Stoichiometric and polymorphic salts of hexa-methyl-ene-tetra-minium and 2-chloro-4-nitro-benzoate.
Lemmerer, Andreas; Motlaung, Xolani; Acta crystallographica. Section E, Crystallographic communications 73 (2017) 1630–1635; doi:10.1107/S2056989017014359

data_2311463
_publ_section_title
;
 Stoichiometric and polymorphic salts of hexa-methyl-ene-tetra-minium and
 2-chloro-4-nitro-benzoate.
;
_journal_issue                   'Pt 11'
_journal_name_full
'Acta crystallographica. Section E, Crystallographic communications'
_journal_page_first              1630
_journal_page_last               1635
_journal_paper_doi               10.1107/S2056989017014359
_journal_volume                  73
_journal_year                    2017
_chemical_formula_iupac          'C6 H13 N4 +, C7 H3 Cl N O4 -'
_chemical_formula_moiety         'C6 H13 N4 +, C7 H3 Cl N O4 -'
_chemical_formula_sum            'C13 H16 Cl N5 O4'
_chemical_formula_weight         341.76
_chemical_name_systematic
;
Hexamethylenetetraminium 2-chloro-4-nitro-benzoate
;
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'C -2yc'
_symmetry_space_group_name_H-M   'C 1 c 1'
_atom_sites_solution_hydrogens   mixed
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 103.4450(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.90490(10)
_cell_length_b                   21.9330(4)
_cell_length_c                   12.0194(2)
_cell_measurement_reflns_used    8081
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      28.2
_cell_measurement_theta_min      2.55
_cell_volume                     1514.00(5)
_computing_cell_refinement
;
SAINT-Plus (Bruker, 2016)
;
_computing_data_collection
;
APEX3 (Bruker, 2016)
;
_computing_data_reduction
;
SAINT-Plus and XPREP (Bruker 2016)
;
_computing_molecular_graphics
;
Ortep-III for Windows (Farrugia, 2012) and DIAMOND (Brandenburg &
Berndt,
1999)
;
_computing_publication_material
;
WinGX publication routines (Farrugia, 2012)
;
_computing_structure_refinement
;
<i>SHELXL2017/1</i> (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2015)
;
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 1
_diffrn_measurement_device_type  'Bruker D8 Venture Photon CCD area detector'
_diffrn_measurement_method       '\w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0465
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            19814
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.993
_diffrn_reflns_theta_min         1.857
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.282
_exptl_absorpt_correction_T_max  0.9775
_exptl_absorpt_correction_T_min  0.9144
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details
;
(XPREP; Bruker, 2016)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.499
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             712
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.153
_refine_diff_density_min         -0.16
_refine_ls_abs_structure_details
;
Flack <i>x</i> determined using 1663 quotients
[(<i>I</i>^+^)-(<i>I</i>^-^)]/[(<i>I</i>^+^)+(<i>I</i>^-^)]
(Parsons <i>et al.</i>,  2013)
;
_refine_ls_abs_structure_Flack   -0.010(19)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     212
_refine_ls_number_reflns         3644
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.067
_refine_ls_R_factor_all          0.0269
_refine_ls_R_factor_gt           0.0256
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0432P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0651
_refine_ls_wR_factor_ref         0.0659
_reflns_number_gt                3487
_reflns_number_total             3644
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            eb2001sup1.cif
_cod_data_source_block           IIIa
_cod_original_sg_symbol_H-M      'C c'
_cod_database_code               2311463
_shelx_estimated_absorpt_t_min   0.889
_shelx_estimated_absorpt_t_max   0.956
_shelx_hkl_checksum              47721
_shelx_res_checksum              81698