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

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

data_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1530737'
_audit_update_record             
;
2017-02-02 deposited with the CCDC.
2017-03-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H13 N O3'
_chemical_formula_weight         255.26
_chemical_absolute_configuration unk

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   'C c'

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

_cell_length_a                   4.0145(3)
_cell_length_b                   26.7097(18)
_cell_length_c                   11.7285(10)
_cell_angle_alpha                90.00
_cell_angle_beta                 94.126(7)
_cell_angle_gamma                90.00
_cell_volume                     1254.34(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    290(2)
_cell_measurement_reflns_used    798
_cell_measurement_theta_min      3.5059
_cell_measurement_theta_max      28.9171

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.32
_exptl_crystal_size_min          0.23
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.352
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             536
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9675
_exptl_absorpt_correction_T_max  0.9785
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      290(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Gemini S Ultra, Agilent Technologies'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 15.9149
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            2971
_diffrn_reflns_av_R_equivalents  0.0179
_diffrn_reflns_av_sigmaI/netI    0.0357
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       3
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.51
_diffrn_reflns_theta_max         26.37
_reflns_number_total             1852
_reflns_number_gt                1427
_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, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 (L. J. Farrugia, 2001)'
_computing_publication_material  SHELXL-97

_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)+(0.0375P)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   ?
_refine_ls_number_reflns         1852
_refine_ls_number_parameters     180
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0573
_refine_ls_R_factor_gt           0.0396
_refine_ls_wR_factor_ref         0.0842
_refine_ls_wR_factor_gt          0.0754
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_restrained_S_all      1.013
_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
O3 O -0.1784(5) 0.08876(6) 0.35301(16) 0.0572(5) Uani 1 1 d . . .
O2 O 0.4123(5) 0.05736(7) 0.86257(16) 0.0584(5) Uani 1 1 d D . .
O1 O 0.4390(5) 0.09713(7) 1.05432(18) 0.0627(6) Uani 1 1 d D . .
N1 N -0.0040(5) 0.21266(8) 1.0429(2) 0.0557(6) Uani 1 1 d . . .
C12 C -0.0695(5) 0.08805(9) 0.4655(2) 0.0436(7) Uani 1 1 d . . .
C7 C 0.1530(6) 0.13389(9) 0.8941(2) 0.0455(7) Uani 1 1 d . . .
H7 H 0.0259 0.1606 0.8643 0.055 Uiso 1 1 calc R . .
C5 C 0.1739(6) 0.17418(9) 1.0884(2) 0.0459(6) Uani 1 1 d . . .
C9 C 0.1275(6) 0.09268(9) 0.6990(2) 0.0411(6) Uani 1 1 d . . .
C6 C 0.2593(6) 0.13353(9) 1.0088(2) 0.0455(6) Uani 1 1 d . . .
C11 C -0.1554(6) 0.12869(10) 0.5299(2) 0.0497(7) Uani 1 1 d . . .
H11 H -0.2781 0.1547 0.4950 0.060 Uiso 1 1 calc R . .
C13 C 0.1178(6) 0.04913(10) 0.5170(2) 0.0484(7) Uani 1 1 d . . .
H13 H 0.1777 0.0216 0.4744 0.058 Uiso 1 1 calc R . .
C15 C -0.0746(7) 0.04930(11) 0.2817(2) 0.0589(7) Uani 1 1 d . . .
H15A H -0.1574 0.0555 0.2041 0.088 Uiso 1 1 calc R . .
H15C H -0.1616 0.0180 0.3069 0.088 Uiso 1 1 calc R . .
H15B H 0.1649 0.0478 0.2859 0.088 Uiso 1 1 calc R . .
C14 C 0.2132(6) 0.05218(9) 0.6328(2) 0.0478(7) Uani 1 1 d . . .
H14 H 0.3385 0.0263 0.6672 0.057 Uiso 1 1 calc R . .
C1 C -0.0803(8) 0.24897(11) 1.1138(3) 0.0640(8) Uani 1 1 d . . .
H1A H -0.2038 0.2759 1.0834 0.077 Uiso 1 1 calc R . .
C3 C 0.1911(7) 0.20979(12) 1.2748(3) 0.0642(8) Uani 1 1 d . . .
H3 H 0.2554 0.2088 1.3525 0.077 Uiso 1 1 calc R . .
C2 C 0.0112(8) 0.24938(11) 1.2293(3) 0.0640(8) Uani 1 1 d . . .
H2A H -0.0480 0.2759 1.2751 0.077 Uiso 1 1 calc R . .
C8 C 0.2344(5) 0.09449(9) 0.8223(2) 0.0437(6) Uani 1 1 d . . .
C4 C 0.2761(7) 0.17142(10) 1.2041(2) 0.0560(7) Uani 1 1 d . . .
H4 H 0.3993 0.1442 1.2331 0.067 Uiso 1 1 calc R . .
C10 C -0.0620(6) 0.13116(9) 0.6445(2) 0.0473(7) Uani 1 1 d . . .
H10 H -0.1249 0.1586 0.6866 0.057 Uiso 1 1 calc R . .
H2 H 0.500(15) 0.068(2) 0.926(3) 0.071 Uiso 0.54(5) 1 d PD A 2
H1 H 0.434(17) 0.074(2) 1.003(5) 0.071 Uiso 0.46(5) 1 d PD A 1

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O3 0.0670(11) 0.0585(12) 0.0453(11) -0.0016(9) -0.0016(9) 0.0097(9)
O2 0.0751(14) 0.0486(11) 0.0500(12) 0.0016(11) -0.0050(10) 0.0137(10)
O1 0.0842(15) 0.0532(13) 0.0493(13) 0.0016(9) -0.0052(10) 0.0183(10)
N1 0.0646(15) 0.0496(15) 0.0530(14) -0.0026(12) 0.0051(11) 0.0025(12)
C12 0.0425(15) 0.0456(17) 0.0423(16) 0.0026(12) 0.0004(12) -0.0040(11)
C7 0.0524(18) 0.0405(15) 0.0435(17) 0.0033(12) 0.0031(13) 0.0017(12)
C5 0.0476(15) 0.0416(16) 0.0486(16) 0.0013(12) 0.0053(12) -0.0058(12)
C9 0.0409(14) 0.0408(14) 0.0424(14) 0.0028(11) 0.0076(11) -0.0046(11)
C6 0.0448(16) 0.0421(15) 0.0500(17) 0.0004(12) 0.0058(13) -0.0039(12)
C11 0.0559(17) 0.0445(16) 0.0485(17) 0.0037(13) 0.0034(14) 0.0110(12)
C13 0.0524(18) 0.0458(16) 0.0473(16) -0.0043(12) 0.0055(13) 0.0074(12)
C15 0.0667(19) 0.0642(18) 0.0451(15) -0.0040(14) 0.0000(13) 0.0008(15)
C14 0.0534(17) 0.0413(15) 0.0484(16) 0.0046(13) 0.0022(13) 0.0083(12)
C1 0.074(2) 0.0483(17) 0.071(2) -0.0003(15) 0.0134(17) 0.0050(14)
C3 0.076(2) 0.069(2) 0.0475(17) -0.0068(16) 0.0055(15) -0.0081(17)
C2 0.073(2) 0.0544(18) 0.066(2) -0.0137(16) 0.0186(16) -0.0111(16)
C8 0.0445(17) 0.0403(15) 0.0461(16) 0.0052(12) 0.0015(13) -0.0031(11)
C4 0.0619(18) 0.0579(18) 0.0477(17) 0.0000(14) 0.0008(14) -0.0046(14)
C10 0.0539(17) 0.0379(14) 0.0500(18) -0.0027(12) 0.0040(14) 0.0051(11)

_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
O3 C12 1.360(3) . ?
O3 C15 1.426(3) . ?
O2 C8 1.291(3) . ?
O2 H2 0.85(2) . ?
O1 C6 1.302(3) . ?
O1 H1 0.85(2) . ?
N1 C1 1.327(4) . ?
N1 C5 1.340(3) . ?
C12 C11 1.380(3) . ?
C12 C13 1.395(3) . ?
C7 C6 1.381(3) . ?
C7 C8 1.402(3) . ?
C7 H7 0.9300 . ?
C5 C4 1.390(3) . ?
C5 C6 1.489(3) . ?
C9 C14 1.389(3) . ?
C9 C10 1.405(3) . ?
C9 C8 1.479(3) . ?
C11 C10 1.370(3) . ?
C11 H11 0.9300 . ?
C13 C14 1.387(3) . ?
C13 H13 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15C 0.9600 . ?
C15 H15B 0.9600 . ?
C14 H14 0.9300 . ?
C1 C2 1.378(4) . ?
C1 H1A 0.9300 . ?
C3 C2 1.367(4) . ?
C3 C4 1.377(4) . ?
C3 H3 0.9300 . ?
C2 H2A 0.9300 . ?
C4 H4 0.9300 . ?
C10 H10 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
C12 O3 C15 118.2(2) . . ?
C8 O2 H2 105(4) . . ?
C6 O1 H1 105(5) . . ?
C1 N1 C5 116.8(2) . . ?
O3 C12 C11 116.4(2) . . ?
O3 C12 C13 123.8(2) . . ?
C11 C12 C13 119.8(2) . . ?
C6 C7 C8 120.7(2) . . ?
C6 C7 H7 119.6 . . ?
C8 C7 H7 119.6 . . ?
N1 C5 C4 122.7(3) . . ?
N1 C5 C6 116.7(2) . . ?
C4 C5 C6 120.6(2) . . ?
C14 C9 C10 117.6(2) . . ?
C14 C9 C8 120.4(2) . . ?
C10 C9 C8 122.1(2) . . ?
O1 C6 C7 121.9(2) . . ?
O1 C6 C5 115.7(2) . . ?
C7 C6 C5 122.5(2) . . ?
C10 C11 C12 120.8(2) . . ?
C10 C11 H11 119.6 . . ?
C12 C11 H11 119.6 . . ?
C14 C13 C12 118.8(2) . . ?
C14 C13 H13 120.6 . . ?
C12 C13 H13 120.6 . . ?
O3 C15 H15A 109.5 . . ?
O3 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
O3 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15C C15 H15B 109.5 . . ?
C13 C14 C9 122.1(2) . . ?
C13 C14 H14 119.0 . . ?
C9 C14 H14 119.0 . . ?
N1 C1 C2 124.3(3) . . ?
N1 C1 H1A 117.8 . . ?
C2 C1 H1A 117.8 . . ?
C2 C3 C4 119.2(3) . . ?
C2 C3 H3 120.4 . . ?
C4 C3 H3 120.4 . . ?
C3 C2 C1 118.2(3) . . ?
C3 C2 H2A 120.9 . . ?
C1 C2 H2A 120.9 . . ?
O2 C8 C7 120.2(2) . . ?
O2 C8 C9 116.5(2) . . ?
C7 C8 C9 123.2(2) . . ?
C3 C4 C5 118.7(3) . . ?
C3 C4 H4 120.7 . . ?
C5 C4 H4 120.7 . . ?
C11 C10 C9 120.8(2) . . ?
C11 C10 H10 119.6 . . ?
C9 C10 H10 119.6 . . ?

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
C15 O3 C12 C11 175.5(2) . . . . ?
C15 O3 C12 C13 -4.8(3) . . . . ?
C1 N1 C5 C4 0.2(4) . . . . ?
C1 N1 C5 C6 -180.0(2) . . . . ?
C8 C7 C6 O1 0.3(4) . . . . ?
C8 C7 C6 C5 -179.0(2) . . . . ?
N1 C5 C6 O1 178.4(2) . . . . ?
C4 C5 C6 O1 -1.7(4) . . . . ?
N1 C5 C6 C7 -2.2(3) . . . . ?
C4 C5 C6 C7 177.7(3) . . . . ?
O3 C12 C11 C10 179.0(2) . . . . ?
C13 C12 C11 C10 -0.7(4) . . . . ?
O3 C12 C13 C14 -179.5(2) . . . . ?
C11 C12 C13 C14 0.2(4) . . . . ?
C12 C13 C14 C9 0.1(4) . . . . ?
C10 C9 C14 C13 0.0(4) . . . . ?
C8 C9 C14 C13 -180.0(2) . . . . ?
C5 N1 C1 C2 0.0(4) . . . . ?
C4 C3 C2 C1 0.5(5) . . . . ?
N1 C1 C2 C3 -0.3(5) . . . . ?
C6 C7 C8 O2 -0.4(4) . . . . ?
C6 C7 C8 C9 179.9(2) . . . . ?
C14 C9 C8 O2 1.1(3) . . . . ?
C10 C9 C8 O2 -178.9(2) . . . . ?
C14 C9 C8 C7 -179.2(2) . . . . ?
C10 C9 C8 C7 0.8(3) . . . . ?
C2 C3 C4 C5 -0.3(4) . . . . ?
N1 C5 C4 C3 0.0(4) . . . . ?
C6 C5 C4 C3 -179.9(2) . . . . ?
C12 C11 C10 C9 0.9(4) . . . . ?
C14 C9 C10 C11 -0.5(4) . . . . ?
C8 C9 C10 C11 179.5(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2 O1 0.85(2) 1.73(4) 2.482(3) 147(6) .
O1 H1 O2 0.85(2) 1.71(4) 2.482(3) 150(8) .

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        26.37
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         0.093
_refine_diff_density_min         -0.138
_refine_diff_density_rms         0.032
####################################################################### 
# 
# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1530738'
_audit_update_record             
;
2017-02-02 deposited with the CCDC.
2017-03-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H13 N O3'
_chemical_formula_weight         255.26

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   C2/c

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

_cell_length_a                   21.986(2)
_cell_length_b                   3.9115(4)
_cell_length_c                   30.020(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 106.946(9)
_cell_angle_gamma                90.00
_cell_volume                     2469.6(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    290(2)
_cell_measurement_reflns_used    1330
_cell_measurement_theta_min      3.0752
_cell_measurement_theta_max      69.3854

_exptl_crystal_description       ?
_exptl_crystal_colour            off-white
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.373
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1072
_exptl_absorpt_coefficient_mu    0.791
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7973
_exptl_absorpt_correction_T_max  0.8578
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      290(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'Enhance Ultra (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'Gemini S Ultra, Agilent Technologies'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 15.9149
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3956
_diffrn_reflns_av_R_equivalents  0.0259
_diffrn_reflns_av_sigmaI/netI    0.0364
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -4
_diffrn_reflns_limit_k_max       4
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_theta_min         3.08
_diffrn_reflns_theta_max         65.07
_reflns_number_total             2096
_reflns_number_gt                1522
_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, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 (L. J. Farrugia, 2001)'
_computing_publication_material  SHELXL-97

_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)+(0.0878P)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    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2096
_refine_ls_number_parameters     174
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0738
_refine_ls_R_factor_gt           0.0575
_refine_ls_wR_factor_ref         0.1688
_refine_ls_wR_factor_gt          0.1491
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_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
O2 O 0.17590(8) 0.2239(6) 0.05451(5) 0.0816(6) Uani 1 1 d . . .
O3 O 0.45549(8) -0.3171(5) 0.09127(6) 0.0796(6) Uani 1 1 d . . .
O1 O 0.10350(7) 0.5035(6) 0.09248(5) 0.0809(6) Uani 1 1 d . . .
N1 N 0.16618(9) 0.8334(6) 0.25150(6) 0.0746(6) Uani 1 1 d . . .
C4 C 0.13283(10) 0.6397(6) 0.17198(7) 0.0559(5) Uani 1 1 d . . .
C6 C 0.14862(10) 0.4945(6) 0.13105(7) 0.0570(6) Uani 1 1 d . . .
C3 C 0.07032(11) 0.7245(7) 0.16877(8) 0.0693(7) Uani 1 1 d . . .
H3 H 0.0380 0.6887 0.1413 0.083 Uiso 1 1 calc R . .
C5 C 0.17829(10) 0.7015(7) 0.21394(7) 0.0652(7) Uani 1 1 d . . .
H5 H 0.2203 0.6473 0.2162 0.078 Uiso 1 1 calc R . .
C9 C 0.28178(10) 0.0781(6) 0.09378(7) 0.0537(5) Uani 1 1 d . . .
C13 C 0.34790(11) -0.1576(7) 0.04959(8) 0.0657(6) Uani 1 1 d . . .
H13 H 0.3528 -0.2255 0.0211 0.079 Uiso 1 1 calc R . .
C14 C 0.29045(11) -0.0221(7) 0.05183(8) 0.0647(6) Uani 1 1 d . . .
H14 H 0.2571 0.0018 0.0246 0.078 Uiso 1 1 calc R . .
C8 C 0.21960(10) 0.2229(6) 0.09361(7) 0.0574(5) Uani 1 1 d . . .
C1 C 0.10543(11) 0.9119(7) 0.24685(8) 0.0734(7) Uani 1 1 d . . .
H1A H 0.0956 1.0060 0.2724 0.088 Uiso 1 1 calc R . .
C7 C 0.20780(10) 0.3569(6) 0.13372(7) 0.0561(6) Uani 1 1 d . . .
H7 H 0.2396 0.3534 0.1620 0.067 Uiso 1 1 calc R . .
C11 C 0.38944(11) -0.0927(7) 0.13200(8) 0.0670(7) Uani 1 1 d . . .
H11 H 0.4229 -0.1165 0.1592 0.080 Uiso 1 1 calc R . .
C10 C 0.33184(10) 0.0403(7) 0.13376(7) 0.0632(6) Uani 1 1 d . . .
H10 H 0.3268 0.1050 0.1623 0.076 Uiso 1 1 calc R . .
C12 C 0.39697(10) -0.1904(6) 0.08939(7) 0.0601(6) Uani 1 1 d . . .
C2 C 0.05732(12) 0.8628(8) 0.20727(8) 0.0752(7) Uani 1 1 d . . .
H2A H 0.0159 0.9218 0.2061 0.090 Uiso 1 1 calc R . .
C15 C 0.46619(12) -0.4246(8) 0.04852(9) 0.0812(8) Uani 1 1 d . . .
H15A H 0.4616 -0.2323 0.0279 0.122 Uiso 1 1 calc R . .
H15B H 0.4358 -0.5972 0.0342 0.122 Uiso 1 1 calc R . .
H15C H 0.5084 -0.5160 0.0548 0.122 Uiso 1 1 calc R . .
H2 H 0.1438 0.3118 0.0577 0.122 Uiso 0.46(5) 1 d PR A 2
H1 H 0.1159 0.4221 0.0717 0.122 Uiso 0.54(5) 1 d PR A 1

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O2 0.0632(9) 0.1238(17) 0.0548(9) -0.0137(9) 0.0128(7) 0.0156(10)
O3 0.0605(9) 0.1075(15) 0.0758(10) -0.0066(10) 0.0275(8) 0.0105(9)
O1 0.0571(9) 0.1229(17) 0.0593(9) -0.0105(10) 0.0114(8) 0.0171(10)
N1 0.0648(12) 0.1043(18) 0.0573(11) -0.0098(11) 0.0217(9) 0.0041(11)
C4 0.0527(11) 0.0633(13) 0.0546(11) 0.0058(10) 0.0203(9) 0.0002(10)
C6 0.0551(11) 0.0645(14) 0.0523(11) 0.0020(10) 0.0173(9) -0.0017(10)
C3 0.0530(12) 0.0919(18) 0.0624(13) 0.0020(13) 0.0159(10) 0.0067(12)
C5 0.0529(11) 0.0878(18) 0.0578(12) -0.0036(12) 0.0204(10) 0.0038(11)
C9 0.0563(11) 0.0559(12) 0.0524(11) -0.0014(10) 0.0211(9) -0.0030(10)
C13 0.0690(14) 0.0759(16) 0.0577(12) -0.0085(11) 0.0272(11) 0.0029(12)
C14 0.0611(12) 0.0789(16) 0.0538(12) -0.0075(11) 0.0163(10) 0.0030(12)
C8 0.0554(11) 0.0631(14) 0.0547(11) -0.0011(10) 0.0173(9) -0.0025(10)
C1 0.0715(14) 0.094(2) 0.0624(13) -0.0029(13) 0.0319(11) 0.0100(14)
C7 0.0533(11) 0.0669(14) 0.0485(10) -0.0014(10) 0.0153(9) 0.0003(10)
C11 0.0565(12) 0.0883(18) 0.0560(12) -0.0006(12) 0.0162(10) 0.0038(12)
C10 0.0623(12) 0.0791(16) 0.0517(11) -0.0018(11) 0.0219(10) 0.0011(12)
C12 0.0545(11) 0.0660(14) 0.0639(12) -0.0011(11) 0.0239(10) 0.0001(11)
C2 0.0608(13) 0.099(2) 0.0719(14) -0.0008(14) 0.0285(12) 0.0126(13)
C15 0.0744(15) 0.093(2) 0.0864(17) -0.0143(15) 0.0389(14) 0.0085(14)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 C8 1.282(2) . ?
O2 H2 0.8153 . ?
O3 C12 1.365(3) . ?
O3 C15 1.433(3) . ?
O1 C6 1.287(2) . ?
O1 H1 0.8163 . ?
N1 C5 1.335(3) . ?
N1 C1 1.338(3) . ?
C4 C5 1.382(3) . ?
C4 C3 1.390(3) . ?
C4 C6 1.484(3) . ?
C6 C7 1.389(3) . ?
C3 C2 1.379(3) . ?
C3 H3 0.9300 . ?
C5 H5 0.9300 . ?
C9 C10 1.380(3) . ?
C9 C14 1.384(3) . ?
C9 C8 1.478(3) . ?
C13 C12 1.362(3) . ?
C13 C14 1.390(3) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C8 C7 1.405(3) . ?
C1 C2 1.354(3) . ?
C1 H1A 0.9300 . ?
C7 H7 0.9300 . ?
C11 C10 1.384(3) . ?
C11 C12 1.391(3) . ?
C11 H11 0.9300 . ?
C10 H10 0.9300 . ?
C2 H2A 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 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
C8 O2 H2 109.7 . . ?
C12 O3 C15 117.92(19) . . ?
C6 O1 H1 109.6 . . ?
C5 N1 C1 116.1(2) . . ?
C5 C4 C3 117.3(2) . . ?
C5 C4 C6 122.70(18) . . ?
C3 C4 C6 119.96(19) . . ?
O1 C6 C7 121.75(19) . . ?
O1 C6 C4 115.43(18) . . ?
C7 C6 C4 122.82(18) . . ?
C2 C3 C4 118.5(2) . . ?
C2 C3 H3 120.7 . . ?
C4 C3 H3 120.7 . . ?
N1 C5 C4 124.6(2) . . ?
N1 C5 H5 117.7 . . ?
C4 C5 H5 117.7 . . ?
C10 C9 C14 118.3(2) . . ?
C10 C9 C8 123.13(19) . . ?
C14 C9 C8 118.53(19) . . ?
C12 C13 C14 119.5(2) . . ?
C12 C13 H13 120.3 . . ?
C14 C13 H13 120.3 . . ?
C9 C14 C13 121.4(2) . . ?
C9 C14 H14 119.3 . . ?
C13 C14 H14 119.3 . . ?
O2 C8 C7 120.5(2) . . ?
O2 C8 C9 116.74(19) . . ?
C7 C8 C9 122.78(19) . . ?
N1 C1 C2 124.0(2) . . ?
N1 C1 H1A 118.0 . . ?
C2 C1 H1A 118.0 . . ?
C6 C7 C8 119.93(19) . . ?
C6 C7 H7 120.0 . . ?
C8 C7 H7 120.0 . . ?
C10 C11 C12 119.6(2) . . ?
C10 C11 H11 120.2 . . ?
C12 C11 H11 120.2 . . ?
C9 C10 C11 120.9(2) . . ?
C9 C10 H10 119.5 . . ?
C11 C10 H10 119.5 . . ?
C13 C12 O3 124.5(2) . . ?
C13 C12 C11 120.3(2) . . ?
O3 C12 C11 115.2(2) . . ?
C1 C2 C3 119.4(2) . . ?
C1 C2 H2A 120.3 . . ?
C3 C2 H2A 120.3 . . ?
O3 C15 H15A 109.5 . . ?
O3 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
O3 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 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
C5 C4 C6 O1 -169.1(2) . . . . ?
C3 C4 C6 O1 9.9(3) . . . . ?
C5 C4 C6 C7 11.0(4) . . . . ?
C3 C4 C6 C7 -170.0(2) . . . . ?
C5 C4 C3 C2 -0.2(4) . . . . ?
C6 C4 C3 C2 -179.2(2) . . . . ?
C1 N1 C5 C4 -0.7(4) . . . . ?
C3 C4 C5 N1 0.6(4) . . . . ?
C6 C4 C5 N1 179.6(2) . . . . ?
C10 C9 C14 C13 0.0(4) . . . . ?
C8 C9 C14 C13 179.5(2) . . . . ?
C12 C13 C14 C9 -0.5(4) . . . . ?
C10 C9 C8 O2 -175.7(2) . . . . ?
C14 C9 C8 O2 4.8(3) . . . . ?
C10 C9 C8 C7 4.7(4) . . . . ?
C14 C9 C8 C7 -174.8(2) . . . . ?
C5 N1 C1 C2 0.5(4) . . . . ?
O1 C6 C7 C8 0.0(4) . . . . ?
C4 C6 C7 C8 179.9(2) . . . . ?
O2 C8 C7 C6 -0.6(4) . . . . ?
C9 C8 C7 C6 178.9(2) . . . . ?
C14 C9 C10 C11 0.4(4) . . . . ?
C8 C9 C10 C11 -179.1(2) . . . . ?
C12 C11 C10 C9 -0.2(4) . . . . ?
C14 C13 C12 O3 -179.4(2) . . . . ?
C14 C13 C12 C11 0.7(4) . . . . ?
C15 O3 C12 C13 -0.2(4) . . . . ?
C15 O3 C12 C11 179.6(2) . . . . ?
C10 C11 C12 C13 -0.4(4) . . . . ?
C10 C11 C12 O3 179.8(2) . . . . ?
N1 C1 C2 C3 -0.2(5) . . . . ?
C4 C3 C2 C1 0.0(4) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2 O1 0.82 1.73 2.467(2) 150.4 .
O1 H1 O2 0.82 1.73 2.467(2) 148.9 .

_diffrn_measured_fraction_theta_max 0.989
_diffrn_reflns_theta_full        65.07
_diffrn_measured_fraction_theta_full 0.989
_refine_diff_density_max         0.192
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.045
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_exptl_crystal_preparation       ', Luminescent'
####################################################################### 
# 
# 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_shelxl
_database_code_depnum_ccdc_archive 'CCDC 1530739'
_audit_update_record             
;
2017-02-02 deposited with the CCDC.
2017-03-20 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H13 N O3'
_chemical_formula_weight         255.26
_chemical_absolute_configuration unk

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'

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

_cell_length_a                   3.8841(2)
_cell_length_b                   11.6062(6)
_cell_length_c                   27.6220(12)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1245.19(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    290(2)
_cell_measurement_reflns_used    2200
_cell_measurement_theta_min      3.1972
_cell_measurement_theta_max      69.3666

_exptl_crystal_description       ?
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.362
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             536
_exptl_absorpt_coefficient_mu    0.784
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7708
_exptl_absorpt_correction_T_max  0.8589
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.21 (release 14-08-2012 CrysAlis171 .NET)
(compiled Sep 14 2012,17:21:16)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      290(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'Enhance Ultra (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'Gemini S Ultra, Agilent Technologies'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 15.9149
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4321
_diffrn_reflns_av_R_equivalents  0.0257
_diffrn_reflns_av_sigmaI/netI    0.0308
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_h_max       2
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         3.20
_diffrn_reflns_theta_max         69.49
_reflns_number_total             2278
_reflns_number_gt                2025
_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, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Ortep-3 (L. J. Farrugia, 2001)'
_computing_publication_material  SHELXL-97

_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)+(0.0620P)²+0.0308P] 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       0.0054(11)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.0(3)
_refine_ls_number_reflns         2278
_refine_ls_number_parameters     181
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0454
_refine_ls_R_factor_gt           0.0404
_refine_ls_wR_factor_ref         0.1139
_refine_ls_wR_factor_gt          0.1083
_refine_ls_goodness_of_fit_ref   1.077
_refine_ls_restrained_S_all      1.077
_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
O2 O 0.6899(5) 1.02420(12) 0.05880(5) 0.0680(5) Uani 1 1 d D . .
O3 O 0.7640(5) 1.56060(12) 0.08896(5) 0.0758(5) Uani 1 1 d . . .
O1 O 0.4822(6) 0.84547(13) 0.09647(5) 0.0787(5) Uani 1 1 d D . .
C3 C 0.2535(5) 0.83745(16) 0.17524(6) 0.0529(4) Uani 1 1 d . . .
C9 C 0.6533(5) 1.20609(16) 0.09576(6) 0.0468(4) Uani 1 1 d . . .
N1 N -0.0096(7) 0.70383(16) 0.25146(7) 0.0739(5) Uani 1 1 d . . .
C7 C 0.4544(5) 1.02161(16) 0.13668(6) 0.0519(4) Uani 1 1 d . . .
H7 H 0.3936 1.0623 0.1644 0.062 Uiso 1 1 calc R . .
C8 C 0.6020(5) 1.08084(17) 0.09642(6) 0.0499(4) Uani 1 1 d . . .
C11 C 0.5933(6) 1.39537(18) 0.13000(6) 0.0604(5) Uani 1 1 d . . .
H11 H 0.5233 1.4425 0.1554 0.073 Uiso 1 1 calc R . .
C14 C 0.8036(5) 1.25671(16) 0.05497(6) 0.0503(4) Uani 1 1 d . . .
H14 H 0.8778 1.2097 0.0298 0.060 Uiso 1 1 calc R . .
C6 C 0.4024(5) 0.90588(16) 0.13464(6) 0.0529(5) Uani 1 1 d . . .
C10 C 0.5528(6) 1.27799(17) 0.13354(6) 0.0555(5) Uani 1 1 d . . .
H10 H 0.4574 1.2464 0.1614 0.067 Uiso 1 1 calc R . .
C12 C 0.7383(5) 1.44417(17) 0.08874(6) 0.0554(5) Uani 1 1 d . . .
C13 C 0.8447(5) 1.37396(17) 0.05111(6) 0.0536(5) Uani 1 1 d . . .
H13 H 0.9431 1.4058 0.0235 0.064 Uiso 1 1 calc R . .
C5 C 0.0019(7) 0.8173(2) 0.25338(7) 0.0661(5) Uani 1 1 d . . .
H5 H -0.0816 0.8527 0.2812 0.079 Uiso 1 1 calc R . .
C4 C 0.1282(6) 0.88736(18) 0.21724(6) 0.0596(5) Uani 1 1 d . . .
H4 H 0.1294 0.9670 0.2210 0.071 Uiso 1 1 calc R . .
C15 C 0.9048(8) 1.6161(2) 0.04731(9) 0.0831(8) Uani 1 1 d . . .
H15A H 0.7588 1.6021 0.0199 0.125 Uiso 1 1 calc R . .
H15B H 1.1305 1.5860 0.0409 0.125 Uiso 1 1 calc R . .
H15C H 0.9196 1.6975 0.0531 0.125 Uiso 1 1 calc R . .
C2 C 0.2450(8) 0.71945(17) 0.17227(8) 0.0734(7) Uani 1 1 d . . .
H2A H 0.3280 0.6817 0.1450 0.088 Uiso 1 1 calc R . .
C1 C 0.1104(9) 0.6578(2) 0.21078(8) 0.0863(9) Uani 1 1 d . . .
H1A H 0.1033 0.5780 0.2080 0.104 Uiso 1 1 calc R . .
H1 H 0.57(2) 0.898(5) 0.080(2) 0.129 Uiso 0.55(5) 1 d PD A 2
H2 H 0.64(3) 0.955(3) 0.065(3) 0.129 Uiso 0.45(5) 1 d PD A 1

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O2 0.1011(12) 0.0607(8) 0.0422(6) -0.0027(6) 0.0152(7) -0.0005(8)
O3 0.1011(13) 0.0577(8) 0.0686(9) -0.0041(7) 0.0216(9) -0.0065(8)
O1 0.1260(15) 0.0597(8) 0.0503(7) -0.0055(7) 0.0232(9) -0.0045(10)
C3 0.0578(11) 0.0599(9) 0.0410(8) 0.0014(7) -0.0014(8) -0.0004(9)
C9 0.0452(9) 0.0593(10) 0.0358(8) 0.0011(7) -0.0012(7) 0.0002(8)
N1 0.0923(14) 0.0712(11) 0.0582(9) 0.0089(8) 0.0129(10) -0.0077(11)
C7 0.0602(11) 0.0587(10) 0.0369(8) -0.0013(7) 0.0027(8) 0.0006(9)
C8 0.0521(10) 0.0600(10) 0.0376(8) 0.0003(7) -0.0011(8) 0.0036(8)
C11 0.0711(13) 0.0658(11) 0.0444(9) -0.0078(8) 0.0112(9) 0.0001(10)
C14 0.0538(10) 0.0605(10) 0.0366(7) -0.0040(8) 0.0031(8) -0.0020(8)
C6 0.0594(11) 0.0591(10) 0.0401(8) -0.0001(8) 0.0024(8) 0.0028(9)
C10 0.0632(12) 0.0633(10) 0.0399(8) -0.0001(8) 0.0095(8) -0.0011(10)
C12 0.0576(11) 0.0580(10) 0.0507(9) -0.0016(8) 0.0040(9) -0.0023(9)
C13 0.0549(11) 0.0642(11) 0.0416(8) 0.0025(8) 0.0036(8) -0.0052(9)
C5 0.0744(13) 0.0762(13) 0.0476(9) 0.0022(9) 0.0098(10) -0.0012(12)
C4 0.0705(13) 0.0598(10) 0.0483(9) -0.0009(8) 0.0099(9) -0.0017(10)
C15 0.100(2) 0.0628(12) 0.0865(15) 0.0042(12) 0.0287(16) -0.0084(13)
C2 0.1046(19) 0.0585(10) 0.0573(11) -0.0029(9) 0.0188(13) -0.0043(13)
C1 0.130(3) 0.0580(12) 0.0709(13) 0.0053(11) 0.0249(15) -0.0080(15)

_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
O2 C8 1.276(2) . ?
O2 H2 0.84(2) . ?
O3 C12 1.355(2) . ?
O3 C15 1.427(3) . ?
O1 C6 1.303(2) . ?
O1 H1 0.84(2) . ?
C3 C2 1.372(3) . ?
C3 C4 1.385(2) . ?
C3 C6 1.491(2) . ?
C9 C10 1.392(2) . ?
C9 C14 1.398(2) . ?
C9 C8 1.467(2) . ?
N1 C5 1.319(3) . ?
N1 C1 1.328(3) . ?
C7 C6 1.359(3) . ?
C7 C8 1.428(2) . ?
C7 H7 0.9300 . ?
C11 C10 1.375(3) . ?
C11 C12 1.392(3) . ?
C11 H11 0.9300 . ?
C14 C13 1.374(3) . ?
C14 H14 0.9300 . ?
C10 H10 0.9300 . ?
C12 C13 1.384(3) . ?
C13 H13 0.9300 . ?
C5 C4 1.377(3) . ?
C5 H5 0.9300 . ?
C4 H4 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C2 C1 1.384(3) . ?
C2 H2A 0.9300 . ?
C1 H1A 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 O2 H2 105(6) . . ?
C12 O3 C15 118.33(16) . . ?
C6 O1 H1 99(5) . . ?
C2 C3 C4 117.32(18) . . ?
C2 C3 C6 119.73(18) . . ?
C4 C3 C6 122.92(16) . . ?
C10 C9 C14 117.98(17) . . ?
C10 C9 C8 123.14(16) . . ?
C14 C9 C8 118.87(15) . . ?
C5 N1 C1 115.05(18) . . ?
C6 C7 C8 120.20(16) . . ?
C6 C7 H7 119.9 . . ?
C8 C7 H7 119.9 . . ?
O2 C8 C7 119.58(17) . . ?
O2 C8 C9 117.64(16) . . ?
C7 C8 C9 122.76(16) . . ?
C10 C11 C12 120.51(17) . . ?
C10 C11 H11 119.7 . . ?
C12 C11 H11 119.7 . . ?
C13 C14 C9 121.80(17) . . ?
C13 C14 H14 119.1 . . ?
C9 C14 H14 119.1 . . ?
O1 C6 C7 121.99(17) . . ?
O1 C6 C3 114.46(16) . . ?
C7 C6 C3 123.55(16) . . ?
C11 C10 C9 120.58(17) . . ?
C11 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
O3 C12 C13 124.65(17) . . ?
O3 C12 C11 115.58(17) . . ?
C13 C12 C11 119.76(17) . . ?
C14 C13 C12 119.34(17) . . ?
C14 C13 H13 120.3 . . ?
C12 C13 H13 120.3 . . ?
N1 C5 C4 124.90(19) . . ?
N1 C5 H5 117.6 . . ?
C4 C5 H5 117.6 . . ?
C5 C4 C3 119.03(18) . . ?
C5 C4 H4 120.5 . . ?
C3 C4 H4 120.5 . . ?
O3 C15 H15A 109.5 . . ?
O3 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
O3 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C3 C2 C1 118.6(2) . . ?
C3 C2 H2A 120.7 . . ?
C1 C2 H2A 120.7 . . ?
N1 C1 C2 125.1(2) . . ?
N1 C1 H1A 117.5 . . ?
C2 C1 H1A 117.5 . . ?

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
C6 C7 C8 O2 -1.1(3) . . . . ?
C6 C7 C8 C9 177.80(18) . . . . ?
C10 C9 C8 O2 176.84(19) . . . . ?
C14 C9 C8 O2 -1.8(3) . . . . ?
C10 C9 C8 C7 -2.1(3) . . . . ?
C14 C9 C8 C7 179.25(17) . . . . ?
C10 C9 C14 C13 -1.7(3) . . . . ?
C8 C9 C14 C13 177.01(18) . . . . ?
C8 C7 C6 O1 -0.3(3) . . . . ?
C8 C7 C6 C3 179.31(18) . . . . ?
C2 C3 C6 O1 6.9(3) . . . . ?
C4 C3 C6 O1 -174.8(2) . . . . ?
C2 C3 C6 C7 -172.8(2) . . . . ?
C4 C3 C6 C7 5.5(3) . . . . ?
C12 C11 C10 C9 -0.6(3) . . . . ?
C14 C9 C10 C11 1.6(3) . . . . ?
C8 C9 C10 C11 -177.0(2) . . . . ?
C15 O3 C12 C13 1.2(4) . . . . ?
C15 O3 C12 C11 -178.9(2) . . . . ?
C10 C11 C12 O3 179.6(2) . . . . ?
C10 C11 C12 C13 -0.4(3) . . . . ?
C9 C14 C13 C12 0.7(3) . . . . ?
O3 C12 C13 C14 -179.7(2) . . . . ?
C11 C12 C13 C14 0.4(3) . . . . ?
C1 N1 C5 C4 -0.5(4) . . . . ?
N1 C5 C4 C3 0.2(4) . . . . ?
C2 C3 C4 C5 -0.3(3) . . . . ?
C6 C3 C4 C5 -178.6(2) . . . . ?
C4 C3 C2 C1 0.6(4) . . . . ?
C6 C3 C2 C1 179.0(2) . . . . ?
C5 N1 C1 C2 0.9(5) . . . . ?
C3 C2 C1 N1 -1.0(5) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1 H1 O2 0.84(2) 1.64(3) 2.457(2) 163(8) .
O2 H2 O1 0.84(2) 1.66(4) 2.457(2) 158(9) .

_diffrn_measured_fraction_theta_max 0.982
_diffrn_reflns_theta_full        69.49
_diffrn_measured_fraction_theta_full 0.982
_refine_diff_density_max         0.166
_refine_diff_density_min         -0.120
_refine_diff_density_rms         0.031
