# Electronic Supplementary Material (ESI) for Physical Chemistry Chemical Physics.
# This journal is © the Owner Societies 2021

####################################################################### 
# 
# 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_KA1023_0m
_database_code_depnum_ccdc_archive 'CCDC 2063187'
loop_
_audit_author_name
_audit_author_address
'Sridhar Balasubramanian'
;CSIR Indian Institute of Chemical Technology
India
;
_audit_update_record             
;
2021-02-16 deposited with the CCDC.	2021-03-23 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         'C12 H10 F3 N3 O4'
_chemical_formula_sum            'C12 H10 F3 N3 O4'
_chemical_formula_weight         317.23

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                   7.5763(8)
_cell_length_b                   8.5961(9)
_cell_length_c                   10.7211(10)
_cell_angle_alpha                100.721(3)
_cell_angle_beta                 99.964(3)
_cell_angle_gamma                91.329(4)
_cell_volume                     674.59(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9975
_cell_measurement_theta_min      2.73
_cell_measurement_theta_max      30.56

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.562
_exptl_crystal_F_000             324
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.145
_shelx_estimated_absorpt_T_min   0.966
_shelx_estimated_absorpt_T_max   0.989
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5134
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   'SADABS, Bruker, 2016'


_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON-100'
_diffrn_measurement_method       'ω and φ'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16594
_diffrn_reflns_av_unetI/netI     0.0519
_diffrn_reflns_av_R_equivalents  0.0561
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.415
_diffrn_reflns_theta_max         30.566
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4137
_reflns_number_gt                3505
_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       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL2014 (Sheldrick, 2015)'
_computing_molecular_graphics    'DIAMOND (Brandenburg & Putz, 2005)'
_computing_publication_material  'Bruker SHELXTL'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0514P)²+0.2562P] 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         4137
_refine_ls_number_parameters     205
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0520
_refine_ls_R_factor_gt           0.0425
_refine_ls_wR_factor_ref         0.1163
_refine_ls_wR_factor_gt          0.1098
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_restrained_S_all      1.068
_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 0.24190(13) 0.54677(13) 0.65784(10) 0.0104(2) Uani 1 1 d . . . . .
C2 C 0.25439(14) 0.64958(13) 0.57311(11) 0.0128(2) Uani 1 1 d . . . . .
H2 H 0.257431 0.761094 0.602409 0.015 Uiso 1 1 calc R U . . .
C3 C 0.26235(14) 0.58682(13) 0.44501(11) 0.0131(2) Uani 1 1 d . . . . .
H3 H 0.273360 0.655659 0.386622 0.016 Uiso 1 1 calc R U . . .
C4 C 0.25425(13) 0.42416(13) 0.40258(10) 0.0112(2) Uani 1 1 d . . . . .
C5 C 0.24066(13) 0.31926(13) 0.48651(10) 0.0111(2) Uani 1 1 d . . . . .
C6 C 0.23647(14) 0.38278(13) 0.61491(10) 0.0113(2) Uani 1 1 d . . . . .
H6 H 0.229857 0.314035 0.674028 0.014 Uiso 1 1 calc R U . . .
C7 C 0.23914(16) 0.14069(14) 0.44794(11) 0.0157(2) Uani 1 1 d . . . . .
C8 C 0.14329(14) 0.53558(13) 0.86761(10) 0.0106(2) Uani 1 1 d . . . . .
C9 C 0.30798(14) 0.75690(13) 1.00115(10) 0.0112(2) Uani 1 1 d . . . . .
C10 C 0.33611(14) 0.74607(12) 0.86232(10) 0.0110(2) Uani 1 1 d . . . . .
C11 C 0.48798(15) 0.74934(14) 1.09002(12) 0.0171(2) Uani 1 1 d . . . . .
H11A H 0.467121 0.744830 1.177004 0.026 Uiso 1 1 calc R U . . .
H11B H 0.564666 0.843951 1.093347 0.026 Uiso 1 1 calc R U . . .
H11C H 0.547241 0.654394 1.056516 0.026 Uiso 1 1 calc R U . . .
C12 C 0.21328(16) 0.90746(14) 1.04391(12) 0.0180(2) Uani 1 1 d . . . . .
H12A H 0.104472 0.912190 0.980573 0.027 Uiso 1 1 calc R U . . .
H12B H 0.293849 1.000558 1.050248 0.027 Uiso 1 1 calc R U . . .
H12C H 0.180792 0.906177 1.128322 0.027 Uiso 1 1 calc R U . . .
F1 F 0.35668(10) 0.09438(9) 0.37054(7) 0.02035(17) Uani 1 1 d . . . . .
F2 F 0.07740(11) 0.07492(9) 0.38753(8) 0.02534(19) Uani 1 1 d . . . . .
F3 F 0.28403(12) 0.07429(9) 0.55227(7) 0.02620(19) Uani 1 1 d . . . . .
O1 O 0.34960(12) 0.44487(11) 0.21301(8) 0.01895(19) Uani 1 1 d . . . . .
O2 O 0.15117(12) 0.25542(11) 0.20720(8) 0.02001(19) Uani 1 1 d . . . . .
O3 O 0.03540(10) 0.42141(9) 0.82576(8) 0.01345(17) Uani 1 1 d . . . . .
O4 O 0.42359(12) 0.83789(10) 0.82200(8) 0.01718(18) Uani 1 1 d . . . . .
N1 N 0.25298(13) 0.36944(12) 0.26399(9) 0.01354(19) Uani 1 1 d . . . . .
N2 N 0.24122(12) 0.60772(11) 0.78963(9) 0.01067(18) Uani 1 1 d . . . . .
N3 N 0.19009(12) 0.61620(11) 0.98879(9) 0.01246(19) Uani 1 1 d . . . . .
H3N H 0.132(2) 0.601(2) 1.0517(17) 0.021(4) 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 1.3927(15) . ?
C1 C6 1.3965(15) . ?
C1 N2 1.4135(13) . ?
C2 C3 1.3912(15) . ?
C2 H2 0.9500 . ?
C3 C4 1.3840(15) . ?
C3 H3 0.9500 . ?
C4 C5 1.4011(15) . ?
C4 N1 1.4709(14) . ?
C5 C6 1.3894(15) . ?
C5 C7 1.5129(15) . ?
C6 H6 0.9500 . ?
C7 F1 1.3377(13) . ?
C7 F2 1.3407(14) . ?
C7 F3 1.3444(14) . ?
C8 O3 1.2266(13) . ?
C8 N3 1.3372(14) . ?
C8 N2 1.4213(13) . ?
C9 N3 1.4586(14) . ?
C9 C10 1.5260(15) . ?
C9 C12 1.5285(16) . ?
C9 C11 1.5327(15) . ?
C10 O4 1.2045(13) . ?
C10 N2 1.4001(13) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
O1 N1 1.2261(13) . ?
O2 N1 1.2275(13) . ?
N3 H3N 0.894(17) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C6 120.57(10) . . ?
C2 C1 N2 120.18(10) . . ?
C6 C1 N2 119.21(10) . . ?
C3 C2 C1 119.13(10) . . ?
C3 C2 H2 120.4 . . ?
C1 C2 H2 120.4 . . ?
C4 C3 C2 120.04(10) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C4 C5 121.47(10) . . ?
C3 C4 N1 115.94(10) . . ?
C5 C4 N1 122.54(10) . . ?
C6 C5 C4 118.17(10) . . ?
C6 C5 C7 117.56(10) . . ?
C4 C5 C7 124.20(10) . . ?
C5 C6 C1 120.60(10) . . ?
C5 C6 H6 119.7 . . ?
C1 C6 H6 119.7 . . ?
F1 C7 F2 107.51(9) . . ?
F1 C7 F3 106.54(10) . . ?
F2 C7 F3 106.31(10) . . ?
F1 C7 C5 112.36(9) . . ?
F2 C7 C5 112.88(10) . . ?
F3 C7 C5 110.84(9) . . ?
O3 C8 N3 128.69(10) . . ?
O3 C8 N2 123.92(10) . . ?
N3 C8 N2 107.38(9) . . ?
N3 C9 C10 101.37(8) . . ?
N3 C9 C12 110.73(9) . . ?
C10 C9 C12 110.04(9) . . ?
N3 C9 C11 112.00(9) . . ?
C10 C9 C11 110.09(9) . . ?
C12 C9 C11 112.11(9) . . ?
O4 C10 N2 126.05(10) . . ?
O4 C10 C9 127.01(9) . . ?
N2 C10 C9 106.94(9) . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C9 C12 H12A 109.5 . . ?
C9 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C9 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O1 N1 O2 124.90(10) . . ?
O1 N1 C4 117.29(9) . . ?
O2 N1 C4 117.76(9) . . ?
C10 N2 C1 125.47(9) . . ?
C10 N2 C8 110.21(9) . . ?
C1 N2 C8 124.32(9) . . ?
C8 N3 C9 113.72(9) . . ?
C8 N3 H3N 122.4(11) . . ?
C9 N3 H3N 121.9(11) . . ?

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 -0.33(16) . . . . ?
N2 C1 C2 C3 177.34(9) . . . . ?
C1 C2 C3 C4 1.28(16) . . . . ?
C2 C3 C4 C5 -0.94(16) . . . . ?
C2 C3 C4 N1 176.53(9) . . . . ?
C3 C4 C5 C6 -0.37(15) . . . . ?
N1 C4 C5 C6 -177.67(9) . . . . ?
C3 C4 C5 C7 -177.30(10) . . . . ?
N1 C4 C5 C7 5.39(16) . . . . ?
C4 C5 C6 C1 1.32(15) . . . . ?
C7 C5 C6 C1 178.47(9) . . . . ?
C2 C1 C6 C5 -0.99(15) . . . . ?
N2 C1 C6 C5 -178.69(9) . . . . ?
C6 C5 C7 F1 -136.36(10) . . . . ?
C4 C5 C7 F1 40.59(15) . . . . ?
C6 C5 C7 F2 101.85(11) . . . . ?
C4 C5 C7 F2 -81.20(13) . . . . ?
C6 C5 C7 F3 -17.28(14) . . . . ?
C4 C5 C7 F3 159.67(10) . . . . ?
N3 C9 C10 O4 179.10(11) . . . . ?
C12 C9 C10 O4 61.87(14) . . . . ?
C11 C9 C10 O4 -62.18(15) . . . . ?
N3 C9 C10 N2 -1.20(11) . . . . ?
C12 C9 C10 N2 -118.44(9) . . . . ?
C11 C9 C10 N2 117.51(10) . . . . ?
C3 C4 N1 O1 39.00(13) . . . . ?
C5 C4 N1 O1 -143.56(10) . . . . ?
C3 C4 N1 O2 -138.58(10) . . . . ?
C5 C4 N1 O2 38.87(14) . . . . ?
O4 C10 N2 C1 4.49(18) . . . . ?
C9 C10 N2 C1 -175.20(10) . . . . ?
O4 C10 N2 C8 -175.73(11) . . . . ?
C9 C10 N2 C8 4.58(12) . . . . ?
C2 C1 N2 C10 -34.19(15) . . . . ?
C6 C1 N2 C10 143.52(10) . . . . ?
C2 C1 N2 C8 146.06(10) . . . . ?
C6 C1 N2 C8 -36.23(15) . . . . ?
O3 C8 N2 C10 172.81(10) . . . . ?
N3 C8 N2 C10 -6.37(12) . . . . ?
O3 C8 N2 C1 -7.41(17) . . . . ?
N3 C8 N2 C1 173.41(10) . . . . ?
O3 C8 N3 C9 -173.45(11) . . . . ?
N2 C8 N3 C9 5.68(13) . . . . ?
C10 C9 N3 C8 -2.82(12) . . . . ?
C12 C9 N3 C8 113.91(11) . . . . ?
C11 C9 N3 C8 -120.15(11) . . . . ?

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
_geom_hbond_publ_flag
N3 H3N O3 0.894(17) 2.008(17) 2.8923(12) 170.1(16) 2_567 yes
C12 H12B O4 0.98 2.55 3.4072(15) 145.4 2_677 yes

_refine_diff_density_max         0.405
_refine_diff_density_min         -0.462
_refine_diff_density_rms         0.082



####################################################################### 
# 
# 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_KA1024_0m
_database_code_depnum_ccdc_archive 'CCDC 2063188'
loop_
_audit_author_name
_audit_author_address
'Sridhar Balasubramanian'
;CSIR Indian Institute of Chemical Technology
India
;
_audit_update_record             
;
2021-02-16 deposited with the CCDC.	2021-03-23 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         'C12 H10 F3 N3 O4'
_chemical_formula_sum            'C12 H10 F3 N3 O4'
_chemical_formula_weight         317.23

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      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_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+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   11.1754(5)
_cell_length_b                   10.0868(4)
_cell_length_c                   23.6466(10)
_cell_angle_alpha                90
_cell_angle_beta                 101.8274(19)
_cell_angle_gamma                90
_cell_volume                     2608.95(19)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9965
_cell_measurement_theta_min      2.75
_cell_measurement_theta_max      30.53

_exptl_crystal_description       plate
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.615
_exptl_crystal_F_000             1296
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.360
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.149
_shelx_estimated_absorpt_T_min   0.948
_shelx_estimated_absorpt_T_max   0.978
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6586
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   'SADABS, Bruker, 2016'


_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON-100'
_diffrn_measurement_method       'ω and φ'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17180
_diffrn_reflns_av_unetI/netI     0.0253
_diffrn_reflns_av_R_equivalents  0.0234
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       33
_diffrn_reflns_theta_min         2.747
_diffrn_reflns_theta_max         30.576
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3995
_reflns_number_gt                3421
_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       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL2014 (Sheldrick, 2015)'
_computing_molecular_graphics    'DIAMOND (Brandenburg & Putz, 2005)'
_computing_publication_material  'Bruker SHELXTL'

_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+2.3072P] 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         3995
_refine_ls_number_parameters     205
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0457
_refine_ls_R_factor_gt           0.0371
_refine_ls_wR_factor_ref         0.0976
_refine_ls_wR_factor_gt          0.0924
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_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 0.52932(9) 0.34794(10) 0.43620(4) 0.01151(18) Uani 1 1 d . . . . .
C2 C 0.60389(9) 0.45981(11) 0.44518(4) 0.01340(19) Uani 1 1 d . . . . .
H2 H 0.602993 0.521804 0.414851 0.016 Uiso 1 1 calc R U . . .
C3 C 0.67972(9) 0.47989(11) 0.49900(4) 0.01397(19) Uani 1 1 d . . . . .
H3 H 0.733562 0.553751 0.505268 0.017 Uiso 1 1 calc R U . . .
C4 C 0.67603(9) 0.39121(11) 0.54339(4) 0.01205(19) Uani 1 1 d . . . . .
C5 C 0.60135(9) 0.27965(10) 0.53528(4) 0.01165(18) Uani 1 1 d . . . . .
C6 C 0.52958(9) 0.25691(10) 0.48092(4) 0.01212(18) Uani 1 1 d . . . . .
H6 H 0.480503 0.179369 0.474035 0.015 Uiso 1 1 calc R U . . .
C7 C 0.59458(10) 0.18042(11) 0.58211(4) 0.0151(2) Uani 1 1 d . . . . .
C8 C 0.47635(9) 0.36444(11) 0.32780(4) 0.01318(19) Uani 1 1 d . . . . .
C9 C 0.29597(9) 0.23940(11) 0.30824(4) 0.01384(19) Uani 1 1 d . . . . .
C10 C 0.33946(9) 0.25678(11) 0.37340(4) 0.01334(19) Uani 1 1 d . . . . .
C11 C 0.31479(11) 0.09415(12) 0.29334(5) 0.0204(2) Uani 1 1 d . . . . .
H11A H 0.292850 0.082187 0.251354 0.031 Uiso 1 1 calc R U . . .
H11B H 0.262870 0.037463 0.311884 0.031 Uiso 1 1 calc R U . . .
H11C H 0.400702 0.069867 0.307229 0.031 Uiso 1 1 calc R U . . .
C12 C 0.16334(10) 0.28162(13) 0.28783(5) 0.0197(2) Uani 1 1 d . . . . .
H12A H 0.153030 0.372704 0.300444 0.030 Uiso 1 1 calc R U . . .
H12B H 0.110132 0.222197 0.304333 0.030 Uiso 1 1 calc R U . . .
H12C H 0.141495 0.277153 0.245563 0.030 Uiso 1 1 calc R U . . .
F1 F 0.70206(6) 0.16399(8) 0.61861(3) 0.02210(16) Uani 1 1 d . . . . .
F2 F 0.56119(7) 0.06079(7) 0.55963(3) 0.02495(17) Uani 1 1 d . . . . .
F3 F 0.51299(7) 0.21513(8) 0.61350(3) 0.02469(17) Uani 1 1 d . . . . .
O1 O 0.86017(8) 0.44402(10) 0.60344(4) 0.0270(2) Uani 1 1 d . . . . .
O2 O 0.69977(8) 0.42740(10) 0.64136(3) 0.02368(19) Uani 1 1 d . . . . .
O3 O 0.56814(7) 0.42348(9) 0.32205(3) 0.01779(17) Uani 1 1 d . . . . .
O4 O 0.28831(7) 0.21917(9) 0.41069(3) 0.01924(18) Uani 1 1 d . . . . .
N1 N 0.75163(9) 0.42229(10) 0.60045(4) 0.01571(18) Uani 1 1 d . . . . .
N2 N 0.45191(8) 0.32233(9) 0.38189(4) 0.01230(17) Uani 1 1 d . . . . .
N3 N 0.38187(8) 0.32497(10) 0.28682(4) 0.01472(18) Uani 1 1 d . . . . .
H3N H 0.3780(15) 0.3442(17) 0.2502(7) 0.027(4) 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 1.3929(15) . ?
C1 C6 1.4002(14) . ?
C1 N2 1.4173(12) . ?
C2 C3 1.3918(14) . ?
C2 H2 0.9500 . ?
C3 C4 1.3861(14) . ?
C3 H3 0.9500 . ?
C4 C5 1.3907(15) . ?
C4 N1 1.4715(13) . ?
C5 C6 1.3877(13) . ?
C5 C7 1.5059(14) . ?
C6 H6 0.9500 . ?
C7 F3 1.3351(12) . ?
C7 F1 1.3380(12) . ?
C7 F2 1.3404(13) . ?
C8 O3 1.2177(13) . ?
C8 N3 1.3391(13) . ?
C8 N2 1.4261(12) . ?
C9 N3 1.4569(13) . ?
C9 C12 1.5225(15) . ?
C9 C10 1.5277(14) . ?
C9 C11 1.5314(16) . ?
C10 O4 1.2061(13) . ?
C10 N2 1.3976(13) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
O1 N1 1.2203(13) . ?
O2 N1 1.2264(12) . ?
N3 H3N 0.880(16) . ?

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 120.50(9) . . ?
C2 C1 N2 121.38(9) . . ?
C6 C1 N2 118.12(9) . . ?
C3 C2 C1 119.37(9) . . ?
C3 C2 H2 120.3 . . ?
C1 C2 H2 120.3 . . ?
C4 C3 C2 119.44(10) . . ?
C4 C3 H3 120.3 . . ?
C2 C3 H3 120.3 . . ?
C3 C4 C5 121.87(9) . . ?
C3 C4 N1 117.15(9) . . ?
C5 C4 N1 120.95(9) . . ?
C6 C5 C4 118.56(9) . . ?
C6 C5 C7 117.69(9) . . ?
C4 C5 C7 123.75(9) . . ?
C5 C6 C1 120.18(10) . . ?
C5 C6 H6 119.9 . . ?
C1 C6 H6 119.9 . . ?
F3 C7 F1 107.39(8) . . ?
F3 C7 F2 106.87(9) . . ?
F1 C7 F2 106.53(9) . . ?
F3 C7 C5 112.17(9) . . ?
F1 C7 C5 112.52(9) . . ?
F2 C7 C5 111.02(8) . . ?
O3 C8 N3 128.45(9) . . ?
O3 C8 N2 124.51(9) . . ?
N3 C8 N2 107.04(9) . . ?
N3 C9 C12 113.08(9) . . ?
N3 C9 C10 100.75(8) . . ?
C12 C9 C10 112.05(9) . . ?
N3 C9 C11 110.82(9) . . ?
C12 C9 C11 111.43(9) . . ?
C10 C9 C11 108.16(9) . . ?
O4 C10 N2 126.21(9) . . ?
O4 C10 C9 126.92(9) . . ?
N2 C10 C9 106.86(8) . . ?
C9 C11 H11A 109.5 . . ?
C9 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C9 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C9 C12 H12A 109.5 . . ?
C9 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C9 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O1 N1 O2 124.86(9) . . ?
O1 N1 C4 117.92(9) . . ?
O2 N1 C4 117.19(9) . . ?
C10 N2 C1 125.47(8) . . ?
C10 N2 C8 110.12(8) . . ?
C1 N2 C8 124.38(9) . . ?
C8 N3 C9 113.73(8) . . ?
C8 N3 H3N 121.2(11) . . ?
C9 N3 H3N 124.8(11) . . ?

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 0.55(15) . . . . ?
N2 C1 C2 C3 -179.08(9) . . . . ?
C1 C2 C3 C4 -2.65(15) . . . . ?
C2 C3 C4 C5 2.15(15) . . . . ?
C2 C3 C4 N1 -175.78(9) . . . . ?
C3 C4 C5 C6 0.51(15) . . . . ?
N1 C4 C5 C6 178.36(9) . . . . ?
C3 C4 C5 C7 179.80(10) . . . . ?
N1 C4 C5 C7 -2.35(15) . . . . ?
C4 C5 C6 C1 -2.63(15) . . . . ?
C7 C5 C6 C1 178.03(9) . . . . ?
C2 C1 C6 C5 2.13(15) . . . . ?
N2 C1 C6 C5 -178.23(9) . . . . ?
C6 C5 C7 F3 -93.65(11) . . . . ?
C4 C5 C7 F3 87.05(12) . . . . ?
C6 C5 C7 F1 145.13(9) . . . . ?
C4 C5 C7 F1 -34.17(14) . . . . ?
C6 C5 C7 F2 25.85(13) . . . . ?
C4 C5 C7 F2 -153.45(10) . . . . ?
N3 C9 C10 O4 169.90(11) . . . . ?
C12 C9 C10 O4 49.40(16) . . . . ?
C11 C9 C10 O4 -73.81(14) . . . . ?
N3 C9 C10 N2 -11.42(11) . . . . ?
C12 C9 C10 N2 -131.91(10) . . . . ?
C11 C9 C10 N2 104.87(10) . . . . ?
C3 C4 N1 O1 -53.35(14) . . . . ?
C5 C4 N1 O1 128.70(11) . . . . ?
C3 C4 N1 O2 124.99(11) . . . . ?
C5 C4 N1 O2 -52.96(14) . . . . ?
O4 C10 N2 C1 4.56(18) . . . . ?
C9 C10 N2 C1 -174.13(9) . . . . ?
O4 C10 N2 C8 -173.43(11) . . . . ?
C9 C10 N2 C8 7.87(12) . . . . ?
C2 C1 N2 C10 -148.88(10) . . . . ?
C6 C1 N2 C10 31.48(15) . . . . ?
C2 C1 N2 C8 28.84(15) . . . . ?
C6 C1 N2 C8 -150.80(10) . . . . ?
O3 C8 N2 C10 -179.61(11) . . . . ?
N3 C8 N2 C10 -0.49(12) . . . . ?
O3 C8 N2 C1 2.37(17) . . . . ?
N3 C8 N2 C1 -178.51(9) . . . . ?
O3 C8 N3 C9 171.26(11) . . . . ?
N2 C8 N3 C9 -7.81(13) . . . . ?
C12 C9 N3 C8 131.72(10) . . . . ?
C10 C9 N3 C8 11.97(12) . . . . ?
C11 C9 N3 C8 -102.34(11) . . . . ?

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
_geom_hbond_publ_flag
N3 H3N O3 0.880(16) 2.083(17) 2.9183(11) 158.1(15) 2_655 yes
C11 H11A O2 0.98 2.60 3.5666(14) 169.9 8_455 yes
C11 H11B O3 0.98 2.52 3.4337(14) 155.9 3_445 yes

_refine_diff_density_max         0.427
_refine_diff_density_min         -0.307
_refine_diff_density_rms         0.063



