Stepwise deprotonation of truxene: structures, metal complexation, and charge-dependent optical properties.
Guo, Yumeng; Torchon, Herdya S.; Zhu, Yikun; Wei, Zheng; Zhang, Zhenyi; Han, Haixiang; Petrukhina, Marina A.; Zhou, Zheng; Chemical science 14 (2023) 13219–13227; doi:10.1039/d3sc04885c

data_1570220
_publ_section_title
;
 Stepwise deprotonation of truxene: structures, metal complexation, and
 charge-dependent optical properties.
;
_journal_issue                   45
_journal_name_full               'Chemical science'
_journal_page_first              13219
_journal_page_last               13227
_journal_paper_doi               10.1039/d3sc04885c
_journal_volume                  14
_journal_year                    2023
_chemical_formula_moiety         'C27 H18'
_chemical_formula_sum            'C27 H18'
_chemical_formula_weight         342.41
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2022-11-30
_audit_creation_method
;
Olex2 1.5-alpha
(compiled 2022.11.02 svn.ra8b101fa for OlexSys, GUI svn.r6635)
;
_audit_update_record
;
2023-08-18 deposited with the CCDC.	2023-10-31 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90.473(2)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   4.68560(10)
_cell_length_b                   16.2628(5)
_cell_length_c                   11.3085(4)
_cell_measurement_reflns_used    3675
_cell_measurement_temperature    157(2)
_cell_measurement_theta_max      77.97
_cell_measurement_theta_min      9.56
_cell_volume                     861.69(4)
_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 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      157(2)
_diffrn_detector_area_resol_mean 10.42
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.923
_diffrn_measurement_device_type  'Bruker D8 Venture PHOTON 100 CMOS'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0305
_diffrn_reflns_av_unetI/netI     0.0302
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.923
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7043
_diffrn_reflns_point_group_measured_fraction_full 0.935
_diffrn_reflns_point_group_measured_fraction_max 0.844
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         79.599
_diffrn_reflns_theta_min         9.470
_diffrn_source                   'micro focus light source'
_diffrn_source_current           1.11
_diffrn_source_power             0.05550000000000001
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.566
_exptl_absorpt_correction_T_max  0.9562
_exptl_absorpt_correction_T_min  0.8214
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker, 2016/2) was used for absorption correction.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.320
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    none
_exptl_crystal_description       block
_exptl_crystal_F_000             360
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.170
_refine_diff_density_min         -0.103
_refine_diff_density_rms         0.026
_refine_ls_abs_structure_details
;
 Flack x determined using 1163 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.7(9)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     488
_refine_ls_number_reflns         3143
_refine_ls_number_restraints     1159
_refine_ls_restrained_S_all      0.972
_refine_ls_R_factor_all          0.0439
_refine_ls_R_factor_gt           0.0405
_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^)+(0.0610P)^2^+0.0762P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1050
_refine_ls_wR_factor_ref         0.1076
_reflns_Friedel_coverage         0.767
_reflns_Friedel_fraction_full    0.879
_reflns_Friedel_fraction_max     0.760
_reflns_number_gt                2899
_reflns_number_total             3143
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc04885c2.cif
_cod_data_source_block           1
_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 1570220--1570225.cif.
;
_cod_database_code               1570220
_shelx_shelxl_version_number     2019/2
_shelx_estimated_absorpt_t_max   0.967
_shelx_estimated_absorpt_t_min   0.935
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 C9-C8 \\sim C27X-C26X
 with sigma of 0.02
 C9-C10 \\sim C27X-C1X
 with sigma of 0.02
 C9-C1 \\sim C27X-C19X
 with sigma of 0.02
 C8-C3 \\sim C26X-C21X
 with sigma of 0.02
 C8-C7 \\sim C26X-C25X
 with sigma of 0.02
 C10-C18 \\sim C1X-C9X
 with sigma of 0.02
 C10-C11 \\sim C1X-C2X
 with sigma of 0.02
 C15-C16 \\sim C6X-C7X
 with sigma of 0.02
 C15-C14 \\sim C6X-C5X
 with sigma of 0.02
 C24-C23 \\sim C15X-C14X
 with sigma of 0.02
 C24-C25 \\sim C15X-C16X
 with sigma of 0.02
 C5-C4 \\sim C23X-C22X
 with sigma of 0.02
 C5-C6 \\sim C23X-C24X
 with sigma of 0.02
 C27-C1 \\sim C18X-C19X
 with sigma of 0.02
 C27-C26 \\sim C18X-C17X
 with sigma of 0.02
 C27-C19 \\sim C18X-C10X
 with sigma of 0.02
 C1-C2 \\sim C19X-C20X
 with sigma of 0.02
 C26-C21 \\sim C17X-C12X
 with sigma of 0.02
 C26-C25 \\sim C17X-C16X
 with sigma of 0.02
 C23-C22 \\sim C14X-C13X
 with sigma of 0.02
 C4-C3 \\sim C22X-C21X
 with sigma of 0.02
 C3-C2 \\sim C21X-C20X
 with sigma of 0.02
 C18-C17 \\sim C9X-C8X
 with sigma of 0.02
 C18-C19 \\sim C9X-C10X
 with sigma of 0.02
 C16-C17 \\sim C7X-C8X
 with sigma of 0.02
 C17-C12 \\sim C8X-C3X
 with sigma of 0.02
 C19-C20 \\sim C10X-C11X
 with sigma of 0.02
 C14-C13 \\sim C5X-C4X
 with sigma of 0.02
 C21-C22 \\sim C12X-C13X
 with sigma of 0.02
 C21-C20 \\sim C12X-C11X
 with sigma of 0.02
 C7-C6 \\sim C25X-C24X
 with sigma of 0.02
 C12-C13 \\sim C3X-C4X
 with sigma of 0.02
 C12-C11 \\sim C3X-C2X
 with sigma of 0.02
 C9-C27 \\sim C27X-C18X
 with sigma of 0.04
 C9-C3 \\sim C27X-C21X
 with sigma of 0.04
 C9-C18 \\sim C27X-C9X
 with sigma of 0.04
 C9-C7 \\sim C27X-C25X
 with sigma of 0.04
 C9-C11 \\sim C27X-C2X
 with sigma of 0.04
 C9-C2 \\sim C27X-C20X
 with sigma of 0.04
 C8-C10 \\sim C26X-C1X
 with sigma of 0.04
 C8-C1 \\sim C26X-C19X
 with sigma of 0.04
 C8-C4 \\sim C26X-C22X
 with sigma of 0.04
 C8-C6 \\sim C26X-C24X
 with sigma of 0.04
 C8-C2 \\sim C26X-C20X
 with sigma of 0.04
 C10-C1 \\sim C1X-C19X
 with sigma of 0.04
 C10-C17 \\sim C1X-C8X
 with sigma of 0.04
 C10-C19 \\sim C1X-C10X
 with sigma of 0.04
 C10-C12 \\sim C1X-C3X
 with sigma of 0.04
 C15-C17 \\sim C6X-C8X
 with sigma of 0.04
 C15-C13 \\sim C6X-C4X
 with sigma of 0.04
 C24-C26 \\sim C15X-C17X
 with sigma of 0.04
 C24-C22 \\sim C15X-C13X
 with sigma of 0.04
 C5-C3 \\sim C23X-C21X
 with sigma of 0.04
 C5-C7 \\sim C23X-C25X
 with sigma of 0.04
 C27-C18 \\sim C18X-C9X
 with sigma of 0.04
 C27-C21 \\sim C18X-C12X
 with sigma of 0.04
 C27-C25 \\sim C18X-C16X
 with sigma of 0.04
 C27-C20 \\sim C18X-C11X
 with sigma of 0.04
 C27-C2 \\sim C18X-C20X
 with sigma of 0.04
 C1-C26 \\sim C19X-C17X
 with sigma of 0.04
 C1-C3 \\sim C19X-C21X
 with sigma of 0.04
 C1-C19 \\sim C19X-C10X
 with sigma of 0.04
 C26-C19 \\sim C17X-C10X
 with sigma of 0.04
 C26-C22 \\sim C17X-C13X
 with sigma of 0.04
 C26-C20 \\sim C17X-C11X
 with sigma of 0.04
 C23-C21 \\sim C14X-C12X
 with sigma of 0.04
 C23-C25 \\sim C14X-C16X
 with sigma of 0.04
 C4-C6 \\sim C22X-C24X
 with sigma of 0.04
 C4-C2 \\sim C22X-C20X
 with sigma of 0.04
 C3-C7 \\sim C21X-C25X
 with sigma of 0.04
 C18-C16 \\sim C9X-C7X
 with sigma of 0.04
 C18-C12 \\sim C9X-C3X
 with sigma of 0.04
 C18-C20 \\sim C9X-C11X
 with sigma of 0.04
 C18-C11 \\sim C9X-C2X
 with sigma of 0.04
 C16-C14 \\sim C7X-C5X
 with sigma of 0.04
 C16-C12 \\sim C7X-C3X
 with sigma of 0.04
 C17-C19 \\sim C8X-C10X
 with sigma of 0.04
 C17-C13 \\sim C8X-C4X
 with sigma of 0.04
 C17-C11 \\sim C8X-C2X
 with sigma of 0.04
 C19-C21 \\sim C10X-C12X
 with sigma of 0.04
 C14-C12 \\sim C5X-C3X
 with sigma of 0.04
 C21-C25 \\sim C12X-C16X
 with sigma of 0.04
 C22-C20 \\sim C13X-C11X
 with sigma of 0.04
 C13-C11 \\sim C4X-C2X
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
C11X \\sim C25 \\sim C2 \\sim C7X \\sim C18X \\sim C14X \\sim C25X \\sim C5X
\\sim C11 \\sim C4X \\sim C22X \\sim C6X \\sim C23X \\sim C13X \\sim C12 \\sim
C12X \\sim C26X \\sim C15X \\sim C9X \\sim C16X \\sim C27X \\sim C24 \\sim C8X
\\sim C16 \\sim C3X \\sim C10 \\sim C21X \\sim C15 \\sim C7 \\sim C9 \\sim C19
\\sim C1 \\sim C20 \\sim C26 \\sim C13 \\sim C23 \\sim C1X \\sim C4 \\sim C19X
\\sim C18 \\sim C22 \\sim C8 \\sim C20X \\sim C27 \\sim C24X \\sim C3 \\sim C6
\\sim C5 \\sim C10X \\sim C17 \\sim C17X \\sim C21 \\sim C2X \\sim C14: within
2A with sigma of 0.01 and sigma for terminal atoms of 0.02 within 2A
4. Others
 Sof(C2X)=Sof(H2XA)=Sof(H2XB)=Sof(C27X)=Sof(C26X)=Sof(C1X)=Sof(C19X)=Sof(C21X)=
 Sof(C25X)=Sof(H25X)=Sof(C9X)=Sof(C18X)=Sof(C20X)=Sof(H20C)=Sof(H20D)=Sof(C22X)=
 Sof(H22X)=Sof(C24X)=Sof(H24X)=Sof(C8X)=Sof(C10X)=Sof(C3X)=Sof(C17X)=Sof(C23X)=
 Sof(H23X)=Sof(C7X)=Sof(H7X)=Sof(C11X)=Sof(H11C)=Sof(H11D)=Sof(C4X)=Sof(H4X)=
 Sof(C12X)=Sof(C16X)=Sof(H16X)=Sof(C6X)=Sof(H6X)=Sof(C5X)=Sof(H5X)=Sof(C13X)=
 Sof(H13X)=Sof(C15X)=Sof(H15X)=Sof(C14X)=Sof(H14X)=1-FVAR(1)
 Sof(C9)=Sof(C8)=Sof(C10)=Sof(C15)=Sof(H15)=Sof(C24)=Sof(H24)=Sof(C5)=Sof(H5)=
 Sof(C27)=Sof(C1)=Sof(C26)=Sof(C23)=Sof(H23)=Sof(C4)=Sof(H4)=Sof(C3)=Sof(C18)=
 Sof(C16)=Sof(H16)=Sof(C17)=Sof(C19)=Sof(C14)=Sof(H14)=Sof(C21)=Sof(C7)=Sof(H7)=
 Sof(C6)=Sof(H6)=Sof(C25)=Sof(H25)=Sof(C22)=Sof(H22)=Sof(C12)=Sof(C13)=Sof(H13)=
 Sof(C20)=Sof(H20A)=Sof(H20B)=Sof(C11)=Sof(H11A)=Sof(H11B)=Sof(C2)=Sof(H2A)=
 Sof(H2B)=FVAR(1)
5.a Secondary CH2 refined with riding coordinates:
 C20(H20A,H20B), C11(H11A,H11B), C2(H2A,H2B), C2X(H2XA,H2XB), C20X(H20C,H20D),
 C11X(H11C,H11D)
5.b Aromatic/amide H refined with riding coordinates:
 C15(H15), C24(H24), C5(H5), C23(H23), C4(H4), C16(H16), C14(H14), C7(H7),
 C6(H6), C25(H25), C22(H22), C13(H13), C25X(H25X), C22X(H22X), C24X(H24X),
 C23X(H23X), C7X(H7X), C4X(H4X), C16X(H16X), C6X(H6X), C5X(H5X), C13X(H13X),
 C15X(H15X), C14X(H14X)
;
_shelx_res_checksum              46760
_shelx_hkl_checksum              58946
_olex2_submission_special_instructions 'No special instructions were received'