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#$Date: 2025-08-21 03:19:08 +0300 (Thu, 21 Aug 2025) $
#$Revision: 301842 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/50/25/4502536.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_4502536
loop_
_publ_author_name
'Clarke, Heather D.'
'Arora, Kapildev K.'
'Bass, Heather'
'Kavuru, Padmini'
'Ong, Tien Teng'
'Pujari, Twarita'
'Wojtas, Lukasz'
'Zaworotko, Michael J.'
_publ_section_title
;
 Structure−Stability Relationships in Cocrystal Hydrates: Does the
 Promiscuity of Water Make Crystalline Hydrates the Nemesis of Crystal
 Engineering?
;
_journal_issue                   5
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              2152
_journal_paper_doi               10.1021/cg901345u
_journal_volume                  10
_journal_year                    2010
_chemical_formula_moiety         'C14 H6 O8, C8 H10 N4 O2, H2 O'
_chemical_formula_sum            'C22 H18 N4 O11'
_chemical_formula_weight         514.40
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                104.74(3)
_cell_angle_beta                 95.68(3)
_cell_angle_gamma                113.80(3)
_cell_formula_units_Z            2
_cell_length_a                   9.705(3)
_cell_length_b                   10.926(5)
_cell_length_c                   11.469(7)
_cell_measurement_temperature    100(2)
_cell_volume                     1047.8(9)
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_collection       'SMART (Bruker, 2002)'
_computing_data_reduction        'SAINT (Bruker, 2002)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.916
_diffrn_measured_fraction_theta_max 0.916
_diffrn_measurement_device_type  'BRUKER SMART APEXII CCD'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0739
_diffrn_reflns_av_sigmaI/netI    0.0884
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            9029
_diffrn_reflns_theta_full        65.36
_diffrn_reflns_theta_max         65.36
_diffrn_reflns_theta_min         4.09
_exptl_absorpt_coefficient_mu    1.150
_exptl_absorpt_correction_T_max  0.9447
_exptl_absorpt_correction_T_min  0.9447
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS; (Sheldrick, 2003)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.630
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             532
_exptl_crystal_size_max          0.05
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.704
_refine_diff_density_min         -0.260
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     349
_refine_ls_number_reflns         3301
_refine_ls_number_restraints     8
_refine_ls_restrained_S_all      1.014
_refine_ls_R_factor_all          0.0846
_refine_ls_R_factor_gt           0.0549
_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)+(0.0703P)²+0.3937P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1380
_refine_ls_wR_factor_ref         0.1543
_reflns_number_gt                2354
_reflns_number_total             3301
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            cg901345u_si_003.cif
_cod_data_source_block           ELACAF
_cod_original_cell_volume        1047.9(9)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               4502536
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
C1 C 0.7531(4) 0.2960(3) 0.2639(3) 0.0286(7) Uani 1 1 d .
H1A H 0.6453 0.2516 0.2280 0.034 Uiso 1 1 calc R
C2 C 0.8541(4) 0.2704(3) 0.1957(3) 0.0279(7) Uani 1 1 d .
C3 C 1.2939(4) 0.5853(4) 0.5390(3) 0.0319(8) Uani 1 1 d .
C4 C 1.0698(4) 0.4229(3) 0.3711(3) 0.0272(7) Uani 1 1 d .
C5 C 1.0146(4) 0.3315(3) 0.2490(3) 0.0271(7) Uani 1 1 d .
C6 C 0.9700(4) 0.4523(3) 0.4380(3) 0.0251(7) Uani 1 1 d .
C7 C 0.8099(4) 0.3869(3) 0.3853(3) 0.0276(7) Uani 1 1 d .
C8 C -0.0708(4) 0.0675(3) 0.8594(3) 0.0369(8) Uani 1 1 d U
H8A H -0.1666 0.0674 0.8704 0.044 Uiso 1 1 calc R
C9 C 0.4117(4) 0.1126(3) 0.8801(3) 0.0308(8) Uani 1 1 d .
C10 C 0.3882(4) 0.2361(4) 1.0802(3) 0.0436(9) Uani 1 1 d .
H10A H 0.3970 0.1741 1.1260 0.065 Uiso 1 1 calc R
H10B H 0.3219 0.2777 1.1133 0.065 Uiso 1 1 calc R
H10C H 0.4911 0.3117 1.0892 0.065 Uiso 1 1 calc R
C11 C 0.4541(4) 0.0178(4) 0.6754(3) 0.0390(9) Uani 1 1 d .
H11A H 0.5543 0.1019 0.7022 0.058 Uiso 1 1 calc R
H11B H 0.4095 -0.0016 0.5884 0.058 Uiso 1 1 calc R
H11C H 0.4685 -0.0633 0.6845 0.058 Uiso 1 1 calc R
C12 C 0.1920(4) -0.0078(3) 0.6931(3) 0.0263(7) Uani 1 1 d .
C13 C 0.1662(4) 0.1095(3) 0.8967(3) 0.0259(7) Uani 1 1 d .
C14 C 0.1038(4) 0.0282(3) 0.7734(3) 0.0254(7) Uani 1 1 d .
C15 C 0.2841(3) 0.5594(3) 0.0812(3) 0.0232(7) Uani 1 1 d .
C16 C -0.2178(3) 0.5809(3) 0.1430(3) 0.0251(7) Uani 1 1 d .
H16A H -0.3198 0.5726 0.1364 0.030 Uiso 1 1 calc R
C17 C -0.1752(3) 0.5178(3) 0.0397(3) 0.0221(7) Uani 1 1 d .
C18 C 0.0455(3) 0.6747(3) 0.2669(3) 0.0224(7) Uani 1 1 d .
C19 C -0.1092(3) 0.6561(3) 0.2557(3) 0.0233(7) Uani 1 1 d .
C20 C -0.0229(3) 0.5322(3) 0.0513(3) 0.0198(6) Uani 1 1 d .
C21 C 0.0857(3) 0.6108(3) 0.1641(3) 0.0200(6) Uani 1 1 d .
N1 N 0.3203(3) 0.1538(3) 0.9488(2) 0.0289(6) Uani 1 1 d .
N2 N 0.3486(3) 0.0426(3) 0.7524(2) 0.0291(6) Uani 1 1 d .
N3 N -0.0509(3) -0.0010(3) 0.7481(3) 0.0357(6) Uani 1 1 d U
N4 N 0.0613(3) 0.1360(3) 0.9531(2) 0.0324(7) Uani 1 1 d .
O1 O 1.2286(2) 0.4872(2) 0.42090(19) 0.0324(6) Uani 1 1 d .
O2 O 1.1161(3) 0.3073(2) 0.1862(2) 0.0357(6) Uani 1 1 d .
H2 H 1.0695 0.2545 0.1133 0.054 Uiso 1 1 calc R
O3 O 1.4352(3) 0.6434(3) 0.5695(2) 0.0431(6) Uani 1 1 d .
O4 O 0.8074(3) 0.1845(2) 0.07602(19) 0.0345(6) Uani 1 1 d .
H4 H 0.7292 0.1875 0.0408 0.052 Uiso 1 1 calc R
O5 O 0.1412(3) -0.0750(2) 0.5818(2) 0.0409(6) Uani 1 1 d .
O6 O 0.5451(3) 0.1375(2) 0.9260(2) 0.0390(6) Uani 1 1 d .
O7 O -0.1383(2) 0.7180(2) 0.36187(18) 0.0305(5) Uani 1 1 d .
H7 H -0.2335 0.6946 0.3519 0.046 Uiso 1 1 calc R
O8 O 0.1552(2) 0.7515(2) 0.37323(18) 0.0274(5) Uani 1 1 d .
H8 H 0.1192 0.7908 0.4262 0.041 Uiso 1 1 calc R
O9 O 0.4154(2) 0.5728(2) 0.10742(19) 0.0315(5) Uani 1 1 d .
O10 O 0.2351(2) 0.6238(2) 0.17734(17) 0.0245(5) Uani 1 1 d .
O1W O 0.5779(3) 0.6789(3) 0.3602(2) 0.0440(7) Uani 1 1 d D
H1W H 0.530(5) 0.651(5) 0.415(3) 0.078(16) Uiso 1 1 d D
H2W H 0.509(4) 0.642(5) 0.288(3) 0.082(16) Uiso 1 1 d D
C22 C -0.1729(4) -0.0917(4) 0.6375(3) 0.0474(10) Uani 1 1 d .
H22A H -0.1975 -0.1907 0.6268 0.071 Uiso 1 1 calc R
H22B H -0.1382 -0.0681 0.5653 0.071 Uiso 1 1 calc R
H22C H -0.2653 -0.0774 0.6459 0.071 Uiso 1 1 calc R
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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_3
C2 C1 C7 119.7(3) .
C2 C1 H1A 120.2 .
C7 C1 H1A 120.2 .
O4 C2 C1 123.0(3) .
O4 C2 C5 115.9(3) .
C1 C2 C5 121.0(3) .
O3 C3 O1 116.1(3) .
O3 C3 C7 125.7(3) 2_766
O1 C3 C7 118.1(3) 2_766
C6 C4 O1 121.3(3) .
C6 C4 C5 120.6(3) .
O1 C4 C5 118.0(3) .
O2 C5 C4 118.8(3) .
O2 C5 C2 122.7(3) .
C4 C5 C2 118.5(3) .
C4 C6 C7 120.4(3) .
C4 C6 C6 119.4(4) 2_766
C7 C6 C6 120.2(3) 2_766
C1 C7 C6 119.8(3) .
C1 C7 C3 121.2(3) 2_766
C6 C7 C3 119.0(3) 2_766
N4 C8 N3 113.8(3) .
N4 C8 H8A 123.1 .
N3 C8 H8A 123.1 .
O6 C9 N1 122.6(3) .
O6 C9 N2 120.3(3) .
N1 C9 N2 117.0(3) .
N1 C10 H10A 109.5 .
N1 C10 H10B 109.5 .
H10A C10 H10B 109.5 .
N1 C10 H10C 109.5 .
H10A C10 H10C 109.5 .
H10B C10 H10C 109.5 .
N2 C11 H11A 109.5 .
N2 C11 H11B 109.5 .
H11A C11 H11B 109.5 .
N2 C11 H11C 109.5 .
H11A C11 H11C 109.5 .
H11B C11 H11C 109.5 .
O5 C12 C14 124.5(3) .
O5 C12 N2 122.2(3) .
C14 C12 N2 113.3(3) .
N4 C13 C14 112.2(3) .
N4 C13 N1 127.3(3) .
C14 C13 N1 120.5(3) .
C13 C14 N3 107.6(3) .
C13 C14 C12 123.0(3) .
N3 C14 C12 129.4(3) .
O9 C15 O10 115.5(3) .
O9 C15 C17 126.7(3) 2_565
O10 C15 C17 117.8(2) 2_565
C19 C16 C17 119.4(3) .
C19 C16 H16A 120.3 .
C17 C16 H16A 120.3 .
C16 C17 C20 119.4(3) .
C16 C17 C15 121.4(3) 2_565
C20 C17 C15 119.2(3) 2_565
O8 C18 C21 118.6(3) .
O8 C18 C19 123.0(3) .
C21 C18 C19 118.5(3) .
O7 C19 C16 124.6(3) .
O7 C19 C18 114.0(3) .
C16 C19 C18 121.4(3) .
C21 C20 C17 120.5(3) .
C21 C20 C20 118.8(3) 2_565
C17 C20 C20 120.6(3) 2_565
C18 C21 O10 118.1(2) .
C18 C21 C20 120.7(3) .
O10 C21 C20 121.1(3) .
C9 N1 C13 120.5(3) .
C9 N1 C10 117.7(3) .
C13 N1 C10 121.7(3) .
C9 N2 C12 125.0(3) .
C9 N2 C11 117.1(3) .
C12 N2 C11 117.9(3) .
C8 N3 C14 103.7(3) .
C8 N3 C22 125.5(3) .
C14 N3 C22 130.6(3) .
C13 N4 C8 102.8(3) .
C3 O1 C4 121.7(2) .
C5 O2 H2 109.5 .
C2 O4 H4 109.5 .
C19 O7 H7 109.5 .
C18 O8 H8 109.5 .
C15 O10 C21 122.3(2) .
H1W O1W H2W 109(4) .
N3 C22 H22A 109.5 .
N3 C22 H22B 109.5 .
H22A C22 H22B 109.5 .
N3 C22 H22C 109.5 .
H22A C22 H22C 109.5 .
H22B C22 H22C 109.5 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.384(5) .
C1 C7 1.390(4) .
C1 H1A 0.9500 .
C2 O4 1.359(4) .
C2 C5 1.417(5) .
C3 O3 1.223(4) .
C3 O1 1.389(4) .
C3 C7 1.466(4) 2_766
C4 C6 1.378(4) .
C4 O1 1.394(4) .
C4 C5 1.398(4) .
C5 O2 1.347(4) .
C6 C7 1.410(5) .
C6 C6 1.429(6) 2_766
C7 C3 1.466(4) 2_766
C8 N4 1.380(5) .
C8 N3 1.380(4) .
C8 H8A 0.9500 .
C9 O6 1.239(4) .
C9 N1 1.375(4) .
C9 N2 1.407(4) .
C10 N1 1.466(4) .
C10 H10A 0.9800 .
C10 H10B 0.9800 .
C10 H10C 0.9800 .
C11 N2 1.477(4) .
C11 H11A 0.9800 .
C11 H11B 0.9800 .
C11 H11C 0.9800 .
C12 O5 1.232(4) .
C12 C14 1.406(4) .
C12 N2 1.416(4) .
C13 N4 1.346(4) .
C13 C14 1.383(4) .
C13 N1 1.385(4) .
C14 N3 1.386(4) .
C15 O9 1.219(3) .
C15 O10 1.384(4) .
C15 C17 1.466(4) 2_565
C16 C19 1.396(4) .
C16 C17 1.400(4) .
C16 H16A 0.9500 .
C17 C20 1.410(4) .
C17 C15 1.466(4) 2_565
C18 O8 1.351(4) .
C18 C21 1.386(4) .
C18 C19 1.419(4) .
C19 O7 1.350(3) .
C20 C21 1.399(4) .
C20 C20 1.418(6) 2_565
C21 O10 1.387(3) .
N3 C22 1.452(5) .
O2 H2 0.8400 .
O4 H4 0.8400 .
O7 H7 0.8400 .
O8 H8 0.8400 .
O1W H1W 0.865(19) .
O1W H2W 0.90(2) .
C22 H22A 0.9800 .
C22 H22B 0.9800 .
C22 H22C 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
O2 H2 N4 0.84 1.93 2.702(4) 151.7 1_654
O2 H2 O4 0.84 2.30 2.742(3) 113.3 .
O4 H4 O6 0.84 1.90 2.708(3) 161.3 1_554
O7 H7 O1W 0.84 1.78 2.608(3) 167.2 1_455
O8 H8 O5 0.84 1.93 2.701(3) 152.4 1_565
O8 H8 O7 0.84 2.27 2.706(3) 112.6 .
O1W H1W O3 0.865(19) 2.08(2) 2.920(4) 164(4) 1_455
O1W H2W O9 0.90(2) 1.99(2) 2.854(4) 162(4) .
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139144959
