) yes O5 . N1 . C8 . 117.8(5) yes O4 . N1 . C8 . 117.7(5) yes O2 . C1 . C6 . 110.3(5) yes O2 . C1 . C7 . 107.7(5) yes C6 . C1 . C7 . 108.8(5) yes O2 . C1 . H11 . 110.0 no C6 . C1 . H11 . 110.9 no C7 . C1 . H11 . 109.0 no O2 . C3 . O1 . 120.1(6) yes O2 . C3 . C4 . 113.0(6) yes O1 . C3 . C4 . 126.9(7) yes C3 . C4 . O3 . 113.4(6) yes C3 . C4 . C5 . 105.4(5) yes O3 . C4 . C5 . 115.8(6) yes C3 . C4 . C8 . 103.3(6) yes O3 . C4 . C8 . 108.6(5) yes C5 . C4 . C8 . 109.7(5) yes C4 . C5 . C6 . 114.0(6) yes C4 . C5 . H51 . 122.9 no C6 . C5 . H51 . 123.1 no C1 . C6 . C5 . 112.0(6) yes C1 . C6 . H61 . 123.4 no C5 . C6 . H61 . 124.6 no C1 . C7 . C8 . 105.5(5) yes C1 . C7 . C9 . 112.5(5) yes C8 . C7 . C9 . 114.6(5) yes C1 . C7 . H71 . 109.2 no C8 . C7 . H71 . 107.3 no C9 . C7 . H71 . 107.5 no C4 . C8 . C7 . 111.0(5) yes C4 . C8 . N1 . 108.5(5) yes C7 . C8 . N1 . 112.7(5) yes C4 . C8 . H81 . 107.6 no C7 . C8 . H81 . 109.6 no N1 . C8 . H81 . 107.3 no C7 . C9 . C10 . 112.5(5) yes C7 . C9 . H91 . 108.9 no C10 . C9 . H91 . 110.2 no C7 . C9 . H92 . 107.9 no C10 . C9 . H92 . 107.9 no H91 . C9 . H92 . 109.3 no C9 . C10 . C11 . 112.4(6) yes C9 . C10 . H102 . 109.0 no C11 . C10 . H102 . 108.2 no C9 . C10 . H101 . 108.7 no C11 . C10 . H101 . 109.6 no H102 . C10 . H101 . 109.0 no C10 . C11 . C12 . 119.5(7) yes C10 . C11 . C16 . 121.0(8) yes C12 . C11 . C16 . 119.3(8) yes C11 . C12 . C13 . 121.3(11) yes C11 . C12 . H121 . 119.5 no C13 . C12 . H121 . 119.2 no C12 . C13 . C14 . 118.7(12) yes C12 . C13 . H131 . 121.3 no C14 . C13 . H131 . 120.0 no Br10 . C14 . Br11 . 20.1(3) yes Br10 . C14 . C13 . 128.1(12) yes Br11 . C14 . C13 . 112.2(12) yes Br10 . C14 . C15 . 109.9(13) yes Br11 . C14 . C15 . 125.4(13) yes C13 . C14 . C15 . 121.8(10) yes C14 . C15 . C16 . 117.3(12) yes C14 . C15 . H151 . 121.5 no C16 . C15 . H151 . 121.2 no C15 . C16 . C11 . 121.3(11) yes C15 . C16 . H161 . 118.9 no C11 . C16 . H161 . 119.7 no O6 . C18 . C17 . 91.0(11) yes O6 . C18 . H182 . 100.1 no C17 . C18 . H182 . 114.3 no O6 . C18 . H181 . 127.0 no C17 . C18 . H181 . 114.1 no H182 . C18 . H181 . 109.2 no C18 . C17 . H171 . 107.8 no C18 . C17 . H172 . 109.9 no H171 . C17 . H172 . 110.2 no C18 . C17 . H173 . 110.4 no H171 . C17 . H173 . 108.6 no H172 . C17 . H173 . 109.9 no C19 . C20 . H203 . 110.5 no C19 . C20 . H201 . 105.6 no H203 . C20 . H201 . 112.3 no C19 . C20 . H202 . 106.8 no H203 . C20 . H202 . 113.6 no H201 . C20 . H202 . 107.5 no C20 . C19 . O6 . 105.9(9) yes C20 . C19 . H191 . 110.1 no O6 . C19 . H191 . 98.6 no C20 . C19 . H192 . 109.3 no O6 . C19 . H192 . 121.9 no H191 . C19 . H192 . 110.3 no