# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_1
_database_code_depnum_ccdc_archive 'CCDC 1471857'
_audit_update_record             
;
2016-04-01 deposited with the CCDC.
2016-10-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C18 H14 F3 N O2'
_chemical_formula_weight         333.30

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   P21/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                   15.907(2)
_cell_length_b                   11.3687(16)
_cell_length_c                   17.799(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.223(2)
_cell_angle_gamma                90.00
_cell_volume                     3177.3(8)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    864
_cell_measurement_theta_min      2.52
_cell_measurement_theta_max      25.84

_exptl_crystal_description       BLOCKS
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.09
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.394
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1376
_exptl_absorpt_coefficient_mu    0.115
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.9632
_exptl_absorpt_correction_T_max  0.9898
_exptl_absorpt_process_details   'BRUKER SADABS'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(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 SMART APEX CCD DIFFRACTOMETER'
_diffrn_measurement_method       'OMEGA-PHI SCAN'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            15465
_diffrn_reflns_av_R_equivalents  0.0494
_diffrn_reflns_av_sigmaI/netI    0.0561
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.30
_diffrn_reflns_theta_max         25.00
_reflns_number_total             5590
_reflns_number_gt                4276
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'BRUKER SMART'
_computing_cell_refinement       'BRUKER SMART'
_computing_data_reduction        'BRUKER SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ORTEP
_computing_publication_material  ?

_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)+(0.1080P)²+0.1612P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    CONSTR
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5590
_refine_ls_number_parameters     437
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0754
_refine_ls_R_factor_gt           0.0571
_refine_ls_wR_factor_ref         0.1695
_refine_ls_wR_factor_gt          0.1530
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_restrained_S_all      1.043
_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
N1 N 0.92857(12) 0.41816(15) 0.48864(10) 0.0263(4) Uani 1 1 d . . .
N2 N 0.13058(12) 0.32955(17) 0.37621(11) 0.0308(5) Uani 1 1 d . . .
F1 F 0.62558(10) 0.15300(16) 0.41903(9) 0.0584(5) Uani 1 1 d . . .
F2 F 0.72416(11) 0.20606(17) 0.35760(9) 0.0634(5) Uani 1 1 d . . .
F3 F 0.62952(10) 0.33029(17) 0.37915(10) 0.0619(5) Uani 1 1 d . . .
F4 F 0.29308(10) -0.01457(12) 0.23846(9) 0.0480(4) Uani 1 1 d . . .
F5 F 0.24885(10) 0.02706(14) 0.34334(9) 0.0518(4) Uani 1 1 d . . .
F6 F 0.36833(9) 0.09538(14) 0.32148(8) 0.0469(4) Uani 1 1 d . . .
O1 O 0.78383(10) 0.37379(13) 0.46820(9) 0.0328(4) Uani 1 1 d . . .
O2 O 0.89814(10) 0.53254(13) 0.46531(9) 0.0294(4) Uani 1 1 d . . .
H2 H 0.9383 0.5785 0.4692 0.044 Uiso 1 1 calc R . .
O3 O 0.23808(10) 0.25902(14) 0.31362(8) 0.0311(4) Uani 1 1 d . . .
O4 O 0.20058(10) 0.37758(16) 0.42545(9) 0.0370(4) Uani 1 1 d . . .
H4 H 0.1839 0.4074 0.4624 0.056 Uiso 1 1 calc R . .
C1 C 0.64817(16) 0.2273(3) 0.58925(15) 0.0453(7) Uani 1 1 d . . .
H1 H 0.6658 0.1495 0.5873 0.054 Uiso 1 1 calc R . .
C2 C 0.59449(17) 0.2592(3) 0.64000(16) 0.0561(8) Uani 1 1 d . . .
H2A H 0.5769 0.2023 0.6717 0.067 Uiso 1 1 calc R . .
C3 C 0.56684(18) 0.3726(3) 0.64449(18) 0.0623(10) Uani 1 1 d . . .
C4 C 0.5946(2) 0.4541(3) 0.5963(2) 0.0738(11) Uani 1 1 d . . .
H4A H 0.5766 0.5317 0.5981 0.089 Uiso 1 1 calc R . .
C5 C 0.64803(19) 0.4237(3) 0.5458(2) 0.0584(8) Uani 1 1 d . . .
H5 H 0.6656 0.4807 0.5142 0.070 Uiso 1 1 calc R . .
C6 C 0.67561(15) 0.3095(2) 0.54166(14) 0.0358(6) Uani 1 1 d . . .
C7 C 0.73285(15) 0.2739(2) 0.48466(14) 0.0332(6) Uani 1 1 d . . .
C8 C 0.86740(14) 0.3461(2) 0.48856(12) 0.0267(5) Uani 1 1 d . . .
C9 C 0.87668(15) 0.22260(19) 0.51349(13) 0.0290(5) Uani 1 1 d . . .
C10 C 0.79811(15) 0.1814(2) 0.51153(14) 0.0334(6) Uani 1 1 d . . .
H10 H 0.7853 0.1052 0.5250 0.040 Uiso 1 1 calc R . .
C11 C 0.95973(15) 0.16742(19) 0.54008(13) 0.0286(5) Uani 1 1 d . . .
C12 C 1.02923(15) 0.1883(2) 0.50303(14) 0.0319(5) Uani 1 1 d . . .
H12 H 1.0225 0.2359 0.4600 0.038 Uiso 1 1 calc R . .
C13 C 1.10795(16) 0.1393(2) 0.52955(14) 0.0366(6) Uani 1 1 d . . .
H13 H 1.1539 0.1544 0.5046 0.044 Uiso 1 1 calc R . .
C14 C 1.11826(17) 0.0679(2) 0.59301(15) 0.0402(6) Uani 1 1 d . . .
H14 H 1.1713 0.0356 0.6114 0.048 Uiso 1 1 calc R . .
C15 C 1.04979(18) 0.0445(2) 0.62903(15) 0.0424(6) Uani 1 1 d . . .
H15 H 1.0566 -0.0051 0.6711 0.051 Uiso 1 1 calc R . .
C16 C 0.97105(16) 0.0938(2) 0.60353(14) 0.0364(6) Uani 1 1 d . . .
H16 H 0.9254 0.0778 0.6287 0.044 Uiso 1 1 calc R . .
C17 C 0.67809(17) 0.2407(3) 0.40918(15) 0.0433(7) Uani 1 1 d . . .
C18 C 0.5082(2) 0.4070(4) 0.6994(2) 0.0985(16) Uani 1 1 d . . .
H18A H 0.4505 0.3887 0.6777 0.148 Uiso 1 1 calc R . .
H18B H 0.5132 0.4900 0.7094 0.148 Uiso 1 1 calc R . .
H18C H 0.5235 0.3644 0.7462 0.148 Uiso 1 1 calc R . .
C19 C 0.28692(15) 0.1825(2) 0.12210(14) 0.0350(6) Uani 1 1 d . . .
H19 H 0.2554 0.1142 0.1105 0.042 Uiso 1 1 calc R . .
C20 C 0.32966(15) 0.2318(2) 0.06829(14) 0.0365(6) Uani 1 1 d . . .
H20 H 0.3264 0.1959 0.0210 0.044 Uiso 1 1 calc R . .
C21 C 0.37701(16) 0.3330(2) 0.08314(14) 0.0378(6) Uani 1 1 d . . .
C22 C 0.37975(19) 0.3842(2) 0.15367(16) 0.0491(7) Uani 1 1 d . . .
H22 H 0.4107 0.4531 0.1647 0.059 Uiso 1 1 calc R . .
C23 C 0.33746(17) 0.3354(2) 0.20869(15) 0.0416(6) Uani 1 1 d . . .
H23 H 0.3408 0.3713 0.2560 0.050 Uiso 1 1 calc R . .
C24 C 0.29034(14) 0.2333(2) 0.19303(12) 0.0279(5) Uani 1 1 d . . .
C25 C 0.24178(14) 0.17935(19) 0.25145(13) 0.0292(5) Uani 1 1 d . . .
C26 C 0.15471(14) 0.27186(19) 0.32219(12) 0.0266(5) Uani 1 1 d . . .
C27 C 0.09941(14) 0.20832(18) 0.26164(12) 0.0256(5) Uani 1 1 d . . .
C28 C 0.15101(14) 0.15291(19) 0.22111(13) 0.0294(5) Uani 1 1 d . . .
H28 H 0.1328 0.1044 0.1796 0.035 Uiso 1 1 calc R . .
C29 C 0.00562(14) 0.20679(19) 0.24958(12) 0.0265(5) Uani 1 1 d . . .
C30 C -0.04088(15) 0.2835(2) 0.28790(13) 0.0333(6) Uani 1 1 d . . .
H30 H -0.0125 0.3377 0.3221 0.040 Uiso 1 1 calc R . .
C31 C -0.12893(15) 0.2800(2) 0.27562(14) 0.0391(6) Uani 1 1 d . . .
H31 H -0.1593 0.3320 0.3014 0.047 Uiso 1 1 calc R . .
C32 C -0.17207(16) 0.1999(2) 0.22531(14) 0.0403(6) Uani 1 1 d . . .
H32 H -0.2313 0.1974 0.2176 0.048 Uiso 1 1 calc R . .
C33 C -0.12702(15) 0.1238(2) 0.18650(13) 0.0362(6) Uani 1 1 d . . .
H33 H -0.1559 0.0702 0.1522 0.043 Uiso 1 1 calc R . .
C34 C -0.03918(14) 0.1271(2) 0.19842(13) 0.0315(5) Uani 1 1 d . . .
H34 H -0.0093 0.0753 0.1720 0.038 Uiso 1 1 calc R . .
C35 C 0.28903(15) 0.0713(2) 0.28917(14) 0.0366(6) Uani 1 1 d . . .
C36 C 0.4225(2) 0.3859(3) 0.02343(17) 0.0538(8) Uani 1 1 d . . .
H36A H 0.4530 0.3255 0.0015 0.081 Uiso 1 1 calc R . .
H36B H 0.4619 0.4447 0.0463 0.081 Uiso 1 1 calc R . .
H36C H 0.3817 0.4214 -0.0156 0.081 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
N1 C8 1.272(3) . ?
N1 O2 1.426(2) . ?
N2 C26 1.273(3) . ?
N2 O4 1.412(2) . ?
F1 C17 1.331(3) . ?
F2 C17 1.323(3) . ?
F3 C17 1.337(3) . ?
F4 C35 1.338(3) . ?
F5 C35 1.338(3) . ?
F6 C35 1.328(3) . ?
O1 C8 1.358(3) . ?
O1 C7 1.453(3) . ?
O2 H2 0.8200 . ?
O3 C26 1.367(3) . ?
O3 C25 1.439(3) . ?
O4 H4 0.8200 . ?
C1 C6 1.379(4) . ?
C1 C2 1.387(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.368(5) . ?
C2 H2A 0.9300 . ?
C3 C4 1.382(5) . ?
C3 C18 1.508(4) . ?
C4 C5 1.378(4) . ?
C4 H4A 0.9300 . ?
C5 C6 1.376(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.523(3) . ?
C7 C10 1.501(3) . ?
C7 C17 1.527(4) . ?
C8 C9 1.472(3) . ?
C9 C10 1.330(3) . ?
C9 C11 1.470(3) . ?
C10 H10 0.9300 . ?
C11 C16 1.394(3) . ?
C11 C12 1.395(3) . ?
C12 C13 1.383(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.380(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.375(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.381(4) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 C20 1.379(3) . ?
C19 C24 1.381(3) . ?
C19 H19 0.9300 . ?
C20 C21 1.377(4) . ?
C20 H20 0.9300 . ?
C21 C22 1.378(4) . ?
C21 C36 1.504(3) . ?
C22 C23 1.389(3) . ?
C22 H22 0.9300 . ?
C23 C24 1.386(3) . ?
C23 H23 0.9300 . ?
C24 C25 1.520(3) . ?
C25 C28 1.489(3) . ?
C25 C35 1.537(3) . ?
C26 C27 1.467(3) . ?
C27 C28 1.334(3) . ?
C27 C29 1.473(3) . ?
C28 H28 0.9300 . ?
C29 C30 1.391(3) . ?
C29 C34 1.397(3) . ?
C30 C31 1.383(3) . ?
C30 H30 0.9300 . ?
C31 C32 1.380(4) . ?
C31 H31 0.9300 . ?
C32 C33 1.378(3) . ?
C32 H32 0.9300 . ?
C33 C34 1.380(3) . ?
C33 H33 0.9300 . ?
C34 H34 0.9300 . ?
C36 H36A 0.9600 . ?
C36 H36B 0.9600 . ?
C36 H36C 0.9600 . ?

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 N1 O2 111.31(17) . . ?
C26 N2 O4 111.40(18) . . ?
C8 O1 C7 108.60(17) . . ?
N1 O2 H2 109.5 . . ?
C26 O3 C25 108.24(17) . . ?
N2 O4 H4 109.5 . . ?
C6 C1 C2 120.7(3) . . ?
C6 C1 H1 119.6 . . ?
C2 C1 H1 119.6 . . ?
C3 C2 C1 121.4(3) . . ?
C3 C2 H2A 119.3 . . ?
C1 C2 H2A 119.3 . . ?
C2 C3 C4 117.3(3) . . ?
C2 C3 C18 121.4(4) . . ?
C4 C3 C18 121.3(4) . . ?
C5 C4 C3 121.9(3) . . ?
C5 C4 H4A 119.0 . . ?
C3 C4 H4A 119.0 . . ?
C6 C5 C4 120.5(3) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C5 C6 C1 118.2(2) . . ?
C5 C6 C7 121.1(2) . . ?
C1 C6 C7 120.7(2) . . ?
O1 C7 C10 103.42(17) . . ?
O1 C7 C6 109.82(19) . . ?
C10 C7 C6 115.5(2) . . ?
O1 C7 C17 105.88(19) . . ?
C10 C7 C17 112.0(2) . . ?
C6 C7 C17 109.53(19) . . ?
N1 C8 O1 124.5(2) . . ?
N1 C8 C9 125.0(2) . . ?
O1 C8 C9 110.39(19) . . ?
C10 C9 C11 130.6(2) . . ?
C10 C9 C8 106.2(2) . . ?
C11 C9 C8 123.0(2) . . ?
C9 C10 C7 111.1(2) . . ?
C9 C10 H10 124.4 . . ?
C7 C10 H10 124.4 . . ?
C16 C11 C12 118.4(2) . . ?
C16 C11 C9 120.6(2) . . ?
C12 C11 C9 120.9(2) . . ?
C13 C12 C11 120.8(2) . . ?
C13 C12 H12 119.6 . . ?
C11 C12 H12 119.6 . . ?
C14 C13 C12 119.9(2) . . ?
C14 C13 H13 120.0 . . ?
C12 C13 H13 120.0 . . ?
C15 C14 C13 119.7(2) . . ?
C15 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
C14 C15 C16 120.9(2) . . ?
C14 C15 H15 119.6 . . ?
C16 C15 H15 119.6 . . ?
C15 C16 C11 120.2(2) . . ?
C15 C16 H16 119.9 . . ?
C11 C16 H16 119.9 . . ?
F2 C17 F1 107.3(2) . . ?
F2 C17 F3 107.4(2) . . ?
F1 C17 F3 106.8(2) . . ?
F2 C17 C7 112.5(2) . . ?
F1 C17 C7 110.5(2) . . ?
F3 C17 C7 112.1(2) . . ?
C3 C18 H18A 109.5 . . ?
C3 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C3 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C20 C19 C24 120.9(2) . . ?
C20 C19 H19 119.6 . . ?
C24 C19 H19 119.6 . . ?
C21 C20 C19 121.4(2) . . ?
C21 C20 H20 119.3 . . ?
C19 C20 H20 119.3 . . ?
C20 C21 C22 117.6(2) . . ?
C20 C21 C36 120.6(2) . . ?
C22 C21 C36 121.7(2) . . ?
C21 C22 C23 121.7(2) . . ?
C21 C22 H22 119.1 . . ?
C23 C22 H22 119.1 . . ?
C24 C23 C22 120.0(2) . . ?
C24 C23 H23 120.0 . . ?
C22 C23 H23 120.0 . . ?
C19 C24 C23 118.3(2) . . ?
C19 C24 C25 120.4(2) . . ?
C23 C24 C25 121.2(2) . . ?
O3 C25 C28 104.43(17) . . ?
O3 C25 C24 111.10(18) . . ?
C28 C25 C24 113.77(19) . . ?
O3 C25 C35 104.15(18) . . ?
C28 C25 C35 112.02(19) . . ?
C24 C25 C35 110.77(18) . . ?
N2 C26 O3 123.7(2) . . ?
N2 C26 C27 126.2(2) . . ?
O3 C26 C27 110.11(18) . . ?
C28 C27 C26 106.33(19) . . ?
C28 C27 C29 127.7(2) . . ?
C26 C27 C29 125.94(19) . . ?
C27 C28 C25 110.7(2) . . ?
C27 C28 H28 124.7 . . ?
C25 C28 H28 124.7 . . ?
C30 C29 C34 118.1(2) . . ?
C30 C29 C27 121.8(2) . . ?
C34 C29 C27 120.12(19) . . ?
C31 C30 C29 120.6(2) . . ?
C31 C30 H30 119.7 . . ?
C29 C30 H30 119.7 . . ?
C32 C31 C30 120.5(2) . . ?
C32 C31 H31 119.8 . . ?
C30 C31 H31 119.8 . . ?
C33 C32 C31 119.7(2) . . ?
C33 C32 H32 120.2 . . ?
C31 C32 H32 120.2 . . ?
C32 C33 C34 120.1(2) . . ?
C32 C33 H33 120.0 . . ?
C34 C33 H33 120.0 . . ?
C33 C34 C29 121.1(2) . . ?
C33 C34 H34 119.5 . . ?
C29 C34 H34 119.5 . . ?
F6 C35 F5 107.2(2) . . ?
F6 C35 F4 107.29(19) . . ?
F5 C35 F4 106.97(19) . . ?
F6 C35 C25 112.9(2) . . ?
F5 C35 C25 111.03(19) . . ?
F4 C35 C25 111.2(2) . . ?
C21 C36 H36A 109.5 . . ?
C21 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
C21 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.404
_refine_diff_density_min         -0.339
_refine_diff_density_rms         0.083
####################################################################### 
# 
# 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_rcf3no2m
_database_code_depnum_ccdc_archive 'CCDC 1473287'
_audit_update_record             
;
2016-04-11 deposited with the CCDC.
2016-10-27 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H11 F4 N O2'
_chemical_formula_weight         337.27

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   P21/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                   16.2924(16)
_cell_length_b                   11.4971(11)
_cell_length_c                   17.3169(17)
_cell_angle_alpha                90.00
_cell_angle_beta                 113.234(2)
_cell_angle_gamma                90.00
_cell_volume                     2980.7(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    4518
_cell_measurement_theta_min      2.23
_cell_measurement_theta_max      27.52

_exptl_crystal_description       BLOCKS
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.503
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1376
_exptl_absorpt_coefficient_mu    0.132
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.9490
_exptl_absorpt_correction_T_max  0.9947
_exptl_absorpt_process_details   'BRUKER SADABS'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(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 SMART APEX CCD DIFFARCTOMETER'
_diffrn_measurement_method       'OMEGA-PHI SCAN'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            14500
_diffrn_reflns_av_R_equivalents  0.0326
_diffrn_reflns_av_sigmaI/netI    0.0415
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.36
_diffrn_reflns_theta_max         25.00
_reflns_number_total             5239
_reflns_number_gt                4430
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'BRUKER SMART'
_computing_cell_refinement       'BRUKER SMART'
_computing_data_reduction        'BRUKER SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ORTEP
_computing_publication_material  ?

_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)+(0.0486P)²+2.6975P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5239
_refine_ls_number_parameters     435
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0888
_refine_ls_R_factor_gt           0.0727
_refine_ls_wR_factor_ref         0.1481
_refine_ls_wR_factor_gt          0.1408
_refine_ls_goodness_of_fit_ref   1.227
_refine_ls_restrained_S_all      1.227
_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 0.18632(14) -0.01284(17) 0.69214(14) 0.0485(6) Uani 1 1 d . . .
F2 F 0.10667(13) 0.08524(19) 0.58238(13) 0.0507(6) Uani 1 1 d . . .
F3 F 0.23591(14) 0.02245(19) 0.59626(14) 0.0504(6) Uani 1 1 d . . .
F4 F 0.04372(14) 0.4036(2) 0.85131(14) 0.0520(6) Uani 1 1 d . . .
F5 F 0.11883(13) 0.6840(2) 0.28356(12) 0.0470(6) Uani 1 1 d . . .
F6 F 0.22186(14) 0.7996(2) 0.28267(12) 0.0515(6) Uani 1 1 d . . .
F7 F 0.11843(14) 0.86325(19) 0.31866(13) 0.0488(6) Uani 1 1 d . . .
F8 F 0.01626(15) 0.6439(2) 0.59894(15) 0.0597(7) Uani 1 1 d . . .
O1 O 0.23870(14) 0.25498(19) 0.61952(13) 0.0285(5) Uani 1 1 d . . .
O2 O 0.28226(14) 0.3757(2) 0.51661(13) 0.0305(5) Uani 1 1 d . . .
H2C H 0.3018 0.4104 0.4861 0.046 Uiso 1 1 calc R . .
O3 O 0.27738(13) 0.63914(17) 0.41329(13) 0.0246(5) Uani 1 1 d . . .
O4 O 0.39258(13) 0.47520(17) 0.43938(13) 0.0231(5) Uani 1 1 d . . .
H4C H 0.4333 0.4275 0.4543 0.035 Uiso 1 1 calc R . .
N1 N 0.35393(17) 0.3318(2) 0.58726(15) 0.0257(6) Uani 1 1 d . . .
N2 N 0.42761(16) 0.5878(2) 0.46999(15) 0.0210(6) Uani 1 1 d . . .
C1 C 0.1844(2) 0.1972(3) 0.8048(2) 0.0387(9) Uani 1 1 d . . .
H1 H 0.2198 0.1330 0.8295 0.046 Uiso 1 1 calc R . .
C2 C 0.1381(2) 0.2528(4) 0.8460(2) 0.0406(9) Uani 1 1 d . . .
H2 H 0.1419 0.2263 0.8980 0.049 Uiso 1 1 calc R . .
C3 C 0.0867(2) 0.3468(3) 0.8092(2) 0.0368(8) Uani 1 1 d . . .
C4 C 0.0775(3) 0.3866(3) 0.7321(2) 0.0433(9) Uani 1 1 d . . .
H4 H 0.0410 0.4499 0.7076 0.052 Uiso 1 1 calc R . .
C5 C 0.1236(2) 0.3303(3) 0.6913(2) 0.0381(9) Uani 1 1 d . . .
H5 H 0.1177 0.3561 0.6384 0.046 Uiso 1 1 calc R . .
C6 C 0.1785(2) 0.2364(3) 0.72710(19) 0.0270(7) Uani 1 1 d . . .
C7 C 0.2332(2) 0.1796(3) 0.6839(2) 0.0282(7) Uani 1 1 d . . .
C8 C 0.32695(19) 0.2729(3) 0.63471(18) 0.0224(7) Uani 1 1 d . . .
C9 C 0.3839(2) 0.2122(3) 0.71200(18) 0.0227(7) Uani 1 1 d . . .
C10 C 0.3293(2) 0.1587(3) 0.74079(19) 0.0258(7) Uani 1 1 d . . .
H10 H 0.3480 0.1142 0.7896 0.031 Uiso 1 1 calc R . .
C11 C 0.4826(2) 0.2127(3) 0.74888(18) 0.0233(7) Uani 1 1 d . . .
C12 C 0.5322(2) 0.2934(3) 0.7254(2) 0.0290(7) Uani 1 1 d . . .
H12 H 0.5030 0.3484 0.6843 0.035 Uiso 1 1 calc R . .
C13 C 0.6245(2) 0.2925(3) 0.7623(2) 0.0341(8) Uani 1 1 d . . .
H13 H 0.6567 0.3470 0.7460 0.041 Uiso 1 1 calc R . .
C14 C 0.6692(2) 0.2116(3) 0.8233(2) 0.0321(8) Uani 1 1 d . . .
H14 H 0.7313 0.2116 0.8482 0.038 Uiso 1 1 calc R . .
C15 C 0.6211(2) 0.1308(3) 0.8468(2) 0.0297(8) Uani 1 1 d . . .
H15 H 0.6510 0.0758 0.8876 0.036 Uiso 1 1 calc R . .
C16 C 0.5287(2) 0.1307(3) 0.81033(19) 0.0266(7) Uani 1 1 d . . .
H16 H 0.4971 0.0757 0.8268 0.032 Uiso 1 1 calc R . .
C17 C 0.1895(2) 0.0680(3) 0.6380(2) 0.0378(9) Uani 1 1 d . . .
C18 C 0.1520(2) 0.6012(3) 0.4796(2) 0.0303(8) Uani 1 1 d . . .
H20 H 0.1763 0.5405 0.4600 0.036 Uiso 1 1 calc R . .
C19 C 0.1015(2) 0.5771(3) 0.5258(2) 0.0400(9) Uani 1 1 d . . .
H19 H 0.0928 0.5008 0.5386 0.048 Uiso 1 1 calc R . .
C20 C 0.0647(2) 0.6675(3) 0.5523(2) 0.0379(9) Uani 1 1 d . . .
C21 C 0.0750(2) 0.7806(3) 0.5344(2) 0.0341(8) Uani 1 1 d . . .
H21 H 0.0484 0.8404 0.5524 0.041 Uiso 1 1 calc R . .
C22 C 0.1263(2) 0.8042(3) 0.48871(19) 0.0268(7) Uani 1 1 d . . .
H22 H 0.1340 0.8807 0.4755 0.032 Uiso 1 1 calc R . .
C23 C 0.16629(18) 0.7141(3) 0.46242(18) 0.0222(7) Uani 1 1 d . . .
C24 C 0.22696(19) 0.7415(3) 0.41628(19) 0.0240(7) Uani 1 1 d . . .
C25 C 0.2971(2) 0.8307(3) 0.45878(19) 0.0232(7) Uani 1 1 d . . .
H25 H 0.2855 0.9075 0.4681 0.028 Uiso 1 1 calc R . .
C26 C 0.37863(19) 0.7850(2) 0.48147(17) 0.0199(6) Uani 1 1 d . . .
C27 C 0.36613(19) 0.6634(3) 0.45445(17) 0.0201(6) Uani 1 1 d . . .
C28 C 0.4669(2) 0.8378(2) 0.53012(18) 0.0212(7) Uani 1 1 d . . .
C29 C 0.4771(2) 0.9179(3) 0.59363(19) 0.0255(7) Uani 1 1 d . . .
H29 H 0.4277 0.9401 0.6045 0.031 Uiso 1 1 calc R . .
C30 C 0.5600(2) 0.9645(3) 0.6406(2) 0.0320(8) Uani 1 1 d . . .
H30 H 0.5660 1.0185 0.6825 0.038 Uiso 1 1 calc R . .
C31 C 0.6341(2) 0.9315(3) 0.6257(2) 0.0296(8) Uani 1 1 d . . .
H31 H 0.6902 0.9609 0.6588 0.036 Uiso 1 1 calc R . .
C32 C 0.6244(2) 0.8548(3) 0.5617(2) 0.0276(7) Uani 1 1 d . . .
H32 H 0.6739 0.8342 0.5505 0.033 Uiso 1 1 calc R . .
C33 C 0.5417(2) 0.8082(3) 0.5139(2) 0.0254(7) Uani 1 1 d . . .
H33 H 0.5358 0.7567 0.4706 0.030 Uiso 1 1 calc R . .
C34 C 0.1708(2) 0.7722(3) 0.3239(2) 0.0341(8) 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 C17 1.335(4) . ?
F2 C17 1.328(4) . ?
F3 C17 1.342(4) . ?
F4 C3 1.360(4) . ?
F5 C34 1.329(4) . ?
F6 C34 1.331(4) . ?
F7 C34 1.330(4) . ?
F8 C20 1.360(4) . ?
O1 C8 1.371(3) . ?
O1 C7 1.443(4) . ?
O2 N1 1.410(3) . ?
O2 H2C 0.8200 . ?
O3 C27 1.365(3) . ?
O3 C24 1.448(3) . ?
O4 N2 1.429(3) . ?
O4 H4C 0.8200 . ?
N1 C8 1.270(4) . ?
N2 C27 1.273(4) . ?
C1 C2 1.382(5) . ?
C1 C6 1.386(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.362(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.363(5) . ?
C4 C5 1.380(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.382(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.519(4) . ?
C7 C10 1.503(4) . ?
C7 C17 1.529(5) . ?
C8 C9 1.470(4) . ?
C9 C10 1.330(4) . ?
C9 C11 1.478(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.393(4) . ?
C11 C16 1.398(4) . ?
C12 C13 1.382(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.380(5) . ?
C13 H13 0.9300 . ?
C14 C15 1.375(5) . ?
C14 H14 0.9300 . ?
C15 C16 1.384(4) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C18 C23 1.373(4) . ?
C18 C19 1.383(5) . ?
C18 H20 0.9300 . ?
C19 C20 1.367(5) . ?
C19 H19 0.9300 . ?
C20 C21 1.363(5) . ?
C21 C22 1.386(4) . ?
C21 H21 0.9300 . ?
C22 C23 1.392(4) . ?
C22 H22 0.9300 . ?
C23 C24 1.529(4) . ?
C24 C25 1.495(4) . ?
C24 C34 1.538(5) . ?
C25 C26 1.335(4) . ?
C25 H25 0.9300 . ?
C26 C27 1.463(4) . ?
C26 C28 1.479(4) . ?
C28 C29 1.393(4) . ?
C28 C33 1.397(4) . ?
C29 C30 1.381(5) . ?
C29 H29 0.9300 . ?
C30 C31 1.384(5) . ?
C30 H30 0.9300 . ?
C31 C32 1.376(5) . ?
C31 H31 0.9300 . ?
C32 C33 1.382(4) . ?
C32 H32 0.9300 . ?
C33 H33 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
C8 O1 C7 108.8(2) . . ?
N1 O2 H2C 109.5 . . ?
C27 O3 C24 108.3(2) . . ?
N2 O4 H4C 109.5 . . ?
C8 N1 O2 111.9(2) . . ?
C27 N2 O4 112.0(2) . . ?
C2 C1 C6 120.5(3) . . ?
C2 C1 H1 119.8 . . ?
C6 C1 H1 119.8 . . ?
C3 C2 C1 119.1(3) . . ?
C3 C2 H2 120.5 . . ?
C1 C2 H2 120.5 . . ?
F4 C3 C2 118.8(3) . . ?
F4 C3 C4 118.9(3) . . ?
C2 C3 C4 122.3(3) . . ?
C3 C4 C5 118.2(3) . . ?
C3 C4 H4 120.9 . . ?
C5 C4 H4 120.9 . . ?
C4 C5 C6 121.5(3) . . ?
C4 C5 H5 119.2 . . ?
C6 C5 H5 119.2 . . ?
C5 C6 C1 118.4(3) . . ?
C5 C6 C7 121.1(3) . . ?
C1 C6 C7 120.5(3) . . ?
O1 C7 C10 103.7(2) . . ?
O1 C7 C6 110.4(3) . . ?
C10 C7 C6 114.1(3) . . ?
O1 C7 C17 105.1(3) . . ?
C10 C7 C17 110.9(3) . . ?
C6 C7 C17 111.9(3) . . ?
N1 C8 O1 124.1(3) . . ?
N1 C8 C9 126.0(3) . . ?
O1 C8 C9 109.9(2) . . ?
C10 C9 C8 106.6(3) . . ?
C10 C9 C11 127.9(3) . . ?
C8 C9 C11 125.5(3) . . ?
C9 C10 C7 111.0(3) . . ?
C9 C10 H10 124.5 . . ?
C7 C10 H10 124.5 . . ?
C12 C11 C16 118.2(3) . . ?
C12 C11 C9 122.3(3) . . ?
C16 C11 C9 119.5(3) . . ?
C13 C12 C11 120.7(3) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C14 C13 C12 120.6(3) . . ?
C14 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
C15 C14 C13 119.4(3) . . ?
C15 C14 H14 120.3 . . ?
C13 C14 H14 120.3 . . ?
C14 C15 C16 120.6(3) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 H15 119.7 . . ?
C15 C16 C11 120.5(3) . . ?
C15 C16 H16 119.7 . . ?
C11 C16 H16 119.7 . . ?
F2 C17 F1 107.6(3) . . ?
F2 C17 F3 107.1(3) . . ?
F1 C17 F3 107.0(3) . . ?
F2 C17 C7 112.5(3) . . ?
F1 C17 C7 111.0(3) . . ?
F3 C17 C7 111.2(3) . . ?
C23 C18 C19 120.4(3) . . ?
C23 C18 H20 119.8 . . ?
C19 C18 H20 119.8 . . ?
C20 C19 C18 118.9(3) . . ?
C20 C19 H19 120.6 . . ?
C18 C19 H19 120.6 . . ?
F8 C20 C21 118.5(3) . . ?
F8 C20 C19 118.9(3) . . ?
C21 C20 C19 122.6(3) . . ?
C20 C21 C22 118.3(3) . . ?
C20 C21 H21 120.9 . . ?
C22 C21 H21 120.9 . . ?
C21 C22 C23 120.4(3) . . ?
C21 C22 H22 119.8 . . ?
C23 C22 H22 119.8 . . ?
C18 C23 C22 119.4(3) . . ?
C18 C23 C24 120.5(3) . . ?
C22 C23 C24 120.0(3) . . ?
O3 C24 C25 103.9(2) . . ?
O3 C24 C23 110.1(2) . . ?
C25 C24 C23 114.2(2) . . ?
O3 C24 C34 105.2(2) . . ?
C25 C24 C34 112.4(3) . . ?
C23 C24 C34 110.4(2) . . ?
C26 C25 C24 110.7(3) . . ?
C26 C25 H25 124.6 . . ?
C24 C25 H25 124.6 . . ?
C25 C26 C27 106.6(3) . . ?
C25 C26 C28 129.5(3) . . ?
C27 C26 C28 123.7(3) . . ?
N2 C27 O3 123.6(3) . . ?
N2 C27 C26 125.9(3) . . ?
O3 C27 C26 110.3(2) . . ?
C29 C28 C33 118.6(3) . . ?
C29 C28 C26 120.5(3) . . ?
C33 C28 C26 121.0(3) . . ?
C30 C29 C28 120.4(3) . . ?
C30 C29 H29 119.8 . . ?
C28 C29 H29 119.8 . . ?
C29 C30 C31 120.5(3) . . ?
C29 C30 H30 119.8 . . ?
C31 C30 H30 119.8 . . ?
C32 C31 C30 119.7(3) . . ?
C32 C31 H31 120.2 . . ?
C30 C31 H31 120.2 . . ?
C31 C32 C33 120.4(3) . . ?
C31 C32 H32 119.8 . . ?
C33 C32 H32 119.8 . . ?
C32 C33 C28 120.5(3) . . ?
C32 C33 H33 119.7 . . ?
C28 C33 H33 119.7 . . ?
F5 C34 F7 107.8(3) . . ?
F5 C34 F6 107.6(3) . . ?
F7 C34 F6 107.3(3) . . ?
F5 C34 C24 111.5(3) . . ?
F7 C34 C24 110.7(3) . . ?
F6 C34 C24 111.8(3) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.295
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.060
####################################################################### 
# 
# 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_m12m
_database_code_depnum_ccdc_archive 'CCDC 1490162'
_audit_update_record             
;
2016-07-05 deposited with the CCDC.
2016-10-27 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT029_m12m                
;
PROBLEM: _diffrn_measured_fraction_theta_full value Low .      0.900 Note
RESPONSE: weak diffraction from high angle relections
;
# Added during the CSD deposition process: Tuesday 05 July 2016 07:57 AM
# end Validation Reply Form


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H9 Cl F3 N O2 S'
_chemical_formula_weight         359.74

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'
S S 0.1246 0.1234 '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'
F F 0.0171 0.0103 '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                   6.8042(8)
_cell_length_b                   10.4803(13)
_cell_length_c                   10.7532(13)
_cell_angle_alpha                94.479(2)
_cell_angle_beta                 93.483(2)
_cell_angle_gamma                102.530(2)
_cell_volume                     743.88(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    1795
_cell_measurement_theta_min      2.63
_cell_measurement_theta_max      27.73

_exptl_crystal_description       PLATES
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.606
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             364
_exptl_absorpt_coefficient_mu    0.437
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.9494
_exptl_absorpt_correction_T_max  0.9913
_exptl_absorpt_process_details   'BRUKER SADABS'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(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 SMART APEX CCD IFFRACTOMETER'
_diffrn_measurement_method       'OMEGA-PHI SCAN'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            2838
_diffrn_reflns_av_R_equivalents  0.0169
_diffrn_reflns_av_sigmaI/netI    0.0338
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.91
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2358
_reflns_number_gt                2091
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'BRUKER SMART'
_computing_cell_refinement       'BRUKER SMART'
_computing_data_reduction        'BRUKER SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ORTEP
_computing_publication_material  ?

_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)+(0.1082P)²+0.3315P] 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         2358
_refine_ls_number_parameters     209
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0530
_refine_ls_R_factor_gt           0.0484
_refine_ls_wR_factor_ref         0.1673
_refine_ls_wR_factor_gt          0.1621
_refine_ls_goodness_of_fit_ref   1.185
_refine_ls_restrained_S_all      1.185
_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 0.27995(12) -0.12537(8) 0.41551(8) 0.0293(3) Uani 1 1 d . . .
Cl1 Cl -0.27836(14) 0.68127(8) 0.08557(8) 0.0405(3) Uani 1 1 d . . .
F3 F 0.4342(3) 0.11753(17) 0.08119(17) 0.0330(5) Uani 1 1 d . . .
O1 O 0.3879(3) 0.16888(18) 0.33208(18) 0.0207(5) Uani 1 1 d . . .
F2 F 0.5020(3) -0.03220(19) 0.19077(18) 0.0342(5) Uani 1 1 d . . .
F1 F 0.2257(3) -0.07049(18) 0.07017(16) 0.0321(5) Uani 1 1 d . . .
N1 N 0.4184(4) 0.3885(2) 0.4011(2) 0.0221(6) Uani 1 1 d . . .
O2 O 0.5828(3) 0.3663(2) 0.4756(2) 0.0283(5) Uani 1 1 d . . .
H2 H 0.6240 0.4290 0.5281 0.042 Uiso 1 1 calc R . .
C9 C 0.2360(4) 0.0709(3) 0.2540(3) 0.0204(6) Uani 1 1 d . . .
C15 C 0.3527(4) 0.0206(3) 0.1491(3) 0.0232(7) Uani 1 1 d . . .
C3 C -0.1525(5) 0.5653(3) 0.1376(3) 0.0264(7) Uani 1 1 d . . .
C10 C 0.0937(4) 0.1459(3) 0.2026(3) 0.0208(6) Uani 1 1 d . . .
H10 H -0.0185 0.1098 0.1472 0.025 Uiso 1 1 calc R . .
C11 C 0.1420(4) -0.0391(3) 0.3284(3) 0.0211(6) Uani 1 1 d . . .
C7 C 0.1476(4) 0.2717(3) 0.2463(3) 0.0207(6) Uani 1 1 d . . .
C8 C 0.3293(4) 0.2854(3) 0.3314(3) 0.0198(6) Uani 1 1 d . . .
C12 C -0.0633(5) -0.0844(3) 0.3352(3) 0.0246(7) Uani 1 1 d . . .
H12 H -0.1622 -0.0497 0.2953 0.030 Uiso 1 1 calc R . .
C6 C 0.0461(4) 0.3775(3) 0.2156(3) 0.0204(6) Uani 1 1 d . . .
C13 C -0.1043(5) -0.1912(3) 0.4110(3) 0.0294(7) Uani 1 1 d . . .
H13 H -0.2340 -0.2348 0.4255 0.035 Uiso 1 1 calc R . .
C1 C 0.1524(5) 0.5050(3) 0.2041(3) 0.0255(7) Uani 1 1 d . . .
H1 H 0.2915 0.5271 0.2231 0.031 Uiso 1 1 calc R . .
C2 C 0.0551(5) 0.5982(3) 0.1652(3) 0.0300(7) Uani 1 1 d . . .
H2A H 0.1278 0.6828 0.1573 0.036 Uiso 1 1 calc R . .
C4 C -0.2630(5) 0.4402(3) 0.1505(3) 0.0309(7) Uani 1 1 d . . .
H4 H -0.4024 0.4189 0.1327 0.037 Uiso 1 1 calc R . .
C14 C 0.0644(5) -0.2225(3) 0.4596(3) 0.0297(7) Uani 1 1 d . . .
H14 H 0.0637 -0.2896 0.5114 0.036 Uiso 1 1 calc R . .
C5 C -0.1629(5) 0.3476(3) 0.1902(3) 0.0272(7) Uani 1 1 d . . .
H5 H -0.2362 0.2637 0.2002 0.033 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 C14 1.710(3) . ?
S1 C11 1.723(3) . ?
Cl1 C3 1.739(3) . ?
F3 C15 1.339(3) . ?
O1 C8 1.364(4) . ?
O1 C9 1.458(3) . ?
F2 C15 1.329(4) . ?
F1 C15 1.343(3) . ?
N1 C8 1.277(4) . ?
N1 O2 1.407(3) . ?
O2 H2 0.8200 . ?
C9 C10 1.481(4) . ?
C9 C11 1.505(4) . ?
C9 C15 1.543(4) . ?
C3 C4 1.385(5) . ?
C3 C2 1.387(5) . ?
C10 C7 1.328(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.383(4) . ?
C7 C8 1.467(4) . ?
C7 C6 1.476(4) . ?
C12 C13 1.425(5) . ?
C12 H12 0.9300 . ?
C6 C1 1.393(4) . ?
C6 C5 1.393(4) . ?
C13 C14 1.347(5) . ?
C13 H13 0.9300 . ?
C1 C2 1.370(5) . ?
C1 H1 0.9300 . ?
C2 H2A 0.9300 . ?
C4 C5 1.380(5) . ?
C4 H4 0.9300 . ?
C14 H14 0.9300 . ?
C5 H5 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
C14 S1 C11 91.39(15) . . ?
C8 O1 C9 107.3(2) . . ?
C8 N1 O2 111.5(2) . . ?
N1 O2 H2 109.5 . . ?
O1 C9 C10 104.5(2) . . ?
O1 C9 C11 110.8(2) . . ?
C10 C9 C11 114.8(2) . . ?
O1 C9 C15 104.7(2) . . ?
C10 C9 C15 110.5(2) . . ?
C11 C9 C15 110.9(2) . . ?
F2 C15 F3 107.0(2) . . ?
F2 C15 F1 108.0(2) . . ?
F3 C15 F1 106.8(2) . . ?
F2 C15 C9 113.7(2) . . ?
F3 C15 C9 111.3(2) . . ?
F1 C15 C9 109.8(2) . . ?
C4 C3 C2 120.9(3) . . ?
C4 C3 Cl1 118.8(3) . . ?
C2 C3 Cl1 120.3(2) . . ?
C7 C10 C9 111.0(2) . . ?
C7 C10 H10 124.5 . . ?
C9 C10 H10 124.5 . . ?
C12 C11 C9 124.9(3) . . ?
C12 C11 S1 111.6(2) . . ?
C9 C11 S1 123.5(2) . . ?
C10 C7 C8 106.5(3) . . ?
C10 C7 C6 127.1(3) . . ?
C8 C7 C6 126.4(2) . . ?
N1 C8 O1 123.2(3) . . ?
N1 C8 C7 126.2(3) . . ?
O1 C8 C7 110.6(2) . . ?
C11 C12 C13 111.4(3) . . ?
C11 C12 H12 124.3 . . ?
C13 C12 H12 124.3 . . ?
C1 C6 C5 118.5(3) . . ?
C1 C6 C7 122.4(3) . . ?
C5 C6 C7 118.9(3) . . ?
C14 C13 C12 113.0(3) . . ?
C14 C13 H13 123.5 . . ?
C12 C13 H13 123.5 . . ?
C2 C1 C6 121.0(3) . . ?
C2 C1 H1 119.5 . . ?
C6 C1 H1 119.5 . . ?
C1 C2 C3 119.5(3) . . ?
C1 C2 H2A 120.2 . . ?
C3 C2 H2A 120.2 . . ?
C5 C4 C3 118.9(3) . . ?
C5 C4 H4 120.6 . . ?
C3 C4 H4 120.6 . . ?
C13 C14 S1 112.6(3) . . ?
C13 C14 H14 123.7 . . ?
S1 C14 H14 123.7 . . ?
C4 C5 C6 121.2(3) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 H5 119.4 . . ?

_diffrn_measured_fraction_theta_max 0.900
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.900
_refine_diff_density_max         0.528
_refine_diff_density_min         -0.397
_refine_diff_density_rms         0.097
