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_2021826
_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          '2C6 H5 N O3, C6 H12 N4, H2 O'
_chemical_formula_moiety         '2(C6 H5 N O3), C6 H12 N4, H2 O'
_chemical_formula_sum            'C18 H24 N6 O7'
_chemical_formula_weight         436.43
_chemical_name_systematic
;
3-Nitrophenol--1,3,5,7-tetraazatricyclo[3.3.1.1^3,7^]decane--water (2:1:1)
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_method           SHELXL-2018/3
_cell_angle_alpha                90
_cell_angle_beta                 104.395(5)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.6765(6)
_cell_length_b                   28.819(3)
_cell_length_c                   6.8163(4)
_cell_measurement_reflns_used    8615
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.48
_cell_measurement_theta_min      2.42
_cell_volume                     2031.4(3)
_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
;
SHELXL2018 (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 0.994
_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  0.0300
_diffrn_reflns_av_unetI/netI     0.0331
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       34
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            8615
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.014
_diffrn_reflns_theta_min         2.424
_diffrn_source                   'Genix 3D I\mS microfocus X-ray source'
_exptl_absorpt_coefficient_mu    0.112
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.678
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(X-AREA; Stoe & Cie, 2001)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.427
_exptl_crystal_description       block
_exptl_crystal_F_000             920
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.230
_refine_diff_density_max         0.191
_refine_diff_density_min         -0.190
_refine_ls_extinction_coef       0.0076(14)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method
;
SHELXL2018 (Sheldrick, 2015)
;
_refine_ls_goodness_of_fit_ref   1.238
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     297
_refine_ls_number_reflns         3559
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.238
_refine_ls_R_factor_all          0.0686
_refine_ls_R_factor_gt           0.0568
_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^)+(0.0402P)^2^+1.5429P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1307
_refine_ls_wR_factor_ref         0.1360
_reflns_number_gt                3024
_reflns_number_total             3559
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            sk3740sup1.cif
_cod_data_source_block           1a
_cod_original_cell_volume        2031.5(2)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2021826
_cod_database_fobs_code          2021826
_shelx_estimated_absorpt_t_min   0.972
_shelx_estimated_absorpt_t_max   0.975
_shelx_hkl_checksum              59474
_shelx_res_checksum              42435