#------------------------------------------------------------------------------
#$Date: 2025-08-19 13:01:59 +0300 (Tue, 19 Aug 2025) $
#$Revision: 301802 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/10/80/2108025.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_2108025
loop_
_publ_author_name
'Daszkiewicz, Marek'
'Mielcarek, Agnieszka'
_publ_section_title
;
 Comparison of hydrogen bonds and diverse weak interactions of the nitro
 group in 2-methyl-4-nitroanilinium nitrate, bisulfate and two
 hexafluoridosilicates: elementary graph-set approach
;
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section B'
_journal_page_first              916
_journal_page_last               926
_journal_paper_doi               10.1107/S2052520616016139
_journal_volume                  72
_journal_year                    2016
_chemical_formula_moiety         '2(C7 H9 N2 O2), F6 Si, 2(H2 O'
_chemical_formula_sum            'C14 H22 F6 N4 O6 Si'
_chemical_formula_weight         484.44
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 104.638(5)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   15.0445(8)
_cell_length_b                   8.8682(4)
_cell_length_c                   8.1133(4)
_cell_measurement_reflns_used    1555
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      23.531
_cell_measurement_theta_min      2.689
_cell_volume                     1047.32(9)
_computing_cell_refinement       'CrysAlis 1.171.38.34a'
_computing_data_collection       'CrysAlis 1.171.38.34a'
_computing_data_reduction        'CrysAlis 1.171.38.34a'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2014)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'KUMA KM-4 with area CCD detector'
_diffrn_measurement_method       ω-scan
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0457
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            8200
_diffrn_reflns_theta_full        23.531
_diffrn_reflns_theta_max         23.531
_diffrn_reflns_theta_min         2.689
_exptl_absorpt_coefficient_mu    0.204
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68144
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.34a (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.536
_exptl_crystal_description       plate
_exptl_crystal_F_000             500
_exptl_crystal_size_max          0.319
_exptl_crystal_size_mid          0.292
_exptl_crystal_size_min          0.012
_refine_diff_density_max         0.279
_refine_diff_density_min         -0.243
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     150
_refine_ls_number_reflns         1555
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      1.088
_refine_ls_R_factor_all          0.0764
_refine_ls_R_factor_gt           0.0471
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         <0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0453P)²+0.4536P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1003
_refine_ls_wR_factor_ref         0.1128
_reflns_number_gt                1117
_reflns_number_total             1555
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            eb5052sup1.cif
_cod_data_source_block           1652
_cod_depositor_comments
;

2019-10-27
Z value and formula fixed to values more according to usual
chemical conventions.                 miguel
;
_cod_original_formula_sum        'C7 H11 F3 N2 O3 Si0.50'
_cod_original_formula_units_Z    4
_cod_original_formula_weight     242.22
_cod_database_code               2108025
_cod_database_fobs_code          2108025
_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.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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
Si Si1 0.0000 0.0000 0.5000 0.0362(3) Uani d 1
F F1 0.06765(12) 0.14276(19) 0.5961(2) 0.0531(5) Uani d 1
F F2 -0.00753(12) 0.0786(2) 0.3116(2) 0.0572(6) Uani d 1
F F3 0.09301(12) -0.09649(19) 0.4815(2) 0.0561(5) Uani d 1
C C1 0.22639(19) 0.3269(3) 0.4282(3) 0.0390(7) Uani d 1
N N1 0.13715(16) 0.3805(3) 0.4478(3) 0.0445(7) Uani d 1
H H1A 0.1023 0.4089 0.3468 0.067 Uiso calc 1
H H1B 0.1458 0.4587 0.5189 0.067 Uiso calc 1
H H1C 0.1093 0.3066 0.4894 0.067 Uiso calc 1
C C2 0.2905(2) 0.4294(4) 0.4027(4) 0.0509(9) Uani d 1
C C3 0.3720(2) 0.3692(5) 0.3811(4) 0.0643(11) Uani d 1
H H3 0.4183 0.4333 0.3664 0.077 Uiso calc 1
C C4 0.3847(2) 0.2168(5) 0.3813(4) 0.0571(10) Uani d 1
N N2 0.4714(3) 0.1580(6) 0.3516(5) 0.0897(12) Uani d 1
O O1 0.5362(2) 0.2402(5) 0.3735(6) 0.159(2) Uani d 1
O O2 0.4730(2) 0.0260(5) 0.3111(5) 0.1256(14) Uani d 1
C C5 0.3205(2) 0.1170(4) 0.4047(4) 0.0625(10) Uani d 1
H H5 0.3307 0.0136 0.4042 0.075 Uiso calc 1
C C6 0.2400(2) 0.1739(4) 0.4290(4) 0.0524(9) Uani d 1
H H6 0.1947 0.1088 0.4461 0.063 Uiso calc 1
C C7 0.2733(3) 0.5961(4) 0.3940(6) 0.0899(14) Uani d 1
H H7A 0.2141 0.6161 0.3191 0.135 Uiso calc 1
H H7B 0.3199 0.6453 0.3516 0.135 Uiso calc 1
H H7C 0.2750 0.6335 0.5058 0.135 Uiso calc 1
O O1W 0.1241(3) 0.6204(3) 0.6491(4) 0.0857(10) Uani d 1
H H1W 0.108(3) 0.701(3) 0.603(6) 0.128 Uiso d 1
H H2W 0.111(3) 0.615(6) 0.741(4) 0.128 Uiso d 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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Si Si 0.0817 0.0704 '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
F2 Si1 F2 3_556 . 180.0
F2 Si1 F3 3_556 3_556 89.78(9)
F2 Si1 F3 . 3_556 90.22(9)
F2 Si1 F3 3_556 . 90.22(9)
F2 Si1 F3 . . 89.78(9)
F3 Si1 F3 3_556 . 180.0
F2 Si1 F1 3_556 . 89.81(8)
F2 Si1 F1 . . 90.19(8)
F3 Si1 F1 3_556 . 89.73(9)
F3 Si1 F1 . . 90.27(9)
F2 Si1 F1 3_556 3_556 90.19(8)
F2 Si1 F1 . 3_556 89.81(8)
F3 Si1 F1 3_556 3_556 90.27(9)
F3 Si1 F1 . 3_556 89.73(9)
F1 Si1 F1 . 3_556 180.0
C6 C1 C2 . . 122.9(3)
C6 C1 N1 . . 117.3(3)
C2 C1 N1 . . 119.7(3)
C1 N1 H1A . . 109.5
C1 N1 H1B . . 109.5
H1A N1 H1B . . 109.5
C1 N1 H1C . . 109.5
H1A N1 H1C . . 109.5
H1B N1 H1C . . 109.5
C1 C2 C3 . . 116.0(3)
C1 C2 C7 . . 122.6(3)
C3 C2 C7 . . 121.3(3)
C4 C3 C2 . . 120.6(3)
C4 C3 H3 . . 119.7
C2 C3 H3 . . 119.7
C5 C4 C3 . . 122.7(3)
C5 C4 N2 . . 118.7(4)
C3 C4 N2 . . 118.6(4)
O1 N2 O2 . . 123.8(4)
O1 N2 C4 . . 118.7(5)
O2 N2 C4 . . 117.4(4)
C4 C5 C6 . . 117.7(3)
C4 C5 H5 . . 121.1
C6 C5 H5 . . 121.1
C5 C6 C1 . . 120.0(3)
C5 C6 H6 . . 120.0
C1 C6 H6 . . 120.0
C2 C7 H7A . . 109.5
C2 C7 H7B . . 109.5
H7A C7 H7B . . 109.5
C2 C7 H7C . . 109.5
H7A C7 H7C . . 109.5
H7B C7 H7C . . 109.5
H1W O1W H2W . . 111(5)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
Si1 F2 3_556 1.6577(16)
Si1 F2 . 1.6577(16)
Si1 F3 3_556 1.6789(17)
Si1 F3 . 1.6790(17)
Si1 F1 . 1.6868(16)
Si1 F1 3_556 1.6868(16)
C1 C6 . 1.372(4)
C1 C2 . 1.378(4)
C1 N1 . 1.470(3)
N1 H1A . 0.8900
N1 H1B . 0.8900
N1 H1C . 0.8900
C2 C3 . 1.389(5)
C2 C7 . 1.499(5)
C3 C4 . 1.365(5)
C3 H3 . 0.9300
C4 C5 . 1.359(5)
C4 N2 . 1.480(5)
N2 O1 . 1.193(5)
N2 O2 . 1.217(5)
C5 C6 . 1.371(4)
C5 H5 . 0.9300
C6 H6 . 0.9300
C7 H7A . 0.9600
C7 H7B . 0.9600
C7 H7C . 0.9600
O1W H1W . 0.819(19)
O1W H2W . 0.818(19)
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
N1 H1A F1 4_565 0.89 2.02 2.787(3) 143.6
N1 H1A F2 2 0.89 2.24 3.040(3) 149.2
N1 H1B O1W . 0.89 1.86 2.719(4) 162.0
N1 H1C F1 . 0.89 1.88 2.761(3) 171.7
C3 H3 O2 2_655 0.93 2.57 3.412(5) 150.5
C6 H6 F1 . 0.93 2.53 3.227(4) 132.0
C6 H6 F3 . 0.93 2.44 3.361(4) 170.1
O1W H1W F3 1_565 0.819(19) 2.03(2) 2.837(3) 168(5)
O1W H2W F3 4_566 0.818(19) 2.04(2) 2.859(3) 174(5)
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
C6 C1 C2 C3 -1.4(5)
N1 C1 C2 C3 -178.4(3)
C6 C1 C2 C7 177.1(4)
N1 C1 C2 C7 0.1(5)
C1 C2 C3 C4 1.7(5)
C7 C2 C3 C4 -176.8(4)
C2 C3 C4 C5 -1.0(6)
C2 C3 C4 N2 177.8(3)
C5 C4 N2 O1 -161.4(4)
C3 C4 N2 O1 19.7(6)
C5 C4 N2 O2 16.4(6)
C3 C4 N2 O2 -162.5(4)
C3 C4 C5 C6 0.0(5)
N2 C4 C5 C6 -178.9(3)
C4 C5 C6 C1 0.4(5)
C2 C1 C6 C5 0.4(5)
N1 C1 C6 C5 177.5(3)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139064609
