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

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

data_TP_Bn
_database_code_depnum_ccdc_archive 'CCDC 1572513'
_audit_update_record             
;
2017-09-04 deposited with the CCDC.
2017-10-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
1-benzyl-3-((2-(2-nitrobenzoyl)-1H-indol-3-yl)methyl)piperazine-2,5-dione
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C27 H22 N4 O5'
_chemical_formula_sum            'C27 H22 N4 O5'
_chemical_formula_weight         482.50

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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.
;

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

_cell_length_a                   13.2852(18)
_cell_length_b                   6.7684(10)
_cell_length_c                   14.0755(19)
_cell_angle_alpha                90
_cell_angle_beta                 112.709(4)
_cell_angle_gamma                90
_cell_volume                     1167.5(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2345
_cell_measurement_theta_min      2.69
_cell_measurement_theta_max      22.67

_exptl_crystal_description       Plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.372
_exptl_crystal_F_000             504
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.267
_exptl_crystal_size_mid          0.067
_exptl_crystal_size_min          0.026
_exptl_absorpt_coefficient_mu    0.097
_shelx_estimated_absorpt_T_min   0.975
_shelx_estimated_absorpt_T_max   0.997
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.8102
_exptl_absorpt_correction_T_max  0.9705
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   X-ray
_diffrn_measurement_device_type  'Bruker PHOTON100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11313
_diffrn_reflns_av_unetI/netI     0.0810
_diffrn_reflns_av_R_equivalents  0.0628
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.690
_diffrn_reflns_theta_max         25.350
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.974
_diffrn_measured_fraction_theta_full 0.974
_diffrn_reflns_Laue_measured_fraction_max 0.974
_diffrn_reflns_Laue_measured_fraction_full 0.974
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_point_group_measured_fraction_full 0.976
_reflns_number_total             4161
_reflns_number_gt                2428
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.836
_reflns_Friedel_fraction_max     0.978
_reflns_Friedel_fraction_full    0.979

_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.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0873P)²+0.0499P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.053(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 779 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   ?
_chemical_absolute_configuration None
_refine_ls_number_reflns         4161
_refine_ls_number_parameters     326
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1294
_refine_ls_R_factor_gt           0.0652
_refine_ls_wR_factor_ref         0.1898
_refine_ls_wR_factor_gt          0.1530
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_restrained_S_all      1.072
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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
O001 O 0.1720(4) 0.6624(9) 0.4419(3) 0.0770(17) Uani 1 1 d . . . . .
O002 O 0.2037(4) 0.9281(8) 0.8489(4) 0.0675(15) Uani 1 1 d . . . . .
N003 N 0.4244(5) 0.5487(11) 0.4028(5) 0.0650(17) Uani 1 1 d . . . . .
O1 O 0.4177(5) 0.6872(9) 0.4542(4) 0.0820(17) Uani 1 1 d . . . . .
O005 O 0.0643(5) 0.3281(9) 0.5800(4) 0.0811(18) Uani 1 1 d . . . . .
N006 N 0.1784(5) 0.5992(9) 0.8202(4) 0.0536(15) Uani 1 1 d . . . . .
N007 N 0.3959(4) 0.4322(9) 0.6474(4) 0.0572(16) Uani 1 1 d . . . . .
H007 H 0.4103 0.3272 0.6207 0.069 Uiso 1 1 calc R U . . .
N008 N 0.0771(4) 0.6593(10) 0.6112(4) 0.0570(16) Uani 1 1 d . . . . .
H008 H 0.0264 0.6842 0.5522 0.068 Uiso 1 1 calc R U . . .
C009 C 0.1747(6) 0.7862(12) 0.7882(5) 0.0516(18) Uani 1 1 d . . . . .
O00A O 0.4928(6) 0.5422(10) 0.3641(6) 0.114(3) Uani 1 1 d . . . . .
C00B C 0.3136(5) 0.5690(11) 0.5969(5) 0.0473(16) Uani 1 1 d . . . . .
C00C C 0.3149(6) 0.7175(10) 0.6653(5) 0.0515(18) Uani 1 1 d . . . . .
C00D C 0.1366(6) 0.8256(11) 0.6733(5) 0.0511(18) Uani 1 1 d . . . . .
H00D H 0.0869 0.9390 0.6570 0.061 Uiso 1 1 calc R U . . .
C00E C 0.1456(6) 0.5769(12) 0.9849(5) 0.0547(18) Uani 1 1 d . . . . .
C00F C 0.2706(6) 0.3837(11) 0.4266(5) 0.0503(18) Uani 1 1 d . . . . .
C00G C 0.3481(6) 0.3818(11) 0.3841(5) 0.0520(18) Uani 1 1 d . . . . .
C00H C 0.4500(6) 0.4953(11) 0.7479(5) 0.0542(19) Uani 1 1 d . . . . .
C00I C 0.0357(6) 0.5944(12) 0.9339(6) 0.0617(19) Uani 1 1 d . . . . .
H00I H 0.0062 0.6041 0.8625 0.074 Uiso 1 1 calc R U . . .
C00J C 0.4037(5) 0.6715(12) 0.7610(5) 0.0525(18) Uani 1 1 d . . . . .
C00K C 0.2355(6) 0.8830(11) 0.6469(5) 0.0558(19) Uani 1 1 d . . . . .
H00A H 0.2098 0.9222 0.5751 0.067 Uiso 1 1 calc R U . . .
H00B H 0.2722 0.9956 0.6885 0.067 Uiso 1 1 calc R U . . .
C00L C 0.2486(6) 0.5519(12) 0.4872(5) 0.0558(19) Uani 1 1 d . . . . .
C00M C 0.1996(7) 0.2236(12) 0.4050(6) 0.066(2) Uani 1 1 d . . . . .
H00M H 0.1469 0.2194 0.4333 0.079 Uiso 1 1 calc R U . . .
C00N C 0.1880(7) 0.5649(13) 1.0918(5) 0.071(2) Uani 1 1 d . . . . .
H00N H 0.2628 0.5500 1.1275 0.085 Uiso 1 1 calc R U . . .
C00O C 0.2245(6) 0.5564(14) 0.9313(5) 0.067(2) Uani 1 1 d . . . . .
H00C H 0.2856 0.6447 0.9643 0.081 Uiso 1 1 calc R U . . .
H00E H 0.2527 0.4226 0.9412 0.081 Uiso 1 1 calc R U . . .
C00P C 0.0962(6) 0.4721(14) 0.6399(6) 0.060(2) Uani 1 1 d . . . . .
C00Q C 0.4478(6) 0.7700(14) 0.8573(5) 0.069(2) Uani 1 1 d . . . . .
H00Q H 0.4174 0.8870 0.8686 0.082 Uiso 1 1 calc R U . . .
C00R C 0.3552(7) 0.2312(12) 0.3197(6) 0.069(2) Uani 1 1 d . . . . .
H00R H 0.4073 0.2348 0.2906 0.083 Uiso 1 1 calc R U . . .
C00S C 0.5416(6) 0.4110(15) 0.8262(6) 0.073(2) Uani 1 1 d . . . . .
H00S H 0.5732 0.2945 0.8162 0.087 Uiso 1 1 calc R U . . .
C00T C -0.0323(7) 0.5980(12) 0.9869(7) 0.076(2) Uani 1 1 d . . . . .
H00T H -0.1074 0.6070 0.9509 0.091 Uiso 1 1 calc R U . . .
C00U C 0.5369(7) 0.6866(18) 0.9333(6) 0.084(3) Uani 1 1 d . . . . .
H00U H 0.5681 0.7500 0.9966 0.101 Uiso 1 1 calc R U . . .
C00V C 0.2823(8) 0.0758(14) 0.3003(6) 0.080(2) Uani 1 1 d . . . . .
H00V H 0.2857 -0.0269 0.2578 0.096 Uiso 1 1 calc R U . . .
C00W C 0.2057(7) 0.0707(14) 0.3423(6) 0.078(2) Uani 1 1 d . . . . .
H00W H 0.1577 -0.0353 0.3290 0.094 Uiso 1 1 calc R U . . .
C00X C 0.1568(7) 0.4295(12) 0.7523(5) 0.065(2) Uani 1 1 d . . . . .
H00F H 0.1151 0.3342 0.7736 0.078 Uiso 1 1 calc R U . . .
H00G H 0.2259 0.3684 0.7613 0.078 Uiso 1 1 calc R U . . .
C00Y C 0.0106(9) 0.5884(13) 1.0943(7) 0.084(3) Uani 1 1 d . . . . .
H00Y H -0.0352 0.5913 1.1303 0.101 Uiso 1 1 calc R U . . .
C00Z C 0.5813(7) 0.5109(19) 0.9180(7) 0.089(3) Uani 1 1 d . . . . .
H00Z H 0.6405 0.4581 0.9722 0.106 Uiso 1 1 calc R U . . .
C010 C 0.1211(9) 0.5747(15) 1.1455(6) 0.084(3) Uani 1 1 d . . . . .
H010 H 0.1511 0.5720 1.2171 0.100 Uiso 1 1 calc R U . . .


_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
O001 C00L 1.225(8) . ?
O002 C009 1.244(9) . ?
N003 O1 1.209(8) . ?
N003 O00A 1.228(8) . ?
N003 C00G 1.472(9) . ?
O005 C00P 1.250(9) . ?
N006 C009 1.338(10) . ?
N006 C00X 1.450(10) . ?
N006 C00O 1.471(8) . ?
N007 C00H 1.384(8) . ?
N007 C00B 1.399(8) . ?
N007 H007 0.8600 . ?
N008 C00P 1.324(10) . ?
N008 C00D 1.457(9) . ?
N008 H008 0.8600 . ?
C009 C00D 1.520(9) . ?
C00B C00C 1.388(9) . ?
C00B C00L 1.453(9) . ?
C00C C00J 1.441(9) . ?
C00C C00K 1.491(10) . ?
C00D C00K 1.547(10) . ?
C00D H00D 0.9800 . ?
C00E C00I 1.361(10) . ?
C00E C00N 1.391(9) . ?
C00E C00O 1.516(10) . ?
C00F C00G 1.376(9) . ?
C00F C00M 1.391(10) . ?
C00F C00L 1.517(10) . ?
C00G C00R 1.392(10) . ?
C00H C00J 1.386(10) . ?
C00H C00S 1.409(10) . ?
C00I C00T 1.376(11) . ?
C00I H00I 0.9300 . ?
C00J C00Q 1.419(10) . ?
C00K H00A 0.9700 . ?
C00K H00B 0.9700 . ?
C00M C00W 1.382(11) . ?
C00M H00M 0.9300 . ?
C00N C010 1.373(11) . ?
C00N H00N 0.9300 . ?
C00O H00C 0.9700 . ?
C00O H00E 0.9700 . ?
C00P C00X 1.500(10) . ?
C00Q C00U 1.374(11) . ?
C00Q H00Q 0.9300 . ?
C00R C00V 1.383(12) . ?
C00R H00R 0.9300 . ?
C00S C00Z 1.370(13) . ?
C00S H00S 0.9300 . ?
C00T C00Y 1.396(11) . ?
C00T H00T 0.9300 . ?
C00U C00Z 1.381(13) . ?
C00U H00U 0.9300 . ?
C00V C00W 1.361(11) . ?
C00V H00V 0.9300 . ?
C00W H00W 0.9300 . ?
C00X H00F 0.9700 . ?
C00X H00G 0.9700 . ?
C00Y C010 1.366(13) . ?
C00Y H00Y 0.9300 . ?
C00Z H00Z 0.9300 . ?
C010 H010 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 N003 O00A 122.2(7) . . ?
O1 N003 C00G 119.8(6) . . ?
O00A N003 C00G 118.0(7) . . ?
C009 N006 C00X 123.7(5) . . ?
C009 N006 C00O 119.4(6) . . ?
C00X N006 C00O 116.1(6) . . ?
C00H N007 C00B 108.1(6) . . ?
C00H N007 H007 125.9 . . ?
C00B N007 H007 125.9 . . ?
C00P N008 C00D 124.1(6) . . ?
C00P N008 H008 117.9 . . ?
C00D N008 H008 117.9 . . ?
O002 C009 N006 122.5(6) . . ?
O002 C009 C00D 118.9(7) . . ?
N006 C009 C00D 118.6(7) . . ?
C00C C00B N007 109.2(5) . . ?
C00C C00B C00L 129.6(6) . . ?
N007 C00B C00L 121.0(6) . . ?
C00B C00C C00J 106.2(6) . . ?
C00B C00C C00K 127.2(6) . . ?
C00J C00C C00K 126.5(6) . . ?
N008 C00D C009 112.5(6) . . ?
N008 C00D C00K 111.4(5) . . ?
C009 C00D C00K 109.6(6) . . ?
N008 C00D H00D 107.7 . . ?
C009 C00D H00D 107.7 . . ?
C00K C00D H00D 107.7 . . ?
C00I C00E C00N 118.7(7) . . ?
C00I C00E C00O 123.5(6) . . ?
C00N C00E C00O 117.7(6) . . ?
C00G C00F C00M 117.1(7) . . ?
C00G C00F C00L 126.2(7) . . ?
C00M C00F C00L 116.5(6) . . ?
C00F C00G C00R 122.7(7) . . ?
C00F C00G N003 119.6(6) . . ?
C00R C00G N003 117.6(6) . . ?
N007 C00H C00J 108.6(6) . . ?
N007 C00H C00S 128.7(7) . . ?
C00J C00H C00S 122.6(7) . . ?
C00E C00I C00T 120.7(7) . . ?
C00E C00I H00I 119.6 . . ?
C00T C00I H00I 119.6 . . ?
C00H C00J C00Q 119.4(7) . . ?
C00H C00J C00C 107.9(6) . . ?
C00Q C00J C00C 132.7(8) . . ?
C00C C00K C00D 112.3(6) . . ?
C00C C00K H00A 109.2 . . ?
C00D C00K H00A 109.2 . . ?
C00C C00K H00B 109.2 . . ?
C00D C00K H00B 109.2 . . ?
H00A C00K H00B 107.9 . . ?
O001 C00L C00B 122.6(7) . . ?
O001 C00L C00F 117.8(6) . . ?
C00B C00L C00F 119.5(6) . . ?
C00W C00M C00F 121.4(8) . . ?
C00W C00M H00M 119.3 . . ?
C00F C00M H00M 119.3 . . ?
C010 C00N C00E 121.0(7) . . ?
C010 C00N H00N 119.5 . . ?
C00E C00N H00N 119.5 . . ?
N006 C00O C00E 115.3(6) . . ?
N006 C00O H00C 108.5 . . ?
C00E C00O H00C 108.5 . . ?
N006 C00O H00E 108.5 . . ?
C00E C00O H00E 108.5 . . ?
H00C C00O H00E 107.5 . . ?
O005 C00P N008 124.4(7) . . ?
O005 C00P C00X 117.7(8) . . ?
N008 C00P C00X 117.8(7) . . ?
C00U C00Q C00J 117.7(9) . . ?
C00U C00Q H00Q 121.2 . . ?
C00J C00Q H00Q 121.2 . . ?
C00V C00R C00G 117.8(8) . . ?
C00V C00R H00R 121.1 . . ?
C00G C00R H00R 121.1 . . ?
C00Z C00S C00H 116.1(9) . . ?
C00Z C00S H00S 122.0 . . ?
C00H C00S H00S 122.0 . . ?
C00I C00T C00Y 120.5(8) . . ?
C00I C00T H00T 119.8 . . ?
C00Y C00T H00T 119.8 . . ?
C00Z C00U C00Q 121.6(8) . . ?
C00Z C00U H00U 119.2 . . ?
C00Q C00U H00U 119.2 . . ?
C00W C00V C00R 121.2(8) . . ?
C00W C00V H00V 119.4 . . ?
C00R C00V H00V 119.4 . . ?
C00V C00W C00M 119.7(8) . . ?
C00V C00W H00W 120.1 . . ?
C00M C00W H00W 120.1 . . ?
N006 C00X C00P 115.6(7) . . ?
N006 C00X H00F 108.4 . . ?
C00P C00X H00F 108.4 . . ?
N006 C00X H00G 108.4 . . ?
C00P C00X H00G 108.4 . . ?
H00F C00X H00G 107.4 . . ?
C010 C00Y C00T 118.7(8) . . ?
C010 C00Y H00Y 120.6 . . ?
C00T C00Y H00Y 120.6 . . ?
C00U C00Z C00S 122.6(8) . . ?
C00U C00Z H00Z 118.7 . . ?
C00S C00Z H00Z 118.7 . . ?
C00N C010 C00Y 120.4(8) . . ?
C00N C010 H010 119.8 . . ?
C00Y C010 H010 119.8 . . ?

_refine_diff_density_max         0.577
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.060

####################################################################### 
# 
# 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_JCTP_NEW_a
_database_code_depnum_ccdc_archive 'CCDC 1572633'
_audit_update_record             
;
2017-09-05 deposited with the CCDC.
2017-10-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        
'methyl 1-(2-nitrophenyl)-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole-3-carboxylate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H17 N3 O4'
_chemical_formula_sum            'C19 H17 N3 O4'
_chemical_formula_weight         351.35

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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.
;

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'

_cell_length_a                   8.962(3)
_cell_length_b                   9.634(5)
_cell_length_c                   20.046(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1730.8(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    2082
_cell_measurement_theta_min      2.93
_cell_measurement_theta_max      25.42

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.348
_exptl_crystal_F_000             736
_exptl_transmission_factor_min   0.985
_exptl_transmission_factor_max   0.997
_exptl_crystal_size_max          0.156
_exptl_crystal_size_mid          0.066
_exptl_crystal_size_min          0.032
_exptl_absorpt_coefficient_mu    0.097
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   Multi-Scan
_exptl_absorpt_correction_T_min  0.8878
_exptl_absorpt_correction_T_max  0.9705
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      295(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   X-ray
_diffrn_measurement_device_type  'Bruker PHOTON100 CMOS'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            6840
_diffrn_reflns_av_unetI/netI     0.0534
_diffrn_reflns_av_R_equivalents  0.0383
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         2.345
_diffrn_reflns_theta_max         25.678
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measured_fraction_theta_full 0.980
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_Laue_measured_fraction_full 0.980
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_point_group_measured_fraction_full 0.970
_reflns_number_total             3183
_reflns_number_gt                2502
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.711
_reflns_Friedel_fraction_max     0.953
_reflns_Friedel_fraction_full    0.956

_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.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0539P)²+0.3532P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.025(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 819 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   ?
_chemical_absolute_configuration None
_refine_ls_number_reflns         3183
_refine_ls_number_parameters     237
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0689
_refine_ls_R_factor_gt           0.0483
_refine_ls_wR_factor_ref         0.1345
_refine_ls_wR_factor_gt          0.1121
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_restrained_S_all      1.092
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_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
O3 O 0.9702(3) 0.5631(4) 0.74442(19) 0.0699(10) Uani 1 1 d . . . . .
N1 N 0.2863(3) 0.6790(3) 0.76642(17) 0.0408(8) Uani 1 1 d . . . . .
H1 H 0.2199 0.6670 0.7360 0.049 Uiso 1 1 calc R U . . .
N2 N 0.6696(3) 0.5861(3) 0.71081(18) 0.0438(9) Uani 1 1 d . . . . .
H2 H 0.7330 0.6143 0.6816 0.053 Uiso 1 1 calc R U . . .
O1 O 0.2250(4) 0.4885(4) 0.6510(2) 0.0703(10) Uani 1 1 d . . . . .
O4 O 0.9091(3) 0.4188(4) 0.8260(2) 0.0782(12) Uani 1 1 d . . . . .
N3 N 0.2717(4) 0.5201(4) 0.5959(2) 0.0584(10) Uani 1 1 d . . . . .
C14 C 0.4732(4) 0.6747(4) 0.6390(2) 0.0391(9) Uani 1 1 d . . . . .
C3 C 0.3997(4) 0.7376(4) 0.8618(2) 0.0397(9) Uani 1 1 d . . . . .
C19 C 0.3694(4) 0.6426(5) 0.5900(2) 0.0480(10) Uani 1 1 d . . . . .
O2 O 0.2417(5) 0.4561(4) 0.5450(2) 0.0896(12) Uani 1 1 d . . . . .
C13 C 0.5072(4) 0.5853(4) 0.6994(2) 0.0377(9) Uani 1 1 d . . . . .
H13 H 0.4720 0.4902 0.6919 0.045 Uiso 1 1 calc R U . . .
C2 C 0.5081(4) 0.6786(4) 0.8177(2) 0.0401(9) Uani 1 1 d . . . . .
C11 C 0.8790(4) 0.5092(4) 0.7786(2) 0.0491(11) Uani 1 1 d . . . . .
C1 C 0.4357(4) 0.6451(4) 0.7608(2) 0.0375(9) Uani 1 1 d . . . . .
C8 C 0.2613(4) 0.7348(4) 0.8280(2) 0.0427(9) Uani 1 1 d . . . . .
C15 C 0.5519(4) 0.7976(4) 0.6300(2) 0.0445(10) Uani 1 1 d . . . . .
H15 H 0.6220 0.8239 0.6618 0.053 Uiso 1 1 calc R U . . .
C7 C 0.1298(4) 0.7829(4) 0.8569(2) 0.0504(11) Uani 1 1 d . . . . .
H7 H 0.0392 0.7798 0.8342 0.060 Uiso 1 1 calc R U . . .
C10 C 0.7122(4) 0.5349(4) 0.7759(2) 0.0429(10) Uani 1 1 d . . . . .
H10 H 0.6590 0.4481 0.7851 0.051 Uiso 1 1 calc R U . . .
C9 C 0.6699(4) 0.6432(5) 0.8283(2) 0.0472(10) Uani 1 1 d . . . . .
H9A H 0.6848 0.6061 0.8728 0.057 Uiso 1 1 calc R U . . .
H9B H 0.7313 0.7255 0.8233 0.057 Uiso 1 1 calc R U . . .
C6 C 0.1406(5) 0.8349(5) 0.9202(2) 0.0602(13) Uani 1 1 d . . . . .
H6 H 0.0548 0.8679 0.9409 0.072 Uiso 1 1 calc R U . . .
C4 C 0.4048(5) 0.7924(5) 0.9262(2) 0.0537(11) Uani 1 1 d . . . . .
H4 H 0.4944 0.7966 0.9496 0.064 Uiso 1 1 calc R U . . .
C5 C 0.2744(6) 0.8402(5) 0.9546(2) 0.0636(13) Uani 1 1 d . . . . .
H5 H 0.2763 0.8766 0.9976 0.076 Uiso 1 1 calc R U . . .
C16 C 0.5288(5) 0.8826(5) 0.5748(3) 0.0590(13) Uani 1 1 d . . . . .
H16 H 0.5814 0.9654 0.5706 0.071 Uiso 1 1 calc R U . . .
C18 C 0.3478(6) 0.7242(6) 0.5345(3) 0.0681(14) Uani 1 1 d . . . . .
H18 H 0.2787 0.6982 0.5023 0.082 Uiso 1 1 calc R U . . .
C17 C 0.4291(6) 0.8446(6) 0.5269(3) 0.0694(14) Uani 1 1 d . . . . .
H17 H 0.4159 0.8996 0.4893 0.083 Uiso 1 1 calc R U . . .
C12 C 1.0646(5) 0.3856(6) 0.8377(4) 0.094(2) Uani 1 1 d . . . . .
H12A H 1.1096 0.3554 0.7967 0.142 Uiso 1 1 calc R U . . .
H12B H 1.0716 0.3127 0.8702 0.142 Uiso 1 1 calc R U . . .
H12C H 1.1157 0.4664 0.8538 0.142 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O3 C11 1.186(5) . ?
N1 C8 1.365(5) . ?
N1 C1 1.383(5) . ?
N1 H1 0.8600 . ?
N2 C10 1.446(5) . ?
N2 C13 1.474(5) . ?
N2 H2 0.8600 . ?
O1 N3 1.219(5) . ?
O4 C11 1.318(6) . ?
O4 C12 1.449(5) . ?
N3 O2 1.222(5) . ?
N3 C19 1.475(6) . ?
C14 C19 1.387(6) . ?
C14 C15 1.390(5) . ?
C14 C13 1.516(5) . ?
C3 C4 1.396(6) . ?
C3 C8 1.413(6) . ?
C3 C2 1.433(5) . ?
C19 C18 1.376(7) . ?
C13 C1 1.503(5) . ?
C13 H13 0.9800 . ?
C2 C1 1.350(5) . ?
C2 C9 1.505(5) . ?
C11 C10 1.517(5) . ?
C8 C7 1.392(5) . ?
C15 C16 1.392(6) . ?
C15 H15 0.9300 . ?
C7 C6 1.368(6) . ?
C7 H7 0.9300 . ?
C10 C9 1.528(6) . ?
C10 H10 0.9800 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C6 C5 1.384(7) . ?
C6 H6 0.9300 . ?
C4 C5 1.379(6) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C16 C17 1.361(7) . ?
C16 H16 0.9300 . ?
C18 C17 1.378(8) . ?
C18 H18 0.9300 . ?
C17 H17 0.9300 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 N1 C1 109.0(3) . . ?
C8 N1 H1 125.5 . . ?
C1 N1 H1 125.5 . . ?
C10 N2 C13 113.5(3) . . ?
C10 N2 H2 123.2 . . ?
C13 N2 H2 123.2 . . ?
C11 O4 C12 117.3(4) . . ?
O1 N3 O2 123.7(4) . . ?
O1 N3 C19 118.5(4) . . ?
O2 N3 C19 117.8(4) . . ?
C19 C14 C15 115.9(4) . . ?
C19 C14 C13 124.9(4) . . ?
C15 C14 C13 119.1(4) . . ?
C4 C3 C8 118.7(4) . . ?
C4 C3 C2 134.4(4) . . ?
C8 C3 C2 106.9(4) . . ?
C18 C19 C14 122.6(4) . . ?
C18 C19 N3 116.0(4) . . ?
C14 C19 N3 121.3(4) . . ?
N2 C13 C1 106.9(3) . . ?
N2 C13 C14 108.6(3) . . ?
C1 C13 C14 110.5(3) . . ?
N2 C13 H13 110.2 . . ?
C1 C13 H13 110.2 . . ?
C14 C13 H13 110.2 . . ?
C1 C2 C3 106.9(3) . . ?
C1 C2 C9 121.9(4) . . ?
C3 C2 C9 131.0(4) . . ?
O3 C11 O4 124.4(4) . . ?
O3 C11 C10 126.0(4) . . ?
O4 C11 C10 109.6(4) . . ?
C2 C1 N1 109.9(3) . . ?
C2 C1 C13 125.3(3) . . ?
N1 C1 C13 124.7(3) . . ?
N1 C8 C7 130.2(4) . . ?
N1 C8 C3 107.3(3) . . ?
C7 C8 C3 122.5(4) . . ?
C14 C15 C16 122.0(4) . . ?
C14 C15 H15 119.0 . . ?
C16 C15 H15 119.0 . . ?
C6 C7 C8 116.6(4) . . ?
C6 C7 H7 121.7 . . ?
C8 C7 H7 121.7 . . ?
N2 C10 C11 110.3(4) . . ?
N2 C10 C9 108.8(3) . . ?
C11 C10 C9 109.4(3) . . ?
N2 C10 H10 109.5 . . ?
C11 C10 H10 109.5 . . ?
C9 C10 H10 109.5 . . ?
C2 C9 C10 107.2(3) . . ?
C2 C9 H9A 110.3 . . ?
C10 C9 H9A 110.3 . . ?
C2 C9 H9B 110.3 . . ?
C10 C9 H9B 110.3 . . ?
H9A C9 H9B 108.5 . . ?
C7 C6 C5 122.5(4) . . ?
C7 C6 H6 118.7 . . ?
C5 C6 H6 118.7 . . ?
C5 C4 C3 118.7(4) . . ?
C5 C4 H4 120.7 . . ?
C3 C4 H4 120.7 . . ?
C4 C5 C6 121.1(4) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C17 C16 C15 120.0(4) . . ?
C17 C16 H16 120.0 . . ?
C15 C16 H16 120.0 . . ?
C19 C18 C17 119.7(5) . . ?
C19 C18 H18 120.1 . . ?
C17 C18 H18 120.1 . . ?
C16 C17 C18 119.7(5) . . ?
C16 C17 H17 120.1 . . ?
C18 C17 H17 120.1 . . ?
O4 C12 H12A 109.5 . . ?
O4 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O4 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?

_refine_diff_density_max         0.218
_refine_diff_density_min         -0.284
_refine_diff_density_rms         0.038

