#------------------------------------------------------------------------------ #$Date: 2017-10-14 22:27:35 +0300 (Sat, 14 Oct 2017) $ #$Revision: 202017 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/20/17/7201786.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_7201786 loop_ _publ_author_name 'Mahon, Mary F.' 'Raithby, Paul R.' 'Sparkes, Hazel A.' _publ_section_title ; Investigation of the factors favouring solid state [2 + 2] cycloaddition reactions; the [2 + 2] cycloaddition reaction of coumarin-3-carboxylic acid ; _journal_issue 5 _journal_name_full CrystEngComm _journal_page_first 573 _journal_paper_doi 10.1039/b715941b _journal_volume 10 _journal_year 2008 _chemical_formula_moiety 'C10 H6 O4' _chemical_formula_sum 'C10 H6 O4' _chemical_formula_weight 190.15 _chemical_name_systematic ; ? ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 107.108(3) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 11.2410(7) _cell_length_b 5.4821(4) _cell_length_c 13.7463(12) _cell_measurement_reflns_used 3490 _cell_measurement_temperature 150(2) _cell_measurement_theta_max 26.373 _cell_measurement_theta_min 2.91 _cell_volume 809.62(11) _computing_cell_refinement 'HKL Scalepack (Otwinowski & Minor 1997)' _computing_data_collection 'Collect (Nonius BV, 1997-2000)' _computing_data_reduction 'HKL Denzo and Scalepack (Otwinowski & Minor 1997)' _computing_molecular_graphics 'POV-Ray (Cason, 1991)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'SIR92 (Altomare, 1993)' _diffrn_ambient_temperature 150(2) _diffrn_measured_fraction_theta_full 0.980 _diffrn_measured_fraction_theta_max 0.979 _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method 'Nonius KappaCCD' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0531 _diffrn_reflns_av_sigmaI/netI 0.0750 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_number 4016 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 26.37 _diffrn_reflns_theta_min 3.79 _exptl_absorpt_coefficient_mu 0.123 _exptl_absorpt_correction_T_max 0.966 _exptl_absorpt_correction_T_min 0.899 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'Sortav (Blessing 1995)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.560 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 392 _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.35 _exptl_crystal_size_min 0.30 _refine_diff_density_max 0.270 _refine_diff_density_min -0.245 _refine_diff_density_rms 0.079 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.024 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 128 _refine_ls_number_reflns 1617 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.024 _refine_ls_R_factor_all 0.0967 _refine_ls_R_factor_gt 0.0494 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0598P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1058 _refine_ls_wR_factor_ref 0.1230 _reflns_number_gt 1014 _reflns_number_total 1617 _reflns_threshold_expression >2sigma(I) _cod_data_source_file b715941b.txt _cod_data_source_block e:\hazel\papers\coumar~1\k03has1\k03has1 _cod_original_sg_symbol_H-M 'P 21/n' _cod_database_code 7201786 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' 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 O1 O 0.60016(13) 0.1982(2) 0.24595(10) 0.0259(4) Uani 1 1 d . . . O2 O 0.72692(13) 0.3045(2) 0.15852(11) 0.0327(4) Uani 1 1 d . . . O3 O 0.76158(15) 0.0284(2) 0.01586(11) 0.0401(5) Uani 1 1 d . . . H3A H 0.7677 0.1473 0.0556 0.048 Uiso 1 1 calc R . . O4 O 0.64418(14) -0.2987(2) -0.02817(11) 0.0357(4) Uani 1 1 d . . . C1 C 0.51892(18) 0.0352(3) 0.26944(15) 0.0235(5) Uani 1 1 d . . . C2 C 0.47625(19) 0.0911(4) 0.35118(15) 0.0286(5) Uani 1 1 d . . . H2 H 0.5026 0.2358 0.3895 0.034 Uiso 1 1 calc R . . C3 C 0.39463(19) -0.0676(4) 0.37584(16) 0.0307(5) Uani 1 1 d . . . H3 H 0.3648 -0.0323 0.4322 0.037 Uiso 1 1 calc R . . C4 C 0.35518(19) -0.2790(4) 0.31937(16) 0.0299(5) Uani 1 1 d . . . H4 H 0.2983 -0.3860 0.3369 0.036 Uiso 1 1 calc R . . C5 C 0.39849(19) -0.3329(3) 0.23844(16) 0.0282(5) Uani 1 1 d . . . H5 H 0.3713 -0.4772 0.2001 0.034 Uiso 1 1 calc R . . C6 C 0.48279(18) -0.1763(3) 0.21179(15) 0.0236(5) Uani 1 1 d . . . C7 C 0.53472(19) -0.2236(3) 0.13073(16) 0.0249(5) Uani 1 1 d . . . H7 H 0.5103 -0.3657 0.0902 0.030 Uiso 1 1 calc R . . C8 C 0.61795(18) -0.0692(3) 0.11079(14) 0.0224(5) Uani 1 1 d . . . C9 C 0.65342(19) 0.1510(3) 0.17089(15) 0.0251(5) Uani 1 1 d . . . C10 C 0.6747(2) -0.1248(4) 0.02752(16) 0.0280(5) 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 O1 0.0266(8) 0.0241(7) 0.0280(8) -0.0028(6) 0.0095(7) -0.0002(6) O2 0.0317(9) 0.0305(8) 0.0358(9) -0.0007(6) 0.0099(8) -0.0062(7) O3 0.0449(10) 0.0447(10) 0.0384(10) -0.0088(7) 0.0241(8) -0.0128(8) O4 0.0416(10) 0.0374(8) 0.0319(9) -0.0087(7) 0.0165(8) -0.0041(7) C1 0.0207(11) 0.0238(10) 0.0253(12) 0.0032(8) 0.0055(10) 0.0014(9) C2 0.0291(13) 0.0304(11) 0.0246(12) -0.0033(9) 0.0054(10) 0.0050(10) C3 0.0280(13) 0.0393(12) 0.0259(12) 0.0028(10) 0.0095(10) 0.0067(10) C4 0.0242(12) 0.0361(12) 0.0311(13) 0.0054(10) 0.0107(10) 0.0018(9) C5 0.0244(12) 0.0277(10) 0.0309(13) 0.0004(9) 0.0056(10) 0.0003(9) C6 0.0205(11) 0.0245(10) 0.0248(12) 0.0011(8) 0.0052(9) 0.0031(9) C7 0.0250(12) 0.0238(10) 0.0239(12) -0.0010(8) 0.0042(9) 0.0037(9) C8 0.0211(11) 0.0243(10) 0.0215(11) 0.0011(8) 0.0057(9) 0.0026(9) C9 0.0238(12) 0.0269(11) 0.0224(12) 0.0033(8) 0.0035(10) 0.0008(9) C10 0.0261(12) 0.0300(11) 0.0273(12) 0.0028(10) 0.0070(10) -0.0003(10) 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 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C9 O1 C1 121.46(15) . . ? C10 O3 H3A 109.5 . . ? C2 C1 O1 117.27(17) . . ? C2 C1 C6 122.30(18) . . ? O1 C1 C6 120.43(17) . . ? C3 C2 C1 118.45(18) . . ? C3 C2 H2 120.8 . . ? C1 C2 H2 120.8 . . ? C2 C3 C4 120.96(18) . . ? C2 C3 H3 119.5 . . ? C4 C3 H3 119.5 . . ? C5 C4 C3 120.03(19) . . ? C5 C4 H4 120.0 . . ? C3 C4 H4 120.0 . . ? C4 C5 C6 120.50(19) . . ? C4 C5 H5 119.7 . . ? C6 C5 H5 119.7 . . ? C1 C6 C5 117.74(19) . . ? C1 C6 C7 118.51(17) . . ? C5 C6 C7 123.73(18) . . ? C8 C7 C6 120.87(18) . . ? C8 C7 H7 119.6 . . ? C6 C7 H7 119.6 . . ? C7 C8 C9 119.82(18) . . ? C7 C8 C10 120.36(17) . . ? C9 C8 C10 119.81(16) . . ? O2 C9 O1 116.05(17) . . ? O2 C9 C8 125.15(18) . . ? O1 C9 C8 118.78(16) . . ? O4 C10 O3 120.17(18) . . ? O4 C10 C8 122.68(18) . . ? O3 C10 C8 117.14(17) . . ? 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 O1 C9 1.361(2) . ? O1 C1 1.382(2) . ? O2 C9 1.226(2) . ? O3 C10 1.333(2) . ? O3 H3A 0.8400 . ? O4 C10 1.208(2) . ? C1 C2 1.380(3) . ? C1 C6 1.395(3) . ? C2 C3 1.377(3) . ? C2 H2 0.9500 . ? C3 C4 1.393(3) . ? C3 H3 0.9500 . ? C4 C5 1.371(3) . ? C4 H4 0.9500 . ? C5 C6 1.405(3) . ? C5 H5 0.9500 . ? C6 C7 1.426(3) . ? C7 C8 1.348(3) . ? C7 H7 0.9500 . ? C8 C9 1.451(3) . ? C8 C10 1.496(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 O3 H3A O2 0.84 1.83 2.5955(18) 151.4 . loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 10298