# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_1665a
_database_code_depnum_ccdc_archive 'CCDC 1491776'
_audit_update_record             
;
2016-07-09 deposited with the CCDC.
2016-09-19 downloaded from the CCDC.
;

#==============================================================================
# CHEMICAL DATA

_chemical_formula_sum            'C16 H12 F3 N O2'
_chemical_formula_moiety         'C16 H12 F3 N O2'
_chemical_formula_weight         307.27
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
_space_group_IT_number           14
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,1/2+Y,1/2-Z
3 -X,-Y,-Z
4 +X,-1/2-Y,-1/2+Z
#------------------------------------------------------------------------------
_cell_length_a                   12.057(4)
_cell_length_b                   8.771(2)
_cell_length_c                   14.736(5)
_cell_angle_alpha                90.0000
_cell_angle_beta                 113.287(5)
_cell_angle_gamma                90.0000
_cell_volume                     1431.4(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3280
_cell_measurement_theta_min      2.80
_cell_measurement_theta_max      27.50
_cell_measurement_temperature    93
#------------------------------------------------------------------------------
_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.040
_exptl_crystal_density_diffrn    1.426
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             632.00
_exptl_absorpt_coefficient_mu    0.120
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'REQAB (Rigaku, 1998)'
_exptl_absorpt_correction_T_min  0.881
_exptl_absorpt_correction_T_max  0.995

#==============================================================================
# EXPERIMENTAL DATA

_diffrn_ambient_temperature      93
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku Saturn724+'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 7.111
_diffrn_reflns_number            11584
_diffrn_reflns_av_R_equivalents  0.0548
_diffrn_reflns_theta_max         27.480
_diffrn_reflns_theta_min         2.767
_diffrn_reflns_theta_full        27.480
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.000
_diffrn_reflns_Laue_measured_fraction_full 0.000
_diffrn_reflns_point_group_measured_fraction_max 0.000
_diffrn_reflns_point_group_measured_fraction_full 0.000
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       17
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             3283
_reflns_number_gt                2305
_reflns_threshold_expression     F²>2.0σ(F²)

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.0921
_refine_ls_R_factor_gt           0.0578
_refine_ls_wR_factor_ref         0.1121
_refine_ls_wR_factor_gt          0.0995
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         3283
_refine_ls_number_parameters     199
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0389P)²+0.5104P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.34
_refine_diff_density_min         -0.28
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
F F 0.0171 0.0103
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL PARAMETERS

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 0.00794(12) 0.00769(17) 0.59878(9) 0.0401(4) Uani 1 1 d . . .
F2 F 0.18800(14) -0.05248(17) 0.61667(10) 0.0447(4) Uani 1 1 d . . .
F3 F 0.14680(13) 0.17583(15) 0.64311(9) 0.0395(4) Uani 1 1 d . . .
O1 O 0.14779(12) -0.15783(15) 0.88589(9) 0.0192(3) Uani 1 1 d . . .
O2 O 0.05778(13) -0.25919(16) 0.73420(10) 0.0263(4) Uani 1 1 d . . .
N1 N 0.4820(2) 0.7624(2) 0.85990(15) 0.0452(6) Uani 1 1 d . . .
C1 C 0.15016(19) 0.0568(2) 0.98982(15) 0.0218(5) Uani 1 1 d . . .
H1A H 0.0614 0.0576 0.9528 0.026 Uiso 1 1 calc R . .
H1B H 0.1788 0.1626 1.0083 0.026 Uiso 1 1 calc R . .
C2 C 0.1869(2) -0.0461(3) 1.08104(16) 0.0255(5) Uani 1 1 d . . .
H2A H 0.1807 0.0090 1.1375 0.031 Uiso 1 1 calc R . .
H2B H 0.1353 -0.1382 1.0670 0.031 Uiso 1 1 calc R . .
C3 C 0.3179(2) -0.0885(3) 1.10277(16) 0.0328(6) Uani 1 1 d . . .
H3A H 0.3329 -0.1968 1.1228 0.039 Uiso 1 1 calc R . .
H3B H 0.3737 -0.0244 1.1569 0.039 Uiso 1 1 calc R . .
C4 C 0.33785(18) -0.0611(2) 1.00707(14) 0.0187(4) Uani 1 1 d . . .
H4A H 0.3965 0.0225 1.0161 0.022 Uiso 1 1 calc R . .
H4B H 0.3684 -0.1545 0.9871 0.022 Uiso 1 1 calc R . .
C5 C 0.21334(17) -0.0178(2) 0.92963(14) 0.0157(4) Uani 1 1 d . . .
C6 C 0.21300(17) 0.0702(2) 0.84180(14) 0.0154(4) Uani 1 1 d . . .
C7 C 0.15326(17) -0.0094(2) 0.75982(14) 0.0168(4) Uani 1 1 d . . .
C8 C 0.11207(18) -0.1553(2) 0.78642(14) 0.0187(5) Uani 1 1 d . . .
C9 C 0.1242(2) 0.0310(2) 0.65533(15) 0.0246(5) Uani 1 1 d . . .
C10 C 0.27443(18) 0.2194(2) 0.85184(14) 0.0163(4) Uani 1 1 d . . .
C11 C 0.22770(18) 0.3502(2) 0.87753(14) 0.0191(5) Uani 1 1 d . . .
H11 H 0.1571 0.3433 0.8911 0.023 Uiso 1 1 calc R . .
C12 C 0.28325(19) 0.4893(2) 0.88329(15) 0.0216(5) Uani 1 1 d . . .
H12 H 0.2509 0.5783 0.9004 0.026 Uiso 1 1 calc R . .
C13 C 0.38713(19) 0.4988(2) 0.86385(14) 0.0206(5) Uani 1 1 d . . .
C14 C 0.43548(19) 0.3692(2) 0.83963(15) 0.0232(5) Uani 1 1 d . . .
H14 H 0.5067 0.3761 0.8269 0.028 Uiso 1 1 calc R . .
C15 C 0.37924(19) 0.2295(2) 0.83406(15) 0.0210(5) Uani 1 1 d . . .
H15 H 0.4124 0.1404 0.8180 0.025 Uiso 1 1 calc R . .
C16 C 0.4414(2) 0.6457(3) 0.86303(16) 0.0298(6) Uani 1 1 d . . .


#==============================================================================
_computing_data_collection       'CrystalClear-SM Expert 2.0 r16 (Rigaku, 2014)'
_computing_cell_refinement       'CrystalClear-SM Expert 2.0 r16'
_computing_data_reduction        'CrystalClear-SM Expert 2.0 r16'
_computing_structure_solution    'Il Milione (Burla, et al., 2007)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2 (Rigaku, 2015)'
_computing_molecular_graphics    'CrystalStructure 4.2'

#==============================================================================
# MOLECULAR GEOMETRY

_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 1.334(2) . ?
F2 C9 1.341(3) . ?
F3 C9 1.326(2) . ?
O1 C8 1.355(2) . ?
O1 C5 1.465(2) . ?
O2 C8 1.205(2) . ?
N1 C16 1.143(3) . ?
C1 C5 1.526(3) . ?
C1 C2 1.532(3) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.528(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.540(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.531(3) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.505(3) . ?
C6 C7 1.333(3) . ?
C6 C10 1.482(3) . ?
C7 C9 1.481(3) . ?
C7 C8 1.481(3) . ?
C10 C15 1.391(3) . ?
C10 C11 1.395(3) . ?
C11 C12 1.378(3) . ?
C11 H11 0.9500 . ?
C12 C13 1.393(3) . ?
C12 H12 0.9500 . ?
C13 C14 1.387(3) . ?
C13 C16 1.448(3) . ?
C14 C15 1.387(3) . ?
C14 H14 0.9500 . ?
C15 H15 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 C5 110.36(15) . . ?
C5 C1 C2 102.69(17) . . ?
C5 C1 H1A 111.2 . . ?
C2 C1 H1A 111.2 . . ?
C5 C1 H1B 111.2 . . ?
C2 C1 H1B 111.2 . . ?
H1A C1 H1B 109.1 . . ?
C3 C2 C1 104.09(17) . . ?
C3 C2 H2A 110.9 . . ?
C1 C2 H2A 110.9 . . ?
C3 C2 H2B 110.9 . . ?
C1 C2 H2B 110.9 . . ?
H2A C2 H2B 109.0 . . ?
C2 C3 C4 107.02(17) . . ?
C2 C3 H3A 110.3 . . ?
C4 C3 H3A 110.3 . . ?
C2 C3 H3B 110.3 . . ?
C4 C3 H3B 110.3 . . ?
H3A C3 H3B 108.6 . . ?
C5 C4 C3 105.02(17) . . ?
C5 C4 H4A 110.7 . . ?
C3 C4 H4A 110.7 . . ?
C5 C4 H4B 110.7 . . ?
C3 C4 H4B 110.7 . . ?
H4A C4 H4B 108.8 . . ?
O1 C5 C6 103.52(14) . . ?
O1 C5 C1 107.98(16) . . ?
C6 C5 C1 116.59(16) . . ?
O1 C5 C4 108.64(15) . . ?
C6 C5 C4 115.87(16) . . ?
C1 C5 C4 103.92(16) . . ?
C7 C6 C10 128.48(18) . . ?
C7 C6 C5 109.14(17) . . ?
C10 C6 C5 122.37(16) . . ?
C6 C7 C9 129.64(19) . . ?
C6 C7 C8 109.27(17) . . ?
C9 C7 C8 121.07(17) . . ?
O2 C8 O1 122.60(19) . . ?
O2 C8 C7 129.70(19) . . ?
O1 C8 C7 107.69(16) . . ?
F3 C9 F1 106.49(18) . . ?
F3 C9 F2 106.41(18) . . ?
F1 C9 F2 106.75(17) . . ?
F3 C9 C7 113.19(17) . . ?
F1 C9 C7 111.78(18) . . ?
F2 C9 C7 111.80(18) . . ?
C15 C10 C11 119.54(19) . . ?
C15 C10 C6 119.52(18) . . ?
C11 C10 C6 120.93(18) . . ?
C12 C11 C10 120.4(2) . . ?
C12 C11 H11 119.8 . . ?
C10 C11 H11 119.8 . . ?
C11 C12 C13 119.6(2) . . ?
C11 C12 H12 120.2 . . ?
C13 C12 H12 120.2 . . ?
C14 C13 C12 120.52(19) . . ?
C14 C13 C16 119.4(2) . . ?
C12 C13 C16 120.0(2) . . ?
C13 C14 C15 119.6(2) . . ?
C13 C14 H14 120.2 . . ?
C15 C14 H14 120.2 . . ?
C14 C15 C10 120.3(2) . . ?
C14 C15 H15 119.9 . . ?
C10 C15 H15 119.9 . . ?
N1 C16 C13 178.2(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
C5 C1 C2 C3 37.8(2) . . . . ?
C1 C2 C3 C4 -20.1(2) . . . . ?
C2 C3 C4 C5 -5.2(2) . . . . ?
C8 O1 C5 C6 -0.38(19) . . . . ?
C8 O1 C5 C1 123.82(17) . . . . ?
C8 O1 C5 C4 -124.07(17) . . . . ?
C2 C1 C5 O1 73.91(19) . . . . ?
C2 C1 C5 C6 -170.16(17) . . . . ?
C2 C1 C5 C4 -41.3(2) . . . . ?
C3 C4 C5 O1 -86.04(19) . . . . ?
C3 C4 C5 C6 157.99(17) . . . . ?
C3 C4 C5 C1 28.7(2) . . . . ?
O1 C5 C6 C7 0.9(2) . . . . ?
C1 C5 C6 C7 -117.4(2) . . . . ?
C4 C5 C6 C7 119.76(19) . . . . ?
O1 C5 C6 C10 -177.67(16) . . . . ?
C1 C5 C6 C10 64.0(2) . . . . ?
C4 C5 C6 C10 -58.9(2) . . . . ?
C10 C6 C7 C9 -4.2(4) . . . . ?
C5 C6 C7 C9 177.3(2) . . . . ?
C10 C6 C7 C8 177.37(19) . . . . ?
C5 C6 C7 C8 -1.1(2) . . . . ?
C5 O1 C8 O2 179.02(18) . . . . ?
C5 O1 C8 C7 -0.3(2) . . . . ?
C6 C7 C8 O2 -178.3(2) . . . . ?
C9 C7 C8 O2 3.1(3) . . . . ?
C6 C7 C8 O1 0.9(2) . . . . ?
C9 C7 C8 O1 -177.69(18) . . . . ?
C6 C7 C9 F3 -10.6(3) . . . . ?
C8 C7 C9 F3 167.63(18) . . . . ?
C6 C7 C9 F1 -130.9(2) . . . . ?
C8 C7 C9 F1 47.4(3) . . . . ?
C6 C7 C9 F2 109.5(2) . . . . ?
C8 C7 C9 F2 -72.2(2) . . . . ?
C7 C6 C10 C15 -69.5(3) . . . . ?
C5 C6 C10 C15 108.8(2) . . . . ?
C7 C6 C10 C11 109.6(2) . . . . ?
C5 C6 C10 C11 -72.1(2) . . . . ?
C15 C10 C11 C12 1.4(3) . . . . ?
C6 C10 C11 C12 -177.73(18) . . . . ?
C10 C11 C12 C13 -0.4(3) . . . . ?
C11 C12 C13 C14 -0.6(3) . . . . ?
C11 C12 C13 C16 175.74(19) . . . . ?
C12 C13 C14 C15 0.5(3) . . . . ?
C16 C13 C14 C15 -175.84(19) . . . . ?
C13 C14 C15 C10 0.5(3) . . . . ?
C11 C10 C15 C14 -1.4(3) . . . . ?
C6 C10 C15 C14 177.67(18) . . . . ?
C14 C13 C16 N1 95(9) . . . . ?
C12 C13 C16 N1 -81(9) . . . . ?

#==============================================================================

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.

#==============================================================================
#     End of CIF
#==============================================================================
_chemical_name_systematic        
4-(2-Oxo-3-(trifluoromethyl)-1-oxaspiro[4.4]non-3-en-4-yl)benzonitrile
