# Electronic Supplementary Material (ESI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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 1971981'
loop_
_audit_author_name
_audit_author_address
YHxl
;Lanzhou Institute of Chemical Physics (LICP), Chinese Academy of Science
China
;
_audit_update_record             
;
2019-12-14 deposited with the CCDC.	2020-07-01 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            'C7 H5 F2 N O'
_chemical_formula_weight         157.12

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/c'
_space_group_name_Hall           '-P 2ybc'

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

_cell_length_a                   4.3520(8)
_cell_length_b                   10.590(2)
_cell_length_c                   14.532(3)
_cell_angle_alpha                90
_cell_angle_beta                 98.269(2)
_cell_angle_gamma                90
_cell_volume                     662.8(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2841
_cell_measurement_theta_min      2.39
_cell_measurement_theta_max      29.19

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.575
_exptl_crystal_F_000             320
_exptl_transmission_factor_min   0.6581
_exptl_transmission_factor_max   0.7458
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.144
_shelx_estimated_absorpt_T_min   0.958
_shelx_estimated_absorpt_T_max   0.972
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   SADABS
_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  'Bruker APEX II area detector'
_diffrn_measurement_method       'ω scan'
_diffrn_detector_area_resol_mean 'fine-focus sealed tube'
_diffrn_reflns_number            5390
_diffrn_reflns_av_unetI/netI     0.0181
_diffrn_reflns_av_R_equivalents  0.0212
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.388
_diffrn_reflns_theta_max         29.202
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.930
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.930
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.930
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             1657
_reflns_number_gt                1397
_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 SMART APEX II'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  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+0.0580P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.138(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         1657
_refine_ls_number_parameters     101
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0474
_refine_ls_R_factor_gt           0.0407
_refine_ls_wR_factor_ref         0.1444
_refine_ls_wR_factor_gt          0.1345
_refine_ls_goodness_of_fit_ref   0.999
_refine_ls_restrained_S_all      0.999
_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 0.7121(3) 0.32715(13) 0.20012(9) 0.0505(3) Uani 1 1 d . . . . .
H1 H 0.5966 0.3690 0.2398 0.061 Uiso 1 1 calc R U . . .
C2 C 0.7817(3) 0.38089(11) 0.11955(9) 0.0468(3) Uani 1 1 d . . . . .
C3 C 0.9514(3) 0.32293(11) 0.05866(8) 0.0447(3) Uani 1 1 d . . . . .
H3 H 0.9908 0.3634 0.0048 0.054 Uiso 1 1 calc R U . . .
C4 C 1.0623(3) 0.20134(10) 0.08052(8) 0.0394(3) Uani 1 1 d . . . . .
C5 C 0.9981(3) 0.14223(12) 0.16101(9) 0.0462(3) Uani 1 1 d . . . . .
H5 H 1.0699 0.0610 0.1761 0.055 Uiso 1 1 calc R U . . .
C6 C 0.8255(3) 0.20693(13) 0.21793(8) 0.0504(4) Uani 1 1 d . . . . .
C7 C 1.3231(3) 0.16703(11) -0.05660(9) 0.0501(3) Uani 1 1 d . . . . .
H7 H 1.2493 0.2433 -0.0827 0.060 Uiso 1 1 calc R U . . .
F1 F 0.6745(2) 0.49894(8) 0.09830(6) 0.0695(4) Uani 1 1 d . . . . .
F2 F 0.7609(3) 0.14803(10) 0.29524(6) 0.0762(4) Uani 1 1 d . . . . .
N1 N 1.2423(2) 0.13345(9) 0.02480(7) 0.0445(3) Uani 1 1 d . . . . .
H1A H 1.3087 0.0611 0.0459 0.053 Uiso 1 1 calc R U . . .
O1 O 1.4894(3) 0.10263(9) -0.09884(6) 0.0603(3) Uani 1 1 d . . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0509(7) 0.0574(7) 0.0459(6) -0.0118(5) 0.0155(5) -0.0059(5)
C2 0.0504(7) 0.0401(6) 0.0509(7) -0.0053(5) 0.0102(5) -0.0015(5)
C3 0.0516(7) 0.0400(6) 0.0449(6) 0.0016(4) 0.0151(5) -0.0029(5)
C4 0.0384(6) 0.0406(6) 0.0401(6) -0.0022(4) 0.0086(4) -0.0048(4)
C5 0.0475(7) 0.0470(6) 0.0446(6) 0.0057(5) 0.0084(5) -0.0024(5)
C6 0.0522(7) 0.0620(8) 0.0385(6) 0.0026(5) 0.0117(5) -0.0084(6)
C7 0.0662(8) 0.0430(6) 0.0434(6) 0.0031(5) 0.0158(5) 0.0067(5)
F1 0.0903(7) 0.0449(5) 0.0788(6) -0.0002(4) 0.0312(5) 0.0140(4)
F2 0.0956(8) 0.0873(7) 0.0524(5) 0.0169(4) 0.0337(5) 0.0018(5)
N1 0.0511(6) 0.0386(5) 0.0463(6) 0.0033(4) 0.0151(4) 0.0028(4)
O1 0.0859(8) 0.0503(6) 0.0505(5) 0.0028(4) 0.0299(5) 0.0111(5)

_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 1.3742(18) . ?
C1 C6 1.3764(19) . ?
C1 H1 0.9300 . ?
C2 F1 1.3542(15) . ?
C2 C3 1.3760(17) . ?
C3 C4 1.3956(16) . ?
C3 H3 0.9300 . ?
C4 C5 1.3901(16) . ?
C4 N1 1.4031(15) . ?
C5 C6 1.3773(19) . ?
C5 H5 0.9300 . ?
C6 F2 1.3495(14) . ?
C7 O1 1.2222(16) . ?
C7 N1 1.3299(16) . ?
C7 H7 0.9300 . ?
N1 H1A 0.8600 . ?

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 115.24(12) . . ?
C2 C1 H1 122.4 . . ?
C6 C1 H1 122.4 . . ?
F1 C2 C1 117.76(11) . . ?
F1 C2 C3 117.66(11) . . ?
C1 C2 C3 124.58(12) . . ?
C2 C3 C4 117.73(11) . . ?
C2 C3 H3 121.1 . . ?
C4 C3 H3 121.1 . . ?
C5 C4 C3 120.15(11) . . ?
C5 C4 N1 116.83(11) . . ?
C3 C4 N1 123.02(10) . . ?
C6 C5 C4 118.32(12) . . ?
C6 C5 H5 120.8 . . ?
C4 C5 H5 120.8 . . ?
F2 C6 C1 118.17(12) . . ?
F2 C6 C5 117.84(12) . . ?
C1 C6 C5 123.98(12) . . ?
O1 C7 N1 123.29(12) . . ?
O1 C7 H7 118.4 . . ?
N1 C7 H7 118.4 . . ?
C7 N1 C4 128.11(10) . . ?
C7 N1 H1A 115.9 . . ?
C4 N1 H1A 115.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 F1 179.67(11) . . . . ?
C6 C1 C2 C3 0.0(2) . . . . ?
F1 C2 C3 C4 179.92(10) . . . . ?
C1 C2 C3 C4 -0.4(2) . . . . ?
C2 C3 C4 C5 0.59(18) . . . . ?
C2 C3 C4 N1 -178.89(11) . . . . ?
C3 C4 C5 C6 -0.37(18) . . . . ?
N1 C4 C5 C6 179.15(10) . . . . ?
C2 C1 C6 F2 -178.93(11) . . . . ?
C2 C1 C6 C5 0.2(2) . . . . ?
C4 C5 C6 F2 179.11(10) . . . . ?
C4 C5 C6 C1 -0.1(2) . . . . ?
O1 C7 N1 C4 177.72(12) . . . . ?
C5 C4 N1 C7 176.93(12) . . . . ?
C3 C4 N1 C7 -3.6(2) . . . . ?

_refine_diff_density_max         0.196
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.040

_shelx_res_file                  
;

    1.res created by SHELXL-2014/7

TITL 1 in P2(1)/c
CELL 0.71073   4.3520  10.5896  14.5323  90.000  98.269  90.000
ZERR   4.00   0.0008   0.0020   0.0028   0.000   0.002   0.000
LATT 1
SYMM -X, 0.5+Y, 0.5-Z
SFAC C  H  N  O  F
UNIT 28  20  4  4  8
L.S. 10
ACTA
BOND $H
FMAP 2
PLAN 20
CONF
SIZE 0.30 0.20 0.20
TEMP 23.000
WGHT    0.100000    0.058000
EXTI    0.138150
FVAR       0.39046
MOLE 1
C1    1    0.712110    0.327153    0.200119    11.00000    0.05087    0.05743 =
         0.04585   -0.01176    0.01554   -0.00590
AFIX  43
H1    2    0.596634    0.369033    0.239788    11.00000   -1.20000
AFIX   0
C2    1    0.781677    0.380894    0.119552    11.00000    0.05038    0.04010 =
         0.05085   -0.00535    0.01020   -0.00146
C3    1    0.951405    0.322931    0.058658    11.00000    0.05161    0.04003 =
         0.04486    0.00162    0.01506   -0.00289
AFIX  43
H3    2    0.990845    0.363397    0.004776    11.00000   -1.20000
AFIX   0
C4    1    1.062339    0.201345    0.080519    11.00000    0.03843    0.04065 =
         0.04012   -0.00218    0.00861   -0.00481
C5    1    0.998138    0.142225    0.161014    11.00000    0.04748    0.04703 =
         0.04460    0.00570    0.00839   -0.00240
AFIX  43
H5    2    1.069941    0.061039    0.176052    11.00000   -1.20000
AFIX   0
C6    1    0.825495    0.206929    0.217933    11.00000    0.05223    0.06204 =
         0.03853    0.00258    0.01170   -0.00843
C7    1    1.323072    0.167029   -0.056602    11.00000    0.06616    0.04305 =
         0.04340    0.00312    0.01576    0.00665
AFIX  43
H7    2    1.249256    0.243339   -0.082689    11.00000   -1.20000
AFIX   0
F1    5    0.674533    0.498937    0.098304    11.00000    0.09035    0.04493 =
         0.07875   -0.00018    0.03123    0.01403
F2    5    0.760897    0.148031    0.295241    11.00000    0.09555    0.08734 =
         0.05235    0.01691    0.03366    0.00175
N1    3    1.242329    0.133450    0.024796    11.00000    0.05112    0.03864 =
         0.04626    0.00334    0.01515    0.00284
AFIX  43
H1A   2    1.308737    0.061077    0.045917    11.00000   -1.20000
AFIX   0
O1    4    1.489421    0.102630   -0.098841    11.00000    0.08590    0.05034 =
         0.05052    0.00283    0.02987    0.01109
HKLF 4

REM  1 in P2(1)/c
REM R1 =  0.0407 for    1397 Fo > 4sig(Fo)  and  0.0474 for all    1657 data
REM    101 parameters refined using      0 restraints

END

WGHT      0.0620      0.0976

REM Highest difference peak  0.196,  deepest hole -0.180,  1-sigma level  0.040
Q1    1   0.7942  0.3382  0.0767  11.00000  0.05    0.20
Q2    1   0.9535  0.2526  0.0599  11.00000  0.05    0.19
Q3    1   0.7650  0.3442  0.1618  11.00000  0.05    0.19
Q4    1   0.6963  0.2584  0.1914  11.00000  0.05    0.18
Q5    1   1.0219  0.1749  0.1165  11.00000  0.05    0.16
Q6    1   0.9310  0.3575  0.0993  11.00000  0.05    0.16
Q7    1   1.5065  0.0236 -0.0998  11.00000  0.05    0.15
Q8    1   0.8321  0.1658  0.1761  11.00000  0.05    0.14
Q9    1   0.9585  0.1940  0.1968  11.00000  0.05    0.14
Q10   1   1.0598  0.2178 -0.0982  11.00000  0.05    0.12
Q11   1   0.7307  0.0535  0.2772  11.00000  0.05    0.11
Q12   1   0.7149  0.4222  0.1101  11.00000  0.05    0.11
Q13   1   0.6514  0.1003  0.2494  11.00000  0.05    0.10
Q14   1   1.0067  0.0042  0.1654  11.00000  0.05    0.09
Q15   1   1.3581  0.2737 -0.0558  11.00000  0.05    0.09
Q16   1   1.7272  0.0570 -0.0769  11.00000  0.05    0.09
Q17   1   0.7768  0.0155  0.1258  11.00000  0.05    0.09
Q18   1   0.9504  0.0329  0.1508  11.00000  0.05    0.09
Q19   1   1.4637  0.0541  0.0700  11.00000  0.05    0.09
Q20   1   0.8668  0.5577  0.0571  11.00000  0.05    0.08
;
_shelx_res_checksum              59690
