# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_xxx
_database_code_depnum_ccdc_archive 'CCDC 1922833'
loop_
_audit_author_name
_audit_author_address
'Dr. Ruchir Kant'
;CSIR CDRI, Lucknow
India
;
_audit_update_record             
;
2019-06-13 deposited with the CCDC.	2020-09-15 downloaded from the CCDC.
;

#===============================================================================

# 5. CHEMICAL DATA

_chemical_name_systematic        
;
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C27 H19 N3 O2'
# Ex: 'C12 H16 N2 O6, H2 O' and '(Cd 2+)3, (C6 N6 Cr 3-)2, 2(H2 O)'
_chemical_formula_structural     ?
_chemical_formula_sum            'C27 H19 N3 O2'
_chemical_formula_iupac          ?
_chemical_formula_weight         417.45
_chemical_compound_source        'see text'

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

#===============================================================================

# 6. CRYSTAL DATA

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_Int_Tables_number      14

loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 1/2-x,1/2+y,1/2-z
3 -x,-y,-z
4 1/2+x,1/2-y,1/2+z

_cell_length_a                   10.329(3)
_cell_length_b                   19.409(5)
_cell_length_c                   10.902(3)
_cell_angle_alpha                90
_cell_angle_beta                 98.698(5)
_cell_angle_gamma                90
_cell_volume                     2160.5(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    293
_cell_measurement_reflns_used    2496
_cell_measurement_theta_min      4.3
_cell_measurement_theta_max      25.4
_cell_special_details            
;
;

_exptl_crystal_description       Block
_exptl_crystal_colour            Colorless

_exptl_crystal_size_max          0.490
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.150
_exptl_crystal_size_rad          ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_density_method    'Not Measured'
_exptl_crystal_F_000             872
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.961
_exptl_absorpt_correction_T_max  0.988

#===============================================================================

# 7. EXPERIMENTAL DATA

_exptl_special_details           
;
;
_diffrn_ambient_temperature      293(2)
_diffrn_source_power             0.0
_diffrn_source_voltage           50.0
_diffrn_source_current           0.6
_diffrn_radiation_wavelength     0.71075
_diffrn_radiation_type           'Mo K\a'
_diffrn_source                   MicroMax003_Mo
_diffrn_radiation_monochromator  Confocal
_diffrn_measurement_specimen_support Fiber
_diffrn_detector                 CCD
_diffrn_measurement_device       
;
AFC12 (Right): Kappa 3 circle
;
_diffrn_measurement_device_type  
;
Rigaku Saturn724+ (4x4 bin mode)
;
_diffrn_detector_area_resol_mean 28.5714
_diffrn_measurement_method       'profile data from ω-scans'

_diffrn_reflns_number            13313
_diffrn_reflns_av_R_equivalents  0.1072
_diffrn_reflns_av_sigmaI/netI    0.1004
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         4.28
_diffrn_reflns_theta_max         25.38
_reflns_number_total             3718
_reflns_number_gt                2202
_reflns_threshold_expression     >2sigma(I)
_diffrn_reflns_theta_full        25.38
_diffrn_measured_fraction_theta_max 0.936
_diffrn_measured_fraction_theta_full 0.936
_computing_data_collection       
;
CrystalClear-SM Expert 2.1 b24 (Rigaku, 2012)
;
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.1 b24 (Rigaku, 2012)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.1 b24 (Rigaku, 2012)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'SHELXTL (Bruker, 1997)'
_computing_publication_material  'PLATON (Spek, 2003)'

#===============================================================================

# 8. REFINEMENT DATA

_refine_special_details          
;
 Refinement on F² for ALL reflections except those
 flagged by the user for potential systematic errors.
 Weighted R-factors wR and all goodnesses of fit S
 are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The
 observed criterion of F² > 2sigma(F²) is used only
 for calculating -R-factor-obs 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)+(0.0758P)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       0.052(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3718
_refine_ls_number_parameters     290
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0912
_refine_ls_R_factor_gt           0.0599
_refine_ls_wR_factor_ref         0.1463
_refine_ls_wR_factor_gt          0.1369
_refine_ls_goodness_of_fit_ref   0.866
_refine_ls_restrained_S_all      0.866
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.184
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.049

#===============================================================================

# 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_thermal_displace_type
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_U_iso_or_equiv
_atom_site_calc_flag
_atom_site_refinement_flags
O1 O Uani 1.1755(2) 0.20467(10) 0.53711(17) 1.000 0.0748(8) . .
O2 O Uani 0.88085(16) 0.03303(8) 0.24204(14) 1.000 0.0507(6) . .
N1 N Uani 0.85303(19) 0.14774(10) 0.20538(16) 1.000 0.0428(7) . .
N2 N Uani 1.0906(2) 0.16901(10) 0.34116(16) 1.000 0.0454(7) . .
N3 N Uani 1.3912(3) 0.10522(13) -0.2408(2) 1.000 0.0783(11) . .
C1 C Uani 0.6018(3) 0.08934(14) 0.3373(3) 1.000 0.0636(11) . .
C2 C Uani 0.5380(3) 0.09719(17) 0.4400(3) 1.000 0.0768(12) . .
C3 C Uani 0.5065(3) 0.16062(18) 0.4785(2) 1.000 0.0676(11) . .
C4 C Uani 0.5386(3) 0.21738(16) 0.4167(3) 1.000 0.0667(11) . .
C5 C Uani 0.6018(3) 0.21043(13) 0.3137(2) 1.000 0.0561(10) . .
C6 C Uani 0.6351(2) 0.14635(12) 0.2743(2) 1.000 0.0428(8) . .
C7 C Uani 0.7107(2) 0.13957(13) 0.1667(2) 1.000 0.0483(9) . .
C8 C Uani 0.9031(3) 0.21477(12) 0.2244(2) 1.000 0.0480(9) . .
C9 C Uani 1.0162(3) 0.22600(13) 0.2950(2) 1.000 0.0500(9) . .
C10 C Uani 1.1558(3) 0.15902(13) 0.4595(2) 1.000 0.0504(9) . .
C11 C Uani 1.1901(2) 0.08608(14) 0.4675(2) 1.000 0.0512(9) . .
C12 C Uani 1.1450(2) 0.05330(12) 0.36190(18) 1.000 0.0397(8) . .
C13 C Uani 1.0733(2) 0.10533(11) 0.26994(19) 1.000 0.0385(8) . .
C14 C Uani 0.9267(2) 0.09071(12) 0.23884(18) 1.000 0.0386(8) . .
C15 C Uani 1.1372(2) 0.11135(11) 0.15156(19) 1.000 0.0384(8) . .
C16 C Uani 1.2638(3) 0.13557(14) 0.1609(2) 1.000 0.0524(9) . .
C17 C Uani 1.3278(3) 0.13637(15) 0.0582(2) 1.000 0.0588(10) . .
C18 C Uani 1.2635(3) 0.11310(12) -0.0551(2) 1.000 0.0461(9) . .
C19 C Uani 1.1358(3) 0.09163(12) -0.0663(2) 1.000 0.0489(9) . .
C20 C Uani 1.0721(3) 0.09073(12) 0.03718(19) 1.000 0.0460(8) . .
C21 C Uani 1.3341(3) 0.10929(14) -0.1597(2) 1.000 0.0577(10) . .
C22 C Uani 1.1591(2) -0.02077(12) 0.33549(19) 1.000 0.0431(8) . .
C23 C Uani 1.1233(3) -0.06864(16) 0.4172(3) 1.000 0.0739(12) . .
C24 C Uani 1.1363(4) -0.13823(18) 0.3972(4) 1.000 0.0924(16) . .
C25 C Uani 1.1864(3) -0.16064(16) 0.2962(4) 1.000 0.0834(15) . .
C26 C Uani 1.2234(4) -0.11477(16) 0.2146(3) 1.000 0.0829(14) . .
C27 C Uani 1.2094(3) -0.04493(14) 0.2336(2) 1.000 0.0687(13) . .
H1 H Uiso 0.62180 0.04550 0.31120 1.000 0.0760 calc R
H2 H Uiso 0.51670 0.05840 0.48290 1.000 0.0920 calc R
H3 H Uiso 0.46310 0.16520 0.54680 1.000 0.0810 calc R
H4 H Uiso 0.51820 0.26100 0.44350 1.000 0.0800 calc R
H5 H Uiso 0.62190 0.24950 0.27090 1.000 0.0670 calc R
H7A H Uiso 0.69360 0.09470 0.12870 1.000 0.0580 calc R
H7B H Uiso 0.68030 0.17420 0.10490 1.000 0.0580 calc R
H8 H Uiso 0.85570 0.25180 0.18650 1.000 0.0580 calc R
H9 H Uiso 1.04570 0.27060 0.31370 1.000 0.0600 calc R
H11 H Uiso 1.23720 0.06510 0.53700 1.000 0.0610 calc R
H16 H Uiso 1.30650 0.15150 0.23680 1.000 0.0630 calc R
H17 H Uiso 1.41340 0.15240 0.06510 1.000 0.0710 calc R
H19 H Uiso 1.09190 0.07770 -0.14300 1.000 0.0590 calc R
H20 H Uiso 0.98540 0.07620 0.02950 1.000 0.0550 calc R
H23 H Uiso 1.08980 -0.05380 0.48720 1.000 0.0890 calc R
H24 H Uiso 1.11080 -0.16990 0.45290 1.000 0.1110 calc R
H25 H Uiso 1.19530 -0.20760 0.28300 1.000 0.1000 calc R
H26 H Uiso 1.25830 -0.13030 0.14580 1.000 0.1000 calc R
H27 H Uiso 1.23440 -0.01380 0.17670 1.000 0.0820 calc R


#===============================================================================

# 10. MOLECULAR GEOMETRY

_geom_special_details            
;
 Bond distances, angles etc. have been calculated using the
 rounded fractional coordinates. All su's are estimated
 from the variances of the (full) variance-covariance matrix.
 The cell esds are taken into account in the estimation of
 distances, angles and torsion angles
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C10 1.221(3) . . yes
O2 C14 1.218(3) . . yes
N1 C7 1.475(3) . . yes
N1 C8 1.404(3) . . yes
N1 C14 1.361(3) . . yes
N2 C9 1.397(3) . . yes
N2 C10 1.376(3) . . yes
N2 C13 1.456(3) . . yes
N3 C21 1.137(4) . . yes
C1 C2 1.391(5) . . no
C1 C6 1.373(4) . . no
C2 C3 1.356(5) . . no
C3 C4 1.358(4) . . no
C4 C5 1.388(4) . . no
C5 C6 1.376(3) . . no
C6 C7 1.510(3) . . no
C8 C9 1.316(4) . . no
C10 C11 1.459(4) . . no
C11 C12 1.336(3) . . no
C12 C13 1.533(3) . . no
C12 C22 1.478(3) . . no
C13 C14 1.527(3) . . no
C13 C15 1.540(3) . . no
C15 C16 1.379(4) . . no
C15 C20 1.383(3) . . no
C16 C17 1.384(4) . . no
C17 C18 1.387(3) . . no
C18 C19 1.371(4) . . no
C18 C21 1.445(4) . . no
C19 C20 1.389(4) . . no
C22 C23 1.376(4) . . no
C22 C27 1.378(3) . . no
C23 C24 1.378(5) . . no
C24 C25 1.357(6) . . no
C25 C26 1.354(5) . . no
C26 C27 1.382(4) . . no
C1 H1 0.9300 . . no
C2 H2 0.9300 . . no
C3 H3 0.9300 . . no
C4 H4 0.9300 . . no
C5 H5 0.9300 . . no
C7 H7A 0.9700 . . no
C7 H7B 0.9700 . . no
C8 H8 0.9300 . . no
C9 H9 0.9300 . . no
C11 H11 0.9300 . . no
C16 H16 0.9300 . . no
C17 H17 0.9300 . . no
C19 H19 0.9300 . . no
C20 H20 0.9300 . . no
C23 H23 0.9300 . . no
C24 H24 0.9300 . . no
C25 H25 0.9300 . . no
C26 H26 0.9300 . . no
C27 H27 0.9300 . . no

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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 N1 C8 118.1(2) . . . yes
C7 N1 C14 118.79(19) . . . yes
C8 N1 C14 122.4(2) . . . yes
C9 N2 C10 127.9(2) . . . yes
C9 N2 C13 117.62(18) . . . yes
C10 N2 C13 112.56(19) . . . yes
C2 C1 C6 120.0(3) . . . no
C1 C2 C3 120.9(3) . . . no
C2 C3 C4 119.7(3) . . . no
C3 C4 C5 120.2(3) . . . no
C4 C5 C6 120.7(2) . . . no
C1 C6 C5 118.6(2) . . . no
C1 C6 C7 121.1(2) . . . no
C5 C6 C7 120.3(2) . . . no
N1 C7 C6 112.25(17) . . . yes
N1 C8 C9 121.0(2) . . . yes
N2 C9 C8 118.1(2) . . . yes
O1 C10 N2 123.7(2) . . . yes
O1 C10 C11 130.5(2) . . . yes
N2 C10 C11 105.83(19) . . . yes
C10 C11 C12 111.2(2) . . . no
C11 C12 C13 108.7(2) . . . no
C11 C12 C22 126.8(2) . . . no
C13 C12 C22 124.45(18) . . . no
N2 C13 C12 101.67(16) . . . yes
N2 C13 C14 108.28(18) . . . yes
N2 C13 C15 110.41(17) . . . yes
C12 C13 C14 112.80(17) . . . no
C12 C13 C15 111.85(17) . . . no
C14 C13 C15 111.35(17) . . . no
O2 C14 N1 123.4(2) . . . yes
O2 C14 C13 122.8(2) . . . yes
N1 C14 C13 113.80(19) . . . yes
C13 C15 C16 119.06(18) . . . no
C13 C15 C20 121.5(2) . . . no
C16 C15 C20 119.4(2) . . . no
C15 C16 C17 120.5(2) . . . no
C16 C17 C18 119.6(3) . . . no
C17 C18 C19 120.2(2) . . . no
C17 C18 C21 119.3(3) . . . no
C19 C18 C21 120.5(2) . . . no
C18 C19 C20 119.9(2) . . . no
C15 C20 C19 120.2(3) . . . no
N3 C21 C18 178.6(3) . . . yes
C12 C22 C23 119.1(2) . . . no
C12 C22 C27 123.3(2) . . . no
C23 C22 C27 117.6(2) . . . no
C22 C23 C24 121.2(3) . . . no
C23 C24 C25 120.1(3) . . . no
C24 C25 C26 120.2(3) . . . no
C25 C26 C27 120.0(3) . . . no
C22 C27 C26 121.0(3) . . . no
C2 C1 H1 120.00 . . . no
C6 C1 H1 120.00 . . . no
C1 C2 H2 120.00 . . . no
C3 C2 H2 120.00 . . . no
C2 C3 H3 120.00 . . . no
C4 C3 H3 120.00 . . . no
C3 C4 H4 120.00 . . . no
C5 C4 H4 120.00 . . . no
C4 C5 H5 120.00 . . . no
C6 C5 H5 120.00 . . . no
N1 C7 H7A 109.00 . . . no
N1 C7 H7B 109.00 . . . no
C6 C7 H7A 109.00 . . . no
C6 C7 H7B 109.00 . . . no
H7A C7 H7B 108.00 . . . no
N1 C8 H8 120.00 . . . no
C9 C8 H8 120.00 . . . no
N2 C9 H9 121.00 . . . no
C8 C9 H9 121.00 . . . no
C10 C11 H11 124.00 . . . no
C12 C11 H11 124.00 . . . no
C15 C16 H16 120.00 . . . no
C17 C16 H16 120.00 . . . no
C16 C17 H17 120.00 . . . no
C18 C17 H17 120.00 . . . no
C18 C19 H19 120.00 . . . no
C20 C19 H19 120.00 . . . no
C15 C20 H20 120.00 . . . no
C19 C20 H20 120.00 . . . no
C22 C23 H23 119.00 . . . no
C24 C23 H23 119.00 . . . no
C23 C24 H24 120.00 . . . no
C25 C24 H24 120.00 . . . no
C24 C25 H25 120.00 . . . no
C26 C25 H25 120.00 . . . no
C25 C26 H26 120.00 . . . no
C27 C26 H26 120.00 . . . no
C22 C27 H27 120.00 . . . no
C26 C27 H27 119.00 . . . no

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 C14 O2 -2.2(3) . . . . no
C8 N1 C14 O2 167.7(2) . . . . no
C7 N1 C14 C13 176.76(17) . . . . no
C8 N1 C7 C6 -79.3(2) . . . . no
C14 N1 C7 C6 91.0(2) . . . . no
C7 N1 C8 C9 157.8(2) . . . . no
C14 N1 C8 C9 -12.1(3) . . . . no
C8 N1 C14 C13 -13.4(3) . . . . no
C10 N2 C9 C8 -136.0(3) . . . . no
C9 N2 C10 O1 -12.8(5) . . . . no
C13 N2 C10 O1 -176.4(3) . . . . no
C13 N2 C9 C8 26.9(3) . . . . no
C10 N2 C13 C12 -2.6(2) . . . . no
C9 N2 C13 C14 -49.1(3) . . . . no
C10 N2 C13 C15 -121.5(2) . . . . no
C10 N2 C13 C14 116.4(2) . . . . no
C9 N2 C13 C15 73.1(3) . . . . no
C13 N2 C10 C11 2.8(3) . . . . no
C9 N2 C13 C12 -168.1(2) . . . . no
C9 N2 C10 C11 166.4(2) . . . . no
C2 C1 C6 C5 -1.2(4) . . . . no
C2 C1 C6 C7 176.7(3) . . . . no
C6 C1 C2 C3 0.8(5) . . . . no
C1 C2 C3 C4 -0.6(5) . . . . no
C2 C3 C4 C5 0.8(5) . . . . no
C3 C4 C5 C6 -1.3(4) . . . . no
C4 C5 C6 C1 1.5(4) . . . . no
C4 C5 C6 C7 -176.5(2) . . . . no
C5 C6 C7 N1 83.4(3) . . . . no
C1 C6 C7 N1 -94.5(3) . . . . no
N1 C8 C9 N2 5.8(4) . . . . no
N2 C10 C11 C12 -1.8(3) . . . . no
O1 C10 C11 C12 177.3(3) . . . . no
C10 C11 C12 C22 -179.3(2) . . . . no
C10 C11 C12 C13 0.2(3) . . . . no
C11 C12 C13 C15 119.2(2) . . . . no
C22 C12 C13 N2 -179.13(19) . . . . no
C22 C12 C13 C15 -61.3(3) . . . . no
C11 C12 C22 C23 51.5(3) . . . . no
C22 C12 C13 C14 65.1(3) . . . . no
C11 C12 C13 C14 -114.4(2) . . . . no
C13 C12 C22 C27 53.6(3) . . . . no
C11 C12 C13 N2 1.4(2) . . . . no
C11 C12 C22 C27 -127.0(3) . . . . no
C13 C12 C22 C23 -127.9(2) . . . . no
N2 C13 C14 N1 41.0(2) . . . . no
C12 C13 C14 O2 -28.3(3) . . . . no
C12 C13 C14 N1 152.75(18) . . . . no
C15 C13 C14 O2 98.4(2) . . . . no
C12 C13 C15 C16 -63.4(3) . . . . no
C12 C13 C15 C20 114.3(2) . . . . no
C14 C13 C15 C16 169.4(2) . . . . no
C14 C13 C15 C20 -12.9(3) . . . . no
C15 C13 C14 N1 -80.5(2) . . . . no
N2 C13 C15 C16 49.1(3) . . . . no
N2 C13 C15 C20 -133.3(2) . . . . no
N2 C13 C14 O2 -140.0(2) . . . . no
C13 C15 C16 C17 174.7(2) . . . . no
C20 C15 C16 C17 -3.0(4) . . . . no
C13 C15 C20 C19 -174.9(2) . . . . no
C16 C15 C20 C19 2.8(4) . . . . no
C15 C16 C17 C18 0.5(4) . . . . no
C16 C17 C18 C19 2.2(4) . . . . no
C16 C17 C18 C21 -175.4(3) . . . . no
C17 C18 C19 C20 -2.4(4) . . . . no
C21 C18 C19 C20 175.2(2) . . . . no
C18 C19 C20 C15 -0.1(4) . . . . no
C12 C22 C23 C24 -179.2(3) . . . . no
C27 C22 C23 C24 -0.5(4) . . . . no
C12 C22 C27 C26 178.5(3) . . . . no
C23 C22 C27 C26 -0.1(4) . . . . no
C22 C23 C24 C25 0.7(6) . . . . no
C23 C24 C25 C26 -0.2(6) . . . . no
C24 C25 C26 C27 -0.4(6) . . . . no
C25 C26 C27 C22 0.6(5) . . . . no

loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_1
_geom_contact_site_symmetry_2
_geom_contact_publ_flag
O1 C7 3.334(3) . 4_555 no
O1 C8 3.269(3) . 4_555 no
O2 C6 3.417(3) . . no
O2 C1 3.389(4) . . no
O2 C19 3.075(3) . 3_755 no
O2 C20 3.388(3) . . no
O2 C22 3.083(3) . . no
O1 H7B 2.4600 . 4_555 no
O1 H8 2.4300 . 4_555 no
O1 H5 2.8300 . 4_555 no
O1 H9 2.8900 . . no
O2 H7A 2.4400 . . no
O2 H20 2.8300 . . no
O2 H1 2.9000 . . no
O2 H19 2.4400 . 3_755 no
N1 N2 2.699(3) . . no
N1 C20 3.311(3) . . no
N2 N1 2.699(3) . . no
N1 H20 2.8800 . . no
N2 H16 2.6700 . . no
N3 H3 2.7900 . 1_654 no
N3 H11 2.8000 . 1_554 no
N3 H8 2.8900 . 4_554 no
N3 H9 2.9000 . 4_554 no
C1 O2 3.389(4) . . no
C3 C10 3.597(5) . 1_455 no
C3 C11 3.559(4) . 1_455 no
C5 C8 3.400(4) . . no
C6 O2 3.417(3) . . no
C7 O1 3.334(3) . 4_454 no
C8 C15 3.330(4) . . no
C8 C5 3.400(4) . . no
C8 O1 3.269(3) . 4_454 no
C9 C16 3.590(4) . . no
C10 C3 3.597(5) . 1_655 no
C11 C3 3.559(4) . 1_655 no
C15 C27 3.218(4) . . no
C15 C8 3.330(4) . . no
C16 C9 3.590(4) . . no
C19 O2 3.075(3) . 3_755 no
C20 C27 3.551(4) . . no
C20 O2 3.388(3) . . no
C20 N1 3.311(3) . . no
C22 O2 3.083(3) . . no
C27 C15 3.218(4) . . no
C27 C20 3.551(4) . . no
C3 H16 3.1000 . 1_455 no
C6 H17 2.9800 . 1_455 no
C8 H5 3.1000 . . no
C10 H24 3.0600 . 3_756 no
C10 H16 3.0800 . . no
C11 H23 3.0700 . 3_756 no
C11 H23 2.9300 . . no
C12 H16 2.9900 . . no
C14 H20 2.4600 . . no
C15 H27 2.6300 . . no
C16 H27 2.9200 . . no
C20 H27 2.9100 . . no
C20 H4 3.0800 . 4_554 no
C23 H11 3.0600 . . no
H1 O2 2.9000 . . no
H1 H7A 2.4200 . . no
H2 H2 2.3300 . 3_656 no
H3 N3 2.7900 . 1_456 no
H3 H8 2.5800 . 4_455 no
H4 C20 3.0800 . 4_455 no
H5 C8 3.1000 . . no
H5 H7B 2.4700 . . no
H5 O1 2.8300 . 4_454 no
H7A O2 2.4400 . . no
H7A H1 2.4200 . . no
H7B H5 2.4700 . . no
H7B H8 2.4200 . . no
H7B O1 2.4600 . 4_454 no
H8 H7B 2.4200 . . no
H8 O1 2.4300 . 4_454 no
H8 N3 2.8900 . 4_455 no
H8 H3 2.5800 . 4_554 no
H9 O1 2.8900 . . no
H9 N3 2.9000 . 4_455 no
H11 N3 2.8000 . 1_556 no
H11 C23 3.0600 . . no
H16 N2 2.6700 . . no
H16 C3 3.1000 . 1_655 no
H16 C10 3.0800 . . no
H16 C12 2.9900 . . no
H17 C6 2.9800 . 1_655 no
H19 O2 2.4400 . 3_755 no
H20 O2 2.8300 . . no
H20 N1 2.8800 . . no
H20 C14 2.4600 . . no
H23 C11 2.9300 . . no
H23 C11 3.0700 . 3_756 no
H24 C10 3.0600 . 3_756 no
H27 C15 2.6300 . . no
H27 C16 2.9200 . . no
H27 C20 2.9100 . . no

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
_geom_hbond_publ_flag
#
#D   H   A   D - H  H...A   D...A    D - H...A  symm(A)
#
C7 H7B O1 0.9700 2.4600 3.334(3) 149.00 4_454 yes
C8 H8 O1 0.9300 2.4300 3.269(3) 150.00 4_454 yes
C19 H19 O2 0.9300 2.4400 3.075(3) 126.00 3_755 yes


####################################################################
#                         END of data
####################################################################

####################################################################### 
# 
# 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_KA770_0m
_database_code_depnum_ccdc_archive 'CCDC 1944108'
loop_
_audit_author_name
_audit_author_address
'Jagadeesh Babu Nanubolu'
;CSIR Indian Institute of Chemical Technology
India
;
_audit_update_record             
;
2019-07-30 deposited with the CCDC.	2020-09-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        
(E)-4-benzyl-7-benzylidene-6-(4-fluorophenyl)-1,4-diazabicyclo[4.2.0]oct-2-ene-5,8-dione
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H19 F N2 O2'
_chemical_formula_sum            'C26 H19 F N2 O2'
_chemical_formula_weight         410.43

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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'

_cell_length_a                   9.0888(9)
_cell_length_b                   10.5640(11)
_cell_length_c                   21.4630(19)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2060.8(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    9929
_cell_measurement_theta_min      2.433
_cell_measurement_theta_max      26.544

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_F_000             856
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.380
_exptl_crystal_size_min          0.320
_exptl_absorpt_coefficient_mu    0.091
_shelx_estimated_absorpt_T_min   0.965
_shelx_estimated_absorpt_T_max   0.972
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6793
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   microfocus
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON-100'
_diffrn_measurement_method       'ω and φ'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13121
_diffrn_reflns_av_unetI/netI     0.0222
_diffrn_reflns_av_R_equivalents  0.0213
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.434
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_full        24.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             3623
_reflns_number_gt                3266
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.735
_reflns_Friedel_fraction_max     0.994
_reflns_Friedel_fraction_full    0.994

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.043(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 1280 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(2)
_chemical_absolute_configuration syn
_refine_ls_number_reflns         3623
_refine_ls_number_parameters     281
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0459
_refine_ls_R_factor_gt           0.0410
_refine_ls_wR_factor_ref         0.1365
_refine_ls_wR_factor_gt          0.1305
_refine_ls_goodness_of_fit_ref   1.149
_refine_ls_restrained_S_all      1.149
_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_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
C1 C 0.6618(4) 1.0231(3) 0.31271(14) 0.0790(9) Uani 1 1 d . . . . .
C2 C 0.6560(6) 1.1528(4) 0.31631(17) 0.1022(13) Uani 1 1 d . . . . .
H2 H 0.594939 1.197380 0.289325 0.123 Uiso 1 1 calc R U . . .
C3 C 0.7393(7) 1.2180(5) 0.3593(2) 0.1170(15) Uani 1 1 d . . . . .
H3 H 0.735353 1.305910 0.360555 0.140 Uiso 1 1 calc R U . . .
C4 C 0.8272(6) 1.1545(6) 0.3998(2) 0.1209(16) Uani 1 1 d . . . . .
H4 H 0.884137 1.198488 0.428537 0.145 Uiso 1 1 calc R U . . .
C5 C 0.8310(6) 1.0254(7) 0.3977(4) 0.142(2) Uani 1 1 d . . . . .
H5 H 0.889390 0.981081 0.425845 0.171 Uiso 1 1 calc R U . . .
C6 C 0.7499(5) 0.9610(5) 0.3547(3) 0.1149(16) Uani 1 1 d . . . . .
H6 H 0.754268 0.873059 0.353861 0.138 Uiso 1 1 calc R U . . .
C7 C 0.5681(5) 0.9535(4) 0.26512(14) 0.0991(13) Uani 1 1 d . . . . .
H7A H 0.561095 1.004287 0.227575 0.119 Uiso 1 1 calc R U . . .
H7AB H 0.615760 0.874368 0.254285 0.119 Uiso 1 1 calc R U . . .
C8 C 0.3973(3) 0.8184(3) 0.32200(11) 0.0597(7) Uani 1 1 d . . . . .
C9 C 0.2489(3) 0.8066(2) 0.35459(11) 0.0546(6) Uani 1 1 d . . . . .
C10 C 0.1708(6) 0.9982(3) 0.29233(15) 0.0864(12) Uani 1 1 d . . . . .
H10 H 0.098773 1.058203 0.283644 0.104 Uiso 1 1 calc R U . . .
C11 C 0.3108(6) 1.0183(3) 0.27855(15) 0.0864(11) Uani 1 1 d . . . . .
H11 H 0.337762 1.096031 0.261717 0.104 Uiso 1 1 calc R U . . .
C12 C 0.1548(3) 0.6910(3) 0.33559(11) 0.0588(6) Uani 1 1 d . . . . .
C13 C 0.0584(4) 0.7775(3) 0.29955(14) 0.0715(8) Uani 1 1 d . . . . .
C14 C 0.1451(3) 0.5656(3) 0.34219(11) 0.0594(6) Uani 1 1 d . . . . .
H14 H 0.067533 0.529652 0.320125 0.071 Uiso 1 1 calc R U . . .
C15 C 0.2316(3) 0.4743(2) 0.37701(12) 0.0577(6) Uani 1 1 d . . . . .
C16 C 0.3603(4) 0.5047(3) 0.40849(15) 0.0682(7) Uani 1 1 d . . . . .
H16 H 0.392317 0.588262 0.409874 0.082 Uiso 1 1 calc R U . . .
C17 C 0.4402(5) 0.4118(3) 0.43754(17) 0.0861(10) Uani 1 1 d . . . . .
H17 H 0.527819 0.432744 0.457371 0.103 Uiso 1 1 calc R U . . .
C18 C 0.3930(6) 0.2887(3) 0.43782(19) 0.0997(13) Uani 1 1 d . . . . .
H18 H 0.448399 0.226371 0.457424 0.120 Uiso 1 1 calc R U . . .
C19 C 0.2625(6) 0.2582(3) 0.4088(2) 0.1023(13) Uani 1 1 d . . . . .
H19 H 0.227853 0.175418 0.410282 0.123 Uiso 1 1 calc R U . . .
C20 C 0.1835(5) 0.3486(3) 0.37766(15) 0.0819(10) Uani 1 1 d . . . . .
H20 H 0.097566 0.326342 0.356880 0.098 Uiso 1 1 calc R U . . .
C21 C 0.2631(3) 0.8384(2) 0.42323(10) 0.0484(5) Uani 1 1 d . . . . .
C22 C 0.3694(3) 0.9228(2) 0.44371(11) 0.0553(6) Uani 1 1 d . . . . .
H22 H 0.433742 0.958984 0.415128 0.066 Uiso 1 1 calc R U . . .
C23 C 0.3810(3) 0.9541(3) 0.50672(13) 0.0625(7) Uani 1 1 d . . . . .
H23 H 0.451946 1.011131 0.520364 0.075 Uiso 1 1 calc R U . . .
C24 C 0.2863(3) 0.8994(3) 0.54770(12) 0.0640(7) Uani 1 1 d . . . . .
C25 C 0.1809(3) 0.8155(3) 0.52974(13) 0.0702(8) Uani 1 1 d . . . . .
H25 H 0.118091 0.779035 0.558852 0.084 Uiso 1 1 calc R U . . .
C26 C 0.1693(3) 0.7857(3) 0.46668(13) 0.0645(7) Uani 1 1 d . . . . .
H26 H 0.097109 0.729183 0.453631 0.077 Uiso 1 1 calc R U . . .
N1 N 0.4195(4) 0.9270(2) 0.28838(10) 0.0749(8) Uani 1 1 d . . . . .
N2 N 0.1361(3) 0.8821(2) 0.32071(12) 0.0722(7) Uani 1 1 d . . . . .
O1 O 0.4926(2) 0.7374(2) 0.32835(9) 0.0694(6) Uani 1 1 d . . . . .
O2 O -0.0438(3) 0.7683(3) 0.26436(12) 0.0930(8) Uani 1 1 d . . . . .
F1 F 0.2972(3) 0.9313(3) 0.60825(8) 0.1000(7) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.373(6) . ?
C1 C2 1.374(5) . ?
C1 C7 1.519(5) . ?
C2 C3 1.377(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.357(8) . ?
C3 H3 0.9300 . ?
C4 C5 1.365(9) . ?
C4 H4 0.9300 . ?
C5 C6 1.363(9) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 N1 1.467(5) . ?
C7 H7A 0.9700 . ?
C7 H7AB 0.9700 . ?
C8 O1 1.226(4) . ?
C8 N1 1.370(3) . ?
C8 C9 1.524(4) . ?
C9 N2 1.489(3) . ?
C9 C21 1.516(3) . ?
C9 C12 1.546(4) . ?
C10 C11 1.323(6) . ?
C10 N2 1.406(4) . ?
C10 H10 0.9300 . ?
C11 N1 1.397(5) . ?
C11 H11 0.9300 . ?
C12 C14 1.336(4) . ?
C12 C13 1.483(4) . ?
C13 O2 1.201(4) . ?
C13 N2 1.388(4) . ?
C14 C15 1.452(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.388(4) . ?
C15 C20 1.398(4) . ?
C16 C17 1.371(5) . ?
C16 H16 0.9300 . ?
C17 C18 1.369(6) . ?
C17 H17 0.9300 . ?
C18 C19 1.378(7) . ?
C18 H18 0.9300 . ?
C19 C20 1.369(6) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C21 C26 1.381(4) . ?
C21 C22 1.386(4) . ?
C22 C23 1.396(4) . ?
C22 H22 0.9300 . ?
C23 C24 1.359(4) . ?
C23 H23 0.9300 . ?
C24 F1 1.346(3) . ?
C24 C25 1.360(4) . ?
C25 C26 1.394(4) . ?
C25 H25 0.9300 . ?
C26 H26 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 117.5(4) . . ?
C6 C1 C7 122.5(4) . . ?
C2 C1 C7 119.9(4) . . ?
C1 C2 C3 121.0(5) . . ?
C1 C2 H2 119.5 . . ?
C3 C2 H2 119.5 . . ?
C4 C3 C2 120.4(5) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C3 C4 C5 119.2(5) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 H4 120.4 . . ?
C6 C5 C4 120.4(6) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C5 C6 C1 121.5(5) . . ?
C5 C6 H6 119.3 . . ?
C1 C6 H6 119.3 . . ?
N1 C7 C1 112.3(3) . . ?
N1 C7 H7A 109.1 . . ?
C1 C7 H7A 109.1 . . ?
N1 C7 H7AB 109.1 . . ?
C1 C7 H7AB 109.1 . . ?
H7A C7 H7AB 107.9 . . ?
O1 C8 N1 122.6(3) . . ?
O1 C8 C9 121.1(2) . . ?
N1 C8 C9 116.1(3) . . ?
N2 C9 C21 114.5(2) . . ?
N2 C9 C8 110.0(2) . . ?
C21 C9 C8 110.6(2) . . ?
N2 C9 C12 84.98(19) . . ?
C21 C9 C12 118.6(2) . . ?
C8 C9 C12 115.7(2) . . ?
C11 C10 N2 116.9(3) . . ?
C11 C10 H10 121.5 . . ?
N2 C10 H10 121.5 . . ?
C10 C11 N1 122.4(3) . . ?
C10 C11 H11 118.8 . . ?
N1 C11 H11 118.8 . . ?
C14 C12 C13 128.8(2) . . ?
C14 C12 C9 142.4(2) . . ?
C13 C12 C9 88.8(2) . . ?
O2 C13 N2 131.5(3) . . ?
O2 C13 C12 137.4(3) . . ?
N2 C13 C12 91.1(2) . . ?
C12 C14 C15 132.7(3) . . ?
C12 C14 H14 113.7 . . ?
C15 C14 H14 113.7 . . ?
C16 C15 C20 118.6(3) . . ?
C16 C15 C14 123.6(2) . . ?
C20 C15 C14 117.8(3) . . ?
C17 C16 C15 120.1(3) . . ?
C17 C16 H16 119.9 . . ?
C15 C16 H16 119.9 . . ?
C18 C17 C16 121.1(4) . . ?
C18 C17 H17 119.5 . . ?
C16 C17 H17 119.5 . . ?
C17 C18 C19 119.3(4) . . ?
C17 C18 H18 120.3 . . ?
C19 C18 H18 120.3 . . ?
C20 C19 C18 120.6(3) . . ?
C20 C19 H19 119.7 . . ?
C18 C19 H19 119.7 . . ?
C19 C20 C15 120.3(4) . . ?
C19 C20 H20 119.9 . . ?
C15 C20 H20 119.9 . . ?
C26 C21 C22 118.4(2) . . ?
C26 C21 C9 120.9(2) . . ?
C22 C21 C9 120.7(2) . . ?
C21 C22 C23 120.8(2) . . ?
C21 C22 H22 119.6 . . ?
C23 C22 H22 119.6 . . ?
C24 C23 C22 118.6(3) . . ?
C24 C23 H23 120.7 . . ?
C22 C23 H23 120.7 . . ?
F1 C24 C23 118.1(3) . . ?
F1 C24 C25 119.2(3) . . ?
C23 C24 C25 122.6(3) . . ?
C24 C25 C26 118.4(3) . . ?
C24 C25 H25 120.8 . . ?
C26 C25 H25 120.8 . . ?
C21 C26 C25 121.2(3) . . ?
C21 C26 H26 119.4 . . ?
C25 C26 H26 119.4 . . ?
C8 N1 C11 123.6(3) . . ?
C8 N1 C7 118.4(3) . . ?
C11 N1 C7 117.9(3) . . ?
C13 N2 C10 131.9(2) . . ?
C13 N2 C9 94.8(2) . . ?
C10 N2 C9 121.6(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 2.0(7) . . . . ?
C7 C1 C2 C3 179.7(4) . . . . ?
C1 C2 C3 C4 -1.1(8) . . . . ?
C2 C3 C4 C5 -0.6(9) . . . . ?
C3 C4 C5 C6 1.3(11) . . . . ?
C4 C5 C6 C1 -0.4(10) . . . . ?
C2 C1 C6 C5 -1.3(7) . . . . ?
C7 C1 C6 C5 -178.9(5) . . . . ?
C6 C1 C7 N1 91.3(5) . . . . ?
C2 C1 C7 N1 -86.2(4) . . . . ?
O1 C8 C9 N2 -156.7(2) . . . . ?
N1 C8 C9 N2 26.6(3) . . . . ?
O1 C8 C9 C21 75.9(3) . . . . ?
N1 C8 C9 C21 -100.9(2) . . . . ?
O1 C8 C9 C12 -62.6(3) . . . . ?
N1 C8 C9 C12 120.7(2) . . . . ?
N2 C10 C11 N1 3.3(5) . . . . ?
N2 C9 C12 C14 -176.6(4) . . . . ?
C21 C9 C12 C14 -61.4(5) . . . . ?
C8 C9 C12 C14 73.6(5) . . . . ?
N2 C9 C12 C13 4.2(2) . . . . ?
C21 C9 C12 C13 119.4(3) . . . . ?
C8 C9 C12 C13 -105.6(2) . . . . ?
C14 C12 C13 O2 -5.7(7) . . . . ?
C9 C12 C13 O2 173.7(4) . . . . ?
C14 C12 C13 N2 176.1(3) . . . . ?
C9 C12 C13 N2 -4.5(2) . . . . ?
C13 C12 C14 C15 -178.7(3) . . . . ?
C9 C12 C14 C15 2.3(7) . . . . ?
C12 C14 C15 C16 -6.2(5) . . . . ?
C12 C14 C15 C20 175.0(3) . . . . ?
C20 C15 C16 C17 2.3(5) . . . . ?
C14 C15 C16 C17 -176.5(3) . . . . ?
C15 C16 C17 C18 -2.0(6) . . . . ?
C16 C17 C18 C19 -0.4(7) . . . . ?
C17 C18 C19 C20 2.7(7) . . . . ?
C18 C19 C20 C15 -2.4(7) . . . . ?
C16 C15 C20 C19 -0.1(5) . . . . ?
C14 C15 C20 C19 178.7(4) . . . . ?
N2 C9 C21 C26 83.2(3) . . . . ?
C8 C9 C21 C26 -151.9(2) . . . . ?
C12 C9 C21 C26 -14.8(4) . . . . ?
N2 C9 C21 C22 -95.9(3) . . . . ?
C8 C9 C21 C22 29.1(3) . . . . ?
C12 C9 C21 C22 166.2(2) . . . . ?
C26 C21 C22 C23 -0.3(4) . . . . ?
C9 C21 C22 C23 178.8(2) . . . . ?
C21 C22 C23 C24 0.4(4) . . . . ?
C22 C23 C24 F1 -179.2(3) . . . . ?
C22 C23 C24 C25 0.0(4) . . . . ?
F1 C24 C25 C26 178.6(3) . . . . ?
C23 C24 C25 C26 -0.5(5) . . . . ?
C22 C21 C26 C25 -0.3(4) . . . . ?
C9 C21 C26 C25 -179.4(3) . . . . ?
C24 C25 C26 C21 0.7(5) . . . . ?
O1 C8 N1 C11 177.5(3) . . . . ?
C9 C8 N1 C11 -5.9(4) . . . . ?
O1 C8 N1 C7 -7.0(4) . . . . ?
C9 C8 N1 C7 169.6(2) . . . . ?
C10 C11 N1 C8 -11.2(5) . . . . ?
C10 C11 N1 C7 173.3(3) . . . . ?
C1 C7 N1 C8 -86.7(4) . . . . ?
C1 C7 N1 C11 89.0(4) . . . . ?
O2 C13 N2 C10 -32.3(7) . . . . ?
C12 C13 N2 C10 146.1(4) . . . . ?
O2 C13 N2 C9 -173.7(4) . . . . ?
C12 C13 N2 C9 4.7(3) . . . . ?
C11 C10 N2 C13 -111.3(4) . . . . ?
C11 C10 N2 C9 21.9(4) . . . . ?
C21 C9 N2 C13 -123.7(3) . . . . ?
C8 C9 N2 C13 111.0(3) . . . . ?
C12 C9 N2 C13 -4.5(2) . . . . ?
C21 C9 N2 C10 89.3(3) . . . . ?
C8 C9 N2 C10 -36.0(3) . . . . ?
C12 C9 N2 C10 -151.5(3) . . . . ?

_refine_diff_density_max         0.221
_refine_diff_density_min         -0.158
_refine_diff_density_rms         0.050


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Methanol'
