#------------------------------------------------------------------------------
#$Date: 2016-03-21 04:40:09 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178476 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/97/4029785.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_4029785
loop_
_publ_author_name
'Monot, Julien'
'Fensterbank, Louis'
'Malacria, Max'
'Lacôte, Emmanuel'
'Geib, Steven J.'
'Curran, Dennis P.'
_publ_section_title
;
 CAAC Boranes. Synthesis and characterization of cyclic (alkyl) (amino)
 carbene borane complexes from BF₃ and BH₃.
;
_journal_name_full               'Beilstein journal of organic chemistry'
_journal_page_first              709
_journal_page_last               712
_journal_paper_doi               10.3762/bjoc.6.82
_journal_volume                  6
_journal_year                    2010
_chemical_formula_sum            'C23 H35 B F3 N'
_chemical_formula_weight         393.33
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           11
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yb'
_symmetry_space_group_name_H-M   'P 1 21/m 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                 106.162(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   8.0309(17)
_cell_length_b                   14.995(3)
_cell_length_c                   9.5461(19)
_cell_measurement_reflns_used    1926
_cell_measurement_temperature    203(2)
_cell_measurement_theta_max      30.35
_cell_measurement_theta_min      2.221
_cell_volume                     1104.1(4)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      203(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0593
_diffrn_reflns_av_sigmaI/netI    0.0540
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            10726
_diffrn_reflns_theta_full        27.50
_diffrn_reflns_theta_max         27.50
_diffrn_reflns_theta_min         2.22
_exptl_absorpt_coefficient_mu    0.085
_exptl_absorpt_correction_T_max  0.9883
_exptl_absorpt_correction_T_min  0.9792
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker Sadabs'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.183
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             424
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.14
_refine_diff_density_max         0.452
_refine_diff_density_min         -0.296
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.363
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         2639
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.363
_refine_ls_R_factor_all          0.0889
_refine_ls_R_factor_gt           0.0647
_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)+(0.0780P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1772
_refine_ls_wR_factor_ref         0.1880
_reflns_number_gt                1893
_reflns_number_total             2639
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            1860-5397-6-82-S3.cif
_cod_data_source_block           jm4554s
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/automatic-downloads/retrospective/Beilstein/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_cell_volume        1104.2(4)
_cod_original_sg_symbol_H-M      'P 21/m'
_cod_database_code               4029785
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, 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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
N N 0.7274(2) 0.2500 0.3129(2) 0.0263(5) Uani 1 2 d S
B B 0.9960(3) 0.2500 0.5483(3) 0.0303(6) Uani 1 2 d S
F1 F 1.10136(18) 0.2500 0.45697(17) 0.0460(5) Uani 1 2 d S
C1 C 0.7854(3) 0.2500 0.4536(3) 0.0276(5) Uani 1 2 d S
F2 F 1.02691(14) 0.17511(9) 0.63500(16) 0.0616(5) Uani 1 1 d .
C2 C 0.6377(3) 0.2500 0.5235(3) 0.0337(6) Uani 1 2 d S
C3 C 0.4756(4) 0.2500 0.3945(3) 0.0660(11) Uani 1 2 d S
H3A H 0.4056 0.1970 0.3985 0.079 Uiso 0.50 1 calc PR
H3B H 0.4056 0.3030 0.3985 0.079 Uiso 0.50 1 calc PR
C4 C 0.5277(3) 0.2500 0.2540(3) 0.0304(5) Uani 1 2 d S
C5 C 0.6457(3) 0.1679(2) 0.6172(4) 0.0841(11) Uani 1 1 d .
H5A H 0.7582 0.1655 0.6910 0.101 Uiso 1 1 calc R
H5B H 0.6347 0.1144 0.5563 0.101 Uiso 1 1 calc R
C6 C 0.4992(4) 0.1691(4) 0.6929(5) 0.130(2) Uani 1 1 d .
H6A H 0.3875 0.1641 0.6185 0.156 Uiso 1 1 calc R
H6B H 0.5116 0.1169 0.7568 0.156 Uiso 1 1 calc R
C7 C 0.4983(6) 0.2500 0.7797(6) 0.185(5) Uani 1 2 d S
H7A H 0.3949 0.2500 0.8151 0.222 Uiso 1 2 calc SR
H7B H 0.6005 0.2500 0.8647 0.222 Uiso 1 2 calc SR
C8 C 0.4667(3) 0.16783(15) 0.1620(3) 0.0539(6) Uani 1 1 d .
H8A H 0.5039 0.1149 0.2208 0.081 Uiso 1 1 calc R
H8B H 0.5160 0.1675 0.0801 0.081 Uiso 1 1 calc R
H8C H 0.3412 0.1684 0.1263 0.081 Uiso 1 1 calc R
C9 C 0.8302(3) 0.2500 0.2090(3) 0.0274(5) Uani 1 2 d S
C10 C 0.8755(2) 0.16824(12) 0.1587(2) 0.0324(4) Uani 1 1 d .
C11 C 0.9540(2) 0.17083(14) 0.0458(2) 0.0405(5) Uani 1 1 d .
H11 H 0.9835 0.1170 0.0084 0.049 Uiso 1 1 calc R
C12 C 0.9894(3) 0.2500 -0.0123(3) 0.0425(7) Uani 1 2 d S
H12 H 1.0377 0.2500 -0.0914 0.051 Uiso 1 2 calc SR
C13 C 0.8608(3) 0.07869(12) 0.2292(2) 0.0418(5) Uani 1 1 d .
H13 H 0.7939 0.0875 0.3010 0.050 Uiso 1 1 calc R
C14 C 1.0430(3) 0.04514(14) 0.3116(3) 0.0539(6) Uani 1 1 d .
H14A H 1.1100 0.0348 0.2428 0.081 Uiso 1 1 calc R
H14B H 1.0331 -0.0101 0.3615 0.081 Uiso 1 1 calc R
H14C H 1.1008 0.0896 0.3823 0.081 Uiso 1 1 calc R
C15 C 0.7672(3) 0.00773(15) 0.1187(3) 0.0621(7) Uani 1 1 d .
H15A H 0.6512 0.0283 0.0693 0.093 Uiso 1 1 calc R
H15B H 0.7603 -0.0475 0.1695 0.093 Uiso 1 1 calc R
H15C H 0.8313 -0.0023 0.0477 0.093 Uiso 1 1 calc R
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
C1 N C9 126.76(18) . .
C1 N C4 114.56(18) . .
C9 N C4 118.68(18) . .
F1 B F2 109.99(14) . 4_565
F1 B F2 109.99(14) . .
F2 B F2 109.4(2) 4_565 .
F1 B C1 111.4(2) . .
F2 B C1 108.04(14) 4_565 .
F2 B C1 108.03(14) . .
N C1 C2 110.94(19) . .
N C1 B 125.2(2) . .
C2 C1 B 123.9(2) . .
C5 C2 C5 109.0(3) . 4_565
C5 C2 C1 110.55(14) . .
C5 C2 C1 110.55(14) 4_565 .
C5 C2 C3 111.34(17) . .
C5 C2 C3 111.34(17) 4_565 .
C1 C2 C3 104.0(2) . .
C4 C3 C2 109.4(2) . .
C4 C3 H3A 109.8 . .
C2 C3 H3A 109.8 . .
C4 C3 H3B 109.8 . .
C2 C3 H3B 109.8 . .
H3A C3 H3B 108.3 . .
C3 C4 C8 112.95(14) . .
C3 C4 C8 112.95(14) . 4_565
C8 C4 C8 109.0(2) . 4_565
C3 C4 N 101.14(19) . .
C8 C4 N 110.29(13) . .
C8 C4 N 110.29(13) 4_565 .
C2 C5 C6 110.8(2) . .
C2 C5 H5A 109.5 . .
C6 C5 H5A 109.5 . .
C2 C5 H5B 109.5 . .
C6 C5 H5B 109.5 . .
H5A C5 H5B 108.1 . .
C7 C6 C5 113.5(4) . .
C7 C6 H6A 108.9 . .
C5 C6 H6A 108.9 . .
C7 C6 H6B 108.9 . .
C5 C6 H6B 108.9 . .
H6A C6 H6B 107.7 . .
C6 C7 C6 111.2(4) 4_565 .
C6 C7 H7A 109.4 4_565 .
C6 C7 H7A 109.4 . .
C6 C7 H7B 109.4 4_565 .
C6 C7 H7B 109.4 . .
H7A C7 H7B 108.0 . .
C4 C8 H8A 109.5 . .
C4 C8 H8B 109.5 . .
H8A C8 H8B 109.5 . .
C4 C8 H8C 109.5 . .
H8A C8 H8C 109.5 . .
H8B C8 H8C 109.5 . .
C10 C9 C10 122.1(2) . 4_565
C10 C9 N 118.94(11) . .
C10 C9 N 118.94(11) 4_565 .
C11 C10 C9 117.23(17) . .
C11 C10 C13 118.31(16) . .
C9 C10 C13 124.17(16) . .
C12 C11 C10 121.75(18) . .
C12 C11 H11 119.1 . .
C10 C11 H11 119.1 . .
C11 C12 C11 119.6(2) . 4_565
C11 C12 H12 120.2 . .
C11 C12 H12 120.2 4_565 .
C10 C13 C14 109.55(16) . .
C10 C13 C15 113.00(18) . .
C14 C13 C15 109.72(17) . .
C10 C13 H13 108.1 . .
C14 C13 H13 108.1 . .
C15 C13 H13 108.1 . .
C13 C14 H14A 109.5 . .
C13 C14 H14B 109.5 . .
H14A C14 H14B 109.5 . .
C13 C14 H14C 109.5 . .
H14A C14 H14C 109.5 . .
H14B C14 H14C 109.5 . .
C13 C15 H15A 109.5 . .
C13 C15 H15B 109.5 . .
H15A C15 H15B 109.5 . .
C13 C15 H15C 109.5 . .
H15A C15 H15C 109.5 . .
H15B C15 H15C 109.5 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
N C1 1.293(3) .
N C9 1.456(3) .
N C4 1.544(3) .
B F1 1.373(3) .
B F2 1.376(2) 4_565
B F2 1.376(2) .
B C1 1.681(3) .
C1 C2 1.514(3) .
C2 C5 1.513(3) .
C2 C5 1.513(3) 4_565
C2 C3 1.523(4) .
C3 C4 1.512(4) .
C3 H3A 0.9800 .
C3 H3B 0.9800 .
C4 C8 1.513(2) .
C4 C8 1.513(2) 4_565
C5 C6 1.543(4) .
C5 H5A 0.9800 .
C5 H5B 0.9800 .
C6 C7 1.470(6) .
C6 H6A 0.9800 .
C6 H6B 0.9800 .
C7 C6 1.470(6) 4_565
C7 H7A 0.9800 .
C7 H7B 0.9800 .
C8 H8A 0.9700 .
C8 H8B 0.9700 .
C8 H8C 0.9700 .
C9 C10 1.401(2) .
C9 C10 1.401(2) 4_565
C10 C11 1.393(3) .
C10 C13 1.521(3) .
C11 C12 1.373(2) .
C11 H11 0.9400 .
C12 C11 1.373(2) 4_565
C12 H12 0.9400 .
C13 C14 1.540(3) .
C13 C15 1.539(3) .
C13 H13 0.9900 .
C14 H14A 0.9700 .
C14 H14B 0.9700 .
C14 H14C 0.9700 .
C15 H15A 0.9700 .
C15 H15B 0.9700 .
C15 H15C 0.9700 .
