# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2025

####################################################################### 
# 
# 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_gv-nn-01-g
_database_code_depnum_ccdc_archive 'CCDC 2211929'
loop_
_audit_author_name
_audit_author_address
'Govindarajan R'
;Pondicherry university
India
;
_audit_update_record             
;
2025-12-28 deposited with the CCDC.	2026-02-19 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT910_gv-nn-01-g          
;
PROBLEM: Missing FCF Reflection(s) Below Theta(Min)[Deg]= 4.09 Note
RESPONSE: These low-angle reflections were physically 
 obscured by the  beamstop during data collection due to the
 experimental geometry. Their absence does not impact the 
 final structural model or the  reliability of the refinement.
;

_audit_creation_date             2025-12-16
_audit_creation_method           
;
Olex2 1.5
(compiled 2025.07.13 svn.rb7424aed for OlexSys, GUI svn.r7308)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '0.727(C33 H22 N6 O3)'
_chemical_formula_sum            'C24 H16 N4.36 O2.18'
_chemical_formula_weight         400.41
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C26 H22 N2 O1'
_chemical_oxdiff_usercomment     'YELLOW COLOUR BLOCK, 295K, 0.52 0.20 0.28'
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'

_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      orthorhombic
_space_group_IT_number           56
_space_group_name_H-M_alt        'P c c n'
_space_group_name_Hall           '-P 2ab 2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z'
'x+1/2, -y, -z+1/2'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z'
'-x-1/2, y, z-1/2'
'x, -y-1/2, z-1/2'

_cell_length_a                   27.0007(18)
_cell_length_b                   21.4303(10)
_cell_length_c                   9.5534(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     5527.9(5)
_cell_formula_units_Z            11
_cell_measurement_reflns_used    5761
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      29.1431
_cell_measurement_theta_min      3.7655
_shelx_estimated_absorpt_T_max   0.983
_shelx_estimated_absorpt_T_min   0.956
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91999
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             2288
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0421
_diffrn_reflns_av_unetI/netI     0.0323
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.900
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -36
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            29729
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.900
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         29.208
_diffrn_reflns_theta_min         4.092
_diffrn_ambient_temperature      295(2)
_diffrn_detector_area_resol_mean 15.9821
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.900
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -25.00   23.00   1.0000   72.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.4178  -99.0000  150.0000 48

#__ type_ start__ end____ width___ exp.time_
  2 omega  -79.00  -37.00   1.0000   72.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.4178 -178.0000   60.0000 42

#__ type_ start__ end____ width___ exp.time_
  3 omega  -88.00  -62.00   1.0000   72.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.4178 -178.0000  -30.0000 26

#__ type_ start__ end____ width___ exp.time_
  4 omega  -87.00  -42.00   1.0000   72.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.4178 -178.0000   90.0000 45

#__ type_ start__ end____ width___ exp.time_
  5 omega   -2.00   34.00   1.0000   72.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.4178   57.0000   30.0000 36

#__ type_ start__ end____ width___ exp.time_
  6 omega  -11.00   55.00   1.0000   72.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.4178    0.0000  -60.0000 66

#__ type_ start__ end____ width___ exp.time_
  7 omega   -2.00   25.00   1.0000   72.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.4178  -19.0000 -120.0000 27
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0027788000
_diffrn_orient_matrix_UB_12      -0.0326216000
_diffrn_orient_matrix_UB_13      0.0098255000
_diffrn_orient_matrix_UB_21      0.0246779000
_diffrn_orient_matrix_UB_22      0.0047351000
_diffrn_orient_matrix_UB_23      0.0230600000
_diffrn_orient_matrix_UB_31      -0.0085458000
_diffrn_orient_matrix_UB_32      0.0030007000
_diffrn_orient_matrix_UB_33      0.0699027000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4623
_reflns_number_total             6745
_reflns_odcompleteness_completeness 99.33
_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, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXS  (Sheldrick, 2008)'
_refine_diff_density_max         0.180
_refine_diff_density_min         -0.182
_refine_diff_density_rms         0.035
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     389
_refine_ls_number_reflns         6745
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0824
_refine_ls_R_factor_gt           0.0500
_refine_ls_restrained_S_all      1.017
_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)+(0.0459P)²+1.5901P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1076
_refine_ls_wR_factor_ref         0.1232
_refine_special_details          ?
_olex2_refinement_description    
;
1.a Ternary CH refined with riding coordinates:
 C2(H2), C7(H7)
1.b Aromatic/amide H refined with riding coordinates:
 C13(H13), C16(H16), C18(H18), C19(H19), C22(H22), C23(H23), C24(H24),
 C25(H25), C26(H26), C27(H27), C29(H29), C33(H33)
1.c Idealised Me refined as rotating group:
 C30(H30A,H30B,H30C), C32(H32A,H32B,H32C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_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
O1 O 0.11493(5) 0.57190(6) 0.79568(11) 0.0524(3) Uani 1 1 d . . . . .
O2 O -0.00796(7) 0.77450(9) 1.4375(2) 0.1153(7) Uani 1 1 d . . . . .
O3 O 0.17851(11) 0.24770(7) 1.18846(17) 0.1295(9) Uani 1 1 d . . . . .
N1 N 0.15121(5) 0.60177(6) 1.00040(12) 0.0376(3) Uani 1 1 d . . . . .
N2 N 0.13686(5) 0.53706(6) 1.19174(11) 0.0338(3) Uani 1 1 d . . . . .
N3 N 0.27624(6) 0.61800(8) 1.21703(16) 0.0460(3) Uani 1 1 d . . . . .
H3A H 0.3072(9) 0.6023(10) 1.244(2) 0.067(6) Uiso 1 1 d . . . . .
H3B H 0.2747(7) 0.6601(10) 1.205(2) 0.061(6) Uiso 1 1 d . . . . .
N4 N 0.19353(6) 0.73961(7) 1.20536(19) 0.0618(4) Uani 1 1 d . . . . .
N5 N 0.31377(7) 0.46255(8) 1.3274(2) 0.0782(6) Uani 1 1 d . . . . .
N6 N 0.02735(7) 0.44575(9) 0.86709(17) 0.0687(5) Uani 1 1 d . . . . .
C1 C 0.15752(5) 0.58694(7) 1.12913(15) 0.0330(3) Uani 1 1 d . . . . .
C2 C 0.15047(6) 0.60384(7) 1.37862(15) 0.0377(3) Uani 1 1 d . . . . .
H2 H 0.169924 0.607054 1.464925 0.045 Uiso 1 1 calc R U . . .
C3 C 0.11916(6) 0.56268(7) 0.92108(15) 0.0381(3) Uani 1 1 d . . . . .
C4 C 0.18511(6) 0.62035(7) 1.24839(15) 0.0359(3) Uani 1 1 d . . . . .
C5 C 0.14197(6) 0.53376(7) 1.34397(14) 0.0354(3) Uani 1 1 d . . . . .
C6 C 0.09075(6) 0.51420(7) 0.99567(15) 0.0361(3) Uani 1 1 d . . . . .
C7 C 0.18971(6) 0.49679(7) 1.38140(16) 0.0398(4) Uani 1 1 d . . . . .
H7 H 0.192437 0.496237 1.483683 0.048 Uiso 1 1 calc R U . . .
C8 C 0.23530(6) 0.53035(7) 1.32491(16) 0.0416(4) Uani 1 1 d . . . . .
C9 C 0.23559(6) 0.58828(7) 1.26752(15) 0.0372(3) Uani 1 1 d . . . . .
C10 C 0.05530(6) 0.47739(8) 0.92197(16) 0.0459(4) Uani 1 1 d . . . . .
C11 C 0.18788(6) 0.42957(7) 1.33256(16) 0.0426(4) Uani 1 1 d . . . . .
C12 C 0.09880(5) 0.50412(7) 1.13529(14) 0.0335(3) Uani 1 1 d . . . . .
C13 C 0.06462(6) 0.64266(8) 1.30474(17) 0.0433(4) Uani 1 1 d . . . . .
H13 H 0.062810 0.611543 1.237080 0.052 Uiso 1 1 calc R U . . .
C14 C 0.18950(6) 0.68764(8) 1.22343(18) 0.0423(4) Uani 1 1 d . . . . .
C15 C 0.09615(6) 0.49648(7) 1.37840(15) 0.0385(4) Uani 1 1 d . . . . .
C16 C 0.03499(7) 0.43243(8) 1.25828(17) 0.0477(4) Uani 1 1 d . . . . .
H16 H 0.020689 0.417292 1.176480 0.057 Uiso 1 1 calc R U . . .
C17 C 0.07453(6) 0.47366(7) 1.25408(15) 0.0373(3) Uani 1 1 d . . . . .
C18 C 0.07801(7) 0.47843(8) 1.50700(17) 0.0499(4) Uani 1 1 d . . . . .
H18 H 0.091975 0.493351 1.589453 0.060 Uiso 1 1 calc R U . . .
C19 C 0.03847(8) 0.43752(9) 1.50989(19) 0.0602(5) Uani 1 1 d . . . . .
H19 H 0.025610 0.425110 1.595796 0.072 Uiso 1 1 calc R U . . .
C20 C 0.10594(6) 0.64568(7) 1.38990(16) 0.0408(4) Uani 1 1 d . . . . .
C21 C 0.27978(7) 0.49431(8) 1.3273(2) 0.0520(4) Uani 1 1 d . . . . .
C22 C 0.02590(7) 0.68452(8) 1.31715(19) 0.0519(4) Uani 1 1 d . . . . .
H22 H -0.001501 0.681354 1.258616 0.062 Uiso 1 1 calc R U . . .
C23 C 0.01757(8) 0.41460(9) 1.38838(19) 0.0600(5) Uani 1 1 d . . . . .
H23 H -0.008707 0.386661 1.394160 0.072 Uiso 1 1 calc R U . . .
C24 C 0.17741(8) 0.38216(8) 1.42473(19) 0.0592(5) Uani 1 1 d . . . . .
H24 H 0.172326 0.391711 1.518595 0.071 Uiso 1 1 calc R U . . .
C25 C 0.19614(8) 0.41386(8) 1.19349(18) 0.0540(5) Uani 1 1 d . . . . .
H25 H 0.203988 0.444970 1.129356 0.065 Uiso 1 1 calc R U . . .
C26 C 0.17422(10) 0.32058(9) 1.3818(2) 0.0756(7) Uani 1 1 d . . . . .
H26 H 0.167208 0.289176 1.446048 0.091 Uiso 1 1 calc R U . . .
C27 C 0.10680(8) 0.69244(11) 1.4897(2) 0.0772(7) Uani 1 1 d . . . . .
H27 H 0.133718 0.695428 1.550033 0.093 Uiso 1 1 calc R U . . .
C28 C 0.02812(8) 0.73062(10) 1.4160(3) 0.0707(6) Uani 1 1 d . . . . .
C29 C 0.19290(10) 0.35327(10) 1.1496(2) 0.0746(7) Uani 1 1 d . . . . .
H29 H 0.198389 0.343553 1.055954 0.090 Uiso 1 1 calc R U . . .
C30 C 0.1744(2) 0.19709(11) 1.2831(3) 0.164(2) Uani 1 1 d . . . . .
H30A H 0.175700 0.158506 1.232133 0.246 Uiso 1 1 calc R U . . .
H30B H 0.143495 0.199867 1.332307 0.246 Uiso 1 1 calc R U . . .
H30C H 0.201250 0.198587 1.348878 0.246 Uiso 1 1 calc R U . . .
C31 C 0.18155(11) 0.30655(9) 1.2433(2) 0.0794(7) Uani 1 1 d . . . . .
C32 C -0.05234(11) 0.76870(15) 1.3629(4) 0.1256(12) Uani 1 1 d . . . . .
H32A H -0.045808 0.772551 1.264547 0.188 Uiso 1 1 calc R U . . .
H32B H -0.074856 0.800932 1.391567 0.188 Uiso 1 1 calc R U . . .
H32C H -0.066801 0.728624 1.381584 0.188 Uiso 1 1 calc R U . . .
C33 C 0.06885(10) 0.73438(13) 1.5013(3) 0.0993(9) Uani 1 1 d . . . . .
H33 H 0.070690 0.765896 1.567974 0.119 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C3 1.2195(17) . ?
O2 C28 1.370(3) . ?
O2 C32 1.400(4) . ?
O3 C30 1.416(3) . ?
O3 C31 1.368(2) . ?
N1 C1 1.2816(18) . ?
N1 C3 1.423(2) . ?
N2 C1 1.3459(18) . ?
N2 C5 1.4626(17) . ?
N2 C12 1.3583(18) . ?
N3 H3A 0.94(2) . ?
N3 H3B 0.91(2) . ?
N3 C9 1.357(2) . ?
N4 C14 1.132(2) . ?
N5 C21 1.143(2) . ?
N6 C10 1.142(2) . ?
C1 C4 1.538(2) . ?
C2 H2 0.9800 . ?
C2 C4 1.596(2) . ?
C2 C5 1.555(2) . ?
C2 C20 1.504(2) . ?
C3 C6 1.475(2) . ?
C4 C9 1.537(2) . ?
C4 C14 1.466(2) . ?
C5 C7 1.555(2) . ?
C5 C15 1.509(2) . ?
C6 C10 1.426(2) . ?
C6 C12 1.369(2) . ?
C7 H7 0.9800 . ?
C7 C8 1.525(2) . ?
C7 C11 1.515(2) . ?
C8 C9 1.357(2) . ?
C8 C21 1.428(2) . ?
C11 C24 1.374(2) . ?
C11 C25 1.389(2) . ?
C12 C17 1.464(2) . ?
C13 H13 0.9300 . ?
C13 C20 1.382(2) . ?
C13 C22 1.383(2) . ?
C15 C17 1.411(2) . ?
C15 C18 1.378(2) . ?
C16 H16 0.9300 . ?
C16 C17 1.387(2) . ?
C16 C23 1.383(2) . ?
C18 H18 0.9300 . ?
C18 C19 1.382(2) . ?
C19 H19 0.9300 . ?
C19 C23 1.381(3) . ?
C20 C27 1.383(2) . ?
C22 H22 0.9300 . ?
C22 C28 1.368(3) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?
C24 C26 1.385(3) . ?
C25 H25 0.9300 . ?
C25 C29 1.367(3) . ?
C26 H26 0.9300 . ?
C26 C31 1.371(3) . ?
C27 H27 0.9300 . ?
C27 C33 1.367(3) . ?
C28 C33 1.371(3) . ?
C29 H29 0.9300 . ?
C29 C31 1.378(3) . ?
C30 H30A 0.9600 . ?
C30 H30B 0.9600 . ?
C30 H30C 0.9600 . ?
C32 H32A 0.9600 . ?
C32 H32B 0.9600 . ?
C32 H32C 0.9600 . ?
C33 H33 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
C28 O2 C32 118.1(2) . . ?
C31 O3 C30 117.78(18) . . ?
C1 N1 C3 116.48(12) . . ?
C1 N2 C5 116.18(11) . . ?
C1 N2 C12 123.36(12) . . ?
C12 N2 C5 116.17(11) . . ?
H3A N3 H3B 115.5(18) . . ?
C9 N3 H3A 116.9(13) . . ?
C9 N3 H3B 118.2(13) . . ?
N1 C1 N2 124.63(13) . . ?
N1 C1 C4 131.28(13) . . ?
N2 C1 C4 103.96(11) . . ?
C4 C2 H2 109.0 . . ?
C5 C2 H2 109.0 . . ?
C5 C2 C4 97.74(11) . . ?
C20 C2 H2 109.0 . . ?
C20 C2 C4 113.09(12) . . ?
C20 C2 C5 118.23(13) . . ?
O1 C3 N1 119.00(14) . . ?
O1 C3 C6 122.68(14) . . ?
N1 C3 C6 118.27(12) . . ?
C1 C4 C2 100.97(11) . . ?
C9 C4 C1 108.03(12) . . ?
C9 C4 C2 109.13(12) . . ?
C14 C4 C1 112.11(12) . . ?
C14 C4 C2 113.08(13) . . ?
C14 C4 C9 112.80(12) . . ?
N2 C5 C2 100.31(11) . . ?
N2 C5 C7 109.37(12) . . ?
N2 C5 C15 99.50(11) . . ?
C7 C5 C2 108.71(12) . . ?
C15 C5 C2 125.88(13) . . ?
C15 C5 C7 111.08(12) . . ?
C10 C6 C3 120.01(13) . . ?
C12 C6 C3 119.96(13) . . ?
C12 C6 C10 120.03(14) . . ?
C5 C7 H7 107.3 . . ?
C8 C7 C5 110.35(12) . . ?
C8 C7 H7 107.3 . . ?
C11 C7 C5 112.76(12) . . ?
C11 C7 H7 107.3 . . ?
C11 C7 C8 111.45(14) . . ?
C9 C8 C7 125.40(14) . . ?
C9 C8 C21 119.75(15) . . ?
C21 C8 C7 114.73(14) . . ?
N3 C9 C4 117.68(13) . . ?
C8 C9 N3 125.28(15) . . ?
C8 C9 C4 116.86(13) . . ?
N6 C10 C6 176.88(19) . . ?
C24 C11 C7 120.83(15) . . ?
C24 C11 C25 117.84(16) . . ?
C25 C11 C7 121.33(14) . . ?
N2 C12 C6 115.16(13) . . ?
N2 C12 C17 105.22(12) . . ?
C6 C12 C17 139.00(14) . . ?
C20 C13 H13 119.0 . . ?
C20 C13 C22 121.97(16) . . ?
C22 C13 H13 119.0 . . ?
N4 C14 C4 178.94(18) . . ?
C17 C15 C5 109.82(12) . . ?
C18 C15 C5 129.38(14) . . ?
C18 C15 C17 120.41(14) . . ?
C17 C16 H16 121.2 . . ?
C23 C16 H16 121.2 . . ?
C23 C16 C17 117.64(15) . . ?
C15 C17 C12 108.23(12) . . ?
C16 C17 C12 130.63(14) . . ?
C16 C17 C15 121.01(14) . . ?
C15 C18 H18 121.0 . . ?
C15 C18 C19 118.07(15) . . ?
C19 C18 H18 121.0 . . ?
C18 C19 H19 119.2 . . ?
C23 C19 C18 121.64(16) . . ?
C23 C19 H19 119.2 . . ?
C13 C20 C2 125.12(14) . . ?
C13 C20 C27 116.93(17) . . ?
C27 C20 C2 117.91(15) . . ?
N5 C21 C8 176.08(18) . . ?
C13 C22 H22 120.2 . . ?
C28 C22 C13 119.65(18) . . ?
C28 C22 H22 120.2 . . ?
C16 C23 H23 119.4 . . ?
C19 C23 C16 121.22(16) . . ?
C19 C23 H23 119.4 . . ?
C11 C24 H24 119.1 . . ?
C11 C24 C26 121.87(17) . . ?
C26 C24 H24 119.1 . . ?
C11 C25 H25 119.5 . . ?
C29 C25 C11 120.91(17) . . ?
C29 C25 H25 119.5 . . ?
C24 C26 H26 120.5 . . ?
C31 C26 C24 119.04(18) . . ?
C31 C26 H26 120.5 . . ?
C20 C27 H27 119.4 . . ?
C33 C27 C20 121.3(2) . . ?
C33 C27 H27 119.4 . . ?
O2 C28 C33 116.2(2) . . ?
C22 C28 O2 124.6(2) . . ?
C22 C28 C33 119.20(19) . . ?
C25 C29 H29 119.9 . . ?
C25 C29 C31 120.30(18) . . ?
C31 C29 H29 119.9 . . ?
O3 C30 H30A 109.5 . . ?
O3 C30 H30B 109.5 . . ?
O3 C30 H30C 109.5 . . ?
H30A C30 H30B 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
O3 C31 C26 124.3(2) . . ?
O3 C31 C29 115.72(19) . . ?
C26 C31 C29 120.01(18) . . ?
O2 C32 H32A 109.5 . . ?
O2 C32 H32B 109.5 . . ?
O2 C32 H32C 109.5 . . ?
H32A C32 H32B 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C27 C33 C28 120.9(2) . . ?
C27 C33 H33 119.5 . . ?
C28 C33 H33 119.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C3 C6 C10 -2.4(2) . . . . ?
O1 C3 C6 C12 176.94(15) . . . . ?
O2 C28 C33 C27 179.3(3) . . . . ?
N1 C1 C4 C2 144.36(16) . . . . ?
N1 C1 C4 C9 -101.18(18) . . . . ?
N1 C1 C4 C14 23.7(2) . . . . ?
N1 C3 C6 C10 174.99(14) . . . . ?
N1 C3 C6 C12 -5.7(2) . . . . ?
N2 C1 C4 C2 -31.63(14) . . . . ?
N2 C1 C4 C9 82.83(14) . . . . ?
N2 C1 C4 C14 -152.28(13) . . . . ?
N2 C5 C7 C8 62.10(15) . . . . ?
N2 C5 C7 C11 -63.25(16) . . . . ?
N2 C5 C15 C17 9.40(16) . . . . ?
N2 C5 C15 C18 -177.84(17) . . . . ?
N2 C12 C17 C15 7.07(17) . . . . ?
N2 C12 C17 C16 -177.08(17) . . . . ?
C1 N1 C3 O1 -174.39(15) . . . . ?
C1 N1 C3 C6 8.2(2) . . . . ?
C1 N2 C5 C2 23.02(16) . . . . ?
C1 N2 C5 C7 -91.15(15) . . . . ?
C1 N2 C5 C15 152.40(13) . . . . ?
C1 N2 C12 C6 16.1(2) . . . . ?
C1 N2 C12 C17 -156.60(14) . . . . ?
C1 C4 C9 N3 103.96(15) . . . . ?
C1 C4 C9 C8 -71.50(17) . . . . ?
C2 C4 C9 N3 -147.10(13) . . . . ?
C2 C4 C9 C8 37.45(18) . . . . ?
C2 C5 C7 C8 -46.52(16) . . . . ?
C2 C5 C7 C11 -171.87(12) . . . . ?
C2 C5 C15 C17 119.58(15) . . . . ?
C2 C5 C15 C18 -67.7(2) . . . . ?
C2 C20 C27 C33 176.5(2) . . . . ?
C3 N1 C1 N2 1.3(2) . . . . ?
C3 N1 C1 C4 -173.97(15) . . . . ?
C3 C6 C12 N2 -5.9(2) . . . . ?
C3 C6 C12 C17 163.29(17) . . . . ?
C4 C2 C5 N2 -39.28(13) . . . . ?
C4 C2 C5 C7 75.39(13) . . . . ?
C4 C2 C5 C15 -149.08(14) . . . . ?
C4 C2 C20 C13 74.50(19) . . . . ?
C4 C2 C20 C27 -103.01(19) . . . . ?
C5 N2 C1 N1 -170.37(14) . . . . ?
C5 N2 C1 C4 5.96(17) . . . . ?
C5 N2 C12 C6 171.89(13) . . . . ?
C5 N2 C12 C17 -0.81(17) . . . . ?
C5 C2 C4 C1 43.60(13) . . . . ?
C5 C2 C4 C9 -70.03(13) . . . . ?
C5 C2 C4 C14 163.55(12) . . . . ?
C5 C2 C20 C13 -38.8(2) . . . . ?
C5 C2 C20 C27 143.71(17) . . . . ?
C5 C7 C8 C9 8.6(2) . . . . ?
C5 C7 C8 C21 -167.39(14) . . . . ?
C5 C7 C11 C24 -101.32(19) . . . . ?
C5 C7 C11 C25 77.9(2) . . . . ?
C5 C15 C17 C12 -10.64(18) . . . . ?
C5 C15 C17 C16 173.04(15) . . . . ?
C5 C15 C18 C19 -171.89(17) . . . . ?
C6 C12 C17 C15 -162.83(19) . . . . ?
C6 C12 C17 C16 13.0(3) . . . . ?
C7 C5 C15 C17 -105.74(15) . . . . ?
C7 C5 C15 C18 67.0(2) . . . . ?
C7 C8 C9 N3 -179.85(15) . . . . ?
C7 C8 C9 C4 -4.8(2) . . . . ?
C7 C11 C24 C26 178.2(2) . . . . ?
C7 C11 C25 C29 -177.94(19) . . . . ?
C8 C7 C11 C24 133.93(17) . . . . ?
C8 C7 C11 C25 -46.8(2) . . . . ?
C10 C6 C12 N2 173.37(14) . . . . ?
C10 C6 C12 C17 -17.4(3) . . . . ?
C11 C7 C8 C9 134.71(16) . . . . ?
C11 C7 C8 C21 -41.30(19) . . . . ?
C11 C24 C26 C31 -0.2(4) . . . . ?
C11 C25 C29 C31 -0.3(4) . . . . ?
C12 N2 C1 N1 -14.6(2) . . . . ?
C12 N2 C1 C4 161.75(13) . . . . ?
C12 N2 C5 C2 -134.55(13) . . . . ?
C12 N2 C5 C7 111.28(14) . . . . ?
C12 N2 C5 C15 -5.17(17) . . . . ?
C13 C20 C27 C33 -1.2(3) . . . . ?
C13 C22 C28 O2 180.0(2) . . . . ?
C13 C22 C28 C33 -0.1(3) . . . . ?
C14 C4 C9 N3 -20.5(2) . . . . ?
C14 C4 C9 C8 164.02(14) . . . . ?
C15 C5 C7 C8 170.94(12) . . . . ?
C15 C5 C7 C11 45.59(16) . . . . ?
C15 C18 C19 C23 0.5(3) . . . . ?
C17 C15 C18 C19 0.2(3) . . . . ?
C17 C16 C23 C19 0.6(3) . . . . ?
C18 C15 C17 C12 175.85(16) . . . . ?
C18 C15 C17 C16 -0.5(3) . . . . ?
C18 C19 C23 C16 -0.9(3) . . . . ?
C20 C2 C4 C1 -81.64(14) . . . . ?
C20 C2 C4 C9 164.73(12) . . . . ?
C20 C2 C4 C14 38.32(17) . . . . ?
C20 C2 C5 N2 82.20(15) . . . . ?
C20 C2 C5 C7 -163.13(13) . . . . ?
C20 C2 C5 C15 -27.6(2) . . . . ?
C20 C13 C22 C28 0.2(3) . . . . ?
C20 C27 C33 C28 1.3(4) . . . . ?
C21 C8 C9 N3 -4.0(2) . . . . ?
C21 C8 C9 C4 171.04(14) . . . . ?
C22 C13 C20 C2 -177.06(15) . . . . ?
C22 C13 C20 C27 0.5(3) . . . . ?
C22 C28 C33 C27 -0.7(4) . . . . ?
C23 C16 C17 C12 -175.35(17) . . . . ?
C23 C16 C17 C15 0.1(3) . . . . ?
C24 C11 C25 C29 1.3(3) . . . . ?
C24 C26 C31 O3 -178.9(3) . . . . ?
C24 C26 C31 C29 1.3(4) . . . . ?
C25 C11 C24 C26 -1.1(3) . . . . ?
C25 C29 C31 O3 179.1(2) . . . . ?
C25 C29 C31 C26 -1.0(4) . . . . ?
C30 O3 C31 C26 -9.2(5) . . . . ?
C30 O3 C31 C29 170.6(3) . . . . ?
C32 O2 C28 C22 6.4(4) . . . . ?
C32 O2 C28 C33 -173.6(3) . . . . ?

_olex2_submission_original_sample_id GV-NN-01
_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_gv-mna

_database_code_depnum_ccdc_archive 'CCDC 2212407'
loop_
_audit_author_name
_audit_author_address
'Govindarajan R'
;Pondicherry university
India
;
_audit_update_record             
;
2025-12-28 deposited with the CCDC.	2026-02-19 downloaded from the CCDC.
;
_audit_creation_date             2022-10-08
_audit_creation_method           
;
Olex2 1.2-ac21
(compiled 2015.09.16 svn.r134, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        GV-MNA
_chemical_formula_moiety         'C11 H9 N3 O'
_chemical_formula_sum            'C11 H9 N3 O'
_chemical_formula_weight         199.21
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C18 H18 O2 N2 S4'
_chemical_oxdiff_usercomment     'YELLOW COLOUR BLOCK, 297K, 0.68 0.48 0.32'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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'

_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                   7.3731(5)
_cell_length_b                   7.4734(6)
_cell_length_c                   9.4400(9)
_cell_angle_alpha                113.196(8)
_cell_angle_beta                 90.392(7)
_cell_angle_gamma                100.287(6)
_cell_volume                     468.71(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2318
_cell_measurement_temperature    297
_cell_measurement_theta_max      29.2254
_cell_measurement_theta_min      3.5093
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61663
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.412
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             208
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0166
_diffrn_reflns_av_unetI/netI     0.0187
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.853
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            5180
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.853
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.290
_diffrn_reflns_theta_min         3.516
_diffrn_ambient_temperature      297
_diffrn_detector_area_resol_mean 15.9821
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.853
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -15.00   52.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.1835   57.0000 -120.0000 67

#__ type_ start__ end____ width___ exp.time_
  2 omega  -25.00   18.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.1835  -99.0000  -90.0000 43

#__ type_ start__ end____ width___ exp.time_
  3 omega    6.00   43.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       19.9960   57.0000  150.0000 37

#__ type_ start__ end____ width___ exp.time_
  4 omega   66.00   93.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       19.9960  178.0000  -90.0000 27

#__ type_ start__ end____ width___ exp.time_
  5 omega  -34.00   87.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       19.9960    0.0000 -120.0000 121

#__ type_ start__ end____ width___ exp.time_
  6 omega  -10.00   49.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -       19.9960  -77.0000   30.0000 59

#__ type_ start__ end____ width___ exp.time_
  7 omega  -25.00   25.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.1835  -99.0000   30.0000 50

#__ type_ start__ end____ width___ exp.time_
  8 omega  -90.00  -65.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.1835  -37.0000  150.0000 25

#__ type_ start__ end____ width___ exp.time_
  9 omega  -90.00   27.00   1.0000    4.0000
omega____ theta____ kappa____ phi______ frames
    -      -17.1835  -19.0000 -120.0000 117
;
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0299044000
_diffrn_orient_matrix_UB_12      0.1041847000
_diffrn_orient_matrix_UB_13      0.0397988000
_diffrn_orient_matrix_UB_21      0.0197259000
_diffrn_orient_matrix_UB_22      0.0076538000
_diffrn_orient_matrix_UB_23      -0.0710684000
_diffrn_orient_matrix_UB_31      -0.0913586000
_diffrn_orient_matrix_UB_32      0.0134417000
_diffrn_orient_matrix_UB_33      -0.0098393000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1882
_reflns_number_total             2186
_reflns_odcompleteness_completeness 99.69
_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, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.222
_refine_diff_density_min         -0.335
_refine_diff_density_rms         0.103
_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     136
_refine_ls_number_reflns         2186
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0537
_refine_ls_R_factor_gt           0.0463
_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)+(0.0629P)²+0.1119P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1169
_refine_ls_wR_factor_ref         0.1244
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups, All N(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C9(H9A,H9B)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), N1(H1), C7(H7), C4(H4), C5(H5)
2.c X=CH2 refined with riding coordinates:
 N15(H15A,H15B)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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
O12 O 0.89590(16) 0.13092(14) 0.17836(11) 0.0444(3) Uani 1 1 d . . . . .
C10 C 0.81267(17) -0.05610(18) 0.32800(14) 0.0290(3) Uani 1 1 d . . . . .
C3 C 0.71797(16) 0.10494(18) 0.60588(13) 0.0286(3) Uani 1 1 d . . . . .
C2 C 0.77245(16) 0.10163(18) 0.45472(13) 0.0276(3) Uani 1 1 d . . . . .
C8 C 0.69581(17) 0.29682(19) 0.69666(15) 0.0325(3) Uani 1 1 d . . . . .
C6 C 0.6236(2) 0.2023(3) 0.90566(17) 0.0479(4) Uani 1 1 d . . . . .
H6 H 0.5930 0.2338 1.0069 0.057 Uiso 1 1 calc R . . . .
N1 N 0.77857(16) 0.28362(16) 0.46047(12) 0.0351(3) Uani 1 1 d . . . . .
H1 H 0.8071 0.3155 0.3842 0.042 Uiso 1 1 calc R . . . .
N15 N 0.90806(17) -0.19376(17) 0.07059(13) 0.0415(3) Uani 1 1 d . . . . .
H15A H 0.9444 -0.1852 -0.0133 0.050 Uiso 1 1 calc R . . . .
H15B H 0.8929 -0.3058 0.0791 0.050 Uiso 1 1 calc R . . . .
C13 C 0.79512(19) -0.24652(19) 0.33035(15) 0.0348(3) Uani 1 1 d . . . . .
N14 N 0.7836(2) -0.40433(19) 0.32427(16) 0.0548(4) Uani 1 1 d . . . . .
C11 C 0.87487(17) -0.03209(18) 0.18838(14) 0.0311(3) Uani 1 1 d . . . . .
C7 C 0.6477(2) 0.3468(2) 0.84756(16) 0.0421(3) Uani 1 1 d . . . . .
H7 H 0.6320 0.4749 0.9080 0.051 Uiso 1 1 calc R . . . .
C9 C 0.7329(2) 0.42322(19) 0.60663(16) 0.0385(3) Uani 1 1 d . . . . .
H9A H 0.6244 0.4735 0.5932 0.046 Uiso 1 1 calc R . . . .
H9B H 0.8354 0.5338 0.6561 0.046 Uiso 1 1 calc R . . . .
C4 C 0.69097(19) -0.0409(2) 0.66443(16) 0.0371(3) Uani 1 1 d . . . . .
H4 H 0.7038 -0.1699 0.6038 0.045 Uiso 1 1 calc R . . . .
C5 C 0.6444(2) 0.0111(3) 0.81542(18) 0.0468(4) Uani 1 1 d . . . . .
H5 H 0.6269 -0.0842 0.8568 0.056 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
O12 C11 1.2412(15) . ?
C10 C2 1.3883(17) . ?
C10 C13 1.4148(17) . ?
C10 C11 1.4646(16) . ?
C3 C2 1.4770(16) . ?
C3 C8 1.3910(17) . ?
C3 C4 1.3897(17) . ?
C2 N1 1.3322(15) . ?
C8 C7 1.3892(18) . ?
C8 C9 1.4942(18) . ?
C6 H6 0.9300 . ?
C6 C7 1.378(2) . ?
C6 C5 1.383(2) . ?
N1 H1 0.8600 . ?
N1 C9 1.4504(16) . ?
N15 H15A 0.8600 . ?
N15 H15B 0.8600 . ?
N15 C11 1.3442(16) . ?
C13 N14 1.1455(17) . ?
C7 H7 0.9300 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C4 H4 0.9300 . ?
C4 C5 1.385(2) . ?
C5 H5 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
C2 C10 C13 120.58(11) . . ?
C2 C10 C11 121.66(11) . . ?
C13 C10 C11 117.75(11) . . ?
C8 C3 C2 107.48(11) . . ?
C4 C3 C2 132.06(12) . . ?
C4 C3 C8 120.46(12) . . ?
C10 C2 C3 128.38(11) . . ?
N1 C2 C10 124.63(11) . . ?
N1 C2 C3 106.99(10) . . ?
C3 C8 C9 109.62(11) . . ?
C7 C8 C3 120.79(13) . . ?
C7 C8 C9 129.59(12) . . ?
C7 C6 H6 119.6 . . ?
C7 C6 C5 120.88(13) . . ?
C5 C6 H6 119.6 . . ?
C2 N1 H1 122.9 . . ?
C2 N1 C9 114.14(11) . . ?
C9 N1 H1 122.9 . . ?
H15A N15 H15B 120.0 . . ?
C11 N15 H15A 120.0 . . ?
C11 N15 H15B 120.0 . . ?
N14 C13 C10 176.32(14) . . ?
O12 C11 C10 121.52(11) . . ?
O12 C11 N15 120.98(11) . . ?
N15 C11 C10 117.50(11) . . ?
C8 C7 H7 120.8 . . ?
C6 C7 C8 118.47(13) . . ?
C6 C7 H7 120.8 . . ?
C8 C9 H9A 111.4 . . ?
C8 C9 H9B 111.4 . . ?
N1 C9 C8 101.77(10) . . ?
N1 C9 H9A 111.4 . . ?
N1 C9 H9B 111.4 . . ?
H9A C9 H9B 109.3 . . ?
C3 C4 H4 120.9 . . ?
C5 C4 C3 118.22(13) . . ?
C5 C4 H4 120.9 . . ?
C6 C5 C4 121.17(14) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?

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
C10 C2 N1 C9 -179.22(12) . . . . ?
C3 C2 N1 C9 0.25(15) . . . . ?
C3 C8 C7 C6 0.5(2) . . . . ?
C3 C8 C9 N1 -0.54(14) . . . . ?
C3 C4 C5 C6 0.6(2) . . . . ?
C2 C10 C11 O12 0.7(2) . . . . ?
C2 C10 C11 N15 -179.07(11) . . . . ?
C2 C3 C8 C7 -178.81(11) . . . . ?
C2 C3 C8 C9 0.70(14) . . . . ?
C2 C3 C4 C5 178.09(13) . . . . ?
C2 N1 C9 C8 0.16(15) . . . . ?
C8 C3 C2 C10 178.85(12) . . . . ?
C8 C3 C2 N1 -0.59(14) . . . . ?
C8 C3 C4 C5 -0.9(2) . . . . ?
C13 C10 C2 C3 3.2(2) . . . . ?
C13 C10 C2 N1 -177.42(12) . . . . ?
C13 C10 C11 O12 -179.06(12) . . . . ?
C13 C10 C11 N15 1.14(18) . . . . ?
C11 C10 C2 C3 -176.57(11) . . . . ?
C11 C10 C2 N1 2.8(2) . . . . ?
C7 C8 C9 N1 178.91(13) . . . . ?
C7 C6 C5 C4 0.4(2) . . . . ?
C9 C8 C7 C6 -178.94(14) . . . . ?
C4 C3 C2 C10 -0.3(2) . . . . ?
C4 C3 C2 N1 -179.73(13) . . . . ?
C4 C3 C8 C7 0.45(19) . . . . ?
C4 C3 C8 C9 179.96(12) . . . . ?
C5 C6 C7 C8 -0.9(2) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_date_sample_data_collection 2019-01-29
_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_mnbf

_database_code_depnum_ccdc_archive 'CCDC 2212386'
loop_
_audit_author_name
_audit_author_address
'Govindarajan R'
;Pondicherry university
India
;
_audit_update_record             
;
2025-12-28 deposited with the CCDC.	2026-02-19 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT097_mnbf                
;
PROBLEM: Large Reported Max. (Positive) Residual Density 0.98 eA-3
RESPONSE: The residual density peak is located near [describe 
 location,  e.g., the O3 atom]. It was investigated but 
 could not be modeled as a chemically significant atom. 
 It likely represents minor unresolvable disorder or electronic 
 noise and does not affect the overall structural integrity.
;
_vrf_PLAT910_mnbf                
;
PROBLEM: Missing FCF Reflection(s) Below Theta(Min)[Deg]= 3.03 Note
RESPONSE: These low-angle reflections were physically 
 obscured by the  beamstop during data collection due to the
 experimental geometry. Their absence does not impact the 
 final structural model or the  reliability of the refinement.
;
_audit_creation_date             2022-10-12
_audit_creation_method           
;
Olex2 1.2-ac21
(compiled 2015.09.16 svn.r134, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        MNBF
_chemical_formula_moiety         'C36 H18 F6 N8 O, C5 H11 N, 2(C3 H7 N O)'
_chemical_formula_sum            'C47 H43 F6 N11 O3'
_chemical_formula_weight         923.92
_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                   13.9052(8)
_cell_length_b                   13.9260(9)
_cell_length_c                   14.7055(13)
_cell_angle_alpha                117.811(2)
_cell_angle_beta                 105.207(3)
_cell_angle_gamma                99.479(2)
_cell_volume                     2288.9(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9654
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      30.413
_cell_measurement_theta_min      2.971
_shelx_estimated_absorpt_T_max   0.985
_shelx_estimated_absorpt_T_min   0.980
_exptl_absorpt_coefficient_mu    0.104
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.7135
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0838 before and 0.0583 after correction.
The Ratio of minimum to maximum transmission is 0.9563.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'metallic light yellow'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.341
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             960
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0376
_diffrn_reflns_av_unetI/netI     0.0172
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            91057
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         3.028
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'four-circle diffractometer'
_diffrn_measurement_method       'Xcalibur, Eos'
_diffrn_radiation_type           MoK\a
_diffrn_standards_number         3
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        1.2
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6381
_reflns_number_total             8049
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.980
_refine_diff_density_min         -0.476
_refine_diff_density_rms         0.064
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     677
_refine_ls_number_reflns         8049
_refine_ls_number_restraints     258
_refine_ls_R_factor_all          0.0857
_refine_ls_R_factor_gt           0.0693
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.030
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1266P)²+2.0091P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1979
_refine_ls_wR_factor_ref         0.2226
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N8-H8A = N8-H8B = N7-H7A = N7-H7B
 0.85 with sigma of 0.02
 H8A-H8B = H7A-H7B
 1.38 with sigma of 0.02
 C36-F1 \\sim C36-F2 \\sim C36-F3 \\sim C36-F1' \\sim C36-F2' \\sim C36-F3'
 with sigma of 0.02
 C29-F4 \\sim C29-F5 \\sim C29-F6 \\sim C29-F4' \\sim C29-F5' \\sim C29-F6'
 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
C36 \\sim F1 \\sim F2 \\sim F3 \\sim F1' \\sim F2' \\sim F3': within 2A with
sigma of 0.02 and sigma for terminal atoms of 0.04
C29 \\sim F4 \\sim F5 \\sim F6 \\sim F4' \\sim F5' \\sim F6': within 2A with
sigma of 0.02 and sigma for terminal atoms of 0.04
Uanis(F4) \\sim Ueq, Uanis(F5) \\sim Ueq, Uanis(F6) \\sim Ueq, Uanis(F4') \\sim
Ueq, Uanis(F5') \\sim Ueq, Uanis(F6') \\sim Ueq: with sigma of 0.02 and sigma
for terminal atoms of 0.04
Uanis(F1) \\sim Ueq, Uanis(F2) \\sim Ueq, Uanis(F3) \\sim Ueq, Uanis(F1') \\sim
Ueq, Uanis(F2') \\sim Ueq, Uanis(F3') \\sim Ueq: with sigma of 0.02 and sigma
for terminal atoms of 0.04
4. Others
 Sof(F1')=Sof(F2')=Sof(F3')=1-FVAR(1)
 Sof(F1)=Sof(F2)=Sof(F3)=FVAR(1)
 Sof(F4')=Sof(F5')=Sof(F6')=1-FVAR(2)
 Sof(F4)=Sof(F5)=Sof(F6)=FVAR(2)
5.a Ternary CH refined with riding coordinates:
 C12(H12), C16(H16)
5.b Secondary CH2 refined with riding coordinates:
 C38(H38A,H38B), C39(H39A,H39B), C40(H40A,H40B), C41(H41A,H41B), C42(H42A,H42B)
5.c Me refined with riding coordinates:
 C44(H44A,H44B,H44C), C45(H45A,H45B,H45C), C47(H47A,H47B,H47C), C48(H48A,H48B,
 H48C)
5.d Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C9(H9), C24(H24), C25(H25), C27(H27), C28(H28),
 C31(H31), C32(H32), C34(H34), C35(H35), C43(H43), C46(H46)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_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
C1 C 0.1935(2) 0.3560(2) 0.2554(2) 0.0419(6) Uani 1 1 d . . . . .
C2 C 0.1713(2) 0.3868(2) 0.1720(2) 0.0393(6) Uani 1 1 d . . . . .
C3 C 0.21075(19) 0.4990(2) 0.2057(2) 0.0333(5) Uani 1 1 d . . . . .
C4 C 0.31513(19) 0.54301(19) 0.3874(2) 0.0316(5) Uani 1 1 d . . . . .
C5 C 0.19133(19) 0.5577(2) 0.1465(2) 0.0347(5) Uani 1 1 d . . . . .
C6 C 0.1349(2) 0.5159(2) 0.0350(2) 0.0480(7) Uani 1 1 d . . . . .
H6 H 0.1035 0.4371 -0.0174 0.058 Uiso 1 1 calc R . . . .
C7 C 0.1268(3) 0.5949(3) 0.0043(2) 0.0547(8) Uani 1 1 d . . . . .
H7 H 0.0893 0.5689 -0.0700 0.066 Uiso 1 1 calc R . . . .
C8 C 0.1735(3) 0.7117(3) 0.0818(2) 0.0524(7) Uani 1 1 d . . . . .
H8 H 0.1665 0.7632 0.0590 0.063 Uiso 1 1 calc R . . . .
C9 C 0.2303(2) 0.7537(2) 0.1926(2) 0.0431(6) Uani 1 1 d . . . . .
H9 H 0.2622 0.8326 0.2445 0.052 Uiso 1 1 calc R . . . .
C10 C 0.23863(19) 0.6754(2) 0.2243(2) 0.0333(5) Uani 1 1 d . . . . .
C11 C 0.29365(19) 0.70003(19) 0.34030(19) 0.0306(5) Uani 1 1 d . . . . .
C12 C 0.40968(19) 0.77541(18) 0.39026(19) 0.0305(5) Uani 1 1 d . . . . .
H12 H 0.4070 0.8478 0.3959 0.037 Uiso 1 1 calc R . . . .
C13 C 0.46877(19) 0.81027(19) 0.51240(19) 0.0317(5) Uani 1 1 d . . . . .
C14 C 0.4095(2) 0.8629(2) 0.5867(2) 0.0354(6) Uani 1 1 d . . . . .
C15 C 0.3035(2) 0.8375(2) 0.5397(2) 0.0402(6) Uani 1 1 d . . . . .
C16 C 0.2359(2) 0.7662(2) 0.4152(2) 0.0359(5) Uani 1 1 d . . . . .
H16 H 0.2206 0.8215 0.3950 0.043 Uiso 1 1 calc R . . . .
C18 C 0.4027(2) 0.6125(2) 0.4892(2) 0.0327(5) Uani 1 1 d . . . . .
C19 C 0.4218(2) 0.5627(2) 0.5551(2) 0.0362(6) Uani 1 1 d . . . . .
C20 C 0.5699(2) 0.9002(2) 0.5522(2) 0.0352(6) Uani 1 1 d . . . . .
C21 C 0.2508(3) 0.8893(3) 0.6108(3) 0.0597(8) Uani 1 1 d . . . . .
C22 C 0.1058(2) 0.2986(2) 0.0583(3) 0.0536(8) Uani 1 1 d . . . . .
C23 C 0.1296(2) 0.6867(2) 0.3866(2) 0.0415(6) Uani 1 1 d . . . . .
C24 C 0.1218(3) 0.6172(3) 0.4297(3) 0.0530(7) Uani 1 1 d . . . . .
H24 H 0.1819 0.6224 0.4807 0.064 Uiso 1 1 calc R . . . .
C25 C 0.0237(3) 0.5396(3) 0.3966(3) 0.0668(9) Uani 1 1 d . . . . .
H25 H 0.0188 0.4905 0.4228 0.080 Uiso 1 1 calc R . . . .
C26 C -0.0664(3) 0.5355(3) 0.3248(3) 0.0658(10) Uani 1 1 d . . . . .
C27 C -0.0591(3) 0.6055(3) 0.2841(3) 0.0640(9) Uani 1 1 d . . . . .
H27 H -0.1199 0.6027 0.2361 0.077 Uiso 1 1 calc R . . . .
C28 C 0.0380(2) 0.6804(3) 0.3140(3) 0.0520(7) Uani 1 1 d . . . . .
H28 H 0.0423 0.7272 0.2853 0.062 Uiso 1 1 calc R . . . .
C30 C 0.47082(19) 0.7314(2) 0.31692(19) 0.0330(5) Uani 1 1 d . . . . .
C31 C 0.4972(2) 0.6325(2) 0.2925(2) 0.0378(6) Uani 1 1 d . . . . .
H31 H 0.4759 0.5892 0.3208 0.045 Uiso 1 1 calc R . . . .
C32 C 0.5547(2) 0.5980(3) 0.2268(2) 0.0480(7) Uani 1 1 d . . . . .
H32 H 0.5720 0.5319 0.2112 0.058 Uiso 1 1 calc R . . . .
C33 C 0.5865(3) 0.6616(3) 0.1842(3) 0.0566(8) Uani 1 1 d . . . . .
C34 C 0.5615(3) 0.7605(3) 0.2085(3) 0.0672(10) Uani 1 1 d . . . . .
H34 H 0.5837 0.8042 0.1808 0.081 Uiso 1 1 calc R . . . .
C35 C 0.5040(3) 0.7943(3) 0.2737(3) 0.0535(8) Uani 1 1 d . . . . .
H35 H 0.4869 0.8606 0.2892 0.064 Uiso 1 1 calc R . . . .
N37 N 0.1848(2) 0.1631(2) 0.3534(2) 0.0625(7) Uani 1 1 d . . . . .
H37 H 0.176(3) 0.198(4) 0.316(3) 0.075 Uiso 1 1 d R . . . .
C38 C 0.1945(4) 0.2495(4) 0.4677(4) 0.0870(13) Uani 1 1 d . . . . .
H38A H 0.2600 0.3135 0.5042 0.104 Uiso 1 1 calc R . . . .
H38B H 0.1364 0.2794 0.4617 0.104 Uiso 1 1 calc R . . . .
C39 C 0.1936(4) 0.1997(5) 0.5366(4) 0.1073(17) Uani 1 1 d . . . . .
H39A H 0.1970 0.2575 0.6088 0.129 Uiso 1 1 calc R . . . .
H39B H 0.2552 0.1761 0.5486 0.129 Uiso 1 1 calc R . . . .
C40 C 0.0926(5) 0.0952(6) 0.4789(6) 0.125(2) Uani 1 1 d . . . . .
H40A H 0.0944 0.0607 0.5231 0.150 Uiso 1 1 calc R . . . .
H40B H 0.0311 0.1198 0.4725 0.150 Uiso 1 1 calc R . . . .
C41 C 0.0847(5) 0.0083(5) 0.3651(6) 0.1111(18) Uani 1 1 d . . . . .
H41A H 0.1427 -0.0215 0.3725 0.133 Uiso 1 1 calc R . . . .
H41B H 0.0190 -0.0557 0.3277 0.133 Uiso 1 1 calc R . . . .
C42 C 0.0880(5) 0.0583(4) 0.2963(4) 0.1038(17) Uani 1 1 d . . . . .
H42A H 0.0252 0.0793 0.2810 0.125 Uiso 1 1 calc R . . . .
H42B H 0.0874 0.0008 0.2255 0.125 Uiso 1 1 calc R . . . .
C43 C 0.3944(3) 1.1122(3) 0.9531(3) 0.0668(9) Uani 1 1 d . . . . .
H43 H 0.3257 1.0966 0.9080 0.080 Uiso 1 1 calc R . . . .
C44 C 0.3580(4) 1.2418(4) 1.1109(4) 0.0856(12) Uani 1 1 d . . . . .
H44A H 0.3957 1.2910 1.1903 0.128 Uiso 1 1 calc R . . . .
H44B H 0.3382 1.2873 1.0810 0.128 Uiso 1 1 calc R . . . .
H44C H 0.2956 1.1850 1.0942 0.128 Uiso 1 1 calc R . . . .
C45 C 0.5299(4) 1.2104(5) 1.1368(4) 0.1022(16) Uani 1 1 d . . . . .
H45A H 0.5396 1.2647 1.2120 0.153 Uiso 1 1 calc R . . . .
H45B H 0.5377 1.1406 1.1306 0.153 Uiso 1 1 calc R . . . .
H45C H 0.5820 1.2427 1.1177 0.153 Uiso 1 1 calc R . . . .
C46 C 0.7117(4) 1.0405(4) 0.9315(5) 0.0974(15) Uani 1 1 d . . . . .
H46 H 0.6579 1.0662 0.9499 0.117 Uiso 1 1 calc R . . . .
C47 C 0.8153(6) 1.1286(7) 1.1274(5) 0.151(3) Uani 1 1 d . . . . .
H47A H 0.8830 1.1337 1.1710 0.226 Uiso 1 1 calc R . . . .
H47B H 0.8142 1.2046 1.1480 0.226 Uiso 1 1 calc R . . . .
H47C H 0.7609 1.0917 1.1410 0.226 Uiso 1 1 calc R . . . .
C48 C 0.8807(4) 1.0176(6) 0.9911(5) 0.1131(17) Uani 1 1 d . . . . .
H48A H 0.9354 1.0446 1.0615 0.170 Uiso 1 1 calc R . . . .
H48B H 0.8536 0.9349 0.9485 0.170 Uiso 1 1 calc R . . . .
H48C H 0.9091 1.0440 0.9507 0.170 Uiso 1 1 calc R . . . .
N1 N 0.0549(3) 0.2253(2) -0.0316(3) 0.0838(11) Uani 1 1 d . . . . .
N2 N 0.26786(17) 0.43493(18) 0.35756(19) 0.0398(5) Uani 1 1 d . . . . .
N3 N 0.27776(15) 0.57990(16) 0.31548(16) 0.0303(4) Uani 1 1 d . . . . .
N4 N 0.4416(2) 0.5310(2) 0.6148(2) 0.0510(6) Uani 1 1 d . . . . .
N5 N 0.6424(2) 0.9719(2) 0.5759(2) 0.0495(6) Uani 1 1 d . . . . .
N6 N 0.2088(3) 0.9324(4) 0.6682(3) 0.1020(14) Uani 1 1 d . . . . .
N8 N 0.4697(2) 0.9302(2) 0.69658(18) 0.0469(6) Uani 1 1 d D . . . .
N9 N 0.4250(2) 1.1852(2) 1.0614(2) 0.0598(7) Uani 1 1 d . . . . .
N10 N 0.7966(2) 1.0616(3) 1.0099(2) 0.0643(7) Uani 1 1 d . . . . .
O1 O 0.14518(18) 0.25654(17) 0.2288(2) 0.0612(6) Uani 1 1 d . . . . .
C17 C 0.4912(2) 0.71370(19) 0.52854(19) 0.0322(5) Uani 1 1 d . . . . .
O2 O 0.4483(3) 1.0635(3) 0.9072(2) 0.0832(8) Uani 1 1 d . . . . .
O3 O 0.6995(3) 0.9845(3) 0.8281(3) 0.1094(12) Uani 1 1 d . . . . .
C36 C 0.6495(4) 0.6270(4) 0.1137(4) 0.0830(12) Uani 1 1 d D U . . .
F1 F 0.7376(17) 0.712(2) 0.152(2) 0.139(8) Uani 0.42(4) 1 d D U P A 1
F2 F 0.6834(18) 0.543(2) 0.110(2) 0.107(4) Uani 0.42(4) 1 d D U P A 1
F3 F 0.599(2) 0.601(2) 0.0103(11) 0.116(6) Uani 0.42(4) 1 d D U P A 1
F1' F 0.6384(18) 0.5143(9) 0.0659(15) 0.107(4) Uani 0.58(4) 1 d D U P A 2
F2' F 0.7512(7) 0.6884(15) 0.1706(16) 0.123(4) Uani 0.58(4) 1 d D U P A 2
F3' F 0.6200(15) 0.6393(18) 0.0278(12) 0.108(4) Uani 0.58(4) 1 d D U P A 2
C29 C -0.1729(4) 0.4545(4) 0.2912(5) 0.1006(16) Uani 1 1 d D U . . .
F4 F -0.1736(8) 0.3928(9) 0.3348(8) 0.131(4) Uani 0.620(11) 1 d D U P B 3
F5 F -0.2068(9) 0.3707(10) 0.1831(6) 0.137(4) Uani 0.620(11) 1 d D U P B 3
F6 F -0.2472(3) 0.5056(5) 0.2958(7) 0.124(3) Uani 0.620(11) 1 d D U P B 3
F4' F -0.1932(9) 0.4877(10) 0.3892(10) 0.146(6) Uani 0.380(11) 1 d D U P B 4
F5' F -0.1587(18) 0.3639(15) 0.297(2) 0.178(8) Uani 0.380(11) 1 d D U P B 4
F6' F -0.2359(12) 0.4040(19) 0.1918(13) 0.156(8) Uani 0.380(11) 1 d D U P B 4
N7 N 0.58696(19) 0.7357(2) 0.5860(2) 0.0452(6) Uani 1 1 d D . . . .
H7A H 0.597(2) 0.6815(19) 0.597(3) 0.054 Uiso 1 1 d DR . . . .
H7B H 0.631(2) 0.7980(16) 0.633(2) 0.054 Uiso 1 1 d DR . . . .
H8A H 0.5348(15) 0.940(3) 0.727(2) 0.052(9) Uiso 1 1 d D . . . .
H8B H 0.441(2) 0.956(3) 0.741(2) 0.062(10) Uiso 1 1 d 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 C2 1.456(4) . ?
C1 N2 1.343(4) . ?
C1 O1 1.254(3) . ?
C2 C3 1.357(3) . ?
C2 C22 1.432(4) . ?
C3 C5 1.453(3) . ?
C3 N3 1.383(3) . ?
C4 C18 1.402(3) . ?
C4 N2 1.341(3) . ?
C4 N3 1.399(3) . ?
C5 C6 1.388(4) . ?
C5 C10 1.388(3) . ?
C6 H6 0.9300 . ?
C6 C7 1.380(4) . ?
C7 H7 0.9300 . ?
C7 C8 1.379(4) . ?
C8 H8 0.9300 . ?
C8 C9 1.380(4) . ?
C9 H9 0.9300 . ?
C9 C10 1.381(4) . ?
C10 C11 1.516(3) . ?
C11 C12 1.532(3) . ?
C11 C16 1.570(3) . ?
C11 N3 1.499(3) . ?
C12 H12 0.9800 . ?
C12 C13 1.555(3) . ?
C12 C30 1.516(3) . ?
C13 C14 1.528(3) . ?
C13 C20 1.481(3) . ?
C13 C17 1.536(3) . ?
C14 C15 1.356(4) . ?
C14 N8 1.345(3) . ?
C15 C16 1.521(4) . ?
C15 C21 1.423(4) . ?
C16 H16 0.9800 . ?
C16 C23 1.513(4) . ?
C18 C19 1.430(3) . ?
C18 C17 1.459(3) . ?
C19 N4 1.147(3) . ?
C20 N5 1.138(3) . ?
C21 N6 1.147(4) . ?
C22 N1 1.142(4) . ?
C23 C24 1.387(4) . ?
C23 C28 1.390(4) . ?
C24 H24 0.9300 . ?
C24 C25 1.393(5) . ?
C25 H25 0.9300 . ?
C25 C26 1.383(6) . ?
C26 C27 1.365(6) . ?
C26 C29 1.501(6) . ?
C27 H27 0.9300 . ?
C27 C28 1.379(5) . ?
C28 H28 0.9300 . ?
C30 C31 1.391(3) . ?
C30 C35 1.387(4) . ?
C31 H31 0.9300 . ?
C31 C32 1.378(4) . ?
C32 H32 0.9300 . ?
C32 C33 1.381(4) . ?
C33 C34 1.383(5) . ?
C33 C36 1.492(5) . ?
C34 H34 0.9300 . ?
C34 C35 1.374(5) . ?
C35 H35 0.9300 . ?
N37 H37 0.88(4) . ?
N37 C38 1.494(5) . ?
N37 C42 1.505(5) . ?
C38 H38A 0.9700 . ?
C38 H38B 0.9700 . ?
C38 C39 1.472(7) . ?
C39 H39A 0.9700 . ?
C39 H39B 0.9700 . ?
C39 C40 1.536(8) . ?
C40 H40A 0.9700 . ?
C40 H40B 0.9700 . ?
C40 C41 1.499(8) . ?
C41 H41A 0.9700 . ?
C41 H41B 0.9700 . ?
C41 C42 1.476(7) . ?
C42 H42A 0.9700 . ?
C42 H42B 0.9700 . ?
C43 H43 0.9300 . ?
C43 N9 1.320(5) . ?
C43 O2 1.218(5) . ?
C44 H44A 0.9600 . ?
C44 H44B 0.9600 . ?
C44 H44C 0.9600 . ?
C44 N9 1.442(5) . ?
C45 H45A 0.9600 . ?
C45 H45B 0.9600 . ?
C45 H45C 0.9600 . ?
C45 N9 1.449(6) . ?
C46 H46 0.9300 . ?
C46 N10 1.291(6) . ?
C46 O3 1.289(7) . ?
C47 H47A 0.9600 . ?
C47 H47B 0.9600 . ?
C47 H47C 0.9600 . ?
C47 N10 1.451(7) . ?
C48 H48A 0.9600 . ?
C48 H48B 0.9600 . ?
C48 H48C 0.9600 . ?
C48 N10 1.437(6) . ?
N8 H8A 0.852(17) . ?
N8 H8B 0.828(17) . ?
C17 N7 1.271(3) . ?
C36 F1 1.327(12) . ?
C36 F2 1.318(11) . ?
C36 F3 1.333(12) . ?
C36 F1' 1.347(9) . ?
C36 F2' 1.321(10) . ?
C36 F3' 1.321(10) . ?
C29 F4 1.289(9) . ?
C29 F5 1.344(9) . ?
C29 F6 1.346(7) . ?
C29 F4' 1.416(10) . ?
C29 F5' 1.348(14) . ?
C29 F6' 1.251(12) . ?
N7 H7A 0.869(17) . ?
N7 H7B 0.805(17) . ?

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 C1 C2 118.2(2) . . ?
O1 C1 C2 119.3(2) . . ?
O1 C1 N2 122.5(3) . . ?
C3 C2 C1 118.6(2) . . ?
C3 C2 C22 122.3(3) . . ?
C22 C2 C1 119.0(2) . . ?
C2 C3 C5 131.2(2) . . ?
C2 C3 N3 120.0(2) . . ?
N3 C3 C5 108.7(2) . . ?
N2 C4 C18 117.2(2) . . ?
N2 C4 N3 119.4(2) . . ?
N3 C4 C18 123.4(2) . . ?
C6 C5 C3 131.5(2) . . ?
C6 C5 C10 120.8(2) . . ?
C10 C5 C3 107.7(2) . . ?
C5 C6 H6 121.0 . . ?
C7 C6 C5 117.9(3) . . ?
C7 C6 H6 121.0 . . ?
C6 C7 H7 119.5 . . ?
C8 C7 C6 121.1(3) . . ?
C8 C7 H7 119.5 . . ?
C7 C8 H8 119.4 . . ?
C7 C8 C9 121.2(3) . . ?
C9 C8 H8 119.4 . . ?
C8 C9 H9 120.9 . . ?
C8 C9 C10 118.1(2) . . ?
C10 C9 H9 120.9 . . ?
C5 C10 C11 111.2(2) . . ?
C9 C10 C5 120.8(2) . . ?
C9 C10 C11 128.0(2) . . ?
C10 C11 C12 110.20(19) . . ?
C10 C11 C16 108.08(19) . . ?
C12 C11 C16 109.21(18) . . ?
N3 C11 C10 100.66(17) . . ?
N3 C11 C12 114.42(18) . . ?
N3 C11 C16 113.80(19) . . ?
C11 C12 H12 104.8 . . ?
C11 C12 C13 112.70(19) . . ?
C13 C12 H12 104.8 . . ?
C30 C12 C11 115.04(19) . . ?
C30 C12 H12 104.8 . . ?
C30 C12 C13 113.28(19) . . ?
C14 C13 C12 112.23(19) . . ?
C14 C13 C17 105.73(19) . . ?
C20 C13 C12 104.15(19) . . ?
C20 C13 C14 108.47(19) . . ?
C20 C13 C17 109.69(19) . . ?
C17 C13 C12 116.40(18) . . ?
C15 C14 C13 119.4(2) . . ?
N8 C14 C13 114.9(2) . . ?
N8 C14 C15 125.6(2) . . ?
C14 C15 C16 125.8(2) . . ?
C14 C15 C21 118.1(2) . . ?
C21 C15 C16 115.9(2) . . ?
C11 C16 H16 105.8 . . ?
C15 C16 C11 114.3(2) . . ?
C15 C16 H16 105.8 . . ?
C23 C16 C11 111.49(19) . . ?
C23 C16 C15 112.8(2) . . ?
C23 C16 H16 105.8 . . ?
C4 C18 C19 114.6(2) . . ?
C4 C18 C17 130.7(2) . . ?
C19 C18 C17 113.0(2) . . ?
N4 C19 C18 174.8(3) . . ?
N5 C20 C13 173.3(3) . . ?
N6 C21 C15 179.1(5) . . ?
N1 C22 C2 177.3(3) . . ?
C24 C23 C16 121.1(3) . . ?
C24 C23 C28 118.9(3) . . ?
C28 C23 C16 120.0(3) . . ?
C23 C24 H24 120.1 . . ?
C23 C24 C25 119.9(3) . . ?
C25 C24 H24 120.1 . . ?
C24 C25 H25 120.0 . . ?
C26 C25 C24 120.0(3) . . ?
C26 C25 H25 120.0 . . ?
C25 C26 C29 120.4(4) . . ?
C27 C26 C25 120.1(3) . . ?
C27 C26 C29 119.4(4) . . ?
C26 C27 H27 119.9 . . ?
C26 C27 C28 120.2(3) . . ?
C28 C27 H27 119.9 . . ?
C23 C28 H28 119.6 . . ?
C27 C28 C23 120.8(3) . . ?
C27 C28 H28 119.6 . . ?
C31 C30 C12 123.4(2) . . ?
C35 C30 C12 118.2(2) . . ?
C35 C30 C31 118.3(2) . . ?
C30 C31 H31 119.7 . . ?
C32 C31 C30 120.7(2) . . ?
C32 C31 H31 119.7 . . ?
C31 C32 H32 119.9 . . ?
C31 C32 C33 120.1(3) . . ?
C33 C32 H32 119.9 . . ?
C32 C33 C34 119.8(3) . . ?
C32 C33 C36 121.4(3) . . ?
C34 C33 C36 118.8(3) . . ?
C33 C34 H34 120.1 . . ?
C35 C34 C33 119.9(3) . . ?
C35 C34 H34 120.1 . . ?
C30 C35 H35 119.4 . . ?
C34 C35 C30 121.2(3) . . ?
C34 C35 H35 119.4 . . ?
C38 N37 H37 105(3) . . ?
C38 N37 C42 111.1(3) . . ?
C42 N37 H37 108(3) . . ?
N37 C38 H38A 109.2 . . ?
N37 C38 H38B 109.2 . . ?
H38A C38 H38B 107.9 . . ?
C39 C38 N37 112.2(4) . . ?
C39 C38 H38A 109.2 . . ?
C39 C38 H38B 109.2 . . ?
C38 C39 H39A 109.6 . . ?
C38 C39 H39B 109.6 . . ?
C38 C39 C40 110.4(5) . . ?
H39A C39 H39B 108.1 . . ?
C40 C39 H39A 109.6 . . ?
C40 C39 H39B 109.6 . . ?
C39 C40 H40A 109.7 . . ?
C39 C40 H40B 109.7 . . ?
H40A C40 H40B 108.2 . . ?
C41 C40 C39 109.6(4) . . ?
C41 C40 H40A 109.7 . . ?
C41 C40 H40B 109.7 . . ?
C40 C41 H41A 109.2 . . ?
C40 C41 H41B 109.2 . . ?
H41A C41 H41B 107.9 . . ?
C42 C41 C40 112.0(5) . . ?
C42 C41 H41A 109.2 . . ?
C42 C41 H41B 109.2 . . ?
N37 C42 H42A 109.2 . . ?
N37 C42 H42B 109.2 . . ?
C41 C42 N37 111.9(4) . . ?
C41 C42 H42A 109.2 . . ?
C41 C42 H42B 109.2 . . ?
H42A C42 H42B 107.9 . . ?
N9 C43 H43 117.2 . . ?
O2 C43 H43 117.2 . . ?
O2 C43 N9 125.7(4) . . ?
H44A C44 H44B 109.5 . . ?
H44A C44 H44C 109.5 . . ?
H44B C44 H44C 109.5 . . ?
N9 C44 H44A 109.5 . . ?
N9 C44 H44B 109.5 . . ?
N9 C44 H44C 109.5 . . ?
H45A C45 H45B 109.5 . . ?
H45A C45 H45C 109.5 . . ?
H45B C45 H45C 109.5 . . ?
N9 C45 H45A 109.5 . . ?
N9 C45 H45B 109.5 . . ?
N9 C45 H45C 109.5 . . ?
N10 C46 H46 119.2 . . ?
O3 C46 H46 119.2 . . ?
O3 C46 N10 121.6(5) . . ?
H47A C47 H47B 109.5 . . ?
H47A C47 H47C 109.5 . . ?
H47B C47 H47C 109.5 . . ?
N10 C47 H47A 109.5 . . ?
N10 C47 H47B 109.5 . . ?
N10 C47 H47C 109.5 . . ?
H48A C48 H48B 109.5 . . ?
H48A C48 H48C 109.5 . . ?
H48B C48 H48C 109.5 . . ?
N10 C48 H48A 109.5 . . ?
N10 C48 H48B 109.5 . . ?
N10 C48 H48C 109.5 . . ?
C4 N2 C1 122.2(2) . . ?
C3 N3 C4 119.33(19) . . ?
C3 N3 C11 111.12(18) . . ?
C4 N3 C11 129.42(19) . . ?
C14 N8 H8A 126(2) . . ?
C14 N8 H8B 119(2) . . ?
H8A N8 H8B 115(3) . . ?
C43 N9 C44 123.2(4) . . ?
C43 N9 C45 119.9(3) . . ?
C44 N9 C45 116.9(3) . . ?
C46 N10 C47 123.3(5) . . ?
C46 N10 C48 124.2(4) . . ?
C48 N10 C47 112.5(5) . . ?
C18 C17 C13 119.2(2) . . ?
N7 C17 C13 115.1(2) . . ?
N7 C17 C18 125.4(2) . . ?
F1 C36 C33 112.0(12) . . ?
F1 C36 F3 103.8(15) . . ?
F2 C36 C33 114.3(8) . . ?
F2 C36 F1 103.7(13) . . ?
F2 C36 F3 109.5(13) . . ?
F3 C36 C33 112.7(12) . . ?
F1' C36 C33 112.4(7) . . ?
F2' C36 C33 112.1(9) . . ?
F2' C36 F1' 108.8(11) . . ?
F2' C36 F3' 105.9(11) . . ?
F3' C36 C33 113.5(8) . . ?
F3' C36 F1' 103.5(8) . . ?
F4 C29 C26 115.8(6) . . ?
F4 C29 F5 99.7(8) . . ?
F4 C29 F6 114.3(7) . . ?
F5 C29 C26 108.6(6) . . ?
F5 C29 F6 104.4(7) . . ?
F6 C29 C26 112.3(4) . . ?
F4' C29 C26 107.4(5) . . ?
F5' C29 C26 108.2(10) . . ?
F5' C29 F4' 84.6(10) . . ?
F6' C29 C26 117.5(11) . . ?
F6' C29 F4' 130.0(11) . . ?
F6' C29 F5' 100.6(15) . . ?
C17 N7 H7A 113(2) . . ?
C17 N7 H7B 128(2) . . ?
H7A N7 H7B 113(2) . . ?

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
C12 H12 N5 0.98 2.59 3.542(3) 164.7 2_676
C44 H44B F3' 0.96 2.40 3.210(14) 141.7 2_676
C47 H47B F5 0.96 2.21 3.167(16) 173.7 1_666
C47 H47B F5' 0.96 2.15 2.93(2) 137.7 1_666
N7 H7B O3 0.805(17) 2.58(2) 3.304(4) 150(3) .
N8 H8A O3 0.852(17) 2.176(19) 3.020(4) 171(3) .
N8 H8B O2 0.828(17) 2.15(2) 2.903(3) 151(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
C1 C2 C3 C5 -170.8(3) . . . . ?
C1 C2 C3 N3 5.4(4) . . . . ?
C2 C1 N2 C4 5.8(4) . . . . ?
C2 C3 C5 C6 -7.2(5) . . . . ?
C2 C3 C5 C10 170.7(3) . . . . ?
C2 C3 N3 C4 8.2(3) . . . . ?
C2 C3 N3 C11 -168.2(2) . . . . ?
C3 C5 C6 C7 177.2(3) . . . . ?
C3 C5 C10 C9 -177.9(2) . . . . ?
C3 C5 C10 C11 0.7(3) . . . . ?
C4 C18 C17 C13 47.0(4) . . . . ?
C4 C18 C17 N7 -140.3(3) . . . . ?
C5 C3 N3 C4 -174.8(2) . . . . ?
C5 C3 N3 C11 8.8(3) . . . . ?
C5 C6 C7 C8 0.1(5) . . . . ?
C5 C10 C11 C12 125.3(2) . . . . ?
C5 C10 C11 C16 -115.4(2) . . . . ?
C5 C10 C11 N3 4.1(3) . . . . ?
C6 C5 C10 C9 0.2(4) . . . . ?
C6 C5 C10 C11 178.9(2) . . . . ?
C6 C7 C8 C9 0.4(5) . . . . ?
C7 C8 C9 C10 -0.6(5) . . . . ?
C8 C9 C10 C5 0.3(4) . . . . ?
C8 C9 C10 C11 -178.1(3) . . . . ?
C9 C10 C11 C12 -56.2(3) . . . . ?
C9 C10 C11 C16 63.1(3) . . . . ?
C9 C10 C11 N3 -177.4(3) . . . . ?
C10 C5 C6 C7 -0.4(4) . . . . ?
C10 C11 C12 C13 176.35(18) . . . . ?
C10 C11 C12 C30 -51.7(2) . . . . ?
C10 C11 C16 C15 -157.0(2) . . . . ?
C10 C11 C16 C23 73.7(2) . . . . ?
C10 C11 N3 C3 -7.8(2) . . . . ?
C10 C11 N3 C4 176.3(2) . . . . ?
C11 C12 C13 C14 -51.6(2) . . . . ?
C11 C12 C13 C20 -168.70(18) . . . . ?
C11 C12 C13 C17 70.4(3) . . . . ?
C11 C12 C30 C31 -68.8(3) . . . . ?
C11 C12 C30 C35 112.5(3) . . . . ?
C11 C16 C23 C24 82.1(3) . . . . ?
C11 C16 C23 C28 -96.4(3) . . . . ?
C12 C11 C16 C15 -37.1(3) . . . . ?
C12 C11 C16 C23 -166.4(2) . . . . ?
C12 C11 N3 C3 -126.0(2) . . . . ?
C12 C11 N3 C4 58.1(3) . . . . ?
C12 C13 C14 C15 23.8(3) . . . . ?
C12 C13 C14 N8 -157.7(2) . . . . ?
C12 C13 C17 C18 -58.8(3) . . . . ?
C12 C13 C17 N7 127.8(2) . . . . ?
C12 C30 C31 C32 -178.8(2) . . . . ?
C12 C30 C35 C34 178.7(3) . . . . ?
C13 C12 C30 C31 62.9(3) . . . . ?
C13 C12 C30 C35 -115.8(3) . . . . ?
C13 C14 C15 C16 -4.8(4) . . . . ?
C13 C14 C15 C21 -179.0(3) . . . . ?
C14 C13 C17 C18 66.6(3) . . . . ?
C14 C13 C17 N7 -106.9(3) . . . . ?
C14 C15 C16 C11 11.8(4) . . . . ?
C14 C15 C16 C23 140.5(3) . . . . ?
C15 C16 C23 C24 -48.0(3) . . . . ?
C15 C16 C23 C28 133.5(3) . . . . ?
C16 C11 C12 C13 57.8(2) . . . . ?
C16 C11 C12 C30 -170.30(19) . . . . ?
C16 C11 N3 C3 107.5(2) . . . . ?
C16 C11 N3 C4 -68.4(3) . . . . ?
C16 C23 C24 C25 -176.0(3) . . . . ?
C16 C23 C28 C27 177.8(3) . . . . ?
C18 C4 N2 C1 -170.3(2) . . . . ?
C18 C4 N3 C3 162.9(2) . . . . ?
C18 C4 N3 C11 -21.5(4) . . . . ?
C19 C18 C17 C13 -148.9(2) . . . . ?
C19 C18 C17 N7 23.8(4) . . . . ?
C20 C13 C14 C15 138.3(2) . . . . ?
C20 C13 C14 N8 -43.2(3) . . . . ?
C20 C13 C17 C18 -176.7(2) . . . . ?
C20 C13 C17 N7 9.9(3) . . . . ?
C21 C15 C16 C11 -173.9(2) . . . . ?
C21 C15 C16 C23 -45.2(3) . . . . ?
C22 C2 C3 C5 6.9(5) . . . . ?
C22 C2 C3 N3 -176.9(3) . . . . ?
C23 C24 C25 C26 -2.9(5) . . . . ?
C24 C23 C28 C27 -0.7(4) . . . . ?
C24 C25 C26 C27 1.5(5) . . . . ?
C24 C25 C26 C29 -178.2(3) . . . . ?
C25 C26 C27 C28 0.3(5) . . . . ?
C25 C26 C29 F4 1.1(8) . . . . ?
C25 C26 C29 F5 -110.1(8) . . . . ?
C25 C26 C29 F6 134.9(6) . . . . ?
C25 C26 C29 F4' 62.8(9) . . . . ?
C25 C26 C29 F5' -27.2(12) . . . . ?
C25 C26 C29 F6' -140.1(13) . . . . ?
C26 C27 C28 C23 -0.7(5) . . . . ?
C27 C26 C29 F4 -178.6(7) . . . . ?
C27 C26 C29 F5 70.2(8) . . . . ?
C27 C26 C29 F6 -44.8(7) . . . . ?
C27 C26 C29 F4' -116.9(8) . . . . ?
C27 C26 C29 F5' 153.1(11) . . . . ?
C27 C26 C29 F6' 40.1(14) . . . . ?
C28 C23 C24 C25 2.5(4) . . . . ?
C30 C12 C13 C14 175.62(18) . . . . ?
C30 C12 C13 C20 58.5(2) . . . . ?
C30 C12 C13 C17 -62.4(3) . . . . ?
C30 C31 C32 C33 -0.1(4) . . . . ?
C31 C30 C35 C34 -0.1(5) . . . . ?
C31 C32 C33 C34 0.6(5) . . . . ?
C31 C32 C33 C36 179.5(3) . . . . ?
C32 C33 C34 C35 -0.9(6) . . . . ?
C32 C33 C36 F1 -126.6(19) . . . . ?
C32 C33 C36 F2 -9.0(15) . . . . ?
C32 C33 C36 F3 116.9(14) . . . . ?
C32 C33 C36 F1' 22.1(12) . . . . ?
C32 C33 C36 F2' -100.9(10) . . . . ?
C32 C33 C36 F3' 139.1(11) . . . . ?
C33 C34 C35 C30 0.6(6) . . . . ?
C34 C33 C36 F1 52(2) . . . . ?
C34 C33 C36 F2 169.9(14) . . . . ?
C34 C33 C36 F3 -64.3(14) . . . . ?
C34 C33 C36 F1' -159.1(11) . . . . ?
C34 C33 C36 F2' 78.0(10) . . . . ?
C34 C33 C36 F3' -42.0(12) . . . . ?
C35 C30 C31 C32 -0.1(4) . . . . ?
N37 C38 C39 C40 -56.7(6) . . . . ?
C38 N37 C42 C41 -53.4(6) . . . . ?
C38 C39 C40 C41 56.5(7) . . . . ?
C39 C40 C41 C42 -56.1(7) . . . . ?
C40 C41 C42 N37 55.1(7) . . . . ?
C42 N37 C38 C39 55.0(5) . . . . ?
N2 C1 C2 C3 -12.6(4) . . . . ?
N2 C1 C2 C22 169.7(3) . . . . ?
N2 C4 C18 C19 -7.7(3) . . . . ?
N2 C4 C18 C17 156.3(2) . . . . ?
N2 C4 N3 C3 -15.2(3) . . . . ?
N2 C4 N3 C11 160.4(2) . . . . ?
N3 C3 C5 C6 176.3(3) . . . . ?
N3 C3 C5 C10 -5.9(3) . . . . ?
N3 C4 C18 C19 174.3(2) . . . . ?
N3 C4 C18 C17 -21.8(4) . . . . ?
N3 C4 N2 C1 7.9(4) . . . . ?
N3 C11 C12 C13 -71.1(2) . . . . ?
N3 C11 C12 C30 60.8(3) . . . . ?
N3 C11 C16 C15 92.1(2) . . . . ?
N3 C11 C16 C23 -37.2(3) . . . . ?
N8 C14 C15 C16 176.9(2) . . . . ?
N8 C14 C15 C21 2.7(4) . . . . ?
O1 C1 C2 C3 169.5(3) . . . . ?
O1 C1 C2 C22 -8.2(4) . . . . ?
O1 C1 N2 C4 -176.3(3) . . . . ?
C17 C13 C14 C15 -104.1(3) . . . . ?
C17 C13 C14 N8 74.4(3) . . . . ?
O2 C43 N9 C44 178.9(4) . . . . ?
O2 C43 N9 C45 -2.0(6) . . . . ?
O3 C46 N10 C47 177.2(5) . . . . ?
O3 C46 N10 C48 -5.9(7) . . . . ?
C36 C33 C34 C35 -179.7(4) . . . . ?
C29 C26 C27 C28 -180.0(3) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_original_sample_id MNBF
_olex2_submission_special_instructions 'No special instructions were received'
