Controllable Self-Assembly of Macrocycles in Water for Isolating Aromatic Hydrocarbon Isomers.
Wu, Guangcheng; Wang, Cai-Yun; Jiao, Tianyu; Zhu, Huangtianzhi; Huang, Feihe; Li, Hao; Journal of the American Chemical Society 140 (2018) 5955–5961; doi:10.1021/jacs.8b01651

data_4132113
_publ_section_title
;
 Controllable Self-Assembly of Macrocycles in Water for Isolating Aromatic
 Hydrocarbon Isomers.
;
_journal_issue                   18
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              5955
_journal_page_last               5961
_journal_paper_doi               10.1021/jacs.8b01651
_journal_volume                  140
_journal_year                    2018
_chemical_formula_moiety         'O4 S, C35 H34 N6 O2'
_chemical_formula_sum            'C35 H34 N6 O6 S'
_chemical_formula_weight         666.74
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-01-09
_audit_creation_method
;
Olex2 1.2
(compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381)
;
_cell_angle_alpha                74.526(4)
_cell_angle_beta                 85.761(3)
_cell_angle_gamma                67.151(3)
_cell_formula_units_Z            2
_cell_length_a                   12.3237(6)
_cell_length_b                   13.4102(7)
_cell_length_c                   13.7397(6)
_cell_measurement_reflns_used    4042
_cell_measurement_temperature    170(2)
_cell_measurement_theta_max      50.286
_cell_measurement_theta_min      2.906
_cell_volume                     2015.52(18)
_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      170.0
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.991
_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  0.0617
_diffrn_reflns_av_unetI/netI     0.0688
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            24686
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        53.594
_diffrn_reflns_theta_max         54.964
_diffrn_reflns_theta_min         2.905
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.711
_exptl_absorpt_correction_T_max  0.7508
_exptl_absorpt_correction_T_min  0.5016
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 TWINABS-2012/1 (Bruker,2012) was used for absorption correction.
 
For component 1:
 wR2(int) was 0.1200 before and 0.0738 after correction.
 The Ratio of minimum to maximum transmission not present.
 The \l/2 correction factor is Not present
 
For component 2:
 wR2(int) was 0.1668 before and 0.0870 after correction.
 The Ratio of minimum to maximum transmission is 0.67.
 The \l/2 correction factor is Not present

Final HKLF 4 output contains 44577 reflections, Rint = 0.1006
 (13122 with I > 3sig(I), Rint = 0.0807)
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.099
_exptl_crystal_description       block
_exptl_crystal_F_000             700
_exptl_crystal_size_max          0.03
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.01
_refine_diff_density_max         1.768
_refine_diff_density_min         -0.686
_refine_diff_density_rms         0.123
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.670
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     460
_refine_ls_number_reflns         7612
_refine_ls_number_restraints     77
_refine_ls_restrained_S_all      1.707
_refine_ls_R_factor_all          0.2012
_refine_ls_R_factor_gt           0.1579
_refine_ls_shift/su_max          0.024
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.4367
_refine_ls_wR_factor_ref         0.4692
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4296
_reflns_number_total             7612
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja8b01651_si_003.cif
_cod_data_source_block           mjl18008_0m
_cod_database_code               4132113
_shelx_shelxl_version_number     2017/1
_shelx_estimated_absorpt_t_max   0.993
_shelx_estimated_absorpt_t_min   0.979
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2. Restrained distances
 S1-O5 = S1-O8 = S1-O3 = S1-O4
 1.5 with sigma of 0.02
 S1-O8 = S1-O5 = S2-O6 = S1-O3 = S1-O4 = S2-O3 = S2-O7
 1.48 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
S1 \\sim O3 \\sim O4 \\sim S2 \\sim O6 \\sim O7 \\sim O8 \\sim O5: within 2A
with sigma of 0.01 and sigma for terminal atoms of 0.02
4. Others
 Fixed Sof: S1(0.5) S2(0.5) O6(0.5) O7(0.5) O8(0.5) O5(0.5)
5.a Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B), C5(H5A,H5B), C6(H6A,H6B), C18(H18A,
 H18B), C25(H25A,H25B)
5.b Aromatic/amide H refined with riding coordinates:
 N1(H1), N3(H3), C8(H8), C10(H10), C11(H11), C12(H12), C14(H14), C15(H15),
 C16(H16), C20(H20), C21(H21), C23(H23), C24(H24), C26(H26), C27(H27), C30(H30),
  C31(H31), C32(H32), C34(H34), C35(H35)
;
_shelx_res_checksum              85820
_shelx_hkl_checksum              37625
_shelx_fab_checksum              20342
_olex2_submission_special_instructions 'No special instructions were received'