2-(9,10-Anthraquinon-2-yl)-4,4,5,5-tetramethyl-4,5-dihydro-1H-imidazole-3-oxide-1-oxyl: polymorphism in a conjugated anthraquinone-substituted nitronylnitroxide
Handan Akpinar; John A. Schlueter; Paul M. Lahti; Chem.Commun. 49 (2013) 3345–; doi:10.1039/c3cc41075g

data_7109086
_publ_section_title
;
 2-(9,10-Anthraquinon-2-yl)-4,4,5,5-tetramethyl-4,5-dihydro-1H-imidazole-3-oxide-1-oxyl:
 polymorphism in a conjugated anthraquinone-substituted nitronylnitroxide
;
_journal_name_full               Chem.Commun.
_journal_page_first              3345
_journal_paper_doi               10.1039/c3cc41075g
_journal_volume                  49
_journal_year                    2013
_chemical_formula_moiety         'C21 H19 N2 O4'
_chemical_formula_sum            'C21 H19 N2 O4'
_chemical_formula_weight         363.38
_chemical_melting_point          481
_chemical_name_common
;
2-(9,10-Anthraquinon-2-yl)-4,4,5,5-tetramethyl-4,5-dihydro-1H-
imidazole-3-oxide-
;
_chemical_name_systematic
;
2-(9,10-Anthraquinon-2-yl)-4,4,5,5-tetramethyl-4,5-dihydro-1H-imidazole-3-oxide-1-oxyl
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      61
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           'manual editing of SHELXL-97 cif file'
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   7.2592(5)
_cell_length_b                   21.3199(14)
_cell_length_c                   22.2954(15)
_cell_measurement_reflns_used    3133
_cell_measurement_temperature    199(2)
_cell_measurement_theta_max      21.358
_cell_measurement_theta_min      2.644
_cell_volume                     3450.6(4)
_computing_cell_refinement       'APEX II v.2.2 (Bruker, 2007)'
_computing_data_collection       'APEX II v.2.2 (Bruker, 2007)'
_computing_data_reduction        'APEX II v.2.2 (Bruker, 2007)'
_computing_molecular_graphics    'Diamond 3.1a (Crystal Impact, 2005)'
_computing_publication_material  'SHELXTL (Bruker, 2006)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      199(2)
_diffrn_detector_area_resol_mean 83.33
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  '3-circle goniometer'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0680
_diffrn_reflns_av_sigmaI/netI    0.0327
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            27343
_diffrn_reflns_theta_full        24.81
_diffrn_reflns_theta_max         24.81
_diffrn_reflns_theta_min         1.83
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  0.7451
_exptl_absorpt_correction_T_min  0.6062
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, R. Blessing; 1995'
_exptl_crystal_colour            black
_exptl_crystal_density_diffrn    1.399
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1528
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.215
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       0.0016(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     245
_refine_ls_number_reflns         2974
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.0673
_refine_ls_R_factor_gt           0.0431
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[\s^2^(Fo^2^)+(0.0609P)^2^+1.6872P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1099
_refine_ls_wR_factor_ref         0.1258
_reflns_number_gt                2176
_reflns_number_total             2974
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c3cc41075g.txt
_cod_data_source_block           BAntQNN199K
_cod_database_code               7109086