#------------------------------------------------------------------------------ #$Date: 2016-05-12 06:04:22 +0300 (Thu, 12 May 2016) $ #$Revision: 182890 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/22/51/7225199.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_7225199 loop_ _publ_author_name 'Veerakanellore, Giri Babu' 'Captain, Burjor' 'Ramamurthy, Vaidhyanathan' _publ_section_title ; Solid-state photochemistry of cis-cinnamic acids: A competition between [2+2] addition and cis-trans isomerization ; _journal_name_full CrystEngComm _journal_paper_doi 10.1039/C6CE00682E _journal_year 2016 _chemical_formula_sum 'C12 H12 O3' _chemical_formula_weight 204.22 _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -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 71.8220(10) _cell_angle_beta 84.9210(10) _cell_angle_gamma 64.4150(10) _cell_formula_units_Z 2 _cell_length_a 7.7380(6) _cell_length_b 8.1099(6) _cell_length_c 10.0048(8) _cell_measurement_reflns_used 2286 _cell_measurement_temperature 296(2) _cell_measurement_theta_max 27.90 _cell_measurement_theta_min 2.92 _cell_volume 537.24(7) _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(2) _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 0.0190 _diffrn_reflns_av_unetI/netI 0.0163 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 1.000 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 11 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_number 5904 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 1.000 _diffrn_reflns_theta_full 24.999 _diffrn_reflns_theta_max 24.999 _diffrn_reflns_theta_min 2.146 _exptl_absorpt_coefficient_mu 0.090 _exptl_absorpt_correction_T_max 0.7461 _exptl_absorpt_correction_T_min 0.6867 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS 2014/5 Bruker)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.262 _exptl_crystal_description plate _exptl_crystal_F_000 216 _exptl_crystal_size_max 0.500 _exptl_crystal_size_mid 0.320 _exptl_crystal_size_min 0.060 _refine_diff_density_max 0.369 _refine_diff_density_min -0.293 _refine_diff_density_rms 0.050 _refine_ls_extinction_coef 0.072(15) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method 'SHELXL-2014/7 (Sheldrick 2014' _refine_ls_goodness_of_fit_ref 1.062 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 138 _refine_ls_number_reflns 1889 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.062 _refine_ls_R_factor_all 0.0719 _refine_ls_R_factor_gt 0.0617 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0857P)^2^+0.1812P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1697 _refine_ls_wR_factor_ref 0.1813 _reflns_Friedel_coverage 0.000 _reflns_number_gt 1521 _reflns_number_total 1889 _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 ; _cod_database_code 7225199 _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 0.956 _shelx_estimated_absorpt_t_max 0.995 _shelx_res_file ; collect_0m.res created by SHELXL-2014/7 TITL collect_0m in P-1 CELL 0.71073 7.7380 8.1099 10.0048 71.822 84.921 64.415 ZERR 2.00 0.0006 0.0006 0.0008 0.001 0.001 0.001 LATT 1 SFAC C H O UNIT 24 24 6 OMIT -3 50 L.S. 4 ACTA BOND FMAP 2 PLAN 20 SIZE 0.06 0.32 0.50 TEMP 23.000 WGHT 0.085700 0.181200 EXTI 0.071539 FVAR 0.36111 MOLE 1 O1 3 -0.320189 0.990624 0.094383 11.00000 0.07546 0.07891 = 0.09901 -0.04665 -0.01245 -0.02946 O2 3 -0.307719 0.799587 -0.028481 11.00000 0.07747 0.09523 = 0.09808 -0.05131 -0.01610 -0.03504 AFIX 147 H2 2 -0.422852 0.870593 -0.040443 11.00000 -1.50000 AFIX 0 O3 3 0.254229 0.877868 0.320310 11.00000 0.05730 0.08502 = 0.11682 -0.05982 -0.01196 -0.02219 C1 1 0.280789 0.657388 0.205155 11.00000 0.06332 0.05951 = 0.06343 -0.02173 -0.00076 -0.02834 C2 1 0.394368 0.492154 0.167380 11.00000 0.08186 0.06673 = 0.07761 -0.03120 -0.00283 -0.02946 AFIX 43 H2A 2 0.338499 0.450765 0.113848 11.00000 -1.20000 AFIX 0 C3 1 0.585262 0.389621 0.206873 11.00000 0.07820 0.06954 = 0.09712 -0.03752 -0.00164 -0.01561 AFIX 43 H3 2 0.657900 0.280196 0.180216 11.00000 -1.20000 AFIX 0 C4 1 0.668641 0.448817 0.285686 11.00000 0.06419 0.08201 = 0.10259 -0.03380 -0.00902 -0.01255 AFIX 43 H4 2 0.798466 0.378693 0.312841 11.00000 -1.20000 AFIX 0 C5 1 0.563378 0.610736 0.325529 11.00000 0.06308 0.08333 = 0.09083 -0.03639 -0.01039 -0.02416 AFIX 43 H5 2 0.621946 0.649737 0.379072 11.00000 -1.20000 AFIX 0 C6 1 0.368972 0.716006 0.285468 11.00000 0.05917 0.06308 = 0.07032 -0.02729 -0.00148 -0.02449 C7 1 0.077184 0.767882 0.162502 11.00000 0.06605 0.06153 = 0.06806 -0.02554 -0.00319 -0.02885 AFIX 43 H7 2 0.012353 0.876937 0.191091 11.00000 -1.20000 AFIX 0 C8 1 -0.024877 0.729505 0.087595 11.00000 0.07209 0.06915 = 0.08220 -0.03534 -0.00686 -0.03064 AFIX 43 H8 2 0.035988 0.621434 0.057384 11.00000 -1.20000 AFIX 0 C9 1 -0.228974 0.849230 0.050144 11.00000 0.07392 0.06951 = 0.07009 -0.02710 -0.00640 -0.03748 C10 1 0.341669 0.950504 0.394722 11.00000 0.06289 0.08752 = 0.10109 -0.04889 -0.01132 -0.02955 AFIX 23 H10A 2 0.442036 0.977047 0.340478 11.00000 -1.20000 H10B 2 0.398564 0.856155 0.484827 11.00000 -1.20000 AFIX 0 C11 1 0.195558 1.124066 0.415988 11.00000 0.07689 0.17554 = 0.32324 -0.19425 -0.05454 -0.00062 AFIX 43 H11 2 0.107969 1.186119 0.338777 11.00000 -1.20000 AFIX 0 C12 1 0.147905 1.210979 0.487852 11.00000 0.08057 0.19105 = 0.19560 -0.14381 -0.01379 -0.02969 AFIX 93 H12A 2 0.218667 1.170824 0.571601 11.00000 -1.20000 H12B 2 0.036595 1.325091 0.465253 11.00000 -1.20000 AFIX 0 HKLF 4 REM collect_0m in P-1 REM R1 = 0.0617 for 1521 Fo > 4sig(Fo) and 0.0719 for all 1889 data REM 138 parameters refined using 0 restraints END WGHT 0.0857 0.1813 REM Highest difference peak 0.369, deepest hole -0.293, 1-sigma level 0.050 Q1 1 0.2057 1.1522 0.3832 11.00000 0.05 0.37 Q2 1 0.1321 1.0765 0.4984 11.00000 0.05 0.32 Q3 1 0.0623 1.0387 0.5256 11.00000 0.05 0.19 Q4 1 0.2128 1.0433 0.6204 11.00000 0.05 0.19 Q5 1 0.2259 1.2811 0.3866 11.00000 0.05 0.18 Q6 1 0.1292 1.2790 0.2701 11.00000 0.05 0.17 Q7 1 0.0414 1.3171 0.5386 11.00000 0.05 0.16 Q8 1 0.3520 0.6245 0.1417 11.00000 0.05 0.13 Q9 1 -0.3415 0.8985 0.1442 11.00000 0.05 0.12 Q10 1 -0.1029 0.8356 0.0229 11.00000 0.05 0.11 Q11 1 -0.4410 1.0688 0.0620 11.00000 0.05 0.10 Q12 1 0.4754 0.7136 0.2406 11.00000 0.05 0.10 Q13 1 -0.2908 0.9999 0.0222 11.00000 0.05 0.10 Q14 1 0.2703 1.0340 0.1718 11.00000 0.05 0.09 Q15 1 -0.2888 0.9375 -0.1458 11.00000 0.05 0.09 Q16 1 0.8406 0.4533 0.2556 11.00000 0.05 0.09 Q17 1 0.5201 0.4818 0.1338 11.00000 0.05 0.09 Q18 1 0.0301 0.7142 -0.0157 11.00000 0.05 0.09 Q19 1 0.3076 0.6234 0.3044 11.00000 0.05 0.09 Q20 1 -0.4432 0.9850 0.1273 11.00000 0.05 0.08 ; _shelx_res_checksum 23204 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, -z' 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 O1 O -0.3202(2) 0.9906(2) 0.09438(19) 0.0796(6) Uani 1 1 d . . O2 O -0.3077(3) 0.7996(3) -0.0285(2) 0.0839(6) Uani 1 1 d . . H2 H -0.4229 0.8706 -0.0404 0.126 Uiso 1 1 calc R U O3 O 0.2542(2) 0.8779(2) 0.3203(2) 0.0809(6) Uani 1 1 d . . C1 C 0.2808(3) 0.6574(3) 0.2052(2) 0.0602(6) Uani 1 1 d . . C2 C 0.3944(4) 0.4922(3) 0.1674(3) 0.0734(7) Uani 1 1 d . . H2A H 0.3385 0.4508 0.1138 0.088 Uiso 1 1 calc R U C3 C 0.5853(4) 0.3896(4) 0.2069(3) 0.0840(8) Uani 1 1 d . . H3 H 0.6579 0.2802 0.1802 0.101 Uiso 1 1 calc R U C4 C 0.6686(4) 0.4488(4) 0.2857(3) 0.0875(8) Uani 1 1 d . . H4 H 0.7985 0.3787 0.3128 0.105 Uiso 1 1 calc R U C5 C 0.5634(4) 0.6107(4) 0.3255(3) 0.0782(7) Uani 1 1 d . . H5 H 0.6219 0.6497 0.3791 0.094 Uiso 1 1 calc R U C6 C 0.3690(3) 0.7160(3) 0.2855(2) 0.0627(6) Uani 1 1 d . . C7 C 0.0772(3) 0.7679(3) 0.1625(2) 0.0627(6) Uani 1 1 d . . H7 H 0.0124 0.8769 0.1911 0.075 Uiso 1 1 calc R U C8 C -0.0249(4) 0.7295(3) 0.0876(3) 0.0704(7) Uani 1 1 d . . H8 H 0.0360 0.6214 0.0574 0.084 Uiso 1 1 calc R U C9 C -0.2290(4) 0.8492(3) 0.0501(2) 0.0664(6) Uani 1 1 d . . C10 C 0.3417(3) 0.9505(4) 0.3947(3) 0.0786(7) Uani 1 1 d . . H10A H 0.4420 0.9770 0.3405 0.094 Uiso 1 1 calc R U H10B H 0.3986 0.8562 0.4848 0.094 Uiso 1 1 calc R U C11 C 0.1956(5) 1.1241(7) 0.4160(7) 0.177(3) Uani 1 1 d . . H11 H 0.1080 1.1861 0.3388 0.212 Uiso 1 1 calc R U C12 C 0.1479(5) 1.2110(7) 0.4879(5) 0.1431(18) Uani 1 1 d . . H12A H 0.2187 1.1708 0.5716 0.172 Uiso 1 1 calc R U H12B H 0.0366 1.3251 0.4653 0.172 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 O1 0.0755(11) 0.0789(11) 0.0990(13) -0.0467(10) -0.0124(9) -0.0295(9) O2 0.0775(11) 0.0952(13) 0.0981(13) -0.0513(11) -0.0161(10) -0.0350(10) O3 0.0573(9) 0.0850(11) 0.1168(14) -0.0598(10) -0.0120(9) -0.0222(8) C1 0.0633(13) 0.0595(12) 0.0634(12) -0.0217(10) -0.0008(10) -0.0283(10) C2 0.0819(16) 0.0667(14) 0.0776(15) -0.0312(12) -0.0028(12) -0.0295(12) C3 0.0782(17) 0.0695(15) 0.0971(19) -0.0375(14) -0.0016(14) -0.0156(13) C4 0.0642(15) 0.0820(17) 0.103(2) -0.0338(15) -0.0090(14) -0.0125(13) C5 0.0631(14) 0.0833(16) 0.0908(17) -0.0364(14) -0.0104(12) -0.0242(12) C6 0.0592(12) 0.0631(13) 0.0703(13) -0.0273(10) -0.0015(10) -0.0245(10) C7 0.0661(13) 0.0615(12) 0.0681(13) -0.0255(10) -0.0032(10) -0.0288(11) C8 0.0721(15) 0.0692(14) 0.0822(15) -0.0353(12) -0.0069(12) -0.0306(12) C9 0.0739(14) 0.0695(14) 0.0701(14) -0.0271(11) -0.0064(11) -0.0375(12) C10 0.0629(14) 0.0875(17) 0.1011(18) -0.0489(15) -0.0113(12) -0.0296(12) C11 0.077(2) 0.176(4) 0.323(6) -0.194(5) -0.055(3) -0.001(2) C12 0.081(2) 0.191(4) 0.196(4) -0.144(4) -0.014(2) -0.030(2) 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' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C6 O3 C10 118.05(18) C2 C1 C6 117.7(2) C2 C1 C7 122.0(2) C6 C1 C7 120.3(2) C3 C2 C1 121.8(2) C4 C3 C2 119.6(2) C3 C4 C5 120.9(2) C4 C5 C6 119.8(2) O3 C6 C5 123.6(2) O3 C6 C1 116.2(2) C5 C6 C1 120.1(2) C8 C7 C1 126.9(2) C7 C8 C9 122.9(2) O1 C9 O2 122.8(2) O1 C9 C8 121.12(19) O2 C9 C8 116.1(2) O3 C10 C11 108.3(2) C12 C11 C10 144.2(5) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance O1 C9 1.254(3) O2 C9 1.283(2) O3 C6 1.363(3) O3 C10 1.437(3) C1 C2 1.397(3) C1 C6 1.397(3) C1 C7 1.459(3) C2 C3 1.366(4) C3 C4 1.365(4) C4 C5 1.376(4) C5 C6 1.392(3) C7 C8 1.321(3) C8 C9 1.460(3) C10 C11 1.440(4) C11 C12 1.093(5)