# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_dbr0415-5-2019
_database_code_depnum_ccdc_archive 'CCDC 1936272'
loop_
_audit_author_name
_audit_author_address
'Dr. Raghavaiah Pallepogu'
;Assistant Professor
India
;
_audit_update_record             
;
2019-06-25 deposited with the CCDC.	2019-08-19 downloaded from the CCDC.
;
_audit_creation_date             2019-06-04
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '0.67(C18 H14 Cl N3)'
_chemical_formula_sum            'C12 H9.33 Cl0.67 N2'
_chemical_formula_weight         205.18
_chemical_melting_point          ?
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'
Cl Cl 0.1484 0.1585 '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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   14.4450(9)
_cell_length_b                   6.6377(3)
_cell_length_c                   15.6545(6)
_cell_angle_alpha                90
_cell_angle_beta                 94.414(5)
_cell_angle_gamma                90
_cell_volume                     1496.53(13)
_cell_formula_units_Z            6
_cell_measurement_reflns_used    4124
_cell_measurement_temperature    297.4(6)
_cell_measurement_theta_max      25.7740
_cell_measurement_theta_min      2.6040
_shelx_estimated_absorpt_T_max   0.970
_shelx_estimated_absorpt_T_min   0.951
_exptl_absorpt_coefficient_mu    0.255
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.55190
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.35a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.366
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             640
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0804
_diffrn_reflns_av_unetI/netI     0.0505
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            11729
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.022
_diffrn_reflns_theta_min         1.996
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      297.4(6)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix3000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -21.00   9.00   0.50   10.63    --  -14.97 -79.00  44.00   60
  2  ω    -35.00  22.00   0.50   10.63    --  -14.97 -94.00  30.00  114
  3  ω    -48.00 -20.00   0.50   10.63    --   16.22 -79.00  44.00   56
  4  ω    -55.00  38.00   0.50   10.63    --   16.22 -30.00  30.00  186
  5  ω    -65.00 -39.00   0.50   10.63    --  -14.97 -79.00  44.00   52
  6  ω    -29.00  20.00   0.50   10.63    --  -14.97 -94.00 150.00   98
  7  ω     -5.00  35.00   0.50   10.63    --   16.22  79.00 168.00   80
  8  ω     39.00  71.00   0.50   10.63    --   16.22  79.00 168.00   64
  9  ω     22.00  49.00   0.50   10.63    --  -14.97  79.00 168.00   54
 10  ω    -54.00 -29.00   0.50   10.63    --  -14.97 125.00  90.00   50
 11  ω    -24.00  15.00   0.50   10.63    --  -14.97 -94.00 -90.00   78
 12  ω     11.00  44.00   0.50   10.63    --   16.22-125.00-120.00   66
 13  ω    -22.00  23.00   0.50   10.63    --   16.22 -45.00-150.00   90
 14  ω     -2.00  82.00   0.50   10.63    --   16.22  45.00 -90.00  168
 15  ω    -52.00 -27.00   0.50   10.63    --   16.22 -45.00-150.00   50
 16  ω    -64.00 -31.00   0.50   10.63    --  -14.97 125.00-180.00   66
 17  ω    -61.00 -31.00   0.50   10.63    --  -14.97 125.00-150.00   60
 18  ω    -52.00 -12.00   0.50   10.63    --  -14.97 125.00-120.00   80
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at offset/far, HyPix3000'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0317445000
_diffrn_orient_matrix_UB_12      -0.0271511000
_diffrn_orient_matrix_UB_13      0.0304566000
_diffrn_orient_matrix_UB_21      -0.0268237000
_diffrn_orient_matrix_UB_22      0.0870331000
_diffrn_orient_matrix_UB_23      -0.0109378000
_diffrn_orient_matrix_UB_31      -0.0264935000
_diffrn_orient_matrix_UB_32      -0.0557216000
_diffrn_orient_matrix_UB_33      -0.0318603000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1601
_reflns_number_total             2641
_reflns_odcompleteness_completeness 99.58
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.35a (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.398
_refine_diff_density_min         -0.282
_refine_diff_density_rms         0.071
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2641
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1144
_refine_ls_R_factor_gt           0.0775
_refine_ls_restrained_S_all      1.046
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1662P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2213
_refine_ls_wR_factor_ref         0.2595
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C00I(H00C,H00F), C00L(H00I,H00L)
2.b Aromatic/amide H refined with riding coordinates:
 C009(H009), C00A(H00A), C00B(H00B), C00D(H00D), C00E(H00E), C00G(H00G),
 C00H(H00H), C00J(H00J), C00K(H00K), C00M(H00M)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
Cl1 Cl 0.62423(10) 1.0832(2) 0.91076(7) 0.0962(6) Uani 1 1 d . . . . .
N002 N 0.6239(2) 0.5793(4) 0.60040(17) 0.0536(8) Uani 1 1 d . . . . .
N003 N 0.6097(2) 0.3766(4) 0.6111(2) 0.0687(10) Uani 1 1 d . . . . .
N004 N 0.6063(2) 0.2945(4) 0.5355(2) 0.0720(10) Uani 1 1 d . . . . .
C005 C 0.6293(2) 0.6207(5) 0.5171(2) 0.0541(9) Uani 1 1 d . . . . .
C006 C 0.6316(2) 0.5806(5) 0.3356(2) 0.0540(9) Uani 1 1 d . . . . .
C007 C 0.6267(2) 0.7037(5) 0.6744(2) 0.0552(9) Uani 1 1 d . . . . .
C008 C 0.6185(3) 0.4395(5) 0.4759(2) 0.0574(10) Uani 1 1 d . . . . .
C009 C 0.6175(3) 0.4204(5) 0.3848(2) 0.0620(10) Uani 1 1 d . . . . .
H009 H 0.6070 0.2949 0.3595 0.074 Uiso 1 1 calc R . . . .
C00A C 0.6628(3) 0.6290(6) 0.7521(2) 0.0621(10) Uani 1 1 d . . . . .
H00A H 0.6871 0.4993 0.7553 0.074 Uiso 1 1 calc R . . . .
C00B C 0.5905(3) 1.0129(6) 0.7423(2) 0.0630(10) Uani 1 1 d . . . . .
H00B H 0.5662 1.1427 0.7391 0.076 Uiso 1 1 calc R . . . .
C00C C 0.6268(2) 0.5683(6) 0.2412(2) 0.0586(10) Uani 1 1 d . . . . .
C00D C 0.5912(3) 0.8967(5) 0.6698(2) 0.0604(10) Uani 1 1 d . . . . .
H00D H 0.5676 0.9483 0.6174 0.072 Uiso 1 1 calc R . . . .
C00E C 0.6632(3) 0.7449(6) 0.8248(2) 0.0641(10) Uani 1 1 d . . . . .
H00E H 0.6883 0.6948 0.8771 0.077 Uiso 1 1 calc R . . . .
C00F C 0.6258(3) 0.9367(6) 0.8196(2) 0.0629(10) Uani 1 1 d . . . . .
C00G C 0.5842(3) 0.4055(6) 0.1973(2) 0.0735(12) Uani 1 1 d . . . . .
H00G H 0.5590 0.3024 0.2284 0.088 Uiso 1 1 calc R . . . .
C00H C 0.6612(3) 0.7185(7) 0.1912(3) 0.0806(13) Uani 1 1 d . . . . .
H00H H 0.6891 0.8310 0.2174 0.097 Uiso 1 1 calc R . . . .
C00I C 0.6535(3) 0.7811(6) 0.3786(2) 0.0793(13) Uani 1 1 d . . . . .
H00C H 0.7176 0.8126 0.3695 0.095 Uiso 1 1 calc R . . . .
H00F H 0.6155 0.8819 0.3478 0.095 Uiso 1 1 calc R . . . .
C00J C 0.6132(3) 0.5458(8) 0.0623(3) 0.0815(14) Uani 1 1 d . . . . .
H00J H 0.6080 0.5393 0.0028 0.098 Uiso 1 1 calc R . . . .
C00K C 0.5785(3) 0.3933(7) 0.1098(3) 0.0871(14) Uani 1 1 d . . . . .
H00K H 0.5511 0.2815 0.0824 0.105 Uiso 1 1 calc R . . . .
C00L C 0.6422(4) 0.8096(6) 0.4698(2) 0.0874(14) Uani 1 1 d . . . . .
H00I H 0.5890 0.8960 0.4759 0.105 Uiso 1 1 calc R . . . .
H00L H 0.6966 0.8786 0.4957 0.105 Uiso 1 1 calc R . . . .
C00M C 0.6548(3) 0.7043(8) 0.1025(3) 0.0894(14) Uani 1 1 d . . . . .
H00M H 0.6796 0.8060 0.0704 0.107 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
Cl1 C00F 1.729(4) . ?
N002 N003 1.373(4) . ?
N002 C005 1.341(4) . ?
N002 C007 1.420(4) . ?
N003 N004 1.301(4) . ?
N004 C008 1.361(4) . ?
C005 C008 1.368(4) . ?
C005 C00L 1.476(5) . ?
C006 C009 1.338(5) . ?
C006 C00C 1.476(5) . ?
C006 C00I 1.514(5) . ?
C007 C00A 1.378(5) . ?
C007 C00D 1.380(5) . ?
C008 C009 1.431(5) . ?
C009 H009 0.9300 . ?
C00A H00A 0.9300 . ?
C00A C00E 1.374(5) . ?
C00B H00B 0.9300 . ?
C00B C00D 1.373(5) . ?
C00B C00F 1.372(5) . ?
C00C C00G 1.398(5) . ?
C00C C00H 1.383(5) . ?
C00D H00D 0.9300 . ?
C00E H00E 0.9300 . ?
C00E C00F 1.383(5) . ?
C00G H00G 0.9300 . ?
C00G C00K 1.368(5) . ?
C00H H00H 0.9300 . ?
C00H C00M 1.387(6) . ?
C00I H00C 0.9700 . ?
C00I H00F 0.9700 . ?
C00I C00L 1.462(5) . ?
C00J H00J 0.9300 . ?
C00J C00K 1.373(6) . ?
C00J C00M 1.343(6) . ?
C00K H00K 0.9300 . ?
C00L H00I 0.9700 . ?
C00L H00L 0.9700 . ?
C00M H00M 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
N003 N002 C007 117.7(3) . . ?
C005 N002 N003 109.9(3) . . ?
C005 N002 C007 132.4(3) . . ?
N004 N003 N002 107.1(3) . . ?
N003 N004 C008 109.2(3) . . ?
N002 C005 C008 105.4(3) . . ?
N002 C005 C00L 132.9(3) . . ?
C008 C005 C00L 121.7(3) . . ?
C009 C006 C00C 122.4(3) . . ?
C009 C006 C00I 118.6(3) . . ?
C00C C006 C00I 119.1(3) . . ?
C00A C007 N002 119.7(3) . . ?
C00A C007 C00D 119.5(3) . . ?
C00D C007 N002 120.7(3) . . ?
N004 C008 C005 108.4(3) . . ?
N004 C008 C009 128.9(3) . . ?
C005 C008 C009 122.7(3) . . ?
C006 C009 C008 120.9(3) . . ?
C006 C009 H009 119.6 . . ?
C008 C009 H009 119.6 . . ?
C007 C00A H00A 119.7 . . ?
C00E C00A C007 120.5(4) . . ?
C00E C00A H00A 119.7 . . ?
C00D C00B H00B 120.2 . . ?
C00D C00B C00F 119.7(4) . . ?
C00F C00B H00B 120.2 . . ?
C00G C00C C006 121.3(3) . . ?
C00H C00C C006 122.4(4) . . ?
C00H C00C C00G 116.3(4) . . ?
C007 C00D H00D 119.8 . . ?
C00B C00D C007 120.4(3) . . ?
C00B C00D H00D 119.8 . . ?
C00A C00E H00E 120.4 . . ?
C00A C00E C00F 119.3(3) . . ?
C00F C00E H00E 120.4 . . ?
C00B C00F Cl1 119.5(3) . . ?
C00B C00F C00E 120.6(3) . . ?
C00E C00F Cl1 119.9(3) . . ?
C00C C00G H00G 119.1 . . ?
C00K C00G C00C 121.9(4) . . ?
C00K C00G H00G 119.1 . . ?
C00C C00H H00H 119.4 . . ?
C00C C00H C00M 121.2(4) . . ?
C00M C00H H00H 119.4 . . ?
C006 C00I H00C 107.1 . . ?
C006 C00I H00F 107.1 . . ?
H00C C00I H00F 106.8 . . ?
C00L C00I C006 120.9(3) . . ?
C00L C00I H00C 107.1 . . ?
C00L C00I H00F 107.1 . . ?
C00K C00J H00J 120.3 . . ?
C00M C00J H00J 120.3 . . ?
C00M C00J C00K 119.5(4) . . ?
C00G C00K C00J 120.2(4) . . ?
C00G C00K H00K 119.9 . . ?
C00J C00K H00K 119.9 . . ?
C005 C00L H00I 108.7 . . ?
C005 C00L H00L 108.7 . . ?
C00I C00L C005 114.1(3) . . ?
C00I C00L H00I 108.7 . . ?
C00I C00L H00L 108.7 . . ?
H00I C00L H00L 107.6 . . ?
C00H C00M H00M 119.5 . . ?
C00J C00M C00H 121.0(4) . . ?
C00J C00M H00M 119.5 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.990
_oxdiff_exptl_absorpt_empirical_full_min 0.385
####################################################################### 
# 
# 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_dbr110_0m
_database_code_depnum_ccdc_archive 'CCDC 1936273'
loop_
_audit_author_name
_audit_author_address
'Dr. Raghavaiah Pallepogu'
;Assistant Professor
India
;
_audit_update_record             
;
2019-06-25 deposited with the CCDC.	2019-08-19 downloaded from the CCDC.
;
_audit_creation_date             2019-05-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         '2(C23 H16 N4)'
_chemical_formula_sum            'C46 H32 N8'
_chemical_formula_weight         696.79
_chemical_absolute_configuration ?
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_H-M_alt        'C 1 c 1'
_space_group_name_Hall           'C -2yc'
loop_
_space_group_symop_operation_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'

_cell_length_a                   13.055(5)
_cell_length_b                   13.601(5)
_cell_length_c                   10.697(5)
_cell_angle_alpha                90.000(5)
_cell_angle_beta                 100.788(5)
_cell_angle_gamma                90.000(5)
_cell_volume                     1865.8(13)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9944
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.928
_cell_measurement_theta_min      3.398
_shelx_estimated_absorpt_T_max   0.991
_shelx_estimated_absorpt_T_min   0.985
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.7078
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.240
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             728
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0347
_diffrn_reflns_av_unetI/netI     0.0178
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            40187
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.571
_diffrn_reflns_theta_min         2.715
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.993
_reflns_Friedel_fraction_full    0.990
_reflns_Friedel_fraction_max     0.989
_reflns_number_gt                3656
_reflns_number_total             4255
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    ?
_refine_diff_density_max         0.541
_refine_diff_density_min         -0.217
_refine_diff_density_rms         0.036
_refine_ls_abs_structure_details 
;
 Flack x determined using 1557 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.5(4)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         4255
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0770
_refine_ls_R_factor_gt           0.0668
_refine_ls_restrained_S_all      1.071
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0740P)²+1.4562P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1683
_refine_ls_wR_factor_ref         0.1755
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C1(H1), C22(H22), C4(H4), C10(H10), C18(H18), C12(H12), C9(H9),
 C2(H2), C13(H13), C16(H16), C20(H20), C21(H21), C14(H14), C19(H19), C15(H15)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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
N1 N 0.7864(3) 0.3091(2) 0.3095(3) 0.0534(8) Uani 1 1 d . . . . .
N2 N 0.8276(3) 0.3953(3) 0.3590(4) 0.0667(10) Uani 1 1 d . . . . .
C17 C 0.6686(3) 0.1758(3) 0.3638(4) 0.0538(9) Uani 1 1 d . . . . .
N3 N 0.7978(4) 0.4065(3) 0.4683(4) 0.0768(12) Uani 1 1 d . . . . .
C5 C 0.8270(3) 0.1757(3) 0.1769(4) 0.0565(10) Uani 1 1 d . . . . .
H5 H 0.823133 0.131947 0.242687 0.068 Uiso 1 1 calc R . . . .
C1 C 0.8205(3) 0.3412(4) 0.0983(4) 0.0617(11) Uani 1 1 d . . . . .
H1 H 0.810846 0.407981 0.110884 0.074 Uiso 1 1 calc R . . . .
C22 C 0.5894(4) 0.1681(5) 0.2585(5) 0.0755(14) Uani 1 1 d . . . . .
H22 H 0.576583 0.220336 0.201625 0.091 Uiso 1 1 calc R . . . .
C6 C 0.8114(3) 0.2740(3) 0.1931(4) 0.0491(8) Uani 1 1 d . . . . .
C7 C 0.7297(3) 0.2657(3) 0.3895(4) 0.0527(9) Uani 1 1 d . . . . .
C4 C 0.8485(3) 0.1413(4) 0.0633(4) 0.0620(10) Uani 1 1 d . . . . .
H4 H 0.857374 0.074362 0.051228 0.074 Uiso 1 1 calc R . . . .
C8 C 0.7373(4) 0.3287(4) 0.4900(4) 0.0667(11) Uani 1 1 d . . . . .
C10 C 0.6719(5) 0.3827(5) 0.6803(5) 0.0776(14) Uani 1 1 d . . . . .
H10 H 0.704102 0.442848 0.673215 0.093 Uiso 1 1 calc R . . . .
C18 C 0.6853(4) 0.0968(4) 0.4461(5) 0.0741(13) Uani 1 1 d . . . . .
H18 H 0.738180 0.099477 0.517649 0.089 Uiso 1 1 calc R . . . .
C12 C 0.5870(5) 0.2791(4) 0.8305(5) 0.0732(12) Uani 1 1 d . . . . .
H12 H 0.604197 0.221340 0.792775 0.088 Uiso 1 1 calc R . . . .
C9 C 0.6810(5) 0.3169(4) 0.6000(5) 0.0790(14) Uani 1 1 d . . . . .
H9 H 0.650457 0.256232 0.609307 0.095 Uiso 1 1 calc R . . . .
C3 C 0.8567(4) 0.2080(5) -0.0330(4) 0.0708(13) Uani 1 1 d . . . . .
C2 C 0.8441(4) 0.3081(4) -0.0147(5) 0.0724(13) Uani 1 1 d . . . . .
H2 H 0.851537 0.352590 -0.078448 0.087 Uiso 1 1 calc R . . . .
C13 C 0.5353(4) 0.2751(4) 0.9314(5) 0.0748(13) Uani 1 1 d . . . . .
H13 H 0.517045 0.214799 0.961863 0.090 Uiso 1 1 calc R . . . .
N4 N 0.8840(6) 0.1405(6) -0.2499(5) 0.131(3) Uani 1 1 d . . . . .
C16 C 0.5882(5) 0.4537(4) 0.8413(6) 0.0820(14) Uani 1 1 d . . . . .
H16 H 0.605535 0.514535 0.811587 0.098 Uiso 1 1 calc R . . . .
C20 C 0.5463(5) 0.0080(5) 0.3169(7) 0.0987(19) Uani 1 1 d . . . . .
H20 H 0.505975 -0.048553 0.301198 0.118 Uiso 1 1 calc R . . . .
C23 C 0.8724(5) 0.1734(6) -0.1549(6) 0.094(2) Uani 1 1 d . . . . .
C21 C 0.5289(4) 0.0844(5) 0.2361(7) 0.0928(18) Uani 1 1 d . . . . .
H21 H 0.475969 0.080914 0.164751 0.111 Uiso 1 1 calc R . . . .
C11 C 0.6136(4) 0.3704(5) 0.7847(5) 0.0727(14) Uani 1 1 d . . . . .
C14 C 0.5111(4) 0.3604(5) 0.9863(5) 0.0821(17) Uani 1 1 d . . . . .
H14 H 0.476539 0.358393 1.054844 0.099 Uiso 1 1 calc R . . . .
C19 C 0.6239(6) 0.0138(5) 0.4226(7) 0.099(2) Uani 1 1 d . . . . .
H19 H 0.635208 -0.038788 0.479126 0.118 Uiso 1 1 calc R . . . .
C15 C 0.5376(5) 0.4490(5) 0.9406(6) 0.0921(18) Uani 1 1 d . . . . .
H15 H 0.520650 0.506842 0.978432 0.111 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 N2 1.356(5) . ?
N1 C6 1.427(5) . ?
N1 C7 1.367(5) . ?
N2 N3 1.309(6) . ?
C17 C22 1.384(6) . ?
C17 C7 1.458(6) . ?
C17 C18 1.381(6) . ?
N3 C8 1.366(7) . ?
C5 C6 1.369(6) . ?
C5 C4 1.379(6) . ?
C1 C6 1.387(6) . ?
C1 C2 1.377(7) . ?
C22 C21 1.380(8) . ?
C7 C8 1.363(6) . ?
C4 C3 1.392(7) . ?
C8 C9 1.508(7) . ?
C10 C9 1.261(7) . ?
C10 C11 1.474(7) . ?
C18 C19 1.380(8) . ?
C12 C13 1.377(7) . ?
C12 C11 1.402(8) . ?
C3 C2 1.390(8) . ?
C3 C23 1.436(8) . ?
C13 C14 1.364(8) . ?
N4 C23 1.146(8) . ?
C16 C11 1.354(8) . ?
C16 C15 1.353(9) . ?
C20 C21 1.344(9) . ?
C20 C19 1.372(9) . ?
C14 C15 1.369(9) . ?

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 C6 119.4(3) . . ?
N2 N1 C7 110.5(3) . . ?
C7 N1 C6 129.9(3) . . ?
N3 N2 N1 106.6(4) . . ?
C22 C17 C7 121.1(4) . . ?
C18 C17 C22 117.7(4) . . ?
C18 C17 C7 121.1(4) . . ?
N2 N3 C8 109.9(4) . . ?
C6 C5 C4 120.2(4) . . ?
C2 C1 C6 119.4(4) . . ?
C21 C22 C17 121.3(5) . . ?
C5 C6 N1 120.1(3) . . ?
C5 C6 C1 121.1(4) . . ?
C1 C6 N1 118.9(4) . . ?
N1 C7 C17 125.8(4) . . ?
C8 C7 N1 104.7(4) . . ?
C8 C7 C17 129.2(4) . . ?
C5 C4 C3 119.2(4) . . ?
N3 C8 C9 126.6(5) . . ?
C7 C8 N3 108.2(4) . . ?
C7 C8 C9 125.0(5) . . ?
C9 C10 C11 124.4(6) . . ?
C19 C18 C17 120.2(5) . . ?
C13 C12 C11 119.9(5) . . ?
C10 C9 C8 125.3(6) . . ?
C4 C3 C23 120.1(6) . . ?
C2 C3 C4 120.4(4) . . ?
C2 C3 C23 119.3(5) . . ?
C1 C2 C3 119.7(4) . . ?
C14 C13 C12 119.4(5) . . ?
C15 C16 C11 120.5(6) . . ?
C21 C20 C19 119.7(6) . . ?
N4 C23 C3 176.1(9) . . ?
C20 C21 C22 120.2(5) . . ?
C12 C11 C10 124.2(5) . . ?
C16 C11 C10 116.7(5) . . ?
C16 C11 C12 119.1(5) . . ?
C13 C14 C15 120.0(5) . . ?
C20 C19 C18 120.7(5) . . ?
C16 C15 C14 121.0(6) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_dbr109_0m
_database_code_depnum_ccdc_archive 'CCDC 1936274'
loop_
_audit_author_name
_audit_author_address
'Dr. Raghavaiah Pallepogu'
;Assistant Professor
India
;
_audit_update_record             
;
2019-06-25 deposited with the CCDC.	2019-08-19 downloaded from the CCDC.
;
_audit_creation_date             2019-05-21
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         '2(C23 H14 F N3 O2)'
_chemical_formula_sum            'C46 H28 F2 N6 O4'
_chemical_formula_weight         766.74
_chemical_melting_point          ?
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'
F F 0.0171 0.0103 '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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.293(5)
_cell_length_b                   13.946(5)
_cell_length_c                   16.068(5)
_cell_angle_alpha                114.567(5)
_cell_angle_beta                 99.860(5)
_cell_angle_gamma                93.392(5)
_cell_volume                     1846.1(13)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9250
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      2.39
_cell_measurement_theta_min      26.04
_shelx_estimated_absorpt_T_max   0.987
_shelx_estimated_absorpt_T_min   0.981
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.7005
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.1243 before and 0.0561 after correction.
The Ratio of minimum to maximum transmission is 0.9398.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.379
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.14
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0613
_diffrn_reflns_av_unetI/netI     0.0277
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            75290
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.449
_diffrn_reflns_theta_min         2.248
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5448
_reflns_number_total             7592
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.174
_refine_diff_density_min         -0.200
_refine_diff_density_rms         0.037
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     523
_refine_ls_number_reflns         7592
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0733
_refine_ls_R_factor_gt           0.0461
_refine_ls_restrained_S_all      1.057
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0425P)²+0.6139P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1047
_refine_ls_wR_factor_ref         0.1164
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C13(H13), C36(H36), C40(H40), C23(H23), C22(H22), C17(H17), C27(H27),
 C42(H42), C7(H7), C19(H19), C37(H37), C24(H24), C30(H30), C46(H46), C39(H39),
 C38(H38), C43(H43), C20(H20), C26(H26), C25(H25), C14(H14), C15(H15), C45(H45),
  C16(H16), C1(H1), C4(H4), C2(H2), C3(H3)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?
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
O3 O 0.23883(14) 0.56092(9) 0.76821(9) 0.0510(3) Uani 1 1 d . . . . .
O2 O 0.46486(16) 0.78864(11) 0.67176(10) 0.0636(4) Uani 1 1 d . . . . .
F1 F 0.05089(16) 0.99891(13) 0.20686(9) 0.0910(5) Uani 1 1 d . . . . .
O4 O 0.16250(16) 0.58260(10) 0.89600(10) 0.0606(4) Uani 1 1 d . . . . .
O1 O 0.41222(16) 0.81186(10) 0.80679(9) 0.0573(3) Uani 1 1 d . . . . .
N6 N 0.20549(15) 0.33658(10) 0.99940(9) 0.0413(3) Uani 1 1 d . . . . .
N4 N 0.20644(17) 0.26953(11) 0.85338(10) 0.0467(4) Uani 1 1 d . . . . .
N3 N 0.28853(15) 0.99147(10) 0.54187(9) 0.0411(3) Uani 1 1 d . . . . .
N1 N 0.38693(18) 1.07475(11) 0.68865(10) 0.0501(4) Uani 1 1 d . . . . .
F2 F 0.1652(2) 0.28780(15) 1.31731(10) 0.1095(6) Uani 1 1 d . . . . .
N5 N 0.19040(18) 0.24472(11) 0.92075(11) 0.0509(4) Uani 1 1 d . . . . .
C34 C 0.23174(17) 0.42266(12) 0.98123(11) 0.0361(4) Uani 1 1 d . . . . .
C12 C 0.20922(18) 0.80536(13) 0.51899(11) 0.0391(4) Uani 1 1 d . . . . .
N2 N 0.35637(18) 1.08717(11) 0.61169(10) 0.0519(4) Uani 1 1 d . . . . .
C35 C 0.25272(17) 0.53279(12) 1.05503(11) 0.0367(4) Uani 1 1 d . . . . .
C11 C 0.27578(18) 0.91718(12) 0.57548(11) 0.0371(4) Uani 1 1 d . . . . .
C13 C 0.2559(2) 0.74238(14) 0.43879(13) 0.0518(5) Uani 1 1 d . . . . .
H13 H 0.328252 0.771437 0.419009 0.062 Uiso 1 1 calc R . . . .
C18 C 0.22837(18) 0.98774(13) 0.45204(11) 0.0390(4) Uani 1 1 d . . . . .
C41 C 0.19519(19) 0.32857(13) 1.08433(12) 0.0421(4) Uani 1 1 d . . . . .
C36 C 0.37680(18) 0.60368(13) 1.07030(13) 0.0448(4) Uani 1 1 d . . . . .
H36 H 0.445946 0.581797 1.033181 0.054 Uiso 1 1 calc R . . . .
C31 C 0.25501(17) 0.42075(13) 0.81995(11) 0.0386(4) Uani 1 1 d . . . . .
C40 C 0.14942(19) 0.56697(14) 1.10934(12) 0.0452(4) Uani 1 1 d . . . . .
H40 H 0.065839 0.520362 1.099672 0.054 Uiso 1 1 calc R . . . .
C23 C 0.08831(19) 0.93481(13) 0.40355(12) 0.0428(4) Uani 1 1 d . . . . .
H23 H 0.034216 0.897731 0.427305 0.051 Uiso 1 1 calc R . . . .
C22 C 0.0290(2) 0.93712(15) 0.31979(13) 0.0508(5) Uani 1 1 d . . . . .
H22 H -0.064256 0.900518 0.285532 0.061 Uiso 1 1 calc R . . . .
C17 C 0.1010(2) 0.76081(15) 0.54698(14) 0.0533(5) Uani 1 1 d . . . . .
H17 H 0.068829 0.802383 0.600782 0.064 Uiso 1 1 calc R . . . .
C27 C 0.3005(2) 0.54109(16) 0.62585(14) 0.0551(5) Uani 1 1 d . . . . .
H27 H 0.277413 0.608760 0.637058 0.066 Uiso 1 1 calc R . . . .
C42 C 0.0719(2) 0.27042(16) 1.08477(14) 0.0550(5) Uani 1 1 d . . . . .
H42 H -0.005050 0.240727 1.032105 0.066 Uiso 1 1 calc R . . . .
C33 C 0.23259(17) 0.37826(12) 0.88676(11) 0.0375(4) Uani 1 1 d . . . . .
C7 C 0.3052(2) 0.99760(14) 0.82495(12) 0.0465(4) Uani 1 1 d . . . . .
H7 H 0.271094 1.061353 0.832150 0.056 Uiso 1 1 calc R . . . .
C10 C 0.33878(18) 0.97231(13) 0.66968(11) 0.0403(4) Uani 1 1 d . . . . .
C29 C 0.32233(19) 0.39914(14) 0.67443(12) 0.0448(4) Uani 1 1 d . . . . .
C19 C 0.3092(2) 1.04347(15) 0.41761(13) 0.0493(4) Uani 1 1 d . . . . .
H19 H 0.404155 1.077906 0.450053 0.059 Uiso 1 1 calc R . . . .
C37 C 0.3978(2) 0.70603(14) 1.14003(14) 0.0520(5) Uani 1 1 d . . . . .
H37 H 0.481904 0.752680 1.150670 0.062 Uiso 1 1 calc R . . . .
C24 C 0.3704(2) 0.34016(17) 0.59264(14) 0.0593(5) Uani 1 1 d . . . . .
H24 H 0.394603 0.272725 0.581292 0.071 Uiso 1 1 calc R . . . .
C30 C 0.30476(19) 0.36215(14) 0.74269(12) 0.0443(4) Uani 1 1 d . . . . .
H30 H 0.328387 0.295187 0.733813 0.053 Uiso 1 1 calc R . . . .
C8 C 0.34943(19) 0.93928(13) 0.74584(12) 0.0407(4) Uani 1 1 d . . . . .
C28 C 0.28858(19) 0.49979(14) 0.68910(12) 0.0446(4) Uani 1 1 d . . . . .
C6 C 0.3091(2) 0.96465(14) 0.89839(12) 0.0476(4) Uani 1 1 d . . . . .
C46 C 0.3100(2) 0.37361(17) 1.16208(14) 0.0609(5) Uani 1 1 d . . . . .
H46 H 0.394076 0.412659 1.161331 0.073 Uiso 1 1 calc R . . . .
C32 C 0.21474(19) 0.52507(13) 0.83319(12) 0.0424(4) Uani 1 1 d . . . . .
C39 C 0.1703(2) 0.67050(15) 1.17808(13) 0.0547(5) Uani 1 1 d . . . . .
H39 H 0.099789 0.693769 1.213884 0.066 Uiso 1 1 calc R . . . .
C9 C 0.4123(2) 0.84295(14) 0.73619(13) 0.0460(4) Uani 1 1 d . . . . .
C38 C 0.2949(2) 0.73930(14) 1.19382(13) 0.0551(5) Uani 1 1 d . . . . .
H38 H 0.309408 0.808456 1.241007 0.066 Uiso 1 1 calc R . . . .
C21 C 0.1106(2) 0.99457(17) 0.28837(13) 0.0561(5) Uani 1 1 d . . . . .
C5 C 0.3612(2) 0.86990(15) 0.88600(13) 0.0494(4) Uani 1 1 d . . . . .
C43 C 0.0618(3) 0.25588(19) 1.16353(16) 0.0690(6) Uani 1 1 d . . . . .
H43 H -0.021054 0.216005 1.164672 0.083 Uiso 1 1 calc R . . . .
C20 C 0.2486(2) 1.04788(17) 0.33487(14) 0.0579(5) Uani 1 1 d . . . . .
H20 H 0.300836 1.086359 0.311433 0.070 Uiso 1 1 calc R . . . .
C26 C 0.3471(2) 0.48045(18) 0.54592(15) 0.0612(5) Uani 1 1 d . . . . .
H26 H 0.355058 0.507395 0.502526 0.073 Uiso 1 1 calc R . . . .
C25 C 0.3825(2) 0.37993(19) 0.52877(15) 0.0647(6) Uani 1 1 d . . . . .
H25 H 0.414243 0.339702 0.474412 0.078 Uiso 1 1 calc R . . . .
C14 C 0.1952(3) 0.63622(16) 0.38799(15) 0.0655(6) Uani 1 1 d . . . . .
H14 H 0.227164 0.593932 0.334355 0.079 Uiso 1 1 calc R . . . .
C15 C 0.0877(3) 0.59323(16) 0.41666(17) 0.0697(6) Uani 1 1 d . . . . .
H15 H 0.047088 0.521884 0.382284 0.084 Uiso 1 1 calc R . . . .
C45 C 0.2981(3) 0.3597(2) 1.24090(16) 0.0744(7) Uani 1 1 d . . . . .
H45 H 0.373458 0.390324 1.294415 0.089 Uiso 1 1 calc R . . . .
C16 C 0.0403(2) 0.65475(17) 0.49542(17) 0.0673(6) Uani 1 1 d . . . . .
H16 H -0.032849 0.625351 0.514394 0.081 Uiso 1 1 calc R . . . .
C44 C 0.1759(3) 0.30126(19) 1.23944(16) 0.0680(6) Uani 1 1 d . . . . .
C1 C 0.2585(3) 1.02037(18) 0.97961(14) 0.0663(6) Uani 1 1 d . . . . .
H1 H 0.223115 1.084302 0.989176 0.080 Uiso 1 1 calc R . . . .
C4 C 0.3630(3) 0.83030(18) 0.95184(16) 0.0699(6) Uani 1 1 d . . . . .
H4 H 0.397618 0.766199 0.942601 0.084 Uiso 1 1 calc R . . . .
C2 C 0.2603(3) 0.9821(2) 1.04542(16) 0.0763(7) Uani 1 1 d . . . . .
H2 H 0.226406 1.019828 1.099510 0.092 Uiso 1 1 calc R . . . .
C3 C 0.3126(3) 0.8874(2) 1.03126(17) 0.0761(7) Uani 1 1 d . . . . .
H3 H 0.313848 0.861712 1.076260 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
O3 C28 1.380(2) . ?
O3 C32 1.375(2) . ?
O2 C9 1.204(2) . ?
F1 C21 1.359(2) . ?
O4 C32 1.199(2) . ?
O1 C9 1.373(2) . ?
O1 C5 1.377(2) . ?
N6 N5 1.3527(19) . ?
N6 C34 1.366(2) . ?
N6 C41 1.433(2) . ?
N4 N5 1.294(2) . ?
N4 C33 1.372(2) . ?
N3 N2 1.3603(19) . ?
N3 C11 1.361(2) . ?
N3 C18 1.434(2) . ?
N1 N2 1.305(2) . ?
N1 C10 1.360(2) . ?
F2 C44 1.359(2) . ?
C34 C35 1.474(2) . ?
C34 C33 1.382(2) . ?
C12 C11 1.468(2) . ?
C12 C13 1.384(2) . ?
C12 C17 1.383(3) . ?
C35 C36 1.391(2) . ?
C35 C40 1.380(2) . ?
C11 C10 1.379(2) . ?
C13 C14 1.384(3) . ?
C18 C23 1.381(2) . ?
C18 C19 1.380(2) . ?
C41 C42 1.367(3) . ?
C41 C46 1.381(3) . ?
C36 C37 1.376(2) . ?
C31 C33 1.462(2) . ?
C31 C30 1.349(2) . ?
C31 C32 1.462(2) . ?
C40 C39 1.382(3) . ?
C23 C22 1.379(2) . ?
C22 C21 1.367(3) . ?
C17 C16 1.384(3) . ?
C27 C28 1.377(3) . ?
C27 C26 1.372(3) . ?
C42 C43 1.379(3) . ?
C7 C8 1.343(2) . ?
C7 C6 1.430(2) . ?
C10 C8 1.467(2) . ?
C29 C24 1.396(3) . ?
C29 C30 1.420(2) . ?
C29 C28 1.388(3) . ?
C19 C20 1.380(3) . ?
C37 C38 1.370(3) . ?
C24 C25 1.371(3) . ?
C8 C9 1.456(2) . ?
C6 C5 1.382(3) . ?
C6 C1 1.392(3) . ?
C46 C45 1.379(3) . ?
C39 C38 1.376(3) . ?
C21 C20 1.361(3) . ?
C5 C4 1.380(3) . ?
C43 C44 1.360(3) . ?
C26 C25 1.383(3) . ?
C14 C15 1.373(3) . ?
C15 C16 1.366(3) . ?
C45 C44 1.350(3) . ?
C1 C2 1.367(3) . ?
C4 C3 1.373(3) . ?
C2 C3 1.377(3) . ?

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
C32 O3 C28 122.80(14) . . ?
C9 O1 C5 122.71(14) . . ?
N5 N6 C34 110.71(14) . . ?
N5 N6 C41 117.52(14) . . ?
C34 N6 C41 131.75(14) . . ?
N5 N4 C33 109.71(14) . . ?
N2 N3 C11 110.74(13) . . ?
N2 N3 C18 117.69(13) . . ?
C11 N3 C18 131.06(13) . . ?
N2 N1 C10 109.24(14) . . ?
N4 N5 N6 107.61(13) . . ?
N6 C34 C35 121.87(15) . . ?
N6 C34 C33 103.98(14) . . ?
C33 C34 C35 134.14(15) . . ?
C13 C12 C11 120.88(16) . . ?
C17 C12 C11 120.01(16) . . ?
C17 C12 C13 119.09(16) . . ?
N1 N2 N3 107.22(13) . . ?
C36 C35 C34 120.21(15) . . ?
C40 C35 C34 120.57(15) . . ?
C40 C35 C36 119.23(15) . . ?
N3 C11 C12 125.07(15) . . ?
N3 C11 C10 103.84(14) . . ?
C10 C11 C12 131.09(15) . . ?
C14 C13 C12 120.09(19) . . ?
C23 C18 N3 120.54(15) . . ?
C19 C18 N3 118.79(15) . . ?
C19 C18 C23 120.55(16) . . ?
C42 C41 N6 118.21(16) . . ?
C42 C41 C46 120.81(18) . . ?
C46 C41 N6 120.89(17) . . ?
C37 C36 C35 120.35(17) . . ?
C30 C31 C33 120.76(15) . . ?
C30 C31 C32 119.04(16) . . ?
C32 C31 C33 120.09(15) . . ?
C35 C40 C39 119.94(17) . . ?
C22 C23 C18 119.76(17) . . ?
C21 C22 C23 118.32(18) . . ?
C12 C17 C16 120.39(19) . . ?
C26 C27 C28 118.69(19) . . ?
C41 C42 C43 119.84(19) . . ?
N4 C33 C34 107.98(14) . . ?
N4 C33 C31 117.19(14) . . ?
C34 C33 C31 134.83(15) . . ?
C8 C7 C6 121.99(17) . . ?
N1 C10 C11 108.95(15) . . ?
N1 C10 C8 120.22(14) . . ?
C11 C10 C8 130.66(15) . . ?
C24 C29 C30 124.10(17) . . ?
C28 C29 C24 117.61(17) . . ?
C28 C29 C30 118.29(16) . . ?
C20 C19 C18 119.74(18) . . ?
C38 C37 C36 120.07(18) . . ?
C25 C24 C29 121.1(2) . . ?
C31 C30 C29 122.31(16) . . ?
C7 C8 C10 121.11(16) . . ?
C7 C8 C9 119.60(16) . . ?
C9 C8 C10 119.27(15) . . ?
O3 C28 C29 119.99(16) . . ?
C27 C28 O3 117.97(17) . . ?
C27 C28 C29 122.03(17) . . ?
C5 C6 C7 117.74(17) . . ?
C5 C6 C1 118.43(18) . . ?
C1 C6 C7 123.78(18) . . ?
C45 C46 C41 118.9(2) . . ?
O3 C32 C31 117.42(15) . . ?
O4 C32 O3 116.84(16) . . ?
O4 C32 C31 125.74(17) . . ?
C38 C39 C40 120.32(18) . . ?
O2 C9 O1 117.32(16) . . ?
O2 C9 C8 125.49(17) . . ?
O1 C9 C8 117.18(16) . . ?
C37 C38 C39 120.07(17) . . ?
F1 C21 C22 118.38(18) . . ?
F1 C21 C20 118.44(18) . . ?
C20 C21 C22 123.19(18) . . ?
O1 C5 C6 120.58(16) . . ?
O1 C5 C4 118.06(18) . . ?
C4 C5 C6 121.36(19) . . ?
C44 C43 C42 118.4(2) . . ?
C21 C20 C19 118.42(18) . . ?
C27 C26 C25 121.14(19) . . ?
C24 C25 C26 119.4(2) . . ?
C15 C14 C13 120.1(2) . . ?
C16 C15 C14 120.31(19) . . ?
C44 C45 C46 119.2(2) . . ?
C15 C16 C17 120.0(2) . . ?
F2 C44 C43 118.3(2) . . ?
C45 C44 F2 118.9(2) . . ?
C45 C44 C43 122.8(2) . . ?
C2 C1 C6 120.7(2) . . ?
C3 C4 C5 118.7(2) . . ?
C1 C2 C3 119.7(2) . . ?
C4 C3 C2 121.1(2) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
