Bis[cyclic (alkyl)(amino)carbene] isomers: Stable trans-bis(CAAC) versus facile olefin formation for cis-bis(CAAC)
Puerta Lombardi, Braulio M.; Pezoulas, Ethan R.; Suvinen, Roope A.; Harrison, Alexander; Dubrawski, Zachary S.; Gelfand, Benjamin S.; Tuononen, Heikki M.; Roesler, Roland; Chemical Communications  (2022) –; doi:10.1039/D2CC01476A

data_7130119
_publ_section_title
;
 Bis[cyclic (alkyl)(amino)carbene] isomers: Stable trans-bis(CAAC) versus
 facile olefin formation for cis-bis(CAAC)
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D2CC01476A
_journal_year                    2022
_chemical_formula_moiety         'B F4, C40 H58 N2'
_chemical_formula_sum            'C40 H58 B F4 N2'
_chemical_formula_weight         653.69
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-07-22
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272)
;
_audit_update_record
;
2021-12-27 deposited with the CCDC.	2022-04-27 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 100.0210(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.1982(2)
_cell_length_b                   22.5087(5)
_cell_length_c                   17.5373(4)
_cell_measurement_reflns_used    9808
_cell_measurement_temperature    173.15
_cell_measurement_theta_max      68.32
_cell_measurement_theta_min      4.69
_cell_volume                     3964.24(15)
_computing_cell_refinement       'SAINT V8.40A (Bruker, 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      173.15
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0479
_diffrn_reflns_av_unetI/netI     0.0319
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            52065
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.422
_diffrn_reflns_theta_min         3.225
_diffrn_source_current           0.64
_diffrn_source_power             0.0285952
_diffrn_source_voltage           44.68
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.607
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.5719
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1236 before and 0.0611 after correction.
The Ratio of minimum to maximum transmission is 0.7594.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear dark violet'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    violet
_exptl_crystal_density_diffrn    1.095
_exptl_crystal_description       plank
_exptl_crystal_F_000             1412
_exptl_crystal_size_max          0.487
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.256
_refine_diff_density_max         0.840
_refine_diff_density_min         -0.626
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     436
_refine_ls_number_reflns         7268
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0743
_refine_ls_R_factor_gt           0.0661
_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^)+(0.0912P)^2^+2.8612P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1803
_refine_ls_wR_factor_ref         0.1887
_reflns_Friedel_coverage         0.000
_reflns_number_gt                6168
_reflns_number_total             7268
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2cc01476a2.cif
_cod_data_source_block           cu_20210701_dimertritylbf4_0m_sq
_cod_database_code               7130119
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.860
_shelx_estimated_absorpt_t_min   0.757
_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
2.a Ternary CH refined with riding coordinates:
 C32(H32), C23(H23), C20(H20), C35(H35)
2.b Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B), C40(H40A,H40B), C37(H37A,H37B), C38(H38A,H38B), C39(H39A,H39B),
 C3(H3A,H3B)
2.c Aromatic/amide H refined with riding coordinates:
 C27(H27), C29(H29), C28(H28), C17(H17), C16(H16), C15(H15)
2.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C11(H11A,H11B,H11C), C31(H31A,H31B,H31C), C33(H33A,H33B,
 H33C), C6(H6A,H6B,H6C), C5(H5A,H5B,H5C), C34(H34A,H34B,H34C), C19(H19A,H19B,
 H19C), C21(H21A,H21B,H21C), C22(H22A,H22B,H22C), C36(H36A,H36B,H36C), C24(H24A,
 H24B,H24C)
;
_shelx_res_checksum              72531
_shelx_fab_checksum              8795
_olex2_submission_special_instructions 'No special instructions were received'