#------------------------------------------------------------------------------
#$Date: 2016-03-25 22:51:44 +0200 (Fri, 25 Mar 2016) $
#$Revision: 180017 $
#$URL: svn://www.crystallography.net/cod/cif/7/03/11/7031144.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_7031144
loop_
_publ_author_name
'Desroches, Cedric'
'Lopes, Cesar'
'Kessler, Vadim'
'Parola, Stephane'
_publ_section_title
;
 Design and synthesis of multifunctional thiacalixarenes and related metal
 derivatives for the preparation of sol--gel hybrid materials with
 non-linear optical properties
;
_journal_issue                   10
_journal_name_full               'Dalton Transactions'
_journal_page_first              2085
_journal_page_last               2092
_journal_paper_doi               10.1039/b210252h
_journal_year                    2003
_chemical_formula_sum            'C88 H96 O4 S4'
_chemical_formula_weight         1345.89
_chemical_name_systematic        ?
_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           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 125.796(15)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   23.009(4)
_cell_length_b                   23.370(4)
_cell_length_c                   17.968(3)
_cell_measurement_reflns_used    999(I>2sigma(I))
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      20.0
_cell_measurement_theta_min      1.40
_cell_volume                     7837(3)
_computing_cell_refinement       'Bruker SAINTPLUS'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINTPLUS'
_computing_molecular_graphics    'Bruker SHELXTL-NT'
_computing_publication_material  'Bruker SHELXTL-NT'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type  'Bruker SMART CCD 1k'
_diffrn_measurement_method       'Bruker SMART'
_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  0.0619
_diffrn_reflns_av_sigmaI/netI    0.0598
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            11918
_diffrn_reflns_theta_full        20.00
_diffrn_reflns_theta_max         20.00
_diffrn_reflns_theta_min         1.40
_exptl_absorpt_coefficient_mu    0.170
_exptl_absorpt_correction_T_max  0.9429
_exptl_absorpt_correction_T_min  0.8220
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.141
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             2880
_exptl_crystal_size_max          1.20
_exptl_crystal_size_mid          1.00
_exptl_crystal_size_min          0.35
_refine_diff_density_max         0.380
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       0.00021(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     433
_refine_ls_number_reflns         3654
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.1195
_refine_ls_R_factor_gt           0.0595
_refine_ls_shift/su_max          0.018
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0965P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1514
_refine_ls_wR_factor_ref         0.1702
_reflns_number_gt                2045
_reflns_number_total             3654
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b210252h.txt
_cod_data_source_block           calix1tm
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/automatic-downloads/retrospective/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from
2011-04-26.

'_exptl_absorpt_correction_type' value 'Empirical'
changed to 'empirical' according to
/usr/data/users/saulius/automatic-downloads/retrospective/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 2281 2013-09-26 08:29:07Z andrius 
;
_cod_original_cell_volume        7837(2)
_cod_original_sg_symbol_H-M      C2/c
_cod_database_code               7031144
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_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
S1 S 0.70634(8) 0.14886(6) 0.96347(10) 0.0788(5) Uani 1 1 d .
S2 S 0.55451(9) 0.15080(6) 0.58353(10) 0.0811(6) Uani 1 1 d .
O1 O 0.43469(19) 0.09734(16) 0.5859(2) 0.0756(11) Uani 1 1 d .
O2 O 0.6122(2) 0.20252(16) 0.7712(2) 0.0801(12) Uani 1 1 d .
C201 C 0.6272(3) 0.1459(2) 0.7728(4) 0.0623(14) Uani 1 1 d .
C202 C 0.6676(3) 0.1158(2) 0.8558(4) 0.0612(15) Uani 1 1 d .
C102 C 0.6410(3) 0.2410(2) 0.9699(3) 0.0708(16) Uani 1 1 d .
H10A H 0.6821 0.2599 0.9848 0.085 Uiso 1 1 calc R
C205 C 0.6579(3) 0.0293(2) 0.7750(5) 0.0764(17) Uani 1 1 d .
C203 C 0.6166(3) 0.0596(3) 0.6934(4) 0.0763(16) Uani 1 1 d .
H20A H 0.5993 0.0407 0.6386 0.092 Uiso 1 1 calc R
C204 C 0.6002(3) 0.1171(2) 0.6905(4) 0.0650(15) Uani 1 1 d .
C117 C 0.4267(4) 0.1551(2) 0.5660(3) 0.0643(14) Uani 1 1 d .
C8 C 0.6827(3) 0.0588(2) 0.8554(4) 0.0726(16) Uani 1 1 d .
H8A H 0.7105 0.0394 0.9110 0.087 Uiso 1 1 calc R
C118 C 0.4813(3) 0.1851(2) 0.5703(3) 0.0627(15) Uani 1 1 d .
C105 C 0.5816(5) 0.4449(3) 0.9775(7) 0.096(2) Uani 1 1 d .
C101 C 0.6339(3) 0.1835(2) 0.9529(3) 0.0620(15) Uani 1 1 d .
C111 C 0.5616(5) 0.5618(3) 0.9743(8) 0.108(2) Uani 1 1 d .
C119 C 0.4732(3) 0.2430(2) 0.5540(3) 0.0729(16) Uani 1 1 d .
H119 H 0.5088 0.2634 0.5559 0.087 Uiso 1 1 calc R
C110 C 0.5150(4) 0.5283(4) 0.9015(7) 0.153(3) Uani 1 1 d .
H11E H 0.4751 0.5449 0.8493 0.184 Uiso 1 1 calc R
C209 C 0.7352(4) -0.1685(3) 0.8549(6) 0.121(2) Uani 1 1 d .
H20B H 0.7627 -0.1480 0.9095 0.146 Uiso 1 1 calc R
C103 C 0.5869(4) 0.2717(2) 0.9652(3) 0.0718(16) Uani 1 1 d .
C109 C 0.6194(5) 0.5352(4) 1.0489(6) 0.116(2) Uani 1 1 d .
H10D H 0.6530 0.5571 1.0995 0.139 Uiso 1 1 calc R
C104 C 0.5906(3) 0.3338(3) 0.9768(4) 0.0858(19) Uani 1 1 d .
C114 C 0.5583(4) 0.7239(2) 0.9160(5) 0.114(2) Uani 1 1 d .
H11F H 0.5075 0.7321 0.8819 0.137 Uiso 1 1 calc R
H11G H 0.5808 0.7362 0.9788 0.137 Uiso 1 1 calc R
C107 C 0.6292(4) 0.4779(3) 1.0515(5) 0.107(2) Uani 1 1 d .
H10E H 0.6686 0.4610 1.1038 0.128 Uiso 1 1 calc R
C208 C 0.6863(4) -0.1406(3) 0.7759(5) 0.0846(18) Uani 1 1 d .
C112 C 0.5478(4) 0.6258(3) 0.9680(6) 0.137(3) Uani 1 1 d .
H11H H 0.4972 0.6318 0.9396 0.164 Uiso 1 1 calc R
H11I H 0.5740 0.6411 1.0297 0.164 Uiso 1 1 calc R
C210 C 0.6460(4) -0.1733(3) 0.6988(5) 0.102(2) Uani 1 1 d .
H21A H 0.6113 -0.1557 0.6436 0.122 Uiso 1 1 calc R
C401 C 0.6657(4) 0.2404(2) 0.7798(5) 0.123(3) Uani 1 1 d .
C214 C 0.7167(5) -0.3245(3) 0.7806(6) 0.150(3) Uani 1 1 d .
H21B H 0.6938 -0.3378 0.7182 0.180 Uiso 1 1 calc R
H21C H 0.7676 -0.3318 0.8139 0.180 Uiso 1 1 calc R
C206 C 0.6702(3) -0.0310(3) 0.7756(4) 0.0872(19) Uani 1 1 d .
C207 C 0.6771(3) -0.0807(3) 0.7751(4) 0.0856(19) Uani 1 1 d .
C108 C 0.5255(5) 0.4705(4) 0.9032(7) 0.152(3) Uani 1 1 d .
H10F H 0.4931 0.4486 0.8517 0.182 Uiso 1 1 calc R
C113 C 0.5681(4) 0.6589(2) 0.9154(5) 0.112(2) Uani 1 1 d .
H11J H 0.5394 0.6456 0.8523 0.134 Uiso 1 1 calc R
H11K H 0.6179 0.6510 0.9410 0.134 Uiso 1 1 calc R
C106 C 0.5893(4) 0.3847(3) 0.9799(5) 0.100(2) Uani 1 1 d .
C215 C 0.6908(5) -0.3573(3) 0.8205(6) 0.158(3) Uani 1 1 d .
H21C' H 0.6399 -0.3502 0.7883 0.189 Uiso 1 1 calc R
H21D H 0.7145 -0.3454 0.8838 0.189 Uiso 1 1 calc R
C213 C 0.7053(5) -0.2593(3) 0.7781(7) 0.104(2) Uani 1 1 d .
C211 C 0.7450(4) -0.2278(3) 0.8555(6) 0.127(3) Uani 1 1 d .
H21E H 0.7796 -0.2458 0.9104 0.153 Uiso 1 1 calc R
C212 C 0.6551(5) -0.2317(3) 0.7000(5) 0.110(2) Uani 1 1 d .
H21F H 0.6260 -0.2525 0.6460 0.132 Uiso 1 1 calc R
C115 C 0.5879(4) 0.7575(3) 0.8767(5) 0.133(3) Uani 1 1 d .
H11L H 0.5639 0.7468 0.8129 0.160 Uiso 1 1 calc R
H11M H 0.6384 0.7486 0.9091 0.160 Uiso 1 1 calc R
C216 C 0.7028(5) -0.4209(3) 0.8181(7) 0.168(4) Uani 1 1 d .
H21G H 0.6764 -0.4335 0.7548 0.201 Uiso 1 1 calc R
H21H H 0.7533 -0.4279 0.8469 0.201 Uiso 1 1 calc R
C116 C 0.5794(5) 0.8211(3) 0.8824(6) 0.171(4) Uani 1 1 d .
H11N H 0.5996 0.8414 0.8562 0.256 Uiso 1 1 calc R
H11O H 0.6037 0.8320 0.9455 0.256 Uiso 1 1 calc R
H11P H 0.5294 0.8303 0.8492 0.256 Uiso 1 1 calc R
C303 C 0.4553(6) -0.0228(4) 0.6162(9) 0.237(6) Uani 1 1 d .
H30A H 0.4466 -0.0631 0.6137 0.356 Uiso 1 1 calc R
H30B H 0.4509 -0.0054 0.6611 0.356 Uiso 1 1 calc R
H30C H 0.5028 -0.0165 0.6328 0.356 Uiso 1 1 calc R
C302 C 0.4079(6) 0.0003(4) 0.5347(7) 0.170(4) Uani 1 1 d .
H30D H 0.3743 -0.0245 0.4890 0.204 Uiso 1 1 calc R
C301 C 0.4026(4) 0.0595(3) 0.5090(5) 0.119(2) Uani 1 1 d .
H30E H 0.3524 0.0695 0.4656 0.143 Uiso 1 1 calc R
H30F H 0.4258 0.0646 0.4785 0.143 Uiso 1 1 calc R
C218 C 0.6808(5) -0.5151(4) 0.8519(7) 0.218(5) Uani 1 1 d .
H21I H 0.6650 -0.5346 0.8842 0.327 Uiso 1 1 calc R
H21J H 0.7285 -0.5271 0.8755 0.327 Uiso 1 1 calc R
H21K H 0.6492 -0.5241 0.7877 0.327 Uiso 1 1 calc R
C217 C 0.6802(6) -0.4531(3) 0.8647(8) 0.199(5) Uani 1 1 d .
H21L H 0.6321 -0.4414 0.8422 0.239 Uiso 1 1 calc R
H21M H 0.7115 -0.4444 0.9297 0.239 Uiso 1 1 calc R
C402 C 0.6234(16) 0.3055(11) 0.7655(17) 0.159(10) Uiso 0.58(2) 1 d P
C403 C 0.6729(8) 0.3425(6) 0.7677(9) 0.138(8) Uiso 0.58(2) 1 d P
C40A C 0.6560(13) 0.2934(11) 0.7846(14) 0.106(10) Uiso 0.42(2) 1 d P
C40B C 0.5940(15) 0.3222(11) 0.7599(17) 0.147(11) Uiso 0.42(2) 1 d P
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'
S S 0.1246 0.1234 '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
C202 S1 C101 104.1(3) . .
C118 S2 C204 105.5(2) . .
C117 O1 C301 116.0(4) . .
C201 O2 C401 113.8(4) . .
O2 C201 C204 119.6(5) . .
O2 C201 C202 120.9(5) . .
C204 C201 C202 119.5(5) . .
C8 C202 C201 119.5(5) . .
C8 C202 S1 117.5(5) . .
C201 C202 S1 122.8(4) . .
C101 C102 C103 120.4(5) . .
C8 C205 C203 117.3(5) . .
C8 C205 C206 121.4(6) . .
C203 C205 C206 121.2(6) . .
C205 C203 C204 122.5(5) . .
C201 C204 C203 118.9(5) . .
C201 C204 S2 123.8(4) . .
C203 C204 S2 117.0(5) . .
O1 C117 C118 119.7(5) . .
O1 C117 C101 119.4(5) . 2_656
C118 C117 C101 120.8(5) . 2_656
C202 C8 C205 122.3(5) . .
C119 C118 C117 118.4(5) . .
C119 C118 S2 118.6(5) . .
C117 C118 S2 122.6(5) . .
C108 C105 C107 118.4(6) . .
C108 C105 C106 120.4(8) . .
C107 C105 C106 121.2(8) . .
C102 C101 C117 119.6(5) . 2_656
C102 C101 S1 116.5(5) . .
C117 C101 S1 123.8(4) 2_656 .
C109 C111 C110 116.7(7) . .
C109 C111 C112 124.3(9) . .
C110 C111 C112 119.0(10) . .
C118 C119 C103 121.3(5) . 2_656
C111 C110 C108 121.3(8) . .
C208 C209 C211 121.0(7) . .
C102 C103 C119 119.5(5) . 2_656
C102 C103 C104 121.7(6) . .
C119 C103 C104 118.8(6) 2_656 .
C111 C109 C107 122.1(7) . .
C106 C104 C103 175.2(7) . .
C115 C114 C113 114.6(6) . .
C105 C107 C109 120.2(7) . .
C209 C208 C210 116.6(6) . .
C209 C208 C207 121.0(7) . .
C210 C208 C207 122.4(7) . .
C113 C112 C111 115.4(6) . .
C208 C210 C212 122.1(7) . .
C40A C401 O2 115.6(11) . .
C40A C401 C402 18.9(16) . .
O2 C401 C402 98.7(10) . .
C215 C214 C213 116.2(6) . .
C207 C206 C205 176.8(7) . .
C206 C207 C208 179.1(9) . .
C105 C108 C110 121.2(8) . .
C112 C113 C114 114.0(5) . .
C104 C106 C105 175.3(8) . .
C214 C215 C216 112.4(7) . .
C211 C213 C212 117.5(7) . .
C211 C213 C214 120.5(9) . .
C212 C213 C214 122.0(8) . .
C213 C211 C209 121.5(7) . .
C213 C212 C210 121.3(7) . .
C114 C115 C116 112.3(6) . .
C217 C216 C215 111.3(7) . .
C303 C302 C301 127.2(9) . .
C302 C301 O1 112.6(6) . .
C216 C217 C218 112.8(9) . .
C40A C402 C40B 162(7) . .
C40A C402 C403 67(4) . .
C40B C402 C403 110(4) . .
C40A C402 C401 37(3) . .
C40B C402 C401 151(4) . .
C403 C402 C401 99.1(19) . .
C40A C403 C402 28.5(16) . .
C40A C403 C40B 50.3(18) . .
C402 C403 C40B 22.5(14) . .
C402 C40A C403 85(4) . .
C402 C40A C401 124(4) . .
C403 C40A C401 139(2) . .
C402 C40A C40B 10(3) . .
C403 C40A C40B 83.7(17) . .
C401 C40A C40B 129.6(17) . .
C402 C40B C40A 9(3) . .
C402 C40B C403 48(3) . .
C40A C40B C403 46.0(11) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 C202 1.766(5) .
S1 C101 1.760(5) .
S2 C118 1.751(5) .
S2 C204 1.748(5) .
O1 C117 1.380(5) .
O1 C301 1.429(6) .
O2 C201 1.364(5) .
O2 C401 1.448(6) .
C201 C204 1.398(6) .
C201 C202 1.400(6) .
C202 C8 1.378(6) .
C102 C101 1.369(6) .
C102 C103 1.395(7) .
C205 C8 1.385(7) .
C205 C203 1.387(7) .
C205 C206 1.437(7) .
C203 C204 1.387(6) .
C117 C118 1.402(7) .
C117 C101 1.394(6) 2_656
C118 C119 1.375(6) .
C105 C108 1.338(9) .
C105 C107 1.363(8) .
C105 C106 1.415(8) .
C101 C117 1.394(6) 2_656
C111 C109 1.367(9) .
C111 C110 1.354(9) .
C111 C112 1.517(8) .
C119 C103 1.387(7) 2_656
C110 C108 1.370(8) .
C209 C208 1.356(8) .
C209 C211 1.403(8) .
C103 C119 1.387(7) 2_656
C103 C104 1.462(7) .
C109 C107 1.355(8) .
C104 C106 1.192(8) .
C114 C115 1.463(7) .
C114 C113 1.537(7) .
C208 C210 1.365(8) .
C208 C207 1.414(7) .
C112 C113 1.493(8) .
C210 C212 1.378(7) .
C401 C40A 1.27(2) .
C401 C402 1.74(3) .
C214 C215 1.399(8) .
C214 C213 1.543(8) .
C206 C207 1.173(7) .
C215 C216 1.516(8) .
C213 C211 1.351(9) .
C213 C212 1.351(9) .
C115 C116 1.510(7) .
C216 C217 1.431(11) .
C303 C302 1.325(12) .
C302 C301 1.442(9) .
C218 C217 1.468(9) .
C402 C40A 0.68(4) .
C402 C40B 0.73(4) .
C402 C403 1.41(3) .
C403 C40A 1.30(2) .
C403 C40B 1.80(3) .
C40A C40B 1.39(4) .
