#------------------------------------------------------------------------------
#$Date: 2019-11-02 07:43:39 +0200 (Sat, 02 Nov 2019) $
#$Revision: 220992 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/12/78/4127820.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_4127820
loop_
_publ_author_name
'Dai, Wen'
'Geib, Steven J.'
'Curran, Dennis P.'
_publ_section_title
;
 Ring-Opening Reactions of NHC-Boriranes with In Situ Generated HCl:
 Synthesis of a New Class of NHC-Boralactones.
;
_journal_issue                   8
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              3623
_journal_page_last               3629
_journal_paper_doi               10.1021/jacs.8b13010
_journal_volume                  141
_journal_year                    2019
_chemical_formula_sum            'C14 H23 B N2 O4'
_chemical_formula_weight         294.15
_space_group_crystal_system      orthorhombic
_space_group_IT_number           29
_space_group_name_Hall           'P 2c -2ac'
_space_group_name_H-M_alt        'P c a 21'
_symmetry_space_group_name_Hall  'P 2c -2ac'
_symmetry_space_group_name_H-M   'P c a 21'
_atom_sites_solution_hydrogens   mixed
_audit_creation_method           SHELXL-2017/1
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.9193(14)
_cell_length_b                   6.1437(4)
_cell_length_c                   14.5047(11)
_cell_measurement_reflns_used    1914
_cell_measurement_temperature    230(2)
_cell_measurement_theta_max      55.815
_cell_measurement_theta_min      4.936
_cell_volume                     1596.8(2)
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2014)'
_diffrn_ambient_temperature      230(2)
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'Bruker Apex II CCD'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0719
_diffrn_reflns_av_unetI/netI     0.0438
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            13746
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.982
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.211
_diffrn_reflns_theta_min         4.936
_diffrn_source                   'Bruker X8 Prospector Ultra Cu IMS'
_exptl_absorpt_coefficient_mu    0.721
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.91
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Bruker Sadabs'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.224
_exptl_crystal_description       blade
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.010
_refine_diff_density_max         0.165
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.034
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.1(4)
_refine_ls_extinction_coef       0.0027(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.462
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         2642
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.461
_refine_ls_R_factor_all          0.0546
_refine_ls_R_factor_gt           0.0418
_refine_ls_shift/su_max          0.036
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+0.0680P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0742
_refine_ls_wR_factor_ref         0.0776
_reflns_Friedel_coverage         0.914
_reflns_Friedel_fraction_full    0.982
_reflns_Friedel_fraction_max     0.981
_reflns_number_gt                2193
_reflns_number_total             2642
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            ja8b13010_si_006.cif
_cod_data_source_block           wendaidb1082a_a
_cod_database_code               4127820
_shelx_shelxl_version_number     2017/1
_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   0.906
_shelx_estimated_absorpt_t_max   0.993
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y, z'
'-x+1/2, y, 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 0.6961(2) 0.4170(6) 0.5376(3) 0.0327(9) Uani 1 1 d . .
H1 H 0.6371(16) 0.361(4) 0.512(2) 0.026(8) Uiso 1 1 d . .
C1 C 0.7587(2) 0.1630(5) 0.6317(3) 0.0393(8) Uani 1 1 d . .
N1 N 0.80909(15) 0.6205(4) 0.45242(18) 0.0329(6) Uani 1 1 d . .
O1 O 0.74344(13) 0.2126(3) 0.54578(16) 0.0415(6) Uani 1 1 d . .
C2 C 0.7188(2) 0.3089(6) 0.6988(2) 0.0399(9) Uani 1 1 d . .
H2A H 0.753(2) 0.341(5) 0.754(3) 0.051(11) Uiso 1 1 d . .
H2B H 0.674(2) 0.218(6) 0.711(3) 0.063(12) Uiso 1 1 d . .
N2 N 0.70018(14) 0.6983(4) 0.39863(17) 0.0334(7) Uani 1 1 d . .
O2 O 0.80065(14) 0.0136(4) 0.6526(2) 0.0567(7) Uani 1 1 d . .
C3 C 0.69733(18) 0.5121(5) 0.6440(2) 0.0319(7) Uani 1 1 d . .
H3 H 0.7341(16) 0.627(5) 0.650(2) 0.030(8) Uiso 1 1 d . .
O3 O 0.57245(14) 0.5052(5) 0.7066(2) 0.0611(8) Uani 1 1 d . .
C4 C 0.6231(2) 0.6019(6) 0.6698(2) 0.0396(8) Uani 1 1 d . .
O4 O 0.61671(14) 0.8123(4) 0.64434(19) 0.0530(7) Uani 1 1 d . .
C5 C 0.5457(2) 0.9134(7) 0.6625(4) 0.0733(14) Uani 1 1 d . .
H5A H 0.542701 1.050700 0.629737 0.110 Uiso 1 1 calc R U
H5B H 0.540581 0.939291 0.728186 0.110 Uiso 1 1 calc R U
H5C H 0.505853 0.818101 0.641871 0.110 Uiso 1 1 calc R U
C6 C 0.73538(18) 0.5770(5) 0.4639(2) 0.0322(7) Uani 1 1 d . .
C7 C 0.8193(2) 0.7639(6) 0.3800(2) 0.0391(8) Uani 1 1 d . .
H7 H 0.870(2) 0.821(6) 0.360(3) 0.061(13) Uiso 1 1 d . .
C8 C 0.7513(2) 0.8121(6) 0.3464(3) 0.0388(9) Uani 1 1 d . .
H8 H 0.734(2) 0.902(6) 0.301(3) 0.050(10) Uiso 1 1 d . .
C9 C 0.8713(2) 0.5237(5) 0.5057(2) 0.0381(8) Uani 1 1 d . .
H9A H 0.850819 0.468451 0.564611 0.046 Uiso 1 1 calc R U
C10 C 0.9028(2) 0.3325(6) 0.4529(3) 0.0572(11) Uani 1 1 d . .
H10A H 0.864040 0.224328 0.443865 0.086 Uiso 1 1 calc R U
H10B H 0.943620 0.268724 0.487532 0.086 Uiso 1 1 calc R U
H10C H 0.920942 0.381689 0.393449 0.086 Uiso 1 1 calc R U
C11 C 0.9294(2) 0.6952(6) 0.5279(3) 0.0535(10) Uani 1 1 d . .
H11A H 0.904973 0.823265 0.552802 0.080 Uiso 1 1 calc R U
H11B H 0.956072 0.734222 0.472066 0.080 Uiso 1 1 calc R U
H11C H 0.964266 0.638008 0.572876 0.080 Uiso 1 1 calc R U
C12 C 0.61828(18) 0.7089(5) 0.3827(2) 0.0406(8) Uani 1 1 d . .
H12A H 0.592807 0.632920 0.434012 0.049 Uiso 1 1 calc R U
C13 C 0.5994(2) 0.5938(8) 0.2939(3) 0.0675(13) Uani 1 1 d . .
H13A H 0.617602 0.445201 0.296461 0.101 Uiso 1 1 calc R U
H13B H 0.622837 0.669105 0.242703 0.101 Uiso 1 1 calc R U
H13C H 0.545747 0.593059 0.285345 0.101 Uiso 1 1 calc R U
C14 C 0.5937(2) 0.9448(6) 0.3827(4) 0.0662(13) Uani 1 1 d . .
H14A H 0.610581 1.014766 0.438916 0.099 Uiso 1 1 calc R U
H14B H 0.539727 0.952010 0.379273 0.099 Uiso 1 1 calc R U
H14C H 0.615165 1.018770 0.329870 0.099 Uiso 1 1 calc R U
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0090 0.0039 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
O1 B1 C6 108.1(3)
O1 B1 C3 102.2(3)
C6 B1 C3 113.5(3)
O1 B1 H1 106.6(13)
C6 B1 H1 111.4(14)
C3 B1 H1 114.1(14)
O2 C1 O1 122.5(3)
O2 C1 C2 125.3(3)
O1 C1 C2 112.2(3)
C6 N1 C7 110.3(3)
C6 N1 C9 126.1(3)
C7 N1 C9 123.5(3)
C1 O1 B1 112.5(3)
C1 C2 C3 105.7(3)
C1 C2 H2A 110(2)
C3 C2 H2A 113(2)
C1 C2 H2B 99(2)
C3 C2 H2B 111(2)
H2A C2 H2B 116(3)
C6 N2 C8 110.6(3)
C6 N2 C12 126.2(3)
C8 N2 C12 123.3(3)
C4 C3 C2 113.4(3)
C4 C3 B1 110.7(3)
C2 C3 B1 101.6(3)
C4 C3 H3 108.3(18)
C2 C3 H3 112.2(18)
B1 C3 H3 110.6(18)
O3 C4 O4 121.9(3)
O3 C4 C3 126.9(3)
O4 C4 C3 111.2(3)
C4 O4 C5 115.9(3)
O4 C5 H5A 109.5
O4 C5 H5B 109.5
H5A C5 H5B 109.5
O4 C5 H5C 109.5
H5A C5 H5C 109.5
H5B C5 H5C 109.5
N2 C6 N1 105.0(3)
N2 C6 B1 126.3(3)
N1 C6 B1 128.7(3)
C8 C7 N1 107.2(3)
C8 C7 H7 129(2)
N1 C7 H7 124(2)
C7 C8 N2 106.9(3)
C7 C8 H8 135(2)
N2 C8 H8 118(2)
N1 C9 C11 110.4(3)
N1 C9 C10 109.2(3)
C11 C9 C10 113.0(3)
N1 C9 H9A 108.0
C11 C9 H9A 108.0
C10 C9 H9A 108.0
C9 C10 H10A 109.5
C9 C10 H10B 109.5
H10A C10 H10B 109.5
C9 C10 H10C 109.5
H10A C10 H10C 109.5
H10B C10 H10C 109.5
C9 C11 H11A 109.5
C9 C11 H11B 109.5
H11A C11 H11B 109.5
C9 C11 H11C 109.5
H11A C11 H11C 109.5
H11B C11 H11C 109.5
N2 C12 C14 109.2(3)
N2 C12 C13 109.5(3)
C14 C12 C13 112.6(3)
N2 C12 H12A 108.5
C14 C12 H12A 108.5
C13 C12 H12A 108.5
C12 C13 H13A 109.5
C12 C13 H13B 109.5
H13A C13 H13B 109.5
C12 C13 H13C 109.5
H13A C13 H13C 109.5
H13B C13 H13C 109.5
C12 C14 H14A 109.5
C12 C14 H14B 109.5
H14A C14 H14B 109.5
C12 C14 H14C 109.5
H14A C14 H14C 109.5
H14B C14 H14C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
B1 O1 1.520(4)
B1 C6 1.614(5)
B1 C3 1.651(5)
B1 H1 1.17(3)
C1 O2 1.225(4)
C1 O1 1.312(4)
C1 C2 1.504(5)
N1 C6 1.358(4)
N1 C7 1.383(4)
N1 C9 1.481(4)
C2 C3 1.529(5)
C2 H2A 1.03(4)
C2 H2B 0.99(4)
N2 C6 1.360(4)
N2 C8 1.380(4)
N2 C12 1.487(4)
C3 C4 1.488(4)
C3 H3 0.97(3)
O3 C4 1.208(4)
C4 O4 1.349(4)
O4 C5 1.441(4)
C5 H5A 0.9700
C5 H5B 0.9700
C5 H5C 0.9700
C7 C8 1.345(5)
C7 H7 1.02(4)
C8 H8 0.91(4)
C9 C11 1.516(5)
C9 C10 1.511(5)
C9 H9A 0.9900
C10 H10A 0.9700
C10 H10B 0.9700
C10 H10C 0.9700
C11 H11A 0.9700
C11 H11B 0.9700
C11 H11C 0.9700
C12 C14 1.515(5)
C12 C13 1.508(5)
C12 H12A 0.9900
C13 H13A 0.9700
C13 H13B 0.9700
C13 H13C 0.9700
C14 H14A 0.9700
C14 H14B 0.9700
C14 H14C 0.9700
