# 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_120K _database_code_depnum_ccdc_archive 'CCDC 924404' #TrackingRef '17736_web_deposit_cif_file_0_HazelA.Sparkes_1360832480.4-bromocinnamic acid_combined.cif' _iucr_refine_instructions_details ; TITL testm1 in P2(1)/n CELL 0.71073 6.8994 3.8566 31.2021 90.000 90.571 90.000 ZERR 4.0000 0.0004 0.0002 0.0019 0.000 0.001 0.000 LATT 1 SYMM 0.5-X, 0.5+Y, 0.5-Z SFAC C H O BR UNIT 36 28 8 4 MERG 2 SHEL 9999.00 0.80 FMAP 2 GRID PLAN 20 TEMP -100 BOND $H EQIV $1 3-X, -Y, -Z HTAB O2 O1_$1 MPLA 6 C1 C2 C3 C4 C5 C6 MPLA 3 O1 C9 O2 CONF L.S. 20 ACTA 52 WGHT 0.044900 1.031200 FVAR 0.45437 BR1 4 0.389746 0.523760 0.211457 11.00000 0.01490 0.01839 = 0.02754 -0.00125 0.00587 0.00113 O1 3 1.407236 -0.060385 0.049721 11.00000 0.01966 0.03327 = 0.02325 0.00383 0.00311 0.00728 O2 3 1.283013 0.231012 -0.006267 11.00000 0.02106 0.04074 = 0.02215 0.00599 0.00663 0.00890 AFIX 83 H2 2 1.386504 0.163227 -0.017482 11.00000 -1.20000 AFIX 0 C1 1 0.745197 0.387552 0.106836 11.00000 0.01885 0.02096 = 0.01814 0.00175 0.00072 0.00076 AFIX 43 H1 2 0.739632 0.440060 0.077103 11.00000 -1.20000 AFIX 0 C2 1 0.589153 0.471314 0.132590 11.00000 0.01405 0.02177 = 0.02511 -0.00034 -0.00174 0.00337 AFIX 43 H2A 2 0.476927 0.578480 0.120688 11.00000 -1.20000 AFIX 0 C3 1 0.599908 0.396170 0.175790 11.00000 0.01418 0.01241 = 0.02403 -0.00190 0.00487 0.00012 C4 1 0.760420 0.234470 0.193910 11.00000 0.01917 0.01686 = 0.01865 0.00019 -0.00014 -0.00214 AFIX 43 H4 2 0.764670 0.182700 0.223671 11.00000 -1.20000 AFIX 0 C5 1 0.914688 0.149773 0.167723 11.00000 0.01239 0.01562 = 0.02458 0.00090 -0.00162 0.00042 AFIX 43 H5 2 1.025008 0.037334 0.179750 11.00000 -1.20000 AFIX 0 C6 1 0.910661 0.226960 0.123954 11.00000 0.01049 0.01651 = 0.02040 -0.00191 0.00307 -0.00170 C7 1 1.077760 0.137706 0.097618 11.00000 0.01427 0.01582 = 0.02488 -0.00203 0.00062 0.00184 AFIX 43 H7 2 1.178157 0.007083 0.111013 11.00000 -1.20000 AFIX 0 C8 1 1.102440 0.222441 0.056570 11.00000 0.01394 0.02196 = 0.02429 0.00048 0.00225 0.00369 AFIX 43 H8 2 1.004031 0.351998 0.042314 11.00000 -1.20000 AFIX 0 C9 1 1.275898 0.123106 0.032585 11.00000 0.01544 0.02156 = 0.02204 -0.00218 0.00294 0.00070 HKLF 4 REM testm1 in P2(1)/n REM R1 = 0.0345 for 1538 Fo > 4sig(Fo) and 0.0379 for all 1689 data REM 109 parameters refined using 0 restraints END WGHT 0.0453 1.0150 REM Highest difference peak 1.095, deepest hole -0.818, 1-sigma level 0.128 Q1 1 0.3923 0.5032 0.1849 11.00000 0.05 1.09 Q2 1 0.3998 0.5304 0.2417 11.00000 0.05 1.00 Q3 1 0.5876 0.4721 0.1515 11.00000 0.05 0.44 Q4 1 1.3972 -0.0783 0.0708 11.00000 0.05 0.41 Q5 1 0.9260 0.2567 0.1467 11.00000 0.05 0.38 Q6 1 0.9174 0.0250 0.2558 11.00000 0.05 0.38 Q7 1 1.2130 0.1916 0.0548 11.00000 0.05 0.36 Q8 1 1.4208 0.0721 0.0334 11.00000 0.05 0.35 Q9 1 0.8845 0.1443 0.1384 11.00000 0.05 0.35 Q10 1 1.3221 -0.0196 0.0330 11.00000 0.05 0.35 Q11 1 1.0790 0.0969 0.0704 11.00000 0.05 0.35 Q12 1 0.4663 0.1444 0.2503 11.00000 0.05 0.35 Q13 1 0.7236 0.0170 0.1321 11.00000 0.05 0.34 Q14 1 1.4980 -0.0536 0.0383 11.00000 0.05 0.33 Q15 1 0.6819 0.4569 0.1281 11.00000 0.05 0.33 Q16 1 1.0213 0.3213 0.2387 11.00000 0.05 0.33 Q17 1 1.0942 0.2769 0.0792 11.00000 0.05 0.33 Q18 1 0.9914 0.2202 0.1176 11.00000 0.05 0.30 Q19 1 0.3449 0.5528 0.1553 11.00000 0.05 0.29 Q20 1 0.2509 0.5365 0.2005 11.00000 0.05 0.29 ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C9 H7 Br O2' _chemical_formula_sum 'C9 H7 Br O2' _chemical_formula_weight 227.06 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' 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 monoclinic _symmetry_space_group_name_H-M 'P 21/n' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 6.8994(4) _cell_length_b 3.8566(2) _cell_length_c 31.2021(19) _cell_angle_alpha 90.00 _cell_angle_beta 90.5710(10) _cell_angle_gamma 90.00 _cell_volume 830.19(8) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 3210 _cell_measurement_theta_min 5.222 _cell_measurement_theta_max 56.560 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.817 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 448 _exptl_absorpt_coefficient_mu 4.901 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.641 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_process_details 'SADABS (G. Sheldrick, 1998)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 120(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 'Bruker SMART 6K CCD Detector' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 8 _diffrn_reflns_number 4802 _diffrn_reflns_av_R_equivalents 0.0377 _diffrn_reflns_av_sigmaI/netI 0.0441 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -4 _diffrn_reflns_limit_k_max 4 _diffrn_reflns_limit_l_min -39 _diffrn_reflns_limit_l_max 37 _diffrn_reflns_theta_min 1.31 _diffrn_reflns_theta_max 26.35 _reflns_number_total 1689 _reflns_number_gt 1538 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'SMART version 5.054 (Bruker, 1999)' _computing_cell_refinement 'SAINT version 6.45A (Bruker, 2003)' _computing_data_reduction 'SAINT version 6.45A (Bruker, 2003)' _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'ORTEP3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.0449P)^2^+1.0312P] 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 1689 _refine_ls_number_parameters 109 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0379 _refine_ls_R_factor_gt 0.0345 _refine_ls_wR_factor_ref 0.0921 _refine_ls_wR_factor_gt 0.0900 _refine_ls_goodness_of_fit_ref 1.106 _refine_ls_restrained_S_all 1.106 _refine_ls_shift/su_max 0.000 _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 0.38975(4) 0.52376(7) 0.211457(10) 0.02024(15) Uani 1 1 d . . . O1 O 1.4072(4) -0.0604(6) 0.04972(8) 0.0254(5) Uani 1 1 d . . . O2 O 1.2830(3) 0.2310(7) -0.00627(7) 0.0279(5) Uani 1 1 d . . . H2 H 1.3865 0.1632 -0.0175 0.034 Uiso 1 1 calc R . . C1 C 0.7452(5) 0.3876(8) 0.10684(10) 0.0193(6) Uani 1 1 d . . . H1 H 0.7396 0.4401 0.0771 0.023 Uiso 1 1 calc R . . C2 C 0.5892(5) 0.4713(8) 0.13259(11) 0.0203(7) Uani 1 1 d . . . H2A H 0.4769 0.5785 0.1207 0.024 Uiso 1 1 calc R . . C3 C 0.5999(4) 0.3962(8) 0.17579(10) 0.0168(6) Uani 1 1 d . . . C4 C 0.7604(4) 0.2345(8) 0.19391(10) 0.0182(6) Uani 1 1 d . . . H4 H 0.7647 0.1827 0.2237 0.022 Uiso 1 1 calc R . . C5 C 0.9147(4) 0.1498(8) 0.16772(10) 0.0175(6) Uani 1 1 d . . . H5 H 1.0250 0.0373 0.1798 0.021 Uiso 1 1 calc R . . C6 C 0.9107(4) 0.2270(7) 0.12395(10) 0.0158(6) Uani 1 1 d . . . C7 C 1.0778(4) 0.1377(8) 0.09762(10) 0.0183(6) Uani 1 1 d . . . H7 H 1.1782 0.0071 0.1110 0.022 Uiso 1 1 calc R . . C8 C 1.1024(5) 0.2224(8) 0.05657(10) 0.0200(6) Uani 1 1 d . . . H8 H 1.0040 0.3520 0.0423 0.024 Uiso 1 1 calc R . . C9 C 1.2759(5) 0.1231(8) 0.03259(10) 0.0197(6) 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 0.0149(2) 0.0184(2) 0.0275(2) -0.00125(11) 0.00587(14) 0.00113(10) O1 0.0197(13) 0.0333(12) 0.0233(12) 0.0038(10) 0.0031(9) 0.0073(10) O2 0.0211(13) 0.0407(14) 0.0222(12) 0.0060(10) 0.0066(9) 0.0089(10) C1 0.0189(16) 0.0210(15) 0.0181(15) 0.0017(12) 0.0007(12) 0.0008(12) C2 0.0141(16) 0.0218(16) 0.0251(17) -0.0003(12) -0.0017(13) 0.0034(11) C3 0.0142(15) 0.0124(13) 0.0240(16) -0.0019(12) 0.0049(12) 0.0001(11) C4 0.0192(17) 0.0169(14) 0.0187(15) 0.0002(11) -0.0001(12) -0.0021(12) C5 0.0124(15) 0.0156(14) 0.0246(16) 0.0009(12) -0.0016(12) 0.0004(11) C6 0.0105(15) 0.0165(13) 0.0204(15) -0.0019(11) 0.0031(11) -0.0017(11) C7 0.0143(15) 0.0158(14) 0.0249(16) -0.0020(12) 0.0006(12) 0.0018(11) C8 0.0139(16) 0.0220(15) 0.0243(16) 0.0005(12) 0.0022(12) 0.0037(12) C9 0.0154(16) 0.0216(15) 0.0220(16) -0.0022(13) 0.0029(12) 0.0007(12) _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 C3 1.901(3) . ? O1 C9 1.264(4) . ? O2 C9 1.283(4) . ? O2 H2 0.8400 . ? C1 C2 1.388(5) . ? C1 C6 1.400(4) . ? C1 H1 0.9500 . ? C2 C3 1.380(5) . ? C2 H2A 0.9500 . ? C3 C4 1.387(4) . ? C4 C5 1.387(4) . ? C4 H4 0.9500 . ? C5 C6 1.398(4) . ? C5 H5 0.9500 . ? C6 C7 1.463(4) . ? C7 C8 1.334(4) . ? C7 H7 0.9500 . ? C8 C9 1.469(4) . ? C8 H8 0.9500 . ? 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 C9 O2 H2 109.5 . . ? C2 C1 C6 121.1(3) . . ? C2 C1 H1 119.5 . . ? C6 C1 H1 119.5 . . ? C3 C2 C1 118.8(3) . . ? C3 C2 H2A 120.6 . . ? C1 C2 H2A 120.6 . . ? C2 C3 C4 121.8(3) . . ? C2 C3 Br1 118.9(2) . . ? C4 C3 Br1 119.2(2) . . ? C3 C4 C5 118.7(3) . . ? C3 C4 H4 120.7 . . ? C5 C4 H4 120.7 . . ? C4 C5 C6 121.2(3) . . ? C4 C5 H5 119.4 . . ? C6 C5 H5 119.4 . . ? C5 C6 C1 118.4(3) . . ? C5 C6 C7 119.4(3) . . ? C1 C6 C7 122.3(3) . . ? C8 C7 C6 126.2(3) . . ? C8 C7 H7 116.9 . . ? C6 C7 H7 116.9 . . ? C7 C8 C9 122.5(3) . . ? C7 C8 H8 118.7 . . ? C9 C8 H8 118.7 . . ? O1 C9 O2 123.2(3) . . ? O1 C9 C8 121.0(3) . . ? O2 C9 C8 115.8(3) . . ? 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 C6 C1 C2 C3 0.5(5) . . . . ? C1 C2 C3 C4 -1.1(5) . . . . ? C1 C2 C3 Br1 178.1(2) . . . . ? C2 C3 C4 C5 0.6(5) . . . . ? Br1 C3 C4 C5 -178.5(2) . . . . ? C3 C4 C5 C6 0.5(4) . . . . ? C4 C5 C6 C1 -1.0(4) . . . . ? C4 C5 C6 C7 179.1(3) . . . . ? C2 C1 C6 C5 0.5(5) . . . . ? C2 C1 C6 C7 -179.6(3) . . . . ? C5 C6 C7 C8 -173.5(3) . . . . ? C1 C6 C7 C8 6.6(5) . . . . ? C6 C7 C8 C9 179.7(3) . . . . ? C7 C8 C9 O1 2.7(5) . . . . ? C7 C8 C9 O2 -178.0(3) . . . . ? 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 O2 H2 O1 0.84 1.80 2.626(3) 169.7 3_855 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.095 _refine_diff_density_min -0.818 _refine_diff_density_rms 0.128 data_240K _database_code_depnum_ccdc_archive 'CCDC 924405' #TrackingRef '17736_web_deposit_cif_file_0_HazelA.Sparkes_1360832480.4-bromocinnamic acid_combined.cif' _iucr_refine_instructions_details ; TITL testa in P2(1)/n CELL 0.71073 6.8823 3.9043 31.4618 90.000 90.077 90.000 ZERR 4.0000 0.0002 0.0001 0.0012 0.000 0.003 0.000 LATT 1 SYMM 0.5-X, 0.5+Y, 0.5-Z SFAC C H O BR UNIT 36 28 8 4 MERG 2 SHEL 99999.00 0.78 FMAP 2 GRID PLAN 20 TEMP -100 BOND $H EQIV $1 3-X, -Y, -Z HTAB O2 O1_$1 EQIV $2 2-X, 1-Y, -Z HTAB C1 O2_$2 CONF MPLA 6 C1 C2 C3 C4 C5 C6 MPLA 3 O1 C9 O2 OMIT -8 1 2 L.S. 20 ACTA 52 WGHT 0.023400 0.958400 FVAR 4.70561 BR1 4 0.391912 0.558505 0.211242 11.00000 0.03020 0.03693 = 0.04326 -0.00270 0.01339 0.00197 O1 3 1.407093 -0.044914 0.050005 11.00000 0.03580 0.06266 = 0.03434 0.00811 0.00571 0.01776 O2 3 1.283332 0.226833 -0.006086 11.00000 0.04242 0.07887 = 0.03058 0.01160 0.01175 0.02502 AFIX 83 H2 2 1.387289 0.157943 -0.017128 11.00000 -1.20000 AFIX 0 C1 1 0.747471 0.409016 0.107142 11.00000 0.03277 0.03940 = 0.02598 0.00469 0.00011 0.00527 AFIX 43 H1 2 0.741470 0.455145 0.077521 11.00000 -1.20000 AFIX 0 C2 1 0.592121 0.499291 0.132780 11.00000 0.02613 0.03395 = 0.03584 0.00346 -0.00160 0.00520 AFIX 43 H2A 2 0.481024 0.608696 0.121050 11.00000 -1.20000 AFIX 0 C3 1 0.601843 0.427314 0.175640 11.00000 0.02499 0.02587 = 0.03061 -0.00291 0.00697 -0.00195 C4 1 0.761735 0.269983 0.193362 11.00000 0.03306 0.03167 = 0.02356 0.00177 0.00230 0.00004 AFIX 43 H4 2 0.766070 0.221831 0.222947 11.00000 -1.20000 AFIX 0 C5 1 0.916086 0.183225 0.167283 11.00000 0.02254 0.03401 = 0.03102 0.00306 -0.00186 0.00365 AFIX 43 H5 2 1.026904 0.074500 0.179235 11.00000 -1.20000 AFIX 0 C6 1 0.911833 0.252362 0.123909 11.00000 0.02382 0.02371 = 0.02881 -0.00021 0.00245 -0.00040 C7 1 1.078958 0.158966 0.097405 11.00000 0.02579 0.03281 = 0.03137 -0.00005 0.00228 0.00363 AFIX 43 H7 2 1.179963 0.033100 0.110836 11.00000 -1.20000 AFIX 0 C8 1 1.103165 0.232196 0.056761 11.00000 0.02712 0.04104 = 0.03492 0.00230 0.00401 0.00851 AFIX 43 H8 2 1.004344 0.357355 0.042476 11.00000 -1.20000 AFIX 0 C9 1 1.275966 0.128707 0.032718 11.00000 0.03200 0.03932 = 0.02730 0.00067 0.00453 0.00132 HKLF 4 REM testa in P2(1)/n REM R1 = 0.0319 for 1575 Fo > 4sig(Fo) and 0.0413 for all 1847 data REM 109 parameters refined using 0 restraints END WGHT 0.0234 0.9584 REM Highest difference peak 0.446, deepest hole -0.964, 1-sigma level 0.067 Q1 1 0.4033 0.5766 0.1807 11.00000 0.05 0.45 Q2 1 0.3943 0.7587 0.2133 11.00000 0.05 0.44 Q3 1 0.3368 0.4562 0.1916 11.00000 0.05 0.40 Q4 1 1.5027 -0.0875 0.0377 11.00000 0.05 0.34 Q5 1 0.3665 0.5633 0.2494 11.00000 0.05 0.34 Q6 1 0.4714 0.4173 0.2243 11.00000 0.05 0.31 Q7 1 0.2426 0.5980 0.2120 11.00000 0.05 0.29 Q8 1 0.8825 0.4567 0.1210 11.00000 0.05 0.27 Q9 1 1.3379 -0.0948 0.0367 11.00000 0.05 0.27 Q10 1 1.2146 0.2374 0.0532 11.00000 0.05 0.26 Q11 1 1.1020 0.3285 0.0840 11.00000 0.05 0.25 Q12 1 0.6983 0.4002 0.1821 11.00000 0.05 0.24 Q13 1 0.9191 0.2505 0.1445 11.00000 0.05 0.23 Q14 1 0.5350 0.6107 0.2132 11.00000 0.05 0.22 Q15 1 1.4035 0.1299 0.0433 11.00000 0.05 0.21 Q16 1 0.3226 0.3059 0.2257 11.00000 0.05 0.21 Q17 1 1.0060 0.2382 0.1122 11.00000 0.05 0.21 Q18 1 0.5137 0.6832 0.2362 11.00000 0.05 0.21 Q19 1 0.7218 0.6157 0.1187 11.00000 0.05 0.20 Q20 1 0.3217 0.2280 0.2087 11.00000 0.05 0.20 ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C9 H7 Br O2' _chemical_formula_sum 'C9 H7 Br O2' _chemical_formula_weight 227.06 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' 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 monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 6.8823(2) _cell_length_b 3.90430(10) _cell_length_c 31.4618(12) _cell_angle_alpha 90.00 _cell_angle_beta 90.077(3) _cell_angle_gamma 90.00 _cell_volume 845.40(5) _cell_formula_units_Z 4 _cell_measurement_temperature 240(2) _cell_measurement_reflns_used 5802 _cell_measurement_theta_min 2.5845 _cell_measurement_theta_max 30.8001 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.784 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 448 _exptl_absorpt_coefficient_mu 4.813 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.44029 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET) (compiled May 6 2009,17:20:42) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 240(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Sapphire3, Gemini ultra' _diffrn_measurement_method ? _diffrn_detector_area_resol_mean 16.1511 _diffrn_reflns_number 10137 _diffrn_reflns_av_R_equivalents 0.0301 _diffrn_reflns_av_sigmaI/netI 0.0231 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_k_max 4 _diffrn_reflns_limit_l_min -40 _diffrn_reflns_limit_l_max 40 _diffrn_reflns_theta_min 2.59 _diffrn_reflns_theta_max 27.10 _reflns_number_total 1847 _reflns_number_gt 1575 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET) (compiled May 6 2009,17:20:42) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET) (compiled May 6 2009,17:20:42) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET) (compiled May 6 2009,17:20:42) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'ORTEP3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.0234P)^2^+0.9584P] 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 1847 _refine_ls_number_parameters 109 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0413 _refine_ls_R_factor_gt 0.0319 _refine_ls_wR_factor_ref 0.0651 _refine_ls_wR_factor_gt 0.0634 _refine_ls_goodness_of_fit_ref 1.118 _refine_ls_restrained_S_all 1.118 _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 0.39191(4) 0.55851(8) 0.211242(10) 0.03679(11) Uani 1 1 d . . . O1 O 1.4071(3) -0.0449(6) 0.05001(7) 0.0443(6) Uani 1 1 d . . . O2 O 1.2833(3) 0.2268(7) -0.00609(6) 0.0506(6) Uani 1 1 d . . . H2 H 1.3873 0.1579 -0.0171 0.061 Uiso 1 1 calc R . . C1 C 0.7475(4) 0.4090(8) 0.10714(9) 0.0327(6) Uani 1 1 d . . . H1 H 0.7415 0.4551 0.0775 0.039 Uiso 1 1 calc R . . C2 C 0.5921(4) 0.4993(7) 0.13278(9) 0.0320(6) Uani 1 1 d . . . H2A H 0.4810 0.6087 0.1211 0.038 Uiso 1 1 calc R . . C3 C 0.6018(4) 0.4273(7) 0.17564(8) 0.0272(6) Uani 1 1 d . . . C4 C 0.7617(4) 0.2700(7) 0.19336(8) 0.0294(6) Uani 1 1 d . . . H4 H 0.7661 0.2218 0.2229 0.035 Uiso 1 1 calc R . . C5 C 0.9161(4) 0.1832(8) 0.16728(9) 0.0292(6) Uani 1 1 d . . . H5 H 1.0269 0.0745 0.1792 0.035 Uiso 1 1 calc R . . C6 C 0.9118(4) 0.2524(7) 0.12391(8) 0.0254(6) Uani 1 1 d . . . C7 C 1.0790(4) 0.1590(7) 0.09740(9) 0.0300(6) Uani 1 1 d . . . H7 H 1.1800 0.0331 0.1108 0.036 Uiso 1 1 calc R . . C8 C 1.1032(4) 0.2322(8) 0.05676(9) 0.0344(7) Uani 1 1 d . . . H8 H 1.0043 0.3574 0.0425 0.041 Uiso 1 1 calc R . . C9 C 1.2760(4) 0.1287(8) 0.03272(9) 0.0329(7) 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 0.03020(16) 0.03693(16) 0.04326(18) -0.00270(14) 0.01339(12) 0.00197(14) O1 0.0358(12) 0.0627(15) 0.0343(11) 0.0081(11) 0.0057(9) 0.0178(11) O2 0.0424(13) 0.0789(18) 0.0306(12) 0.0116(11) 0.0118(10) 0.0250(12) C1 0.0328(16) 0.0394(17) 0.0260(14) 0.0047(12) 0.0001(11) 0.0053(13) C2 0.0261(14) 0.0339(17) 0.0358(15) 0.0035(12) -0.0016(11) 0.0052(11) C3 0.0250(13) 0.0259(13) 0.0306(14) -0.0029(12) 0.0070(11) -0.0019(12) C4 0.0331(16) 0.0317(16) 0.0236(14) 0.0018(11) 0.0023(11) 0.0000(12) C5 0.0225(14) 0.0340(14) 0.0310(15) 0.0031(12) -0.0019(11) 0.0037(11) C6 0.0238(14) 0.0237(15) 0.0288(14) -0.0002(11) 0.0024(11) -0.0004(10) C7 0.0258(15) 0.0328(15) 0.0314(15) 0.0000(11) 0.0023(11) 0.0036(11) C8 0.0271(15) 0.0410(18) 0.0349(16) 0.0023(13) 0.0040(12) 0.0085(13) C9 0.0320(16) 0.0393(18) 0.0273(15) 0.0007(12) 0.0045(12) 0.0013(13) _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 C3 1.900(3) . ? O1 C9 1.252(4) . ? O2 C9 1.281(3) . ? O2 H2 0.8400 . ? C1 C2 1.386(4) . ? C1 C6 1.389(4) . ? C1 H1 0.9500 . ? C2 C3 1.379(4) . ? C2 H2A 0.9500 . ? C3 C4 1.377(4) . ? C4 C5 1.385(4) . ? C4 H4 0.9500 . ? C5 C6 1.391(4) . ? C5 H5 0.9500 . ? C6 C7 1.468(4) . ? C7 C8 1.321(4) . ? C7 H7 0.9500 . ? C8 C9 1.467(4) . ? C8 H8 0.9500 . ? 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 C9 O2 H2 109.5 . . ? C2 C1 C6 121.3(3) . . ? C2 C1 H1 119.4 . . ? C6 C1 H1 119.4 . . ? C3 C2 C1 118.7(3) . . ? C3 C2 H2A 120.6 . . ? C1 C2 H2A 120.6 . . ? C4 C3 C2 121.6(2) . . ? C4 C3 Br1 119.3(2) . . ? C2 C3 Br1 119.1(2) . . ? C3 C4 C5 118.8(2) . . ? C3 C4 H4 120.6 . . ? C5 C4 H4 120.6 . . ? C4 C5 C6 121.2(3) . . ? C4 C5 H5 119.4 . . ? C6 C5 H5 119.4 . . ? C1 C6 C5 118.3(2) . . ? C1 C6 C7 122.1(2) . . ? C5 C6 C7 119.6(3) . . ? C8 C7 C6 126.6(3) . . ? C8 C7 H7 116.7 . . ? C6 C7 H7 116.7 . . ? C7 C8 C9 122.9(3) . . ? C7 C8 H8 118.6 . . ? C9 C8 H8 118.6 . . ? O1 C9 O2 123.1(3) . . ? O1 C9 C8 120.6(3) . . ? O2 C9 C8 116.3(3) . . ? 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 C6 C1 C2 C3 -0.7(4) . . . . ? C1 C2 C3 C4 0.2(4) . . . . ? C1 C2 C3 Br1 178.7(2) . . . . ? C2 C3 C4 C5 0.1(4) . . . . ? Br1 C3 C4 C5 -178.4(2) . . . . ? C3 C4 C5 C6 0.0(4) . . . . ? C2 C1 C6 C5 0.9(4) . . . . ? C2 C1 C6 C7 -179.2(3) . . . . ? C4 C5 C6 C1 -0.5(4) . . . . ? C4 C5 C6 C7 179.5(3) . . . . ? C1 C6 C7 C8 5.9(5) . . . . ? C5 C6 C7 C8 -174.1(3) . . . . ? C6 C7 C8 C9 179.8(3) . . . . ? C7 C8 C9 O1 2.0(5) . . . . ? C7 C8 C9 O2 -177.7(3) . . . . ? 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 O2 H2 O1 0.84 1.81 2.638(3) 169.2 3_855 C1 H1 O2 0.95 2.57 3.489(3) 162.0 3_765 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 0.446 _refine_diff_density_min -0.964 _refine_diff_density_rms 0.067 data_300K _database_code_depnum_ccdc_archive 'CCDC 924406' #TrackingRef '17736_web_deposit_cif_file_0_HazelA.Sparkes_1360832480.4-bromocinnamic acid_combined.cif' _iucr_refine_instructions_details ; TITL testa in P2(1)/n CELL 0.71073 6.6422 3.9472 32.8997 90.000 95.552 90.000 ZERR 4.0000 0.0004 0.0004 0.0027 0.000 0.007 0.000 LATT 1 SYMM 0.5-X, 0.5+Y, 0.5-Z SFAC C H O BR UNIT 36 28 8 4 MERG 2 SHEL 99999.00 0.82 FMAP 2 GRID PLAN 20 TEMP -100 MPLA 6 C1 C2 C3 C4 C5 C6 MPLA 3 O1 C9 O2 DFIX 0.86 0.01 O1 H1A O2 H2A BOND $H CONF EQIV $1 -X-1, -Y, -Z HTAB O1 O2_$1 HTAB O2 O1_$1 L.S. 20 ACTA 52 WGHT 0.042400 0.104200 FVAR 4.88001 BR1 4 0.590116 0.988046 0.213012 11.00000 0.04559 0.04985 = 0.05336 -0.00603 -0.00665 -0.00241 O1 3 -0.423856 0.099480 0.050005 11.00000 0.05197 0.09627 = 0.04852 -0.00781 0.00637 -0.02731 AFIX 83 H1A 2 -0.513346 0.023545 0.032588 10.50000 -1.20000 AFIX 0 O2 3 -0.265878 0.166181 -0.005656 11.00000 0.06053 0.13719 = 0.03881 -0.00814 0.00518 -0.04573 AFIX 83 H2A 2 -0.374744 0.082282 -0.016269 10.50000 -1.20000 AFIX 0 C1 1 0.258623 0.622689 0.110174 11.00000 0.04606 0.05644 = 0.03388 -0.00055 0.00994 -0.00558 AFIX 43 H1 2 0.279593 0.593977 0.082226 11.00000 -1.20000 AFIX 0 C2 1 0.409680 0.760885 0.136323 11.00000 0.03435 0.05899 = 0.04418 -0.00092 0.00944 -0.00859 AFIX 43 H2 2 0.533754 0.827926 0.126602 11.00000 -1.20000 AFIX 0 C3 1 0.379540 0.801418 0.176835 11.00000 0.03603 0.03393 = 0.03551 -0.00007 -0.00187 0.00117 C4 1 0.200576 0.708972 0.191232 11.00000 0.04503 0.05948 = 0.03781 -0.00410 0.00722 -0.00288 AFIX 43 H4 2 0.180794 0.740416 0.219196 11.00000 -1.20000 AFIX 0 C5 1 0.050056 0.570253 0.164746 11.00000 0.03905 0.04980 = 0.04654 -0.00131 0.01215 -0.00988 AFIX 43 H5 2 -0.073640 0.505104 0.174775 11.00000 -1.20000 AFIX 0 C6 1 0.074529 0.523029 0.123637 11.00000 0.03881 0.03798 = 0.03972 -0.00392 0.00543 -0.00283 C7 1 -0.090868 0.377770 0.096505 11.00000 0.03388 0.03905 = 0.04840 0.00103 0.00491 -0.00624 AFIX 43 H7 2 -0.206248 0.305607 0.109127 11.00000 -1.20000 AFIX 0 C8 1 -0.098724 0.335455 0.056911 11.00000 0.04153 0.06413 = 0.04314 0.00226 -0.00010 -0.01644 AFIX 43 H8 2 0.015410 0.400713 0.043439 11.00000 -1.20000 AFIX 0 C9 1 -0.272916 0.193784 0.032395 11.00000 0.04148 0.05800 = 0.04046 0.00288 0.00212 -0.00482 HKLF 4 REM testa in P2(1)/n REM R1 = 0.0389 for 1114 Fo > 4sig(Fo) and 0.0661 for all 1625 data REM 109 parameters refined using 2 restraints END WGHT 0.0426 0.0951 REM Highest difference peak 0.409, deepest hole -0.441, 1-sigma level 0.069 Q1 1 0.5913 1.0234 0.1805 11.00000 0.05 0.41 Q2 1 0.6094 1.2011 0.1890 11.00000 0.05 0.35 Q3 1 0.6349 0.8810 0.1859 11.00000 0.05 0.33 Q4 1 0.5665 0.8511 0.2416 11.00000 0.05 0.33 Q5 1 0.5501 1.0969 0.2516 11.00000 0.05 0.30 Q6 1 0.4831 0.9361 0.1884 11.00000 0.05 0.26 Q7 1 0.5787 1.2386 0.2369 11.00000 0.05 0.24 Q8 1 0.6866 1.0027 0.2432 11.00000 0.05 0.22 Q9 1 0.2745 0.5263 0.1063 11.00000 0.05 0.21 Q10 1 0.4922 1.1892 0.2035 11.00000 0.05 0.21 Q11 1 -0.2599 0.0102 0.0067 11.00000 0.05 0.21 Q12 1 0.5661 0.9977 0.1540 11.00000 0.05 0.20 Q13 1 0.0619 0.5373 0.2236 11.00000 0.05 0.20 Q14 1 -0.4325 0.3003 0.0385 11.00000 0.05 0.19 Q15 1 0.0607 0.6537 0.1386 11.00000 0.05 0.19 Q16 1 -0.0056 0.4917 0.1678 11.00000 0.05 0.19 Q17 1 -0.2972 0.4376 0.1815 11.00000 0.05 0.18 Q18 1 0.2665 0.7456 0.0846 11.00000 0.05 0.17 Q19 1 0.0908 0.4791 0.1528 11.00000 0.05 0.17 Q20 1 0.4925 0.9624 0.1056 11.00000 0.05 0.16 ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C9 H7 Br O2' _chemical_formula_sum 'C9 H7 Br O2' _chemical_formula_weight 227.06 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' 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 monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 6.6422(4) _cell_length_b 3.9472(4) _cell_length_c 32.900(3) _cell_angle_alpha 90.00 _cell_angle_beta 95.552(7) _cell_angle_gamma 90.00 _cell_volume 858.52(12) _cell_formula_units_Z 4 _cell_measurement_temperature 300(2) _cell_measurement_reflns_used 1385 _cell_measurement_theta_min 3.0741 _cell_measurement_theta_max 32.2058 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_max 0.23 _exptl_crystal_size_mid 0.20 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.757 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 448 _exptl_absorpt_coefficient_mu 4.740 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.5490 _exptl_absorpt_correction_T_max 1.0000 _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET) (compiled May 6 2009,17:20:42) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_special_details ; ? ; _diffrn_ambient_temperature 300(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Sapphire3, Gemini ultra' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 3274 _diffrn_reflns_av_R_equivalents 0.0237 _diffrn_reflns_av_sigmaI/netI 0.0396 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -4 _diffrn_reflns_limit_k_max 3 _diffrn_reflns_limit_l_min -25 _diffrn_reflns_limit_l_max 40 _diffrn_reflns_theta_min 3.08 _diffrn_reflns_theta_max 25.68 _reflns_number_total 1625 _reflns_number_gt 1114 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET) (compiled May 6 2009,17:20:42) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET) (compiled May 6 2009,17:20:42) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.33.41 (release 06-05-2009 CrysAlis171 .NET) (compiled May 6 2009,17:20:42) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'ORTEP3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.0424P)^2^+0.1042P] 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 1625 _refine_ls_number_parameters 109 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0661 _refine_ls_R_factor_gt 0.0389 _refine_ls_wR_factor_ref 0.0868 _refine_ls_wR_factor_gt 0.0810 _refine_ls_goodness_of_fit_ref 1.041 _refine_ls_restrained_S_all 1.043 _refine_ls_shift/su_max 0.000 _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 0.59012(6) 0.98805(12) 0.213012(13) 0.05034(18) Uani 1 1 d . . . O1 O -0.4239(5) 0.0995(9) 0.05000(9) 0.0655(9) Uani 1 1 d D . . H1A H -0.5133 0.0235 0.0326 0.079 Uiso 0.50 1 calc PRD . . O2 O -0.2659(5) 0.1662(10) -0.00566(9) 0.0788(11) Uani 1 1 d D . . H2A H -0.3747 0.0823 -0.0163 0.095 Uiso 0.50 1 calc PRD . . C1 C 0.2586(6) 0.6227(11) 0.11017(12) 0.0451(11) Uani 1 1 d . . . H1 H 0.2796 0.5940 0.0822 0.054 Uiso 1 1 calc R . . C2 C 0.4097(6) 0.7609(10) 0.13632(12) 0.0455(11) Uani 1 1 d . . . H2 H 0.5338 0.8279 0.1266 0.055 Uiso 1 1 calc R . . C3 C 0.3795(6) 0.8014(10) 0.17683(11) 0.0355(9) Uani 1 1 d . . . C4 C 0.2006(6) 0.7090(11) 0.19123(12) 0.0472(11) Uani 1 1 d . . . H4 H 0.1808 0.7404 0.2192 0.057 Uiso 1 1 calc R . . C5 C 0.0501(6) 0.5703(10) 0.16475(12) 0.0446(11) Uani 1 1 d . . . H5 H -0.0736 0.5051 0.1748 0.054 Uiso 1 1 calc R . . C6 C 0.0745(6) 0.5230(9) 0.12364(12) 0.0387(9) Uani 1 1 d . . . C7 C -0.0909(6) 0.3778(10) 0.09650(13) 0.0404(10) Uani 1 1 d . . . H7 H -0.2062 0.3056 0.1091 0.048 Uiso 1 1 calc R . . C8 C -0.0987(6) 0.3355(12) 0.05691(12) 0.0499(11) Uani 1 1 d . . . H8 H 0.0154 0.4007 0.0434 0.060 Uiso 1 1 calc R . . C9 C -0.2729(7) 0.1938(11) 0.03239(13) 0.0468(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 Br1 0.0456(3) 0.0498(3) 0.0534(3) -0.0060(2) -0.00665(17) -0.0024(2) O1 0.0520(19) 0.096(3) 0.0485(19) -0.0078(17) 0.0064(15) -0.0273(18) O2 0.061(2) 0.137(3) 0.0388(19) -0.008(2) 0.0052(16) -0.046(2) C1 0.046(3) 0.056(3) 0.034(2) -0.0005(19) 0.0099(19) -0.006(2) C2 0.034(2) 0.059(3) 0.044(3) -0.001(2) 0.0094(19) -0.009(2) C3 0.036(2) 0.034(2) 0.036(2) -0.0001(17) -0.0019(17) 0.0012(18) C4 0.045(3) 0.059(3) 0.038(2) -0.004(2) 0.007(2) -0.003(2) C5 0.039(2) 0.050(3) 0.047(3) -0.0013(19) 0.0122(19) -0.0099(19) C6 0.039(2) 0.038(2) 0.040(2) -0.004(2) 0.0054(16) -0.003(2) C7 0.034(2) 0.039(2) 0.048(3) 0.0010(19) 0.0049(19) -0.0062(17) C8 0.042(3) 0.064(3) 0.043(3) 0.002(2) 0.000(2) -0.016(2) C9 0.041(2) 0.058(3) 0.040(3) 0.003(2) 0.002(2) -0.005(2) _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 C3 1.896(4) . ? O1 C9 1.262(5) . ? O1 H1A 0.8400 . ? O2 C9 1.262(5) . ? O2 H2A 0.8400 . ? C1 C2 1.370(5) . ? C1 C6 1.397(5) . ? C1 H1 0.9500 . ? C2 C3 1.376(5) . ? C2 H2 0.9500 . ? C3 C4 1.371(5) . ? C4 C5 1.375(5) . ? C4 H4 0.9500 . ? C5 C6 1.390(5) . ? C5 H5 0.9500 . ? C6 C7 1.464(5) . ? C7 C8 1.309(5) . ? C7 H7 0.9500 . ? C8 C9 1.457(5) . ? C8 H8 0.9500 . ? 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 C9 O1 H1A 109.5 . . ? C9 O2 H2A 109.5 . . ? C2 C1 C6 121.6(4) . . ? C2 C1 H1 119.2 . . ? C6 C1 H1 119.2 . . ? C1 C2 C3 119.2(4) . . ? C1 C2 H2 120.4 . . ? C3 C2 H2 120.4 . . ? C4 C3 C2 121.1(4) . . ? C4 C3 Br1 119.9(3) . . ? C2 C3 Br1 119.1(3) . . ? C3 C4 C5 119.3(4) . . ? C3 C4 H4 120.4 . . ? C5 C4 H4 120.4 . . ? C4 C5 C6 121.6(4) . . ? C4 C5 H5 119.2 . . ? C6 C5 H5 119.2 . . ? C5 C6 C1 117.3(4) . . ? C5 C6 C7 119.6(4) . . ? C1 C6 C7 123.0(4) . . ? C8 C7 C6 127.7(4) . . ? C8 C7 H7 116.1 . . ? C6 C7 H7 116.1 . . ? C7 C8 C9 123.6(4) . . ? C7 C8 H8 118.2 . . ? C9 C8 H8 118.2 . . ? O1 C9 O2 122.5(4) . . ? O1 C9 C8 118.9(4) . . ? O2 C9 C8 118.6(4) . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6 C1 C2 C3 0.2(7) . . . . ? C1 C2 C3 C4 -0.6(6) . . . . ? C1 C2 C3 Br1 179.3(3) . . . . ? C2 C3 C4 C5 0.7(6) . . . . ? Br1 C3 C4 C5 -179.2(3) . . . . ? C3 C4 C5 C6 -0.3(6) . . . . ? C4 C5 C6 C1 -0.1(6) . . . . ? C4 C5 C6 C7 -179.3(4) . . . . ? C2 C1 C6 C5 0.1(6) . . . . ? C2 C1 C6 C7 179.4(4) . . . . ? C5 C6 C7 C8 175.4(5) . . . . ? C1 C6 C7 C8 -3.8(7) . . . . ? C6 C7 C8 C9 -178.7(4) . . . . ? C7 C8 C9 O1 -1.5(7) . . . . ? C7 C8 C9 O2 179.4(5) . . . . ? 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 O1 H1A O2 0.84 1.80 2.626(4) 166.5 3_455 O2 H2A O1 0.84 1.80 2.626(4) 166.1 3_455 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 25.68 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.409 _refine_diff_density_min -0.441 _refine_diff_density_rms 0.069 data_irradiationproduct _database_code_depnum_ccdc_archive 'CCDC 924407' #TrackingRef '17736_web_deposit_cif_file_0_HazelA.Sparkes_1360832480.4-bromocinnamic acid_combined.cif' _iucr_refine_instructions_details ; TITL testa in P-1 CELL 0.71073 11.3180 11.3592 16.8666 98.753 102.761 103.029 ZERR 4.0000 0.0004 0.0004 0.0006 0.003 0.003 0.003 LATT 1 SFAC C H O BR UNIT 83.2 72 19.6 8 MERG 2 SHEL 99999.00 0.75 FMAP 2 GRID PLAN 20 TEMP -100 DFIX 1.41 0.003 O9A C37A O9A C40A O9B C37B O9B C40B DFIX 1.50 0.003 C37A C38A C39A C40A C37B C38B C39B C40B C38A C39A C38B C39B SIMU 0.01 O9A O9B C37A C38A C39A C40A C37B C38B C39B C40B DFIX 1.41 0.003 O10 C41 O10 C44 DFIX 1.50 0.003 C41 C42 C42 C43 C43 C44 SIMU 0.003 O10 C41 C42 C43 C44 O11 O12 BOND $H CONF EQIV $1 -X+2, -Y+1, -Z EQIV $2 -X+2, -Y, -Z EQIV $3 X+1, Y-1, Z HTAB O1 O4_$1 HTAB O3 O2_$1 HTAB O5 O6_$2 HTAB O7 O9B_$3 HTAB O7 O9A_$3 L.S. 20 ACTA 52 WGHT 0.062800 0.735600 FVAR 3.02509 BR1 4 0.354581 0.978681 0.115716 11.00000 0.02724 0.02507 = 0.03214 0.00421 0.00737 0.01266 BR2 4 0.800976 0.884768 0.504020 11.00000 0.03925 0.02349 = 0.01981 -0.00069 0.00242 0.01156 BR3 4 0.437264 0.348937 0.170557 11.00000 0.02020 0.02625 = 0.03449 0.01001 0.00447 0.00722 BR4 4 1.145964 0.789899 0.490280 11.00000 0.04368 0.01611 = 0.02711 -0.00216 0.00430 0.00668 O1 3 0.806923 0.542249 -0.104494 11.00000 0.03131 0.03072 = 0.02220 0.00350 0.00827 0.00775 AFIX 83 H1 2 0.816373 0.474769 -0.126598 11.00000 -1.20000 AFIX 0 O2 3 0.818246 0.454273 0.005575 11.00000 0.02864 0.02388 = 0.02783 0.00587 0.01068 0.00751 O3 3 1.055578 0.704084 0.033718 11.00000 0.02327 0.03201 = 0.03072 0.00852 0.01177 0.00935 AFIX 147 H3 2 1.109588 0.666331 0.026812 11.00000 -1.20000 AFIX 0 O4 3 1.073070 0.631896 0.150795 11.00000 0.02604 0.03445 = 0.02834 0.00949 0.00582 0.01255 O5 3 1.115712 0.123801 0.074572 11.00000 0.02063 0.02049 = 0.02074 -0.00235 0.00661 0.00026 AFIX 83 H5 2 1.104921 0.066238 0.033790 11.00000 -1.20000 AFIX 0 O6 3 0.913062 0.032518 0.063402 11.00000 0.02199 0.02179 = 0.02109 -0.00471 0.00607 -0.00367 O7 3 1.293880 0.155840 0.316511 11.00000 0.02825 0.02971 = 0.03518 0.00083 -0.00332 0.01326 AFIX 83 H7 2 1.318792 0.092505 0.321942 11.00000 -1.20000 AFIX 0 O8 3 1.122414 0.018025 0.229627 11.00000 0.02716 0.01918 = 0.03385 0.00347 0.00493 0.00428 PART 1 O9A 3 0.386843 0.989615 0.378467 10.75000 0.03532 0.03979 = 0.03209 0.00916 0.00618 0.01788 PART 2 O9B 3 0.367324 0.963193 0.350341 10.25000 0.03891 0.03520 = 0.03603 0.01008 -0.00558 0.01170 PART 1 O10 3 0.547080 0.430966 0.430373 10.40000 0.07092 PART 0 C1 1 0.503101 0.676452 0.106876 11.00000 0.02394 0.01554 = 0.02449 0.00699 0.00690 0.00136 AFIX 43 H1A 2 0.478557 0.594406 0.114914 11.00000 -1.20000 AFIX 0 C2 1 0.426494 0.754128 0.116353 11.00000 0.01904 0.02254 = 0.02493 0.00369 0.00653 0.00099 AFIX 43 H2 2 0.349860 0.725213 0.130411 11.00000 -1.20000 AFIX 0 C3 1 0.462056 0.874055 0.105257 11.00000 0.02192 0.01849 = 0.01833 -0.00101 0.00153 0.00695 C4 1 0.573483 0.917363 0.084920 11.00000 0.02343 0.01724 = 0.02990 0.00795 0.00833 0.00587 AFIX 43 H4 2 0.597431 0.999654 0.077208 11.00000 -1.20000 AFIX 0 C5 1 0.650149 0.838678 0.075895 11.00000 0.01802 0.02355 = 0.03377 0.01177 0.00837 0.00155 AFIX 43 H5A 2 0.727387 0.868549 0.062797 11.00000 -1.20000 AFIX 0 C6 1 0.615740 0.716630 0.085720 11.00000 0.01885 0.01639 = 0.01897 0.00422 0.00285 0.00458 C7 1 0.695766 0.628471 0.076914 11.00000 0.01677 0.01862 = 0.02205 0.00527 0.00701 0.00405 AFIX 13 H7A 2 0.644003 0.540427 0.060540 11.00000 -1.20000 AFIX 0 C8 1 0.787099 0.656533 0.020401 11.00000 0.01899 0.02369 = 0.02206 0.00992 0.00668 0.00641 AFIX 13 H8 2 0.769252 0.717630 -0.014318 11.00000 -1.20000 AFIX 0 C9 1 0.804309 0.541280 -0.026704 11.00000 0.01365 0.02991 = 0.02149 0.00063 0.00484 0.00049 C10 1 0.750155 0.640406 0.283237 11.00000 0.03457 0.01613 = 0.02580 0.00118 0.00808 -0.00081 AFIX 43 H10 2 0.706904 0.556101 0.259469 11.00000 -1.20000 AFIX 0 C11 1 0.746252 0.691493 0.362757 11.00000 0.03406 0.01849 = 0.02371 0.00336 0.00925 -0.00367 AFIX 43 H11 2 0.700442 0.643156 0.392928 11.00000 -1.20000 AFIX 0 C12 1 0.809896 0.813030 0.396641 11.00000 0.02529 0.01757 = 0.01521 -0.00222 0.00017 0.00753 C13 1 0.876745 0.883995 0.353988 11.00000 0.02928 0.01487 = 0.03184 -0.00208 0.00319 -0.00123 AFIX 43 H13 2 0.920601 0.967897 0.378638 11.00000 -1.20000 AFIX 0 C14 1 0.880019 0.832426 0.274320 11.00000 0.03073 0.01839 = 0.02704 0.00723 0.01036 0.00257 AFIX 43 H14 2 0.926448 0.881416 0.244770 11.00000 -1.20000 AFIX 0 C15 1 0.815797 0.709758 0.237782 11.00000 0.01760 0.01691 = 0.02154 0.00498 0.00510 0.00571 C16 1 0.815197 0.648390 0.152453 11.00000 0.01854 0.01818 = 0.02122 0.00573 0.00603 0.00546 AFIX 13 H16 2 0.832255 0.566304 0.155360 11.00000 -1.20000 AFIX 0 C17 1 0.897181 0.712727 0.101830 11.00000 0.02058 0.01729 = 0.02171 0.00807 0.00600 0.00475 AFIX 13 H17 2 0.912166 0.804442 0.117180 11.00000 -1.20000 AFIX 0 C18 1 1.018092 0.680262 0.100188 11.00000 0.01911 0.01631 = 0.02571 0.00238 0.00375 0.00032 C19 1 0.753064 0.244038 0.275017 11.00000 0.02394 0.03154 = 0.01934 0.01155 0.00284 0.01072 AFIX 43 H19 2 0.789527 0.228748 0.327526 11.00000 -1.20000 AFIX 0 C20 1 0.642131 0.279258 0.263640 11.00000 0.02707 0.03243 = 0.02206 0.00767 0.00965 0.00781 AFIX 43 H20 2 0.603034 0.288873 0.307706 11.00000 -1.20000 AFIX 0 C21 1 0.589324 0.300207 0.186324 11.00000 0.01446 0.01724 = 0.02414 0.00349 0.00067 0.00321 C22 1 0.645023 0.287680 0.122321 11.00000 0.02573 0.01974 = 0.01788 0.00357 -0.00129 0.00251 AFIX 43 H22 2 0.607912 0.302715 0.069867 11.00000 -1.20000 AFIX 0 C23 1 0.757236 0.252459 0.135315 11.00000 0.02292 0.01907 = 0.01932 0.00343 0.00737 0.00224 AFIX 43 H23 2 0.796222 0.243464 0.091146 11.00000 -1.20000 AFIX 0 C24 1 0.812620 0.230425 0.211595 11.00000 0.01747 0.01268 = 0.01753 -0.00069 0.00086 -0.00039 C25 1 0.929091 0.186107 0.225893 11.00000 0.02302 0.01291 = 0.01508 0.00211 0.00512 0.00186 AFIX 13 H25 2 0.903532 0.095095 0.223266 11.00000 -1.20000 AFIX 0 C26 1 1.022856 0.210953 0.172088 11.00000 0.01813 0.01311 = 0.01815 0.00194 0.00178 0.00144 AFIX 13 H26 2 1.021995 0.290510 0.153759 11.00000 -1.20000 AFIX 0 C27 1 1.011885 0.112059 0.098734 11.00000 0.02113 0.01871 = 0.01664 0.00511 0.00363 0.00398 C28 1 1.106901 0.412772 0.435451 11.00000 0.03359 0.02050 = 0.01816 0.00565 0.00503 0.01045 AFIX 43 H28 2 1.120886 0.351141 0.465904 11.00000 -1.20000 AFIX 0 C29 1 1.133030 0.533348 0.477589 11.00000 0.03587 0.02456 = 0.01616 0.00136 0.00325 0.01046 AFIX 43 H29 2 1.165817 0.554670 0.536347 11.00000 -1.20000 AFIX 0 C30 1 1.111368 0.622285 0.434108 11.00000 0.02258 0.01572 = 0.02314 -0.00074 0.00479 0.00240 C31 1 1.064042 0.593582 0.348537 11.00000 0.03097 0.01982 = 0.02364 0.00603 -0.00253 0.00822 AFIX 43 H31 2 1.048960 0.655923 0.319032 11.00000 -1.20000 AFIX 0 C32 1 1.039125 0.472601 0.306793 11.00000 0.03211 0.02009 = 0.01745 0.00178 -0.00363 0.00483 AFIX 43 H32 2 1.006804 0.452345 0.247999 11.00000 -1.20000 AFIX 0 C33 1 1.060272 0.378957 0.348897 11.00000 0.01827 0.01551 = 0.01752 0.00080 0.00275 0.00337 C34 1 1.041588 0.247414 0.305984 11.00000 0.01830 0.01640 = 0.01660 0.00400 0.00301 0.00518 AFIX 13 H34 2 1.045919 0.191996 0.346665 11.00000 -1.20000 AFIX 0 C35 1 1.134600 0.233810 0.249738 11.00000 0.01727 0.01965 = 0.01807 -0.00048 0.00230 0.00220 AFIX 13 H35 2 1.202584 0.311128 0.256893 11.00000 -1.20000 AFIX 0 C36 1 1.182002 0.123439 0.261848 11.00000 0.02134 0.02370 = 0.01999 0.00349 0.00727 0.00729 PART 1 C37A 1 0.517855 1.046973 0.398613 10.75000 0.03320 0.04099 = 0.03746 0.00919 0.00309 0.01425 AFIX 23 H37A 2 0.558429 1.047550 0.457083 10.75000 -1.20000 H37B 2 0.533513 1.133256 0.390856 10.75000 -1.20000 PART 2 AFIX 0 C37B 1 0.491216 0.954332 0.355838 10.25000 0.03780 0.04302 = 0.03971 0.00943 0.00367 0.01806 AFIX 23 H37C 2 0.547713 1.002717 0.410169 10.25000 -1.20000 H37D 2 0.522094 0.988278 0.311246 10.25000 -1.20000 PART 1 AFIX 0 C38A 1 0.567812 0.970874 0.340082 10.75000 0.03872 0.05414 = 0.03244 0.01356 0.00728 0.02020 AFIX 23 H38A 2 0.658308 0.978583 0.362921 10.75000 -1.20000 H38B 2 0.554285 0.993104 0.284881 10.75000 -1.20000 PART 2 AFIX 0 C38B 1 0.491236 0.820856 0.347003 10.25000 0.03908 0.03914 = 0.03932 0.00867 0.00139 0.02373 AFIX 23 H38C 2 0.542538 0.806552 0.398478 10.25000 -1.20000 H38D 2 0.524613 0.794057 0.299803 10.25000 -1.20000 PART 1 AFIX 0 C39A 1 0.487860 0.844184 0.336153 10.75000 0.04631 0.04675 = 0.03477 0.00364 0.00336 0.02103 AFIX 23 H39A 2 0.520481 0.811619 0.385304 10.75000 -1.20000 H39B 2 0.483678 0.785708 0.285043 10.75000 -1.20000 PART 2 AFIX 0 C39B 1 0.355242 0.753388 0.331300 10.25000 0.03622 0.03596 = 0.03509 0.01278 0.00321 0.02144 AFIX 23 H39C 2 0.330810 0.679770 0.285357 10.25000 -1.20000 H39D 2 0.338215 0.726790 0.381850 10.25000 -1.20000 PART 1 AFIX 0 C40A 1 0.361325 0.865724 0.335408 10.75000 0.04186 0.03932 = 0.03737 0.00743 0.00445 0.01108 AFIX 23 H40A 2 0.309997 0.853774 0.277615 10.75000 -1.20000 H40B 2 0.315446 0.808033 0.363790 10.75000 -1.20000 PART 2 AFIX 0 C40B 1 0.285637 0.846349 0.308226 10.25000 0.03402 0.02999 = 0.02899 0.00987 -0.00012 0.00957 AFIX 23 H40C 2 0.264780 0.840472 0.247328 10.25000 -1.20000 H40D 2 0.206644 0.832244 0.325818 10.25000 -1.20000 PART 1 AFIX 0 C41 1 0.537566 0.394347 0.505688 10.40000 0.06731 C42 1 0.543501 0.515817 0.558459 10.40000 0.07629 C43 1 0.491335 0.585451 0.496295 10.40000 0.07497 C44 1 0.460526 0.501474 0.412346 10.40000 0.07203 PART 2 O11 3 0.422872 0.562667 0.396152 10.20000 0.07408 O12 3 0.521548 0.563346 0.550409 10.20000 0.07970 HKLF 4 REM testa in P-1 REM R1 = 0.0459 for 7972 Fo > 4sig(Fo) and 0.0629 for all 9966 data REM 552 parameters refined using 156 restraints END WGHT 0.0628 0.7356 REM Highest difference peak 1.408, deepest hole -0.825, 1-sigma level 0.123 Q1 1 1.2052 0.7640 0.5017 11.00000 0.05 1.41 Q2 1 0.5023 0.3188 0.1714 11.00000 0.05 1.27 Q3 1 0.2918 0.6030 0.2471 11.00000 0.05 1.12 Q4 1 0.8526 0.8475 0.5213 11.00000 0.05 1.11 Q5 1 0.7382 0.9186 0.4940 11.00000 0.05 1.09 Q6 1 1.1065 0.7678 0.5228 11.00000 0.05 1.07 Q7 1 0.4169 0.9491 0.1223 11.00000 0.05 1.06 Q8 1 0.3763 0.3827 0.1625 11.00000 0.05 0.99 Q9 1 0.3013 1.0185 0.1073 11.00000 0.05 0.93 Q10 1 0.4403 0.3057 0.2086 11.00000 0.05 0.88 Q11 1 0.3537 0.9329 0.1586 11.00000 0.05 0.87 Q12 1 0.7515 0.8501 0.5432 11.00000 0.05 0.86 Q13 1 1.1397 0.8426 0.4565 11.00000 0.05 0.83 Q14 1 0.5416 0.3595 0.5155 11.00000 0.05 0.81 Q15 1 1.0859 0.8331 0.4782 11.00000 0.05 0.81 Q16 1 0.4182 0.4008 0.1326 11.00000 0.05 0.80 Q17 1 0.7612 0.5878 -0.1185 11.00000 0.05 0.79 Q18 1 0.3979 1.0049 0.0803 11.00000 0.05 0.76 Q19 1 0.5229 0.4601 0.4054 11.00000 0.05 0.76 Q20 1 0.8574 0.8975 0.4771 11.00000 0.05 0.74 ; _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20.80 H18 Br2 O4.90' _chemical_formula_sum 'C20.80 H18 Br2 O4.90' _chemical_formula_weight 506.17 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' 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' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 11.3180(4) _cell_length_b 11.3592(4) _cell_length_c 16.8666(6) _cell_angle_alpha 98.753(3) _cell_angle_beta 102.761(3) _cell_angle_gamma 103.029(3) _cell_volume 2013.34(12) _cell_formula_units_Z 4 _cell_measurement_temperature 120(2) _cell_measurement_reflns_used 6260 _cell_measurement_theta_min 2.5565 _cell_measurement_theta_max 30.5730 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.18 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.670 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1008 _exptl_absorpt_coefficient_mu 4.055 _exptl_absorpt_correction_type analytical _exptl_absorpt_correction_T_min 0.659 _exptl_absorpt_correction_T_max 0.742 _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET) (compiled Jan 20 2011,15:58:25) 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_special_details ; ? ; _diffrn_ambient_temperature 120(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'Enhance (Mo) X-ray Source' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Xcalibur, Sapphire3, Gemini ultra' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean 16.1511 _diffrn_reflns_number 18052 _diffrn_reflns_av_R_equivalents 0.0354 _diffrn_reflns_av_sigmaI/netI 0.0546 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_theta_min 2.56 _diffrn_reflns_theta_max 28.28 _reflns_number_total 9966 _reflns_number_gt 7972 _reflns_threshold_expression >2sigma(I) _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET) (compiled Jan 20 2011,15:58:25) ; _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET) (compiled Jan 20 2011,15:58:25) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.34.49 (release 20-01-2011 CrysAlis171 .NET) (compiled Jan 20 2011,15:58:25) ; _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'ORTEP3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _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^)+(0.0628P)^2^+0.7356P] 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 9966 _refine_ls_number_parameters 552 _refine_ls_number_restraints 156 _refine_ls_R_factor_all 0.0629 _refine_ls_R_factor_gt 0.0459 _refine_ls_wR_factor_ref 0.1198 _refine_ls_wR_factor_gt 0.1095 _refine_ls_goodness_of_fit_ref 1.035 _refine_ls_restrained_S_all 1.031 _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 0.35458(3) 0.97868(3) 0.11572(2) 0.02750(10) Uani 1 1 d . . . Br2 Br 0.80098(4) 0.88477(3) 0.50402(2) 0.02847(10) Uani 1 1 d . . . Br3 Br 0.43726(3) 0.34894(3) 0.17056(2) 0.02688(10) Uani 1 1 d . . . Br4 Br 1.14596(4) 0.78990(3) 0.49028(2) 0.03078(10) Uani 1 1 d . . . O1 O 0.8069(2) 0.5422(2) -0.10449(14) 0.0282(5) Uani 1 1 d . . . H1 H 0.8164 0.4748 -0.1266 0.034 Uiso 1 1 calc R . . O2 O 0.8182(2) 0.4543(2) 0.00557(15) 0.0261(5) Uani 1 1 d . . . O3 O 1.0556(2) 0.7041(2) 0.03372(15) 0.0274(5) Uani 1 1 d . . . H3 H 1.1096 0.6663 0.0268 0.033 Uiso 1 1 calc R . . O4 O 1.0731(2) 0.6319(2) 0.15079(15) 0.0288(6) Uani 1 1 d . . . O5 O 1.1157(2) 0.1238(2) 0.07457(14) 0.0221(5) Uani 1 1 d . . . H5 H 1.1049 0.0662 0.0338 0.026 Uiso 1 1 calc R . . O6 O 0.9131(2) 0.0325(2) 0.06340(14) 0.0242(5) Uani 1 1 d . . . O7 O 1.2939(2) 0.1558(2) 0.31651(16) 0.0327(6) Uani 1 1 d . . . H7 H 1.3188 0.0925 0.3219 0.039 Uiso 1 1 calc R . . O8 O 1.1224(2) 0.0180(2) 0.22963(16) 0.0278(5) Uani 1 1 d . . . O9A O 0.3868(4) 0.9896(4) 0.3785(3) 0.0347(10) Uani 0.75 1 d PDU A 1 O9B O 0.3673(11) 0.9632(13) 0.3503(9) 0.039(3) Uani 0.25 1 d PDU B 2 O10 O 0.5471(10) 0.4310(10) 0.4304(6) 0.071(2) Uiso 0.40 1 d PDU . 1 C1 C 0.5031(3) 0.6765(3) 0.1069(2) 0.0216(7) Uani 1 1 d . . . H1A H 0.4786 0.5944 0.1149 0.026 Uiso 1 1 calc R . . C2 C 0.4265(3) 0.7541(3) 0.1164(2) 0.0230(7) Uani 1 1 d . . . H2 H 0.3499 0.7252 0.1304 0.028 Uiso 1 1 calc R . . C3 C 0.4621(3) 0.8741(3) 0.10526(19) 0.0205(7) Uani 1 1 d . . . C4 C 0.5735(3) 0.9174(3) 0.0849(2) 0.0229(7) Uani 1 1 d . . . H4 H 0.5974 0.9997 0.0772 0.028 Uiso 1 1 calc R . . C5 C 0.6501(3) 0.8387(3) 0.0759(2) 0.0249(7) Uani 1 1 d . . . H5A H 0.7274 0.8685 0.0628 0.030 Uiso 1 1 calc R . . C6 C 0.6157(3) 0.7166(3) 0.08572(19) 0.0184(6) Uani 1 1 d . . . C7 C 0.6958(3) 0.6285(3) 0.07691(19) 0.0189(6) Uani 1 1 d . . . H7A H 0.6440 0.5404 0.0605 0.023 Uiso 1 1 calc R . . C8 C 0.7871(3) 0.6565(3) 0.0204(2) 0.0207(7) Uani 1 1 d . . . H8 H 0.7693 0.7176 -0.0143 0.025 Uiso 1 1 calc R . . C9 C 0.8043(3) 0.5413(3) -0.0267(2) 0.0231(7) Uani 1 1 d . . . C10 C 0.7502(4) 0.6404(3) 0.2832(2) 0.0271(8) Uani 1 1 d . . . H10 H 0.7069 0.5561 0.2595 0.033 Uiso 1 1 calc R . . C11 C 0.7463(3) 0.6915(3) 0.3628(2) 0.0271(8) Uani 1 1 d . . . H11 H 0.7004 0.6432 0.3929 0.033 Uiso 1 1 calc R . . C12 C 0.8099(3) 0.8130(3) 0.39664(19) 0.0206(7) Uani 1 1 d . . . C13 C 0.8767(3) 0.8840(3) 0.3540(2) 0.0281(8) Uani 1 1 d . . . H13 H 0.9206 0.9679 0.3786 0.034 Uiso 1 1 calc R . . C14 C 0.8800(3) 0.8324(3) 0.2743(2) 0.0254(7) Uani 1 1 d . . . H14 H 0.9264 0.8814 0.2448 0.030 Uiso 1 1 calc R . . C15 C 0.8158(3) 0.7098(3) 0.23778(19) 0.0184(6) Uani 1 1 d . . . C16 C 0.8152(3) 0.6484(3) 0.15245(19) 0.0189(6) Uani 1 1 d . . . H16 H 0.8323 0.5663 0.1554 0.023 Uiso 1 1 calc R . . C17 C 0.8972(3) 0.7127(3) 0.10183(19) 0.0194(6) Uani 1 1 d . . . H17 H 0.9122 0.8044 0.1172 0.023 Uiso 1 1 calc R . . C18 C 1.0181(3) 0.6803(3) 0.1002(2) 0.0217(7) Uani 1 1 d . . . C19 C 0.7531(3) 0.2440(3) 0.2750(2) 0.0242(7) Uani 1 1 d . . . H19 H 0.7895 0.2287 0.3275 0.029 Uiso 1 1 calc R . . C20 C 0.6421(3) 0.2793(3) 0.2636(2) 0.0265(8) Uani 1 1 d . . . H20 H 0.6030 0.2889 0.3077 0.032 Uiso 1 1 calc R . . C21 C 0.5893(3) 0.3002(3) 0.1863(2) 0.0196(6) Uani 1 1 d . . . C22 C 0.6450(3) 0.2877(3) 0.1223(2) 0.0229(7) Uani 1 1 d . . . H22 H 0.6079 0.3027 0.0699 0.028 Uiso 1 1 calc R . . C23 C 0.7572(3) 0.2525(3) 0.1353(2) 0.0208(7) Uani 1 1 d . . . H23 H 0.7962 0.2435 0.0911 0.025 Uiso 1 1 calc R . . C24 C 0.8126(3) 0.2304(3) 0.21160(19) 0.0177(6) Uani 1 1 d . . . C25 C 0.9291(3) 0.1861(3) 0.22589(18) 0.0176(6) Uani 1 1 d . . . H25 H 0.9035 0.0951 0.2233 0.021 Uiso 1 1 calc R . . C26 C 1.0229(3) 0.2110(3) 0.17209(19) 0.0176(6) Uani 1 1 d . . . H26 H 1.0220 0.2905 0.1538 0.021 Uiso 1 1 calc R . . C27 C 1.0119(3) 0.1121(3) 0.09873(19) 0.0191(6) Uani 1 1 d . . . C28 C 1.1069(3) 0.4128(3) 0.4355(2) 0.0237(7) Uani 1 1 d . . . H28 H 1.1209 0.3511 0.4659 0.028 Uiso 1 1 calc R . . C29 C 1.1330(4) 0.5333(3) 0.4776(2) 0.0261(7) Uani 1 1 d . . . H29 H 1.1658 0.5547 0.5363 0.031 Uiso 1 1 calc R . . C30 C 1.1114(3) 0.6223(3) 0.4341(2) 0.0217(7) Uani 1 1 d . . . C31 C 1.0640(3) 0.5936(3) 0.3485(2) 0.0260(8) Uani 1 1 d . . . H31 H 1.0490 0.6559 0.3190 0.031 Uiso 1 1 calc R . . C32 C 1.0391(3) 0.4726(3) 0.3068(2) 0.0255(7) Uani 1 1 d . . . H32 H 1.0068 0.4523 0.2480 0.031 Uiso 1 1 calc R . . C33 C 1.0603(3) 0.3790(3) 0.34890(19) 0.0179(6) Uani 1 1 d . . . C34 C 1.0416(3) 0.2474(3) 0.30598(19) 0.0172(6) Uani 1 1 d . . . H34 H 1.0459 0.1920 0.3467 0.021 Uiso 1 1 calc R . . C35 C 1.1346(3) 0.2338(3) 0.24974(19) 0.0197(6) Uani 1 1 d . . . H35 H 1.2026 0.3111 0.2569 0.024 Uiso 1 1 calc R . . C36 C 1.1820(3) 0.1234(3) 0.2618(2) 0.0213(7) Uani 1 1 d . . . C37A C 0.5179(4) 1.0470(5) 0.3986(3) 0.0374(12) Uani 0.75 1 d PDU A 1 H37A H 0.5584 1.0475 0.4571 0.045 Uiso 0.75 1 calc PR A 1 H37B H 0.5335 1.1333 0.3909 0.045 Uiso 0.75 1 calc PR A 1 C37B C 0.4912(13) 0.9543(15) 0.3558(11) 0.040(2) Uani 0.25 1 d PDU B 2 H37C H 0.5477 1.0027 0.4102 0.048 Uiso 0.25 1 calc PR B 2 H37D H 0.5221 0.9883 0.3112 0.048 Uiso 0.25 1 calc PR B 2 C38A C 0.5678(5) 0.9709(5) 0.3401(3) 0.0403(12) Uani 0.75 1 d PDU A 1 H38A H 0.6583 0.9786 0.3629 0.048 Uiso 0.75 1 calc PR A 1 H38B H 0.5543 0.9931 0.2849 0.048 Uiso 0.75 1 calc PR A 1 C38B C 0.4912(14) 0.8209(14) 0.347(2) 0.038(3) Uani 0.25 1 d PDU B 2 H38C H 0.5425 0.8066 0.3985 0.046 Uiso 0.25 1 calc PR B 2 H38D H 0.5246 0.7941 0.2998 0.046 Uiso 0.25 1 calc PR B 2 C39A C 0.4879(5) 0.8442(6) 0.3362(7) 0.0430(18) Uani 0.75 1 d PDU A 1 H39A H 0.5205 0.8116 0.3853 0.052 Uiso 0.75 1 calc PR A 1 H39B H 0.4837 0.7857 0.2850 0.052 Uiso 0.75 1 calc PR A 1 C39B C 0.3552(12) 0.7534(13) 0.3313(10) 0.034(2) Uani 0.25 1 d PDU B 2 H39C H 0.3308 0.6798 0.2854 0.041 Uiso 0.25 1 calc PR B 2 H39D H 0.3382 0.7268 0.3819 0.041 Uiso 0.25 1 calc PR B 2 C40A C 0.3613(5) 0.8657(4) 0.3354(3) 0.0406(12) Uani 0.75 1 d PDU A 1 H40A H 0.3100 0.8538 0.2776 0.049 Uiso 0.75 1 calc PR A 1 H40B H 0.3154 0.8080 0.3638 0.049 Uiso 0.75 1 calc PR A 1 C40B C 0.2856(13) 0.8463(10) 0.3082(9) 0.032(3) Uani 0.25 1 d PDU B 2 H40C H 0.2648 0.8405 0.2473 0.038 Uiso 0.25 1 calc PR B 2 H40D H 0.2066 0.8322 0.3258 0.038 Uiso 0.25 1 calc PR B 2 C41 C 0.5376(17) 0.3943(14) 0.5057(7) 0.067(2) Uiso 0.40 1 d PDU . 1 C42 C 0.5435(19) 0.5158(14) 0.5585(9) 0.076(2) Uiso 0.40 1 d PDU . 1 C43 C 0.4913(18) 0.5855(16) 0.4963(8) 0.075(2) Uiso 0.40 1 d PDU . 1 C44 C 0.4605(15) 0.5015(15) 0.4123(9) 0.072(2) Uiso 0.40 1 d PDU . 1 O11 O 0.423(2) 0.563(2) 0.3962(13) 0.074(3) Uiso 0.20 1 d PU C 2 O12 O 0.522(3) 0.563(2) 0.5504(14) 0.080(3) Uiso 0.20 1 d PU D 2 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 0.02724(19) 0.02507(18) 0.03214(19) 0.00421(15) 0.00737(14) 0.01266(15) Br2 0.0393(2) 0.02349(18) 0.01981(17) -0.00069(14) 0.00242(14) 0.01156(16) Br3 0.02020(17) 0.02625(19) 0.03449(19) 0.01001(15) 0.00447(14) 0.00722(14) Br4 0.0437(2) 0.01611(17) 0.02711(19) -0.00216(14) 0.00430(16) 0.00668(15) O1 0.0313(14) 0.0307(14) 0.0222(12) 0.0035(11) 0.0083(10) 0.0077(11) O2 0.0286(13) 0.0239(13) 0.0278(12) 0.0059(11) 0.0107(10) 0.0075(11) O3 0.0233(13) 0.0320(14) 0.0307(13) 0.0085(12) 0.0118(10) 0.0094(11) O4 0.0260(13) 0.0344(14) 0.0283(13) 0.0095(12) 0.0058(10) 0.0126(11) O5 0.0206(12) 0.0205(12) 0.0207(11) -0.0023(10) 0.0066(9) 0.0003(10) O6 0.0220(12) 0.0218(12) 0.0211(11) -0.0047(10) 0.0061(9) -0.0037(10) O7 0.0283(14) 0.0297(14) 0.0352(14) 0.0008(12) -0.0033(11) 0.0133(12) O8 0.0272(13) 0.0192(12) 0.0339(13) 0.0035(11) 0.0049(10) 0.0043(10) O9A 0.035(2) 0.040(2) 0.032(2) 0.0092(19) 0.0062(18) 0.0179(18) O9B 0.039(4) 0.035(5) 0.036(5) 0.010(4) -0.006(4) 0.012(4) C1 0.0239(17) 0.0155(15) 0.0245(16) 0.0070(13) 0.0069(13) 0.0014(13) C2 0.0190(16) 0.0225(17) 0.0249(16) 0.0037(14) 0.0065(13) 0.0010(13) C3 0.0219(16) 0.0185(16) 0.0183(15) -0.0010(13) 0.0015(12) 0.0070(13) C4 0.0234(17) 0.0172(16) 0.0299(17) 0.0080(14) 0.0083(14) 0.0059(13) C5 0.0180(16) 0.0235(17) 0.0338(19) 0.0118(16) 0.0084(14) 0.0015(14) C6 0.0188(16) 0.0164(15) 0.0190(15) 0.0042(13) 0.0029(12) 0.0046(13) C7 0.0168(15) 0.0186(16) 0.0221(15) 0.0053(13) 0.0070(12) 0.0041(13) C8 0.0190(16) 0.0237(17) 0.0221(15) 0.0099(14) 0.0067(12) 0.0064(13) C9 0.0136(15) 0.0299(19) 0.0215(16) 0.0006(15) 0.0048(12) 0.0005(14) C10 0.035(2) 0.0161(16) 0.0258(17) 0.0012(14) 0.0081(15) -0.0008(15) C11 0.034(2) 0.0185(17) 0.0237(17) 0.0034(14) 0.0093(15) -0.0037(15) C12 0.0253(17) 0.0176(16) 0.0152(14) -0.0022(13) 0.0002(12) 0.0075(13) C13 0.0293(19) 0.0149(16) 0.0318(19) -0.0021(15) 0.0032(15) -0.0012(14) C14 0.0307(19) 0.0184(16) 0.0270(17) 0.0072(14) 0.0104(14) 0.0026(14) C15 0.0176(15) 0.0169(15) 0.0215(15) 0.0050(13) 0.0051(12) 0.0057(12) C16 0.0185(16) 0.0182(15) 0.0212(15) 0.0057(13) 0.0060(12) 0.0055(13) C17 0.0206(16) 0.0173(15) 0.0217(15) 0.0081(13) 0.0060(13) 0.0048(13) C18 0.0191(16) 0.0163(16) 0.0257(16) 0.0024(14) 0.0038(13) 0.0003(13) C19 0.0239(17) 0.0315(19) 0.0193(16) 0.0116(15) 0.0028(13) 0.0107(15) C20 0.0271(18) 0.032(2) 0.0221(16) 0.0077(15) 0.0097(14) 0.0078(16) C21 0.0145(15) 0.0172(15) 0.0241(16) 0.0035(13) 0.0007(12) 0.0032(12) C22 0.0257(18) 0.0197(16) 0.0179(15) 0.0036(13) -0.0013(13) 0.0025(14) C23 0.0229(17) 0.0191(16) 0.0193(15) 0.0034(13) 0.0074(13) 0.0022(13) C24 0.0175(15) 0.0127(14) 0.0175(14) -0.0007(12) 0.0009(12) -0.0004(12) C25 0.0230(16) 0.0129(14) 0.0151(14) 0.0021(12) 0.0051(12) 0.0019(12) C26 0.0181(15) 0.0131(14) 0.0181(15) 0.0019(12) 0.0018(12) 0.0014(12) C27 0.0211(16) 0.0187(16) 0.0166(14) 0.0051(13) 0.0036(12) 0.0040(13) C28 0.0336(19) 0.0205(17) 0.0182(15) 0.0057(14) 0.0050(13) 0.0105(15) C29 0.036(2) 0.0246(18) 0.0162(15) 0.0014(14) 0.0033(14) 0.0105(15) C30 0.0226(17) 0.0157(15) 0.0231(16) -0.0007(13) 0.0048(13) 0.0024(13) C31 0.0310(19) 0.0198(17) 0.0236(17) 0.0060(14) -0.0025(14) 0.0082(15) C32 0.0321(19) 0.0201(17) 0.0174(15) 0.0018(14) -0.0036(13) 0.0048(15) C33 0.0183(15) 0.0155(15) 0.0175(15) 0.0008(13) 0.0027(12) 0.0034(12) C34 0.0183(15) 0.0164(15) 0.0166(14) 0.0040(12) 0.0030(12) 0.0052(12) C35 0.0173(15) 0.0197(16) 0.0181(15) -0.0005(13) 0.0023(12) 0.0022(13) C36 0.0213(16) 0.0237(17) 0.0200(15) 0.0035(14) 0.0073(13) 0.0073(14) C37A 0.033(3) 0.041(3) 0.037(3) 0.009(2) 0.003(2) 0.014(2) C37B 0.038(4) 0.043(4) 0.040(4) 0.009(4) 0.004(4) 0.018(4) C38A 0.039(3) 0.054(3) 0.032(2) 0.014(2) 0.007(2) 0.020(3) C38B 0.039(5) 0.039(5) 0.039(5) 0.009(5) 0.001(4) 0.024(4) C39A 0.046(3) 0.047(3) 0.035(3) 0.004(3) 0.003(2) 0.021(3) C39B 0.036(5) 0.036(5) 0.035(5) 0.013(4) 0.003(4) 0.021(4) C40A 0.042(3) 0.039(3) 0.037(3) 0.007(2) 0.004(2) 0.011(2) C40B 0.034(5) 0.030(5) 0.029(5) 0.010(4) 0.000(5) 0.010(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 C3 1.899(3) . ? Br2 C12 1.903(3) . ? Br3 C21 1.900(3) . ? Br4 C30 1.904(3) . ? O1 C9 1.321(4) . ? O1 H1 0.8400 . ? O2 C9 1.222(4) . ? O3 C18 1.327(4) . ? O3 H3 0.8400 . ? O4 C18 1.216(4) . ? O5 C27 1.312(4) . ? O5 H5 0.8400 . ? O6 C27 1.228(4) . ? O7 C36 1.327(4) . ? O7 H7 0.8400 . ? O8 C36 1.208(4) . ? O9A C40A 1.416(3) . ? O9A C37A 1.419(3) . ? O9B C40B 1.411(3) . ? O9B C37B 1.412(3) . ? O10 C44 1.411(3) . ? O10 C41 1.414(3) . ? C1 C2 1.385(5) . ? C1 C6 1.396(5) . ? C1 H1A 0.9500 . ? C2 C3 1.384(5) . ? C2 H2 0.9500 . ? C3 C4 1.383(5) . ? C4 C5 1.393(5) . ? C4 H4 0.9500 . ? C5 C6 1.399(5) . ? C5 H5A 0.9500 . ? C6 C7 1.506(4) . ? C7 C8 1.568(4) . ? C7 C16 1.586(4) . ? C7 H7A 1.0000 . ? C8 C9 1.500(5) . ? C8 C17 1.570(4) . ? C8 H8 1.0000 . ? C10 C15 1.390(5) . ? C10 C11 1.392(5) . ? C10 H10 0.9500 . ? C11 C12 1.372(5) . ? C11 H11 0.9500 . ? C12 C13 1.372(5) . ? C13 C14 1.394(5) . ? C13 H13 0.9500 . ? C14 C15 1.391(5) . ? C14 H14 0.9500 . ? C15 C16 1.498(4) . ? C16 C17 1.536(4) . ? C16 H16 1.0000 . ? C17 C18 1.500(5) . ? C17 H17 1.0000 . ? C19 C20 1.384(5) . ? C19 C24 1.392(5) . ? C19 H19 0.9500 . ? C20 C21 1.389(5) . ? C20 H20 0.9500 . ? C21 C22 1.370(5) . ? C22 C23 1.398(5) . ? C22 H22 0.9500 . ? C23 C24 1.387(4) . ? C23 H23 0.9500 . ? C24 C25 1.498(4) . ? C25 C26 1.548(4) . ? C25 C34 1.576(4) . ? C25 H25 1.0000 . ? C26 C27 1.501(4) . ? C26 C35 1.549(4) . ? C26 H26 1.0000 . ? C28 C29 1.377(5) . ? C28 C33 1.398(4) . ? C28 H28 0.9500 . ? C29 C30 1.370(5) . ? C29 H29 0.9500 . ? C30 C31 1.383(5) . ? C31 C32 1.381(5) . ? C31 H31 0.9500 . ? C32 C33 1.401(5) . ? C32 H32 0.9500 . ? C33 C34 1.504(4) . ? C34 C35 1.582(4) . ? C34 H34 1.0000 . ? C35 C36 1.495(4) . ? C35 H35 1.0000 . ? C37A C38A 1.500(3) . ? C37A H37A 0.9900 . ? C37A H37B 0.9900 . ? C37B C38B 1.501(3) . ? C37B H37C 0.9900 . ? C37B H37D 0.9900 . ? C38A C39A 1.501(3) . ? C38A H38A 0.9900 . ? C38A H38B 0.9900 . ? C38B C39B 1.501(3) . ? C38B H38C 0.9900 . ? C38B H38D 0.9900 . ? C39A C40A 1.504(3) . ? C39A H39A 0.9900 . ? C39A H39B 0.9900 . ? C39B C40B 1.501(3) . ? C39B H39C 0.9900 . ? C39B H39D 0.9900 . ? C40A H40A 0.9900 . ? C40A H40B 0.9900 . ? C40B H40C 0.9900 . ? C40B H40D 0.9900 . ? C41 C42 1.503(3) . ? C42 C43 1.504(3) . ? C43 C44 1.502(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 C9 O1 H1 109.5 . . ? C18 O3 H3 109.5 . . ? C27 O5 H5 109.5 . . ? C36 O7 H7 109.5 . . ? C40A O9A C37A 109.6(4) . . ? C40B O9B C37B 107.0(13) . . ? C44 O10 C41 107.3(12) . . ? C2 C1 C6 121.2(3) . . ? C2 C1 H1A 119.4 . . ? C6 C1 H1A 119.4 . . ? C3 C2 C1 119.7(3) . . ? C3 C2 H2 120.1 . . ? C1 C2 H2 120.1 . . ? C4 C3 C2 120.7(3) . . ? C4 C3 Br1 119.8(3) . . ? C2 C3 Br1 119.5(3) . . ? C3 C4 C5 119.1(3) . . ? C3 C4 H4 120.4 . . ? C5 C4 H4 120.4 . . ? C4 C5 C6 121.4(3) . . ? C4 C5 H5A 119.3 . . ? C6 C5 H5A 119.3 . . ? C1 C6 C5 117.9(3) . . ? C1 C6 C7 118.8(3) . . ? C5 C6 C7 123.2(3) . . ? C6 C7 C8 115.4(3) . . ? C6 C7 C16 116.2(3) . . ? C8 C7 C16 88.4(2) . . ? C6 C7 H7A 111.6 . . ? C8 C7 H7A 111.6 . . ? C16 C7 H7A 111.6 . . ? C9 C8 C7 112.6(3) . . ? C9 C8 C17 110.7(3) . . ? C7 C8 C17 88.1(2) . . ? C9 C8 H8 114.2 . . ? C7 C8 H8 114.2 . . ? C17 C8 H8 114.2 . . ? O2 C9 O1 122.6(3) . . ? O2 C9 C8 122.1(3) . . ? O1 C9 C8 115.2(3) . . ? C15 C10 C11 121.6(3) . . ? C15 C10 H10 119.2 . . ? C11 C10 H10 119.2 . . ? C12 C11 C10 118.6(3) . . ? C12 C11 H11 120.7 . . ? C10 C11 H11 120.7 . . ? C11 C12 C13 121.4(3) . . ? C11 C12 Br2 118.8(3) . . ? C13 C12 Br2 119.7(3) . . ? C12 C13 C14 119.7(3) . . ? C12 C13 H13 120.2 . . ? C14 C13 H13 120.2 . . ? C15 C14 C13 120.5(3) . . ? C15 C14 H14 119.8 . . ? C13 C14 H14 119.8 . . ? C10 C15 C14 118.2(3) . . ? C10 C15 C16 118.5(3) . . ? C14 C15 C16 123.3(3) . . ? C15 C16 C17 122.1(3) . . ? C15 C16 C7 119.5(3) . . ? C17 C16 C7 88.7(2) . . ? C15 C16 H16 108.3 . . ? C17 C16 H16 108.3 . . ? C7 C16 H16 108.3 . . ? C18 C17 C16 118.4(3) . . ? C18 C17 C8 115.4(3) . . ? C16 C17 C8 90.1(2) . . ? C18 C17 H17 110.5 . . ? C16 C17 H17 110.5 . . ? C8 C17 H17 110.5 . . ? O4 C18 O3 123.1(3) . . ? O4 C18 C17 124.9(3) . . ? O3 C18 C17 111.9(3) . . ? C20 C19 C24 121.8(3) . . ? C20 C19 H19 119.1 . . ? C24 C19 H19 119.1 . . ? C19 C20 C21 118.5(3) . . ? C19 C20 H20 120.8 . . ? C21 C20 H20 120.8 . . ? C22 C21 C20 121.5(3) . . ? C22 C21 Br3 119.9(2) . . ? C20 C21 Br3 118.6(3) . . ? C21 C22 C23 119.0(3) . . ? C21 C22 H22 120.5 . . ? C23 C22 H22 120.5 . . ? C24 C23 C22 121.1(3) . . ? C24 C23 H23 119.4 . . ? C22 C23 H23 119.4 . . ? C23 C24 C19 118.1(3) . . ? C23 C24 C25 122.2(3) . . ? C19 C24 C25 119.6(3) . . ? C24 C25 C26 121.2(3) . . ? C24 C25 C34 120.8(3) . . ? C26 C25 C34 88.8(2) . . ? C24 C25 H25 108.1 . . ? C26 C25 H25 108.1 . . ? C34 C25 H25 108.1 . . ? C27 C26 C25 118.6(3) . . ? C27 C26 C35 117.9(3) . . ? C25 C26 C35 90.2(2) . . ? C27 C26 H26 109.6 . . ? C25 C26 H26 109.6 . . ? C35 C26 H26 109.6 . . ? O6 C27 O5 124.3(3) . . ? O6 C27 C26 122.4(3) . . ? O5 C27 C26 113.2(3) . . ? C29 C28 C33 121.5(3) . . ? C29 C28 H28 119.2 . . ? C33 C28 H28 119.2 . . ? C30 C29 C28 119.5(3) . . ? C30 C29 H29 120.3 . . ? C28 C29 H29 120.3 . . ? C29 C30 C31 121.3(3) . . ? C29 C30 Br4 120.7(2) . . ? C31 C30 Br4 118.0(3) . . ? C32 C31 C30 118.8(3) . . ? C32 C31 H31 120.6 . . ? C30 C31 H31 120.6 . . ? C31 C32 C33 121.7(3) . . ? C31 C32 H32 119.1 . . ? C33 C32 H32 119.1 . . ? C28 C33 C32 117.2(3) . . ? C28 C33 C34 119.0(3) . . ? C32 C33 C34 123.7(3) . . ? C33 C34 C25 119.7(3) . . ? C33 C34 C35 113.1(3) . . ? C25 C34 C35 88.1(2) . . ? C33 C34 H34 111.3 . . ? C25 C34 H34 111.3 . . ? C35 C34 H34 111.3 . . ? C36 C35 C26 114.9(3) . . ? C36 C35 C34 109.0(3) . . ? C26 C35 C34 88.6(2) . . ? C36 C35 H35 113.9 . . ? C26 C35 H35 113.9 . . ? C34 C35 H35 113.9 . . ? O8 C36 O7 124.6(3) . . ? O8 C36 C35 124.0(3) . . ? O7 C36 C35 111.2(3) . . ? O9A C37A C38A 105.5(4) . . ? O9A C37A H37A 110.6 . . ? C38A C37A H37A 110.6 . . ? O9A C37A H37B 110.6 . . ? C38A C37A H37B 110.6 . . ? H37A C37A H37B 108.8 . . ? O9B C37B C38B 108.8(14) . . ? O9B C37B H37C 109.9 . . ? C38B C37B H37C 109.9 . . ? O9B C37B H37D 109.9 . . ? C38B C37B H37D 109.9 . . ? H37C C37B H37D 108.3 . . ? C37A C38A C39A 100.0(5) . . ? C37A C38A H38A 111.8 . . ? C39A C38A H38A 111.8 . . ? C37A C38A H38B 111.8 . . ? C39A C38A H38B 111.8 . . ? H38A C38A H38B 109.5 . . ? C37B C38B C39B 104.0(14) . . ? C37B C38B H38C 111.0 . . ? C39B C38B H38C 111.0 . . ? C37B C38B H38D 111.0 . . ? C39B C38B H38D 111.0 . . ? H38C C38B H38D 109.0 . . ? C38A C39A C40A 103.0(5) . . ? C38A C39A H39A 111.2 . . ? C40A C39A H39A 111.2 . . ? C38A C39A H39B 111.2 . . ? C40A C39A H39B 111.2 . . ? H39A C39A H39B 109.1 . . ? C40B C39B C38B 104.3(13) . . ? C40B C39B H39C 110.9 . . ? C38B C39B H39C 110.9 . . ? C40B C39B H39D 110.9 . . ? C38B C39B H39D 110.9 . . ? H39C C39B H39D 108.9 . . ? O9A C40A C39A 105.4(5) . . ? O9A C40A H40A 110.7 . . ? C39A C40A H40A 110.7 . . ? O9A C40A H40B 110.7 . . ? C39A C40A H40B 110.7 . . ? H40A C40A H40B 108.8 . . ? O9B C40B C39B 105.9(12) . . ? O9B C40B H40C 110.6 . . ? C39B C40B H40C 110.6 . . ? O9B C40B H40D 110.6 . . ? C39B C40B H40D 110.6 . . ? H40C C40B H40D 108.7 . . ? O10 C41 C42 100.3(10) . . ? C41 C42 C43 103.7(11) . . ? C44 C43 C42 106.0(12) . . ? O10 C44 C43 99.3(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 C6 C1 C2 C3 -0.4(5) . . . . ? C1 C2 C3 C4 -0.1(5) . . . . ? C1 C2 C3 Br1 178.5(2) . . . . ? C2 C3 C4 C5 -0.2(5) . . . . ? Br1 C3 C4 C5 -178.8(2) . . . . ? C3 C4 C5 C6 1.0(5) . . . . ? C2 C1 C6 C5 1.2(5) . . . . ? C2 C1 C6 C7 179.5(3) . . . . ? C4 C5 C6 C1 -1.5(5) . . . . ? C4 C5 C6 C7 -179.7(3) . . . . ? C1 C6 C7 C8 156.3(3) . . . . ? C5 C6 C7 C8 -25.4(4) . . . . ? C1 C6 C7 C16 -102.2(3) . . . . ? C5 C6 C7 C16 76.1(4) . . . . ? C6 C7 C8 C9 -145.8(3) . . . . ? C16 C7 C8 C9 95.7(3) . . . . ? C6 C7 C8 C17 102.4(3) . . . . ? C16 C7 C8 C17 -16.0(2) . . . . ? C7 C8 C9 O2 -42.5(4) . . . . ? C17 C8 C9 O2 54.3(4) . . . . ? C7 C8 C9 O1 139.4(3) . . . . ? C17 C8 C9 O1 -123.8(3) . . . . ? C15 C10 C11 C12 -0.5(6) . . . . ? C10 C11 C12 C13 -0.2(5) . . . . ? C10 C11 C12 Br2 178.2(3) . . . . ? C11 C12 C13 C14 0.3(5) . . . . ? Br2 C12 C13 C14 -178.0(3) . . . . ? C12 C13 C14 C15 0.2(5) . . . . ? C11 C10 C15 C14 1.0(5) . . . . ? C11 C10 C15 C16 -179.8(3) . . . . ? C13 C14 C15 C10 -0.8(5) . . . . ? C13 C14 C15 C16 180.0(3) . . . . ? C10 C15 C16 C17 -172.7(3) . . . . ? C14 C15 C16 C17 6.5(5) . . . . ? C10 C15 C16 C7 78.4(4) . . . . ? C14 C15 C16 C7 -102.4(4) . . . . ? C6 C7 C16 C15 25.4(4) . . . . ? C8 C7 C16 C15 143.1(3) . . . . ? C6 C7 C16 C17 -101.3(3) . . . . ? C8 C7 C16 C17 16.4(2) . . . . ? C15 C16 C17 C18 99.8(4) . . . . ? C7 C16 C17 C18 -135.6(3) . . . . ? C15 C16 C17 C8 -140.9(3) . . . . ? C7 C16 C17 C8 -16.4(2) . . . . ? C9 C8 C17 C18 24.9(4) . . . . ? C7 C8 C17 C18 138.4(3) . . . . ? C9 C8 C17 C16 -96.9(3) . . . . ? C7 C8 C17 C16 16.6(2) . . . . ? C16 C17 C18 O4 -19.5(5) . . . . ? C8 C17 C18 O4 -124.5(4) . . . . ? C16 C17 C18 O3 156.9(3) . . . . ? C8 C17 C18 O3 51.9(4) . . . . ? C24 C19 C20 C21 0.6(6) . . . . ? C19 C20 C21 C22 -0.5(5) . . . . ? C19 C20 C21 Br3 -179.9(3) . . . . ? C20 C21 C22 C23 0.3(5) . . . . ? Br3 C21 C22 C23 179.6(2) . . . . ? C21 C22 C23 C24 -0.1(5) . . . . ? C22 C23 C24 C19 0.2(5) . . . . ? C22 C23 C24 C25 176.7(3) . . . . ? C20 C19 C24 C23 -0.4(5) . . . . ? C20 C19 C24 C25 -177.0(3) . . . . ? C23 C24 C25 C26 24.7(4) . . . . ? C19 C24 C25 C26 -158.9(3) . . . . ? C23 C24 C25 C34 134.1(3) . . . . ? C19 C24 C25 C34 -49.5(4) . . . . ? C24 C25 C26 C27 -96.1(3) . . . . ? C34 C25 C26 C27 138.1(3) . . . . ? C24 C25 C26 C35 141.6(3) . . . . ? C34 C25 C26 C35 15.8(2) . . . . ? C25 C26 C27 O6 24.1(4) . . . . ? C35 C26 C27 O6 131.3(3) . . . . ? C25 C26 C27 O5 -159.1(3) . . . . ? C35 C26 C27 O5 -52.0(4) . . . . ? C33 C28 C29 C30 0.9(6) . . . . ? C28 C29 C30 C31 -0.2(6) . . . . ? C28 C29 C30 Br4 179.8(3) . . . . ? C29 C30 C31 C32 -0.3(6) . . . . ? Br4 C30 C31 C32 179.6(3) . . . . ? C30 C31 C32 C33 0.2(6) . . . . ? C29 C28 C33 C32 -1.1(5) . . . . ? C29 C28 C33 C34 176.0(3) . . . . ? C31 C32 C33 C28 0.5(5) . . . . ? C31 C32 C33 C34 -176.4(3) . . . . ? C28 C33 C34 C25 145.9(3) . . . . ? C32 C33 C34 C25 -37.2(5) . . . . ? C28 C33 C34 C35 -112.5(3) . . . . ? C32 C33 C34 C35 64.4(4) . . . . ? C24 C25 C34 C33 -26.0(4) . . . . ? C26 C25 C34 C33 100.2(3) . . . . ? C24 C25 C34 C35 -141.7(3) . . . . ? C26 C25 C34 C35 -15.4(2) . . . . ? C27 C26 C35 C36 -28.3(4) . . . . ? C25 C26 C35 C36 94.6(3) . . . . ? C27 C26 C35 C34 -138.7(3) . . . . ? C25 C26 C35 C34 -15.7(2) . . . . ? C33 C34 C35 C36 137.8(3) . . . . ? C25 C34 C35 C36 -100.5(3) . . . . ? C33 C34 C35 C26 -106.2(3) . . . . ? C25 C34 C35 C26 15.4(2) . . . . ? C26 C35 C36 O8 -19.0(5) . . . . ? C34 C35 C36 O8 78.5(4) . . . . ? C26 C35 C36 O7 165.1(3) . . . . ? C34 C35 C36 O7 -97.4(3) . . . . ? C40A O9A C37A C38A 20.5(6) . . . . ? C40B O9B C37B C38B -22(2) . . . . ? O9A C37A C38A C39A -36.9(6) . . . . ? O9B C37B C38B C39B 3(3) . . . . ? C37A C38A C39A C40A 39.0(7) . . . . ? C37B C38B C39B C40B 16(3) . . . . ? C37A O9A C40A C39A 5.0(7) . . . . ? C38A C39A C40A O9A -28.2(8) . . . . ? C37B O9B C40B C39B 32.0(18) . . . . ? C38B C39B C40B O9B -29(2) . . . . ? C44 O10 C41 C42 -48.2(15) . . . . ? O10 C41 C42 C43 27.6(19) . . . . ? C41 C42 C43 C44 -1(2) . . . . ? C41 O10 C44 C43 47.1(16) . . . . ? C42 C43 C44 O10 -26(2) . . . . ? 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 O1 H1 O4 0.84 1.99 2.753(4) 150.6 2_765 O3 H3 O2 0.84 1.82 2.632(3) 161.8 2_765 O5 H5 O6 0.84 1.78 2.612(3) 168.9 2_755 O7 H7 O9B 0.84 1.77 2.607(16) 170.4 1_645 O7 H7 O9A 0.84 1.81 2.603(5) 155.9 1_645 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 26.00 _diffrn_measured_fraction_theta_full 0.999 _refine_diff_density_max 1.408 _refine_diff_density_min -0.825 _refine_diff_density_rms 0.123