A Crystalline Monomeric Allenyl/Propargyl Radical.
Hansmann, Max M.; Melaimi, Mohand; Bertrand, Guy; Journal of the American Chemical Society  (2017) –; doi:10.1021/jacs.7b09622

data_4126643
_publ_section_title
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 A Crystalline Monomeric Allenyl/Propargyl Radical.
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_paper_doi               10.1021/jacs.7b09622
_journal_year                    2017
_chemical_formula_moiety         'F6 Sb, C43 H50 N'
_chemical_formula_sum            'C43 H50 F6 N Sb'
_chemical_formula_weight         816.59
_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'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2017-09-02
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                90
_cell_angle_beta                 94.923(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   13.4623(5)
_cell_length_b                   23.1356(7)
_cell_length_c                   14.0612(5)
_cell_measurement_reflns_used    6076
_cell_measurement_temperature    100
_cell_measurement_theta_max      22.181
_cell_measurement_theta_min      2.325
_cell_volume                     4363.3(3)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'APEX2 v2014.11-0 (Bruker, 2014)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_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 0.999
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device       'Kappa Four-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w 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  0.0760
_diffrn_reflns_av_unetI/netI     0.1008
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            27487
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.357
_diffrn_reflns_theta_min         1.699
_diffrn_source                   'sealed tube'
_diffrn_source_type              fine-focus
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.685
_exptl_absorpt_correction_T_max  0.4868
_exptl_absorpt_correction_T_min  0.4352
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0761 before and 0.0694 after correction. The Ratio of minimum to maximum transmission is 0.9035. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.243
_exptl_crystal_description       block
_exptl_crystal_F_000             1680
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.2
_refine_diff_density_max         1.017
_refine_diff_density_min         -1.937
_refine_diff_density_rms         0.103
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.168
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     544
_refine_ls_number_reflns         7947
_refine_ls_number_restraints     304
_refine_ls_restrained_S_all      1.149
_refine_ls_R_factor_all          0.1268
_refine_ls_R_factor_gt           0.0914
_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^)+29.6290P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1839
_refine_ls_wR_factor_ref         0.1962
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5565
_reflns_number_total             7947
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            3d.cif
_cod_data_source_block           gb_mm148_0m_a_sq
_cod_depositor_comments
;
The following automatic conversions were performed:

'_diffrn_radiation_probe' value 'X-ray' changed to 'x-ray' according
to
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 4973 2017-02-22 13:04:09Z antanas 
;
_cod_database_code               4126643
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.875
_shelx_estimated_absorpt_t_min   0.847
_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. Restrained distances
 C25'-C24 \\sim C25-C24
 with sigma of 0.01
 C26-C25 \\sim C26'-C25' \\sim C32-C25 \\sim C32'-C25' \\sim C38'-C25' \\sim
C38-C25
 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
Uanis(C37) = Uanis(C37')
Uanis(C36) = Uanis(C36')
Uanis(C35') = Uanis(C35)
Uanis(C34') = Uanis(C34)
Uanis(C33') = Uanis(C33)
Uanis(C32) = Uanis(C32')
Uanis(C39') = Uanis(C39)
Uanis(C40') = Uanis(C40)
Uanis(C41) = Uanis(C41')
Uanis(C42) = Uanis(C42')
Uanis(C43') = Uanis(C43)
Uanis(C26) = Uanis(C26')
Uanis(C27') = Uanis(C27)
Uanis(C28) = Uanis(C28')
Uanis(C29) = Uanis(C29')
Uanis(C30) = Uanis(C30')
Uanis(C31) = Uanis(C31')
Uanis(C19') = Uanis(C20)
Uanis(C21) = Uanis(C22')
Uanis(C4) = Uanis(C4')
Uanis(C38') = Uanis(C38)
Uanis(C25') = Uanis(C25)
4. Rigid body (RIGU) restrains
 C32, C37, C33, C36, C34, C35
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.004
 C32', C34', C37', C35', C36', C33'
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.004
 C38, C43, C39, C42, C40, C41
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.004
 C41', C40', C38', C43', C42', C39'
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.004
 C26, C27, C31, C28, C30, C29
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.004
 C26', C31', C28', C27', C30', C29'
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.004
 C4', C19', C20, C4, C19, C21', C21, C22, C22', C20'
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.004
 C18, C17, C2, C3, C4, C1
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.004
5. Others
 Sof(H3BC)=Sof(H3BD)=Sof(C4')=Sof(C21')=Sof(H21A)=Sof(H21B)=Sof(C22')=
 Sof(H22A)=Sof(H22B)=Sof(H22C)=Sof(C20')=Sof(H20D)=Sof(H20E)=Sof(H20F)=
 Sof(C19')=Sof(H19C)=Sof(H19D)=1-FVAR(1)
 Sof(H3A)=Sof(H3B)=Sof(C4)=Sof(C19)=Sof(H19A)=Sof(H19B)=Sof(C20)=Sof(H20A)=
 Sof(H20B)=Sof(H20C)=Sof(C22)=Sof(H22D)=Sof(H22E)=Sof(H22F)=Sof(C21)=Sof(H21C)=
 Sof(H21D)=FVAR(1)
 Sof(C32')=Sof(C34')=Sof(H34')=Sof(C37')=Sof(H37')=Sof(C35')=Sof(H35')=
 Sof(C36')=Sof(H36')=Sof(C33')=Sof(H33')=Sof(C41')=Sof(H41')=Sof(C40')=
 Sof(H40')=Sof(C38')=Sof(C43')=Sof(H43')=Sof(C42')=Sof(H42')=Sof(C39')=
 Sof(H39')=Sof(C26')=Sof(C31')=Sof(H31')=Sof(C28')=Sof(H28')=Sof(C27')=
 Sof(H27')=Sof(C30')=Sof(H30')=Sof(C29')=Sof(H29')=Sof(C25')=1-FVAR(2)
 Sof(C25)=Sof(C38)=Sof(C43)=Sof(H43)=Sof(C42)=Sof(H42)=Sof(C41)=Sof(H41)=
 Sof(C40)=Sof(H40)=Sof(C39)=Sof(H39)=Sof(C26)=Sof(C27)=Sof(H27)=Sof(C31)=
 Sof(H31)=Sof(C28)=Sof(H28)=Sof(C30)=Sof(H30)=Sof(C29)=Sof(H29)=Sof(C32)=
 Sof(C37)=Sof(H37)=Sof(C36)=Sof(H36)=Sof(C34)=Sof(H34)=Sof(C33)=Sof(H33)=
 Sof(C35)=Sof(H35)=FVAR(2)
6.a Ternary CH refined with riding coordinates:
 C11(H11), C14(H14)
6.b Secondary CH2 refined with riding coordinates:
 C3(H3BC,H3BD), C3(H3A,H3B), C19(H19A,H19B), C21'(H21A,H21B), C19'(H19C,H19D),
 C21(H21C,H21D)
6.c Aromatic/amide H refined with riding coordinates:
 C7(H7), C8(H8), C43(H43), C42(H42), C41(H41), C40(H40), C39(H39), C9(H9),
 C27(H27), C31(H31), C28(H28), C30(H30), C29(H29), C34'(H34'), C37'(H37'),
 C35'(H35'), C36'(H36'), C33'(H33'), C37(H37), C36(H36), C34(H34), C33(H33),
 C41'(H41'), C40'(H40'), C43'(H43'), C42'(H42'), C39'(H39'), C35(H35),
 C31'(H31'), C28'(H28'), C27'(H27'), C30'(H30'), C29'(H29')
6.d Fitted hexagon refined as free rotating group:
 C38(C43,C42,C41,C40,C39)
6.e Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C12(H12A,H12B,H12C), C17(H17A,H17B,H17C), C15(H15A,H15B,
 H15C), C18(H18A,H18B,H18C), C16(H16A,H16B,H16C), C20(H20A,H20B,H20C),
 C22'(H22A,H22B,H22C), C20'(H20D,H20E,H20F), C22(H22D,H22E,H22F)
;
_shelx_res_checksum              316
_shelx_hkl_checksum              85217
_shelx_fab_checksum              72737
_olex2_submission_special_instructions 'No special instructions were received'