#------------------------------------------------------------------------------
#$Date: 2017-10-13 08:28:26 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201972 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/10/43/2104349.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2104349
loop_
_publ_author_name
'Howard, Judith A. K.'
'Mahon, Mary F.'
'Raithby, Paul R.'
'Sparkes, Hazel A.'
_publ_section_title
;
 Trans-cinnamic acid and coumarin-3-carboxylic acid:
 experimental charge-density studies to shed light on [2+2]
 cycloaddition reactions
;
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section B'
_journal_page_first              230
_journal_page_last               237
_journal_paper_doi               10.1107/S0108768109001566
_journal_volume                  65
_journal_year                    2009
_chemical_formula_moiety         'C10 H6 O4'
_chemical_formula_sum            'C10 H6 O4'
_chemical_formula_weight         190.15
_chemical_name_common            'coumarin-3-carboxylic acid'
_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_type_scat_source
'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 107.2560(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   11.19920(10)
_cell_length_b                   5.46620(10)
_cell_length_c                   13.7267(2)
_cell_measurement_reflns_used    66859
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      67.355
_cell_measurement_theta_min      3.098
_cell_volume                     802.49(2)
_computing_cell_refinement
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.5 (release 18-04-2008 CrysAlis171 .NET)
(compiled Apr 18 2008,18:17:43)
;
_computing_data_collection
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.5 (release 18-04-2008 CrysAlis171 .NET)
(compiled Apr 18 2008,18:17:43)
;
_computing_data_reduction
;
CrysAlisPro, Oxford Diffraction Ltd.,
Version 1.171.33.5 (release 18-04-2008 CrysAlis171 .NET)
(compiled Apr 18 2008,18:17:43)
;
_computing_molecular_graphics    'Volkov et al, (2006)'
_computing_publication_material  'Volkov et al, (2006)'
_computing_structure_refinement  'Volkov et al, (2006)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1998)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 10.3317
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type
'Goniometer Xcalibur, detector: Atlas (Gemini ultra Mo)'
_diffrn_measurement_method       CCD
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0226
_diffrn_reflns_av_sigmaI/netI    0.0529
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            147662
_diffrn_reflns_theta_full        57.79
_diffrn_reflns_theta_max         57.79
_diffrn_reflns_theta_min         3.098
_exptl_absorpt_coefficient_mu    0.124
_exptl_absorpt_correction_T_max  0.965
_exptl_absorpt_correction_T_min  0.891
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlis RED, Oxford Diffraction Ltd.,
Version 1.171.33.18 (release 23-07-2008 CrysAlis171 .NET)
(compiled Jul 23 2008,18:57:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.574
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             392
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.52
_exptl_crystal_size_min          0.29
_refine_diff_density_max         0.151
_refine_diff_density_min         -0.138
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.669
_refine_ls_matrix_type           full
_refine_ls_number_parameters     367
_refine_ls_number_reflns         8933
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.028
_refine_ls_R_factor_gt           0.016
_refine_ls_shift/su_max          0
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details
;
calc w1 = 1/[s²(Fo)]
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.014
_reflns_number_gt                8933
_reflns_number_total             11309
_reflns_threshold_expression     'I >3 σ(I)'
_cod_data_source_file            so5021.cif
_cod_data_source_block           2a
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2104349
_cod_database_fobs_code          2104349
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_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_occupancy
O(1) 0.900004(14) 0.19923(2) 0.254215(12) 0.012 1
O(2) 0.772812(16) 0.30671(3) 0.341479(13) 0.015 1
O(3) 0.73811(2) 0.03092(4) 0.483840(17) 0.021 1
O(4) 0.856569(19) -0.29867(3) 0.528735(15) 0.018 1
C(1) 0.980824(12) 0.03660(2) 0.230834(10) 0.011 1
C(2) 1.023635(14) 0.09363(2) 0.148238(12) 0.014 1
C(3) 1.106404(15) -0.06761(3) 0.123505(12) 0.015 1
C(4) 1.146074(15) -0.28187(3) 0.180257(13) 0.015 1
C(5) 1.102190(13) -0.33595(2) 0.262115(12) 0.013 1
C(6) 1.017881(12) -0.17668(2) 0.288303(10) 0.01 1
C(7) 0.965884(12) -0.22503(2) 0.369680(10) 0.011 1
C(8) 0.881696(12) -0.06819(2) 0.389306(10) 0.01 1
C(9) 0.846586(12) 0.15328(2) 0.328619(10) 0.011 1
C(10) 0.825109(14) -0.12314(2) 0.472765(11) 0.013 1
H(3A) 0.730201 0.162694 0.430715 0.028 1
H(2) 0.993041 0.256504 0.103211 0.031 1
H(3) 1.140067 -0.023708 0.059563 0.034 1
H(4) 1.209662 -0.408184 0.160928 0.034 1
H(5) 1.130951 -0.500765 0.306234 0.03 1
H(7) 0.9972 -0.384099 0.41704 0.027 1
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_2
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C(1) O(1) C(9) . . . 121.770(10) yes
C(10) O(3) H(3A) . . . 106.22 no
O(1) C(1) C(2) . . . 117.130(10) yes
O(1) C(1) C(6) . . . 120.890(10) yes
C(2) C(1) C(6) . . . 121.990(10) yes
C(1) C(2) C(3) . . . 118.180(10) yes
C(1) C(2) H(2) . . . 121.58 no
C(3) C(2) H(2) . . . 120.23 no
C(2) C(3) C(4) . . . 121.120(10) yes
C(2) C(3) H(3) . . . 118.41 no
C(4) C(3) H(3) . . . 120.47 no
C(3) C(4) C(5) . . . 119.880(10) yes
C(3) C(4) H(4) . . . 121.35 no
C(5) C(4) H(4) . . . 118.77 no
C(4) C(5) C(6) . . . 120.100(10) yes
C(4) C(5) H(5) . . . 120.95 no
C(6) C(5) H(5) . . . 118.94 no
C(1) C(6) C(5) . . . 118.720(10) yes
C(1) C(6) C(7) . . . 118.230(10) yes
C(5) C(6) C(7) . . . 123.030(10) yes
C(6) C(7) C(8) . . . 120.380(10) yes
C(6) C(7) H(7) . . . 118.98 no
C(8) C(7) H(7) . . . 120.60 no
C(7) C(8) C(9) . . . 119.770(10) yes
C(7) C(8) C(10) . . . 120.120(10) yes
C(9) C(8) C(10) . . . 120.110(10) yes
O(1) C(9) O(2) . . . 116.730(10) yes
O(1) C(9) C(8) . . . 118.810(10) yes
O(2) C(9) C(8) . . . 124.440(10) yes
O(3) C(10) O(4) . . . 120.85(2) yes
O(3) C(10) C(8) . . . 116.850(10) yes
O(4) C(10) C(8) . . . 122.290(10) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O(1) C(1) . . 1.3729(2) yes
O(1) C(9) . . 1.3515(2) yes
O(2) C(9) . . 1.2263(2) yes
O(3) C(10) . . 1.3302(2) yes
O(3) H(3A) . . 1.0100 no
O(4) C(10) . . 1.2142(2) yes
C(1) C(2) . . 1.3910(2) yes
C(1) C(6) . . 1.3998(2) yes
C(2) C(3) . . 1.3921(2) yes
C(2) H(2) . . 1.0800 no
C(3) C(4) . . 1.4038(2) yes
C(3) H(3) . . 1.0800 no
C(4) C(5) . . 1.3853(2) yes
C(4) H(4) . . 1.0800 no
C(5) C(6) . . 1.4071(2) yes
C(5) H(5) . . 1.0800 no
C(6) C(7) . . 1.4292(2) yes
C(7) C(8) . . 1.3591(2) yes
C(7) H(7) . . 1.0800 no
C(8) C(9) . . 1.4559(2) yes
C(8) C(10) . . 1.4950(2) yes
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C(1) O(1) C(9) O(2) . . . . -177.83(2) yes
C(9) O(1) C(1) C(2) . . . . 175.56(2) yes
C(9) O(1) C(1) C(6) . . . . -4.490(10) yes
C(1) O(1) C(9) C(8) . . . . 3.660(10) yes
H(3A) O(2) C(9) O(1) . . . . 176.76 yes
C(9) O(2) H(3A) O(3) . . . . 12.53 yes
H(3A) O(2) C(9) C(8) . . . . -4.82 yes
C(10) O(3) H(3A) O(2) . . . . -8.67 yes
H(3A) O(3) C(10) O(4) . . . . 178.28 yes
H(3A) O(3) C(10) C(8) . . . . -1.35 yes
O(1) C(1) C(2) C(3) . . . . 179.54(2) yes
O(1) C(1) C(2) H(2) . . . . -1.43 yes
O(1) C(1) C(6) C(5) . . . . -179.16(2) yes
O(1) C(1) C(6) C(7) . . . . 2.200(10) yes
C(6) C(1) C(2) C(3) . . . . -0.420(10) yes
C(2) C(1) C(6) C(5) . . . . 0.790(10) yes
C(2) C(1) C(6) C(7) . . . . -177.84(2) yes
C(6) C(1) C(2) H(2) . . . . 178.62 yes
C(1) C(2) C(3) C(4) . . . . -0.140(10) yes
C(1) C(2) C(3) H(3) . . . . -179.82 yes
H(2) C(2) C(3) C(4) . . . . -179.18 yes
H(2) C(2) C(3) H(3) . . . . 1.13 yes
C(2) C(3) C(4) C(5) . . . . 0.300(10) yes
C(2) C(3) C(4) H(4) . . . . 179.48 yes
H(3) C(3) C(4) C(5) . . . . 179.98 yes
H(3) C(3) C(4) H(4) . . . . -0.84 yes
C(3) C(4) C(5) C(6) . . . . 0.080(10) yes
C(3) C(4) C(5) H(5) . . . . 179.41 yes
H(4) C(4) C(5) C(6) . . . . -179.11 yes
H(4) C(4) C(5) H(5) . . . . 0.22 yes
C(4) C(5) C(6) C(1) . . . . -0.610(10) yes
C(4) C(5) C(6) C(7) . . . . 177.96(2) yes
H(5) C(5) C(6) C(1) . . . . -179.95 yes
H(5) C(5) C(6) C(7) . . . . -1.39 yes
C(1) C(6) C(7) C(8) . . . . 0.730(10) yes
C(1) C(6) C(7) H(7) . . . . -176.92 yes
C(5) C(6) C(7) C(8) . . . . -177.84(2) yes
C(5) C(6) C(7) H(7) . . . . 4.51 yes
C(6) C(7) C(8) C(9) . . . . -1.470(10) yes
C(6) C(7) C(8) C(10) . . . . 178.39(2) yes
H(7) C(7) C(8) C(9) . . . . 176.14 yes
H(7) C(7) C(8) C(10) . . . . -4.00 yes
C(7) C(8) C(9) O(1) . . . . -0.670(10) yes
C(7) C(8) C(9) O(2) . . . . -179.05(2) yes
C(7) C(8) C(10) O(3) . . . . -176.21(2) yes
C(7) C(8) C(10) O(4) . . . . 4.16(2) yes
C(10) C(8) C(9) O(1) . . . . 179.47(2) yes
C(10) C(8) C(9) O(2) . . . . 1.090(10) yes
C(9) C(8) C(10) O(3) . . . . 3.65(2) yes
C(9) C(8) C(10) O(4) . . . . -175.98(2) yes
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 10298
