Solid-state isolation of a unique, small-molecule, supra-heterodimer of large hexameric assemblies of C-methylcalix[4]resorcinarene
Oliver, Clive L.; Báthori, Nikoletta B.; Jackson, Graham E.; Kuter, David; Cruickshank, Dyanne L.; CrystEngComm 18 (2016) 3015–; doi:10.1039/C6CE00698A

data_7224810
_publ_section_title
;
 Solid-state isolation of a unique, small-molecule, supra-heterodimer of
 large hexameric assemblies of C-methylcalix[4]resorcinarene
;
_journal_issue                   17
_journal_name_full               CrystEngComm
_journal_page_first              3015
_journal_paper_doi               10.1039/C6CE00698A
_journal_volume                  18
_journal_year                    2016
_chemical_formula_moiety
'0.25(C32 H31 O8), 0.75(C32 H32 O8), 0.49(C4 H10 O1), 1.42(O), 0.39(C4 H9 O)'
_chemical_formula_sum            'C35.54 H40.21 O10.3'
_chemical_formula_weight         632.17
_space_group_crystal_system      trigonal
_space_group_IT_number           161
_space_group_name_Hall           'R 3 -2"c'
_space_group_name_H-M_alt        'R 3 c :H'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_audit_creation_date             2016-03-29
_audit_creation_method
;
Olex2 1.2
(compiled 2016.02.19 svn.r3266 for OlexSys, GUI svn.r5155)
;
_audit_update_record
;
2016-03-29 deposited with the CCDC.
2016-04-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_formula_units_Z            72
_cell_length_a                   29.9017(19)
_cell_length_b                   29.9017(19)
_cell_length_c                   96.281(6)
_cell_measurement_reflns_used    9870
_cell_measurement_temperature    100
_cell_measurement_theta_max      28.62
_cell_measurement_theta_min      2.31
_cell_volume                     74553(8)
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Bruker ApexII Duo'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0438
_diffrn_reflns_av_unetI/netI     0.0514
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -39
_diffrn_reflns_limit_k_max       39
_diffrn_reflns_limit_k_min       -38
_diffrn_reflns_limit_l_max       122
_diffrn_reflns_limit_l_min       -128
_diffrn_reflns_number            114453
_diffrn_reflns_point_group_measured_fraction_full 0.941
_diffrn_reflns_point_group_measured_fraction_max 0.916
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         28.282
_diffrn_reflns_theta_min         1.786
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.6786
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0476 before and 0.0419 after correction.
The Ratio of minimum to maximum transmission is 0.9097.
The \l/2 correction factor is 0.00150.
;
_exptl_crystal_colour            'clear brownish brown'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   brownish
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.014
_exptl_crystal_description       block
_exptl_crystal_F_000             24181
_exptl_crystal_size_max          0.47
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.24
_refine_diff_density_max         0.813
_refine_diff_density_min         -0.333
_refine_diff_density_rms         0.053
_refine_ls_abs_structure_details
;
 Flack x determined using 10243 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.20(19)
_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     1748
_refine_ls_number_reflns         37710
_refine_ls_number_restraints     1383
_refine_ls_restrained_S_all      1.033
_refine_ls_R_factor_all          0.0846
_refine_ls_R_factor_gt           0.0577
_refine_ls_shift/su_max          0.138
_refine_ls_shift/su_mean         0.002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1009P)^2^+8.0670P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1501
_refine_ls_wR_factor_ref         0.1653
_reflns_Friedel_coverage         0.832
_reflns_Friedel_fraction_full    0.883
_reflns_Friedel_fraction_max     0.832
_reflns_number_gt                27783
_reflns_number_total             37710
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            c6ce00698a2.cif
_cod_data_source_block           nocut_sq
_cod_depositor_comments          'Adding full bibliography for 7224810.cif.'
_cod_original_cell_volume        74553(11)
_cod_original_formula_sum        'C35.54 H40.21 O10.30'
_cod_database_code               7224810
_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, All O(H) groups
2. Restrained distances
 O1H-O9W
 2.7 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
All non-hydrogen atoms have similar U: within 1.7A with sigma of 0.04 and sigma
for terminal atoms of 0.08
4. Rigid body (RIGU) restrains
 C3FB, O1FB, C1FB, C2FB, C4FB
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C4F, O1F, C1F, C2F, C3F
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 C4H, O1H, C1H, C2H, C3H
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Same fragment restrains
{O1E, C1E, C2E, C3E, C4E} sigma for 1-2: 0.02, 1-3: 0.04
as
{O1G, C1G, C2G, C3G, C4G}
{O1E, C1E, C2E, C3E, C4E} sigma for 1-2: 0.02, 1-3: 0.04
as
{O1F, C1F, C2F, C3F, C4F}
{O1E, C1E, C2E, C3E, C4E} sigma for 1-2: 0.02, 1-3: 0.04
as
{O1FB, C1FB, C2FB, C3FB, C4FB}
{O1E, C1E, C2E, C3E, C4E} sigma for 1-2: 0.02, 1-3: 0.04
as
{O1H, C1H, C2H, C3H, C4H}
6. Others
 Sof(O1G)=Sof(H1G)=Sof(C1G)=Sof(H1GA)=Sof(H1GB)=Sof(C2G)=Sof(H2GA)=Sof(H2GB)=
 Sof(C3G)=Sof(H3GA)=Sof(H3GB)=Sof(C4G)=Sof(H4GA)=Sof(H4GB)=Sof(H4GC)=FVAR(1)
 Sof(O1FB)=Sof(C1FB)=Sof(H1FC)=Sof(H1FD)=Sof(C2FB)=Sof(H2FC)=Sof(H2FD)=
 Sof(C3FB)=Sof(H3FC)=Sof(H3FD)=Sof(C4FB)=Sof(H4FD)=Sof(H4FE)=Sof(H4FF)=1-FVAR(2)
 Sof(O1F)=Sof(H1F)=Sof(C1F)=Sof(H1FA)=Sof(H1FB)=Sof(C2F)=Sof(H2FA)=Sof(H2FB)=
 Sof(C3F)=Sof(H3FA)=Sof(H3FB)=Sof(C4F)=Sof(H4FA)=Sof(H4FB)=Sof(H4FC)=FVAR(2)
 Sof(O7WB)=0.33333*(1-FVAR(4))
 Sof(O7WA)=0.33333*FVAR(4)
7.a Ternary CH refined with riding coordinates:
 C7A(H7A), C15A(H15A), C23A(H23A), C31A(H31A), C7D(H7D), C15D(H15D),
 C23D(H23D), C31D(H31D), C7B(H7B), C15B(H15B), C23B(H23B), C31B(H31B), C7C(H7C),
  C15C(H15C), C23C(H23C), C31C(H31C)
7.b Secondary CH2 refined with riding coordinates:
 C1G(H1GA,H1GB), C2G(H2GA,H2GB), C3G(H3GA,H3GB), C1E(H1EA,H1EB), C2E(H2EA,
 H2EB), C3E(H3EA,H3EB), C1F(H1FA,H1FB), C2F(H2FA,H2FB), C3F(H3FA,H3FB),
 C1FB(H1FC,H1FD), C2FB(H2FC,H2FD), C3FB(H3FC,H3FD), C1H(H1HA,H1HB), C2H(H2HA,
 H2HB), C3H(H3HA,H3HB)
7.c Aromatic/amide H refined with riding coordinates:
 C6A(H6A), C11A(H11A), C14A(H14A), C19A(H19A), C22A(H22A), C27A(H27A),
 C30A(H30A), C3D(H3D), C6D(H6D), C11D(H11D), C14D(H14D), C19D(H19D), C22D(H22D),
  C27D(H27D), C30D(H30D), C3B(H3B), C6B(H6B), C11B(H11B), C14B(H14B),
 C19B(H19B), C22B(H22B), C27B(H27B), C30B(H30B), C3C(H3C), C6C(H6C), C11C(H11C),
  C14C(H14C), C19C(H19C), C22C(H22C), C27C(H27C), C30C(H30C)
7.d Tetrahedral OH refined with riding coordinates:
 O2A(H2A), O4A(H4A), O10A(H10A), O12A(H12A), O18A(H18A), O20A(H20A),
 O26A(H26A), O28A(H28A), O2D(H2D), O4D(H4D), O10D(H10D), O12D(H12D), O18D(H18D),
  O20D(H20D), O26D(H26D), O28D(H28D), O4B(H4B), O10B(H10B), O12B(H12B),
 O18B(H18B), O20B(H20B), O26B(H26B), O28B(H28B), O2C(H2C), O4C(H4C), O10C(H10C),
  O20C(H20C), O26C(H26C), O28C(H28C), O1G(H1G), O1E(H1E)
7.e Idealised Me refined as rotating group:
 C8A(H8AA,H8AB,H8AC), C16A(H16J,H16K,H16L), C24A(H24J,H24K,H24L), C32A(H32J,
 H32K,H32L), C8D(H8DA,H8DB,H8DC), C16D(H16A,H16B,H16C), C24D(H24A,H24B,H24C),
 C32D(H32A,H32B,H32C), C8B(H8BA,H8BB,H8BC), C16B(H16D,H16E,H16F), C24B(H24D,
 H24E,H24F), C32B(H32D,H32E,H32F), C8C(H8CA,H8CB,H8CC), C16C(H16G,H16H,H16I),
 C24C(H24G,H24H,H24I), C32C(H32G,H32H,H32I), C4G(H4GA,H4GB,H4GC), C4E(H4EA,H4EB,
 H4EC), C4F(H4FA,H4FB,H4FC), C4FB(H4FD,H4FE,H4FF), C4H(H4HA,H4HB,H4HC)
7.f Idealised tetrahedral OH refined as rotating group:
 O2B(H2B), O12C(H12C), O18C(H18C), O1F(H1F)
;
_shelx_res_checksum              39967
_shelx_fab_checksum              38802
_shelx_shelxl_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'