Photocrystallisation of the 2C–2′C dimer of a triphenylimidazolyl radical
Edkins, Robert M.; Probert, Michael R.; Robertson, Craig M.; Howard, Judith A. K.; Beeby, Andrew; RSC Adv. 4 (2014) 5351–; doi:10.1039/C3RA43892A

data_7239242
_publ_section_title
;
 Photocrystallisation of the 2C--2&#x2032;C dimer of a triphenylimidazolyl
 radical
;
_journal_issue                   11
_journal_name_full               'RSC Adv.'
_journal_page_first              5351
_journal_paper_doi               10.1039/C3RA43892A
_journal_volume                  4
_journal_year                    2014
_chemical_formula_moiety         'C66 H54 N4'
_chemical_formula_sum            'C66 H54 N4'
_chemical_formula_weight         903.13
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2013-11-27
_audit_creation_method
;
  Olex2 1.2-beta
  (compiled 2012.11.06 svn.r2526, GUI svn.r4372)
;
_cell_angle_alpha                86.646(6)
_cell_angle_beta                 82.585(6)
_cell_angle_gamma                70.912(5)
_cell_formula_units_Z            2
_cell_length_a                   10.503(4)
_cell_length_b                   14.511(6)
_cell_length_c                   19.926(8)
_cell_measurement_reflns_used    728
_cell_measurement_temperature    100
_cell_measurement_theta_max      21.90
_cell_measurement_theta_min      2.45
_cell_volume                     2845(2)
_computing_cell_refinement       'SAINT v8.27A (Bruker, 2012)'
_computing_data_collection       'APEX2 v2012.10-0 (Bruker, 2012)'
_computing_data_reduction        'SAINT v8.27A (Bruker, 2012)'
_computing_molecular_graphics
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution
;
XM, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_diffrn_ambient_temperature      100
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean 0.0350
_diffrn_detector_type            'Rigaku Saturn724+'
_diffrn_measured_fraction_theta_full 0.463
_diffrn_measured_fraction_theta_max 0.806
_diffrn_measurement_device       'CrystalLogic Kappa (4 circle)'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_collimation    '0.3 x 1.5 Double Pinhole'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_wavelength     0.6889
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_unetI/netI     0.1486
_diffrn_reflns_Laue_measured_fraction_full 0.463
_diffrn_reflns_Laue_measured_fraction_max 0.806
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            4788
_diffrn_reflns_point_group_measured_fraction_full 0.463
_diffrn_reflns_point_group_measured_fraction_max 0.806
_diffrn_reflns_theta_full        24.415
_diffrn_reflns_theta_max         20.103
_diffrn_reflns_theta_min         1.738
_diffrn_source                   Synchrotron
_diffrn_source_type              'Undulator, I19, DLS, RAL'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.033
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'clear light green'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.054
_exptl_crystal_description       block
_exptl_crystal_F_000             956
_exptl_crystal_recrystallization_method
'Crystals were formed from hexane acetone mixture by solvent evaporation'
_exptl_crystal_size_max          0.07
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.218
_refine_diff_density_min         -0.209
_refine_diff_density_rms         0.046
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.898
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     541
_refine_ls_number_reflns         4782
_refine_ls_number_restraints     194
_refine_ls_restrained_S_all      0.884
_refine_ls_R_factor_all          0.1669
_refine_ls_R_factor_gt           0.0905
_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^)+(0.1509P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2219
_refine_ls_wR_factor_ref         0.2519
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2221
_reflns_number_total             4782
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c3ra43892a.txt
_cod_data_source_block           p-1
_cod_original_cell_volume        2845.6(19)
_cod_database_code               7239242
_shelxl_version_number           2013-3
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid bond restraints
 All non-hydrogen atoms
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
3.a Aromatic/amide H refined with riding coordinates:
 C11(H11), C10(H10), C8(H8), C7(H7), C15(H15), C16(H16), C18(H18), C19(H19),
 C29(H29), C28(H28), C27(H27), C26(H26), C25(H25), C31(H31), C32(H32), C33(H33),
  C34(H34), C35(H35), C7'(H7'), C8'(H8'), C10'(H10'), C11'(H11'), C15'(H15'),
 C16'(H16'), C18'(H18'), C19'(H19'), C25'(H25'), C26'(H26'), C27'(H27'),
 C28'(H28'), C29'(H29'), C31'(H31'), C32'(H32'), C33'(H33'), C34'(H34'),
 C35'(H35')
3.b Fitted hexagon refined as free rotating group:
 C6(C11,C10,C9,C8,C7), C14(C15,C16,C17,C18,C19), C24(C29,C28,C27,C26,C25),
 C30(C31,C32,C33,C34,C35), C6'(C7',C8',C9',C10',C11'), C14'(C15',C16',C17',C18',
 C19'), C24'(C25',C26',C27',C28',C29'), C30'(C31',C32',C33',C34',C35')
3.c Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C22(H22A,H22B,H22C), C23(H23A,H23B,H23C), C21'(H21D,H21E,
 H21F), C22'(H22D,H22E,H22F), C23'(H23D,H23E,H23F)
;
_shelx_res_checksum              66442
_shelx_hkl_checksum              12024