#------------------------------------------------------------------------------
#$Date: 2015-06-17 10:04:54 +0300 (Wed, 17 Jun 2015) $
#$Revision: 139285 $
#$URL: svn://www.crystallography.net/cod/cif/7/22/07/7220783.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_7220783
loop_
_publ_author_name
'Rahman, Shofiur'
'Zein, Ahmed'
'Dawe, Louise N.'
'Shamov, Grigory'
'Thordarson, Pall'
'Georghiou, Paris Elias'
_publ_section_title
;
 Supramolecular host-guest complexation of Lash's calix[4]azulene with
 tetraalkylammonium salts: binding and DFT computational studies
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C5RA07802D
_journal_year                    2015
_chemical_formula_moiety         'C44 H32'
_chemical_formula_sum            'C44 H32'
_chemical_formula_weight         560.69
_chemical_name_systematic
;
 ?
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_date             2015-02-16
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_audit_update_record
;
2015-02-16 deposited with the CCDC.
2015-06-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 97.075(8)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   21.779(11)
_cell_length_b                   4.904(2)
_cell_length_c                   27.269(12)
_cell_measurement_reflns_used    5409
_cell_measurement_temperature    153(2)
_cell_measurement_theta_max      30.7132
_cell_measurement_theta_min      2.5529
_cell_volume                     2890(2)
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL-2014 (Sheldrick, 2008)'
_computing_structure_solution
;
ShelXS-97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      153(2)
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details
;
scan:
    Number of images: 360
               Slice: -75.0000 - 105.0000
         Image width: 0.5000
            Exp time: 35.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 45.0000
                 Phi: 90.0000
                 XTD: 40.0573
              2theta: 15.0966
scan:
    Number of images: 360
               Slice: -75.0000 - 105.0000
         Image width: 0.5000
            Exp time: 35.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 0.0000
                 Phi: 0.0000
                 XTD: 40.0573
              2theta: 15.0966
scan:
    Number of images: 286
               Slice: -40.0000 - 103.0000
         Image width: 0.5000
            Exp time: 35.0000
       Rotation axis: Omega
               Omega: 0.0000
                 Chi: 45.0000
                 Phi: 0.0000
                 XTD: 40.0573
              2theta: 15.0966
;
_diffrn_measurement_device
;
Saturn70 (2x2 bin mode)
;
_diffrn_measurement_device_details
;
AFC8: Eulerian 3 circle
;
_diffrn_measurement_device_type  'Rigaku Saturn'
_diffrn_measurement_method       dtprofit.ref
_diffrn_orient_matrix_type       d*Trek
_diffrn_orient_matrix_UB_11      0.0364
_diffrn_orient_matrix_UB_12      0.0068
_diffrn_orient_matrix_UB_13      0.0277
_diffrn_orient_matrix_UB_21      -0.1254
_diffrn_orient_matrix_UB_22      0.0520
_diffrn_orient_matrix_UB_23      0.1521
_diffrn_orient_matrix_UB_31      0.0020
_diffrn_orient_matrix_UB_32      -0.0344
_diffrn_orient_matrix_UB_33      0.0134
_diffrn_radiation_detector       CCD
_diffrn_radiation_monochromator  Other
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71075
_diffrn_reflns_av_R_equivalents  0.0484
_diffrn_reflns_av_unetI/netI     0.0321
_diffrn_reflns_laue_measured_fraction_full 0.998
_diffrn_reflns_laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -34
_diffrn_reflns_number            16217
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.492
_diffrn_reflns_theta_min         2.553
_diffrn_source                   'Sealed Tube'
_diffrn_source_current           40.0000
_diffrn_source_power             2.0000
_diffrn_source_voltage           50.0000
_exptl_absorpt_coefficient_mu    0.073
_exptl_absorpt_correction_T_max  0.9975
_exptl_absorpt_correction_T_min  0.9849
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details   '(T. Higashi, 2000)'
_exptl_crystal_colour            Green
_exptl_crystal_density_diffrn    1.288
_exptl_crystal_description       Platelet
_exptl_crystal_F_000             1184
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.188
_refine_diff_density_min         -0.191
_refine_diff_density_rms         0.041
_refine_ls_extinction_coef       0.0008(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.179
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2982
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.179
_refine_ls_R_factor_all          0.0751
_refine_ls_R_factor_gt           0.0658
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0410P)²+3.3521P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1361
_refine_ls_wR_factor_ref         0.1415
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2647
_reflns_number_total             2982
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c5ra07802d4.cif
_cod_data_source_block           shelxl
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_absorpt_correction_type' value 'Numerical' changed to
'numerical' according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 3271 2015-04-21 07:52:19Z andrius 
;
_cod_original_cell_volume        2891(2)
_cod_database_code               7220783
_shelxl_version_number           2013-4
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_max   0.997
_shelx_estimated_absorpt_t_min   0.976
_diffrn_number_total             4591
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C22(H22A,H22B)
2.b Aromatic/amide H refined with riding coordinates:
 C1(H1), C4(H4), C5(H5), C6(H6), C7(H7), C8(H8), C14(H14), C15(H15), C16(H16),
 C17(H17), C18(H18), C21(H21)
;
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_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_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
C1 C 0.32512(9) 1.1352(4) 0.54095(7) 0.0350(5) Uani 1 1 d .
H1 H 0.3007 1.2734 0.5255 0.042 Uiso 1 1 calc R
C2 C 0.37415(9) 1.0107(4) 0.52107(7) 0.0336(5) Uani 1 1 d .
C3 C 0.40002(9) 0.8161(4) 0.55551(7) 0.0327(4) Uani 1 1 d .
C4 C 0.44937(9) 0.6447(4) 0.55050(7) 0.0376(5) Uani 1 1 d .
H4 H 0.4660 0.6600 0.5208 0.045 Uiso 1 1 calc R
C5 C 0.47767(10) 0.4538(5) 0.58326(8) 0.0421(5) Uani 1 1 d .
H5 H 0.5105 0.3597 0.5724 0.050 Uiso 1 1 calc R
C6 C 0.46397(10) 0.3834(5) 0.62987(8) 0.0443(5) Uani 1 1 d .
H6 H 0.4893 0.2503 0.6460 0.053 Uiso 1 1 calc R
C7 C 0.41790(10) 0.4823(5) 0.65613(8) 0.0449(5) Uani 1 1 d .
H7 H 0.4173 0.4100 0.6876 0.054 Uiso 1 1 calc R
C8 C 0.37257(10) 0.6758(4) 0.64135(7) 0.0370(5) Uani 1 1 d .
H8 H 0.3444 0.7080 0.6637 0.044 Uiso 1 1 calc R
C9 C 0.36329(9) 0.8266(4) 0.59839(7) 0.0324(4) Uani 1 1 d .
C10 C 0.31742(9) 1.0260(4) 0.58688(7) 0.0333(5) Uani 1 1 d .
C11 C 0.26662(9) 1.0977(4) 0.61738(7) 0.0371(5) Uani 1 1 d .
H11A H 0.2503 1.2765 0.6078 0.045 Uiso 1 1 calc R
H11B H 0.2834 1.1052 0.6520 0.045 Uiso 1 1 calc R
C12 C 0.21510(9) 0.8901(4) 0.61040(7) 0.0332(5) Uani 1 1 d .
C13 C 0.18345(9) 0.7712(4) 0.64672(7) 0.0341(5) Uani 1 1 d .
C14 C 0.19272(10) 0.8262(5) 0.69715(7) 0.0404(5) Uani 1 1 d .
H14 H 0.2233 0.9541 0.7071 0.049 Uiso 1 1 calc R
C15 C 0.16280(10) 0.7171(5) 0.73452(7) 0.0455(6) Uani 1 1 d .
H15 H 0.1754 0.7850 0.7660 0.055 Uiso 1 1 calc R
C16 C 0.11662(11) 0.5205(5) 0.73172(8) 0.0484(6) Uani 1 1 d .
H16 H 0.1029 0.4754 0.7617 0.058 Uiso 1 1 calc R
C17 C 0.08803(11) 0.3819(5) 0.69100(8) 0.0460(6) Uani 1 1 d .
H17 H 0.0586 0.2536 0.6975 0.055 Uiso 1 1 calc R
C18 C 0.09725(10) 0.4084(5) 0.64153(8) 0.0393(5) Uani 1 1 d .
H18 H 0.0728 0.2967 0.6195 0.047 Uiso 1 1 calc R
C19 C 0.13750(9) 0.5769(4) 0.62068(7) 0.0336(5) Uani 1 1 d .
C20 C 0.14346(9) 0.5929(4) 0.56975(7) 0.0326(4) Uani 1 1 d .
C21 C 0.19027(9) 0.7802(4) 0.56461(7) 0.0335(5) Uani 1 1 d .
H21 H 0.2035 0.8268 0.5346 0.040 Uiso 1 1 calc R
C22 C 0.10720(9) 0.4314(5) 0.52896(7) 0.0379(5) Uani 1 1 d .
H22A H 0.1128 0.2385 0.5360 0.046 Uiso 1 1 calc R
H22B H 0.0636 0.4724 0.5285 0.046 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'
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_1
_geom_angle_site_symmetry_3
C2 C1 H1 124.3 . .
C10 C1 H1 124.3 . .
C10 C1 C2 111.35(19) . .
C1 C2 C3 107.46(17) . .
C1 C2 C22 125.23(19) . 7_566
C3 C2 C22 127.25(19) . 7_566
C2 C3 C9 106.82(17) . .
C4 C3 C2 126.73(18) . .
C4 C3 C9 126.45(19) . .
C3 C4 H4 115.3 . .
C3 C4 C5 129.5(2) . .
C5 C4 H4 115.3 . .
C4 C5 H5 115.4 . .
C6 C5 C4 129.2(2) . .
C6 C5 H5 115.4 . .
C5 C6 H6 115.2 . .
C5 C6 C7 129.6(2) . .
C7 C6 H6 115.2 . .
C6 C7 H7 115.9 . .
C6 C7 C8 128.3(2) . .
C8 C7 H7 115.9 . .
C7 C8 H8 115.3 . .
C9 C8 C7 129.5(2) . .
C9 C8 H8 115.3 . .
C8 C9 C3 127.49(19) . .
C8 C9 C10 126.05(18) . .
C10 C9 C3 106.45(17) . .
C1 C10 C9 107.91(17) . .
C1 C10 C11 125.86(19) . .
C9 C10 C11 126.14(18) . .
C10 C11 H11A 109.4 . .
C10 C11 H11B 109.4 . .
C10 C11 C12 110.99(17) . .
H11A C11 H11B 108.0 . .
C12 C11 H11A 109.4 . .
C12 C11 H11B 109.4 . .
C13 C12 C11 127.88(18) . .
C13 C12 C21 107.42(18) . .
C21 C12 C11 124.70(18) . .
C12 C13 C19 106.74(16) . .
C14 C13 C12 126.4(2) . .
C14 C13 C19 126.84(19) . .
C13 C14 H14 115.5 . .
C15 C14 C13 129.0(2) . .
C15 C14 H14 115.5 . .
C14 C15 H15 115.4 . .
C14 C15 C16 129.2(2) . .
C16 C15 H15 115.4 . .
C15 C16 H16 115.2 . .
C17 C16 C15 129.6(2) . .
C17 C16 H16 115.2 . .
C16 C17 H17 115.6 . .
C16 C17 C18 128.8(2) . .
C18 C17 H17 115.6 . .
C17 C18 H18 115.5 . .
C19 C18 C17 129.1(2) . .
C19 C18 H18 115.5 . .
C18 C19 C13 127.50(18) . .
C18 C19 C20 125.4(2) . .
C20 C19 C13 107.10(17) . .
C19 C20 C22 126.37(18) . .
C21 C20 C19 107.02(17) . .
C21 C20 C22 126.59(18) . .
C12 C21 H21 124.1 . .
C20 C21 C12 111.71(18) . .
C20 C21 H21 124.1 . .
C2 C22 C20 113.35(17) 7_566 .
C2 C22 H22A 108.9 7_566 .
C2 C22 H22B 108.9 7_566 .
C20 C22 H22A 108.9 . .
C20 C22 H22B 108.9 . .
H22A C22 H22B 107.7 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
C1 H1 0.9300 .
C1 C2 1.396(3) .
C1 C10 1.391(3) .
C2 C3 1.407(3) .
C2 C22 1.498(3) 7_566
C3 C4 1.384(3) .
C3 C9 1.497(3) .
C4 H4 0.9300 .
C4 C5 1.385(3) .
C5 H5 0.9300 .
C5 C6 1.385(3) .
C6 H6 0.9300 .
C6 C7 1.390(3) .
C7 H7 0.9300 .
C7 C8 1.393(3) .
C8 H8 0.9300 .
C8 C9 1.379(3) .
C9 C10 1.406(3) .
C10 C11 1.505(3) .
C11 H11A 0.9700 .
C11 H11B 0.9700 .
C11 C12 1.510(3) .
C12 C13 1.401(3) .
C12 C21 1.406(3) .
C13 C14 1.392(3) .
C13 C19 1.496(3) .
C14 H14 0.9300 .
C14 C15 1.383(3) .
C15 H15 0.9300 .
C15 C16 1.388(4) .
C16 H16 0.9300 .
C16 C17 1.383(3) .
C17 H17 0.9300 .
C17 C18 1.394(3) .
C18 H18 0.9300 .
C18 C19 1.378(3) .
C19 C20 1.413(3) .
C20 C21 1.392(3) .
C20 C22 1.507(3) .
C21 H21 0.9300 .
C22 C2 1.498(3) 7_566
C22 H22A 0.9700 .
C22 H22B 0.9700 .
loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_4
C1 C2 C3 C4 179.47(19) . .
C1 C2 C3 C9 0.3(2) . .
C1 C10 C11 C12 98.1(2) . .
C2 C1 C10 C9 1.1(2) . .
C2 C1 C10 C11 -175.66(18) . .
C2 C3 C4 C5 178.5(2) . .
C2 C3 C9 C8 -178.63(19) . .
C2 C3 C9 C10 0.3(2) . .
C3 C4 C5 C6 0.1(4) . .
C3 C9 C10 C1 -0.8(2) . .
C3 C9 C10 C11 175.91(18) . .
C4 C3 C9 C8 2.2(3) . .
C4 C3 C9 C10 -178.85(19) . .
C4 C5 C6 C7 0.8(4) . .
C5 C6 C7 C8 1.5(4) . .
C6 C7 C8 C9 -3.2(4) . .
C7 C8 C9 C3 1.1(4) . .
C7 C8 C9 C10 -177.6(2) . .
C8 C9 C10 C1 178.14(19) . .
C8 C9 C10 C11 -5.1(3) . .
C9 C3 C4 C5 -2.5(3) . .
C9 C10 C11 C12 -78.1(2) . .
C10 C1 C2 C3 -0.9(2) . .
C10 C1 C2 C22 176.48(18) . 7_566
C10 C11 C12 C13 136.2(2) . .
C10 C11 C12 C21 -43.6(3) . .
C11 C12 C13 C14 1.3(3) . .
C11 C12 C13 C19 -179.29(18) . .
C11 C12 C21 C20 179.79(18) . .
C12 C13 C14 C15 179.6(2) . .
C12 C13 C19 C18 178.1(2) . .
C12 C13 C19 C20 -0.9(2) . .
C13 C12 C21 C20 -0.1(2) . .
C13 C14 C15 C16 1.4(4) . .
C13 C19 C20 C21 0.8(2) . .
C13 C19 C20 C22 179.19(19) . .
C14 C13 C19 C18 -2.6(3) . .
C14 C13 C19 C20 178.5(2) . .
C14 C15 C16 C17 -0.2(4) . .
C15 C16 C17 C18 -1.6(4) . .
C16 C17 C18 C19 0.7(4) . .
C17 C18 C19 C13 2.0(4) . .
C17 C18 C19 C20 -179.3(2) . .
C18 C19 C20 C21 -178.14(19) . .
C18 C19 C20 C22 0.2(3) . .
C19 C13 C14 C15 0.3(4) . .
C19 C20 C21 C12 -0.5(2) . .
C19 C20 C22 C2 -178.22(19) . 7_566
C21 C12 C13 C14 -178.79(19) . .
C21 C12 C13 C19 0.6(2) . .
C21 C20 C22 C2 -0.2(3) . 7_566
C22 C2 C3 C4 2.2(3) 7_566 .
C22 C2 C3 C9 -176.95(18) 7_566 .
C22 C20 C21 C12 -178.85(19) . .
