#------------------------------------------------------------------------------ #$Date: 2016-08-07 11:19:22 +0300 (Sun, 07 Aug 2016) $ #$Revision: 185212 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/22/51/7225197.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_7225197 loop_ _publ_author_name 'Veerakanellore, Giri Babu' 'Captain, Burjor' 'Ramamurthy, V.' _publ_section_title ; Solid-state photochemistry of cis-cinnamic acids: a competition between [2 + 2] addition and cis--trans isomerization ; _journal_issue 25 _journal_name_full CrystEngComm _journal_page_first 4708 _journal_paper_doi 10.1039/C6CE00682E _journal_volume 18 _journal_year 2016 _chemical_formula_sum 'C10 H9 Br O3' _chemical_formula_weight 257.08 _space_group_crystal_system monoclinic _space_group_IT_number 15 _space_group_name_Hall '-C 2yc' _space_group_name_H-M_alt 'C 1 2/c 1' _symmetry_space_group_name_Hall '-C 2yc' _symmetry_space_group_name_H-M 'C 1 2/c 1' _atom_sites_solution_hydrogens geom _audit_creation_method SHELXL-2014/7 _audit_update_record ; 2016-03-10 deposited with the CCDC. 2016-05-11 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90.8600(10) _cell_angle_gamma 90 _cell_formula_units_Z 8 _cell_length_a 18.770(2) _cell_length_b 4.7420(5) _cell_length_c 23.122(3) _cell_measurement_reflns_used 2682 _cell_measurement_temperature 296 _cell_measurement_theta_max 25.07 _cell_measurement_theta_min 2.78 _cell_volume 2057.8(4) _computing_cell_refinement 'SAINT+ V8.34A (Bruker, 2015)' _computing_data_collection 'APEX2 v2.2-0 (Bruker, 2007)' _computing_data_reduction 'SAINT+ V8.34A (Bruker, 2015)' _computing_molecular_graphics 'XSHELL v6.3.1 (Bruker, 2004)' _computing_publication_material 'XCIF v2014/2 (Bruker, 2014)' _computing_structure_refinement 'SHELXL-2014/7 (Sheldrick, 2014)' _computing_structure_solution 'SHELXS/SHELXTL V6.14 (Bruker, 2015)' _diffrn_ambient_temperature 296 _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_device_type 'Bruker SMART APEX2 CCD diffractometer' _diffrn_measurement_method 'omega scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0239 _diffrn_reflns_av_unetI/netI 0.0196 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 1.000 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_k_max 5 _diffrn_reflns_limit_k_min -5 _diffrn_reflns_limit_l_max 28 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_number 7936 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 1.000 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 25.498 _diffrn_reflns_theta_min 1.762 _exptl_absorpt_coefficient_mu 3.973 _exptl_absorpt_correction_T_max 0.7457 _exptl_absorpt_correction_T_min 0.5269 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS 2014/5 Bruker)' _exptl_crystal_colour Colourless _exptl_crystal_density_diffrn 1.660 _exptl_crystal_description Bar _exptl_crystal_F_000 1024 _exptl_crystal_size_max 0.300 _exptl_crystal_size_mid 0.100 _exptl_crystal_size_min 0.030 _refine_diff_density_max 1.025 _refine_diff_density_min -0.784 _refine_diff_density_rms 0.070 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.075 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 129 _refine_ls_number_reflns 1922 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.075 _refine_ls_R_factor_all 0.0550 _refine_ls_R_factor_gt 0.0443 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0430P)^2^+8.0294P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1043 _refine_ls_wR_factor_ref 0.1109 _reflns_Friedel_coverage 0.000 _reflns_number_gt 1593 _reflns_number_total 1922 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c6ce00682e2.cif _cod_data_source_block collect_0m _cod_depositor_comments ; The following automatic conversions were performed: '_exptl_absorpt_correction_type' value 'Multi-scan' changed to 'multi-scan' according to /usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26. Automatic conversion script Id: cif_fix_values 4268 2015-11-12 08:31:59Z antanas Adding full bibliography for 7225194--7225202.cif. ; _cod_original_cell_volume 2057.7(4) _cod_database_code 7225197 _shelx_shelxl_version_number 2014/7 _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _shelx_estimated_absorpt_t_min 0.382 _shelx_estimated_absorpt_t_max 0.890 _shelx_res_file ; collect_0m.res created by SHELXL-2014/7 TITL collect_0m in C2/c CELL 0.71073 18.7696 4.7420 23.1219 90.0000 90.860 90.0000 ZERR 8.00 0.0020 0.0005 0.0025 0.0000 0.001 0.0000 LATT 7 SYMM -X, Y, 0.5-Z SFAC C H O Br UNIT 80 72 24 8 OMIT -3 51 L.S. 8 ACTA BOND FMAP 2 PLAN 20 SIZE 0.03 0.10 0.30 TEMP 28.200 WGHT 0.043000 8.029400 FVAR 0.08233 MOLE 1 BR1 4 0.589658 1.127745 0.302420 11.00000 0.06567 0.10768 = 0.05966 -0.04024 0.00779 0.00299 O1 3 0.565445 0.225621 0.014408 11.00000 0.05628 0.06198 = 0.04361 -0.01306 0.01462 -0.01529 O2 3 0.466751 0.154279 0.064618 11.00000 0.05359 0.06095 = 0.05117 -0.01536 0.01286 -0.01805 AFIX 147 H3A 2 0.457513 0.049574 0.037295 11.00000 -1.50000 AFIX 0 O3 3 0.730466 0.913248 0.074531 11.00000 0.05096 0.09114 = 0.05103 -0.00442 0.01506 -0.01676 C1 1 0.637254 0.828843 0.138573 11.00000 0.03906 0.03586 = 0.04095 -0.00033 0.00041 0.00346 C2 1 0.604508 0.880864 0.191107 11.00000 0.03582 0.04538 = 0.04541 -0.00762 0.00265 0.00229 AFIX 43 H2A 2 0.563540 0.782026 0.200664 11.00000 -1.20000 AFIX 0 C3 1 0.632102 1.076446 0.228874 11.00000 0.04146 0.05479 = 0.04673 -0.01180 -0.00165 0.00895 C4 1 0.691906 1.227609 0.215366 11.00000 0.05043 0.04789 = 0.05880 -0.01083 -0.01282 0.00078 AFIX 43 H4 2 0.709403 1.363070 0.240962 11.00000 -1.20000 AFIX 0 C5 1 0.726008 1.179582 0.164193 11.00000 0.04029 0.05098 = 0.06091 0.00656 -0.00953 -0.00560 AFIX 43 H5 2 0.766670 1.281803 0.155254 11.00000 -1.20000 AFIX 0 C6 1 0.699768 0.978142 0.125725 11.00000 0.03706 0.04811 = 0.04466 0.00372 0.00005 0.00258 C7 1 0.609263 0.622240 0.097426 11.00000 0.04492 0.04185 = 0.03497 -0.00215 0.00770 0.00165 AFIX 43 H7 2 0.638252 0.578740 0.066402 11.00000 -1.20000 AFIX 0 C8 1 0.547505 0.490009 0.099195 11.00000 0.04781 0.04492 = 0.03681 -0.00665 0.00862 -0.00415 AFIX 43 H8 2 0.516200 0.531882 0.128787 11.00000 -1.20000 AFIX 0 C9 1 0.526964 0.279617 0.055935 11.00000 0.04477 0.03699 = 0.03691 0.00075 0.00161 -0.00120 C10 1 0.797061 1.042699 0.061393 11.00000 0.05891 0.15119 = 0.06660 0.00373 0.02066 -0.02928 AFIX 137 H10A 2 0.790450 1.242414 0.057141 11.00000 -1.50000 H10B 2 0.814781 0.965799 0.025996 11.00000 -1.50000 H10C 2 0.830682 1.006829 0.092217 11.00000 -1.50000 AFIX 0 HKLF 4 REM collect_0m in C2/c REM R1 = 0.0443 for 1593 Fo > 4sig(Fo) and 0.0550 for all 1922 data REM 129 parameters refined using 0 restraints END WGHT 0.0430 8.0307 REM Highest difference peak 1.025, deepest hole -0.784, 1-sigma level 0.070 Q1 1 0.5633 1.2574 0.2821 11.00000 0.05 1.03 Q2 1 0.6219 1.2685 0.2869 11.00000 0.05 0.69 Q3 1 0.6234 1.1132 0.2686 11.00000 0.05 0.30 Q4 1 0.7211 1.0183 0.1550 11.00000 0.05 0.23 Q5 1 0.6766 0.8371 0.1341 11.00000 0.05 0.22 Q6 1 0.5381 0.1949 -0.0095 11.00000 0.05 0.20 Q7 1 0.7989 1.3782 0.1303 11.00000 0.05 0.20 Q8 1 0.6209 0.7523 0.1210 11.00000 0.05 0.20 Q9 1 0.5525 0.1377 0.0385 11.00000 0.05 0.18 Q10 1 0.5271 0.4491 0.0739 11.00000 0.05 0.18 Q11 1 0.5818 0.4675 0.1108 11.00000 0.05 0.17 Q12 1 0.5986 0.1899 0.0277 11.00000 0.05 0.17 Q13 1 0.5638 0.6400 0.0921 11.00000 0.05 0.17 Q14 1 0.5350 0.9894 0.3286 11.00000 0.05 0.17 Q15 1 0.6375 0.7626 0.1688 11.00000 0.05 0.17 Q16 1 0.6752 1.0428 0.2275 11.00000 0.05 0.16 Q17 1 0.6454 0.9347 0.1239 11.00000 0.05 0.16 Q18 1 0.5636 0.0820 -0.0004 11.00000 0.05 0.16 Q19 1 0.8406 0.7980 0.0980 11.00000 0.05 0.15 Q20 1 0.6174 1.5147 0.3179 11.00000 0.05 0.15 ; _shelx_res_checksum 5072 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -y+1/2, z-1/2' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp Br1 Br 0.58966(3) 1.12775(14) 0.30242(2) 0.0776(2) Uani 1 1 d . . O1 O 0.56545(15) 0.2256(7) 0.01441(11) 0.0538(7) Uani 1 1 d . . O2 O 0.46675(15) 0.1543(7) 0.06462(12) 0.0551(7) Uani 1 1 d . . H3A H 0.4575 0.0496 0.0373 0.083 Uiso 1 1 calc R U O3 O 0.73047(15) 0.9132(8) 0.07453(13) 0.0642(9) Uani 1 1 d . . C1 C 0.63725(19) 0.8288(8) 0.13857(15) 0.0386(8) Uani 1 1 d . . C2 C 0.60451(19) 0.8809(8) 0.19111(16) 0.0422(8) Uani 1 1 d . . H2A H 0.5635 0.7820 0.2007 0.051 Uiso 1 1 calc R U C3 C 0.6321(2) 1.0764(9) 0.22887(17) 0.0477(10) Uani 1 1 d . . C4 C 0.6919(2) 1.2276(9) 0.21537(19) 0.0525(10) Uani 1 1 d . . H4 H 0.7094 1.3631 0.2410 0.063 Uiso 1 1 calc R U C5 C 0.7260(2) 1.1796(9) 0.16419(19) 0.0508(10) Uani 1 1 d . . H5 H 0.7667 1.2818 0.1553 0.061 Uiso 1 1 calc R U C6 C 0.69977(19) 0.9781(9) 0.12572(16) 0.0433(9) Uani 1 1 d . . C7 C 0.60926(19) 0.6222(8) 0.09743(15) 0.0405(8) Uani 1 1 d . . H7 H 0.6383 0.5787 0.0664 0.049 Uiso 1 1 calc R U C8 C 0.5475(2) 0.4900(8) 0.09920(15) 0.0431(9) Uani 1 1 d . . H8 H 0.5162 0.5319 0.1288 0.052 Uiso 1 1 calc R U C9 C 0.52696(19) 0.2796(8) 0.05593(15) 0.0395(8) Uani 1 1 d . . C10 C 0.7971(3) 1.0427(16) 0.0614(2) 0.092(2) Uani 1 1 d . . H10A H 0.7904 1.2424 0.0571 0.138 Uiso 1 1 calc R U H10B H 0.8148 0.9658 0.0260 0.138 Uiso 1 1 calc R U H10C H 0.8307 1.0068 0.0922 0.138 Uiso 1 1 calc R U 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 0.0657(3) 0.1077(5) 0.0597(3) -0.0402(3) 0.0078(2) 0.0030(3) O1 0.0563(16) 0.0620(18) 0.0436(15) -0.0131(14) 0.0146(13) -0.0153(15) O2 0.0536(16) 0.0609(19) 0.0512(16) -0.0154(14) 0.0129(13) -0.0180(14) O3 0.0510(16) 0.091(2) 0.0510(17) -0.0044(16) 0.0151(13) -0.0168(17) C1 0.0391(18) 0.0359(19) 0.0410(19) -0.0003(15) 0.0004(15) 0.0035(16) C2 0.0358(18) 0.045(2) 0.045(2) -0.0076(17) 0.0027(15) 0.0023(17) C3 0.041(2) 0.055(2) 0.047(2) -0.0118(18) -0.0017(16) 0.0090(18) C4 0.050(2) 0.048(2) 0.059(3) -0.011(2) -0.0128(19) 0.001(2) C5 0.040(2) 0.051(2) 0.061(2) 0.007(2) -0.0095(18) -0.0056(18) C6 0.0371(19) 0.048(2) 0.045(2) 0.0037(17) 0.0000(16) 0.0026(17) C7 0.045(2) 0.042(2) 0.0350(18) -0.0022(15) 0.0077(15) 0.0016(17) C8 0.048(2) 0.045(2) 0.0368(18) -0.0066(17) 0.0086(15) -0.0041(18) C9 0.045(2) 0.037(2) 0.0369(18) 0.0008(15) 0.0016(15) -0.0012(17) C10 0.059(3) 0.151(6) 0.067(3) 0.004(4) 0.021(2) -0.029(4) 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' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C6 O3 C10 118.1(4) C2 C1 C6 118.4(3) C2 C1 C7 121.9(3) C6 C1 C7 119.6(3) C3 C2 C1 120.6(4) C2 C3 C4 120.8(4) C2 C3 Br1 119.8(3) C4 C3 Br1 119.4(3) C3 C4 C5 120.2(4) C4 C5 C6 120.0(4) O3 C6 C5 124.2(4) O3 C6 C1 115.8(3) C5 C6 C1 120.0(4) C8 C7 C1 127.4(3) C7 C8 C9 121.8(3) O1 C9 O2 123.1(3) O1 C9 C8 121.5(3) O2 C9 C8 115.4(3) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance Br1 C3 1.904(4) O1 C9 1.237(4) O2 C9 1.295(4) O3 C6 1.360(5) O3 C10 1.429(5) C1 C2 1.392(5) C1 C6 1.406(5) C1 C7 1.458(5) C2 C3 1.370(5) C3 C4 1.372(6) C4 C5 1.373(6) C5 C6 1.390(6) C7 C8 1.319(5) C8 C9 1.460(5)