Efficient electrochemical synthesis of robust, densely functionalized water soluble quinones.
Gerken, James B.; Stamoulis, Alexios; Suh, Sung-Eun; Fischer, Nicholas D.; Kim, Yeon Jung; Guzei, Ilia A.; Stahl, Shannon S.; Chemical communications (Cambridge, England) 56 (2020) 1199–1202; doi:10.1039/c9cc08878d

data_7125670
_publ_section_title
;
 Efficient electrochemical synthesis of robust, densely functionalized
 water soluble quinones.
;
_journal_issue                   8
_journal_name_full
'Chemical communications (Cambridge, England)'
_journal_page_first              1199
_journal_page_last               1202
_journal_paper_doi               10.1039/c9cc08878d
_journal_volume                  56
_journal_year                    2020
_chemical_formula_moiety         '0.25(C56 H88 Na16 O68 S32)'
_chemical_formula_sum            'C14 H22 Na4 O17 S8'
_chemical_formula_weight         810.75
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2017-04-11
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_audit_update_record
;
2019-09-04 deposited with the CCDC.	2019-12-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 96.888(13)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   19.151(5)
_cell_length_b                   5.1130(16)
_cell_length_c                   29.210(7)
_cell_measurement_reflns_used    9956
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.5104
_cell_measurement_theta_min      2.4169
_cell_volume                     2839.6(13)
_computing_cell_refinement       'SAINT+ Ver. 2016.5-0 (Bruker-AXS, 2016)'
_computing_data_collection       'APEX3 Ver. 2016.5-0 (Bruker-AXS, 2016)'
_computing_data_reduction        'SAINT+ Ver. 2016.5-0 (Bruker-AXS, 2016)'
_computing_molecular_graphics    'OLEX2 (Dolomanov et al., 2009)'
_computing_publication_material  'OLEX2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2015b)'
_computing_structure_solution    'XT (Sheldrick, 2015a)'
_diffrn_ambient_temperature      100.01
_diffrn_detector                 'charge-coupled device (CCD) area detector'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'Bruker APEX II'
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX II Quazar'
_diffrn_measurement_method       '0.5\ \w and 0.5\ \f scans'
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_radiation_detector       'Bruker APEX II'
_diffrn_radiation_monochromator  'mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_reflns_av_R_equivalents  0.0364
_diffrn_reflns_av_unetI/netI     0.0181
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_number            30410
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.999
_diffrn_reflns_theta_min         1.404
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\ms'
_exptl_absorpt_coefficient_mu    0.767
_exptl_absorpt_correction_T_max  0.9848
_exptl_absorpt_correction_T_min  0.9325
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Krause et al., 2015) was used for absorption correction.'
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.896
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1656
_exptl_crystal_size_max          0.118
_exptl_crystal_size_mid          0.043
_exptl_crystal_size_min          0.036
_refine_diff_density_max         0.348
_refine_diff_density_min         -0.360
_refine_diff_density_rms         0.071
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     205
_refine_ls_number_reflns         2785
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          0.0344
_refine_ls_R_factor_gt           0.0289
_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^)+(0.0373P)^2^+5.2934P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0723
_refine_ls_wR_factor_ref         0.0746
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2438
_reflns_number_total             2785
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c9cc08878d2.cif
_cod_data_source_block           stahl230b
_cod_depositor_comments
'Adding full bibliography for 7125669--7125670.cif.'
_cod_database_code               7125670
_shelx_shelxl_version_number     2016/6
_shelx_estimated_absorpt_t_max   0.973
_shelx_estimated_absorpt_t_min   0.915
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
 At 1.5 times of:
  All O(H,H) groups
2. Restrained distances
 O2-H2B \\sim O2-H2A
 with sigma of 0.02
3.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B), C2(H2C,H2D), C6(H6A,H6B), C7(H7A,H7B)
;
_shelx_res_checksum              27828
_olex2_submission_special_instructions 'No special instructions were received'