# 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_1
_database_code_depnum_ccdc_archive 'CCDC 1572973'
_audit_update_record             
;
2017-09-06 deposited with the CCDC.
2017-10-04 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         ?
_chemical_formula_sum            'C H F N O'
_chemical_formula_weight         62.03

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           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                   4.4593(5)
_cell_length_b                   15.9030(18)
_cell_length_c                   16.534(2)
_cell_angle_alpha                90
_cell_angle_beta                 91.298(2)
_cell_angle_gamma                90
_cell_volume                     1172.2(2)
_cell_formula_units_Z            23
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    2.021
_exptl_crystal_F_000             713
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.227
_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  ?
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7389
_diffrn_reflns_av_unetI/netI     0.0279
_diffrn_reflns_av_R_equivalents  0.0218
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.777
_diffrn_reflns_theta_max         28.390
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2887
_reflns_number_gt                2241
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.1000P)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     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2887
_refine_ls_number_parameters     164
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0519
_refine_ls_R_factor_gt           0.0394
_refine_ls_wR_factor_ref         0.1494
_refine_ls_wR_factor_gt          0.1348
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_restrained_S_all      1.070
_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
F1 F 0.00353(18) 0.28375(5) 0.61623(5) 0.0611(3) Uani 1 1 d . . . . .
N2 N 0.6591(2) 0.20722(6) 0.83706(6) 0.0407(3) Uani 1 1 d . . . . .
C11 C 0.9446(2) 0.31941(8) 0.90134(7) 0.0392(3) Uani 1 1 d . . . . .
C5 C 0.5351(2) 0.26515(7) 0.78273(7) 0.0365(3) Uani 1 1 d . . . . .
N1 N 0.8416(2) 0.37470(6) 0.84961(6) 0.0398(3) Uani 1 1 d . . . . .
O1 O 0.9598(2) 0.45714(5) 1.16610(5) 0.0487(3) Uani 1 1 d . . . . .
H1 H 0.9934 0.5078 1.1666 0.073 Uiso 1 1 calc R U . . .
C6 C 0.3217(3) 0.24256(8) 0.72354(7) 0.0421(3) Uani 1 1 d . . . . .
H6 H 0.2551 0.1874 0.7185 0.051 Uiso 1 1 calc R U . . .
C3 C 0.5146(3) 0.40885(8) 0.73692(8) 0.0441(3) Uani 1 1 d . . . . .
H3 H 0.5785 0.4644 0.7411 0.053 Uiso 1 1 calc R U . . .
C4 C 0.6326(2) 0.34886(7) 0.79031(7) 0.0368(3) Uani 1 1 d . . . . .
C10 C 0.8590(3) 0.23307(8) 0.89872(7) 0.0415(3) Uani 1 1 d . . . . .
C2 C 0.3053(3) 0.38734(8) 0.67812(8) 0.0471(3) Uani 1 1 d . . . . .
H2 H 0.2272 0.4275 0.6426 0.056 Uiso 1 1 calc R U . . .
C13 C 0.9615(3) 0.38709(8) 1.03682(7) 0.0402(3) Uani 1 1 d . . . . .
H13A H 0.8442 0.4338 1.0154 0.048 Uiso 1 1 calc R U . . .
H13B H 0.8225 0.3445 1.0549 0.048 Uiso 1 1 calc R U . . .
C1 C 0.2142(3) 0.30431(8) 0.67333(7) 0.0436(3) Uani 1 1 d . . . . .
C14 C 1.1461(3) 0.41747(8) 1.10862(7) 0.0417(3) Uani 1 1 d . . . . .
H14A H 1.2492 0.3702 1.1338 0.050 Uiso 1 1 calc R U . . .
H14B H 1.2962 0.4570 1.0906 0.050 Uiso 1 1 calc R U . . .
C12 C 1.1483(3) 0.35035(9) 0.96882(8) 0.0451(3) Uani 1 1 d . . . . .
H12A H 1.2821 0.3931 0.9484 0.054 Uiso 1 1 calc R U . . .
H12B H 1.2694 0.3042 0.9896 0.054 Uiso 1 1 calc R U . . .
C9 C 0.9356(4) 0.16292(9) 0.94334(9) 0.0562(4) Uani 1 1 d . . . . .
H9 H 1.0645 0.1613 0.9883 0.067 Uiso 1 1 calc R U . . .
C7 C 0.6163(4) 0.12222(8) 0.84361(9) 0.0557(4) Uani 1 1 d . . . . .
H7 H 0.4949 0.0893 0.8099 0.067 Uiso 1 1 calc R U . . .
C8 C 0.7836(4) 0.09445(10) 0.90850(10) 0.0662(4) Uani 1 1 d . . . . .
H8 H 0.7948 0.0391 0.9266 0.079 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 1.3567(13) . ?
N2 C7 1.3697(17) . ?
N2 C5 1.3925(15) . ?
N2 C10 1.4005(14) . ?
C11 N1 1.3031(16) . ?
C11 C10 1.4255(18) . ?
C11 C12 1.5055(15) . ?
C5 C6 1.3965(16) . ?
C5 C4 1.4052(16) . ?
N1 C4 1.3989(14) . ?
O1 C14 1.4240(15) . ?
C6 C1 1.3658(18) . ?
C3 C2 1.3756(17) . ?
C3 C4 1.3948(17) . ?
C10 C9 1.3762(19) . ?
C2 C1 1.3831(19) . ?
C13 C14 1.5087(15) . ?
C13 C12 1.5304(16) . ?
C9 C8 1.400(2) . ?
C7 C8 1.366(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
C7 N2 C5 130.53(11) . . ?
C7 N2 C10 108.64(11) . . ?
C5 N2 C10 120.81(10) . . ?
N1 C11 C10 122.68(10) . . ?
N1 C11 C12 117.63(11) . . ?
C10 C11 C12 119.61(11) . . ?
N2 C5 C6 122.43(10) . . ?
N2 C5 C4 116.85(10) . . ?
C6 C5 C4 120.72(11) . . ?
C11 N1 C4 118.75(10) . . ?
C1 C6 C5 117.73(11) . . ?
C2 C3 C4 121.16(11) . . ?
C3 C4 N1 118.58(10) . . ?
C3 C4 C5 118.68(11) . . ?
N1 C4 C5 122.73(11) . . ?
C9 C10 N2 107.37(11) . . ?
C9 C10 C11 134.54(12) . . ?
N2 C10 C11 118.06(11) . . ?
C3 C2 C1 118.13(12) . . ?
C14 C13 C12 113.82(10) . . ?
F1 C1 C6 118.54(11) . . ?
F1 C1 C2 117.89(12) . . ?
C6 C1 C2 123.57(11) . . ?
O1 C14 C13 110.52(10) . . ?
C11 C12 C13 109.86(9) . . ?
C10 C9 C8 107.34(12) . . ?
C8 C7 N2 107.85(12) . . ?
C7 C8 C9 108.80(13) . . ?

_refine_diff_density_max         0.170
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.040

