# Electronic Supplementary Material (ESI) for Green Chemistry.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_NGS-400B
_database_code_depnum_ccdc_archive 'CCDC 1443423'
_audit_update_record             
;
2015-12-21 deposited with the CCDC.
2016-04-29 downloaded from the CCDC.
;
_audit_creation_date             2015-10-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_chemical_formula_moiety         '2(C20 H20 N4 O2), H2 O'
_chemical_formula_sum            'C40 H42 N8 O5'
_chemical_formula_weight         714.83
_chemical_oxdiff_formula         C20H20O2N4
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      orthorhombic
_space_group_IT_number           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 2ab'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 x+1/2,-y+1/2,-z
3 -x,y,-z+1/2
4 -x+1/2,-y+1/2,z+1/2
5 -x,-y,-z
6 -x-1/2,y-1/2,z
7 x,-y,z-1/2
8 x-1/2,y-1/2,-z-1/2

_symmetry_Int_Tables_number      60
_cell_length_a                   15.4558(7)
_cell_length_b                   18.7716(10)
_cell_length_c                   26.3270(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     7638.3(6)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    5466
_cell_measurement_temperature    294.3(5)
_cell_measurement_theta_max      25.6020
_cell_measurement_theta_min      3.3580
_exptl_absorpt_coefficient_mu    0.084
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88571
_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            yellow
_exptl_crystal_density_diffrn    1.2431
_exptl_crystal_description       block
_exptl_crystal_F_000             3025.3494
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.23
_diffrn_reflns_av_R_equivalents  0.0520
_diffrn_reflns_av_unetI/netI     0.0629
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_l_max       35
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            36255
_diffrn_reflns_theta_full        26.3715
_diffrn_reflns_theta_max         26.37
_diffrn_reflns_theta_min         3.06
_diffrn_ambient_temperature      294.3(5)
_diffrn_detector_area_resol_mean 8.0640
_diffrn_measured_fraction_theta_full 0.9982
_diffrn_measured_fraction_theta_max 0.9982
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -90.00  -61.00   1.0000   20.0500
omega____ theta____ kappa____ phi______ frames
    -      -20.2184  -57.0000 -150.0000 29

#__ type_ start__ end____ width___ exp.time_
  2 omega   16.00   49.00   1.0000   20.0500
omega____ theta____ kappa____ phi______ frames
    -      -20.2184   57.0000 -120.0000 33

#__ type_ start__ end____ width___ exp.time_
  3 omega  -98.00  -54.00   1.0000   20.0500
omega____ theta____ kappa____ phi______ frames
    -      -20.2184  178.0000 -120.0000 44

#__ type_ start__ end____ width___ exp.time_
  4 omega  -38.00  -12.00   1.0000   20.0500
omega____ theta____ kappa____ phi______ frames
    -      -20.2184  -57.0000  150.0000 26

#__ type_ start__ end____ width___ exp.time_
  5 omega   35.00   97.00   1.0000   20.0500
omega____ theta____ kappa____ phi______ frames
    -       22.5622  178.0000  -90.0000 62

#__ type_ start__ end____ width___ exp.time_
  6 omega   60.00   86.00   1.0000   20.0500
omega____ theta____ kappa____ phi______ frames
    -       22.5622 -178.0000  -30.0000 26

#__ type_ start__ end____ width___ exp.time_
  7 omega   10.00   63.00   1.0000   20.0500
omega____ theta____ kappa____ phi______ frames
    -       22.5622  -99.0000   90.0000 53
;
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0067584000
_diffrn_orient_matrix_UB_12      0.0324755000
_diffrn_orient_matrix_UB_13      0.0131812000
_diffrn_orient_matrix_UB_21      -0.0364510000
_diffrn_orient_matrix_UB_22      -0.0150558000
_diffrn_orient_matrix_UB_23      0.0123550000
_diffrn_orient_matrix_UB_31      0.0270396000
_diffrn_orient_matrix_UB_32      -0.0121542000
_diffrn_orient_matrix_UB_33      0.0199756000
_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              19
_reflns_limit_h_min              0
_reflns_limit_k_max              23
_reflns_limit_k_min              0
_reflns_limit_l_max              32
_reflns_limit_l_min              0
_reflns_number_gt                4970
_reflns_number_total             7807
_reflns_odcompleteness_completeness 99.68
_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         0.3533
_refine_diff_density_min         -0.3279
_refine_diff_density_rms         0.0750
_refine_ls_d_res_high            0.8000
_refine_ls_d_res_low             6.6643
_refine_ls_goodness_of_fit_ref   1.0392
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    66
_refine_ls_number_parameters     489
_refine_ls_number_reflns         7807
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0955
_refine_ls_R_factor_gt           0.0561
_refine_ls_restrained_S_all      1.0392
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0427P)²+1.9166P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1147
_refine_ls_wR_factor_ref         0.1366
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2.a Free rotating group:
 O5(H5b,H5c)
2.b Secondary CH2 refined with riding coordinates:
 C15(H15a,H15b), C35(H35a,H35b), C11(H11a,H11b), C31(H31a,H31b)
2.c Aromatic/amide H refined with riding coordinates:
 N8(H8), N6(H6), N4(H4), N1(H1), N5(H5), C5(H5a), C22(H22), C3(H3), C4(H4a),
 C2(H2a), C25(H25), C23(H23), C24(H24)
2.d Idealised Me refined as rotating group:
 C20(H20a,H20b,H20c), C14(H14a,H14b,H14c), C40(H40a,H40b,H40c), C33(H33a,H33b,
 H33c), C13(H13a,H13b,H13c), C34(H34a,H34b,H34c)
;
_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
O3 O 0.73023(9) 0.37585(8) 0.37408(5) 0.0404(4) Uani 1.000000 .
O1 O 0.28399(10) 0.28898(9) 0.38546(6) 0.0459(4) Uani 1.000000 .
O4 O 0.72859(10) 0.23589(9) 0.46149(6) 0.0506(4) Uani 1.000000 .
O2 O 0.13849(10) 0.42577(10) 0.38165(6) 0.0585(5) Uani 1.000000 .
N7 N 0.61363(11) 0.25277(10) 0.23390(6) 0.0363(4) Uani 1.000000 .
N8 N 0.69685(12) 0.26048(10) 0.21826(6) 0.0383(4) Uani 1.000000 .
H8 H 0.71128(12) 0.26579(10) 0.18694(6) 0.0459(5) Uiso 1.000000 R
N6 N 0.55274(11) 0.23490(10) 0.31589(6) 0.0360(4) Uani 1.000000 .
H6 H 0.50089(11) 0.23309(10) 0.30412(6) 0.0432(5) Uiso 1.000000 R
N3 N 0.52679(11) 0.41289(10) 0.31668(7) 0.0375(4) Uani 1.000000 .
N4 N 0.55232(11) 0.40586(10) 0.36575(7) 0.0389(5) Uani 1.000000 .
H4 H 0.60551(11) 0.40093(10) 0.37466(7) 0.0467(5) Uiso 1.000000 R
N2 N 0.38764(11) 0.43096(10) 0.27990(7) 0.0372(5) Uani 1.000000 .
H2 H 0.4088(14) 0.4292(12) 0.2483(9) 0.0447(5) Uiso 1.000000 R
N1 N 0.27540(12) 0.35616(11) 0.45765(7) 0.0469(5) Uani 1.000000 .
H1 H 0.26642(12) 0.32240(11) 0.47910(7) 0.0563(6) Uiso 1.000000 R
N5 N 0.85455(11) 0.31111(11) 0.38080(7) 0.0463(5) Uani 1.000000 .
H5 H 0.88955(11) 0.34566(11) 0.38697(7) 0.0555(6) Uiso 1.000000 R
C17 C 0.44161(13) 0.41841(11) 0.32081(8) 0.0323(5) Uani 1.000000 .
C37 C 0.62162(13) 0.24676(11) 0.28386(7) 0.0307(5) Uani 1.000000 .
C38 C 0.70678(13) 0.25040(11) 0.30060(7) 0.0304(5) Uani 1.000000 .
C18 C 0.41209(13) 0.41474(11) 0.37059(8) 0.0318(5) Uani 1.000000 .
C16 C 0.30289(13) 0.44093(11) 0.28860(8) 0.0322(5) Uani 1.000000 .
C28 C 0.73079(12) 0.24649(11) 0.35618(7) 0.0300(5) Uani 1.000000 .
C27 C 0.76949(13) 0.31928(12) 0.37215(7) 0.0328(5) Uani 1.000000 .
C19 C 0.48619(13) 0.40734(11) 0.39924(8) 0.0354(5) Uani 1.000000 .
C39 C 0.75473(14) 0.25899(11) 0.25665(8) 0.0346(5) Uani 1.000000 .
C36 C 0.56758(13) 0.22619(11) 0.36587(7) 0.0322(5) Uani 1.000000 .
C8 C 0.28907(13) 0.34609(13) 0.40760(8) 0.0353(5) Uani 1.000000 .
C30 C 0.65820(14) 0.22438(12) 0.44098(8) 0.0368(5) Uani 1.000000 .
C29 C 0.64912(13) 0.22948(11) 0.38673(7) 0.0317(5) Uani 1.000000 .
C9 C 0.26602(13) 0.43506(11) 0.33582(8) 0.0327(5) Uani 1.000000 .
C7 C 0.31706(13) 0.41840(11) 0.38398(7) 0.0322(5) Uani 1.000000 .
C32 C 0.50288(15) 0.17463(13) 0.44646(9) 0.0476(6) Uani 1.000000 .
C10 C 0.17478(14) 0.44151(13) 0.34118(9) 0.0400(5) Uani 1.000000 .
C6 C 0.30011(13) 0.46876(13) 0.42795(8) 0.0403(6) Uani 1.000000 .
C15 C 0.24991(14) 0.45867(13) 0.24268(8) 0.0416(6) Uani 1.000000 .
H15a H 0.28599(14) 0.48350(13) 0.21828(8) 0.0500(7) Uiso 1.000000 R
H15b H 0.23019(14) 0.41483(13) 0.22698(8) 0.0500(7) Uiso 1.000000 R
C21 C 0.80836(14) 0.19768(13) 0.36524(8) 0.0391(5) Uani 1.000000 .
C12 C 0.17185(15) 0.50482(14) 0.25533(9) 0.0467(6) Uani 1.000000 .
C35 C 0.48808(14) 0.21559(12) 0.39724(8) 0.0414(6) Uani 1.000000 .
H35a H 0.46400(14) 0.26189(12) 0.40547(8) 0.0496(7) Uiso 1.000000 R
H35b H 0.44556(14) 0.19023(12) 0.37706(8) 0.0496(7) Uiso 1.000000 R
C11 C 0.12116(14) 0.46613(15) 0.29679(9) 0.0526(7) Uani 1.000000 .
H11a H 0.09294(14) 0.42502(15) 0.28183(9) 0.0631(8) Uiso 1.000000 R
H11b H 0.07624(14) 0.49769(15) 0.30927(9) 0.0631(8) Uiso 1.000000 R
C1 C 0.27766(14) 0.42833(15) 0.47024(8) 0.0463(6) Uani 1.000000 .
C31 C 0.58054(15) 0.20806(14) 0.47332(8) 0.0496(6) Uani 1.000000 .
H31a H 0.59858(15) 0.17615(14) 0.50030(8) 0.0595(8) Uiso 1.000000 R
H31b H 0.56158(15) 0.25203(14) 0.48916(8) 0.0595(8) Uiso 1.000000 R
C5 C 0.30430(15) 0.54139(14) 0.43066(11) 0.0548(7) Uani 1.000000 .
H5a H 0.31919(15) 0.56844(14) 0.40239(11) 0.0657(8) Uiso 1.000000 R
C20 C 0.50080(16) 0.40426(14) 0.45501(9) 0.0541(7) Uani 1.000000 .
H20a H 0.5611(2) 0.3964(9) 0.46165(9) 0.0811(10) Uiso 1.000000 GR
H20b H 0.4831(10) 0.4485(3) 0.47016(12) 0.0811(10) Uiso 1.000000 GR
H20c H 0.4676(8) 0.3659(6) 0.46925(12) 0.0811(10) Uiso 1.000000 GR
C14 C 0.11571(17) 0.51313(18) 0.20792(10) 0.0764(10) Uani 1.000000 .
H14a H 0.1495(4) 0.5337(11) 0.1811(3) 0.1146(15) Uiso 1.000000 GR
H14b H 0.0948(11) 0.4673(2) 0.1975(5) 0.1146(15) Uiso 1.000000 GR
H14c H 0.0676(8) 0.5437(9) 0.2154(3) 0.1146(15) Uiso 1.000000 GR
C26 C 0.87924(15) 0.23933(14) 0.37852(9) 0.0489(6) Uani 1.000000 .
C40 C 0.84955(15) 0.26338(15) 0.24682(10) 0.0559(7) Uani 1.000000 .
H40a H 0.8761(2) 0.2185(3) 0.2548(6) 0.0839(10) Uiso 1.000000 GR
H40b H 0.85928(16) 0.2744(9) 0.21166(17) 0.0839(10) Uiso 1.000000 GR
H40c H 0.8744(2) 0.3001(6) 0.2676(5) 0.0839(10) Uiso 1.000000 GR
C22 C 0.81740(19) 0.12593(14) 0.36054(10) 0.0587(7) Uani 1.000000 .
H22 H 0.77060(19) 0.09757(14) 0.35137(10) 0.0705(9) Uiso 1.000000 R
C3 C 0.2637(2) 0.5336(2) 0.51843(13) 0.0842(11) Uani 1.000000 .
H3 H 0.2512(2) 0.5562(2) 0.54898(13) 0.1010(13) Uiso 1.000000 R
C4 C 0.28558(18) 0.57381(19) 0.47714(14) 0.0762(10) Uani 1.000000 .
H4a H 0.28801(18) 0.62315(19) 0.47999(14) 0.0915(12) Uiso 1.000000 R
C2 C 0.25969(18) 0.4600(2) 0.51601(10) 0.0703(9) Uani 1.000000 .
H2a H 0.24530(18) 0.4330(2) 0.54440(10) 0.0843(11) Uiso 1.000000 R
C33 C 0.5213(2) 0.09641(14) 0.43449(11) 0.0717(9) Uani 1.000000 .
H33a H 0.4713(5) 0.0753(3) 0.4190(7) 0.1075(13) Uiso 1.000000 GR
H33b H 0.5695(8) 0.09326(15) 0.4116(6) 0.1075(13) Uiso 1.000000 GR
H33c H 0.5348(13) 0.0715(3) 0.46535(15) 0.1075(13) Uiso 1.000000 GR
C13 C 0.2000(2) 0.57815(15) 0.27409(12) 0.0709(8) Uani 1.000000 .
H13a H 0.2344(11) 0.57293(16) 0.3042(5) 0.1064(13) Uiso 1.000000 GR
H13b H 0.2336(11) 0.6013(5) 0.2482(3) 0.1064(13) Uiso 1.000000 GR
H13c H 0.1498(2) 0.6064(4) 0.2816(7) 0.1064(13) Uiso 1.000000 GR
C34 C 0.42188(18) 0.18088(18) 0.47977(10) 0.0740(9) Uani 1.000000 .
H34a H 0.4121(8) 0.2300(2) 0.4882(6) 0.1110(14) Uiso 1.000000 GR
H34b H 0.3728(3) 0.1626(10) 0.4616(3) 0.1110(14) Uiso 1.000000 GR
H34c H 0.4300(6) 0.1539(9) 0.5104(4) 0.1110(14) Uiso 1.000000 GR
C25 C 0.95926(19) 0.21043(19) 0.38737(12) 0.0797(10) Uani 1.000000 .
H25 H 1.00631(19) 0.23878(19) 0.39611(12) 0.0956(12) Uiso 1.000000 R
C23 C 0.8985(2) 0.09574(19) 0.36977(14) 0.0896(11) Uani 1.000000 .
H23 H 0.9058(2) 0.04671(19) 0.36704(14) 0.1075(13) Uiso 1.000000 R
C24 C 0.9671(2) 0.1376(2) 0.38276(15) 0.1049(13) Uani 1.000000 .
H24 H 1.0205(2) 0.1165(2) 0.38867(15) 0.1259(16) Uiso 1.000000 R
O5 O 0.97032(12) 0.42041(12) 0.40619(10) 0.0810(6) Uani 1.000000 .
H5b H 0.9616(18) 0.4612(9) 0.4193(13) 0.1215(10) Uiso 1.000000 G
H5c H 1.0233(6) 0.4166(16) 0.3979(13) 0.1215(10) 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
_geom_bond_publ_flag
O3 C27 1.224(2) . ?
O1 C8 1.223(3) . ?
O4 C30 1.234(2) . ?
O2 C10 1.240(2) . ?
N7 N8 1.358(2) . ?
N7 C37 1.326(2) . ?
N8 C39 1.350(3) . ?
N6 C37 1.376(2) . ?
N6 C36 1.346(2) . ?
N3 N4 1.357(2) . ?
N3 C17 1.325(2) . ?
N4 C19 1.350(3) . ?
N2 C17 1.383(3) . ?
N2 C16 1.343(3) . ?
N1 C8 1.348(3) . ?
N1 C1 1.395(3) . ?
N5 C27 1.343(3) . ?
N5 C26 1.402(3) . ?
C17 C18 1.389(3) . ?
C37 C38 1.390(3) . ?
C38 C28 1.511(3) . ?
C38 C39 1.383(3) . ?
C18 C19 1.378(3) . ?
C18 C7 1.512(3) . ?
C16 C9 1.372(3) . ?
C16 C15 1.498(3) . ?
C28 C27 1.550(3) . ?
C28 C29 1.530(3) . ?
C28 C21 1.528(3) . ?
C19 C20 1.487(3) . ?
C39 C40 1.490(3) . ?
C36 C29 1.376(3) . ?
C36 C35 1.494(3) . ?
C8 C7 1.554(3) . ?
C30 C29 1.438(3) . ?
C30 C31 1.503(3) . ?
C9 C7 1.526(3) . ?
C9 C10 1.422(3) . ?
C7 C6 1.517(3) . ?
C32 C35 1.524(3) . ?
C32 C31 1.528(3) . ?
C32 C33 1.529(4) . ?
C32 C34 1.533(3) . ?
C10 C11 1.505(3) . ?
C6 C1 1.391(3) . ?
C6 C5 1.367(3) . ?
C15 C12 1.522(3) . ?
C21 C26 1.390(3) . ?
C21 C22 1.360(3) . ?
C12 C11 1.527(3) . ?
C12 C14 1.528(3) . ?
C12 C13 1.526(4) . ?
C1 C2 1.372(3) . ?
C5 C4 1.397(4) . ?
C26 C25 1.371(3) . ?
C22 C23 1.397(4) . ?
C3 C4 1.366(5) . ?
C3 C2 1.384(5) . ?
C25 C24 1.377(5) . ?
C23 C24 1.363(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
C37 N7 N8 102.79(16) . . ?
C39 N8 N7 113.48(17) . . ?
C36 N6 C37 119.15(17) . . ?
C17 N3 N4 102.61(16) . . ?
C19 N4 N3 113.55(17) . . ?
C16 N2 C17 118.65(17) . . ?
C1 N1 C8 111.37(19) . . ?
C26 N5 C27 111.65(19) . . ?
N2 C17 N3 123.29(18) . . ?
C18 C17 N3 113.57(18) . . ?
C18 C17 N2 123.03(18) . . ?
N6 C37 N7 123.34(18) . . ?
C38 C37 N7 113.49(18) . . ?
C38 C37 N6 123.12(18) . . ?
C28 C38 C37 122.48(18) . . ?
C39 C38 C37 104.36(17) . . ?
C39 C38 C28 133.14(19) . . ?
C19 C18 C17 104.38(18) . . ?
C7 C18 C17 122.46(18) . . ?
C7 C18 C19 133.16(19) . . ?
C9 C16 N2 123.26(19) . . ?
C15 C16 N2 115.25(17) . . ?
C15 C16 C9 121.49(18) . . ?
C27 C28 C38 108.33(16) . . ?
C29 C28 C38 108.45(16) . . ?
C29 C28 C27 111.08(16) . . ?
C21 C28 C38 111.91(16) . . ?
C21 C28 C27 100.58(16) . . ?
C21 C28 C29 116.11(17) . . ?
N5 C27 O3 125.2(2) . . ?
C28 C27 O3 125.80(17) . . ?
C28 C27 N5 108.85(18) . . ?
C18 C19 N4 105.89(18) . . ?
C20 C19 N4 121.95(19) . . ?
C20 C19 C18 132.1(2) . . ?
C38 C39 N8 105.87(18) . . ?
C40 C39 N8 121.36(19) . . ?
C40 C39 C38 132.73(19) . . ?
C29 C36 N6 122.73(19) . . ?
C35 C36 N6 114.62(18) . . ?
C35 C36 C29 122.60(19) . . ?
N1 C8 O1 125.4(2) . . ?
C7 C8 O1 126.36(18) . . ?
C7 C8 N1 108.20(19) . . ?
C29 C30 O4 120.6(2) . . ?
C31 C30 O4 119.47(19) . . ?
C31 C30 C29 119.88(19) . . ?
C36 C29 C28 123.72(18) . . ?
C30 C29 C28 117.08(17) . . ?
C30 C29 C36 118.85(19) . . ?
C7 C9 C16 123.69(18) . . ?
C10 C9 C16 119.65(19) . . ?
C10 C9 C7 116.60(17) . . ?
C8 C7 C18 108.90(16) . . ?
C9 C7 C18 108.53(16) . . ?
C9 C7 C8 111.56(17) . . ?
C6 C7 C18 111.96(17) . . ?
C6 C7 C8 101.00(17) . . ?
C6 C7 C9 114.65(17) . . ?
C31 C32 C35 107.71(19) . . ?
C33 C32 C35 109.7(2) . . ?
C33 C32 C31 110.1(2) . . ?
C34 C32 C35 109.0(2) . . ?
C34 C32 C31 110.2(2) . . ?
C34 C32 C33 110.1(2) . . ?
C9 C10 O2 120.9(2) . . ?
C11 C10 O2 119.42(19) . . ?
C11 C10 C9 119.67(19) . . ?
C1 C6 C7 108.3(2) . . ?
C5 C6 C7 130.8(2) . . ?
C5 C6 C1 120.9(2) . . ?
C12 C15 C16 112.53(18) . . ?
C26 C21 C28 108.7(2) . . ?
C22 C21 C28 131.3(2) . . ?
C22 C21 C26 119.9(2) . . ?
C11 C12 C15 107.00(19) . . ?
C14 C12 C15 109.2(2) . . ?
C14 C12 C11 109.94(19) . . ?
C13 C12 C15 111.0(2) . . ?
C13 C12 C11 110.1(2) . . ?
C13 C12 C14 109.5(2) . . ?
C32 C35 C36 114.44(18) . . ?
C12 C11 C10 114.73(18) . . ?
C6 C1 N1 110.24(19) . . ?
C2 C1 N1 128.6(3) . . ?
C2 C1 C6 121.1(3) . . ?
C32 C31 C30 116.66(19) . . ?
C4 C5 C6 118.1(3) . . ?
C21 C26 N5 109.68(19) . . ?
C25 C26 N5 128.2(3) . . ?
C25 C26 C21 122.1(3) . . ?
C23 C22 C21 118.6(3) . . ?
C2 C3 C4 121.8(3) . . ?
C3 C4 C5 120.5(3) . . ?
C3 C2 C1 117.6(3) . . ?
C24 C25 C26 117.2(3) . . ?
C24 C23 C22 120.5(3) . . ?
C23 C24 C25 121.8(3) . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.000 0.133 0.250 116.1 1.6 ?
2 0.000 -0.133 0.750 116.1 1.6 ?
3 -0.008 0.333 0.180 10.7 0.1 ?
4 0.008 0.333 0.320 10.7 0.1 ?
5 -0.008 0.667 0.680 10.7 0.1 ?
6 0.008 0.667 0.820 10.7 0.1 ?
7 0.500 0.367 0.750 116.1 1.6 ?
8 0.500 0.633 0.250 116.1 1.6 ?
9 0.492 0.167 0.820 10.7 0.1 ?
10 0.492 0.833 0.320 10.7 0.1 ?
11 0.508 0.167 0.680 10.7 0.1 ?
12 0.508 0.833 0.180 10.7 0.1 ?

####################################################################### 
# 
# 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_NGS-3B
_database_code_depnum_ccdc_archive 'CCDC 1443510'
_audit_update_record             
;
2015-12-21 deposited with the CCDC.
2016-04-29 downloaded from the CCDC.
;
_audit_creation_date             2015-12-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.03.20 svn.r2914 for OlexSys, GUI svn.r4816)
;
_chemical_formula_moiety         '2(C20 H11 N3 O4)'
_chemical_formula_sum            'C40 H22 N6 O8'
_chemical_formula_weight         714.66
_chemical_oxdiff_formula         C20H11N3O4
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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 -x,-y,-z

_symmetry_Int_Tables_number      2
_cell_length_a                   10.3603(15)
_cell_length_b                   13.054(2)
_cell_length_c                   14.655(3)
_cell_angle_alpha                75.239(15)
_cell_angle_beta                 84.652(14)
_cell_angle_gamma                69.915(14)
_cell_volume                     1799.9(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1724
_cell_measurement_temperature    291.6(2)
_cell_measurement_theta_max      23.5480
_cell_measurement_theta_min      3.5750
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.71098
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.3185
_exptl_crystal_description       plate
_exptl_crystal_F_000             736.4006
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.09
_diffrn_reflns_av_R_equivalents  0.0675
_diffrn_reflns_av_unetI/netI     0.1308
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            12261
_diffrn_reflns_theta_full        29.0572
_diffrn_reflns_theta_max         29.06
_diffrn_reflns_theta_min         3.32
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      291.6(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0640
_diffrn_detector_type            Eos
_diffrn_measured_fraction_theta_full 0.9981
_diffrn_measured_fraction_theta_max 0.9981
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -6.00  90.00   1.00    7.56    --   19.62  37.00  30.00   96
  2  ω    -24.00  19.00   1.00    7.56    --  -17.43 -99.00-150.00   43
  3  ω    -24.00  22.00   1.00    7.56    --  -17.43 -99.00  30.00   46
  4  ω     35.00  95.00   1.00    7.56    --   19.62-178.00-120.00   60
  5  ω    -34.00  63.00   1.00    7.56    --   19.62 -19.00-180.00   97
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Eos, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0066617000
_diffrn_orient_matrix_UB_12      -0.0058535000
_diffrn_orient_matrix_UB_13      -0.0459763000
_diffrn_orient_matrix_UB_21      -0.0671020000
_diffrn_orient_matrix_UB_22      0.0400926000
_diffrn_orient_matrix_UB_23      -0.0031560000
_diffrn_orient_matrix_UB_31      0.0276951000
_diffrn_orient_matrix_UB_32      0.0436702000
_diffrn_orient_matrix_UB_33      -0.0195327000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              14
_reflns_limit_h_min              -14
_reflns_limit_k_max              17
_reflns_limit_k_min              -16
_reflns_limit_l_max              19
_reflns_limit_l_min              0
_reflns_number_gt                3683
_reflns_number_total             8117
_reflns_odcompleteness_completeness 99.27
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_threshold_expression     I>=2u(I)
_computing_cell_refinement       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.41 (Rigaku OD, 2015)'
_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    'olex2.solve (Bourhis et al., 2013)'
_refine_diff_density_max         0.7403
_refine_diff_density_min         -0.5885
_refine_diff_density_rms         0.1454
_refine_ls_d_res_high            0.7317
_refine_ls_d_res_low             6.1367
_refine_ls_goodness_of_fit_ref   0.9953
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    42
_refine_ls_number_parameters     488
_refine_ls_number_reflns         8117
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1796
_refine_ls_R_factor_gt           0.0942
_refine_ls_restrained_S_all      0.9953
_refine_ls_shift/su_max          0.0000
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1280P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2287
_refine_ls_wR_factor_ref         0.2954
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All N(H,H) groups
2.a Rotating group:
 N3(Ha,Hb), N6(H1a,H1b)
2.b Aromatic/amide H refined with riding coordinates:
 C23(H17), C24(H1ba), C25(H1o), C26(H1h), C36(H1s), C37(H1n), C38(H1u),
 C39(H1j), C6(H1g), C5(H1i), C4(H1l), C3(H15), C16(H1p), C17(H1q), C18(H1t),
 C19(H1c), N1(H4), N4(H5)
;
_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
O O 0.0810(3) 0.6202(2) 0.0278(2) 0.0488(8) Uani 1.000000 .
O1 O 0.1379(3) 0.6929(2) -0.2577(2) 0.0500(8) Uani 1.000000 .
O2 O -0.5869(3) 0.8056(2) -0.2619(2) 0.0491(8) Uani 1.000000 .
O3 O -0.4625(3) 0.8038(2) -0.5357(2) 0.0505(8) Uani 1.000000 .
O4 O -0.3005(3) 0.6416(2) -0.4920(2) 0.0642(9) Uani 1.000000 .
O5 O -0.0144(3) 0.7981(2) 0.0282(2) 0.0604(9) Uani 1.000000 .
O6 O -0.1753(3) 0.6436(2) -0.2733(2) 0.0573(8) Uani 1.000000 .
O7 O 0.1632(4) 0.9402(2) -0.1276(3) 0.0630(9) Uani 1.000000 .
N N -0.6067(4) 0.7329(3) -0.1097(3) 0.0559(10) Uani 1.000000 .
N1 N 0.1270(4) 0.7979(3) -0.4012(3) 0.0573(10) Uani 1.000000 .
C C -0.5417(4) 0.7983(3) -0.3517(3) 0.0397(10) Uani 1.000000 .
C1 C 0.1478(4) 0.5356(3) -0.0173(3) 0.0428(10) Uani 1.000000 .
C3 C -0.4545(4) 0.6136(3) -0.2058(3) 0.0411(10) Uani 1.000000 .
C4 C 0.0171(4) 0.8885(3) -0.2762(3) 0.0419(10) Uani 1.000000 .
C5 C 0.0434(4) 0.7579(3) -0.1205(3) 0.0403(10) Uani 1.000000 .
C6 C 0.1122(4) 0.6743(3) -0.1630(3) 0.0420(10) Uani 1.000000 .
C7 C 0.0327(4) 0.7297(3) -0.0183(3) 0.0444(10) Uani 1.000000 .
C8 C -0.0166(4) 0.8782(3) -0.1715(3) 0.0403(10) Uani 1.000000 .
N2 N -0.4062(4) 0.4336(3) -0.0747(3) 0.0592(11) Uani 1.000000 .
C9 C -0.3817(4) 0.6026(3) -0.2991(3) 0.0378(9) Uani 1.000000 .
C10 C -0.3957(4) 0.7126(3) -0.4676(3) 0.0445(10) Uani 1.000000 .
C11 C 0.1672(4) 0.5616(3) -0.1143(3) 0.0414(10) Uani 1.000000 .
C12 C 0.0883(4) 0.7989(3) -0.3116(3) 0.0431(10) Uani 1.000000 .
C13 C -0.5443(4) 0.7110(3) -0.1910(3) 0.0404(10) Uani 1.000000 .
C14 C -0.4454(4) 0.7077(3) -0.3708(3) 0.0414(10) Uani 1.000000 .
C15 C -0.6211(5) 0.9829(4) -0.5878(3) 0.0524(12) Uani 1.000000 .
N3 N -0.0684(4) 1.0747(3) -0.3953(3) 0.0647(12) Uani 1.000000 .
C16 C -0.4290(4) 0.5159(3) -0.1306(3) 0.0431(10) Uani 1.000000 .
C17 C 0.1942(5) 0.4298(4) 0.0357(3) 0.0520(12) Uani 1.000000 .
N4 N -0.1636(4) 0.4691(3) -0.2868(3) 0.0544(10) Uani 1.000000 .
N5 N -0.0636(4) 1.0396(3) -0.1129(3) 0.0582(11) Uani 1.000000 .
C18 C -0.2268(4) 0.5771(4) -0.2858(3) 0.0443(10) Uani 1.000000 .
C19 C -0.0309(4) 0.9913(3) -0.3398(3) 0.0456(11) Uani 1.000000 .
C1a C -0.1686(5) 0.9321(3) -0.1540(3) 0.0468(11) Uani 1.000000 .
C1b C 0.2654(5) 0.3450(4) -0.0065(4) 0.0624(14) Uani 1.000000 .
C1c C -0.4898(5) 0.4679(4) -0.3430(3) 0.0535(12) Uani 1.000000 .
C1d C -0.6067(4) 0.8970(3) -0.4219(3) 0.0408(10) Uani 1.000000 .
C1e C -0.5650(4) 0.8946(3) -0.5160(3) 0.0451(11) Uani 1.000000 .
C1f C -0.2517(5) 0.4185(3) -0.3079(3) 0.0516(12) Uani 1.000000 .
C1g C -0.7086(4) 0.9929(3) -0.4053(4) 0.0493(11) Uani 1.000000 .
C1h C 0.2384(5) 0.4744(3) -0.1566(4) 0.0559(12) Uani 1.000000 .
C1i C -0.7643(5) 1.0811(4) -0.4778(4) 0.0560(13) Uani 1.000000 .
C1j C -0.2778(5) 0.9020(4) -0.1686(3) 0.0540(12) Uani 1.000000 .
C1k C -0.3811(4) 0.4962(3) -0.3213(3) 0.0461(11) Uani 1.000000 .
C1l C -0.7220(5) 1.0763(4) -0.5700(4) 0.0536(12) Uani 1.000000 .
C1m C -0.1895(5) 1.0262(3) -0.1204(3) 0.0525(12) Uani 1.000000 .
C1n C -0.4269(6) 1.0591(5) -0.1127(4) 0.0800(18) Uani 1.000000 .
C1o C 0.2885(5) 0.3676(4) -0.1045(4) 0.0678(15) Uani 1.000000 .
C1p C -0.2251(6) 0.3091(4) -0.3159(4) 0.0678(15) Uani 1.000000 .
C1q C -0.3334(6) 0.2819(4) -0.3364(5) 0.0761(16) Uani 1.000000 .
C1r C 0.0421(5) 0.9541(3) -0.1345(3) 0.0495(11) Uani 1.000000 .
C1s C -0.3184(6) 1.0916(4) -0.0992(4) 0.0721(15) Uani 1.000000 .
C1t C -0.4622(6) 0.3590(4) -0.3512(4) 0.0650(14) Uani 1.000000 .
C1u C -0.4073(5) 0.9651(4) -0.1472(4) 0.0673(15) Uani 1.000000 .
H17 H 0.1779(5) 0.4148(4) 0.1004(3) 0.0624(14) Uiso 1.000000 R
H1ba H 0.2988(5) 0.2717(4) 0.0297(4) 0.0749(17) Uiso 1.000000 R
H1o H 0.3377(5) 0.3097(4) -0.1333(4) 0.0813(18) Uiso 1.000000 R
H1h H 0.2520(5) 0.4895(3) -0.2216(4) 0.0671(15) Uiso 1.000000 R
H1s H -0.3319(6) 1.1550(4) -0.0768(4) 0.0865(18) Uiso 1.000000 R
H1n H -0.5156(6) 1.1011(5) -0.0983(4) 0.096(2) Uiso 1.000000 R
H1u H -0.4823(5) 0.9449(4) -0.1557(4) 0.0808(18) Uiso 1.000000 R
H1j H -0.2642(5) 0.8397(4) -0.1928(3) 0.0649(14) Uiso 1.000000 R
H1g H -0.7383(4) 0.9963(3) -0.3440(4) 0.0592(14) Uiso 1.000000 R
H1i H -0.8313(5) 1.1452(4) -0.4660(4) 0.0672(15) Uiso 1.000000 R
H1l H -0.7623(5) 1.1366(4) -0.6197(4) 0.0643(15) Uiso 1.000000 R
H15 H -0.5915(5) 0.9807(4) -0.6494(3) 0.0629(14) Uiso 1.000000 R
H1p H -0.1371(6) 0.2565(4) -0.3077(4) 0.0813(18) Uiso 1.000000 R
H1q H -0.3189(6) 0.2088(4) -0.3402(5) 0.091(2) Uiso 1.000000 R
H1t H -0.5327(6) 0.3381(4) -0.3672(4) 0.0780(17) Uiso 1.000000 R
H1c H -0.5780(5) 0.5201(4) -0.3518(3) 0.0642(14) Uiso 1.000000 R
Ha H -0.6822(16) 0.7882(16) -0.1226(3) 0.0671(12) Uiso 1.000000 GR
Hb H -0.624(3) 0.6737(9) -0.0787(10) 0.0671(12) Uiso 1.000000 GR
H4 H -0.0774(4) 0.4346(3) -0.2757(3) 0.0652(12) Uiso 1.000000 R
H5 H -0.0544(4) 1.0955(3) -0.0965(3) 0.0699(13) Uiso 1.000000 R
H1a H 0.115(3) 0.7426(16) -0.4170(7) 0.0688(12) Uiso 1.000000 GR
H1b H 0.078(2) 0.8601(12) -0.4368(3) 0.0688(12) Uiso 1.000000 GR


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
O C1 1.378(5) . ?
O C7 1.352(5) . ?
O1 C6 1.364(5) . ?
O1 C12 1.354(5) . ?
O2 C 1.370(5) . ?
O2 C13 1.362(4) . ?
O3 C10 1.359(5) . ?
O3 C1e 1.367(5) . ?
O4 C10 1.198(5) . ?
O5 C7 1.204(5) . ?
O6 C18 1.220(5) . ?
O7 C1r 1.214(5) . ?
N C13 1.349(5) . ?
N1 C12 1.339(5) . ?
C C14 1.334(5) . ?
C C1d 1.424(5) . ?
C1 C11 1.387(6) . ?
C1 C17 1.344(5) . ?
C3 C9 1.514(6) . ?
C3 C13 1.350(5) . ?
C3 C16 1.420(6) . ?
C4 C8 1.523(6) . ?
C4 C12 1.350(6) . ?
C4 C19 1.382(5) . ?
C5 C6 1.348(6) . ?
C5 C7 1.452(6) . ?
C5 C8 1.492(5) . ?
C6 C11 1.401(5) . ?
C8 C1a 1.516(6) . ?
C8 C1r 1.548(6) . ?
N2 C16 1.138(5) . ?
C9 C14 1.482(5) . ?
C9 C18 1.543(6) . ?
C9 C1k 1.503(6) . ?
C10 C14 1.456(6) . ?
C11 C1h 1.386(6) . ?
C15 C1e 1.345(6) . ?
C15 C1l 1.372(6) . ?
N3 C19 1.147(5) . ?
C17 C1b 1.363(7) . ?
N4 C18 1.339(5) . ?
N4 C1f 1.391(5) . ?
N5 C1m 1.391(6) . ?
N5 C1r 1.350(6) . ?
C1a C1j 1.368(6) . ?
C1a C1m 1.380(6) . ?
C1b C1o 1.406(7) . ?
C1c C1k 1.384(6) . ?
C1c C1t 1.385(6) . ?
C1d C1e 1.412(6) . ?
C1d C1g 1.392(6) . ?
C1f C1k 1.371(6) . ?
C1f C1p 1.393(6) . ?
C1g C1i 1.349(6) . ?
C1h C1o 1.353(6) . ?
C1i C1l 1.391(7) . ?
C1j C1u 1.367(7) . ?
C1m C1s 1.372(7) . ?
C1n C1s 1.376(8) . ?
C1n C1u 1.389(8) . ?
C1p C1q 1.365(7) . ?
C1q C1t 1.364(7) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 O C1 122.9(3) . . ?
C12 O1 C6 118.7(3) . . ?
C13 O2 C 118.0(3) . . ?
C1e O3 C10 122.9(3) . . ?
C14 C O2 122.9(4) . . ?
C1d C O2 113.4(4) . . ?
C1d C C14 123.7(4) . . ?
C11 C1 O 119.7(3) . . ?
C17 C1 O 118.0(4) . . ?
C17 C1 C11 122.3(4) . . ?
C13 C3 C9 123.3(4) . . ?
C16 C3 C9 118.4(3) . . ?
C16 C3 C13 118.3(4) . . ?
C12 C4 C8 122.5(3) . . ?
C19 C4 C8 120.2(4) . . ?
C19 C4 C12 117.2(4) . . ?
C7 C5 C6 117.7(4) . . ?
C8 C5 C6 124.1(4) . . ?
C8 C5 C7 118.1(4) . . ?
C5 C6 O1 122.5(4) . . ?
C11 C6 O1 113.9(4) . . ?
C11 C6 C5 123.5(4) . . ?
O5 C7 O 117.9(4) . . ?
C5 C7 O 118.2(4) . . ?
C5 C7 O5 123.9(4) . . ?
C5 C8 C4 108.6(3) . . ?
C1a C8 C4 112.2(3) . . ?
C1a C8 C5 115.0(3) . . ?
C1r C8 C4 109.3(3) . . ?
C1r C8 C5 111.4(3) . . ?
C1r C8 C1a 100.1(3) . . ?
C14 C9 C3 108.2(3) . . ?
C18 C9 C3 108.6(3) . . ?
C18 C9 C14 113.2(3) . . ?
C1k C9 C3 109.5(3) . . ?
C1k C9 C14 115.9(3) . . ?
C1k C9 C18 101.2(3) . . ?
O4 C10 O3 117.3(4) . . ?
C14 C10 O3 118.0(4) . . ?
C14 C10 O4 124.8(4) . . ?
C6 C11 C1 117.7(4) . . ?
C1h C11 C1 117.9(4) . . ?
C1h C11 C6 124.4(4) . . ?
N1 C12 O1 108.6(4) . . ?
C4 C12 O1 123.4(4) . . ?
C4 C12 N1 127.9(4) . . ?
N C13 O2 109.2(3) . . ?
C3 C13 O2 122.2(4) . . ?
C3 C13 N 128.5(4) . . ?
C9 C14 C 124.2(4) . . ?
C10 C14 C 118.4(4) . . ?
C10 C14 C9 117.3(4) . . ?
C1l C15 C1e 119.8(5) . . ?
N2 C16 C3 175.5(5) . . ?
C1b C17 C1 119.3(5) . . ?
C1f N4 C18 113.0(4) . . ?
C1r N5 C1m 111.6(4) . . ?
C9 C18 O6 125.2(4) . . ?
N4 C18 O6 127.7(4) . . ?
N4 C18 C9 107.1(3) . . ?
N3 C19 C4 177.4(5) . . ?
C1j C1a C8 129.9(4) . . ?
C1m C1a C8 109.7(4) . . ?
C1m C1a C1j 120.4(4) . . ?
C1o C1b C17 120.4(4) . . ?
C1t C1c C1k 117.5(4) . . ?
C1e C1d C 116.1(4) . . ?
C1g C1d C 125.7(4) . . ?
C1g C1d C1e 118.2(4) . . ?
C15 C1e O3 118.6(4) . . ?
C1d C1e O3 120.4(4) . . ?
C1d C1e C15 121.0(4) . . ?
C1k C1f N4 108.7(4) . . ?
C1p C1f N4 130.1(4) . . ?
C1p C1f C1k 121.2(5) . . ?
C1i C1g C1d 120.4(5) . . ?
C1o C1h C11 120.9(5) . . ?
C1l C1i C1g 120.2(4) . . ?
C1u C1j C1a 118.9(5) . . ?
C1c C1k C9 129.5(4) . . ?
C1f C1k C9 109.4(4) . . ?
C1f C1k C1c 120.8(4) . . ?
C1i C1l C15 120.3(4) . . ?
C1a C1m N5 109.4(4) . . ?
C1s C1m N5 128.7(5) . . ?
C1s C1m C1a 121.8(5) . . ?
C1u C1n C1s 121.6(5) . . ?
C1h C1o C1b 119.3(5) . . ?
C1q C1p C1f 117.4(5) . . ?
C1t C1q C1p 121.9(5) . . ?
C8 C1r O7 125.6(4) . . ?
N5 C1r O7 125.7(4) . . ?
N5 C1r C8 108.7(4) . . ?
C1n C1s C1m 117.1(5) . . ?
C1q C1t C1c 121.2(5) . . ?
C1n C1u C1j 120.1(5) . . ?

_smtbx_masks_special_details     ?
loop_
_smtbx_masks_void_nr
_smtbx_masks_void_average_x
_smtbx_masks_void_average_y
_smtbx_masks_void_average_z
_smtbx_masks_void_volume
_smtbx_masks_void_count_electrons
_smtbx_masks_void_content
1 0.000 0.500 0.500 263.4 17.4 ?

_olex2_date_sample_data_collection 2015-12-11
_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 1.299
_oxdiff_exptl_absorpt_empirical_full_min 0.787
_chemical_name_systematic        
2'-amino-2,5'-dioxo-5'H-spiro[indoline-3,4'-pyrano[3,2-c]chromene]-3'-carbonitrile
_chemical_name_common            Spirooxindole
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Methanol'
