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_4034758
_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, 3(C2 H4 O)'
_chemical_formula_sum            'C26 H22 O9'
_chemical_formula_weight         478.43
_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   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-11-15
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                90
_cell_angle_beta                 109.286(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   17.2624(5)
_cell_length_b                   8.6308(2)
_cell_length_c                   16.1531(5)
_cell_measurement_reflns_used    9653
_cell_measurement_temperature    150
_cell_measurement_theta_max      54.999
_cell_measurement_theta_min      2.360
_cell_volume                     2271.57(11)
_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    'ShelXT (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 0.999
_diffrn_measured_fraction_theta_max 0.995
_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  0.0405
_diffrn_reflns_av_unetI/netI     0.0247
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            29785
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         55.085
_diffrn_reflns_theta_min         2.359
_diffrn_source                   'Metal Jet'
_diffrn_source_target            Ga
_diffrn_source_type              'Gallium Liquid Metal Jet Source'
_exptl_absorpt_coefficient_mu    0.574
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.6605
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1190 before and 0.0631 after correction. The Ratio of minimum to maximum transmission is 0.8797. 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    1.399
_exptl_crystal_description       plate
_exptl_crystal_F_000             1000
_exptl_crystal_recrystallization_method 'crystallized from Dioxane/PhMe'
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.622
_refine_diff_density_min         -0.446
_refine_diff_density_rms         0.055
_refine_ls_extinction_coef       0.0056(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     374
_refine_ls_number_reflns         4327
_refine_ls_number_restraints     214
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0654
_refine_ls_R_factor_gt           0.0539
_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^)+(0.0604P)^2^+2.3480P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1298
_refine_ls_wR_factor_ref         0.1397
_reflns_Friedel_coverage         0.000
_reflns_number_gt                3615
_reflns_number_total             4327
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b02706_si_003.cif
_cod_data_source_block           jw2003
_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               4034758
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.977
_shelx_estimated_absorpt_t_min   0.889
_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
 O1B-C1B \\sim O1B-C4B \\sim O2B-C2B \\sim O2B-C3B \\sim O1C-C1C \\sim O1C-C4C
\\sim O2C-C3C \\sim O2C-C2C
 with sigma of 0.001
 C1B-C2B \\sim C3B-C4B \\sim C1C-C2C \\sim C3C-C4C
 with sigma of 0.001
3. Uiso/Uaniso restraints and constraints
O1B \\sim C1B \\sim C2B \\sim C3B \\sim C4B \\sim O2B \\sim O1C \\sim C1C \\sim
C2C \\sim C3C \\sim C4C \\sim O2C: within 2A with sigma of 0.002 and sigma for
terminal atoms of 0.004
4. Others
 Sof(O1C)=Sof(C1C)=Sof(H1CA)=Sof(H1CB)=Sof(C2C)=Sof(H2CA)=Sof(H2CB)=Sof(C3C)=
 Sof(H3CA)=Sof(H3CB)=Sof(C4C)=Sof(H4CA)=Sof(H4CB)=Sof(O2C)=1-FVAR(1)
 Sof(O1B)=Sof(O2B)=Sof(C1B)=Sof(H1BA)=Sof(H1BB)=Sof(C2B)=Sof(H2BA)=Sof(H2BB)=
 Sof(C3B)=Sof(H3BA)=Sof(H3BB)=Sof(C4B)=Sof(H4BA)=Sof(H4BB)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C19(H19), C20(H20)
5.b Secondary CH2 refined with riding coordinates:
 C1A(H1AA,H1AB), C2A(H2AA,H2AB), C1B(H1BA,H1BB), C2B(H2BA,H2BB), C3B(H3BA,
 H3BB), C4B(H4BA,H4BB), C1C(H1CA,H1CB), C2C(H2CA,H2CB), C3C(H3CA,H3CB),
 C4C(H4CA,H4CB)
5.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5), C8(H8), C11(H11), C15(H15), C18(H18)
5.d Idealised tetrahedral OH refined as rotating group:
 O1(H1), O2(H2A)
;
_shelx_res_checksum              73352
_shelx_hkl_checksum              85551
_olex2_date_sample_data_collection 2017-11-14
_olex2_date_sample_submission    2017-11-14
_olex2_exptl_crystal_mounting_method 'mounted on a cryoloop'
_olex2_submission_original_sample_id 'SLB-2-49 Dioxane/PhMe'
_olex2_submission_special_instructions 'No special instructions were received'