π-Metalated [1<sub>5</sub>]Paracyclophanes: Synthesis and Binding to Oxo-Anions via Anion-π Interactions.
Zeng, Hong; Liu, Peiren; Feng, Guoqin; Huang, Feihe; Journal of the American Chemical Society 141 (2019) 16501–16511; doi:10.1021/jacs.9b09582

data_4127661
_publ_section_title
;
 \p-Metalated [1<sub>5</sub>]Paracyclophanes: Synthesis and Binding to
 Oxo-Anions via Anion-\p Interactions.
;
_journal_issue                   41
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              16501
_journal_page_last               16511
_journal_paper_doi               10.1021/jacs.9b09582
_journal_volume                  141
_journal_year                    2019
_chemical_formula_moiety         'C65 H72 Ru3, 5.5(C F3 O3 S), Cl0.5 O2'
_chemical_formula_sum            'C70.5 H72 Cl0.5 F16.5 O18.5 Ru3 S5.5'
_chemical_formula_weight         2026.04
_space_group_crystal_system      orthorhombic
_space_group_IT_number           62
_space_group_name_Hall           '-P 2ac 2n'
_space_group_name_H-M_alt        'P n m a'
_symmetry_space_group_name_Hall  '-P 2ac 2n'
_symmetry_space_group_name_H-M   'P n m a'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2019-08-08
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3510 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   16.2763(6)
_cell_length_b                   22.5468(7)
_cell_length_c                   24.1052(8)
_cell_measurement_reflns_used    9984
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      54.941
_cell_measurement_theta_min      2.851
_cell_volume                     8846.1(5)
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      169.99
_diffrn_measured_fraction_theta_full 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       '\f and \w scans'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0529
_diffrn_reflns_av_unetI/netI     0.0354
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            49585
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.972
_diffrn_reflns_theta_min         2.850
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    4.176
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.4514
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1306 before and 0.0791 after correction. The Ratio of minimum to maximum transmission is 0.6012. The \l/2 correction factor is Not present.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.521
_exptl_crystal_description       block
_exptl_crystal_F_000             4080
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         1.415
_refine_diff_density_min         -1.274
_refine_diff_density_rms         0.117
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     579
_refine_ls_number_reflns         8547
_refine_ls_number_restraints     215
_refine_ls_restrained_S_all      1.088
_refine_ls_R_factor_all          0.0709
_refine_ls_R_factor_gt           0.0648
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1289P)^2^+19.1532P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1961
_refine_ls_wR_factor_ref         0.2037
_reflns_Friedel_coverage         0.000
_reflns_number_gt                7453
_reflns_number_total             8547
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja9b09582_si_002.cif
_cod_data_source_block           190524zh_0m
_cod_original_formula_sum        'C70.50 H72 Cl0.50 F16.50 O18.50 Ru3 S5.50'
_cod_database_code               4127661
_shelx_shelxl_version_number     2014/7
_shelx_estimated_absorpt_t_max   0.680
_shelx_estimated_absorpt_t_min   0.573
_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
 S2-C38
 1.45 with sigma of 0.02
 Cl1-O2 = Cl1-O1
 1.45 with sigma of 0.02
 F7-C40 = F8-C40
 1.4 with sigma of 0.02
 O3-Cl1
 1.45 with sigma of 0.02
 O2_$1-O2
 2 with sigma of 0.02
 C34-C33 = C36-C34 = C34-C35
 1.53 with sigma of 0.02
 O3-O2_$1 \\sim O2_$1-O2
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
S2 \\sim C38 \\sim O7 \\sim O8 \\sim O9: within 2A with sigma of 0.01 and sigma
for terminal atoms of 0.02
S4 \\sim F8 \\sim F7 \\sim O12 \\sim O13 \\sim C40 \\sim Cl1 \\sim O1 \\sim O2:
within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02
O1 \\sim O2 \\sim O3: within 2A with sigma of 0.01 and sigma for terminal atoms
of 0.02
Cl1 \\sim O3: within 2A with sigma of 0.01 and sigma for terminal atoms of 0.02
C33 \\sim C34 \\sim C35 \\sim C36: within 2A with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(O3) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
Uanis(C33) \\sim Ueq, Uanis(C34) \\sim Ueq, Uanis(C35) \\sim Ueq, Uanis(C36)
\\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(F5) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C29) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
4. Others
 Fixed Sof: H29A(0.5) H29B(0.5) H29C(0.5) H34(0.5) H35A(0.5) H35B(0.5)
 H35C(0.5) H36A(0.5) H36B(0.5) H36C(0.5) S4(0.25) F8(0.25) F7(0.5) O12(0.25)
 O13(0.5) C40(0.25) Cl1(0.25) O1(0.25) O2(0.5) O3(0.25)
5.a Ternary CH refined with riding coordinates:
 C8(H8), C13(H13), C16(H16), C17(H17), C27(H27), C28(H28), C31(H31), C32(H32),
 C34(H34)
5.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C18(H18A,H18B), C25(H25A,H25B)
5.c Me refined with riding coordinates:
 C29(H29A,H29B,H29C)
5.d Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C7(H7), C14(H14), C20(H20), C21(H21), C23(H23),
 C24(H24)
5.e Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C9(H9A,H9B,H9C), C10(H10A,H10B,H10C), C35(H35A,H35B,H35C),
 C36(H36A,H36B,H36C)
;
_shelx_res_checksum              93974
_shelx_hkl_checksum              72543
_shelx_fab_checksum              44552
_olex2_submission_special_instructions 'No special instructions were received'