Halogen-Bonded Solvates of Tetrahaloethynyl Cavitands
Turunen, Lotta; Pan, Fangfang; Beyeh, Ngong Kodiah; Cetina, Mario; Trant, John; Ras, Robin H.A.; Rissanen, Kari; CrystEngComm  (2017) –; doi:10.1039/C7CE01118K

data_7228808
_publ_section_title
;
 Halogen-Bonded Solvates of Tetrahaloethynyl Cavitands
;
_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/C7CE01118K
_journal_year                    2017
_chemical_formula_moiety         'C68 H76 I4 O8, 3.5(C3 H7 N O)'
_chemical_formula_sum            'C78.5 H100.5 I4 N3.5 O11.5'
_chemical_formula_weight         1784.72
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2017-07-04
_audit_creation_method
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5337)
;
_audit_update_record
;
2017-07-12 deposited with the CCDC.
2017-07-31 downloaded from the CCDC.
;
_cell_angle_alpha                90.053(2)
_cell_angle_beta                 92.142(2)
_cell_angle_gamma                97.4128(19)
_cell_formula_units_Z            4
_cell_length_a                   16.7987(4)
_cell_length_b                   20.0128(4)
_cell_length_c                   24.3284(7)
_cell_measurement_reflns_used    15558
_cell_measurement_temperature    123.00(10)
_cell_measurement_theta_max      73.2300
_cell_measurement_theta_min      3.6100
_cell_volume                     8104.8(3)
_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, 2015)'
_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 0.988
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_details
;
  1 omega  -96.00   -5.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.9013  125.0000  150.0000 91

  2 omega -122.00   -1.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.9013  -19.0000  -60.0000 121

  3 omega  -49.00   33.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.9013   37.0000  120.0000 82

  4 omega  102.00  178.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      105.0818  125.0000   60.0000 76

  5 omega   46.00  121.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      105.0818 -125.0000  -90.0000 75

  6 omega   29.00   82.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      105.0818  -30.0000    0.0000 53

  7 omega   31.00   91.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      105.0818  -30.0000   90.0000 60

  8 omega   33.00  109.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      105.0818  -94.0000    0.0000 76

  9 omega   84.00  178.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      105.0818   45.0000  120.0000 94

 10 omega   79.00  173.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      105.0818   45.0000   30.0000 94

 11 omega   94.00  162.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      105.0818  125.0000   30.0000 68

 12 omega   29.00   54.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      105.0818  -30.0000  150.0000 25

 13 omega -115.00  -14.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.9013  -57.0000 -120.0000 101

 14 omega -118.00   -9.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.9013  -77.0000   90.0000 109

 15 omega -115.00  -14.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.9013  -57.0000  150.0000 101

 16 omega   22.00  109.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      105.0818  -94.0000  120.0000 87

 17 omega   72.00  109.00   1.0000   40.0000
omega____ theta____ kappa____ phi______ frames
    -      105.0818   77.0000  150.0000 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      0.0823405000
_diffrn_orient_matrix_UB_12      -0.0013175000
_diffrn_orient_matrix_UB_13      -0.0255305000
_diffrn_orient_matrix_UB_21      -0.0335709000
_diffrn_orient_matrix_UB_22      0.0252167000
_diffrn_orient_matrix_UB_23      -0.0548741000
_diffrn_orient_matrix_UB_31      0.0256490000
_diffrn_orient_matrix_UB_32      0.0734071000
_diffrn_orient_matrix_UB_33      0.0187806000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0877
_diffrn_reflns_av_unetI/netI     0.1085
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            62988
_diffrn_reflns_point_group_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        66.750
_diffrn_reflns_theta_max         66.749
_diffrn_reflns_theta_min         3.160
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    12.537
_exptl_absorpt_correction_T_max  0.903
_exptl_absorpt_correction_T_min  0.807
_exptl_absorpt_correction_type   analytical
_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)
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    1.463
_exptl_crystal_description       needle
_exptl_crystal_F_000             3600
_exptl_crystal_size_max          0.1043
_exptl_crystal_size_mid          0.0723
_exptl_crystal_size_min          0.0393
_refine_diff_density_max         3.570
_refine_diff_density_min         -2.831
_refine_diff_density_rms         0.182
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1740
_refine_ls_number_reflns         28379
_refine_ls_number_restraints     105
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.1307
_refine_ls_R_factor_gt           0.0935
_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^)+(0.1773P)^2^+5.9991P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2546
_refine_ls_wR_factor_ref         0.3063
_reflns_Friedel_coverage         0.000
_reflns_number_gt                18131
_reflns_number_total             28379
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ce01118k2.cif
_cod_data_source_block           3_dmf
_cod_original_cell_volume        8104.7(4)
_cod_original_formula_sum        'C78.50 H100.50 I4 N3.50 O11.50'
_cod_database_code               7228808
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C64 H96 N16 O8 I4'
_reflns_odcompleteness_completeness 98.77
_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
2. Restrained distances
 H15N_$1-H83A
 2.2 with sigma of 0.02
 C130-C132 = C131-C133 = C132-C134
 2.5 with sigma of 0.02
 C130-C131 = C131-C132 = C132-C133 = C82-C83
 1.54 with sigma of 0.02
 C133-C134
 1.54 with sigma of 0.01
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
Uanis(C147) \\sim Ueq, Uanis(N7) \\sim Ueq, Uanis(C142) \\sim Ueq, Uanis(C144)
\\sim Ueq, Uanis(C82) \\sim Ueq, Uanis(C47) \\sim Ueq, Uanis(C154) \\sim Ueq:
with sigma of 0.01 and sigma for terminal atoms of 0.02
Uanis(C115) \\sim Ueq, Uanis(C116) \\sim Ueq, Uanis(C117) \\sim Ueq, Uanis(C64)
\\sim Ueq, Uanis(C66) \\sim Ueq, Uanis(C157) \\sim Ueq, Uanis(C139) \\sim Ueq,
Uanis(C13) \\sim Ueq: with sigma of 0.02 and sigma for terminal atoms of 0.04
Uanis(I4) = Uanis(I4B)
4. Others
 Sof(I4B)=1-FVAR(1)
 Sof(I4)=FVAR(1)
 Fixed Uiso: C83(0.18) C132(0.13) C133(0.15) C134(0.18) C14(0.16) C15(0.19)
5.a Riding coordinates:
 C66(H66A,H66B,H66C)
5.b Ternary CH refined with riding coordinates:
 C77(H77), C94(H94), C111(H111), C128(H128), C9(H9), C26(H26), C43(H43),
 C60(H60)
5.c Secondary CH2 refined with riding coordinates:
 C78(H78A,H78B), C79(H79A,H79B), C80(H80A,H80B), C81(H81A,H81B), C82(H82A,
 H82B), C84(H84A,H84B), C85(H85A,H85B), C95(H95A,H95B), C96(H96A,H96B),
 C97(H97A,H97B), C98(H98A,H98B), C99(H99A,H99B), C101(H10F,H10G), C102(H10H,
 H10I), C112(H11C,H11D), C113(H11E,H11F), C114(H11G,H11H), C115(H11I,H11J),
 C116(H11K,H11L), C118(H11P,H11Q), C119(H11R,H11S), C129(H12C,H12D), C130(H13C,
 H13D), C131(H13E,H13F), C132(H13G,H13H), C133(H13I,H13J), C135(H13N,H13O),
 C136(H13P,H13Q), C10(H10A,H10B), C11(H11A,H11B), C12(H12A,H12B), C13(H13A,
 H13B), C14(H14A,H14B), C16(H16A,H16B), C17(H17A,H17B), C27(H27A,H27B),
 C28(H28A,H28B), C29(H29A,H29B), C30(H30A,H30B), C31(H31A,H31B), C33(H33A,H33B),
  C34(H34A,H34B), C44(H44A,H44B), C45(H45A,H45B), C46(H46A,H46B), C47(H47A,
 H47B), C48(H48A,H48B), C50(H50A,H50B), C51(H51A,H51B), C61(H61A,H61B),
 C62(H62A,H62B), C63(H63A,H63B), C64(H64A,H64B), C65(H65A,H65B), C67(H67A,H67B),
  C68(H68A,H68B)
5.d Aromatic/amide H refined with riding coordinates:
 C71(H71), C88(H88), C105(H105), C122(H122), C146(H146), C3(H3), C20(H20),
 C37(H37), C54(H54), C155(H155), C140(H140), C149(H149), C152(H152), C143(H143),
  C137(H137)
5.e Idealised Me refined as rotating group:
 C83(H83A,H83B,H83C), C100(H10C,H10D,H10E), C117(H11M,H11N,H11O), C134(H13K,
 H13L,H13M), C147(H14C,H14D,H14E), C148(H14F,H14G,H14H), C15(H15A,H15B,H15C),
 C32(H32A,H32B,H32C), C49(H49A,H49B,H49C), C156(H15D,H15E,H15F), C157(H15G,H15H,
 H15I), C141(H14I,H14J,H14K), C142(H14L,H14M,H14N), C150(H15J,H15K,H15L),
 C151(H15M,H15N,H15O), C153(H15P,H15Q,H15R), C154(H15S,H15T,H15U), C144(H14O,
 H14P,H14Q), C145(H14R,H14S,H14T), C138(H13R,H13S,H13T), C139(H13U,H13V,H13W)
;
_shelx_res_checksum              65487
_olex2_submission_special_instructions 'No special instructions were received'