#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/72/2217200.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_2217200
loop_
_publ_author_name
'Hong, Won Ki'
'Heo, Ji Youn'
'Han, Byung Hee'
'Sung, Chang Keun'
'Kang, Sung Kwon'
_publ_section_title
;
 3,4-Dihydroxyphenyl 3,4,5-trimethoxybenzoate
;
_journal_coeditor_code           LX2033
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o49
_journal_page_last               o49
_journal_paper_doi               10.1107/S1600536807062009
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C16 H16 O7'
_chemical_formula_moiety         'C16 H16 O7'
_chemical_formula_sum            'C16 H16 O7'
_chemical_formula_weight         320.29
_chemical_name_systematic
;
3,4-Dihydroxyphenyl 3,4,5-trimethoxybenzoate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 105.57(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   11.552(2)
_cell_length_b                   12.817(3)
_cell_length_c                   10.572(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      14.23
_cell_measurement_theta_min      11.36
_cell_volume                     1507.9(6)
_computing_cell_refinement       'CAD-4 Express (Enraf--Nonius, 1994)'
_computing_data_collection       'CAD-4 Express (Enraf--Nonius, 1994)'
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics
'ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 1998)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       'Non-profiled ω/2θ scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0297
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       2
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            4251
_diffrn_reflns_theta_full        27.47
_diffrn_reflns_theta_max         27.47
_diffrn_reflns_theta_min         2.42
_diffrn_standards_decay_%        2
_diffrn_standards_interval_count 400
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.112
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.411
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             672
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.231
_refine_diff_density_min         -0.201
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     219
_refine_ls_number_reflns         3444
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.015
_refine_ls_R_factor_gt           0.0502
_refine_ls_shift/su_max          0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0489P)²+0.3432P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.1257
_reflns_number_gt                2176
_reflns_number_total             3444
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            lx2033.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2217200
_cod_database_fobs_code          2217200
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
O O1 -0.00088(14) -0.18103(12) 0.14141(16) 0.0519(4) Uani d . 1
O O2 0.09341(15) -0.33144(11) 0.01850(15) 0.0509(4) Uani d . 1
O O3 0.27941(14) -0.29798(11) -0.07081(15) 0.0463(4) Uani d . 1
O O4 0.41661(13) 0.07744(11) 0.09149(15) 0.0434(4) Uani d . 1
O O5 0.24027(13) 0.13828(11) 0.11272(16) 0.0482(4) Uani d . 1
O O6 0.24533(18) 0.48003(14) -0.05695(17) 0.0619(5) Uani d . 1
H H6O 0.261(3) 0.541(3) -0.030(3) 0.107(12) Uiso d . 1
O O7 0.39231(17) 0.54885(12) 0.17566(19) 0.0554(5) Uani d . 1
H H7O 0.448(3) 0.556(2) 0.244(3) 0.083(11) Uiso d . 1
C C1 0.25245(18) -0.04039(15) 0.07245(19) 0.0339(5) Uani d . 1
C C2 0.15217(18) -0.05794(16) 0.1181(2) 0.0374(5) Uani d . 1
H H2 0.1214 -0.0047 0.1594 0.045 Uiso calc R 1
C C3 0.09822(18) -0.15538(17) 0.1017(2) 0.0384(5) Uani d . 1
C C4 0.14486(19) -0.23470(15) 0.0401(2) 0.0369(5) Uani d . 1
C C5 0.24393(19) -0.21565(15) -0.00864(19) 0.0348(5) Uani d . 1
C C6 0.29865(18) -0.11831(15) 0.0089(2) 0.0350(5) Uani d . 1
H H6 0.3657 -0.1054 -0.0216 0.042 Uiso calc R 1
C C7 0.31335(19) 0.06225(15) 0.09277(19) 0.0353(5) Uani d . 1
C C8 0.28605(19) 0.24148(15) 0.1316(2) 0.0388(5) Uani d . 1
C C9 0.2473(2) 0.31040(16) 0.0299(2) 0.0421(5) Uani d . 1
H H9 0.1966 0.2881 -0.0495 0.05 Uiso calc R 1
C C10 0.28413(19) 0.41347(16) 0.0461(2) 0.0402(5) Uani d . 1
C C11 0.35900(18) 0.44546(15) 0.1663(2) 0.0383(5) Uani d . 1
C C12 0.3939(2) 0.37553(18) 0.2672(2) 0.0441(5) Uani d . 1
H H12 0.4424 0.3978 0.3478 0.053 Uiso calc R 1
C C13 0.3579(2) 0.27155(17) 0.2510(2) 0.0444(5) Uani d . 1
H H13 0.382 0.224 0.3194 0.053 Uiso calc R 1
C C14 -0.0468(2) -0.1053(2) 0.2138(2) 0.0520(6) Uani d . 1
H H14A 0.0153 -0.0851 0.2901 0.078 Uiso calc R 1
H H14B -0.1131 -0.1346 0.2405 0.078 Uiso calc R 1
H H14C -0.0737 -0.0452 0.1596 0.078 Uiso calc R 1
C C15 0.0859(2) -0.38926(18) 0.1315(3) 0.0591(7) Uani d . 1
H H15A 0.1518 -0.3706 0.2048 0.089 Uiso calc R 1
H H15B 0.0893 -0.4626 0.1141 0.089 Uiso calc R 1
H H15C 0.0115 -0.3735 0.1514 0.089 Uiso calc R 1
C C16 0.3815(2) -0.28499(19) -0.1210(3) 0.0572(7) Uani d . 1
H H16A 0.3659 -0.2304 -0.1855 0.086 Uiso calc R 1
H H16B 0.3971 -0.349 -0.1606 0.086 Uiso calc R 1
H H16C 0.4502 -0.2668 -0.0505 0.086 Uiso calc R 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 '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
C3 O1 C14 117.83(17) y
C4 O2 C15 116.87(18) y
C5 O3 C16 118.32(16) y
C7 O5 C8 118.20(16) y
C10 O6 H6O 109(2) ?
C11 O7 H7O 108(2) ?
C2 C1 C6 121.14(18) ?
C2 C1 C7 120.15(18) ?
C6 C1 C7 118.70(18) ?
C3 C2 C1 119.46(19) ?
C3 C2 H2 120.3 ?
C1 C2 H2 120.3 ?
O1 C3 C2 124.49(19) ?
O1 C3 C4 115.54(18) ?
C2 C3 C4 119.97(19) ?
O2 C4 C3 122.36(19) ?
O2 C4 C5 117.33(19) ?
C3 C4 C5 120.22(18) ?
O3 C5 C6 125.10(18) ?
O3 C5 C4 115.13(17) ?
C6 C5 C4 119.77(18) ?
C1 C6 C5 119.39(19) ?
C1 C6 H6 120.3 ?
C5 C6 H6 120.3 ?
O4 C7 O5 123.18(18) y
O4 C7 C1 124.89(19) ?
O5 C7 C1 111.93(17) y
C13 C8 C9 122.2(2) ?
C13 C8 O5 120.3(2) ?
C9 C8 O5 117.3(2) ?
C8 C9 C10 119.5(2) ?
C8 C9 H9 120.2 ?
C10 C9 H9 120.2 ?
O6 C10 C9 118.3(2) y
O6 C10 C11 122.40(19) ?
C9 C10 C11 119.3(2) ?
C12 C11 O7 123.8(2) ?
C12 C11 C10 119.94(19) ?
O7 C11 C10 116.3(2) y
C11 C12 C13 121.0(2) ?
C11 C12 H12 119.5 ?
C13 C12 H12 119.5 ?
C8 C13 C12 118.1(2) ?
C8 C13 H13 120.9 ?
C12 C13 H13 120.9 ?
O1 C14 H14A 109.5 ?
O1 C14 H14B 109.5 ?
H14A C14 H14B 109.5 ?
O1 C14 H14C 109.5 ?
H14A C14 H14C 109.5 ?
H14B C14 H14C 109.5 ?
O2 C15 H15A 109.5 ?
O2 C15 H15B 109.5 ?
H15A C15 H15B 109.5 ?
O2 C15 H15C 109.5 ?
H15A C15 H15C 109.5 ?
H15B C15 H15C 109.5 ?
O3 C16 H16A 109.5 ?
O3 C16 H16B 109.5 ?
H16A C16 H16B 109.5 ?
O3 C16 H16C 109.5 ?
H16A C16 H16C 109.5 ?
H16B C16 H16C 109.5 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C3 1.361(2) y
O1 C14 1.424(3) ?
O2 C4 1.367(2) y
O2 C15 1.428(3) ?
O3 C5 1.363(2) y
O3 C16 1.427(3) ?
O4 C7 1.212(2) y
O5 C7 1.343(2) y
O5 C8 1.419(2) y
O6 C10 1.362(3) y
O6 H6O 0.83(3) y
O7 C11 1.376(2) y
O7 H7O 0.84(3) y
C1 C2 1.388(3) ?
C1 C6 1.388(3) ?
C1 C7 1.480(3) ?
C2 C3 1.386(3) ?
C2 H2 0.93 ?
C3 C4 1.391(3) ?
C4 C5 1.397(3) ?
C5 C6 1.388(3) ?
C6 H6 0.93 ?
C8 C13 1.366(3) ?
C8 C9 1.371(3) ?
C9 C10 1.384(3) ?
C9 H9 0.93 ?
C10 C11 1.393(3) ?
C11 C12 1.369(3) ?
C12 C13 1.393(3) ?
C12 H12 0.93 ?
C13 H13 0.93 ?
C14 H14A 0.96 ?
C14 H14B 0.96 ?
C14 H14C 0.96 ?
C15 H15A 0.96 ?
C15 H15B 0.96 ?
C15 H15C 0.96 ?
C16 H16A 0.96 ?
C16 H16B 0.96 ?
C16 H16C 0.96 ?
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
O6 H6O O3 1_565 0.83(3) 2.13(4) 2.882(2) 150(3)
O7 H7O O4 2_655 0.84(3) 2.02(3) 2.855(3) 179(3)
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
C6 C1 C2 C3 0.9(3)
C7 C1 C2 C3 -178.15(18)
C14 O1 C3 C2 -5.1(3)
C14 O1 C3 C4 175.30(19)
C1 C2 C3 O1 -179.38(19)
C1 C2 C3 C4 0.2(3)
C15 O2 C4 C3 -60.4(3)
C15 O2 C4 C5 123.0(2)
O1 C3 C4 O2 1.2(3)
C2 C3 C4 O2 -178.35(19)
O1 C3 C4 C5 177.74(18)
C2 C3 C4 C5 -1.9(3)
C16 O3 C5 C6 0.8(3)
C16 O3 C5 C4 -178.79(19)
O2 C4 C5 O3 -1.2(3)
C3 C4 C5 O3 -177.91(18)
O2 C4 C5 C6 179.11(19)
C3 C4 C5 C6 2.4(3)
C2 C1 C6 C5 -0.3(3)
C7 C1 C6 C5 178.76(18)
O3 C5 C6 C1 179.05(18)
C4 C5 C6 C1 -1.3(3)
C8 O5 C7 O4 0.8(3)
C8 O5 C7 C1 -179.03(18)
C2 C1 C7 O4 158.2(2)
C6 C1 C7 O4 -21.0(3)
C2 C1 C7 O5 -22.1(3)
C6 C1 C7 O5 158.83(18)
C7 O5 C8 C13 -79.4(3)
C7 O5 C8 C9 105.9(2)
C13 C8 C9 C10 1.8(3)
O5 C8 C9 C10 176.44(19)
C8 C9 C10 O6 179.3(2)
C8 C9 C10 C11 -0.7(3)
O6 C10 C11 C12 179.1(2)
C9 C10 C11 C12 -0.9(3)
O6 C10 C11 O7 -0.1(3)
C9 C10 C11 O7 179.9(2)
O7 C11 C12 C13 -179.4(2)
C10 C11 C12 C13 1.5(3)
C9 C8 C13 C12 -1.3(3)
O5 C8 C13 C12 -175.74(19)
C11 C12 C13 C8 -0.4(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21119548
