#------------------------------------------------------------------------------
#$Date: 2016-02-19 16:29:56 +0200 (Fri, 19 Feb 2016) $
#$Revision: 176759 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/85/2008573.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_2008573
loop_
_publ_author_name
'Zukerman-Schpector, J.'
'Gruber, Jonas'
'Camilo, Fernanda Ferraz'
_publ_section_title
;
 Two new 2,3-substituted 5-norbornenes
;
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              980
_journal_page_last               983
_journal_paper_doi               10.1107/S010827019900236X
_journal_volume                  55
_journal_year                    1999
_chemical_formula_moiety         'C15 H15 N O3 S'
_chemical_formula_sum            'C15 H15 N O3 S'
_chemical_formula_weight         289.34
_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'
_cell_angle_alpha                90.00
_cell_angle_beta                 107.292(8)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.7630(10)
_cell_length_b                   12.097(2)
_cell_length_c                   12.1640(10)
_cell_measurement_reflns_used    20
_cell_measurement_temperature    293
_cell_measurement_theta_max      13.53
_cell_measurement_theta_min      8.12
_cell_volume                     1371.7(3)
_computing_cell_refinement       'CAD-4 Software'
_computing_data_collection       'CAD-4 Software (Enraf-Nonius,1989)'
_computing_data_reduction        'MolEN (Fair, 1990)'
_computing_molecular_graphics    'ZORTEP (Zsolnai, 1995)'
_computing_publication_material  'SHELXL97 and PARST95 (Nardelli, 1995)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS86 (Sheldrick, 1990)'
_diffrn_measurement_device_type  'Enraf-Nonius CAD-4'
_diffrn_measurement_method       ω/2θ
_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  0.039
_diffrn_reflns_limit_h_max       0
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            2698
_diffrn_reflns_theta_max         25.46
_diffrn_standards_decay_%        1.1
_diffrn_standards_interval_time  30
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.242
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.401
_exptl_crystal_density_meas      ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             608.0
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.225
_refine_diff_density_min         -0.276
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2541
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.150
_refine_ls_R_factor_gt           0.050
_refine_ls_shift/su_max          <0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0834P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.165
_reflns_number_gt                1369
_reflns_number_total             2541
_reflns_threshold_expression     F²>2\sF²
_cod_data_source_file            gs1033.cif
_cod_data_source_block           2b
_cod_depositor_comments
;
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 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc w =
1/[\s^2^(Fo^2^)+(0.0834P)^2^] where P=(Fo^2^+2Fc^2^)/3' 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^(Fo^2^)+(0.0834P)^2^]
where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2008573
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
S .70472(11) .04920(10) .25782(9) .0584(4) Uani d . 1 . . S
N .0333(3) -.1907(3) -.0358(3) .0459(8) Uani d . 1 . . N
O1 -.0475(3) -.2577(3) -.0133(2) .0657(9) Uani d . 1 . . O
O2 .0423(3) -.1765(3) -.1328(2) .0736(10) Uani d . 1 . . O
O3 .7201(3) .1248(3) .4602(2) .0765(10) Uani d . 1 . . O
C1 .4584(4) .2641(3) .3723(3) .0451(10) Uani d . 1 . . C
H1 .5004 .3316 .3516 .054 Uiso calc R 1 . . H
C2 .4929(3) .1545(3) .3172(3) .0372(9) Uani d . 1 . . C
H2 .4716 .1662 .2341 .045 Uiso calc R 1 . . H
C3 .3819(3) .0714(3) .3375(3) .0350(8) Uani d . 1 . . C
H3 .4332 .0187 .3966 .042 Uiso calc R 1 . . H
C4 .2888(4) .1490(3) .3922(3) .0444(10) Uani d . 1 . . C
H4 .1925 .1221 .3874 .053 Uiso calc R 1 . . H
C5 .3833(4) .1772(3) .5108(3) .0491(10) Uani d . 1 . . C
H5 .3728 .1517 .5800 .059 Uiso calc R 1 . . H
C6 .4844(4) .2450(3) .4989(3) .0514(11) Uani d . 1 . . C
H6 .5581 .2753 .5582 .062 Uiso calc R 1 . . H
C7 .2955(4) .2568(3) .3296(4) .0528(11) Uani d . 1 . . C
H7A .2488 .3176 .3562 .063 Uiso calc R 1 . . H
H7B .2585 .2498 .2466 .063 Uiso calc R 1 . . H
C8 .6454(4) .1147(3) .3633(3) .0387(9) Uani d . 1 . . C
C9 .8833(4) .0089(4) .3380(3) .0564(11) Uani d . 1 . . C
H9A .9268 .0665 .3913 .085 Uiso calc R 1 . . H
H9B .9391 -.0033 .2861 .085 Uiso calc R 1 . . H
H9C .8798 -.0579 .3796 .085 Uiso calc R 1 . . H
C10 .2929(3) .0062(3) .2346(3) .0335(8) Uani d . 1 . . C
C11 .2807(4) .0292(3) .1206(3) .0437(9) Uani d . 1 . . C
H11 .3299 .0893 .1033 .052 Uiso calc R 1 . . H
C12 .1968(4) -.0351(3) .0319(3) .0443(9) Uani d . 1 . . C
H12 .1902 -.0189 -.0443 .053 Uiso calc R 1 . . H
C13 .1238(4) -.1230(3) .0583(3) .0365(8) Uani d . 1 . . C
C14 .1331(4) -.1482(3) .1693(3) .0441(9) Uani d . 1 . . C
H14 .0824 -.2078 .1857 .053 Uiso calc R 1 . . H
C15 .2181(4) -.0846(3) .2571(3) .0427(9) Uani d . 1 . . C
H15 .2257 -.1027 .3330 .051 Uiso calc R 1 . . H
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
S .0504(6) .0794(8) .0421(6) .0164(6) .0086(5) -.0124(5)
N .0441(19) .048(2) .0426(19) .0003(16) .0080(15) -.0095(16)
O1 .068(2) .0606(19) .0635(19) -.0274(17) .0120(16) -.0049(15)
O2 .081(2) .100(3) .0392(17) -.0264(19) .0160(15) -.0192(17)
O3 .0486(17) .140(3) .0360(15) .0156(18) .0054(13) -.0163(18)
C1 .045(2) .031(2) .057(3) -.0013(17) .0132(18) -.0023(18)
C2 .041(2) .042(2) .0285(18) -.0010(17) .0097(15) -.0007(15)
C3 .0359(19) .037(2) .0324(19) .0052(16) .0112(15) .0016(15)
C4 .041(2) .048(2) .049(2) .0011(18) .0214(18) -.0072(18)
C5 .054(3) .051(3) .046(2) .010(2) .020(2) -.0144(19)
C6 .057(3) .046(2) .047(2) .008(2) .0094(19) -.0169(19)
C7 .046(2) .046(2) .061(3) .017(2) .0086(19) -.001(2)
C8 .0305(18) .047(2) .038(2) -.0005(17) .0099(16) -.0002(17)
C9 .035(2) .069(3) .060(3) .013(2) .0072(19) .001(2)
C10 .0335(18) .0329(19) .0333(19) .0024(16) .0088(15) .0004(16)
C11 .050(2) .042(2) .040(2) -.0128(18) .0138(17) .0015(17)
C12 .050(2) .054(2) .0279(18) -.002(2) .0107(16) .0036(18)
C13 .038(2) .034(2) .036(2) .0023(17) .0091(16) -.0025(16)
C14 .052(2) .039(2) .043(2) -.0048(18) .0163(18) .0018(17)
C15 .052(2) .045(2) .0289(19) -.0027(19) .0089(17) .0007(17)
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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 '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'
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_publ_flag
C8 S C9 101.83(18) yes
O1 N O2 123.3(3) yes
O1 N C13 118.4(3) yes
O2 N C13 118.4(3) yes
C6 C1 C7 100.5(3) no
C6 C1 C2 108.4(3) no
C7 C1 C2 98.1(3) no
C8 C2 C3 113.2(3) no
C8 C2 C1 115.2(3) no
C3 C2 C1 103.3(3) no
C10 C3 C2 117.5(3) no
C10 C3 C4 113.3(3) no
C2 C3 C4 101.4(3) no
C5 C4 C7 100.4(3) no
C5 C4 C3 105.8(3) no
C7 C4 C3 100.5(3) no
C6 C5 C4 107.5(4) no
C5 C6 C1 107.7(3) no
C4 C7 C1 94.3(3) yes
O3 C8 C2 125.6(3) yes
O3 C8 S 122.2(3) yes
C2 C8 S 112.3(2) yes
C11 C10 C15 117.5(3) no
C11 C10 C3 125.5(3) no
C15 C10 C3 117.0(3) no
C12 C11 C10 121.6(3) no
C13 C12 C11 118.8(3) no
C14 C13 C12 121.4(3) no
C14 C13 N 119.7(3) no
C12 C13 N 118.9(3) no
C13 C14 C15 119.5(3) no
C14 C15 C10 121.3(3) no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
S C8 1.747(4) yes
S C9 1.794(4) yes
N O1 1.218(4) yes
N O2 1.221(4) yes
N C13 1.470(4) yes
O3 C8 1.194(4) yes
C1 C6 1.502(5) no
C1 C7 1.522(5) no
C1 C2 1.566(5) no
C2 C8 1.505(5) no
C2 C3 1.551(5) no
C3 C10 1.515(4) no
C3 C4 1.584(5) no
C4 C5 1.503(5) no
C4 C7 1.521(5) no
C5 C6 1.323(5) yes
C10 C11 1.384(5) no
C10 C15 1.390(5) no
C11 C12 1.384(5) no
C12 C13 1.371(5) no
C13 C14 1.360(5) no
C14 C15 1.377(5) 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_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
C15 H15 O3 3_656 0.93 2.43 3.345(5) 170 yes
C9 H9C O1 2_545 0.96 2.57 3.498(5) 162 yes
