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#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/92/1519217.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_1519217
loop_
_publ_author_name
'Threlfall, Terry L.'
'Coles, Simon J.'
'Ward, Suzanna C.'
'Hursthouse, Michael B.'
_publ_section_title
;
 N-[4-(1,4-Dihydro-pyrazin-2-ylsulfamoyl)-phenyl]-acetamide
;
_journal_name_full               'Crystal Structure Report Archive'
_journal_page_first              167
_journal_year                    1999
_chemical_formula_sum            'C12 H12 N4 O3 S'
_chemical_formula_weight         292.32
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_cell_angle_alpha                104.81(3)
_cell_angle_beta                 103.71(3)
_cell_angle_gamma                98.48(3)
_cell_formula_units_Z            4
_cell_length_a                   8.451(2)
_cell_length_b                   11.797(2)
_cell_length_c                   14.488(3)
_cell_measurement_temperature    293(2)
_cell_volume                     1322.9(6)
_computing_cell_refinement       'DENZO & COLLECT'
_computing_data_collection
'DENZO (Otwinowski & Minor, 1997) & COLLECT (Hooft, 1998)'
_computing_data_reduction        'DENZO & COLLECT'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 9.091
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Nonius KappaCCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'Nonius FR591 rotating anode'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0551
_diffrn_reflns_av_sigmaI/netI    0.0740
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            11382
_diffrn_reflns_theta_full        25.02
_diffrn_reflns_theta_max         25.02
_diffrn_reflns_theta_min         1.83
_exptl_absorpt_coefficient_mu    0.258
_exptl_absorpt_correction_T_max  0.950
_exptl_absorpt_correction_T_min  0.950
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.468
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             608
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.284
_refine_diff_density_min         -0.327
_refine_diff_density_rms         0.050
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.970
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     457
_refine_ls_number_reflns         4612
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.970
_refine_ls_R_factor_all          0.0862
_refine_ls_R_factor_gt           0.0471
_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)+(0.0630P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1081
_refine_ls_wR_factor_ref         0.1255
_reflns_number_gt                2969
_reflns_number_total             4612
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            eCrystal-167.cif
_cod_data_source_block           99scw127a
_cod_depositor_comments
;
Citation :
Threlfall, Terry L and Coles, Simon J. and Ward, Suzanna C and 
Hursthouse, Michael B. (1999) 
University of Southampton, Crystal Structure Report Archive. 
(doi:10.5258/ecrystals/167)

More at:
http://ecrystals.chem.soton.ac.uk/167/
;
_cod_original_cell_volume        1322.9(5)
_cod_original_sg_symbol_H-M      P-1
_cod_database_code               1519217
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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 0.23896(9) 0.90913(6) 0.12174(6) 0.0468(2) Uani 1 1 d . . .
O1 O 0.1660(2) 0.79140(16) 0.12068(15) 0.0554(5) Uani 1 1 d . . .
O2 O 0.1352(2) 0.98698(18) 0.09408(16) 0.0591(6) Uani 1 1 d . . .
O3 O 0.7124(4) 1.3556(2) 0.5434(2) 0.1181(12) Uani 1 1 d . . .
N1 N 0.7243(3) 1.1608(2) 0.51793(19) 0.0510(7) Uani 1 1 d . . .
N2 N 0.3506(3) 0.8950(2) 0.04203(18) 0.0455(6) Uani 1 1 d . . .
N3 N 0.6009(3) 0.87514(18) 0.00968(17) 0.0434(6) Uani 1 1 d . . .
N4 N 0.6056(3) 0.67477(18) 0.07730(17) 0.0464(6) Uani 1 1 d . . .
C1 C 0.8893(5) 1.3102(4) 0.6749(3) 0.0670(10) Uani 1 1 d . . .
C2 C 0.7687(4) 1.2796(3) 0.5732(3) 0.0599(9) Uani 1 1 d . . .
C3 C 0.6089(4) 1.1062(2) 0.4248(2) 0.0448(7) Uani 1 1 d . . .
C4 C 0.5624(4) 0.9806(2) 0.3924(2) 0.0449(7) Uani 1 1 d . . .
C5 C 0.4488(4) 0.9198(3) 0.3009(2) 0.0465(7) Uani 1 1 d . . .
C6 C 0.3805(3) 0.9837(2) 0.2396(2) 0.0424(7) Uani 1 1 d . . .
C7 C 0.4248(4) 1.1084(3) 0.2722(3) 0.0559(9) Uani 1 1 d . . .
C8 C 0.5357(4) 1.1684(3) 0.3625(3) 0.0580(9) Uani 1 1 d . . .
C9 C 0.4792(3) 0.8323(2) 0.04375(19) 0.0371(6) Uani 1 1 d . . .
C10 C 0.7247(4) 0.8156(3) 0.0099(2) 0.0483(7) Uani 1 1 d . . .
C11 C 0.7279(4) 0.7188(2) 0.0442(2) 0.0497(7) Uani 1 1 d . . .
C12 C 0.4801(4) 0.7308(2) 0.0756(2) 0.0448(7) Uani 1 1 d . . .
S21 S 0.50845(8) 0.50786(5) -0.23770(5) 0.0427(2) Uani 1 1 d . . .
O21 O 0.5629(2) 0.62168(14) -0.25085(15) 0.0517(5) Uani 1 1 d . . .
O22 O 0.6287(2) 0.44614(15) -0.19839(15) 0.0522(5) Uani 1 1 d . . .
O23 O 0.0802(3) -0.00078(17) -0.60246(17) 0.0708(7) Uani 1 1 d . . .
N21 N 0.0506(3) 0.1808(2) -0.62031(19) 0.0498(6) Uani 1 1 d . . .
N22 N 0.3970(3) 0.5257(2) -0.15949(18) 0.0433(6) Uani 1 1 d . . .
N23 N 0.1601(3) 0.5464(2) -0.11254(18) 0.0512(6) Uani 1 1 d . . .
N24 N 0.0814(3) 0.6939(2) -0.2312(2) 0.0644(8) Uani 1 1 d . . .
C21 C -0.1122(6) 0.0029(4) -0.7497(3) 0.0682(10) Uani 1 1 d . . .
C22 C 0.0153(4) 0.0587(2) -0.6516(2) 0.0505(7) Uani 1 1 d . . .
C23 C 0.1611(3) 0.2565(2) -0.5290(2) 0.0438(7) Uani 1 1 d . . .
C24 C 0.2382(4) 0.3710(3) -0.5245(2) 0.0571(8) Uani 1 1 d . . .
C25 C 0.3434(4) 0.4482(3) -0.4358(2) 0.0550(8) Uani 1 1 d . . .
C26 C 0.3724(3) 0.4125(2) -0.3513(2) 0.0397(6) Uani 1 1 d . . .
C27 C 0.2950(4) 0.2987(2) -0.3555(2) 0.0458(7) Uani 1 1 d . . .
C28 C 0.1881(4) 0.2215(2) -0.4435(2) 0.0479(7) Uani 1 1 d . . .
C29 C 0.2569(3) 0.5751(2) -0.1676(2) 0.0419(7) Uani 1 1 d . . .
C210 C 0.0264(4) 0.5945(3) -0.1175(3) 0.0648(10) Uani 1 1 d . . .
C211 C -0.0145(5) 0.6646(3) -0.1758(3) 0.0693(10) Uani 1 1 d . . .
C212 C 0.2173(4) 0.6482(3) -0.2264(3) 0.0565(8) Uani 1 1 d . . .
H1A H 0.773(4) 1.115(3) 0.549(2) 0.064(10) Uiso 1 1 d . . .
H1B H 0.924(4) 1.243(3) 0.691(2) 0.079(11) Uiso 1 1 d . . .
H1C H 0.835(5) 1.344(3) 0.730(3) 0.124(15) Uiso 1 1 d . . .
H1D H 0.978(6) 1.377(4) 0.681(3) 0.127(16) Uiso 1 1 d . . .
H2A H 0.370(3) 0.958(2) 0.023(2) 0.054(9) Uiso 1 1 d . . .
H4 H 0.606(3) 0.936(2) 0.435(2) 0.047(7) Uiso 1 1 d . . .
H5 H 0.417(3) 0.840(2) 0.281(2) 0.048(8) Uiso 1 1 d . . .
H7 H 0.380(4) 1.148(2) 0.234(2) 0.061(9) Uiso 1 1 d . . .
H8 H 0.555(4) 1.253(3) 0.384(2) 0.069(9) Uiso 1 1 d . . .
H10 H 0.800(4) 0.850(2) -0.014(2) 0.056(9) Uiso 1 1 d . . .
H11 H 0.824(4) 0.683(2) 0.051(2) 0.062(9) Uiso 1 1 d . . .
H12 H 0.394(4) 0.698(2) 0.093(2) 0.057(9) Uiso 1 1 d . . .
H21A H 0.009(4) 0.214(3) -0.666(2) 0.063(10) Uiso 1 1 d . . .
H21B H -0.128(5) -0.072(4) -0.767(3) 0.114(17) Uiso 1 1 d . . .
H21C H -0.093(6) 0.028(4) -0.801(4) 0.135(19) Uiso 1 1 d . . .
H21D H -0.218(7) 0.019(4) -0.749(4) 0.15(2) Uiso 1 1 d . . .
H22A H 0.392(4) 0.469(3) -0.136(2) 0.068(11) Uiso 1 1 d . . .
H24 H 0.215(4) 0.391(2) -0.587(2) 0.061(9) Uiso 1 1 d . . .
H25 H 0.390(4) 0.525(3) -0.434(2) 0.074(10) Uiso 1 1 d . . .
H27 H 0.310(3) 0.275(2) -0.297(2) 0.056(8) Uiso 1 1 d . . .
H28 H 0.136(3) 0.146(2) -0.443(2) 0.064(9) Uiso 1 1 d . . .
H210 H -0.035(5) 0.571(3) -0.085(3) 0.088(14) Uiso 1 1 d . . .
H211 H -0.100(4) 0.701(3) -0.177(2) 0.078(11) Uiso 1 1 d . . .
H212 H 0.275(4) 0.669(3) -0.268(3) 0.081(12) Uiso 1 1 d . . .
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'
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
O2 S1 O1 120.22(12) . .
O2 S1 N2 103.87(12) . .
O1 S1 N2 108.08(12) . .
O2 S1 C6 109.05(13) . .
O1 S1 C6 108.54(13) . .
N2 S1 C6 106.18(13) . .
C2 N1 C3 128.7(3) . .
C9 N2 S1 124.97(19) . .
C9 N3 C10 115.9(2) . .
C12 N4 C11 116.6(2) . .
O3 C2 N1 122.4(3) . .
O3 C2 C1 121.2(3) . .
N1 C2 C1 116.3(3) . .
N1 C3 C8 124.4(2) . .
N1 C3 C4 117.5(2) . .
C8 C3 C4 118.1(3) . .
C5 C4 C3 121.0(3) . .
C4 C5 C6 119.7(3) . .
C5 C6 C7 119.4(3) . .
C5 C6 S1 120.9(2) . .
C7 C6 S1 119.7(2) . .
C8 C7 C6 121.0(3) . .
C7 C8 C3 120.8(3) . .
N3 C9 C12 121.5(2) . .
N3 C9 N2 115.0(2) . .
C12 C9 N2 123.5(3) . .
N3 C10 C11 122.4(3) . .
N4 C11 C10 121.9(3) . .
N4 C12 C9 121.6(3) . .
O21 S21 O22 119.89(12) . .
O21 S21 N22 108.51(12) . .
O22 S21 N22 103.98(12) . .
O21 S21 C26 108.25(13) . .
O22 S21 C26 109.41(12) . .
N22 S21 C26 105.92(12) . .
C22 N21 C23 126.7(3) . .
C29 N22 S21 126.7(2) . .
C210 N23 C29 115.5(3) . .
C212 N24 C211 116.1(3) . .
O23 C22 N21 123.0(3) . .
O23 C22 C21 122.4(3) . .
N21 C22 C21 114.6(3) . .
C28 C23 C24 119.6(3) . .
C28 C23 N21 121.6(3) . .
C24 C23 N21 118.8(3) . .
C25 C24 C23 120.1(3) . .
C26 C25 C24 120.2(3) . .
C25 C26 C27 119.8(3) . .
C25 C26 S21 121.3(2) . .
C27 C26 S21 118.9(2) . .
C28 C27 C26 120.4(3) . .
C27 C28 C23 119.8(3) . .
N23 C29 C212 121.4(3) . .
N23 C29 N22 114.2(3) . .
C212 C29 N22 124.4(3) . .
N23 C210 C211 123.5(4) . .
N24 C211 C210 121.5(3) . .
N24 C212 C29 122.0(3) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
S1 O2 1.4257(19) .
S1 O1 1.4287(18) .
S1 N2 1.648(2) .
S1 C6 1.753(3) .
O3 C2 1.201(4) .
N1 C2 1.370(4) .
N1 C3 1.390(4) .
N2 C9 1.401(3) .
N3 C9 1.331(3) .
N3 C10 1.344(3) .
N4 C12 1.328(3) .
N4 C11 1.332(4) .
C1 C2 1.500(5) .
C3 C8 1.394(4) .
C3 C4 1.398(4) .
C4 C5 1.379(4) .
C5 C6 1.384(4) .
C6 C7 1.388(4) .
C7 C8 1.356(4) .
C9 C12 1.390(3) .
C10 C11 1.358(4) .
S21 O21 1.4286(17) .
S21 O22 1.4292(19) .
S21 N22 1.630(2) .
S21 C26 1.753(3) .
O23 C22 1.218(3) .
N21 C22 1.358(3) .
N21 C23 1.408(4) .
N22 C29 1.389(3) .
N23 C210 1.332(4) .
N23 C29 1.336(3) .
N24 C212 1.333(4) .
N24 C211 1.338(4) .
C21 C22 1.484(5) .
C23 C28 1.384(4) .
C23 C24 1.387(4) .
C24 C25 1.376(4) .
C25 C26 1.373(4) .
C26 C27 1.384(3) .
C27 C28 1.374(4) .
C29 C212 1.382(4) .
C210 C211 1.349(5) .
