Reactions of BICAAC with hydroboranes: propensity for Lewis adduct formation and carbene insertion into B-H bond
Manar, Krishna Kumar; porwal, vishal kumar; Kamte, Rohit S.; Adhikari, Manu; Thakur, Sandeep Kumar; Bawari, Deependra; Roychoudhury, Angshuman; Singh, Sanjay; Dalton Transactions  (2019) –; doi:10.1039/C9DT03382C

data_7701416
_publ_section_title
;
 Reactions of BICAAC with hydroboranes: propensity for Lewis adduct
 formation and carbene insertion into B-H bond
;
_journal_name_full               'Dalton Transactions'
_journal_paper_doi               10.1039/C9DT03382C
_journal_year                    2019
_chemical_formula_moiety         '2(C22 H35 B Cl N)'
_chemical_formula_sum            'C44 H70 B2 Cl2 N2'
_chemical_formula_weight         719.54
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_Hall           '-P 2ac 2ab'
_space_group_name_H-M_alt        'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2019-06-19
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-06-20 deposited with the CCDC.    2019-10-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   15.3620(11)
_cell_length_b                   18.1323(12)
_cell_length_c                   30.142(2)
_cell_measurement_reflns_used    1818
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      18.56
_cell_measurement_theta_min      2.62
_cell_volume                     8396.0(10)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.0
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.1347
_diffrn_reflns_av_unetI/netI     0.1360
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            36531
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.064
_diffrn_reflns_theta_max         25.064
_diffrn_reflns_theta_min         1.351
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.187
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_correction_T_min  0.6374
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0707 before and 0.0652 after correction. The Ratio of minimum to maximum transmission is 0.8553. The \l/2 correction factor is 0.00150.'
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.138
_exptl_crystal_description       block
_exptl_crystal_F_000             3136
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         1.100
_refine_diff_density_min         -0.558
_refine_diff_density_rms         0.069
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     490
_refine_ls_number_reflns         7419
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.045
_refine_ls_R_factor_all          0.1913
_refine_ls_R_factor_gt           0.0862
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1192P)^2^+3.0269P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2082
_refine_ls_wR_factor_ref         0.2616
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3492
_reflns_number_total             7419
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9dt03382c2.cif
_cod_data_source_block           Compound3-100k_0m_a
_cod_database_code               7701416
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.964
_shelx_estimated_absorpt_t_min   0.955
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All B(H,H) groups, All C(H) groups, All C(H,H) groups, All C(H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Shared sites
{B2A, B2B}
{B1A, B1B}
{C7A, C7B}
{C3A, C3B}
3. Uiso/Uaniso restraints and constraints
Uanis(B2A) = Uanis(B2B)
Uanis(Cl2A) = Uanis(Cl2B)
Uanis(B1A) = Uanis(B1B)
Uanis(C7A) = Uanis(C7B)
Uanis(C3A) = Uanis(C3B)
4. Others
 Sof(Cl2B)=Sof(B2B)=Sof(H2BA)=Sof(H2BB)=1-FVAR(1)
 Sof(Cl2A)=Sof(B2A)=Sof(H2AA)=Sof(H2AB)=FVAR(1)
 Sof(C3B)=Sof(H3BA)=Sof(H3BB)=Sof(H6BC)=Sof(H6BD)=Sof(H4BC)=Sof(H4BD)=Sof(C7B)=
 Sof(H7B)=Sof(C9B)=Sof(H9BA)=Sof(H9BB)=Sof(H9BC)=1-FVAR(2)
 Sof(H6AA)=Sof(H6AB)=Sof(H4AA)=Sof(H4AB)=Sof(C9A)=Sof(H9AA)=Sof(H9AB)=
 Sof(H9AC)=Sof(C7A)=Sof(H7AA)=Sof(H7AB)=Sof(C3A)=Sof(H3A)=FVAR(2)
 Sof(B1B)=Sof(H1BA)=Sof(H1BB)=Sof(Cl1B)=1-FVAR(3)
 Sof(Cl1A)=Sof(B1A)=Sof(H1AA)=Sof(H1AB)=FVAR(3)
5.a Ternary CH refined with riding coordinates:
 C17(H17), C38(H38), C41(H41), C20(H20), C013(H013), C7B(H7B), C3A(H3A)
5.b Secondary CH2 refined with riding coordinates:
 B2A(H2AA,H2AB), B2B(H2BA,H2BB), C28(H28A,H28B), C3B(H3BA,H3BB), C26(H26A,
 H26B), C6(H6BC,H6BD), C6(H6AA,H6AB), C29(H29A,H29B), C4(H4BC,H4BD), C4(H4AA,
 H4AB), B1B(H1BA,H1BB), B1A(H1AA,H1AB), C7A(H7AA,H7AB)
5.c Aromatic/amide H refined with riding coordinates:
 C35(H35), C37(H37), C36(H36), C13(H13), C14(H14), C15(H15)
5.d Idealised Me refined as rotating group:
 C32(H32A,H32B,H32C), C43(H43A,H43B,H43C), C18(H18A,H18B,H18C), C39(H39A,H39B,
 H39C), C42(H42A,H42B,H42C), C19(H19A,H19B,H19C), C8(H8A,H8B,H8C), C22(H22A,
 H22B,H22C), C10(H10A,H10B,H10C), C40(H40A,H40B,H40C), C31(H31A,H31B,H31C),
 C30(H30A,H30B,H30C), C21(H21A,H21B,H21C), C9A(H9AA,H9AB,H9AC), C9B(H9BA,H9BB,
 H9BC)
;
_olex2_submission_special_instructions 'No special instructions were received'