# Electronic Supplementary Material (ESI) for CrystEngComm # 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_5Br _cell_length_a 8.1302(2) _cell_length_b 11.0677(4) _cell_length_c 17.3238(7) _cell_angle_alpha 90 _cell_angle_beta 95.2468(12) _cell_angle_gamma 90 _cell_volume 1552.31(9) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1 ' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z -x,y+1/2,-z+1/2 x,-y+1/2,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' Cl 0.1484 0.1585 11.4604 0.0104 7.1964 1.1662 6.2556 18.5194 1.6455 47.7784 -9.5574 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 2 # Given Formula = C27 H32 Br2 Cl2 N4 O1 # Dc = 1.41 Fooo = 704.00 Mu = 28.08 M = 329.65 # Found Formula = C28 H36 Br2 Cl2 N4 O2 # Dc = 1.48 FOOO = 704.00 Mu = 28.14 M = 345.67 _chemical_formula_sum 'C28 H36 Br2 Cl2 N4 O2' _chemical_formula_moiety 'C26 H28 Cl2 N4, 2 (C H4 O), 2(Br)' _chemical_compound_source synthesized _chemical_formula_weight 691.33 _cell_measurement_reflns_used 3321 _cell_measurement_theta_min 5 _cell_measurement_theta_max 27 _cell_measurement_temperature 150 _exptl_crystal_description shard _exptl_crystal_colour colourless _exptl_crystal_size_min 0.100 _exptl_crystal_size_mid 0.160 _exptl_crystal_size_max 0.900 _exptl_crystal_density_diffrn 1.479 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 704 _exptl_absorpt_coefficient_mu 2.814 # Sheldrick geometric approximatio 0.64 0.75 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _exptl_absorpt_correction_T_min 0.896 _exptl_absorpt_correction_T_max 1.00 # For a Kappa CCD, set Tmin to 1.0 and # Tmax to the ratio of max:min frame scales in scale_all.log _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_device Area _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method \w # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'COLLECT (Nonius, 2001).' _computing_cell_refinement 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _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 'Crystal Maker (Crystal Maker Software Ltd.)' _audit_creation_method 'CRYSTALS (Betteridge et al., 2003)' _diffrn_standards_interval_time . _diffrn_standards_interval_count . _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 150 _diffrn_reflns_number 14129 _reflns_number_total 3526 _diffrn_reflns_av_R_equivalents 0.035 _diffrn_reflns_theta_min 5.113 _diffrn_reflns_theta_max 27.488 _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 25.289 _diffrn_measured_fraction_theta_full 0.990 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _reflns_limit_h_min -10 _reflns_limit_h_max 10 _reflns_limit_k_min 0 _reflns_limit_k_max 14 _reflns_limit_l_min 0 _reflns_limit_l_max 22 _oxford_diffrn_Wilson_B_factor 2.43 _oxford_diffrn_Wilson_scale 10.06 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.44 _refine_diff_density_max 0.64 # 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>-3.0\s(I) _refine_ls_number_reflns 2583 _refine_ls_number_restraints 0 _refine_ls_number_parameters 172 _oxford_refine_ls_R_factor_ref 0.0470 _refine_ls_wR_factor_ref 0.0863 _refine_ls_goodness_of_fit_ref 0.9195 _refine_ls_shift/su_max 0.0007345 _refine_ls_shift/su_mean 0.0000221 # The values computed from all data _oxford_reflns_number_all 2583 _refine_ls_R_factor_all 0.0470 _refine_ls_wR_factor_all 0.0863 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 2234 _refine_ls_R_factor_gt 0.0379 _refine_ls_wR_factor_gt 0.0809 # 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 . _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_hydrogen_treatment constr # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 15.8 22.4 11.2 3.05 ; # 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 Br1 Br 0.01897(4) 0.86945(4) 0.70838(2) 0.0325 1.0000 Uani . . . . . . . Cl2 Cl 0.69229(9) 0.51224(8) 0.68775(5) 0.0270 1.0000 Uani . . . . . . . C3 C 0.5147(4) 0.5740(3) 0.64285(19) 0.0235 1.0000 Uani . . . . . . . N4 N 0.5005(3) 0.6817(3) 0.60911(16) 0.0237 1.0000 Uani . . . . . . . C5 C 0.3357(4) 0.7005(3) 0.5829(2) 0.0279 1.0000 Uani . . . . . . . C6 C 0.2519(4) 0.6010(3) 0.6021(2) 0.0270 1.0000 Uani . . . . . . . N7 N 0.3669(4) 0.5217(3) 0.63889(16) 0.0252 1.0000 Uani . . . . . . . C8 C 0.3291(5) 0.4022(3) 0.6695(2) 0.0301 1.0000 Uani . . . . . . . C9 C 0.2840(4) 0.3102(3) 0.6064(2) 0.0254 1.0000 Uani . . . . . . . C10 C 0.3442(4) 0.3162(3) 0.5333(2) 0.0269 1.0000 Uani . . . . . . . C11 C 0.3072(4) 0.2279(3) 0.4787(2) 0.0262 1.0000 Uani . . . . . . . C12 C 0.3641(5) 0.2321(3) 0.3974(2) 0.0298 1.0000 Uani . . . . . . . C13 C 0.2101(4) 0.1291(3) 0.4969(2) 0.0275 1.0000 Uani . . . . . . . C14 C 0.1493(5) 0.1231(3) 0.5686(2) 0.0315 1.0000 Uani . . . . . . . C15 C 0.1843(5) 0.2132(3) 0.6231(2) 0.0315 1.0000 Uani . . . . . . . C16 C 0.0715(5) 0.5745(4) 0.5956(2) 0.0398 1.0000 Uani . . . . . . . C17 C 0.2790(5) 0.8171(4) 0.5473(2) 0.0397 1.0000 Uani . . . . . . . O18 O 0.3587(4) 0.7175(3) 0.76468(17) 0.0479 1.0000 Uani . . . . . . . C19 C 0.3228(7) 0.6550(5) 0.8311(3) 0.0613 1.0000 Uani . . . . . . . H81 H 0.4279 0.3742 0.7022 0.0354 1.0000 Uiso R . . . . . . H82 H 0.2377 0.4116 0.7019 0.0358 1.0000 Uiso R . . . . . . H101 H 0.4094 0.3826 0.5213 0.0335 1.0000 Uiso R . . . . . . H121 H 0.4037 0.1532 0.3844 0.0364 1.0000 Uiso R . . . . . . H122 H 0.2732 0.2566 0.3597 0.0355 1.0000 Uiso R . . . . . . H131 H 0.1876 0.0687 0.4599 0.0328 1.0000 Uiso R . . . . . . H141 H 0.0835 0.0573 0.5800 0.0377 1.0000 Uiso R . . . . . . H151 H 0.1401 0.2101 0.6713 0.0370 1.0000 Uiso R . . . . . . H161 H 0.0538 0.4987 0.5686 0.0589 1.0000 Uiso R . . . . . . H162 H 0.0359 0.5698 0.6468 0.0592 1.0000 Uiso R . . . . . . H163 H 0.0147 0.6389 0.5674 0.0589 1.0000 Uiso R . . . . . . H171 H 0.1639 0.8099 0.5278 0.0603 1.0000 Uiso R . . . . . . H172 H 0.2868 0.8803 0.5875 0.0602 1.0000 Uiso R . . . . . . H173 H 0.3452 0.8418 0.5051 0.0599 1.0000 Uiso R . . . . . . H192 H 0.2958 0.7116 0.8701 0.0923 1.0000 Uiso R . . . . . . H193 H 0.4196 0.6101 0.8493 0.0920 1.0000 Uiso R . . . . . . H191 H 0.2317 0.6013 0.8185 0.0921 1.0000 Uiso R . . . . . . H181 H 0.2722 0.7548 0.7518 0.0720 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 Br1 0.0255(2) 0.0430(2) 0.0298(2) -0.00360(17) 0.00607(14) -0.00490(17) Cl2 0.0154(4) 0.0282(4) 0.0374(5) 0.0038(4) 0.0019(3) 0.0006(3) C3 0.0185(16) 0.0296(19) 0.0229(17) -0.0002(15) 0.0044(13) 0.0024(14) N4 0.0224(14) 0.0256(15) 0.0239(14) -0.0005(12) 0.0070(12) -0.0016(12) C5 0.0264(18) 0.033(2) 0.0245(17) -0.0014(15) 0.0054(14) 0.0031(15) C6 0.0234(17) 0.035(2) 0.0224(17) -0.0058(15) 0.0037(14) 0.0046(15) N7 0.0262(15) 0.0256(16) 0.0250(14) -0.0020(12) 0.0080(12) -0.0025(12) C8 0.0328(19) 0.031(2) 0.0278(18) 0.0002(16) 0.0089(15) -0.0050(16) C9 0.0219(17) 0.0257(18) 0.0287(18) 0.0008(15) 0.0029(14) -0.0028(15) C10 0.0270(18) 0.0234(18) 0.0309(18) 0.0003(15) 0.0057(15) -0.0041(15) C11 0.0246(17) 0.0259(19) 0.0289(18) 0.0024(15) 0.0064(14) 0.0008(15) C12 0.0311(19) 0.0250(19) 0.034(2) -0.0027(15) 0.0057(15) -0.0068(16) C13 0.0286(18) 0.0222(17) 0.0315(18) -0.0014(15) 0.0016(15) -0.0037(15) C14 0.0298(19) 0.0269(19) 0.038(2) 0.0044(17) 0.0051(16) -0.0072(16) C15 0.0298(19) 0.033(2) 0.0337(19) 0.0034(16) 0.0119(16) -0.0020(16) C16 0.0242(19) 0.054(3) 0.042(2) -0.006(2) 0.0046(17) 0.0022(18) C17 0.038(2) 0.042(2) 0.040(2) 0.0080(19) 0.0093(18) 0.0122(19) O18 0.0516(18) 0.0513(19) 0.0406(16) -0.0055(14) 0.0036(14) 0.0074(15) C19 0.070(3) 0.066(4) 0.048(3) 0.011(2) 0.005(2) -0.014(3) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.3149(3) 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 Cl2 . C3 . 1.718(3) yes C3 . N4 . 1.328(5) yes C3 . N7 . 1.330(4) yes N4 . C12 2_666 1.469(4) yes N4 . C5 . 1.390(5) yes C5 . C6 . 1.353(5) yes C5 . C17 . 1.485(5) yes C6 . N7 . 1.394(5) yes C6 . C16 . 1.489(5) yes N7 . C8 . 1.468(5) yes C8 . C9 . 1.515(5) yes C8 . H81 . 0.989 no C8 . H82 . 0.977 no C9 . C10 . 1.401(5) yes C9 . C15 . 1.392(5) yes C10 . C11 . 1.374(5) yes C10 . H101 . 0.941 no C11 . C12 . 1.522(5) yes C11 . C13 . 1.401(5) yes C12 . H121 . 0.965 no C12 . H122 . 0.979 no C13 . C14 . 1.379(5) yes C13 . H131 . 0.934 no C14 . C15 . 1.385(5) yes C14 . H141 . 0.935 no C15 . H151 . 0.938 no C16 . H161 . 0.965 no C16 . H162 . 0.960 no C16 . H163 . 0.959 no C17 . H171 . 0.968 no C17 . H172 . 0.985 no C17 . H173 . 0.985 no O18 . C19 . 1.397(6) yes O18 . H181 . 0.828 no C19 . H192 . 0.961 no C19 . H193 . 0.960 no C19 . H191 . 0.959 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 Cl2 . C3 . N4 . 126.3(3) yes Cl2 . C3 . N7 . 124.6(3) yes N4 . C3 . N7 . 109.0(3) yes C12 2_666 N4 . C3 . 125.6(3) yes C12 2_666 N4 . C5 . 125.7(3) yes C3 . N4 . C5 . 108.7(3) yes N4 . C5 . C6 . 106.8(3) yes N4 . C5 . C17 . 121.3(3) yes C6 . C5 . C17 . 131.7(3) yes C5 . C6 . N7 . 107.1(3) yes C5 . C6 . C16 . 131.1(4) yes N7 . C6 . C16 . 121.6(3) yes C6 . N7 . C3 . 108.3(3) yes C6 . N7 . C8 . 125.4(3) yes C3 . N7 . C8 . 126.3(3) yes N7 . C8 . C9 . 112.9(3) yes N7 . C8 . H81 . 107.6 no C9 . C8 . H81 . 109.4 no N7 . C8 . H82 . 107.9 no C9 . C8 . H82 . 109.9 no H81 . C8 . H82 . 109.0 no C8 . C9 . C10 . 122.7(3) yes C8 . C9 . C15 . 118.4(3) yes C10 . C9 . C15 . 118.9(3) yes C9 . C10 . C11 . 121.1(3) yes C9 . C10 . H101 . 119.1 no C11 . C10 . H101 . 119.8 no C10 . C11 . C12 . 123.3(3) yes C10 . C11 . C13 . 119.5(3) yes C12 . C11 . C13 . 117.3(3) yes C11 . C12 . N4 2_666 112.6(3) yes C11 . C12 . H121 . 108.9 no N4 2_666 C12 . H121 . 107.6 no C11 . C12 . H122 . 110.5 no N4 2_666 C12 . H122 . 107.1 no H121 . C12 . H122 . 110.0 no C11 . C13 . C14 . 119.8(3) yes C11 . C13 . H131 . 118.8 no C14 . C13 . H131 . 121.4 no C13 . C14 . C15 . 120.7(3) yes C13 . C14 . H141 . 119.2 no C15 . C14 . H141 . 120.1 no C9 . C15 . C14 . 120.1(3) yes C9 . C15 . H151 . 119.4 no C14 . C15 . H151 . 120.6 no C6 . C16 . H161 . 108.0 no C6 . C16 . H162 . 108.7 no H161 . C16 . H162 . 110.9 no C6 . C16 . H163 . 108.5 no H161 . C16 . H163 . 110.9 no H162 . C16 . H163 . 109.8 no C5 . C17 . H171 . 109.1 no C5 . C17 . H172 . 109.1 no H171 . C17 . H172 . 107.6 no C5 . C17 . H173 . 112.2 no H171 . C17 . H173 . 109.9 no H172 . C17 . H173 . 108.8 no C19 . O18 . H181 . 103.4 no O18 . C19 . H192 . 109.6 no O18 . C19 . H193 . 107.4 no H192 . C19 . H193 . 109.9 no O18 . C19 . H191 . 109.5 no H192 . C19 . H191 . 110.1 no H193 . C19 . H191 . 110.3 no loop_ _geom_hbond_atom_site_label_D _geom_hbond_site_symmetry_D _geom_hbond_atom_site_label_H _geom_hbond_site_symmetry_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_angle_DHA _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_publ_flag C8 . H81 . O18 3_646 150 0.99 2.48 3.375(5) yes _database_code_depnum_ccdc_archive 'CCDC 963237' ####################################################################### # # 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_6Br _cell_length_a 8.70900(10) _cell_length_b 8.97990(10) _cell_length_c 26.0376(3) _cell_angle_alpha 89.5146(4) _cell_angle_beta 84.8630(4) _cell_angle_gamma 85.5213(5) _cell_volume 2021.92(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 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' 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' I -0.4742 1.8119 20.1472 4.3470 18.9949 0.3814 7.5138 27.7660 2.2735 66.8776 4.0712 'International Tables Vol C 4.2.6.8 and 6.1.1.4' S 0.1246 0.1234 6.9053 1.4679 5.2034 22.2151 1.4379 0.2536 1.5863 56.1720 0.8669 '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' _cell_formula_units_Z 2 # Given Formula = C26 H28 Br2 I2 N4 O4 S1 # Dc = 2.23 Fooo = 1028.00 Mu = 54.18 M = 1359.32 # Found Formula = C21.33 H30.67 Br1.33 I1.33 N2.67 O2 S2 # Dc = 1.72 FOOO = 1028.00 Mu = 37.22 M = 1044.56 _chemical_formula_sum 'C32 H46 Br2 I2 N4 O3 S3' _chemical_formula_moiety 'C26 H28 I2 N4, 3(C2 H6 O S), 2(Br)' _chemical_compound_source synthesized _chemical_formula_weight 1044.54 _cell_measurement_reflns_used 8237 _cell_measurement_theta_min 5 _cell_measurement_theta_max 27 _cell_measurement_temperature 150 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_min 0.030 _exptl_crystal_size_mid 0.180 _exptl_crystal_size_max 0.260 _exptl_crystal_density_diffrn 1.716 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 1028 _exptl_absorpt_coefficient_mu 3.722 # Sheldrick geometric approximatio 0.51 0.89 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _exptl_absorpt_correction_T_min 0.896 _exptl_absorpt_correction_T_max 1.00 # For a Kappa CCD, set Tmin to 1.0 and # Tmax to the ratio of max:min frame scales in scale_all.log _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_device Area _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method \w # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'COLLECT (Nonius, 2001).' _computing_cell_refinement 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _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 'Crystal Maker (Crystal Maker Software Ltd.)' _audit_creation_method 'CRYSTALS (Betteridge et al., 2003)' _diffrn_standards_interval_time . _diffrn_standards_interval_count . _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 150 _diffrn_reflns_number 32968 _reflns_number_total 9210 _diffrn_reflns_av_R_equivalents 0.056 _diffrn_reflns_theta_min 5.102 _diffrn_reflns_theta_max 27.495 _diffrn_measured_fraction_theta_max 0.990 _diffrn_reflns_theta_full 26.670 _diffrn_measured_fraction_theta_full 0.992 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -33 _diffrn_reflns_limit_l_max 33 _reflns_limit_h_min -11 _reflns_limit_h_max 11 _reflns_limit_k_min -11 _reflns_limit_k_max 11 _reflns_limit_l_min 0 _reflns_limit_l_max 33 _oxford_diffrn_Wilson_B_factor 1.95 _oxford_diffrn_Wilson_scale 26.78 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_diff_density_min -1.28 _refine_diff_density_max 2.17 # 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>-3.0\s(I) _refine_ls_number_reflns 8317 _refine_ls_number_restraints 0 _refine_ls_number_parameters 415 _oxford_refine_ls_R_factor_ref 0.0529 _refine_ls_wR_factor_ref 0.1121 _refine_ls_goodness_of_fit_ref 0.9631 _refine_ls_shift/su_max 0.0010653 _refine_ls_shift/su_mean 0.0000257 # The values computed with all filters except I/sigma _oxford_reflns_number_all 8317 _refine_ls_R_factor_all 0.0529 _refine_ls_wR_factor_all 0.1121 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 6909 _refine_ls_R_factor_gt 0.0427 _refine_ls_wR_factor_gt 0.1023 # 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 . _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_hydrogen_treatment constr #undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 21.5 31.3 15.3 4.01 ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atoms attached 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 _atom_site_attached_hydrogens I1 I 0.30529(4) 1.36165(4) 0.462468(13) 0.0242 1.0000 Uani . . . . . . C2 C 0.4877(6) 1.2888(5) 0.50675(19) 0.0212 1.0000 Uani . . . . . . N3 N 0.6372(5) 1.2578(5) 0.48840(16) 0.0211 1.0000 Uani . . . . . . C4 C 0.7001(6) 1.2712(6) 0.43441(19) 0.0241 1.0000 Uani . . . . . . C5 C 0.7556(6) 1.1222(6) 0.40984(19) 0.0234 1.0000 Uani . . . . . . C6 C 0.6795(6) 0.9924(6) 0.42025(19) 0.0231 1.0000 Uani . . . . . . C7 C 0.7310(6) 0.8596(6) 0.39526(18) 0.0222 1.0000 Uani . . . . . . C8 C 0.8597(7) 0.8564(6) 0.35862(19) 0.0267 1.0000 Uani . . . . . . C9 C 0.9339(6) 0.9860(6) 0.3480(2) 0.0277 1.0000 Uani . . . . . . C10 C 0.8839(6) 1.1175(6) 0.37369(19) 0.0249 1.0000 Uani . . . . . . C11 C 0.6604(6) 0.7134(6) 0.4073(2) 0.0249 1.0000 Uani . . . . . . N12 N 0.5188(5) 0.7284(5) 0.44202(16) 0.0229 1.0000 Uani . . . . . . C13 C 0.3725(6) 0.7726(6) 0.4270(2) 0.0264 1.0000 Uani . . . . . . C14 C 0.7261(6) 1.2202(6) 0.5288(2) 0.0259 1.0000 Uani . . . . . . C15 C 0.8955(7) 1.1875(8) 0.5211(2) 0.0360 1.0000 Uani . . . . . . C16 C 0.3421(8) 0.7946(8) 0.3725(2) 0.0403 1.0000 Uani . . . . . . I17 I -0.18433(4) 0.35053(4) 0.950479(13) 0.0265 1.0000 Uani . . . . . . Br18 Br 0.43427(6) 0.52899(5) 0.11943(2) 0.0250 1.0000 Uani . . . . . . C19 C -0.0076(6) 0.2889(5) 0.99845(19) 0.0218 1.0000 Uani . . . . . . N20 N -0.0218(5) 0.2767(5) 1.05017(16) 0.0226 1.0000 Uani . . . . . . C21 C 0.1218(6) 0.2411(6) 1.0681(2) 0.0253 1.0000 Uani . . . . . . C22 C 0.2257(6) 0.2323(6) 1.0261(2) 0.0269 1.0000 Uani . . . . . . N23 N 0.1442(5) 0.2619(5) 0.98342(17) 0.0237 1.0000 Uani . . . . . . C24 C 0.2138(6) 0.2656(6) 0.9300(2) 0.0254 1.0000 Uani . . . . . . C25 C 0.2656(6) 0.1121(5) 0.90885(19) 0.0210 1.0000 Uani . . . . . . C26 C 0.1898(6) -0.0159(6) 0.92341(19) 0.0229 1.0000 Uani . . . . . . C27 C 0.2378(6) -0.1530(6) 0.90097(19) 0.0226 1.0000 Uani . . . . . . C28 C 0.1682(6) -0.2970(6) 0.9174(2) 0.0261 1.0000 Uani . . . . . . C29 C 0.3626(6) -0.1623(6) 0.86299(19) 0.0254 1.0000 Uani . . . . . . C30 C 0.4396(6) -0.0370(6) 0.8491(2) 0.0287 1.0000 Uani . . . . . . C31 C 0.3937(6) 0.0989(6) 0.87200(19) 0.0243 1.0000 Uani . . . . . . C32 C 0.3983(7) 0.2045(7) 1.0217(2) 0.0369 1.0000 Uani . . . . . . C33 C 0.1445(8) 0.2271(8) 1.1240(2) 0.0384 1.0000 Uani . . . . . . Br35 Br 0.05582(5) 0.49010(5) 0.39204(2) 0.0236 1.0000 Uani . . . . . . S36 S 0.24298(18) 0.52483(18) 0.78283(6) 0.0349 1.0000 Uani . . . . . . O37 O 0.1266(6) 0.4624(5) 0.82175(17) 0.0437 1.0000 Uani . . . . . . C38 C 0.3525(9) 0.3716(9) 0.7514(3) 0.0512 1.0000 Uani . . . . . . C39 C 0.1391(9) 0.5915(11) 0.7304(3) 0.0576 1.0000 Uani . . . . . . S40 S 0.1671(2) 0.86868(19) 0.20133(6) 0.0422 1.0000 Uani . . . . . . O41 O 0.2170(6) 0.9782(6) 0.2380(2) 0.0565 1.0000 Uani . . . . . . C42 C -0.0386(9) 0.8923(9) 0.2048(3) 0.0494 1.0000 Uani . . . . . . C43 C 0.1776(9) 0.6923(9) 0.2332(3) 0.0551 1.0000 Uani . . . . . . S44 S 0.42253(19) 0.25011(19) 0.32160(6) 0.0391 1.0000 Uani . . . . . . O45 O 0.5212(6) 0.3753(6) 0.33097(17) 0.0460 1.0000 Uani . . . . . . C46 C 0.5457(8) 0.1129(8) 0.2855(2) 0.0422 1.0000 Uani . . . . . . C47 C 0.3102(9) 0.3108(8) 0.2698(3) 0.0499 1.0000 Uani . . . . . . H41 H 0.7784 1.3393 0.4318 0.0258 1.0000 Uiso R . . . . . H42 H 0.6176 1.3097 0.4160 0.0253 1.0000 Uiso R . . . . . H61 H 0.5885 1.0012 0.4410 0.0251 1.0000 Uiso R . . . . . H81 H 0.8910 0.7710 0.3399 0.0297 1.0000 Uiso R . . . . . H91 H 1.0196 0.9817 0.3239 0.0322 1.0000 Uiso R . . . . . H101 H 0.9332 1.2014 0.3664 0.0260 1.0000 Uiso R . . . . . H111 H 0.7353 0.6494 0.4262 0.0306 1.0000 Uiso R . . . . . H112 H 0.6356 0.6643 0.3752 0.0295 1.0000 Uiso R . . . . . H153 H 0.9299 1.1332 0.5506 0.0488 1.0000 Uiso R . . . . . H152 H 0.9433 1.2818 0.5176 0.0485 1.0000 Uiso R . . . . . H151 H 0.9181 1.1275 0.4899 0.0482 1.0000 Uiso R . . . . . H161 H 0.2417 0.8488 0.3697 0.0616 1.0000 Uiso R . . . . . H162 H 0.3420 0.6931 0.3584 0.0621 1.0000 Uiso R . . . . . H163 H 0.4224 0.8461 0.3531 0.0619 1.0000 Uiso R . . . . . H241 H 0.1373 0.3063 0.9098 0.0241 1.0000 Uiso R . . . . . H242 H 0.2980 0.3285 0.9279 0.0259 1.0000 Uiso R . . . . . H261 H 0.1003 -0.0037 0.9459 0.0293 1.0000 Uiso R . . . . . H281 H 0.1445 -0.3522 0.8872 0.0352 1.0000 Uiso R . . . . . H282 H 0.2390 -0.3554 0.9359 0.0331 1.0000 Uiso R . . . . . H291 H 0.3929 -0.2513 0.8469 0.0320 1.0000 Uiso R . . . . . H301 H 0.5203 -0.0473 0.8238 0.0301 1.0000 Uiso R . . . . . H311 H 0.4439 0.1790 0.8627 0.0274 1.0000 Uiso R . . . . . H321 H 0.4305 0.1482 0.9891 0.0539 1.0000 Uiso R . . . . . H322 H 0.4323 0.1472 1.0507 0.0542 1.0000 Uiso R . . . . . H323 H 0.4448 0.3021 1.0207 0.0530 1.0000 Uiso R . . . . . H333 H 0.2444 0.1752 1.1311 0.0595 1.0000 Uiso R . . . . . H332 H 0.0633 0.1724 1.1410 0.0587 1.0000 Uiso R . . . . . H331 H 0.1401 0.3260 1.1392 0.0590 1.0000 Uiso R . . . . . H421 H -0.0757 0.8242 0.1819 0.0600 1.0000 Uiso R . . . . . H422 H -0.0801 0.8738 0.2390 0.0600 1.0000 Uiso R . . . . . H423 H -0.0698 0.9917 0.1952 0.0600 1.0000 Uiso R . . . . . H431 H 0.1468 0.6185 0.2112 0.0670 1.0000 Uiso R . . . . . H432 H 0.1109 0.6974 0.2642 0.0670 1.0000 Uiso R . . . . . H433 H 0.2808 0.6669 0.2411 0.0670 1.0000 Uiso R . . . . . H381 H 0.4274 0.4074 0.7265 0.0613 1.0000 Uiso R . . . . . H382 H 0.2852 0.3132 0.7348 0.0613 1.0000 Uiso R . . . . . H383 H 0.4032 0.3120 0.7761 0.0613 1.0000 Uiso R . . . . . H391 H 0.2084 0.6322 0.7047 0.0710 1.0000 Uiso R . . . . . H392 H 0.0922 0.5111 0.7161 0.0710 1.0000 Uiso R . . . . . H393 H 0.0614 0.6666 0.7422 0.0710 1.0000 Uiso R . . . . . H471 H 0.2452 0.2352 0.2622 0.0608 1.0000 Uiso R . . . . . H472 H 0.2485 0.3996 0.2796 0.0608 1.0000 Uiso R . . . . . H473 H 0.3775 0.3300 0.2401 0.0608 1.0000 Uiso R . . . . . H461 H 0.4881 0.0309 0.2786 0.0524 1.0000 Uiso R . . . . . H462 H 0.6293 0.0793 0.3048 0.0524 1.0000 Uiso R . . . . . H463 H 0.5848 0.1551 0.2539 0.0524 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 I1 0.02253(17) 0.02321(17) 0.02697(17) -0.00055(12) -0.00173(12) -0.00284(12) C2 0.023(2) 0.017(2) 0.024(2) -0.0024(18) -0.0008(19) -0.0041(18) N3 0.021(2) 0.019(2) 0.022(2) -0.0006(15) 0.0033(16) -0.0044(16) C4 0.027(3) 0.022(2) 0.023(2) 0.0007(19) 0.0043(19) -0.008(2) C5 0.024(2) 0.026(3) 0.020(2) 0.0018(19) -0.0027(19) 0.001(2) C6 0.022(2) 0.025(2) 0.022(2) -0.0002(19) 0.0006(19) -0.0015(19) C7 0.023(2) 0.025(3) 0.019(2) 0.0020(18) -0.0022(18) -0.0046(19) C8 0.034(3) 0.027(3) 0.019(2) -0.0021(19) -0.001(2) -0.003(2) C9 0.025(3) 0.032(3) 0.025(2) 0.002(2) 0.006(2) -0.005(2) C10 0.027(3) 0.025(3) 0.024(2) 0.0044(19) -0.001(2) -0.009(2) C11 0.025(3) 0.025(3) 0.024(2) -0.0032(19) 0.0052(19) -0.005(2) N12 0.026(2) 0.022(2) 0.021(2) -0.0023(16) 0.0009(17) -0.0066(17) C13 0.027(3) 0.026(3) 0.026(3) -0.001(2) -0.002(2) -0.004(2) C14 0.028(3) 0.021(2) 0.029(3) -0.005(2) -0.002(2) -0.004(2) C15 0.027(3) 0.048(4) 0.033(3) -0.005(3) -0.004(2) 0.000(3) C16 0.036(3) 0.058(4) 0.029(3) 0.003(3) -0.005(2) -0.006(3) I17 0.02639(18) 0.02277(17) 0.03051(18) 0.00162(13) -0.00219(13) -0.00281(13) Br18 0.0184(2) 0.0199(2) 0.0382(3) 0.0020(2) -0.0100(2) -0.00195(18) C19 0.022(2) 0.017(2) 0.026(2) -0.0015(18) -0.0007(19) -0.0014(18) N20 0.024(2) 0.019(2) 0.024(2) -0.0011(16) 0.0034(17) -0.0026(16) C21 0.027(3) 0.019(2) 0.031(3) -0.001(2) -0.004(2) -0.004(2) C22 0.029(3) 0.023(2) 0.030(3) 0.000(2) -0.002(2) -0.006(2) N23 0.024(2) 0.020(2) 0.027(2) -0.0001(16) 0.0023(17) -0.0068(17) C24 0.026(3) 0.023(3) 0.026(3) 0.002(2) 0.003(2) -0.006(2) C25 0.021(2) 0.019(2) 0.023(2) -0.0004(18) -0.0017(18) -0.0033(18) C26 0.022(2) 0.025(3) 0.022(2) -0.0007(19) 0.0033(19) -0.0049(19) C27 0.022(2) 0.023(2) 0.023(2) -0.0002(19) -0.0018(19) -0.0037(19) C28 0.027(3) 0.023(2) 0.028(3) -0.004(2) 0.003(2) -0.003(2) C29 0.029(3) 0.025(3) 0.022(2) -0.0024(19) 0.003(2) -0.003(2) C30 0.025(3) 0.035(3) 0.026(3) -0.006(2) 0.006(2) -0.007(2) C31 0.026(3) 0.028(3) 0.020(2) 0.0025(19) 0.0004(19) -0.012(2) C32 0.029(3) 0.042(3) 0.041(3) -0.007(3) -0.005(2) 0.000(2) C33 0.045(4) 0.044(3) 0.028(3) 0.004(2) -0.005(2) -0.013(3) Br35 0.0160(2) 0.0206(2) 0.0354(3) -0.00139(19) -0.00938(19) -0.00067(18) S36 0.0389(8) 0.0391(8) 0.0292(7) -0.0016(6) -0.0068(6) -0.0134(6) O37 0.050(3) 0.050(3) 0.031(2) -0.0022(19) 0.0034(19) -0.014(2) C38 0.050(4) 0.056(4) 0.047(4) 0.000(3) 0.008(3) -0.010(3) C39 0.041(4) 0.085(6) 0.049(4) 0.029(4) -0.014(3) -0.014(4) S40 0.0463(9) 0.0424(9) 0.0380(8) -0.0016(6) 0.0082(7) -0.0169(7) O41 0.049(3) 0.059(3) 0.064(3) -0.012(3) 0.000(2) -0.027(3) C42 0.051(4) 0.053(4) 0.048(4) 0.010(3) -0.014(3) -0.019(3) C43 0.049(4) 0.046(4) 0.069(5) 0.004(4) 0.008(4) -0.006(3) S44 0.0400(8) 0.0486(9) 0.0294(7) 0.0035(6) 0.0004(6) -0.0124(7) O45 0.047(3) 0.060(3) 0.034(2) -0.002(2) -0.0043(19) -0.020(2) C46 0.042(4) 0.052(4) 0.032(3) 0.005(3) -0.008(3) 0.003(3) C47 0.048(4) 0.044(4) 0.060(4) 0.001(3) -0.021(3) -0.002(3) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.23832(15) 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 I1 . Br35 1_565 3.1145(6) yes I1 . C2 . 2.106(5) yes C2 . N12 2_676 1.338(6) yes C2 . N3 . 1.354(6) yes N3 . C4 . 1.470(6) yes N3 . C14 . 1.386(7) yes C4 . C5 . 1.513(7) yes C4 . H41 . 0.949 no C4 . H42 . 0.942 no C5 . C6 . 1.398(7) yes C5 . C10 . 1.393(7) yes C6 . C7 . 1.387(7) yes C6 . H61 . 0.917 no C7 . C8 . 1.404(7) yes C7 . C11 . 1.511(7) yes C8 . C9 . 1.389(7) yes C8 . H81 . 0.923 no C9 . C10 . 1.382(8) yes C9 . H91 . 0.931 no C10 . H101 . 0.906 no C11 . N12 . 1.461(6) yes C11 . H111 . 0.996 no C11 . H112 . 0.997 no N12 . C13 . 1.393(7) yes C13 . C14 2_676 1.372(7) yes C13 . C16 . 1.475(8) yes C14 . C15 . 1.478(8) yes C15 . H153 . 0.964 no C15 . H152 . 0.973 no C15 . H151 . 0.975 no C16 . H161 . 0.975 no C16 . H162 . 0.986 no C16 . H163 . 0.971 no I17 . Br18 2_566 3.0871(6) yes I17 . C19 . 2.106(5) yes C19 . N20 . 1.346(7) yes C19 . N23 . 1.348(6) yes N20 . C28 2_557 1.465(6) yes N20 . C21 . 1.387(7) yes C21 . C22 . 1.356(8) yes C21 . C33 . 1.489(8) yes C22 . N23 . 1.383(7) yes C22 . C32 . 1.498(8) yes N23 . C24 . 1.467(6) yes C24 . C25 . 1.510(7) yes C24 . H241 . 0.937 no C24 . H242 . 0.958 no C25 . C26 . 1.402(7) yes C25 . C31 . 1.403(7) yes C26 . C27 . 1.386(7) yes C26 . H261 . 0.932 no C27 . C28 . 1.513(7) yes C27 . C29 . 1.400(7) yes C28 . H281 . 0.979 no C28 . H282 . 0.941 no C29 . C30 . 1.383(7) yes C29 . H291 . 0.915 no C30 . C31 . 1.377(8) yes C30 . H301 . 0.920 no C31 . H311 . 0.892 no C32 . H321 . 1.000 no C32 . H322 . 0.965 no C32 . H323 . 0.993 no C33 . H333 . 0.986 no C33 . H332 . 0.965 no C33 . H331 . 0.972 no S36 . O37 . 1.504(5) yes S36 . C38 . 1.774(8) yes S36 . C39 . 1.780(7) yes C38 . H381 . 0.950 no C38 . H382 . 0.950 no C38 . H383 . 0.950 no C39 . H391 . 0.950 no C39 . H392 . 0.950 no C39 . H393 . 0.950 no S40 . O41 . 1.492(5) yes S40 . C42 . 1.782(8) yes S40 . C43 . 1.782(8) yes C42 . H421 . 0.950 no C42 . H422 . 0.950 no C42 . H423 . 0.950 no C43 . H431 . 0.950 no C43 . H432 . 0.950 no C43 . H433 . 0.950 no S44 . O45 . 1.501(5) yes S44 . C46 . 1.784(7) yes S44 . C47 . 1.793(7) yes C46 . H461 . 0.950 no C46 . H462 . 0.950 no C46 . H463 . 0.950 no C47 . H471 . 0.950 no C47 . H472 . 0.950 no C47 . H473 . 0.950 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 Br35 1_565 I1 . C2 . 174.70(13) yes I1 . C2 . N12 2_676 127.3(4) yes I1 . C2 . N3 . 125.7(4) yes N12 2_676 C2 . N3 . 106.9(4) yes C2 . N3 . C4 . 125.9(4) yes C2 . N3 . C14 . 109.8(4) yes C4 . N3 . C14 . 124.1(4) yes N3 . C4 . C5 . 113.1(4) yes N3 . C4 . H41 . 110.2 no C5 . C4 . H41 . 112.0 no N3 . C4 . H42 . 106.5 no C5 . C4 . H42 . 105.9 no H41 . C4 . H42 . 108.9 no C4 . C5 . C6 . 122.7(4) yes C4 . C5 . C10 . 117.9(5) yes C6 . C5 . C10 . 119.3(5) yes C5 . C6 . C7 . 120.7(5) yes C5 . C6 . H61 . 117.5 no C7 . C6 . H61 . 121.4 no C6 . C7 . C8 . 119.5(5) yes C6 . C7 . C11 . 123.2(4) yes C8 . C7 . C11 . 117.2(4) yes C7 . C8 . C9 . 119.6(5) yes C7 . C8 . H81 . 120.6 no C9 . C8 . H81 . 119.7 no C8 . C9 . C10 . 120.8(5) yes C8 . C9 . H91 . 118.4 no C10 . C9 . H91 . 120.8 no C5 . C10 . C9 . 120.1(5) yes C5 . C10 . H101 . 120.0 no C9 . C10 . H101 . 119.9 no C7 . C11 . N12 . 113.8(4) yes C7 . C11 . H111 . 107.5 no N12 . C11 . H111 . 105.2 no C7 . C11 . H112 . 111.0 no N12 . C11 . H112 . 107.5 no H111 . C11 . H112 . 111.7 no C11 . N12 . C2 2_676 124.9(4) yes C11 . N12 . C13 . 124.8(4) yes C2 2_676 N12 . C13 . 110.1(4) yes N12 . C13 . C14 2_676 106.4(5) yes N12 . C13 . C16 . 122.6(5) yes C14 2_676 C13 . C16 . 130.8(5) yes N3 . C14 . C13 2_676 106.7(5) yes N3 . C14 . C15 . 122.4(5) yes C13 2_676 C14 . C15 . 130.8(5) yes C14 . C15 . H153 . 109.0 no C14 . C15 . H152 . 108.3 no H153 . C15 . H152 . 110.2 no C14 . C15 . H151 . 107.6 no H153 . C15 . H151 . 110.6 no H152 . C15 . H151 . 111.1 no C13 . C16 . H161 . 111.0 no C13 . C16 . H162 . 105.1 no H161 . C16 . H162 . 109.8 no C13 . C16 . H163 . 112.3 no H161 . C16 . H163 . 109.8 no H162 . C16 . H163 . 108.6 no Br18 2_566 I17 . C19 . 174.63(13) yes I17 . C19 . N20 . 127.1(4) yes I17 . C19 . N23 . 126.5(4) yes N20 . C19 . N23 . 106.4(4) yes C28 2_557 N20 . C19 . 124.7(4) yes C28 2_557 N20 . C21 . 125.1(4) yes C19 . N20 . C21 . 110.2(4) yes N20 . C21 . C22 . 106.4(5) yes N20 . C21 . C33 . 122.8(5) yes C22 . C21 . C33 . 130.7(5) yes C21 . C22 . N23 . 107.1(5) yes C21 . C22 . C32 . 130.6(5) yes N23 . C22 . C32 . 122.2(5) yes C22 . N23 . C19 . 109.8(4) yes C22 . N23 . C24 . 124.7(4) yes C19 . N23 . C24 . 125.4(5) yes N23 . C24 . C25 . 112.8(4) yes N23 . C24 . H241 . 107.3 no C25 . C24 . H241 . 106.9 no N23 . C24 . H242 . 109.5 no C25 . C24 . H242 . 110.9 no H241 . C24 . H242 . 109.2 no C24 . C25 . C26 . 123.1(4) yes C24 . C25 . C31 . 117.8(4) yes C26 . C25 . C31 . 119.0(4) yes C25 . C26 . C27 . 120.7(4) yes C25 . C26 . H261 . 117.8 no C27 . C26 . H261 . 121.2 no C26 . C27 . C28 . 123.4(4) yes C26 . C27 . C29 . 119.1(5) yes C28 . C27 . C29 . 117.4(4) yes C27 . C28 . N20 2_557 114.4(4) yes C27 . C28 . H281 . 110.4 no N20 2_557 C28 . H281 . 105.2 no C27 . C28 . H282 . 109.0 no N20 2_557 C28 . H282 . 107.9 no H281 . C28 . H282 . 109.8 no C27 . C29 . C30 . 120.4(5) yes C27 . C29 . H291 . 120.0 no C30 . C29 . H291 . 119.6 no C29 . C30 . C31 . 120.6(5) yes C29 . C30 . H301 . 117.8 no C31 . C30 . H301 . 121.6 no C25 . C31 . C30 . 120.1(5) yes C25 . C31 . H311 . 120.1 no C30 . C31 . H311 . 119.8 no C22 . C32 . H321 . 108.0 no C22 . C32 . H322 . 111.1 no H321 . C32 . H322 . 109.6 no C22 . C32 . H323 . 108.8 no H321 . C32 . H323 . 110.1 no H322 . C32 . H323 . 109.3 no C21 . C33 . H333 . 113.9 no C21 . C33 . H332 . 109.3 no H333 . C33 . H332 . 107.8 no C21 . C33 . H331 . 109.5 no H333 . C33 . H331 . 107.2 no H332 . C33 . H331 . 109.1 no O37 . S36 . C38 . 107.6(3) yes O37 . S36 . C39 . 106.4(3) yes C38 . S36 . C39 . 98.5(4) yes S36 . C38 . H381 . 109.6 no S36 . C38 . H382 . 109.2 no H381 . C38 . H382 . 109.5 no S36 . C38 . H383 . 109.5 no H381 . C38 . H383 . 109.5 no H382 . C38 . H383 . 109.5 no S36 . C39 . H391 . 109.4 no S36 . C39 . H392 . 109.4 no H391 . C39 . H392 . 109.5 no S36 . C39 . H393 . 109.6 no H391 . C39 . H393 . 109.5 no H392 . C39 . H393 . 109.5 no O41 . S40 . C42 . 106.7(3) yes O41 . S40 . C43 . 106.1(4) yes C42 . S40 . C43 . 96.0(4) yes S40 . C42 . H421 . 109.6 no S40 . C42 . H422 . 109.5 no H421 . C42 . H422 . 109.5 no S40 . C42 . H423 . 109.4 no H421 . C42 . H423 . 109.5 no H422 . C42 . H423 . 109.5 no S40 . C43 . H431 . 109.2 no S40 . C43 . H432 . 109.7 no H431 . C43 . H432 . 109.5 no S40 . C43 . H433 . 109.5 no H431 . C43 . H433 . 109.5 no H432 . C43 . H433 . 109.5 no O45 . S44 . C46 . 106.1(3) yes O45 . S44 . C47 . 106.0(3) yes C46 . S44 . C47 . 96.3(3) yes S44 . C46 . H461 . 109.2 no S44 . C46 . H462 . 109.6 no H461 . C46 . H462 . 109.5 no S44 . C46 . H463 . 109.6 no H461 . C46 . H463 . 109.5 no H462 . C46 . H463 . 109.5 no S44 . C47 . H471 . 109.6 no S44 . C47 . H472 . 109.4 no H471 . C47 . H472 . 109.5 no S44 . C47 . H473 . 109.4 no H471 . C47 . H473 . 109.5 no H472 . C47 . H473 . 109.5 no loop_ _geom_hbond_atom_site_label_D _geom_hbond_site_symmetry_D _geom_hbond_atom_site_label_H _geom_hbond_site_symmetry_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_angle_DHA _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_publ_flag C4 . H42 . O45 1_565 147.89(17) 0.942 2.486 3.322(8) yes C28 . H281 . O37 1_545 165.60(18) 0.979 2.415 3.372(8) yes C38 . H381 . O45 2_666 142.2(2) 0.950 2.493 3.296(8) yes C39 . H391 . O45 2_666 144.2(2) 0.950 2.450 3.268(8) yes C47 . H471 . O41 1_545 149.3(2) 0.950 2.434 3.287(8) yes _database_code_depnum_ccdc_archive 'CCDC 963238' ####################################################################### # # 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_1NO3 #============================================================================== # start Validation Reply Form _vrf_PLAT431_1 ; PROBLEM: Short Inter HL..A Contact Br1 .. O17 .. 2.72 Ang. RESPONSE: This is a halogen-bonding interaction. ; _cell_length_a 8.7552(2) _cell_length_b 9.1778(2) _cell_length_c 19.3962(5) _cell_angle_alpha 100.8354(10) _cell_angle_beta 95.9931(10) _cell_angle_gamma 95.4914(11) _cell_volume 1511.75(6) _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 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 2 # Given Formula = C26 H32 Br2 N6 O8 # Dc = 1.57 Fooo = 718.00 Mu = 27.38 M = 716.38 # Found Formula = C26 H31 Br2 N6 O7.50 # Dc = 1.55 FOOO = 718.00 Mu = 27.36 M = 707.38 _chemical_formula_sum 'C26 H31 Br2 N6 O7.5' _chemical_formula_moiety 'C26 H28 Br2 N4, 2(N O3), 1.5(H2 O)' _chemical_compound_source synthesized _chemical_formula_weight 707.38 _cell_measurement_reflns_used 6324 _cell_measurement_theta_min 1 _cell_measurement_theta_max 27 _cell_measurement_temperature 150 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_min 0.080 _exptl_crystal_size_mid 0.180 _exptl_crystal_size_max 0.220 _exptl_crystal_density_diffrn 1.554 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 718 _exptl_absorpt_coefficient_mu 2.736 # Sheldrick geometric approximatio 0.61 0.80 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _exptl_absorpt_correction_T_min 0.913 _exptl_absorpt_correction_T_max 1.00 # For a Kappa CCD, set Tmin to 1.0 and # Tmax to the ratio of max:min frame scales in scale_all.log _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_device Area _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method \w # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'COLLECT (Nonius, 2001).' _computing_cell_refinement 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _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 'Crystal Maker (Crystal Maker Software Ltd.)' _audit_creation_method 'CRYSTALS (Betteridge et al., 2003)' _diffrn_standards_interval_time . _diffrn_standards_interval_count . _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 150 _diffrn_reflns_number 23830 _reflns_number_total 6931 _diffrn_reflns_av_R_equivalents 0.040 _diffrn_reflns_theta_min 2.155 _diffrn_reflns_theta_max 27.528 _diffrn_measured_fraction_theta_max 0.993 _diffrn_reflns_theta_full 26.977 _diffrn_measured_fraction_theta_full 0.998 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 25 _reflns_limit_h_min -11 _reflns_limit_h_max 11 _reflns_limit_k_min -11 _reflns_limit_k_max 11 _reflns_limit_l_min 0 _reflns_limit_l_max 25 _oxford_diffrn_Wilson_B_factor 2.73 _oxford_diffrn_Wilson_scale 25.96 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -1.08 _refine_diff_density_max 1.93 # 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>-3.0\s(I) _refine_ls_number_reflns 6907 _refine_ls_number_restraints 0 _refine_ls_number_parameters 380 _oxford_refine_ls_R_factor_ref 0.0994 _refine_ls_wR_factor_ref 0.2173 _refine_ls_goodness_of_fit_ref 0.9691 _refine_ls_shift/su_max 0.0002020 _refine_ls_shift/su_mean 0.0000113 # The values computed from all data _oxford_reflns_number_all 6907 _refine_ls_R_factor_all 0.0994 _refine_ls_wR_factor_all 0.2173 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 4657 _refine_ls_R_factor_gt 0.0658 _refine_ls_wR_factor_gt 0.1669 # 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 . _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_hydrogen_treatment constr # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 16.0 23.7 11.0 2.77 ; # 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 Br1 Br -0.19822(7) -0.33813(7) 0.03311(4) 0.0355 1.0000 Uani . . . . . . . Br2 Br 0.63955(7) -0.31597(7) 0.53689(4) 0.0358 1.0000 Uani . . . . . . . O3 O -0.0202(11) 0.5933(11) 0.1921(5) 0.0952 1.0000 Uani . . . . . . . N5 N 0.4282(9) -0.2664(8) 0.4110(4) 0.0523 1.0000 Uani . . . . . . . N6 N -0.4487(7) -0.4482(7) 0.1483(3) 0.0391 1.0000 Uani . . . . . . . C7 C 0.1255(10) -0.2348(9) -0.1022(4) 0.0486 1.0000 Uani . . . . . . . C8 C 0.1539(13) -0.2085(12) -0.1713(5) 0.0677 1.0000 Uani . . . . . . . O9 O -0.5568(8) -0.4379(8) 0.1863(4) 0.0703 1.0000 Uani . . . . . . . C10 C -0.2350(10) -0.1681(9) -0.1492(4) 0.0491 1.0000 Uani . . . . . . . O11 O 0.9779(13) 0.4901(12) 0.3254(6) 0.1187 1.0000 Uani . . . . . . . N12 N 0.1339(8) -0.2590(7) 0.0102(3) 0.0457 1.0000 Uani . . . . . . . C13 C 0.2236(10) -0.2272(9) -0.0419(4) 0.0478 1.0000 Uani . . . . . . . C14 C -0.3608(10) -0.1875(10) -0.2013(4) 0.0498 1.0000 Uani . . . . . . . O15 O -0.3348(10) -0.5071(9) 0.1678(5) 0.0845 1.0000 Uani . . . . . . . O16 O 1.2083(17) 0.4262(12) 0.3188(5) 0.1201 1.0000 Uani . . . . . . . O17 O -0.4578(9) -0.3989(10) 0.0937(4) 0.0822 1.0000 Uani . . . . . . . C18 C 0.6392(9) -0.0206(9) 0.3933(4) 0.0477 1.0000 Uani . . . . . . . O19 O 0.6813(18) 0.4184(16) 0.3042(8) 0.0707 0.5000 Uani . . . . . . . N20 N -0.0227(8) -0.2736(7) -0.0852(3) 0.0460 1.0000 Uani . . . . . . . C21 C 0.1633(11) 0.0598(10) 0.7096(5) 0.0544 1.0000 Uani . . . . . . . C22 C 0.2702(11) -0.2586(10) 0.5743(4) 0.0533 1.0000 Uani . . . . . . . C23 C 0.2041(10) -0.2276(10) 0.4485(4) 0.0505 1.0000 Uani . . . . . . . C24 C 0.3955(11) -0.2021(11) -0.0289(5) 0.0589 1.0000 Uani . . . . . . . N25 N 1.0961(11) 0.4347(10) 0.3505(4) 0.0697 1.0000 Uani . . . . . . . C26 C 0.6411(10) -0.1618(9) 0.3527(4) 0.0489 1.0000 Uani . . . . . . . N27 N 0.3062(8) -0.2569(7) 0.5026(3) 0.0456 1.0000 Uani . . . . . . . C29 C 0.2531(10) -0.0981(9) 0.1233(4) 0.0479 1.0000 Uani . . . . . . . C30 C 0.3831(10) -0.0767(10) 0.1741(4) 0.0503 1.0000 Uani . . . . . . . C31 C -0.1621(11) -0.3040(9) -0.1370(5) 0.0559 1.0000 Uani . . . . . . . C32 C 0.1641(10) -0.0808(10) 0.6682(4) 0.0507 1.0000 Uani . . . . . . . O33 O 1.0909(9) 0.4016(9) 0.4093(4) 0.0796 1.0000 Uani . . . . . . . C34 C 0.1973(10) -0.2552(9) 0.0836(4) 0.0484 1.0000 Uani . . . . . . . C35 C 0.4425(10) -0.2765(9) 0.4793(5) 0.0487 1.0000 Uani . . . . . . . C36 C 0.0414(11) -0.2072(12) 0.4586(6) 0.0647 1.0000 Uani . . . . . . . C37 C 0.5439(11) -0.2989(10) 0.3632(5) 0.0569 1.0000 Uani . . . . . . . C38 C -0.0144(9) -0.2868(8) -0.0175(4) 0.0462 1.0000 Uani . . . . . . . C39 C 0.2812(10) -0.2346(10) 0.3914(5) 0.0528 1.0000 Uani . . . . . . . C40 C -0.1831(9) -0.0241(9) -0.1109(4) 0.0480 1.0000 Uani . . . . . . . C41 C -0.4358(10) -0.0683(10) -0.2131(5) 0.0549 1.0000 Uani . . . . . . . C42 C 0.2654(9) -0.1011(9) 0.6170(4) 0.0468 1.0000 Uani . . . . . . . C43 C 0.2318(14) -0.2105(14) 0.3198(5) 0.0744 1.0000 Uani . . . . . . . H82 H 0.0847 -0.1408 -0.1860 0.1061 1.0000 Uiso R . . . . . . H81 H 0.1385 -0.3025 -0.2049 0.1060 1.0000 Uiso R . . . . . . H83 H 0.2602 -0.1646 -0.1665 0.1060 1.0000 Uiso R . . . . . . H141 H -0.3944 -0.2828 -0.2292 0.0619 1.0000 Uiso R . . . . . . H181 H 0.5733 -0.0081 0.4286 0.0578 1.0000 Uiso R . . . . . . H221 H 0.3481 -0.3068 0.5984 0.0618 1.0000 Uiso R . . . . . . H222 H 0.1690 -0.3151 0.5715 0.0620 1.0000 Uiso R . . . . . . H241 H 0.4270 -0.1192 0.0105 0.0892 1.0000 Uiso R . . . . . . H242 H 0.4346 -0.2908 -0.0174 0.0891 1.0000 Uiso R . . . . . . H243 H 0.4360 -0.1793 -0.0708 0.0891 1.0000 Uiso R . . . . . . H301 H 0.4359 -0.1582 0.1818 0.0630 1.0000 Uiso R . . . . . . H311 H -0.1345 -0.3563 -0.1822 0.0661 1.0000 Uiso R . . . . . . H312 H -0.2381 -0.3699 -0.1204 0.0660 1.0000 Uiso R . . . . . . H341 H 0.2840 -0.3150 0.0836 0.0610 1.0000 Uiso R . . . . . . H342 H 0.1154 -0.2979 0.1073 0.0610 1.0000 Uiso R . . . . . . H362 H -0.0089 -0.1835 0.4162 0.0970 1.0000 Uiso R . . . . . . H361 H -0.0108 -0.2981 0.4675 0.0971 1.0000 Uiso R . . . . . . H363 H 0.0394 -0.1268 0.4981 0.0971 1.0000 Uiso R . . . . . . H371 H 0.6114 -0.3642 0.3820 0.0679 1.0000 Uiso R . . . . . . H372 H 0.4893 -0.3517 0.3176 0.0681 1.0000 Uiso R . . . . . . H401 H -0.0980 -0.0093 -0.0759 0.0580 1.0000 Uiso R . . . . . . H411 H -0.5213 -0.0823 -0.2481 0.0670 1.0000 Uiso R . . . . . . H432 H 0.1218 -0.2059 0.3139 0.1120 1.0000 Uiso R . . . . . . H431 H 0.2562 -0.2914 0.2854 0.1121 1.0000 Uiso R . . . . . . H433 H 0.2852 -0.1182 0.3134 0.1120 1.0000 Uiso R . . . . . . H31 H 0.0204 0.5594 0.2258 0.1462 1.0000 Uiso R . . . . . . H32 H -0.1119 0.5544 0.1882 0.1461 1.0000 Uiso R . . . . . . H191 H 0.7747 0.4484 0.3108 0.1070 0.5000 Uiso R . . . . . . H192 H 0.6566 0.4110 0.2537 0.1070 0.5000 Uiso R . . . . . . H321 H 0.0959 -0.1625 0.6748 0.0630 1.0000 Uiso R . . . . . . C1 C 0.7417(10) -0.1809(10) 0.2999(4) 0.0507 1.0000 Uani . . . . . . . H211 H 0.0959 0.0722 0.7450 0.0650 1.0000 Uiso R . . . . . . H11 H 0.7431 -0.2765 0.2710 0.0659 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 Br1 0.0312(3) 0.0329(3) 0.0415(4) 0.0056(3) 0.0019(3) 0.0052(2) Br2 0.0324(4) 0.0268(3) 0.0457(4) 0.0058(3) 0.0019(3) -0.0021(2) O3 0.088(6) 0.108(7) 0.092(6) 0.032(5) 0.000(5) 0.007(5) N5 0.058(4) 0.047(4) 0.050(4) 0.007(3) 0.011(3) -0.005(3) N6 0.035(3) 0.038(3) 0.045(3) 0.014(3) 0.000(2) 0.003(2) C7 0.053(5) 0.041(4) 0.050(4) 0.010(3) -0.003(4) 0.008(3) C8 0.084(7) 0.073(6) 0.047(5) 0.019(4) -0.001(5) 0.008(5) O9 0.071(4) 0.066(4) 0.073(4) 0.014(3) 0.018(4) -0.004(3) C10 0.050(4) 0.050(4) 0.043(4) 0.004(3) -0.005(3) 0.006(3) O11 0.116(8) 0.117(8) 0.113(7) 0.047(6) -0.054(6) -0.012(6) N12 0.049(4) 0.043(3) 0.044(3) 0.007(3) 0.001(3) 0.010(3) C13 0.052(4) 0.042(4) 0.050(4) 0.011(3) 0.008(3) 0.009(3) C14 0.048(4) 0.053(4) 0.045(4) 0.007(3) -0.004(3) 0.004(3) O15 0.081(5) 0.086(5) 0.089(5) 0.026(4) -0.005(4) 0.029(4) O16 0.181(11) 0.109(8) 0.077(6) 0.013(5) 0.049(7) 0.027(7) O17 0.069(5) 0.114(6) 0.074(5) 0.038(5) 0.012(4) 0.020(4) C18 0.042(4) 0.051(4) 0.049(4) 0.011(3) 0.008(3) -0.001(3) O19 0.082(10) 0.069(9) 0.069(9) 0.026(7) 0.018(7) 0.019(7) N20 0.051(4) 0.040(3) 0.044(3) 0.006(3) -0.005(3) 0.008(3) C21 0.056(5) 0.062(5) 0.049(4) 0.015(4) 0.015(4) 0.010(4) C22 0.054(5) 0.054(5) 0.050(4) 0.014(4) 0.004(4) -0.003(4) C23 0.056(5) 0.049(4) 0.045(4) 0.011(3) 0.001(3) 0.002(4) C24 0.055(5) 0.065(6) 0.057(5) 0.017(4) 0.008(4) -0.002(4) N25 0.079(6) 0.072(5) 0.049(4) 0.015(4) -0.015(4) -0.014(4) C26 0.050(4) 0.051(4) 0.045(4) 0.011(3) 0.006(3) 0.000(3) N27 0.046(3) 0.046(3) 0.045(3) 0.009(3) 0.008(3) 0.004(3) C29 0.050(4) 0.052(4) 0.041(4) 0.010(3) 0.002(3) 0.002(3) C30 0.054(5) 0.051(4) 0.047(4) 0.013(3) 0.003(3) 0.010(4) C31 0.060(5) 0.042(4) 0.059(5) 0.002(4) -0.009(4) 0.009(4) C32 0.060(5) 0.050(4) 0.043(4) 0.012(3) 0.005(3) 0.008(4) O33 0.073(5) 0.098(6) 0.069(4) 0.040(4) -0.006(4) -0.013(4) C34 0.052(4) 0.043(4) 0.047(4) 0.006(3) -0.004(3) 0.006(3) C35 0.051(4) 0.039(4) 0.055(5) 0.010(3) 0.009(4) -0.005(3) C36 0.055(5) 0.067(6) 0.070(6) 0.013(5) 0.001(4) 0.008(4) C37 0.058(5) 0.047(4) 0.062(5) 0.002(4) 0.017(4) -0.004(4) C38 0.050(4) 0.036(4) 0.050(4) 0.004(3) -0.003(3) 0.007(3) C39 0.051(5) 0.049(4) 0.056(5) 0.007(4) 0.007(4) 0.003(4) C40 0.043(4) 0.053(4) 0.046(4) 0.007(3) -0.006(3) 0.013(3) C41 0.050(5) 0.062(5) 0.050(5) 0.013(4) -0.006(4) 0.006(4) C42 0.051(4) 0.047(4) 0.044(4) 0.019(3) 0.001(3) 0.000(3) C43 0.080(7) 0.085(7) 0.057(6) 0.022(5) 0.001(5) -0.003(6) C1 0.051(4) 0.052(5) 0.044(4) 0.003(3) 0.004(3) 0.000(4) _refine_ls_extinction_coef 280(20) _refine_ls_extinction_method 'Larson (1970), Equation 22' _oxford_refine_ls_scale 0.2098(3) 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 Br1 . C38 . 2.033(9) yes Br2 . C35 . 2.056(9) yes O3 . H31 . 0.835 no O3 . H32 . 0.837 no N5 . C35 . 1.338(11) yes N5 . C37 . 1.458(11) yes N5 . C39 . 1.377(11) yes N6 . O9 . 1.258(9) yes N6 . O15 . 1.237(9) yes N6 . O17 . 1.226(9) yes C7 . C8 . 1.448(12) yes C7 . C13 . 1.363(11) yes C7 . N20 . 1.401(11) yes C8 . H82 . 0.967 no C8 . H81 . 0.967 no C8 . H83 . 0.966 no C10 . C14 . 1.389(11) yes C10 . C31 . 1.501(11) yes C10 . C40 . 1.397(11) yes O11 . N25 . 1.286(13) yes N12 . C13 . 1.399(10) yes N12 . C34 . 1.466(10) yes N12 . C38 . 1.333(10) yes C13 . C24 . 1.488(12) yes C14 . C41 . 1.371(12) yes C14 . H141 . 0.940 no O16 . N25 . 1.213(14) yes C18 . C42 2_656 1.387(11) yes C18 . C26 . 1.387(12) yes C18 . H181 . 0.938 no O19 . H191 . 0.826 no O19 . H192 . 0.968 no N20 . C31 . 1.466(10) yes N20 . C38 . 1.338(10) yes C21 . C1 2_656 1.375(12) yes C21 . C32 . 1.387(12) yes C21 . H211 . 0.950 no C22 . N27 . 1.461(10) yes C22 . C42 . 1.531(12) yes C22 . H221 . 0.974 no C22 . H222 . 0.973 no C23 . N27 . 1.388(10) yes C23 . C36 . 1.483(13) yes C23 . C39 . 1.350(12) yes C24 . H241 . 0.968 no C24 . H242 . 0.967 no C24 . H243 . 0.969 no N25 . O33 . 1.238(11) yes C26 . C37 . 1.509(11) yes C26 . C1 . 1.417(12) yes N27 . C35 . 1.336(10) yes C29 . C40 2_555 1.376(11) yes C29 . C30 . 1.399(11) yes C29 . C34 . 1.509(11) yes C30 . C41 2_555 1.410(12) yes C30 . H301 . 0.942 no C31 . H311 . 0.982 no C31 . H312 . 0.976 no C32 . C42 . 1.398(12) yes C32 . H321 . 0.950 no C34 . H341 . 0.979 no C34 . H342 . 0.981 no C36 . H362 . 0.962 no C36 . H361 . 0.966 no C36 . H363 . 0.962 no C37 . H371 . 0.973 no C37 . H372 . 0.976 no C39 . C43 . 1.474(13) yes C40 . H401 . 0.935 no C41 . H411 . 0.938 no C43 . H432 . 0.964 no C43 . H431 . 0.957 no C43 . H433 . 0.963 no C1 . H11 . 0.950 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 H31 . O3 . H32 . 101.4 no C35 . N5 . C37 . 125.4(8) yes C35 . N5 . C39 . 109.1(7) yes C37 . N5 . C39 . 125.2(8) yes O9 . N6 . O15 . 118.6(7) yes O9 . N6 . O17 . 119.7(7) yes O15 . N6 . O17 . 121.7(8) yes C8 . C7 . C13 . 131.4(9) yes C8 . C7 . N20 . 123.0(8) yes C13 . C7 . N20 . 105.6(7) yes C7 . C8 . H82 . 109.7 no C7 . C8 . H81 . 109.3 no H82 . C8 . H81 . 110.4 no C7 . C8 . H83 . 106.5 no H82 . C8 . H83 . 110.5 no H81 . C8 . H83 . 110.2 no C14 . C10 . C31 . 117.9(7) yes C14 . C10 . C40 . 118.7(8) yes C31 . C10 . C40 . 123.4(7) yes C13 . N12 . C34 . 123.8(7) yes C13 . N12 . C38 . 109.0(7) yes C34 . N12 . C38 . 127.1(7) yes N12 . C13 . C7 . 107.5(7) yes N12 . C13 . C24 . 122.0(7) yes C7 . C13 . C24 . 130.4(8) yes C10 . C14 . C41 . 120.6(8) yes C10 . C14 . H141 . 119.9 no C41 . C14 . H141 . 119.5 no C42 2_656 C18 . C26 . 120.9(8) yes C42 2_656 C18 . H181 . 119.9 no C26 . C18 . H181 . 119.1 no H191 . O19 . H192 . 102.4 no C7 . N20 . C31 . 123.5(7) yes C7 . N20 . C38 . 110.0(6) yes C31 . N20 . C38 . 126.5(8) yes C1 2_656 C21 . C32 . 121.1(8) yes C1 2_656 C21 . H211 . 119.7 no C32 . C21 . H211 . 119.1 no N27 . C22 . C42 . 112.1(7) yes N27 . C22 . H221 . 109.0 no C42 . C22 . H221 . 109.3 no N27 . C22 . H222 . 108.8 no C42 . C22 . H222 . 108.2 no H221 . C22 . H222 . 109.5 no N27 . C23 . C36 . 121.0(8) yes N27 . C23 . C39 . 106.5(8) yes C36 . C23 . C39 . 132.3(8) yes C13 . C24 . H241 . 109.1 no C13 . C24 . H242 . 109.4 no H241 . C24 . H242 . 109.2 no C13 . C24 . H243 . 109.5 no H241 . C24 . H243 . 109.5 no H242 . C24 . H243 . 110.1 no O11 . N25 . O16 . 119.9(11) yes O11 . N25 . O33 . 116.3(11) yes O16 . N25 . O33 . 123.6(10) yes C18 . C26 . C37 . 123.2(7) yes C18 . C26 . C1 . 119.1(7) yes C37 . C26 . C1 . 117.6(7) yes C22 . N27 . C23 . 124.7(7) yes C22 . N27 . C35 . 126.1(7) yes C23 . N27 . C35 . 109.2(7) yes C40 2_555 C29 . C30 . 119.0(8) yes C40 2_555 C29 . C34 . 122.9(7) yes C30 . C29 . C34 . 118.1(7) yes C41 2_555 C30 . C29 . 119.4(8) yes C41 2_555 C30 . H301 . 120.3 no C29 . C30 . H301 . 120.3 no C10 . C31 . N20 . 114.8(7) yes C10 . C31 . H311 . 108.7 no N20 . C31 . H311 . 108.0 no C10 . C31 . H312 . 108.3 no N20 . C31 . H312 . 108.0 no H311 . C31 . H312 . 108.8 no C21 . C32 . C42 . 119.7(8) yes C21 . C32 . H321 . 119.9 no C42 . C32 . H321 . 120.5 no C29 . C34 . N12 . 112.1(6) yes C29 . C34 . H341 . 109.0 no N12 . C34 . H341 . 108.8 no C29 . C34 . H342 . 108.9 no N12 . C34 . H342 . 108.2 no H341 . C34 . H342 . 109.9 no Br2 . C35 . N5 . 125.7(6) yes Br2 . C35 . N27 . 126.6(6) yes N5 . C35 . N27 . 107.7(7) yes C23 . C36 . H362 . 108.5 no C23 . C36 . H361 . 109.7 no H362 . C36 . H361 . 109.9 no C23 . C36 . H363 . 109.4 no H362 . C36 . H363 . 109.8 no H361 . C36 . H363 . 109.5 no C26 . C37 . N5 . 113.9(7) yes C26 . C37 . H371 . 109.0 no N5 . C37 . H371 . 108.5 no C26 . C37 . H372 . 109.0 no N5 . C37 . H372 . 107.5 no H371 . C37 . H372 . 108.9 no Br1 . C38 . N20 . 125.2(6) yes Br1 . C38 . N12 . 126.9(6) yes N20 . C38 . N12 . 107.9(7) yes N5 . C39 . C23 . 107.5(8) yes N5 . C39 . C43 . 122.0(9) yes C23 . C39 . C43 . 130.5(9) yes C10 . C40 . C29 2_555 121.9(7) yes C10 . C40 . H401 . 119.6 no C29 2_555 C40 . H401 . 118.5 no C30 2_555 C41 . C14 . 120.4(8) yes C30 2_555 C41 . H411 . 119.4 no C14 . C41 . H411 . 120.1 no C22 . C42 . C32 . 118.9(7) yes C22 . C42 . C18 2_656 121.5(8) yes C32 . C42 . C18 2_656 119.6(8) yes C39 . C43 . H432 . 109.7 no C39 . C43 . H431 . 109.5 no H432 . C43 . H431 . 109.3 no C39 . C43 . H433 . 109.4 no H432 . C43 . H433 . 109.6 no H431 . C43 . H433 . 109.4 no C26 . C1 . C21 2_656 119.5(8) yes C26 . C1 . H11 . 120.2 no C21 2_656 C1 . H11 . 120.2 no loop_ _geom_hbond_atom_site_label_D _geom_hbond_site_symmetry_D _geom_hbond_atom_site_label_H _geom_hbond_site_symmetry_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_angle_DHA _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_publ_flag C22 . H221 . O19 2_656 126 0.97 2.34 3.015(13) yes C22 . H222 . O33 2_656 164 0.97 2.43 3.375(13) yes C30 . H301 . O9 1_655 152 0.94 2.59 3.453(13) yes C31 . H312 . O9 2_445 131 0.98 2.46 3.182(13) yes C34 . H341 . O17 1_655 165 0.98 2.46 3.411(13) yes C34 . H342 . O3 1_545 162 0.98 2.43 3.379(13) yes C37 . H371 . O19 1_545 120 0.97 2.43 3.043(13) yes C37 . H372 . O9 1_655 157 0.98 2.50 3.419(13) yes O3 . H31 . O11 1_455 144 0.84 2.20 2.917(13) yes O3 . H32 . O15 1_565 169 0.84 1.96 2.782(13) yes O19 . H191 . O11 . 173 0.83 1.77 2.587(13) yes O19 . H192 . O15 1_665 152 0.97 1.96 2.847(13) yes _database_code_depnum_ccdc_archive 'CCDC 963239'