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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_OO_a
_database_code_depnum_ccdc_archive 'CCDC 1973970'
loop_
_audit_author_name
_audit_author_address
'ANOOP KUMAR PANDAY'
;Indian Institute of Technology Patna, Patna
India
;
_audit_update_record             
;
2019-12-24 deposited with the CCDC.	2020-06-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H19 N3 O6'
_chemical_formula_weight         457.43

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

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

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

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

_cell_length_a                   15.1872(9)
_cell_length_b                   16.3092(10)
_cell_length_c                   34.3428(19)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     8506.4(9)
_cell_formula_units_Z            16
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    9597
_cell_measurement_theta_min      2.554
_cell_measurement_theta_max      24.865

_exptl_crystal_description       needle
_exptl_crystal_colour            RED
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.429
_exptl_crystal_F_000             3808
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.104
_shelx_estimated_absorpt_T_min   0.969
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.985
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            143176
_diffrn_reflns_av_unetI/netI     0.1551
_diffrn_reflns_av_R_equivalents  0.3568
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -40
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_theta_min         2.554
_diffrn_reflns_theta_max         24.865
_diffrn_reflns_theta_full        24.865
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             7331
_reflns_number_gt                3054
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0680P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.00061(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         7331
_refine_ls_number_parameters     620
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2330
_refine_ls_R_factor_gt           0.0790
_refine_ls_wR_factor_ref         0.1657
_refine_ls_wR_factor_gt          0.1212
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_restrained_S_all      1.005
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.6261(3) 0.3282(3) 0.77577(11) 0.0329(11) Uani 1 1 d . . . . .
C2 C 0.6090(3) 0.2628(2) 0.74840(11) 0.0338(11) Uani 1 1 d . . . . .
C3 C 0.6094(3) 0.1790(2) 0.76592(11) 0.0314(11) Uani 1 1 d . . . . .
C4 C 0.5862(3) 0.1127(3) 0.74233(12) 0.0442(13) Uani 1 1 d . . . . .
H2 H 0.5715 0.1211 0.7163 0.053 Uiso 1 1 calc R U . . .
C5 C 0.5851(3) 0.0344(3) 0.75780(13) 0.0506(14) Uani 1 1 d . . . . .
H3 H 0.5683 -0.0095 0.7422 0.061 Uiso 1 1 calc R U . . .
C6 C 0.6085(3) 0.0208(3) 0.79599(13) 0.0492(13) Uani 1 1 d . . . . .
H4 H 0.6086 -0.0322 0.8060 0.059 Uiso 1 1 calc R U . . .
C7 C 0.6318(3) 0.0863(3) 0.81939(12) 0.0410(12) Uani 1 1 d . . . . .
H5 H 0.6482 0.0770 0.8451 0.049 Uiso 1 1 calc R U . . .
C8 C 0.6309(3) 0.1651(2) 0.80503(11) 0.0323(11) Uani 1 1 d . . . . .
C9 C 0.6523(3) 0.2351(2) 0.83159(11) 0.0325(11) Uani 1 1 d . . . . .
C10 C 0.6479(3) 0.3167(2) 0.81443(10) 0.0288(11) Uani 1 1 d . . . . .
C11 C 0.6587(3) 0.3947(3) 0.83146(11) 0.0307(11) Uani 1 1 d . . . . .
C12 C 0.6409(3) 0.4522(3) 0.80289(11) 0.0310(11) Uani 1 1 d . . . . .
C13 C 0.6312(3) 0.5415(3) 0.80573(12) 0.0341(11) Uani 1 1 d . . . . .
C14 C 0.6601(3) 0.5937(3) 0.77668(12) 0.0390(12) Uani 1 1 d . . . . .
H6 H 0.6875 0.5724 0.7547 0.047 Uiso 1 1 calc R U . . .
C15 C 0.6484(3) 0.6783(3) 0.78020(14) 0.0450(13) Uani 1 1 d . . . . .
C16 C 0.6600(3) 0.8099(3) 0.74972(16) 0.0853(19) Uani 1 1 d . . . . .
H8 H 0.5972 0.8170 0.7497 0.128 Uiso 1 1 calc R U . . .
H7 H 0.6845 0.8352 0.7269 0.128 Uiso 1 1 calc R U . . .
H9 H 0.6845 0.8349 0.7726 0.128 Uiso 1 1 calc R U . . .
C17 C 0.6083(3) 0.7104(3) 0.81264(15) 0.0517(13) Uani 1 1 d . . . . .
H10 H 0.6012 0.7668 0.8152 0.062 Uiso 1 1 calc R U . . .
C18 C 0.5789(3) 0.6579(3) 0.84127(14) 0.0547(14) Uani 1 1 d . . . . .
H11 H 0.5511 0.6794 0.8631 0.066 Uiso 1 1 calc R U . . .
C19 C 0.5897(3) 0.5751(3) 0.83826(12) 0.0442(13) Uani 1 1 d . . . . .
H12 H 0.5694 0.5409 0.8580 0.053 Uiso 1 1 calc R U . . .
C20 C 0.6837(3) 0.4093(2) 0.87320(10) 0.0310(11) Uani 1 1 d . . . . .
H13 H 0.6896 0.4688 0.8758 0.037 Uiso 1 1 calc R U . . .
C21 C 0.7733(3) 0.3747(2) 0.88263(12) 0.0353(12) Uani 1 1 d . . . . .
C22 C 0.8717(3) 0.3106(3) 0.93063(13) 0.0784(18) Uani 1 1 d . . . . .
H16 H 0.8833 0.3278 0.9569 0.118 Uiso 1 1 calc R U . . .
H14 H 0.9148 0.3340 0.9135 0.118 Uiso 1 1 calc R U . . .
H15 H 0.8746 0.2519 0.9292 0.118 Uiso 1 1 calc R U . . .
C23 C 0.7143(4) 0.3190(3) 0.94359(13) 0.0460(13) Uani 1 1 d . . . . .
C24 C 0.5590(3) 0.3224(3) 0.95969(12) 0.0664(16) Uani 1 1 d . . . . .
H19 H 0.5092 0.3574 0.9553 0.100 Uiso 1 1 calc R U . . .
H18 H 0.5777 0.3272 0.9863 0.100 Uiso 1 1 calc R U . . .
H17 H 0.5428 0.2666 0.9544 0.100 Uiso 1 1 calc R U . . .
C25 C 0.6098(3) 0.3855(3) 0.89965(12) 0.0356(12) Uani 1 1 d . . . . .
C26 C 0.6276(3) 0.4358(3) 0.63230(11) 0.0311(11) Uani 1 1 d . . . . .
C27 C 0.6139(3) 0.5013(3) 0.65996(12) 0.0351(11) Uani 1 1 d . . . . .
C28 C 0.6140(3) 0.5852(2) 0.64258(11) 0.0328(11) Uani 1 1 d . . . . .
C29 C 0.5925(3) 0.6507(3) 0.66605(13) 0.0469(13) Uani 1 1 d . . . . .
H21 H 0.5794 0.6425 0.6922 0.056 Uiso 1 1 calc R U . . .
C30 C 0.5907(3) 0.7287(3) 0.65042(13) 0.0537(14) Uani 1 1 d . . . . .
H22 H 0.5740 0.7725 0.6661 0.064 Uiso 1 1 calc R U . . .
C31 C 0.6130(3) 0.7429(3) 0.61222(14) 0.0520(13) Uani 1 1 d . . . . .
H23 H 0.6131 0.7960 0.6023 0.062 Uiso 1 1 calc R U . . .
C32 C 0.6351(3) 0.6775(3) 0.58896(12) 0.0415(12) Uani 1 1 d . . . . .
H24 H 0.6501 0.6866 0.5631 0.050 Uiso 1 1 calc R U . . .
C33 C 0.6356(3) 0.5982(3) 0.60336(11) 0.0329(11) Uani 1 1 d . . . . .
C34 C 0.6563(3) 0.5282(3) 0.57681(12) 0.0341(11) Uani 1 1 d . . . . .
C35 C 0.6490(3) 0.4464(3) 0.59351(11) 0.0303(11) Uani 1 1 d . . . . .
C36 C 0.6578(3) 0.3684(2) 0.57660(11) 0.0308(11) Uani 1 1 d . . . . .
C37 C 0.6400(2) 0.3117(2) 0.60534(11) 0.0287(10) Uani 1 1 d . . . . .
C38 C 0.6323(3) 0.2215(3) 0.60375(11) 0.0314(11) Uani 1 1 d . . . . .
C39 C 0.6614(3) 0.1715(3) 0.63351(11) 0.0344(12) Uani 1 1 d . . . . .
H25 H 0.6879 0.1944 0.6554 0.041 Uiso 1 1 calc R U . . .
C40 C 0.6512(3) 0.0875(3) 0.63084(12) 0.0348(11) Uani 1 1 d . . . . .
C41 C 0.6604(3) -0.0433(3) 0.66331(15) 0.0755(17) Uani 1 1 d . . . . .
H26 H 0.5976 -0.0500 0.6628 0.113 Uiso 1 1 calc R U . . .
H27 H 0.6835 -0.0671 0.6867 0.113 Uiso 1 1 calc R U . . .
H28 H 0.6859 -0.0702 0.6411 0.113 Uiso 1 1 calc R U . . .
C42 C 0.6138(3) 0.0516(3) 0.59835(14) 0.0467(13) Uani 1 1 d . . . . .
H29 H 0.6083 -0.0050 0.5964 0.056 Uiso 1 1 calc R U . . .
C43 C 0.5848(3) 0.1020(3) 0.56898(13) 0.0522(14) Uani 1 1 d . . . . .
H30 H 0.5588 0.0788 0.5471 0.063 Uiso 1 1 calc R U . . .
C44 C 0.5930(3) 0.1856(3) 0.57101(11) 0.0417(12) Uani 1 1 d . . . . .
H31 H 0.5727 0.2183 0.5507 0.050 Uiso 1 1 calc R U . . .
C45 C 0.6834(3) 0.3531(2) 0.53471(10) 0.0312(11) Uani 1 1 d . . . . .
H32 H 0.6882 0.2934 0.5322 0.037 Uiso 1 1 calc R U . . .
C46 C 0.7738(3) 0.3860(2) 0.52514(13) 0.0352(11) Uani 1 1 d . . . . .
C47 C 0.8745(3) 0.4365(3) 0.47587(14) 0.0759(17) Uani 1 1 d . . . . .
H34 H 0.8897 0.4897 0.4857 0.114 Uiso 1 1 calc R U . . .
H35 H 0.8776 0.4369 0.4480 0.114 Uiso 1 1 calc R U . . .
H33 H 0.9149 0.3965 0.4859 0.114 Uiso 1 1 calc R U . . .
C48 C 0.7187(4) 0.4317(3) 0.46182(13) 0.0449(13) Uani 1 1 d . . . . .
C49 C 0.5637(3) 0.4322(3) 0.44440(13) 0.0755(18) Uani 1 1 d . . . . .
H38 H 0.5088 0.4102 0.4535 0.113 Uiso 1 1 calc R U . . .
H37 H 0.5776 0.4090 0.4194 0.113 Uiso 1 1 calc R U . . .
H36 H 0.5590 0.4907 0.4421 0.113 Uiso 1 1 calc R U . . .
C50 C 0.6107(3) 0.3779(3) 0.50713(12) 0.0401(12) Uani 1 1 d . . . . .
N1 N 0.6229(2) 0.4102(2) 0.76908(9) 0.0332(9) Uani 1 1 d . . . . .
H1 H 0.6114 0.4326 0.7470 0.040 Uiso 1 1 calc R U . . .
N2 N 0.6311(3) 0.3466(2) 0.93386(9) 0.0405(10) Uani 1 1 d . . . . .
N3 N 0.7829(2) 0.3383(2) 0.91889(10) 0.0419(10) Uani 1 1 d . . . . .
N4 N 0.6236(2) 0.3537(2) 0.63922(9) 0.0343(9) Uani 1 1 d . . . . .
H20 H 0.6124 0.3316 0.6614 0.041 Uiso 1 1 calc R U . . .
N5 N 0.7855(2) 0.4157(2) 0.48800(10) 0.0384(9) Uani 1 1 d . . . . .
N6 N 0.6339(2) 0.4118(2) 0.47227(9) 0.0405(10) Uani 1 1 d . . . . .
O1 O 0.5942(2) 0.27520(17) 0.71370(7) 0.0491(9) Uani 1 1 d . . . . .
O2 O 0.6696(2) 0.22445(17) 0.86599(8) 0.0509(9) Uani 1 1 d . . . . .
O3 O 0.6805(2) 0.72372(19) 0.74960(9) 0.0671(10) Uani 1 1 d . . . . .
O4 O 0.8347(2) 0.38099(19) 0.86068(9) 0.0568(10) Uani 1 1 d . . . . .
O5 O 0.7261(2) 0.2794(2) 0.97285(9) 0.0780(12) Uani 1 1 d . . . . .
O6 O 0.5341(2) 0.4013(2) 0.89195(8) 0.0586(10) Uani 1 1 d . . . . .
O7 O 0.6022(2) 0.48874(16) 0.69497(8) 0.0495(9) Uani 1 1 d . . . . .
O8 O 0.67660(19) 0.53877(17) 0.54250(8) 0.0486(9) Uani 1 1 d . . . . .
O9 O 0.6817(2) 0.04307(18) 0.66221(9) 0.0562(9) Uani 1 1 d . . . . .
O10 O 0.8337(2) 0.38295(19) 0.54811(9) 0.0569(10) Uani 1 1 d . . . . .
O11 O 0.7341(2) 0.4630(2) 0.43074(9) 0.0764(12) Uani 1 1 d . . . . .
O12 O 0.5343(2) 0.3650(2) 0.51535(8) 0.0686(11) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.359(5) . ?
C1 C10 1.381(5) . ?
C1 C2 1.445(5) . ?
C2 O1 1.230(4) . ?
C2 C3 1.493(5) . ?
C3 C4 1.397(5) . ?
C3 C8 1.401(5) . ?
C4 C5 1.382(5) . ?
C4 H2 0.9300 . ?
C5 C6 1.377(5) . ?
C5 H3 0.9300 . ?
C6 C7 1.383(5) . ?
C6 H4 0.9300 . ?
C7 C8 1.377(5) . ?
C7 H5 0.9300 . ?
C8 C9 1.497(5) . ?
C9 O2 1.223(4) . ?
C9 C10 1.457(5) . ?
C10 C11 1.409(5) . ?
C11 C12 1.384(5) . ?
C11 C20 1.502(5) . ?
C12 N1 1.375(4) . ?
C12 C13 1.467(5) . ?
C13 C14 1.384(5) . ?
C13 C19 1.394(5) . ?
C14 C15 1.395(6) . ?
C14 H6 0.9300 . ?
C15 C17 1.374(6) . ?
C15 O3 1.375(5) . ?
C16 O3 1.440(5) . ?
C16 H8 0.9600 . ?
C16 H7 0.9600 . ?
C16 H9 0.9600 . ?
C17 C18 1.378(6) . ?
C17 H10 0.9300 . ?
C18 C19 1.366(6) . ?
C18 H11 0.9300 . ?
C19 H12 0.9300 . ?
C20 C25 1.496(5) . ?
C20 C21 1.507(5) . ?
C20 H13 0.9800 . ?
C21 O4 1.203(4) . ?
C21 N3 1.387(5) . ?
C22 N3 1.479(5) . ?
C22 H16 0.9600 . ?
C22 H14 0.9600 . ?
C22 H15 0.9600 . ?
C23 O5 1.208(5) . ?
C23 N3 1.380(5) . ?
C23 N2 1.382(5) . ?
C24 N2 1.463(5) . ?
C24 H19 0.9600 . ?
C24 H18 0.9600 . ?
C24 H17 0.9600 . ?
C25 O6 1.208(5) . ?
C25 N2 1.374(5) . ?
C26 N4 1.360(5) . ?
C26 C35 1.382(5) . ?
C26 C27 1.444(5) . ?
C27 O7 1.233(4) . ?
C27 C28 1.494(5) . ?
C28 C29 1.377(5) . ?
C28 C33 1.402(5) . ?
C29 C30 1.380(6) . ?
C29 H21 0.9300 . ?
C30 C31 1.375(5) . ?
C30 H22 0.9300 . ?
C31 C32 1.375(5) . ?
C31 H23 0.9300 . ?
C32 C33 1.383(5) . ?
C32 H24 0.9300 . ?
C33 C34 1.495(5) . ?
C34 O8 1.230(4) . ?
C34 C35 1.456(5) . ?
C35 C36 1.406(5) . ?
C36 C37 1.379(5) . ?
C36 C45 1.511(5) . ?
C37 N4 1.374(4) . ?
C37 C38 1.477(5) . ?
C38 C39 1.380(5) . ?
C38 C44 1.401(5) . ?
C39 C40 1.382(5) . ?
C39 H25 0.9300 . ?
C40 O9 1.378(5) . ?
C40 C42 1.383(5) . ?
C41 O9 1.446(5) . ?
C41 H26 0.9600 . ?
C41 H27 0.9600 . ?
C41 H28 0.9600 . ?
C42 C43 1.374(6) . ?
C42 H29 0.9300 . ?
C43 C44 1.370(6) . ?
C43 H30 0.9300 . ?
C44 H31 0.9300 . ?
C45 C50 1.509(5) . ?
C45 C46 1.512(5) . ?
C45 H32 0.9800 . ?
C46 O10 1.204(5) . ?
C46 N5 1.376(5) . ?
C47 N5 1.454(5) . ?
C47 H34 0.9600 . ?
C47 H35 0.9600 . ?
C47 H33 0.9600 . ?
C48 O11 1.206(5) . ?
C48 N6 1.376(5) . ?
C48 N5 1.380(5) . ?
C49 N6 1.470(5) . ?
C49 H38 0.9600 . ?
C49 H37 0.9600 . ?
C49 H36 0.9600 . ?
C50 O12 1.213(5) . ?
C50 N6 1.365(5) . ?
N1 H1 0.8600 . ?
N4 H20 0.8600 . ?

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
N1 C1 C10 107.7(3) . . ?
N1 C1 C2 127.6(4) . . ?
C10 C1 C2 124.6(4) . . ?
O1 C2 C1 122.8(4) . . ?
O1 C2 C3 122.8(4) . . ?
C1 C2 C3 114.4(3) . . ?
C4 C3 C8 119.3(4) . . ?
C4 C3 C2 118.3(4) . . ?
C8 C3 C2 122.4(4) . . ?
C5 C4 C3 119.7(4) . . ?
C5 C4 H2 120.2 . . ?
C3 C4 H2 120.2 . . ?
C6 C5 C4 120.8(4) . . ?
C6 C5 H3 119.6 . . ?
C4 C5 H3 119.6 . . ?
C5 C6 C7 119.6(4) . . ?
C5 C6 H4 120.2 . . ?
C7 C6 H4 120.2 . . ?
C8 C7 C6 120.7(4) . . ?
C8 C7 H5 119.6 . . ?
C6 C7 H5 119.6 . . ?
C7 C8 C3 119.8(4) . . ?
C7 C8 C9 119.5(4) . . ?
C3 C8 C9 120.7(4) . . ?
O2 C9 C10 122.0(4) . . ?
O2 C9 C8 121.8(4) . . ?
C10 C9 C8 116.1(3) . . ?
C1 C10 C11 107.7(4) . . ?
C1 C10 C9 121.6(4) . . ?
C11 C10 C9 130.6(3) . . ?
C12 C11 C10 107.2(3) . . ?
C12 C11 C20 128.2(4) . . ?
C10 C11 C20 124.6(4) . . ?
N1 C12 C11 107.4(3) . . ?
N1 C12 C13 122.0(4) . . ?
C11 C12 C13 130.2(4) . . ?
C14 C13 C19 118.7(4) . . ?
C14 C13 C12 122.1(4) . . ?
C19 C13 C12 119.2(4) . . ?
C13 C14 C15 120.4(4) . . ?
C13 C14 H6 119.8 . . ?
C15 C14 H6 119.8 . . ?
C17 C15 O3 124.8(4) . . ?
C17 C15 C14 120.3(4) . . ?
O3 C15 C14 114.9(4) . . ?
O3 C16 H8 109.5 . . ?
O3 C16 H7 109.5 . . ?
H8 C16 H7 109.5 . . ?
O3 C16 H9 109.5 . . ?
H8 C16 H9 109.5 . . ?
H7 C16 H9 109.5 . . ?
C15 C17 C18 119.0(4) . . ?
C15 C17 H10 120.5 . . ?
C18 C17 H10 120.5 . . ?
C19 C18 C17 121.5(4) . . ?
C19 C18 H11 119.3 . . ?
C17 C18 H11 119.3 . . ?
C18 C19 C13 120.2(4) . . ?
C18 C19 H12 119.9 . . ?
C13 C19 H12 119.9 . . ?
C25 C20 C11 110.4(3) . . ?
C25 C20 C21 116.8(4) . . ?
C11 C20 C21 112.0(3) . . ?
C25 C20 H13 105.6 . . ?
C11 C20 H13 105.6 . . ?
C21 C20 H13 105.6 . . ?
O4 C21 N3 121.2(4) . . ?
O4 C21 C20 122.2(4) . . ?
N3 C21 C20 116.6(4) . . ?
N3 C22 H16 109.5 . . ?
N3 C22 H14 109.5 . . ?
H16 C22 H14 109.5 . . ?
N3 C22 H15 109.5 . . ?
H16 C22 H15 109.5 . . ?
H14 C22 H15 109.5 . . ?
O5 C23 N3 121.4(5) . . ?
O5 C23 N2 120.7(5) . . ?
N3 C23 N2 117.8(4) . . ?
N2 C24 H19 109.5 . . ?
N2 C24 H18 109.5 . . ?
H19 C24 H18 109.5 . . ?
N2 C24 H17 109.5 . . ?
H19 C24 H17 109.5 . . ?
H18 C24 H17 109.5 . . ?
O6 C25 N2 120.7(4) . . ?
O6 C25 C20 121.8(4) . . ?
N2 C25 C20 117.5(4) . . ?
N4 C26 C35 107.6(3) . . ?
N4 C26 C27 127.3(4) . . ?
C35 C26 C27 125.1(4) . . ?
O7 C27 C26 122.7(4) . . ?
O7 C27 C28 122.8(4) . . ?
C26 C27 C28 114.5(4) . . ?
C29 C28 C33 120.0(4) . . ?
C29 C28 C27 118.5(4) . . ?
C33 C28 C27 121.5(4) . . ?
C28 C29 C30 119.5(4) . . ?
C28 C29 H21 120.3 . . ?
C30 C29 H21 120.3 . . ?
C31 C30 C29 121.5(4) . . ?
C31 C30 H22 119.3 . . ?
C29 C30 H22 119.3 . . ?
C30 C31 C32 118.9(4) . . ?
C30 C31 H23 120.6 . . ?
C32 C31 H23 120.6 . . ?
C31 C32 C33 121.2(4) . . ?
C31 C32 H24 119.4 . . ?
C33 C32 H24 119.4 . . ?
C32 C33 C28 118.9(4) . . ?
C32 C33 C34 119.8(4) . . ?
C28 C33 C34 121.3(4) . . ?
O8 C34 C35 121.6(4) . . ?
O8 C34 C33 122.0(4) . . ?
C35 C34 C33 116.3(4) . . ?
C26 C35 C36 107.8(4) . . ?
C26 C35 C34 120.8(4) . . ?
C36 C35 C34 131.3(4) . . ?
C37 C36 C35 107.0(3) . . ?
C37 C36 C45 128.4(4) . . ?
C35 C36 C45 124.6(4) . . ?
N4 C37 C36 107.9(3) . . ?
N4 C37 C38 121.0(3) . . ?
C36 C37 C38 131.1(4) . . ?
C39 C38 C44 118.9(4) . . ?
C39 C38 C37 122.4(4) . . ?
C44 C38 C37 118.7(4) . . ?
C38 C39 C40 120.1(4) . . ?
C38 C39 H25 120.0 . . ?
C40 C39 H25 120.0 . . ?
O9 C40 C39 115.6(4) . . ?
O9 C40 C42 123.2(4) . . ?
C39 C40 C42 121.3(4) . . ?
O9 C41 H26 109.5 . . ?
O9 C41 H27 109.5 . . ?
H26 C41 H27 109.5 . . ?
O9 C41 H28 109.5 . . ?
H26 C41 H28 109.5 . . ?
H27 C41 H28 109.5 . . ?
C43 C42 C40 118.1(4) . . ?
C43 C42 H29 120.9 . . ?
C40 C42 H29 120.9 . . ?
C44 C43 C42 121.9(4) . . ?
C44 C43 H30 119.0 . . ?
C42 C43 H30 119.0 . . ?
C43 C44 C38 119.7(4) . . ?
C43 C44 H31 120.1 . . ?
C38 C44 H31 120.1 . . ?
C50 C45 C36 111.4(3) . . ?
C50 C45 C46 115.6(4) . . ?
C36 C45 C46 112.5(3) . . ?
C50 C45 H32 105.4 . . ?
C36 C45 H32 105.4 . . ?
C46 C45 H32 105.4 . . ?
O10 C46 N5 121.6(4) . . ?
O10 C46 C45 121.9(4) . . ?
N5 C46 C45 116.4(4) . . ?
N5 C47 H34 109.5 . . ?
N5 C47 H35 109.5 . . ?
H34 C47 H35 109.5 . . ?
N5 C47 H33 109.5 . . ?
H34 C47 H33 109.5 . . ?
H35 C47 H33 109.5 . . ?
O11 C48 N6 120.7(4) . . ?
O11 C48 N5 121.0(5) . . ?
N6 C48 N5 118.3(4) . . ?
N6 C49 H38 109.5 . . ?
N6 C49 H37 109.5 . . ?
H38 C49 H37 109.5 . . ?
N6 C49 H36 109.5 . . ?
H38 C49 H36 109.5 . . ?
H37 C49 H36 109.5 . . ?
O12 C50 N6 121.4(4) . . ?
O12 C50 C45 120.5(4) . . ?
N6 C50 C45 118.1(4) . . ?
C1 N1 C12 109.9(3) . . ?
C1 N1 H1 125.0 . . ?
C12 N1 H1 125.0 . . ?
C25 N2 C23 124.9(4) . . ?
C25 N2 C24 117.9(4) . . ?
C23 N2 C24 116.7(4) . . ?
C23 N3 C21 124.8(4) . . ?
C23 N3 C22 116.8(4) . . ?
C21 N3 C22 118.1(4) . . ?
C26 N4 C37 109.6(3) . . ?
C26 N4 H20 125.2 . . ?
C37 N4 H20 125.2 . . ?
C46 N5 C48 125.1(4) . . ?
C46 N5 C47 117.8(4) . . ?
C48 N5 C47 116.9(4) . . ?
C50 N6 C48 124.4(4) . . ?
C50 N6 C49 118.4(4) . . ?
C48 N6 C49 117.1(4) . . ?
C15 O3 C16 116.6(4) . . ?
C40 O9 C41 117.2(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
N1 C1 C2 O1 4.7(7) . . . . ?
C10 C1 C2 O1 -176.2(4) . . . . ?
N1 C1 C2 C3 -174.2(4) . . . . ?
C10 C1 C2 C3 4.8(6) . . . . ?
O1 C2 C3 C4 -4.3(6) . . . . ?
C1 C2 C3 C4 174.7(4) . . . . ?
O1 C2 C3 C8 176.5(4) . . . . ?
C1 C2 C3 C8 -4.5(6) . . . . ?
C8 C3 C4 C5 -0.2(7) . . . . ?
C2 C3 C4 C5 -179.4(4) . . . . ?
C3 C4 C5 C6 -1.4(7) . . . . ?
C4 C5 C6 C7 1.2(7) . . . . ?
C5 C6 C7 C8 0.7(7) . . . . ?
C6 C7 C8 C3 -2.3(6) . . . . ?
C6 C7 C8 C9 177.1(4) . . . . ?
C4 C3 C8 C7 2.1(6) . . . . ?
C2 C3 C8 C7 -178.8(4) . . . . ?
C4 C3 C8 C9 -177.3(4) . . . . ?
C2 C3 C8 C9 1.8(6) . . . . ?
C7 C8 C9 O2 -0.8(6) . . . . ?
C3 C8 C9 O2 178.5(4) . . . . ?
C7 C8 C9 C10 -178.5(4) . . . . ?
C3 C8 C9 C10 0.8(6) . . . . ?
N1 C1 C10 C11 -0.4(5) . . . . ?
C2 C1 C10 C11 -179.6(4) . . . . ?
N1 C1 C10 C9 176.8(3) . . . . ?
C2 C1 C10 C9 -2.4(6) . . . . ?
O2 C9 C10 C1 -178.3(4) . . . . ?
C8 C9 C10 C1 -0.7(6) . . . . ?
O2 C9 C10 C11 -1.9(7) . . . . ?
C8 C9 C10 C11 175.8(4) . . . . ?
C1 C10 C11 C12 1.5(5) . . . . ?
C9 C10 C11 C12 -175.3(4) . . . . ?
C1 C10 C11 C20 -179.2(4) . . . . ?
C9 C10 C11 C20 3.9(7) . . . . ?
C10 C11 C12 N1 -2.1(5) . . . . ?
C20 C11 C12 N1 178.7(4) . . . . ?
C10 C11 C12 C13 171.2(4) . . . . ?
C20 C11 C12 C13 -8.0(7) . . . . ?
N1 C12 C13 C14 -43.5(6) . . . . ?
C11 C12 C13 C14 144.0(5) . . . . ?
N1 C12 C13 C19 135.0(4) . . . . ?
C11 C12 C13 C19 -37.4(6) . . . . ?
C19 C13 C14 C15 0.5(6) . . . . ?
C12 C13 C14 C15 179.0(4) . . . . ?
C13 C14 C15 C17 0.3(7) . . . . ?
C13 C14 C15 O3 179.5(4) . . . . ?
O3 C15 C17 C18 179.9(4) . . . . ?
C14 C15 C17 C18 -0.9(7) . . . . ?
C15 C17 C18 C19 0.8(7) . . . . ?
C17 C18 C19 C13 -0.1(7) . . . . ?
C14 C13 C19 C18 -0.6(6) . . . . ?
C12 C13 C19 C18 -179.1(4) . . . . ?
C12 C11 C20 C25 109.4(5) . . . . ?
C10 C11 C20 C25 -69.7(5) . . . . ?
C12 C11 C20 C21 -118.7(5) . . . . ?
C10 C11 C20 C21 62.2(5) . . . . ?
C25 C20 C21 O4 170.1(4) . . . . ?
C11 C20 C21 O4 41.5(6) . . . . ?
C25 C20 C21 N3 -12.7(5) . . . . ?
C11 C20 C21 N3 -141.4(4) . . . . ?
C11 C20 C25 O6 -41.2(6) . . . . ?
C21 C20 C25 O6 -170.6(4) . . . . ?
C11 C20 C25 N2 140.5(4) . . . . ?
C21 C20 C25 N2 11.1(5) . . . . ?
N4 C26 C27 O7 5.0(7) . . . . ?
C35 C26 C27 O7 -173.7(4) . . . . ?
N4 C26 C27 C28 -174.2(4) . . . . ?
C35 C26 C27 C28 7.1(6) . . . . ?
O7 C27 C28 C29 -5.8(6) . . . . ?
C26 C27 C28 C29 173.4(4) . . . . ?
O7 C27 C28 C33 174.0(4) . . . . ?
C26 C27 C28 C33 -6.8(6) . . . . ?
C33 C28 C29 C30 1.3(7) . . . . ?
C27 C28 C29 C30 -178.8(4) . . . . ?
C28 C29 C30 C31 -2.4(7) . . . . ?
C29 C30 C31 C32 1.9(7) . . . . ?
C30 C31 C32 C33 -0.2(7) . . . . ?
C31 C32 C33 C28 -0.8(6) . . . . ?
C31 C32 C33 C34 177.4(4) . . . . ?
C29 C28 C33 C32 0.3(6) . . . . ?
C27 C28 C33 C32 -179.6(4) . . . . ?
C29 C28 C33 C34 -178.0(4) . . . . ?
C27 C28 C33 C34 2.2(6) . . . . ?
C32 C33 C34 O8 2.9(6) . . . . ?
C28 C33 C34 O8 -178.9(4) . . . . ?
C32 C33 C34 C35 -175.6(4) . . . . ?
C28 C33 C34 C35 2.6(6) . . . . ?
N4 C26 C35 C36 0.3(5) . . . . ?
C27 C26 C35 C36 179.2(4) . . . . ?
N4 C26 C35 C34 178.6(4) . . . . ?
C27 C26 C35 C34 -2.5(6) . . . . ?
O8 C34 C35 C26 178.9(4) . . . . ?
C33 C34 C35 C26 -2.6(6) . . . . ?
O8 C34 C35 C36 -3.2(7) . . . . ?
C33 C34 C35 C36 175.3(4) . . . . ?
C26 C35 C36 C37 1.0(5) . . . . ?
C34 C35 C36 C37 -177.1(4) . . . . ?
C26 C35 C36 C45 -178.2(4) . . . . ?
C34 C35 C36 C45 3.7(7) . . . . ?
C35 C36 C37 N4 -1.8(4) . . . . ?
C45 C36 C37 N4 177.3(4) . . . . ?
C35 C36 C37 C38 174.5(4) . . . . ?
C45 C36 C37 C38 -6.3(7) . . . . ?
N4 C37 C38 C39 -40.6(6) . . . . ?
C36 C37 C38 C39 143.5(4) . . . . ?
N4 C37 C38 C44 138.6(4) . . . . ?
C36 C37 C38 C44 -37.4(6) . . . . ?
C44 C38 C39 C40 -0.3(6) . . . . ?
C37 C38 C39 C40 178.9(4) . . . . ?
C38 C39 C40 O9 -179.4(4) . . . . ?
C38 C39 C40 C42 1.3(6) . . . . ?
O9 C40 C42 C43 179.3(4) . . . . ?
C39 C40 C42 C43 -1.5(6) . . . . ?
C40 C42 C43 C44 0.7(7) . . . . ?
C42 C43 C44 C38 0.2(7) . . . . ?
C39 C38 C44 C43 -0.4(6) . . . . ?
C37 C38 C44 C43 -179.7(4) . . . . ?
C37 C36 C45 C50 110.8(5) . . . . ?
C35 C36 C45 C50 -70.2(5) . . . . ?
C37 C36 C45 C46 -117.5(5) . . . . ?
C35 C36 C45 C46 61.5(5) . . . . ?
C50 C45 C46 O10 166.7(4) . . . . ?
C36 C45 C46 O10 37.1(6) . . . . ?
C50 C45 C46 N5 -16.6(5) . . . . ?
C36 C45 C46 N5 -146.2(3) . . . . ?
C36 C45 C50 O12 -38.9(6) . . . . ?
C46 C45 C50 O12 -168.9(4) . . . . ?
C36 C45 C50 N6 143.7(4) . . . . ?
C46 C45 C50 N6 13.6(5) . . . . ?
C10 C1 N1 C12 -0.9(5) . . . . ?
C2 C1 N1 C12 178.2(4) . . . . ?
C11 C12 N1 C1 1.9(5) . . . . ?
C13 C12 N1 C1 -172.1(4) . . . . ?
O6 C25 N2 C23 173.5(4) . . . . ?
C20 C25 N2 C23 -8.2(6) . . . . ?
O6 C25 N2 C24 2.3(6) . . . . ?
C20 C25 N2 C24 -179.3(4) . . . . ?
O5 C23 N2 C25 -173.8(4) . . . . ?
N3 C23 N2 C25 6.3(6) . . . . ?
O5 C23 N2 C24 -2.6(6) . . . . ?
N3 C23 N2 C24 177.5(4) . . . . ?
O5 C23 N3 C21 171.8(4) . . . . ?
N2 C23 N3 C21 -8.3(6) . . . . ?
O5 C23 N3 C22 -2.0(6) . . . . ?
N2 C23 N3 C22 177.9(4) . . . . ?
O4 C21 N3 C23 -171.0(4) . . . . ?
C20 C21 N3 C23 11.8(6) . . . . ?
O4 C21 N3 C22 2.6(6) . . . . ?
C20 C21 N3 C22 -174.5(4) . . . . ?
C35 C26 N4 C37 -1.4(5) . . . . ?
C27 C26 N4 C37 179.7(4) . . . . ?
C36 C37 N4 C26 2.1(4) . . . . ?
C38 C37 N4 C26 -174.7(4) . . . . ?
O10 C46 N5 C48 -170.7(4) . . . . ?
C45 C46 N5 C48 12.6(6) . . . . ?
O10 C46 N5 C47 5.7(6) . . . . ?
C45 C46 N5 C47 -171.0(4) . . . . ?
O11 C48 N5 C46 174.9(4) . . . . ?
N6 C48 N5 C46 -4.4(6) . . . . ?
O11 C48 N5 C47 -1.5(7) . . . . ?
N6 C48 N5 C47 179.2(4) . . . . ?
O12 C50 N6 C48 176.7(4) . . . . ?
C45 C50 N6 C48 -5.9(6) . . . . ?
O12 C50 N6 C49 -0.5(6) . . . . ?
C45 C50 N6 C49 176.8(4) . . . . ?
O11 C48 N6 C50 -178.6(4) . . . . ?
N5 C48 N6 C50 0.7(6) . . . . ?
O11 C48 N6 C49 -1.4(7) . . . . ?
N5 C48 N6 C49 177.9(4) . . . . ?
C17 C15 O3 C16 -8.4(6) . . . . ?
C14 C15 O3 C16 172.4(4) . . . . ?
C39 C40 O9 C41 170.8(4) . . . . ?
C42 C40 O9 C41 -10.0(6) . . . . ?

_refine_diff_density_max         0.259
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.063


# start Validation Reply Form
_vrf_RINTA01_OO_a                
;
PROBLEM: The value of Rint is greater than 0.25
RESPONSE: Due to weak diffraction at high anlges as it was small crystal.
;
_vrf_PLAT020_OO_a                
;
PROBLEM: The Value of Rint is Greater Than 0.12 .........      0.357 Report
RESPONSE:Due to weak diffraction at high anlges as it was small crystal.
;

# end Validation Reply Form
####################################################################### 
# 
# 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_M_a
_database_code_depnum_ccdc_archive 'CCDC 1973971'
loop_
_audit_author_name
_audit_author_address
'ANOOP KUMAR PANDAY'
;Indian Institute of Technology Patna, Patna
India
;
_audit_update_record             
;
2019-12-24 deposited with the CCDC.	2020-06-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H16 F3 N3 O5'
_chemical_formula_weight         495.41

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'

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

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

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

_cell_length_a                   12.391(7)
_cell_length_b                   8.165(5)
_cell_length_c                   21.573(12)
_cell_angle_alpha                90
_cell_angle_beta                 94.106(14)
_cell_angle_gamma                90
_cell_volume                     2177(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1957
_cell_measurement_theta_min      2.990
_cell_measurement_theta_max      22.493

_exptl_crystal_description       NEEDLELIKE
_exptl_crystal_colour            YELLOW
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.512
_exptl_crystal_F_000             1016
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.124
_shelx_estimated_absorpt_T_min   0.941
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.985
_exptl_absorpt_correction_T_max  0.994
_exptl_absorpt_process_details   SADABS-2016/2
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15757
_diffrn_reflns_av_unetI/netI     0.2070
_diffrn_reflns_av_R_equivalents  0.2325
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.990
_diffrn_reflns_theta_max         22.493
_diffrn_reflns_theta_full        22.493
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2832
_reflns_number_gt                1122
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0327P)²+12.1832P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2832
_refine_ls_number_parameters     327
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2596
_refine_ls_R_factor_gt           0.0973
_refine_ls_wR_factor_ref         0.2240
_refine_ls_wR_factor_gt          0.1587
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_restrained_S_all      1.017
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.5681(8) 0.4326(13) 0.8215(5) 0.043(3) Uani 1 1 d . . . . .
C2 C 0.5577(8) 0.4039(13) 0.8868(5) 0.045(3) Uani 1 1 d . . . . .
C3 C 0.6579(8) 0.4405(12) 0.9268(5) 0.039(3) Uani 1 1 d . . . . .
C4 C 0.6552(10) 0.4299(13) 0.9908(5) 0.058(3) Uani 1 1 d . . . . .
H2 H 0.5912 0.4013 1.0081 0.070 Uiso 1 1 calc R U . . .
C5 C 0.7469(12) 0.4617(14) 1.0289(6) 0.068(4) Uani 1 1 d . . . . .
H3 H 0.7453 0.4511 1.0718 0.082 Uiso 1 1 calc R U . . .
C6 C 0.8390(10) 0.5080(15) 1.0041(6) 0.070(4) Uani 1 1 d . . . . .
H4 H 0.8996 0.5342 1.0301 0.084 Uiso 1 1 calc R U . . .
C7 C 0.8446(9) 0.5169(14) 0.9406(6) 0.061(3) Uani 1 1 d . . . . .
H5 H 0.9097 0.5436 0.9242 0.073 Uiso 1 1 calc R U . . .
C8 C 0.7542(9) 0.4865(12) 0.9015(5) 0.042(3) Uani 1 1 d . . . . .
C9 C 0.7607(7) 0.5083(12) 0.8336(5) 0.039(3) Uani 1 1 d . . . . .
C10 C 0.6610(7) 0.4818(11) 0.7959(5) 0.032(3) Uani 1 1 d . . . . .
C11 C 0.6391(7) 0.4904(11) 0.7307(5) 0.033(3) Uani 1 1 d . . . . .
C12 C 0.5301(8) 0.4541(12) 0.7196(5) 0.040(3) Uani 1 1 d . . . . .
C13 C 0.4573(8) 0.4492(13) 0.6629(5) 0.042(3) Uani 1 1 d . . . . .
C14 C 0.4881(8) 0.3800(13) 0.6085(5) 0.050(3) Uani 1 1 d . . . . .
H6 H 0.5561 0.3322 0.6071 0.060 Uiso 1 1 calc R U . . .
C15 C 0.4164(9) 0.3826(13) 0.5555(5) 0.056(3) Uani 1 1 d . . . . .
H7 H 0.4371 0.3370 0.5187 0.067 Uiso 1 1 calc R U . . .
C16 C 0.3140(8) 0.4526(14) 0.5572(6) 0.047(3) Uani 1 1 d . . . . .
C17 C 0.2415(12) 0.458(2) 0.5020(7) 0.078(4) Uani 1 1 d . . . . .
C18 C 0.2849(8) 0.5182(14) 0.6118(6) 0.054(3) Uani 1 1 d . . . . .
H8 H 0.2162 0.5631 0.6136 0.065 Uiso 1 1 calc R U . . .
C19 C 0.3551(9) 0.5195(13) 0.6644(5) 0.051(3) Uani 1 1 d . . . . .
H9 H 0.3342 0.5672 0.7008 0.061 Uiso 1 1 calc R U . . .
C20 C 0.7159(7) 0.5399(11) 0.6837(4) 0.034(3) Uani 1 1 d . . . . .
H10 H 0.6715 0.5546 0.6447 0.041 Uiso 1 1 calc R U . . .
C21 C 0.7674(8) 0.7033(12) 0.6979(4) 0.033(3) Uani 1 1 d . . . . .
C22 C 0.9177(8) 0.8868(11) 0.6892(5) 0.059(3) Uani 1 1 d . . . . .
H16 H 0.9246 0.9141 0.7326 0.089 Uiso 1 1 calc R U . . .
H15 H 0.8719 0.9655 0.6673 0.089 Uiso 1 1 calc R U . . .
H14 H 0.9879 0.8880 0.6730 0.089 Uiso 1 1 calc R U . . .
C23 C 0.9359(9) 0.6021(13) 0.6603(5) 0.044(3) Uani 1 1 d . . . . .
C24 C 0.9661(8) 0.3155(13) 0.6376(6) 0.077(4) Uani 1 1 d . . . . .
H13 H 1.0315 0.3631 0.6244 0.116 Uiso 1 1 calc R U . . .
H11 H 0.9304 0.2557 0.6037 0.116 Uiso 1 1 calc R U . . .
H12 H 0.9833 0.2426 0.6718 0.116 Uiso 1 1 calc R U . . .
C25 C 0.7932(8) 0.4032(14) 0.6719(5) 0.045(3) Uani 1 1 d . . . . .
F1 F 0.2503(9) 0.5901(10) 0.4700(4) 0.172(5) Uani 1 1 d . . . . .
F2 F 0.2606(7) 0.3460(11) 0.4594(4) 0.113(3) Uani 1 1 d . . . . .
F3 F 0.1417(6) 0.4354(15) 0.5105(4) 0.170(5) Uani 1 1 d . . . . .
N1 N 0.4892(6) 0.4173(10) 0.7756(4) 0.046(2) Uani 1 1 d . . . . .
H1 H 0.4235 0.3890 0.7805 0.055 Uiso 1 1 calc R U . . .
N2 N 0.8706(6) 0.7249(9) 0.6813(4) 0.034(2) Uani 1 1 d . . . . .
N3 N 0.8942(6) 0.4462(10) 0.6573(4) 0.046(2) Uani 1 1 d . . . . .
O1 O 0.4747(6) 0.3523(10) 0.9067(3) 0.076(3) Uani 1 1 d . . . . .
O2 O 0.8450(5) 0.5453(8) 0.8106(3) 0.051(2) Uani 1 1 d . . . . .
O3 O 0.7190(5) 0.8150(8) 0.7202(3) 0.054(2) Uani 1 1 d . . . . .
O4 O 0.7656(6) 0.2608(9) 0.6731(4) 0.069(3) Uani 1 1 d . . . . .
O5 O 1.0273(6) 0.6299(9) 0.6484(4) 0.085(3) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 N1 1.346(11) . ?
C1 C10 1.372(11) . ?
C1 C2 1.443(13) . ?
C2 O1 1.218(10) . ?
C2 C3 1.491(13) . ?
C3 C4 1.385(12) . ?
C3 C8 1.400(12) . ?
C4 C5 1.380(14) . ?
C4 H2 0.9300 . ?
C5 C6 1.349(14) . ?
C5 H3 0.9300 . ?
C6 C7 1.378(13) . ?
C6 H4 0.9300 . ?
C7 C8 1.376(13) . ?
C7 H5 0.9300 . ?
C8 C9 1.482(13) . ?
C9 O2 1.226(10) . ?
C9 C10 1.446(12) . ?
C10 C11 1.415(12) . ?
C11 C12 1.387(12) . ?
C11 C20 1.495(11) . ?
C12 N1 1.376(10) . ?
C12 C13 1.466(13) . ?
C13 C14 1.382(12) . ?
C13 C19 1.393(12) . ?
C14 C15 1.396(13) . ?
C14 H6 0.9300 . ?
C15 C16 1.394(13) . ?
C15 H7 0.9300 . ?
C16 C18 1.366(13) . ?
C16 C17 1.440(15) . ?
C17 F3 1.276(15) . ?
C17 F1 1.293(16) . ?
C17 F2 1.329(13) . ?
C18 C19 1.379(12) . ?
C18 H8 0.9300 . ?
C19 H9 0.9300 . ?
C20 C21 1.500(12) . ?
C20 C25 1.505(12) . ?
C20 H10 0.9800 . ?
C21 O3 1.211(10) . ?
C21 N2 1.364(10) . ?
C22 N2 1.450(10) . ?
C22 H16 0.9600 . ?
C22 H15 0.9600 . ?
C22 H14 0.9600 . ?
C23 O5 1.200(10) . ?
C23 N3 1.374(12) . ?
C23 N2 1.386(11) . ?
C24 N3 1.472(10) . ?
C24 H13 0.9600 . ?
C24 H11 0.9600 . ?
C24 H12 0.9600 . ?
C25 O4 1.213(11) . ?
C25 N3 1.359(11) . ?
N1 H1 0.8600 . ?

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
N1 C1 C10 108.5(9) . . ?
N1 C1 C2 126.3(9) . . ?
C10 C1 C2 125.2(10) . . ?
O1 C2 C1 122.5(10) . . ?
O1 C2 C3 123.6(10) . . ?
C1 C2 C3 113.9(9) . . ?
C4 C3 C8 119.2(10) . . ?
C4 C3 C2 119.1(10) . . ?
C8 C3 C2 121.7(10) . . ?
C5 C4 C3 120.4(11) . . ?
C5 C4 H2 119.8 . . ?
C3 C4 H2 119.8 . . ?
C6 C5 C4 120.0(12) . . ?
C6 C5 H3 120.0 . . ?
C4 C5 H3 120.0 . . ?
C5 C6 C7 121.0(12) . . ?
C5 C6 H4 119.5 . . ?
C7 C6 H4 119.5 . . ?
C8 C7 C6 120.2(11) . . ?
C8 C7 H5 119.9 . . ?
C6 C7 H5 119.9 . . ?
C7 C8 C3 119.2(10) . . ?
C7 C8 C9 119.0(10) . . ?
C3 C8 C9 121.7(10) . . ?
O2 C9 C10 121.8(10) . . ?
O2 C9 C8 122.5(9) . . ?
C10 C9 C8 115.7(9) . . ?
C1 C10 C11 107.9(8) . . ?
C1 C10 C9 121.7(10) . . ?
C11 C10 C9 130.4(8) . . ?
C12 C11 C10 106.1(8) . . ?
C12 C11 C20 126.9(9) . . ?
C10 C11 C20 126.9(8) . . ?
N1 C12 C11 108.1(9) . . ?
N1 C12 C13 118.9(8) . . ?
C11 C12 C13 133.1(9) . . ?
C14 C13 C19 119.7(10) . . ?
C14 C13 C12 121.9(9) . . ?
C19 C13 C12 118.4(10) . . ?
C13 C14 C15 119.4(10) . . ?
C13 C14 H6 120.3 . . ?
C15 C14 H6 120.3 . . ?
C16 C15 C14 120.8(11) . . ?
C16 C15 H7 119.6 . . ?
C14 C15 H7 119.6 . . ?
C18 C16 C15 118.7(11) . . ?
C18 C16 C17 120.9(11) . . ?
C15 C16 C17 120.4(12) . . ?
F3 C17 F1 108.4(13) . . ?
F3 C17 F2 103.0(13) . . ?
F1 C17 F2 100.2(13) . . ?
F3 C17 C16 115.6(14) . . ?
F1 C17 C16 113.2(13) . . ?
F2 C17 C16 114.9(12) . . ?
C16 C18 C19 121.5(10) . . ?
C16 C18 H8 119.3 . . ?
C19 C18 H8 119.3 . . ?
C18 C19 C13 119.9(10) . . ?
C18 C19 H9 120.0 . . ?
C13 C19 H9 120.0 . . ?
C11 C20 C21 112.7(8) . . ?
C11 C20 C25 111.0(8) . . ?
C21 C20 C25 115.3(8) . . ?
C11 C20 H10 105.7 . . ?
C21 C20 H10 105.7 . . ?
C25 C20 H10 105.7 . . ?
O3 C21 N2 120.5(9) . . ?
O3 C21 C20 122.3(8) . . ?
N2 C21 C20 117.1(9) . . ?
N2 C22 H16 109.5 . . ?
N2 C22 H15 109.5 . . ?
H16 C22 H15 109.5 . . ?
N2 C22 H14 109.5 . . ?
H16 C22 H14 109.5 . . ?
H15 C22 H14 109.5 . . ?
O5 C23 N3 121.5(9) . . ?
O5 C23 N2 121.0(10) . . ?
N3 C23 N2 117.4(9) . . ?
N3 C24 H13 109.5 . . ?
N3 C24 H11 109.5 . . ?
H13 C24 H11 109.5 . . ?
N3 C24 H12 109.5 . . ?
H13 C24 H12 109.5 . . ?
H11 C24 H12 109.5 . . ?
O4 C25 N3 121.2(10) . . ?
O4 C25 C20 121.6(9) . . ?
N3 C25 C20 117.1(9) . . ?
C1 N1 C12 109.4(8) . . ?
C1 N1 H1 125.3 . . ?
C12 N1 H1 125.3 . . ?
C21 N2 C23 124.9(9) . . ?
C21 N2 C22 117.7(8) . . ?
C23 N2 C22 117.3(8) . . ?
C25 N3 C23 125.3(9) . . ?
C25 N3 C24 117.8(9) . . ?
C23 N3 C24 116.9(8) . . ?

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
N1 C1 C2 O1 4.4(18) . . . . ?
C10 C1 C2 O1 -176.2(11) . . . . ?
N1 C1 C2 C3 -176.6(10) . . . . ?
C10 C1 C2 C3 2.8(15) . . . . ?
O1 C2 C3 C4 -6.1(16) . . . . ?
C1 C2 C3 C4 175.0(9) . . . . ?
O1 C2 C3 C8 174.5(10) . . . . ?
C1 C2 C3 C8 -4.4(14) . . . . ?
C8 C3 C4 C5 -1.2(16) . . . . ?
C2 C3 C4 C5 179.4(10) . . . . ?
C3 C4 C5 C6 2.0(18) . . . . ?
C4 C5 C6 C7 -3.1(19) . . . . ?
C5 C6 C7 C8 3.3(19) . . . . ?
C6 C7 C8 C3 -2.4(17) . . . . ?
C6 C7 C8 C9 175.8(10) . . . . ?
C4 C3 C8 C7 1.4(15) . . . . ?
C2 C3 C8 C7 -179.2(10) . . . . ?
C4 C3 C8 C9 -176.8(9) . . . . ?
C2 C3 C8 C9 2.6(15) . . . . ?
C7 C8 C9 O2 3.4(15) . . . . ?
C3 C8 C9 O2 -178.4(9) . . . . ?
C7 C8 C9 C10 -177.1(9) . . . . ?
C3 C8 C9 C10 1.1(13) . . . . ?
N1 C1 C10 C11 -2.6(12) . . . . ?
C2 C1 C10 C11 177.9(10) . . . . ?
N1 C1 C10 C9 -179.7(9) . . . . ?
C2 C1 C10 C9 0.8(16) . . . . ?
O2 C9 C10 C1 176.7(10) . . . . ?
C8 C9 C10 C1 -2.8(14) . . . . ?
O2 C9 C10 C11 0.3(17) . . . . ?
C8 C9 C10 C11 -179.2(10) . . . . ?
C1 C10 C11 C12 3.3(11) . . . . ?
C9 C10 C11 C12 -179.9(10) . . . . ?
C1 C10 C11 C20 179.4(9) . . . . ?
C9 C10 C11 C20 -3.8(17) . . . . ?
C10 C11 C12 N1 -2.8(11) . . . . ?
C20 C11 C12 N1 -178.9(9) . . . . ?
C10 C11 C12 C13 177.0(11) . . . . ?
C20 C11 C12 C13 0.9(18) . . . . ?
N1 C12 C13 C14 -137.0(9) . . . . ?
C11 C12 C13 C14 43.2(17) . . . . ?
N1 C12 C13 C19 44.2(14) . . . . ?
C11 C12 C13 C19 -135.6(11) . . . . ?
C19 C13 C14 C15 0.4(15) . . . . ?
C12 C13 C14 C15 -178.4(10) . . . . ?
C13 C14 C15 C16 -0.6(16) . . . . ?
C14 C15 C16 C18 -0.3(16) . . . . ?
C14 C15 C16 C17 178.7(12) . . . . ?
C18 C16 C17 F3 -38(2) . . . . ?
C15 C16 C17 F3 142.8(13) . . . . ?
C18 C16 C17 F1 87.7(16) . . . . ?
C15 C16 C17 F1 -91.3(16) . . . . ?
C18 C16 C17 F2 -158.0(12) . . . . ?
C15 C16 C17 F2 23(2) . . . . ?
C15 C16 C18 C19 1.4(16) . . . . ?
C17 C16 C18 C19 -177.6(12) . . . . ?
C16 C18 C19 C13 -1.6(16) . . . . ?
C14 C13 C19 C18 0.6(15) . . . . ?
C12 C13 C19 C18 179.5(10) . . . . ?
C12 C11 C20 C21 121.8(10) . . . . ?
C10 C11 C20 C21 -53.6(13) . . . . ?
C12 C11 C20 C25 -107.2(11) . . . . ?
C10 C11 C20 C25 77.5(12) . . . . ?
C11 C20 C21 O3 -36.0(13) . . . . ?
C25 C20 C21 O3 -164.9(10) . . . . ?
C11 C20 C21 N2 147.4(8) . . . . ?
C25 C20 C21 N2 18.5(12) . . . . ?
C11 C20 C25 O4 34.4(14) . . . . ?
C21 C20 C25 O4 164.1(10) . . . . ?
C11 C20 C25 N3 -148.2(9) . . . . ?
C21 C20 C25 N3 -18.5(13) . . . . ?
C10 C1 N1 C12 0.8(12) . . . . ?
C2 C1 N1 C12 -179.7(10) . . . . ?
C11 C12 N1 C1 1.3(11) . . . . ?
C13 C12 N1 C1 -178.6(9) . . . . ?
O3 C21 N2 C23 174.4(10) . . . . ?
C20 C21 N2 C23 -9.0(14) . . . . ?
O3 C21 N2 C22 -2.4(14) . . . . ?
C20 C21 N2 C22 174.3(8) . . . . ?
O5 C23 N2 C21 -177.6(10) . . . . ?
N3 C23 N2 C21 -1.7(15) . . . . ?
O5 C23 N2 C22 -0.8(15) . . . . ?
N3 C23 N2 C22 175.1(9) . . . . ?
O4 C25 N3 C23 -173.7(11) . . . . ?
C20 C25 N3 C23 8.9(15) . . . . ?
O4 C25 N3 C24 5.2(16) . . . . ?
C20 C25 N3 C24 -172.2(9) . . . . ?
O5 C23 N3 C25 177.6(11) . . . . ?
N2 C23 N3 C25 1.7(16) . . . . ?
O5 C23 N3 C24 -1.3(16) . . . . ?
N2 C23 N3 C24 -177.3(9) . . . . ?

_refine_diff_density_max         0.392
_refine_diff_density_min         -0.386
_refine_diff_density_rms         0.072


# start Validation Reply Form

_vrf_THETM01_M_a                 
;
PROBLEM: The value of sine(theta_max)/wavelength is less than 0.550
RESPONSE: The crystal quality is poor and higher angle reflections
are very weak. The reflections above 23 degrees are omitted from
refinement for better R factor
;
_vrf_PLAT023_M_a                 
;
PROBLEM: Resolution (too) Low [sin(theta)/Lambda < 0.6]..      22.49 Degree
RESPONSE: as above
;
_vrf_RINTA01_M_a                 
;
PROBLEM: The value of Rint is greater than 0.18
RESPONSE: The crystal is weakly diffracting. Hence intensity of
observed reflections are very low. This caused higher values for Rint.
;
_vrf_PLAT020_M_a                 
;
PROBLEM: The Value of Rint is Greater Than 0.12 .........      0.233 Report
RESPONSE: The crystal is weakly diffracting at high angles as it
was very small c observed reflections are very low. This caused higher
values for Rint.
;
_vrf_PLAT340_M_a                 
;
PROBLEM: Low Bond Precision on  C-C Bonds ...............    0.01533 Ang.  
RESPONSE: Due to bad data quality, the C-C bond precision is low.
;
# end Validation Reply Form
