#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/83/2238300.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_2238300
loop_
_publ_author_name
'Bibila Mayaya Bisseyou, Yvon'
'Abou, Akoun'
'Djandé, Abdoulaye'
'Danger, Grégoire'
'Kakou-Yao, Rita'
_publ_section_title
;
 2-Oxo-2H-chromen-4-yl propionate
;
_journal_coeditor_code           ZQ2203
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1125
_journal_page_last               o1126
_journal_paper_doi               10.1107/S1600536813016358
_journal_volume                  69
_journal_year                    2013
_chemical_formula_iupac          'C12 H10 O4'
_chemical_formula_moiety         'C12 H10 O4'
_chemical_formula_sum            'C12 H10 O4'
_chemical_formula_weight         218.20
_chemical_melting_point_gt       358
_chemical_melting_point_lt       359
_chemical_name_systematic
;
2-Oxo-2H-chromen-4-yl propionic acid
;
_space_group_IT_number           62
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2n'
_symmetry_space_group_name_H-M   'P n m a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.2834(3)
_cell_length_b                   6.7081(2)
_cell_length_c                   16.8068(6)
_cell_measurement_reflns_used    8092
_cell_measurement_temperature    298
_cell_measurement_theta_max      28.96
_cell_measurement_theta_min      3.27
_cell_volume                     1046.63(6)
_computing_cell_refinement       'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_data_collection       'COLLECT (Hooft, 1998)'
_computing_data_reduction        'DENZO/SCALEPACK (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material
'publCIF (Westrip, 2010) and WinGX (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SIR2004 (Burla et al., 2005)'
_diffrn_ambient_temperature      298
_diffrn_measured_fraction_theta_full 0.974
_diffrn_measured_fraction_theta_max 0.952
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'φ and ω scans'
_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  0.037
_diffrn_reflns_av_sigmaI/netI    0.0273
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            8092
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         28.96
_diffrn_reflns_theta_min         3.27
_exptl_absorpt_coefficient_mu    0.105
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.385
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       parallelepiped
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.238
_refine_diff_density_min         -0.156
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    88
_refine_ls_number_parameters     98
_refine_ls_number_reflns         1431
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.0718
_refine_ls_R_factor_gt           0.0561
_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/[σ²(Fo²)+(0.0589P)²+0.3235P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1333
_refine_ls_wR_factor_ref         0.1459
_reflns_number_gt                1155
_reflns_number_total             1431
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            zq2203.cif
_cod_data_source_block           I
_cod_database_code               2238300
_cod_database_fobs_code          2238300
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z+1/2'
'-x, y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z-1/2'
'x, -y-1/2, z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_disorder_assembly
_atom_site_disorder_group
O O3 0.06438(15) 0.2500 0.59531(8) 0.0595(5) Uani d S 1 2 A 1
O O1 -0.01804(18) 0.2500 0.35401(8) 0.0607(5) Uani d S 1 2 A 1
C C4 0.1469(2) 0.2500 0.46462(11) 0.0434(4) Uani d S 1 2 A 1
C C3 0.0233(2) 0.2500 0.51696(10) 0.0428(4) Uani d S 1 2 A 1
C C2 -0.1113(2) 0.2500 0.48839(12) 0.0481(5) Uani d S 1 2 A 1
H H2 -0.1890 0.2500 0.5233 0.058 Uiso calc SR 1 2 A 1
C C10 -0.0290(2) 0.2500 0.65979(11) 0.0460(5) Uani d S 1 2 A 1
C C5 0.1204(2) 0.2500 0.38352(12) 0.0461(5) Uani d S 1 2 A 1
O O4 -0.15508(17) 0.2500 0.65323(9) 0.0695(5) Uani d S 1 2 A 1
C C11 0.0580(2) 0.2500 0.73405(11) 0.0616(7) Uani d S 1 2 A 1
H H11A 0.1197 0.3668 0.7343 0.074 Uiso calc PR 0.50 1 A 1
H H11B 0.1197 0.1332 0.7343 0.074 Uiso calc PR 0.50 1 A 1
C C9 0.2892(2) 0.2500 0.49029(13) 0.0633(7) Uani d S 1 2 A 1
H H9 0.3096 0.2500 0.5445 0.076 Uiso calc SR 1 2 A 1
O O2 -0.25262(19) 0.2500 0.37225(11) 0.0921(8) Uani d S 1 2 A 1
C C1 -0.1362(2) 0.2500 0.40383(13) 0.0579(6) Uani d S 1 2 A 1
C C8 0.4004(3) 0.2500 0.43576(16) 0.0765(9) Uani d S 1 2 A 1
H H8 0.4954 0.2500 0.4532 0.092 Uiso calc SR 1 2 A 1
C C12 -0.0325(3) 0.2500 0.80905(13) 0.0723(8) Uani d S 1 2 A 1
H H12A -0.0996 0.1412 0.8072 0.108 Uiso calc PR 0.50 1 A 1
H H12B -0.0842 0.3735 0.8129 0.108 Uiso calc PR 0.50 1 A 1
H H12C 0.0290 0.2352 0.8546 0.108 Uiso calc PR 0.50 1 A 1
C C6 0.2310(3) 0.2500 0.32839(13) 0.0603(6) Uani d S 1 2 A 1
H H6 0.2111 0.2500 0.2742 0.072 Uiso calc SR 1 2 A 1
C C7 0.3703(3) 0.2500 0.35516(15) 0.0687(7) Uani d S 1 2 A 1
H H7 0.4457 0.2500 0.3187 0.082 Uiso calc SR 1 2 A 1
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
C3 O3 C10 125.20(15)
C5 O1 C1 121.52(16)
C5 C4 C9 118.32(18)
C5 C4 C3 117.24(17)
C9 C4 C3 124.44(18)
C2 C3 O3 127.17(17)
C2 C3 C4 121.50(17)
O3 C3 C4 111.33(16)
C3 C2 C1 120.26(18)
C3 C2 H2 119.9
C1 C2 H2 119.9
O4 C10 O3 123.27(18)
O4 C10 C11 128.30(18)
O3 C10 C11 108.43(16)
O1 C5 C6 116.82(19)
O1 C5 C4 121.34(18)
C6 C5 C4 121.8(2)
C10 C11 C12 113.39(19)
C10 C11 H11A 108.9
C12 C11 H11A 108.9
C10 C11 H11B 108.9
C12 C11 H11B 108.9
H11A C11 H11B 107.7
C8 C9 C4 120.3(2)
C8 C9 H9 119.9
C4 C9 H9 119.9
O2 C1 O1 116.48(19)
O2 C1 C2 125.4(2)
O1 C1 C2 118.13(18)
C9 C8 C7 120.0(2)
C9 C8 H8 120.0
C7 C8 H8 120.0
C7 C6 C5 118.8(2)
C7 C6 H6 120.6
C5 C6 H6 120.6
C6 C7 C8 120.8(2)
C6 C7 H7 119.6
C8 C7 H7 119.6
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O3 C3 1.371(2)
O3 C10 1.388(2)
O1 C5 1.378(3)
O1 C1 1.380(3)
C4 C5 1.385(3)
C4 C9 1.390(3)
C4 C3 1.446(3)
C3 C2 1.339(3)
C2 C1 1.440(3)
C2 H2 0.9300
C10 O4 1.176(3)
C10 C11 1.487(3)
C5 C6 1.383(3)
C11 C12 1.515(3)
C11 H11A 0.9700
C11 H11B 0.9700
C9 C8 1.380(3)
C9 H9 0.9300
O2 C1 1.204(3)
C8 C7 1.383(4)
C8 H8 0.9300
C12 H12A 0.9600
C12 H12B 0.9600
C12 H12C 0.9600
C6 C7 1.370(4)
C6 H6 0.9300
C7 H7 0.9300
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C2 H2 O4 . 0.93 2.21 2.800(3) 120.9
C6 H6 O2 6_656 0.93 2.48 3.376(3) 160.8
C8 H8 O2 1_655 0.93 2.71 3.394(3) 131.4
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
C10 O3 C3 C2 0.0
C10 O3 C3 C4 180.0
C5 C4 C3 C2 0.0
C9 C4 C3 C2 180.0
C5 C4 C3 O3 180.0
C9 C4 C3 O3 0.0
O3 C3 C2 C1 180.0
C4 C3 C2 C1 0.0
C3 O3 C10 O4 0.0
C3 O3 C10 C11 180.0
C1 O1 C5 C6 180.0
C1 O1 C5 C4 0.0
C9 C4 C5 O1 180.0
C3 C4 C5 O1 0.0
C9 C4 C5 C6 0.0
C3 C4 C5 C6 180.0
O4 C10 C11 C12 0.0
O3 C10 C11 C12 180.0
C5 C4 C9 C8 0.0
C3 C4 C9 C8 180.0
C5 O1 C1 O2 180.0
C5 O1 C1 C2 0.0
C3 C2 C1 O2 180.0
C3 C2 C1 O1 0.0
C4 C9 C8 C7 0.0
O1 C5 C6 C7 180.0
C4 C5 C6 C7 0.0
C5 C6 C7 C8 0.0
C9 C8 C7 C6 0.0
