Mechanochemical synthesis and X-ray structural characterization of three 3-nitrophenol cocrystals with three aminal cage azaadamantanes: the role of the stereoelectronic effect on intermolecular hydrogen-bonding patterns
Rivera, Augusto; Rojas, Jicli José; Sadat-Bernal, John; Ríos-Motta, Jaime; Bolte, Michael; Acta Crystallographica Section C 75 (2019) –; doi:10.1107/S205322961901516X

data_2021828
_publ_section_title
;
 Mechanochemical synthesis and X-ray structural characterization of three
 3-nitrophenol cocrystals with three aminal cage azaadamantanes: the role
 of the stereoelectronic effect on intermolecular hydrogen-bonding
 patterns
;
_journal_coeditor_code           SK3740
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first
;
;
_journal_paper_doi               10.1107/S205322961901516X
_journal_volume                  75
_journal_year                    2019
_chemical_formula_iupac          'C8 H16 N4, 2C6 H5 N O3'
_chemical_formula_moiety         'C8 H16 N4, 2(C6 H5 N O3)'
_chemical_formula_sum            'C20 H26 N6 O6'
_chemical_formula_weight         446.47
_chemical_name_systematic
;
3-Nitrophenol--1,3,6,8-tetraazatricyclo[4.4.1.1^3,8^]dodecane (2:1)
;
_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'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 106.338(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   26.159(3)
_cell_length_b                   6.4931(4)
_cell_length_c                   12.8070(14)
_cell_measurement_reflns_used    11125
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.84
_cell_measurement_theta_min      3.54
_cell_volume                     2087.5(4)
_computing_cell_refinement
;
X-AREA (Stoe & Cie, 2001)
;
_computing_data_collection
;
X-AREA (Stoe & Cie, 2001)
;
_computing_data_reduction
;
X-AREA (Stoe & Cie, 2001)
;
_computing_molecular_graphics
;
XP in SHELXTL-Plus (Sheldrick, 2008)
;
_computing_publication_material  SHELXL
_computing_structure_refinement
;
SHELXL2014 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Stoe IPDS II two-circle'
_diffrn_measurement_method       \w
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0266
_diffrn_reflns_av_unetI/netI     0.0266
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            11125
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.626
_diffrn_reflns_theta_min         3.535
_diffrn_source                   'Genix 3D I\mS microfocus X-ray source'
_exptl_absorpt_coefficient_mu    0.107
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.582
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(X-AREA; Stoe & Cie, 2001)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.421
_exptl_crystal_description       plate
_exptl_crystal_F_000             944
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.090
_refine_diff_density_max         0.144
_refine_diff_density_min         -0.155
_refine_ls_abs_structure_details
;
Flack <i>x</i> determined using 1329 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons <i>et al.</i>, 2013)
;
_refine_ls_abs_structure_Flack   -0.2(9)
_refine_ls_extinction_coef       0.0087(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method
;
SHELXL2014 (Sheldrick, 2015)
;
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     298
_refine_ls_number_reflns         3505
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.082
_refine_ls_R_factor_all          0.0393
_refine_ls_R_factor_gt           0.0362
_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/[\s^2^(Fo^2^)+(0.0416P)^2^+1.2092P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0853
_refine_ls_wR_factor_ref         0.0867
_reflns_number_gt                3297
_reflns_number_total             3505
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            sk3740sup1.cif
_cod_data_source_block           3a
_cod_original_sg_symbol_H-M      'C c'
_cod_database_code               2021828
_cod_database_fobs_code          2021828
_shelx_estimated_absorpt_t_min   0.973
_shelx_estimated_absorpt_t_max   0.990
_shelx_hkl_checksum              86609
_shelx_res_checksum              3915