#------------------------------------------------------------------------------
#$Date: 2016-04-16 04:55:50 +0300 (Sat, 16 Apr 2016) $
#$Revision: 182158 $
#$URL: svn://www.crystallography.net/cod/cif/1/54/31/1543125.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_1543125
loop_
_publ_author_name
'Bai, Jun-Hua'
'Dong, Jin-Long'
_publ_section_title
;
 7-Hydroxy-4-(hydroxymethyl)coumarin
;
_journal_coeditor_code           SJ4022
_journal_issue                   4
_journal_name_full               IUCrData
_journal_page_first              x160598
_journal_paper_doi               10.1107/S2414314616005988
_journal_volume                  1
_journal_year                    2016
_chemical_formula_iupac          'C10 H8 O4'
_chemical_formula_moiety         'C10 H8 O4'
_chemical_formula_sum            'C10 H8 O4'
_chemical_formula_weight         192.16
_chemical_name_systematic
;
7-Hydroxy-4-(hydroxymethyl)-2-oxo-2H-chromene
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c 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            8
_cell_length_a                   13.217(10)
_cell_length_b                   9.831(7)
_cell_length_c                   13.627(9)
_cell_measurement_reflns_used    2954
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      26.5972
_cell_measurement_theta_min      2.9898
_cell_volume                     1771(2)
_computing_cell_refinement
;
SAINT (Bruker, 2007)
;
_computing_data_collection
;
SMART (Bruker, 2007)
;
_computing_data_reduction
;
SAINT (Bruker, 2007)
;
_computing_molecular_graphics
;
SHELXTL (Sheldrick, 2008)
;
_computing_publication_material
;
SHELXTL (Sheldrick, 2008)
;
_computing_structure_refinement
;
SHELXL97 (Sheldrick, 2008)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area-detector'
_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  0.0274
_diffrn_reflns_av_sigmaI/netI    0.0199
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            9109
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         2.99
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.113
_exptl_absorpt_correction_T_max  0.9669
_exptl_absorpt_correction_T_min  0.9637
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Sheldrick, 1996)
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.442
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.147
_refine_diff_density_min         -0.133
_refine_ls_extinction_coef       0.0102(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method
;
SHELXL97 (Sheldrick, 2008)
;
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     130
_refine_ls_number_reflns         1543
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.012
_refine_ls_R_factor_all          0.0435
_refine_ls_R_factor_gt           0.0333
_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)+(0.0246P)²+0.7759P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0714
_refine_ls_wR_factor_ref         0.0781
_reflns_number_gt                1273
_reflns_number_total             1543
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            sj4022sup1.cif
_cod_data_source_block           I
_cod_database_code               1543125
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, 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
O O1 0.37748(11) 0.30023(12) 0.36743(8) 0.0518(4) Uani d . 1 1
H H1 0.3289 0.2962 0.3301 0.078 Uiso calc R 1 1
O O2 0.50816(9) 0.10367(10) 0.65278(7) 0.0422(3) Uani d . 1 1
O O3 0.58112(10) 0.01787(12) 0.78346(8) 0.0520(4) Uani d . 1 1
O O4 0.27929(10) -0.28639(10) 0.74612(8) 0.0453(3) Uani d . 1 1
H H4 0.3219 -0.3459 0.7377 0.068 Uiso calc R 1 1
C C1 0.36957(14) 0.20140(15) 0.43601(11) 0.0400(4) Uani d . 1 1
C C2 0.29307(14) 0.10429(16) 0.43439(11) 0.0435(4) Uani d . 1 1
H H2 0.2454 0.1051 0.3842 0.052 Uiso calc R 1 1
C C3 0.28770(14) 0.00731(16) 0.50660(11) 0.0417(4) Uani d . 1 1
H H3 0.2360 -0.0568 0.5048 0.050 Uiso calc R 1 1
C C4 0.35857(13) 0.00311(14) 0.58290(10) 0.0348(4) Uani d . 1 1
C C5 0.43436(12) 0.10092(15) 0.58148(10) 0.0355(4) Uani d . 1 1
C C7 0.51031(14) 0.00963(16) 0.72671(11) 0.0406(4) Uani d . 1 1
C C8 0.43095(14) -0.08943(15) 0.72989(11) 0.0399(4) Uani d . 1 1
H H8 0.4299 -0.1520 0.7811 0.048 Uiso calc R 1 1
C C9 0.35823(13) -0.09497(14) 0.66163(10) 0.0357(4) Uani d . 1 1
C C10 0.27631(14) -0.20065(15) 0.66317(11) 0.0413(4) Uani d . 1 1
H H10A 0.2112 -0.1553 0.6612 0.050 Uiso calc R 1 1
H H10B 0.2820 -0.2561 0.6045 0.050 Uiso calc R 1 1
C C11 0.44128(14) 0.19958(15) 0.50994(11) 0.0407(4) Uani d . 1 1
H H11 0.4931 0.2636 0.5113 0.049 Uiso calc R 1 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
C1 O1 H1 109.5
C7 O2 C5 121.41(13)
C10 O4 H4 109.5
O1 C1 C11 117.37(15)
O1 C1 C2 122.58(15)
C11 C1 C2 120.05(15)
C3 C2 C1 120.22(15)
C3 C2 H2 119.9
C1 C2 H2 119.9
C2 C3 C4 121.23(16)
C2 C3 H3 119.4
C4 C3 H3 119.4
C5 C4 C3 116.87(14)
C5 C4 C9 118.39(14)
C3 C4 C9 124.74(15)
O2 C5 C11 115.99(14)
O2 C5 C4 120.98(13)
C11 C5 C4 123.03(15)
O3 C7 O2 116.05(15)
O3 C7 C8 126.12(15)
O2 C7 C8 117.83(14)
C9 C8 C7 122.18(15)
C9 C8 H8 118.9
C7 C8 H8 118.9
C8 C9 C4 119.16(15)
C8 C9 C10 122.45(14)
C4 C9 C10 118.38(14)
O4 C10 C9 113.87(14)
O4 C10 H10A 108.8
C9 C10 H10A 108.8
O4 C10 H10B 108.8
C9 C10 H10B 108.8
H10A C10 H10B 107.7
C5 C11 C1 118.60(15)
C5 C11 H11 120.7
C1 C11 H11 120.7
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C1 1.3521(18)
O1 H1 0.8200
O2 C7 1.3676(19)
O2 C5 1.377(2)
O3 C7 1.217(2)
O4 C10 1.4106(19)
O4 H4 0.8200
C1 C11 1.383(2)
C1 C2 1.391(3)
C2 C3 1.372(2)
C2 H2 0.9300
C3 C4 1.400(2)
C3 H3 0.9300
C4 C5 1.389(2)
C4 C9 1.442(2)
C5 C11 1.378(2)
C7 C8 1.432(3)
C8 C9 1.339(2)
C8 H8 0.9300
C9 C10 1.501(2)
C10 H10A 0.9700
C10 H10B 0.9700
C11 H11 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
O4 H4 O3 3_646 0.82 1.88 2.696(2) 179.2
O1 H1 O4 2_554 0.82 1.83 2.654(2) 179.6

_cod_database_fobs_code 1543125
