# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2017

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

data_AP-BIN6
_database_code_depnum_ccdc_archive 'CCDC 1535780'
_audit_update_record             
;
2017-03-03 deposited with the CCDC.
2017-06-12 downloaded from the CCDC.
;
_audit_creation_date             2016-12-22
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_chemical_formula_moiety         'C22 H15 N5 O'
_chemical_formula_sum            'C22 H15 N5 O'
_chemical_formula_weight         365.40
_chemical_oxdiff_formula         C23H14N4O2
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_Cromer_Mann_a1
_atom_type_scat_Cromer_Mann_a2
_atom_type_scat_Cromer_Mann_a3
_atom_type_scat_Cromer_Mann_a4
_atom_type_scat_Cromer_Mann_b1
_atom_type_scat_Cromer_Mann_b2
_atom_type_scat_Cromer_Mann_b3
_atom_type_scat_Cromer_Mann_b4
_atom_type_scat_Cromer_Mann_c
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 0.49300 0.32291 0.14019 0.04081 10.51090 26.12570 3.14236
57.79970 0.0030380000826
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 2.31000 1.02000 1.58860 0.86500 20.84390 10.20750 0.56870
51.65120 0.215599998832
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 3.04850 2.28680 1.54630 0.86700 13.27710 5.70110 0.32390
32.90890 0.250800013542
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 12.21260 3.13220 2.01250 1.16630 0.00570 9.89330 28.99750
0.58260 -11.5290002823
'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y,-z+1/2
3 -x,-y,-z
4 x,-y,z-1/2
5 x+1/2,y+1/2,z
6 -x+1/2,y+1/2,-z+1/2
7 -x+1/2,-y+1/2,-z
8 x+1/2,-y+1/2,z-1/2

_symmetry_Int_Tables_number      15
_cell_length_a                   23.175(4)
_cell_length_b                   9.9645(11)
_cell_length_c                   16.245(2)
_cell_angle_alpha                90
_cell_angle_beta                 107.625(18)
_cell_angle_gamma                90
_cell_volume                     3575.2(10)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    1231
_cell_measurement_temperature    294.1(3)
_cell_measurement_theta_max      26.2190
_cell_measurement_theta_min      3.6320
_exptl_absorpt_coefficient_mu    0.088
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.97259
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.3576
_exptl_crystal_description       block
_exptl_crystal_F_000             1520.5969
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.24
_diffrn_reflns_av_R_equivalents  0.0275
_diffrn_reflns_av_unetI/netI     0.0502
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -30
_diffrn_reflns_limit_k_max       5
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            7321
_diffrn_reflns_theta_full        26.3720
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         3.24
_diffrn_ambient_temperature      294.1(3)
_diffrn_detector_area_resol_mean 8.0640
_diffrn_measured_fraction_theta_full 0.9978
_diffrn_measured_fraction_theta_max 0.9978
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   -5.00   24.00   1.0000    7.4100
omega____ theta____ kappa____ phi______ frames
    -      -20.3747  -99.0000  150.0000 29

#__ type_ start__ end____ width___ exp.time_
  2 omega   67.00   93.00   1.0000    7.4100
omega____ theta____ kappa____ phi______ frames
    -       22.7184 -178.0000    0.0000 26

#__ type_ start__ end____ width___ exp.time_
  3 omega   11.00   65.00   1.0000    7.4100
omega____ theta____ kappa____ phi______ frames
    -       22.7184  -99.0000    0.0000 54

#__ type_ start__ end____ width___ exp.time_
  4 omega  -46.00   80.00   1.0000    7.4100
omega____ theta____ kappa____ phi______ frames
    -       22.7184    0.0000  -90.0000 126
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0211362000
_diffrn_orient_matrix_UB_12      -0.0460194000
_diffrn_orient_matrix_UB_13      0.0259820000
_diffrn_orient_matrix_UB_21      0.0159083000
_diffrn_orient_matrix_UB_22      0.0539773000
_diffrn_orient_matrix_UB_23      0.0253935000
_diffrn_orient_matrix_UB_31      -0.0181849000
_diffrn_orient_matrix_UB_32      -0.0062039000
_diffrn_orient_matrix_UB_33      0.0279265000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              27
_reflns_limit_h_min              -28
_reflns_limit_k_max              12
_reflns_limit_k_min              0
_reflns_limit_l_max              20
_reflns_limit_l_min              0
_reflns_number_gt                2365
_reflns_number_total             3646
_reflns_odcompleteness_completeness 99.72
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2013)'
_computing_structure_solution    
;
Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008;
Palatinus et al., 2012)
;
_refine_diff_density_max         0.2934
_refine_diff_density_min         -0.3117
_refine_diff_density_rms         0.0647
_refine_ls_d_res_high            0.8000
_refine_ls_d_res_low             6.2910
_refine_ls_goodness_of_fit_ref   1.0743
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    30
_refine_ls_number_parameters     252
_refine_ls_number_reflns         3646
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0958
_refine_ls_R_factor_gt           0.0552
_refine_ls_restrained_S_all      1.0743
_refine_ls_shift/su_max          0.0004
_refine_ls_shift/su_mean         0.0001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0404P)²+0.7611P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1072
_refine_ls_wR_factor_ref         0.1284
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Ternary CH refined with riding coordinates:
 C2(H2)
2.b Aromatic/amide H refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C8(H8), C14(H14), C15(H15), C16(H16), C17(H17),
 C21(H21), C22(H22), C24(H24), C25(H25), N3(H3), N12(H12)
;
_atom_sites_solution_primary     iterative
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_refinement_flags_posn
C2 C 0.43437(10) 0.2426(2) 0.51116(12) 0.0489(5) Uani 1.000000 .
H2 H 0.45994(10) 0.2762(2) 0.47742(12) 0.0586(6) Uiso 1.000000 R
C4 C 0.33831(11) 0.1232(2) 0.47489(13) 0.0583(6) Uani 1.000000 .
C5 C 0.27615(12) 0.1238(3) 0.43537(16) 0.0812(8) Uani 1.000000 .
H5 H 0.25873(12) 0.1884(3) 0.39394(16) 0.0974(10) Uiso 1.000000 R
C6 C 0.24053(13) 0.0296(4) 0.4573(2) 0.0919(9) Uani 1.000000 .
H6 H 0.19890(13) 0.0306(4) 0.4308(2) 0.1103(11) Uiso 1.000000 R
C7 C 0.26570(14) -0.0669(3) 0.51839(19) 0.0862(9) Uani 1.000000 .
H7 H 0.24117(14) -0.1305(3) 0.53315(19) 0.1035(10) Uiso 1.000000 R
C8 C 0.32664(12) -0.0687(3) 0.55697(16) 0.0707(7) Uani 1.000000 .
H8 H 0.34359(12) -0.1344(3) 0.59774(16) 0.0848(8) Uiso 1.000000 R
C9 C 0.36384(11) 0.0262(2) 0.53635(14) 0.0554(6) Uani 1.000000 .
C10 C 0.42950(11) 0.0172(2) 0.57530(14) 0.0558(6) Uani 1.000000 .
C11 C 0.52544(10) 0.1314(2) 0.59458(13) 0.0490(5) Uani 1.000000 .
C13 C 0.61729(11) 0.0887(2) 0.67561(14) 0.0571(6) Uani 1.000000 .
C14 C 0.67061(13) 0.0409(3) 0.73173(17) 0.0810(8) Uani 1.000000 .
H14 H 0.67155(13) -0.0388(3) 0.76195(17) 0.0972(9) Uiso 1.000000 R
C15 C 0.72179(13) 0.1141(3) 0.74141(19) 0.0901(9) Uani 1.000000 .
H15 H 0.75844(13) 0.0838(3) 0.77844(19) 0.1082(10) Uiso 1.000000 R
C16 C 0.71996(14) 0.2326(3) 0.69703(19) 0.0856(8) Uani 1.000000 .
H16 H 0.75558(14) 0.2807(3) 0.70457(19) 0.1027(10) Uiso 1.000000 R
C17 C 0.66723(12) 0.2811(3) 0.64232(17) 0.0759(7) Uani 1.000000 .
H17 H 0.66657(12) 0.3619(3) 0.61340(17) 0.0911(9) Uiso 1.000000 R
C18 C 0.61512(11) 0.2081(2) 0.63084(14) 0.0544(6) Uani 1.000000 .
C20 C 0.43110(9) 0.35147(19) 0.57533(12) 0.0423(5) Uani 1.000000 .
C21 C 0.43448(9) 0.4839(2) 0.55255(13) 0.0466(5) Uani 1.000000 .
H21 H 0.43997(9) 0.5039(2) 0.49951(13) 0.0560(6) Uiso 1.000000 R
C22 C 0.42997(9) 0.5860(2) 0.60596(13) 0.0486(5) Uani 1.000000 .
H22 H 0.43231(9) 0.6747(2) 0.58961(13) 0.0583(6) Uiso 1.000000 R
C23 C 0.42186(9) 0.5560(2) 0.68486(12) 0.0451(5) Uani 1.000000 .
C24 C 0.41917(10) 0.4250(2) 0.70914(13) 0.0577(6) Uani 1.000000 .
H24 H 0.41412(10) 0.4052(2) 0.76249(13) 0.0693(7) Uiso 1.000000 R
C25 C 0.42392(10) 0.3229(2) 0.65480(13) 0.0566(6) Uani 1.000000 .
H25 H 0.42229(10) 0.2341(2) 0.67160(13) 0.0680(7) Uiso 1.000000 R
C26 C 0.41621(10) 0.6612(2) 0.74202(15) 0.0600(6) Uani 1.000000 .
N1 N 0.46317(8) 0.12022(16) 0.55660(10) 0.0488(4) Uani 1.000000 .
N3 N 0.37604(9) 0.21442(19) 0.45233(11) 0.0622(5) Uani 1.000000 .
H3 H 0.36435(9) 0.25397(19) 0.40299(11) 0.0746(6) Uiso 1.000000 R
N12 N 0.55876(9) 0.04199(18) 0.65103(11) 0.0591(5) Uani 1.000000 .
H12 H 0.54596(9) -0.03044(18) 0.66842(11) 0.0709(6) Uiso 1.000000 R
N19 N 0.55618(9) 0.23354(18) 0.57982(11) 0.0584(5) Uani 1.000000 .
N27 N 0.41096(11) 0.7416(2) 0.78846(14) 0.0891(7) Uani 1.000000 .
O28 O 0.45399(8) -0.07660(16) 0.62164(11) 0.0777(5) Uani 1.000000 .


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
C2 C20 1.522(3) . ?
C2 N1 1.476(2) . ?
C2 N3 1.427(3) . ?
C4 C5 1.388(3) . ?
C4 C9 1.387(3) . ?
C4 N3 1.385(3) . ?
C5 C6 1.367(4) . ?
C6 C7 1.378(4) . ?
C7 C8 1.361(4) . ?
C8 C9 1.387(3) . ?
C9 C10 1.463(3) . ?
C10 N1 1.378(3) . ?
C10 O28 1.227(3) . ?
C11 N1 1.391(3) . ?
C11 N12 1.342(3) . ?
C11 N19 1.306(3) . ?
C13 C14 1.379(3) . ?
C13 C18 1.387(3) . ?
C13 N12 1.374(3) . ?
C14 C15 1.361(4) . ?
C15 C16 1.377(4) . ?
C16 C17 1.363(4) . ?
C17 C18 1.374(3) . ?
C18 N19 1.390(3) . ?
C20 C21 1.379(3) . ?
C20 C25 1.380(3) . ?
C21 C22 1.361(3) . ?
C22 C23 1.383(3) . ?
C23 C24 1.370(3) . ?
C23 C26 1.432(3) . ?
C24 C25 1.373(3) . ?
C26 N27 1.132(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
N1 C2 C20 110.79(15) . . ?
N3 C2 C20 111.42(17) . . ?
N3 C2 N1 111.45(17) . . ?
C9 C4 C5 119.5(2) . . ?
N3 C4 C5 121.7(2) . . ?
N3 C4 C9 118.8(2) . . ?
C6 C5 C4 120.0(3) . . ?
C7 C6 C5 120.7(3) . . ?
C8 C7 C6 119.6(3) . . ?
C9 C8 C7 121.0(3) . . ?
C8 C9 C4 119.2(2) . . ?
C10 C9 C4 121.0(2) . . ?
C10 C9 C8 119.7(2) . . ?
N1 C10 C9 116.3(2) . . ?
O28 C10 C9 122.6(2) . . ?
O28 C10 N1 121.0(2) . . ?
N12 C11 N1 123.70(19) . . ?
N19 C11 N1 122.1(2) . . ?
N19 C11 N12 114.2(2) . . ?
C18 C13 C14 121.7(2) . . ?
N12 C13 C14 133.1(2) . . ?
N12 C13 C18 105.2(2) . . ?
C15 C14 C13 117.8(3) . . ?
C16 C15 C14 120.8(3) . . ?
C17 C16 C15 121.6(3) . . ?
C18 C17 C16 118.6(3) . . ?
C17 C18 C13 119.5(2) . . ?
N19 C18 C13 110.0(2) . . ?
N19 C18 C17 130.5(2) . . ?
C21 C20 C2 118.66(16) . . ?
C25 C20 C2 122.58(17) . . ?
C25 C20 C21 118.76(18) . . ?
C22 C21 C20 121.48(17) . . ?
C23 C22 C21 119.17(18) . . ?
C24 C23 C22 120.21(18) . . ?
C26 C23 C22 120.48(19) . . ?
C26 C23 C24 119.31(18) . . ?
C25 C24 C23 120.08(18) . . ?
C24 C25 C20 120.28(19) . . ?
N27 C26 C23 177.9(3) . . ?
C10 N1 C2 121.67(18) . . ?
C11 N1 C2 114.01(16) . . ?
C11 N1 C10 122.85(18) . . ?
C4 N3 C2 119.84(18) . . ?
C13 N12 C11 106.69(18) . . ?
C18 N19 C11 103.91(19) . . ?

####################################################################### 
# 
# 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_AP-BIN-5
_database_code_depnum_ccdc_archive 'CCDC 1524323'
_audit_update_record             
;
2016-12-23 deposited with the CCDC.
2017-06-12 downloaded from the CCDC.
;
_audit_creation_date             2015-08-06
_audit_creation_method           
;
  Olex2 1.2-ac2
  (compiled 2012.03.27 svn.r2268, GUI svn.r4156)
;
_chemical_formula_moiety         'C19 H16 N2 O2'
_chemical_formula_sum            'C19 H16 N2 O2'
_chemical_formula_weight         304.35
_chemical_oxdiff_formula         C19H16N2O2
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x+1/2,y+1/2,-z+1/2
3 -x,-y,-z
4 x-1/2,-y-1/2,z-1/2

_cell_length_a                   14.3966(17)
_cell_length_b                   6.8726(5)
_cell_length_c                   17.724(2)
_cell_angle_alpha                90
_cell_angle_beta                 113.844(15)
_cell_angle_gamma                90
_cell_volume                     1603.9(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4766
_cell_measurement_temperature    293.25(10)
_cell_measurement_theta_max      26.5110
_cell_measurement_theta_min      3.4500
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.93104
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_density_diffrn    1.2603
_exptl_crystal_F_000             640.2966
_exptl_crystal_size_max          0.82
_exptl_crystal_size_mid          0.82
_exptl_crystal_size_min          0.69
_diffrn_reflns_av_R_equivalents  0.0427
_diffrn_reflns_av_unetI/netI     0.0402
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            15027
_diffrn_reflns_theta_full        28.640762
_diffrn_reflns_theta_max         28.64
_diffrn_reflns_theta_min         3.09
_diffrn_ambient_temperature      293.25(10)
_diffrn_detector_area_resol_mean 8.0640
_diffrn_measured_fraction_theta_full 0.9972
_diffrn_measured_fraction_theta_max 0.9200
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -17.00   10.00   1.0000    5.0200
omega____ theta____ kappa____ phi______ frames
    -      -20.2184  -77.0000  -90.0000 27

#__ type_ start__ end____ width___ exp.time_
  2 omega  -30.00    8.00   1.0000    5.0200
omega____ theta____ kappa____ phi______ frames
    -      -20.2184   57.0000  -90.0000 38

#__ type_ start__ end____ width___ exp.time_
  3 omega  -88.00  -61.00   1.0000    5.0200
omega____ theta____ kappa____ phi______ frames
    -      -20.2184  -57.0000  150.0000 27

#__ type_ start__ end____ width___ exp.time_
  4 omega  -96.00  -70.00   1.0000    5.0200
omega____ theta____ kappa____ phi______ frames
    -      -20.2184  178.0000  -60.0000 26

#__ type_ start__ end____ width___ exp.time_
  5 omega  -94.00  -67.00   1.0000    5.0200
omega____ theta____ kappa____ phi______ frames
    -      -20.2184  178.0000   60.0000 27

#__ type_ start__ end____ width___ exp.time_
  6 omega  -24.00   25.00   1.0000    5.0200
omega____ theta____ kappa____ phi______ frames
    -      -20.2184  -99.0000  150.0000 49

#__ type_ start__ end____ width___ exp.time_
  7 omega  -46.00   46.00   1.0000    5.0200
omega____ theta____ kappa____ phi______ frames
    -       22.4059  -57.0000  150.0000 92

#__ type_ start__ end____ width___ exp.time_
  8 omega   28.00   62.00   1.0000    5.0200
omega____ theta____ kappa____ phi______ frames
    -       22.4059   57.0000  120.0000 34

#__ type_ start__ end____ width___ exp.time_
  9 omega  -50.00   50.00   1.0000    5.0200
omega____ theta____ kappa____ phi______ frames
    -       22.4059  -77.0000   30.0000 100

#__ type_ start__ end____ width___ exp.time_
 10 omega   -1.00   93.00   1.0000    5.0200
omega____ theta____ kappa____ phi______ frames
    -       22.4059   57.0000  -60.0000 94

#__ type_ start__ end____ width___ exp.time_
 11 omega   53.00   85.00   1.0000    5.0200
omega____ theta____ kappa____ phi______ frames
    -       22.4059   37.0000   90.0000 32
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0362033000
_diffrn_orient_matrix_UB_12      -0.0569950000
_diffrn_orient_matrix_UB_13      -0.0078316000
_diffrn_orient_matrix_UB_21      -0.0127166000
_diffrn_orient_matrix_UB_22      0.0486758000
_diffrn_orient_matrix_UB_23      -0.0381710000
_diffrn_orient_matrix_UB_31      0.0377912000
_diffrn_orient_matrix_UB_32      0.0710178000
_diffrn_orient_matrix_UB_33      0.0198952000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              11
_reflns_limit_h_min              -18
_reflns_limit_k_max              9
_reflns_limit_k_min              0
_reflns_limit_l_max              23
_reflns_limit_l_min              -10
_reflns_number_gt                2821
_reflns_number_total             3799
_reflns_odcompleteness_completeness 99.72
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
olex2.refine (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard,
H. Puschmann, in preparation, 2011)
;
_computing_structure_solution    'J. Appl. Cryst. (2007) 40, 786-790'
_refine_diff_density_max         0.476209
_refine_diff_density_min         -0.363763
_refine_diff_density_rms         0.077805
_refine_ls_d_res_high            0.741400
_refine_ls_d_res_low             6.583883
_refine_ls_goodness_of_fit_ref   1.074436
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    30
_refine_ls_number_parameters     208
_refine_ls_number_reflns         3799
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.101843
_refine_ls_R_factor_gt           0.071879
_refine_ls_restrained_S_all      1.074436
_refine_ls_shift/su_max          0.0082
_refine_ls_shift/su_mean         0.0002
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0464P)²+1.0418P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.156951
_atom_sites_solution_primary     iterative
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_refinement_flags_posn
O18 O 0.49250(12) 0.0047(2) 0.61346(10) 0.0501(4) Uani 1.000000 .
O23 O 0.24915(15) 0.6539(2) 0.53720(11) 0.0610(5) Uani 1.000000 .
N1 N 0.31551(13) 0.3850(2) 0.61512(10) 0.0348(4) Uani 1.000000 .
N9 N 0.26952(13) 0.0737(2) 0.55341(11) 0.0363(4) Uani 1.000000 .
H9 H 0.24905(13) -0.0359(2) 0.56455(11) 0.0436(5) Uiso 1.000000 R
C19 C 0.44649(16) 0.1821(3) 0.60348(12) 0.0371(5) Uani 1.000000 .
C10 C 0.34883(16) 0.1830(3) 0.61528(12) 0.0328(4) Uani 1.000000 .
H10 H 0.36180(16) 0.1257(3) 0.66926(12) 0.0393(5) Uiso 1.000000 R
C2 C 0.26633(16) 0.4780(3) 0.54162(13) 0.0389(5) Uani 1.000000 .
C11 C 0.35198(16) 0.4867(3) 0.69287(13) 0.0360(5) Uani 1.000000 .
C8 C 0.22785(15) 0.1522(3) 0.47562(13) 0.0336(5) Uani 1.000000 .
C3 C 0.23042(16) 0.3543(3) 0.46756(13) 0.0367(5) Uani 1.000000 .
C12 C 0.33597(17) 0.4064(3) 0.75812(14) 0.0440(5) Uani 1.000000 .
H12 H 0.30016(17) 0.2904(3) 0.75116(14) 0.0528(6) Uiso 1.000000 R
C16 C 0.40520(18) 0.6593(3) 0.70414(15) 0.0456(6) Uani 1.000000 .
H16 H 0.41764(18) 0.7131(3) 0.66098(15) 0.0547(7) Uiso 1.000000 R
C6 C 0.1400(2) 0.1242(4) 0.32928(16) 0.0587(7) Uani 1.000000 .
H6 H 0.1084(2) 0.0472(4) 0.28270(16) 0.0704(8) Uiso 1.000000 R
C15 C 0.43975(18) 0.7513(4) 0.77963(16) 0.0521(6) Uani 1.000000 .
H15 H 0.47384(18) 0.8692(4) 0.78617(16) 0.0626(8) Uiso 1.000000 R
C4 C 0.18942(19) 0.4366(4) 0.38920(15) 0.0538(7) Uani 1.000000 .
H4 H 0.19140(19) 0.5708(4) 0.38347(15) 0.0646(8) Uiso 1.000000 R
C13 C 0.37343(19) 0.4992(4) 0.83378(15) 0.0539(6) Uani 1.000000 .
H13 H 0.36351(19) 0.4430(4) 0.87767(15) 0.0646(8) Uiso 1.000000 R
C7 C 0.17946(17) 0.0388(3) 0.40532(15) 0.0447(6) Uani 1.000000 .
H7 H 0.17405(17) -0.0950(3) 0.41021(15) 0.0536(7) Uiso 1.000000 R
C14 C 0.42520(18) 0.6733(4) 0.84576(16) 0.0534(7) Uani 1.000000 .
C20 C 0.5016(2) 0.3139(4) 0.58438(17) 0.0580(7) Uani 1.000000 .
H20 H 0.4872(2) 0.4458(4) 0.57497(17) 0.0697(8) Uiso 1.000000 R
C21 C 0.5861(2) 0.2146(5) 0.58114(19) 0.0700(9) Uani 1.000000 .
H21 H 0.6374(2) 0.2684(5) 0.56857(19) 0.0840(10) Uiso 1.000000 R
C5 C 0.1461(2) 0.3224(4) 0.32025(16) 0.0634(8) Uani 1.000000 .
H5 H 0.1211(2) 0.3782(4) 0.26798(16) 0.0761(9) Uiso 1.000000 R
C17 C 0.4648(2) 0.7763(6) 0.92849(19) 0.0851(11) Uani 1.000000 .
H17a H 0.5373(3) 0.764(3) 0.9545(7) 0.1277(17) Uiso 1.000000 G
H17b H 0.4470(17) 0.9116(9) 0.9203(2) 0.1277(17) Uiso 1.000000 G
H17c H 0.4352(15) 0.719(2) 0.9629(6) 0.1277(17) Uiso 1.000000 G
C22 C 0.5779(2) 0.0302(5) 0.59949(17) 0.0639(8) Uani 1.000000 .
H22 H 0.6239(2) -0.0675(5) 0.60240(17) 0.0767(9) Uiso 1.000000 R


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O18 C19 1.365(3) .
O18 C22 1.360(3) .
O23 C2 1.230(2) .
N1 C10 1.469(2) .
N1 C2 1.364(3) .
N1 C11 1.441(3) .
N9 H9 0.8600 .
N9 C10 1.435(3) .
N9 C8 1.372(3) .
C19 C10 1.503(3) .
C19 C20 1.334(3) .
C10 H10 0.9800 .
C2 C3 1.471(3) .
C11 C12 1.382(3) .
C11 C16 1.382(3) .
C8 C3 1.398(3) .
C8 C7 1.394(3) .
C3 C4 1.391(3) .
C12 H12 0.9300 .
C12 C13 1.383(3) .
C16 H16 0.9300 .
C16 C15 1.378(3) .
C6 H6 0.9300 .
C6 C7 1.365(4) .
C6 C5 1.379(4) .
C15 H15 0.9300 .
C15 C14 1.380(4) .
C4 H4 0.9300 .
C4 C5 1.372(3) .
C13 H13 0.9300 .
C13 C14 1.380(4) .
C7 H7 0.9300 .
C14 C17 1.516(4) .
C20 H20 0.9300 .
C20 C21 1.416(4) .
C21 H21 0.9300 .
C21 C22 1.325(4) .
C5 H5 0.9300 .
C17 H17a 0.9600 .
C17 H17b 0.9600 .
C17 H17c 0.9600 .
C22 H22 0.9300 .

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C22 O18 C19 106.8(2) . .
C2 N1 C10 119.18(17) . .
C11 N1 C10 117.64(16) . .
C11 N1 C2 122.26(17) . .
C10 N9 H9 121.58(10) . .
C8 N9 H9 121.58(11) . .
C8 N9 C10 116.84(16) . .
C10 C19 O18 114.70(18) . .
C20 C19 O18 109.4(2) . .
C20 C19 C10 135.9(2) . .
N9 C10 N1 109.58(16) . .
C19 C10 N1 109.07(16) . .
C19 C10 N9 113.07(17) . .
H10 C10 N1 108.34(10) . .
H10 C10 N9 108.34(10) . .
H10 C10 C19 108.34(11) . .
N1 C2 O23 122.3(2) . .
C3 C2 O23 121.47(19) . .
C3 C2 N1 116.17(17) . .
C12 C11 N1 119.13(19) . .
C16 C11 N1 121.4(2) . .
C16 C11 C12 119.5(2) . .
C3 C8 N9 118.32(18) . .
C7 C8 N9 122.38(19) . .
C7 C8 C3 119.2(2) . .
C8 C3 C2 119.81(19) . .
C4 C3 C2 120.7(2) . .
C4 C3 C8 119.2(2) . .
H12 C12 C11 120.14(13) . .
C13 C12 C11 119.7(2) . .
C13 C12 H12 120.14(15) . .
H16 C16 C11 120.15(14) . .
C15 C16 C11 119.7(2) . .
C15 C16 H16 120.15(15) . .
C7 C6 H6 119.37(14) . .
C5 C6 H6 119.37(15) . .
C5 C6 C7 121.3(2) . .
H15 C15 C16 119.07(15) . .
C14 C15 C16 121.9(2) . .
C14 C15 H15 119.07(14) . .
H4 C4 C3 119.54(13) . .
C5 C4 C3 120.9(2) . .
C5 C4 H4 119.54(15) . .
H13 C13 C12 119.20(15) . .
C14 C13 C12 121.6(2) . .
C14 C13 H13 119.20(15) . .
C6 C7 C8 120.0(2) . .
H7 C7 C8 120.01(13) . .
H7 C7 C6 120.01(14) . .
C13 C14 C15 117.6(2) . .
C17 C14 C15 120.9(3) . .
C17 C14 C13 121.5(3) . .
H20 C20 C19 126.52(16) . .
C21 C20 C19 107.0(3) . .
C21 C20 H20 126.52(17) . .
H21 C21 C20 126.63(17) . .
C22 C21 C20 106.7(2) . .
C22 C21 H21 126.63(17) . .
C4 C5 C6 119.3(2) . .
H5 C5 C6 120.36(15) . .
H5 C5 C4 120.36(15) . .
H17a C17 C14 109.5 . .
H17b C17 C14 109.5 . .
H17b C17 H17a 109.5 . .
H17c C17 C14 109.5 . .
H17c C17 H17a 109.5 . .
H17c C17 H17b 109.5 . .
C21 C22 O18 110.1(3) . .
H22 C22 O18 124.93(16) . .
H22 C22 C21 124.93(17) . .
####################################################################### 
# 
# 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_BIN-2
_database_code_depnum_ccdc_archive 'CCDC 1063941'
_audit_update_record             
;
2015-05-08 deposited with the CCDC.
2017-06-12 downloaded from the CCDC.
;
_audit_creation_date             2015-04-07
_audit_creation_method           
;
  Olex2 1.2-ac2
  (compiled 2012.03.27 svn.r2268, GUI svn.r4156)
;
_chemical_formula_moiety         'C15 H14 N2 O'
_chemical_formula_sum            'C15 H14 N2 O'
_chemical_formula_weight         238.29
_chemical_oxdiff_formula         C15H14N2O
loop_
_atom_type_symbol
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
_atom_type_scat_dispersion_source
H 0.00000 0.00000 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
C 0.00347 0.00161 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
O 0.01158 0.00611 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'
N 0.00653 0.00323 'International Tables Volume C Table 6.1.1.4 (pp. 500-502)'
'Henke, Gullikson and Davis, At. Data and Nucl. Data Tables, 1993, 54, 2'

_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_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,y+1/2,-z+1/2
3 -x,-y,-z
4 x,-y-1/2,z-1/2

_cell_length_a                   13.027(2)
_cell_length_b                   8.8840(12)
_cell_length_c                   11.4246(17)
_cell_angle_alpha                90
_cell_angle_beta                 109.209(18)
_cell_angle_gamma                90
_cell_volume                     1248.5(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1471
_cell_measurement_temperature    289.84(17)
_cell_measurement_theta_max      28.2800
_cell_measurement_theta_min      4.0280
_exptl_absorpt_coefficient_mu    0.081
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85481
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            white
_exptl_crystal_density_diffrn    1.2676
_exptl_crystal_F_000             504.2104
_exptl_crystal_size_max          0.34
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.15
_diffrn_reflns_av_R_equivalents  0.0211
_diffrn_reflns_av_unetI/netI     0.0305
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5990
_diffrn_reflns_theta_full        28.773748
_diffrn_reflns_theta_max         28.77
_diffrn_reflns_theta_min         3.08
_diffrn_ambient_temperature      289.84(17)
_diffrn_detector_area_resol_mean 16.1279
_diffrn_measured_fraction_theta_full 0.9945
_diffrn_measured_fraction_theta_max 0.8853
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -22.00   22.00   1.0000    9.1400
omega____ theta____ kappa____ phi______ frames
    -      -20.3747  -99.0000 -180.0000 44

#__ type_ start__ end____ width___ exp.time_
  2 omega   48.00   74.00   1.0000    9.1400
omega____ theta____ kappa____ phi______ frames
    -       22.7184   37.0000   60.0000 26

#__ type_ start__ end____ width___ exp.time_
  3 omega  -10.00   35.00   1.0000    9.1400
omega____ theta____ kappa____ phi______ frames
    -       22.7184   37.0000   60.0000 45

#__ type_ start__ end____ width___ exp.time_
  4 omega   61.00   94.00   1.0000    9.1400
omega____ theta____ kappa____ phi______ frames
    -       22.7184  178.0000  -30.0000 33

#__ type_ start__ end____ width___ exp.time_
  5 omega   56.00   99.00   1.0000    9.1400
omega____ theta____ kappa____ phi______ frames
    -       22.7184  178.0000  150.0000 43

#__ type_ start__ end____ width___ exp.time_
  6 omega  -43.00   44.00   1.0000    9.1400
omega____ theta____ kappa____ phi______ frames
    -       22.7184    0.0000  -30.0000 87
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0110316000
_diffrn_orient_matrix_UB_12      -0.0761223000
_diffrn_orient_matrix_UB_13      0.0102661000
_diffrn_orient_matrix_UB_21      -0.0343517000
_diffrn_orient_matrix_UB_22      0.0239904000
_diffrn_orient_matrix_UB_23      0.0332897000
_diffrn_orient_matrix_UB_31      -0.0450289000
_diffrn_orient_matrix_UB_32      0.0004292000
_diffrn_orient_matrix_UB_33      -0.0557764000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_source                   'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              16
_reflns_limit_h_min              -17
_reflns_limit_k_max              12
_reflns_limit_k_min              0
_reflns_limit_l_max              15
_reflns_limit_l_min              0
_reflns_number_gt                2066
_reflns_number_total             2884
_reflns_odcompleteness_completeness 99.45
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
(compiled Aug  2 2013,16:46:58)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
olex2.refine (L.J. Bourhis, O.V. Dolomanov, R.J. Gildea, J.A.K. Howard,
H. Puschmann, in preparation, 2011)
;
_computing_structure_solution    'J. Appl. Cryst. (2007) 40, 786-790'
_refine_diff_density_max         0.515172
_refine_diff_density_min         -0.494768
_refine_diff_density_rms         0.053342
_refine_ls_d_res_high            0.738264
_refine_ls_d_res_low             6.606470
_refine_ls_goodness_of_fit_ref   1.062183
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    26
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2884
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.075829
_refine_ls_R_factor_gt           0.052442
_refine_ls_restrained_S_all      1.062183
_refine_ls_shift/su_max          0.0507
_refine_ls_shift/su_mean         0.0010
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0642P)²+0.3876P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.153069
_atom_sites_solution_primary     iterative
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_refinement_flags_posn
O18 O 0.86661(11) 0.45950(15) 0.37146(11) 0.0475(4) Uani 1.000000 .
N2 N 0.94182(12) 0.34218(17) 0.55489(13) 0.0407(4) Uani 1.000000 .
N10 N 0.86023(12) 0.13012(18) 0.61129(14) 0.0439(4) Uani 1.000000 .
C3 C 0.85919(14) 0.36737(19) 0.44960(15) 0.0379(4) Uani 1.000000 .
C11 C 1.04575(13) 0.20207(19) 0.73606(15) 0.0355(4) Uani 1.000000 .
C9 C 0.76492(14) 0.1585(2) 0.51623(16) 0.0402(4) Uani 1.000000 .
C4 C 0.76161(14) 0.2749(2) 0.43251(16) 0.0388(4) Uani 1.000000 .
C15 C 1.21284(16) 0.0764(2) 0.75459(19) 0.0512(5) Uani 1.000000 .
C1 C 0.93359(13) 0.2551(2) 0.65943(15) 0.0379(4) Uani 1.000000 .
C12 C 1.08922(15) 0.2452(2) 0.85829(16) 0.0442(4) Uani 1.000000 .
C16 C 1.10803(15) 0.1157(2) 0.68525(17) 0.0437(4) Uani 1.000000 .
C14 C 1.25775(15) 0.1209(2) 0.87756(19) 0.0503(5) Uani 1.000000 .
C13 C 1.19357(17) 0.2043(3) 0.92814(18) 0.0530(5) Uani 1.000000 .
C8 C 0.67224(15) 0.0689(3) 0.49679(19) 0.0522(5) Uani 1.000000 .
C7 C 0.58083(17) 0.0955(3) 0.3971(2) 0.0624(6) Uani 1.000000 .
C5 C 0.66775(16) 0.2983(3) 0.33158(19) 0.0543(5) Uani 1.000000 .
C6 C 0.57736(17) 0.2093(3) 0.3136(2) 0.0644(6) Uani 1.000000 .
C17 C 1.37303(18) 0.0790(4) 0.9520(3) 0.0817(9) Uani 1.000000 .
H5 H 0.66614(16) 0.3751(3) 0.27564(19) 0.0651(6) Uiso 1.000000 R
H6 H 0.51484(17) 0.2256(3) 0.2462(2) 0.0773(8) Uiso 1.000000 R
H7 H 0.51976(17) 0.0355(3) 0.3855(2) 0.0749(7) Uiso 1.000000 R
H8 H 0.67278(15) -0.0087(3) 0.55163(19) 0.0627(6) Uiso 1.000000 R
H16 H 1.07918(15) 0.0835(2) 0.60347(17) 0.0525(5) Uiso 1.000000 R
H15 H 1.25417(16) 0.0192(2) 0.71843(19) 0.0615(6) Uiso 1.000000 R
H13 H 1.22110(17) 0.2335(3) 1.01080(18) 0.0636(6) Uiso 1.000000 R
H12 H 1.04775(15) 0.3026(2) 0.89413(16) 0.0530(5) Uiso 1.000000 R
H2 H 1.00409(12) 0.38021(17) 0.56102(13) 0.0488(4) Uiso 1.000000 R
H10 H 0.87577(12) 0.04096(18) 0.64119(14) 0.0527(5) Uiso 1.000000 R
H1 H 0.90400(13) 0.3191(2) 0.71055(15) 0.0455(5) Uiso 1.000000 R
H17a H 1.3885(6) -0.0204(10) 0.9293(14) 0.1226(13) Uiso 1.000000 G
H17b H 1.4223(2) 0.1496(14) 0.9353(15) 0.1226(13) Uiso 1.000000 G
H17c H 1.3816(5) 0.081(2) 1.0387(3) 0.1226(13) Uiso 1.000000 G


loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O18 C3 1.238(2) .
N2 C3 1.343(2) .
N2 C1 1.456(2) .
N2 H2 0.8600 .
N10 C9 1.378(2) .
N10 C1 1.450(2) .
N10 H10 0.8600 .
C3 C4 1.472(3) .
C11 C1 1.511(2) .
C11 C12 1.377(2) .
C11 C16 1.376(3) .
C9 C4 1.399(3) .
C9 C8 1.402(3) .
C4 C5 1.393(3) .
C15 C16 1.379(3) .
C15 C14 1.390(3) .
C15 H15 0.9300 .
C1 H1 0.9800 .
C12 C13 1.379(3) .
C12 H12 0.9300 .
C16 H16 0.9300 .
C14 C13 1.378(3) .
C14 C17 1.509(3) .
C13 H13 0.9300 .
C8 C7 1.370(3) .
C8 H8 0.9300 .
C7 C6 1.381(3) .
C7 H7 0.9300 .
C5 C6 1.376(3) .
C5 H5 0.9300 .
C6 H6 0.9300 .
C17 H17a 0.9600 .
C17 H17b 0.9600 .
C17 H17c 0.9600 .

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
C1 N2 C3 124.72(15) . .
H2 N2 C3 117.64(10) . .
H2 N2 C1 117.64(9) . .
C1 N10 C9 117.97(15) . .
H10 N10 C9 121.01(10) . .
H10 N10 C1 121.01(9) . .
N2 C3 O18 121.76(16) . .
C4 C3 O18 122.84(15) . .
C4 C3 N2 115.38(15) . .
C12 C11 C1 119.82(16) . .
C16 C11 C1 121.44(15) . .
C16 C11 C12 118.69(16) . .
C4 C9 N10 119.44(16) . .
C8 C9 N10 121.79(17) . .
C8 C9 C4 118.69(17) . .
C9 C4 C3 119.39(15) . .
C5 C4 C3 120.72(17) . .
C5 C4 C9 119.85(18) . .
C14 C15 C16 121.12(19) . .
H15 C15 C16 119.44(12) . .
H15 C15 C14 119.44(12) . .
N10 C1 N2 108.23(13) . .
C11 C1 N2 108.84(13) . .
C11 C1 N10 111.82(14) . .
H1 C1 N2 109.30(9) . .
H1 C1 N10 109.30(9) . .
H1 C1 C11 109.30(9) . .
C13 C12 C11 120.75(18) . .
H12 C12 C11 119.63(11) . .
H12 C12 C13 119.63(12) . .
C15 C16 C11 120.55(17) . .
H16 C16 C11 119.72(10) . .
H16 C16 C15 119.72(12) . .
C13 C14 C15 117.70(18) . .
C17 C14 C15 120.6(2) . .
C17 C14 C13 121.7(2) . .
C14 C13 C12 121.15(18) . .
H13 C13 C12 119.42(12) . .
H13 C13 C14 119.42(11) . .
C7 C8 C9 120.1(2) . .
H8 C8 C9 119.94(12) . .
H8 C8 C7 119.94(14) . .
C6 C7 C8 121.5(2) . .
H7 C7 C8 119.27(14) . .
H7 C7 C6 119.27(12) . .
C6 C5 C4 120.8(2) . .
H5 C5 C4 119.59(12) . .
H5 C5 C6 119.59(13) . .
C5 C6 C7 119.1(2) . .
H6 C6 C7 120.47(12) . .
H6 C6 C5 120.47(13) . .
H17a C17 C14 109.5 . .
H17b C17 C14 109.5 . .
H17b C17 H17a 109.5 . .
H17c C17 C14 109.5 . .
H17c C17 H17a 109.5 . .
H17c C17 H17b 109.5 . .

