# Electronic Supplementary Material (ESI) for ChemComm.
# 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_16kaw98a
_database_code_depnum_ccdc_archive 'CCDC 1534592'
_audit_update_record             
;
2017-02-23 deposited with the CCDC.
2017-03-31 downloaded from the CCDC.
;


_audit_creation_method           SHELXL-2014/7
#_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H14 F3 N O, C16 H17 N O'
_chemical_formula_sum            'C32 H31 F3 N2 O2'
_chemical_formula_weight         532.59

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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.
;

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

_cell_length_a                   8.7183(13)
_cell_length_b                   18.007(2)
_cell_length_c                   9.5051(11)
_cell_angle_alpha                90
_cell_angle_beta                 106.811(8)
_cell_angle_gamma                90
_cell_volume                     1428.4(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7268
_cell_measurement_theta_min      2.45
_cell_measurement_theta_max      67.62
_exptl_crystal_description       'transparent plate'
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.238
_exptl_crystal_F_000             560
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.444
_exptl_crystal_size_mid          0.168
_exptl_crystal_size_min          0.098
_exptl_absorpt_coefficient_mu    0.748
_shelx_estimated_absorpt_T_min   0.732
_shelx_estimated_absorpt_T_max   0.930
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.591
_exptl_absorpt_correction_T_max  0.753
_exptl_absorpt_process_details   'SADABS-2014/7, Bruker AXS'
#_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.33
_diffrn_reflns_number            20723
_diffrn_reflns_av_unetI/netI     0.0612
_diffrn_reflns_av_R_equivalents  0.0734
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         4.860
_diffrn_reflns_theta_max         68.204
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_point_group_measured_fraction_full 0.973
_reflns_number_total             5088
_reflns_number_gt                3596
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.884
_reflns_Friedel_fraction_max     0.945
_reflns_Friedel_fraction_full    0.947

_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.
;

_computing_data_collection       'APEX2 (Bruker, 2013)'
_computing_cell_refinement       APEX2
_computing_data_reduction        
;
SADABS (Bruker, 2013) and XPREP (Bruker, 2013)
;
_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'XSEED (Barbour, 2001)'
_computing_publication_material  'XSEED (Barbour, 2001)'

_refine_special_details          
;
All nonhydrogen atoms were located in a succesive difference Fourier electron
 density maps and refined using anisotropic diplacement parameters. All C-H
 hydrogen atoms were placed in calculated positions with Uiso = 1.2xUeqiv
 (1.5Ueq for methyl groups) of the connected C atoms. Those H atoms attached
 to nitrogen were located in Fourier diff maps and assigned Uiso = 1.2xUeqiv
 with N-H bond distances restrained to 0.85(2) angstroms.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0845P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1305 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(2)
_chemical_absolute_configuration rmad
_refine_ls_number_reflns         5088
_refine_ls_number_parameters     363
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0712
_refine_ls_R_factor_gt           0.0515
_refine_ls_wR_factor_ref         0.1662
_refine_ls_wR_factor_gt          0.1446
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_restrained_S_all      1.073
_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_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
O1 O 0.7906(5) 0.8425(2) 0.3689(4) 0.0682(12) Uani 1 1 d . . . . .
O1A O 0.7876(5) 0.7502(2) 0.8692(4) 0.0619(10) Uani 1 1 d . . . . .
N1 N 0.7895(5) 0.7697(2) 0.1749(4) 0.0513(11) Uani 1 1 d D . . . .
N1A N 0.7779(5) 0.8211(2) 0.6689(4) 0.0495(11) Uani 1 1 d D . . . .
C9 C 0.5351(7) 0.7097(3) 0.1739(5) 0.0519(12) Uani 1 1 d . . . . .
C1A C 0.8047(6) 0.7575(3) 0.7454(5) 0.0451(11) Uani 1 1 d . . . . .
C8 C 0.7173(6) 0.7054(3) 0.2249(5) 0.0517(12) Uani 1 1 d . . . . .
H8 H 0.7528 0.7052 0.3348 0.062 Uiso 1 1 calc R U . . .
C1 C 0.8112(7) 0.8343(3) 0.2476(5) 0.0486(12) Uani 1 1 d . . . . .
C9A C 0.5277(6) 0.8834(3) 0.6748(5) 0.0488(12) Uani 1 1 d . . . . .
C8A C 0.7094(6) 0.8867(3) 0.7201(5) 0.0512(12) Uani 1 1 d . . . . .
H8A H 0.7488 0.8878 0.8299 0.061 Uiso 1 1 calc R U . . .
C2A C 0.8627(6) 0.6938(3) 0.6702(5) 0.0477(12) Uani 1 1 d . . . . .
C2 C 0.8673(7) 0.8979(3) 0.1728(5) 0.0520(13) Uani 1 1 d . . . . .
C3 C 1.0091(7) 0.8940(4) 0.1331(6) 0.0648(15) Uani 1 1 d . . . . .
H3 H 1.0709 0.8497 0.1508 0.078 Uiso 1 1 calc R U . . .
C11 C 0.2819(10) 0.6783(5) 0.2143(10) 0.090(2) Uani 1 1 d . . . . .
H11 H 0.2242 0.6551 0.2732 0.107 Uiso 1 1 calc R U . . .
C7A C 0.7833(7) 0.6260(3) 0.6408(6) 0.0599(15) Uani 1 1 d . . . . .
C3A C 1.0082(7) 0.7024(3) 0.6380(6) 0.0603(14) Uani 1 1 d . . . . .
H3A H 1.0636 0.7485 0.6554 0.072 Uiso 1 1 calc R U . . .
C7 C 0.7726(9) 0.9622(3) 0.1405(6) 0.0689(17) Uani 1 1 d . . . . .
C6 C 0.8269(13) 1.0215(4) 0.0709(8) 0.092(3) Uani 1 1 d . . . . .
H6 H 0.7643 1.0654 0.0475 0.111 Uiso 1 1 calc R U . . .
C15A C 0.7696(7) 0.9563(3) 0.6620(7) 0.0635(15) Uani 1 1 d . . . . .
H15A H 0.8862 0.9597 0.7030 0.095 Uiso 1 1 calc R U . . .
H15B H 0.7195 1.0002 0.6909 0.095 Uiso 1 1 calc R U . . .
H15C H 0.7418 0.9539 0.5545 0.095 Uiso 1 1 calc R U . . .
C15 C 0.7796(8) 0.6347(3) 0.1715(7) 0.0706(18) Uani 1 1 d . . . . .
H15D H 0.7596 0.6372 0.0647 0.106 Uiso 1 1 calc R U . . .
H15E H 0.7241 0.5916 0.1964 0.106 Uiso 1 1 calc R U . . .
H15F H 0.8950 0.6301 0.2191 0.106 Uiso 1 1 calc R U . . .
C10 C 0.4472(8) 0.6776(4) 0.2585(7) 0.0752(18) Uani 1 1 d . . . . .
H10 H 0.5021 0.6546 0.3490 0.090 Uiso 1 1 calc R U . . .
C16A C 0.6261(9) 0.6138(4) 0.6718(7) 0.0734(17) Uani 1 1 d . . . . .
C14A C 0.4388(8) 0.8504(4) 0.5469(7) 0.0761(19) Uani 1 1 d . . . . .
H14A H 0.4915 0.8272 0.4840 0.091 Uiso 1 1 calc R U . . .
C6A C 0.8486(11) 0.5680(3) 0.5813(7) 0.080(2) Uani 1 1 d . . . . .
H6A H 0.7923 0.5223 0.5602 0.097 Uiso 1 1 calc R U . . .
C14 C 0.4528(9) 0.7425(4) 0.0444(8) 0.084(2) Uani 1 1 d . . . . .
H14 H 0.5100 0.7641 -0.0165 0.101 Uiso 1 1 calc R U . . .
C10A C 0.4457(8) 0.9168(3) 0.7627(7) 0.0662(15) Uani 1 1 d . . . . .
H10A H 0.5039 0.9403 0.8516 0.079 Uiso 1 1 calc R U . . .
C4 C 1.0610(10) 0.9544(5) 0.0677(7) 0.088(2) Uani 1 1 d . . . . .
H4 H 1.1600 0.9523 0.0448 0.106 Uiso 1 1 calc R U . . .
C4A C 1.0718(9) 0.6419(5) 0.5793(8) 0.081(2) Uani 1 1 d . . . . .
H4A H 1.1711 0.6473 0.5579 0.098 Uiso 1 1 calc R U . . .
C5A C 0.9916(11) 0.5754(4) 0.5525(8) 0.090(2) Uani 1 1 d . . . . .
H5A H 1.0361 0.5347 0.5140 0.107 Uiso 1 1 calc R U . . .
C12 C 0.2003(9) 0.7127(4) 0.0845(10) 0.088(2) Uani 1 1 d . . . . .
H12 H 0.0865 0.7140 0.0539 0.105 Uiso 1 1 calc R U . . .
C12A C 0.1931(8) 0.8835(4) 0.5936(9) 0.0789(19) Uani 1 1 d . . . . .
H12A H 0.0793 0.8836 0.5645 0.095 Uiso 1 1 calc R U . . .
C5 C 0.9676(14) 1.0167(5) 0.0369(9) 0.100(3) Uani 1 1 d . . . . .
H5 H 1.0020 1.0577 -0.0093 0.120 Uiso 1 1 calc R U . . .
C13 C 0.2858(10) 0.7447(5) 0.0009(11) 0.106(3) Uani 1 1 d . . . . .
H13 H 0.2307 0.7688 -0.0883 0.127 Uiso 1 1 calc R U . . .
F2A F 0.6428(6) 0.5945(2) 0.8109(4) 0.1034(14) Uani 1 1 d . . . . .
C13A C 0.2735(9) 0.8507(4) 0.5088(9) 0.087(2) Uani 1 1 d . . . . .
H13A H 0.2147 0.8271 0.4202 0.104 Uiso 1 1 calc R U . . .
C16 C 0.6154(11) 0.9684(5) 0.1744(9) 0.109(3) Uani 1 1 d . . . . .
H16A H 0.5657 0.9193 0.1680 0.164 Uiso 1 1 calc R U . . .
H16B H 0.5444 1.0019 0.1034 0.164 Uiso 1 1 calc R U . . .
H16C H 0.6334 0.9883 0.2739 0.164 Uiso 1 1 calc R U . . .
F3A F 0.5317(5) 0.6745(2) 0.6443(4) 0.0925(11) Uani 1 1 d . . . . .
C11A C 0.2776(9) 0.9164(4) 0.7218(9) 0.083(2) Uani 1 1 d . . . . .
H11A H 0.2227 0.9390 0.7836 0.099 Uiso 1 1 calc R U . . .
F1A F 0.5398(6) 0.5607(3) 0.5865(4) 0.1150(16) Uani 1 1 d . . . . .
H1A H 0.769(5) 0.820(2) 0.577(3) 0.027(10) Uiso 1 1 d D . . . .
H1 H 0.811(6) 0.774(3) 0.092(4) 0.057(15) Uiso 1 1 d 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
O1 C1 1.226(6) . ?
O1A C1A 1.235(6) . ?
N1 C1 1.337(6) . ?
N1 C8 1.461(7) . ?
N1 H1 0.87(3) . ?
N1A C1A 1.340(6) . ?
N1A C8A 1.468(6) . ?
N1A H1A 0.85(2) . ?
C9 C14 1.367(8) . ?
C9 C10 1.388(8) . ?
C9 C8 1.523(8) . ?
C1A C2A 1.514(7) . ?
C8 C15 1.528(8) . ?
C8 H8 1.0000 . ?
C1 C2 1.503(8) . ?
C9A C14A 1.373(8) . ?
C9A C10A 1.385(8) . ?
C9A C8A 1.518(8) . ?
C8A C15A 1.524(8) . ?
C8A H8A 1.0000 . ?
C2A C7A 1.392(8) . ?
C2A C3A 1.397(8) . ?
C2 C3 1.396(8) . ?
C2 C7 1.403(8) . ?
C3 C4 1.391(10) . ?
C3 H3 0.9500 . ?
C11 C10 1.380(10) . ?
C11 C12 1.380(11) . ?
C11 H11 0.9500 . ?
C7A C6A 1.386(9) . ?
C7A C16A 1.499(9) . ?
C3A C4A 1.408(9) . ?
C3A H3A 0.9500 . ?
C7 C6 1.409(11) . ?
C7 C16 1.500(11) . ?
C6 C5 1.359(13) . ?
C6 H6 0.9500 . ?
C15A H15A 0.9800 . ?
C15A H15B 0.9800 . ?
C15A H15C 0.9800 . ?
C15 H15D 0.9800 . ?
C15 H15E 0.9800 . ?
C15 H15F 0.9800 . ?
C10 H10 0.9500 . ?
C16A F2A 1.334(7) . ?
C16A F1A 1.336(7) . ?
C16A F3A 1.348(9) . ?
C14A C13A 1.381(9) . ?
C14A H14A 0.9500 . ?
C6A C5A 1.358(11) . ?
C6A H6A 0.9500 . ?
C14 C13 1.394(10) . ?
C14 H14 0.9500 . ?
C10A C11A 1.403(10) . ?
C10A H10A 0.9500 . ?
C4 C5 1.368(13) . ?
C4 H4 0.9500 . ?
C4A C5A 1.374(12) . ?
C4A H4A 0.9500 . ?
C5A H5A 0.9500 . ?
C12 C13 1.365(12) . ?
C12 H12 0.9500 . ?
C12A C13A 1.347(10) . ?
C12A C11A 1.364(10) . ?
C12A H12A 0.9500 . ?
C5 H5 0.9500 . ?
C13 H13 0.9500 . ?
C13A H13A 0.9500 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C11A H11A 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C8 122.1(4) . . ?
C1 N1 H1 111(4) . . ?
C8 N1 H1 127(4) . . ?
C1A N1A C8A 122.0(4) . . ?
C1A N1A H1A 119(3) . . ?
C8A N1A H1A 116(3) . . ?
C14 C9 C10 117.9(6) . . ?
C14 C9 C8 122.4(5) . . ?
C10 C9 C8 119.6(5) . . ?
O1A C1A N1A 123.9(5) . . ?
O1A C1A C2A 121.2(5) . . ?
N1A C1A C2A 114.9(4) . . ?
N1 C8 C9 111.3(4) . . ?
N1 C8 C15 108.9(4) . . ?
C9 C8 C15 112.0(5) . . ?
N1 C8 H8 108.1 . . ?
C9 C8 H8 108.1 . . ?
C15 C8 H8 108.1 . . ?
O1 C1 N1 123.6(5) . . ?
O1 C1 C2 120.6(5) . . ?
N1 C1 C2 115.8(4) . . ?
C14A C9A C10A 117.7(5) . . ?
C14A C9A C8A 123.0(5) . . ?
C10A C9A C8A 119.3(5) . . ?
N1A C8A C9A 111.4(4) . . ?
N1A C8A C15A 109.0(4) . . ?
C9A C8A C15A 111.7(5) . . ?
N1A C8A H8A 108.2 . . ?
C9A C8A H8A 108.2 . . ?
C15A C8A H8A 108.2 . . ?
C7A C2A C3A 118.9(5) . . ?
C7A C2A C1A 123.0(5) . . ?
C3A C2A C1A 117.9(5) . . ?
C3 C2 C7 119.6(5) . . ?
C3 C2 C1 121.6(5) . . ?
C7 C2 C1 118.8(5) . . ?
C4 C3 C2 120.6(6) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C10 C11 C12 120.0(7) . . ?
C10 C11 H11 120.0 . . ?
C12 C11 H11 120.0 . . ?
C6A C7A C2A 120.2(6) . . ?
C6A C7A C16A 118.5(6) . . ?
C2A C7A C16A 121.3(5) . . ?
C2A C3A C4A 119.2(6) . . ?
C2A C3A H3A 120.4 . . ?
C4A C3A H3A 120.4 . . ?
C2 C7 C6 118.2(7) . . ?
C2 C7 C16 122.1(6) . . ?
C6 C7 C16 119.7(7) . . ?
C5 C6 C7 120.9(7) . . ?
C5 C6 H6 119.6 . . ?
C7 C6 H6 119.6 . . ?
C8A C15A H15A 109.5 . . ?
C8A C15A H15B 109.5 . . ?
H15A C15A H15B 109.5 . . ?
C8A C15A H15C 109.5 . . ?
H15A C15A H15C 109.5 . . ?
H15B C15A H15C 109.5 . . ?
C8 C15 H15D 109.5 . . ?
C8 C15 H15E 109.5 . . ?
H15D C15 H15E 109.5 . . ?
C8 C15 H15F 109.5 . . ?
H15D C15 H15F 109.5 . . ?
H15E C15 H15F 109.5 . . ?
C11 C10 C9 121.5(7) . . ?
C11 C10 H10 119.2 . . ?
C9 C10 H10 119.2 . . ?
F2A C16A F1A 107.3(5) . . ?
F2A C16A F3A 106.8(6) . . ?
F1A C16A F3A 104.9(6) . . ?
F2A C16A C7A 112.9(6) . . ?
F1A C16A C7A 111.8(6) . . ?
F3A C16A C7A 112.6(5) . . ?
C9A C14A C13A 120.6(6) . . ?
C9A C14A H14A 119.7 . . ?
C13A C14A H14A 119.7 . . ?
C5A C6A C7A 121.2(7) . . ?
C5A C6A H6A 119.4 . . ?
C7A C6A H6A 119.4 . . ?
C9 C14 C13 120.7(7) . . ?
C9 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C9A C10A C11A 120.7(6) . . ?
C9A C10A H10A 119.7 . . ?
C11A C10A H10A 119.7 . . ?
C5 C4 C3 119.1(7) . . ?
C5 C4 H4 120.4 . . ?
C3 C4 H4 120.4 . . ?
C5A C4A C3A 120.7(7) . . ?
C5A C4A H4A 119.6 . . ?
C3A C4A H4A 119.6 . . ?
C6A C5A C4A 119.7(6) . . ?
C6A C5A H5A 120.2 . . ?
C4A C5A H5A 120.2 . . ?
C13 C12 C11 118.9(7) . . ?
C13 C12 H12 120.6 . . ?
C11 C12 H12 120.6 . . ?
C13A C12A C11A 119.0(7) . . ?
C13A C12A H12A 120.5 . . ?
C11A C12A H12A 120.5 . . ?
C6 C5 C4 121.6(7) . . ?
C6 C5 H5 119.2 . . ?
C4 C5 H5 119.2 . . ?
C12 C13 C14 121.0(7) . . ?
C12 C13 H13 119.5 . . ?
C14 C13 H13 119.5 . . ?
C12A C13A C14A 121.9(7) . . ?
C12A C13A H13A 119.0 . . ?
C14A C13A H13A 119.0 . . ?
C7 C16 H16A 109.5 . . ?
C7 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C7 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C12A C11A C10A 120.1(6) . . ?
C12A C11A H11A 120.0 . . ?
C10A C11A H11A 120.0 . . ?

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
C8A N1A C1A O1A -6.3(8) . . . . ?
C8A N1A C1A C2A 175.1(4) . . . . ?
C1 N1 C8 C9 83.2(6) . . . . ?
C1 N1 C8 C15 -152.8(5) . . . . ?
C14 C9 C8 N1 31.9(8) . . . . ?
C10 C9 C8 N1 -150.0(5) . . . . ?
C14 C9 C8 C15 -90.3(7) . . . . ?
C10 C9 C8 C15 87.8(6) . . . . ?
C8 N1 C1 O1 8.8(9) . . . . ?
C8 N1 C1 C2 -172.5(5) . . . . ?
C1A N1A C8A C9A -85.0(6) . . . . ?
C1A N1A C8A C15A 151.3(5) . . . . ?
C14A C9A C8A N1A -32.3(7) . . . . ?
C10A C9A C8A N1A 149.8(5) . . . . ?
C14A C9A C8A C15A 89.9(7) . . . . ?
C10A C9A C8A C15A -88.0(6) . . . . ?
O1A C1A C2A C7A 58.5(8) . . . . ?
N1A C1A C2A C7A -122.9(6) . . . . ?
O1A C1A C2A C3A -117.2(6) . . . . ?
N1A C1A C2A C3A 61.4(6) . . . . ?
O1 C1 C2 C3 120.9(6) . . . . ?
N1 C1 C2 C3 -57.8(7) . . . . ?
O1 C1 C2 C7 -60.2(8) . . . . ?
N1 C1 C2 C7 121.1(6) . . . . ?
C7 C2 C3 C4 2.9(9) . . . . ?
C1 C2 C3 C4 -178.2(5) . . . . ?
C3A C2A C7A C6A 0.3(8) . . . . ?
C1A C2A C7A C6A -175.3(5) . . . . ?
C3A C2A C7A C16A -179.4(5) . . . . ?
C1A C2A C7A C16A 4.9(8) . . . . ?
C7A C2A C3A C4A -1.1(8) . . . . ?
C1A C2A C3A C4A 174.8(5) . . . . ?
C3 C2 C7 C6 -1.3(8) . . . . ?
C1 C2 C7 C6 179.8(5) . . . . ?
C3 C2 C7 C16 177.2(6) . . . . ?
C1 C2 C7 C16 -1.7(8) . . . . ?
C2 C7 C6 C5 -0.4(10) . . . . ?
C16 C7 C6 C5 -178.9(7) . . . . ?
C12 C11 C10 C9 -1.2(12) . . . . ?
C14 C9 C10 C11 0.1(10) . . . . ?
C8 C9 C10 C11 -178.1(6) . . . . ?
C6A C7A C16A F2A 95.9(7) . . . . ?
C2A C7A C16A F2A -84.3(7) . . . . ?
C6A C7A C16A F1A -25.1(8) . . . . ?
C2A C7A C16A F1A 154.6(6) . . . . ?
C6A C7A C16A F3A -143.0(6) . . . . ?
C2A C7A C16A F3A 36.7(7) . . . . ?
C10A C9A C14A C13A -0.3(10) . . . . ?
C8A C9A C14A C13A -178.2(6) . . . . ?
C2A C7A C6A C5A 1.1(10) . . . . ?
C16A C7A C6A C5A -179.2(6) . . . . ?
C10 C9 C14 C13 1.2(11) . . . . ?
C8 C9 C14 C13 179.4(7) . . . . ?
C14A C9A C10A C11A 0.3(9) . . . . ?
C8A C9A C10A C11A 178.4(5) . . . . ?
C2 C3 C4 C5 -2.8(10) . . . . ?
C2A C3A C4A C5A 0.6(10) . . . . ?
C7A C6A C5A C4A -1.6(11) . . . . ?
C3A C4A C5A C6A 0.8(11) . . . . ?
C10 C11 C12 C13 0.9(12) . . . . ?
C7 C6 C5 C4 0.5(12) . . . . ?
C3 C4 C5 C6 1.1(12) . . . . ?
C11 C12 C13 C14 0.4(14) . . . . ?
C9 C14 C13 C12 -1.5(14) . . . . ?
C11A C12A C13A C14A -0.9(11) . . . . ?
C9A C14A C13A C12A 0.6(12) . . . . ?
C13A C12A C11A C10A 1.0(10) . . . . ?
C9A C10A C11A C12A -0.7(10) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1A H1A O1 0.85(2) 2.08(3) 2.911(5) 164(4) .
N1 H1 O1A 0.87(3) 2.11(3) 2.923(5) 156(5) 1_554

_refine_diff_density_max         0.157
_refine_diff_density_min         -0.172
_refine_diff_density_rms         0.039


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: 1:1 hexanes:dichloromethane '
####################################################################### 
# 
# 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_16kaw105
_database_code_depnum_ccdc_archive 'CCDC 1534593'
_audit_update_record             
;
2017-02-23 deposited with the CCDC.
2017-03-31 downloaded from the CCDC.
;


_audit_creation_method           SHELXL-2014/7
#_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H14 N2 O3, C15 H13 Br N O'
_chemical_formula_sum            'C30 H28 Br N3 O4'
_chemical_formula_weight         574.46

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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.
;

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

_cell_length_a                   8.2953(5)
_cell_length_b                   9.5761(5)
_cell_length_c                   17.2423(9)
_cell_angle_alpha                90
_cell_angle_beta                 101.342(3)
_cell_angle_gamma                90
_cell_volume                     1342.92(13)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    4629
_cell_measurement_theta_min      2.61
_cell_measurement_theta_max      66.27

_exptl_crystal_description       'transparent plate'
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.421
_exptl_crystal_F_000             592
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.148
_exptl_crystal_size_mid          0.109
_exptl_crystal_size_min          0.034
_exptl_absorpt_coefficient_mu    2.420
_shelx_estimated_absorpt_T_min   0.716
_shelx_estimated_absorpt_T_max   0.922
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.587
_exptl_absorpt_correction_T_max  0.753
_exptl_absorpt_process_details   'SADABS-2014/7, Bruker AXS'
#_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.33
_diffrn_reflns_number            20609
_diffrn_reflns_av_unetI/netI     0.0867
_diffrn_reflns_av_R_equivalents  0.1097
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.614
_diffrn_reflns_theta_max         68.246
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_point_group_measured_fraction_full 0.986
_reflns_number_total             4825
_reflns_number_gt                3810
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.849
_reflns_Friedel_fraction_max     0.966
_reflns_Friedel_fraction_full    0.969

_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.
;

_computing_data_collection       'APEX2 (Bruker, 2013)'
_computing_cell_refinement       APEX2
_computing_data_reduction        
;
SADABS (Bruker, 2013) and XPREP (Bruker, 2013)
;
_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'XSEED (Barbour, 2001)'
_computing_publication_material  'XSEED (Barbour, 2001)'

_refine_special_details          
;
All nonhydrogen atoms were located in a succesive difference Fourier electron
 density maps and refined using anisotropic diplacement parameters. All C-H
 hydrogen atoms were placed in calculated positions with Uiso = 1.2xUeqiv
 (1.5Ueq for methyl groups) of the connected C atoms. Those H atoms attached
 to nitrogen were located in Fourier diff maps and assigned Uiso = 1.2xUeqiv
 with N-H bond distances restrained to 0.85(2) angstroms. H1A was further
 restrained with H1A..C1A and H1A..C8A distances fixed to 1.86(2) and
 1.97(2) angstroms, respecitvely.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0401P)²+4.1799P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1318 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.10(2)
_chemical_absolute_configuration rmad
_refine_ls_number_reflns         4825
_refine_ls_number_parameters     351
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.0967
_refine_ls_R_factor_gt           0.0737
_refine_ls_wR_factor_ref         0.1652
_refine_ls_wR_factor_gt          0.1536
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_restrained_S_all      1.088
_refine_ls_shift/su_max          0.057
_refine_ls_shift/su_mean         0.002

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
Br1A Br 0.67707(14) 0.13773(15) 0.35074(7) 0.0455(3) Uani 1 1 d . . . . .
O1 O 0.5044(11) 0.1635(7) 0.0170(4) 0.042(2) Uani 1 1 d . . . . .
O2 O 0.8419(13) -0.2002(10) 0.1852(6) 0.064(3) Uani 1 1 d . . . . .
O3 O 0.8123(12) -0.0056(9) 0.1230(5) 0.049(2) Uani 1 1 d . . . . .
O1A O 0.9832(11) -0.1244(8) 0.4720(4) 0.042(2) Uani 1 1 d . . . . .
N1 N 0.5674(13) -0.0517(9) -0.0253(5) 0.035(2) Uani 1 1 d D . . . .
H1 H 0.559(14) -0.140(3) -0.022(7) 0.042 Uiso 1 1 d D U . . .
N2 N 0.7561(13) -0.1051(10) 0.1554(5) 0.041(2) Uani 1 1 d . . . . .
N1A N 0.9375(14) 0.0839(8) 0.5231(5) 0.030(2) Uani 1 1 d D . . . .
H1A H 0.932(14) 0.169(3) 0.514(4) 0.036 Uiso 1 1 d D U . . .
C1 C 0.5162(16) 0.0323(11) 0.0251(6) 0.034(3) Uani 1 1 d . . . . .
C2 C 0.4691(16) -0.0361(10) 0.0966(6) 0.036(3) Uani 1 1 d . . . . .
C3 C 0.3078(16) -0.0330(11) 0.1033(6) 0.037(3) Uani 1 1 d . . . . .
H3 H 0.2296 0.0146 0.0647 0.045 Uiso 1 1 calc R U . . .
C4 C 0.2564(17) -0.0996(12) 0.1668(7) 0.044(3) Uani 1 1 d . . . . .
H4 H 0.1442 -0.0961 0.1714 0.052 Uiso 1 1 calc R U . . .
C5 C 0.371(2) -0.1713(13) 0.2236(6) 0.053(4) Uani 1 1 d . . . . .
H5 H 0.3359 -0.2186 0.2658 0.064 Uiso 1 1 calc R U . . .
C6 C 0.5320(18) -0.1729(11) 0.2180(7) 0.041(3) Uani 1 1 d . . . . .
H6 H 0.6095 -0.2209 0.2568 0.049 Uiso 1 1 calc R U . . .
C7 C 0.5849(17) -0.1046(12) 0.1558(6) 0.036(3) Uani 1 1 d . . . . .
C8 C 0.6357(16) -0.0073(11) -0.0924(6) 0.038(3) Uani 1 1 d . . . . .
H8 H 0.6347 0.0971 -0.0934 0.045 Uiso 1 1 calc R U . . .
C9 C 0.8096(15) -0.0537(11) -0.0847(6) 0.035(3) Uani 1 1 d . . . . .
C10 C 0.9226(16) 0.0282(12) -0.1150(6) 0.042(3) Uani 1 1 d . . . . .
H10 H 0.8908 0.1178 -0.1362 0.050 Uiso 1 1 calc R U . . .
C11 C 1.0817(15) -0.0202(12) -0.1144(6) 0.039(3) Uani 1 1 d . . . . .
H11 H 1.1553 0.0359 -0.1367 0.047 Uiso 1 1 calc R U . . .
C12 C 1.1343(17) -0.1488(13) -0.0817(7) 0.046(3) Uani 1 1 d . . . . .
H12 H 1.2425 -0.1819 -0.0811 0.055 Uiso 1 1 calc R U . . .
C13 C 1.0244(18) -0.2257(12) -0.0505(6) 0.044(3) Uani 1 1 d . . . . .
H13 H 1.0586 -0.3133 -0.0269 0.053 Uiso 1 1 calc R U . . .
C14 C 0.8673(16) -0.1822(11) -0.0516(6) 0.035(3) Uani 1 1 d . . . . .
H14 H 0.7954 -0.2405 -0.0295 0.042 Uiso 1 1 calc R U . . .
C15 C 0.5265(18) -0.0582(13) -0.1682(7) 0.050(3) Uani 1 1 d . . . . .
H15A H 0.5297 -0.1604 -0.1701 0.075 Uiso 1 1 calc R U . . .
H15B H 0.5659 -0.0198 -0.2138 0.075 Uiso 1 1 calc R U . . .
H15C H 0.4133 -0.0272 -0.1698 0.075 Uiso 1 1 calc R U . . .
C1A C 0.9815(13) 0.0013(10) 0.4689(6) 0.027(2) Uani 1 1 d D . . . .
C2A C 1.0179(13) 0.0756(10) 0.3971(5) 0.026(2) Uani 1 1 d . . . . .
C3A C 1.1819(14) 0.0750(11) 0.3862(6) 0.033(3) Uani 1 1 d . . . . .
H3A H 1.2649 0.0294 0.4234 0.040 Uiso 1 1 calc R U . . .
C4A C 1.2220(13) 0.1411(17) 0.3211(6) 0.041(2) Uani 1 1 d . . . . .
H4A H 1.3333 0.1446 0.3151 0.049 Uiso 1 1 calc R U . . .
C5A C 1.1001(17) 0.2022(12) 0.2646(6) 0.040(3) Uani 1 1 d . . . . .
H5A H 1.1280 0.2442 0.2191 0.048 Uiso 1 1 calc R U . . .
C6A C 0.9373(15) 0.2024(11) 0.2741(6) 0.036(3) Uani 1 1 d . . . . .
H6A H 0.8534 0.2441 0.2356 0.043 Uiso 1 1 calc R U . . .
C7A C 0.9002(12) 0.1397(14) 0.3416(5) 0.033(2) Uani 1 1 d . . . . .
C8A C 0.8705(14) 0.0345(10) 0.5911(5) 0.030(2) Uani 1 1 d D . . . .
H8A H 0.8720 -0.0699 0.5909 0.037 Uiso 1 1 calc R U . . .
C9A C 0.6968(15) 0.0810(11) 0.5866(6) 0.027(3) Uani 1 1 d . . . . .
C10A C 0.6442(16) 0.2164(11) 0.5645(7) 0.033(3) Uani 1 1 d . . . . .
H10A H 0.7205 0.2802 0.5496 0.040 Uiso 1 1 calc R U . . .
C11A C 0.4899(16) 0.2599(11) 0.5634(6) 0.034(3) Uani 1 1 d . . . . .
H11A H 0.4598 0.3531 0.5480 0.040 Uiso 1 1 calc R U . . .
C12A C 0.3751(14) 0.1719(9) 0.5843(6) 0.029(2) Uani 1 1 d . . . . .
H12A H 0.2665 0.2031 0.5845 0.035 Uiso 1 1 calc R U . . .
C13A C 0.4226(16) 0.0365(12) 0.6050(7) 0.038(3) Uani 1 1 d . . . . .
H13A H 0.3442 -0.0272 0.6180 0.045 Uiso 1 1 calc R U . . .
C14A C 0.5786(15) -0.0072(11) 0.6071(6) 0.033(3) Uani 1 1 d . . . . .
H14A H 0.6081 -0.1003 0.6230 0.039 Uiso 1 1 calc R U . . .
C15A C 0.9832(14) 0.0851(12) 0.6689(6) 0.040(3) Uani 1 1 d . . . . .
H15D H 1.0973 0.0592 0.6686 0.059 Uiso 1 1 calc R U . . .
H15E H 0.9483 0.0412 0.7143 0.059 Uiso 1 1 calc R U . . .
H15F H 0.9749 0.1868 0.6730 0.059 Uiso 1 1 calc R U . . .


_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
Br1A C7A 1.888(10) . ?
O1 C1 1.266(14) . ?
O2 N2 1.206(13) . ?
O3 N2 1.240(12) . ?
O1A C1A 1.204(12) . ?
N1 C1 1.314(14) . ?
N1 C8 1.449(13) . ?
N1 H1 0.85(3) . ?
N2 C7 1.422(16) . ?
N1A C1A 1.328(12) . ?
N1A C8A 1.472(12) . ?
N1A H1A 0.83(2) . ?
C1 C2 1.513(15) . ?
C2 C3 1.366(17) . ?
C2 C7 1.417(16) . ?
C3 C4 1.404(16) . ?
C3 H3 0.9500 . ?
C4 C5 1.401(19) . ?
C4 H4 0.9500 . ?
C5 C6 1.36(2) . ?
C5 H5 0.9500 . ?
C6 C7 1.399(16) . ?
C6 H6 0.9500 . ?
C8 C9 1.491(17) . ?
C8 C15 1.518(16) . ?
C8 H8 1.0000 . ?
C9 C10 1.399(16) . ?
C9 C14 1.401(14) . ?
C10 C11 1.397(17) . ?
C10 H10 0.9500 . ?
C11 C12 1.389(17) . ?
C11 H11 0.9500 . ?
C12 C13 1.361(18) . ?
C12 H12 0.9500 . ?
C13 C14 1.365(18) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C1A C2A 1.509(14) . ?
C2A C7A 1.371(13) . ?
C2A C3A 1.410(15) . ?
C3A C4A 1.385(15) . ?
C3A H3A 0.9500 . ?
C4A C5A 1.388(16) . ?
C4A H4A 0.9500 . ?
C5A C6A 1.392(17) . ?
C5A H5A 0.9500 . ?
C6A C7A 1.396(14) . ?
C6A H6A 0.9500 . ?
C8A C9A 1.495(16) . ?
C8A C15A 1.554(14) . ?
C8A H8A 1.0000 . ?
C9A C14A 1.392(16) . ?
C9A C10A 1.398(14) . ?
C10A C11A 1.342(17) . ?
C10A H10A 0.9500 . ?
C11A C12A 1.371(16) . ?
C11A H11A 0.9500 . ?
C12A C13A 1.382(16) . ?
C12A H12A 0.9500 . ?
C13A C14A 1.354(17) . ?
C13A H13A 0.9500 . ?
C14A H14A 0.9500 . ?
C15A H15D 0.9800 . ?
C15A H15E 0.9800 . ?
C15A H15F 0.9800 . ?

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
C1 N1 C8 125.2(9) . . ?
C1 N1 H1 122(8) . . ?
C8 N1 H1 113(8) . . ?
O2 N2 O3 122.0(11) . . ?
O2 N2 C7 120.4(11) . . ?
O3 N2 C7 117.6(10) . . ?
C1A N1A C8A 124.6(8) . . ?
C1A N1A H1A 118(3) . . ?
C8A N1A H1A 116(3) . . ?
O1 C1 N1 124.2(10) . . ?
O1 C1 C2 119.5(10) . . ?
N1 C1 C2 116.3(9) . . ?
C3 C2 C7 119.0(10) . . ?
C3 C2 C1 118.3(10) . . ?
C7 C2 C1 122.7(11) . . ?
C2 C3 C4 120.6(12) . . ?
C2 C3 H3 119.7 . . ?
C4 C3 H3 119.7 . . ?
C5 C4 C3 119.9(13) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C6 C5 C4 119.8(11) . . ?
C6 C5 H5 120.1 . . ?
C4 C5 H5 120.1 . . ?
C5 C6 C7 120.6(13) . . ?
C5 C6 H6 119.7 . . ?
C7 C6 H6 119.7 . . ?
C6 C7 C2 119.9(12) . . ?
C6 C7 N2 117.8(11) . . ?
C2 C7 N2 122.3(10) . . ?
N1 C8 C9 111.5(9) . . ?
N1 C8 C15 109.5(10) . . ?
C9 C8 C15 112.6(9) . . ?
N1 C8 H8 107.7 . . ?
C9 C8 H8 107.7 . . ?
C15 C8 H8 107.7 . . ?
C10 C9 C14 116.4(11) . . ?
C10 C9 C8 120.5(10) . . ?
C14 C9 C8 123.0(10) . . ?
C11 C10 C9 120.8(10) . . ?
C11 C10 H10 119.6 . . ?
C9 C10 H10 119.6 . . ?
C12 C11 C10 121.2(11) . . ?
C12 C11 H11 119.4 . . ?
C10 C11 H11 119.4 . . ?
C13 C12 C11 117.3(13) . . ?
C13 C12 H12 121.3 . . ?
C11 C12 H12 121.3 . . ?
C12 C13 C14 122.7(11) . . ?
C12 C13 H13 118.6 . . ?
C14 C13 H13 118.6 . . ?
C13 C14 C9 121.5(11) . . ?
C13 C14 H14 119.2 . . ?
C9 C14 H14 119.2 . . ?
C8 C15 H15A 109.5 . . ?
C8 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C8 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O1A C1A N1A 124.5(10) . . ?
O1A C1A C2A 120.4(9) . . ?
N1A C1A C2A 115.0(8) . . ?
C7A C2A C3A 118.8(9) . . ?
C7A C2A C1A 123.7(9) . . ?
C3A C2A C1A 117.5(9) . . ?
C4A C3A C2A 119.9(11) . . ?
C4A C3A H3A 120.1 . . ?
C2A C3A H3A 120.1 . . ?
C3A C4A C5A 120.2(11) . . ?
C3A C4A H4A 119.9 . . ?
C5A C4A H4A 119.9 . . ?
C4A C5A C6A 120.5(10) . . ?
C4A C5A H5A 119.7 . . ?
C6A C5A H5A 119.7 . . ?
C5A C6A C7A 118.4(10) . . ?
C5A C6A H6A 120.8 . . ?
C7A C6A H6A 120.8 . . ?
C2A C7A C6A 122.1(10) . . ?
C2A C7A Br1A 120.8(7) . . ?
C6A C7A Br1A 117.0(8) . . ?
N1A C8A C9A 111.9(8) . . ?
N1A C8A C15A 109.3(9) . . ?
C9A C8A C15A 111.3(8) . . ?
N1A C8A H8A 108.1 . . ?
C9A C8A H8A 108.1 . . ?
C15A C8A H8A 108.1 . . ?
C14A C9A C10A 115.8(12) . . ?
C14A C9A C8A 121.7(9) . . ?
C10A C9A C8A 122.5(11) . . ?
C11A C10A C9A 122.5(12) . . ?
C11A C10A H10A 118.7 . . ?
C9A C10A H10A 118.7 . . ?
C10A C11A C12A 121.0(10) . . ?
C10A C11A H11A 119.5 . . ?
C12A C11A H11A 119.5 . . ?
C11A C12A C13A 117.9(11) . . ?
C11A C12A H12A 121.1 . . ?
C13A C12A H12A 121.1 . . ?
C14A C13A C12A 121.3(12) . . ?
C14A C13A H13A 119.4 . . ?
C12A C13A H13A 119.4 . . ?
C13A C14A C9A 121.5(10) . . ?
C13A C14A H14A 119.2 . . ?
C9A C14A H14A 119.2 . . ?
C8A C15A H15D 109.5 . . ?
C8A C15A H15E 109.5 . . ?
H15D C15A H15E 109.5 . . ?
C8A C15A H15F 109.5 . . ?
H15D C15A H15F 109.5 . . ?
H15E C15A H15F 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
C8 N1 C1 O1 7(2) . . . . ?
C8 N1 C1 C2 -172.6(11) . . . . ?
O1 C1 C2 C3 66.9(15) . . . . ?
N1 C1 C2 C3 -113.0(12) . . . . ?
O1 C1 C2 C7 -114.2(13) . . . . ?
N1 C1 C2 C7 65.9(14) . . . . ?
C7 C2 C3 C4 -1.5(15) . . . . ?
C1 C2 C3 C4 177.5(9) . . . . ?
C2 C3 C4 C5 -0.7(16) . . . . ?
C3 C4 C5 C6 1.7(17) . . . . ?
C4 C5 C6 C7 -0.5(17) . . . . ?
C5 C6 C7 C2 -1.7(16) . . . . ?
C5 C6 C7 N2 177.2(10) . . . . ?
C3 C2 C7 C6 2.7(15) . . . . ?
C1 C2 C7 C6 -176.2(9) . . . . ?
C3 C2 C7 N2 -176.2(9) . . . . ?
C1 C2 C7 N2 4.9(15) . . . . ?
O2 N2 C7 C6 28.9(15) . . . . ?
O3 N2 C7 C6 -151.7(10) . . . . ?
O2 N2 C7 C2 -152.2(11) . . . . ?
O3 N2 C7 C2 27.2(14) . . . . ?
C1 N1 C8 C9 117.1(12) . . . . ?
C1 N1 C8 C15 -117.7(13) . . . . ?
N1 C8 C9 C10 -147.0(10) . . . . ?
C15 C8 C9 C10 89.6(13) . . . . ?
N1 C8 C9 C14 36.6(14) . . . . ?
C15 C8 C9 C14 -86.9(13) . . . . ?
C14 C9 C10 C11 2.4(15) . . . . ?
C8 C9 C10 C11 -174.3(10) . . . . ?
C9 C10 C11 C12 -2.0(16) . . . . ?
C10 C11 C12 C13 0.1(16) . . . . ?
C11 C12 C13 C14 1.2(17) . . . . ?
C12 C13 C14 C9 -0.6(17) . . . . ?
C10 C9 C14 C13 -1.2(16) . . . . ?
C8 C9 C14 C13 175.4(10) . . . . ?
C8A N1A C1A O1A -5.7(19) . . . . ?
C8A N1A C1A C2A 169.5(10) . . . . ?
O1A C1A C2A C7A 106.1(13) . . . . ?
N1A C1A C2A C7A -69.3(14) . . . . ?
O1A C1A C2A C3A -72.1(13) . . . . ?
N1A C1A C2A C3A 112.4(11) . . . . ?
C7A C2A C3A C4A 1.3(15) . . . . ?
C1A C2A C3A C4A 179.7(10) . . . . ?
C2A C3A C4A C5A -3.0(19) . . . . ?
C3A C4A C5A C6A 2.4(19) . . . . ?
C4A C5A C6A C7A 0.0(17) . . . . ?
C3A C2A C7A C6A 1.0(16) . . . . ?
C1A C2A C7A C6A -177.2(10) . . . . ?
C3A C2A C7A Br1A 177.5(8) . . . . ?
C1A C2A C7A Br1A -0.7(14) . . . . ?
C5A C6A C7A C2A -1.7(17) . . . . ?
C5A C6A C7A Br1A -178.3(8) . . . . ?
C1A N1A C8A C9A -115.0(12) . . . . ?
C1A N1A C8A C15A 121.3(12) . . . . ?
N1A C8A C9A C14A 139.2(10) . . . . ?
C15A C8A C9A C14A -98.2(11) . . . . ?
N1A C8A C9A C10A -43.4(13) . . . . ?
C15A C8A C9A C10A 79.3(12) . . . . ?
C14A C9A C10A C11A 0.4(16) . . . . ?
C8A C9A C10A C11A -177.2(10) . . . . ?
C9A C10A C11A C12A -0.1(17) . . . . ?
C10A C11A C12A C13A -1.1(16) . . . . ?
C11A C12A C13A C14A 2.0(16) . . . . ?
C12A C13A C14A C9A -1.7(17) . . . . ?
C10A C9A C14A C13A 0.5(15) . . . . ?
C8A C9A C14A C13A 178.1(10) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O1 0.85(3) 1.96(4) 2.801(11) 169(12) 2_645
N1A H1A O1A 0.83(2) 2.10(6) 2.868(11) 154(12) 2_756

_refine_diff_density_max         1.047
_refine_diff_density_min         -0.821
_refine_diff_density_rms         0.100



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: 1:1 hexanes:dichloromethane '
####################################################################### 
# 
# 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_16kaw96
_database_code_depnum_ccdc_archive 'CCDC 1534589'
_audit_update_record             
;
2017-02-23 deposited with the CCDC.
2017-03-31 downloaded from the CCDC.
;


_audit_creation_method           SHELXL-2014/7
#_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        '(S)-N-(2-Methoxybenzoyl)methylbenzylamine '
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H17 N O2'
_chemical_formula_sum            'C16 H17 N O2'
_chemical_formula_weight         255.30

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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'

_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.
;

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                   5.8757(10)
_cell_length_b                   14.464(2)
_cell_length_c                   15.887(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1350.2(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3829
_cell_measurement_theta_min      3.06
_cell_measurement_theta_max      68.23
_exptl_crystal_description       'transparent blocks'
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.256
_exptl_crystal_F_000             544
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.314
_exptl_crystal_size_mid          0.145
_exptl_crystal_size_min          0.056
_exptl_absorpt_coefficient_mu    0.661
_shelx_estimated_absorpt_T_min   0.819
_shelx_estimated_absorpt_T_max   0.964
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.669
_exptl_absorpt_correction_T_max  0.753
_exptl_absorpt_process_details   'SADABS-2014/7, Bruker AXS'
#_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.33
_diffrn_reflns_number            5676
_diffrn_reflns_av_unetI/netI     0.0456
_diffrn_reflns_av_R_equivalents  0.0381
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         4.133
_diffrn_reflns_theta_max         68.222
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measured_fraction_theta_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.873
#_diffrn_reflns_point_group_measured_fraction_full 0.878
_reflns_number_total             2162
_reflns_number_gt                1911
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.516
_reflns_Friedel_fraction_max     0.724
_reflns_Friedel_fraction_full    0.731

_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.
;

_computing_data_collection       'APEX2 (Bruker, 2013)'
_computing_cell_refinement       APEX2
_computing_data_reduction        
;
SADABS (Bruker, 2013) and XPREP (Bruker, 2013)
;
_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'XSEED (Barbour, 2001)'
_computing_publication_material  'XSEED (Barbour, 2001)'

_refine_special_details          
;
All nonhydrogen atoms were located in a succesive difference Fourier electron
 density maps and refined using anisotropic diplacement parameters. All C-H
 hydrogen atoms were placed in calculated positions with Uiso = 1.2xUeqiv
 (1.5Ueq for methyl groups) of the connected C atoms. Those H atoms attached
 to nitrogen were located in Fourier diff maps and assigned Uiso = 1.2xUeqiv
 with N-H bond distances restrained to 0.85(2) angstroms.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0420P)²+0.0008P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 589 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(2)
_chemical_absolute_configuration rmad
_refine_ls_number_reflns         2162
_refine_ls_number_parameters     178
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0435
_refine_ls_R_factor_gt           0.0371
_refine_ls_wR_factor_ref         0.0893
_refine_ls_wR_factor_gt          0.0852
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_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_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
O1 O 0.8263(3) 0.90276(12) 0.75317(11) 0.0327(5) Uani 1 1 d . . . . .
O2 O 0.7870(3) 0.63786(11) 0.65757(11) 0.0293(4) Uani 1 1 d . . . . .
N1 N 0.9274(4) 0.81262(14) 0.64285(14) 0.0248(5) Uani 1 1 d D . . . .
H1 H 0.922(5) 0.7548(14) 0.6251(18) 0.051(10) Uiso 1 1 d D . . . .
C1 C 0.8026(4) 0.83105(16) 0.71278(16) 0.0240(6) Uani 1 1 d . . . . .
C2 C 0.6251(4) 0.76071(16) 0.73704(16) 0.0231(6) Uani 1 1 d . . . . .
C3 C 0.6153(4) 0.66776(17) 0.70966(15) 0.0236(6) Uani 1 1 d . . . . .
C4 C 0.4359(4) 0.61079(17) 0.73458(16) 0.0279(6) Uani 1 1 d . . . . .
H4 H 0.4290 0.5487 0.7152 0.033 Uiso 1 1 calc R U . . .
C5 C 0.2676(5) 0.64437(18) 0.78753(16) 0.0311(6) Uani 1 1 d . . . . .
H5 H 0.1461 0.6052 0.8044 0.037 Uiso 1 1 calc R U . . .
C6 C 0.2760(5) 0.73506(18) 0.81608(17) 0.0326(7) Uani 1 1 d . . . . .
H6 H 0.1604 0.7581 0.8523 0.039 Uiso 1 1 calc R U . . .
C7 C 0.4540(4) 0.79168(17) 0.79142(16) 0.0264(6) Uani 1 1 d . . . . .
H7 H 0.4601 0.8533 0.8120 0.032 Uiso 1 1 calc R U . . .
C8 C 1.1286(4) 0.86644(17) 0.62035(15) 0.0244(6) Uani 1 1 d . . . . .
H8 H 1.2190 0.8770 0.6728 0.029 Uiso 1 1 calc R U . . .
C9 C 1.0754(4) 0.96004(16) 0.58210(16) 0.0225(6) Uani 1 1 d . . . . .
C10 C 0.8808(4) 0.97830(18) 0.53507(17) 0.0294(6) Uani 1 1 d . . . . .
H10 H 0.7681 0.9317 0.5289 0.035 Uiso 1 1 calc R U . . .
C11 C 0.8496(5) 1.06364(19) 0.49716(17) 0.0343(7) Uani 1 1 d . . . . .
H11 H 0.7164 1.0751 0.4649 0.041 Uiso 1 1 calc R U . . .
C12 C 1.0118(5) 1.13217(18) 0.50620(17) 0.0339(7) Uani 1 1 d . . . . .
H12 H 0.9905 1.1907 0.4802 0.041 Uiso 1 1 calc R U . . .
C13 C 1.2048(5) 1.11525(17) 0.55318(16) 0.0333(7) Uani 1 1 d . . . . .
H13 H 1.3156 1.1625 0.5601 0.040 Uiso 1 1 calc R U . . .
C14 C 1.2377(5) 1.02974(16) 0.59029(16) 0.0272(6) Uani 1 1 d . . . . .
H14 H 1.3724 1.0184 0.6217 0.033 Uiso 1 1 calc R U . . .
C15 C 1.2724(5) 0.80864(17) 0.56067(16) 0.0303(7) Uani 1 1 d . . . . .
H15A H 1.3032 0.7483 0.5863 0.045 Uiso 1 1 calc R U . . .
H15B H 1.4166 0.8405 0.5497 0.045 Uiso 1 1 calc R U . . .
H15C H 1.1902 0.7999 0.5076 0.045 Uiso 1 1 calc R U . . .
C16 C 0.8151(5) 0.54030(16) 0.64451(18) 0.0352(7) Uani 1 1 d . . . . .
H16A H 0.8181 0.5087 0.6990 0.053 Uiso 1 1 calc R U . . .
H16B H 0.9585 0.5290 0.6147 0.053 Uiso 1 1 calc R U . . .
H16C H 0.6880 0.5167 0.6109 0.053 Uiso 1 1 calc R U . . .


_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
O1 C1 1.228(3) . ?
O2 C3 1.374(3) . ?
O2 C16 1.436(3) . ?
N1 C1 1.358(3) . ?
N1 C8 1.460(3) . ?
N1 H1 0.883(19) . ?
C1 C2 1.507(3) . ?
C2 C7 1.399(3) . ?
C2 C3 1.414(3) . ?
C3 C4 1.396(3) . ?
C4 C5 1.386(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.389(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.385(4) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 C9 1.516(3) . ?
C8 C15 1.521(3) . ?
C8 H8 1.0000 . ?
C9 C10 1.391(3) . ?
C9 C14 1.394(3) . ?
C10 C11 1.386(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.383(4) . ?
C11 H11 0.9500 . ?
C12 C13 1.379(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.384(3) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?

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
C3 O2 C16 118.7(2) . . ?
C1 N1 C8 122.2(2) . . ?
C1 N1 H1 115(2) . . ?
C8 N1 H1 117(2) . . ?
O1 C1 N1 122.2(2) . . ?
O1 C1 C2 121.0(2) . . ?
N1 C1 C2 116.8(2) . . ?
C7 C2 C3 117.7(2) . . ?
C7 C2 C1 116.0(2) . . ?
C3 C2 C1 126.2(2) . . ?
O2 C3 C4 122.6(2) . . ?
O2 C3 C2 117.0(2) . . ?
C4 C3 C2 120.3(2) . . ?
C5 C4 C3 120.3(2) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C4 C5 C6 120.3(3) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C7 C6 C5 119.5(3) . . ?
C7 C6 H6 120.2 . . ?
C5 C6 H6 120.2 . . ?
C6 C7 C2 121.9(3) . . ?
C6 C7 H7 119.1 . . ?
C2 C7 H7 119.1 . . ?
N1 C8 C9 114.0(2) . . ?
N1 C8 C15 108.0(2) . . ?
C9 C8 C15 110.8(2) . . ?
N1 C8 H8 107.9 . . ?
C9 C8 H8 107.9 . . ?
C15 C8 H8 107.9 . . ?
C10 C9 C14 118.4(2) . . ?
C10 C9 C8 123.6(2) . . ?
C14 C9 C8 117.9(2) . . ?
C11 C10 C9 120.8(3) . . ?
C11 C10 H10 119.6 . . ?
C9 C10 H10 119.6 . . ?
C12 C11 C10 120.1(3) . . ?
C12 C11 H11 119.9 . . ?
C10 C11 H11 119.9 . . ?
C13 C12 C11 119.7(3) . . ?
C13 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
C12 C13 C14 120.2(3) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
C13 C14 C9 120.8(3) . . ?
C13 C14 H14 119.6 . . ?
C9 C14 H14 119.6 . . ?
C8 C15 H15A 109.5 . . ?
C8 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C8 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O2 C16 H16A 109.5 . . ?
O2 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
O2 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 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
C8 N1 C1 O1 12.9(4) . . . . ?
C8 N1 C1 C2 -169.5(2) . . . . ?
O1 C1 C2 C7 16.6(3) . . . . ?
N1 C1 C2 C7 -161.0(2) . . . . ?
O1 C1 C2 C3 -163.9(2) . . . . ?
N1 C1 C2 C3 18.5(4) . . . . ?
C16 O2 C3 C4 -15.5(3) . . . . ?
C16 O2 C3 C2 165.3(2) . . . . ?
C7 C2 C3 O2 -178.8(2) . . . . ?
C1 C2 C3 O2 1.7(4) . . . . ?
C7 C2 C3 C4 2.0(4) . . . . ?
C1 C2 C3 C4 -177.5(2) . . . . ?
O2 C3 C4 C5 179.7(2) . . . . ?
C2 C3 C4 C5 -1.1(4) . . . . ?
C3 C4 C5 C6 0.1(4) . . . . ?
C4 C5 C6 C7 -0.2(4) . . . . ?
C5 C6 C7 C2 1.1(4) . . . . ?
C3 C2 C7 C6 -2.0(4) . . . . ?
C1 C2 C7 C6 177.5(2) . . . . ?
C1 N1 C8 C9 -76.9(3) . . . . ?
C1 N1 C8 C15 159.5(2) . . . . ?
N1 C8 C9 C10 -30.0(3) . . . . ?
C15 C8 C9 C10 92.2(3) . . . . ?
N1 C8 C9 C14 154.1(2) . . . . ?
C15 C8 C9 C14 -83.7(3) . . . . ?
C14 C9 C10 C11 0.2(4) . . . . ?
C8 C9 C10 C11 -175.7(2) . . . . ?
C9 C10 C11 C12 -0.4(4) . . . . ?
C10 C11 C12 C13 -0.1(4) . . . . ?
C11 C12 C13 C14 0.8(4) . . . . ?
C12 C13 C14 C9 -1.1(4) . . . . ?
C10 C9 C14 C13 0.6(4) . . . . ?
C8 C9 C14 C13 176.7(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O2 0.883(19) 1.94(2) 2.669(3) 139(3) .

_refine_diff_density_max         0.172
_refine_diff_density_min         -0.161
_refine_diff_density_rms         0.034


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: 1:1 hexanes:dichloromethane '
####################################################################### 
# 
# 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_16kaw108a
_database_code_depnum_ccdc_archive 'CCDC 1534594'
_audit_update_record             
;
2017-02-23 deposited with the CCDC.
2017-03-31 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
#_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H14 F3 N O, C15 H14 I N O'
_chemical_formula_sum            'C31 H28 F3 I N2 O2'
_chemical_formula_weight         644.45

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.3257 6.8362 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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'

_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.
;

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                   9.4943(2)
_cell_length_b                   16.1705(4)
_cell_length_c                   18.3454(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2816.52(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9858
_cell_measurement_theta_min      3.64
_cell_measurement_theta_max      68.25
_exptl_crystal_description       'transparent plate'
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.520
_exptl_crystal_F_000             1296
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.151
_exptl_crystal_size_mid          0.149
_exptl_crystal_size_min          0.096
_exptl_absorpt_coefficient_mu    9.367
_shelx_estimated_absorpt_T_min   0.332
_shelx_estimated_absorpt_T_max   0.467
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.532
_exptl_absorpt_correction_T_max  0.753
_exptl_absorpt_process_details   'SADABS-2014/7, Bruker AXS'
#_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.33
_diffrn_reflns_number            43195
_diffrn_reflns_av_unetI/netI     0.0489
_diffrn_reflns_av_R_equivalents  0.0765
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.644
_diffrn_reflns_theta_max         68.233
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5159
_reflns_number_gt                4723
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.764
_reflns_Friedel_fraction_max     0.996
_reflns_Friedel_fraction_full    0.996

_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.
;

_computing_data_collection       'APEX2 (Bruker, 2013)'
_computing_cell_refinement       APEX2
_computing_data_reduction        
;
SADABS (Bruker, 2013) and XPREP (Bruker, 2013)
;
_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'XSEED (Barbour, 2001)'
_computing_publication_material  'XSEED (Barbour, 2001)'

_refine_special_details          
;
All nonhydrogen atoms were located in a succesive difference Fourier electron
 density maps and refined using anisotropic diplacement parameters. All C-H
 hydrogen atoms were placed in calculated positions with Uiso = 1.2xUeqiv
 (1.5Ueq for methyl groups) of the connected C atoms. Those H atoms attached
 to nitrogen were located in Fourier diff maps and assigned Uiso = 1.2xUeqiv
 with N-H bond distances restrained to 0.85(2) angstroms.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0193P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1896 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.005(3)
_chemical_absolute_configuration rmad
_refine_ls_number_reflns         5159
_refine_ls_number_parameters     362
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0328
_refine_ls_R_factor_gt           0.0277
_refine_ls_wR_factor_ref         0.0612
_refine_ls_wR_factor_gt          0.0582
_refine_ls_goodness_of_fit_ref   1.004
_refine_ls_restrained_S_all      1.004
_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_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
I1 I 0.14444(3) 0.96083(2) 0.05983(2) 0.03302(10) Uani 1 1 d . . . . .
F1A F 0.6659(3) 0.98324(16) 0.36978(17) 0.0316(7) Uani 1 1 d . . . . .
F2A F 0.5544(3) 0.9244(2) 0.45816(19) 0.0404(8) Uani 1 1 d . . . . .
F3A F 0.7462(4) 0.9920(2) 0.47828(19) 0.0418(8) Uani 1 1 d . . . . .
O1 O 0.0357(3) 0.8403(2) 0.19825(19) 0.0256(8) Uani 1 1 d . . . . .
O1A O 0.5361(3) 0.8426(2) 0.30215(19) 0.0232(7) Uani 1 1 d . . . . .
N1 N 0.2331(4) 0.8504(3) 0.2669(2) 0.0191(9) Uani 1 1 d . . . . .
H1 H 0.304(5) 0.854(3) 0.269(3) 0.005(13) Uiso 1 1 d . . . . .
N1A N 0.7326(4) 0.8525(2) 0.2317(2) 0.0174(8) Uani 1 1 d . . . . .
H1A H 0.817(5) 0.851(3) 0.231(2) 0.006(12) Uiso 1 1 d . . . . .
C1 C 0.1641(5) 0.8349(3) 0.2049(3) 0.0201(10) Uani 1 1 d . . . . .
C2 C 0.2553(5) 0.8079(3) 0.1419(3) 0.0178(9) Uani 1 1 d . . . . .
C3 C 0.3366(5) 0.7361(3) 0.1476(3) 0.0225(10) Uani 1 1 d . . . . .
H3 H 0.3352 0.7051 0.1916 0.027 Uiso 1 1 calc R U . . .
C4 C 0.4190(5) 0.7094(3) 0.0898(3) 0.0283(12) Uani 1 1 d . . . . .
H4 H 0.4701 0.6591 0.0938 0.034 Uiso 1 1 calc R U . . .
C5 C 0.4276(6) 0.7552(3) 0.0266(3) 0.0304(12) Uani 1 1 d . . . . .
H5 H 0.4867 0.7375 -0.0122 0.037 Uiso 1 1 calc R U . . .
C6 C 0.3497(6) 0.8271(3) 0.0200(3) 0.0285(10) Uani 1 1 d . . . . .
H6 H 0.3562 0.8593 -0.0231 0.034 Uiso 1 1 calc R U . . .
C7 C 0.2615(5) 0.8522(3) 0.0767(3) 0.0225(11) Uani 1 1 d . . . . .
C8 C 0.1612(5) 0.8827(3) 0.3315(2) 0.0192(9) Uani 1 1 d . . . . .
H8 H 0.0645 0.8583 0.3327 0.023 Uiso 1 1 calc R U . . .
C9 C 0.1459(5) 0.9764(2) 0.3278(2) 0.0191(9) Uani 1 1 d . . . . .
C10 C 0.0122(5) 1.0120(3) 0.3347(3) 0.0241(11) Uani 1 1 d . . . . .
H10 H -0.0678 0.9772 0.3400 0.029 Uiso 1 1 calc R U . . .
C11 C -0.0053(5) 1.0967(3) 0.3341(3) 0.0277(12) Uani 1 1 d . . . . .
H11 H -0.0969 1.1198 0.3389 0.033 Uiso 1 1 calc R U . . .
C12 C 0.1103(5) 1.1479(3) 0.3265(3) 0.0279(12) Uani 1 1 d . . . . .
H12 H 0.0988 1.2063 0.3267 0.033 Uiso 1 1 calc R U . . .
C13 C 0.2434(5) 1.1136(3) 0.3187(3) 0.0276(12) Uani 1 1 d . . . . .
H13 H 0.3229 1.1486 0.3126 0.033 Uiso 1 1 calc R U . . .
C14 C 0.2607(5) 1.0281(3) 0.3197(3) 0.0263(11) Uani 1 1 d . . . . .
H14 H 0.3523 1.0051 0.3149 0.032 Uiso 1 1 calc R U . . .
C15 C 0.2382(5) 0.8548(3) 0.4002(3) 0.0241(10) Uani 1 1 d . . . . .
H15A H 0.2344 0.7944 0.4038 0.036 Uiso 1 1 calc R U . . .
H15B H 0.1931 0.8793 0.4430 0.036 Uiso 1 1 calc R U . . .
H15C H 0.3367 0.8727 0.3978 0.036 Uiso 1 1 calc R U . . .
C1A C 0.6658(5) 0.8383(3) 0.2944(2) 0.0171(9) Uani 1 1 d . . . . .
C2A C 0.7589(5) 0.8139(3) 0.3574(3) 0.0192(10) Uani 1 1 d . . . . .
C3A C 0.8368(5) 0.7412(3) 0.3541(3) 0.0210(10) Uani 1 1 d . . . . .
H3A H 0.8330 0.7082 0.3113 0.025 Uiso 1 1 calc R U . . .
C4A C 0.9194(5) 0.7163(3) 0.4117(3) 0.0277(12) Uani 1 1 d . . . . .
H4A H 0.9705 0.6659 0.4083 0.033 Uiso 1 1 calc R U . . .
C5A C 0.9293(6) 0.7634(3) 0.4743(3) 0.0298(12) Uani 1 1 d . . . . .
H5A H 0.9869 0.7459 0.5138 0.036 Uiso 1 1 calc R U . . .
C6A C 0.8532(6) 0.8370(3) 0.4788(3) 0.0279(10) Uani 1 1 d . . . . .
H6A H 0.8600 0.8703 0.5213 0.033 Uiso 1 1 calc R U . . .
C7A C 0.7674(5) 0.8620(3) 0.4214(2) 0.0198(10) Uani 1 1 d . . . . .
C8A C 0.6574(5) 0.8823(3) 0.1669(2) 0.0178(9) Uani 1 1 d . . . . .
H8A H 0.5615 0.8567 0.1667 0.021 Uiso 1 1 calc R U . . .
C9A C 0.6396(5) 0.9762(2) 0.1686(2) 0.0179(9) Uani 1 1 d . . . . .
C10A C 0.5074(5) 1.0102(3) 0.1592(3) 0.0232(11) Uani 1 1 d . . . . .
H10A H 0.4284 0.9749 0.1527 0.028 Uiso 1 1 calc R U . . .
C11A C 0.4888(6) 1.0953(3) 0.1593(3) 0.0286(12) Uani 1 1 d . . . . .
H11A H 0.3976 1.1181 0.1521 0.034 Uiso 1 1 calc R U . . .
C12A C 0.6031(5) 1.1470(3) 0.1700(3) 0.0260(11) Uani 1 1 d . . . . .
H12A H 0.5905 1.2053 0.1714 0.031 Uiso 1 1 calc R U . . .
C13A C 0.7358(6) 1.1133(3) 0.1786(3) 0.0271(11) Uani 1 1 d . . . . .
H13A H 0.8149 1.1486 0.1845 0.033 Uiso 1 1 calc R U . . .
C14A C 0.7543(5) 1.0287(3) 0.1785(3) 0.0226(10) Uani 1 1 d . . . . .
H14A H 0.8457 1.0061 0.1853 0.027 Uiso 1 1 calc R U . . .
C15A C 0.7351(5) 0.8536(3) 0.0981(3) 0.0215(10) Uani 1 1 d . . . . .
H15D H 0.8304 0.8769 0.0977 0.032 Uiso 1 1 calc R U . . .
H15E H 0.6838 0.8725 0.0549 0.032 Uiso 1 1 calc R U . . .
H15F H 0.7407 0.7931 0.0978 0.032 Uiso 1 1 calc R U . . .
C16A C 0.6846(5) 0.9405(3) 0.4311(3) 0.0285(12) 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
I1 C7 2.102(5) . ?
F1A C16A 1.333(6) . ?
F2A C16A 1.357(6) . ?
F3A C16A 1.336(6) . ?
O1 C1 1.228(6) . ?
O1A C1A 1.241(6) . ?
N1 C1 1.337(6) . ?
N1 C8 1.463(6) . ?
N1 H1 0.68(5) . ?
N1A C1A 1.334(6) . ?
N1A C8A 1.467(6) . ?
N1A H1A 0.80(5) . ?
C1 C2 1.509(6) . ?
C2 C7 1.395(7) . ?
C2 C3 1.398(6) . ?
C3 C4 1.387(7) . ?
C3 H3 0.9500 . ?
C4 C5 1.379(8) . ?
C4 H4 0.9500 . ?
C5 C6 1.382(8) . ?
C5 H5 0.9500 . ?
C6 C7 1.396(7) . ?
C6 H6 0.9500 . ?
C8 C9 1.523(6) . ?
C8 C15 1.525(6) . ?
C8 H8 1.0000 . ?
C9 C14 1.382(7) . ?
C9 C10 1.399(7) . ?
C10 C11 1.380(7) . ?
C10 H10 0.9500 . ?
C11 C12 1.383(7) . ?
C11 H11 0.9500 . ?
C12 C13 1.387(8) . ?
C12 H12 0.9500 . ?
C13 C14 1.393(8) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C1A C2A 1.508(6) . ?
C2A C3A 1.391(6) . ?
C2A C7A 1.410(6) . ?
C3A C4A 1.377(7) . ?
C3A H3A 0.9500 . ?
C4A C5A 1.382(8) . ?
C4A H4A 0.9500 . ?
C5A C6A 1.395(7) . ?
C5A H5A 0.9500 . ?
C6A C7A 1.391(7) . ?
C6A H6A 0.9500 . ?
C7A C16A 1.503(7) . ?
C8A C9A 1.528(5) . ?
C8A C15A 1.534(6) . ?
C8A H8A 1.0000 . ?
C9A C10A 1.381(7) . ?
C9A C14A 1.392(7) . ?
C10A C11A 1.388(7) . ?
C10A H10A 0.9500 . ?
C11A C12A 1.384(7) . ?
C11A H11A 0.9500 . ?
C12A C13A 1.382(7) . ?
C12A H12A 0.9500 . ?
C13A C14A 1.380(7) . ?
C13A H13A 0.9500 . ?
C14A H14A 0.9500 . ?
C15A H15D 0.9800 . ?
C15A H15E 0.9800 . ?
C15A H15F 0.9800 . ?

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
C1 N1 C8 121.8(4) . . ?
C1 N1 H1 123(4) . . ?
C8 N1 H1 113(4) . . ?
C1A N1A C8A 121.6(4) . . ?
C1A N1A H1A 118(3) . . ?
C8A N1A H1A 119(3) . . ?
O1 C1 N1 123.9(5) . . ?
O1 C1 C2 120.9(4) . . ?
N1 C1 C2 115.1(4) . . ?
C7 C2 C3 117.8(4) . . ?
C7 C2 C1 122.2(4) . . ?
C3 C2 C1 120.0(4) . . ?
C4 C3 C2 120.9(5) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C5 C4 C3 120.6(5) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
C4 C5 C6 119.6(5) . . ?
C4 C5 H5 120.2 . . ?
C6 C5 H5 120.2 . . ?
C5 C6 C7 120.0(5) . . ?
C5 C6 H6 120.0 . . ?
C7 C6 H6 120.0 . . ?
C2 C7 C6 121.0(4) . . ?
C2 C7 I1 122.2(4) . . ?
C6 C7 I1 116.8(4) . . ?
N1 C8 C9 111.3(4) . . ?
N1 C8 C15 109.8(4) . . ?
C9 C8 C15 112.2(4) . . ?
N1 C8 H8 107.8 . . ?
C9 C8 H8 107.8 . . ?
C15 C8 H8 107.8 . . ?
C14 C9 C10 118.4(4) . . ?
C14 C9 C8 122.1(4) . . ?
C10 C9 C8 119.4(4) . . ?
C11 C10 C9 121.2(5) . . ?
C11 C10 H10 119.4 . . ?
C9 C10 H10 119.4 . . ?
C10 C11 C12 120.0(5) . . ?
C10 C11 H11 120.0 . . ?
C12 C11 H11 120.0 . . ?
C11 C12 C13 119.6(4) . . ?
C11 C12 H12 120.2 . . ?
C13 C12 H12 120.2 . . ?
C12 C13 C14 120.2(5) . . ?
C12 C13 H13 119.9 . . ?
C14 C13 H13 119.9 . . ?
C9 C14 C13 120.6(5) . . ?
C9 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C8 C15 H15A 109.5 . . ?
C8 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C8 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
O1A C1A N1A 124.1(4) . . ?
O1A C1A C2A 120.5(4) . . ?
N1A C1A C2A 115.3(4) . . ?
C3A C2A C7A 118.2(4) . . ?
C3A C2A C1A 119.9(4) . . ?
C7A C2A C1A 121.8(4) . . ?
C4A C3A C2A 121.1(4) . . ?
C4A C3A H3A 119.5 . . ?
C2A C3A H3A 119.5 . . ?
C3A C4A C5A 121.1(5) . . ?
C3A C4A H4A 119.5 . . ?
C5A C4A H4A 119.5 . . ?
C4A C5A C6A 119.0(5) . . ?
C4A C5A H5A 120.5 . . ?
C6A C5A H5A 120.5 . . ?
C7A C6A C5A 120.4(4) . . ?
C7A C6A H6A 119.8 . . ?
C5A C6A H6A 119.8 . . ?
C6A C7A C2A 120.2(4) . . ?
C6A C7A C16A 117.5(4) . . ?
C2A C7A C16A 122.3(4) . . ?
N1A C8A C9A 111.4(4) . . ?
N1A C8A C15A 109.5(4) . . ?
C9A C8A C15A 111.7(4) . . ?
N1A C8A H8A 108.0 . . ?
C9A C8A H8A 108.0 . . ?
C15A C8A H8A 108.0 . . ?
C10A C9A C14A 119.0(4) . . ?
C10A C9A C8A 119.6(4) . . ?
C14A C9A C8A 121.5(4) . . ?
C9A C10A C11A 120.7(5) . . ?
C9A C10A H10A 119.7 . . ?
C11A C10A H10A 119.7 . . ?
C12A C11A C10A 119.9(5) . . ?
C12A C11A H11A 120.0 . . ?
C10A C11A H11A 120.0 . . ?
C13A C12A C11A 119.5(4) . . ?
C13A C12A H12A 120.2 . . ?
C11A C12A H12A 120.2 . . ?
C14A C13A C12A 120.5(5) . . ?
C14A C13A H13A 119.8 . . ?
C12A C13A H13A 119.8 . . ?
C13A C14A C9A 120.4(5) . . ?
C13A C14A H14A 119.8 . . ?
C9A C14A H14A 119.8 . . ?
C8A C15A H15D 109.5 . . ?
C8A C15A H15E 109.5 . . ?
H15D C15A H15E 109.5 . . ?
C8A C15A H15F 109.5 . . ?
H15D C15A H15F 109.5 . . ?
H15E C15A H15F 109.5 . . ?
F1A C16A F3A 106.3(4) . . ?
F1A C16A F2A 106.7(4) . . ?
F3A C16A F2A 106.3(4) . . ?
F1A C16A C7A 114.1(4) . . ?
F3A C16A C7A 112.0(4) . . ?
F2A C16A C7A 111.0(4) . . ?

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
C8 N1 C1 O1 -5.5(7) . . . . ?
C8 N1 C1 C2 175.6(4) . . . . ?
O1 C1 C2 C7 60.9(6) . . . . ?
N1 C1 C2 C7 -120.2(5) . . . . ?
O1 C1 C2 C3 -118.7(5) . . . . ?
N1 C1 C2 C3 60.1(6) . . . . ?
C7 C2 C3 C4 -0.9(7) . . . . ?
C1 C2 C3 C4 178.8(4) . . . . ?
C2 C3 C4 C5 3.0(7) . . . . ?
C3 C4 C5 C6 -2.0(8) . . . . ?
C4 C5 C6 C7 -0.9(8) . . . . ?
C3 C2 C7 C6 -2.1(7) . . . . ?
C1 C2 C7 C6 178.3(4) . . . . ?
C3 C2 C7 I1 179.6(3) . . . . ?
C1 C2 C7 I1 -0.1(6) . . . . ?
C5 C6 C7 C2 3.0(7) . . . . ?
C5 C6 C7 I1 -178.6(4) . . . . ?
C1 N1 C8 C9 -83.5(5) . . . . ?
C1 N1 C8 C15 151.7(4) . . . . ?
N1 C8 C9 C14 -56.9(6) . . . . ?
C15 C8 C9 C14 66.6(6) . . . . ?
N1 C8 C9 C10 125.0(5) . . . . ?
C15 C8 C9 C10 -111.5(5) . . . . ?
C14 C9 C10 C11 -0.4(8) . . . . ?
C8 C9 C10 C11 177.8(5) . . . . ?
C9 C10 C11 C12 0.0(9) . . . . ?
C10 C11 C12 C13 0.7(8) . . . . ?
C11 C12 C13 C14 -1.1(8) . . . . ?
C10 C9 C14 C13 0.0(7) . . . . ?
C8 C9 C14 C13 -178.1(5) . . . . ?
C12 C13 C14 C9 0.7(8) . . . . ?
C8A N1A C1A O1A 5.8(7) . . . . ?
C8A N1A C1A C2A -175.7(4) . . . . ?
O1A C1A C2A C3A 116.0(5) . . . . ?
N1A C1A C2A C3A -62.6(6) . . . . ?
O1A C1A C2A C7A -62.5(6) . . . . ?
N1A C1A C2A C7A 118.9(5) . . . . ?
C7A C2A C3A C4A 0.4(7) . . . . ?
C1A C2A C3A C4A -178.1(4) . . . . ?
C2A C3A C4A C5A -1.0(7) . . . . ?
C3A C4A C5A C6A 0.4(8) . . . . ?
C4A C5A C6A C7A 0.8(8) . . . . ?
C5A C6A C7A C2A -1.4(7) . . . . ?
C5A C6A C7A C16A 177.9(5) . . . . ?
C3A C2A C7A C6A 0.7(7) . . . . ?
C1A C2A C7A C6A 179.3(4) . . . . ?
C3A C2A C7A C16A -178.5(4) . . . . ?
C1A C2A C7A C16A 0.0(7) . . . . ?
C1A N1A C8A C9A 83.5(5) . . . . ?
C1A N1A C8A C15A -152.5(4) . . . . ?
N1A C8A C9A C10A -127.5(4) . . . . ?
C15A C8A C9A C10A 109.7(5) . . . . ?
N1A C8A C9A C14A 53.1(5) . . . . ?
C15A C8A C9A C14A -69.6(5) . . . . ?
C14A C9A C10A C11A 0.4(7) . . . . ?
C8A C9A C10A C11A -179.0(5) . . . . ?
C9A C10A C11A C12A -1.0(8) . . . . ?
C10A C11A C12A C13A 1.7(8) . . . . ?
C11A C12A C13A C14A -1.8(8) . . . . ?
C12A C13A C14A C9A 1.2(8) . . . . ?
C10A C9A C14A C13A -0.4(7) . . . . ?
C8A C9A C14A C13A 178.9(4) . . . . ?
C6A C7A C16A F1A 147.0(4) . . . . ?
C2A C7A C16A F1A -33.7(6) . . . . ?
C6A C7A C16A F3A 26.2(6) . . . . ?
C2A C7A C16A F3A -154.6(4) . . . . ?
C6A C7A C16A F2A -92.5(5) . . . . ?
C2A C7A C16A F2A 86.8(6) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O1A 0.68(5) 2.29(5) 2.951(5) 165(5) .
N1A H1A O1 0.80(5) 2.17(5) 2.949(5) 164(4) 1_655

_refine_diff_density_max         0.624
_refine_diff_density_min         -0.507
_refine_diff_density_rms         0.069


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: 1:1 hexanes:dichloromethane '
####################################################################### 
# 
# 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_16kaw58
_database_code_depnum_ccdc_archive 'CCDC 1534590'
_audit_update_record             
;
2017-02-23 deposited with the CCDC.
2017-03-31 downloaded from the CCDC.
;


_audit_creation_method           SHELXL-2014/7
#_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H14 F N O, C15 H15 N O'
_chemical_formula_sum            'C30 H29 F N2 O2'
_chemical_formula_weight         468.55

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           1
_space_group_name_H-M_alt        'P 1'
_space_group_name_Hall           'P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'

_cell_length_a                   5.3540(2)
_cell_length_b                   8.3824(4)
_cell_length_c                   13.8585(7)
_cell_angle_alpha                96.477(3)
_cell_angle_beta                 93.829(3)
_cell_angle_gamma                105.841(3)
_cell_volume                     591.42(5)
_cell_formula_units_Z            1
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    2680
_cell_measurement_theta_min      3.23
_cell_measurement_theta_max      68.11
_exptl_crystal_description       'transparent plate'
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.316
_exptl_crystal_F_000             248
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.392
_exptl_crystal_size_mid          0.066
_exptl_crystal_size_min          0.066
_exptl_absorpt_coefficient_mu    0.705
_shelx_estimated_absorpt_T_min   0.770
_shelx_estimated_absorpt_T_max   0.955
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.653
_exptl_absorpt_correction_T_max  0.753
_exptl_absorpt_process_details   'SADABS-2014/7, Bruker AXS'
#_exptl_absorpt_special_details   ?


_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.33
_diffrn_standards_number         ?
_diffrn_standards_interval_count .
_diffrn_standards_interval_time  .
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            13271
_diffrn_reflns_av_unetI/netI     0.0700
_diffrn_reflns_av_R_equivalents  0.0760
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.226
_diffrn_reflns_theta_max         68.246
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.979
_diffrn_measured_fraction_theta_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.871
#_diffrn_reflns_point_group_measured_fraction_full 0.872
_reflns_number_total             3785
_reflns_number_gt                2730
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.779
_reflns_Friedel_fraction_max     0.762
_reflns_Friedel_fraction_full    0.765

_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.
;




_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1132P)²+0.0085P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 919 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.1(4)
_chemical_absolute_configuration rm
_refine_ls_number_reflns         3785
_refine_ls_number_parameters     406
_refine_ls_number_restraints     41
_refine_ls_R_factor_all          0.0946
_refine_ls_R_factor_gt           0.0668
#_refine_ls_wR_factor_ref         0.1886_computing_data_collection
_computing_cell_refinement       APEX2
_computing_data_reduction        
;
SADABS (Bruker, 2013) and XPREP (Bruker, 2013)
;
_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'XSEED (Barbour, 2001)'
_computing_publication_material  'XSEED (Barbour, 2001)'

_refine_special_details          
;All nonhydrogen atoms were located in a succesive difference Fourier electron
 density maps and refined using anisotropic diplacement parameters. All C-H
 hydrogen atoms were placed in calculated positions with Uiso = 1.2xUeqiv
 (1.5Ueq for methyl groups) of the connected C atoms. Those H atoms attached
 to nitrogen were located in Fourier diff maps and assigned Uiso = 1.2xUeqiv
 with N-H bond distances restrained to 0.85(2) angstroms.

The 2-fluoro substituted aryl ring modeled with 1:1 two-part disorder as
 determined from refinement of the ocupancy factors.  Aryl ring C3B
 was restrained with the rigid body refinement RIGU command., Disorder
;
_refine_ls_wR_factor_gt          0.1661
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.002
_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_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 1.3742(14) 1.0469(9) 0.7516(6) 0.0489(18) Uani 0.5 1 d . . P A 1
F3 F 1.2276(14) 0.7437(10) 0.6812(6) 0.054(2) Uani 0.5 1 d . . P B 2
O1A O 0.9685(8) 0.5195(5) 0.3880(3) 0.0338(12) Uani 1 1 d . . . . .
N1A N 0.5413(9) 0.5039(6) 0.3640(4) 0.0291(13) Uani 1 1 d D . . . .
H1A H 0.392(6) 0.496(8) 0.386(4) 0.035 Uiso 1 1 d D U . . .
C1A C 0.7494(10) 0.4987(7) 0.4158(4) 0.0220(14) Uani 1 1 d . . . . .
C2A C 0.7127(10) 0.4562(7) 0.5185(5) 0.0260(15) Uani 1 1 d . . . . .
C3A C 0.938(3) 0.5136(15) 0.5870(11) 0.036(3) Uani 0.5 1 d . . P C 1
H3A H 1.1029 0.5670 0.5669 0.043 Uiso 0.5 1 calc R U P C 1
C4A C 0.914(2) 0.4915(16) 0.6796(11) 0.035(3) Uani 0.5 1 d . . P C 1
H4A H 1.0617 0.5406 0.7262 0.041 Uiso 0.5 1 calc R U P C 1
C5A C 0.6748(11) 0.3960(8) 0.7135(5) 0.0295(16) Uani 1 1 d . . . . .
H5A H 0.6665 0.3728 0.7790 0.035 Uiso 1 1 calc R U . C 1
C6A C 0.450(2) 0.3385(13) 0.6415(8) 0.019(2) Uani 0.5 1 d . . P C 1
H6A H 0.2874 0.2757 0.6595 0.023 Uiso 0.5 1 calc R U P C 1
C7A C 0.468(2) 0.3741(15) 0.5465(10) 0.028(3) Uani 0.5 1 d . . P C 1
H7A H 0.3174 0.3432 0.5008 0.034 Uiso 0.5 1 calc R U P C 1
C8A C 0.5583(12) 0.5546(7) 0.2634(5) 0.0285(15) Uani 1 1 d . . . . .
H8A H 0.7067 0.5209 0.2355 0.034 Uiso 1 1 calc R U . . .
C9A C 0.6204(11) 0.7479(7) 0.2689(5) 0.0282(16) Uani 1 1 d . . . . .
C10A C 0.4618(11) 0.8308(8) 0.3119(5) 0.0268(15) Uani 1 1 d . . . . .
H10A H 0.3121 0.7701 0.3390 0.032 Uiso 1 1 calc R U . . .
C11A C 0.5185(12) 1.0053(7) 0.3166(5) 0.0305(17) Uani 1 1 d . . . . .
H11A H 0.4142 1.0644 0.3497 0.037 Uiso 1 1 calc R U . . .
C12A C 0.7320(12) 1.0905(7) 0.2714(5) 0.0306(15) Uani 1 1 d . . . . .
H12A H 0.7687 1.2081 0.2722 0.037 Uiso 1 1 calc R U . . .
C13A C 0.8898(11) 1.0073(7) 0.2257(5) 0.0304(16) Uani 1 1 d . . . . .
H13A H 1.0343 1.0662 0.1953 0.036 Uiso 1 1 calc R U . . .
C14A C 0.8311(13) 0.8309(7) 0.2251(5) 0.0322(17) Uani 1 1 d . . . . .
H14A H 0.9378 0.7708 0.1945 0.039 Uiso 1 1 calc R U . . .
C15A C 0.3097(11) 0.4607(8) 0.1976(5) 0.0348(17) Uani 1 1 d . . . . .
H15A H 0.1584 0.4818 0.2270 0.052 Uiso 1 1 calc R U . . .
H15B H 0.2926 0.3404 0.1900 0.052 Uiso 1 1 calc R U . . .
H15C H 0.3186 0.4994 0.1334 0.052 Uiso 1 1 calc R U . . .
O1B O 0.6817(8) 0.8349(6) 0.8493(4) 0.0379(13) Uani 1 1 d . . . . .
N1B N 1.1106(9) 0.8460(6) 0.8727(4) 0.0270(13) Uani 1 1 d D . . . .
H1B H 1.258(6) 0.854(8) 0.848(4) 0.032 Uiso 1 1 d D U . . .
C1B C 0.8965(11) 0.8603(8) 0.8162(5) 0.0336(17) Uani 1 1 d . . . . .
C2B C 0.9327(11) 0.8994(7) 0.7156(5) 0.0282(15) Uani 1 1 d . U . . .
C3B C 0.7160(19) 0.8399(13) 0.6513(8) 0.018(2) Uani 0.5 1 d . U P D 1
H3B H 0.5573 0.7770 0.6718 0.021 Uiso 0.5 1 calc R U P D 1
C4B C 0.727(2) 0.8722(14) 0.5526(9) 0.025(2) Uani 0.5 1 d . U P D 1
H4B H 0.5753 0.8333 0.5074 0.030 Uiso 0.5 1 calc R U P D 1
C5B C 0.9579(12) 0.9594(8) 0.5235(5) 0.0337(16) Uani 1 1 d . U . . .
H5B H 0.9695 0.9826 0.4581 0.040 Uiso 1 1 calc R U . D 1
C6B C 1.174(3) 1.0131(19) 0.5915(10) 0.042(4) Uani 0.5 1 d . U P A 1
H6B H 1.3380 1.0692 0.5720 0.050 Uiso 0.5 1 calc R U P A 1
C7B C 1.155(2) 0.9865(14) 0.6872(10) 0.025(2) Uani 0.5 1 d . U P A 1
C8B C 1.0888(10) 0.7941(7) 0.9680(5) 0.0273(16) Uani 1 1 d . . . . .
H8B H 0.9419 0.8292 0.9963 0.033 Uiso 1 1 calc R U . . .
C9B C 1.0313(10) 0.6093(7) 0.9654(4) 0.0264(15) Uani 1 1 d . . . . .
C10B C 1.1838(11) 0.5146(7) 0.9181(5) 0.0304(17) Uani 1 1 d . . . . .
H10B H 1.3293 0.5697 0.8868 0.036 Uiso 1 1 calc R U . . .
C11B C 1.1220(12) 0.3443(8) 0.9176(5) 0.0356(17) Uani 1 1 d . . . . .
H11B H 1.2273 0.2843 0.8859 0.043 Uiso 1 1 calc R U . . .
C12B C 0.9138(13) 0.2579(8) 0.9611(6) 0.041(2) Uani 1 1 d . . . . .
H12B H 0.8737 0.1401 0.9602 0.049 Uiso 1 1 calc R U . . .
C13B C 0.7644(13) 0.3495(8) 1.0065(5) 0.0375(19) Uani 1 1 d . . . . .
H13B H 0.6204 0.2925 1.0379 0.045 Uiso 1 1 calc R U . . .
C14B C 0.8157(10) 0.5175(8) 1.0078(5) 0.0295(17) Uani 1 1 d . . . . .
H14B H 0.7039 0.5742 1.0379 0.035 Uiso 1 1 calc R U . . .
C15B C 1.3397(12) 0.8846(7) 1.0339(5) 0.0292(16) Uani 1 1 d . . . . .
H15D H 1.4863 0.8506 1.0082 0.044 Uiso 1 1 calc R U . . .
H15E H 1.3213 0.8555 1.1001 0.044 Uiso 1 1 calc R U . . .
H15F H 1.3724 1.0058 1.0355 0.044 Uiso 1 1 calc R U . . .
C3C C 0.864(2) 0.3576(17) 0.5621(9) 0.029(3) Uani 0.5 1 d . . P C 2
H3C H 0.9791 0.3137 0.5249 0.034 Uiso 0.5 1 calc R U P C 2
C4C C 0.841(3) 0.3285(14) 0.6563(10) 0.035(4) Uani 0.5 1 d . . P C 2
H4C H 0.9379 0.2622 0.6839 0.042 Uiso 0.5 1 calc R U P C 2
C6C C 0.535(2) 0.4898(16) 0.6739(12) 0.038(4) Uani 0.5 1 d . . P C 2
H6C H 0.4299 0.5393 0.7134 0.045 Uiso 0.5 1 calc R U P C 2
C7C C 0.541(2) 0.5135(14) 0.5807(9) 0.026(3) Uani 0.5 1 d . . P C 2
H7C H 0.4284 0.5708 0.5541 0.031 Uiso 0.5 1 calc R U P C 2
C3D C 0.793(2) 0.9957(14) 0.6732(11) 0.032(3) Uani 0.5 1 d . . P D 2
H3D H 0.6841 1.0419 0.7124 0.038 Uiso 0.5 1 calc R U P D 2
C4D C 0.801(2) 1.0292(17) 0.5766(10) 0.034(3) Uani 0.5 1 d . . P D 2
H4D H 0.7043 1.0962 0.5501 0.041 Uiso 0.5 1 calc R U P D 2
C6D C 1.114(2) 0.8737(13) 0.5574(8) 0.024(3) Uani 0.5 1 d . . P B 2
H6D H 1.2304 0.8358 0.5180 0.028 Uiso 0.5 1 calc R U P B 2
C7D C 1.095(2) 0.8427(14) 0.6556(11) 0.034(3) Uani 0.5 1 d . . P B 2


_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 C7B 1.366(13) . ?
F3 C7D 1.292(14) . ?
O1A C1A 1.233(7) . ?
N1A C1A 1.299(8) . ?
N1A C8A 1.503(8) . ?
N1A H1A 0.86(3) . ?
C1A C2A 1.518(9) . ?
C2A C7A 1.404(13) . ?
C2A C3A 1.420(14) . ?
C2A C7C 1.437(13) . ?
C2A C3C 1.455(15) . ?
C3A C4A 1.33(2) . ?
C3A H3A 0.9500 . ?
C4A C5A 1.453(14) . ?
C4A H4A 0.9500 . ?
C5A C6C 1.360(15) . ?
C5A C4C 1.419(16) . ?
C5A C6A 1.448(12) . ?
C5A H5A 0.9500 . ?
C6A C7A 1.387(17) . ?
C6A H6A 0.9500 . ?
C7A H7A 0.9500 . ?
C8A C15A 1.525(8) . ?
C8A C9A 1.554(8) . ?
C8A H8A 1.0000 . ?
C9A C10A 1.362(9) . ?
C9A C14A 1.372(9) . ?
C10A C11A 1.404(8) . ?
C10A H10A 0.9500 . ?
C11A C12A 1.400(9) . ?
C11A H11A 0.9500 . ?
C12A C13A 1.376(9) . ?
C12A H12A 0.9500 . ?
C13A C14A 1.425(8) . ?
C13A H13A 0.9500 . ?
C14A H14A 0.9500 . ?
C15A H15A 0.9800 . ?
C15A H15B 0.9800 . ?
C15A H15C 0.9800 . ?
O1B C1B 1.240(8) . ?
N1B C1B 1.385(8) . ?
N1B C8B 1.438(8) . ?
N1B H1B 0.87(3) . ?
C1B C2B 1.480(10) . ?
C2B C7B 1.325(13) . ?
C2B C3B 1.355(12) . ?
C2B C7D 1.382(15) . ?
C2B C3D 1.392(14) . ?
C3B C4B 1.426(16) . ?
C3B H3B 0.9500 . ?
C4B C5B 1.364(14) . ?
C4B H4B 0.9500 . ?
C5B C6D 1.336(14) . ?
C5B C4D 1.356(15) . ?
C5B C6B 1.379(15) . ?
C5B H5B 0.9500 . ?
C6B C7B 1.375(19) . ?
C6B H6B 0.9500 . ?
C8B C9B 1.490(8) . ?
C8B C15B 1.529(8) . ?
C8B H8B 1.0000 . ?
C9B C14B 1.406(8) . ?
C9B C10B 1.427(9) . ?
C10B C11B 1.373(9) . ?
C10B H10B 0.9500 . ?
C11B C12B 1.371(10) . ?
C11B H11B 0.9500 . ?
C12B C13B 1.385(11) . ?
C12B H12B 0.9500 . ?
C13B C14B 1.357(9) . ?
C13B H13B 0.9500 . ?
C14B H14B 0.9500 . ?
C15B H15D 0.9800 . ?
C15B H15E 0.9800 . ?
C15B H15F 0.9800 . ?
C3C C4C 1.362(18) . ?
C3C H3C 0.9500 . ?
C4C H4C 0.9500 . ?
C6C C7C 1.33(2) . ?
C6C H6C 0.9500 . ?
C7C H7C 0.9500 . ?
C3D C4D 1.40(2) . ?
C3D H3D 0.9500 . ?
C4D H4D 0.9500 . ?
C6D C7D 1.420(18) . ?
C6D H6D 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1A N1A C8A 120.4(5) . . ?
C1A N1A H1A 124(4) . . ?
C8A N1A H1A 114(4) . . ?
O1A C1A N1A 125.9(6) . . ?
O1A C1A C2A 118.0(5) . . ?
N1A C1A C2A 116.0(5) . . ?
C7A C2A C3A 121.4(9) . . ?
C7C C2A C3C 115.4(8) . . ?
C7A C2A C1A 122.5(7) . . ?
C3A C2A C1A 116.0(8) . . ?
C7C C2A C1A 124.2(7) . . ?
C3C C2A C1A 120.4(7) . . ?
C4A C3A C2A 118.8(12) . . ?
C4A C3A H3A 120.6 . . ?
C2A C3A H3A 120.6 . . ?
C3A C4A C5A 123.4(11) . . ?
C3A C4A H4A 118.3 . . ?
C5A C4A H4A 118.3 . . ?
C6C C5A C4C 119.7(10) . . ?
C6A C5A C4A 115.9(8) . . ?
C6A C5A H5A 122.1 . . ?
C4A C5A H5A 122.1 . . ?
C7A C6A C5A 120.6(9) . . ?
C7A C6A H6A 119.7 . . ?
C5A C6A H6A 119.7 . . ?
C6A C7A C2A 119.4(10) . . ?
C6A C7A H7A 120.3 . . ?
C2A C7A H7A 120.3 . . ?
N1A C8A C15A 110.2(5) . . ?
N1A C8A C9A 110.4(5) . . ?
C15A C8A C9A 113.0(5) . . ?
N1A C8A H8A 107.7 . . ?
C15A C8A H8A 107.7 . . ?
C9A C8A H8A 107.7 . . ?
C10A C9A C14A 121.2(6) . . ?
C10A C9A C8A 120.6(5) . . ?
C14A C9A C8A 118.2(6) . . ?
C9A C10A C11A 120.4(6) . . ?
C9A C10A H10A 119.8 . . ?
C11A C10A H10A 119.8 . . ?
C12A C11A C10A 118.6(6) . . ?
C12A C11A H11A 120.7 . . ?
C10A C11A H11A 120.7 . . ?
C13A C12A C11A 121.4(6) . . ?
C13A C12A H12A 119.3 . . ?
C11A C12A H12A 119.3 . . ?
C12A C13A C14A 118.4(6) . . ?
C12A C13A H13A 120.8 . . ?
C14A C13A H13A 120.8 . . ?
C9A C14A C13A 120.0(6) . . ?
C9A C14A H14A 120.0 . . ?
C13A C14A H14A 120.0 . . ?
C8A C15A H15A 109.5 . . ?
C8A C15A H15B 109.5 . . ?
H15A C15A H15B 109.5 . . ?
C8A C15A H15C 109.5 . . ?
H15A C15A H15C 109.5 . . ?
H15B C15A H15C 109.5 . . ?
C1B N1B C8B 121.7(5) . . ?
C1B N1B H1B 120(4) . . ?
C8B N1B H1B 117(4) . . ?
O1B C1B N1B 119.8(7) . . ?
O1B C1B C2B 122.4(6) . . ?
N1B C1B C2B 117.8(6) . . ?
C7B C2B C3B 120.3(9) . . ?
C7D C2B C3D 114.5(9) . . ?
C7B C2B C1B 124.8(7) . . ?
C3B C2B C1B 114.8(7) . . ?
C7D C2B C1B 124.8(7) . . ?
C3D C2B C1B 120.6(8) . . ?
C2B C3B C4B 119.7(9) . . ?
C2B C3B H3B 120.2 . . ?
C4B C3B H3B 120.2 . . ?
C5B C4B C3B 119.6(10) . . ?
C5B C4B H4B 120.2 . . ?
C3B C4B H4B 120.2 . . ?
C6D C5B C4D 125.7(9) . . ?
C4B C5B C6B 118.2(10) . . ?
C4B C5B H5B 120.9 . . ?
C6B C5B H5B 120.9 . . ?
C7B C6B C5B 121.0(12) . . ?
C7B C6B H6B 119.5 . . ?
C5B C6B H6B 119.5 . . ?
C2B C7B F2 120.8(11) . . ?
C2B C7B C6B 121.1(11) . . ?
F2 C7B C6B 118.1(11) . . ?
N1B C8B C9B 112.8(5) . . ?
N1B C8B C15B 109.2(5) . . ?
C9B C8B C15B 110.7(5) . . ?
N1B C8B H8B 108.0 . . ?
C9B C8B H8B 108.0 . . ?
C15B C8B H8B 108.0 . . ?
C14B C9B C10B 116.1(6) . . ?
C14B C9B C8B 121.1(6) . . ?
C10B C9B C8B 122.8(6) . . ?
C11B C10B C9B 120.5(6) . . ?
C11B C10B H10B 119.8 . . ?
C9B C10B H10B 119.8 . . ?
C12B C11B C10B 122.4(7) . . ?
C12B C11B H11B 118.8 . . ?
C10B C11B H11B 118.8 . . ?
C11B C12B C13B 117.2(7) . . ?
C11B C12B H12B 121.4 . . ?
C13B C12B H12B 121.4 . . ?
C14B C13B C12B 122.5(7) . . ?
C14B C13B H13B 118.7 . . ?
C12B C13B H13B 118.7 . . ?
C13B C14B C9B 121.3(6) . . ?
C13B C14B H14B 119.4 . . ?
C9B C14B H14B 119.4 . . ?
C8B C15B H15D 109.5 . . ?
C8B C15B H15E 109.5 . . ?
H15D C15B H15E 109.5 . . ?
C8B C15B H15F 109.5 . . ?
H15D C15B H15F 109.5 . . ?
H15E C15B H15F 109.5 . . ?
C4C C3C C2A 119.9(11) . . ?
C4C C3C H3C 120.0 . . ?
C2A C3C H3C 120.0 . . ?
C3C C4C C5A 120.8(11) . . ?
C3C C4C H4C 119.6 . . ?
C5A C4C H4C 119.6 . . ?
C7C C6C C5A 121.1(12) . . ?
C7C C6C H6C 119.4 . . ?
C5A C6C H6C 119.4 . . ?
C6C C7C C2A 122.8(11) . . ?
C6C C7C H7C 118.6 . . ?
C2A C7C H7C 118.6 . . ?
C2B C3D C4D 124.5(12) . . ?
C2B C3D H3D 117.8 . . ?
C4D C3D H3D 117.8 . . ?
C5B C4D C3D 115.5(11) . . ?
C5B C4D H4D 122.3 . . ?
C3D C4D H4D 122.3 . . ?
C5B C6D C7D 116.1(11) . . ?
C5B C6D H6D 122.0 . . ?
C7D C6D H6D 122.0 . . ?
F3 C7D C2B 122.7(12) . . ?
F3 C7D C6D 113.5(12) . . ?
C2B C7D C6D 123.5(10) . . ?

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
C8A N1A C1A O1A -6.2(9) . . . . ?
C8A N1A C1A C2A 176.4(5) . . . . ?
O1A C1A C2A C7A -157.0(8) . . . . ?
N1A C1A C2A C7A 20.6(10) . . . . ?
O1A C1A C2A C3A 26.8(10) . . . . ?
N1A C1A C2A C3A -155.6(8) . . . . ?
O1A C1A C2A C7C 144.5(7) . . . . ?
N1A C1A C2A C7C -37.8(9) . . . . ?
O1A C1A C2A C3C -32.5(9) . . . . ?
N1A C1A C2A C3C 145.1(7) . . . . ?
C7A C2A C3A C4A -1.3(17) . . . . ?
C1A C2A C3A C4A 175.0(10) . . . . ?
C2A C3A C4A C5A 6.6(19) . . . . ?
C3A C4A C5A C6A -6.0(16) . . . . ?
C4A C5A C6A C7A 0.2(14) . . . . ?
C5A C6A C7A C2A 4.6(16) . . . . ?
C3A C2A C7A C6A -4.3(16) . . . . ?
C1A C2A C7A C6A 179.7(8) . . . . ?
C1A N1A C8A C15A 146.9(5) . . . . ?
C1A N1A C8A C9A -87.5(7) . . . . ?
N1A C8A C9A C10A -57.1(7) . . . . ?
C15A C8A C9A C10A 66.9(8) . . . . ?
N1A C8A C9A C14A 126.0(6) . . . . ?
C15A C8A C9A C14A -110.0(7) . . . . ?
C14A C9A C10A C11A -3.1(10) . . . . ?
C8A C9A C10A C11A -179.9(5) . . . . ?
C9A C10A C11A C12A 3.5(9) . . . . ?
C10A C11A C12A C13A -2.0(9) . . . . ?
C11A C12A C13A C14A 0.1(9) . . . . ?
C10A C9A C14A C13A 1.1(10) . . . . ?
C8A C9A C14A C13A 177.9(5) . . . . ?
C12A C13A C14A C9A 0.4(9) . . . . ?
C8B N1B C1B O1B 3.1(9) . . . . ?
C8B N1B C1B C2B -174.5(5) . . . . ?
O1B C1B C2B C7B 153.3(8) . . . . ?
N1B C1B C2B C7B -29.2(11) . . . . ?
O1B C1B C2B C3B -26.2(10) . . . . ?
N1B C1B C2B C3B 151.3(7) . . . . ?
O1B C1B C2B C7D -142.5(8) . . . . ?
N1B C1B C2B C7D 35.0(10) . . . . ?
O1B C1B C2B C3D 35.5(10) . . . . ?
N1B C1B C2B C3D -147.0(7) . . . . ?
C7B C2B C3B C4B -0.4(14) . . . . ?
C1B C2B C3B C4B 179.1(8) . . . . ?
C2B C3B C4B C5B 1.5(15) . . . . ?
C3B C4B C5B C6B 0.2(15) . . . . ?
C4B C5B C6B C7B -3.1(18) . . . . ?
C3B C2B C7B F2 -180.0(9) . . . . ?
C1B C2B C7B F2 0.6(15) . . . . ?
C3B C2B C7B C6B -2.5(16) . . . . ?
C1B C2B C7B C6B 178.1(10) . . . . ?
C5B C6B C7B C2B 4(2) . . . . ?
C5B C6B C7B F2 -178.1(11) . . . . ?
C1B N1B C8B C9B 90.5(7) . . . . ?
C1B N1B C8B C15B -146.0(6) . . . . ?
N1B C8B C9B C14B -125.6(6) . . . . ?
C15B C8B C9B C14B 111.8(6) . . . . ?
N1B C8B C9B C10B 52.6(7) . . . . ?
C15B C8B C9B C10B -70.1(8) . . . . ?
C14B C9B C10B C11B -1.6(9) . . . . ?
C8B C9B C10B C11B -179.8(6) . . . . ?
C9B C10B C11B C12B 0.3(10) . . . . ?
C10B C11B C12B C13B 0.1(11) . . . . ?
C11B C12B C13B C14B 0.8(11) . . . . ?
C12B C13B C14B C9B -2.2(10) . . . . ?
C10B C9B C14B C13B 2.5(9) . . . . ?
C8B C9B C14B C13B -179.3(6) . . . . ?
C7C C2A C3C C4C -1.2(14) . . . . ?
C1A C2A C3C C4C 176.1(9) . . . . ?
C2A C3C C4C C5A -1.3(16) . . . . ?
C6C C5A C4C C3C 0.6(15) . . . . ?
C4C C5A C6C C7C 3.0(16) . . . . ?
C5A C6C C7C C2A -5.9(18) . . . . ?
C3C C2A C7C C6C 4.9(14) . . . . ?
C1A C2A C7C C6C -172.4(9) . . . . ?
C7D C2B C3D C4D 2.7(14) . . . . ?
C1B C2B C3D C4D -175.5(9) . . . . ?
C6D C5B C4D C3D -4.9(15) . . . . ?
C2B C3D C4D C5B 0.5(16) . . . . ?
C4D C5B C6D C7D 5.5(14) . . . . ?
C3D C2B C7D F3 -175.9(9) . . . . ?
C1B C2B C7D F3 2.2(14) . . . . ?
C3D C2B C7D C6D -2.1(13) . . . . ?
C1B C2B C7D C6D 176.0(8) . . . . ?
C5B C6D C7D F3 172.6(9) . . . . ?
C5B C6D C7D C2B -1.6(14) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1A H1A O1A 0.86(3) 2.33(3) 3.143(6) 157(6) 1_455
N1B H1B O1B 0.87(3) 2.32(3) 3.122(7) 154(5) 1_655
N1A H1A O1A 0.86(3) 2.33(3) 3.143(6) 157(6) 1_455
N1B H1B O1B 0.87(3) 2.32(3) 3.122(7) 154(5) 1_655
N1A H1A O1A 0.86(3) 2.33(3) 3.143(6) 157(6) 1_455
N1B H1B O1B 0.87(3) 2.32(3) 3.122(7) 154(5) 1_655

_refine_diff_density_max         0.638
_refine_diff_density_min         -0.204
_refine_diff_density_rms         0.066

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: 1:1 hexanes:dichloromethane '
####################################################################### 
# 
# 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_16kaw97
_database_code_depnum_ccdc_archive 'CCDC 1534591'
_audit_update_record             
;
2017-02-23 deposited with the CCDC.
2017-03-31 downloaded from the CCDC.
;



_audit_creation_method           SHELXL-2014/7
#_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H14 F3 N O, C15 H14 N2 O3'
_chemical_formula_sum            'C31 H28 F3 N3 O4'
_chemical_formula_weight         563.56

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0727 0.0534 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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.
;

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

_cell_length_a                   8.3035(14)
_cell_length_b                   9.6853(13)
_cell_length_c                   17.333(3)
_cell_angle_alpha                90
_cell_angle_beta                 101.057(9)
_cell_angle_gamma                90
_cell_volume                     1368.0(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6205
_cell_measurement_theta_min      2.60
_cell_measurement_theta_max      67.96
_exptl_crystal_description       'transparent plate'
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.368
_exptl_crystal_F_000             588
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.264
_exptl_crystal_size_mid          0.097
_exptl_crystal_size_min          0.032
_exptl_absorpt_coefficient_mu    0.882
_shelx_estimated_absorpt_T_min   0.800
_shelx_estimated_absorpt_T_max   0.972
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.591
_exptl_absorpt_correction_T_max  0.753
_exptl_absorpt_process_details   'SADABS-2014/7, Bruker AXS'
#_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 8.33
_diffrn_reflns_number            20018
_diffrn_reflns_av_unetI/netI     0.0795
_diffrn_reflns_av_R_equivalents  0.0992
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.597
_diffrn_reflns_theta_max         68.220
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_point_group_measured_fraction_full 0.984
_reflns_number_total             4899
_reflns_number_gt                3797
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.847
_reflns_Friedel_fraction_max     0.959
_reflns_Friedel_fraction_full    0.967

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 

;


_computing_data_collection       'APEX2 (Bruker, 2013)'
_computing_cell_refinement       APEX2
_computing_data_reduction        
;
SADABS (Bruker, 2013) and XPREP (Bruker, 2013)
;
_computing_structure_solution    'SHELXS-2014/7 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'XSEED (Barbour, 2001)'
_computing_publication_material  'XSEED (Barbour, 2001)'

_refine_special_details          
;
All nonhydrogen atoms were located in a succesive difference Fourier electron
 density maps and refined using anisotropic diplacement parameters. All C-H
 hydrogen atoms were placed in calculated positions with Uiso = 1.2xUeqiv
 (1.5Ueq for methyl groups) of the connected C atoms. Those H atoms attached
 to nitrogen were located in Fourier diff maps and assigned Uiso = 1.2xUeqiv
 with N-H bond distances restrained to 0.85(2) angstroms.
;


_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0891P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 1329 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.23(15)
_chemical_absolute_configuration rm
_refine_ls_number_reflns         4899
_refine_ls_number_parameters     380
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0787
_refine_ls_R_factor_gt           0.0616
_refine_ls_wR_factor_ref         0.1708
_refine_ls_wR_factor_gt          0.1599
_refine_ls_goodness_of_fit_ref   1.061
_refine_ls_restrained_S_all      1.061
_refine_ls_shift/su_max          0.003
_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_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 0.2896(5) 0.3657(4) 0.1217(2) 0.0425(9) Uani 1 1 d . . . . .
F2 F 0.2999(5) 0.5864(4) 0.1389(2) 0.0411(10) Uani 1 1 d . . . . .
F3 F 0.3293(5) 0.4487(4) 0.2383(2) 0.0444(10) Uani 1 1 d . . . . .
O1 O 0.0009(7) 0.7265(4) 0.0217(3) 0.0354(11) Uani 1 1 d . . . . .
O1A O 0.4981(7) 0.4466(4) 0.4817(3) 0.0373(12) Uani 1 1 d . . . . .
O2A O 0.1685(6) 0.8119(5) 0.3133(3) 0.0530(13) Uani 1 1 d . . . . .
O3A O 0.1950(6) 0.6164(5) 0.3761(3) 0.0401(12) Uani 1 1 d . . . . .
N1 N 0.0710(7) 0.5161(5) -0.0194(3) 0.0286(12) Uani 1 1 d . . . . .
H2 H 0.063(13) 0.411(11) -0.014(6) 0.09(4) Uiso 1 1 d . . . . .
N1A N 0.4333(7) 0.6584(5) 0.5248(3) 0.0260(12) Uani 1 1 d . . . . .
H2A H 0.438(7) 0.746(7) 0.515(3) 0.020(16) Uiso 1 1 d . . . . .
N2A N 0.2518(8) 0.7156(5) 0.3464(3) 0.0346(13) Uani 1 1 d . . . . .
C1 C 0.0122(8) 0.5999(6) 0.0294(3) 0.0267(14) Uani 1 1 d . . . . .
C2 C -0.0452(8) 0.5302(6) 0.0982(3) 0.0249(13) Uani 1 1 d . . . . .
C3 C 0.0588(8) 0.4711(6) 0.1622(3) 0.0253(13) Uani 1 1 d . . . . .
C4 C -0.0001(10) 0.4147(6) 0.2243(4) 0.0360(16) Uani 1 1 d . . . . .
H4 H 0.0736 0.3757 0.2675 0.043 Uiso 1 1 calc R U . . .
C5 C -0.1664(10) 0.4152(7) 0.2233(4) 0.0390(17) Uani 1 1 d . . . . .
H5 H -0.2073 0.3750 0.2657 0.047 Uiso 1 1 calc R U . . .
C6 C -0.2735(9) 0.4732(7) 0.1615(4) 0.0353(15) Uani 1 1 d . . . . .
H6 H -0.3880 0.4744 0.1615 0.042 Uiso 1 1 calc R U . . .
C7 C -0.2132(8) 0.5307(6) 0.0987(4) 0.0291(14) Uani 1 1 d . . . . .
H7 H -0.2873 0.5704 0.0558 0.035 Uiso 1 1 calc R U . . .
C8 C 0.1388(9) 0.5652(6) -0.0868(4) 0.0310(15) Uani 1 1 d . . . . .
H8 H 0.1425 0.6684 -0.0847 0.037 Uiso 1 1 calc R U . . .
C9 C 0.0301(9) 0.5232(9) -0.1640(4) 0.0416(18) Uani 1 1 d . . . . .
H9A H 0.0214 0.4223 -0.1666 0.062 Uiso 1 1 calc R U . . .
H9B H 0.0781 0.5568 -0.2079 0.062 Uiso 1 1 calc R U . . .
H9C H -0.0794 0.5633 -0.1673 0.062 Uiso 1 1 calc R U . . .
C10 C 0.3104(8) 0.5137(6) -0.0844(3) 0.0263(13) Uani 1 1 d . . . . .
C11 C 0.4259(9) 0.5955(7) -0.1115(3) 0.0323(15) Uani 1 1 d . . . . .
H11 H 0.3970 0.6870 -0.1285 0.039 Uiso 1 1 calc R U . . .
C12 C 0.5803(9) 0.5475(6) -0.1143(4) 0.0317(15) Uani 1 1 d . . . . .
H12 H 0.6553 0.6057 -0.1339 0.038 Uiso 1 1 calc R U . . .
C13 C 0.6288(9) 0.4138(6) -0.0887(4) 0.0287(14) Uani 1 1 d . . . . .
H13 H 0.7356 0.3807 -0.0907 0.034 Uiso 1 1 calc R U . . .
C14 C 0.5171(9) 0.3318(6) -0.0604(4) 0.0333(15) Uani 1 1 d . . . . .
H14 H 0.5477 0.2410 -0.0427 0.040 Uiso 1 1 calc R U . . .
C15 C 0.3608(9) 0.3798(6) -0.0574(4) 0.0328(15) Uani 1 1 d . . . . .
H15 H 0.2867 0.3219 -0.0368 0.039 Uiso 1 1 calc R U . . .
C16 C 0.2429(8) 0.4698(6) 0.1658(3) 0.0286(14) Uani 1 1 d . . . . .
C1A C 0.4860(8) 0.5747(6) 0.4742(4) 0.0254(14) Uani 1 1 d . . . . .
C2A C 0.5373(8) 0.6445(6) 0.4052(3) 0.0262(14) Uani 1 1 d . . . . .
C3A C 0.4282(9) 0.7157(6) 0.3468(3) 0.0277(14) Uani 1 1 d . . . . .
C4A C 0.4810(10) 0.7835(6) 0.2845(4) 0.0329(15) Uani 1 1 d . . . . .
H4A H 0.4050 0.8323 0.2461 0.039 Uiso 1 1 calc R U . . .
C5A C 0.6459(9) 0.7783(6) 0.2797(4) 0.0360(17) Uani 1 1 d . . . . .
H5A H 0.6835 0.8225 0.2376 0.043 Uiso 1 1 calc R U . . .
C6A C 0.7552(10) 0.7082(7) 0.3367(4) 0.0372(17) Uani 1 1 d . . . . .
H6A H 0.8681 0.7051 0.3334 0.045 Uiso 1 1 calc R U . . .
C7A C 0.7023(8) 0.6424(6) 0.3986(4) 0.0295(14) Uani 1 1 d . . . . .
H7A H 0.7797 0.5952 0.4372 0.035 Uiso 1 1 calc R U . . .
C8A C 0.3614(8) 0.6098(6) 0.5913(3) 0.0272(14) Uani 1 1 d . . . . .
H8A H 0.3611 0.5066 0.5905 0.033 Uiso 1 1 calc R U . . .
C9A C 0.4703(10) 0.6570(8) 0.6686(4) 0.0415(17) Uani 1 1 d . . . . .
H9A1 H 0.5795 0.6158 0.6733 0.062 Uiso 1 1 calc R U . . .
H9A2 H 0.4211 0.6274 0.7129 0.062 Uiso 1 1 calc R U . . .
H9A3 H 0.4797 0.7578 0.6688 0.062 Uiso 1 1 calc R U . . .
C10A C 0.1856(8) 0.6582(6) 0.5841(3) 0.0264(14) Uani 1 1 d . . . . .
C11A C 0.0718(9) 0.5788(6) 0.6137(4) 0.0310(15) Uani 1 1 d . . . . .
H11A H 0.1036 0.4901 0.6345 0.037 Uiso 1 1 calc R U . . .
C12A C -0.0868(9) 0.6244(7) 0.6140(4) 0.0346(15) Uani 1 1 d . . . . .
H12A H -0.1629 0.5668 0.6333 0.042 Uiso 1 1 calc R U . . .
C13A C -0.1317(9) 0.7557(7) 0.5857(3) 0.0336(16) Uani 1 1 d . . . . .
H13A H -0.2384 0.7899 0.5871 0.040 Uiso 1 1 calc R U . . .
C14A C -0.0215(9) 0.8372(7) 0.5555(4) 0.0341(15) Uani 1 1 d . . . . .
H14A H -0.0542 0.9259 0.5348 0.041 Uiso 1 1 calc R U . . .
C15A C 0.1365(8) 0.7903(6) 0.5550(4) 0.0304(14) Uani 1 1 d . . . . .
H15A H 0.2116 0.8476 0.5349 0.036 Uiso 1 1 calc R U . . .


_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 1.366(7) . ?
F2 C16 1.342(7) . ?
F3 C16 1.338(7) . ?
O1 C1 1.235(8) . ?
O1A C1A 1.250(7) . ?
O2A N2A 1.234(7) . ?
O3A N2A 1.227(7) . ?
N1 C1 1.331(8) . ?
N1 C8 1.469(8) . ?
N1 H2 1.03(11) . ?
N1A C1A 1.329(8) . ?
N1A C8A 1.473(8) . ?
N1A H2A 0.87(6) . ?
N2A C3A 1.463(9) . ?
C1 C2 1.523(8) . ?
C2 C3 1.391(8) . ?
C2 C7 1.396(9) . ?
C3 C4 1.378(9) . ?
C3 C16 1.518(9) . ?
C4 C5 1.378(11) . ?
C4 H4 0.9500 . ?
C5 C6 1.375(10) . ?
C5 H5 0.9500 . ?
C6 C7 1.399(9) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 C10 1.503(9) . ?
C8 C9 1.519(9) . ?
C8 H8 1.0000 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.393(9) . ?
C10 C15 1.415(8) . ?
C11 C12 1.373(9) . ?
C11 H11 0.9500 . ?
C12 C13 1.403(9) . ?
C12 H12 0.9500 . ?
C13 C14 1.381(9) . ?
C13 H13 0.9500 . ?
C14 C15 1.389(9) . ?
C14 H14 0.9500 . ?
C15 H15 0.9500 . ?
C1A C2A 1.504(8) . ?
C2A C7A 1.396(9) . ?
C2A C3A 1.404(9) . ?
C3A C4A 1.404(8) . ?
C4A C5A 1.389(10) . ?
C4A H4A 0.9500 . ?
C5A C6A 1.384(10) . ?
C5A H5A 0.9500 . ?
C6A C7A 1.391(9) . ?
C6A H6A 0.9500 . ?
C7A H7A 0.9500 . ?
C8A C10A 1.515(9) . ?
C8A C9A 1.535(9) . ?
C8A H8A 1.0000 . ?
C9A H9A1 0.9800 . ?
C9A H9A2 0.9800 . ?
C9A H9A3 0.9800 . ?
C10A C11A 1.390(9) . ?
C10A C15A 1.407(9) . ?
C11A C12A 1.389(10) . ?
C11A H11A 0.9500 . ?
C12A C13A 1.389(9) . ?
C12A H12A 0.9500 . ?
C13A C14A 1.386(10) . ?
C13A H13A 0.9500 . ?
C14A C15A 1.389(9) . ?
C14A H14A 0.9500 . ?
C15A H15A 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C8 123.5(5) . . ?
C1 N1 H2 120(6) . . ?
C8 N1 H2 116(6) . . ?
C1A N1A C8A 123.8(5) . . ?
C1A N1A H2A 116(4) . . ?
C8A N1A H2A 120(4) . . ?
O3A N2A O2A 124.1(6) . . ?
O3A N2A C3A 117.6(5) . . ?
O2A N2A C3A 118.2(5) . . ?
O1 C1 N1 124.5(6) . . ?
O1 C1 C2 119.7(5) . . ?
N1 C1 C2 115.8(5) . . ?
C3 C2 C7 117.7(6) . . ?
C3 C2 C1 124.5(6) . . ?
C7 C2 C1 117.8(5) . . ?
C4 C3 C2 121.8(6) . . ?
C4 C3 C16 118.0(5) . . ?
C2 C3 C16 120.2(5) . . ?
C5 C4 C3 119.6(6) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
C6 C5 C4 120.5(6) . . ?
C6 C5 H5 119.7 . . ?
C4 C5 H5 119.7 . . ?
C5 C6 C7 119.6(7) . . ?
C5 C6 H6 120.2 . . ?
C7 C6 H6 120.2 . . ?
C2 C7 C6 120.7(6) . . ?
C2 C7 H7 119.6 . . ?
C6 C7 H7 119.6 . . ?
N1 C8 C10 112.1(5) . . ?
N1 C8 C9 111.1(6) . . ?
C10 C8 C9 109.6(5) . . ?
N1 C8 H8 108.0 . . ?
C10 C8 H8 108.0 . . ?
C9 C8 H8 108.0 . . ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C8 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 C15 117.0(6) . . ?
C11 C10 C8 120.8(6) . . ?
C15 C10 C8 122.2(6) . . ?
C12 C11 C10 121.8(6) . . ?
C12 C11 H11 119.1 . . ?
C10 C11 H11 119.1 . . ?
C11 C12 C13 121.0(6) . . ?
C11 C12 H12 119.5 . . ?
C13 C12 H12 119.5 . . ?
C14 C13 C12 118.2(6) . . ?
C14 C13 H13 120.9 . . ?
C12 C13 H13 120.9 . . ?
C13 C14 C15 121.1(6) . . ?
C13 C14 H14 119.4 . . ?
C15 C14 H14 119.4 . . ?
C14 C15 C10 120.9(6) . . ?
C14 C15 H15 119.6 . . ?
C10 C15 H15 119.6 . . ?
F3 C16 F2 107.1(5) . . ?
F3 C16 F1 104.7(5) . . ?
F2 C16 F1 105.7(5) . . ?
F3 C16 C3 113.2(5) . . ?
F2 C16 C3 113.5(5) . . ?
F1 C16 C3 112.0(5) . . ?
O1A C1A N1A 124.5(6) . . ?
O1A C1A C2A 120.0(6) . . ?
N1A C1A C2A 115.5(5) . . ?
C7A C2A C3A 117.2(6) . . ?
C7A C2A C1A 119.3(5) . . ?
C3A C2A C1A 123.5(6) . . ?
C2A C3A C4A 122.0(6) . . ?
C2A C3A N2A 120.7(5) . . ?
C4A C3A N2A 117.2(6) . . ?
C5A C4A C3A 119.1(6) . . ?
C5A C4A H4A 120.5 . . ?
C3A C4A H4A 120.5 . . ?
C6A C5A C4A 119.7(6) . . ?
C6A C5A H5A 120.2 . . ?
C4A C5A H5A 120.2 . . ?
C5A C6A C7A 121.0(7) . . ?
C5A C6A H6A 119.5 . . ?
C7A C6A H6A 119.5 . . ?
C6A C7A C2A 121.1(6) . . ?
C6A C7A H7A 119.5 . . ?
C2A C7A H7A 119.5 . . ?
N1A C8A C10A 111.5(5) . . ?
N1A C8A C9A 109.2(6) . . ?
C10A C8A C9A 112.1(5) . . ?
N1A C8A H8A 108.0 . . ?
C10A C8A H8A 108.0 . . ?
C9A C8A H8A 108.0 . . ?
C8A C9A H9A1 109.5 . . ?
C8A C9A H9A2 109.5 . . ?
H9A1 C9A H9A2 109.5 . . ?
C8A C9A H9A3 109.5 . . ?
H9A1 C9A H9A3 109.5 . . ?
H9A2 C9A H9A3 109.5 . . ?
C11A C10A C15A 117.7(6) . . ?
C11A C10A C8A 120.7(6) . . ?
C15A C10A C8A 121.2(6) . . ?
C12A C11A C10A 122.5(6) . . ?
C12A C11A H11A 118.7 . . ?
C10A C11A H11A 118.7 . . ?
C13A C12A C11A 118.7(7) . . ?
C13A C12A H12A 120.7 . . ?
C11A C12A H12A 120.7 . . ?
C14A C13A C12A 120.2(7) . . ?
C14A C13A H13A 119.9 . . ?
C12A C13A H13A 119.9 . . ?
C13A C14A C15A 120.6(6) . . ?
C13A C14A H14A 119.7 . . ?
C15A C14A H14A 119.7 . . ?
C14A C15A C10A 120.3(6) . . ?
C14A C15A H15A 119.9 . . ?
C10A C15A H15A 119.9 . . ?

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
C8 N1 C1 O1 3.5(11) . . . . ?
C8 N1 C1 C2 -177.1(6) . . . . ?
O1 C1 C2 C3 -109.2(8) . . . . ?
N1 C1 C2 C3 71.3(8) . . . . ?
O1 C1 C2 C7 67.9(8) . . . . ?
N1 C1 C2 C7 -111.5(7) . . . . ?
C7 C2 C3 C4 0.0(8) . . . . ?
C1 C2 C3 C4 177.2(5) . . . . ?
C7 C2 C3 C16 -178.8(5) . . . . ?
C1 C2 C3 C16 -1.7(8) . . . . ?
C2 C3 C4 C5 0.5(9) . . . . ?
C16 C3 C4 C5 179.4(6) . . . . ?
C3 C4 C5 C6 -1.0(9) . . . . ?
C4 C5 C6 C7 0.9(10) . . . . ?
C3 C2 C7 C6 -0.1(8) . . . . ?
C1 C2 C7 C6 -177.5(5) . . . . ?
C5 C6 C7 C2 -0.3(9) . . . . ?
C1 N1 C8 C10 124.6(7) . . . . ?
C1 N1 C8 C9 -112.4(7) . . . . ?
N1 C8 C10 C11 -145.1(6) . . . . ?
C9 C8 C10 C11 91.1(7) . . . . ?
N1 C8 C10 C15 37.0(8) . . . . ?
C9 C8 C10 C15 -86.8(7) . . . . ?
C15 C10 C11 C12 2.0(9) . . . . ?
C8 C10 C11 C12 -176.0(6) . . . . ?
C10 C11 C12 C13 -1.0(10) . . . . ?
C11 C12 C13 C14 -0.1(9) . . . . ?
C12 C13 C14 C15 0.1(10) . . . . ?
C13 C14 C15 C10 1.0(10) . . . . ?
C11 C10 C15 C14 -2.0(9) . . . . ?
C8 C10 C15 C14 175.9(6) . . . . ?
C4 C3 C16 F3 -17.6(7) . . . . ?
C2 C3 C16 F3 161.3(5) . . . . ?
C4 C3 C16 F2 -139.9(5) . . . . ?
C2 C3 C16 F2 38.9(7) . . . . ?
C4 C3 C16 F1 100.5(6) . . . . ?
C2 C3 C16 F1 -80.6(7) . . . . ?
C8A N1A C1A O1A -8.4(10) . . . . ?
C8A N1A C1A C2A 173.3(6) . . . . ?
O1A C1A C2A C7A -65.7(8) . . . . ?
N1A C1A C2A C7A 112.7(7) . . . . ?
O1A C1A C2A C3A 115.9(7) . . . . ?
N1A C1A C2A C3A -65.7(8) . . . . ?
C7A C2A C3A C4A -0.5(8) . . . . ?
C1A C2A C3A C4A 177.9(5) . . . . ?
C7A C2A C3A N2A 176.1(5) . . . . ?
C1A C2A C3A N2A -5.4(8) . . . . ?
O3A N2A C3A C2A -27.2(8) . . . . ?
O2A N2A C3A C2A 155.9(6) . . . . ?
O3A N2A C3A C4A 149.6(5) . . . . ?
O2A N2A C3A C4A -27.4(8) . . . . ?
C2A C3A C4A C5A 1.0(9) . . . . ?
N2A C3A C4A C5A -175.7(5) . . . . ?
C3A C4A C5A C6A -0.8(9) . . . . ?
C4A C5A C6A C7A 0.3(9) . . . . ?
C5A C6A C7A C2A 0.2(9) . . . . ?
C3A C2A C7A C6A -0.1(8) . . . . ?
C1A C2A C7A C6A -178.6(5) . . . . ?
C1A N1A C8A C10A -118.1(6) . . . . ?
C1A N1A C8A C9A 117.4(6) . . . . ?
N1A C8A C10A C11A 148.8(5) . . . . ?
C9A C8A C10A C11A -88.5(7) . . . . ?
N1A C8A C10A C15A -37.9(8) . . . . ?
C9A C8A C10A C15A 84.9(7) . . . . ?
C15A C10A C11A C12A 1.1(9) . . . . ?
C8A C10A C11A C12A 174.7(6) . . . . ?
C10A C11A C12A C13A -1.8(9) . . . . ?
C11A C12A C13A C14A 2.1(9) . . . . ?
C12A C13A C14A C15A -1.8(10) . . . . ?
C13A C14A C15A C10A 1.1(10) . . . . ?
C11A C10A C15A C14A -0.7(9) . . . . ?
C8A C10A C15A C14A -174.2(5) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H2 O1 1.03(11) 1.86(11) 2.867(6) 166(9) 2_545
N1A H2A O1A 0.87(6) 2.01(6) 2.856(6) 164(6) 2_656

_refine_diff_density_max         0.341
_refine_diff_density_min         -0.350
_refine_diff_density_rms         0.082


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: 1:1 hexanes:dichloromethane '
