Macrocyclic Geminal Diols: Synthesis, Structures, Stability and Photophysical Properties
Zou, Bo; Chen, Xiaolin; Liu, Haoran; Wen, Sijie; Huang, Jieqing; Wei, Hengshan; Huang, Jinqing; Gu, Yu-Cheng; Xu, Bingjia; Fan, Jun; Jiang, Hua-Wei; Chemical Science  (2025) –; doi:10.1039/D5SC08216A

data_1576260
_publ_section_title
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 Macrocyclic Geminal Diols: Synthesis, Structures, Stability and
 Photophysical Properties
;
_journal_name_full               'Chemical Science'
_journal_paper_doi               10.1039/D5SC08216A
_journal_year                    2025
_chemical_formula_moiety         'C32 H32 O2'
_chemical_formula_sum            'C32 H32 O2'
_chemical_formula_weight         448.57
_chemical_name_common            ketal-2Me-[1,1][2]PCP
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2023-01-03
_audit_creation_method
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_audit_update_record
;
2025-08-11 deposited with the CCDC.	2025-11-12 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.977(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   9.2334(3)
_cell_length_b                   11.3728(3)
_cell_length_c                   47.2982(14)
_cell_measurement_reflns_used    9882
_cell_measurement_temperature    298.15
_cell_measurement_theta_max      56.66
_cell_measurement_theta_min      3.48
_cell_volume                     4963.8(3)
_computing_cell_refinement       'SAINT V8.40B (?, 2016)'
_computing_data_reduction        'SAINT V8.40B (?, 2016)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      298.15
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0766
_diffrn_reflns_av_unetI/netI     0.0817
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       56
_diffrn_reflns_limit_l_min       -56
_diffrn_reflns_number            39114
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.027
_diffrn_reflns_theta_max         25.027
_diffrn_reflns_theta_min         0.862
_diffrn_source_current           1.4
_diffrn_source_power             0.07
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_T_max  0.7512
_exptl_absorpt_correction_T_min  0.6295
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1741 before and 0.0581 after correction.
The Ratio of minimum to maximum transmission is 0.8380.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.200
_exptl_crystal_description       block
_exptl_crystal_F_000             1920
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_refine_diff_density_max         0.255
_refine_diff_density_min         -0.207
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       0.0080(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     622
_refine_ls_number_reflns         8707
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.069
_refine_ls_R_factor_all          0.1315
_refine_ls_R_factor_gt           0.0650
_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^)+(0.1066P)^2^+0.2196P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1719
_refine_ls_wR_factor_ref         0.2070
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4802
_reflns_number_total             8707
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d5sc08216a2.cif
_cod_data_source_block           2
_cod_database_code               1576260
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.992
_shelx_estimated_absorpt_t_min   0.991
_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.a Secondary CH2 refined with riding coordinates:
 C61(H61A,H61B), C63(H63A,H63B), C29(H29A,H29B), C31(H31A,H31B)
2.b Aromatic/amide H refined with riding coordinates:
 C35(H35), C36(H36), C37(H37), C38(H38), C41(H41), C42(H42), C43(H43),
 C44(H44), C50(H50), C51(H51), C52(H52), C53(H53), C56(H56), C57(H57), C58(H58),
  C59(H59), C3(H3), C4(H4), C5(H5), C6(H6), C9(H9), C10(H10), C11(H11),
 C12(H12), C18(H18), C19(H19), C20(H20), C21(H21), C24(H24), C25(H25), C26(H26),
  C27(H27)
2.c Idealised Me refined as rotating group:
 C47(H47A,H47B,H47C), C48(H48A,H48B,H48C), C62(H62A,H62B,H62C), C64(H64A,H64B,
 H64C), C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C30(H30A,H30B,H30C), C32(H32A,
 H32B,H32C)
;
_shelx_res_checksum              75402
_olex2_submission_special_instructions 'No special instructions were received'