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#$Date: 2025-08-19 22:06:29 +0200 (Tue 19 de Aug de 2025) $
#$Revision: 301812 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/13/4021387.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_4021387
loop_
_publ_author_name
'Bernardo Masci'
'Stefano Levi Mortera'
'Daniela Persiani'
'Pierre Thuéry'
_publ_contact_author             'P. Thuéry'
_publ_contact_author_address
;
      CEA/Saclay, SCM (CNRS URA 331)
      Bât. 125
      91191 Gif-sur-Yvette
      France
;
_publ_contact_author_email       thuery@drecam.cea.fr
_publ_contact_author_fax         '33 1 69 08 66 40'
_publ_contact_author_phone       '33 01 69 08 63 29'
_publ_section_title
;
 Methyl Ether Derivatives of p-tert-Butyl[3.1.3.1]homooxacalixarene.
 Formation, Structure, and Complexes with
 Quaternary Ammonium Ions
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              504
_journal_page_last               511
_journal_paper_doi               10.1021/jo051922t
_journal_volume                  71
_journal_year                    2006
_chemical_formula_sum            'C48 H64 O6'
_chemical_formula_weight         736.99
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                89.214(7)
_cell_angle_beta                 81.669(6)
_cell_angle_gamma                79.155(7)
_cell_formula_units_Z            1
_cell_length_a                   6.0627(7)
_cell_length_b                   11.5013(11)
_cell_length_c                   15.322(2)
_cell_measurement_reflns_used    7838
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.68
_cell_measurement_theta_min      3.22
_cell_volume                     1038.1(2)
_computing_cell_refinement       'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_data_collection       'Kappa-CCD software (Nonius B.V., 1998)'
_computing_data_reduction        'DENZO-SMN (Otwinowski & Minor, 1997)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 1999)'
_computing_publication_material  'SHELXTL (Sheldrick, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.914
_diffrn_measured_fraction_theta_max 0.914
_diffrn_measurement_device_type  'Nonius Kappa-CCD'
_diffrn_measurement_method       'φ scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0580
_diffrn_reflns_av_sigmaI/netI    0.0703
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            7838
_diffrn_reflns_theta_full        25.68
_diffrn_reflns_theta_max         25.68
_diffrn_reflns_theta_min         3.22
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  0
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.179
_exptl_crystal_density_meas      ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             400
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.336
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.051
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     251
_refine_ls_number_reflns         3603
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.048
_refine_ls_R_factor_all          0.0948
_refine_ls_R_factor_gt           0.0676
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0695P)²+0.9647P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1622
_refine_ls_wR_factor_ref         0.1808
_reflns_number_gt                2627
_reflns_number_total             3603
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo051922tsi20050914_124615.cif
_cod_database_code               4021387
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
O1 O 1.0345(3) 0.92499(16) 1.07848(12) 0.0313(5) Uani 1 1 d .
O2 O 0.9544(3) 0.76992(17) 0.91781(12) 0.0314(5) Uani 1 1 d .
O3 O 0.3668(3) 0.89092(17) 0.90138(12) 0.0326(5) Uani 1 1 d .
H3 H 0.2288 0.9335 0.9015 0.039 Uiso 1 1 d R
C1 C 0.7948(4) 0.8709(2) 1.20524(17) 0.0283(6) Uani 1 1 d .
C2 C 0.9164(4) 0.8430(2) 1.12160(17) 0.0278(6) Uani 1 1 d .
C3 C 0.9151(4) 0.7367(2) 1.07861(17) 0.0278(6) Uani 1 1 d .
C4 C 0.7882(4) 0.6585(2) 1.12251(17) 0.0293(6) Uani 1 1 d .
H4 H 0.7868 0.5873 1.0947 0.035 Uiso 1 1 calc R
C5 C 0.6632(4) 0.6824(2) 1.20637(17) 0.0276(6) Uani 1 1 d .
C6 C 0.6705(4) 0.7903(2) 1.24588(17) 0.0280(6) Uani 1 1 d .
H6 H 0.5886 0.8087 1.3017 0.034 Uiso 1 1 calc R
C7 C 0.5261(5) 0.5958(2) 1.25581(18) 0.0321(6) Uani 1 1 d .
C8 C 0.2775(5) 0.6541(3) 1.2766(2) 0.0481(8) Uani 1 1 d .
H8A H 0.1944 0.6004 1.3093 0.072 Uiso 1 1 calc R
H8B H 0.2173 0.6739 1.2226 0.072 Uiso 1 1 calc R
H8C H 0.2639 0.7248 1.3111 0.072 Uiso 1 1 calc R
C9 C 0.5457(7) 0.4815(3) 1.2037(2) 0.0562(10) Uani 1 1 d .
H9A H 0.7027 0.4449 1.1898 0.084 Uiso 1 1 calc R
H9B H 0.4821 0.4991 1.1501 0.084 Uiso 1 1 calc R
H9C H 0.4647 0.4286 1.2384 0.084 Uiso 1 1 calc R
C10 C 0.6206(6) 0.5623(3) 1.3427(2) 0.0496(9) Uani 1 1 d .
H10A H 0.7800 0.5302 1.3300 0.074 Uiso 1 1 calc R
H10B H 0.5433 0.5042 1.3725 0.074 Uiso 1 1 calc R
H10C H 0.5973 0.6315 1.3796 0.074 Uiso 1 1 calc R
C11 C 1.0526(5) 0.7072(3) 0.98907(17) 0.0316(6) Uani 1 1 d .
H11A H 1.2026 0.7249 0.9895 0.038 Uiso 1 1 calc R
H11B H 1.0706 0.6228 0.9781 0.038 Uiso 1 1 calc R
C12 C 0.7696(5) 0.7221(3) 0.89415(18) 0.0330(6) Uani 1 1 d .
H12A H 0.6449 0.7330 0.9425 0.040 Uiso 1 1 calc R
H12B H 0.8173 0.6380 0.8815 0.040 Uiso 1 1 calc R
C13 C 0.6944(5) 0.7854(2) 0.81390(17) 0.0288(6) Uani 1 1 d .
C14 C 0.4909(5) 0.8680(2) 0.81949(17) 0.0288(6) Uani 1 1 d .
C15 C 0.4247(4) 0.9249(2) 0.74363(17) 0.0285(6) Uani 1 1 d .
C16 C 0.5618(4) 0.8974(2) 0.66318(18) 0.0288(6) Uani 1 1 d .
H16 H 0.5178 0.9362 0.6131 0.035 Uiso 1 1 calc R
C17 C 0.7635(4) 0.8137(2) 0.65448(17) 0.0276(6) Uani 1 1 d .
C18 C 0.8250(4) 0.7598(2) 0.73192(18) 0.0295(6) Uani 1 1 d .
H18 H 0.9593 0.7044 0.7284 0.035 Uiso 1 1 calc R
C19 C 0.9031(4) 0.7754(2) 0.56458(17) 0.0288(6) Uani 1 1 d .
C20 C 1.1540(5) 0.7818(3) 0.5648(2) 0.0396(7) Uani 1 1 d .
H20A H 1.1673 0.8622 0.5749 0.059 Uiso 1 1 calc R
H20B H 1.2397 0.7544 0.5088 0.059 Uiso 1 1 calc R
H20C H 1.2116 0.7328 0.6107 0.059 Uiso 1 1 calc R
C21 C 0.8851(5) 0.6467(3) 0.54512(19) 0.0371(7) Uani 1 1 d .
H21A H 0.9762 0.6208 0.4898 0.056 Uiso 1 1 calc R
H21B H 0.7297 0.6425 0.5422 0.056 Uiso 1 1 calc R
H21C H 0.9384 0.5965 0.5913 0.056 Uiso 1 1 calc R
C22 C 0.8187(5) 0.8519(3) 0.48895(18) 0.0370(7) Uani 1 1 d .
H22A H 0.8208 0.9334 0.5008 0.056 Uiso 1 1 calc R
H22B H 0.6665 0.8432 0.4840 0.056 Uiso 1 1 calc R
H22C H 0.9159 0.8269 0.4347 0.056 Uiso 1 1 calc R
C23 C 0.2029(5) 1.0133(2) 0.74805(18) 0.0306(6) Uani 1 1 d .
H23A H 0.0812 0.9776 0.7786 0.037 Uiso 1 1 calc R
H23B H 0.1708 1.0304 0.6885 0.037 Uiso 1 1 calc R
C24 C 1.2613(5) 0.9183(3) 1.1012(2) 0.0389(7) Uani 1 1 d .
H24A H 1.2519 0.9285 1.1638 0.058 Uiso 1 1 calc R
H24B H 1.3294 0.9796 1.0714 0.058 Uiso 1 1 calc R
H24C H 1.3522 0.8425 1.0833 0.058 Uiso 1 1 calc R
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_3
C2 O1 C24 114.1(2) .
C12 O2 C11 112.5(2) .
C6 C1 C2 118.4(2) .
C6 C1 C23 120.2(2) 2_677
C2 C1 C23 121.3(2) 2_677
C1 C2 O1 119.1(2) .
C1 C2 C3 121.5(2) .
O1 C2 C3 119.3(2) .
C4 C3 C2 117.8(2) .
C4 C3 C11 121.6(2) .
C2 C3 C11 120.5(2) .
C3 C4 C5 122.9(2) .
C4 C5 C6 116.7(2) .
C4 C5 C7 123.2(2) .
C6 C5 C7 120.1(2) .
C1 C6 C5 122.7(2) .
C8 C7 C9 109.2(3) .
C8 C7 C5 110.1(2) .
C9 C7 C5 112.4(2) .
C8 C7 C10 109.2(3) .
C9 C7 C10 107.4(3) .
C5 C7 C10 108.5(2) .
O2 C11 C3 114.1(2) .
O2 C12 C13 108.4(2) .
C18 C13 C14 118.8(2) .
C18 C13 C12 119.8(3) .
C14 C13 C12 121.4(2) .
O3 C14 C15 122.8(2) .
O3 C14 C13 117.1(2) .
C15 C14 C13 120.1(2) .
C16 C15 C14 119.1(2) .
C16 C15 C23 120.0(2) .
C14 C15 C23 120.9(2) .
C15 C16 C17 122.6(2) .
C18 C17 C16 116.5(2) .
C18 C17 C19 120.9(2) .
C16 C17 C19 122.4(2) .
C13 C18 C17 122.9(3) .
C17 C19 C22 112.7(2) .
C17 C19 C20 110.7(2) .
C22 C19 C20 108.0(2) .
C17 C19 C21 108.8(2) .
C22 C19 C21 107.7(2) .
C20 C19 C21 108.9(2) .
C15 C23 C1 113.5(2) 2_677
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C2 1.392(3) .
O1 C24 1.455(3) .
O2 C12 1.430(3) .
O2 C11 1.440(3) .
O3 C14 1.368(3) .
C1 C6 1.388(4) .
C1 C2 1.392(4) .
C1 C23 1.524(4) 2_677
C2 C3 1.399(4) .
C3 C4 1.396(4) .
C3 C11 1.506(4) .
C4 C5 1.397(4) .
C5 C6 1.399(4) .
C5 C7 1.537(4) .
C7 C8 1.519(4) .
C7 C9 1.524(4) .
C7 C10 1.540(4) .
C12 C13 1.504(4) .
C13 C18 1.388(4) .
C13 C14 1.401(4) .
C14 C15 1.398(4) .
C15 C16 1.388(4) .
C15 C23 1.519(4) .
C16 C17 1.397(4) .
C17 C18 1.397(4) .
C17 C19 1.532(4) .
C19 C22 1.534(4) .
C19 C20 1.537(4) .
C19 C21 1.540(4) .
C23 C1 1.524(4) 2_677
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O3 H3 O1 0.89 2.05 2.891(3) 159.2 2_677
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 11498639
