#------------------------------------------------------------------------------
#$Date: 2017-05-05 11:53:49 +0300 (Fri, 05 May 2017) $
#$Revision: 196242 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/04/29/7042901.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_7042901
loop_
_publ_author_name
'Bamford, Karlee L.'
'Longobardi, Lauren E.'
'Liu, Lei'
'Grimme, Stefan'
'Stephan, Douglas W.'
_publ_section_title
;
 FLP reduction and hydroboration of phenanthrene o-iminoquinones and
 α-diimines.
;
_journal_issue                   16
_journal_name_full
'Dalton transactions (Cambridge, England : 2003)'
_journal_page_first              5308
_journal_page_last               5319
_journal_paper_doi               10.1039/c7dt01024a
_journal_volume                  46
_journal_year                    2017
_chemical_formula_sum            'C40 H22 B F10 N2'
_chemical_formula_weight         731.40
_space_group_crystal_system      orthorhombic
_space_group_IT_number           60
_space_group_name_Hall           '-P 2n 2ab'
_space_group_name_H-M_alt        'P b c n'
_symmetry_space_group_name_Hall  '-P 2n 2ab'
_symmetry_space_group_name_H-M   'P b c n'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2017-03-28 deposited with the CCDC.
2017-03-28 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.508(4)
_cell_length_b                   21.381(8)
_cell_length_c                   15.841(6)
_cell_measurement_reflns_used    587
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      14.63
_cell_measurement_theta_min      2.57
_cell_volume                     3220(2)
_computing_data_collection       'Bruker APEX2'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1999)'
_computing_publication_material  'ORTEP-3 (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker APEX II CCD'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.2099
_diffrn_reflns_av_unetI/netI     0.1262
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            14156
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        20.000
_diffrn_reflns_theta_max         20.000
_diffrn_reflns_theta_min         1.905
_exptl_absorpt_coefficient_mu    0.129
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.4833
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            violet
_exptl_crystal_density_diffrn    1.509
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1484
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_refine_diff_density_max         0.205
_refine_diff_density_min         -0.255
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     241
_refine_ls_number_reflns         1507
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.056
_refine_ls_R_factor_all          0.1317
_refine_ls_R_factor_gt           0.0578
_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)+(0.0919P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1350
_refine_ls_wR_factor_ref         0.1971
_reflns_Friedel_coverage         0.000
_reflns_number_gt                861
_reflns_number_total             1507
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c7dt01024a2.cif
_cod_data_source_block           compound_18
_cod_database_code               7042901
_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.
;
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -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
B01 B 0.0000 0.1775(6) 0.2500 0.029(4) Uani 1 2 d S T P
N01 N 0.0561(7) 0.2264(3) 0.3163(4) 0.0303(19) Uani 1 1 d . . .
F302 F 0.3036(5) 0.2099(2) 0.2312(3) 0.0496(14) Uani 1 1 d . . .
F303 F 0.4943(7) 0.1438(3) 0.1479(3) 0.0688(17) Uani 1 1 d . . .
F304 F 0.4257(6) 0.0374(3) 0.0665(3) 0.0712(19) Uani 1 1 d . . .
F305 F 0.1561(6) -0.0051(2) 0.0740(3) 0.0708(19) Uani 1 1 d . . .
F306 F -0.0356(6) 0.0552(2) 0.1629(3) 0.0492(15) Uani 1 1 d . . .
C01 C 0.1519(11) 0.1450(4) 0.6572(5) 0.066(3) Uani 1 1 d . . .
H01A H 0.1317 0.1786 0.6976 0.098 Uiso 1 1 calc R U .
H01B H 0.2491 0.1308 0.6648 0.098 Uiso 1 1 calc R U .
H01C H 0.0874 0.1100 0.6670 0.098 Uiso 1 1 calc R U .
C101 C 0.0370(8) 0.2863(4) 0.2892(5) 0.031(2) Uani 1 1 d . . .
C102 C 0.0937(9) 0.3435(4) 0.3227(5) 0.034(2) Uani 1 1 d . . .
C103 C 0.2013(9) 0.3453(4) 0.3844(5) 0.041(2) Uani 1 1 d . . .
H103 H 0.2309 0.3074 0.4102 0.050 Uiso 1 1 calc R U .
C104 C 0.2643(10) 0.4008(5) 0.4079(6) 0.048(3) Uani 1 1 d . . .
H104 H 0.3371 0.4009 0.4490 0.058 Uiso 1 1 calc R U .
C105 C 0.2206(12) 0.4561(5) 0.3711(7) 0.056(3) Uani 1 1 d . . .
H105 H 0.2628 0.4945 0.3876 0.068 Uiso 1 1 calc R U .
C106 C 0.1180(12) 0.4560(4) 0.3117(6) 0.052(3) Uani 1 1 d . . .
H106 H 0.0895 0.4948 0.2881 0.062 Uiso 1 1 calc R U .
C107 C 0.0519(9) 0.4009(4) 0.2836(5) 0.039(2) Uani 1 1 d . . .
C201 C 0.0853(9) 0.2085(4) 0.4015(5) 0.026(2) Uani 1 1 d . . .
C202 C 0.0095(9) 0.2357(4) 0.4669(6) 0.037(2) Uani 1 1 d . . .
H202 H -0.0587 0.2671 0.4559 0.044 Uiso 1 1 calc R U .
C203 C 0.0356(10) 0.2159(4) 0.5485(5) 0.043(3) Uani 1 1 d . . .
H203 H -0.0150 0.2349 0.5934 0.051 Uiso 1 1 calc R U .
C204 C 0.1327(10) 0.1694(4) 0.5676(6) 0.043(3) Uani 1 1 d . . .
C205 C 0.2083(9) 0.1432(4) 0.5016(6) 0.039(2) Uani 1 1 d . . .
H205 H 0.2761 0.1116 0.5127 0.047 Uiso 1 1 calc R U .
C206 C 0.1849(9) 0.1631(4) 0.4191(5) 0.032(2) Uani 1 1 d . . .
H206 H 0.2379 0.1454 0.3743 0.039 Uiso 1 1 calc R U .
C301 C 0.1222(10) 0.1347(4) 0.2032(5) 0.030(2) Uani 1 1 d . . .
C302 C 0.2608(11) 0.1543(4) 0.1946(5) 0.042(2) Uani 1 1 d . . .
C303 C 0.3625(10) 0.1210(5) 0.1510(6) 0.048(3) Uani 1 1 d . . .
C304 C 0.3247(14) 0.0667(5) 0.1111(5) 0.051(3) Uani 1 1 d . . .
C305 C 0.1902(12) 0.0475(5) 0.1149(6) 0.044(3) Uani 1 1 d . . .
C306 C 0.0952(10) 0.0798(4) 0.1606(5) 0.034(2) 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'
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'
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
N01 B01 N01 96.9(9) 4 .
N01 B01 C301 115.3(4) 4 4
N01 B01 C301 107.8(3) . 4
N01 B01 C301 107.8(3) 4 .
N01 B01 C301 115.3(4) . .
C301 B01 C301 112.8(10) 4 .
C101 N01 C201 125.0(6) . .
C101 N01 B01 111.6(6) . .
C201 N01 B01 121.3(6) . .
N01 C101 C101 109.8(4) . 4
N01 C101 C102 129.3(7) . .
C101 C101 C102 120.3(5) 4 .
C103 C102 C107 118.5(8) . .
C103 C102 C101 123.2(8) . .
C107 C102 C101 117.8(8) . .
C104 C103 C102 121.6(9) . .
C103 C104 C105 119.4(9) . .
C106 C105 C104 120.5(9) . .
C105 C106 C107 122.8(10) . .
C106 C107 C102 117.1(8) . .
C106 C107 C107 122.4(6) . 4
C102 C107 C107 120.4(5) . 4
C206 C201 C202 119.8(7) . .
C206 C201 N01 120.6(7) . .
C202 C201 N01 119.5(8) . .
C203 C202 C201 118.5(8) . .
C202 C203 C204 122.8(8) . .
C205 C204 C203 117.9(8) . .
C205 C204 C01 120.1(9) . .
C203 C204 C01 121.9(9) . .
C204 C205 C206 120.0(9) . .
C201 C206 C205 120.9(8) . .
C306 C301 C302 112.7(8) . .
C306 C301 B01 124.1(8) . .
C302 C301 B01 122.9(8) . .
F302 C302 C303 116.4(9) . .
F302 C302 C301 119.8(9) . .
C303 C302 C301 123.7(9) . .
F303 C303 C304 122.3(10) . .
F303 C303 C302 118.8(11) . .
C304 C303 C302 118.9(10) . .
C305 C304 F304 124.1(11) . .
C305 C304 C303 119.1(9) . .
F304 C304 C303 116.7(12) . .
F305 C305 C304 117.7(9) . .
F305 C305 C306 121.9(10) . .
C304 C305 C306 120.4(10) . .
C305 C306 F306 115.6(9) . .
C305 C306 C301 125.1(9) . .
F306 C306 C301 119.3(9) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
B01 N01 1.574(11) 4
B01 N01 1.574(11) .
B01 C301 1.654(11) 4
B01 C301 1.654(11) .
N01 C101 1.363(10) .
N01 C201 1.430(9) .
F302 C302 1.383(10) .
F303 C303 1.346(10) .
F304 C304 1.346(10) .
F305 C305 1.339(10) .
F306 C306 1.350(9) .
C01 C204 1.523(12) .
C101 C101 1.428(16) 4
C101 C102 1.440(11) .
C102 C103 1.415(12) .
C102 C107 1.431(11) .
C103 C104 1.379(11) .
C104 C105 1.383(13) .
C105 C106 1.355(13) .
C106 C107 1.408(12) .
C107 C107 1.452(16) 4
C201 C206 1.384(10) .
C201 C202 1.390(11) .
C202 C203 1.381(11) .
C203 C204 1.390(12) .
C204 C205 1.388(12) .
C205 C206 1.393(11) .
C301 C306 1.379(11) .
C301 C302 1.389(12) .
C302 C303 1.386(13) .
C303 C304 1.370(13) .
C304 C305 1.345(13) .
C305 C306 1.347(12) .
