# Electronic Supplementary Material (ESI) for Chemical Communications.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_platon
_database_code_depnum_ccdc_archive 'CCDC 1866300'
_audit_update_record             
;
2018-11-14 deposited with the CCDC.
2018-11-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        unk
_chemical_name_common            ?
_chemical_formula_moiety         'C16 H12 N2 O5, C6 H15 N'
_chemical_formula_sum            'C22 H27 N3 O5'
_exptl_crystal_recrystallization_method methanol
_chemical_melting_point          ?

_exptl_crystal_description       needle
_exptl_crystal_colour            orange

_diffrn_ambient_temperature      293(2)
_chemical_formula_weight         413.47

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_int_tables_number      14
_chemical_absolute_configuration ?

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

_cell_length_a                   19.306(3)
_cell_length_b                   10.033(2)
_cell_length_c                   11.1506(14)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.091(13)
_cell_angle_gamma                90.00
_cell_volume                     2156.7(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    25860
_cell_measurement_theta_min      2.89
_cell_measurement_theta_max      25.00
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.25
_exptl_crystal_size_min          0.22
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.273
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             880
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.975
_exptl_absorpt_correction_T_max  0.980
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            15507
_diffrn_reflns_av_R_equivalents  0.1143
_diffrn_reflns_av_sigmaI/netI    0.1230
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.89
_diffrn_reflns_theta_max         25.00
_reflns_number_total             3762
_reflns_number_gt                2070
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.2000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     SHELXL
_refine_ls_extinction_coef       0.016(9)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3762
_refine_ls_number_parameters     276
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2791
_refine_ls_R_factor_gt           0.2241
_refine_ls_wR_factor_ref         0.5529
_refine_ls_wR_factor_gt          0.5229
_refine_ls_goodness_of_fit_ref   1.741
_refine_ls_restrained_S_all      1.741
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O4 O 0.1550(4) 0.5594(8) -0.0341(5) 0.047(2) Uani 1 1 d . . .
O2 O 0.5674(5) 0.6262(12) 0.1068(10) 0.099(4) Uani 1 1 d . . .
O1 O 0.5762(5) 0.7898(11) 0.2353(10) 0.093(3) Uani 1 1 d . . .
O3 O 0.1664(4) 0.4846(7) 0.3281(5) 0.046(2) Uani 1 1 d . . .
H3A H 0.1968 0.5285 0.3641 0.069 Uiso 1 1 calc R . .
O5 O 0.2348(4) 0.7167(7) -0.0145(6) 0.051(2) Uani 1 1 d . . .
N2 N 0.2558(4) 0.6775(8) 0.2351(7) 0.043(2) Uani 1 1 d . . .
H2 H 0.2406 0.7226 0.2936 0.052 Uiso 1 1 calc R . .
N1 N 0.5425(6) 0.7046(12) 0.1779(10) 0.069(3) Uani 1 1 d . . .
C7 C 0.2066(5) 0.6032(9) 0.1620(7) 0.031(2) Uani 1 1 d . . .
C13 C 0.0190(5) 0.2833(11) 0.1014(9) 0.048(3) Uani 1 1 d . . .
C11 C 0.2008(5) 0.6326(10) 0.0384(8) 0.036(2) Uani 1 1 d . . .
C10 C 0.1112(5) 0.4676(10) 0.0119(8) 0.039(2) Uani 1 1 d . . .
C15 C 0.0660(6) 0.4005(12) -0.0661(9) 0.051(3) Uani 1 1 d . . .
H15 H 0.0664 0.4165 -0.1482 0.061 Uiso 1 1 calc R . .
C14 C 0.0199(6) 0.3089(11) -0.0223(8) 0.049(3) Uani 1 1 d . . .
H14 H -0.0107 0.2639 -0.0753 0.059 Uiso 1 1 calc R . .
C12 C 0.0653(5) 0.3501(11) 0.1793(8) 0.045(3) Uani 1 1 d . . .
H12 H 0.0650 0.3338 0.2614 0.054 Uiso 1 1 calc R . .
C9 C 0.1125(5) 0.4418(9) 0.1363(7) 0.034(2) Uani 1 1 d . . .
C8 C 0.1653(5) 0.5129(10) 0.2161(8) 0.038(2) Uani 1 1 d . . .
C4 C 0.3249(5) 0.6820(10) 0.2189(8) 0.042(3) Uani 1 1 d . . .
C3 C 0.3687(6) 0.7669(10) 0.2929(9) 0.045(3) Uani 1 1 d . . .
H3 H 0.3494 0.8178 0.3523 0.054 Uiso 1 1 calc R . .
C2 C 0.4390(6) 0.7747(12) 0.2778(10) 0.057(3) Uani 1 1 d . . .
H2A H 0.4665 0.8333 0.3241 0.069 Uiso 1 1 calc R . .
C1 C 0.4683(6) 0.6951(12) 0.1937(10) 0.053(3) Uani 1 1 d . . .
C6 C 0.4286(6) 0.6074(12) 0.1234(9) 0.056(3) Uani 1 1 d . . .
H6 H 0.4493 0.5532 0.0680 0.067 Uiso 1 1 calc R . .
C5 C 0.3584(6) 0.6010(11) 0.1361(9) 0.047(3) Uani 1 1 d . . .
H5 H 0.3321 0.5414 0.0888 0.056 Uiso 1 1 calc R . .
C16 C -0.0329(7) 0.1842(14) 0.1438(10) 0.075(4) Uani 1 1 d . . .
H16A H -0.0417 0.2019 0.2262 0.113 Uiso 1 1 calc R . .
H16B H -0.0147 0.0956 0.1368 0.113 Uiso 1 1 calc R . .
H16C H -0.0754 0.1919 0.0954 0.113 Uiso 1 1 calc R . .
N3 N 0.2614(5) 0.0707(9) 0.0101(7) 0.047(2) Uani 1 1 d . . .
C17 C 0.1649(9) -0.0011(16) 0.1363(12) 0.088(5) Uani 1 1 d . . .
H17A H 0.1438 0.0759 0.0986 0.132 Uiso 1 1 calc R . .
H17B H 0.1567 -0.0005 0.2204 0.132 Uiso 1 1 calc R . .
H17C H 0.1453 -0.0803 0.1001 0.132 Uiso 1 1 calc R . .
C18 C 0.2434(8) 0.0014(12) 0.1197(9) 0.067(4) Uani 1 1 d . . .
H18A H 0.2665 0.0451 0.1885 0.081 Uiso 1 1 calc R . .
H18B H 0.2605 -0.0895 0.1172 0.081 Uiso 1 1 calc R . .
C22 C 0.3305(6) 0.0226(13) -0.0327(11) 0.066(4) Uani 1 1 d . . .
H22A H 0.3368 0.0589 -0.1120 0.079 Uiso 1 1 calc R . .
H22B H 0.3292 -0.0737 -0.0399 0.079 Uiso 1 1 calc R . .
C21 C 0.3927(8) 0.0613(19) 0.0497(14) 0.101(5) Uani 1 1 d . . .
H21A H 0.3866 0.0275 0.1290 0.151 Uiso 1 1 calc R . .
H21B H 0.3967 0.1567 0.0527 0.151 Uiso 1 1 calc R . .
H21C H 0.4342 0.0242 0.0194 0.151 Uiso 1 1 calc R . .
C19 C 0.2543(8) 0.2165(12) 0.0189(10) 0.067(4) Uani 1 1 d . . .
H19A H 0.2906 0.2501 0.0745 0.080 Uiso 1 1 calc R . .
H19B H 0.2101 0.2368 0.0520 0.080 Uiso 1 1 calc R . .
C20 C 0.2585(7) 0.2883(13) -0.0990(11) 0.067(4) Uani 1 1 d . . .
H20A H 0.3059 0.2915 -0.1208 0.100 Uiso 1 1 calc R . .
H20B H 0.2411 0.3774 -0.0915 0.100 Uiso 1 1 calc R . .
H20C H 0.2311 0.2418 -0.1601 0.100 Uiso 1 1 calc R . .


_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
O4 C10 1.369(12) . ?
O4 C11 1.377(11) . ?
O2 N1 1.233(13) . ?
O1 N1 1.232(13) . ?
O3 C8 1.280(11) . ?
O3 H3A 0.8200 . ?
O5 C11 1.238(11) . ?
N2 C4 1.356(13) . ?
N2 C7 1.429(11) . ?
N2 H2 0.8600 . ?
N1 C1 1.456(15) . ?
C7 C8 1.368(13) . ?
C7 C11 1.407(12) . ?
C13 C12 1.386(14) . ?
C13 C14 1.404(14) . ?
C13 C16 1.506(15) . ?
C10 C15 1.375(14) . ?
C10 C9 1.410(13) . ?
C15 C14 1.388(15) . ?
C15 H15 0.9300 . ?
C14 H14 0.9300 . ?
C12 C9 1.398(14) . ?
C12 H12 0.9300 . ?
C9 C8 1.496(13) . ?
C4 C5 1.413(14) . ?
C4 C3 1.430(14) . ?
C3 C2 1.379(16) . ?
C3 H3 0.9300 . ?
C2 C1 1.376(15) . ?
C2 H2A 0.9300 . ?
C1 C6 1.382(16) . ?
C6 C5 1.370(15) . ?
C6 H6 0.9300 . ?
C5 H5 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
N3 C18 1.465(14) . ?
N3 C19 1.473(14) . ?
N3 C22 1.520(14) . ?
C17 C18 1.54(2) . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C22 C21 1.523(18) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C19 C20 1.505(16) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C10 O4 C11 121.9(7) . . ?
C8 O3 H3A 109.5 . . ?
C4 N2 C7 124.8(8) . . ?
C4 N2 H2 117.6 . . ?
C7 N2 H2 117.6 . . ?
O1 N1 O2 124.3(11) . . ?
O1 N1 C1 118.6(10) . . ?
O2 N1 C1 117.1(11) . . ?
C8 C7 C11 123.6(8) . . ?
C8 C7 N2 118.7(8) . . ?
C11 C7 N2 117.6(8) . . ?
C12 C13 C14 119.1(9) . . ?
C12 C13 C16 122.7(9) . . ?
C14 C13 C16 118.2(9) . . ?
O5 C11 O4 115.0(8) . . ?
O5 C11 C7 126.4(9) . . ?
O4 C11 C7 118.5(8) . . ?
O4 C10 C15 118.4(8) . . ?
O4 C10 C9 120.9(8) . . ?
C15 C10 C9 120.7(9) . . ?
C10 C15 C14 119.9(9) . . ?
C10 C15 H15 120.0 . . ?
C14 C15 H15 120.0 . . ?
C15 C14 C13 120.6(9) . . ?
C15 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C13 C12 C9 120.9(9) . . ?
C13 C12 H12 119.5 . . ?
C9 C12 H12 119.5 . . ?
C12 C9 C10 118.7(9) . . ?
C12 C9 C8 123.0(8) . . ?
C10 C9 C8 118.3(8) . . ?
O3 C8 C7 126.7(9) . . ?
O3 C8 C9 116.8(8) . . ?
C7 C8 C9 116.5(8) . . ?
N2 C4 C5 123.8(10) . . ?
N2 C4 C3 119.9(9) . . ?
C5 C4 C3 116.2(9) . . ?
C2 C3 C4 121.2(10) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?
C1 C2 C3 119.6(11) . . ?
C1 C2 H2A 120.2 . . ?
C3 C2 H2A 120.2 . . ?
C2 C1 C6 121.3(10) . . ?
C2 C1 N1 119.2(11) . . ?
C6 C1 N1 119.6(10) . . ?
C5 C6 C1 119.5(10) . . ?
C5 C6 H6 120.2 . . ?
C1 C6 H6 120.2 . . ?
C6 C5 C4 122.0(10) . . ?
C6 C5 H5 119.0 . . ?
C4 C5 H5 119.0 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C13 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C18 N3 C19 112.9(9) . . ?
C18 N3 C22 111.3(9) . . ?
C19 N3 C22 115.0(10) . . ?
C18 C17 H17A 109.5 . . ?
C18 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C18 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N3 C18 C17 112.8(10) . . ?
N3 C18 H18A 109.0 . . ?
C17 C18 H18A 109.0 . . ?
N3 C18 H18B 109.0 . . ?
C17 C18 H18B 109.0 . . ?
H18A C18 H18B 107.8 . . ?
N3 C22 C21 114.0(11) . . ?
N3 C22 H22A 108.8 . . ?
C21 C22 H22A 108.8 . . ?
N3 C22 H22B 108.8 . . ?
C21 C22 H22B 108.8 . . ?
H22A C22 H22B 107.6 . . ?
C22 C21 H21A 109.5 . . ?
C22 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C22 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
N3 C19 C20 114.0(9) . . ?
N3 C19 H19A 108.7 . . ?
C20 C19 H19A 108.7 . . ?
N3 C19 H19B 108.7 . . ?
C20 C19 H19B 108.7 . . ?
H19A C19 H19B 107.6 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 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
C4 N2 C7 C8 124.4(10) . . . . ?
C4 N2 C7 C11 -58.9(13) . . . . ?
C10 O4 C11 O5 -176.5(9) . . . . ?
C10 O4 C11 C7 5.6(13) . . . . ?
C8 C7 C11 O5 177.0(10) . . . . ?
N2 C7 C11 O5 0.5(15) . . . . ?
C8 C7 C11 O4 -5.4(14) . . . . ?
N2 C7 C11 O4 178.1(8) . . . . ?
C11 O4 C10 C15 178.7(9) . . . . ?
C11 O4 C10 C9 -1.6(14) . . . . ?
O4 C10 C15 C14 -178.6(9) . . . . ?
C9 C10 C15 C14 1.7(16) . . . . ?
C10 C15 C14 C13 -0.3(17) . . . . ?
C12 C13 C14 C15 -0.5(17) . . . . ?
C16 C13 C14 C15 179.2(11) . . . . ?
C14 C13 C12 C9 -0.1(16) . . . . ?
C16 C13 C12 C9 -179.7(11) . . . . ?
C13 C12 C9 C10 1.4(15) . . . . ?
C13 C12 C9 C8 -177.7(10) . . . . ?
O4 C10 C9 C12 178.1(9) . . . . ?
C15 C10 C9 C12 -2.2(15) . . . . ?
O4 C10 C9 C8 -2.7(13) . . . . ?
C15 C10 C9 C8 176.9(9) . . . . ?
C11 C7 C8 O3 -177.7(9) . . . . ?
N2 C7 C8 O3 -1.3(15) . . . . ?
C11 C7 C8 C9 1.1(14) . . . . ?
N2 C7 C8 C9 177.5(8) . . . . ?
C12 C9 C8 O3 1.0(14) . . . . ?
C10 C9 C8 O3 -178.1(8) . . . . ?
C12 C9 C8 C7 -177.9(9) . . . . ?
C10 C9 C8 C7 3.0(13) . . . . ?
C7 N2 C4 C5 -7.9(15) . . . . ?
C7 N2 C4 C3 175.9(9) . . . . ?
N2 C4 C3 C2 -179.3(10) . . . . ?
C5 C4 C3 C2 4.1(15) . . . . ?
C4 C3 C2 C1 -2.9(17) . . . . ?
C3 C2 C1 C6 0.2(18) . . . . ?
C3 C2 C1 N1 179.6(11) . . . . ?
O1 N1 C1 C2 -4.4(17) . . . . ?
O2 N1 C1 C2 175.8(12) . . . . ?
O1 N1 C1 C6 175.0(12) . . . . ?
O2 N1 C1 C6 -4.8(17) . . . . ?
C2 C1 C6 C5 1.1(18) . . . . ?
N1 C1 C6 C5 -178.3(11) . . . . ?
C1 C6 C5 C4 0.3(17) . . . . ?
N2 C4 C5 C6 -179.2(10) . . . . ?
C3 C4 C5 C6 -2.8(15) . . . . ?
C19 N3 C18 C17 73.7(13) . . . . ?
C22 N3 C18 C17 -155.3(10) . . . . ?
C18 N3 C22 C21 -68.2(14) . . . . ?
C19 N3 C22 C21 61.7(14) . . . . ?
C18 N3 C19 C20 -168.5(11) . . . . ?
C22 N3 C19 C20 62.4(14) . . . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         1.048
_refine_diff_density_min         -0.522
_refine_diff_density_rms         0.170

# start Validation Reply Form
_vrf_PLAT082_platon              
;
PROBLEM: ALERT_2_A High R1 Value .................................. 0.22 Report
RESPONSE: The crystal structure parameters are of low quality. Every
crystal was found to be weak and consist of very thin and flexible needles.
However, it is useful to extract for the confirmation of the structure 
of the expected molecule. Crystallization attemps with other conditions were
unsuccessful.
;
_vrf_PLAT084_platon              
;
PROBLEM: High wR2 Value (i.e. > 0.25) ................... 0.55 Report
RESPONSE: Due to same explanation as above.
;

# end Validation Reply Form_shelxl_version_number 97
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_exp_5644
_database_code_depnum_ccdc_archive 'CCDC 1866322'
_audit_update_record             
;
2018-09-06 deposited with the CCDC.
2018-11-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        unk
_chemical_name_common            ?
_chemical_formula_moiety         'C22 H17 N O'
_chemical_formula_sum            'C22 H17 N O'
_chemical_compound_source        synthesis
_exptl_crystal_recrystallization_method 'ethyl acetate and hexane'
_chemical_melting_point          ?

_exptl_crystal_description       needle
_exptl_crystal_colour            brown

_diffrn_ambient_temperature      293(2)
_chemical_formula_weight         311.37

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'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_int_tables_number      19
_chemical_absolute_configuration ?

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

_cell_length_a                   10.4148(15)
_cell_length_b                   10.5315(9)
_cell_length_c                   15.0526(18)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1651.0(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4218
_cell_measurement_theta_min      3.33
_cell_measurement_theta_max      24.99
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.24
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.253
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             656
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.975
_exptl_absorpt_correction_T_max  0.982
_exptl_absorpt_process_details   ?

_exptl_special_details           
; 
 ? 
;
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4179
_diffrn_reflns_av_R_equivalents  0.0432
_diffrn_reflns_av_sigmaI/netI    0.1235
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         3.33
_diffrn_reflns_theta_max         24.99
_reflns_number_total             2677
_reflns_number_gt                1282
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0280P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -3(5)
_refine_ls_number_reflns         2677
_refine_ls_number_parameters     218
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1505
_refine_ls_R_factor_gt           0.0669
_refine_ls_wR_factor_ref         0.1412
_refine_ls_wR_factor_gt          0.0983
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O24 O 0.2271(5) 0.2783(3) 0.3210(3) 0.0826(14) Uani 1 1 d . . .
H24 H 0.2279 0.3407 0.3535 0.124 Uiso 1 1 calc R . .
N11 N 0.3502(4) 0.5116(4) 0.2999(3) 0.0546(12) Uani 1 1 d . . .
C2 C 0.3995(5) 0.4492(5) 0.1442(3) 0.0463(14) Uani 1 1 d . . .
C12 C 0.4338(6) 0.4842(5) 0.3716(3) 0.0482(13) Uani 1 1 d . . .
C1 C 0.3429(5) 0.4230(4) 0.2273(3) 0.0494(14) Uani 1 1 d . . .
C13 C 0.5481(5) 0.4211(4) 0.3556(4) 0.0542(15) Uani 1 1 d . . .
H13 H 0.5706 0.3999 0.2976 0.065 Uiso 1 1 calc R . .
C10 C 0.2820(6) 0.3089(5) 0.2407(4) 0.0573(15) Uani 1 1 d . . .
C3 C 0.4646(6) 0.5635(5) 0.1270(4) 0.0595(16) Uani 1 1 d . . .
H3 H 0.4716 0.6248 0.1712 0.071 Uiso 1 1 calc R . .
C8 C 0.3234(6) 0.2434(5) 0.0921(4) 0.0653(18) Uani 1 1 d . . .
H8 H 0.3174 0.1828 0.0473 0.078 Uiso 1 1 calc R . .
C18 C 0.2759(5) 0.6241(5) 0.2946(3) 0.0526(14) Uani 1 1 d . . .
C23 C 0.3155(5) 0.7334(5) 0.3372(4) 0.0590(16) Uani 1 1 d . . .
H23 H 0.3905 0.7334 0.3707 0.071 Uiso 1 1 calc R . .
C14 C 0.6285(6) 0.3893(5) 0.4242(4) 0.0708(19) Uani 1 1 d . . .
H14 H 0.7053 0.3476 0.4124 0.085 Uiso 1 1 calc R . .
C7 C 0.3865(6) 0.3581(5) 0.0753(4) 0.0555(16) Uani 1 1 d . . .
C6 C 0.4442(6) 0.3845(6) -0.0076(4) 0.0704(19) Uani 1 1 d . . .
H6 H 0.4372 0.3249 -0.0529 0.084 Uiso 1 1 calc R . .
C9 C 0.2708(6) 0.2191(5) 0.1727(4) 0.0706(19) Uani 1 1 d . . .
H9 H 0.2274 0.1432 0.1827 0.085 Uiso 1 1 calc R . .
C22 C 0.2432(6) 0.8431(5) 0.3298(4) 0.0698(18) Uani 1 1 d . . .
H22 H 0.2689 0.9164 0.3592 0.084 Uiso 1 1 calc R . .
C19 C 0.1654(5) 0.6253(6) 0.2449(4) 0.0670(17) Uani 1 1 d . . .
H19 H 0.1380 0.5518 0.2163 0.080 Uiso 1 1 calc R . .
C21 C 0.1340(7) 0.8440(6) 0.2793(4) 0.078(2) Uani 1 1 d . . .
H21 H 0.0863 0.9182 0.2736 0.094 Uiso 1 1 calc R . .
C15 C 0.5966(8) 0.4185(6) 0.5101(4) 0.078(2) Uani 1 1 d . . .
H15 H 0.6502 0.3956 0.5569 0.094 Uiso 1 1 calc R . .
C4 C 0.5177(6) 0.5846(6) 0.0451(4) 0.0758(19) Uani 1 1 d . . .
H4 H 0.5603 0.6606 0.0344 0.091 Uiso 1 1 calc R . .
C5 C 0.5093(6) 0.4933(7) -0.0236(4) 0.081(2) Uani 1 1 d . . .
H5 H 0.5476 0.5077 -0.0785 0.097 Uiso 1 1 calc R . .
C17 C 0.4014(6) 0.5120(6) 0.4582(3) 0.0705(18) Uani 1 1 d . . .
H17 H 0.3235 0.5511 0.4711 0.085 Uiso 1 1 calc R . .
C20 C 0.0951(6) 0.7356(6) 0.2374(4) 0.0795(19) Uani 1 1 d . . .
H20 H 0.0205 0.7363 0.2034 0.095 Uiso 1 1 calc R . .
C16 C 0.4859(7) 0.4812(6) 0.5255(4) 0.080(2) Uani 1 1 d . . .
H16 H 0.4657 0.5044 0.5834 0.096 Uiso 1 1 calc R . .


_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
O24 C10 1.374(6) . ?
O24 H24 0.8200 . ?
N11 C12 1.417(6) . ?
N11 C18 1.417(6) . ?
N11 C1 1.439(6) . ?
C2 C3 1.406(7) . ?
C2 C1 1.410(6) . ?
C2 C7 1.419(6) . ?
C12 C17 1.377(6) . ?
C12 C13 1.385(7) . ?
C1 C10 1.373(6) . ?
C13 C14 1.371(7) . ?
C13 H13 0.9300 . ?
C10 C9 1.399(7) . ?
C3 C4 1.369(7) . ?
C3 H3 0.9300 . ?
C8 C9 1.356(7) . ?
C8 C7 1.398(7) . ?
C8 H8 0.9300 . ?
C18 C19 1.373(7) . ?
C18 C23 1.381(6) . ?
C23 C22 1.383(7) . ?
C23 H23 0.9300 . ?
C14 C15 1.370(8) . ?
C14 H14 0.9300 . ?
C7 C6 1.413(7) . ?
C6 C5 1.352(8) . ?
C6 H6 0.9300 . ?
C9 H9 0.9300 . ?
C22 C21 1.367(8) . ?
C22 H22 0.9300 . ?
C19 C20 1.377(7) . ?
C19 H19 0.9300 . ?
C21 C20 1.366(7) . ?
C21 H21 0.9300 . ?
C15 C16 1.349(9) . ?
C15 H15 0.9300 . ?
C4 C5 1.415(7) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C17 C16 1.381(7) . ?
C17 H17 0.9300 . ?
C20 H20 0.9300 . ?
C16 H16 0.9300 . ?

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
C10 O24 H24 109.5 . . ?
C12 N11 C18 123.3(4) . . ?
C12 N11 C1 118.6(4) . . ?
C18 N11 C1 118.1(4) . . ?
C3 C2 C1 122.2(5) . . ?
C3 C2 C7 119.4(5) . . ?
C1 C2 C7 118.4(5) . . ?
C17 C12 C13 118.5(5) . . ?
C17 C12 N11 121.8(5) . . ?
C13 C12 N11 119.6(5) . . ?
C10 C1 C2 119.7(5) . . ?
C10 C1 N11 118.7(5) . . ?
C2 C1 N11 121.6(4) . . ?
C14 C13 C12 120.7(6) . . ?
C14 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
C1 C10 O24 121.8(5) . . ?
C1 C10 C9 121.5(5) . . ?
O24 C10 C9 116.8(5) . . ?
C4 C3 C2 119.9(5) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C9 C8 C7 121.0(5) . . ?
C9 C8 H8 119.5 . . ?
C7 C8 H8 119.5 . . ?
C19 C18 C23 119.7(5) . . ?
C19 C18 N11 119.8(5) . . ?
C23 C18 N11 120.5(5) . . ?
C18 C23 C22 119.7(6) . . ?
C18 C23 H23 120.1 . . ?
C22 C23 H23 120.1 . . ?
C15 C14 C13 120.6(6) . . ?
C15 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C8 C7 C6 122.0(6) . . ?
C8 C7 C2 119.8(6) . . ?
C6 C7 C2 118.1(5) . . ?
C5 C6 C7 122.5(6) . . ?
C5 C6 H6 118.8 . . ?
C7 C6 H6 118.8 . . ?
C8 C9 C10 119.6(5) . . ?
C8 C9 H9 120.2 . . ?
C10 C9 H9 120.2 . . ?
C21 C22 C23 120.3(6) . . ?
C21 C22 H22 119.9 . . ?
C23 C22 H22 119.9 . . ?
C18 C19 C20 119.8(6) . . ?
C18 C19 H19 120.1 . . ?
C20 C19 H19 120.1 . . ?
C20 C21 C22 119.8(6) . . ?
C20 C21 H21 120.1 . . ?
C22 C21 H21 120.1 . . ?
C16 C15 C14 118.6(7) . . ?
C16 C15 H15 120.7 . . ?
C14 C15 H15 120.7 . . ?
C3 C4 C5 121.5(6) . . ?
C3 C4 H4 119.2 . . ?
C5 C4 H4 119.2 . . ?
C6 C5 C4 118.5(6) . . ?
C6 C5 H5 120.8 . . ?
C4 C5 H5 120.8 . . ?
C12 C17 C16 119.2(6) . . ?
C12 C17 H17 120.4 . . ?
C16 C17 H17 120.4 . . ?
C21 C20 C19 120.7(6) . . ?
C21 C20 H20 119.7 . . ?
C19 C20 H20 119.7 . . ?
C15 C16 C17 122.3(6) . . ?
C15 C16 H16 118.9 . . ?
C17 C16 H16 118.9 . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.996
_refine_diff_density_max         0.166
_refine_diff_density_min         -0.165
_refine_diff_density_rms         0.041

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 1866321'
_audit_update_record             
;
2018-09-06 deposited with the CCDC.
2018-11-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        unk
_chemical_name_common            ?
_chemical_formula_moiety         'C18 H15 N O3'
_chemical_formula_sum            'C2.48 H2.07 N0.14 O0.41'
_chemical_compound_source        synthesis
_exptl_crystal_recrystallization_method 'ethyl acetate and hexane'
_chemical_melting_point          ?

_exptl_crystal_description       needle
_exptl_crystal_colour            brown

_diffrn_ambient_temperature      296(2)
_chemical_formula_weight         40.46

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 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      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_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, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   13.692(3)
_cell_length_b                   9.810(2)
_cell_length_c                   21.438(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2879.4(11)
_cell_formula_units_Z            58
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    19610
_cell_measurement_theta_min      1.90
_cell_measurement_theta_max      25.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_F_000             1232
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.21
_exptl_absorpt_coefficient_mu    0.093
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.972
_exptl_absorpt_correction_T_max  0.981
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            17752
_diffrn_reflns_av_unetI/netI     0.0324
_diffrn_reflns_av_R_equivalents  0.0476
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.900
_diffrn_reflns_theta_max         25.050
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_point_group_measured_fraction_full 0.974
_reflns_number_total             2536
_reflns_number_gt                1819
_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       'CrysAlisPro, Agilent Technologies'
_computing_cell_refinement       'CrysAlisPro, Agilent Technologies'
_computing_data_reduction        'CrysAlisPro, Agilent Technologies'
_computing_structure_solution    'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Brucker SHELXTL'
_computing_publication_material  'Brucker SHELXTL'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0721P)²+0.1281P] 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         2536
_refine_ls_number_parameters     205
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0661
_refine_ls_R_factor_gt           0.0463
_refine_ls_wR_factor_ref         0.1312
_refine_ls_wR_factor_gt          0.1193
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.053
_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
C6 C 0.79917(13) 0.27077(18) 0.69518(9) 0.0495(5) Uani 1 1 d . . . . .
C1 C 0.78555(13) 0.21935(17) 0.63441(9) 0.0476(5) Uani 1 1 d . . . . .
C2 C 0.85152(13) 0.13009(17) 0.60963(9) 0.0515(5) Uani 1 1 d . . . . .
C5 C 0.88470(14) 0.23366(19) 0.72896(10) 0.0550(5) Uani 1 1 d . . . . .
C7 C 0.73225(15) 0.3592(2) 0.72412(10) 0.0604(6) Uani 1 1 d . . . . .
H7 H 0.6749 0.3824 0.7035 0.072 Uiso 1 1 calc R U . . .
C3 C 0.93540(14) 0.09220(19) 0.64362(10) 0.0597(6) Uani 1 1 d . . . . .
H3 H 0.9801 0.0316 0.6263 0.072 Uiso 1 1 calc R U . . .
C10 C 0.89986(17) 0.2890(2) 0.78810(11) 0.0703(6) Uani 1 1 d . . . . .
H10 H 0.9557 0.2656 0.8103 0.084 Uiso 1 1 calc R U . . .
C4 C 0.95098(15) 0.14321(19) 0.70069(10) 0.0602(6) Uani 1 1 d . . . . .
H4 H 1.0072 0.1181 0.7222 0.072 Uiso 1 1 calc R U . . .
C8 C 0.75019(19) 0.4112(3) 0.78184(11) 0.0773(7) Uani 1 1 d . . . . .
H8 H 0.7056 0.4707 0.8000 0.093 Uiso 1 1 calc R U . . .
C9 C 0.8347(2) 0.3760(3) 0.81359(12) 0.0792(7) Uani 1 1 d . . . . .
H9 H 0.8466 0.4126 0.8529 0.095 Uiso 1 1 calc R U . . .
C13 C 0.46018(13) 0.15009(18) 0.54993(8) 0.0460(5) Uani 1 1 d . . . . .
H13 H 0.4096 0.1800 0.5244 0.055 Uiso 1 1 calc R U . . .
C12 C 0.54030(12) 0.23116(17) 0.55848(8) 0.0450(5) Uani 1 1 d . . . . .
H12 H 0.5430 0.3165 0.5396 0.054 Uiso 1 1 calc R U . . .
C14 C 0.45330(12) 0.02428(17) 0.57870(8) 0.0447(4) Uani 1 1 d . . . . .
C15 C 0.52761(13) -0.01557(18) 0.61826(8) 0.0518(5) Uani 1 1 d . . . . .
H15 H 0.5227 -0.0980 0.6394 0.062 Uiso 1 1 calc R U . . .
C11 C 0.61758(12) 0.18684(17) 0.59516(8) 0.0445(5) Uani 1 1 d . . . . .
C16 C 0.60846(13) 0.06455(18) 0.62680(9) 0.0513(5) Uani 1 1 d . . . . .
H16 H 0.6575 0.0366 0.6540 0.062 Uiso 1 1 calc R U . . .
O1 O 0.84253(10) 0.07077(14) 0.55278(7) 0.0673(4) Uani 1 1 d . . . . .
H1 H 0.7922 0.0975 0.5360 0.101 Uiso 1 1 calc R U . . .
O2 O 0.38172(10) -0.18856(15) 0.59117(7) 0.0652(4) Uani 1 1 d . . . . .
O3 O 0.30383(10) -0.03850(14) 0.53096(7) 0.0645(4) Uani 1 1 d . . . . .
C18 C 0.37145(13) -0.06774(19) 0.56436(9) 0.0496(5) Uani 1 1 d . . . . .
C17 C 0.30977(17) -0.2914(2) 0.57743(12) 0.0780(7) Uani 1 1 d . . . . .
H17A H 0.2510 -0.2486 0.5629 0.117 Uiso 1 1 calc R U . . .
H17B H 0.2960 -0.3429 0.6145 0.117 Uiso 1 1 calc R U . . .
H17C H 0.3344 -0.3513 0.5457 0.117 Uiso 1 1 calc R U . . .
N1 N 0.70344(11) 0.26051(17) 0.59801(8) 0.0529(5) Uani 1 1 d . . . . .
H1A H 0.7009(15) 0.346(2) 0.5863(10) 0.074(7) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C6 C7 1.406(3) . ?
C6 C1 1.410(3) . ?
C6 C5 1.424(3) . ?
C1 C2 1.366(2) . ?
C1 N1 1.427(2) . ?
C2 O1 1.356(2) . ?
C2 C3 1.410(3) . ?
C5 C10 1.395(3) . ?
C5 C4 1.406(3) . ?
C7 C8 1.361(3) . ?
C3 C4 1.339(3) . ?
C10 C9 1.351(3) . ?
C8 C9 1.386(3) . ?
C13 C12 1.367(2) . ?
C13 C14 1.383(2) . ?
C12 C11 1.388(2) . ?
C14 C15 1.381(2) . ?
C14 C18 1.472(2) . ?
C15 C16 1.370(2) . ?
C11 N1 1.381(2) . ?
C11 C16 1.384(2) . ?
O2 C18 1.325(2) . ?
O2 C17 1.441(2) . ?
O3 C18 1.205(2) . ?

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
C7 C6 C1 122.86(18) . . ?
C7 C6 C5 117.98(19) . . ?
C1 C6 C5 119.16(18) . . ?
C2 C1 C6 120.11(17) . . ?
C2 C1 N1 119.33(18) . . ?
C6 C1 N1 120.56(17) . . ?
O1 C2 C1 124.38(17) . . ?
O1 C2 C3 115.17(17) . . ?
C1 C2 C3 120.44(19) . . ?
C10 C5 C4 122.8(2) . . ?
C10 C5 C6 119.0(2) . . ?
C4 C5 C6 118.22(19) . . ?
C8 C7 C6 121.0(2) . . ?
C4 C3 C2 120.24(19) . . ?
C9 C10 C5 121.0(2) . . ?
C3 C4 C5 121.78(19) . . ?
C7 C8 C9 120.2(2) . . ?
C10 C9 C8 120.7(2) . . ?
C12 C13 C14 120.92(16) . . ?
C13 C12 C11 120.36(16) . . ?
C15 C14 C13 118.45(16) . . ?
C15 C14 C18 121.04(17) . . ?
C13 C14 C18 120.41(16) . . ?
C16 C15 C14 120.99(17) . . ?
N1 C11 C16 120.58(16) . . ?
N1 C11 C12 120.66(16) . . ?
C16 C11 C12 118.71(16) . . ?
C15 C16 C11 120.32(16) . . ?
C18 O2 C17 117.73(16) . . ?
O3 C18 O2 123.53(17) . . ?
O3 C18 C14 124.28(18) . . ?
O2 C18 C14 112.17(16) . . ?
C11 N1 C1 123.14(15) . . ?

_refine_diff_density_max         0.209
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.036

_shelxl_version_number           2013-4

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_h-m   ?
_symmetry_int_tables_number      ?
_chemical_absolute_configuration ?

####################################################################### 
# 
# 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_sr2-830
_database_code_depnum_ccdc_archive 'CCDC 1866323'
_audit_update_record             
;
2018-09-06 deposited with the CCDC.
2018-11-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        unk
_chemical_name_common            ?
_chemical_formula_moiety         'C19 H16 Br N O3'
_chemical_formula_sum            'C19 H16 Br N O3'
_chemical_compound_source        synthesis
_exptl_crystal_recrystallization_method 'ethyl acetate and hexane'
_chemical_melting_point          ?

_exptl_crystal_description       block
_exptl_crystal_colour            brown

_diffrn_ambient_temperature      293(2)
_chemical_formula_weight         386.24

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'
Br Br -0.2901 2.4595 '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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_int_tables_number      14
_chemical_absolute_configuration ?

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

_cell_length_a                   11.6484(7)
_cell_length_b                   13.0417(5)
_cell_length_c                   11.0000(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 91.035(5)
_cell_angle_gamma                90.00
_cell_volume                     1670.79(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    6747
_cell_measurement_theta_min      2.97
_cell_measurement_theta_max      25.00
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.36
_exptl_crystal_size_min          0.31
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.535
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             784
_exptl_absorpt_coefficient_mu    2.477
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.377
_exptl_absorpt_correction_T_max  0.464
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6195
_diffrn_reflns_av_R_equivalents  0.0423
_diffrn_reflns_av_sigmaI/netI    0.0679
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.97
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2903
_reflns_number_gt                2030
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro, Agilent Technologies'
_computing_cell_refinement       'CrysAlisPro, Agilent Technologies'
_computing_data_reduction        'CrysAlisPro, Agilent Technologies'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0632P)²+0.1331P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2903
_refine_ls_number_parameters     223
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0819
_refine_ls_R_factor_gt           0.0501
_refine_ls_wR_factor_ref         0.1489
_refine_ls_wR_factor_gt          0.1238
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.75048(5) -0.04322(4) 0.52117(6) 0.0834(3) Uani 1 1 d . . .
O2 O 0.8272(2) 0.66027(19) 0.4089(2) 0.0457(7) Uani 1 1 d . . .
O1 O 0.8806(2) 0.1426(2) 0.5858(3) 0.0532(8) Uani 1 1 d . . .
H1 H 0.9077 0.2006 0.5882 0.080 Uiso 1 1 calc R . .
O3 O 0.9845(2) 0.70708(19) 0.5147(2) 0.0500(7) Uani 1 1 d . . .
N1 N 0.8452(3) 0.2884(3) 0.7744(3) 0.0461(9) Uani 1 1 d . . .
C12 C 0.9368(3) 0.4505(3) 0.7430(3) 0.0365(9) Uani 1 1 d . . .
H12 H 0.9826 0.4397 0.8119 0.044 Uiso 1 1 calc R . .
C13 C 0.9524(3) 0.5371(3) 0.6741(4) 0.0368(9) Uani 1 1 d . . .
H13 H 1.0094 0.5838 0.6961 0.044 Uiso 1 1 calc R . .
C17 C 0.9052(3) 0.6475(3) 0.4976(3) 0.0388(9) Uani 1 1 d . . .
C14 C 0.8836(3) 0.5558(3) 0.5715(4) 0.0352(9) Uani 1 1 d . . .
C11 C 0.8529(3) 0.3787(3) 0.7105(3) 0.0338(8) Uani 1 1 d . . .
C15 C 0.7982(3) 0.4854(3) 0.5421(4) 0.0381(9) Uani 1 1 d . . .
H15 H 0.7504 0.4975 0.4750 0.046 Uiso 1 1 calc R . .
C16 C 0.7826(3) 0.3985(3) 0.6100(3) 0.0409(9) Uani 1 1 d . . .
H16 H 0.7246 0.3526 0.5885 0.049 Uiso 1 1 calc R . .
C1 C 0.7646(3) 0.2081(3) 0.7492(3) 0.0370(9) Uani 1 1 d . . .
C2 C 0.7889(3) 0.1376(3) 0.6597(3) 0.0397(9) Uani 1 1 d . . .
C9 C 0.6641(3) 0.1989(3) 0.8197(3) 0.0397(9) Uani 1 1 d . . .
C3 C 0.7145(4) 0.0523(3) 0.6439(4) 0.0455(10) Uani 1 1 d . . .
C10 C 0.5929(3) 0.1108(3) 0.8039(4) 0.0439(10) Uani 1 1 d . . .
C4 C 0.6215(4) 0.0383(3) 0.7138(4) 0.0477(11) Uani 1 1 d . . .
H4 H 0.5759 -0.0196 0.7025 0.057 Uiso 1 1 calc R . .
C18 C 0.8412(3) 0.7469(3) 0.3283(4) 0.0500(11) Uani 1 1 d . . .
H18A H 0.8981 0.7315 0.2676 0.060 Uiso 1 1 calc R . .
H18B H 0.8664 0.8067 0.3739 0.060 Uiso 1 1 calc R . .
C8 C 0.6311(4) 0.2739(3) 0.9050(4) 0.0490(11) Uani 1 1 d . . .
H8 H 0.6744 0.3334 0.9145 0.059 Uiso 1 1 calc R . .
C5 C 0.4966(4) 0.0986(4) 0.8788(4) 0.0552(12) Uani 1 1 d . . .
H5 H 0.4514 0.0402 0.8706 0.066 Uiso 1 1 calc R . .
C6 C 0.4684(4) 0.1714(4) 0.9636(4) 0.0553(12) Uani 1 1 d . . .
H6 H 0.4055 0.1623 1.0133 0.066 Uiso 1 1 calc R . .
C7 C 0.5362(4) 0.2594(4) 0.9733(4) 0.0615(13) Uani 1 1 d . . .
H7 H 0.5158 0.3099 1.0284 0.074 Uiso 1 1 calc R . .
C19 C 0.7282(4) 0.7668(4) 0.2689(4) 0.0671(14) Uani 1 1 d . . .
H19A H 0.7060 0.7085 0.2207 0.101 Uiso 1 1 calc R . .
H19B H 0.7335 0.8261 0.2177 0.101 Uiso 1 1 calc R . .
H19C H 0.6718 0.7786 0.3300 0.101 Uiso 1 1 calc R . .
H100 H 0.882(4) 0.280(3) 0.845(4) 0.053(12) Uiso 1 1 d . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Br1 C3 1.889(4) . ?
O2 C17 1.332(4) . ?
O2 C18 1.448(5) . ?
O1 C2 1.355(4) . ?
O1 H1 0.8200 . ?
O3 C17 1.219(4) . ?
N1 C11 1.376(5) . ?
N1 C1 1.429(5) . ?
N1 H100 0.89(4) . ?
C12 C13 1.374(5) . ?
C12 C11 1.396(5) . ?
C12 H12 0.9300 . ?
C13 C14 1.393(5) . ?
C13 H13 0.9300 . ?
C17 C14 1.470(5) . ?
C14 C15 1.387(5) . ?
C11 C16 1.388(5) . ?
C15 C16 1.371(5) . ?
C15 H15 0.9300 . ?
C16 H16 0.9300 . ?
C1 C2 1.380(5) . ?
C1 C9 1.421(5) . ?
C2 C3 1.419(5) . ?
C9 C8 1.413(5) . ?
C9 C10 1.426(5) . ?
C3 C4 1.353(6) . ?
C10 C5 1.413(6) . ?
C10 C4 1.414(6) . ?
C4 H4 0.9300 . ?
C18 C19 1.482(5) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C8 C7 1.361(6) . ?
C8 H8 0.9300 . ?
C5 C6 1.375(6) . ?
C5 H5 0.9300 . ?
C6 C7 1.395(6) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C17 O2 C18 117.6(3) . . ?
C2 O1 H1 109.5 . . ?
C11 N1 C1 125.2(3) . . ?
C11 N1 H100 121(3) . . ?
C1 N1 H100 112(3) . . ?
C13 C12 C11 120.6(3) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C12 C13 C14 120.7(3) . . ?
C12 C13 H13 119.6 . . ?
C14 C13 H13 119.6 . . ?
O3 C17 O2 122.6(3) . . ?
O3 C17 C14 124.8(3) . . ?
O2 C17 C14 112.6(3) . . ?
C15 C14 C13 118.2(3) . . ?
C15 C14 C17 122.6(3) . . ?
C13 C14 C17 119.2(3) . . ?
N1 C11 C16 121.6(3) . . ?
N1 C11 C12 119.7(3) . . ?
C16 C11 C12 118.7(3) . . ?
C16 C15 C14 121.4(3) . . ?
C16 C15 H15 119.3 . . ?
C14 C15 H15 119.3 . . ?
C15 C16 C11 120.4(3) . . ?
C15 C16 H16 119.8 . . ?
C11 C16 H16 119.8 . . ?
C2 C1 C9 120.9(3) . . ?
C2 C1 N1 118.9(4) . . ?
C9 C1 N1 120.1(3) . . ?
O1 C2 C1 124.7(3) . . ?
O1 C2 C3 116.7(4) . . ?
C1 C2 C3 118.5(4) . . ?
C8 C9 C1 122.6(4) . . ?
C8 C9 C10 118.4(4) . . ?
C1 C9 C10 119.0(4) . . ?
C4 C3 C2 122.0(4) . . ?
C4 C3 Br1 120.4(3) . . ?
C2 C3 Br1 117.5(3) . . ?
C5 C10 C4 122.2(4) . . ?
C5 C10 C9 119.0(4) . . ?
C4 C10 C9 118.8(4) . . ?
C3 C4 C10 120.6(4) . . ?
C3 C4 H4 119.7 . . ?
C10 C4 H4 119.7 . . ?
O2 C18 C19 107.3(3) . . ?
O2 C18 H18A 110.3 . . ?
C19 C18 H18A 110.3 . . ?
O2 C18 H18B 110.3 . . ?
C19 C18 H18B 110.3 . . ?
H18A C18 H18B 108.5 . . ?
C7 C8 C9 120.2(4) . . ?
C7 C8 H8 119.9 . . ?
C9 C8 H8 119.9 . . ?
C6 C5 C10 121.3(4) . . ?
C6 C5 H5 119.3 . . ?
C10 C5 H5 119.3 . . ?
C5 C6 C7 118.5(4) . . ?
C5 C6 H6 120.7 . . ?
C7 C6 H6 120.7 . . ?
C8 C7 C6 122.5(4) . . ?
C8 C7 H7 118.8 . . ?
C6 C7 H7 118.8 . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?

_diffrn_measured_fraction_theta_max 0.985
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.985
_refine_diff_density_max         0.302
_refine_diff_density_min         -0.622
_refine_diff_density_rms         0.074

####################################################################### 
# 
# 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_shelx_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1866324'
_audit_update_record             
;
2018-09-06 deposited with the CCDC.
2018-11-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        unk
_chemical_name_common            ?
_chemical_formula_moiety         'C19 H17 N O3'
_chemical_formula_sum            'C2.45 H2.19 N0.13 O0.39'
_chemical_compound_source        synthesis
_exptl_crystal_recrystallization_method 'ethyl acetate and hexane'
_chemical_melting_point          ?

_exptl_crystal_description       block
_exptl_crystal_colour            brown

_diffrn_ambient_temperature      296(2)
_chemical_formula_weight         39.66

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.7960(11)
_cell_length_b                   11.9194(12)
_cell_length_c                   11.1919(10)
_cell_angle_alpha                90
_cell_angle_beta                 90.881(6)
_cell_angle_gamma                90
_cell_volume                     1573.4(3)
_cell_formula_units_Z            31
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    18221
_cell_measurement_theta_min      1.727
_cell_measurement_theta_max      25.046
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.297
_exptl_crystal_F_000             648
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.33
_exptl_crystal_size_min          0.31
_exptl_absorpt_coefficient_mu    0.088
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.967
_exptl_absorpt_correction_T_max  0.973
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16900
_diffrn_reflns_av_unetI/netI     0.0251
_diffrn_reflns_av_R_equivalents  0.0361
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         1.727
_diffrn_reflns_theta_max         25.046
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 0.976
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 0.976
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 0.976
_reflns_number_total             2786
_reflns_number_gt                1943
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Brucker SHELXTL'
_computing_publication_material  'Brucker SHELXTL'

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0658P)²+0.4083P] 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         2786
_refine_ls_number_parameters     214
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0721
_refine_ls_R_factor_gt           0.0500
_refine_ls_wR_factor_ref         0.1432
_refine_ls_wR_factor_gt          0.1290
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.050
_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
C8 C 0.66780(17) 0.80974(17) 0.30899(18) 0.0535(5) Uani 1 1 d . . . . .
C9 C 0.58794(18) 0.89979(19) 0.3031(2) 0.0591(6) Uani 1 1 d . . . . .
C7 C 0.64602(19) 0.7207(2) 0.3876(2) 0.0622(6) Uani 1 1 d . . . . .
H7 H 0.6963 0.6608 0.3920 0.075 Uiso 1 1 calc R U . . .
C1 C 0.77866(18) 0.90023(18) 0.15710(19) 0.0561(5) Uani 1 1 d . . . . .
C2 C 0.6996(2) 0.9886(2) 0.1520(2) 0.0718(7) Uani 1 1 d . . . . .
H2 H 0.7097 1.0473 0.0985 0.086 Uiso 1 1 calc R U . . .
C4 C 0.4945(2) 0.8973(2) 0.3773(2) 0.0758(7) Uani 1 1 d . . . . .
H4 H 0.4434 0.9566 0.3750 0.091 Uiso 1 1 calc R U . . .
C3 C 0.6090(2) 0.9885(2) 0.2245(2) 0.0700(7) Uani 1 1 d . . . . .
H3 H 0.5593 1.0490 0.2221 0.084 Uiso 1 1 calc R U . . .
C6 C 0.5522(2) 0.7207(3) 0.4576(2) 0.0805(8) Uani 1 1 d . . . . .
H6 H 0.5389 0.6608 0.5087 0.097 Uiso 1 1 calc R U . . .
C5 C 0.4761(2) 0.8108(3) 0.4526(3) 0.0873(8) Uani 1 1 d . . . . .
H5 H 0.4129 0.8111 0.5011 0.105 Uiso 1 1 calc R U . . .
C10 C 0.76508(17) 0.81425(17) 0.23670(18) 0.0516(5) Uani 1 1 d . . . . .
C13 C 0.96540(16) 0.46395(16) 0.16160(17) 0.0463(5) Uani 1 1 d . . . . .
H13 H 1.0272 0.4184 0.1803 0.056 Uiso 1 1 calc R U . . .
C14 C 0.89003(15) 0.43066(16) 0.07263(16) 0.0435(5) Uani 1 1 d . . . . .
C15 C 0.79999(16) 0.50154(16) 0.04417(17) 0.0485(5) Uani 1 1 d . . . . .
H15 H 0.7487 0.4810 -0.0159 0.058 Uiso 1 1 calc R U . . .
C16 C 0.78557(16) 0.60162(17) 0.10345(17) 0.0488(5) Uani 1 1 d . . . . .
H16 H 0.7252 0.6483 0.0831 0.059 Uiso 1 1 calc R U . . .
C11 C 0.86160(15) 0.63274(16) 0.19384(17) 0.0449(5) Uani 1 1 d . . . . .
C12 C 0.95138(15) 0.56183(16) 0.22251(17) 0.0473(5) Uani 1 1 d . . . . .
H12 H 1.0021 0.5812 0.2835 0.057 Uiso 1 1 calc R U . . .
C17 C 0.90787(17) 0.32317(18) 0.01226(18) 0.0503(5) Uani 1 1 d . . . . .
C18 C 0.8351(2) 0.1915(3) -0.1273(3) 0.0916(9) Uani 1 1 d . . . . .
H18A H 0.8900 0.2006 -0.1903 0.110 Uiso 1 1 calc R U . . .
H18B H 0.8619 0.1328 -0.0739 0.110 Uiso 1 1 calc R U . . .
C19 C 0.7271(2) 0.1609(3) -0.1780(3) 0.1127(12) Uani 1 1 d . . . . .
H19A H 0.6719 0.1577 -0.1160 0.169 Uiso 1 1 calc R U . . .
H19B H 0.7328 0.0888 -0.2156 0.169 Uiso 1 1 calc R U . . .
H19C H 0.7044 0.2159 -0.2364 0.169 Uiso 1 1 calc R U . . .
O2 O 0.98921(12) 0.26235(12) 0.02864(13) 0.0622(4) Uani 1 1 d . . . . .
O1 O 0.82357(12) 0.29631(14) -0.06159(15) 0.0724(5) Uani 1 1 d . . . . .
O3 O 0.86663(14) 0.90817(14) 0.08072(15) 0.0735(5) Uani 1 1 d . . . . .
H3A H 0.9045 0.8506 0.0842 0.110 Uiso 1 1 calc R U . . .
N1 N 0.85369(14) 0.73402(14) 0.25212(17) 0.0561(5) Uani 1 1 d . . . . .
H1 H 0.896(2) 0.743(2) 0.320(2) 0.084(8) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C8 C7 1.404(3) . ?
C8 C10 1.415(3) . ?
C8 C9 1.429(3) . ?
C9 C4 1.390(3) . ?
C9 C3 1.400(3) . ?
C7 C6 1.366(3) . ?
C1 O3 1.358(2) . ?
C1 C10 1.369(3) . ?
C1 C2 1.407(3) . ?
C2 C3 1.352(3) . ?
C4 C5 1.351(4) . ?
C6 C5 1.400(4) . ?
C10 N1 1.425(3) . ?
C13 C12 1.363(3) . ?
C13 C14 1.383(3) . ?
C14 C15 1.390(3) . ?
C14 C17 1.465(3) . ?
C15 C16 1.377(3) . ?
C16 C11 1.392(3) . ?
C11 N1 1.376(2) . ?
C11 C12 1.389(3) . ?
C17 O2 1.214(2) . ?
C17 O1 1.323(2) . ?
C18 C19 1.434(3) . ?
C18 O1 1.457(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 C8 C10 123.0(2) . . ?
C7 C8 C9 118.0(2) . . ?
C10 C8 C9 119.0(2) . . ?
C4 C9 C3 122.8(2) . . ?
C4 C9 C8 119.0(2) . . ?
C3 C9 C8 118.2(2) . . ?
C6 C7 C8 121.1(2) . . ?
O3 C1 C10 124.06(19) . . ?
O3 C1 C2 115.8(2) . . ?
C10 C1 C2 120.2(2) . . ?
C3 C2 C1 120.3(2) . . ?
C5 C4 C9 121.7(2) . . ?
C2 C3 C9 121.9(2) . . ?
C7 C6 C5 120.1(3) . . ?
C4 C5 C6 120.1(3) . . ?
C1 C10 C8 120.30(19) . . ?
C1 C10 N1 119.22(19) . . ?
C8 C10 N1 120.33(19) . . ?
C12 C13 C14 121.62(18) . . ?
C13 C14 C15 118.10(18) . . ?
C13 C14 C17 119.19(17) . . ?
C15 C14 C17 122.71(18) . . ?
C16 C15 C14 121.04(18) . . ?
C15 C16 C11 119.88(18) . . ?
N1 C11 C12 118.79(17) . . ?
N1 C11 C16 122.05(17) . . ?
C12 C11 C16 119.10(18) . . ?
C13 C12 C11 120.23(18) . . ?
O2 C17 O1 122.32(19) . . ?
O2 C17 C14 124.83(19) . . ?
O1 C17 C14 112.83(18) . . ?
C19 C18 O1 109.2(2) . . ?
C17 O1 C18 116.60(18) . . ?
C11 N1 C10 125.89(17) . . ?

_refine_diff_density_max         0.287
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.037

_shelxl_version_number           2013-4

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_h-m   ?
_symmetry_int_tables_number      ?
_chemical_absolute_configuration ?

####################################################################### 
# 
# 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_shelx_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 1866312'
_audit_update_record             
;
2018-09-06 deposited with the CCDC.
2018-11-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        unk
_chemical_name_common            ?
_chemical_formula_moiety         'C16 H12 N2 O3'
_chemical_formula_sum            'C16 H12 N2 O3'
_exptl_crystal_recrystallization_method 'ethyl acetate'
_chemical_melting_point          ?

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow

_diffrn_ambient_temperature      293(2)
_chemical_formula_weight         280.28

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   5.4752(8)
_cell_length_b                   17.649(2)
_cell_length_c                   13.8907(17)
_cell_angle_alpha                90
_cell_angle_beta                 94.311(15)
_cell_angle_gamma                90
_cell_volume                     1338.5(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    4794
_cell_measurement_theta_min      2.941
_cell_measurement_theta_max      24.998
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.391
_exptl_crystal_F_000             584
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.28
_exptl_crystal_size_min          0.23
_exptl_absorpt_coefficient_mu    0.098
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.968
_exptl_absorpt_correction_T_max  0.978
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4555
_diffrn_reflns_av_unetI/netI     0.0955
_diffrn_reflns_av_R_equivalents  0.0412
_diffrn_reflns_limit_h_min       -3
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.941
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measured_fraction_theta_full 0.955
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_Laue_measured_fraction_full 0.955
_diffrn_reflns_point_group_measured_fraction_max 0.978
_diffrn_reflns_point_group_measured_fraction_full 0.955
_reflns_number_total             2317
_reflns_number_gt                1208
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1015P)²+0.5110P] 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     SHELXL
_refine_ls_extinction_coef       0.009(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2317
_refine_ls_number_parameters     196
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1361
_refine_ls_R_factor_gt           0.0775
_refine_ls_wR_factor_ref         0.2356
_refine_ls_wR_factor_gt          0.1733
_refine_ls_goodness_of_fit_ref   0.963
_refine_ls_restrained_S_all      0.963
_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 0.0599(6) 0.81797(15) 0.6154(2) 0.0635(9) Uani 1 1 d . . . . .
H1 H 0.0627 0.8544 0.6521 0.095 Uiso 1 1 calc R U . . .
N1 N 0.0739(6) 0.71325(18) 0.4706(2) 0.0463(9) Uani 1 1 d . . . . .
C11 C 0.0634(7) 0.65483(19) 0.5335(3) 0.0394(9) Uani 1 1 d . . . . .
C9 C 0.4239(7) 0.7815(2) 0.4114(3) 0.0418(10) Uani 1 1 d . . . . .
C1 C 0.2463(7) 0.77408(19) 0.4794(3) 0.0423(10) Uani 1 1 d . . . . .
C10 C 0.5859(7) 0.8441(2) 0.4172(3) 0.0447(10) Uani 1 1 d . . . . .
C2 C 0.2333(8) 0.8272(2) 0.5510(3) 0.0458(10) Uani 1 1 d . . . . .
N2 N 0.0174(11) 0.4757(2) 0.7316(4) 0.0813(14) Uani 1 1 d . . . . .
O3 O -0.1587(10) 0.4342(2) 0.7232(3) 0.1201(17) Uani 1 1 d . . . . .
C16 C 0.2511(7) 0.6422(2) 0.6066(3) 0.0480(10) Uani 1 1 d . . . . .
H16 H 0.3869 0.6740 0.6121 0.058 Uiso 1 1 calc R U . . .
C12 C -0.1350(7) 0.6055(2) 0.5257(3) 0.0500(11) Uani 1 1 d . . . . .
H12 H -0.2585 0.6127 0.4768 0.060 Uiso 1 1 calc R U . . .
C4 C 0.5665(8) 0.8974(2) 0.4928(3) 0.0552(12) Uani 1 1 d . . . . .
H4 H 0.6719 0.9388 0.4976 0.066 Uiso 1 1 calc R U . . .
C8 C 0.4504(8) 0.7277(2) 0.3366(3) 0.0509(11) Uani 1 1 d . . . . .
H8 H 0.3463 0.6860 0.3314 0.061 Uiso 1 1 calc R U . . .
C14 C 0.0367(9) 0.5361(2) 0.6623(3) 0.0556(11) Uani 1 1 d . . . . .
C3 C 0.3964(8) 0.8889(2) 0.5580(3) 0.0561(12) Uani 1 1 d . . . . .
H3 H 0.3875 0.9239 0.6076 0.067 Uiso 1 1 calc R U . . .
C13 C -0.1514(8) 0.5463(2) 0.5891(3) 0.0582(12) Uani 1 1 d . . . . .
H13 H -0.2847 0.5135 0.5836 0.070 Uiso 1 1 calc R U . . .
C5 C 0.7631(8) 0.8511(2) 0.3499(3) 0.0572(12) Uani 1 1 d . . . . .
H5 H 0.8697 0.8922 0.3538 0.069 Uiso 1 1 calc R U . . .
C7 C 0.6243(8) 0.7359(3) 0.2727(3) 0.0580(12) Uani 1 1 d . . . . .
H7 H 0.6385 0.6997 0.2248 0.070 Uiso 1 1 calc R U . . .
C15 C 0.2341(8) 0.5832(2) 0.6698(3) 0.0573(12) Uani 1 1 d . . . . .
H15 H 0.3582 0.5753 0.7182 0.069 Uiso 1 1 calc R U . . .
C6 C 0.7818(8) 0.7981(3) 0.2781(3) 0.0617(13) Uani 1 1 d . . . . .
H6 H 0.8989 0.8037 0.2335 0.074 Uiso 1 1 calc R U . . .
O2 O 0.1760(10) 0.4685(3) 0.7975(4) 0.137(2) Uani 1 1 d . . . . .
H100 H -0.048(10) 0.716(3) 0.423(4) 0.106(19) Uiso 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.362(5) . ?
O1 H1 0.8200 . ?
N1 C11 1.356(5) . ?
N1 C1 1.429(5) . ?
N1 H100 0.91(6) . ?
C11 C12 1.390(5) . ?
C11 C16 1.407(5) . ?
C9 C1 1.412(5) . ?
C9 C10 1.416(5) . ?
C9 C8 1.423(5) . ?
C1 C2 1.373(5) . ?
C10 C5 1.402(6) . ?
C10 C4 1.420(6) . ?
C2 C3 1.407(5) . ?
N2 O3 1.209(6) . ?
N2 O2 1.220(6) . ?
N2 C14 1.445(6) . ?
C16 C15 1.369(5) . ?
C16 H16 0.9300 . ?
C12 C13 1.375(5) . ?
C12 H12 0.9300 . ?
C4 C3 1.355(6) . ?
C4 H4 0.9300 . ?
C8 C7 1.357(6) . ?
C8 H8 0.9300 . ?
C14 C15 1.362(6) . ?
C14 C13 1.404(6) . ?
C3 H3 0.9300 . ?
C13 H13 0.9300 . ?
C5 C6 1.376(6) . ?
C5 H5 0.9300 . ?
C7 C6 1.394(6) . ?
C7 H7 0.9300 . ?
C15 H15 0.9300 . ?
C6 H6 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 O1 H1 109.5 . . ?
C11 N1 C1 125.2(3) . . ?
C11 N1 H100 116(3) . . ?
C1 N1 H100 118(3) . . ?
N1 C11 C12 119.7(3) . . ?
N1 C11 C16 121.4(3) . . ?
C12 C11 C16 118.8(3) . . ?
C1 C9 C10 119.6(3) . . ?
C1 C9 C8 122.7(3) . . ?
C10 C9 C8 117.7(4) . . ?
C2 C1 C9 119.8(3) . . ?
C2 C1 N1 120.4(4) . . ?
C9 C1 N1 119.7(3) . . ?
C5 C10 C4 121.9(4) . . ?
C5 C10 C9 119.5(4) . . ?
C4 C10 C9 118.6(4) . . ?
C1 C2 O1 118.1(3) . . ?
C1 C2 C3 120.7(4) . . ?
O1 C2 C3 121.2(4) . . ?
O3 N2 O2 121.8(5) . . ?
O3 N2 C14 118.7(5) . . ?
O2 N2 C14 119.5(5) . . ?
C15 C16 C11 120.1(4) . . ?
C15 C16 H16 119.9 . . ?
C11 C16 H16 119.9 . . ?
C13 C12 C11 120.9(4) . . ?
C13 C12 H12 119.5 . . ?
C11 C12 H12 119.5 . . ?
C3 C4 C10 120.9(4) . . ?
C3 C4 H4 119.5 . . ?
C10 C4 H4 119.5 . . ?
C7 C8 C9 121.4(4) . . ?
C7 C8 H8 119.3 . . ?
C9 C8 H8 119.3 . . ?
C15 C14 C13 120.8(4) . . ?
C15 C14 N2 119.8(5) . . ?
C13 C14 N2 119.4(4) . . ?
C4 C3 C2 120.3(4) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C12 C13 C14 118.8(4) . . ?
C12 C13 H13 120.6 . . ?
C14 C13 H13 120.6 . . ?
C6 C5 C10 121.1(4) . . ?
C6 C5 H5 119.5 . . ?
C10 C5 H5 119.5 . . ?
C8 C7 C6 120.7(4) . . ?
C8 C7 H7 119.6 . . ?
C6 C7 H7 119.6 . . ?
C14 C15 C16 120.5(4) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 H15 119.8 . . ?
C5 C6 C7 119.6(4) . . ?
C5 C6 H6 120.2 . . ?
C7 C6 H6 120.2 . . ?

_refine_diff_density_max         0.242
_refine_diff_density_min         -0.225
_refine_diff_density_rms         0.060

_shelxl_version_number           2013-4

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_h-m   ?
_symmetry_int_tables_number      ?
_chemical_absolute_configuration ?

####################################################################### 
# 
# 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_shelx_CCDC3
_database_code_depnum_ccdc_archive 'CCDC 1866319'
_audit_update_record             
;
2018-09-06 deposited with the CCDC.
2018-11-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H9 N O2'
_chemical_formula_sum            'C16 H9 N O2'
_chemical_formula_weight         247.24

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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_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+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   3.9089(13)
_cell_length_b                   23.323(8)
_cell_length_c                   12.350(4)
_cell_angle_alpha                90
_cell_angle_beta                 94.388(4)
_cell_angle_gamma                90
_cell_volume                     1122.6(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    23451
_cell_measurement_theta_min      1.746
_cell_measurement_theta_max      24.997

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.463
_exptl_crystal_F_000             512
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.34
_exptl_crystal_size_min          0.32
_exptl_absorpt_coefficient_mu    0.098
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   MULTI-SCAN
_exptl_absorpt_correction_T_min  0.965
_exptl_absorpt_correction_T_max  0.969
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            25762
_diffrn_reflns_av_unetI/netI     0.0204
_diffrn_reflns_av_R_equivalents  0.0584
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       4
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.746
_diffrn_reflns_theta_max         24.997
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 0.975
_reflns_number_total             1987
_reflns_number_gt                1531
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXL-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_refine_special_details          
;
 ?
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0416P)²+0.4670P] 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         1987
_refine_ls_number_parameters     172
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0587
_refine_ls_R_factor_gt           0.0416
_refine_ls_wR_factor_ref         0.1112
_refine_ls_wR_factor_gt          0.0972
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.051
_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 0.6375(3) 0.51145(5) 0.36774(10) 0.0447(3) Uani 1 1 d . . . . .
N1 N 0.3928(4) 0.47004(6) 0.16200(12) 0.0398(4) Uani 1 1 d . . . . .
O2 O 1.1276(4) 0.33312(6) 0.44851(12) 0.0673(5) Uani 1 1 d . . . . .
C12 C 0.6453(4) 0.37804(7) 0.20119(14) 0.0361(4) Uani 1 1 d . . . . .
C7 C 0.5708(4) 0.43733(7) 0.22992(13) 0.0352(4) Uani 1 1 d . . . . .
C2 C 0.4500(4) 0.54664(8) 0.29596(14) 0.0380(4) Uani 1 1 d . . . . .
C8 C 0.7049(4) 0.45668(8) 0.33748(14) 0.0372(4) Uani 1 1 d . . . . .
C1 C 0.3299(4) 0.52610(7) 0.19423(14) 0.0377(4) Uani 1 1 d . . . . .
C11 C 0.8289(4) 0.34197(8) 0.27517(14) 0.0394(4) Uani 1 1 d . . . . .
C9 C 0.8899(5) 0.42316(8) 0.40785(15) 0.0434(5) Uani 1 1 d . . . . .
H9 H 0.9750 0.4383 0.4742 0.052 Uiso 1 1 calc R U . . .
C3 C 0.3900(5) 0.60180(8) 0.32845(16) 0.0448(5) Uani 1 1 d . . . . .
H3 H 0.4726 0.6146 0.3968 0.054 Uiso 1 1 calc R U . . .
C13 C 0.5321(5) 0.35658(8) 0.09915(15) 0.0446(5) Uani 1 1 d . . . . .
H13 H 0.4108 0.3802 0.0491 0.053 Uiso 1 1 calc R U . . .
C6 C 0.1441(5) 0.56325(8) 0.12406(16) 0.0464(5) Uani 1 1 d . . . . .
H6 H 0.0608 0.5506 0.0557 0.056 Uiso 1 1 calc R U . . .
C10 C 0.9604(5) 0.36415(8) 0.38328(15) 0.0457(5) Uani 1 1 d . . . . .
C16 C 0.8926(5) 0.28583(8) 0.24634(16) 0.0483(5) Uani 1 1 d . . . . .
H16 H 1.0134 0.2618 0.2957 0.058 Uiso 1 1 calc R U . . .
C5 C 0.0831(5) 0.61853(8) 0.15528(17) 0.0498(5) Uani 1 1 d . . . . .
H5 H -0.0400 0.6433 0.1078 0.060 Uiso 1 1 calc R U . . .
C4 C 0.2045(5) 0.63768(8) 0.25754(17) 0.0475(5) Uani 1 1 d . . . . .
H4 H 0.1602 0.6751 0.2783 0.057 Uiso 1 1 calc R U . . .
C15 C 0.7791(5) 0.26516(8) 0.14531(17) 0.0496(5) Uani 1 1 d . . . . .
H15 H 0.8237 0.2274 0.1266 0.059 Uiso 1 1 calc R U . . .
C14 C 0.5992(5) 0.30070(9) 0.07225(16) 0.0501(5) Uani 1 1 d . . . . .
H14 H 0.5224 0.2868 0.0041 0.060 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 C8 1.362(2) . ?
O1 C2 1.377(2) . ?
N1 C7 1.296(2) . ?
N1 C1 1.394(2) . ?
O2 C10 1.233(2) . ?
C12 C11 1.399(2) . ?
C12 C13 1.396(2) . ?
C12 C7 1.463(2) . ?
C7 C8 1.462(2) . ?
C2 C3 1.373(3) . ?
C2 C1 1.392(2) . ?
C8 C9 1.339(2) . ?
C1 C6 1.390(2) . ?
C11 C16 1.384(3) . ?
C11 C10 1.486(3) . ?
C9 C10 1.440(3) . ?
C9 H9 0.9300 . ?
C3 C4 1.377(3) . ?
C3 H3 0.9300 . ?
C13 C14 1.375(3) . ?
C13 H13 0.9300 . ?
C6 C5 1.372(3) . ?
C6 H6 0.9300 . ?
C16 C15 1.379(3) . ?
C16 H16 0.9300 . ?
C5 C4 1.389(3) . ?
C5 H5 0.9300 . ?
C4 H4 0.9300 . ?
C15 C14 1.378(3) . ?
C15 H15 0.9300 . ?
C14 H14 0.9300 . ?

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
C8 O1 C2 119.12(14) . . ?
C7 N1 C1 117.69(15) . . ?
C11 C12 C13 119.03(17) . . ?
C11 C12 C7 120.78(16) . . ?
C13 C12 C7 120.19(16) . . ?
N1 C7 C8 122.95(16) . . ?
N1 C7 C12 120.42(15) . . ?
C8 C7 C12 116.63(15) . . ?
C3 C2 O1 117.69(16) . . ?
C3 C2 C1 122.18(17) . . ?
O1 C2 C1 120.13(16) . . ?
C9 C8 O1 118.39(16) . . ?
C9 C8 C7 123.23(17) . . ?
O1 C8 C7 118.38(15) . . ?
C6 C1 C2 118.18(17) . . ?
C6 C1 N1 120.11(16) . . ?
C2 C1 N1 121.71(16) . . ?
C16 C11 C12 119.61(17) . . ?
C16 C11 C10 120.24(17) . . ?
C12 C11 C10 120.14(17) . . ?
C8 C9 C10 121.57(17) . . ?
C8 C9 H9 119.2 . . ?
C10 C9 H9 119.2 . . ?
C2 C3 C4 118.50(18) . . ?
C2 C3 H3 120.8 . . ?
C4 C3 H3 120.8 . . ?
C14 C13 C12 120.31(18) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C5 C6 C1 120.28(18) . . ?
C5 C6 H6 119.9 . . ?
C1 C6 H6 119.9 . . ?
O2 C10 C9 121.57(18) . . ?
O2 C10 C11 120.83(18) . . ?
C9 C10 C11 117.59(16) . . ?
C15 C16 C11 120.77(18) . . ?
C15 C16 H16 119.6 . . ?
C11 C16 H16 119.6 . . ?
C6 C5 C4 120.22(19) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C3 C4 C5 120.64(19) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
C14 C15 C16 119.67(19) . . ?
C14 C15 H15 120.2 . . ?
C16 C15 H15 120.2 . . ?
C13 C14 C15 120.61(18) . . ?
C13 C14 H14 119.7 . . ?
C15 C14 H14 119.7 . . ?

_refine_diff_density_max         0.146
_refine_diff_density_min         -0.164
_refine_diff_density_rms         0.034

_shelxl_version_number           2013-4

