# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2022

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 2143849'
loop_
_audit_author_name
_audit_author_address
'Manasa P'
;Bangalore University
India
;
_audit_update_record             
;
2022-01-22 deposited with the CCDC.	2022-09-05 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         'C19 H19 Br N2 O4'
_chemical_formula_sum            'C19 H19 Br N2 O4'
_chemical_formula_weight         419.27

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   9.6335(9)
_cell_length_b                   10.5541(11)
_cell_length_c                   10.7463(9)
_cell_angle_alpha                74.967(4)
_cell_angle_beta                 66.776(4)
_cell_angle_gamma                66.004(4)
_cell_volume                     910.89(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4202
_cell_measurement_theta_min      4.898
_cell_measurement_theta_max      54.110

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.529
_exptl_crystal_F_000             428
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.400
_exptl_absorpt_coefficient_mu    2.283
_shelx_estimated_absorpt_T_min   0.395
_shelx_estimated_absorpt_T_max   0.462
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.395
_exptl_absorpt_correction_T_max  0.462
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker axs kappa apex2 CCD Diffractometer'
_diffrn_measurement_method       'ω and φ scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11198
_diffrn_reflns_av_unetI/netI     0.0664
_diffrn_reflns_av_R_equivalents  0.0558
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.077
_diffrn_reflns_theta_max         28.338
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.951
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.951
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.951
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4321
_reflns_number_gt                2857
_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       'APEX2 (Bruker, 2004)'
_computing_cell_refinement       'APEX2/SAINT (Bruker, 2004)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2004)'
_computing_structure_solution    'SIR92 (Altornare et al., 2014)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'

_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)+(0.1065P)²+0.6590P] 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         4321
_refine_ls_number_parameters     237
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1007
_refine_ls_R_factor_gt           0.0620
_refine_ls_wR_factor_ref         0.2054
_refine_ls_wR_factor_gt          0.1837
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_restrained_S_all      1.083
_refine_ls_shift/su_max          0.001
_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 0.4700(6) 0.0162(5) 0.1970(5) 0.0409(10) Uani 1 1 d . . . . .
H1 H 0.5808 -0.0102 0.1549 0.049 Uiso 1 1 calc R U . . .
C2 C 0.3900(7) -0.0651(5) 0.1952(5) 0.0489(12) Uani 1 1 d . . . . .
H2 H 0.4471 -0.1459 0.1523 0.059 Uiso 1 1 calc R U . . .
C3 C 0.2293(6) -0.0285(5) 0.2550(5) 0.0487(12) Uani 1 1 d . . . . .
H3 H 0.1767 -0.0841 0.2525 0.058 Uiso 1 1 calc R U . . .
C4 C 0.1425(6) 0.0896(5) 0.3194(5) 0.0451(11) Uani 1 1 d . . . . .
H4 H 0.0317 0.1145 0.3608 0.054 Uiso 1 1 calc R U . . .
C5 C 0.2232(5) 0.1705(4) 0.3216(4) 0.0309(8) Uani 1 1 d . . . . .
C6 C 0.3879(5) 0.1372(4) 0.2606(4) 0.0289(8) Uani 1 1 d . . . . .
C7 C 0.4719(5) 0.2293(4) 0.2649(4) 0.0336(9) Uani 1 1 d . . . . .
H7A H 0.4179 0.3247 0.2325 0.040 Uiso 1 1 calc R U . . .
H7B H 0.4614 0.2273 0.3589 0.040 Uiso 1 1 calc R U . . .
C8 C 0.6800(6) 0.2485(5) 0.0443(4) 0.0395(10) Uani 1 1 d . . . . .
H8A H 0.5945 0.2600 0.0116 0.047 Uiso 1 1 calc R U . . .
H18B H 0.7777 0.1829 -0.0085 0.047 Uiso 1 1 calc R U . . .
C9 C 0.7036(5) 0.3896(5) 0.0164(4) 0.0344(9) Uani 1 1 d . . . . .
C10 C 0.7619(5) 0.0937(4) 0.2310(4) 0.0346(9) Uani 1 1 d . . . . .
C11 C 0.7150(7) 0.0274(5) 0.3755(5) 0.0507(12) Uani 1 1 d . . . . .
H11A H 0.6823 0.0943 0.4363 0.076 Uiso 1 1 calc R U . . .
H11B H 0.8051 -0.0512 0.3902 0.076 Uiso 1 1 calc R U . . .
H11C H 0.6274 -0.0034 0.3925 0.076 Uiso 1 1 calc R U . . .
C12 C 0.7667(5) 0.5325(4) 0.1231(4) 0.0287(8) Uani 1 1 d . . . . .
C13 C 0.8091(5) 0.6235(4) 0.0087(4) 0.0384(10) Uani 1 1 d . . . . .
H13 H 0.8036 0.6160 -0.0735 0.046 Uiso 1 1 calc R U . . .
C14 C 0.8593(6) 0.7253(5) 0.0164(5) 0.0444(11) Uani 1 1 d . . . . .
H14 H 0.8903 0.7846 -0.0615 0.053 Uiso 1 1 calc R U . . .
C15 C 0.8642(6) 0.7405(4) 0.1373(5) 0.0429(11) Uani 1 1 d . . . . .
H15 H 0.8983 0.8097 0.1412 0.051 Uiso 1 1 calc R U . . .
C16 C 0.8195(5) 0.6548(4) 0.2507(5) 0.0380(9) Uani 1 1 d . . . . .
H16 H 0.8223 0.6666 0.3324 0.046 Uiso 1 1 calc R U . . .
C17 C 0.7687(5) 0.5481(4) 0.2488(4) 0.0300(8) Uani 1 1 d . . . . .
C18 C 0.7291(5) 0.4525(4) 0.3725(4) 0.0305(8) Uani 1 1 d . . . . .
C19 C 0.6805(7) 0.4064(5) 0.6092(4) 0.0493(12) Uani 1 1 d . . . . .
H19A H 0.6546 0.4537 0.6848 0.074 Uiso 1 1 calc R U . . .
H19B H 0.7760 0.3258 0.6046 0.074 Uiso 1 1 calc R U . . .
H19C H 0.5930 0.3776 0.6211 0.074 Uiso 1 1 calc R U . . .
N1 N 0.7248(4) 0.4216(3) 0.1192(3) 0.0320(7) Uani 1 1 d . . . . .
H1N4 H 0.7106 0.3658 0.1935 0.038 Uiso 1 1 calc R U . . .
N2 N 0.6416(4) 0.1889(4) 0.1840(3) 0.0316(7) Uani 1 1 d . . . . .
O1 O 0.7072(4) 0.4988(3) 0.4855(3) 0.0406(7) Uani 1 1 d . . . . .
O2 O 0.7147(5) 0.3430(3) 0.3774(3) 0.0473(8) Uani 1 1 d . . . . .
O3 O 0.7031(5) 0.4606(4) -0.0928(3) 0.0530(9) Uani 1 1 d . . . . .
O4 O 0.9018(4) 0.0659(4) 0.1587(4) 0.0518(8) Uani 1 1 d . . . . .
Br1 Br 0.10480(7) 0.33124(6) 0.41068(6) 0.0627(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 C2 1.374(6) . ?
C1 C6 1.389(6) . ?
C1 H1 0.9300 . ?
C2 C3 1.347(7) . ?
C2 H2 0.9300 . ?
C3 C4 1.369(7) . ?
C3 H3 0.9300 . ?
C4 C5 1.378(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.384(6) . ?
C5 Br1 1.871(4) . ?
C6 C7 1.515(5) . ?
C7 N2 1.454(5) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 N2 1.431(5) . ?
C8 C9 1.532(6) . ?
C8 H8A 0.9700 . ?
C8 H18B 0.9700 . ?
C9 O3 1.218(5) . ?
C9 N1 1.343(5) . ?
C10 O4 1.215(5) . ?
C10 N2 1.364(5) . ?
C10 C11 1.498(6) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 C13 1.383(5) . ?
C12 N1 1.398(5) . ?
C12 C17 1.411(5) . ?
C13 C14 1.376(6) . ?
C13 H13 0.9300 . ?
C14 C15 1.371(7) . ?
C14 H14 0.9300 . ?
C15 C16 1.349(6) . ?
C15 H15 0.9300 . ?
C16 C17 1.405(6) . ?
C16 H16 0.9300 . ?
C17 C18 1.466(5) . ?
C18 O2 1.204(5) . ?
C18 O1 1.334(5) . ?
C19 O1 1.431(5) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
N1 H1N4 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
C2 C1 C6 121.0(4) . . ?
C2 C1 H1 119.5 . . ?
C6 C1 H1 119.5 . . ?
C3 C2 C1 120.5(5) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C2 C3 C4 120.9(4) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
C3 C4 C5 118.5(4) . . ?
C3 C4 H4 120.8 . . ?
C5 C4 H4 120.8 . . ?
C4 C5 C6 122.5(4) . . ?
C4 C5 Br1 118.5(3) . . ?
C6 C5 Br1 119.0(3) . . ?
C5 C6 C1 116.6(4) . . ?
C5 C6 C7 120.8(4) . . ?
C1 C6 C7 122.6(4) . . ?
N2 C7 C6 114.2(3) . . ?
N2 C7 H7A 108.7 . . ?
C6 C7 H7A 108.7 . . ?
N2 C7 H7B 108.7 . . ?
C6 C7 H7B 108.7 . . ?
H7A C7 H7B 107.6 . . ?
N2 C8 C9 115.6(3) . . ?
N2 C8 H8A 108.4 . . ?
C9 C8 H8A 108.4 . . ?
N2 C8 H18B 108.4 . . ?
C9 C8 H18B 108.4 . . ?
H8A C8 H18B 107.4 . . ?
O3 C9 N1 126.2(4) . . ?
O3 C9 C8 119.4(4) . . ?
N1 C9 C8 114.4(3) . . ?
O4 C10 N2 121.0(4) . . ?
O4 C10 C11 121.6(4) . . ?
N2 C10 C11 117.4(4) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C13 C12 N1 122.4(4) . . ?
C13 C12 C17 119.7(4) . . ?
N1 C12 C17 117.8(3) . . ?
C14 C13 C12 120.0(4) . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C15 C14 C13 121.0(4) . . ?
C15 C14 H14 119.5 . . ?
C13 C14 H14 119.5 . . ?
C16 C15 C14 119.8(4) . . ?
C16 C15 H15 120.1 . . ?
C14 C15 H15 120.1 . . ?
C15 C16 C17 121.8(4) . . ?
C15 C16 H16 119.1 . . ?
C17 C16 H16 119.1 . . ?
C16 C17 C12 117.7(4) . . ?
C16 C17 C18 120.1(4) . . ?
C12 C17 C18 122.1(3) . . ?
O2 C18 O1 121.0(3) . . ?
O2 C18 C17 125.8(4) . . ?
O1 C18 C17 113.1(3) . . ?
O1 C19 H19A 109.5 . . ?
O1 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O1 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C9 N1 C12 129.5(3) . . ?
C9 N1 H1N4 115.2 . . ?
C12 N1 H1N4 115.2 . . ?
C10 N2 C8 119.3(4) . . ?
C10 N2 C7 124.2(3) . . ?
C8 N2 C7 116.4(3) . . ?
C18 O1 C19 116.5(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 0.3(7) . . . . ?
C1 C2 C3 C4 -0.4(7) . . . . ?
C2 C3 C4 C5 0.1(7) . . . . ?
C3 C4 C5 C6 0.3(6) . . . . ?
C3 C4 C5 Br1 -179.6(3) . . . . ?
C4 C5 C6 C1 -0.4(6) . . . . ?
Br1 C5 C6 C1 179.5(3) . . . . ?
C4 C5 C6 C7 179.8(4) . . . . ?
Br1 C5 C6 C7 -0.3(5) . . . . ?
C2 C1 C6 C5 0.1(6) . . . . ?
C2 C1 C6 C7 179.9(4) . . . . ?
C5 C6 C7 N2 -173.6(3) . . . . ?
C1 C6 C7 N2 6.6(5) . . . . ?
N2 C8 C9 O3 -164.8(4) . . . . ?
N2 C8 C9 N1 15.8(6) . . . . ?
N1 C12 C13 C14 -175.8(4) . . . . ?
C17 C12 C13 C14 2.7(6) . . . . ?
C12 C13 C14 C15 -1.7(7) . . . . ?
C13 C14 C15 C16 0.0(7) . . . . ?
C14 C15 C16 C17 0.6(7) . . . . ?
C15 C16 C17 C12 0.3(6) . . . . ?
C15 C16 C17 C18 176.8(4) . . . . ?
C13 C12 C17 C16 -2.0(6) . . . . ?
N1 C12 C17 C16 176.5(4) . . . . ?
C13 C12 C17 C18 -178.4(4) . . . . ?
N1 C12 C17 C18 0.2(6) . . . . ?
C16 C17 C18 O2 -164.8(4) . . . . ?
C12 C17 C18 O2 11.5(7) . . . . ?
C16 C17 C18 O1 15.9(5) . . . . ?
C12 C17 C18 O1 -167.8(4) . . . . ?
O3 C9 N1 C12 -7.2(7) . . . . ?
C8 C9 N1 C12 172.2(4) . . . . ?
C13 C12 N1 C9 -6.4(7) . . . . ?
C17 C12 N1 C9 175.1(4) . . . . ?
O4 C10 N2 C8 4.9(6) . . . . ?
C11 C10 N2 C8 -176.3(4) . . . . ?
O4 C10 N2 C7 -178.9(4) . . . . ?
C11 C10 N2 C7 -0.1(6) . . . . ?
C9 C8 N2 C10 -95.3(5) . . . . ?
C9 C8 N2 C7 88.3(4) . . . . ?
C6 C7 N2 C10 -87.6(4) . . . . ?
C6 C7 N2 C8 88.6(4) . . . . ?
O2 C18 O1 C19 5.4(6) . . . . ?
C17 C18 O1 C19 -175.3(4) . . . . ?

_refine_diff_density_max         0.463
_refine_diff_density_min         -0.845
_refine_diff_density_rms         0.104

####################################################################### 
# 
# 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_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2143852'
loop_
_audit_author_name
_audit_author_address
'Manasa Purushotham'
;Bangalore University 
India
;
_audit_update_record             
;
2022-01-22 deposited with the CCDC.	2022-09-05 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         'C19 H19 I N2 O4'
_chemical_formula_sum            'C19 H19 I N2 O4'
_chemical_formula_weight         466.26

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'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   8.7203(5)
_cell_length_b                   9.1769(7)
_cell_length_c                   13.4991(9)
_cell_angle_alpha                74.064(3)
_cell_angle_beta                 88.893(3)
_cell_angle_gamma                71.669(3)
_cell_volume                     983.38(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6941
_cell_measurement_theta_min      4.875
_cell_measurement_theta_max      56.602

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.575
_exptl_crystal_F_000             464
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    1.653
_shelx_estimated_absorpt_T_min   0.595
_shelx_estimated_absorpt_T_max   0.733
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.595
_exptl_absorpt_correction_T_max  0.733
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker axs kappa apex2 CCD Diffractometer'
_diffrn_measurement_method       'ω and φ scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10764
_diffrn_reflns_av_unetI/netI     0.0284
_diffrn_reflns_av_R_equivalents  0.0225
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.438
_diffrn_reflns_theta_max         28.368
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.971
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.971
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.971
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             4784
_reflns_number_gt                4164
_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       'APEX2 (Bruker, 2004)'
_computing_cell_refinement       'APEX2/SAINT (Bruker, 2004)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2004)'
_computing_structure_solution    'SIR92 (Altornare et al., 2014)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'

_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)+(0.0451P)²+0.6109P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.0216(13)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4784
_refine_ls_number_parameters     242
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0376
_refine_ls_R_factor_gt           0.0309
_refine_ls_wR_factor_ref         0.0867
_refine_ls_wR_factor_gt          0.0825
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_restrained_S_all      1.010
_refine_ls_shift/su_max          0.001
_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 0.2048(5) 0.7195(5) 0.5092(2) 0.0596(8) Uani 1 1 d . . . . .
H1 H 0.1168 0.6936 0.4904 0.071 Uiso 1 1 calc R U . . .
C2 C 0.2097(5) 0.7545(5) 0.6021(3) 0.0685(10) Uani 1 1 d . . . . .
H2 H 0.1255 0.7518 0.6451 0.082 Uiso 1 1 calc R U . . .
C3 C 0.3382(5) 0.7930(5) 0.6308(2) 0.0649(9) Uani 1 1 d . . . . .
H3 H 0.3413 0.8164 0.6934 0.078 Uiso 1 1 calc R U . . .
C4 C 0.4631(4) 0.7974(4) 0.5671(2) 0.0530(7) Uani 1 1 d . . . . .
H4 H 0.5501 0.8244 0.5862 0.064 Uiso 1 1 calc R U . . .
C5 C 0.4581(3) 0.7612(3) 0.47418(19) 0.0396(5) Uani 1 1 d . . . . .
C6 C 0.3289(4) 0.7221(3) 0.4435(2) 0.0419(6) Uani 1 1 d . . . . .
C7 C 0.3246(4) 0.6836(4) 0.3412(2) 0.0483(7) Uani 1 1 d . . . . .
H7A H 0.3569 0.7615 0.2883 0.058 Uiso 1 1 calc R U . . .
H7B H 0.4031 0.5792 0.3472 0.058 Uiso 1 1 calc R U . . .
C8 C 0.0815(5) 0.9733(4) 0.2303(3) 0.0696(10) Uani 1 1 d . . . . .
H8A H -0.0146 1.0591 0.1981 0.104 Uiso 1 1 calc R U . . .
H8B H 0.1658 0.9690 0.1833 0.104 Uiso 1 1 calc R U . . .
H8C H 0.1159 0.9912 0.2918 0.104 Uiso 1 1 calc R U . . .
C9 C 0.0461(4) 0.8179(4) 0.2578(2) 0.0452(6) Uani 1 1 d . . . . .
C10 C 0.1314(4) 0.5331(4) 0.3383(2) 0.0489(7) Uani 1 1 d . . . . .
H10A H 0.0197 0.5553 0.3561 0.059 Uiso 1 1 calc R U . . .
H10B H 0.1993 0.4646 0.4002 0.059 Uiso 1 1 calc R U . . .
C11 C 0.1555(4) 0.4409(3) 0.2589(2) 0.0451(6) Uani 1 1 d . . . . .
C12 C 0.2152(3) 0.4678(3) 0.0755(2) 0.0401(5) Uani 1 1 d . . . . .
C13 C 0.2707(3) 0.5583(3) -0.0097(2) 0.0433(6) Uani 1 1 d . . . . .
C14 C 0.2838(4) 0.5142(4) -0.1013(3) 0.0577(8) Uani 1 1 d . . . . .
H14 H 0.3239 0.5714 -0.1578 0.069 Uiso 1 1 calc R U . . .
C15 C 0.2377(5) 0.3862(5) -0.1089(3) 0.0686(10) Uani 1 1 d . . . . .
H15 H 0.2458 0.3579 -0.1704 0.082 Uiso 1 1 calc R U . . .
C16 C 0.1810(5) 0.3028(4) -0.0264(3) 0.0650(9) Uani 1 1 d . . . . .
H16 H 0.1482 0.2184 -0.0325 0.078 Uiso 1 1 calc R U . . .
C17 C 0.1699(4) 0.3387(4) 0.0669(3) 0.0544(7) Uani 1 1 d . . . . .
H17 H 0.1329 0.2777 0.1232 0.065 Uiso 1 1 calc R U . . .
C18 C 0.3103(3) 0.7025(3) -0.0063(2) 0.0454(6) Uani 1 1 d . . . . .
C19 C 0.4127(5) 0.9067(4) -0.0956(3) 0.0672(9) Uani 1 1 d . . . . .
H19A H 0.3151 0.9966 -0.1077 0.101 Uiso 1 1 calc R U . . .
H19B H 0.4817 0.9249 -0.1507 0.101 Uiso 1 1 calc R U . . .
H19C H 0.4678 0.8935 -0.0312 0.101 Uiso 1 1 calc R U . . .
N1 N 0.1666(3) 0.6833(3) 0.30847(17) 0.0428(5) Uani 1 1 d . . . . .
N2 N 0.2004(3) 0.5123(3) 0.16747(18) 0.0427(5) Uani 1 1 d . . . . .
O1 O -0.0845(3) 0.8108(3) 0.23411(19) 0.0595(6) Uani 1 1 d . . . . .
O2 O 0.2889(4) 0.7611(3) 0.06495(19) 0.0684(7) Uani 1 1 d . . . . .
O3 O 0.3728(3) 0.7641(3) -0.09129(16) 0.0575(5) Uani 1 1 d . . . . .
O4 O 0.1330(4) 0.3124(3) 0.2819(2) 0.0758(8) Uani 1 1 d . . . . .
I1 I 0.65092(2) 0.77240(2) 0.37991(2) 0.05087(10) Uani 1 1 d . . . . .
H2N H 0.209(4) 0.597(4) 0.158(3) 0.044(8) Uiso 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 C2 1.381(4) . ?
C1 C6 1.388(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.369(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.378(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.388(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.386(4) . ?
C5 I1 2.100(3) . ?
C6 C7 1.521(4) . ?
C7 N1 1.456(4) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.499(4) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 O1 1.214(4) . ?
C9 N1 1.359(4) . ?
C10 N1 1.453(4) . ?
C10 C11 1.513(4) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 O4 1.212(4) . ?
C11 N2 1.343(4) . ?
C12 C17 1.395(4) . ?
C12 C13 1.397(4) . ?
C12 N2 1.401(3) . ?
C13 C14 1.395(4) . ?
C13 C18 1.482(4) . ?
C14 C15 1.385(5) . ?
C14 H14 0.9300 . ?
C15 C16 1.349(6) . ?
C15 H15 0.9300 . ?
C16 C17 1.381(5) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 O2 1.210(4) . ?
C18 O3 1.321(4) . ?
C19 O3 1.442(4) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
N2 H2N 0.78(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 121.2(3) . . ?
C2 C1 H1 119.4 . . ?
C6 C1 H1 119.4 . . ?
C3 C2 C1 120.2(3) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C2 C3 C4 120.1(3) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C3 C4 C5 119.5(3) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
C4 C5 C6 121.3(3) . . ?
C4 C5 I1 117.6(2) . . ?
C6 C5 I1 121.07(19) . . ?
C5 C6 C1 117.8(2) . . ?
C5 C6 C7 120.7(2) . . ?
C1 C6 C7 121.5(3) . . ?
N1 C7 C6 113.9(2) . . ?
N1 C7 H7A 108.8 . . ?
C6 C7 H7A 108.8 . . ?
N1 C7 H7B 108.8 . . ?
C6 C7 H7B 108.8 . . ?
H7A C7 H7B 107.7 . . ?
C9 C8 H8A 109.5 . . ?
C9 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C9 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
O1 C9 N1 120.6(3) . . ?
O1 C9 C8 121.6(3) . . ?
N1 C9 C8 117.8(3) . . ?
N1 C10 C11 116.5(2) . . ?
N1 C10 H10A 108.2 . . ?
C11 C10 H10A 108.2 . . ?
N1 C10 H10B 108.2 . . ?
C11 C10 H10B 108.2 . . ?
H10A C10 H10B 107.3 . . ?
O4 C11 N2 126.0(3) . . ?
O4 C11 C10 118.6(3) . . ?
N2 C11 C10 115.4(2) . . ?
C17 C12 C13 119.8(3) . . ?
C17 C12 N2 121.0(3) . . ?
C13 C12 N2 119.2(2) . . ?
C14 C13 C12 118.9(3) . . ?
C14 C13 C18 119.3(3) . . ?
C12 C13 C18 121.8(2) . . ?
C15 C14 C13 120.7(3) . . ?
C15 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C16 C15 C14 119.4(3) . . ?
C16 C15 H15 120.3 . . ?
C14 C15 H15 120.3 . . ?
C15 C16 C17 122.2(3) . . ?
C15 C16 H16 118.9 . . ?
C17 C16 H16 118.9 . . ?
C16 C17 C12 119.0(3) . . ?
C16 C17 H17 120.5 . . ?
C12 C17 H17 120.5 . . ?
O2 C18 O3 122.1(3) . . ?
O2 C18 C13 125.2(3) . . ?
O3 C18 C13 112.7(3) . . ?
O3 C19 H19A 109.5 . . ?
O3 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O3 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C9 N1 C10 118.1(2) . . ?
C9 N1 C7 123.4(3) . . ?
C10 N1 C7 118.3(3) . . ?
C11 N2 C12 129.3(2) . . ?
C11 N2 H2N 120(2) . . ?
C12 N2 H2N 110(2) . . ?
C18 O3 C19 116.6(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 0.1(6) . . . . ?
C1 C2 C3 C4 0.1(6) . . . . ?
C2 C3 C4 C5 -0.5(6) . . . . ?
C3 C4 C5 C6 0.6(5) . . . . ?
C3 C4 C5 I1 179.4(3) . . . . ?
C4 C5 C6 C1 -0.4(4) . . . . ?
I1 C5 C6 C1 -179.0(2) . . . . ?
C4 C5 C6 C7 179.7(3) . . . . ?
I1 C5 C6 C7 1.0(4) . . . . ?
C2 C1 C6 C5 0.0(5) . . . . ?
C2 C1 C6 C7 179.9(3) . . . . ?
C5 C6 C7 N1 -165.9(3) . . . . ?
C1 C6 C7 N1 14.2(4) . . . . ?
N1 C10 C11 O4 177.5(3) . . . . ?
N1 C10 C11 N2 -2.7(4) . . . . ?
C17 C12 C13 C14 -1.8(4) . . . . ?
N2 C12 C13 C14 -179.4(3) . . . . ?
C17 C12 C13 C18 176.1(3) . . . . ?
N2 C12 C13 C18 -1.6(4) . . . . ?
C12 C13 C14 C15 2.1(5) . . . . ?
C18 C13 C14 C15 -175.8(3) . . . . ?
C13 C14 C15 C16 -0.6(5) . . . . ?
C14 C15 C16 C17 -1.3(6) . . . . ?
C15 C16 C17 C12 1.6(5) . . . . ?
C13 C12 C17 C16 0.0(4) . . . . ?
N2 C12 C17 C16 177.6(3) . . . . ?
C14 C13 C18 O2 172.5(3) . . . . ?
C12 C13 C18 O2 -5.3(5) . . . . ?
C14 C13 C18 O3 -7.2(4) . . . . ?
C12 C13 C18 O3 174.9(3) . . . . ?
O1 C9 N1 C10 -3.4(4) . . . . ?
C8 C9 N1 C10 178.1(3) . . . . ?
O1 C9 N1 C7 -178.6(3) . . . . ?
C8 C9 N1 C7 2.9(4) . . . . ?
C11 C10 N1 C9 87.4(3) . . . . ?
C11 C10 N1 C7 -97.2(3) . . . . ?
C6 C7 N1 C9 83.2(3) . . . . ?
C6 C7 N1 C10 -91.9(3) . . . . ?
O4 C11 N2 C12 7.4(5) . . . . ?
C10 C11 N2 C12 -172.3(3) . . . . ?
C17 C12 N2 C11 4.8(5) . . . . ?
C13 C12 N2 C11 -177.5(3) . . . . ?
O2 C18 O3 C19 -0.8(5) . . . . ?
C13 C18 O3 C19 179.0(3) . . . . ?

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
C17 H17 O4 0.93 2.25 2.866(4) 123.0 .
C19 H19A O1 0.96 2.51 3.359(5) 146.9 2_575

_refine_diff_density_max         0.838
_refine_diff_density_min         -0.667
_refine_diff_density_rms         0.077

####################################################################### 
# 
# 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_shelx_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 2143850'
loop_
_audit_author_name
_audit_author_address
'Manasa Purushotham'
;Bangalore University 
India
;
_audit_update_record             
;
2022-01-22 deposited with the CCDC.	2022-09-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H19 Cl N2 O4'
_chemical_formula_weight         374.81

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   9.5811(3)
_cell_length_b                   10.4629(4)
_cell_length_c                   10.6719(4)
_cell_angle_alpha                74.919(2)
_cell_angle_beta                 66.039(2)
_cell_angle_gamma                64.784(2)
_cell_volume                     879.53(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9869
_cell_measurement_theta_min      2.50
_cell_measurement_theta_max      30.48

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLORLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.415
_exptl_crystal_F_000             392
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.245
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(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            19411
_diffrn_reflns_av_unetI/netI     0.0192
_diffrn_reflns_av_R_equivalents  0.0233
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.100
_diffrn_reflns_theta_max         30.504
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5336
_reflns_number_gt                4895
_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-2018/3 (Sheldrick, 2018)'
_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)+(0.0542P)²+0.5513P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5336
_refine_ls_number_parameters     239
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0414
_refine_ls_R_factor_gt           0.0381
_refine_ls_wR_factor_ref         0.1116
_refine_ls_wR_factor_gt          0.1091
_refine_ls_goodness_of_fit_ref   1.071
_refine_ls_restrained_S_all      1.071
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.001

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 0.28344(14) 0.82245(12) 0.17561(12) 0.0145(2) Uani 1 1 d . . . . .
C2 C 0.11383(14) 0.85973(12) 0.23646(12) 0.0134(2) Uani 1 1 d . . . . .
C3 C 0.02693(15) 0.98233(13) 0.30404(13) 0.0168(2) Uani 1 1 d . . . . .
H3 H -0.086157 1.009818 0.346154 0.020 Uiso 1 1 calc R U . . .
C4 C 0.10625(16) 1.06450(13) 0.30970(14) 0.0199(2) Uani 1 1 d . . . . .
H4 H 0.045868 1.146590 0.354326 0.024 Uiso 1 1 calc R U . . .
C5 C 0.27505(16) 1.02413(13) 0.24892(14) 0.0200(2) Uani 1 1 d . . . . .
H5 H 0.327920 1.078591 0.253585 0.024 Uiso 1 1 calc R U . . .
C6 C 0.36525(15) 0.90211(13) 0.18097(13) 0.0181(2) Uani 1 1 d . . . . .
H6 H 0.478469 0.874307 0.139806 0.022 Uiso 1 1 calc R U . . .
C7 C 0.03118(14) 0.76851(12) 0.22791(12) 0.0148(2) Uani 1 1 d . . . . .
H7A H 0.041293 0.774260 0.132590 0.018 Uiso 1 1 calc R U . . .
H7B H 0.088186 0.670364 0.256605 0.018 Uiso 1 1 calc R U . . .
C8 C -0.26658(14) 0.90793(12) 0.26765(12) 0.0148(2) Uani 1 1 d . . . . .
C9 C -0.22033(17) 0.97786(14) 0.12178(13) 0.0204(2) Uani 1 1 d . . . . .
H9A H -0.103265 0.941797 0.079141 0.031 Uiso 1 1 calc R U . . .
H9B H -0.269363 0.957517 0.070421 0.031 Uiso 1 1 calc R U . . .
H9C H -0.258932 1.078734 0.123016 0.031 Uiso 1 1 calc R U . . .
C10 C -0.17974(15) 0.74703(13) 0.45509(12) 0.0160(2) Uani 1 1 d . . . . .
H10A H -0.280036 0.813927 0.510152 0.019 Uiso 1 1 calc R U . . .
H10B H -0.092829 0.734431 0.487056 0.019 Uiso 1 1 calc R U . . .
C11 C -0.20091(14) 0.60448(12) 0.48161(12) 0.0141(2) Uani 1 1 d . . . . .
C12 C -0.26506(13) 0.46349(11) 0.37084(12) 0.0127(2) Uani 1 1 d . . . . .
C13 C -0.30970(14) 0.37109(12) 0.48784(12) 0.0157(2) Uani 1 1 d . . . . .
H13 H -0.303075 0.377179 0.570525 0.019 Uiso 1 1 calc R U . . .
C14 C -0.36383(15) 0.27046(12) 0.48007(13) 0.0178(2) Uani 1 1 d . . . . .
H14 H -0.394798 0.210518 0.558442 0.021 Uiso 1 1 calc R U . . .
C15 C -0.37249(15) 0.25782(12) 0.35722(14) 0.0178(2) Uani 1 1 d . . . . .
H15 H -0.410348 0.190881 0.353679 0.021 Uiso 1 1 calc R U . . .
C16 C -0.32418(15) 0.34593(12) 0.23996(13) 0.0161(2) Uani 1 1 d . . . . .
H16 H -0.327539 0.336218 0.157152 0.019 Uiso 1 1 calc R U . . .
C17 C -0.27031(13) 0.44952(11) 0.24451(12) 0.0128(2) Uani 1 1 d . . . . .
C18 C -0.22832(14) 0.54696(12) 0.11846(12) 0.0135(2) Uani 1 1 d . . . . .
C19 C -0.18793(17) 0.60160(14) -0.11845(12) 0.0199(2) Uani 1 1 d . . . . .
H19A H -0.176897 0.561717 -0.194953 0.030 Uiso 1 1 calc R U . . .
H19B H -0.280772 0.689150 -0.104563 0.030 Uiso 1 1 calc R U . . .
H19C H -0.090561 0.619466 -0.137426 0.030 Uiso 1 1 calc R U . . .
N1 N -0.22080(13) 0.57322(11) 0.37541(10) 0.01391(18) Uani 1 1 d . . . . .
N2 N -0.14152(12) 0.80925(11) 0.31230(10) 0.01395(18) Uani 1 1 d . . . . .
O1 O -0.20224(12) 0.53175(10) 0.59180(9) 0.02009(19) Uani 1 1 d . . . . .
O2 O -0.21139(11) 0.50275(9) 0.00466(9) 0.01677(17) Uani 1 1 d . . . . .
O3 O -0.21183(12) 0.65726(10) 0.11561(9) 0.01985(19) Uani 1 1 d . . . . .
O4 O -0.40996(11) 0.93693(10) 0.34314(10) 0.02042(19) Uani 1 1 d . . . . .
Cl1 Cl 0.39730(4) 0.66984(3) 0.09003(3) 0.02014(8) Uani 1 1 d . . . . .
H1 H -0.216(2) 0.633(2) 0.303(2) 0.026(5) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.3894(16) . ?
C1 C2 1.3961(16) . ?
C1 Cl1 1.7433(12) . ?
C2 C3 1.3937(16) . ?
C2 C7 1.5147(15) . ?
C3 C4 1.3933(16) . ?
C4 C5 1.3868(18) . ?
C5 C6 1.3911(18) . ?
C7 N2 1.4557(15) . ?
C8 O4 1.2253(15) . ?
C8 N2 1.3720(15) . ?
C8 C9 1.5094(17) . ?
C10 N2 1.4539(15) . ?
C10 C11 1.5289(16) . ?
C11 O1 1.2217(14) . ?
C11 N1 1.3598(15) . ?
C12 N1 1.4003(14) . ?
C12 C13 1.4025(15) . ?
C12 C17 1.4161(16) . ?
C13 C14 1.3892(16) . ?
C14 C15 1.3897(18) . ?
C15 C16 1.3867(17) . ?
C16 C17 1.4028(15) . ?
C17 C18 1.4856(15) . ?
C18 O3 1.2211(14) . ?
C18 O2 1.3355(14) . ?
C19 O2 1.4483(15) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 122.52(11) . . ?
C6 C1 Cl1 118.64(9) . . ?
C2 C1 Cl1 118.84(9) . . ?
C3 C2 C1 117.21(10) . . ?
C3 C2 C7 122.54(10) . . ?
C1 C2 C7 120.25(10) . . ?
C4 C3 C2 121.26(11) . . ?
C5 C4 C3 120.14(11) . . ?
C4 C5 C6 119.95(11) . . ?
C1 C6 C5 118.92(11) . . ?
N2 C7 C2 113.75(9) . . ?
O4 C8 N2 121.12(11) . . ?
O4 C8 C9 121.56(11) . . ?
N2 C8 C9 117.32(10) . . ?
N2 C10 C11 115.55(9) . . ?
O1 C11 N1 126.10(11) . . ?
O1 C11 C10 119.98(10) . . ?
N1 C11 C10 113.90(10) . . ?
N1 C12 C13 122.21(10) . . ?
N1 C12 C17 118.42(10) . . ?
C13 C12 C17 119.33(10) . . ?
C14 C13 C12 119.92(11) . . ?
C15 C14 C13 121.14(11) . . ?
C16 C15 C14 119.40(11) . . ?
C15 C16 C17 120.91(11) . . ?
C16 C17 C12 119.26(10) . . ?
C16 C17 C18 119.20(10) . . ?
C12 C17 C18 121.46(10) . . ?
O3 C18 O2 121.97(10) . . ?
O3 C18 C17 125.15(10) . . ?
O2 C18 C17 112.88(10) . . ?
C11 N1 C12 129.28(10) . . ?
C8 N2 C10 119.06(10) . . ?
C8 N2 C7 124.09(10) . . ?
C10 N2 C7 116.72(10) . . ?
C18 O2 C19 114.91(9) . . ?

_refine_diff_density_max         0.770
_refine_diff_density_min         -0.806
_refine_diff_density_rms         0.063

####################################################################### 
# 
# 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_shelx_CCDC3
_database_code_depnum_ccdc_archive 'CCDC 2143851'
loop_
_audit_author_name
_audit_author_address
'Manasa Purushotham'
;Bangalore University 
India
;
_audit_update_record             
;
2022-01-22 deposited with the CCDC.	2022-09-05 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H19 F N2 O4'
_chemical_formula_weight         358.36

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   9.5349(6)
_cell_length_b                   10.5406(7)
_cell_length_c                   10.6231(7)
_cell_angle_alpha                76.135(3)
_cell_angle_beta                 66.751(3)
_cell_angle_gamma                64.827(3)
_cell_volume                     884.49(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    6961
_cell_measurement_theta_min      2.50
_cell_measurement_theta_max      29.07

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            'PALE YELLOW'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.346
_exptl_crystal_F_000             376
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.102
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(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            20252
_diffrn_reflns_av_unetI/netI     0.0252
_diffrn_reflns_av_R_equivalents  0.0293
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.094
_diffrn_reflns_theta_max         30.568
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5381
_reflns_number_gt                3557
_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-2018/3 (Sheldrick, 2018)'
_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)+(0.0735P)²+0.1521P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5381
_refine_ls_number_parameters     239
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0771
_refine_ls_R_factor_gt           0.0502
_refine_ls_wR_factor_ref         0.1589
_refine_ls_wR_factor_gt          0.1401
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_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 -0.12006(17) 0.15101(15) 0.26582(14) 0.0432(3) Uani 1 1 d . . . . .
C2 C -0.28790(19) 0.18705(17) 0.32234(16) 0.0523(4) Uani 1 1 d . . . . .
C3 C -0.3690(2) 0.1103(2) 0.3135(2) 0.0651(5) Uani 1 1 d . . . . .
H3 H -0.482752 0.139215 0.352562 0.078 Uiso 1 1 calc R U . . .
C4 C -0.2788(2) -0.0099(2) 0.2459(2) 0.0659(5) Uani 1 1 d . . . . .
H4 H -0.331045 -0.063447 0.238425 0.079 Uiso 1 1 calc R U . . .
C5 C -0.1117(2) -0.05067(19) 0.1895(2) 0.0656(5) Uani 1 1 d . . . . .
H5 H -0.050284 -0.132632 0.144421 0.079 Uiso 1 1 calc R U . . .
C6 C -0.03322(19) 0.02954(17) 0.19909(18) 0.0551(4) Uani 1 1 d . . . . .
H6 H 0.080454 0.000674 0.159634 0.066 Uiso 1 1 calc R U . . .
C7 C -0.04227(19) 0.24353(16) 0.27946(17) 0.0508(4) Uani 1 1 d . . . . .
H7A H -0.100731 0.340197 0.251287 0.061 Uiso 1 1 calc R U . . .
H7B H -0.055000 0.238926 0.375470 0.061 Uiso 1 1 calc R U . . .
C8 C 0.25539(19) 0.10460(16) 0.24185(16) 0.0486(3) Uani 1 1 d . . . . .
C9 C 0.2113(3) 0.0371(2) 0.38569(19) 0.0687(5) Uani 1 1 d . . . . .
H9A H 0.094286 0.075033 0.429534 0.103 Uiso 1 1 calc R U . . .
H9B H 0.247944 -0.062612 0.383355 0.103 Uiso 1 1 calc R U . . .
H9C H 0.263535 0.055794 0.436363 0.103 Uiso 1 1 calc R U . . .
C10 C 0.1707(2) 0.26597(17) 0.05716(15) 0.0506(4) Uani 1 1 d . . . . .
H10A H 0.082271 0.282377 0.024426 0.061 Uiso 1 1 calc R U . . .
H10B H 0.269235 0.197450 0.001707 0.061 Uiso 1 1 calc R U . . .
C11 C 0.19845(17) 0.40280(16) 0.03265(14) 0.0445(3) Uani 1 1 d . . . . .
C12 C 0.26431(16) 0.54089(14) 0.14711(14) 0.0416(3) Uani 1 1 d . . . . .
C13 C 0.30620(19) 0.63325(16) 0.03331(17) 0.0530(4) Uani 1 1 d . . . . .
H13 H 0.296334 0.629342 -0.049226 0.064 Uiso 1 1 calc R U . . .
C14 C 0.3624(2) 0.73057(16) 0.0435(2) 0.0602(4) Uani 1 1 d . . . . .
H14 H 0.390931 0.791088 -0.032859 0.072 Uiso 1 1 calc R U . . .
C15 C 0.3766(2) 0.73917(17) 0.1641(2) 0.0629(5) Uani 1 1 d . . . . .
H15 H 0.414791 0.804910 0.169400 0.076 Uiso 1 1 calc R U . . .
C16 C 0.3344(2) 0.65042(16) 0.27732(19) 0.0559(4) Uani 1 1 d . . . . .
H16 H 0.344072 0.656811 0.359105 0.067 Uiso 1 1 calc R U . . .
C17 C 0.27697(17) 0.55060(14) 0.27197(15) 0.0433(3) Uani 1 1 d . . . . .
C18 C 0.23726(18) 0.45386(15) 0.39563(14) 0.0462(3) Uani 1 1 d . . . . .
C19 C 0.2303(3) 0.3835(2) 0.62490(18) 0.0749(6) Uani 1 1 d . . . . .
H19A H 0.244026 0.412285 0.697035 0.112 Uiso 1 1 calc R U . . .
H19B H 0.121717 0.382344 0.654676 0.112 Uiso 1 1 calc R U . . .
H19C H 0.310045 0.290894 0.603212 0.112 Uiso 1 1 calc R U . . .
N1 N 0.13075(15) 0.20480(13) 0.19867(12) 0.0450(3) Uani 1 1 d . . . . .
N2 N 0.21568(16) 0.43539(13) 0.13997(13) 0.0457(3) Uani 1 1 d . . . . .
O1 O 0.19728(18) 0.35755(13) 0.40113(11) 0.0677(4) Uani 1 1 d . . . . .
O2 O 0.25286(16) 0.48094(12) 0.50429(11) 0.0598(3) Uani 1 1 d . . . . .
O3 O 0.20643(15) 0.47149(14) -0.07792(11) 0.0623(3) Uani 1 1 d . . . . .
O4 O 0.39754(14) 0.07296(14) 0.16620(14) 0.0669(3) Uani 1 1 d . . . . .
F1 F -0.37612(13) 0.30562(14) 0.39036(14) 0.0875(4) Uani 1 1 d . . . . .
H2 H 0.204(2) 0.3819(19) 0.2131(19) 0.055(5) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.377(2) . ?
C1 C2 1.378(2) . ?
C1 C7 1.5133(19) . ?
C2 F1 1.360(2) . ?
C2 C3 1.374(2) . ?
C3 C4 1.372(3) . ?
C4 C5 1.367(3) . ?
C5 C6 1.387(2) . ?
C7 N1 1.4498(19) . ?
C8 O4 1.2158(19) . ?
C8 N1 1.367(2) . ?
C8 C9 1.498(2) . ?
C10 N1 1.4536(19) . ?
C10 C11 1.519(2) . ?
C11 O3 1.2159(17) . ?
C11 N2 1.3521(18) . ?
C12 C13 1.3980(19) . ?
C12 N2 1.4015(17) . ?
C12 C17 1.409(2) . ?
C13 C14 1.385(2) . ?
C14 C15 1.368(3) . ?
C15 C16 1.372(2) . ?
C16 C17 1.3973(19) . ?
C17 C18 1.484(2) . ?
C18 O1 1.2093(17) . ?
C18 O2 1.3288(17) . ?
C19 O2 1.443(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 116.15(13) . . ?
C6 C1 C7 124.08(13) . . ?
C2 C1 C7 119.77(13) . . ?
F1 C2 C3 119.05(15) . . ?
F1 C2 C1 117.23(14) . . ?
C3 C2 C1 123.71(15) . . ?
C4 C3 C2 118.61(16) . . ?
C5 C4 C3 119.74(15) . . ?
C4 C5 C6 120.38(17) . . ?
C1 C6 C5 121.41(15) . . ?
N1 C7 C1 113.79(12) . . ?
O4 C8 N1 120.85(14) . . ?
O4 C8 C9 121.26(15) . . ?
N1 C8 C9 117.89(14) . . ?
N1 C10 C11 116.13(11) . . ?
O3 C11 N2 125.60(14) . . ?
O3 C11 C10 119.75(13) . . ?
N2 C11 C10 114.63(12) . . ?
C13 C12 N2 122.17(13) . . ?
C13 C12 C17 119.06(13) . . ?
N2 C12 C17 118.73(12) . . ?
C14 C13 C12 119.96(16) . . ?
C15 C14 C13 121.11(15) . . ?
C14 C15 C16 119.73(15) . . ?
C15 C16 C17 121.22(16) . . ?
C16 C17 C12 118.91(14) . . ?
C16 C17 C18 119.45(13) . . ?
C12 C17 C18 121.59(12) . . ?
O1 C18 O2 121.38(14) . . ?
O1 C18 C17 125.61(13) . . ?
O2 C18 C17 113.01(12) . . ?
C8 N1 C7 124.38(13) . . ?
C8 N1 C10 118.48(13) . . ?
C7 N1 C10 116.75(12) . . ?
C11 N2 C12 129.83(13) . . ?
C18 O2 C19 116.07(13) . . ?

_refine_diff_density_max         0.365
_refine_diff_density_min         -0.251
_refine_diff_density_rms         0.044

####################################################################### 
# 
# 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_shelx_CCDC4
_database_code_depnum_ccdc_archive 'CCDC 2143853'
loop_
_audit_author_name
_audit_author_address
'Manasa Purushotham'
;Bangalore University 
India
;
_audit_update_record             
;
2022-01-22 deposited with the CCDC.	2022-09-05 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         'C19 H20 N2 O4'
_chemical_formula_sum            'C19 H20 N2 O4'
_chemical_formula_weight         340.37

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

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   8.4482(19)
_cell_length_b                   10.535(3)
_cell_length_c                   10.731(3)
_cell_angle_alpha                101.727(12)
_cell_angle_beta                 97.628(11)
_cell_angle_gamma                104.253(13)
_cell_volume                     889.4(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1614
_cell_measurement_theta_min      5.797
_cell_measurement_theta_max      45.332

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.271
_exptl_crystal_F_000             360
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.090
_shelx_estimated_absorpt_T_min   0.982
_shelx_estimated_absorpt_T_max   0.987
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.982
_exptl_absorpt_correction_T_max  0.987
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker axs kappa apex2 CCD Diffractometer'
_diffrn_measurement_method       'ω and φ scan'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7437
_diffrn_reflns_av_unetI/netI     0.1138
_diffrn_reflns_av_R_equivalents  0.1196
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.478
_diffrn_reflns_theta_max         28.479
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.959
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.959
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.959
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             4317
_reflns_number_gt                2073
_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       'APEX2 (Bruker, 2004)'
_computing_cell_refinement       'APEX2/SAINT (Bruker, 2004)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2004)'
_computing_structure_solution    'SIR92 (Altornare et al., 2014)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
'ORTEP3 (Farrugia, 1997) and Mercury (Bruno et al., 2002)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 2008)'


_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)+(0.0576P)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       0.014(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4317
_refine_ls_number_parameters     229
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1213
_refine_ls_R_factor_gt           0.0611
_refine_ls_wR_factor_ref         0.1678
_refine_ls_wR_factor_gt          0.1398
_refine_ls_goodness_of_fit_ref   0.882
_refine_ls_restrained_S_all      0.882
_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 1.1167(3) 0.8609(3) 0.4353(2) 0.0698(7) Uani 1 1 d . . . . .
H1 H 1.0565 0.8806 0.3663 0.084 Uiso 1 1 calc R U . . .
C2 C 1.2812(3) 0.8691(3) 0.4399(2) 0.0666(7) Uani 1 1 d . . . . .
H2 H 1.3342 0.8948 0.3747 0.080 Uiso 1 1 calc R U . . .
C3 C 1.3664(3) 0.8390(3) 0.5413(3) 0.0665(7) Uani 1 1 d . . . . .
H3 H 1.4785 0.8445 0.5451 0.080 Uiso 1 1 calc R U . . .
C4 C 1.2901(3) 0.8008(2) 0.6380(2) 0.0562(6) Uani 1 1 d . . . . .
H4 H 1.3509 0.7808 0.7065 0.067 Uiso 1 1 calc R U . . .
C5 C 1.1240(2) 0.7918(2) 0.63477(19) 0.0443(5) Uani 1 1 d . . . . .
C6 C 1.0399(3) 0.8235(3) 0.5331(2) 0.0618(7) Uani 1 1 d . . . . .
H6 H 0.9282 0.8197 0.5298 0.074 Uiso 1 1 calc R U . . .
C7 C 1.0434(2) 0.7452(2) 0.7414(2) 0.0530(6) Uani 1 1 d . . . . .
H7A H 1.0484 0.6538 0.7389 0.064 Uiso 1 1 calc R U . . .
H7B H 1.1075 0.8023 0.8244 0.064 Uiso 1 1 calc R U . . .
C8 C 0.7385(3) 0.6443(2) 0.6587(2) 0.0486(5) Uani 1 1 d . . . . .
C9 C 0.7729(3) 0.5213(2) 0.5872(2) 0.0682(7) Uani 1 1 d . . . . .
H9A H 0.7991 0.4693 0.6468 0.102 Uiso 1 1 calc R U . . .
H9B H 0.8655 0.5468 0.5455 0.102 Uiso 1 1 calc R U . . .
H9C H 0.6765 0.4681 0.5230 0.102 Uiso 1 1 calc R U . . .
C10 C 0.8402(3) 0.8704(2) 0.79687(19) 0.0503(5) Uani 1 1 d . . . . .
H10A H 0.7487 0.8844 0.7417 0.060 Uiso 1 1 calc R U . . .
H10B H 0.9377 0.9448 0.8034 0.060 Uiso 1 1 calc R U . . .
C11 C 0.7992(2) 0.8779(2) 0.9304(2) 0.0461(5) Uani 1 1 d . . . . .
C12 C 0.7403(2) 0.7335(2) 1.08516(19) 0.0434(5) Uani 1 1 d . . . . .
C13 C 0.7176(2) 0.6004(2) 1.09852(19) 0.0467(5) Uani 1 1 d . . . . .
C14 C 0.6617(3) 0.5681(3) 1.2080(2) 0.0627(7) Uani 1 1 d . . . . .
H14 H 0.6444 0.4800 1.2171 0.075 Uiso 1 1 calc R U . . .
C15 C 0.6320(3) 0.6626(3) 1.3016(2) 0.0701(8) Uani 1 1 d . . . . .
H15 H 0.5940 0.6394 1.3736 0.084 Uiso 1 1 calc R U . . .
C16 C 0.6589(3) 0.7933(3) 1.2887(2) 0.0661(7) Uani 1 1 d . . . . .
H16 H 0.6417 0.8588 1.3539 0.079 Uiso 1 1 calc R U . . .
C17 C 0.7104(3) 0.8283(2) 1.1819(2) 0.0552(6) Uani 1 1 d . . . . .
H17 H 0.7256 0.9166 1.1741 0.066 Uiso 1 1 calc R U . . .
C18 C 0.7539(3) 0.4973(2) 1.0014(2) 0.0540(6) Uani 1 1 d . . . . .
C19 C 0.7448(4) 0.2687(3) 0.9330(3) 0.0888(9) Uani 1 1 d . . . . .
H19A H 0.6997 0.2707 0.8467 0.133 Uiso 1 1 calc R U . . .
H19B H 0.6926 0.1832 0.9489 0.133 Uiso 1 1 calc R U . . .
H19C H 0.8625 0.2808 0.9419 0.133 Uiso 1 1 calc R U . . .
N1 N 0.8715(2) 0.74767(17) 0.73369(15) 0.0443(4) Uani 1 1 d . . . . .
N2 N 0.7888(2) 0.76414(16) 0.97223(15) 0.0468(4) Uani 1 1 d . . . . .
H2N H 0.8158 0.7013 0.9224 0.056 Uiso 1 1 calc R U . . .
O1 O 0.7144(2) 0.37521(16) 1.02491(16) 0.0717(5) Uani 1 1 d . . . . .
O2 O 0.8137(2) 0.51556(17) 0.90723(16) 0.0738(5) Uani 1 1 d . . . . .
O3 O 0.7799(2) 0.98089(17) 0.99096(17) 0.0751(5) Uani 1 1 d . . . . .
O4 O 0.59903(18) 0.65746(17) 0.65324(16) 0.0684(5) 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 C2 1.365(3) . ?
C1 C6 1.379(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.359(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.369(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.379(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.366(3) . ?
C5 C7 1.511(3) . ?
C6 H6 0.9300 . ?
C7 N1 1.451(2) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 O4 1.215(2) . ?
C8 N1 1.377(3) . ?
C8 C9 1.481(3) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 N1 1.436(3) . ?
C10 C11 1.510(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 O3 1.206(2) . ?
C11 N2 1.349(2) . ?
C12 C17 1.382(3) . ?
C12 N2 1.402(2) . ?
C12 C13 1.408(3) . ?
C13 C14 1.397(3) . ?
C13 C18 1.465(3) . ?
C14 C15 1.359(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.378(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.366(3) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 O2 1.217(2) . ?
C18 O1 1.331(3) . ?
C19 O1 1.434(3) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
N2 H2N 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
C2 C1 C6 119.9(2) . . ?
C2 C1 H1 120.0 . . ?
C6 C1 H1 120.0 . . ?
C3 C2 C1 119.0(2) . . ?
C3 C2 H2 120.5 . . ?
C1 C2 H2 120.5 . . ?
C2 C3 C4 121.2(2) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?
C3 C4 C5 120.6(2) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C6 C5 C4 117.75(19) . . ?
C6 C5 C7 123.39(17) . . ?
C4 C5 C7 118.84(17) . . ?
C5 C6 C1 121.5(2) . . ?
C5 C6 H6 119.2 . . ?
C1 C6 H6 119.2 . . ?
N1 C7 C5 114.48(15) . . ?
N1 C7 H7A 108.6 . . ?
C5 C7 H7A 108.6 . . ?
N1 C7 H7B 108.6 . . ?
C5 C7 H7B 108.6 . . ?
H7A C7 H7B 107.6 . . ?
O4 C8 N1 119.2(2) . . ?
O4 C8 C9 122.8(2) . . ?
N1 C8 C9 118.0(2) . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N1 C10 C11 116.68(16) . . ?
N1 C10 H10A 108.1 . . ?
C11 C10 H10A 108.1 . . ?
N1 C10 H10B 108.1 . . ?
C11 C10 H10B 108.1 . . ?
H10A C10 H10B 107.3 . . ?
O3 C11 N2 125.39(19) . . ?
O3 C11 C10 119.69(18) . . ?
N2 C11 C10 114.92(18) . . ?
C17 C12 N2 122.41(19) . . ?
C17 C12 C13 119.09(18) . . ?
N2 C12 C13 118.48(19) . . ?
C14 C13 C12 118.6(2) . . ?
C14 C13 C18 120.1(2) . . ?
C12 C13 C18 121.32(17) . . ?
C15 C14 C13 121.4(2) . . ?
C15 C14 H14 119.3 . . ?
C13 C14 H14 119.3 . . ?
C14 C15 C16 119.4(2) . . ?
C14 C15 H15 120.3 . . ?
C16 C15 H15 120.3 . . ?
C17 C16 C15 121.0(2) . . ?
C17 C16 H16 119.5 . . ?
C15 C16 H16 119.5 . . ?
C16 C17 C12 120.5(2) . . ?
C16 C17 H17 119.7 . . ?
C12 C17 H17 119.7 . . ?
O2 C18 O1 120.8(2) . . ?
O2 C18 C13 126.02(19) . . ?
O1 C18 C13 113.1(2) . . ?
O1 C19 H19A 109.5 . . ?
O1 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O1 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C8 N1 C10 118.25(17) . . ?
C8 N1 C7 123.64(19) . . ?
C10 N1 C7 117.78(18) . . ?
C11 N2 C12 129.41(18) . . ?
C11 N2 H2N 115.3 . . ?
C12 N2 H2N 115.3 . . ?
C18 O1 C19 116.3(2) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 0.4(4) . . . . ?
C1 C2 C3 C4 0.1(4) . . . . ?
C2 C3 C4 C5 0.0(4) . . . . ?
C3 C4 C5 C6 -0.7(3) . . . . ?
C3 C4 C5 C7 178.2(2) . . . . ?
C4 C5 C6 C1 1.2(4) . . . . ?
C7 C5 C6 C1 -177.6(2) . . . . ?
C2 C1 C6 C5 -1.1(4) . . . . ?
C6 C5 C7 N1 -5.0(3) . . . . ?
C4 C5 C7 N1 176.2(2) . . . . ?
N1 C10 C11 O3 176.32(19) . . . . ?
N1 C10 C11 N2 -3.1(3) . . . . ?
C17 C12 C13 C14 1.5(3) . . . . ?
N2 C12 C13 C14 -177.01(18) . . . . ?
C17 C12 C13 C18 -177.50(19) . . . . ?
N2 C12 C13 C18 3.9(3) . . . . ?
C12 C13 C14 C15 -1.1(3) . . . . ?
C18 C13 C14 C15 177.9(2) . . . . ?
C13 C14 C15 C16 -0.5(4) . . . . ?
C14 C15 C16 C17 1.8(4) . . . . ?
C15 C16 C17 C12 -1.4(3) . . . . ?
N2 C12 C17 C16 178.18(18) . . . . ?
C13 C12 C17 C16 -0.3(3) . . . . ?
C14 C13 C18 O2 -174.7(2) . . . . ?
C12 C13 C18 O2 4.3(4) . . . . ?
C14 C13 C18 O1 5.4(3) . . . . ?
C12 C13 C18 O1 -175.56(17) . . . . ?
O4 C8 N1 C10 -3.4(3) . . . . ?
C9 C8 N1 C10 176.21(17) . . . . ?
O4 C8 N1 C7 -176.57(17) . . . . ?
C9 C8 N1 C7 3.1(3) . . . . ?
C11 C10 N1 C8 89.0(2) . . . . ?
C11 C10 N1 C7 -97.5(2) . . . . ?
C5 C7 N1 C8 84.7(2) . . . . ?
C5 C7 N1 C10 -88.5(2) . . . . ?
O3 C11 N2 C12 6.4(4) . . . . ?
C10 C11 N2 C12 -174.23(18) . . . . ?
C17 C12 N2 C11 -7.1(3) . . . . ?
C13 C12 N2 C11 171.36(19) . . . . ?
O2 C18 O1 C19 -0.6(3) . . . . ?
C13 C18 O1 C19 179.34(19) . . . . ?

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
N2 H2N O2 0.86 1.93 2.638(2) 139.2 .
N2 H2N N1 0.86 2.26 2.725(2) 114.1 .
C7 H7B O3 0.97 2.58 3.489(3) 156.8 2_777
C19 H19B O3 0.96 2.52 3.290(3) 136.9 1_545
C17 H17 O3 0.93 2.27 2.884(3) 122.9 .
C9 H9C O4 0.96 2.65 3.611(3) 174.5 2_666

_refine_diff_density_max         0.218
_refine_diff_density_min         -0.203
_refine_diff_density_rms         0.051

