# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_4503
_audit_block_doi                 10.5517/ccdc.csd.cc1myqcn
_database_code_depnum_ccdc_archive 'CCDC 1518112'
_audit_update_record             
;
2016-11-20 deposited with the CCDC.
2017-12-21 downloaded from the CCDC.
;
_audit_creation_date             2016-09-21
_audit_creation_method           
;
  Olex2 1.1
  (compiled 2011.02.15 svn.r1672, GUI svn.r3494)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C9 H12 Cl N5 O3'
_chemical_formula_sum            'C9 H12 Cl N5 O3'
_chemical_formula_weight         273.69
_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'
Cl Cl 0.1484 0.1585 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x, y+1/2, -z+1/2'
3 '-x, -y, -z'
4 'x, -y-1/2, z-1/2'

_cell_length_a                   11.7756(4)
_cell_length_b                   9.1501(3)
_cell_length_c                   11.4455(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.010(3)
_cell_angle_gamma                90.00
_cell_volume                     1201.57(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1701
_cell_measurement_temperature    105.2
_cell_measurement_theta_max      29.0234
_cell_measurement_theta_min      3.1537
_exptl_absorpt_coefficient_mu    0.328
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94321
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.513
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       ?
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.25
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0201
_diffrn_reflns_av_unetI/netI     0.0351
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            4458
_diffrn_reflns_theta_full        25.99
_diffrn_reflns_theta_max         25.99
_diffrn_reflns_theta_min         3.16
_diffrn_ambient_temperature      105.2
_diffrn_detector_area_resol_mean 16.0971
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega    1.00   83.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       21.1390   77.0000   90.0000 82

#__ type_ start__ end____ width___ exp.time_
  2 omega  -49.00   10.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       21.1390  -77.0000  -30.0000 59

#__ type_ start__ end____ width___ exp.time_
  3 omega    3.00   45.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       21.1390  -37.0000  -60.0000 42

#__ type_ start__ end____ width___ exp.time_
  4 omega    3.00   31.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       21.1390   50.0000 -124.0000 28
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0500146000
_diffrn_orient_matrix_UB_12      -0.0453390000
_diffrn_orient_matrix_UB_13      0.0079964000
_diffrn_orient_matrix_UB_21      0.0043604000
_diffrn_orient_matrix_UB_22      0.0150157000
_diffrn_orient_matrix_UB_23      -0.0596569000
_diffrn_orient_matrix_UB_31      0.0360332000
_diffrn_orient_matrix_UB_32      0.0610629000
_diffrn_orient_matrix_UB_33      0.0205865000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1983
_reflns_number_total             2357
_reflns_odcompleteness_completeness 99.73
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    
'A short history of SHELX (Sheldrick, 2007)/Bruker'
_refine_diff_density_max         0.404
_refine_diff_density_min         -0.493
_refine_diff_density_rms         0.058
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2357
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0497
_refine_ls_R_factor_gt           0.0411
_refine_ls_restrained_S_all      1.067
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0421P)²+0.7261P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0984
_refine_ls_wR_factor_ref         0.1039
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.68769(5) 0.01379(6) 0.45168(6) 0.03369(18) Uani 1 1 d . . .
O1 O 0.24395(12) 0.45213(15) 0.55822(12) 0.0204(3) Uani 1 1 d . . .
O3 O 0.01741(13) 0.05150(17) 0.20087(13) 0.0281(4) Uani 1 1 d . . .
N5 N 0.03475(15) 0.10168(18) 0.30419(15) 0.0213(4) Uani 1 1 d . . .
O2 O -0.02005(14) 0.05423(18) 0.37808(14) 0.0321(4) Uani 1 1 d . . .
N2 N 0.20283(14) 0.39533(18) 0.44229(14) 0.0185(4) Uani 1 1 d . . .
C6 C 0.28068(16) 0.4207(2) 0.36100(17) 0.0190(4) Uani 1 1 d . . .
H6A H 0.3087 0.5207 0.3703 0.023 Uiso 1 1 calc R . .
H6B H 0.2370 0.4088 0.2790 0.023 Uiso 1 1 calc R . .
N4 N 0.11517(14) 0.20928(17) 0.32796(14) 0.0185(4) Uani 1 1 d . . .
C4 C 0.38397(16) 0.3181(2) 0.38352(17) 0.0176(4) Uani 1 1 d . . .
N1 N 0.55910(16) 0.2252(2) 0.51448(16) 0.0280(4) Uani 1 1 d . . .
C1 C 0.56699(17) 0.1311(2) 0.42536(19) 0.0221(4) Uani 1 1 d . . .
N3 N 0.09296(14) 0.24073(19) 0.53152(15) 0.0211(4) Uani 1 1 d . . .
H3A H 0.0483 0.1659 0.5294 0.025 Uiso 1 1 calc R . .
H3B H 0.1114 0.2928 0.5955 0.025 Uiso 1 1 calc R . .
C7 C 0.13325(16) 0.2756(2) 0.43629(17) 0.0175(4) Uani 1 1 d . . .
C5 C 0.46620(17) 0.3182(2) 0.49217(18) 0.0205(4) Uani 1 1 d . . .
H5 H 0.4575 0.3840 0.5515 0.025 Uiso 1 1 calc R . .
C3 C 0.39893(18) 0.2162(2) 0.29829(18) 0.0250(5) Uani 1 1 d . . .
H3 H 0.3444 0.2118 0.2257 0.030 Uiso 1 1 calc R . .
C2 C 0.49115(17) 0.1225(2) 0.31800(18) 0.0210(4) Uani 1 1 d . . .
H2 H 0.5014 0.0555 0.2601 0.025 Uiso 1 1 calc R . .
C8 C 0.19252(18) 0.5957(2) 0.56673(19) 0.0239(5) Uani 1 1 d . . .
H8A H 0.1083 0.5883 0.5525 0.029 Uiso 1 1 calc R . .
H8B H 0.2121 0.6620 0.5081 0.029 Uiso 1 1 calc R . .
C9 C 0.2428(2) 0.6496(2) 0.69220(19) 0.0300(5) Uani 1 1 d . . .
H9A H 0.2112 0.7442 0.7027 0.045 Uiso 1 1 calc R . .
H9B H 0.3260 0.6566 0.7048 0.045 Uiso 1 1 calc R . .
H9C H 0.2233 0.5825 0.7491 0.045 Uiso 1 1 calc R . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cl1 0.0267(3) 0.0259(3) 0.0495(4) 0.0080(3) 0.0107(3) 0.0072(2)
O1 0.0208(7) 0.0223(7) 0.0154(7) -0.0024(6) -0.0015(6) 0.0023(6)
O3 0.0343(9) 0.0336(9) 0.0162(7) -0.0062(7) 0.0050(6) -0.0117(7)
N5 0.0210(9) 0.0222(9) 0.0200(9) 0.0025(8) 0.0034(7) -0.0012(7)
O2 0.0383(9) 0.0380(9) 0.0231(8) -0.0007(7) 0.0136(7) -0.0173(7)
N2 0.0197(8) 0.0217(9) 0.0127(8) -0.0018(7) 0.0006(7) -0.0014(7)
C6 0.0192(10) 0.0215(10) 0.0157(9) 0.0019(8) 0.0025(8) -0.0029(8)
N4 0.0185(8) 0.0192(8) 0.0172(8) -0.0004(7) 0.0029(7) -0.0025(7)
C4 0.0179(9) 0.0166(9) 0.0187(10) 0.0015(8) 0.0048(8) -0.0052(7)
N1 0.0277(10) 0.0313(10) 0.0247(10) 0.0014(8) 0.0056(8) -0.0001(8)
C1 0.0218(10) 0.0181(10) 0.0278(11) 0.0024(9) 0.0083(9) 0.0001(8)
N3 0.0237(9) 0.0229(9) 0.0178(9) -0.0015(7) 0.0069(7) -0.0026(7)
C7 0.0148(9) 0.0196(10) 0.0172(10) 0.0036(8) 0.0017(8) 0.0046(7)
C5 0.0211(10) 0.0202(10) 0.0194(10) -0.0030(8) 0.0028(8) -0.0013(8)
C3 0.0266(11) 0.0296(12) 0.0162(10) -0.0041(9) -0.0005(9) -0.0017(9)
C2 0.0213(10) 0.0213(10) 0.0192(10) -0.0092(9) 0.0020(8) 0.0012(8)
C8 0.0253(11) 0.0206(10) 0.0252(11) -0.0005(9) 0.0048(9) 0.0030(8)
C9 0.0373(13) 0.0280(11) 0.0242(12) -0.0052(10) 0.0058(10) -0.0031(10)

_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 1.752(2) . ?
O1 N2 1.406(2) . ?
O1 C8 1.459(2) . ?
O3 N5 1.242(2) . ?
N5 O2 1.251(2) . ?
N5 N4 1.351(2) . ?
N2 C6 1.464(2) . ?
N2 C7 1.360(2) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C6 C4 1.512(3) . ?
N4 C7 1.354(2) . ?
C4 C5 1.393(3) . ?
C4 C3 1.389(3) . ?
N1 C1 1.354(3) . ?
N1 C5 1.364(3) . ?
C1 C2 1.349(3) . ?
N3 H3A 0.8600 . ?
N3 H3B 0.8600 . ?
N3 C7 1.322(2) . ?
C5 H5 0.9300 . ?
C3 H3 0.9300 . ?
C3 C2 1.362(3) . ?
C2 H2 0.9300 . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.508(3) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?

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
N2 O1 C8 109.63(14) . . ?
O3 N5 O2 121.07(16) . . ?
O3 N5 N4 114.76(16) . . ?
O2 N5 N4 124.17(17) . . ?
O1 N2 C6 114.15(14) . . ?
C7 N2 O1 114.89(15) . . ?
C7 N2 C6 123.50(16) . . ?
N2 C6 H6A 109.0 . . ?
N2 C6 H6B 109.0 . . ?
N2 C6 C4 112.83(16) . . ?
H6A C6 H6B 107.8 . . ?
C4 C6 H6A 109.0 . . ?
C4 C6 H6B 109.0 . . ?
N5 N4 C7 118.03(16) . . ?
C5 C4 C6 121.50(17) . . ?
C3 C4 C6 121.43(17) . . ?
C3 C4 C5 117.03(18) . . ?
C1 N1 C5 116.35(18) . . ?
N1 C1 Cl1 116.78(16) . . ?
C2 C1 Cl1 117.75(16) . . ?
C2 C1 N1 125.46(19) . . ?
H3A N3 H3B 120.0 . . ?
C7 N3 H3A 120.0 . . ?
C7 N3 H3B 120.0 . . ?
N4 C7 N2 112.09(16) . . ?
N3 C7 N2 118.48(18) . . ?
N3 C7 N4 129.43(18) . . ?
C4 C5 H5 118.9 . . ?
N1 C5 C4 122.24(18) . . ?
N1 C5 H5 118.9 . . ?
C4 C3 H3 119.0 . . ?
C2 C3 C4 121.93(19) . . ?
C2 C3 H3 119.0 . . ?
C1 C2 C3 116.97(19) . . ?
C1 C2 H2 121.5 . . ?
C3 C2 H2 121.5 . . ?
O1 C8 H8A 110.5 . . ?
O1 C8 H8B 110.5 . . ?
O1 C8 C9 106.16(16) . . ?
H8A C8 H8B 108.7 . . ?
C9 C8 H8A 110.5 . . ?
C9 C8 H8B 110.5 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 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
Cl1 C1 C2 C3 -178.90(16) . . . . ?
O1 N2 C6 C4 77.4(2) . . . . ?
O1 N2 C7 N4 -167.91(14) . . . . ?
O1 N2 C7 N3 12.6(2) . . . . ?
O3 N5 N4 C7 175.85(16) . . . . ?
N5 N4 C7 N2 -170.83(15) . . . . ?
N5 N4 C7 N3 8.6(3) . . . . ?
O2 N5 N4 C7 -3.8(3) . . . . ?
N2 O1 C8 C9 -178.86(15) . . . . ?
N2 C6 C4 C5 -62.7(2) . . . . ?
N2 C6 C4 C3 115.1(2) . . . . ?
C6 N2 C7 N4 -19.9(2) . . . . ?
C6 N2 C7 N3 160.55(17) . . . . ?
C6 C4 C5 N1 179.17(18) . . . . ?
C6 C4 C3 C2 -179.46(19) . . . . ?
C4 C3 C2 C1 1.1(3) . . . . ?
N1 C1 C2 C3 -0.2(3) . . . . ?
C1 N1 C5 C4 -0.5(3) . . . . ?
C7 N2 C6 C4 -70.8(2) . . . . ?
C5 C4 C3 C2 -1.6(3) . . . . ?
C5 N1 C1 Cl1 178.63(15) . . . . ?
C5 N1 C1 C2 -0.1(3) . . . . ?
C3 C4 C5 N1 1.3(3) . . . . ?
C8 O1 N2 C6 96.07(18) . . . . ?
C8 O1 N2 C7 -112.90(17) . . . . ?

