 
data_dal_195
 
_audit_creation_method            'SHELXL-2018/3'
_shelx_SHELXL_version_number      '2018/3'
_chemical_name_systematic         ?
_chemical_name_common             ?
_chemical_melting_point           ?
_chemical_formula_moiety          'C17 H15 N5 O4 S'
_chemical_formula_sum
 'C17 H15 N5 O4 S' 
_chemical_formula_weight          385.40

loop_
 _atom_type_symbol
 _atom_type_description
 _atom_type_scat_dispersion_real
 _atom_type_scat_dispersion_imag
 _atom_type_scat_source
 'C'  'C'   0.0181   0.0091
 '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'   0.0311   0.0180
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O'  'O'   0.0492   0.0322
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'S'  'S'   0.3331   0.5567
 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 
_space_group_crystal_system       triclinic
_space_group_IT_number            2
_space_group_name_H-M_alt         'P -1'
_space_group_name_Hall            '-P 1'
 
_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, -y, -z'
 
_cell_length_a                    6.9122(2)
_cell_length_b                    8.46912(17)
_cell_length_c                    15.3541(7)
_cell_angle_alpha                 91.186(3)
_cell_angle_beta                  102.063(3)
_cell_angle_gamma                 99.164(2)
_cell_volume                      866.41(5)
_cell_formula_units_Z             2
_cell_measurement_temperature     150(2)
_cell_measurement_reflns_used     11387  
_cell_measurement_theta_min       2.9440 
_cell_measurement_theta_max       76.4770
 
_exptl_crystal_description        'block'
_exptl_crystal_colour             'colourless'
_exptl_crystal_density_meas       ?
_exptl_crystal_density_method     ?
_exptl_crystal_density_diffrn     1.477          
_exptl_crystal_F_000              400
_exptl_transmission_factor_min    ?
_exptl_transmission_factor_max    ?
_exptl_crystal_size_max           0.06
_exptl_crystal_size_mid           0.05
_exptl_crystal_size_min           0.04
_exptl_absorpt_coefficient_mu     1.983
_shelx_estimated_absorpt_T_min    ?
_shelx_estimated_absorpt_T_max    ?
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_correction_T_min   0.82290
_exptl_absorpt_correction_T_max   1.00000
_exptl_absorpt_process_details    
;
CrysAlisPro 1.171.41.123a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details    ?
_diffrn_ambient_temperature       150(2)
_diffrn_radiation_wavelength      1.54184
_diffrn_radiation_type            CuK\a
_diffrn_source                    'micro-focus sealed X-ray tube'   
_diffrn_measurement_device_type   'XtaLAB Synergy, Dualflex, HyPix' 
_diffrn_measurement_method        'ω scans'                        
_diffrn_detector_area_resol_mean  ?
_diffrn_reflns_number             15849
_diffrn_reflns_av_unetI/netI      0.0221
_diffrn_reflns_av_R_equivalents   0.0335
_diffrn_reflns_limit_h_min        -8
_diffrn_reflns_limit_h_max        8
_diffrn_reflns_limit_k_min        -10
_diffrn_reflns_limit_k_max        10
_diffrn_reflns_limit_l_min        -19
_diffrn_reflns_limit_l_max        15
_diffrn_reflns_theta_min          2.948
_diffrn_reflns_theta_max          77.052
_diffrn_reflns_theta_full         67.684
_diffrn_measured_fraction_theta_max   0.949
_diffrn_measured_fraction_theta_full  0.998
_diffrn_reflns_Laue_measured_fraction_max    0.949
_diffrn_reflns_Laue_measured_fraction_full   0.998
_diffrn_reflns_point_group_measured_fraction_max   0.949
_diffrn_reflns_point_group_measured_fraction_full  0.998
_reflns_number_total              3481
_reflns_number_gt                 3183
_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        'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_cell_refinement        'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_reduction         'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_structure_solution     'SHELXT 2014/4 (Sheldrick, 2014)'
_computing_structure_refinement 'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics     ?
_computing_publication_material   ?
_refine_special_details           ?
_refine_ls_structure_factor_coef  Fsqd
_refine_ls_matrix_type            full
_refine_ls_weighting_scheme       calc
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0637P)²+0.2044P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary      ?
_atom_sites_solution_secondary    ?
_atom_sites_solution_hydrogens    geom
_refine_ls_hydrogen_treatment     constr
_refine_ls_extinction_method      'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef        0.0013(5)
_refine_ls_extinction_expression
 'Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^'
_refine_ls_number_reflns          3481
_refine_ls_number_parameters      248
_refine_ls_number_restraints      6
_refine_ls_R_factor_all           0.0380
_refine_ls_R_factor_gt            0.0358
_refine_ls_wR_factor_ref          0.1051
_refine_ls_wR_factor_gt           0.1036
_refine_ls_goodness_of_fit_ref    1.083
_refine_ls_restrained_S_all       1.082
_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
S11 S 0.31172(5) 0.98727(4) 0.73978(2) 0.02781(13) Uani 1 1 d . . . . .
O13 O 0.18470(17) 1.07885(12) 0.68293(7) 0.0325(3) Uani 1 1 d . . . . .
O16 O 0.22586(15) 0.23519(11) 0.40313(6) 0.0268(2) Uani 1 1 d . . . . .
N10 N 0.39302(17) 0.69340(14) 0.72969(8) 0.0259(3) Uani 1 1 d . . . . .
O14 O 0.11363(15) 0.47237(12) 0.31993(6) 0.0281(2) Uani 1 1 d . . . . .
O12 O 0.51575(17) 1.05804(13) 0.77904(8) 0.0400(3) Uani 1 1 d . . . . .
N2 N 0.25388(17) 0.80294(13) 0.59151(8) 0.0246(3) Uani 1 1 d . . . . .
C8 C 0.32088(19) 0.52994(16) 0.59280(9) 0.0223(3) Uani 1 1 d . . . . .
C6 C 0.24216(19) 0.36845(15) 0.45575(9) 0.0226(3) Uani 1 1 d . . . . .
C4 C 0.18660(19) 0.64609(16) 0.45354(9) 0.0236(3) Uani 1 1 d . . . . .
H4 H 0.144925 0.734380 0.421951 0.028 Uiso 1 1 calc R U . . .
C7 C 0.30987(19) 0.38180(16) 0.54620(9) 0.0228(3) Uani 1 1 d . . . . .
H7 H 0.349178 0.292518 0.577498 0.027 Uiso 1 1 calc R U . . .
C21 C 0.1936(2) 0.91498(17) 0.82563(9) 0.0290(3) Uani 1 1 d . . . . .
C1 C 0.3191(2) 0.80588(16) 0.67747(9) 0.0246(3) Uani 1 1 d . . . . .
N18 N 0.46257(19) 0.42910(15) 0.73175(8) 0.0293(3) Uani 1 1 d . U . . .
C5 C 0.17951(19) 0.50315(16) 0.40847(9) 0.0228(3) Uani 1 1 d . . . . .
C9 C 0.39215(19) 0.55703(16) 0.68586(9) 0.0237(3) Uani 1 1 d . . . . .
C3 C 0.25585(19) 0.66164(15) 0.54678(9) 0.0226(3) Uani 1 1 d . . . . .
C17 C 0.2599(2) 0.09205(16) 0.44808(10) 0.0309(3) Uani 1 1 d . . . . .
H17A H 0.238413 0.002181 0.403984 0.046 Uiso 1 1 calc R U . . .
H17B H 0.166519 0.069249 0.487997 0.046 Uiso 1 1 calc R U . . .
H17C H 0.398143 0.106967 0.482970 0.046 Uiso 1 1 calc R U . . .
N19 N 0.5100(2) 0.45122(16) 0.81442(9) 0.0374(3) Uani 1 1 d . U . . .
C26 C -0.0142(2) 0.88214(19) 0.80937(10) 0.0335(3) Uani 1 1 d . . . . .
H26 H -0.092287 0.898487 0.752587 0.040 Uiso 1 1 calc R U . . .
C22 C 0.3089(3) 0.8906(2) 0.90804(11) 0.0400(4) Uani 1 1 d . . . . .
H22 H 0.451191 0.912584 0.918615 0.048 Uiso 1 1 calc R U . . .
C25 C -0.1067(3) 0.8250(2) 0.87726(11) 0.0381(4) Uani 1 1 d . . . . .
H25 H -0.249077 0.802844 0.866487 0.046 Uiso 1 1 calc R U . . .
C24 C 0.0047(3) 0.79967(19) 0.96047(11) 0.0389(4) Uani 1 1 d . . . . .
C15 C 0.0636(2) 0.60405(19) 0.26707(10) 0.0329(3) Uani 1 1 d . . . . .
H15A H 0.012824 0.565583 0.204557 0.049 Uiso 1 1 calc R U . . .
H15B H 0.183699 0.685572 0.271920 0.049 Uiso 1 1 calc R U . . .
H15C H -0.039673 0.650789 0.288671 0.049 Uiso 1 1 calc R U . . .
C27 C -0.0971(4) 0.7372(2) 1.03394(12) 0.0532(5) Uani 1 1 d . . . . .
H27A H -0.236627 0.755047 1.020540 0.080 Uiso 1 1 calc R U . . .
H27B H -0.026399 0.793859 1.090787 0.080 Uiso 1 1 calc R U . . .
H27C H -0.094151 0.622287 1.038115 0.080 Uiso 1 1 calc R U . . .
C23 C 0.2131(3) 0.8335(2) 0.97501(11) 0.0446(4) Uani 1 1 d . . . . .
H23 H 0.291320 0.817154 1.031763 0.054 Uiso 1 1 calc R U . . .
N20 N 0.5579(3) 0.4525(2) 0.88860(11) 0.0620(5) Uani 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
S11 O13 1.4348(11) . ?
S11 O12 1.4395(12) . ?
S11 C21 1.7615(15) . ?
S11 C1 1.8061(14) . ?
O16 C6 1.3501(16) . ?
O16 C17 1.4349(16) . ?
N10 C9 1.3232(18) . ?
N10 C1 1.3517(17) . ?
O14 C5 1.3462(16) . ?
O14 C15 1.4369(16) . ?
N2 C1 1.3008(18) . ?
N2 C3 1.3707(17) . ?
C8 C9 1.4118(19) . ?
C8 C7 1.4148(18) . ?
C8 C3 1.4159(18) . ?
C6 C7 1.3659(19) . ?
C6 C5 1.4409(17) . ?
C4 C5 1.3707(19) . ?
C4 C3 1.4078(19) . ?
C21 C22 1.386(2) . ?
C21 C26 1.387(2) . ?
N18 N19 1.2451(18) . ?
N18 C9 1.4013(17) . ?
N19 N20 1.117(2) . ?
C26 C25 1.389(2) . ?
C22 C23 1.390(3) . ?
C25 C24 1.387(2) . ?
C24 C23 1.392(3) . ?
C24 C27 1.512(2) . ?
 
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
O13 S11 O12 119.62(7) . . ?
O13 S11 C21 109.23(7) . . ?
O12 S11 C21 108.46(7) . . ?
O13 S11 C1 108.00(6) . . ?
O12 S11 C1 107.43(7) . . ?
C21 S11 C1 102.79(7) . . ?
C6 O16 C17 116.24(11) . . ?
C9 N10 C1 114.07(11) . . ?
C5 O14 C15 117.33(11) . . ?
C1 N2 C3 114.89(11) . . ?
C9 C8 C7 123.75(12) . . ?
C9 C8 C3 115.76(12) . . ?
C7 C8 C3 120.48(12) . . ?
O16 C6 C7 125.47(12) . . ?
O16 C6 C5 114.21(12) . . ?
C7 C6 C5 120.31(12) . . ?
C5 C4 C3 119.78(12) . . ?
C6 C7 C8 119.33(12) . . ?
C22 C21 C26 120.91(15) . . ?
C22 C21 S11 119.79(13) . . ?
C26 C21 S11 119.30(11) . . ?
N2 C1 N10 130.43(12) . . ?
N2 C1 S11 116.53(10) . . ?
N10 C1 S11 113.04(10) . . ?
N19 N18 C9 115.15(12) . . ?
O14 C5 C4 125.49(12) . . ?
O14 C5 C6 113.95(11) . . ?
C4 C5 C6 120.56(12) . . ?
N10 C9 N18 120.24(12) . . ?
N10 C9 C8 123.47(12) . . ?
N18 C9 C8 116.29(12) . . ?
N2 C3 C4 119.20(12) . . ?
N2 C3 C8 121.28(12) . . ?
C4 C3 C8 119.49(12) . . ?
N20 N19 N18 171.42(16) . . ?
C21 C26 C25 119.09(14) . . ?
C21 C22 C23 119.01(17) . . ?
C24 C25 C26 121.29(16) . . ?
C25 C24 C23 118.46(15) . . ?
C25 C24 C27 120.97(17) . . ?
C23 C24 C27 120.57(16) . . ?
C22 C23 C24 121.24(15) . . ?
 
_refine_diff_density_max    0.319
_refine_diff_density_min   -0.447
_refine_diff_density_rms    0.049




# start Validation Reply Form
_vrf_PLAT230_dal_195
;
PROBLEM:  Hirshfeld Test Diff for N18 --N19 . 10.5 s.u.
RESPONSE: Large differences in anisotropic displacement parameters   
along chemical bond N18-N19 may be related to contamination of these 
parameters with other unresolved effects. 
;
# end Validation Reply Form
