#------------------------------------------------------------------------------ #$Date: 2016-05-12 06:04:22 +0300 (Thu, 12 May 2016) $ #$Revision: 182890 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/22/51/7225195.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_7225195 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 'C11 H12 O4' _chemical_formula_weight 208.21 _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 79.8570(10) _cell_angle_beta 86.8460(10) _cell_angle_gamma 80.3430(10) _cell_formula_units_Z 2 _cell_length_a 3.9208(2) _cell_length_b 11.0581(7) _cell_length_c 12.1034(7) _cell_measurement_reflns_used 3574 _cell_measurement_temperature 296(2) _cell_measurement_theta_max 30.56 _cell_measurement_theta_min 2.33 _cell_volume 509.07(5) _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 0.999 _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 0.0158 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 0.999 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 6499 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 0.999 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 26.998 _diffrn_reflns_theta_min 1.710 _exptl_absorpt_coefficient_mu 0.104 _exptl_absorpt_correction_T_max 0.7461 _exptl_absorpt_correction_T_min 0.7073 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS 2014/5 Bruker)' _exptl_crystal_colour Colourless _exptl_crystal_density_diffrn 1.358 _exptl_crystal_description Bar _exptl_crystal_F_000 220 _exptl_crystal_size_max 0.380 _exptl_crystal_size_mid 0.280 _exptl_crystal_size_min 0.060 _refine_diff_density_max 0.253 _refine_diff_density_min -0.185 _refine_diff_density_rms 0.043 _refine_ls_extinction_coef 0.060(9) _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 1.046 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 140 _refine_ls_number_reflns 2193 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.046 _refine_ls_R_factor_all 0.0435 _refine_ls_R_factor_gt 0.0390 _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^)+(0.0525P)^2^+0.1134P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1037 _refine_ls_wR_factor_ref 0.1078 _reflns_Friedel_coverage 0.000 _reflns_number_gt 1930 _reflns_number_total 2193 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c6ce00682e2.cif _cod_data_source_block collect_0m_a _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 7225195 _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 0.962 _shelx_estimated_absorpt_t_max 0.994 _shelx_res_file ; collect_0m_a.res created by SHELXL-2014/7 TITL collect_0m_a.res in P-1 CELL 0.71073 3.9208 11.0581 12.1034 79.857 86.846 80.343 ZERR 2.000 0.0002 0.0007 0.0007 0.001 0.001 0.001 LATT 1 SFAC C H O UNIT 22 24 8 OMIT -3 54 L.S. 10 ACTA BOND $H FMAP 2 PLAN 20 SIZE 0.06 0.28 0.38 TEMP 23.000 WGHT 0.052500 0.113400 EXTI 0.059659 FVAR 1.49305 O1 3 0.268917 0.872190 1.074791 11.00000 0.13070 0.05359 = 0.04034 -0.02156 -0.02246 0.01570 AFIX 147 H1 2 0.162829 0.942967 1.073248 11.00000 -1.50000 AFIX 0 O2 3 0.075733 0.905427 0.901626 11.00000 0.09493 0.04836 = 0.03750 -0.01438 -0.01376 0.01190 O3 3 0.210319 0.492358 0.778426 11.00000 0.06529 0.03168 = 0.04501 -0.00771 -0.00113 -0.01360 O4 3 0.204179 0.763183 0.427244 11.00000 0.07153 0.04858 = 0.03443 -0.00834 -0.00754 -0.01334 C1 1 0.377398 0.687751 0.770650 11.00000 0.04115 0.03165 = 0.03462 -0.01031 -0.00049 -0.00263 C2 1 0.262672 0.601910 0.713224 11.00000 0.03856 0.02921 = 0.03910 -0.00958 0.00166 -0.00287 C3 1 0.208195 0.630246 0.599078 11.00000 0.04363 0.03518 = 0.04116 -0.01526 -0.00338 -0.00643 AFIX 43 H3 2 0.131803 0.573081 0.562289 11.00000 -1.20000 AFIX 0 C4 1 0.267995 0.744451 0.539514 11.00000 0.04096 0.03840 = 0.03309 -0.01030 -0.00128 -0.00184 C5 1 0.384719 0.829737 0.593442 11.00000 0.05145 0.03150 = 0.03775 -0.00682 0.00222 -0.00872 AFIX 43 H5 2 0.427272 0.905789 0.553362 11.00000 -1.20000 AFIX 0 C6 1 0.437116 0.800065 0.707946 11.00000 0.05010 0.03299 = 0.03827 -0.01295 -0.00016 -0.00925 AFIX 43 H6 2 0.515083 0.857535 0.743974 11.00000 -1.20000 AFIX 0 C7 1 0.464317 0.649176 0.888999 11.00000 0.05520 0.03121 = 0.03926 -0.00579 -0.00485 -0.00375 AFIX 43 H7 2 0.563430 0.566017 0.907956 11.00000 -1.20000 AFIX 0 C8 1 0.426786 0.712014 0.974645 11.00000 0.06505 0.03831 = 0.03388 -0.00451 -0.00946 -0.00513 AFIX 43 H8 2 0.530351 0.669795 1.040823 11.00000 -1.20000 AFIX 0 C9 1 0.245509 0.837976 0.978869 11.00000 0.06730 0.03988 = 0.03100 -0.00902 -0.00341 -0.00831 C10 1 0.103975 0.400595 0.724267 11.00000 0.06030 0.03483 = 0.06466 -0.01442 0.00105 -0.01540 AFIX 137 H10A 2 -0.112989 0.433765 0.688891 11.00000 -1.50000 H10B 2 0.077872 0.328248 0.778912 11.00000 -1.50000 H10C 2 0.275556 0.378089 0.668593 11.00000 -1.50000 AFIX 0 C11 1 0.288263 0.873426 0.359430 11.00000 0.07659 0.05434 = 0.03575 -0.00233 -0.00412 -0.00926 AFIX 137 H11A 2 0.153017 0.944813 0.384395 11.00000 -1.50000 H11B 2 0.238754 0.873666 0.282584 11.00000 -1.50000 H11C 2 0.529798 0.876240 0.365519 11.00000 -1.50000 AFIX 0 HKLF 4 REM collect_0m_a.res in P-1 REM R1 = 0.0390 for 1930 Fo > 4sig(Fo) and 0.0435 for all 2193 data REM 140 parameters refined using 0 restraints END WGHT 0.0525 0.1133 REM Highest difference peak 0.253, deepest hole -0.185, 1-sigma level 0.043 Q1 1 0.2881 0.9242 0.9095 11.00000 0.05 0.25 Q2 1 0.3592 0.6787 0.8341 11.00000 0.05 0.17 Q3 1 0.3677 0.6367 0.7440 11.00000 0.05 0.17 Q4 1 0.0606 0.8636 0.9364 11.00000 0.05 0.16 Q5 1 0.3634 0.7816 0.9654 11.00000 0.05 0.16 Q6 1 0.3383 0.6023 0.6557 11.00000 0.05 0.15 Q7 1 0.3873 0.6705 1.0629 11.00000 0.05 0.15 Q8 1 0.2988 0.8282 0.6586 11.00000 0.05 0.15 Q9 1 0.0878 0.8393 1.0607 11.00000 0.05 0.14 Q10 1 0.1321 0.6370 0.6607 11.00000 0.05 0.14 Q11 1 0.3893 0.7769 0.5667 11.00000 0.05 0.14 Q12 1 0.2284 0.8044 0.5739 11.00000 0.05 0.14 Q13 1 0.3015 0.6750 0.9330 11.00000 0.05 0.14 Q14 1 0.2858 0.7506 0.7523 11.00000 0.05 0.13 Q15 1 -0.0659 0.9629 0.9147 11.00000 0.05 0.13 Q16 1 0.0629 0.8932 0.8693 11.00000 0.05 0.13 Q17 1 -0.0031 0.9828 0.9058 11.00000 0.05 0.13 Q18 1 0.3434 0.9002 1.0262 11.00000 0.05 0.12 Q19 1 0.4755 0.7052 0.9197 11.00000 0.05 0.11 Q20 1 0.4606 0.8239 1.1073 11.00000 0.05 0.11 ; _shelx_res_checksum 6181 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 0.2689(4) 0.87219(10) 1.07479(9) 0.0760(4) Uani 1 1 d . . H1 H 0.1628 0.9430 1.0732 0.114 Uiso 1 1 calc R U O2 O 0.0757(3) 0.90543(9) 0.90163(8) 0.0617(3) Uani 1 1 d . . O3 O 0.2103(3) 0.49236(8) 0.77843(8) 0.0465(3) Uani 1 1 d . . O4 O 0.2042(3) 0.76318(9) 0.42724(7) 0.0507(3) Uani 1 1 d . . C1 C 0.3774(3) 0.68775(10) 0.77065(10) 0.0356(3) Uani 1 1 d . . C2 C 0.2627(3) 0.60191(10) 0.71322(10) 0.0356(3) Uani 1 1 d . . C3 C 0.2082(3) 0.63025(11) 0.59908(10) 0.0388(3) Uani 1 1 d . . H3 H 0.1318 0.5731 0.5623 0.047 Uiso 1 1 calc R U C4 C 0.2680(3) 0.74445(11) 0.53951(10) 0.0375(3) Uani 1 1 d . . C5 C 0.3847(3) 0.82974(11) 0.59344(10) 0.0400(3) Uani 1 1 d . . H5 H 0.4273 0.9058 0.5534 0.048 Uiso 1 1 calc R U C6 C 0.4371(3) 0.80007(11) 0.70795(10) 0.0393(3) Uani 1 1 d . . H6 H 0.5151 0.8575 0.7440 0.047 Uiso 1 1 calc R U C7 C 0.4643(3) 0.64918(11) 0.88900(10) 0.0421(3) Uani 1 1 d . . H7 H 0.5634 0.5660 0.9080 0.051 Uiso 1 1 calc R U C8 C 0.4268(4) 0.71201(12) 0.97464(10) 0.0460(3) Uani 1 1 d . . H8 H 0.5304 0.6698 1.0408 0.055 Uiso 1 1 calc R U C9 C 0.2455(4) 0.83798(12) 0.97887(10) 0.0456(3) Uani 1 1 d . . C10 C 0.1040(4) 0.40060(12) 0.72427(13) 0.0517(4) Uani 1 1 d . . H10A H -0.1130 0.4338 0.6889 0.078 Uiso 1 1 calc R U H10B H 0.0779 0.3282 0.7789 0.078 Uiso 1 1 calc R U H10C H 0.2756 0.3781 0.6686 0.078 Uiso 1 1 calc R U C11 C 0.2883(4) 0.87343(14) 0.35943(12) 0.0563(4) Uani 1 1 d . . H11A H 0.1530 0.9448 0.3844 0.084 Uiso 1 1 calc R U H11B H 0.2388 0.8737 0.2826 0.084 Uiso 1 1 calc R U H11C H 0.5298 0.8762 0.3655 0.084 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 0.1307(11) 0.0536(7) 0.0403(6) -0.0216(5) -0.0225(6) 0.0157(7) O2 0.0949(8) 0.0484(6) 0.0375(5) -0.0144(4) -0.0138(5) 0.0119(5) O3 0.0653(6) 0.0317(5) 0.0450(5) -0.0077(4) -0.0011(4) -0.0136(4) O4 0.0715(6) 0.0486(5) 0.0344(5) -0.0083(4) -0.0075(4) -0.0133(5) C1 0.0411(6) 0.0316(6) 0.0346(6) -0.0103(4) -0.0005(5) -0.0026(4) C2 0.0386(6) 0.0292(5) 0.0391(6) -0.0096(4) 0.0017(5) -0.0029(4) C3 0.0436(6) 0.0352(6) 0.0412(6) -0.0153(5) -0.0034(5) -0.0064(5) C4 0.0410(6) 0.0384(6) 0.0331(6) -0.0103(5) -0.0013(5) -0.0018(5) C5 0.0514(7) 0.0315(6) 0.0378(6) -0.0068(5) 0.0022(5) -0.0087(5) C6 0.0501(7) 0.0330(6) 0.0383(6) -0.0129(5) -0.0002(5) -0.0092(5) C7 0.0552(7) 0.0312(6) 0.0393(6) -0.0058(5) -0.0048(5) -0.0037(5) C8 0.0650(8) 0.0383(7) 0.0339(6) -0.0045(5) -0.0095(5) -0.0051(6) C9 0.0673(8) 0.0399(7) 0.0310(6) -0.0090(5) -0.0034(5) -0.0083(6) C10 0.0603(8) 0.0348(6) 0.0647(9) -0.0144(6) 0.0010(7) -0.0154(6) C11 0.0766(10) 0.0543(8) 0.0357(7) -0.0023(6) -0.0041(6) -0.0093(7) 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 C9 O1 H1 109.5 C2 O3 C10 117.69(10) C4 O4 C11 117.91(10) C6 C1 C2 117.47(11) C6 C1 C7 123.16(11) C2 C1 C7 118.99(10) O3 C2 C3 123.80(10) O3 C2 C1 115.26(10) C3 C2 C1 120.95(11) C2 C3 C4 119.74(11) C2 C3 H3 120.1 C4 C3 H3 120.1 O4 C4 C5 124.53(11) O4 C4 C3 114.94(10) C5 C4 C3 120.53(11) C6 C5 C4 119.03(11) C6 C5 H5 120.5 C4 C5 H5 120.5 C5 C6 C1 122.28(11) C5 C6 H6 118.9 C1 C6 H6 118.9 C8 C7 C1 131.50(11) C8 C7 H7 114.2 C1 C7 H7 114.2 C7 C8 C9 129.00(12) C7 C8 H8 115.5 C9 C8 H8 115.5 O2 C9 O1 122.13(12) O2 C9 C8 124.80(11) O1 C9 C8 113.02(11) O3 C10 H10A 109.5 O3 C10 H10B 109.5 H10A C10 H10B 109.5 O3 C10 H10C 109.5 H10A C10 H10C 109.5 H10B C10 H10C 109.5 O4 C11 H11A 109.5 O4 C11 H11B 109.5 H11A C11 H11B 109.5 O4 C11 H11C 109.5 H11A C11 H11C 109.5 H11B C11 H11C 109.5 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance O1 C9 1.2952(15) O1 H1 0.8200 O2 C9 1.2368(16) O3 C2 1.3643(14) O3 C10 1.4281(15) O4 C4 1.3685(14) O4 C11 1.4217(17) C1 C6 1.3854(16) C1 C2 1.4130(16) C1 C7 1.4628(16) C2 C3 1.3821(17) C3 C4 1.3891(17) C3 H3 0.9300 C4 C5 1.3854(17) C5 C6 1.3853(17) C5 H5 0.9300 C6 H6 0.9300 C7 C8 1.3348(17) C7 H7 0.9300 C8 C9 1.4618(18) C8 H8 0.9300 C10 H10A 0.9600 C10 H10B 0.9600 C10 H10C 0.9600 C11 H11A 0.9600 C11 H11B 0.9600 C11 H11C 0.9600