# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_a
_audit_block_doi                 10.5517/ccdc.csd.cc1msk65
_database_code_depnum_ccdc_archive 'CCDC 1513147'
_audit_update_record             
;
2016-10-31 deposited with the CCDC.
2017-06-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H14 F2 N2 O2'
_chemical_formula_sum            'C15 H14 F2 N2 O2'
_chemical_formula_weight         292.28

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                   11.8627(7)
_cell_length_b                   7.5770(4)
_cell_length_c                   16.1929(9)
_cell_angle_alpha                90
_cell_angle_beta                 104.622(2)
_cell_angle_gamma                90
_cell_volume                     1408.34(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    9957
_cell_measurement_theta_min      2.45
_cell_measurement_theta_max      27.36

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_F_000             608
_exptl_transmission_factor_min   0.974
_exptl_transmission_factor_max   0.989
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.110
_shelx_estimated_absorpt_T_min   0.968
_shelx_estimated_absorpt_T_max   0.989
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   'SADABS, 2014/5'


_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'microfocus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            29584
_diffrn_reflns_av_unetI/netI     0.0271
_diffrn_reflns_av_R_equivalents  0.0494
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.986
_diffrn_reflns_theta_max         27.519
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             3227
_reflns_number_gt                2339
_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       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014 (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)+(0.1000P)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         3227
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0779
_refine_ls_R_factor_gt           0.0558
_refine_ls_wR_factor_ref         0.2025
_refine_ls_wR_factor_gt          0.1898
_refine_ls_goodness_of_fit_ref   1.454
_refine_ls_restrained_S_all      1.454
_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 0.88765(10) 0.65930(16) 0.50634(8) 0.0714(4) Uani 1 1 d . . . . .
O2 O 0.82550(12) 0.32277(15) 0.49796(8) 0.0589(4) Uani 1 1 d . . . . .
F2 F 0.82549(12) 0.68772(17) 0.36929(9) 0.0840(5) Uani 1 1 d . . . . .
O1 O 0.83975(16) 0.3415(2) 0.36353(10) 0.0833(5) Uani 1 1 d . . . . .
N2 N 0.44686(15) 0.8663(2) 0.62768(11) 0.0625(5) Uani 1 1 d . . . . .
C5 C 0.56451(15) 0.7611(2) 0.53692(11) 0.0460(4) Uani 1 1 d . . . . .
C6 C 0.67258(15) 0.7149(2) 0.52465(11) 0.0452(4) Uani 1 1 d . . . . .
H6A H 0.7389 0.7278 0.5694 0.054 Uiso 1 1 calc R U . . .
C7 C 0.68337(15) 0.6497(2) 0.44666(10) 0.0454(4) Uani 1 1 d . . . . .
N1 N 0.65302(17) 0.8706(3) 0.67792(11) 0.0737(6) Uani 1 1 d . . . . .
C4 C 0.55463(17) 0.8361(2) 0.61945(12) 0.0507(5) Uani 1 1 d . . . . .
C13 C 0.82537(16) 0.4050(3) 0.42713(12) 0.0540(5) Uani 1 1 d . . . . .
C10 C 0.46704(16) 0.7372(2) 0.46941(13) 0.0561(5) Uani 1 1 d . . . . .
H10A H 0.3936 0.7654 0.4763 0.067 Uiso 1 1 calc R U . . .
C8 C 0.58520(17) 0.6277(2) 0.37869(11) 0.0516(5) Uani 1 1 d . . . . .
C12 C 0.80294(18) 0.6032(2) 0.43742(12) 0.0551(5) Uani 1 1 d . . . . .
C9 C 0.47784(18) 0.6724(2) 0.39269(13) 0.0593(5) Uani 1 1 d . . . . .
H9A H 0.4111 0.6579 0.3485 0.071 Uiso 1 1 calc R U . . .
C14 C 0.8488(2) 0.1332(2) 0.50004(14) 0.0661(6) Uani 1 1 d . . . . .
H14A H 0.9082 0.1071 0.4702 0.079 Uiso 1 1 calc R U . . .
H14B H 0.7785 0.0692 0.4725 0.079 Uiso 1 1 calc R U . . .
C1 C 0.4393(2) 0.9378(3) 0.70151(15) 0.0719(6) Uani 1 1 d . . . . .
H1B H 0.3659 0.9602 0.7098 0.086 Uiso 1 1 calc R U . . .
C11 C 0.5889(2) 0.5615(3) 0.29126(12) 0.0717(6) Uani 1 1 d . . . . .
H11A H 0.6680 0.5358 0.2908 0.108 Uiso 1 1 calc R U . . .
H11B H 0.5428 0.4562 0.2781 0.108 Uiso 1 1 calc R U . . .
H11C H 0.5582 0.6504 0.2494 0.108 Uiso 1 1 calc R U . . .
C2 C 0.5349(2) 0.9792(3) 0.76514(15) 0.0759(7) Uani 1 1 d . . . . .
H2B H 0.5281 1.0298 0.8160 0.091 Uiso 1 1 calc R U . . .
C15 C 0.8889(2) 0.0806(3) 0.59018(14) 0.0777(7) Uani 1 1 d . . . . .
H15A H 0.9049 -0.0437 0.5936 0.117 Uiso 1 1 calc R U . . .
H15B H 0.9585 0.1445 0.6167 0.117 Uiso 1 1 calc R U . . .
H15C H 0.8294 0.1068 0.6190 0.117 Uiso 1 1 calc R U . . .
C3 C 0.6407(3) 0.9432(4) 0.75088(14) 0.0877(8) Uani 1 1 d . . . . .
H3A H 0.7074 0.9700 0.7934 0.105 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 C12 1.367(2) . ?
O2 C13 1.305(2) . ?
O2 C14 1.461(2) . ?
F2 C12 1.359(2) . ?
O1 C13 1.187(2) . ?
N2 C4 1.338(2) . ?
N2 C1 1.336(3) . ?
C5 C10 1.388(3) . ?
C5 C6 1.391(2) . ?
C5 C4 1.484(2) . ?
C6 C7 1.392(2) . ?
C6 H6A 0.9300 . ?
C7 C8 1.396(3) . ?
C7 C12 1.505(3) . ?
N1 C4 1.330(3) . ?
N1 C3 1.344(3) . ?
C13 C12 1.542(3) . ?
C10 C9 1.372(3) . ?
C10 H10A 0.9300 . ?
C8 C9 1.391(3) . ?
C8 C11 1.513(2) . ?
C9 H9A 0.9300 . ?
C14 C15 1.471(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C1 C2 1.362(3) . ?
C1 H1B 0.9300 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C2 C3 1.360(3) . ?
C2 H2B 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C3 H3A 0.9300 . ?

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
C13 O2 C14 116.60(14) . . ?
C4 N2 C1 116.11(19) . . ?
C10 C5 C6 117.99(16) . . ?
C10 C5 C4 121.32(16) . . ?
C6 C5 C4 120.68(16) . . ?
C7 C6 C5 121.21(17) . . ?
C7 C6 H6A 119.4 . . ?
C5 C6 H6A 119.4 . . ?
C6 C7 C8 120.56(16) . . ?
C6 C7 C12 118.56(16) . . ?
C8 C7 C12 120.88(15) . . ?
C4 N1 C3 115.83(19) . . ?
N2 C4 N1 125.75(17) . . ?
N2 C4 C5 116.74(17) . . ?
N1 C4 C5 117.50(15) . . ?
O1 C13 O2 126.89(18) . . ?
O1 C13 C12 123.72(18) . . ?
O2 C13 C12 109.39(13) . . ?
C9 C10 C5 120.68(17) . . ?
C9 C10 H10A 119.7 . . ?
C5 C10 H10A 119.7 . . ?
C9 C8 C7 117.28(16) . . ?
C9 C8 C11 118.52(18) . . ?
C7 C8 C11 124.19(17) . . ?
F2 C12 F1 105.15(14) . . ?
F2 C12 C7 110.73(16) . . ?
F1 C12 C7 111.29(14) . . ?
F2 C12 C13 107.24(14) . . ?
F1 C12 C13 106.24(16) . . ?
C7 C12 C13 115.56(14) . . ?
C10 C9 C8 122.26(18) . . ?
C10 C9 H9A 118.9 . . ?
C8 C9 H9A 118.9 . . ?
O2 C14 C15 107.51(16) . . ?
O2 C14 H14A 110.2 . . ?
C15 C14 H14A 110.2 . . ?
O2 C14 H14B 110.2 . . ?
C15 C14 H14B 110.2 . . ?
H14A C14 H14B 108.5 . . ?
N2 C1 C2 122.63(19) . . ?
N2 C1 H1B 118.7 . . ?
C2 C1 H1B 118.7 . . ?
C8 C11 H11A 109.5 . . ?
C8 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C8 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C1 C2 C3 116.9(2) . . ?
C1 C2 H2B 121.5 . . ?
C3 C2 H2B 121.5 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N1 C3 C2 122.7(2) . . ?
N1 C3 H3A 118.6 . . ?
C2 C3 H3A 118.6 . . ?

_refine_diff_density_max         0.257
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.044

_shelxl_version_number           2014-3



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: dichloromethane'
