# 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 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_safin293
_database_code_depnum_ccdc_archive 'CCDC 915012'
_audit_update_record             
;
2012-12-10 deposited with the CCDC.
2017-06-28 downloaded from the CCDC.
;
#TrackingRef 'web_deposit_cif_file_0_Damir_1356601249.1.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C9 H7 N7, C5 H8 N3, H2 O, Cl'
_chemical_formula_sum            'C14 H17 Cl N10 O'
_chemical_formula_weight         376.83

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   10.0312(7)
_cell_length_b                   15.7314(8)
_cell_length_c                   11.0525(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.436(5)
_cell_angle_gamma                90.00
_cell_volume                     1733.14(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3495
_cell_measurement_theta_min      2.8998
_cell_measurement_theta_max      26.0177

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.444
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             784
_exptl_absorpt_coefficient_mu    0.249
_exptl_absorpt_correction_T_min  0.93795
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11648
_diffrn_reflns_av_R_equivalents  0.0740
_diffrn_reflns_av_sigmaI/netI    0.0644
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.91
_diffrn_reflns_theta_max         26.07
_reflns_number_total             3353
_reflns_number_gt                2011
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       MAR
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0476P)²+0.8360P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3353
_refine_ls_number_parameters     244
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1028
_refine_ls_R_factor_gt           0.0538
_refine_ls_wR_factor_ref         0.1462
_refine_ls_wR_factor_gt          0.1166
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.77257(8) 0.05019(4) 0.06347(6) 0.0676(2) Uani 1 1 d . . .
N2 N 0.83851(19) 0.90816(11) 0.54637(17) 0.0424(5) Uani 1 1 d . . .
C3 C 0.8206(2) 0.82457(14) 0.5386(2) 0.0430(6) Uani 1 1 d . . .
C4 C 0.7736(3) 0.78191(16) 0.4333(2) 0.0536(7) Uani 1 1 d . . .
H4 H 0.7623 0.7232 0.4322 0.064 Uiso 1 1 calc R . .
C5 C 0.7441(3) 0.83051(16) 0.3296(2) 0.0571(7) Uani 1 1 d . . .
H5 H 0.7131 0.8045 0.2563 0.069 Uiso 1 1 calc R . .
C6 C 0.7608(3) 0.91800(15) 0.3346(2) 0.0506(7) Uani 1 1 d . . .
H6 H 0.7409 0.9517 0.2659 0.061 Uiso 1 1 calc R . .
C7 C 0.8077(2) 0.95277(14) 0.4447(2) 0.0405(6) Uani 1 1 d . . .
N8 N 0.8536(2) 0.78126(12) 0.65163(17) 0.0467(5) Uani 1 1 d . . .
C9 C 0.8939(3) 0.81720(17) 0.7623(2) 0.0556(7) Uani 1 1 d . . .
H9 H 0.9026 0.8753 0.7762 0.067 Uiso 1 1 calc R . .
N10 N 0.9184(2) 0.75905(14) 0.84550(19) 0.0622(7) Uani 1 1 d . . .
N11 N 0.8962(2) 0.68065(14) 0.78917(19) 0.0632(7) Uani 1 1 d . . .
C12 C 0.8577(3) 0.69632(16) 0.6741(2) 0.0598(8) Uani 1 1 d . . .
H12 H 0.8360 0.6547 0.6154 0.072 Uiso 1 1 calc R . .
N13 N 0.8288(2) 1.04180(11) 0.46144(16) 0.0432(5) Uani 1 1 d . . .
C14 C 0.8226(3) 1.10576(15) 0.3776(2) 0.0514(7) Uani 1 1 d . . .
H14 H 0.8020 1.0980 0.2942 0.062 Uiso 1 1 calc R . .
N15 N 0.8496(2) 1.17974(12) 0.43005(18) 0.0514(6) Uani 1 1 d . . .
N16 N 0.8757(2) 1.16288(13) 0.55413(19) 0.0552(6) Uani 1 1 d . . .
C17 C 0.8620(3) 1.08119(15) 0.5705(2) 0.0499(7) Uani 1 1 d . . .
H17 H 0.8733 1.0539 0.6456 0.060 Uiso 1 1 calc R . .
N21 N 0.9405(2) 0.30261(12) 0.71018(17) 0.0490(6) Uani 1 1 d . . .
H21 H 0.924(2) 0.2443(15) 0.665(2) 0.059 Uiso 1 1 d . . .
C22 C 0.9108(3) 0.37589(16) 0.6470(2) 0.0543(7) Uani 1 1 d . . .
C23 C 0.9229(3) 0.45281(16) 0.7085(3) 0.0623(8) Uani 1 1 d . . .
H23 H 0.9031 0.5038 0.6677 0.075 Uiso 1 1 calc R . .
C24 C 0.9648(3) 0.45179(17) 0.8313(2) 0.0604(8) Uani 1 1 d . . .
H24 H 0.9731 0.5032 0.8730 0.073 Uiso 1 1 calc R . .
C25 C 0.9949(3) 0.37829(16) 0.8945(2) 0.0552(7) Uani 1 1 d . . .
H25 H 1.0235 0.3797 0.9774 0.066 Uiso 1 1 calc R . .
C26 C 0.9819(3) 0.30139(15) 0.8321(2) 0.0481(7) Uani 1 1 d . . .
N27 N 0.8715(3) 0.36855(15) 0.5268(2) 0.0783(8) Uani 1 1 d . . .
H27A H 0.8662 0.3192 0.4933 0.094 Uiso 1 1 calc R . .
H27B H 0.8519 0.4133 0.4837 0.094 Uiso 1 1 calc R . .
N28 N 1.0063(2) 0.22581(14) 0.88550(19) 0.0661(7) Uani 1 1 d . . .
H28A H 0.9958 0.1800 0.8431 0.079 Uiso 1 1 calc R . .
H28B H 1.0325 0.2231 0.9622 0.079 Uiso 1 1 calc R . .
O31 O 0.9513(2) 0.03939(14) 0.84137(17) 0.0794(7) Uani 1 1 d . . .
H31A H 1.030(3) 0.017(2) 0.873(3) 0.095 Uiso 1 1 d . . .
H31B H 0.901(3) 0.0385(19) 0.905(3) 0.095 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
N2 C3 1.329(3) . ?
N2 C7 1.332(3) . ?
C3 C4 1.379(3) . ?
C3 N8 1.429(3) . ?
C4 C5 1.382(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.387(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.368(3) . ?
C6 H6 0.9300 . ?
C7 N13 1.425(3) . ?
N8 C12 1.359(3) . ?
N8 C9 1.367(3) . ?
C9 N10 1.301(3) . ?
C9 H9 0.9300 . ?
N10 N11 1.388(3) . ?
N11 C12 1.311(3) . ?
C12 H12 0.9300 . ?
N13 C17 1.363(3) . ?
N13 C14 1.364(3) . ?
C14 N15 1.315(3) . ?
C14 H14 0.9300 . ?
N15 N16 1.393(3) . ?
N16 C17 1.307(3) . ?
C17 H17 0.9300 . ?
N21 C22 1.363(3) . ?
N21 C26 1.365(3) . ?
N21 H21 1.05(2) . ?
C22 N27 1.347(3) . ?
C22 C23 1.386(3) . ?
C23 C24 1.376(4) . ?
C23 H23 0.9300 . ?
C24 C25 1.367(4) . ?
C24 H24 0.9300 . ?
C25 C26 1.391(3) . ?
C25 H25 0.9300 . ?
C26 N28 1.338(3) . ?
N27 H27A 0.8600 . ?
N27 H27B 0.8600 . ?
N28 H28A 0.8600 . ?
N28 H28B 0.8600 . ?
O31 H31A 0.90(3) . ?
O31 H31B 0.91(3) . ?

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 N2 C7 116.73(19) . . ?
N2 C3 C4 124.6(2) . . ?
N2 C3 N8 113.50(19) . . ?
C4 C3 N8 121.9(2) . . ?
C3 C4 C5 116.8(2) . . ?
C3 C4 H4 121.6 . . ?
C5 C4 H4 121.6 . . ?
C4 C5 C6 120.2(2) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C7 C6 C5 117.4(2) . . ?
C7 C6 H6 121.3 . . ?
C5 C6 H6 121.3 . . ?
N2 C7 C6 124.3(2) . . ?
N2 C7 N13 113.02(18) . . ?
C6 C7 N13 122.7(2) . . ?
C12 N8 C9 104.1(2) . . ?
C12 N8 C3 128.9(2) . . ?
C9 N8 C3 126.97(19) . . ?
N10 C9 N8 110.8(2) . . ?
N10 C9 H9 124.6 . . ?
N8 C9 H9 124.6 . . ?
C9 N10 N11 107.4(2) . . ?
C12 N11 N10 106.4(2) . . ?
N11 C12 N8 111.2(2) . . ?
N11 C12 H12 124.4 . . ?
N8 C12 H12 124.4 . . ?
C17 N13 C14 104.67(19) . . ?
C17 N13 C7 125.42(18) . . ?
C14 N13 C7 129.91(19) . . ?
N15 C14 N13 111.2(2) . . ?
N15 C14 H14 124.4 . . ?
N13 C14 H14 124.4 . . ?
C14 N15 N16 105.78(19) . . ?
C17 N16 N15 108.22(19) . . ?
N16 C17 N13 110.1(2) . . ?
N16 C17 H17 125.0 . . ?
N13 C17 H17 125.0 . . ?
C22 N21 C26 122.9(2) . . ?
C22 N21 H21 118.7(13) . . ?
C26 N21 H21 118.3(13) . . ?
N27 C22 N21 117.1(2) . . ?
N27 C22 C23 123.9(2) . . ?
N21 C22 C23 119.0(2) . . ?
C24 C23 C22 118.3(2) . . ?
C24 C23 H23 120.9 . . ?
C22 C23 H23 120.9 . . ?
C25 C24 C23 122.7(2) . . ?
C25 C24 H24 118.7 . . ?
C23 C24 H24 118.7 . . ?
C24 C25 C26 118.7(2) . . ?
C24 C25 H25 120.7 . . ?
C26 C25 H25 120.7 . . ?
N28 C26 N21 117.9(2) . . ?
N28 C26 C25 123.5(2) . . ?
N21 C26 C25 118.6(2) . . ?
C22 N27 H27A 120.0 . . ?
C22 N27 H27B 120.0 . . ?
H27A N27 H27B 120.0 . . ?
C26 N28 H28A 120.0 . . ?
C26 N28 H28B 120.0 . . ?
H28A N28 H28B 120.0 . . ?
H31A O31 H31B 104(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
C7 N2 C3 C4 0.4(4) . . . . ?
C7 N2 C3 N8 -179.0(2) . . . . ?
N2 C3 C4 C5 0.3(4) . . . . ?
N8 C3 C4 C5 179.5(2) . . . . ?
C3 C4 C5 C6 -0.7(4) . . . . ?
C4 C5 C6 C7 0.4(4) . . . . ?
C3 N2 C7 C6 -0.6(4) . . . . ?
C3 N2 C7 N13 179.5(2) . . . . ?
C5 C6 C7 N2 0.2(4) . . . . ?
C5 C6 C7 N13 -179.9(2) . . . . ?
N2 C3 N8 C12 -174.0(2) . . . . ?
C4 C3 N8 C12 6.6(4) . . . . ?
N2 C3 N8 C9 3.1(4) . . . . ?
C4 C3 N8 C9 -176.3(3) . . . . ?
C12 N8 C9 N10 -0.9(3) . . . . ?
C3 N8 C9 N10 -178.6(2) . . . . ?
N8 C9 N10 N11 1.0(3) . . . . ?
C9 N10 N11 C12 -0.6(3) . . . . ?
N10 N11 C12 N8 0.1(3) . . . . ?
C9 N8 C12 N11 0.5(3) . . . . ?
C3 N8 C12 N11 178.1(2) . . . . ?
N2 C7 N13 C17 -7.2(3) . . . . ?
C6 C7 N13 C17 172.9(2) . . . . ?
N2 C7 N13 C14 172.1(2) . . . . ?
C6 C7 N13 C14 -7.7(4) . . . . ?
C17 N13 C14 N15 -0.1(3) . . . . ?
C7 N13 C14 N15 -179.6(2) . . . . ?
N13 C14 N15 N16 0.5(3) . . . . ?
C14 N15 N16 C17 -0.7(3) . . . . ?
N15 N16 C17 N13 0.6(3) . . . . ?
C14 N13 C17 N16 -0.3(3) . . . . ?
C7 N13 C17 N16 179.2(2) . . . . ?
C26 N21 C22 N27 179.7(3) . . . . ?
C26 N21 C22 C23 0.0(4) . . . . ?
N27 C22 C23 C24 -179.5(3) . . . . ?
N21 C22 C23 C24 0.1(4) . . . . ?
C22 C23 C24 C25 0.0(5) . . . . ?
C23 C24 C25 C26 -0.3(4) . . . . ?
C22 N21 C26 N28 178.9(2) . . . . ?
C22 N21 C26 C25 -0.3(4) . . . . ?
C24 C25 C26 N28 -178.7(3) . . . . ?
C24 C25 C26 N21 0.4(4) . . . . ?

_diffrn_measured_fraction_theta_max 0.975
_diffrn_reflns_theta_full        25.24
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.224
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.049


