# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2018

####################################################################### 
# 
# 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. 
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data_d8v17444
_database_code_depnum_ccdc_archive 'CCDC 1860102'
_audit_update_record             
;
2018-08-03 deposited with the CCDC.
2018-09-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H22 N4 O4'
_chemical_formula_weight         430.45

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           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   18.2546(6)
_cell_length_b                   9.1982(3)
_cell_length_c                   13.3199(4)
_cell_angle_alpha                90
_cell_angle_beta                 108.2310(10)
_cell_angle_gamma                90
_cell_volume                     2124.27(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    8483
_cell_measurement_theta_min      0.6975
_cell_measurement_theta_max      0.7456

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.346
_exptl_crystal_F_000             904
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.094
_shelx_estimated_absorpt_T_min   0.985
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6975
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            31544
_diffrn_reflns_av_unetI/netI     0.0292
_diffrn_reflns_av_R_equivalents  0.0522
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.738
_diffrn_reflns_theta_max         25.495
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3944
_reflns_number_gt                2834
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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-2013 (Sheldrick, 2013)'
_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)+(0.0559P)²+0.8654P] 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
_refine_ls_extinction_coef       0.015(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3944
_refine_ls_number_parameters     292
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0736
_refine_ls_R_factor_gt           0.0494
_refine_ls_wR_factor_ref         0.1352
_refine_ls_wR_factor_gt          0.1184
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_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
N1 N 0.93957(10) 0.56237(19) 0.18419(14) 0.0480(4) Uani 1 1 d . . . . .
N2 N 0.97448(11) 0.6916(2) 0.19350(16) 0.0635(6) Uani 1 1 d . . . . .
N3 N 0.55082(11) 0.0043(2) 0.32649(15) 0.0578(5) Uani 1 1 d . . . . .
N4 N 0.49086(14) 0.0170(3) 0.3624(2) 0.0918(8) Uani 1 1 d . . . . .
O1 O 0.74904(9) 0.29916(18) 0.27840(11) 0.0596(5) Uani 1 1 d . . . . .
O2 O 0.84587(8) 0.37298(17) 0.58881(10) 0.0547(4) Uani 1 1 d . . . . .
O3 O 1.00364(10) 0.7169(2) 0.12283(15) 0.0775(6) Uani 1 1 d . . . . .
O4 O 0.43842(14) -0.0697(3) 0.32258(19) 0.1273(11) Uani 1 1 d . . . . .
C1 C 0.80787(11) 0.3992(2) 0.31185(15) 0.0433(5) Uani 1 1 d . . . . .
C2 C 0.84368(11) 0.4319(2) 0.23745(16) 0.0443(5) Uani 1 1 d . . . . .
H2A H 0.8271 0.3887 0.1710 0.053 Uiso 1 1 calc R U . . .
C3 C 0.90389(11) 0.5287(2) 0.26208(16) 0.0427(5) Uani 1 1 d . . . . .
C4 C 0.92889(13) 0.5907(2) 0.36218(17) 0.0529(6) Uani 1 1 d . . . . .
H4 H 0.9706 0.6542 0.3803 0.063 Uiso 1 1 calc R U . . .
C5 C 0.89164(13) 0.5575(2) 0.43388(17) 0.0529(6) Uani 1 1 d . . . . .
H5 H 0.9085 0.6006 0.5004 0.063 Uiso 1 1 calc R U . . .
C6 C 0.82923(12) 0.4614(2) 0.41096(15) 0.0435(5) Uani 1 1 d . . . . .
C7 C 0.78918(12) 0.4259(2) 0.49144(15) 0.0449(5) Uani 1 1 d . . . . .
C8 C 0.72856(11) 0.3100(2) 0.44900(14) 0.0418(5) Uani 1 1 d . . . . .
C9 C 0.71161(12) 0.2557(2) 0.34761(15) 0.0437(5) Uani 1 1 d . . . . .
C10 C 0.65458(12) 0.1539(2) 0.30796(16) 0.0478(5) Uani 1 1 d . . . . .
H10 H 0.6449 0.1186 0.2396 0.057 Uiso 1 1 calc R U . . .
C11 C 0.61214(12) 0.1046(2) 0.36969(16) 0.0459(5) Uani 1 1 d . . . . .
C12 C 0.62866(13) 0.1540(2) 0.47314(17) 0.0517(6) Uani 1 1 d . . . . .
H12 H 0.6014 0.1187 0.5165 0.062 Uiso 1 1 calc R U . . .
C13 C 0.68548(13) 0.2551(2) 0.51003(16) 0.0500(5) Uani 1 1 d . . . . .
H13 H 0.6958 0.2887 0.5789 0.060 Uiso 1 1 calc R U . . .
C14 C 0.75553(12) 0.5573(2) 0.52929(16) 0.0464(5) Uani 1 1 d . . . . .
C15 C 0.69501(15) 0.6457(3) 0.4707(2) 0.0639(6) Uani 1 1 d . . . . .
H15 H 0.6719 0.6310 0.3986 0.077 Uiso 1 1 calc R U . . .
C16 C 0.67062(17) 0.7553(3) 0.5229(3) 0.0798(8) Uani 1 1 d . . . . .
H16 H 0.6300 0.8150 0.4859 0.096 Uiso 1 1 calc R U . . .
C17 C 0.70625(18) 0.7776(3) 0.6306(3) 0.0796(8) Uani 1 1 d . . . . .
H17 H 0.6894 0.8529 0.6645 0.096 Uiso 1 1 calc R U . . .
C18 C 0.76538(16) 0.6911(3) 0.6873(2) 0.0684(7) Uani 1 1 d . . . . .
H18 H 0.7887 0.7062 0.7593 0.082 Uiso 1 1 calc R U . . .
C19 C 0.79018(13) 0.5795(2) 0.63493(17) 0.0524(6) Uani 1 1 d . . . . .
C20 C 0.85174(14) 0.4700(3) 0.67503(17) 0.0579(6) Uani 1 1 d . . . . .
H20A H 0.9020 0.5164 0.6977 0.069 Uiso 1 1 calc R U . . .
H20B H 0.8445 0.4177 0.7345 0.069 Uiso 1 1 calc R U . . .
C21 C 0.93516(14) 0.4660(3) 0.09538(19) 0.0617(7) Uani 1 1 d . . . . .
H21A H 0.9270 0.3672 0.1151 0.074 Uiso 1 1 calc R U . . .
H21B H 0.9840 0.4686 0.0810 0.074 Uiso 1 1 calc R U . . .
C22 C 0.87145(18) 0.5059(3) -0.0041(2) 0.0861(9) Uani 1 1 d . . . . .
H22A H 0.8232 0.5092 0.0105 0.129 Uiso 1 1 calc R U . . .
H22B H 0.8686 0.4344 -0.0577 0.129 Uiso 1 1 calc R U . . .
H22C H 0.8820 0.5994 -0.0284 0.129 Uiso 1 1 calc R U . . .
C23 C 0.55296(16) -0.1045(3) 0.2463(2) 0.0720(7) Uani 1 1 d . . . . .
H23A H 0.5305 -0.1945 0.2610 0.086 Uiso 1 1 calc R U . . .
H23B H 0.6063 -0.1239 0.2517 0.086 Uiso 1 1 calc R U . . .
C24 C 0.51090(19) -0.0578(4) 0.1367(2) 0.0990(11) Uani 1 1 d . . . . .
H24A H 0.4574 -0.0439 0.1295 0.148 Uiso 1 1 calc R U . . .
H24B H 0.5158 -0.1310 0.0879 0.148 Uiso 1 1 calc R U . . .
H24C H 0.5323 0.0320 0.1218 0.148 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
N1 N2 1.336(2) . ?
N1 C3 1.421(3) . ?
N1 C21 1.460(3) . ?
N2 O3 1.240(2) . ?
N3 N4 1.330(3) . ?
N3 C11 1.426(3) . ?
N3 C23 1.473(3) . ?
N4 O4 1.232(3) . ?
O1 C9 1.367(2) . ?
O1 C1 1.378(2) . ?
O2 C20 1.432(3) . ?
O2 C7 1.466(2) . ?
C1 C6 1.378(3) . ?
C1 C2 1.380(3) . ?
C2 C3 1.372(3) . ?
C2 H2A 0.9300 . ?
C3 C4 1.389(3) . ?
C4 C5 1.369(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.399(3) . ?
C5 H5 0.9300 . ?
C6 C7 1.510(3) . ?
C7 C14 1.512(3) . ?
C7 C8 1.513(3) . ?
C8 C9 1.381(3) . ?
C8 C13 1.391(3) . ?
C9 C10 1.377(3) . ?
C10 C11 1.371(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.391(3) . ?
C12 C13 1.365(3) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 C19 1.366(3) . ?
C14 C15 1.397(3) . ?
C15 C16 1.375(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.394(4) . ?
C16 H16 0.9300 . ?
C17 C18 1.363(4) . ?
C17 H17 0.9300 . ?
C18 C19 1.394(3) . ?
C18 H18 0.9300 . ?
C19 C20 1.479(3) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 C22 1.509(4) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 C24 1.485(4) . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 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
N2 N1 C3 116.12(18) . . ?
N2 N1 C21 121.29(18) . . ?
C3 N1 C21 122.51(17) . . ?
O3 N2 N1 113.7(2) . . ?
N4 N3 C11 115.37(19) . . ?
N4 N3 C23 122.2(2) . . ?
C11 N3 C23 122.46(18) . . ?
O4 N4 N3 113.9(2) . . ?
C9 O1 C1 118.70(15) . . ?
C20 O2 C7 110.96(15) . . ?
O1 C1 C6 123.03(17) . . ?
O1 C1 C2 114.19(17) . . ?
C6 C1 C2 122.78(18) . . ?
C3 C2 C1 119.59(18) . . ?
C3 C2 H2A 120.2 . . ?
C1 C2 H2A 120.2 . . ?
C2 C3 C4 119.58(19) . . ?
C2 C3 N1 118.86(18) . . ?
C4 C3 N1 121.56(18) . . ?
C5 C4 C3 119.51(19) . . ?
C5 C4 H4 120.2 . . ?
C3 C4 H4 120.2 . . ?
C4 C5 C6 122.5(2) . . ?
C4 C5 H5 118.8 . . ?
C6 C5 H5 118.8 . . ?
C1 C6 C5 116.02(19) . . ?
C1 C6 C7 122.38(18) . . ?
C5 C6 C7 121.59(18) . . ?
O2 C7 C6 109.59(16) . . ?
O2 C7 C14 102.60(15) . . ?
C6 C7 C14 113.66(17) . . ?
O2 C7 C8 109.14(16) . . ?
C6 C7 C8 110.30(16) . . ?
C14 C7 C8 111.22(17) . . ?
C9 C8 C13 116.48(19) . . ?
C9 C8 C7 122.26(17) . . ?
C13 C8 C7 121.24(17) . . ?
O1 C9 C10 114.67(17) . . ?
O1 C9 C8 123.19(18) . . ?
C10 C9 C8 122.13(18) . . ?
C11 C10 C9 119.74(19) . . ?
C11 C10 H10 120.1 . . ?
C9 C10 H10 120.1 . . ?
C10 C11 C12 119.9(2) . . ?
C10 C11 N3 119.44(18) . . ?
C12 C11 N3 120.70(18) . . ?
C13 C12 C11 118.93(19) . . ?
C13 C12 H12 120.5 . . ?
C11 C12 H12 120.5 . . ?
C12 C13 C8 122.81(19) . . ?
C12 C13 H13 118.6 . . ?
C8 C13 H13 118.6 . . ?
C19 C14 C15 121.3(2) . . ?
C19 C14 C7 110.95(19) . . ?
C15 C14 C7 127.72(19) . . ?
C16 C15 C14 118.0(2) . . ?
C16 C15 H15 121.0 . . ?
C14 C15 H15 121.0 . . ?
C15 C16 C17 120.5(3) . . ?
C15 C16 H16 119.7 . . ?
C17 C16 H16 119.7 . . ?
C18 C17 C16 121.2(2) . . ?
C18 C17 H17 119.4 . . ?
C16 C17 H17 119.4 . . ?
C17 C18 C19 118.6(2) . . ?
C17 C18 H18 120.7 . . ?
C19 C18 H18 120.7 . . ?
C14 C19 C18 120.5(2) . . ?
C14 C19 C20 108.97(19) . . ?
C18 C19 C20 130.5(2) . . ?
O2 C20 C19 106.08(17) . . ?
O2 C20 H20A 110.5 . . ?
C19 C20 H20A 110.5 . . ?
O2 C20 H20B 110.5 . . ?
C19 C20 H20B 110.5 . . ?
H20A C20 H20B 108.7 . . ?
N1 C21 C22 113.3(2) . . ?
N1 C21 H21A 108.9 . . ?
C22 C21 H21A 108.9 . . ?
N1 C21 H21B 108.9 . . ?
C22 C21 H21B 108.9 . . ?
H21A C21 H21B 107.7 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
N3 C23 C24 113.2(3) . . ?
N3 C23 H23A 108.9 . . ?
C24 C23 H23A 108.9 . . ?
N3 C23 H23B 108.9 . . ?
C24 C23 H23B 108.9 . . ?
H23A C23 H23B 107.8 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C3 N1 N2 O3 -178.91(18) . . . . ?
C21 N1 N2 O3 -2.2(3) . . . . ?
C11 N3 N4 O4 179.1(3) . . . . ?
C23 N3 N4 O4 0.0(4) . . . . ?
C9 O1 C1 C6 -2.2(3) . . . . ?
C9 O1 C1 C2 177.83(19) . . . . ?
O1 C1 C2 C3 -179.11(18) . . . . ?
C6 C1 C2 C3 0.9(3) . . . . ?
C1 C2 C3 C4 1.1(3) . . . . ?
C1 C2 C3 N1 -179.35(18) . . . . ?
N2 N1 C3 C2 154.55(19) . . . . ?
C21 N1 C3 C2 -22.1(3) . . . . ?
N2 N1 C3 C4 -25.9(3) . . . . ?
C21 N1 C3 C4 157.4(2) . . . . ?
C2 C3 C4 C5 -1.9(3) . . . . ?
N1 C3 C4 C5 178.5(2) . . . . ?
C3 C4 C5 C6 0.8(3) . . . . ?
O1 C1 C6 C5 178.08(19) . . . . ?
C2 C1 C6 C5 -2.0(3) . . . . ?
O1 C1 C6 C7 -0.6(3) . . . . ?
C2 C1 C6 C7 179.40(19) . . . . ?
C4 C5 C6 C1 1.1(3) . . . . ?
C4 C5 C6 C7 179.7(2) . . . . ?
C20 O2 C7 C6 115.83(19) . . . . ?
C20 O2 C7 C14 -5.2(2) . . . . ?
C20 O2 C7 C8 -123.28(18) . . . . ?
C1 C6 C7 O2 123.6(2) . . . . ?
C5 C6 C7 O2 -55.0(3) . . . . ?
C1 C6 C7 C14 -122.3(2) . . . . ?
C5 C6 C7 C14 59.1(3) . . . . ?
C1 C6 C7 C8 3.4(3) . . . . ?
C5 C6 C7 C8 -175.20(19) . . . . ?
O2 C7 C8 C9 -124.3(2) . . . . ?
C6 C7 C8 C9 -3.9(3) . . . . ?
C14 C7 C8 C9 123.2(2) . . . . ?
O2 C7 C8 C13 57.3(2) . . . . ?
C6 C7 C8 C13 177.78(19) . . . . ?
C14 C7 C8 C13 -55.2(3) . . . . ?
C1 O1 C9 C10 -178.96(19) . . . . ?
C1 O1 C9 C8 1.7(3) . . . . ?
C13 C8 C9 O1 -179.98(19) . . . . ?
C7 C8 C9 O1 1.6(3) . . . . ?
C13 C8 C9 C10 0.7(3) . . . . ?
C7 C8 C9 C10 -177.72(19) . . . . ?
O1 C9 C10 C11 -178.7(2) . . . . ?
C8 C9 C10 C11 0.7(3) . . . . ?
C9 C10 C11 C12 -2.2(3) . . . . ?
C9 C10 C11 N3 177.1(2) . . . . ?
N4 N3 C11 C10 -146.9(2) . . . . ?
C23 N3 C11 C10 32.1(3) . . . . ?
N4 N3 C11 C12 32.4(3) . . . . ?
C23 N3 C11 C12 -148.6(2) . . . . ?
C10 C11 C12 C13 2.3(3) . . . . ?
N3 C11 C12 C13 -177.0(2) . . . . ?
C11 C12 C13 C8 -0.8(3) . . . . ?
C9 C8 C13 C12 -0.6(3) . . . . ?
C7 C8 C13 C12 177.8(2) . . . . ?
O2 C7 C14 C19 1.5(2) . . . . ?
C6 C7 C14 C19 -116.7(2) . . . . ?
C8 C7 C14 C19 118.08(19) . . . . ?
O2 C7 C14 C15 -175.7(2) . . . . ?
C6 C7 C14 C15 66.0(3) . . . . ?
C8 C7 C14 C15 -59.2(3) . . . . ?
C19 C14 C15 C16 -0.7(4) . . . . ?
C7 C14 C15 C16 176.3(2) . . . . ?
C14 C15 C16 C17 0.8(4) . . . . ?
C15 C16 C17 C18 -0.7(5) . . . . ?
C16 C17 C18 C19 0.4(4) . . . . ?
C15 C14 C19 C18 0.5(3) . . . . ?
C7 C14 C19 C18 -177.0(2) . . . . ?
C15 C14 C19 C20 -179.9(2) . . . . ?
C7 C14 C19 C20 2.6(3) . . . . ?
C17 C18 C19 C14 -0.3(4) . . . . ?
C17 C18 C19 C20 -179.8(2) . . . . ?
C7 O2 C20 C19 6.9(2) . . . . ?
C14 C19 C20 O2 -5.8(2) . . . . ?
C18 C19 C20 O2 173.7(2) . . . . ?
N2 N1 C21 C22 -80.8(3) . . . . ?
C3 N1 C21 C22 95.8(2) . . . . ?
N4 N3 C23 C24 81.8(3) . . . . ?
C11 N3 C23 C24 -97.2(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C21 H21A O2 0.97 2.62 3.506(3) 151.8 4_565
C12 H12 O4 0.93 2.51 3.404(3) 161.1 3_656
C12 H12 O4 0.93 2.51 3.404(3) 161.1 3_656
C21 H21A O2 0.97 2.62 3.506(3) 151.8 4_565

_refine_diff_density_max         0.310
_refine_diff_density_min         -0.275
_refine_diff_density_rms         0.035

_shelxl_version_number           2013-4



####################################################################### 
# 
# 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_d8v17769
_database_code_depnum_ccdc_archive 'CCDC 1860103'
_audit_update_record             
;
2018-08-03 deposited with the CCDC.
2018-09-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C12 H12 N2 O3'
_chemical_formula_weight         232.24

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           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   11.2278(5)
_cell_length_b                   13.7389(6)
_cell_length_c                   7.4364(3)
_cell_angle_alpha                90
_cell_angle_beta                 107.1730(10)
_cell_angle_gamma                90
_cell_volume                     1095.98(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    6795
_cell_measurement_theta_min      4.818
_cell_measurement_theta_max      54.846

_exptl_crystal_description       prismatic
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.407
_exptl_crystal_F_000             488
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.103
_shelx_estimated_absorpt_T_min   0.980
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6637
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            18997
_diffrn_reflns_av_unetI/netI     0.0304
_diffrn_reflns_av_R_equivalents  0.0617
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         2.409
_diffrn_reflns_theta_max         25.996
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             2146
_reflns_number_gt                1794
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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-2013 (Sheldrick, 2013)'
_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)+(0.0380P)²+0.3915P] 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
_refine_ls_extinction_coef       0.032(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2146
_refine_ls_number_parameters     157
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0500
_refine_ls_R_factor_gt           0.0387
_refine_ls_wR_factor_ref         0.0998
_refine_ls_wR_factor_gt          0.0914
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_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
N1 N 0.87114(10) 0.71962(9) 0.75006(16) 0.0292(3) Uani 1 1 d . . . . .
N2 N 0.95088(12) 0.79447(10) 0.77870(19) 0.0396(4) Uani 1 1 d . . . . .
O1 O 0.29923(10) 0.54689(8) 0.18893(17) 0.0490(4) Uani 1 1 d . . . . .
O2 O 0.47516(9) 0.60817(7) 0.36879(14) 0.0342(3) Uani 1 1 d . . . . .
O3 O 1.05852(10) 0.77443(9) 0.87148(17) 0.0496(4) Uani 1 1 d . . . . .
C1 C 0.35621(13) 0.62057(11) 0.2485(2) 0.0334(4) Uani 1 1 d . . . . .
C2 C 0.31231(13) 0.71843(11) 0.2044(2) 0.0307(3) Uani 1 1 d . . . . .
H2 H 0.2303 0.7281 0.1230 0.037 Uiso 1 1 calc R U . . .
C3 C 0.38270(13) 0.79706(10) 0.27381(19) 0.0277(3) Uani 1 1 d . . . . .
C4 C 0.50742(12) 0.78190(10) 0.39934(19) 0.0252(3) Uani 1 1 d . . . . .
C5 C 0.54943(12) 0.68711(10) 0.44246(19) 0.0261(3) Uani 1 1 d . . . . .
C6 C 0.66747(13) 0.66485(10) 0.55831(19) 0.0284(3) Uani 1 1 d . . . . .
H6 H 0.6927 0.5991 0.5844 0.034 Uiso 1 1 calc R U . . .
C7 C 0.74802(13) 0.74049(10) 0.63532(19) 0.0264(3) Uani 1 1 d . . . . .
C8 C 0.70840(13) 0.83713(11) 0.59823(19) 0.0303(3) Uani 1 1 d . . . . .
H8 H 0.7627 0.8891 0.6532 0.036 Uiso 1 1 calc R U . . .
C9 C 0.59084(13) 0.85639(11) 0.4822(2) 0.0297(3) Uani 1 1 d . . . . .
H9 H 0.5653 0.9222 0.4572 0.036 Uiso 1 1 calc R U . . .
C10 C 0.33394(14) 0.89831(11) 0.2242(2) 0.0386(4) Uani 1 1 d . . . . .
H10A H 0.2563 0.8956 0.1204 0.058 Uiso 1 1 calc R U . . .
H10B H 0.3958 0.9368 0.1858 0.058 Uiso 1 1 calc R U . . .
H10C H 0.3179 0.9287 0.3340 0.058 Uiso 1 1 calc R U . . .
C11 C 0.91213(14) 0.62194(11) 0.8227(2) 0.0345(4) Uani 1 1 d . . . . .
H11A H 0.8407 0.5865 0.8438 0.041 Uiso 1 1 calc R U . . .
H11B H 0.9771 0.6281 0.9455 0.041 Uiso 1 1 calc R U . . .
C12 C 0.96387(17) 0.56337(13) 0.6897(3) 0.0503(5) Uani 1 1 d . . . . .
H12A H 0.8999 0.5569 0.5679 0.075 Uiso 1 1 calc R U . . .
H12B H 0.9884 0.4986 0.7430 0.075 Uiso 1 1 calc R U . . .
H12C H 1.0368 0.5968 0.6722 0.075 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
N1 N2 1.3385(17) . ?
N1 C7 1.4229(17) . ?
N1 C11 1.4689(19) . ?
N2 O3 1.2329(16) . ?
O1 C1 1.2095(18) . ?
O2 C5 1.3791(16) . ?
O2 C1 1.3811(17) . ?
C1 C2 1.436(2) . ?
C2 C3 1.348(2) . ?
C2 H2 0.9500 . ?
C3 C4 1.4504(19) . ?
C3 C10 1.500(2) . ?
C4 C5 1.3900(19) . ?
C4 C9 1.4012(19) . ?
C5 C6 1.3849(19) . ?
C6 C7 1.386(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.402(2) . ?
C8 C9 1.3728(19) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C11 C12 1.517(2) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?

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
N2 N1 C7 115.24(11) . . ?
N2 N1 C11 121.41(11) . . ?
C7 N1 C11 123.23(12) . . ?
O3 N2 N1 114.62(13) . . ?
C5 O2 C1 121.06(11) . . ?
O1 C1 O2 116.08(13) . . ?
O1 C1 C2 126.24(13) . . ?
O2 C1 C2 117.67(12) . . ?
C3 C2 C1 122.68(13) . . ?
C3 C2 H2 118.7 . . ?
C1 C2 H2 118.7 . . ?
C2 C3 C4 118.47(13) . . ?
C2 C3 C10 121.24(13) . . ?
C4 C3 C10 120.28(12) . . ?
C5 C4 C9 116.47(12) . . ?
C5 C4 C3 118.71(12) . . ?
C9 C4 C3 124.82(13) . . ?
O2 C5 C6 115.39(12) . . ?
O2 C5 C4 121.40(12) . . ?
C6 C5 C4 123.20(13) . . ?
C5 C6 C7 118.65(13) . . ?
C5 C6 H6 120.7 . . ?
C7 C6 H6 120.7 . . ?
C6 C7 C8 119.91(12) . . ?
C6 C7 N1 119.78(12) . . ?
C8 C7 N1 120.30(12) . . ?
C9 C8 C7 119.78(13) . . ?
C9 C8 H8 120.1 . . ?
C7 C8 H8 120.1 . . ?
C8 C9 C4 121.97(13) . . ?
C8 C9 H9 119.0 . . ?
C4 C9 H9 119.0 . . ?
C3 C10 H10A 109.5 . . ?
C3 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C3 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N1 C11 C12 112.56(13) . . ?
N1 C11 H11A 109.1 . . ?
C12 C11 H11A 109.1 . . ?
N1 C11 H11B 109.1 . . ?
C12 C11 H11B 109.1 . . ?
H11A C11 H11B 107.8 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C11 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7 N1 N2 O3 -177.01(13) . . . . ?
C11 N1 N2 O3 -1.0(2) . . . . ?
C5 O2 C1 O1 178.81(13) . . . . ?
C5 O2 C1 C2 -0.58(19) . . . . ?
O1 C1 C2 C3 -178.59(15) . . . . ?
O2 C1 C2 C3 0.7(2) . . . . ?
C1 C2 C3 C4 -0.5(2) . . . . ?
C1 C2 C3 C10 179.79(14) . . . . ?
C2 C3 C4 C5 0.22(19) . . . . ?
C10 C3 C4 C5 179.89(13) . . . . ?
C2 C3 C4 C9 -179.91(13) . . . . ?
C10 C3 C4 C9 -0.2(2) . . . . ?
C1 O2 C5 C6 -178.83(12) . . . . ?
C1 O2 C5 C4 0.29(19) . . . . ?
C9 C4 C5 O2 -179.97(12) . . . . ?
C3 C4 C5 O2 -0.09(19) . . . . ?
C9 C4 C5 C6 -0.9(2) . . . . ?
C3 C4 C5 C6 178.96(12) . . . . ?
O2 C5 C6 C7 179.08(12) . . . . ?
C4 C5 C6 C7 0.0(2) . . . . ?
C5 C6 C7 C8 1.2(2) . . . . ?
C5 C6 C7 N1 -178.04(12) . . . . ?
N2 N1 C7 C6 163.93(13) . . . . ?
C11 N1 C7 C6 -12.04(19) . . . . ?
N2 N1 C7 C8 -15.36(18) . . . . ?
C11 N1 C7 C8 168.67(13) . . . . ?
C6 C7 C8 C9 -1.5(2) . . . . ?
N1 C7 C8 C9 177.79(13) . . . . ?
C7 C8 C9 C4 0.5(2) . . . . ?
C5 C4 C9 C8 0.7(2) . . . . ?
C3 C4 C9 C8 -179.20(13) . . . . ?
N2 N1 C11 C12 -85.95(17) . . . . ?
C7 N1 C11 C12 89.77(16) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C11 H11A O1 0.99 2.38 3.3012(19) 154.7 3_666
C6 H6 O1 0.95 2.60 3.4235(18) 144.7 3_666
C2 H2 O3 0.95 2.34 3.2673(17) 163.9 1_454

_refine_diff_density_max         0.211
_refine_diff_density_min         -0.154
_refine_diff_density_rms         0.035

_shelxl_version_number           2013-4



####################################################################### 
# 
# 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_d8v17683
_database_code_depnum_ccdc_archive 'CCDC 1860104'
_audit_update_record             
;
2018-08-03 deposited with the CCDC.
2018-09-13 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C24 H20 N4 O5'
_chemical_formula_weight         444.44

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           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   13.1450(5)
_cell_length_b                   14.0218(6)
_cell_length_c                   12.9264(5)
_cell_angle_alpha                90
_cell_angle_beta                 114.4160(10)
_cell_angle_gamma                90
_cell_volume                     2169.47(15)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    9963
_cell_measurement_theta_min      4.718
_cell_measurement_theta_max      54.467

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_F_000             928
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.098
_shelx_estimated_absorpt_T_min   0.983
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6733
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            47168
_diffrn_reflns_av_unetI/netI     0.0316
_diffrn_reflns_av_R_equivalents  0.0732
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.359
_diffrn_reflns_theta_max         26.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4256
_reflns_number_gt                3297
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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-2013 (Sheldrick, 2013)'
_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)+(0.0354P)²+0.9505P] 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
_refine_ls_extinction_coef       0.0152(12)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         4256
_refine_ls_number_parameters     301
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0592
_refine_ls_R_factor_gt           0.0411
_refine_ls_wR_factor_ref         0.1004
_refine_ls_wR_factor_gt          0.0889
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_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
N1 N 0.28064(11) 0.56794(10) 0.15217(11) 0.0317(3) Uani 1 1 d . . . . .
N2 N 0.17371(13) 0.58405(12) 0.08379(13) 0.0467(4) Uani 1 1 d . . . . .
N3 N 0.82031(11) 0.19280(10) 0.72824(12) 0.0328(3) Uani 1 1 d . . . . .
N4 N 0.89452(12) 0.25471(12) 0.71976(12) 0.0422(4) Uani 1 1 d . . . . .
O1 O 0.29582(12) 0.41059(10) 0.75329(12) 0.0541(4) Uani 1 1 d . . . . .
O2 O 0.37436(9) 0.39445(8) 0.63082(9) 0.0308(3) Uani 1 1 d . . . . .
O3 O 0.53602(8) 0.38043(8) 0.45268(9) 0.0306(3) Uani 1 1 d . . . . .
O4 O 0.16025(11) 0.63435(12) 0.00053(12) 0.0596(4) Uani 1 1 d . . . . .
O5 O 0.99201(10) 0.22648(11) 0.76390(11) 0.0534(4) Uani 1 1 d . . . . .
C1 C 0.30069(14) 0.36748(13) 0.67452(15) 0.0358(4) Uani 1 1 d . . . . .
C2 C 0.23846(13) 0.28455(13) 0.61121(14) 0.0339(4) Uani 1 1 d . . . . .
C3 C 0.15225(15) 0.23455(15) 0.62176(18) 0.0479(5) Uani 1 1 d . . . . .
H3 H 0.1254 0.2517 0.6771 0.058 Uiso 1 1 calc R U . . .
C4 C 0.10726(15) 0.15926(16) 0.54909(19) 0.0548(6) Uani 1 1 d . . . . .
H4A H 0.0479 0.1236 0.5539 0.066 Uiso 1 1 calc R U . . .
C5 C 0.14721(15) 0.13448(15) 0.46874(17) 0.0495(5) Uani 1 1 d . . . . .
H5A H 0.1144 0.0821 0.4196 0.059 Uiso 1 1 calc R U . . .
C6 C 0.23375(14) 0.18416(13) 0.45833(15) 0.0371(4) Uani 1 1 d . . . . .
H6 H 0.2612 0.1667 0.4036 0.045 Uiso 1 1 calc R U . . .
C7 C 0.27822(12) 0.26011(12) 0.53098(13) 0.0286(4) Uani 1 1 d . . . . .
C8 C 0.36988(12) 0.32795(11) 0.53826(13) 0.0264(3) Uani 1 1 d . . . . .
C9 C 0.34414(13) 0.38751(11) 0.43383(13) 0.0268(3) Uani 1 1 d . . . . .
C10 C 0.42699(12) 0.41125(11) 0.39849(13) 0.0259(3) Uani 1 1 d . . . . .
C11 C 0.40640(13) 0.46947(11) 0.30504(13) 0.0277(3) Uani 1 1 d . . . . .
H11 H 0.4644 0.4833 0.2816 0.033 Uiso 1 1 calc R U . . .
C12 C 0.30099(13) 0.50696(11) 0.24665(13) 0.0280(3) Uani 1 1 d . . . . .
C13 C 0.21562(14) 0.48557(12) 0.28112(14) 0.0342(4) Uani 1 1 d . . . . .
H13 H 0.1431 0.5119 0.2419 0.041 Uiso 1 1 calc R U . . .
C14 C 0.23801(13) 0.42601(12) 0.37228(14) 0.0334(4) Uani 1 1 d . . . . .
H14 H 0.1794 0.4105 0.3942 0.040 Uiso 1 1 calc R U . . .
C15 C 0.48428(12) 0.28377(11) 0.57892(13) 0.0255(3) Uani 1 1 d . . . . .
C16 C 0.56236(13) 0.31659(11) 0.54064(13) 0.0256(3) Uani 1 1 d . . . . .
C17 C 0.67278(12) 0.28678(11) 0.58828(13) 0.0277(3) Uani 1 1 d . . . . .
H17 H 0.7244 0.3111 0.5608 0.033 Uiso 1 1 calc R U . . .
C18 C 0.70695(12) 0.22139(11) 0.67608(13) 0.0281(4) Uani 1 1 d . . . . .
C19 C 0.62946(13) 0.18365(12) 0.71315(14) 0.0314(4) Uani 1 1 d . . . . .
H19 H 0.6518 0.1367 0.7713 0.038 Uiso 1 1 calc R U . . .
C20 C 0.52046(13) 0.21499(12) 0.66489(14) 0.0304(4) Uani 1 1 d . . . . .
H20 H 0.4683 0.1891 0.6908 0.037 Uiso 1 1 calc R U . . .
C21 C 0.37020(14) 0.60807(12) 0.12649(14) 0.0346(4) Uani 1 1 d . . . . .
H21A H 0.4377 0.6161 0.1982 0.042 Uiso 1 1 calc R U . . .
H21B H 0.3473 0.6720 0.0922 0.042 Uiso 1 1 calc R U . . .
C22 C 0.39892(17) 0.54656(14) 0.04641(16) 0.0454(5) Uani 1 1 d . . . . .
H22A H 0.4252 0.4842 0.0814 0.068 Uiso 1 1 calc R U . . .
H22B H 0.4578 0.5775 0.0306 0.068 Uiso 1 1 calc R U . . .
H22C H 0.3324 0.5381 -0.0248 0.068 Uiso 1 1 calc R U . . .
C23 C 0.85581(16) 0.10111(14) 0.78488(19) 0.0533(6) Uani 1 1 d . . . . .
H23A H 0.9175 0.0758 0.7679 0.064 Uiso 1 1 calc R U . . .
H23B H 0.7928 0.0556 0.7542 0.064 Uiso 1 1 calc R U . . .
C24 C 0.8946(2) 0.1080(2) 0.9125(2) 0.0846(9) Uani 1 1 d . . . . .
H24A H 0.9607 0.1491 0.9442 0.127 Uiso 1 1 calc R U . . .
H24B H 0.9135 0.0442 0.9461 0.127 Uiso 1 1 calc R U . . .
H24C H 0.8347 0.1351 0.9299 0.127 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
N1 N2 1.3345(19) . ?
N1 C12 1.423(2) . ?
N1 C21 1.461(2) . ?
N2 O4 1.2368(19) . ?
N3 N4 1.344(2) . ?
N3 C18 1.416(2) . ?
N3 C23 1.457(2) . ?
N4 O5 1.2330(19) . ?
O1 C1 1.208(2) . ?
O2 C1 1.3609(19) . ?
O2 C8 1.4988(18) . ?
O3 C16 1.3743(18) . ?
O3 C10 1.3789(18) . ?
C1 C2 1.462(3) . ?
C2 C7 1.384(2) . ?
C2 C3 1.386(2) . ?
C3 C4 1.374(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.388(3) . ?
C4 H4A 0.9500 . ?
C5 C6 1.387(2) . ?
C5 H5A 0.9500 . ?
C6 C7 1.380(2) . ?
C6 H6 0.9500 . ?
C7 C8 1.507(2) . ?
C8 C9 1.502(2) . ?
C8 C15 1.506(2) . ?
C9 C10 1.384(2) . ?
C9 C14 1.398(2) . ?
C10 C11 1.389(2) . ?
C11 C12 1.379(2) . ?
C11 H11 0.9500 . ?
C12 C13 1.400(2) . ?
C13 C14 1.373(2) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 C16 1.389(2) . ?
C15 C20 1.398(2) . ?
C16 C17 1.386(2) . ?
C17 C18 1.382(2) . ?
C17 H17 0.9500 . ?
C18 C19 1.397(2) . ?
C19 C20 1.377(2) . ?
C19 H19 0.9500 . ?
C20 H20 0.9500 . ?
C21 C22 1.510(2) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 C24 1.516(3) . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?

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
N2 N1 C12 116.30(13) . . ?
N2 N1 C21 120.74(13) . . ?
C12 N1 C21 122.90(13) . . ?
O4 N2 N1 113.92(14) . . ?
N4 N3 C18 115.77(14) . . ?
N4 N3 C23 121.23(14) . . ?
C18 N3 C23 122.98(14) . . ?
O5 N4 N3 113.92(16) . . ?
C1 O2 C8 111.01(12) . . ?
C16 O3 C10 118.55(11) . . ?
O1 C1 O2 120.35(17) . . ?
O1 C1 C2 131.09(16) . . ?
O2 C1 C2 108.56(14) . . ?
C7 C2 C3 121.73(18) . . ?
C7 C2 C1 108.61(14) . . ?
C3 C2 C1 129.65(17) . . ?
C4 C3 C2 117.37(18) . . ?
C4 C3 H3 121.3 . . ?
C2 C3 H3 121.3 . . ?
C3 C4 C5 121.00(18) . . ?
C3 C4 H4A 119.5 . . ?
C5 C4 H4A 119.5 . . ?
C6 C5 C4 121.7(2) . . ?
C6 C5 H5A 119.1 . . ?
C4 C5 H5A 119.1 . . ?
C7 C6 C5 117.08(18) . . ?
C7 C6 H6 121.5 . . ?
C5 C6 H6 121.5 . . ?
C6 C7 C2 121.08(15) . . ?
C6 C7 C8 129.23(14) . . ?
C2 C7 C8 109.69(14) . . ?
O2 C8 C9 106.95(12) . . ?
O2 C8 C15 105.86(12) . . ?
C9 C8 C15 111.34(12) . . ?
O2 C8 C7 102.06(11) . . ?
C9 C8 C7 114.68(13) . . ?
C15 C8 C7 114.79(13) . . ?
C10 C9 C14 117.10(14) . . ?
C10 C9 C8 120.96(14) . . ?
C14 C9 C8 121.83(13) . . ?
O3 C10 C9 123.45(14) . . ?
O3 C10 C11 114.46(13) . . ?
C9 C10 C11 122.09(14) . . ?
C12 C11 C10 119.39(14) . . ?
C12 C11 H11 120.3 . . ?
C10 C11 H11 120.3 . . ?
C11 C12 C13 120.01(14) . . ?
C11 C12 N1 119.26(13) . . ?
C13 C12 N1 120.72(14) . . ?
C14 C13 C12 119.18(15) . . ?
C14 C13 H13 120.4 . . ?
C12 C13 H13 120.4 . . ?
C13 C14 C9 122.20(15) . . ?
C13 C14 H14 118.9 . . ?
C9 C14 H14 118.9 . . ?
C16 C15 C20 116.93(14) . . ?
C16 C15 C8 121.17(14) . . ?
C20 C15 C8 121.59(13) . . ?
O3 C16 C17 115.04(13) . . ?
O3 C16 C15 122.68(13) . . ?
C17 C16 C15 122.28(14) . . ?
C18 C17 C16 119.35(14) . . ?
C18 C17 H17 120.3 . . ?
C16 C17 H17 120.3 . . ?
C17 C18 C19 119.85(14) . . ?
C17 C18 N3 119.99(14) . . ?
C19 C18 N3 120.17(14) . . ?
C20 C19 C18 119.57(15) . . ?
C20 C19 H19 120.2 . . ?
C18 C19 H19 120.2 . . ?
C19 C20 C15 121.91(14) . . ?
C19 C20 H20 119.0 . . ?
C15 C20 H20 119.0 . . ?
N1 C21 C22 112.88(15) . . ?
N1 C21 H21A 109.0 . . ?
C22 C21 H21A 109.0 . . ?
N1 C21 H21B 109.0 . . ?
C22 C21 H21B 109.0 . . ?
H21A C21 H21B 107.8 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
N3 C23 C24 112.62(19) . . ?
N3 C23 H23A 109.1 . . ?
C24 C23 H23A 109.1 . . ?
N3 C23 H23B 109.1 . . ?
C24 C23 H23B 109.1 . . ?
H23A C23 H23B 107.8 . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C12 N1 N2 O4 -177.30(15) . . . . ?
C21 N1 N2 O4 0.0(2) . . . . ?
C18 N3 N4 O5 -178.45(14) . . . . ?
C23 N3 N4 O5 -0.3(2) . . . . ?
C8 O2 C1 O1 177.02(15) . . . . ?
C8 O2 C1 C2 -2.68(17) . . . . ?
O1 C1 C2 C7 -177.80(18) . . . . ?
O2 C1 C2 C7 1.85(18) . . . . ?
O1 C1 C2 C3 3.0(3) . . . . ?
O2 C1 C2 C3 -177.30(17) . . . . ?
C7 C2 C3 C4 0.0(3) . . . . ?
C1 C2 C3 C4 179.02(17) . . . . ?
C2 C3 C4 C5 0.2(3) . . . . ?
C3 C4 C5 C6 0.1(3) . . . . ?
C4 C5 C6 C7 -0.5(3) . . . . ?
C5 C6 C7 C2 0.6(2) . . . . ?
C5 C6 C7 C8 -178.57(16) . . . . ?
C3 C2 C7 C6 -0.4(2) . . . . ?
C1 C2 C7 C6 -179.63(15) . . . . ?
C3 C2 C7 C8 178.95(15) . . . . ?
C1 C2 C7 C8 -0.29(18) . . . . ?
C1 O2 C8 C9 123.16(13) . . . . ?
C1 O2 C8 C15 -118.03(13) . . . . ?
C1 O2 C8 C7 2.40(15) . . . . ?
C6 C7 C8 O2 178.08(15) . . . . ?
C2 C7 C8 O2 -1.20(16) . . . . ?
C6 C7 C8 C9 62.9(2) . . . . ?
C2 C7 C8 C9 -116.43(15) . . . . ?
C6 C7 C8 C15 -67.9(2) . . . . ?
C2 C7 C8 C15 112.79(15) . . . . ?
O2 C8 C9 C10 103.20(15) . . . . ?
C15 C8 C9 C10 -12.0(2) . . . . ?
C7 C8 C9 C10 -144.44(15) . . . . ?
O2 C8 C9 C14 -72.90(18) . . . . ?
C15 C8 C9 C14 171.91(15) . . . . ?
C7 C8 C9 C14 39.5(2) . . . . ?
C16 O3 C10 C9 5.5(2) . . . . ?
C16 O3 C10 C11 -175.04(13) . . . . ?
C14 C9 C10 O3 178.39(14) . . . . ?
C8 C9 C10 O3 2.1(2) . . . . ?
C14 C9 C10 C11 -1.0(2) . . . . ?
C8 C9 C10 C11 -177.26(14) . . . . ?
O3 C10 C11 C12 -177.89(14) . . . . ?
C9 C10 C11 C12 1.5(2) . . . . ?
C10 C11 C12 C13 -0.5(2) . . . . ?
C10 C11 C12 N1 178.90(14) . . . . ?
N2 N1 C12 C11 165.01(15) . . . . ?
C21 N1 C12 C11 -12.2(2) . . . . ?
N2 N1 C12 C13 -15.5(2) . . . . ?
C21 N1 C12 C13 167.22(15) . . . . ?
C11 C12 C13 C14 -0.9(2) . . . . ?
N1 C12 C13 C14 179.63(15) . . . . ?
C12 C13 C14 C9 1.5(3) . . . . ?
C10 C9 C14 C13 -0.6(2) . . . . ?
C8 C9 C14 C13 175.68(15) . . . . ?
O2 C8 C15 C16 -100.21(15) . . . . ?
C9 C8 C15 C16 15.7(2) . . . . ?
C7 C8 C15 C16 148.04(14) . . . . ?
O2 C8 C15 C20 73.21(17) . . . . ?
C9 C8 C15 C20 -170.93(14) . . . . ?
C7 C8 C15 C20 -38.5(2) . . . . ?
C10 O3 C16 C17 178.03(13) . . . . ?
C10 O3 C16 C15 -1.7(2) . . . . ?
C20 C15 C16 O3 176.59(14) . . . . ?
C8 C15 C16 O3 -9.7(2) . . . . ?
C20 C15 C16 C17 -3.1(2) . . . . ?
C8 C15 C16 C17 170.63(14) . . . . ?
O3 C16 C17 C18 -178.96(13) . . . . ?
C15 C16 C17 C18 0.7(2) . . . . ?
C16 C17 C18 C19 2.2(2) . . . . ?
C16 C17 C18 N3 -177.80(14) . . . . ?
N4 N3 C18 C17 24.0(2) . . . . ?
C23 N3 C18 C17 -154.14(17) . . . . ?
N4 N3 C18 C19 -156.00(15) . . . . ?
C23 N3 C18 C19 25.9(2) . . . . ?
C17 C18 C19 C20 -2.7(2) . . . . ?
N3 C18 C19 C20 177.33(15) . . . . ?
C18 C19 C20 C15 0.2(2) . . . . ?
C16 C15 C20 C19 2.6(2) . . . . ?
C8 C15 C20 C19 -171.09(15) . . . . ?
N2 N1 C21 C22 -85.5(2) . . . . ?
C12 N1 C21 C22 91.66(18) . . . . ?
N4 N3 C23 C24 84.1(2) . . . . ?
C18 N3 C23 C24 -97.8(2) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
C23 H23B O1 0.99 2.32 3.246(2) 154.5 2_646
C21 H21A O2 0.99 2.55 3.523(2) 168.0 3_666
C11 H11 O2 0.95 2.59 3.2647(19) 127.9 3_666
C11 H11 O2 0.95 2.59 3.2647(19) 127.9 3_666
C21 H21A O2 0.99 2.55 3.523(2) 168.0 3_666
C23 H23B O1 0.99 2.32 3.246(2) 154.5 2_646

_refine_diff_density_max         0.205
_refine_diff_density_min         -0.196
_refine_diff_density_rms         0.040

_shelxl_version_number           2013-4



