# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_dd19330
_database_code_depnum_ccdc_archive 'CCDC 1971638'
loop_
_audit_author_name
_audit_author_address
'Jiuxi Chen'
;Wenzhou University
China
;
_audit_update_record             
;
2019-12-12 deposited with the CCDC.	2020-02-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H15 F3 N2 O'
_chemical_formula_weight         392.37

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                   19.7618(6)
_cell_length_b                   5.1518(2)
_cell_length_c                   19.2059(8)
_cell_angle_alpha                90
_cell_angle_beta                 114.9310(10)
_cell_angle_gamma                90
_cell_volume                     1773.12(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    193(2)
_cell_measurement_reflns_used    7344
_cell_measurement_theta_min      4.546
_cell_measurement_theta_max      54.570

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.470
_exptl_crystal_F_000             808
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    0.113
_shelx_estimated_absorpt_T_min   0.978
_shelx_estimated_absorpt_T_max   0.985
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.3895
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      193(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            16683
_diffrn_reflns_av_unetI/netI     0.0486
_diffrn_reflns_av_R_equivalents  0.0666
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.273
_diffrn_reflns_theta_max         25.495
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             3278
_reflns_number_gt                2671
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_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)+(0.0505P)²+0.7193P] 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     SHELXL
_refine_ls_extinction_coef       0.043(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3278
_refine_ls_number_parameters     327
_refine_ls_number_restraints     108
_refine_ls_R_factor_all          0.0586
_refine_ls_R_factor_gt           0.0474
_refine_ls_wR_factor_ref         0.1282
_refine_ls_wR_factor_gt          0.1176
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.140
_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
N1 N 0.21827(8) 0.8822(3) 0.29322(8) 0.0353(4) Uani 1 1 d . . . . .
N2 N 0.08360(8) 1.1938(3) 0.22806(9) 0.0374(4) Uani 1 1 d . . . . .
O1 O 0.13965(6) 0.5730(2) 0.10425(7) 0.0373(3) Uani 1 1 d . . . . .
C1 C 0.17791(10) 0.3731(3) 0.08828(10) 0.0364(4) Uani 1 1 d . . . . .
C2 C 0.15358(11) 0.2437(4) 0.01927(11) 0.0437(5) Uani 1 1 d . . . . .
H2 H 0.1083 0.2880 -0.0232 0.052 Uiso 1 1 calc R U . . .
C3 C 0.19915(11) 0.0447(4) 0.01547(12) 0.0476(5) Uani 1 1 d . . . . .
H3 H 0.1850 -0.0492 -0.0311 0.057 Uiso 1 1 calc R U . . .
C4 C 0.26509(11) -0.0213(4) 0.07817(12) 0.0463(5) Uani 1 1 d . . . . .
H4 H 0.2943 -0.1614 0.0737 0.056 Uiso 1 1 calc R U . . .
C5 C 0.28887(10) 0.1125(4) 0.14645(11) 0.0413(5) Uani 1 1 d . . . . .
H5 H 0.3342 0.0680 0.1888 0.050 Uiso 1 1 calc R U . . .
C6 C 0.24433(10) 0.3156(3) 0.15150(10) 0.0357(4) Uani 1 1 d . . . . .
C7 C 0.24818(9) 0.4947(3) 0.21078(10) 0.0342(4) Uani 1 1 d . . . . .
C8 C 0.18339(9) 0.6433(3) 0.17918(10) 0.0338(4) Uani 1 1 d . . . . .
C9 C 0.16801(9) 0.8385(3) 0.22114(10) 0.0326(4) Uani 1 1 d . . . . .
C10 C 0.28218(9) 0.7414(3) 0.32462(10) 0.0355(4) Uani 1 1 d . . . . .
C11 C 0.29932(10) 0.5454(3) 0.28565(10) 0.0373(4) Uani 1 1 d . . . . .
H11 H 0.3443 0.4489 0.3091 0.045 Uiso 1 1 calc R U . . .
C12 C 0.10031(9) 0.9976(3) 0.18865(10) 0.0344(4) Uani 1 1 d . . . . .
C13 C 0.04414(10) 0.9931(4) 0.11519(11) 0.0408(4) Uani 1 1 d . . . . .
H13 H 0.0407 0.8771 0.0754 0.049 Uiso 1 1 calc R U . . .
C14 C -0.00687(10) 1.1897(4) 0.10957(11) 0.0445(5) Uani 1 1 d . . . . .
H14 H -0.0510 1.2321 0.0654 0.053 Uiso 1 1 calc R U . . .
C15 C 0.01862(10) 1.3084(4) 0.17916(11) 0.0440(5) Uani 1 1 d . . . . .
H15 H -0.0051 1.4493 0.1918 0.053 Uiso 1 1 calc R U . . .
C16 C 0.12394(11) 1.2776(4) 0.30737(11) 0.0455(5) Uani 1 1 d . . . . .
H16A H 0.0949 1.4109 0.3191 0.068 Uiso 1 1 calc R U . . .
H16B H 0.1724 1.3496 0.3147 0.068 Uiso 1 1 calc R U . . .
H16C H 0.1317 1.1289 0.3417 0.068 Uiso 1 1 calc R U . . .
C17 C 0.33245(9) 0.8094(4) 0.40521(10) 0.0373(4) Uani 1 1 d . . . . .
C20 C 0.42509(10) 0.9260(4) 0.55837(11) 0.0445(5) Uani 1 1 d . . . . .
C18 C 0.3247(3) 1.0410(11) 0.4385(4) 0.0454(12) Uani 0.5 1 d . U P A 1
H18 H 0.2878 1.1618 0.4081 0.054 Uiso 0.5 1 calc R U P A 1
C19 C 0.3691(3) 1.1005(11) 0.5141(4) 0.0465(12) Uani 0.5 1 d . U P A 1
H19 H 0.3619 1.2578 0.5359 0.056 Uiso 0.5 1 calc R U P A 1
C21 C 0.4305(2) 0.6872(8) 0.5303(2) 0.0441(8) Uani 0.5 1 d . U P A 1
H21 H 0.4649 0.5631 0.5628 0.053 Uiso 0.5 1 calc R U P A 1
C22 C 0.3860(2) 0.6260(8) 0.4547(2) 0.0420(8) Uani 0.5 1 d . U P A 1
H22 H 0.3908 0.4610 0.4351 0.050 Uiso 0.5 1 calc R U P A 1
C18' C 0.3089(3) 0.9572(10) 0.4487(3) 0.0406(10) Uani 0.5 1 d . U P A 2
H18' H 0.2596 1.0249 0.4269 0.049 Uiso 0.5 1 calc R U P A 2
C19' C 0.3552(3) 1.0118(10) 0.5243(4) 0.0405(10) Uani 0.5 1 d . U P A 2
H19' H 0.3364 1.1148 0.5532 0.049 Uiso 0.5 1 calc R U P A 2
C21' C 0.4547(2) 0.8004(9) 0.5106(2) 0.0500(9) Uani 0.5 1 d . U P A 2
H21' H 0.5061 0.7565 0.5308 0.060 Uiso 0.5 1 calc R U P A 2
C22' C 0.4084(2) 0.7437(9) 0.4353(2) 0.0495(9) Uani 0.5 1 d . U P A 2
H22' H 0.4279 0.6599 0.4036 0.059 Uiso 0.5 1 calc R U P A 2
C23 C 0.47123(13) 0.9784(5) 0.64120(13) 0.0589(6) Uani 1 1 d . . . . .
F1 F 0.5383(6) 0.8987(17) 0.6662(6) 0.098(2) Uani 0.5 1 d . U P B 1
F2 F 0.4377(4) 0.8671(9) 0.6840(4) 0.0916(17) Uani 0.6 1 d . U P B 1
F3 F 0.47334(18) 1.2269(8) 0.6583(2) 0.0746(10) Uani 0.6 1 d . U P B 1
F1' F 0.5308(7) 0.8141(15) 0.6727(6) 0.0815(19) Uani 0.5 1 d . U P B 2
F2' F 0.4377(6) 0.9773(15) 0.6849(6) 0.091(2) Uani 0.4 1 d . U P B 2
F3' F 0.5111(4) 1.2012(14) 0.6537(4) 0.118(2) Uani 0.4 1 d . U P B 2


_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
N1 C9 1.340(2) . ?
N1 C10 1.358(2) . ?
N2 C15 1.365(2) . ?
N2 C12 1.384(2) . ?
N2 C16 1.455(2) . ?
O1 C8 1.379(2) . ?
O1 C1 1.386(2) . ?
C1 C2 1.377(3) . ?
C1 C6 1.393(3) . ?
C2 C3 1.386(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.393(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.377(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.397(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.442(2) . ?
C7 C11 1.390(2) . ?
C7 C8 1.393(2) . ?
C8 C9 1.400(2) . ?
C9 C12 1.465(2) . ?
C10 C11 1.381(2) . ?
C10 C17 1.486(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.379(2) . ?
C13 C14 1.401(3) . ?
C13 H13 0.9500 . ?
C14 C15 1.359(3) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 C18' 1.349(6) . ?
C17 C18 1.392(6) . ?
C17 C22' 1.403(4) . ?
C17 C22 1.438(4) . ?
C20 C19' 1.330(6) . ?
C20 C21 1.366(5) . ?
C20 C19 1.401(6) . ?
C20 C21' 1.434(5) . ?
C20 C23 1.487(3) . ?
C18 C19 1.378(7) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C21 C22 1.380(5) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
C18' C19' 1.380(7) . ?
C18' H18' 0.9500 . ?
C19' H19' 0.9500 . ?
C21' C22' 1.378(6) . ?
C21' H21' 0.9500 . ?
C22' H22' 0.9500 . ?
C23 F2' 1.269(11) . ?
C23 F1 1.273(12) . ?
C23 F3 1.318(5) . ?
C23 F3' 1.356(7) . ?
C23 F1' 1.366(10) . ?
C23 F2 1.380(7) . ?

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 N1 C10 120.99(15) . . ?
C15 N2 C12 108.17(15) . . ?
C15 N2 C16 122.23(16) . . ?
C12 N2 C16 129.61(15) . . ?
C8 O1 C1 105.40(13) . . ?
C2 C1 O1 124.82(16) . . ?
C2 C1 C6 123.68(17) . . ?
O1 C1 C6 111.50(15) . . ?
C1 C2 C3 115.96(18) . . ?
C1 C2 H2 122.0 . . ?
C3 C2 H2 122.0 . . ?
C2 C3 C4 121.77(18) . . ?
C2 C3 H3 119.1 . . ?
C4 C3 H3 119.1 . . ?
C5 C4 C3 121.37(19) . . ?
C5 C4 H4 119.3 . . ?
C3 C4 H4 119.3 . . ?
C4 C5 C6 117.97(18) . . ?
C4 C5 H5 121.0 . . ?
C6 C5 H5 121.0 . . ?
C1 C6 C5 119.23(17) . . ?
C1 C6 C7 105.60(15) . . ?
C5 C6 C7 135.15(17) . . ?
C11 C7 C8 118.78(16) . . ?
C11 C7 C6 135.26(16) . . ?
C8 C7 C6 105.96(15) . . ?
O1 C8 C7 111.54(15) . . ?
O1 C8 C9 126.65(15) . . ?
C7 C8 C9 121.81(16) . . ?
N1 C9 C8 117.99(15) . . ?
N1 C9 C12 119.48(15) . . ?
C8 C9 C12 122.51(15) . . ?
N1 C10 C11 123.00(16) . . ?
N1 C10 C17 115.14(15) . . ?
C11 C10 C17 121.84(15) . . ?
C10 C11 C7 117.42(16) . . ?
C10 C11 H11 121.3 . . ?
C7 C11 H11 121.3 . . ?
C13 C12 N2 107.28(15) . . ?
C13 C12 C9 128.52(17) . . ?
N2 C12 C9 124.15(15) . . ?
C12 C13 C14 108.03(17) . . ?
C12 C13 H13 126.0 . . ?
C14 C13 H13 126.0 . . ?
C15 C14 C13 107.05(16) . . ?
C15 C14 H14 126.5 . . ?
C13 C14 H14 126.5 . . ?
C14 C15 N2 109.48(17) . . ?
C14 C15 H15 125.3 . . ?
N2 C15 H15 125.3 . . ?
N2 C16 H16A 109.5 . . ?
N2 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
N2 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C18' C17 C22' 118.0(3) . . ?
C18 C17 C22 116.9(3) . . ?
C18' C17 C10 121.6(3) . . ?
C18 C17 C10 121.7(3) . . ?
C22' C17 C10 120.1(2) . . ?
C22 C17 C10 121.0(2) . . ?
C21 C20 C19 120.8(3) . . ?
C19' C20 C21' 117.0(3) . . ?
C19' C20 C23 120.4(3) . . ?
C21 C20 C23 118.1(2) . . ?
C19 C20 C23 120.3(3) . . ?
C21' C20 C23 122.3(2) . . ?
C19 C18 C17 122.0(5) . . ?
C19 C18 H18 119.0 . . ?
C17 C18 H18 119.0 . . ?
C18 C19 C20 119.1(5) . . ?
C18 C19 H19 120.5 . . ?
C20 C19 H19 120.5 . . ?
C20 C21 C22 120.0(3) . . ?
C20 C21 H21 120.0 . . ?
C22 C21 H21 120.0 . . ?
C21 C22 C17 120.7(3) . . ?
C21 C22 H22 119.7 . . ?
C17 C22 H22 119.7 . . ?
C17 C18' C19' 121.2(4) . . ?
C17 C18' H18' 119.4 . . ?
C19' C18' H18' 119.4 . . ?
C20 C19' C18' 122.6(5) . . ?
C20 C19' H19' 118.7 . . ?
C18' C19' H19' 118.7 . . ?
C22' C21' C20 119.8(3) . . ?
C22' C21' H21' 120.1 . . ?
C20 C21' H21' 120.1 . . ?
C21' C22' C17 120.2(4) . . ?
C21' C22' H22' 119.9 . . ?
C17 C22' H22' 119.9 . . ?
F1 C23 F3 107.5(5) . . ?
F2' C23 F3' 108.3(6) . . ?
F2' C23 F1' 107.3(7) . . ?
F3' C23 F1' 96.8(5) . . ?
F1 C23 F2 109.1(6) . . ?
F3 C23 F2 103.1(4) . . ?
F2' C23 C20 116.8(5) . . ?
F1 C23 C20 114.6(6) . . ?
F3 C23 C20 112.6(2) . . ?
F3' C23 C20 113.0(3) . . ?
F1' C23 C20 112.7(5) . . ?
F2 C23 C20 109.3(3) . . ?

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
C8 O1 C1 C2 179.55(17) . . . . ?
C8 O1 C1 C6 0.30(18) . . . . ?
O1 C1 C2 C3 -178.40(16) . . . . ?
C6 C1 C2 C3 0.8(3) . . . . ?
C1 C2 C3 C4 0.7(3) . . . . ?
C2 C3 C4 C5 -1.5(3) . . . . ?
C3 C4 C5 C6 0.8(3) . . . . ?
C2 C1 C6 C5 -1.4(3) . . . . ?
O1 C1 C6 C5 177.83(14) . . . . ?
C2 C1 C6 C7 180.00(17) . . . . ?
O1 C1 C6 C7 -0.74(19) . . . . ?
C4 C5 C6 C1 0.6(3) . . . . ?
C4 C5 C6 C7 178.67(19) . . . . ?
C1 C6 C7 C11 -178.22(19) . . . . ?
C5 C6 C7 C11 3.6(4) . . . . ?
C1 C6 C7 C8 0.87(18) . . . . ?
C5 C6 C7 C8 -177.36(19) . . . . ?
C1 O1 C8 C7 0.29(18) . . . . ?
C1 O1 C8 C9 179.86(16) . . . . ?
C11 C7 C8 O1 178.54(14) . . . . ?
C6 C7 C8 O1 -0.73(19) . . . . ?
C11 C7 C8 C9 -1.1(3) . . . . ?
C6 C7 C8 C9 179.67(15) . . . . ?
C10 N1 C9 C8 0.0(2) . . . . ?
C10 N1 C9 C12 -178.86(15) . . . . ?
O1 C8 C9 N1 -178.66(15) . . . . ?
C7 C8 C9 N1 0.9(2) . . . . ?
O1 C8 C9 C12 0.1(3) . . . . ?
C7 C8 C9 C12 179.67(15) . . . . ?
C9 N1 C10 C11 -0.6(3) . . . . ?
C9 N1 C10 C17 -179.50(15) . . . . ?
N1 C10 C11 C7 0.4(3) . . . . ?
C17 C10 C11 C7 179.22(16) . . . . ?
C8 C7 C11 C10 0.4(2) . . . . ?
C6 C7 C11 C10 179.40(18) . . . . ?
C15 N2 C12 C13 -0.49(19) . . . . ?
C16 N2 C12 C13 179.14(17) . . . . ?
C15 N2 C12 C9 176.92(16) . . . . ?
C16 N2 C12 C9 -3.4(3) . . . . ?
N1 C9 C12 C13 176.33(17) . . . . ?
C8 C9 C12 C13 -2.4(3) . . . . ?
N1 C9 C12 N2 -0.5(2) . . . . ?
C8 C9 C12 N2 -179.29(15) . . . . ?
N2 C12 C13 C14 0.5(2) . . . . ?
C9 C12 C13 C14 -176.75(17) . . . . ?
C12 C13 C14 C15 -0.4(2) . . . . ?
C13 C14 C15 N2 0.0(2) . . . . ?
C12 N2 C15 C14 0.3(2) . . . . ?
C16 N2 C15 C14 -179.39(16) . . . . ?
N1 C10 C17 C18' 14.0(3) . . . . ?
C11 C10 C17 C18' -164.9(3) . . . . ?
N1 C10 C17 C18 -16.4(3) . . . . ?
C11 C10 C17 C18 164.8(3) . . . . ?
N1 C10 C17 C22' -159.1(3) . . . . ?
C11 C10 C17 C22' 22.0(3) . . . . ?
N1 C10 C17 C22 156.9(2) . . . . ?
C11 C10 C17 C22 -22.0(3) . . . . ?
C18' C17 C18 C19 79.3(11) . . . . ?
C22' C17 C18 C19 -36.3(6) . . . . ?
C22 C17 C18 C19 3.7(6) . . . . ?
C10 C17 C18 C19 177.2(4) . . . . ?
C17 C18 C19 C20 1.8(7) . . . . ?
C19' C20 C19 C18 -78.8(11) . . . . ?
C21 C20 C19 C18 -7.4(6) . . . . ?
C21' C20 C19 C18 33.7(6) . . . . ?
C23 C20 C19 C18 -176.8(4) . . . . ?
C19' C20 C21 C22 33.0(5) . . . . ?
C19 C20 C21 C22 7.3(6) . . . . ?
C21' C20 C21 C22 -75.5(5) . . . . ?
C23 C20 C21 C22 176.8(3) . . . . ?
C20 C21 C22 C17 -1.5(6) . . . . ?
C18' C17 C22 C21 -30.2(5) . . . . ?
C18 C17 C22 C21 -3.9(5) . . . . ?
C22' C17 C22 C21 82.3(5) . . . . ?
C10 C17 C22 C21 -177.5(3) . . . . ?
C18 C17 C18' C19' -84.0(11) . . . . ?
C22' C17 C18' C19' -9.1(6) . . . . ?
C22 C17 C18' C19' 30.6(5) . . . . ?
C10 C17 C18' C19' 177.7(3) . . . . ?
C21 C20 C19' C18' -33.8(5) . . . . ?
C19 C20 C19' C18' 86.1(12) . . . . ?
C21' C20 C19' C18' 7.9(6) . . . . ?
C23 C20 C19' C18' -176.7(3) . . . . ?
C17 C18' C19' C20 0.8(7) . . . . ?
C19' C20 C21' C22' -8.3(6) . . . . ?
C21 C20 C21' C22' 80.5(5) . . . . ?
C19 C20 C21' C22' -34.9(6) . . . . ?
C23 C20 C21' C22' 176.4(4) . . . . ?
C20 C21' C22' C17 0.3(7) . . . . ?
C18' C17 C22' C21' 8.4(6) . . . . ?
C18 C17 C22' C21' 34.7(6) . . . . ?
C22 C17 C22' C21' -75.3(5) . . . . ?
C10 C17 C22' C21' -178.3(4) . . . . ?
C19' C20 C23 F2' 35.6(5) . . . . ?
C21 C20 C23 F2' -104.3(5) . . . . ?
C19 C20 C23 F2' 65.3(5) . . . . ?
C21' C20 C23 F2' -149.2(5) . . . . ?
C19' C20 C23 F1 -176.4(5) . . . . ?
C21 C20 C23 F1 43.7(6) . . . . ?
C19 C20 C23 F1 -146.7(5) . . . . ?
C21' C20 C23 F1 -1.2(6) . . . . ?
C19' C20 C23 F3 -53.1(4) . . . . ?
C21 C20 C23 F3 166.9(3) . . . . ?
C19 C20 C23 F3 -23.5(4) . . . . ?
C21' C20 C23 F3 122.0(4) . . . . ?
C19' C20 C23 F3' -91.0(5) . . . . ?
C21 C20 C23 F3' 129.1(5) . . . . ?
C19 C20 C23 F3' -61.3(5) . . . . ?
C21' C20 C23 F3' 84.2(5) . . . . ?
C19' C20 C23 F1' 160.6(6) . . . . ?
C21 C20 C23 F1' 20.6(6) . . . . ?
C19 C20 C23 F1' -169.8(6) . . . . ?
C21' C20 C23 F1' -24.3(6) . . . . ?
C19' C20 C23 F2 60.8(4) . . . . ?
C21 C20 C23 F2 -79.1(4) . . . . ?
C19 C20 C23 F2 90.5(4) . . . . ?
C21' C20 C23 F2 -124.0(4) . . . . ?

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
C13 H13 O1 0.95 2.38 2.937(2) 116.9 .
C13 H13 O1 0.95 2.38 2.937(2) 116.9 .
C13 H13 O1 0.95 2.38 2.937(2) 116.9 .
C13 H13 O1 0.95 2.38 2.937(2) 116.9 .
C13 H13 O1 0.95 2.38 2.937(2) 116.9 .

_refine_diff_density_max         0.272
_refine_diff_density_min         -0.295
_refine_diff_density_rms         0.039

_shelxl_version_number           2013-4



####################################################################### 
# 
# 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_mo_dd19332_0m
_database_code_depnum_ccdc_archive 'CCDC 1971642'
loop_
_audit_author_name
_audit_author_address
'Jiuxi Chen'
;Wenzhou University
China
;
_audit_update_record             
;
2019-12-12 deposited with the CCDC.	2020-02-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H19 Cl N2 O'
_chemical_formula_weight         422.89

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'
Cl Cl 0.1484 0.1585 '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      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                   7.5249(7)
_cell_length_b                   12.0711(12)
_cell_length_c                   12.6412(13)
_cell_angle_alpha                109.203(3)
_cell_angle_beta                 106.952(3)
_cell_angle_gamma                98.580(3)
_cell_volume                     998.33(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    193(2)
_cell_measurement_reflns_used    7868
_cell_measurement_theta_min      5.682
_cell_measurement_theta_max      55.076

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.407
_exptl_crystal_F_000             440
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    0.215
_shelx_estimated_absorpt_T_min   0.962
_shelx_estimated_absorpt_T_max   0.973
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.4982
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      193(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            13828
_diffrn_reflns_av_unetI/netI     0.0418
_diffrn_reflns_av_R_equivalents  0.0484
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.841
_diffrn_reflns_theta_max         25.498
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3697
_reflns_number_gt                3127
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_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)+(0.0892P)²+0.2987P] 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     SHELXL
_refine_ls_extinction_coef       0.038(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3697
_refine_ls_number_parameters     283
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0585
_refine_ls_R_factor_gt           0.0500
_refine_ls_wR_factor_ref         0.1463
_refine_ls_wR_factor_gt          0.1362
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_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
Cl1 Cl 0.25897(9) 0.07849(5) 0.02450(5) 0.0545(2) Uani 1 1 d . . . . .
N1 N 0.8589(2) 0.71632(14) 0.58761(14) 0.0309(4) Uani 1 1 d . . . . .
N2 N 0.7311(2) 1.00063(14) 0.42814(15) 0.0358(4) Uani 1 1 d . . . . .
O1 O 0.48496(19) 0.60426(12) 0.28828(12) 0.0348(3) Uani 1 1 d . . . . .
C1 C 0.4128(3) 0.48055(17) 0.22040(17) 0.0313(4) Uani 1 1 d . . . . .
C2 C 0.2770(3) 0.42909(19) 0.10428(17) 0.0364(5) Uani 1 1 d . . . . .
H2 H 0.2190 0.4776 0.0663 0.044 Uiso 1 1 calc R U . . .
C3 C 0.2303(3) 0.30428(19) 0.04667(17) 0.0370(5) Uani 1 1 d . . . . .
H3 H 0.1395 0.2650 -0.0335 0.044 Uiso 1 1 calc R U . . .
C4 C 0.3151(3) 0.23502(18) 0.10518(18) 0.0361(5) Uani 1 1 d . . . . .
C5 C 0.4457(3) 0.28602(17) 0.22225(17) 0.0331(4) Uani 1 1 d . . . . .
H5 H 0.4993 0.2370 0.2612 0.040 Uiso 1 1 calc R U . . .
C6 C 0.4953(3) 0.41226(17) 0.28082(16) 0.0301(4) Uani 1 1 d . . . . .
C7 C 0.6316(3) 0.50150(17) 0.39662(16) 0.0292(4) Uani 1 1 d . . . . .
C8 C 0.6225(3) 0.61435(17) 0.39394(16) 0.0303(4) Uani 1 1 d . . . . .
C9 C 0.7425(3) 0.72371(17) 0.48794(16) 0.0301(4) Uani 1 1 d . . . . .
C10 C 0.8652(3) 0.60755(17) 0.59469(16) 0.0296(4) Uani 1 1 d . . . . .
C11 C 0.7568(3) 0.49661(17) 0.49958(16) 0.0305(4) Uani 1 1 d . . . . .
H11 H 0.7679 0.4211 0.5049 0.037 Uiso 1 1 calc R U . . .
C12 C 0.7466(3) 0.84471(17) 0.48735(17) 0.0310(4) Uani 1 1 d . . . . .
C13 C 0.7289(3) 0.88019(17) 0.39207(17) 0.0326(4) Uani 1 1 d . . . . .
C14 C 0.7521(3) 1.04654(17) 0.54811(18) 0.0340(4) Uani 1 1 d . . . . .
C15 C 0.7664(3) 0.95139(17) 0.58890(17) 0.0313(4) Uani 1 1 d . . . . .
C16 C 0.7926(3) 0.97596(18) 0.70983(18) 0.0355(4) Uani 1 1 d . . . . .
H16 H 0.8050 0.9142 0.7404 0.043 Uiso 1 1 calc R U . . .
C17 C 0.8001(3) 1.09132(19) 0.78351(19) 0.0414(5) Uani 1 1 d . . . . .
H17 H 0.8186 1.1088 0.8655 0.050 Uiso 1 1 calc R U . . .
C18 C 0.7809(3) 1.18318(19) 0.7399(2) 0.0450(5) Uani 1 1 d . . . . .
H18 H 0.7849 1.2614 0.7926 0.054 Uiso 1 1 calc R U . . .
C19 C 0.7563(3) 1.16222(18) 0.6218(2) 0.0411(5) Uani 1 1 d . . . . .
H19 H 0.7428 1.2244 0.5919 0.049 Uiso 1 1 calc R U . . .
C20 C 0.7206(3) 1.0726(2) 0.3553(2) 0.0454(5) Uani 1 1 d . . . . .
H20A H 0.8511 1.1184 0.3713 0.068 Uiso 1 1 calc R U . . .
H20B H 0.6439 1.1295 0.3757 0.068 Uiso 1 1 calc R U . . .
H20C H 0.6598 1.0183 0.2700 0.068 Uiso 1 1 calc R U . . .
C21 C 0.7232(3) 0.81218(19) 0.26856(18) 0.0407(5) Uani 1 1 d . . . . .
H21A H 0.5972 0.8015 0.2095 0.061 Uiso 1 1 calc R U . . .
H21B H 0.7436 0.7321 0.2615 0.061 Uiso 1 1 calc R U . . .
H21C H 0.8251 0.8582 0.2535 0.061 Uiso 1 1 calc R U . . .
C22 C 1.0002(3) 0.61467(17) 0.71158(16) 0.0302(4) Uani 1 1 d . . . . .
C23 C 1.0295(3) 0.51120(18) 0.73163(17) 0.0354(4) Uani 1 1 d . . . . .
H23 H 0.9611 0.4330 0.6697 0.042 Uiso 1 1 calc R U . . .
C24 C 1.1567(3) 0.5200(2) 0.84039(18) 0.0397(5) Uani 1 1 d . . . . .
H24 H 1.1741 0.4481 0.8525 0.048 Uiso 1 1 calc R U . . .
C25 C 1.2584(3) 0.6331(2) 0.93137(17) 0.0391(5) Uani 1 1 d . . . . .
H25 H 1.3462 0.6392 1.0057 0.047 Uiso 1 1 calc R U . . .
C26 C 1.2313(3) 0.73720(19) 0.91320(18) 0.0384(5) Uani 1 1 d . . . . .
H26 H 1.3008 0.8151 0.9753 0.046 Uiso 1 1 calc R U . . .
C27 C 1.1029(3) 0.72847(18) 0.80475(17) 0.0351(4) Uani 1 1 d . . . . .
H27 H 1.0846 0.8006 0.7936 0.042 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
Cl1 C4 1.741(2) . ?
N1 C9 1.348(2) . ?
N1 C10 1.352(2) . ?
N2 C13 1.369(2) . ?
N2 C14 1.383(3) . ?
N2 C20 1.453(3) . ?
O1 C1 1.380(2) . ?
O1 C8 1.385(2) . ?
C1 C2 1.386(3) . ?
C1 C6 1.392(3) . ?
C2 C3 1.376(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.394(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.381(3) . ?
C5 C6 1.392(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.453(3) . ?
C7 C8 1.385(3) . ?
C7 C11 1.392(2) . ?
C8 C9 1.399(3) . ?
C9 C12 1.459(3) . ?
C10 C11 1.395(3) . ?
C10 C22 1.496(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.384(3) . ?
C12 C15 1.439(3) . ?
C13 C21 1.490(3) . ?
C14 C19 1.390(3) . ?
C14 C15 1.411(3) . ?
C15 C16 1.404(3) . ?
C16 C17 1.379(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.399(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.380(3) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 0.9800 . ?
C22 C23 1.389(3) . ?
C22 C27 1.400(3) . ?
C23 C24 1.387(3) . ?
C23 H23 0.9500 . ?
C24 C25 1.384(3) . ?
C24 H24 0.9500 . ?
C25 C26 1.383(3) . ?
C25 H25 0.9500 . ?
C26 C27 1.388(3) . ?
C26 H26 0.9500 . ?
C27 H27 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
C9 N1 C10 121.42(16) . . ?
C13 N2 C14 109.35(15) . . ?
C13 N2 C20 126.44(18) . . ?
C14 N2 C20 124.18(17) . . ?
C1 O1 C8 104.81(14) . . ?
O1 C1 C2 124.36(17) . . ?
O1 C1 C6 112.29(16) . . ?
C2 C1 C6 123.33(18) . . ?
C3 C2 C1 116.74(18) . . ?
C3 C2 H2 121.6 . . ?
C1 C2 H2 121.6 . . ?
C2 C3 C4 120.48(18) . . ?
C2 C3 H3 119.8 . . ?
C4 C3 H3 119.8 . . ?
C5 C4 C3 122.73(19) . . ?
C5 C4 Cl1 119.15(16) . . ?
C3 C4 Cl1 118.09(15) . . ?
C4 C5 C6 117.19(18) . . ?
C4 C5 H5 121.4 . . ?
C6 C5 H5 121.4 . . ?
C5 C6 C1 119.47(17) . . ?
C5 C6 C7 135.33(17) . . ?
C1 C6 C7 105.07(16) . . ?
C8 C7 C11 118.84(17) . . ?
C8 C7 C6 105.72(16) . . ?
C11 C7 C6 135.44(18) . . ?
C7 C8 O1 112.03(16) . . ?
C7 C8 C9 122.49(17) . . ?
O1 C8 C9 125.47(17) . . ?
N1 C9 C8 117.23(17) . . ?
N1 C9 C12 117.83(16) . . ?
C8 C9 C12 124.91(17) . . ?
N1 C10 C11 122.73(17) . . ?
N1 C10 C22 114.99(16) . . ?
C11 C10 C22 122.27(17) . . ?
C7 C11 C10 117.06(17) . . ?
C7 C11 H11 121.5 . . ?
C10 C11 H11 121.5 . . ?
C13 C12 C15 106.54(17) . . ?
C13 C12 C9 128.17(18) . . ?
C15 C12 C9 125.27(17) . . ?
N2 C13 C12 109.56(17) . . ?
N2 C13 C21 119.73(17) . . ?
C12 C13 C21 130.53(18) . . ?
N2 C14 C19 129.86(18) . . ?
N2 C14 C15 107.55(16) . . ?
C19 C14 C15 122.59(19) . . ?
C16 C15 C14 118.56(18) . . ?
C16 C15 C12 134.48(18) . . ?
C14 C15 C12 106.95(17) . . ?
C17 C16 C15 118.86(19) . . ?
C17 C16 H16 120.6 . . ?
C15 C16 H16 120.6 . . ?
C16 C17 C18 121.4(2) . . ?
C16 C17 H17 119.3 . . ?
C18 C17 H17 119.3 . . ?
C19 C18 C17 121.21(19) . . ?
C19 C18 H18 119.4 . . ?
C17 C18 H18 119.4 . . ?
C18 C19 C14 117.39(19) . . ?
C18 C19 H19 121.3 . . ?
C14 C19 H19 121.3 . . ?
N2 C20 H20A 109.5 . . ?
N2 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
N2 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C13 C21 H21A 109.5 . . ?
C13 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C13 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C23 C22 C27 117.95(17) . . ?
C23 C22 C10 122.19(17) . . ?
C27 C22 C10 119.86(17) . . ?
C24 C23 C22 121.20(19) . . ?
C24 C23 H23 119.4 . . ?
C22 C23 H23 119.4 . . ?
C25 C24 C23 120.22(19) . . ?
C25 C24 H24 119.9 . . ?
C23 C24 H24 119.9 . . ?
C26 C25 C24 119.45(18) . . ?
C26 C25 H25 120.3 . . ?
C24 C25 H25 120.3 . . ?
C25 C26 C27 120.36(18) . . ?
C25 C26 H26 119.8 . . ?
C27 C26 H26 119.8 . . ?
C26 C27 C22 120.81(18) . . ?
C26 C27 H27 119.6 . . ?
C22 C27 H27 119.6 . . ?

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
C8 O1 C1 C2 -176.76(18) . . . . ?
C8 O1 C1 C6 1.9(2) . . . . ?
O1 C1 C2 C3 175.85(17) . . . . ?
C6 C1 C2 C3 -2.7(3) . . . . ?
C1 C2 C3 C4 1.1(3) . . . . ?
C2 C3 C4 C5 1.0(3) . . . . ?
C2 C3 C4 Cl1 -176.75(15) . . . . ?
C3 C4 C5 C6 -1.6(3) . . . . ?
Cl1 C4 C5 C6 176.12(14) . . . . ?
C4 C5 C6 C1 0.1(3) . . . . ?
C4 C5 C6 C7 -174.9(2) . . . . ?
O1 C1 C6 C5 -176.59(15) . . . . ?
C2 C1 C6 C5 2.1(3) . . . . ?
O1 C1 C6 C7 -0.2(2) . . . . ?
C2 C1 C6 C7 178.46(18) . . . . ?
C5 C6 C7 C8 173.9(2) . . . . ?
C1 C6 C7 C8 -1.6(2) . . . . ?
C5 C6 C7 C11 -6.2(4) . . . . ?
C1 C6 C7 C11 178.3(2) . . . . ?
C11 C7 C8 O1 -176.99(15) . . . . ?
C6 C7 C8 O1 2.9(2) . . . . ?
C11 C7 C8 C9 3.9(3) . . . . ?
C6 C7 C8 C9 -176.23(17) . . . . ?
C1 O1 C8 C7 -3.0(2) . . . . ?
C1 O1 C8 C9 176.10(17) . . . . ?
C10 N1 C9 C8 2.5(3) . . . . ?
C10 N1 C9 C12 -179.23(16) . . . . ?
C7 C8 C9 N1 -5.4(3) . . . . ?
O1 C8 C9 N1 175.62(16) . . . . ?
C7 C8 C9 C12 176.54(17) . . . . ?
O1 C8 C9 C12 -2.5(3) . . . . ?
C9 N1 C10 C11 1.7(3) . . . . ?
C9 N1 C10 C22 -179.47(15) . . . . ?
C8 C7 C11 C10 0.4(3) . . . . ?
C6 C7 C11 C10 -179.45(19) . . . . ?
N1 C10 C11 C7 -3.2(3) . . . . ?
C22 C10 C11 C7 178.06(16) . . . . ?
N1 C9 C12 C13 143.93(19) . . . . ?
C8 C9 C12 C13 -38.0(3) . . . . ?
N1 C9 C12 C15 -37.5(3) . . . . ?
C8 C9 C12 C15 140.6(2) . . . . ?
C14 N2 C13 C12 0.6(2) . . . . ?
C20 N2 C13 C12 178.43(18) . . . . ?
C14 N2 C13 C21 -175.19(17) . . . . ?
C20 N2 C13 C21 2.7(3) . . . . ?
C15 C12 C13 N2 -1.7(2) . . . . ?
C9 C12 C13 N2 177.06(17) . . . . ?
C15 C12 C13 C21 173.41(19) . . . . ?
C9 C12 C13 C21 -7.8(3) . . . . ?
C13 N2 C14 C19 -177.9(2) . . . . ?
C20 N2 C14 C19 4.1(3) . . . . ?
C13 N2 C14 C15 0.9(2) . . . . ?
C20 N2 C14 C15 -177.05(17) . . . . ?
N2 C14 C15 C16 178.82(17) . . . . ?
C19 C14 C15 C16 -2.3(3) . . . . ?
N2 C14 C15 C12 -1.9(2) . . . . ?
C19 C14 C15 C12 177.01(18) . . . . ?
C13 C12 C15 C16 -178.7(2) . . . . ?
C9 C12 C15 C16 2.5(3) . . . . ?
C13 C12 C15 C14 2.2(2) . . . . ?
C9 C12 C15 C14 -176.61(17) . . . . ?
C14 C15 C16 C17 1.1(3) . . . . ?
C12 C15 C16 C17 -177.9(2) . . . . ?
C15 C16 C17 C18 0.4(3) . . . . ?
C16 C17 C18 C19 -0.9(3) . . . . ?
C17 C18 C19 C14 -0.2(3) . . . . ?
N2 C14 C19 C18 -179.5(2) . . . . ?
C15 C14 C19 C18 1.8(3) . . . . ?
N1 C10 C22 C23 -177.30(17) . . . . ?
C11 C10 C22 C23 1.6(3) . . . . ?
N1 C10 C22 C27 2.3(2) . . . . ?
C11 C10 C22 C27 -178.88(17) . . . . ?
C27 C22 C23 C24 -0.1(3) . . . . ?
C10 C22 C23 C24 179.43(17) . . . . ?
C22 C23 C24 C25 -0.4(3) . . . . ?
C23 C24 C25 C26 0.4(3) . . . . ?
C24 C25 C26 C27 0.1(3) . . . . ?
C25 C26 C27 C22 -0.6(3) . . . . ?
C23 C22 C27 C26 0.6(3) . . . . ?
C10 C22 C27 C26 -178.96(17) . . . . ?

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
C21 H21B O1 0.98 2.47 2.984(2) 112.2 .
C20 H20A N1 0.98 2.52 3.476(3) 163.8 2_776
C21 H21B O1 0.98 2.47 2.984(2) 112.2 .
C20 H20A N1 0.98 2.52 3.476(3) 163.8 2_776

_refine_diff_density_max         0.337
_refine_diff_density_min         -0.328
_refine_diff_density_rms         0.065

_shelxl_version_number           2013-4



####################################################################### 
# 
# 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_mo_dd19333_0m
_database_code_depnum_ccdc_archive 'CCDC 1971643'
loop_
_audit_author_name
_audit_author_address
'Jiuxi Chen'
;Wenzhou University
China
;
_audit_update_record             
;
2019-12-12 deposited with the CCDC.	2020-02-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H14 F3 N O S'
_chemical_formula_weight         409.41

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

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   5.1204(6)
_cell_length_b                   15.2957(17)
_cell_length_c                   11.7653(14)
_cell_angle_alpha                90
_cell_angle_beta                 90.630(4)
_cell_angle_gamma                90
_cell_volume                     921.40(18)
_cell_formula_units_Z            2
_cell_measurement_temperature    193(2)
_cell_measurement_reflns_used    9876
_cell_measurement_theta_min      4.369
_cell_measurement_theta_max      54.475

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.476
_exptl_crystal_F_000             420
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.170
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.220
_shelx_estimated_absorpt_T_min   0.964
_shelx_estimated_absorpt_T_max   0.978
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5446
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      193(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            15773
_diffrn_reflns_av_unetI/netI     0.0505
_diffrn_reflns_av_R_equivalents  0.0668
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.663
_diffrn_reflns_theta_max         25.990
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             3614
_reflns_number_gt                3263
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.922
_reflns_Friedel_fraction_max     0.996
_reflns_Friedel_fraction_full    0.996

_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-2013 (Sheldrick, 2013)'
_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)+(0.0693P)²+0.6637P] 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_abs_structure_details 
; 
 Flack x determined using 1382 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   0.04(4)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         3614
_refine_ls_number_parameters     290
_refine_ls_number_restraints     37
_refine_ls_R_factor_all          0.0630
_refine_ls_R_factor_gt           0.0567
_refine_ls_wR_factor_ref         0.1513
_refine_ls_wR_factor_gt          0.1453
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.076
_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
S1 S 0.8514(3) 0.48961(9) 0.37915(12) 0.0456(4) Uani 1 1 d . . . . .
F1 F 1.058(3) 0.2534(8) 1.0148(12) 0.090(3) Uani 0.6 1 d . U P A 1
F2 F 0.752(2) 0.1734(6) 0.9617(8) 0.090(3) Uani 0.6 1 d . U P A 1
F3 F 0.692(3) 0.2555(13) 1.1046(18) 0.087(4) Uani 0.5 1 d . U P A 1
F1' F 1.023(5) 0.2194(12) 0.992(2) 0.094(4) Uani 0.4 1 d . U P A 2
F2' F 0.618(4) 0.1836(11) 1.0036(15) 0.100(4) Uani 0.4 1 d . U P A 2
F3' F 0.782(4) 0.2767(13) 1.1144(18) 0.083(4) Uani 0.5 1 d . U P A 2
O1 O 0.1759(7) 0.6889(2) 0.4561(3) 0.0405(8) Uani 1 1 d . . . . .
N1 N 0.5565(9) 0.5159(3) 0.5884(4) 0.0396(10) Uani 1 1 d . . . . .
C1 C -0.0165(10) 0.7298(4) 0.5151(5) 0.0403(12) Uani 1 1 d . . . . .
C2 C -0.1747(11) 0.7941(4) 0.4726(5) 0.0469(13) Uani 1 1 d . . . . .
H2 H -0.1567 0.8156 0.3974 0.056 Uiso 1 1 calc R U . . .
C3 C -0.3614(11) 0.8258(4) 0.5448(6) 0.0506(14) Uani 1 1 d . . . . .
H3 H -0.4774 0.8701 0.5187 0.061 Uiso 1 1 calc R U . . .
C4 C -0.3844(11) 0.7946(4) 0.6552(6) 0.0489(14) Uani 1 1 d . . . . .
H4 H -0.5127 0.8190 0.7036 0.059 Uiso 1 1 calc R U . . .
C5 C -0.2242(10) 0.7287(4) 0.6961(5) 0.0434(12) Uani 1 1 d . . . . .
H5 H -0.2433 0.7066 0.7710 0.052 Uiso 1 1 calc R U . . .
C6 C -0.0376(11) 0.6965(3) 0.6253(5) 0.0400(11) Uani 1 1 d . . . . .
C7 C 0.1578(10) 0.6293(4) 0.6341(4) 0.0378(11) Uani 1 1 d . . . . .
C8 C 0.2817(10) 0.6288(3) 0.5293(4) 0.0362(11) Uani 1 1 d . . . . .
C9 C 0.4802(10) 0.5715(3) 0.5060(5) 0.0364(11) Uani 1 1 d . . . . .
C10 C 0.4410(11) 0.5157(3) 0.6902(5) 0.0397(12) Uani 1 1 d . . . . .
C11 C 0.2422(10) 0.5718(4) 0.7165(4) 0.0406(12) Uani 1 1 d . . . . .
H11 H 0.1648 0.5710 0.7895 0.049 Uiso 1 1 calc R U . . .
C12 C 0.6156(11) 0.5667(3) 0.3975(4) 0.0404(12) Uani 1 1 d . . . . .
C13 C 0.5801(13) 0.6154(4) 0.3020(5) 0.0536(15) Uani 1 1 d . . . . .
H13 H 0.4573 0.6617 0.2956 0.064 Uiso 1 1 calc R U . . .
C14 C 0.7461(14) 0.5893(5) 0.2135(5) 0.0599(17) Uani 1 1 d . . . . .
H14 H 0.7476 0.6167 0.1411 0.072 Uiso 1 1 calc R U . . .
C15 C 0.9012(12) 0.5221(4) 0.2413(5) 0.0490(14) Uani 1 1 d . . . . .
C16 C 1.0944(14) 0.4776(5) 0.1692(6) 0.0682(19) Uani 1 1 d . . . . .
H16A H 1.0457 0.4160 0.1604 0.102 Uiso 1 1 calc R U . . .
H16B H 1.2677 0.4816 0.2049 0.102 Uiso 1 1 calc R U . . .
H16C H 1.0978 0.5057 0.0943 0.102 Uiso 1 1 calc R U . . .
C17 C 0.5390(11) 0.4498(4) 0.7729(5) 0.0430(12) Uani 1 1 d . . . . .
C18 C 0.7040(16) 0.3857(5) 0.7408(6) 0.071(2) Uani 1 1 d . . . . .
H18 H 0.7663 0.3850 0.6650 0.085 Uiso 1 1 calc R U . . .
C19 C 0.7842(16) 0.3212(6) 0.8152(6) 0.076(2) Uani 1 1 d . . . . .
H19 H 0.8944 0.2756 0.7890 0.091 Uiso 1 1 calc R U . . .
C20 C 0.7091(12) 0.3217(4) 0.9242(5) 0.0501(14) Uani 1 1 d . . . . .
C21 C 0.5543(18) 0.3867(6) 0.9606(7) 0.090(3) Uani 1 1 d . . . . .
H21 H 0.5022 0.3885 1.0378 0.108 Uiso 1 1 calc R U . . .
C22 C 0.471(2) 0.4508(7) 0.8857(6) 0.095(3) Uani 1 1 d . . . . .
H22 H 0.3632 0.4968 0.9128 0.114 Uiso 1 1 calc R U . . .
C23 C 0.7935(16) 0.2517(5) 1.0034(6) 0.0649(18) 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
S1 C12 1.703(6) . ?
S1 C15 1.718(6) . ?
F1 C23 1.358(17) . ?
F2 C23 1.311(12) . ?
F3 C23 1.31(2) . ?
F1' C23 1.28(3) . ?
F2' C23 1.376(19) . ?
F3' C23 1.36(2) . ?
O1 C1 1.364(6) . ?
O1 C8 1.368(6) . ?
N1 C10 1.342(7) . ?
N1 C9 1.345(7) . ?
C1 C2 1.365(8) . ?
C1 C6 1.399(8) . ?
C2 C3 1.375(9) . ?
C2 H2 0.9500 . ?
C3 C4 1.391(9) . ?
C3 H3 0.9500 . ?
C4 C5 1.382(8) . ?
C4 H4 0.9500 . ?
C5 C6 1.366(8) . ?
C5 H5 0.9500 . ?
C6 C7 1.437(8) . ?
C7 C11 1.375(8) . ?
C7 C8 1.393(7) . ?
C8 C9 1.371(7) . ?
C9 C12 1.461(7) . ?
C10 C11 1.369(8) . ?
C10 C17 1.485(7) . ?
C11 H11 0.9500 . ?
C12 C13 1.358(8) . ?
C13 C14 1.409(9) . ?
C13 H13 0.9500 . ?
C14 C15 1.336(9) . ?
C14 H14 0.9500 . ?
C15 C16 1.476(9) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 C18 1.350(8) . ?
C17 C22 1.376(9) . ?
C18 C19 1.379(10) . ?
C18 H18 0.9500 . ?
C19 C20 1.342(9) . ?
C19 H19 0.9500 . ?
C20 C21 1.344(9) . ?
C20 C23 1.481(9) . ?
C21 C22 1.384(10) . ?
C21 H21 0.9500 . ?
C22 H22 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
C12 S1 C15 91.8(3) . . ?
C1 O1 C8 105.7(4) . . ?
C10 N1 C9 121.2(4) . . ?
O1 C1 C2 125.0(5) . . ?
O1 C1 C6 111.6(5) . . ?
C2 C1 C6 123.4(5) . . ?
C1 C2 C3 116.3(6) . . ?
C1 C2 H2 121.9 . . ?
C3 C2 H2 121.9 . . ?
C2 C3 C4 121.5(6) . . ?
C2 C3 H3 119.2 . . ?
C4 C3 H3 119.2 . . ?
C5 C4 C3 121.3(6) . . ?
C5 C4 H4 119.4 . . ?
C3 C4 H4 119.4 . . ?
C6 C5 C4 117.9(6) . . ?
C6 C5 H5 121.1 . . ?
C4 C5 H5 121.1 . . ?
C5 C6 C1 119.7(5) . . ?
C5 C6 C7 134.9(5) . . ?
C1 C6 C7 105.5(5) . . ?
C11 C7 C8 118.5(5) . . ?
C11 C7 C6 136.1(5) . . ?
C8 C7 C6 105.3(5) . . ?
O1 C8 C9 126.3(5) . . ?
O1 C8 C7 111.9(4) . . ?
C9 C8 C7 121.8(5) . . ?
N1 C9 C8 118.0(5) . . ?
N1 C9 C12 117.4(5) . . ?
C8 C9 C12 124.5(5) . . ?
N1 C10 C11 122.4(5) . . ?
N1 C10 C17 115.9(4) . . ?
C11 C10 C17 121.7(5) . . ?
C10 C11 C7 118.0(5) . . ?
C10 C11 H11 121.0 . . ?
C7 C11 H11 121.0 . . ?
C13 C12 C9 129.4(5) . . ?
C13 C12 S1 111.3(4) . . ?
C9 C12 S1 119.3(4) . . ?
C12 C13 C14 112.3(6) . . ?
C12 C13 H13 123.9 . . ?
C14 C13 H13 123.9 . . ?
C15 C14 C13 113.5(6) . . ?
C15 C14 H14 123.2 . . ?
C13 C14 H14 123.2 . . ?
C14 C15 C16 127.9(6) . . ?
C14 C15 S1 111.0(5) . . ?
C16 C15 S1 121.1(5) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C18 C17 C22 116.4(6) . . ?
C18 C17 C10 121.2(5) . . ?
C22 C17 C10 122.4(5) . . ?
C17 C18 C19 121.6(6) . . ?
C17 C18 H18 119.2 . . ?
C19 C18 H18 119.2 . . ?
C20 C19 C18 121.0(6) . . ?
C20 C19 H19 119.5 . . ?
C18 C19 H19 119.5 . . ?
C19 C20 C21 119.0(6) . . ?
C19 C20 C23 120.8(6) . . ?
C21 C20 C23 120.2(6) . . ?
C20 C21 C22 120.1(7) . . ?
C20 C21 H21 120.0 . . ?
C22 C21 H21 120.0 . . ?
C17 C22 C21 121.7(7) . . ?
C17 C22 H22 119.1 . . ?
C21 C22 H22 119.1 . . ?
F3 C23 F2 108.5(11) . . ?
F3 C23 F1 108.4(12) . . ?
F2 C23 F1 102.1(9) . . ?
F1' C23 F3' 105.1(14) . . ?
F1' C23 F2' 107.8(13) . . ?
F3' C23 F2' 100.2(12) . . ?
F1' C23 C20 118.1(12) . . ?
F3 C23 C20 115.2(11) . . ?
F2 C23 C20 112.4(7) . . ?
F1 C23 C20 109.4(8) . . ?
F3' C23 C20 112.7(10) . . ?
F2' C23 C20 111.3(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
C8 O1 C1 C2 -179.1(5) . . . . ?
C8 O1 C1 C6 -0.4(6) . . . . ?
O1 C1 C2 C3 178.6(5) . . . . ?
C6 C1 C2 C3 0.1(8) . . . . ?
C1 C2 C3 C4 0.7(9) . . . . ?
C2 C3 C4 C5 -1.6(9) . . . . ?
C3 C4 C5 C6 1.5(8) . . . . ?
C4 C5 C6 C1 -0.7(8) . . . . ?
C4 C5 C6 C7 -178.7(6) . . . . ?
O1 C1 C6 C5 -178.7(5) . . . . ?
C2 C1 C6 C5 -0.1(8) . . . . ?
O1 C1 C6 C7 -0.2(6) . . . . ?
C2 C1 C6 C7 178.4(5) . . . . ?
C5 C6 C7 C11 -2.0(11) . . . . ?
C1 C6 C7 C11 179.9(6) . . . . ?
C5 C6 C7 C8 178.9(6) . . . . ?
C1 C6 C7 C8 0.8(6) . . . . ?
C1 O1 C8 C9 179.1(5) . . . . ?
C1 O1 C8 C7 1.0(6) . . . . ?
C11 C7 C8 O1 179.6(5) . . . . ?
C6 C7 C8 O1 -1.1(6) . . . . ?
C11 C7 C8 C9 1.4(8) . . . . ?
C6 C7 C8 C9 -179.3(5) . . . . ?
C10 N1 C9 C8 0.6(7) . . . . ?
C10 N1 C9 C12 -179.6(5) . . . . ?
O1 C8 C9 N1 -179.0(5) . . . . ?
C7 C8 C9 N1 -1.0(7) . . . . ?
O1 C8 C9 C12 1.2(8) . . . . ?
C7 C8 C9 C12 179.1(5) . . . . ?
C9 N1 C10 C11 -0.5(8) . . . . ?
C9 N1 C10 C17 178.6(5) . . . . ?
N1 C10 C11 C7 0.8(8) . . . . ?
C17 C10 C11 C7 -178.2(5) . . . . ?
C8 C7 C11 C10 -1.3(8) . . . . ?
C6 C7 C11 C10 179.7(6) . . . . ?
N1 C9 C12 C13 -179.0(6) . . . . ?
C8 C9 C12 C13 0.8(9) . . . . ?
N1 C9 C12 S1 2.4(6) . . . . ?
C8 C9 C12 S1 -177.8(4) . . . . ?
C15 S1 C12 C13 -0.5(5) . . . . ?
C15 S1 C12 C9 178.3(4) . . . . ?
C9 C12 C13 C14 -178.6(6) . . . . ?
S1 C12 C13 C14 0.1(7) . . . . ?
C12 C13 C14 C15 0.5(9) . . . . ?
C13 C14 C15 C16 178.9(7) . . . . ?
C13 C14 C15 S1 -0.9(8) . . . . ?
C12 S1 C15 C14 0.8(5) . . . . ?
C12 S1 C15 C16 -179.0(5) . . . . ?
N1 C10 C17 C18 -10.0(8) . . . . ?
C11 C10 C17 C18 169.1(7) . . . . ?
N1 C10 C17 C22 169.2(8) . . . . ?
C11 C10 C17 C22 -11.7(10) . . . . ?
C22 C17 C18 C19 4.5(13) . . . . ?
C10 C17 C18 C19 -176.2(7) . . . . ?
C17 C18 C19 C20 -2.7(14) . . . . ?
C18 C19 C20 C21 -0.3(13) . . . . ?
C18 C19 C20 C23 179.3(8) . . . . ?
C19 C20 C21 C22 1.2(14) . . . . ?
C23 C20 C21 C22 -178.5(9) . . . . ?
C18 C17 C22 C21 -3.7(15) . . . . ?
C10 C17 C22 C21 177.1(9) . . . . ?
C20 C21 C22 C17 0.8(17) . . . . ?
C19 C20 C23 F1' 35.1(15) . . . . ?
C21 C20 C23 F1' -145.2(13) . . . . ?
C19 C20 C23 F3 -174.9(11) . . . . ?
C21 C20 C23 F3 4.8(14) . . . . ?
C19 C20 C23 F2 -50.0(12) . . . . ?
C21 C20 C23 F2 129.7(10) . . . . ?
C19 C20 C23 F1 62.7(11) . . . . ?
C21 C20 C23 F1 -117.6(10) . . . . ?
C19 C20 C23 F3' 158.0(10) . . . . ?
C21 C20 C23 F3' -22.3(13) . . . . ?
C19 C20 C23 F2' -90.4(12) . . . . ?
C21 C20 C23 F2' 89.3(12) . . . . ?

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
C16 H16A F3' 0.98 2.58 3.519(19) 161.7 1_554
C14 H14 F1' 0.95 2.52 3.35(2) 147.2 2_756
C13 H13 O1 0.95 2.42 2.986(7) 117.7 .
C13 H13 O1 0.95 2.42 2.986(7) 117.7 .
C14 H14 F1' 0.95 2.52 3.35(2) 147.2 2_756
C16 H16A F3' 0.98 2.58 3.519(19) 161.7 1_554

_refine_diff_density_max         0.357
_refine_diff_density_min         -0.260
_refine_diff_density_rms         0.058

_shelxl_version_number           2013-4



####################################################################### 
# 
# 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_mo_dd19331_0m
_database_code_depnum_ccdc_archive 'CCDC 1971640'
loop_
_audit_author_name
_audit_author_address
'Jiuxi Chen'
;Wenzhou University
China
;
_audit_update_record             
;
2019-12-12 deposited with the CCDC.	2020-02-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C23 H14 F3 N O2'
_chemical_formula_weight         393.35

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      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                   19.5929(10)
_cell_length_b                   4.9462(2)
_cell_length_c                   20.1844(9)
_cell_angle_alpha                90
_cell_angle_beta                 116.132(2)
_cell_angle_gamma                90
_cell_volume                     1756.13(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    193(2)
_cell_measurement_reflns_used    5961
_cell_measurement_theta_min      4.496
_cell_measurement_theta_max      53.557

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.488
_exptl_crystal_F_000             808
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.120
_exptl_absorpt_coefficient_mu    0.117
_shelx_estimated_absorpt_T_min   0.979
_shelx_estimated_absorpt_T_max   0.986
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6659
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      193(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            19900
_diffrn_reflns_av_unetI/netI     0.0387
_diffrn_reflns_av_R_equivalents  0.0615
_diffrn_reflns_limit_h_min       -23
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -5
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.316
_diffrn_reflns_theta_max         25.499
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             3241
_reflns_number_gt                2508
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_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)+(0.0878P)²+2.1914P] 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     SHELXL
_refine_ls_extinction_coef       0.018(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3241
_refine_ls_number_parameters     291
_refine_ls_number_restraints     48
_refine_ls_R_factor_all          0.0833
_refine_ls_R_factor_gt           0.0644
_refine_ls_wR_factor_ref         0.1831
_refine_ls_wR_factor_gt          0.1645
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_restrained_S_all      1.156
_refine_ls_shift/su_max          0.004
_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 0.5594(3) 1.0372(15) 0.9745(3) 0.0665(16) Uani 0.5 1 d . U P A 1
F2 F 0.5090(4) 0.6510(13) 0.9388(4) 0.0835(16) Uani 0.5 1 d . U P A 1
F3 F 0.4583(2) 1.0129(11) 0.8756(2) 0.0856(13) Uani 0.6 1 d . U P A 1
F1' F 0.5672(4) 0.797(2) 0.9898(4) 0.1143(17) Uani 0.5 1 d . U P A 2
F2' F 0.4742(4) 0.718(2) 0.9018(4) 0.0978(18) Uani 0.5 1 d . U P A 2
F3' F 0.5278(6) 1.116(2) 0.9394(6) 0.103(2) Uani 0.4 1 d . U P A 2
O1 O 0.86196(10) 0.6936(4) 0.67374(9) 0.0318(5) Uani 1 1 d . . . . .
O2 O 0.86619(10) 0.1653(4) 0.85009(9) 0.0300(5) Uani 1 1 d . . . . .
N1 N 0.76448(12) 0.5666(4) 0.78918(12) 0.0309(5) Uani 1 1 d . . . . .
C1 C 0.83521(15) 0.8944(5) 0.62008(14) 0.0315(6) Uani 1 1 d . . . . .
C2 C 0.86790(17) 0.9632(6) 0.57430(15) 0.0375(7) Uani 1 1 d . . . . .
H2 H 0.9120 0.8742 0.5769 0.045 Uiso 1 1 calc R U . . .
C3 C 0.83293(17) 1.1692(6) 0.52429(16) 0.0412(7) Uani 1 1 d . . . . .
H3 H 0.8531 1.2213 0.4912 0.049 Uiso 1 1 calc R U . . .
C4 C 0.76912(18) 1.3017(6) 0.52130(15) 0.0423(7) Uani 1 1 d . . . . .
H4 H 0.7470 1.4436 0.4866 0.051 Uiso 1 1 calc R U . . .
C5 C 0.73723(16) 1.2312(6) 0.56779(15) 0.0372(7) Uani 1 1 d . . . . .
H5 H 0.6936 1.3226 0.5656 0.045 Uiso 1 1 calc R U . . .
C6 C 0.77094(14) 1.0215(5) 0.61815(14) 0.0314(6) Uani 1 1 d . . . . .
C7 C 0.75631(14) 0.8912(5) 0.67466(14) 0.0295(6) Uani 1 1 d . . . . .
C8 C 0.81228(14) 0.6955(5) 0.70577(13) 0.0284(6) Uani 1 1 d . . . . .
C9 C 0.81575(14) 0.5299(5) 0.76283(13) 0.0282(6) Uani 1 1 d . . . . .
C10 C 0.71070(14) 0.7603(5) 0.76117(14) 0.0310(6) Uani 1 1 d . . . . .
C11 C 0.70338(15) 0.9251(6) 0.70261(15) 0.0331(6) Uani 1 1 d . . . . .
H11 H 0.6639 1.0554 0.6825 0.040 Uiso 1 1 calc R U . . .
C12 C 0.87333(14) 0.3211(5) 0.79706(13) 0.0285(6) Uani 1 1 d . . . . .
C13 C 0.93538(15) 0.2421(5) 0.78904(14) 0.0320(6) Uani 1 1 d . . . . .
H13 H 0.9532 0.3165 0.7562 0.038 Uiso 1 1 calc R U . . .
C14 C 0.96867(15) 0.0260(6) 0.83944(14) 0.0337(6) Uani 1 1 d . . . . .
H14 H 1.0132 -0.0716 0.8467 0.040 Uiso 1 1 calc R U . . .
C15 C 0.92542(14) -0.0146(5) 0.87491(14) 0.0308(6) Uani 1 1 d . . . . .
C16 C 0.92793(17) -0.2073(6) 0.93212(15) 0.0383(7) Uani 1 1 d . . . . .
H16A H 0.9370 -0.1082 0.9773 0.057 Uiso 1 1 calc R U . . .
H16B H 0.9691 -0.3376 0.9426 0.057 Uiso 1 1 calc R U . . .
H16C H 0.8794 -0.3037 0.9143 0.057 Uiso 1 1 calc R U . . .
C17 C 0.66096(15) 0.7900(6) 0.79904(15) 0.0341(6) Uani 1 1 d . . . . .
C18 C 0.6707(2) 0.6259(8) 0.85723(19) 0.0552(9) Uani 1 1 d . . . . .
H18 H 0.7087 0.4897 0.8723 0.066 Uiso 1 1 calc R U . . .
C19 C 0.6261(2) 0.6542(8) 0.8948(2) 0.0593(10) Uani 1 1 d . . . . .
H19 H 0.6338 0.5370 0.9347 0.071 Uiso 1 1 calc R U . . .
C20 C 0.57174(17) 0.8487(7) 0.87441(18) 0.0454(8) Uani 1 1 d . . . . .
C21 C 0.5615(2) 1.0163(8) 0.8168(2) 0.0695(12) Uani 1 1 d . . . . .
H21 H 0.5240 1.1543 0.8026 0.083 Uiso 1 1 calc R U . . .
C22 C 0.6050(2) 0.9865(8) 0.7792(2) 0.0641(11) Uani 1 1 d . . . . .
H22 H 0.5965 1.1030 0.7389 0.077 Uiso 1 1 calc R U . . .
C23 C 0.5252(2) 0.8845(8) 0.9152(2) 0.0583(10) 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
F1 C23 1.321(6) . ?
F2 C23 1.339(7) . ?
F3 C23 1.355(5) . ?
F1' C23 1.428(8) . ?
F2' C23 1.228(8) . ?
F3' C23 1.237(10) . ?
O1 C8 1.386(3) . ?
O1 C1 1.391(3) . ?
O2 C15 1.370(3) . ?
O2 C12 1.375(3) . ?
N1 C9 1.340(3) . ?
N1 C10 1.350(3) . ?
C1 C2 1.379(4) . ?
C1 C6 1.393(4) . ?
C2 C3 1.385(4) . ?
C2 H2 0.9500 . ?
C3 C4 1.389(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.382(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.398(4) . ?
C5 H5 0.9500 . ?
C6 C7 1.444(4) . ?
C7 C8 1.388(4) . ?
C7 C11 1.392(4) . ?
C8 C9 1.390(4) . ?
C9 C12 1.459(4) . ?
C10 C11 1.390(4) . ?
C10 C17 1.487(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.353(4) . ?
C13 C14 1.421(4) . ?
C13 H13 0.9500 . ?
C14 C15 1.344(4) . ?
C14 H14 0.9500 . ?
C15 C16 1.481(4) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 C18 1.370(4) . ?
C17 C22 1.386(4) . ?
C18 C19 1.392(4) . ?
C18 H18 0.9500 . ?
C19 C20 1.358(5) . ?
C19 H19 0.9500 . ?
C20 C21 1.369(5) . ?
C20 C23 1.485(4) . ?
C21 C22 1.376(5) . ?
C21 H21 0.9500 . ?
C22 H22 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
C8 O1 C1 104.91(19) . . ?
C15 O2 C12 106.77(19) . . ?
C9 N1 C10 120.9(2) . . ?
C2 C1 O1 124.8(2) . . ?
C2 C1 C6 123.4(3) . . ?
O1 C1 C6 111.7(2) . . ?
C1 C2 C3 116.3(3) . . ?
C1 C2 H2 121.8 . . ?
C3 C2 H2 121.8 . . ?
C2 C3 C4 121.7(3) . . ?
C2 C3 H3 119.1 . . ?
C4 C3 H3 119.1 . . ?
C5 C4 C3 121.3(3) . . ?
C5 C4 H4 119.4 . . ?
C3 C4 H4 119.4 . . ?
C4 C5 C6 118.1(3) . . ?
C4 C5 H5 120.9 . . ?
C6 C5 H5 120.9 . . ?
C1 C6 C5 119.2(2) . . ?
C1 C6 C7 105.5(2) . . ?
C5 C6 C7 135.3(3) . . ?
C8 C7 C11 118.8(2) . . ?
C8 C7 C6 106.0(2) . . ?
C11 C7 C6 135.1(2) . . ?
O1 C8 C7 111.8(2) . . ?
O1 C8 C9 126.5(2) . . ?
C7 C8 C9 121.8(2) . . ?
N1 C9 C8 118.5(2) . . ?
N1 C9 C12 117.8(2) . . ?
C8 C9 C12 123.7(2) . . ?
N1 C10 C11 122.8(2) . . ?
N1 C10 C17 115.0(2) . . ?
C11 C10 C17 122.2(2) . . ?
C10 C11 C7 117.2(2) . . ?
C10 C11 H11 121.4 . . ?
C7 C11 H11 121.4 . . ?
C13 C12 O2 109.6(2) . . ?
C13 C12 C9 134.1(2) . . ?
O2 C12 C9 116.3(2) . . ?
C12 C13 C14 106.6(2) . . ?
C12 C13 H13 126.7 . . ?
C14 C13 H13 126.7 . . ?
C15 C14 C13 107.2(2) . . ?
C15 C14 H14 126.4 . . ?
C13 C14 H14 126.4 . . ?
C14 C15 O2 109.8(2) . . ?
C14 C15 C16 134.4(3) . . ?
O2 C15 C16 115.8(2) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C18 C17 C22 117.2(3) . . ?
C18 C17 C10 120.5(3) . . ?
C22 C17 C10 122.4(3) . . ?
C17 C18 C19 121.6(3) . . ?
C17 C18 H18 119.2 . . ?
C19 C18 H18 119.2 . . ?
C20 C19 C18 120.2(3) . . ?
C20 C19 H19 119.9 . . ?
C18 C19 H19 119.9 . . ?
C19 C20 C21 119.2(3) . . ?
C19 C20 C23 120.6(3) . . ?
C21 C20 C23 120.2(3) . . ?
C20 C21 C22 120.6(3) . . ?
C20 C21 H21 119.7 . . ?
C22 C21 H21 119.7 . . ?
C21 C22 C17 121.3(3) . . ?
C21 C22 H22 119.4 . . ?
C17 C22 H22 119.4 . . ?
F2' C23 F3' 126.6(6) . . ?
F1 C23 F2 106.0(5) . . ?
F1 C23 F3 103.9(4) . . ?
F2 C23 F3 107.2(5) . . ?
F2' C23 F1' 93.8(6) . . ?
F3' C23 F1' 87.7(6) . . ?
F2' C23 C20 115.8(4) . . ?
F3' C23 C20 113.6(5) . . ?
F1 C23 C20 112.4(3) . . ?
F2 C23 C20 113.1(4) . . ?
F3 C23 C20 113.6(3) . . ?
F1' C23 C20 109.9(4) . . ?

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
C8 O1 C1 C2 179.9(3) . . . . ?
C8 O1 C1 C6 0.4(3) . . . . ?
O1 C1 C2 C3 -179.9(2) . . . . ?
C6 C1 C2 C3 -0.4(4) . . . . ?
C1 C2 C3 C4 1.0(4) . . . . ?
C2 C3 C4 C5 -0.7(5) . . . . ?
C3 C4 C5 C6 -0.1(4) . . . . ?
C2 C1 C6 C5 -0.3(4) . . . . ?
O1 C1 C6 C5 179.2(2) . . . . ?
C2 C1 C6 C7 -179.5(3) . . . . ?
O1 C1 C6 C7 0.0(3) . . . . ?
C4 C5 C6 C1 0.6(4) . . . . ?
C4 C5 C6 C7 179.5(3) . . . . ?
C1 C6 C7 C8 -0.4(3) . . . . ?
C5 C6 C7 C8 -179.4(3) . . . . ?
C1 C6 C7 C11 177.7(3) . . . . ?
C5 C6 C7 C11 -1.3(5) . . . . ?
C1 O1 C8 C7 -0.6(3) . . . . ?
C1 O1 C8 C9 -179.7(2) . . . . ?
C11 C7 C8 O1 -177.8(2) . . . . ?
C6 C7 C8 O1 0.6(3) . . . . ?
C11 C7 C8 C9 1.3(4) . . . . ?
C6 C7 C8 C9 179.8(2) . . . . ?
C10 N1 C9 C8 -0.1(4) . . . . ?
C10 N1 C9 C12 178.5(2) . . . . ?
O1 C8 C9 N1 177.4(2) . . . . ?
C7 C8 C9 N1 -1.6(4) . . . . ?
O1 C8 C9 C12 -1.2(4) . . . . ?
C7 C8 C9 C12 179.8(2) . . . . ?
C9 N1 C10 C11 2.2(4) . . . . ?
C9 N1 C10 C17 -176.1(2) . . . . ?
N1 C10 C11 C7 -2.5(4) . . . . ?
C17 C10 C11 C7 175.7(2) . . . . ?
C8 C7 C11 C10 0.7(4) . . . . ?
C6 C7 C11 C10 -177.2(3) . . . . ?
C15 O2 C12 C13 -0.2(3) . . . . ?
C15 O2 C12 C9 -179.7(2) . . . . ?
N1 C9 C12 C13 -174.5(3) . . . . ?
C8 C9 C12 C13 4.1(5) . . . . ?
N1 C9 C12 O2 4.8(3) . . . . ?
C8 C9 C12 O2 -176.6(2) . . . . ?
O2 C12 C13 C14 0.1(3) . . . . ?
C9 C12 C13 C14 179.5(3) . . . . ?
C12 C13 C14 C15 0.1(3) . . . . ?
C13 C14 C15 O2 -0.3(3) . . . . ?
C13 C14 C15 C16 178.9(3) . . . . ?
C12 O2 C15 C14 0.3(3) . . . . ?
C12 O2 C15 C16 -179.0(2) . . . . ?
N1 C10 C17 C18 -0.7(4) . . . . ?
C11 C10 C17 C18 -179.1(3) . . . . ?
N1 C10 C17 C22 177.3(3) . . . . ?
C11 C10 C17 C22 -1.1(4) . . . . ?
C22 C17 C18 C19 0.3(5) . . . . ?
C10 C17 C18 C19 178.4(3) . . . . ?
C17 C18 C19 C20 -0.4(6) . . . . ?
C18 C19 C20 C21 -0.1(6) . . . . ?
C18 C19 C20 C23 -178.5(3) . . . . ?
C19 C20 C21 C22 0.8(6) . . . . ?
C23 C20 C21 C22 179.2(4) . . . . ?
C20 C21 C22 C17 -1.0(7) . . . . ?
C18 C17 C22 C21 0.4(6) . . . . ?
C10 C17 C22 C21 -177.7(3) . . . . ?
C19 C20 C23 F2' -76.9(7) . . . . ?
C21 C20 C23 F2' 104.7(7) . . . . ?
C19 C20 C23 F3' 124.1(7) . . . . ?
C21 C20 C23 F3' -54.3(7) . . . . ?
C19 C20 C23 F1 84.2(6) . . . . ?
C21 C20 C23 F1 -94.2(6) . . . . ?
C19 C20 C23 F2 -35.8(6) . . . . ?
C21 C20 C23 F2 145.8(6) . . . . ?
C19 C20 C23 F3 -158.3(4) . . . . ?
C21 C20 C23 F3 23.3(5) . . . . ?
C19 C20 C23 F1' 27.7(6) . . . . ?
C21 C20 C23 F1' -150.7(5) . . . . ?

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
C16 H16C N1 0.98 2.62 3.419(4) 139.2 1_545
C13 H13 O1 0.95 2.61 3.086(3) 111.3 .
C11 H11 F2' 0.95 2.61 3.492(7) 154.6 2_656
C16 H16C N1 0.98 2.62 3.419(4) 139.2 1_545
C13 H13 O1 0.95 2.61 3.086(3) 111.3 .
C11 H11 F2' 0.95 2.61 3.492(7) 154.6 2_656
C11 H11 F2' 0.95 2.61 3.492(7) 154.6 2_656
C13 H13 O1 0.95 2.61 3.086(3) 111.3 .
C16 H16C N1 0.98 2.62 3.419(4) 139.2 1_545
C11 H11 F2' 0.95 2.61 3.492(7) 154.6 2_656
C13 H13 O1 0.95 2.61 3.086(3) 111.3 .
C16 H16C N1 0.98 2.62 3.419(4) 139.2 1_545
C11 H11 F2' 0.95 2.61 3.492(7) 154.6 2_656
C13 H13 O1 0.95 2.61 3.086(3) 111.3 .
C16 H16C N1 0.98 2.62 3.419(4) 139.2 1_545

_refine_diff_density_max         0.790
_refine_diff_density_min         -0.615
_refine_diff_density_rms         0.056

_shelxl_version_number           2013-4



