#------------------------------------------------------------------------------
#$Date: 2016-02-18 16:37:37 +0100 (jue 18 de feb de 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/83/1508378.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_1508378
loop_
_publ_author_name
'Laus, Gerhard'
'Adamer, Verena'
'Hummel, Michael'
'Kahlenberg, Volker'
'Wurst, Klaus'
'Nerdinger, Sven'
'Schottenberger, Herwig'
_publ_section_title
;
 Crystal Structure of 2-Ethylimidazole-1-sulfonyl Azide: A New Azidation
 Reagent
;
_journal_issue                   1
_journal_name_full               Crystals
_journal_page_first              118
_journal_page_last               126
_journal_paper_doi               10.3390/cryst2010118
_journal_volume                  2
_journal_year                    2012
_chemical_formula_moiety         'C5 H7 N5 O2 S'
_chemical_formula_sum            'C5 H7 N5 O2 S'
_chemical_formula_weight         201.22
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_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_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_creation_date             2008-05-07T14:37:33-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_cell_angle_alpha                90
_cell_angle_beta                 100.383(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   8.0815(7)
_cell_length_b                   10.0732(9)
_cell_length_c                   10.7291(10)
_cell_measurement_reflns_used    3583
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.70
_cell_measurement_theta_min      1.93
_cell_volume                     859.12(13)
_computing_cell_refinement       'STOE X-AREA'
_computing_data_collection       'STOE X-AREA'
_computing_data_reduction        'STOE X-RED'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR2002 (Burla et al., 2003)'
_diffrn_ambient_temperature      173(2)
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       '2-circle goniometer'
_diffrn_measurement_device_type  'STOE IPDS 2'
_diffrn_measurement_method       'rotation method'
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0502
_diffrn_reflns_av_unetI/netI     0.0429
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            4991
_diffrn_reflns_theta_full        25.27
_diffrn_reflns_theta_max         25.70
_diffrn_reflns_theta_min         1.93
_diffrn_source
'sealed X-ray tube, 12 x 0.4 mm long-fine focus'
_exptl_absorpt_coefficient_mu    0.35
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.556
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       'irregular fragment'
_exptl_crystal_F_000             416
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.22
_refine_diff_density_max         0.273
_refine_diff_density_min         -0.316
_refine_diff_density_rms         0.05
_refine_ls_extinction_coef       0.010(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     120
_refine_ls_number_reflns         1562
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.005
_refine_ls_R_factor_all          0.0536
_refine_ls_R_factor_gt           0.0377
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0550P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0893
_refine_ls_wR_factor_ref         0.0943
_reflns_number_gt                1211
_reflns_number_total             1562
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file
C5H7N5O2S_P21_c_crystals-02-00118-s002_DC122.cif
_cod_data_source_block           VA25_chateigner_1508378
_cod_original_cell_volume        859.11(13)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1508378
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
-x,1/2+y,1/2-z
-x,-y,-z
x,1/2-y,1/2+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
S1 S 0.36300(7) 0.09145(6) 0.72614(5) 0.0312(2) Uani 1 1 d .
O1 O 0.50113(19) 0.00370(18) 0.74128(18) 0.0446(5) Uani 1 1 d .
O2 O 0.3378(2) 0.18180(17) 0.82242(15) 0.0381(4) Uani 1 1 d .
N1 N 0.1883(2) 0.00266(18) 0.69374(17) 0.0283(4) Uani 1 1 d .
N3 N 0.3734(2) 0.1712(2) 0.59269(18) 0.0363(5) Uani 1 1 d .
N2 N -0.0007(2) -0.14333(19) 0.60350(18) 0.0323(5) Uani 1 1 d .
N4 N 0.2842(3) 0.2761(2) 0.57996(18) 0.0342(5) Uani 1 1 d .
N5 N 0.2125(3) 0.3700(2) 0.5589(2) 0.0444(6) Uani 1 1 d .
C1 C 0.1561(3) -0.1084(2) 0.6135(2) 0.0285(5) Uani 1 1 d .
C3 C -0.0742(3) -0.0540(2) 0.6759(2) 0.0326(5) Uani 1 1 d .
H3 H -0.189 -0.0567 0.6848 0.039 Uiso 1 1 calc R
C2 C 0.0366(3) 0.0362(2) 0.7316(2) 0.0311(5) Uani 1 1 d .
H2 H 0.0167 0.1074 0.7851 0.037 Uiso 1 1 calc R
C4 C 0.2869(3) -0.1715(3) 0.5522(2) 0.0374(6) Uani 1 1 d .
H4A H 0.3823 -0.1991 0.6185 0.045 Uiso 1 1 calc R
H4B H 0.3295 -0.1055 0.4974 0.045 Uiso 1 1 calc R
C5 C 0.2215(3) -0.2915(3) 0.4730(3) 0.0476(7) Uani 1 1 d .
H5A H 0.1794 -0.3575 0.5268 0.071 Uiso 1 1 calc R
H5B H 0.3127 -0.3304 0.436 0.071 Uiso 1 1 calc R
H5C H 0.13 -0.2642 0.405 0.071 Uiso 1 1 calc R
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
S1 0.0251(3) 0.0380(4) 0.0288(3) -0.0034(3) 0.0002(2) -0.0019(2)
O1 0.0267(8) 0.0499(11) 0.0532(11) -0.0039(9) -0.0038(7) 0.0045(8)
O2 0.0391(9) 0.0458(10) 0.0283(8) -0.0094(8) 0.0031(7) -0.0062(8)
N1 0.0266(9) 0.0323(11) 0.0251(9) -0.0011(8) 0.0020(7) 0.0005(8)
N3 0.0341(11) 0.0406(12) 0.0365(12) -0.0014(10) 0.0119(9) -0.0020(9)
N2 0.0295(10) 0.0336(11) 0.0325(11) 0.0006(9) 0.0023(8) -0.0021(8)
N4 0.0384(11) 0.0391(13) 0.0250(10) -0.0037(9) 0.0056(8) -0.0105(10)
N5 0.0566(14) 0.0401(14) 0.0349(12) -0.0009(10) 0.0041(10) -0.0025(11)
C1 0.0303(11) 0.0269(12) 0.0268(11) 0.0009(9) 0.0009(9) 0.0008(9)
C3 0.0271(11) 0.0401(14) 0.0305(12) 0.0040(10) 0.0051(9) 0.0001(10)
C2 0.0299(11) 0.0368(13) 0.0273(12) 0.0018(10) 0.0068(9) 0.0040(10)
C4 0.0309(12) 0.0396(14) 0.0408(13) -0.0068(12) 0.0037(10) 0.0063(10)
C5 0.0490(15) 0.0388(15) 0.0555(17) -0.0123(13) 0.0106(13) 0.0025(12)
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 0 '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 0.006 '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
O1 S1 O2 122.21(10)
O1 S1 N1 108.26(10)
O2 S1 N1 105.70(10)
O1 S1 N3 103.95(11)
O2 S1 N3 110.76(11)
N1 S1 N3 104.75(10)
C2 N1 C1 107.11(18)
C2 N1 S1 124.53(16)
C1 N1 S1 127.98(15)
N4 N3 S1 112.30(15)
C1 N2 C3 106.65(19)
N5 N4 N3 173.4(2)
N2 C1 N1 109.63(19)
N2 C1 C4 127.5(2)
N1 C1 C4 122.9(2)
C2 C3 N2 111.8(2)
C2 C3 H3 124.1
N2 C3 H3 124.1
C3 C2 N1 104.8(2)
C3 C2 H2 127.6
N1 C2 H2 127.6
C1 C4 C5 112.6(2)
C1 C4 H4A 109.1
C5 C4 H4A 109.1
C1 C4 H4B 109.1
C5 C4 H4B 109.1
H4A C4 H4B 107.8
C4 C5 H5A 109.5
C4 C5 H5B 109.5
H5A C5 H5B 109.5
C4 C5 H5C 109.5
H5A C5 H5C 109.5
H5B C5 H5C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
S1 O1 1.4101(17)
S1 O2 1.4188(17)
S1 N1 1.6543(18)
S1 N3 1.657(2)
N1 C2 1.401(3)
N1 C1 1.407(3)
N3 N4 1.272(3)
N2 C1 1.301(3)
N2 C3 1.390(3)
N4 N5 1.111(3)
C1 C4 1.485(3)
C3 C2 1.339(3)
C3 H3 0.95
C2 H2 0.95
C4 C5 1.517(4)
C4 H4A 0.99
C4 H4B 0.99
C5 H5A 0.98
C5 H5B 0.98
C5 H5C 0.98
