#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/61/2206118.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_2206118
loop_
_publ_author_name
'Abdelhak, Ettahiri'
'Merle, Daphne'
'Perrin, Monique'
'Thozet, Alain'
_publ_section_title
;
 p-Cumylcalix[4]arene--para-xylene (1/1)
;
_journal_issue                   7
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2001
_journal_page_last               o2002
_journal_paper_doi               10.1107/S1600536805016442
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C64 H64 O4, C8 H10'
_chemical_formula_moiety         'C64 H64 O4, C8 H10'
_chemical_formula_sum            'C72 H74 O4'
_chemical_formula_weight         1003.31
_chemical_name_common            'p-cumylcalix[4]arene--para-xylene (1/1)'
_chemical_name_systematic
;
4-(2-Phenylisopropyl)calix[4]arene--1,4-dimethylbenzene (1/1)
;
_space_group_IT_number           13
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yac'
_symmetry_space_group_name_H-M   'P 1 2/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                90.00
_cell_angle_beta                 96.62(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   14.66(3)
_cell_length_b                   12.62(3)
_cell_length_c                   15.14(3)
_cell_measurement_temperature    293(2)
_cell_volume                     2782(10)
_computing_cell_refinement       'Scalepack (Otwinowski & Minor, 1997)'
_computing_data_collection       'Collect (Nonius, 2000)'
_computing_data_reduction
'Denzo (Otwinowski & Minor, 1997) and Scalepack'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 9
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'φ or ω'
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0380
_diffrn_reflns_av_sigmaI/netI    0.0539
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            12312
_diffrn_reflns_theta_full        27.49
_diffrn_reflns_theta_max         27.49
_diffrn_reflns_theta_min         3.15
_exptl_absorpt_coefficient_mu    0.072
_exptl_absorpt_correction_T_max  0.9857
_exptl_absorpt_correction_T_min  0.9445
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.198
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1076
_exptl_crystal_size_max          0.80
_exptl_crystal_size_mid          0.50
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.453
_refine_diff_density_min         -0.188
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     351
_refine_ls_number_reflns         6372
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.016
_refine_ls_R_factor_all          0.0993
_refine_ls_R_factor_gt           0.0549
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0771P)²+0.6028P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1333
_refine_ls_wR_factor_ref         0.1547
_reflns_number_gt                4031
_reflns_number_total             6372
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bd6001.cif
_cod_data_source_block           I
_cod_original_sg_symbol_H-M      'P 2/n'
_cod_database_code               2206118
_cod_database_fobs_code          2206118
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z-1/2'
loop_
_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
_atom_site_type_symbol
O13 0.20582(9) 0.05806(9) 0.12855(8) 0.0319(3) Uani d . 1 O
O14 0.37116(9) 0.05843(10) 0.22388(8) 0.0322(3) Uani d . 1 O
C1 0.46942(12) -0.04090(15) 0.38132(11) 0.0298(4) Uani d . 1 C
H1A 0.5280 -0.0590 0.4143 0.036 Uiso calc R 1 H
H1B 0.4657 0.0358 0.3779 0.036 Uiso calc R 1 H
C12 0.10702(12) -0.08123(14) 0.06803(11) 0.0279(4) Uani d . 1 C
C2 0.46639(12) -0.08547(14) 0.28743(11) 0.0273(4) Uani d . 1 C
C14 0.41867(12) -0.03496(13) 0.21413(11) 0.0265(4) Uani d . 1 C
C4 0.51245(12) -0.22371(14) 0.18862(11) 0.0279(4) Uani d . 1 C
C13 0.19330(12) -0.03252(13) 0.07701(11) 0.0271(4) Uani d . 1 C
C8 0.26570(12) -0.07218(14) 0.03461(11) 0.0272(4) Uani d . 1 C
C6 0.41743(12) -0.07599(14) 0.12830(11) 0.0273(4) Uani d . 1 C
C7 0.36111(12) -0.02468(15) 0.04960(11) 0.0289(4) Uani d . 1 C
H7A 0.3917 -0.0345 -0.0033 0.035 Uiso calc R 1 H
H7B 0.3565 0.0508 0.0602 0.035 Uiso calc R 1 H
C11 0.09466(13) -0.16916(15) 0.01280(11) 0.0301(4) Uani d . 1 C
H11 0.0372 -0.2012 0.0050 0.036 Uiso calc R 1 H
C5 0.46495(12) -0.16913(14) 0.11760(11) 0.0290(4) Uani d . 1 C
H5 0.4652 -0.1964 0.0606 0.035 Uiso calc R 1 H
C40 0.56323(13) -0.32533(15) 0.16955(12) 0.0327(4) Uani d . 1 C
C10 0.16468(13) -0.21173(14) -0.03157(11) 0.0308(4) Uani d . 1 C
C9 0.24929(13) -0.16218(15) -0.01818(11) 0.0303(4) Uani d . 1 C
H9 0.2975 -0.1902 -0.0457 0.036 Uiso calc R 1 H
C3 0.51190(12) -0.17956(15) 0.27293(11) 0.0285(4) Uani d . 1 C
H3 0.5432 -0.2144 0.3214 0.034 Uiso calc R 1 H
C100 0.14674(14) -0.30593(15) -0.09561(12) 0.0349(4) Uani d . 1 C
C103 0.10026(13) -0.26560(16) -0.18622(12) 0.0334(4) Uani d . 1 C
C42 0.60837(15) -0.37815(16) 0.25528(13) 0.0394(5) Uani d . 1 C
H42A 0.6526 -0.3306 0.2856 0.059 Uiso calc R 1 H
H42B 0.6385 -0.4422 0.2405 0.059 Uiso calc R 1 H
H42C 0.5622 -0.3945 0.2932 0.059 Uiso calc R 1 H
C43 0.64065(13) -0.29801(16) 0.11258(12) 0.0358(5) Uani d . 1 C
C104 0.12549(14) -0.16827(17) -0.21980(12) 0.0392(5) Uani d . 1 C
H104 0.1679 -0.1258 -0.1857 0.047 Uiso calc R 1 H
C41 0.49366(15) -0.40372(17) 0.12225(14) 0.0440(5) Uani d . 1 C
H41A 0.4433 -0.4129 0.1569 0.066 Uiso calc R 1 H
H41B 0.5231 -0.4708 0.1157 0.066 Uiso calc R 1 H
H41C 0.4711 -0.3765 0.0646 0.066 Uiso calc R 1 H
C47 0.76271(16) -0.1811(2) 0.07941(17) 0.0596(7) Uani d . 1 C
H47 0.7949 -0.1180 0.0899 0.071 Uiso calc R 1 H
C106 0.02546(15) -0.1950(2) -0.35440(13) 0.0480(6) Uani d . 1 C
H106 0.0002 -0.1715 -0.4101 0.058 Uiso calc R 1 H
C102 0.23694(16) -0.35996(17) -0.11306(14) 0.0467(5) Uani d . 1 C
H10A 0.2704 -0.3807 -0.0575 0.070 Uiso calc R 1 H
H10B 0.2733 -0.3114 -0.1431 0.070 Uiso calc R 1 H
H10C 0.2235 -0.4215 -0.1495 0.070 Uiso calc R 1 H
C105 0.08829(15) -0.13408(19) -0.30310(13) 0.0454(5) Uani d . 1 C
H105 0.1061 -0.0691 -0.3245 0.055 Uiso calc R 1 H
C107 0.00033(16) -0.2909(2) -0.32280(14) 0.0509(6) Uani d . 1 C
H107 -0.0421 -0.3328 -0.3574 0.061 Uiso calc R 1 H
C48 0.69013(14) -0.20482(18) 0.12696(14) 0.0443(5) Uani d . 1 C
H48 0.6742 -0.1572 0.1695 0.053 Uiso calc R 1 H
C101 0.08758(19) -0.38921(18) -0.05491(14) 0.0531(6) Uani d . 1 C
H10D 0.0274 -0.3608 -0.0512 0.080 Uiso calc R 1 H
H10E 0.1156 -0.4075 0.0036 0.080 Uiso calc R 1 H
H10F 0.0828 -0.4514 -0.0917 0.080 Uiso calc R 1 H
C108 0.03761(14) -0.32626(18) -0.23939(13) 0.0424(5) Uani d . 1 C
H108 0.0201 -0.3919 -0.2191 0.051 Uiso calc R 1 H
C44 0.66673(17) -0.3675(2) 0.04907(14) 0.0520(6) Uani d . 1 C
H44 0.6350 -0.4308 0.0379 0.062 Uiso calc R 1 H
C46 0.78700(19) -0.2512(3) 0.01654(18) 0.0702(9) Uani d . 1 C
H46 0.8355 -0.2356 -0.0158 0.084 Uiso calc R 1 H
C45 0.7399(2) -0.3432(3) 0.00206(17) 0.0716(9) Uani d . 1 C
H45 0.7569 -0.3907 -0.0400 0.086 Uiso calc R 1 H
C504 0.2500 0.6358(2) 0.2500 0.0326(6) Uani d S 1 C
C503 0.18099(14) 0.58012(17) 0.20100(13) 0.0404(5) Uani d . 1 C
H503 0.1338 0.6166 0.1677 0.048 Uiso calc R 1 H
C501 0.2500 0.4130(2) 0.2500 0.0485(8) Uani d S 1 C
C502 0.18112(17) 0.46990(19) 0.20075(15) 0.0499(6) Uani d . 1 C
H502 0.1341 0.4337 0.1669 0.060 Uiso calc R 1 H
C506 0.2500 0.7552(2) 0.2500 0.0493(8) Uani d S 1 C
H50A 0.2144 0.7806 0.1970 0.074 Uiso calc PR 0.50 H
H50B 0.3119 0.7806 0.2518 0.074 Uiso calc PR 0.50 H
H50C 0.2236 0.7806 0.3012 0.074 Uiso calc PR 0.50 H
C505 0.2500 0.2936(3) 0.2500 0.0852(15) Uani d S 1 C
H50D 0.2642 0.2682 0.1934 0.128 Uiso calc PR 0.50 H
H50E 0.1905 0.2682 0.2606 0.128 Uiso calc PR 0.50 H
H50F 0.2953 0.2682 0.2960 0.128 Uiso calc PR 0.50 H
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
C12 C1 C2 2 . 113.81(17)
C12 C1 H1A 2 . 108.8
C2 C1 H1A . . 108.8
C12 C1 H1B 2 . 108.8
C2 C1 H1B . . 108.8
H1A C1 H1B . . 107.7
C11 C12 C13 . . 117.61(17)
C11 C12 C1 . 2 121.31(18)
C13 C12 C1 . 2 121.1(2)
C3 C2 C14 . . 118.01(18)
C3 C2 C1 . . 119.93(16)
C14 C2 C1 . . 122.1(2)
O14 C14 C2 . . 121.05(17)
O14 C14 C6 . . 117.50(16)
C2 C14 C6 . . 121.5(2)
C3 C4 C5 . . 117.0(2)
C3 C4 C40 . . 124.28(17)
C5 C4 C40 . . 118.70(18)
O13 C13 C8 . . 119.82(17)
O13 C13 C12 . . 118.51(16)
C8 C13 C12 . . 121.7(2)
C9 C8 C13 . . 117.79(18)
C9 C8 C7 . . 120.26(16)
C13 C8 C7 . . 121.8(2)
C5 C6 C14 . . 118.07(17)
C5 C6 C7 . . 120.44(18)
C14 C6 C7 . . 121.4(2)
C6 C7 C8 . . 111.03(17)
C6 C7 H7A . . 109.4
C8 C7 H7A . . 109.4
C6 C7 H7B . . 109.4
C8 C7 H7B . . 109.4
H7A C7 H7B . . 108.0
C12 C11 C10 . . 123.00(19)
C12 C11 H11 . . 118.5
C10 C11 H11 . . 118.5
C6 C5 C4 . . 122.83(18)
C6 C5 H5 . . 118.6
C4 C5 H5 . . 118.6
C4 C40 C41 . . 108.5(2)
C4 C40 C42 . . 112.08(18)
C41 C40 C42 . . 108.2(2)
C4 C40 C43 . . 108.93(18)
C41 C40 C43 . . 112.0(2)
C42 C40 C43 . . 107.2(2)
C9 C10 C11 . . 116.9(2)
C9 C10 C100 . . 121.83(17)
C11 C10 C100 . . 121.25(19)
C10 C9 C8 . . 123.03(18)
C10 C9 H9 . . 118.5
C8 C9 H9 . . 118.5
C2 C3 C4 . . 122.62(17)
C2 C3 H3 . . 118.7
C4 C3 H3 . . 118.7
C101 C100 C10 . . 109.8(2)
C101 C100 C102 . . 107.6(2)
C10 C100 C102 . . 111.30(18)
C101 C100 C103 . . 111.7(2)
C10 C100 C103 . . 109.3(2)
C102 C100 C103 . . 107.06(18)
C108 C103 C104 . . 117.5(2)
C108 C103 C100 . . 122.0(2)
C104 C103 C100 . . 120.32(18)
C40 C42 H42A . . 109.5
C40 C42 H42B . . 109.5
H42A C42 H42B . . 109.5
C40 C42 H42C . . 109.5
H42A C42 H42C . . 109.5
H42B C42 H42C . . 109.5
C48 C43 C44 . . 117.7(2)
C48 C43 C40 . . 120.50(18)
C44 C43 C40 . . 121.7(2)
C105 C104 C103 . . 120.9(2)
C105 C104 H104 . . 119.6
C103 C104 H104 . . 119.6
C40 C41 H41A . . 109.5
C40 C41 H41B . . 109.5
H41A C41 H41B . . 109.5
C40 C41 H41C . . 109.5
H41A C41 H41C . . 109.5
H41B C41 H41C . . 109.5
C46 C47 C48 . . 119.7(3)
C46 C47 H47 . . 120.1
C48 C47 H47 . . 120.1
C107 C106 C105 . . 119.3(2)
C107 C106 H106 . . 120.4
C105 C106 H106 . . 120.4
C100 C102 H10A . . 109.5
C100 C102 H10B . . 109.5
H10A C102 H10B . . 109.5
C100 C102 H10C . . 109.5
H10A C102 H10C . . 109.5
H10B C102 H10C . . 109.5
C106 C105 C104 . . 120.6(2)
C106 C105 H105 . . 119.7
C104 C105 H105 . . 119.7
C106 C107 C108 . . 120.6(2)
C106 C107 H107 . . 119.7
C108 C107 H107 . . 119.7
C47 C48 C43 . . 121.4(2)
C47 C48 H48 . . 119.3
C43 C48 H48 . . 119.3
C100 C101 H10D . . 109.5
C100 C101 H10E . . 109.5
H10D C101 H10E . . 109.5
C100 C101 H10F . . 109.5
H10D C101 H10F . . 109.5
H10E C101 H10F . . 109.5
C103 C108 C107 . . 121.1(2)
C103 C108 H108 . . 119.5
C107 C108 H108 . . 119.5
C43 C44 C45 . . 120.4(3)
C43 C44 H44 . . 119.8
C45 C44 H44 . . 119.8
C45 C46 C47 . . 119.7(3)
C45 C46 H46 . . 120.2
C47 C46 H46 . . 120.2
C46 C45 C44 . . 121.0(3)
C46 C45 H45 . . 119.5
C44 C45 H45 . . 119.5
C503 C504 C503 2 . 118.6(3)
C503 C504 C506 2 . 120.70(15)
C503 C504 C506 . . 120.70(15)
C504 C503 C502 . . 120.7(2)
C504 C503 H503 . . 119.6
C502 C503 H503 . . 119.6
C502 C501 C502 2 . 117.6(3)
C502 C501 C505 2 . 121.22(16)
C502 C501 C505 . . 121.22(16)
C501 C502 C503 . . 121.2(2)
C501 C502 H502 . . 119.4
C503 C502 H502 . . 119.4
C504 C506 H50A . . 109.5
C504 C506 H50B . . 109.5
H50A C506 H50B . . 109.5
C504 C506 H50C . . 109.5
H50A C506 H50C . . 109.5
H50B C506 H50C . . 109.5
C501 C505 H50D . . 109.5
C501 C505 H50E . . 109.5
H50D C505 H50E . . 109.5
C501 C505 H50F . . 109.5
H50D C505 H50F . . 109.5
H50E C505 H50F . . 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
O13 C13 . 1.384(3)
O14 C14 . 1.386(3)
C1 C12 2 1.517(3)
C1 C2 . 1.525(4)
C1 H1A . 0.9700
C1 H1B . 0.9700
C12 C11 . 1.389(3)
C12 C13 . 1.399(3)
C12 C1 2 1.517(3)
C2 C3 . 1.392(4)
C2 C14 . 1.396(3)
C14 C6 . 1.397(3)
C4 C3 . 1.394(3)
C4 C5 . 1.394(3)
C4 C40 . 1.527(4)
C13 C8 . 1.395(3)
C8 C9 . 1.394(3)
C8 C7 . 1.515(4)
C6 C5 . 1.385(4)
C6 C7 . 1.514(3)
C7 H7A . 0.9700
C7 H7B . 0.9700
C11 C10 . 1.397(3)
C11 H11 . 0.9300
C5 H5 . 0.9300
C40 C41 . 1.537(3)
C40 C42 . 1.539(3)
C40 C43 . 1.542(3)
C10 C9 . 1.383(4)
C10 C100 . 1.537(4)
C9 H9 . 0.9300
C3 H3 . 0.9300
C100 C101 . 1.536(4)
C100 C102 . 1.537(4)
C100 C103 . 1.546(3)
C103 C108 . 1.381(3)
C103 C104 . 1.395(4)
C42 H42A . 0.9600
C42 H42B . 0.9600
C42 H42C . 0.9600
C43 C48 . 1.386(4)
C43 C44 . 1.387(3)
C104 C105 . 1.384(4)
C104 H104 . 0.9300
C41 H41A . 0.9600
C41 H41B . 0.9600
C41 H41C . 0.9600
C47 C46 . 1.377(5)
C47 C48 . 1.385(4)
C47 H47 . 0.9300
C106 C107 . 1.366(4)
C106 C105 . 1.371(4)
C106 H106 . 0.9300
C102 H10A . 0.9600
C102 H10B . 0.9600
C102 H10C . 0.9600
C105 H105 . 0.9300
C107 C108 . 1.391(4)
C107 H107 . 0.9300
C48 H48 . 0.9300
C101 H10D . 0.9600
C101 H10E . 0.9600
C101 H10F . 0.9600
C108 H108 . 0.9300
C44 C45 . 1.389(4)
C44 H44 . 0.9300
C46 C45 . 1.354(5)
C46 H46 . 0.9300
C45 H45 . 0.9300
C504 C503 2 1.376(3)
C504 C503 . 1.376(3)
C504 C506 . 1.507(5)
C503 C502 . 1.391(5)
C503 H503 . 0.9300
C501 C502 2 1.384(3)
C501 C502 . 1.384(3)
C501 C505 . 1.507(6)
C502 H502 . 0.9300
C506 H50A . 0.9600
C506 H50B . 0.9600
C506 H50C . 0.9600
C505 H50D . 0.9600
C505 H50E . 0.9600
C505 H50F . 0.9600
