# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_con84p2
_database_code_depnum_ccdc_archive 'CCDC 1062218'
_audit_update_record             
;
2015-04-28 deposited with the CCDC.
2015-09-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL
_chemical_name_systematic        
1-[(3-phenylprop-2-en-1-ylidene)hydrazinylidene]-1,2-dihydrophthalazine
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H14 N4'
_chemical_formula_sum            'C17 H14 N4'
_chemical_formula_weight         274.32

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 '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/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

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

_cell_length_a                   15.1030(7)
_cell_length_b                   3.9130(3)
_cell_length_c                   23.4694(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.363(9)
_cell_angle_gamma                90.00
_cell_volume                     1359.81(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    100.0(1)
_cell_measurement_reflns_used    1004
_cell_measurement_theta_min      2
_cell_measurement_theta_max      50

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.098
_exptl_crystal_size_mid          0.035
_exptl_crystal_size_min          0.034
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.340
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             576
_exptl_absorpt_coefficient_mu    0.656
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2003)'
_exptl_absorpt_correction_T_min  0.968
_exptl_absorpt_correction_T_max  0.985
_exptl_special_details           ?

_diffrn_ambient_temperature      100.0(1)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         '30W microsource with MonoCap capillary'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEXII CCD area-detector'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 12.8
_diffrn_standards_number         11
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  11.33
_diffrn_standards_decay_%        0.00
_diffrn_reflns_number            14244
_diffrn_reflns_av_R_equivalents  0.0173
_diffrn_reflns_av_sigmaI/netI    0.0124
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         2.98
_diffrn_reflns_theta_max         72.33
_reflns_number_total             2681
_reflns_number_gt                2610
_reflns_threshold_expression     >2sigma(I)

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

_computing_data_collection       'APEX2 (Bruker, 2010)'
_computing_cell_refinement       'SAINT-Plus (Bruker, 2009)'
_computing_data_reduction        'SAINT-Plus (Bruker, 2009)'
_computing_structure_solution    'SHELXS (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2008)'
_computing_molecular_graphics    
;XP in SHELXTL/PC (Sheldrick, 2008)
 ORTEP-3 W v. 1.062 (Farrugia 2012)
;
_computing_publication_material  
;SHELXL (Sheldrick, 2008) and
 PLATON (Spek, 2009)
;

_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     
'w=1/[σ²(Fo²)+(0.0499P)²+0.4562P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2681
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0339
_refine_ls_R_factor_gt           0.0333
_refine_ls_wR_factor_ref         0.0920
_refine_ls_wR_factor_gt          0.0910
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.001
_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
N1 N 0.41852(5) 0.7750(2) 0.51813(3) 0.0199(2) Uani 1 1 d . . .
H1N H 0.4764 0.8208 0.5389 0.024 Uiso 1 1 d R . .
N2 N 0.40153(5) 0.8986(2) 0.46299(3) 0.0215(2) Uani 1 1 d . . .
C1 C 0.36025(6) 0.5935(2) 0.54467(4) 0.0177(2) Uani 1 1 d . . .
C2 C 0.32234(7) 0.8413(3) 0.43174(4) 0.0210(2) Uani 1 1 d . . .
H2 H 0.3102 0.9204 0.3927 0.025 Uiso 1 1 calc R . .
C3 C 0.25120(6) 0.6639(3) 0.45275(4) 0.0196(2) Uani 1 1 d . . .
C4 C 0.26969(6) 0.5406(2) 0.51009(4) 0.0181(2) Uani 1 1 d . . .
C5 C 0.16469(7) 0.6184(3) 0.41842(4) 0.0230(2) Uani 1 1 d . . .
H5 H 0.1520 0.6989 0.3795 0.028 Uiso 1 1 calc R . .
C6 C 0.09810(7) 0.4569(3) 0.44115(5) 0.0253(2) Uani 1 1 d . . .
H6 H 0.0395 0.4287 0.4179 0.030 Uiso 1 1 calc R . .
C7 C 0.11681(7) 0.3347(3) 0.49832(5) 0.0243(2) Uani 1 1 d . . .
H7 H 0.0706 0.2245 0.5137 0.029 Uiso 1 1 calc R . .
C8 C 0.20196(7) 0.3728(3) 0.53260(4) 0.0210(2) Uani 1 1 d . . .
H8 H 0.2145 0.2858 0.5711 0.025 Uiso 1 1 calc R . .
N3 N 0.38339(5) 0.4711(2) 0.59743(3) 0.01956(19) Uani 1 1 d . . .
N4 N 0.47273(5) 0.5603(2) 0.62057(3) 0.0204(2) Uani 1 1 d . . .
C9 C 0.50749(6) 0.4095(3) 0.66842(4) 0.0196(2) Uani 1 1 d . . .
H9 H 0.4733 0.2528 0.6863 0.024 Uiso 1 1 calc R . .
C10 C 0.60032(6) 0.4869(3) 0.69410(4) 0.0199(2) Uani 1 1 d . . .
H10 H 0.6309 0.6454 0.6742 0.024 Uiso 1 1 calc R . .
C11 C 0.64688(6) 0.3540(3) 0.74365(4) 0.0200(2) Uani 1 1 d . . .
H11 H 0.6156 0.2017 0.7643 0.024 Uiso 1 1 calc R . .
C12 C 0.74224(6) 0.4237(3) 0.76879(4) 0.0187(2) Uani 1 1 d . . .
C13 C 0.77685(7) 0.3263(3) 0.82618(4) 0.0215(2) Uani 1 1 d . . .
H13 H 0.7385 0.2187 0.8483 0.026 Uiso 1 1 calc R . .
C14 C 0.86694(7) 0.3856(3) 0.85108(4) 0.0246(2) Uani 1 1 d . . .
H14 H 0.8895 0.3201 0.8902 0.030 Uiso 1 1 calc R . .
C15 C 0.92425(7) 0.5397(3) 0.81923(5) 0.0252(2) Uani 1 1 d . . .
H15 H 0.9858 0.5787 0.8364 0.030 Uiso 1 1 calc R . .
C16 C 0.89077(7) 0.6365(3) 0.76197(5) 0.0252(2) Uani 1 1 d . . .
H16 H 0.9296 0.7416 0.7399 0.030 Uiso 1 1 calc R . .
C17 C 0.80085(7) 0.5801(3) 0.73713(4) 0.0222(2) Uani 1 1 d . . .
H17 H 0.7786 0.6483 0.6981 0.027 Uiso 1 1 calc R . .


_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
N1 N2 1.3578(11) . ?
N1 C1 1.3724(12) . ?
N1 H1N 0.9311 . ?
N2 C2 1.2936(13) . ?
C1 N3 1.3092(13) . ?
C1 C4 1.4610(13) . ?
C2 C3 1.4449(14) . ?
C2 H2 0.9500 . ?
C3 C5 1.4047(13) . ?
C3 C4 1.4050(14) . ?
C4 C8 1.4034(14) . ?
C5 C6 1.3808(15) . ?
C5 H5 0.9500 . ?
C6 C7 1.3998(15) . ?
C6 H6 0.9500 . ?
C7 C8 1.3840(14) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
N3 N4 1.3960(11) . ?
N4 C9 1.2855(13) . ?
C9 C10 1.4448(13) . ?
C9 H9 0.9500 . ?
C10 C11 1.3397(14) . ?
C10 H10 0.9500 . ?
C11 C12 1.4704(13) . ?
C11 H11 0.9500 . ?
C12 C13 1.3983(13) . ?
C12 C17 1.4032(14) . ?
C13 C14 1.3903(14) . ?
C13 H13 0.9500 . ?
C14 C15 1.3880(15) . ?
C14 H14 0.9500 . ?
C15 C16 1.3918(15) . ?
C15 H15 0.9500 . ?
C16 C17 1.3861(14) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?

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 N1 C1 126.83(8) . . ?
N2 N1 H1N 114.4 . . ?
C1 N1 H1N 118.8 . . ?
C2 N2 N1 117.30(8) . . ?
N3 C1 N1 122.89(9) . . ?
N3 C1 C4 121.32(9) . . ?
N1 C1 C4 115.78(8) . . ?
N2 C2 C3 123.81(9) . . ?
N2 C2 H2 118.1 . . ?
C3 C2 H2 118.1 . . ?
C5 C3 C4 119.51(9) . . ?
C5 C3 C2 122.37(9) . . ?
C4 C3 C2 118.10(9) . . ?
C8 C4 C3 119.94(9) . . ?
C8 C4 C1 121.95(9) . . ?
C3 C4 C1 118.11(9) . . ?
C6 C5 C3 120.16(9) . . ?
C6 C5 H5 119.9 . . ?
C3 C5 H5 119.9 . . ?
C5 C6 C7 120.12(9) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 H6 119.9 . . ?
C8 C7 C6 120.62(9) . . ?
C8 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
C7 C8 C4 119.63(9) . . ?
C7 C8 H8 120.2 . . ?
C4 C8 H8 120.2 . . ?
C1 N3 N4 109.51(8) . . ?
C9 N4 N3 114.97(8) . . ?
N4 C9 C10 117.64(9) . . ?
N4 C9 H9 121.2 . . ?
C10 C9 H9 121.2 . . ?
C11 C10 C9 125.53(9) . . ?
C11 C10 H10 117.2 . . ?
C9 C10 H10 117.2 . . ?
C10 C11 C12 125.55(9) . . ?
C10 C11 H11 117.2 . . ?
C12 C11 H11 117.2 . . ?
C13 C12 C17 118.28(9) . . ?
C13 C12 C11 119.12(9) . . ?
C17 C12 C11 122.59(9) . . ?
C14 C13 C12 120.57(9) . . ?
C14 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
C15 C14 C13 120.57(9) . . ?
C15 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C14 C15 C16 119.46(9) . . ?
C14 C15 H15 120.3 . . ?
C16 C15 H15 120.3 . . ?
C17 C16 C15 120.14(9) . . ?
C17 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
C16 C17 C12 120.98(9) . . ?
C16 C17 H17 119.5 . . ?
C12 C17 H17 119.5 . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        67.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.213
_refine_diff_density_min         -0.229
_refine_diff_density_rms         0.039

####################################################################### 
# 
# 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_con76
_database_code_depnum_ccdc_archive 'CCDC 1062219'
_audit_update_record             
;
2015-04-28 deposited with the CCDC.
2015-09-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL
_chemical_name_systematic        
'2-(2-nitrobenzylidene)-1-(phthalazin-1(2H)-ylidene)hydrazinium chloride hemihydrate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C15 H12 N5 O2 +), 2(Cl -), H2 O'
_chemical_formula_sum            'C30 H26 Cl2 N10 O5'
_chemical_formula_weight         677.51

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 '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/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

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

_cell_length_a                   15.7972(7)
_cell_length_b                   9.2961(4)
_cell_length_c                   21.2681(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 106.516(2)
_cell_angle_gamma                90.00
_cell_volume                     2994.4(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100.0(1)
_cell_measurement_reflns_used    3820
_cell_measurement_theta_min      2
_cell_measurement_theta_max      50

_exptl_crystal_description       prism
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.503
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1400
_exptl_absorpt_coefficient_mu    2.464
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2003)'
_exptl_absorpt_correction_T_min  0.662
_exptl_absorpt_correction_T_max  0.777
_exptl_special_details           ?

_diffrn_ambient_temperature      100.0(1)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         '30W microsource with MonoCap capillary'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEXII CCD area-detector'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 12.8
_diffrn_standards_number         19
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  17.67
_diffrn_standards_decay_%        0.00
_diffrn_reflns_number            33422
_diffrn_reflns_av_R_equivalents  0.0233
_diffrn_reflns_av_sigmaI/netI    0.0167
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.92
_diffrn_reflns_theta_max         73.10
_reflns_number_total             5974
_reflns_number_gt                5803
_reflns_threshold_expression     >2sigma(I)

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

_computing_data_collection       'APEX2 (Bruker, 2010)'
_computing_cell_refinement       'SAINT-Plus (Bruker, 2009)'
_computing_data_reduction        'SAINT-Plus (Bruker, 2009)'
_computing_structure_solution    'SHELXS (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2008)'
_computing_molecular_graphics    
;XP in SHELXTL/PC (Sheldrick, 2008)
 ORTEP-3 W v. 1.062 (Farrugia 2012)
;
_computing_publication_material  
;SHELXL (Sheldrick, 2008) and
 PLATON (Spek, 2009)
;

_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     
'w=1/[σ²(Fo²)+(0.0691P)²+2.7032P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5974
_refine_ls_number_parameters     443
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0459
_refine_ls_R_factor_gt           0.0452
_refine_ls_wR_factor_ref         0.1271
_refine_ls_wR_factor_gt          0.1265
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_refine_ls_shift/su_max          0.001
_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
N1 N 0.55716(10) 0.73801(17) -0.04098(8) 0.0240(3) Uani 1 1 d . . .
H1N H 0.5996 0.8073 -0.0203 0.029 Uiso 1 1 d R . .
N2 N 0.57785(11) 0.66628(19) -0.09095(9) 0.0308(4) Uani 1 1 d . . .
C1 C 0.48546(11) 0.71585(19) -0.02106(9) 0.0214(4) Uani 1 1 d . . .
C2 C 0.52264(13) 0.5698(2) -0.12093(11) 0.0318(4) Uani 1 1 d . . .
H2 H 0.5362 0.5184 -0.1554 0.038 Uiso 1 1 calc R . .
C3 C 0.44191(12) 0.5342(2) -0.10602(9) 0.0248(4) Uani 1 1 d . . .
C4 C 0.42250(11) 0.60796(19) -0.05408(9) 0.0218(4) Uani 1 1 d . . .
C5 C 0.38451(13) 0.4273(2) -0.14068(10) 0.0278(4) Uani 1 1 d . . .
H5 H 0.3971 0.3787 -0.1763 0.033 Uiso 1 1 calc R . .
C6 C 0.30975(13) 0.3937(2) -0.12252(10) 0.0273(4) Uani 1 1 d . . .
H6 H 0.2705 0.3216 -0.1458 0.033 Uiso 1 1 calc R . .
C7 C 0.29154(12) 0.4651(2) -0.07011(10) 0.0266(4) Uani 1 1 d . . .
H7 H 0.2403 0.4394 -0.0577 0.032 Uiso 1 1 calc R . .
C8 C 0.34624(12) 0.5722(2) -0.03585(9) 0.0242(4) Uani 1 1 d . . .
H8 H 0.3326 0.6208 -0.0007 0.029 Uiso 1 1 calc R . .
N3 N 0.47473(10) 0.79189(17) 0.02938(8) 0.0237(3) Uani 1 1 d . . .
H3N H 0.4261 0.7851 0.0409 0.028 Uiso 1 1 d R . .
N4 N 0.54109(10) 0.88593(16) 0.06033(8) 0.0232(3) Uani 1 1 d . . .
C9 C 0.53092(12) 0.9483(2) 0.11100(10) 0.0274(4) Uani 1 1 d . . .
H9 H 0.4798 0.9319 0.1251 0.033 Uiso 1 1 calc R . .
C10 C 0.60121(12) 1.0471(2) 0.14716(9) 0.0238(4) Uani 1 1 d . . .
C11 C 0.59582(13) 1.1364(2) 0.19906(9) 0.0269(4) Uani 1 1 d . A .
C12 C 0.66334(14) 1.2290(2) 0.23091(10) 0.0319(4) Uani 1 1 d . . .
H12 H 0.6571 1.2890 0.2655 0.038 Uiso 1 1 calc R . .
C13 C 0.73991(14) 1.2325(2) 0.21147(10) 0.0327(4) Uani 1 1 d . . .
H13 H 0.7866 1.2957 0.2326 0.039 Uiso 1 1 calc R . .
C14 C 0.74846(13) 1.1441(2) 0.16148(10) 0.0296(4) Uani 1 1 d . . .
H14 H 0.8016 1.1452 0.1489 0.035 Uiso 1 1 calc R . .
C15 C 0.67990(12) 1.0537(2) 0.12953(10) 0.0268(4) Uani 1 1 d . . .
H15 H 0.6866 0.9948 0.0948 0.032 Uiso 1 1 calc R . .
N5 N 0.51724(12) 1.1371(2) 0.22347(8) 0.0357(4) Uani 1 1 d . . .
O1 O 0.4723(3) 1.0329(5) 0.2193(2) 0.0536(12) Uani 0.732(11) 1 d P A 1
O2 O 0.5028(2) 1.2472(7) 0.2520(2) 0.0562(13) Uani 0.732(11) 1 d P A 1
O1' O 0.4469(5) 1.0853(10) 0.1819(6) 0.042(3) Uani 0.268(11) 1 d P A 2
O2' O 0.5216(7) 1.1785(16) 0.2750(5) 0.053(3) Uani 0.268(11) 1 d P A 2
C21 C 1.09449(11) 0.6014(2) 0.10176(8) 0.0208(4) Uani 1 1 d . . .
N21 N 1.17653(10) 0.60320(17) 0.09587(8) 0.0232(3) Uani 1 1 d . . .
H21N H 1.2076 0.6911 0.1043 0.028 Uiso 1 1 d R . .
N22 N 1.21728(11) 0.49315(18) 0.07301(8) 0.0267(3) Uani 1 1 d . . .
C22 C 1.17239(13) 0.3764(2) 0.05653(9) 0.0259(4) Uani 1 1 d . . .
H22 H 1.1998 0.2981 0.0413 0.031 Uiso 1 1 calc R . .
C23 C 1.08333(12) 0.3574(2) 0.05987(9) 0.0232(4) Uani 1 1 d . . .
C24 C 1.04239(12) 0.47235(19) 0.08302(8) 0.0214(4) Uani 1 1 d . . .
C25 C 1.03691(13) 0.2288(2) 0.04050(9) 0.0272(4) Uani 1 1 d . . .
H25 H 1.0643 0.1509 0.0249 0.033 Uiso 1 1 calc R . .
C26 C 0.95144(14) 0.2153(2) 0.04410(10) 0.0291(4) Uani 1 1 d . . .
H26 H 0.9201 0.1279 0.0313 0.035 Uiso 1 1 calc R . .
C27 C 0.91088(13) 0.3304(2) 0.06670(10) 0.0276(4) Uani 1 1 d . . .
H27 H 0.8517 0.3205 0.0685 0.033 Uiso 1 1 calc R . .
C28 C 0.95523(12) 0.4578(2) 0.08645(9) 0.0236(4) Uani 1 1 d . . .
H28 H 0.9272 0.5348 0.1022 0.028 Uiso 1 1 calc R . .
N23 N 1.06360(10) 0.71821(16) 0.12452(7) 0.0217(3) Uani 1 1 d . . .
H23N H 1.0003 0.7289 0.1205 0.026 Uiso 1 1 d R . .
N24 N 1.11980(10) 0.83448(16) 0.14311(7) 0.0216(3) Uani 1 1 d . . .
C29 C 1.08599(11) 0.9416(2) 0.16540(9) 0.0217(4) Uani 1 1 d . . .
H29 H 1.0269 0.9369 0.1678 0.026 Uiso 1 1 calc R . .
C30 C 1.13903(11) 1.07161(19) 0.18721(8) 0.0211(4) Uani 1 1 d . . .
C31 C 1.10828(12) 1.1856(2) 0.21804(9) 0.0221(4) Uani 1 1 d . . .
C32 C 1.15251(13) 1.3145(2) 0.23384(9) 0.0253(4) Uani 1 1 d . . .
H32 H 1.1283 1.3904 0.2531 0.030 Uiso 1 1 calc R . .
C33 C 1.23323(13) 1.3305(2) 0.22085(9) 0.0267(4) Uani 1 1 d . . .
H33 H 1.2655 1.4176 0.2321 0.032 Uiso 1 1 calc R . .
C34 C 1.26680(12) 1.2195(2) 0.19144(9) 0.0264(4) Uani 1 1 d . . .
H34 H 1.3222 1.2310 0.1828 0.032 Uiso 1 1 calc R . .
C35 C 1.22049(12) 1.0919(2) 0.17446(9) 0.0238(4) Uani 1 1 d . . .
H35 H 1.2442 1.0175 0.1540 0.029 Uiso 1 1 calc R . .
N25 N 1.02540(11) 1.16824(17) 0.23627(8) 0.0258(3) Uani 1 1 d . . .
O21 O 1.01703(11) 1.05923(16) 0.26624(8) 0.0384(4) Uani 1 1 d . . .
O22 O 0.97206(10) 1.26542(18) 0.22291(8) 0.0386(4) Uani 1 1 d . . .
Cl1 Cl 0.68287(3) 1.17935(5) -0.08824(3) 0.03707(15) Uani 1 1 d . . .
Cl21 Cl 0.87225(3) 0.82595(5) 0.10521(2) 0.02877(13) Uani 1 1 d . . .
O99 O 0.70711(9) 0.89178(17) -0.00995(8) 0.0355(3) Uani 1 1 d . . .
H99O H 0.7040 0.9796 -0.0295 0.053 Uiso 1 1 d R . .
H99P H 0.7571 0.8818 0.0265 0.053 Uiso 1 1 d R . .


_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
N1 C1 1.333(2) . ?
N1 N2 1.370(2) . ?
N1 H1N 0.9438 . ?
N2 C2 1.287(3) . ?
C1 N3 1.335(2) . ?
C1 C4 1.446(2) . ?
C2 C3 1.438(3) . ?
C2 H2 0.9500 . ?
C3 C5 1.404(3) . ?
C3 C4 1.406(3) . ?
C4 C8 1.406(2) . ?
C5 C6 1.379(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.396(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.383(3) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
N3 N4 1.380(2) . ?
N3 H3N 0.8727 . ?
N4 C9 1.274(3) . ?
C9 C10 1.477(3) . ?
C9 H9 0.9500 . ?
C10 C15 1.398(3) . ?
C10 C11 1.403(3) . ?
C11 C12 1.388(3) . ?
C11 N5 1.475(3) . ?
C12 C13 1.386(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.380(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.386(3) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
N5 O2' 1.145(9) . ?
N5 O1 1.190(3) . ?
N5 O2 1.243(5) . ?
N5 O1' 1.300(9) . ?
C21 N23 1.337(2) . ?
C21 N21 1.337(2) . ?
C21 C24 1.445(3) . ?
N21 N22 1.370(2) . ?
N21 H21N 0.9437 . ?
N22 C22 1.289(3) . ?
C22 C23 1.439(3) . ?
C22 H22 0.9500 . ?
C23 C25 1.402(3) . ?
C23 C24 1.408(3) . ?
C24 C28 1.406(2) . ?
C25 C26 1.380(3) . ?
C25 H25 0.9500 . ?
C26 C27 1.400(3) . ?
C26 H26 0.9500 . ?
C27 C28 1.380(3) . ?
C27 H27 0.9500 . ?
C28 H28 0.9500 . ?
N23 N24 1.383(2) . ?
N23 H23N 0.9848 . ?
N24 C29 1.283(2) . ?
C29 C30 1.468(2) . ?
C29 H29 0.9500 . ?
C30 C35 1.401(2) . ?
C30 C31 1.404(3) . ?
C31 C32 1.380(3) . ?
C31 N25 1.476(2) . ?
C32 C33 1.387(3) . ?
C32 H32 0.9500 . ?
C33 C34 1.388(3) . ?
C33 H33 0.9500 . ?
C34 C35 1.386(3) . ?
C34 H34 0.9500 . ?
C35 H35 0.9500 . ?
N25 O22 1.213(2) . ?
N25 O21 1.224(2) . ?
O99 H99O 0.9111 . ?
O99 H99P 0.9412 . ?

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
C1 N1 N2 125.64(16) . . ?
C1 N1 H1N 120.8 . . ?
N2 N1 H1N 113.5 . . ?
C2 N2 N1 116.48(16) . . ?
N1 C1 N3 119.14(16) . . ?
N1 C1 C4 118.82(16) . . ?
N3 C1 C4 122.04(16) . . ?
N2 C2 C3 124.77(19) . . ?
N2 C2 H2 117.6 . . ?
C3 C2 H2 117.6 . . ?
C5 C3 C4 120.33(17) . . ?
C5 C3 C2 121.88(18) . . ?
C4 C3 C2 117.78(17) . . ?
C3 C4 C8 119.77(17) . . ?
C3 C4 C1 116.51(16) . . ?
C8 C4 C1 123.69(17) . . ?
C6 C5 C3 119.35(18) . . ?
C6 C5 H5 120.3 . . ?
C3 C5 H5 120.3 . . ?
C5 C6 C7 120.21(18) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 H6 119.9 . . ?
C8 C7 C6 121.58(17) . . ?
C8 C7 H7 119.2 . . ?
C6 C7 H7 119.2 . . ?
C7 C8 C4 118.74(17) . . ?
C7 C8 H8 120.6 . . ?
C4 C8 H8 120.6 . . ?
C1 N3 N4 117.77(15) . . ?
C1 N3 H3N 120.7 . . ?
N4 N3 H3N 121.5 . . ?
C9 N4 N3 115.52(15) . . ?
N4 C9 C10 117.82(16) . . ?
N4 C9 H9 121.1 . . ?
C10 C9 H9 121.1 . . ?
C15 C10 C11 116.28(17) . . ?
C15 C10 C9 118.79(17) . . ?
C11 C10 C9 124.93(17) . . ?
C12 C11 C10 122.73(18) . . ?
C12 C11 N5 115.59(18) . . ?
C10 C11 N5 121.68(17) . . ?
C13 C12 C11 118.93(19) . . ?
C13 C12 H12 120.5 . . ?
C11 C12 H12 120.5 . . ?
C14 C13 C12 120.07(19) . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C13 C14 C15 120.28(19) . . ?
C13 C14 H14 119.9 . . ?
C15 C14 H14 119.9 . . ?
C14 C15 C10 121.69(18) . . ?
C14 C15 H15 119.2 . . ?
C10 C15 H15 119.2 . . ?
O1 N5 O2 121.1(3) . . ?
O2' N5 O1' 125.6(7) . . ?
O2' N5 C11 120.7(5) . . ?
O1 N5 C11 121.0(2) . . ?
O2 N5 C11 117.8(3) . . ?
O1' N5 C11 113.6(4) . . ?
N23 C21 N21 119.15(16) . . ?
N23 C21 C24 122.44(15) . . ?
N21 C21 C24 118.42(16) . . ?
C21 N21 N22 126.14(16) . . ?
C21 N21 H21N 117.4 . . ?
N22 N21 H21N 116.2 . . ?
C22 N22 N21 116.59(15) . . ?
N22 C22 C23 124.01(17) . . ?
N22 C22 H22 118.0 . . ?
C23 C22 H22 118.0 . . ?
C25 C23 C24 119.73(17) . . ?
C25 C23 C22 121.80(17) . . ?
C24 C23 C22 118.47(17) . . ?
C28 C24 C23 119.95(17) . . ?
C28 C24 C21 123.69(16) . . ?
C23 C24 C21 116.36(16) . . ?
C26 C25 C23 119.98(18) . . ?
C26 C25 H25 120.0 . . ?
C23 C25 H25 120.0 . . ?
C25 C26 C27 120.00(18) . . ?
C25 C26 H26 120.0 . . ?
C27 C26 H26 120.0 . . ?
C28 C27 C26 121.23(18) . . ?
C28 C27 H27 119.4 . . ?
C26 C27 H27 119.4 . . ?
C27 C28 C24 119.12(18) . . ?
C27 C28 H28 120.4 . . ?
C24 C28 H28 120.4 . . ?
C21 N23 N24 117.88(14) . . ?
C21 N23 H23N 121.2 . . ?
N24 N23 H23N 120.0 . . ?
C29 N24 N23 114.28(15) . . ?
N24 C29 C30 119.69(16) . . ?
N24 C29 H29 120.2 . . ?
C30 C29 H29 120.2 . . ?
C35 C30 C31 116.58(16) . . ?
C35 C30 C29 121.52(16) . . ?
C31 C30 C29 121.78(16) . . ?
C32 C31 C30 123.44(17) . . ?
C32 C31 N25 117.17(16) . . ?
C30 C31 N25 119.38(16) . . ?
C31 C32 C33 118.38(17) . . ?
C31 C32 H32 120.8 . . ?
C33 C32 H32 120.8 . . ?
C32 C33 C34 120.02(17) . . ?
C32 C33 H33 120.0 . . ?
C34 C33 H33 120.0 . . ?
C35 C34 C33 120.84(17) . . ?
C35 C34 H34 119.6 . . ?
C33 C34 H34 119.6 . . ?
C34 C35 C30 120.70(17) . . ?
C34 C35 H35 119.6 . . ?
C30 C35 H35 119.6 . . ?
O22 N25 O21 124.60(17) . . ?
O22 N25 C31 117.78(16) . . ?
O21 N25 C31 117.55(16) . . ?
H99O O99 H99P 112.8 . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        67.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.836
_refine_diff_density_min         -0.439
_refine_diff_density_rms         0.064


####################################################################### 
# 
# 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_con76a
_database_code_depnum_ccdc_archive 'CCDC 1062220'
_audit_update_record             
;
2015-04-28 deposited with the CCDC.
2015-09-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL
_chemical_name_systematic        
; 
3-(2-nitrophenyl)[1,2,4]triazolo[3,4-a]phthalazine
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H9 N5 O2'
_chemical_formula_sum            'C15 H9 N5 O2'
_chemical_formula_weight         291.27

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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                   7.6745(5)
_cell_length_b                   12.8403(11)
_cell_length_c                   12.6474(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.174(6)
_cell_angle_gamma                90.00
_cell_volume                     1246.05(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    100.0(1)
_cell_measurement_reflns_used    894
_cell_measurement_theta_min      2
_cell_measurement_theta_max      50

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.553
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             600
_exptl_absorpt_coefficient_mu    0.908
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2003)'
_exptl_absorpt_correction_T_min  0.860
_exptl_absorpt_correction_T_max  0.879
_exptl_special_details           ?

_diffrn_ambient_temperature      100.0(1)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         '30W microsource with MonoCap capillary'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEXII CCD area-detector'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 12.8
_diffrn_standards_number         4
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  19.33
_diffrn_standards_decay_%        0.00
_diffrn_reflns_number            14080
_diffrn_reflns_av_R_equivalents  0.0209
_diffrn_reflns_av_sigmaI/netI    0.0132
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         4.91
_diffrn_reflns_theta_max         72.32
_reflns_number_total             2464
_reflns_number_gt                2406
_reflns_threshold_expression     >2sigma(I)

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

_computing_data_collection       'APEX2 (Bruker, 2010)'
_computing_cell_refinement       'SAINT-Plus (Bruker, 2009)'
_computing_data_reduction        'SAINT-Plus (Bruker, 2009)'
_computing_structure_solution    'SHELXS (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2008)'
_computing_molecular_graphics    
;XP in SHELXTL/PC (Sheldrick, 2008)
 ORTEP-3 W v. 1.062 (Farrugia 2012)
;
_computing_publication_material  
;SHELXL (Sheldrick, 2008) and
 PLATON (Spek, 2009)
;

_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     
'w=1/[σ²(Fo²)+(0.0402P)²+0.5805P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0069(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2464
_refine_ls_number_parameters     200
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0309
_refine_ls_R_factor_gt           0.0304
_refine_ls_wR_factor_ref         0.0808
_refine_ls_wR_factor_gt          0.0803
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_restrained_S_all      1.064
_refine_ls_shift/su_max          0.001
_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 0.37705(13) 0.62373(8) 0.41226(8) 0.0128(2) Uani 1 1 d . . .
N1 N 0.35436(11) 0.59115(7) 0.30943(7) 0.0124(2) Uani 1 1 d . . .
N2 N 0.27520(11) 0.50160(7) 0.27227(7) 0.0142(2) Uani 1 1 d . . .
C2 C 0.21446(14) 0.44357(8) 0.34673(9) 0.0145(2) Uani 1 1 d . . .
H2 H 0.1594 0.3803 0.3260 0.017 Uiso 1 1 calc R . .
C3 C 0.22318(14) 0.46668(8) 0.45869(8) 0.0136(2) Uani 1 1 d . . .
C4 C 0.30520(13) 0.55911(8) 0.49395(8) 0.0131(2) Uani 1 1 d . . .
C5 C 0.14902(14) 0.39914(8) 0.53246(9) 0.0153(2) Uani 1 1 d . . .
H5 H 0.0940 0.3367 0.5093 0.018 Uiso 1 1 calc R . .
C6 C 0.15605(14) 0.42354(9) 0.63875(9) 0.0172(2) Uani 1 1 d . . .
H6 H 0.1068 0.3775 0.6887 0.021 Uiso 1 1 calc R . .
C7 C 0.23557(15) 0.51594(9) 0.67303(9) 0.0185(2) Uani 1 1 d . . .
H7 H 0.2381 0.5325 0.7463 0.022 Uiso 1 1 calc R . .
C8 C 0.31088(14) 0.58384(9) 0.60186(9) 0.0163(2) Uani 1 1 d . . .
H8 H 0.3654 0.6461 0.6259 0.020 Uiso 1 1 calc R . .
N3 N 0.46415(12) 0.71211(7) 0.41486(7) 0.0150(2) Uani 1 1 d . . .
N4 N 0.49877(12) 0.73819(7) 0.31027(7) 0.0150(2) Uani 1 1 d . . .
C9 C 0.43176(13) 0.66530(8) 0.24896(8) 0.0131(2) Uani 1 1 d . . .
C10 C 0.43994(14) 0.65735(8) 0.13289(8) 0.0130(2) Uani 1 1 d . . .
C11 C 0.29225(14) 0.64203(8) 0.06786(8) 0.0132(2) Uani 1 1 d . . .
C12 C 0.30127(14) 0.62636(8) -0.04004(9) 0.0155(2) Uani 1 1 d . . .
H12 H 0.1986 0.6155 -0.0818 0.019 Uiso 1 1 calc R . .
C13 C 0.46480(15) 0.62695(9) -0.08592(9) 0.0171(2) Uani 1 1 d . . .
H13 H 0.4742 0.6170 -0.1600 0.020 Uiso 1 1 calc R . .
C14 C 0.61412(15) 0.64193(9) -0.02389(9) 0.0174(2) Uani 1 1 d . . .
H14 H 0.7252 0.6419 -0.0557 0.021 Uiso 1 1 calc R . .
C15 C 0.60189(14) 0.65695(8) 0.08474(9) 0.0155(2) Uani 1 1 d . . .
H15 H 0.7048 0.6670 0.1265 0.019 Uiso 1 1 calc R . .
N5 N 0.11751(11) 0.64696(7) 0.11313(7) 0.0143(2) Uani 1 1 d . . .
O1 O 0.09245(10) 0.71315(6) 0.18216(6) 0.0180(2) Uani 1 1 d . . .
O2 O 0.00672(10) 0.58659(7) 0.07961(7) 0.0219(2) Uani 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
C1 N3 1.3171(14) . ?
C1 N1 1.3739(13) . ?
C1 C4 1.4433(15) . ?
N1 C9 1.3648(14) . ?
N1 N2 1.3786(12) . ?
N2 C2 1.2951(14) . ?
C2 C3 1.4470(15) . ?
C2 H2 0.9500 . ?
C3 C5 1.4029(15) . ?
C3 C4 1.4115(15) . ?
C4 C8 1.4011(15) . ?
C5 C6 1.3803(15) . ?
C5 H5 0.9500 . ?
C6 C7 1.3990(17) . ?
C6 H6 0.9500 . ?
C7 C8 1.3878(16) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
N3 N4 1.3954(12) . ?
N4 C9 1.3135(14) . ?
C9 C10 1.4741(15) . ?
C10 C15 1.3952(15) . ?
C10 C11 1.4006(15) . ?
C11 C12 1.3825(15) . ?
C11 N5 1.4703(13) . ?
C12 C13 1.3934(15) . ?
C12 H12 0.9500 . ?
C13 C14 1.3888(16) . ?
C13 H13 0.9500 . ?
C14 C15 1.3924(16) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
N5 O2 1.2201(12) . ?
N5 O1 1.2363(12) . ?

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
N3 C1 N1 109.90(9) . . ?
N3 C1 C4 132.73(10) . . ?
N1 C1 C4 117.37(9) . . ?
C9 N1 C1 105.66(9) . . ?
C9 N1 N2 125.78(9) . . ?
C1 N1 N2 128.54(9) . . ?
C2 N2 N1 113.25(9) . . ?
N2 C2 C3 125.70(10) . . ?
N2 C2 H2 117.2 . . ?
C3 C2 H2 117.2 . . ?
C5 C3 C4 119.61(10) . . ?
C5 C3 C2 120.85(10) . . ?
C4 C3 C2 119.54(10) . . ?
C8 C4 C3 120.21(10) . . ?
C8 C4 C1 124.21(10) . . ?
C3 C4 C1 115.58(9) . . ?
C6 C5 C3 119.94(10) . . ?
C6 C5 H5 120.0 . . ?
C3 C5 H5 120.0 . . ?
C5 C6 C7 120.16(10) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 H6 119.9 . . ?
C8 C7 C6 121.10(10) . . ?
C8 C7 H7 119.4 . . ?
C6 C7 H7 119.4 . . ?
C7 C8 C4 118.97(10) . . ?
C7 C8 H8 120.5 . . ?
C4 C8 H8 120.5 . . ?
C1 N3 N4 106.83(9) . . ?
C9 N4 N3 107.99(9) . . ?
N4 C9 N1 109.62(9) . . ?
N4 C9 C10 127.81(9) . . ?
N1 C9 C10 122.52(9) . . ?
C15 C10 C11 117.43(10) . . ?
C15 C10 C9 119.43(9) . . ?
C11 C10 C9 122.96(9) . . ?
C12 C11 C10 122.94(10) . . ?
C12 C11 N5 117.07(9) . . ?
C10 C11 N5 119.93(9) . . ?
C11 C12 C13 118.29(10) . . ?
C11 C12 H12 120.9 . . ?
C13 C12 H12 120.9 . . ?
C14 C13 C12 120.35(10) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C13 C14 C15 120.34(10) . . ?
C13 C14 H14 119.8 . . ?
C15 C14 H14 119.8 . . ?
C14 C15 C10 120.65(10) . . ?
C14 C15 H15 119.7 . . ?
C10 C15 H15 119.7 . . ?
O2 N5 O1 124.38(9) . . ?
O2 N5 C11 118.17(9) . . ?
O1 N5 C11 117.45(9) . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        67.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.303
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.041

####################################################################### 
# 
# 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_con75
_database_code_depnum_ccdc_archive 'CCDC 1062221'
_audit_update_record             
;
2015-04-28 deposited with the CCDC.
2015-09-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL
_chemical_name_systematic        
; 
2-(3-nitrobenzylidene)-1-(phthalazin-1(2H)-ylidene)hydrazinium chloride 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H12 N5 O2 +, Cl -'
_chemical_formula_sum            'C15 H12 Cl N5 O2'
_chemical_formula_weight         329.75

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 '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                   7.9151(8)
_cell_length_b                   14.3022(11)
_cell_length_c                   12.8292(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 105.157(9)
_cell_angle_gamma                90.00
_cell_volume                     1401.8(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100.0(1)
_cell_measurement_reflns_used    588
_cell_measurement_theta_min      2
_cell_measurement_theta_max      50

_exptl_crystal_description       'hexagonal plate'
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.562
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             680
_exptl_absorpt_coefficient_mu    2.588
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2003)'
_exptl_absorpt_correction_T_min  0.663
_exptl_absorpt_correction_T_max  0.851
_exptl_special_details           ?

_diffrn_ambient_temperature      100.0(1)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         '30W microsource with MonoCap capillary'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEXII CCD  area-detector'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 12.8
_diffrn_standards_number         4
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  11.17
_diffrn_standards_decay_%        0.00
_diffrn_reflns_number            15844
_diffrn_reflns_av_R_equivalents  0.0180
_diffrn_reflns_av_sigmaI/netI    0.0122
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         4.72
_diffrn_reflns_theta_max         72.43
_reflns_number_total             2768
_reflns_number_gt                2759
_reflns_threshold_expression     >2sigma(I)

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

_computing_data_collection       'APEX2 (Bruker, 2010)'
_computing_cell_refinement       'SAINT-Plus (Bruker, 2009)'
_computing_data_reduction        'SAINT-Plus (Bruker, 2009)'
_computing_structure_solution    'SHELXS (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2008)'
_computing_molecular_graphics    
;XP in SHELXTL/PC (Sheldrick, 2008)
 ORTEP-3 W v. 1.062 (Farrugia 2012)
;
_computing_publication_material  
;SHELXL (Sheldrick, 2008) and
 PLATON (Spek, 2009)
;

_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     
'w=1/[σ²(Fo²)+(0.0385P)²+0.7827P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0023(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2768
_refine_ls_number_parameters     209
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0255
_refine_ls_R_factor_gt           0.0254
_refine_ls_wR_factor_ref         0.0716
_refine_ls_wR_factor_gt          0.0715
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_refine_ls_shift/su_max          0.001
_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 0.05811(14) 0.05024(8) 0.79996(9) 0.0106(2) Uani 1 1 d . . .
N1 N 0.09512(12) -0.04100(7) 0.80033(8) 0.0123(2) Uani 1 1 d . . .
H1N H 0.1876 -0.0612 0.7817 0.015 Uiso 1 1 d R . .
N2 N 0.00402(13) -0.11174(7) 0.83370(8) 0.0151(2) Uani 1 1 d . . .
C2 C -0.12475(15) -0.08611(8) 0.87197(10) 0.0147(2) Uani 1 1 d . . .
H2 H -0.1917 -0.1337 0.8940 0.018 Uiso 1 1 calc R . .
C3 C -0.17310(14) 0.00905(8) 0.88331(9) 0.0119(2) Uani 1 1 d . . .
C4 C -0.08200(14) 0.08038(8) 0.84543(9) 0.0108(2) Uani 1 1 d . . .
C5 C -0.31053(15) 0.03160(8) 0.92921(9) 0.0142(2) Uani 1 1 d . . .
H5 H -0.3722 -0.0165 0.9547 0.017 Uiso 1 1 calc R . .
C6 C -0.35537(15) 0.12372(9) 0.93703(10) 0.0155(2) Uani 1 1 d . . .
H6 H -0.4467 0.1395 0.9694 0.019 Uiso 1 1 calc R . .
C7 C -0.26657(16) 0.19439(9) 0.89738(10) 0.0162(2) Uani 1 1 d . . .
H7 H -0.3005 0.2577 0.9019 0.019 Uiso 1 1 calc R . .
C8 C -0.13072(15) 0.17410(8) 0.85189(10) 0.0135(2) Uani 1 1 d . . .
H8 H -0.0714 0.2227 0.8255 0.016 Uiso 1 1 calc R . .
N3 N 0.15026(12) 0.11080(7) 0.75761(8) 0.0114(2) Uani 1 1 d . . .
H3N H 0.1317 0.1724 0.7576 0.014 Uiso 1 1 d R . .
N4 N 0.28018(12) 0.07446(7) 0.71606(8) 0.0116(2) Uani 1 1 d . . .
C9 C 0.36812(15) 0.13394(8) 0.67697(9) 0.0119(2) Uani 1 1 d . . .
H9 H 0.3412 0.1987 0.6755 0.014 Uiso 1 1 calc R . .
C10 C 0.51130(14) 0.09943(8) 0.63450(9) 0.0113(2) Uani 1 1 d . . .
C11 C 0.59729(15) 0.16091(8) 0.58120(9) 0.0117(2) Uani 1 1 d . . .
H11 H 0.5632 0.2247 0.5715 0.014 Uiso 1 1 calc R . .
C12 C 0.73373(14) 0.12684(8) 0.54274(9) 0.0122(2) Uani 1 1 d . . .
C13 C 0.78730(15) 0.03437(8) 0.55500(9) 0.0139(2) Uani 1 1 d . . .
H13 H 0.8814 0.0129 0.5281 0.017 Uiso 1 1 calc R . .
C14 C 0.69975(15) -0.02594(8) 0.60755(9) 0.0139(2) Uani 1 1 d . . .
H14 H 0.7339 -0.0897 0.6164 0.017 Uiso 1 1 calc R . .
C15 C 0.56355(15) 0.00537(8) 0.64722(9) 0.0121(2) Uani 1 1 d . . .
H15 H 0.5051 -0.0368 0.6832 0.015 Uiso 1 1 calc R . .
N5 N 0.82587(13) 0.19068(7) 0.48658(8) 0.0144(2) Uani 1 1 d . . .
O1 O 0.76975(11) 0.27075(6) 0.46797(7) 0.01678(19) Uani 1 1 d . . .
O2 O 0.95489(12) 0.16084(7) 0.46111(8) 0.0251(2) Uani 1 1 d . . .
Cl1 Cl 0.08899(3) 0.324629(18) 0.70962(2) 0.01432(10) Uani 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
C1 N3 1.3360(15) . ?
C1 N1 1.3371(15) . ?
C1 C4 1.4471(15) . ?
N1 N2 1.3742(13) . ?
N1 H1N 0.8765 . ?
N2 C2 1.2946(15) . ?
C2 C3 1.4315(16) . ?
C2 H2 0.9500 . ?
C3 C5 1.4033(16) . ?
C3 C4 1.4071(16) . ?
C4 C8 1.4032(16) . ?
C5 C6 1.3749(17) . ?
C5 H5 0.9500 . ?
C6 C7 1.4005(17) . ?
C6 H6 0.9500 . ?
C7 C8 1.3818(16) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
N3 N4 1.3778(13) . ?
N3 H3N 0.8928 . ?
N4 C9 1.2815(15) . ?
C9 C10 1.4655(15) . ?
C9 H9 0.9500 . ?
C10 C11 1.3955(16) . ?
C10 C15 1.4043(16) . ?
C11 C12 1.3878(16) . ?
C11 H11 0.9500 . ?
C12 C13 1.3852(17) . ?
C12 N5 1.4695(14) . ?
C13 C14 1.3867(17) . ?
C13 H13 0.9500 . ?
C14 C15 1.3815(16) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
N5 O2 1.2273(14) . ?
N5 O1 1.2289(14) . ?

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
N3 C1 N1 119.46(10) . . ?
N3 C1 C4 121.88(10) . . ?
N1 C1 C4 118.66(10) . . ?
C1 N1 N2 125.97(10) . . ?
C1 N1 H1N 121.2 . . ?
N2 N1 H1N 112.7 . . ?
C2 N2 N1 116.04(10) . . ?
N2 C2 C3 124.45(11) . . ?
N2 C2 H2 117.8 . . ?
C3 C2 H2 117.8 . . ?
C5 C3 C4 120.12(11) . . ?
C5 C3 C2 121.22(11) . . ?
C4 C3 C2 118.65(10) . . ?
C8 C4 C3 119.90(10) . . ?
C8 C4 C1 124.04(10) . . ?
C3 C4 C1 116.05(10) . . ?
C6 C5 C3 119.61(11) . . ?
C6 C5 H5 120.2 . . ?
C3 C5 H5 120.2 . . ?
C5 C6 C7 120.09(11) . . ?
C5 C6 H6 120.0 . . ?
C7 C6 H6 120.0 . . ?
C8 C7 C6 121.45(11) . . ?
C8 C7 H7 119.3 . . ?
C6 C7 H7 119.3 . . ?
C7 C8 C4 118.80(11) . . ?
C7 C8 H8 120.6 . . ?
C4 C8 H8 120.6 . . ?
C1 N3 N4 117.05(9) . . ?
C1 N3 H3N 122.2 . . ?
N4 N3 H3N 120.8 . . ?
C9 N4 N3 115.96(10) . . ?
N4 C9 C10 118.29(10) . . ?
N4 C9 H9 120.9 . . ?
C10 C9 H9 120.9 . . ?
C11 C10 C15 119.60(10) . . ?
C11 C10 C9 119.58(10) . . ?
C15 C10 C9 120.82(10) . . ?
C12 C11 C10 118.52(11) . . ?
C12 C11 H11 120.7 . . ?
C10 C11 H11 120.7 . . ?
C13 C12 C11 122.58(11) . . ?
C13 C12 N5 118.20(10) . . ?
C11 C12 N5 119.22(10) . . ?
C12 C13 C14 118.16(11) . . ?
C12 C13 H13 120.9 . . ?
C14 C13 H13 120.9 . . ?
C15 C14 C13 120.98(11) . . ?
C15 C14 H14 119.5 . . ?
C13 C14 H14 119.5 . . ?
C14 C15 C10 120.14(11) . . ?
C14 C15 H15 119.9 . . ?
C10 C15 H15 119.9 . . ?
O2 N5 O1 123.78(10) . . ?
O2 N5 C12 117.94(10) . . ?
O1 N5 C12 118.28(9) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        67.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.312
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.045

####################################################################### 
# 
# 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_con75fr2
_database_code_depnum_ccdc_archive 'CCDC 1062222'
_audit_update_record             
;
2015-04-28 deposited with the CCDC.
2015-09-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL
_chemical_name_systematic        
; 
2-(3-nitrobenzylidene)-1-(phthalazin-1(2H)-ylidene)hydrazine 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H11 N5 O2'
_chemical_formula_sum            'C15 H11 N5 O2'
_chemical_formula_weight         293.29

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

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

_cell_length_a                   14.1361(9)
_cell_length_b                   3.7858(3)
_cell_length_c                   24.2876(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.009(6)
_cell_angle_gamma                90.00
_cell_volume                     1296.61(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    100.0(1)
_cell_measurement_reflns_used    397
_cell_measurement_theta_min      2
_cell_measurement_theta_max      50

_exptl_crystal_description       needle
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.024
_exptl_crystal_size_mid          0.017
_exptl_crystal_size_min          0.013
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.502
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             608
_exptl_absorpt_coefficient_mu    0.873
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2003)'
_exptl_absorpt_correction_T_min  0.975
_exptl_absorpt_correction_T_max  0.996
_exptl_special_details           ?

_diffrn_ambient_temperature      100.0(1)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         '30W microsource with MonoCap capillary'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEXII CCD area-detector'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 12.8
_diffrn_standards_number         4
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  11.17
_diffrn_standards_decay_%        0.00
_diffrn_reflns_number            11199
_diffrn_reflns_av_R_equivalents  0.0251
_diffrn_reflns_av_sigmaI/netI    0.0195
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -3
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         3.13
_diffrn_reflns_theta_max         72.26
_reflns_number_total             2555
_reflns_number_gt                2334
_reflns_threshold_expression     >2sigma(I)

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

_computing_data_collection       'APEX2 (Bruker, 2010)'
_computing_cell_refinement       'SAINT-Plus (Bruker, 2009)'
_computing_data_reduction        'SAINT-Plus (Bruker, 2009)'
_computing_structure_solution    'SHELXS (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2008)'
_computing_molecular_graphics    
;XP in SHELXTL/PC (Sheldrick, 2008)
 ORTEP-3 W v. 1.062 (Farrugia 2012)
;
_computing_publication_material  
;SHELXL (Sheldrick, 2008) and
 PLATON (Spek, 2009)
;

_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     
'w=1/[σ²(Fo²)+(0.0530P)²+0.4228P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2555
_refine_ls_number_parameters     200
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0363
_refine_ls_R_factor_gt           0.0328
_refine_ls_wR_factor_ref         0.0929
_refine_ls_wR_factor_gt          0.0891
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_refine_ls_shift/su_max          0.001
_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 1.10661(8) 0.4183(3) 0.41449(4) 0.0167(2) Uani 1 1 d . . .
N1 N 1.06136(6) 0.2464(3) 0.45468(4) 0.0183(2) Uani 1 1 d . . .
H1N H 1.0011 0.1800 0.4487 0.026(4) Uiso 1 1 d R . .
N2 N 1.09913(7) 0.1587(3) 0.50622(4) 0.0193(2) Uani 1 1 d . . .
C2 C 1.18675(8) 0.2424(3) 0.51844(5) 0.0193(2) Uani 1 1 d . . .
H2 H 1.2135 0.1859 0.5543 0.023 Uiso 1 1 calc R . .
C3 C 1.24656(8) 0.4165(3) 0.48092(4) 0.0176(2) Uani 1 1 d . . .
C4 C 1.20612(8) 0.5045(3) 0.42829(5) 0.0167(2) Uani 1 1 d . . .
C5 C 1.34182(8) 0.4972(3) 0.49530(5) 0.0201(2) Uani 1 1 d . . .
H5 H 1.3693 0.4392 0.5310 0.024 Uiso 1 1 calc R . .
C6 C 1.39565(8) 0.6615(3) 0.45740(5) 0.0212(3) Uani 1 1 d . . .
H6 H 1.4603 0.7157 0.4671 0.025 Uiso 1 1 calc R . .
C7 C 1.35559(8) 0.7484(3) 0.40496(5) 0.0205(3) Uani 1 1 d . . .
H7 H 1.3933 0.8595 0.3791 0.025 Uiso 1 1 calc R . .
C8 C 1.26142(8) 0.6740(3) 0.39040(5) 0.0184(2) Uani 1 1 d . . .
H8 H 1.2342 0.7373 0.3549 0.022 Uiso 1 1 calc R . .
N3 N 1.06751(6) 0.5105(3) 0.36623(4) 0.0187(2) Uani 1 1 d . . .
N4 N 0.97094(6) 0.4353(3) 0.35987(4) 0.0188(2) Uani 1 1 d . . .
C9 C 0.93376(8) 0.5514(3) 0.31363(4) 0.0187(2) Uani 1 1 d . . .
H9 H 0.9740 0.6593 0.2888 0.022 Uiso 1 1 calc R . .
C10 C 0.83232(8) 0.5252(3) 0.29743(5) 0.0179(2) Uani 1 1 d . . .
C11 C 0.76794(8) 0.3747(3) 0.33204(4) 0.0180(2) Uani 1 1 d . . .
H11 H 0.7892 0.2772 0.3668 0.022 Uiso 1 1 calc R . .
C12 C 0.67277(8) 0.3715(3) 0.31446(4) 0.0183(2) Uani 1 1 d . . .
C13 C 0.63740(8) 0.5110(3) 0.26429(5) 0.0193(2) Uani 1 1 d . . .
H13 H 0.5714 0.5065 0.2537 0.023 Uiso 1 1 calc R . .
C14 C 0.70190(8) 0.6574(3) 0.23014(5) 0.0199(2) Uani 1 1 d . . .
H14 H 0.6800 0.7544 0.1955 0.024 Uiso 1 1 calc R . .
C15 C 0.79814(8) 0.6630(3) 0.24623(5) 0.0195(2) Uani 1 1 d . . .
H15 H 0.8414 0.7615 0.2222 0.023 Uiso 1 1 calc R . .
N5 N 0.60442(7) 0.2095(3) 0.35012(4) 0.0207(2) Uani 1 1 d . . .
O1 O 0.63519(6) 0.0494(2) 0.39148(3) 0.0271(2) Uani 1 1 d . . .
O2 O 0.51972(6) 0.2399(3) 0.33639(4) 0.0342(3) Uani 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
C1 N3 1.3080(14) . ?
C1 N1 1.3685(14) . ?
C1 C4 1.4601(15) . ?
N1 N2 1.3670(13) . ?
N1 H1N 0.8904 . ?
N2 C2 1.2927(14) . ?
C2 C3 1.4447(15) . ?
C2 H2 0.9500 . ?
C3 C5 1.4009(16) . ?
C3 C4 1.4034(15) . ?
C4 C8 1.4036(15) . ?
C5 C6 1.3825(16) . ?
C5 H5 0.9500 . ?
C6 C7 1.3967(16) . ?
C6 H6 0.9500 . ?
C7 C8 1.3823(15) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
N3 N4 1.3925(13) . ?
N4 C9 1.2839(15) . ?
C9 C10 1.4636(15) . ?
C9 H9 0.9500 . ?
C10 C11 1.4024(15) . ?
C10 C15 1.4030(15) . ?
C11 C12 1.3829(15) . ?
C11 H11 0.9500 . ?
C12 C13 1.3886(16) . ?
C12 N5 1.4755(14) . ?
C13 C14 1.3901(16) . ?
C13 H13 0.9500 . ?
C14 C15 1.3891(16) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
N5 O2 1.2257(12) . ?
N5 O1 1.2264(13) . ?

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
N3 C1 N1 125.23(10) . . ?
N3 C1 C4 119.08(10) . . ?
N1 C1 C4 115.68(10) . . ?
N2 N1 C1 126.63(9) . . ?
N2 N1 H1N 112.9 . . ?
C1 N1 H1N 120.4 . . ?
C2 N2 N1 117.21(9) . . ?
N2 C2 C3 124.10(10) . . ?
N2 C2 H2 117.9 . . ?
C3 C2 H2 117.9 . . ?
C5 C3 C4 119.90(10) . . ?
C5 C3 C2 122.48(10) . . ?
C4 C3 C2 117.62(10) . . ?
C3 C4 C8 119.72(10) . . ?
C3 C4 C1 118.73(10) . . ?
C8 C4 C1 121.56(10) . . ?
C6 C5 C3 119.76(11) . . ?
C6 C5 H5 120.1 . . ?
C3 C5 H5 120.1 . . ?
C5 C6 C7 120.41(10) . . ?
C5 C6 H6 119.8 . . ?
C7 C6 H6 119.8 . . ?
C8 C7 C6 120.47(10) . . ?
C8 C7 H7 119.8 . . ?
C6 C7 H7 119.8 . . ?
C7 C8 C4 119.74(10) . . ?
C7 C8 H8 120.1 . . ?
C4 C8 H8 120.1 . . ?
C1 N3 N4 113.22(9) . . ?
C9 N4 N3 111.41(9) . . ?
N4 C9 C10 123.05(10) . . ?
N4 C9 H9 118.5 . . ?
C10 C9 H9 118.5 . . ?
C11 C10 C15 118.99(10) . . ?
C11 C10 C9 122.08(10) . . ?
C15 C10 C9 118.90(10) . . ?
C12 C11 C10 118.46(10) . . ?
C12 C11 H11 120.8 . . ?
C10 C11 H11 120.8 . . ?
C11 C12 C13 123.40(10) . . ?
C11 C12 N5 119.02(10) . . ?
C13 C12 N5 117.57(10) . . ?
C12 C13 C14 117.66(10) . . ?
C12 C13 H13 121.2 . . ?
C14 C13 H13 121.2 . . ?
C15 C14 C13 120.57(10) . . ?
C15 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C14 C15 C10 120.90(10) . . ?
C14 C15 H15 119.6 . . ?
C10 C15 H15 119.6 . . ?
O2 N5 O1 123.58(10) . . ?
O2 N5 C12 117.93(9) . . ?
O1 N5 C12 118.48(9) . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        67.00
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.240
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.042

####################################################################### 
# 
# 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_con75bezb
_database_code_depnum_ccdc_archive 'CCDC 1062223'
_audit_update_record             
;
2015-04-28 deposited with the CCDC.
2015-09-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL
_chemical_name_systematic        
; 
3-(3-nitrophenyl)[1,2,4]triazolo[3,4-a]phthalazine
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H9 N5 O2'
_chemical_formula_sum            'C15 H9 N5 O2'
_chemical_formula_weight         291.27

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.6948(8)
_cell_length_b                   7.7883(8)
_cell_length_c                   23.7516(19)
_cell_angle_alpha                85.640(4)
_cell_angle_beta                 84.706(5)
_cell_angle_gamma                61.897(4)
_cell_volume                     1249.4(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    291(1)
_cell_measurement_reflns_used    983
_cell_measurement_theta_min      2
_cell_measurement_theta_max      50

_exptl_crystal_description       needle
_exptl_crystal_colour            'light yellow'
_exptl_crystal_size_max          0.025
_exptl_crystal_size_mid          0.012
_exptl_crystal_size_min          0.012
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.549
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             600
_exptl_absorpt_coefficient_mu    0.905
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2003)'
_exptl_absorpt_correction_T_min  0.982
_exptl_absorpt_correction_T_max  1.000
_exptl_special_details           ?

_diffrn_ambient_temperature      291(1)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         '30W microsource with MonoCap capillary'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEXII CCD area-detector'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 12.8
_diffrn_standards_number         4
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  16.33
_diffrn_standards_decay_%        0.00
_diffrn_reflns_number            8915
_diffrn_reflns_av_R_equivalents  0.0465
_diffrn_reflns_av_sigmaI/netI    0.0590
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         3.74
_diffrn_reflns_theta_max         67.00
_reflns_number_total             4458
_reflns_number_gt                3303
_reflns_threshold_expression     >2sigma(I)

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

_computing_data_collection       'APEX2 (Bruker, 2010)'
_computing_cell_refinement       'SAINT-Plus (Bruker, 2009)'
_computing_data_reduction        'SAINT-Plus (Bruker, 2009)'
_computing_structure_solution    'SHELXS (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2008)'
_computing_molecular_graphics    
;XP in SHELXTL/PC (Sheldrick, 2008)
 ORTEP-3 W v. 1.062 (Farrugia 2012)
;
_computing_publication_material  
;SHELXL (Sheldrick, 2008) and
 PLATON (Spek, 2009)
;

_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     
'w=1/[σ²(Fo²)+(0.1402P)²+0.0114P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4458
_refine_ls_number_parameters     397
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0932
_refine_ls_R_factor_gt           0.0689
_refine_ls_wR_factor_ref         0.2052
_refine_ls_wR_factor_gt          0.1906
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.063
_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
C1 C 0.8386(4) 0.6971(4) 0.43348(12) 0.0468(6) Uani 1 1 d . . .
N1 N 0.7666(3) 0.7696(3) 0.48615(10) 0.0454(5) Uani 1 1 d . . .
N2 N 0.7431(3) 0.9424(3) 0.50487(11) 0.0511(6) Uani 1 1 d . . .
C2 C 0.8031(4) 1.0352(4) 0.46820(13) 0.0513(7) Uani 1 1 d . . .
H2 H 0.7920 1.1521 0.4792 0.062 Uiso 1 1 calc R . .
C3 C 0.8861(4) 0.9779(4) 0.41174(12) 0.0484(6) Uani 1 1 d . . .
C4 C 0.8995(4) 0.8054(4) 0.39298(12) 0.0486(6) Uani 1 1 d . . .
C5 C 0.9475(4) 1.0892(4) 0.37565(14) 0.0566(7) Uani 1 1 d . . .
H5 H 0.9402 1.2031 0.3880 0.068 Uiso 1 1 calc R . .
C6 C 1.0194(5) 1.0309(5) 0.32148(15) 0.0630(8) Uani 1 1 d . . .
H6 H 1.0614 1.1053 0.2972 0.076 Uiso 1 1 calc R . .
C7 C 1.0296(5) 0.8627(5) 0.30294(14) 0.0622(8) Uani 1 1 d . . .
H7 H 1.0768 0.8259 0.2660 0.075 Uiso 1 1 calc R . .
C8 C 0.9717(4) 0.7499(4) 0.33780(13) 0.0558(7) Uani 1 1 d . . .
H8 H 0.9803 0.6362 0.3249 0.067 Uiso 1 1 calc R . .
N3 N 0.8420(4) 0.5285(3) 0.43097(11) 0.0539(6) Uani 1 1 d . . .
N4 N 0.7714(3) 0.4904(3) 0.48314(11) 0.0526(6) Uani 1 1 d . . .
C9 C 0.7248(4) 0.6363(4) 0.51611(12) 0.0475(6) Uani 1 1 d . . .
C10 C 0.6477(4) 0.6424(4) 0.57463(12) 0.0470(6) Uani 1 1 d . . .
C11 C 0.5940(4) 0.5008(4) 0.59402(13) 0.0507(7) Uani 1 1 d . . .
H11 H 0.6074 0.4055 0.5701 0.061 Uiso 1 1 calc R . .
C12 C 0.5207(4) 0.5034(4) 0.64909(13) 0.0531(7) Uani 1 1 d . . .
C13 C 0.4943(4) 0.6433(4) 0.68597(14) 0.0579(7) Uani 1 1 d . . .
H13 H 0.4407 0.6441 0.7227 0.070 Uiso 1 1 calc R . .
C14 C 0.5503(5) 0.7813(4) 0.66637(14) 0.0593(8) Uani 1 1 d . . .
H14 H 0.5368 0.8761 0.6905 0.071 Uiso 1 1 calc R . .
C15 C 0.6259(4) 0.7818(4) 0.61179(13) 0.0546(7) Uani 1 1 d . . .
H15 H 0.6631 0.8767 0.5995 0.066 Uiso 1 1 calc R . .
N5 N 0.4724(5) 0.3496(4) 0.66942(14) 0.0707(8) Uani 1 1 d . . .
O1 O 0.5169(4) 0.2153(3) 0.63933(13) 0.0818(8) Uani 1 1 d . . .
O2 O 0.3927(8) 0.3596(6) 0.71625(16) 0.1391(16) Uani 1 1 d . . .
C21 C 0.8022(3) 0.1643(3) 0.06298(11) 0.0426(6) Uani 1 1 d . . .
N21 N 0.7262(3) 0.2361(3) 0.01190(10) 0.0418(5) Uani 1 1 d . . .
N22 N 0.5496(3) 0.2574(3) -0.00521(10) 0.0481(6) Uani 1 1 d . . .
C22 C 0.4587(4) 0.1952(4) 0.03232(12) 0.0475(6) Uani 1 1 d . . .
H22 H 0.3401 0.2046 0.0226 0.057 Uiso 1 1 calc R . .
C23 C 0.5205(4) 0.1132(3) 0.08749(12) 0.0443(6) Uani 1 1 d . . .
C24 C 0.6968(3) 0.1005(3) 0.10410(12) 0.0432(6) Uani 1 1 d . . .
C25 C 0.4106(4) 0.0486(4) 0.12418(13) 0.0529(7) Uani 1 1 d . . .
H25 H 0.2939 0.0564 0.1133 0.063 Uiso 1 1 calc R . .
C26 C 0.4764(4) -0.0268(4) 0.17657(14) 0.0588(8) Uani 1 1 d . . .
H26 H 0.4043 -0.0715 0.2013 0.071 Uiso 1 1 calc R . .
C27 C 0.6491(4) -0.0374(4) 0.19318(13) 0.0571(7) Uani 1 1 d . . .
H27 H 0.6907 -0.0880 0.2291 0.069 Uiso 1 1 calc R . .
C28 C 0.7595(4) 0.0254(4) 0.15774(13) 0.0510(7) Uani 1 1 d . . .
H28 H 0.8751 0.0180 0.1693 0.061 Uiso 1 1 calc R . .
N23 N 0.9730(3) 0.1647(3) 0.06417(10) 0.0501(6) Uani 1 1 d . . .
N24 N 1.0074(3) 0.2374(3) 0.01233(10) 0.0492(6) Uani 1 1 d . . .
C29 C 0.8590(3) 0.2802(3) -0.01918(12) 0.0432(6) Uani 1 1 d . . .
C30 C 0.8490(4) 0.3578(3) -0.07685(12) 0.0448(6) Uani 1 1 d . . .
C31 C 0.9859(4) 0.4205(4) -0.09678(12) 0.0458(6) Uani 1 1 d . . .
H31 H 1.0812 0.4116 -0.0737 0.055 Uiso 1 1 calc R . .
C32 C 0.9780(4) 0.4955(4) -0.15096(12) 0.0485(6) Uani 1 1 d . . .
C33 C 0.8414(4) 0.5121(4) -0.18695(13) 0.0542(7) Uani 1 1 d . . .
H33 H 0.8383 0.5661 -0.2234 0.065 Uiso 1 1 calc R . .
C34 C 0.7085(4) 0.4458(5) -0.16722(13) 0.0572(7) Uani 1 1 d . . .
H34 H 0.6163 0.4517 -0.1910 0.069 Uiso 1 1 calc R . .
C35 C 0.7108(4) 0.3714(4) -0.11292(12) 0.0514(7) Uani 1 1 d . . .
H35 H 0.6186 0.3295 -0.1001 0.062 Uiso 1 1 calc R . .
N25 N 1.1198(4) 0.5655(4) -0.17104(12) 0.0595(7) Uani 1 1 d . . .
O21 O 1.2720(3) 0.5020(4) -0.14796(12) 0.0723(7) Uani 1 1 d . . .
O22 O 1.0756(4) 0.6864(5) -0.20969(12) 0.0923(9) Uani 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
C1 N3 1.306(4) . ?
C1 N1 1.370(3) . ?
C1 C4 1.422(4) . ?
N1 C9 1.359(4) . ?
N1 N2 1.374(3) . ?
N2 C2 1.280(4) . ?
C2 C3 1.439(4) . ?
C2 H2 0.9300 . ?
C3 C5 1.381(4) . ?
C3 C4 1.402(4) . ?
C4 C8 1.392(4) . ?
C5 C6 1.374(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.378(5) . ?
C6 H6 0.9300 . ?
C7 C8 1.359(4) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
N3 N4 1.375(4) . ?
N4 C9 1.317(4) . ?
C9 C10 1.455(4) . ?
C10 C11 1.384(4) . ?
C10 C15 1.390(4) . ?
C11 C12 1.374(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.379(4) . ?
C12 N5 1.450(4) . ?
C13 C14 1.371(5) . ?
C13 H13 0.9300 . ?
C14 C15 1.371(4) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
N5 O1 1.205(4) . ?
N5 O2 1.209(4) . ?
C21 N23 1.319(3) . ?
C21 N21 1.359(3) . ?
C21 C24 1.421(4) . ?
N21 C29 1.364(3) . ?
N21 N22 1.385(3) . ?
N22 C22 1.287(4) . ?
C22 C23 1.433(4) . ?
C22 H22 0.9300 . ?
C23 C25 1.388(4) . ?
C23 C24 1.404(3) . ?
C24 C28 1.390(4) . ?
C25 C26 1.369(4) . ?
C25 H25 0.9300 . ?
C26 C27 1.385(4) . ?
C26 H26 0.9300 . ?
C27 C28 1.366(4) . ?
C27 H27 0.9300 . ?
C28 H28 0.9300 . ?
N23 N24 1.372(3) . ?
N24 C29 1.318(3) . ?
C29 C30 1.448(4) . ?
C30 C35 1.387(4) . ?
C30 C31 1.389(4) . ?
C31 C32 1.367(4) . ?
C31 H31 0.9300 . ?
C32 C33 1.368(4) . ?
C32 N25 1.463(4) . ?
C33 C34 1.380(4) . ?
C33 H33 0.9300 . ?
C34 C35 1.371(4) . ?
C34 H34 0.9300 . ?
C35 H35 0.9300 . ?
N25 O21 1.203(3) . ?
N25 O22 1.212(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
N3 C1 N1 109.7(3) . . ?
N3 C1 C4 131.5(3) . . ?
N1 C1 C4 118.8(2) . . ?
C9 N1 C1 106.4(2) . . ?
C9 N1 N2 127.1(2) . . ?
C1 N1 N2 126.6(2) . . ?
C2 N2 N1 113.5(2) . . ?
N2 C2 C3 127.0(3) . . ?
N2 C2 H2 116.5 . . ?
C3 C2 H2 116.5 . . ?
C5 C3 C4 119.7(3) . . ?
C5 C3 C2 122.1(3) . . ?
C4 C3 C2 118.1(3) . . ?
C8 C4 C3 119.6(3) . . ?
C8 C4 C1 124.6(3) . . ?
C3 C4 C1 115.9(3) . . ?
C6 C5 C3 119.7(3) . . ?
C6 C5 H5 120.2 . . ?
C3 C5 H5 120.2 . . ?
C5 C6 C7 120.4(3) . . ?
C5 C6 H6 119.8 . . ?
C7 C6 H6 119.8 . . ?
C8 C7 C6 121.0(3) . . ?
C8 C7 H7 119.5 . . ?
C6 C7 H7 119.5 . . ?
C7 C8 C4 119.6(3) . . ?
C7 C8 H8 120.2 . . ?
C4 C8 H8 120.2 . . ?
C1 N3 N4 106.8(2) . . ?
C9 N4 N3 109.2(2) . . ?
N4 C9 N1 107.9(3) . . ?
N4 C9 C10 123.7(3) . . ?
N1 C9 C10 128.3(3) . . ?
C11 C10 C15 118.6(3) . . ?
C11 C10 C9 117.8(3) . . ?
C15 C10 C9 123.6(3) . . ?
C12 C11 C10 119.0(3) . . ?
C12 C11 H11 120.5 . . ?
C10 C11 H11 120.5 . . ?
C11 C12 C13 122.9(3) . . ?
C11 C12 N5 118.3(3) . . ?
C13 C12 N5 118.8(3) . . ?
C14 C13 C12 117.5(3) . . ?
C14 C13 H13 121.3 . . ?
C12 C13 H13 121.3 . . ?
C13 C14 C15 121.1(3) . . ?
C13 C14 H14 119.5 . . ?
C15 C14 H14 119.5 . . ?
C14 C15 C10 121.0(3) . . ?
C14 C15 H15 119.5 . . ?
C10 C15 H15 119.5 . . ?
O1 N5 O2 122.8(3) . . ?
O1 N5 C12 118.6(3) . . ?
O2 N5 C12 118.6(3) . . ?
N23 C21 N21 109.7(2) . . ?
N23 C21 C24 131.2(2) . . ?
N21 C21 C24 119.1(2) . . ?
C21 N21 C29 106.5(2) . . ?
C21 N21 N22 126.4(2) . . ?
C29 N21 N22 127.0(2) . . ?
C22 N22 N21 113.3(2) . . ?
N22 C22 C23 127.0(2) . . ?
N22 C22 H22 116.5 . . ?
C23 C22 H22 116.5 . . ?
C25 C23 C24 120.1(3) . . ?
C25 C23 C22 121.8(2) . . ?
C24 C23 C22 118.1(2) . . ?
C28 C24 C23 119.8(3) . . ?
C28 C24 C21 124.2(2) . . ?
C23 C24 C21 116.0(2) . . ?
C26 C25 C23 119.1(3) . . ?
C26 C25 H25 120.5 . . ?
C23 C25 H25 120.5 . . ?
C25 C26 C27 120.8(3) . . ?
C25 C26 H26 119.6 . . ?
C27 C26 H26 119.6 . . ?
C28 C27 C26 121.1(3) . . ?
C28 C27 H27 119.4 . . ?
C26 C27 H27 119.4 . . ?
C27 C28 C24 119.1(3) . . ?
C27 C28 H28 120.4 . . ?
C24 C28 H28 120.4 . . ?
C21 N23 N24 106.7(2) . . ?
C29 N24 N23 109.1(2) . . ?
N24 C29 N21 108.0(2) . . ?
N24 C29 C30 123.6(2) . . ?
N21 C29 C30 128.4(2) . . ?
C35 C30 C31 118.8(3) . . ?
C35 C30 C29 123.3(3) . . ?
C31 C30 C29 118.0(3) . . ?
C32 C31 C30 118.8(3) . . ?
C32 C31 H31 120.6 . . ?
C30 C31 H31 120.6 . . ?
C31 C32 C33 123.3(3) . . ?
C31 C32 N25 118.3(3) . . ?
C33 C32 N25 118.4(3) . . ?
C32 C33 C34 117.6(3) . . ?
C32 C33 H33 121.2 . . ?
C34 C33 H33 121.2 . . ?
C35 C34 C33 120.8(3) . . ?
C35 C34 H34 119.6 . . ?
C33 C34 H34 119.6 . . ?
C34 C35 C30 120.7(3) . . ?
C34 C35 H35 119.6 . . ?
C30 C35 H35 119.6 . . ?
O21 N25 O22 123.8(3) . . ?
O21 N25 C32 118.4(3) . . ?
O22 N25 C32 117.8(3) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        67.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.265
_refine_diff_density_min         -0.309
_refine_diff_density_rms         0.069

####################################################################### 
# 
# 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_con82d
_database_code_depnum_ccdc_archive 'CCDC 1062224'
_audit_update_record             
;
2015-04-28 deposited with the CCDC.
2015-09-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL
_chemical_name_systematic        
'2-(4-nitrobenzylidene)-1-(phthalazin-1(2H)-ylidene)hydrazinium chloride methanol solvate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C15 H12 N5 O2 +), C H4 O, 2(Cl -)'
_chemical_formula_sum            'C31 H28 Cl2 N10 O5'
_chemical_formula_weight         691.53

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 '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/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

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

_cell_length_a                   6.8464(7)
_cell_length_b                   13.9346(11)
_cell_length_c                   16.3696(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.459(7)
_cell_angle_gamma                90.00
_cell_volume                     1554.6(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    100.0(1)
_cell_measurement_reflns_used    792
_cell_measurement_theta_min      2
_cell_measurement_theta_max      50

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.132
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.076
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.477
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             716
_exptl_absorpt_coefficient_mu    2.385
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2003)'
_exptl_absorpt_correction_T_min  0.775
_exptl_absorpt_correction_T_max  0.829
_exptl_special_details           ?

_diffrn_ambient_temperature      100.0(1)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         '30W microsource with MonoCap capillary'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEXII CCD  area-detector'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 19.67
_diffrn_standards_number         9
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  22.33
_diffrn_standards_decay_%        0.00
_diffrn_reflns_number            16703
_diffrn_reflns_av_R_equivalents  0.0193
_diffrn_reflns_av_sigmaI/netI    0.0125
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         4.17
_diffrn_reflns_theta_max         72.19
_reflns_number_total             3027
_reflns_number_gt                3021
_reflns_threshold_expression     >2sigma(I)

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

_computing_data_collection       'APEX2 (Bruker, 2010)'
_computing_cell_refinement       'SAINT-Plus (Bruker, 2009)'
_computing_data_reduction        'SAINT-Plus (Bruker, 2009)'
_computing_structure_solution    'SHELXS (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2008)'
_computing_molecular_graphics    
;XP in SHELXTL/PC (Sheldrick, 2008)
 ORTEP-3 W v. 1.062 (Farrugia 2012)
;
_computing_publication_material  
;SHELXL (Sheldrick, 2008) and
 PLATON (Spek, 2009)
;

_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     
'w=1/[σ²(Fo²)+(0.0356P)²+0.7815P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         3027
_refine_ls_number_parameters     223
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0278
_refine_ls_R_factor_gt           0.0278
_refine_ls_wR_factor_ref         0.0748
_refine_ls_wR_factor_gt          0.0748
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_restrained_S_all      1.080
_refine_ls_shift/su_max          0.001
_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 0.38742(4) 0.480292(19) 0.232383(18) 0.01987(10) Uani 1 1 d . . .
C1 C 0.22530(17) 0.75355(8) 0.28313(7) 0.0138(2) Uani 1 1 d . . .
N1 N 0.26282(15) 0.84699(7) 0.29285(6) 0.0158(2) Uani 1 1 d . . .
H1N H 0.3667 0.8746 0.2744 0.019 Uiso 1 1 d R . .
N2 N 0.15514(16) 0.91100(7) 0.33397(6) 0.0192(2) Uani 1 1 d . . .
C2 C 0.00117(18) 0.87663(9) 0.36397(7) 0.0184(2) Uani 1 1 d . . .
H2 H -0.0760 0.9195 0.3925 0.022 Uiso 1 1 calc R . .
C3 C -0.06092(17) 0.77835(9) 0.35710(7) 0.0152(2) Uani 1 1 d . . .
C4 C 0.05547(16) 0.71342(8) 0.31694(7) 0.0139(2) Uani 1 1 d . . .
C5 C -0.23128(17) 0.74559(9) 0.39001(7) 0.0172(2) Uani 1 1 d . . .
H5 H -0.3105 0.7891 0.4170 0.021 Uiso 1 1 calc R . .
C6 C -0.28283(17) 0.65025(9) 0.38304(7) 0.0173(2) Uani 1 1 d . . .
H6 H -0.3969 0.6279 0.4059 0.021 Uiso 1 1 calc R . .
C7 C -0.16748(18) 0.58602(9) 0.34235(7) 0.0172(2) Uani 1 1 d . . .
H7 H -0.2057 0.5206 0.3372 0.021 Uiso 1 1 calc R . .
C8 C 0.00095(17) 0.61634(9) 0.30962(7) 0.0159(2) Uani 1 1 d . . .
H8 H 0.0787 0.5722 0.2826 0.019 Uiso 1 1 calc R . .
N3 N 0.34405(14) 0.70017(7) 0.24131(6) 0.0145(2) Uani 1 1 d . . .
H3N H 0.3393 0.6358 0.2434 0.017 Uiso 1 1 d R . .
N4 N 0.48860(14) 0.74654(7) 0.20283(6) 0.0151(2) Uani 1 1 d . . .
C9 C 0.60983(17) 0.69040(9) 0.17157(7) 0.0156(2) Uani 1 1 d . . .
H9 H 0.5942 0.6229 0.1758 0.019 Uiso 1 1 calc R . .
C10 C 0.77232(17) 0.72901(9) 0.12939(7) 0.0152(2) Uani 1 1 d . . .
C11 C 0.79579(18) 0.82743(9) 0.11605(7) 0.0176(2) Uani 1 1 d . . .
H11 H 0.7021 0.8718 0.1328 0.021 Uiso 1 1 calc R . .
C12 C 0.95618(19) 0.86009(9) 0.07825(7) 0.0194(3) Uani 1 1 d . . .
H12 H 0.9734 0.9266 0.0685 0.023 Uiso 1 1 calc R . .
C13 C 1.09101(18) 0.79342(9) 0.05494(7) 0.0184(3) Uani 1 1 d . . .
C14 C 1.07146(18) 0.69564(9) 0.06672(7) 0.0185(2) Uani 1 1 d . . .
H14 H 1.1658 0.6518 0.0497 0.022 Uiso 1 1 calc R . .
C15 C 0.91000(18) 0.66366(9) 0.10414(7) 0.0174(2) Uani 1 1 d . . .
H15 H 0.8926 0.5969 0.1127 0.021 Uiso 1 1 calc R . .
N5 N 1.25986(16) 0.82759(9) 0.01351(7) 0.0239(2) Uani 1 1 d . . .
O1 O 1.28641(17) 0.91419(8) 0.00877(8) 0.0413(3) Uani 1 1 d . . .
O2 O 1.36490(14) 0.76715(8) -0.01517(6) 0.0300(2) Uani 1 1 d . . .
C91 C 0.5000 0.5000 0.0000 0.0342(5) Uani 1 2 d S . .
H91A H 0.5755 0.5586 0.0134 0.051 Uiso 0.50 1 d PR . .
H91B H 0.4624 0.4976 -0.0592 0.051 Uiso 0.50 1 d PR . .
H91C H 0.5804 0.4438 0.0165 0.051 Uiso 0.50 1 d PR . .
O91 O 0.3303(3) 0.49988(17) 0.04208(13) 0.0344(5) Uani 0.50 1 d P . .
H91O H 0.3552 0.4940 0.0978 0.052 Uiso 0.50 1 d PR . .


_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 N1 1.3337(15) . ?
C1 N3 1.3375(15) . ?
C1 C4 1.4468(16) . ?
N1 N2 1.3735(14) . ?
N1 H1N 0.8862 . ?
N2 C2 1.2962(16) . ?
C2 C3 1.4352(17) . ?
C2 H2 0.9500 . ?
C3 C5 1.4066(16) . ?
C3 C4 1.4091(16) . ?
C4 C8 1.4054(17) . ?
C5 C6 1.3766(18) . ?
C5 H5 0.9500 . ?
C6 C7 1.4030(17) . ?
C6 H6 0.9500 . ?
C7 C8 1.3830(17) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
N3 N4 1.3827(13) . ?
N3 H3N 0.8984 . ?
N4 C9 1.2821(16) . ?
C9 C10 1.4663(16) . ?
C9 H9 0.9500 . ?
C10 C11 1.4004(17) . ?
C10 C15 1.4010(17) . ?
C11 C12 1.3875(17) . ?
C11 H11 0.9500 . ?
C12 C13 1.3884(18) . ?
C12 H12 0.9500 . ?
C13 C14 1.3844(18) . ?
C13 N5 1.4738(15) . ?
C14 C15 1.3873(17) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
N5 O1 1.2239(16) . ?
N5 O2 1.2293(15) . ?
C91 O91 1.406(2) . ?
C91 O91 1.406(2) 3_665 ?
C91 H91A 0.9800 . ?
C91 H91B 0.9800 . ?
C91 H91C 0.9800 . ?
O91 H91O 0.9150 . ?

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
N1 C1 N3 118.98(10) . . ?
N1 C1 C4 118.97(10) . . ?
N3 C1 C4 122.05(10) . . ?
C1 N1 N2 125.89(10) . . ?
C1 N1 H1N 122.3 . . ?
N2 N1 H1N 111.7 . . ?
C2 N2 N1 116.07(10) . . ?
N2 C2 C3 124.64(11) . . ?
N2 C2 H2 117.7 . . ?
C3 C2 H2 117.7 . . ?
C5 C3 C4 119.78(11) . . ?
C5 C3 C2 122.00(11) . . ?
C4 C3 C2 118.22(11) . . ?
C8 C4 C3 120.03(11) . . ?
C8 C4 C1 123.78(11) . . ?
C3 C4 C1 116.17(11) . . ?
C6 C5 C3 119.79(11) . . ?
C6 C5 H5 120.1 . . ?
C3 C5 H5 120.1 . . ?
C5 C6 C7 120.23(11) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 H6 119.9 . . ?
C8 C7 C6 121.12(11) . . ?
C8 C7 H7 119.4 . . ?
C6 C7 H7 119.4 . . ?
C7 C8 C4 119.04(11) . . ?
C7 C8 H8 120.5 . . ?
C4 C8 H8 120.5 . . ?
C1 N3 N4 118.00(10) . . ?
C1 N3 H3N 120.7 . . ?
N4 N3 H3N 120.9 . . ?
C9 N4 N3 114.54(10) . . ?
N4 C9 C10 120.87(11) . . ?
N4 C9 H9 119.6 . . ?
C10 C9 H9 119.6 . . ?
C11 C10 C15 120.00(11) . . ?
C11 C10 C9 122.44(11) . . ?
C15 C10 C9 117.54(11) . . ?
C12 C11 C10 119.89(11) . . ?
C12 C11 H11 120.1 . . ?
C10 C11 H11 120.1 . . ?
C11 C12 C13 118.56(11) . . ?
C11 C12 H12 120.7 . . ?
C13 C12 H12 120.7 . . ?
C14 C13 C12 123.00(11) . . ?
C14 C13 N5 118.20(11) . . ?
C12 C13 N5 118.78(11) . . ?
C13 C14 C15 117.99(11) . . ?
C13 C14 H14 121.0 . . ?
C15 C14 H14 121.0 . . ?
C14 C15 C10 120.55(12) . . ?
C14 C15 H15 119.7 . . ?
C10 C15 H15 119.7 . . ?
O1 N5 O2 123.74(11) . . ?
O1 N5 C13 118.39(11) . . ?
O2 N5 C13 117.87(11) . . ?
O91 C91 O91 180.00(14) . 3_665 ?
O91 C91 H91A 109.5 . . ?
O91 C91 H91A 70.5 3_665 . ?
O91 C91 H91B 109.5 . . ?
O91 C91 H91B 70.5 3_665 . ?
H91A C91 H91B 109.5 . . ?
O91 C91 H91C 109.4 . . ?
O91 C91 H91C 70.6 3_665 . ?
H91A C91 H91C 109.5 . . ?
H91B C91 H91C 109.5 . . ?
C91 O91 H91O 113.8 . . ?

_diffrn_measured_fraction_theta_max 0.983
_diffrn_reflns_theta_full        67.00
_diffrn_measured_fraction_theta_full 0.985
_refine_diff_density_max         0.224
_refine_diff_density_min         -0.277
_refine_diff_density_rms         0.047

####################################################################### 
# 
# 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_con82
_database_code_depnum_ccdc_archive 'CCDC 1062225'
_audit_update_record             
;
2015-04-28 deposited with the CCDC.
2015-09-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL
_chemical_name_systematic        
; 
2-(4-nitrobenzylidene)-1-(phthalazin-1(2H)-ylidene)hydrazine
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H11 N5 O2'
_chemical_formula_sum            'C15 H11 N5 O2'
_chemical_formula_weight         293.29

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

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

_cell_length_a                   14.9193(4)
_cell_length_b                   3.80140(10)
_cell_length_c                   23.8964(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 107.1950(10)
_cell_angle_gamma                90.00
_cell_volume                     1294.69(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    100.0(1)
_cell_measurement_reflns_used    1308
_cell_measurement_theta_min      2
_cell_measurement_theta_max      50

_exptl_crystal_description       prism
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.505
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             608
_exptl_absorpt_coefficient_mu    0.874
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2003)'
_exptl_absorpt_correction_T_min  0.879
_exptl_absorpt_correction_T_max  0.914
_exptl_special_details           ?

_diffrn_ambient_temperature      100.0(1)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         '30W microsource with MonoCap capillary'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEXII CCD area-detector'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 12.8
_diffrn_standards_number         11
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  11.67
_diffrn_standards_decay_%        0.00
_diffrn_reflns_number            14195
_diffrn_reflns_av_R_equivalents  0.0193
_diffrn_reflns_av_sigmaI/netI    0.0132
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       3
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         3.10
_diffrn_reflns_theta_max         74.54
_reflns_number_total             2639
_reflns_number_gt                2432
_reflns_threshold_expression     >2sigma(I)

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

_computing_data_collection       'APEX2 (Bruker, 2010)'
_computing_cell_refinement       'SAINT-Plus (Bruker, 2009)'
_computing_data_reduction        'SAINT-Plus (Bruker, 2009)'
_computing_structure_solution    'SHELXS (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2008)'
_computing_molecular_graphics    
;XP in SHELXTL/PC (Sheldrick, 2008)
 ORTEP-3 W v. 1.062 (Farrugia 2012)
;
_computing_publication_material  
;SHELXL (Sheldrick, 2008) and
 PLATON (Spek, 2009)
;

_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     
'w=1/[σ²(Fo²)+(0.0591P)²+0.3722P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2639
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0351
_refine_ls_R_factor_gt           0.0330
_refine_ls_wR_factor_ref         0.0979
_refine_ls_wR_factor_gt          0.0957
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_refine_ls_shift/su_max          0.001
_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 0.11102(7) 1.0914(3) 0.43282(4) 0.0150(2) Uani 1 1 d . . .
N1 N 0.06487(6) 1.2628(2) 0.46633(4) 0.0170(2) Uani 1 1 d . . .
H1N H 0.0029 1.3213 0.4511 0.020 Uiso 1 1 d R . .
N2 N 0.10122(6) 1.3556(2) 0.52394(4) 0.0180(2) Uani 1 1 d . . .
C2 C 0.18806(7) 1.2767(3) 0.54927(4) 0.0180(2) Uani 1 1 d . . .
H2 H 0.2137 1.3353 0.5895 0.022 Uiso 1 1 calc R . .
C3 C 0.24846(7) 1.1056(3) 0.52049(4) 0.0161(2) Uani 1 1 d . . .
C4 C 0.20976(7) 1.0139(3) 0.46124(4) 0.0151(2) Uani 1 1 d . . .
C5 C 0.34314(7) 1.0318(3) 0.54917(4) 0.0189(2) Uani 1 1 d . . .
H5 H 0.3695 1.0902 0.5893 0.023 Uiso 1 1 calc R . .
C6 C 0.39759(7) 0.8740(3) 0.51870(5) 0.0203(2) Uani 1 1 d . . .
H6 H 0.4618 0.8254 0.5380 0.024 Uiso 1 1 calc R . .
C7 C 0.35912(7) 0.7848(3) 0.45957(4) 0.0194(2) Uani 1 1 d . . .
H7 H 0.3975 0.6785 0.4389 0.023 Uiso 1 1 calc R . .
C8 C 0.26559(7) 0.8503(3) 0.43104(4) 0.0171(2) Uani 1 1 d . . .
H8 H 0.2394 0.7846 0.3912 0.021 Uiso 1 1 calc R . .
N3 N 0.07262(6) 0.9924(2) 0.37836(4) 0.0169(2) Uani 1 1 d . . .
N4 N -0.02264(6) 1.0680(2) 0.35846(4) 0.0169(2) Uani 1 1 d . . .
C9 C -0.06059(7) 0.9479(3) 0.30659(4) 0.0169(2) Uani 1 1 d . . .
H9 H -0.0221 0.8317 0.2870 0.020 Uiso 1 1 calc R . .
C10 C -0.16088(7) 0.9839(3) 0.27666(4) 0.0159(2) Uani 1 1 d . . .
C11 C -0.22280(7) 1.1389(3) 0.30382(4) 0.0173(2) Uani 1 1 d . . .
H11 H -0.1992 1.2237 0.3428 0.021 Uiso 1 1 calc R . .
C12 C -0.31745(7) 1.1700(3) 0.27464(4) 0.0180(2) Uani 1 1 d . . .
H12 H -0.3591 1.2773 0.2929 0.022 Uiso 1 1 calc R . .
C13 C -0.34984(7) 1.0393(3) 0.21777(4) 0.0176(2) Uani 1 1 d . . .
C14 C -0.29116(7) 0.8799(3) 0.18995(4) 0.0182(2) Uani 1 1 d . . .
H14 H -0.3156 0.7892 0.1514 0.022 Uiso 1 1 calc R . .
C15 C -0.19622(7) 0.8552(3) 0.21937(4) 0.0177(2) Uani 1 1 d . . .
H15 H -0.1549 0.7506 0.2006 0.021 Uiso 1 1 calc R . .
N5 N -0.44958(6) 1.0757(3) 0.18514(4) 0.0217(2) Uani 1 1 d . . .
O1 O -0.49891(6) 1.2622(3) 0.20541(4) 0.0346(2) Uani 1 1 d . . .
O2 O -0.47904(6) 0.9187(3) 0.13841(4) 0.0363(2) Uani 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
C1 N3 1.3125(13) . ?
C1 N1 1.3660(12) . ?
C1 C4 1.4582(13) . ?
N1 N2 1.3685(11) . ?
N1 H1N 0.9158 . ?
N2 C2 1.2928(13) . ?
C2 C3 1.4402(13) . ?
C2 H2 0.9500 . ?
C3 C5 1.4041(14) . ?
C3 C4 1.4058(13) . ?
C4 C8 1.3988(13) . ?
C5 C6 1.3781(15) . ?
C5 H5 0.9500 . ?
C6 C7 1.4005(15) . ?
C6 H6 0.9500 . ?
C7 C8 1.3826(14) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
N3 N4 1.3889(11) . ?
N4 C9 1.2845(13) . ?
C9 C10 1.4617(13) . ?
C9 H9 0.9500 . ?
C10 C15 1.4016(13) . ?
C10 C11 1.4058(14) . ?
C11 C12 1.3827(14) . ?
C11 H11 0.9500 . ?
C12 C13 1.3925(14) . ?
C12 H12 0.9500 . ?
C13 C14 1.3854(14) . ?
C13 N5 1.4680(12) . ?
C14 C15 1.3859(14) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
N5 O1 1.2206(12) . ?
N5 O2 1.2272(12) . ?

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
N3 C1 N1 124.76(9) . . ?
N3 C1 C4 119.25(9) . . ?
N1 C1 C4 115.99(8) . . ?
C1 N1 N2 126.46(8) . . ?
C1 N1 H1N 120.5 . . ?
N2 N1 H1N 113.0 . . ?
C2 N2 N1 117.09(8) . . ?
N2 C2 C3 124.28(9) . . ?
N2 C2 H2 117.9 . . ?
C3 C2 H2 117.9 . . ?
C5 C3 C4 119.76(9) . . ?
C5 C3 C2 122.58(9) . . ?
C4 C3 C2 117.66(9) . . ?
C8 C4 C3 119.99(9) . . ?
C8 C4 C1 121.55(9) . . ?
C3 C4 C1 118.46(9) . . ?
C6 C5 C3 119.62(9) . . ?
C6 C5 H5 120.2 . . ?
C3 C5 H5 120.2 . . ?
C5 C6 C7 120.57(9) . . ?
C5 C6 H6 119.7 . . ?
C7 C6 H6 119.7 . . ?
C8 C7 C6 120.44(9) . . ?
C8 C7 H7 119.8 . . ?
C6 C7 H7 119.8 . . ?
C7 C8 C4 119.59(9) . . ?
C7 C8 H8 120.2 . . ?
C4 C8 H8 120.2 . . ?
C1 N3 N4 112.50(8) . . ?
C9 N4 N3 111.80(8) . . ?
N4 C9 C10 122.30(9) . . ?
N4 C9 H9 118.9 . . ?
C10 C9 H9 118.9 . . ?
C15 C10 C11 119.23(9) . . ?
C15 C10 C9 118.71(9) . . ?
C11 C10 C9 122.05(9) . . ?
C12 C11 C10 121.03(9) . . ?
C12 C11 H11 119.5 . . ?
C10 C11 H11 119.5 . . ?
C11 C12 C13 118.01(9) . . ?
C11 C12 H12 121.0 . . ?
C13 C12 H12 121.0 . . ?
C14 C13 C12 122.55(9) . . ?
C14 C13 N5 118.13(9) . . ?
C12 C13 N5 119.31(9) . . ?
C13 C14 C15 118.84(9) . . ?
C13 C14 H14 120.6 . . ?
C15 C14 H14 120.6 . . ?
C14 C15 C10 120.31(9) . . ?
C14 C15 H15 119.8 . . ?
C10 C15 H15 119.8 . . ?
O1 N5 O2 123.21(9) . . ?
O1 N5 C13 118.65(9) . . ?
O2 N5 C13 118.14(9) . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        67.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.221
_refine_diff_density_min         -0.259
_refine_diff_density_rms         0.044

####################################################################### 
# 
# 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_con82b
_database_code_depnum_ccdc_archive 'CCDC 1062226'
_audit_update_record             
;
2015-04-28 deposited with the CCDC.
2015-09-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL
_chemical_name_systematic        
; 
3-(4-nitrophenyl)[1,2,4]triazolo[3,4-a]phthalazine
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H9 N5 O2'
_chemical_formula_sum            'C15 H9 N5 O2'
_chemical_formula_weight         291.27

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.0341(9)
_cell_length_b                   7.3760(9)
_cell_length_c                   12.4146(11)
_cell_angle_alpha                79.762(6)
_cell_angle_beta                 79.663(9)
_cell_angle_gamma                78.553(9)
_cell_volume                     614.27(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    100.0(1)
_cell_measurement_reflns_used    1095
_cell_measurement_theta_min      2
_cell_measurement_theta_max      50

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.17
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.575
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             300
_exptl_absorpt_coefficient_mu    0.921
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2003)'
_exptl_absorpt_correction_T_min  0.852
_exptl_absorpt_correction_T_max  0.860
_exptl_special_details           ?

_diffrn_ambient_temperature      100.0(1)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         '30W microsource with MonoCap capillary'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEXII CCD area-detector'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 12.8
_diffrn_standards_number         7
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  15.00
_diffrn_standards_decay_%        0.00
_diffrn_reflns_number            6971
_diffrn_reflns_av_R_equivalents  0.0160
_diffrn_reflns_av_sigmaI/netI    0.0153
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.66
_diffrn_reflns_theta_max         70.01
_reflns_number_total             2238
_reflns_number_gt                2074
_reflns_threshold_expression     >2sigma(I)

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

_computing_data_collection       'APEX2 (Bruker, 2010)'
_computing_cell_refinement       'SAINT-Plus (Bruker, 2009)'
_computing_data_reduction        'SAINT-Plus (Bruker, 2009)'
_computing_structure_solution    'SHELXS (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2008)'
_computing_molecular_graphics    
;XP in SHELXTL/PC (Sheldrick, 2008)
 ORTEP-3 W v. 1.062 (Farrugia 2012)
;
_computing_publication_material  
;SHELXL (Sheldrick, 2008) and
 PLATON (Spek, 2009)
;

_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)+(0.0554P)²+0.2342P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2238
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0381
_refine_ls_R_factor_gt           0.0357
_refine_ls_wR_factor_ref         0.1017
_refine_ls_wR_factor_gt          0.0978
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_restrained_S_all      1.074
_refine_ls_shift/su_max          0.001
_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 -0.21275(18) 1.07371(19) 0.92548(11) 0.0211(3) Uani 1 1 d . . .
N1 N -0.14730(15) 0.90175(16) 0.89162(9) 0.0203(3) Uani 1 1 d . . .
N2 N -0.14508(17) 0.72875(16) 0.95710(9) 0.0242(3) Uani 1 1 d . . .
C2 C -0.2219(2) 0.7388(2) 1.05959(11) 0.0268(3) Uani 1 1 d . . .
H2 H -0.2232 0.6238 1.1082 0.032 Uiso 1 1 calc R . .
C3 C -0.30589(19) 0.9080(2) 1.10716(11) 0.0257(3) Uani 1 1 d . . .
C4 C -0.29759(18) 1.0820(2) 1.03918(11) 0.0231(3) Uani 1 1 d . . .
C5 C -0.3943(2) 0.9044(2) 1.21832(12) 0.0299(3) Uani 1 1 d . . .
H5 H -0.4027 0.7885 1.2650 0.036 Uiso 1 1 calc R . .
C6 C -0.4680(2) 1.0693(2) 1.25881(12) 0.0312(3) Uani 1 1 d . . .
H6 H -0.5283 1.0667 1.3338 0.037 Uiso 1 1 calc R . .
C7 C -0.4562(2) 1.2423(2) 1.19139(13) 0.0317(4) Uani 1 1 d . . .
H7 H -0.5068 1.3551 1.2214 0.038 Uiso 1 1 calc R . .
C8 C -0.37110(19) 1.2493(2) 1.08127(12) 0.0275(3) Uani 1 1 d . . .
H8 H -0.3631 1.3660 1.0354 0.033 Uiso 1 1 calc R . .
N3 N -0.18629(16) 1.20863(16) 0.84190(9) 0.0242(3) Uani 1 1 d . . .
N4 N -0.10121(16) 1.12243(16) 0.75094(9) 0.0238(3) Uani 1 1 d . . .
C9 C -0.07758(18) 0.93915(19) 0.78068(11) 0.0211(3) Uani 1 1 d . . .
C10 C 0.01176(18) 0.80562(19) 0.70403(11) 0.0208(3) Uani 1 1 d . . .
C11 C -0.00906(19) 0.61678(19) 0.72495(11) 0.0228(3) Uani 1 1 d . . .
H11 H -0.0853 0.5697 0.7914 0.027 Uiso 1 1 calc R . .
C12 C 0.08204(19) 0.49893(19) 0.64820(11) 0.0240(3) Uani 1 1 d . . .
H12 H 0.0691 0.3708 0.6613 0.029 Uiso 1 1 calc R . .
C13 C 0.19196(18) 0.57193(19) 0.55233(11) 0.0229(3) Uani 1 1 d . . .
C14 C 0.20987(19) 0.75929(19) 0.52769(11) 0.0231(3) Uani 1 1 d . . .
H14 H 0.2822 0.8062 0.4597 0.028 Uiso 1 1 calc R . .
C15 C 0.11998(19) 0.87569(19) 0.60436(11) 0.0224(3) Uani 1 1 d . . .
H15 H 0.1314 1.0043 0.5896 0.027 Uiso 1 1 calc R . .
N5 N 0.29758(16) 0.44661(17) 0.47315(9) 0.0243(3) Uani 1 1 d . . .
O1 O 0.28778(15) 0.27864(14) 0.49656(9) 0.0320(3) Uani 1 1 d . . .
O2 O 0.39318(14) 0.51453(15) 0.38776(8) 0.0295(3) Uani 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
C1 N3 1.3187(18) . ?
C1 N1 1.3732(18) . ?
C1 C4 1.4374(19) . ?
N1 C9 1.3747(17) . ?
N1 N2 1.3847(15) . ?
N2 C2 1.2991(18) . ?
C2 C3 1.449(2) . ?
C2 H2 0.9500 . ?
C3 C5 1.4061(19) . ?
C3 C4 1.410(2) . ?
C4 C8 1.394(2) . ?
C5 C6 1.369(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.405(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.387(2) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
N3 N4 1.3781(16) . ?
N4 C9 1.3217(18) . ?
C9 C10 1.4640(19) . ?
C10 C11 1.4028(19) . ?
C10 C15 1.4030(18) . ?
C11 C12 1.389(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.3826(19) . ?
C12 H12 0.9500 . ?
C13 C14 1.387(2) . ?
C13 N5 1.4701(18) . ?
C14 C15 1.3790(19) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
N5 O2 1.2313(15) . ?
N5 O1 1.2340(16) . ?

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
N3 C1 N1 110.58(12) . . ?
N3 C1 C4 130.61(13) . . ?
N1 C1 C4 118.80(12) . . ?
C1 N1 C9 105.23(11) . . ?
C1 N1 N2 126.89(11) . . ?
C9 N1 N2 127.83(11) . . ?
C2 N2 N1 113.42(12) . . ?
N2 C2 C3 126.47(13) . . ?
N2 C2 H2 116.8 . . ?
C3 C2 H2 116.8 . . ?
C5 C3 C4 119.15(14) . . ?
C5 C3 C2 122.33(14) . . ?
C4 C3 C2 118.52(12) . . ?
C8 C4 C3 121.01(13) . . ?
C8 C4 C1 123.22(13) . . ?
C3 C4 C1 115.76(13) . . ?
C6 C5 C3 119.51(14) . . ?
C6 C5 H5 120.2 . . ?
C3 C5 H5 120.2 . . ?
C5 C6 C7 121.16(14) . . ?
C5 C6 H6 119.4 . . ?
C7 C6 H6 119.4 . . ?
C8 C7 C6 120.35(14) . . ?
C8 C7 H7 119.8 . . ?
C6 C7 H7 119.8 . . ?
C7 C8 C4 118.80(14) . . ?
C7 C8 H8 120.6 . . ?
C4 C8 H8 120.6 . . ?
C1 N3 N4 106.41(11) . . ?
C9 N4 N3 109.11(11) . . ?
N4 C9 N1 108.68(12) . . ?
N4 C9 C10 123.25(12) . . ?
N1 C9 C10 128.07(12) . . ?
C11 C10 C15 119.87(13) . . ?
C11 C10 C9 123.45(12) . . ?
C15 C10 C9 116.67(12) . . ?
C12 C11 C10 119.81(12) . . ?
C12 C11 H11 120.1 . . ?
C10 C11 H11 120.1 . . ?
C13 C12 C11 118.64(13) . . ?
C13 C12 H12 120.7 . . ?
C11 C12 H12 120.7 . . ?
C12 C13 C14 122.84(13) . . ?
C12 C13 N5 119.17(12) . . ?
C14 C13 N5 117.98(12) . . ?
C15 C14 C13 118.30(12) . . ?
C15 C14 H14 120.8 . . ?
C13 C14 H14 120.8 . . ?
C14 C15 C10 120.48(13) . . ?
C14 C15 H15 119.8 . . ?
C10 C15 H15 119.8 . . ?
O2 N5 O1 123.55(12) . . ?
O2 N5 C13 118.22(12) . . ?
O1 N5 C13 118.23(11) . . ?

_diffrn_measured_fraction_theta_max 0.963
_diffrn_reflns_theta_full        67.00
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.301
_refine_diff_density_min         -0.296
_refine_diff_density_rms         0.046

####################################################################### 
# 
# 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_con83
_database_code_depnum_ccdc_archive 'CCDC 1062227'
_audit_update_record             
;
2015-04-28 deposited with the CCDC.
2015-09-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL
_chemical_name_systematic        
'2-[3-(4-nitrophenyl)prop-2-en-1-ylidene]-1-(phthalazin-1(2H)-ylidene)hydrazinium chloride methanol solvate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H14 N5 O2 +, C H4 O, Cl -'
_chemical_formula_sum            'C18 H18 Cl N5 O3'
_chemical_formula_weight         387.82

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.7747(5)
_cell_length_b                   9.9551(6)
_cell_length_c                   12.0764(9)
_cell_angle_alpha                99.836(4)
_cell_angle_beta                 102.862(4)
_cell_angle_gamma                91.510(5)
_cell_volume                     895.82(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    100.0(1)
_cell_measurement_reflns_used    1914
_cell_measurement_theta_min      2
_cell_measurement_theta_max      50

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.19
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.438
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             404
_exptl_absorpt_coefficient_mu    2.154
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2003)'
_exptl_absorpt_correction_T_min  0.621
_exptl_absorpt_correction_T_max  0.668
_exptl_special_details           ?

_diffrn_ambient_temperature      100.0(1)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         '30W microsource with MonoCap capillary'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEXII CCD area-detector'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 12.8
_diffrn_standards_number         7
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  22.33
_diffrn_standards_decay_%        0.00
_diffrn_reflns_number            9747
_diffrn_reflns_av_R_equivalents  0.0219
_diffrn_reflns_av_sigmaI/netI    0.0213
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.82
_diffrn_reflns_theta_max         72.30
_reflns_number_total             3369
_reflns_number_gt                3364
_reflns_threshold_expression     >2sigma(I)

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

_computing_data_collection       'APEX2 (Bruker, 2010)'
_computing_cell_refinement       'SAINT-Plus (Bruker, 2009)'
_computing_data_reduction        'SAINT-Plus (Bruker, 2009)'
_computing_structure_solution    'SHELXS (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2008)'
_computing_molecular_graphics    
;XP in SHELXTL/PC (Sheldrick, 2008)
 ORTEP-3 W v. 1.062 (Farrugia 2012)
;
_computing_publication_material  
;SHELXL (Sheldrick, 2008) and
 PLATON (Spek, 2009)
;

_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     
'w=1/[σ²(Fo²)+(0.0403P)²+0.3785P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0163(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3369
_refine_ls_number_parameters     246
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0283
_refine_ls_R_factor_gt           0.0283
_refine_ls_wR_factor_ref         0.0790
_refine_ls_wR_factor_gt          0.0790
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_refine_ls_shift/su_max          0.001
_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 0.04724(4) 0.17938(3) 0.77227(2) 0.01978(11) Uani 1 1 d . . .
C1 C 0.18963(15) -0.21169(12) 0.66616(10) 0.0155(2) Uani 1 1 d . . .
N1 N 0.21515(13) -0.31346(10) 0.58495(9) 0.0176(2) Uani 1 1 d . . .
H1N H 0.2293 -0.2987 0.5160 0.021 Uiso 1 1 d R . .
N2 N 0.21566(14) -0.44952(11) 0.59300(9) 0.0204(2) Uani 1 1 d . . .
C2 C 0.18741(16) -0.48047(13) 0.68780(11) 0.0202(3) Uani 1 1 d . . .
H2 H 0.1873 -0.5739 0.6953 0.024 Uiso 1 1 calc R . .
C3 C 0.15644(15) -0.38281(13) 0.78189(10) 0.0174(2) Uani 1 1 d . . .
C4 C 0.15748(15) -0.24406(12) 0.77225(10) 0.0157(2) Uani 1 1 d . . .
C5 C 0.12753(16) -0.42282(13) 0.88297(11) 0.0201(3) Uani 1 1 d . . .
H5 H 0.1270 -0.5164 0.8900 0.024 Uiso 1 1 calc R . .
C6 C 0.10014(16) -0.32515(14) 0.97144(11) 0.0210(3) Uani 1 1 d . . .
H6 H 0.0811 -0.3515 1.0400 0.025 Uiso 1 1 calc R . .
C7 C 0.10001(16) -0.18694(13) 0.96136(10) 0.0201(3) Uani 1 1 d . . .
H7 H 0.0802 -0.1208 1.0231 0.024 Uiso 1 1 calc R . .
C8 C 0.12825(16) -0.14535(13) 0.86300(10) 0.0184(3) Uani 1 1 d . . .
H8 H 0.1279 -0.0515 0.8569 0.022 Uiso 1 1 calc R . .
N3 N 0.19546(13) -0.08294(10) 0.64735(8) 0.0168(2) Uani 1 1 d . . .
H3N H 0.1644 -0.0113 0.6967 0.020 Uiso 1 1 d R . .
N4 N 0.23004(13) -0.06299(11) 0.54388(8) 0.0182(2) Uani 1 1 d . . .
C9 C 0.22687(16) 0.06038(12) 0.52484(10) 0.0171(2) Uani 1 1 d . . .
H9 H 0.2019 0.1337 0.5792 0.021 Uiso 1 1 calc R . .
C10 C 0.26313(16) 0.08174(13) 0.41666(10) 0.0183(3) Uani 1 1 d . . .
H10 H 0.2813 0.0030 0.3650 0.022 Uiso 1 1 calc R . .
C11 C 0.27349(16) 0.20229(12) 0.38235(10) 0.0176(2) Uani 1 1 d . . .
H11 H 0.2548 0.2822 0.4326 0.021 Uiso 1 1 calc R . .
C12 C 0.31221(15) 0.21760(12) 0.27119(10) 0.0162(2) Uani 1 1 d . . .
C13 C 0.32255(16) 0.34765(12) 0.24205(10) 0.0183(3) Uani 1 1 d . . .
H13 H 0.3038 0.4254 0.2946 0.022 Uiso 1 1 calc R . .
C14 C 0.35970(16) 0.36499(13) 0.13767(11) 0.0185(3) Uani 1 1 d . . .
H14 H 0.3669 0.4534 0.1186 0.022 Uiso 1 1 calc R . .
C15 C 0.38595(15) 0.25018(13) 0.06232(10) 0.0164(2) Uani 1 1 d . . .
C16 C 0.37462(16) 0.11987(13) 0.08774(10) 0.0185(3) Uani 1 1 d . . .
H16 H 0.3913 0.0425 0.0341 0.022 Uiso 1 1 calc R . .
C17 C 0.33883(17) 0.10418(13) 0.19196(11) 0.0192(3) Uani 1 1 d . . .
H17 H 0.3322 0.0154 0.2102 0.023 Uiso 1 1 calc R . .
N5 N 0.43012(13) 0.26476(11) -0.04742(9) 0.0183(2) Uani 1 1 d . . .
O1 O 0.42115(12) 0.37709(9) -0.07643(8) 0.0232(2) Uani 1 1 d . . .
O2 O 0.47582(13) 0.16359(10) -0.10471(8) 0.0259(2) Uani 1 1 d . . .
O91 O 0.23801(11) -0.33499(9) 0.36025(7) 0.0201(2) Uani 1 1 d . . .
H91O H 0.1503 -0.2933 0.3237 0.030 Uiso 1 1 d R . .
C91 C 0.39737(18) -0.29169(14) 0.33231(12) 0.0272(3) Uani 1 1 d . . .
H91A H 0.4363 -0.1988 0.3744 0.041 Uiso 1 1 calc R . .
H91B H 0.3757 -0.2927 0.2491 0.041 Uiso 1 1 calc R . .
H91C H 0.4894 -0.3539 0.3543 0.041 Uiso 1 1 calc R . .


_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 N1 1.3362(15) . ?
C1 N3 1.3406(16) . ?
C1 C4 1.4447(16) . ?
N1 N2 1.3745(15) . ?
N1 H1N 0.8989 . ?
N2 C2 1.2972(16) . ?
C2 C3 1.4321(17) . ?
C2 H2 0.9500 . ?
C3 C4 1.4058(17) . ?
C3 C5 1.4081(17) . ?
C4 C8 1.4047(17) . ?
C5 C6 1.3746(18) . ?
C5 H5 0.9500 . ?
C6 C7 1.4018(18) . ?
C6 H6 0.9500 . ?
C7 C8 1.3820(17) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
N3 N4 1.3801(13) . ?
N3 H3N 0.9222 . ?
N4 C9 1.2874(16) . ?
C9 C10 1.4448(16) . ?
C9 H9 0.9500 . ?
C10 C11 1.3409(17) . ?
C10 H10 0.9500 . ?
C11 C12 1.4709(16) . ?
C11 H11 0.9500 . ?
C12 C17 1.4016(17) . ?
C12 C13 1.4032(17) . ?
C13 C14 1.3914(17) . ?
C13 H13 0.9500 . ?
C14 C15 1.3841(17) . ?
C14 H14 0.9500 . ?
C15 C16 1.3881(17) . ?
C15 N5 1.4700(15) . ?
C16 C17 1.3809(17) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
N5 O1 1.2269(14) . ?
N5 O2 1.2286(14) . ?
O91 C91 1.4291(15) . ?
O91 H91O 0.8807 . ?
C91 H91A 0.9800 . ?
C91 H91B 0.9800 . ?
C91 H91C 0.9800 . ?

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
N1 C1 N3 119.31(10) . . ?
N1 C1 C4 118.73(11) . . ?
N3 C1 C4 121.96(11) . . ?
C1 N1 N2 125.69(10) . . ?
C1 N1 H1N 121.8 . . ?
N2 N1 H1N 112.5 . . ?
C2 N2 N1 116.43(10) . . ?
N2 C2 C3 124.21(12) . . ?
N2 C2 H2 117.9 . . ?
C3 C2 H2 117.9 . . ?
C4 C3 C5 120.00(11) . . ?
C4 C3 C2 118.48(11) . . ?
C5 C3 C2 121.51(12) . . ?
C8 C4 C3 120.06(11) . . ?
C8 C4 C1 123.49(11) . . ?
C3 C4 C1 116.45(11) . . ?
C6 C5 C3 119.37(12) . . ?
C6 C5 H5 120.3 . . ?
C3 C5 H5 120.3 . . ?
C5 C6 C7 120.55(11) . . ?
C5 C6 H6 119.7 . . ?
C7 C6 H6 119.7 . . ?
C8 C7 C6 121.06(11) . . ?
C8 C7 H7 119.5 . . ?
C6 C7 H7 119.5 . . ?
C7 C8 C4 118.96(11) . . ?
C7 C8 H8 120.5 . . ?
C4 C8 H8 120.5 . . ?
C1 N3 N4 117.30(10) . . ?
C1 N3 H3N 121.9 . . ?
N4 N3 H3N 120.4 . . ?
C9 N4 N3 116.50(10) . . ?
N4 C9 C10 116.68(11) . . ?
N4 C9 H9 121.7 . . ?
C10 C9 H9 121.7 . . ?
C11 C10 C9 126.12(11) . . ?
C11 C10 H10 116.9 . . ?
C9 C10 H10 116.9 . . ?
C10 C11 C12 123.60(11) . . ?
C10 C11 H11 118.2 . . ?
C12 C11 H11 118.2 . . ?
C17 C12 C13 118.42(11) . . ?
C17 C12 C11 121.42(11) . . ?
C13 C12 C11 120.16(11) . . ?
C14 C13 C12 121.30(11) . . ?
C14 C13 H13 119.4 . . ?
C12 C13 H13 119.4 . . ?
C15 C14 C13 118.30(11) . . ?
C15 C14 H14 120.9 . . ?
C13 C14 H14 120.9 . . ?
C14 C15 C16 121.93(11) . . ?
C14 C15 N5 119.87(11) . . ?
C16 C15 N5 118.19(11) . . ?
C17 C16 C15 119.18(11) . . ?
C17 C16 H16 120.4 . . ?
C15 C16 H16 120.4 . . ?
C16 C17 C12 120.86(11) . . ?
C16 C17 H17 119.6 . . ?
C12 C17 H17 119.6 . . ?
O1 N5 O2 123.50(10) . . ?
O1 N5 C15 118.51(10) . . ?
O2 N5 C15 117.98(10) . . ?
C91 O91 H91O 108.3 . . ?
O91 C91 H91A 109.5 . . ?
O91 C91 H91B 109.5 . . ?
H91A C91 H91B 109.5 . . ?
O91 C91 H91C 109.5 . . ?
H91A C91 H91C 109.5 . . ?
H91B C91 H91C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.948
_diffrn_reflns_theta_full        67.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.250
_refine_diff_density_min         -0.278
_refine_diff_density_rms         0.046

####################################################################### 
# 
# 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_con83a
_database_code_depnum_ccdc_archive 'CCDC 1062228'
_audit_update_record             
;
2015-04-28 deposited with the CCDC.
2015-09-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL
_chemical_name_systematic        
; 
3-[2-(4-nitrophenyl)ethenyl][1,2,4]triazolo[3,4-a]phthalazine
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H11 N5 O2'
_chemical_formula_sum            'C17 H11 N5 O2'
_chemical_formula_weight         317.31

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.9683(12)
_cell_length_b                   7.6250(17)
_cell_length_c                   14.408(3)
_cell_angle_alpha                75.576(14)
_cell_angle_beta                 87.07(2)
_cell_angle_gamma                68.757(17)
_cell_volume                     690.4(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    100.0(1)
_cell_measurement_reflns_used    1305
_cell_measurement_theta_min      2
_cell_measurement_theta_max      50

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.526
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             328
_exptl_absorpt_coefficient_mu    0.872
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2003)'
_exptl_absorpt_correction_T_min  0.870
_exptl_absorpt_correction_T_max  0.964
_exptl_special_details           ?

_diffrn_ambient_temperature      100.0(1)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         '30W microsource with MonoCap capillary'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEXII CCD area-detector'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 12.8
_diffrn_standards_number         8
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  19.67
_diffrn_standards_decay_%        0.00
_diffrn_reflns_number            7768
_diffrn_reflns_av_R_equivalents  0.0166
_diffrn_reflns_av_sigmaI/netI    0.0155
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.17
_diffrn_reflns_theta_max         84.08
_reflns_number_total             2625
_reflns_number_gt                2491
_reflns_threshold_expression     >2sigma(I)

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

_computing_data_collection       'APEX2 (Bruker, 2010)'
_computing_cell_refinement       'SAINT-Plus (Bruker, 2009)'
_computing_data_reduction        'SAINT-Plus (Bruker, 2009)'
_computing_structure_solution    'SHELXS (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2008)'
_computing_molecular_graphics    
;XP in SHELXTL/PC (Sheldrick, 2008)
 ORTEP-3 W v. 1.062 (Farrugia 2012)
;
_computing_publication_material  
;SHELXL (Sheldrick, 2008) and
 PLATON (Spek, 2009)
;

_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)+(0.0583P)²+0.2448P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2625
_refine_ls_number_parameters     217
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0362
_refine_ls_R_factor_gt           0.0348
_refine_ls_wR_factor_ref         0.0991
_refine_ls_wR_factor_gt          0.0959
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_refine_ls_shift/su_max          0.001
_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 0.80089(17) -0.49838(16) 0.92413(8) 0.0161(2) Uani 1 1 d . . .
N1 N 0.76919(14) -0.30282(14) 0.90365(7) 0.0160(2) Uani 1 1 d . . .
N2 N 0.70073(15) -0.18249(14) 0.96541(7) 0.0188(2) Uani 1 1 d . . .
C2 C 0.66421(18) -0.27153(17) 1.05261(8) 0.0188(3) Uani 1 1 d . . .
H2 H 0.6168 -0.1940 1.0974 0.023 Uiso 1 1 calc R . .
C3 C 0.68943(17) -0.47566(17) 1.08647(8) 0.0180(3) Uani 1 1 d . . .
C4 C 0.76061(17) -0.59459(16) 1.02138(8) 0.0166(3) Uani 1 1 d . . .
C5 C 0.64281(18) -0.55663(18) 1.18260(8) 0.0212(3) Uani 1 1 d . . .
H5 H 0.5932 -0.4757 1.2258 0.025 Uiso 1 1 calc R . .
C6 C 0.66998(19) -0.75260(19) 1.21249(8) 0.0231(3) Uani 1 1 d . . .
H6 H 0.6396 -0.8063 1.2759 0.028 Uiso 1 1 calc R . .
C7 C 0.74313(19) -0.86996(18) 1.14739(9) 0.0230(3) Uani 1 1 d . . .
H7 H 0.7640 -1.0042 1.1678 0.028 Uiso 1 1 calc R . .
C8 C 0.78650(18) -0.79275(17) 1.05201(9) 0.0198(3) Uani 1 1 d . . .
H8 H 0.8328 -0.8742 1.0089 0.024 Uiso 1 1 calc R . .
N3 N 0.86400(15) -0.56202(14) 0.84569(7) 0.0188(2) Uani 1 1 d . . .
N4 N 0.87259(15) -0.40371(14) 0.77199(7) 0.0194(2) Uani 1 1 d . . .
C9 C 0.81463(17) -0.24927(17) 0.80728(8) 0.0175(3) Uani 1 1 d . . .
C10 C 0.79703(18) -0.05198(17) 0.75510(8) 0.0191(3) Uani 1 1 d . . .
H10 H 0.7754 0.0433 0.7902 0.023 Uiso 1 1 calc R . .
C11 C 0.81039(18) -0.00129(17) 0.65944(9) 0.0198(3) Uani 1 1 d . . .
H11 H 0.8345 -0.1016 0.6274 0.024 Uiso 1 1 calc R . .
C12 C 0.79227(17) 0.19158(17) 0.59777(8) 0.0180(3) Uani 1 1 d . . .
C13 C 0.77506(18) 0.35100(17) 0.63291(8) 0.0189(3) Uani 1 1 d . . .
H13 H 0.7826 0.3363 0.7002 0.023 Uiso 1 1 calc R . .
C14 C 0.74700(18) 0.53183(17) 0.57081(9) 0.0199(3) Uani 1 1 d . . .
H14 H 0.7316 0.6403 0.5956 0.024 Uiso 1 1 calc R . .
C15 C 0.74179(17) 0.55141(16) 0.47284(8) 0.0178(3) Uani 1 1 d . . .
C16 C 0.76823(18) 0.39598(17) 0.43527(8) 0.0193(3) Uani 1 1 d . . .
H16 H 0.7715 0.4095 0.3679 0.023 Uiso 1 1 calc R . .
C17 C 0.79030(19) 0.21716(17) 0.49854(8) 0.0201(3) Uani 1 1 d . . .
H17 H 0.8044 0.1098 0.4731 0.024 Uiso 1 1 calc R . .
N5 N 0.70868(16) 0.74274(14) 0.40600(7) 0.0214(2) Uani 1 1 d . . .
O1 O 0.68580(17) 0.88103(13) 0.43922(7) 0.0334(3) Uani 1 1 d . . .
O2 O 0.70242(15) 0.75618(13) 0.32015(6) 0.0286(2) Uani 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
C1 N3 1.3318(15) . ?
C1 N1 1.3814(15) . ?
C1 C4 1.4755(16) . ?
N1 N2 1.3811(14) . ?
N1 C9 1.4006(15) . ?
N2 C2 1.3311(16) . ?
C2 C3 1.4573(17) . ?
C2 H2 0.9500 . ?
C3 C4 1.4135(17) . ?
C3 C5 1.4417(17) . ?
C4 C8 1.4103(17) . ?
C5 C6 1.3917(18) . ?
C5 H5 0.9500 . ?
C6 C7 1.4069(18) . ?
C6 H6 0.9500 . ?
C7 C8 1.4177(18) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
N3 N4 1.4126(14) . ?
N4 C9 1.3195(15) . ?
C9 C10 1.4681(17) . ?
C10 C11 1.3437(17) . ?
C10 H10 0.9500 . ?
C11 C12 1.4813(16) . ?
C11 H11 0.9500 . ?
C12 C13 1.3939(16) . ?
C12 C17 1.3942(16) . ?
C13 C14 1.3957(17) . ?
C13 H13 0.9500 . ?
C14 C15 1.3830(17) . ?
C14 H14 0.9500 . ?
C15 C16 1.3721(17) . ?
C15 N5 1.4792(15) . ?
C16 C17 1.3990(17) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
N5 O2 1.2171(14) . ?
N5 O1 1.2199(14) . ?

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
N3 C1 N1 108.67(10) . . ?
N3 C1 C4 132.74(11) . . ?
N1 C1 C4 118.59(10) . . ?
N2 N1 C1 126.70(10) . . ?
N2 N1 C9 126.70(10) . . ?
C1 N1 C9 106.58(9) . . ?
C2 N2 N1 113.86(10) . . ?
N2 C2 C3 126.75(11) . . ?
N2 C2 H2 116.6 . . ?
C3 C2 H2 116.6 . . ?
C4 C3 C5 120.11(11) . . ?
C4 C3 C2 117.81(11) . . ?
C5 C3 C2 122.08(11) . . ?
C8 C4 C3 119.14(11) . . ?
C8 C4 C1 124.56(11) . . ?
C3 C4 C1 116.29(11) . . ?
C6 C5 C3 120.41(11) . . ?
C6 C5 H5 119.8 . . ?
C3 C5 H5 119.8 . . ?
C5 C6 C7 118.94(11) . . ?
C5 C6 H6 120.5 . . ?
C7 C6 H6 120.5 . . ?
C6 C7 C8 121.62(11) . . ?
C6 C7 H7 119.2 . . ?
C8 C7 H7 119.2 . . ?
C4 C8 C7 119.76(11) . . ?
C4 C8 H8 120.1 . . ?
C7 C8 H8 120.1 . . ?
C1 N3 N4 108.07(9) . . ?
C9 N4 N3 107.85(10) . . ?
N4 C9 N1 108.83(10) . . ?
N4 C9 C10 126.37(11) . . ?
N1 C9 C10 124.80(10) . . ?
C11 C10 C9 122.36(11) . . ?
C11 C10 H10 118.8 . . ?
C9 C10 H10 118.8 . . ?
C10 C11 C12 128.08(11) . . ?
C10 C11 H11 116.0 . . ?
C12 C11 H11 116.0 . . ?
C13 C12 C17 117.58(11) . . ?
C13 C12 C11 123.91(11) . . ?
C17 C12 C11 118.51(11) . . ?
C12 C13 C14 121.07(11) . . ?
C12 C13 H13 119.5 . . ?
C14 C13 H13 119.5 . . ?
C15 C14 C13 119.31(11) . . ?
C15 C14 H14 120.3 . . ?
C13 C14 H14 120.3 . . ?
C16 C15 C14 121.46(11) . . ?
C16 C15 N5 118.51(11) . . ?
C14 C15 N5 120.03(11) . . ?
C15 C16 C17 118.39(11) . . ?
C15 C16 H16 120.8 . . ?
C17 C16 H16 120.8 . . ?
C12 C17 C16 122.08(11) . . ?
C12 C17 H17 119.0 . . ?
C16 C17 H17 119.0 . . ?
O2 N5 O1 122.75(10) . . ?
O2 N5 C15 118.60(10) . . ?
O1 N5 C15 118.64(10) . . ?

_diffrn_measured_fraction_theta_max 0.848
_diffrn_reflns_theta_full        67.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.273
_refine_diff_density_min         -0.294
_refine_diff_density_rms         0.053

####################################################################### 
# 
# 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_con84
_database_code_depnum_ccdc_archive 'CCDC 1062229'
_audit_update_record             
;
2015-04-28 deposited with the CCDC.
2015-09-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL
_chemical_name_systematic        
'2-(3-phenylprop-2-en-1-ylidene)-1-(phthalazin-1(2H)-ylidene)hydrazinium chloride methanol solvate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H15 N4 +, C H4 O, Cl -'
_chemical_formula_sum            'C18 H19 Cl N4 O'
_chemical_formula_weight         342.82

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P b c a'
_symmetry_space_group_name_Hall  '-P 2ac 2ab'

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

_cell_length_a                   12.3783(8)
_cell_length_b                   13.7779(9)
_cell_length_c                   19.8004(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3376.9(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    100.0(1)
_cell_measurement_reflns_used    1044
_cell_measurement_theta_min      2
_cell_measurement_theta_max      50

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.207
_exptl_crystal_size_mid          0.205
_exptl_crystal_size_min          0.189
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.349
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1440
_exptl_absorpt_coefficient_mu    2.101
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2003)'
_exptl_absorpt_correction_T_min  0.668
_exptl_absorpt_correction_T_max  0.675
_exptl_special_details           ?

_diffrn_ambient_temperature      100.0(1)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         '30W microsource with MonoCap capillary'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEXII CCD area-detector'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 12.8
_diffrn_standards_number         10
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  17.33
_diffrn_standards_decay_%        0.00
_diffrn_reflns_number            34618
_diffrn_reflns_av_R_equivalents  0.0231
_diffrn_reflns_av_sigmaI/netI    0.0123
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         4.47
_diffrn_reflns_theta_max         72.45
_reflns_number_total             3260
_reflns_number_gt                3256
_reflns_threshold_expression     >2sigma(I)

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

_computing_data_collection       'APEX2 (Bruker, 2010)'
_computing_cell_refinement       'SAINT-Plus (Bruker, 2009)'
_computing_data_reduction        'SAINT-Plus (Bruker, 2009)'
_computing_structure_solution    'SHELXS (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2008)'
_computing_molecular_graphics    
;XP in SHELXTL/PC (Sheldrick, 2008)
 ORTEP-3 W v. 1.062 (Farrugia 2012)
;
_computing_publication_material  
;SHELXL (Sheldrick, 2008) and
 PLATON (Spek, 2009)
;

_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     
'w=1/[σ²(Fo²)+(0.0447P)²+1.5642P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0046(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3260
_refine_ls_number_parameters     219
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0307
_refine_ls_R_factor_gt           0.0307
_refine_ls_wR_factor_ref         0.0820
_refine_ls_wR_factor_gt          0.0819
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_restrained_S_all      1.075
_refine_ls_shift/su_max          0.001
_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 0.36703(9) 0.10584(8) 0.58371(5) 0.0117(2) Uani 1 1 d . . .
N1 N 0.43674(8) 0.08679(7) 0.63345(5) 0.0136(2) Uani 1 1 d . . .
H1N H 0.5154 0.0929 0.6252 0.016 Uiso 1 1 d R . .
N2 N 0.40959(8) 0.06539(8) 0.69903(5) 0.0174(2) Uani 1 1 d . . .
C2 C 0.30753(10) 0.06644(9) 0.71322(6) 0.0178(3) Uani 1 1 d . . .
H2 H 0.2870 0.0534 0.7586 0.021 Uiso 1 1 calc R . .
C3 C 0.22321(10) 0.08582(8) 0.66541(5) 0.0142(2) Uani 1 1 d . . .
C4 C 0.25293(9) 0.10341(8) 0.59769(5) 0.0122(2) Uani 1 1 d . . .
C5 C 0.11394(10) 0.08613(8) 0.68411(6) 0.0171(2) Uani 1 1 d . . .
H5 H 0.0938 0.0753 0.7298 0.021 Uiso 1 1 calc R . .
C6 C 0.03616(10) 0.10230(9) 0.63568(6) 0.0183(3) Uani 1 1 d . . .
H6 H -0.0379 0.1037 0.6482 0.022 Uiso 1 1 calc R . .
C7 C 0.06552(10) 0.11671(9) 0.56805(6) 0.0178(2) Uani 1 1 d . . .
H7 H 0.0108 0.1260 0.5350 0.021 Uiso 1 1 calc R . .
C8 C 0.17250(10) 0.11765(8) 0.54865(6) 0.0153(2) Uani 1 1 d . . .
H8 H 0.1916 0.1278 0.5027 0.018 Uiso 1 1 calc R . .
N3 N 0.40547(8) 0.12519(7) 0.52197(5) 0.0124(2) Uani 1 1 d . . .
H3N H 0.3663 0.1562 0.4907 0.015 Uiso 1 1 d R . .
N4 N 0.51603(8) 0.12255(7) 0.51273(5) 0.0138(2) Uani 1 1 d . . .
C9 C 0.54775(9) 0.13828(8) 0.45170(5) 0.0133(2) Uani 1 1 d . . .
H9 H 0.4963 0.1494 0.4169 0.016 Uiso 1 1 calc R . .
C10 C 0.66120(9) 0.13895(8) 0.43646(6) 0.0139(2) Uani 1 1 d . . .
H10 H 0.7115 0.1288 0.4720 0.017 Uiso 1 1 calc R . .
C11 C 0.69842(9) 0.15355(8) 0.37342(6) 0.0141(2) Uani 1 1 d . . .
H11 H 0.6458 0.1597 0.3387 0.017 Uiso 1 1 calc R . .
C12 C 0.81151(9) 0.16083(8) 0.35288(6) 0.0138(2) Uani 1 1 d . . .
C13 C 0.83675(10) 0.17769(9) 0.28495(6) 0.0183(3) Uani 1 1 d . . .
H13 H 0.7801 0.1821 0.2527 0.022 Uiso 1 1 calc R . .
C14 C 0.94282(10) 0.18800(10) 0.26391(6) 0.0235(3) Uani 1 1 d . . .
H14 H 0.9584 0.1993 0.2176 0.028 Uiso 1 1 calc R . .
C15 C 1.02619(10) 0.18186(10) 0.31046(7) 0.0236(3) Uani 1 1 d . . .
H15 H 1.0990 0.1892 0.2961 0.028 Uiso 1 1 calc R . .
C16 C 1.00304(10) 0.16500(9) 0.37806(6) 0.0208(3) Uani 1 1 d . . .
H16 H 1.0602 0.1608 0.4100 0.025 Uiso 1 1 calc R . .
C17 C 0.89688(10) 0.15430(9) 0.39925(6) 0.0167(2) Uani 1 1 d . . .
H17 H 0.8819 0.1424 0.4456 0.020 Uiso 1 1 calc R . .
Cl1 Cl 0.29797(2) 0.248665(19) 0.409152(14) 0.01809(11) Uani 1 1 d . . .
O91 O 0.15702(6) 0.41080(6) 0.35324(4) 0.01599(19) Uani 1 1 d . . .
H91O H 0.1921 0.3566 0.3705 0.024 Uiso 1 1 d R . .
C91 C 0.20472(11) 0.49423(9) 0.38337(7) 0.0246(3) Uani 1 1 d . . .
H91A H 0.1848 0.4971 0.4312 0.037 Uiso 1 1 calc R . .
H91B H 0.1787 0.5527 0.3604 0.037 Uiso 1 1 calc R . .
H91C H 0.2835 0.4903 0.3792 0.037 Uiso 1 1 calc R . .


_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 N1 1.3354(14) . ?
C1 N3 1.3386(14) . ?
C1 C4 1.4396(17) . ?
N1 N2 1.3734(13) . ?
N1 H1N 0.9914 . ?
N2 C2 1.2944(16) . ?
C2 C3 1.4342(16) . ?
C2 H2 0.9500 . ?
C3 C5 1.4023(17) . ?
C3 C4 1.4114(15) . ?
C4 C8 1.4045(16) . ?
C5 C6 1.3771(17) . ?
C5 H5 0.9500 . ?
C6 C7 1.4017(17) . ?
C6 H6 0.9500 . ?
C7 C8 1.3788(17) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
N3 N4 1.3813(14) . ?
N3 H3N 0.8948 . ?
N4 C9 1.2889(15) . ?
C9 C10 1.4365(16) . ?
C9 H9 0.9500 . ?
C10 C11 1.3456(16) . ?
C10 H10 0.9500 . ?
C11 C12 1.4613(16) . ?
C11 H11 0.9500 . ?
C12 C13 1.4002(16) . ?
C12 C17 1.4029(16) . ?
C13 C14 1.3848(17) . ?
C13 H13 0.9500 . ?
C14 C15 1.3862(18) . ?
C14 H14 0.9500 . ?
C15 C16 1.3884(18) . ?
C15 H15 0.9500 . ?
C16 C17 1.3873(18) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?
O91 C91 1.4234(15) . ?
O91 H91O 0.9289 . ?
C91 H91A 0.9800 . ?
C91 H91B 0.9800 . ?
C91 H91C 0.9800 . ?

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
N1 C1 N3 118.87(10) . . ?
N1 C1 C4 119.18(10) . . ?
N3 C1 C4 121.94(10) . . ?
C1 N1 N2 125.55(10) . . ?
C1 N1 H1N 119.7 . . ?
N2 N1 H1N 114.5 . . ?
C2 N2 N1 116.21(10) . . ?
N2 C2 C3 124.69(10) . . ?
N2 C2 H2 117.7 . . ?
C3 C2 H2 117.7 . . ?
C5 C3 C4 120.11(11) . . ?
C5 C3 C2 121.88(10) . . ?
C4 C3 C2 117.99(11) . . ?
C8 C4 C3 119.74(11) . . ?
C8 C4 C1 124.00(10) . . ?
C3 C4 C1 116.26(10) . . ?
C6 C5 C3 119.40(11) . . ?
C6 C5 H5 120.3 . . ?
C3 C5 H5 120.3 . . ?
C5 C6 C7 120.46(11) . . ?
C5 C6 H6 119.8 . . ?
C7 C6 H6 119.8 . . ?
C8 C7 C6 121.09(11) . . ?
C8 C7 H7 119.5 . . ?
C6 C7 H7 119.5 . . ?
C7 C8 C4 119.14(10) . . ?
C7 C8 H8 120.4 . . ?
C4 C8 H8 120.4 . . ?
C1 N3 N4 117.91(9) . . ?
C1 N3 H3N 122.3 . . ?
N4 N3 H3N 117.2 . . ?
C9 N4 N3 114.94(10) . . ?
N4 C9 C10 119.72(11) . . ?
N4 C9 H9 120.1 . . ?
C10 C9 H9 120.1 . . ?
C11 C10 C9 122.04(11) . . ?
C11 C10 H10 119.0 . . ?
C9 C10 H10 119.0 . . ?
C10 C11 C12 126.62(11) . . ?
C10 C11 H11 116.7 . . ?
C12 C11 H11 116.7 . . ?
C13 C12 C17 118.12(11) . . ?
C13 C12 C11 119.51(11) . . ?
C17 C12 C11 122.35(10) . . ?
C14 C13 C12 121.17(11) . . ?
C14 C13 H13 119.4 . . ?
C12 C13 H13 119.4 . . ?
C13 C14 C15 119.97(11) . . ?
C13 C14 H14 120.0 . . ?
C15 C14 H14 120.0 . . ?
C14 C15 C16 119.84(11) . . ?
C14 C15 H15 120.1 . . ?
C16 C15 H15 120.1 . . ?
C17 C16 C15 120.32(11) . . ?
C17 C16 H16 119.8 . . ?
C15 C16 H16 119.8 . . ?
C16 C17 C12 120.58(11) . . ?
C16 C17 H17 119.7 . . ?
C12 C17 H17 119.7 . . ?
C91 O91 H91O 107.5 . . ?
O91 C91 H91A 109.5 . . ?
O91 C91 H91B 109.5 . . ?
H91A C91 H91B 109.5 . . ?
O91 C91 H91C 109.5 . . ?
H91A C91 H91C 109.5 . . ?
H91B C91 H91C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.975
_diffrn_reflns_theta_full        67.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.238
_refine_diff_density_min         -0.362
_refine_diff_density_rms         0.056

####################################################################### 
# 
# 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_con84p
_database_code_depnum_ccdc_archive 'CCDC 1062230'
_audit_update_record             
;
2015-04-28 deposited with the CCDC.
2015-09-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL
_chemical_name_systematic        
; 
1-[(3-phenylprop-2-en-1-ylidene)hydrazinylidene]-1,2-dihydrophthalazine
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C17 H14 N4'
_chemical_formula_sum            'C17 H14 N4'
_chemical_formula_weight         274.32

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 '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/c'
_symmetry_space_group_name_Hall  '-P 2ybc'

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

_cell_length_a                   12.7373(9)
_cell_length_b                   4.8963(5)
_cell_length_c                   22.3300(16)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.249(9)
_cell_angle_gamma                90.00
_cell_volume                     1386.8(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100.0(1)
_cell_measurement_reflns_used    985
_cell_measurement_theta_min      2
_cell_measurement_theta_max      50

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.107
_exptl_crystal_size_mid          0.103
_exptl_crystal_size_min          0.048
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.314
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             576
_exptl_absorpt_coefficient_mu    0.643
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2003)'
_exptl_absorpt_correction_T_min  0.926
_exptl_absorpt_correction_T_max  0.975
_exptl_special_details           ?

_diffrn_ambient_temperature      100.0(1)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         '30W microsource with MonoCap capillary'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEXII CCD area-detector'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 12.8
_diffrn_standards_number         10
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  11.33
_diffrn_standards_decay_%        0.00
_diffrn_reflns_number            13311
_diffrn_reflns_av_R_equivalents  0.0196
_diffrn_reflns_av_sigmaI/netI    0.0132
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         3.48
_diffrn_reflns_theta_max         65.65
_reflns_number_total             2388
_reflns_number_gt                2258
_reflns_threshold_expression     >2sigma(I)

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

_computing_data_collection       'APEX2 (Bruker, 2010)'
_computing_cell_refinement       'SAINT-Plus (Bruker, 2009)'
_computing_data_reduction        'SAINT-Plus (Bruker, 2009)'
_computing_structure_solution    'SHELXS (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2008)'
_computing_molecular_graphics    
;XP in SHELXTL/PC (Sheldrick, 2008)
 ORTEP-3 W v. 1.062 (Farrugia 2012)
;
_computing_publication_material  
;SHELXL (Sheldrick, 2008) and
 PLATON (Spek, 2009)
;

_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     
'w=1/[σ²(Fo²)+(0.0491P)²+0.4066P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2388
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0329
_refine_ls_R_factor_gt           0.0315
_refine_ls_wR_factor_ref         0.0874
_refine_ls_wR_factor_gt          0.0860
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.059
_refine_ls_shift/su_max          0.001
_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 0.84170(8) 0.9859(2) 0.59242(4) 0.0163(2) Uani 1 1 d . . .
N1 N 0.92240(7) 0.99469(18) 0.55560(4) 0.0204(2) Uani 1 1 d . . .
H1N H 0.9189 0.8832 0.5215 0.025 Uiso 1 1 d R . .
N2 N 1.00507(7) 1.17281(19) 0.55945(4) 0.0229(2) Uani 1 1 d . . .
C2 C 1.01039(8) 1.3471(2) 0.60302(5) 0.0215(2) Uani 1 1 d . . .
H2 H 1.0672 1.4736 0.6060 0.026 Uiso 1 1 calc R . .
C3 C 0.93511(8) 1.3614(2) 0.64755(4) 0.0174(2) Uani 1 1 d . . .
C4 C 0.84993(8) 1.1784(2) 0.64254(4) 0.0163(2) Uani 1 1 d . . .
C5 C 0.94510(8) 1.5498(2) 0.69490(5) 0.0194(2) Uani 1 1 d . . .
H5 H 1.0029 1.6733 0.6986 0.023 Uiso 1 1 calc R . .
C6 C 0.87105(8) 1.5559(2) 0.73619(4) 0.0200(2) Uani 1 1 d . . .
H6 H 0.8776 1.6849 0.7681 0.024 Uiso 1 1 calc R . .
C7 C 0.78639(8) 1.3732(2) 0.73129(4) 0.0196(2) Uani 1 1 d . . .
H7 H 0.7356 1.3790 0.7599 0.024 Uiso 1 1 calc R . .
C8 C 0.77589(8) 1.1841(2) 0.68522(4) 0.0177(2) Uani 1 1 d . . .
H8 H 0.7188 1.0585 0.6825 0.021 Uiso 1 1 calc R . .
N3 N 0.76231(6) 0.81709(17) 0.58410(4) 0.0169(2) Uani 1 1 d . . .
N4 N 0.77538(7) 0.63986(18) 0.53623(4) 0.0188(2) Uani 1 1 d . . .
C9 C 0.69260(8) 0.4985(2) 0.52002(4) 0.0175(2) Uani 1 1 d . . .
H9 H 0.6301 0.5267 0.5393 0.021 Uiso 1 1 calc R . .
C10 C 0.69348(8) 0.2981(2) 0.47296(4) 0.0179(2) Uani 1 1 d . . .
H10 H 0.7579 0.2643 0.4559 0.021 Uiso 1 1 calc R . .
C11 C 0.60781(8) 0.1567(2) 0.45199(4) 0.0183(2) Uani 1 1 d . . .
H11 H 0.5444 0.1971 0.4696 0.022 Uiso 1 1 calc R . .
C12 C 0.60089(8) -0.0531(2) 0.40502(4) 0.0173(2) Uani 1 1 d . . .
C13 C 0.50247(8) -0.1648(2) 0.38575(5) 0.0210(2) Uani 1 1 d . . .
H13 H 0.4413 -0.1004 0.4027 0.025 Uiso 1 1 calc R . .
C14 C 0.49279(9) -0.3687(2) 0.34225(5) 0.0246(3) Uani 1 1 d . . .
H14 H 0.4255 -0.4447 0.3303 0.029 Uiso 1 1 calc R . .
C15 C 0.58082(9) -0.4613(2) 0.31632(5) 0.0235(3) Uani 1 1 d . . .
H15 H 0.5741 -0.5982 0.2861 0.028 Uiso 1 1 calc R . .
C16 C 0.67914(9) -0.3520(2) 0.33506(5) 0.0230(3) Uani 1 1 d . . .
H16 H 0.7398 -0.4155 0.3176 0.028 Uiso 1 1 calc R . .
C17 C 0.68953(8) -0.1519(2) 0.37889(5) 0.0202(2) Uani 1 1 d . . .
H17 H 0.7573 -0.0805 0.3914 0.024 Uiso 1 1 calc R . .


_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 N3 1.3060(13) . ?
C1 N1 1.3744(13) . ?
C1 C4 1.4597(14) . ?
N1 N2 1.3639(12) . ?
N1 H1N 0.9347 . ?
N2 C2 1.2914(14) . ?
C2 C3 1.4448(15) . ?
C2 H2 0.9500 . ?
C3 C5 1.4001(14) . ?
C3 C4 1.4035(15) . ?
C4 C8 1.4011(14) . ?
C5 C6 1.3784(15) . ?
C5 H5 0.9500 . ?
C6 C7 1.3979(15) . ?
C6 H6 0.9500 . ?
C7 C8 1.3814(14) . ?
C7 H7 0.9500 . ?
C8 H8 0.9500 . ?
N3 N4 1.3985(12) . ?
N4 C9 1.2853(14) . ?
C9 C10 1.4384(14) . ?
C9 H9 0.9500 . ?
C10 C11 1.3401(15) . ?
C10 H10 0.9500 . ?
C11 C12 1.4651(14) . ?
C11 H11 0.9500 . ?
C12 C13 1.3990(15) . ?
C12 C17 1.4033(15) . ?
C13 C14 1.3903(15) . ?
C13 H13 0.9500 . ?
C14 C15 1.3846(16) . ?
C14 H14 0.9500 . ?
C15 C16 1.3907(16) . ?
C15 H15 0.9500 . ?
C16 C17 1.3828(15) . ?
C16 H16 0.9500 . ?
C17 H17 0.9500 . ?

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
N3 C1 N1 123.12(9) . . ?
N3 C1 C4 121.21(9) . . ?
N1 C1 C4 115.66(9) . . ?
N2 N1 C1 126.71(9) . . ?
N2 N1 H1N 113.8 . . ?
C1 N1 H1N 119.1 . . ?
C2 N2 N1 117.20(9) . . ?
N2 C2 C3 123.92(10) . . ?
N2 C2 H2 118.0 . . ?
C3 C2 H2 118.0 . . ?
C5 C3 C4 119.80(9) . . ?
C5 C3 C2 122.09(9) . . ?
C4 C3 C2 118.11(9) . . ?
C8 C4 C3 119.78(9) . . ?
C8 C4 C1 121.91(9) . . ?
C3 C4 C1 118.31(9) . . ?
C6 C5 C3 119.94(10) . . ?
C6 C5 H5 120.0 . . ?
C3 C5 H5 120.0 . . ?
C5 C6 C7 120.25(10) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 H6 119.9 . . ?
C8 C7 C6 120.59(9) . . ?
C8 C7 H7 119.7 . . ?
C6 C7 H7 119.7 . . ?
C7 C8 C4 119.63(9) . . ?
C7 C8 H8 120.2 . . ?
C4 C8 H8 120.2 . . ?
C1 N3 N4 110.90(8) . . ?
C9 N4 N3 113.43(8) . . ?
N4 C9 C10 120.81(9) . . ?
N4 C9 H9 119.6 . . ?
C10 C9 H9 119.6 . . ?
C11 C10 C9 123.17(9) . . ?
C11 C10 H10 118.4 . . ?
C9 C10 H10 118.4 . . ?
C10 C11 C12 127.31(9) . . ?
C10 C11 H11 116.3 . . ?
C12 C11 H11 116.3 . . ?
C13 C12 C17 118.02(10) . . ?
C13 C12 C11 119.20(9) . . ?
C17 C12 C11 122.77(9) . . ?
C14 C13 C12 121.02(10) . . ?
C14 C13 H13 119.5 . . ?
C12 C13 H13 119.5 . . ?
C15 C14 C13 120.26(10) . . ?
C15 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C14 C15 C16 119.31(10) . . ?
C14 C15 H15 120.3 . . ?
C16 C15 H15 120.3 . . ?
C17 C16 C15 120.72(10) . . ?
C17 C16 H16 119.6 . . ?
C15 C16 H16 119.6 . . ?
C16 C17 C12 120.66(10) . . ?
C16 C17 H17 119.7 . . ?
C12 C17 H17 119.7 . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        65.65
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.147
_refine_diff_density_min         -0.235
_refine_diff_density_rms         0.040

