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_4126642
_publ_section_title
;
 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         '1(C70 H96 N2)'
_chemical_formula_sum            'C70 H96 N2'
_chemical_formula_weight         965.48
_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_Hall           'P 1'
_space_group_name_H-M_alt        'P 1'
_symmetry_space_group_name_Hall  'P 1'
_symmetry_space_group_name_H-M   '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                78.446(3)
_cell_angle_beta                 84.586(3)
_cell_angle_gamma                88.562(3)
_cell_formula_units_Z            2
_cell_length_a                   12.5961(12)
_cell_length_b                   15.6929(16)
_cell_length_c                   16.3566(17)
_cell_measurement_reflns_used    9927
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      20.41
_cell_measurement_theta_min      2.22
_cell_volume                     3153.5(5)
_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 1.000
_diffrn_measured_fraction_theta_max 1.000
_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           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0419
_diffrn_reflns_av_unetI/netI     0.0421
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            49730
_diffrn_reflns_point_group_measured_fraction_full 0.902
_diffrn_reflns_point_group_measured_fraction_max 0.902
_diffrn_reflns_theta_full        21.725
_diffrn_reflns_theta_max         21.725
_diffrn_reflns_theta_min         1.276
_diffrn_source                   'Micro Focus Rotating Anode'
_diffrn_source_type              'Bruker TXS'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.057
_exptl_absorpt_correction_T_max  0.4889
_exptl_absorpt_correction_T_min  0.4653
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0554 before and 0.0465 after correction. The Ratio of minimum to maximum transmission is 0.9517. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.017
_exptl_crystal_description       block
_exptl_crystal_F_000             1060
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.581
_refine_diff_density_min         -0.238
_refine_diff_density_rms         0.065
_refine_ls_abs_structure_details
;
 Flack x determined using 3462 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.5(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.299
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1777
_refine_ls_number_reflns         13473
_refine_ls_number_restraints     2031
_refine_ls_restrained_S_all      1.307
_refine_ls_R_factor_all          0.1402
_refine_ls_R_factor_gt           0.1063
_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2914
_refine_ls_wR_factor_ref         0.3244
_reflns_Friedel_coverage         0.803
_reflns_Friedel_fraction_full    0.803
_reflns_Friedel_fraction_max     0.803
_reflns_number_gt                9542
_reflns_number_total             13473
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            7b.cif
_cod_data_source_block           reint1_b_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               4126642
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.989
_shelx_estimated_absorpt_t_min   0.989
_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. Restrained distances
 C15E-C14E
 1.52 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
Uanis(C1D) = Uanis(C8CA)
Uanis(C8D) = Uanis(C21E)
Uanis(C14D) = Uanis(C24E)
Uanis(C6D) = Uanis(C22E)
Uanis(C15D) = Uanis(C26E)
Uanis(C16D) = Uanis(C25E)
Uanis(C5D) = Uanis(C4E)
Uanis(C2D) = Uanis(C2E)
Uanis(C28A) = Uanis(C28F)
Uanis(C1A) = Uanis(C1F)
Uanis(C11A) = Uanis(C22F)
Uanis(C5A) = Uanis(C4F)
Uanis(C22A) = Uanis(C14F)
Uanis(C14A) = Uanis(C24F)
Uanis(C15A) = Uanis(C25F)
Uanis(C19D) = Uanis(C5E)
4. Rigid body (RIGU) restrains
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Same fragment restrains
{N1A, C1A, C2A, C3A, C4A, C5A, C6A, C7A, C8A, C9A, C10A, C11A, C12A, C13A,
C14A, C15A, C16A, C17A, C18A, C19A, C20A, C21A, C22A, C23A, C24A, C25A, C26A,
C27A, C28A} sigma for 1-2: 0.02, 1-3: 0.04
as
{N1B, C1B, C2B, C3B, C4B, C5B, C6B, C7B, C8B, C9B, C10B, C11B, C12B, C13B,
C14B, C15B, C16B, C17B, C18B, C19B, C20B, C21B, C22B, C23B, C24B, C25B, C26B,
C27B, C28B}
{N1D, C1D, C2D, C3D, C4D, C5D, C6D, C7D, C8D, C9D, C10D, C11D, C12D, C13D,
C14D, C15D, C16D, C17D, C18D, C19D, C20D, C21D, C22D, C23D, C24D, C25D, C26D,
C27D, C28D} sigma for 1-2: 0.02, 1-3: 0.04
as
{N1E, C8CA, C2E, C3E, C4E, C5E, C6E, C7E, C8E, C9E, C10E, C11E, C12E, C13E,
C14E, C15E, C16E, C17E, C18E, C19E, C20E, C21E, C22E, C23E, C24E, C25E, C26E,
C27E, C28E}
{N1A, C1A, C2A, C3A, C4A, C5A, C6A, C7A, C8A, C9A, C10A, C11A, C12A, C13A,
C14A, C15A, C16A, C17A, C18A, C19A, C20A, C21A, C22A, C23A, C24A, C25A, C26A,
C27A, C28A} sigma for 1-2: 0.02, 1-3: 0.04
as
{N1F, C1F, C2F, C3F, C4F, C5F, C6F, C7F, C8F, C9F, C10F, C11F, C12F, C13F,
C14F, C15F, C16F, C17F, C18F, C19F, C20F, C21F, C22F, C23F, C24F, C25F, C26F,
C27F, C28F}
6. Others
 Sof(N1E)=Sof(C8CA)=Sof(C2E)=Sof(C3E)=Sof(H3EA)=Sof(H3EB)=Sof(C4E)=Sof(C5E)=
 Sof(C6E)=Sof(C7E)=Sof(H7E)=Sof(C8E)=Sof(H8E)=Sof(C9E)=Sof(H9E)=Sof(C10E)=
 Sof(C11E)=Sof(H11E)=Sof(C12E)=Sof(H12P)=Sof(H12Q)=Sof(H12R)=Sof(C13E)=
 Sof(H13P)=Sof(H13Q)=Sof(H13R)=Sof(C14E)=Sof(H14E)=Sof(C15E)=Sof(H15P)=
 Sof(H15Q)=Sof(H15R)=Sof(C16E)=Sof(H16P)=Sof(H16Q)=Sof(H16R)=Sof(C17E)=
 Sof(H17P)=Sof(H17Q)=Sof(H17R)=Sof(C18E)=Sof(H18P)=Sof(H18Q)=Sof(H18R)=
 Sof(C19E)=Sof(H19E)=Sof(C20E)=Sof(H20K)=Sof(H20L)=Sof(C21E)=Sof(H21K)=
 Sof(H21L)=Sof(C22E)=Sof(H22E)=Sof(C23E)=Sof(H23K)=Sof(H23L)=Sof(C24E)=
 Sof(H24E)=Sof(C25E)=Sof(H25P)=Sof(H25Q)=Sof(H25R)=Sof(C26E)=Sof(H26P)=
 Sof(H26Q)=Sof(H26R)=Sof(C27E)=Sof(H27P)=Sof(H27Q)=Sof(H27R)=Sof(C28E)=1-FVAR(1)
 Sof(N1D)=Sof(C1D)=Sof(C2D)=Sof(C3D)=Sof(H3DA)=Sof(H3DB)=Sof(C4D)=Sof(C5D)=
 Sof(C6D)=Sof(C7D)=Sof(H7D)=Sof(C8D)=Sof(H8D)=Sof(C9D)=Sof(H9D)=Sof(C10D)=
 Sof(C11D)=Sof(H11D)=Sof(C12D)=Sof(H12M)=Sof(H12N)=Sof(H12O)=Sof(C13D)=
 Sof(H13M)=Sof(H13N)=Sof(H13O)=Sof(C14D)=Sof(H14D)=Sof(C15D)=Sof(H15M)=
 Sof(H15N)=Sof(H15O)=Sof(C16D)=Sof(H16M)=Sof(H16N)=Sof(H16O)=Sof(C17D)=
 Sof(H17M)=Sof(H17N)=Sof(H17O)=Sof(C18D)=Sof(H18M)=Sof(H18N)=Sof(H18O)=
 Sof(C19D)=Sof(H19D)=Sof(C20D)=Sof(H20I)=Sof(H20J)=Sof(C21D)=Sof(H21I)=
 Sof(H21J)=Sof(C22D)=Sof(H22D)=Sof(C23D)=Sof(H23I)=Sof(H23J)=Sof(C24D)=
 Sof(H24D)=Sof(C25D)=Sof(H25M)=Sof(H25N)=Sof(H25O)=Sof(C26D)=Sof(H26M)=
 Sof(H26N)=Sof(H26O)=Sof(C27D)=Sof(H27M)=Sof(H27N)=Sof(H27O)=Sof(C28D)=FVAR(1)
 Sof(N1F)=Sof(C1F)=Sof(C2F)=Sof(C3F)=Sof(H3FA)=Sof(H3FB)=Sof(C4F)=Sof(C5F)=
 Sof(C6F)=Sof(C7F)=Sof(H7F)=Sof(C8F)=Sof(H8F)=Sof(C9F)=Sof(H9F)=Sof(C10F)=
 Sof(C11F)=Sof(H11F)=Sof(C12F)=Sof(H12G)=Sof(H12H)=Sof(H12I)=Sof(C13F)=
 Sof(H13G)=Sof(H13H)=Sof(H13I)=Sof(C14F)=Sof(H14F)=Sof(C15F)=Sof(H15G)=
 Sof(H15H)=Sof(H15I)=Sof(C16F)=Sof(H16G)=Sof(H16H)=Sof(H16I)=Sof(C17F)=
 Sof(H17G)=Sof(H17H)=Sof(H17I)=Sof(C18F)=Sof(H18G)=Sof(H18H)=Sof(H18I)=
 Sof(C19F)=Sof(H19F)=Sof(C20F)=Sof(H20E)=Sof(H20F)=Sof(C21F)=Sof(H21E)=
 Sof(H21F)=Sof(C22F)=Sof(H22F)=Sof(C23F)=Sof(H23E)=Sof(H23F)=Sof(C24F)=
 Sof(H24F)=Sof(C25F)=Sof(H25G)=Sof(H25H)=Sof(H25I)=Sof(C26F)=Sof(H26G)=
 Sof(H26H)=Sof(H26I)=Sof(C27F)=Sof(H27G)=Sof(H27H)=Sof(H27I)=Sof(C28F)=1-FVAR(2)
 Sof(N1A)=Sof(C1A)=Sof(C2A)=Sof(C3A)=Sof(H3AA)=Sof(H3AB)=Sof(C4A)=Sof(C5A)=
 Sof(C6A)=Sof(C7A)=Sof(H7A)=Sof(C8A)=Sof(H8A)=Sof(C9A)=Sof(H9A)=Sof(C10A)=
 Sof(C11A)=Sof(H11A)=Sof(C12A)=Sof(H12A)=Sof(H12B)=Sof(H12C)=Sof(C13A)=
 Sof(H13A)=Sof(H13B)=Sof(H13C)=Sof(C14A)=Sof(H14A)=Sof(C15A)=Sof(H15A)=
 Sof(H15B)=Sof(H15C)=Sof(C16A)=Sof(H16A)=Sof(H16B)=Sof(H16C)=Sof(C17A)=
 Sof(H17A)=Sof(H17B)=Sof(H17C)=Sof(C18A)=Sof(H18A)=Sof(H18B)=Sof(H18C)=
 Sof(C19A)=Sof(H19A)=Sof(C20A)=Sof(H20A)=Sof(H20B)=Sof(C21A)=Sof(H21A)=
 Sof(H21B)=Sof(C22A)=Sof(H22A)=Sof(C23A)=Sof(H23A)=Sof(H23B)=Sof(C24A)=
 Sof(H24A)=Sof(C25A)=Sof(H25A)=Sof(H25B)=Sof(H25C)=Sof(C26A)=Sof(H26A)=
 Sof(H26B)=Sof(H26C)=Sof(C27A)=Sof(H27A)=Sof(H27B)=Sof(H27C)=Sof(C28A)=FVAR(2)
7.a Ternary CH refined with riding coordinates:
 C11A(H11A), C14A(H14A), C19A(H19A), C22A(H22A), C24A(H24A), C11B(H11B),
 C14B(H14B), C19B(H19B), C22B(H22B), C24B(H24B), C33B(H33B), C11C(H11C),
 C14C(H14C), C19C(H19C), C22C(H22C), C24C(H24C), C11D(H11D), C14D(H14D),
 C19D(H19D), C22D(H22D), C24D(H24D), C33D(H33D), C11E(H11E), C14E(H14E),
 C19E(H19E), C22E(H22E), C24E(H24E), C11F(H11F), C14F(H14F), C19F(H19F),
 C22F(H22F), C24F(H24F)
7.b Secondary CH2 refined with riding coordinates:
 C3A(H3AA,H3AB), C20A(H20A,H20B), C21A(H21A,H21B), C23A(H23A,H23B), C3B(H3BA,
 H3BB), C20B(H20C,H20D), C21B(H21C,H21D), C23B(H23C,H23D), C3C(H3CA,H3CB),
 C20C(H20G,H20H), C21C(H21G,H21H), C23C(H23G,H23H), C3D(H3DA,H3DB), C20D(H20I,
 H20J), C21D(H21I,H21J), C23D(H23I,H23J), C3E(H3EA,H3EB), C20E(H20K,H20L),
 C21E(H21K,H21L), C23E(H23K,H23L), C3F(H3FA,H3FB), C20F(H20E,H20F), C21F(H21E,
 H21F), C23F(H23E,H23F)
7.c Me refined with riding coordinates:
 C25F(H25G,H25H,H25I), C26F(H26G,H26H,H26I)
7.d Aromatic/amide H refined with riding coordinates:
 C7A(H7A), C8A(H8A), C9A(H9A), C31A(H31A), C32A(H32A), C33A(H33A), C34A(H34A),
 C35A(H35A), C7B(H7B), C8B(H8B), C9B(H9B), C31B(H31B), C32B(H32B), C34B(H34B),
 C35B(H35B), C7C(H7C), C8C(H8C), C9C(H9C), C31C(H31C), C32C(H32C), C33C(H33C),
 C34C(H34C), C35C(H35C), C7D(H7D), C8D(H8D), C9D(H9D), C31D(H31D), C32D(H32D),
 C34D(H34D), C35D(H35D), C7E(H7E), C8E(H8E), C9E(H9E), C7F(H7F), C8F(H8F),
 C9F(H9F)
7.e Idealised Me refined as rotating group:
 C12A(H12A,H12B,H12C), C13A(H13A,H13B,H13C), C15A(H15A,H15B,H15C), C16A(H16A,
 H16B,H16C), C17A(H17A,H17B,H17C), C18A(H18A,H18B,H18C), C25A(H25A,H25B,H25C),
 C26A(H26A,H26B,H26C), C27A(H27A,H27B,H27C), C12B(H12D,H12E,H12F), C13B(H13D,
 H13E,H13F), C15B(H15D,H15E,H15F), C16B(H16D,H16E,H16F), C17B(H17D,H17E,H17F),
 C18B(H18D,H18E,H18F), C25B(H25D,H25E,H25F), C26B(H26D,H26E,H26F), C27B(H27D,
 H27E,H27F), C12C(H12J,H12K,H12L), C13C(H13J,H13K,H13L), C15C(H15J,H15K,H15L),
 C16C(H16J,H16K,H16L), C17C(H17J,H17K,H17L), C18C(H18J,H18K,H18L), C25C(H25J,
 H25K,H25L), C26C(H26J,H26K,H26L), C27C(H27J,H27K,H27L), C12D(H12M,H12N,H12O),
 C13D(H13M,H13N,H13O), C15D(H15M,H15N,H15O), C16D(H16M,H16N,H16O), C17D(H17M,
 H17N,H17O), C18D(H18M,H18N,H18O), C25D(H25M,H25N,H25O), C26D(H26M,H26N,H26O),
 C27D(H27M,H27N,H27O), C12E(H12P,H12Q,H12R), C13E(H13P,H13Q,H13R), C15E(H15P,
 H15Q,H15R), C16E(H16P,H16Q,H16R), C17E(H17P,H17Q,H17R), C18E(H18P,H18Q,H18R),
 C25E(H25P,H25Q,H25R), C26E(H26P,H26Q,H26R), C27E(H27P,H27Q,H27R), C12F(H12G,
 H12H,H12I), C13F(H13G,H13H,H13I), C15F(H15G,H15H,H15I), C16F(H16G,H16H,H16I),
 C17F(H17G,H17H,H17I), C18F(H18G,H18H,H18I), C27F(H27G,H27H,H27I)
;
_shelx_res_checksum              47896
_shelx_hkl_checksum              13846
_shelx_fab_checksum              5189
_olex2_submission_special_instructions 'No special instructions were received'