#------------------------------------------------------------------------------
#$Date: 2023-01-21 10:43:35 +0200 (Sat, 21 Jan 2023) $
#$Revision: 280495 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/65/8106522.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_8106522
loop_
_publ_author_name
'Lou, Benyong'
'Zhang, Mei'
'Huang, Yali'
'Wu, Huazhong'
_publ_section_title
;
 Crystal structure of
 7-hydroxy-3-(4-hydroxyphenyl)-4H-1-benzopyran-4-one-N,N-dimethylformamide
 (1/1), C18H17NO5
;
_journal_issue                   2
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              321
_journal_page_last               322
_journal_paper_doi               10.1515/ncrs-2016-0260
_journal_volume                  232
_journal_year                    2017
_chemical_formula_moiety         'C15 H10 O4, C3 H7 N O'
_chemical_formula_sum            'C18 H17 N O5'
_chemical_formula_weight         327.33
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 97.146(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.260(4)
_cell_length_b                   20.454(12)
_cell_length_c                   12.386(8)
_cell_measurement_reflns_used    3627
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      27.5283
_cell_measurement_theta_min      2.5893
_cell_volume                     1573.6(17)
_computing_cell_refinement       'CrystalClear '
_computing_data_collection       'CrystalClear (Rigaku, 2000)'
_computing_data_reduction        'CrystalClear '
_computing_molecular_graphics    'X-Seed (Barbour, 2001)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 14.6306
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       CCD_Profile_fitting
_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  0.0235
_diffrn_reflns_av_sigmaI/netI    0.0249
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            12072
_diffrn_reflns_theta_full        27.52
_diffrn_reflns_theta_max         27.52
_diffrn_reflns_theta_min         2.59
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.9254
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.175
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         3557
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.0666
_refine_ls_R_factor_gt           0.0497
_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)+(0.0498P)²+0.3782P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1111
_refine_ls_wR_factor_ref         0.1214
_reflns_number_gt                2778
_reflns_number_total             3557
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            suppl_ncrs-2016-0260_suppl.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-scan' was
changed to 'multi-scan' in accordance with the built-in table derived
from the CIF Core dictionary named 'cif_core.dic' version 2.4.5 last
updated on 2014-11-21.

Automatic conversion script
Id: cif_fix_values 8738 2021-04-28 16:35:53Z antanas 
;
_cod_original_cell_volume        1573.8(16)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               8106522
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 0.81731(18) 0.04681(5) 0.03899(9) 0.0450(3) Uani 1 1 d . . .
O2 O 0.24927(19) 0.14743(6) -0.00338(10) 0.0555(3) Uani 1 1 d . . .
O3 O 0.6841(3) -0.02879(7) 0.38591(10) 0.0603(4) Uani 1 1 d . . .
O4 O 0.4245(2) 0.29825(7) -0.41674(11) 0.0620(4) Uani 1 1 d . . .
O5 O 1.0797(2) -0.07186(8) 0.38235(13) 0.0778(5) Uani 1 1 d . . .
N1 N 1.1884(2) -0.13821(7) 0.52500(12) 0.0528(4) Uani 1 1 d . . .
C3 C 0.4208(2) 0.11598(7) 0.00910(13) 0.0393(4) Uani 1 1 d . . .
C2 C 0.5740(2) 0.11801(7) -0.07069(12) 0.0369(3) Uani 1 1 d . . .
C1 C 0.7562(3) 0.08292(8) -0.05095(13) 0.0416(4) Uani 1 1 d . . .
H1 H 0.8508 0.0836 -0.1053 0.050 Uiso 1 1 calc R . .
C8 C 0.6824(2) 0.04455(7) 0.11793(12) 0.0379(3) Uani 1 1 d . . .
C9 C 0.4838(2) 0.07579(7) 0.10446(12) 0.0379(3) Uani 1 1 d . . .
C4 C 0.3530(3) 0.06823(8) 0.18806(14) 0.0460(4) Uani 1 1 d . . .
H4 H 0.2149 0.0882 0.1809 0.055 Uiso 1 1 calc R . .
C5 C 0.4208(3) 0.03271(8) 0.27948(14) 0.0495(4) Uani 1 1 d . . .
H5 H 0.3290 0.0276 0.3344 0.059 Uiso 1 1 calc R . .
C6 C 0.6256(3) 0.00383(8) 0.29236(13) 0.0448(4) Uani 1 1 d . . .
C7 C 0.7566(3) 0.00904(8) 0.21086(13) 0.0439(4) Uani 1 1 d . . .
H7 H 0.8942 -0.0112 0.2181 0.053 Uiso 1 1 calc R . .
C10 C 0.5389(2) 0.16251(7) -0.16570(12) 0.0377(3) Uani 1 1 d . . .
C11 C 0.3374(3) 0.16942(8) -0.22656(13) 0.0426(4) Uani 1 1 d . . .
H11 H 0.2214 0.1429 -0.2100 0.051 Uiso 1 1 calc R . .
C12 C 0.3033(3) 0.21410(8) -0.31047(13) 0.0461(4) Uani 1 1 d . . .
H12 H 0.1646 0.2180 -0.3509 0.055 Uiso 1 1 calc R . .
C13 C 0.7059(3) 0.20154(8) -0.19404(13) 0.0422(4) Uani 1 1 d . . .
H13 H 0.8452 0.1974 -0.1543 0.051 Uiso 1 1 calc R . .
C14 C 0.6740(3) 0.24612(8) -0.27862(13) 0.0451(4) Uani 1 1 d . . .
H14 H 0.7908 0.2716 -0.2973 0.054 Uiso 1 1 calc R . .
C15 C 0.4706(3) 0.25334(8) -0.33597(13) 0.0437(4) Uani 1 1 d . . .
C16 C 1.2151(3) -0.10627(9) 0.43563(16) 0.0592(5) Uani 1 1 d . . .
H16 H 1.3513 -0.1101 0.4099 0.071 Uiso 1 1 calc R . .
C17 C 0.9888(4) -0.13386(14) 0.5720(2) 0.0841(7) Uani 1 1 d . . .
H17A H 0.9006 -0.0985 0.5367 0.126 Uiso 1 1 calc R . .
H17B H 1.0200 -0.1249 0.6501 0.126 Uiso 1 1 calc R . .
H17C H 0.9106 -0.1753 0.5611 0.126 Uiso 1 1 calc R . .
C18 C 1.3566(4) -0.17971(10) 0.58000(19) 0.0746(6) Uani 1 1 d . . .
H18A H 1.4843 -0.1775 0.5417 0.112 Uiso 1 1 calc R . .
H18B H 1.3051 -0.2249 0.5803 0.112 Uiso 1 1 calc R . .
H18C H 1.3938 -0.1646 0.6551 0.112 Uiso 1 1 calc R . .
H4A H 0.553(5) 0.3185(13) -0.436(2) 0.106(9) Uiso 1 1 d . . .
H3A H 0.815(4) -0.0410(11) 0.3872(19) 0.083(8) Uiso 1 1 d . . .
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'
N N 0.0061 0.0033 '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
C1 O1 C8 118.04(13) . .
C6 O3 H3A 108.5(16) . .
C15 O4 H4A 111.6(15) . .
C16 N1 C17 121.06(17) . .
C16 N1 C18 121.62(18) . .
C17 N1 C18 117.32(18) . .
O2 C3 C9 122.41(15) . .
O2 C3 C2 122.01(15) . .
C9 C3 C2 115.57(14) . .
C1 C2 C3 118.39(14) . .
C1 C2 C10 120.72(14) . .
C3 C2 C10 120.64(14) . .
C2 C1 O1 126.05(15) . .
C2 C1 H1 117.0 . .
O1 C1 H1 117.0 . .
O1 C8 C9 121.38(14) . .
O1 C8 C7 115.84(14) . .
C9 C8 C7 122.77(15) . .
C8 C9 C4 117.08(14) . .
C8 C9 C3 120.41(14) . .
C4 C9 C3 122.48(14) . .
C5 C4 C9 121.25(16) . .
C5 C4 H4 119.4 . .
C9 C4 H4 119.4 . .
C4 C5 C6 120.21(16) . .
C4 C5 H5 119.9 . .
C6 C5 H5 119.9 . .
O3 C6 C7 122.93(16) . .
O3 C6 C5 116.95(16) . .
C7 C6 C5 120.11(15) . .
C6 C7 C8 118.50(15) . .
C6 C7 H7 120.7 . .
C8 C7 H7 120.7 . .
C11 C10 C13 117.54(14) . .
C11 C10 C2 121.77(14) . .
C13 C10 C2 120.62(14) . .
C12 C11 C10 121.29(15) . .
C12 C11 H11 119.4 . .
C10 C11 H11 119.4 . .
C11 C12 C15 120.25(15) . .
C11 C12 H12 119.9 . .
C15 C12 H12 119.9 . .
C14 C13 C10 121.66(14) . .
C14 C13 H13 119.2 . .
C10 C13 H13 119.2 . .
C13 C14 C15 119.67(15) . .
C13 C14 H14 120.2 . .
C15 C14 H14 120.2 . .
O4 C15 C14 123.05(15) . .
O4 C15 C12 117.40(15) . .
C14 C15 C12 119.55(15) . .
O5 C16 N1 125.8(2) . .
O5 C16 H16 117.1 . .
N1 C16 H16 117.1 . .
N1 C17 H17A 109.5 . .
N1 C17 H17B 109.5 . .
H17A C17 H17B 109.5 . .
N1 C17 H17C 109.5 . .
H17A C17 H17C 109.5 . .
H17B C17 H17C 109.5 . .
N1 C18 H18A 109.5 . .
N1 C18 H18B 109.5 . .
H18A C18 H18B 109.5 . .
N1 C18 H18C 109.5 . .
H18A C18 H18C 109.5 . .
H18B C18 H18C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C1 1.3517(19) .
O1 C8 1.370(2) .
O2 C3 1.2448(19) .
O3 C6 1.348(2) .
O3 H3A 0.85(2) .
O4 C15 1.362(2) .
O4 H4A 0.96(3) .
O5 C16 1.229(2) .
N1 C16 1.314(2) .
N1 C17 1.445(3) .
N1 C18 1.454(2) .
C3 C9 1.453(2) .
C3 C2 1.461(2) .
C2 C1 1.344(2) .
C2 C10 1.482(2) .
C1 H1 0.9500 .
C8 C9 1.389(2) .
C8 C7 1.391(2) .
C9 C4 1.406(2) .
C4 C5 1.368(2) .
C4 H4 0.9500 .
C5 C6 1.402(3) .
C5 H5 0.9500 .
C6 C7 1.382(2) .
C7 H7 0.9500 .
C10 C11 1.393(2) .
C10 C13 1.395(2) .
C11 C12 1.381(2) .
C11 H11 0.9500 .
C12 C15 1.387(2) .
C12 H12 0.9500 .
C13 C14 1.384(2) .
C13 H13 0.9500 .
C14 C15 1.386(2) .
C14 H14 0.9500 .
C16 H16 0.9500 .
C17 H17A 0.9800 .
C17 H17B 0.9800 .
C17 H17C 0.9800 .
C18 H18A 0.9800 .
C18 H18B 0.9800 .
C18 H18C 0.9800 .
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 O5 0.85(2) 1.78(3) 2.634(2) 175(2) .
O4 H4A O2 0.96(3) 1.72(3) 2.658(2) 166(2) 4_665
