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_4035125
_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_absolute_configuration unk
_chemical_formula_moiety
'C22 H22 N4 O4, 1(O), 2(C2 H3 O2), 2(H2 O), 2(C16 H36 N)'
_chemical_formula_sum            'C58 H106 N6 O11'
_chemical_formula_weight         1063.48
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_Hall           'C -2yc'
_space_group_name_H-M_alt        'C 1 c 1'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2015-08-18
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_cell_angle_alpha                90
_cell_angle_beta                 90.113(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.782(2)
_cell_length_b                   17.2873(18)
_cell_length_c                   19.209(2)
_cell_measurement_reflns_used    4252
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      24.12
_cell_measurement_theta_min      2.168
_cell_volume                     6237.0(11)
_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      99.98
_diffrn_detector_area_resol_mean 8
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area detector'
_diffrn_measurement_method       '\w and \f scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0682
_diffrn_reflns_av_unetI/netI     0.0867
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            35902
_diffrn_reflns_point_group_measured_fraction_full 0.921
_diffrn_reflns_point_group_measured_fraction_max 0.921
_diffrn_reflns_theta_full        25.498
_diffrn_reflns_theta_max         25.498
_diffrn_reflns_theta_min         1.601
_diffrn_source                   'sealed tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6571
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0571 before and 0.0519 after correction.
The Ratio of minimum to maximum transmission is 0.8814.
The \l/2 correction factor is 0.0015.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.133
_exptl_crystal_description       block
_exptl_crystal_F_000             2336
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.07
_refine_diff_density_max         0.567
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.056
_refine_ls_abs_structure_details
;
 Flack x determined using 2092 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(6)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.015
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     721
_refine_ls_number_reflns         10699
_refine_ls_number_restraints     64
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.1363
_refine_ls_R_factor_gt           0.0720
_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^)+(0.1110P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1718
_refine_ls_wR_factor_ref         0.2018
_reflns_Friedel_coverage         0.841
_reflns_Friedel_fraction_full    0.843
_reflns_Friedel_fraction_max     0.843
_reflns_number_gt                6284
_reflns_number_total             10699
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            jo8b01481_si_001.cif
_cod_data_source_block           1TBAOAc
_cod_original_cell_volume        6236.9(12)
_cod_database_code               4035125
_shelx_estimated_absorpt_t_max   0.995
_shelx_estimated_absorpt_t_min   0.985
_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,H) groups
2. Restrained distances
 H10B-O7
 1.953 with sigma of 0.001
 H10A-O6
 2.091 with sigma of 0.001
 O8-C25
 1.25 with sigma of 0.02
 O8A-C25
 1.25 with sigma of 0.02
 O7-C25
 1.25 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(O11) \\sim Ueq, Uanis(O11A) \\sim Ueq, Uanis(O11B) \\sim Ueq: with sigma
of 0.005 and sigma for terminal atoms of 0.005
Uanis(O8) \\sim Ueq, Uanis(O8A) \\sim Ueq: with sigma of 0.002 and sigma for
terminal atoms of 0.002
4. Rigid body (RIGU) restrains
 O7, O8, O8A, C25, C26
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
5. Others
 Fixed Sof: O11(0.33333) O11B(0.33333) O11A(0.33333) O8(0.5) O8A(0.5)
6.a Free rotating group:
 O10(H10A,H10B), O9(H9A,H9B)
6.b Secondary CH2 refined with riding coordinates:
 C43(H43A,H43B), C44(H44A,H44B), C45(H45A,H45B), C47(H47A,H47B), C48(H48A,
 H48B), C49(H49A,H49B), C51(H51A,H51B), C52(H52A,H52B), C53(H53A,H53B),
 C55(H55A,H55B), C56(H56A,H56B), C57(H57A,H57B), C27(H27A,H27B), C28(H28A,H28B),
  C29(H29A,H29B), C31(H31A,H31B), C32(H32A,H32B), C33(H33A,H33B), C35(H35A,
 H35B), C36(H36A,H36B), C37(H37A,H37B), C39(H39A,H39B), C40(H40A,H40B),
 C41(H41A,H41B)
6.c Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2), C3(H3), N3(H3A), C4(H4), N4(H4A), C6(H6), C7(H7), C10(H10),
 C11(H11), C12(H12), C14(H14), C17(H17), C18(H18), C20(H20), C21(H21)
6.d Idealised Me refined as rotating group:
 C1(H1A,H1B,H1C), C22(H22A,H22B,H22C), C24(H24A,H24B,H24C), C26(H26A,H26B,
 H26C), C46(H46A,H46B,H46C), C50(H50A,H50B,H50C), C54(H54A,H54B,H54C), C58(H58A,
 H58B,H58C), C30(H30A,H30B,H30C), C34(H34A,H34B,H34C), C38(H38A,H38B,H38C),
 C42(H42A,H42B,H42C)
;
_shelx_res_checksum              51374
_shelx_hkl_checksum              4909
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'