#------------------------------------------------------------------------------
#$Date: 2017-10-14 21:27:35 +0200 (Sat 14 de Oct de 2017) $
#$Revision: 202017 $
#$URL: svn://www.crystallography.net/cod/cif/7/15/00/7150078.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_7150078
loop_
_publ_author_name
'Fifer, Nathan L.'
'White, Jonathan M.'
_publ_section_title
;
 Determining the sigma-donor ability of the cyclopropane C-C bond.
;
_journal_issue                   9
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              1776
_journal_page_last               1780
_journal_paper_doi               10.1039/b503124a
_journal_volume                  3
_journal_year                    2005
_chemical_formula_sum            'C10 H10 N2 O5 S'
_chemical_formula_weight         270.26
_chemical_name_systematic
;
?
;
_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'
_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                 94.289(5)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   5.1517(14)
_cell_length_b                   11.726(3)
_cell_length_c                   18.705(5)
_cell_measurement_reflns_used    1017
_cell_measurement_temperature    130(2)
_cell_measurement_theta_max      23.93
_cell_measurement_theta_min      2.18
_cell_volume                     1126.8(5)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_diffrn_ambient_temperature      130(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0887
_diffrn_reflns_av_sigmaI/netI    0.0753
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            5769
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.05
_exptl_absorpt_coefficient_mu    0.303
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.593
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.267
_refine_diff_density_min         -0.360
_refine_diff_density_rms         0.065
_refine_ls_extinction_coef       0.0003(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         1981
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.023
_refine_ls_R_factor_all          0.0746
_refine_ls_R_factor_gt           0.0545
_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)+(0.0352P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1061
_refine_ls_wR_factor_ref         0.1137
_reflns_number_gt                1502
_reflns_number_total             1981
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b503124a.txt
_cod_data_source_block           jmwnf16
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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 
;
_cod_original_sg_symbol_H-M      'P2(1)/c '
_cod_database_code               7150078
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_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
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.78435(16) 0.99794(6) 0.91125(4) 0.0284(3) Uani 1 1 d . . .
O2 O 0.9972(4) 0.82104(18) 0.96103(12) 0.0361(6) Uani 1 1 d . . .
O3 O 0.9605(4) 0.64316(18) 0.93008(11) 0.0341(6) Uani 1 1 d . . .
N1 N 0.8865(5) 0.7422(2) 0.92679(13) 0.0262(6) Uani 1 1 d . . .
O5 O 0.2122(4) 0.52363(17) 0.78018(11) 0.0345(6) Uani 1 1 d . . .
O4 O -0.0674(4) 0.64904(18) 0.73891(12) 0.0364(6) Uani 1 1 d . . .
N2 N 0.1365(5) 0.6223(2) 0.77158(13) 0.0266(7) Uani 1 1 d . . .
C8 C 0.3020(6) 0.7132(2) 0.80400(15) 0.0219(7) Uani 1 1 d . . .
C7 C 0.5146(6) 0.6856(2) 0.84803(14) 0.0206(7) Uani 1 1 d . . .
H10 H 0.5609 0.6098 0.8560 0.025 Uiso 1 1 calc R . .
O1 O 0.6478(4) 1.11009(16) 0.87189(11) 0.0295(6) Uani 1 1 d . . .
C5 C 0.5963(6) 0.8890(2) 0.87007(16) 0.0233(7) Uani 1 1 d . . .
C10 C 0.3792(6) 0.9127(2) 0.82351(15) 0.0235(7) Uani 1 1 d . . .
H6 H 0.3336 0.9883 0.8141 0.028 Uiso 1 1 calc R . .
C9 C 0.2309(6) 0.8274(2) 0.79116(15) 0.0242(7) Uani 1 1 d . . .
H5 H 0.0846 0.8450 0.7610 0.029 Uiso 1 1 calc R . .
C6 C 0.6610(6) 0.7727(2) 0.88073(15) 0.0206(7) Uani 1 1 d . . .
C1 C 0.4759(6) 1.1752(2) 0.91568(17) 0.0295(8) Uani 1 1 d . . .
H1A H 0.5507 1.1800 0.9647 0.035 Uiso 1 1 calc R . .
H1B H 0.3076 1.1381 0.9157 0.035 Uiso 1 1 calc R . .
C2 C 0.4465(6) 1.2907(3) 0.88417(17) 0.0300(8) Uani 1 1 d . . .
H2A H 0.3369 1.2959 0.8392 0.036 Uiso 1 1 calc R . .
C4 C 0.6675(7) 1.3717(3) 0.89204(17) 0.0337(9) Uani 1 1 d . . .
H4A H 0.6930 1.4225 0.8522 0.040 Uiso 1 1 calc R . .
H4B H 0.8265 1.3461 0.9182 0.040 Uiso 1 1 calc R . .
C3 C 0.4367(7) 1.3914(3) 0.93340(18) 0.0346(9) Uani 1 1 d . . .
H3A H 0.3213 1.4538 0.9186 0.042 Uiso 1 1 calc R . .
H3B H 0.4549 1.3773 0.9846 0.042 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'
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'
O O 0.0106 0.0060 '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
_geom_angle_publ_flag
O1 S1 C5 100.55(13) . . ?
O3 N1 O2 123.6(3) . . ?
O3 N1 C6 120.1(3) . . ?
O2 N1 C6 116.4(2) . . ?
O4 N2 O5 124.2(3) . . ?
O4 N2 C8 118.3(3) . . ?
O5 N2 C8 117.5(3) . . ?
C7 C8 C9 121.2(3) . . ?
C7 C8 N2 119.6(3) . . ?
C9 C8 N2 119.1(3) . . ?
C8 C7 C6 118.7(3) . . ?
C8 C7 H10 120.7 . . ?
C6 C7 H10 120.7 . . ?
C1 O1 S1 115.08(18) . . ?
C10 C5 C6 116.8(3) . . ?
C10 C5 S1 121.5(2) . . ?
C6 C5 S1 121.7(2) . . ?
C9 C10 C5 121.6(3) . . ?
C9 C10 H6 119.2 . . ?
C5 C10 H6 119.2 . . ?
C10 C9 C8 119.4(3) . . ?
C10 C9 H5 120.3 . . ?
C8 C9 H5 120.3 . . ?
C7 C6 C5 122.3(3) . . ?
C7 C6 N1 118.0(3) . . ?
C5 C6 N1 119.7(3) . . ?
O1 C1 C2 107.6(2) . . ?
O1 C1 H1A 110.2 . . ?
C2 C1 H1A 110.2 . . ?
O1 C1 H1B 110.2 . . ?
C2 C1 H1B 110.2 . . ?
H1A C1 H1B 108.5 . . ?
C1 C2 C4 119.5(3) . . ?
C1 C2 C3 118.9(3) . . ?
C4 C2 C3 59.7(2) . . ?
C1 C2 H2A 115.7 . . ?
C4 C2 H2A 115.7 . . ?
C3 C2 H2A 115.7 . . ?
C2 C4 C3 60.8(2) . . ?
C2 C4 H4A 117.7 . . ?
C3 C4 H4A 117.7 . . ?
C2 C4 H4B 117.7 . . ?
C3 C4 H4B 117.7 . . ?
H4A C4 H4B 114.8 . . ?
C4 C3 C2 59.5(2) . . ?
C4 C3 H3A 117.8 . . ?
C2 C3 H3A 117.8 . . ?
C4 C3 H3B 117.8 . . ?
C2 C3 H3B 117.8 . . ?
H3A C3 H3B 115.0 . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O1 1.640(2) . ?
S1 C5 1.747(3) . ?
O2 N1 1.239(3) . ?
O3 N1 1.223(3) . ?
N1 C6 1.439(4) . ?
O5 N2 1.227(3) . ?
O4 N2 1.216(3) . ?
N2 C8 1.467(4) . ?
C8 C7 1.359(4) . ?
C8 C9 1.404(4) . ?
C7 C6 1.385(4) . ?
C7 H10 0.9300 . ?
O1 C1 1.465(3) . ?
C5 C10 1.393(4) . ?
C5 C6 1.415(4) . ?
C10 C9 1.372(4) . ?
C10 H6 0.9300 . ?
C9 H5 0.9300 . ?
C1 C2 1.480(4) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C4 1.482(4) . ?
C2 C3 1.501(4) . ?
C2 H2A 0.9800 . ?
C4 C3 1.484(4) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C3 H3A 0.9700 . ?
C3 H3B 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_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O4 N2 C8 C7 172.0(3) . . . . ?
O5 N2 C8 C7 -7.0(4) . . . . ?
O4 N2 C8 C9 -5.4(4) . . . . ?
O5 N2 C8 C9 175.6(3) . . . . ?
C9 C8 C7 C6 0.4(4) . . . . ?
N2 C8 C7 C6 -177.0(2) . . . . ?
C5 S1 O1 C1 103.7(2) . . . . ?
O1 S1 C5 C10 -5.8(3) . . . . ?
O1 S1 C5 C6 172.4(2) . . . . ?
C6 C5 C10 C9 1.8(4) . . . . ?
S1 C5 C10 C9 -179.9(2) . . . . ?
C5 C10 C9 C8 -1.3(4) . . . . ?
C7 C8 C9 C10 0.2(4) . . . . ?
N2 C8 C9 C10 177.5(3) . . . . ?
C8 C7 C6 C5 0.2(4) . . . . ?
C8 C7 C6 N1 -179.6(2) . . . . ?
C10 C5 C6 C7 -1.3(4) . . . . ?
S1 C5 C6 C7 -179.6(2) . . . . ?
C10 C5 C6 N1 178.5(2) . . . . ?
S1 C5 C6 N1 0.3(4) . . . . ?
O3 N1 C6 C7 8.0(4) . . . . ?
O2 N1 C6 C7 -172.7(3) . . . . ?
O3 N1 C6 C5 -171.9(3) . . . . ?
O2 N1 C6 C5 7.5(4) . . . . ?
S1 O1 C1 C2 160.2(2) . . . . ?
O1 C1 C2 C4 -72.4(3) . . . . ?
O1 C1 C2 C3 -141.9(3) . . . . ?
C1 C2 C4 C3 -108.2(3) . . . . ?
C1 C2 C3 C4 109.2(3) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9406071
