# Electronic Supplementary Material (ESI) for Chemical Science.
# 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 
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data_cu_180522A_0m
_database_code_depnum_ccdc_archive 'CCDC 1845389'
_audit_update_record             
;
2018-05-25 deposited with the CCDC.
2018-10-03 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT029_cu_180522A_0m       
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.947 Why?  
RESPONSE: This is due to the weak diffraction ability of the 
crystal slected for X-ray experiment.
;

_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            'C12 H14 F N O3'
_chemical_formula_weight         239.24

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

_cell_length_a                   8.9101(3)
_cell_length_b                   9.4553(3)
_cell_length_c                   14.4099(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1214.00(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    7918
_cell_measurement_theta_min      4.68
_cell_measurement_theta_max      64.38

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.309
_exptl_crystal_F_000             504
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.10
_exptl_absorpt_coefficient_mu    0.880
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   none
_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     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8487
_diffrn_reflns_av_unetI/netI     0.0256
_diffrn_reflns_av_R_equivalents  0.0326
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         5.596
_diffrn_reflns_theta_max         64.854
_diffrn_reflns_theta_full        64.854
_diffrn_measured_fraction_theta_max 0.946
_diffrn_measured_fraction_theta_full 0.947
_diffrn_reflns_Laue_measured_fraction_max 0.946
_diffrn_reflns_Laue_measured_fraction_full 0.947
_diffrn_reflns_point_group_measured_fraction_max 0.938
_diffrn_reflns_point_group_measured_fraction_full 0.939
_reflns_number_total             1933
_reflns_number_gt                1922
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.690
_reflns_Friedel_fraction_max     0.927
_reflns_Friedel_fraction_full    0.928

_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-2014/7 (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)+(0.0495P)²+0.1382P] 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     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.120(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
; 
 Flack x determined using 779 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259). 
;
_refine_ls_abs_structure_Flack   0.03(5)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         1933
_refine_ls_number_parameters     160
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0337
_refine_ls_R_factor_gt           0.0336
_refine_ls_wR_factor_ref         0.0874
_refine_ls_wR_factor_gt          0.0873
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_restrained_S_all      1.088
_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 0.7277(2) 0.6592(2) 0.86927(15) 0.0473(5) Uani 1 1 d . . . . .
C2 C 0.7943(3) 0.7615(3) 0.92293(18) 0.0624(6) Uani 1 1 d . . . . .
H2 H 0.8505 0.8325 0.8950 0.075 Uiso 1 1 calc R U . . .
C3 C 0.7780(4) 0.7594(4) 1.01837(19) 0.0737(8) Uani 1 1 d . . . . .
H3 H 0.8224 0.8296 1.0543 0.088 Uiso 1 1 calc R U . . .
C4 C 0.6967(3) 0.6542(4) 1.06024(19) 0.0720(8) Uani 1 1 d . . . . .
H4 H 0.6865 0.6526 1.1245 0.086 Uiso 1 1 calc R U . . .
C5 C 0.6311(3) 0.5522(4) 1.00762(19) 0.0751(8) Uani 1 1 d . . . . .
H5 H 0.5761 0.4807 1.0360 0.090 Uiso 1 1 calc R U . . .
C6 C 0.6455(3) 0.5540(3) 0.91264(18) 0.0636(7) Uani 1 1 d . . . . .
H6 H 0.5996 0.4841 0.8773 0.076 Uiso 1 1 calc R U . . .
C7 C 0.7383(2) 0.6597(2) 0.76407(15) 0.0451(5) Uani 1 1 d . . . . .
H7 H 0.7217 0.5624 0.7430 0.054 Uiso 1 1 calc R U . . .
C8 C 0.6158(3) 0.7510(3) 0.72099(17) 0.0547(6) Uani 1 1 d . . . . .
H8 H 0.5206 0.7284 0.7516 0.066 Uiso 1 1 calc R U . . .
C9 C 0.5965(2) 0.7289(3) 0.61758(16) 0.0531(6) Uani 1 1 d . . . . .
C10 C 0.4902(4) 0.5741(4) 0.5076(2) 0.0870(10) Uani 1 1 d . . . . .
H10A H 0.4230 0.6433 0.4821 0.131 Uiso 1 1 calc R U . . .
H10B H 0.4437 0.4826 0.5054 0.131 Uiso 1 1 calc R U . . .
H10C H 0.5812 0.5725 0.4720 0.131 Uiso 1 1 calc R U . . .
C11 C 0.9992(2) 0.6114(2) 0.72777(13) 0.0406(5) Uani 1 1 d . . . . .
C12 C 1.1469(3) 0.6690(3) 0.69586(17) 0.0544(6) Uani 1 1 d . . . . .
H12A H 1.2251 0.6355 0.7360 0.082 Uiso 1 1 calc R U . . .
H12B H 1.1441 0.7705 0.6975 0.082 Uiso 1 1 calc R U . . .
H12C H 1.1662 0.6380 0.6336 0.082 Uiso 1 1 calc R U . . .
F1 F 0.6472(2) 0.89196(17) 0.73654(13) 0.0812(6) Uani 1 1 d . . . . .
N1 N 0.88382(19) 0.70364(18) 0.72947(12) 0.0422(4) Uani 1 1 d D . . . .
H1A H 0.907(3) 0.7921(15) 0.7265(17) 0.051 Uiso 1 1 d D U . . .
O1 O 0.6381(2) 0.8084(2) 0.55952(14) 0.0805(6) Uani 1 1 d . . . . .
O2 O 0.5243(2) 0.6100(2) 0.60291(12) 0.0699(5) Uani 1 1 d . . . . .
O3 O 0.98240(19) 0.48749(16) 0.74874(13) 0.0593(5) 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 C2 1.373(3) . ?
C1 C6 1.384(3) . ?
C1 C7 1.519(3) . ?
C2 C3 1.383(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.371(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.358(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.375(4) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 N1 1.450(3) . ?
C7 C8 1.524(3) . ?
C7 H7 0.9800 . ?
C8 F1 1.380(3) . ?
C8 C9 1.515(3) . ?
C8 H8 0.9800 . ?
C9 O1 1.184(3) . ?
C9 O2 1.312(3) . ?
C10 O2 1.448(3) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 O3 1.219(3) . ?
C11 N1 1.348(3) . ?
C11 C12 1.497(3) . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
N1 H1A 0.862(13) . ?

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 118.7(2) . . ?
C2 C1 C7 122.2(2) . . ?
C6 C1 C7 119.1(2) . . ?
C1 C2 C3 120.3(2) . . ?
C1 C2 H2 119.8 . . ?
C3 C2 H2 119.8 . . ?
C4 C3 C2 120.2(3) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C5 C4 C3 119.8(2) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
C4 C5 C6 120.5(3) . . ?
C4 C5 H5 119.8 . . ?
C6 C5 H5 119.8 . . ?
C5 C6 C1 120.5(3) . . ?
C5 C6 H6 119.7 . . ?
C1 C6 H6 119.7 . . ?
N1 C7 C1 113.56(17) . . ?
N1 C7 C8 109.73(18) . . ?
C1 C7 C8 111.33(17) . . ?
N1 C7 H7 107.3 . . ?
C1 C7 H7 107.3 . . ?
C8 C7 H7 107.3 . . ?
F1 C8 C9 108.4(2) . . ?
F1 C8 C7 109.65(18) . . ?
C9 C8 C7 113.84(19) . . ?
F1 C8 H8 108.3 . . ?
C9 C8 H8 108.3 . . ?
C7 C8 H8 108.3 . . ?
O1 C9 O2 125.7(2) . . ?
O1 C9 C8 124.9(2) . . ?
O2 C9 C8 109.4(2) . . ?
O2 C10 H10A 109.5 . . ?
O2 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
O2 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
O3 C11 N1 121.59(19) . . ?
O3 C11 C12 122.24(19) . . ?
N1 C11 C12 116.15(18) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C11 N1 C7 120.15(17) . . ?
C11 N1 H1A 116.4(17) . . ?
C7 N1 H1A 120.6(17) . . ?
C9 O2 C10 117.2(2) . . ?

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
C10 H10A O1 0.96 2.65 3.466(4) 143.3 4_466
C12 H12A F1 0.96 2.60 3.343(3) 134.6 3_746
C12 H12B O3 0.96 2.47 3.321(3) 148.3 3_756
N1 H1A O3 0.862(13) 2.125(15) 2.953(2) 161(2) 3_756

_refine_diff_density_max         0.157
_refine_diff_density_min         -0.173
_refine_diff_density_rms         0.041

