# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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_xuxx160521_0m
_database_code_depnum_ccdc_archive 'CCDC 1484915'
_audit_update_record             
;
2016-06-17 deposited with the CCDC.
2017-01-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H23 F3 N2 O3 S'
_chemical_formula_weight         488.51

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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   p-1

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.856(4)
_cell_length_b                   10.755(5)
_cell_length_c                   12.812(6)
_cell_angle_alpha                101.231(17)
_cell_angle_beta                 95.114(15)
_cell_angle_gamma                109.650(15)
_cell_volume                     1236.7(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    132
_cell_measurement_theta_min      2.83
_cell_measurement_theta_max      23.55

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.13
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.312
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             508
_exptl_absorpt_coefficient_mu    0.182
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9628
_exptl_absorpt_correction_T_max  0.9767
_exptl_absorpt_process_details   '(SADABS; Bruker, 2000)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            36387
_diffrn_reflns_av_R_equivalents  0.0832
_diffrn_reflns_av_sigmaI/netI    0.0527
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.32
_diffrn_reflns_theta_max         28.36
_reflns_number_total             6127
_reflns_number_gt                4597
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SMART'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0998P)²+0.3225P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6127
_refine_ls_number_parameters     310
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0846
_refine_ls_R_factor_gt           0.0583
_refine_ls_wR_factor_ref         0.1883
_refine_ls_wR_factor_gt          0.1609
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_restrained_S_all      1.082
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.41065(6) 0.71050(5) 0.99579(4) 0.04499(17) Uani 1 1 d . . .
F3 F 0.80888(19) 1.05061(17) 0.83002(15) 0.0891(6) Uani 1 1 d . . .
F1 F 0.83028(19) 0.9440(2) 0.94992(14) 0.0997(7) Uani 1 1 d . . .
F2 F 0.93029(16) 0.9169(2) 0.80932(18) 0.1077(7) Uani 1 1 d . . .
O1 O 0.4094(2) 0.84152(17) 1.04221(14) 0.0640(5) Uani 1 1 d . . .
O2 O 0.4619(2) 0.63583(17) 1.06066(12) 0.0599(4) Uani 1 1 d . . .
N1 N 0.51954(18) 0.73047(16) 0.90521(13) 0.0402(4) Uani 1 1 d . . .
O3 O 0.0419(2) 0.7160(2) 0.52449(19) 0.0853(7) Uani 1 1 d . . .
N2 N 0.6905(2) 0.6904(2) 0.81360(16) 0.0561(5) Uani 1 1 d . . .
C1 C -0.1846(4) 0.3583(5) 0.7415(4) 0.1140(14) Uani 1 1 d . . .
H2A H -0.2175 0.2728 0.7615 0.171 Uiso 1 1 calc R . .
H3A H -0.1780 0.3426 0.6660 0.171 Uiso 1 1 calc R . .
H1A H -0.2528 0.4031 0.7553 0.171 Uiso 1 1 calc R . .
C2 C -0.0366(3) 0.4464(3) 0.8066(3) 0.0732(8) Uani 1 1 d . . .
C3 C -0.0020(3) 0.5842(3) 0.8471(3) 0.0759(8) Uani 1 1 d . . .
H3 H -0.0715 0.6226 0.8341 0.091 Uiso 1 1 calc R . .
C4 C 0.1330(3) 0.6657(3) 0.9062(2) 0.0615(6) Uani 1 1 d . . .
H4 H 0.1548 0.7583 0.9327 0.074 Uiso 1 1 calc R . .
C5 C 0.2360(2) 0.6081(2) 0.92586(16) 0.0443(4) Uani 1 1 d . . .
C18 C 0.5371(2) 0.82983(17) 0.83716(14) 0.0350(4) Uani 1 1 d . . .
H18 H 0.5658 0.9217 0.8832 0.042 Uiso 1 1 calc R . .
C19 C 0.40048(19) 0.79893(18) 0.75846(14) 0.0351(4) Uani 1 1 d . . .
C20 C 0.3283(2) 0.6703(2) 0.68993(16) 0.0432(4) Uani 1 1 d . . .
H20 H 0.3619 0.6004 0.6955 0.052 Uiso 1 1 calc R . .
C21 C 0.2083(2) 0.6452(2) 0.61440(19) 0.0537(5) Uani 1 1 d . . .
H21 H 0.1609 0.5587 0.5697 0.064 Uiso 1 1 calc R . .
C22 C 0.1582(2) 0.7489(3) 0.6050(2) 0.0556(6) Uani 1 1 d . . .
C25 C 0.0032(3) 0.8255(4) 0.5009(3) 0.1034(13) Uani 1 1 d . . .
H25C H -0.0307 0.8660 0.5617 0.155 Uiso 1 1 calc R . .
H25B H -0.0729 0.7914 0.4390 0.155 Uiso 1 1 calc R . .
H25A H 0.0872 0.8926 0.4861 0.155 Uiso 1 1 calc R . .
C24 C 0.3450(2) 0.8996(2) 0.75097(18) 0.0467(5) Uani 1 1 d . . .
H24 H 0.3894 0.9851 0.7978 0.056 Uiso 1 1 calc R . .
C23 C 0.2241(3) 0.8751(3) 0.6746(2) 0.0586(6) Uani 1 1 d . . .
H23 H 0.1878 0.9437 0.6705 0.070 Uiso 1 1 calc R . .
C9 C 0.6728(2) 0.8127(2) 0.78561(16) 0.0410(4) Uani 1 1 d . . .
C8 C 0.6063(3) 0.6562(2) 0.87995(17) 0.0498(5) Uani 1 1 d . . .
H8 H 0.6032 0.5837 0.9104 0.060 Uiso 1 1 calc R . .
C10 C 0.8114(3) 0.9316(3) 0.8437(2) 0.0686(7) Uani 1 1 d . . .
C11 C 0.6572(2) 0.79745(19) 0.66409(15) 0.0384(4) Uani 1 1 d . . .
C12 C 0.6582(3) 0.6808(2) 0.59740(18) 0.0519(5) Uani 1 1 d . . .
H12 H 0.6736 0.6134 0.6273 0.062 Uiso 1 1 calc R . .
C13 C 0.6365(3) 0.6627(2) 0.4865(2) 0.0614(6) Uani 1 1 d . . .
H13 H 0.6364 0.5826 0.4431 0.074 Uiso 1 1 calc R . .
C14 C 0.6151(2) 0.7602(3) 0.43861(18) 0.0542(5) Uani 1 1 d . . .
C15 C 0.6155(3) 0.8772(3) 0.5056(2) 0.0558(6) Uani 1 1 d . . .
H15 H 0.6014 0.9448 0.4753 0.067 Uiso 1 1 calc R . .
C16 C 0.6362(2) 0.8969(2) 0.61649(18) 0.0482(5) Uani 1 1 d . . .
H16 H 0.6362 0.9771 0.6597 0.058 Uiso 1 1 calc R . .
C17 C 0.5932(4) 0.7395(4) 0.3172(2) 0.0848(9) Uani 1 1 d . . .
H17A H 0.6866 0.7693 0.2944 0.127 Uiso 1 1 calc R . .
H17C H 0.5374 0.7914 0.2964 0.127 Uiso 1 1 calc R . .
H17B H 0.5417 0.6449 0.2838 0.127 Uiso 1 1 calc R . .
C6 C 0.2044(3) 0.4695(2) 0.8867(2) 0.0548(5) Uani 1 1 d . . .
H6 H 0.2739 0.4312 0.9001 0.066 Uiso 1 1 calc R . .
C7 C 0.0687(3) 0.3905(3) 0.8281(3) 0.0696(7) Uani 1 1 d . . .
H7 H 0.0465 0.2978 0.8020 0.084 Uiso 1 1 calc R . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 O1 1.4233(18) . ?
S1 O2 1.4316(16) . ?
S1 N1 1.6458(18) . ?
S1 C5 1.744(2) . ?
F3 C10 1.334(4) . ?
F1 C10 1.331(3) . ?
F2 C10 1.334(3) . ?
N1 C8 1.372(3) . ?
N1 C18 1.482(2) . ?
O3 C22 1.370(3) . ?
O3 C25 1.429(4) . ?
N2 C8 1.260(3) . ?
N2 C9 1.488(3) . ?
C1 C2 1.506(4) . ?
C1 H2A 0.9600 . ?
C1 H3A 0.9600 . ?
C1 H1A 0.9600 . ?
C2 C3 1.383(5) . ?
C2 C7 1.395(4) . ?
C3 C4 1.374(4) . ?
C3 H3 0.9300 . ?
C4 C5 1.385(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.392(3) . ?
C18 C19 1.505(2) . ?
C18 C9 1.592(3) . ?
C18 H18 0.9800 . ?
C19 C24 1.381(3) . ?
C19 C20 1.394(3) . ?
C20 C21 1.373(3) . ?
C20 H20 0.9300 . ?
C21 C22 1.385(3) . ?
C21 H21 0.9300 . ?
C22 C23 1.375(4) . ?
C25 H25C 0.9600 . ?
C25 H25B 0.9600 . ?
C25 H25A 0.9600 . ?
C24 C23 1.389(3) . ?
C24 H24 0.9300 . ?
C23 H23 0.9300 . ?
C9 C11 1.522(3) . ?
C9 C10 1.526(3) . ?
C8 H8 0.9300 . ?
C11 C12 1.377(3) . ?
C11 C16 1.392(3) . ?
C12 C13 1.383(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.377(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.377(4) . ?
C14 C17 1.513(3) . ?
C15 C16 1.381(3) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C17 H17A 0.9600 . ?
C17 H17C 0.9600 . ?
C17 H17B 0.9600 . ?
C6 C7 1.372(4) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?

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
O1 S1 O2 120.94(11) . . ?
O1 S1 N1 106.70(10) . . ?
O2 S1 N1 104.36(10) . . ?
O1 S1 C5 108.53(11) . . ?
O2 S1 C5 108.72(10) . . ?
N1 S1 C5 106.72(10) . . ?
C8 N1 C18 109.58(16) . . ?
C8 N1 S1 125.17(14) . . ?
C18 N1 S1 125.24(13) . . ?
C22 O3 C25 117.0(2) . . ?
C8 N2 C9 107.25(17) . . ?
C2 C1 H2A 109.5 . . ?
C2 C1 H3A 109.5 . . ?
H2A C1 H3A 109.5 . . ?
C2 C1 H1A 109.5 . . ?
H2A C1 H1A 109.5 . . ?
H3A C1 H1A 109.5 . . ?
C3 C2 C7 118.4(3) . . ?
C3 C2 C1 120.9(3) . . ?
C7 C2 C1 120.7(3) . . ?
C4 C3 C2 121.4(2) . . ?
C4 C3 H3 119.3 . . ?
C2 C3 H3 119.3 . . ?
C3 C4 C5 119.1(2) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 H4 120.4 . . ?
C4 C5 C6 120.9(2) . . ?
C4 C5 S1 119.99(18) . . ?
C6 C5 S1 119.08(17) . . ?
N1 C18 C19 112.64(15) . . ?
N1 C18 C9 98.77(14) . . ?
C19 C18 C9 115.86(15) . . ?
N1 C18 H18 109.7 . . ?
C19 C18 H18 109.7 . . ?
C9 C18 H18 109.7 . . ?
C24 C19 C20 118.15(17) . . ?
C24 C19 C18 120.24(17) . . ?
C20 C19 C18 121.60(16) . . ?
C21 C20 C19 121.12(19) . . ?
C21 C20 H20 119.4 . . ?
C19 C20 H20 119.4 . . ?
C20 C21 C22 119.9(2) . . ?
C20 C21 H21 120.1 . . ?
C22 C21 H21 120.1 . . ?
O3 C22 C23 124.2(2) . . ?
O3 C22 C21 115.8(2) . . ?
C23 C22 C21 120.0(2) . . ?
O3 C25 H25C 109.5 . . ?
O3 C25 H25B 109.5 . . ?
H25C C25 H25B 109.5 . . ?
O3 C25 H25A 109.5 . . ?
H25C C25 H25A 109.5 . . ?
H25B C25 H25A 109.5 . . ?
C19 C24 C23 121.0(2) . . ?
C19 C24 H24 119.5 . . ?
C23 C24 H24 119.5 . . ?
C22 C23 C24 119.7(2) . . ?
C22 C23 H23 120.1 . . ?
C24 C23 H23 120.1 . . ?
N2 C9 C11 110.32(16) . . ?
N2 C9 C10 105.34(19) . . ?
C11 C9 C10 110.84(18) . . ?
N2 C9 C18 105.98(15) . . ?
C11 C9 C18 114.80(15) . . ?
C10 C9 C18 109.03(18) . . ?
N2 C8 N1 117.06(18) . . ?
N2 C8 H8 121.5 . . ?
N1 C8 H8 121.5 . . ?
F1 C10 F3 105.7(2) . . ?
F1 C10 F2 107.3(2) . . ?
F3 C10 F2 107.6(2) . . ?
F1 C10 C9 112.0(2) . . ?
F3 C10 C9 112.4(2) . . ?
F2 C10 C9 111.6(2) . . ?
C12 C11 C16 117.99(19) . . ?
C12 C11 C9 120.12(18) . . ?
C16 C11 C9 121.85(17) . . ?
C11 C12 C13 120.7(2) . . ?
C11 C12 H12 119.7 . . ?
C13 C12 H12 119.7 . . ?
C14 C13 C12 121.8(2) . . ?
C14 C13 H13 119.1 . . ?
C12 C13 H13 119.1 . . ?
C15 C14 C13 117.4(2) . . ?
C15 C14 C17 121.5(2) . . ?
C13 C14 C17 121.1(3) . . ?
C14 C15 C16 121.7(2) . . ?
C14 C15 H15 119.2 . . ?
C16 C15 H15 119.2 . . ?
C15 C16 C11 120.5(2) . . ?
C15 C16 H16 119.8 . . ?
C11 C16 H16 119.8 . . ?
C14 C17 H17A 109.5 . . ?
C14 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
C14 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17C C17 H17B 109.5 . . ?
C7 C6 C5 118.8(2) . . ?
C7 C6 H6 120.6 . . ?
C5 C6 H6 120.6 . . ?
C6 C7 C2 121.4(3) . . ?
C6 C7 H7 119.3 . . ?
C2 C7 H7 119.3 . . ?

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
O1 S1 N1 C8 146.73(19) . . . . ?
O2 S1 N1 C8 17.6(2) . . . . ?
C5 S1 N1 C8 -97.38(19) . . . . ?
O1 S1 N1 C18 -34.35(18) . . . . ?
O2 S1 N1 C18 -163.46(15) . . . . ?
C5 S1 N1 C18 81.54(17) . . . . ?
C7 C2 C3 C4 0.7(5) . . . . ?
C1 C2 C3 C4 -179.7(3) . . . . ?
C2 C3 C4 C5 -0.3(4) . . . . ?
C3 C4 C5 C6 -0.1(4) . . . . ?
C3 C4 C5 S1 177.3(2) . . . . ?
O1 S1 C5 C4 11.9(2) . . . . ?
O2 S1 C5 C4 145.18(19) . . . . ?
N1 S1 C5 C4 -102.79(19) . . . . ?
O1 S1 C5 C6 -170.69(17) . . . . ?
O2 S1 C5 C6 -37.4(2) . . . . ?
N1 S1 C5 C6 74.66(19) . . . . ?
C8 N1 C18 C19 112.90(18) . . . . ?
S1 N1 C18 C19 -66.16(19) . . . . ?
C8 N1 C18 C9 -9.95(19) . . . . ?
S1 N1 C18 C9 170.98(13) . . . . ?
N1 C18 C19 C24 129.80(19) . . . . ?
C9 C18 C19 C24 -117.5(2) . . . . ?
N1 C18 C19 C20 -51.6(2) . . . . ?
C9 C18 C19 C20 61.1(2) . . . . ?
C24 C19 C20 C21 2.2(3) . . . . ?
C18 C19 C20 C21 -176.43(19) . . . . ?
C19 C20 C21 C22 0.5(3) . . . . ?
C25 O3 C22 C23 10.7(4) . . . . ?
C25 O3 C22 C21 -169.8(3) . . . . ?
C20 C21 C22 O3 177.3(2) . . . . ?
C20 C21 C22 C23 -3.1(4) . . . . ?
C20 C19 C24 C23 -2.4(3) . . . . ?
C18 C19 C24 C23 176.3(2) . . . . ?
O3 C22 C23 C24 -177.6(2) . . . . ?
C21 C22 C23 C24 2.9(4) . . . . ?
C19 C24 C23 C22 -0.1(4) . . . . ?
C8 N2 C9 C11 -133.9(2) . . . . ?
C8 N2 C9 C10 106.4(2) . . . . ?
C8 N2 C9 C18 -9.0(2) . . . . ?
N1 C18 C9 N2 11.14(18) . . . . ?
C19 C18 C9 N2 -109.36(18) . . . . ?
N1 C18 C9 C11 133.17(16) . . . . ?
C19 C18 C9 C11 12.7(2) . . . . ?
N1 C18 C9 C10 -101.8(2) . . . . ?
C19 C18 C9 C10 137.69(19) . . . . ?
C9 N2 C8 N1 2.7(3) . . . . ?
C18 N1 C8 N2 5.5(3) . . . . ?
S1 N1 C8 N2 -175.48(17) . . . . ?
N2 C9 C10 F1 -58.4(3) . . . . ?
C11 C9 C10 F1 -177.7(2) . . . . ?
C18 C9 C10 F1 54.9(3) . . . . ?
N2 C9 C10 F3 -177.2(2) . . . . ?
C11 C9 C10 F3 63.4(3) . . . . ?
C18 C9 C10 F3 -63.9(3) . . . . ?
N2 C9 C10 F2 61.8(3) . . . . ?
C11 C9 C10 F2 -57.5(3) . . . . ?
C18 C9 C10 F2 175.2(2) . . . . ?
N2 C9 C11 C12 1.1(3) . . . . ?
C10 C9 C11 C12 117.4(2) . . . . ?
C18 C9 C11 C12 -118.5(2) . . . . ?
N2 C9 C11 C16 178.68(18) . . . . ?
C10 C9 C11 C16 -65.0(3) . . . . ?
C18 C9 C11 C16 59.0(2) . . . . ?
C16 C11 C12 C13 -1.0(3) . . . . ?
C9 C11 C12 C13 176.6(2) . . . . ?
C11 C12 C13 C14 0.8(4) . . . . ?
C12 C13 C14 C15 -0.2(4) . . . . ?
C12 C13 C14 C17 179.3(3) . . . . ?
C13 C14 C15 C16 -0.1(4) . . . . ?
C17 C14 C15 C16 -179.6(2) . . . . ?
C14 C15 C16 C11 -0.2(3) . . . . ?
C12 C11 C16 C15 0.7(3) . . . . ?
C9 C11 C16 C15 -176.91(19) . . . . ?
C4 C5 C6 C7 0.0(4) . . . . ?
S1 C5 C6 C7 -177.4(2) . . . . ?
C5 C6 C7 C2 0.4(4) . . . . ?
C3 C2 C7 C6 -0.7(5) . . . . ?
C1 C2 C7 C6 179.6(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.472
_refine_diff_density_min         -0.506
_refine_diff_density_rms         0.148
####################################################################### 
# 
# 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_xuxx160516_0m
_database_code_depnum_ccdc_archive 'CCDC 1481513'
_audit_update_record             
;
2016-05-24 deposited with the CCDC.
2017-01-19 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H13 F3 N2 O'
_chemical_formula_weight         306.28

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c  '

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.299(6)
_cell_length_b                   10.333(5)
_cell_length_c                   13.186(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.62(3)
_cell_angle_gamma                90.00
_cell_volume                     1496.3(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2059
_cell_measurement_theta_min      1.68
_cell_measurement_theta_max      25.05

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.14
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.360
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             632
_exptl_absorpt_coefficient_mu    0.112
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9769
_exptl_absorpt_correction_T_max  0.9845
_exptl_absorpt_process_details   'SADABS(Sheldrick, 1996)'

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX CCD area-detector'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            20328
_diffrn_reflns_av_R_equivalents  0.0893
_diffrn_reflns_av_sigmaI/netI    0.0650
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.53
_diffrn_reflns_theta_max         28.34
_reflns_number_total             3715
_reflns_number_gt                2440
_reflns_threshold_expression     >2sigma(I)

__computing_data_collection      'SMART (Bruker, 1997)'
_computing_cell_refinement       'SMART (Bruker, 1997)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97(Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXTL-PLUS (Sheldrick, 1990)'
_computing_publication_material  SHELXL-97

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0713P)²+0.7998P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.028(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3715
_refine_ls_number_parameters     201
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1063
_refine_ls_R_factor_gt           0.0657
_refine_ls_wR_factor_ref         0.1859
_refine_ls_wR_factor_gt          0.1524
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.051
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
F1 F 0.64322(13) 0.40270(12) 0.28264(13) 0.0616(4) Uani 1 1 d . . .
F2 F 0.57087(14) 0.41480(14) 0.11700(14) 0.0707(5) Uani 1 1 d . . .
F3 F 0.76310(15) 0.39321(16) 0.17902(16) 0.0801(6) Uani 1 1 d . . .
O1 O 0.51489(15) 0.72910(16) 0.10873(13) 0.0516(4) Uani 1 1 d . . .
N1 N 0.46676(17) 0.60367(18) 0.34637(16) 0.0482(5) Uani 1 1 d . . .
N2 N 0.69181(18) 0.6379(2) 0.09481(15) 0.0514(5) Uani 1 1 d . . .
C2 C 0.2763(2) 0.4924(3) 0.3148(3) 0.0746(9) Uani 1 1 d . . .
H2 H 0.2150 0.4552 0.3414 0.090 Uiso 1 1 calc R . .
C1 C 0.3765(2) 0.5479(3) 0.3810(2) 0.0646(7) Uani 1 1 d . . .
H1 H 0.3816 0.5465 0.4524 0.078 Uiso 1 1 calc R . .
C5 C 0.45796(17) 0.60376(18) 0.24397(17) 0.0374(5) Uani 1 1 d . . .
C6 C 0.56032(17) 0.67348(18) 0.21089(16) 0.0367(5) Uani 1 1 d . . .
H6 H 0.5865 0.7449 0.2599 0.044 Uiso 1 1 calc R . .
C8 C 0.67840(18) 0.59889(19) 0.19899(16) 0.0363(5) Uani 1 1 d . . .
C10 C 0.79085(17) 0.63339(19) 0.28355(16) 0.0363(4) Uani 1 1 d . . .
C15 C 0.9007(2) 0.6599(3) 0.2582(2) 0.0532(6) Uani 1 1 d . . .
H15 H 0.9059 0.6566 0.1889 0.064 Uiso 1 1 calc R . .
C14 C 1.0028(2) 0.6912(3) 0.3353(2) 0.0669(8) Uani 1 1 d . . .
H14 H 1.0756 0.7086 0.3167 0.080 Uiso 1 1 calc R . .
C13 C 0.9992(2) 0.6973(3) 0.4386(2) 0.0629(7) Uani 1 1 d . . .
C16 C 1.1106(3) 0.7319(4) 0.5229(3) 0.1071(14) Uani 1 1 d . . .
H16C H 1.1826 0.7061 0.5014 0.161 Uiso 1 1 calc R . .
H16A H 1.1074 0.6880 0.5864 0.161 Uiso 1 1 calc R . .
H16B H 1.1124 0.8237 0.5345 0.161 Uiso 1 1 calc R . .
C3 C 0.2682(2) 0.4929(3) 0.2103(3) 0.0674(8) Uani 1 1 d . . .
H3 H 0.2018 0.4551 0.1647 0.081 Uiso 1 1 calc R . .
C4 C 0.36013(19) 0.5504(2) 0.1724(2) 0.0503(6) Uani 1 1 d . . .
H4 H 0.3563 0.5531 0.1012 0.060 Uiso 1 1 calc R . .
C9 C 0.6636(2) 0.4518(2) 0.1950(2) 0.0490(6) Uani 1 1 d . . .
C12 C 0.8890(2) 0.6700(3) 0.4634(2) 0.0630(7) Uani 1 1 d . . .
H12 H 0.8840 0.6730 0.5327 0.076 Uiso 1 1 calc R . .
C11 C 0.7867(2) 0.6386(3) 0.38722(18) 0.0512(6) Uani 1 1 d . . .
H11 H 0.7141 0.6206 0.4060 0.061 Uiso 1 1 calc R . .
C7 C 0.5993(2) 0.7054(2) 0.05483(19) 0.0538(6) Uani 1 1 d . . .
H7 H 0.5899 0.7386 -0.0121 0.065 Uiso 1 1 calc R . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
F1 C9 1.331(3) . ?
F2 C9 1.339(3) . ?
F3 C9 1.337(3) . ?
O1 C7 1.340(3) . ?
O1 C6 1.443(3) . ?
N1 C5 1.330(3) . ?
N1 C1 1.342(3) . ?
N2 C7 1.264(3) . ?
N2 C8 1.473(3) . ?
C2 C3 1.359(5) . ?
C2 C1 1.381(4) . ?
C2 H2 0.9300 . ?
C1 H1 0.9300 . ?
C5 C4 1.387(3) . ?
C5 C6 1.512(3) . ?
C6 C8 1.580(3) . ?
C6 H6 0.9800 . ?
C8 C10 1.522(3) . ?
C8 C9 1.529(3) . ?
C10 C11 1.380(3) . ?
C10 C15 1.387(3) . ?
C15 C14 1.384(3) . ?
C15 H15 0.9300 . ?
C14 C13 1.374(4) . ?
C14 H14 0.9300 . ?
C13 C12 1.389(4) . ?
C13 C16 1.512(4) . ?
C16 H16C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C3 C4 1.387(4) . ?
C3 H3 0.9300 . ?
C4 H4 0.9300 . ?
C12 C11 1.379(3) . ?
C12 H12 0.9300 . ?
C11 H11 0.9300 . ?
C7 H7 0.9300 . ?

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
C7 O1 C6 106.32(17) . . ?
C5 N1 C1 117.7(2) . . ?
C7 N2 C8 106.5(2) . . ?
C3 C2 C1 119.2(3) . . ?
C3 C2 H2 120.4 . . ?
C1 C2 H2 120.4 . . ?
N1 C1 C2 122.6(3) . . ?
N1 C1 H1 118.7 . . ?
C2 C1 H1 118.7 . . ?
N1 C5 C4 123.2(2) . . ?
N1 C5 C6 114.44(18) . . ?
C4 C5 C6 122.3(2) . . ?
O1 C6 C5 109.33(16) . . ?
O1 C6 C8 102.98(16) . . ?
C5 C6 C8 121.17(16) . . ?
O1 C6 H6 107.6 . . ?
C5 C6 H6 107.6 . . ?
C8 C6 H6 107.6 . . ?
N2 C8 C10 111.56(17) . . ?
N2 C8 C9 105.92(18) . . ?
C10 C8 C9 108.90(17) . . ?
N2 C8 C6 103.52(17) . . ?
C10 C8 C6 113.06(16) . . ?
C9 C8 C6 113.59(16) . . ?
C11 C10 C15 118.1(2) . . ?
C11 C10 C8 121.18(18) . . ?
C15 C10 C8 120.7(2) . . ?
C14 C15 C10 120.5(2) . . ?
C14 C15 H15 119.7 . . ?
C10 C15 H15 119.7 . . ?
C13 C14 C15 121.6(2) . . ?
C13 C14 H14 119.2 . . ?
C15 C14 H14 119.2 . . ?
C14 C13 C12 117.5(2) . . ?
C14 C13 C16 121.7(3) . . ?
C12 C13 C16 120.8(3) . . ?
C13 C16 H16C 109.5 . . ?
C13 C16 H16A 109.5 . . ?
H16C C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
H16C C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C2 C3 C4 119.3(3) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 H3 120.3 . . ?
C5 C4 C3 118.0(3) . . ?
C5 C4 H4 121.0 . . ?
C3 C4 H4 121.0 . . ?
F1 C9 F3 106.8(2) . . ?
F1 C9 F2 107.1(2) . . ?
F3 C9 F2 106.56(19) . . ?
F1 C9 C8 112.87(19) . . ?
F3 C9 C8 111.47(19) . . ?
F2 C9 C8 111.7(2) . . ?
C11 C12 C13 121.4(2) . . ?
C11 C12 H12 119.3 . . ?
C13 C12 H12 119.3 . . ?
C12 C11 C10 120.9(2) . . ?
C12 C11 H11 119.6 . . ?
C10 C11 H11 119.6 . . ?
N2 C7 O1 120.1(2) . . ?
N2 C7 H7 119.9 . . ?
O1 C7 H7 119.9 . . ?

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
C5 N1 C1 C2 -0.5(4) . . . . ?
C3 C2 C1 N1 0.6(4) . . . . ?
C1 N1 C5 C4 0.6(3) . . . . ?
C1 N1 C5 C6 177.5(2) . . . . ?
C7 O1 C6 C5 -136.95(18) . . . . ?
C7 O1 C6 C8 -6.9(2) . . . . ?
N1 C5 C6 O1 -148.93(17) . . . . ?
C4 C5 C6 O1 27.9(3) . . . . ?
N1 C5 C6 C8 91.7(2) . . . . ?
C4 C5 C6 C8 -91.4(2) . . . . ?
C7 N2 C8 C10 -127.1(2) . . . . ?
C7 N2 C8 C9 114.6(2) . . . . ?
C7 N2 C8 C6 -5.2(2) . . . . ?
O1 C6 C8 N2 7.33(19) . . . . ?
C5 C6 C8 N2 129.77(19) . . . . ?
O1 C6 C8 C10 128.20(17) . . . . ?
C5 C6 C8 C10 -109.4(2) . . . . ?
O1 C6 C8 C9 -107.1(2) . . . . ?
C5 C6 C8 C9 15.4(3) . . . . ?
N2 C8 C10 C11 162.3(2) . . . . ?
C9 C8 C10 C11 -81.2(3) . . . . ?
C6 C8 C10 C11 46.1(3) . . . . ?
N2 C8 C10 C15 -18.1(3) . . . . ?
C9 C8 C10 C15 98.5(2) . . . . ?
C6 C8 C10 C15 -134.3(2) . . . . ?
C11 C10 C15 C14 -0.3(4) . . . . ?
C8 C10 C15 C14 -180.0(2) . . . . ?
C10 C15 C14 C13 0.0(5) . . . . ?
C15 C14 C13 C12 0.3(5) . . . . ?
C15 C14 C13 C16 -179.8(3) . . . . ?
C1 C2 C3 C4 -0.8(4) . . . . ?
N1 C5 C4 C3 -0.8(3) . . . . ?
C6 C5 C4 C3 -177.4(2) . . . . ?
C2 C3 C4 C5 0.9(4) . . . . ?
N2 C8 C9 F1 -176.30(17) . . . . ?
C10 C8 C9 F1 63.6(2) . . . . ?
C6 C8 C9 F1 -63.4(2) . . . . ?
N2 C8 C9 F3 63.6(2) . . . . ?
C10 C8 C9 F3 -56.5(3) . . . . ?
C6 C8 C9 F3 176.50(19) . . . . ?
N2 C8 C9 F2 -55.5(2) . . . . ?
C10 C8 C9 F2 -175.63(18) . . . . ?
C6 C8 C9 F2 57.4(3) . . . . ?
C14 C13 C12 C11 -0.3(5) . . . . ?
C16 C13 C12 C11 179.8(3) . . . . ?
C13 C12 C11 C10 -0.1(5) . . . . ?
C15 C10 C11 C12 0.4(4) . . . . ?
C8 C10 C11 C12 -179.9(2) . . . . ?
C8 N2 C7 O1 0.9(3) . . . . ?
C6 O1 C7 N2 4.3(3) . . . . ?

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
C7 H7 N1 0.93 2.62 3.428(4) 146.1 4_575

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.306
_refine_diff_density_min         -0.253
_refine_diff_density_rms         0.050
