# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_cu-2888
_database_code_depnum_ccdc_archive 'CCDC 2044593'
loop_
_audit_author_name
_audit_author_address
'Elisabeth Irran'
;Fakultat II Institutfur Chemie, Technische Universitat, Berlin
Germany
;
_audit_update_record             
;
2020-11-16 deposited with the CCDC.	2021-04-05 downloaded from the CCDC.
;

_audit_creation_method           'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H12 N2 O'
_chemical_formula_weight         248.28

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 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   Pbca

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'
'-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                   13.0833(3)
_cell_length_b                   7.64625(15)
_cell_length_c                   24.1850(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2419.43(8)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    3066
_cell_measurement_theta_min      4.9690
_cell_measurement_theta_max      73.5850

_exptl_crystal_description       rod
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.09
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.363
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1040
_exptl_absorpt_coefficient_mu    0.693
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8328
_exptl_absorpt_correction_T_max  0.9422
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150.00(10)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Atlas'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.5435
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8372
_diffrn_reflns_av_R_equivalents  0.0289
_diffrn_reflns_av_sigmaI/netI    0.0227
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         3.66
_diffrn_reflns_theta_max         67.50
_reflns_number_total             2185
_reflns_number_gt                1813
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_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)+(0.0530P)²+0.5498P] 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       0.00102(16)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2185
_refine_ls_number_parameters     177
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0478
_refine_ls_R_factor_gt           0.0377
_refine_ls_wR_factor_ref         0.1038
_refine_ls_wR_factor_gt          0.0943
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.001
_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
N1 N 0.89265(10) 0.06876(17) 0.70220(5) 0.0351(3) Uani 1 1 d . . .
N2 N 0.84716(10) 0.17743(16) 0.61331(5) 0.0344(3) Uani 1 1 d . . .
O1 O 0.95052(9) -0.02616(17) 0.79775(5) 0.0466(3) Uani 1 1 d . . .
C1 C 0.91333(12) 0.1354(2) 0.65235(6) 0.0379(4) Uani 1 1 d . . .
H1A H 0.9834 0.1546 0.6441 0.046 Uiso 1 1 calc R . .
C2 C 0.79335(11) 0.04405(18) 0.71530(6) 0.0277(3) Uani 1 1 d . . .
C3 C 0.71837(11) 0.08606(18) 0.67674(5) 0.0286(3) Uani 1 1 d . . .
H3A H 0.6481 0.0705 0.6854 0.034 Uiso 1 1 calc R . .
C4 C 0.74752(11) 0.15121(17) 0.62539(5) 0.0291(3) Uani 1 1 d . . .
C5 C 0.77183(11) -0.02566(17) 0.77109(6) 0.0276(3) Uani 1 1 d . . .
C6 C 0.85086(11) -0.05602(19) 0.80951(6) 0.0311(3) Uani 1 1 d . . .
C7 C 0.82758(12) -0.11852(19) 0.86227(6) 0.0347(4) Uani 1 1 d . . .
H7A H 0.8810 -0.1375 0.8882 0.042 Uiso 1 1 calc R . .
C8 C 0.72804(12) -0.15292(19) 0.87706(6) 0.0339(4) Uani 1 1 d . . .
H8A H 0.7132 -0.1961 0.9130 0.041 Uiso 1 1 calc R . .
C9 C 0.64940(12) -0.12489(19) 0.83976(6) 0.0355(4) Uani 1 1 d . . .
H9A H 0.5807 -0.1486 0.8500 0.043 Uiso 1 1 calc R . .
C10 C 0.67173(12) -0.06230(19) 0.78770(6) 0.0332(3) Uani 1 1 d . . .
H10A H 0.6174 -0.0435 0.7623 0.040 Uiso 1 1 calc R . .
C11 C 0.67275(12) 0.19584(18) 0.58165(5) 0.0302(3) Uani 1 1 d . . .
C12 C 0.57194(12) 0.1373(2) 0.58407(6) 0.0362(4) Uani 1 1 d . . .
H12A H 0.5502 0.0679 0.6145 0.043 Uiso 1 1 calc R . .
C13 C 0.50307(13) 0.1791(2) 0.54264(6) 0.0414(4) Uani 1 1 d . . .
H13A H 0.4348 0.1372 0.5446 0.050 Uiso 1 1 calc R . .
C14 C 0.53329(14) 0.2816(2) 0.49834(6) 0.0427(4) Uani 1 1 d . . .
H14A H 0.4859 0.3111 0.4701 0.051 Uiso 1 1 calc R . .
C15 C 0.63271(15) 0.3403(2) 0.49564(6) 0.0430(4) Uani 1 1 d . . .
H15A H 0.6535 0.4111 0.4654 0.052 Uiso 1 1 calc R . .
C16 C 0.70294(13) 0.2975(2) 0.53641(6) 0.0372(4) Uani 1 1 d . . .
H16A H 0.7716 0.3372 0.5336 0.045 Uiso 1 1 calc R . .
H1 H 0.951(2) 0.016(4) 0.7554(12) 0.111(10) Uiso 1 1 d . . .

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
N1 0.0286(7) 0.0452(7) 0.0315(7) 0.0029(6) 0.0011(5) -0.0038(6)
N2 0.0335(7) 0.0379(7) 0.0319(7) 0.0026(5) 0.0038(5) -0.0027(5)
O1 0.0292(6) 0.0738(8) 0.0369(6) 0.0054(6) -0.0034(5) 0.0017(6)
C1 0.0294(8) 0.0484(9) 0.0361(8) 0.0035(7) 0.0042(6) -0.0058(7)
C2 0.0286(7) 0.0278(7) 0.0265(7) -0.0028(5) 0.0003(6) -0.0023(6)
C3 0.0282(7) 0.0319(7) 0.0256(7) -0.0002(5) 0.0026(6) -0.0019(6)
C4 0.0342(7) 0.0255(7) 0.0275(7) -0.0024(5) 0.0032(6) 0.0009(6)
C5 0.0298(8) 0.0266(7) 0.0266(7) -0.0008(5) -0.0002(6) -0.0003(6)
C6 0.0281(7) 0.0348(7) 0.0304(8) -0.0018(6) -0.0006(6) 0.0025(6)
C7 0.0380(8) 0.0380(8) 0.0281(7) 0.0004(6) -0.0037(6) 0.0061(6)
C8 0.0440(9) 0.0310(7) 0.0266(7) 0.0031(6) 0.0037(6) 0.0035(7)
C9 0.0330(8) 0.0386(8) 0.0349(8) 0.0057(6) 0.0049(6) -0.0035(6)
C10 0.0302(8) 0.0377(8) 0.0316(8) 0.0051(6) -0.0030(6) -0.0020(6)
C11 0.0382(8) 0.0283(7) 0.0240(7) -0.0031(5) 0.0031(6) 0.0060(6)
C12 0.0366(8) 0.0439(9) 0.0282(8) 0.0035(6) 0.0009(6) 0.0061(7)
C13 0.0375(9) 0.0542(10) 0.0326(8) -0.0011(7) -0.0025(7) 0.0115(8)
C14 0.0553(11) 0.0457(10) 0.0269(8) -0.0018(7) -0.0043(7) 0.0199(8)
C15 0.0642(12) 0.0391(9) 0.0257(8) 0.0046(6) 0.0020(7) 0.0098(8)
C16 0.0491(10) 0.0345(8) 0.0280(8) 0.0014(6) 0.0051(7) 0.0021(7)

_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
N1 C1 1.3365(19) . ?
N1 C2 1.3506(19) . ?
N2 C1 1.321(2) . ?
N2 C4 1.3508(19) . ?
O1 C6 1.3539(19) . ?
C2 C3 1.3912(19) . ?
C2 C5 1.4776(19) . ?
C3 C4 1.3913(19) . ?
C4 C11 1.481(2) . ?
C5 C10 1.398(2) . ?
C5 C6 1.409(2) . ?
C6 C7 1.396(2) . ?
C7 C8 1.376(2) . ?
C8 C9 1.385(2) . ?
C9 C10 1.378(2) . ?
C11 C12 1.394(2) . ?
C11 C16 1.399(2) . ?
C12 C13 1.385(2) . ?
C13 C14 1.385(2) . ?
C14 C15 1.378(2) . ?
C15 C16 1.387(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
C1 N1 C2 117.37(13) . . ?
C1 N2 C4 116.22(12) . . ?
N2 C1 N1 127.22(14) . . ?
N1 C2 C3 119.25(13) . . ?
N1 C2 C5 116.61(13) . . ?
C3 C2 C5 124.14(13) . . ?
C2 C3 C4 119.20(14) . . ?
N2 C4 C3 120.71(13) . . ?
N2 C4 C11 116.67(12) . . ?
C3 C4 C11 122.62(13) . . ?
C10 C5 C6 117.69(13) . . ?
C10 C5 C2 120.86(13) . . ?
C6 C5 C2 121.45(13) . . ?
O1 C6 C7 117.38(13) . . ?
O1 C6 C5 122.69(13) . . ?
C7 C6 C5 119.92(14) . . ?
C8 C7 C6 120.64(14) . . ?
C7 C8 C9 120.27(13) . . ?
C10 C9 C8 119.42(15) . . ?
C9 C10 C5 122.05(14) . . ?
C12 C11 C16 118.58(14) . . ?
C12 C11 C4 121.40(13) . . ?
C16 C11 C4 120.02(14) . . ?
C13 C12 C11 120.73(15) . . ?
C12 C13 C14 120.30(16) . . ?
C15 C14 C13 119.38(15) . . ?
C14 C15 C16 121.00(15) . . ?
C15 C16 C11 120.00(16) . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        67.50
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.448
_refine_diff_density_min         -0.135
_refine_diff_density_rms         0.039
####################################################################### 
# 
# 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_cu-2886
_database_code_depnum_ccdc_archive 'CCDC 2044594'
loop_
_audit_author_name
_audit_author_address
'Elisabeth Irran'
;Fakultat II Institutfur Chemie, Technische Universitat, Berlin
Germany
;
_audit_update_record             
;
2020-11-16 deposited with the CCDC.	2021-04-05 downloaded from the CCDC.
;

_audit_creation_method           'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H14 N2 O2'
_chemical_formula_weight         278.30

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

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/c

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                   11.3261(3)
_cell_length_b                   15.5298(4)
_cell_length_c                   8.0963(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 105.260(3)
_cell_angle_gamma                90.00
_cell_volume                     1373.87(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    4237
_cell_measurement_theta_min      4.0190
_cell_measurement_theta_max      73.4760

_exptl_crystal_description       rhomb
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.06
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.345
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             584
_exptl_absorpt_coefficient_mu    0.725
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8793
_exptl_absorpt_correction_T_max  0.9571
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150.00(10)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Atlas'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.5435
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8343
_diffrn_reflns_av_R_equivalents  0.0195
_diffrn_reflns_av_sigmaI/netI    0.0160
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         4.05
_diffrn_reflns_theta_max         67.49
_reflns_number_total             2480
_reflns_number_gt                2197
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_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)+(0.0522P)²+0.3119P] 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         2480
_refine_ls_number_parameters     195
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0398
_refine_ls_R_factor_gt           0.0347
_refine_ls_wR_factor_ref         0.0942
_refine_ls_wR_factor_gt          0.0887
_refine_ls_goodness_of_fit_ref   1.034
_refine_ls_restrained_S_all      1.034
_refine_ls_shift/su_max          0.001
_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
N1 N 0.90458(9) 0.51767(6) 0.18496(12) 0.0243(2) Uani 1 1 d . . .
N2 N 0.72351(9) 0.60024(7) 0.08042(12) 0.0261(2) Uani 1 1 d . . .
O1 O 1.10458(8) 0.43654(6) 0.29488(11) 0.0299(2) Uani 1 1 d . . .
H1 H 1.0436(18) 0.4766(13) 0.235(2) 0.062(5) Uiso 1 1 d . . .
O2 O 0.49478(7) 0.45399(6) 0.30812(11) 0.0315(2) Uani 1 1 d . . .
C1 C 0.83817(11) 0.57968(8) 0.09037(14) 0.0257(3) Uani 1 1 d . . .
H1A H 0.8780 0.6129 0.0223 0.031 Uiso 1 1 calc R . .
C2 C 0.84980(10) 0.47125(7) 0.28483(14) 0.0216(2) Uani 1 1 d . . .
C3 C 0.72838(10) 0.48774(8) 0.28137(15) 0.0239(3) Uani 1 1 d . . .
H3A H 0.6888 0.4549 0.3501 0.029 Uiso 1 1 calc R . .
C4 C 0.66575(10) 0.55281(7) 0.17632(14) 0.0232(3) Uani 1 1 d . . .
C5 C 0.92510(10) 0.40467(7) 0.39469(14) 0.0216(3) Uani 1 1 d . . .
C6 C 1.04858(10) 0.39107(7) 0.39497(14) 0.0229(3) Uani 1 1 d . . .
C7 C 1.11759(11) 0.32820(8) 0.50072(14) 0.0261(3) Uani 1 1 d . . .
H7A H 1.2005 0.3194 0.5004 0.031 Uiso 1 1 calc R . .
C8 C 1.06699(11) 0.27873(8) 0.60552(15) 0.0272(3) Uani 1 1 d . . .
H8A H 1.1149 0.2359 0.6764 0.033 Uiso 1 1 calc R . .
C9 C 0.94563(11) 0.29141(8) 0.60782(15) 0.0287(3) Uani 1 1 d . . .
H9A H 0.9106 0.2575 0.6803 0.034 Uiso 1 1 calc R . .
C10 C 0.87686(11) 0.35344(8) 0.50436(15) 0.0260(3) Uani 1 1 d . . .
H10A H 0.7943 0.3619 0.5071 0.031 Uiso 1 1 calc R . .
C11 C 0.53666(10) 0.57787(8) 0.16232(15) 0.0252(3) Uani 1 1 d . . .
C12 C 0.45393(10) 0.52963(8) 0.22875(14) 0.0251(3) Uani 1 1 d . . .
C13 C 0.33524(11) 0.55929(9) 0.21169(16) 0.0297(3) Uani 1 1 d . . .
H13A H 0.2806 0.5269 0.2584 0.036 Uiso 1 1 calc R . .
C14 C 0.29655(12) 0.63582(9) 0.12692(19) 0.0385(3) Uani 1 1 d . . .
H14A H 0.2156 0.6558 0.1163 0.046 Uiso 1 1 calc R . .
C15 C 0.37514(13) 0.68325(9) 0.0576(2) 0.0445(4) Uani 1 1 d . . .
H15A H 0.3481 0.7352 -0.0023 0.053 Uiso 1 1 calc R . .
C16 C 0.49333(12) 0.65435(9) 0.07616(18) 0.0360(3) Uani 1 1 d . . .
H16A H 0.5469 0.6875 0.0289 0.043 Uiso 1 1 calc R . .
C17 C 0.40917(11) 0.39902(9) 0.35893(17) 0.0326(3) Uani 1 1 d . . .
H17A H 0.4512 0.3470 0.4129 0.049 Uiso 1 1 calc R . .
H17B H 0.3438 0.3829 0.2580 0.049 Uiso 1 1 calc R . .
H17C H 0.3739 0.4295 0.4407 0.049 Uiso 1 1 calc R . .

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
N1 0.0226(5) 0.0269(5) 0.0242(5) -0.0003(4) 0.0079(4) -0.0028(4)
N2 0.0250(5) 0.0286(6) 0.0246(5) 0.0005(4) 0.0061(4) -0.0019(4)
O1 0.0224(4) 0.0371(5) 0.0334(5) 0.0068(4) 0.0132(4) 0.0020(4)
O2 0.0199(4) 0.0347(5) 0.0407(5) 0.0112(4) 0.0095(4) 0.0008(3)
C1 0.0243(6) 0.0294(6) 0.0240(6) 0.0014(5) 0.0073(5) -0.0032(5)
C2 0.0207(5) 0.0228(6) 0.0216(5) -0.0044(4) 0.0062(4) -0.0040(4)
C3 0.0213(6) 0.0253(6) 0.0260(6) 0.0000(4) 0.0079(4) -0.0018(4)
C4 0.0223(6) 0.0241(6) 0.0230(5) -0.0047(4) 0.0053(4) -0.0033(4)
C5 0.0202(5) 0.0218(6) 0.0229(5) -0.0041(4) 0.0056(4) -0.0020(4)
C6 0.0220(6) 0.0256(6) 0.0224(5) -0.0050(4) 0.0082(4) -0.0033(4)
C7 0.0216(6) 0.0295(7) 0.0268(6) -0.0044(5) 0.0057(5) 0.0023(5)
C8 0.0296(6) 0.0246(6) 0.0252(6) -0.0019(5) 0.0035(5) 0.0033(5)
C9 0.0304(6) 0.0263(6) 0.0306(6) 0.0023(5) 0.0103(5) -0.0027(5)
C10 0.0215(6) 0.0271(6) 0.0303(6) -0.0003(5) 0.0086(5) -0.0029(5)
C11 0.0217(6) 0.0262(6) 0.0267(6) -0.0031(5) 0.0049(5) 0.0000(5)
C12 0.0213(6) 0.0288(6) 0.0237(5) -0.0026(5) 0.0032(4) 0.0007(5)
C13 0.0218(6) 0.0343(7) 0.0332(6) -0.0040(5) 0.0074(5) -0.0002(5)
C14 0.0250(6) 0.0374(8) 0.0534(8) -0.0017(6) 0.0108(6) 0.0082(6)
C15 0.0350(7) 0.0324(7) 0.0667(10) 0.0099(7) 0.0144(7) 0.0120(6)
C16 0.0307(7) 0.0291(7) 0.0495(8) 0.0050(6) 0.0131(6) 0.0021(5)
C17 0.0233(6) 0.0389(8) 0.0364(7) 0.0089(5) 0.0091(5) -0.0035(5)

_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
N1 C1 1.3328(16) . ?
N1 C2 1.3500(14) . ?
N2 C1 1.3190(15) . ?
N2 C4 1.3568(15) . ?
O1 C6 1.3520(14) . ?
O2 C12 1.3604(15) . ?
O2 C17 1.4310(14) . ?
C2 C3 1.3918(16) . ?
C2 C5 1.4793(16) . ?
C3 C4 1.3893(17) . ?
C4 C11 1.4881(16) . ?
C5 C10 1.4055(16) . ?
C5 C6 1.4139(16) . ?
C6 C7 1.3947(17) . ?
C7 C8 1.3763(17) . ?
C8 C9 1.3935(17) . ?
C9 C10 1.3758(17) . ?
C11 C16 1.3992(18) . ?
C11 C12 1.4120(17) . ?
C12 C13 1.3931(17) . ?
C13 C14 1.3846(19) . ?
C14 C15 1.383(2) . ?
C15 C16 1.3821(19) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C2 116.82(10) . . ?
C1 N2 C4 116.67(10) . . ?
C12 O2 C17 118.61(9) . . ?
N2 C1 N1 127.43(11) . . ?
N1 C2 C3 119.81(11) . . ?
N1 C2 C5 116.76(10) . . ?
C3 C2 C5 123.43(10) . . ?
C4 C3 C2 119.26(11) . . ?
N2 C4 C3 119.99(11) . . ?
N2 C4 C11 115.24(10) . . ?
C3 C4 C11 124.75(10) . . ?
C10 C5 C6 117.60(11) . . ?
C10 C5 C2 121.14(10) . . ?
C6 C5 C2 121.26(10) . . ?
O1 C6 C7 117.27(10) . . ?
O1 C6 C5 122.74(10) . . ?
C7 C6 C5 119.99(10) . . ?
C8 C7 C6 120.81(11) . . ?
C7 C8 C9 120.11(11) . . ?
C10 C9 C8 119.55(11) . . ?
C9 C10 C5 121.94(11) . . ?
C16 C11 C12 117.34(11) . . ?
C16 C11 C4 117.95(11) . . ?
C12 C11 C4 124.71(11) . . ?
O2 C12 C13 122.12(11) . . ?
O2 C12 C11 117.44(10) . . ?
C13 C12 C11 120.44(11) . . ?
C14 C13 C12 120.28(12) . . ?
C15 C14 C13 120.32(12) . . ?
C16 C15 C14 119.42(13) . . ?
C15 C16 C11 122.18(12) . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        67.49
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.114
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.046
####################################################################### 
# 
# 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_cu-2903
_database_code_depnum_ccdc_archive 'CCDC 2044597'
loop_
_audit_author_name
_audit_author_address
'Elisabeth Irran'
;Fakultat II Institutfur Chemie, Technische Universitat, Berlin
Germany
;
_audit_update_record             
;
2020-11-16 deposited with the CCDC.	2021-04-05 downloaded from the CCDC.
;

_audit_creation_method           'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H11 N O3'
_chemical_formula_weight         253.25

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   P21/c

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                   14.5352(4)
_cell_length_b                   11.5897(3)
_cell_length_c                   14.2576(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.137(3)
_cell_angle_gamma                90.00
_cell_volume                     2348.13(14)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2527
_cell_measurement_theta_min      4.8980
_cell_measurement_theta_max      73.3020

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.433
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1056
_exptl_absorpt_coefficient_mu    0.832
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7353
_exptl_absorpt_correction_T_max  0.9651
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150.00(10)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Atlas'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.5435
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            8922
_diffrn_reflns_av_R_equivalents  0.0383
_diffrn_reflns_av_sigmaI/netI    0.0473
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.11
_diffrn_reflns_theta_max         67.50
_reflns_number_total             4222
_reflns_number_gt                2892
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_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)+(0.0704P)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_number_reflns         4222
_refine_ls_number_parameters     355
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0753
_refine_ls_R_factor_gt           0.0476
_refine_ls_wR_factor_ref         0.1347
_refine_ls_wR_factor_gt          0.1139
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_restrained_S_all      1.003
_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
N1 N 0.95459(11) 0.65087(15) 0.18106(15) 0.0399(5) Uani 1 1 d . . .
N2 N 0.80007(11) 0.64649(16) 0.41270(16) 0.0439(5) Uani 1 1 d . . .
O1 O 0.85634(9) 0.66219(12) 0.16745(12) 0.0400(4) Uani 1 1 d . . .
O2 O 1.12418(10) 0.57182(13) 0.19015(13) 0.0483(5) Uani 1 1 d . . .
H2 H 1.0625(18) 0.573(2) 0.1883(18) 0.058 Uiso 1 1 d . . .
O3 O 0.45359(9) 0.89912(15) 0.09918(14) 0.0516(5) Uani 1 1 d . . .
H3 H 0.4458(17) 0.980(2) 0.1046(19) 0.062 Uiso 1 1 d . . .
O4 O 0.89795(9) 0.63121(13) 0.42521(12) 0.0436(4) Uani 1 1 d . . .
O5 O 0.61890(11) 0.61352(14) 0.37809(15) 0.0556(5) Uani 1 1 d . . .
H5 H 0.6780(19) 0.591(2) 0.389(2) 0.067 Uiso 1 1 d . . .
O6 O 1.33177(10) 0.76573(16) 0.49081(13) 0.0529(5) Uani 1 1 d . . .
H6 H 1.3629(18) 0.704(2) 0.522(2) 0.064 Uiso 1 1 d . . .
C1 C 0.83526(13) 0.77610(17) 0.16414(15) 0.0316(5) Uani 1 1 d . . .
C2 C 0.91540(13) 0.83830(18) 0.17463(16) 0.0338(5) Uani 1 1 d . . .
H2A H 0.9212 0.9200 0.1750 0.041 Uiso 1 1 calc R . .
C3 C 0.98866(13) 0.75631(17) 0.18490(15) 0.0295(4) Uani 1 1 d . . .
C4 C 0.73572(13) 0.80711(18) 0.15045(16) 0.0329(5) Uani 1 1 d . . .
C5 C 0.71051(13) 0.92246(19) 0.14882(18) 0.0429(6) Uani 1 1 d . . .
H5A H 0.7581 0.9800 0.1589 0.051 Uiso 1 1 calc R . .
C6 C 0.61712(14) 0.9551(2) 0.13269(19) 0.0469(6) Uani 1 1 d . . .
H6B H 0.6005 1.0345 0.1315 0.056 Uiso 1 1 calc R . .
C7 C 0.54780(13) 0.87094(19) 0.11828(17) 0.0392(5) Uani 1 1 d . . .
C8 C 0.57163(14) 0.75670(19) 0.12169(18) 0.0436(6) Uani 1 1 d . . .
H8A H 0.5238 0.6994 0.1136 0.052 Uiso 1 1 calc R . .
C9 C 0.66549(14) 0.7242(2) 0.13701(17) 0.0403(5) Uani 1 1 d . . .
H9A H 0.6817 0.6447 0.1383 0.048 Uiso 1 1 calc R . .
C10 C 1.09044(13) 0.77547(18) 0.19936(15) 0.0299(5) Uani 1 1 d . . .
C11 C 1.12732(13) 0.88682(19) 0.21193(16) 0.0374(5) Uani 1 1 d . . .
H11A H 1.0857 0.9502 0.2111 0.045 Uiso 1 1 calc R . .
C12 C 1.22277(14) 0.9072(2) 0.22548(17) 0.0411(6) Uani 1 1 d . . .
H12A H 1.2465 0.9837 0.2341 0.049 Uiso 1 1 calc R . .
C13 C 1.28361(13) 0.8151(2) 0.22638(16) 0.0402(5) Uani 1 1 d . . .
H13A H 1.3494 0.8286 0.2354 0.048 Uiso 1 1 calc R . .
C14 C 1.24940(14) 0.70427(19) 0.21428(17) 0.0411(6) Uani 1 1 d . . .
H14A H 1.2916 0.6416 0.2147 0.049 Uiso 1 1 calc R . .
C15 C 1.15345(13) 0.68369(18) 0.20152(16) 0.0345(5) Uani 1 1 d . . .
C16 C 0.93845(13) 0.73699(17) 0.42902(15) 0.0313(5) Uani 1 1 d . . .
C17 C 0.87117(13) 0.81887(19) 0.41938(16) 0.0349(5) Uani 1 1 d . . .
H17A H 0.8796 0.9002 0.4196 0.042 Uiso 1 1 calc R . .
C18 C 0.78518(13) 0.75774(18) 0.40886(16) 0.0325(5) Uani 1 1 d . . .
C19 C 1.04045(13) 0.74073(18) 0.44307(15) 0.0311(5) Uani 1 1 d . . .
C20 C 1.08552(13) 0.84545(19) 0.43516(16) 0.0376(5) Uani 1 1 d . . .
H20A H 1.0491 0.9135 0.4194 0.045 Uiso 1 1 calc R . .
C21 C 1.18215(14) 0.8515(2) 0.44986(17) 0.0427(6) Uani 1 1 d . . .
H21A H 1.2119 0.9230 0.4428 0.051 Uiso 1 1 calc R . .
C22 C 1.23590(13) 0.7533(2) 0.47490(16) 0.0389(5) Uani 1 1 d . . .
C23 C 1.19264(14) 0.64867(19) 0.48221(17) 0.0400(5) Uani 1 1 d . . .
H23A H 1.2294 0.5809 0.4980 0.048 Uiso 1 1 calc R . .
C24 C 1.09558(13) 0.64300(19) 0.46641(16) 0.0368(5) Uani 1 1 d . . .
H24A H 1.0661 0.5708 0.4716 0.044 Uiso 1 1 calc R . .
C25 C 0.68935(13) 0.80300(19) 0.39811(16) 0.0357(5) Uani 1 1 d . . .
C26 C 0.67491(15) 0.9199(2) 0.4034(2) 0.0523(7) Uani 1 1 d . . .
H26A H 0.7273 0.9706 0.4107 0.063 Uiso 1 1 calc R . .
C27 C 0.58610(16) 0.9657(2) 0.3985(2) 0.0675(9) Uani 1 1 d . . .
H27A H 0.5779 1.0466 0.4040 0.081 Uiso 1 1 calc R . .
C28 C 0.50957(15) 0.8924(2) 0.3855(2) 0.0573(7) Uani 1 1 d . . .
H28A H 0.4483 0.9231 0.3816 0.069 Uiso 1 1 calc R . .
C29 C 0.52143(14) 0.7762(2) 0.37813(18) 0.0478(6) Uani 1 1 d . . .
H29A H 0.4683 0.7265 0.3685 0.057 Uiso 1 1 calc R . .
C30 C 0.61076(14) 0.7304(2) 0.38469(17) 0.0389(5) Uani 1 1 d . . .

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
N1 0.0248(8) 0.0364(10) 0.0590(13) 0.0020(9) 0.0096(8) 0.0010(7)
N2 0.0233(8) 0.0420(11) 0.0682(14) -0.0042(10) 0.0135(8) -0.0009(7)
O1 0.0244(7) 0.0341(8) 0.0616(11) 0.0025(7) 0.0095(6) -0.0007(6)
O2 0.0324(8) 0.0315(8) 0.0810(13) 0.0011(8) 0.0118(8) 0.0020(7)
O3 0.0227(7) 0.0489(10) 0.0833(14) -0.0040(10) 0.0111(7) 0.0013(7)
O4 0.0261(7) 0.0360(8) 0.0707(12) -0.0026(8) 0.0143(7) -0.0019(6)
O5 0.0282(8) 0.0432(10) 0.0959(15) 0.0021(10) 0.0141(9) -0.0045(7)
O6 0.0241(7) 0.0715(12) 0.0628(12) 0.0093(10) 0.0082(7) -0.0028(7)
C1 0.0286(10) 0.0317(11) 0.0354(12) -0.0007(9) 0.0088(9) 0.0007(8)
C2 0.0281(9) 0.0319(11) 0.0426(13) -0.0014(10) 0.0100(9) 0.0000(8)
C3 0.0287(9) 0.0314(11) 0.0297(11) 0.0012(9) 0.0092(8) 0.0008(8)
C4 0.0254(9) 0.0386(12) 0.0359(12) 0.0008(10) 0.0092(8) -0.0013(9)
C5 0.0263(10) 0.0365(12) 0.0669(17) -0.0041(12) 0.0122(10) -0.0031(9)
C6 0.0291(11) 0.0366(12) 0.0752(18) -0.0029(12) 0.0114(11) 0.0005(9)
C7 0.0229(9) 0.0439(13) 0.0516(15) -0.0010(11) 0.0093(9) 0.0014(9)
C8 0.0282(10) 0.0401(13) 0.0634(17) -0.0013(12) 0.0121(10) -0.0068(9)
C9 0.0320(10) 0.0378(12) 0.0526(15) 0.0007(11) 0.0121(10) -0.0016(9)
C10 0.0269(9) 0.0321(11) 0.0314(12) 0.0017(9) 0.0073(8) 0.0016(8)
C11 0.0329(10) 0.0359(12) 0.0445(14) -0.0011(10) 0.0104(9) -0.0001(9)
C12 0.0352(11) 0.0409(13) 0.0478(14) -0.0013(11) 0.0102(10) -0.0088(10)
C13 0.0256(10) 0.0529(14) 0.0424(14) 0.0036(11) 0.0074(9) -0.0035(10)
C14 0.0295(10) 0.0441(13) 0.0510(15) 0.0052(11) 0.0118(10) 0.0058(9)
C15 0.0301(10) 0.0339(11) 0.0396(13) 0.0017(10) 0.0074(9) 0.0011(9)
C16 0.0287(10) 0.0322(11) 0.0343(12) -0.0002(9) 0.0094(8) -0.0036(8)
C17 0.0260(9) 0.0335(11) 0.0457(14) 0.0031(10) 0.0088(9) -0.0026(8)
C18 0.0298(10) 0.0347(12) 0.0344(12) -0.0028(9) 0.0100(9) -0.0020(8)
C19 0.0265(9) 0.0379(12) 0.0299(11) 0.0018(9) 0.0087(8) 0.0003(8)
C20 0.0303(10) 0.0405(12) 0.0410(13) 0.0075(10) 0.0056(9) -0.0017(9)
C21 0.0329(11) 0.0471(14) 0.0475(15) 0.0070(11) 0.0069(10) -0.0079(10)
C22 0.0228(9) 0.0563(15) 0.0380(13) 0.0007(11) 0.0075(9) -0.0036(9)
C23 0.0300(10) 0.0442(13) 0.0468(14) 0.0025(11) 0.0105(9) 0.0082(9)
C24 0.0312(10) 0.0362(12) 0.0443(13) 0.0004(10) 0.0111(9) -0.0018(9)
C25 0.0255(9) 0.0430(13) 0.0397(13) -0.0030(10) 0.0092(9) -0.0005(9)
C26 0.0322(11) 0.0427(14) 0.080(2) -0.0077(13) 0.0081(12) 0.0013(10)
C27 0.0381(13) 0.0511(16) 0.111(3) -0.0161(17) 0.0105(14) 0.0099(12)
C28 0.0278(11) 0.0648(17) 0.079(2) -0.0114(15) 0.0096(12) 0.0075(11)
C29 0.0279(10) 0.0603(16) 0.0563(17) -0.0029(13) 0.0115(10) -0.0035(10)
C30 0.0301(10) 0.0434(13) 0.0445(14) -0.0013(11) 0.0108(9) -0.0021(9)

_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
N1 C3 1.315(3) . ?
N1 O1 1.406(2) . ?
N2 C18 1.307(3) . ?
N2 O4 1.407(2) . ?
O1 C1 1.354(2) . ?
O2 C15 1.364(3) . ?
O3 C7 1.378(2) . ?
O4 C16 1.356(2) . ?
O5 C30 1.365(3) . ?
O6 C22 1.372(2) . ?
C1 C2 1.351(3) . ?
C1 C4 1.463(3) . ?
C2 C3 1.412(3) . ?
C3 C10 1.467(2) . ?
C4 C5 1.385(3) . ?
C4 C9 1.386(3) . ?
C5 C6 1.381(3) . ?
C6 C7 1.386(3) . ?
C7 C8 1.367(3) . ?
C8 C9 1.388(3) . ?
C10 C11 1.394(3) . ?
C10 C15 1.400(3) . ?
C11 C12 1.380(3) . ?
C12 C13 1.384(3) . ?
C13 C14 1.375(3) . ?
C14 C15 1.389(3) . ?
C16 C17 1.349(3) . ?
C16 C19 1.454(3) . ?
C17 C18 1.417(3) . ?
C18 C25 1.466(3) . ?
C19 C24 1.387(3) . ?
C19 C20 1.395(3) . ?
C20 C21 1.378(3) . ?
C21 C22 1.384(3) . ?
C22 C23 1.380(3) . ?
C23 C24 1.383(3) . ?
C25 C26 1.376(3) . ?
C25 C30 1.399(3) . ?
C26 C27 1.384(3) . ?
C27 C28 1.380(4) . ?
C28 C29 1.365(4) . ?
C29 C30 1.388(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
C3 N1 O1 106.35(15) . . ?
C18 N2 O4 106.47(16) . . ?
C1 O1 N1 108.16(14) . . ?
C16 O4 N2 108.07(15) . . ?
C2 C1 O1 109.44(16) . . ?
C2 C1 C4 133.54(19) . . ?
O1 C1 C4 117.02(17) . . ?
C1 C2 C3 105.45(18) . . ?
N1 C3 C2 110.60(16) . . ?
N1 C3 C10 120.40(17) . . ?
C2 C3 C10 128.99(18) . . ?
C5 C4 C9 118.86(18) . . ?
C5 C4 C1 119.33(18) . . ?
C9 C4 C1 121.79(19) . . ?
C6 C5 C4 121.0(2) . . ?
C5 C6 C7 119.4(2) . . ?
C8 C7 O3 118.07(19) . . ?
C8 C7 C6 120.36(19) . . ?
O3 C7 C6 121.6(2) . . ?
C7 C8 C9 120.15(19) . . ?
C4 C9 C8 120.3(2) . . ?
C11 C10 C15 117.93(17) . . ?
C11 C10 C3 120.47(18) . . ?
C15 C10 C3 121.60(18) . . ?
C12 C11 C10 121.6(2) . . ?
C11 C12 C13 119.4(2) . . ?
C14 C13 C12 120.36(18) . . ?
C13 C14 C15 120.2(2) . . ?
O2 C15 C14 117.30(18) . . ?
O2 C15 C10 122.25(17) . . ?
C14 C15 C10 120.45(19) . . ?
C17 C16 O4 109.42(16) . . ?
C17 C16 C19 133.58(19) . . ?
O4 C16 C19 116.99(17) . . ?
C16 C17 C18 105.28(19) . . ?
N2 C18 C17 110.75(17) . . ?
N2 C18 C25 120.19(18) . . ?
C17 C18 C25 129.03(19) . . ?
C24 C19 C20 118.19(18) . . ?
C24 C19 C16 121.97(18) . . ?
C20 C19 C16 119.82(18) . . ?
C21 C20 C19 120.8(2) . . ?
C20 C21 C22 120.0(2) . . ?
O6 C22 C23 122.9(2) . . ?
O6 C22 C21 117.09(19) . . ?
C23 C22 C21 120.03(18) . . ?
C22 C23 C24 119.66(19) . . ?
C23 C24 C19 121.2(2) . . ?
C26 C25 C30 118.03(19) . . ?
C26 C25 C18 119.95(19) . . ?
C30 C25 C18 122.0(2) . . ?
C25 C26 C27 121.8(2) . . ?
C28 C27 C26 119.2(3) . . ?
C29 C28 C27 120.4(2) . . ?
C28 C29 C30 120.3(2) . . ?
O5 C30 C29 117.94(19) . . ?
O5 C30 C25 121.73(18) . . ?
C29 C30 C25 120.3(2) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        67.50
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.204
_refine_diff_density_min         -0.260
_refine_diff_density_rms         0.047
####################################################################### 
# 
# 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_cu-2896
_database_code_depnum_ccdc_archive 'CCDC 2044595'
loop_
_audit_author_name
_audit_author_address
'Elisabeth Irran'
;Fakultat II Institutfur Chemie, Technische Universitat, Berlin
Germany
;
_audit_update_record             
;
2020-11-16 deposited with the CCDC.	2021-04-05 downloaded from the CCDC.
;

_audit_creation_method           'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H13 N O3'
_chemical_formula_weight         267.27

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   P21/n

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

_cell_length_a                   5.55659(18)
_cell_length_b                   10.0324(3)
_cell_length_c                   22.5154(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.490(3)
_cell_angle_gamma                90.00
_cell_volume                     1253.96(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    1912
_cell_measurement_theta_min      3.9020
_cell_measurement_theta_max      73.4660

_exptl_crystal_description       rod
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.416
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             560
_exptl_absorpt_coefficient_mu    0.808
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7908
_exptl_absorpt_correction_T_max  0.9638
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150.00(10)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Atlas'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.5435
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4420
_diffrn_reflns_av_R_equivalents  0.0234
_diffrn_reflns_av_sigmaI/netI    0.0309
_diffrn_reflns_limit_h_min       -2
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         3.93
_diffrn_reflns_theta_max         67.49
_reflns_number_total             2255
_reflns_number_gt                1837
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_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)+(0.0565P)²+0.1377P] 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       0.0024(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2255
_refine_ls_number_parameters     186
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0475
_refine_ls_R_factor_gt           0.0366
_refine_ls_wR_factor_ref         0.1031
_refine_ls_wR_factor_gt          0.0949
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_refine_ls_shift/su_max          0.001
_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
O1 O 0.44305(18) 0.90133(11) 0.56685(4) 0.0319(3) Uani 1 1 d . . .
O2 O 1.01716(19) 1.01893(12) 0.66390(5) 0.0343(3) Uani 1 1 d . . .
H2 H 0.901(3) 1.0118(19) 0.6353(8) 0.041 Uiso 1 1 d . . .
O3 O 0.00559(18) 0.58642(11) 0.61213(4) 0.0327(3) Uani 1 1 d . . .
N1 N 0.6292(2) 0.92638(13) 0.60902(5) 0.0316(3) Uani 1 1 d . . .
C1 C 0.6087(3) 0.83707(15) 0.65148(6) 0.0267(3) Uani 1 1 d . . .
C2 C 0.4085(2) 0.75222(15) 0.63890(6) 0.0266(3) Uani 1 1 d . . .
H2A H 0.3536 0.6808 0.6625 0.032 Uiso 1 1 calc R . .
C3 C 0.3127(3) 0.79533(15) 0.58590(6) 0.0271(3) Uani 1 1 d . . .
C4 C 0.7858(3) 0.83466(15) 0.70210(6) 0.0265(3) Uani 1 1 d . . .
C5 C 0.7680(3) 0.73921(16) 0.74680(7) 0.0314(4) Uani 1 1 d . . .
H5A H 0.6363 0.6788 0.7452 0.038 Uiso 1 1 calc R . .
C6 C 0.9377(3) 0.73068(17) 0.79327(7) 0.0352(4) Uani 1 1 d . . .
H6A H 0.9237 0.6644 0.8231 0.042 Uiso 1 1 calc R . .
C7 C 1.1290(3) 0.81976(17) 0.79613(7) 0.0344(4) Uani 1 1 d . . .
H7A H 1.2465 0.8141 0.8280 0.041 Uiso 1 1 calc R . .
C8 C 1.1497(3) 0.91633(17) 0.75308(7) 0.0323(4) Uani 1 1 d . . .
H8A H 1.2796 0.9780 0.7558 0.039 Uiso 1 1 calc R . .
C9 C 0.9807(3) 0.92383(16) 0.70555(6) 0.0278(3) Uani 1 1 d . . .
C10 C 0.1106(3) 0.75697(15) 0.54575(6) 0.0269(3) Uani 1 1 d . . .
C11 C -0.0431(3) 0.65108(15) 0.55968(6) 0.0279(3) Uani 1 1 d . . .
C12 C -0.2356(3) 0.61783(17) 0.52078(7) 0.0329(4) Uani 1 1 d . . .
H12A H -0.3371 0.5449 0.5296 0.039 Uiso 1 1 calc R . .
C13 C -0.2792(3) 0.69097(18) 0.46933(7) 0.0361(4) Uani 1 1 d . . .
H13A H -0.4127 0.6688 0.4434 0.043 Uiso 1 1 calc R . .
C14 C -0.1311(3) 0.79573(18) 0.45522(7) 0.0363(4) Uani 1 1 d . . .
H14A H -0.1626 0.8458 0.4199 0.044 Uiso 1 1 calc R . .
C15 C 0.0639(3) 0.82723(17) 0.49299(6) 0.0315(4) Uani 1 1 d . . .
H15A H 0.1679 0.8980 0.4828 0.038 Uiso 1 1 calc R . .
C16 C -0.1577(3) 0.48434(17) 0.62897(7) 0.0339(4) Uani 1 1 d . . .
H16A H -0.1153 0.4549 0.6696 0.051 Uiso 1 1 calc R . .
H16B H -0.1474 0.4087 0.6017 0.051 Uiso 1 1 calc R . .
H16C H -0.3224 0.5195 0.6272 0.051 Uiso 1 1 calc R . .

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
O1 0.0346(6) 0.0323(6) 0.0283(5) 0.0022(5) -0.0023(4) -0.0056(5)
O2 0.0338(6) 0.0352(6) 0.0337(6) 0.0052(5) -0.0001(5) -0.0075(5)
O3 0.0343(6) 0.0333(6) 0.0302(5) 0.0056(5) -0.0029(4) -0.0056(5)
N1 0.0328(7) 0.0333(7) 0.0283(6) 0.0011(6) -0.0029(5) -0.0047(6)
C1 0.0295(7) 0.0248(8) 0.0260(7) -0.0022(6) 0.0043(6) 0.0021(6)
C2 0.0275(7) 0.0266(8) 0.0259(7) -0.0009(6) 0.0039(5) 0.0003(6)
C3 0.0280(7) 0.0257(8) 0.0281(7) -0.0031(6) 0.0063(6) 0.0019(6)
C4 0.0268(7) 0.0262(8) 0.0265(7) -0.0033(6) 0.0033(5) 0.0018(6)
C5 0.0326(8) 0.0301(8) 0.0316(8) 0.0001(7) 0.0023(6) -0.0028(7)
C6 0.0377(9) 0.0365(9) 0.0314(8) 0.0053(7) 0.0006(6) -0.0004(7)
C7 0.0312(8) 0.0410(10) 0.0306(8) -0.0013(7) -0.0024(6) 0.0014(7)
C8 0.0267(7) 0.0356(9) 0.0345(8) -0.0034(7) 0.0018(6) -0.0030(6)
C9 0.0290(7) 0.0273(8) 0.0276(7) -0.0019(6) 0.0072(6) 0.0010(6)
C10 0.0286(7) 0.0274(8) 0.0247(7) -0.0036(6) 0.0032(6) 0.0035(6)
C11 0.0308(8) 0.0279(8) 0.0251(7) -0.0008(6) 0.0019(6) 0.0035(6)
C12 0.0315(8) 0.0358(9) 0.0314(8) 0.0000(7) 0.0007(6) -0.0044(7)
C13 0.0333(8) 0.0455(10) 0.0291(8) -0.0001(7) -0.0038(6) -0.0026(7)
C14 0.0395(9) 0.0433(10) 0.0261(7) 0.0044(7) 0.0001(6) 0.0014(7)
C15 0.0340(8) 0.0330(9) 0.0278(7) 0.0006(7) 0.0037(6) 0.0006(7)
C16 0.0317(8) 0.0322(9) 0.0377(8) 0.0065(7) -0.0010(6) -0.0034(7)

_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 C3 1.3661(19) . ?
O1 N1 1.3962(15) . ?
O2 C9 1.3589(19) . ?
O3 C11 1.3640(18) . ?
O3 C16 1.4304(18) . ?
N1 C1 1.3188(19) . ?
C1 C2 1.420(2) . ?
C1 C4 1.473(2) . ?
C2 C3 1.356(2) . ?
C3 C10 1.462(2) . ?
C4 C5 1.396(2) . ?
C4 C9 1.404(2) . ?
C5 C6 1.380(2) . ?
C6 C7 1.388(2) . ?
C7 C8 1.379(2) . ?
C8 C9 1.395(2) . ?
C10 C15 1.396(2) . ?
C10 C11 1.407(2) . ?
C11 C12 1.394(2) . ?
C12 C13 1.384(2) . ?
C13 C14 1.381(2) . ?
C14 C15 1.384(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
C3 O1 N1 108.29(11) . . ?
C11 O3 C16 117.76(11) . . ?
C1 N1 O1 106.61(12) . . ?
N1 C1 C2 110.76(12) . . ?
N1 C1 C4 119.74(14) . . ?
C2 C1 C4 129.48(14) . . ?
C3 C2 C1 104.97(13) . . ?
C2 C3 O1 109.36(12) . . ?
C2 C3 C10 136.18(15) . . ?
O1 C3 C10 114.46(12) . . ?
C5 C4 C9 118.40(13) . . ?
C5 C4 C1 120.22(14) . . ?
C9 C4 C1 121.33(14) . . ?
C6 C5 C4 121.45(15) . . ?
C5 C6 C7 119.45(15) . . ?
C8 C7 C6 120.46(14) . . ?
C7 C8 C9 120.21(15) . . ?
O2 C9 C8 116.85(14) . . ?
O2 C9 C4 123.15(13) . . ?
C8 C9 C4 120.00(14) . . ?
C15 C10 C11 118.62(13) . . ?
C15 C10 C3 120.17(14) . . ?
C11 C10 C3 121.21(13) . . ?
O3 C11 C12 123.25(14) . . ?
O3 C11 C10 116.92(13) . . ?
C12 C11 C10 119.83(14) . . ?
C13 C12 C11 120.07(15) . . ?
C14 C13 C12 120.79(14) . . ?
C13 C14 C15 119.41(15) . . ?
C14 C15 C10 121.26(15) . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        67.49
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.239
_refine_diff_density_min         -0.154
_refine_diff_density_rms         0.040
####################################################################### 
# 
# 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_cu-2897
_database_code_depnum_ccdc_archive 'CCDC 2044596'
loop_
_audit_author_name
_audit_author_address
'Elisabeth Irran'
;Fakultat II Institutfur Chemie, Technische Universitat, Berlin
Germany
;
_audit_update_record             
;
2020-11-16 deposited with the CCDC.	2021-04-05 downloaded from the CCDC.
;

_audit_creation_method           'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H13 N O3'
_chemical_formula_weight         267.27

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   P21/c

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                   7.6398(10)
_cell_length_b                   12.740(2)
_cell_length_c                   13.6472(19)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.618(13)
_cell_angle_gamma                90.00
_cell_volume                     1309.6(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    828
_cell_measurement_theta_min      4.6930
_cell_measurement_theta_max      71.3620

_exptl_crystal_description       rod
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.356
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             560
_exptl_absorpt_coefficient_mu    0.773
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8465
_exptl_absorpt_correction_T_max  0.9386
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150.00(10)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Atlas'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.5435
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4809
_diffrn_reflns_av_R_equivalents  0.0394
_diffrn_reflns_av_sigmaI/netI    0.0465
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         4.78
_diffrn_reflns_theta_max         67.50
_reflns_number_total             2349
_reflns_number_gt                1560
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_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)+(0.0715P)²+0.4692P] 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         2349
_refine_ls_number_parameters     185
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0942
_refine_ls_R_factor_gt           0.0638
_refine_ls_wR_factor_ref         0.1739
_refine_ls_wR_factor_gt          0.1526
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_restrained_S_all      1.087
_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
N1 N 0.0875(3) 0.5981(2) 0.42415(18) 0.0522(7) Uani 1 1 d . . .
O1 O 0.2128(2) 0.64878(18) 0.49387(14) 0.0512(6) Uani 1 1 d . . .
O2 O 0.7294(3) 0.62656(19) 0.43583(15) 0.0542(6) Uani 1 1 d . . .
H2 H 0.854(5) 0.623(3) 0.441(2) 0.065 Uiso 1 1 d . . .
O3 O 0.3033(3) 0.5046(2) 0.18296(16) 0.0612(7) Uani 1 1 d . . .
C1 C 0.3778(4) 0.6344(2) 0.4688(2) 0.0427(7) Uani 1 1 d . . .
C2 C 0.3592(4) 0.5750(2) 0.3849(2) 0.0458(7) Uani 1 1 d . . .
H2A H 0.4510 0.5524 0.3507 0.055 Uiso 1 1 calc R . .
C3 C 0.1746(4) 0.5533(2) 0.3588(2) 0.0444(7) Uani 1 1 d . . .
C4 C 0.5213(4) 0.6855(2) 0.53446(19) 0.0434(7) Uani 1 1 d . . .
C5 C 0.4893(4) 0.7406(3) 0.6185(2) 0.0562(9) Uani 1 1 d . . .
H5A H 0.3711 0.7455 0.6314 0.067 Uiso 1 1 calc R . .
C6 C 0.6240(5) 0.7878(3) 0.6831(2) 0.0629(9) Uani 1 1 d . . .
H6A H 0.5989 0.8237 0.7403 0.075 Uiso 1 1 calc R . .
C7 C 0.7968(4) 0.7826(3) 0.6641(2) 0.0577(9) Uani 1 1 d . . .
H7A H 0.8907 0.8150 0.7082 0.069 Uiso 1 1 calc R . .
C8 C 0.8318(4) 0.7302(3) 0.5809(2) 0.0506(8) Uani 1 1 d . . .
H8A H 0.9497 0.7283 0.5673 0.061 Uiso 1 1 calc R . .
C9 C 0.6981(4) 0.6805(2) 0.5173(2) 0.0436(7) Uani 1 1 d . . .
C10 C 0.0745(4) 0.4908(2) 0.2786(2) 0.0466(7) Uani 1 1 d . . .
C11 C -0.0937(4) 0.4525(3) 0.2888(2) 0.0542(8) Uani 1 1 d . . .
H11A H -0.1390 0.4675 0.3480 0.065 Uiso 1 1 calc R . .
C12 C -0.1943(5) 0.3943(3) 0.2163(3) 0.0655(10) Uani 1 1 d . . .
H12A H -0.3077 0.3695 0.2255 0.079 Uiso 1 1 calc R . .
C13 C -0.1303(5) 0.3716(3) 0.1294(3) 0.0728(11) Uani 1 1 d . . .
H13A H -0.2005 0.3319 0.0784 0.087 Uiso 1 1 calc R . .
C14 C 0.0367(5) 0.4069(3) 0.1170(3) 0.0662(10) Uani 1 1 d . . .
H14A H 0.0815 0.3905 0.0580 0.079 Uiso 1 1 calc R . .
C15 C 0.1383(4) 0.4663(3) 0.1909(2) 0.0547(8) Uani 1 1 d . . .
C16 C 0.3745(5) 0.4754(4) 0.0962(3) 0.0734(11) Uani 1 1 d . . .
H16A H 0.4912 0.5082 0.0984 0.110 Uiso 1 1 calc R . .
H16B H 0.2943 0.4992 0.0367 0.110 Uiso 1 1 calc R . .
H16C H 0.3869 0.3989 0.0941 0.110 Uiso 1 1 calc R . .

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
N1 0.0360(13) 0.0716(19) 0.0526(14) -0.0046(13) 0.0179(11) -0.0008(13)
O1 0.0321(10) 0.0741(15) 0.0518(11) -0.0066(10) 0.0196(9) 0.0024(10)
O2 0.0328(11) 0.0824(17) 0.0514(11) -0.0097(11) 0.0185(9) -0.0002(11)
O3 0.0477(13) 0.0846(17) 0.0570(12) -0.0144(11) 0.0253(10) -0.0103(12)
C1 0.0333(14) 0.0526(18) 0.0462(15) 0.0064(13) 0.0182(11) 0.0035(13)
C2 0.0365(15) 0.0558(19) 0.0499(16) 0.0045(14) 0.0206(12) 0.0035(14)
C3 0.0370(15) 0.0502(18) 0.0502(15) 0.0071(14) 0.0192(12) 0.0016(13)
C4 0.0377(16) 0.0518(18) 0.0432(14) 0.0043(13) 0.0142(12) 0.0031(13)
C5 0.0451(18) 0.075(2) 0.0527(16) -0.0046(16) 0.0201(14) 0.0072(17)
C6 0.054(2) 0.079(3) 0.0570(18) -0.0198(18) 0.0155(15) 0.0060(18)
C7 0.0462(18) 0.066(2) 0.0599(18) -0.0070(17) 0.0057(14) -0.0017(16)
C8 0.0408(16) 0.062(2) 0.0512(16) 0.0062(15) 0.0137(13) 0.0046(15)
C9 0.0388(16) 0.0531(18) 0.0415(14) 0.0039(13) 0.0141(12) 0.0051(13)
C10 0.0367(16) 0.0516(18) 0.0524(16) 0.0031(14) 0.0102(12) -0.0002(14)
C11 0.0391(17) 0.057(2) 0.068(2) 0.0055(17) 0.0139(14) -0.0005(15)
C12 0.0439(19) 0.067(2) 0.086(2) 0.003(2) 0.0107(17) -0.0075(17)
C13 0.060(2) 0.072(3) 0.083(3) -0.016(2) 0.0026(19) -0.011(2)
C14 0.056(2) 0.078(3) 0.066(2) -0.0175(19) 0.0138(16) -0.0033(19)
C15 0.0435(17) 0.062(2) 0.0605(18) -0.0022(16) 0.0133(14) 0.0005(16)
C16 0.057(2) 0.111(3) 0.0581(19) -0.018(2) 0.0268(16) 0.001(2)

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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 C3 1.327(4) . ?
N1 O1 1.391(3) . ?
O1 C1 1.373(3) . ?
O2 C9 1.362(3) . ?
O3 C15 1.372(4) . ?
O3 C16 1.433(4) . ?
C1 C2 1.359(4) . ?
C1 C4 1.450(4) . ?
C2 C3 1.423(4) . ?
C3 C10 1.462(4) . ?
C4 C5 1.401(4) . ?
C4 C9 1.410(4) . ?
C5 C6 1.376(5) . ?
C6 C7 1.390(5) . ?
C7 C8 1.381(4) . ?
C8 C9 1.379(4) . ?
C10 C15 1.400(4) . ?
C10 C11 1.403(4) . ?
C11 C12 1.365(5) . ?
C12 C13 1.388(5) . ?
C13 C14 1.390(5) . ?
C14 C15 1.389(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 N1 O1 107.1(2) . . ?
C1 O1 N1 108.8(2) . . ?
C15 O3 C16 117.0(3) . . ?
C2 C1 O1 108.2(2) . . ?
C2 C1 C4 137.1(2) . . ?
O1 C1 C4 114.7(2) . . ?
C1 C2 C3 106.2(2) . . ?
N1 C3 C2 109.6(3) . . ?
N1 C3 C10 118.6(2) . . ?
C2 C3 C10 131.8(2) . . ?
C5 C4 C9 117.5(3) . . ?
C5 C4 C1 120.9(3) . . ?
C9 C4 C1 121.6(2) . . ?
C6 C5 C4 122.0(3) . . ?
C5 C6 C7 119.4(3) . . ?
C8 C7 C6 119.8(3) . . ?
C9 C8 C7 121.0(3) . . ?
O2 C9 C8 122.2(3) . . ?
O2 C9 C4 117.5(3) . . ?
C8 C9 C4 120.3(3) . . ?
C15 C10 C11 117.6(3) . . ?
C15 C10 C3 123.2(3) . . ?
C11 C10 C3 119.2(3) . . ?
C12 C11 C10 122.1(3) . . ?
C11 C12 C13 119.8(3) . . ?
C12 C13 C14 119.8(3) . . ?
C15 C14 C13 120.1(3) . . ?
O3 C15 C14 123.0(3) . . ?
O3 C15 C10 116.4(3) . . ?
C14 C15 C10 120.6(3) . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        67.50
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.220
_refine_diff_density_min         -0.264
_refine_diff_density_rms         0.055
####################################################################### 
# 
# 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_cu-2905a
_database_code_depnum_ccdc_archive 'CCDC 2044598'
loop_
_audit_author_name
_audit_author_address
'Elisabeth Irran'
;Fakultat II Institutfur Chemie, Technische Universitat, Berlin
Germany
;
_audit_update_record             
;
2020-11-16 deposited with the CCDC.	2021-04-05 downloaded from the CCDC.
;

_audit_creation_method           'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C16 H13 N O3'
_chemical_formula_weight         267.27

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   Pca21

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

_cell_length_a                   25.2543(10)
_cell_length_b                   5.1328(2)
_cell_length_c                   9.8457(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1276.25(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    1919
_cell_measurement_theta_min      3.4350
_cell_measurement_theta_max      72.5230

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.391
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             560
_exptl_absorpt_coefficient_mu    0.794
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7708
_exptl_absorpt_correction_T_max  0.9659
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150.00(10)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, Atlas'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.5435
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            4293
_diffrn_reflns_av_R_equivalents  0.0259
_diffrn_reflns_av_sigmaI/netI    0.0257
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.50
_diffrn_reflns_theta_max         67.36
_reflns_number_total             1900
_reflns_number_gt                1734
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_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)+(0.0712P)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   0.2(3)
_refine_ls_number_reflns         1900
_refine_ls_number_parameters     185
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0462
_refine_ls_R_factor_gt           0.0417
_refine_ls_wR_factor_ref         0.1109
_refine_ls_wR_factor_gt          0.1054
_refine_ls_goodness_of_fit_ref   1.099
_refine_ls_restrained_S_all      1.099
_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
O1 O 0.52564(6) 0.4693(3) 0.86639(17) 0.0436(4) Uani 1 1 d . . .
O2 O 0.64824(8) -0.0237(4) 0.8872(2) 0.0529(5) Uani 1 1 d . . .
H2 H 0.6166(14) 0.029(6) 0.908(4) 0.064 Uiso 1 1 d . . .
O3 O 0.35356(6) 1.3407(3) 0.75429(19) 0.0470(4) Uani 1 1 d . . .
N1 N 0.57155(8) 0.3174(4) 0.8525(2) 0.0437(5) Uani 1 1 d . . .
C1 C 0.59594(9) 0.4016(5) 0.7427(3) 0.0387(5) Uani 1 1 d . . .
C2 C 0.56659(9) 0.6062(5) 0.6808(2) 0.0388(5) Uani 1 1 d . . .
H2A H 0.5752 0.6988 0.6002 0.047 Uiso 1 1 calc R . .
C3 C 0.52402(9) 0.6403(4) 0.7610(2) 0.0375(5) Uani 1 1 d . . .
C4 C 0.64547(9) 0.2790(5) 0.6973(3) 0.0399(5) Uani 1 1 d . . .
C5 C 0.66863(10) 0.0713(5) 0.7709(3) 0.0449(6) Uani 1 1 d . . .
C6 C 0.71452(10) -0.0452(5) 0.7215(3) 0.0520(7) Uani 1 1 d . . .
H6A H 0.7299 -0.1864 0.7699 0.062 Uiso 1 1 calc R . .
C7 C 0.73795(10) 0.0409(5) 0.6038(3) 0.0542(7) Uani 1 1 d . . .
H7A H 0.7691 -0.0418 0.5712 0.065 Uiso 1 1 calc R . .
C8 C 0.71615(9) 0.2492(5) 0.5319(3) 0.0516(7) Uani 1 1 d . . .
H8A H 0.7324 0.3101 0.4509 0.062 Uiso 1 1 calc R . .
C9 C 0.67072(10) 0.3653(5) 0.5801(3) 0.0451(6) Uani 1 1 d . . .
H9A H 0.6562 0.5086 0.5318 0.054 Uiso 1 1 calc R . .
C10 C 0.47904(9) 0.8205(4) 0.7584(2) 0.0358(5) Uani 1 1 d . . .
C11 C 0.47421(9) 0.9939(5) 0.6503(3) 0.0404(5) Uani 1 1 d . . .
H11A H 0.4995 0.9898 0.5790 0.048 Uiso 1 1 calc R . .
C12 C 0.43291(9) 1.1730(4) 0.6449(3) 0.0397(5) Uani 1 1 d . . .
H12A H 0.4300 1.2909 0.5709 0.048 Uiso 1 1 calc R . .
C13 C 0.39605(8) 1.1767(4) 0.7491(3) 0.0386(5) Uani 1 1 d . . .
C14 C 0.40048(9) 1.0042(4) 0.8569(3) 0.0411(6) Uani 1 1 d . . .
H14A H 0.3751 1.0080 0.9282 0.049 Uiso 1 1 calc R . .
C15 C 0.44134(9) 0.8280(4) 0.8611(2) 0.0393(5) Uani 1 1 d . . .
H15A H 0.4439 0.7099 0.9351 0.047 Uiso 1 1 calc R . .
C16 C 0.34721(10) 1.5199(5) 0.6434(3) 0.0497(6) Uani 1 1 d . . .
H16A H 0.3169 1.6340 0.6613 0.075 Uiso 1 1 calc R . .
H16B H 0.3411 1.4224 0.5593 0.075 Uiso 1 1 calc R . .
H16C H 0.3793 1.6255 0.6340 0.075 Uiso 1 1 calc R . .

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
O1 0.0485(9) 0.0458(10) 0.0365(9) 0.0046(8) -0.0001(7) 0.0048(7)
O2 0.0578(11) 0.0498(11) 0.0512(12) 0.0063(9) -0.0031(9) 0.0069(9)
O3 0.0514(9) 0.0370(9) 0.0527(11) -0.0009(8) 0.0026(8) 0.0042(7)
N1 0.0478(11) 0.0441(11) 0.0392(10) 0.0000(9) -0.0030(9) 0.0054(9)
C1 0.0429(11) 0.0386(11) 0.0345(11) -0.0039(11) -0.0063(9) -0.0047(10)
C2 0.0449(12) 0.0359(11) 0.0355(11) 0.0019(10) -0.0008(9) -0.0035(10)
C3 0.0478(12) 0.0326(11) 0.0322(12) -0.0008(10) -0.0065(9) -0.0048(9)
C4 0.0426(12) 0.0375(12) 0.0397(12) -0.0060(10) -0.0069(9) -0.0035(10)
C5 0.0504(13) 0.0385(13) 0.0458(14) -0.0026(11) -0.0087(11) -0.0036(10)
C6 0.0499(14) 0.0411(14) 0.0649(19) -0.0050(14) -0.0092(13) 0.0020(11)
C7 0.0434(13) 0.0487(15) 0.0706(19) -0.0125(14) -0.0016(13) 0.0003(11)
C8 0.0450(12) 0.0542(16) 0.0557(16) -0.0071(14) 0.0011(11) -0.0083(12)
C9 0.0441(13) 0.0431(14) 0.0480(14) -0.0040(11) -0.0047(11) -0.0035(10)
C10 0.0417(11) 0.0335(11) 0.0324(12) -0.0021(10) -0.0034(9) -0.0054(8)
C11 0.0443(12) 0.0408(12) 0.0361(13) 0.0018(10) 0.0026(10) -0.0023(10)
C12 0.0494(12) 0.0323(12) 0.0373(12) 0.0017(10) -0.0022(10) -0.0042(9)
C13 0.0427(12) 0.0301(11) 0.0429(13) -0.0051(11) -0.0033(10) -0.0040(9)
C14 0.0471(13) 0.0358(12) 0.0404(13) -0.0031(11) 0.0041(11) -0.0052(9)
C15 0.0491(12) 0.0337(11) 0.0352(12) 0.0015(10) 0.0003(11) -0.0066(10)
C16 0.0560(15) 0.0419(14) 0.0514(15) -0.0041(13) -0.0101(12) 0.0075(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
O1 C3 1.360(3) . ?
O1 N1 1.404(3) . ?
O2 C5 1.347(3) . ?
O3 C13 1.365(3) . ?
O3 C16 1.436(4) . ?
N1 C1 1.317(3) . ?
C1 C2 1.423(4) . ?
C1 C4 1.470(3) . ?
C2 C3 1.345(3) . ?
C3 C10 1.465(3) . ?
C4 C9 1.391(4) . ?
C4 C5 1.415(4) . ?
C5 C6 1.392(4) . ?
C6 C7 1.374(4) . ?
C7 C8 1.396(4) . ?
C8 C9 1.377(4) . ?
C10 C15 1.390(3) . ?
C10 C11 1.393(4) . ?
C11 C12 1.391(3) . ?
C12 C13 1.385(3) . ?
C13 C14 1.387(4) . ?
C14 C15 1.373(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
C3 O1 N1 108.01(18) . . ?
C13 O3 C16 117.0(2) . . ?
C1 N1 O1 106.5(2) . . ?
N1 C1 C2 110.5(2) . . ?
N1 C1 C4 120.5(2) . . ?
C2 C1 C4 129.0(2) . . ?
C3 C2 C1 105.1(2) . . ?
C2 C3 O1 109.9(2) . . ?
C2 C3 C10 133.7(2) . . ?
O1 C3 C10 116.38(19) . . ?
C9 C4 C5 118.4(2) . . ?
C9 C4 C1 120.4(2) . . ?
C5 C4 C1 121.2(2) . . ?
O2 C5 C6 117.4(2) . . ?
O2 C5 C4 123.4(2) . . ?
C6 C5 C4 119.3(3) . . ?
C7 C6 C5 121.0(3) . . ?
C6 C7 C8 120.3(2) . . ?
C9 C8 C7 119.0(3) . . ?
C8 C9 C4 122.0(3) . . ?
C15 C10 C11 118.6(2) . . ?
C15 C10 C3 122.4(2) . . ?
C11 C10 C3 119.0(2) . . ?
C12 C11 C10 121.1(2) . . ?
C13 C12 C11 119.0(2) . . ?
O3 C13 C12 124.4(2) . . ?
O3 C13 C14 115.4(2) . . ?
C12 C13 C14 120.2(2) . . ?
C15 C14 C13 120.3(2) . . ?
C14 C15 C10 120.7(2) . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        67.36
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.197
_refine_diff_density_min         -0.157
_refine_diff_density_rms         0.047
