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_4034757
_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, C4 H8 O'
_chemical_formula_sum            'C24 H20 O7'
_chemical_formula_weight         420.40
_space_group_crystal_system      orthorhombic
_space_group_IT_number           43
_space_group_name_Hall           'F 2 -2d'
_space_group_name_H-M_alt        'F d d 2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2016-03-24
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            16
_cell_length_a                   21.3113(8)
_cell_length_b                   43.3656(17)
_cell_length_c                   8.4955(3)
_cell_measurement_reflns_used    9967
_cell_measurement_temperature    100
_cell_measurement_theta_max      60.602
_cell_measurement_theta_min      4.023
_cell_volume                     7851.3(5)
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100
_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 0.999
_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  0.0264
_diffrn_reflns_av_unetI/netI     0.0169
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       56
_diffrn_reflns_limit_k_min       -56
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            37484
_diffrn_reflns_point_group_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         60.669
_diffrn_reflns_theta_min         3.547
_diffrn_source                   'Metal Jet'
_diffrn_source_target            Ga
_diffrn_source_type              'Gallium Liquid Metal Jet Source'
_exptl_absorpt_coefficient_mu    0.562
_exptl_absorpt_correction_T_max  0.7519
_exptl_absorpt_correction_T_min  0.6869
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0881 before and 0.0415 after correction.
The Ratio of minimum to maximum transmission is 0.9136.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            'lusterous dark Brown'
_exptl_crystal_colour_lustre     lusterous
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.423
_exptl_crystal_description       platelet
_exptl_crystal_F_000             3520
_exptl_crystal_recrystallization_method 'crystallized in THF/hexane'
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.077
_refine_diff_density_max         0.474
_refine_diff_density_min         -0.291
_refine_diff_density_rms         0.076
_refine_ls_abs_structure_details
;
 Flack x determined using 1800 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.02(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     330
_refine_ls_number_reflns         4359
_refine_ls_number_restraints     155
_refine_ls_restrained_S_all      1.037
_refine_ls_R_factor_all          0.0547
_refine_ls_R_factor_gt           0.0535
_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^)+(0.1034P)^2^+10.1883P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1477
_refine_ls_wR_factor_ref         0.1490
_reflns_Friedel_coverage         0.810
_reflns_Friedel_fraction_full    0.955
_reflns_Friedel_fraction_max     0.927
_reflns_number_gt                4212
_reflns_number_total             4359
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b02706_si_007.cif
_cod_data_source_block           jw18521
_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.

data item '_exptl_crystal_colour_primary' value 'Brown' was changed
to 'brown' 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               4034757
_shelx_estimated_absorpt_t_max   0.958
_shelx_estimated_absorpt_t_min   0.845
_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
C21A \\sim C22A \\sim C23A \\sim C24A \\sim O7A \\sim C21B \\sim C22B \\sim
C23B \\sim C24B \\sim O7B: within 2A with sigma of 0.001 and sigma for terminal
atoms of 0.002
3. Same fragment restrains
{C21A, C22A, C23A, C24A, O7A} sigma for 1-2: 0.02, 1-3: 0.04
as
{C21B, C22B, C23B, C24B, O7B}
4. Others
 Sof(C21B)=Sof(H21C)=Sof(H21D)=Sof(C22B)=Sof(H22C)=Sof(H22D)=Sof(C23B)=
 Sof(H23C)=Sof(H23D)=Sof(C24B)=Sof(H24C)=Sof(H24D)=Sof(O7B)=1-FVAR(1)
 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(O7A)=FVAR(1)
5.a Ternary CH refined with riding coordinates:
 C19(H19), C20(H20)
5.b Secondary CH2 refined with riding coordinates:
 C21A(H21A,H21B), C22A(H22A,H22B), C23A(H23A,H23B), C24A(H24A,H24B), C21B(H21C,
 H21D), C22B(H22C,H22D), C23B(H23C,H23D), C24B(H24C,H24D)
5.c Aromatic/amide H refined with riding coordinates:
 C2(H2A), C5(H5), C9(H9), C12(H12), C15(H15), C18(H18)
5.d Idealised tetrahedral OH refined as rotating group:
 O1(H1), O2(H2), O3(H3), O4(H4)
;
_shelx_res_checksum              64158
_shelx_hkl_checksum              81864
_shelx_shelxl_version_number     2014/7
_olex2_exptl_crystal_mounting_method 'mounted on a Mitegen Microloops'
_olex2_submission_original_sample_id 'SLB-2-49+51 '
_olex2_submission_special_instructions 'No special instructions were received'