#------------------------------------------------------------------------------
#$Date: 2016-02-19 16:29:56 +0200 (Fri, 19 Feb 2016) $
#$Revision: 176759 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/42/2004250.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_2004250
loop_
_publ_author_name
'Jones, R.'
'Rattray, A. G. M.'
'Scheffer, J. R.'
'Trotter, J.'
_publ_section_title
;Dimethyl
 4b,8b,8c,8d-Tetrahydrodibenzo[a,f]cyclopropa[cd]pentalene-8b-carboxylate-8c-thionocarboxylate
 and the Corresponding 8c-Thiolocarboxylate
;
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              2691
_journal_page_last               2694
_journal_paper_doi               10.1107/S0108270195009012
_journal_volume                  51
_journal_year                    1995
_chemical_formula_moiety         'C20 H16 O3 S'
_chemical_formula_sum            'C20 H16 O3 S'
_chemical_formula_weight         336.40
_chemical_name_systematic
;
Dimethyl 4b,8b,8c,8d-tetrahydrodibenzo[a,f]
cyclopropa[cd]pentalene-8b-carboxylate-8c-
thiolocarboxylate
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_type_scat_source           IntTabIV
_cell_angle_alpha                90
_cell_angle_beta                 90.900(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   7.9110(10)
_cell_length_b                   14.4570(10)
_cell_length_c                   14.8130(10)
_cell_measurement_reflns_used    20
_cell_measurement_temperature    294
_cell_measurement_theta_max      57.3
_cell_measurement_theta_min      54.0
_cell_volume                     1693.9(3)
_computing_cell_refinement       'MSC/AFC Diffractometer Control Software'
_computing_data_collection
;
MSC/AFC Diffractometer Control Software
(Molecular Structure Corporation, 1988)
;
_computing_data_reduction
'TEXSAN (Molecular Structure Corporation, 1990)'
_computing_publication_material  TEXSAN
_computing_structure_refinement  TEXSAN
_computing_structure_solution    TEXSAN
_diffrn_ambient_temperature      294
_diffrn_measurement_device       'Rigaku AFC-6S'
_diffrn_measurement_method       ω-2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'X-ray tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.018
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            3837
_diffrn_reflns_theta_max         77.4
_diffrn_standards_decay_%        0.05
_diffrn_standards_interval_count 200
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    1.8
_exptl_absorpt_correction_T_max  1.00
_exptl_absorpt_correction_T_min  0.92
_exptl_absorpt_correction_type   '\y scan (North, Phillips & Mathews, 1968)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.319
_exptl_crystal_description       plate
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.25
_refine_diff_density_min         -0.39
_refine_ls_extinction_coef       '0.53 \\times 10^-5^'
_refine_ls_extinction_method
'Zachariasen (1967) Type II, Gaussian isotropic'
_refine_ls_goodness_of_fit_obs   2.8
_refine_ls_hydrogen_treatment    'H atoms refined isotropically'
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     282
_refine_ls_number_reflns         2880
_refine_ls_number_restraints     0
_refine_ls_R_factor_obs          0.042
_refine_ls_shift/esd_max         0.12
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     'w = 1/σ²(F)'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_obs         0.064
_reflns_number_observed          2880
_reflns_number_total             3592
_reflns_observed_criterion       I>3\s(I)
_cod_data_source_file            fg1099.cif
_cod_data_source_block           thiolo
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'w = 1/\s^2^(F)' was changed to
'calc'. New tag '_refine_ls_weighting_details' was created. The value
of the new tag was set to 'w = 1/\s^2^(F)'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2004250
loop_
_symmetry_equiv_pos_as_xyz
'   +x,   +y,   +z'
'   -x,   -y,   -z'
1/2+x,1/2-y,1/2+z
1/2-x,1/2+y,1/2-z
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
S .64182(8) .18083(4) .85445(4) .0600(4)
O1 .8484(2) .04860(10) .80580(10) .0520(10)
O2 .7124(2) .01660(10) .57080(10) .0640(10)
O3 .9789(3) -.01610(10) .61030(10) .0790(10)
C1 1.0246(3) .4209(2) .71360(10) .0510(10)
C2 1.1946(4) .4453(2) .7099(2) .0670(10)
C3 1.3158(3) .3814(2) .6896(2) .0680(10)
C4 1.2735(3) .2903(2) .6717(2) .0570(10)
C4a 1.1054(2) .26380(10) .67730(10) .0410(10)
C5 .7783(3) .19910(10) .46010(10) .0460(10)
C6 .6985(3) .2710(2) .41390(10) .0520(10)
C7 .6490(3) .3505(2) .45870(10) .0490(10)
C8 .6775(2) .35990(10) .55050(10) .0400(10)
C8a .7522(2) .28760(10) .59740(10) .0330(10)
C9 .8090(2) .28410(10) .69560(10) .0320(10)
C9a .9821(2) .32940(10) .69780(10) .0370(10)
C10 1.0311(2) .16950(10) .67710(10) .0390(10)
C10a .8030(2) .20770(10) .55210(10) .0360(10)
C11 .8521(2) .18040(10) .71130(10) .0330(10)
C12 .8817(2) .14070(10) .61660(10) .0360(10)
C13 .7932(2) .12480(10) .78880(10) .0360(10)
C14 .6206(5) .1016(2) .9464(2) .0630(10)
C15 .8659(3) .03810(10) .59980(10) .0460(10)
C16 .6836(6) -.0797(2) .5466(3) .087(2)
H1 .936(3) .465(2) .730(2) .060(10)
H2 1.224(5) .507(3) .730(2) .100(10)
H3 1.432(5) .399(2) .687(2) .100(10)
H4 1.358(3) .244(2) .657(2) .060(10)
H5 .810(3) .147(2) .429(2) .060(10)
H6 .687(3) .262(2) .351(2) .070(10)
H7 .593(3) .399(2) .423(2) .060(10)
H8 .647(3) .419(2) .583(2) .050(10)
H9 .723(3) .3100(10) .7370(10) .030(10)
H10 1.099(3) .119(2) .6990(10) .040(10)
H14a .535(4) .128(2) .986(2) .090(10)
H14b .593(6) .048(3) .925(3) .130(10)
H14c .728(6) .090(3) .971(3) .130(10)
H16a .755(7) -.097(4) .494(4) .16(2)
H16b .708(6) -0.114(3) .591(4) .140(10)
H16c .574(7) -.087(3) .528(3) .15(2)
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C13 S C14 101.50(10) no
C15 O2 C16 116.5(2) no
C2 C1 C9a 117.9(2) no
C1 C2 C3 121.2(3) no
C2 C3 C4 121.1(3) no
C3 C4 C4a 118.7(2) no
C4 C4a C9a 119.9(2) no
C4 C4a C10 129.3(2) no
C9a C4a C10 110.2(2) no
C6 C5 C10a 118.4(2) no
C5 C6 C7 120.9(2) no
C6 C7 C8 120.6(2) no
C7 C8 C8a 118.8(2) no
C8 C8a C9 128.7(2) no
C8 C8a C10a 120.5(2) no
C9 C8a C10a 110.50(10) no
C8a C9 C9a 105.10(10) no
C8a C9 C11 103.70(10) no
C9a C9 C11 102.60(10) no
C1 C9a C4a 121.1(2) no
C1 C9a C9 129.3(2) no
C4a C9a C9 109.6(2) no
C4a C10 C11 106.0(2) no
C4a C10 C12 123.6(2) no
C11 C10 C12 60.50(10) no
C5 C10a C8a 120.8(2) no
C5 C10a C12 128.8(2) no
C8a C10a C12 110.50(10) no
C9 C11 C10 104.70(10) no
C9 C11 C12 105.10(10) no
C9 C11 C13 124.60(10) no
C10 C11 C12 60.10(10) no
C10 C11 C13 120.50(10) no
C12 C11 C13 124.00(10) no
C10 C12 C10a 120.7(2) no
C10 C12 C11 59.40(10) no
C10 C12 C15 115.2(2) no
C10a C12 C11 105.90(10) no
C10a C12 C15 120.0(2) no
C11 C12 C15 120.3(2) no
S C13 O1 123.60(10) no
S C13 C11 113.90(10) no
O1 C13 C11 122.5(2) no
O2 C15 O3 124.8(2) no
O2 C15 C12 111.0(2) no
O3 C15 C12 124.2(2) no
C2 C1 H1 123(2) no
C9a C1 H1 119(2) no
C1 C2 H2 117(2) no
C3 C2 H2 122(2) no
C2 C3 H3 121(2) no
C4 C3 H3 118(2) no
C3 C4 H4 122(2) no
C4a C4 H4 119(2) no
C6 C5 H5 119(2) no
C10a C5 H5 122(2) no
C5 C6 H6 115(2) no
C7 C6 H6 124(2) no
C6 C7 H7 118(2) no
C8 C7 H7 122(2) no
C7 C8 H8 121(2) no
C8a C8 H8 120(2) no
C8a C9 H9 113(2) no
C9a C9 H9 117(2) no
C11 C9 H9 115(2) no
C4a C10 H10 119(2) no
C11 C10 H10 119(2) no
C12 C10 H10 114(2) no
S C14 H14a 106(2) no
S C14 H14b 109(2) no
S C14 H14c 108(2) no
H14a C14 H14b 113(3) no
H14a C14 H14c 118(3) no
H14b C14 H14c 102(3) no
O2 C16 H16a 110(2) no
O2 C16 H16b 110(2) no
O2 C16 H16c 109(2) no
H16a C16 H16b 110(3) no
H16a C16 H16c 106(3) no
H16b C16 H16c 112(3) no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
S C13 1.753(2) no
S C14 1.790(3) no
O1 C13 1.210(2) no
O2 C15 1.319(3) no
O2 C16 1.455(4) no
O3 C15 1.197(3) no
C1 C2 1.392(4) no
C1 C9a 1.384(3) no
C2 C3 1.368(4) no
C3 C4 1.383(4) no
C4 C4a 1.388(3) no
C4a C9a 1.397(3) no
C4a C10 1.485(3) no
C5 C6 1.391(3) no
C5 C10a 1.379(3) no
C6 C7 1.387(3) no
C7 C8 1.382(3) no
C8 C8a 1.383(3) no
C8a C9 1.517(2) no
C8a C10a 1.398(3) no
C9 C9a 1.518(3) no
C9 C11 1.554(2) no
C10 C11 1.520(3) no
C10 C12 1.530(3) no
C10a C12 1.490(3) no
C11 C12 1.537(3) no
C11 C13 1.483(3) no
C12 C15 1.509(3) no
C1 H1 0.98(3) no
C2 H2 0.97(4) no
C3 H3 0.96(3) no
C4 H4 0.97(3) no
C5 H5 0.92(3) no
C6 H6 0.94(3) no
C7 H7 0.98(3) no
C8 H8 1.01(3) no
C9 H9 1.00(2) no
C10 H10 0.96(2) no
C14 H14a 0.98(3) no
C14 H14b 0.86(4) no
C14 H14c 0.93(4) no
C16 H16a 1.00(6) no
C16 H16b 0.84(5) no
C16 H16c 0.91(5) no
