# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_asif-pyno2
_audit_block_doi                 10.5517/ccdc.csd.cc1kqk3y
_database_code_depnum_ccdc_archive 'CCDC 1451640'
loop_
_audit_author_name
_audit_author_address
'Asif Ali'
;CSIR TKDL New Delhi
India
;
_audit_update_record             
;
2020-04-21 deposited with the CCDC.	2021-01-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C23 H16 N2 O3'
_chemical_formula_sum            'C23 H16 N2 O3'
_chemical_formula_weight         368.38

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'

_symmetry_cell_setting           MONOCLINIC
_symmetry_space_group_name_H-M   C2/c
_symmetry_space_group_name_HALL  '-C 2yc'

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

_cell_length_a                   22.076(2)
_cell_length_b                   10.1079(8)
_cell_length_c                   16.921(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 107.250(11)
_cell_angle_gamma                90.00
_cell_volume                     3605.9(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1788
_cell_measurement_theta_min      3.9380
_cell_measurement_theta_max      27.5720

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            WHITE
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.357
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1536
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.89320
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.1049
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            7234
_diffrn_reflns_av_R_equivalents  0.0280
_diffrn_reflns_av_sigmaI/netI    0.0481
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         3.53
_diffrn_reflns_theta_max         26.00
_reflns_number_total             3530
_reflns_number_gt                2176
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro (Oxford Diffraction,2010)'
_computing_cell_refinement       'CrysAlisPro (Oxford Diffraction,2010)'
_computing_data_reduction        'CrysAlisPro (Oxford Diffraction,2010)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'ORTEP3 (Farrugia, 2012)'
_computing_publication_material  '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)+(0.0433P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    CONSTR
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.0015(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3530
_refine_ls_number_parameters     254
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0848
_refine_ls_R_factor_gt           0.0445
_refine_ls_wR_factor_ref         0.1090
_refine_ls_wR_factor_gt          0.0911
_refine_ls_goodness_of_fit_ref   0.993
_refine_ls_restrained_S_all      0.993
_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
N1 N 0.07292(7) 0.64452(13) 0.06170(9) 0.0454(4) Uani 1 1 d . . .
O3 O 0.04066(7) 0.86042(11) 0.02876(10) 0.0693(5) Uani 1 1 d . . .
C2 C 0.06361(8) 0.52734(15) 0.09449(10) 0.0380(4) Uani 1 1 d . . .
C3 C 0.01392(8) 0.51012(15) 0.12704(10) 0.0403(4) Uani 1 1 d . . .
H3 H 0.0087 0.4289 0.1500 0.048 Uiso 1 1 calc R . .
C5 C -0.01783(9) 0.73149(15) 0.09388(11) 0.0451(5) Uani 1 1 d . . .
H5 H -0.0440 0.8038 0.0931 0.054 Uiso 1 1 calc R . .
C4 C -0.02856(8) 0.61184(15) 0.12624(10) 0.0384(4) Uani 1 1 d . . .
C7 C 0.10875(8) 0.42061(16) 0.09241(10) 0.0408(4) Uani 1 1 d . . .
C23 C -0.15817(9) 0.65933(17) 0.22529(11) 0.0451(5) Uani 1 1 d . . .
N2 N -0.18189(9) 0.76312(18) 0.26840(10) 0.0608(5) Uani 1 1 d . . .
C6 C 0.03322(9) 0.74051(16) 0.06253(12) 0.0461(5) Uani 1 1 d . . .
C19 C -0.08403(8) 0.58897(16) 0.15658(10) 0.0395(4) Uani 1 1 d . . .
O1 O -0.22553(8) 0.73630(15) 0.29636(10) 0.0831(5) Uani 1 1 d . . .
C24 C -0.10740(8) 0.68728(16) 0.19652(10) 0.0431(5) Uani 1 1 d . . .
H24 H -0.0891 0.7710 0.2038 0.052 Uiso 1 1 calc R . .
C20 C -0.11386(9) 0.46633(17) 0.14607(11) 0.0485(5) Uani 1 1 d . . .
H20 H -0.0991 0.3995 0.1187 0.058 Uiso 1 1 calc R . .
O2 O -0.15677(8) 0.87159(14) 0.27580(10) 0.0848(6) Uani 1 1 d . . .
C8 C 0.16097(9) 0.44497(18) 0.06576(12) 0.0544(5) Uani 1 1 d . . .
H8 H 0.1689 0.5306 0.0514 0.065 Uiso 1 1 calc R . .
C13 C 0.07964(11) 0.87191(16) -0.02239(14) 0.0528(5) Uani 1 1 d . . .
C22 C -0.18739(9) 0.53784(18) 0.21563(12) 0.0530(5) Uani 1 1 d . . .
H22 H -0.2215 0.5216 0.2359 0.064 Uiso 1 1 calc R . .
C9 C 0.20152(10) 0.3444(2) 0.06016(14) 0.0686(6) Uani 1 1 d . . .
H9 H 0.2366 0.3627 0.0424 0.082 Uiso 1 1 calc R . .
C12 C 0.09998(10) 0.29257(17) 0.11487(13) 0.0604(6) Uani 1 1 d . . .
H12 H 0.0659 0.2739 0.1347 0.073 Uiso 1 1 calc R . .
C21 C -0.16465(9) 0.44149(18) 0.17512(12) 0.0552(5) Uani 1 1 d . . .
H21 H -0.1837 0.3585 0.1672 0.066 Uiso 1 1 calc R . .
C10 C 0.19051(10) 0.2175(2) 0.08059(13) 0.0641(6) Uani 1 1 d . . .
H10 H 0.2173 0.1493 0.0752 0.077 Uiso 1 1 calc R . .
C11 C 0.14004(11) 0.19203(19) 0.10882(14) 0.0683(6) Uani 1 1 d . . .
H11 H 0.1327 0.1064 0.1240 0.082 Uiso 1 1 calc R . .
C18 C 0.14423(11) 0.85987(17) 0.00777(14) 0.0628(6) Uani 1 1 d . . .
H18 H 0.1633 0.8382 0.0630 0.075 Uiso 1 1 calc R . .
C14 C 0.05127(11) 0.90638(18) -0.10286(15) 0.0660(6) Uani 1 1 d . . .
H14 H 0.0075 0.9158 -0.1225 0.079 Uiso 1 1 calc R . .
C17 C 0.18064(11) 0.88015(19) -0.04455(17) 0.0722(7) Uani 1 1 d . . .
H17 H 0.2245 0.8717 -0.0247 0.087 Uiso 1 1 calc R . .
C16 C 0.15250(14) 0.91282(19) -0.12572(17) 0.0752(7) Uani 1 1 d . . .
H16 H 0.1772 0.9253 -0.1611 0.090 Uiso 1 1 calc R . .
C15 C 0.08811(13) 0.9270(2) -0.15469(15) 0.0757(7) Uani 1 1 d . . .
H15 H 0.0691 0.9507 -0.2096 0.091 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 C6 1.310(2) . ?
N1 C2 1.3493(19) . ?
O3 C6 1.3704(19) . ?
O3 C13 1.395(2) . ?
C2 C3 1.377(2) . ?
C2 C7 1.476(2) . ?
C3 C4 1.389(2) . ?
C3 H3 0.9300 . ?
C5 C4 1.377(2) . ?
C5 C6 1.384(2) . ?
C5 H5 0.9300 . ?
C4 C19 1.480(2) . ?
C7 C12 1.379(2) . ?
C7 C8 1.379(2) . ?
C23 C22 1.374(2) . ?
C23 C24 1.377(2) . ?
C23 N2 1.460(2) . ?
N2 O2 1.218(2) . ?
N2 O1 1.2232(19) . ?
C19 C24 1.385(2) . ?
C19 C20 1.390(2) . ?
C24 H24 0.9300 . ?
C20 C21 1.374(2) . ?
C20 H20 0.9300 . ?
C8 C9 1.377(2) . ?
C8 H8 0.9300 . ?
C13 C14 1.364(3) . ?
C13 C18 1.370(3) . ?
C22 C21 1.369(2) . ?
C22 H22 0.9300 . ?
C9 C10 1.368(3) . ?
C9 H9 0.9300 . ?
C12 C11 1.371(3) . ?
C12 H12 0.9300 . ?
C21 H21 0.9300 . ?
C10 C11 1.361(3) . ?
C10 H10 0.9300 . ?
C11 H11 0.9300 . ?
C18 C17 1.376(3) . ?
C18 H18 0.9300 . ?
C14 C15 1.377(3) . ?
C14 H14 0.9300 . ?
C17 C16 1.369(3) . ?
C17 H17 0.9300 . ?
C16 C15 1.367(3) . ?
C16 H16 0.9300 . ?
C15 H15 0.9300 . ?

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
C6 N1 C2 117.50(14) . . ?
C6 O3 C13 120.31(13) . . ?
N1 C2 C3 120.80(15) . . ?
N1 C2 C7 116.46(14) . . ?
C3 C2 C7 122.73(14) . . ?
C2 C3 C4 121.21(15) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?
C4 C5 C6 117.78(15) . . ?
C4 C5 H5 121.1 . . ?
C6 C5 H5 121.1 . . ?
C5 C4 C3 117.32(15) . . ?
C5 C4 C19 122.20(15) . . ?
C3 C4 C19 120.45(14) . . ?
C12 C7 C8 117.21(16) . . ?
C12 C7 C2 121.91(15) . . ?
C8 C7 C2 120.87(15) . . ?
C22 C23 C24 122.94(16) . . ?
C22 C23 N2 118.44(16) . . ?
C24 C23 N2 118.62(17) . . ?
O2 N2 O1 123.12(17) . . ?
O2 N2 C23 118.57(17) . . ?
O1 N2 C23 118.30(18) . . ?
N1 C6 O3 119.16(15) . . ?
N1 C6 C5 125.36(15) . . ?
O3 C6 C5 115.47(15) . . ?
C24 C19 C20 118.14(15) . . ?
C24 C19 C4 121.58(15) . . ?
C20 C19 C4 120.28(14) . . ?
C23 C24 C19 119.04(16) . . ?
C23 C24 H24 120.5 . . ?
C19 C24 H24 120.5 . . ?
C21 C20 C19 121.53(16) . . ?
C21 C20 H20 119.2 . . ?
C19 C20 H20 119.2 . . ?
C9 C8 C7 120.95(18) . . ?
C9 C8 H8 119.5 . . ?
C7 C8 H8 119.5 . . ?
C14 C13 C18 120.88(19) . . ?
C14 C13 O3 117.1(2) . . ?
C18 C13 O3 121.8(2) . . ?
C21 C22 C23 117.80(16) . . ?
C21 C22 H22 121.1 . . ?
C23 C22 H22 121.1 . . ?
C10 C9 C8 120.46(19) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
C11 C12 C7 121.93(18) . . ?
C11 C12 H12 119.0 . . ?
C7 C12 H12 119.0 . . ?
C22 C21 C20 120.55(17) . . ?
C22 C21 H21 119.7 . . ?
C20 C21 H21 119.7 . . ?
C11 C10 C9 119.45(18) . . ?
C11 C10 H10 120.3 . . ?
C9 C10 H10 120.3 . . ?
C10 C11 C12 119.95(19) . . ?
C10 C11 H11 120.0 . . ?
C12 C11 H11 120.0 . . ?
C13 C18 C17 119.3(2) . . ?
C13 C18 H18 120.4 . . ?
C17 C18 H18 120.4 . . ?
C13 C14 C15 119.4(2) . . ?
C13 C14 H14 120.3 . . ?
C15 C14 H14 120.3 . . ?
C16 C17 C18 120.2(2) . . ?
C16 C17 H17 119.9 . . ?
C18 C17 H17 119.9 . . ?
C15 C16 C17 120.0(2) . . ?
C15 C16 H16 120.0 . . ?
C17 C16 H16 120.0 . . ?
C16 C15 C14 120.2(2) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?

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
C6 N1 C2 C3 0.3(3) . . . . ?
C6 N1 C2 C7 179.68(16) . . . . ?
N1 C2 C3 C4 0.8(3) . . . . ?
C7 C2 C3 C4 -178.48(16) . . . . ?
C6 C5 C4 C3 1.8(3) . . . . ?
C6 C5 C4 C19 -176.12(16) . . . . ?
C2 C3 C4 C5 -1.9(3) . . . . ?
C2 C3 C4 C19 176.04(16) . . . . ?
N1 C2 C7 C12 -172.18(18) . . . . ?
C3 C2 C7 C12 7.2(3) . . . . ?
N1 C2 C7 C8 6.2(3) . . . . ?
C3 C2 C7 C8 -174.43(17) . . . . ?
C22 C23 N2 O2 -178.76(18) . . . . ?
C24 C23 N2 O2 1.6(3) . . . . ?
C22 C23 N2 O1 2.2(3) . . . . ?
C24 C23 N2 O1 -177.46(17) . . . . ?
C2 N1 C6 O3 -179.11(17) . . . . ?
C2 N1 C6 C5 -0.4(3) . . . . ?
C13 O3 C6 N1 14.9(3) . . . . ?
C13 O3 C6 C5 -163.97(18) . . . . ?
C4 C5 C6 N1 -0.7(3) . . . . ?
C4 C5 C6 O3 178.06(17) . . . . ?
C5 C4 C19 C24 -36.1(3) . . . . ?
C3 C4 C19 C24 146.06(17) . . . . ?
C5 C4 C19 C20 144.46(18) . . . . ?
C3 C4 C19 C20 -33.4(2) . . . . ?
C22 C23 C24 C19 -0.6(3) . . . . ?
N2 C23 C24 C19 179.13(16) . . . . ?
C20 C19 C24 C23 1.1(3) . . . . ?
C4 C19 C24 C23 -178.37(16) . . . . ?
C24 C19 C20 C21 -0.8(3) . . . . ?
C4 C19 C20 C21 178.65(17) . . . . ?
C12 C7 C8 C9 1.5(3) . . . . ?
C2 C7 C8 C9 -176.98(19) . . . . ?
C6 O3 C13 C14 115.9(2) . . . . ?
C6 O3 C13 C18 -69.3(2) . . . . ?
C24 C23 C22 C21 -0.3(3) . . . . ?
N2 C23 C22 C21 -179.99(17) . . . . ?
C7 C8 C9 C10 0.4(3) . . . . ?
C8 C7 C12 C11 -2.0(3) . . . . ?
C2 C7 C12 C11 176.49(19) . . . . ?
C23 C22 C21 C20 0.6(3) . . . . ?
C19 C20 C21 C22 -0.1(3) . . . . ?
C8 C9 C10 C11 -1.9(4) . . . . ?
C9 C10 C11 C12 1.4(4) . . . . ?
C7 C12 C11 C10 0.5(4) . . . . ?
C14 C13 C18 C17 -1.4(3) . . . . ?
O3 C13 C18 C17 -176.05(17) . . . . ?
C18 C13 C14 C15 1.1(3) . . . . ?
O3 C13 C14 C15 176.02(16) . . . . ?
C13 C18 C17 C16 0.4(3) . . . . ?
C18 C17 C16 C15 0.9(3) . . . . ?
C17 C16 C15 C14 -1.1(3) . . . . ?
C13 C14 C15 C16 0.1(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.158
_refine_diff_density_min         -0.126
_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_asif-py-py-2
_audit_block_doi                 10.5517/ccdc.csd.cc1kqk2x
_database_code_depnum_ccdc_archive 'CCDC 1451639'
loop_
_audit_author_name
_audit_author_address
'Asif Ali'
;CSIR TKDL New Delhi
India
;
_audit_update_record             
;
2020-04-21 deposited with the CCDC.	2021-01-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H16 N2 O'
_chemical_formula_sum            'C22 H16 N2 O'
_chemical_formula_weight         324.37

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'

_symmetry_cell_setting           TRICLINIC
_symmetry_space_group_name_H-M   P-1
_symmetry_space_group_name_HALL  -P1

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

_cell_length_a                   8.1694(12)
_cell_length_b                   9.7524(16)
_cell_length_c                   11.8980(18)
_cell_angle_alpha                73.012(14)
_cell_angle_beta                 75.211(13)
_cell_angle_gamma                67.352(15)
_cell_volume                     825.6(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1471
_cell_measurement_theta_min      4.1210
_cell_measurement_theta_max      26.0950

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            WHITE
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.305
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             340
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.86769
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'Omega Scan'
_diffrn_detector_area_resol_mean 16.1049
_diffrn_standards_number         0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_decay_%        0
_diffrn_reflns_number            5807
_diffrn_reflns_av_R_equivalents  0.0281
_diffrn_reflns_av_sigmaI/netI    0.0564
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.52
_diffrn_reflns_theta_max         26.00
_reflns_number_total             3223
_reflns_number_gt                1919
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro (Oxford Diffraction,2010)'
_computing_cell_refinement       'CrysAlisPro (Oxford Diffraction,2010)'
_computing_data_reduction        'CrysAlisPro (Oxford Diffraction,2010)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'ORTEP3 (Farrugia, 2012)'
_computing_publication_material  '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)+(0.0580P)²+0.0032P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    CONSTR
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.039(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3223
_refine_ls_number_parameters     227
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0945
_refine_ls_R_factor_gt           0.0533
_refine_ls_wR_factor_ref         0.1519
_refine_ls_wR_factor_gt          0.1235
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_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 0.3478(3) 0.8635(2) -0.00625(16) 0.0432(5) Uani 1 1 d . . .
H1 H 0.3643 0.9576 -0.0333 0.052 Uiso 1 1 calc R . .
C4 C 0.3015(2) 0.5874(2) 0.08370(16) 0.0399(5) Uani 1 1 d . . .
N3 N 0.3870(2) 0.6321(2) 0.14242(14) 0.0444(5) Uani 1 1 d . . .
C19 C 0.2802(2) 0.4378(2) 0.13637(17) 0.0424(5) Uani 1 1 d . . .
O1 O 0.4980(2) 0.81204(17) 0.15141(12) 0.0609(5) Uani 1 1 d . . .
C5 C 0.2398(3) 0.6764(2) -0.02024(17) 0.0434(5) Uani 1 1 d . . .
H5 H 0.1835 0.6417 -0.0595 0.052 Uiso 1 1 calc R . .
C6 C 0.2611(3) 0.8173(2) -0.06664(16) 0.0411(5) Uani 1 1 d . . .
N20 N 0.2098(2) 0.3867(2) 0.07378(15) 0.0521(5) Uani 1 1 d . . .
C24 C 0.3327(3) 0.3538(3) 0.24399(19) 0.0550(6) Uani 1 1 d . . .
H24 H 0.3806 0.3918 0.2863 0.066 Uiso 1 1 calc R . .
C7 C 0.1943(3) 0.9159(2) -0.17783(17) 0.0432(5) Uani 1 1 d . . .
C2 C 0.4087(3) 0.7641(3) 0.09603(18) 0.0460(6) Uani 1 1 d . . .
C22 C 0.2422(3) 0.1603(3) 0.2248(2) 0.0660(7) Uani 1 1 d . . .
H22 H 0.2276 0.0655 0.2527 0.079 Uiso 1 1 calc R . .
C21 C 0.1927(3) 0.2507(3) 0.1189(2) 0.0600(7) Uani 1 1 d . . .
H21 H 0.1439 0.2146 0.0757 0.072 Uiso 1 1 calc R . .
C12 C 0.1114(3) 1.0709(3) -0.18974(18) 0.0555(6) Uani 1 1 d . . .
H12 H 0.0968 1.1150 -0.1267 0.067 Uiso 1 1 calc R . .
C13 C 0.5798(3) 0.7112(3) 0.24783(18) 0.0510(6) Uani 1 1 d . . .
C8 C 0.2132(3) 0.8528(3) -0.27281(18) 0.0549(6) Uani 1 1 d . . .
H8 H 0.2657 0.7481 -0.2660 0.066 Uiso 1 1 calc R . .
C9 C 0.1546(3) 0.9446(3) -0.37722(19) 0.0652(7) Uani 1 1 d . . .
H9 H 0.1706 0.9020 -0.4413 0.078 Uiso 1 1 calc R . .
C18 C 0.7371(3) 0.5966(3) 0.2304(2) 0.0595(7) Uani 1 1 d . . .
H18 H 0.7882 0.5786 0.1544 0.071 Uiso 1 1 calc R . .
C23 C 0.3136(3) 0.2129(3) 0.2883(2) 0.0670(7) Uani 1 1 d . . .
H23 H 0.3490 0.1542 0.3607 0.080 Uiso 1 1 calc R . .
C17 C 0.8199(3) 0.5072(3) 0.3271(2) 0.0685(8) Uani 1 1 d . . .
H17 H 0.9272 0.4274 0.3166 0.082 Uiso 1 1 calc R . .
C11 C 0.0499(3) 1.1615(3) -0.2936(2) 0.0683(7) Uani 1 1 d . . .
H11 H -0.0073 1.2658 -0.2999 0.082 Uiso 1 1 calc R . .
C10 C 0.0729(3) 1.0984(3) -0.3871(2) 0.0717(8) Uani 1 1 d . . .
H10 H 0.0330 1.1598 -0.4576 0.086 Uiso 1 1 calc R . .
C14 C 0.5040(4) 0.7407(3) 0.3574(2) 0.0819(10) Uani 1 1 d . . .
H14 H 0.3968 0.8205 0.3678 0.098 Uiso 1 1 calc R . .
C16 C 0.7462(4) 0.5349(3) 0.4374(2) 0.0809(9) Uani 1 1 d . . .
H16 H 0.8030 0.4751 0.5024 0.097 Uiso 1 1 calc R . .
C15 C 0.5877(4) 0.6512(4) 0.4523(2) 0.1031(13) Uani 1 1 d . . .
H15 H 0.5361 0.6696 0.5280 0.124 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 C6 1.384(3) . ?
C1 C2 1.385(3) . ?
C1 H1 0.9300 . ?
C4 N3 1.351(2) . ?
C4 C5 1.375(2) . ?
C4 C19 1.469(3) . ?
N3 C2 1.306(3) . ?
C19 N20 1.338(2) . ?
C19 C24 1.375(3) . ?
O1 C2 1.369(2) . ?
O1 C13 1.399(2) . ?
C5 C6 1.384(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.481(3) . ?
N20 C21 1.325(3) . ?
C24 C23 1.375(3) . ?
C24 H24 0.9300 . ?
C7 C12 1.379(3) . ?
C7 C8 1.387(3) . ?
C22 C23 1.362(3) . ?
C22 C21 1.366(3) . ?
C22 H22 0.9300 . ?
C21 H21 0.9300 . ?
C12 C11 1.378(3) . ?
C12 H12 0.9300 . ?
C13 C18 1.355(3) . ?
C13 C14 1.355(3) . ?
C8 C9 1.378(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.369(4) . ?
C9 H9 0.9300 . ?
C18 C17 1.379(3) . ?
C18 H18 0.9300 . ?
C23 H23 0.9300 . ?
C17 C16 1.355(3) . ?
C17 H17 0.9300 . ?
C11 C10 1.362(3) . ?
C11 H11 0.9300 . ?
C10 H10 0.9300 . ?
C14 C15 1.364(3) . ?
C14 H14 0.9300 . ?
C16 C15 1.365(3) . ?
C16 H16 0.9300 . ?
C15 H15 0.9300 . ?

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
C6 C1 C2 117.3(2) . . ?
C6 C1 H1 121.3 . . ?
C2 C1 H1 121.3 . . ?
N3 C4 C5 121.9(2) . . ?
N3 C4 C19 116.25(17) . . ?
C5 C4 C19 121.89(18) . . ?
C2 N3 C4 116.98(17) . . ?
N20 C19 C24 121.8(2) . . ?
N20 C19 C4 116.74(18) . . ?
C24 C19 C4 121.42(19) . . ?
C2 O1 C13 118.76(18) . . ?
C4 C5 C6 120.19(18) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C1 C6 C5 118.00(18) . . ?
C1 C6 C7 120.8(2) . . ?
C5 C6 C7 121.24(18) . . ?
C21 N20 C19 117.58(19) . . ?
C23 C24 C19 119.2(2) . . ?
C23 C24 H24 120.4 . . ?
C19 C24 H24 120.4 . . ?
C12 C7 C8 118.37(18) . . ?
C12 C7 C6 121.49(18) . . ?
C8 C7 C6 120.14(19) . . ?
N3 C2 O1 118.81(18) . . ?
N3 C2 C1 125.6(2) . . ?
O1 C2 C1 115.6(2) . . ?
C23 C22 C21 118.2(3) . . ?
C23 C22 H22 120.9 . . ?
C21 C22 H22 120.9 . . ?
N20 C21 C22 124.0(2) . . ?
N20 C21 H21 118.0 . . ?
C22 C21 H21 118.0 . . ?
C11 C12 C7 121.0(2) . . ?
C11 C12 H12 119.5 . . ?
C7 C12 H12 119.5 . . ?
C18 C13 C14 121.6(2) . . ?
C18 C13 O1 120.82(19) . . ?
C14 C13 O1 117.4(2) . . ?
C9 C8 C7 120.2(2) . . ?
C9 C8 H8 119.9 . . ?
C7 C8 H8 119.9 . . ?
C10 C9 C8 120.3(2) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
C13 C18 C17 118.8(2) . . ?
C13 C18 H18 120.6 . . ?
C17 C18 H18 120.6 . . ?
C22 C23 C24 119.1(2) . . ?
C22 C23 H23 120.4 . . ?
C24 C23 H23 120.4 . . ?
C16 C17 C18 120.4(2) . . ?
C16 C17 H17 119.8 . . ?
C18 C17 H17 119.8 . . ?
C10 C11 C12 120.0(2) . . ?
C10 C11 H11 120.0 . . ?
C12 C11 H11 120.0 . . ?
C11 C10 C9 120.0(2) . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
C13 C14 C15 118.9(2) . . ?
C13 C14 H14 120.6 . . ?
C15 C14 H14 120.6 . . ?
C17 C16 C15 119.4(2) . . ?
C17 C16 H16 120.3 . . ?
C15 C16 H16 120.3 . . ?
C14 C15 C16 120.9(2) . . ?
C14 C15 H15 119.6 . . ?
C16 C15 H15 119.6 . . ?

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
C5 C4 N3 C2 0.0(3) . . . . ?
C19 C4 N3 C2 179.28(17) . . . . ?
N3 C4 C19 N20 -174.42(15) . . . . ?
C5 C4 C19 N20 4.9(3) . . . . ?
N3 C4 C19 C24 4.7(3) . . . . ?
C5 C4 C19 C24 -176.05(17) . . . . ?
N3 C4 C5 C6 -1.3(3) . . . . ?
C19 C4 C5 C6 179.50(17) . . . . ?
C2 C1 C6 C5 0.7(3) . . . . ?
C2 C1 C6 C7 -179.05(17) . . . . ?
C4 C5 C6 C1 0.9(3) . . . . ?
C4 C5 C6 C7 -179.41(16) . . . . ?
C24 C19 N20 C21 -0.3(3) . . . . ?
C4 C19 N20 C21 178.78(18) . . . . ?
N20 C19 C24 C23 0.5(3) . . . . ?
C4 C19 C24 C23 -178.58(19) . . . . ?
C1 C6 C7 C12 -41.1(3) . . . . ?
C5 C6 C7 C12 139.2(2) . . . . ?
C1 C6 C7 C8 139.3(2) . . . . ?
C5 C6 C7 C8 -40.4(3) . . . . ?
C4 N3 C2 O1 -178.64(16) . . . . ?
C4 N3 C2 C1 1.7(3) . . . . ?
C13 O1 C2 N3 7.0(3) . . . . ?
C13 O1 C2 C1 -173.35(18) . . . . ?
C6 C1 C2 N3 -2.1(3) . . . . ?
C6 C1 C2 O1 178.27(16) . . . . ?
C19 N20 C21 C22 0.0(3) . . . . ?
C23 C22 C21 N20 0.0(4) . . . . ?
C8 C7 C12 C11 -0.5(3) . . . . ?
C6 C7 C12 C11 179.9(2) . . . . ?
C2 O1 C13 C18 76.4(3) . . . . ?
C2 O1 C13 C14 -109.1(3) . . . . ?
C12 C7 C8 C9 1.8(3) . . . . ?
C6 C7 C8 C9 -178.6(2) . . . . ?
C7 C8 C9 C10 -1.7(4) . . . . ?
C14 C13 C18 C17 0.8(4) . . . . ?
O1 C13 C18 C17 175.1(2) . . . . ?
C21 C22 C23 C24 0.1(3) . . . . ?
C19 C24 C23 C22 -0.4(3) . . . . ?
C13 C18 C17 C16 -0.8(4) . . . . ?
C7 C12 C11 C10 -0.9(4) . . . . ?
C12 C11 C10 C9 1.0(4) . . . . ?
C8 C9 C10 C11 0.3(4) . . . . ?
C18 C13 C14 C15 -0.8(5) . . . . ?
O1 C13 C14 C15 -175.2(3) . . . . ?
C18 C17 C16 C15 0.8(5) . . . . ?
C13 C14 C15 C16 0.8(5) . . . . ?
C17 C16 C15 C14 -0.7(6) . . . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.172
_refine_diff_density_min         -0.162
_refine_diff_density_rms         0.035
