Enhanced molecular binding affinity toward aromatic dications by anthracene-derived crown ethers in water.
Zhou, Jia-Liang; Li, Yan-Hong; Zhang, Ying-Ming; Chen, Ling; Liu, Yu; Organic & biomolecular chemistry 21 (2022) 107–114; doi:10.1039/d2ob02010f

data_7159028
_publ_section_title
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 Enhanced molecular binding affinity toward aromatic dications by
 anthracene-derived crown ethers in water.
;
_journal_issue                   1
_journal_name_full               'Organic &amp; biomolecular chemistry'
_journal_page_first              107
_journal_page_last               114
_journal_paper_doi               10.1039/d2ob02010f
_journal_volume                  21
_journal_year                    2022
_chemical_formula_moiety         '2(C44 H44 O22 S4), 2(C24 H28 N4), 9.25(H8 O4)'
_chemical_formula_sum            'C136 H218 N8 O81 S8'
_chemical_formula_weight         3517.65
_space_group_crystal_system      tetragonal
_space_group_IT_number           84
_space_group_name_Hall           '-P 4c'
_space_group_name_H-M_alt        'P 42/m'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2019-12-20
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2022-11-02 deposited with the CCDC.	2022-12-05 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   24.7343(13)
_cell_length_b                   24.7343(13)
_cell_length_c                   13.8021(11)
_cell_measurement_reflns_used    7165
_cell_measurement_temperature    150(2)
_cell_measurement_theta_max      25.788
_cell_measurement_theta_min      2.47
_cell_volume                     8443.9(9)
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_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    'SIR2004 (Burla et al.,  2007)'
_diffrn_ambient_temperature      150.0
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0939
_diffrn_reflns_av_unetI/netI     0.0752
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       32
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            53237
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.481
_diffrn_reflns_theta_min         1.880
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.207
_exptl_absorpt_correction_T_max  0.7469
_exptl_absorpt_correction_T_min  0.6226
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0757 before and 0.0595 after correction. The Ratio of minimum to maximum transmission is 0.8336. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            'brownish red'
_exptl_crystal_density_diffrn    1.384
_exptl_crystal_description       stick
_exptl_crystal_F_000             3732
_refine_diff_density_max         1.367
_refine_diff_density_min         -0.647
_refine_diff_density_rms         0.137
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.012
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     605
_refine_ls_number_reflns         10009
_refine_ls_number_restraints     117
_refine_ls_restrained_S_all      1.008
_refine_ls_R_factor_all          0.2687
_refine_ls_R_factor_gt           0.1676
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.4300P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.4756
_refine_ls_wR_factor_ref         0.5819
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4122
_reflns_number_total             10009
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d2ob02010f2.cif
_cod_data_source_block           TSDA42MV
_cod_depositor_comments          'Adding full bibliography for 7159028.cif.'
_cod_original_cell_volume        8443.9(11)
_cod_database_code               7159028
_shelx_shelxl_version_number     2014/7
_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, All O(H,H) groups
2. Restrained distances
 C44-N3
 1.49 with sigma of 0.01
3. Restrained planarity
 N4, C39, C40, C41, C42, C43, C45
 with sigma of 0.01
 N3, C34, C35, C36, C37, C38, C44
 with sigma of 0.01
4. Uiso/Uaniso restraints and constraints
N4 \\sim C39 \\sim C40 \\sim C41 \\sim C42 \\sim C43 \\sim C45: within 2A with
sigma of 0.001 and sigma for terminal atoms of 0.002
N3 \\sim C34 \\sim C35 \\sim C36 \\sim C37 \\sim C38 \\sim C44: within 2A with
sigma of 0.001 and sigma for terminal atoms of 0.002
Uanis(O8W) \\sim Ueq, Uanis(O13W) \\sim Ueq, Uanis(O14W) \\sim Ueq, Uanis(O16W)
\\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
5. Others
 Fixed Sof: H46A(0.5) H46B(0.5) H46C(0.5) H33A(0.5) H33B(0.5) H33C(0.5)
 C42(0.5) H42(0.5) C43(0.5) H43(0.5) N4(0.5) C39(0.5) H39(0.5) C40(0.5)
 H40(0.5) C41(0.5) C34(0.5) H34(0.5) C35(0.5) H35(0.5) C36(0.5) C37(0.5)
 H37(0.5) C38(0.5) H38(0.5) N3(0.5) C45(0.5) H45A(0.5) H45B(0.5) H45C(0.5)
 C44(0.5) H44A(0.5) H44B(0.5) H44C(0.5) H1WA(0.25) H1WB(0.25) H2WA(0.5)
 H2WB(0.5) H3WA(0.5) H3WB(0.5) H5WA(0.5) H5WB(0.5) H6WA(0.5) H6WB(0.5)
 H7WB(0.5) H8WA(0.5) H8WB(0.5) H9WA(0.5) H9WB(0.5) H10A(0.5) H10B(0.5)
 H11A(0.5) H11B(0.5) H13A(0.5)
6.a Riding coordinates:
 C45(H45A,H45B,H45C), C44(H44A,H44B,H44C), O1W(H1WA,H1WB), O2W(H2WA,H2WB),
 O3W(H3WA,H3WB), O4W(H4WA,H4WB), O5W(H5WA,H5WB), O6W(H6WA,H6WB), O7W(H7WA,H7WB),
  O8W(H8WA,H8WB), O9W(H9WA,H9WB), O10W(H10A,H10B), O11W(H11A,H11B), O12W(H12A,
 H12B), O13W(H13A,H13B), O14W(H14A,H14B), O16W(H16C,H16D)
6.b Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C15(H15A,H15B), C17(H17A,H17B), C18(H18A,H18B), C19(H19A,
 H19B), C22(H22A,H22B), C21(H21A,H21B), C20(H20A,H20B)
6.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C7(H7), C10(H10), C13(H13), C12(H12), C32(H32), C31(H31),
 C30(H30), C29(H29), C27(H27), C26(H26), C24(H24), C23(H23), C42(H42), C43(H43),
  C39(H39), C40(H40), C34(H34), C35(H35), C37(H37), C38(H38)
6.d Fitted hexagon refined as free rotating group:
 C42(C43,N4,C39,C40,C41), C34(C35,C36,C37,C38,N3)
6.e Idealised Me refined as rotating group:
 C46(H46A,H46B,H46C), C33(H33A,H33B,H33C)
;
_shelx_res_checksum              56144
_olex2_submission_special_instructions 'No special instructions were received'