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_4129461
_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), C68 H112 N4 O8, C4 F8 I2, C4 H8 O2, C H Cl3'
_chemical_formula_sum            'C77 H121 Br4 Cl3 F8 I2 N4 O10'
_chemical_formula_weight         2094.56
_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     iterative
_audit_creation_date             2015-02-23
_audit_creation_method
;
Olex2 1.2
(compiled 2014.05.21 svn.r2940 for OlexSys, GUI svn.r4846)
;
_cell_angle_alpha                77.6713(14)
_cell_angle_beta                 89.4968(15)
_cell_angle_gamma                82.9410(14)
_cell_formula_units_Z            4
_cell_length_a                   12.4020(2)
_cell_length_b                   22.5922(3)
_cell_length_c                   33.1865(6)
_cell_measurement_reflns_used    26237
_cell_measurement_temperature    123.01(10)
_cell_measurement_theta_max      76.5400
_cell_measurement_theta_min      3.7840
_cell_volume                     9013.7(3)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_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
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      123.01(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3953
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measurement_details
;
  1 omega   90.00  145.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   45.0000    0.0000 55

  2 omega   62.00   99.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000 -120.0000 37

  3 omega   57.00   84.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000  -60.0000 27

  4 omega   42.00   83.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000   30.0000 41

  5 omega   46.00  106.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -94.0000   60.0000 60

  6 omega   41.00  116.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -77.0000  150.0000 75

  7 omega   37.00   91.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -30.0000  120.0000 54

  8 omega   38.00  113.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -111.0000   30.0000 75

  9 omega   79.00  106.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -111.0000  -90.0000 27

 10 omega   46.00   95.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -45.0000 -180.0000 49

 11 omega   30.00   95.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -94.0000  -60.0000 65

 12 omega   36.00   82.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.9013 -125.0000   60.0000 46

 13 omega   36.00  116.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -111.0000  150.0000 80

 14 omega   24.00  172.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000    0.0000  -30.0000 148

 15 omega  143.00  175.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   77.0000 -180.0000 32

 16 omega   59.00  103.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  178.0000 -120.0000 44

 17 omega  -41.00   -3.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.9013   37.0000 -180.0000 38

 18 omega  -29.00   31.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.9013   37.0000 -150.0000 60

 19 omega  -49.00   28.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.9013   37.0000    0.0000 77

 20 omega   43.00   98.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.9013 -125.0000 -120.0000 55

 21 omega -109.00  -19.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.9013  -37.0000   30.0000 90

 22 omega -106.00  -69.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.9013 -146.0000  146.0000 37
;
_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      -0.0203141000
_diffrn_orient_matrix_UB_12      0.0204182000
_diffrn_orient_matrix_UB_13      -0.0469291000
_diffrn_orient_matrix_UB_21      -0.1225701000
_diffrn_orient_matrix_UB_22      -0.0029096000
_diffrn_orient_matrix_UB_23      0.0064171000
_diffrn_orient_matrix_UB_31      -0.0153561000
_diffrn_orient_matrix_UB_32      0.0672500000
_diffrn_orient_matrix_UB_33      0.0038847000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0333
_diffrn_reflns_av_unetI/netI     0.0478
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            70359
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.909
_diffrn_reflns_theta_min         3.592
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    8.966
_exptl_absorpt_correction_T_max  0.387
_exptl_absorpt_correction_T_min  0.192
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
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    1.543
_exptl_crystal_description       block
_exptl_crystal_F_000             4240
_exptl_crystal_size_max          0.3176
_exptl_crystal_size_mid          0.2265
_exptl_crystal_size_min          0.1639
_refine_diff_density_max         2.229
_refine_diff_density_min         -1.334
_refine_diff_density_rms         0.121
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     2042
_refine_ls_number_reflns         36988
_refine_ls_number_restraints     84
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0624
_refine_ls_R_factor_gt           0.0527
_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^)+(0.0712P)^2^+18.8574P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1364
_refine_ls_wR_factor_ref         0.1452
_reflns_Friedel_coverage         0.000
_reflns_number_gt                31248
_reflns_number_total             36988
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            ja5b06590_si_006.cif
_cod_data_source_block           6-CHCl3@2-5_1
_cod_original_cell_volume        9013.8(3)
_cod_database_code               4129461
_shelxl_version_number           2013-4
_chemical_oxdiff_formula         'C80 H80 O8 N4 Br4 F8 I2 Cl3'
_reflns_odcompleteness_completeness 99.89
_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 C(H,H,H,H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All C(H,H,H,H,H,H) groups, All O(H) groups
2. Restrained distances
 C59-C60 \\sim C59-C60B \\sim C62-C63 \\sim C62B-C63 \\sim C81-C82 \\sim
C81-C82B \\sim C84-C85 \\sim C84B-
 C85 \\sim C83B-C84B
 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
Uanis(C82) \\sim Ueq, Uanis(C82B) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(F15) \\sim Ueq, Uanis(F16) \\sim Ueq, Uanis(Cl1B) \\sim Ueq, Uanis(C60)
\\sim Ueq, Uanis(C60B) \\sim Ueq, Uanis(Cl1) \\sim Ueq: with sigma of 0.005 and
sigma for terminal atoms of 0.01
4. Others
 Sof(H59C)=Sof(H59D)=Sof(C60B)=Sof(H60C)=Sof(H60D)=Sof(C61B)=Sof(H61C)=
 Sof(H61D)=Sof(C62B)=Sof(H62C)=Sof(H62D)=Sof(H63C)=Sof(H63D)=1-FVAR(1)
 Sof(H59A)=Sof(H59B)=Sof(C60)=Sof(H60A)=Sof(H60B)=Sof(C61)=Sof(H61A)=Sof(H61B)=
 Sof(C62)=Sof(H62A)=Sof(H62B)=Sof(H63A)=Sof(H63B)=FVAR(1)
 Sof(H81C)=Sof(H81D)=Sof(C82B)=Sof(H82C)=Sof(H82D)=Sof(C83B)=Sof(H83C)=
 Sof(H83D)=Sof(C84B)=Sof(H84C)=Sof(H84D)=Sof(H85D)=Sof(H85E)=Sof(H85F)=1-FVAR(2)
 Sof(H81A)=Sof(H81B)=Sof(C82)=Sof(H82A)=Sof(H82B)=Sof(C83)=Sof(H83A)=Sof(H83B)=
 Sof(C84)=Sof(H84A)=Sof(H84B)=Sof(H85A)=Sof(H85B)=Sof(H85C)=FVAR(2)
 Sof(H15C)=Sof(Cl1B)=1-FVAR(3)
 Sof(H153)=Sof(Cl1)=FVAR(3)
5.a Ternary CH refined with riding coordinates:
 C14(H14D), C31(H31), C48(H48), C65(H65), C86(H86), C103(H103), C120(H120),
 C137(H137), C153(H153), C153(H15C), C154(H154)
5.b Secondary CH2 refined with riding coordinates:
 C7(H7C,H7D), C8(H8C,H8D), C9(H9A,H9B), C10(H10O,H10P), C11(H11P,H11Q),
 C12(H12H,H12I), C15(H15A,H15B), C16(H16A,H16B), C24(H24A,H24B), C25(H25A,H25B),
  C26(H26A,H26B), C27(H27A,H27B), C28(H28A,H28B), C29(H29A,H29B), C32(H32A,
 H32B), C33(H33A,H33B), C41(H41A,H41B), C42(H42A,H42B), C43(H43A,H43B),
 C44(H44A,H44B), C45(H45A,H45B), C46(H46A,H46B), C49(H49A,H49B), C50(H50A,H50B),
  C58(H58A,H58B), C59(H59A,H59B), C59(H59C,H59D), C60(H60A,H60B), C60B(H60C,
 H60D), C61(H61A,H61B), C61B(H61C,H61D), C62(H62A,H62B), C62B(H62C,H62D),
 C63(H63A,H63B), C63(H63C,H63D), C66(H66A,H66B), C67(H67A,H67B), N1(H1A,H1B),
 N2(H2A,H2B), N3(H3A,H3B), N4(H4A,H4B), C79(H79A,H79B), C80(H80A,H80B),
 C81(H81A,H81B), C81(H81C,H81D), C82(H82A,H82B), C82B(H82C,H82D), C83(H83A,
 H83B), C83B(H83C,H83D), C84(H84A,H84B), C84B(H84C,H84D), C87(H87A,H87B),
 C88(H88A,H88B), C96(H96A,H96B), C97(H97A,H97B), C98(H98A,H98B), C99(H99A,H99B),
  C100(H10A,H10B), C101(H10C,H10D), C104(H10H,H10I), C105(H10J,H10K), C113(H11A,
 H11B), C114(H11C,H11D), C115(H11E,H11F), C116(H11G,H11H), C117(H11I,H11J),
 C118(H11K,H11L), C121(H12A,H12B), C122(H12C,H12D), C130(H13A,H13B), C131(H13C,
 H13D), C132(H13E,H13F), C133(H13G,H13H), C134(H13I,H13J), C135(H13K,H13L),
 C138(H13P,H13Q), C139(H13R,H13S), N5(H5A,H5B), N6(H6A,H6B), N7(H7A,H7B),
 N8(H8A,H8B), C69(H69A,H69B), C70(H70A,H70B), C71(H71A,H71B), C72(H72A,H72B),
 C141(H14E,H14F), C142(H14G,H14H), C143(H14I,H14J), C144(H14K,H14L)
5.c Me refined with riding coordinates:
 C85(H85A,H85B,H85C), C85(H85D,H85E,H85F)
5.d Aromatic/amide H refined with riding coordinates:
 C6(H6), C23(H23), C40(H40), C57(H57), C78(H78), C95(H95), C112(H112),
 C129(H129)
5.e Idealised Me refined as rotating group:
 C13(H13T,H13U,H13V), C17(H17A,H17B,H17C), C30(H30A,H30B,H30C), C34(H34A,H34B,
 H34C), C47(H47A,H47B,H47C), C51(H51A,H51B,H51C), C64(H64A,H64B,H64C), C68(H68A,
 H68B,H68C), C89(H89A,H89B,H89C), C102(H10E,H10F,H10G), C106(H10L,H10M,H10N),
 C119(H11M,H11N,H11O), C123(H12E,H12F,H12G), C136(H13M,H13N,H13O), C140(H14A,
 H14B,H14C)
5.f Idealised tetrahedral OH refined as rotating group:
 O1(H1), O2(H2), O3(H3), O4(H4), O5(H5), O6(H6C), O7(H7), O8(H8), O11(H11),
 O12(H12), O13(H13), O14(H14), O15(H15), O16(H16), O17(H17), O18(H18)
;
_olex2_submission_special_instructions 'No special instructions were received'