#------------------------------------------------------------------------------
#$Date: 2019-12-26 20:00:19 +0200 (Thu, 26 Dec 2019) $
#$Revision: 246032 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/18/2021872.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_2021872
loop_
_publ_author_name
'Li, S.'
'Lundquist, K.'
'Stomberg, R.'
_publ_section_title
;
 An investigation of 2,4'-dihydroxy-3,3'-dimethoxy-5'-methylstilbene using
 X-ray crystallography and NMR spectroscopy
;
_journal_issue                   6
_journal_name_full
'Acta Crystallographica Section C Crystal Structure Communications'
_journal_page_first              1012
_journal_paper_doi               10.1107/S0108270199000670
_journal_volume                  55
_journal_year                    1999
_chemical_formula_moiety         'C17 H18 O4'
_chemical_formula_sum            'C17 H18 O4'
_chemical_formula_weight         286.31
_chemical_melting_point          397.5(5)
_chemical_name_systematic
;
 (E)-2,4'-dihydroxy-3,3'-dimethoxy-5'-methylstilbene
;
_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_H-M   'P 1 21/n 1'
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 90.3970(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.43410(10)
_cell_length_b                   15.5112(3)
_cell_length_c                   11.42930(10)
_cell_measurement_reflns_used    7340
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.39
_cell_measurement_theta_min      2.21
_cell_volume                     1495.18(4)
_computing_cell_refinement       'SAINT (Siemens, 1994a)'
_computing_data_collection       'SMART (Siemens, 1994a)'
_computing_data_reduction        'SAINT and XPREP (Siemens, 1996)'
_computing_molecular_graphics    'XP (Siemens, 1994b)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Siemens SMART CCD'
_diffrn_measurement_method       'ω oscillation 0.30°; 30 s/frame'
_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  0.036
_diffrn_reflns_av_sigmaI/netI    0.021
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            15404
_diffrn_reflns_theta_full        26.39
_diffrn_reflns_theta_max         26.39
_diffrn_reflns_theta_min         2.21
_diffrn_standards_decay_%        0
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.272
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.27
_refine_diff_density_max         0.16
_refine_diff_density_min         -0.14
_refine_ls_extinction_coef       0.0103(16)
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 1997)'
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    'H atoms: see below'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     196
_refine_ls_number_reflns         3064
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.053
_refine_ls_R_factor_all          0.057
_refine_ls_R_factor_gt           0.043
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0577P)²+0.3262P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.127
_reflns_number_gt                2411
_reflns_number_total             3064
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bm1301sup1.cif
_cod_data_source_block           2a
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value '397-398 K' was changed to
'397.5(5)' -- the average value was taken and precision was
estimated.

data item '_exptl_crystal_density_meas' value 'not measured' was
changed to '?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2021872
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_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_type_symbol
C1 -0.14294(17) 0.55026(10) 0.38418(13) 0.0470(4) Uani d . 1 C
C2 -0.23409(18) 0.52109(9) 0.47683(13) 0.0466(4) Uani d . 1 C
C3 -0.32209(18) 0.57809(10) 0.54510(13) 0.0484(4) Uani d . 1 C
C4 -0.31839(19) 0.66495(10) 0.52238(14) 0.0517(4) Uani d . 1 C
H4 -0.3777 0.7027 0.5678 0.062 Uiso calc R 1 H
C5 -0.22569(19) 0.69686(10) 0.43115(14) 0.0523(4) Uani d . 1 C
C6 -0.14004(19) 0.63942(10) 0.36368(14) 0.0518(4) Uani d . 1 C
H6 -0.0786 0.6606 0.3028 0.062 Uiso calc R 1 H
C7 -0.05650(19) 0.48656(10) 0.31503(13) 0.0520(4) Uani d . 1 C
H7 -0.0618 0.4301 0.3419 0.062 Uiso calc R 1 H
C8 0.02823(19) 0.49853(10) 0.21930(13) 0.0533(4) Uani d . 1 C
H8 0.0376 0.5548 0.1919 0.064 Uiso calc R 1 H
C9 -0.4977(2) 0.58911(13) 0.70908(15) 0.0668(5) Uani d . 1 C
H9A -0.4286 0.6271 0.7518 0.100 Uiso calc R 1 H
H9B -0.5530 0.5525 0.7628 0.100 Uiso calc R 1 H
H9C -0.5730 0.6225 0.6649 0.100 Uiso calc R 1 H
C10 -0.2175(2) 0.79217(11) 0.40871(18) 0.0696(5) Uani d . 1 C
H10A -0.1166 0.8138 0.4347 0.104 Uiso calc R 1 H
H10B -0.3006 0.8207 0.4507 0.104 Uiso calc R 1 H
H10C -0.2300 0.8029 0.3264 0.104 Uiso calc R 1 H
C11 0.10875(18) 0.43070(10) 0.15261(13) 0.0492(4) Uani d . 1 C
C12 0.10900(18) 0.34484(10) 0.18964(12) 0.0487(4) Uani d . 1 C
H12 0.0597 0.3305 0.2595 0.058 Uiso calc R 1 H
C13 0.18068(18) 0.28108(10) 0.12501(13) 0.0480(4) Uani d . 1 C
C14 0.25616(19) 0.30167(11) 0.01965(14) 0.0529(4) Uani d . 1 C
C15 0.2576(2) 0.38598(11) -0.01683(15) 0.0629(5) Uani d . 1 C
H15 0.3077 0.4004 -0.0864 0.075 Uiso calc R 1 H
C16 0.1851(2) 0.44997(11) 0.04876(14) 0.0596(4) Uani d . 1 C
H16 0.1879 0.5067 0.0226 0.072 Uiso calc R 1 H
C17 0.1007(3) 0.16916(12) 0.25602(16) 0.0721(5) Uani d . 1 C
H17A 0.1406 0.1987 0.3239 0.108 Uiso calc R 1 H
H17B 0.1125 0.1081 0.2666 0.108 Uiso calc R 1 H
H17C -0.0094 0.1828 0.2451 0.108 Uiso calc R 1 H
O1 -0.23996(15) 0.43474(7) 0.50100(10) 0.0600(3) Uani d . 1 O
H1 -0.2915 0.4269 0.5606 0.090 Uiso calc R 1 H
O2 -0.40643(14) 0.53740(8) 0.63122(10) 0.0630(3) Uani d . 1 O
O3 0.18717(15) 0.19560(7) 0.15603(10) 0.0643(3) Uani d . 1 O
O4 0.32827(17) 0.24074(8) -0.04786(11) 0.0720(4) Uani d . 1 O
H4A 0.3156 0.1930 -0.0185 0.108 Uiso calc R 1 H
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_publ_flag
C2 C1 C6 117.32(13) ?
C2 C1 C7 118.20(10) ?
C6 C1 C7 124.50(10) ?
O1 C2 C1 119.60(10) ?
O1 C2 C3 119.13(13) ?
C1 C2 C3 121.27(14) ?
O2 C3 C4 126.90(10) yes
O2 C3 C2 112.95(14) ?
C4 C3 C2 120.20(14) ?
C3 C4 C5 120.14(14) ?
C6 C5 C4 118.95(14) ?
C6 C5 C10 120.88(15) ?
C4 C5 C10 120.2(2) ?
C5 C6 C1 122.10(14) ?
C8 C7 C1 128.7(2) yes
C7 C8 C11 125.6(2) yes
C16 C11 C12 117.70(14) ?
C16 C11 C8 120.59(14) ?
C12 C11 C8 121.70(10) ?
C13 C12 C11 121.46(14) ?
O3 C13 C12 124.90(10) yes
O3 C13 C14 115.08(13) ?
C12 C13 C14 120.04(14) ?
O4 C14 C15 118.87(14) ?
O4 C14 C13 122.30(10) ?
C15 C14 C13 118.85(14) ?
C14 C15 C16 120.83(15) ?
C11 C16 C15 121.12(15) ?
C3 O2 C9 118.30(10) ?
C13 O3 C17 117.80(10) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 1.389(2) ?
C1 C6 1.403(2) ?
C1 C7 1.463(2) yes
C2 O1 1.369(2) ?
C2 C3 1.396(2) ?
C3 O2 1.372(2) ?
C3 C4 1.373(2) ?
C4 C5 1.398(2) ?
C5 C6 1.385(2) ?
C5 C10 1.502(2) ?
C7 C8 1.324(2) yes
C8 C11 1.468(2) yes
C9 O2 1.428(2) ?
C11 C16 1.387(2) ?
C11 C12 1.397(2) ?
C12 C13 1.377(2) ?
C13 O3 1.374(2) ?
C13 C14 1.403(2) ?
C14 O4 1.366(2) ?
C14 C15 1.373(2) ?
C15 C16 1.388(2) ?
C17 O3 1.420(2) ?
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_publ_flag
C6 C1 C2 O1 -179.53(14) ?
C7 C1 C2 O1 0.3(2) ?
C6 C1 C2 C3 1.4(2) ?
C7 C1 C2 C3 -178.76(14) ?
O1 C2 C3 O2 0.0(2) ?
C1 C2 C3 O2 179.04(13) ?
O1 C2 C3 C4 -179.85(14) ?
C1 C2 C3 C4 -0.8(2) ?
O2 C3 C4 C5 179.81(15) ?
C2 C3 C4 C5 -0.4(2) ?
C3 C4 C5 C6 0.9(2) ?
C3 C4 C5 C10 -178.02(16) ?
C4 C5 C6 C1 -0.2(2) ?
C10 C5 C6 C1 178.68(16) ?
C2 C1 C6 C5 -0.9(2) ?
C7 C1 C6 C5 179.26(15) ?
C2 C1 C7 C8 175.1(2) ?
C6 C1 C7 C8 -5.1(3) yes
C1 C7 C8 C11 -178.3(2) yes
C7 C8 C11 C16 175.4(2) ?
C7 C8 C11 C12 -3.4(3) yes
C16 C11 C12 C13 -0.8(2) ?
C8 C11 C12 C13 178.06(15) ?
C11 C12 C13 O3 179.38(15) ?
C11 C12 C13 C14 0.2(2) ?
O3 C13 C14 O4 1.1(2) ?
C12 C13 C14 O4 -179.68(15) ?
O3 C13 C14 C15 -178.92(16) ?
C12 C13 C14 C15 0.3(3) ?
O4 C14 C15 C16 179.71(17) ?
C13 C14 C15 C16 -0.3(3) ?
C12 C11 C16 C15 0.8(3) ?
C8 C11 C16 C15 -178.05(16) ?
C14 C15 C16 C11 -0.3(3) ?
C4 C3 O2 C9 -1.9(2) ?
C2 C3 O2 C9 178.25(14) ?
C12 C13 O3 C17 6.5(2) ?
C14 C13 O3 C17 -174.33(16) ?
