#------------------------------------------------------------------------------
#$Date: 2022-05-03 11:32:04 +0300 (Tue, 03 May 2022) $
#$Revision: 274841 $
#$URL: file:///home/coder/svn-repositories/cod/cif/8/10/51/8105111.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_8105111
loop_
_publ_author_name
'Liu, Yingfan'
'Li, Xiaochuan'
'Sun, Saisai'
'Ji, Guangqian'
'Son, Young-A.'
_publ_section_title
;
 Crystal structure of
 2,7-diiodo-1,3,6,8-tetramethyl-bis(difluoroboron)-1,2-bis((1H-pyrrol-2-yl)methylene)hydrazine,
 C14H14B2F4I2N4
;
_journal_issue                   2
_journal_name_full
'Zeitschrift für Kristallographie - New Crystal Structures'
_journal_page_first              371
_journal_page_last               372
_journal_paper_doi               10.1515/ncrs-2019-0678
_journal_volume                  235
_journal_year                    2020
_chemical_formula_moiety         'C14 H14 B2 F4 I2 N4'
_chemical_formula_sum            'C14 H14 B2 F4 I2 N4'
_chemical_formula_weight         589.71
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_cell_angle_alpha                108.189(6)
_cell_angle_beta                 110.492(7)
_cell_angle_gamma                98.678(7)
_cell_formula_units_Z            1
_cell_length_a                   7.5458(7)
_cell_length_b                   8.5659(6)
_cell_length_c                   8.6089(5)
_cell_measurement_reflns_used    1531
_cell_measurement_temperature    296.45(11)
_cell_measurement_theta_max      27.5490
_cell_measurement_theta_min      4.4650
_cell_volume                     473.56(8)
_computing_cell_refinement
'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015) [1]'
_computing_data_collection
'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015) [1]'
_computing_data_reduction
'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015) [1]'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009) [2]'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009) [2]'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015) [3]'
_computing_structure_solution    'ShelXT (Sheldrick, 2015) [4]'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      296.45(11)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0528
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
--------------------------------------------------------------------------
  1  ω      1.00  91.00   1.00    5.00    --   21.82  38.00 -30.00   90
  2  ω     46.00  81.00   1.00    5.00    --   21.82  57.00   0.00   35
  3  ω      1.00  91.00   1.00    5.00    --   21.82  57.00-150.00   90
  4  ω     39.00  74.00   1.00    5.00    --   21.82-112.00 -50.00   35
  5  ω    -47.00  48.00   1.00    5.00    --   21.82 -57.00  60.00   95
  6  ω    -63.00 -37.00   1.00    5.00    --  -22.83 112.00  42.00   26
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0386281000
_diffrn_orient_matrix_UB_12      -0.0892624000
_diffrn_orient_matrix_UB_13      -0.0546564000
_diffrn_orient_matrix_UB_21      -0.0975222000
_diffrn_orient_matrix_UB_22      0.0061804000
_diffrn_orient_matrix_UB_23      -0.0196735000
_diffrn_orient_matrix_UB_31      -0.0028544000
_diffrn_orient_matrix_UB_32      0.0173453000
_diffrn_orient_matrix_UB_33      -0.0760585000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0419
_diffrn_reflns_av_unetI/netI     0.0416
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            2991
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.497
_diffrn_reflns_theta_min         3.365
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    3.363
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.45609
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    2.068
_exptl_crystal_description       block
_exptl_crystal_F_000             278
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.6
_exptl_crystal_size_min          0.4
_refine_diff_density_max         0.749
_refine_diff_density_min         -0.547
_refine_diff_density_rms         0.098
_refine_ls_extinction_coef       0.049(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     121
_refine_ls_number_reflns         1960
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.074
_refine_ls_R_factor_all          0.0375
_refine_ls_R_factor_gt           0.0334
_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)+(0.0371P)²+0.2700P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0808
_refine_ls_wR_factor_ref         0.0831
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1785
_reflns_number_total             1960
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            suppl_ncrs-2019-0678_suppl.cif
_cod_data_source_block           20170629sss
_cod_original_cell_volume        473.56(7)
_cod_database_code               8105111
_chemical_oxdiff_formula         'C1 H1 F1 B1 N1 I1'
_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.
;
_reflns_odcompleteness_completeness 99.74
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C7(H7)
2.b Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C5(H5A,H5B,H5C)
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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
B1 B 0.4114(8) 0.2653(5) 0.7872(6) 0.0379(10) Uani 1 1 d . . . . .
C1 C 0.2518(5) 0.2664(5) 0.4677(5) 0.0338(8) Uani 1 1 d . . . . .
C2 C 0.2067(6) 0.3913(5) 0.3997(5) 0.0355(8) Uani 1 1 d . . . . .
C3 C 0.2655(6) 0.5488(5) 0.5418(5) 0.0343(8) Uani 1 1 d . . . . .
C4 C 0.3492(5) 0.5170(5) 0.6987(5) 0.0315(8) Uani 1 1 d . . . . .
C5 C 0.2141(8) 0.0795(6) 0.3670(6) 0.0493(11) Uani 1 1 d . . . . .
H5A H 0.3171 0.0409 0.4330 0.074 Uiso 1 1 calc GR . . . .
H5B H 0.2122 0.0603 0.2504 0.074 Uiso 1 1 calc GR . . . .
H5C H 0.0888 0.0169 0.3528 0.074 Uiso 1 1 calc GR . . . .
C6 C 0.2426(7) 0.7148(5) 0.5322(6) 0.0457(10) Uani 1 1 d . . . . .
H6A H 0.3278 0.7551 0.4835 0.069 Uiso 1 1 calc GR . . . .
H6B H 0.2773 0.7976 0.6510 0.069 Uiso 1 1 calc GR . . . .
H6C H 0.1077 0.6992 0.4558 0.069 Uiso 1 1 calc GR . . . .
C7 C 0.4281(5) 0.6256(4) 0.8775(5) 0.0312(8) Uani 1 1 d . . . . .
H7 H 0.4302 0.7397 0.9022 0.037 Uiso 1 1 calc R . . . .
F1 F 0.2618(5) 0.1442(4) 0.7743(4) 0.0785(10) Uani 1 1 d . . . . .
F2 F 0.5609(5) 0.1966(4) 0.7722(4) 0.0695(9) Uani 1 1 d . . . . .
I1 I 0.06425(4) 0.34161(4) 0.12839(3) 0.05323(18) Uani 1 1 d . . . . .
N1 N 0.3391(5) 0.3433(4) 0.6490(4) 0.0320(7) Uani 1 1 d . . . . .
N2 N 0.5007(4) 0.5852(4) 1.0166(4) 0.0288(6) 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'
B B 0.0013 0.0007 '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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 '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
N2 N2 B1 124.3(4) 2_667 2_667
C7 N2 N2 117.8(4) . 2_667
C7 N2 B1 117.9(3) . 2_667
C1 N1 C4 108.3(3) . .
C1 N1 B1 129.3(3) . .
C4 N1 B1 122.3(3) . .
C1 C2 I1 124.3(3) . .
C3 C2 I1 126.2(3) . .
C3 C2 C1 109.5(3) . .
N2 C7 H7 116.6 . .
N2 C7 C4 126.8(3) . .
C4 C7 H7 116.6 . .
N1 C1 C2 108.1(3) . .
N1 C1 C5 123.1(3) . .
C2 C1 C5 128.8(4) . .
N1 C4 C3 109.0(3) . .
C7 C4 N1 120.5(3) . .
C7 C4 C3 130.4(3) . .
C2 C3 C4 105.1(3) . .
C2 C3 C6 127.8(4) . .
C4 C3 C6 127.1(4) . .
C3 C6 H6A 109.5 . .
C3 C6 H6B 109.5 . .
C3 C6 H6C 109.5 . .
H6A C6 H6B 109.5 . .
H6A C6 H6C 109.5 . .
H6B C6 H6C 109.5 . .
C1 C5 H5A 109.5 . .
C1 C5 H5B 109.5 . .
C1 C5 H5C 109.5 . .
H5A C5 H5B 109.5 . .
H5A C5 H5C 109.5 . .
H5B C5 H5C 109.5 . .
F2 B1 N2 107.4(3) . 2_667
F2 B1 N1 111.4(3) . .
F1 B1 F2 110.1(4) . .
F1 B1 N2 107.7(3) . 2_667
F1 B1 N1 111.9(4) . .
N1 B1 N2 108.2(3) . 2_667
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
I1 C2 2.068(4) .
F2 B1 1.375(5) .
F1 B1 1.360(6) .
N2 N2 1.395(5) 2_667
N2 C7 1.308(5) .
N2 B1 1.594(5) 2_667
N1 C1 1.346(5) .
N1 C4 1.395(4) .
N1 B1 1.521(5) .
C2 C1 1.401(5) .
C2 C3 1.387(6) .
C7 H7 0.9300 .
C7 C4 1.373(5) .
C1 C5 1.490(5) .
C4 C3 1.407(5) .
C3 C6 1.482(5) .
C6 H6A 0.9600 .
C6 H6B 0.9600 .
C6 H6C 0.9600 .
C5 H5A 0.9600 .
C5 H5B 0.9600 .
C5 H5C 0.9600 .
B1 N2 1.594(5) 2_667
