Triptycene 1,2-Quinones and Quinols: Permeable Crystalline Redox-Active Molecular Solids.
Langis-Barsetti, Sophie; Maris, Thierry; Wuest, James D.; The Journal of organic chemistry 83 (2018) 15426–15437; doi:10.1021/acs.joc.8b02706

data_4034754
_publ_section_title
;
 Triptycene 1,2-Quinones and Quinols: Permeable Crystalline Redox-Active
 Molecular Solids.
;
_journal_issue                   24
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              15426
_journal_page_last               15437
_journal_paper_doi               10.1021/acs.joc.8b02706
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety         'C20 H10 O6, C4 H8 O'
_chemical_formula_sum            'C24 H18 O7'
_chemical_formula_weight         418.38
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2016-07-05
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                90
_cell_angle_beta                 93.856(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.2472(6)
_cell_length_b                   8.4518(3)
_cell_length_c                   12.4155(4)
_cell_measurement_reflns_used    9990
_cell_measurement_temperature    120
_cell_measurement_theta_max      60.572
_cell_measurement_theta_min      4.226
_cell_volume                     1910.40(11)
_computing_cell_refinement
;
SAINT (2013) V8.37A; Integration Software for Single Crystal Data.
Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_collection
;
APEX 2 (2013) Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_data_reduction
;
SAINT (2013) V8.37A; Integration Software for Single Crystal Data.
Bruker AXS Inc., Madison, WI 53719-1173.
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      120
_diffrn_detector                 'CMOS Area detector'
_diffrn_detector_area_resol_mean 10.24
_diffrn_detector_type            'Bruker Photon 100 CMOS Detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'k-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker Venture Metaljet'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_collimation    'Focusing mirrors'
_diffrn_radiation_monochromator  'Helios MX Mirror Optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0806
_diffrn_reflns_av_unetI/netI     0.0359
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            47522
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         60.682
_diffrn_reflns_theta_min         2.111
_diffrn_source                   'Metal Jet'
_diffrn_source_target            Ga
_diffrn_source_type              'Gallium Liquid Metal Jet Source'
_exptl_absorpt_coefficient_mu    0.577
_exptl_absorpt_correction_T_max  0.7519
_exptl_absorpt_correction_T_min  0.6797
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1034 before and 0.0811 after correction.
The Ratio of minimum to maximum transmission is 0.9040.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            'clear light red'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.455
_exptl_crystal_description       block
_exptl_crystal_F_000             872
_exptl_crystal_recrystallization_method 'crystallized in THF/hexane'
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.538
_refine_diff_density_min         -0.462
_refine_diff_density_rms         0.065
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     286
_refine_ls_number_reflns         4389
_refine_ls_number_restraints     36
_refine_ls_restrained_S_all      1.071
_refine_ls_R_factor_all          0.1010
_refine_ls_R_factor_gt           0.0737
_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^)+(0.0682P)^2^+2.7794P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1680
_refine_ls_wR_factor_ref         0.1853
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3237
_reflns_number_total             4389
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b02706_si_008.cif
_cod_data_source_block           jw18582
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_diffrn_radiation_probe' value 'X-ray' was changed to
'x-ray' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas 
;
_cod_database_code               4034754
_shelx_estimated_absorpt_t_max   0.961
_shelx_estimated_absorpt_t_min   0.929
_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 O(H) groups
2. Uiso/Uaniso restraints and constraints
C13 \\sim C14 \\sim C15 \\sim C16 \\sim C17 \\sim C18: within 2A with sigma of
0.005 and sigma for terminal atoms of 0.005
3.a Ternary CH refined with riding coordinates:
 C19(H19), C20(H20)
3.b Secondary CH2 refined with riding coordinates:
 C21(H21A,H21B), C22(H22A,H22B), C23(H23A,H23B), C24(H24A,H24B)
3.c Aromatic/amide H refined with riding coordinates:
 C2(H2A), C5(H5), C8(H8), C11(H11), C14(H14), C17(H17)
;
_shelx_res_checksum              77384
_shelx_hkl_checksum              29243
_shelx_shelxl_version_number     2014/7
_olex2_date_sample_data_collection 2016-07-04
_olex2_date_sample_submission    2016-07-04
_olex2_exptl_crystal_mounting_method 'mounted on a Mitegen Cryoloop'
_olex2_submission_original_sample_id 'SLB-2-49 in THF/hexane'
_olex2_submission_special_instructions 'No special instructions were received'