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#$Date: 2016-03-21 02:27:53 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178391 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/13/4021390.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_4021390
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            'C49 H66 O6'
_chemical_formula_weight         751.02
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 106.728(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   13.5929(12)
_cell_length_b                   9.3211(7)
_cell_length_c                   17.7157(11)
_cell_measurement_reflns_used    15405
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.68
_cell_measurement_theta_min      4.12
_cell_volume                     2149.6(3)
_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 0.959
_diffrn_measured_fraction_theta_max 0.959
_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  0.0462
_diffrn_reflns_av_sigmaI/netI    0.0751
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            15405
_diffrn_reflns_theta_full        25.68
_diffrn_reflns_theta_max         25.68
_diffrn_reflns_theta_min         4.12
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  0
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.160
_exptl_crystal_density_meas      ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             816
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_refine_diff_density_max         0.904
_refine_diff_density_min         -0.392
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.991
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     261
_refine_ls_number_reflns         3919
_refine_ls_number_restraints     24
_refine_ls_restrained_S_all      1.036
_refine_ls_R_factor_all          0.1285
_refine_ls_R_factor_gt           0.0928
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0853P)²+4.8386P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2114
_refine_ls_wR_factor_ref         0.2354
_reflns_number_gt                2742
_reflns_number_total             3919
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo051922tsi20050915_042446.cif
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               4021390
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'
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 0.5663(2) 0.7775(3) 1.19060(17) 0.0433(8) Uani 1 1 d .
O2 O 0.4789(2) 0.7573(3) 0.9531(3) 0.0633(11) Uani 1 1 d U
O3 O 0.4699(2) 0.5916(3) 0.7941(2) 0.0507(9) Uani 1 1 d .
C1 C 0.6676(3) 0.5636(4) 1.1976(2) 0.0284(8) Uani 1 1 d .
C2 C 0.6354(3) 0.6976(4) 1.1642(2) 0.0318(9) Uani 1 1 d .
C3 C 0.6752(3) 0.7534(4) 1.1060(2) 0.0372(10) Uani 1 1 d .
C4 C 0.7473(3) 0.6721(4) 1.0820(2) 0.0347(9) Uani 1 1 d .
H4 H 0.7742 0.7093 1.0435 0.042 Uiso 1 1 calc R
C5 C 0.7804(3) 0.5378(4) 1.1135(2) 0.0290(8) Uani 1 1 d .
C6 C 0.7409(3) 0.4875(4) 1.1726(2) 0.0283(8) Uani 1 1 d .
H6 H 0.7642 0.4001 1.1964 0.034 Uiso 1 1 calc R
C7 C 0.8567(3) 0.4493(4) 1.0839(2) 0.0310(8) Uani 1 1 d .
C8 C 0.9651(3) 0.4735(5) 1.1395(3) 0.0491(12) Uani 1 1 d .
H8A H 1.0136 0.4175 1.1219 0.074 Uiso 1 1 calc R
H8B H 0.9670 0.4449 1.1919 0.074 Uiso 1 1 calc R
H8C H 0.9826 0.5733 1.1394 0.074 Uiso 1 1 calc R
C9 C 0.8312(4) 0.2888(4) 1.0855(3) 0.0419(10) Uani 1 1 d .
H9A H 0.7648 0.2705 1.0493 0.063 Uiso 1 1 calc R
H9B H 0.8308 0.2622 1.1378 0.063 Uiso 1 1 calc R
H9C H 0.8821 0.2334 1.0705 0.063 Uiso 1 1 calc R
C10 C 0.8544(4) 0.4894(5) 1.0006(2) 0.0437(11) Uani 1 1 d .
H10A H 0.7852 0.4827 0.9668 0.066 Uiso 1 1 calc R
H10B H 0.8976 0.4249 0.9822 0.066 Uiso 1 1 calc R
H10C H 0.8789 0.5858 0.9999 0.066 Uiso 1 1 calc R
C11 C 0.6393(4) 0.8968(5) 1.0658(3) 0.0459(11) Uani 1 1 d .
H11A H 0.5720 0.9198 1.0711 0.055 Uiso 1 1 calc R
H11B H 0.6865 0.9718 1.0916 0.055 Uiso 1 1 calc R
C12 C 0.6339(3) 0.8915(4) 0.9796(2) 0.0288(8) Uani 1 1 d .
C13 C 0.5541(3) 0.8165(4) 0.9258(3) 0.0380(10) Uani 1 1 d .
C14 C 0.5524(4) 0.8052(4) 0.8473(3) 0.0449(11) Uani 1 1 d .
C15 C 0.6318(4) 0.8633(4) 0.8230(2) 0.0455(11) Uani 1 1 d .
H15 H 0.6306 0.8536 0.7705 0.055 Uiso 1 1 calc R
C16 C 0.7127(3) 0.9352(4) 0.8738(2) 0.0344(9) Uani 1 1 d .
C17 C 0.7110(3) 0.9506(4) 0.9519(2) 0.0274(8) Uani 1 1 d .
H17 H 0.7634 1.0023 0.9866 0.033 Uiso 1 1 calc R
C18 C 0.8036(4) 0.9933(5) 0.8475(3) 0.0553(13) Uani 1 1 d .
C19 C 0.8864(7) 0.8876(11) 0.8695(7) 0.086(3) Uani 1 1 d U
H19A H 0.9304 0.8983 0.8360 0.128 Uiso 1 1 calc R
H19B H 0.8577 0.7928 0.8635 0.128 Uiso 1 1 calc R
H19C H 0.9257 0.9024 0.9234 0.128 Uiso 1 1 calc R
C20 C 0.7726(7) 1.0040(9) 0.7550(4) 0.108(3) Uani 1 1 d U
H20A H 0.7063 1.0482 0.7361 0.162 Uiso 1 1 calc R
H20B H 0.7702 0.9095 0.7329 0.162 Uiso 1 1 calc R
H20C H 0.8225 1.0608 0.7395 0.162 Uiso 1 1 calc R
C21 C 0.8298(4) 1.1450(6) 0.8754(3) 0.0582(14) Uani 1 1 d .
H21A H 0.7724 1.2065 0.8522 0.087 Uiso 1 1 calc R
H21B H 0.8885 1.1768 0.8601 0.087 Uiso 1 1 calc R
H21C H 0.8453 1.1484 0.9318 0.087 Uiso 1 1 calc R
C22 C 0.4639(5) 0.7325(5) 0.7887(4) 0.082(2) Uani 1 1 d U
H22A H 0.4000 0.7638 0.7975 0.098 Uiso 1 1 calc R
H22B H 0.4629 0.7612 0.7359 0.098 Uiso 1 1 calc R
C23 C 0.3847(3) 0.5075(4) 0.7479(2) 0.0323(8) Uani 1 1 d .
H23A H 0.4091 0.4353 0.7182 0.039 Uiso 1 1 calc R
H23B H 0.3364 0.5689 0.7108 0.039 Uiso 1 1 calc R
C24 C 0.4593(4) 0.7476(5) 1.1499(3) 0.0544(13) Uani 1 1 d .
H24A H 0.4461 0.7679 1.0948 0.082 Uiso 1 1 calc R
H24B H 0.4161 0.8069 1.1713 0.082 Uiso 1 1 calc R
H24C H 0.4449 0.6485 1.1568 0.082 Uiso 1 1 calc R
C25 C 0.4894(6) 0.6055(8) 0.9785(4) 0.0541(17) Uani 0.50 1 d P
H25A H 0.4914 0.5457 0.9348 0.081 Uiso 0.50 1 calc PR
H25B H 0.4318 0.5787 0.9966 0.081 Uiso 0.50 1 calc PR
H25C H 0.5517 0.5935 1.0205 0.081 Uiso 0.50 1 calc PR
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 114.2(3) .
C13 O2 C25 118.5(4) .
C22 O3 C23 118.5(3) .
C6 C1 C2 119.0(3) .
C6 C1 C23 119.4(3) 3_667
C2 C1 C23 121.1(3) 3_667
O1 C2 C3 119.7(3) .
O1 C2 C1 119.9(3) .
C3 C2 C1 120.4(3) .
C2 C3 C4 118.5(3) .
C2 C3 C11 122.1(3) .
C4 C3 C11 119.4(3) .
C5 C4 C3 122.7(4) .
C6 C5 C4 117.0(3) .
C6 C5 C7 121.6(3) .
C4 C5 C7 121.4(3) .
C5 C6 C1 122.3(3) .
C10 C7 C5 112.0(3) .
C10 C7 C8 109.6(4) .
C5 C7 C8 108.7(3) .
C10 C7 C9 108.5(3) .
C5 C7 C9 109.8(3) .
C8 C7 C9 108.1(4) .
C12 C11 C3 111.1(3) .
C17 C12 C13 117.9(3) .
C17 C12 C11 121.5(4) .
C13 C12 C11 120.4(4) .
O2 C13 C14 121.7(4) .
O2 C13 C12 118.0(4) .
C14 C13 C12 120.3(4) .
C15 C14 C13 119.5(4) .
C15 C14 C22 120.1(5) .
C13 C14 C22 120.3(5) .
C16 C15 C14 122.3(4) .
C15 C16 C17 117.4(4) .
C15 C16 C18 122.1(4) .
C17 C16 C18 120.5(4) .
C12 C17 C16 122.5(4) .
C19 C18 C21 117.0(7) .
C19 C18 C16 107.8(5) .
C21 C18 C16 111.4(4) .
C19 C18 C20 106.0(7) .
C21 C18 C20 104.5(4) .
C16 C18 C20 109.9(5) .
O3 C22 C14 112.2(4) .
O3 C23 C1 108.9(3) 3_667
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C2 1.382(4) .
O1 C24 1.453(6) .
O2 C13 1.368(5) .
O2 C25 1.479(7) .
O2 O3 3.185(5) .
O3 C22 1.318(5) .
O3 C23 1.442(4) .
C1 C6 1.395(5) .
C1 C2 1.397(5) .
C1 C23 1.508(5) 3_667
C2 C3 1.395(5) .
C3 C4 1.398(5) .
C3 C11 1.527(5) .
C4 C5 1.391(5) .
C5 C6 1.389(5) .
C5 C7 1.531(5) .
C7 C10 1.514(5) .
C7 C8 1.535(5) .
C7 C9 1.539(6) .
C11 C12 1.508(5) .
C12 C17 1.393(5) .
C12 C13 1.406(6) .
C13 C14 1.388(7) .
C14 C15 1.382(7) .
C14 C22 1.506(6) .
C15 C16 1.378(6) .
C16 C17 1.397(5) .
C16 C18 1.541(6) .
C18 C19 1.462(9) .
C18 C21 1.507(7) .
C18 C20 1.573(9) .
C23 C1 1.508(5) 3_667
