#------------------------------------------------------------------------------
#$Date: 2016-08-07 11:16:30 +0300 (Sun, 07 Aug 2016) $
#$Revision: 185198 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/22/44/7224458.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_7224458
loop_
_publ_author_name
'Slavík, Petr'
'Eigner, Václav'
'Lhoták, Pavel'
_publ_section_title
;
 Shaping of calix[4]arenes via double bridging of the upper rim
;
_journal_issue                   26
_journal_name_full               CrystEngComm
_journal_page_first              4964
_journal_paper_doi               10.1039/C6CE00314A
_journal_volume                  18
_journal_year                    2016
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C42 H44 O6, 0.536(C H2 Cl2)'
_chemical_formula_sum            'C42.54 H45.07 Cl1.07 O6'
_chemical_formula_weight         690.30
_space_group_IT_number           113
_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_Hall  'P -4 2ab'
_symmetry_space_group_name_H-M   'P -4 21 m'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_update_record
;
2016-02-03 deposited with the CCDC.
2016-02-29 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   13.8543(10)
_cell_length_b                   13.8543(10)
_cell_length_c                   9.9079(10)
_cell_measurement_reflns_used    6000
_cell_measurement_temperature    180
_cell_measurement_theta_max      76
_cell_measurement_theta_min      5
_cell_volume                     1901.7(3)
_computing_cell_refinement       'CrysAlis, (Oxford Diffraction, 2002)'
_computing_data_collection       'Xcalibur, (Oxford Diffraction, 2002)'
_computing_data_reduction        'CrysAlis, (Oxford Diffraction, 2002)'
_computing_molecular_graphics    'CAMERON (Watkin et al., 1996)'
_computing_publication_material  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_refinement  'CRYSTALS (Betteridge et al., 2003)'
_computing_structure_solution    'Superflip (Palatinus & Chapuis, 2007)'
_diffrn_ambient_pressure         101
_diffrn_ambient_temperature      180
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device       Area
_diffrn_measurement_device_type  'Oxford Diffraction XCALIBUR'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.040
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            10619
_diffrn_reflns_theta_full        69.837
_diffrn_reflns_theta_max         75.910
_diffrn_reflns_theta_min         4.463
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    1.300
_exptl_absorpt_correction_T_max  0.69
_exptl_absorpt_correction_T_min  0.37
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'CrysAlis, (Oxford Diffraction, 2002)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.205
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             732.997
_exptl_crystal_size_max          0.650
_exptl_crystal_size_mid          0.410
_exptl_crystal_size_min          0.290
_refine_diff_density_max         0.20
_refine_diff_density_min         -0.20
_refine_ls_abs_structure_details 'Flack (1983), 871 Friedel-pairs'
_refine_ls_abs_structure_Flack   0.00(6)
_refine_ls_extinction_method     None
_refine_ls_goodness_of_fit_ref   0.9885
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     159
_refine_ls_number_reflns         2047
_refine_ls_number_restraints     55
_refine_ls_R_factor_all          0.0622
_refine_ls_R_factor_gt           0.0584
_refine_ls_shift/su_max          0.0078419
_refine_ls_shift/su_mean         0.0001567
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
;
 Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) 
 [weight] = 1.0/[A₀*T₀(x)+A₁*T₁(x) ... +Aₙ₋₁]*Tₙ₋₁(x)] 
 where Ai are the Chebychev coefficients listed below and x= Fcalc/Fmax 
 Method = Robust Weighting (Prince, 1982) 
 W = [weight] * [1-(deltaF/6*sigmaF)²]² 
 Ai are: 
 0.222E+04 0.373E+04 0.225E+04 908. 196. 
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1459
_refine_ls_wR_factor_gt          0.1417
_refine_ls_wR_factor_ref         0.1459
_reflns_limit_h_max              12
_reflns_limit_h_min              -12
_reflns_limit_k_max              17
_reflns_limit_k_min              0
_reflns_limit_l_max              11
_reflns_limit_l_min              0
_reflns_number_gt                1848
_reflns_number_total             2057
_reflns_threshold_expression     I>2.0σ(I)
_oxford_diffrn_Wilson_B_factor   0.00
_oxford_diffrn_Wilson_scale      0.00
_oxford_refine_ls_r_factor_ref   0.0622
_oxford_refine_ls_scale          6.0(2)
_oxford_reflns_number_all        2047
_oxford_reflns_threshold_expression_ref I>0.0\s(I)
_cod_data_source_file            c6ce00314a2.cif
_cod_data_source_block           8_PE456_2_4
_cod_depositor_comments
'Adding full bibliography for 7224456--7224459.cif.'
_cod_original_sg_symbol_Hall     'P -4 2ab '
_cod_original_sg_symbol_H-M      'P -4 21 m '
_cod_database_code               7224458
_iucr_refine_instruction_details_constraints
;
BLOCK SCALE X'S, U'S 
EQUIVALENCE PART(1001, OCC) PART(1002, OCC) 
EQUIVALENCE PART(2001, OCC) 
WEIGHT -1 PART(1002, OCC) 
CONT ENANTIO 
RIDE C   (   1,X'S) H   (  11,X'S) H   (  12,X'S) 
RIDE C   (   4,X'S) H   (  41,X'S) 
RIDE C   (   5,X'S) H   (  51,X'S) 
RIDE C   (   7,X'S) H   (  71,X'S) H   (  72,X'S) 
RIDE C   (  12,X'S) H   ( 121,X'S) H   ( 122,X'S) 
RIDE C   (  13,X'S) H   ( 131,X'S) H   ( 132,X'S) 
RIDE C   (  14,X'S) H   ( 141,X'S) H   ( 142,X'S) H   ( 143,X'S) 
RIDE C   ( 112,X'S) H   (1121,X'S) H   (1122,X'S) 
RIDE C   ( 113,X'S) H   (1131,X'S) H   (1132,X'S) 
RIDE C   ( 114,X'S) H   (1143,X'S) H   (1142,X'S) H   (1141,X'S) 
RIDE C   ( 901,X'S) H   (9011,X'S) 
END                                                                             
;
_iucr_refine_instruction_details_restraints
;
NO 
DISTANCE 1.460000 , 0.005000 = O(11) TO C(12) 
DISTANCE 1.510000 , 0.005000 = C(12) TO C(13) 
DISTANCE 1.540000 , 0.005000 = C(13) TO C(14) 
ANGLE 109.000000 , 1.000000 = O(11) TO C(12) TO C(13) 
ANGLE 109.000000 , 1.000000 = C(12) TO C(13) TO C(14) 
DISTANCE 1.460000 , 0.005000 = O(11) TO C(112) 
DISTANCE 1.510000 , 0.005000 = C(112) TO C(113) 
DISTANCE 1.540000 , 0.005000 = C(113) TO C(114) 
ANGLE 109.000000 , 1.000000 = O(11) TO C(112) TO C(113) 
ANGLE 109.000000 , 1.000000 = C(112) TO C(113) TO C(114) 
U(IJ)'S  0.0, 0.010000 = O(11) TO C(12) 
U(IJ)'S  0.0, 0.010000 = O(11) TO C(13) 
U(IJ)'S  0.0, 0.010000 = O(11) TO C(14) 
U(IJ)'S  0.0, 0.010000 = O(11) TO C(112) 
U(IJ)'S  0.0, 0.010000 = O(11) TO C(113) 
U(IJ)'S  0.0, 0.010000 = O(11) TO C(114) 
REM   HREST   START (DO NOT REMOVE THIS LINE) 
REM   HREST   END (DO NOT REMOVE THIS LINE) 
END                                                                             
;
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
y,-x,-z
-x,-y,z
-y,x,-z
-x+1/2,y+1/2,-z
-y+1/2,-x+1/2,z
x+1/2,-y+1/2,-z
y+1/2,x+1/2,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_occupancy
_atom_site_adp_type
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.1385(2) 0.6385(2) -0.1013(4) 0.0618 1.0000 Uani S T . . .
C2 C 0.18646(17) 0.56052(18) -0.1843(3) 0.0578 1.0000 Uani . . . . .
C3 C 0.20367(17) 0.57706(19) -0.3218(3) 0.0604 1.0000 Uani . . . . .
C4 C 0.2437(2) 0.5048(2) -0.4005(3) 0.0671 1.0000 Uani . . . . .
C5 C 0.25366(19) 0.4127(2) -0.3511(3) 0.0661 1.0000 Uani . . . . .
C6 C 0.23019(17) 0.39270(18) -0.2161(3) 0.0603 1.0000 Uani . . . . .
C7 C 0.21105(18) 0.28895(18) -0.1741(4) 0.0675 1.0000 Uani S T . . .
C8 C 0.20625(17) 0.46972(19) -0.1317(3) 0.0585 1.0000 Uani . . . . .
C9 C 0.16624(18) 0.66624(18) -0.3856(4) 0.0638 1.0000 Uani S T . . .
O10 O 0.19914(16) 0.69914(16) -0.4912(4) 0.0857 1.0000 Uani S T . . .
O11 O 0.19278(15) 0.45406(16) 0.0044(2) 0.0741 1.0000 Uani D U . . .
C12 C 0.2798(4) 0.4845(5) 0.0774(5) 0.0895 0.664(7) Uani D U P 1 1
C13 C 0.2819(5) 0.4319(5) 0.2110(5) 0.1114 0.664(7) Uani D U P 1 1
C14 C 0.3763(5) 0.4582(5) 0.2834(7) 0.1034 0.664(7) Uani D U P 1 1
C112 C 0.2655(7) 0.4203(6) 0.0980(9) 0.0814 0.336(7) Uani D U P 1 2
C113 C 0.3121(8) 0.5077(7) 0.1612(14) 0.1025 0.336(7) Uani D U P 1 2
C114 C 0.4145(8) 0.4826(11) 0.2132(18) 0.1095 0.336(7) Uani D U P 1 2
C901 C 0.000000(9) 0.500000(9) 0.2030(13) 0.0715 0.536(6) Uani S T P 2 1
Cl902 Cl 0.07472(19) 0.57472(19) 0.3023(3) 0.1137 0.536(6) Uani S T P 2 1
H11 H 0.1864 0.6864 -0.0710 0.0725 1.0000 Uiso RS . . . .
H12 H 0.1103 0.6103 -0.0232 0.0719 1.0000 Uiso RS . . . .
H41 H 0.2648 0.5181 -0.4898 0.0799 1.0000 Uiso R . . . .
H51 H 0.2763 0.3620 -0.4106 0.0782 1.0000 Uiso R . . . .
H121 H 0.2725 0.5538 0.0943 0.1082 0.664(7) Uiso R . P 1 1
H122 H 0.3414 0.4692 0.0266 0.1080 0.664(7) Uiso R . P 1 1
H131 H 0.2275 0.4631 0.2594 0.1328 0.664(7) Uiso R . P 1 1
H132 H 0.2698 0.3646 0.2039 0.1330 0.664(7) Uiso R . P 1 1
H141 H 0.3705 0.4379 0.3810 0.1602 0.664(7) Uiso R . P 1 1
H142 H 0.3867 0.5279 0.2769 0.1608 0.664(7) Uiso R . P 1 1
H143 H 0.4258 0.4167 0.2371 0.1611 0.664(7) Uiso R . P 1 1
H1121 H 0.3128 0.3811 0.0470 0.1059 0.336(7) Uiso R . P 1 2
H1122 H 0.2400 0.3843 0.1735 0.1061 0.336(7) Uiso R . P 1 2
H1131 H 0.3235 0.5536 0.0870 0.1252 0.336(7) Uiso R . P 1 2
H1132 H 0.2675 0.5347 0.2284 0.1248 0.336(7) Uiso R . P 1 2
H1143 H 0.4180 0.5077 0.3118 0.1504 0.336(7) Uiso R . P 1 2
H1142 H 0.4675 0.5143 0.1489 0.1500 0.336(7) Uiso R . P 1 2
H1141 H 0.4192 0.4078 0.2076 0.1506 0.336(7) Uiso R . P 1 2
H9011 H -0.0396 0.5396 0.1476 0.0927 0.536(6) Uiso RS . P 2 1
H71 H 0.2538 0.2462 -0.2195 0.0825 1.0000 Uiso RS . . . .
H72 H 0.2184 0.2816 -0.0793 0.0825 1.0000 Uiso RS . . . .
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
C 0.0181 0.0091 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512
0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998
0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
Cl 0.3639 0.7018 11.4604 0.0104 7.1964 1.1662 6.2556 18.5194 1.6455 47.7784
-9.5574 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
O 0.0492 0.0322 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089
0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_site_symmetry_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 8_455 C1 C2 . 109.4(3) yes
C2 8_455 C1 H11 . 110.5 no
C2 . C1 H11 . 110.5 no
C2 8_455 C1 H12 . 109.3 no
C2 . C1 H12 . 109.3 no
H11 . C1 H12 . 107.8 no
C1 . C2 C3 . 119.1(3) yes
C1 . C2 C8 . 121.9(3) yes
C3 . C2 C8 . 118.7(2) yes
C2 . C3 C4 . 119.8(2) yes
C2 . C3 C9 . 119.4(2) yes
C4 . C3 C9 . 120.2(3) yes
C3 . C4 C5 . 120.7(2) yes
C3 . C4 H41 . 120.5 no
C5 . C4 H41 . 118.8 no
C4 . C5 C6 . 119.9(3) yes
C4 . C5 H51 . 119.2 no
C6 . C5 H51 . 120.8 no
C5 . C6 C7 . 119.2(3) yes
C5 . C6 C8 . 118.4(3) yes
C7 . C6 C8 . 121.2(3) yes
C6 . C7 C6 6_555 104.8(3) yes
C6 . C7 H71 . 110.5 no
C6 6_555 C7 H71 . 110.5 no
C6 . C7 H72 . 110.7 no
C6 6_555 C7 H72 . 110.7 no
H71 . C7 H72 . 109.5 no
C6 . C8 C2 . 120.9(2) yes
C6 . C8 O11 . 119.9(2) yes
C2 . C8 O11 . 118.9(2) yes
C3 . C9 C3 8_455 113.7(3) yes
C3 . C9 O10 . 122.87(16) yes
C3 8_455 C9 O10 . 122.87(16) yes
C8 . O11 C12 . 109.0(3) yes
C8 . O11 C112 . 125.7(5) yes
O11 . C12 C13 . 108.0(4) yes
O11 . C12 H121 . 106.3 no
C13 . C12 H121 . 109.0 no
O11 . C12 H122 . 112.8 no
C13 . C12 H122 . 108.5 no
H121 . C12 H122 . 112.1 no
C12 . C13 C14 . 108.1(4) yes
C12 . C13 H131 . 101.5 no
C14 . C13 H131 . 108.6 no
C12 . C13 H132 . 113.8 no
C14 . C13 H132 . 114.6 no
H131 . C13 H132 . 109.3 no
C13 . C14 H141 . 108.2 no
C13 . C14 H142 . 109.2 no
H141 . C14 H142 . 110.4 no
C13 . C14 H143 . 103.5 no
H141 . C14 H143 . 109.5 no
H142 . C14 H143 . 115.7 no
O11 . C112 C113 . 107.8(5) yes
O11 . C112 H1121 . 108.1 no
C113 . C112 H1121 . 111.7 no
O11 . C112 H1122 . 114.0 no
C113 . C112 H1122 . 104.5 no
H1121 . C112 H1122 . 110.7 no
C112 . C113 C114 . 110.5(7) yes
C112 . C113 H1131 . 106.1 no
C114 . C113 H1131 . 104.4 no
C112 . C113 H1132 . 108.5 no
C114 . C113 H1132 . 115.8 no
H1131 . C113 H1132 . 111.1 no
C113 . C114 H1143 . 106.3 no
C113 . C114 H1142 . 109.8 no
H1143 . C114 H1142 . 113.1 no
C113 . C114 H1141 . 105.3 no
H1143 . C114 H1141 . 112.4 no
H1142 . C114 H1141 . 109.6 no
Cl902 6_555 C901 H9011 3_565 108.8 no
Cl902 6_555 C901 Cl902 . 112.2(7) yes
H9011 3_565 C901 Cl902 . 108.8 no
Cl902 6_555 C901 H9011 . 108.8 no
H9011 3_565 C901 H9011 . 109.5 no
Cl902 . C901 H9011 . 108.8 no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 8_455 1.512(3) yes
C1 C2 . 1.512(3) yes
C1 H11 . 0.985 no
C1 H12 . 0.951 no
C2 C3 . 1.401(4) yes
C2 C8 . 1.389(4) yes
C3 C4 . 1.385(4) yes
C3 C9 . 1.482(3) yes
C4 C5 . 1.375(4) yes
C4 H41 . 0.949 no
C5 C6 . 1.404(4) yes
C5 H51 . 0.968 no
C6 C7 . 1.520(3) yes
C6 C8 . 1.396(4) yes
C7 H71 . 0.950 no
C7 H72 . 0.950 no
C8 O11 . 1.379(3) yes
C9 O10 . 1.230(5) yes
O11 C12 . 1.468(4) yes
O11 C112 . 1.447(4) yes
C12 C13 . 1.511(4) yes
C12 H121 . 0.980 no
C12 H122 . 1.013 no
C13 C14 . 1.536(5) yes
C13 H131 . 0.993 no
C13 H132 . 0.950 no
C14 H141 . 1.010 no
C14 H142 . 0.979 no
C14 H143 . 1.005 no
C112 C113 . 1.508(5) yes
C112 H1121 . 0.989 no
C112 H1122 . 0.967 no
C113 C114 . 1.548(5) yes
C113 H1131 . 0.984 no
C113 H1132 . 0.982 no
C114 H1143 . 1.037 no
C114 H1142 . 1.068 no
C114 H1141 . 1.041 no
C901 Cl902 6_555 1.764(8) yes
C901 H9011 3_565 0.950 no
C901 Cl902 . 1.764(8) yes
C901 H9011 . 0.950 no
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_angle_DHA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_publ_flag
C5 H51 O10 4_654 160 0.968 2.481 3.409(7) yes
C901 H9011 O11 3_565 145 0.950 2.555 3.378(7) yes
C901 H9011 O11 8_455 145 0.950 2.555 3.378(7) yes
