data_IA-1190

_publ_section_acknowledgements
;
Crystal structure determination was performed in the Department of Structural
Studies of Zelinsky Institute of Organic Chemistry, Moscow.
;

_audit_creation_method            'SHELXL-2018/3'
_shelx_SHELXL_version_number      '2018/3'
_chemical_name_systematic         ?
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          'C10 H11 N5 O4 S'
_chemical_formula_sum             'C10 H11 N5 O4 S'
_chemical_formula_weight          297.30

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'
 
_space_group_crystal_system       orthorhombic
_space_group_IT_number            61
_space_group_name_H-M_alt         'P b c a'
_space_group_name_Hall            '-P 2ac 2ab'
 
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
 
loop_
 _space_group_symop_operation_xyz
 'x, y, z'
 'x+1/2, -y+1/2, -z'
 '-x, y+1/2, -z+1/2'
 '-x+1/2, -y, z+1/2'
 '-x, -y, -z'
 '-x-1/2, y-1/2, z'
 'x, -y-1/2, z-1/2'
 'x-1/2, y, -z-1/2'
 
_cell_length_a                    9.8425(2)
_cell_length_b                    12.4395(3)
_cell_length_c                    19.3468(4)
_cell_angle_alpha                 90
_cell_angle_beta                  90
_cell_angle_gamma                 90
_cell_volume                      2368.74(9)
_cell_formula_units_Z             8
_cell_measurement_temperature     100(2)
_cell_measurement_reflns_used      9822
_cell_measurement_theta_min        2.84
_cell_measurement_theta_max       38.54

_exptl_crystal_description        block
_exptl_crystal_colour             gold
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_density_diffrn     1.667
_exptl_crystal_F_000              1232
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           0.58
_exptl_crystal_size_mid           0.51
_exptl_crystal_size_min           0.45
_exptl_absorpt_coefficient_mu     0.298
_shelx_estimated_absorpt_T_min    0.846
_shelx_estimated_absorpt_T_max    0.878
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.6428
_exptl_absorpt_correction_T_max   0.6971
_exptl_absorpt_process_details
'SADABS 2016/2 (Krause et al., J. Appl. Cryst. 2015, 48, 3-10)'
_diffrn_ambient_temperature       100(2)
_diffrn_radiation_wavelength      0.71073
_diffrn_radiation_type            MoK\a
_diffrn_source                    'sealed X-Ray tube'
_diffrn_source_power              50
_diffrn_source_current            30
_diffrn_source_size               '0.6 mm, fine-focus'
_diffrn_radiation_monochromator   graphite
_diffrn_measurement_device_type   'Bruker AXS D8 QUEST, Photon III detector'
_diffrn_measurement_method        'φ and ω shutterless scans'
_diffrn_detector_area_resol_mean  7.31
_diffrn_reflns_number             93806
_diffrn_reflns_av_unetI/netI      0.0161
_diffrn_reflns_av_R_equivalents   0.0364
_diffrn_reflns_limit_h_min        -11
_diffrn_reflns_limit_h_max        16
_diffrn_reflns_limit_k_min        -21
_diffrn_reflns_limit_k_max        21
_diffrn_reflns_limit_l_min        -33
_diffrn_reflns_limit_l_max        33
_diffrn_reflns_theta_min          2.105
_diffrn_reflns_theta_max          37.799
_diffrn_reflns_theta_full         25.242
_diffrn_measured_fraction_theta_max   0.999
_diffrn_measured_fraction_theta_full  0.998
_diffrn_reflns_Laue_measured_fraction_max    0.999
_diffrn_reflns_Laue_measured_fraction_full   0.998
_diffrn_reflns_point_group_measured_fraction_max   0.999
_diffrn_reflns_point_group_measured_fraction_full  0.998
_reflns_number_total              6357
_reflns_number_gt                 5657
_reflns_threshold_expression      'I > 2σ(I)'
_reflns_Friedel_coverage          0.000
_reflns_Friedel_fraction_max      .
_reflns_Friedel_fraction_full     .
 
_reflns_special_details
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
 
_computing_data_collection        'APEX3 (Bruker, 2019)'
_computing_cell_refinement        'SAINT (Bruker, 2019)'
_computing_data_reduction         'SAINT (Bruker, 2019)'
_computing_structure_solution
 'SHELXT, SHELXS-2013 (Sheldrick, Acta Cryst., 2015, A71, 3-8)'
_computing_structure_refinement
 'SHELXL-2018 (Sheldrick, Acta Cryst., 2015, C71, 3-8)'
_computing_molecular_graphics
 'SHELXTL (Sheldrick, Acta Cryst., 2008, A64, 112-122)'
_computing_publication_material
 'SHELXTL (Sheldrick, Acta Cryst., 2008, A64, 112-122)'
_refine_special_details
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger.
;
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0413P)²+1.0101P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      direct
_atom_sites_solution_secondary    difmap
_atom_sites_solution_hydrogens    difmap
_refine_ls_hydrogen_treatment     refall
_refine_ls_extinction_method      none
_refine_ls_extinction_coef        .
_refine_ls_number_reflns          6357
_refine_ls_number_parameters      225
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0404
_refine_ls_R_factor_gt            0.0344
_refine_ls_wR_factor_ref          0.0928
_refine_ls_wR_factor_gt           0.0884
_refine_ls_goodness_of_fit_ref    1.093
_refine_ls_restrained_S_all       1.093
_refine_ls_shift/su_max           0.001
_refine_ls_shift/su_mean          0.000
 
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_site_symmetry_order  
 _atom_site_calc_flag
 _atom_site_refinement_flags_posn
 _atom_site_refinement_flags_adp
 _atom_site_refinement_flags_occupancy
 _atom_site_disorder_assembly
 _atom_site_disorder_group
S1 S 0.50922(2) 0.71147(2) 0.60884(2) 0.01305(5) Uani 1 1 d . . . . .
O1 O 0.23816(6) 0.77993(5) 0.59766(3) 0.01484(10) Uani 1 1 d . . . . .
H1 H 0.156(2) 0.8058(16) 0.5917(10) 0.051(5) Uiso 1 1 d . . . . .
O2 O 0.15038(6) 0.64071(5) 0.53787(3) 0.01433(10) Uani 1 1 d . . . . .
O3 O 0.50163(6) 0.36066(5) 0.58728(3) 0.01284(10) Uani 1 1 d . . . . .
O4 O 0.86620(7) 0.47233(6) 0.78497(3) 0.01820(11) Uani 1 1 d . . . . .
N1 N 0.62748(6) 0.51147(5) 0.59986(3) 0.01028(10) Uani 1 1 d . . . . .
N2 N 0.75696(7) 0.41178(5) 0.68662(3) 0.01341(11) Uani 1 1 d . . . . .
N3 N 0.90643(7) 0.54538(6) 0.67648(3) 0.01309(11) Uani 1 1 d . . . . .
N4 N 0.86010(6) 0.59575(5) 0.55617(3) 0.01231(10) Uani 1 1 d . . . . .
H4 H 0.9329(16) 0.6322(12) 0.5504(8) 0.024(4) Uiso 1 1 d . . . . .
N5 N 0.75425(6) 0.66694(5) 0.56944(3) 0.01226(10) Uani 1 1 d . . . . .
C1 C 0.24302(7) 0.68442(6) 0.56836(4) 0.01106(11) Uani 1 1 d . . . . .
C2 C 0.37754(7) 0.63080(6) 0.57883(4) 0.01077(11) Uani 1 1 d . . . . .
C3 C 0.38786(7) 0.52447(6) 0.56802(4) 0.01092(11) Uani 1 1 d . . . . .
H3 H 0.3102(15) 0.4847(11) 0.5523(7) 0.021(3) Uiso 1 1 d . . . . .
C4 C 0.50735(7) 0.46027(6) 0.58565(4) 0.01027(10) Uani 1 1 d . . . . .
C5 C 0.74907(7) 0.44287(6) 0.61515(4) 0.01055(10) Uani 1 1 d . . . . .
H5 H 0.7406(14) 0.3822(11) 0.5852(7) 0.016(3) Uiso 1 1 d . . . . .
C6 C 0.84517(8) 0.47620(6) 0.72273(4) 0.01299(11) Uani 1 1 d . . . . .
C7 C 0.87897(7) 0.50989(6) 0.60567(4) 0.01100(11) Uani 1 1 d . . . . .
H7 H 0.9525(14) 0.4671(10) 0.5885(7) 0.013(3) Uiso 1 1 d . . . . .
C8 C 0.64393(7) 0.62330(6) 0.59016(4) 0.01077(11) Uani 1 1 d . . . . .
C9 C 0.67121(9) 0.33264(7) 0.72031(4) 0.01694(13) Uani 1 1 d . . . . .
H9A H 0.7018(15) 0.3212(12) 0.7655(8) 0.022(3) Uiso 1 1 d . . . . .
H9B H 0.6755(16) 0.2666(13) 0.6953(8) 0.032(4) Uiso 1 1 d . . . . .
H9C H 0.5781(17) 0.3570(13) 0.7226(9) 0.032(4) Uiso 1 1 d . . . . .
C10 C 1.03475(9) 0.59593(8) 0.69448(4) 0.01811(14) Uani 1 1 d . . . . .
H10A H 1.1115(15) 0.5519(12) 0.6802(8) 0.025(4) Uiso 1 1 d . . . . .
H10B H 1.0380(15) 0.6029(12) 0.7441(8) 0.025(3) Uiso 1 1 d . . . . .
H10C H 1.0426(16) 0.6675(12) 0.6715(8) 0.025(4) Uiso 1 1 d . . . . .
 
 
_geom_special_details
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
 
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 C2 1.7390(7) . ?
S1 C8 1.7584(7) . ?
O1 C1 1.3173(9) . ?
O1 H1 0.88(2) . ?
O2 C1 1.2144(9) . ?
O3 C4 1.2408(9) . ?
O4 C6 1.2229(9) . ?
N1 C4 1.3709(9) . ?
N1 C8 1.4129(9) . ?
N1 C5 1.4993(9) . ?
N2 C6 1.3726(10) . ?
N2 C5 1.4379(10) . ?
N2 C9 1.4512(10) . ?
N3 C6 1.3801(10) . ?
N3 C10 1.4531(11) . ?
N3 C7 1.4645(10) . ?
N4 N5 1.3912(9) . ?
N4 C7 1.4465(10) . ?
N4 H4 0.855(15) . ?
N5 C8 1.2785(9) . ?
C1 C2 1.4962(10) . ?
C2 C3 1.3430(10) . ?
C3 C4 1.4619(10) . ?
C3 H3 0.960(15) . ?
C5 C7 1.5373(10) . ?
C5 H5 0.955(14) . ?
C7 H7 0.958(14) . ?
C9 H9A 0.935(15) . ?
C9 H9B 0.955(17) . ?
C9 H9C 0.967(17) . ?
C10 H10A 0.973(15) . ?
C10 H10B 0.964(16) . ?
C10 H10C 0.999(15) . ?
 
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
C2 S1 C8 97.66(3) . . ?
C1 O1 H1 107.9(13) . . ?
C4 N1 C8 121.98(6) . . ?
C4 N1 C5 117.62(6) . . ?
C8 N1 C5 119.68(6) . . ?
C6 N2 C5 111.50(6) . . ?
C6 N2 C9 122.37(7) . . ?
C5 N2 C9 125.66(7) . . ?
C6 N3 C10 119.62(6) . . ?
C6 N3 C7 109.75(6) . . ?
C10 N3 C7 121.00(6) . . ?
N5 N4 C7 116.36(6) . . ?
N5 N4 H4 108.3(10) . . ?
C7 N4 H4 111.7(10) . . ?
C8 N5 N4 115.06(6) . . ?
O2 C1 O1 125.84(7) . . ?
O2 C1 C2 122.04(7) . . ?
O1 C1 C2 112.08(6) . . ?
C3 C2 C1 119.01(6) . . ?
C3 C2 S1 124.33(6) . . ?
C1 C2 S1 116.58(5) . . ?
C2 C3 C4 124.23(6) . . ?
C2 C3 H3 119.8(9) . . ?
C4 C3 H3 115.7(9) . . ?
O3 C4 N1 119.87(6) . . ?
O3 C4 C3 121.00(6) . . ?
N1 C4 C3 119.13(6) . . ?
N2 C5 N1 112.71(6) . . ?
N2 C5 C7 102.46(6) . . ?
N1 C5 C7 109.37(6) . . ?
N2 C5 H5 112.0(8) . . ?
N1 C5 H5 105.1(8) . . ?
C7 C5 H5 115.4(8) . . ?
O4 C6 N2 125.82(7) . . ?
O4 C6 N3 126.09(7) . . ?
N2 C6 N3 108.09(6) . . ?
N4 C7 N3 114.86(6) . . ?
N4 C7 C5 111.88(6) . . ?
N3 C7 C5 101.85(6) . . ?
N4 C7 H7 106.1(8) . . ?
N3 C7 H7 110.7(8) . . ?
C5 C7 H7 111.6(8) . . ?
N5 C8 N1 123.85(7) . . ?
N5 C8 S1 116.10(5) . . ?
N1 C8 S1 120.03(5) . . ?
N2 C9 H9A 109.6(9) . . ?
N2 C9 H9B 109.4(10) . . ?
H9A C9 H9B 109.1(13) . . ?
N2 C9 H9C 111.1(10) . . ?
H9A C9 H9C 108.1(13) . . ?
H9B C9 H9C 109.6(13) . . ?
N3 C10 H10A 111.3(9) . . ?
N3 C10 H10B 107.8(9) . . ?
H10A C10 H10B 107.9(13) . . ?
N3 C10 H10C 110.3(9) . . ?
H10A C10 H10C 108.4(12) . . ?
H10B C10 H10C 111.1(12) . . ?
 
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
C7 N4 N5 C8 -42.32(9) . . . . ?
O2 C1 C2 C3 -14.72(11) . . . . ?
O1 C1 C2 C3 163.19(7) . . . . ?
O2 C1 C2 S1 168.45(6) . . . . ?
O1 C1 C2 S1 -13.64(8) . . . . ?
C8 S1 C2 C3 17.93(7) . . . . ?
C8 S1 C2 C1 -165.42(6) . . . . ?
C1 C2 C3 C4 -170.99(6) . . . . ?
S1 C2 C3 C4 5.58(11) . . . . ?
C8 N1 C4 O3 171.77(7) . . . . ?
C5 N1 C4 O3 1.57(10) . . . . ?
C8 N1 C4 C3 -7.58(10) . . . . ?
C5 N1 C4 C3 -177.78(6) . . . . ?
C2 C3 C4 O3 165.61(7) . . . . ?
C2 C3 C4 N1 -15.04(11) . . . . ?
C6 N2 C5 N1 -98.82(7) . . . . ?
C9 N2 C5 N1 73.37(9) . . . . ?
C6 N2 C5 C7 18.61(8) . . . . ?
C9 N2 C5 C7 -169.20(7) . . . . ?
C4 N1 C5 N2 -85.46(8) . . . . ?
C8 N1 C5 N2 104.10(7) . . . . ?
C4 N1 C5 C7 161.27(6) . . . . ?
C8 N1 C5 C7 -9.17(8) . . . . ?
C5 N2 C6 O4 175.63(8) . . . . ?
C9 N2 C6 O4 3.14(13) . . . . ?
C5 N2 C6 N3 -4.78(9) . . . . ?
C9 N2 C6 N3 -177.27(7) . . . . ?
C10 N3 C6 O4 20.71(12) . . . . ?
C7 N3 C6 O4 167.16(8) . . . . ?
C10 N3 C6 N2 -158.88(7) . . . . ?
C7 N3 C6 N2 -12.43(8) . . . . ?
N5 N4 C7 N3 -59.47(8) . . . . ?
N5 N4 C7 C5 55.99(8) . . . . ?
C6 N3 C7 N4 144.07(6) . . . . ?
C10 N3 C7 N4 -70.02(9) . . . . ?
C6 N3 C7 C5 22.95(8) . . . . ?
C10 N3 C7 C5 168.86(7) . . . . ?
N2 C5 C7 N4 -147.22(6) . . . . ?
N1 C5 C7 N4 -27.43(8) . . . . ?
N2 C5 C7 N3 -24.05(7) . . . . ?
N1 C5 C7 N3 95.74(6) . . . . ?
N4 N5 C8 N1 0.40(10) . . . . ?
N4 N5 C8 S1 178.90(5) . . . . ?
C4 N1 C8 N5 -144.29(7) . . . . ?
C5 N1 C8 N5 25.72(11) . . . . ?
C4 N1 C8 S1 37.27(9) . . . . ?
C5 N1 C8 S1 -152.72(5) . . . . ?
C2 S1 C8 N5 143.42(6) . . . . ?
C2 S1 C8 N1 -38.03(6) . . . . ?
 
loop_
 _geom_hbond_atom_site_label_D 
 _geom_hbond_atom_site_label_H 
 _geom_hbond_atom_site_label_A 
 _geom_hbond_distance_DH 
 _geom_hbond_distance_HA 
 _geom_hbond_distance_DA 
 _geom_hbond_angle_DHA 
 _geom_hbond_site_symmetry_A 
 _geom_hbond_publ_flag
O1 H1 O3  0.88(2) 1.70(2) 2.5728(8) 175(2) 6_665 yes
N4 H4 O2  0.855(15) 2.157(15) 2.9328(9) 150.8(14) 1_655 yes
 
_refine_diff_density_max    0.631
_refine_diff_density_min   -0.387
_refine_diff_density_rms    0.067



