#------------------------------------------------------------------------------
#$Date: 2019-11-24 02:04:13 +0200 (Sun, 24 Nov 2019) $
#$Revision: 236167 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/39/1553922.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_1553922
loop_
_publ_author_name
'Grandl, Markus'
'Sun, Yu'
'Pammer, Frank'
_publ_section_title
;
 Electronic and structural properties of N → B-ladder boranes
 with high electron affinity
;
_journal_issue                   3
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              336
_journal_paper_doi               10.1039/C7QO00876G
_journal_volume                  5
_journal_year                    2018
_chemical_formula_sum            'C50 H29 B2 F20 N3'
_chemical_formula_weight         1073.38
_space_group_crystal_system      monoclinic
_space_group_IT_number           13
_space_group_name_Hall           '-P 2yac'
_space_group_name_H-M_alt        'P 1 2/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2017-09-26 deposited with the CCDC.
2017-11-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 111.844(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   13.3636(3)
_cell_length_b                   12.7650(2)
_cell_length_c                   15.0491(3)
_cell_measurement_reflns_used    4783
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      74.0410
_cell_measurement_theta_min      3.4470
_cell_volume                     2382.85(9)
_computing_cell_refinement       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SIR92 (Giacovazzo et al., 1994)'
_diffrn_ambient_temperature      150(2)
_diffrn_detector_area_resol_mean 10.3385
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0239
_diffrn_reflns_av_unetI/netI     0.0272
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            9545
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         74.117
_diffrn_reflns_theta_min         3.462
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    1.265
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94603
_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            yellow
_exptl_crystal_density_diffrn    1.496
_exptl_crystal_description       'transparent prism'
_exptl_crystal_F_000             1080
_exptl_crystal_size_max          0.164
_exptl_crystal_size_mid          0.149
_exptl_crystal_size_min          0.136
_refine_diff_density_max         0.918
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.090
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     356
_refine_ls_number_reflns         4709
_refine_ls_number_restraints     17
_refine_ls_restrained_S_all      1.104
_refine_ls_R_factor_all          0.0579
_refine_ls_R_factor_gt           0.0510
_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)+(0.1192P)²+0.7405P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1688
_refine_ls_wR_factor_ref         0.1791
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4051
_reflns_number_total             4709
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c7qo00876g2.cif
_cod_data_source_block           shelx_CCDC4
_cod_original_sg_symbol_H-M      'P 2/n'
_cod_database_code               1553922
_shelx_shelxl_version_number     2014/7
_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   0.819
_shelx_estimated_absorpt_t_max   0.847
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, 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
C1 C 0.45569(16) 0.08371(15) 0.66992(13) 0.0212(4) Uani 1 1 d . . .
C2 C 0.35799(16) 0.03209(17) 0.65083(15) 0.0263(4) Uani 1 1 d . . .
H2 H 0.2924 0.0678 0.6169 0.032 Uiso 1 1 calc R U .
C3 C 0.35449(17) -0.07111(18) 0.68053(15) 0.0287(5) Uani 1 1 d . . .
H3 H 0.2869 -0.1047 0.6666 0.034 Uiso 1 1 calc R U .
C4 C 0.44947(17) -0.12502(16) 0.73042(15) 0.0259(4) Uani 1 1 d . . .
H4 H 0.4468 -0.1947 0.7516 0.031 Uiso 1 1 calc R U .
C5 C 0.54762(16) -0.07639(15) 0.74889(14) 0.0230(4) Uani 1 1 d . . .
H5 H 0.6127 -0.1133 0.7817 0.028 Uiso 1 1 calc R U .
C6 C 0.55144(15) 0.02702(15) 0.71949(13) 0.0208(4) Uani 1 1 d . . .
C7 C 0.46109(15) 0.19773(15) 0.64425(13) 0.0207(4) Uani 1 1 d . . .
H7 H 0.3907 0.2298 0.6387 0.025 Uiso 1 1 calc R U .
C8 C 0.47046(17) 0.21134(16) 0.54374(14) 0.0248(4) Uani 1 1 d . . .
H8 H 0.4834 0.2875 0.5364 0.030 Uiso 1 1 calc R U .
C9 C 0.36326(18) 0.1833(2) 0.46434(15) 0.0345(5) Uani 1 1 d . . .
H9A H 0.3670 0.1992 0.4019 0.052 Uiso 1 1 calc R U .
H9B H 0.3052 0.2242 0.4724 0.052 Uiso 1 1 calc R U .
H9C H 0.3488 0.1084 0.4677 0.052 Uiso 1 1 calc R U .
C10 C 0.56059(17) 0.15106(19) 0.52673(15) 0.0311(5) Uani 1 1 d . . .
H10A H 0.5570 0.0770 0.5424 0.047 Uiso 1 1 calc R U .
H10B H 0.6306 0.1800 0.5675 0.047 Uiso 1 1 calc R U .
H10C H 0.5520 0.1576 0.4594 0.047 Uiso 1 1 calc R U .
C11 C 0.52187(15) 0.22429(16) 0.83331(14) 0.0223(4) Uani 1 1 d . . .
C12 C 0.57459(16) 0.16044(16) 0.91101(15) 0.0251(4) Uani 1 1 d . . .
C13 C 0.53780(18) 0.1398(2) 0.98420(15) 0.0322(5) Uani 1 1 d . . .
C14 C 0.44480(19) 0.1866(2) 0.98286(16) 0.0393(6) Uani 1 1 d . . .
C15 C 0.39094(17) 0.2546(2) 0.90940(16) 0.0345(5) Uani 1 1 d . . .
C16 C 0.42930(16) 0.27177(17) 0.83737(14) 0.0264(4) Uani 1 1 d . . .
C17 C 0.57748(16) 0.37589(15) 0.74290(14) 0.0220(4) Uani 1 1 d . . .
C18 C 0.65947(17) 0.41846(16) 0.82236(15) 0.0252(4) Uani 1 1 d . . .
C19 C 0.68449(19) 0.52390(17) 0.83599(17) 0.0323(5) Uani 1 1 d . . .
C20 C 0.6231(2) 0.59390(17) 0.76757(19) 0.0355(5) Uani 1 1 d . . .
C21 C 0.53832(19) 0.55780(18) 0.68945(17) 0.0326(5) Uani 1 1 d . . .
C22 C 0.51640(17) 0.45115(17) 0.67857(15) 0.0263(4) Uani 1 1 d . . .
C23 C 0.65574(15) 0.07773(15) 0.73918(13) 0.0196(4) Uani 1 1 d . . .
C24 C 0.7500 0.2323(2) 0.7500 0.0187(5) Uani 1 2 d S T P
H24 H 0.7500 0.3067 0.7500 0.022 Uiso 1 2 calc R U P
C25 C 0.7500 0.0241(2) 0.7500 0.0212(5) Uani 1 2 d S T P
H25 H 0.7500 -0.0504 0.7500 0.025 Uiso 1 2 calc R U P
N1 N 0.66044(12) 0.18508(12) 0.74621(11) 0.0187(3) Uani 1 1 d . . .
F12 F 0.66880(10) 0.11256(11) 0.92052(9) 0.0301(3) Uani 1 1 d . . .
F13 F 0.59212(12) 0.07456(14) 1.05586(10) 0.0445(4) Uani 1 1 d . . .
F14 F 0.40735(13) 0.16798(19) 1.05232(11) 0.0620(6) Uani 1 1 d . . .
F15 F 0.30209(11) 0.30391(16) 0.90964(11) 0.0493(4) Uani 1 1 d . . .
F16 F 0.37242(10) 0.33875(11) 0.76767(9) 0.0328(3) Uani 1 1 d . . .
F18 F 0.72232(10) 0.35349(10) 0.89203(9) 0.0298(3) Uani 1 1 d . . .
F19 F 0.76635(12) 0.55757(12) 0.91282(11) 0.0444(4) Uani 1 1 d . . .
F20 F 0.64525(14) 0.69654(11) 0.77848(13) 0.0512(4) Uani 1 1 d . . .
F21 F 0.47626(14) 0.62593(11) 0.62455(12) 0.0476(4) Uani 1 1 d . . .
F22 F 0.42884(11) 0.42430(10) 0.60268(9) 0.0346(3) Uani 1 1 d . . .
B1 B 0.55252(17) 0.24976(17) 0.73871(15) 0.0196(4) Uani 1 1 d . . .
C26 C 0.2861(8) 0.5664(9) 0.8993(7) 0.094(3) Uani 0.5 1 d D U P
H26A H 0.3026 0.5051 0.9416 0.141 Uiso 0.5 1 calc R U P
H26B H 0.2265 0.5497 0.8393 0.141 Uiso 0.5 1 calc R U P
H26C H 0.2655 0.6252 0.9308 0.141 Uiso 0.5 1 calc R U P
C27 C 0.3748(8) 0.5931(6) 0.8803(6) 0.085(3) Uani 0.5 1 d D U P
N2 N 0.4436(10) 0.6188(9) 0.8599(10) 0.150(5) Uani 0.5 1 d D U P
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0090 0.0039 '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
C2 C1 C6 117.41(18) . .
C2 C1 C7 122.12(18) . .
C6 C1 C7 120.39(17) . .
C1 C2 C3 121.34(19) . .
C1 C2 H2 119.3 . .
C3 C2 H2 119.3 . .
C4 C3 C2 120.40(19) . .
C4 C3 H3 119.8 . .
C2 C3 H3 119.8 . .
C5 C4 C3 119.52(19) . .
C5 C4 H4 120.2 . .
C3 C4 H4 120.2 . .
C4 C5 C6 120.23(18) . .
C4 C5 H5 119.9 . .
C6 C5 H5 119.9 . .
C5 C6 C1 121.09(18) . .
C5 C6 C23 119.82(17) . .
C1 C6 C23 119.09(17) . .
C1 C7 C8 112.32(16) . .
C1 C7 B1 105.09(15) . .
C8 C7 B1 119.40(16) . .
C1 C7 H7 106.4 . .
C8 C7 H7 106.4 . .
B1 C7 H7 106.4 . .
C9 C8 C10 108.59(17) . .
C9 C8 C7 109.82(17) . .
C10 C8 C7 117.05(17) . .
C9 C8 H8 107.0 . .
C10 C8 H8 107.0 . .
C7 C8 H8 107.0 . .
C8 C9 H9A 109.5 . .
C8 C9 H9B 109.5 . .
H9A C9 H9B 109.5 . .
C8 C9 H9C 109.5 . .
H9A C9 H9C 109.5 . .
H9B C9 H9C 109.5 . .
C8 C10 H10A 109.5 . .
C8 C10 H10B 109.5 . .
H10A C10 H10B 109.5 . .
C8 C10 H10C 109.5 . .
H10A C10 H10C 109.5 . .
H10B C10 H10C 109.5 . .
C12 C11 C16 113.50(18) . .
C12 C11 B1 129.19(17) . .
C16 C11 B1 117.30(17) . .
F12 C12 C11 120.98(17) . .
F12 C12 C13 114.76(18) . .
C11 C12 C13 124.3(2) . .
F13 C13 C14 119.9(2) . .
F13 C13 C12 120.7(2) . .
C14 C13 C12 119.4(2) . .
F14 C14 C13 120.7(2) . .
F14 C14 C15 120.2(2) . .
C13 C14 C15 119.1(2) . .
F15 C15 C16 121.0(2) . .
F15 C15 C14 119.4(2) . .
C16 C15 C14 119.6(2) . .
F16 C16 C15 116.47(19) . .
F16 C16 C11 119.52(18) . .
C15 C16 C11 124.0(2) . .
C22 C17 C18 113.40(18) . .
C22 C17 B1 126.31(18) . .
C18 C17 B1 119.88(17) . .
F18 C18 C19 115.76(19) . .
F18 C18 C17 119.15(18) . .
C19 C18 C17 125.1(2) . .
F19 C19 C20 120.4(2) . .
F19 C19 C18 121.1(2) . .
C20 C19 C18 118.4(2) . .
F20 C20 C21 120.5(2) . .
F20 C20 C19 119.9(2) . .
C21 C20 C19 119.6(2) . .
F21 C21 C20 119.7(2) . .
F21 C21 C22 120.3(2) . .
C20 C21 C22 120.0(2) . .
F22 C22 C21 115.46(19) . .
F22 C22 C17 121.07(19) . .
C21 C22 C17 123.4(2) . .
N1 C23 C25 117.99(17) . .
N1 C23 C6 118.00(16) . .
C25 C23 C6 124.00(18) . .
N1 C24 N1 125.8(2) . 2_656
N1 C24 H24 117.1 . .
N1 C24 H24 117.1 2_656 .
C23 C25 C23 120.9(2) . 2_656
C23 C25 H25 119.5 . .
C23 C25 H25 119.5 2_656 .
C24 N1 C23 118.20(17) . .
C24 N1 B1 122.40(17) . .
C23 N1 B1 119.10(15) . .
N1 B1 C7 102.17(14) . .
N1 B1 C17 109.43(15) . .
C7 B1 C17 120.57(16) . .
N1 B1 C11 109.71(15) . .
C7 B1 C11 108.96(15) . .
C17 B1 C11 105.78(15) . .
C27 C26 H26A 109.5 . .
C27 C26 H26B 109.5 . .
H26A C26 H26B 109.5 . .
C27 C26 H26C 109.5 . .
H26A C26 H26C 109.5 . .
H26B C26 H26C 109.5 . .
N2 C27 C26 175.5(15) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 C2 1.394(3) .
C1 C6 1.417(3) .
C1 C7 1.514(3) .
C2 C3 1.397(3) .
C2 H2 0.9500 .
C3 C4 1.393(3) .
C3 H3 0.9500 .
C4 C5 1.383(3) .
C4 H4 0.9500 .
C5 C6 1.399(3) .
C5 H5 0.9500 .
C6 C23 1.464(3) .
C7 C8 1.573(3) .
C7 B1 1.632(3) .
C7 H7 1.0000 .
C8 C9 1.528(3) .
C8 C10 1.529(3) .
C8 H8 1.0000 .
C9 H9A 0.9800 .
C9 H9B 0.9800 .
C9 H9C 0.9800 .
C10 H10A 0.9800 .
C10 H10B 0.9800 .
C10 H10C 0.9800 .
C11 C12 1.384(3) .
C11 C16 1.399(3) .
C11 B1 1.653(3) .
C12 F12 1.358(2) .
C12 C13 1.388(3) .
C13 F13 1.342(3) .
C13 C14 1.373(3) .
C14 F14 1.338(3) .
C14 C15 1.379(3) .
C15 F15 1.345(3) .
C15 C16 1.378(3) .
C16 F16 1.348(2) .
C17 C22 1.392(3) .
C17 C18 1.397(3) .
C17 B1 1.641(3) .
C18 F18 1.355(2) .
C18 C19 1.384(3) .
C19 F19 1.333(3) .
C19 C20 1.379(3) .
C20 F20 1.340(3) .
C20 C21 1.374(3) .
C21 F21 1.340(3) .
C21 C22 1.389(3) .
C22 F22 1.340(2) .
C23 N1 1.374(2) .
C23 C25 1.389(2) .
C24 N1 1.322(2) .
C24 N1 1.322(2) 2_656
C24 H24 0.9500 .
C25 C23 1.389(2) 2_656
C25 H25 0.9500 .
N1 B1 1.629(2) .
C26 C27 1.362(10) .
C26 H26A 0.9800 .
C26 H26B 0.9800 .
C26 H26C 0.9800 .
C27 N2 1.121(10) .
