#------------------------------------------------------------------------------
#$Date: 2020-03-20 07:55:45 +0200 (Fri, 20 Mar 2020) $
#$Revision: 249569 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/10/85/2108594.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_2108594
loop_
_publ_author_name
'Balakrishnan, C.'
'Manonmani, M.'
'Rafi Ahamed, S.'
'Vinitha, G.'
'Meenakshisundaram, S. P.'
'Sockalingam, R. M.'
_publ_section_title
;
 Supramolecular cocrystals of O---H···O
 hydrogen-bonded 18-crown-6 with isophthalic acid derivatives: Hirshfeld
 surface analysis and third-order nonlinear optical properties
;
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section B'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S2052520620001821
_journal_volume                  76
_journal_year                    2020
_chemical_formula_moiety         'C12 H24 O6, 2(C9 H6 O6), 2(H2 O)'
_chemical_formula_sum            'C30 H40 O20'
_chemical_formula_weight         720.62
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                77.133(4)
_cell_angle_beta                 79.494(4)
_cell_angle_gamma                84.408(4)
_cell_formula_units_Z            1
_cell_length_a                   7.5073(9)
_cell_length_b                   8.0208(9)
_cell_length_c                   14.7230(16)
_cell_measurement_reflns_used    9965
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      30.38
_cell_measurement_theta_min      2.87
_cell_volume                     848.29(17)
_computing_cell_refinement       'APEX3/SAINT (Bruker, 2016)'
_computing_data_collection       'APEX3(Bruker, 2016)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2016)'
_computing_molecular_graphics
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker axs kappa apex3 CMOS Diffractometer'
_diffrn_measurement_method       'ω and φ scan'
_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_unetI/netI     0.0147
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            24568
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         3.234
_exptl_absorpt_coefficient_mu    0.120
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.7141
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.411
_exptl_crystal_description       block
_exptl_crystal_F_000             380
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_refine_diff_density_max         0.199
_refine_diff_density_min         -0.244
_refine_diff_density_rms         0.044
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     237
_refine_ls_number_reflns         2965
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.0601
_refine_ls_R_factor_gt           0.0470
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0658P)²+0.4432P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1215
_refine_ls_wR_factor_ref         0.1396
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2384
_reflns_number_total             2965
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            aw5031sup1.cif
_cod_data_source_block           II
_cod_database_code               2108594
_publcif_datablock.id            {fa82224f-74af-4217-9fcd-18991f0ec280}
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.976
_shelx_estimated_absorpt_t_max   0.988
_publcif_info_exptl_table_max_cols 4
_publcif_info_exptl_table_use_headnotes n
_publcif_funding_html
;
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3047(5) 0.3435(5) 1.1019(3) 0.0932(11) Uani 1 1 d . . . . .
H1A H 0.3006 0.4440 1.1289 0.112 Uiso 1 1 calc R U . . .
H1B H 0.2170 0.2661 1.1419 0.112 Uiso 1 1 calc R U . . .
C2 C 0.2601(4) 0.3940(4) 1.0054(3) 0.0940(12) Uani 1 1 d . . . . .
H2A H 0.1562 0.4760 1.0050 0.113 Uiso 1 1 calc R U . . .
H2B H 0.3619 0.4489 0.9626 0.113 Uiso 1 1 calc R U . . .
C3 C 0.1832(5) 0.2927(5) 0.8802(3) 0.0973(12) Uani 1 1 d . . . . .
H3A H 0.2865 0.3462 0.8380 0.117 Uiso 1 1 calc R U . . .
H3B H 0.0789 0.3740 0.8770 0.117 Uiso 1 1 calc R U . . .
C4 C 0.1468(4) 0.1392(6) 0.8508(3) 0.1019(13) Uani 1 1 d . . . . .
H4A H 0.0566 0.0759 0.8982 0.122 Uiso 1 1 calc R U . . .
H4B H 0.0996 0.1710 0.7918 0.122 Uiso 1 1 calc R U . . .
C5 C 0.2860(6) -0.1241(5) 0.8200(2) 0.0907(11) Uani 1 1 d . . . . .
H5A H 0.2387 -0.1076 0.7614 0.109 Uiso 1 1 calc R U . . .
H5B H 0.1995 -0.1857 0.8705 0.109 Uiso 1 1 calc R U . . .
C6 C 0.4620(6) -0.2224(4) 0.81275(18) 0.0880(12) Uani 1 1 d . . . . .
H6A H 0.4504 -0.3274 0.7925 0.106 Uiso 1 1 calc R U . . .
H6B H 0.5509 -0.1559 0.7661 0.106 Uiso 1 1 calc R U . . .
C7 C 0.6904(2) 0.5953(2) 0.52059(13) 0.0310(4) Uani 1 1 d . . . . .
C8 C 0.6803(2) 0.4897(2) 0.61002(12) 0.0321(4) Uani 1 1 d . . . . .
H8 H 0.6234 0.5313 0.6628 0.038 Uiso 1 1 calc R U . . .
C9 C 0.7548(2) 0.3224(2) 0.62084(12) 0.0298(4) Uani 1 1 d . . . . .
C10 C 0.8386(2) 0.2612(2) 0.54153(12) 0.0316(4) Uani 1 1 d . . . . .
H10 H 0.8883 0.1492 0.5483 0.038 Uiso 1 1 calc R U . . .
C11 C 0.8487(2) 0.3663(2) 0.45171(12) 0.0313(4) Uani 1 1 d . . . . .
C12 C 0.7749(2) 0.5334(2) 0.44136(12) 0.0318(4) Uani 1 1 d . . . . .
H12 H 0.7819 0.6040 0.3816 0.038 Uiso 1 1 calc R U . . .
C13 C 0.6096(3) 0.7733(2) 0.51109(13) 0.0361(4) Uani 1 1 d . . . . .
C14 C 0.7493(2) 0.2070(2) 0.71626(12) 0.0332(4) Uani 1 1 d . . . . .
C15 C 0.9387(3) 0.3019(2) 0.36618(13) 0.0388(5) Uani 1 1 d . . . . .
O1 O 0.4783(3) 0.2627(2) 1.09713(12) 0.0662(5) Uani 1 1 d . . . . .
O2 O 0.2201(3) 0.2485(2) 0.97351(14) 0.0740(6) Uani 1 1 d . . . . .
O3 O 0.3117(3) 0.0342(3) 0.83875(12) 0.0718(6) Uani 1 1 d . . . . .
O4 O 0.6319(3) 0.86627(18) 0.42674(10) 0.0581(5) Uani 1 1 d . . . . .
H4 H 0.5804 0.9611 0.4275 0.087 Uiso 1 1 calc R U . . .
O5 O 0.5244(2) 0.82432(18) 0.58067(10) 0.0544(4) Uani 1 1 d . . . . .
O6 O 0.6712(2) 0.27946(17) 0.78535(9) 0.0492(4) Uani 1 1 d . . . . .
H6 H 0.6781 0.2131 0.8359 0.074 Uiso 1 1 calc R U . . .
O7 O 0.8140(2) 0.06026(17) 0.72783(9) 0.0454(4) Uani 1 1 d . . . . .
O8 O 1.0098(3) 0.1450(2) 0.38775(11) 0.0678(6) Uani 1 1 d . . . . .
H8A H 1.0526 0.1116 0.3391 0.102 Uiso 1 1 calc R U . . .
O9 O 0.9457(3) 0.3822(2) 0.28707(10) 0.0683(6) Uani 1 1 d . . . . .
O10 O 0.6836(2) 0.1087(2) 0.95193(10) 0.0553(4) Uani 1 1 d D . . . .
H10B H 0.616(3) 0.149(3) 0.9945(17) 0.074(9) Uiso 1 1 d D . . . .
H10A H 0.704(5) 0.001(2) 0.968(2) 0.111(13) Uiso 1 1 d 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'
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
_geom_angle_publ_flag
O1 C1 C2 108.7(2) . . ?
O1 C1 H1A 110.0 . . ?
C2 C1 H1A 110.0 . . ?
O1 C1 H1B 110.0 . . ?
C2 C1 H1B 110.0 . . ?
H1A C1 H1B 108.3 . . ?
O2 C2 C1 110.9(3) . . ?
O2 C2 H2A 109.5 . . ?
C1 C2 H2A 109.5 . . ?
O2 C2 H2B 109.5 . . ?
C1 C2 H2B 109.5 . . ?
H2A C2 H2B 108.0 . . ?
O2 C3 C4 109.6(3) . . ?
O2 C3 H3A 109.8 . . ?
C4 C3 H3A 109.8 . . ?
O2 C3 H3B 109.8 . . ?
C4 C3 H3B 109.8 . . ?
H3A C3 H3B 108.2 . . ?
O3 C4 C3 109.3(3) . . ?
O3 C4 H4A 109.8 . . ?
C3 C4 H4A 109.8 . . ?
O3 C4 H4B 109.8 . . ?
C3 C4 H4B 109.8 . . ?
H4A C4 H4B 108.3 . . ?
O3 C5 C6 108.3(2) . . ?
O3 C5 H5A 110.0 . . ?
C6 C5 H5A 110.0 . . ?
O3 C5 H5B 110.0 . . ?
C6 C5 H5B 110.0 . . ?
H5A C5 H5B 108.4 . . ?
O1 C6 C5 109.8(2) 2_657 . ?
O1 C6 H6A 109.7 2_657 . ?
C5 C6 H6A 109.7 . . ?
O1 C6 H6B 109.7 2_657 . ?
C5 C6 H6B 109.7 . . ?
H6A C6 H6B 108.2 . . ?
C8 C7 C12 120.02(16) . . ?
C8 C7 C13 119.20(16) . . ?
C12 C7 C13 120.78(16) . . ?
C9 C8 C7 120.33(16) . . ?
C9 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?
C10 C9 C8 119.38(16) . . ?
C10 C9 C14 119.08(15) . . ?
C8 C9 C14 121.53(15) . . ?
C9 C10 C11 120.53(16) . . ?
C9 C10 H10 119.7 . . ?
C11 C10 H10 119.7 . . ?
C12 C11 C10 119.85(16) . . ?
C12 C11 C15 119.23(16) . . ?
C10 C11 C15 120.91(16) . . ?
C11 C12 C7 119.88(16) . . ?
C11 C12 H12 120.1 . . ?
C7 C12 H12 120.1 . . ?
O5 C13 O4 123.58(17) . . ?
O5 C13 C7 120.62(17) . . ?
O4 C13 C7 115.79(16) . . ?
O7 C14 O6 123.47(17) . . ?
O7 C14 C9 122.94(16) . . ?
O6 C14 C9 113.58(15) . . ?
O9 C15 O8 123.47(18) . . ?
O9 C15 C11 124.48(18) . . ?
O8 C15 C11 112.05(16) . . ?
C1 O1 C6 112.1(3) . 2_657 ?
C3 O2 C2 112.0(3) . . ?
C5 O3 C4 113.2(3) . . ?
C13 O4 H4 109.5 . . ?
C14 O6 H6 109.5 . . ?
C15 O8 H8A 109.5 . . ?
H10B O10 H10A 112(2) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.395(4) . ?
C1 C2 1.479(5) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 O2 1.427(4) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 O2 1.412(4) . ?
C3 C4 1.457(6) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 O3 1.434(4) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 O3 1.396(4) . ?
C5 C6 1.471(5) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 O1 1.436(4) 2_657 ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.392(3) . ?
C7 C12 1.392(3) . ?
C7 C13 1.482(2) . ?
C8 C9 1.389(2) . ?
C8 H8 0.9300 . ?
C9 C10 1.388(2) . ?
C9 C14 1.497(2) . ?
C10 C11 1.395(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.386(3) . ?
C11 C15 1.490(2) . ?
C12 H12 0.9300 . ?
C13 O5 1.234(2) . ?
C13 O4 1.289(2) . ?
C14 O7 1.216(2) . ?
C14 O6 1.303(2) . ?
C15 O9 1.194(2) . ?
C15 O8 1.312(2) . ?
O1 C6 1.436(4) 2_657 ?
O4 H4 0.8200 . ?
O6 H6 0.8200 . ?
O8 H8A 0.8200 . ?
O10 H10B 0.833(17) . ?
O10 H10A 0.848(17) . ?
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
C2 H2B O1 0.97 2.61 3.441(4) 143.8 2_667
C6 H6B O7 0.97 2.66 3.519(4) 148.6 .
O4 H4 O5 0.82 1.81 2.628(2) 175.3 2_676
O6 H6 O10 0.82 1.73 2.542(2) 168.7 .
O8 H8A O7 0.82 1.96 2.7129(19) 151.8 2_756
O10 H10B O1 0.833(17) 2.013(17) 2.842(2) 173(3) .
O10 H10A O2 0.848(17) 2.065(19) 2.902(3) 169(3) 2_657
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 O2 74.3(3) . . . . ?
O2 C3 C4 O3 -70.1(4) . . . . ?
O3 C5 C6 O1 66.0(3) . . . 2_657 ?
C12 C7 C8 C9 0.2(3) . . . . ?
C13 C7 C8 C9 179.96(17) . . . . ?
C7 C8 C9 C10 -0.4(3) . . . . ?
C7 C8 C9 C14 178.74(16) . . . . ?
C8 C9 C10 C11 0.2(3) . . . . ?
C14 C9 C10 C11 -178.92(16) . . . . ?
C9 C10 C11 C12 0.1(3) . . . . ?
C9 C10 C11 C15 179.86(17) . . . . ?
C10 C11 C12 C7 -0.3(3) . . . . ?
C15 C11 C12 C7 179.98(17) . . . . ?
C8 C7 C12 C11 0.1(3) . . . . ?
C13 C7 C12 C11 -179.64(17) . . . . ?
C8 C7 C13 O5 -4.6(3) . . . . ?
C12 C7 C13 O5 175.19(18) . . . . ?
C8 C7 C13 O4 176.72(18) . . . . ?
C12 C7 C13 O4 -3.5(3) . . . . ?
C10 C9 C14 O7 -0.6(3) . . . . ?
C8 C9 C14 O7 -179.74(18) . . . . ?
C10 C9 C14 O6 178.51(17) . . . . ?
C8 C9 C14 O6 -0.6(3) . . . . ?
C12 C11 C15 O9 -3.5(3) . . . . ?
C10 C11 C15 O9 176.8(2) . . . . ?
C12 C11 C15 O8 176.67(19) . . . . ?
C10 C11 C15 O8 -3.1(3) . . . . ?
C2 C1 O1 C6 175.1(2) . . . 2_657 ?
C4 C3 O2 C2 178.9(3) . . . . ?
C1 C2 O2 C3 -177.9(3) . . . . ?
C6 C5 O3 C4 -177.9(2) . . . . ?
C3 C4 O3 C5 173.8(3) . . . . ?
loop_
_publcif_info_tables.block_id
_publcif_info_tables.reference_item
{96bb4f0b-932c-46f8-9852-dee8b2f3db75} '_publcif_info_datablock.publ_exptl'
{96bb4f0b-932c-46f8-9852-dee8b2f3db75} '_geom_hbond_atom_site_label_D'
{fa82224f-74af-4217-9fcd-18991f0ec280} '_geom_hbond_atom_site_label_D'
loop_
_publcif_info_cif.paper_type
CB
loop_
_publcif_info_datablock.id
_publcif_info_datablock.publ_exptl
_publcif_info_datablock.publ_geom
_publcif_info_datablock.structure
{96bb4f0b-932c-46f8-9852-dee8b2f3db75} y y y
{fa82224f-74af-4217-9fcd-18991f0ec280} y y y
loop_
_publcif_info_exptl_table_extra_item
sin_theta_over_lambda_max
loop_
_publcif_info_exptl_table_header_item
?

_cod_database_fobs_code 2108594
