# 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 2016

####################################################################### 
# 
# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1032819'
_audit_update_record             
;
2014-11-05 deposited with the CCDC.
2016-01-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        'Pyridazine hydrazine compound'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H18 Cl N5 O'
_chemical_formula_sum            'C15 H18 Cl N5 O'
_chemical_formula_weight         319.79

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   P21/n

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                   6.7997(5)
_cell_length_b                   9.5387(8)
_cell_length_c                   24.3565(19)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.512(8)
_cell_angle_gamma                90.00
_cell_volume                     1572.5(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3923
_cell_measurement_theta_min      2.29
_cell_measurement_theta_max      25.96

_exptl_crystal_description       block
_exptl_crystal_colour            brown
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             672
_exptl_absorpt_coefficient_mu    0.252
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9129
_exptl_absorpt_correction_T_max  0.9593
_exptl_absorpt_process_details   'SADABS (Bruker, 2004)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(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  'Bruker axs kappa apex2 CCD Diffractometer'
_diffrn_measurement_method       'ω and φ scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            22501
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.1150
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         2.29
_diffrn_reflns_theta_max         24.99
_reflns_number_total             22501
_reflns_number_gt                12606
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_cell_refinement       'APEX2/SAINT (Bruker, 2004)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2004)'
_computing_structure_solution    'SIR92 (Altornare et al., 1993)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'

_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)+(0.0263P)²+6.3791P] 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         22501
_refine_ls_number_parameters     205
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1530
_refine_ls_R_factor_gt           0.0873
_refine_ls_wR_factor_ref         0.2150
_refine_ls_wR_factor_gt          0.1891
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_restrained_S_all      1.085
_refine_ls_shift/su_max          0.002
_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
C1 C 0.5545(4) 0.1028(3) 0.56805(10) 0.0380(7) Uani 1 1 d . . .
C2 C 0.5374(4) 0.2386(3) 0.54801(11) 0.0440(7) Uani 1 1 d . . .
H2 H 0.6413 0.3020 0.5538 0.053 Uiso 1 1 calc R . .
C3 C 0.3628(4) 0.2762(3) 0.51942(10) 0.0390(7) Uani 1 1 d . . .
H3 H 0.3418 0.3658 0.5050 0.047 Uiso 1 1 calc R . .
C4 C 0.2161(4) 0.1714(3) 0.51293(10) 0.0362(7) Uani 1 1 d . . .
C5 C -0.1782(4) 0.3231(3) 0.42949(10) 0.0391(7) Uani 1 1 d . . .
H5 H -0.2671 0.2504 0.4332 0.047 Uiso 1 1 calc R . .
C6 C -0.2384(4) 0.4412(3) 0.39471(10) 0.0341(6) Uani 1 1 d . . .
C7 C -0.4335(4) 0.4496(3) 0.37064(10) 0.0427(7) Uani 1 1 d . . .
H7 H -0.5225 0.3794 0.3777 0.051 Uiso 1 1 calc R . .
C8 C -0.4971(4) 0.5605(3) 0.33636(10) 0.0415(7) Uani 1 1 d . . .
H8 H -0.6282 0.5646 0.3215 0.050 Uiso 1 1 calc R . .
C9 C -0.3668(4) 0.6646(3) 0.32416(10) 0.0389(7) Uani 1 1 d . . .
C10 C -0.1720(4) 0.6589(3) 0.34847(10) 0.0394(7) Uani 1 1 d . . .
H10 H -0.0834 0.7293 0.3412 0.047 Uiso 1 1 calc R . .
C11 C -0.1101(4) 0.5491(3) 0.38327(10) 0.0362(6) Uani 1 1 d . . .
C12 C -0.6358(4) 0.7946(3) 0.26975(12) 0.0590(9) Uani 1 1 d U . .
H12A H -0.6628 0.8943 0.2665 0.071 Uiso 1 1 calc R . .
H12B H -0.7164 0.7567 0.2970 0.071 Uiso 1 1 calc R . .
C13 C -0.6924(5) 0.7251(3) 0.21503(12) 0.0799(12) Uani 1 1 d U . .
H13A H -0.8300 0.7413 0.2042 0.120 Uiso 1 1 calc R . .
H13B H -0.6684 0.6262 0.2183 0.120 Uiso 1 1 calc R . .
H13C H -0.6148 0.7637 0.1878 0.120 Uiso 1 1 calc R . .
C14 C -0.2913(5) 0.8779(3) 0.27080(11) 0.0559(9) Uani 1 1 d . . .
H14A H -0.3393 0.9097 0.2341 0.067 Uiso 1 1 calc R . .
H14B H -0.1633 0.8345 0.2685 0.067 Uiso 1 1 calc R . .
C15 C -0.2667(5) 1.0038(3) 0.30912(13) 0.0731(10) Uani 1 1 d . . .
H15A H -0.1758 1.0690 0.2953 0.110 Uiso 1 1 calc R . .
H15B H -0.2163 0.9733 0.3453 0.110 Uiso 1 1 calc R . .
H15C H -0.3924 1.0485 0.3109 0.110 Uiso 1 1 calc R . .
N1 N -0.4268(3) 0.7740(2) 0.28880(9) 0.0478(6) Uani 1 1 d . . .
N2 N -0.0038(3) 0.3161(2) 0.45549(9) 0.0399(6) Uani 1 1 d . . .
N3 N 0.0330(3) 0.1957(2) 0.48672(10) 0.0438(6) Uani 1 1 d D . .
N4 N 0.2413(3) 0.0424(2) 0.53340(8) 0.0393(6) Uani 1 1 d . . .
N5 N 0.4156(3) 0.0078(2) 0.56132(8) 0.0374(6) Uani 1 1 d . . .
O1 O 0.0820(3) 0.5503(2) 0.40492(8) 0.0575(6) Uani 1 1 d . . .
H1 H 0.1023 0.4836 0.4259 0.050(10) Uiso 1 1 calc R . .
Cl1 Cl 0.77269(11) 0.04715(8) 0.60381(3) 0.0584(2) Uani 1 1 d . . .
H3A H -0.041(3) 0.1193(18) 0.4756(9) 0.036(7) Uiso 1 1 d 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
C1 N5 1.308(3) . ?
C1 C2 1.385(3) . ?
C1 Cl1 1.730(3) . ?
C2 C3 1.365(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.411(3) . ?
C3 H3 0.9300 . ?
C4 N4 1.332(3) . ?
C4 N3 1.364(3) . ?
C5 N2 1.292(3) . ?
C5 C6 1.445(3) . ?
C5 H5 0.9300 . ?
C6 C11 1.394(3) . ?
C6 C7 1.400(3) . ?
C7 C8 1.391(3) . ?
C7 H7 0.9300 . ?
C8 C9 1.382(3) . ?
C8 H8 0.9300 . ?
C9 N1 1.389(3) . ?
C9 C10 1.399(3) . ?
C10 C11 1.387(3) . ?
C10 H10 0.9300 . ?
C11 O1 1.361(3) . ?
C12 N1 1.465(3) . ?
C12 C13 1.505(4) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 N1 1.449(3) . ?
C14 C15 1.520(4) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
N2 N3 1.387(3) . ?
N3 H3A 0.913(15) . ?
N4 N5 1.350(3) . ?
O1 H1 0.8200 . ?

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
N5 C1 C2 124.7(2) . . ?
N5 C1 Cl1 115.1(2) . . ?
C2 C1 Cl1 120.2(2) . . ?
C3 C2 C1 117.7(2) . . ?
C3 C2 H2 121.2 . . ?
C1 C2 H2 121.2 . . ?
C2 C3 C4 116.2(2) . . ?
C2 C3 H3 121.9 . . ?
C4 C3 H3 121.9 . . ?
N4 C4 N3 114.3(2) . . ?
N4 C4 C3 123.3(2) . . ?
N3 C4 C3 122.4(2) . . ?
N2 C5 C6 121.5(2) . . ?
N2 C5 H5 119.2 . . ?
C6 C5 H5 119.2 . . ?
C11 C6 C7 117.4(2) . . ?
C11 C6 C5 123.0(2) . . ?
C7 C6 C5 119.6(2) . . ?
C8 C7 C6 121.5(3) . . ?
C8 C7 H7 119.3 . . ?
C6 C7 H7 119.3 . . ?
C9 C8 C7 120.4(3) . . ?
C9 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?
C8 C9 N1 121.1(2) . . ?
C8 C9 C10 118.8(2) . . ?
N1 C9 C10 120.1(2) . . ?
C11 C10 C9 120.5(3) . . ?
C11 C10 H10 119.7 . . ?
C9 C10 H10 119.8 . . ?
O1 C11 C10 117.0(2) . . ?
O1 C11 C6 121.6(2) . . ?
C10 C11 C6 121.3(2) . . ?
N1 C12 C13 112.3(3) . . ?
N1 C12 H12A 109.1 . . ?
C13 C12 H12A 109.1 . . ?
N1 C12 H12B 109.1 . . ?
C13 C12 H12B 109.1 . . ?
H12A C12 H12B 107.9 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N1 C14 C15 113.0(2) . . ?
N1 C14 H14A 109.0 . . ?
C15 C14 H14A 109.0 . . ?
N1 C14 H14B 109.0 . . ?
C15 C14 H14B 109.0 . . ?
H14A C14 H14B 107.8 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C9 N1 C14 122.9(2) . . ?
C9 N1 C12 121.0(2) . . ?
C14 N1 C12 116.0(2) . . ?
C5 N2 N3 114.8(2) . . ?
C4 N3 N2 120.4(2) . . ?
C4 N3 H3A 117.1(14) . . ?
N2 N3 H3A 115.7(14) . . ?
C4 N4 N5 119.3(2) . . ?
C1 N5 N4 118.8(2) . . ?
C11 O1 H1 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
N5 C1 C2 C3 0.3(4) . . . . ?
Cl1 C1 C2 C3 179.1(2) . . . . ?
C1 C2 C3 C4 -0.3(4) . . . . ?
C2 C3 C4 N4 0.5(4) . . . . ?
C2 C3 C4 N3 178.0(3) . . . . ?
N2 C5 C6 C11 5.3(4) . . . . ?
N2 C5 C6 C7 -175.2(3) . . . . ?
C11 C6 C7 C8 0.4(4) . . . . ?
C5 C6 C7 C8 -179.2(2) . . . . ?
C6 C7 C8 C9 1.4(4) . . . . ?
C7 C8 C9 N1 178.2(2) . . . . ?
C7 C8 C9 C10 -2.3(4) . . . . ?
C8 C9 C10 C11 1.3(4) . . . . ?
N1 C9 C10 C11 -179.2(2) . . . . ?
C9 C10 C11 O1 179.4(2) . . . . ?
C9 C10 C11 C6 0.5(4) . . . . ?
C7 C6 C11 O1 179.8(2) . . . . ?
C5 C6 C11 O1 -0.6(4) . . . . ?
C7 C6 C11 C10 -1.4(4) . . . . ?
C5 C6 C11 C10 178.2(2) . . . . ?
C8 C9 N1 C14 -174.0(3) . . . . ?
C10 C9 N1 C14 6.5(4) . . . . ?
C8 C9 N1 C12 9.2(4) . . . . ?
C10 C9 N1 C12 -170.3(3) . . . . ?
C15 C14 N1 C9 -89.4(3) . . . . ?
C15 C14 N1 C12 87.5(3) . . . . ?
C13 C12 N1 C9 -94.2(3) . . . . ?
C13 C12 N1 C14 88.8(3) . . . . ?
C6 C5 N2 N3 -179.3(2) . . . . ?
N4 C4 N3 N2 -169.0(2) . . . . ?
C3 C4 N3 N2 13.3(4) . . . . ?
C5 N2 N3 C4 175.3(3) . . . . ?
N3 C4 N4 N5 -178.5(2) . . . . ?
C3 C4 N4 N5 -0.8(4) . . . . ?
C2 C1 N5 N4 -0.6(4) . . . . ?
Cl1 C1 N5 N4 -179.42(17) . . . . ?
C4 N4 N5 C1 0.8(3) . . . . ?

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
C2 H2 O1 0.93 2.48 3.390(3) 164.7 3_666
C5 H5 N5 0.93 2.67 3.562(3) 160.9 3_556
O1 H1 N2 0.82 1.92 2.643(3) 146.3 .
N3 H3A N4 0.913(15) 2.054(16) 2.950(3) 167(2) 3_556

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.341
_refine_diff_density_min         -0.409
_refine_diff_density_rms         0.098
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: DMSO'
