# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_exp_5136
_audit_block_doi                 10.5517/cc1j703w
_database_code_depnum_ccdc_archive 'CCDC 1406907'
_audit_update_record             
;
2015-06-16 deposited with the CCDC.
2015-07-14 downloaded from the CCDC.
;
_audit_creation_date             2015-05-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_shelxl_version_number           2014-3
_chemical_name_common            ?
_chemical_name_systematic        
(Z)-2-nitro-1-(1-phenylprop-1-enyl)-4-(trifluoromethyl)benzene
_chemical_formula_moiety         'C16 H12 F3 N O2'
_chemical_formula_sum            'C16 H12 F3 N O2'
_chemical_formula_weight         307.27
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C16 H12 O2 N1 F3'
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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.1909(8)
_cell_length_b                   9.5693(9)
_cell_length_c                   10.5301(8)
_cell_angle_alpha                75.880(7)
_cell_angle_beta                 72.823(8)
_cell_angle_gamma                67.507(9)
_cell_volume                     720.49(12)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1803
_cell_measurement_temperature    180.01(10)
_cell_measurement_theta_max      26.2040
_cell_measurement_theta_min      2.9720
_shelx_estimated_absorpt_T_max   0.988
_shelx_estimated_absorpt_T_min   0.982
_exptl_absorpt_coefficient_mu    0.120
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.33305
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'Yellow '
_exptl_crystal_density_diffrn    1.416
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             316
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0385
_diffrn_reflns_av_unetI/netI     0.0524
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            5726
_diffrn_reflns_point_group_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.014
_diffrn_reflns_theta_min         2.864
_diffrn_ambient_temperature      180.01(10)
_diffrn_detector_area_resol_mean 10.3914
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -81.00   17.00   1.0000    1.3300
omega____ theta____ kappa____ phi______ frames
    -      -11.7954  -57.0000  -30.0000 98

#__ type_ start__ end____ width___ exp.time_
  2 omega -100.00  -75.00   1.0000    1.3300
omega____ theta____ kappa____ phi______ frames
    -      -11.7954  178.0000 -150.0000 25

#__ type_ start__ end____ width___ exp.time_
  3 omega  -87.00  -60.00   1.0000    1.3300
omega____ theta____ kappa____ phi______ frames
    -      -11.7954 -178.0000  -90.0000 27

#__ type_ start__ end____ width___ exp.time_
  4 omega  -41.00   43.00   1.0000    1.3300
omega____ theta____ kappa____ phi______ frames
    -      -11.7954   57.0000  -90.0000 84

#__ type_ start__ end____ width___ exp.time_
  5 omega  -91.00   22.00   1.0000    1.3300
omega____ theta____ kappa____ phi______ frames
    -      -11.7954  -77.0000  120.0000 113
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0412616000
_diffrn_orient_matrix_UB_12      -0.0572817000
_diffrn_orient_matrix_UB_13      0.0188816000
_diffrn_orient_matrix_UB_21      -0.0829139000
_diffrn_orient_matrix_UB_22      0.0559038000
_diffrn_orient_matrix_UB_23      -0.0120027000
_diffrn_orient_matrix_UB_31      0.0260340000
_diffrn_orient_matrix_UB_32      -0.0132129000
_diffrn_orient_matrix_UB_33      -0.0676918000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1803
_reflns_number_total             2770
_reflns_odcompleteness_completeness 99.79
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.97
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.674
_refine_diff_density_min         -0.481
_refine_diff_density_rms         0.067
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         2770
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1275
_refine_ls_R_factor_gt           0.0893
_refine_ls_restrained_S_all      1.063
_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)+(0.1068P)²+0.9932P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2252
_refine_ls_wR_factor_ref         0.2594
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C9(H9), C12(H12), C13(H13), C14(H14), C15(H15),
 C16(H16)
2.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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
C1 C 0.0620(4) 0.6689(4) 0.3435(3) 0.0333(8) Uani 1 1 d . . . . .
C2 C 0.2167(5) 0.6183(4) 0.2447(3) 0.0328(8) Uani 1 1 d . . . . .
C3 C 0.3745(5) 0.6297(4) 0.2604(4) 0.0415(9) Uani 1 1 d . . . . .
H3 H 0.4835 0.5987 0.1941 0.050 Uiso 1 1 calc R . . . .
C4 C 0.3767(5) 0.6845(4) 0.3693(4) 0.0428(9) Uani 1 1 d . . . . .
H4 H 0.4868 0.6889 0.3780 0.051 Uiso 1 1 calc R . . . .
C5 C 0.2193(5) 0.7330(4) 0.4656(3) 0.0355(8) Uani 1 1 d . . . . .
C6 C 0.0600(5) 0.7252(4) 0.4530(4) 0.0381(9) Uani 1 1 d . . . . .
H6 H -0.0492 0.7580 0.5186 0.046 Uiso 1 1 calc R . . . .
C7 C 0.2220(6) 0.7920(5) 0.5834(4) 0.0470(10) Uani 1 1 d . . . . .
C8 C 0.2275(5) 0.5580(4) 0.1226(3) 0.0331(8) Uani 1 1 d . . . . .
C9 C 0.2237(5) 0.6523(4) 0.0055(4) 0.0434(9) Uani 1 1 d . . . . .
H9 H 0.2394 0.6085 -0.0710 0.052 Uiso 1 1 calc R . . . .
C10 C 0.1975(7) 0.8182(4) -0.0174(4) 0.0538(11) Uani 1 1 d . . . . .
H10A H 0.1521 0.8565 0.0691 0.081 Uiso 1 1 calc GR . . . .
H10B H 0.1095 0.8736 -0.0739 0.081 Uiso 1 1 calc GR . . . .
H10C H 0.3135 0.8341 -0.0626 0.081 Uiso 1 1 calc GR . . . .
C11 C 0.2597(5) 0.3924(4) 0.1364(4) 0.0352(8) Uani 1 1 d . . . . .
C12 C 0.2249(5) 0.3328(5) 0.0417(4) 0.0447(9) Uani 1 1 d . . . . .
H12 H 0.1736 0.4000 -0.0299 0.054 Uiso 1 1 calc R . . . .
C13 C 0.2647(6) 0.1777(5) 0.0519(5) 0.0552(11) Uani 1 1 d . . . . .
H13 H 0.2415 0.1393 -0.0136 0.066 Uiso 1 1 calc R . . . .
C14 C 0.3376(7) 0.0770(5) 0.1554(5) 0.0596(12) Uani 1 1 d . . . . .
H14 H 0.3662 -0.0300 0.1605 0.072 Uiso 1 1 calc R . . . .
C15 C 0.3683(6) 0.1340(5) 0.2514(4) 0.0540(11) Uani 1 1 d . . . . .
H15 H 0.4164 0.0660 0.3240 0.065 Uiso 1 1 calc R . . . .
C16 C 0.3292(5) 0.2903(4) 0.2423(4) 0.0442(9) Uani 1 1 d . . . . .
H16 H 0.3501 0.3281 0.3093 0.053 Uiso 1 1 calc R . . . .
F1 F 0.0671(5) 0.8709(6) 0.6443(5) 0.155(2) Uani 1 1 d . . . . .
F2 F 0.3203(7) 0.8790(5) 0.5521(3) 0.1259(17) Uani 1 1 d . . . . .
F3 F 0.2928(8) 0.6838(4) 0.6717(4) 0.140(2) Uani 1 1 d . . . . .
N1 N -0.1127(4) 0.6650(4) 0.3353(3) 0.0459(9) Uani 1 1 d . . . . .
O1 O -0.1202(5) 0.5882(6) 0.2689(4) 0.0963(15) Uani 1 1 d . . . . .
O2 O -0.2440(6) 0.7346(10) 0.4024(7) 0.208(4) Uani 1 1 d . . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0261(18) 0.0404(19) 0.0369(18) -0.0097(14) -0.0073(14) -0.0122(15)
C2 0.0302(19) 0.0339(17) 0.0358(19) -0.0083(14) -0.0076(14) -0.0103(15)
C3 0.029(2) 0.052(2) 0.045(2) -0.0164(17) -0.0011(16) -0.0152(17)
C4 0.032(2) 0.052(2) 0.053(2) -0.0118(18) -0.0130(17) -0.0171(17)
C5 0.035(2) 0.0359(18) 0.039(2) -0.0072(15) -0.0130(16) -0.0109(15)
C6 0.0297(19) 0.047(2) 0.039(2) -0.0145(16) -0.0043(15) -0.0114(16)
C7 0.049(3) 0.056(2) 0.044(2) -0.0090(19) -0.0175(19) -0.021(2)
C8 0.0287(18) 0.0358(18) 0.0349(19) -0.0114(14) -0.0040(14) -0.0097(15)
C9 0.051(2) 0.041(2) 0.034(2) -0.0090(15) -0.0036(17) -0.0140(18)
C10 0.071(3) 0.038(2) 0.044(2) -0.0035(17) -0.005(2) -0.018(2)
C11 0.0300(19) 0.0365(18) 0.040(2) -0.0108(15) -0.0007(15) -0.0147(15)
C12 0.047(2) 0.047(2) 0.044(2) -0.0138(17) -0.0090(18) -0.0168(18)
C13 0.060(3) 0.051(2) 0.063(3) -0.020(2) -0.007(2) -0.025(2)
C14 0.065(3) 0.039(2) 0.078(3) -0.013(2) -0.006(2) -0.025(2)
C15 0.057(3) 0.046(2) 0.056(3) 0.0017(19) -0.010(2) -0.022(2)
C16 0.046(2) 0.047(2) 0.041(2) -0.0055(17) -0.0068(17) -0.0211(19)
F1 0.067(2) 0.275(6) 0.156(4) -0.173(4) -0.023(2) -0.009(3)
F2 0.202(4) 0.180(4) 0.071(2) -0.038(2) -0.010(2) -0.149(4)
F3 0.279(6) 0.083(2) 0.083(2) -0.0010(18) -0.114(3) -0.041(3)
N1 0.0253(17) 0.067(2) 0.051(2) -0.0279(17) -0.0031(15) -0.0134(16)
O1 0.057(2) 0.175(4) 0.094(3) -0.081(3) 0.0020(19) -0.056(3)
O2 0.041(2) 0.414(11) 0.244(7) -0.262(8) 0.021(3) -0.068(4)

_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
C1 C2 1.386(5) . ?
C1 C6 1.380(5) . ?
C1 N1 1.473(4) . ?
C2 C3 1.397(5) . ?
C2 C8 1.499(4) . ?
C3 H3 0.9500 . ?
C3 C4 1.380(5) . ?
C4 H4 0.9500 . ?
C4 C5 1.381(5) . ?
C5 C6 1.381(5) . ?
C5 C7 1.491(5) . ?
C6 H6 0.9500 . ?
C7 F1 1.270(5) . ?
C7 F2 1.294(5) . ?
C7 F3 1.289(5) . ?
C8 C9 1.340(5) . ?
C8 C11 1.481(5) . ?
C9 H9 0.9500 . ?
C9 C10 1.486(5) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.403(5) . ?
C11 C16 1.393(5) . ?
C12 H12 0.9500 . ?
C12 C13 1.376(5) . ?
C13 H13 0.9500 . ?
C13 C14 1.380(7) . ?
C14 H14 0.9500 . ?
C14 C15 1.381(6) . ?
C15 H15 0.9500 . ?
C15 C16 1.389(5) . ?
C16 H16 0.9500 . ?
N1 O1 1.159(4) . ?
N1 O2 1.155(5) . ?

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
C2 C1 N1 120.3(3) . . ?
C6 C1 C2 123.4(3) . . ?
C6 C1 N1 116.3(3) . . ?
C1 C2 C3 115.8(3) . . ?
C1 C2 C8 126.1(3) . . ?
C3 C2 C8 118.1(3) . . ?
C2 C3 H3 119.0 . . ?
C4 C3 C2 122.0(3) . . ?
C4 C3 H3 119.0 . . ?
C3 C4 H4 119.9 . . ?
C3 C4 C5 120.1(3) . . ?
C5 C4 H4 119.9 . . ?
C4 C5 C6 119.7(3) . . ?
C4 C5 C7 120.0(3) . . ?
C6 C5 C7 120.3(3) . . ?
C1 C6 C5 119.0(3) . . ?
C1 C6 H6 120.5 . . ?
C5 C6 H6 120.5 . . ?
F1 C7 C5 114.4(3) . . ?
F1 C7 F2 105.2(4) . . ?
F1 C7 F3 107.1(4) . . ?
F2 C7 C5 113.2(3) . . ?
F3 C7 C5 112.4(3) . . ?
F3 C7 F2 103.8(4) . . ?
C9 C8 C2 118.9(3) . . ?
C9 C8 C11 123.5(3) . . ?
C11 C8 C2 117.4(3) . . ?
C8 C9 H9 116.6 . . ?
C8 C9 C10 126.8(3) . . ?
C10 C9 H9 116.6 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C12 C11 C8 121.1(3) . . ?
C16 C11 C8 121.0(3) . . ?
C16 C11 C12 117.8(3) . . ?
C11 C12 H12 119.8 . . ?
C13 C12 C11 120.4(4) . . ?
C13 C12 H12 119.8 . . ?
C12 C13 H13 119.3 . . ?
C12 C13 C14 121.3(4) . . ?
C14 C13 H13 119.3 . . ?
C13 C14 H14 120.5 . . ?
C13 C14 C15 119.0(4) . . ?
C15 C14 H14 120.5 . . ?
C14 C15 H15 119.8 . . ?
C14 C15 C16 120.3(4) . . ?
C16 C15 H15 119.8 . . ?
C11 C16 H16 119.5 . . ?
C15 C16 C11 121.1(4) . . ?
C15 C16 H16 119.5 . . ?
O1 N1 C1 121.8(3) . . ?
O2 N1 C1 118.5(3) . . ?
O2 N1 O1 119.6(4) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_exp_5108
_audit_block_doi                 10.5517/cc1j704x
_database_code_depnum_ccdc_archive 'CCDC 1406908'
_audit_update_record             
;
2015-06-16 deposited with the CCDC.
2015-07-14 downloaded from the CCDC.
;
_audit_creation_date             2015-05-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_shelxl_version_number           2014-3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C15 H10 F3 N O2'
_chemical_formula_sum            'C15 H10 F3 N O2'
_chemical_formula_weight         293.24
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C15 H4910 N1 O2 F3'
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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   5.8037(6)
_cell_length_b                   15.0490(14)
_cell_length_c                   15.033(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1313.0(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1478
_cell_measurement_temperature    180.01(10)
_cell_measurement_theta_max      23.8550
_cell_measurement_theta_min      3.7350
_shelx_estimated_absorpt_T_max   0.987
_shelx_estimated_absorpt_T_min   0.981
_exptl_absorpt_coefficient_mu    0.127
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.70205
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.483
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             600
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.1
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0326
_diffrn_reflns_av_unetI/netI     0.0438
_diffrn_reflns_Laue_measured_fraction_full 0.930
_diffrn_reflns_Laue_measured_fraction_max 0.953
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            3792
_diffrn_reflns_point_group_measured_fraction_full 0.796
_diffrn_reflns_point_group_measured_fraction_max 0.816
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         25.026
_diffrn_reflns_theta_min         3.027
_diffrn_ambient_temperature      180.01(10)
_diffrn_detector_area_resol_mean 10.3914
_diffrn_measured_fraction_theta_full 0.930
_diffrn_measured_fraction_theta_max 0.953
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -61.00   19.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       10.7017  -38.0000 -180.0000 80

#__ type_ start__ end____ width___ exp.time_
  2 omega   -5.00   21.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.7954  -99.0000   60.0000 26

#__ type_ start__ end____ width___ exp.time_
  3 omega  -89.00  -63.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -11.7954  178.0000 -180.0000 26
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0081124000
_diffrn_orient_matrix_UB_12      0.0389456000
_diffrn_orient_matrix_UB_13      -0.0263712000
_diffrn_orient_matrix_UB_21      -0.0446600000
_diffrn_orient_matrix_UB_22      0.0255753000
_diffrn_orient_matrix_UB_23      0.0356861000
_diffrn_orient_matrix_UB_31      0.1134877000
_diffrn_orient_matrix_UB_32      0.0072929000
_diffrn_orient_matrix_UB_33      0.0159440000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.449
_reflns_Friedel_fraction_full    0.602
_reflns_Friedel_fraction_max     0.618
_reflns_number_gt                1605
_reflns_number_total             1889
_reflns_odcompleteness_completeness 94.74
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     25.97
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.211
_refine_diff_density_min         -0.204
_refine_diff_density_rms         0.049
_refine_ls_abs_structure_details 
;
 Flack x determined using 467 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(7)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.066
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         1889
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0540
_refine_ls_R_factor_gt           0.0426
_refine_ls_restrained_S_all      1.066
_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)+(0.0516P)²+0.0594P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0953
_refine_ls_wR_factor_ref         0.1036
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C6(H6), C11(H11), C12(H12), C13(H13), C14(H14), C15(H15)
2.b X=CH2 refined with riding coordinates:
 C9(H9A,H9B)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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
C1 C 0.4610(6) 0.3569(2) 0.7659(2) 0.0305(8) Uani 1 1 d . . . . .
C2 C 0.4896(6) 0.4415(2) 0.7276(2) 0.0317(8) Uani 1 1 d . . . . .
C3 C 0.6689(6) 0.4925(2) 0.7639(3) 0.0377(9) Uani 1 1 d . . . . .
H3 H 0.6978 0.5498 0.7400 0.045 Uiso 1 1 calc R . . . .
C4 C 0.8041(7) 0.4628(2) 0.8326(3) 0.0412(10) Uani 1 1 d . . . . .
H4 H 0.9227 0.4998 0.8555 0.049 Uiso 1 1 calc R . . . .
C5 C 0.7687(6) 0.3786(2) 0.8691(3) 0.0361(9) Uani 1 1 d . . . . .
C6 C 0.5950(6) 0.3252(2) 0.8340(2) 0.0337(9) Uani 1 1 d . . . . .
H6 H 0.5695 0.2672 0.8570 0.040 Uiso 1 1 calc R . . . .
C7 C 0.9082(6) 0.3463(3) 0.9454(3) 0.0470(10) Uani 1 1 d . . . . .
C8 C 0.3501(6) 0.4779(2) 0.6533(2) 0.0332(8) Uani 1 1 d . . . . .
C9 C 0.2473(7) 0.5566(2) 0.6632(3) 0.0458(10) Uani 1 1 d . . . . .
H9A H 0.2638 0.5885 0.7173 0.055 Uiso 1 1 calc R . . . .
H9B H 0.1576 0.5806 0.6162 0.055 Uiso 1 1 calc R . . . .
C10 C 0.3410(6) 0.42705(19) 0.5682(2) 0.0306(8) Uani 1 1 d . . . . .
C11 C 0.5240(6) 0.3722(2) 0.5433(3) 0.0333(8) Uani 1 1 d . . . . .
H11 H 0.6532 0.3664 0.5816 0.040 Uiso 1 1 calc R . . . .
C12 C 0.5202(6) 0.3258(2) 0.4630(2) 0.0346(8) Uani 1 1 d . . . . .
H12 H 0.6464 0.2890 0.4466 0.041 Uiso 1 1 calc R . . . .
C13 C 0.3321(6) 0.3336(2) 0.4075(3) 0.0375(9) Uani 1 1 d . . . . .
H13 H 0.3288 0.3026 0.3525 0.045 Uiso 1 1 calc R . . . .
C14 C 0.1476(6) 0.3870(2) 0.4321(3) 0.0392(9) Uani 1 1 d . . . . .
H14 H 0.0177 0.3921 0.3940 0.047 Uiso 1 1 calc R . . . .
C15 C 0.1519(6) 0.4328(2) 0.5118(3) 0.0371(9) Uani 1 1 d . . . . .
H15 H 0.0241 0.4687 0.5281 0.045 Uiso 1 1 calc R . . . .
F1 F 0.9165(5) 0.25843(15) 0.9503(2) 0.0794(9) Uani 1 1 d . . . . .
F2 F 0.8273(4) 0.3740(2) 1.02350(18) 0.0731(8) Uani 1 1 d . . . . .
F3 F 1.1255(4) 0.37615(17) 0.94132(19) 0.0664(7) Uani 1 1 d . . . . .
N1 N 0.2743(5) 0.29778(19) 0.7351(2) 0.0359(8) Uani 1 1 d . . . . .
O1 O 0.0962(4) 0.33122(16) 0.70833(19) 0.0427(7) Uani 1 1 d . . . . .
O2 O 0.3077(6) 0.21759(16) 0.7395(2) 0.0660(10) Uani 1 1 d . . . . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
C1 0.0353(19) 0.0264(15) 0.030(2) -0.0045(15) 0.0053(16) -0.0030(15)
C2 0.0383(19) 0.0257(16) 0.031(2) -0.0047(14) 0.0109(16) 0.0004(16)
C3 0.042(2) 0.0244(16) 0.047(2) -0.0049(16) 0.010(2) -0.0069(16)
C4 0.040(2) 0.0332(19) 0.050(3) -0.0101(18) 0.003(2) -0.0081(17)
C5 0.0327(18) 0.039(2) 0.037(2) -0.0082(17) 0.0042(15) 0.0006(17)
C6 0.041(2) 0.0289(17) 0.031(2) -0.0028(15) 0.0046(18) -0.0031(17)
C7 0.040(2) 0.049(2) 0.052(3) -0.011(2) -0.004(2) -0.0034(19)
C8 0.0386(19) 0.0275(17) 0.034(2) 0.0030(15) 0.0107(17) 0.0023(16)
C9 0.062(3) 0.0347(19) 0.041(3) 0.0013(18) 0.003(2) 0.0091(19)
C10 0.0361(18) 0.0246(16) 0.031(2) 0.0070(15) 0.0076(17) 0.0003(15)
C11 0.0346(17) 0.0316(17) 0.034(2) 0.0022(16) 0.0007(16) 0.0009(16)
C12 0.0399(19) 0.0349(18) 0.029(2) 0.0025(16) 0.0088(17) 0.0049(16)
C13 0.049(2) 0.0320(18) 0.031(2) 0.0040(16) 0.0023(18) -0.0015(17)
C14 0.0392(19) 0.043(2) 0.036(2) 0.0083(17) -0.0043(18) 0.0030(18)
C15 0.0374(19) 0.0330(19) 0.041(2) 0.0050(17) 0.0054(19) 0.0071(17)
F1 0.0973(19) 0.0498(14) 0.091(2) 0.0053(14) -0.0495(18) 0.0023(15)
F2 0.0687(15) 0.112(2) 0.0383(16) -0.0044(15) -0.0053(13) -0.0045(18)
F3 0.0416(12) 0.0897(18) 0.0679(19) 0.0060(15) -0.0102(13) -0.0096(13)
N1 0.046(2) 0.0313(17) 0.0302(19) 0.0016(13) -0.0037(15) -0.0115(15)
O1 0.0365(14) 0.0446(14) 0.0471(17) -0.0024(13) -0.0010(13) -0.0053(13)
O2 0.090(2) 0.0262(14) 0.082(3) 0.0036(14) -0.039(2) -0.0130(14)

_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
C1 C2 1.406(5) . ?
C1 C6 1.371(5) . ?
C1 N1 1.477(4) . ?
C2 C3 1.404(5) . ?
C2 C8 1.484(5) . ?
C3 H3 0.9500 . ?
C3 C4 1.372(6) . ?
C4 H4 0.9500 . ?
C4 C5 1.397(5) . ?
C5 C6 1.393(5) . ?
C5 C7 1.486(6) . ?
C6 H6 0.9500 . ?
C7 F1 1.325(4) . ?
C7 F2 1.331(5) . ?
C7 F3 1.340(4) . ?
C8 C9 1.335(5) . ?
C8 C10 1.491(5) . ?
C9 H9A 0.9500 . ?
C9 H9B 0.9500 . ?
C10 C11 1.396(5) . ?
C10 C15 1.390(5) . ?
C11 H11 0.9500 . ?
C11 C12 1.394(5) . ?
C12 H12 0.9500 . ?
C12 C13 1.379(5) . ?
C13 H13 0.9500 . ?
C13 C14 1.390(5) . ?
C14 H14 0.9500 . ?
C14 C15 1.381(5) . ?
C15 H15 0.9500 . ?
N1 O1 1.218(4) . ?
N1 O2 1.224(4) . ?

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
C2 C1 N1 120.2(3) . . ?
C6 C1 C2 123.6(3) . . ?
C6 C1 N1 116.1(3) . . ?
C1 C2 C8 125.3(3) . . ?
C3 C2 C1 115.0(3) . . ?
C3 C2 C8 119.7(3) . . ?
C2 C3 H3 118.7 . . ?
C4 C3 C2 122.6(3) . . ?
C4 C3 H3 118.7 . . ?
C3 C4 H4 119.8 . . ?
C3 C4 C5 120.4(4) . . ?
C5 C4 H4 119.8 . . ?
C4 C5 C7 121.3(4) . . ?
C6 C5 C4 118.8(4) . . ?
C6 C5 C7 119.9(3) . . ?
C1 C6 C5 119.5(3) . . ?
C1 C6 H6 120.2 . . ?
C5 C6 H6 120.2 . . ?
F1 C7 C5 112.9(3) . . ?
F1 C7 F2 106.1(4) . . ?
F1 C7 F3 107.6(3) . . ?
F2 C7 C5 112.7(3) . . ?
F2 C7 F3 105.5(3) . . ?
F3 C7 C5 111.6(3) . . ?
C2 C8 C10 118.4(3) . . ?
C9 C8 C2 119.1(3) . . ?
C9 C8 C10 122.3(4) . . ?
C8 C9 H9A 120.0 . . ?
C8 C9 H9B 120.0 . . ?
H9A C9 H9B 120.0 . . ?
C11 C10 C8 120.4(3) . . ?
C15 C10 C8 121.3(3) . . ?
C15 C10 C11 118.3(3) . . ?
C10 C11 H11 119.5 . . ?
C12 C11 C10 121.1(3) . . ?
C12 C11 H11 119.5 . . ?
C11 C12 H12 120.2 . . ?
C13 C12 C11 119.6(3) . . ?
C13 C12 H12 120.2 . . ?
C12 C13 H13 120.1 . . ?
C12 C13 C14 119.9(4) . . ?
C14 C13 H13 120.1 . . ?
C13 C14 H14 119.8 . . ?
C15 C14 C13 120.4(3) . . ?
C15 C14 H14 119.8 . . ?
C10 C15 H15 119.6 . . ?
C14 C15 C10 120.8(3) . . ?
C14 C15 H15 119.6 . . ?
O1 N1 C1 118.5(3) . . ?
O1 N1 O2 124.1(3) . . ?
O2 N1 C1 117.4(3) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
