Flavanthrone ‒ a new ligand with accessible radical anion and dianion states: preparation of zwitterionic {(Cp2V)2(flavanthrone)} and {(Cp2V)2(chloranil)} complexes
Konarev, Dmitri V.; Andronov, Mikhail G.; Batov, Mikhail S.; Kuzmin, Alexey V.; Khasanov, Salavat S.; Shestakov, Alexander F.; Otsuka, Akihiro; Yamochi, Hideki; Kitagawa, Hiroshi; Lyubovskaya, Rimma N.; New Journal of Chemistry 44 (2020) 10849–10858; doi:10.1039/D0NJ01208D

data_7059658
_publ_section_title
;
 Flavanthrone -- a new ligand with accessible radical anion and dianion
 states: preparation of zwitterionic {(Cp2V)2(flavanthrone)} and
 {(Cp2V)2(chloranil)} complexes
;
_journal_issue                   26
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              10849
_journal_page_last               10858
_journal_paper_doi               10.1039/D0NJ01208D
_journal_volume                  44
_journal_year                    2020
_chemical_compound_source        no
_chemical_formula_moiety         '2(C16 H36 P), C28 H12 N2 O2'
_chemical_formula_sum            'C60 H84 N2 O2 P2'
_chemical_formula_weight         927.23
_chemical_melting_point          ?
_chemical_name_common            no
_chemical_name_systematic
'dianion salt of flavanthrone with tetrabutylphosphonium cations'
_chemical_properties_physical
Air-sensitive,Moisture-sensitive,Oxygen-sensitive
_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     iterative
_atom_sites_solution_secondary   difmap
_audit_creation_date             2020-01-15
_audit_creation_method
;
Olex2 1.3
(compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003)
;
_audit_update_record
;
2020-02-22 deposited with the CCDC.	2020-05-18 downloaded from the CCDC.
;
_cell_angle_alpha                80.100(4)
_cell_angle_beta                 73.741(5)
_cell_angle_gamma                87.212(4)
_cell_formula_units_Z            1
_cell_length_a                   10.0315(5)
_cell_length_b                   11.1650(5)
_cell_length_c                   12.4225(6)
_cell_measurement_reflns_used    3218
_cell_measurement_temperature    113(2)
_cell_measurement_theta_max      28.8850
_cell_measurement_theta_min      2.1050
_cell_volume                     1315.81(11)
_computing_cell_refinement       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.67a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve 1.3 (Bourhis et al., 2015)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      113(8)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2283
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.836
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w    -17.00  75.00   1.00  120.00    --   11.89  57.00 -60.00   92
  2  \w    -88.00 -40.00   1.00  120.00    --  -12.05 -37.00   0.00   48
  3  \w    -22.00  15.00   1.00  120.00    --  -12.05 -57.00 -90.00   37
  4  \w    -60.00  -3.00   1.00  120.00    --  -12.05 -57.00  30.00   57
  5  \w    -34.00  61.00   1.00  120.00    --  -12.05  57.00 150.00   95
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, AtlasS2, Gemini'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0721831000
_diffrn_orient_matrix_UB_12      -0.0073154000
_diffrn_orient_matrix_UB_13      0.0267617000
_diffrn_orient_matrix_UB_21      -0.0091747000
_diffrn_orient_matrix_UB_22      0.0638738000
_diffrn_orient_matrix_UB_23      -0.0110518000
_diffrn_orient_matrix_UB_31      -0.0114260000
_diffrn_orient_matrix_UB_32      -0.0049015000
_diffrn_orient_matrix_UB_33      -0.0528754000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0304
_diffrn_reflns_av_unetI/netI     0.0601
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.836
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            11636
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.836
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.584
_diffrn_reflns_theta_min         3.464
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.127
_exptl_absorpt_correction_T_max  0.997
_exptl_absorpt_correction_T_min  0.991
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.67a (Rigaku Oxford Diffraction, 2019)
Analytical numeric absorption correction using a multifaceted crystal
model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'metallic dark black'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.170
_exptl_crystal_description       block
_exptl_crystal_F_000             504
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: o-dichlorobenzene/n-hexane'
_exptl_crystal_size_max          0.212
_exptl_crystal_size_mid          0.105
_exptl_crystal_size_min          0.068
_refine_diff_density_max         0.897
_refine_diff_density_min         -0.387
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     372
_refine_ls_number_reflns         6173
_refine_ls_number_restraints     350
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.1089
_refine_ls_R_factor_gt           0.0705
_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^)+(0.0673P)^2^+1.1589P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1550
_refine_ls_wR_factor_ref         0.1795
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4254
_reflns_number_total             6173
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0nj01208d2.cif
_cod_data_source_block           Flavanthrone2Bu4P
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_chemical_melting_point' value 'not measured' was changed
to '?' -- the value is undefined or not given.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 

 Adding full bibliography for 7059654--7059658.cif.

 Adding full bibliography for 7059654--7059658.cif.
;
_cod_original_cell_volume        1315.80(12)
_cod_database_code               7059658
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C60  H84  N2  O2  P2 '
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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
 P201-C213 \\sim P201-C305
 with sigma of 0.02
 C213-C214 \\sim C305-C306
 with sigma of 0.02
 C214-C215 \\sim C306-C307
 with sigma of 0.02
 C215-C216 \\sim C307-C308
 with sigma of 0.02
 P201-C214 \\sim P201-C306
 with sigma of 0.04
 C213-C215 \\sim C305-C307
 with sigma of 0.04
 C214-C216 \\sim C306-C308
 with sigma of 0.04
 P201-C205 \\sim P201-C301
 with sigma of 0.02
 C205-C206 \\sim C301-C302
 with sigma of 0.02
 C206-C207 \\sim C302-C303
 with sigma of 0.02
 C207-C208 \\sim C303-C304
 with sigma of 0.02
 P201-C206 \\sim P201-C302
 with sigma of 0.04
 C205-C207 \\sim C301-C303
 with sigma of 0.04
 C206-C208 \\sim C302-C304
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
C213 \\sim C214 \\sim C215 \\sim C216 \\sim C305 \\sim C306 \\sim C307 \\sim
C308: within 5A with sigma of 0.02 and sigma for terminal atoms of 0.04 within
5A
C205 \\sim C206 \\sim C207 \\sim C208 \\sim C301 \\sim C302 \\sim C303 \\sim
C304: within 5A with sigma of 0.02 and sigma for terminal atoms of 0.04 within
5A
Uanis(C305) = Uanis(C213)
4. Others
 Sof(C305)=Sof(H30J)=Sof(H30K)=Sof(C306)=Sof(H30L)=Sof(H30M)=Sof(C307)=
 Sof(H30N)=Sof(H30O)=Sof(C308)=Sof(H30P)=Sof(H30Q)=Sof(H30R)=1-FVAR(1)
 Sof(C213)=Sof(H21H)=Sof(H21I)=Sof(C214)=Sof(H21J)=Sof(H21K)=Sof(C215)=
 Sof(H21L)=Sof(H21M)=Sof(C216)=Sof(H21N)=Sof(H21O)=Sof(H21P)=FVAR(1)
 Sof(C301)=Sof(H30A)=Sof(H30B)=Sof(C302)=Sof(H30C)=Sof(H30D)=Sof(C303)=
 Sof(H30E)=Sof(H30F)=Sof(C304)=Sof(H30G)=Sof(H30H)=Sof(H30I)=1-FVAR(2)
 Sof(C205)=Sof(H20L)=Sof(H20M)=Sof(C206)=Sof(H20N)=Sof(H20O)=Sof(C207)=
 Sof(H20P)=Sof(H20Q)=Sof(C208)=Sof(H20R)=Sof(H20S)=Sof(H20T)=FVAR(2)
5.a Secondary CH2 refined with riding coordinates:
 C201(H20A,H20B), C202(H20C,H20D), C203(H20E,H20F), C209(H20J,H20K), C210(H21A,
 H21B), C211(H21C,H21D), C205(H20L,H20M), C206(H20N,H20O), C207(H20P,H20Q),
 C213(H21H,H21I), C214(H21J,H21K), C215(H21L,H21M), C301(H30A,H30B), C302(H30C,
 H30D), C303(H30E,H30F), C305(H30J,H30K), C306(H30L,H30M), C307(H30N,H30O)
5.b Aromatic/amide H refined with riding coordinates:
 C101(H101), C102(H102), C106(H106), C107(H107), C108(H108), C109(H109)
5.c Idealised Me refined as rotating group:
 C204(H20G,H20H,H20I), C212(H21E,H21F,H21G), C208(H20R,H20S,H20T), C216(H21N,
 H21O,H21P), C304(H30G,H30H,H30I), C308(H30P,H30Q,H30R)
;
_shelx_res_checksum              39078
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.081
_oxdiff_exptl_absorpt_empirical_full_min 0.918