#------------------------------------------------------------------------------
#$Date: 2019-11-23 07:44:51 +0200 (Sat, 23 Nov 2019) $
#$Revision: 232465 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/18/2021827.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2021827
loop_
_publ_author_name
'Rivera, Augusto'
'Rojas, Jicli José'
'Sadat-Bernal, John'
'Ríos-Motta, Jaime'
'Bolte, Michael'
_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          'C7 H14 N4, 2C6 H5 N O3'
_chemical_formula_moiety         'C7 H14 N4, 2(C6 H5 N O3)'
_chemical_formula_sum            'C19 H24 N6 O6'
_chemical_formula_weight         432.44
_chemical_name_systematic
;
3-Nitrophenol--1,3,6,8-tetraazatricyclo[4.3.1.1^3,8^]undecane (2:1)
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           8
_space_group_name_Hall           'C -2y'
_space_group_name_H-M_alt        'C 1 m 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_method           SHELXL-2016/6
_cell_angle_alpha                90
_cell_angle_beta                 120.939(6)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   7.2053(7)
_cell_length_b                   25.253(2)
_cell_length_c                   6.5134(6)
_cell_measurement_reflns_used    8351
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.83
_cell_measurement_theta_min      3.41
_cell_volume                     1016.52(17)
_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
;
SHELXL2018 (Sheldrick, 2015)
;
_computing_structure_refinement
;
SHELXL2018 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Stoe IPDS II two-circle'
_diffrn_measurement_method       ω
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0359
_diffrn_reflns_av_unetI/netI     0.0345
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            8351
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         27.610
_diffrn_reflns_theta_min         3.394
_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  0.529
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(X-AREA; Stoe & Cie, 2001)
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.413
_exptl_crystal_description       plate
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.080
_refine_diff_density_max         0.167
_refine_diff_density_min         -0.194
_refine_ls_abs_structure_details
;
Flack x determined using 883 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons et al., 2013)
;
_refine_ls_abs_structure_Flack   -1.8(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     149
_refine_ls_number_reflns         2401
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0457
_refine_ls_R_factor_gt           0.0391
_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/[σ²(Fo²)+(0.0567P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0911
_refine_ls_wR_factor_ref         0.0937
_reflns_number_gt                2119
_reflns_number_total             2401
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            sk3740sup1.cif
_cod_data_source_block           2a
_cod_original_sg_symbol_H-M      'C m'
_cod_database_code               2021827
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.976
_shelx_estimated_absorpt_t_max   0.991
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
O O1 0.5286(3) 0.16364(8) 0.7582(3) 0.0347(5) Uani d 1
H H1 0.530(6) 0.1304(15) 0.718(6) 0.042(9) Uiso d 1
O O2 0.5119(4) 0.37561(9) 0.3797(4) 0.0585(7) Uani d 1
O O3 0.5330(4) 0.35709(9) 0.7134(4) 0.0495(6) Uani d 1
N N1 0.5539(4) 0.05764(9) 0.7291(4) 0.0322(5) Uani d 1
N N2 0.8694(6) 0.000000 1.0000(6) 0.0405(8) Uani d 1
N N3 0.5526(6) 0.000000 1.0384(6) 0.0380(8) Uani d 1
N N11 0.5176(4) 0.34371(9) 0.5246(4) 0.0361(6) Uani d 1
C C1 0.7924(5) 0.04855(11) 0.8566(6) 0.0392(7) Uani d 1
H H1A 0.837407 0.047695 0.736394 0.047 Uiso calc 1
H H1B 0.865436 0.079135 0.963243 0.047 Uiso calc 1
C C2 0.4302(6) 0.03087(11) 0.4979(5) 0.0403(7) Uani d 1
H H2A 0.486413 0.042928 0.395508 0.048 Uiso calc 1
H H2B 0.278114 0.042929 0.421294 0.048 Uiso calc 1
C C3 0.4749(5) 0.04851(11) 0.8952(5) 0.0376(7) Uani d 1
H H3A 0.517924 0.079087 1.005633 0.045 Uiso calc 1
H H3B 0.314779 0.047512 0.801087 0.045 Uiso calc 1
C C4 0.7891(8) 0.000000 1.1659(7) 0.0430(10) Uani d 1
H H4A 0.844458 -0.031708 1.269749 0.052 Uiso calc 0.5
H H4B 0.844459 0.031708 1.269750 0.052 Uiso calc 0.5
C C11 0.5156(4) 0.19734(10) 0.5904(4) 0.0246(5) Uani d 1
C C12 0.5266(4) 0.25136(11) 0.6409(4) 0.0258(5) Uani d 1
H H12 0.546383 0.263450 0.788997 0.031 Uiso calc 1
C C13 0.5077(4) 0.28686(10) 0.4689(4) 0.0267(5) Uani d 1
C C14 0.4793(4) 0.27170(11) 0.2496(4) 0.0301(6) Uani d 1
H H14 0.466071 0.297122 0.135315 0.036 Uiso calc 1
C C15 0.4711(4) 0.21778(11) 0.2049(4) 0.0298(5) Uani d 1
H H15 0.453845 0.205983 0.057549 0.036 Uiso calc 1
C C16 0.4876(4) 0.18075(10) 0.3706(4) 0.0276(5) Uani d 1
H H16 0.479787 0.144038 0.335216 0.033 Uiso calc 1
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
C11 O1 H1 . . 111(2)
C2 N1 C3 . . 114.9(2)
C2 N1 C1 . . 114.8(2)
C3 N1 C1 . . 109.6(2)
C4 N2 C1 . 2 107.8(2)
C4 N2 C1 . . 107.8(2)
C1 N2 C1 2 . 113.4(3)
C4 N3 C3 . 2 108.3(2)
C4 N3 C3 . . 108.3(2)
C3 N3 C3 2 . 113.5(3)
O3 N11 O2 . . 122.8(3)
O3 N11 C13 . . 119.0(2)
O2 N11 C13 . . 118.2(2)
N2 C1 N1 . . 115.7(2)
N2 C1 H1A . . 108.4
N1 C1 H1A . . 108.4
N2 C1 H1B . . 108.4
N1 C1 H1B . . 108.4
H1A C1 H1B . . 107.4
N1 C2 C2 . 2 117.53(13)
N1 C2 H2A . . 107.9
C2 C2 H2A 2 . 107.9
N1 C2 H2B . . 107.9
C2 C2 H2B 2 . 107.9
H2A C2 H2B . . 107.2
N3 C3 N1 . . 115.6(2)
N3 C3 H3A . . 108.4
N1 C3 H3A . . 108.4
N3 C3 H3B . . 108.4
N1 C3 H3B . . 108.4
H3A C3 H3B . . 107.5
N3 C4 N2 . . 111.6(3)
N3 C4 H4A . . 109.3
N2 C4 H4A . . 109.3
N3 C4 H4B . . 109.3
N2 C4 H4B . . 109.3
H4A C4 H4B . . 108.0
O1 C11 C12 . . 117.0(2)
O1 C11 C16 . . 123.5(2)
C12 C11 C16 . . 119.5(2)
C13 C12 C11 . . 118.1(2)
C13 C12 H12 . . 120.9
C11 C12 H12 . . 120.9
C12 C13 C14 . . 123.7(2)
C12 C13 N11 . . 117.3(2)
C14 C13 N11 . . 119.0(2)
C15 C14 C13 . . 117.0(2)
C15 C14 H14 . . 121.5
C13 C14 H14 . . 121.5
C16 C15 C14 . . 121.4(2)
C16 C15 H15 . . 119.3
C14 C15 H15 . . 119.3
C15 C16 C11 . . 120.2(2)
C15 C16 H16 . . 119.9
C11 C16 H16 . . 119.9
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
O1 C11 . 1.350(3)
O1 H1 . 0.88(4)
O2 N11 . 1.225(3)
O3 N11 . 1.224(3)
N1 C2 . 1.463(4)
N1 C3 . 1.477(3)
N1 C1 . 1.493(4)
N2 C4 . 1.465(5)
N2 C1 2 1.466(3)
N2 C1 . 1.466(3)
N3 C4 . 1.462(6)
N3 C3 2 1.465(3)
N3 C3 . 1.465(3)
N11 C13 . 1.474(3)
C1 H1A . 0.9900
C1 H1B . 0.9900
C2 C2 2 1.559(6)
C2 H2A . 0.9900
C2 H2B . 0.9900
C3 H3A . 0.9900
C3 H3B . 0.9900
C4 H4A . 0.9900
C4 H4B . 0.9900
C11 C12 . 1.396(3)
C11 C16 . 1.403(3)
C12 C13 . 1.386(3)
C12 H12 . 0.9500
C13 C14 . 1.388(4)
C14 C15 . 1.387(4)
C14 H14 . 0.9500
C15 C16 . 1.386(4)
C15 H15 . 0.9500
C16 H16 . 0.9500
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
O1 H1 N1 . 0.88(4) 1.84(4) 2.696(3) 162(3)
C4 H4A O2 3_546 0.99 2.56 3.476(3) 154
C4 H4B O2 4_556 0.99 2.56 3.476(3) 154
C15 H15 O1 1_554 0.95 2.51 3.427(3) 161
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
_geom_torsion
C4 N2 C1 N1 . . -54.3(3)
C1 N2 C1 N1 2 . 65.0(4)
C2 N1 C1 N2 . . -84.3(3)
C3 N1 C1 N2 . . 46.9(3)
C3 N1 C2 C2 . 2 -64.1(2)
C1 N1 C2 C2 . 2 64.4(2)
C4 N3 C3 N1 . . 54.7(3)
C3 N3 C3 N1 2 . -65.6(4)
C2 N1 C3 N3 . . 84.2(3)
C1 N1 C3 N3 . . -46.8(3)
C3 N3 C4 N2 2 . 61.73(19)
C3 N3 C4 N2 . . -61.73(19)
C1 N2 C4 N3 2 . -61.4(2)
C1 N2 C4 N3 . . 61.4(2)
O1 C11 C12 C13 . . -178.3(2)
C16 C11 C12 C13 . . 0.4(3)
C11 C12 C13 C14 . . -0.2(4)
C11 C12 C13 N11 . . 179.4(2)
O3 N11 C13 C12 . . -2.9(3)
O2 N11 C13 C12 . . 176.5(3)
O3 N11 C13 C14 . . 176.8(3)
O2 N11 C13 C14 . . -3.9(4)
C12 C13 C14 C15 . . -0.4(4)
N11 C13 C14 C15 . . 180.0(2)
C13 C14 C15 C16 . . 0.9(4)
C14 C15 C16 C11 . . -0.7(4)
O1 C11 C16 C15 . . 178.6(3)
C12 C11 C16 C15 . . 0.1(3)

_cod_database_fobs_code 2021827
