#------------------------------------------------------------------------------
#$Date: 2019-11-24 09:24:30 +0200 (Sun, 24 Nov 2019) $
#$Revision: 237453 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/08/83/4088313.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_4088313
loop_
_publ_author_name
'Lastovickova, Dominika N.'
'Bielawski, Christopher W.'
_publ_section_title
;
 Diamidocarbene Induced B--H Activation: A New Class of Initiator-Free
 Olefin Hydroboration Reagents
;
_journal_issue                   5
_journal_name_full               Organometallics
_journal_page_first              706
_journal_paper_doi               10.1021/acs.organomet.5b00997
_journal_volume                  35
_journal_year                    2016
_chemical_formula_moiety         'C27 H31 B1 Cl3 N2 O2'
_chemical_formula_sum            'C27 H31 B Cl3 N2 O2'
_chemical_formula_weight         532.70
_chemical_name_common            DAC-BCl3
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014
_cell_angle_alpha                102.578(10)
_cell_angle_beta                 108.45(2)
_cell_angle_gamma                97.337(9)
_cell_formula_units_Z            2
_cell_length_a                   9.518(4)
_cell_length_b                   10.870(4)
_cell_length_c                   14.271(5)
_cell_measurement_temperature    150(2)
_cell_volume                     1335.8(9)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_diffrn_ambient_temperature      150(2)
_diffrn_measured_fraction_theta_full 0.967
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Rigaku SCX-Mini with Mercury 2+ CCD'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0804
_diffrn_reflns_av_unetI/netI     0.0661
_diffrn_reflns_Laue_measured_fraction_full 0.967
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            18988
_diffrn_reflns_point_group_measured_fraction_full 0.967
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_min         3.051
_exptl_absorpt_coefficient_mu    0.371
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7095
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Abscor.  T. Higashi (2001). The Rigaku Corporation, Tokyo, Japan.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.324
_exptl_crystal_description       block
_exptl_crystal_F_000             558
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.289
_refine_diff_density_min         -0.315
_refine_diff_density_rms         0.059
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     324
_refine_ls_number_reflns         4680
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.006
_refine_ls_R_factor_all          0.0748
_refine_ls_R_factor_gt           0.0530
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0370P)²+1.3856P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1108
_refine_ls_wR_factor_ref         0.1220
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3612
_reflns_number_total             4680
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            om5b00997_si_002.cif
_cod_data_source_block           DAC-BCl3
_cod_original_cell_volume        1335.7(9)
_cod_database_code               4088313
_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.
;
_shelxl_version_number           2014-3
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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
Cl1 Cl 0.57876(9) -0.00732(7) 0.37430(6) 0.0334(2) Uani 1 1 d . .
N1 N 0.7519(2) 0.2344(2) 0.31571(17) 0.0221(5) Uani 1 1 d . .
O1 O 0.8050(3) 0.4527(2) 0.34097(18) 0.0410(6) Uani 1 1 d . .
C1 C 0.7821(3) 0.1183(3) 0.2825(2) 0.0209(6) Uani 1 1 d . .
B1 B 0.6814(4) -0.0196(3) 0.2851(3) 0.0239(7) Uani 1 1 d . .
Cl2 Cl 0.78759(8) -0.14693(7) 0.30610(6) 0.0314(2) Uani 1 1 d . .
N2 N 0.8814(2) 0.1135(2) 0.23105(17) 0.0219(5) Uani 1 1 d . .
O2 O 1.0459(2) 0.2199(2) 0.17315(17) 0.0348(5) Uani 1 1 d . .
C2 C 0.8053(3) 0.3496(3) 0.2910(2) 0.0270(7) Uani 1 1 d . .
Cl3 Cl 0.54091(9) -0.06433(8) 0.15061(6) 0.0373(2) Uani 1 1 d . .
C3 C 0.8508(3) 0.3263(3) 0.1985(2) 0.0269(7) Uani 1 1 d . .
C4 C 0.7039(4) 0.2757(3) 0.1019(2) 0.0344(8) Uani 1 1 d . .
H4A H 0.6436 0.3402 0.0989 0.052 Uiso 1 1 calc R U
H4B H 0.6471 0.1985 0.1056 0.052 Uiso 1 1 calc R U
H4C H 0.7301 0.2574 0.0414 0.052 Uiso 1 1 calc R U
C5 C 0.9440(4) 0.4492(3) 0.1952(3) 0.0394(8) Uani 1 1 d . .
H5A H 1.0349 0.4778 0.2550 0.059 Uiso 1 1 calc R U
H5B H 0.8857 0.5151 0.1939 0.059 Uiso 1 1 calc R U
H5C H 0.9701 0.4322 0.1346 0.059 Uiso 1 1 calc R U
C6 C 0.9392(3) 0.2212(3) 0.2008(2) 0.0250(7) Uani 1 1 d . .
C7 C 0.9542(3) 0.0051(3) 0.2097(2) 0.0240(6) Uani 1 1 d . .
C8 C 0.9093(3) -0.0725(3) 0.1092(2) 0.0267(7) Uani 1 1 d . .
C9 C 0.9878(4) -0.1698(3) 0.0918(2) 0.0323(7) Uani 1 1 d . .
H9A H 0.9576 -0.2251 0.0260 0.039 Uiso 1 1 calc R U
C10 C 1.1087(3) -0.1873(3) 0.1686(2) 0.0302(7) Uani 1 1 d . .
C11 C 1.1543(3) -0.1028(3) 0.2657(2) 0.0289(7) Uani 1 1 d . .
H11A H 1.2379 -0.1116 0.3174 0.035 Uiso 1 1 calc R U
C12 C 1.0794(3) -0.0055(3) 0.2884(2) 0.0247(7) Uani 1 1 d . .
C13 C 1.1321(3) 0.0834(3) 0.3953(2) 0.0326(8) Uani 1 1 d . .
H13A H 1.1280 0.1701 0.3917 0.049 Uiso 1 1 calc R U
H13B H 1.2344 0.0796 0.4321 0.049 Uiso 1 1 calc R U
H13C H 1.0676 0.0572 0.4304 0.049 Uiso 1 1 calc R U
C14 C 1.1928(4) -0.2925(3) 0.1467(3) 0.0407(9) Uani 1 1 d . .
H14A H 1.2026 -0.3404 0.1967 0.061 Uiso 1 1 calc R U
H14B H 1.2918 -0.2546 0.1501 0.061 Uiso 1 1 calc R U
H14C H 1.1376 -0.3494 0.0793 0.061 Uiso 1 1 calc R U
C15 C 0.7875(4) -0.0537(3) 0.0199(2) 0.0370(8) Uani 1 1 d . .
H15A H 0.8283 -0.0416 -0.0317 0.056 Uiso 1 1 calc R U
H15B H 0.7502 0.0210 0.0427 0.056 Uiso 1 1 calc R U
H15C H 0.7060 -0.1283 -0.0084 0.056 Uiso 1 1 calc R U
C16 C 0.6749(3) 0.2640(3) 0.3900(2) 0.0242(7) Uani 1 1 d . .
C17 C 0.5271(3) 0.2808(3) 0.3544(2) 0.0270(7) Uani 1 1 d . .
C18 C 0.4606(4) 0.3169(3) 0.4269(3) 0.0332(8) Uani 1 1 d . .
H18A H 0.3614 0.3283 0.4049 0.040 Uiso 1 1 calc R U
C19 C 0.5374(4) 0.3365(3) 0.5308(3) 0.0336(8) Uani 1 1 d . .
C20 C 0.6857(4) 0.3209(3) 0.5620(2) 0.0335(8) Uani 1 1 d . .
H20A H 0.7387 0.3346 0.6317 0.040 Uiso 1 1 calc R U
C21 C 0.7586(3) 0.2854(3) 0.4931(2) 0.0277(7) Uani 1 1 d . .
C22 C 0.9185(4) 0.2671(3) 0.5305(2) 0.0387(8) Uani 1 1 d . .
H22A H 0.9583 0.2930 0.6043 0.058 Uiso 1 1 calc R U
H22B H 0.9795 0.3186 0.5051 0.058 Uiso 1 1 calc R U
H22C H 0.9199 0.1778 0.5061 0.058 Uiso 1 1 calc R U
C23 C 0.4606(5) 0.3718(4) 0.6081(3) 0.0484(10) Uani 1 1 d . .
H23A H 0.5332 0.4293 0.6707 0.073 Uiso 1 1 calc R U
H23B H 0.4199 0.2950 0.6218 0.073 Uiso 1 1 calc R U
H23C H 0.3800 0.4134 0.5808 0.073 Uiso 1 1 calc R U
C24 C 0.4403(4) 0.2585(4) 0.2426(2) 0.0395(8) Uani 1 1 d . .
H24A H 0.3362 0.2614 0.2325 0.059 Uiso 1 1 calc R U
H24B H 0.4458 0.1755 0.2052 0.059 Uiso 1 1 calc R U
H24C H 0.4830 0.3244 0.2182 0.059 Uiso 1 1 calc R U
C25 C 0.5147(4) 0.5719(3) 0.0959(2) 0.0359(8) Uani 1 1 d . .
H25A H 0.5242 0.6202 0.1608 0.043 Uiso 1 1 calc R U
C26 C 0.3944(4) 0.4695(3) 0.0425(3) 0.0362(8) Uani 1 1 d . .
H26A H 0.3227 0.4491 0.0714 0.043 Uiso 1 1 calc R U
C27 C 0.3788(4) 0.3966(3) -0.0538(3) 0.0349(8) Uani 1 1 d . .
H27A H 0.2973 0.3271 -0.0897 0.042 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 0.0033 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'
Cl Cl 0.1484 0.1585 '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
C1 N1 C2 124.0(2) . .
C1 N1 C16 124.7(2) . .
C2 N1 C16 111.0(2) . .
N1 C1 N2 117.1(2) . .
N1 C1 B1 122.1(2) . .
N2 C1 B1 120.0(2) . .
C1 B1 Cl1 117.5(2) . .
C1 B1 Cl2 115.4(2) . .
Cl1 B1 Cl2 105.89(17) . .
C1 B1 Cl3 97.94(19) . .
Cl1 B1 Cl3 108.80(17) . .
Cl2 B1 Cl3 110.99(18) . .
C1 N2 C6 123.2(2) . .
C1 N2 C7 124.9(2) . .
C6 N2 C7 111.5(2) . .
O1 C2 N1 119.8(3) . .
O1 C2 C3 125.1(3) . .
N1 C2 C3 115.0(3) . .
C2 C3 C6 108.7(2) . .
C2 C3 C5 111.1(3) . .
C6 C3 C5 110.8(3) . .
C2 C3 C4 107.8(2) . .
C6 C3 C4 107.4(2) . .
C5 C3 C4 110.9(3) . .
C3 C4 H4A 109.5 . .
C3 C4 H4B 109.5 . .
H4A C4 H4B 109.5 . .
C3 C4 H4C 109.5 . .
H4A C4 H4C 109.5 . .
H4B C4 H4C 109.5 . .
C3 C5 H5A 109.5 . .
C3 C5 H5B 109.5 . .
H5A C5 H5B 109.5 . .
C3 C5 H5C 109.5 . .
H5A C5 H5C 109.5 . .
H5B C5 H5C 109.5 . .
O2 C6 N2 120.2(3) . .
O2 C6 C3 123.8(3) . .
N2 C6 C3 115.8(2) . .
C12 C7 C8 122.3(3) . .
C12 C7 N2 118.0(2) . .
C8 C7 N2 119.1(3) . .
C7 C8 C9 117.0(3) . .
C7 C8 C15 124.0(3) . .
C9 C8 C15 119.0(3) . .
C10 C9 C8 122.5(3) . .
C10 C9 H9A 118.7 . .
C8 C9 H9A 118.7 . .
C9 C10 C11 118.1(3) . .
C9 C10 C14 121.1(3) . .
C11 C10 C14 120.7(3) . .
C10 C11 C12 122.1(3) . .
C10 C11 H11A 118.9 . .
C12 C11 H11A 118.9 . .
C11 C12 C7 117.7(3) . .
C11 C12 C13 120.3(3) . .
C7 C12 C13 122.0(3) . .
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 . .
C10 C14 H14A 109.5 . .
C10 C14 H14B 109.5 . .
H14A C14 H14B 109.5 . .
C10 C14 H14C 109.5 . .
H14A C14 H14C 109.5 . .
H14B C14 H14C 109.5 . .
C8 C15 H15A 109.5 . .
C8 C15 H15B 109.5 . .
H15A C15 H15B 109.5 . .
C8 C15 H15C 109.5 . .
H15A C15 H15C 109.5 . .
H15B C15 H15C 109.5 . .
C21 C16 C17 123.2(3) . .
C21 C16 N1 118.0(2) . .
C17 C16 N1 118.4(2) . .
C16 C17 C18 117.3(3) . .
C16 C17 C24 122.0(3) . .
C18 C17 C24 120.7(3) . .
C19 C18 C17 122.0(3) . .
C19 C18 H18A 119.0 . .
C17 C18 H18A 119.0 . .
C18 C19 C20 118.0(3) . .
C18 C19 C23 121.0(3) . .
C20 C19 C23 120.9(3) . .
C19 C20 C21 122.5(3) . .
C19 C20 H20A 118.7 . .
C21 C20 H20A 118.7 . .
C16 C21 C20 116.8(3) . .
C16 C21 C22 122.7(3) . .
C20 C21 C22 120.5(3) . .
C21 C22 H22A 109.5 . .
C21 C22 H22B 109.5 . .
H22A C22 H22B 109.5 . .
C21 C22 H22C 109.5 . .
H22A C22 H22C 109.5 . .
H22B C22 H22C 109.5 . .
C19 C23 H23A 109.5 . .
C19 C23 H23B 109.5 . .
H23A C23 H23B 109.5 . .
C19 C23 H23C 109.5 . .
H23A C23 H23C 109.5 . .
H23B C23 H23C 109.5 . .
C17 C24 H24A 109.5 . .
C17 C24 H24B 109.5 . .
H24A C24 H24B 109.5 . .
C17 C24 H24C 109.5 . .
H24A C24 H24C 109.5 . .
H24B C24 H24C 109.5 . .
C26 C25 C27 120.2(3) . 2_665
C26 C25 H25A 119.9 . .
C27 C25 H25A 119.9 2_665 .
C25 C26 C27 120.6(3) . .
C25 C26 H26A 119.7 . .
C27 C26 H26A 119.7 . .
C25 C27 C26 119.1(3) 2_665 .
C25 C27 H27A 120.4 2_665 .
C26 C27 H27A 120.4 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl1 B1 1.828(3) .
N1 C1 1.349(4) .
N1 C2 1.446(4) .
N1 C16 1.472(4) .
O1 C2 1.191(4) .
C1 N2 1.368(3) .
C1 B1 1.687(4) .
B1 Cl2 1.837(3) .
B1 Cl3 1.874(3) .
N2 C6 1.437(4) .
N2 C7 1.465(4) .
O2 C6 1.201(3) .
C2 C3 1.497(4) .
C3 C6 1.503(4) .
C3 C5 1.526(4) .
C3 C4 1.553(4) .
C4 H4A 0.9600 .
C4 H4B 0.9600 .
C4 H4C 0.9600 .
C5 H5A 0.9600 .
C5 H5B 0.9600 .
C5 H5C 0.9600 .
C7 C12 1.392(4) .
C7 C8 1.394(4) .
C8 C9 1.395(4) .
C8 C15 1.500(4) .
C9 C10 1.382(4) .
C9 H9A 0.9300 .
C10 C11 1.384(4) .
C10 C14 1.511(4) .
C11 C12 1.386(4) .
C11 H11A 0.9300 .
C12 C13 1.504(4) .
C13 H13A 0.9600 .
C13 H13B 0.9600 .
C13 H13C 0.9600 .
C14 H14A 0.9600 .
C14 H14B 0.9600 .
C14 H14C 0.9600 .
C15 H15A 0.9600 .
C15 H15B 0.9600 .
C15 H15C 0.9600 .
C16 C21 1.383(4) .
C16 C17 1.387(4) .
C17 C18 1.387(4) .
C17 C24 1.495(4) .
C18 C19 1.384(5) .
C18 H18A 0.9300 .
C19 C20 1.384(5) .
C19 C23 1.515(4) .
C20 C21 1.390(4) .
C20 H20A 0.9300 .
C21 C22 1.500(4) .
C22 H22A 0.9600 .
C22 H22B 0.9600 .
C22 H22C 0.9600 .
C23 H23A 0.9600 .
C23 H23B 0.9600 .
C23 H23C 0.9600 .
C24 H24A 0.9600 .
C24 H24B 0.9600 .
C24 H24C 0.9600 .
C25 C26 1.372(5) .
C25 C27 1.376(5) 2_665
C25 H25A 0.9300 .
C26 C27 1.380(5) .
C26 H26A 0.9300 .
C27 C25 1.376(5) 2_665
C27 H27A 0.9300 .
