Indanthrone dye revisited after sixty years
Kamil Kotwica; Piotr Bujak; Damian Wamil; Mariusz Materna; Lukasz Skorka; Piotr A. Gunka; Robert Nowakowski; Barbara Golec; Beata Luszczynska; Malgorzata Zagorska; Adam Pron; Chem.Commun. 50 (2014) 11543–; doi:10.1039/C4cc04778H

data_7115686
_publ_section_title
;
 Indanthrone dye revisited after sixty years
;
_journal_name_full               Chem.Commun.
_journal_page_first              11543
_journal_paper_doi               10.1039/C4cc04778H
_journal_volume                  50
_journal_year                    2014
_chemical_formula_moiety         'C60 H80 N2 O4'
_chemical_formula_sum            'C60 H80 N2 O4'
_chemical_formula_weight         893.26
_chemical_name_systematic
;
 5,9,14,18-tetraoctyloxy-dinaphto[2,3-a:2,3-h]phenazine
;
_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
_atom_sites_solution_primary     direct
_audit_creation_date             2014-05-20
_audit_creation_method
;
Olex2 1.2-beta
(compiled 2014.03.20 svn.r2918 for OlexSys, GUI svn.r4816)
;
_cell_angle_alpha                69.7564(13)
_cell_angle_beta                 88.9555(11)
_cell_angle_gamma                87.1772(12)
_cell_formula_units_Z            2
_cell_length_a                   9.93781(14)
_cell_length_b                   15.1528(2)
_cell_length_c                   17.8125(2)
_cell_measurement_reflns_used    19532
_cell_measurement_temperature    100
_cell_measurement_theta_max      32.6980
_cell_measurement_theta_min      2.3330
_cell_volume                     2513.57(6)
_computing_cell_refinement
'CrysAlisPro, Agilent Technologies, Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET) (compiled Jan 14 2014,18:38:05)'
_computing_data_collection
'CrysAlisPro, Agilent Technologies, Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET) (compiled Jan 14 2014,18:38:05)'
_computing_data_reduction
'CrysAlisPro, Agilent Technologies, Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET) (compiled Jan 14 2014,18:38:05)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3347
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.938
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0113305000
_diffrn_orient_matrix_UB_12      0.0496179000
_diffrn_orient_matrix_UB_13      -0.0139266000
_diffrn_orient_matrix_UB_21      -0.0383454000
_diffrn_orient_matrix_UB_22      -0.0024722000
_diffrn_orient_matrix_UB_23      -0.0323544000
_diffrn_orient_matrix_UB_31      -0.0592273000
_diffrn_orient_matrix_UB_32      -0.0051331000
_diffrn_orient_matrix_UB_33      0.0236763000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0420
_diffrn_reflns_av_unetI/netI     0.0320
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.938
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            99579
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.938
_diffrn_reflns_theta_full        30.000
_diffrn_reflns_theta_max         32.847
_diffrn_reflns_theta_min         2.052
_diffrn_source                   'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.82921
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31(release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05) Empirical absorption correction
using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.180
_exptl_crystal_F_000             972
_exptl_crystal_size_max          0.4328
_exptl_crystal_size_mid          0.2486
_exptl_crystal_size_min          0.0624
_refine_diff_density_max         0.518
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.058
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.024
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     599
_refine_ls_number_reflns         17538
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.024
_refine_ls_R_factor_all          0.0809
_refine_ls_R_factor_gt           0.0513
_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^)+(0.0731P)^2^+0.6524P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1326
_refine_ls_wR_factor_ref         0.1543
_reflns_Friedel_coverage         0.000
_reflns_number_gt                12156
_reflns_number_total             17538
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c4cc04778h2.cif
_cod_data_source_block           pg54
_cod_original_cell_volume        2513.57(7)
_cod_database_code               7115686
_shelxl_version_number           2014-1
_chemical_oxdiff_formula         'C60 H80 N2 O4'
_reflns_odcompleteness_completeness 99.98
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.44
_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.a Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C16(H16A,H16B), C17(H17A,H17B), C18(H18A,H18B), C19(H19A,
 H19B), C20(H20A,H20B), C21(H21A,H21B), C23(H23A,H23B), C24(H24A,H24B),
 C25(H25A,H25B), C26(H26A,H26B), C27(H27A,H27B), C28(H28A,H28B), C29(H29A,H29B),
  C45(H45A,H45B), C46(H46A,H46B), C47(H47A,H47B), C48(H48A,H48B), C49(H49A,
 H49B), C50(H50A,H50B), C51(H51A,H51B), C53(H53A,H53B), C54(H54A,H54B),
 C55(H55A,H55B), C56(H56A,H56B), C57(H57A,H57B), C58(H58A,H58B), C59(H59A,H59B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C4(H4), C10(H10), C11(H11), C31(H31), C32(H32),
 C33(H33), C34(H34), C40(H40), C41(H41)
2.c Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C30(H30A,H30B,H30C), C52(H52A,H52B,H52C), C60(H60A,H60B,
 H60C)
;
_shelx_res_checksum              10135
_shelx_hkl_checksum              82203