#------------------------------------------------------------------------------
#$Date: 2016-03-21 13:55:20 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178707 $
#$URL: svn://www.crystallography.net/cod/cif/4/08/18/4081862.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_4081862
loop_
_publ_author_name
'Harlow, Gregory P.'
'Zakharov, Lev N.'
'Wu, Gang'
'Liu, Shih-Yuan'
_publ_section_title
;
 Thermodynamically Controlled, Dynamic Binding of Diols to a 1,2-BN
 Cyclohexane Derivative
;
_journal_issue                   22
_journal_name_full               Organometallics
_journal_page_first              6650
_journal_paper_doi               10.1021/om400697r
_journal_volume                  32
_journal_year                    2013
_chemical_formula_sum            'C14 H22 B N O2'
_chemical_formula_weight         247.14
_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   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXLTL
_cell_angle_alpha                90.00
_cell_angle_beta                 112.0740(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.1581(4)
_cell_length_b                   17.0898(8)
_cell_length_c                   9.3556(4)
_cell_measurement_reflns_used    5771
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      27.82
_cell_measurement_theta_min      2.38
_cell_volume                     1356.92(10)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_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  0.0207
_diffrn_reflns_av_sigmaI/netI    0.0138
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            12850
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.38
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_T_max  0.9830
_exptl_absorpt_correction_T_min  0.9731
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   SADABS
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.210
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.702
_refine_diff_density_min         -0.358
_refine_diff_density_rms         0.041
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     252
_refine_ls_number_reflns         2387
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.086
_refine_ls_R_factor_all          0.0583
_refine_ls_R_factor_gt           0.0570
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0450P)²+1.2520P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1284
_refine_ls_wR_factor_ref         0.1292
_reflns_number_gt                2312
_reflns_number_total             2387
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            om400697r_si_001.cif
_cod_data_source_block           liu186
_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 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 1891 2012-01-12 08:04:46Z andrius 
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               4081862
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
O1 O 0.22809(18) 0.95994(9) 0.12073(16) 0.0378(4) Uani 1 1 d
O2 O 0.40531(18) 1.04629(8) 0.32247(15) 0.0328(4) Uani 1 1 d
N1 N 0.31966(19) 0.92008(9) 0.38920(19) 0.0244(4) Uani 1 1 d
B1 B 0.3695(3) 0.96614(13) 0.2604(2) 0.0279(5) Uani 1 1 d
C1 C 0.3006(3) 0.83428(11) 0.3553(3) 0.0320(5) Uani 1 1 d
C2 C 0.4472(3) 0.79764(12) 0.3457(3) 0.0350(5) Uani 1 1 d
C3 C 0.4920(3) 0.83395(13) 0.2195(3) 0.0350(5) Uani 1 1 d
C4 C 0.5198(3) 0.92168(12) 0.2491(3) 0.0324(5) Uani 1 1 d
C5 C 0.1734(2) 0.95480(12) 0.4001(2) 0.0298(5) Uani 1 1 d
C6 C 0.1072(2) 0.90872(11) 0.4992(2) 0.0275(4) Uani 1 1 d
C7 C 0.1803(3) 0.90841(13) 0.6586(3) 0.0350(5) Uani 1 1 d
C8 C 0.1212(3) 0.86342(14) 0.7480(3) 0.0430(6) Uani 1 1 d
C9 C -0.0115(3) 0.81855(14) 0.6785(3) 0.0459(6) Uani 1 1 d
C10 C -0.0874(3) 0.81940(14) 0.5201(3) 0.0453(6) Uani 1 1 d
C11 C -0.0286(3) 0.86443(13) 0.4315(3) 0.0363(5) Uani 1 1 d
C12 C 0.2065(3) 1.01836(15) 0.0104(3) 0.0429(6) Uani 1 1 d
C13 C 0.2245(4) 1.09763(16) 0.0751(3) 0.0581(8) Uani 1 1 d
C14 C 0.3751(3) 1.10657(14) 0.2129(3) 0.0452(6) Uani 1 1 d
H1A H 0.272(3) 0.8084(13) 0.436(3) 0.034(6) Uiso 1 1 d
H1B H 0.211(3) 0.8296(13) 0.256(3) 0.031(6) Uiso 1 1 d
H1N H 0.400(3) 0.9272(12) 0.482(3) 0.025(5) Uiso 1 1 d
H2A H 0.431(3) 0.7417(16) 0.330(3) 0.046(7) Uiso 1 1 d
H2B H 0.537(3) 0.8029(13) 0.446(3) 0.035(6) Uiso 1 1 d
H3A H 0.582(3) 0.8071(14) 0.212(3) 0.038(6) Uiso 1 1 d
H3B H 0.405(3) 0.8258(14) 0.117(3) 0.040(6) Uiso 1 1 d
H4A H 0.614(3) 0.9281(13) 0.345(3) 0.034(6) Uiso 1 1 d
H4B H 0.543(3) 0.9471(14) 0.164(3) 0.039(6) Uiso 1 1 d
H5A H 0.201(3) 1.0076(14) 0.439(2) 0.032(6) Uiso 1 1 d
H5B H 0.097(3) 0.9570(12) 0.294(3) 0.029(5) Uiso 1 1 d
H7 H 0.275(3) 0.9402(15) 0.707(3) 0.045(7) Uiso 1 1 d
H8 H 0.173(3) 0.8641(15) 0.855(3) 0.049(7) Uiso 1 1 d
H9 H -0.052(3) 0.7869(17) 0.740(3) 0.062(8) Uiso 1 1 d
H10 H -0.182(3) 0.7880(16) 0.469(3) 0.056(8) Uiso 1 1 d
H11 H -0.080(3) 0.8652(14) 0.323(3) 0.046(7) Uiso 1 1 d
H12A H 0.105(3) 1.0102(15) -0.077(3) 0.049(7) Uiso 1 1 d
H12B H 0.292(3) 1.0100(17) -0.037(3) 0.060(8) Uiso 1 1 d
H13A H 0.123(4) 1.107(2) 0.118(4) 0.103(12) Uiso 1 1 d
H13B H 0.228(4) 1.1387(19) 0.000(4) 0.073(9) Uiso 1 1 d
H14A H 0.387(3) 1.1540(17) 0.267(3) 0.050(7) Uiso 1 1 d
H14B H 0.464(4) 1.104(2) 0.158(4) 0.083(10) Uiso 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
C12 O1 B1 116.23(17)
C14 O2 B1 116.08(17)
C1 N1 C5 111.41(15)
C1 N1 B1 110.91(15)
C5 N1 B1 111.19(15)
C1 N1 H1N 108.7(13)
C5 N1 H1N 108.0(13)
B1 N1 H1N 106.4(13)
O1 B1 O2 114.29(17)
O1 B1 C4 113.62(17)
O2 B1 C4 113.27(17)
O1 B1 N1 102.97(16)
O2 B1 N1 103.77(15)
C4 B1 N1 107.60(16)
N1 C1 C2 112.45(17)
N1 C1 H1A 108.6(13)
C2 C1 H1A 110.6(13)
N1 C1 H1B 105.6(13)
C2 C1 H1B 110.8(13)
H1A C1 H1B 108.7(18)
C1 C2 C3 112.39(18)
C1 C2 H2A 109.1(15)
C3 C2 H2A 110.7(15)
C1 C2 H2B 110.1(13)
C3 C2 H2B 109.2(13)
H2A C2 H2B 105.2(19)
C2 C3 C4 109.54(17)
C2 C3 H3A 110.4(14)
C4 C3 H3A 112.8(14)
C2 C3 H3B 109.9(14)
C4 C3 H3B 109.3(14)
H3A C3 H3B 104.8(19)
C3 C4 B1 112.73(17)
C3 C4 H4A 107.6(13)
B1 C4 H4A 111.4(13)
C3 C4 H4B 110.8(14)
B1 C4 H4B 106.9(14)
H4A C4 H4B 107.4(19)
N1 C5 C6 114.22(16)
N1 C5 H5A 106.4(13)
C6 C5 H5A 111.1(13)
N1 C5 H5B 105.3(13)
C6 C5 H5B 110.1(13)
H5A C5 H5B 109.4(18)
C7 C6 C11 118.4(2)
C7 C6 C5 121.37(19)
C11 C6 C5 120.21(19)
C6 C7 C8 120.7(2)
C6 C7 H7 118.8(15)
C8 C7 H7 120.5(15)
C9 C8 C7 120.0(2)
C9 C8 H8 121.0(16)
C7 C8 H8 119.1(16)
C8 C9 C10 120.0(2)
C8 C9 H9 120.1(17)
C10 C9 H9 119.9(17)
C11 C10 C9 119.8(2)
C11 C10 H10 118.9(16)
C9 C10 H10 121.2(16)
C10 C11 C6 121.0(2)
C10 C11 H11 120.2(15)
C6 C11 H11 118.8(15)
O1 C12 C13 113.2(2)
O1 C12 H12A 109.6(15)
C13 C12 H12A 113.3(15)
O1 C12 H12B 107.1(16)
C13 C12 H12B 108.3(16)
H12A C12 H12B 105(2)
C12 C13 C14 111.9(2)
C12 C13 H13A 107.3(19)
C14 C13 H13A 106.5(18)
C12 C13 H13B 112.8(18)
C14 C13 H13B 105.6(18)
H13A C13 H13B 113(3)
O2 C14 C13 114.7(2)
O2 C14 H14A 106.8(16)
C13 C14 H14A 115.8(16)
O2 C14 H14B 109.4(17)
C13 C14 H14B 101.2(17)
H14A C14 H14B 109(2)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C12 1.396(3)
O1 B1 1.458(3)
O2 C14 1.405(3)
O2 B1 1.476(3)
N1 C1 1.496(2)
N1 C5 1.503(2)
N1 B1 1.641(3)
N1 H1N 0.91(2)
B1 C4 1.610(3)
C1 C2 1.515(3)
C1 H1A 0.99(2)
C1 H1B 0.98(2)
C2 C3 1.521(3)
C2 H2A 0.97(3)
C2 H2B 1.00(2)
C3 C4 1.529(3)
C3 H3A 0.97(2)
C3 H3B 1.00(2)
C4 H4A 0.99(2)
C4 H4B 0.99(2)
C5 C6 1.506(3)
C5 H5A 0.97(2)
C5 H5B 0.98(2)
C6 C7 1.387(3)
C6 C11 1.388(3)
C7 C8 1.388(3)
C7 H7 0.98(3)
C8 C9 1.376(4)
C8 H8 0.93(3)
C9 C10 1.380(4)
C9 H9 0.97(3)
C10 C11 1.380(3)
C10 H10 0.98(3)
C11 H11 0.94(3)
C12 C13 1.467(4)
C12 H12A 0.99(3)
C12 H12B 1.05(3)
C13 C14 1.501(4)
C13 H13A 1.16(4)
C13 H13B 1.00(3)
C14 H14A 0.94(3)
C14 H14B 1.12(3)
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1N O2 0.91(2) 2.07(2) 2.974(2) 172.7(19) 3_676
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
C12 O1 B1 O2 42.2(3)
C12 O1 B1 C4 -89.9(2)
C12 O1 B1 N1 154.00(17)
C14 O2 B1 O1 -37.9(3)
C14 O2 B1 C4 94.4(2)
C14 O2 B1 N1 -149.24(18)
C1 N1 B1 O1 68.41(19)
C5 N1 B1 O1 -56.15(19)
C1 N1 B1 O2 -172.19(16)
C5 N1 B1 O2 63.26(19)
C1 N1 B1 C4 -51.9(2)
C5 N1 B1 C4 -176.44(16)
C5 N1 C1 C2 -179.28(18)
B1 N1 C1 C2 56.3(2)
N1 C1 C2 C3 -60.2(3)
C1 C2 C3 C4 58.7(3)
C2 C3 C4 B1 -57.0(2)
O1 B1 C4 C3 -60.2(2)
O2 B1 C4 C3 167.23(17)
N1 B1 C4 C3 53.1(2)
C1 N1 C5 C6 47.5(2)
B1 N1 C5 C6 171.78(16)
N1 C5 C6 C7 73.2(2)
N1 C5 C6 C11 -105.9(2)
C11 C6 C7 C8 1.5(3)
C5 C6 C7 C8 -177.6(2)
C6 C7 C8 C9 -0.1(3)
C7 C8 C9 C10 -1.2(4)
C8 C9 C10 C11 1.0(4)
C9 C10 C11 C6 0.5(3)
C7 C6 C11 C10 -1.7(3)
C5 C6 C11 C10 177.41(19)
B1 O1 C12 C13 -49.6(3)
O1 C12 C13 C14 50.9(3)
B1 O2 C14 C13 41.4(3)
C12 C13 C14 O2 -47.4(3)
