# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2019

####################################################################### 
# 
# 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_exp_458
_database_code_depnum_ccdc_archive 'CCDC 1878314'
_audit_update_record             
;
2018-11-11 deposited with the CCDC.
2019-01-08 downloaded from the CCDC.
;
_audit_creation_date             2018-07-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H17 N3 O2'
_chemical_formula_sum            'C20 H17 N3 O2'
_chemical_formula_weight         331.36
_chemical_absolute_configuration ?
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           43
_space_group_name_H-M_alt        'F d d 2'
_space_group_name_Hall           'F 2 -2d'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'-x+1/4, y+1/4, z+1/4'
'x+1/4, -y+1/4, z+1/4'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'-x+1/4, y+3/4, z+3/4'
'x+1/4, -y+3/4, z+3/4'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'-x+3/4, y+1/4, z+3/4'
'x+3/4, -y+1/4, z+3/4'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'-x+3/4, y+3/4, z+1/4'
'x+3/4, -y+3/4, z+1/4'

_cell_length_a                   26.1810(10)
_cell_length_b                   24.1800(8)
_cell_length_c                   10.7074(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     6778.4(4)
_cell_formula_units_Z            16
_cell_measurement_reflns_used    3299
_cell_measurement_temperature    290
_cell_measurement_theta_max      26.6500
_cell_measurement_theta_min      3.9240
_shelx_estimated_absorpt_T_max   0.983
_shelx_estimated_absorpt_T_min   0.966
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.78802
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             2784
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0258
_diffrn_reflns_av_unetI/netI     0.0307
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.896
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            8634
_diffrn_reflns_point_group_measured_fraction_full 0.777
_diffrn_reflns_point_group_measured_fraction_max 0.655
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.494
_diffrn_reflns_theta_min         3.112
_diffrn_ambient_temperature      290.0
_diffrn_detector_area_resol_mean 10.3974
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.896
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   -3.00   38.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -        9.8158  -99.0000  -60.0000 41

#__ type_ start__ end____ width___ exp.time_
  2 omega  -45.00   41.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -        9.8158  -77.0000   90.0000 86

#__ type_ start__ end____ width___ exp.time_
  3 omega   24.00   79.00   1.0000   50.0000
omega____ theta____ kappa____ phi______ frames
    -        9.8158   57.0000 -180.0000 55
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.393
_reflns_Friedel_fraction_full    0.530
_reflns_Friedel_fraction_max     0.389
_reflns_number_gt                2251
_reflns_number_total             3102
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.124
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details 
;
 Flack x determined using 592 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.2(9)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.102
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     232
_refine_ls_number_reflns         3102
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0787
_refine_ls_R_factor_gt           0.0497
_refine_ls_restrained_S_all      1.101
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0394P)²+6.6334P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1072
_refine_ls_wR_factor_ref         0.1210
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C9(H9), C6(H6), C11(H11), C19(H19), C14(H14), C10(H10), C17(H17), C16(H16),
 C12(H12), C18(H18)
2.b Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C), C1(H1A,H1B,H1C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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
C7 C 0.05905(11) 0.03346(13) 0.3575(3) 0.0452(8) Uani 1 1 d . . . . .
N2 N 0.02696(10) 0.15469(11) 0.5433(3) 0.0478(7) Uani 1 1 d . . . . .
C13 C 0.08976(12) -0.06193(14) 0.3760(4) 0.0571(10) Uani 1 1 d . . . . .
O4 O 0.02833(11) 0.20171(11) 0.3564(3) 0.0680(8) Uani 1 1 d . . . . .
C4 C 0.02044(13) 0.19977(14) 0.4683(3) 0.0511(9) Uani 1 1 d . . . . .
C15 C 0.08092(13) -0.02033(16) 0.1693(4) 0.0610(10) Uani 1 1 d . . . . .
C9 C 0.06595(14) -0.01281(15) 0.5664(4) 0.0594(10) Uani 1 1 d . . . . .
H9 H 0.054093 0.018596 0.607293 0.071 Uiso 1 1 calc R . . . .
C20 C 0.06360(12) 0.02998(15) 0.2266(3) 0.0510(9) Uani 1 1 d . . . . .
C5 C 0.01652(14) 0.16716(15) 0.6705(4) 0.0566(9) Uani 1 1 d . . . . .
C6 C 0.03805(12) 0.08471(13) 0.4078(3) 0.0493(8) Uani 1 1 d . . . . .
H6 H 0.014975 0.104302 0.358777 0.059 Uiso 1 1 calc R . . . .
C8 C 0.07207(11) -0.01230(14) 0.4346(4) 0.0493(9) Uani 1 1 d . . . . .
C11 C 0.09540(16) -0.10731(17) 0.5753(5) 0.0729(12) Uani 1 1 d . . . . .
H11 H 0.103188 -0.138223 0.623307 0.088 Uiso 1 1 calc R . . . .
O5 O 0.02013(11) 0.13494(11) 0.7550(3) 0.0727(8) Uani 1 1 d . . . . .
C19 C 0.05170(14) 0.07467(17) 0.1444(4) 0.0643(10) Uani 1 1 d . . . . .
H19 H 0.041523 0.108417 0.177793 0.077 Uiso 1 1 calc R . . . .
N3 N 0.04928(10) 0.10411(11) 0.5138(3) 0.0533(7) Uani 1 1 d . . . . .
N1 N 0.00194(15) 0.22039(14) 0.6717(3) 0.0706(10) Uani 1 1 d . . . . .
C14 C 0.09348(13) -0.06454(16) 0.2463(4) 0.0660(11) Uani 1 1 d . . . . .
H14 H 0.104827 -0.097202 0.209832 0.079 Uiso 1 1 calc R . . . .
C3 C 0.00281(14) 0.24676(14) 0.5498(4) 0.0551(9) Uani 1 1 d . . . . .
C2 C -0.05030(14) 0.26635(15) 0.5107(4) 0.0669(10) Uani 1 1 d . . . . .
H2A H -0.048423 0.283231 0.429636 0.100 Uiso 1 1 calc GR . . . .
H2B H -0.062731 0.292827 0.570144 0.100 Uiso 1 1 calc GR . . . .
H2C H -0.073118 0.235301 0.507574 0.100 Uiso 1 1 calc GR . . . .
C1 C 0.04137(15) 0.29447(15) 0.5449(5) 0.0787(13) Uani 1 1 d . . . . .
H1A H 0.074282 0.281409 0.571240 0.118 Uiso 1 1 calc GR . . . .
H1B H 0.030328 0.323618 0.599520 0.118 Uiso 1 1 calc GR . . . .
H1C H 0.043626 0.308253 0.461047 0.118 Uiso 1 1 calc GR . . . .
C10 C 0.07736(15) -0.05894(16) 0.6327(4) 0.0684(11) Uani 1 1 d . . . . .
H10 H 0.073104 -0.058511 0.718926 0.082 Uiso 1 1 calc R . . . .
C17 C 0.0716(2) 0.0200(2) -0.0360(5) 0.0909(15) Uani 1 1 d . . . . .
H17 H 0.073699 0.016996 -0.122486 0.109 Uiso 1 1 calc R . . . .
C16 C 0.08494(18) -0.0237(2) 0.0379(5) 0.0825(14) Uani 1 1 d . . . . .
H16 H 0.096828 -0.056131 0.001320 0.099 Uiso 1 1 calc R . . . .
C12 C 0.10137(14) -0.10882(16) 0.4508(5) 0.0696(12) Uani 1 1 d . . . . .
H12 H 0.113258 -0.140973 0.412999 0.084 Uiso 1 1 calc R . . . .
C18 C 0.05493(17) 0.06896(19) 0.0187(4) 0.0797(12) Uani 1 1 d . . . . .
H18 H 0.045766 0.098500 -0.032227 0.096 Uiso 1 1 calc R . . . .
H1 H -0.0107(17) 0.2359(18) 0.739(4) 0.084(15) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C7 C20 1.409(5) . ?
C7 C6 1.459(4) . ?
C7 C8 1.422(5) . ?
N2 C4 1.365(4) . ?
N2 C5 1.422(4) . ?
N2 N3 1.392(4) . ?
C13 C8 1.431(5) . ?
C13 C14 1.393(6) . ?
C13 C12 1.421(5) . ?
O4 C4 1.217(4) . ?
C4 C3 1.505(5) . ?
C15 C20 1.436(5) . ?
C15 C14 1.390(6) . ?
C15 C16 1.413(6) . ?
C9 H9 0.9300 . ?
C9 C8 1.420(5) . ?
C9 C10 1.356(5) . ?
C20 C19 1.428(5) . ?
C5 O5 1.198(4) . ?
C5 N1 1.343(5) . ?
C6 H6 0.9300 . ?
C6 N3 1.263(4) . ?
C11 H11 0.9300 . ?
C11 C10 1.403(6) . ?
C11 C12 1.343(6) . ?
C19 H19 0.9300 . ?
C19 C18 1.355(6) . ?
N1 C3 1.452(5) . ?
N1 H1 0.88(5) . ?
C14 H14 0.9300 . ?
C3 C2 1.528(5) . ?
C3 C1 1.534(5) . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C10 H10 0.9300 . ?
C17 H17 0.9300 . ?
C17 C16 1.365(7) . ?
C17 C18 1.392(6) . ?
C16 H16 0.9300 . ?
C12 H12 0.9300 . ?
C18 H18 0.9300 . ?

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
C20 C7 C6 116.7(3) . . ?
C20 C7 C8 120.7(3) . . ?
C8 C7 C6 122.5(3) . . ?
C4 N2 C5 111.7(3) . . ?
C4 N2 N3 128.4(3) . . ?
N3 N2 C5 119.0(3) . . ?
C14 C13 C8 119.8(4) . . ?
C14 C13 C12 120.7(4) . . ?
C12 C13 C8 119.4(4) . . ?
N2 C4 C3 107.5(3) . . ?
O4 C4 N2 126.1(3) . . ?
O4 C4 C3 126.4(3) . . ?
C14 C15 C20 118.2(4) . . ?
C14 C15 C16 121.9(4) . . ?
C16 C15 C20 119.9(4) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 H9 119.9 . . ?
C10 C9 C8 120.2(4) . . ?
C7 C20 C15 120.1(3) . . ?
C7 C20 C19 123.3(3) . . ?
C19 C20 C15 116.5(3) . . ?
O5 C5 N2 124.8(3) . . ?
O5 C5 N1 129.7(4) . . ?
N1 C5 N2 105.5(3) . . ?
C7 C6 H6 118.0 . . ?
N3 C6 C7 124.0(3) . . ?
N3 C6 H6 118.0 . . ?
C7 C8 C13 118.4(3) . . ?
C9 C8 C7 123.8(3) . . ?
C9 C8 C13 117.7(3) . . ?
C10 C11 H11 120.1 . . ?
C12 C11 H11 120.1 . . ?
C12 C11 C10 119.8(4) . . ?
C20 C19 H19 119.3 . . ?
C18 C19 C20 121.4(4) . . ?
C18 C19 H19 119.3 . . ?
C6 N3 N2 115.6(3) . . ?
C5 N1 C3 114.1(3) . . ?
C5 N1 H1 122(3) . . ?
C3 N1 H1 124(3) . . ?
C13 C14 H14 118.7 . . ?
C15 C14 C13 122.7(4) . . ?
C15 C14 H14 118.7 . . ?
C4 C3 C2 110.7(3) . . ?
C4 C3 C1 110.3(3) . . ?
N1 C3 C4 101.2(3) . . ?
N1 C3 C2 111.6(3) . . ?
N1 C3 C1 111.8(3) . . ?
C2 C3 C1 110.9(3) . . ?
C3 C2 H2A 109.5 . . ?
C3 C2 H2B 109.5 . . ?
C3 C2 H2C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C3 C1 H1A 109.5 . . ?
C3 C1 H1B 109.5 . . ?
C3 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C9 C10 C11 122.0(4) . . ?
C9 C10 H10 119.0 . . ?
C11 C10 H10 119.0 . . ?
C16 C17 H17 120.2 . . ?
C16 C17 C18 119.6(4) . . ?
C18 C17 H17 120.2 . . ?
C15 C16 H16 119.5 . . ?
C17 C16 C15 120.9(4) . . ?
C17 C16 H16 119.5 . . ?
C13 C12 H12 119.6 . . ?
C11 C12 C13 120.9(4) . . ?
C11 C12 H12 119.6 . . ?
C19 C18 C17 121.6(5) . . ?
C19 C18 H18 119.2 . . ?
C17 C18 H18 119.2 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C6 H6 O4 0.93 2.38 2.893(4) 114.5 .
N1 H1 O4 0.88(5) 2.02(5) 2.844(4) 157(4) 6

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 C20 C19 C18 -177.7(4) . . . . ?
C7 C6 N3 N2 177.4(3) . . . . ?
N2 C4 C3 N1 0.6(4) . . . . ?
N2 C4 C3 C2 -117.9(3) . . . . ?
N2 C4 C3 C1 119.0(3) . . . . ?
N2 C5 N1 C3 -1.4(4) . . . . ?
O4 C4 C3 N1 -178.2(4) . . . . ?
O4 C4 C3 C2 63.3(5) . . . . ?
O4 C4 C3 C1 -59.8(5) . . . . ?
C4 N2 C5 O5 -178.9(4) . . . . ?
C4 N2 C5 N1 1.8(4) . . . . ?
C4 N2 N3 C6 -41.4(5) . . . . ?
C15 C20 C19 C18 2.3(6) . . . . ?
C20 C7 C6 N3 -150.6(3) . . . . ?
C20 C7 C8 C13 -0.1(5) . . . . ?
C20 C7 C8 C9 -176.6(3) . . . . ?
C20 C15 C14 C13 0.2(5) . . . . ?
C20 C15 C16 C17 -1.3(7) . . . . ?
C20 C19 C18 C17 -2.2(7) . . . . ?
C5 N2 C4 O4 177.3(4) . . . . ?
C5 N2 C4 C3 -1.5(4) . . . . ?
C5 N2 N3 C6 150.4(3) . . . . ?
C5 N1 C3 C4 0.5(4) . . . . ?
C5 N1 C3 C2 118.4(4) . . . . ?
C5 N1 C3 C1 -116.8(4) . . . . ?
C6 C7 C20 C15 -176.1(3) . . . . ?
C6 C7 C20 C19 3.9(5) . . . . ?
C6 C7 C8 C13 176.6(3) . . . . ?
C6 C7 C8 C9 0.1(5) . . . . ?
C8 C7 C20 C15 0.8(5) . . . . ?
C8 C7 C20 C19 -179.2(3) . . . . ?
C8 C7 C6 N3 32.6(5) . . . . ?
C8 C13 C14 C15 0.4(5) . . . . ?
C8 C13 C12 C11 0.8(6) . . . . ?
C8 C9 C10 C11 0.0(6) . . . . ?
O5 C5 N1 C3 179.4(4) . . . . ?
N3 N2 C4 O4 8.4(6) . . . . ?
N3 N2 C4 C3 -170.4(3) . . . . ?
N3 N2 C5 O5 -8.9(5) . . . . ?
N3 N2 C5 N1 171.9(3) . . . . ?
C14 C13 C8 C7 -0.5(5) . . . . ?
C14 C13 C8 C9 176.2(3) . . . . ?
C14 C13 C12 C11 -176.7(4) . . . . ?
C14 C15 C20 C7 -0.8(5) . . . . ?
C14 C15 C20 C19 179.2(3) . . . . ?
C14 C15 C16 C17 179.0(4) . . . . ?
C10 C9 C8 C7 177.3(3) . . . . ?
C10 C9 C8 C13 0.8(5) . . . . ?
C10 C11 C12 C13 0.1(7) . . . . ?
C16 C15 C20 C7 179.4(3) . . . . ?
C16 C15 C20 C19 -0.6(5) . . . . ?
C16 C15 C14 C13 180.0(4) . . . . ?
C16 C17 C18 C19 0.3(7) . . . . ?
C12 C13 C8 C7 -177.9(3) . . . . ?
C12 C13 C8 C9 -1.2(5) . . . . ?
C12 C13 C14 C15 177.8(3) . . . . ?
C12 C11 C10 C9 -0.6(6) . . . . ?
C18 C17 C16 C15 1.5(7) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_exp_467
_database_code_depnum_ccdc_archive 'CCDC 1878316'
_audit_update_record             
;
2018-11-11 deposited with the CCDC.
2019-01-08 downloaded from the CCDC.
;
_audit_creation_date             2018-07-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H12 N4 O4'
_chemical_formula_sum            'C12 H12 N4 O4'
_chemical_formula_weight         276.26
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C20 H20 N3 O3'
_chemical_oxdiff_usercomment     SB3
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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.9932(6)
_cell_length_b                   10.2222(11)
_cell_length_c                   10.8532(11)
_cell_angle_alpha                95.690(9)
_cell_angle_beta                 101.192(9)
_cell_angle_gamma                103.562(9)
_cell_volume                     626.73(12)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1049
_cell_measurement_temperature    150
_cell_measurement_theta_max      26.8460
_cell_measurement_theta_min      3.0320
_shelx_estimated_absorpt_T_max   0.976
_shelx_estimated_absorpt_T_min   0.967
_exptl_absorpt_coefficient_mu    0.113
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67474
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.464
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             288
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.22
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0469
_diffrn_reflns_av_unetI/netI     0.0728
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4301
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.027
_diffrn_reflns_theta_max         25.027
_diffrn_reflns_theta_min         3.044
_diffrn_ambient_temperature      150
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.3974
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -18.00   31.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.3019 -102.0000 -164.0000 49

#__ type_ start__ end____ width___ exp.time_
  2 omega  -48.00   -9.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.3019  102.0000  -61.0000 39

#__ type_ start__ end____ width___ exp.time_
  3 omega  -78.00   13.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.3019  -38.0000   30.0000 91

#__ type_ start__ end____ width___ exp.time_
  4 omega  -45.00   55.00   1.0000   15.0000
omega____ theta____ kappa____ phi______ frames
    -       -8.3019    0.0000 -120.0000 100
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.1015301000
_diffrn_orient_matrix_UB_12      0.0054732000
_diffrn_orient_matrix_UB_13      -0.0255749000
_diffrn_orient_matrix_UB_21      -0.0719152000
_diffrn_orient_matrix_UB_22      -0.0348727000
_diffrn_orient_matrix_UB_23      -0.0594127000
_diffrn_orient_matrix_UB_31      -0.0114027000
_diffrn_orient_matrix_UB_32      0.0629983000
_diffrn_orient_matrix_UB_33      -0.0189465000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1489
_reflns_number_total             2209
_reflns_odcompleteness_completeness 99.82
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     24.97
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.199
_refine_diff_density_min         -0.287
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     187
_refine_ls_number_reflns         2209
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0915
_refine_ls_R_factor_gt           0.0564
_refine_ls_restrained_S_all      1.041
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0619P)²+0.0692P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1246
_refine_ls_wR_factor_ref         0.1491
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C8(H8), C9(H9), C12(H12), C11(H11)
2.b Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C), C1(H1A,H1B,H1C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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
O5 O 0.2992(3) 0.52304(17) 0.10650(17) 0.0310(5) Uani 1 1 d . . . . .
O4 O 0.7028(3) 0.87279(18) -0.06642(18) 0.0335(5) Uani 1 1 d . . . . .
N3 N 0.7410(4) 0.7023(2) 0.1441(2) 0.0270(6) Uani 1 1 d . . . . .
N2 N 0.5511(4) 0.7083(2) 0.0503(2) 0.0263(6) Uani 1 1 d . . . . .
N1 N 0.1903(4) 0.6249(2) -0.0681(2) 0.0287(6) Uani 1 1 d . . . . .
C6 C 0.9252(5) 0.8026(3) 0.1692(3) 0.0284(7) Uani 1 1 d . . . . .
H6 H 0.927897 0.880788 0.128371 0.034 Uiso 1 1 calc R . . . .
N4 N 1.7493(4) 0.7667(2) 0.5103(2) 0.0374(7) Uani 1 1 d . . . . .
C7 C 1.1326(5) 0.7938(2) 0.2630(2) 0.0257(7) Uani 1 1 d . . . . .
O1 O 1.7557(4) 0.6565(2) 0.5441(2) 0.0548(7) Uani 1 1 d . . . . .
C5 C 0.3356(5) 0.6067(2) 0.0345(3) 0.0255(6) Uani 1 1 d . . . . .
O2 O 1.9161(4) 0.8672(2) 0.5434(2) 0.0601(8) Uani 1 1 d . . . . .
C8 C 1.1341(5) 0.6795(3) 0.3233(3) 0.0310(7) Uani 1 1 d . . . . .
H8 H 0.994904 0.607278 0.308134 0.037 Uiso 1 1 calc R . . . .
C10 C 1.5328(5) 0.7772(3) 0.4264(3) 0.0289(7) Uani 1 1 d . . . . .
C9 C 1.3349(5) 0.6703(3) 0.4045(3) 0.0303(7) Uani 1 1 d . . . . .
H9 H 1.336701 0.591866 0.444434 0.036 Uiso 1 1 calc R . . . .
C12 C 1.3351(5) 0.9008(3) 0.2882(3) 0.0305(7) Uani 1 1 d . . . . .
H12 H 1.334387 0.979147 0.248054 0.037 Uiso 1 1 calc R . . . .
C4 C 0.5442(5) 0.7827(2) -0.0494(2) 0.0258(7) Uani 1 1 d . . . . .
C11 C 1.5376(5) 0.8943(3) 0.3711(3) 0.0322(7) Uani 1 1 d . . . . .
H11 H 1.675642 0.967674 0.389709 0.039 Uiso 1 1 calc R . . . .
C2 C 0.3254(5) 0.6682(3) -0.2661(3) 0.0358(7) Uani 1 1 d . . . . .
H2A H 0.401149 0.593523 -0.255719 0.054 Uiso 1 1 calc GR . . . .
H2B H 0.421585 0.738430 -0.302903 0.054 Uiso 1 1 calc GR . . . .
H2C H 0.168858 0.633223 -0.322629 0.054 Uiso 1 1 calc GR . . . .
C1 C 0.1748(5) 0.8421(3) -0.1474(3) 0.0368(8) Uani 1 1 d . . . . .
H1A H 0.014119 0.804498 -0.198600 0.055 Uiso 1 1 calc GR . . . .
H1B H 0.259949 0.913304 -0.187968 0.055 Uiso 1 1 calc GR . . . .
H1C H 0.168923 0.881172 -0.062247 0.055 Uiso 1 1 calc GR . . . .
C3 C 0.3015(5) 0.7292(3) -0.1370(3) 0.0277(7) Uani 1 1 d . . . . .
H1 H 0.045(7) 0.579(3) -0.090(3) 0.057(11) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O5 C5 1.224(3) . ?
O4 C4 1.216(3) . ?
N3 N2 1.389(3) . ?
N3 C6 1.281(3) . ?
N2 C5 1.424(3) . ?
N2 C4 1.383(3) . ?
N1 C5 1.332(3) . ?
N1 C3 1.470(3) . ?
N1 H1 0.86(4) . ?
C6 H6 0.9500 . ?
C6 C7 1.473(4) . ?
N4 O1 1.225(3) . ?
N4 O2 1.221(3) . ?
N4 C10 1.467(4) . ?
C7 C8 1.395(3) . ?
C7 C12 1.390(4) . ?
C8 H8 0.9500 . ?
C8 C9 1.375(4) . ?
C10 C9 1.374(4) . ?
C10 C11 1.388(3) . ?
C9 H9 0.9500 . ?
C12 H12 0.9500 . ?
C12 C11 1.383(4) . ?
C4 C3 1.519(4) . ?
C11 H11 0.9500 . ?
C2 H2A 0.9800 . ?
C2 H2B 0.9800 . ?
C2 H2C 0.9800 . ?
C2 C3 1.523(4) . ?
C1 H1A 0.9800 . ?
C1 H1B 0.9800 . ?
C1 H1C 0.9800 . ?
C1 C3 1.525(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 N3 N2 117.9(2) . . ?
N3 N2 C5 117.89(19) . . ?
C4 N2 N3 130.0(2) . . ?
C4 N2 C5 110.9(2) . . ?
C5 N1 C3 113.8(2) . . ?
C5 N1 H1 122(2) . . ?
C3 N1 H1 125(2) . . ?
N3 C6 H6 120.8 . . ?
N3 C6 C7 118.4(2) . . ?
C7 C6 H6 120.8 . . ?
O1 N4 C10 118.4(2) . . ?
O2 N4 O1 122.5(2) . . ?
O2 N4 C10 119.1(2) . . ?
C8 C7 C6 122.0(2) . . ?
C12 C7 C6 118.7(2) . . ?
C12 C7 C8 119.3(3) . . ?
O5 C5 N2 124.1(2) . . ?
O5 C5 N1 129.1(3) . . ?
N1 C5 N2 106.8(2) . . ?
C7 C8 H8 119.6 . . ?
C9 C8 C7 120.8(3) . . ?
C9 C8 H8 119.6 . . ?
C9 C10 N4 118.8(2) . . ?
C9 C10 C11 122.8(3) . . ?
C11 C10 N4 118.4(2) . . ?
C8 C9 H9 120.8 . . ?
C10 C9 C8 118.4(2) . . ?
C10 C9 H9 120.8 . . ?
C7 C12 H12 119.6 . . ?
C11 C12 C7 120.7(2) . . ?
C11 C12 H12 119.6 . . ?
O4 C4 N2 127.0(3) . . ?
O4 C4 C3 125.6(2) . . ?
N2 C4 C3 107.4(2) . . ?
C10 C11 H11 121.0 . . ?
C12 C11 C10 117.9(2) . . ?
C12 C11 H11 121.0 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C3 C2 H2A 109.5 . . ?
C3 C2 H2B 109.5 . . ?
C3 C2 H2C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C1 H1A 109.5 . . ?
C3 C1 H1B 109.5 . . ?
C3 C1 H1C 109.5 . . ?
N1 C3 C4 100.8(2) . . ?
N1 C3 C2 112.1(2) . . ?
N1 C3 C1 111.5(2) . . ?
C4 C3 C2 109.4(2) . . ?
C4 C3 C1 110.4(2) . . ?
C2 C3 C1 112.0(2) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C6 H6 O4 0.95 2.26 2.885(3) 122.6 .
C9 H9 O1 0.95 2.49 3.377(3) 155.5 2_866
C11 H11 O2 0.95 2.55 3.486(4) 169.4 2_976
C1 H1C O4 0.98 2.62 3.378(4) 134.6 2_675
N1 H1 O5 0.86(4) 2.05(4) 2.896(3) 170(3) 2_565

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
O4 C4 C3 N1 -179.7(3) . . . . ?
O4 C4 C3 C2 62.0(3) . . . . ?
O4 C4 C3 C1 -61.7(3) . . . . ?
N3 N2 C5 O5 8.0(4) . . . . ?
N3 N2 C5 N1 -173.5(2) . . . . ?
N3 N2 C4 O4 -10.0(5) . . . . ?
N3 N2 C4 C3 168.7(2) . . . . ?
N3 C6 C7 C8 0.8(4) . . . . ?
N3 C6 C7 C12 178.3(3) . . . . ?
N2 N3 C6 C7 -176.5(2) . . . . ?
N2 C4 C3 N1 1.6(3) . . . . ?
N2 C4 C3 C2 -116.7(2) . . . . ?
N2 C4 C3 C1 119.6(2) . . . . ?
C6 N3 N2 C5 -171.4(2) . . . . ?
C6 N3 N2 C4 22.4(4) . . . . ?
C6 C7 C8 C9 175.9(3) . . . . ?
C6 C7 C12 C11 -177.0(3) . . . . ?
N4 C10 C9 C8 -178.5(3) . . . . ?
N4 C10 C11 C12 177.5(3) . . . . ?
C7 C8 C9 C10 1.0(4) . . . . ?
C7 C12 C11 C10 1.0(4) . . . . ?
O1 N4 C10 C9 9.8(4) . . . . ?
O1 N4 C10 C11 -169.4(3) . . . . ?
C5 N2 C4 O4 -176.9(3) . . . . ?
C5 N2 C4 C3 1.8(3) . . . . ?
C5 N1 C3 C4 -4.8(3) . . . . ?
C5 N1 C3 C2 111.5(3) . . . . ?
C5 N1 C3 C1 -122.0(3) . . . . ?
O2 N4 C10 C9 -170.6(3) . . . . ?
O2 N4 C10 C11 10.2(4) . . . . ?
C8 C7 C12 C11 0.6(4) . . . . ?
C9 C10 C11 C12 -1.7(4) . . . . ?
C12 C7 C8 C9 -1.7(4) . . . . ?
C4 N2 C5 O5 176.7(3) . . . . ?
C4 N2 C5 N1 -4.8(3) . . . . ?
C11 C10 C9 C8 0.7(4) . . . . ?
C3 N1 C5 O5 -175.5(3) . . . . ?
C3 N1 C5 N2 6.0(3) . . . . ?

_olex2_date_sample_data_collection 2018-07-02
_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_exp_453
_database_code_depnum_ccdc_archive 'CCDC 1878315'
_audit_update_record             
;
2018-11-11 deposited with the CCDC.
2019-01-08 downloaded from the CCDC.
;
_audit_creation_date             2018-07-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H13 N3 O3'
_chemical_formula_sum            'C12 H13 N3 O3'
_chemical_formula_weight         247.25
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   21.3276(8)
_cell_length_b                   5.8210(3)
_cell_length_c                   20.1338(9)
_cell_angle_alpha                90
_cell_angle_beta                 100.475(4)
_cell_angle_gamma                90
_cell_volume                     2457.92(18)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4478
_cell_measurement_temperature    290
_cell_measurement_theta_max      27.0160
_cell_measurement_theta_min      4.0780
_shelx_estimated_absorpt_T_max   0.988
_shelx_estimated_absorpt_T_min   0.971
_exptl_absorpt_coefficient_mu    0.098
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.57165
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.336
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             1040
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0406
_diffrn_reflns_av_unetI/netI     0.0311
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.901
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            14020
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.901
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.167
_diffrn_reflns_theta_min         3.076
_diffrn_ambient_temperature      290.0
_diffrn_detector_area_resol_mean 10.3974
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.901
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     15.00  53.00   1.00   17.50    --    8.44  38.00  60.00   38
  2  ω      1.00  27.00   1.00   17.50    --    8.44 -57.00  60.00   26
  3  ω    -43.00  35.00   1.00   17.50    --    8.44 -57.00 -60.00   78
  4  ω     24.00  80.00   1.00   17.50    --    8.44  38.00 120.00   56
  5  ω    -10.00  48.00   1.00   17.50    --    8.44  57.00 -90.00   58
  6  ω     22.00  70.00   1.00   17.50    --    8.44  38.00-180.00   48
  7  ω    -60.00 -19.00   1.00   17.50    --    8.44 -38.00-150.00   41
  8  ω     48.00  77.00   1.00   17.50    --    8.44  57.00 -60.00   29
  9  ω    -20.00   5.00   1.00   17.50    --   -9.06 -99.00-180.00   25
 10  ω     -8.00  30.00   1.00   17.50    --   -9.06 -99.00   0.00   38
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1991
_reflns_number_total             2973
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.147
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2973
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0822
_refine_ls_R_factor_gt           0.0516
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0510P)²+1.9360P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1227
_refine_ls_wR_factor_ref         0.1420
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C12(H12), C11(H11), C9(H9), C10(H10)
2.b Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C), C1(H1A,H1B,H1C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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
N3 N 0.11038(7) 0.9006(3) 0.07709(7) 0.0446(4) Uani 1 1 d . . . . .
N2 N 0.10776(7) 1.0649(3) 0.02724(7) 0.0430(4) Uani 1 1 d . . . . .
O5 O 0.01767(6) 1.2366(2) 0.05604(7) 0.0563(4) Uani 1 1 d . . . . .
O4 O 0.19137(6) 0.9833(2) -0.02786(7) 0.0574(4) Uani 1 1 d . . . . .
C7 C 0.16074(8) 0.5857(3) 0.13945(9) 0.0425(4) Uani 1 1 d . . . . .
N1 N 0.05964(8) 1.3423(3) -0.03699(8) 0.0530(5) Uani 1 1 d . . . . .
C4 C 0.14353(8) 1.0889(3) -0.02272(9) 0.0435(4) Uani 1 1 d . . . . .
O8 O 0.06172(7) 0.6934(3) 0.17246(9) 0.0790(6) Uani 1 1 d . . . . .
C6 C 0.15897(9) 0.7672(3) 0.09019(9) 0.0447(4) Uani 1 1 d . . . . .
H6 H 0.193137 0.787404 0.067921 0.054 Uiso 1 1 calc R . . . .
C5 C 0.05590(9) 1.2224(3) 0.01812(9) 0.0449(4) Uani 1 1 d . . . . .
C12 C 0.21180(9) 0.4311(3) 0.14861(9) 0.0491(5) Uani 1 1 d . . . . .
H12 H 0.244032 0.450221 0.123581 0.059 Uiso 1 1 calc R . . . .
C3 C 0.11070(9) 1.2682(3) -0.07162(9) 0.0457(4) Uani 1 1 d . . . . .
C8 C 0.11279(9) 0.5531(4) 0.17770(10) 0.0532(5) Uani 1 1 d . . . . .
C11 C 0.21567(10) 0.2526(4) 0.19334(10) 0.0570(5) Uani 1 1 d . . . . .
H11 H 0.250312 0.152978 0.199032 0.068 Uiso 1 1 calc R . . . .
C2 C 0.08443(10) 1.1496(4) -0.13836(11) 0.0622(6) Uani 1 1 d . . . . .
H2A H 0.056084 1.028269 -0.130727 0.093 Uiso 1 1 calc GR . . . .
H2B H 0.119031 1.086591 -0.157063 0.093 Uiso 1 1 calc GR . . . .
H2C H 0.061643 1.259109 -0.169341 0.093 Uiso 1 1 calc GR . . . .
C1 C 0.15591(11) 1.4631(4) -0.08001(13) 0.0665(6) Uani 1 1 d . . . . .
H1A H 0.132981 1.581571 -0.107451 0.100 Uiso 1 1 calc GR . . . .
H1B H 0.189526 1.406225 -0.101406 0.100 Uiso 1 1 calc GR . . . .
H1C H 0.173818 1.524827 -0.036467 0.100 Uiso 1 1 calc GR . . . .
C9 C 0.11661(10) 0.3694(5) 0.22201(11) 0.0679(6) Uani 1 1 d . . . . .
H9 H 0.084298 0.345605 0.246669 0.081 Uiso 1 1 calc R . . . .
C10 C 0.16767(11) 0.2224(4) 0.22979(11) 0.0651(6) Uani 1 1 d . . . . .
H10 H 0.169868 0.100832 0.260085 0.078 Uiso 1 1 calc R . . . .
H1 H 0.0357(10) 1.458(4) -0.0497(11) 0.067(7) Uiso 1 1 d . . . . .
H8 H 0.0640(13) 0.805(5) 0.1399(15) 0.105(10) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N3 N2 1.380(2) . ?
N3 C6 1.283(2) . ?
N2 C4 1.376(2) . ?
N2 C5 1.423(2) . ?
O5 C5 1.217(2) . ?
O4 C4 1.212(2) . ?
C7 C6 1.445(3) . ?
C7 C12 1.399(2) . ?
C7 C8 1.400(3) . ?
N1 C5 1.325(2) . ?
N1 C3 1.461(2) . ?
N1 H1 0.85(2) . ?
C4 C3 1.516(3) . ?
O8 C8 1.350(2) . ?
O8 H8 0.93(3) . ?
C6 H6 0.9300 . ?
C12 H12 0.9300 . ?
C12 C11 1.367(3) . ?
C3 C2 1.524(3) . ?
C3 C1 1.518(3) . ?
C8 C9 1.385(3) . ?
C11 H11 0.9300 . ?
C11 C10 1.375(3) . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C9 H9 0.9300 . ?
C9 C10 1.371(3) . ?
C10 H10 0.9300 . ?

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
C6 N3 N2 119.56(15) . . ?
N3 N2 C5 117.92(14) . . ?
C4 N2 N3 130.37(14) . . ?
C4 N2 C5 111.20(15) . . ?
C12 C7 C6 118.91(16) . . ?
C12 C7 C8 117.99(17) . . ?
C8 C7 C6 123.08(16) . . ?
C5 N1 C3 114.06(15) . . ?
C5 N1 H1 122.7(15) . . ?
C3 N1 H1 123.1(15) . . ?
N2 C4 C3 107.03(14) . . ?
O4 C4 N2 126.77(17) . . ?
O4 C4 C3 126.18(17) . . ?
C8 O8 H8 109.4(18) . . ?
N3 C6 C7 120.21(17) . . ?
N3 C6 H6 119.9 . . ?
C7 C6 H6 119.9 . . ?
O5 C5 N2 123.81(17) . . ?
O5 C5 N1 129.70(17) . . ?
N1 C5 N2 106.48(15) . . ?
C7 C12 H12 119.1 . . ?
C11 C12 C7 121.85(18) . . ?
C11 C12 H12 119.1 . . ?
N1 C3 C4 100.93(14) . . ?
N1 C3 C2 111.61(16) . . ?
N1 C3 C1 112.09(16) . . ?
C4 C3 C2 108.23(16) . . ?
C4 C3 C1 111.04(16) . . ?
C1 C3 C2 112.32(17) . . ?
O8 C8 C7 122.30(18) . . ?
O8 C8 C9 118.00(18) . . ?
C9 C8 C7 119.69(18) . . ?
C12 C11 H11 120.4 . . ?
C12 C11 C10 119.15(19) . . ?
C10 C11 H11 120.4 . . ?
C3 C2 H2A 109.5 . . ?
C3 C2 H2B 109.5 . . ?
C3 C2 H2C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C3 C1 H1A 109.5 . . ?
C3 C1 H1B 109.5 . . ?
C3 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C8 C9 H9 119.8 . . ?
C10 C9 C8 120.5(2) . . ?
C10 C9 H9 119.8 . . ?
C11 C10 H10 119.6 . . ?
C9 C10 C11 120.8(2) . . ?
C9 C10 H10 119.6 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C6 H6 O4 0.93 2.23 2.882(2) 126.1 .
C2 H2C O8 0.96 2.63 3.201(3) 118.1 5_575
N1 H1 O5 0.85(2) 2.10(2) 2.940(2) 166(2) 5_585
O8 H8 N3 0.93(3) 1.83(3) 2.635(2) 144(3) .

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
N3 N2 C4 O4 -10.4(3) . . . . ?
N3 N2 C4 C3 168.01(16) . . . . ?
N3 N2 C5 O5 8.1(3) . . . . ?
N3 N2 C5 N1 -172.58(16) . . . . ?
N2 N3 C6 C7 -176.37(15) . . . . ?
N2 C4 C3 N1 5.08(19) . . . . ?
N2 C4 C3 C2 -112.21(17) . . . . ?
N2 C4 C3 C1 124.08(17) . . . . ?
O4 C4 C3 N1 -176.54(19) . . . . ?
O4 C4 C3 C2 66.2(2) . . . . ?
O4 C4 C3 C1 -57.5(2) . . . . ?
C7 C12 C11 C10 0.8(3) . . . . ?
C7 C8 C9 C10 1.5(3) . . . . ?
C4 N2 C5 O5 -179.27(18) . . . . ?
C4 N2 C5 N1 0.1(2) . . . . ?
O8 C8 C9 C10 -179.5(2) . . . . ?
C6 N3 N2 C4 14.4(3) . . . . ?
C6 N3 N2 C5 -174.67(16) . . . . ?
C6 C7 C12 C11 -178.59(18) . . . . ?
C6 C7 C8 O8 -1.6(3) . . . . ?
C6 C7 C8 C9 177.40(19) . . . . ?
C5 N2 C4 O4 178.20(18) . . . . ?
C5 N2 C4 C3 -3.4(2) . . . . ?
C5 N1 C3 C4 -5.5(2) . . . . ?
C5 N1 C3 C2 109.3(2) . . . . ?
C5 N1 C3 C1 -123.7(2) . . . . ?
C12 C7 C6 N3 174.71(17) . . . . ?
C12 C7 C8 O8 179.89(19) . . . . ?
C12 C7 C8 C9 -1.1(3) . . . . ?
C12 C11 C10 C9 -0.4(3) . . . . ?
C3 N1 C5 N2 3.7(2) . . . . ?
C3 N1 C5 O5 -177.1(2) . . . . ?
C8 C7 C6 N3 -3.7(3) . . . . ?
C8 C7 C12 C11 0.0(3) . . . . ?
C8 C9 C10 C11 -0.7(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
####################################################################### 
# 
# 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_exp_459
_database_code_depnum_ccdc_archive 'CCDC 1878317'
_audit_update_record             
;
2018-11-11 deposited with the CCDC.
2019-01-08 downloaded from the CCDC.
;
_audit_creation_date             2018-07-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H11 N3 O2 S'
_chemical_formula_sum            'C10 H11 N3 O2 S'
_chemical_formula_weight         237.28
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y-1/2, z-1/2'

_cell_length_a                   9.7216(3)
_cell_length_b                   10.6601(3)
_cell_length_c                   22.1772(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2298.31(10)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9204
_cell_measurement_temperature    290
_cell_measurement_theta_max      29.0490
_cell_measurement_theta_min      3.8100
_shelx_estimated_absorpt_T_max   0.968
_shelx_estimated_absorpt_T_min   0.923
_exptl_absorpt_coefficient_mu    0.271
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88455
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             992
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0367
_diffrn_reflns_av_unetI/netI     0.0201
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.945
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            23512
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.945
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.473
_diffrn_reflns_theta_min         2.786
_diffrn_ambient_temperature      290.0
_diffrn_detector_area_resol_mean 10.3974
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.945
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -40.00   62.00   1.0000   55.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.3627   57.0000 -180.0000 102

#__ type_ start__ end____ width___ exp.time_
  2 omega  -91.00   30.00   1.0000   55.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.3627  -19.0000  150.0000 121

#__ type_ start__ end____ width___ exp.time_
  3 omega -100.00   77.00   1.0000   55.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.3627    0.0000 -120.0000 177
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2284
_reflns_number_total             3021
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.252
_refine_diff_density_min         -0.477
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.054
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     151
_refine_ls_number_reflns         3021
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0598
_refine_ls_R_factor_gt           0.0434
_refine_ls_restrained_S_all      1.054
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0475P)²+0.8673P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1081
_refine_ls_wR_factor_ref         0.1168
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C10(H10), C9(H9), C8(H8)
2.b Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C), C1(H1A,H1B,H1C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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 0.06158(7) 0.41447(6) 0.26265(2) 0.0702(2) Uani 1 1 d . . . . .
O5 O 0.03361(12) 0.07936(9) 0.42473(5) 0.0410(3) Uani 1 1 d . . . . .
N3 N 0.11363(14) 0.31691(12) 0.38920(5) 0.0396(3) Uani 1 1 d . . . . .
C5 C 0.06767(15) 0.15658(13) 0.46239(6) 0.0334(3) Uani 1 1 d . . . . .
N1 N 0.06009(14) 0.14950(12) 0.52236(5) 0.0377(3) Uani 1 1 d . . . . .
N2 N 0.12557(13) 0.27444(11) 0.44840(5) 0.0359(3) Uani 1 1 d . . . . .
C7 C 0.17606(17) 0.46665(15) 0.31598(6) 0.0404(3) Uani 1 1 d . . . . .
C6 C 0.18917(17) 0.41030(14) 0.37471(7) 0.0387(3) Uani 1 1 d . . . . .
H6 H 0.252689 0.441908 0.402138 0.046 Uiso 1 1 calc R . . . .
C4 C 0.15307(18) 0.34247(15) 0.50020(6) 0.0404(4) Uani 1 1 d . . . . .
O4 O 0.19326(17) 0.44906(12) 0.50280(5) 0.0644(4) Uani 1 1 d . . . . .
C2 C 0.0186(2) 0.31963(18) 0.59546(8) 0.0557(5) Uani 1 1 d . . . . .
H2A H -0.062657 0.342217 0.573374 0.083 Uiso 1 1 calc GR . . . .
H2B H 0.059523 0.393705 0.612307 0.083 Uiso 1 1 calc GR . . . .
H2C H -0.005513 0.262824 0.627346 0.083 Uiso 1 1 calc GR . . . .
C3 C 0.12064(16) 0.25645(14) 0.55322(6) 0.0370(3) Uani 1 1 d . . . . .
C10 C 0.2429(2) 0.57141(17) 0.29676(7) 0.0523(4) Uani 1 1 d . . . . .
H10 H 0.308410 0.613734 0.319587 0.063 Uiso 1 1 calc R . . . .
C1 C 0.2533(2) 0.21925(18) 0.58546(7) 0.0516(4) Uani 1 1 d . . . . .
H1A H 0.232272 0.162797 0.617900 0.077 Uiso 1 1 calc GR . . . .
H1B H 0.297112 0.292944 0.601307 0.077 Uiso 1 1 calc GR . . . .
H1C H 0.314043 0.178645 0.557452 0.077 Uiso 1 1 calc GR . . . .
C9 C 0.2023(3) 0.6087(2) 0.23862(8) 0.0673(6) Uani 1 1 d . . . . .
H9 H 0.237763 0.678424 0.218822 0.081 Uiso 1 1 calc R . . . .
C8 C 0.1074(3) 0.5331(2) 0.21501(9) 0.0745(7) Uani 1 1 d . . . . .
H8 H 0.070209 0.543868 0.176726 0.089 Uiso 1 1 calc R . . . .
H1 H 0.045(2) 0.0780(18) 0.5402(9) 0.050(5) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C7 1.7166(17) . ?
S1 C8 1.708(2) . ?
O5 C5 1.2184(17) . ?
N3 N2 1.3936(16) . ?
N3 C6 1.278(2) . ?
C5 N1 1.3342(18) . ?
C5 N2 1.4113(18) . ?
N1 C3 1.4542(19) . ?
N1 H1 0.87(2) . ?
N2 C4 1.3847(18) . ?
C7 C6 1.440(2) . ?
C7 C10 1.361(2) . ?
C6 H6 0.9300 . ?
C4 O4 1.2029(19) . ?
C4 C3 1.524(2) . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C2 C3 1.522(2) . ?
C3 C1 1.527(2) . ?
C10 H10 0.9300 . ?
C10 C9 1.406(2) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C9 H9 0.9300 . ?
C9 C8 1.331(3) . ?
C8 H8 0.9300 . ?

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
C8 S1 C7 90.98(10) . . ?
C6 N3 N2 116.23(13) . . ?
O5 C5 N1 129.05(14) . . ?
O5 C5 N2 124.00(13) . . ?
N1 C5 N2 106.95(12) . . ?
C5 N1 C3 113.73(12) . . ?
C5 N1 H1 120.7(13) . . ?
C3 N1 H1 122.7(13) . . ?
N3 N2 C5 117.59(11) . . ?
C4 N2 N3 128.87(12) . . ?
C4 N2 C5 111.15(12) . . ?
C6 C7 S1 123.05(12) . . ?
C10 C7 S1 111.09(12) . . ?
C10 C7 C6 125.69(16) . . ?
N3 C6 C7 120.10(14) . . ?
N3 C6 H6 120.0 . . ?
C7 C6 H6 120.0 . . ?
N2 C4 C3 106.56(12) . . ?
O4 C4 N2 126.66(14) . . ?
O4 C4 C3 126.77(13) . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
C3 C2 H2A 109.5 . . ?
C3 C2 H2B 109.5 . . ?
C3 C2 H2C 109.5 . . ?
N1 C3 C4 101.09(11) . . ?
N1 C3 C2 111.89(14) . . ?
N1 C3 C1 111.02(13) . . ?
C4 C3 C1 110.04(13) . . ?
C2 C3 C4 110.09(14) . . ?
C2 C3 C1 112.17(14) . . ?
C7 C10 H10 123.7 . . ?
C7 C10 C9 112.63(18) . . ?
C9 C10 H10 123.7 . . ?
C3 C1 H1A 109.5 . . ?
C3 C1 H1B 109.5 . . ?
C3 C1 H1C 109.5 . . ?
H1A C1 H1B 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C10 C9 H9 123.7 . . ?
C8 C9 C10 112.63(19) . . ?
C8 C9 H9 123.7 . . ?
S1 C8 H8 123.7 . . ?
C9 C8 S1 112.67(15) . . ?
C9 C8 H8 123.7 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C6 H6 O5 0.93 2.59 3.427(2) 149.7 7_665
C6 H6 O4 0.93 2.31 2.8708(19) 118.6 .
C8 H8 O5 0.93 2.49 3.425(2) 178.0 4
N1 H1 O5 0.87(2) 2.00(2) 2.8563(16) 166.9(18) 5_556

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
S1 C7 C6 N3 0.0(2) . . . . ?
S1 C7 C10 C9 -0.5(2) . . . . ?
O5 C5 N1 C3 175.44(15) . . . . ?
O5 C5 N2 N3 15.6(2) . . . . ?
O5 C5 N2 C4 179.61(15) . . . . ?
N3 N2 C4 O4 -12.6(3) . . . . ?
N3 N2 C4 C3 166.67(14) . . . . ?
C5 N1 C3 C4 6.84(17) . . . . ?
C5 N1 C3 C2 123.97(15) . . . . ?
C5 N1 C3 C1 -109.86(15) . . . . ?
C5 N2 C4 O4 -174.36(18) . . . . ?
C5 N2 C4 C3 4.92(17) . . . . ?
N1 C5 N2 N3 -164.73(13) . . . . ?
N1 C5 N2 C4 -0.70(17) . . . . ?
N2 N3 C6 C7 -175.22(13) . . . . ?
N2 C5 N1 C3 -4.23(17) . . . . ?
N2 C4 C3 N1 -6.75(16) . . . . ?
N2 C4 C3 C2 -125.19(15) . . . . ?
N2 C4 C3 C1 110.67(15) . . . . ?
C7 S1 C8 C9 -0.9(2) . . . . ?
C7 C10 C9 C8 -0.1(3) . . . . ?
C6 N3 N2 C5 -166.54(14) . . . . ?
C6 N3 N2 C4 32.7(2) . . . . ?
C6 C7 C10 C9 -175.99(17) . . . . ?
O4 C4 C3 N1 172.52(19) . . . . ?
O4 C4 C3 C2 54.1(2) . . . . ?
O4 C4 C3 C1 -70.1(2) . . . . ?
C10 C7 C6 N3 174.98(17) . . . . ?
C10 C9 C8 S1 0.8(3) . . . . ?
C8 S1 C7 C6 176.40(16) . . . . ?
C8 S1 C7 C10 0.81(16) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
