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_7228806
_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 H6 O)'
_chemical_formula_sum            'C78.5 H97 I4 O11.5'
_chemical_formula_weight         1732.16
_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             2017-07-05
_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                114.995(5)
_cell_angle_beta                 91.376(6)
_cell_angle_gamma                116.803(6)
_cell_formula_units_Z            2
_cell_length_a                   16.4002(10)
_cell_length_b                   17.5718(8)
_cell_length_c                   19.1603(10)
_cell_measurement_reflns_used    7976
_cell_measurement_temperature    123.00(10)
_cell_measurement_theta_max      72.5820
_cell_measurement_theta_min      4.5450
_cell_volume                     4306.9(6)
_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 0.998
_diffrn_measured_fraction_theta_max 0.962
_diffrn_measurement_details
;
  1 omega  -41.00   33.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.4013   37.0000   30.0000 74

  2 omega  -14.00   30.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.4013   37.0000 -180.0000 44

  3 omega  -97.00  -69.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.4013  -77.0000  -60.0000 28

  4 omega -120.00   -2.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.4013  -19.0000 -150.0000 118

  5 omega  -39.00   -9.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.4013  -77.0000  -60.0000 30

  6 omega  -95.00   -5.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.4013  125.0000   60.0000 90

  7 omega   44.00   74.00   1.0000    5.0000
omega____ theta____ kappa____ phi______ frames
    -       41.4013 -137.0000  -67.0000 30

  8 omega   34.00   79.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      105.0818  -30.0000 -180.0000 45

  9 omega   40.00   73.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      105.0818  -45.0000   90.0000 33

 10 omega  130.00  159.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      105.0818  137.0000   -4.0000 29

 11 omega   50.00  105.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      105.0818  -94.0000  120.0000 55

 12 omega   37.00   91.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      105.0818  -30.0000  120.0000 54

 13 omega   36.00  120.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      105.0818 -125.0000  -30.0000 84

 14 omega   80.00  160.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      105.0818   30.0000   30.0000 80

 15 omega   46.00   89.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      105.0818  -30.0000   30.0000 43

 16 omega   45.00  103.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      105.0818  -94.0000 -180.0000 58

 17 omega   91.00  120.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      105.0818 -125.0000  120.0000 29

 18 omega   96.00  178.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      105.0818   30.0000   90.0000 82

 19 omega   29.00   66.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      105.0818  -30.0000  -90.0000 37

 20 omega   43.00   88.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      105.0818  -30.0000  -30.0000 45

 21 omega  133.00  178.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      105.0818   45.0000  -60.0000 45

 22 omega   37.00  135.00   1.0000   60.0000
omega____ theta____ kappa____ phi______ frames
    -      105.0818  -77.0000  -30.0000 98
;
_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      -0.0884608000
_diffrn_orient_matrix_UB_12      -0.0686522000
_diffrn_orient_matrix_UB_13      0.0148758000
_diffrn_orient_matrix_UB_21      0.0639128000
_diffrn_orient_matrix_UB_22      0.0053425000
_diffrn_orient_matrix_UB_23      0.0642216000
_diffrn_orient_matrix_UB_31      -0.0019518000
_diffrn_orient_matrix_UB_32      0.0887968000
_diffrn_orient_matrix_UB_33      0.0641836000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0603
_diffrn_reflns_av_unetI/netI     0.0866
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            30875
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.962
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.443
_diffrn_reflns_theta_min         3.015
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    11.768
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.29053
_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    1.336
_exptl_crystal_description       block
_exptl_crystal_F_000             1744
_exptl_crystal_size_max          0.3525
_exptl_crystal_size_mid          0.2939
_exptl_crystal_size_min          0.2464
_refine_diff_density_max         5.437
_refine_diff_density_min         -2.267
_refine_diff_density_rms         0.232
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     904
_refine_ls_number_reflns         16680
_refine_ls_number_restraints     565
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.2671
_refine_ls_R_factor_gt           0.2203
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1924P)^2^+181.5318P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.4934
_refine_ls_wR_factor_ref         0.5261
_reflns_Friedel_coverage         0.000
_reflns_number_gt                10948
_reflns_number_total             16680
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ce01118k2.cif
_cod_data_source_block           3_acetone
_cod_original_cell_volume        4306.9(5)
_cod_original_formula_sum        'C78.50 H97 I4 O11.50'
_cod_database_code               7228806
_shelx_shelxl_version_number     2014/7
_chemical_oxdiff_formula         'C90 H100 N4 I4 O4'
_reflns_odcompleteness_completeness 99.89
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.49
_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
 C81-O13
 1.2 with sigma of 0.02
 C82-C81 = C83-C81
 1.5 with sigma of 0.02
 C83-C82
 2.5 with sigma of 0.02
 C16-C17 = C16-C15 = C15-C14 = C68-C67 = C67-C66 = C66-C65 = C65-C64 = C64-C63
 = C14-C13 = C34-C33 = C33-C32 = C32-C31 = C31-C30 = C30-C29 = C51-C50 = C50-
 C49 = C49-C48 = C48-C47 = C47-C46 = C13-C12
 1.52 with sigma of 0.01
 H76C-H80C_$1 = H74B-H82B
 2.1 with sigma of 0.02
 C58B-C59B \\sim C59-C58
 with sigma of 0.01
 I4B-C59B \\sim I4-C59
 with sigma of 0.01
 C58-C59 \\sim C7-C8
 with sigma of 0.02
 C59-I4 \\sim C8-I1
 with sigma of 0.02
 C82-O13 \\sim O13-C83
 with sigma of 0.02
 C79-C78 \\sim C80-C78 \\sim C73-C72 \\sim C74-C72 \\sim C70-C69 \\sim C71-C69
\\sim C77-C75 \\sim C76-C75
 \\sim C82-C81 \\sim C83-C81
 with sigma of 0.02
 C58B-C53B \\sim C58-C53
 with sigma of 0.01
 C54-C53B \\sim C53B-C52 \\sim C54-C53 \\sim C53-C52
 with sigma of 0.01
 C53-C58 \\sim C2-C7
 with sigma of 0.02
3. Restrained planarity
 O13, C81, C82, C83
 with sigma of 0.1
4. Uiso/Uaniso restraints and constraints
Uanis(C15) \\sim Ueq, Uanis(C13) \\sim Ueq, Uanis(C48) \\sim Ueq, Uanis(C3)
\\sim Ueq, Uanis(C73) \\sim Ueq, Uanis(C21) \\sim Ueq, Uanis(C22) \\sim Ueq,
Uanis(C23) \\sim Ueq, Uanis(C35) \\sim Ueq, Uanis(C55) \\sim Ueq, Uanis(C58)
\\sim Ueq, Uanis(C18) \\sim Ueq, Uanis(C19) \\sim Ueq, Uanis(C10) \\sim Ueq,
Uanis(I1) \\sim Ueq: with sigma of 0.005 and sigma for terminal atoms of 0.01
Uanis(C47) \\sim Ueq, Uanis(C31) \\sim Ueq, Uanis(C63) \\sim Ueq, Uanis(C65)
\\sim Ueq, Uanis(C14) \\sim Ueq, Uanis(C37) \\sim Ueq, Uanis(C35) \\sim Ueq,
Uanis(C18) \\sim Ueq, Uanis(C7) \\sim Ueq, Uanis(C8) \\sim Ueq, Uanis(C59)
\\sim Ueq, Uanis(C53) \\sim Ueq, Uanis(C2) \\sim Ueq, Uanis(C45) \\sim Ueq,
Uanis(C82) \\sim Ueq, Uanis(O13) \\sim Ueq, Uanis(C81) \\sim Ueq, Uanis(C83)
\\sim Ueq, Uanis(C77) \\sim Ueq, Uanis(C75) \\sim Ueq, Uanis(C76) \\sim Ueq,
Uanis(C74) \\sim Ueq, Uanis(O8) \\sim Ueq, Uanis(O10) \\sim Ueq, Uanis(C71)
\\sim Ueq, Uanis(O9) \\sim Ueq, Uanis(C70) \\sim Ueq, Uanis(C69) \\sim Ueq,
Uanis(I4) \\sim Ueq, Uanis(C25) \\sim Ueq, Uanis(C50) \\sim Ueq, Uanis(C49)
\\sim Ueq, Uanis(C51) \\sim Ueq, Uanis(C46) \\sim Ueq, Uanis(C30) \\sim Ueq,
Uanis(C61) \\sim Ueq, Uanis(C66) \\sim Ueq, Uanis(C68) \\sim Ueq, Uanis(C80)
\\sim Ueq, Uanis(C60) \\sim Ueq, Uanis(O7) \\sim Ueq, Uanis(C40) \\sim Ueq,
Uanis(C27) \\sim Ueq, Uanis(O4) \\sim Ueq, Uanis(C67) \\sim Ueq, Uanis(C11)
\\sim Ueq, Uanis(C12) \\sim Ueq, Uanis(O5) \\sim Ueq, Uanis(C10) \\sim Ueq,
Uanis(C79) \\sim Ueq, Uanis(C24) \\sim Ueq, Uanis(C1) \\sim Ueq, Uanis(C54)
\\sim Ueq, Uanis(C64) \\sim Ueq, Uanis(C38) \\sim Ueq, Uanis(C39) \\sim Ueq,
Uanis(C62) \\sim Ueq, Uanis(C57) \\sim Ueq, Uanis(C4) \\sim Ueq, Uanis(C36)
\\sim Ueq, Uanis(C44) \\sim Ueq, Uanis(C20) \\sim Ueq, Uanis(C6) \\sim Ueq,
Uanis(C5) \\sim Ueq, Uanis(C29) \\sim Ueq, Uanis(C72) \\sim Ueq, Uanis(C52)
\\sim Ueq, Uanis(O3) \\sim Ueq: with sigma of 0.01 and sigma for terminal atoms
of 0.02
Uanis(I2) = Uanis(I2B)
Uanis(C59) = Uanis(C59B)
Uanis(C58) = Uanis(C58B)
Uanis(C53B) = Uanis(C53)
5. Others
 Fixed Sof: I2(0.9) I4(0.66667) C53(0.66667) C58(0.66667) C59(0.66667)
 C79(0.5) H79A(0.5) H79B(0.5) H79C(0.5) C78(0.5) O12(0.5) C80(0.5) H80A(0.5)
 H80B(0.5) H80C(0.5) O11(0.5) C75(0.5) C76(0.5) H76A(0.5) H76B(0.5) H76C(0.5)
 C77(0.5) H77A(0.5) H77B(0.5) H77C(0.5) I4B(0.33333) I2B(0.1) C58B(0.33333)
 C59B(0.33333) C53B(0.33333) O13(0.5) C81(0.5) C82(0.5) H82A(0.5) H82B(0.5)
 H82C(0.5) C83(0.5) H83A(0.5) H83B(0.5) H83C(0.5)
 Fixed Uiso: C16(0.19) C17(0.2) C32(0.16) C33(0.18) C34(0.2)
6.a Riding coordinates:
 C34(H34A,H34B,H34C), C82(H82A,H82B,H82C)
6.b Ternary CH refined with riding coordinates:
 C11(H11), C28(H28), C45(H45), C62(H62)
6.c Secondary CH2 refined with riding coordinates:
 C16(H16A,H16B), C9(H9A,H9B), C10(H10A,H10B), C12(H12A,H12B), C13(H13A,H13B),
 C14(H14A,H14B), C15(H15A,H15B), C26(H26A,H26B), C27(H27A,H27B), C29(H29A,H29B),
  C30(H30A,H30B), C31(H31A,H31B), C32(H32A,H32B), C33(H33A,H33B), C43(H43A,
 H43B), C44(H44A,H44B), C46(H46A,H46B), C47(H47A,H47B), C48(H48A,H48B),
 C49(H49A,H49B), C50(H50A,H50B), C60(H60A,H60B), C61(H61A,H61B), C63(H63A,H63B),
  C64(H64A,H64B), C65(H65A,H65B), C66(H66A,H66B), C67(H67A,H67B)
6.d Aromatic/amide H refined with riding coordinates:
 C5(H5), C22(H22), C39(H39), C56(H56)
6.e Idealised Me refined as rotating group:
 C17(H17A,H17B,H17C), C51(H51A,H51B,H51C), C68(H68A,H68B,H68C), C79(H79A,H79B,
 H79C), C80(H80A,H80B,H80C), C73(H73A,H73B,H73C), C74(H74A,H74B,H74C), C76(H76A,
 H76B,H76C), C77(H77A,H77B,H77C), C70(H70A,H70B,H70C), C71(H71A,H71B,H71C),
 C83(H83A,H83B,H83C)
;
_shelx_res_checksum              88110
_olex2_submission_special_instructions 'No special instructions were received'