# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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 2352170'
loop_
_audit_author_name
_audit_author_address
'VENKATACHALAM RAJESHKUMAR'
;National Institute of Technology Warangal
India
;
_audit_update_record             
;
2024-04-30 deposited with the CCDC.	2024-08-20 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         'C14 H13 Cl N2 O3'
_chemical_formula_sum            'C14 H13 Cl N2 O3'
_chemical_formula_weight         292.71

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

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

_cell_length_a                   6.9833(6)
_cell_length_b                   7.9155(7)
_cell_length_c                   24.658(2)
_cell_angle_alpha                90
_cell_angle_beta                 91.509(5)
_cell_angle_gamma                90
_cell_volume                     1362.5(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5384

_cell_measurement_theta_min      5.407
_cell_measurement_theta_max      49.531

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.427
_exptl_crystal_F_000             608
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.289
_shelx_estimated_absorpt_T_min   0.893
_shelx_estimated_absorpt_T_max   0.944
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.893
_exptl_absorpt_correction_T_max  0.944
_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            15969
_diffrn_reflns_av_unetI/netI     0.0308
_diffrn_reflns_av_R_equivalents  0.0364
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         2.703
_diffrn_reflns_theta_max         28.381
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3330
_reflns_number_gt                2353
_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)+(0.0686P)²+0.4748P] 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         3330
_refine_ls_number_parameters     181
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0732
_refine_ls_R_factor_gt           0.0468
_refine_ls_wR_factor_ref         0.1373
_refine_ls_wR_factor_gt          0.1193
_refine_ls_goodness_of_fit_ref   0.990
_refine_ls_restrained_S_all      0.990
_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 0.6111(3) 0.5533(2) 0.39760(7) 0.0429(4) Uani 1 1 d . . . . .
H1 H 0.6614 0.4897 0.3696 0.051 Uiso 1 1 calc R U . . .
C2 C 0.7316(3) 0.6199(3) 0.43744(8) 0.0505(5) Uani 1 1 d . . . . .
H2 H 0.8627 0.5998 0.4368 0.061 Uiso 1 1 calc R U . . .
C3 C 0.6564(3) 0.7157(3) 0.47788(8) 0.0523(5) Uani 1 1 d . . . . .
C4 C 0.4632(4) 0.7463(3) 0.48018(9) 0.0613(6) Uani 1 1 d . . . . .
H4 H 0.4142 0.8124 0.5077 0.074 Uiso 1 1 calc R U . . .
C5 C 0.3437(3) 0.6772(3) 0.44090(9) 0.0543(5) Uani 1 1 d . . . . .
H5 H 0.2124 0.6954 0.4424 0.065 Uiso 1 1 calc R U . . .
C6 C 0.4155(3) 0.5810(2) 0.39918(7) 0.0387(4) Uani 1 1 d . . . . .
C7 C 0.2791(3) 0.5074(2) 0.35857(7) 0.0401(4) Uani 1 1 d . . . . .
C8 C 0.3556(2) 0.4499(2) 0.30544(7) 0.0353(4) Uani 1 1 d . . . . .
C9 C 0.4946(2) 0.4100(2) 0.23314(7) 0.0340(4) Uani 1 1 d . . . . .
C10 C 0.6303(2) 0.4344(2) 0.18809(7) 0.0364(4) Uani 1 1 d . . . . .
H10 H 0.6241 0.3347 0.1646 0.044 Uiso 1 1 calc R U . . .
C11 C 0.5710(3) 0.5887(3) 0.15466(7) 0.0452(5) Uani 1 1 d . . . . .
H11A H 0.4469 0.5685 0.1373 0.054 Uiso 1 1 calc R U . . .
H11B H 0.5595 0.6858 0.1784 0.054 Uiso 1 1 calc R U . . .
C12 C 0.7168(3) 0.6257(3) 0.11200(8) 0.0536(5) Uani 1 1 d . . . . .
H12A H 0.7207 0.5321 0.0867 0.064 Uiso 1 1 calc R U . . .
H12B H 0.6783 0.7260 0.0919 0.064 Uiso 1 1 calc R U . . .
C13 C 0.9651(3) 0.5035(2) 0.16336(10) 0.0545(5) Uani 1 1 d . . . . .
H13A H 1.0936 0.5224 0.1780 0.065 Uiso 1 1 calc R U . . .
H13B H 0.9705 0.4103 0.1379 0.065 Uiso 1 1 calc R U . . .
C14 C 0.8359(2) 0.4563(2) 0.20885(9) 0.0455(5) Uani 1 1 d . . . . .
H14A H 0.8410 0.5437 0.2364 0.055 Uiso 1 1 calc R U . . .
H14B H 0.8804 0.3517 0.2254 0.055 Uiso 1 1 calc R U . . .
N1 N 0.5004(2) 0.50597(17) 0.27985(6) 0.0359(3) Uani 1 1 d . . . . .
N2 N 0.3564(2) 0.3011(2) 0.23067(7) 0.0486(4) Uani 1 1 d . . . . .
O1 O 0.9013(2) 0.65094(17) 0.13547(6) 0.0549(4) Uani 1 1 d . . . . .
O2 O 0.25933(18) 0.32780(18) 0.27962(5) 0.0480(3) Uani 1 1 d . . . . .
O3 O 0.1099(2) 0.4923(2) 0.36607(6) 0.0613(4) Uani 1 1 d . . . . .
Cl1 Cl 0.80874(12) 0.80368(11) 0.52652(3) 0.0900(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 1.381(3) . ?
C1 C6 1.385(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.369(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.373(3) . ?
C3 Cl1 1.729(2) . ?
C4 C5 1.375(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.385(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.483(3) . ?
C7 O3 1.207(2) . ?
C7 C8 1.498(2) . ?
C8 N1 1.285(2) . ?
C8 O2 1.330(2) . ?
C9 N2 1.294(2) . ?
C9 N1 1.379(2) . ?
C9 C10 1.492(2) . ?
C10 C14 1.521(3) . ?
C10 C11 1.525(3) . ?
C10 H10 0.9800 . ?
C11 C12 1.512(3) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 O1 1.412(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 O1 1.421(2) . ?
C13 C14 1.505(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
N2 O2 1.4157(19) . ?

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 120.16(18) . . ?
C2 C1 H1 119.9 . . ?
C6 C1 H1 119.9 . . ?
C3 C2 C1 119.4(2) . . ?
C3 C2 H2 120.3 . . ?
C1 C2 H2 120.3 . . ?
C2 C3 C4 121.6(2) . . ?
C2 C3 Cl1 119.19(18) . . ?
C4 C3 Cl1 119.19(17) . . ?
C5 C4 C3 118.64(19) . . ?
C5 C4 H4 120.7 . . ?
C3 C4 H4 120.7 . . ?
C4 C5 C6 121.2(2) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 H5 119.4 . . ?
C5 C6 C1 118.97(18) . . ?
C5 C6 C7 118.65(17) . . ?
C1 C6 C7 122.36(16) . . ?
O3 C7 C6 123.32(17) . . ?
O3 C7 C8 118.47(17) . . ?
C6 C7 C8 118.21(15) . . ?
N1 C8 O2 114.23(15) . . ?
N1 C8 C7 128.84(16) . . ?
O2 C8 C7 116.89(14) . . ?
N2 C9 N1 114.31(15) . . ?
N2 C9 C10 122.61(16) . . ?
N1 C9 C10 123.03(15) . . ?
C9 C10 C14 112.15(15) . . ?
C9 C10 C11 109.71(14) . . ?
C14 C10 C11 109.37(15) . . ?
C9 C10 H10 108.5 . . ?
C14 C10 H10 108.5 . . ?
C11 C10 H10 108.5 . . ?
C12 C11 C10 110.66(16) . . ?
C12 C11 H11A 109.5 . . ?
C10 C11 H11A 109.5 . . ?
C12 C11 H11B 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 108.1 . . ?
O1 C12 C11 111.47(16) . . ?
O1 C12 H12A 109.3 . . ?
C11 C12 H12A 109.3 . . ?
O1 C12 H12B 109.3 . . ?
C11 C12 H12B 109.3 . . ?
H12A C12 H12B 108.0 . . ?
O1 C13 C14 112.25(15) . . ?
O1 C13 H13A 109.2 . . ?
C14 C13 H13A 109.2 . . ?
O1 C13 H13B 109.2 . . ?
C14 C13 H13B 109.2 . . ?
H13A C13 H13B 107.9 . . ?
C13 C14 C10 110.88(17) . . ?
C13 C14 H14A 109.5 . . ?
C10 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
C10 C14 H14B 109.5 . . ?
H14A C14 H14B 108.1 . . ?
C8 N1 C9 102.32(14) . . ?
C9 N2 O2 103.51(14) . . ?
C12 O1 C13 110.69(16) . . ?
C8 O2 N2 105.62(12) . . ?

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 -1.1(3) . . . . ?
C1 C2 C3 C4 0.6(3) . . . . ?
C1 C2 C3 Cl1 -178.16(15) . . . . ?
C2 C3 C4 C5 0.5(3) . . . . ?
Cl1 C3 C4 C5 179.27(17) . . . . ?
C3 C4 C5 C6 -1.1(3) . . . . ?
C4 C5 C6 C1 0.6(3) . . . . ?
C4 C5 C6 C7 178.98(19) . . . . ?
C2 C1 C6 C5 0.6(3) . . . . ?
C2 C1 C6 C7 -177.79(17) . . . . ?
C5 C6 C7 O3 -17.9(3) . . . . ?
C1 C6 C7 O3 160.42(19) . . . . ?
C5 C6 C7 C8 161.75(17) . . . . ?
C1 C6 C7 C8 -19.9(2) . . . . ?
O3 C7 C8 N1 150.67(19) . . . . ?
C6 C7 C8 N1 -29.0(3) . . . . ?
O3 C7 C8 O2 -27.0(2) . . . . ?
C6 C7 C8 O2 153.35(16) . . . . ?
N2 C9 C10 C14 -138.48(18) . . . . ?
N1 C9 C10 C14 44.3(2) . . . . ?
N2 C9 C10 C11 99.8(2) . . . . ?
N1 C9 C10 C11 -77.4(2) . . . . ?
C9 C10 C11 C12 174.69(16) . . . . ?
C14 C10 C11 C12 51.3(2) . . . . ?
C10 C11 C12 O1 -57.4(2) . . . . ?
O1 C13 C14 C10 55.8(2) . . . . ?
C9 C10 C14 C13 -172.46(15) . . . . ?
C11 C10 C14 C13 -50.5(2) . . . . ?
O2 C8 N1 C9 0.19(19) . . . . ?
C7 C8 N1 C9 -177.48(17) . . . . ?
N2 C9 N1 C8 -0.7(2) . . . . ?
C10 C9 N1 C8 176.72(15) . . . . ?
N1 C9 N2 O2 0.9(2) . . . . ?
C10 C9 N2 O2 -176.56(15) . . . . ?
C11 C12 O1 C13 61.4(2) . . . . ?
C14 C13 O1 C12 -60.9(2) . . . . ?
N1 C8 O2 N2 0.3(2) . . . . ?
C7 C8 O2 N2 178.28(14) . . . . ?
C9 N2 O2 C8 -0.69(18) . . . . ?

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
C2 H2 O3 0.93 2.63 3.368(2) 137.0 1_655
C2 H2 O3 0.93 2.63 3.368(2) 137.0 1_655

_refine_diff_density_max         0.232
_refine_diff_density_min         -0.401
_refine_diff_density_rms         0.059

####################################################################### 
# 
# 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 2352171'
loop_
_audit_author_name
_audit_author_address
'VENKATACHALAM RAJESHKUMAR'
;National Institute of Technology Warangal
India
;
_audit_update_record             
;
2024-04-30 deposited with the CCDC.	2024-08-20 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         'C16 H7 Cl2 F3 N2 O2'
_chemical_formula_sum            'C16 H7 Cl2 F3 N2 O2'
_chemical_formula_weight         387.14

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'
Cl Cl 0.1484 0.1585 '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                   7.6950(5)
_cell_length_b                   13.3275(11)
_cell_length_c                   15.5682(14)
_cell_angle_alpha                90
_cell_angle_beta                 93.638(4)
_cell_angle_gamma                90
_cell_volume                     1593.4(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    4960

_cell_measurement_theta_min      6.069
_cell_measurement_theta_max      55.874

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.614
_exptl_crystal_F_000             776
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.300
_exptl_absorpt_coefficient_mu    0.453
_shelx_estimated_absorpt_T_min   0.805
_shelx_estimated_absorpt_T_max   0.876
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.805
_exptl_absorpt_correction_T_max  0.876
_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            17321
_diffrn_reflns_av_unetI/netI     0.0348
_diffrn_reflns_av_R_equivalents  0.0347
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.622
_diffrn_reflns_theta_max         28.405
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3971
_reflns_number_gt                2286
_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)+(0.0929P)²+0.7942P] 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         3971
_refine_ls_number_parameters     226
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1071
_refine_ls_R_factor_gt           0.0592
_refine_ls_wR_factor_ref         0.1949
_refine_ls_wR_factor_gt          0.1628
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.022
_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 1.4905(4) 0.6299(3) 0.2244(2) 0.0593(8) Uani 1 1 d . . . . .
H1 H 1.5514 0.5735 0.2446 0.071 Uiso 1 1 calc R U . . .
C2 C 1.5705(4) 0.7227(3) 0.22134(19) 0.0571(8) Uani 1 1 d . . . . .
C3 C 1.4835(4) 0.8069(2) 0.19160(19) 0.0545(7) Uani 1 1 d . . . . .
H3 H 1.5400 0.8685 0.1908 0.065 Uiso 1 1 calc R U . . .
C4 C 1.3088(3) 0.7985(2) 0.16263(18) 0.0486(7) Uani 1 1 d . . . . .
C5 C 1.2207(4) 0.8928(2) 0.13324(19) 0.0544(7) Uani 1 1 d . . . . .
C6 C 1.0384(4) 0.8886(2) 0.09219(19) 0.0511(7) Uani 1 1 d . . . . .
C7 C 0.7965(3) 0.8570(2) 0.03059(18) 0.0487(6) Uani 1 1 d . . . . .
C8 C 0.6519(3) 0.7989(2) -0.00963(18) 0.0470(6) Uani 1 1 d . . . . .
C9 C 0.4974(4) 0.8446(2) -0.03903(19) 0.0531(7) Uani 1 1 d . . . . .
H9 H 0.4883 0.9142 -0.0383 0.064 Uiso 1 1 calc R U . . .
C10 C 0.3570(4) 0.7873(2) -0.0694(2) 0.0559(7) Uani 1 1 d . . . . .
H10 H 0.2532 0.8183 -0.0883 0.067 Uiso 1 1 calc R U . . .
C11 C 0.3710(3) 0.6842(2) -0.07162(19) 0.0523(7) Uani 1 1 d . . . . .
C12 C 0.2192(4) 0.6208(3) -0.0991(2) 0.0645(8) Uani 1 1 d . . . . .
C13 C 0.6669(4) 0.6957(2) -0.0146(2) 0.0612(8) Uani 1 1 d . . . . .
H13 H 0.7713 0.6647 0.0032 0.073 Uiso 1 1 calc R U . . .
C14 C 0.5279(4) 0.6389(2) -0.0459(2) 0.0645(8) Uani 1 1 d . . . . .
H14 H 0.5391 0.5695 -0.0497 0.077 Uiso 1 1 calc R U . . .
C15 C 1.3164(4) 0.6242(2) 0.1962(2) 0.0552(7) Uani 1 1 d . . . . .
C16 C 1.2251(4) 0.7061(2) 0.16479(19) 0.0517(7) Uani 1 1 d . . . . .
H16 H 1.1089 0.7000 0.1452 0.062 Uiso 1 1 calc R U . . .
N1 N 0.9560(3) 0.81518(17) 0.05456(16) 0.0517(6) Uani 1 1 d . . . . .
N2 N 0.7831(3) 0.9506(2) 0.0523(2) 0.0665(7) Uani 1 1 d . . . . .
O1 O 0.9465(3) 0.97346(15) 0.09297(16) 0.0670(6) Uani 1 1 d . . . . .
O2 O 1.2868(3) 0.97418(17) 0.14259(17) 0.0784(7) Uani 1 1 d . . . . .
F1 F 0.0959(4) 0.6670(3) -0.1423(3) 0.1609(16) Uani 1 1 d . . . . .
F2 F 0.2569(4) 0.5467(3) -0.1471(3) 0.1597(16) Uani 1 1 d . . . . .
F3 F 0.1445(4) 0.5825(3) -0.03482(19) 0.1415(14) Uani 1 1 d . . . . .
Cl1 Cl 1.78780(10) 0.73234(9) 0.25663(7) 0.0876(4) Uani 1 1 d . . . . .
Cl2 Cl 1.21231(13) 0.50879(7) 0.19858(8) 0.0888(4) 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 1.383(5) . ?
C1 C15 1.385(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.372(4) . ?
C2 Cl1 1.732(3) . ?
C3 C4 1.395(4) . ?
C3 H3 0.9300 . ?
C4 C16 1.390(4) . ?
C4 C5 1.486(4) . ?
C5 O2 1.203(3) . ?
C5 C6 1.505(4) . ?
C6 N1 1.287(4) . ?
C6 O1 1.334(3) . ?
C7 N2 1.298(4) . ?
C7 N1 1.378(3) . ?
C7 C8 1.464(4) . ?
C8 C13 1.383(4) . ?
C8 C9 1.388(4) . ?
C9 C10 1.381(4) . ?
C9 H9 0.9300 . ?
C10 C11 1.379(4) . ?
C10 H10 0.9300 . ?
C11 C14 1.386(4) . ?
C11 C12 1.482(4) . ?
C12 F1 1.284(4) . ?
C12 F2 1.284(4) . ?
C12 F3 1.290(4) . ?
C13 C14 1.374(4) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 C16 1.372(4) . ?
C15 Cl2 1.735(3) . ?
C16 H16 0.9300 . ?
N2 O1 1.405(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 C15 117.5(3) . . ?
C2 C1 H1 121.2 . . ?
C15 C1 H1 121.2 . . ?
C3 C2 C1 122.3(3) . . ?
C3 C2 Cl1 119.1(3) . . ?
C1 C2 Cl1 118.6(2) . . ?
C2 C3 C4 118.9(3) . . ?
C2 C3 H3 120.6 . . ?
C4 C3 H3 120.6 . . ?
C16 C4 C3 120.1(3) . . ?
C16 C4 C5 123.5(2) . . ?
C3 C4 C5 116.3(3) . . ?
O2 C5 C4 123.0(3) . . ?
O2 C5 C6 117.4(3) . . ?
C4 C5 C6 119.6(2) . . ?
N1 C6 O1 113.8(2) . . ?
N1 C6 C5 129.8(3) . . ?
O1 C6 C5 116.4(2) . . ?
N2 C7 N1 113.7(3) . . ?
N2 C7 C8 123.3(2) . . ?
N1 C7 C8 122.8(2) . . ?
C13 C8 C9 119.4(3) . . ?
C13 C8 C7 119.1(2) . . ?
C9 C8 C7 121.4(2) . . ?
C10 C9 C8 120.4(3) . . ?
C10 C9 H9 119.8 . . ?
C8 C9 H9 119.8 . . ?
C11 C10 C9 119.9(3) . . ?
C11 C10 H10 120.1 . . ?
C9 C10 H10 120.1 . . ?
C10 C11 C14 119.7(3) . . ?
C10 C11 C12 120.9(3) . . ?
C14 C11 C12 119.4(3) . . ?
F1 C12 F2 104.5(4) . . ?
F1 C12 F3 104.2(3) . . ?
F2 C12 F3 106.0(4) . . ?
F1 C12 C11 114.8(3) . . ?
F2 C12 C11 113.8(3) . . ?
F3 C12 C11 112.5(3) . . ?
C14 C13 C8 120.2(3) . . ?
C14 C13 H13 119.9 . . ?
C8 C13 H13 119.9 . . ?
C13 C14 C11 120.4(3) . . ?
C13 C14 H14 119.8 . . ?
C11 C14 H14 119.8 . . ?
C16 C15 C1 122.1(3) . . ?
C16 C15 Cl2 119.1(2) . . ?
C1 C15 Cl2 118.7(2) . . ?
C15 C16 C4 119.1(3) . . ?
C15 C16 H16 120.5 . . ?
C4 C16 H16 120.5 . . ?
C6 N1 C7 102.7(2) . . ?
C7 N2 O1 104.0(2) . . ?
C6 O1 N2 105.8(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
C15 C1 C2 C3 -0.1(5) . . . . ?
C15 C1 C2 Cl1 179.7(2) . . . . ?
C1 C2 C3 C4 -0.6(5) . . . . ?
Cl1 C2 C3 C4 179.5(2) . . . . ?
C2 C3 C4 C16 0.5(4) . . . . ?
C2 C3 C4 C5 178.5(3) . . . . ?
C16 C4 C5 O2 169.4(3) . . . . ?
C3 C4 C5 O2 -8.5(5) . . . . ?
C16 C4 C5 C6 -8.6(4) . . . . ?
C3 C4 C5 C6 173.5(3) . . . . ?
O2 C5 C6 N1 159.5(3) . . . . ?
C4 C5 C6 N1 -22.4(5) . . . . ?
O2 C5 C6 O1 -19.4(4) . . . . ?
C4 C5 C6 O1 158.8(3) . . . . ?
N2 C7 C8 C13 -167.0(3) . . . . ?
N1 C7 C8 C13 8.1(4) . . . . ?
N2 C7 C8 C9 9.9(5) . . . . ?
N1 C7 C8 C9 -175.0(3) . . . . ?
C13 C8 C9 C10 2.9(4) . . . . ?
C7 C8 C9 C10 -173.9(3) . . . . ?
C8 C9 C10 C11 -0.9(4) . . . . ?
C9 C10 C11 C14 -2.1(5) . . . . ?
C9 C10 C11 C12 176.4(3) . . . . ?
C10 C11 C12 F1 18.9(5) . . . . ?
C14 C11 C12 F1 -162.7(4) . . . . ?
C10 C11 C12 F2 139.3(4) . . . . ?
C14 C11 C12 F2 -42.2(5) . . . . ?
C10 C11 C12 F3 -100.1(4) . . . . ?
C14 C11 C12 F3 78.4(4) . . . . ?
C9 C8 C13 C14 -2.1(5) . . . . ?
C7 C8 C13 C14 174.8(3) . . . . ?
C8 C13 C14 C11 -0.8(5) . . . . ?
C10 C11 C14 C13 2.9(5) . . . . ?
C12 C11 C14 C13 -175.6(3) . . . . ?
C2 C1 C15 C16 1.1(5) . . . . ?
C2 C1 C15 Cl2 179.7(2) . . . . ?
C1 C15 C16 C4 -1.2(5) . . . . ?
Cl2 C15 C16 C4 -179.8(2) . . . . ?
C3 C4 C16 C15 0.4(4) . . . . ?
C5 C4 C16 C15 -177.5(3) . . . . ?
O1 C6 N1 C7 -1.0(3) . . . . ?
C5 C6 N1 C7 -179.9(3) . . . . ?
N2 C7 N1 C6 0.1(3) . . . . ?
C8 C7 N1 C6 -175.4(3) . . . . ?
N1 C7 N2 O1 0.7(3) . . . . ?
C8 C7 N2 O1 176.2(3) . . . . ?
N1 C6 O1 N2 1.5(4) . . . . ?
C5 C6 O1 N2 -179.5(2) . . . . ?
C7 N2 O1 C6 -1.2(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
C16 H16 N1 0.93 2.35 2.982(3) 125.0 .
C1 H1 O2 0.93 2.47 3.329(4) 153.4 2_845

_refine_diff_density_max         0.683
_refine_diff_density_min         -0.406
_refine_diff_density_rms         0.060

