A facile and efficient preparation of prism[6]arene and its dual responsive complexation with 1-adamantane ammonium tetrakis[3,5-bis(trifluoromethyl)-phenyl]borate
Zhang, Guojiao; Li, Zhengxiang; Pan, Zhen; Zhao, Dezhi; Han, Chengyou; New Journal of Chemistry 47 (2023) 18910–18913; doi:10.1039/D3NJ03586G

data_7062784
_publ_section_title
;
 A facile and efficient preparation of prism[6]arene and its dual
 responsive complexation with 1-adamantane ammonium
 tetrakis[3,5-bis(trifluoromethyl)-phenyl]borate
;
_journal_issue                   41
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              18910
_journal_page_last               18913
_journal_paper_doi               10.1039/D3NJ03586G
_journal_volume                  47
_journal_year                    2023
_chemical_formula_moiety
'C90 H96 O12, 1[CH2Cl2], 2[CH4O], 1[CH4O], 1[CH4O]'
_chemical_formula_sum            'C95 H114 Cl2 O16'
_chemical_formula_weight         1582.76
_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     dual
_audit_creation_date             2023-10-02
_audit_creation_method
;
Olex2 1.5-dev
(compiled 2023.09.29 svn.re1ec1418 for OlexSys, GUI svn.r6697)
;
_audit_update_record
;
2023-10-04 deposited with the CCDC.	2023-10-05 downloaded from the CCDC.
;
_cell_angle_alpha                96.965(6)
_cell_angle_beta                 91.065(5)
_cell_angle_gamma                95.046(6)
_cell_formula_units_Z            4
_cell_length_a                   19.6087(18)
_cell_length_b                   19.598(2)
_cell_length_c                   21.824(2)
_cell_measurement_reflns_used    9863
_cell_measurement_temperature    225.0
_cell_measurement_theta_max      54.01
_cell_measurement_theta_min      2.49
_cell_volume                     8289.0(14)
_computing_cell_refinement       'SAINT V8.40B (Bruker, 2019)'
_computing_data_collection       'APEX4 V2022.1-1 (Bruker, 2022)'
_computing_data_reduction        'SAINT V8.40B (Bruker, 2019)'
_computing_molecular_graphics    'Olex2 1.5-dev (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-dev (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      225.00
_diffrn_detector_area_resol_mean 7.41
_diffrn_detector_type            'Bruker PHOTON II'
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 VENTURE Metaljet PHOTON II'
_diffrn_measurement_method       '\w and \f shutterless scans'
_diffrn_measurement_specimen_support 'nylon loop'
_diffrn_radiation_type           GaK\a
_diffrn_radiation_wavelength     1.34139
_diffrn_reflns_av_R_equivalents  0.0846
_diffrn_reflns_av_unetI/netI     0.1320
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            62870
_diffrn_reflns_point_group_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        45.000
_diffrn_reflns_theta_max         45.000
_diffrn_reflns_theta_min         1.775
_exptl_absorpt_coefficient_mu    0.809
_exptl_absorpt_correction_T_max  0.3666
_exptl_absorpt_correction_T_min  0.2106
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.1327 before and 0.0672 after correction.
The Ratio of minimum to maximum transmission is 0.5745.
The \l/2 correction factor is Not present.
;
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.268
_exptl_crystal_description       block
_exptl_crystal_F_000             3384
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.535
_refine_diff_density_min         -0.527
_refine_diff_density_rms         0.068
_refine_ls_extinction_coef       0.00029(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     1920
_refine_ls_number_reflns         20095
_refine_ls_number_restraints     1801
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.2067
_refine_ls_R_factor_gt           0.1071
_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^)+(0.1584P)^2^+19.1583P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2846
_refine_ls_wR_factor_ref         0.3527
_reflns_Friedel_coverage         0.000
_reflns_number_gt                10875
_reflns_number_total             20095
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d3nj03586g2.cif
_cod_data_source_block           20221011_cjq_songyang_0m
_cod_depositor_comments          'Adding full bibliography for 7062784.cif.'
_cod_original_cell_volume        8289.1(14)
_cod_database_code               7062784
_shelx_shelxl_version_number     2018/3
_shelx_estimated_absorpt_t_max   0.923
_shelx_estimated_absorpt_t_min   0.902
_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
 O00Q-C033 \\sim O00R-C033
 with sigma of 0.02
 O00Q-C05S \\sim O00R-C1
 with sigma of 0.02
 C05S-C53 \\sim C1-C53A
 with sigma of 0.02
 O00Q-C53 \\sim O00R-C53A
 with sigma of 0.04
 C033-C05S \\sim C033-C1
 with sigma of 0.04
 O02Z-C04V \\sim O0-C04V
 with sigma of 0.02
 O02Z-C20 \\sim O0-C20A
 with sigma of 0.02
 C17-C20 \\sim C17A-C20A
 with sigma of 0.02
 O02Z-C17 \\sim O0-C17A
 with sigma of 0.04
 C04V-C20 \\sim C04V-C20A
 with sigma of 0.04
 O00R-C1 \\sim O0-C20A
 with sigma of 0.001
 C20A-C17A \\sim C53A-C1
 with sigma of 0.001
 C53A-O00R \\sim O0-C17A
 with sigma of 0.001
3. Uiso/Uaniso restraints and constraints
O00Q \\sim C05S \\sim C53 \\sim O00R \\sim C1 \\sim C53A \\sim O02Z \\sim C20
\\sim C20A \\sim O0 \\sim C17 \\sim C17A: within 2A with sigma of 0.001 and
sigma for terminal atoms of 0.002 within 2A
4. Rigid body (RIGU) restrains
 C00X, O003, C02I, C05E, C01H, C02C, C04Y, C00S, C02D, C02S, C011, C01I, C010,
 C02R, C01T, C013, C019, C03L, C01M, O00A, C034, C01F, C048, O00N, C04K, C02P,
 C01N, C038, C03G, C03P, C04B, C04U, C00V, C027, O00L, C040, C03D, C044, C04M,
 O008, C01J, C057, C04P, C04I, C03R, C047, C01P, C01Z, C05Y, C043, C049, C04W,
 O007, C041, C023, C03T, C03N, O00D, C04S, C03Z, C032, C04H, C04V, C02A, C054,
 C05I, C033, C03Y, O02Z, C05C, C03E, C03U, C05H, O00Q, C03M, C20, C04A, C03F,
 C04F, C05S, C035, C04G, C17, C04Q, C05A, C53, C02U, C046, O00P, C04J, O00H,
 C045, C03A, C04E, C04X, C05J, C042, C05O, C05M, O00T, C05W, C05U
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
 C058, O002, C026, C05G, C01C, C03C, C059, C01B, C036, C02F, C017, C01D, C01S,
 C025, C02E, C01Q, C03Q, C02O, C039, C020, C02N, C02L, O00G, O00I, C03J, C028,
 C03O, C02X, C05D, C04Z, C01E, C01K, C02B, C02G, C05V, C05L, C016, C03B, O00J,
 C02M, O00E, C01L, C01A, C01Y, C02H, C04R, C055, C01G, C03K, C02Y, C03W, C04O,
 C05R, O00O, C015, C02W, C037, C02Q, O00K, C04T, C030, C04D, C00U, C031, C00Z,
 C051, C056, C02J, C03I, O004, C012, C022, C02V, C061, O00F, C00Y, C05T, C01R,
 C03S, C01W, C050, C014, C03H, C05P, C021, C02T, C05B, O005, C04C, C02K, C01V,
 O00M, C01X, C03X, C024, C03V, C052, C029, C04N, O00C, C05F, C053
 with sigma for 1-2 distances of 0.001 and sigma for 1-3 distances of 0.001
5. Others
 Sof(O00R)=Sof(C1)=Sof(H1A)=Sof(H1B)=Sof(C53A)=Sof(H53D)=Sof(H53E)=Sof(H53F)=1-
 FVAR(1)
 Sof(O00Q)=Sof(C05S)=Sof(H05X)=Sof(H05Y)=Sof(C53)=Sof(H53A)=Sof(H53B)=
 Sof(H53C)=FVAR(1)
 Sof(O0)=Sof(C17A)=Sof(H17D)=Sof(H17E)=Sof(H17F)=Sof(C20A)=Sof(H20C)=Sof(H20D)=
 1-FVAR(2)
 Sof(O02Z)=Sof(C17)=Sof(H17A)=Sof(H17B)=Sof(H17C)=Sof(C20)=Sof(H20A)=Sof(H20B)=
 FVAR(2)
6.a Secondary CH2 refined with riding coordinates:
 C027(H02A,H02B), C02D(H02D,H02E), C02G(H02H,H02I), C02T(H02K,H02O), C02Y(H02Q,
 H02R), C036(H03H,H03I), C039(H03J,H03K), C03I(H03N,H03O), C03L(H03B,H03C),
 C03X(H03Q,H03U), C03Y(H03D,H03G), C043(H04A,H04B), C047(H04C,H04D), C04B(H04F,
 H04G), C04K(H04K,H04L), C04R(H5,HD), C04S(H04Q,H04R), C04T(H6,HE), C04X(H04Y,
 HF), C04Z(H7,HI), C050(H8,HJ), C051(H9,HK), C052(H10,HL), C054(H05A,H05B),
 C055(H12,HO), C057(H05C,H05D), C05A(H05E,H05F), C05D(H17,HX), C05E(H05H,H05I),
 C05F(H18,HY), C05G(H19,HZ), C05J(H05P,H05Q), C05S(H05X,H05Y), C05T(H23,H31),
 C05W(H05,H36), C20(H20A,H20B), C1(H1A,H1B), C20A(H20C,H20D)
6.b Aromatic/amide H refined with riding coordinates:
 C012(H012), C015(H015), C01D(H01D), C01F(H01F), C01I(H01I), C01R(H01R),
 C01T(H01T), C01V(H01V), C01Y(H01Y), C022(H022), C024(H024), C02C(H02C),
 C02E(H02F), C02F(H02G), C02H(H02J), C02L(H02L), C02M(H02M), C02N(H02N),
 C02P(H02P), C02S(H02S), C02W(H02W), C02X(H02X), C030(H030), C034(H034),
 C038(H038), C03A(H03A), C03B(H03L), C03C(H03M), C03E(H03E), C03F(H03F),
 C03O(H03P), C03R(H03R), C03S(H03S), C03T(H03T), C03V(H03V), C03Z(H03Z),
 C040(H040), C041(H041), C044(H044), C046(H046), C04A(H04E), C04C(H04),
 C04D(H2), C04E(H04H), C04H(H04I), C04J(H04J), C04P(H04P), C05C(H05G)
6.c Idealised Me refined as rotating group:
 C04M(H04M,H04N,H04O), C04N(H3,H,HA), C04O(H4,HB,HC), C04U(H04S,H04T,H04U),
 C04W(H04V,H04W,H04X), C04Y(H04Z,HG,HH), C053(H11,HM,HN), C056(H13,HP,HQ),
 C058(H14,HR,HS), C059(H15,HT,HU), C05B(H16,HV,HW), C05H(H05J,H05K,H05L),
 C05I(H05M,H05N,H05O), C05L(H20,H25,H26), C05M(H05R,H05S,H05T), C05O(H05U,H05V,
 H05W), C05P(H21,H27,H28), C05R(H22,H29,H30), C05U(H05Z,H32,H33), C05V(H24,H34,
 H35), C05Y(H1,H37,H38), C061(H06A,H06B,H06C), C17(H17A,H17B,H17C), C53(H53A,
 H53B,H53C), C53A(H53D,H53E,H53F), C17A(H17D,H17E,H17F)
;
_smtbx_masks_special_details
;
A solvent mask was calculated and 468 electrons were 
found in a volume of 1508\%A^3^ in 3 voids per unit cell. 
This is consistent with the presence of 1[CH2Cl2], 2[CH4O] in
one void and two more methanol molecules in two more voids per
formula unit, which account for 456 electrons per unit cell.

This is consistent with the crysallisation conditions.
;
_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 1.2
_shelx_res_checksum              25698
_shelx_fab_checksum              59342
_olex2_submission_special_instructions 'No special instructions were received'