Chemical reduction of π-expanded functionalized pentacene: cooperation of side group in alkali metal binding.
Pennachio, Matthew; Wei, Zheng; Mamada, Masashi; Frigoli, Michel; Petrukhina, Marina A.; Chemical communications (Cambridge, England) 60 (2024) 9526–9529; doi:10.1039/d4cc03318c

data_7133514
_publ_section_title
;
 Chemical reduction of &#x3c0;-expanded functionalized pentacene:
 cooperation of side group in alkali metal binding.
;
_journal_issue                   71
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              9526
_journal_page_last               9529
_journal_paper_doi               10.1039/d4cc03318c
_journal_volume                  60
_journal_year                    2024
_chemical_formula_moiety         'C80 H104 Na2 O6 Si2'
_chemical_formula_sum            'C80 H104 Na2 O6 Si2'
_chemical_formula_weight         1263.79
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2022-04-20
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2024-07-02 deposited with the CCDC.	2024-08-08 downloaded from the CCDC.
;
_cell_angle_alpha                97.3160(10)
_cell_angle_beta                 100.1920(10)
_cell_angle_gamma                100.4480(10)
_cell_formula_units_Z            1
_cell_length_a                   7.7756(2)
_cell_length_b                   14.1848(4)
_cell_length_c                   16.3912(5)
_cell_measurement_reflns_used    9783
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      22.13
_cell_measurement_theta_min      2.45
_cell_volume                     1725.94(9)
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2018)'
_computing_data_collection       'APEX3 v.2018.7-2 (Bruker AXS Inc., 2018)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2018)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Pilatus1M(CdTe) pixel array detector'
_diffrn_detector_area_resol_mean 30
_diffrn_detector_type            'CMOS pixel array detector'
_diffrn_measured_fraction_theta_full 0.960
_diffrn_measured_fraction_theta_max 0.930
_diffrn_measurement_device_type  'APS_15-ID-D xHuber Kappa'
_diffrn_measurement_method       'phi rotation'
_diffrn_radiation_collimation    '0.2 mm sinlge-pinhole'
_diffrn_radiation_monochromator  'Si(111) & Si(311)'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           synchrotron
_diffrn_radiation_wavelength     0.41328
_diffrn_reflns_av_R_equivalents  0.0430
_diffrn_reflns_av_unetI/netI     0.0321
_diffrn_reflns_Laue_measured_fraction_full 0.960
_diffrn_reflns_Laue_measured_fraction_max 0.930
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            115112
_diffrn_reflns_point_group_measured_fraction_full 0.960
_diffrn_reflns_point_group_measured_fraction_max 0.930
_diffrn_reflns_theta_full        14.357
_diffrn_reflns_theta_max         22.173
_diffrn_reflns_theta_min         1.041
_diffrn_source                   synchrotron
_diffrn_source_current           103.0
_diffrn_source_power             103.0
_diffrn_source_type
'Insertion Device, Station 15 ID-B, APS, Argonne Nat'l Lab'
_diffrn_source_voltage           1000.0
_exptl_absorpt_coefficient_mu    0.042
_exptl_absorpt_correction_T_max  0.7447
_exptl_absorpt_correction_T_min  0.5886
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker, 2016/2) was used for absorption correction.
wR2(int) was 0.0854 before and 0.0528 after correction.
The Ratio of minimum to maximum transmission is 0.7904.
The \l/2 correction factor is not present.
;
_exptl_crystal_colour            'dark red'
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.216
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    none
_exptl_crystal_description       block
_exptl_crystal_F_000             682
_exptl_crystal_size_max          0.013
_exptl_crystal_size_mid          0.009
_exptl_crystal_size_min          0.008
_refine_diff_density_max         0.657
_refine_diff_density_min         -0.561
_refine_diff_density_rms         0.053
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     436
_refine_ls_number_reflns         20479
_refine_ls_number_restraints     102
_refine_ls_restrained_S_all      1.092
_refine_ls_R_factor_all          0.0567
_refine_ls_R_factor_gt           0.0433
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0747P)^2^+0.1346P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1318
_refine_ls_wR_factor_ref         0.1399
_reflns_Friedel_coverage         0.000
_reflns_number_gt                15721
_reflns_number_total             20479
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d4cc03318c2.cif
_cod_data_source_block           Na2_TIPS_PPP
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_crystal_density_meas' value 'not measured' was
changed to '?' -- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 8170 2020-07-09 18:12:32Z antanas 

 Adding full bibliography for 7133514.cif.
;
_cod_original_cell_volume        1725.94(8)
_cod_database_code               7133514
_shelx_shelxl_version_number     2019/2
_shelx_estimated_absorpt_t_max   1.000
_shelx_estimated_absorpt_t_min   0.999
_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 C(H,H,H) groups
2. Restrained distances
 Si1-C23 \\sim Si1-C23X
 with sigma of 0.02
 C23-C24 \\sim C23X-C25X
 with sigma of 0.02
 C23-C25 \\sim C23X-C24X
 with sigma of 0.02
 C24-C25 \\sim C25X-C24X
 with sigma of 0.04
 Si1-C24 \\sim Si1-C25X
 with sigma of 0.04
 Si1-C25 \\sim Si1-C24X
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
C23 \\sim C24 \\sim C25 \\sim C23X \\sim C24X \\sim C25X: within 2A with sigma
of 0.01 and sigma for terminal atoms of 0.02 within 2A
Uanis(C23X) = Uanis(C23)
4. Rigid body (RIGU) restrains
 Si1, C23, C24, C25, C23X, C24X, C25X
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(C23X)=Sof(H23X)=Sof(C24X)=Sof(H24D)=Sof(H24E)=Sof(H24F)=Sof(C25X)=
 Sof(H25D)=Sof(H25E)=Sof(H25F)=1-FVAR(1)
 Sof(C23)=Sof(H23)=Sof(C24)=Sof(H24A)=Sof(H24B)=Sof(H24C)=Sof(C25)=Sof(H25A)=
 Sof(H25B)=Sof(H25C)=FVAR(1)
6.a Ternary CH refined with riding coordinates:
 C20(H20), C23(H23), C26(H26), C23X(H23X)
6.b Secondary CH2 refined with riding coordinates:
 C29(H29A,H29B), C30(H30A,H30B), C31(H31A,H31B), C32(H32A,H32B), C33(H33A,
 H33B), C34(H34A,H34B), C35(H35A,H35B), C36(H36A,H36B), C37(H37A,H37B),
 C38(H38A,H38B), C39(H39A,H39B), C40(H40A,H40B)
6.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5), C6(H6), C8(H8), C9(H9), C10(H10), C12(H12)
6.d Idealised Me refined as rotating group:
 C21(H21A,H21B,H21C), C22(H22A,H22B,H22C), C24(H24A,H24B,H24C), C25(H25A,H25B,
 H25C), C27(H27A,H27B,H27C), C28(H28A,H28B,H28C), C24X(H24D,H24E,H24F),
 C25X(H25D,H25E,H25F)
;
_shelx_res_checksum              51616
_shelx_hkl_checksum              17561
_olex2_submission_special_instructions 'No special instructions were received'