#------------------------------------------------------------------------------
#$Date: 2016-02-19 16:29:56 +0200 (Fri, 19 Feb 2016) $
#$Revision: 176759 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/84/2008447.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_2008447
loop_
_publ_author_name
'Dix, Ina'
'Hopf, Henning'
'Jones, Peter G.'
_publ_section_title
;
 Heterocycle-substituted [2.2]paracyclophanes
;
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              756
_journal_page_last               759
_journal_paper_doi               10.1107/S0108270199001808
_journal_volume                  55
_journal_year                    1999
_chemical_formula_sum            'C20 H18 S'
_chemical_formula_weight         290.40
_chemical_name_systematic
;
 4-(2'-thienyl)[2.2]paracyclophane
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 95.523(11)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   16.850(2)
_cell_length_b                   7.6203(10)
_cell_length_c                   11.574(2)
_cell_measurement_reflns_used    63
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      11.4
_cell_measurement_theta_min      5.2
_cell_volume                     1479.2(4)
_computing_cell_refinement       XSCANS
_computing_data_collection       'XSCANS (Fait, 1991)'
_computing_data_reduction        XSCANS
_computing_molecular_graphics    'XP (Siemens, 1994)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Siemens P4'
_diffrn_measurement_method       ω-scans
_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  0.0148
_diffrn_reflns_av_sigmaI/netI    0.0601
_diffrn_reflns_limit_h_max       1
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            2773
_diffrn_reflns_theta_full        24.99
_diffrn_reflns_theta_max         24.99
_diffrn_reflns_theta_min         3.21
_diffrn_standards_decay_%        1
_diffrn_standards_interval_count 247
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.209
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.304
_exptl_crystal_density_meas      ?
_exptl_crystal_description       tablet
_exptl_crystal_F_000             616
_exptl_crystal_size_max          0.86
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.182
_refine_diff_density_min         -0.155
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.862
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     227
_refine_ls_number_reflns         2590
_refine_ls_number_restraints     301
_refine_ls_restrained_S_all      0.819
_refine_ls_R_factor_all          0.0708
_refine_ls_R_factor_gt           0.0378
_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)+(0.0418P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0841
_reflns_number_gt                1641
_reflns_number_total             2590
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bm1314.cif
_cod_data_source_block           2
_cod_depositor_comments
;
The following automatic conversions were performed:
'_geom_bond_publ_flag' value 'Y' changed to 'y' according to
'/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_geom_bond_publ_flag' value 'Y' changed to 'y' according to
/home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named
'cif_core.dic' version 2.4.1 from
2010-06-29.

'_geom_torsion_publ_flag' value 'Y' changed to 'y'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29 (3
times).

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 

The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'not measured' was changed to '?'
- the value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 
;
_cod_original_cell_volume        1479.3(4)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2008447
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, 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_disorder_assembly
_atom_site_disorder_group
_atom_site_type_symbol
C1 .32632(13) .7537(3) .57445(19) .0474(6) Uani d U 1 . . C
H1A .3768 .7726 .6241 .057 Uiso calc R 1 . . H
H1B .3141 .8627 .5298 .057 Uiso calc R 1 . . H
C2 .33842(12) .5995(2) .48709(16) .0342(5) Uani d U 1 . . C
H2A .3372 .6481 .4076 .041 Uiso calc R 1 . . H
H2B .3916 .5466 .5070 .041 Uiso calc R 1 . . H
C3 .27540(11) .4572(2) .48846(15) .0271(4) Uani d U 1 . . C
C4 .28385(11) .3099(2) .56260(14) .0245(4) Uani d U 1 A . C
C5 .21499(11) .2348(2) .60022(16) .0291(4) Uani d U 1 . . C
H5 .2204 .1372 .6515 .035 Uiso calc R 1 . . H
C6 .13911(11) .2974(2) .56554(17) .0325(5) Uani d U 1 . . C
C7 .13239(12) .4142(3) .47262(16) .0352(5) Uani d U 1 . . C
H7 .0813 .4407 .4347 .042 Uiso calc R 1 . . H
C8 .19947(11) .4921(2) .43498(15) .0323(5) Uani d U 1 . . C
H8 .1936 .5710 .3712 .039 Uiso calc R 1 . . H
C9 .07093(12) .2672(3) .6391(2) .0466(6) Uani d U 1 . . C
H9A .0767 .1493 .6748 .056 Uiso calc R 1 . . H
H9B .0202 .2689 .5883 .056 Uiso calc R 1 . . H
C10 .06645(12) .4089(3) .73869(17) .0432(5) Uani d U 1 . . C
H10A .0131 .4647 .7304 .052 Uiso calc R 1 . . H
H10B .0731 .3494 .8151 .052 Uiso calc R 1 . . H
C11 .12959(12) .5492(3) .73524(16) .0336(5) Uani d U 1 . . C
C12 .11842(12) .6916(3) .66072(17) .0366(5) Uani d U 1 . . C
H12 .0659 .7321 .6381 .044 Uiso calc R 1 . . H
C13 .18273(13) .7757(3) .61887(17) .0376(5) Uani d U 1 . . C
H13 .1738 .8724 .5675 .045 Uiso calc R 1 . . H
C14 .26017(12) .7197(3) .65144(17) .0358(5) Uani d U 1 . . C
C15 .27103(12) .6039(3) .74405(16) .0359(5) Uani d U 1 . . C
H15 .3233 .5823 .7795 .043 Uiso calc R 1 . . H
C16 .20677(12) .5194(3) .78573(16) .0344(5) Uani d U 1 . . C
H16 .2155 .4404 .8492 .041 Uiso calc R 1 . . H
C2' .36190(11) .2418(2) .61151(16) .0273(4) Uani d DU 1 . . C
S .4399(2) .2163(6) .5378(4) .0362(7) Uani d PDU .514(3) A 1 S
C3' .3736(11) .176(3) .7259(11) .042(3) Uani d PDU .514(3) A 1 C
H3' .3366 .1796 .7829 .050 Uiso calc PR .514(3) A 1 H
C4' .4542(8) .102(3) .7389(16) .041(3) Uani d PDU .514(3) A 1 C
H4' .4753 .0485 .8093 .049 Uiso calc PR .514(3) A 1 H
C5' .4979(11) .114(3) .6453(14) .038(3) Uani d PDU .514(3) A 1 C
H5' .5508 .0728 .6413 .045 Uiso calc PR .514(3) A 1 H
S" .3792(3) .1578(7) .7444(3) .0347(7) Uani d PDU .486(3) A 2 S
C3" .4290(8) .225(2) .5462(14) .045(4) Uani d PDU .486(3) A 2 C
H3" .4324 .2613 .4682 .054 Uiso calc PR .486(3) A 2 H
C4" .4921(10) .141(3) .6242(15) .037(3) Uani d PDU .486(3) A 2 C
H4" .5433 .1186 .5995 .044 Uiso calc PR .486(3) A 2 H
C5" .4745(8) .097(4) .7332(16) .037(2) Uani d PDU .486(3) A 2 C
H5" .5094 .0429 .7918 .044 Uiso calc PR .486(3) A 2 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'
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
C14 C1 C2 113.46(16)
C3 C2 C1 113.07(15)
C8 C3 C4 117.17(17)
C8 C3 C2 118.19(17)
C4 C3 C2 122.98(16)
C5 C4 C3 118.42(17)
C5 C4 C2' 118.13(16)
C3 C4 C2' 123.17(17)
C6 C5 C4 122.52(18)
C5 C6 C7 116.58(18)
C5 C6 C9 120.92(18)
C7 C6 C9 121.50(18)
C8 C7 C6 120.61(18)
C7 C8 C3 121.46(18)
C6 C9 C10 113.42(17)
C11 C10 C9 112.29(16)
C12 C11 C16 117.00(19)
C12 C11 C10 121.05(18)
C16 C11 C10 120.31(18)
C13 C12 C11 121.00(19)
C12 C13 C14 120.57(19)
C15 C14 C13 117.09(19)
C15 C14 C1 120.9(2)
C13 C14 C1 120.85(19)
C16 C15 C14 121.04(19)
C15 C16 C11 120.49(19)
C3' C2' C3" 114.9(12)
C3' C2' C4 121.5(7)
C3" C2' C4 123.4(7)
C3' C2' S 113.5(7)
C3" C2' S 1.9(9)
C4 C2' S 124.7(2)
C3' C2' S" 2.9(9)
C3" C2' S" 112.3(6)
C4 C2' S" 124.0(2)
S C2' S" 110.9(3)
C2' S C5' 96.1(6)
C2' C3' C4' 106.1(13)
C5' C4' C3' 117.2(15)
C4' C5' S 107.1(13)
C2' S" C5" 96.7(6)
C2' C3" C4" 106.0(12)
C5" C4" C3" 117.7(15)
C4" C5" S" 107.3(13)
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 C14 . 1.515(3) ?
C1 C2 . 1.576(3) ?
C2 C3 . 1.519(3) ?
C3 C8 . 1.392(2) ?
C3 C4 . 1.412(2) ?
C4 C5 . 1.400(2) ?
C4 C2' . 1.475(2) y
C5 C6 . 1.387(3) ?
C6 C7 . 1.392(3) ?
C6 C9 . 1.512(3) ?
C7 C8 . 1.384(3) ?
C9 C10 . 1.586(3) ?
C10 C11 . 1.512(3) ?
C11 C12 . 1.388(3) ?
C11 C16 . 1.392(3) ?
C12 C13 . 1.386(3) ?
C13 C14 . 1.390(3) ?
C14 C15 . 1.387(3) ?
C15 C16 . 1.386(3) ?
C2' C3' . 1.410(11) ?
C2' C3" . 1.425(12) ?
C2' S . 1.646(4) ?
C2' S" . 1.666(4) ?
S C5' . 1.695(12) ?
C3' C4' . 1.465(17) ?
C4' C5' . 1.371(10) ?
S" C5" . 1.688(12) ?
C3" C4" . 1.473(17) ?
C4" C5" . 1.365(10) ?
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_publ_flag
C14 C1 C2 C3 6.4(3) ?
C1 C2 C3 C8 74.8(2) ?
C1 C2 C3 C4 -90.1(2) ?
C8 C3 C4 C5 -15.3(2) ?
C2 C3 C4 C5 149.70(17) ?
C8 C3 C4 C2' 170.80(16) ?
C2 C3 C4 C2' -24.1(3) ?
C3 C4 C5 C6 1.3(3) ?
C2' C4 C5 C6 175.50(17) ?
C4 C5 C6 C7 13.3(3) ?
C4 C5 C6 C9 -155.52(18) ?
C5 C6 C7 C8 -13.8(3) ?
C9 C6 C7 C8 154.92(19) ?
C6 C7 C8 C3 -0.2(3) ?
C4 C3 C8 C7 15.0(3) ?
C2 C3 C8 C7 -150.75(18) ?
C5 C6 C9 C10 84.6(2) ?
C7 C6 C9 C10 -83.6(2) ?
C6 C9 C10 C11 2.6(3) ?
C9 C10 C11 C12 82.6(2) ?
C9 C10 C11 C16 -82.4(2) ?
C16 C11 C12 C13 13.8(3) ?
C10 C11 C12 C13 -151.71(19) ?
C11 C12 C13 C14 -0.5(3) ?
C12 C13 C14 C15 -13.1(3) ?
C12 C13 C14 C1 154.68(18) ?
C2 C1 C14 C15 75.4(2) ?
C2 C1 C14 C13 -91.9(2) ?
C13 C14 C15 C16 13.4(3) ?
C1 C14 C15 C16 -154.41(18) ?
C14 C15 C16 C11 -0.1(3) ?
C12 C11 C16 C15 -13.5(3) ?
C10 C11 C16 C15 152.10(18) ?
C5 C4 C2' C3' -31.9(10) y
C3 C4 C2' C3' 142.0(10) ?
C5 C4 C2' C3" 143.7(9) y
C3 C4 C2' C3" -42.5(10) ?
C5 C4 C2' S 142.0(3) ?
C3 C4 C2' S -44.1(3) ?
C5 C4 C2' S" -30.2(3) ?
C3 C4 C2' S" 143.7(3) ?
C3' C2' S C5' 0.8(14) ?
C3" C2' S C5' 14E1(3) ?
C4 C2' S C5' -173.5(10) ?
S" C2' S C5' -0.4(10) ?
C3" C2' C3' C4' -2(2) ?
C4 C2' C3' C4' 173.5(12) ?
S C2' C3' C4' -1.1(18) ?
S" C2' C3' C4' 23(19) ?
C2' C3' C4' C5' 1(3) ?
C3' C4' C5' S 0(3) ?
C2' S C5' C4' 0(2) ?
C3' C2' S" C5" -15E1(2) ?
C3" C2' S" C5" 1.5(13) ?
C4 C2' S" C5" 175.9(10) ?
S C2' S" C5" 2.8(10) ?
C3' C2' C3" C4" 0(2) ?
C4 C2' C3" C4" -176.1(13) ?
S C2' C3" C4" -4E1(3) ?
S" C2' C3" C4" -1.6(18) ?
C2' C3" C4" C5" 1(3) ?
C3" C4" C5" S" 0(3) ?
C2' S" C5" C4" -1(2) ?
C9 C2 C1 C10 2.10(5) y
