# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2019

####################################################################### 
# 
# 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_P2AJK
_database_code_depnum_ccdc_archive 'CCDC 1878538'
loop_
_audit_author_name
_audit_author_address
'Muhammad Nawaz Tahir' 'University of Sargodha'
_audit_update_record             
;
2019-03-29 deposited with the CCDC.	2019-04-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_absolute_configuration .
_chemical_name_systematic        
;
N'-[(3Z)-2-oxo-1-propyl-1,2-dihydro-3H-indol-3-ylidene]furan-2-carbohydrazide
;
_chemical_formula_moiety         'C18 H17 N3 O2'
_chemical_formula_sum            'C18 H17 N3 O2'
_chemical_formula_iupac          'C18 H17 N3 O2'
_chemical_formula_weight         307.34

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   7.167(2)
_cell_length_b                   24.911(9)
_cell_length_c                   8.898(3)
_cell_angle_alpha                90
_cell_angle_beta                 94.712(14)
_cell_angle_gamma                90
_cell_volume                     1583.3(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1636
_cell_measurement_theta_min      2.438
_cell_measurement_theta_max      26.000
_cell_measurement_temperature    296(2)
_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.22
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             648
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_absorpt_correction_T_min  0.945
_exptl_absorpt_correction_T_max  0.979
_exptl_special_details           
;
;


_diffrn_ambient_temperature      296(2)
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 0.78
_diffrn_reflns_number            9438
_diffrn_reflns_av_unetI/netI     0.0735
_diffrn_reflns_av_R_equivalents  0.0571
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -30
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.438
_diffrn_reflns_theta_max         26.000
_diffrn_reflns_theta_full        26.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?

_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 >
σ(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.
;
_reflns_number_total             3095
_reflns_number_gt                1636
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.1252
_refine_ls_R_factor_gt           0.0610
_refine_ls_wR_factor_ref         0.1796
_refine_ls_wR_factor_gt          0.1474
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.037
_refine_ls_number_reflns         3095
_refine_ls_number_parameters     208
_refine_ls_number_restraints     8
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0817P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/6  (Sheldrick, 2015)'
_computing_molecular_graphics    
'ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009)'
_computing_publication_material  
;
WinGX (Farrugia, 1999) and PLATON (Spek, 2009)
;

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.3420(3) -0.15183(8) 0.9647(2) 0.0723(6) Uani 1 1 d . . . . .
O2 O 0.2846(3) 0.03577(8) 0.7714(2) 0.0698(6) Uani 1 1 d . . . . .
N1 N 0.3133(3) -0.06587(8) 0.8821(2) 0.0530(6) Uani 1 1 d . . . . .
H1 H 0.3199 -0.0440 0.8079 0.064 Uiso 1 1 calc R U . . .
N2 N 0.2753(3) -0.04694(9) 1.0199(2) 0.0504(6) Uani 1 1 d . . . . .
N3 N 0.2074(3) 0.09248(9) 0.9624(3) 0.0624(7) Uani 1 1 d D . . . .
C1 C 0.3692(3) -0.13600(10) 0.7031(3) 0.0498(7) Uani 1 1 d . . . . .
C2 C 0.3705(4) -0.19004(12) 0.6721(4) 0.0773(10) Uani 1 1 d . . . . .
H2 H 0.3572 -0.2145 0.7495 0.093 Uiso 1 1 calc R U . . .
C3 C 0.3912(5) -0.20876(14) 0.5289(4) 0.0952(12) Uani 1 1 d . . . . .
H3 H 0.3930 -0.2455 0.5105 0.114 Uiso 1 1 calc R U . . .
C4 C 0.4091(4) -0.17338(14) 0.4138(4) 0.0806(10) Uani 1 1 d . . . . .
H4 H 0.4208 -0.1859 0.3166 0.097 Uiso 1 1 calc R U . . .
C5 C 0.4097(4) -0.11936(13) 0.4421(4) 0.0735(9) Uani 1 1 d . . . . .
H5 H 0.4235 -0.0952 0.3641 0.088 Uiso 1 1 calc R U . . .
C6 C 0.3901(4) -0.10063(12) 0.5859(3) 0.0627(8) Uani 1 1 d . . . . .
H6 H 0.3909 -0.0639 0.6042 0.075 Uiso 1 1 calc R U . . .
C7 C 0.3412(3) -0.11997(11) 0.8618(3) 0.0525(7) Uani 1 1 d . . . . .
C8 C 0.2439(3) 0.00398(11) 1.0262(3) 0.0453(6) Uani 1 1 d . . . . .
C9 C 0.1970(3) 0.03353(10) 1.1594(3) 0.0471(7) Uani 1 1 d . . . . .
C10 C 0.1740(4) 0.01892(12) 1.3057(3) 0.0624(8) Uani 1 1 d . . . . .
H10 H 0.1875 -0.0167 1.3360 0.075 Uiso 1 1 calc R U . . .
C11 C 0.1305(4) 0.05828(15) 1.4074(3) 0.0712(9) Uani 1 1 d . . . . .
H11 H 0.1151 0.0490 1.5069 0.085 Uiso 1 1 calc R U . . .
C12 C 0.1097(4) 0.11086(14) 1.3628(4) 0.0707(9) Uani 1 1 d . . . . .
H12 H 0.0807 0.1367 1.4326 0.085 Uiso 1 1 calc R U . . .
C13 C 0.1312(4) 0.12605(12) 1.2162(3) 0.0661(8) Uani 1 1 d . . . . .
H13 H 0.1160 0.1616 1.1859 0.079 Uiso 1 1 calc R U . . .
C14 C 0.1758(3) 0.08692(11) 1.1160(3) 0.0516(7) Uani 1 1 d . . . . .
C15 C 0.2481(4) 0.04419(11) 0.9028(3) 0.0526(7) Uani 1 1 d . . . . .
C16A C 0.2300(6) 0.14386(17) 0.8823(5) 0.0781(8) Uani 0.806(4) 1 d D . P A 1
H16A H 0.3163 0.1388 0.8051 0.094 Uiso 0.806(4) 1 calc R U P A 1
H16B H 0.2834 0.1704 0.9531 0.094 Uiso 0.806(4) 1 calc R U P A 1
C17A C 0.0480(5) 0.16412(16) 0.8111(5) 0.0781(8) Uani 0.806(4) 1 d D . P A 1
H17A H -0.0406 0.1675 0.8873 0.094 Uiso 0.806(4) 1 calc R U P A 1
H17B H -0.0024 0.1385 0.7363 0.094 Uiso 0.806(4) 1 calc R U P A 1
C18A C 0.0724(6) 0.21806(16) 0.7368(5) 0.0781(8) Uani 0.806(4) 1 d D . P A 1
H18A H 0.1042 0.2446 0.8128 0.117 Uiso 0.806(4) 1 calc R U P A 1
H18B H -0.0423 0.2280 0.6804 0.117 Uiso 0.806(4) 1 calc R U P A 1
H18C H 0.1707 0.2157 0.6701 0.117 Uiso 0.806(4) 1 calc R U P A 1
C16B C 0.088(2) 0.1350(6) 0.865(2) 0.0781(8) Uani 0.194(4) 1 d D . P A 2
H16C H 0.0594 0.1229 0.7617 0.094 Uiso 0.194(4) 1 calc R U P A 2
H16D H -0.0278 0.1439 0.9088 0.094 Uiso 0.194(4) 1 calc R U P A 2
C17B C 0.222(2) 0.1810(6) 0.873(2) 0.0781(8) Uani 0.194(4) 1 d D . P A 2
H17C H 0.3400 0.1680 0.8411 0.094 Uiso 0.194(4) 1 calc R U P A 2
H17D H 0.2445 0.1910 0.9787 0.094 Uiso 0.194(4) 1 calc R U P A 2
C18B C 0.171(3) 0.2309(6) 0.786(2) 0.0781(8) Uani 0.194(4) 1 d D . P A 2
H18D H 0.0493 0.2428 0.8084 0.117 Uiso 0.194(4) 1 calc R U P A 2
H18E H 0.1698 0.2234 0.6796 0.117 Uiso 0.194(4) 1 calc R U P A 2
H18F H 0.2615 0.2584 0.8122 0.117 Uiso 0.194(4) 1 calc R U P A 2


_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
O1 C7 1.211(3) . ?
O2 C15 1.236(3) . ?
N1 N2 1.362(3) . ?
N1 C7 1.377(3) . ?
N1 H1 0.8600 . ?
N2 C8 1.290(3) . ?
N3 C15 1.356(3) . ?
N3 C14 1.410(3) . ?
N3 C16A 1.480(4) . ?
N3 C16B 1.579(17) . ?
C1 C2 1.374(4) . ?
C1 C6 1.383(4) . ?
C1 C7 1.496(4) . ?
C2 C3 1.376(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.365(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.369(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.380(4) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C8 C9 1.457(3) . ?
C8 C15 1.489(4) . ?
C9 C10 1.375(3) . ?
C9 C14 1.390(4) . ?
C10 C11 1.387(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.373(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.379(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.376(4) . ?
C13 H13 0.9300 . ?
C16A C17A 1.491(5) . ?
C16A H16A 0.9700 . ?
C16A H16B 0.9700 . ?
C17A C18A 1.514(5) . ?
C17A H17A 0.9700 . ?
C17A H17B 0.9700 . ?
C18A H18A 0.9600 . ?
C18A H18B 0.9600 . ?
C18A H18C 0.9600 . ?
C16B C17B 1.494(16) . ?
C16B H16C 0.9700 . ?
C16B H16D 0.9700 . ?
C17B C18B 1.499(15) . ?
C17B H17C 0.9700 . ?
C17B H17D 0.9700 . ?
C18B H18D 0.9600 . ?
C18B H18E 0.9600 . ?
C18B H18F 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 N1 C7 120.0(2) . . ?
N2 N1 H1 120.0 . . ?
C7 N1 H1 120.0 . . ?
C8 N2 N1 115.4(2) . . ?
C15 N3 C14 110.4(2) . . ?
C15 N3 C16A 122.9(3) . . ?
C14 N3 C16A 125.7(3) . . ?
C15 N3 C16B 120.3(7) . . ?
C14 N3 C16B 118.5(7) . . ?
C2 C1 C6 118.0(3) . . ?
C2 C1 C7 117.0(3) . . ?
C6 C1 C7 124.9(2) . . ?
C1 C2 C3 121.4(3) . . ?
C1 C2 H2 119.3 . . ?
C3 C2 H2 119.3 . . ?
C4 C3 C2 120.0(3) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C4 C5 119.7(3) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C4 C5 C6 120.3(3) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C5 C6 C1 120.6(3) . . ?
C5 C6 H6 119.7 . . ?
C1 C6 H6 119.7 . . ?
O1 C7 N1 122.2(3) . . ?
O1 C7 C1 123.1(2) . . ?
N1 C7 C1 114.7(2) . . ?
N2 C8 C9 125.8(2) . . ?
N2 C8 C15 127.9(2) . . ?
C9 C8 C15 106.3(2) . . ?
C10 C9 C14 119.9(3) . . ?
C10 C9 C8 133.6(3) . . ?
C14 C9 C8 106.5(2) . . ?
C9 C10 C11 118.8(3) . . ?
C9 C10 H10 120.6 . . ?
C11 C10 H10 120.6 . . ?
C12 C11 C10 120.7(3) . . ?
C12 C11 H11 119.7 . . ?
C10 C11 H11 119.7 . . ?
C11 C12 C13 121.2(3) . . ?
C11 C12 H12 119.4 . . ?
C13 C12 H12 119.4 . . ?
C14 C13 C12 117.9(3) . . ?
C14 C13 H13 121.0 . . ?
C12 C13 H13 121.0 . . ?
C13 C14 C9 121.6(3) . . ?
C13 C14 N3 128.5(3) . . ?
C9 C14 N3 109.9(2) . . ?
O2 C15 N3 126.1(3) . . ?
O2 C15 C8 127.0(3) . . ?
N3 C15 C8 106.9(2) . . ?
N3 C16A C17A 111.8(3) . . ?
N3 C16A H16A 109.3 . . ?
C17A C16A H16A 109.3 . . ?
N3 C16A H16B 109.3 . . ?
C17A C16A H16B 109.3 . . ?
H16A C16A H16B 107.9 . . ?
C16A C17A C18A 111.0(4) . . ?
C16A C17A H17A 109.4 . . ?
C18A C17A H17A 109.4 . . ?
C16A C17A H17B 109.4 . . ?
C18A C17A H17B 109.4 . . ?
H17A C17A H17B 108.0 . . ?
C17A C18A H18A 109.5 . . ?
C17A C18A H18B 109.5 . . ?
H18A C18A H18B 109.5 . . ?
C17A C18A H18C 109.5 . . ?
H18A C18A H18C 109.5 . . ?
H18B C18A H18C 109.5 . . ?
C17B C16B N3 99.6(12) . . ?
C17B C16B H16C 111.9 . . ?
N3 C16B H16C 111.9 . . ?
C17B C16B H16D 111.9 . . ?
N3 C16B H16D 111.9 . . ?
H16C C16B H16D 109.6 . . ?
C16B C17B C18B 118.7(14) . . ?
C16B C17B H17C 107.6 . . ?
C18B C17B H17C 107.6 . . ?
C16B C17B H17D 107.6 . . ?
C18B C17B H17D 107.6 . . ?
H17C C17B H17D 107.1 . . ?
C17B C18B H18D 109.5 . . ?
C17B C18B H18E 109.5 . . ?
H18D C18B H18E 109.5 . . ?
C17B C18B H18F 109.5 . . ?
H18D C18B H18F 109.5 . . ?
H18E C18B H18F 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 N1 N2 C8 -177.3(2) . . . . ?
C6 C1 C2 C3 -0.3(4) . . . . ?
C7 C1 C2 C3 178.6(3) . . . . ?
C1 C2 C3 C4 -0.6(5) . . . . ?
C2 C3 C4 C5 1.2(5) . . . . ?
C3 C4 C5 C6 -0.8(5) . . . . ?
C4 C5 C6 C1 -0.1(4) . . . . ?
C2 C1 C6 C5 0.6(4) . . . . ?
C7 C1 C6 C5 -178.1(2) . . . . ?
N2 N1 C7 O1 -3.6(4) . . . . ?
N2 N1 C7 C1 176.12(19) . . . . ?
C2 C1 C7 O1 8.8(4) . . . . ?
C6 C1 C7 O1 -172.4(3) . . . . ?
C2 C1 C7 N1 -170.8(2) . . . . ?
C6 C1 C7 N1 7.9(3) . . . . ?
N1 N2 C8 C9 178.8(2) . . . . ?
N1 N2 C8 C15 -1.3(4) . . . . ?
N2 C8 C9 C10 0.3(4) . . . . ?
C15 C8 C9 C10 -179.5(3) . . . . ?
N2 C8 C9 C14 179.8(2) . . . . ?
C15 C8 C9 C14 -0.1(2) . . . . ?
C14 C9 C10 C11 -0.2(4) . . . . ?
C8 C9 C10 C11 179.2(3) . . . . ?
C9 C10 C11 C12 0.3(4) . . . . ?
C10 C11 C12 C13 0.1(5) . . . . ?
C11 C12 C13 C14 -0.6(4) . . . . ?
C12 C13 C14 C9 0.7(4) . . . . ?
C12 C13 C14 N3 -179.0(3) . . . . ?
C10 C9 C14 C13 -0.3(4) . . . . ?
C8 C9 C14 C13 -179.9(2) . . . . ?
C10 C9 C14 N3 179.4(2) . . . . ?
C8 C9 C14 N3 -0.1(3) . . . . ?
C15 N3 C14 C13 180.0(3) . . . . ?
C16A N3 C14 C13 11.0(5) . . . . ?
C16B N3 C14 C13 -35.5(7) . . . . ?
C15 N3 C14 C9 0.3(3) . . . . ?
C16A N3 C14 C9 -168.7(3) . . . . ?
C16B N3 C14 C9 144.7(6) . . . . ?
C14 N3 C15 O2 -179.1(2) . . . . ?
C16A N3 C15 O2 -9.8(5) . . . . ?
C16B N3 C15 O2 37.1(8) . . . . ?
C14 N3 C15 C8 -0.3(3) . . . . ?
C16A N3 C15 C8 169.1(3) . . . . ?
C16B N3 C15 C8 -144.0(7) . . . . ?
N2 C8 C15 O2 -0.8(4) . . . . ?
C9 C8 C15 O2 179.1(2) . . . . ?
N2 C8 C15 N3 -179.6(2) . . . . ?
C9 C8 C15 N3 0.2(3) . . . . ?
C15 N3 C16A C17A 100.5(4) . . . . ?
C14 N3 C16A C17A -91.8(4) . . . . ?
N3 C16A C17A C18A 177.1(4) . . . . ?
C15 N3 C16B C17B -122.5(11) . . . . ?
C14 N3 C16B C17B 96.6(13) . . . . ?
N3 C16B C17B C18B 176.0(15) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O2 0.86 2.03 2.718(3) 136.8 .
C17A H17A O1 0.97 2.65 3.578(5) 160.3 3_557
C16B H16D O1 0.97 2.61 3.568(18) 171.1 3_557

_refine_diff_density_max         0.352
_refine_diff_density_min         -0.346
_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_P1AJK
_database_code_depnum_ccdc_archive 'CCDC 1878553'
loop_
_audit_author_name
_audit_author_address
'Muhammad Nawaz Tahir' 'University of Sargodha'
_audit_update_record             
;
2019-03-29 deposited with the CCDC.	2019-04-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_absolute_configuration .
_chemical_name_systematic        
;
3-Methyl-N'-[(3E)-2-oxo-1-propyl-1,2-dihydro-3H-indol-3-ylidene]benzohydrazide
;
_chemical_formula_moiety         'C19 H19 N3 O2'
_chemical_formula_sum            'C19 H19 N3 O2'
_chemical_formula_iupac          'C19 H19 N3 O2'
_chemical_formula_weight         321.37

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.7416(13)
_cell_length_b                   8.6214(17)
_cell_length_c                   13.993(2)
_cell_angle_alpha                98.324(5)
_cell_angle_beta                 104.603(8)
_cell_angle_gamma                107.114(7)
_cell_volume                     839.2(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2288
_cell_measurement_theta_min      2.828
_cell_measurement_theta_max      26.500
_cell_measurement_temperature    296(2)
_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.20
_exptl_crystal_density_diffrn    1.272
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             340
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_shelx_estimated_absorpt_T_min   0.969
_shelx_estimated_absorpt_T_max   0.983
_exptl_absorpt_correction_T_min  0.885
_exptl_absorpt_correction_T_max  0.965
_exptl_special_details           
;
;


_diffrn_ambient_temperature      296(2)
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 0.77
_diffrn_reflns_number            9518
_diffrn_reflns_av_unetI/netI     0.0563
_diffrn_reflns_av_R_equivalents  0.0473
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.828
_diffrn_reflns_theta_max         26.500
_diffrn_reflns_theta_full        26.500
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measured_fraction_theta_full 0.980
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?

_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 >
σ(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.
;
_reflns_number_total             3408
_reflns_number_gt                2288
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0774
_refine_ls_R_factor_gt           0.0473
_refine_ls_wR_factor_ref         0.1390
_refine_ls_wR_factor_gt          0.1184
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_restrained_S_all      1.027
_refine_ls_number_reflns         3408
_refine_ls_number_parameters     219
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0633P)²+0.0561P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/6  (Sheldrick, 2015)'
_computing_molecular_graphics    
'ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009)'
_computing_publication_material  
;
WinGX (Farrugia, 1999) and PLATON (Spek, 2009)
;

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.1881(2) 0.19859(18) 0.35596(11) 0.0852(5) Uani 1 1 d . . . . .
O2 O 0.32723(18) 0.36924(14) 0.05092(10) 0.0600(4) Uani 1 1 d . . . . .
N1 N 0.2509(2) 0.26660(17) 0.21507(11) 0.0547(4) Uani 1 1 d . . . . .
H1 H 0.2840 0.3454 0.1850 0.066 Uiso 1 1 calc R U . . .
N2 N 0.22467(19) 0.10776(17) 0.16959(11) 0.0496(4) Uani 1 1 d . . . . .
N3 N 0.30677(19) 0.14062(16) -0.06613(11) 0.0476(4) Uani 1 1 d . . . . .
C1 C 0.2488(2) 0.4831(2) 0.34503(13) 0.0531(5) Uani 1 1 d . . . . .
C2 C 0.2599(3) 0.5360(3) 0.44570(15) 0.0653(5) Uani 1 1 d . . . . .
H2 H 0.2545 0.4602 0.4869 0.078 Uiso 1 1 calc R U . . .
C3 C 0.2788(3) 0.6992(3) 0.48647(15) 0.0672(6) Uani 1 1 d . . . . .
C4 C 0.2882(3) 0.8098(3) 0.42395(16) 0.0673(6) Uani 1 1 d . . . . .
H4 H 0.3018 0.9198 0.4499 0.081 Uiso 1 1 calc R U . . .
C5 C 0.2778(3) 0.7602(2) 0.32419(15) 0.0649(5) Uani 1 1 d . . . . .
H5 H 0.2838 0.8364 0.2833 0.078 Uiso 1 1 calc R U . . .
C6 C 0.2584(3) 0.5975(2) 0.28447(15) 0.0587(5) Uani 1 1 d . . . . .
H6 H 0.2517 0.5645 0.2170 0.070 Uiso 1 1 calc R U . . .
C7 C 0.2891(4) 0.7539(3) 0.59578(17) 0.1015(9) Uani 1 1 d . . . . .
H7A H 0.2631 0.6582 0.6245 0.152 Uiso 1 1 calc R U . . .
H7B H 0.1966 0.8066 0.5988 0.152 Uiso 1 1 calc R U . . .
H7C H 0.4140 0.8316 0.6335 0.152 Uiso 1 1 calc R U . . .
C8 C 0.2256(3) 0.3042(2) 0.30857(14) 0.0581(5) Uani 1 1 d . . . . .
C9 C 0.2457(2) 0.08741(19) 0.08033(13) 0.0427(4) Uani 1 1 d . . . . .
C10 C 0.2260(2) -0.06912(19) 0.01599(12) 0.0420(4) Uani 1 1 d . . . . .
C11 C 0.1805(2) -0.2316(2) 0.02661(14) 0.0511(4) Uani 1 1 d . . . . .
H11 H 0.1521 -0.2582 0.0843 0.061 Uiso 1 1 calc R U . . .
C12 C 0.1778(3) -0.3541(2) -0.04993(15) 0.0603(5) Uani 1 1 d . . . . .
H12 H 0.1485 -0.4640 -0.0435 0.072 Uiso 1 1 calc R U . . .
C13 C 0.2184(3) -0.3144(2) -0.13594(15) 0.0605(5) Uani 1 1 d . . . . .
H13 H 0.2165 -0.3984 -0.1865 0.073 Uiso 1 1 calc R U . . .
C14 C 0.2617(2) -0.1531(2) -0.14864(14) 0.0541(5) Uani 1 1 d . . . . .
H14 H 0.2879 -0.1271 -0.2069 0.065 Uiso 1 1 calc R U . . .
C15 C 0.2644(2) -0.03192(19) -0.07150(13) 0.0436(4) Uani 1 1 d . . . . .
C16 C 0.2978(2) 0.2191(2) 0.02309(13) 0.0466(4) Uani 1 1 d . . . . .
C17 C 0.3529(2) 0.2230(2) -0.14538(13) 0.0522(4) Uani 1 1 d . . . . .
H17A H 0.4321 0.1741 -0.1740 0.063 Uiso 1 1 calc R U . . .
H17B H 0.4257 0.3403 -0.1150 0.063 Uiso 1 1 calc R U . . .
C18 C 0.1797(3) 0.2082(2) -0.22943(14) 0.0630(5) Uani 1 1 d . . . . .
H18A H 0.1083 0.2692 -0.2027 0.076 Uiso 1 1 calc R U . . .
H18B H 0.0988 0.0918 -0.2547 0.076 Uiso 1 1 calc R U . . .
C19 C 0.2312(3) 0.2759(3) -0.31660(17) 0.0852(7) Uani 1 1 d . . . . .
H19A H 0.3168 0.3893 -0.2913 0.128 Uiso 1 1 calc R U . . .
H19B H 0.1179 0.2720 -0.3662 0.128 Uiso 1 1 calc R U . . .
H19C H 0.2913 0.2092 -0.3474 0.128 Uiso 1 1 calc R U . . .


_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
O1 C8 1.212(2) . ?
O2 C16 1.2309(18) . ?
N1 N2 1.3566(18) . ?
N1 C8 1.378(2) . ?
N1 H1 0.8600 . ?
N2 C9 1.293(2) . ?
N3 C16 1.359(2) . ?
N3 C15 1.4121(19) . ?
N3 C17 1.463(2) . ?
C1 C6 1.388(3) . ?
C1 C2 1.389(3) . ?
C1 C8 1.495(3) . ?
C2 C3 1.390(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.383(3) . ?
C3 C7 1.509(3) . ?
C4 C5 1.374(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.381(2) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C9 C10 1.454(2) . ?
C9 C16 1.500(2) . ?
C10 C11 1.380(2) . ?
C10 C15 1.390(2) . ?
C11 C12 1.383(2) . ?
C11 H11 0.9300 . ?
C12 C13 1.382(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.381(2) . ?
C13 H13 0.9300 . ?
C14 C15 1.380(2) . ?
C14 H14 0.9300 . ?
C17 C18 1.503(2) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 C19 1.517(3) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 N1 C8 121.29(15) . . ?
N2 N1 H1 119.4 . . ?
C8 N1 H1 119.4 . . ?
C9 N2 N1 115.50(14) . . ?
C16 N3 C15 110.25(13) . . ?
C16 N3 C17 124.88(13) . . ?
C15 N3 C17 124.87(14) . . ?
C6 C1 C2 118.69(18) . . ?
C6 C1 C8 124.06(17) . . ?
C2 C1 C8 117.25(18) . . ?
C1 C2 C3 121.7(2) . . ?
C1 C2 H2 119.2 . . ?
C3 C2 H2 119.2 . . ?
C4 C3 C2 118.05(18) . . ?
C4 C3 C7 121.1(2) . . ?
C2 C3 C7 120.9(2) . . ?
C5 C4 C3 121.24(19) . . ?
C5 C4 H4 119.4 . . ?
C3 C4 H4 119.4 . . ?
C4 C5 C6 120.2(2) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C5 C6 C1 120.19(18) . . ?
C5 C6 H6 119.9 . . ?
C1 C6 H6 119.9 . . ?
C3 C7 H7A 109.5 . . ?
C3 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C3 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O1 C8 N1 121.59(18) . . ?
O1 C8 C1 123.94(17) . . ?
N1 C8 C1 114.47(16) . . ?
N2 C9 C10 126.38(15) . . ?
N2 C9 C16 127.40(15) . . ?
C10 C9 C16 106.22(14) . . ?
C11 C10 C15 119.87(15) . . ?
C11 C10 C9 133.45(16) . . ?
C15 C10 C9 106.67(14) . . ?
C10 C11 C12 118.87(17) . . ?
C10 C11 H11 120.6 . . ?
C12 C11 H11 120.6 . . ?
C13 C12 C11 120.43(17) . . ?
C13 C12 H12 119.8 . . ?
C11 C12 H12 119.8 . . ?
C14 C13 C12 121.58(17) . . ?
C14 C13 H13 119.2 . . ?
C12 C13 H13 119.2 . . ?
C15 C14 C13 117.37(17) . . ?
C15 C14 H14 121.3 . . ?
C13 C14 H14 121.3 . . ?
C14 C15 C10 121.87(15) . . ?
C14 C15 N3 127.94(15) . . ?
C10 C15 N3 110.19(14) . . ?
O2 C16 N3 126.28(15) . . ?
O2 C16 C9 127.04(16) . . ?
N3 C16 C9 106.68(13) . . ?
N3 C17 C18 113.06(14) . . ?
N3 C17 H17A 109.0 . . ?
C18 C17 H17A 109.0 . . ?
N3 C17 H17B 109.0 . . ?
C18 C17 H17B 109.0 . . ?
H17A C17 H17B 107.8 . . ?
C17 C18 C19 112.01(16) . . ?
C17 C18 H18A 109.2 . . ?
C19 C18 H18A 109.2 . . ?
C17 C18 H18B 109.2 . . ?
C19 C18 H18B 109.2 . . ?
H18A C18 H18B 107.9 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C8 N1 N2 C9 177.48(15) . . . . ?
C6 C1 C2 C3 0.5(3) . . . . ?
C8 C1 C2 C3 -179.09(17) . . . . ?
C1 C2 C3 C4 -0.6(3) . . . . ?
C1 C2 C3 C7 179.50(19) . . . . ?
C2 C3 C4 C5 0.5(3) . . . . ?
C7 C3 C4 C5 -179.6(2) . . . . ?
C3 C4 C5 C6 -0.3(3) . . . . ?
C4 C5 C6 C1 0.2(3) . . . . ?
C2 C1 C6 C5 -0.3(3) . . . . ?
C8 C1 C6 C5 179.26(17) . . . . ?
N2 N1 C8 O1 3.7(3) . . . . ?
N2 N1 C8 C1 -176.52(14) . . . . ?
C6 C1 C8 O1 -168.18(19) . . . . ?
C2 C1 C8 O1 11.3(3) . . . . ?
C6 C1 C8 N1 12.0(3) . . . . ?
C2 C1 C8 N1 -168.48(16) . . . . ?
N1 N2 C9 C10 179.83(14) . . . . ?
N1 N2 C9 C16 0.9(2) . . . . ?
N2 C9 C10 C11 1.0(3) . . . . ?
C16 C9 C10 C11 -179.85(16) . . . . ?
N2 C9 C10 C15 -178.86(15) . . . . ?
C16 C9 C10 C15 0.27(17) . . . . ?
C15 C10 C11 C12 1.3(2) . . . . ?
C9 C10 C11 C12 -178.61(17) . . . . ?
C10 C11 C12 C13 -0.6(3) . . . . ?
C11 C12 C13 C14 -0.3(3) . . . . ?
C12 C13 C14 C15 0.5(3) . . . . ?
C13 C14 C15 C10 0.2(2) . . . . ?
C13 C14 C15 N3 179.08(15) . . . . ?
C11 C10 C15 C14 -1.1(2) . . . . ?
C9 C10 C15 C14 178.81(14) . . . . ?
C11 C10 C15 N3 179.84(13) . . . . ?
C9 C10 C15 N3 -0.25(17) . . . . ?
C16 N3 C15 C14 -178.85(16) . . . . ?
C17 N3 C15 C14 1.4(3) . . . . ?
C16 N3 C15 C10 0.14(18) . . . . ?
C17 N3 C15 C10 -179.62(14) . . . . ?
C15 N3 C16 O2 179.96(15) . . . . ?
C17 N3 C16 O2 -0.3(3) . . . . ?
C15 N3 C16 C9 0.03(17) . . . . ?
C17 N3 C16 C9 179.80(14) . . . . ?
N2 C9 C16 O2 -1.0(3) . . . . ?
C10 C9 C16 O2 179.89(15) . . . . ?
N2 C9 C16 N3 178.92(15) . . . . ?
C10 C9 C16 N3 -0.18(17) . . . . ?
C16 N3 C17 C18 -97.45(19) . . . . ?
C15 N3 C17 C18 82.3(2) . . . . ?
N3 C17 C18 C19 -173.06(17) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O2 0.86 2.01 2.7154(19) 138.0 .
C17 H17B O2 0.97 2.53 3.482(2) 166.9 2_665

_refine_diff_density_max         0.150
_refine_diff_density_min         -0.151
_refine_diff_density_rms         0.032

####################################################################### 
# 
# 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_P3AJK
_database_code_depnum_ccdc_archive 'CCDC 1878545'
loop_
_audit_author_name
_audit_author_address
'Muhammad Nawaz Tahir' 'University of Sargodha'
_audit_update_record             
;
2019-03-29 deposited with the CCDC.	2019-04-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_absolute_configuration .
_chemical_name_systematic        
;
N'-[(3Z)-2-oxo-1-propyl-1,2-dihydro-3H-indol-3-ylidene]-2-phenylacetohydrazide
;
_chemical_formula_moiety         'C19 H19 N3 O2'
_chemical_formula_sum            'C19 H19 N3 O2'
_chemical_formula_iupac          'C19 H19 N3 O2'
_chemical_formula_weight         321.37

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   14.4085(13)
_cell_length_b                   7.0847(5)
_cell_length_c                   17.8231(14)
_cell_angle_alpha                90
_cell_angle_beta                 111.465(5)
_cell_angle_gamma                90
_cell_volume                     1693.2(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1824
_cell_measurement_theta_min      3.038
_cell_measurement_theta_max      26.000
_cell_measurement_temperature    296(2)
_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.16
_exptl_crystal_density_diffrn    1.261
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             680
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_absorpt_correction_T_min  0.949
_exptl_absorpt_correction_T_max  0.973
_exptl_special_details           
;
;


_diffrn_ambient_temperature      296(2)
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 0.78
_diffrn_reflns_number            8274
_diffrn_reflns_av_unetI/netI     0.0682
_diffrn_reflns_av_R_equivalents  0.0481
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.038
_diffrn_reflns_theta_max         26.000
_diffrn_reflns_theta_full        26.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?

_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 >
σ(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.
;
_reflns_number_total             3317
_reflns_number_gt                1824
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.1205
_refine_ls_R_factor_gt           0.0669
_refine_ls_wR_factor_ref         0.2136
_refine_ls_wR_factor_gt          0.1769
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.082
_refine_ls_number_reflns         3317
_refine_ls_number_parameters     176
_refine_ls_number_restraints     8
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0915P)²+0.4410P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/6  (Sheldrick, 2015)'
_computing_molecular_graphics    
'ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009)'
_computing_publication_material  
;
WinGX (Farrugia, 1999) and PLATON (Spek, 2009)
;

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.3657(2) 0.5820(4) 0.40591(18) 0.1057(10) Uani 1 1 d . . . . .
O2 O 0.04826(17) 0.7060(3) 0.30121(13) 0.0716(7) Uani 1 1 d . . . . .
N1 N 0.2243(2) 0.6352(4) 0.42572(16) 0.0658(7) Uani 1 1 d . . . . .
H1 H 0.1919 0.6463 0.3747 0.079 Uiso 1 1 calc R U . . .
N2 N 0.17572(19) 0.6584(3) 0.47756(14) 0.0543(6) Uani 1 1 d . . . . .
N3 N -0.07288(18) 0.7682(3) 0.35454(13) 0.0524(6) Uani 1 1 d D . . . .
C1A C 0.3929(4) 0.7412(7) 0.5923(3) 0.0719(6) Uani 0.534(4) 1 d G . P A 1
C2A C 0.3549(4) 0.7424(6) 0.6536(3) 0.0719(6) Uani 0.534(4) 1 d G . P A 1
H2A H 0.3187 0.6396 0.6605 0.086 Uiso 0.534(4) 1 calc R U P A 1
C3A C 0.3712(4) 0.8972(7) 0.7048(3) 0.0719(6) Uani 0.534(4) 1 d G . P A 1
H3A H 0.3458 0.8981 0.7458 0.086 Uiso 0.534(4) 1 calc R U P A 1
C4A C 0.4254(3) 1.0508(6) 0.6945(3) 0.0719(6) Uani 0.534(4) 1 d G . P A 1
H4A H 0.4363 1.1544 0.7287 0.086 Uiso 0.534(4) 1 calc R U P A 1
C5A C 0.4634(3) 1.0496(6) 0.6332(3) 0.0719(6) Uani 0.534(4) 1 d G . P A 1
H5A H 0.4997 1.1524 0.6263 0.086 Uiso 0.534(4) 1 calc R U P A 1
C6A C 0.4471(4) 0.8948(8) 0.5820(3) 0.0719(6) Uani 0.534(4) 1 d G . P A 1
H6A H 0.4725 0.8939 0.5410 0.086 Uiso 0.534(4) 1 calc R U P A 1
C1B C 0.3873(5) 0.7558(7) 0.5906(3) 0.0719(6) Uani 0.466(4) 1 d G . P A 2
C2B C 0.3763(5) 0.7779(7) 0.6643(4) 0.0719(6) Uani 0.466(4) 1 d G . P A 2
H2B H 0.3551 0.6770 0.6873 0.086 Uiso 0.466(4) 1 calc R U P A 2
C3B C 0.3969(5) 0.9510(8) 0.7037(3) 0.0719(6) Uani 0.466(4) 1 d G . P A 2
H3B H 0.3896 0.9658 0.7531 0.086 Uiso 0.466(4) 1 calc R U P A 2
C4B C 0.4286(4) 1.1019(7) 0.6694(3) 0.0719(6) Uani 0.466(4) 1 d G . P A 2
H4B H 0.4425 1.2177 0.6957 0.086 Uiso 0.466(4) 1 calc R U P A 2
C5B C 0.4397(4) 1.0798(7) 0.5956(3) 0.0719(6) Uani 0.466(4) 1 d G . P A 2
H5B H 0.4609 1.1808 0.5726 0.086 Uiso 0.466(4) 1 calc R U P A 2
C6B C 0.4190(4) 0.9068(9) 0.5562(3) 0.0719(6) Uani 0.466(4) 1 d G . P A 2
H6B H 0.4264 0.8920 0.5068 0.086 Uiso 0.466(4) 1 calc R U P A 2
C7 C 0.3748(3) 0.5670(4) 0.5430(2) 0.0725(10) Uani 1 1 d . . . . .
H7A H 0.3346 0.4821 0.5612 0.087 Uiso 1 1 calc R U . A 1
H7B H 0.4384 0.5055 0.5531 0.087 Uiso 1 1 calc R U . A 1
C8 C 0.3241(3) 0.5942(5) 0.4537(2) 0.0710(9) Uani 1 1 d . . . . .
C9 C 0.0828(2) 0.7007(3) 0.44586(16) 0.0483(7) Uani 1 1 d . . . . .
C10 C 0.0170(2) 0.7366(3) 0.48969(16) 0.0468(7) Uani 1 1 d . . . . .
C11 C 0.0326(3) 0.7433(4) 0.57080(17) 0.0557(8) Uani 1 1 d . . . . .
H11 H 0.0950 0.7170 0.6095 0.067 Uiso 1 1 calc R U . . .
C12 C -0.0469(3) 0.7903(4) 0.59292(19) 0.0633(9) Uani 1 1 d . . . . .
H12 H -0.0380 0.7953 0.6473 0.076 Uiso 1 1 calc R U . . .
C13 C -0.1387(3) 0.8295(4) 0.5358(2) 0.0646(9) Uani 1 1 d . . . . .
H13 H -0.1910 0.8604 0.5523 0.078 Uiso 1 1 calc R U . . .
C14 C -0.1558(2) 0.8244(4) 0.45421(19) 0.0577(8) Uani 1 1 d . . . . .
H14 H -0.2182 0.8515 0.4158 0.069 Uiso 1 1 calc R U . . .
C15 C -0.0764(2) 0.7774(3) 0.43232(16) 0.0472(7) Uani 1 1 d . . . . .
C16 C 0.0205(2) 0.7236(4) 0.35830(18) 0.0529(7) Uani 1 1 d . . . . .
C17A C -0.1557(3) 0.8064(5) 0.2797(2) 0.0804(8) Uani 0.534(4) 1 d D . P A 1
H17A H -0.1326 0.8594 0.2395 0.096 Uiso 0.534(4) 1 calc R U P A 1
H17B H -0.2032 0.8925 0.2884 0.096 Uiso 0.534(4) 1 calc R U P A 1
C18A C -0.2039(6) 0.6012(11) 0.2533(4) 0.0804(8) Uani 0.534(4) 1 d D . P A 1
H18A H -0.1563 0.5190 0.2427 0.096 Uiso 0.534(4) 1 calc R U P A 1
H18B H -0.2209 0.5460 0.2964 0.096 Uiso 0.534(4) 1 calc R U P A 1
C19A C -0.2985(5) 0.6203(10) 0.1767(3) 0.0804(8) Uani 0.534(4) 1 d D . P A 1
H19A H -0.3276 0.4980 0.1606 0.121 Uiso 0.534(4) 1 calc R U P A 1
H19B H -0.3456 0.7009 0.1877 0.121 Uiso 0.534(4) 1 calc R U P A 1
H19C H -0.2811 0.6740 0.1341 0.121 Uiso 0.534(4) 1 calc R U P A 1
C17B C -0.1557(3) 0.8064(5) 0.2797(2) 0.0804(8) Uani 0.466(4) 1 d D . P A 2
H17C H -0.1281 0.8128 0.2377 0.096 Uiso 0.466(4) 1 calc R U P A 2
H17D H -0.1793 0.9323 0.2847 0.096 Uiso 0.466(4) 1 calc R U P A 2
C18B C -0.2444(6) 0.6854(12) 0.2489(5) 0.0804(8) Uani 0.466(4) 1 d D . P A 2
H18C H -0.2965 0.7481 0.2052 0.096 Uiso 0.466(4) 1 calc R U P A 2
H18D H -0.2694 0.6582 0.2914 0.096 Uiso 0.466(4) 1 calc R U P A 2
C19B C -0.2147(6) 0.5092(12) 0.2198(5) 0.0804(8) Uani 0.466(4) 1 d D . P A 2
H19D H -0.2713 0.4269 0.1992 0.121 Uiso 0.466(4) 1 calc R U P A 2
H19E H -0.1902 0.5378 0.1778 0.121 Uiso 0.466(4) 1 calc R U P A 2
H19F H -0.1632 0.4482 0.2636 0.121 Uiso 0.466(4) 1 calc R U P A 2


_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
O1 C8 1.211(4) . ?
O2 C16 1.228(3) . ?
N1 N2 1.358(3) . ?
N1 C8 1.370(4) . ?
N1 H1 0.8600 . ?
N2 C9 1.284(4) . ?
N3 C16 1.360(4) . ?
N3 C15 1.407(3) . ?
N3 C17B 1.453(4) . ?
N3 C17A 1.453(4) . ?
C1A C2A 1.3900 . ?
C1A C6A 1.3900 . ?
C1A C7 1.482(5) . ?
C2A C3A 1.3900 . ?
C2A H2A 0.9300 . ?
C3A C4A 1.3900 . ?
C3A H3A 0.9300 . ?
C4A C5A 1.3900 . ?
C4A H4A 0.9300 . ?
C5A C6A 1.3900 . ?
C5A H5A 0.9300 . ?
C6A H6A 0.9300 . ?
C1B C2B 1.3900 . ?
C1B C6B 1.3900 . ?
C1B C7 1.559(5) . ?
C2B C3B 1.3900 . ?
C2B H2B 0.9300 . ?
C3B C4B 1.3900 . ?
C3B H3B 0.9300 . ?
C4B C5B 1.3900 . ?
C4B H4B 0.9300 . ?
C5B C6B 1.3900 . ?
C5B H5B 0.9300 . ?
C6B H6B 0.9300 . ?
C7 C8 1.501(5) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C9 C10 1.454(4) . ?
C9 C16 1.497(4) . ?
C10 C11 1.380(4) . ?
C10 C15 1.390(4) . ?
C11 C12 1.382(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.370(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.384(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.377(4) . ?
C14 H14 0.9300 . ?
C17A C18A 1.606(8) . ?
C17A H17A 0.9700 . ?
C17A H17B 0.9700 . ?
C18A C19A 1.542(8) . ?
C18A H18A 0.9700 . ?
C18A H18B 0.9700 . ?
C19A H19A 0.9600 . ?
C19A H19B 0.9600 . ?
C19A H19C 0.9600 . ?
C17B C18B 1.468(8) . ?
C17B H17C 0.9700 . ?
C17B H17D 0.9700 . ?
C18B C19B 1.473(11) . ?
C18B H18C 0.9700 . ?
C18B H18D 0.9700 . ?
C19B H19D 0.9600 . ?
C19B H19E 0.9600 . ?
C19B H19F 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N2 N1 C8 120.8(3) . . ?
N2 N1 H1 119.6 . . ?
C8 N1 H1 119.6 . . ?
C9 N2 N1 116.3(3) . . ?
C16 N3 C15 110.7(2) . . ?
C16 N3 C17B 123.7(3) . . ?
C15 N3 C17B 125.6(3) . . ?
C16 N3 C17A 123.7(3) . . ?
C15 N3 C17A 125.6(3) . . ?
C2A C1A C6A 120.0 . . ?
C2A C1A C7 115.9(4) . . ?
C6A C1A C7 124.0(4) . . ?
C1A C2A C3A 120.0 . . ?
C1A C2A H2A 120.0 . . ?
C3A C2A H2A 120.0 . . ?
C4A C3A C2A 120.0 . . ?
C4A C3A H3A 120.0 . . ?
C2A C3A H3A 120.0 . . ?
C3A C4A C5A 120.0 . . ?
C3A C4A H4A 120.0 . . ?
C5A C4A H4A 120.0 . . ?
C6A C5A C4A 120.0 . . ?
C6A C5A H5A 120.0 . . ?
C4A C5A H5A 120.0 . . ?
C5A C6A C1A 120.0 . . ?
C5A C6A H6A 120.0 . . ?
C1A C6A H6A 120.0 . . ?
C2B C1B C6B 120.0 . . ?
C2B C1B C7 125.5(4) . . ?
C6B C1B C7 114.3(4) . . ?
C1B C2B C3B 120.0 . . ?
C1B C2B H2B 120.0 . . ?
C3B C2B H2B 120.0 . . ?
C2B C3B C4B 120.0 . . ?
C2B C3B H3B 120.0 . . ?
C4B C3B H3B 120.0 . . ?
C5B C4B C3B 120.0 . . ?
C5B C4B H4B 120.0 . . ?
C3B C4B H4B 120.0 . . ?
C4B C5B C6B 120.0 . . ?
C4B C5B H5B 120.0 . . ?
C6B C5B H5B 120.0 . . ?
C5B C6B C1B 120.0 . . ?
C5B C6B H6B 120.0 . . ?
C1B C6B H6B 120.0 . . ?
C1A C7 C8 115.7(3) . . ?
C8 C7 C1B 112.4(3) . . ?
C1A C7 H7A 108.4 . . ?
C8 C7 H7A 108.4 . . ?
C1A C7 H7B 108.4 . . ?
C8 C7 H7B 108.4 . . ?
H7A C7 H7B 107.4 . . ?
O1 C8 N1 118.9(4) . . ?
O1 C8 C7 124.2(3) . . ?
N1 C8 C7 116.9(3) . . ?
N2 C9 C10 125.7(3) . . ?
N2 C9 C16 127.9(3) . . ?
C10 C9 C16 106.4(3) . . ?
C11 C10 C15 120.4(3) . . ?
C11 C10 C9 132.9(3) . . ?
C15 C10 C9 106.7(2) . . ?
C10 C11 C12 118.2(3) . . ?
C10 C11 H11 120.9 . . ?
C12 C11 H11 120.9 . . ?
C13 C12 C11 120.9(3) . . ?
C13 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
C12 C13 C14 121.8(3) . . ?
C12 C13 H13 119.1 . . ?
C14 C13 H13 119.1 . . ?
C15 C14 C13 117.2(3) . . ?
C15 C14 H14 121.4 . . ?
C13 C14 H14 121.4 . . ?
C14 C15 C10 121.5(3) . . ?
C14 C15 N3 128.5(3) . . ?
C10 C15 N3 109.9(3) . . ?
O2 C16 N3 126.8(3) . . ?
O2 C16 C9 126.9(3) . . ?
N3 C16 C9 106.3(3) . . ?
N3 C17A C18A 102.9(4) . . ?
N3 C17A H17A 111.2 . . ?
C18A C17A H17A 111.2 . . ?
N3 C17A H17B 111.2 . . ?
C18A C17A H17B 111.2 . . ?
H17A C17A H17B 109.1 . . ?
C19A C18A C17A 109.1(6) . . ?
C19A C18A H18A 109.9 . . ?
C17A C18A H18A 109.9 . . ?
C19A C18A H18B 109.9 . . ?
C17A C18A H18B 109.9 . . ?
H18A C18A H18B 108.3 . . ?
C18A C19A H19A 109.5 . . ?
C18A C19A H19B 109.5 . . ?
H19A C19A H19B 109.5 . . ?
C18A C19A H19C 109.5 . . ?
H19A C19A H19C 109.5 . . ?
H19B C19A H19C 109.5 . . ?
N3 C17B C18B 123.0(4) . . ?
N3 C17B H17C 106.6 . . ?
C18B C17B H17C 106.6 . . ?
N3 C17B H17D 106.6 . . ?
C18B C17B H17D 106.6 . . ?
H17C C17B H17D 106.5 . . ?
C17B C18B C19B 107.6(7) . . ?
C17B C18B H18C 110.2 . . ?
C19B C18B H18C 110.2 . . ?
C17B C18B H18D 110.2 . . ?
C19B C18B H18D 110.2 . . ?
H18C C18B H18D 108.5 . . ?
C18B C19B H19D 109.5 . . ?
C18B C19B H19E 109.5 . . ?
H19D C19B H19E 109.5 . . ?
C18B C19B H19F 109.5 . . ?
H19D C19B H19F 109.5 . . ?
H19E C19B H19F 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C8 N1 N2 C9 178.5(3) . . . . ?
C6A C1A C2A C3A 0.0 . . . . ?
C7 C1A C2A C3A 177.8(5) . . . . ?
C1A C2A C3A C4A 0.0 . . . . ?
C2A C3A C4A C5A 0.0 . . . . ?
C3A C4A C5A C6A 0.0 . . . . ?
C4A C5A C6A C1A 0.0 . . . . ?
C2A C1A C6A C5A 0.0 . . . . ?
C7 C1A C6A C5A -177.6(5) . . . . ?
C6B C1B C2B C3B 0.0 . . . . ?
C7 C1B C2B C3B 175.0(5) . . . . ?
C1B C2B C3B C4B 0.0 . . . . ?
C2B C3B C4B C5B 0.0 . . . . ?
C3B C4B C5B C6B 0.0 . . . . ?
C4B C5B C6B C1B 0.0 . . . . ?
C2B C1B C6B C5B 0.0 . . . . ?
C7 C1B C6B C5B -175.5(5) . . . . ?
C2A C1A C7 C8 125.0(3) . . . . ?
C6A C1A C7 C8 -57.4(5) . . . . ?
C2B C1B C7 C8 141.3(4) . . . . ?
C6B C1B C7 C8 -43.4(5) . . . . ?
N2 N1 C8 O1 -177.0(3) . . . . ?
N2 N1 C8 C7 3.0(4) . . . . ?
C1A C7 C8 O1 106.2(4) . . . . ?
C1B C7 C8 O1 108.4(4) . . . . ?
C1A C7 C8 N1 -73.8(4) . . . . ?
C1B C7 C8 N1 -71.7(4) . . . . ?
N1 N2 C9 C10 -178.4(2) . . . . ?
N1 N2 C9 C16 1.4(4) . . . . ?
N2 C9 C10 C11 2.7(4) . . . . ?
C16 C9 C10 C11 -177.1(3) . . . . ?
N2 C9 C10 C15 179.8(3) . . . . ?
C16 C9 C10 C15 0.0(3) . . . . ?
C15 C10 C11 C12 0.4(4) . . . . ?
C9 C10 C11 C12 177.2(3) . . . . ?
C10 C11 C12 C13 -0.2(4) . . . . ?
C11 C12 C13 C14 -0.1(4) . . . . ?
C12 C13 C14 C15 0.2(4) . . . . ?
C13 C14 C15 C10 0.1(4) . . . . ?
C13 C14 C15 N3 -177.7(3) . . . . ?
C11 C10 C15 C14 -0.3(4) . . . . ?
C9 C10 C15 C14 -177.9(2) . . . . ?
C11 C10 C15 N3 177.8(2) . . . . ?
C9 C10 C15 N3 0.2(3) . . . . ?
C16 N3 C15 C14 177.6(3) . . . . ?
C17B N3 C15 C14 -0.6(4) . . . . ?
C17A N3 C15 C14 -0.6(4) . . . . ?
C16 N3 C15 C10 -0.4(3) . . . . ?
C17B N3 C15 C10 -178.6(3) . . . . ?
C17A N3 C15 C10 -178.6(3) . . . . ?
C15 N3 C16 O2 -179.5(3) . . . . ?
C17B N3 C16 O2 -1.3(5) . . . . ?
C17A N3 C16 O2 -1.3(5) . . . . ?
C15 N3 C16 C9 0.4(3) . . . . ?
C17B N3 C16 C9 178.6(2) . . . . ?
C17A N3 C16 C9 178.6(2) . . . . ?
N2 C9 C16 O2 -0.2(5) . . . . ?
C10 C9 C16 O2 179.7(3) . . . . ?
N2 C9 C16 N3 179.9(3) . . . . ?
C10 C9 C16 N3 -0.2(3) . . . . ?
C16 N3 C17A C18A 89.6(4) . . . . ?
C15 N3 C17A C18A -92.5(4) . . . . ?
N3 C17A C18A C19A 176.2(5) . . . . ?
C16 N3 C17B C18B 114.6(5) . . . . ?
C15 N3 C17B C18B -67.5(6) . . . . ?
N3 C17B C18B C19B -72.1(7) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O2 0.86 2.05 2.736(4) 136.4 .

_refine_diff_density_max         0.384
_refine_diff_density_min         -0.313
_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_P5
_database_code_depnum_ccdc_archive 'CCDC 1878546'
loop_
_audit_author_name
_audit_author_address
'Muhammad Nawaz Tahir' 'University of Sargodha'
_audit_update_record             
;
2019-03-29 deposited with the CCDC.	2019-04-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_absolute_configuration .
_chemical_name_systematic        
;
2-Bromo-N'-[(3Z)-2-oxo-1-propyl-1,2-dihydro-3H-indol-3-ylidene]benzohydrazide
;
_chemical_formula_moiety         'C18 H16 Br N3 O2'
_chemical_formula_sum            'C18 H16 Br N3 O2'
_chemical_formula_iupac          'C18 H16 Br N3 O2'
_chemical_formula_weight         386.25

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_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                   7.9365(8)
_cell_length_b                   19.667(2)
_cell_length_c                   10.9290(12)
_cell_angle_alpha                90
_cell_angle_beta                 93.512(4)
_cell_angle_gamma                90
_cell_volume                     1702.7(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2070
_cell_measurement_theta_min      2.135
_cell_measurement_theta_max      27.138
_cell_measurement_temperature    296(2)
_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.15
_exptl_crystal_density_diffrn    1.507
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             784
_exptl_absorpt_coefficient_mu    2.429
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_absorpt_correction_T_min  0.495
_exptl_absorpt_correction_T_max  0.740
_exptl_special_details           
;
;


_diffrn_ambient_temperature      296(2)
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 0.76
_diffrn_reflns_number            13928
_diffrn_reflns_av_unetI/netI     0.0712
_diffrn_reflns_av_R_equivalents  0.0561
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.135
_diffrn_reflns_theta_max         27.138
_diffrn_reflns_theta_full        27.138
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?

_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 >
σ(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.
;
_reflns_number_total             3754
_reflns_number_gt                2070
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.1143
_refine_ls_R_factor_gt           0.0505
_refine_ls_wR_factor_ref         0.1338
_refine_ls_wR_factor_gt          0.1127
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_restrained_S_all      1.008
_refine_ls_number_reflns         3754
_refine_ls_number_parameters     218
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0612P)²+0.2153P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/6  (Sheldrick, 2015)'
_computing_molecular_graphics    
'ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009)'
_computing_publication_material  
;
WinGX (Farrugia, 1999) and PLATON (Spek, 2009)
;

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.08013(5) 0.19779(3) 0.20041(4) 0.0755(2) Uani 1 1 d . . . . .
O1 O 0.3093(3) 0.14438(13) 0.6597(2) 0.0595(7) Uani 1 1 d . . . . .
O2 O 0.4466(3) 0.29024(13) 0.3725(2) 0.0562(7) Uani 1 1 d . . . . .
N1 N 0.2221(4) 0.03220(15) 0.6501(3) 0.0526(8) Uani 1 1 d . . . . .
N2 N 0.3711(4) 0.11729(14) 0.3922(2) 0.0445(7) Uani 1 1 d . . . . .
N3 N 0.3995(4) 0.18260(14) 0.4280(3) 0.0496(8) Uani 1 1 d . . . . .
H3 H 0.3995 0.1933 0.5043 0.059 Uiso 1 1 calc R U . . .
C1 C 0.2867(4) 0.09095(19) 0.6047(3) 0.0472(9) Uani 1 1 d . . . . .
C2 C 0.3219(4) 0.07606(17) 0.4737(3) 0.0425(8) Uani 1 1 d . . . . .
C3 C 0.2785(4) 0.00524(16) 0.4532(3) 0.0433(8) Uani 1 1 d . . . . .
C4 C 0.2837(5) -0.03664(19) 0.3518(3) 0.0589(10) Uani 1 1 d . . . . .
H4 H 0.3258 -0.0208 0.2795 0.071 Uiso 1 1 calc R U . . .
C5 C 0.2252(6) -0.1024(2) 0.3601(4) 0.0725(12) Uani 1 1 d . . . . .
H5 H 0.2279 -0.1312 0.2927 0.087 Uiso 1 1 calc R U . . .
C6 C 0.1631(6) -0.1258(2) 0.4663(4) 0.0746(13) Uani 1 1 d . . . . .
H6 H 0.1227 -0.1702 0.4692 0.090 Uiso 1 1 calc R U . . .
C7 C 0.1588(5) -0.0851(2) 0.5699(4) 0.0663(11) Uani 1 1 d . . . . .
H7 H 0.1186 -0.1015 0.6425 0.080 Uiso 1 1 calc R U . . .
C8 C 0.2168(4) -0.01951(17) 0.5604(3) 0.0480(9) Uani 1 1 d . . . . .
C9 C 0.4281(4) 0.2313(2) 0.3428(3) 0.0423(8) Uani 1 1 d . . . . .
C10 C 0.4366(4) 0.20857(15) 0.2124(3) 0.0392(8) Uani 1 1 d . . . . .
C11 C 0.2970(4) 0.19333(16) 0.1372(3) 0.0431(8) Uani 1 1 d . . . . .
C12 C 0.3097(5) 0.17753(18) 0.0154(3) 0.0542(10) Uani 1 1 d . . . . .
H12 H 0.2137 0.1675 -0.0344 0.065 Uiso 1 1 calc R U . . .
C13 C 0.4665(6) 0.17672(19) -0.0314(4) 0.0646(12) Uani 1 1 d . . . . .
H13 H 0.4765 0.1658 -0.1135 0.078 Uiso 1 1 calc R U . . .
C14 C 0.6077(6) 0.19172(19) 0.0412(4) 0.0637(11) Uani 1 1 d . . . . .
H14 H 0.7136 0.1907 0.0091 0.076 Uiso 1 1 calc R U . . .
C15 C 0.5920(5) 0.20843(17) 0.1624(4) 0.0528(9) Uani 1 1 d . . . . .
H15 H 0.6879 0.2198 0.2113 0.063 Uiso 1 1 calc R U . . .
C16 C 0.1662(5) 0.0251(2) 0.7747(3) 0.0625(11) Uani 1 1 d . . . . .
H16A H 0.0652 -0.0028 0.7725 0.075 Uiso 1 1 calc R U . . .
H16B H 0.1374 0.0696 0.8055 0.075 Uiso 1 1 calc R U . . .
C17 C 0.2985(6) -0.0063(2) 0.8599(4) 0.0733(12) Uani 1 1 d . . . . .
H17A H 0.3963 0.0233 0.8670 0.088 Uiso 1 1 calc R U . . .
H17B H 0.3333 -0.0493 0.8261 0.088 Uiso 1 1 calc R U . . .
C18 C 0.2345(6) -0.0183(3) 0.9868(4) 0.0879(15) Uani 1 1 d . . . . .
H18A H 0.2001 0.0241 1.0206 0.132 Uiso 1 1 calc R U . . .
H18B H 0.3231 -0.0379 1.0393 0.132 Uiso 1 1 calc R U . . .
H18C H 0.1400 -0.0489 0.9804 0.132 Uiso 1 1 calc R U . . .


_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
Br1 C11 1.895(3) . ?
O1 C1 1.219(4) . ?
O2 C9 1.209(4) . ?
N1 C1 1.369(4) . ?
N1 C8 1.411(4) . ?
N1 C16 1.465(4) . ?
N2 C2 1.283(4) . ?
N2 N3 1.358(4) . ?
N3 C9 1.365(4) . ?
N3 H3 0.8600 . ?
C1 C2 1.504(5) . ?
C2 C3 1.449(5) . ?
C3 C4 1.384(5) . ?
C3 C8 1.385(5) . ?
C4 C5 1.380(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.369(6) . ?
C5 H5 0.9300 . ?
C6 C7 1.389(6) . ?
C6 H6 0.9300 . ?
C7 C8 1.377(5) . ?
C7 H7 0.9300 . ?
C9 C10 1.500(5) . ?
C10 C11 1.372(5) . ?
C10 C15 1.379(5) . ?
C11 C12 1.376(5) . ?
C12 C13 1.374(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.365(6) . ?
C13 H13 0.9300 . ?
C14 C15 1.378(5) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 C17 1.494(5) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C18 1.524(6) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C8 110.6(3) . . ?
C1 N1 C16 123.9(3) . . ?
C8 N1 C16 125.4(3) . . ?
C2 N2 N3 116.7(3) . . ?
N2 N3 C9 120.0(3) . . ?
N2 N3 H3 120.0 . . ?
C9 N3 H3 120.0 . . ?
O1 C1 N1 126.6(3) . . ?
O1 C1 C2 127.4(3) . . ?
N1 C1 C2 106.0(3) . . ?
N2 C2 C3 125.4(3) . . ?
N2 C2 C1 128.3(3) . . ?
C3 C2 C1 106.1(3) . . ?
C4 C3 C8 119.8(3) . . ?
C4 C3 C2 132.6(3) . . ?
C8 C3 C2 107.5(3) . . ?
C5 C4 C3 118.6(4) . . ?
C5 C4 H4 120.7 . . ?
C3 C4 H4 120.7 . . ?
C6 C5 C4 120.7(4) . . ?
C6 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
C5 C6 C7 121.7(4) . . ?
C5 C6 H6 119.1 . . ?
C7 C6 H6 119.1 . . ?
C8 C7 C6 117.0(4) . . ?
C8 C7 H7 121.5 . . ?
C6 C7 H7 121.5 . . ?
C7 C8 C3 122.1(3) . . ?
C7 C8 N1 128.3(3) . . ?
C3 C8 N1 109.7(3) . . ?
O2 C9 N3 120.8(3) . . ?
O2 C9 C10 121.9(3) . . ?
N3 C9 C10 117.2(3) . . ?
C11 C10 C15 118.1(3) . . ?
C11 C10 C9 123.6(3) . . ?
C15 C10 C9 118.1(3) . . ?
C10 C11 C12 121.6(3) . . ?
C10 C11 Br1 119.3(3) . . ?
C12 C11 Br1 119.0(3) . . ?
C13 C12 C11 119.0(4) . . ?
C13 C12 H12 120.5 . . ?
C11 C12 H12 120.5 . . ?
C14 C13 C12 120.7(4) . . ?
C14 C13 H13 119.6 . . ?
C12 C13 H13 119.6 . . ?
C13 C14 C15 119.4(4) . . ?
C13 C14 H14 120.3 . . ?
C15 C14 H14 120.3 . . ?
C14 C15 C10 121.1(3) . . ?
C14 C15 H15 119.4 . . ?
C10 C15 H15 119.4 . . ?
N1 C16 C17 112.2(3) . . ?
N1 C16 H16A 109.2 . . ?
C17 C16 H16A 109.2 . . ?
N1 C16 H16B 109.2 . . ?
C17 C16 H16B 109.2 . . ?
H16A C16 H16B 107.9 . . ?
C16 C17 C18 111.8(4) . . ?
C16 C17 H17A 109.3 . . ?
C18 C17 H17A 109.3 . . ?
C16 C17 H17B 109.3 . . ?
C18 C17 H17B 109.3 . . ?
H17A C17 H17B 107.9 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 N2 N3 C9 -170.5(3) . . . . ?
C8 N1 C1 O1 -179.1(3) . . . . ?
C16 N1 C1 O1 1.2(6) . . . . ?
C8 N1 C1 C2 1.4(4) . . . . ?
C16 N1 C1 C2 -178.3(3) . . . . ?
N3 N2 C2 C3 177.4(3) . . . . ?
N3 N2 C2 C1 1.7(5) . . . . ?
O1 C1 C2 N2 -5.3(6) . . . . ?
N1 C1 C2 N2 174.2(3) . . . . ?
O1 C1 C2 C3 178.4(3) . . . . ?
N1 C1 C2 C3 -2.1(4) . . . . ?
N2 C2 C3 C4 3.4(6) . . . . ?
C1 C2 C3 C4 179.9(4) . . . . ?
N2 C2 C3 C8 -174.4(3) . . . . ?
C1 C2 C3 C8 2.1(4) . . . . ?
C8 C3 C4 C5 0.6(5) . . . . ?
C2 C3 C4 C5 -177.0(4) . . . . ?
C3 C4 C5 C6 0.0(6) . . . . ?
C4 C5 C6 C7 -1.0(7) . . . . ?
C5 C6 C7 C8 1.3(6) . . . . ?
C6 C7 C8 C3 -0.6(6) . . . . ?
C6 C7 C8 N1 178.3(4) . . . . ?
C4 C3 C8 C7 -0.3(5) . . . . ?
C2 C3 C8 C7 177.8(3) . . . . ?
C4 C3 C8 N1 -179.4(3) . . . . ?
C2 C3 C8 N1 -1.3(4) . . . . ?
C1 N1 C8 C7 -179.2(4) . . . . ?
C16 N1 C8 C7 0.5(6) . . . . ?
C1 N1 C8 C3 -0.1(4) . . . . ?
C16 N1 C8 C3 179.6(3) . . . . ?
N2 N3 C9 O2 176.9(3) . . . . ?
N2 N3 C9 C10 -3.5(4) . . . . ?
O2 C9 C10 C11 -102.9(4) . . . . ?
N3 C9 C10 C11 77.6(4) . . . . ?
O2 C9 C10 C15 71.5(4) . . . . ?
N3 C9 C10 C15 -108.1(3) . . . . ?
C15 C10 C11 C12 0.7(5) . . . . ?
C9 C10 C11 C12 175.1(3) . . . . ?
C15 C10 C11 Br1 -176.6(2) . . . . ?
C9 C10 C11 Br1 -2.3(4) . . . . ?
C10 C11 C12 C13 0.3(5) . . . . ?
Br1 C11 C12 C13 177.7(3) . . . . ?
C11 C12 C13 C14 -0.4(6) . . . . ?
C12 C13 C14 C15 -0.6(6) . . . . ?
C13 C14 C15 C10 1.7(6) . . . . ?
C11 C10 C15 C14 -1.7(5) . . . . ?
C9 C10 C15 C14 -176.4(3) . . . . ?
C1 N1 C16 C17 -97.5(4) . . . . ?
C8 N1 C16 C17 82.8(5) . . . . ?
N1 C16 C17 C18 -175.7(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N3 H3 O1 0.86 2.11 2.778(4) 133.5 .
C7 H7 Br1 0.93 3.06 3.923(4) 155.3 3_556
C12 H12 O2 0.93 2.44 3.255(5) 146.3 4_565

_refine_diff_density_max         0.455
_refine_diff_density_min         -0.490
_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_P19AJK
_database_code_depnum_ccdc_archive 'CCDC 1878547'
loop_
_audit_author_name
_audit_author_address
'Muhammad Nawaz Tahir' 'University of Sargodha'
_audit_update_record             
;
2019-03-29 deposited with the CCDC.	2019-04-03 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_absolute_configuration .
_chemical_name_systematic        
;
N'-[(3Z)-2-oxo-1-propyl-1,2-dihydro-3H-indol-3-ylidene]furan-2-carbohydrazide
;
_chemical_formula_moiety         'C16 H15 N3 O3'
_chemical_formula_sum            'C16 H15 N3 O3'
_chemical_formula_iupac          'C16 H15 N3 O3'
_chemical_formula_weight         297.31

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   6.977(2)
_cell_length_b                   9.0505(12)
_cell_length_c                   23.689(3)
_cell_angle_alpha                90
_cell_angle_beta                 93.725(5)
_cell_angle_gamma                90
_cell_volume                     1492.6(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1283
_cell_measurement_theta_min      2.835
_cell_measurement_theta_max      27.000
_cell_measurement_temperature    296(2)
_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             624
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_absorpt_correction_T_min  0.939
_exptl_absorpt_correction_T_max  0.977
_exptl_special_details           
;
;


_diffrn_ambient_temperature      296(2)
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker Kappa APEXII CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 0.76
_diffrn_reflns_number            11887
_diffrn_reflns_av_unetI/netI     0.0965
_diffrn_reflns_av_R_equivalents  0.0810
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         2.835
_diffrn_reflns_theta_max         27.000
_diffrn_reflns_theta_full        27.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?

_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 >
σ(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.
;
_reflns_number_total             3241
_reflns_number_gt                1283
_reflns_threshold_expression     I>2σ(I)
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.1855
_refine_ls_R_factor_gt           0.0723
_refine_ls_wR_factor_ref         0.2557
_refine_ls_wR_factor_gt          0.1981
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_refine_ls_number_reflns         3241
_refine_ls_number_parameters     177
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1162P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.020(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_cell_refinement       'SAINT (Bruker, 2007)'
_computing_data_reduction        'SAINT (Bruker, 2007)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/6  (Sheldrick, 2015)'
_computing_molecular_graphics    
'ORTEP-3 for Windows (Farrugia, 1997) and PLATON (Spek, 2009)'
_computing_publication_material  
;
WinGX (Farrugia, 1999) and PLATON (Spek, 2009)
;

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.7831(4) 0.2591(3) -0.03173(10) 0.0845(9) Uani 1 1 d . . . . .
O2 O 0.8942(4) 0.4360(4) 0.16788(13) 0.1101(11) Uani 1 1 d . . . . .
N1 N 0.6945(5) 0.4550(3) -0.09000(13) 0.0743(9) Uani 1 1 d . . . . .
N2 N 0.7977(4) 0.4991(4) 0.05681(14) 0.0712(9) Uani 1 1 d . . . . .
N3 N 0.8371(4) 0.3616(4) 0.07649(12) 0.0736(9) Uani 1 1 d . . . . .
H3A H 0.8349 0.2890 0.0530 0.088 Uiso 1 1 calc R U . . .
C1 C 0.6702(5) 0.6082(4) -0.08358(15) 0.0623(9) Uani 1 1 d . . . . .
C2 C 0.6210(6) 0.7114(5) -0.12382(19) 0.0841(12) Uani 1 1 d . . . . .
H2 H 0.5957 0.6841 -0.1614 0.101 Uiso 1 1 calc R U . . .
C3 C 0.6096(6) 0.8569(5) -0.1077(3) 0.1026(15) Uani 1 1 d . . . . .
H3 H 0.5760 0.9285 -0.1347 0.123 Uiso 1 1 calc R U . . .
C4 C 0.6469(7) 0.8979(5) -0.0523(3) 0.1069(17) Uani 1 1 d . . . . .
H4 H 0.6404 0.9971 -0.0423 0.128 Uiso 1 1 calc R U . . .
C5 C 0.6943(6) 0.7929(5) -0.0109(2) 0.0902(13) Uani 1 1 d . . . . .
H5 H 0.7182 0.8205 0.0268 0.108 Uiso 1 1 calc R U . . .
C6 C 0.7051(5) 0.6466(4) -0.02701(16) 0.0646(10) Uani 1 1 d . . . . .
C7 C 0.7544(5) 0.5111(4) 0.00321(15) 0.0608(9) Uani 1 1 d . . . . .
C8 C 0.7476(5) 0.3905(4) -0.03988(15) 0.0650(10) Uani 1 1 d . . . . .
C9 C 0.8809(5) 0.3339(5) 0.13341(17) 0.0831(12) Uani 1 1 d . . . . .
O3A O 0.9035(8) 0.0699(5) 0.10547(16) 0.0888(8) Uani 0.559(6) 1 d G . P A 1
C10A C 0.9113(5) 0.1775(4) 0.14767(14) 0.0888(8) Uani 0.559(6) 1 d G . P A 1
C11A C 0.9581(9) 0.1080(6) 0.19926(19) 0.0888(8) Uani 0.559(6) 1 d G . P A 1
H11A H 0.9727 0.1540 0.2344 0.107 Uiso 0.559(6) 1 calc R U P A 1
C12A C 0.9792(10) -0.0426(7) 0.1890(3) 0.0888(8) Uani 0.559(6) 1 d G . P A 1
H12A H 1.0104 -0.1147 0.2160 0.107 Uiso 0.559(6) 1 calc R U P A 1
C13A C 0.9455(9) -0.0662(6) 0.1310(2) 0.0888(8) Uani 0.559(6) 1 d G . P A 1
H13A H 0.9501 -0.1568 0.1126 0.107 Uiso 0.559(6) 1 calc R U P A 1
O3B O 0.9681(9) 0.1694(7) 0.2001(2) 0.0888(8) Uani 0.441(6) 1 d G . P A 2
C10B C 0.9113(5) 0.1775(4) 0.14767(14) 0.0888(8) Uani 0.441(6) 1 d G . P A 2
C11B C 0.8816(16) 0.0595(9) 0.1198(3) 0.0888(8) Uani 0.441(6) 1 d G . P A 2
H11B H 0.8354 0.0481 0.0824 0.107 Uiso 0.441(6) 1 calc R U P A 2
C12B C 0.9338(12) -0.0464(9) 0.1583(4) 0.0888(8) Uani 0.441(6) 1 d G . P A 2
H12B H 0.9331 -0.1478 0.1519 0.107 Uiso 0.441(6) 1 calc R U P A 2
C13B C 0.9873(12) 0.0215(9) 0.2079(3) 0.0888(8) Uani 0.441(6) 1 d G . P A 2
H13B H 1.0297 -0.0251 0.2414 0.107 Uiso 0.441(6) 1 calc R U P A 2
C14 C 0.6878(6) 0.3769(5) -0.14548(18) 0.0976(14) Uani 1 1 d . . . B 2
H14A H 0.7250 0.4449 -0.1745 0.117 Uiso 1 1 calc R U . B 2
H14B H 0.7794 0.2962 -0.1434 0.117 Uiso 1 1 calc R U . B 2
C15 C 0.4981(7) 0.3191(6) -0.1612(2) 0.1227(18) Uani 1 1 d . . . B 2
H15A H 0.4038 0.3977 -0.1605 0.147 Uiso 1 1 calc R U . B 2
H15B H 0.4648 0.2437 -0.1344 0.147 Uiso 1 1 calc R U . B 2
C16 C 0.4968(8) 0.2523(6) -0.2214(2) 0.141(2) Uani 1 1 d . . . B 2
H16A H 0.5008 0.3305 -0.2487 0.211 Uiso 1 1 calc R U . B 2
H16B H 0.3820 0.1952 -0.2288 0.211 Uiso 1 1 calc R U . B 2
H16C H 0.6070 0.1897 -0.2240 0.211 Uiso 1 1 calc R U . B 2


_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
O1 C8 1.227(4) . ?
O2 C9 1.233(5) . ?
N1 C8 1.353(4) . ?
N1 C1 1.406(4) . ?
N1 C14 1.490(5) . ?
N2 C7 1.290(5) . ?
N2 N3 1.351(4) . ?
N3 C9 1.386(5) . ?
N3 H3A 0.8600 . ?
C1 C2 1.363(5) . ?
C1 C6 1.391(5) . ?
C2 C3 1.375(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.372(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.390(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.382(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.450(5) . ?
C7 C8 1.493(5) . ?
C9 C10B 1.467(6) . ?
C9 C10A 1.467(6) . ?
O3A C10A 1.394(4) . ?
O3A C13A 1.394(4) . ?
C10A C11A 1.394(4) . ?
C11A C12A 1.395(4) . ?
C11A H11A 0.9300 . ?
C12A C13A 1.395(4) . ?
C12A H12A 0.9300 . ?
C13A H13A 0.9300 . ?
O3B C10B 1.280(7) . ?
O3B C13B 1.357(6) . ?
C10B C11B 1.266(10) . ?
C11B C12B 1.356(6) . ?
C11B H11B 0.9300 . ?
C12B C13B 1.357(6) . ?
C12B H12B 0.9300 . ?
C13B H13B 0.9300 . ?
C14 C15 1.449(6) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.548(6) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 N1 C1 111.0(3) . . ?
C8 N1 C14 124.1(3) . . ?
C1 N1 C14 124.5(3) . . ?
C7 N2 N3 116.5(3) . . ?
N2 N3 C9 121.9(3) . . ?
N2 N3 H3A 119.0 . . ?
C9 N3 H3A 119.0 . . ?
C2 C1 C6 121.6(3) . . ?
C2 C1 N1 128.8(3) . . ?
C6 C1 N1 109.6(3) . . ?
C1 C2 C3 118.6(4) . . ?
C1 C2 H2 120.7 . . ?
C3 C2 H2 120.7 . . ?
C4 C3 C2 121.0(4) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C3 C4 C5 120.8(4) . . ?
C3 C4 H4 119.6 . . ?
C5 C4 H4 119.6 . . ?
C6 C5 C4 118.3(4) . . ?
C6 C5 H5 120.8 . . ?
C4 C5 H5 120.8 . . ?
C5 C6 C1 119.8(4) . . ?
C5 C6 C7 133.6(4) . . ?
C1 C6 C7 106.6(3) . . ?
N2 C7 C6 126.1(3) . . ?
N2 C7 C8 127.3(3) . . ?
C6 C7 C8 106.5(3) . . ?
O1 C8 N1 126.7(3) . . ?
O1 C8 C7 127.1(3) . . ?
N1 C8 C7 106.2(3) . . ?
O2 C9 N3 120.8(4) . . ?
O2 C9 C10B 124.5(4) . . ?
N3 C9 C10B 114.7(4) . . ?
O2 C9 C10A 124.5(4) . . ?
N3 C9 C10A 114.7(4) . . ?
C10A O3A C13A 108.0 . . ?
O3A C10A C11A 108.0 . . ?
O3A C10A C9 120.7(3) . . ?
C11A C10A C9 131.2(3) . . ?
C10A C11A C12A 108.0 . . ?
C10A C11A H11A 126.0 . . ?
C12A C11A H11A 126.0 . . ?
C11A C12A C13A 108.0 . . ?
C11A C12A H12A 126.0 . . ?
C13A C12A H12A 126.0 . . ?
O3A C13A C12A 108.0 . . ?
O3A C13A H13A 126.0 . . ?
C12A C13A H13A 126.0 . . ?
C10B O3B C13B 102.2(4) . . ?
C11B C10B O3B 119.1(6) . . ?
C11B C10B C9 132.7(5) . . ?
O3B C10B C9 108.0(4) . . ?
C10B C11B C12B 102.6(3) . . ?
C10B C11B H11B 128.7 . . ?
C12B C11B H11B 128.7 . . ?
C11B C12B C13B 108.0 . . ?
C11B C12B H12B 126.0 . . ?
C13B C12B H12B 126.0 . . ?
O3B C13B C12B 108.0 . . ?
O3B C13B H13B 126.0 . . ?
C12B C13B H13B 126.0 . . ?
C15 C14 N1 111.9(4) . . ?
C15 C14 H14A 109.2 . . ?
N1 C14 H14A 109.2 . . ?
C15 C14 H14B 109.2 . . ?
N1 C14 H14B 109.2 . . ?
H14A C14 H14B 107.9 . . ?
C14 C15 C16 109.1(4) . . ?
C14 C15 H15A 109.9 . . ?
C16 C15 H15A 109.9 . . ?
C14 C15 H15B 109.9 . . ?
C16 C15 H15B 109.9 . . ?
H15A C15 H15B 108.3 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 N2 N3 C9 -178.4(3) . . . . ?
C8 N1 C1 C2 178.8(4) . . . . ?
C14 N1 C1 C2 6.2(6) . . . . ?
C8 N1 C1 C6 -1.1(4) . . . . ?
C14 N1 C1 C6 -173.7(3) . . . . ?
C6 C1 C2 C3 1.2(5) . . . . ?
N1 C1 C2 C3 -178.6(3) . . . . ?
C1 C2 C3 C4 0.1(6) . . . . ?
C2 C3 C4 C5 -1.0(7) . . . . ?
C3 C4 C5 C6 0.8(6) . . . . ?
C4 C5 C6 C1 0.5(5) . . . . ?
C4 C5 C6 C7 178.0(4) . . . . ?
C2 C1 C6 C5 -1.5(5) . . . . ?
N1 C1 C6 C5 178.4(3) . . . . ?
C2 C1 C6 C7 -179.6(3) . . . . ?
N1 C1 C6 C7 0.3(4) . . . . ?
N3 N2 C7 C6 179.3(3) . . . . ?
N3 N2 C7 C8 -1.7(5) . . . . ?
C5 C6 C7 N2 2.0(6) . . . . ?
C1 C6 C7 N2 179.7(3) . . . . ?
C5 C6 C7 C8 -177.2(4) . . . . ?
C1 C6 C7 C8 0.5(3) . . . . ?
C1 N1 C8 O1 -178.6(3) . . . . ?
C14 N1 C8 O1 -6.0(6) . . . . ?
C1 N1 C8 C7 1.4(4) . . . . ?
C14 N1 C8 C7 174.0(3) . . . . ?
N2 C7 C8 O1 -0.4(6) . . . . ?
C6 C7 C8 O1 178.8(3) . . . . ?
N2 C7 C8 N1 179.6(3) . . . . ?
C6 C7 C8 N1 -1.1(3) . . . . ?
N2 N3 C9 O2 -3.4(5) . . . . ?
N2 N3 C9 C10B 177.4(3) . . . . ?
N2 N3 C9 C10A 177.4(3) . . . . ?
C13A O3A C10A C11A 0.0 . . . . ?
C13A O3A C10A C9 177.5(4) . . . . ?
O2 C9 C10A O3A -176.5(4) . . . . ?
N3 C9 C10A O3A 2.6(5) . . . . ?
O2 C9 C10A C11A 0.4(6) . . . . ?
N3 C9 C10A C11A 179.5(4) . . . . ?
O3A C10A C11A C12A 0.0 . . . . ?
C9 C10A C11A C12A -177.2(4) . . . . ?
C10A C11A C12A C13A 0.0 . . . . ?
C10A O3A C13A C12A 0.0 . . . . ?
C11A C12A C13A O3A 0.0 . . . . ?
C13B O3B C10B C11B 3.0(10) . . . . ?
C13B O3B C10B C9 179.0(4) . . . . ?
O2 C9 C10B C11B 170.0(8) . . . . ?
N3 C9 C10B C11B -10.8(10) . . . . ?
O2 C9 C10B O3B -5.2(6) . . . . ?
N3 C9 C10B O3B 173.9(4) . . . . ?
O3B C10B C11B C12B -3.0(10) . . . . ?
C9 C10B C11B C12B -177.8(5) . . . . ?
C10B C11B C12B C13B 1.6(5) . . . . ?
C10B O3B C13B C12B -1.6(5) . . . . ?
C11B C12B C13B O3B 0.0 . . . . ?
C8 N1 C14 C15 94.0(5) . . . . ?
C1 N1 C14 C15 -94.3(5) . . . . ?
N1 C14 C15 C16 174.9(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N3 H3A O1 0.86 2.03 2.729(4) 137.3 .
C13B H13B O2 0.93 2.21 3.102(6) 161.1 2_745
C15 H15A O2 0.97 2.56 3.517(6) 167.8 3_665

_refine_diff_density_max         0.329
_refine_diff_density_min         -0.260
_refine_diff_density_rms         0.041

