#------------------------------------------------------------------------------
#$Date: 2016-03-21 13:13:48 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178694 $
#$URL: svn://www.crystallography.net/cod/cif/4/08/05/4080541.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_4080541
loop_
_publ_author_name
'Mahdi, Tayseer'
'del Castillo, Jon Nathaniel'
'Stephan, Douglas W.'
_publ_section_title
;
 Metal-Free Hydrogenation ofN-Based Heterocycles
;
_journal_issue                   6
_journal_name_full               Organometallics
_journal_page_first              1971
_journal_paper_doi               10.1021/om4000727
_journal_volume                  32
_journal_year                    2013
_chemical_formula_sum            'C42 H20 B1.33 F20 N1.33'
_chemical_formula_weight         937.67
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 109.317(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            3
_cell_length_a                   13.7416(4)
_cell_length_b                   11.9983(4)
_cell_length_c                   19.1036(7)
_cell_measurement_temperature    150(2)
_cell_volume                     2972.40(17)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0246
_diffrn_reflns_av_sigmaI/netI    0.0235
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            22132
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.22
_exptl_absorpt_coefficient_mu    0.157
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6918
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_density_diffrn    1.572
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1404
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.391
_refine_diff_density_min         -0.240
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     448
_refine_ls_number_reflns         5227
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0481
_refine_ls_R_factor_gt           0.0362
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0553P)²+1.3595P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0970
_refine_ls_wR_factor_ref         0.1054
_reflns_number_gt                4252
_reflns_number_total             5227
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om4000727_si_003.cif
_cod_data_source_block           tm070_0m
_cod_original_sg_symbol_H-M      P2(1)/n
_cod_database_code               4080541
loop_
_symmetry_equiv_pos_as_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.91275(8) 0.79029(9) 0.30114(7) 0.0305(3) Uani 1 1 d . . .
F2 F 1.05366(11) 0.95057(10) 0.33896(8) 0.0473(4) Uani 1 1 d . . .
F3 F 1.24900(10) 0.91216(11) 0.33693(8) 0.0519(4) Uani 1 1 d . . .
F4 F 1.29708(9) 0.70681(12) 0.29803(8) 0.0466(4) Uani 1 1 d . . .
F5 F 1.15907(8) 0.54705(10) 0.25889(7) 0.0320(3) Uani 1 1 d . . .
F6 F 0.99484(7) 0.58892(9) 0.12581(6) 0.0246(3) Uani 1 1 d . . .
F7 F 0.89542(9) 0.68019(11) -0.00565(6) 0.0369(3) Uani 1 1 d . . .
F8 F 0.70893(10) 0.77977(12) -0.03057(7) 0.0458(4) Uani 1 1 d . . .
F9 F 0.62300(8) 0.78137(11) 0.07899(7) 0.0385(3) Uani 1 1 d . . .
F10 F 0.71864(8) 0.69213(9) 0.20893(6) 0.0283(3) Uani 1 1 d . . .
F11 F 1.01152(8) 0.62550(10) 0.41628(6) 0.0281(3) Uani 1 1 d . . .
F12 F 0.91305(9) 0.60590(11) 0.51181(6) 0.0385(3) Uani 1 1 d . . .
F13 F 0.71940(10) 0.51968(12) 0.47098(7) 0.0486(4) Uani 1 1 d . . .
F14 F 0.62547(8) 0.45451(11) 0.32758(7) 0.0392(3) Uani 1 1 d . . .
F15 F 0.72114(8) 0.47738(9) 0.22867(6) 0.0279(3) Uani 1 1 d . . .
N1 N 0.97557(11) 0.44518(12) 0.24427(8) 0.0179(3) Uani 1 1 d . . .
H1B H 1.0232 0.4559 0.2198 0.021 Uiso 1 1 calc R . .
C1 C 1.02728(13) 0.65909(15) 0.27944(10) 0.0204(4) Uani 1 1 d . . .
C2 C 1.00776(14) 0.76615(16) 0.29916(11) 0.0240(4) Uani 1 1 d . . .
C3 C 1.07894(16) 0.85055(16) 0.31865(11) 0.0310(5) Uani 1 1 d . . .
C4 C 1.17718(16) 0.83152(18) 0.31807(11) 0.0332(5) Uani 1 1 d . . .
C5 C 1.20119(14) 0.72795(18) 0.29842(11) 0.0305(5) Uani 1 1 d . . .
C6 C 1.12707(14) 0.64566(16) 0.27913(10) 0.0237(4) Uani 1 1 d . . .
C7 C 0.85822(13) 0.62409(15) 0.17252(10) 0.0188(4) Uani 1 1 d . . .
C8 C 0.89924(13) 0.63098(15) 0.11502(10) 0.0213(4) Uani 1 1 d . . .
C9 C 0.85142(15) 0.68019(17) 0.04756(10) 0.0265(4) Uani 1 1 d . . .
C10 C 0.75692(16) 0.73016(17) 0.03448(11) 0.0293(5) Uani 1 1 d . . .
C11 C 0.71426(14) 0.73072(16) 0.09007(11) 0.0273(4) Uani 1 1 d . . .
C12 C 0.76499(13) 0.68035(15) 0.15703(10) 0.0213(4) Uani 1 1 d . . .
C13 C 0.87074(13) 0.55675(14) 0.31501(10) 0.0186(4) Uani 1 1 d . . .
C14 C 0.91457(13) 0.58550(15) 0.38929(10) 0.0217(4) Uani 1 1 d . . .
C15 C 0.86529(15) 0.57495(17) 0.44131(10) 0.0269(4) Uani 1 1 d . . .
C16 C 0.76764(15) 0.53130(17) 0.42078(12) 0.0304(5) Uani 1 1 d . . .
C17 C 0.72091(14) 0.49836(16) 0.34881(12) 0.0270(4) Uani 1 1 d . . .
C18 C 0.77266(13) 0.51150(15) 0.29846(10) 0.0216(4) Uani 1 1 d . . .
C19 C 1.03679(14) 0.40675(16) 0.32192(10) 0.0235(4) Uani 1 1 d . . .
H15A H 1.0818 0.4685 0.3484 0.028 Uiso 1 1 calc R . .
H15B H 0.9884 0.3893 0.3489 0.028 Uiso 1 1 calc R . .
C20 C 1.10277(15) 0.30542(16) 0.32323(11) 0.0281(4) Uani 1 1 d . . .
H8A H 1.1512 0.3214 0.2959 0.034 Uiso 1 1 calc R . .
H8B H 1.1437 0.2865 0.3751 0.034 Uiso 1 1 calc R . .
C21 C 1.03396(16) 0.20865(16) 0.28750(12) 0.0320(5) Uani 1 1 d . . .
H10A H 0.9897 0.1885 0.3172 0.038 Uiso 1 1 calc R . .
H10B H 1.0766 0.1430 0.2854 0.038 Uiso 1 1 calc R . .
C22 C 0.96724(15) 0.24167(16) 0.20954(12) 0.0288(4) Uani 1 1 d . . .
H12A H 0.9185 0.1801 0.1883 0.035 Uiso 1 1 calc R . .
H12B H 1.0123 0.2496 0.1787 0.035 Uiso 1 1 calc R . .
C23 C 0.90494(13) 0.34991(15) 0.20334(11) 0.0221(4) Uani 1 1 d . . .
H20A H 0.8517 0.3374 0.2277 0.027 Uiso 1 1 calc R . .
C24 C 0.84958(14) 0.37244(15) 0.12161(11) 0.0238(4) Uani 1 1 d . . .
C25 C 0.90407(16) 0.38098(16) 0.07166(11) 0.0284(4) Uani 1 1 d . . .
H4A H 0.9772 0.3763 0.0895 0.034 Uiso 1 1 calc R . .
C26 C 0.85332(18) 0.39605(18) -0.00308(12) 0.0359(5) Uani 1 1 d . . .
H6A H 0.8916 0.4037 -0.0361 0.043 Uiso 1 1 calc R . .
C27 C 0.74708(19) 0.39998(19) -0.03010(13) 0.0419(6) Uani 1 1 d . . .
H2A H 0.7121 0.4116 -0.0815 0.050 Uiso 1 1 calc R . .
C28 C 0.69193(17) 0.38698(19) 0.01787(13) 0.0404(5) Uani 1 1 d . . .
H1A H 0.6187 0.3875 -0.0008 0.048 Uiso 1 1 calc R . .
C29 C 0.74235(15) 0.37313(17) 0.09302(12) 0.0305(5) Uani 1 1 d . . .
H16A H 0.7034 0.3640 0.1255 0.037 Uiso 1 1 calc R . .
C30 C 0.3943(3) 0.4104(5) 0.3767(2) 0.1250(19) Uani 1 1 d . . .
C31 C 0.4313(4) 0.4944(6) 0.4252(3) 0.0529(14) Uani 0.50 1 d P A 1
C32 C 0.5000 0.5000 0.5000 0.0871(18) Uani 1 2 d S . .
C33 C 0.4643(5) 0.4206(6) 0.4504(4) 0.0575(14) Uani 0.50 1 d P A 2
B1 B 0.92884(15) 0.57068(17) 0.25246(11) 0.0185(4) 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'
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
C19 N1 C23 108.95(14) . .
C19 N1 B1 106.85(13) . .
C23 N1 B1 121.51(13) . .
C6 C1 C2 112.93(17) . .
C6 C1 B1 129.14(17) . .
C2 C1 B1 117.64(15) . .
F1 C2 C3 116.33(17) . .
F1 C2 C1 118.76(16) . .
C3 C2 C1 124.89(18) . .
F2 C3 C2 120.62(19) . .
F2 C3 C4 120.03(18) . .
C2 C3 C4 119.34(19) . .
F3 C4 C5 120.31(19) . .
F3 C4 C3 121.0(2) . .
C5 C4 C3 118.68(18) . .
F4 C5 C4 119.88(18) . .
F4 C5 C6 120.15(19) . .
C4 C5 C6 119.97(18) . .
F5 C6 C5 114.76(16) . .
F5 C6 C1 121.08(16) . .
C5 C6 C1 124.16(18) . .
C12 C7 C8 112.83(16) . .
C12 C7 B1 127.30(15) . .
C8 C7 B1 119.14(15) . .
F6 C8 C9 116.20(15) . .
F6 C8 C7 118.80(16) . .
C9 C8 C7 124.98(17) . .
F7 C9 C8 121.01(17) . .
F7 C9 C10 119.76(17) . .
C8 C9 C10 119.23(17) . .
F8 C10 C11 120.72(17) . .
F8 C10 C9 120.53(18) . .
C11 C10 C9 118.73(18) . .
F9 C11 C10 119.66(17) . .
F9 C11 C12 120.21(17) . .
C10 C11 C12 120.13(17) . .
F10 C12 C11 114.76(15) . .
F10 C12 C7 121.28(16) . .
C11 C12 C7 123.93(17) . .
C18 C13 C14 112.94(16) . .
C18 C13 B1 122.68(16) . .
C14 C13 B1 124.35(15) . .
F11 C14 C15 114.54(17) . .
F11 C14 C13 121.26(15) . .
C15 C14 C13 124.20(17) . .
F12 C15 C16 120.03(17) . .
F12 C15 C14 120.25(17) . .
C16 C15 C14 119.71(18) . .
F13 C16 C17 120.62(18) . .
F13 C16 C15 120.24(19) . .
C17 C16 C15 119.13(17) . .
F14 C17 C16 120.15(16) . .
F14 C17 C18 120.65(18) . .
C16 C17 C18 119.20(17) . .
F15 C18 C17 115.51(16) . .
F15 C18 C13 119.72(15) . .
C17 C18 C13 124.77(17) . .
C20 C19 N1 113.37(15) . .
C21 C20 C19 109.17(16) . .
C20 C21 C22 109.08(16) . .
C21 C22 C23 115.80(17) . .
C24 C23 N1 114.11(15) . .
C24 C23 C22 107.84(15) . .
N1 C23 C22 110.32(14) . .
C29 C24 C25 117.92(19) . .
C29 C24 C23 120.67(17) . .
C25 C24 C23 121.05(17) . .
C26 C25 C24 121.00(19) . .
C25 C26 C27 120.2(2) . .
C28 C27 C26 119.6(2) . .
C27 C28 C29 120.5(2) . .
C28 C29 C24 120.7(2) . .
C31 C30 C33 43.9(3) . .
C30 C31 C32 134.0(6) . .
C33 C32 C33 180.000(2) 3_666 .
C33 C32 C31 135.9(3) 3_666 .
C33 C32 C31 44.1(3) . .
C33 C32 C31 44.1(3) 3_666 3_666
C33 C32 C31 135.9(3) . 3_666
C31 C32 C31 180.000(2) . 3_666
C32 C33 C30 137.9(6) . .
C7 B1 C13 115.70(14) . .
C7 B1 C1 102.07(14) . .
C13 B1 C1 112.29(15) . .
C7 B1 N1 113.13(14) . .
C13 B1 N1 105.69(14) . .
C1 B1 N1 107.87(13) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
F1 C2 1.350(2) .
F2 C3 1.342(2) .
F3 C4 1.343(2) .
F4 C5 1.344(2) .
F5 C6 1.362(2) .
F6 C8 1.358(2) .
F7 C9 1.344(2) .
F8 C10 1.338(2) .
F9 C11 1.346(2) .
F10 C12 1.351(2) .
F11 C14 1.348(2) .
F12 C15 1.341(2) .
F13 C16 1.341(2) .
F14 C17 1.345(2) .
F15 C18 1.350(2) .
N1 C19 1.515(2) .
N1 C23 1.536(2) .
N1 B1 1.665(2) .
C1 C6 1.383(2) .
C1 C2 1.390(3) .
C1 B1 1.661(3) .
C2 C3 1.371(3) .
C3 C4 1.373(3) .
C4 C5 1.370(3) .
C5 C6 1.378(3) .
C7 C12 1.390(2) .
C7 C8 1.393(2) .
C7 B1 1.644(3) .
C8 C9 1.371(3) .
C9 C10 1.376(3) .
C10 C11 1.372(3) .
C11 C12 1.378(3) .
C13 C18 1.389(2) .
C13 C14 1.389(3) .
C13 B1 1.651(3) .
C14 C15 1.381(3) .
C15 C16 1.371(3) .
C16 C17 1.369(3) .
C17 C18 1.381(3) .
C19 C20 1.512(3) .
C20 C21 1.510(3) .
C21 C22 1.521(3) .
C22 C23 1.538(3) .
C23 C24 1.518(3) .
C24 C29 1.392(3) .
C24 C25 1.398(3) .
C25 C26 1.378(3) .
C26 C27 1.379(3) .
C27 C28 1.378(3) .
C28 C29 1.382(3) .
C30 C31 1.350(7) .
C30 C33 1.423(7) .
C31 C32 1.431(6) .
C32 C33 1.319(6) 3_666
C32 C33 1.319(6) .
C32 C31 1.431(6) 3_666
