# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_A_100
_database_code_depnum_ccdc_archive 'CCDC 1821383'
_audit_update_record             
;
2018-02-01 deposited with the CCDC.
2018-11-08 downloaded from the CCDC.
;
_audit_creation_date             2016-04-18
_audit_creation_method           SHELXL-2016/6
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.5
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
#------------------ CHEMICAL INFORMATION ------------------------------------# 
_chemical_name_systematic        
3-Diethylamino-4-(4-methoxyphenyl)-1,1-dioxo-4H-1λ⁶,2-thiazete-4-carbonitrile
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H17 N3 O3 S'
_chemical_formula_sum            'C14 H17 N3 O3 S'
_chemical_formula_weight         307.36

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.54290(10)
_cell_length_b                   13.2378(2)
_cell_length_c                   13.0463(2)
_cell_angle_alpha                90
_cell_angle_beta                 95.0916(6)
_cell_angle_gamma                90
_cell_volume                     1469.57(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7475
_cell_measurement_theta_min      2.196
_cell_measurement_theta_max      27.4895

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.389
_exptl_crystal_F_000             648
_exptl_transmission_factor_min   0.8996
_exptl_transmission_factor_max   0.9391
_exptl_crystal_size_max          0.275
_exptl_crystal_size_mid          0.179
_exptl_crystal_size_min          0.125
_exptl_absorpt_coefficient_mu    0.234
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.8996
_exptl_absorpt_correction_T_max  0.9391
_exptl_absorpt_process_details   'SADABS-2007/4, Bruker'
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed X-ray tube'
_diffrn_measurement_device_type  'Bruker AXS Smart APEX'
_diffrn_measurement_method       ω-scan
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21351
_diffrn_reflns_av_unetI/netI     0.0182
_diffrn_reflns_av_R_equivalents  0.0264
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.196
_diffrn_reflns_theta_max         27.549
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3383
_reflns_number_gt                2923
_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       'Saint+(Bruker, 2007/4)'
_computing_cell_refinement       'Saint+(Bruker, 2007/4)'
_computing_data_reduction        'Saint+(Bruker, 2007/4)'
_computing_structure_solution    'SHELXS-2016 (Sheldrick, 2016)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.0553P)²+0.8073P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   direct
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3383
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0430
_refine_ls_R_factor_gt           0.0359
_refine_ls_wR_factor_ref         0.1002
_refine_ls_wR_factor_gt          0.0936
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_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 0.16797(4) 0.56105(3) 0.71096(3) 0.01676(11) Uani 1 1 d . . . . .
N1 N 0.47027(14) 0.68268(9) 0.59403(9) 0.0161(2) Uani 1 1 d . . . . .
C10 C 0.17443(16) 0.55624(10) 0.49716(11) 0.0168(3) Uani 1 1 d . . . . .
C7 C 0.08395(16) 0.72048(10) 0.56418(11) 0.0152(3) Uani 1 1 d . . . . .
C8 C 0.18367(16) 0.62721(10) 0.58337(11) 0.0156(3) Uani 1 1 d . . . . .
O1 O -0.22776(13) 0.96009(8) 0.52696(9) 0.0240(2) Uani 1 1 d . . . . .
O3 O 0.06757(12) 0.61276(8) 0.77571(8) 0.0223(2) Uani 1 1 d . . . . .
N2 N 0.35289(14) 0.59895(9) 0.72777(9) 0.0186(3) Uani 1 1 d . . . . .
C9 C 0.35106(16) 0.63985(10) 0.63464(11) 0.0159(3) Uani 1 1 d . . . . .
C2 C -0.11689(17) 0.88608(11) 0.54144(11) 0.0179(3) Uani 1 1 d . . . . .
N3 N 0.16979(15) 0.49987(9) 0.43037(10) 0.0226(3) Uani 1 1 d . . . . .
C3 C -0.13432(17) 0.80578(11) 0.47209(11) 0.0175(3) Uani 1 1 d . . . . .
H3 H -0.2144(15) 0.80796(11) 0.4163(11) 0.021 Uiso 1 1 calc R U . . .
C4 C -0.03561(16) 0.72302(11) 0.48415(11) 0.0162(3) Uani 1 1 d . . . . .
H4 H -0.0491(3) 0.6684(11) 0.4383(9) 0.019 Uiso 1 1 calc R U . . .
C5 C 0.00630(17) 0.88647(11) 0.61884(11) 0.0191(3) Uani 1 1 d . . . . .
H5 H 0.0216(4) 0.9416(11) 0.6630(9) 0.023 Uiso 1 1 calc R U . . .
C6 C 0.10615(17) 0.80344(11) 0.62945(11) 0.0177(3) Uani 1 1 d . . . . .
H6 H 0.1890(17) 0.80333(11) 0.6809(10) 0.021 Uiso 1 1 calc R U . . .
O2 O 0.15612(12) 0.45295(8) 0.70289(8) 0.0214(2) Uani 1 1 d . . . . .
C11 C 0.62190(17) 0.69202(11) 0.65659(11) 0.0196(3) Uani 1 1 d . . . . .
H11A H 0.7070(11) 0.69448(12) 0.6112(6) 0.023 Uiso 1 1 calc R U . . .
H11B H 0.6382(3) 0.6326(8) 0.7008(6) 0.023 Uiso 1 1 calc R U . . .
C14 C 0.52697(18) 0.65263(12) 0.41271(12) 0.0235(3) Uani 1 1 d . . . . .
H14A H 0.5165(2) 0.6825(4) 0.3453(8) 0.035 Uiso 1 1 calc R U . . .
H14B H 0.6363(12) 0.64123(18) 0.4336(3) 0.035 Uiso 1 1 calc R U . . .
H14C H 0.4715(6) 0.5894(7) 0.41120(12) 0.035 Uiso 1 1 calc R U . . .
C13 C 0.45824(17) 0.72358(11) 0.48879(11) 0.0189(3) Uani 1 1 d . . . . .
H13A H 0.5135(7) 0.7882(8) 0.48890(11) 0.023 Uiso 1 1 calc R U . . .
H13B H 0.3477(14) 0.7360(2) 0.4664(3) 0.023 Uiso 1 1 calc R U . . .
C1 C -0.2265(2) 1.03771(12) 0.60360(14) 0.0272(4) Uani 1 1 d . . . . .
H1A H -0.3106(10) 1.0858(6) 0.5848(3) 0.041 Uiso 1 1 calc R U . . .
H1B H -0.2425(3) 1.0075(4) 0.6700(8) 0.041 Uiso 1 1 calc R U . . .
H1C H -0.1256(12) 1.0726(4) 0.60809(15) 0.041 Uiso 1 1 calc R U . . .
C12 C 0.6269(2) 0.78618(14) 0.72249(14) 0.0308(4) Uani 1 1 d . . . . .
H12A H 0.7284(12) 0.79038(15) 0.7630(5) 0.046 Uiso 1 1 calc R U . . .
H12B H 0.6124(3) 0.8456(7) 0.6784(5) 0.046 Uiso 1 1 calc R U . . .
H12C H 0.5431(10) 0.78330(14) 0.7686(6) 0.046 Uiso 1 1 calc R U . . .


_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 O3 1.4305(11) . ?
S1 O2 1.4379(11) . ?
S1 N2 1.6534(12) . ?
S1 C8 1.8962(14) . ?
S1 C9 2.1914(15) . ?
N1 C9 1.3172(18) . ?
N1 C13 1.4710(18) . ?
N1 C11 1.4737(18) . ?
C10 N3 1.1452(19) . ?
C10 C8 1.4622(19) . ?
C7 C6 1.3923(19) . ?
C7 C4 1.3946(19) . ?
C7 C8 1.5083(19) . ?
C8 C9 1.5332(19) . ?
O1 C2 1.3642(17) . ?
O1 C1 1.4331(19) . ?
N2 C9 1.3290(18) . ?
C2 C5 1.392(2) . ?
C2 C3 1.395(2) . ?
C3 C4 1.383(2) . ?
C3 H3 0.954(18) . ?
C4 H4 0.939(18) . ?
C5 C6 1.391(2) . ?
C5 H5 0.932(19) . ?
C6 H6 0.932(18) . ?
C11 C12 1.513(2) . ?
C11 H11A 0.978(13) . ?
C11 H11B 0.978(13) . ?
C14 C13 1.522(2) . ?
C14 H14A 0.962(11) . ?
C14 H14B 0.962(11) . ?
C14 H14C 0.962(11) . ?
C13 H13A 0.977(13) . ?
C13 H13B 0.977(13) . ?
C1 H1A 0.975(12) . ?
C1 H1B 0.975(12) . ?
C1 H1C 0.975(12) . ?
C12 H12A 0.976(12) . ?
C12 H12B 0.976(12) . ?
C12 H12C 0.976(12) . ?

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
O3 S1 O2 118.52(7) . . ?
O3 S1 N2 113.10(7) . . ?
O2 S1 N2 111.84(7) . . ?
O3 S1 C8 112.97(6) . . ?
O2 S1 C8 113.92(6) . . ?
N2 S1 C8 80.51(6) . . ?
O3 S1 C9 122.01(6) . . ?
O2 S1 C9 119.27(6) . . ?
N2 S1 C9 37.23(6) . . ?
C8 S1 C9 43.31(5) . . ?
C9 N1 C13 122.78(12) . . ?
C9 N1 C11 119.10(12) . . ?
C13 N1 C11 118.11(11) . . ?
N3 C10 C8 178.72(16) . . ?
C6 C7 C4 119.33(13) . . ?
C6 C7 C8 119.99(13) . . ?
C4 C7 C8 120.62(12) . . ?
C10 C8 C7 114.03(12) . . ?
C10 C8 C9 112.98(11) . . ?
C7 C8 C9 118.31(12) . . ?
C10 C8 S1 112.04(10) . . ?
C7 C8 S1 116.16(10) . . ?
C9 C8 S1 78.65(8) . . ?
C2 O1 C1 117.14(12) . . ?
C9 N2 S1 93.95(9) . . ?
N1 C9 N2 126.61(13) . . ?
N1 C9 C8 126.58(13) . . ?
N2 C9 C8 106.81(12) . . ?
N1 C9 S1 174.95(11) . . ?
N2 C9 S1 48.82(7) . . ?
C8 C9 S1 58.04(7) . . ?
O1 C2 C5 124.65(13) . . ?
O1 C2 C3 115.12(13) . . ?
C5 C2 C3 120.23(13) . . ?
C4 C3 C2 120.06(13) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C4 C7 120.19(13) . . ?
C3 C4 H4 119.9 . . ?
C7 C4 H4 119.9 . . ?
C6 C5 C2 119.12(13) . . ?
C6 C5 H5 120.4 . . ?
C2 C5 H5 120.4 . . ?
C5 C6 C7 120.90(13) . . ?
C5 C6 H6 119.6 . . ?
C7 C6 H6 119.6 . . ?
N1 C11 C12 111.28(13) . . ?
N1 C11 H11A 109.4 . . ?
C12 C11 H11A 109.4 . . ?
N1 C11 H11B 109.4 . . ?
C12 C11 H11B 109.4 . . ?
H11A C11 H11B 108.0 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N1 C13 C14 112.50(12) . . ?
N1 C13 H13A 109.1 . . ?
C14 C13 H13A 109.1 . . ?
N1 C13 H13B 109.1 . . ?
C14 C13 H13B 109.1 . . ?
H13A C13 H13B 107.8 . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?

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
C6 C7 C8 C10 -166.39(13) . . . . ?
C4 C7 C8 C10 16.50(18) . . . . ?
C6 C7 C8 C9 -29.87(19) . . . . ?
C4 C7 C8 C9 153.02(13) . . . . ?
C6 C7 C8 S1 61.02(16) . . . . ?
C4 C7 C8 S1 -116.09(13) . . . . ?
O3 S1 C8 C10 -136.68(10) . . . . ?
O2 S1 C8 C10 2.36(12) . . . . ?
N2 S1 C8 C10 112.14(11) . . . . ?
C9 S1 C8 C10 110.38(13) . . . . ?
O3 S1 C8 C7 -3.19(13) . . . . ?
O2 S1 C8 C7 135.85(10) . . . . ?
N2 S1 C8 C7 -114.36(11) . . . . ?
C9 S1 C8 C7 -116.13(13) . . . . ?
O3 S1 C8 C9 112.94(8) . . . . ?
O2 S1 C8 C9 -108.02(8) . . . . ?
N2 S1 C8 C9 1.76(8) . . . . ?
O3 S1 N2 C9 -113.03(9) . . . . ?
O2 S1 N2 C9 110.08(9) . . . . ?
C8 S1 N2 C9 -2.00(9) . . . . ?
C13 N1 C9 N2 178.24(13) . . . . ?
C11 N1 C9 N2 -2.9(2) . . . . ?
C13 N1 C9 C8 -1.5(2) . . . . ?
C11 N1 C9 C8 177.42(13) . . . . ?
S1 N2 C9 N1 -177.22(13) . . . . ?
S1 N2 C9 C8 2.55(11) . . . . ?
C10 C8 C9 N1 68.20(18) . . . . ?
C7 C8 C9 N1 -68.75(18) . . . . ?
S1 C8 C9 N1 177.51(14) . . . . ?
C10 C8 C9 N2 -111.57(13) . . . . ?
C7 C8 C9 N2 111.48(14) . . . . ?
S1 C8 C9 N2 -2.26(10) . . . . ?
C10 C8 C9 S1 -109.31(12) . . . . ?
C7 C8 C9 S1 113.74(12) . . . . ?
C1 O1 C2 C5 -7.1(2) . . . . ?
C1 O1 C2 C3 172.47(13) . . . . ?
O1 C2 C3 C4 -175.22(13) . . . . ?
C5 C2 C3 C4 4.3(2) . . . . ?
C2 C3 C4 C7 -1.5(2) . . . . ?
C6 C7 C4 C3 -2.2(2) . . . . ?
C8 C7 C4 C3 174.93(13) . . . . ?
O1 C2 C5 C6 176.05(13) . . . . ?
C3 C2 C5 C6 -3.5(2) . . . . ?
C2 C5 C6 C7 -0.2(2) . . . . ?
C4 C7 C6 C5 3.1(2) . . . . ?
C8 C7 C6 C5 -174.09(13) . . . . ?
C9 N1 C11 C12 -85.29(16) . . . . ?
C13 N1 C11 C12 93.65(15) . . . . ?
C9 N1 C13 C14 -100.86(15) . . . . ?
C11 N1 C13 C14 80.23(16) . . . . ?

_refine_diff_density_max         0.349
_refine_diff_density_min         -0.342
_refine_diff_density_rms         0.055



####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_A_140
_database_code_depnum_ccdc_archive 'CCDC 1821387'
_audit_update_record             
;
2018-02-01 deposited with the CCDC.
2018-11-08 downloaded from the CCDC.
;
_audit_creation_date             2016-04-18
_audit_creation_method           SHELXL-2016/6
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.5
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
#------------------ CHEMICAL INFORMATION ------------------------------------# 
_chemical_name_systematic        
;
'3-Diethylamino-4-(4-methoxyphenyl)-1,1-dioxo-4H-1λ⁶
,2-thiazete-4-carbonitrile'
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H17 N3 O3 S'
_chemical_formula_sum            'C14 H17 N3 O3 S'
_chemical_formula_weight         307.36

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.55700(10)
_cell_length_b                   13.2608(2)
_cell_length_c                   13.0750(2)
_cell_angle_alpha                90
_cell_angle_beta                 95.0428(7)
_cell_angle_gamma                90
_cell_volume                     1477.91(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    140(2)
_cell_measurement_reflns_used    7271
_cell_measurement_theta_min      2.1915
_cell_measurement_theta_max      27.503

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.381
_exptl_crystal_F_000             648
_exptl_transmission_factor_min   0.9064
_exptl_transmission_factor_max   0.9391
_exptl_crystal_size_max          0.275
_exptl_crystal_size_mid          0.179
_exptl_crystal_size_min          0.125
_exptl_absorpt_coefficient_mu    0.233
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.9064
_exptl_absorpt_correction_T_max  0.9391
_exptl_absorpt_process_details   'SADABS-2007/4, Bruker'
_diffrn_ambient_temperature      140(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed X-ray tube'
_diffrn_measurement_device_type  'Bruker AXS Smart APEX'
_diffrn_measurement_method       ω-scan
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22262
_diffrn_reflns_av_unetI/netI     0.0189
_diffrn_reflns_av_R_equivalents  0.0280
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.192
_diffrn_reflns_theta_max         27.553
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3403
_reflns_number_gt                2897
_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       'Saint+(Bruker, 2007/4)'
_computing_cell_refinement       'Saint+(Bruker, 2007/4)'
_computing_data_reduction        'Saint+(Bruker, 2007/4)'
_computing_structure_solution    'SHELXS-2016 (Sheldrick, 2016)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.0521P)²+0.7321P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   direct
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3403
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0434
_refine_ls_R_factor_gt           0.0359
_refine_ls_wR_factor_ref         0.0992
_refine_ls_wR_factor_gt          0.0932
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_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 0.16803(4) 0.56083(3) 0.71076(3) 0.02115(11) Uani 1 1 d . . . . .
N1 N 0.46976(14) 0.68274(9) 0.59428(9) 0.0201(3) Uani 1 1 d . . . . .
C10 C 0.17444(16) 0.55647(10) 0.49753(11) 0.0202(3) Uani 1 1 d . . . . .
C7 C 0.08383(16) 0.72026(10) 0.56460(11) 0.0187(3) Uani 1 1 d . . . . .
C8 C 0.18356(16) 0.62713(10) 0.58366(11) 0.0189(3) Uani 1 1 d . . . . .
O1 O -0.22653(13) 0.95964(8) 0.52737(9) 0.0307(3) Uani 1 1 d . . . . .
O3 O 0.06778(13) 0.61225(8) 0.77552(8) 0.0282(3) Uani 1 1 d . . . . .
N2 N 0.35258(14) 0.59879(10) 0.72745(9) 0.0227(3) Uani 1 1 d . . . . .
C9 C 0.35083(16) 0.63983(10) 0.63489(11) 0.0194(3) Uani 1 1 d . . . . .
C2 C -0.11614(17) 0.88566(11) 0.54203(11) 0.0222(3) Uani 1 1 d . . . . .
N3 N 0.17000(16) 0.50041(10) 0.43096(11) 0.0284(3) Uani 1 1 d . . . . .
C3 C -0.13334(17) 0.80567(11) 0.47285(11) 0.0216(3) Uani 1 1 d . . . . .
H3 H -0.2132(15) 0.80793(12) 0.4172(11) 0.026 Uiso 1 1 calc R U . . .
C4 C -0.03481(16) 0.72295(11) 0.48468(11) 0.0198(3) Uani 1 1 d . . . . .
H4 H -0.0480(3) 0.6685(11) 0.4387(9) 0.024 Uiso 1 1 calc R U . . .
C5 C 0.00626(17) 0.88583(11) 0.61933(12) 0.0236(3) Uani 1 1 d . . . . .
H5 H 0.0215(4) 0.9410(11) 0.6636(9) 0.028 Uiso 1 1 calc R U . . .
C6 C 0.10574(17) 0.80290(11) 0.62989(11) 0.0219(3) Uani 1 1 d . . . . .
H6 H 0.1879(16) 0.80265(11) 0.6812(10) 0.026 Uiso 1 1 calc R U . . .
O2 O 0.15636(13) 0.45309(8) 0.70240(8) 0.0274(3) Uani 1 1 d . . . . .
C11 C 0.62097(17) 0.69168(12) 0.65660(12) 0.0251(3) Uani 1 1 d . . . . .
H11A H 0.7049(11) 0.69423(12) 0.6118(6) 0.030 Uiso 1 1 calc R U . . .
H11B H 0.6369(3) 0.6328(8) 0.6999(6) 0.030 Uiso 1 1 calc R U . . .
C14 C 0.52645(19) 0.65311(13) 0.41350(12) 0.0296(3) Uani 1 1 d . . . . .
H14A H 0.5159(2) 0.6830(4) 0.3460(8) 0.044 Uiso 1 1 calc R U . . .
H14B H 0.6359(13) 0.64178(19) 0.4344(3) 0.044 Uiso 1 1 calc R U . . .
H14C H 0.4711(6) 0.5897(7) 0.41193(12) 0.044 Uiso 1 1 calc R U . . .
C13 C 0.45767(17) 0.72375(12) 0.48945(11) 0.0239(3) Uani 1 1 d . . . . .
H13A H 0.5127(7) 0.7883(8) 0.48965(11) 0.029 Uiso 1 1 calc R U . . .
H13B H 0.3474(14) 0.7361(2) 0.4671(3) 0.029 Uiso 1 1 calc R U . . .
C1 C -0.2256(2) 1.03728(13) 0.60365(15) 0.0353(4) Uani 1 1 d . . . . .
H1A H -0.3097(11) 1.0855(6) 0.5846(3) 0.053 Uiso 1 1 calc R U . . .
H1B H -0.2420(3) 1.0072(4) 0.6702(8) 0.053 Uiso 1 1 calc R U . . .
H1C H -0.1244(13) 1.0722(5) 0.60827(16) 0.053 Uiso 1 1 calc R U . . .
C12 C 0.6265(2) 0.78510(15) 0.72280(15) 0.0396(4) Uani 1 1 d . . . . .
H12A H 0.7287(13) 0.78891(16) 0.7634(5) 0.059 Uiso 1 1 calc R U . . .
H12B H 0.6122(3) 0.8451(8) 0.6789(6) 0.059 Uiso 1 1 calc R U . . .
H12C H 0.5424(11) 0.78210(15) 0.7693(6) 0.059 Uiso 1 1 calc R U . . .


_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 O3 1.4302(11) . ?
S1 O2 1.4357(11) . ?
S1 N2 1.6536(13) . ?
S1 C8 1.8950(14) . ?
S1 C9 2.1912(15) . ?
N1 C9 1.3177(18) . ?
N1 C13 1.4697(18) . ?
N1 C11 1.4720(18) . ?
C10 N3 1.1428(19) . ?
C10 C8 1.462(2) . ?
C7 C4 1.3919(19) . ?
C7 C6 1.3917(19) . ?
C7 C8 1.5094(19) . ?
C8 C9 1.5353(19) . ?
O1 C2 1.3636(18) . ?
O1 C1 1.433(2) . ?
N2 C9 1.3259(19) . ?
C2 C5 1.390(2) . ?
C2 C3 1.393(2) . ?
C3 C4 1.384(2) . ?
C3 H3 0.954(18) . ?
C4 H4 0.940(18) . ?
C5 C6 1.390(2) . ?
C5 H5 0.935(18) . ?
C6 H6 0.928(18) . ?
C11 C12 1.510(2) . ?
C11 H11A 0.967(13) . ?
C11 H11B 0.967(13) . ?
C14 C13 1.521(2) . ?
C14 H14A 0.964(11) . ?
C14 H14B 0.964(11) . ?
C14 H14C 0.964(11) . ?
C13 H13A 0.977(13) . ?
C13 H13B 0.977(13) . ?
C1 H1A 0.979(12) . ?
C1 H1B 0.979(12) . ?
C1 H1C 0.979(12) . ?
C12 H12A 0.983(12) . ?
C12 H12B 0.983(12) . ?
C12 H12C 0.983(12) . ?

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
O3 S1 O2 118.57(7) . . ?
O3 S1 N2 113.10(7) . . ?
O2 S1 N2 111.85(7) . . ?
O3 S1 C8 112.95(6) . . ?
O2 S1 C8 113.87(6) . . ?
N2 S1 C8 80.49(6) . . ?
O3 S1 C9 121.96(6) . . ?
O2 S1 C9 119.27(6) . . ?
N2 S1 C9 37.13(6) . . ?
C8 S1 C9 43.39(5) . . ?
C9 N1 C13 122.83(12) . . ?
C9 N1 C11 118.95(12) . . ?
C13 N1 C11 118.21(12) . . ?
N3 C10 C8 178.66(16) . . ?
C4 C7 C6 119.37(13) . . ?
C4 C7 C8 120.62(12) . . ?
C6 C7 C8 119.95(13) . . ?
C10 C8 C7 113.96(12) . . ?
C10 C8 C9 113.02(11) . . ?
C7 C8 C9 118.30(12) . . ?
C10 C8 S1 112.03(10) . . ?
C7 C8 S1 116.24(10) . . ?
C9 C8 S1 78.63(8) . . ?
C2 O1 C1 117.24(13) . . ?
C9 N2 S1 94.04(9) . . ?
N1 C9 N2 126.73(13) . . ?
N1 C9 C8 126.51(13) . . ?
N2 C9 C8 106.77(12) . . ?
N1 C9 S1 175.03(11) . . ?
N2 C9 S1 48.83(7) . . ?
C8 C9 S1 57.98(7) . . ?
O1 C2 C5 124.70(14) . . ?
O1 C2 C3 115.10(13) . . ?
C5 C2 C3 120.20(13) . . ?
C4 C3 C2 120.15(14) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C3 C4 C7 120.08(13) . . ?
C3 C4 H4 120.0 . . ?
C7 C4 H4 120.0 . . ?
C6 C5 C2 119.12(14) . . ?
C6 C5 H5 120.4 . . ?
C2 C5 H5 120.4 . . ?
C5 C6 C7 120.91(14) . . ?
C5 C6 H6 119.5 . . ?
C7 C6 H6 119.5 . . ?
N1 C11 C12 111.43(13) . . ?
N1 C11 H11A 109.3 . . ?
C12 C11 H11A 109.3 . . ?
N1 C11 H11B 109.3 . . ?
C12 C11 H11B 109.3 . . ?
H11A C11 H11B 108.0 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N1 C13 C14 112.43(12) . . ?
N1 C13 H13A 109.1 . . ?
C14 C13 H13A 109.1 . . ?
N1 C13 H13B 109.1 . . ?
C14 C13 H13B 109.1 . . ?
H13A C13 H13B 107.9 . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?

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
C4 C7 C8 C10 16.27(18) . . . . ?
C6 C7 C8 C10 -166.45(13) . . . . ?
C4 C7 C8 C9 152.77(13) . . . . ?
C6 C7 C8 C9 -29.95(19) . . . . ?
C4 C7 C8 S1 -116.32(13) . . . . ?
C6 C7 C8 S1 60.96(16) . . . . ?
O3 S1 C8 C10 -136.70(10) . . . . ?
O2 S1 C8 C10 2.35(12) . . . . ?
N2 S1 C8 C10 112.14(11) . . . . ?
C9 S1 C8 C10 110.42(12) . . . . ?
O3 S1 C8 C7 -3.23(13) . . . . ?
O2 S1 C8 C7 135.82(10) . . . . ?
N2 S1 C8 C7 -114.39(11) . . . . ?
C9 S1 C8 C7 -116.11(13) . . . . ?
O3 S1 C8 C9 112.88(8) . . . . ?
O2 S1 C8 C9 -108.07(8) . . . . ?
N2 S1 C8 C9 1.72(8) . . . . ?
O3 S1 N2 C9 -112.95(9) . . . . ?
O2 S1 N2 C9 110.07(9) . . . . ?
C8 S1 N2 C9 -1.95(9) . . . . ?
C13 N1 C9 N2 178.17(14) . . . . ?
C11 N1 C9 N2 -2.8(2) . . . . ?
C13 N1 C9 C8 -1.4(2) . . . . ?
C11 N1 C9 C8 177.66(13) . . . . ?
S1 N2 C9 N1 -177.15(13) . . . . ?
S1 N2 C9 C8 2.48(11) . . . . ?
C10 C8 C9 N1 68.14(18) . . . . ?
C7 C8 C9 N1 -68.75(18) . . . . ?
S1 C8 C9 N1 177.43(14) . . . . ?
C10 C8 C9 N2 -111.49(13) . . . . ?
C7 C8 C9 N2 111.62(14) . . . . ?
S1 C8 C9 N2 -2.20(10) . . . . ?
C10 C8 C9 S1 -109.29(12) . . . . ?
C7 C8 C9 S1 113.83(12) . . . . ?
C1 O1 C2 C5 -7.0(2) . . . . ?
C1 O1 C2 C3 172.58(13) . . . . ?
O1 C2 C3 C4 -175.44(13) . . . . ?
C5 C2 C3 C4 4.2(2) . . . . ?
C2 C3 C4 C7 -1.3(2) . . . . ?
C6 C7 C4 C3 -2.3(2) . . . . ?
C8 C7 C4 C3 174.97(13) . . . . ?
O1 C2 C5 C6 176.17(14) . . . . ?
C3 C2 C5 C6 -3.4(2) . . . . ?
C2 C5 C6 C7 -0.2(2) . . . . ?
C4 C7 C6 C5 3.1(2) . . . . ?
C8 C7 C6 C5 -174.23(13) . . . . ?
C9 N1 C11 C12 -85.28(17) . . . . ?
C13 N1 C11 C12 93.81(16) . . . . ?
C9 N1 C13 C14 -100.93(16) . . . . ?
C11 N1 C13 C14 80.03(16) . . . . ?

_refine_diff_density_max         0.345
_refine_diff_density_min         -0.314
_refine_diff_density_rms         0.051



####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_A_180
_database_code_depnum_ccdc_archive 'CCDC 1821384'
_audit_update_record             
;
2018-02-01 deposited with the CCDC.
2018-11-08 downloaded from the CCDC.
;
_audit_creation_date             2016-04-18
_audit_creation_method           SHELXL-2016/6
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.5
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
#------------------ CHEMICAL INFORMATION ------------------------------------# 
_chemical_name_systematic        
;
'3-Diethylamino-4-(4-methoxyphenyl)-1,1-dioxo-4H-1λ⁶
,2-thiazete-4-carbonitrile'
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H17 N3 O3 S'
_chemical_formula_sum            'C14 H17 N3 O3 S'
_chemical_formula_weight         307.36

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.57320(10)
_cell_length_b                   13.2867(2)
_cell_length_c                   13.1056(2)
_cell_angle_alpha                90
_cell_angle_beta                 94.9773(7)
_cell_angle_gamma                90
_cell_volume                     1487.22(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    6727
_cell_measurement_theta_min      2.187
_cell_measurement_theta_max      27.511

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.373
_exptl_crystal_F_000             648
_exptl_transmission_factor_min   0.9043
_exptl_transmission_factor_max   0.9391
_exptl_crystal_size_max          0.275
_exptl_crystal_size_mid          0.179
_exptl_crystal_size_min          0.125
_exptl_absorpt_coefficient_mu    0.231
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.9043
_exptl_absorpt_correction_T_max  0.9391
_exptl_absorpt_process_details   'SADABS-2007/4, Bruker'
_diffrn_ambient_temperature      180(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed X-ray tube'
_diffrn_measurement_device_type  'Bruker AXS Smart APEX'
_diffrn_measurement_method       ω-scan
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22412
_diffrn_reflns_av_unetI/netI     0.0192
_diffrn_reflns_av_R_equivalents  0.0280
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.187
_diffrn_reflns_theta_max         27.544
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3429
_reflns_number_gt                2871
_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       'Saint+(Bruker, 2007/4)'
_computing_cell_refinement       'Saint+(Bruker, 2007/4)'
_computing_data_reduction        'Saint+(Bruker, 2007/4)'
_computing_structure_solution    'SHELXS-2016 (Sheldrick, 2016)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.0543P)²+0.6799P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   direct
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3429
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0455
_refine_ls_R_factor_gt           0.0369
_refine_ls_wR_factor_ref         0.1028
_refine_ls_wR_factor_gt          0.0961
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_restrained_S_all      1.009
_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 0.16810(4) 0.56063(3) 0.71059(3) 0.02620(12) Uani 1 1 d . . . . .
N1 N 0.46877(14) 0.68289(9) 0.59457(9) 0.0250(3) Uani 1 1 d . . . . .
C10 C 0.17443(17) 0.55669(11) 0.49787(11) 0.0250(3) Uani 1 1 d . . . . .
C7 C 0.08378(16) 0.71996(11) 0.56516(11) 0.0229(3) Uani 1 1 d . . . . .
C8 C 0.18348(17) 0.62721(11) 0.58395(11) 0.0232(3) Uani 1 1 d . . . . .
O1 O -0.22507(14) 0.95927(9) 0.52787(10) 0.0384(3) Uani 1 1 d . . . . .
O3 O 0.06816(14) 0.61154(9) 0.77531(9) 0.0351(3) Uani 1 1 d . . . . .
N2 N 0.35207(15) 0.59845(10) 0.72717(10) 0.0280(3) Uani 1 1 d . . . . .
C9 C 0.35020(17) 0.63980(11) 0.63490(11) 0.0236(3) Uani 1 1 d . . . . .
C2 C -0.11549(18) 0.88528(11) 0.54268(12) 0.0271(3) Uani 1 1 d . . . . .
N3 N 0.17013(17) 0.50088(10) 0.43146(11) 0.0349(3) Uani 1 1 d . . . . .
C3 C -0.13228(17) 0.80548(11) 0.47342(12) 0.0263(3) Uani 1 1 d . . . . .
H3 H -0.2122(16) 0.80785(12) 0.4173(11) 0.032 Uiso 1 1 calc R U . . .
C4 C -0.03419(17) 0.72306(11) 0.48542(11) 0.0239(3) Uani 1 1 d . . . . .
H4 H -0.0471(3) 0.6695(11) 0.4400(9) 0.029 Uiso 1 1 calc R U . . .
C5 C 0.00608(18) 0.88501(12) 0.61986(12) 0.0290(3) Uani 1 1 d . . . . .
H5 H 0.0213(4) 0.9402(11) 0.6644(9) 0.035 Uiso 1 1 calc R U . . .
C6 C 0.10499(18) 0.80225(11) 0.63050(12) 0.0269(3) Uani 1 1 d . . . . .
H6 H 0.1868(17) 0.80181(11) 0.6822(11) 0.032 Uiso 1 1 calc R U . . .
O2 O 0.15660(14) 0.45321(8) 0.70195(9) 0.0338(3) Uani 1 1 d . . . . .
C11 C 0.61977(17) 0.69145(12) 0.65659(12) 0.0303(3) Uani 1 1 d . . . . .
H11A H 0.7037(11) 0.69432(13) 0.6116(6) 0.036 Uiso 1 1 calc R U . . .
H11B H 0.6358(3) 0.6321(8) 0.6994(6) 0.036 Uiso 1 1 calc R U . . .
C14 C 0.5255(2) 0.65347(14) 0.41425(13) 0.0366(4) Uani 1 1 d . . . . .
H14A H 0.5152(2) 0.6838(4) 0.3464(8) 0.055 Uiso 1 1 calc R U . . .
H14B H 0.6358(13) 0.6417(2) 0.4352(3) 0.055 Uiso 1 1 calc R U . . .
H14C H 0.4693(7) 0.5897(8) 0.41249(13) 0.055 Uiso 1 1 calc R U . . .
C13 C 0.45731(18) 0.72385(12) 0.49014(12) 0.0294(3) Uani 1 1 d . . . . .
H13A H 0.5125(7) 0.7880(9) 0.49046(12) 0.035 Uiso 1 1 calc R U . . .
H13B H 0.3477(14) 0.7365(2) 0.4679(3) 0.035 Uiso 1 1 calc R U . . .
C1 C -0.2248(2) 1.03671(14) 0.60383(16) 0.0446(5) Uani 1 1 d . . . . .
H1A H -0.3089(11) 1.0851(7) 0.5844(3) 0.067 Uiso 1 1 calc R U . . .
H1B H -0.2422(3) 1.0066(4) 0.6704(9) 0.067 Uiso 1 1 calc R U . . .
H1C H -0.1234(14) 1.0716(5) 0.60887(18) 0.067 Uiso 1 1 calc R U . . .
C12 C 0.6259(2) 0.78391(17) 0.72333(16) 0.0498(5) Uani 1 1 d . . . . .
H12A H 0.7260(13) 0.78721(18) 0.7628(6) 0.075 Uiso 1 1 calc R U . . .
H12B H 0.6119(3) 0.8430(8) 0.6809(6) 0.075 Uiso 1 1 calc R U . . .
H12C H 0.5438(11) 0.78066(17) 0.7690(6) 0.075 Uiso 1 1 calc R U . . .


_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 O3 1.4273(12) . ?
S1 O2 1.4344(12) . ?
S1 N2 1.6516(13) . ?
S1 C8 1.8954(15) . ?
S1 C9 2.1902(15) . ?
N1 C9 1.3166(19) . ?
N1 C13 1.4682(19) . ?
N1 C11 1.4721(19) . ?
C10 N3 1.142(2) . ?
C10 C8 1.463(2) . ?
C7 C4 1.390(2) . ?
C7 C6 1.391(2) . ?
C7 C8 1.508(2) . ?
C8 C9 1.533(2) . ?
O1 C2 1.3620(18) . ?
O1 C1 1.431(2) . ?
N2 C9 1.3271(19) . ?
C2 C5 1.388(2) . ?
C2 C3 1.395(2) . ?
C3 C4 1.381(2) . ?
C3 H3 0.961(18) . ?
C4 H4 0.928(18) . ?
C5 C6 1.388(2) . ?
C5 H5 0.939(19) . ?
C6 H6 0.931(19) . ?
C11 C12 1.506(2) . ?
C11 H11A 0.970(13) . ?
C11 H11B 0.970(13) . ?
C14 C13 1.519(2) . ?
C14 H14A 0.974(11) . ?
C14 H14B 0.974(11) . ?
C14 H14C 0.974(11) . ?
C13 H13A 0.974(13) . ?
C13 H13B 0.974(13) . ?
C1 H1A 0.983(13) . ?
C1 H1B 0.983(13) . ?
C1 H1C 0.983(13) . ?
C12 H12A 0.964(13) . ?
C12 H12B 0.964(13) . ?
C12 H12C 0.964(13) . ?

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
O3 S1 O2 118.54(7) . . ?
O3 S1 N2 113.16(7) . . ?
O2 S1 N2 111.80(7) . . ?
O3 S1 C8 112.96(7) . . ?
O2 S1 C8 113.88(7) . . ?
N2 S1 C8 80.50(6) . . ?
O3 S1 C9 121.99(6) . . ?
O2 S1 C9 119.27(6) . . ?
N2 S1 C9 37.19(6) . . ?
C8 S1 C9 43.34(6) . . ?
C9 N1 C13 122.94(13) . . ?
C9 N1 C11 118.98(12) . . ?
C13 N1 C11 118.08(12) . . ?
N3 C10 C8 178.65(16) . . ?
C4 C7 C6 119.15(13) . . ?
C4 C7 C8 120.80(13) . . ?
C6 C7 C8 119.99(13) . . ?
C10 C8 C7 113.95(12) . . ?
C10 C8 C9 112.99(12) . . ?
C7 C8 C9 118.41(12) . . ?
C10 C8 S1 111.91(10) . . ?
C7 C8 S1 116.30(10) . . ?
C9 C8 S1 78.62(8) . . ?
C2 O1 C1 117.42(14) . . ?
C9 N2 S1 94.03(10) . . ?
N1 C9 N2 126.66(14) . . ?
N1 C9 C8 126.56(13) . . ?
N2 C9 C8 106.78(12) . . ?
N1 C9 S1 174.97(11) . . ?
N2 C9 S1 48.78(7) . . ?
C8 C9 S1 58.04(7) . . ?
O1 C2 C5 124.80(14) . . ?
O1 C2 C3 115.15(14) . . ?
C5 C2 C3 120.05(14) . . ?
C4 C3 C2 120.07(14) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C4 C7 120.33(14) . . ?
C3 C4 H4 119.8 . . ?
C7 C4 H4 119.8 . . ?
C6 C5 C2 119.25(14) . . ?
C6 C5 H5 120.4 . . ?
C2 C5 H5 120.4 . . ?
C5 C6 C7 120.98(14) . . ?
C5 C6 H6 119.5 . . ?
C7 C6 H6 119.5 . . ?
N1 C11 C12 111.62(14) . . ?
N1 C11 H11A 109.3 . . ?
C12 C11 H11A 109.3 . . ?
N1 C11 H11B 109.3 . . ?
C12 C11 H11B 109.3 . . ?
H11A C11 H11B 108.0 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N1 C13 C14 112.57(13) . . ?
N1 C13 H13A 109.1 . . ?
C14 C13 H13A 109.1 . . ?
N1 C13 H13B 109.1 . . ?
C14 C13 H13B 109.1 . . ?
H13A C13 H13B 107.8 . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?

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
C4 C7 C8 C10 15.94(19) . . . . ?
C6 C7 C8 C10 -166.71(13) . . . . ?
C4 C7 C8 C9 152.51(13) . . . . ?
C6 C7 C8 C9 -30.1(2) . . . . ?
C4 C7 C8 S1 -116.51(13) . . . . ?
C6 C7 C8 S1 60.83(16) . . . . ?
O3 S1 C8 C10 -136.69(10) . . . . ?
O2 S1 C8 C10 2.34(13) . . . . ?
N2 S1 C8 C10 112.08(11) . . . . ?
C9 S1 C8 C10 110.40(13) . . . . ?
O3 S1 C8 C7 -3.31(13) . . . . ?
O2 S1 C8 C7 135.72(11) . . . . ?
N2 S1 C8 C7 -114.54(12) . . . . ?
C9 S1 C8 C7 -116.22(14) . . . . ?
O3 S1 C8 C9 112.92(9) . . . . ?
O2 S1 C8 C9 -108.06(9) . . . . ?
N2 S1 C8 C9 1.68(8) . . . . ?
O3 S1 N2 C9 -112.92(10) . . . . ?
O2 S1 N2 C9 110.12(10) . . . . ?
C8 S1 N2 C9 -1.91(9) . . . . ?
C13 N1 C9 N2 177.88(14) . . . . ?
C11 N1 C9 N2 -2.6(2) . . . . ?
C13 N1 C9 C8 -1.7(2) . . . . ?
C11 N1 C9 C8 177.80(13) . . . . ?
S1 N2 C9 N1 -177.25(13) . . . . ?
S1 N2 C9 C8 2.43(12) . . . . ?
C10 C8 C9 N1 68.37(18) . . . . ?
C7 C8 C9 N1 -68.59(19) . . . . ?
S1 C8 C9 N1 177.52(14) . . . . ?
C10 C8 C9 N2 -111.31(14) . . . . ?
C7 C8 C9 N2 111.73(14) . . . . ?
S1 C8 C9 N2 -2.16(10) . . . . ?
C10 C8 C9 S1 -109.15(12) . . . . ?
C7 C8 C9 S1 113.89(13) . . . . ?
C1 O1 C2 C5 -7.1(2) . . . . ?
C1 O1 C2 C3 172.62(14) . . . . ?
O1 C2 C3 C4 -175.59(13) . . . . ?
C5 C2 C3 C4 4.2(2) . . . . ?
C2 C3 C4 C7 -1.3(2) . . . . ?
C6 C7 C4 C3 -2.1(2) . . . . ?
C8 C7 C4 C3 175.25(13) . . . . ?
O1 C2 C5 C6 176.28(14) . . . . ?
C3 C2 C5 C6 -3.4(2) . . . . ?
C2 C5 C6 C7 -0.1(2) . . . . ?
C4 C7 C6 C5 2.8(2) . . . . ?
C8 C7 C6 C5 -174.55(13) . . . . ?
C9 N1 C11 C12 -85.24(18) . . . . ?
C13 N1 C11 C12 94.32(17) . . . . ?
C9 N1 C13 C14 -100.48(17) . . . . ?
C11 N1 C13 C14 79.99(17) . . . . ?

_refine_diff_density_max         0.327
_refine_diff_density_min         -0.302
_refine_diff_density_rms         0.048



####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_A_120
_database_code_depnum_ccdc_archive 'CCDC 1821386'
_audit_update_record             
;
2018-02-01 deposited with the CCDC.
2018-11-08 downloaded from the CCDC.
;
_audit_creation_date             2016-04-18
_audit_creation_method           SHELXL-2016/6
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.5
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
#------------------ CHEMICAL INFORMATION ------------------------------------# _chemical_name_systematic         
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H17 N3 O3 S'
_chemical_formula_sum            'C14 H17 N3 O3 S'
_chemical_formula_weight         307.36

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.55060(10)
_cell_length_b                   13.2506(2)
_cell_length_c                   13.0615(2)
_cell_angle_alpha                90
_cell_angle_beta                 95.0620(7)
_cell_angle_gamma                90
_cell_volume                     1474.10(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    7488
_cell_measurement_theta_min      2.194
_cell_measurement_theta_max      27.527

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.385
_exptl_crystal_F_000             648
_exptl_transmission_factor_min   0.8996
_exptl_transmission_factor_max   0.9391
_exptl_crystal_size_max          0.275
_exptl_crystal_size_mid          0.179
_exptl_crystal_size_min          0.125
_exptl_absorpt_coefficient_mu    0.233
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.8996
_exptl_absorpt_correction_T_max  0.9391
_exptl_absorpt_process_details   'SADABS-2007/4, Bruker'
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed X-ray tube'
_diffrn_measurement_device_type  'Bruker AXS Smart APEX'
_diffrn_measurement_method       ω-scan
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22149
_diffrn_reflns_av_unetI/netI     0.0186
_diffrn_reflns_av_R_equivalents  0.0275
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.194
_diffrn_reflns_theta_max         27.555
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3393
_reflns_number_gt                2918
_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       'Saint+(Bruker, 2007/4)'
_computing_cell_refinement       'Saint+(Bruker, 2007/4)'
_computing_data_reduction        'Saint+(Bruker, 2007/4)'
_computing_structure_solution    'SHELXS-2016 (Sheldrick, 2016)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.0544P)²+0.7056P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   direct
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3393
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0433
_refine_ls_R_factor_gt           0.0360
_refine_ls_wR_factor_ref         0.1007
_refine_ls_wR_factor_gt          0.0942
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_restrained_S_all      1.044
_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 0.16796(4) 0.56093(3) 0.71086(3) 0.01887(11) Uani 1 1 d . . . . .
N1 N 0.46994(14) 0.68276(9) 0.59418(9) 0.0180(3) Uani 1 1 d . . . . .
C10 C 0.17453(16) 0.55636(11) 0.49731(11) 0.0187(3) Uani 1 1 d . . . . .
C7 C 0.08386(16) 0.72035(10) 0.56432(11) 0.0169(3) Uani 1 1 d . . . . .
C8 C 0.18351(16) 0.62721(10) 0.58359(11) 0.0169(3) Uani 1 1 d . . . . .
O1 O -0.22705(13) 0.95981(8) 0.52720(9) 0.0270(3) Uani 1 1 d . . . . .
O3 O 0.06763(13) 0.61246(8) 0.77562(8) 0.0251(2) Uani 1 1 d . . . . .
N2 N 0.35276(14) 0.59877(10) 0.72772(9) 0.0208(3) Uani 1 1 d . . . . .
C9 C 0.35086(16) 0.63985(10) 0.63473(11) 0.0177(3) Uani 1 1 d . . . . .
C2 C -0.11664(17) 0.88590(11) 0.54178(11) 0.0201(3) Uani 1 1 d . . . . .
N3 N 0.16975(16) 0.50013(10) 0.43058(11) 0.0257(3) Uani 1 1 d . . . . .
C3 C -0.13392(17) 0.80571(11) 0.47249(11) 0.0193(3) Uani 1 1 d . . . . .
H3 H -0.2151(15) 0.80797(12) 0.4159(11) 0.023 Uiso 1 1 calc R U . . .
C4 C -0.03523(16) 0.72290(11) 0.48450(11) 0.0180(3) Uani 1 1 d . . . . .
H4 H -0.0486(3) 0.6687(11) 0.4390(9) 0.022 Uiso 1 1 calc R U . . .
C5 C 0.00635(17) 0.88622(11) 0.61910(12) 0.0214(3) Uani 1 1 d . . . . .
H5 H 0.0217(4) 0.9414(11) 0.6632(9) 0.026 Uiso 1 1 calc R U . . .
C6 C 0.10594(17) 0.80326(11) 0.62967(11) 0.0197(3) Uani 1 1 d . . . . .
H6 H 0.1881(16) 0.80307(11) 0.6808(10) 0.024 Uiso 1 1 calc R U . . .
O2 O 0.15621(13) 0.45301(8) 0.70259(8) 0.0242(2) Uani 1 1 d . . . . .
C11 C 0.62143(17) 0.69197(12) 0.65659(11) 0.0221(3) Uani 1 1 d . . . . .
H11A H 0.7059(11) 0.69455(12) 0.6115(6) 0.027 Uiso 1 1 calc R U . . .
H11B H 0.6377(3) 0.6328(8) 0.7003(6) 0.027 Uiso 1 1 calc R U . . .
C14 C 0.52662(18) 0.65282(13) 0.41307(12) 0.0264(3) Uani 1 1 d . . . . .
H14A H 0.5159(2) 0.6830(4) 0.3449(8) 0.040 Uiso 1 1 calc R U . . .
H14B H 0.6372(13) 0.64140(19) 0.4342(3) 0.040 Uiso 1 1 calc R U . . .
H14C H 0.4707(6) 0.5888(7) 0.41158(12) 0.040 Uiso 1 1 calc R U . . .
C13 C 0.45782(17) 0.72364(11) 0.48904(11) 0.0210(3) Uani 1 1 d . . . . .
H13A H 0.5129(7) 0.7883(8) 0.48912(11) 0.025 Uiso 1 1 calc R U . . .
H13B H 0.3473(14) 0.7360(2) 0.4667(3) 0.025 Uiso 1 1 calc R U . . .
C1 C -0.2261(2) 1.03758(12) 0.60362(14) 0.0314(4) Uani 1 1 d . . . . .
H1A H -0.3103(10) 1.0858(6) 0.5846(3) 0.047 Uiso 1 1 calc R U . . .
H1B H -0.2424(3) 1.0075(4) 0.6702(8) 0.047 Uiso 1 1 calc R U . . .
H1C H -0.1250(12) 1.0725(5) 0.60820(16) 0.047 Uiso 1 1 calc R U . . .
C12 C 0.6267(2) 0.78556(15) 0.72260(14) 0.0354(4) Uani 1 1 d . . . . .
H12A H 0.7276(13) 0.78954(16) 0.7627(5) 0.053 Uiso 1 1 calc R U . . .
H12B H 0.6123(3) 0.8447(8) 0.6790(5) 0.053 Uiso 1 1 calc R U . . .
H12C H 0.5436(10) 0.78258(15) 0.7685(6) 0.053 Uiso 1 1 calc R U . . .


_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 O3 1.4303(11) . ?
S1 O2 1.4369(11) . ?
S1 N2 1.6539(13) . ?
S1 C8 1.8951(14) . ?
S1 C9 2.1914(15) . ?
N1 C9 1.3175(18) . ?
N1 C13 1.4714(18) . ?
N1 C11 1.4734(18) . ?
C10 N3 1.1447(19) . ?
C10 C8 1.464(2) . ?
C7 C4 1.392(2) . ?
C7 C6 1.3939(19) . ?
C7 C8 1.5082(19) . ?
C8 C9 1.5340(19) . ?
O1 C2 1.3620(17) . ?
O1 C1 1.434(2) . ?
N2 C9 1.3296(19) . ?
C2 C5 1.392(2) . ?
C2 C3 1.395(2) . ?
C3 C4 1.385(2) . ?
C3 H3 0.969(18) . ?
C4 H4 0.933(18) . ?
C5 C6 1.390(2) . ?
C5 H5 0.933(19) . ?
C6 H6 0.926(18) . ?
C11 C12 1.509(2) . ?
C11 H11A 0.973(13) . ?
C11 H11B 0.973(13) . ?
C14 C13 1.521(2) . ?
C14 H14A 0.973(11) . ?
C14 H14B 0.973(11) . ?
C14 H14C 0.973(11) . ?
C13 H13A 0.978(12) . ?
C13 H13B 0.978(12) . ?
C1 H1A 0.978(12) . ?
C1 H1B 0.978(12) . ?
C1 H1C 0.978(12) . ?
C12 H12A 0.970(12) . ?
C12 H12B 0.970(12) . ?
C12 H12C 0.970(12) . ?

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
O3 S1 O2 118.55(7) . . ?
O3 S1 N2 113.11(7) . . ?
O2 S1 N2 111.80(7) . . ?
O3 S1 C8 112.94(6) . . ?
O2 S1 C8 113.89(6) . . ?
N2 S1 C8 80.57(6) . . ?
O3 S1 C9 122.00(6) . . ?
O2 S1 C9 119.25(6) . . ?
N2 S1 C9 37.25(6) . . ?
C8 S1 C9 43.34(5) . . ?
C9 N1 C13 122.74(12) . . ?
C9 N1 C11 119.09(12) . . ?
C13 N1 C11 118.17(11) . . ?
N3 C10 C8 178.83(16) . . ?
C4 C7 C6 119.35(13) . . ?
C4 C7 C8 120.67(12) . . ?
C6 C7 C8 119.92(13) . . ?
C10 C8 C7 113.94(12) . . ?
C10 C8 C9 112.89(11) . . ?
C7 C8 C9 118.35(12) . . ?
C10 C8 S1 112.04(10) . . ?
C7 C8 S1 116.31(10) . . ?
C9 C8 S1 78.67(8) . . ?
C2 O1 C1 117.27(12) . . ?
C9 N2 S1 93.90(9) . . ?
N1 C9 N2 126.61(13) . . ?
N1 C9 C8 126.61(13) . . ?
N2 C9 C8 106.78(12) . . ?
N1 C9 S1 174.97(11) . . ?
N2 C9 S1 48.85(7) . . ?
C8 C9 S1 57.99(7) . . ?
O1 C2 C5 124.69(13) . . ?
O1 C2 C3 115.12(13) . . ?
C5 C2 C3 120.19(13) . . ?
C4 C3 C2 120.10(13) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C4 C7 120.15(13) . . ?
C3 C4 H4 119.9 . . ?
C7 C4 H4 119.9 . . ?
C6 C5 C2 119.12(13) . . ?
C6 C5 H5 120.4 . . ?
C2 C5 H5 120.4 . . ?
C5 C6 C7 120.92(14) . . ?
C5 C6 H6 119.5 . . ?
C7 C6 H6 119.5 . . ?
N1 C11 C12 111.39(13) . . ?
N1 C11 H11A 109.4 . . ?
C12 C11 H11A 109.4 . . ?
N1 C11 H11B 109.4 . . ?
C12 C11 H11B 109.4 . . ?
H11A C11 H11B 108.0 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N1 C13 C14 112.47(12) . . ?
N1 C13 H13A 109.1 . . ?
C14 C13 H13A 109.1 . . ?
N1 C13 H13B 109.1 . . ?
C14 C13 H13B 109.1 . . ?
H13A C13 H13B 107.8 . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?

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
C4 C7 C8 C10 16.59(18) . . . . ?
C6 C7 C8 C10 -166.36(13) . . . . ?
C4 C7 C8 C9 152.91(13) . . . . ?
C6 C7 C8 C9 -30.04(19) . . . . ?
C4 C7 C8 S1 -116.07(13) . . . . ?
C6 C7 C8 S1 60.98(16) . . . . ?
O3 S1 C8 C10 -136.76(10) . . . . ?
O2 S1 C8 C10 2.27(12) . . . . ?
N2 S1 C8 C10 112.04(11) . . . . ?
C9 S1 C8 C10 110.29(12) . . . . ?
O3 S1 C8 C7 -3.23(13) . . . . ?
O2 S1 C8 C7 135.80(10) . . . . ?
N2 S1 C8 C7 -114.44(11) . . . . ?
C9 S1 C8 C7 -116.18(13) . . . . ?
O3 S1 C8 C9 112.95(8) . . . . ?
O2 S1 C8 C9 -108.02(8) . . . . ?
N2 S1 C8 C9 1.75(8) . . . . ?
O3 S1 N2 C9 -113.00(9) . . . . ?
O2 S1 N2 C9 110.09(9) . . . . ?
C8 S1 N2 C9 -1.98(9) . . . . ?
C13 N1 C9 N2 178.12(13) . . . . ?
C11 N1 C9 N2 -2.8(2) . . . . ?
C13 N1 C9 C8 -1.6(2) . . . . ?
C11 N1 C9 C8 177.46(13) . . . . ?
S1 N2 C9 N1 -177.23(13) . . . . ?
S1 N2 C9 C8 2.52(11) . . . . ?
C10 C8 C9 N1 68.19(18) . . . . ?
C7 C8 C9 N1 -68.56(18) . . . . ?
S1 C8 C9 N1 177.51(14) . . . . ?
C10 C8 C9 N2 -111.56(13) . . . . ?
C7 C8 C9 N2 111.69(14) . . . . ?
S1 C8 C9 N2 -2.24(10) . . . . ?
C10 C8 C9 S1 -109.32(11) . . . . ?
C7 C8 C9 S1 113.93(12) . . . . ?
C1 O1 C2 C5 -7.1(2) . . . . ?
C1 O1 C2 C3 172.54(13) . . . . ?
O1 C2 C3 C4 -175.34(13) . . . . ?
C5 C2 C3 C4 4.4(2) . . . . ?
C2 C3 C4 C7 -1.5(2) . . . . ?
C6 C7 C4 C3 -2.2(2) . . . . ?
C8 C7 C4 C3 174.91(13) . . . . ?
O1 C2 C5 C6 176.14(14) . . . . ?
C3 C2 C5 C6 -3.5(2) . . . . ?
C2 C5 C6 C7 -0.1(2) . . . . ?
C4 C7 C6 C5 3.0(2) . . . . ?
C8 C7 C6 C5 -174.11(13) . . . . ?
C9 N1 C11 C12 -85.26(17) . . . . ?
C13 N1 C11 C12 93.82(16) . . . . ?
C9 N1 C13 C14 -100.86(16) . . . . ?
C11 N1 C13 C14 80.10(16) . . . . ?

_refine_diff_density_max         0.336
_refine_diff_density_min         -0.317
_refine_diff_density_rms         0.054



####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_A_260
_database_code_depnum_ccdc_archive 'CCDC 1821385'
_audit_update_record             
;
2018-02-01 deposited with the CCDC.
2018-11-08 downloaded from the CCDC.
;
_audit_creation_date             2016-04-18
_audit_creation_method           SHELXL-2016/6
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.5
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
#------------------ CHEMICAL INFORMATION ------------------------------------# 
_chemical_name_systematic        
;
'3-Diethylamino-4-(4-methoxyphenyl)-1,1-dioxo-4H-1λ⁶
,2-thiazete-4-carbonitrile'
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H17 N3 O3 S'
_chemical_formula_sum            'C14 H17 N3 O3 S'
_chemical_formula_weight         307.36

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.61220(10)
_cell_length_b                   13.3460(2)
_cell_length_c                   13.1742(2)
_cell_angle_alpha                90
_cell_angle_beta                 94.7854(8)
_cell_angle_gamma                90
_cell_volume                     1508.94(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    260(2)
_cell_measurement_reflns_used    5720
_cell_measurement_theta_min      2.714
_cell_measurement_theta_max      27.249

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_F_000             648
_exptl_transmission_factor_min   0.9179
_exptl_transmission_factor_max   0.9391
_exptl_crystal_size_max          0.275
_exptl_crystal_size_mid          0.179
_exptl_crystal_size_min          0.125
_exptl_absorpt_coefficient_mu    0.228
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.9179
_exptl_absorpt_correction_T_max  0.9391
_exptl_absorpt_process_details   'SADABS-2007/4, Bruker'
_diffrn_ambient_temperature      260(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed X-ray tube'
_diffrn_measurement_device_type  'Bruker AXS Smart APEX'
_diffrn_measurement_method       ω-scan
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22822
_diffrn_reflns_av_unetI/netI     0.0209
_diffrn_reflns_av_R_equivalents  0.0304
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.176
_diffrn_reflns_theta_max         27.561
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3489
_reflns_number_gt                2779
_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       'Saint+(Bruker, 2007/4)'
_computing_cell_refinement       'Saint+(Bruker, 2007/4)'
_computing_data_reduction        'Saint+(Bruker, 2007/4)'
_computing_structure_solution    'SHELXS-2016 (Sheldrick, 2016)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.0529P)²+0.5237P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   direct
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3489
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0518
_refine_ls_R_factor_gt           0.0391
_refine_ls_wR_factor_ref         0.1091
_refine_ls_wR_factor_gt          0.0998
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_restrained_S_all      1.017
_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 0.16796(5) 0.56001(3) 0.71014(3) 0.03853(14) Uani 1 1 d . . . . .
N1 N 0.46712(15) 0.68288(10) 0.59525(10) 0.0359(3) Uani 1 1 d . . . . .
C10 C 0.17490(18) 0.55742(12) 0.49881(13) 0.0359(3) Uani 1 1 d . . . . .
C7 C 0.08371(17) 0.71955(11) 0.56653(11) 0.0316(3) Uani 1 1 d . . . . .
C8 C 0.18329(18) 0.62710(11) 0.58465(12) 0.0328(3) Uani 1 1 d . . . . .
O1 O -0.22152(16) 0.95838(10) 0.52895(11) 0.0578(4) Uani 1 1 d . . . . .
O3 O 0.06849(15) 0.60997(10) 0.77500(10) 0.0516(3) Uani 1 1 d . . . . .
N2 N 0.35069(16) 0.59794(11) 0.72649(10) 0.0409(3) Uani 1 1 d . . . . .
C9 C 0.34904(18) 0.63959(11) 0.63517(12) 0.0338(3) Uani 1 1 d . . . . .
C2 C -0.1130(2) 0.88434(12) 0.54432(13) 0.0397(4) Uani 1 1 d . . . . .
N3 N 0.17103(19) 0.50213(11) 0.43278(13) 0.0512(4) Uani 1 1 d . . . . .
C3 C -0.12916(19) 0.80538(12) 0.47526(13) 0.0384(4) Uani 1 1 d . . . . .
H3 H -0.2065(16) 0.80814(14) 0.4202(12) 0.046 Uiso 1 1 calc R U . . .
C4 C -0.03249(18) 0.72313(12) 0.48703(12) 0.0343(3) Uani 1 1 d . . . . .
H4 H -0.0453(3) 0.6693(11) 0.4411(9) 0.041 Uiso 1 1 calc R U . . .
C5 C 0.0060(2) 0.88340(13) 0.62132(14) 0.0419(4) Uani 1 1 d . . . . .
H5 H 0.0203(4) 0.9372(12) 0.6654(10) 0.050 Uiso 1 1 calc R U . . .
C6 C 0.1040(2) 0.80093(12) 0.63186(13) 0.0384(4) Uani 1 1 d . . . . .
H6 H 0.1826(17) 0.80016(12) 0.6823(11) 0.046 Uiso 1 1 calc R U . . .
O2 O 0.15720(15) 0.45328(9) 0.70094(10) 0.0499(3) Uani 1 1 d . . . . .
C11 C 0.6175(2) 0.69075(14) 0.65676(14) 0.0448(4) Uani 1 1 d . . . . .
H11A H 0.7001(12) 0.69402(14) 0.6123(6) 0.054 Uiso 1 1 calc R U . . .
H11B H 0.6332(3) 0.6319(9) 0.6982(6) 0.054 Uiso 1 1 calc R U . . .
C14 C 0.5242(2) 0.65480(17) 0.41587(14) 0.0544(5) Uani 1 1 d . . . . .
H14A H 0.5141(3) 0.6853(4) 0.3492(9) 0.082 Uiso 1 1 calc R U . . .
H14B H 0.6330(14) 0.6432(2) 0.4364(3) 0.082 Uiso 1 1 calc R U . . .
H14C H 0.4688(7) 0.5918(8) 0.41374(15) 0.082 Uiso 1 1 calc R U . . .
C13 C 0.4562(2) 0.72398(14) 0.49164(13) 0.0424(4) Uani 1 1 d . . . . .
H13A H 0.5117(7) 0.7887(9) 0.49229(13) 0.051 Uiso 1 1 calc R U . . .
H13B H 0.3458(15) 0.7368(2) 0.4694(3) 0.051 Uiso 1 1 calc R U . . .
C1 C -0.2226(3) 1.03550(16) 0.6039(2) 0.0678(6) Uani 1 1 d . . . . .
H1A H -0.3071(13) 1.0845(8) 0.5835(3) 0.102 Uiso 1 1 calc R U . . .
H1B H -0.2417(4) 1.0053(5) 0.6711(10) 0.102 Uiso 1 1 calc R U . . .
H1C H -0.1199(15) 1.0706(6) 0.6096(2) 0.102 Uiso 1 1 calc R U . . .
C12 C 0.6242(3) 0.7816(2) 0.72393(19) 0.0735(7) Uani 1 1 d . . . . .
H12A H 0.7225(15) 0.7842(2) 0.7624(6) 0.110 Uiso 1 1 calc R U . . .
H12B H 0.6106(3) 0.8401(9) 0.6831(6) 0.110 Uiso 1 1 calc R U . . .
H12C H 0.5437(12) 0.7779(2) 0.7689(7) 0.110 Uiso 1 1 calc R U . . .


_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 O3 1.4250(13) . ?
S1 O2 1.4318(13) . ?
S1 N2 1.6501(14) . ?
S1 C8 1.8944(16) . ?
S1 C9 2.1892(16) . ?
N1 C9 1.317(2) . ?
N1 C13 1.467(2) . ?
N1 C11 1.473(2) . ?
C10 N3 1.139(2) . ?
C10 C8 1.461(2) . ?
C7 C6 1.388(2) . ?
C7 C4 1.388(2) . ?
C7 C8 1.510(2) . ?
C8 C9 1.533(2) . ?
O1 C2 1.363(2) . ?
O1 C1 1.427(3) . ?
N2 C9 1.324(2) . ?
C2 C5 1.381(3) . ?
C2 C3 1.392(2) . ?
C3 C4 1.379(2) . ?
C3 H3 0.944(19) . ?
C4 H4 0.940(18) . ?
C5 C6 1.387(2) . ?
C5 H5 0.93(2) . ?
C6 H6 0.91(2) . ?
C11 C12 1.499(3) . ?
C11 H11A 0.960(14) . ?
C11 H11B 0.960(13) . ?
C14 C13 1.513(3) . ?
C14 H14A 0.966(12) . ?
C14 H14B 0.966(12) . ?
C14 H14C 0.966(12) . ?
C13 H13A 0.987(13) . ?
C13 H13B 0.987(13) . ?
C1 H1A 0.999(15) . ?
C1 H1B 0.999(15) . ?
C1 H1C 0.999(15) . ?
C12 H12A 0.950(14) . ?
C12 H12B 0.950(14) . ?
C12 H12C 0.950(14) . ?

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
O3 S1 O2 118.58(8) . . ?
O3 S1 N2 113.12(8) . . ?
O2 S1 N2 111.75(8) . . ?
O3 S1 C8 113.03(7) . . ?
O2 S1 C8 113.90(7) . . ?
N2 S1 C8 80.43(7) . . ?
O3 S1 C9 122.00(7) . . ?
O2 S1 C9 119.21(7) . . ?
N2 S1 C9 37.11(6) . . ?
C8 S1 C9 43.35(6) . . ?
C9 N1 C13 122.97(14) . . ?
C9 N1 C11 118.98(14) . . ?
C13 N1 C11 118.05(13) . . ?
N3 C10 C8 178.59(18) . . ?
C6 C7 C4 119.12(14) . . ?
C6 C7 C8 120.06(14) . . ?
C4 C7 C8 120.78(14) . . ?
C10 C8 C7 114.01(13) . . ?
C10 C8 C9 112.91(13) . . ?
C7 C8 C9 118.41(13) . . ?
C10 C8 S1 111.84(11) . . ?
C7 C8 S1 116.37(10) . . ?
C9 C8 S1 78.62(9) . . ?
C2 O1 C1 117.65(16) . . ?
C9 N2 S1 94.15(11) . . ?
N1 C9 N2 126.65(15) . . ?
N1 C9 C8 126.62(14) . . ?
N2 C9 C8 106.73(13) . . ?
N1 C9 S1 174.90(12) . . ?
N2 C9 S1 48.74(8) . . ?
C8 C9 S1 58.03(8) . . ?
O1 C2 C5 124.99(16) . . ?
O1 C2 C3 114.95(16) . . ?
C5 C2 C3 120.06(15) . . ?
C4 C3 C2 120.19(16) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C3 C4 C7 120.20(15) . . ?
C3 C4 H4 119.9 . . ?
C7 C4 H4 119.9 . . ?
C2 C5 C6 119.27(16) . . ?
C2 C5 H5 120.4 . . ?
C6 C5 H5 120.4 . . ?
C5 C6 C7 121.00(16) . . ?
C5 C6 H6 119.5 . . ?
C7 C6 H6 119.5 . . ?
N1 C11 C12 111.78(16) . . ?
N1 C11 H11A 109.3 . . ?
C12 C11 H11A 109.3 . . ?
N1 C11 H11B 109.3 . . ?
C12 C11 H11B 109.3 . . ?
H11A C11 H11B 107.9 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N1 C13 C14 112.80(15) . . ?
N1 C13 H13A 109.0 . . ?
C14 C13 H13A 109.0 . . ?
N1 C13 H13B 109.0 . . ?
C14 C13 H13B 109.0 . . ?
H13A C13 H13B 107.8 . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?

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
C6 C7 C8 C10 -166.81(14) . . . . ?
C4 C7 C8 C10 15.5(2) . . . . ?
C6 C7 C8 C9 -30.3(2) . . . . ?
C4 C7 C8 C9 152.00(14) . . . . ?
C6 C7 C8 S1 60.71(18) . . . . ?
C4 C7 C8 S1 -116.99(14) . . . . ?
O3 S1 C8 C10 -136.82(12) . . . . ?
O2 S1 C8 C10 2.37(14) . . . . ?
N2 S1 C8 C10 112.02(12) . . . . ?
C9 S1 C8 C10 110.31(14) . . . . ?
O3 S1 C8 C7 -3.36(14) . . . . ?
O2 S1 C8 C7 135.83(12) . . . . ?
N2 S1 C8 C7 -114.52(12) . . . . ?
C9 S1 C8 C7 -116.23(15) . . . . ?
O3 S1 C8 C9 112.87(10) . . . . ?
O2 S1 C8 C9 -107.95(10) . . . . ?
N2 S1 C8 C9 1.71(9) . . . . ?
O3 S1 N2 C9 -113.00(11) . . . . ?
O2 S1 N2 C9 110.09(11) . . . . ?
C8 S1 N2 C9 -1.94(10) . . . . ?
C13 N1 C9 N2 177.68(16) . . . . ?
C11 N1 C9 N2 -2.3(2) . . . . ?
C13 N1 C9 C8 -1.9(2) . . . . ?
C11 N1 C9 C8 178.10(15) . . . . ?
S1 N2 C9 N1 -177.20(14) . . . . ?
S1 N2 C9 C8 2.47(13) . . . . ?
C10 C8 C9 N1 68.4(2) . . . . ?
C7 C8 C9 N1 -68.6(2) . . . . ?
S1 C8 C9 N1 177.48(15) . . . . ?
C10 C8 C9 N2 -111.27(15) . . . . ?
C7 C8 C9 N2 111.78(15) . . . . ?
S1 C8 C9 N2 -2.19(11) . . . . ?
C10 C8 C9 S1 -109.08(13) . . . . ?
C7 C8 C9 S1 113.96(13) . . . . ?
C1 O1 C2 C5 -6.9(3) . . . . ?
C1 O1 C2 C3 172.83(17) . . . . ?
O1 C2 C3 C4 -175.81(15) . . . . ?
C5 C2 C3 C4 4.0(2) . . . . ?
C2 C3 C4 C7 -1.4(2) . . . . ?
C6 C7 C4 C3 -1.9(2) . . . . ?
C8 C7 C4 C3 175.81(14) . . . . ?
O1 C2 C5 C6 176.62(16) . . . . ?
C3 C2 C5 C6 -3.1(3) . . . . ?
C2 C5 C6 C7 -0.2(3) . . . . ?
C4 C7 C6 C5 2.7(2) . . . . ?
C8 C7 C6 C5 -174.99(15) . . . . ?
C9 N1 C11 C12 -85.2(2) . . . . ?
C13 N1 C11 C12 94.82(19) . . . . ?
C9 N1 C13 C14 -100.35(18) . . . . ?
C11 N1 C13 C14 79.6(2) . . . . ?

_refine_diff_density_max         0.282
_refine_diff_density_min         -0.253
_refine_diff_density_rms         0.043



####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_A_220
_database_code_depnum_ccdc_archive 'CCDC 1821388'
_audit_update_record             
;
2018-02-01 deposited with the CCDC.
2018-11-08 downloaded from the CCDC.
;
_audit_creation_date             2016-04-18
_audit_creation_method           SHELXL-2016/6
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.5
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
#------------------ CHEMICAL INFORMATION ------------------------------------# 
_chemical_name_systematic        
;
'3-Diethylamino-4-(4-methoxyphenyl)-1,1-dioxo-4H-1λ⁶
,2-thiazete-4-carbonitrile'
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H17 N3 O3 S'
_chemical_formula_sum            'C14 H17 N3 O3 S'
_chemical_formula_weight         307.36

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.59120(10)
_cell_length_b                   13.3150(2)
_cell_length_c                   13.1382(2)
_cell_angle_alpha                90
_cell_angle_beta                 94.8947(7)
_cell_angle_gamma                90
_cell_volume                     1497.42(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    220(2)
_cell_measurement_reflns_used    6228
_cell_measurement_theta_min      2.1815
_cell_measurement_theta_max      27.434

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.363
_exptl_crystal_F_000             648
_exptl_transmission_factor_min   0.9049
_exptl_transmission_factor_max   0.9391
_exptl_crystal_size_max          0.275
_exptl_crystal_size_mid          0.179
_exptl_crystal_size_min          0.125
_exptl_absorpt_coefficient_mu    0.230
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.9049
_exptl_absorpt_correction_T_max  0.9391
_exptl_absorpt_process_details   'SADABS-2007/4, Bruker'
_diffrn_ambient_temperature      220(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed X-ray tube'
_diffrn_measurement_device_type  'Bruker AXS Smart APEX'
_diffrn_measurement_method       ω-scan
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22590
_diffrn_reflns_av_unetI/netI     0.0199
_diffrn_reflns_av_R_equivalents  0.0291
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.182
_diffrn_reflns_theta_max         27.534
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3451
_reflns_number_gt                2839
_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       'Saint+(Bruker, 2007/4)'
_computing_cell_refinement       'Saint+(Bruker, 2007/4)'
_computing_data_reduction        'Saint+(Bruker, 2007/4)'
_computing_structure_solution    'SHELXS-2016 (Sheldrick, 2016)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.0580P)²+0.5097P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   direct
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3451
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0473
_refine_ls_R_factor_gt           0.0378
_refine_ls_wR_factor_ref         0.1072
_refine_ls_wR_factor_gt          0.1000
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_restrained_S_all      1.010
_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 0.16806(4) 0.56033(3) 0.71037(3) 0.03187(13) Uani 1 1 d . . . . .
N1 N 0.46813(14) 0.68291(9) 0.59484(9) 0.0298(3) Uani 1 1 d . . . . .
C10 C 0.17474(17) 0.55706(11) 0.49829(12) 0.0302(3) Uani 1 1 d . . . . .
C7 C 0.08389(16) 0.71967(11) 0.56584(11) 0.0270(3) Uani 1 1 d . . . . .
C8 C 0.18338(17) 0.62700(11) 0.58429(11) 0.0278(3) Uani 1 1 d . . . . .
O1 O -0.22356(15) 0.95873(9) 0.52827(10) 0.0474(3) Uani 1 1 d . . . . .
O3 O 0.06850(14) 0.61080(9) 0.77517(9) 0.0430(3) Uani 1 1 d . . . . .
N2 N 0.35155(15) 0.59817(10) 0.72679(10) 0.0340(3) Uani 1 1 d . . . . .
C9 C 0.34969(17) 0.63971(11) 0.63502(11) 0.0283(3) Uani 1 1 d . . . . .
C2 C -0.11427(18) 0.88480(11) 0.54337(12) 0.0332(3) Uani 1 1 d . . . . .
N3 N 0.17045(18) 0.50156(10) 0.43210(12) 0.0427(4) Uani 1 1 d . . . . .
C3 C -0.13076(18) 0.80548(11) 0.47424(12) 0.0319(3) Uani 1 1 d . . . . .
H3 H -0.2079(16) 0.80801(13) 0.4197(11) 0.038 Uiso 1 1 calc R U . . .
C4 C -0.03339(17) 0.72310(11) 0.48616(11) 0.0291(3) Uani 1 1 d . . . . .
H4 H -0.0463(3) 0.6695(11) 0.4406(9) 0.035 Uiso 1 1 calc R U . . .
C5 C 0.00605(19) 0.88425(12) 0.62062(13) 0.0348(3) Uani 1 1 d . . . . .
H5 H 0.0207(4) 0.9390(11) 0.6653(9) 0.042 Uiso 1 1 calc R U . . .
C6 C 0.10470(18) 0.80160(11) 0.63114(12) 0.0323(3) Uani 1 1 d . . . . .
H6 H 0.1858(17) 0.80106(11) 0.6826(11) 0.039 Uiso 1 1 calc R U . . .
O2 O 0.15690(14) 0.45324(9) 0.70139(9) 0.0416(3) Uani 1 1 d . . . . .
C11 C 0.61889(18) 0.69117(13) 0.65653(13) 0.0374(4) Uani 1 1 d . . . . .
H11A H 0.7018(12) 0.69435(13) 0.6119(6) 0.045 Uiso 1 1 calc R U . . .
H11B H 0.6349(3) 0.6322(8) 0.6984(6) 0.045 Uiso 1 1 calc R U . . .
C14 C 0.5249(2) 0.65412(15) 0.41487(13) 0.0449(4) Uani 1 1 d . . . . .
H14A H 0.5146(2) 0.6847(4) 0.3473(8) 0.067 Uiso 1 1 calc R U . . .
H14B H 0.6350(13) 0.6424(2) 0.4357(3) 0.067 Uiso 1 1 calc R U . . .
H14C H 0.4690(7) 0.5904(8) 0.41295(14) 0.067 Uiso 1 1 calc R U . . .
C13 C 0.45679(19) 0.72393(13) 0.49077(12) 0.0356(4) Uani 1 1 d . . . . .
H13A H 0.5116(7) 0.7879(9) 0.49121(12) 0.043 Uiso 1 1 calc R U . . .
H13B H 0.3475(14) 0.7365(2) 0.4687(3) 0.043 Uiso 1 1 calc R U . . .
C1 C -0.2236(3) 1.03623(15) 0.60382(18) 0.0556(5) Uani 1 1 d . . . . .
H1A H -0.3080(12) 1.0849(7) 0.5840(3) 0.083 Uiso 1 1 calc R U . . .
H1B H -0.2414(4) 1.0061(4) 0.6708(10) 0.083 Uiso 1 1 calc R U . . .
H1C H -0.1215(14) 1.0713(5) 0.6089(2) 0.083 Uiso 1 1 calc R U . . .
C12 C 0.6253(2) 0.78286(18) 0.72369(17) 0.0603(6) Uani 1 1 d . . . . .
H12A H 0.7250(14) 0.78587(18) 0.7628(6) 0.090 Uiso 1 1 calc R U . . .
H12B H 0.6112(3) 0.8420(8) 0.6819(6) 0.090 Uiso 1 1 calc R U . . .
H12C H 0.5437(11) 0.77930(18) 0.7693(7) 0.090 Uiso 1 1 calc R U . . .


_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 O3 1.4256(12) . ?
S1 O2 1.4333(12) . ?
S1 N2 1.6515(13) . ?
S1 C8 1.8938(15) . ?
S1 C9 2.1899(15) . ?
N1 C9 1.3178(19) . ?
N1 C13 1.4679(19) . ?
N1 C11 1.4722(19) . ?
C10 N3 1.139(2) . ?
C10 C8 1.461(2) . ?
C7 C4 1.390(2) . ?
C7 C6 1.390(2) . ?
C7 C8 1.509(2) . ?
C8 C9 1.534(2) . ?
O1 C2 1.3632(19) . ?
O1 C1 1.432(2) . ?
N2 C9 1.3252(19) . ?
C2 C5 1.386(2) . ?
C2 C3 1.392(2) . ?
C3 C4 1.380(2) . ?
C3 H3 0.934(19) . ?
C4 H4 0.932(18) . ?
C5 C6 1.389(2) . ?
C5 H5 0.938(19) . ?
C6 H6 0.928(19) . ?
C11 C12 1.505(3) . ?
C11 H11A 0.962(13) . ?
C11 H11B 0.962(13) . ?
C14 C13 1.517(2) . ?
C14 H14A 0.974(12) . ?
C14 H14B 0.974(12) . ?
C14 H14C 0.974(12) . ?
C13 H13A 0.973(13) . ?
C13 H13B 0.973(13) . ?
C1 H1A 0.991(14) . ?
C1 H1B 0.991(14) . ?
C1 H1C 0.991(14) . ?
C12 H12A 0.961(13) . ?
C12 H12B 0.961(13) . ?
C12 H12C 0.961(13) . ?

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
O3 S1 O2 118.60(7) . . ?
O3 S1 N2 113.13(7) . . ?
O2 S1 N2 111.76(7) . . ?
O3 S1 C8 113.04(7) . . ?
O2 S1 C8 113.80(7) . . ?
N2 S1 C8 80.47(7) . . ?
O3 S1 C9 121.97(6) . . ?
O2 S1 C9 119.22(7) . . ?
N2 S1 C9 37.13(6) . . ?
C8 S1 C9 43.36(6) . . ?
C9 N1 C13 122.91(13) . . ?
C9 N1 C11 119.02(13) . . ?
C13 N1 C11 118.06(12) . . ?
N3 C10 C8 178.67(17) . . ?
C4 C7 C6 119.06(13) . . ?
C4 C7 C8 120.80(13) . . ?
C6 C7 C8 120.09(13) . . ?
C10 C8 C7 113.97(12) . . ?
C10 C8 C9 112.98(12) . . ?
C7 C8 C9 118.27(12) . . ?
C10 C8 S1 112.02(10) . . ?
C7 C8 S1 116.31(10) . . ?
C9 C8 S1 78.65(9) . . ?
C2 O1 C1 117.43(15) . . ?
C9 N2 S1 94.08(10) . . ?
N1 C9 N2 126.64(14) . . ?
N1 C9 C8 126.63(13) . . ?
N2 C9 C8 106.73(12) . . ?
N1 C9 S1 174.94(12) . . ?
N2 C9 S1 48.79(8) . . ?
C8 C9 S1 57.98(7) . . ?
O1 C2 C5 124.89(15) . . ?
O1 C2 C3 114.99(15) . . ?
C5 C2 C3 120.12(14) . . ?
C4 C3 C2 120.12(15) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C3 C4 C7 120.32(14) . . ?
C3 C4 H4 119.8 . . ?
C7 C4 H4 119.8 . . ?
C2 C5 C6 119.20(14) . . ?
C2 C5 H5 120.4 . . ?
C6 C5 H5 120.4 . . ?
C5 C6 C7 121.02(15) . . ?
C5 C6 H6 119.5 . . ?
C7 C6 H6 119.5 . . ?
N1 C11 C12 111.71(15) . . ?
N1 C11 H11A 109.3 . . ?
C12 C11 H11A 109.3 . . ?
N1 C11 H11B 109.3 . . ?
C12 C11 H11B 109.3 . . ?
H11A C11 H11B 107.9 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N1 C13 C14 112.68(14) . . ?
N1 C13 H13A 109.1 . . ?
C14 C13 H13A 109.1 . . ?
N1 C13 H13B 109.1 . . ?
C14 C13 H13B 109.1 . . ?
H13A C13 H13B 107.8 . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?

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
C4 C7 C8 C10 15.86(19) . . . . ?
C6 C7 C8 C10 -166.64(13) . . . . ?
C4 C7 C8 C9 152.26(13) . . . . ?
C6 C7 C8 C9 -30.2(2) . . . . ?
C4 C7 C8 S1 -116.79(13) . . . . ?
C6 C7 C8 S1 60.72(17) . . . . ?
O3 S1 C8 C10 -136.81(11) . . . . ?
O2 S1 C8 C10 2.32(13) . . . . ?
N2 S1 C8 C10 112.00(12) . . . . ?
C9 S1 C8 C10 110.39(13) . . . . ?
O3 S1 C8 C7 -3.28(13) . . . . ?
O2 S1 C8 C7 135.85(11) . . . . ?
N2 S1 C8 C7 -114.47(12) . . . . ?
C9 S1 C8 C7 -116.08(14) . . . . ?
O3 S1 C8 C9 112.80(9) . . . . ?
O2 S1 C8 C9 -108.07(9) . . . . ?
N2 S1 C8 C9 1.61(8) . . . . ?
O3 S1 N2 C9 -112.93(10) . . . . ?
O2 S1 N2 C9 110.10(10) . . . . ?
C8 S1 N2 C9 -1.84(9) . . . . ?
C13 N1 C9 N2 177.74(15) . . . . ?
C11 N1 C9 N2 -2.5(2) . . . . ?
C13 N1 C9 C8 -1.7(2) . . . . ?
C11 N1 C9 C8 178.04(14) . . . . ?
S1 N2 C9 N1 -177.21(14) . . . . ?
S1 N2 C9 C8 2.34(12) . . . . ?
C10 C8 C9 N1 68.19(19) . . . . ?
C7 C8 C9 N1 -68.61(19) . . . . ?
S1 C8 C9 N1 177.48(14) . . . . ?
C10 C8 C9 N2 -111.36(14) . . . . ?
C7 C8 C9 N2 111.84(14) . . . . ?
S1 C8 C9 N2 -2.07(11) . . . . ?
C10 C8 C9 S1 -109.28(12) . . . . ?
C7 C8 C9 S1 113.91(13) . . . . ?
C1 O1 C2 C5 -6.7(2) . . . . ?
C1 O1 C2 C3 172.86(15) . . . . ?
O1 C2 C3 C4 -175.59(14) . . . . ?
C5 C2 C3 C4 4.0(2) . . . . ?
C2 C3 C4 C7 -1.4(2) . . . . ?
C6 C7 C4 C3 -2.0(2) . . . . ?
C8 C7 C4 C3 175.50(13) . . . . ?
O1 C2 C5 C6 176.43(15) . . . . ?
C3 C2 C5 C6 -3.2(2) . . . . ?
C2 C5 C6 C7 -0.3(2) . . . . ?
C4 C7 C6 C5 2.9(2) . . . . ?
C8 C7 C6 C5 -174.64(14) . . . . ?
C9 N1 C11 C12 -85.10(19) . . . . ?
C13 N1 C11 C12 94.66(18) . . . . ?
C9 N1 C13 C14 -100.47(17) . . . . ?
C11 N1 C13 C14 79.77(18) . . . . ?

_refine_diff_density_max         0.279
_refine_diff_density_min         -0.265
_refine_diff_density_rms         0.046



####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_B_100
_database_code_depnum_ccdc_archive 'CCDC 1821390'
_audit_update_record             
;
2018-02-02 deposited with the CCDC.
2018-11-08 downloaded from the CCDC.
;
_audit_creation_date             2016-04-18
_audit_creation_method           SHELXL-2016/6
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.5
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
#------------------ CHEMICAL INFORMATION ------------------------------------# 
_chemical_name_systematic        
3-Diethylamino-4-(4-methoxyphenyl)-1,1-dioxo-4H-1λ⁶,2-thiazete-4-carbonitrile
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H17 N3 O3 S'
_chemical_formula_sum            'C14 H17 N3 O3 S'
_chemical_formula_weight         307.36

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.27650(10)
_cell_length_b                   17.2288(3)
_cell_length_c                   10.3944(2)
_cell_angle_alpha                90
_cell_angle_beta                 94.9855(6)
_cell_angle_gamma                90
_cell_volume                     1476.57(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7132
_cell_measurement_theta_min      2.2945
_cell_measurement_theta_max      27.4705

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.383
_exptl_crystal_F_000             648
_exptl_transmission_factor_min   0.8753
_exptl_transmission_factor_max   0.9459
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.175
_exptl_crystal_size_min          0.15
_exptl_absorpt_coefficient_mu    0.233
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.8753
_exptl_absorpt_correction_T_max  0.9459
_exptl_absorpt_process_details   'SADABS-2007/4, Bruker'
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed X-ray tube'
_diffrn_measurement_device_type  'Bruker AXS Smart APEX'
_diffrn_measurement_method       ω-scan
_diffrn_reflns_number            22043
_diffrn_reflns_av_unetI/netI     0.0188
_diffrn_reflns_av_R_equivalents  0.0284
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.295
_diffrn_reflns_theta_max         27.536
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3410
_reflns_number_gt                2846
_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       'Saint+(Bruker, 2007/4)'
_computing_cell_refinement       'Saint+(Bruker, 2007/4)'
_computing_data_reduction        'Saint+(Bruker, 2007/4)'
_computing_structure_solution    'SHELXS-2016 (Sheldrick, 2016)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.0444P)²+0.9253P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   direct
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3410
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0451
_refine_ls_R_factor_gt           0.0358
_refine_ls_wR_factor_ref         0.0944
_refine_ls_wR_factor_gt          0.0884
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_restrained_S_all      1.006
_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 0.97001(4) 0.80151(2) 0.39831(4) 0.02186(11) Uani 1 1 d . . . . .
O2 O 1.08037(13) 0.80669(7) 0.51234(11) 0.0285(3) Uani 1 1 d . . . . .
O3 O 1.03829(13) 0.79144(6) 0.27756(11) 0.0275(3) Uani 1 1 d . . . . .
N1 N 0.55729(15) 0.79787(7) 0.44419(12) 0.0197(3) Uani 1 1 d . . . . .
O1 O 0.67958(13) 0.99506(6) -0.11323(9) 0.0244(2) Uani 1 1 d . . . . .
C8 C 0.80423(16) 0.87586(8) 0.39242(13) 0.0183(3) Uani 1 1 d . . . . .
N2 N 0.81511(15) 0.74339(7) 0.41787(13) 0.0243(3) Uani 1 1 d . . . . .
C7 C 0.76199(16) 0.91110(8) 0.26025(13) 0.0180(3) Uani 1 1 d . . . . .
C2 C 0.70792(17) 0.97181(8) 0.01159(13) 0.0193(3) Uani 1 1 d . . . . .
C6 C 0.67871(17) 0.86767(8) 0.16223(14) 0.0205(3) Uani 1 1 d . . . . .
H6 H 0.6413(7) 0.8173(10) 0.1802(4) 0.025 Uiso 1 1 calc R U . . .
C9 C 0.71042(17) 0.80208(8) 0.42283(13) 0.0192(3) Uani 1 1 d . . . . .
C10 C 0.82305(17) 0.93316(9) 0.49603(14) 0.0208(3) Uani 1 1 d . . . . .
C12 C 0.4242(2) 0.68868(10) 0.32250(16) 0.0283(3) Uani 1 1 d . . . . .
H12A H 0.3724(6) 0.6367(6) 0.33255(18) 0.042 Uiso 1 1 calc R U . . .
H12B H 0.3435(9) 0.7250(4) 0.2772(5) 0.042 Uiso 1 1 calc R U . . .
H12C H 0.5199(11) 0.68294(12) 0.2703(6) 0.042 Uiso 1 1 calc R U . . .
C5 C 0.65072(18) 0.89792(8) 0.03930(14) 0.0215(3) Uani 1 1 d . . . . .
H5 H 0.5907(11) 0.8675(6) -0.0286(13) 0.026 Uiso 1 1 calc R U . . .
C3 C 0.78786(18) 1.01597(9) 0.10902(14) 0.0214(3) Uani 1 1 d . . . . .
H3 H 0.8235(7) 1.0668(10) 0.0914(4) 0.026 Uiso 1 1 calc R U . . .
C4 C 0.81540(17) 0.98517(8) 0.23288(14) 0.0207(3) Uani 1 1 d . . . . .
H4 H 0.8710(11) 1.0150(6) 0.2989(13) 0.025 Uiso 1 1 calc R U . . .
C11 C 0.48002(19) 0.72107(9) 0.45473(14) 0.0239(3) Uani 1 1 d . . . . .
H11A H 0.3883(12) 0.72575(10) 0.5052(7) 0.029 Uiso 1 1 calc R U . . .
H11B H 0.5562(10) 0.6857(5) 0.4987(6) 0.029 Uiso 1 1 calc R U . . .
C13 C 0.45888(18) 0.86736(9) 0.46536(14) 0.0229(3) Uani 1 1 d . . . . .
H13A H 0.3479(14) 0.85968(12) 0.4243(5) 0.027 Uiso 1 1 calc R U . . .
H13B H 0.5063(6) 0.9127(6) 0.4243(5) 0.027 Uiso 1 1 calc R U . . .
N3 N 0.83640(17) 0.97875(8) 0.57639(13) 0.0292(3) Uani 1 1 d . . . . .
C1 C 0.7498(2) 1.06739(9) -0.14697(15) 0.0260(3) Uani 1 1 d . . . . .
H1A H 0.7214(4) 1.07801(15) -0.2385(10) 0.039 Uiso 1 1 calc R U . . .
H1B H 0.7082(5) 1.1090(5) -0.0951(6) 0.039 Uiso 1 1 calc R U . . .
H1C H 0.8676(13) 1.06455(9) -0.1303(2) 0.039 Uiso 1 1 calc R U . . .
C14 C 0.4515(2) 0.88331(10) 0.60881(16) 0.0299(4) Uani 1 1 d . . . . .
H14A H 0.3854(8) 0.9297(5) 0.6200(2) 0.045 Uiso 1 1 calc R U . . .
H14B H 0.4027(6) 0.8387(5) 0.6495(5) 0.045 Uiso 1 1 calc R U . . .
H14C H 0.5615(13) 0.89182(14) 0.6494(5) 0.045 Uiso 1 1 calc R U . . .


_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 O3 1.4311(11) . ?
S1 O2 1.4349(12) . ?
S1 N2 1.6532(13) . ?
S1 C8 1.8742(14) . ?
S1 C9 2.1855(15) . ?
N1 C9 1.3076(19) . ?
N1 C11 1.4778(18) . ?
N1 C13 1.4751(18) . ?
O1 C2 1.3587(17) . ?
O1 C1 1.4314(18) . ?
C8 C10 1.459(2) . ?
C8 C7 1.5149(19) . ?
C8 C9 1.5366(19) . ?
N2 C9 1.3355(19) . ?
C7 C4 1.388(2) . ?
C7 C6 1.397(2) . ?
C2 C3 1.388(2) . ?
C2 C5 1.397(2) . ?
C6 C5 1.381(2) . ?
C6 H6 0.946(18) . ?
C10 N3 1.145(2) . ?
C12 C11 1.518(2) . ?
C12 H12A 1.003(11) . ?
C12 H12B 1.003(11) . ?
C12 H12C 1.003(11) . ?
C5 H5 0.979(18) . ?
C3 C4 1.393(2) . ?
C3 H3 0.947(18) . ?
C4 H4 0.944(18) . ?
C11 H11A 0.963(13) . ?
C11 H11B 0.963(13) . ?
C13 C14 1.523(2) . ?
C13 H13A 0.988(12) . ?
C13 H13B 0.988(12) . ?
C1 H1A 0.977(10) . ?
C1 H1B 0.977(10) . ?
C1 H1C 0.977(10) . ?
C14 H14A 0.981(11) . ?
C14 H14B 0.981(11) . ?
C14 H14C 0.981(11) . ?

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
O3 S1 O2 117.42(7) . . ?
O3 S1 N2 113.83(7) . . ?
O2 S1 N2 112.39(7) . . ?
O3 S1 C8 113.45(6) . . ?
O2 S1 C8 113.33(7) . . ?
N2 S1 C8 81.06(6) . . ?
O3 S1 C9 124.75(6) . . ?
O2 S1 C9 117.71(6) . . ?
N2 S1 C9 37.59(6) . . ?
C8 S1 C9 43.65(5) . . ?
C9 N1 C11 119.62(12) . . ?
C9 N1 C13 122.43(12) . . ?
C11 N1 C13 117.87(12) . . ?
C2 O1 C1 116.79(11) . . ?
C10 C8 C7 113.56(12) . . ?
C10 C8 C9 115.55(11) . . ?
C7 C8 C9 115.92(12) . . ?
C10 C8 S1 114.04(10) . . ?
C7 C8 S1 114.46(9) . . ?
C9 C8 S1 79.02(8) . . ?
C9 N2 S1 93.37(10) . . ?
C4 C7 C6 119.26(13) . . ?
C4 C7 C8 120.12(13) . . ?
C6 C7 C8 120.48(13) . . ?
O1 C2 C3 124.54(13) . . ?
O1 C2 C5 115.61(13) . . ?
C3 C2 C5 119.86(13) . . ?
C5 C6 C7 120.36(13) . . ?
C5 C6 H6 119.8 . . ?
C7 C6 H6 119.8 . . ?
N1 C9 N2 127.32(13) . . ?
N1 C9 C8 126.54(12) . . ?
N2 C9 C8 106.10(12) . . ?
N1 C9 S1 175.38(11) . . ?
N2 C9 S1 49.04(7) . . ?
C8 C9 S1 57.34(7) . . ?
N3 C10 C8 179.09(16) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C6 C5 C2 120.14(13) . . ?
C6 C5 H5 119.9 . . ?
C2 C5 H5 119.9 . . ?
C2 C3 C4 119.66(13) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C7 C4 C3 120.69(13) . . ?
C7 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
N1 C11 C12 111.20(12) . . ?
N1 C11 H11A 109.4 . . ?
C12 C11 H11A 109.4 . . ?
N1 C11 H11B 109.4 . . ?
C12 C11 H11B 109.4 . . ?
H11A C11 H11B 108.0 . . ?
N1 C13 C14 111.24(12) . . ?
N1 C13 H13A 109.4 . . ?
C14 C13 H13A 109.4 . . ?
N1 C13 H13B 109.4 . . ?
C14 C13 H13B 109.4 . . ?
H13A C13 H13B 108.0 . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

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
O3 S1 C8 C10 -130.32(10) . . . . ?
O2 S1 C8 C10 6.88(12) . . . . ?
N2 S1 C8 C10 117.49(11) . . . . ?
C9 S1 C8 C10 113.24(13) . . . . ?
O3 S1 C8 C7 2.81(13) . . . . ?
O2 S1 C8 C7 140.01(10) . . . . ?
N2 S1 C8 C7 -109.38(11) . . . . ?
C9 S1 C8 C7 -113.64(13) . . . . ?
O3 S1 C8 C9 116.44(9) . . . . ?
O2 S1 C8 C9 -106.35(9) . . . . ?
N2 S1 C8 C9 4.26(8) . . . . ?
O3 S1 N2 C9 -116.60(10) . . . . ?
O2 S1 N2 C9 106.83(10) . . . . ?
C8 S1 N2 C9 -4.82(9) . . . . ?
C10 C8 C7 C4 29.99(18) . . . . ?
C9 C8 C7 C4 167.30(13) . . . . ?
S1 C8 C7 C4 -103.36(14) . . . . ?
C10 C8 C7 C6 -154.37(13) . . . . ?
C9 C8 C7 C6 -17.06(18) . . . . ?
S1 C8 C7 C6 72.28(15) . . . . ?
C1 O1 C2 C3 5.5(2) . . . . ?
C1 O1 C2 C5 -174.40(13) . . . . ?
C4 C7 C6 C5 0.4(2) . . . . ?
C8 C7 C6 C5 -175.28(13) . . . . ?
C11 N1 C9 N2 -5.3(2) . . . . ?
C13 N1 C9 N2 171.32(14) . . . . ?
C11 N1 C9 C8 171.79(13) . . . . ?
C13 N1 C9 C8 -11.5(2) . . . . ?
S1 N2 C9 N1 -176.34(14) . . . . ?
S1 N2 C9 C8 6.05(11) . . . . ?
C10 C8 C9 N1 65.41(19) . . . . ?
C7 C8 C9 N1 -71.05(18) . . . . ?
S1 C8 C9 N1 176.95(14) . . . . ?
C10 C8 C9 N2 -116.96(13) . . . . ?
C7 C8 C9 N2 106.58(14) . . . . ?
S1 C8 C9 N2 -5.42(10) . . . . ?
C10 C8 C9 S1 -111.54(12) . . . . ?
C7 C8 C9 S1 112.00(12) . . . . ?
C7 C6 C5 C2 1.0(2) . . . . ?
O1 C2 C5 C6 177.57(13) . . . . ?
C3 C2 C5 C6 -2.4(2) . . . . ?
O1 C2 C3 C4 -177.69(13) . . . . ?
C5 C2 C3 C4 2.2(2) . . . . ?
C6 C7 C4 C3 -0.5(2) . . . . ?
C8 C7 C4 C3 175.17(13) . . . . ?
C2 C3 C4 C7 -0.8(2) . . . . ?
C9 N1 C11 C12 -83.69(17) . . . . ?
C13 N1 C11 C12 99.49(15) . . . . ?
C9 N1 C13 C14 -96.14(16) . . . . ?
C11 N1 C13 C14 80.58(16) . . . . ?

_refine_diff_density_max         0.321
_refine_diff_density_min         -0.379
_refine_diff_density_rms         0.049



_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: Water'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_A_292
_database_code_depnum_ccdc_archive 'CCDC 1821389'
_audit_update_record             
;
2018-02-01 deposited with the CCDC.
2018-11-08 downloaded from the CCDC.
;
_audit_creation_date             2016-04-18
_audit_creation_method           SHELXL-2016/6
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.5
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
#------------------ CHEMICAL INFORMATION ------------------------------------# 
_chemical_name_systematic        
;
'3-Diethylamino-4-(4-methoxyphenyl)-1,1-dioxo-4H-1λ⁶
,2-thiazete-4-carbonitrile'
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H17 N3 O3 S'
_chemical_formula_sum            'C14 H17 N3 O3 S'
_chemical_formula_weight         307.36

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.6335(2)
_cell_length_b                   13.3739(3)
_cell_length_c                   13.2075(2)
_cell_angle_alpha                90
_cell_angle_beta                 94.6615(9)
_cell_angle_gamma                90
_cell_volume                     1519.94(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    292(2)
_cell_measurement_reflns_used    5308
_cell_measurement_theta_min      2.7195
_cell_measurement_theta_max      23.817

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_F_000             648
_exptl_transmission_factor_min   0.9081
_exptl_transmission_factor_max   0.9395
_exptl_crystal_size_max          0.275
_exptl_crystal_size_mid          0.179
_exptl_crystal_size_min          0.125
_exptl_absorpt_coefficient_mu    0.226
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.9081
_exptl_absorpt_correction_T_max  0.9395
_exptl_absorpt_process_details   'SADABS-2007/4, Bruker'
_diffrn_ambient_temperature      292(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed X-ray tube'
_diffrn_measurement_device_type  'Bruker AXS Smart APEX'
_diffrn_measurement_method       ω-scan
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23025
_diffrn_reflns_av_unetI/netI     0.0224
_diffrn_reflns_av_R_equivalents  0.0308
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.171
_diffrn_reflns_theta_max         27.503
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3498
_reflns_number_gt                2721
_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       'Saint+(Bruker, 2007/4)'
_computing_cell_refinement       'Saint+(Bruker, 2007/4)'
_computing_data_reduction        'Saint+(Bruker, 2007/4)'
_computing_structure_solution    'SHELXS-2016 (Sheldrick, 2016)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.0604P)²+0.4339P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   direct
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3498
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0565
_refine_ls_R_factor_gt           0.0413
_refine_ls_wR_factor_ref         0.1169
_refine_ls_wR_factor_gt          0.1061
_refine_ls_goodness_of_fit_ref   0.992
_refine_ls_restrained_S_all      0.992
_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 0.16770(5) 0.55969(3) 0.70998(3) 0.04499(15) Uani 1 1 d . . . . .
N1 N 0.46616(16) 0.68285(10) 0.59572(10) 0.0414(3) Uani 1 1 d . . . . .
C10 C 0.17512(19) 0.55776(12) 0.49925(13) 0.0419(4) Uani 1 1 d . . . . .
C7 C 0.08381(18) 0.71932(12) 0.56729(12) 0.0367(3) Uani 1 1 d . . . . .
C8 C 0.18311(18) 0.62707(12) 0.58515(12) 0.0375(3) Uani 1 1 d . . . . .
O1 O -0.21950(18) 0.95803(11) 0.52977(12) 0.0681(4) Uani 1 1 d . . . . .
O3 O 0.06843(16) 0.60915(11) 0.77487(10) 0.0605(4) Uani 1 1 d . . . . .
N2 N 0.34976(17) 0.59745(12) 0.72639(11) 0.0476(4) Uani 1 1 d . . . . .
C9 C 0.34774(19) 0.63939(12) 0.63529(12) 0.0391(4) Uani 1 1 d . . . . .
C2 C -0.1116(2) 0.88373(12) 0.54531(14) 0.0461(4) Uani 1 1 d . . . . .
N3 N 0.1717(2) 0.50282(12) 0.43350(14) 0.0590(4) Uani 1 1 d . . . . .
C3 C -0.1278(2) 0.80552(13) 0.47608(14) 0.0444(4) Uani 1 1 d . . . . .
H3 H -0.2036(17) 0.80858(15) 0.4216(12) 0.053 Uiso 1 1 calc R U . . .
C4 C -0.03153(19) 0.72328(13) 0.48800(12) 0.0402(4) Uani 1 1 d . . . . .
H4 H -0.0441(3) 0.6702(11) 0.4426(10) 0.048 Uiso 1 1 calc R U . . .
C5 C 0.0064(2) 0.88254(13) 0.62242(14) 0.0489(4) Uani 1 1 d . . . . .
H5 H 0.0202(4) 0.9359(12) 0.6664(10) 0.059 Uiso 1 1 calc R U . . .
C6 C 0.1038(2) 0.80026(13) 0.63286(13) 0.0444(4) Uani 1 1 d . . . . .
H6 H 0.1842(18) 0.79921(13) 0.6848(11) 0.053 Uiso 1 1 calc R U . . .
O2 O 0.15719(16) 0.45325(10) 0.70030(10) 0.0580(4) Uani 1 1 d . . . . .
C11 C 0.6161(2) 0.69038(15) 0.65670(14) 0.0527(5) Uani 1 1 d . . . . .
H11A H 0.6983(13) 0.69399(16) 0.6120(7) 0.063 Uiso 1 1 calc R U . . .
H11B H 0.6319(3) 0.6312(9) 0.6974(6) 0.063 Uiso 1 1 calc R U . . .
C14 C 0.5234(3) 0.65547(18) 0.41656(15) 0.0636(6) Uani 1 1 d . . . . .
H14A H 0.5131(3) 0.6865(4) 0.3495(9) 0.095 Uiso 1 1 calc R U . . .
H14B H 0.6330(15) 0.6439(2) 0.4369(3) 0.095 Uiso 1 1 calc R U . . .
H14C H 0.4680(8) 0.5919(9) 0.41418(16) 0.095 Uiso 1 1 calc R U . . .
C13 C 0.4552(2) 0.72406(15) 0.49273(14) 0.0497(4) Uani 1 1 d . . . . .
H13A H 0.5090(8) 0.7873(9) 0.49353(14) 0.060 Uiso 1 1 calc R U . . .
H13B H 0.3476(15) 0.7364(2) 0.4713(3) 0.060 Uiso 1 1 calc R U . . .
C1 C -0.2217(3) 1.03478(18) 0.6041(2) 0.0797(7) Uani 1 1 d . . . . .
H1A H -0.3070(14) 1.0846(8) 0.5829(4) 0.120 Uiso 1 1 calc R U . . .
H1B H -0.2422(4) 1.0042(5) 0.6721(11) 0.120 Uiso 1 1 calc R U . . .
H1C H -0.1176(17) 1.0704(6) 0.6104(2) 0.120 Uiso 1 1 calc R U . . .
C12 C 0.6237(3) 0.7801(2) 0.7245(2) 0.0844(8) Uani 1 1 d . . . . .
H12A H 0.7198(16) 0.7822(2) 0.7616(7) 0.127 Uiso 1 1 calc R U . . .
H12B H 0.6105(4) 0.8376(10) 0.6853(6) 0.127 Uiso 1 1 calc R U . . .
H12C H 0.5456(13) 0.7763(2) 0.7687(8) 0.127 Uiso 1 1 calc R U . . .


_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 O3 1.4234(14) . ?
S1 O2 1.4315(14) . ?
S1 N2 1.6484(15) . ?
S1 C8 1.8930(16) . ?
S1 C9 2.1851(17) . ?
N1 C9 1.320(2) . ?
N1 C13 1.464(2) . ?
N1 C11 1.471(2) . ?
C10 N3 1.136(2) . ?
C10 C8 1.462(2) . ?
C7 C4 1.386(2) . ?
C7 C6 1.388(2) . ?
C7 C8 1.510(2) . ?
C8 C9 1.527(2) . ?
O1 C2 1.366(2) . ?
O1 C1 1.422(3) . ?
N2 C9 1.326(2) . ?
C2 C5 1.381(3) . ?
C2 C3 1.389(2) . ?
C3 C4 1.380(2) . ?
C3 H3 0.93(2) . ?
C4 H4 0.930(19) . ?
C5 C6 1.385(2) . ?
C5 H5 0.92(2) . ?
C6 H6 0.94(2) . ?
C11 C12 1.495(3) . ?
C11 H11A 0.960(14) . ?
C11 H11B 0.960(14) . ?
C14 C13 1.515(3) . ?
C14 H14A 0.975(13) . ?
C14 H14B 0.975(13) . ?
C14 H14C 0.975(13) . ?
C13 H13A 0.964(14) . ?
C13 H13B 0.964(14) . ?
C1 H1A 1.015(16) . ?
C1 H1B 1.015(16) . ?
C1 H1C 1.015(16) . ?
C12 H12A 0.929(15) . ?
C12 H12B 0.929(15) . ?
C12 H12C 0.929(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
O3 S1 O2 118.62(8) . . ?
O3 S1 N2 113.13(9) . . ?
O2 S1 N2 111.67(8) . . ?
O3 S1 C8 113.05(8) . . ?
O2 S1 C8 113.84(8) . . ?
N2 S1 C8 80.50(7) . . ?
O3 S1 C9 122.03(7) . . ?
O2 S1 C9 119.15(7) . . ?
N2 S1 C9 37.27(7) . . ?
C8 S1 C9 43.25(6) . . ?
C9 N1 C13 122.70(15) . . ?
C9 N1 C11 119.26(14) . . ?
C13 N1 C11 118.05(14) . . ?
N3 C10 C8 178.49(19) . . ?
C4 C7 C6 119.12(15) . . ?
C4 C7 C8 120.87(14) . . ?
C6 C7 C8 119.97(15) . . ?
C10 C8 C7 113.98(14) . . ?
C10 C8 C9 112.85(13) . . ?
C7 C8 C9 118.43(13) . . ?
C10 C8 S1 111.82(11) . . ?
C7 C8 S1 116.48(11) . . ?
C9 C8 S1 78.61(9) . . ?
C2 O1 C1 117.96(18) . . ?
C9 N2 S1 93.91(11) . . ?
N1 C9 N2 126.27(16) . . ?
N1 C9 C8 126.81(15) . . ?
N2 C9 C8 106.91(14) . . ?
N1 C9 S1 174.63(13) . . ?
N2 C9 S1 48.82(8) . . ?
C8 C9 S1 58.13(8) . . ?
O1 C2 C5 124.92(17) . . ?
O1 C2 C3 114.73(17) . . ?
C5 C2 C3 120.35(16) . . ?
C4 C3 C2 119.87(17) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C3 C4 C7 120.37(16) . . ?
C3 C4 H4 119.8 . . ?
C7 C4 H4 119.8 . . ?
C2 C5 C6 119.23(17) . . ?
C2 C5 H5 120.4 . . ?
C6 C5 H5 120.4 . . ?
C5 C6 C7 120.92(17) . . ?
C5 C6 H6 119.5 . . ?
C7 C6 H6 119.5 . . ?
N1 C11 C12 112.12(17) . . ?
N1 C11 H11A 109.2 . . ?
C12 C11 H11A 109.2 . . ?
N1 C11 H11B 109.2 . . ?
C12 C11 H11B 109.2 . . ?
H11A C11 H11B 107.9 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N1 C13 C14 112.95(16) . . ?
N1 C13 H13A 109.0 . . ?
C14 C13 H13A 109.0 . . ?
N1 C13 H13B 109.0 . . ?
C14 C13 H13B 109.0 . . ?
H13A C13 H13B 107.8 . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?

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
C4 C7 C8 C10 15.4(2) . . . . ?
C6 C7 C8 C10 -166.88(15) . . . . ?
C4 C7 C8 C9 151.79(15) . . . . ?
C6 C7 C8 C9 -30.5(2) . . . . ?
C4 C7 C8 S1 -117.13(14) . . . . ?
C6 C7 C8 S1 60.59(19) . . . . ?
O3 S1 C8 C10 -136.87(12) . . . . ?
O2 S1 C8 C10 2.33(15) . . . . ?
N2 S1 C8 C10 111.93(13) . . . . ?
C9 S1 C8 C10 110.24(15) . . . . ?
O3 S1 C8 C7 -3.36(15) . . . . ?
O2 S1 C8 C7 135.84(12) . . . . ?
N2 S1 C8 C7 -114.56(13) . . . . ?
C9 S1 C8 C7 -116.25(15) . . . . ?
O3 S1 C8 C9 112.89(10) . . . . ?
O2 S1 C8 C9 -107.91(10) . . . . ?
N2 S1 C8 C9 1.69(9) . . . . ?
O3 S1 N2 C9 -113.02(11) . . . . ?
O2 S1 N2 C9 110.08(11) . . . . ?
C8 S1 N2 C9 -1.91(11) . . . . ?
C13 N1 C9 N2 177.62(17) . . . . ?
C11 N1 C9 N2 -2.2(3) . . . . ?
C13 N1 C9 C8 -1.9(3) . . . . ?
C11 N1 C9 C8 178.27(15) . . . . ?
S1 N2 C9 N1 -177.20(15) . . . . ?
S1 N2 C9 C8 2.44(13) . . . . ?
C10 C8 C9 N1 68.4(2) . . . . ?
C7 C8 C9 N1 -68.4(2) . . . . ?
S1 C8 C9 N1 177.47(16) . . . . ?
C10 C8 C9 N2 -111.22(16) . . . . ?
C7 C8 C9 N2 111.93(16) . . . . ?
S1 C8 C9 N2 -2.16(12) . . . . ?
C10 C8 C9 S1 -109.06(13) . . . . ?
C7 C8 C9 S1 114.09(14) . . . . ?
C1 O1 C2 C5 -7.1(3) . . . . ?
C1 O1 C2 C3 172.87(18) . . . . ?
O1 C2 C3 C4 -175.93(15) . . . . ?
C5 C2 C3 C4 4.0(3) . . . . ?
C2 C3 C4 C7 -1.6(2) . . . . ?
C6 C7 C4 C3 -1.7(2) . . . . ?
C8 C7 C4 C3 176.05(15) . . . . ?
O1 C2 C5 C6 176.86(17) . . . . ?
C3 C2 C5 C6 -3.1(3) . . . . ?
C2 C5 C6 C7 -0.2(3) . . . . ?
C4 C7 C6 C5 2.6(3) . . . . ?
C8 C7 C6 C5 -175.13(15) . . . . ?
C9 N1 C11 C12 -85.0(2) . . . . ?
C13 N1 C11 C12 95.2(2) . . . . ?
C9 N1 C13 C14 -100.46(19) . . . . ?
C11 N1 C13 C14 79.3(2) . . . . ?

_refine_diff_density_max         0.272
_refine_diff_density_min         -0.254
_refine_diff_density_rms         0.041



####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_B_120
_database_code_depnum_ccdc_archive 'CCDC 1821393'
_audit_update_record             
;
2018-02-02 deposited with the CCDC.
2018-11-08 downloaded from the CCDC.
;
_audit_creation_date             2016-04-18
_audit_creation_method           SHELXL-2016/6
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.5
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
#------------------ CHEMICAL INFORMATION ------------------------------------# 
_chemical_name_systematic        
3-Diethylamino-4-(4-methoxyphenyl)-1,1-dioxo-4H-1λ⁶,2-thiazete-4-carbonitrile
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H17 N3 O3 S'
_chemical_formula_sum            'C14 H17 N3 O3 S'
_chemical_formula_weight         307.36

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.2852(2)
_cell_length_b                   17.2551(3)
_cell_length_c                   10.3985(2)
_cell_angle_alpha                90
_cell_angle_beta                 94.9870(8)
_cell_angle_gamma                90
_cell_volume                     1480.96(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    6838
_cell_measurement_theta_min      2.293
_cell_measurement_theta_max      27.443

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.379
_exptl_crystal_F_000             648
_exptl_transmission_factor_min   0.8796
_exptl_transmission_factor_max   0.9459
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.175
_exptl_crystal_size_min          0.15
_exptl_absorpt_coefficient_mu    0.232
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.8796
_exptl_absorpt_correction_T_max  0.9459
_exptl_absorpt_process_details   'SADABS-2007/4, Bruker'
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed X-ray tube'
_diffrn_measurement_device_type  'Bruker AXS Smart APEX'
_diffrn_measurement_method       ω-scan
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22108
_diffrn_reflns_av_unetI/netI     0.0191
_diffrn_reflns_av_R_equivalents  0.0289
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.293
_diffrn_reflns_theta_max         27.537
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3418
_reflns_number_gt                2830
_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       'Saint+(Bruker, 2007/4)'
_computing_cell_refinement       'Saint+(Bruker, 2007/4)'
_computing_data_reduction        'Saint+(Bruker, 2007/4)'
_computing_structure_solution    'SHELXS-2016 (Sheldrick, 2016)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.0464P)²+0.7802P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   direct
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3418
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0460
_refine_ls_R_factor_gt           0.0358
_refine_ls_wR_factor_ref         0.0968
_refine_ls_wR_factor_gt          0.0900
_refine_ls_goodness_of_fit_ref   1.018
_refine_ls_restrained_S_all      1.018
_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 0.96980(4) 0.80152(2) 0.39827(4) 0.02476(11) Uani 1 1 d . . . . .
O2 O 1.08012(13) 0.80670(7) 0.51207(11) 0.0326(3) Uani 1 1 d . . . . .
O3 O 1.03778(14) 0.79143(7) 0.27760(11) 0.0314(3) Uani 1 1 d . . . . .
N1 N 0.55764(15) 0.79790(7) 0.44406(12) 0.0220(3) Uani 1 1 d . . . . .
O1 O 0.67984(14) 0.99492(6) -0.11295(10) 0.0281(2) Uani 1 1 d . . . . .
C8 C 0.80414(16) 0.87586(8) 0.39238(13) 0.0204(3) Uani 1 1 d . . . . .
N2 N 0.81524(15) 0.74356(8) 0.41787(13) 0.0276(3) Uani 1 1 d . . . . .
C7 C 0.76217(16) 0.91096(8) 0.26031(13) 0.0200(3) Uani 1 1 d . . . . .
C2 C 0.70789(17) 0.97164(8) 0.01199(13) 0.0214(3) Uani 1 1 d . . . . .
C6 C 0.67934(17) 0.86768(8) 0.16214(14) 0.0228(3) Uani 1 1 d . . . . .
H6 H 0.6425(7) 0.8176(10) 0.1798(4) 0.027 Uiso 1 1 calc R U . . .
C9 C 0.71052(18) 0.80229(8) 0.42270(13) 0.0217(3) Uani 1 1 d . . . . .
C10 C 0.82321(17) 0.93299(9) 0.49609(14) 0.0235(3) Uani 1 1 d . . . . .
C12 C 0.4247(2) 0.68882(10) 0.32251(16) 0.0322(4) Uani 1 1 d . . . . .
H12A H 0.3727(6) 0.6367(6) 0.33274(19) 0.048 Uiso 1 1 calc R U . . .
H12B H 0.3438(10) 0.7252(4) 0.2770(6) 0.048 Uiso 1 1 calc R U . . .
H12C H 0.5207(11) 0.68299(12) 0.2702(6) 0.048 Uiso 1 1 calc R U . . .
C5 C 0.65129(18) 0.89785(9) 0.03952(14) 0.0239(3) Uani 1 1 d . . . . .
H5 H 0.5915(11) 0.8674(6) -0.0284(13) 0.029 Uiso 1 1 calc R U . . .
C3 C 0.78759(18) 1.01569(9) 0.10925(14) 0.0242(3) Uani 1 1 d . . . . .
H3 H 0.8228(7) 1.0660(10) 0.0918(4) 0.029 Uiso 1 1 calc R U . . .
C4 C 0.81514(18) 0.98497(8) 0.23294(14) 0.0230(3) Uani 1 1 d . . . . .
H4 H 0.8696(11) 1.0143(6) 0.2979(13) 0.028 Uiso 1 1 calc R U . . .
C11 C 0.48035(19) 0.72126(9) 0.45449(15) 0.0270(3) Uani 1 1 d . . . . .
H11A H 0.3889(12) 0.72597(11) 0.5048(7) 0.032 Uiso 1 1 calc R U . . .
H11B H 0.5562(10) 0.6860(5) 0.4984(6) 0.032 Uiso 1 1 calc R U . . .
C13 C 0.45902(18) 0.86715(9) 0.46503(15) 0.0259(3) Uani 1 1 d . . . . .
H13A H 0.3495(14) 0.85939(13) 0.4246(5) 0.031 Uiso 1 1 calc R U . . .
H13B H 0.5055(6) 0.9118(6) 0.4243(6) 0.031 Uiso 1 1 calc R U . . .
N3 N 0.83654(17) 0.97837(9) 0.57635(13) 0.0333(3) Uani 1 1 d . . . . .
C1 C 0.7498(2) 1.06714(9) -0.14657(15) 0.0295(3) Uani 1 1 d . . . . .
H1A H 0.7216(4) 1.07773(15) -0.2382(10) 0.044 Uiso 1 1 calc R U . . .
H1B H 0.7079(5) 1.1087(5) -0.0948(6) 0.044 Uiso 1 1 calc R U . . .
H1C H 0.8676(13) 1.06439(9) -0.1297(2) 0.044 Uiso 1 1 calc R U . . .
C14 C 0.4515(2) 0.88330(10) 0.60808(16) 0.0342(4) Uani 1 1 d . . . . .
H14A H 0.3854(8) 0.9294(5) 0.6189(2) 0.051 Uiso 1 1 calc R U . . .
H14B H 0.4032(6) 0.8389(5) 0.6488(5) 0.051 Uiso 1 1 calc R U . . .
H14C H 0.5611(13) 0.89198(14) 0.6485(5) 0.051 Uiso 1 1 calc R U . . .


_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 O3 1.4300(12) . ?
S1 O2 1.4338(12) . ?
S1 N2 1.6514(13) . ?
S1 C8 1.8757(14) . ?
S1 C9 2.1850(15) . ?
N1 C9 1.3070(19) . ?
N1 C13 1.4745(18) . ?
N1 C11 1.4774(19) . ?
O1 C2 1.3604(17) . ?
O1 C1 1.4304(18) . ?
C8 C10 1.459(2) . ?
C8 C7 1.5134(19) . ?
C8 C9 1.5347(19) . ?
N2 C9 1.3379(19) . ?
C7 C4 1.388(2) . ?
C7 C6 1.396(2) . ?
C2 C3 1.386(2) . ?
C2 C5 1.395(2) . ?
C6 C5 1.378(2) . ?
C6 H6 0.939(18) . ?
C10 N3 1.143(2) . ?
C12 C11 1.516(2) . ?
C12 H12A 1.007(12) . ?
C12 H12B 1.007(12) . ?
C12 H12C 1.007(12) . ?
C5 H5 0.979(18) . ?
C3 C4 1.392(2) . ?
C3 H3 0.939(18) . ?
C4 H4 0.929(18) . ?
C11 H11A 0.961(13) . ?
C11 H11B 0.961(13) . ?
C13 C14 1.520(2) . ?
C13 H13A 0.976(13) . ?
C13 H13B 0.976(12) . ?
C1 H1A 0.978(10) . ?
C1 H1B 0.978(11) . ?
C1 H1C 0.978(11) . ?
C14 H14A 0.978(11) . ?
C14 H14B 0.978(11) . ?
C14 H14C 0.978(12) . ?

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
O3 S1 O2 117.41(7) . . ?
O3 S1 N2 113.79(7) . . ?
O2 S1 N2 112.42(7) . . ?
O3 S1 C8 113.43(6) . . ?
O2 S1 C8 113.36(7) . . ?
N2 S1 C8 81.10(6) . . ?
O3 S1 C9 124.68(6) . . ?
O2 S1 C9 117.80(6) . . ?
N2 S1 C9 37.68(6) . . ?
C8 S1 C9 43.59(6) . . ?
C9 N1 C13 122.40(12) . . ?
C9 N1 C11 119.80(12) . . ?
C13 N1 C11 117.73(12) . . ?
C2 O1 C1 116.84(12) . . ?
C10 C8 C7 113.69(12) . . ?
C10 C8 C9 115.53(12) . . ?
C7 C8 C9 115.92(12) . . ?
C10 C8 S1 113.95(10) . . ?
C7 C8 S1 114.39(9) . . ?
C9 C8 S1 78.99(8) . . ?
C9 N2 S1 93.34(10) . . ?
C4 C7 C6 119.10(13) . . ?
C4 C7 C8 120.16(13) . . ?
C6 C7 C8 120.60(13) . . ?
O1 C2 C3 124.47(13) . . ?
O1 C2 C5 115.65(13) . . ?
C3 C2 C5 119.88(13) . . ?
C5 C6 C7 120.47(14) . . ?
C5 C6 H6 119.8 . . ?
C7 C6 H6 119.8 . . ?
N1 C9 N2 127.13(13) . . ?
N1 C9 C8 126.69(13) . . ?
N2 C9 C8 106.13(12) . . ?
N1 C9 S1 175.19(11) . . ?
N2 C9 S1 48.98(7) . . ?
C8 C9 S1 57.42(7) . . ?
N3 C10 C8 179.04(17) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C6 C5 C2 120.13(13) . . ?
C6 C5 H5 119.9 . . ?
C2 C5 H5 119.9 . . ?
C2 C3 C4 119.67(14) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C7 C4 C3 120.71(14) . . ?
C7 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
N1 C11 C12 111.32(12) . . ?
N1 C11 H11A 109.4 . . ?
C12 C11 H11A 109.4 . . ?
N1 C11 H11B 109.4 . . ?
C12 C11 H11B 109.4 . . ?
H11A C11 H11B 108.0 . . ?
N1 C13 C14 111.33(12) . . ?
N1 C13 H13A 109.4 . . ?
C14 C13 H13A 109.4 . . ?
N1 C13 H13B 109.4 . . ?
C14 C13 H13B 109.4 . . ?
H13A C13 H13B 108.0 . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

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
O3 S1 C8 C10 -130.42(11) . . . . ?
O2 S1 C8 C10 6.77(13) . . . . ?
N2 S1 C8 C10 117.43(11) . . . . ?
C9 S1 C8 C10 113.21(13) . . . . ?
O3 S1 C8 C7 2.75(13) . . . . ?
O2 S1 C8 C7 139.94(10) . . . . ?
N2 S1 C8 C7 -109.40(11) . . . . ?
C9 S1 C8 C7 -113.62(13) . . . . ?
O3 S1 C8 C9 116.38(9) . . . . ?
O2 S1 C8 C9 -106.44(9) . . . . ?
N2 S1 C8 C9 4.22(8) . . . . ?
O3 S1 N2 C9 -116.53(10) . . . . ?
O2 S1 N2 C9 106.92(10) . . . . ?
C8 S1 N2 C9 -4.77(9) . . . . ?
C10 C8 C7 C4 29.71(18) . . . . ?
C9 C8 C7 C4 167.15(13) . . . . ?
S1 C8 C7 C4 -103.58(14) . . . . ?
C10 C8 C7 C6 -154.57(13) . . . . ?
C9 C8 C7 C6 -17.13(19) . . . . ?
S1 C8 C7 C6 72.14(15) . . . . ?
C1 O1 C2 C3 5.4(2) . . . . ?
C1 O1 C2 C5 -174.27(13) . . . . ?
C4 C7 C6 C5 0.4(2) . . . . ?
C8 C7 C6 C5 -175.42(13) . . . . ?
C13 N1 C9 N2 171.37(14) . . . . ?
C11 N1 C9 N2 -5.5(2) . . . . ?
C13 N1 C9 C8 -11.4(2) . . . . ?
C11 N1 C9 C8 171.73(13) . . . . ?
S1 N2 C9 N1 -176.35(14) . . . . ?
S1 N2 C9 C8 5.99(12) . . . . ?
C10 C8 C9 N1 65.54(19) . . . . ?
C7 C8 C9 N1 -71.12(18) . . . . ?
S1 C8 C9 N1 176.96(15) . . . . ?
C10 C8 C9 N2 -116.79(14) . . . . ?
C7 C8 C9 N2 106.55(14) . . . . ?
S1 C8 C9 N2 -5.37(10) . . . . ?
C10 C8 C9 S1 -111.43(12) . . . . ?
C7 C8 C9 S1 111.92(12) . . . . ?
C7 C6 C5 C2 1.0(2) . . . . ?
O1 C2 C5 C6 177.42(13) . . . . ?
C3 C2 C5 C6 -2.2(2) . . . . ?
O1 C2 C3 C4 -177.57(14) . . . . ?
C5 C2 C3 C4 2.0(2) . . . . ?
C6 C7 C4 C3 -0.5(2) . . . . ?
C8 C7 C4 C3 175.27(13) . . . . ?
C2 C3 C4 C7 -0.7(2) . . . . ?
C9 N1 C11 C12 -83.61(17) . . . . ?
C13 N1 C11 C12 99.42(15) . . . . ?
C9 N1 C13 C14 -96.09(17) . . . . ?
C11 N1 C13 C14 80.80(16) . . . . ?

_refine_diff_density_max         0.272
_refine_diff_density_min         -0.410
_refine_diff_density_rms         0.048



_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: water'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_B_140
_database_code_depnum_ccdc_archive 'CCDC 1821391'
_audit_update_record             
;
2018-02-02 deposited with the CCDC.
2018-11-08 downloaded from the CCDC.
;
_audit_creation_date             2016-04-18
_audit_creation_method           SHELXL-2016/6
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.5
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
#------------------ CHEMICAL INFORMATION ------------------------------------# 
_chemical_name_systematic        
3-Diethylamino-4-(4-methoxyphenyl)-1,1-dioxo-4H-1λ⁶,2-thiazete-4-carbonitrile
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H17 N3 O3 S'
_chemical_formula_sum            'C14 H17 N3 O3 S'
_chemical_formula_weight         307.36

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.29460(10)
_cell_length_b                   17.2836(3)
_cell_length_c                   10.4035(2)
_cell_angle_alpha                90
_cell_angle_beta                 94.9878(7)
_cell_angle_gamma                90
_cell_volume                     1485.80(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    140(2)
_cell_measurement_reflns_used    6546
_cell_measurement_theta_min      2.2915
_cell_measurement_theta_max      27.5245

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.374
_exptl_crystal_F_000             648
_exptl_transmission_factor_min   0.8753
_exptl_transmission_factor_max   0.9459
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.175
_exptl_crystal_size_min          0.15
_exptl_absorpt_coefficient_mu    0.231
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.8753
_exptl_absorpt_correction_T_max  0.9459
_exptl_absorpt_process_details   'SADABS-2007/4, Bruker'
_diffrn_ambient_temperature      140(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed X-ray tube'
_diffrn_measurement_device_type  'Bruker AXS Smart APEX'
_diffrn_measurement_method       ω-scan
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22216
_diffrn_reflns_av_unetI/netI     0.0195
_diffrn_reflns_av_R_equivalents  0.0296
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.291
_diffrn_reflns_theta_max         27.534
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3427
_reflns_number_gt                2813
_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       'Saint+(Bruker, 2007/4)'
_computing_cell_refinement       'Saint+(Bruker, 2007/4)'
_computing_data_reduction        'Saint+(Bruker, 2007/4)'
_computing_structure_solution    'SHELXS-2016 (Sheldrick, 2016)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.0494P)²+0.7841P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   direct
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3427
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0466
_refine_ls_R_factor_gt           0.0366
_refine_ls_wR_factor_ref         0.0999
_refine_ls_wR_factor_gt          0.0927
_refine_ls_goodness_of_fit_ref   0.990
_refine_ls_restrained_S_all      0.990
_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 0.96962(4) 0.80150(2) 0.39822(4) 0.02787(12) Uani 1 1 d . . . . .
O2 O 1.07997(14) 0.80676(7) 0.51183(11) 0.0365(3) Uani 1 1 d . . . . .
O3 O 1.03734(14) 0.79136(7) 0.27764(12) 0.0354(3) Uani 1 1 d . . . . .
N1 N 0.55796(15) 0.79789(7) 0.44380(12) 0.0246(3) Uani 1 1 d . . . . .
O1 O 0.68009(14) 0.99474(6) -0.11253(10) 0.0313(3) Uani 1 1 d . . . . .
C8 C 0.80394(16) 0.87577(8) 0.39226(14) 0.0225(3) Uani 1 1 d . . . . .
N2 N 0.81525(16) 0.74367(8) 0.41801(13) 0.0307(3) Uani 1 1 d . . . . .
C7 C 0.76232(17) 0.91089(8) 0.26040(13) 0.0221(3) Uani 1 1 d . . . . .
C2 C 0.70834(18) 0.97148(8) 0.01226(13) 0.0237(3) Uani 1 1 d . . . . .
C6 C 0.67961(18) 0.86760(9) 0.16204(14) 0.0252(3) Uani 1 1 d . . . . .
H6 H 0.6428(8) 0.8176(10) 0.1795(4) 0.030 Uiso 1 1 calc R U . . .
C9 C 0.71072(18) 0.80217(8) 0.42270(14) 0.0239(3) Uani 1 1 d . . . . .
C10 C 0.82329(17) 0.93272(9) 0.49579(14) 0.0257(3) Uani 1 1 d . . . . .
C12 C 0.4250(2) 0.68901(10) 0.32247(17) 0.0365(4) Uani 1 1 d . . . . .
H12A H 0.3731(7) 0.6368(6) 0.3327(2) 0.055 Uiso 1 1 calc R U . . .
H12B H 0.3436(10) 0.7255(4) 0.2771(6) 0.055 Uiso 1 1 calc R U . . .
H12C H 0.5209(12) 0.68332(13) 0.2697(7) 0.055 Uiso 1 1 calc R U . . .
C5 C 0.65183(19) 0.89787(9) 0.03970(14) 0.0265(3) Uani 1 1 d . . . . .
H5 H 0.5926(11) 0.8678(6) -0.0278(13) 0.032 Uiso 1 1 calc R U . . .
C3 C 0.78747(19) 1.01555(9) 0.10949(14) 0.0271(3) Uani 1 1 d . . . . .
H3 H 0.8222(7) 1.0658(10) 0.0922(4) 0.033 Uiso 1 1 calc R U . . .
C4 C 0.81495(18) 0.98469(9) 0.23297(14) 0.0257(3) Uani 1 1 d . . . . .
H4 H 0.8699(11) 1.0143(6) 0.2986(13) 0.031 Uiso 1 1 calc R U . . .
C11 C 0.4810(2) 0.72122(9) 0.45427(15) 0.0302(3) Uani 1 1 d . . . . .
H11A H 0.3895(13) 0.72580(11) 0.5050(7) 0.036 Uiso 1 1 calc R U . . .
H11B H 0.5574(11) 0.6859(5) 0.4980(6) 0.036 Uiso 1 1 calc R U . . .
C13 C 0.45936(18) 0.86698(9) 0.46456(15) 0.0287(3) Uani 1 1 d . . . . .
H13A H 0.3494(14) 0.85916(13) 0.4236(6) 0.034 Uiso 1 1 calc R U . . .
H13B H 0.5063(6) 0.9119(6) 0.4236(6) 0.034 Uiso 1 1 calc R U . . .
N3 N 0.83678(18) 0.97791(9) 0.57629(13) 0.0373(3) Uani 1 1 d . . . . .
C1 C 0.7498(2) 1.06678(9) -0.14627(15) 0.0329(4) Uani 1 1 d . . . . .
H1A H 0.7213(4) 1.07735(16) -0.2380(10) 0.049 Uiso 1 1 calc R U . . .
H1B H 0.7080(5) 1.1083(5) -0.0944(6) 0.049 Uiso 1 1 calc R U . . .
H1C H 0.8677(13) 1.06404(10) -0.1296(2) 0.049 Uiso 1 1 calc R U . . .
C14 C 0.4511(2) 0.88323(11) 0.60736(17) 0.0383(4) Uani 1 1 d . . . . .
H14A H 0.3846(8) 0.9296(6) 0.6180(2) 0.058 Uiso 1 1 calc R U . . .
H14B H 0.4023(6) 0.8386(5) 0.6483(5) 0.058 Uiso 1 1 calc R U . . .
H14C H 0.5611(13) 0.89200(15) 0.6484(5) 0.058 Uiso 1 1 calc R U . . .


_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 O3 1.4291(12) . ?
S1 O2 1.4335(12) . ?
S1 N2 1.6513(14) . ?
S1 C8 1.8776(15) . ?
S1 C9 2.1845(15) . ?
N1 C9 1.3067(19) . ?
N1 C13 1.4739(19) . ?
N1 C11 1.4788(19) . ?
O1 C2 1.3598(17) . ?
O1 C1 1.4292(19) . ?
C8 C10 1.458(2) . ?
C8 C7 1.5124(19) . ?
C8 C9 1.536(2) . ?
N2 C9 1.3356(19) . ?
C7 C4 1.386(2) . ?
C7 C6 1.398(2) . ?
C2 C3 1.385(2) . ?
C2 C5 1.394(2) . ?
C6 C5 1.377(2) . ?
C6 H6 0.940(18) . ?
C10 N3 1.143(2) . ?
C12 C11 1.515(2) . ?
C12 H12A 1.010(12) . ?
C12 H12B 1.010(12) . ?
C12 H12C 1.010(12) . ?
C5 H5 0.972(18) . ?
C3 C4 1.391(2) . ?
C3 H3 0.937(19) . ?
C4 H4 0.939(18) . ?
C11 H11A 0.965(13) . ?
C11 H11B 0.965(13) . ?
C13 C14 1.519(2) . ?
C13 H13A 0.982(13) . ?
C13 H13B 0.982(13) . ?
C1 H1A 0.980(11) . ?
C1 H1B 0.980(11) . ?
C1 H1C 0.980(11) . ?
C14 H14A 0.984(12) . ?
C14 H14B 0.984(12) . ?
C14 H14C 0.984(12) . ?

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
O3 S1 O2 117.39(7) . . ?
O3 S1 N2 113.80(7) . . ?
O2 S1 N2 112.46(7) . . ?
O3 S1 C8 113.40(7) . . ?
O2 S1 C8 113.38(7) . . ?
N2 S1 C8 81.06(6) . . ?
O3 S1 C9 124.64(7) . . ?
O2 S1 C9 117.86(6) . . ?
N2 S1 C9 37.61(6) . . ?
C8 S1 C9 43.62(6) . . ?
C9 N1 C13 122.50(13) . . ?
C9 N1 C11 119.60(13) . . ?
C13 N1 C11 117.82(12) . . ?
C2 O1 C1 116.89(12) . . ?
C10 C8 C7 113.64(12) . . ?
C10 C8 C9 115.59(12) . . ?
C7 C8 C9 116.12(12) . . ?
C10 C8 S1 113.83(10) . . ?
C7 C8 S1 114.40(10) . . ?
C9 C8 S1 78.88(8) . . ?
C9 N2 S1 93.40(10) . . ?
C4 C7 C6 119.02(13) . . ?
C4 C7 C8 120.34(13) . . ?
C6 C7 C8 120.51(13) . . ?
O1 C2 C3 124.47(13) . . ?
O1 C2 C5 115.61(13) . . ?
C3 C2 C5 119.92(13) . . ?
C5 C6 C7 120.34(14) . . ?
C5 C6 H6 119.8 . . ?
C7 C6 H6 119.8 . . ?
N1 C9 N2 127.25(14) . . ?
N1 C9 C8 126.47(13) . . ?
N2 C9 C8 106.22(12) . . ?
N1 C9 S1 175.36(11) . . ?
N2 C9 S1 48.99(8) . . ?
C8 C9 S1 57.50(7) . . ?
N3 C10 C8 179.12(17) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C6 C5 C2 120.26(14) . . ?
C6 C5 H5 119.9 . . ?
C2 C5 H5 119.9 . . ?
C2 C3 C4 119.51(14) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C7 C4 C3 120.91(14) . . ?
C7 C4 H4 119.5 . . ?
C3 C4 H4 119.5 . . ?
N1 C11 C12 111.29(13) . . ?
N1 C11 H11A 109.4 . . ?
C12 C11 H11A 109.4 . . ?
N1 C11 H11B 109.4 . . ?
C12 C11 H11B 109.4 . . ?
H11A C11 H11B 108.0 . . ?
N1 C13 C14 111.45(13) . . ?
N1 C13 H13A 109.3 . . ?
C14 C13 H13A 109.3 . . ?
N1 C13 H13B 109.3 . . ?
C14 C13 H13B 109.3 . . ?
H13A C13 H13B 108.0 . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

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
O3 S1 C8 C10 -130.43(11) . . . . ?
O2 S1 C8 C10 6.73(13) . . . . ?
N2 S1 C8 C10 117.42(11) . . . . ?
C9 S1 C8 C10 113.23(13) . . . . ?
O3 S1 C8 C7 2.54(13) . . . . ?
O2 S1 C8 C7 139.70(11) . . . . ?
N2 S1 C8 C7 -109.61(11) . . . . ?
C9 S1 C8 C7 -113.79(14) . . . . ?
O3 S1 C8 C9 116.33(9) . . . . ?
O2 S1 C8 C9 -106.51(9) . . . . ?
N2 S1 C8 C9 4.18(8) . . . . ?
O3 S1 N2 C9 -116.45(10) . . . . ?
O2 S1 N2 C9 106.97(10) . . . . ?
C8 S1 N2 C9 -4.73(9) . . . . ?
C10 C8 C7 C4 29.47(19) . . . . ?
C9 C8 C7 C4 167.18(13) . . . . ?
S1 C8 C7 C4 -103.59(14) . . . . ?
C10 C8 C7 C6 -154.77(13) . . . . ?
C9 C8 C7 C6 -17.06(19) . . . . ?
S1 C8 C7 C6 72.17(15) . . . . ?
C1 O1 C2 C3 5.7(2) . . . . ?
C1 O1 C2 C5 -174.28(14) . . . . ?
C4 C7 C6 C5 0.3(2) . . . . ?
C8 C7 C6 C5 -175.47(13) . . . . ?
C13 N1 C9 N2 171.39(14) . . . . ?
C11 N1 C9 N2 -5.4(2) . . . . ?
C13 N1 C9 C8 -11.5(2) . . . . ?
C11 N1 C9 C8 171.70(13) . . . . ?
S1 N2 C9 N1 -176.50(14) . . . . ?
S1 N2 C9 C8 5.95(12) . . . . ?
C10 C8 C9 N1 65.9(2) . . . . ?
C7 C8 C9 N1 -71.03(19) . . . . ?
S1 C8 C9 N1 177.10(15) . . . . ?
C10 C8 C9 N2 -116.58(14) . . . . ?
C7 C8 C9 N2 106.54(14) . . . . ?
S1 C8 C9 N2 -5.33(11) . . . . ?
C10 C8 C9 S1 -111.25(12) . . . . ?
C7 C8 C9 S1 111.87(12) . . . . ?
C7 C6 C5 C2 1.1(2) . . . . ?
O1 C2 C5 C6 177.52(13) . . . . ?
C3 C2 C5 C6 -2.4(2) . . . . ?
O1 C2 C3 C4 -177.64(14) . . . . ?
C5 C2 C3 C4 2.3(2) . . . . ?
C6 C7 C4 C3 -0.4(2) . . . . ?
C8 C7 C4 C3 175.37(14) . . . . ?
C2 C3 C4 C7 -0.9(2) . . . . ?
C9 N1 C11 C12 -83.98(18) . . . . ?
C13 N1 C11 C12 99.11(16) . . . . ?
C9 N1 C13 C14 -96.14(17) . . . . ?
C11 N1 C13 C14 80.67(17) . . . . ?

_refine_diff_density_max         0.251
_refine_diff_density_min         -0.405
_refine_diff_density_rms         0.047



_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: water'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_B_180
_database_code_depnum_ccdc_archive 'CCDC 1821392'
_audit_update_record             
;
2018-02-02 deposited with the CCDC.
2018-11-08 downloaded from the CCDC.
;
_audit_creation_date             2016-04-18
_audit_creation_method           SHELXL-2016/6
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.5
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
#------------------ CHEMICAL INFORMATION ------------------------------------# 
_chemical_name_systematic        
3-Diethylamino-4-(4-methoxyphenyl)-1,1-dioxo-4H-1λ⁶,2-thiazete-4-carbonitrile
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H17 N3 O3 S'
_chemical_formula_sum            'C14 H17 N3 O3 S'
_chemical_formula_weight         307.36

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.31440(10)
_cell_length_b                   17.3484(3)
_cell_length_c                   10.4141(2)
_cell_angle_alpha                90
_cell_angle_beta                 94.9784(7)
_cell_angle_gamma                90
_cell_volume                     1496.48(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    180(2)
_cell_measurement_reflns_used    5924
_cell_measurement_theta_min      2.2875
_cell_measurement_theta_max      26.506

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.364
_exptl_crystal_F_000             648
_exptl_transmission_factor_min   0.8826
_exptl_transmission_factor_max   0.9459
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.175
_exptl_crystal_size_min          0.15
_exptl_absorpt_coefficient_mu    0.230
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.8826
_exptl_absorpt_correction_T_max  0.9459
_exptl_absorpt_process_details   'SADABS-2007/4, Bruker'
_diffrn_ambient_temperature      180(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed X-ray tube'
_diffrn_measurement_device_type  'Bruker AXS Smart APEX'
_diffrn_measurement_method       ω-scan
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22359
_diffrn_reflns_av_unetI/netI     0.0201
_diffrn_reflns_av_R_equivalents  0.0295
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.287
_diffrn_reflns_theta_max         27.572
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3462
_reflns_number_gt                2743
_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       'Saint+(Bruker, 2007/4)'
_computing_cell_refinement       'Saint+(Bruker, 2007/4)'
_computing_data_reduction        'Saint+(Bruker, 2007/4)'
_computing_structure_solution    'SHELXS-2016 (Sheldrick, 2016)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.0557P)²+0.5620P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   direct
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3462
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0504
_refine_ls_R_factor_gt           0.0373
_refine_ls_wR_factor_ref         0.1078
_refine_ls_wR_factor_gt          0.0984
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_restrained_S_all      1.004
_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 0.96918(5) 0.80148(2) 0.39813(4) 0.03482(13) Uani 1 1 d . . . . .
O2 O 1.07917(14) 0.80666(8) 0.51129(12) 0.0461(3) Uani 1 1 d . . . . .
O3 O 1.03660(15) 0.79134(7) 0.27768(12) 0.0445(3) Uani 1 1 d . . . . .
N1 N 0.55857(15) 0.79788(7) 0.44356(12) 0.0303(3) Uani 1 1 d . . . . .
O1 O 0.68066(15) 0.99435(7) -0.11180(10) 0.0392(3) Uani 1 1 d . . . . .
C8 C 0.80421(17) 0.87557(9) 0.39211(14) 0.0278(3) Uani 1 1 d . . . . .
N2 N 0.81514(17) 0.74401(8) 0.41812(14) 0.0383(3) Uani 1 1 d . . . . .
C7 C 0.76250(17) 0.91050(9) 0.26058(14) 0.0272(3) Uani 1 1 d . . . . .
C2 C 0.70875(18) 0.97111(9) 0.01283(14) 0.0297(3) Uani 1 1 d . . . . .
C6 C 0.68076(19) 0.86757(9) 0.16212(15) 0.0312(3) Uani 1 1 d . . . . .
H6 H 0.6444(8) 0.8178(10) 0.1793(4) 0.037 Uiso 1 1 calc R U . . .
C9 C 0.71092(18) 0.80229(9) 0.42260(14) 0.0293(3) Uani 1 1 d . . . . .
C10 C 0.82335(18) 0.93209(9) 0.49575(15) 0.0322(3) Uani 1 1 d . . . . .
C12 C 0.4257(2) 0.68945(11) 0.32269(18) 0.0460(4) Uani 1 1 d . . . . .
H12A H 0.3736(7) 0.6370(7) 0.3333(2) 0.069 Uiso 1 1 calc R U . . .
H12B H 0.3438(11) 0.7260(5) 0.2771(6) 0.069 Uiso 1 1 calc R U . . .
H12C H 0.5220(12) 0.68365(14) 0.2694(7) 0.069 Uiso 1 1 calc R U . . .
C5 C 0.65312(19) 0.89775(9) 0.04005(15) 0.0330(3) Uani 1 1 d . . . . .
H5 H 0.5945(11) 0.8677(6) -0.0275(13) 0.040 Uiso 1 1 calc R U . . .
C3 C 0.7871(2) 1.01480(9) 0.11005(15) 0.0333(3) Uani 1 1 d . . . . .
H3 H 0.8225(7) 1.0662(10) 0.0925(4) 0.040 Uiso 1 1 calc R U . . .
C4 C 0.81457(19) 0.98418(9) 0.23350(15) 0.0319(3) Uani 1 1 d . . . . .
H4 H 0.8692(11) 1.0139(6) 0.2995(13) 0.038 Uiso 1 1 calc R U . . .
C11 C 0.4819(2) 0.72164(10) 0.45387(16) 0.0378(4) Uani 1 1 d . . . . .
H11A H 0.3915(13) 0.72619(11) 0.5043(8) 0.045 Uiso 1 1 calc R U . . .
H11B H 0.5574(11) 0.6868(5) 0.4972(7) 0.045 Uiso 1 1 calc R U . . .
C13 C 0.46008(19) 0.86670(10) 0.46379(16) 0.0353(4) Uani 1 1 d . . . . .
H13A H 0.3516(15) 0.85897(13) 0.4227(6) 0.042 Uiso 1 1 calc R U . . .
H13B H 0.5068(6) 0.9110(6) 0.4234(6) 0.042 Uiso 1 1 calc R U . . .
N3 N 0.83700(19) 0.97689(10) 0.57647(14) 0.0466(4) Uani 1 1 d . . . . .
C1 C 0.7497(2) 1.06631(10) -0.14559(16) 0.0422(4) Uani 1 1 d . . . . .
H1A H 0.7214(4) 1.07670(17) -0.2367(11) 0.063 Uiso 1 1 calc R U . . .
H1B H 0.7079(5) 1.1074(5) -0.0941(6) 0.063 Uiso 1 1 calc R U . . .
H1C H 0.8666(14) 1.06382(10) -0.1290(3) 0.063 Uiso 1 1 calc R U . . .
C14 C 0.4507(2) 0.88298(12) 0.60615(18) 0.0482(5) Uani 1 1 d . . . . .
H14A H 0.3846(9) 0.9289(6) 0.6163(2) 0.072 Uiso 1 1 calc R U . . .
H14B H 0.4019(6) 0.8388(6) 0.6466(6) 0.072 Uiso 1 1 calc R U . . .
H14C H 0.5596(14) 0.89169(16) 0.6474(6) 0.072 Uiso 1 1 calc R U . . .


_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 O3 1.4285(13) . ?
S1 O2 1.4305(13) . ?
S1 N2 1.6504(15) . ?
S1 C8 1.8768(15) . ?
S1 C9 2.1842(16) . ?
N1 C9 1.306(2) . ?
N1 C13 1.473(2) . ?
N1 C11 1.476(2) . ?
O1 C2 1.3598(18) . ?
O1 C1 1.431(2) . ?
C8 C10 1.457(2) . ?
C8 C7 1.510(2) . ?
C8 C9 1.537(2) . ?
N2 C9 1.335(2) . ?
C7 C4 1.386(2) . ?
C7 C6 1.395(2) . ?
C2 C3 1.382(2) . ?
C2 C5 1.392(2) . ?
C6 C5 1.376(2) . ?
C6 H6 0.937(19) . ?
C10 N3 1.143(2) . ?
C12 C11 1.512(3) . ?
C12 H12A 1.018(13) . ?
C12 H12B 1.018(13) . ?
C12 H12C 1.018(13) . ?
C5 H5 0.972(18) . ?
C3 C4 1.392(2) . ?
C3 H3 0.962(19) . ?
C4 H4 0.944(18) . ?
C11 H11A 0.956(14) . ?
C11 H11B 0.956(14) . ?
C13 C14 1.518(2) . ?
C13 H13A 0.974(13) . ?
C13 H13B 0.974(13) . ?
C1 H1A 0.974(11) . ?
C1 H1B 0.974(11) . ?
C1 H1C 0.974(11) . ?
C14 H14A 0.979(12) . ?
C14 H14B 0.979(12) . ?
C14 H14C 0.979(12) . ?

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
O3 S1 O2 117.36(8) . . ?
O3 S1 N2 113.85(8) . . ?
O2 S1 N2 112.44(8) . . ?
O3 S1 C8 113.35(7) . . ?
O2 S1 C8 113.43(7) . . ?
N2 S1 C8 81.09(7) . . ?
O3 S1 C9 124.61(7) . . ?
O2 S1 C9 117.91(7) . . ?
N2 S1 C9 37.60(6) . . ?
C8 S1 C9 43.65(6) . . ?
C9 N1 C13 122.38(13) . . ?
C9 N1 C11 119.74(13) . . ?
C13 N1 C11 117.81(13) . . ?
C2 O1 C1 117.01(13) . . ?
C10 C8 C7 113.80(13) . . ?
C10 C8 C9 115.37(12) . . ?
C7 C8 C9 116.04(13) . . ?
C10 C8 S1 113.81(11) . . ?
C7 C8 S1 114.50(10) . . ?
C9 C8 S1 78.88(9) . . ?
C9 N2 S1 93.44(10) . . ?
C4 C7 C6 118.91(14) . . ?
C4 C7 C8 120.22(14) . . ?
C6 C7 C8 120.74(14) . . ?
O1 C2 C3 124.59(14) . . ?
O1 C2 C5 115.66(14) . . ?
C3 C2 C5 119.75(14) . . ?
C5 C6 C7 120.50(15) . . ?
C5 C6 H6 119.7 . . ?
C7 C6 H6 119.7 . . ?
N1 C9 N2 127.10(14) . . ?
N1 C9 C8 126.68(13) . . ?
N2 C9 C8 106.17(13) . . ?
N1 C9 S1 175.26(12) . . ?
N2 C9 S1 48.96(8) . . ?
C8 C9 S1 57.47(7) . . ?
N3 C10 C8 179.26(18) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C6 C5 C2 120.30(15) . . ?
C6 C5 H5 119.9 . . ?
C2 C5 H5 119.9 . . ?
C2 C3 C4 119.78(15) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C7 C4 C3 120.72(15) . . ?
C7 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
N1 C11 C12 111.51(14) . . ?
N1 C11 H11A 109.3 . . ?
C12 C11 H11A 109.3 . . ?
N1 C11 H11B 109.3 . . ?
C12 C11 H11B 109.3 . . ?
H11A C11 H11B 108.0 . . ?
N1 C13 C14 111.51(13) . . ?
N1 C13 H13A 109.3 . . ?
C14 C13 H13A 109.3 . . ?
N1 C13 H13B 109.3 . . ?
C14 C13 H13B 109.3 . . ?
H13A C13 H13B 108.0 . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

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
O3 S1 C8 C10 -130.68(11) . . . . ?
O2 S1 C8 C10 6.43(13) . . . . ?
N2 S1 C8 C10 117.10(12) . . . . ?
C9 S1 C8 C10 112.98(14) . . . . ?
O3 S1 C8 C7 2.63(14) . . . . ?
O2 S1 C8 C7 139.73(11) . . . . ?
N2 S1 C8 C7 -109.59(12) . . . . ?
C9 S1 C8 C7 -113.71(14) . . . . ?
O3 S1 C8 C9 116.34(10) . . . . ?
O2 S1 C8 C9 -106.56(10) . . . . ?
N2 S1 C8 C9 4.12(9) . . . . ?
O3 S1 N2 C9 -116.34(10) . . . . ?
O2 S1 N2 C9 107.09(11) . . . . ?
C8 S1 N2 C9 -4.66(10) . . . . ?
C10 C8 C7 C4 29.37(19) . . . . ?
C9 C8 C7 C4 166.83(13) . . . . ?
S1 C8 C7 C4 -103.94(15) . . . . ?
C10 C8 C7 C6 -154.94(14) . . . . ?
C9 C8 C7 C6 -17.5(2) . . . . ?
S1 C8 C7 C6 71.74(16) . . . . ?
C1 O1 C2 C3 5.6(2) . . . . ?
C1 O1 C2 C5 -174.21(15) . . . . ?
C4 C7 C6 C5 0.4(2) . . . . ?
C8 C7 C6 C5 -175.38(14) . . . . ?
C13 N1 C9 N2 171.55(15) . . . . ?
C11 N1 C9 N2 -5.5(2) . . . . ?
C13 N1 C9 C8 -11.4(2) . . . . ?
C11 N1 C9 C8 171.59(14) . . . . ?
S1 N2 C9 N1 -176.61(15) . . . . ?
S1 N2 C9 C8 5.86(12) . . . . ?
C10 C8 C9 N1 66.0(2) . . . . ?
C7 C8 C9 N1 -70.8(2) . . . . ?
S1 C8 C9 N1 177.21(15) . . . . ?
C10 C8 C9 N2 -116.47(15) . . . . ?
C7 C8 C9 N2 106.74(15) . . . . ?
S1 C8 C9 N2 -5.24(11) . . . . ?
C10 C8 C9 S1 -111.23(13) . . . . ?
C7 C8 C9 S1 111.98(13) . . . . ?
C7 C6 C5 C2 1.0(2) . . . . ?
O1 C2 C5 C6 177.54(14) . . . . ?
C3 C2 C5 C6 -2.3(2) . . . . ?
O1 C2 C3 C4 -177.67(15) . . . . ?
C5 C2 C3 C4 2.1(2) . . . . ?
C6 C7 C4 C3 -0.5(2) . . . . ?
C8 C7 C4 C3 175.27(14) . . . . ?
C2 C3 C4 C7 -0.8(2) . . . . ?
C9 N1 C11 C12 -84.07(19) . . . . ?
C13 N1 C11 C12 98.79(17) . . . . ?
C9 N1 C13 C14 -96.48(18) . . . . ?
C11 N1 C13 C14 80.58(18) . . . . ?

_refine_diff_density_max         0.229
_refine_diff_density_min         -0.345
_refine_diff_density_rms         0.044



_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: water'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_B_260
_database_code_depnum_ccdc_archive 'CCDC 1821395'
_audit_update_record             
;
2018-02-02 deposited with the CCDC.
2018-11-08 downloaded from the CCDC.
;
_audit_creation_date             2016-04-18
_audit_creation_method           SHELXL-2016/6
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.5
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
#------------------ CHEMICAL INFORMATION ------------------------------------# 
_chemical_name_systematic        
3-Diethylamino-4-(4-methoxyphenyl)-1,1-dioxo-4H-1λ⁶,2-thiazete-4-carbonitrile
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H17 N3 O3 S'
_chemical_formula_sum            'C14 H17 N3 O3 S'
_chemical_formula_weight         307.36

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.3607(2)
_cell_length_b                   17.4896(3)
_cell_length_c                   10.4410(2)
_cell_angle_alpha                90
_cell_angle_beta                 95.0136(8)
_cell_angle_gamma                90
_cell_volume                     1520.90(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    260(2)
_cell_measurement_reflns_used    4956
_cell_measurement_theta_min      2.278
_cell_measurement_theta_max      24.5575

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_F_000             648
_exptl_transmission_factor_min   0.8888
_exptl_transmission_factor_max   0.9459
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.175
_exptl_crystal_size_min          0.15
_exptl_absorpt_coefficient_mu    0.226
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.8888
_exptl_absorpt_correction_T_max  0.9459
_exptl_absorpt_process_details   'SADABS-2007/4, Bruker'
_diffrn_ambient_temperature      260(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed X-ray tube'
_diffrn_measurement_device_type  'Bruker AXS Smart APEX'
_diffrn_measurement_method       ω-scan
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22741
_diffrn_reflns_av_unetI/netI     0.0224
_diffrn_reflns_av_R_equivalents  0.0322
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.278
_diffrn_reflns_theta_max         27.547
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3511
_reflns_number_gt                2548
_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       'Saint+(Bruker, 2007/4)'
_computing_cell_refinement       'Saint+(Bruker, 2007/4)'
_computing_data_reduction        'Saint+(Bruker, 2007/4)'
_computing_structure_solution    'SHELXS-2016 (Sheldrick, 2016)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.0573P)²+0.4580P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   direct
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3511
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0610
_refine_ls_R_factor_gt           0.0407
_refine_ls_wR_factor_ref         0.1182
_refine_ls_wR_factor_gt          0.1046
_refine_ls_goodness_of_fit_ref   0.989
_refine_ls_restrained_S_all      0.989
_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 0.96823(5) 0.80148(3) 0.39823(5) 0.05146(16) Uani 1 1 d . . . . .
O2 O 1.07796(16) 0.80664(10) 0.51056(14) 0.0686(4) Uani 1 1 d . . . . .
O3 O 1.03479(17) 0.79120(9) 0.27834(14) 0.0654(4) Uani 1 1 d . . . . .
N1 N 0.56015(17) 0.79791(8) 0.44282(14) 0.0438(3) Uani 1 1 d . . . . .
O1 O 0.68183(17) 0.99352(8) -0.11004(12) 0.0574(4) Uani 1 1 d . . . . .
C8 C 0.80441(19) 0.87502(10) 0.39187(16) 0.0398(4) Uani 1 1 d . . . . .
N2 N 0.81520(19) 0.74474(10) 0.41854(16) 0.0560(4) Uani 1 1 d . . . . .
C7 C 0.76341(18) 0.90990(9) 0.26096(15) 0.0377(4) Uani 1 1 d . . . . .
C2 C 0.7096(2) 0.97030(10) 0.01432(16) 0.0426(4) Uani 1 1 d . . . . .
C6 C 0.6832(2) 0.86751(10) 0.16221(16) 0.0443(4) Uani 1 1 d . . . . .
H6 H 0.6484(8) 0.8189(11) 0.1785(4) 0.053 Uiso 1 1 calc R U . . .
C9 C 0.7116(2) 0.80252(10) 0.42236(16) 0.0421(4) Uani 1 1 d . . . . .
C10 C 0.8238(2) 0.93096(11) 0.49559(17) 0.0460(4) Uani 1 1 d . . . . .
C12 C 0.4270(3) 0.69043(13) 0.3236(2) 0.0676(6) Uani 1 1 d . . . . .
H12A H 0.3760(8) 0.6387(7) 0.3345(3) 0.101 Uiso 1 1 calc R U . . .
H12B H 0.3454(12) 0.7264(5) 0.2791(7) 0.101 Uiso 1 1 calc R U . . .
H12C H 0.5212(13) 0.68482(16) 0.2699(8) 0.101 Uiso 1 1 calc R U . . .
C5 C 0.6558(2) 0.89758(11) 0.04104(17) 0.0465(4) Uani 1 1 d . . . . .
H5 H 0.5979(12) 0.8676(6) -0.0268(14) 0.056 Uiso 1 1 calc R U . . .
C3 C 0.7862(2) 1.01347(11) 0.11150(17) 0.0484(4) Uani 1 1 d . . . . .
H3 H 0.8197(8) 1.0631(12) 0.0949(4) 0.058 Uiso 1 1 calc R U . . .
C4 C 0.8134(2) 0.98294(10) 0.23418(17) 0.0458(4) Uani 1 1 d . . . . .
H4 H 0.8662(12) 1.0123(6) 0.2996(14) 0.055 Uiso 1 1 calc R U . . .
C11 C 0.4842(2) 0.72215(11) 0.45304(19) 0.0541(5) Uani 1 1 d . . . . .
H11A H 0.3954(14) 0.72647(13) 0.5040(8) 0.065 Uiso 1 1 calc R U . . .
H11B H 0.5598(12) 0.6877(5) 0.4954(7) 0.065 Uiso 1 1 calc R U . . .
C13 C 0.4614(2) 0.86603(11) 0.46195(19) 0.0507(5) Uani 1 1 d . . . . .
H13A H 0.3552(16) 0.85818(15) 0.4208(7) 0.061 Uiso 1 1 calc R U . . .
H13B H 0.5075(7) 0.9095(6) 0.4222(6) 0.061 Uiso 1 1 calc R U . . .
N3 N 0.8381(2) 0.97481(12) 0.57627(16) 0.0671(5) Uani 1 1 d . . . . .
C1 C 0.7496(3) 1.06493(12) -0.14379(19) 0.0623(6) Uani 1 1 d . . . . .
H1A H 0.7213(4) 1.07520(19) -0.2352(12) 0.093 Uiso 1 1 calc R U . . .
H1B H 0.7073(6) 1.1059(6) -0.0922(7) 0.093 Uiso 1 1 calc R U . . .
H1C H 0.8667(15) 1.06273(12) -0.1271(3) 0.093 Uiso 1 1 calc R U . . .
C14 C 0.4504(3) 0.88264(14) 0.6032(2) 0.0695(6) Uani 1 1 d . . . . .
H14A H 0.3846(10) 0.9278(6) 0.6121(3) 0.104 Uiso 1 1 calc R U . . .
H14B H 0.4021(7) 0.8392(6) 0.6433(6) 0.104 Uiso 1 1 calc R U . . .
H14C H 0.5573(15) 0.89154(19) 0.6447(6) 0.104 Uiso 1 1 calc R U . . .


_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 O3 1.4250(15) . ?
S1 O2 1.4274(15) . ?
S1 N2 1.6474(17) . ?
S1 C8 1.8759(17) . ?
S1 C9 2.1820(18) . ?
N1 C9 1.305(2) . ?
N1 C13 1.473(2) . ?
N1 C11 1.477(2) . ?
O1 C2 1.361(2) . ?
O1 C1 1.428(2) . ?
C8 C10 1.458(3) . ?
C8 C7 1.509(2) . ?
C8 C9 1.534(2) . ?
N2 C9 1.334(2) . ?
C7 C4 1.380(2) . ?
C7 C6 1.393(2) . ?
C2 C3 1.377(3) . ?
C2 C5 1.386(2) . ?
C6 C5 1.371(2) . ?
C6 H6 0.92(2) . ?
C10 N3 1.138(2) . ?
C12 C11 1.500(3) . ?
C12 H12A 1.011(14) . ?
C12 H12B 1.011(14) . ?
C12 H12C 1.011(14) . ?
C5 H5 0.98(2) . ?
C3 C4 1.388(2) . ?
C3 H3 0.93(2) . ?
C4 H4 0.93(2) . ?
C11 H11A 0.954(15) . ?
C11 H11B 0.954(15) . ?
C13 C14 1.513(3) . ?
C13 H13A 0.962(14) . ?
C13 H13B 0.962(14) . ?
C1 H1A 0.980(13) . ?
C1 H1B 0.980(13) . ?
C1 H1C 0.980(13) . ?
C14 H14A 0.972(14) . ?
C14 H14B 0.972(14) . ?
C14 H14C 0.972(14) . ?

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
O3 S1 O2 117.23(9) . . ?
O3 S1 N2 113.85(10) . . ?
O2 S1 N2 112.51(9) . . ?
O3 S1 C8 113.29(8) . . ?
O2 S1 C8 113.62(9) . . ?
N2 S1 C8 81.06(8) . . ?
O3 S1 C9 124.46(8) . . ?
O2 S1 C9 118.19(8) . . ?
N2 S1 C9 37.60(7) . . ?
C8 S1 C9 43.62(7) . . ?
C9 N1 C13 122.37(15) . . ?
C9 N1 C11 119.78(15) . . ?
C13 N1 C11 117.81(15) . . ?
C2 O1 C1 117.26(15) . . ?
C10 C8 C7 113.79(15) . . ?
C10 C8 C9 115.20(14) . . ?
C7 C8 C9 116.31(14) . . ?
C10 C8 S1 113.60(12) . . ?
C7 C8 S1 114.63(11) . . ?
C9 C8 S1 78.86(10) . . ?
C9 N2 S1 93.50(12) . . ?
C4 C7 C6 118.50(16) . . ?
C4 C7 C8 120.59(15) . . ?
C6 C7 C8 120.79(15) . . ?
O1 C2 C3 124.68(16) . . ?
O1 C2 C5 115.76(16) . . ?
C3 C2 C5 119.56(16) . . ?
C5 C6 C7 120.65(17) . . ?
C5 C6 H6 119.7 . . ?
C7 C6 H6 119.7 . . ?
N1 C9 N2 126.86(17) . . ?
N1 C9 C8 126.91(15) . . ?
N2 C9 C8 106.18(15) . . ?
N1 C9 S1 175.10(13) . . ?
N2 C9 S1 48.90(9) . . ?
C8 C9 S1 57.51(8) . . ?
N3 C10 C8 179.6(2) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C6 C5 C2 120.45(17) . . ?
C6 C5 H5 119.8 . . ?
C2 C5 H5 119.8 . . ?
C2 C3 C4 119.80(17) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C7 C4 C3 121.00(17) . . ?
C7 C4 H4 119.5 . . ?
C3 C4 H4 119.5 . . ?
N1 C11 C12 111.82(16) . . ?
N1 C11 H11A 109.3 . . ?
C12 C11 H11A 109.3 . . ?
N1 C11 H11B 109.3 . . ?
C12 C11 H11B 109.3 . . ?
H11A C11 H11B 107.9 . . ?
N1 C13 C14 111.72(16) . . ?
N1 C13 H13A 109.3 . . ?
C14 C13 H13A 109.3 . . ?
N1 C13 H13B 109.3 . . ?
C14 C13 H13B 109.3 . . ?
H13A C13 H13B 107.9 . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

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
O3 S1 C8 C10 -131.01(13) . . . . ?
O2 S1 C8 C10 6.03(16) . . . . ?
N2 S1 C8 C10 116.78(14) . . . . ?
C9 S1 C8 C10 112.80(15) . . . . ?
O3 S1 C8 C7 2.19(16) . . . . ?
O2 S1 C8 C7 139.23(13) . . . . ?
N2 S1 C8 C7 -110.02(14) . . . . ?
C9 S1 C8 C7 -114.00(16) . . . . ?
O3 S1 C8 C9 116.19(11) . . . . ?
O2 S1 C8 C9 -106.77(11) . . . . ?
N2 S1 C8 C9 3.98(10) . . . . ?
O3 S1 N2 C9 -116.10(12) . . . . ?
O2 S1 N2 C9 107.45(13) . . . . ?
C8 S1 N2 C9 -4.50(11) . . . . ?
C10 C8 C7 C4 28.5(2) . . . . ?
C9 C8 C7 C4 166.02(15) . . . . ?
S1 C8 C7 C4 -104.57(17) . . . . ?
C10 C8 C7 C6 -155.51(15) . . . . ?
C9 C8 C7 C6 -18.0(2) . . . . ?
S1 C8 C7 C6 71.37(18) . . . . ?
C1 O1 C2 C3 5.8(3) . . . . ?
C1 O1 C2 C5 -173.94(17) . . . . ?
C4 C7 C6 C5 0.5(3) . . . . ?
C8 C7 C6 C5 -175.55(15) . . . . ?
C13 N1 C9 N2 171.77(17) . . . . ?
C11 N1 C9 N2 -5.5(3) . . . . ?
C13 N1 C9 C8 -11.2(3) . . . . ?
C11 N1 C9 C8 171.47(16) . . . . ?
S1 N2 C9 N1 -176.82(17) . . . . ?
S1 N2 C9 C8 5.66(14) . . . . ?
C10 C8 C9 N1 66.4(2) . . . . ?
C7 C8 C9 N1 -70.5(2) . . . . ?
S1 C8 C9 N1 177.43(18) . . . . ?
C10 C8 C9 N2 -116.06(17) . . . . ?
C7 C8 C9 N2 107.06(17) . . . . ?
S1 C8 C9 N2 -5.06(13) . . . . ?
C10 C8 C9 S1 -111.00(14) . . . . ?
C7 C8 C9 S1 112.12(14) . . . . ?
C7 C6 C5 C2 1.0(3) . . . . ?
O1 C2 C5 C6 177.46(16) . . . . ?
C3 C2 C5 C6 -2.3(3) . . . . ?
O1 C2 C3 C4 -177.67(17) . . . . ?
C3 C2 C3 C4 2.1(3) . . . . ?
C6 C7 C4 C3 -0.7(3) . . . . ?
C8 C7 C4 C3 175.34(16) . . . . ?
C2 C3 C4 C7 -0.6(3) . . . . ?
C9 N1 C11 C12 -84.9(2) . . . . ?
C13 N1 C11 C12 97.7(2) . . . . ?
C9 N1 C13 C14 -96.8(2) . . . . ?
C11 N1 C13 C14 80.6(2) . . . . ?

_refine_diff_density_max         0.224
_refine_diff_density_min         -0.328
_refine_diff_density_rms         0.038



_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: water'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_B_220
_database_code_depnum_ccdc_archive 'CCDC 1821394'
_audit_update_record             
;
2018-02-02 deposited with the CCDC.
2018-11-08 downloaded from the CCDC.
;
_audit_creation_date             2016-04-18
_audit_creation_method           SHELXL-2016/6
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.5
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
#------------------ CHEMICAL INFORMATION ------------------------------------# 
_chemical_name_systematic        
3-Diethylamino-4-(4-methoxyphenyl)-1,1-dioxo-4H-1λ⁶,2-thiazete-4-carbonitrile
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H17 N3 O3 S'
_chemical_formula_sum            'C14 H17 N3 O3 S'
_chemical_formula_weight         307.36

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.33650(10)
_cell_length_b                   17.4149(3)
_cell_length_c                   10.4268(2)
_cell_angle_alpha                90
_cell_angle_beta                 94.9907(8)
_cell_angle_gamma                90
_cell_volume                     1508.02(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    220(2)
_cell_measurement_reflns_used    5418
_cell_measurement_theta_min      2.283
_cell_measurement_theta_max      24.637

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_F_000             648
_exptl_transmission_factor_min   0.8794
_exptl_transmission_factor_max   0.9459
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.175
_exptl_crystal_size_min          0.15
_exptl_absorpt_coefficient_mu    0.228
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.8794
_exptl_absorpt_correction_T_max  0.9459
_exptl_absorpt_process_details   'SADABS-2007/4, Bruker'
_diffrn_ambient_temperature      220(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed X-ray tube'
_diffrn_measurement_device_type  'Bruker AXS Smart APEX'
_diffrn_measurement_method       ω-scan
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22543
_diffrn_reflns_av_unetI/netI     0.0210
_diffrn_reflns_av_R_equivalents  0.0304
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.283
_diffrn_reflns_theta_max         27.563
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3489
_reflns_number_gt                2672
_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       'Saint+(Bruker, 2007/4)'
_computing_cell_refinement       'Saint+(Bruker, 2007/4)'
_computing_data_reduction        'Saint+(Bruker, 2007/4)'
_computing_structure_solution    'SHELXS-2016 (Sheldrick, 2016)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.0568P)²+0.5559P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   direct
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3489
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0559
_refine_ls_R_factor_gt           0.0394
_refine_ls_wR_factor_ref         0.1142
_refine_ls_wR_factor_gt          0.1021
_refine_ls_goodness_of_fit_ref   0.993
_refine_ls_restrained_S_all      0.993
_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 0.96865(5) 0.80145(3) 0.39813(4) 0.04256(15) Uani 1 1 d . . . . .
O2 O 1.07867(16) 0.80659(9) 0.51088(13) 0.0565(4) Uani 1 1 d . . . . .
O3 O 1.03561(16) 0.79126(8) 0.27787(14) 0.0542(4) Uani 1 1 d . . . . .
N1 N 0.55905(16) 0.79794(8) 0.44314(13) 0.0366(3) Uani 1 1 d . . . . .
O1 O 0.68136(16) 0.99395(7) -0.11094(11) 0.0476(3) Uani 1 1 d . . . . .
C8 C 0.80433(18) 0.87518(9) 0.39190(15) 0.0334(3) Uani 1 1 d . . . . .
N2 N 0.81524(18) 0.74439(9) 0.41822(15) 0.0464(4) Uani 1 1 d . . . . .
C7 C 0.76301(18) 0.91031(9) 0.26069(15) 0.0319(3) Uani 1 1 d . . . . .
C2 C 0.7094(2) 0.97073(9) 0.01353(15) 0.0357(4) Uani 1 1 d . . . . .
C6 C 0.6819(2) 0.86749(10) 0.16217(16) 0.0374(4) Uani 1 1 d . . . . .
H6 H 0.6462(8) 0.8183(11) 0.1789(4) 0.045 Uiso 1 1 calc R U . . .
C9 C 0.7113(2) 0.80247(9) 0.42246(15) 0.0352(4) Uani 1 1 d . . . . .
C10 C 0.8235(2) 0.93158(10) 0.49560(16) 0.0385(4) Uani 1 1 d . . . . .
C12 C 0.4264(3) 0.68996(12) 0.3230(2) 0.0566(5) Uani 1 1 d . . . . .
H12A H 0.3752(8) 0.6381(7) 0.3336(2) 0.085 Uiso 1 1 calc R U . . .
H12B H 0.3450(11) 0.7260(5) 0.2783(7) 0.085 Uiso 1 1 calc R U . . .
H12C H 0.5212(13) 0.68440(15) 0.2698(8) 0.085 Uiso 1 1 calc R U . . .
C5 C 0.6544(2) 0.89771(10) 0.04055(16) 0.0393(4) Uani 1 1 d . . . . .
H5 H 0.5954(12) 0.8674(6) -0.0278(14) 0.047 Uiso 1 1 calc R U . . .
C3 C 0.7868(2) 1.01424(10) 0.11080(16) 0.0404(4) Uani 1 1 d . . . . .
H3 H 0.8213(8) 1.0649(11) 0.0937(4) 0.048 Uiso 1 1 calc R U . . .
C4 C 0.8140(2) 0.98363(10) 0.23376(16) 0.0384(4) Uani 1 1 d . . . . .
H4 H 0.8674(12) 1.0129(6) 0.2990(14) 0.046 Uiso 1 1 calc R U . . .
C11 C 0.4830(2) 0.72185(11) 0.45347(18) 0.0456(4) Uani 1 1 d . . . . .
H11A H 0.3933(14) 0.72621(12) 0.5042(8) 0.055 Uiso 1 1 calc R U . . .
H11B H 0.5587(12) 0.6872(5) 0.4963(7) 0.055 Uiso 1 1 calc R U . . .
C13 C 0.4606(2) 0.86643(10) 0.46281(18) 0.0427(4) Uani 1 1 d . . . . .
H13A H 0.3532(15) 0.85871(14) 0.4217(6) 0.051 Uiso 1 1 calc R U . . .
H13B H 0.5071(7) 0.9103(6) 0.4228(6) 0.051 Uiso 1 1 calc R U . . .
N3 N 0.8375(2) 0.97585(11) 0.57623(16) 0.0564(4) Uani 1 1 d . . . . .
C1 C 0.7498(3) 1.06555(11) -0.14474(18) 0.0518(5) Uani 1 1 d . . . . .
H1A H 0.7217(4) 1.07582(18) -0.2353(12) 0.078 Uiso 1 1 calc R U . . .
H1B H 0.7083(6) 1.1063(5) -0.0936(7) 0.078 Uiso 1 1 calc R U . . .
H1C H 0.8659(15) 1.06317(11) -0.1283(3) 0.078 Uiso 1 1 calc R U . . .
C14 C 0.4507(3) 0.88262(13) 0.6048(2) 0.0582(5) Uani 1 1 d . . . . .
H14A H 0.3848(9) 0.9282(6) 0.6147(3) 0.087 Uiso 1 1 calc R U . . .
H14B H 0.4021(7) 0.8387(6) 0.6450(6) 0.087 Uiso 1 1 calc R U . . .
H14C H 0.5588(15) 0.89131(18) 0.6462(6) 0.087 Uiso 1 1 calc R U . . .


_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 O3 1.4273(14) . ?
S1 O2 1.4296(14) . ?
S1 N2 1.6473(16) . ?
S1 C8 1.8745(16) . ?
S1 C9 2.1821(17) . ?
N1 C9 1.308(2) . ?
N1 C13 1.472(2) . ?
N1 C11 1.477(2) . ?
O1 C2 1.3601(19) . ?
O1 C1 1.428(2) . ?
C8 C10 1.459(2) . ?
C8 C7 1.511(2) . ?
C8 C9 1.533(2) . ?
N2 C9 1.335(2) . ?
C7 C4 1.382(2) . ?
C7 C6 1.396(2) . ?
C2 C3 1.380(2) . ?
C2 C5 1.389(2) . ?
C6 C5 1.374(2) . ?
C6 H6 0.93(2) . ?
C10 N3 1.139(2) . ?
C12 C11 1.506(3) . ?
C12 H12A 1.009(14) . ?
C12 H12B 1.009(14) . ?
C12 H12C 1.009(14) . ?
C5 H5 0.983(19) . ?
C3 C4 1.389(2) . ?
C3 H3 0.95(2) . ?
C4 H4 0.932(19) . ?
C11 H11A 0.956(14) . ?
C11 H11B 0.956(14) . ?
C13 C14 1.517(3) . ?
C13 H13A 0.968(14) . ?
C13 H13B 0.968(14) . ?
C1 H1A 0.969(12) . ?
C1 H1B 0.969(12) . ?
C1 H1C 0.969(12) . ?
C14 H14A 0.977(13) . ?
C14 H14B 0.977(13) . ?
C14 H14C 0.977(13) . ?

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
O3 S1 O2 117.28(9) . . ?
O3 S1 N2 113.83(9) . . ?
O2 S1 N2 112.51(8) . . ?
O3 S1 C8 113.28(8) . . ?
O2 S1 C8 113.60(8) . . ?
N2 S1 C8 81.06(7) . . ?
O3 S1 C9 124.52(8) . . ?
O2 S1 C9 118.09(8) . . ?
N2 S1 C9 37.64(7) . . ?
C8 S1 C9 43.58(6) . . ?
C9 N1 C13 122.33(14) . . ?
C9 N1 C11 119.68(15) . . ?
C13 N1 C11 117.93(14) . . ?
C2 O1 C1 117.11(14) . . ?
C10 C8 C7 113.58(14) . . ?
C10 C8 C9 115.26(13) . . ?
C7 C8 C9 116.31(13) . . ?
C10 C8 S1 113.75(11) . . ?
C7 C8 S1 114.65(11) . . ?
C9 C8 S1 78.95(9) . . ?
C9 N2 S1 93.46(11) . . ?
C4 C7 C6 118.81(15) . . ?
C4 C7 C8 120.54(15) . . ?
C6 C7 C8 120.52(15) . . ?
O1 C2 C3 124.65(15) . . ?
O1 C2 C5 115.68(15) . . ?
C3 C2 C5 119.67(15) . . ?
C5 C6 C7 120.40(16) . . ?
C5 C6 H6 119.8 . . ?
C7 C6 H6 119.8 . . ?
N1 C9 N2 126.98(16) . . ?
N1 C9 C8 126.85(14) . . ?
N2 C9 C8 106.11(14) . . ?
N1 C9 S1 175.17(13) . . ?
N2 C9 S1 48.90(9) . . ?
C8 C9 S1 57.47(8) . . ?
N3 C10 C8 179.5(2) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C6 C5 C2 120.43(16) . . ?
C6 C5 H5 119.8 . . ?
C2 C5 H5 119.8 . . ?
C2 C3 C4 119.73(16) . . ?
C2 C3 H3 120.1 . . ?
C4 C3 H3 120.1 . . ?
C7 C4 C3 120.91(16) . . ?
C7 C4 H4 119.5 . . ?
C3 C4 H4 119.5 . . ?
N1 C11 C12 111.56(15) . . ?
N1 C11 H11A 109.3 . . ?
C12 C11 H11A 109.3 . . ?
N1 C11 H11B 109.3 . . ?
C12 C11 H11B 109.3 . . ?
H11A C11 H11B 108.0 . . ?
N1 C13 C14 111.41(15) . . ?
N1 C13 H13A 109.3 . . ?
C14 C13 H13A 109.3 . . ?
N1 C13 H13B 109.3 . . ?
C14 C13 H13B 109.3 . . ?
H13A C13 H13B 108.0 . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

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
O3 S1 C8 C10 -130.81(12) . . . . ?
O2 S1 C8 C10 6.27(15) . . . . ?
N2 S1 C8 C10 117.01(13) . . . . ?
C9 S1 C8 C10 112.90(15) . . . . ?
O3 S1 C8 C7 2.26(15) . . . . ?
O2 S1 C8 C7 139.34(12) . . . . ?
N2 S1 C8 C7 -109.92(13) . . . . ?
C9 S1 C8 C7 -114.03(15) . . . . ?
O3 S1 C8 C9 116.29(10) . . . . ?
O2 S1 C8 C9 -106.63(10) . . . . ?
N2 S1 C8 C9 4.11(10) . . . . ?
O3 S1 N2 C9 -116.22(11) . . . . ?
O2 S1 N2 C9 107.29(12) . . . . ?
C8 S1 N2 C9 -4.64(11) . . . . ?
C10 C8 C7 C4 29.0(2) . . . . ?
C9 C8 C7 C4 166.34(14) . . . . ?
S1 C8 C7 C4 -104.14(16) . . . . ?
C10 C8 C7 C6 -155.19(15) . . . . ?
C9 C8 C7 C6 -17.9(2) . . . . ?
S1 C8 C7 C6 71.67(17) . . . . ?
C1 O1 C2 C3 5.9(3) . . . . ?
C1 O1 C2 C5 -174.10(16) . . . . ?
C4 C7 C6 C5 0.5(2) . . . . ?
C8 C7 C6 C5 -175.42(15) . . . . ?
C13 N1 C9 N2 171.70(16) . . . . ?
C11 N1 C9 N2 -5.4(3) . . . . ?
C13 N1 C9 C8 -11.4(3) . . . . ?
C11 N1 C9 C8 171.51(15) . . . . ?
S1 N2 C9 N1 -176.76(16) . . . . ?
S1 N2 C9 C8 5.83(14) . . . . ?
C10 C8 C9 N1 66.2(2) . . . . ?
C7 C8 C9 N1 -70.4(2) . . . . ?
S1 C8 C9 N1 177.38(17) . . . . ?
C10 C8 C9 N2 -116.41(16) . . . . ?
C7 C8 C9 N2 106.97(16) . . . . ?
S1 C8 C9 N2 -5.21(12) . . . . ?
C10 C8 C9 S1 -111.20(14) . . . . ?
C7 C8 C9 S1 112.18(14) . . . . ?
C7 C6 C5 C2 1.1(3) . . . . ?
O1 C2 C5 C6 177.53(15) . . . . ?
C3 C2 C5 C6 -2.4(3) . . . . ?
O1 C2 C3 C4 -177.71(16) . . . . ?
C5 C2 C3 C4 2.2(3) . . . . ?
C6 C7 C4 C3 -0.6(2) . . . . ?
C8 C7 C4 C3 175.24(16) . . . . ?
C2 C3 C4 C7 -0.7(3) . . . . ?
C9 N1 C11 C12 -84.6(2) . . . . ?
C13 N1 C11 C12 98.25(19) . . . . ?
C9 N1 C13 C14 -96.6(2) . . . . ?
C11 N1 C13 C14 80.5(2) . . . . ?

_refine_diff_density_max         0.240
_refine_diff_density_min         -0.363
_refine_diff_density_rms         0.042



_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: water'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_B_297
_database_code_depnum_ccdc_archive 'CCDC 1821396'
_audit_update_record             
;
2018-02-02 deposited with the CCDC.
2018-11-08 downloaded from the CCDC.
;
_audit_creation_date             2016-04-18
_audit_creation_method           SHELXL-2016/6
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.5
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
#------------------ CHEMICAL INFORMATION ------------------------------------# 
_chemical_name_systematic        
3-Diethylamino-4-(4-methoxyphenyl)-1,1-dioxo-4H-1λ⁶,2-thiazete-4-carbonitrile
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H17 N3 O3 S'
_chemical_formula_sum            'C14 H17 N3 O3 S'
_chemical_formula_weight         307.36

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.3830(2)
_cell_length_b                   17.5599(3)
_cell_length_c                   10.4546(2)
_cell_angle_alpha                90
_cell_angle_beta                 95.0400(9)
_cell_angle_gamma                90
_cell_volume                     1533.02(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    297(2)
_cell_measurement_reflns_used    4504
_cell_measurement_theta_min      2.2735
_cell_measurement_theta_max      21.8255

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.332
_exptl_crystal_F_000             648
_exptl_transmission_factor_min   0.8748
_exptl_transmission_factor_max   0.9459
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.175
_exptl_crystal_size_min          0.15
_exptl_absorpt_coefficient_mu    0.224
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_correction_T_min  0.8748
_exptl_absorpt_correction_T_max  0.9459
_exptl_absorpt_process_details   'SADABS-2007/4, Bruker'
_diffrn_ambient_temperature      297.15(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'sealed X-ray tube'
_diffrn_measurement_device_type  'Bruker AXS Smart APEX'
_diffrn_measurement_method       ω-scan
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            22950
_diffrn_reflns_av_unetI/netI     0.0238
_diffrn_reflns_av_R_equivalents  0.0331
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.274
_diffrn_reflns_theta_max         27.534
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3534
_reflns_number_gt                2390
_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       'Saint+(Bruker, 2007/4)'
_computing_cell_refinement       'Saint+(Bruker, 2007/4)'
_computing_data_reduction        'Saint+(Bruker, 2007/4)'
_computing_structure_solution    'SHELXS-2016 (Sheldrick, 2016)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_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)+(0.0650P)²+0.3952P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   direct
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3534
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0702
_refine_ls_R_factor_gt           0.0430
_refine_ls_wR_factor_ref         0.1322
_refine_ls_wR_factor_gt          0.1136
_refine_ls_goodness_of_fit_ref   0.988
_refine_ls_restrained_S_all      0.988
_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 0.96788(6) 0.80142(3) 0.39826(5) 0.06035(19) Uani 1 1 d . . . . .
O2 O 1.07722(18) 0.80654(11) 0.51046(16) 0.0804(5) Uani 1 1 d . . . . .
O3 O 1.03399(19) 0.79118(10) 0.27865(16) 0.0758(5) Uani 1 1 d . . . . .
N1 N 0.56076(18) 0.79803(9) 0.44230(15) 0.0508(4) Uani 1 1 d . . . . .
O1 O 0.68257(19) 0.99317(9) -0.10903(13) 0.0667(4) Uani 1 1 d . . . . .
C8 C 0.8046(2) 0.87468(11) 0.39199(17) 0.0455(4) Uani 1 1 d . . . . .
N2 N 0.8155(2) 0.74513(10) 0.41881(18) 0.0652(5) Uani 1 1 d . . . . .
C7 C 0.7638(2) 0.90962(10) 0.26105(16) 0.0438(4) Uani 1 1 d . . . . .
C2 C 0.7104(2) 0.96988(11) 0.01514(17) 0.0500(4) Uani 1 1 d . . . . .
C6 C 0.6845(2) 0.86740(11) 0.16246(18) 0.0511(5) Uani 1 1 d . . . . .
H6 H 0.6500(9) 0.8188(12) 0.1785(4) 0.061 Uiso 1 1 calc R U . . .
C9 C 0.7120(2) 0.80275(11) 0.42235(17) 0.0488(4) Uani 1 1 d . . . . .
C10 C 0.8241(2) 0.93012(12) 0.49529(19) 0.0544(5) Uani 1 1 d . . . . .
C12 C 0.4276(3) 0.69107(15) 0.3238(2) 0.0793(7) Uani 1 1 d . . . . .
H12A H 0.3772(9) 0.6398(8) 0.3349(3) 0.119 Uiso 1 1 calc R U . . .
H12B H 0.3462(13) 0.7267(6) 0.2800(8) 0.119 Uiso 1 1 calc R U . . .
H12C H 0.5208(15) 0.68560(18) 0.2700(9) 0.119 Uiso 1 1 calc R U . . .
C5 C 0.6572(2) 0.89748(12) 0.04158(19) 0.0542(5) Uani 1 1 d . . . . .
H5 H 0.5996(13) 0.8675(7) -0.0266(15) 0.065 Uiso 1 1 calc R U . . .
C3 C 0.7863(3) 1.01271(12) 0.11235(19) 0.0563(5) Uani 1 1 d . . . . .
H3 H 0.8196(9) 1.0616(13) 0.0961(5) 0.068 Uiso 1 1 calc R U . . .
C4 C 0.8129(2) 0.98248(12) 0.23458(19) 0.0538(5) Uani 1 1 d . . . . .
H4 H 0.8641(13) 1.0114(7) 0.2992(16) 0.065 Uiso 1 1 calc R U . . .
C11 C 0.4852(3) 0.72247(12) 0.4525(2) 0.0636(6) Uani 1 1 d . . . . .
H11A H 0.3983(15) 0.72662(14) 0.5030(9) 0.076 Uiso 1 1 calc R U . . .
H11B H 0.5597(13) 0.6886(6) 0.4938(8) 0.076 Uiso 1 1 calc R U . . .
C13 C 0.4623(2) 0.86580(12) 0.4609(2) 0.0587(5) Uani 1 1 d . . . . .
H13A H 0.3545(17) 0.85786(16) 0.4183(7) 0.070 Uiso 1 1 calc R U . . .
H13B H 0.5096(7) 0.9100(7) 0.4207(7) 0.070 Uiso 1 1 calc R U . . .
N3 N 0.8386(3) 0.97391(13) 0.57593(18) 0.0785(6) Uani 1 1 d . . . . .
C1 C 0.7496(3) 1.06419(14) -0.1426(2) 0.0743(7) Uani 1 1 d . . . . .
H1A H 0.7215(5) 1.0743(2) -0.2330(13) 0.111 Uiso 1 1 calc R U . . .
H1B H 0.7077(7) 1.1045(6) -0.0915(8) 0.111 Uiso 1 1 calc R U . . .
H1C H 0.8653(17) 1.06214(14) -0.1261(3) 0.111 Uiso 1 1 calc R U . . .
C14 C 0.4499(3) 0.88238(16) 0.6016(2) 0.0816(8) Uani 1 1 d . . . . .
H14A H 0.3853(10) 0.9266(7) 0.6100(3) 0.122 Uiso 1 1 calc R U . . .
H14B H 0.4021(8) 0.8399(7) 0.6408(7) 0.122 Uiso 1 1 calc R U . . .
H14C H 0.5545(17) 0.8911(2) 0.6431(7) 0.122 Uiso 1 1 calc R U . . .


_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 O3 1.4230(16) . ?
S1 O2 1.4266(17) . ?
S1 N2 1.6445(19) . ?
S1 C8 1.8754(19) . ?
S1 C9 2.182(2) . ?
N1 C9 1.305(2) . ?
N1 C13 1.471(2) . ?
N1 C11 1.478(2) . ?
O1 C2 1.361(2) . ?
O1 C1 1.424(3) . ?
C8 C10 1.453(3) . ?
C8 C7 1.512(2) . ?
C8 C9 1.530(3) . ?
N2 C9 1.335(2) . ?
C7 C4 1.379(3) . ?
C7 C6 1.391(3) . ?
C2 C3 1.375(3) . ?
C2 C5 1.383(3) . ?
C6 C5 1.370(3) . ?
C6 H6 0.92(2) . ?
C10 N3 1.140(3) . ?
C12 C11 1.494(3) . ?
C12 H12A 1.006(16) . ?
C12 H12B 1.006(16) . ?
C12 H12C 1.006(16) . ?
C5 H5 0.98(2) . ?
C3 C4 1.384(3) . ?
C3 H3 0.92(2) . ?
C4 H4 0.92(2) . ?
C11 H11A 0.940(16) . ?
C11 H11B 0.940(16) . ?
C13 C14 1.512(3) . ?
C13 H13A 0.982(15) . ?
C13 H13B 0.982(15) . ?
C1 H1A 0.971(14) . ?
C1 H1B 0.971(14) . ?
C1 H1C 0.971(14) . ?
C14 H14A 0.956(15) . ?
C14 H14B 0.956(15) . ?
C14 H14C 0.956(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
O3 S1 O2 117.31(10) . . ?
O3 S1 N2 113.95(11) . . ?
O2 S1 N2 112.39(10) . . ?
O3 S1 C8 113.29(9) . . ?
O2 S1 C8 113.57(10) . . ?
N2 S1 C8 81.01(9) . . ?
O3 S1 C9 124.44(9) . . ?
O2 S1 C9 118.14(9) . . ?
N2 S1 C9 37.65(8) . . ?
C8 S1 C9 43.50(7) . . ?
C9 N1 C13 122.27(17) . . ?
C9 N1 C11 119.79(17) . . ?
C13 N1 C11 117.89(17) . . ?
C2 O1 C1 117.36(17) . . ?
C10 C8 C7 113.77(16) . . ?
C10 C8 C9 115.16(15) . . ?
C7 C8 C9 116.38(15) . . ?
C10 C8 S1 113.54(13) . . ?
C7 C8 S1 114.61(12) . . ?
C9 C8 S1 78.97(11) . . ?
C9 N2 S1 93.57(14) . . ?
C4 C7 C6 118.51(17) . . ?
C4 C7 C8 120.69(17) . . ?
C6 C7 C8 120.68(17) . . ?
O1 C2 C3 124.74(18) . . ?
O1 C2 C5 115.82(17) . . ?
C3 C2 C5 119.45(18) . . ?
C5 C6 C7 120.55(19) . . ?
C5 C6 H6 119.7 . . ?
C7 C6 H6 119.7 . . ?
N1 C9 N2 126.77(18) . . ?
N1 C9 C8 127.09(17) . . ?
N2 C9 C8 106.09(16) . . ?
N1 C9 S1 175.03(15) . . ?
N2 C9 S1 48.78(10) . . ?
C8 C9 S1 57.53(9) . . ?
N3 C10 C8 179.5(2) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C6 C5 C2 120.53(19) . . ?
C6 C5 H5 119.7 . . ?
C2 C5 H5 119.7 . . ?
C2 C3 C4 119.94(19) . . ?
C2 C3 H3 120.0 . . ?
C4 C3 H3 120.0 . . ?
C7 C4 C3 120.98(19) . . ?
C7 C4 H4 119.5 . . ?
C3 C4 H4 119.5 . . ?
N1 C11 C12 111.90(18) . . ?
N1 C11 H11A 109.2 . . ?
C12 C11 H11A 109.2 . . ?
N1 C11 H11B 109.2 . . ?
C12 C11 H11B 109.2 . . ?
H11A C11 H11B 107.9 . . ?
N1 C13 C14 111.85(18) . . ?
N1 C13 H13A 109.2 . . ?
C14 C13 H13A 109.2 . . ?
N1 C13 H13B 109.2 . . ?
C14 C13 H13B 109.2 . . ?
H13A C13 H13B 107.9 . . ?
O1 C1 H1A 109.5 . . ?
O1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
O1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?

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
O3 S1 C8 C10 -131.04(15) . . . . ?
O2 S1 C8 C10 6.07(17) . . . . ?
N2 S1 C8 C10 116.67(15) . . . . ?
C9 S1 C8 C10 112.80(17) . . . . ?
O3 S1 C8 C7 2.04(17) . . . . ?
O2 S1 C8 C7 139.16(14) . . . . ?
N2 S1 C8 C7 -110.25(15) . . . . ?
C9 S1 C8 C7 -114.12(17) . . . . ?
O3 S1 C8 C9 116.16(12) . . . . ?
O2 S1 C8 C9 -106.73(12) . . . . ?
N2 S1 C8 C9 3.87(11) . . . . ?
O3 S1 N2 C9 -115.93(13) . . . . ?
O2 S1 N2 C9 107.52(14) . . . . ?
C8 S1 N2 C9 -4.36(12) . . . . ?
C10 C8 C7 C4 28.1(2) . . . . ?
C9 C8 C7 C4 165.54(17) . . . . ?
S1 C8 C7 C4 -104.90(18) . . . . ?
C10 C8 C7 C6 -155.84(17) . . . . ?
C9 C8 C7 C6 -18.4(2) . . . . ?
S1 C8 C7 C6 71.19(19) . . . . ?
C1 O1 C2 C3 5.9(3) . . . . ?
C1 O1 C2 C5 -173.87(19) . . . . ?
C4 C7 C6 C5 0.6(3) . . . . ?
C8 C7 C6 C5 -175.60(17) . . . . ?
C13 N1 C9 N2 171.86(19) . . . . ?
C11 N1 C9 N2 -5.4(3) . . . . ?
C13 N1 C9 C8 -11.3(3) . . . . ?
C11 N1 C9 C8 171.44(18) . . . . ?
S1 N2 C9 N1 -177.13(18) . . . . ?
S1 N2 C9 C8 5.49(16) . . . . ?
C10 C8 C9 N1 66.8(3) . . . . ?
C7 C8 C9 N1 -70.1(2) . . . . ?
S1 C8 C9 N1 177.74(19) . . . . ?
C10 C8 C9 N2 -115.87(18) . . . . ?
C7 C8 C9 N2 107.24(18) . . . . ?
S1 C8 C9 N2 -4.90(14) . . . . ?
C10 C8 C9 S1 -110.97(16) . . . . ?
C7 C8 C9 S1 112.14(15) . . . . ?
C7 C6 C5 C2 1.0(3) . . . . ?
O1 C2 C5 C6 177.53(18) . . . . ?
C3 C2 C5 C6 -2.2(3) . . . . ?
O1 C2 C3 C4 -177.96(19) . . . . ?
C5 C2 C3 C4 1.8(3) . . . . ?
C6 C7 C4 C3 -1.0(3) . . . . ?
C8 C7 C4 C3 175.15(18) . . . . ?
C2 C3 C4 C7 -0.2(3) . . . . ?
C9 N1 C11 C12 -85.4(3) . . . . ?
C13 N1 C11 C12 97.2(2) . . . . ?
C9 N1 C13 C14 -97.0(2) . . . . ?
C11 N1 C13 C14 80.3(2) . . . . ?

_refine_diff_density_max         0.186
_refine_diff_density_min         -0.319
_refine_diff_density_rms         0.037



_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: water'
