Concerted Halogen-Bonded Networks with N-Alkyl Ammonium Resorcinarene Bromides: From Dimeric Dumbbell to Capsular Architectures.
Pan, Fangfang; Beyeh, Ngong Kodiah; Rissanen, Kari; Journal of the American Chemical Society 137 (2015) 10406–10413; doi:10.1021/jacs.5b06590

data_4129463
_publ_section_title
;
 Concerted Halogen-Bonded Networks with N-Alkyl Ammonium Resorcinarene
 Bromides: From Dimeric Dumbbell to Capsular Architectures.
;
_journal_issue                   32
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              10406
_journal_page_last               10413
_journal_paper_doi               10.1021/jacs.5b06590
_journal_volume                  137
_journal_year                    2015
_chemical_formula_moiety
'2(C2 F4 I2), 4(Br), C62 H82 N4 O8, C6 H8 O4, C4 H8 O2'
_chemical_formula_sum            'C76 H98 Br4 F8 I4 N4 O14'
_chemical_formula_weight         2270.82
_space_group_crystal_system      tetragonal
_space_group_IT_number           130
_space_group_name_Hall           '-P 4a 2ac'
_space_group_name_H-M_alt        'P 4/n c c :2'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_audit_creation_date             2015-03-09
_audit_creation_method
;
Olex2 1.2
(compiled 2014.05.21 svn.r2940 for OlexSys, GUI svn.r4846)
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   18.2858(13)
_cell_length_b                   18.2858(13)
_cell_length_c                   29.8612(9)
_cell_measurement_reflns_used    3167
_cell_measurement_temperature    123.00(10)
_cell_measurement_theta_max      69.9970
_cell_measurement_theta_min      3.8090
_cell_volume                     9984.7(10)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_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    'ShelXS (Sheldrick, 2008)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      123.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.1977
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.982
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details
;
  1 omega  -74.00   32.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.9013   77.0000   30.0000 106

  2 omega   24.00  108.00   1.0000  150.0000
omega____ theta____ kappa____ phi______ frames
    -      105.0818  -94.0000 -180.0000 84

  3 omega   32.00   68.00   1.0000  150.0000
omega____ theta____ kappa____ phi______ frames
    -      105.0818  -30.0000    0.0000 36

  4 omega   79.00  127.00   1.0000  150.0000
omega____ theta____ kappa____ phi______ frames
    -      105.0818  -61.0000  -60.0000 48

  5 omega   23.00  104.00   1.0000  150.0000
omega____ theta____ kappa____ phi______ frames
    -      105.0818  -15.0000   30.0000 81

  6 omega -115.00  -18.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.9013  -57.0000  -90.0000 97

  7 omega -118.00   -9.00   1.0000   25.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.9013  -77.0000   60.0000 109
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_UB_11      -0.0487311000
_diffrn_orient_matrix_UB_12      0.0683041000
_diffrn_orient_matrix_UB_13      -0.0044384000
_diffrn_orient_matrix_UB_21      -0.0684880000
_diffrn_orient_matrix_UB_22      -0.0491243000
_diffrn_orient_matrix_UB_23      -0.0013799000
_diffrn_orient_matrix_UB_31      -0.0060525000
_diffrn_orient_matrix_UB_32      0.0046310000
_diffrn_orient_matrix_UB_33      0.0513591000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.1420
_diffrn_reflns_av_unetI/netI     0.0545
_diffrn_reflns_Laue_measured_fraction_full 0.982
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            28088
_diffrn_reflns_point_group_measured_fraction_full 0.982
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         66.688
_diffrn_reflns_theta_min         3.418
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    12.252
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.08427
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.511
_exptl_crystal_description       plate
_exptl_crystal_F_000             4472
_exptl_crystal_size_max          0.1442
_exptl_crystal_size_mid          0.1021
_exptl_crystal_size_min          0.0656
_refine_diff_density_max         1.898
_refine_diff_density_min         -1.044
_refine_diff_density_rms         0.293
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.602
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     116
_refine_ls_number_reflns         4443
_refine_ls_number_restraints     51
_refine_ls_restrained_S_all      1.629
_refine_ls_R_factor_all          0.3203
_refine_ls_R_factor_gt           0.2404
_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^)+(0.2000P)^2^] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.5631
_refine_ls_wR_factor_ref         0.6355
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1112
_reflns_number_total             4443
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja5b06590_si_011.cif
_cod_data_source_block           6@4-5_2
_cod_original_cell_volume        9984.7(15)
_cod_original_sg_symbol_H-M      'P 4/n c c'
_cod_database_code               4129463
_shelxl_version_number           2013-4
_chemical_oxdiff_formula         'C20 H20 N1 O9 S1'
_reflns_odcompleteness_completeness 99.92
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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) groups
2. Shared sites
{C22, O3B}
{O3, C22B}
3. Restrained distances
 N1-C13
 2.54 with sigma of 0.02
 N1-C9
 2.54 with sigma of 0.02
 C13-C9
 2.52 with sigma of 0.02
 C8-C9 = C10-C11 = C12-C13
 1.52 with sigma of 0.02
 C9-C10 = C11-C12 = C13-C8
 1.52 with sigma of 0.02
 C8-C10 = C9-C11
 2.52 with sigma of 0.02
 C10-C12 = C11-C13
 2.52 with sigma of 0.02
 C8-C12
 2.52 with sigma of 0.02
 C8-C11 = C9-C12 = C10-C13
 2.85 with sigma of 0.02
 F1-I1
 2.9 with sigma of 0.02
 C18-C19
 1.52 with sigma of 0.02
 C19-C19_$1
 1.52 with sigma of 0.02
 C18-F2 = C19-F3
 1.34 with sigma of 0.02
 C19-F4 = C18-F1
 1.34 with sigma of 0.02
 F1-F2 = F4-F3
 2.4 with sigma of 0.02
 C18-I1
 2 with sigma of 0.02
 F2-F3
 2.7 with sigma of 0.02
 F1-F4
 2.7 with sigma of 0.02
 F2-I1
 2.9 with sigma of 0.02
 F4-C19_$1
 2.2 with sigma of 0.02
 F4_$1-C19
 2.2 with sigma of 0.02
 F2-F4
 2.7 with sigma of 0.02
 C19-F1
 2.2 with sigma of 0.02
 C23-O4
 1.45 with sigma of 0.02
 O5-O4
 2.78 with sigma of 0.02
 C24-C23
 1.5 with sigma of 0.02
 C23-O4 = C24-O5
 1.4 with sigma of 0.02
 O4-C24 = C23-O5
 2.4 with sigma of 0.02
 C24_$2-C23_$3
 2.8 with sigma of 0.02
 O3-C22
 1.45 with sigma of 0.02
 C20-C21
 2.8 with sigma of 0.02
 C22-C21
 1.4 with sigma of 0.02
 C20-C22
 2.4 with sigma of 0.02
 O3-C20
 1.45 with sigma of 0.02
 O3-C21
 2.4 with sigma of 0.02
 N1-C8
 1.5 with sigma of 0.02
 C4-O2 = C2-O1
 1.45 with sigma of 0.02
4. Uiso/Uaniso restraints and constraints
Uiso(O3) = Uiso(C22B)
Uiso(C22) = Uiso(O3B)
5. Others
 Fixed Sof: F2(0.5) F4(0.5) C19(0.5) F1(0.5) F3(0.5) C17(0.5) H17A(0.5)
 H17B(0.5) H17C(0.5) C18(0.5) C16(0.5) H16A(0.5) H16B(0.5) C15(0.5) H15A(0.5)
 H15B(0.5) C22(0.5) H22A(0.5) H22B(0.5) O3(0.5) O3B(0.5) C22B(0.5) H22C(0.5)
 H22D(0.5) C24(0.5) H24A(0.5) H24B(0.5) C23(0.5) H23A(0.5) H23B(0.5)
 Fixed Uiso: F2(0.2) F4(0.2) C19(0.2) F1(0.2) F3(0.2) C9(0.2) C13(0.2)
 C12(0.2) C8(0.2) C18(0.2) C11(0.2) C10(0.2) C21(0.2) C20(0.2) C22(0.2) O3(0.2)
 O3B(0.2) C22B(0.2) O4(0.2) C24(0.2) C23(0.2) O5(0.2)
6.a Riding coordinates:
 O1(H1), O2(H2)
6.b Ternary CH refined with riding coordinates:
 C14(H14), C8(H8)
6.c Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C9(H9A,H9B), C13(H13A,H13B), C12(H12A,H12B), C16(H16A,H16B),
 C15(H15A,H15B), C11(H11A,H11B), C10(H10A,H10B), C22(H22A,H22B), C22B(H22C,
 H22D), C24(H24A,H24B), C23(H23A,H23B)
6.d Aromatic/amide H refined with riding coordinates:
 C6(H6)
6.e Fitted hexagon refined as free rotating group:
 C1(C2,C3,C4,C5,C6)
6.f Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C)
;
_olex2_submission_special_instructions 'No special instructions were received'