Crystal structure of 2-phenylethynyl-1,3,6,8-tetramethylBOPHY (BOPHY = bis(difluoroboron)-1,2-bis((1H-pyrrol-2-yl)methylene)hydrazine), C22H20B2F4N4
Liu, Yingfan; Sun, Saisai; Ji, Guangqian; Li, Xiaochuan; Son, Young-A; Zeitschrift für Kristallographie - New Crystal Structures 236 (2021) 749–752; doi:10.1515/ncrs-2021-0074

data_8104700
_publ_section_title
;
 Crystal structure of 2-phenylethynyl-1,3,6,8-tetramethylBOPHY (BOPHY =
 bis(difluoroboron)-1,2-bis((1H-pyrrol-2-yl)methylene)hydrazine),
 C22H20B2F4N4
;
_journal_issue                   4
_journal_name_full
'Zeitschrift f\"ur Kristallographie - New Crystal Structures'
_journal_page_first              749
_journal_page_last               752
_journal_paper_doi               10.1515/ncrs-2021-0074
_journal_volume                  236
_journal_year                    2021
_chemical_formula_moiety         'C22 H20 B2 F4 N4'
_chemical_formula_sum            'C22 H20 B2 F4 N4'
_chemical_formula_weight         438.04
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   9.2506(2)
_cell_length_b                   36.1677(13)
_cell_length_c                   12.9475(3)
_cell_measurement_reflns_used    5136
_cell_measurement_temperature    294.43(10)
_cell_measurement_theta_max      72.0320
_cell_measurement_theta_min      4.1780
_cell_volume                     4331.9(2)
_computing_cell_refinement       'CrysAlisPro 1.171.39.29c (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.29c (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.29c (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      294.43(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0528
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
--------------------------------------------------------------------------
  1  \w    -53.00 -27.00   1.00    1.00    --  -36.07 128.00 123.00   26
  2  \w     -8.00  19.00   1.00    1.00    --   36.07 -19.00 -30.00   27
  3  \w     23.00  50.00   1.00    1.00    --   36.07  77.00-180.00   27
  4  \w     37.00  64.00   1.00    1.00    --   36.07  57.00 -30.00   27
  5  \w    -31.00  27.00   1.00    1.00    --   36.07 -57.00-120.00   58
  6  \w     40.00  65.00   1.00    1.00    --   36.07 -19.00 -30.00   25
  7  \w     25.00  91.00   1.00    1.00    --   36.07  77.00   0.00   66
  8  \w     59.00 101.00   1.00    1.00    --   36.07  77.00-180.00   42
  9  \w     24.00  85.00   1.00    1.00    --   36.07-125.00  90.00   61
 10  \w     60.00 140.00   1.00    2.78    --  109.31 178.00   0.00   80
 11  \w     41.00 106.00   1.00    2.78    --  109.31 -95.00   0.00   65
 12  \w     40.00 127.00   1.00    2.78    --  109.31 -30.00 120.00   87
 13  \w     50.00 127.00   1.00    2.78    --  109.31 -61.00  60.00   77
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0117526000
_diffrn_orient_matrix_UB_12      -0.0410918000
_diffrn_orient_matrix_UB_13      -0.0301959000
_diffrn_orient_matrix_UB_21      -0.1659150000
_diffrn_orient_matrix_UB_22      0.0034810000
_diffrn_orient_matrix_UB_23      -0.0041404000
_diffrn_orient_matrix_UB_31      0.0088869000
_diffrn_orient_matrix_UB_32      0.0106217000
_diffrn_orient_matrix_UB_33      -0.1150321000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0267
_diffrn_reflns_av_unetI/netI     0.0277
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       42
_diffrn_reflns_limit_k_min       -36
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            10648
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        65.969
_diffrn_reflns_theta_max         65.969
_diffrn_reflns_theta_min         4.200
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.879
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61185
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.39.29c (Rigaku Oxford Diffraction, 2017)
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    1.343
_exptl_crystal_description       plate
_exptl_crystal_F_000             1808
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.462
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.140
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     324
_refine_ls_number_reflns         3763
_refine_ls_number_restraints     73
_refine_ls_restrained_S_all      1.131
_refine_ls_R_factor_all          0.0805
_refine_ls_R_factor_gt           0.0729
_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^)+(0.0769P)^2^+6.5468P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1949
_refine_ls_wR_factor_ref         0.1992
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3240
_reflns_number_total             3763
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            suppl_j_ncrs-2021-0074_suppl.cif
_cod_data_source_block           2
_cod_database_code               8104700
_chemical_oxdiff_formula         'C1 H1 F1 B1 N1 '
_reflns_odcompleteness_completeness 99.70
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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. Restrained distances
 C17A-C16 \\sim C17-C16
 with sigma of 0.02
3. Rigid body (RIGU) restrains
 C19A, C17A, C22A, C20A, C18A, C21A
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C17, C20, C19, C18, C21, C22
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
4. Others
 Sof(C17A)=Sof(C18A)=Sof(H18A)=Sof(C19A)=Sof(H19A)=Sof(C20A)=Sof(H20A)=
 Sof(C21A)=Sof(H21A)=Sof(C22A)=Sof(H22A)=1-FVAR(1)
 Sof(C17)=Sof(C22)=Sof(H22)=Sof(C21)=Sof(H21)=Sof(C20)=Sof(H20)=Sof(C19)=
 Sof(H19)=Sof(C18)=Sof(H18)=FVAR(1)
5.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C1(H1), C4(H4), C22(H22), C21(H21), C20(H20), C19(H19), C18(H18),
 C18A(H18A), C19A(H19A), C20A(H20A), C21A(H21A), C22A(H22A)
5.b Fitted hexagon refined as free rotating group:
 C17(C22,C21,C20,C19,C18), C17A(C18A,C19A,C20A,C21A,C22A)
5.c Idealised Me refined as rotating group:
 C12(H12a,H12b,H12c), C11(H11a,H11b,H11c), C14(H14a,H14b,H14c), C13(H13a,H13b,
 H13c)
;