# Electronic Supplementary Material (ESI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_170634LT
_database_code_depnum_ccdc_archive 'CCDC 1813512'
_audit_update_record             
;
2018-08-10 deposited with the CCDC.
2018-08-15 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H7 F4 N'
_chemical_formula_weight         265.21

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'
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           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                   13.274(3)
_cell_length_b                   14.344(3)
_cell_length_c                   6.1256(12)
_cell_angle_alpha                90
_cell_angle_beta                 101.518(9)
_cell_angle_gamma                90
_cell_volume                     1142.8(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2286
_cell_measurement_theta_min      2.8401
_cell_measurement_theta_max      25.4100

_exptl_crystal_description       Lamellar
_exptl_crystal_colour            Colorless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.541
_exptl_crystal_F_000             536
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.07
_exptl_crystal_size_min          0.02
_exptl_absorpt_coefficient_mu    0.137
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7919
_exptl_absorpt_correction_T_max  0.9485
_exptl_absorpt_process_details   'SADABS V2014/4 (Bruker AXS Inc.)'
_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 8.3333
_diffrn_reflns_number            8087
_diffrn_reflns_av_unetI/netI     0.0374
_diffrn_reflns_av_R_equivalents  0.0315
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -6
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         1.566
_diffrn_reflns_theta_max         26.424
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measured_fraction_theta_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_point_group_measured_fraction_full 0.974
_reflns_number_total             2261
_reflns_number_gt                1629
_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       'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_data_reduction        'SAINT V8.34A (Bruker AXS Inc., 2013)'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/6 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0740P)²+0.2823P] 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         2261
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0735
_refine_ls_R_factor_gt           0.0460
_refine_ls_wR_factor_ref         0.1476
_refine_ls_wR_factor_gt          0.1159
_refine_ls_goodness_of_fit_ref   1.111
_refine_ls_restrained_S_all      1.111
_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
F1 F 1.40975(11) 0.12044(11) 0.0414(3) 0.0458(5) Uani 1 1 d . . . . .
F2 F 0.56248(10) 0.21412(10) 0.7480(3) 0.0402(4) Uani 1 1 d . . . . .
F3 F 0.53688(10) 0.07057(11) 0.6625(3) 0.0412(4) Uani 1 1 d . . . . .
F4 F 0.61616(10) 0.10874(11) 0.9900(2) 0.0393(4) Uani 1 1 d . . . . .
N1 N 0.79669(14) 0.09111(13) 0.4071(3) 0.0261(5) Uani 1 1 d . . . . .
C1 C 1.32199(18) 0.12057(15) 0.1217(4) 0.0281(6) Uani 1 1 d . . . . .
C2 C 1.23570(18) 0.07977(15) -0.0031(4) 0.0274(6) Uani 1 1 d . . . . .
H4 H 1.2376 0.0517 -0.1427 0.033 Uiso 1 1 calc R U . . .
C3 C 1.14632(17) 0.08068(15) 0.0794(4) 0.0233(5) Uani 1 1 d . . . . .
H7 H 1.0858 0.0530 -0.0045 0.028 Uiso 1 1 calc R U . . .
C4 C 1.14364(16) 0.12176(15) 0.2843(4) 0.0211(5) Uani 1 1 d . . . . .
C5 C 1.05144(18) 0.12169(15) 0.3733(4) 0.0243(5) Uani 1 1 d . . . . .
C6 C 0.97480(18) 0.12149(15) 0.4484(4) 0.0245(5) Uani 1 1 d . . . . .
C7 C 0.88323(16) 0.12291(14) 0.5403(4) 0.0212(5) Uani 1 1 d . . . . .
C8 C 0.88502(17) 0.15646(14) 0.7554(4) 0.0219(5) Uani 1 1 d . . . . .
H2 H 0.9475 0.1781 0.8449 0.026 Uiso 1 1 calc R U . . .
C9 C 0.79542(17) 0.15790(15) 0.8360(4) 0.0221(5) Uani 1 1 d . . . . .
H1 H 0.7949 0.1796 0.9823 0.026 Uiso 1 1 calc R U . . .
C10 C 0.70571(16) 0.12673(15) 0.6980(4) 0.0198(5) Uani 1 1 d . . . . .
C11 C 0.60572(17) 0.12970(16) 0.7746(4) 0.0230(5) Uani 1 1 d . . . . .
C12 C 0.71094(18) 0.09363(16) 0.4874(4) 0.0248(5) Uani 1 1 d . . . . .
H3 H 0.6494 0.0714 0.3953 0.030 Uiso 1 1 calc R U . . .
C13 C 1.32301(18) 0.16170(16) 0.3256(4) 0.0281(6) Uani 1 1 d . . . . .
H5 H 1.3840 0.1891 0.4083 0.034 Uiso 1 1 calc R U . . .
C14 C 1.23314(17) 0.16196(15) 0.4065(4) 0.0244(5) Uani 1 1 d . . . . .
H6 H 1.2322 0.1898 0.5468 0.029 Uiso 1 1 calc R U . . .


_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
F1 C1 1.352(3) . ?
F2 C11 1.336(3) . ?
F3 C11 1.332(3) . ?
F4 C11 1.333(3) . ?
N1 C12 1.328(3) . ?
N1 C7 1.349(3) . ?
C1 C2 1.375(3) . ?
C1 C13 1.379(4) . ?
C2 C3 1.379(3) . ?
C2 H4 0.9500 . ?
C3 C4 1.393(3) . ?
C3 H7 0.9500 . ?
C4 C14 1.396(3) . ?
C4 C5 1.436(3) . ?
C5 C6 1.197(3) . ?
C6 C7 1.438(3) . ?
C7 C8 1.398(3) . ?
C8 C9 1.376(3) . ?
C8 H2 0.9500 . ?
C9 C10 1.390(3) . ?
C9 H1 0.9500 . ?
C10 C12 1.389(3) . ?
C10 C11 1.494(3) . ?
C12 H3 0.9500 . ?
C13 C14 1.380(3) . ?
C13 H5 0.9500 . ?
C14 H6 0.9500 . ?

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
C12 N1 C7 117.1(2) . . ?
F1 C1 C2 118.7(2) . . ?
F1 C1 C13 118.5(2) . . ?
C2 C1 C13 122.9(2) . . ?
C1 C2 C3 118.3(2) . . ?
C1 C2 H4 120.9 . . ?
C3 C2 H4 120.9 . . ?
C2 C3 C4 120.8(2) . . ?
C2 C3 H7 119.6 . . ?
C4 C3 H7 119.6 . . ?
C3 C4 C14 119.0(2) . . ?
C3 C4 C5 121.2(2) . . ?
C14 C4 C5 119.7(2) . . ?
C6 C5 C4 179.7(3) . . ?
C5 C6 C7 178.9(2) . . ?
N1 C7 C8 122.6(2) . . ?
N1 C7 C6 116.3(2) . . ?
C8 C7 C6 121.1(2) . . ?
C9 C8 C7 119.4(2) . . ?
C9 C8 H2 120.3 . . ?
C7 C8 H2 120.3 . . ?
C8 C9 C10 118.3(2) . . ?
C8 C9 H1 120.9 . . ?
C10 C9 H1 120.9 . . ?
C12 C10 C9 118.6(2) . . ?
C12 C10 C11 120.9(2) . . ?
C9 C10 C11 120.4(2) . . ?
F3 C11 F4 106.96(18) . . ?
F3 C11 F2 106.28(18) . . ?
F4 C11 F2 106.41(18) . . ?
F3 C11 C10 112.37(18) . . ?
F4 C11 C10 112.41(18) . . ?
F2 C11 C10 111.98(18) . . ?
N1 C12 C10 124.0(2) . . ?
N1 C12 H3 118.0 . . ?
C10 C12 H3 118.0 . . ?
C1 C13 C14 118.2(2) . . ?
C1 C13 H5 120.9 . . ?
C14 C13 H5 120.9 . . ?
C13 C14 C4 120.7(2) . . ?
C13 C14 H6 119.6 . . ?
C4 C14 H6 119.6 . . ?

_refine_diff_density_max         0.271
_refine_diff_density_min         -0.311
_refine_diff_density_rms         0.076

_shelxl_version_number           2014/6

