#------------------------------------------------------------------------------
#$Date: 2022-09-16 11:29:00 +0200 (Fri 16 de Sep de 2022) $
#$Revision: 277920 $
#$URL: svn://www.crystallography.net/cod/cif/8/10/57/8105785.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_8105785
loop_
_publ_author_name
'Said, A. Musa'
'Warad, Ismail'
'Alzahrani, O. Seraj'
'Zarrouk, Abdelkader'
'Lentz, Dieter'
_publ_section_title
;
 Crystal structure of
 4,4-dimethyl-2-(trifluoromethyl)-4,5-dihydro-1H-imidazole, C6H9F3N2
;
_journal_issue                   3
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              579
_journal_page_last               580
_journal_paper_doi               10.1515/ncrs-2018-0582
_journal_volume                  234
_journal_year                    2019
_chemical_formula_sum            'C6 H9 F3 N2 O0'
_chemical_formula_weight         166.15
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   mixed
_cell_angle_alpha                90
_cell_angle_beta                 105.903(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   10.6224(9)
_cell_length_b                   11.8639(9)
_cell_length_c                   13.3139(11)
_cell_measurement_reflns_used    9985
_cell_measurement_temperature    102(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.87
_cell_volume                     1613.6(2)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX3'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_temperature      102(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker D8 Venture Photon'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0292
_diffrn_reflns_av_unetI/netI     0.0186
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            25043
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.577
_diffrn_reflns_theta_min         2.183
_diffrn_source                   'Incoatec Microfocus Source'
_exptl_absorpt_coefficient_mu    0.133
_exptl_absorpt_correction_T_max  0.80
_exptl_absorpt_correction_T_min  0.76
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2016/2 (Bruker AXS)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.368
_exptl_crystal_description       block
_exptl_crystal_F_000             688
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
_refine_diff_density_max         0.816
_refine_diff_density_min         -0.840
_refine_diff_density_rms         0.066
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     211
_refine_ls_number_reflns         3722
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0729
_refine_ls_R_factor_gt           0.0618
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0694P)²+2.1236P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1531
_refine_ls_wR_factor_ref         0.1629
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3126
_reflns_number_total             3722
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2018-0582_suppl.cif
_cod_data_source_block           1
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               8105785
_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   0.949
_shelx_estimated_absorpt_t_max   0.976
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.6367(2) 0.27964(17) 0.58791(15) 0.0254(4) Uani 1 1 d . . . . .
C2 C 0.73966(18) 0.44033(16) 0.63748(15) 0.0220(4) Uani 1 1 d . . . . .
C3 C 0.6742(2) 0.40100(18) 0.72269(16) 0.0281(4) Uani 1 1 d . . . . .
H3A H 0.739069 0.395447 0.791899 0.034 Uiso 1 1 calc R U . . .
H3B H 0.603163 0.452885 0.727600 0.034 Uiso 1 1 calc R U . . .
C4 C 0.5809(3) 0.1758(2) 0.52623(18) 0.0413(6) Uani 1 1 d . . . . .
C5 C 0.6921(2) 0.55617(19) 0.59481(18) 0.0333(5) Uani 1 1 d . . . . .
H5A H 0.729385 0.574908 0.537231 0.050 Uiso 1 1 calc R U . . .
H5B H 0.719890 0.612439 0.650379 0.050 Uiso 1 1 calc R U . . .
H5C H 0.596356 0.555871 0.569313 0.050 Uiso 1 1 calc R U . . .
C6 C 0.8882(2) 0.4379(2) 0.67844(19) 0.0346(5) Uani 1 1 d . . . . .
H6A H 0.916767 0.361909 0.703466 0.052 Uiso 1 1 calc R U . . .
H6B H 0.916464 0.491723 0.736064 0.052 Uiso 1 1 calc R U . . .
H6C H 0.927006 0.458485 0.622156 0.052 Uiso 1 1 calc R U . . .
C7 C 0.40653(17) 0.18527(15) 0.85401(14) 0.0181(4) Uani 1 1 d . . . . .
C8 C 0.22696(18) 0.08125(16) 0.77486(14) 0.0214(4) Uani 1 1 d . . . . .
C9 C 0.31326(19) 0.11170(18) 0.70118(15) 0.0241(4) Uani 1 1 d . . . . .
H9A H 0.349257 0.042471 0.678059 0.029 Uiso 1 1 calc R U . . .
H9B H 0.260652 0.152188 0.638705 0.029 Uiso 1 1 calc R U . . .
C10 C 0.49772(19) 0.25035(17) 0.94148(14) 0.0232(4) Uani 1 1 d . . . . .
C11 C 0.0969(2) 0.1437(2) 0.74606(18) 0.0326(5) Uani 1 1 d . . . . .
H11A H 0.052868 0.132647 0.801053 0.049 Uiso 1 1 calc R U . . .
H11B H 0.041604 0.114349 0.679815 0.049 Uiso 1 1 calc R U . . .
C12 C 0.2065(2) -0.04492(18) 0.78123(18) 0.0350(5) Uani 1 1 d . . . . .
H12A H 0.291734 -0.082610 0.804080 0.053 Uiso 1 1 calc R U . . .
H12B H 0.158469 -0.073403 0.712299 0.053 Uiso 1 1 calc R U . . .
H12C H 0.156267 -0.060202 0.831429 0.053 Uiso 1 1 calc R U . . .
F1 F 0.6175(4) 0.08556(15) 0.57764(17) 0.1328(15) Uani 1 1 d . . . . .
F2 F 0.4514(2) 0.1738(2) 0.5063(2) 0.1104(11) Uani 1 1 d . . . . .
F3 F 0.6078(2) 0.16886(14) 0.43734(13) 0.0660(6) Uani 1 1 d . . . . .
F4 F 0.58725(15) 0.30726(13) 0.90982(10) 0.0436(4) Uani 1 1 d . . . . .
F5 F 0.56104(13) 0.18335(11) 1.01875(10) 0.0353(3) Uani 1 1 d . . . . .
F6 F 0.43133(14) 0.32464(12) 0.98252(11) 0.0413(4) Uani 1 1 d . . . . .
N1 N 0.69927(17) 0.35430(14) 0.55252(13) 0.0246(4) Uani 1 1 d . . . . .
H1N H 0.567(3) 0.259(3) 0.706(2) 0.051(9) Uiso 1 1 d . . . . .
N2 N 0.6232(2) 0.29123(17) 0.68486(15) 0.0371(5) Uani 1 1 d . . . . .
H2N H 0.283(3) 0.137(2) 0.928(2) 0.036(7) Uiso 1 1 d . . . . .
N3 N 0.31069(16) 0.12340(15) 0.87538(13) 0.0252(4) Uani 1 1 d . . . . .
H3N H 0.112590 0.224286 0.738743 0.049 Uiso 1 1 calc R U . . .
N4 N 0.42054(16) 0.18443(13) 0.76162(12) 0.0207(3) Uani 1 1 d . . . . .
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'
F F 0.0171 0.0103 '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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C7 N4 C9 104.62(15) . .
C7 N3 C8 107.19(15) . .
C7 N3 H2N 121.4(19) . .
C8 N3 H2N 123.9(19) . .
C1 N1 C2 105.40(16) . .
C1 N2 C3 107.33(17) . .
C1 N2 H1N 124(2) . .
C3 N2 H1N 123(2) . .
N4 C7 N3 119.51(17) . .
N4 C7 C10 121.84(16) . .
N3 C7 C10 118.61(16) . .
F4 C10 F5 107.22(17) . .
F4 C10 F6 107.41(17) . .
F5 C10 F6 106.87(16) . .
F4 C10 C7 112.36(15) . .
F5 C10 C7 111.95(16) . .
F6 C10 C7 110.76(16) . .
N1 C1 N2 119.23(18) . .
N1 C1 C4 122.28(18) . .
N2 C1 C4 118.46(18) . .
N1 C2 C5 109.71(16) . .
N1 C2 C6 108.20(16) . .
C5 C2 C6 110.91(18) . .
N1 C2 C3 104.70(15) . .
C5 C2 C3 112.00(17) . .
C6 C2 C3 111.07(17) . .
N3 C8 C12 110.06(16) . .
N3 C8 C11 110.09(17) . .
C12 C8 C11 111.14(18) . .
N3 C8 C9 100.37(14) . .
C12 C8 C9 112.43(17) . .
C11 C8 C9 112.26(16) . .
N4 C9 C8 106.94(14) . .
N4 C9 H9A 110.3 . .
C8 C9 H9A 110.3 . .
N4 C9 H9B 110.3 . .
C8 C9 H9B 110.3 . .
H9A C9 H9B 108.6 . .
N2 C3 C2 102.47(15) . .
N2 C3 H3A 111.3 . .
C2 C3 H3A 111.3 . .
N2 C3 H3B 111.3 . .
C2 C3 H3B 111.3 . .
H3A C3 H3B 109.2 . .
C2 C6 H6A 109.5 . .
C2 C6 H6B 109.5 . .
H6A C6 H6B 109.5 . .
C2 C6 H6C 109.5 . .
H6A C6 H6C 109.5 . .
H6B C6 H6C 109.5 . .
C8 C11 H11A 109.5 . .
C8 C11 H11B 109.5 . .
H11A C11 H11B 109.5 . .
C8 C11 H3N 109.5 . .
H11A C11 H3N 109.5 . .
H11B C11 H3N 109.5 . .
C2 C5 H5A 109.5 . .
C2 C5 H5B 109.5 . .
H5A C5 H5B 109.5 . .
C2 C5 H5C 109.5 . .
H5A C5 H5C 109.5 . .
H5B C5 H5C 109.5 . .
C8 C12 H12A 109.5 . .
C8 C12 H12B 109.5 . .
H12A C12 H12B 109.5 . .
C8 C12 H12C 109.5 . .
H12A C12 H12C 109.5 . .
H12B C12 H12C 109.5 . .
F1 C4 F3 109.1(3) . .
F1 C4 F2 103.9(3) . .
F3 C4 F2 107.0(2) . .
F1 C4 C1 112.2(2) . .
F3 C4 C1 113.40(18) . .
F2 C4 C1 110.8(2) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
F5 C10 1.328(2) .
F4 C10 1.326(2) .
F6 C10 1.336(2) .
F3 C4 1.294(3) .
N4 C7 1.279(2) .
N4 C9 1.479(2) .
N3 C7 1.347(2) .
N3 C8 1.476(2) .
N3 H2N 0.85(3) .
N1 C1 1.273(3) .
N1 C2 1.496(2) .
N2 C1 1.344(3) .
N2 C3 1.447(3) .
N2 H1N 0.82(3) .
C7 C10 1.507(3) .
C1 C4 1.509(3) .
C2 C5 1.520(3) .
C2 C6 1.522(3) .
C2 C3 1.556(3) .
C8 C12 1.518(3) .
C8 C11 1.521(3) .
C8 C9 1.558(3) .
F2 C4 1.327(4) .
F1 C4 1.273(3) .
C9 H9A 0.9900 .
C9 H9B 0.9900 .
C3 H3A 0.9900 .
C3 H3B 0.9900 .
C6 H6A 0.9800 .
C6 H6B 0.9800 .
C6 H6C 0.9800 .
C11 H11A 0.9800 .
C11 H11B 0.9800 .
C11 H3N 0.9800 .
C5 H5A 0.9800 .
C5 H5B 0.9800 .
C5 H5C 0.9800 .
C12 H12A 0.9800 .
C12 H12B 0.9800 .
C12 H12C 0.9800 .
