Solution-State Anion Recognition, and Structural Studies, of a Series of Electron-Rich meta-Phenylene Bis(phenylurea) Receptors and Their Self-Assembled Structures.
Gillen, Dermot M.; Hawes, Chris S.; Gunnlaugsson, Thorfinnur; The Journal of organic chemistry 83 (2018) 10398–10408; doi:10.1021/acs.joc.8b01481

data_4035126
_publ_section_title
;
 Solution-State Anion Recognition, and Structural Studies, of a Series of
 Electron-Rich meta-Phenylene Bis(phenylurea) Receptors and Their
 Self-Assembled Structures.
;
_journal_issue                   17
_journal_name_full               'The Journal of organic chemistry'
_journal_page_first              10398
_journal_page_last               10408
_journal_paper_doi               10.1021/acs.joc.8b01481
_journal_volume                  83
_journal_year                    2018
_chemical_formula_moiety
'6(C22 H22 N4 O4), 6(C16 H36 N), 2(C0.5 H0.5 Cl1.5), 4(H1.5 O4 P1)'
_chemical_formula_sum            'C229 H355 Cl3 N30 O40 P4'
_chemical_formula_weight         4398.64
_space_group_crystal_system      trigonal
_space_group_IT_number           161
_space_group_name_Hall           'R 3 -2"c'
_space_group_name_H-M_alt        'R 3 c :H'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2015-06-27
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            3
_cell_length_a                   22.0110(7)
_cell_length_b                   22.0110(7)
_cell_length_c                   42.9761(14)
_cell_measurement_reflns_used    9515
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      24.35
_cell_measurement_theta_min      2.84
_cell_volume                     18031.7(10)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_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  0.0611
_diffrn_reflns_av_unetI/netI     0.0412
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       57
_diffrn_reflns_limit_l_min       -57
_diffrn_reflns_number            70836
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         28.330
_diffrn_reflns_theta_min         1.850
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.140
_exptl_absorpt_correction_T_max  0.4311
_exptl_absorpt_correction_T_min  0.3676
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
 wR2(int) was 0.0647 before and 0.0581 after correction. The Ratio 
 of minimum to maximum transmission is 0.8781. The \l/2 correction
 factor is 0.00150.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.215
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             7110
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.18
_refine_diff_density_max         0.429
_refine_diff_density_min         -0.493
_refine_diff_density_rms         0.058
_refine_ls_abs_structure_details
;
 Flack x determined using 3146 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.11(3)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     474
_refine_ls_number_reflns         9954
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0792
_refine_ls_R_factor_gt           0.0550
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.0960P)^2^+9.3580P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1422
_refine_ls_wR_factor_ref         0.1612
_reflns_Friedel_coverage         0.993
_reflns_Friedel_fraction_full    0.998
_reflns_Friedel_fraction_max     0.993
_reflns_number_gt                7602
_reflns_number_total             9954
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b01481_si_001.cif
_cod_data_source_block           3(TBA3H3P2O8)
_cod_original_cell_volume        18031.7(13)
_cod_original_sg_symbol_H-M      'R 3 c'
_cod_database_code               4035126
_shelx_estimated_absorpt_t_max   0.975
_shelx_estimated_absorpt_t_min   0.955
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 H6-O7
 1.74 with sigma of 0.01
 H7A-O6
 1.74 with sigma of 0.01
3. Others
 Fixed Sof: Cl1(0.5) H7A(0.5) H6(0.5) C39(0.16667) H39(0.16667)
4.a Ternary CH refined with riding coordinates:
 C39(H39)
4.b Secondary CH2 refined with riding coordinates:
 C24(H24A,H24B), C25(H25A,H25B), C26(H26A,H26B), C27(H27A,H27B), C28(H28A,
 H28B), C29(H29A,H29B), C32(H32A,H32B), C33(H33A,H33B), C34(H34A,H34B),
 C35(H35A,H35B), C36(H36A,H36B), C37(H37A,H37B)
4.c Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), C3(H3), N3(H3A), C4(H4), N4(H4A), C5(H5), C7(H7), C10(H10),
 C11(H11), C12(H12), C14(H14), C17(H17), C19(H19), C20(H20), C21(H21)
4.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C22(H22A,H22B,H22C), C23(H23A,H23B,H23C), C30(H30A,H30B,
 H30C), C31(H31A,H31B,H31C), C38(H38A,H38B,H38C)
4.e Idealised tetrahedral OH refined as rotating group:
 O7(H7A), O6(H6)
;
_shelx_res_checksum              81861
_shelx_hkl_checksum              14604
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'