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_1570221
_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         'C20 H40 Na O8, C27 H17, 2(C4H8O])'
_chemical_formula_sum            'C55 H73 Na O10'
_chemical_formula_weight         917.12
_space_group_crystal_system      orthorhombic
_space_group_IT_number           52
_space_group_name_Hall           '-P 2a 2bc'
_space_group_name_H-M_alt        'P n n a'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_audit_creation_date             2022-12-12
_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
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.8733(6)
_cell_length_b                   15.5281(6)
_cell_length_c                   19.2855(7)
_cell_measurement_reflns_used    2813
_cell_measurement_temperature    140(2)
_cell_measurement_theta_max      60.67
_cell_measurement_theta_min      3.48
_cell_volume                     5053.0(3)
_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      140(2)
_diffrn_detector_area_resol_mean 10.42
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_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  0.0499
_diffrn_reflns_av_unetI/netI     0.0362
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            16983
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        63.783
_diffrn_reflns_theta_max         63.783
_diffrn_reflns_theta_min         3.654
_diffrn_source                   'microfocus light source'
_diffrn_source_current           1.2
_diffrn_source_power             0.06
_diffrn_source_voltage           50.0
_exptl_absorpt_coefficient_mu    0.726
_exptl_absorpt_correction_T_max  0.7524
_exptl_absorpt_correction_T_min  0.5938
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker, 2016/2) was used for absorption correction.
wR2(int) was 0.1157 before and 0.0677 after correction.
The Ratio of minimum to maximum transmission is 0.7892.
The \l/2 correction factor is not present.
;
_exptl_crystal_colour            red
_exptl_crystal_colour_primary    red
_exptl_crystal_density_diffrn    1.206
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    none
_exptl_crystal_description       block
_exptl_crystal_F_000             1976
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.192
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.033
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     492
_refine_ls_number_reflns         4152
_refine_ls_number_restraints     622
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.1277
_refine_ls_R_factor_gt           0.0738
_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^)+(0.1250P)^2^+0.8964P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2201
_refine_ls_wR_factor_ref         0.2714
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1928
_reflns_number_total             4152
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3sc04885c2.cif
_cod_data_source_block           pnna_a
_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               1570221
_shelx_shelxl_version_number     2019/2
_shelx_estimated_absorpt_t_max   0.965
_shelx_estimated_absorpt_t_min   0.893
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 O1_3-C1_3 \\sim O1-C1
 with sigma of 0.02
 O1_3-C4_3 \\sim O1-C4
 with sigma of 0.02
 C1_3-C2_3 \\sim C1-C2
 with sigma of 0.02
 C2_3-C3_3 \\sim C2-C3
 with sigma of 0.02
 C3_3-C4_3 \\sim C3-C4
 with sigma of 0.02
 O1_3-C2_3 \\sim O1-C2
 with sigma of 0.04
 O1_3-C3_3 \\sim O1-C3
 with sigma of 0.04
 C1_3-C3_3 \\sim C1-C3
 with sigma of 0.04
 C1_3-C4_3 \\sim C1-C4
 with sigma of 0.04
 C2_3-C4_3 \\sim C2-C4
 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
O1_3 \\sim O1 \\sim O3A \\sim O2A \\sim O1_2 \\sim O3_2 \\sim C1_3 \\sim C4_3
\\sim C1 \\sim C4 \\sim C6A \\sim C5A \\sim C4A \\sim C2_2 \\sim C3_2 \\sim
C6_2 \\sim C2_3 \\sim C3_3 \\sim C2 \\sim C3 \\sim C3A \\sim C1_2 \\sim C4_2
\\sim C5_2 \\sim O1A \\sim O2_2 \\sim C2A \\sim C1A \\sim C6_1 \\sim C1_1 \\sim
C2_1 \\sim C9_1 \\sim C3_1 \\sim C5_1 \\sim C7_1 \\sim C8_1 \\sim C13_1 \\sim
C4_1 \\sim C10_1 \\sim C12_1 \\sim C19_1 \\sim C11_1 \\sim C15_1 \\sim C17_1
\\sim C18_1 \\sim C16_1 \\sim C14_1 \\sim C20_1 \\sim C24_1 \\sim C27_1 \\sim
C23_1 \\sim C21_1 \\sim C25_1 \\sim C26_1 \\sim C22_1: within 2A with sigma of
0.01 and sigma for terminal atoms of 0.02 within 2A
4. Same fragment restrains
5. Others
 Sof(O3A)=Sof(C6A)=Sof(H6AA)=Sof(H6AB)=Sof(C5A)=Sof(H5AA)=Sof(H5AB)=Sof(O2A)=
 Sof(C4A)=Sof(H4AA)=Sof(H4AB)=Sof(O1A)=Sof(C3A)=Sof(H3AA)=Sof(H3AB)=Sof(C2A)=
 Sof(H2AA)=Sof(H2AB)=Sof(C1A)=Sof(H1AA)=Sof(H1AB)=1-FVAR(1)
 Sof(O1)=Sof(C1)=Sof(H1A)=Sof(H1B)=Sof(C2)=Sof(H2A)=Sof(H2B)=Sof(C3)=Sof(H3A)=
 Sof(H3B)=Sof(C4)=Sof(H4A)=Sof(H4B)=Sof(C5)=Sof(H5A)=Sof(H5B)=Sof(C6)=Sof(H6A)=
 Sof(H6B)=Sof(O2)=Sof(O3)=FVAR(1)
 Sof(O1)=Sof(C1)=Sof(H1A)=Sof(H1B)=Sof(C2)=Sof(H2A)=Sof(H2B)=Sof(C3)=Sof(H3A)=
 Sof(H3B)=Sof(C4)=Sof(H4A)=Sof(H4B)=1-FVAR(2)
 Sof(O1)=Sof(C1)=Sof(H1A)=Sof(H1B)=Sof(C2)=Sof(H2A)=Sof(H2B)=Sof(C3)=Sof(H3A)=
 Sof(H3B)=Sof(C4)=Sof(H4A)=Sof(H4B)=FVAR(2)
 Fixed Sof: C1(0.5) C2(0.5) H2(0.5) C3(0.5) H3(0.5) C4(0.5) H4(0.5) C5(0.5)
 H5(0.5) C6(0.5) C7(0.5) H7A(0.5) H7B(0.5) C8(0.5) C9(0.5) C10(0.5) C11(0.5)
 C12(0.5) C13(0.5) C16(0.5) H16(0.5) C19(0.5) H19A(0.5) H19B(0.5) C14(0.5)
 C15(0.5) C20(0.5) H20(0.5) C21(0.5) H21(0.5) C22(0.5) H22(0.5) C23(0.5)
 H23(0.5) C18(0.5) C27(0.5) H27(0.5) C26(0.5) H26(0.5) C25(0.5) H25(0.5)
 C24(0.5) H24(0.5) C17(0.5)
6.a Secondary CH2 refined with riding coordinates:
 C6A(H6AA,H6AB), C5A(H5AA,H5AB), C4A(H4AA,H4AB), C3A(H3AA,H3AB), C2A(H2AA,
 H2AB), C1A(H1AA,H1AB), C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B),
 C7(H7A,H7B), C19(H19A,H19B), C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B), C4(H4A,
 H4B), C5(H5A,H5B), C6(H6A,H6B), C1(H1A,H1B), C2(H2A,H2B), C3(H3A,H3B), C4(H4A,
 H4B)
6.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C16(H16), C20(H20), C21(H21), C22(H22),
 C23(H23), C27(H27), C26(H26), C25(H25), C24(H24)
6.c Fitted hexagon refined as free rotating group:
 C18(C27,C26,C25,C24,C17)
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              50766
_shelx_hkl_checksum              18709
_shelx_fab_checksum              99726
_olex2_submission_special_instructions 'No special instructions were received'