# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2017

####################################################################### 
# 
# 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 1532428'
_audit_update_record             
;
2017-02-13 deposited with the CCDC.
2017-06-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H15 F2 N3 O3'
_chemical_formula_weight         323.30

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   P2(1)/n

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   9.1037(4)
_cell_length_b                   18.2464(8)
_cell_length_c                   9.7398(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 105.614(2)
_cell_angle_gamma                90.00
_cell_volume                     1558.17(13)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    7870
_cell_measurement_theta_min      3.11
_cell_measurement_theta_max      24.68

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.378
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             672
_exptl_absorpt_coefficient_mu    0.113
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9755
_exptl_absorpt_correction_T_max  0.9799
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(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  CCD
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23667
_diffrn_reflns_av_R_equivalents  0.0356
_diffrn_reflns_av_sigmaI/netI    0.0277
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.11
_diffrn_reflns_theta_max         27.55
_reflns_number_total             3589
_reflns_number_gt                2213
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_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)+(0.0643P)²+0.2630P] 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         3589
_refine_ls_number_parameters     250
_refine_ls_number_restraints     87
_refine_ls_R_factor_all          0.0879
_refine_ls_R_factor_gt           0.0483
_refine_ls_wR_factor_ref         0.1355
_refine_ls_wR_factor_gt          0.1174
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.024
_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
H12 H 0.313(2) -0.0037(11) 0.050(2) 0.061(6) Uiso 1 1 d . . .
H13 H 0.3941(17) 0.0033(9) 0.3454(16) 0.038(4) Uiso 1 1 d . . .
C1 C 0.5074(2) 0.21681(9) 0.3222(2) 0.0531(4) Uani 1 1 d . . .
C2 C 0.5895(2) 0.27779(11) 0.3055(3) 0.0721(6) Uani 1 1 d . . .
H2 H 0.6211 0.3120 0.3782 0.087 Uiso 1 1 calc R . .
C3 C 0.6230(3) 0.28607(12) 0.1768(3) 0.0866(7) Uani 1 1 d . . .
H3 H 0.6787 0.3267 0.1625 0.104 Uiso 1 1 calc R . .
C4 C 0.5760(3) 0.23574(13) 0.0689(3) 0.0851(7) Uani 1 1 d . . .
H4 H 0.6003 0.2429 -0.0170 0.102 Uiso 1 1 calc R . .
C5 C 0.4927(2) 0.17426(11) 0.0866(2) 0.0646(5) Uani 1 1 d . . .
H5 H 0.4604 0.1402 0.0137 0.078 Uiso 1 1 calc R . .
C6 C 0.45952(19) 0.16532(9) 0.21446(18) 0.0478(4) Uani 1 1 d . . .
C7 C 0.36856(17) 0.10773(9) 0.26643(17) 0.0444(4) Uani 1 1 d . . .
C8 C 0.3775(2) 0.13374(9) 0.4184(2) 0.0518(4) Uani 1 1 d . . .
C9 C 0.4985(3) 0.23556(13) 0.5770(2) 0.0850(7) Uani 1 1 d . . .
H9A H 0.4486 0.2824 0.5657 0.127 Uiso 1 1 calc R . .
H9B H 0.6069 0.2425 0.6077 0.127 Uiso 1 1 calc R . .
H9C H 0.4663 0.2074 0.6469 0.127 Uiso 1 1 calc R . .
N2 N 0.20638(17) 0.11353(10) 0.17726(19) 0.0653(5) Uani 1 1 d . . .
N3 N 0.16415(18) 0.05824(10) 0.10408(19) 0.0679(5) Uani 1 1 d . . .
C12 C 0.2815(2) -0.00005(10) 0.1303(2) 0.0517(4) Uani 1 1 d DU B .
C13 C 0.40607(18) 0.02586(8) 0.25906(18) 0.0415(4) Uani 1 1 d . . .
C15 C 0.2024(3) -0.07026(11) 0.1450(3) 0.0676(6) Uani 1 1 d DU . .
C14 C 0.56660(19) 0.01165(9) 0.25315(18) 0.0467(4) Uani 1 1 d . . .
O2 O 0.66243(13) 0.04474(7) 0.36209(15) 0.0614(4) Uani 1 1 d D A .
C16 C 0.8245(2) 0.03805(14) 0.3760(3) 0.0861(7) Uani 1 1 d U . .
H16A H 0.8702 0.0076 0.4581 0.103 Uiso 0.39(2) 1 calc PR A 1
H16B H 0.8390 0.0136 0.2922 0.103 Uiso 0.39(2) 1 calc PR A 1
H16C H 0.8442 -0.0063 0.3289 0.103 Uiso 0.61(2) 1 d PR A 2
H16D H 0.8801 0.0349 0.4759 0.103 Uiso 0.61(2) 1 d PR A 2
C17A C 0.8995(11) 0.1055(7) 0.392(3) 0.100(4) Uani 0.39(2) 1 d PDU A 1
H17A H 1.0058 0.0979 0.4001 0.150 Uiso 0.39(2) 1 calc PR A 1
H17B H 0.8881 0.1294 0.4763 0.150 Uiso 0.39(2) 1 calc PR A 1
H17C H 0.8560 0.1357 0.3103 0.150 Uiso 0.39(2) 1 calc PR A 1
C17B C 0.8762(8) 0.1011(5) 0.3117(16) 0.098(3) Uani 0.61(2) 1 d PDU A 2
H17D H 0.9833 0.0964 0.3203 0.147 Uiso 0.61(2) 1 calc PR A 2
H17E H 0.8582 0.1448 0.3594 0.147 Uiso 0.61(2) 1 calc PR A 2
H17F H 0.8214 0.1037 0.2128 0.147 Uiso 0.61(2) 1 calc PR A 2
F1A F 0.2932(14) -0.1273(3) 0.136(3) 0.093(3) Uani 0.41(5) 1 d PDU B 1
F2A F 0.181(3) -0.0757(9) 0.2760(15) 0.105(3) Uani 0.41(5) 1 d PDU B 1
F1B F 0.3035(10) -0.1251(3) 0.178(2) 0.103(2) Uani 0.59(5) 1 d PDU B 2
F2B F 0.1391(16) -0.0656(5) 0.2547(11) 0.093(2) Uani 0.59(5) 1 d PDU B 2
N1 N 0.45826(17) 0.19688(8) 0.44150(16) 0.0557(4) Uani 1 1 d . . .
O1 O 0.32210(19) 0.10233(8) 0.50174(16) 0.0771(4) Uani 1 1 d . . .
O3 O 0.60212(15) -0.02381(8) 0.16411(14) 0.0707(4) Uani 1 1 d . . .
H15 H 0.120(3) -0.0839(11) 0.063(2) 0.074(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
C1 C2 1.374(3) . ?
C1 C6 1.388(3) . ?
C1 N1 1.401(2) . ?
C2 C3 1.376(3) . ?
C3 C4 1.374(4) . ?
C4 C5 1.391(3) . ?
C5 C6 1.367(3) . ?
C6 C7 1.507(2) . ?
C7 N2 1.502(2) . ?
C7 C8 1.535(2) . ?
C7 C13 1.538(2) . ?
C8 O1 1.209(2) . ?
C8 N1 1.353(2) . ?
C9 N1 1.454(3) . ?
N2 N3 1.235(2) . ?
N3 C12 1.480(2) . ?
C12 C15 1.495(3) . ?
C12 C13 1.522(2) . ?
C13 C14 1.501(2) . ?
C15 F1B 1.339(5) . ?
C15 F2B 1.346(5) . ?
C15 F2A 1.346(6) . ?
C15 F1A 1.346(6) . ?
C14 O3 1.194(2) . ?
C14 O2 1.324(2) . ?
O2 C16 1.450(2) . ?
C16 C17A 1.396(10) . ?
C16 C17B 1.447(7) . ?

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 C6 121.92(19) . . ?
C2 C1 N1 127.85(18) . . ?
C6 C1 N1 110.23(15) . . ?
C1 C2 C3 117.2(2) . . ?
C2 C3 C4 121.6(2) . . ?
C3 C4 C5 120.8(2) . . ?
C6 C5 C4 118.1(2) . . ?
C5 C6 C1 120.39(16) . . ?
C5 C6 C7 131.67(17) . . ?
C1 C6 C7 107.88(15) . . ?
N2 C7 C6 107.47(13) . . ?
N2 C7 C8 108.94(14) . . ?
C6 C7 C8 102.52(13) . . ?
N2 C7 C13 103.73(13) . . ?
C6 C7 C13 120.82(13) . . ?
C8 C7 C13 112.97(13) . . ?
O1 C8 N1 126.73(17) . . ?
O1 C8 C7 125.26(16) . . ?
N1 C8 C7 108.01(14) . . ?
N3 N2 C7 112.40(15) . . ?
N2 N3 C12 112.90(14) . . ?
N3 C12 C15 106.79(15) . . ?
N3 C12 C13 105.21(14) . . ?
C15 C12 C13 117.30(17) . . ?
C14 C13 C12 115.62(15) . . ?
C14 C13 C7 113.59(13) . . ?
C12 C13 C7 102.38(13) . . ?
F1B C15 F2B 105.7(4) . . ?
F1B C15 F2A 89.1(9) . . ?
F2B C15 F2A 18.0(11) . . ?
F1B C15 F1A 16.9(10) . . ?
F2B C15 F1A 120.0(8) . . ?
F2A C15 F1A 104.6(6) . . ?
F1B C15 C12 110.3(4) . . ?
F2B C15 C12 110.0(4) . . ?
F2A C15 C12 110.5(5) . . ?
F1A C15 C12 109.7(5) . . ?
O3 C14 O2 125.46(16) . . ?
O3 C14 C13 125.33(16) . . ?
O2 C14 C13 109.21(15) . . ?
C14 O2 C16 118.11(17) . . ?
C17A C16 C17B 30.8(5) . . ?
C17A C16 O2 113.0(5) . . ?
C17B C16 O2 109.5(3) . . ?
C8 N1 C1 111.33(15) . . ?
C8 N1 C9 123.88(16) . . ?
C1 N1 C9 124.63(16) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.55
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.203
_refine_diff_density_min         -0.180
_refine_diff_density_rms         0.034
####################################################################### 
# 
# 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_33_2_3
_database_code_depnum_ccdc_archive 'CCDC 1541877'
_audit_update_record             
;
2017-04-03 deposited with the CCDC.
2017-06-13 downloaded from the CCDC.
;
_audit_creation_date             2017-04-03
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H17 F2 N3 O4'
_chemical_formula_sum            'C16 H17 F2 N3 O4'
_chemical_formula_weight         353.32
_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      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                   8.1522(5)
_cell_length_b                   9.1400(6)
_cell_length_c                   12.4646(8)
_cell_angle_alpha                89.726(5)
_cell_angle_beta                 76.757(5)
_cell_angle_gamma                63.771(7)
_cell_volume                     806.00(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3281
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      29.1130
_cell_measurement_theta_min      4.0400
_shelx_estimated_absorpt_T_max   0.979
_shelx_estimated_absorpt_T_min   0.967
_exptl_absorpt_coefficient_mu    0.121
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.61746
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.456
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             368
_exptl_crystal_size_max          0.28
_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  0.0249
_diffrn_reflns_av_unetI/netI     0.0439
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.829
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            7228
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.829
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         29.538
_diffrn_reflns_theta_min         3.379
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.829
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      1.00  88.00   1.00    1.00    --   11.74  77.00 -30.00   87
  2  ω    -64.00  42.00   1.00    1.00    --   11.74 -77.00-120.00  106
  3  ω    -68.00 -27.00   1.00    1.00    --   11.74 -19.00 -60.00   41
  4  ω    -79.00  20.00   1.00    1.00    --  -11.51 -77.00  90.00   99
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0286002000
_diffrn_orient_matrix_UB_12      0.0428848000
_diffrn_orient_matrix_UB_13      -0.0452260000
_diffrn_orient_matrix_UB_21      0.0404622000
_diffrn_orient_matrix_UB_22      0.0517585000
_diffrn_orient_matrix_UB_23      0.0095242000
_diffrn_orient_matrix_UB_31      0.0871563000
_diffrn_orient_matrix_UB_32      -0.0553066000
_diffrn_orient_matrix_UB_33      -0.0363822000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3137
_reflns_number_total             3757
_reflns_odcompleteness_completeness 99.76
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.357
_refine_diff_density_min         -0.383
_refine_diff_density_rms         0.068
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     229
_refine_ls_number_reflns         3757
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0566
_refine_ls_R_factor_gt           0.0467
_refine_ls_restrained_S_all      1.052
_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)+(0.0488P)²+0.2867P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1074
_refine_ls_wR_factor_ref         0.1151
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C9(H9), C10(H10), C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C15(H15a,H15b)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C4(H4), C3(H3)
2.d Idealised Me refined as rotating group:
 C13(H13a,H13b,H13c), C12(H12a,H12b,H12c), C16(H16a,H16b,H16c)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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
F2 F 0.39584(14) 0.75694(14) 1.10445(8) 0.0305(3) Uani 1 1 d . . . . .
F1 F 0.24733(14) 0.66235(14) 1.02277(8) 0.0297(3) Uani 1 1 d . . . . .
O4 O 0.86351(14) 0.59540(14) 0.83082(9) 0.0184(3) Uani 1 1 d . . . . .
O2 O 0.54966(15) 0.47345(14) 0.68545(9) 0.0186(2) Uani 1 1 d . . . . .
O1 O 0.88899(16) 0.72863(14) 0.39618(9) 0.0210(3) Uani 1 1 d . . . . .
O3 O 0.70106(17) 0.84922(16) 0.91964(11) 0.0327(3) Uani 1 1 d . . . . .
N1 N 0.68663(17) 0.60683(16) 0.56733(10) 0.0147(3) Uani 1 1 d . . . . .
N2 N 0.29076(17) 0.83262(16) 0.76458(10) 0.0159(3) Uani 1 1 d . . . . .
N3 N 0.21130(18) 0.88702(16) 0.86344(10) 0.0172(3) Uani 1 1 d . . . . .
C14 C 0.7061(2) 0.7307(2) 0.87550(12) 0.0159(3) Uani 1 1 d . . . . .
C9 C 0.5348(2) 0.71523(19) 0.86087(12) 0.0137(3) Uani 1 1 d . . . . .
H9 H 0.547657 0.606030 0.876512 0.016 Uiso 1 1 calc R . . . .
C8 C 0.5035(2) 0.74686(18) 0.74382(11) 0.0130(3) Uani 1 1 d . . . . .
C1 C 0.5810(2) 0.84951(19) 0.67584(12) 0.0142(3) Uani 1 1 d . . . . .
C6 C 0.6876(2) 0.76143(18) 0.57310(12) 0.0141(3) Uani 1 1 d . . . . .
C13 C 0.7679(2) 0.4844(2) 0.47099(12) 0.0181(3) Uani 1 1 d . . . . .
H13A H 0.705277 0.529502 0.413544 0.027 Uiso 1 1 calc GR . . . .
H13B H 0.751574 0.389368 0.491562 0.027 Uiso 1 1 calc GR . . . .
H13C H 0.900178 0.453648 0.444442 0.027 Uiso 1 1 calc GR . . . .
C5 C 0.7782(2) 0.8260(2) 0.49250(12) 0.0165(3) Uani 1 1 d . . . . .
C7 C 0.5809(2) 0.59019(19) 0.66433(12) 0.0142(3) Uani 1 1 d . . . . .
C15 C 1.0404(2) 0.5951(2) 0.83799(14) 0.0216(4) Uani 1 1 d . . . . .
H15A H 1.021073 0.657561 0.906404 0.026 Uiso 1 1 calc R . . . .
H15B H 1.084509 0.644700 0.776221 0.026 Uiso 1 1 calc R . . . .
C2 C 0.5544(2) 1.0072(2) 0.70112(13) 0.0188(3) Uani 1 1 d . . . . .
H2 H 0.482716 1.065617 0.770140 0.023 Uiso 1 1 calc R . . . .
C10 C 0.3486(2) 0.8468(2) 0.93310(12) 0.0164(3) Uani 1 1 d . . . . .
H10 H 0.364040 0.944514 0.948085 0.020 Uiso 1 1 calc R . . . .
C4 C 0.7492(2) 0.9860(2) 0.51778(14) 0.0206(3) Uani 1 1 d . . . . .
H4 H 0.805400 1.033702 0.465210 0.025 Uiso 1 1 calc R . . . .
C3 C 0.6383(2) 1.0751(2) 0.61986(14) 0.0223(4) Uani 1 1 d . . . . .
H3 H 0.619986 1.181757 0.634002 0.027 Uiso 1 1 calc R . . . .
C11 C 0.2694(2) 0.7995(2) 1.04142(13) 0.0216(4) Uani 1 1 d . . . . .
H11 H 0.148541 0.890393 1.080710 0.026 Uiso 1 1 calc R . . . .
C12 C 0.9990(2) 0.7873(2) 0.31888(14) 0.0238(4) Uani 1 1 d . . . . .
H12A H 1.076211 0.704878 0.257087 0.036 Uiso 1 1 calc GR . . . .
H12B H 1.078248 0.811306 0.354564 0.036 Uiso 1 1 calc GR . . . .
H12C H 0.916240 0.885201 0.293099 0.036 Uiso 1 1 calc GR . . . .
C16 C 1.1830(2) 0.4202(2) 0.83498(14) 0.0250(4) Uani 1 1 d . . . . .
H16A H 1.200817 0.359519 0.767105 0.038 Uiso 1 1 calc GR . . . .
H16B H 1.138576 0.372685 0.896806 0.038 Uiso 1 1 calc GR . . . .
H16C H 1.301007 0.416332 0.839114 0.038 Uiso 1 1 calc GR . . . .


_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
F2 C11 1.3582(17) . ?
F1 C11 1.371(2) . ?
O4 C14 1.3279(19) . ?
O4 C15 1.4644(17) . ?
O2 C7 1.2161(18) . ?
O1 C5 1.3611(18) . ?
O1 C12 1.4297(18) . ?
O3 C14 1.1972(19) . ?
N1 C6 1.4190(19) . ?
N1 C13 1.4583(19) . ?
N1 C7 1.3656(19) . ?
N2 N3 1.2413(18) . ?
N2 C8 1.5110(18) . ?
N3 C10 1.4899(18) . ?
C14 C9 1.5145(19) . ?
C9 H9 0.9800 . ?
C9 C8 1.5425(19) . ?
C9 C10 1.527(2) . ?
C8 C1 1.507(2) . ?
C8 C7 1.536(2) . ?
C1 C6 1.387(2) . ?
C1 C2 1.386(2) . ?
C6 C5 1.394(2) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C5 C4 1.400(2) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C15 C16 1.499(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.390(2) . ?
C10 H10 0.9800 . ?
C10 C11 1.506(2) . ?
C4 H4 0.9300 . ?
C4 C3 1.390(2) . ?
C3 H3 0.9300 . ?
C11 H11 0.9800 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 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
C14 O4 C15 116.13(12) . . ?
C5 O1 C12 117.73(13) . . ?
C6 N1 C13 127.26(12) . . ?
C7 N1 C6 110.48(12) . . ?
C7 N1 C13 122.01(12) . . ?
N3 N2 C8 112.04(11) . . ?
N2 N3 C10 112.25(12) . . ?
O4 C14 C9 110.55(12) . . ?
O3 C14 O4 124.52(14) . . ?
O3 C14 C9 124.92(14) . . ?
C14 C9 H9 109.8 . . ?
C14 C9 C8 112.59(12) . . ?
C14 C9 C10 113.23(12) . . ?
C8 C9 H9 109.8 . . ?
C10 C9 H9 109.8 . . ?
C10 C9 C8 101.26(11) . . ?
N2 C8 C9 103.44(11) . . ?
N2 C8 C7 108.37(10) . . ?
C1 C8 N2 108.13(12) . . ?
C1 C8 C9 119.69(11) . . ?
C1 C8 C7 102.69(11) . . ?
C7 C8 C9 114.13(12) . . ?
C6 C1 C8 108.35(13) . . ?
C2 C1 C8 130.07(14) . . ?
C2 C1 C6 121.54(14) . . ?
C1 C6 N1 110.20(13) . . ?
C1 C6 C5 121.16(14) . . ?
C5 C6 N1 128.64(14) . . ?
N1 C13 H13A 109.5 . . ?
N1 C13 H13B 109.5 . . ?
N1 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O1 C5 C6 117.73(14) . . ?
O1 C5 C4 125.13(14) . . ?
C6 C5 C4 117.14(14) . . ?
O2 C7 N1 126.80(14) . . ?
O2 C7 C8 124.91(13) . . ?
N1 C7 C8 108.28(12) . . ?
O4 C15 H15A 110.2 . . ?
O4 C15 H15B 110.2 . . ?
O4 C15 C16 107.70(13) . . ?
H15A C15 H15B 108.5 . . ?
C16 C15 H15A 110.2 . . ?
C16 C15 H15B 110.2 . . ?
C1 C2 H2 121.1 . . ?
C1 C2 C3 117.74(15) . . ?
C3 C2 H2 121.1 . . ?
N3 C10 C9 104.92(11) . . ?
N3 C10 H10 108.9 . . ?
N3 C10 C11 108.54(12) . . ?
C9 C10 H10 108.9 . . ?
C11 C10 C9 116.49(14) . . ?
C11 C10 H10 108.9 . . ?
C5 C4 H4 119.3 . . ?
C3 C4 C5 121.32(15) . . ?
C3 C4 H4 119.3 . . ?
C2 C3 C4 121.02(15) . . ?
C2 C3 H3 119.5 . . ?
C4 C3 H3 119.5 . . ?
F2 C11 F1 105.98(13) . . ?
F2 C11 C10 109.30(13) . . ?
F2 C11 H11 110.5 . . ?
F1 C11 C10 110.04(12) . . ?
F1 C11 H11 110.5 . . ?
C10 C11 H11 110.5 . . ?
O1 C12 H12A 109.5 . . ?
O1 C12 H12B 109.5 . . ?
O1 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

_olex2_date_sample_data_collection 2017-03-27
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.636
_oxdiff_exptl_absorpt_empirical_full_min 0.687
####################################################################### 
# 
# 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_120_3
_database_code_depnum_ccdc_archive 'CCDC 1541878'
_audit_update_record             
;
2017-04-03 deposited with the CCDC.
2017-06-13 downloaded from the CCDC.
;
_audit_creation_date             2017-03-28
_audit_creation_method           
;
Olex2 1.2
(compiled 2017.03.02 svn.r3394 for OlexSys, GUI svn.r5324)
;
_shelx_SHELXL_version_number     2016/6
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H17 F2 N3 O3'
_chemical_formula_sum            'C20 H17 F2 N3 O3'
_chemical_formula_weight         385.36
_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/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   10.7505(5)
_cell_length_b                   12.0115(5)
_cell_length_c                   14.5754(7)
_cell_angle_alpha                90
_cell_angle_beta                 106.876(5)
_cell_angle_gamma                90
_cell_volume                     1801.05(14)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5573
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      29.2810
_cell_measurement_theta_min      4.3150
_shelx_estimated_absorpt_T_max   0.978
_shelx_estimated_absorpt_T_min   0.967
_exptl_absorpt_coefficient_mu    0.111
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.65111
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.421
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.2
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0448
_diffrn_reflns_av_unetI/netI     0.0446
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.882
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            15974
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.882
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.502
_diffrn_reflns_theta_min         3.257
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.2684
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.882
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -12.00  85.00   1.00    1.74    --   11.74  37.00 -30.00   97
  2  ω    -17.00  29.00   1.00    1.74    --  -11.43 -99.00 120.00   46
  3  ω    -18.00  32.00   1.00    1.74    --   11.74 -57.00   0.00   50
  4  ω     40.00  99.00   1.00    1.74    --   11.74-178.00-180.00   59
  5  ω    -68.00  27.00   1.00    1.74    --   11.74 -19.00 150.00   95
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0365053000
_diffrn_orient_matrix_UB_12      0.0385356000
_diffrn_orient_matrix_UB_13      -0.0185426000
_diffrn_orient_matrix_UB_21      -0.0416750000
_diffrn_orient_matrix_UB_22      0.0436346000
_diffrn_orient_matrix_UB_23      0.0055574000
_diffrn_orient_matrix_UB_31      0.0410445000
_diffrn_orient_matrix_UB_32      0.0100146000
_diffrn_orient_matrix_UB_33      0.0470259000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3680
_reflns_number_total             4427
_reflns_odcompleteness_completeness 99.74
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_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    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.378
_refine_diff_density_min         -0.298
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         4427
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0580
_refine_ls_R_factor_gt           0.0461
_refine_ls_restrained_S_all      1.030
_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)+(0.0450P)²+0.8132P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1027
_refine_ls_wR_factor_ref         0.1117
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C10(H10), C9(H9), C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 C15(H15), C2(H2), C5(H5), C4(H4), C19(H19), C16(H16), C18(H18), C17(H17),
 C3(H3)
2.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_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 0.71718(9) 0.22680(8) 0.64649(6) 0.0247(2) Uani 1 1 d . . . . .
F2 F 0.81138(8) 0.21408(8) 0.53229(7) 0.0281(2) Uani 1 1 d . . . . .
O2 O 0.31296(10) 0.19813(8) 0.59854(7) 0.0155(2) Uani 1 1 d . . . . .
O1 O 0.32756(10) 0.46815(8) 0.45675(7) 0.0180(2) Uani 1 1 d . . . . .
O3 O 0.45027(10) 0.06370(9) 0.58145(8) 0.0202(2) Uani 1 1 d . . . . .
N1 N 0.15530(11) 0.35593(9) 0.37480(8) 0.0133(3) Uani 1 1 d . . . . .
N3 N 0.56373(12) 0.26341(10) 0.39173(8) 0.0157(3) Uani 1 1 d . . . . .
N2 N 0.45060(12) 0.29623(10) 0.35451(9) 0.0161(3) Uani 1 1 d . . . . .
C009 C 0.41107(13) 0.15790(12) 0.56934(9) 0.0126(3) Uani 1 1 d . . . . .
C1 C 0.14103(14) 0.24318(11) 0.34411(10) 0.0131(3) Uani 1 1 d . . . . .
C10 C 0.58271(13) 0.21434(11) 0.48865(10) 0.0129(3) Uani 1 1 d . . . . .
H10 H 0.587954 0.133071 0.485074 0.015 Uiso 1 1 calc R . . . .
C9 C 0.46150(13) 0.24711(11) 0.51659(10) 0.0117(3) Uani 1 1 d . . . . .
H9 H 0.479498 0.314743 0.555838 0.014 Uiso 1 1 calc R . . . .
C14 C 0.04959(13) 0.43111(12) 0.36769(10) 0.0131(3) Uani 1 1 d . . . . .
C8 C 0.28352(13) 0.38032(12) 0.42031(10) 0.0134(3) Uani 1 1 d . . . . .
C6 C 0.26198(13) 0.19059(12) 0.37024(9) 0.0131(3) Uani 1 1 d . . . . .
C15 C 0.05209(14) 0.53613(12) 0.32891(10) 0.0151(3) Uani 1 1 d . . . . .
H15 H 0.121405 0.557554 0.306787 0.018 Uiso 1 1 calc R . . . .
C2 C 0.02948(14) 0.18850(12) 0.29301(10) 0.0166(3) Uani 1 1 d . . . . .
H2 H -0.050744 0.224183 0.275660 0.020 Uiso 1 1 calc R . . . .
C7 C 0.36407(13) 0.27442(11) 0.41847(10) 0.0127(3) Uani 1 1 d . . . . .
C5 C 0.27297(14) 0.08037(12) 0.34696(10) 0.0158(3) Uani 1 1 d . . . . .
H5 H 0.353150 0.044631 0.365144 0.019 Uiso 1 1 calc R . . . .
C4 C 0.16098(15) 0.02369(12) 0.29548(10) 0.0182(3) Uani 1 1 d . . . . .
H4 H 0.166365 -0.050666 0.279264 0.022 Uiso 1 1 calc R . . . .
C19 C -0.05347(14) 0.39748(12) 0.40051(10) 0.0161(3) Uani 1 1 d . . . . .
H19 H -0.053616 0.327158 0.427177 0.019 Uiso 1 1 calc R . . . .
C16 C -0.05020(15) 0.60908(12) 0.32344(11) 0.0182(3) Uani 1 1 d . . . . .
H16 H -0.048840 0.680199 0.298525 0.022 Uiso 1 1 calc R . . . .
C11 C 0.70788(14) 0.25961(12) 0.55502(11) 0.0171(3) Uani 1 1 d . . . . .
H11 H 0.709894 0.340993 0.550909 0.021 Uiso 1 1 calc R . . . .
C18 C -0.15642(14) 0.47027(13) 0.39299(10) 0.0185(3) Uani 1 1 d . . . . .
H18 H -0.226919 0.448105 0.413408 0.022 Uiso 1 1 calc R . . . .
C12 C 0.24565(15) 0.11893(13) 0.64368(11) 0.0193(3) Uani 1 1 d . . . . .
H12A H 0.213633 0.157073 0.690952 0.023 Uiso 1 1 calc R . . . .
H12B H 0.305784 0.061504 0.676252 0.023 Uiso 1 1 calc R . . . .
C17 C -0.15424(15) 0.57591(12) 0.35509(11) 0.0192(3) Uani 1 1 d . . . . .
H17 H -0.222842 0.624693 0.350893 0.023 Uiso 1 1 calc R . . . .
C3 C 0.04171(15) 0.07768(12) 0.26839(11) 0.0188(3) Uani 1 1 d . . . . .
H3 H -0.031608 0.039146 0.233080 0.023 Uiso 1 1 calc R . . . .
C13 C 0.13427(18) 0.06688(18) 0.56943(13) 0.0384(5) Uani 1 1 d . . . . .
H13A H 0.166557 0.026937 0.524043 0.058 Uiso 1 1 calc GR . . . .
H13B H 0.075459 0.123970 0.536782 0.058 Uiso 1 1 calc GR . . . .
H13C H 0.089398 0.016389 0.599863 0.058 Uiso 1 1 calc GR . . . .


_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 C11 1.3658(17) . ?
F2 C11 1.3642(17) . ?
O2 C009 1.3369(17) . ?
O2 C12 1.4622(17) . ?
O1 C8 1.2138(17) . ?
O3 C009 1.2024(17) . ?
N1 C1 1.4205(18) . ?
N1 C14 1.4316(17) . ?
N1 C8 1.3766(18) . ?
N3 N2 1.2433(17) . ?
N3 C10 1.4890(18) . ?
N2 C7 1.5188(18) . ?
C009 C9 1.5084(19) . ?
C1 C6 1.3954(19) . ?
C1 C2 1.380(2) . ?
C10 H10 0.9800 . ?
C10 C9 1.5254(19) . ?
C10 C11 1.512(2) . ?
C9 H9 0.9800 . ?
C9 C7 1.5429(19) . ?
C14 C15 1.386(2) . ?
C14 C19 1.388(2) . ?
C8 C7 1.5433(19) . ?
C6 C7 1.5049(19) . ?
C6 C5 1.380(2) . ?
C15 H15 0.9300 . ?
C15 C16 1.390(2) . ?
C2 H2 0.9300 . ?
C2 C3 1.395(2) . ?
C5 H5 0.9300 . ?
C5 C4 1.397(2) . ?
C4 H4 0.9300 . ?
C4 C3 1.388(2) . ?
C19 H19 0.9300 . ?
C19 C18 1.390(2) . ?
C16 H16 0.9300 . ?
C16 C17 1.386(2) . ?
C11 H11 0.9800 . ?
C18 H18 0.9300 . ?
C18 C17 1.387(2) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C13 1.498(2) . ?
C17 H17 0.9300 . ?
C3 H3 0.9300 . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 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
C009 O2 C12 116.56(11) . . ?
C1 N1 C14 124.60(11) . . ?
C8 N1 C1 110.86(11) . . ?
C8 N1 C14 124.29(12) . . ?
N2 N3 C10 112.75(12) . . ?
N3 N2 C7 111.92(11) . . ?
O2 C009 C9 109.81(11) . . ?
O3 C009 O2 124.66(13) . . ?
O3 C009 C9 125.50(13) . . ?
C6 C1 N1 109.80(12) . . ?
C2 C1 N1 128.39(13) . . ?
C2 C1 C6 121.77(13) . . ?
N3 C10 H10 109.8 . . ?
N3 C10 C9 104.99(11) . . ?
N3 C10 C11 108.42(11) . . ?
C9 C10 H10 109.8 . . ?
C11 C10 H10 109.8 . . ?
C11 C10 C9 114.01(11) . . ?
C009 C9 C10 114.46(11) . . ?
C009 C9 H9 109.3 . . ?
C009 C9 C7 112.07(11) . . ?
C10 C9 H9 109.3 . . ?
C10 C9 C7 102.13(11) . . ?
C7 C9 H9 109.3 . . ?
C15 C14 N1 119.65(12) . . ?
C15 C14 C19 121.16(13) . . ?
C19 C14 N1 119.19(13) . . ?
O1 C8 N1 127.20(13) . . ?
O1 C8 C7 125.06(13) . . ?
N1 C8 C7 107.74(11) . . ?
C1 C6 C7 108.67(12) . . ?
C5 C6 C1 120.43(13) . . ?
C5 C6 C7 130.83(13) . . ?
C14 C15 H15 120.4 . . ?
C14 C15 C16 119.24(14) . . ?
C16 C15 H15 120.4 . . ?
C1 C2 H2 121.3 . . ?
C1 C2 C3 117.44(13) . . ?
C3 C2 H2 121.3 . . ?
N2 C7 C9 103.51(10) . . ?
N2 C7 C8 108.37(11) . . ?
C9 C7 C8 113.11(11) . . ?
C6 C7 N2 108.80(11) . . ?
C6 C7 C9 119.84(11) . . ?
C6 C7 C8 102.87(11) . . ?
C6 C5 H5 120.7 . . ?
C6 C5 C4 118.53(13) . . ?
C4 C5 H5 120.7 . . ?
C5 C4 H4 119.8 . . ?
C3 C4 C5 120.40(14) . . ?
C3 C4 H4 119.8 . . ?
C14 C19 H19 120.4 . . ?
C14 C19 C18 119.13(14) . . ?
C18 C19 H19 120.4 . . ?
C15 C16 H16 120.0 . . ?
C17 C16 C15 120.06(14) . . ?
C17 C16 H16 120.0 . . ?
F1 C11 C10 108.67(12) . . ?
F1 C11 H11 110.5 . . ?
F2 C11 F1 106.72(11) . . ?
F2 C11 C10 109.73(12) . . ?
F2 C11 H11 110.5 . . ?
C10 C11 H11 110.5 . . ?
C19 C18 H18 119.9 . . ?
C17 C18 C19 120.13(14) . . ?
C17 C18 H18 119.9 . . ?
O2 C12 H12A 109.7 . . ?
O2 C12 H12B 109.7 . . ?
O2 C12 C13 110.04(12) . . ?
H12A C12 H12B 108.2 . . ?
C13 C12 H12A 109.7 . . ?
C13 C12 H12B 109.7 . . ?
C16 C17 C18 120.27(14) . . ?
C16 C17 H17 119.9 . . ?
C18 C17 H17 119.9 . . ?
C2 C3 H3 119.3 . . ?
C4 C3 C2 121.40(14) . . ?
C4 C3 H3 119.3 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13B 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?

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
O2 C009 C9 C10 174.10(11) . . . . ?
O2 C009 C9 C7 -70.21(14) . . . . ?
O1 C8 C7 N2 -67.84(17) . . . . ?
O1 C8 C7 C9 46.32(19) . . . . ?
O1 C8 C7 C6 177.05(13) . . . . ?
O3 C009 C9 C10 -7.7(2) . . . . ?
O3 C009 C9 C7 107.96(16) . . . . ?
N1 C1 C6 C7 -2.00(15) . . . . ?
N1 C1 C6 C5 -179.21(12) . . . . ?
N1 C1 C2 C3 177.74(13) . . . . ?
N1 C14 C15 C16 -179.18(13) . . . . ?
N1 C14 C19 C18 -179.58(12) . . . . ?
N1 C8 C7 N2 112.85(12) . . . . ?
N1 C8 C7 C9 -132.98(12) . . . . ?
N1 C8 C7 C6 -2.25(14) . . . . ?
N3 N2 C7 C9 14.31(15) . . . . ?
N3 N2 C7 C8 134.66(12) . . . . ?
N3 N2 C7 C6 -114.18(13) . . . . ?
N3 C10 C9 C009 141.39(11) . . . . ?
N3 C10 C9 C7 20.06(13) . . . . ?
N3 C10 C11 F1 172.04(11) . . . . ?
N3 C10 C11 F2 -71.62(14) . . . . ?
N2 N3 C10 C9 -12.81(15) . . . . ?
N2 N3 C10 C11 -135.03(13) . . . . ?
C009 O2 C12 C13 -90.34(16) . . . . ?
C009 C9 C7 N2 -143.30(11) . . . . ?
C009 C9 C7 C8 99.63(13) . . . . ?
C009 C9 C7 C6 -21.97(17) . . . . ?
C1 N1 C14 C15 -131.24(14) . . . . ?
C1 N1 C14 C19 49.18(19) . . . . ?
C1 N1 C8 O1 -178.10(14) . . . . ?
C1 N1 C8 C7 1.18(15) . . . . ?
C1 C6 C7 N2 -112.24(12) . . . . ?
C1 C6 C7 C9 129.09(13) . . . . ?
C1 C6 C7 C8 2.55(14) . . . . ?
C1 C6 C5 C4 1.1(2) . . . . ?
C1 C2 C3 C4 1.0(2) . . . . ?
C10 N3 N2 C7 -1.11(16) . . . . ?
C10 C9 C7 N2 -20.34(13) . . . . ?
C10 C9 C7 C8 -137.40(12) . . . . ?
C10 C9 C7 C6 101.00(14) . . . . ?
C9 C10 C11 F1 55.49(15) . . . . ?
C9 C10 C11 F2 171.84(11) . . . . ?
C14 N1 C1 C6 -173.94(12) . . . . ?
C14 N1 C1 C2 8.3(2) . . . . ?
C14 N1 C8 O1 -3.6(2) . . . . ?
C14 N1 C8 C7 175.64(12) . . . . ?
C14 C15 C16 C17 -1.1(2) . . . . ?
C14 C19 C18 C17 -1.4(2) . . . . ?
C8 N1 C1 C6 0.50(16) . . . . ?
C8 N1 C1 C2 -177.26(14) . . . . ?
C8 N1 C14 C15 55.06(19) . . . . ?
C8 N1 C14 C19 -124.53(15) . . . . ?
C6 C1 C2 C3 0.2(2) . . . . ?
C6 C5 C4 C3 0.2(2) . . . . ?
C15 C14 C19 C18 0.8(2) . . . . ?
C15 C16 C17 C18 0.5(2) . . . . ?
C2 C1 C6 C7 175.93(12) . . . . ?
C2 C1 C6 C5 -1.3(2) . . . . ?
C7 C6 C5 C4 -175.44(13) . . . . ?
C5 C6 C7 N2 64.58(18) . . . . ?
C5 C6 C7 C9 -54.1(2) . . . . ?
C5 C6 C7 C8 179.37(14) . . . . ?
C5 C4 C3 C2 -1.2(2) . . . . ?
C19 C14 C15 C16 0.4(2) . . . . ?
C19 C18 C17 C16 0.8(2) . . . . ?
C11 C10 C9 C009 -100.09(14) . . . . ?
C11 C10 C9 C7 138.58(12) . . . . ?
C12 O2 C009 O3 -3.38(19) . . . . ?
C12 O2 C009 C9 174.80(11) . . . . ?

_olex2_date_sample_data_collection 2017-03-28
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.280
_oxdiff_exptl_absorpt_empirical_full_min 0.665
