The crystal structure of the zwitterionic co-crystal of 2,4-dichloro-6-{[(3-hydroxypropyl)ammonio]methyl}phenolate and 2,4-dichlorophenol
Uprety, Bhawna; Arderne, Charmaine; Acta Crystallographica Section E 75 (2019) 1452–1455; doi:10.1107/S2056989019012544

data_2243086
_publ_section_title
;
 The crystal structure of the zwitterionic co-crystal of
 2,4-dichloro-6-{[(3-hydroxypropyl)ammonio]methyl}phenolate and
 2,4-dichlorophenol
;
_journal_coeditor_code           FY2140
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              1452
_journal_page_last               1455
_journal_paper_doi               10.1107/S2056989019012544
_journal_volume                  75
_journal_year                    2019
_chemical_absolute_configuration unk
_chemical_formula_iupac          'C10 H13 Cl2 N O2, C6 H4 Cl2 O'
_chemical_formula_moiety         'C10 H13 Cl2 N O2, C6 H4 Cl2 O'
_chemical_formula_sum            'C16 H17 Cl4 N O3'
_chemical_formula_weight         413.10
_chemical_name_systematic
;
2,4-Dichlorophenol--
2,4-dichloro-6-{[(3-hydroxypropyl)ammonio]methyl}phenolate (1/1)
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 101.076(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   26.406(2)
_cell_length_b                   9.5558(9)
_cell_length_c                   7.1019(6)
_cell_measurement_reflns_used    6679
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.558
_cell_measurement_theta_min      2.272
_cell_volume                     1758.6(3)
_computing_cell_refinement
;
SAINT (Bruker, 2016)
;
_computing_data_collection
;
APEX2 (Bruker, 2014)
;
_computing_data_reduction
;
SAINT (Bruker, 2016)
;
_computing_molecular_graphics
;
<i>OLEX2</i> (Dolomanov <i>et al.</i>,  2009)
;
_computing_publication_material
;
<i>OLEX2</i> (Dolomanov <i>et al.</i>,  2009)
;
_computing_structure_refinement
;
ShelXL (Sheldrick, 2015a)
;
_computing_structure_solution
;
<i>SHELXT2014/5</i> (Sheldrick, 2015b)
;
_diffrn_ambient_temperature      99.99
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0534
_diffrn_reflns_av_unetI/netI     0.0513
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            15694
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.558
_diffrn_reflns_theta_min         1.572
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.688
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6877
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2016)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.560
_exptl_crystal_description       plank
_exptl_crystal_F_000             848
_exptl_crystal_size_max          0.389
_exptl_crystal_size_mid          0.196
_exptl_crystal_size_min          0.171
_refine_diff_density_max         0.519
_refine_diff_density_min         -0.255
_refine_ls_abs_structure_details
;
 Refined as an inversion twin
;
_refine_ls_abs_structure_Flack   0.03(8)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         4227
_refine_ls_number_restraints     4
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0413
_refine_ls_R_factor_gt           0.0368
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0510P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0897
_refine_ls_wR_factor_ref         0.0917
_reflns_number_gt                3842
_reflns_number_total             4227
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            fy2140sup1.cif
_cod_data_source_block           I
_cod_database_code               2243086
_cod_database_fobs_code          2243086
_shelx_estimated_absorpt_t_min   0.776
_shelx_estimated_absorpt_t_max   0.891
_shelx_hkl_checksum              39026
_shelx_res_checksum              13277