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_4034756
_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_absolute_configuration ad
_chemical_formula_moiety         'C20 H8 O6, 1(C2 H3 N)'
_chemical_formula_sum            'C22 H11 N O6'
_chemical_formula_weight         385.32
_space_group_crystal_system      hexagonal
_space_group_IT_number           173
_space_group_name_Hall           'P 6c'
_space_group_name_H-M_alt        'P 63'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2017-11-08
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            6
_cell_length_a                   15.7405(3)
_cell_length_b                   15.7405(3)
_cell_length_c                   11.9054(3)
_cell_measurement_reflns_used    9878
_cell_measurement_temperature    150
_cell_measurement_theta_max      60.511
_cell_measurement_theta_min      3.231
_cell_volume                     2554.53(9)
_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 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  0.0415
_diffrn_reflns_av_unetI/netI     0.0246
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            38684
_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         60.512
_diffrn_reflns_theta_min         2.820
_diffrn_source                   'Metal Jet'
_diffrn_source_target            Ga
_diffrn_source_type              'Gallium Liquid Metal Jet Source'
_exptl_absorpt_coefficient_mu    0.599
_exptl_absorpt_correction_T_max  0.7519
_exptl_absorpt_correction_T_min  0.6275
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1316 before and 0.0681 after correction. The Ratio of minimum to maximum transmission is 0.8346. 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    1.503
_exptl_crystal_description       needle
_exptl_crystal_F_000             1188
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.1
_refine_diff_density_max         1.169
_refine_diff_density_min         -0.787
_refine_diff_density_rms         0.188
_refine_ls_abs_structure_details
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.3(5)
_refine_ls_extinction_coef       0.018(3)
_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   1.252
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     282
_refine_ls_number_reflns         3924
_refine_ls_number_restraints     39
_refine_ls_restrained_S_all      1.284
_refine_ls_R_factor_all          0.1035
_refine_ls_R_factor_gt           0.0968
_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^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2556
_refine_ls_wR_factor_ref         0.2804
_reflns_Friedel_coverage         0.907
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                3184
_reflns_number_total             3924
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b02706_si_002.cif
_cod_data_source_block           jw2000
_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_original_cell_volume        2554.53(12)
_cod_database_code               4034756
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.943
_shelx_estimated_absorpt_t_min   0.841
_olex2_refinement_description
;
1. Twinned data refinement
 Scales: 0.7(5)
 0.3(5)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
3. Restrained distances
 N1A-C1A = N1B_$1-C1B_$1 = N1C_$2-C1C_$2 = N1D_$2-C1D_$2 = N1E_$1-C1E_$1 = N1F-
 C1F
 1.18 with sigma of 0.002
 C1A-C2A = C1B_$1-C2B_$1 = C1C_$2-C2C_$2 = C1D_$2-C2D_$2 = C1E_$1-C2E_$1 = C1F-
 C2F
 1.53 with sigma of 0.002
4. Rigid bond restraints
 N1C, C1C, C2C, N1D, C1D, C2D, N1A, C1A, C2A, N1E, C1E, C2E, N1B, C1B, C2B,
 N1F, C1F, C2F
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
5. Uiso/Uaniso restraints and constraints
N1C \\sim C1C \\sim C2C \\sim N1D \\sim C1D \\sim C2D \\sim N1A \\sim C1A \\sim
C2A \\sim N1E \\sim C1E \\sim C2E \\sim N1B \\sim C1B \\sim C2B \\sim N1F \\sim
C1F \\sim C2F: within 2A with sigma of 0.002 and sigma for terminal atoms of
0.02
6. Same fragment restrains
{N1C, C1C, C2C} sigma for 1-2: 0.02, 1-3: 0.04
as
{N1D, C1D, C2D}
{N1A, C1A, C2A} sigma for 1-2: 0.02, 1-3: 0.04
as
{N1E, C1E, C2E}
{N1B, C1B, C2B} sigma for 1-2: 0.02, 1-3: 0.04
as
{N1F, C1F, C2F}
7. Others
 Sof(N1D)=Sof(C1D)=Sof(C2D)=Sof(H2DC)=Sof(H2DA)=Sof(H2DB)=0.33333*(1-FVAR(2))
 Sof(N1C)=Sof(C1C)=Sof(C2C)=Sof(H2CC)=Sof(H2CB)=Sof(H2CA)=0.33333*FVAR(2)
 Sof(N1E)=Sof(C1E)=Sof(C2E)=Sof(H2EA)=Sof(H2EB)=Sof(H2EC)=0.33333*(1-FVAR(3))
 Sof(N1A)=Sof(C1A)=Sof(C2A)=Sof(H2AA)=Sof(H2AB)=Sof(H2AC)=0.33333*FVAR(3)
 Sof(N1F)=Sof(C1F)=Sof(C2F)=Sof(H2FA)=Sof(H2FB)=Sof(H2FC)=0.33333*(1-FVAR(4))
 Sof(N1B)=Sof(C1B)=Sof(C2B)=Sof(H2BC)=Sof(H2BA)=Sof(H2BB)=0.33333*FVAR(4)
8.a Ternary CH refined with riding coordinates:
 C1(H1), C8(H8)
8.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C6(H6), C10(H10), C13(H13), C16(H16), C19(H19)
8.c Idealised Me refined as rotating group:
 C2C(H2CC,H2CB,H2CA), C2D(H2DC,H2DA,H2DB), C2A(H2AA,H2AB,H2AC), C2E(H2EA,H2EB,
 H2EC), C2B(H2BC,H2BA,H2BB), C2F(H2FA,H2FB,H2FC)
;
_shelx_res_checksum              51902
_shelx_hkl_checksum              78788
_olex2_date_sample_data_collection 2017-11-03
_olex2_date_sample_submission    2017-11-03
_olex2_submission_original_sample_id 'SLB- '
_olex2_submission_special_instructions 'No special instructions were received'