# Electronic Supplementary Material (ESI) for ChemComm.
# 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. 
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data_mo_151111_0m
_database_code_depnum_ccdc_archive 'CCDC 1470637'
_audit_update_record             
;
2016-03-25 deposited with the CCDC.
2016-06-03 downloaded from the CCDC.
;
_audit_creation_date             2015-11-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.09.30 svn.r3233 for OlexSys, GUI svn.r5103)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H14 F3 N3 O2'
_chemical_formula_sum            'C16 H14 F3 N3 O2'
_chemical_formula_weight         337.30
_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 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.013(2)
_cell_length_b                   7.5562(16)
_cell_length_c                   21.159(5)
_cell_angle_alpha                90
_cell_angle_beta                 93.102(3)
_cell_angle_gamma                90
_cell_volume                     1598.5(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3909
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      26.78
_cell_measurement_theta_min      2.73
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.118
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6382
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.1120 before and 0.0534 after correction.
The Ratio of minimum to maximum transmission is 0.8561.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.402
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             696
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0294
_diffrn_reflns_av_unetI/netI     0.0301
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            12841
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        25.250
_diffrn_reflns_theta_max         27.479
_diffrn_reflns_theta_min         2.037
_diffrn_ambient_temperature      100.01(10)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2429
_reflns_number_total             3610
_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       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_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         0.302
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.036
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     217
_refine_ls_number_reflns         3610
_refine_ls_number_restraints     12
_refine_ls_R_factor_all          0.0836
_refine_ls_R_factor_gt           0.0578
_refine_ls_restrained_S_all      1.085
_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)+(0.0762P)²+0.6387P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1648
_refine_ls_wR_factor_ref         0.1835
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Uiso/Uaniso restraints and constraints
Uanis(C1) \\sim Ueq, Uanis(C6) \\sim Ueq: with sigma of 0.005 and sigma for
terminal atoms of 0.01
3.a Ternary CH refined with riding coordinates:
 C8(H8)
3.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C15(H15A,H15B)
3.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C3(H3), C5(H5), C6(H6), C10(H10), C11(H11), C13(H13), C14(H14)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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 0.06622(18) -0.0622(3) 0.07275(14) 0.1368(9) Uani 1 1 d . . . . .
F2 F 0.2072(2) -0.2626(2) 0.06058(11) 0.1184(7) Uani 1 1 d . . . . .
F3 F 0.1744(3) -0.1652(3) 0.15068(11) 0.1499(10) Uani 1 1 d . . . . .
O1 O -0.45531(18) 0.7110(3) 0.14462(9) 0.0781(5) Uani 1 1 d . . . . .
O2 O -0.4208(2) 0.7131(3) 0.04586(9) 0.0957(7) Uani 1 1 d . . . . .
N1 N 0.16432(18) 0.2797(2) 0.11002(8) 0.0560(5) Uani 1 1 d . . . . .
N2 N 0.10026(18) 0.3252(3) 0.15535(8) 0.0549(5) Uani 1 1 d . . . . .
N3 N -0.3866(2) 0.6788(3) 0.10054(10) 0.0616(5) Uani 1 1 d . . . . .
C1 C 0.7775(3) 0.0468(4) 0.17418(18) 0.0907(9) Uani 1 1 d . U . . .
H1 H 0.8596 -0.0113 0.1853 0.109 Uiso 1 1 calc R . . . .
C2 C 0.7427(3) 0.0794(4) 0.11313(15) 0.0785(8) Uani 1 1 d . . . . .
H2 H 0.8012 0.0467 0.0812 0.094 Uiso 1 1 calc R . . . .
C3 C 0.6225(2) 0.1602(3) 0.09663(11) 0.0619(6) Uani 1 1 d . . . . .
H3 H 0.5986 0.1802 0.0532 0.074 Uiso 1 1 calc R . . . .
C4 C 0.5363(2) 0.2126(3) 0.14140(10) 0.0566(5) Uani 1 1 d . . . . .
C5 C 0.5724(3) 0.1809(4) 0.20429(12) 0.0828(9) Uani 1 1 d . . . . .
H5 H 0.5151 0.2156 0.2364 0.099 Uiso 1 1 calc R . . . .
C6 C 0.6949(4) 0.0970(5) 0.22032(15) 0.0980(11) Uani 1 1 d . U . . .
H6 H 0.7204 0.0750 0.2635 0.118 Uiso 1 1 calc R . . . .
C7 C 0.4051(2) 0.2996(3) 0.12219(12) 0.0625(6) Uani 1 1 d . . . . .
H7A H 0.4073 0.3391 0.0776 0.075 Uiso 1 1 calc R . . . .
H7B H 0.3940 0.4059 0.1487 0.075 Uiso 1 1 calc R . . . .
C8 C 0.2844(2) 0.1774(3) 0.12866(10) 0.0527(5) Uani 1 1 d . . . . .
H8 H 0.2802 0.1379 0.1736 0.063 Uiso 1 1 calc R . . . .
C9 C -0.0191(2) 0.4245(3) 0.13841(9) 0.0498(5) Uani 1 1 d . . . . .
C10 C -0.0655(2) 0.4531(3) 0.07659(10) 0.0599(6) Uani 1 1 d . . . . .
H10 H -0.0149 0.4124 0.0428 0.072 Uiso 1 1 calc R . . . .
C11 C -0.1841(2) 0.5400(3) 0.06386(10) 0.0610(6) Uani 1 1 d . . . . .
H11 H -0.2161 0.5610 0.0214 0.073 Uiso 1 1 calc R . . . .
C12 C -0.2558(2) 0.5959(3) 0.11371(10) 0.0510(5) Uani 1 1 d . . . . .
C13 C -0.2121(3) 0.5696(4) 0.17488(11) 0.0724(7) Uani 1 1 d . . . . .
H13 H -0.2632 0.6096 0.2086 0.087 Uiso 1 1 calc R . . . .
C14 C -0.0914(2) 0.4832(4) 0.18709(11) 0.0715(7) Uani 1 1 d . . . . .
H14 H -0.0588 0.4647 0.2296 0.086 Uiso 1 1 calc R . . . .
C15 C 0.2918(2) 0.0171(3) 0.08563(11) 0.0570(5) Uani 1 1 d . . . . .
H15A H 0.2877 0.0585 0.0412 0.068 Uiso 1 1 calc R . . . .
H15B H 0.3796 -0.0408 0.0940 0.068 Uiso 1 1 calc R . . . .
C16 C 0.1859(3) -0.1162(4) 0.09253(14) 0.0740(7) 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 C16 1.313(3) . ?
F2 C16 1.320(3) . ?
F3 C16 1.296(3) . ?
O1 N3 1.213(2) . ?
O2 N3 1.217(3) . ?
N1 N2 1.231(2) . ?
N1 C8 1.465(3) . ?
N2 C9 1.440(3) . ?
N3 C12 1.465(3) . ?
C1 H1 0.9500 . ?
C1 C2 1.343(4) . ?
C1 C6 1.367(5) . ?
C2 H2 0.9500 . ?
C2 C3 1.377(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.374(3) . ?
C4 C5 1.381(3) . ?
C4 C7 1.505(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.406(5) . ?
C6 H6 0.9500 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?
C7 C8 1.533(3) . ?
C8 H8 1.0000 . ?
C8 C15 1.520(3) . ?
C9 C10 1.381(3) . ?
C9 C14 1.365(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.371(3) . ?
C11 H11 0.9500 . ?
C11 C12 1.374(3) . ?
C12 C13 1.358(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.386(3) . ?
C14 H14 0.9500 . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C15 C16 1.475(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
N2 N1 C8 113.07(17) . . ?
N1 N2 C9 114.32(17) . . ?
O1 N3 O2 123.1(2) . . ?
O1 N3 C12 118.5(2) . . ?
O2 N3 C12 118.35(19) . . ?
C2 C1 H1 120.0 . . ?
C2 C1 C6 120.0(3) . . ?
C6 C1 H1 120.0 . . ?
C1 C2 H2 119.9 . . ?
C1 C2 C3 120.2(3) . . ?
C3 C2 H2 119.9 . . ?
C2 C3 H3 119.1 . . ?
C4 C3 C2 121.7(2) . . ?
C4 C3 H3 119.1 . . ?
C3 C4 C5 118.2(2) . . ?
C3 C4 C7 120.8(2) . . ?
C5 C4 C7 121.0(2) . . ?
C4 C5 H5 120.3 . . ?
C4 C5 C6 119.3(3) . . ?
C6 C5 H5 120.3 . . ?
C1 C6 C5 120.5(3) . . ?
C1 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
C4 C7 H7A 108.9 . . ?
C4 C7 H7B 108.9 . . ?
C4 C7 C8 113.19(19) . . ?
H7A C7 H7B 107.8 . . ?
C8 C7 H7A 108.9 . . ?
C8 C7 H7B 108.9 . . ?
N1 C8 C7 107.30(18) . . ?
N1 C8 H8 109.8 . . ?
N1 C8 C15 108.99(17) . . ?
C7 C8 H8 109.8 . . ?
C15 C8 C7 111.24(17) . . ?
C15 C8 H8 109.8 . . ?
C10 C9 N2 123.30(18) . . ?
C14 C9 N2 116.64(19) . . ?
C14 C9 C10 120.0(2) . . ?
C9 C10 H10 119.9 . . ?
C11 C10 C9 120.28(19) . . ?
C11 C10 H10 119.9 . . ?
C10 C11 H11 120.7 . . ?
C10 C11 C12 118.6(2) . . ?
C12 C11 H11 120.7 . . ?
C11 C12 N3 118.96(19) . . ?
C13 C12 N3 118.85(19) . . ?
C13 C12 C11 122.1(2) . . ?
C12 C13 H13 120.7 . . ?
C12 C13 C14 118.7(2) . . ?
C14 C13 H13 120.7 . . ?
C9 C14 C13 120.3(2) . . ?
C9 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C8 C15 H15A 108.5 . . ?
C8 C15 H15B 108.5 . . ?
H15A C15 H15B 107.5 . . ?
C16 C15 C8 115.23(19) . . ?
C16 C15 H15A 108.5 . . ?
C16 C15 H15B 108.5 . . ?
F1 C16 F2 105.5(2) . . ?
F1 C16 C15 113.9(2) . . ?
F2 C16 C15 112.6(2) . . ?
F3 C16 F1 105.4(3) . . ?
F3 C16 F2 105.8(3) . . ?
F3 C16 C15 113.0(2) . . ?

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 N3 C12 C11 172.4(2) . . . . ?
O1 N3 C12 C13 -4.6(3) . . . . ?
O2 N3 C12 C11 -8.0(3) . . . . ?
O2 N3 C12 C13 175.0(2) . . . . ?
N1 N2 C9 C10 5.7(3) . . . . ?
N1 N2 C9 C14 -177.9(2) . . . . ?
N1 C8 C15 C16 -66.9(3) . . . . ?
N2 N1 C8 C7 -105.3(2) . . . . ?
N2 N1 C8 C15 134.1(2) . . . . ?
N2 C9 C10 C11 176.2(2) . . . . ?
N2 C9 C14 C13 -175.7(2) . . . . ?
N3 C12 C13 C14 176.8(2) . . . . ?
C1 C2 C3 C4 1.2(4) . . . . ?
C2 C1 C6 C5 0.8(5) . . . . ?
C2 C3 C4 C5 -0.5(4) . . . . ?
C2 C3 C4 C7 -179.6(2) . . . . ?
C3 C4 C5 C6 0.0(4) . . . . ?
C3 C4 C7 C8 105.7(2) . . . . ?
C4 C5 C6 C1 -0.1(5) . . . . ?
C4 C7 C8 N1 178.65(17) . . . . ?
C4 C7 C8 C15 -62.2(2) . . . . ?
C5 C4 C7 C8 -73.3(3) . . . . ?
C6 C1 C2 C3 -1.4(5) . . . . ?
C7 C4 C5 C6 179.0(2) . . . . ?
C7 C8 C15 C16 175.0(2) . . . . ?
C8 N1 N2 C9 -179.38(17) . . . . ?
C8 C15 C16 F1 68.5(3) . . . . ?
C8 C15 C16 F2 -171.4(2) . . . . ?
C8 C15 C16 F3 -51.6(3) . . . . ?
C9 C10 C11 C12 -0.6(4) . . . . ?
C10 C9 C14 C13 0.8(4) . . . . ?
C10 C11 C12 N3 -176.2(2) . . . . ?
C10 C11 C12 C13 0.7(4) . . . . ?
C11 C12 C13 C14 -0.1(4) . . . . ?
C12 C13 C14 C9 -0.7(4) . . . . ?
C14 C9 C10 C11 -0.1(4) . . . . ?

_shelx_SHELXL_version_number     2014/7
_olex2_submission_special_instructions 'No special instructions were received'
