#------------------------------------------------------------------------------
#$Date: 2019-11-22 18:46:19 +0200 (Fri, 22 Nov 2019) $
#$Revision: 231217 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/51/62/4516268.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_4516268
loop_
_publ_author_name
'White, Nicholas G.'
'Carta, Veronica'
'MacLachlan, Mark J.'
_publ_section_title
;
 Layered 2D Sheetlike Supramolecular Polymers Formed by
 O--H···Anion Hydrogen Bonds
;
_journal_issue                   3
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              1540
_journal_paper_doi               10.1021/acs.cgd.5b00062
_journal_volume                  15
_journal_year                    2015
_chemical_compound_source        synthesized
_chemical_formula_moiety         'C18 H14 O6, 4(H2 O)'
_chemical_formula_sum            'C18 H22 O10'
_chemical_formula_weight         398.37
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     other
_cell_angle_alpha                90
_cell_angle_beta                 99.826(8)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   19.048(9)
_cell_length_b                   7.493(4)
_cell_length_c                   6.555(3)
_cell_measurement_reflns_used    4049
_cell_measurement_temperature    90
_cell_measurement_theta_max      27.97
_cell_measurement_theta_min      3.26
_cell_volume                     921.8(8)
_computing_cell_refinement       'Apex2, (Bruker, 2007)'
_computing_data_collection       'Apex2, (Bruker, 2007)'
_computing_data_reduction        'Apex2, (Bruker, 2007)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_diffrn_ambient_temperature      90
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.950
_diffrn_measurement_device       Serial
_diffrn_measurement_device_type  'Bruker Apex Duo'
_diffrn_measurement_method       ω/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.033
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            8025
_diffrn_reflns_theta_full        25.928
_diffrn_reflns_theta_max         28.182
_diffrn_reflns_theta_min         2.170
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.118
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.842
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Apex2, (Bruker, 2007)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.435
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             420
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.23
_refine_diff_density_min         -0.23
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   1.0329
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     127
_refine_ls_number_reflns         1605
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0533
_refine_ls_R_factor_gt           0.0469
_refine_ls_shift/su_max          0.0001801
_refine_ls_shift/su_mean         0.0000152
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)] 
 where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)²]² 
 Ai are: 
 2.82 4.16 1.91 0.498 -0.165E-01 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1178
_refine_ls_wR_factor_gt          0.1165
_refine_ls_wR_factor_ref         0.1172
_reflns_limit_h_max              24
_reflns_limit_h_min              -25
_reflns_limit_k_max              9
_reflns_limit_k_min              0
_reflns_limit_l_max              8
_reflns_limit_l_min              0
_reflns_number_gt                1461
_reflns_number_total             2156
_reflns_threshold_expression     I>2.0σ(I)
_oxford_diffrn_Wilson_B_factor   2.91
_oxford_diffrn_Wilson_scale      22.91
_oxford_refine_ls_r_factor_ref   0.0510
_oxford_refine_ls_scale          0.1820(2)
_oxford_reflns_number_all        1648
_oxford_reflns_threshold_expression_ref I>-3.0\s(I)
_cod_data_source_file            cg5b00062_si_002.cif
_cod_data_source_block           1
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_atom_sites_solution_primary' value 'Other' was changed to
'other' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/ACS/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_original_cell_volume        921.8(7)
_cod_original_sg_symbol_H-M      'P 21/c '
_cod_database_code               4516268
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,-y,-z
x,-y+1/2,z+1/2
-x,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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_disorder_group
C1 C 0.26752(10) 0.6598(2) 0.1223(3) 0.0285 1.0000 Uani . .
C2 C 0.30464(9) 0.4998(2) 0.1523(3) 0.0284 1.0000 Uani . .
C3 C 0.26741(10) 0.3403(2) 0.1449(3) 0.0284 1.0000 Uani . .
C4 C 0.19345(10) 0.3393(2) 0.1103(3) 0.0291 1.0000 Uani . .
C5 C 0.15539(9) 0.5000(2) 0.0776(3) 0.0272 1.0000 Uani . .
C6 C 0.19344(9) 0.6606(2) 0.0833(3) 0.0284 1.0000 Uani . .
C7 C 0.07571(9) 0.5000(2) 0.0382(3) 0.0267 1.0000 Uani . .
C8 C 0.03723(10) 0.6191(3) -0.1022(3) 0.0346 1.0000 Uani . .
C9 C -0.03722(10) 0.6190(3) -0.1386(3) 0.0346 1.0000 Uani . .
O2 O 0.37911(7) 0.49995(18) 0.1892(2) 0.0367 1.0000 Uani . .
O1 O 0.30592(7) 0.81520(18) 0.1330(2) 0.0416 1.0000 Uani . .
O3 O 0.30581(7) 0.18472(18) 0.1729(2) 0.0415 1.0000 Uani . .
O22 O 0.44200(8) 0.3663(2) 0.5721(3) 0.0524 1.0000 Uani . .
O21 O 0.44209(8) 0.8664(2) 0.3701(3) 0.0520 1.0000 Uani . .
H41 H 0.1690 0.2299 0.1063 0.0336 1.0000 Uiso R .
H61 H 0.1683 0.7689 0.0612 0.0322 1.0000 Uiso R .
H81 H 0.0617 0.7004 -0.1763 0.0396 1.0000 Uiso R .
H91 H -0.0616 0.6996 -0.2378 0.0405 1.0000 Uiso R .
H31 H 0.2781 0.1063 0.1317 0.0620 0.5000 Uiso R 1
H211 H 0.4318 0.9129 0.4755 0.0758 0.5000 Uiso R 1
H26 H 0.3929 0.5196 0.0748 0.0528 0.5000 Uiso . 2
H227 H 0.4765 0.3001 0.5775 0.0768 0.5000 Uiso . 2
H212 H 0.4774 0.7970 0.4053 0.0754 0.5000 Uiso R 1
H21 H 0.3915 0.4740 0.3119 0.0528 0.5000 Uiso R 1
H11 H 0.3476 0.7924 0.1828 0.0606 0.5000 Uiso R 1
H222 H 0.4107 0.2989 0.5978 0.0766 0.5000 Uiso R 1
H226 H 0.4280 0.4145 0.4587 0.0769 0.5000 Uiso . 2
H16 H 0.2825 0.8978 0.1101 0.0329 0.5000 Uiso . 2
H221 H 0.4514 0.4441 0.6598 0.0767 0.5000 Uiso R 1
H216 H 0.4064 0.8033 0.3488 0.0759 0.5000 Uiso . 2
H217 H 0.4492 0.9269 0.2717 0.0757 0.5000 Uiso . 2
H36 H 0.3438 0.2119 0.1292 0.0631 0.5000 Uiso . 2
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 . C1 C6 . 120.38(15) yes
C2 . C1 O1 . 118.15(16) yes
C6 . C1 O1 . 121.47(15) yes
C1 . C2 C3 . 119.62(15) yes
C1 . C2 O2 . 120.07(15) yes
C3 . C2 O2 . 120.31(15) yes
C2 . C3 C4 . 120.61(15) yes
C2 . C3 O3 . 118.05(16) yes
C4 . C3 O3 . 121.35(15) yes
C3 . C4 C5 . 120.27(15) yes
C3 . C4 H41 . 119.5 no
C5 . C4 H41 . 120.2 no
C4 . C5 C6 . 118.75(15) yes
C4 . C5 C7 . 120.64(15) yes
C6 . C5 C7 . 120.61(15) yes
C5 . C6 C1 . 120.35(15) yes
C5 . C6 H61 . 119.2 no
C1 . C6 H61 . 120.4 no
C5 . C7 C9 2_565 121.34(16) yes
C5 . C7 C8 . 121.12(16) yes
C9 2_565 C7 C8 . 117.54(16) yes
C7 . C8 C9 . 121.03(17) yes
C7 . C8 H81 . 120.0 no
C9 . C8 H81 . 119.0 no
C8 . C9 C7 2_565 121.43(17) yes
C8 . C9 H91 . 118.7 no
C7 2_565 C9 H91 . 119.8 no
C2 . O2 H21 . 106.4 no
C1 . O1 H11 . 108.3 no
C3 . O3 H31 . 105.8 no
H222 . O22 H221 . 112.0 no
H211 . O21 H212 . 108.7 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 . 1.389(3) yes
C1 C6 . 1.390(3) yes
C1 O1 . 1.370(2) yes
C2 C3 . 1.386(3) yes
C2 O2 . 1.398(2) yes
C3 C4 . 1.388(3) yes
C3 O3 . 1.372(2) yes
C4 C5 . 1.403(3) yes
C4 H41 . 0.941 no
C5 C6 . 1.402(3) yes
C5 C7 . 1.495(2) yes
C6 H61 . 0.941 no
C7 C9 2_565 1.389(3) yes
C7 C8 . 1.396(3) yes
C8 C9 . 1.397(3) yes
C8 H81 . 0.949 no
C9 H91 . 0.949 no
O2 H21 . 0.822 no
O1 H11 . 0.823 no
O3 H31 . 0.805 no
O22 H222 . 0.820 no
O22 H221 . 0.817 no
O21 H211 . 0.827 no
O21 H212 . 0.850 no
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_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
O3 H31 O1 1_545 124.58(5) 0.805 2.244 2.781(3) yes
O21 H211 O2 3_565 163.07(6) 0.827 1.969 2.770(3) yes
O2 H26 O21 3_564 159.61(11) 0.849 1.959 2.770(3) yes
O22 H227 O21 2_666 172.12(13) 0.820 1.973 2.788(3) yes
O21 H212 O22 2_666 168.77(7) 0.850 1.949 2.788(3) yes
O2 H21 O22 . 162.68(6) 0.822 1.981 2.776(3) yes
O1 H11 O21 . 149.39(6) 0.823 2.074 2.813(3) yes
O22 H222 O2 3_555 147.22(5) 0.820 2.421 3.142(3) yes
O22 H222 O3 3_555 138.67(6) 0.820 2.142 2.810(3) yes
O22 H226 O2 . 169.28(11) 0.828 1.958 2.776(3) yes
O1 H16 O3 1_565 131.15(11) 0.762 2.220 2.781(3) yes
O22 H221 O21 3_565 162.41(7) 0.817 2.008 2.798(3) yes
O21 H216 O2 . 134.24(12) 0.819 2.519 3.146(3) yes
O21 H216 O1 . 134.23(13) 0.819 2.180 2.813(3) yes
O21 H217 O22 3_564 159.15(12) 0.819 2.017 2.798(3) yes
O3 H36 O22 3_554 148.14(11) 0.847 2.055 2.810(3) yes
loop_
_oxford_refln_omitted_index_h
_oxford_refln_omitted_index_k
_oxford_refln_omitted_index_l
_oxford_refln_omitted_flag
-23 4 2 x
0 2 0 x
-1 0 2 x
1 0 2 x
-1 0 4 x
-3 0 4 x
