#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/87/1518757.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_1518757
loop_
_publ_author_name
'Kong, Lingbing'
'Ganguly, Rakesh'
'Li, Yongxin'
'Kinjo, Rei'
_publ_section_title
;
 Diverse reactivity of a tricoordinate organoboron L2PhB: (L =
 oxazol-2-ylidene) towards alkali metal, group 9 metal, and coinage metal
 precursors
;
_journal_issue                   5
_journal_name_full               'Chem. Sci.'
_journal_page_first              2893
_journal_paper_doi               10.1039/C5SC00404G
_journal_volume                  6
_journal_year                    2015
_chemical_formula_sum            'C19 H27 B F3 Li N2 O5 S'
_chemical_formula_weight         470.23
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_audit_update_record
;
2014-12-10 deposited with the CCDC.
2015-02-22 downloaded from the CCDC.
;
_cell_angle_alpha                96.176(5)
_cell_angle_beta                 93.242(5)
_cell_angle_gamma                97.646(6)
_cell_formula_units_Z            2
_cell_length_a                   5.9513(6)
_cell_length_b                   10.9562(11)
_cell_length_c                   17.3953(15)
_cell_measurement_reflns_used    1130
_cell_measurement_temperature    103.(2)
_cell_measurement_theta_max      20.8774
_cell_measurement_theta_min      2.8460
_cell_volume                     1114.73(19)
_computing_cell_refinement       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_collection       'APEX2 (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_molecular_graphics    'XP (Bruker AXS Inc., 2013)'
_computing_publication_material  'APEX2 (Bruker AXS Inc., 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_diffrn_ambient_temperature      103.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1403
_diffrn_reflns_av_unetI/netI     0.1778
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            15655
_diffrn_reflns_theta_full        26.46
_diffrn_reflns_theta_max         26.46
_diffrn_reflns_theta_min         2.36
_diffrn_source                   'fine-focus sealed tube'
_exptl_absorpt_coefficient_mu    0.203
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.98
_exptl_absorpt_process_details
;
;
_exptl_crystal_density_diffrn    1.401
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             492
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.040
_refine_diff_density_max         0.347
_refine_diff_density_min         -0.459
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.996
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     295
_refine_ls_number_reflns         4579
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.996
_refine_ls_R_factor_all          0.1713
_refine_ls_R_factor_gt           0.0685
_refine_ls_shift/su_max          0.009
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0423P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1112
_refine_ls_wR_factor_ref         0.1408
_reflns_number_gt                2263
_reflns_number_total             4579
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c5sc00404g2.cif
_cod_data_source_block           I
_cod_depositor_comments
'Adding full bibliography for 1518755--1518759.cif.'
_cod_database_code               1518757
#BEGIN Tags that were not found in dictionaries:
#END Tags that were not found in dictionaries
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_posn
_atom_site_occupancy
B B1 0.3486(7) 0.3400(4) 0.1788(2) 0.0138(10) Uani d . . 1
C C1 0.2609(6) 0.4548(3) 0.21286(17) 0.0131(9) Uani d . . 1
C C2 0.0773(7) 0.6328(3) 0.23496(18) 0.0142(9) Uani d . . 1
C C3 0.1437(7) 0.5858(3) 0.31098(18) 0.0187(9) Uani d . . 1
H H3A 0.2169 0.6551 0.3493 0.022 Uiso calc U R 1
H H3B 0.0088 0.5434 0.3329 0.022 Uiso calc U R 1
C C4 0.0846(7) 0.5297(4) 0.09739(18) 0.0261(11) Uani d . . 1
H H4A 0.2186 0.5106 0.0707 0.039 Uiso calc U R 1
H H4B 0.0511 0.6118 0.087 0.039 Uiso calc U R 1
H H4C -0.0458 0.4672 0.0786 0.039 Uiso calc U R 1
C C5 -0.1720(6) 0.6477(4) 0.2275(2) 0.0206(10) Uani d . . 1
H H5A -0.2081 0.6763 0.1774 0.031 Uiso calc U R 1
H H5B -0.2046 0.7087 0.2694 0.031 Uiso calc U R 1
H H5C -0.2646 0.5678 0.231 0.031 Uiso calc U R 1
C C6 0.2290(7) 0.7528(3) 0.2246(2) 0.0216(10) Uani d . . 1
H H6A 0.3888 0.7418 0.2335 0.032 Uiso calc U R 1
H H6B 0.1939 0.82 0.2619 0.032 Uiso calc U R 1
H H6C 0.2018 0.7735 0.1718 0.032 Uiso calc U R 1
C C7 0.5113(6) 0.2841(3) 0.22842(18) 0.0130(9) Uani d . . 1
C C8 0.7189(7) 0.1473(3) 0.29020(18) 0.0166(9) Uani d . . 1
C C9 0.7958(7) 0.2800(3) 0.3235(2) 0.0196(10) Uani d . . 1
H H9A 0.8163 0.2876 0.3807 0.024 Uiso calc U R 1
H H9B 0.9406 0.3127 0.3029 0.024 Uiso calc U R 1
C C10 0.4897(7) 0.0698(3) 0.16243(19) 0.0206(10) Uani d . . 1
H H10A 0.325 0.0583 0.1669 0.031 Uiso calc U R 1
H H10B 0.5507 -0.0058 0.1734 0.031 Uiso calc U R 1
H H10C 0.5219 0.0873 0.1098 0.031 Uiso calc U R 1
C C11 0.9176(7) 0.0779(4) 0.2729(2) 0.0243(10) Uani d . . 1
H H11A 0.8606 -0.0059 0.2481 0.036 Uiso calc U R 1
H H11B 1.0062 0.0728 0.3214 0.036 Uiso calc U R 1
H H11C 1.0145 0.122 0.2381 0.036 Uiso calc U R 1
C C12 0.5544(7) 0.0812(4) 0.34109(19) 0.0226(10) Uani d . . 1
H H12A 0.4325 0.131 0.3522 0.034 Uiso calc U R 1
H H12B 0.6358 0.0699 0.3898 0.034 Uiso calc U R 1
H H12C 0.489 0 0.3141 0.034 Uiso calc U R 1
C C13 0.2676(7) 0.2773(3) 0.09364(18) 0.0141(9) Uani d . . 1
C C14 0.4180(7) 0.2709(3) 0.03485(19) 0.0187(9) Uani d . . 1
H H14 0.5705 0.3101 0.0456 0.022 Uiso calc U R 1
C C15 0.3525(7) 0.2093(4) -0.03884(19) 0.0220(10) Uani d . . 1
H H15 0.4591 0.2074 -0.0774 0.026 Uiso calc U R 1
C C16 0.1322(7) 0.1510(4) -0.05565(19) 0.0211(10) Uani d . . 1
H H16 0.0876 0.1069 -0.1054 0.025 Uiso calc U R 1
C C17 -0.0229(7) 0.1571(3) 0.00016(19) 0.0201(9) Uani d . . 1
H H17 -0.1755 0.1186 -0.0114 0.024 Uiso calc U R 1
C C18 0.0449(7) 0.2199(3) 0.07349(19) 0.0169(9) Uani d . . 1
H H18 -0.0642 0.2238 0.1112 0.02 Uiso calc U R 1
C C19 0.7520(11) 0.8161(4) 0.4682(2) 0.0440(15) Uani d . . 1
F F1 0.8454(6) 0.8433(2) 0.40239(13) 0.0675(10) Uani d . . 1
F F2 0.5312(6) 0.8245(3) 0.45993(15) 0.0624(9) Uani d . . 1
F F3 0.8465(6) 0.9005(2) 0.52499(14) 0.0688(10) Uani d . . 1
Li Li1 0.4749(12) 0.4462(6) 0.3748(3) 0.0229(16) Uani d . . 1
N N1 0.1293(6) 0.5288(3) 0.18061(15) 0.0178(8) Uani d . . 1
N N2 0.5958(5) 0.1732(3) 0.21776(14) 0.0141(7) Uani d . . 1
O O1 0.3011(4) 0.5003(2) 0.29095(11) 0.0151(6) Uani d . . 1
O O2 0.6137(4) 0.3452(2) 0.29866(12) 0.0151(6) Uani d . . 1
O O3 0.6739(5) 0.5839(2) 0.42286(13) 0.0259(7) Uani d . . 1
O O4 0.7036(5) 0.6508(2) 0.56120(12) 0.0262(7) Uani d . . 1
O O5 1.0425(5) 0.6650(3) 0.48933(14) 0.0467(9) Uani d . . 1
S S1 0.8006(2) 0.66072(10) 0.48759(5) 0.0261(3) Uani d . . 1
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'
S S 0.1246 0.1234 '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'
Li Li -0.0003 0.0001 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
C7 B1 C1 . . 118.0(3)
C7 B1 C13 . . 120.6(3)
C1 B1 C13 . . 121.4(3)
N1 C1 O1 . . 106.8(3)
N1 C1 B1 . . 130.8(3)
O1 C1 B1 . . 122.4(3)
N1 C2 C5 . . 111.8(3)
N1 C2 C3 . . 99.0(3)
C5 C2 C3 . . 112.2(3)
N1 C2 C6 . . 110.8(3)
C5 C2 C6 . . 111.6(3)
C3 C2 C6 . . 110.8(3)
O1 C3 C2 . . 104.7(2)
O1 C3 H3A . . 110.8
C2 C3 H3A . . 110.8
O1 C3 H3B . . 110.8
C2 C3 H3B . . 110.8
H3A C3 H3B . . 108.9
N1 C4 H4A . . 109.5
N1 C4 H4B . . 109.5
H4A C4 H4B . . 109.5
N1 C4 H4C . . 109.5
H4A C4 H4C . . 109.5
H4B C4 H4C . . 109.5
C2 C5 H5A . . 109.5
C2 C5 H5B . . 109.5
H5A C5 H5B . . 109.5
C2 C5 H5C . . 109.5
H5A C5 H5C . . 109.5
H5B C5 H5C . . 109.5
C2 C6 H6A . . 109.5
C2 C6 H6B . . 109.5
H6A C6 H6B . . 109.5
C2 C6 H6C . . 109.5
H6A C6 H6C . . 109.5
H6B C6 H6C . . 109.5
N2 C7 O2 . . 106.2(3)
N2 C7 B1 . . 131.3(3)
O2 C7 B1 . . 122.5(3)
N2 C8 C9 . . 97.4(3)
N2 C8 C11 . . 111.9(3)
C9 C8 C11 . . 112.1(3)
N2 C8 C12 . . 110.5(3)
C9 C8 C12 . . 111.5(3)
C11 C8 C12 . . 112.6(3)
O2 C9 C8 . . 104.1(3)
O2 C9 H9A . . 110.9
C8 C9 H9A . . 110.9
O2 C9 H9B . . 110.9
C8 C9 H9B . . 110.9
H9A C9 H9B . . 109.0
N2 C10 H10A . . 109.5
N2 C10 H10B . . 109.5
H10A C10 H10B . . 109.5
N2 C10 H10C . . 109.5
H10A C10 H10C . . 109.5
H10B C10 H10C . . 109.5
C8 C11 H11A . . 109.5
C8 C11 H11B . . 109.5
H11A C11 H11B . . 109.5
C8 C11 H11C . . 109.5
H11A C11 H11C . . 109.5
H11B C11 H11C . . 109.5
C8 C12 H12A . . 109.5
C8 C12 H12B . . 109.5
H12A C12 H12B . . 109.5
C8 C12 H12C . . 109.5
H12A C12 H12C . . 109.5
H12B C12 H12C . . 109.5
C18 C13 C14 . . 115.8(3)
C18 C13 B1 . . 122.3(3)
C14 C13 B1 . . 121.8(3)
C15 C14 C13 . . 122.4(4)
C15 C14 H14 . . 118.8
C13 C14 H14 . . 118.8
C16 C15 C14 . . 119.8(3)
C16 C15 H15 . . 120.1
C14 C15 H15 . . 120.1
C17 C16 C15 . . 119.6(3)
C17 C16 H16 . . 120.2
C15 C16 H16 . . 120.2
C16 C17 C18 . . 119.8(4)
C16 C17 H17 . . 120.1
C18 C17 H17 . . 120.1
C17 C18 C13 . . 122.4(3)
C17 C18 H18 . . 118.8
C13 C18 H18 . . 118.8
F3 C19 F2 . . 108.5(4)
F3 C19 F1 . . 107.9(4)
F2 C19 F1 . . 108.2(4)
F3 C19 S1 . . 110.9(4)
F2 C19 S1 . . 111.4(3)
F1 C19 S1 . . 109.7(3)
O3 Li1 O4 . 2_666 117.8(3)
O3 Li1 O2 . . 113.2(4)
O4 Li1 O2 2_666 . 112.0(3)
O3 Li1 O1 . . 107.8(3)
O4 Li1 O1 2_666 . 113.8(4)
O2 Li1 O1 . . 88.4(2)
C1 N1 C4 . . 124.6(3)
C1 N1 C2 . . 114.0(3)
C4 N1 C2 . . 119.8(3)
C7 N2 C10 . . 122.8(3)
C7 N2 C8 . . 111.4(3)
C10 N2 C8 . . 119.2(3)
C1 O1 C3 . . 109.2(3)
C1 O1 Li1 . . 131.8(3)
C3 O1 Li1 . . 117.6(2)
C7 O2 C9 . . 108.6(3)
C7 O2 Li1 . . 126.8(3)
C9 O2 Li1 . . 119.3(3)
S1 O3 Li1 . . 155.1(2)
S1 O4 Li1 . 2_666 148.5(3)
O5 S1 O3 . . 115.60(17)
O5 S1 O4 . . 115.27(16)
O3 S1 O4 . . 114.74(16)
O5 S1 C19 . . 104.3(2)
O3 S1 C19 . . 102.1(2)
O4 S1 C19 . . 102.10(18)
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
B1 C7 . 1.495(5)
B1 C1 . 1.502(5)
B1 C13 . 1.584(5)
C1 N1 . 1.343(4)
C1 O1 . 1.392(4)
C2 N1 . 1.478(4)
C2 C5 . 1.513(5)
C2 C3 . 1.520(5)
C2 C6 . 1.526(5)
C3 O1 . 1.441(4)
C3 H3A . 0.99
C3 H3B . 0.99
C4 N1 . 1.458(4)
C4 H4A . 0.98
C4 H4B . 0.98
C4 H4C . 0.98
C5 H5A . 0.98
C5 H5B . 0.98
C5 H5C . 0.98
C6 H6A . 0.98
C6 H6B . 0.98
C6 H6C . 0.98
C7 N2 . 1.374(4)
C7 O2 . 1.394(4)
C8 N2 . 1.494(4)
C8 C9 . 1.507(5)
C8 C11 . 1.515(5)
C8 C12 . 1.521(5)
C9 O2 . 1.446(4)
C9 H9A . 0.99
C9 H9B . 0.99
C10 N2 . 1.454(4)
C10 H10A . 0.98
C10 H10B . 0.98
C10 H10C . 0.98
C11 H11A . 0.98
C11 H11B . 0.98
C11 H11C . 0.98
C12 H12A . 0.98
C12 H12B . 0.98
C12 H12C . 0.98
C13 C18 . 1.398(5)
C13 C14 . 1.399(5)
C14 C15 . 1.392(5)
C14 H14 . 0.95
C15 C16 . 1.381(5)
C15 H15 . 0.95
C16 C17 . 1.379(5)
C16 H16 . 0.95
C17 C18 . 1.394(5)
C17 H17 . 0.95
C18 H18 . 0.95
C19 F3 . 1.323(5)
C19 F2 . 1.330(6)
C19 F1 . 1.344(4)
C19 S1 . 1.828(5)
Li1 O3 . 1.876(7)
Li1 O4 2_666 1.894(7)
Li1 O2 . 1.926(6)
Li1 O1 . 1.931(7)
O3 S1 . 1.441(3)
O4 S1 . 1.443(2)
O4 Li1 2_666 1.894(7)
O5 S1 . 1.433(3)
