# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2019

####################################################################### 
# 
# 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 1937396'
_audit_update_record             
;
2019-07-01 deposited with the CCDC.	2019-07-31 downloaded from the CCDC.
;
_audit_creation_date             2019-02-27
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         '0.2(C10 H9 F3 N2 O)'
_chemical_formula_sum            'C2 H1.80 F0.60 N0.40 O0.20'
_chemical_formula_weight         46.04
_chemical_absolute_configuration unk
_chemical_melting_point          ?
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'
F F 0.0171 0.0103 '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'

_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'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 'x, y, z'
2 '-x+1/2, -y, z+1/2'
3 'x+1/2, -y+1/2, -z'
4 '-x, y+1/2, -z+1/2'

_cell_length_a                   7.1385(9)
_cell_length_b                   7.5039(10)
_cell_length_c                   19.126(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1024.5(2)
_cell_formula_units_Z            20
_cell_measurement_reflns_used    915
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      18.803
_cell_measurement_theta_min      2.916
_exptl_absorpt_coefficient_mu    0.135
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  0.127038
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   ?
_exptl_crystal_colour            white
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.492
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             472
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_special_details           
;
 ? 
;
_diffrn_reflns_av_R_equivalents  0.0518
_diffrn_reflns_av_unetI/netI     0.0692
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5878
_diffrn_reflns_theta_full        26.42
_diffrn_reflns_theta_max         26.42
_diffrn_reflns_theta_min         2.13
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_decay_%        ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_number         ?
_reflns_number_gt                1284
_reflns_number_total             2087
_reflns_threshold_expression     >2sigma(I)
_computing_cell_refinement       'SAINT v6.45A (Bruker, 2003)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v6.45A (Bruker, 2003)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_refine_diff_density_max         0.138
_refine_diff_density_min         -0.165
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.4(12)
_refine_ls_extinction_coef       ?
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.933
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     145
_refine_ls_number_reflns         2087
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0883
_refine_ls_R_factor_gt           0.0458
_refine_ls_restrained_S_all      0.933
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0473P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0892
_refine_ls_wR_factor_ref         0.1034
_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
2.b Aromatic/amide H refined with riding coordinates:
 N2(H2), N6(H6), C11(H11), C13(H13), C14(H14), C15(H15), C16(H16)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
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_calc_flag
_atom_site_disorder_assembly
_atom_site_disorder_group
_atom_site_refinement_flags_posn
O1 O -0.4954(2) -0.7240(3) -0.01572(10) 0.0602(6) Uani 1 d . . .
N2 N -0.6465(3) -0.8822(3) 0.06984(11) 0.0511(6) Uani 1 d . . .
H2 H -0.7526 -0.8283 0.0674 0.061 Uiso 1 calc . . R
F3 F -0.8878(2) -1.1791(3) 0.08164(9) 0.0805(6) Uani 1 d . . .
C4 C -0.6855(4) -1.0072(3) 0.18939(13) 0.0400(6) Uani 1 d . . .
F5 F -0.6460(3) -1.2239(3) 0.01831(9) 0.1020(7) Uani 1 d . . .
N6 N -0.3490(3) -0.9328(3) 0.05249(12) 0.0535(6) Uani 1 d . . .
H6 H -0.2401 -0.9273 0.0334 0.064 Uiso 1 calc . . R
F7 F -0.6667(3) -1.3436(2) 0.11966(11) 0.0880(7) Uani 1 d . . .
C8 C -0.3929(4) -1.0464(4) 0.11092(16) 0.0512(7) Uani 1 d . . .
H8A H -0.3332 -1.0043 0.1534 0.061 Uiso 1 calc . . R
H8B H -0.3542 -1.1683 0.1021 0.061 Uiso 1 calc . . R
C9 C -0.4954(4) -0.8370(4) 0.03118(14) 0.0442(6) Uani 1 d . . .
C10 C -0.6103(4) -1.0316(3) 0.11598(14) 0.0420(6) Uani 1 d . . .
C11 C -0.8381(4) -0.8975(4) 0.20202(14) 0.0549(8) Uani 1 d . . .
H11 H -0.8917 -0.8345 0.1652 0.066 Uiso 1 calc . . R
C12 C -0.7016(4) -1.1955(5) 0.08375(16) 0.0617(8) Uani 1 d . . .
C13 C -0.6827(5) -1.0791(4) 0.31185(15) 0.0668(9) Uani 1 d . . .
H13 H -0.6291 -1.1402 0.3491 0.080 Uiso 1 calc . . R
C14 C -0.9112(5) -0.8804(4) 0.26837(17) 0.0688(9) Uani 1 d . . .
H14 H -1.0137 -0.8064 0.2760 0.083 Uiso 1 calc . . R
C15 C -0.6080(4) -1.0977(4) 0.24527(15) 0.0562(8) Uani 1 d . . .
H15 H -0.5052 -1.1716 0.2382 0.067 Uiso 1 calc . . R
C16 C -0.8337(6) -0.9720(4) 0.32303(16) 0.0716(10) Uani 1 d . . .
H16 H -0.8841 -0.9611 0.3677 0.086 Uiso 1 calc . . R


_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
O1 C9 1.234(3) . ?
N2 C9 1.351(3) . ?
N2 C10 1.450(3) . ?
F3 C12 1.336(3) . ?
C4 C10 1.514(4) . ?
C4 C11 1.386(4) . ?
C4 C15 1.382(4) . ?
F5 C12 1.330(3) . ?
N6 C8 1.440(3) . ?
N6 C9 1.332(3) . ?
F7 C12 1.330(4) . ?
C8 C10 1.559(3) . ?
C10 C12 1.523(4) . ?
C11 C14 1.378(4) . ?
C13 C15 1.387(4) . ?
C13 C16 1.362(5) . ?
C14 C16 1.368(4) . ?

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
C9 N2 C10 112.7(2) . . ?
C11 C4 C10 120.8(2) . . ?
C15 C4 C10 121.0(2) . . ?
C15 C4 C11 118.1(3) . . ?
C9 N6 C8 112.7(2) . . ?
N6 C8 C10 102.8(2) . . ?
O1 C9 N2 124.8(2) . . ?
O1 C9 N6 126.3(3) . . ?
N6 C9 N2 108.9(2) . . ?
N2 C10 C4 114.1(2) . . ?
N2 C10 C8 101.2(2) . . ?
N2 C10 C12 107.6(2) . . ?
C4 C10 C8 114.8(2) . . ?
C4 C10 C12 108.7(2) . . ?
C12 C10 C8 110.1(2) . . ?
C14 C11 C4 120.9(3) . . ?
F3 C12 C10 111.3(3) . . ?
F5 C12 F3 106.4(3) . . ?
F5 C12 C10 112.5(2) . . ?
F7 C12 F3 106.2(2) . . ?
F7 C12 F5 107.2(3) . . ?
F7 C12 C10 112.7(2) . . ?
C16 C13 C15 120.5(3) . . ?
C16 C14 C11 120.3(3) . . ?
C4 C15 C13 120.4(3) . . ?
C13 C16 C14 119.8(3) . . ?


_olex2_submission_special_instructions 'No special instructions were received'
