# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_zhou106s
_database_code_depnum_ccdc_archive 'CCDC 1890598'
loop_
_audit_author_name
_audit_author_address
Yongxin
;Nanyang Technological University
Singapore
;
_audit_update_record             
;
2021-09-17 deposited with the CCDC.	2021-10-06 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H16 F N O3'
_chemical_formula_iupac          ?
_chemical_formula_weight         265.28
_chemical_absolute_configuration ad

_chemical_melting_point          ?

_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
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                   5.1221(2)
_cell_length_b                   14.0899(5)
_cell_length_c                   18.2239(6)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1315.22(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4391
_cell_measurement_theta_min      3.9658
_cell_measurement_theta_max      66.4167
_cell_measurement_temperature    296.(2)

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.060
_exptl_crystal_size_min          0.040
_exptl_crystal_density_diffrn    1.340
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             560

_exptl_absorpt_coefficient_mu    0.867
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.65
_exptl_absorpt_correction_T_max  0.97

_exptl_special_details           
;
;

_diffrn_ambient_temperature      296.(2)

_diffrn_source                   'Incoatec Microfocus Source'
_diffrn_source_type              'Bruker Kappa Duo APEX2'

_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_monochromator  'Multilayer Mirror'

_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            6770
_diffrn_reflns_av_R_equivalents  0.0556
_diffrn_reflns_av_unetI/netI     0.0520
_diffrn_reflns_theta_min         3.97
_diffrn_reflns_theta_max         66.51
_diffrn_reflns_theta_full        66.51
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21

_reflns_number_total             2301
_reflns_number_gt                2119
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0444
_refine_ls_R_factor_gt           0.0410
_refine_ls_wR_factor_gt          0.1062
_refine_ls_wR_factor_ref         0.1105
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.062
_refine_ls_number_reflns         2301
_refine_ls_number_parameters     174
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0610P)²+0.0911P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.005
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.159
_refine_diff_density_min         -0.207
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 
;

Flack x determined using 796 quotients [(I+)-(I-)]/[(I+)+(I-)]
(Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.08(13)

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'
F F 0.0727 0.0534 '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'

_computing_data_collection       'APEX3 (Bruker AXS Inc., 2017)'
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution    'XT, VERSION 2014/5'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'XP (Bruker AXS Inc., 2017)'
_computing_publication_material  'APEX3 (Bruker AXS Inc., 2017)'

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C C1 0.1473(7) 0.63578(19) 0.76921(15) 0.0568(7) Uani d . . . 1 . .
H H1 0.164529 0.698016 0.752911 0.068 Uiso calc U . R 1 . .
C C2 -0.0053(7) 0.6159(2) 0.82839(16) 0.0622(8) Uani d . . . 1 . .
C C3 -0.0377(7) 0.5253(2) 0.85535(16) 0.0605(8) Uani d . . . 1 . .
H H3 -0.141821 0.513496 0.896143 0.073 Uiso calc U . R 1 . .
C C4 0.0903(6) 0.45299(18) 0.81949(15) 0.0513(6) Uani d . . . 1 . .
H H4 0.069487 0.391134 0.836304 0.062 Uiso calc U . R 1 . .
C C5 0.2498(5) 0.46920(17) 0.75898(14) 0.0438(6) Uani d . . . 1 . .
C C6 0.2781(5) 0.56225(17) 0.73299(14) 0.0429(6) Uani d . . . 1 . .
C C7 0.4579(5) 0.58333(18) 0.66902(15) 0.0463(6) Uani d . . . 1 . .
H H7 0.628129 0.598617 0.690554 0.056 Uiso calc U . R 1 . .
C C8 0.5030(5) 0.49699(19) 0.61968(16) 0.0482(6) Uani d . . . 1 . .
H H8 0.647615 0.512286 0.58652 0.058 Uiso calc U . R 1 . .
C C9 0.5906(6) 0.4138(2) 0.66809(17) 0.0562(7) Uani d . . . 1 . .
H H9A 0.634397 0.35992 0.637365 0.067 Uiso calc U . R 1 . .
H H9B 0.74569 0.431825 0.695288 0.067 Uiso calc U . R 1 . .
C C10 0.3760(7) 0.38599(19) 0.72132(16) 0.0558(7) Uani d . . . 1 . .
H H10A 0.243112 0.350841 0.694884 0.067 Uiso calc U . R 1 . .
H H10B 0.448809 0.344093 0.758274 0.067 Uiso calc U . R 1 . .
C C11 0.2708(5) 0.47167(18) 0.57308(14) 0.0437(6) Uani d . . . 1 . .
C C12 0.0945(8) 0.3601(3) 0.4904(2) 0.0785(10) Uani d . . . 1 . .
H H12A -0.063736 0.359913 0.518611 0.118 Uiso calc U . R 1 . .
H H12B 0.128894 0.297205 0.472589 0.118 Uiso calc U . R 1 . .
H H12C 0.075919 0.402666 0.449571 0.118 Uiso calc U . R 1 . .
C C13 0.5469(5) 0.73308(16) 0.60621(12) 0.0386(5) Uani d . . . 1 . .
C C14 0.4285(6) 0.81589(18) 0.56532(14) 0.0516(6) Uani d . . . 1 . .
H H14A 0.485694 0.874244 0.587258 0.077 Uiso calc U . R 1 . .
H H14B 0.241594 0.812033 0.567781 0.077 Uiso calc U . R 1 . .
H H14C 0.483047 0.814 0.51494 0.077 Uiso calc U . R 1 . .
F F1 -0.1299(6) 0.68850(14) 0.86347(13) 0.1017(9) Uani d . . . 1 . .
N N1 0.3761(4) 0.66798(14) 0.62904(13) 0.0485(5) Uani d . . . 1 . .
H H1A 0.212877 0.676157 0.619924 0.058 Uiso calc U . R 1 . .
O O1 0.7811(3) 0.72779(12) 0.61824(11) 0.0502(5) Uani d . . . 1 . .
O O2 0.3091(5) 0.39106(17) 0.53614(13) 0.0699(6) Uani d . . . 1 . .
O O3 0.0755(4) 0.51728(15) 0.56730(13) 0.0612(6) Uani d . . . 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C2 . 1.361(4) ?
C1 C6 . 1.399(4) ?
C1 H1 . 0.93 ?
C2 F1 . 1.365(4) ?
C2 C3 . 1.377(4) ?
C3 C4 . 1.377(4) ?
C3 H3 . 0.93 ?
C4 C5 . 1.391(4) ?
C4 H4 . 0.93 ?
C5 C6 . 1.402(3) ?
C5 C10 . 1.505(4) ?
C6 C7 . 1.515(4) ?
C7 N1 . 1.459(3) ?
C7 C8 . 1.530(4) ?
C7 H7 . 0.98 ?
C8 C11 . 1.504(4) ?
C8 C9 . 1.534(4) ?
C8 H8 . 0.98 ?
C9 C10 . 1.518(4) ?
C9 H9A . 0.97 ?
C9 H9B . 0.97 ?
C10 H10A . 0.97 ?
C10 H10B . 0.97 ?
C11 O3 . 1.193(3) ?
C11 O2 . 1.335(4) ?
C12 O2 . 1.447(4) ?
C12 H12A . 0.96 ?
C12 H12B . 0.96 ?
C12 H12C . 0.96 ?
C13 O1 . 1.222(3) ?
C13 N1 . 1.334(3) ?
C13 C14 . 1.511(3) ?
C14 H14A . 0.96 ?
C14 H14B . 0.96 ?
C14 H14C . 0.96 ?
N1 H1A . 0.86 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 C1 C6 . . 119.7(2) ?
C2 C1 H1 . . 120.1 ?
C6 C1 H1 . . 120.1 ?
C1 C2 F1 . . 119.0(3) ?
C1 C2 C3 . . 122.9(3) ?
F1 C2 C3 . . 118.1(3) ?
C4 C3 C2 . . 117.3(3) ?
C4 C3 H3 . . 121.3 ?
C2 C3 H3 . . 121.3 ?
C3 C4 C5 . . 122.3(2) ?
C3 C4 H4 . . 118.8 ?
C5 C4 H4 . . 118.8 ?
C4 C5 C6 . . 118.8(2) ?
C4 C5 C10 . . 119.1(2) ?
C6 C5 C10 . . 122.0(2) ?
C1 C6 C5 . . 118.9(2) ?
C1 C6 C7 . . 120.6(2) ?
C5 C6 C7 . . 120.4(2) ?
N1 C7 C6 . . 111.7(2) ?
N1 C7 C8 . . 113.6(2) ?
C6 C7 C8 . . 112.8(2) ?
N1 C7 H7 . . 106.0 ?
C6 C7 H7 . . 106.0 ?
C8 C7 H7 . . 106.0 ?
C11 C8 C7 . . 113.6(2) ?
C11 C8 C9 . . 112.0(2) ?
C7 C8 C9 . . 108.3(2) ?
C11 C8 H8 . . 107.6 ?
C7 C8 H8 . . 107.6 ?
C9 C8 H8 . . 107.6 ?
C10 C9 C8 . . 110.7(2) ?
C10 C9 H9A . . 109.5 ?
C8 C9 H9A . . 109.5 ?
C10 C9 H9B . . 109.5 ?
C8 C9 H9B . . 109.5 ?
H9A C9 H9B . . 108.1 ?
C5 C10 C9 . . 113.7(2) ?
C5 C10 H10A . . 108.8 ?
C9 C10 H10A . . 108.8 ?
C5 C10 H10B . . 108.8 ?
C9 C10 H10B . . 108.8 ?
H10A C10 H10B . . 107.7 ?
O3 C11 O2 . . 122.5(3) ?
O3 C11 C8 . . 125.8(2) ?
O2 C11 C8 . . 111.7(2) ?
O2 C12 H12A . . 109.5 ?
O2 C12 H12B . . 109.5 ?
H12A C12 H12B . . 109.5 ?
O2 C12 H12C . . 109.5 ?
H12A C12 H12C . . 109.5 ?
H12B C12 H12C . . 109.5 ?
O1 C13 N1 . . 123.1(2) ?
O1 C13 C14 . . 122.0(2) ?
N1 C13 C14 . . 114.9(2) ?
C13 C14 H14A . . 109.5 ?
C13 C14 H14B . . 109.5 ?
H14A C14 H14B . . 109.5 ?
C13 C14 H14C . . 109.5 ?
H14A C14 H14C . . 109.5 ?
H14B C14 H14C . . 109.5 ?
C13 N1 C7 . . 122.0(2) ?
C13 N1 H1A . . 119.0 ?
C7 N1 H1A . . 119.0 ?
C11 O2 C12 . . 115.8(2) ?

