# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_a
_database_code_depnum_ccdc_archive 'CCDC 1545029'
#Added by publCIF



_audit_update_record             
;
2017-04-20 deposited with the CCDC.
2018-10-11 downloaded from the CCDC.
;


_diffrn_radiation_monochromator  No
_audit_creation_date             2017-04-19
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.28 svn.r3405 for OlexSys, GUI svn.r5335)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        
;\
2,2,2-trifluoro-1-[1-phenyl-3-(2-phenylethynyl)-3-(trifluoromethyl)-3H,4aH-[1,\
3]oxazino[3,2-a]quinolin-2-yl]-1-ethanone
;

_chemical_formula_moiety         'C29 H17 F6 N O2'
_chemical_formula_sum            'C29 H17 F6 N O2'
_chemical_formula_weight         525.43
_chemical_absolute_configuration syn
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0030 0.0020 '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 0.0170 0.0100 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0060 0.0030 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0110 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   9.2784(4)
_cell_length_b                   14.1722(6)
_cell_length_c                   9.8379(4)
_cell_angle_alpha                90
_cell_angle_beta                 114.0770(10)
_cell_angle_gamma                90
_cell_volume                     1181.09(9)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    781
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      30.3
_cell_measurement_theta_min      2.4
_shelx_estimated_absorpt_T_max   0.940
_shelx_estimated_absorpt_T_min   0.940
_exptl_absorpt_coefficient_mu    0.125
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.5341
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2014/4 (Bruker,2014/4) was used for absorption correction.
wR2(int) was 0.1252 before and 0.0506 after correction.
The Ratio of minimum to maximum transmission is 0.7159.
The λ/2 correction factor is Not present.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.477
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       'pale, cyllinder-like'
_exptl_crystal_F_000             536
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.5
_exptl_crystal_size_min          0.5
_exptl_special_details           ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0358
_diffrn_reflns_av_unetI/netI     0.0368
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.926
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            38293
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.903
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.907
_diffrn_reflns_theta_min         2.267
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.926
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       "φ and ω scans'"
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   IuS
_reflns_Friedel_coverage         0.883
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.879
_reflns_number_gt                5807
_reflns_number_total             6736
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.271
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.047
_refine_ls_abs_structure_details 
;
 Flack x determined using 2485 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.07(16)
_refine_ls_extinction_coef       0.022(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     412
_refine_ls_number_reflns         6736
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0510
_refine_ls_R_factor_gt           0.0366
_refine_ls_restrained_S_all      1.023
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0347P)²+0.2245P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0701
_refine_ls_wR_factor_ref         0.0746
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_special_details      
;
The structure was solved using Direct Methods (ShelXS). RE = 0.2, Nqual =  -1, Ralpha = 0.042
;
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 -0.11087(18) 0.08661(10) -0.20150(13) 0.0340(3) Uani 1 1 d . . . . .
F2 F -0.16336(17) 0.05979(9) -0.01214(16) 0.0312(3) Uani 1 1 d . . . . .
F3 F 0.05138(17) 0.00785(10) -0.01512(17) 0.0359(4) Uani 1 1 d . . . . .
F4 F 0.15125(15) 0.39374(8) 0.28176(14) 0.0247(3) Uani 1 1 d . . . . .
F5 F 0.38972(14) 0.34552(9) 0.40429(14) 0.0261(3) Uani 1 1 d . . . . .
F6 F 0.28840(16) 0.34411(10) 0.16480(14) 0.0281(3) Uani 1 1 d . . . . .
O1 O 0.17461(15) 0.22717(10) 0.42363(14) 0.0155(3) Uani 1 1 d . . . . .
O2 O 0.14083(17) 0.19405(12) -0.03464(16) 0.0254(3) Uani 1 1 d . . . . .
N1 N -0.09958(18) 0.25359(11) 0.29569(16) 0.0127(3) Uani 1 1 d . . . . .
C1 C -0.2893(3) 0.48817(15) 0.4291(2) 0.0214(4) Uani 1 1 d . . . . .
H1 H -0.331(3) 0.5417(19) 0.464(3) 0.027(7) Uiso 1 1 d . . . . .
C2 C -0.2183(2) 0.41518(15) 0.5269(2) 0.0181(4) Uani 1 1 d . . . . .
H2 H -0.211(3) 0.4196(17) 0.625(3) 0.014(5) Uiso 1 1 d . . . . .
C3 C -0.1536(2) 0.33737(14) 0.4840(2) 0.0147(4) Uani 1 1 d . . . . .
C4 C -0.1624(2) 0.33404(13) 0.3376(2) 0.0130(4) Uani 1 1 d . . . . .
C5 C -0.1002(2) 0.24071(13) 0.15480(19) 0.0121(4) Uani 1 1 d . . . . .
C6 C 0.0377(2) 0.21266(13) 0.1501(2) 0.0127(4) Uani 1 1 d . . . . .
C7 C 0.1947(2) 0.22828(13) 0.2864(2) 0.0136(4) Uani 1 1 d . . . . .
C8 C 0.3160(2) 0.15997(14) 0.2920(2) 0.0164(4) Uani 1 1 d . . . . .
C9 C 0.4153(2) 0.10699(14) 0.2903(2) 0.0170(4) Uani 1 1 d . . . . .
C10 C 0.5335(2) 0.04675(14) 0.2771(2) 0.0165(4) Uani 1 1 d . . . . .
C11 C 0.5065(3) 0.00845(15) 0.1380(2) 0.0194(4) Uani 1 1 d . . . . .
H11 H 0.403(3) 0.0217(19) 0.055(3) 0.031(7) Uiso 1 1 d . . . . .
C12 C 0.6231(3) -0.04409(15) 0.1191(3) 0.0243(5) Uani 1 1 d . . . . .
H12 H 0.602(3) -0.070(2) 0.021(3) 0.033(7) Uiso 1 1 d . . . . .
C13 C 0.7657(3) -0.05978(16) 0.2396(3) 0.0276(5) Uani 1 1 d . . . . .
H13 H 0.845(3) -0.100(2) 0.226(3) 0.039(8) Uiso 1 1 d . . . . .
C14 C -0.0705(2) 0.26273(14) 0.5874(2) 0.0171(4) Uani 1 1 d . . . . .
H14 H -0.074(3) 0.2620(16) 0.686(3) 0.016(6) Uiso 1 1 d . . . . .
C15 C 0.0130(2) 0.19756(14) 0.5541(2) 0.0168(4) Uani 1 1 d . . . . .
H15 H 0.075(3) 0.1494(17) 0.623(3) 0.017(6) Uiso 1 1 d . . . . .
C16 C 0.0197(2) 0.19553(14) 0.4055(2) 0.0139(4) Uani 1 1 d . . . . .
H16 H 0.005(2) 0.1326(16) 0.367(2) 0.009(5) Uiso 1 1 d . . . . .
C17 C -0.2285(2) 0.40929(14) 0.2414(2) 0.0165(4) Uani 1 1 d . . . . .
H17 H -0.231(3) 0.4086(18) 0.139(3) 0.027(7) Uiso 1 1 d . . . . .
C18 C -0.2928(3) 0.48491(14) 0.2869(2) 0.0201(4) Uani 1 1 d . . . . .
H18 H -0.345(3) 0.5347(17) 0.217(3) 0.019(6) Uiso 1 1 d . . . . .
C19 C -0.2497(2) 0.24904(13) 0.0222(2) 0.0128(4) Uani 1 1 d . . . . .
C20 C -0.3911(2) 0.22123(14) 0.0285(2) 0.0149(4) Uani 1 1 d . . . . .
H20 H -0.391(3) 0.1992(16) 0.120(3) 0.011(5) Uiso 1 1 d . . . . .
C21 C -0.5298(2) 0.22134(14) -0.1005(2) 0.0186(4) Uani 1 1 d . . . . .
H21 H -0.625(3) 0.2054(17) -0.095(3) 0.018(6) Uiso 1 1 d . . . . .
C22 C -0.5279(2) 0.24846(16) -0.2352(2) 0.0208(4) Uani 1 1 d . . . . .
H22 H -0.620(3) 0.246(2) -0.320(3) 0.026(6) Uiso 1 1 d . . . . .
C23 C -0.3895(2) 0.27855(16) -0.2416(2) 0.0193(4) Uani 1 1 d . . . . .
H23 H -0.387(3) 0.3000(19) -0.332(3) 0.026(6) Uiso 1 1 d . . . . .
C24 C -0.2501(2) 0.28018(14) -0.1129(2) 0.0153(4) Uani 1 1 d . . . . .
H24 H -0.153(3) 0.3062(15) -0.118(2) 0.008(5) Uiso 1 1 d . . . . .
C25 C 0.0481(2) 0.17068(14) 0.0170(2) 0.0157(4) Uani 1 1 d . . . . .
C26 C -0.0491(2) 0.08076(15) -0.0543(2) 0.0199(4) Uani 1 1 d . . . . .
C27 C 0.2572(2) 0.32939(15) 0.2836(2) 0.0179(4) Uani 1 1 d . . . . .
C28 C 0.7918(3) -0.02405(17) 0.3782(3) 0.0268(5) Uani 1 1 d . . . . .
H28 H 0.889(3) -0.0342(19) 0.459(3) 0.027(7) Uiso 1 1 d . . . . .
C29 C 0.6767(3) 0.02980(16) 0.3981(3) 0.0224(4) Uani 1 1 d . . . . .
H29 H 0.691(3) 0.0549(18) 0.490(3) 0.022(6) Uiso 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 C26 1.325(2) . ?
F2 C26 1.320(2) . ?
F3 C26 1.339(2) . ?
F4 C27 1.336(2) . ?
F5 C27 1.335(2) . ?
F6 C27 1.330(2) . ?
O1 C7 1.437(2) . ?
O1 C16 1.446(2) . ?
O2 C25 1.210(2) . ?
N1 C4 1.416(2) . ?
N1 C5 1.396(2) . ?
N1 C16 1.447(2) . ?
C1 C2 1.383(3) . ?
C1 C18 1.387(3) . ?
C2 C3 1.400(3) . ?
C3 C4 1.410(2) . ?
C3 C14 1.452(3) . ?
C4 C17 1.391(3) . ?
C5 C6 1.359(3) . ?
C5 C19 1.471(2) . ?
C6 C7 1.541(2) . ?
C6 C25 1.477(3) . ?
C7 C8 1.469(3) . ?
C7 C27 1.550(3) . ?
C8 C9 1.193(3) . ?
C9 C10 1.437(3) . ?
C10 C11 1.397(3) . ?
C10 C29 1.396(3) . ?
C11 C12 1.386(3) . ?
C12 C13 1.387(3) . ?
C13 C28 1.380(4) . ?
C14 C15 1.330(3) . ?
C15 C16 1.488(3) . ?
C17 C18 1.387(3) . ?
C19 C20 1.395(3) . ?
C19 C24 1.399(3) . ?
C20 C21 1.391(3) . ?
C21 C22 1.387(3) . ?
C22 C23 1.379(3) . ?
C23 C24 1.393(3) . ?
C25 C26 1.553(3) . ?
C28 C29 1.390(3) . ?

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 C16 113.06(14) . . ?
C4 N1 C16 121.38(15) . . ?
C5 N1 C4 123.97(15) . . ?
C5 N1 C16 111.07(15) . . ?
C2 C1 C18 119.02(19) . . ?
C1 C2 C3 121.38(18) . . ?
C2 C3 C4 118.74(18) . . ?
C2 C3 C14 122.19(17) . . ?
C4 C3 C14 118.98(17) . . ?
C3 C4 N1 117.71(16) . . ?
C17 C4 N1 122.61(16) . . ?
C17 C4 C3 119.66(17) . . ?
N1 C5 C19 119.39(16) . . ?
C6 C5 N1 116.73(16) . . ?
C6 C5 C19 123.61(16) . . ?
C5 C6 C7 119.82(16) . . ?
C5 C6 C25 123.44(16) . . ?
C25 C6 C7 116.69(15) . . ?
O1 C7 C6 112.15(15) . . ?
O1 C7 C8 110.42(15) . . ?
O1 C7 C27 102.68(14) . . ?
C6 C7 C27 110.17(15) . . ?
C8 C7 C6 112.08(16) . . ?
C8 C7 C27 108.89(15) . . ?
C9 C8 C7 176.5(2) . . ?
C8 C9 C10 175.3(2) . . ?
C11 C10 C9 118.76(18) . . ?
C29 C10 C9 121.4(2) . . ?
C29 C10 C11 119.75(19) . . ?
C12 C11 C10 120.2(2) . . ?
C11 C12 C13 119.7(2) . . ?
C28 C13 C12 120.5(2) . . ?
C15 C14 C3 121.95(18) . . ?
C14 C15 C16 121.17(18) . . ?
O1 C16 N1 109.54(15) . . ?
O1 C16 C15 108.12(15) . . ?
N1 C16 C15 113.39(16) . . ?
C18 C17 C4 120.08(18) . . ?
C17 C18 C1 121.03(19) . . ?
C20 C19 C5 120.10(16) . . ?
C20 C19 C24 119.55(17) . . ?
C24 C19 C5 120.27(16) . . ?
C21 C20 C19 119.73(18) . . ?
C22 C21 C20 120.32(19) . . ?
C23 C22 C21 120.28(19) . . ?
C22 C23 C24 120.04(19) . . ?
C23 C24 C19 119.98(18) . . ?
O2 C25 C6 125.19(18) . . ?
O2 C25 C26 114.60(17) . . ?
C6 C25 C26 119.68(16) . . ?
F1 C26 F3 107.63(16) . . ?
F1 C26 C25 110.77(16) . . ?
F2 C26 F1 108.21(17) . . ?
F2 C26 F3 106.86(17) . . ?
F2 C26 C25 115.82(16) . . ?
F3 C26 C25 107.20(16) . . ?
F4 C27 C7 110.68(16) . . ?
F5 C27 F4 107.51(16) . . ?
F5 C27 C7 110.97(16) . . ?
F6 C27 F4 107.70(16) . . ?
F6 C27 F5 107.62(16) . . ?
F6 C27 C7 112.17(16) . . ?
C13 C28 C29 120.3(2) . . ?
C28 C29 C10 119.5(2) . . ?

_olex2_submission_special_instructions 'No special instructions were received'

