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_4034755
_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 H12 O6, 3.5(C4 H8 O2)'
_chemical_formula_sum            'C34 H40 O13'
_chemical_formula_weight         656.66
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-I 2ya'
_space_group_name_H-M_alt        'I 1 2/a 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-05-04
_audit_creation_method
;
Olex2 1.2
(compiled 2018.04.26 svn.r3504 for OlexSys, GUI svn.r5492)
;
_cell_angle_alpha                90
_cell_angle_beta                 93.151(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   24.0009(11)
_cell_length_b                   8.5212(4)
_cell_length_c                   31.560(2)
_cell_measurement_reflns_used    9881
_cell_measurement_temperature    150
_cell_measurement_theta_max      51.719
_cell_measurement_theta_min      2.441
_cell_volume                     6444.8(6)
_computing_cell_refinement
'SAINT (2013) V8.38A; 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) V8.38A; 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      150
_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 0.996
_diffrn_measured_fraction_theta_max 0.996
_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  0.0764
_diffrn_reflns_av_unetI/netI     0.0482
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            40908
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        52.320
_diffrn_reflns_theta_max         52.320
_diffrn_reflns_theta_min         2.440
_diffrn_source                   'Metal Jet'
_diffrn_source_target            Ga
_diffrn_source_type              'Gallium Liquid Metal Jet Source'
_exptl_absorpt_coefficient_mu    0.560
_exptl_absorpt_correction_T_max  0.7503
_exptl_absorpt_correction_T_min  0.6135
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1330 before and 0.0798 after correction. The Ratio of minimum to maximum transmission is 0.8177. The \l/2 correction factor is Not present.'
_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    1.354
_exptl_crystal_description       Platelet
_exptl_crystal_F_000             2784
_exptl_crystal_recrystallization_method 'crystallized from Dioxane/hexane'
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.03
_refine_diff_density_max         0.531
_refine_diff_density_min         -0.360
_refine_diff_density_rms         0.065
_refine_ls_extinction_coef       0.00031(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     476
_refine_ls_number_reflns         5526
_refine_ls_number_restraints     250
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.1295
_refine_ls_R_factor_gt           0.0811
_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^)+(0.1414P)^2^+9.8338P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2113
_refine_ls_wR_factor_ref         0.2532
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3431
_reflns_number_total             5526
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b02706_si_005.cif
_cod_data_source_block           jw2050
_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               4034755
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.983
_shelx_estimated_absorpt_t_min   0.911
_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. Restrained distances
 C21A-C22A = C21B-C22B = C23A-C24A = C23B-C24B
 1.5 with sigma of 0.001
 O13A-C33A \\sim O13A-C34A \\sim O13B-C33B \\sim O13B-C34B
 with sigma of 0.02
 O7A-C21A \\sim O7B-C21B \\sim O7A-C24A \\sim O7B-C24B
 with sigma of 0.02
 O8A-C22A \\sim O8B-C22B \\sim O8A-C23A \\sim O8B-C23B
 with sigma of 0.02
 C21A-C22A \\sim C21B-C22B \\sim C23A-C24A \\sim C23B-C24B
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
O13A \\sim O13B \\sim C33A \\sim C33B \\sim C34A \\sim C34B: within 2A with
sigma of 0.02 and sigma for terminal atoms of 0.01
O7A \\sim C21A \\sim C22A \\sim C23A \\sim C24A \\sim O8A \\sim O7B \\sim C21B
\\sim C22B \\sim C23B \\sim C24B \\sim O8B: within 2A with sigma of 0.02 and
sigma for terminal atoms of 0.01
Uanis(C21A) = Uanis(C21B)
Uanis(C22A) = Uanis(C22B)
Uanis(C23A) = Uanis(C23B)
Uanis(C24A) = Uanis(C24B)
Uanis(O7A) = Uanis(O7B)
Uanis(O8A) = Uanis(O8B)
4. Others
 Sof(O13B)=Sof(C33B)=Sof(H33C)=Sof(H33D)=Sof(C34B)=Sof(H34C)=Sof(H34D)=1-FVAR(1)
 Sof(C34A)=Sof(H34A)=Sof(H34B)=Sof(C33A)=Sof(H33A)=Sof(H33B)=Sof(O13A)=FVAR(1)
 Sof(O7B)=Sof(C23B)=Sof(H23C)=Sof(H23D)=Sof(C24B)=Sof(H24C)=Sof(H24D)=
 Sof(C21B)=Sof(H21C)=Sof(H21D)=Sof(C22B)=Sof(H22C)=Sof(H22D)=Sof(O8B)=1-FVAR(2)
 Sof(O7A)=Sof(C21A)=Sof(H21A)=Sof(H21B)=Sof(C22A)=Sof(H22A)=Sof(H22B)=
 Sof(C23A)=Sof(H23A)=Sof(H23B)=Sof(C24A)=Sof(H24A)=Sof(H24B)=Sof(O8A)=FVAR(2)
5.a Ternary CH refined with riding coordinates:
 C19(H19), C20(H20)
5.b Secondary CH2 refined with riding coordinates:
 C29(H29A,H29B), C30(H30A,H30B), C31(H31A,H31B), C32(H32A,H32B), C25(H25A,
 H25B), C26(H26A,H26B), C27(H27A,H27B), C28(H28A,H28B), C34A(H34A,H34B),
 C33A(H33A,H33B), C33B(H33C,H33D), C34B(H34C,H34D), C21A(H21A,H21B), C22A(H22A,
 H22B), C23A(H23A,H23B), C24A(H24A,H24B), C23B(H23C,H23D), C24B(H24C,H24D),
 C21B(H21C,H21D), C22B(H22C,H22D)
5.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5A), C9(H9), C12(H12), C15(H15), C18(H18)
5.d Idealised tetrahedral OH refined as rotating group:
 O3(H3), O4(H4), O5(H5), O6(H6)
;
_shelx_res_checksum              95762
_shelx_hkl_checksum              15380
_olex2_date_sample_data_collection 2018-05-02
_olex2_date_sample_submission    2018-05-01
_olex2_exptl_crystal_mounting_method 'mouted on a cryoloop'
_olex2_submission_original_sample_id 'SLB-2-51 '
_olex2_submission_special_instructions 'No special instructions were received'