# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2023

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

data_exp_1871
_database_code_depnum_ccdc_archive 'CCDC 2246131'
loop_
_audit_author_name
_audit_author_address
'Ikyon Kim'
;Yonsei University
South Korea
;
_audit_update_record             
;
2023-03-03 deposited with the CCDC.	2023-04-18 downloaded from the CCDC.
;
_audit_creation_date             2022-12-28
_audit_creation_method           
;
Olex2 1.2-ac21
(compiled 2015.09.16 svn.r134, GUI svn.r4998)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H13 N3 O'
_chemical_formula_sum            'C16 H13 N3 O'
_chemical_formula_weight         263.29
_chemical_melting_point          ?
_chemical_oxdiff_formula         C17H11N3O
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'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.7205(14)
_cell_length_b                   13.737(3)
_cell_length_c                   11.3839(19)
_cell_angle_alpha                90
_cell_angle_beta                 100.158(16)
_cell_angle_gamma                90
_cell_volume                     1342.4(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1055
_cell_measurement_temperature    293.9(7)
_cell_measurement_theta_max      24.1660
_cell_measurement_theta_min      2.7820
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.34219
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.29d (Rigaku Oxford Diffraction, 2017)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.303
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0734
_diffrn_reflns_av_unetI/netI     0.1328
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.816
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            6480
_diffrn_reflns_point_group_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.816
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.531
_diffrn_reflns_theta_min         2.346
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      293.9(7)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4525
_diffrn_detector_type            AtlasS2
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.816
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -19.00  29.00   4.00  978.54    --  -11.04 -99.00  90.00   12
  2  ω    -62.00  78.00   4.00  978.54    --   11.83   0.00-150.00   35
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, AtlasS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0290118000
_diffrn_orient_matrix_UB_12      0.0270877000
_diffrn_orient_matrix_UB_13      -0.0521635000
_diffrn_orient_matrix_UB_21      0.0140843000
_diffrn_orient_matrix_UB_22      0.0438710000
_diffrn_orient_matrix_UB_23      0.0330479000
_diffrn_orient_matrix_UB_31      0.0761101000
_diffrn_orient_matrix_UB_32      0.0022103000
_diffrn_orient_matrix_UB_33      -0.0139240000
_diffrn_oxdiff_ac3_digest_frames 
;
01f46a7e864eb5ea0c31b6dbf2790275c000046f3fd
;
_diffrn_oxdiff_ac3_digest_hkl    
;
01a8115707e11a60b5e3a6165ba922371feb3b
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1324
_reflns_number_total             3057
_reflns_odcompleteness_completeness 97.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_data_collection       'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_data_reduction        'CrysAlisPro 1.171.39.29d (Rigaku OD, 2017)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.328
_refine_diff_density_min         -0.404
_refine_diff_density_rms         0.061
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     183
_refine_ls_number_reflns         3057
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1816
_refine_ls_R_factor_gt           0.0778
_refine_ls_restrained_S_all      1.009
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0860P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1788
_refine_ls_wR_factor_ref         0.2429
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Rotating group:
 N003(H00A,H00B)
2.b Aromatic/amide H refined with riding coordinates:
 C00A(H00C), C00C(H00D), C00E(H00E), C00F(H00F), C00G(H00G), C00H(H00H),
 C00I(H00I), C00J(H00J)
2.c Idealised Me refined as rotating group:
 C00K(H00K,H00L,H00M)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N001 N 0.4483(3) 0.0722(2) 0.3655(2) 0.0365(7) Uani 1 1 d . . . . .
O002 O 0.2031(3) 0.6020(2) 0.4879(2) 0.0595(8) Uani 1 1 d . . . . .
N003 N 0.5992(3) 0.2202(2) 0.3806(3) 0.0512(9) Uani 1 1 d . . . . .
H00A H 0.675583 0.180475 0.401323 0.061 Uiso 1 1 d GR . . . .
H00B H 0.599258 0.239606 0.308603 0.061 Uiso 1 1 d GR . . . .
C004 C 0.4615(4) 0.1714(3) 0.3869(3) 0.0370(8) Uani 1 1 d . . . . .
C005 C 0.2944(4) 0.0421(3) 0.3702(3) 0.0355(8) Uani 1 1 d . . . . .
C006 C 0.2142(4) 0.1259(3) 0.3923(3) 0.0385(9) Uani 1 1 d . . . . .
C007 C 0.0585(4) 0.1252(3) 0.4086(3) 0.0401(9) Uani 1 1 d . . . . .
N008 N -0.0710(4) 0.1250(2) 0.4207(3) 0.0617(10) Uani 1 1 d . . . . .
C009 C 0.3191(4) 0.2064(3) 0.4043(3) 0.0374(9) Uani 1 1 d . . . . .
C00A C 0.5597(4) 0.0069(3) 0.3427(3) 0.0427(9) Uani 1 1 d . . . . .
H00C H 0.660264 0.028095 0.339638 0.051 Uiso 1 1 calc R . . . .
C00B C 0.2824(4) 0.3084(3) 0.4273(3) 0.0389(9) Uani 1 1 d . . . . .
C00C C 0.2593(4) -0.0564(3) 0.3533(3) 0.0437(9) Uani 1 1 d . . . . .
H00D H 0.159458 -0.078438 0.357128 0.052 Uiso 1 1 calc R . . . .
C00D C 0.2203(4) 0.5061(3) 0.4642(3) 0.0429(9) Uani 1 1 d . . . . .
C00E C 0.1638(4) 0.3580(3) 0.3539(3) 0.0465(9) Uani 1 1 d . . . . .
H00E H 0.103096 0.324812 0.291106 0.056 Uiso 1 1 calc R . . . .
C00F C 0.5222(4) -0.0870(3) 0.3251(3) 0.0460(10) Uani 1 1 d . . . . .
H00F H 0.596803 -0.130794 0.308626 0.055 Uiso 1 1 calc R . . . .
C00G C 0.1333(4) 0.4555(3) 0.3713(3) 0.0500(10) Uani 1 1 d . . . . .
H00G H 0.053726 0.486879 0.319980 0.060 Uiso 1 1 calc R . . . .
C00H C 0.3694(4) -0.1208(3) 0.3313(3) 0.0494(10) Uani 1 1 d . . . . .
H00H H 0.345028 -0.186415 0.320333 0.059 Uiso 1 1 calc R . . . .
C00I C 0.3668(4) 0.3609(3) 0.5220(3) 0.0512(10) Uani 1 1 d . . . . .
H00I H 0.445768 0.329717 0.574131 0.061 Uiso 1 1 calc R . . . .
C00J C 0.3371(4) 0.4565(3) 0.5405(3) 0.0538(11) Uani 1 1 d . . . . .
H00J H 0.395430 0.489119 0.604880 0.065 Uiso 1 1 calc R . . . .
C00K C 0.0895(5) 0.6557(3) 0.4091(4) 0.0643(12) Uani 1 1 d . . . . .
H00K H 0.115486 0.655415 0.330584 0.096 Uiso 1 1 calc GR . . . .
H00L H 0.087202 0.721506 0.436982 0.096 Uiso 1 1 calc GR . . . .
H00M H -0.010996 0.626358 0.406441 0.096 Uiso 1 1 calc GR . . . .


_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
N001 C004 1.386(5) . ?
N001 C005 1.415(4) . ?
N001 C00A 1.379(4) . ?
O002 C00D 1.358(4) . ?
O002 C00K 1.420(4) . ?
N003 C004 1.388(4) . ?
C004 C009 1.378(4) . ?
C005 C006 1.392(5) . ?
C005 C00C 1.394(5) . ?
C006 C007 1.403(5) . ?
C006 C009 1.426(5) . ?
C007 N008 1.161(4) . ?
C009 C00B 1.471(5) . ?
C00A C00F 1.337(5) . ?
C00B C00E 1.388(5) . ?
C00B C00I 1.395(5) . ?
C00C C00H 1.360(5) . ?
C00D C00G 1.376(5) . ?
C00D C00J 1.394(5) . ?
C00E C00G 1.388(5) . ?
C00F C00H 1.424(5) . ?
C00I C00J 1.362(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
C004 N001 C005 109.2(3) . . ?
C00A N001 C004 129.3(3) . . ?
C00A N001 C005 121.5(3) . . ?
C00D O002 C00K 117.9(3) . . ?
N001 C004 N003 120.8(3) . . ?
C009 C004 N001 108.7(3) . . ?
C009 C004 N003 130.4(4) . . ?
C006 C005 N001 106.0(3) . . ?
C006 C005 C00C 136.3(3) . . ?
C00C C005 N001 117.7(3) . . ?
C005 C006 C007 123.2(3) . . ?
C005 C006 C009 108.9(3) . . ?
C007 C006 C009 127.7(3) . . ?
N008 C007 C006 179.1(4) . . ?
C004 C009 C006 107.2(3) . . ?
C004 C009 C00B 126.0(3) . . ?
C006 C009 C00B 126.8(3) . . ?
C00F C00A N001 119.5(3) . . ?
C00E C00B C009 121.5(3) . . ?
C00E C00B C00I 116.6(4) . . ?
C00I C00B C009 121.9(3) . . ?
C00H C00C C005 120.8(3) . . ?
O002 C00D C00G 125.2(3) . . ?
O002 C00D C00J 116.4(3) . . ?
C00G C00D C00J 118.4(4) . . ?
C00G C00E C00B 122.0(3) . . ?
C00A C00F C00H 120.9(3) . . ?
C00D C00G C00E 120.2(3) . . ?
C00C C00H C00F 119.6(4) . . ?
C00J C00I C00B 121.9(3) . . ?
C00I C00J C00D 120.9(4) . . ?

_shelx_SHELXL_version_number     2018/3
_olex2_date_sample_data_collection 2022-12-26
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.393
_oxdiff_exptl_absorpt_empirical_full_min 0.505
####################################################################### 
# 
# 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_KWJ2143
_database_code_depnum_ccdc_archive 'CCDC 2246132'
loop_
_audit_author_name
_audit_author_address
'Ikyon Kim'
;Yonsei University
South Korea
;
_audit_update_record             
;
2023-03-03 deposited with the CCDC.	2023-04-18 downloaded from the CCDC.
;
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C15 H10 N2 O'
_chemical_formula_iupac          ?
_chemical_formula_weight         234.25

_chemical_melting_point          ?

_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   12.1137(8)
_cell_length_b                   9.2789(7)
_cell_length_c                   21.5088(15)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2417.6(3)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9874
_cell_measurement_theta_min      2.3893
_cell_measurement_theta_max      28.0967
_cell_measurement_temperature    296.(2)

_exptl_crystal_description       Block
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.400
_exptl_crystal_size_min          0.350
_exptl_crystal_density_diffrn    1.287
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             976

_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.85
_exptl_absorpt_correction_T_max  0.97

_exptl_special_details           
;
;

_diffrn_ambient_temperature      296.(2)

_diffrn_source                   ?
_diffrn_source_type              ?

_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  ?

_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            95310
_diffrn_reflns_av_R_equivalents  0.0509
_diffrn_reflns_av_unetI/netI     0.0139
_diffrn_reflns_theta_min         1.89
_diffrn_reflns_theta_max         28.17
_diffrn_reflns_theta_full        28.17
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28

_refine_special_details          
;
;

_reflns_number_total             2964
_reflns_number_gt                2186
_reflns_threshold_expression     'I > 2σ(I)'

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0705
_refine_ls_R_factor_gt           0.0468
_refine_ls_wR_factor_gt          0.1025
_refine_ls_wR_factor_ref         0.1205
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_restrained_S_all      1.074
_refine_ls_number_reflns         2964
_refine_ls_number_parameters     163
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0383P)²+0.9253P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.199
_refine_diff_density_min         -0.207
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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'

_computing_data_collection       'Bruker Instrument Service v2019.11.0.3'
_computing_cell_refinement       'SAINT V8.40A (Bruker Nano, Inc., 2019)'
_computing_data_reduction        'SAINT V8.40A (Bruker Nano, Inc., 2019)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2017)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.31248(9) 0.67997(12) 0.41921(6) 0.0580(3) Uani d . . . 1 . .
N N1 0.28550(10) 0.29862(15) 0.25472(6) 0.0529(3) Uani d . . . 1 . .
C C9 0.23456(12) 0.45606(16) 0.33810(6) 0.0417(3) Uani d . . . 1 . .
C C11 0.20225(11) 0.35391(16) 0.28813(7) 0.0421(3) Uani d . . . 1 . .
C C6 0.49344(12) 0.58556(16) 0.42001(6) 0.0423(3) Uani d . . . 1 . .
C C7 0.37668(12) 0.59056(16) 0.39897(6) 0.0432(3) Uani d . . . 1 . .
C C8 0.33982(12) 0.48636(16) 0.35091(7) 0.0450(3) Uani d . . . 1 . .
H H8 0.393928 0.438811 0.328098 0.054 Uiso calc U . R 1 . .
C C12 0.09301(12) 0.31870(17) 0.27673(7) 0.0494(4) Uani d . . . 1 . .
H H12 0.036802 0.359557 0.300323 0.059 Uiso calc U . R 1 . .
C C5 0.56359(13) 0.47308(19) 0.40527(8) 0.0534(4) Uani d . . . 1 . .
H H5 0.538498 0.397585 0.380588 0.064 Uiso calc U . R 1 . .
C C10 0.14459(13) 0.51887(18) 0.37268(8) 0.0521(4) Uani d . . . 1 . .
C C1 0.53208(14) 0.69590(18) 0.45781(8) 0.0558(4) Uani d . . . 1 . .
H H1 0.485578 0.771762 0.468417 0.067 Uiso calc U . R 1 . .
N N2 0.06729(13) 0.5606(2) 0.39660(8) 0.0806(5) Uani d . . . 1 . .
C C14 0.15306(14) 0.16503(19) 0.19563(8) 0.0582(4) Uani d . . . 1 . .
H H14 0.139053 0.099912 0.163724 0.07 Uiso calc U . R 1 . .
C C13 0.06870(13) 0.22216(19) 0.22987(8) 0.0565(4) Uani d . . . 1 . .
H H13 -0.004056 0.196361 0.221706 0.068 Uiso calc U . R 1 . .
C C15 0.25934(15) 0.2064(2) 0.20964(8) 0.0590(4) Uani d . . . 1 . .
H H15 0.316463 0.167546 0.186119 0.071 Uiso calc U . R 1 . .
C C4 0.67104(15) 0.4725(2) 0.42714(9) 0.0644(5) Uani d . . . 1 . .
H H4 0.718315 0.397333 0.416724 0.077 Uiso calc U . R 1 . .
C C3 0.70780(15) 0.5828(2) 0.46415(8) 0.0659(5) Uani d . . . 1 . .
H H3 0.780056 0.582236 0.478769 0.079 Uiso calc U . R 1 . .
C C2 0.63885(16) 0.6936(2) 0.47967(8) 0.0655(5) Uani d . . . 1 . .
H H2 0.664121 0.767635 0.505083 0.079 Uiso calc U . R 1 . .


_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C7 . 1.2176(18) ?
N1 C15 . 1.331(2) ?
N1 C11 . 1.3403(19) ?
C9 C8 . 1.335(2) ?
C9 C10 . 1.442(2) ?
C9 C11 . 1.486(2) ?
C11 C12 . 1.385(2) ?
C6 C5 . 1.383(2) ?
C6 C1 . 1.389(2) ?
C6 C7 . 1.486(2) ?
C7 C8 . 1.484(2) ?
C8 H8 . 0.93 ?
C12 C13 . 1.380(2) ?
C12 H12 . 0.93 ?
C5 C4 . 1.384(2) ?
C5 H5 . 0.93 ?
C10 N2 . 1.137(2) ?
C1 C2 . 1.376(2) ?
C1 H1 . 0.93 ?
C14 C13 . 1.367(2) ?
C14 C15 . 1.377(2) ?
C14 H14 . 0.93 ?
C13 H13 . 0.93 ?
C15 H15 . 0.93 ?
C4 C3 . 1.371(3) ?
C4 H4 . 0.93 ?
C3 C2 . 1.366(3) ?
C3 H3 . 0.93 ?
C2 H2 . 0.93 ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C15 N1 C11 . . 117.22(14) ?
C8 C9 C10 . . 122.03(14) ?
C8 C9 C11 . . 122.38(13) ?
C10 C9 C11 . . 115.58(13) ?
N1 C11 C12 . . 122.26(14) ?
N1 C11 C9 . . 115.71(12) ?
C12 C11 C9 . . 122.03(13) ?
C5 C6 C1 . . 118.92(14) ?
C5 C6 C7 . . 122.60(14) ?
C1 C6 C7 . . 118.44(14) ?
O1 C7 C8 . . 120.06(14) ?
O1 C7 C6 . . 121.35(14) ?
C8 C7 C6 . . 118.57(13) ?
C9 C8 C7 . . 124.64(14) ?
C9 C8 H8 . . 117.7 ?
C7 C8 H8 . . 117.7 ?
C13 C12 C11 . . 119.10(15) ?
C13 C12 H12 . . 120.5 ?
C11 C12 H12 . . 120.5 ?
C6 C5 C4 . . 120.19(16) ?
C6 C5 H5 . . 119.9 ?
C4 C5 H5 . . 119.9 ?
N2 C10 C9 . . 173.57(18) ?
C2 C1 C6 . . 120.34(17) ?
C2 C1 H1 . . 119.8 ?
C6 C1 H1 . . 119.8 ?
C13 C14 C15 . . 118.23(15) ?
C13 C14 H14 . . 120.9 ?
C15 C14 H14 . . 120.9 ?
C14 C13 C12 . . 119.06(15) ?
C14 C13 H13 . . 120.5 ?
C12 C13 H13 . . 120.5 ?
N1 C15 C14 . . 124.14(16) ?
N1 C15 H15 . . 117.9 ?
C14 C15 H15 . . 117.9 ?
C3 C4 C5 . . 120.00(18) ?
C3 C4 H4 . . 120.0 ?
C5 C4 H4 . . 120.0 ?
C2 C3 C4 . . 120.33(17) ?
C2 C3 H3 . . 119.8 ?
C4 C3 H3 . . 119.8 ?
C3 C2 C1 . . 120.21(17) ?
C3 C2 H2 . . 119.9 ?
C1 C2 H2 . . 119.9 ?

