The serendipitous discovery of a readily available redox-bistable molecule derived from cyclic(alkyl)(amino)carbenes
Mahoney, Janell K.; Regnier, Vianney; Romero, Erik A.; Molton, Florian; Royal, Guy; Jazzar, Rodolphe; Martin, David; Bertrand, Guy; Organic Chemistry Frontiers 5 (2018) 2073–; doi:10.1039/C8QO00447A

data_1554353
_publ_section_title
;
 The serendipitous discovery of a readily available redox-bistable
 molecule derived from cyclic(alkyl)(amino)carbenes
;
_journal_issue                   13
_journal_name_full               'Organic Chemistry Frontiers'
_journal_page_first              2073
_journal_paper_doi               10.1039/C8QO00447A
_journal_volume                  5
_journal_year                    2018
_chemical_formula_moiety         'C45 H68 N2 O2, 2(B F4), C2 H3 N'
_chemical_formula_sum            'C47 H71 B2 F8 N3 O2'
_chemical_formula_weight         883.68
_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
_audit_creation_date             2018-01-30
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_audit_update_record
;
2018-01-31 deposited with the CCDC.
2018-05-21 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 111.6150(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   21.3381(5)
_cell_length_b                   10.2919(3)
_cell_length_c                   24.6126(6)
_cell_measurement_reflns_used    9314
_cell_measurement_temperature    100.0
_cell_measurement_theta_max      68.19
_cell_measurement_theta_min      2.35
_cell_volume                     5025.1(2)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX2 v2014.9-0 (Bruker, 2014)'
_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)'
_computing_structure_solution    'ShelXT (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.0
_diffrn_detector                 'Bruker APEX-II CCD'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD Area Detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'Kappa Four-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker APEX II Ultra'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  'Double Bounce Multilayer Mirrors'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0548
_diffrn_reflns_av_unetI/netI     0.0328
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            58527
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         68.466
_diffrn_reflns_theta_min         2.349
_diffrn_source                   'Micro Focus Rotating Anode'
_diffrn_source_type              'Bruker FR-591'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.753
_exptl_absorpt_correction_T_max  0.7531
_exptl_absorpt_correction_T_min  0.6604
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0717 before and 0.0624 after correction. The Ratio of minimum to maximum transmission is 0.8769. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.168
_exptl_crystal_description       needle
_exptl_crystal_F_000             1888
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.538
_refine_diff_density_min         -0.409
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     615
_refine_ls_number_reflns         9239
_refine_ls_number_restraints     60
_refine_ls_restrained_S_all      1.030
_refine_ls_R_factor_all          0.0641
_refine_ls_R_factor_gt           0.0515
_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^)+(0.0690P)^2^+3.6777P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1361
_refine_ls_wR_factor_ref         0.1447
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7538
_reflns_number_total             9239
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c8qo00447a2.cif
_cod_data_source_block           gb_jkm20b_0m_a_sq
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_diffrn_radiation_probe' value 'X-ray' was changed to
'x-ray' in accordance with the
/home/saulius/struct/COD-crude-data/automatic-downloads/DataCite-retrospective/RSC/depositions/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_database_code               1554353
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.963
_shelx_estimated_absorpt_t_min   0.908
_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. Rigid body (RIGU) restrains
 F5, B2, F7, F6, F8
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 F5A, B2, F7A, F8A, F6A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
3. Others
 Sof(F6A)=Sof(F5A)=Sof(F8A)=Sof(F7A)=1-FVAR(1)
 Sof(F5)=Sof(F8)=Sof(F6)=Sof(F7)=FVAR(1)
4.a Ternary CH refined with riding coordinates:
 C21(H21), C24(H24), C43(H43), C40(H40)
4.b Secondary CH2 refined with riding coordinates:
 C28(H28A,H28B), C9(H9A,H9B)
4.c Aromatic/amide H refined with riding coordinates:
 C19(H19), C17(H17), C18(H18), C36(H36), C38(H38), C37(H37)
4.d Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C7(H7A,H7B,H7C), C23(H23A,H23B,H23C), C22(H22A,H22B,H22C),
 C26(H26A,H26B,H26C), C25(H25A,H25B,H25C), C44(H44A,H44B,H44C), C14(H14A,H14B,
 H14C), C33(H33A,H33B,H33C), C12(H12A,H12B,H12C), C41(H41A,H41B,H41C), C11(H11A,
 H11B,H11C), C30(H30A,H30B,H30C), C45(H45A,H45B,H45C), C13(H13A,H13B,H13C),
 C42(H42A,H42B,H42C), C32(H32A,H32B,H32C), C31(H31A,H31B,H31C), C50A(H50A,H50B,
 H50C)
;
_shelx_res_checksum              25275
_shelx_hkl_checksum              99496
_shelx_fab_checksum              48399
_olex2_submission_special_instructions 'No special instructions were received'