Isolation of a chiral anthracene cation radical: X-ray crystallography and computational interrogation of its racemization.
Ivanov, Maxim V.; Thakur, Khushabu; Bhatnagar, Anshul; Rathore, Rajendra; Chemical communications (Cambridge, England) 53 (2017) 2748–2751; doi:10.1039/c6cc10307c

data_7119641
_publ_section_title
;
 Isolation of a chiral anthracene cation radical: X-ray crystallography
 and computational interrogation of its racemization.
;
_journal_issue                   18
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              2748
_journal_page_last               2751
_journal_paper_doi               10.1039/c6cc10307c
_journal_volume                  53
_journal_year                    2017
_chemical_absolute_configuration ad
_chemical_formula_moiety         'Cl6 Sb, C30 H22'
_chemical_formula_sum            'C30 H22 Cl6 Sb'
_chemical_formula_weight         716.93
_chemical_name_systematic
;
 ? 
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           43
_space_group_name_Hall           'F 2 -2d'
_space_group_name_H-M_alt        'F d d 2'
_symmetry_space_group_name_Hall  'F 2 -2d'
_symmetry_space_group_name_H-M   'F d d 2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2015-09-09
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2017-01-03 deposited with the CCDC.
2017-02-09 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   29.7613(10)
_cell_length_b                   18.2178(6)
_cell_length_c                   10.1451(3)
_cell_measurement_reflns_used    5863
_cell_measurement_temperature    99.95(10)
_cell_measurement_theta_max      73.4350
_cell_measurement_theta_min      5.1120
_cell_volume                     5500.5(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
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_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.95(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3756
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details
;
  1 omega  -49.00   35.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.2737   37.0000  -60.0000 84

  2 omega  -75.00   37.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.2737   77.0000  -30.0000 112

  3 omega -124.00  -79.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.2737  -99.0000    0.0000 45

  4 omega   15.00  117.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       41.2737   37.0000 -150.0000 102

  5 omega   30.00   90.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.2878  -30.0000  -60.0000 60

  6 omega   94.00  178.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.2878  125.0000  120.0000 84

  7 omega   30.00   90.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.2878  -30.0000   90.0000 60

  8 omega   30.00   90.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.2878  -30.0000   30.0000 60

  9 omega   24.00  109.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.2878  -94.0000  -90.0000 85

 10 omega   81.00  178.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.2878   45.0000  -30.0000 97

 11 omega   94.00  178.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.2878  125.0000  -30.0000 84

 12 omega   34.00   98.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.2878  -45.0000 -120.0000 64

 13 omega -120.00   -8.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.2737  -77.0000  120.0000 112

 14 omega -115.00  -12.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.2737  -57.0000    0.0000 103

 15 omega -120.00   -8.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.2737  -77.0000  -90.0000 112

 16 omega   23.00   99.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       41.2737 -125.0000  150.0000 76

 17 omega   78.00  178.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.2878   30.0000 -150.0000 100

 18 omega   24.00  109.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.2878  -94.0000   90.0000 85

 19 omega   47.00  178.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.2878   15.0000  120.0000 131

 20 omega   81.00  106.00   1.0000   16.0000
omega____ theta____ kappa____ phi______ frames
    -      108.2878   45.0000  -90.0000 25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0253019000
_diffrn_orient_matrix_UB_12      0.0644827000
_diffrn_orient_matrix_UB_13      -0.0647027000
_diffrn_orient_matrix_UB_21      0.0439745000
_diffrn_orient_matrix_UB_22      0.0445092000
_diffrn_orient_matrix_UB_23      -0.0051190000
_diffrn_orient_matrix_UB_31      0.0102967000
_diffrn_orient_matrix_UB_32      -0.0318163000
_diffrn_orient_matrix_UB_33      -0.1372652000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0794
_diffrn_reflns_av_unetI/netI     0.0499
_diffrn_reflns_limit_h_max       36
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            12580
_diffrn_reflns_theta_full        72.00
_diffrn_reflns_theta_max         73.87
_diffrn_reflns_theta_min         5.21
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    13.475
_exptl_absorpt_correction_T_max  0.845
_exptl_absorpt_correction_T_min  0.196
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Numerical absorption correction based on gaussian integration over
            a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'dark blue'
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    1.731
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             2840
_exptl_crystal_size_max          0.2931
_exptl_crystal_size_mid          0.0883
_exptl_crystal_size_min          0.0132
_refine_diff_density_max         2.169
_refine_diff_density_min         -0.802
_refine_diff_density_rms         0.299
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.051(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     168
_refine_ls_number_reflns         2540
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.046
_refine_ls_R_factor_all          0.0418
_refine_ls_R_factor_gt           0.0389
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0597P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0943
_refine_ls_wR_factor_ref         0.0966
_reflns_number_gt                2368
_reflns_number_total             2540
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c6cc10307c2.cif
_cod_data_source_block           raj25s
_cod_depositor_comments
'Adding full bibliography for 7119641--7119642.cif.'
_cod_database_code               7119641
_chemical_oxdiff_formula         'C30 H22 Sb Cl6'
_reflns_odcompleteness_completeness 100.00
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C15(H15A,H15B)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C5(H5), C6(H6), C10(H10), C11(H11), C12(H12), C13(H13)
;
_olex2_date_sample_submission    2015-09-08
_olex2_submission_special_instructions 'No special instructions were received'