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_4126646
_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         'C60 H80 N2'
_chemical_formula_sum            'C60 H80 N2'
_chemical_formula_weight         829.26
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_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             2017-08-07
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2017.07.20 svn.r3457 for OlexSys, GUI svn.r5370)
;
_cell_angle_alpha                78.37(2)
_cell_angle_beta                 81.016(19)
_cell_angle_gamma                75.52(2)
_cell_formula_units_Z            2
_cell_length_a                   11.340(3)
_cell_length_b                   12.577(4)
_cell_length_c                   18.802(5)
_cell_measurement_reflns_used    9994
_cell_measurement_temperature    100
_cell_measurement_theta_max      68.260
_cell_measurement_theta_min      3.717
_cell_volume                     2527.3(13)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2017)'
_computing_data_collection       'APEX3 v2016.1-0 (Bruker, 2016)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2017)'
_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 Platinum135 CCD'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CCD Area Detector'
_diffrn_measured_fraction_theta_full 0.978
_diffrn_measured_fraction_theta_max 0.958
_diffrn_measurement_device       'Fixed Chi Three-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Platinum135'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  'Multilayer Mirrors'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_reflns_av_R_equivalents  0.0386
_diffrn_reflns_av_unetI/netI     0.0483
_diffrn_reflns_Laue_measured_fraction_full 0.978
_diffrn_reflns_Laue_measured_fraction_max 0.958
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            15019
_diffrn_reflns_point_group_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.958
_diffrn_reflns_theta_full        67.500
_diffrn_reflns_theta_max         68.958
_diffrn_reflns_theta_min         2.414
_diffrn_source                   'Micro Focus Rotating Anode'
_diffrn_source_type              'Bruker FR-591'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.458
_exptl_absorpt_correction_T_max  0.521
_exptl_absorpt_correction_T_min  0.407
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 TWINABS-2012/1 (Bruker,2012) was used for absorption correction.
 
For component 1:
 wR2(int) was 0.0650 before and 0.0559 after correction.
 The Ratio of minimum to maximum transmission is 0.78.
 The \l/2 correction factor is Not present
 
For component 2:
 wR2(int) was 0.0883 before and 0.0666 after correction.
 The Ratio of minimum to maximum transmission is 0.78.
 The \l/2 correction factor is Not present

Final HKLF 4 output contains 78784 reflections, Rint = 0.0562
 (42570 with I > 3sig(I), Rint = 0.0478)
;
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.090
_exptl_crystal_description       plate
_exptl_crystal_F_000             908
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.115
_refine_diff_density_max         0.400
_refine_diff_density_min         -0.300
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.183
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     857
_refine_ls_number_reflns         8997
_refine_ls_number_restraints     474
_refine_ls_restrained_S_all      1.164
_refine_ls_R_factor_all          0.0793
_refine_ls_R_factor_gt           0.0687
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+3.1480P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1543
_refine_ls_wR_factor_ref         0.1583
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7760
_reflns_number_total             8997
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            5a.cif
_cod_data_source_block           mm104
_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_original_cell_volume        2527.2(12)
_cod_database_code               4126646
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.949
_shelx_estimated_absorpt_t_min   0.856
_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
 C2A-C18A = C2A-C17A
 1.54 with sigma of 0.02
 C2A-C3A = C3B-C2B = C4B-C3B
 1.54 with sigma of 0.01
 C26B-C25B \\sim C26C-C25B
 with sigma of 0.02
 C27B-C26B \\sim C27C-C26C
 with sigma of 0.02
 C28C-C27C \\sim C28B-C27B
 with sigma of 0.02
 C29B-C28C \\sim C29B-C28B
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C2A) = Uanis(C2)
Uanis(C14) = Uanis(C19A)
Uanis(C13) = Uanis(C16A)
Uanis(C15) = Uanis(C20A)
Uanis(C17A) = Uanis(C18)
Uanis(N1) = Uanis(N1A)
Uanis(C1A) = Uanis(C1)
Uanis(C23A) = Uanis(C23)
Uanis(C24A) = Uanis(C24)
Uanis(C10) = Uanis(C4A)
Uanis(C17) = Uanis(C18A)
Uanis(C14A) = Uanis(C11)
Uanis(C12) = Uanis(C15A)
Uanis(C11A) = Uanis(C21)
Uanis(C6A) = Uanis(C4)
Uanis(C26B) = Uanis(C26C)
Uanis(C27B) = Uanis(C27C)
Uanis(C28B) = Uanis(C28C)
Uanis(C10C) = Uanis(C10B)
Uanis(C9C) = Uanis(C9B)
Uanis(C13C) = Uanis(C13B)
Uanis(C6C) = Uanis(C6B)
Uanis(C14C) = Uanis(C14B)
Uanis(C5B) = Uanis(C5C)
Uanis(C4C) = Uanis(C4B)
Uanis(C19C) = Uanis(C19B)
Uanis(C20B) = Uanis(C20C)
Uanis(N1C) = Uanis(N1B)
Uanis(C2B) = Uanis(C2C)
4. Rigid body (RIGU) restrains
 C12A, C11A, C13A, C6A, C7A, C8A, C9A, C5A, C10A, N1A, C24A, C23A, C1A, C4A,
 C21A, C22A, C16A, C15A, C14A, C20A, C19A, C17A, C2A, C18A, C3A, C25, C24B
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.004
 C14B, C15B, C16B, C14C, C16C, C15C, C5B, C7B, C8B, C9B, C10B, C5C, C7C, C8C,
 C9C, C10C, C6C, C6B, C11B, C12B, C11C, C12C, C13B, C13C, N1B, N1C
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.004
 N1B, N1C
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.004
5. Same fragment restrains
{N1, C1, C2, C3, C4, C5, C6, C7, C8, C9, C10, C11, C12, C13, C14, C15, C16,
C17, C18, C19, C20, C21, C22, C23, C24} sigma for 1-2: 0.02, 1-3: 0.04
as
{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}
6. Others
 Sof(H29A)=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(H12G)=Sof(H12H)=Sof(H12I)=
 Sof(C13A)=Sof(H13G)=Sof(H13H)=Sof(H13I)=Sof(C14A)=Sof(H14A)=Sof(C15A)=
 Sof(H15G)=Sof(H15H)=Sof(H15I)=Sof(C16A)=Sof(H16G)=Sof(H16H)=Sof(H16I)=
 Sof(C17A)=Sof(H17G)=Sof(H17H)=Sof(H17I)=Sof(C18A)=Sof(H18G)=Sof(H18H)=
 Sof(H18I)=Sof(C19A)=Sof(H19E)=Sof(H19F)=Sof(C20A)=Sof(H20G)=Sof(H20H)=
 Sof(H20I)=Sof(C21A)=Sof(H21E)=Sof(H21F)=Sof(C22A)=Sof(H22G)=Sof(H22H)=
 Sof(H22I)=Sof(C23A)=Sof(C24A)=Sof(C26C)=Sof(H26C)=Sof(C27C)=Sof(H27C)=
 Sof(C28C)=Sof(H28C)=1-FVAR(1)
 Sof(H29B)=Sof(N1)=Sof(C1)=Sof(C2)=Sof(C3)=Sof(H3A)=Sof(H3B)=Sof(C4)=Sof(C5)=
 Sof(C6)=Sof(C7)=Sof(H7)=Sof(C8)=Sof(H8)=Sof(C9)=Sof(H9)=Sof(C10)=Sof(C11)=
 Sof(H11)=Sof(C12)=Sof(H12D)=Sof(H12E)=Sof(H12F)=Sof(C13)=Sof(H13D)=Sof(H13E)=
 Sof(H13F)=Sof(C14)=Sof(H14)=Sof(C15)=Sof(H15D)=Sof(H15E)=Sof(H15F)=Sof(C16)=
 Sof(H16D)=Sof(H16E)=Sof(H16F)=Sof(C17)=Sof(H17D)=Sof(H17E)=Sof(H17F)=Sof(C18)=
 Sof(H18D)=Sof(H18E)=Sof(H18F)=Sof(C19)=Sof(H19C)=Sof(H19D)=Sof(C20)=Sof(H20D)=
 Sof(H20E)=Sof(H20F)=Sof(C21)=Sof(H21C)=Sof(H21D)=Sof(C22)=Sof(H22D)=Sof(H22E)=
 Sof(H22F)=Sof(C23)=Sof(C24)=Sof(C26B)=Sof(H26B)=Sof(C27B)=Sof(H27B)=Sof(C28B)=
 Sof(H28B)=FVAR(1)
 Sof(N1C)=Sof(C2C)=Sof(C3C)=Sof(H3CA)=Sof(H3CB)=Sof(C4C)=Sof(C5C)=Sof(C10C)=
 Sof(C9C)=Sof(H9C)=Sof(C8C)=Sof(H8C)=Sof(C7C)=Sof(H7C)=Sof(C6C)=Sof(C11C)=
 Sof(H11C)=Sof(C13C)=Sof(H13J)=Sof(H13K)=Sof(H13L)=Sof(C14C)=Sof(H14C)=
 Sof(C16C)=Sof(H16J)=Sof(H16K)=Sof(H16L)=Sof(C17C)=Sof(H17J)=Sof(H17K)=
 Sof(H17L)=Sof(C18C)=Sof(H18J)=Sof(H18K)=Sof(H18L)=Sof(C20C)=Sof(H20J)=
 Sof(H20K)=Sof(H20L)=Sof(C15C)=Sof(H15J)=Sof(H15K)=Sof(H15L)=Sof(C12C)=
 Sof(H12J)=Sof(H12K)=Sof(H12L)=Sof(C21C)=Sof(H21G)=Sof(H21H)=Sof(C19C)=
 Sof(H19G)=Sof(H19H)=Sof(C22C)=Sof(H22J)=Sof(H22K)=Sof(H22L)=1-FVAR(2)
 Sof(N1B)=Sof(C2B)=Sof(C3B)=Sof(H3BA)=Sof(H3BB)=Sof(C4B)=Sof(C5B)=Sof(C6B)=
 Sof(C7B)=Sof(H7B)=Sof(C8B)=Sof(H8B)=Sof(C9B)=Sof(H9B)=Sof(C10B)=Sof(C11B)=
 Sof(H11B)=Sof(C12B)=Sof(H12A)=Sof(H12B)=Sof(H12C)=Sof(C13B)=Sof(H13A)=
 Sof(H13B)=Sof(H13C)=Sof(C14B)=Sof(H14B)=Sof(C15B)=Sof(H15A)=Sof(H15B)=
 Sof(H15C)=Sof(C16B)=Sof(H16A)=Sof(H16B)=Sof(H16C)=Sof(C17B)=Sof(H17A)=
 Sof(H17B)=Sof(H17C)=Sof(C18B)=Sof(H18A)=Sof(H18B)=Sof(H18C)=Sof(C19B)=
 Sof(H19A)=Sof(H19B)=Sof(C20B)=Sof(H20A)=Sof(H20B)=Sof(H20C)=Sof(C21B)=
 Sof(H21A)=Sof(H21B)=Sof(C22B)=Sof(H22A)=Sof(H22B)=Sof(H22C)=FVAR(2)
7.a Ternary CH refined with riding coordinates:
 C11B(H11B), C14B(H14B), C11(H11), C14(H14), C11A(H11A), C14A(H14A),
 C11C(H11C), C14C(H14C)
7.b Secondary CH2 refined with riding coordinates:
 C3B(H3BA,H3BB), C19B(H19A,H19B), C21B(H21A,H21B), C3(H3A,H3B), C19(H19C,H19D),
  C21(H21C,H21D), C3A(H3AA,H3AB), C19A(H19E,H19F), C21A(H21E,H21F), C3C(H3CA,
 H3CB), C21C(H21G,H21H), C19C(H19G,H19H)
7.c Aromatic/amide H refined with riding coordinates:
 C7B(H7B), C8B(H8B), C9B(H9B), C26(H26), C27(H27), C28(H28), C29(H29),
 C29B(H29B), C29B(H29A), C30(H30), C30B(H30B), C7(H7), C8(H8), C9(H9),
 C26B(H26B), C27B(H27B), C28B(H28B), C7A(H7A), C8A(H8A), C9A(H9A), C26C(H26C),
 C27C(H27C), C28C(H28C), C9C(H9C), C8C(H8C), C7C(H7C)
7.d Fitted hexagon refined as free rotating group:
 C5C(C10C,C9C,C8C,C7C,C6C)
7.e Idealised Me refined as rotating group:
 C12B(H12A,H12B,H12C), C13B(H13A,H13B,H13C), C15B(H15A,H15B,H15C), C16B(H16A,
 H16B,H16C), C17B(H17A,H17B,H17C), C18B(H18A,H18B,H18C), C20B(H20A,H20B,H20C),
 C22B(H22A,H22B,H22C), C12(H12D,H12E,H12F), C13(H13D,H13E,H13F), C15(H15D,H15E,
 H15F), C16(H16D,H16E,H16F), C17(H17D,H17E,H17F), C18(H18D,H18E,H18F), C20(H20D,
 H20E,H20F), C22(H22D,H22E,H22F), C12A(H12G,H12H,H12I), C13A(H13G,H13H,H13I),
 C15A(H15G,H15H,H15I), C16A(H16G,H16H,H16I), C17A(H17G,H17H,H17I), C18A(H18G,
 H18H,H18I), C20A(H20G,H20H,H20I), C22A(H22G,H22H,H22I), C13C(H13J,H13K,H13L),
 C16C(H16J,H16K,H16L), C17C(H17J,H17K,H17L), C18C(H18J,H18K,H18L), C20C(H20J,
 H20K,H20L), C15C(H15J,H15K,H15L), C12C(H12J,H12K,H12L), C22C(H22J,H22K,H22L)
;
_shelx_res_checksum              13093
_shelx_hkl_checksum              21236
_olex2_submission_special_instructions 'No special instructions were received'