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_4129464
_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
'4(Br), C2.56 F3.74 I0.7, C56 H88 N4 O8, 3(C4 H8 O2), C2.74 F4.14 I1.2, 0.5(I)'
_chemical_formula_sum            'C73.3 H112 Br4 F7.88 I2.4 N4 O14'
_chemical_formula_weight         2047.18
_space_group_crystal_system      orthorhombic
_space_group_IT_number           68
_space_group_name_Hall           '-C 2a 2ac'
_space_group_name_H-M_alt        'C c c a :2'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2015-06-23
_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                90
_cell_formula_units_Z            8
_cell_length_a                   24.2579(12)
_cell_length_b                   25.5595(12)
_cell_length_c                   30.1104(11)
_cell_measurement_reflns_used    8564
_cell_measurement_temperature    123.00(10)
_cell_measurement_theta_max      66.8490
_cell_measurement_theta_min      3.4560
_cell_volume                     18669.0(14)
_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)'
_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 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
  1 omega  -49.00   33.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.6513   37.0000 -150.0000 82

  2 omega   -5.00   49.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       41.6513  -77.0000  -30.0000 54

  3 omega   76.00  177.00   1.0000   90.0000
omega____ theta____ kappa____ phi______ frames
    -      105.0818   61.0000 -120.0000 101

  4 omega   29.00   73.00   1.0000   90.0000
omega____ theta____ kappa____ phi______ frames
    -      105.0818  -30.0000  -90.0000 44

  5 omega   87.00  177.00   1.0000   90.0000
omega____ theta____ kappa____ phi______ frames
    -      105.0818   61.0000    0.0000 90

  6 omega -118.00   -9.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.6513  -77.0000  120.0000 109

  7 omega -118.00   -9.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.6513  -77.0000 -120.0000 109

  8 omega   32.00  121.00   1.0000   90.0000
omega____ theta____ kappa____ phi______ frames
    -      105.0818 -125.0000   90.0000 89

  9 omega   72.00  100.00   1.0000   90.0000
omega____ theta____ kappa____ phi______ frames
    -      105.0818   77.0000   60.0000 28
;
_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      0.0503445000
_diffrn_orient_matrix_UB_12      -0.0260504000
_diffrn_orient_matrix_UB_13      0.0219839000
_diffrn_orient_matrix_UB_21      0.0109355000
_diffrn_orient_matrix_UB_22      -0.0311834000
_diffrn_orient_matrix_UB_23      -0.0429127000
_diffrn_orient_matrix_UB_31      0.0370274000
_diffrn_orient_matrix_UB_32      0.0446032000
_diffrn_orient_matrix_UB_33      -0.0171208000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0800
_diffrn_reflns_av_unetI/netI     0.0475
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_l_max       34
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            34843
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        66.750
_diffrn_reflns_theta_max         66.748
_diffrn_reflns_theta_min         3.644
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    8.931
_exptl_absorpt_correction_T_max  0.286
_exptl_absorpt_correction_T_min  0.121
_exptl_absorpt_correction_type   gaussian
_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)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
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    1.457
_exptl_crystal_description       block
_exptl_crystal_F_000             8239
_exptl_crystal_size_max          0.2434
_exptl_crystal_size_mid          0.218
_exptl_crystal_size_min          0.1658
_refine_diff_density_max         0.974
_refine_diff_density_min         -0.788
_refine_diff_density_rms         0.143
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     504
_refine_ls_number_reflns         8265
_refine_ls_number_restraints     126
_refine_ls_restrained_S_all      1.110
_refine_ls_R_factor_all          0.1662
_refine_ls_R_factor_gt           0.1279
_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^)+(0.1100P)^2^+190.0000P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.3136
_refine_ls_wR_factor_ref         0.3422
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4618
_reflns_number_total             8265
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja5b06590_si_009.cif
_cod_data_source_block           6@3b-5_2
_cod_original_sg_symbol_Hall     '-C 2b 2bc'
_cod_original_sg_symbol_H-M      'C c c e'
_cod_original_formula_sum        'C73.30 H112 Br4 F7.88 I2.40 N4 O14'
_cod_database_code               4129464
_shelxl_version_number           2013-4
_chemical_oxdiff_formula         'C80 H80 N4 O12 F32 I4 Br4'
_reflns_odcompleteness_completeness 99.83
_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, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 C39A-C40A = C39B_$1-C39B = C40B_$1-C40B = C40C_$1-C40C = C39C_$1-C39C
 1.5 with sigma of 0.02
 C40A-O8A = O7A-C39A = O7C-C40B = O7C-C39B = O7B-C39C = O7B-C40C
 1.4 with sigma of 0.02
 C35-C36
 1.52 with sigma of 0.02
 C34-F2A
 1.43 with sigma of 0.02
 C34-F1A
 1.43 with sigma of 0.02
 C36-F4A
 1.43 with sigma of 0.02
 F3B-C36
 1.43 with sigma of 0.02
 C36-F4B
 1.43 with sigma of 0.02
 C36-F9
 1.43 with sigma of 0.02
 C35-F2B
 1.43 with sigma of 0.02
 F1B-C35
 1.43 with sigma of 0.02
 F1B-F2B
 2.2 with sigma of 0.02
 I1A-C34
 2 with sigma of 0.02
 C32-C33
 1.54 with sigma of 0.02
 C32-C32_$2
 1.54 with sigma of 0.02
 C32-F7A
 1.43 with sigma of 0.02
 C32-F8A
 1.43 with sigma of 0.02
 C32-F8B
 1.43 with sigma of 0.02
 C32-F7B
 1.43 with sigma of 0.02
 C33-F6B
 1.43 with sigma of 0.02
 C33-F5B
 1.43 with sigma of 0.02
 C1E-C1E_$3
 1.5 with sigma of 0.02
 O6-C1D
 1.4 with sigma of 0.02
 O6-C1E
 1.4 with sigma of 0.02
 C28-C27
 1.52 with sigma of 0.02
 H28A_$4-H28A
 2.1 with sigma of 0.02
 H14B_$5-H14B
 2.1 with sigma of 0.02
 C31-C32
 1.54 with sigma of 0.02
 C31-F5A
 1.43 with sigma of 0.02
 C31-F6A
 1.43 with sigma of 0.02
 H12B-H39E_$6 = H12B-H39A_$6
 2.1 with sigma of 0.01
 C28-C26
 2.54 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
C12 \\sim C13: within 1.7A with sigma of 0.02 and sigma for terminal atoms of
0.04
C26 \\sim C27 \\sim C28: within 1.7A with sigma of 0.01 and sigma for terminal
atoms of 0.02
Uanis(I1A) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C13) \\sim Ueq, Uanis(C10) \\sim Ueq, Uanis(C14) \\sim Ueq, Uanis(C27)
\\sim Ueq, Uanis(C28) \\sim Ueq, Uanis(C29) \\sim Ueq, Uanis(C30) \\sim Ueq,
Uanis(C29) \\sim Ueq, Uanis(C1E) \\sim Ueq, Uanis(C1D) \\sim Ueq, Uanis(O6)
\\sim Ueq: with sigma of 0.02 and sigma for terminal atoms of 0.04
Uanis(I2A) = Uanis(I2B) = Uanis(I2C)
4. Others
 Uiso(C39C)=Uiso(C40A)=Uiso(O7A)=Uiso(O7C)=Uiso(C39A)=Uiso(C40B)=Uiso(O8A)=
 Uiso(C40C)=Uiso(O7B)=Uiso(C39B)=FVAR(1)
 Fixed Sof: I2A(0.25) C39C(0.33333) H39C(0.33333) H39D(0.33333) C40A(0.33333)
 H40A(0.33333) H40B(0.33333) O7A(0.16667) O7C(0.33333) C39A(0.33333)
 H39A(0.33333) H39B(0.33333) C40B(0.33333) H40E(0.33333) H40F(0.33333) I1A(0.5)
 I2B(0.25) O8A(0.16667) C40C(0.33333) H40C(0.33333) H40D(0.33333) O7B(0.33333)
 C39B(0.33333) H39E(0.33333) H39F(0.33333) F6A(0.27) C31(0.22) F4A(0.32)
 C32(0.47) F7A(0.3) F8A(0.35) F9(0.28) C36(0.53) F5A(0.28) F6B(0.2) C33(0.59)
 F2A(0.28) F1A(0.33) I2C(0.1) F7B(0.16) I1B(0.1) C35(0.67) F2B(0.26) C34(0.17)
 F5B(0.11) F8B(0.2) F4B(0.29) F3B(0.24) F1B(0.07)
 Fixed Uiso: F6A(0.15) C31(0.15) F4A(0.15) C32(0.15) F7A(0.15) F8A(0.15)
 F9(0.15) C36(0.15) F5A(0.15) F6B(0.15) C33(0.15) F2A(0.15) F1A(0.15) F7B(0.15)
 C35(0.15) F2B(0.15) C34(0.15) F5B(0.15) F8B(0.15) F4B(0.15) F3B(0.15) F1B(0.15)
 Fixed X: F6B(0.578509) F5B(0.5337) F8B(0.668571)
 Fixed Y: F6B(0.28538) F5B(0.201409) F8B(0.27938)
 Fixed Z: F6B(0.17357) F5B(0.190201) F8B(0.20521)
5.a Ternary CH refined with riding coordinates:
 C25(H25), C11(H11)
5.b Secondary CH2 refined with riding coordinates:
 N1(H1A,H1B), N2(H2A,H2B), C8(H8A,H8B), C21(H21A,H21B), C9(H9A,H9B), C23(H23A,
 H23B), C22(H22A,H22B), C7(H7A,H7B), C12(H12A,H12B), C13(H13A,H13B), C39C(H39C,
 H39D), C40A(H40A,H40B), C39A(H39A,H39B), C40B(H40E,H40F), C40C(H40C,H40D),
 C39B(H39E,H39F), C29(H29A,H29B), C30(H30A,H30B), C27(H27A,H27B), C26(H26A,
 H26B), C1D(H1DA,H1DB), C1E(H1EA,H1EB)
5.c Aromatic/amide H refined with riding coordinates:
 C20(H20), C6(H6)
5.d Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C24(H24A,H24B,H24C), C14(H14A,H14B,H14C), C28(H28A,H28B,
 H28C)
5.e Idealised tetrahedral OH refined as rotating group:
 O4(H4), O2(H2), O1(H1), O3(H3)
;
_olex2_submission_special_instructions 'No special instructions were received'