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_4131805
_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_formula_moiety         'C64 H90 N2'
_chemical_formula_sum            'C64 H90 N2'
_chemical_formula_weight         887.37
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2017-08-11
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5375)
;
_cell_angle_alpha                94.187(8)
_cell_angle_beta                 93.093(8)
_cell_angle_gamma                95.429(8)
_cell_formula_units_Z            1
_cell_length_a                   9.242(3)
_cell_length_b                   9.965(4)
_cell_length_c                   15.328(6)
_cell_measurement_reflns_used    6750
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      43.78
_cell_measurement_theta_min      2.90
_cell_volume                     1398.9(9)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX2 v2013.6-2 (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_detector                 'Bruker APEX-II CCD'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD Area Detector'
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.983
_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  0.0333
_diffrn_reflns_av_unetI/netI     0.0373
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            8606
_diffrn_reflns_point_group_measured_fraction_full 0.933
_diffrn_reflns_point_group_measured_fraction_max 0.933
_diffrn_reflns_theta_full        43.869
_diffrn_reflns_theta_max         43.869
_diffrn_reflns_theta_min         2.896
_diffrn_source                   'Micro Focus Rotating Anode'
_diffrn_source_type              'Bruker TXS'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.440
_exptl_absorpt_correction_T_max  0.5036
_exptl_absorpt_correction_T_min  0.4294
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0661 before and 0.0497 after correction.
The Ratio of minimum to maximum transmission is 0.8527.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            violet
_exptl_crystal_colour_primary    violet
_exptl_crystal_density_diffrn    1.053
_exptl_crystal_description       plate
_exptl_crystal_F_000             488
_exptl_crystal_size_max          0.32
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.133
_refine_diff_density_min         -0.132
_refine_diff_density_rms         0.028
_refine_ls_abs_structure_details
;
 Flack x determined using 1650 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.3(5)
_refine_ls_extinction_coef       0.0040(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     666
_refine_ls_number_reflns         3976
_refine_ls_number_restraints     164
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0421
_refine_ls_R_factor_gt           0.0395
_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^)+(0.0605P)^2^+0.2781P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1013
_refine_ls_wR_factor_ref         0.1035
_reflns_Friedel_coverage         0.899
_reflns_Friedel_fraction_full    0.884
_reflns_Friedel_fraction_max     0.884
_reflns_number_gt                3746
_reflns_number_total             3976
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            5aMenth_270K.cif
_cod_data_source_block           gb_mm140_270k_bnew
_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        1399.0(9)
_cod_database_code               4131805
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.957
_shelx_estimated_absorpt_t_min   0.872
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  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. Uiso/Uaniso restraints and constraints
Uanis(C29') = Uanis(C28') = Uanis(C30') = Uanis(C1')
Uanis(C4A) = Uanis(C4)
Uanis(C19) = Uanis(C19A)
Uanis(C25) = Uanis(C20A)
Uanis(C22) = Uanis(C22A)
3. Rigid body (RIGU) restrains
 C4, C19, C20, C21, C22, C23, C24, C25, C26, C27
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C4A, C19A, C20A, C21A, C22A, C23A, C24A, C25A, C26A, C27A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
4. Same fragment restrains
{C4, C19, C20, C21, C22, C23, C24, C25, C26, C27} sigma for 1-2: 0.02, 1-3: 0.04
as
{C4A, C19A, C20A, C21A, C22A, C23A, C24A, C25A, C26A, C27A}
5. Others
 Sof(H3BC)=Sof(H3BD)=Sof(C4A)=Sof(C19A)=Sof(H19E)=Sof(H19F)=Sof(C20A)=
 Sof(H20A)=Sof(C21A)=Sof(H21E)=Sof(H21F)=Sof(C22A)=Sof(H22E)=Sof(H22F)=
 Sof(C23A)=Sof(H23A)=Sof(C24A)=Sof(H24G)=Sof(H24H)=Sof(H24I)=Sof(C25A)=
 Sof(H25A)=Sof(C26A)=Sof(H26G)=Sof(H26H)=Sof(H26I)=Sof(C27A)=Sof(H27G)=
 Sof(H27H)=Sof(H27I)=1-FVAR(1)
 Sof(H3AA)=Sof(H3AB)=Sof(C4)=Sof(C19)=Sof(H19A)=Sof(H19B)=Sof(C20)=Sof(H20)=
 Sof(C21)=Sof(H21A)=Sof(H21B)=Sof(C22)=Sof(H22A)=Sof(H22B)=Sof(C23)=Sof(H23)=
 Sof(C24)=Sof(H24A)=Sof(H24B)=Sof(H24C)=Sof(C25)=Sof(H25)=Sof(C26)=Sof(H26A)=
 Sof(H26B)=Sof(H26C)=Sof(C27)=Sof(H27A)=Sof(H27B)=Sof(H27C)=FVAR(1)
6.a Ternary CH refined with riding coordinates:
 C11(H11), C14(H14), C20(H20), C23(H23), C25(H25), C11'(H11'), C14'(H14'),
 C20'(H20'), C23'(H23'), C25'(H25'), C20A(H20A), C23A(H23A), C25A(H25A)
6.b Secondary CH2 refined with riding coordinates:
 C3(H3AA,H3AB), C3(H3BC,H3BD), C19(H19A,H19B), C21(H21A,H21B), C22(H22A,H22B),
 C3'(H3'A,H3'B), C19'(H19C,H19D), C21'(H21C,H21D), C22'(H22C,H22D), C19A(H19E,
 H19F), C21A(H21E,H21F), C22A(H22E,H22F)
6.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C9(H9), C31(H31), C32(H32), C7'(H7'), C8'(H8'), C9'(H9'),
 C31'(H31'), C32'(H32')
6.d Idealised Me refined as rotating group:
 C12(H12A,H12B,H12C), C13(H13A,H13B,H13C), C15(H15A,H15B,H15C), C16(H16A,H16B,
 H16C), C17(H17A,H17B,H17C), C18(H18A,H18B,H18C), C24(H24A,H24B,H24C), C26(H26A,
 H26B,H26C), C27(H27A,H27B,H27C), C12'(H12D,H12E,H12F), C13'(H13D,H13E,H13F),
 C15'(H15D,H15E,H15F), C16'(H16D,H16E,H16F), C17'(H17D,H17E,H17F), C18'(H18D,
 H18E,H18F), C24'(H24D,H24E,H24F), C26'(H26D,H26E,H26F), C27'(H27D,H27E,H27F),
 C24A(H24G,H24H,H24I), C26A(H26G,H26H,H26I), C27A(H27G,H27H,H27I)
;
_shelx_res_checksum              38614
_shelx_hkl_checksum              30170
_olex2_submission_special_instructions 'No special instructions were received'