Modular Approach to Kekulé Diradicaloids Derived from Cyclic (Alkyl)(amino)carbenes.
Hansmann, Max M.; Melaimi, Mohand; Munz, Dominik; Bertrand, Guy; Journal of the American Chemical Society 140 (2018) 2546–2554; doi:10.1021/jacs.7b11183

data_4131801
_publ_section_title
;
 Modular Approach to Kekul\'e Diradicaloids Derived from Cyclic
 (Alkyl)(amino)carbenes.
;
_journal_issue                   7
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              2546
_journal_page_last               2554
_journal_paper_doi               10.1021/jacs.7b11183
_journal_volume                  140
_journal_year                    2018
_chemical_absolute_configuration ad
_chemical_formula_moiety         'F6 Sb, C64 H90 N2, C4 H8 O'
_chemical_formula_sum            'C68 H98 F6 N2 O Sb'
_chemical_formula_weight         1195.23
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
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_audit_creation_method
;
Olex2 1.2-beta
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5375)
;
_cell_angle_alpha                98.484(7)
_cell_angle_beta                 93.383(7)
_cell_angle_gamma                96.918(7)
_cell_formula_units_Z            1
_cell_length_a                   9.311(2)
_cell_length_b                   13.035(3)
_cell_length_c                   14.124(3)
_cell_measurement_reflns_used    9484
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.37
_cell_measurement_theta_min      2.21
_cell_volume                     1678.0(6)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX2 v2014.11-0 (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, 2015)'
_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 0.995
_diffrn_measurement_device       'Kappa Four-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker X8 APEX II'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0207
_diffrn_reflns_av_unetI/netI     0.0321
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            26157
_diffrn_reflns_point_group_measured_fraction_full 0.894
_diffrn_reflns_point_group_measured_fraction_max 0.887
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.377
_diffrn_reflns_theta_min         1.987
_diffrn_source                   'sealed tube'
_diffrn_source_type              fine-focus
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.467
_exptl_absorpt_correction_T_max  0.2627
_exptl_absorpt_correction_T_min  0.2351
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0607 before and 0.0432 after correction. The Ratio of minimum to maximum transmission is 0.8949. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            pink
_exptl_crystal_density_diffrn    1.183
_exptl_crystal_description       block
_exptl_crystal_F_000             633
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.29
_refine_diff_density_max         0.468
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.048
_refine_ls_abs_structure_details
;
 Flack x determined using 4418 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.012(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     721
_refine_ls_number_reflns         10936
_refine_ls_number_restraints     33
_refine_ls_restrained_S_all      1.049
_refine_ls_R_factor_all          0.0292
_refine_ls_R_factor_gt           0.0283
_refine_ls_shift/su_max          0.014
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0334P)^2^+0.6009P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0681
_refine_ls_wR_factor_ref         0.0687
_reflns_Friedel_coverage         0.783
_reflns_Friedel_fraction_full    0.788
_reflns_Friedel_fraction_max     0.779
_reflns_number_gt                10700
_reflns_number_total             10936
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            5cMenth_100K.cif
_cod_data_source_block           gb_mm136_0m_b_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/ACS/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_original_cell_volume        1677.9(6)
_cod_database_code               4131801
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.876
_shelx_estimated_absorpt_t_min   0.861
_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
 C3, C4, C1, C23, C19
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.004
 Sb01
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.004
3.a Ternary CH refined with riding coordinates:
 C11B(H11B), C14B(H14B), C11(H11), C20B(H20B), C25(H25), C23B(H23B), C20(H20),
 C23(H23), C25B(H25B), C14(H14)
3.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C22B(H22A,H22B), C21B(H21A,H21B), C19B(H19A,H19B), C19(H19C,
 H19D), C3B(H3BA,H3BB), C21(H21C,H21D), C22(H22C,H22D), C36(H36A,H36B),
 C35(H35A,H35B), C34(H34A,H34B), C33(H33A,H33B)
3.c Aromatic/amide H refined with riding coordinates:
 C9(H9), C8B(H8B), C32B(H32B), C7(H7), C31(H31), C31B(H31B), C9B(H9B),
 C32(H32), C8(H8), C7B(H7B)
3.d Idealised Me refined as rotating group:
 C15B(H15A,H15B,H15C), C17B(H17A,H17B,H17C), C17(H17D,H17E,H17F), C13(H13A,
 H13B,H13C), C12B(H12A,H12B,H12C), C18B(H18A,H18B,H18C), C16B(H16A,H16B,H16C),
 C16(H16D,H16E,H16F), C24B(H24A,H24B,H24C), C18(H18D,H18E,H18F), C15(H15D,H15E,
 H15F), C27B(H27A,H27B,H27C), C12(H12D,H12E,H12F), C26(H26A,H26B,H26C),
 C13B(H13D,H13E,H13F), C26B(H26D,H26E,H26F), C27(H27D,H27E,H27F), C24(H24D,H24E,
 H24F)
;
_shelx_res_checksum              42034
_shelx_hkl_checksum              31882
_shelx_fab_checksum              78865
_olex2_submission_special_instructions 'No special instructions were received'