#------------------------------------------------------------------------------
#$Date: 2016-02-20 18:35:30 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176787 $
#$URL: svn://www.crystallography.net/cod/cif/2/21/12/2211258.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2211258
loop_
_publ_author_name
'Yang, Yong'
'Li, En-Chao'
'Chen, Feng-Xiang'
'Peng, Cheng'
'Shi, Xian-Fa'
_publ_section_title
;
 5,17-Dibenzoyl-25,26,27,28-tetrahydroxycalix[4]arene
;
_journal_coeditor_code           AT2150
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o5563
_journal_page_last               o5564
_journal_paper_doi               10.1107/S1600536806046691
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C42 H32 O6'
_chemical_formula_moiety         'C42 H32 O6'
_chemical_formula_sum            'C42 H32 O6'
_chemical_formula_weight         632.68
_chemical_name_systematic
;
5,17-Dibenzoyl-25,26,27,28-tetrahydroxycalix[4]arene
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL97
_cell_angle_alpha                90.00
_cell_angle_beta                 116.187(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   18.615(4)
_cell_length_b                   15.609(4)
_cell_length_c                   12.220(3)
_cell_measurement_reflns_used    896
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      19.391
_cell_measurement_theta_min      2.438
_cell_volume                     3186.2(13)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Bruker, 1997)'
_computing_data_reduction        'SHELXTL (Bruker, 1997)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_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  0.0803
_diffrn_reflns_av_sigmaI/netI    0.1099
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            6625
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         1.79
_diffrn_standards_decay_%        4.19
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  0.9913
_exptl_absorpt_correction_T_min  0.9827
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker,  1997)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       pillar
_exptl_crystal_F_000             1328
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.181
_refine_diff_density_min         -0.182
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.904
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     225
_refine_ls_number_reflns         2819
_refine_ls_number_restraints     2
_refine_ls_restrained_S_all      0.904
_refine_ls_R_factor_all          0.1481
_refine_ls_R_factor_gt           0.0646
_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)+(0.0737P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1418
_refine_ls_wR_factor_ref         0.1744
_reflns_number_gt                1253
_reflns_number_total             2819
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            at2150.cif
_cod_data_source_block           2
_cod_original_cell_volume        3186.1(13)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2211258
_cod_database_fobs_code          2211258
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
O O1 0.61452(15) 0.21936(16) 0.3326(3) 0.0742(8) Uani d D 1
O O2 0.49643(16) 0.22187(18) 0.3994(3) 0.0750(8) Uani d D 1
O O3 0.7746(2) 0.5782(2) 0.3615(3) 0.1147(11) Uani d . 1
C C1 0.6587(2) 0.2909(3) 0.1571(4) 0.0770(12) Uani d . 1
H H1A 0.7021 0.3013 0.1351 0.092 Uiso calc R 1
H H1B 0.6538 0.2295 0.1633 0.092 Uiso calc R 1
C C2 0.67922(19) 0.3318(2) 0.2804(3) 0.0615(10) Uani d . 1
C C3 0.72060(19) 0.4082(2) 0.3116(3) 0.0649(10) Uani d . 1
H H3A 0.7364 0.4334 0.2568 0.078 Uiso calc R 1
C C4 0.73931(19) 0.4484(2) 0.4211(4) 0.0614(10) Uani d . 1
C C5 0.7140(2) 0.4102(2) 0.5006(3) 0.0639(10) Uani d . 1
H H5A 0.7261 0.4367 0.5749 0.077 Uiso calc R 1
C C6 0.67166(19) 0.3344(2) 0.4737(3) 0.0586(9) Uani d . 1
C C7 0.6449(2) 0.2963(2) 0.5640(3) 0.0733(11) Uani d . 1
H H7A 0.6844 0.3100 0.6461 0.088 Uiso calc R 1
H H7B 0.6429 0.2344 0.5556 0.088 Uiso calc R 1
C C8 0.5631(2) 0.3286(3) 0.5467(3) 0.0648(10) Uani d . 1
C C9 0.5585(3) 0.3974(3) 0.6149(4) 0.0835(13) Uani d . 1
H H9A 0.6053 0.4221 0.6730 0.100 Uiso calc R 1
C C10 0.4856(3) 0.4296(3) 0.5976(4) 0.0954(14) Uani d . 1
H H10A 0.4832 0.4756 0.6441 0.114 Uiso calc R 1
C C11 0.4164(3) 0.3938(3) 0.5117(4) 0.0860(13) Uani d . 1
H H11A 0.3673 0.4162 0.5005 0.103 Uiso calc R 1
C C12 0.4179(2) 0.3255(3) 0.4417(3) 0.0664(10) Uani d . 1
C C13 0.4923(2) 0.2930(3) 0.4626(3) 0.0629(10) Uani d . 1
C C14 0.65515(19) 0.2961(2) 0.3638(4) 0.0599(10) Uani d . 1
C C15 0.7816(2) 0.5317(3) 0.4477(4) 0.0774(11) Uani d . 1
C C16 0.8328(2) 0.5604(3) 0.5748(4) 0.0767(11) Uani d . 1
C C17 0.8709(2) 0.5027(3) 0.6703(4) 0.0882(13) Uani d . 1
H H17A 0.8638 0.4441 0.6556 0.106 Uiso calc R 1
C C18 0.9189(3) 0.5319(4) 0.7862(5) 0.1055(16) Uani d . 1
H H18A 0.9440 0.4930 0.8496 0.127 Uiso calc R 1
C C19 0.9299(3) 0.6176(4) 0.8081(6) 0.1150(19) Uani d . 1
H H19A 0.9622 0.6372 0.8866 0.138 Uiso calc R 1
C C20 0.8929(3) 0.6761(4) 0.7136(6) 0.1131(18) Uani d . 1
H H20A 0.9003 0.7346 0.7287 0.136 Uiso calc R 1
C C21 0.8458(3) 0.6471(3) 0.5991(5) 0.0901(14) Uani d . 1
H H21A 0.8219 0.6863 0.5359 0.108 Uiso calc R 1
H H1 0.578(2) 0.214(4) 0.358(5) 0.16(3) Uiso d D 1
H H2 0.465(2) 0.217(3) 0.3275(19) 0.095(17) Uiso d D 1
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
C14 O1 H1 . . 114(4)
C13 O2 H2 . . 120(3)
C12 C1 C2 2_655 . 112.2(3)
C12 C1 H1A 2_655 . 109.2
C2 C1 H1A . . 109.2
C12 C1 H1B 2_655 . 109.2
C2 C1 H1B . . 109.2
H1A C1 H1B . . 107.9
C3 C2 C14 . . 117.6(4)
C3 C2 C1 . . 120.2(4)
C14 C2 C1 . . 122.2(3)
C4 C3 C2 . . 122.3(4)
C4 C3 H3A . . 118.8
C2 C3 H3A . . 118.8
C3 C4 C5 . . 117.8(3)
C3 C4 C15 . . 119.8(4)
C5 C4 C15 . . 122.4(4)
C6 C5 C4 . . 122.5(4)
C6 C5 H5A . . 118.8
C4 C5 H5A . . 118.8
C14 C6 C5 . . 117.6(4)
C14 C6 C7 . . 122.4(3)
C5 C6 C7 . . 120.0(4)
C6 C7 C8 . . 113.4(3)
C6 C7 H7A . . 108.9
C8 C7 H7A . . 108.9
C6 C7 H7B . . 108.9
C8 C7 H7B . . 108.9
H7A C7 H7B . . 107.7
C13 C8 C9 . . 117.9(4)
C13 C8 C7 . . 122.4(4)
C9 C8 C7 . . 119.7(4)
C10 C9 C8 . . 120.7(4)
C10 C9 H9A . . 119.7
C8 C9 H9A . . 119.7
C11 C10 C9 . . 120.0(5)
C11 C10 H10A . . 120.0
C9 C10 H10A . . 120.0
C10 C11 C12 . . 121.4(4)
C10 C11 H11A . . 119.3
C12 C11 H11A . . 119.3
C11 C12 C13 . . 117.5(4)
C11 C12 C1 . 2_655 120.3(4)
C13 C12 C1 . 2_655 122.1(4)
O2 C13 C8 . . 118.1(4)
O2 C13 C12 . . 119.4(4)
C8 C13 C12 . . 122.5(4)
C6 C14 O1 . . 120.4(4)
C6 C14 C2 . . 122.2(3)
O1 C14 C2 . . 117.3(4)
O3 C15 C4 . . 118.9(4)
O3 C15 C16 . . 119.3(4)
C4 C15 C16 . . 121.8(4)
C21 C16 C17 . . 118.4(4)
C21 C16 C15 . . 119.3(4)
C17 C16 C15 . . 122.2(4)
C18 C17 C16 . . 120.4(4)
C18 C17 H17A . . 119.8
C16 C17 H17A . . 119.8
C19 C18 C17 . . 120.0(5)
C19 C18 H18A . . 120.0
C17 C18 H18A . . 120.0
C18 C19 C20 . . 120.3(5)
C18 C19 H19A . . 119.8
C20 C19 H19A . . 119.8
C21 C20 C19 . . 119.5(5)
C21 C20 H20A . . 120.2
C19 C20 H20A . . 120.2
C20 C21 C16 . . 121.3(5)
C20 C21 H21A . . 119.4
C16 C21 H21A . . 119.4
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
O1 C14 . 1.378(4)
O1 H1 . 0.863(19)
O2 C13 . 1.373(4)
O2 H2 . 0.817(19)
O3 C15 . 1.238(4)
C1 C12 2_655 1.505(5)
C1 C2 . 1.522(5)
C1 H1A . 0.9700
C1 H1B . 0.9700
C2 C3 . 1.378(5)
C2 C14 . 1.397(5)
C3 C4 . 1.376(5)
C3 H3A . 0.9300
C4 C5 . 1.388(5)
C4 C15 . 1.479(5)
C5 C6 . 1.379(5)
C5 H5A . 0.9300
C6 C14 . 1.376(5)
C6 C7 . 1.517(5)
C7 C8 . 1.527(5)
C7 H7A . 0.9700
C7 H7B . 0.9700
C8 C13 . 1.381(5)
C8 C9 . 1.385(5)
C9 C10 . 1.373(6)
C9 H9A . 0.9300
C10 C11 . 1.372(6)
C10 H10A . 0.9300
C11 C12 . 1.374(5)
C11 H11A . 0.9300
C12 C13 . 1.388(5)
C12 C1 2_655 1.505(5)
C15 C16 . 1.488(5)
C16 C21 . 1.383(5)
C16 C17 . 1.396(5)
C17 C18 . 1.376(5)
C17 H17A . 0.9300
C18 C19 . 1.363(6)
C18 H18A . 0.9300
C19 C20 . 1.393(7)
C19 H19A . 0.9300
C20 C21 . 1.360(6)
C20 H20A . 0.9300
C21 H21A . 0.9300
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C17 H17A O1 7_656 0.93 2.58 3.478(5) 163.1
O2 H2 O1 2_655 0.817(19) 1.86(2) 2.672(4) 171(4)
O1 H1 O2 . 0.863(19) 1.81(2) 2.662(4) 169(6)
