#------------------------------------------------------------------------------
#$Date: 2016-03-21 03:02:44 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178417 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/38/4023856.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_4023856
loop_
_publ_author_name
'Vincent Terrasson'
'José G. Planas'
'Damien Prim'
'Clara Viñas'
'Francesc Teixidor'
'Mark E. Light'
'Michael B. Hursthouse'
_publ_section_title
;
 Cooperative Effect of Carborane and Pyridine in the Reaction of
 Carboranyl Alcohols with Thionyl Chloride:
 Halogenation versus Oxidation
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              9140
_journal_page_last               9143
_journal_paper_doi               10.1021/jo801672f
_journal_volume                  73
_journal_year                    2008
_chemical_compound_source        'Jose Giner Planas'
_chemical_formula_sum            'C9 H17 B10 N O'
_chemical_formula_weight         263.34
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_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                 100.493(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.6062(2)
_cell_length_b                   9.7769(3)
_cell_length_c                   15.5918(4)
_cell_measurement_reflns_used    10483
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.91
_cell_volume                     1439.88(6)
_computing_cell_refinement
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_data_collection       'COLLECT (Hooft, R.W.W., 1998)'
_computing_data_reduction
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, R.W.W., 1998)'
_computing_molecular_graphics    'CAMERON (Watkin, et al., 1993)'
_computing_publication_material  'WINGX (Farrugia, 1998)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      120(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker-Nonius CCD camera on κ-goniostat'
_diffrn_measurement_method       'φ & ω scans to fill the asymmetric unit'
_diffrn_radiation_monochromator  '10cm confocal mirrors'
_diffrn_radiation_source         'Bruker Nonius FR591 Rotating Anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0844
_diffrn_reflns_av_sigmaI/netI    0.0507
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            15352
_diffrn_reflns_theta_full        25.03
_diffrn_reflns_theta_max         25.03
_diffrn_reflns_theta_min         3.00
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.065
_exptl_absorpt_correction_T_max  0.9974
_exptl_absorpt_correction_T_min  0.9810
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS V2.10 (Sheldrick, G.M., 2003)
;
_exptl_crystal_colour            'Pale Yellow'
_exptl_crystal_density_diffrn    1.215
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Fragment
_exptl_crystal_F_000             544
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.333
_refine_diff_density_min         -0.352
_refine_diff_density_rms         0.057
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2542
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.0891
_refine_ls_R_factor_gt           0.0666
_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)+(0.0489P)²+2.5288P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1475
_refine_ls_wR_factor_ref         0.1636
_reflns_number_gt                2009
_reflns_number_total             2542
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo801672f_si_005.cif
_cod_data_source_block           2007acc1649
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4023856
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
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.5941(3) 0.6459(3) 0.17062(15) 0.0196(6) Uani 1 1 d . . .
C2 C 0.6855(3) 0.6710(3) 0.27171(15) 0.0210(6) Uani 1 1 d . . .
C3 C 0.6113(3) 0.7202(3) 0.34372(17) 0.0294(7) Uani 1 1 d . . .
H3A H 0.6804 0.7293 0.3980 0.044 Uiso 1 1 calc R . .
H3B H 0.5384 0.6539 0.3521 0.044 Uiso 1 1 calc R . .
H3C H 0.5671 0.8091 0.3277 0.044 Uiso 1 1 calc R . .
C4 C 0.4319(3) 0.6612(3) 0.15902(17) 0.0242(6) Uani 1 1 d . . .
C5 C 0.3490(3) 0.7424(3) 0.08562(16) 0.0209(6) Uani 1 1 d . . .
C6 C 0.2061(3) 0.7105(3) 0.06064(17) 0.0250(6) Uani 1 1 d . . .
H6 H 0.1641 0.6404 0.0895 0.030 Uiso 1 1 calc R . .
C7 C 0.1269(3) 0.7832(3) -0.00713(17) 0.0294(7) Uani 1 1 d . . .
H7 H 0.0296 0.7626 -0.0267 0.035 Uiso 1 1 calc R . .
C8 C 0.1917(3) 0.8861(3) -0.04597(17) 0.0276(6) Uani 1 1 d . . .
H8 H 0.1398 0.9373 -0.0930 0.033 Uiso 1 1 calc R . .
C9 C 0.3332(3) 0.9139(3) -0.01555(17) 0.0270(6) Uani 1 1 d . . .
H9 H 0.3760 0.9865 -0.0418 0.032 Uiso 1 1 calc R . .
B3 B 0.7024(3) 0.7869(3) 0.18890(18) 0.0205(6) Uani 1 1 d . . .
H3 H 0.6638 0.8952 0.1857 0.025 Uiso 1 1 calc R . .
B4 B 0.6949(3) 0.6831(3) 0.09402(19) 0.0222(7) Uani 1 1 d . . .
H4 H 0.6521 0.7240 0.0273 0.027 Uiso 1 1 calc R . .
B5 B 0.6638(3) 0.5108(3) 0.12228(19) 0.0233(7) Uani 1 1 d . . .
H5 H 0.5997 0.4393 0.0746 0.028 Uiso 1 1 calc R . .
B6 B 0.6564(3) 0.5053(3) 0.23567(19) 0.0213(6) Uani 1 1 d . . .
H6A H 0.5872 0.4311 0.2631 0.026 Uiso 1 1 calc R . .
B7 B 0.8508(3) 0.7295(3) 0.26692(19) 0.0235(7) Uani 1 1 d . . .
H7A H 0.9110 0.8023 0.3155 0.028 Uiso 1 1 calc R . .
B8 B 0.8614(3) 0.7355(3) 0.15442(19) 0.0220(6) Uani 1 1 d . . .
H8A H 0.9299 0.8115 0.1280 0.026 Uiso 1 1 calc R . .
B9 B 0.8372(3) 0.5651(3) 0.1129(2) 0.0234(7) Uani 1 1 d . . .
H9A H 0.8899 0.5284 0.0587 0.028 Uiso 1 1 calc R . .
B10 B 0.8124(3) 0.4542(3) 0.20015(19) 0.0241(7) Uani 1 1 d . . .
H10 H 0.8479 0.3449 0.2035 0.029 Uiso 1 1 calc R . .
B11 B 0.8225(3) 0.5567(3) 0.29492(19) 0.0232(7) Uani 1 1 d . . .
H11 H 0.8645 0.5155 0.3616 0.028 Uiso 1 1 calc R . .
B12 B 0.9355(3) 0.5941(3) 0.21987(19) 0.0240(7) Uani 1 1 d . . .
H12 H 1.0526 0.5772 0.2363 0.029 Uiso 1 1 calc R . .
N1 N 0.4136(2) 0.8433(2) 0.04932(14) 0.0244(5) Uani 1 1 d . . .
O1 O 0.3712(2) 0.6019(2) 0.20915(14) 0.0422(6) 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'
O O 0.0106 0.0060 '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
_geom_angle_publ_flag
C4 C1 C2 116.2(2) . . ?
C4 C1 B4 125.9(2) . . ?
C2 C1 B4 111.07(19) . . ?
C4 C1 B5 119.3(2) . . ?
C2 C1 B5 110.23(19) . . ?
B4 C1 B5 62.64(17) . . ?
C4 C1 B3 120.7(2) . . ?
C2 C1 B3 61.92(15) . . ?
B4 C1 B3 62.76(16) . . ?
B5 C1 B3 114.7(2) . . ?
C4 C1 B6 112.1(2) . . ?
C2 C1 B6 60.27(15) . . ?
B4 C1 B6 113.3(2) . . ?
B5 C1 B6 61.93(16) . . ?
B3 C1 B6 113.65(19) . . ?
C3 C2 C1 120.4(2) . . ?
C3 C2 B7 119.7(2) . . ?
C1 C2 B7 109.94(19) . . ?
C3 C2 B11 119.8(2) . . ?
C1 C2 B11 110.72(19) . . ?
B7 C2 B11 62.76(17) . . ?
C3 C2 B6 118.1(2) . . ?
C1 C2 B6 61.92(15) . . ?
B7 C2 B6 113.6(2) . . ?
B11 C2 B6 61.83(16) . . ?
C3 C2 B3 117.5(2) . . ?
C1 C2 B3 60.23(15) . . ?
B7 C2 B3 62.40(16) . . ?
B11 C2 B3 114.1(2) . . ?
B6 C2 B3 113.61(19) . . ?
O1 C4 C5 119.9(2) . . ?
O1 C4 C1 118.3(2) . . ?
C5 C4 C1 121.7(2) . . ?
N1 C5 C6 123.7(2) . . ?
N1 C5 C4 119.3(2) . . ?
C6 C5 C4 117.0(2) . . ?
C7 C6 C5 118.4(3) . . ?
C8 C7 C6 118.8(2) . . ?
C7 C8 C9 119.1(3) . . ?
N1 C9 C8 123.4(3) . . ?
C1 B3 C2 57.86(14) . . ?
C1 B3 B8 104.5(2) . . ?
C2 B3 B8 103.9(2) . . ?
C1 B3 B4 58.32(16) . . ?
C2 B3 B4 104.4(2) . . ?
B8 B3 B4 59.80(16) . . ?
C1 B3 B7 104.2(2) . . ?
C2 B3 B7 57.55(15) . . ?
B8 B3 B7 59.73(16) . . ?
B4 B3 B7 107.0(2) . . ?
C1 B4 B9 105.3(2) . . ?
C1 B4 B8 105.12(19) . . ?
B9 B4 B8 60.48(16) . . ?
C1 B4 B5 58.91(16) . . ?
B9 B4 B5 60.16(17) . . ?
B8 B4 B5 108.5(2) . . ?
C1 B4 B3 58.92(15) . . ?
B9 B4 B3 108.6(2) . . ?
B8 B4 B3 60.00(16) . . ?
B5 B4 B3 108.4(2) . . ?
C1 B5 B4 58.45(16) . . ?
C1 B5 B9 104.6(2) . . ?
B4 B5 B9 59.68(17) . . ?
C1 B5 B6 59.92(16) . . ?
B4 B5 B6 108.2(2) . . ?
B9 B5 B6 107.3(2) . . ?
C1 B5 B10 105.5(2) . . ?
B4 B5 B10 108.2(2) . . ?
B9 B5 B10 60.25(16) . . ?
B6 B5 B10 59.17(16) . . ?
C2 B6 C1 57.80(15) . . ?
C2 B6 B10 105.8(2) . . ?
C1 B6 B10 105.2(2) . . ?
C2 B6 B11 58.87(16) . . ?
C1 B6 B11 105.1(2) . . ?
B10 B6 B11 60.40(17) . . ?
C2 B6 B5 105.2(2) . . ?
C1 B6 B5 58.15(16) . . ?
B10 B6 B5 60.49(16) . . ?
B11 B6 B5 108.4(2) . . ?
C2 B7 B8 106.0(2) . . ?
C2 B7 B11 58.94(16) . . ?
B8 B7 B11 108.2(2) . . ?
C2 B7 B12 105.5(2) . . ?
B8 B7 B12 60.33(17) . . ?
B11 B7 B12 59.77(17) . . ?
C2 B7 B3 60.06(15) . . ?
B8 B7 B3 59.97(16) . . ?
B11 B7 B3 109.1(2) . . ?
B12 B7 B3 108.7(2) . . ?
B4 B8 B7 107.8(2) . . ?
B4 B8 B3 60.21(16) . . ?
B7 B8 B3 60.31(16) . . ?
B4 B8 B12 107.8(2) . . ?
B7 B8 B12 59.95(17) . . ?
B3 B8 B12 108.7(2) . . ?
B4 B8 B9 59.60(17) . . ?
B7 B8 B9 107.5(2) . . ?
B3 B8 B9 108.1(2) . . ?
B12 B8 B9 59.85(17) . . ?
B4 B9 B5 60.16(16) . . ?
B4 B9 B12 108.2(2) . . ?
B5 B9 B12 108.3(2) . . ?
B4 B9 B8 59.92(16) . . ?
B5 B9 B8 108.1(2) . . ?
B12 B9 B8 60.09(17) . . ?
B4 B9 B10 108.4(2) . . ?
B5 B9 B10 60.03(17) . . ?
B12 B9 B10 60.41(17) . . ?
B8 B9 B10 108.4(2) . . ?
B6 B10 B11 59.87(16) . . ?
B6 B10 B5 60.34(16) . . ?
B11 B10 B5 107.9(2) . . ?
B6 B10 B9 107.8(2) . . ?
B11 B10 B9 107.2(2) . . ?
B5 B10 B9 59.72(16) . . ?
B6 B10 B12 107.5(2) . . ?
B11 B10 B12 59.54(17) . . ?
B5 B10 B12 107.5(2) . . ?
B9 B10 B12 59.62(17) . . ?
C2 B11 B6 59.29(16) . . ?
C2 B11 B12 105.4(2) . . ?
B6 B11 B12 108.5(2) . . ?
C2 B11 B10 105.6(2) . . ?
B6 B11 B10 59.73(16) . . ?
B12 B11 B10 60.90(17) . . ?
C2 B11 B7 58.30(16) . . ?
B6 B11 B7 107.8(2) . . ?
B12 B11 B7 60.19(17) . . ?
B10 B11 B7 108.7(2) . . ?
B11 B12 B7 60.04(17) . . ?
B11 B12 B9 107.5(2) . . ?
B7 B12 B9 107.4(2) . . ?
B11 B12 B8 107.9(2) . . ?
B7 B12 B8 59.71(17) . . ?
B9 B12 B8 60.06(16) . . ?
B11 B12 B10 59.56(17) . . ?
B7 B12 B10 107.5(2) . . ?
B9 B12 B10 59.96(17) . . ?
B8 B12 B10 108.1(2) . . ?
C5 N1 C9 116.6(2) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C4 1.543(3) . ?
C1 C2 1.677(3) . ?
C1 B4 1.708(4) . ?
C1 B5 1.716(4) . ?
C1 B3 1.719(4) . ?
C1 B6 1.748(4) . ?
C2 C3 1.514(4) . ?
C2 B7 1.702(4) . ?
C2 B11 1.713(4) . ?
C2 B6 1.721(4) . ?
C2 B3 1.747(4) . ?
C4 O1 1.205(3) . ?
C4 C5 1.498(4) . ?
C5 N1 1.344(3) . ?
C5 C6 1.392(4) . ?
C6 C7 1.381(4) . ?
C7 C8 1.380(4) . ?
C8 C9 1.383(4) . ?
C9 N1 1.345(3) . ?
B3 B8 1.781(4) . ?
B3 B4 1.785(4) . ?
B3 B7 1.787(4) . ?
B4 B9 1.772(4) . ?
B4 B8 1.777(4) . ?
B4 B5 1.780(4) . ?
B5 B9 1.780(4) . ?
B5 B6 1.783(4) . ?
B5 B10 1.786(4) . ?
B6 B10 1.762(4) . ?
B6 B11 1.765(4) . ?
B7 B8 1.777(4) . ?
B7 B11 1.778(4) . ?
B7 B12 1.781(4) . ?
B8 B12 1.788(4) . ?
B8 B9 1.787(4) . ?
B9 B12 1.783(4) . ?
B9 B10 1.790(4) . ?
B10 B11 1.774(4) . ?
B10 B12 1.798(4) . ?
B11 B12 1.773(4) . ?
