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#$Date: 2022-07-01 10:17:37 +0300 (Fri, 01 Jul 2022) $
#$Revision: 276475 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/56/8105604.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_8105604
loop_
_publ_author_name
'Wang, Bei-Bei'
'Zang, Chuan-Yi'
'Zhang, Ling'
'Wu, Wei-Na'
_publ_section_title
;
 Crystal structure of 3-methyl-2-oxo-2H-chromen-7-yl propionate, C13H12O4
;
_journal_issue                   2
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              243
_journal_page_last               244
_journal_paper_doi               10.1515/ncrs-2018-0281
_journal_volume                  234
_journal_year                    2019
_chemical_formula_sum            'C13 H12 O4'
_chemical_formula_weight         232.23
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2017/1
_cell_angle_alpha                79.257(12)
_cell_angle_beta                 76.820(12)
_cell_angle_gamma                74.687(11)
_cell_formula_units_Z            2
_cell_length_a                   6.141(5)
_cell_length_b                   8.108(6)
_cell_length_c                   12.234(9)
_cell_measurement_reflns_used    1273
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      21.33
_cell_measurement_theta_min      2.18
_cell_volume                     566.9(8)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0106
_diffrn_reflns_av_unetI/netI     0.0190
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            2893
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        24.997
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_min         1.725
_exptl_absorpt_coefficient_mu    0.101
_exptl_absorpt_correction_T_max  0.991
_exptl_absorpt_correction_T_min  0.981
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_description       rod
_exptl_crystal_F_000             244
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.080
_refine_diff_density_max         0.364
_refine_diff_density_min         -0.298
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         1990
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.088
_refine_ls_R_factor_all          0.0627
_refine_ls_R_factor_gt           0.0515
_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/[σ²(Fo²)+(0.0728P)²+0.1974P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1469
_refine_ls_wR_factor_ref         0.1575
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1556
_reflns_number_total             1990
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2018-0281_suppl.cif
_cod_data_source_block           1
_cod_original_cell_volume        566.8(7)
_cod_database_code               8105604
_shelx_shelxl_version_number     2017/1
_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   0.980
_shelx_estimated_absorpt_t_max   0.992
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
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.2510(3) 0.0298(2) 0.85649(15) 0.0751(6) Uani 1 1 d . . . . .
O2 O 0.0494(3) -0.12022(19) 0.79958(13) 0.0610(5) Uani 1 1 d . . . . .
O3 O 0.4041(3) 0.3615(3) 0.29128(15) 0.0809(6) Uani 1 1 d . . . . .
O4 O 0.2805(2) 0.22045(19) 0.45430(12) 0.0540(4) Uani 1 1 d . . . . .
C1 C 0.4215(6) -0.2544(4) 1.0112(3) 0.0959(10) Uani 1 1 d . . . . .
H1A H 0.444679 -0.357035 1.065020 0.144 Uiso 1 1 calc R U . . .
H1B H 0.561221 -0.251871 0.956954 0.144 Uiso 1 1 calc R U . . .
H1C H 0.379030 -0.154790 1.050098 0.144 Uiso 1 1 calc R U . . .
C2 C 0.2340(5) -0.2536(3) 0.9515(2) 0.0722(7) Uani 1 1 d . . . . .
H2A H 0.276733 -0.356084 0.913999 0.087 Uiso 1 1 calc R U . . .
H2B H 0.094638 -0.259054 1.007094 0.087 Uiso 1 1 calc R U . . .
C3 C 0.1860(4) -0.0993(3) 0.86638(18) 0.0553(6) Uani 1 1 d . . . . .
C4 C -0.0021(4) 0.0090(3) 0.71067(17) 0.0496(5) Uani 1 1 d . . . . .
C5 C -0.2322(4) 0.0800(3) 0.70763(19) 0.0565(6) Uani 1 1 d . . . . .
H5A H -0.345748 0.047562 0.766009 0.068 Uiso 1 1 calc R U . . .
C6 C -0.2902(4) 0.1988(3) 0.6171(2) 0.0567(6) Uani 1 1 d . . . . .
H6A H -0.444486 0.246220 0.614149 0.068 Uiso 1 1 calc R U . . .
C7 C -0.1222(3) 0.2496(2) 0.52984(17) 0.0459(5) Uani 1 1 d . . . . .
C8 C 0.1062(3) 0.1751(2) 0.53752(16) 0.0442(5) Uani 1 1 d . . . . .
C9 C 0.1691(4) 0.0535(3) 0.62614(17) 0.0490(5) Uani 1 1 d . . . . .
H9A H 0.322999 0.003177 0.628561 0.059 Uiso 1 1 calc R U . . .
C10 C -0.1680(4) 0.3680(3) 0.43092(19) 0.0523(5) Uani 1 1 d . . . . .
H10A H -0.319884 0.416951 0.423622 0.063 Uiso 1 1 calc R U . . .
C11 C 0.0003(4) 0.4105(3) 0.34860(18) 0.0510(5) Uani 1 1 d . . . . .
C12 C 0.2373(4) 0.3343(3) 0.35891(18) 0.0543(5) Uani 1 1 d . . . . .
C13 C -0.0395(5) 0.5291(3) 0.2426(2) 0.0692(7) Uani 1 1 d . . . . .
H13A H 0.105616 0.540856 0.195891 0.104 Uiso 1 1 calc R U . . .
H13B H -0.121520 0.482765 0.202191 0.104 Uiso 1 1 calc R U . . .
H13C H -0.128268 0.640215 0.261331 0.104 Uiso 1 1 calc R U . . .
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
C3 O2 C4 118.47(17) . .
C8 O4 C12 121.92(17) . .
C2 C1 H1A 109.5 . .
C2 C1 H1B 109.5 . .
H1A C1 H1B 109.5 . .
C2 C1 H1C 109.5 . .
H1A C1 H1C 109.5 . .
H1B C1 H1C 109.5 . .
C3 C2 C1 113.3(2) . .
C3 C2 H2A 108.9 . .
C1 C2 H2A 108.9 . .
C3 C2 H2B 108.9 . .
C1 C2 H2B 108.9 . .
H2A C2 H2B 107.7 . .
O1 C3 O2 122.6(2) . .
O1 C3 C2 126.5(2) . .
O2 C3 C2 110.9(2) . .
C9 C4 C5 122.0(2) . .
C9 C4 O2 120.6(2) . .
C5 C4 O2 117.19(19) . .
C6 C5 C4 119.0(2) . .
C6 C5 H5A 120.5 . .
C4 C5 H5A 120.5 . .
C5 C6 C7 121.1(2) . .
C5 C6 H6A 119.4 . .
C7 C6 H6A 119.4 . .
C6 C7 C8 117.5(2) . .
C6 C7 C10 124.6(2) . .
C8 C7 C10 117.82(19) . .
C9 C8 O4 117.02(18) . .
C9 C8 C7 122.57(19) . .
O4 C8 C7 120.41(18) . .
C4 C9 C8 117.8(2) . .
C4 C9 H9A 121.1 . .
C8 C9 H9A 121.1 . .
C11 C10 C7 122.1(2) . .
C11 C10 H10A 118.9 . .
C7 C10 H10A 118.9 . .
C10 C11 C12 119.4(2) . .
C10 C11 C13 123.9(2) . .
C12 C11 C13 116.7(2) . .
O3 C12 O4 115.7(2) . .
O3 C12 C11 126.0(2) . .
O4 C12 C11 118.29(19) . .
C11 C13 H13A 109.5 . .
C11 C13 H13B 109.5 . .
H13A C13 H13B 109.5 . .
C11 C13 H13C 109.5 . .
H13A C13 H13C 109.5 . .
H13B C13 H13C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C3 1.192(3) .
O2 C3 1.356(3) .
O2 C4 1.392(3) .
O3 C12 1.203(3) .
O4 C8 1.374(2) .
O4 C12 1.377(3) .
C1 C2 1.496(4) .
C1 H1A 0.9600 .
C1 H1B 0.9600 .
C1 H1C 0.9600 .
C2 C3 1.482(3) .
C2 H2A 0.9700 .
C2 H2B 0.9700 .
C4 C9 1.368(3) .
C4 C5 1.384(3) .
C5 C6 1.372(3) .
C5 H5A 0.9300 .
C6 C7 1.390(3) .
C6 H6A 0.9300 .
C7 C8 1.390(3) .
C7 C10 1.430(3) .
C8 C9 1.374(3) .
C9 H9A 0.9300 .
C10 C11 1.336(3) .
C10 H10A 0.9300 .
C11 C12 1.447(3) .
C11 C13 1.491(3) .
C13 H13A 0.9600 .
C13 H13B 0.9600 .
C13 H13C 0.9600 .
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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
C4 O2 C3 O1 5.0(3) . . . .
C4 O2 C3 C2 -176.41(19) . . . .
C1 C2 C3 O1 -13.6(4) . . . .
C1 C2 C3 O2 167.9(2) . . . .
C3 O2 C4 C9 60.3(3) . . . .
C3 O2 C4 C5 -124.4(2) . . . .
C9 C4 C5 C6 -0.1(3) . . . .
O2 C4 C5 C6 -175.41(18) . . . .
C4 C5 C6 C7 -0.6(3) . . . .
C5 C6 C7 C8 0.2(3) . . . .
C5 C6 C7 C10 177.74(19) . . . .
C12 O4 C8 C9 176.66(18) . . . .
C12 O4 C8 C7 -2.8(3) . . . .
C6 C7 C8 C9 0.9(3) . . . .
C10 C7 C8 C9 -176.73(17) . . . .
C6 C7 C8 O4 -179.66(17) . . . .
C10 C7 C8 O4 2.7(3) . . . .
C5 C4 C9 C8 1.3(3) . . . .
O2 C4 C9 C8 176.37(17) . . . .
O4 C8 C9 C4 178.91(17) . . . .
C7 C8 C9 C4 -1.7(3) . . . .
C6 C7 C10 C11 -178.96(19) . . . .
C8 C7 C10 C11 -1.5(3) . . . .
C7 C10 C11 C12 0.3(3) . . . .
C7 C10 C11 C13 178.13(19) . . . .
C8 O4 C12 O3 -178.77(19) . . . .
C8 O4 C12 C11 1.5(3) . . . .
C10 C11 C12 O3 -180.0(2) . . . .
C13 C11 C12 O3 2.0(3) . . . .
C10 C11 C12 O4 -0.3(3) . . . .
C13 C11 C12 O4 -178.26(18) . . . .
