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_7228807
_publ_section_title
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 Halogen-Bonded Solvates of Tetrahaloethynyl Cavitands
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_journal_name_full               CrystEngComm
_journal_paper_doi               10.1039/C7CE01118K
_journal_year                    2017
_chemical_formula_moiety
'C64 H68 I4 O8, 2.5(C3 H7 N O), C1.5 H5.5 N0.5 O0.5'
_chemical_formula_sum            'C73 H91 I4 N3 O11'
_chemical_formula_weight         1694.08
_space_group_crystal_system      monoclinic
_space_group_IT_number           12
_space_group_name_Hall           '-C 2y'
_space_group_name_H-M_alt        'C 1 2/m 1'
_symmetry_space_group_name_Hall  '-C 2y'
_symmetry_space_group_name_H-M   'C 1 2/m 1'
_atom_sites_solution_hydrogens   mixed
_audit_creation_date             2017-05-19
_audit_creation_method
;
Olex2 1.2
(compiled 2016.11.30 svn.r3356 for OlexSys, GUI svn.r5269)
;
_audit_update_record
;
2017-06-14 deposited with the CCDC.
2017-07-31 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 101.036(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   22.1144(11)
_cell_length_b                   22.3258(17)
_cell_length_c                   17.2116(6)
_cell_measurement_reflns_used    4953
_cell_measurement_temperature    123.00(10)
_cell_measurement_theta_max      61.1780
_cell_measurement_theta_min      3.5790
_cell_volume                     8340.6(8)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_diffrn_ambient_temperature      123.00(10)
_diffrn_measured_fraction_theta_full 0.985
_diffrn_measured_fraction_theta_max 0.985
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0255
_diffrn_reflns_av_unetI/netI     0.0359
_diffrn_reflns_Laue_measured_fraction_full 0.985
_diffrn_reflns_Laue_measured_fraction_max 0.985
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            11003
_diffrn_reflns_point_group_measured_fraction_full 0.985
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_theta_full        59.997
_diffrn_reflns_theta_max         59.997
_diffrn_reflns_theta_min         3.588
_exptl_absorpt_coefficient_mu    12.147
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.62083
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
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    1.349
_exptl_crystal_description       prism
_exptl_crystal_F_000             3400
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.06
_refine_diff_density_max         1.740
_refine_diff_density_min         -1.840
_refine_diff_density_rms         0.145
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     504
_refine_ls_number_reflns         6292
_refine_ls_number_restraints     179
_refine_ls_restrained_S_all      1.051
_refine_ls_R_factor_all          0.1300
_refine_ls_R_factor_gt           0.1010
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1931P)^2^+60.7294P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2903
_refine_ls_wR_factor_ref         0.3324
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4268
_reflns_number_total             6292
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c7ce01118k2.cif
_cod_data_source_block           2_dmf
_cod_database_code               7228807
_shelx_estimated_absorpt_t_max   0.529
_shelx_estimated_absorpt_t_min   0.281
_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
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 C2A-N1 = C3A-N1 = C10-C21 = N2-C39 = N3-C43B = N3-C43 = N3B-C43B = N3B-C44B =
 N3-C44
 1.45 with sigma of 0.01
 C1A-N1
 1.32 with sigma of 0.01
 C1A-O5 = C37-O6
 1.23 with sigma of 0.01
 C19-C20
 1.2 with sigma of 0.01
 C29-C30 = C35-C36 = C29B-C30B
 1.54 with sigma of 0.01
 C33-C34 = C27-C28B = C31-C32 = C32-C33 = C34-C35 = C5-C25 = C26-C27 = C27-C28
 = C28-C29 = C28B-C29B
 1.52 with sigma of 0.01
 N1-O5
 2.3 with sigma of 0.01
 H34A_$1-H28D
 2.2 with sigma of 0.04
 C28-C30 = C26-C28 = C26-C28B = C31-C33 = C27-C29
 2.62 with sigma of 0.01
 H32A-H29C_$1
 2.2 with sigma of 0.04
 H34B-H36C
 2.2 with sigma of 0.04
3. Uiso/Uaniso restraints and constraints
Uanis(C1A) \\sim Ueq, Uanis(C2A) \\sim Ueq, Uanis(O6) \\sim Ueq, Uanis(C37)
\\sim Ueq, Uanis(N2) \\sim Ueq, Uanis(C38) \\sim Ueq, Uanis(C39) \\sim Ueq,
Uanis(N3) \\sim Ueq, Uanis(N3B) \\sim Ueq, Uanis(C42) \\sim Ueq, Uanis(O7)
\\sim Ueq, Uanis(C43B) \\sim Ueq, Uanis(C44B) \\sim Ueq, Uanis(C44) \\sim Ueq,
Uanis(C21) \\sim Ueq, Uanis(C34) \\sim Ueq, Uanis(C28) \\sim Ueq, Uanis(C29)
\\sim Ueq, Uanis(C30) \\sim Ueq, Uanis(C28B) \\sim Ueq, Uanis(C29B) \\sim Ueq,
Uanis(C30B) \\sim Ueq: with sigma of 0.02 and sigma for terminal atoms of 0.04
Uanis(C27) \\sim Ueq, Uanis(C31) \\sim Ueq: with sigma of 0.01 and sigma for
terminal atoms of 0.02
Uanis(C3A) = Uanis(C2A)
Uanis(C44) = Uanis(N3)
Uanis(C43) = Uanis(C43B)
Uanis(C32) = Uanis(C33) = Uanis(C34) = Uanis(C35)
4. Others
 Fixed Sof: H27A(0.6) H27B(0.6) H27C(0.4) H27D(0.4) C28(0.6) H28A(0.6)
 H28B(0.6) C28B(0.4) H28C(0.4) H28D(0.4) C29(0.6) H29A(0.6) H29B(0.6) C29B(0.4)
 H29C(0.4) H29D(0.4) C30(0.6) H30A(0.6) H30B(0.6) H30C(0.6) C30B(0.4) H30D(0.4)
 H30E(0.4) H30F(0.4) H42A(0.5) H42(0.5) C43(0.5) H43A(0.5) H43B(0.5) H43C(0.5)
 C43B(0.5) H43D(0.5) H43E(0.5) H43F(0.5) C44(0.5) H44A(0.5) H44B(0.5) H44C(0.5)
 C44B(0.5) H44D(0.5) H44E(0.5) H44F(0.5) N3(0.5) N3B(0.5) C1A(0.25) H1A(0.25)
 C2A(0.25) H2AA(0.25) H2AB(0.5) H2AC(0.5) C3A(0.25) H3AA(0.25) H3AB(0.5)
 H3AC(0.5) N1(0.25) O5(0.25) C37(0.25) H37(0.25) C38(0.25) H38A(0.25)
 H38B(0.25) H38C(0.25) C39(0.25) H39A(0.25) H39B(0.25) H39C(0.25) N2(0.25)
 O6(0.25)
5.a Riding coordinates:
 C30B(H30D,H30E,H30F), C39(H39A,H39B,H39C)
5.b Ternary CH refined with riding coordinates:
 C5(H5), C12(H12)
5.c Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C18(H18A,H18B), C25(H25A,H25B), C26(H26A,H26B), C27(H27A,
 H27B), C27(H27C,H27D), C28(H28A,H28B), C28B(H28C,H28D), C29(H29A,H29B),
 C29B(H29C,H29D), C31(H31A,H31B), C32(H32A,H32B), C33(H33A,H33B), C34(H34A,
 H34B), C35(H35A,H35B)
5.d Me refined with riding coordinates:
 C30(H30A,H30B,H30C), C2A(H2AA,H2AB,H2AC), C3A(H3AA,H3AB,H3AC)
5.e Aromatic/amide H refined with riding coordinates:
 C1(H1), C7(H7), C14(H14), C42(H42A), C42(H42), C1A(H1A), C37(H37)
5.f Idealised Me refined as rotating group:
 C36(H36A,H36B,H36C), C43(H43A,H43B,H43C), C43B(H43D,H43E,H43F), C44(H44A,H44B,
 H44C), C44B(H44D,H44E,H44F), C38(H38A,H38B,H38C)
;
_shelx_res_checksum              26958
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'