# 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_NWR151-064
_database_code_depnum_ccdc_archive 'CCDC 1834905'
_audit_update_record             
;
2018-04-05 deposited with the CCDC.
2018-06-13 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C9 H9 Cl N4 O3'
_chemical_formula_moiety         'C9 H9 Cl N4 O3'
_chemical_formula_weight         256.65
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
_space_group_IT_number           14
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 1/2-X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 -1/2+X,-1/2-Y,-1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   7.3141(9)
_cell_length_b                   15.4030(17)
_cell_length_c                   10.0589(10)
_cell_angle_alpha                90.0000
_cell_angle_beta                 107.288(8)
_cell_angle_gamma                90.0000
_cell_volume                     1082.0(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8266
_cell_measurement_theta_min      3.06
_cell_measurement_theta_max      27.45
_cell_measurement_temperature    143
#------------------------------------------------------------------------------
_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.200
_exptl_crystal_density_diffrn    1.575
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             528.00
_exptl_absorpt_coefficient_mu    0.356
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.759
_exptl_absorpt_correction_T_max  0.931

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      143
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            10253
_diffrn_reflns_av_unetI/netI     0.0552
_diffrn_reflns_av_R_equivalents  0.0537
_diffrn_reflns_theta_max         27.449
_diffrn_reflns_theta_min         3.055
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             2458
_reflns_number_gt                2082
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0445
_refine_ls_R_factor_gt           0.0343
_refine_ls_wR_factor_ref         0.0847
_refine_ls_wR_factor_gt          0.0809
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         2458
_refine_ls_number_parameters     154
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0445P)²+0.2444P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.30
_refine_diff_density_min         -0.23
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
Cl Cl 0.1484 0.1585
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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
Cl1 Cl 0.31386(6) 0.25662(2) 0.24862(5) 0.03152(13) Uani 1 1 d . . . . .
O1 O -0.10570(14) 0.47753(6) 0.35096(10) 0.0206(2) Uani 1 1 d . . . . .
O2 O 0.55394(15) 0.58622(7) 0.42967(9) 0.0257(2) Uani 1 1 d . . . . .
O3 O 0.22086(17) 0.55845(8) -0.02462(10) 0.0324(3) Uani 1 1 d . . . . .
N1 N 0.34648(17) 0.42281(7) 0.22240(12) 0.0194(3) Uani 1 1 d . . . . .
N2 N 0.13426(17) 0.52535(7) 0.27426(11) 0.0186(2) Uani 1 1 d . . . . .
N3 N 0.08900(17) 0.37357(7) 0.30166(12) 0.0184(2) Uani 1 1 d . . . . .
N4 N 0.39642(17) 0.57065(7) 0.20064(11) 0.0178(2) Uani 1 1 d . . . . .
C1 C 0.2409(2) 0.36297(9) 0.25845(14) 0.0192(3) Uani 1 1 d . . . . .
C2 C 0.28326(19) 0.50287(8) 0.23426(12) 0.0168(3) Uani 1 1 d . . . . .
C3 C 0.04214(19) 0.45707(9) 0.30725(13) 0.0171(3) Uani 1 1 d . . . . .
C4 C -0.2019(2) 0.40659(10) 0.39740(14) 0.0221(3) Uani 1 1 d . . . . .
H4A H -0.308456 0.429486 0.427164 0.026 Uiso 1 1 calc R U . . .
H4B H -0.251125 0.365483 0.320716 0.026 Uiso 1 1 calc R U . . .
H4C H -0.111070 0.376848 0.475693 0.026 Uiso 1 1 calc R U . . .
C5 C 0.5423(2) 0.60674(9) 0.31130(14) 0.0183(3) Uani 1 1 d . . . . .
C6 C 0.6752(2) 0.66939(9) 0.27247(14) 0.0225(3) Uani 1 1 d . . . . .
H6A H 0.806144 0.660988 0.336285 0.027 Uiso 1 1 calc R U . . .
H6B H 0.634982 0.729353 0.285561 0.027 Uiso 1 1 calc R U . . .
C7 C 0.6804(2) 0.65913(10) 0.12298(15) 0.0242(3) Uani 1 1 d . . . . .
H7A H 0.757730 0.706234 0.099687 0.029 Uiso 1 1 calc R U . . .
H7B H 0.739810 0.602880 0.112034 0.029 Uiso 1 1 calc R U . . .
C8 C 0.4766(2) 0.66286(10) 0.02610(14) 0.0229(3) Uani 1 1 d . . . . .
H8A H 0.421148 0.720577 0.033979 0.028 Uiso 1 1 calc R U . . .
H8B H 0.478629 0.655591 -0.071233 0.028 Uiso 1 1 calc R U . . .
C9 C 0.3527(2) 0.59399(9) 0.05939(13) 0.0200(3) Uani 1 1 d . . . . .


#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'SIR2011 (Burla, et al., 2012)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.3 (Rigaku, 2018)'
_computing_molecular_graphics    'CrystalStructure 4.3'

#==============================================================================
# MOLECULAR GEOMETRY

_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
Cl1 C1 1.7348(14) . ?
O1 C3 1.3208(17) . ?
O1 C4 1.4499(17) . ?
O2 C5 1.2102(17) . ?
O3 C9 1.2081(18) . ?
N1 C1 1.3207(18) . ?
N1 C2 1.3348(17) . ?
N2 C2 1.3153(18) . ?
N2 C3 1.3428(18) . ?
N3 C1 1.3176(19) . ?
N3 C3 1.3365(17) . ?
N4 C9 1.4073(17) . ?
N4 C5 1.4073(17) . ?
N4 C2 1.4337(17) . ?
C4 H4A 0.9800 . ?
C4 H4B 0.9800 . ?
C4 H4C 0.9800 . ?
C5 C6 1.5018(19) . ?
C6 C7 1.5236(19) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 C8 1.521(2) . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C8 C9 1.496(2) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?

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
C3 O1 C4 116.81(11) . . ?
C1 N1 C2 111.95(12) . . ?
C2 N2 C3 113.05(12) . . ?
C1 N3 C3 112.64(12) . . ?
C9 N4 C5 126.09(12) . . ?
C9 N4 C2 116.77(11) . . ?
C5 N4 C2 117.14(10) . . ?
N3 C1 N1 128.56(13) . . ?
N3 C1 Cl1 116.08(10) . . ?
N1 C1 Cl1 115.36(11) . . ?
N2 C2 N1 127.67(13) . . ?
N2 C2 N4 117.99(11) . . ?
N1 C2 N4 114.33(12) . . ?
O1 C3 N3 119.28(12) . . ?
O1 C3 N2 114.58(12) . . ?
N3 C3 N2 126.13(13) . . ?
O1 C4 H4A 109.5 . . ?
O1 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
O1 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
O2 C5 N4 119.36(13) . . ?
O2 C5 C6 124.19(12) . . ?
N4 C5 C6 116.45(11) . . ?
C5 C6 C7 113.44(12) . . ?
C5 C6 H6A 108.9 . . ?
C7 C6 H6A 108.9 . . ?
C5 C6 H6B 108.9 . . ?
C7 C6 H6B 108.9 . . ?
H6A C6 H6B 107.7 . . ?
C8 C7 C6 108.76(12) . . ?
C8 C7 H7A 109.9 . . ?
C6 C7 H7A 109.9 . . ?
C8 C7 H7B 109.9 . . ?
C6 C7 H7B 109.9 . . ?
H7A C7 H7B 108.3 . . ?
C9 C8 C7 111.92(12) . . ?
C9 C8 H8A 109.2 . . ?
C7 C8 H8A 109.2 . . ?
C9 C8 H8B 109.2 . . ?
C7 C8 H8B 109.2 . . ?
H8A C8 H8B 107.9 . . ?
O3 C9 N4 119.01(13) . . ?
O3 C9 C8 125.12(12) . . ?
N4 C9 C8 115.86(12) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 N3 C1 N1 0.2(2) . . . . ?
C3 N3 C1 Cl1 179.65(9) . . . . ?
C2 N1 C1 N3 0.2(2) . . . . ?
C2 N1 C1 Cl1 -179.20(9) . . . . ?
C3 N2 C2 N1 0.88(19) . . . . ?
C3 N2 C2 N4 -178.05(10) . . . . ?
C1 N1 C2 N2 -0.85(19) . . . . ?
C1 N1 C2 N4 178.11(10) . . . . ?
C9 N4 C2 N2 -95.10(14) . . . . ?
C5 N4 C2 N2 85.78(15) . . . . ?
C9 N4 C2 N1 85.83(14) . . . . ?
C5 N4 C2 N1 -93.29(14) . . . . ?
C4 O1 C3 N3 3.18(17) . . . . ?
C4 O1 C3 N2 -175.72(11) . . . . ?
C1 N3 C3 O1 -178.94(11) . . . . ?
C1 N3 C3 N2 -0.19(19) . . . . ?
C2 N2 C3 O1 178.51(11) . . . . ?
C2 N2 C3 N3 -0.30(18) . . . . ?
C9 N4 C5 O2 173.51(13) . . . . ?
C2 N4 C5 O2 -7.46(18) . . . . ?
C9 N4 C5 C6 -6.6(2) . . . . ?
C2 N4 C5 C6 172.47(12) . . . . ?
O2 C5 C6 C7 158.31(14) . . . . ?
N4 C5 C6 C7 -21.62(18) . . . . ?
C5 C6 C7 C8 52.87(16) . . . . ?
C6 C7 C8 C9 -58.30(16) . . . . ?
C5 N4 C9 O3 -178.75(13) . . . . ?
C2 N4 C9 O3 2.22(19) . . . . ?
C5 N4 C9 C8 0.9(2) . . . . ?
C2 N4 C9 C8 -178.14(12) . . . . ?
C7 C8 C9 O3 -147.98(15) . . . . ?
C7 C8 C9 N4 32.41(17) . . . . ?


#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.


