Tuning the redox profile of the 6,6'-biazulenic platform through functionalization along its molecular axis.
Kelsey, Shaun R.; Griaznov, Georgii; Spaeth, Andrew D.; Janzen, Daron E.; Douglas, Justin T.; Thompson, Ward H.; Barybin, Mikhail V.; Chemical communications (Cambridge, England) 60 (2024) 5213–5216; doi:10.1039/d4cc00656a

data_7132969
_publ_section_title
;
 Tuning the redox profile of the 6,6'-biazulenic platform through
 functionalization along its molecular axis.
;
_journal_issue                   39
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              5213
_journal_page_last               5216
_journal_paper_doi               10.1039/d4cc00656a
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'C32 H28 Cl2 O8'
_chemical_formula_sum            'C32 H28 Cl2 O8'
_chemical_formula_weight         611.44
_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             2022-10-04
_audit_creation_method
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_audit_update_record
;
2023-10-12 deposited with the CCDC.	2024-04-15 downloaded from the CCDC.
;
_cell_angle_alpha                96.395(7)
_cell_angle_beta                 99.389(7)
_cell_angle_gamma                117.914(8)
_cell_formula_units_Z            2
_cell_length_a                   9.9510(8)
_cell_length_b                   10.5842(9)
_cell_length_c                   14.9945(12)
_cell_measurement_reflns_used    5126
_cell_measurement_temperature    173.15
_cell_measurement_theta_max      32.4000
_cell_measurement_theta_min      2.2320
_cell_volume                     1344.5(2)
_computing_cell_refinement       'CrysAlisPro 1.171.42.64a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.64a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.64a (Rigaku OD, 2022)'
_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    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      173.15
_diffrn_detector                 'CCD plate'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.983
_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    -74.00 119.00   1.00    7.00    --   30.00  54.00 120.00  193
  2  \w    -74.00 119.00   1.00    7.00    --   30.00  54.00-120.00  193
  3  \w    -74.00 112.00   1.00    7.00    --   30.00  54.00 -30.00  186
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini (ROW)'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0726122000
_diffrn_orient_matrix_UB_12      0.0360223000
_diffrn_orient_matrix_UB_13      -0.0123410000
_diffrn_orient_matrix_UB_21      -0.0186220000
_diffrn_orient_matrix_UB_22      0.0531216000
_diffrn_orient_matrix_UB_23      -0.0136413000
_diffrn_orient_matrix_UB_31      0.0361045000
_diffrn_orient_matrix_UB_32      0.0437229000
_diffrn_orient_matrix_UB_33      0.0455220000
_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  0.0331
_diffrn_reflns_av_unetI/netI     0.0471
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            18156
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.508
_diffrn_reflns_theta_min         2.230
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_exptl_absorpt_coefficient_mu    0.298
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85925
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.42.64a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'dark red'
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.510
_exptl_crystal_description       block
_exptl_crystal_F_000             636
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: pentane'
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.490
_refine_diff_density_min         -0.591
_refine_diff_density_rms         0.073
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     383
_refine_ls_number_reflns         8070
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.062
_refine_ls_R_factor_all          0.0753
_refine_ls_R_factor_gt           0.0527
_refine_ls_shift/su_max          0.001
_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^+0.5097P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1357
_refine_ls_wR_factor_ref         0.1598
_reflns_Friedel_coverage         0.000
_reflns_number_gt                5915
_reflns_number_total             8070
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc00656a2.cif
_cod_data_source_block           3a
_cod_depositor_comments          'Adding full bibliography for 7132969.cif.'
_cod_database_code               7132969
_publ_section.title
;Tuning the redox profile of the 6,6'-biazulenic platform
 through functionalization along its molecular axis and 
the surprising structural influence of dichloro substitution
;
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         C32H28Cl2O8
_chemical_oxdiff_usercomment     'Misha UK sample SK-3-178'
_reflns_odcompleteness_completeness 99.96
_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.a Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B), C12(H12A,H12B), C21(H21A,H21B), C15(H15A,H15B)
2.b Aromatic/amide H refined with riding coordinates:
 C4(H4), C8(H8), C5(H5), C8'(H8'), C7'(H7'), C7(H7), C4'(H4'), C5'(H5')
2.c Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C19(H19A,H19B,H19C), C22(H22A,H22B,H22C), C16(H16A,H16B,
 H16C)
;
_olex2_exptl_crystal_mounting_method 'Mitigen micromount'
_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 1.334
_oxdiff_exptl_absorpt_empirical_full_min 0.787