#------------------------------------------------------------------------------
#$Date: 2016-04-05 17:33:35 +0300 (Tue, 05 Apr 2016) $
#$Revision: 181541 $
#$URL: svn://www.crystallography.net/cod/cif/7/11/88/7118850.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_7118850
loop_
_publ_author_name
'Zheng, Junhao'
'Fan, Xiaoting'
'Zhou, Benyu'
'Li, Zhen Hua'
'Wang, Huadong'
_publ_section_title
;
 Tautomerization of 2,6-lutidines in the presence of B(C6F5)3 using
 catecholborane as a precatalyst.
;
_journal_issue                   25
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              4655
_journal_page_last               4658
_journal_paper_doi               10.1039/c6cc00347h
_journal_volume                  52
_journal_year                    2016
_chemical_formula_sum            'C25 H9 B F15 N'
_chemical_formula_weight         619.14
_chemical_name_systematic
; 
 ? 
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2013
_audit_update_record
;
2016-01-05 deposited with the CCDC.
2016-03-07 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 92.675(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.690(5)
_cell_length_b                   18.994(11)
_cell_length_c                   15.963(10)
_cell_measurement_reflns_used    889
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.238
_cell_measurement_theta_min      2.496
_cell_volume                     2329(2)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0408
_diffrn_reflns_av_unetI/netI     0.0457
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            9318
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.998
_diffrn_reflns_theta_min         1.667
_exptl_absorpt_coefficient_mu    0.188
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.694
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.766
_exptl_crystal_description       block
_exptl_crystal_F_000             1224
_exptl_crystal_size_max          1.000
_exptl_crystal_size_mid          0.800
_exptl_crystal_size_min          0.600
_refine_diff_density_max         0.234
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.961
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     384
_refine_ls_number_reflns         4527
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.961
_refine_ls_R_factor_all          0.0781
_refine_ls_R_factor_gt           0.0444
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
; 
 w=1/[σ²(Fo²)+(0.0671P)²] 
 where P=(Fo²+2Fc²)/3 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1081
_refine_ls_wR_factor_ref         0.1219
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2808
_reflns_number_total             4527
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c6cc00347h2.cif
_cod_data_source_block           a50831a
_cod_depositor_comments
'Adding full bibliography for 7118849--7118850.cif.'
_cod_database_code               7118850
_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. 
;
_shelx_estimated_absorpt_t_min   0.835
_shelx_estimated_absorpt_t_max   0.896
_shelxl_version_number           2013-2
loop_
_space_group_symop_operation_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
B1 B 0.4522(3) 0.65866(13) 0.38967(15) 0.0422(6) Uani 1 1 d . .
C1 C 0.6525(3) 0.62392(12) 0.38237(14) 0.0484(6) Uani 1 1 d . .
H1A H 0.7307 0.6454 0.4244 0.058 Uiso 1 1 calc R U
H1B H 0.6477 0.5739 0.3942 0.058 Uiso 1 1 calc R U
C2 C 0.7232(3) 0.63440(11) 0.29844(14) 0.0461(5) Uani 1 1 d . .
C3 C 0.7134(3) 0.58651(13) 0.23278(16) 0.0578(6) Uani 1 1 d . .
H3 H 0.6705 0.5415 0.2415 0.069 Uiso 1 1 calc R U
C4 C 0.7668(3) 0.60530(15) 0.15489(18) 0.0707(8) Uani 1 1 d . .
H4 H 0.7598 0.5727 0.1114 0.085 Uiso 1 1 calc R U
C5 C 0.8308(3) 0.67220(16) 0.14035(16) 0.0654(7) Uani 1 1 d . .
H5 H 0.8626 0.6851 0.0870 0.078 Uiso 1 1 calc R U
C6 C 0.8466(3) 0.71890(13) 0.20523(15) 0.0526(6) Uani 1 1 d . .
C7 C 0.9181(4) 0.79111(15) 0.19905(19) 0.0750(8) Uani 1 1 d . .
H7A H 0.8410 0.8239 0.2241 0.113 Uiso 1 1 calc R U
H7B H 0.9294 0.8031 0.1411 0.113 Uiso 1 1 calc R U
H7C H 1.0304 0.7931 0.2279 0.113 Uiso 1 1 calc R U
C8 C 0.3505(3) 0.63101(12) 0.30204(13) 0.0429(5) Uani 1 1 d . .
C9 C 0.3278(3) 0.66985(13) 0.22911(14) 0.0502(6) Uani 1 1 d . .
C10 C 0.2594(3) 0.64324(15) 0.15425(15) 0.0618(7) Uani 1 1 d . .
C11 C 0.2119(3) 0.57437(16) 0.14834(17) 0.0664(7) Uani 1 1 d . .
C12 C 0.2349(3) 0.53191(14) 0.21750(17) 0.0611(7) Uani 1 1 d . .
C13 C 0.3048(3) 0.56068(12) 0.29094(15) 0.0489(6) Uani 1 1 d . .
C14 C 0.3631(3) 0.63000(11) 0.47576(14) 0.0444(5) Uani 1 1 d . .
C15 C 0.1931(3) 0.60625(11) 0.48178(15) 0.0497(6) Uani 1 1 d . .
C16 C 0.1236(3) 0.58498(12) 0.55581(17) 0.0603(7) Uani 1 1 d . .
C17 C 0.2232(4) 0.58767(13) 0.62903(17) 0.0664(8) Uani 1 1 d . .
C18 C 0.3904(4) 0.61213(14) 0.62786(15) 0.0642(7) Uani 1 1 d . .
C19 C 0.4547(3) 0.63302(13) 0.55268(15) 0.0548(6) Uani 1 1 d . .
C20 C 0.4456(3) 0.74526(12) 0.39951(13) 0.0461(5) Uani 1 1 d . .
C21 C 0.5824(3) 0.79074(13) 0.42169(14) 0.0533(6) Uani 1 1 d . .
C22 C 0.5678(4) 0.86233(14) 0.43010(16) 0.0650(7) Uani 1 1 d . .
C23 C 0.4077(5) 0.89351(14) 0.41675(17) 0.0727(8) Uani 1 1 d . .
C24 C 0.2668(4) 0.85213(15) 0.39754(16) 0.0661(7) Uani 1 1 d . .
C25 C 0.2880(3) 0.78081(12) 0.39035(14) 0.0515(6) Uani 1 1 d . .
F1 F 0.3760(2) 0.73815(8) 0.22729(9) 0.0678(4) Uani 1 1 d . .
F2 F 0.2397(2) 0.68601(10) 0.08650(9) 0.0911(5) Uani 1 1 d . .
F3 F 0.1423(3) 0.54839(11) 0.07583(11) 0.1018(6) Uani 1 1 d . .
F4 F 0.1925(2) 0.46369(9) 0.21349(11) 0.0893(5) Uani 1 1 d . .
F5 F 0.33132(18) 0.51506(7) 0.35553(9) 0.0639(4) Uani 1 1 d . .
F6 F 0.08271(16) 0.60342(8) 0.41372(9) 0.0656(4) Uani 1 1 d . .
F7 F -0.0430(2) 0.56338(9) 0.55644(11) 0.0887(5) Uani 1 1 d . .
F8 F 0.1563(3) 0.56770(9) 0.70189(11) 0.1017(6) Uani 1 1 d . .
F9 F 0.4883(2) 0.61638(10) 0.69953(9) 0.0947(6) Uani 1 1 d . .
F10 F 0.61849(19) 0.65927(9) 0.55717(9) 0.0772(5) Uani 1 1 d . .
F11 F 0.74785(18) 0.76531(8) 0.43640(9) 0.0682(4) Uani 1 1 d . .
F12 F 0.7100(2) 0.90119(8) 0.45063(11) 0.0914(6) Uani 1 1 d . .
F13 F 0.3934(3) 0.96350(9) 0.42338(12) 0.1138(7) Uani 1 1 d . .
F14 F 0.1079(2) 0.88125(9) 0.38637(11) 0.0990(6) Uani 1 1 d . .
F15 F 0.14093(18) 0.74317(8) 0.37202(9) 0.0666(4) Uani 1 1 d . .
N1 N 0.7943(2) 0.69748(11) 0.28107(13) 0.0478(5) Uani 1 1 d . .
H1 H 0.814(4) 0.7276(14) 0.3271(18) 0.079(9) 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'
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
C20 B1 C8 112.37(17)
C20 B1 C14 103.45(17)
C8 B1 C14 113.55(18)
C20 B1 C1 115.36(18)
C8 B1 C1 102.39(17)
C14 B1 C1 110.09(17)
C2 C1 B1 112.63(17)
C2 C1 H1A 109.1
B1 C1 H1A 109.1
C2 C1 H1B 109.1
B1 C1 H1B 109.1
H1A C1 H1B 107.8
N1 C2 C3 115.8(2)
N1 C2 C1 118.3(2)
C3 C2 C1 125.8(2)
C4 C3 C2 120.3(2)
C4 C3 H3 119.8
C2 C3 H3 119.8
C3 C4 C5 120.9(2)
C3 C4 H4 119.6
C5 C4 H4 119.6
C6 C5 C4 119.2(2)
C6 C5 H5 120.4
C4 C5 H5 120.4
N1 C6 C5 117.6(2)
N1 C6 C7 117.6(2)
C5 C6 C7 124.8(2)
C6 C7 H7A 109.5
C6 C7 H7B 109.5
H7A C7 H7B 109.5
C6 C7 H7C 109.5
H7A C7 H7C 109.5
H7B C7 H7C 109.5
C9 C8 C13 112.6(2)
C9 C8 B1 125.3(2)
C13 C8 B1 121.27(19)
F1 C9 C10 115.3(2)
F1 C9 C8 120.5(2)
C10 C9 C8 124.2(2)
F2 C10 C11 120.1(2)
F2 C10 C9 119.7(3)
C11 C10 C9 120.2(2)
F3 C11 C10 120.5(3)
F3 C11 C12 120.5(3)
C10 C11 C12 119.0(2)
F4 C12 C11 120.6(2)
F4 C12 C13 120.6(3)
C11 C12 C13 118.8(3)
F5 C13 C12 115.6(2)
F5 C13 C8 119.3(2)
C12 C13 C8 125.1(2)
C19 C14 C15 113.1(2)
C19 C14 B1 120.5(2)
C15 C14 B1 126.20(19)
F6 C15 C16 115.1(2)
F6 C15 C14 121.1(2)
C16 C15 C14 123.9(2)
F7 C16 C17 120.0(2)
F7 C16 C15 120.2(3)
C17 C16 C15 119.8(3)
F8 C17 C16 120.4(3)
F8 C17 C18 120.3(3)
C16 C17 C18 119.3(2)
F9 C18 C17 119.9(2)
F9 C18 C19 121.0(3)
C17 C18 C19 119.1(2)
F10 C19 C18 115.5(2)
F10 C19 C14 119.6(2)
C18 C19 C14 124.8(3)
C25 C20 C21 111.7(2)
C25 C20 B1 120.25(19)
C21 C20 B1 127.9(2)
F11 C21 C22 114.3(2)
F11 C21 C20 120.6(2)
C22 C21 C20 125.1(2)
F12 C22 C21 119.9(3)
F12 C22 C23 120.9(3)
C21 C22 C23 119.3(3)
F13 C23 C24 121.6(3)
F13 C23 C22 119.5(3)
C24 C23 C22 119.0(2)
F14 C24 C23 120.0(3)
F14 C24 C25 120.4(3)
C23 C24 C25 119.5(3)
F15 C25 C24 115.9(2)
F15 C25 C20 118.7(2)
C24 C25 C20 125.3(2)
C2 N1 C6 126.1(2)
C2 N1 H1 115.7(17)
C6 N1 H1 118.1(17)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
B1 C20 1.653(3)
B1 C8 1.656(3)
B1 C14 1.656(3)
B1 C1 1.685(3)
C1 C2 1.483(3)
C1 H1A 0.9700
C1 H1B 0.9700
C2 N1 1.351(3)
C2 C3 1.387(3)
C3 C4 1.375(4)
C3 H3 0.9300
C4 C5 1.386(4)
C4 H4 0.9300
C5 C6 1.365(4)
C5 H5 0.9300
C6 N1 1.356(3)
C6 C7 1.483(4)
C7 H7A 0.9600
C7 H7B 0.9600
C7 H7C 0.9600
C8 C9 1.383(3)
C8 C13 1.391(3)
C9 F1 1.350(3)
C9 C10 1.379(3)
C10 F2 1.355(3)
C10 C11 1.360(4)
C11 F3 1.346(3)
C11 C12 1.372(4)
C12 F4 1.337(3)
C12 C13 1.379(3)
C13 F5 1.355(3)
C14 C19 1.388(3)
C14 C15 1.391(3)
C15 F6 1.348(3)
C15 C16 1.380(3)
C16 F7 1.345(3)
C16 C17 1.368(4)
C17 F8 1.348(3)
C17 C18 1.368(4)
C18 F9 1.342(3)
C18 C19 1.377(4)
C19 F10 1.353(3)
C20 C25 1.389(3)
C20 C21 1.394(3)
C21 F11 1.371(3)
C21 C22 1.372(4)
C22 F12 1.347(3)
C22 C23 1.374(4)
C23 F13 1.339(3)
C23 C24 1.362(4)
C24 F14 1.345(3)
C24 C25 1.370(4)
C25 F15 1.358(3)
N1 H1 0.94(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
N1 H1 F11 0.94(3) 1.98(3) 2.832(3) 151(2)
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
C20 B1 C1 C2 -76.2(2)
C8 B1 C1 C2 46.1(2)
C14 B1 C1 C2 167.18(18)
B1 C1 C2 N1 80.4(2)
B1 C1 C2 C3 -95.1(3)
N1 C2 C3 C4 -2.9(3)
C1 C2 C3 C4 172.8(2)
C2 C3 C4 C5 -0.1(4)
C3 C4 C5 C6 2.4(4)
C4 C5 C6 N1 -1.5(4)
C4 C5 C6 C7 178.0(3)
C20 B1 C8 C9 26.7(3)
C14 B1 C8 C9 143.7(2)
C1 B1 C8 C9 -97.7(2)
C20 B1 C8 C13 -164.48(19)
C14 B1 C8 C13 -47.5(3)
C1 B1 C8 C13 71.1(2)
C13 C8 C9 F1 -175.90(18)
B1 C8 C9 F1 -6.2(3)
C13 C8 C9 C10 3.0(3)
B1 C8 C9 C10 172.7(2)
F1 C9 C10 F2 -2.1(3)
C8 C9 C10 F2 178.9(2)
F1 C9 C10 C11 177.8(2)
C8 C9 C10 C11 -1.1(4)
F2 C10 C11 F3 -1.2(4)
C9 C10 C11 F3 178.8(2)
F2 C10 C11 C12 179.3(2)
C9 C10 C11 C12 -0.7(4)
F3 C11 C12 F4 1.6(4)
C10 C11 C12 F4 -178.8(2)
F3 C11 C12 C13 -179.2(2)
C10 C11 C12 C13 0.3(4)
F4 C12 C13 F5 2.1(3)
C11 C12 C13 F5 -177.1(2)
F4 C12 C13 C8 -178.9(2)
C11 C12 C13 C8 2.0(4)
C9 C8 C13 F5 175.51(18)
B1 C8 C13 F5 5.4(3)
C9 C8 C13 C12 -3.5(3)
B1 C8 C13 C12 -173.6(2)
C20 B1 C14 C19 -74.3(2)
C8 B1 C14 C19 163.64(19)
C1 B1 C14 C19 49.5(3)
C20 B1 C14 C15 100.7(2)
C8 B1 C14 C15 -21.4(3)
C1 B1 C14 C15 -135.5(2)
C19 C14 C15 F6 176.61(19)
B1 C14 C15 F6 1.3(3)
C19 C14 C15 C16 -2.5(3)
B1 C14 C15 C16 -177.8(2)
F6 C15 C16 F7 0.1(3)
C14 C15 C16 F7 179.3(2)
F6 C15 C16 C17 -178.2(2)
C14 C15 C16 C17 1.0(4)
F7 C16 C17 F8 1.1(4)
C15 C16 C17 F8 179.4(2)
F7 C16 C17 C18 -177.7(2)
C15 C16 C17 C18 0.6(4)
F8 C17 C18 F9 -0.1(4)
C16 C17 C18 F9 178.6(2)
F8 C17 C18 C19 -179.2(2)
C16 C17 C18 C19 -0.4(4)
F9 C18 C19 F10 -1.7(3)
C17 C18 C19 F10 177.4(2)
F9 C18 C19 C14 179.6(2)
C17 C18 C19 C14 -1.4(4)
C15 C14 C19 F10 -176.0(2)
B1 C14 C19 F10 -0.4(3)
C15 C14 C19 C18 2.7(3)
B1 C14 C19 C18 178.3(2)
C8 B1 C20 C25 51.1(3)
C14 B1 C20 C25 -71.8(2)
C1 B1 C20 C25 167.94(19)
C8 B1 C20 C21 -133.1(2)
C14 B1 C20 C21 104.1(2)
C1 B1 C20 C21 -16.2(3)
C25 C20 C21 F11 177.82(19)
B1 C20 C21 F11 1.7(3)
C25 C20 C21 C22 -2.8(3)
B1 C20 C21 C22 -178.9(2)
F11 C21 C22 F12 0.5(3)
C20 C21 C22 F12 -179.0(2)
F11 C21 C22 C23 180.0(2)
C20 C21 C22 C23 0.5(4)
F12 C22 C23 F13 0.7(4)
C21 C22 C23 F13 -178.8(2)
F12 C22 C23 C24 -178.9(2)
C21 C22 C23 C24 1.6(4)
F13 C23 C24 F14 -1.3(4)
C22 C23 C24 F14 178.2(2)
F13 C23 C24 C25 179.2(2)
C22 C23 C24 C25 -1.3(4)
F14 C24 C25 F15 -0.2(3)
C23 C24 C25 F15 179.3(2)
F14 C24 C25 C20 179.2(2)
C23 C24 C25 C20 -1.3(4)
C21 C20 C25 F15 -177.44(19)
B1 C20 C25 F15 -1.0(3)
C21 C20 C25 C24 3.2(3)
B1 C20 C25 C24 179.7(2)
C3 C2 N1 C6 4.0(3)
C1 C2 N1 C6 -171.97(19)
C5 C6 N1 C2 -1.8(3)
C7 C6 N1 C2 178.7(2)
