# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1880341'
loop_
_audit_author_name
_audit_author_address
'Pradip Kumar Monda '
;Research scholar, IISER Bhopal
India
;
_audit_update_record             
;
2019-01-10 deposited with the CCDC.	2020-03-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H4 F N O2'
_chemical_formula_weight         165.12

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'
O O 0.0106 0.0060 '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'
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                   4.8425(7)
_cell_length_b                   24.450(4)
_cell_length_c                   5.7818(9)
_cell_angle_alpha                90
_cell_angle_beta                 99.096(5)
_cell_angle_gamma                90
_cell_volume                     675.95(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    764
_cell_measurement_theta_min      3.93
_cell_measurement_theta_max      29.75


_exptl_crystal_description       plate
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.623
_exptl_crystal_F_000             336
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.136
_shelx_estimated_absorpt_T_min   0.960
_shelx_estimated_absorpt_T_max   0.989
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.6303
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\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            6770
_diffrn_reflns_av_unetI/netI     0.0688
_diffrn_reflns_av_R_equivalents  0.0908
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_limit_l_max       7
_diffrn_reflns_theta_min         3.333
_diffrn_reflns_theta_max         26.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             1314
_reflns_number_gt                906
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0343P)²+0.9978P] 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         1314
_refine_ls_number_parameters     119
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1125
_refine_ls_R_factor_gt           0.0675
_refine_ls_wR_factor_ref         0.1328
_refine_ls_wR_factor_gt          0.1210
_refine_ls_goodness_of_fit_ref   1.125
_refine_ls_restrained_S_all      1.125
_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
O2A O 0.0185(6) 0.65917(11) 0.9561(4) 0.0222(7) Uani 0.873(3) 1 d . . P A 1
C2A C 0.1477(9) 0.66291(18) 0.7937(7) 0.0190(10) Uani 0.873(3) 1 d . . P A 1
C1A C 0.1133(7) 0.71005(13) 0.6084(5) 0.0099(7) Uani 0.873(3) 1 d . . P A 1
O2B O 0.088(4) 0.6212(8) 1.051(3) 0.0222(7) Uani 0.127(3) 1 d . . P A 2
C2B C 0.143(8) 0.6428(13) 0.864(6) 0.0190(10) Uani 0.127(3) 1 d . . P A 2
C1B C 0.020(5) 0.6929(10) 0.791(4) 0.0099(7) Uani 0.127(3) 1 d . . P A 2
F1 F 0.7841(4) 0.50345(8) 0.7677(3) 0.0317(6) Uani 1 1 d . . . . .
N1 N 0.2931(6) 0.69757(10) 0.4654(4) 0.0199(7) Uani 1 1 d . . . . .
H1 H 0.320588 0.718249 0.346541 0.024 Uiso 1 1 calc R U . A 1
O1 O -0.0448(5) 0.74880(10) 0.5936(4) 0.0287(6) Uani 1 1 d . . . . .
C3 C 0.3587(7) 0.62467(13) 0.7225(5) 0.0179(7) Uani 1 1 d . . . . .
C4 C 0.4346(7) 0.64827(13) 0.5222(5) 0.0178(7) Uani 1 1 d . . . . .
C5 C 0.6285(7) 0.62348(14) 0.4036(5) 0.0194(8) Uani 1 1 d . . . . .
H5 H 0.681531 0.639906 0.268322 0.023 Uiso 1 1 calc R U . . .
C6 C 0.7424(7) 0.57412(13) 0.4881(5) 0.0206(8) Uani 1 1 d . . . . .
H6 H 0.873812 0.555783 0.409692 0.025 Uiso 1 1 calc R U . . .
C7 C 0.6644(7) 0.55174(13) 0.6863(5) 0.0210(8) Uani 1 1 d . . . . .
C8 C 0.4720(7) 0.57555(13) 0.8075(5) 0.0199(8) Uani 1 1 d . . . . .
H8 H 0.420217 0.558913 0.942874 0.024 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
O2A C2A 1.211(5) . ?
C2A C3 1.491(5) . ?
C2A C1A 1.565(5) . ?
C1A O1 1.212(4) . ?
C1A N1 1.328(4) . ?
O2B C2B 1.27(3) . ?
C2B C1B 1.40(4) . ?
C2B C3 1.49(4) . ?
C1B O1 1.78(2) . ?
F1 C7 1.366(4) . ?
N1 C4 1.400(4) . ?
N1 H1 0.8800 . ?
C3 C8 1.378(4) . ?
C3 C4 1.394(4) . ?
C4 C5 1.387(4) . ?
C5 C6 1.384(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.375(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.380(4) . ?
C8 H8 0.9500 . ?

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
O2A C2A C3 128.9(4) . . ?
O2A C2A C1A 125.1(4) . . ?
C3 C2A C1A 106.0(3) . . ?
O1 C1A N1 127.2(3) . . ?
O1 C1A C2A 128.4(3) . . ?
N1 C1A C2A 104.4(3) . . ?
O2B C2B C1B 119(3) . . ?
O2B C2B C3 127(3) . . ?
C1B C2B C3 113(2) . . ?
C2B C1B O1 153(2) . . ?
C1A N1 C4 113.4(3) . . ?
C1A N1 H1 123.3 . . ?
C4 N1 H1 123.3 . . ?
C8 C3 C4 121.0(3) . . ?
C8 C3 C2A 134.4(3) . . ?
C4 C3 C2A 104.6(3) . . ?
C8 C3 C2B 109.7(13) . . ?
C4 C3 C2B 129.2(13) . . ?
C5 C4 C3 121.2(3) . . ?
C5 C4 N1 127.2(3) . . ?
C3 C4 N1 111.6(3) . . ?
C6 C5 C4 118.0(3) . . ?
C6 C5 H5 121.0 . . ?
C4 C5 H5 121.0 . . ?
C7 C6 C5 119.6(3) . . ?
C7 C6 H6 120.2 . . ?
C5 C6 H6 120.2 . . ?
F1 C7 C6 118.3(3) . . ?
F1 C7 C8 118.2(3) . . ?
C6 C7 C8 123.5(3) . . ?
C3 C8 C7 116.7(3) . . ?
C3 C8 H8 121.7 . . ?
C7 C8 H8 121.7 . . ?

_refine_diff_density_max         0.285
_refine_diff_density_min         -0.342
_refine_diff_density_rms         0.067

####################################################################### 
# 
# 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_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1880342'
loop_
_audit_author_name
_audit_author_address
'Pradip Kumar Monda '
;Research scholar, IISER Bhopal
India
;
_audit_update_record             
;
2019-01-10 deposited with the CCDC.	2020-03-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H10 F N O3 S'
_chemical_formula_weight         243.25

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   8.2627(6)
_cell_length_b                   8.3350(6)
_cell_length_c                   8.7473(6)
_cell_angle_alpha                91.177(2)
_cell_angle_beta                 117.067(2)
_cell_angle_gamma                97.410(3)
_cell_volume                     529.82(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7475
_cell_measurement_theta_min      3.44
_cell_measurement_theta_max      30.11

_exptl_crystal_description       rod
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.525
_exptl_crystal_F_000             252
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    0.310
_shelx_estimated_absorpt_T_min   0.860
_shelx_estimated_absorpt_T_max   0.973
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.6134
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\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            10169
_diffrn_reflns_av_unetI/netI     0.0401
_diffrn_reflns_av_R_equivalents  0.0431
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         2.474
_diffrn_reflns_theta_max         29.125
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             2844
_reflns_number_gt                2572
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0379P)²+0.2145P] 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         2844
_refine_ls_number_parameters     147
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0386
_refine_ls_R_factor_gt           0.0342
_refine_ls_wR_factor_ref         0.0874
_refine_ls_wR_factor_gt          0.0850
_refine_ls_goodness_of_fit_ref   1.084
_refine_ls_restrained_S_all      1.084
_refine_ls_shift/su_max          0.001
_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
S1 S 0.78400(4) 0.42830(3) 0.02172(4) 0.01160(9) Uani 1 1 d . . . . .
F1 F 1.10297(11) -0.09288(11) 0.14560(11) 0.02366(19) Uani 1 1 d . . . . .
O1 O 0.67547(13) 0.34409(12) 0.53715(13) 0.0206(2) Uani 1 1 d . . . . .
O2 O 0.54039(12) 0.10056(11) 0.23937(12) 0.0172(2) Uani 1 1 d . . . . .
O3 O 0.76031(12) 0.47941(11) 0.17723(11) 0.01535(19) Uani 1 1 d . . . . .
N1 N 0.95638(14) 0.32363(12) 0.54379(13) 0.0131(2) Uani 1 1 d . . . . .
H1 H 1.029829 0.395882 0.630510 0.016 Uiso 1 1 calc R U . . .
C1 C 0.77137(17) 0.28845(14) 0.48389(15) 0.0130(2) Uani 1 1 d . . . . .
C2 C 0.70093(16) 0.15634(14) 0.32941(15) 0.0115(2) Uani 1 1 d . . . . .
C3 C 0.86699(15) 0.12354(14) 0.32140(15) 0.0105(2) Uani 1 1 d . . . . .
C4 C 1.01505(16) 0.22930(14) 0.44887(15) 0.0110(2) Uani 1 1 d . . . . .
C5 C 1.19197(16) 0.23342(16) 0.46929(16) 0.0155(2) Uani 1 1 d . . . . .
H5 H 1.291508 0.309228 0.551618 0.019 Uiso 1 1 calc R U . . .
C6 C 1.21883(17) 0.12245(17) 0.36478(17) 0.0173(3) Uani 1 1 d . . . . .
H6 H 1.338726 0.120444 0.376776 0.021 Uiso 1 1 calc R U . . .
C7 C 1.07092(18) 0.01508(16) 0.24347(16) 0.0155(2) Uani 1 1 d . . . . .
C8 C 0.89185(16) 0.01348(15) 0.21512(16) 0.0133(2) Uani 1 1 d . . . . .
H8 H 0.791760 -0.058473 0.128250 0.016 Uiso 1 1 calc R U . . .
C9 C 0.7194(2) 0.58583(16) -0.11967(17) 0.0202(3) Uani 1 1 d . . . . .
H9A H 0.597616 0.607593 -0.140581 0.030 Uiso 1 1 calc R U . . .
H9B H 0.715643 0.551695 -0.229280 0.030 Uiso 1 1 calc R U . . .
H9C H 0.809591 0.684696 -0.066781 0.030 Uiso 1 1 calc R U . . .
C10 C 0.58986(17) 0.27776(15) -0.10601(16) 0.0157(2) Uani 1 1 d . . . . .
H10A H 0.596679 0.180311 -0.043878 0.023 Uiso 1 1 calc R U . . .
H10B H 0.589797 0.250079 -0.215472 0.023 Uiso 1 1 calc R U . . .
H10C H 0.476553 0.320267 -0.128804 0.023 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
S1 O3 1.5199(9) . ?
S1 C9 1.7847(13) . ?
S1 C10 1.7855(12) . ?
F1 C7 1.3597(14) . ?
O1 C1 1.2173(15) . ?
O2 C2 1.2129(15) . ?
N1 C1 1.3589(16) . ?
N1 C4 1.4072(15) . ?
N1 H1 0.8800 . ?
C1 C2 1.5605(16) . ?
C2 C3 1.4649(16) . ?
C3 C8 1.3912(16) . ?
C3 C4 1.3990(16) . ?
C4 C5 1.3854(16) . ?
C5 C6 1.3940(19) . ?
C5 H5 0.9500 . ?
C6 C7 1.3854(19) . ?
C6 H6 0.9500 . ?
C7 C8 1.3827(17) . ?
C8 H8 0.9500 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?

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
O3 S1 C9 106.31(6) . . ?
O3 S1 C10 105.95(5) . . ?
C9 S1 C10 97.21(6) . . ?
C1 N1 C4 111.08(10) . . ?
C1 N1 H1 124.5 . . ?
C4 N1 H1 124.5 . . ?
O1 C1 N1 128.76(12) . . ?
O1 C1 C2 125.28(11) . . ?
N1 C1 C2 105.95(10) . . ?
O2 C2 C3 130.67(11) . . ?
O2 C2 C1 124.43(11) . . ?
C3 C2 C1 104.89(9) . . ?
C8 C3 C4 121.66(11) . . ?
C8 C3 C2 131.41(11) . . ?
C4 C3 C2 106.94(10) . . ?
C5 C4 C3 121.10(11) . . ?
C5 C4 N1 127.84(11) . . ?
C3 C4 N1 111.06(10) . . ?
C4 C5 C6 117.67(11) . . ?
C4 C5 H5 121.2 . . ?
C6 C5 H5 121.2 . . ?
C7 C6 C5 120.09(11) . . ?
C7 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
F1 C7 C8 118.26(11) . . ?
F1 C7 C6 118.38(11) . . ?
C8 C7 C6 123.35(12) . . ?
C7 C8 C3 116.01(11) . . ?
C7 C8 H8 122.0 . . ?
C3 C8 H8 122.0 . . ?
S1 C9 H9A 109.5 . . ?
S1 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
S1 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
S1 C10 H10A 109.5 . . ?
S1 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
S1 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?

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
C4 N1 C1 O1 178.41(12) . . . . ?
C4 N1 C1 C2 -0.77(13) . . . . ?
O1 C1 C2 O2 4.1(2) . . . . ?
N1 C1 C2 O2 -176.71(11) . . . . ?
O1 C1 C2 C3 -176.99(12) . . . . ?
N1 C1 C2 C3 2.23(12) . . . . ?
O2 C2 C3 C8 -3.9(2) . . . . ?
C1 C2 C3 C8 177.25(12) . . . . ?
O2 C2 C3 C4 176.02(13) . . . . ?
C1 C2 C3 C4 -2.83(12) . . . . ?
C8 C3 C4 C5 2.86(18) . . . . ?
C2 C3 C4 C5 -177.07(11) . . . . ?
C8 C3 C4 N1 -177.53(10) . . . . ?
C2 C3 C4 N1 2.53(13) . . . . ?
C1 N1 C4 C5 178.49(12) . . . . ?
C1 N1 C4 C3 -1.09(14) . . . . ?
C3 C4 C5 C6 -3.44(17) . . . . ?
N1 C4 C5 C6 177.03(11) . . . . ?
C4 C5 C6 C7 1.18(18) . . . . ?
C5 C6 C7 F1 -179.09(11) . . . . ?
C5 C6 C7 C8 1.8(2) . . . . ?
F1 C7 C8 C3 178.48(10) . . . . ?
C6 C7 C8 C3 -2.43(18) . . . . ?
C4 C3 C8 C7 0.10(18) . . . . ?
C2 C3 C8 C7 -179.99(12) . . . . ?

_refine_diff_density_max         0.436
_refine_diff_density_min         -0.524
_refine_diff_density_rms         0.074

####################################################################### 
# 
# 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_shelx_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 1880344'
loop_
_audit_author_name
_audit_author_address
'Pradip Kumar Monda '
;Research scholar, IISER Bhopal
India
;
_audit_update_record             
;
2019-01-10 deposited with the CCDC.	2020-03-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H9 F N2 O4'
_chemical_formula_weight         288.23

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                   12.8358(7)
_cell_length_b                   6.1720(3)
_cell_length_c                   15.5627(8)
_cell_angle_alpha                90
_cell_angle_beta                 96.692(2)
_cell_angle_gamma                90
_cell_volume                     1224.52(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6886
_cell_measurement_theta_min      2.64
_cell_measurement_theta_max      29.87

_exptl_crystal_description       block
_exptl_crystal_colour            ?
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.563
_exptl_crystal_F_000             592
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.310
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.127
_shelx_estimated_absorpt_T_min   0.962
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.6486
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\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            16042
_diffrn_reflns_av_unetI/netI     0.0435
_diffrn_reflns_av_R_equivalents  0.0504
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.636
_diffrn_reflns_theta_max         30.035
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3561
_reflns_number_gt                2767
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0578P)²+0.3835P] 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         3561
_refine_ls_number_parameters     190
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0674
_refine_ls_R_factor_gt           0.0470
_refine_ls_wR_factor_ref         0.1166
_refine_ls_wR_factor_gt          0.1074
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_restrained_S_all      1.065
_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 0.25618(7) 0.26822(16) 0.36274(6) 0.0314(2) Uani 1 1 d . . . . .
O1 O 0.79270(8) -0.07452(17) 0.43962(6) 0.0206(2) Uani 1 1 d . . . . .
O2 O 0.67437(9) 0.31230(17) 0.48748(7) 0.0247(2) Uani 1 1 d . . . . .
O3 O 0.58470(7) 0.49066(14) 0.26203(6) 0.0169(2) Uani 1 1 d . . . . .
O4 O 0.71853(7) 0.25206(14) 0.27454(6) 0.0154(2) Uani 1 1 d . . . . .
N1 N 0.62766(9) -0.17432(17) 0.37533(7) 0.0140(2) Uani 1 1 d . . . . .
H1 H 0.642223 -0.301372 0.354012 0.017 Uiso 1 1 calc R U . . .
N2 N 0.60761(8) -0.02703(17) 0.16761(7) 0.0113(2) Uani 1 1 d . . . . .
H2 H 0.671916 -0.054844 0.191139 0.014 Uiso 1 1 calc R U . . .
C1 C 0.69945(11) -0.0440(2) 0.42053(8) 0.0153(3) Uani 1 1 d . . . . .
C2 C 0.63668(11) 0.1608(2) 0.44555(8) 0.0156(3) Uani 1 1 d . . . . .
C3 C 0.52820(10) 0.1204(2) 0.40812(8) 0.0132(3) Uani 1 1 d . . . . .
C4 C 0.52678(10) -0.0808(2) 0.36677(8) 0.0121(2) Uani 1 1 d . . . . .
C5 C 0.43531(10) -0.1669(2) 0.32436(9) 0.0160(3) Uani 1 1 d . . . . .
H5 H 0.434650 -0.303922 0.296453 0.019 Uiso 1 1 calc R U . . .
C6 C 0.34413(11) -0.0439(2) 0.32437(9) 0.0194(3) Uani 1 1 d . . . . .
H6 H 0.279576 -0.096819 0.296052 0.023 Uiso 1 1 calc R U . . .
C7 C 0.34751(11) 0.1552(2) 0.36555(9) 0.0195(3) Uani 1 1 d . . . . .
C8 C 0.43718(11) 0.2435(2) 0.40833(9) 0.0174(3) Uani 1 1 d . . . . .
H8 H 0.437173 0.380173 0.436385 0.021 Uiso 1 1 calc R U . . .
C9 C 0.62889(10) 0.3189(2) 0.24549(8) 0.0120(2) Uani 1 1 d . . . . .
C10 C 0.56456(10) 0.1659(2) 0.18378(8) 0.0115(2) Uani 1 1 d . . . . .
C11 C 0.46437(10) 0.2128(2) 0.14589(9) 0.0147(3) Uani 1 1 d . . . . .
H11 H 0.433410 0.348978 0.155820 0.018 Uiso 1 1 calc R U . . .
C12 C 0.40915(10) 0.0600(2) 0.09324(9) 0.0165(3) Uani 1 1 d . . . . .
H12 H 0.340231 0.091109 0.066943 0.020 Uiso 1 1 calc R U . . .
C13 C 0.45537(11) -0.1389(2) 0.07923(8) 0.0165(3) Uani 1 1 d . . . . .
H13 H 0.418082 -0.245935 0.044177 0.020 Uiso 1 1 calc R U . . .
C14 C 0.55650(10) -0.1781(2) 0.11718(8) 0.0137(3) Uani 1 1 d . . . . .
H14 H 0.589685 -0.312027 0.107495 0.016 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 C7 1.3605(15) . ?
O1 C1 1.2139(17) . ?
O2 C2 1.2087(17) . ?
O3 C9 1.2433(15) . ?
O4 C9 1.2559(16) . ?
N1 C1 1.3563(17) . ?
N1 C4 1.4098(16) . ?
N1 H1 0.8800 . ?
N2 C14 1.3400(16) . ?
N2 C10 1.3486(16) . ?
N2 H2 0.8800 . ?
C1 C2 1.5723(19) . ?
C2 C3 1.4667(19) . ?
C3 C8 1.3939(18) . ?
C3 C4 1.3975(18) . ?
C4 C5 1.3844(18) . ?
C5 C6 1.3954(19) . ?
C5 H5 0.9500 . ?
C6 C7 1.384(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.373(2) . ?
C8 H8 0.9500 . ?
C9 C10 1.5203(18) . ?
C10 C11 1.3815(18) . ?
C11 C12 1.3883(19) . ?
C11 H11 0.9500 . ?
C12 C13 1.392(2) . ?
C12 H12 0.9500 . ?
C13 C14 1.3834(19) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?

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
C1 N1 C4 111.55(11) . . ?
C1 N1 H1 124.2 . . ?
C4 N1 H1 124.2 . . ?
C14 N2 C10 122.70(11) . . ?
C14 N2 H2 118.6 . . ?
C10 N2 H2 118.6 . . ?
O1 C1 N1 128.76(13) . . ?
O1 C1 C2 125.67(12) . . ?
N1 C1 C2 105.56(11) . . ?
O2 C2 C3 130.37(13) . . ?
O2 C2 C1 124.84(13) . . ?
C3 C2 C1 104.78(11) . . ?
C8 C3 C4 121.29(12) . . ?
C8 C3 C2 131.57(12) . . ?
C4 C3 C2 107.14(11) . . ?
C5 C4 C3 121.72(12) . . ?
C5 C4 N1 127.32(12) . . ?
C3 C4 N1 110.96(11) . . ?
C4 C5 C6 117.10(12) . . ?
C4 C5 H5 121.5 . . ?
C6 C5 H5 121.5 . . ?
C7 C6 C5 120.15(13) . . ?
C7 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
F1 C7 C8 118.85(13) . . ?
F1 C7 C6 117.38(13) . . ?
C8 C7 C6 123.77(13) . . ?
C7 C8 C3 115.97(12) . . ?
C7 C8 H8 122.0 . . ?
C3 C8 H8 122.0 . . ?
O3 C9 O4 128.79(12) . . ?
O3 C9 C10 115.67(11) . . ?
O4 C9 C10 115.51(11) . . ?
N2 C10 C11 119.12(12) . . ?
N2 C10 C9 117.52(11) . . ?
C11 C10 C9 123.33(11) . . ?
C10 C11 C12 119.70(12) . . ?
C10 C11 H11 120.2 . . ?
C12 C11 H11 120.2 . . ?
C11 C12 C13 119.60(12) . . ?
C11 C12 H12 120.2 . . ?
C13 C12 H12 120.2 . . ?
C14 C13 C12 118.91(12) . . ?
C14 C13 H13 120.5 . . ?
C12 C13 H13 120.5 . . ?
N2 C14 C13 119.95(12) . . ?
N2 C14 H14 120.0 . . ?
C13 C14 H14 120.0 . . ?

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
C4 N1 C1 O1 179.96(13) . . . . ?
C4 N1 C1 C2 0.63(14) . . . . ?
O1 C1 C2 O2 -0.4(2) . . . . ?
N1 C1 C2 O2 178.92(13) . . . . ?
O1 C1 C2 C3 -179.80(12) . . . . ?
N1 C1 C2 C3 -0.45(13) . . . . ?
O2 C2 C3 C8 1.0(2) . . . . ?
C1 C2 C3 C8 -179.64(13) . . . . ?
O2 C2 C3 C4 -179.22(14) . . . . ?
C1 C2 C3 C4 0.11(13) . . . . ?
C8 C3 C4 C5 -0.06(19) . . . . ?
C2 C3 C4 C5 -179.84(11) . . . . ?
C8 C3 C4 N1 -179.96(11) . . . . ?
C2 C3 C4 N1 0.26(14) . . . . ?
C1 N1 C4 C5 179.51(12) . . . . ?
C1 N1 C4 C3 -0.60(15) . . . . ?
C3 C4 C5 C6 0.16(19) . . . . ?
N1 C4 C5 C6 -179.96(12) . . . . ?
C4 C5 C6 C7 0.0(2) . . . . ?
C5 C6 C7 F1 179.52(12) . . . . ?
C5 C6 C7 C8 -0.3(2) . . . . ?
F1 C7 C8 C3 -179.43(12) . . . . ?
C6 C7 C8 C3 0.4(2) . . . . ?
C4 C3 C8 C7 -0.22(19) . . . . ?
C2 C3 C8 C7 179.50(13) . . . . ?
C14 N2 C10 C11 -1.17(18) . . . . ?
C14 N2 C10 C9 177.17(11) . . . . ?
O3 C9 C10 N2 -176.70(11) . . . . ?
O4 C9 C10 N2 1.59(16) . . . . ?
O3 C9 C10 C11 1.58(18) . . . . ?
O4 C9 C10 C11 179.86(12) . . . . ?
N2 C10 C11 C12 1.11(19) . . . . ?
C9 C10 C11 C12 -177.14(12) . . . . ?
C10 C11 C12 C13 0.02(19) . . . . ?
C11 C12 C13 C14 -1.10(19) . . . . ?
C10 N2 C14 C13 0.07(19) . . . . ?
C12 C13 C14 N2 1.07(19) . . . . ?

_refine_diff_density_max         0.344
_refine_diff_density_min         -0.300
_refine_diff_density_rms         0.076

####################################################################### 
# 
# 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_shelx_CCDC3
_database_code_depnum_ccdc_archive 'CCDC 1880343'
loop_
_audit_author_name
_audit_author_address
'Pradip Kumar Monda '
;Research scholar, IISER Bhopal
India
;
_audit_update_record             
;
2019-01-10 deposited with the CCDC.	2020-03-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H4 F N O2'
_chemical_formula_weight         165.12

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                   3.7104(4)
_cell_length_b                   12.1407(15)
_cell_length_c                   14.7660(15)
_cell_angle_alpha                90
_cell_angle_beta                 93.397(4)
_cell_angle_gamma                90
_cell_volume                     663.99(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2178
_cell_measurement_theta_min      2.76
_cell_measurement_theta_max      30.10

_exptl_crystal_description       rod
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.652
_exptl_crystal_F_000             336
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    0.139
_shelx_estimated_absorpt_T_min   0.947
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_max  0.7460
_exptl_absorpt_correction_T_min  0.6537
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\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            7518
_diffrn_reflns_av_unetI/netI     0.0678
_diffrn_reflns_av_R_equivalents  0.0684
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.764
_diffrn_reflns_theta_max         29.563
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             1851
_reflns_number_gt                1235
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0400P)²+0.5801P] 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         1851
_refine_ls_number_parameters     109
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1060
_refine_ls_R_factor_gt           0.0599
_refine_ls_wR_factor_ref         0.1236
_refine_ls_wR_factor_gt          0.1089
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_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 0.3848(4) -0.03146(10) 0.76078(8) 0.0257(3) Uani 1 1 d . . . . .
O1 O 0.7444(4) 0.40808(12) 1.07744(10) 0.0229(4) Uani 1 1 d . . . . .
O2 O 0.9212(4) 0.17157(12) 1.07424(10) 0.0208(4) Uani 1 1 d . . . . .
N1 N 0.4638(5) 0.36561(14) 0.93758(11) 0.0172(4) Uani 1 1 d . . . . .
H1 H 0.378668 0.430907 0.921731 0.021 Uiso 1 1 calc R U . . .
C1 C 0.6531(6) 0.34446(17) 1.01644(13) 0.0169(4) Uani 1 1 d . . . . .
C2 C 0.7425(6) 0.21783(16) 1.01501(13) 0.0158(4) Uani 1 1 d . . . . .
C3 C 0.5785(5) 0.17860(16) 0.92869(13) 0.0140(4) Uani 1 1 d . . . . .
C4 C 0.4190(6) 0.26974(16) 0.88338(13) 0.0143(4) Uani 1 1 d . . . . .
C5 C 0.2514(6) 0.26064(17) 0.79824(13) 0.0147(4) Uani 1 1 d . . . . .
H5 H 0.144533 0.322749 0.768119 0.018 Uiso 1 1 calc R U . . .
C6 C 0.2438(6) 0.15729(17) 0.75779(13) 0.0169(4) Uani 1 1 d . . . . .
H6 H 0.131507 0.147747 0.698809 0.020 Uiso 1 1 calc R U . . .
C7 C 0.3999(6) 0.06842(16) 0.80348(14) 0.0170(4) Uani 1 1 d . . . . .
C8 C 0.5712(6) 0.07496(16) 0.88887(14) 0.0164(4) Uani 1 1 d . . . . .
H8 H 0.677502 0.012465 0.918542 0.020 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 C7 1.366(2) . ?
O1 C1 1.219(2) . ?
O2 C2 1.205(2) . ?
N1 C1 1.348(3) . ?
N1 C4 1.417(3) . ?
N1 H1 0.8800 . ?
C1 C2 1.573(3) . ?
C2 C3 1.459(3) . ?
C3 C8 1.388(3) . ?
C3 C4 1.405(3) . ?
C4 C5 1.374(3) . ?
C5 C6 1.389(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.382(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.380(3) . ?
C8 H8 0.9500 . ?

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
C1 N1 C4 111.66(16) . . ?
C1 N1 H1 124.2 . . ?
C4 N1 H1 124.2 . . ?
O1 C1 N1 128.68(19) . . ?
O1 C1 C2 125.42(18) . . ?
N1 C1 C2 105.90(16) . . ?
O2 C2 C3 131.68(19) . . ?
O2 C2 C1 123.59(18) . . ?
C3 C2 C1 104.68(16) . . ?
C8 C3 C4 120.99(18) . . ?
C8 C3 C2 131.47(19) . . ?
C4 C3 C2 107.51(17) . . ?
C5 C4 C3 121.83(18) . . ?
C5 C4 N1 127.93(18) . . ?
C3 C4 N1 110.24(17) . . ?
C4 C5 C6 117.55(19) . . ?
C4 C5 H5 121.2 . . ?
C6 C5 H5 121.2 . . ?
C7 C6 C5 119.88(19) . . ?
C7 C6 H6 120.1 . . ?
C5 C6 H6 120.1 . . ?
F1 C7 C8 118.47(18) . . ?
F1 C7 C6 117.59(18) . . ?
C8 C7 C6 123.94(19) . . ?
C7 C8 C3 115.80(18) . . ?
C7 C8 H8 122.1 . . ?
C3 C8 H8 122.1 . . ?

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
C4 N1 C1 O1 178.7(2) . . . . ?
C4 N1 C1 C2 -0.7(2) . . . . ?
O1 C1 C2 O2 -2.1(3) . . . . ?
N1 C1 C2 O2 177.3(2) . . . . ?
O1 C1 C2 C3 -179.7(2) . . . . ?
N1 C1 C2 C3 -0.3(2) . . . . ?
O2 C2 C3 C8 1.6(4) . . . . ?
C1 C2 C3 C8 178.9(2) . . . . ?
O2 C2 C3 C4 -176.2(2) . . . . ?
C1 C2 C3 C4 1.1(2) . . . . ?
C8 C3 C4 C5 -0.3(3) . . . . ?
C2 C3 C4 C5 177.82(19) . . . . ?
C8 C3 C4 N1 -179.68(19) . . . . ?
C2 C3 C4 N1 -1.6(2) . . . . ?
C1 N1 C4 C5 -177.9(2) . . . . ?
C1 N1 C4 C3 1.4(2) . . . . ?
C3 C4 C5 C6 0.1(3) . . . . ?
N1 C4 C5 C6 179.4(2) . . . . ?
C4 C5 C6 C7 0.3(3) . . . . ?
C5 C6 C7 F1 179.91(18) . . . . ?
C5 C6 C7 C8 -0.6(3) . . . . ?
F1 C7 C8 C3 179.88(18) . . . . ?
C6 C7 C8 C3 0.4(3) . . . . ?
C4 C3 C8 C7 0.1(3) . . . . ?
C2 C3 C8 C7 -177.5(2) . . . . ?

_refine_diff_density_max         0.355
_refine_diff_density_min         -0.338
_refine_diff_density_rms         0.079

