# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_BD71m
_database_code_depnum_ccdc_archive 'CCDC 1505772'
_audit_update_record             
;
2016-09-22 deposited with the CCDC.
2016-10-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
'2-(4-Fluoro-2-(4-(trifluoromethyl)benzamido)phenyl)-6-phenyl-5,6-dihydro-4H-1,3-oxazin-5-yl acetate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H20 F4 N2 O4'
_chemical_formula_sum            'C26 H20 F4 N2 O4'
_chemical_formula_weight         500.44

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_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'
'-x, -y, -z'

_cell_length_a                   9.7279(17)
_cell_length_b                   11.657(2)
_cell_length_c                   22.965(4)
_cell_angle_alpha                76.436(3)
_cell_angle_beta                 80.414(3)
_cell_angle_gamma                70.405(3)
_cell_volume                     2373.8(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    294(2)
_cell_measurement_reflns_used    5583
_cell_measurement_theta_min      2.25
_cell_measurement_theta_max      22.68

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.400
_exptl_crystal_F_000             1032
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.116
_shelx_estimated_absorpt_T_min   0.979
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.92
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_process_details   'SADABS; Bruker,2001'

_diffrn_ambient_temperature      294(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_measurement_device_type  'Bruker SMART APEX CCD area-detector'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            23019
_diffrn_reflns_av_unetI/netI     0.0353
_diffrn_reflns_av_R_equivalents  0.0286
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         1.833
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             8336
_reflns_number_gt                5234
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       'SMART (Bruker, 2001)'
_computing_cell_refinement       'SAINT (Bruker, 2001)'
_computing_data_reduction        'SAINT (Bruker, 2001)'
_computing_structure_solution    'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2015)'
_computing_molecular_graphics    'SHELXL2014 (Sheldrick, 2015)'
_computing_publication_material  'SHELXL2014 (Sheldrick, 2015)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1250P)²+0.7774P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8336
_refine_ls_number_parameters     679
_refine_ls_number_restraints     54
_refine_ls_R_factor_all          0.1051
_refine_ls_R_factor_gt           0.0717
_refine_ls_wR_factor_ref         0.2363
_refine_ls_wR_factor_gt          0.2042
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.047
_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
C1A C 0.4979(3) 0.6841(3) 0.65090(12) 0.0552(7) Uani 1 1 d . . . . .
C2A C 0.6011(3) 0.7283(3) 0.66769(12) 0.0547(7) Uani 1 1 d . . . . .
C3A C 0.6802(3) 0.7914(3) 0.62292(13) 0.0636(8) Uani 1 1 d . . . . .
H3A H 0.7482 0.8221 0.6329 0.076 Uiso 1 1 calc R U . . .
C4A C 0.6557(4) 0.8074(3) 0.56411(14) 0.0732(9) Uani 1 1 d . . . . .
C5A C 0.5580(4) 0.7658(3) 0.54633(14) 0.0763(9) Uani 1 1 d . . . . .
H5A H 0.5442 0.7786 0.5059 0.092 Uiso 1 1 calc R U . . .
C6A C 0.4798(3) 0.7036(3) 0.59055(13) 0.0657(8) Uani 1 1 d . . . . .
H6A H 0.4125 0.6737 0.5794 0.079 Uiso 1 1 calc R U . . .
C7A C 0.4049(3) 0.6205(3) 0.69587(13) 0.0592(7) Uani 1 1 d . . . . .
C8A C 0.1967(3) 0.5491(3) 0.70464(14) 0.0691(8) Uani 1 1 d . . . . .
H8A H 0.1209 0.6244 0.7138 0.083 Uiso 1 1 calc R U . . .
C9A C 0.2522(4) 0.4675(3) 0.76220(14) 0.0745(9) Uani 1 1 d . . . . .
H9A H 0.3243 0.3894 0.7543 0.089 Uiso 1 1 calc R U . . .
C10A C 0.3194(4) 0.5348(4) 0.79291(15) 0.0832(10) Uani 1 1 d . . . . .
H10A H 0.2413 0.5922 0.8137 0.100 Uiso 1 1 calc R U . . .
H10B H 0.3795 0.4747 0.8229 0.100 Uiso 1 1 calc R U . . .
C11A C 0.1369(3) 0.4907(3) 0.66611(14) 0.0625(7) Uani 1 1 d . . . . .
C12A C 0.2229(4) 0.3893(4) 0.64245(18) 0.0852(10) Uani 1 1 d . . . . .
H12A H 0.3187 0.3509 0.6525 0.102 Uiso 1 1 calc R U . . .
C13A C 0.1692(5) 0.3436(4) 0.60388(19) 0.0939(11) Uani 1 1 d . . . . .
H13A H 0.2293 0.2760 0.5873 0.113 Uiso 1 1 calc R U . . .
C14A C 0.0283(5) 0.3975(4) 0.59022(19) 0.0926(11) Uani 1 1 d . . . . .
H14A H -0.0088 0.3664 0.5647 0.111 Uiso 1 1 calc R U . . .
C15A C -0.0575(4) 0.4963(4) 0.6138(2) 0.1018(13) Uani 1 1 d . . . . .
H15A H -0.1541 0.5330 0.6046 0.122 Uiso 1 1 calc R U . . .
C16A C -0.0037(4) 0.5431(3) 0.65144(17) 0.0804(10) Uani 1 1 d . . . . .
H16A H -0.0642 0.6117 0.6672 0.097 Uiso 1 1 calc R U . . .
C17A C 0.1475(6) 0.3330(6) 0.83467(19) 0.1058(15) Uani 1 1 d . . . . .
C18A C 0.0138(6) 0.3271(6) 0.8773(2) 0.153(2) Uani 1 1 d . . . . .
H18A H 0.0268 0.2431 0.8982 0.229 Uiso 1 1 calc R U . . .
H18B H -0.0705 0.3552 0.8551 0.229 Uiso 1 1 calc R U . . .
H18C H -0.0001 0.3792 0.9059 0.229 Uiso 1 1 calc R U . . .
C19A C 0.7151(3) 0.7382(3) 0.75472(14) 0.0661(8) Uani 1 1 d . . . . .
C20A C 0.7110(3) 0.6999(3) 0.82150(14) 0.0722(9) Uani 1 1 d . . . . .
C21A C 0.6135(5) 0.6456(6) 0.85695(17) 0.1272(19) Uani 1 1 d . . . . .
H21A H 0.5438 0.6304 0.8392 0.153 Uiso 1 1 calc R U . . .
C22A C 0.6165(6) 0.6129(6) 0.91838(18) 0.145(2) Uani 1 1 d . . . . .
H22A H 0.5500 0.5751 0.9417 0.174 Uiso 1 1 calc R U . . .
C23A C 0.7175(5) 0.6359(5) 0.94509(18) 0.1078(14) Uani 1 1 d . . . . .
C24A C 0.8145(5) 0.6895(5) 0.91072(19) 0.1087(14) Uani 1 1 d . . . . .
H24A H 0.8839 0.7049 0.9286 0.130 Uiso 1 1 calc R U . . .
C25A C 0.8109(4) 0.7212(4) 0.84970(17) 0.0938(12) Uani 1 1 d . . . . .
H25A H 0.8783 0.7583 0.8267 0.113 Uiso 1 1 calc R U . . .
C26A C 0.7179(9) 0.5999(10) 1.0116(3) 0.169(3) Uani 1 1 d . . . . .
F1A F 0.7346(3) 0.8692(2) 0.52201(9) 0.1067(7) Uani 1 1 d . . . . .
F2A F 0.8367(6) 0.5164(7) 1.02838(19) 0.255(3) Uani 1 1 d . . . . .
F3A F 0.7215(9) 0.6916(6) 1.03493(17) 0.275(3) Uani 1 1 d . . . . .
F4A F 0.6166(6) 0.5644(6) 1.04095(14) 0.244(3) Uani 1 1 d . . . . .
N1A N 0.4091(3) 0.6034(2) 0.75188(11) 0.0673(7) Uani 1 1 d . . . . .
N2A N 0.6211(3) 0.7072(2) 0.72851(10) 0.0624(6) Uani 1 1 d . . . . .
H2A H 0.5660 0.6692 0.7528 0.075 Uiso 1 1 calc R U . . .
O1A O 0.3193(2) 0.5828(2) 0.66811(9) 0.0742(6) Uani 1 1 d . . . . .
O2A O 0.1277(3) 0.4442(3) 0.80020(11) 0.0910(7) Uani 1 1 d . . . . .
O3A O 0.2577(6) 0.2514(4) 0.8313(2) 0.176(2) Uani 1 1 d . . . . .
O4A O 0.8000(3) 0.7936(2) 0.72676(10) 0.0852(7) Uani 1 1 d . . . . .
C1B C 0.6718(3) 1.0028(3) 0.31505(13) 0.0554(7) Uani 1 1 d . . . . .
C2B C 0.7639(3) 1.0578(3) 0.27094(13) 0.0594(7) Uani 1 1 d . . . . .
C3B C 0.8671(3) 1.0974(3) 0.28970(14) 0.0652(8) Uani 1 1 d . . . . .
H3B H 0.9292 1.1327 0.2615 0.078 Uiso 1 1 calc R U . . .
C4B C 0.8757(3) 1.0836(3) 0.34938(14) 0.0652(8) Uani 1 1 d . . . . .
C5B C 0.7911(3) 1.0293(3) 0.39340(14) 0.0659(8) Uani 1 1 d . . . . .
H5B H 0.8021 1.0189 0.4340 0.079 Uiso 1 1 calc R U . . .
C6B C 0.6891(3) 0.9905(3) 0.37494(13) 0.0626(7) Uani 1 1 d . . . . .
H6B H 0.6293 0.9546 0.4041 0.075 Uiso 1 1 calc R U . . .
C7B C 0.5582(3) 0.9594(3) 0.29910(13) 0.0599(7) Uani 1 1 d . . . . .
C8B C 0.3536(3) 0.8872(3) 0.34170(14) 0.0683(8) Uani 1 1 d . . . . .
H8B H 0.2804 0.9697 0.3376 0.082 Uiso 1 1 calc R U . . .
C9B C 0.3685(4) 0.8420(3) 0.28503(15) 0.0754(9) Uani 1 1 d . . . . .
H9B H 0.4398 0.7587 0.2882 0.090 Uiso 1 1 calc R U . . .
C10B C 0.4182(4) 0.9284(4) 0.23228(15) 0.0797(10) Uani 1 1 d . . . . .
H10C H 0.4582 0.8848 0.1991 0.096 Uiso 1 1 calc R U . . .
H10D H 0.3338 0.9980 0.2195 0.096 Uiso 1 1 calc R U . . .
C11B C 0.3074(3) 0.8076(3) 0.39855(13) 0.0622(8) Uani 1 1 d . . . . .
C12B C 0.2004(4) 0.8629(3) 0.43875(15) 0.0790(9) Uani 1 1 d . . . . .
H12B H 0.1592 0.9488 0.4311 0.095 Uiso 1 1 calc R U . . .
C13B C 0.1523(4) 0.7935(5) 0.49056(16) 0.0946(12) Uani 1 1 d . . . . .
H13B H 0.0782 0.8329 0.5171 0.114 Uiso 1 1 calc R U . . .
C14B C 0.2120(5) 0.6688(5) 0.50302(17) 0.0912(12) Uani 1 1 d . . . . .
H14B H 0.1801 0.6225 0.5382 0.109 Uiso 1 1 calc R U . . .
C15B C 0.3187(5) 0.6115(4) 0.4638(2) 0.0970(12) Uani 1 1 d . . . . .
H15B H 0.3603 0.5257 0.4721 0.116 Uiso 1 1 calc R U . . .
C16B C 0.3655(4) 0.6801(4) 0.41184(19) 0.0892(11) Uani 1 1 d . . . . .
H16B H 0.4379 0.6398 0.3850 0.107 Uiso 1 1 calc R U . . .
C17B C 0.2193(6) 0.7391(5) 0.26118(18) 0.0932(11) Uani 1 1 d . . . . .
C18B C 0.0653(5) 0.7519(5) 0.2542(2) 0.1277(18) Uani 1 1 d . . . . .
H18D H 0.0601 0.6744 0.2486 0.192 Uiso 1 1 calc R U . . .
H18E H 0.0327 0.8152 0.2198 0.192 Uiso 1 1 calc R U . . .
H18F H 0.0037 0.7743 0.2896 0.192 Uiso 1 1 calc R U . . .
C19B C 0.8173(4) 1.1247(4) 0.16138(15) 0.0828(10) Uani 1 1 d . . . . .
C20B C 0.7824(4) 1.1147(4) 0.10202(15) 0.0836(10) Uani 1 1 d . . . . .
C21B C 0.7126(7) 1.0418(6) 0.09363(19) 0.137(2) Uani 1 1 d . . . . .
H21B H 0.6793 0.9917 0.1269 0.164 Uiso 1 1 calc R U . . .
C22B C 0.6870(7) 1.0372(7) 0.0370(2) 0.162(3) Uani 1 1 d . . . . .
H22B H 0.6362 0.9846 0.0336 0.194 Uiso 1 1 calc R U . . .
C23B C 0.7305(6) 1.1027(6) -0.01113(18) 0.1270(18) Uani 1 1 d . . . . .
C24B C 0.7891(11) 1.1845(11) -0.0037(2) 0.274(6) Uani 1 1 d . . . . .
H24B H 0.8151 1.2381 -0.0373 0.328 Uiso 1 1 calc R U . . .
C25B C 0.8129(9) 1.1930(9) 0.0524(2) 0.235(5) Uani 1 1 d . . . . .
H25B H 0.8508 1.2542 0.0559 0.281 Uiso 1 1 calc R U . . .
C26B C 0.7066(9) 1.0967(9) -0.0726(3) 0.169(3) Uani 1 1 d D . . . .
F1B F 0.9745(2) 1.1258(2) 0.36624(8) 0.0878(6) Uani 1 1 d . . . . .
N1B N 0.5288(3) 0.9754(3) 0.24587(11) 0.0746(7) Uani 1 1 d . . . . .
N2B N 0.7492(3) 1.0694(3) 0.21044(11) 0.0712(7) Uani 1 1 d . . . . .
H2B H 0.6881 1.0367 0.2033 0.085 Uiso 1 1 calc R U . . .
O1B O 0.4921(2) 0.90089(19) 0.34912(9) 0.0646(5) Uani 1 1 d . . . . .
O2B O 0.2283(2) 0.8371(2) 0.27663(10) 0.0801(6) Uani 1 1 d . . . . .
O3B O 0.3215(5) 0.6529(4) 0.2538(2) 0.1533(15) Uani 1 1 d . . . . .
O4B O 0.9015(4) 1.1806(3) 0.16309(12) 0.1234(11) Uani 1 1 d . . . . .
F2B F 0.6785(15) 1.2079(10) -0.1099(3) 0.233(4) Uani 0.619(8) 1 d D U P A 1
F3B F 0.8214(11) 1.0946(15) -0.1115(3) 0.211(4) Uani 0.619(8) 1 d D U P A 1
F4B F 0.670(2) 0.9979(12) -0.0743(4) 0.225(4) Uani 0.619(8) 1 d D U P A 1
F2D F 0.5757(19) 1.167(2) -0.0883(8) 0.234(6) Uani 0.381(8) 1 d D U P A 2
F3D F 0.806(2) 0.9988(18) -0.0924(7) 0.232(5) Uani 0.381(8) 1 d D U P A 2
F4D F 0.5724(18) 1.092(3) -0.0740(7) 0.205(5) Uani 0.381(8) 1 d D U P A 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
C1A C6A 1.382(4) . ?
C1A C2A 1.411(4) . ?
C1A C7A 1.488(4) . ?
C2A N2A 1.395(3) . ?
C2A C3A 1.398(4) . ?
C3A C4A 1.369(4) . ?
C3A H3A 0.9300 . ?
C4A F1A 1.356(3) . ?
C4A C5A 1.356(5) . ?
C5A C6A 1.379(4) . ?
C5A H5A 0.9300 . ?
C6A H6A 0.9300 . ?
C7A N1A 1.260(4) . ?
C7A O1A 1.359(3) . ?
C8A O1A 1.452(3) . ?
C8A C9A 1.499(5) . ?
C8A C11A 1.517(4) . ?
C8A H8A 0.9800 . ?
C9A O2A 1.435(4) . ?
C9A C10A 1.516(5) . ?
C9A H9A 0.9800 . ?
C10A N1A 1.459(4) . ?
C10A H10A 0.9700 . ?
C10A H10B 0.9700 . ?
C11A C16A 1.362(4) . ?
C11A C12A 1.371(5) . ?
C12A C13A 1.381(5) . ?
C12A H12A 0.9300 . ?
C13A C14A 1.358(5) . ?
C13A H13A 0.9300 . ?
C14A C15A 1.347(5) . ?
C14A H14A 0.9300 . ?
C15A C16A 1.371(5) . ?
C15A H15A 0.9300 . ?
C16A H16A 0.9300 . ?
C17A O3A 1.176(6) . ?
C17A O2A 1.321(6) . ?
C17A C18A 1.503(6) . ?
C18A H18A 0.9600 . ?
C18A H18B 0.9600 . ?
C18A H18C 0.9600 . ?
C19A O4A 1.224(3) . ?
C19A N2A 1.354(4) . ?
C19A C20A 1.491(4) . ?
C20A C21A 1.366(5) . ?
C20A C25A 1.367(4) . ?
C21A C22A 1.375(5) . ?
C21A H21A 0.9300 . ?
C22A C23A 1.367(5) . ?
C22A H22A 0.9300 . ?
C23A C24A 1.348(6) . ?
C23A C26A 1.486(7) . ?
C24A C25A 1.366(5) . ?
C24A H24A 0.9300 . ?
C25A H25A 0.9300 . ?
C26A F4A 1.233(6) . ?
C26A F2A 1.284(10) . ?
C26A F3A 1.315(9) . ?
N2A H2A 0.8600 . ?
C1B C6B 1.382(4) . ?
C1B C2B 1.421(4) . ?
C1B C7B 1.486(4) . ?
C2B N2B 1.391(4) . ?
C2B C3B 1.397(4) . ?
C3B C4B 1.355(4) . ?
C3B H3B 0.9300 . ?
C4B F1B 1.358(3) . ?
C4B C5B 1.368(4) . ?
C5B C6B 1.378(4) . ?
C5B H5B 0.9300 . ?
C6B H6B 0.9300 . ?
C7B N1B 1.259(4) . ?
C7B O1B 1.371(3) . ?
C8B O1B 1.450(3) . ?
C8B C9B 1.484(5) . ?
C8B C11B 1.511(4) . ?
C8B H8B 0.9800 . ?
C9B O2B 1.430(4) . ?
C9B C10B 1.508(5) . ?
C9B H9B 0.9800 . ?
C10B N1B 1.464(4) . ?
C10B H10C 0.9700 . ?
C10B H10D 0.9700 . ?
C11B C12B 1.364(4) . ?
C11B C16B 1.380(5) . ?
C12B C13B 1.381(5) . ?
C12B H12B 0.9300 . ?
C13B C14B 1.352(6) . ?
C13B H13B 0.9300 . ?
C14B C15B 1.357(6) . ?
C14B H14B 0.9300 . ?
C15B C16B 1.374(5) . ?
C15B H15B 0.9300 . ?
C16B H16B 0.9300 . ?
C17B O3B 1.175(5) . ?
C17B O2B 1.307(5) . ?
C17B C18B 1.488(6) . ?
C18B H18D 0.9600 . ?
C18B H18E 0.9600 . ?
C18B H18F 0.9600 . ?
C19B O4B 1.216(4) . ?
C19B N2B 1.350(4) . ?
C19B C20B 1.497(5) . ?
C20B C21B 1.315(5) . ?
C20B C25B 1.342(6) . ?
C21B C22B 1.379(6) . ?
C21B H21B 0.9300 . ?
C22B C23B 1.284(6) . ?
C22B H22B 0.9300 . ?
C23B C24B 1.318(8) . ?
C23B C26B 1.490(7) . ?
C24B C25B 1.377(8) . ?
C24B H24B 0.9300 . ?
C25B H25B 0.9300 . ?
C26B F3B 1.306(8) . ?
C26B F2D 1.318(9) . ?
C26B F4B 1.325(8) . ?
C26B F4D 1.332(9) . ?
C26B F3D 1.341(9) . ?
C26B F2B 1.345(8) . ?
N2B H2B 0.8600 . ?

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
C6A C1A C2A 118.8(3) . . ?
C6A C1A C7A 118.8(3) . . ?
C2A C1A C7A 122.4(2) . . ?
N2A C2A C3A 122.1(3) . . ?
N2A C2A C1A 118.9(2) . . ?
C3A C2A C1A 119.0(3) . . ?
C4A C3A C2A 118.8(3) . . ?
C4A C3A H3A 120.6 . . ?
C2A C3A H3A 120.6 . . ?
F1A C4A C5A 119.2(3) . . ?
F1A C4A C3A 117.0(3) . . ?
C5A C4A C3A 123.8(3) . . ?
C4A C5A C6A 117.4(3) . . ?
C4A C5A H5A 121.3 . . ?
C6A C5A H5A 121.3 . . ?
C5A C6A C1A 122.3(3) . . ?
C5A C6A H6A 118.9 . . ?
C1A C6A H6A 118.9 . . ?
N1A C7A O1A 125.8(3) . . ?
N1A C7A C1A 123.4(3) . . ?
O1A C7A C1A 110.8(2) . . ?
O1A C8A C9A 107.5(2) . . ?
O1A C8A C11A 106.1(2) . . ?
C9A C8A C11A 116.0(3) . . ?
O1A C8A H8A 109.1 . . ?
C9A C8A H8A 109.1 . . ?
C11A C8A H8A 109.1 . . ?
O2A C9A C8A 107.0(3) . . ?
O2A C9A C10A 108.7(3) . . ?
C8A C9A C10A 109.7(3) . . ?
O2A C9A H9A 110.5 . . ?
C8A C9A H9A 110.5 . . ?
C10A C9A H9A 110.5 . . ?
N1A C10A C9A 113.9(3) . . ?
N1A C10A H10A 108.8 . . ?
C9A C10A H10A 108.8 . . ?
N1A C10A H10B 108.8 . . ?
C9A C10A H10B 108.8 . . ?
H10A C10A H10B 107.7 . . ?
C16A C11A C12A 118.0(3) . . ?
C16A C11A C8A 120.0(3) . . ?
C12A C11A C8A 121.9(3) . . ?
C11A C12A C13A 120.8(3) . . ?
C11A C12A H12A 119.6 . . ?
C13A C12A H12A 119.6 . . ?
C14A C13A C12A 119.8(4) . . ?
C14A C13A H13A 120.1 . . ?
C12A C13A H13A 120.1 . . ?
C15A C14A C13A 119.8(4) . . ?
C15A C14A H14A 120.1 . . ?
C13A C14A H14A 120.1 . . ?
C14A C15A C16A 120.5(4) . . ?
C14A C15A H15A 119.7 . . ?
C16A C15A H15A 119.7 . . ?
C11A C16A C15A 121.0(3) . . ?
C11A C16A H16A 119.5 . . ?
C15A C16A H16A 119.5 . . ?
O3A C17A O2A 122.6(4) . . ?
O3A C17A C18A 126.0(5) . . ?
O2A C17A C18A 111.4(5) . . ?
C17A C18A H18A 109.5 . . ?
C17A C18A H18B 109.5 . . ?
H18A C18A H18B 109.5 . . ?
C17A C18A H18C 109.5 . . ?
H18A C18A H18C 109.5 . . ?
H18B C18A H18C 109.5 . . ?
O4A C19A N2A 123.8(3) . . ?
O4A C19A C20A 120.4(3) . . ?
N2A C19A C20A 115.9(3) . . ?
C21A C20A C25A 117.2(3) . . ?
C21A C20A C19A 124.6(3) . . ?
C25A C20A C19A 118.1(3) . . ?
C20A C21A C22A 121.3(3) . . ?
C20A C21A H21A 119.3 . . ?
C22A C21A H21A 119.3 . . ?
C23A C22A C21A 119.9(4) . . ?
C23A C22A H22A 120.1 . . ?
C21A C22A H22A 120.1 . . ?
C24A C23A C22A 119.5(4) . . ?
C24A C23A C26A 121.8(4) . . ?
C22A C23A C26A 118.7(4) . . ?
C23A C24A C25A 120.1(3) . . ?
C23A C24A H24A 119.9 . . ?
C25A C24A H24A 119.9 . . ?
C24A C25A C20A 121.9(3) . . ?
C24A C25A H25A 119.0 . . ?
C20A C25A H25A 119.0 . . ?
F4A C26A F2A 106.1(8) . . ?
F4A C26A F3A 105.7(8) . . ?
F2A C26A F3A 100.6(5) . . ?
F4A C26A C23A 118.5(5) . . ?
F2A C26A C23A 113.0(7) . . ?
F3A C26A C23A 111.2(7) . . ?
C7A N1A C10A 120.0(3) . . ?
C19A N2A C2A 129.2(2) . . ?
C19A N2A H2A 115.4 . . ?
C2A N2A H2A 115.4 . . ?
C7A O1A C8A 117.1(2) . . ?
C17A O2A C9A 117.3(3) . . ?
C6B C1B C2B 118.0(3) . . ?
C6B C1B C7B 119.4(2) . . ?
C2B C1B C7B 122.6(3) . . ?
N2B C2B C3B 122.2(2) . . ?
N2B C2B C1B 118.8(3) . . ?
C3B C2B C1B 119.0(3) . . ?
C4B C3B C2B 119.3(3) . . ?
C4B C3B H3B 120.3 . . ?
C2B C3B H3B 120.3 . . ?
C3B C4B F1B 118.0(3) . . ?
C3B C4B C5B 123.7(3) . . ?
F1B C4B C5B 118.3(3) . . ?
C4B C5B C6B 117.0(3) . . ?
C4B C5B H5B 121.5 . . ?
C6B C5B H5B 121.5 . . ?
C5B C6B C1B 122.9(3) . . ?
C5B C6B H6B 118.5 . . ?
C1B C6B H6B 118.5 . . ?
N1B C7B O1B 125.4(3) . . ?
N1B C7B C1B 123.0(3) . . ?
O1B C7B C1B 111.5(2) . . ?
O1B C8B C9B 108.9(2) . . ?
O1B C8B C11B 108.2(2) . . ?
C9B C8B C11B 116.2(3) . . ?
O1B C8B H8B 107.7 . . ?
C9B C8B H8B 107.7 . . ?
C11B C8B H8B 107.7 . . ?
O2B C9B C8B 107.9(3) . . ?
O2B C9B C10B 109.6(3) . . ?
C8B C9B C10B 110.6(3) . . ?
O2B C9B H9B 109.6 . . ?
C8B C9B H9B 109.6 . . ?
C10B C9B H9B 109.6 . . ?
N1B C10B C9B 113.3(3) . . ?
N1B C10B H10C 108.9 . . ?
C9B C10B H10C 108.9 . . ?
N1B C10B H10D 108.9 . . ?
C9B C10B H10D 108.9 . . ?
H10C C10B H10D 107.7 . . ?
C12B C11B C16B 117.4(3) . . ?
C12B C11B C8B 119.1(3) . . ?
C16B C11B C8B 123.5(3) . . ?
C11B C12B C13B 121.1(4) . . ?
C11B C12B H12B 119.5 . . ?
C13B C12B H12B 119.5 . . ?
C14B C13B C12B 120.5(4) . . ?
C14B C13B H13B 119.7 . . ?
C12B C13B H13B 119.7 . . ?
C13B C14B C15B 119.6(4) . . ?
C13B C14B H14B 120.2 . . ?
C15B C14B H14B 120.2 . . ?
C14B C15B C16B 120.0(4) . . ?
C14B C15B H15B 120.0 . . ?
C16B C15B H15B 120.0 . . ?
C15B C16B C11B 121.4(4) . . ?
C15B C16B H16B 119.3 . . ?
C11B C16B H16B 119.3 . . ?
O3B C17B O2B 123.3(4) . . ?
O3B C17B C18B 125.3(4) . . ?
O2B C17B C18B 111.4(5) . . ?
C17B C18B H18D 109.5 . . ?
C17B C18B H18E 109.5 . . ?
H18D C18B H18E 109.5 . . ?
C17B C18B H18F 109.5 . . ?
H18D C18B H18F 109.5 . . ?
H18E C18B H18F 109.5 . . ?
O4B C19B N2B 124.3(3) . . ?
O4B C19B C20B 120.0(3) . . ?
N2B C19B C20B 115.6(3) . . ?
C21B C20B C25B 115.0(4) . . ?
C21B C20B C19B 126.0(3) . . ?
C25B C20B C19B 118.8(4) . . ?
C20B C21B C22B 122.1(4) . . ?
C20B C21B H21B 118.9 . . ?
C22B C21B H21B 118.9 . . ?
C23B C22B C21B 122.7(5) . . ?
C23B C22B H22B 118.7 . . ?
C21B C22B H22B 118.7 . . ?
C22B C23B C24B 116.3(5) . . ?
C22B C23B C26B 123.3(5) . . ?
C24B C23B C26B 120.2(5) . . ?
C23B C24B C25B 122.0(5) . . ?
C23B C24B H24B 119.0 . . ?
C25B C24B H24B 119.0 . . ?
C20B C25B C24B 121.2(6) . . ?
C20B C25B H25B 119.4 . . ?
C24B C25B H25B 119.4 . . ?
F3B C26B F4B 106.0(10) . . ?
F2D C26B F4D 38.3(14) . . ?
F2D C26B F3D 132.7(13) . . ?
F4D C26B F3D 109.3(14) . . ?
F3B C26B F2B 72.5(8) . . ?
F4B C26B F2B 129.8(10) . . ?
F3B C26B C23B 113.4(6) . . ?
F2D C26B C23B 112.8(10) . . ?
F4B C26B C23B 113.3(7) . . ?
F4D C26B C23B 111.1(9) . . ?
F3D C26B C23B 111.7(9) . . ?
F2B C26B C23B 112.6(6) . . ?
C7B N1B C10B 121.0(3) . . ?
C19B N2B C2B 129.1(3) . . ?
C19B N2B H2B 115.4 . . ?
C2B N2B H2B 115.4 . . ?
C7B O1B C8B 115.9(2) . . ?
C17B O2B C9B 119.4(3) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6A C1A C2A N2A -179.1(3) . . . . ?
C7A C1A C2A N2A 2.7(4) . . . . ?
C6A C1A C2A C3A 0.8(4) . . . . ?
C7A C1A C2A C3A -177.5(3) . . . . ?
N2A C2A C3A C4A 179.3(3) . . . . ?
C1A C2A C3A C4A -0.6(4) . . . . ?
C2A C3A C4A F1A 180.0(3) . . . . ?
C2A C3A C4A C5A 0.3(5) . . . . ?
F1A C4A C5A C6A -179.9(3) . . . . ?
C3A C4A C5A C6A -0.2(5) . . . . ?
C4A C5A C6A C1A 0.4(5) . . . . ?
C2A C1A C6A C5A -0.7(5) . . . . ?
C7A C1A C6A C5A 177.6(3) . . . . ?
C6A C1A C7A N1A -176.9(3) . . . . ?
C2A C1A C7A N1A 1.4(5) . . . . ?
C6A C1A C7A O1A 4.2(4) . . . . ?
C2A C1A C7A O1A -177.5(2) . . . . ?
O1A C8A C9A O2A 174.7(3) . . . . ?
C11A C8A C9A O2A -66.9(4) . . . . ?
O1A C8A C9A C10A 56.9(4) . . . . ?
C11A C8A C9A C10A 175.3(3) . . . . ?
O2A C9A C10A N1A -158.5(3) . . . . ?
C8A C9A C10A N1A -41.8(4) . . . . ?
O1A C8A C11A C16A -119.0(3) . . . . ?
C9A C8A C11A C16A 121.8(4) . . . . ?
O1A C8A C11A C12A 57.4(4) . . . . ?
C9A C8A C11A C12A -61.8(4) . . . . ?
C16A C11A C12A C13A 1.4(5) . . . . ?
C8A C11A C12A C13A -175.1(3) . . . . ?
C11A C12A C13A C14A -1.6(6) . . . . ?
C12A C13A C14A C15A 0.8(7) . . . . ?
C13A C14A C15A C16A 0.2(7) . . . . ?
C12A C11A C16A C15A -0.4(6) . . . . ?
C8A C11A C16A C15A 176.2(4) . . . . ?
C14A C15A C16A C11A -0.4(7) . . . . ?
O4A C19A C20A C21A 175.3(4) . . . . ?
N2A C19A C20A C21A -5.1(6) . . . . ?
O4A C19A C20A C25A -4.2(5) . . . . ?
N2A C19A C20A C25A 175.5(3) . . . . ?
C25A C20A C21A C22A -0.5(8) . . . . ?
C19A C20A C21A C22A -179.9(5) . . . . ?
C20A C21A C22A C23A 0.7(10) . . . . ?
C21A C22A C23A C24A -0.7(9) . . . . ?
C21A C22A C23A C26A 179.8(7) . . . . ?
C22A C23A C24A C25A 0.5(8) . . . . ?
C26A C23A C24A C25A 179.9(7) . . . . ?
C23A C24A C25A C20A -0.2(8) . . . . ?
C21A C20A C25A C24A 0.2(7) . . . . ?
C19A C20A C25A C24A 179.7(4) . . . . ?
C24A C23A C26A F4A 171.9(8) . . . . ?
C22A C23A C26A F4A -8.6(13) . . . . ?
C24A C23A C26A F2A -63.1(11) . . . . ?
C22A C23A C26A F2A 116.3(8) . . . . ?
C24A C23A C26A F3A 49.2(11) . . . . ?
C22A C23A C26A F3A -131.4(7) . . . . ?
O1A C7A N1A C10A 1.7(5) . . . . ?
C1A C7A N1A C10A -177.0(3) . . . . ?
C9A C10A N1A C7A 12.1(5) . . . . ?
O4A C19A N2A C2A 0.8(5) . . . . ?
C20A C19A N2A C2A -178.9(3) . . . . ?
C3A C2A N2A C19A -1.5(5) . . . . ?
C1A C2A N2A C19A 178.4(3) . . . . ?
N1A C7A O1A C8A 16.8(5) . . . . ?
C1A C7A O1A C8A -164.3(2) . . . . ?
C9A C8A O1A C7A -46.0(4) . . . . ?
C11A C8A O1A C7A -170.6(2) . . . . ?
O3A C17A O2A C9A -6.8(7) . . . . ?
C18A C17A O2A C9A 172.9(3) . . . . ?
C8A C9A O2A C17A 143.7(3) . . . . ?
C10A C9A O2A C17A -97.9(4) . . . . ?
C6B C1B C2B N2B 179.2(3) . . . . ?
C7B C1B C2B N2B -1.2(4) . . . . ?
C6B C1B C2B C3B -0.2(4) . . . . ?
C7B C1B C2B C3B 179.3(3) . . . . ?
N2B C2B C3B C4B 179.9(3) . . . . ?
C1B C2B C3B C4B -0.7(5) . . . . ?
C2B C3B C4B F1B -178.4(3) . . . . ?
C2B C3B C4B C5B 2.0(5) . . . . ?
C3B C4B C5B C6B -2.1(5) . . . . ?
F1B C4B C5B C6B 178.3(3) . . . . ?
C4B C5B C6B C1B 1.1(5) . . . . ?
C2B C1B C6B C5B 0.1(4) . . . . ?
C7B C1B C6B C5B -179.5(3) . . . . ?
C6B C1B C7B N1B 174.7(3) . . . . ?
C2B C1B C7B N1B -4.8(5) . . . . ?
C6B C1B C7B O1B -5.3(4) . . . . ?
C2B C1B C7B O1B 175.1(2) . . . . ?
O1B C8B C9B O2B -176.2(2) . . . . ?
C11B C8B C9B O2B 61.4(4) . . . . ?
O1B C8B C9B C10B -56.4(4) . . . . ?
C11B C8B C9B C10B -178.8(3) . . . . ?
O2B C9B C10B N1B 158.6(3) . . . . ?
C8B C9B C10B N1B 39.7(4) . . . . ?
O1B C8B C11B C12B 103.0(3) . . . . ?
C9B C8B C11B C12B -134.2(3) . . . . ?
O1B C8B C11B C16B -78.5(4) . . . . ?
C9B C8B C11B C16B 44.3(4) . . . . ?
C16B C11B C12B C13B -0.2(5) . . . . ?
C8B C11B C12B C13B 178.4(3) . . . . ?
C11B C12B C13B C14B 1.0(6) . . . . ?
C12B C13B C14B C15B -0.9(6) . . . . ?
C13B C14B C15B C16B 0.0(6) . . . . ?
C14B C15B C16B C11B 0.8(6) . . . . ?
C12B C11B C16B C15B -0.7(5) . . . . ?
C8B C11B C16B C15B -179.2(3) . . . . ?
O4B C19B C20B C21B 168.7(5) . . . . ?
N2B C19B C20B C21B -11.8(7) . . . . ?
O4B C19B C20B C25B -17.2(8) . . . . ?
N2B C19B C20B C25B 162.4(6) . . . . ?
C25B C20B C21B C22B 6.7(10) . . . . ?
C19B C20B C21B C22B -179.0(6) . . . . ?
C20B C21B C22B C23B 0.6(11) . . . . ?
C21B C22B C23B C24B -6.5(12) . . . . ?
C21B C22B C23B C26B 178.6(7) . . . . ?
C22B C23B C24B C25B 4.9(15) . . . . ?
C26B C23B C24B C25B 180.0(9) . . . . ?
C21B C20B C25B C24B -8.1(13) . . . . ?
C19B C20B C25B C24B 177.1(8) . . . . ?
C23B C24B C25B C20B 2.6(17) . . . . ?
C22B C23B C26B F3B -136.7(11) . . . . ?
C24B C23B C26B F3B 48.6(14) . . . . ?
C22B C23B C26B F2D 83.1(17) . . . . ?
C24B C23B C26B F2D -91.6(16) . . . . ?
C22B C23B C26B F4B -15.7(16) . . . . ?
C24B C23B C26B F4B 169.6(13) . . . . ?
C22B C23B C26B F4D 42(2) . . . . ?
C24B C23B C26B F4D -132.9(18) . . . . ?
C22B C23B C26B F3D -80.6(14) . . . . ?
C24B C23B C26B F3D 104.7(15) . . . . ?
C22B C23B C26B F2B 143.4(9) . . . . ?
C24B C23B C26B F2B -31.3(12) . . . . ?
O1B C7B N1B C10B -1.4(5) . . . . ?
C1B C7B N1B C10B 178.6(3) . . . . ?
C9B C10B N1B C7B -10.7(5) . . . . ?
O4B C19B N2B C2B -3.7(7) . . . . ?
C20B C19B N2B C2B 176.8(3) . . . . ?
C3B C2B N2B C19B -5.1(5) . . . . ?
C1B C2B N2B C19B 175.5(3) . . . . ?
N1B C7B O1B C8B -17.4(4) . . . . ?
C1B C7B O1B C8B 162.7(2) . . . . ?
C9B C8B O1B C7B 46.0(4) . . . . ?
C11B C8B O1B C7B 173.1(2) . . . . ?
O3B C17B O2B C9B 0.2(6) . . . . ?
C18B C17B O2B C9B -179.5(3) . . . . ?
C8B C9B O2B C17B -134.3(3) . . . . ?
C10B C9B O2B C17B 105.2(4) . . . . ?

_refine_diff_density_max         0.515
_refine_diff_density_min         -0.468
_refine_diff_density_rms         0.079

####################################################################### 
# 
# 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_KA08_0m_a
_database_code_depnum_ccdc_archive 'CCDC 1505773'
_audit_update_record             
;
2016-09-22 deposited with the CCDC.
2016-10-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
'(2-(2-Benzamidophenyl)-4,5-dihydrooxazol-5-yl)methyl acetate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H18 N2 O4'
_chemical_formula_sum            'C19 H18 N2 O4'
_chemical_formula_weight         338.35

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_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'
'-x, -y, -z'

_cell_length_a                   7.3604(4)
_cell_length_b                   9.3854(6)
_cell_length_c                   12.8395(10)
_cell_angle_alpha                95.461(4)
_cell_angle_beta                 101.655(4)
_cell_angle_gamma                105.055(3)
_cell_volume                     828.57(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    99(2)
_cell_measurement_reflns_used    4320
_cell_measurement_theta_min      2.27
_cell_measurement_theta_max      24.84

_exptl_crystal_description       needle
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.356
_exptl_crystal_F_000             356
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.070
_exptl_absorpt_coefficient_mu    0.096
_shelx_estimated_absorpt_T_min   0.987
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.92
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_process_details   'SADABS; Bruker,2016'

_diffrn_ambient_temperature      99(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON-100'
_diffrn_measurement_method       'ω and φ'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10690
_diffrn_reflns_av_unetI/netI     0.0966
_diffrn_reflns_av_R_equivalents  0.0775
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.589
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_full        24.999
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             2911
_reflns_number_gt                1695
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       'APEX3 (Bruker, 2016)'
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL2014 (Sheldrick, 2015b)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0516P)²+1.2525P] 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_number_reflns         2911
_refine_ls_number_parameters     232
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1379
_refine_ls_R_factor_gt           0.0723
_refine_ls_wR_factor_ref         0.1703
_refine_ls_wR_factor_gt          0.1438
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.029
_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
C1 C 0.8163(5) 0.4993(4) 0.3451(3) 0.0203(9) Uani 1 1 d . . . . .
C2 C 0.8379(5) 0.6322(4) 0.4140(3) 0.0202(9) Uani 1 1 d . . . . .
C3 C 0.9007(5) 0.7695(4) 0.3801(3) 0.0247(10) Uani 1 1 d . . . . .
H3 H 0.9123 0.8594 0.4251 0.030 Uiso 1 1 calc R U . . .
C4 C 0.9462(6) 0.7745(4) 0.2811(3) 0.0272(10) Uani 1 1 d . . . . .
H4 H 0.9901 0.8686 0.2589 0.033 Uiso 1 1 calc R U . . .
C5 C 0.9291(5) 0.6458(4) 0.2136(3) 0.0272(10) Uani 1 1 d . . . . .
H5 H 0.9618 0.6510 0.1459 0.033 Uiso 1 1 calc R U . . .
C6 C 0.8640(5) 0.5095(4) 0.2459(3) 0.0247(9) Uani 1 1 d . . . . .
H6 H 0.8513 0.4207 0.1995 0.030 Uiso 1 1 calc R U . . .
C7 C 0.7445(5) 0.3510(4) 0.3742(3) 0.0220(9) Uani 1 1 d . . . . .
C8 C 0.6633(6) 0.0977(4) 0.3479(3) 0.0354(11) Uani 1 1 d . . . . .
H8 H 0.7665 0.0455 0.3605 0.043 Uiso 1 1 calc R U . . .
C10 C 0.4868(7) -0.0015(5) 0.2763(3) 0.0415(12) Uani 1 1 d . . . . .
H10A H 0.3923 0.0548 0.2550 0.050 Uiso 1 1 calc R U . . .
H10B H 0.4275 -0.0828 0.3134 0.050 Uiso 1 1 calc R U . . .
C9 C 0.6318(6) 0.1592(4) 0.4550(3) 0.0275(10) Uani 1 1 d . . . . .
H9A H 0.4935 0.1248 0.4565 0.033 Uiso 1 1 calc R U . . .
H9B H 0.7093 0.1269 0.5157 0.033 Uiso 1 1 calc R U . . .
C11 C 0.3850(9) -0.1249(5) 0.0972(4) 0.0472(13) Uani 1 1 d . . . . .
C12 C 0.4431(9) -0.1912(5) 0.0028(4) 0.0681(18) Uani 1 1 d . . . . .
H12A H 0.4136 -0.2997 0.0002 0.102 Uiso 1 1 calc R U . . .
H12B H 0.5824 -0.1484 0.0102 0.102 Uiso 1 1 calc R U . . .
H12C H 0.3715 -0.1690 -0.0637 0.102 Uiso 1 1 calc R U . . .
C13 C 0.8157(5) 0.7281(4) 0.5986(3) 0.0221(9) Uani 1 1 d . . . . .
C14 C 0.7779(5) 0.6720(4) 0.6991(3) 0.0244(9) Uani 1 1 d . . . . .
C15 C 0.6586(5) 0.5311(4) 0.7004(3) 0.0240(9) Uani 1 1 d . . . . .
H15 H 0.5967 0.4655 0.6345 0.029 Uiso 1 1 calc R U . . .
C16 C 0.6284(6) 0.4847(4) 0.7958(3) 0.0298(10) Uani 1 1 d . . . . .
H16 H 0.5438 0.3888 0.7951 0.036 Uiso 1 1 calc R U . . .
C17 C 0.7215(6) 0.5778(5) 0.8926(3) 0.0346(10) Uani 1 1 d . . . . .
H17 H 0.7035 0.5451 0.9586 0.042 Uiso 1 1 calc R U . . .
C18 C 0.8411(6) 0.7191(5) 0.8929(3) 0.0351(11) Uani 1 1 d . . . . .
H18 H 0.9049 0.7834 0.9592 0.042 Uiso 1 1 calc R U . . .
C19 C 0.8677(6) 0.7664(4) 0.7967(3) 0.0292(10) Uani 1 1 d . . . . .
H19 H 0.9477 0.8640 0.7973 0.035 Uiso 1 1 calc R U . . .
N1 N 0.6960(4) 0.3222(3) 0.4613(3) 0.0243(8) Uani 1 1 d . . . . .
N2 N 0.7971(5) 0.6193(4) 0.5161(3) 0.0228(8) Uani 1 1 d . . . . .
H2N H 0.760(5) 0.532(4) 0.526(3) 0.022(11) Uiso 1 1 d . . . . .
O1 O 0.7287(4) 0.2326(3) 0.2995(2) 0.0335(7) Uani 1 1 d . . . . .
O2 O 0.5380(5) -0.0644(3) 0.1804(2) 0.0425(8) Uani 1 1 d . . . . .
O3 O 0.2226(6) -0.1238(4) 0.0992(3) 0.0740(13) Uani 1 1 d . . . . .
O4 O 0.8629(4) 0.8625(3) 0.5936(2) 0.0310(7) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.393(5) . ?
C1 C2 1.413(5) . ?
C1 C7 1.467(5) . ?
C2 C3 1.393(5) . ?
C2 N2 1.411(5) . ?
C3 C4 1.381(5) . ?
C3 H3 0.9500 . ?
C4 C5 1.380(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.379(5) . ?
C5 H5 0.9500 . ?
C6 H6 0.9500 . ?
C7 N1 1.273(5) . ?
C7 O1 1.361(4) . ?
C8 C10 1.458(6) . ?
C8 O1 1.475(5) . ?
C8 C9 1.524(5) . ?
C8 H8 1.0000 . ?
C10 O2 1.474(5) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C9 N1 1.468(4) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C11 O3 1.203(6) . ?
C11 O2 1.341(6) . ?
C11 C12 1.498(7) . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 O4 1.229(4) . ?
C13 N2 1.360(5) . ?
C13 C14 1.489(6) . ?
C14 C15 1.388(5) . ?
C14 C19 1.394(5) . ?
C15 C16 1.378(5) . ?
C15 H15 0.9500 . ?
C16 C17 1.385(5) . ?
C16 H16 0.9500 . ?
C17 C18 1.387(6) . ?
C17 H17 0.9500 . ?
C18 C19 1.385(6) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?
N2 H2N 0.83(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 C1 C2 118.8(3) . . ?
C6 C1 C7 119.0(3) . . ?
C2 C1 C7 122.2(3) . . ?
C3 C2 N2 122.8(3) . . ?
C3 C2 C1 119.4(4) . . ?
N2 C2 C1 117.8(3) . . ?
C4 C3 C2 119.9(3) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C5 C4 C3 121.4(4) . . ?
C5 C4 H4 119.3 . . ?
C3 C4 H4 119.3 . . ?
C6 C5 C4 119.0(4) . . ?
C6 C5 H5 120.5 . . ?
C4 C5 H5 120.5 . . ?
C5 C6 C1 121.5(4) . . ?
C5 C6 H6 119.3 . . ?
C1 C6 H6 119.3 . . ?
N1 C7 O1 117.2(3) . . ?
N1 C7 C1 126.9(3) . . ?
O1 C7 C1 115.9(3) . . ?
C10 C8 O1 109.2(4) . . ?
C10 C8 C9 113.1(4) . . ?
O1 C8 C9 103.5(3) . . ?
C10 C8 H8 110.3 . . ?
O1 C8 H8 110.3 . . ?
C9 C8 H8 110.3 . . ?
C8 C10 O2 108.2(4) . . ?
C8 C10 H10A 110.1 . . ?
O2 C10 H10A 110.1 . . ?
C8 C10 H10B 110.1 . . ?
O2 C10 H10B 110.1 . . ?
H10A C10 H10B 108.4 . . ?
N1 C9 C8 104.9(3) . . ?
N1 C9 H9A 110.8 . . ?
C8 C9 H9A 110.8 . . ?
N1 C9 H9B 110.8 . . ?
C8 C9 H9B 110.8 . . ?
H9A C9 H9B 108.8 . . ?
O3 C11 O2 123.5(5) . . ?
O3 C11 C12 125.0(5) . . ?
O2 C11 C12 111.4(5) . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O4 C13 N2 124.1(4) . . ?
O4 C13 C14 121.5(3) . . ?
N2 C13 C14 114.4(3) . . ?
C15 C14 C19 118.6(4) . . ?
C15 C14 C13 123.5(3) . . ?
C19 C14 C13 118.0(3) . . ?
C16 C15 C14 121.1(4) . . ?
C16 C15 H15 119.4 . . ?
C14 C15 H15 119.4 . . ?
C15 C16 C17 120.0(4) . . ?
C15 C16 H16 120.0 . . ?
C17 C16 H16 120.0 . . ?
C16 C17 C18 119.7(4) . . ?
C16 C17 H17 120.1 . . ?
C18 C17 H17 120.1 . . ?
C19 C18 C17 120.1(4) . . ?
C19 C18 H18 119.9 . . ?
C17 C18 H18 119.9 . . ?
C18 C19 C14 120.5(4) . . ?
C18 C19 H19 119.8 . . ?
C14 C19 H19 119.8 . . ?
C7 N1 C9 108.0(3) . . ?
C13 N2 C2 129.5(3) . . ?
C13 N2 H2N 117(3) . . ?
C2 N2 H2N 113(3) . . ?
C7 O1 C8 106.3(3) . . ?
C11 O2 C10 113.3(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
C6 C1 C2 C3 1.8(5) . . . . ?
C7 C1 C2 C3 -177.9(3) . . . . ?
C6 C1 C2 N2 -177.2(3) . . . . ?
C7 C1 C2 N2 3.2(5) . . . . ?
N2 C2 C3 C4 177.2(3) . . . . ?
C1 C2 C3 C4 -1.7(5) . . . . ?
C2 C3 C4 C5 0.6(6) . . . . ?
C3 C4 C5 C6 0.5(6) . . . . ?
C4 C5 C6 C1 -0.4(6) . . . . ?
C2 C1 C6 C5 -0.7(5) . . . . ?
C7 C1 C6 C5 178.9(3) . . . . ?
C6 C1 C7 N1 179.5(4) . . . . ?
C2 C1 C7 N1 -0.8(6) . . . . ?
C6 C1 C7 O1 -0.5(5) . . . . ?
C2 C1 C7 O1 179.2(3) . . . . ?
O1 C8 C10 O2 70.5(4) . . . . ?
C9 C8 C10 O2 -174.9(3) . . . . ?
C10 C8 C9 N1 -122.3(4) . . . . ?
O1 C8 C9 N1 -4.3(4) . . . . ?
O4 C13 C14 C15 154.7(4) . . . . ?
N2 C13 C14 C15 -26.6(5) . . . . ?
O4 C13 C14 C19 -25.3(5) . . . . ?
N2 C13 C14 C19 153.4(3) . . . . ?
C19 C14 C15 C16 0.1(5) . . . . ?
C13 C14 C15 C16 -179.9(4) . . . . ?
C14 C15 C16 C17 -1.6(6) . . . . ?
C15 C16 C17 C18 1.6(6) . . . . ?
C16 C17 C18 C19 -0.2(6) . . . . ?
C17 C18 C19 C14 -1.2(6) . . . . ?
C15 C14 C19 C18 1.3(6) . . . . ?
C13 C14 C19 C18 -178.7(4) . . . . ?
O1 C7 N1 C9 -0.4(4) . . . . ?
C1 C7 N1 C9 179.6(3) . . . . ?
C8 C9 N1 C7 3.1(4) . . . . ?
O4 C13 N2 C2 4.8(6) . . . . ?
C14 C13 N2 C2 -173.9(3) . . . . ?
C3 C2 N2 C13 -2.7(6) . . . . ?
C1 C2 N2 C13 176.2(3) . . . . ?
N1 C7 O1 C8 -2.5(4) . . . . ?
C1 C7 O1 C8 177.5(3) . . . . ?
C10 C8 O1 C7 124.8(4) . . . . ?
C9 C8 O1 C7 4.1(4) . . . . ?
O3 C11 O2 C10 2.3(6) . . . . ?
C12 C11 O2 C10 -178.3(3) . . . . ?
C8 C10 O2 C11 -163.4(4) . . . . ?

_refine_diff_density_max         0.636
_refine_diff_density_min         -0.299
_refine_diff_density_rms         0.066

