#------------------------------------------------------------------------------
#$Date: 2016-02-14 15:26:36 +0100 (dom 14 de feb de 2016) $
#$Revision: 176435 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/30/1503028.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_1503028
loop_
_publ_author_name
'Solovyev, Andrey'
'Ueng, Shau-Hua'
'Monot, Julien'
'Fensterbank, Louis'
'Malacria, Max'
'Lacôte, Emmanuel'
'Curran, Dennis P.'
_publ_section_title
;
 Estimated rate constants for hydrogen abstraction from N-heterocyclic
 carbene-borane complexes by an alkyl radical.
;
_journal_issue                   13
_journal_name_full               'Organic letters'
_journal_page_first              2998
_journal_page_last               3001
_journal_paper_doi               10.1021/ol101014q
_journal_volume                  12
_journal_year                    2010
_chemical_formula_moiety         'C9 H19 B1 N2'
_chemical_formula_sum            'C9 H19 B N2'
_chemical_formula_weight         166.07
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 117.492(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   10.567(5)
_cell_length_b                   10.864(4)
_cell_length_c                   10.851(9)
_cell_measurement_reflns_used    18
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      18
_cell_measurement_theta_min      3
_cell_volume                     1105.0(11)
_computing_cell_refinement
'Dirax/lsq (Duisenberg & Schreurs, 1989-2000)'
_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_data_reduction        'EvalCCD (Duisenberg & Schreurs 1990-2000)'
_computing_molecular_graphics    'DIAMOND (Brandenburg, 1999)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR-92 (Giacovazzo, 1993)'
_diffrn_ambient_temperature      200(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_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  0.0434
_diffrn_reflns_av_sigmaI/netI    0.0583
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            11029
_diffrn_reflns_theta_full        30.01
_diffrn_reflns_theta_max         30.01
_diffrn_reflns_theta_min         3.76
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.058
_exptl_absorpt_correction_T_max  0.994
_exptl_absorpt_correction_T_min  0.692
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
R.H. Blessing, Acta Cryst. (1995), A51, 33-38
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    0.998
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       stick
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.230
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       0.029(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     114
_refine_ls_number_reflns         3164
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.019
_refine_ls_R_factor_all          0.1004
_refine_ls_R_factor_gt           0.0512
_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)+(0.0623P)²+0.1252P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1195
_refine_ls_wR_factor_ref         0.1376
_reflns_number_gt                1901
_reflns_number_total             3164
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol101014q_si_002.cif
_cod_data_source_block           jm401
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_original_formula_sum        'C9 H19 B1 N2'
_cod_database_code               1503028
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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
N1 N 0.22635(10) 0.21550(10) 0.67461(10) 0.0310(3) Uani 1 1 d .
N2 N 0.41791(10) 0.23330(9) 0.65447(10) 0.0298(3) Uani 1 1 d .
C1 C 0.30382(12) 0.15932(11) 0.62106(12) 0.0270(3) Uani 1 1 d .
C2 C 0.29128(14) 0.32289(12) 0.74132(14) 0.0373(3) Uani 1 1 d .
H2 H 0.2583 0.3774 0.7862 0.045 Uiso 1 1 calc R
C3 C 0.41107(14) 0.33340(13) 0.72897(14) 0.0369(3) Uani 1 1 d .
H3 H 0.4775 0.3967 0.7643 0.044 Uiso 1 1 calc R
C4 C 0.09156(12) 0.16795(13) 0.66488(14) 0.0359(3) Uani 1 1 d .
H4 H 0.0599 0.0995 0.5986 0.043 Uiso 1 1 calc R
C5 C -0.02155(15) 0.26612(17) 0.61047(19) 0.0621(5) Uani 1 1 d .
H5A H 0.0024 0.3303 0.6784 0.093 Uiso 1 1 calc R
H5B H -0.1119 0.2310 0.5920 0.093 Uiso 1 1 calc R
H5C H -0.0273 0.2998 0.5262 0.093 Uiso 1 1 calc R
C6 C 0.11442(17) 0.11924(18) 0.80359(17) 0.0584(5) Uani 1 1 d .
H6A H 0.1851 0.0553 0.8335 0.088 Uiso 1 1 calc R
H6B H 0.0263 0.0866 0.7952 0.088 Uiso 1 1 calc R
H6C H 0.1464 0.1848 0.8705 0.088 Uiso 1 1 calc R
C7 C 0.53505(12) 0.21197(12) 0.61899(13) 0.0328(3) Uani 1 1 d .
H7 H 0.5077 0.1439 0.5523 0.039 Uiso 1 1 calc R
C8 C 0.55883(16) 0.32549(15) 0.55112(16) 0.0471(4) Uani 1 1 d .
H8A H 0.4705 0.3493 0.4735 0.071 Uiso 1 1 calc R
H8B H 0.6280 0.3076 0.5195 0.071 Uiso 1 1 calc R
H8C H 0.5930 0.3915 0.6174 0.071 Uiso 1 1 calc R
C9 C 0.66888(13) 0.17508(14) 0.74792(15) 0.0415(4) Uani 1 1 d .
H9A H 0.7014 0.2430 0.8117 0.062 Uiso 1 1 calc R
H9B H 0.7417 0.1527 0.7226 0.062 Uiso 1 1 calc R
H9C H 0.6484 0.1062 0.7912 0.062 Uiso 1 1 calc R
B1 B 0.26430(15) 0.03140(13) 0.53826(15) 0.0320(3) Uani 1 1 d .
H11 H 0.1706 0.0470 0.4436 0.038 Uiso 1 1 d R
H12 H 0.3563 0.0017 0.5147 0.038 Uiso 1 1 d R
H13 H 0.2399 -0.0365 0.6024 0.038 Uiso 1 1 d R
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
N1 0.0245(5) 0.0327(6) 0.0352(6) -0.0069(5) 0.0133(4) -0.0023(4)
N2 0.0257(5) 0.0308(6) 0.0328(5) -0.0043(5) 0.0135(4) -0.0024(4)
C1 0.0229(5) 0.0289(6) 0.0259(6) 0.0009(5) 0.0084(4) 0.0015(5)
C2 0.0341(7) 0.0353(7) 0.0428(8) -0.0130(6) 0.0180(6) -0.0029(6)
C3 0.0331(7) 0.0326(7) 0.0434(7) -0.0128(6) 0.0163(6) -0.0068(6)
C4 0.0243(6) 0.0412(8) 0.0426(7) -0.0083(6) 0.0159(5) -0.0055(6)
C5 0.0283(7) 0.0727(12) 0.0784(12) 0.0127(10) 0.0189(7) 0.0062(8)
C6 0.0463(9) 0.0709(12) 0.0598(10) 0.0077(9) 0.0261(8) -0.0126(8)
C7 0.0271(6) 0.0373(7) 0.0370(7) -0.0063(6) 0.0173(5) -0.0030(5)
C8 0.0452(8) 0.0538(9) 0.0479(9) 0.0051(7) 0.0262(7) -0.0042(7)
C9 0.0296(7) 0.0471(9) 0.0475(8) -0.0016(7) 0.0177(6) 0.0037(6)
B1 0.0342(7) 0.0266(7) 0.0340(7) -0.0026(6) 0.0146(6) -0.0019(6)
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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C1 N1 C2 110.82(11)
C1 N1 C4 124.73(11)
C2 N1 C4 124.44(11)
C1 N2 C3 110.18(11)
C1 N2 C7 126.07(11)
C3 N2 C7 123.74(11)
N1 C1 N2 105.00(11)
N1 C1 B1 125.54(11)
N2 C1 B1 129.46(11)
C3 C2 N1 106.53(12)
C3 C2 H2 126.7
N1 C2 H2 126.7
C2 C3 N2 107.45(12)
C2 C3 H3 126.3
N2 C3 H3 126.3
N1 C4 C5 110.27(12)
N1 C4 C6 110.36(12)
C5 C4 C6 111.91(14)
N1 C4 H4 108.1
C5 C4 H4 108.1
C6 C4 H4 108.1
C4 C5 H5A 109.5
C4 C5 H5B 109.5
H5A C5 H5B 109.5
C4 C5 H5C 109.5
H5A C5 H5C 109.5
H5B C5 H5C 109.5
C4 C6 H6A 109.5
C4 C6 H6B 109.5
H6A C6 H6B 109.5
C4 C6 H6C 109.5
H6A C6 H6C 109.5
H6B C6 H6C 109.5
N2 C7 C9 109.82(11)
N2 C7 C8 110.27(11)
C9 C7 C8 111.76(11)
N2 C7 H7 108.3
C9 C7 H7 108.3
C8 C7 H7 108.3
C7 C8 H8A 109.5
C7 C8 H8B 109.5
H8A C8 H8B 109.5
C7 C8 H8C 109.5
H8A C8 H8C 109.5
H8B C8 H8C 109.5
C7 C9 H9A 109.5
C7 C9 H9B 109.5
H9A C9 H9B 109.5
C7 C9 H9C 109.5
H9A C9 H9C 109.5
H9B C9 H9C 109.5
C1 B1 H11 106.8
C1 B1 H12 109.7
H11 B1 H12 109.5
C1 B1 H13 107.3
H11 B1 H13 109.1
H12 B1 H13 114.1
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C1 1.3489(16)
N1 C2 1.3775(17)
N1 C4 1.4723(16)
N2 C1 1.3518(16)
N2 C3 1.3768(17)
N2 C7 1.4743(16)
C1 B1 1.6020(19)
C2 C3 1.3378(19)
C2 H2 0.9300
C3 H3 0.9300
C4 C5 1.504(2)
C4 C6 1.506(2)
C4 H4 0.9800
C5 H5A 0.9600
C5 H5B 0.9600
C5 H5C 0.9600
C6 H6A 0.9600
C6 H6B 0.9600
C6 H6C 0.9600
C7 C9 1.514(2)
C7 C8 1.516(2)
C7 H7 0.9800
C8 H8A 0.9600
C8 H8B 0.9600
C8 H8C 0.9600
C9 H9A 0.9600
C9 H9B 0.9600
C9 H9C 0.9600
B1 H11 1.0603
B1 H12 1.1595
B1 H13 1.1231
