# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_20160325szzindia_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1533305'
_audit_update_record             
;
2017-02-17 deposited with the CCDC.
2017-03-06 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H12 F3 N O'
_chemical_formula_weight         255.24

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'

_symmetry_cell_setting           Monoclinic'
_symmetry_space_group_name_H-M   P2(1)/c

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

_cell_length_a                   7.8148(8)
_cell_length_b                   10.2559(11)
_cell_length_c                   14.9546(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.525(3)
_cell_angle_gamma                90.00
_cell_volume                     1174.4(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    5467
_cell_measurement_theta_min      2.66
_cell_measurement_theta_max      28.37

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.444
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             528
_exptl_absorpt_coefficient_mu    0.124
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9662
_exptl_absorpt_correction_T_max  0.9733
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7981
_diffrn_reflns_av_R_equivalents  0.0527
_diffrn_reflns_av_sigmaI/netI    0.0449
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.66
_diffrn_reflns_theta_max         25.01
_reflns_number_total             2060
_reflns_number_gt                1823
_reflns_threshold_expression     >2sigma(I)

_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-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0620P)²+0.6000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.096(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2060
_refine_ls_number_parameters     166
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0499
_refine_ls_R_factor_gt           0.0445
_refine_ls_wR_factor_ref         0.1227
_refine_ls_wR_factor_gt          0.1177
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.6648(3) 0.5148(2) 0.19478(12) 0.0320(5) Uani 1 1 d . . .
C2 C 0.8238(2) 0.55493(17) 0.26179(11) 0.0251(4) Uani 1 1 d . . .
H2A H 0.8767 0.6291 0.2376 0.030 Uiso 1 1 calc R . .
H2B H 0.9076 0.4840 0.2697 0.030 Uiso 1 1 calc R . .
C3 C 0.7847(2) 0.59074(16) 0.35338(11) 0.0223(4) Uani 1 1 d . . .
C4 C 0.7400(2) 0.71888(18) 0.36738(13) 0.0302(4) Uani 1 1 d . . .
H4 H 0.7425 0.7796 0.3215 0.036 Uiso 1 1 calc R . .
C5 C 0.6913(3) 0.76055(18) 0.44783(13) 0.0347(5) Uani 1 1 d . . .
H5 H 0.6608 0.8473 0.4539 0.042 Uiso 1 1 calc R . .
C6 C 0.6879(2) 0.67484(19) 0.51778(12) 0.0307(5) Uani 1 1 d . . .
H6 H 0.6547 0.7012 0.5713 0.037 Uiso 1 1 calc R . .
C7 C 0.7365(2) 0.54662(17) 0.50515(11) 0.0238(4) Uani 1 1 d . . .
C8 C 0.7851(2) 0.50022(16) 0.42456(11) 0.0200(4) Uani 1 1 d . . .
C9 C 0.8201(2) 0.36156(16) 0.43970(11) 0.0210(4) Uani 1 1 d . . .
C10 C 0.8822(2) 0.26200(17) 0.38484(11) 0.0244(4) Uani 1 1 d . . .
C11 C 0.8841(3) 0.12267(17) 0.41808(13) 0.0323(5) Uani 1 1 d . . .
H11A H 0.9096 0.0652 0.3718 0.048 Uiso 1 1 calc R . .
H11B H 0.7719 0.1012 0.4310 0.048 Uiso 1 1 calc R . .
H11C H 0.9720 0.1132 0.4726 0.048 Uiso 1 1 calc R . .
C12 C 0.7914(2) 0.33591(17) 0.52621(11) 0.0244(4) Uani 1 1 d . . .
H12 H 0.8034 0.2541 0.5536 0.029 Uiso 1 1 calc R . .
C13 C 0.6999(3) 0.4524(2) 0.65556(12) 0.0357(5) Uani 1 1 d . . .
H13A H 0.5766 0.4665 0.6490 0.054 Uiso 1 1 calc R . .
H13B H 0.7624 0.5235 0.6889 0.054 Uiso 1 1 calc R . .
H13C H 0.7317 0.3724 0.6880 0.054 Uiso 1 1 calc R . .
F1 F 0.58059(16) 0.41407(12) 0.22289(8) 0.0433(4) Uani 1 1 d . . .
F2 F 0.70392(17) 0.47854(14) 0.11436(7) 0.0502(4) Uani 1 1 d . . .
F3 F 0.54589(16) 0.61044(14) 0.17466(8) 0.0500(4) Uani 1 1 d . . .
N1 N 0.74412(18) 0.44425(15) 0.56572(9) 0.0255(4) Uani 1 1 d . . .
O1 O 0.93542(19) 0.28479(13) 0.31462(8) 0.0362(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 F1 1.337(2) . ?
C1 F3 1.343(2) . ?
C1 F2 1.351(2) . ?
C1 C2 1.490(3) . ?
C2 C3 1.507(2) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.387(3) . ?
C3 C8 1.412(2) . ?
C4 C5 1.399(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.371(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.392(3) . ?
C6 H6 0.9300 . ?
C7 N1 1.380(2) . ?
C7 C8 1.416(2) . ?
C8 C9 1.457(2) . ?
C9 C12 1.382(2) . ?
C9 C10 1.453(2) . ?
C10 O1 1.226(2) . ?
C10 C11 1.512(2) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 N1 1.345(2) . ?
C12 H12 0.9300 . ?
C13 N1 1.455(2) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?

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
F1 C1 F3 105.84(16) . . ?
F1 C1 F2 106.31(15) . . ?
F3 C1 F2 105.72(15) . . ?
F1 C1 C2 113.50(15) . . ?
F3 C1 C2 113.28(16) . . ?
F2 C1 C2 111.59(16) . . ?
C1 C2 C3 112.68(14) . . ?
C1 C2 H2A 109.1 . . ?
C3 C2 H2A 109.1 . . ?
C1 C2 H2B 109.1 . . ?
C3 C2 H2B 109.1 . . ?
H2A C2 H2B 107.8 . . ?
C4 C3 C8 118.16(16) . . ?
C4 C3 C2 118.11(15) . . ?
C8 C3 C2 123.70(15) . . ?
C3 C4 C5 122.64(17) . . ?
C3 C4 H4 118.7 . . ?
C5 C4 H4 118.7 . . ?
C6 C5 C4 120.69(17) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C5 C6 C7 117.07(16) . . ?
C5 C6 H6 121.5 . . ?
C7 C6 H6 121.5 . . ?
N1 C7 C6 127.36(16) . . ?
N1 C7 C8 108.61(15) . . ?
C6 C7 C8 124.03(16) . . ?
C3 C8 C7 117.40(15) . . ?
C3 C8 C9 136.94(15) . . ?
C7 C8 C9 105.65(14) . . ?
C12 C9 C10 122.01(15) . . ?
C12 C9 C8 105.70(14) . . ?
C10 C9 C8 132.20(14) . . ?
O1 C10 C9 123.93(16) . . ?
O1 C10 C11 118.61(15) . . ?
C9 C10 C11 117.44(14) . . ?
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 . . ?
N1 C12 C9 111.38(15) . . ?
N1 C12 H12 124.3 . . ?
C9 C12 H12 124.3 . . ?
N1 C13 H13A 109.5 . . ?
N1 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
N1 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 N1 C7 108.65(13) . . ?
C12 N1 C13 126.16(16) . . ?
C7 N1 C13 125.13(16) . . ?

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
F1 C1 C2 C3 -57.6(2) . . . . ?
F3 C1 C2 C3 63.11(19) . . . . ?
F2 C1 C2 C3 -177.72(15) . . . . ?
C1 C2 C3 C4 -88.6(2) . . . . ?
C1 C2 C3 C8 89.0(2) . . . . ?
C8 C3 C4 C5 -1.7(3) . . . . ?
C2 C3 C4 C5 176.09(16) . . . . ?
C3 C4 C5 C6 0.8(3) . . . . ?
C4 C5 C6 C7 0.6(3) . . . . ?
C5 C6 C7 N1 179.59(17) . . . . ?
C5 C6 C7 C8 -1.3(3) . . . . ?
C4 C3 C8 C7 1.0(2) . . . . ?
C2 C3 C8 C7 -176.61(14) . . . . ?
C4 C3 C8 C9 179.32(18) . . . . ?
C2 C3 C8 C9 1.7(3) . . . . ?
N1 C7 C8 C3 179.70(14) . . . . ?
C6 C7 C8 C3 0.4(2) . . . . ?
N1 C7 C8 C9 0.92(17) . . . . ?
C6 C7 C8 C9 -178.36(16) . . . . ?
C3 C8 C9 C12 -178.67(18) . . . . ?
C7 C8 C9 C12 -0.25(17) . . . . ?
C3 C8 C9 C10 4.8(3) . . . . ?
C7 C8 C9 C10 -176.75(17) . . . . ?
C12 C9 C10 O1 -167.98(16) . . . . ?
C8 C9 C10 O1 8.0(3) . . . . ?
C12 C9 C10 C11 10.8(2) . . . . ?
C8 C9 C10 C11 -173.22(17) . . . . ?
C10 C9 C12 N1 176.41(15) . . . . ?
C8 C9 C12 N1 -0.53(18) . . . . ?
C9 C12 N1 C7 1.13(19) . . . . ?
C9 C12 N1 C13 178.45(15) . . . . ?
C6 C7 N1 C12 177.98(16) . . . . ?
C8 C7 N1 C12 -1.27(18) . . . . ?
C6 C7 N1 C13 0.6(3) . . . . ?
C8 C7 N1 C13 -178.63(15) . . . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        25.01
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.229
_refine_diff_density_min         -0.289
_refine_diff_density_rms         0.048
