Cyclic (Alkyl)(amino)carbene Ligand-Promoted Nitro Deoxygenative Hydroboration with Chromium Catalysis: Scope, Mechanism, and Applications.
Zhao, Lixing; Hu, Chenyang; Cong, Xuefeng; Deng, Gongda; Liu, Liu Leo; Luo, Meiming; Zeng, Xiaoming; Journal of the American Chemical Society 143 (2021) 1618–1629; doi:10.1021/jacs.0c12318

data_4135611
_publ_section_title
;
 Cyclic (Alkyl)(amino)carbene Ligand-Promoted Nitro Deoxygenative
 Hydroboration with Chromium Catalysis: Scope, Mechanism, and
 Applications.
;
_journal_issue                   3
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              1618
_journal_page_last               1629
_journal_paper_doi               10.1021/jacs.0c12318
_journal_volume                  143
_journal_year                    2021
_chemical_formula_moiety         'C36 H56 Cl3 Cr N2 O'
_chemical_formula_sum            'C36 H56 Cl3 Cr N2 O'
_chemical_formula_weight         691.17
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2020-06-24
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 94.665(4)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   29.890(4)
_cell_length_b                   18.583(4)
_cell_length_c                   18.248(3)
_cell_measurement_reflns_used    6206
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      23.36
_cell_measurement_theta_min      2.24
_cell_volume                     10102(3)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      296.15
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0354
_diffrn_reflns_av_unetI/netI     0.0414
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       35
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            25001
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.098
_diffrn_reflns_theta_max         25.098
_diffrn_reflns_theta_min         2.192
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.407
_exptl_absorpt_correction_T_max  0.7453
_exptl_absorpt_correction_T_min  0.6780
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0636 before and 0.0368 after correction.
The Ratio of minimum to maximum transmission is 0.9097.
The \l/2 correction factor is 0.0015.
;
_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    0.909
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             2952
_exptl_crystal_size_max          0.356
_exptl_crystal_size_mid          0.276
_exptl_crystal_size_min          0.143
_refine_diff_density_max         0.364
_refine_diff_density_min         -0.324
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     389
_refine_ls_number_reflns         8941
_refine_ls_number_restraints     45
_refine_ls_restrained_S_all      1.180
_refine_ls_R_factor_all          0.0601
_refine_ls_R_factor_gt           0.0443
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0792P)^2^+0.7213P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1281
_refine_ls_wR_factor_ref         0.1385
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6637
_reflns_number_total             8941
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja0c12318_si_002.cif
_cod_data_source_block           xb0545_sq
_cod_database_code               4135611
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.944
_shelx_estimated_absorpt_t_min   0.869
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2. Rigid bond restraints
 C18, C19
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C2, N23
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
3. Uiso/Uaniso restraints and constraints
C18 \\sim C19: within 2A with sigma of 0.001 and sigma for terminal atoms of
0.02
C2 \\sim N23: within 2A with sigma of 0.001 and sigma for terminal atoms of 0.02
N23 \\sim C51: within 2A with sigma of 0.001 and sigma for terminal atoms of
0.02
C18 \\sim C2: within 2A with sigma of 0.001 and sigma for terminal atoms of
0.001
C13 \\sim C18: within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02
4.a Rotating group:
 O1(H1A,H1B)
4.b Ternary CH refined with riding coordinates:
 C3(H3), C10(H10), C30(H30), C33(H33)
4.c Secondary CH2 refined with riding coordinates:
 C24(H24A,H24B)
4.d Me refined with riding coordinates:
 C1(H1C,H1D,H1E), C0AA(H0AA,H0AB,H0AC), C11(H11A,H11B,H11C), C12(H12A,H12B,
 H12C), C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C17(H17A,H17B,H17C), C19(H19A,
 H19B,H19C), C21(H21A,H21B,H21C), C22(H22A,H22B,H22C), C31(H31A,H31B,H31C),
 C32(H32A,H32B,H32C), C34(H34A,H34B,H34C), C35(H35A,H35B,H35C)
4.e Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C26(H26), C27(H27), C28(H28)
;
_shelx_res_checksum              61343
_shelx_hkl_checksum              22752
_shelx_fab_checksum              57282
_olex2_submission_special_instructions 'No special instructions were received'