Hierarchy of Supramolecular Synthons: Persistent Hydrogen Bonds Between Carboxylates and Weakly Acidic Hydroxyl Moieties in Cocrystals of Zwitterions
Kavuru, Padmini; Aboarayes, Dalia; Arora, Kapildev K.; Clarke, Heather D.; Kennedy, Alyssa; Marshall, Lissette; Ong, Tien Teng; Perman, Jason; Pujari, Twarita; Wojtas, Łukasz; Zaworotko, Michael J.; Crystal Growth & Design 10 (2010) 3568–3584; doi:10.1021/cg100484a

data_4510988
_publ_section_title
;
 Hierarchy of Supramolecular Synthons: Persistent Hydrogen Bonds Between
 Carboxylates and Weakly Acidic Hydroxyl Moieties in Cocrystals of
 Zwitterions
;
_journal_coden_ASTM              CGDEFU
_journal_issue                   8
_journal_name_full               'Crystal Growth & Design'
_journal_page_first              3568
_journal_page_last               3584
_journal_paper_doi               10.1021/cg100484a
_journal_volume                  10
_journal_year                    2010
_chemical_formula_moiety         '2(C10 H12 Cl N O2), 2(C10 H10 O4), H2 O'
_chemical_formula_sum            'C20 H23 Cl N O6.5'
_chemical_formula_weight         416.84
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 99.0100(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   18.4101(3)
_cell_length_b                   7.7540(2)
_cell_length_c                   28.1511(5)
_cell_measurement_temperature    100(2)
_cell_volume                     3969.04(14)
_computing_cell_refinement       'SAINT (Bruker, 2008)'
_computing_data_collection       'APEX2 (Bruker, 2008)'
_computing_data_reduction        'SAINT (Bruker, 2008)'
_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 0.982
_diffrn_measured_fraction_theta_max 0.982
_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  0.0673
_diffrn_reflns_av_sigmaI/netI    0.0688
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_number            34705
_diffrn_reflns_theta_full        65.82
_diffrn_reflns_theta_max         65.82
_diffrn_reflns_theta_min         2.69
_exptl_absorpt_coefficient_mu    2.056
_exptl_absorpt_correction_T_max  0.9042
_exptl_absorpt_correction_T_min  0.4262
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2007/4; (Bruker, 2007)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.395
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1752
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.05
_refine_diff_density_max         1.093
_refine_diff_density_min         -0.721
_refine_diff_density_rms         0.130
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.033
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     529
_refine_ls_number_reflns         6870
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0924
_refine_ls_R_factor_gt           0.0799
_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/[\s^2^(Fo^2^)+(0.0562P)^2^+10.7287P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1935
_refine_ls_wR_factor_ref         0.2026
_reflns_number_gt                5640
_reflns_number_total             6870
_reflns_threshold_expression     >2sigma(I)
_cod_duplicate_entry             4501801
_cod_data_source_file            cg100484a_si_010.cif
_cod_data_source_block           FERBAC
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               4510988