# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
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# 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 
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data_testm1
_database_code_depnum_ccdc_archive 'CCDC 1867365'
_audit_update_record             
;
2018-09-12 deposited with the CCDC.
2019-02-04 downloaded from the CCDC.
;
_audit_creation_date             2018-05-31
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C21 H24 N4 O3'
_chemical_formula_sum            'C21 H24 N4 O3'
_chemical_formula_weight         380.44
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   22.4783(5)
_cell_length_b                   11.4618(2)
_cell_length_c                   15.6035(4)
_cell_angle_alpha                90
_cell_angle_beta                 92.056(2)
_cell_angle_gamma                90
_cell_volume                     4017.53(15)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4349
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.82
_cell_measurement_theta_min      2.37
_shelx_estimated_absorpt_T_max   0.977
_shelx_estimated_absorpt_T_min   0.953
_exptl_absorpt_coefficient_mu    0.086
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6264
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0590 before and 0.0430 after correction. The Ratio of minimum to maximum transmission is 0.8401. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.258
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1616
_exptl_crystal_size_max          0.561
_exptl_crystal_size_mid          0.292
_exptl_crystal_size_min          0.275
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0360
_diffrn_reflns_av_unetI/netI     0.0346
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       29
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            17959
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.949
_diffrn_reflns_theta_min         1.995
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Bruker area detector'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'Bruker Apex II kappa CCD area detector'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3669
_reflns_number_total             4827
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       'Bruker Apex suite'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.345
_refine_diff_density_min         -0.285
_refine_diff_density_rms         0.047
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     262
_refine_ls_number_reflns         4827
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0619
_refine_ls_R_factor_gt           0.0430
_refine_ls_restrained_S_all      1.025
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0508P)²+3.2786P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1030
_refine_ls_wR_factor_ref         0.1129
_refine_special_details          
;
The N-H hydrogen atom was located in the difference map and refined freely.
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C1(H1), C2(H2), C4(H4), C5(H5), C16(H16), C17(H17), C19(H19), C20(H20)
2.b Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C11(H11A,H11B,H11C), C12(H12A,H12B,H12C), C14(H14A,H14B,
 H14C), C21(H21A,H21B,H21C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.19693(5) 0.01096(8) 0.75026(7) 0.0225(2) Uani 1 1 d . . . . .
O2 O 0.34965(5) 0.23397(9) 0.86051(7) 0.0226(2) Uani 1 1 d . . . . .
O3 O 0.40957(5) 0.14295(8) 0.68303(7) 0.0216(2) Uani 1 1 d . . . . .
N1 N 0.26689(6) 0.11765(10) 0.82791(8) 0.0176(3) Uani 1 1 d . . . . .
N2 N 0.30365(5) 0.22657(10) 0.72564(7) 0.0147(2) Uani 1 1 d . . . . .
N3 N 0.34313(5) 0.29515(10) 0.68201(8) 0.0153(2) Uani 1 1 d . . . . .
N4 N 0.44133(6) 0.32457(10) 0.64725(9) 0.0205(3) Uani 1 1 d . . . . .
C1 C 0.18633(7) 0.33139(12) 0.71839(9) 0.0175(3) Uani 1 1 d . . . . .
H1 H 0.208877 0.339519 0.770713 0.021 Uiso 1 1 calc R . . . .
C2 C 0.13764(7) 0.40321(12) 0.70234(9) 0.0188(3) Uani 1 1 d . . . . .
H2 H 0.127068 0.459523 0.743796 0.023 Uiso 1 1 calc R . . . .
C3 C 0.10400(7) 0.39352(12) 0.62578(10) 0.0216(3) Uani 1 1 d . . . . .
C4 C 0.12098(7) 0.31118(14) 0.56652(10) 0.0250(3) Uani 1 1 d . . . . .
H4 H 0.098963 0.304261 0.513651 0.030 Uiso 1 1 calc R . . . .
C5 C 0.16968(7) 0.23823(13) 0.58279(10) 0.0211(3) Uani 1 1 d . . . . .
H5 H 0.180200 0.181919 0.541307 0.025 Uiso 1 1 calc R . . . .
C6 C 0.20288(6) 0.24728(11) 0.65909(9) 0.0150(3) Uani 1 1 d . . . . .
C7 C 0.05123(8) 0.47266(15) 0.60904(12) 0.0335(4) Uani 1 1 d . . . . .
H7A H 0.024847 0.468869 0.657616 0.050 Uiso 1 1 calc GR . . . .
H7B H 0.029468 0.447515 0.556718 0.050 Uiso 1 1 calc GR . . . .
H7C H 0.065109 0.553018 0.601919 0.050 Uiso 1 1 calc GR . . . .
C8 C 0.25438(6) 0.16432(11) 0.68241(9) 0.0144(3) Uani 1 1 d . . . . .
C9 C 0.23469(6) 0.08674(12) 0.75597(9) 0.0163(3) Uani 1 1 d . . . . .
C10 C 0.31217(6) 0.19830(12) 0.80978(9) 0.0161(3) Uani 1 1 d . . . . .
C11 C 0.27457(7) 0.08823(12) 0.60870(9) 0.0205(3) Uani 1 1 d . . . . .
H11A H 0.284714 0.137913 0.560242 0.031 Uiso 1 1 calc GR . . . .
H11B H 0.242349 0.034946 0.590890 0.031 Uiso 1 1 calc GR . . . .
H11C H 0.309616 0.042955 0.627622 0.031 Uiso 1 1 calc GR . . . .
C12 C 0.26044(8) 0.06563(14) 0.91220(10) 0.0244(3) Uani 1 1 d . . . . .
H12A H 0.218082 0.059171 0.924269 0.037 Uiso 1 1 calc GR . . . .
H12B H 0.280373 0.114890 0.955804 0.037 Uiso 1 1 calc GR . . . .
H12C H 0.278530 -0.012173 0.913276 0.037 Uiso 1 1 calc GR . . . .
C13 C 0.39975(6) 0.24679(12) 0.67241(9) 0.0160(3) Uani 1 1 d . . . . .
C14 C 0.50080(7) 0.28133(14) 0.62961(12) 0.0273(4) Uani 1 1 d . . . . .
H14A H 0.509519 0.212339 0.664971 0.041 Uiso 1 1 calc GR . . . .
H14B H 0.530259 0.342236 0.643175 0.041 Uiso 1 1 calc GR . . . .
H14C H 0.502524 0.260424 0.568850 0.041 Uiso 1 1 calc GR . . . .
C15 C 0.42840(6) 0.44545(12) 0.62942(10) 0.0181(3) Uani 1 1 d . . . . .
C16 C 0.41423(7) 0.48101(13) 0.54608(10) 0.0214(3) Uani 1 1 d . . . . .
H16 H 0.412935 0.425588 0.500785 0.026 Uiso 1 1 calc R . . . .
C17 C 0.40196(7) 0.59761(13) 0.52901(10) 0.0220(3) Uani 1 1 d . . . . .
H17 H 0.391338 0.621051 0.472102 0.026 Uiso 1 1 calc R . . . .
C18 C 0.40501(7) 0.68065(12) 0.59416(10) 0.0207(3) Uani 1 1 d . . . . .
C19 C 0.42054(7) 0.64437(13) 0.67684(10) 0.0218(3) Uani 1 1 d . . . . .
H19 H 0.423603 0.700161 0.721802 0.026 Uiso 1 1 calc R . . . .
C20 C 0.43169(7) 0.52718(13) 0.69468(10) 0.0203(3) Uani 1 1 d . . . . .
H20 H 0.441575 0.503321 0.751733 0.024 Uiso 1 1 calc R . . . .
C21 C 0.39062(8) 0.80730(13) 0.57503(11) 0.0299(4) Uani 1 1 d . . . . .
H21A H 0.398758 0.824331 0.515029 0.045 Uiso 1 1 calc GR . . . .
H21B H 0.415318 0.857572 0.612604 0.045 Uiso 1 1 calc GR . . . .
H21C H 0.348493 0.821950 0.585090 0.045 Uiso 1 1 calc GR . . . .
H3 H 0.3392(8) 0.3679(17) 0.6930(12) 0.029(5) Uiso 1 1 d . . . . .


_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
O1 C9 1.2154(17) . ?
O2 C10 1.2065(17) . ?
O3 C13 1.2207(17) . ?
N1 C9 1.3605(18) . ?
N1 C10 1.4112(18) . ?
N1 C12 1.4560(18) . ?
N2 N3 1.3827(16) . ?
N2 C8 1.4619(17) . ?
N2 C10 1.3591(18) . ?
N3 C13 1.4012(18) . ?
N3 H3 0.857(19) . ?
N4 C13 1.3597(18) . ?
N4 C14 1.4611(19) . ?
N4 C15 1.4408(18) . ?
C1 H1 0.9500 . ?
C1 C2 1.385(2) . ?
C1 C6 1.3959(19) . ?
C2 H2 0.9500 . ?
C2 C3 1.395(2) . ?
C3 C4 1.384(2) . ?
C3 C7 1.509(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.394(2) . ?
C5 H5 0.9500 . ?
C5 C6 1.386(2) . ?
C6 C8 1.5319(19) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C9 1.5299(19) . ?
C8 C11 1.5254(19) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C16 1.389(2) . ?
C15 C20 1.384(2) . ?
C16 H16 0.9500 . ?
C16 C17 1.388(2) . ?
C17 H17 0.9500 . ?
C17 C18 1.393(2) . ?
C18 C19 1.388(2) . ?
C18 C21 1.515(2) . ?
C19 H19 0.9500 . ?
C19 C20 1.393(2) . ?
C20 H20 0.9500 . ?
C21 H21A 0.9800 . ?
C21 H21B 0.9800 . ?
C21 H21C 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
C9 N1 C10 111.80(12) . . ?
C9 N1 C12 124.85(12) . . ?
C10 N1 C12 123.04(12) . . ?
N3 N2 C8 122.63(11) . . ?
C10 N2 N3 122.71(11) . . ?
C10 N2 C8 114.05(11) . . ?
N2 N3 C13 115.42(11) . . ?
N2 N3 H3 112.5(13) . . ?
C13 N3 H3 120.5(13) . . ?
C13 N4 C14 118.37(12) . . ?
C13 N4 C15 123.38(12) . . ?
C15 N4 C14 117.99(12) . . ?
C2 C1 H1 119.4 . . ?
C2 C1 C6 121.21(13) . . ?
C6 C1 H1 119.4 . . ?
C1 C2 H2 119.7 . . ?
C1 C2 C3 120.53(14) . . ?
C3 C2 H2 119.7 . . ?
C2 C3 C7 119.93(14) . . ?
C4 C3 C2 118.18(14) . . ?
C4 C3 C7 121.88(14) . . ?
C3 C4 H4 119.3 . . ?
C3 C4 C5 121.39(14) . . ?
C5 C4 H4 119.3 . . ?
C4 C5 H5 119.8 . . ?
C6 C5 C4 120.45(14) . . ?
C6 C5 H5 119.8 . . ?
C1 C6 C8 119.23(12) . . ?
C5 C6 C1 118.23(13) . . ?
C5 C6 C8 122.45(12) . . ?
C3 C7 H7A 109.5 . . ?
C3 C7 H7B 109.5 . . ?
C3 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N2 C8 C6 111.12(11) . . ?
N2 C8 C9 99.92(11) . . ?
N2 C8 C11 112.70(12) . . ?
C9 C8 C6 107.61(11) . . ?
C11 C8 C6 114.74(11) . . ?
C11 C8 C9 109.59(11) . . ?
O1 C9 N1 126.58(14) . . ?
O1 C9 C8 125.48(13) . . ?
N1 C9 C8 107.94(12) . . ?
O2 C10 N1 125.60(13) . . ?
O2 C10 N2 128.60(14) . . ?
N2 C10 N1 105.80(12) . . ?
C8 C11 H11A 109.5 . . ?
C8 C11 H11B 109.5 . . ?
C8 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N1 C12 H12A 109.5 . . ?
N1 C12 H12B 109.5 . . ?
N1 C12 H12C 109.5 . . ?
H12A C12 H12B 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
O3 C13 N3 122.12(13) . . ?
O3 C13 N4 123.75(13) . . ?
N4 C13 N3 114.08(12) . . ?
N4 C14 H14A 109.5 . . ?
N4 C14 H14B 109.5 . . ?
N4 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C16 C15 N4 120.07(13) . . ?
C20 C15 N4 120.25(13) . . ?
C20 C15 C16 119.66(13) . . ?
C15 C16 H16 120.0 . . ?
C17 C16 C15 119.96(14) . . ?
C17 C16 H16 120.0 . . ?
C16 C17 H17 119.5 . . ?
C16 C17 C18 120.91(14) . . ?
C18 C17 H17 119.5 . . ?
C17 C18 C21 120.45(14) . . ?
C19 C18 C17 118.54(14) . . ?
C19 C18 C21 121.00(14) . . ?
C18 C19 H19 119.6 . . ?
C18 C19 C20 120.81(14) . . ?
C20 C19 H19 119.6 . . ?
C15 C20 C19 120.09(14) . . ?
C15 C20 H20 120.0 . . ?
C19 C20 H20 120.0 . . ?
C18 C21 H21A 109.5 . . ?
C18 C21 H21B 109.5 . . ?
C18 C21 H21C 109.5 . . ?
H21A C21 H21B 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?

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
_geom_hbond_publ_flag
N3 H3 O1 0.857(19) 2.04(2) 2.8486(16) 155.9(18) 4_556 yes

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
N2 N3 C13 O3 16.6(2) . . . . ?
N2 N3 C13 N4 -165.86(12) . . . . ?
N2 C8 C9 O1 -174.24(13) . . . . ?
N2 C8 C9 N1 5.64(14) . . . . ?
N3 N2 C8 C6 -77.41(15) . . . . ?
N3 N2 C8 C9 169.21(11) . . . . ?
N3 N2 C8 C11 52.97(16) . . . . ?
N3 N2 C10 O2 7.4(2) . . . . ?
N3 N2 C10 N1 -173.38(11) . . . . ?
N4 C15 C16 C17 -179.81(14) . . . . ?
N4 C15 C20 C19 178.48(14) . . . . ?
C1 C2 C3 C4 -0.5(2) . . . . ?
C1 C2 C3 C7 -179.76(15) . . . . ?
C1 C6 C8 N2 -42.17(17) . . . . ?
C1 C6 C8 C9 66.27(15) . . . . ?
C1 C6 C8 C11 -171.48(12) . . . . ?
C2 C1 C6 C5 0.8(2) . . . . ?
C2 C1 C6 C8 -175.78(13) . . . . ?
C2 C3 C4 C5 1.0(2) . . . . ?
C3 C4 C5 C6 -0.6(2) . . . . ?
C4 C5 C6 C1 -0.3(2) . . . . ?
C4 C5 C6 C8 176.15(14) . . . . ?
C5 C6 C8 N2 141.39(13) . . . . ?
C5 C6 C8 C9 -110.17(15) . . . . ?
C5 C6 C8 C11 12.08(19) . . . . ?
C6 C1 C2 C3 -0.4(2) . . . . ?
C6 C8 C9 O1 69.71(17) . . . . ?
C6 C8 C9 N1 -110.42(12) . . . . ?
C7 C3 C4 C5 -179.77(16) . . . . ?
C8 N2 N3 C13 -105.42(14) . . . . ?
C8 N2 C10 O2 178.68(14) . . . . ?
C8 N2 C10 N1 -2.12(15) . . . . ?
C9 N1 C10 O2 -174.63(14) . . . . ?
C9 N1 C10 N2 6.14(15) . . . . ?
C10 N1 C9 O1 172.34(14) . . . . ?
C10 N1 C9 C8 -7.53(15) . . . . ?
C10 N2 N3 C13 65.09(17) . . . . ?
C10 N2 C8 C6 111.32(13) . . . . ?
C10 N2 C8 C9 -2.05(14) . . . . ?
C10 N2 C8 C11 -118.29(13) . . . . ?
C11 C8 C9 O1 -55.67(18) . . . . ?
C11 C8 C9 N1 124.20(13) . . . . ?
C12 N1 C9 O1 -1.4(2) . . . . ?
C12 N1 C9 C8 178.73(13) . . . . ?
C12 N1 C10 O2 -0.8(2) . . . . ?
C12 N1 C10 N2 -179.99(12) . . . . ?
C13 N4 C15 C16 -93.98(18) . . . . ?
C13 N4 C15 C20 87.89(18) . . . . ?
C14 N4 C13 O3 1.7(2) . . . . ?
C14 N4 C13 N3 -175.80(13) . . . . ?
C14 N4 C15 C16 80.10(18) . . . . ?
C14 N4 C15 C20 -98.04(17) . . . . ?
C15 N4 C13 O3 175.77(14) . . . . ?
C15 N4 C13 N3 -1.7(2) . . . . ?
C15 C16 C17 C18 1.5(2) . . . . ?
C16 C15 C20 C19 0.3(2) . . . . ?
C16 C17 C18 C19 -0.1(2) . . . . ?
C16 C17 C18 C21 -179.08(15) . . . . ?
C17 C18 C19 C20 -1.3(2) . . . . ?
C18 C19 C20 C15 1.1(2) . . . . ?
C20 C15 C16 C17 -1.7(2) . . . . ?
C21 C18 C19 C20 177.73(15) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_testm1_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1867366'
_audit_update_record             
;
2018-09-12 deposited with the CCDC.
2019-02-04 downloaded from the CCDC.
;
_audit_creation_date             2018-06-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H21 N3 O4'
_chemical_formula_sum            'C16 H21 N3 O4'
_chemical_formula_weight         319.36
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_cell_length_a                   21.1353(4)
_cell_length_b                   9.1587(2)
_cell_length_c                   16.9027(3)
_cell_angle_alpha                90
_cell_angle_beta                 92.2710(10)
_cell_angle_gamma                90
_cell_volume                     3269.32(11)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9982
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      27.82
_cell_measurement_theta_min      2.41
_shelx_estimated_absorpt_T_max   0.976
_shelx_estimated_absorpt_T_min   0.952
_exptl_absorpt_coefficient_mu    0.094
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6533
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0609 before and 0.0508 after correction. The Ratio of minimum to maximum transmission is 0.8762. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.298
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1360
_exptl_crystal_size_max          0.53
_exptl_crystal_size_mid          0.322
_exptl_crystal_size_min          0.261
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0451
_diffrn_reflns_av_unetI/netI     0.0272
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            58345
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.952
_diffrn_reflns_theta_min         1.929
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'Bruker area detector'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'CCD area detector'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'Bruker Apex II kappa CCD area detector'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6284
_reflns_number_total             7838
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.37A (Bruker, 2015)'
_computing_data_collection       'Bruker Apex suite'
_computing_data_reduction        'SAINT v8.37A (Bruker, 2015)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.341
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     433
_refine_ls_number_reflns         7838
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0511
_refine_ls_R_factor_gt           0.0376
_refine_ls_restrained_S_all      1.021
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0393P)²+1.1726P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0859
_refine_ls_wR_factor_ref         0.0932
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C6(H6), C7(H7), C8(H8), C9(H9), C10(H10), C22(H22), C23(H23), C24(H24),
 C25(H25), C26(H26)
2.b Idealised Me refined as rotating group:
 C4(H4A,H4B,H4C), C11(H11A,H11B,H11C), C14(H14A,H14B,H14C), C15(H15A,H15B,
 H15C), C16(H16A,H16B,H16C), C013(H01A,H01B,H01C), C20(H20A,H20B,H20C),
 C29(H29A,H29B,H29C), C30(H30A,H30B,H30C), C31(H31A,H31B,H31C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.95657(4) 0.86073(9) 0.58335(5) 0.01968(19) Uani 1 1 d . . . . .
O2 O 0.74679(4) 0.95550(10) 0.53168(6) 0.0234(2) Uani 1 1 d . . . . .
O3 O 0.94121(4) 0.66169(9) 0.42536(5) 0.0223(2) Uani 1 1 d . . . . .
O4 O 1.02578(4) 0.77490(9) 0.37184(5) 0.02006(19) Uani 1 1 d . . . . .
N1 N 0.84813(5) 0.90302(12) 0.57760(6) 0.0187(2) Uani 1 1 d . . . . .
N2 N 0.90125(4) 0.93135(11) 0.46892(6) 0.0148(2) Uani 1 1 d . . . . .
N3 N 0.94937(5) 0.91018(11) 0.41731(6) 0.0163(2) Uani 1 1 d . . . . .
C1 C 0.90816(6) 0.89409(12) 0.54670(7) 0.0157(2) Uani 1 1 d . . . . .
C2 C 0.80246(6) 0.93952(13) 0.52078(7) 0.0171(2) Uani 1 1 d . . . . .
C3 C 0.83535(5) 0.95550(13) 0.44172(7) 0.0154(2) Uani 1 1 d . . . . .
C4 C 0.83607(7) 0.88080(17) 0.66086(8) 0.0285(3) Uani 1 1 d . . . . .
H4A H 0.820096 0.781581 0.668598 0.043 Uiso 1 1 calc GR . . . .
H4B H 0.804503 0.951630 0.677552 0.043 Uiso 1 1 calc GR . . . .
H4C H 0.875484 0.894228 0.692543 0.043 Uiso 1 1 calc GR . . . .
C5 C 0.82494(6) 1.10937(13) 0.40959(7) 0.0151(2) Uani 1 1 d . . . . .
C6 C 0.76877(6) 1.14458(14) 0.36784(7) 0.0192(2) Uani 1 1 d . . . . .
H6 H 0.737554 1.071466 0.358005 0.023 Uiso 1 1 calc R . . . .
C7 C 0.75817(6) 1.28588(15) 0.34056(8) 0.0227(3) Uani 1 1 d . . . . .
H7 H 0.719882 1.308771 0.311905 0.027 Uiso 1 1 calc R . . . .
C8 C 0.80315(6) 1.39345(14) 0.35494(7) 0.0224(3) Uani 1 1 d . . . . .
H8 H 0.795775 1.489992 0.336202 0.027 Uiso 1 1 calc R . . . .
C9 C 0.85900(6) 1.35987(14) 0.39679(8) 0.0216(3) Uani 1 1 d . . . . .
H9 H 0.889884 1.433590 0.406948 0.026 Uiso 1 1 calc R . . . .
C10 C 0.86987(6) 1.21834(13) 0.42391(7) 0.0186(2) Uani 1 1 d . . . . .
H10 H 0.908264 1.195853 0.452446 0.022 Uiso 1 1 calc R . . . .
C11 C 0.81214(6) 0.83541(14) 0.38465(8) 0.0222(3) Uani 1 1 d . . . . .
H11A H 0.834245 0.843607 0.334960 0.033 Uiso 1 1 calc GR . . . .
H11B H 0.766471 0.846112 0.373931 0.033 Uiso 1 1 calc GR . . . .
H11C H 0.820858 0.739633 0.408529 0.033 Uiso 1 1 calc GR . . . .
C12 C 0.97027(6) 0.76873(13) 0.40680(7) 0.0162(2) Uani 1 1 d . . . . .
C13 C 1.05345(6) 0.64125(14) 0.33728(7) 0.0216(3) Uani 1 1 d . . . . .
C14 C 1.11162(7) 0.70215(18) 0.29951(9) 0.0341(3) Uani 1 1 d . . . . .
H14A H 1.098869 0.777867 0.261128 0.051 Uiso 1 1 calc GR . . . .
H14B H 1.133548 0.623508 0.272402 0.051 Uiso 1 1 calc GR . . . .
H14C H 1.140083 0.744511 0.340539 0.051 Uiso 1 1 calc GR . . . .
C15 C 1.00714(8) 0.5784(2) 0.27539(9) 0.0382(4) Uani 1 1 d . . . . .
H15A H 0.969342 0.543134 0.301186 0.057 Uiso 1 1 calc GR . . . .
H15B H 1.027158 0.497162 0.248144 0.057 Uiso 1 1 calc GR . . . .
H15C H 0.995017 0.654390 0.236877 0.057 Uiso 1 1 calc GR . . . .
C16 C 1.07128(7) 0.53285(16) 0.40193(8) 0.0295(3) Uani 1 1 d . . . . .
H16A H 1.099066 0.580277 0.441983 0.044 Uiso 1 1 calc GR . . . .
H16B H 1.093437 0.449875 0.379078 0.044 Uiso 1 1 calc GR . . . .
H16C H 1.032877 0.498179 0.426613 0.044 Uiso 1 1 calc GR . . . .
O5 O 0.49301(4) 0.74183(9) 0.46679(5) 0.02106(19) Uani 1 1 d . . . . .
O6 O 0.39188(4) 0.91432(10) 0.68170(6) 0.0260(2) Uani 1 1 d . . . . .
O7 O 0.61660(4) 0.70916(10) 0.59822(6) 0.0223(2) Uani 1 1 d . . . . .
O8 O 0.62880(4) 0.46681(9) 0.56952(5) 0.01881(18) Uani 1 1 d . . . . .
N4 N 0.43535(5) 0.85694(11) 0.56320(6) 0.0184(2) Uani 1 1 d . . . . .
N5 N 0.48853(5) 0.65689(11) 0.59531(6) 0.0171(2) Uani 1 1 d . . . . .
N6 N 0.53353(5) 0.54895(12) 0.59067(6) 0.0181(2) Uani 1 1 d . . . . .
C013 C 0.51094(6) 0.73814(15) 0.73343(8) 0.0232(3) Uani 1 1 d . . . . .
H01A H 0.533834 0.649572 0.750061 0.035 Uiso 1 1 calc GR . . . .
H01B H 0.490737 0.781273 0.779107 0.035 Uiso 1 1 calc GR . . . .
H01C H 0.540696 0.808446 0.711932 0.035 Uiso 1 1 calc GR . . . .
C17 C 0.47496(6) 0.74972(13) 0.53413(7) 0.0165(2) Uani 1 1 d . . . . .
C18 C 0.42452(6) 0.83708(13) 0.64197(7) 0.0188(2) Uani 1 1 d . . . . .
C19 C 0.46031(6) 0.69936(13) 0.66980(7) 0.0168(2) Uani 1 1 d . . . . .
C20 C 0.40844(6) 0.97633(14) 0.51556(8) 0.0237(3) Uani 1 1 d . . . . .
H20A H 0.423750 0.970118 0.461689 0.036 Uiso 1 1 calc GR . . . .
H20B H 0.421371 1.069883 0.539245 0.036 Uiso 1 1 calc GR . . . .
H20C H 0.362146 0.969128 0.513769 0.036 Uiso 1 1 calc GR . . . .
C21 C 0.41338(5) 0.58452(13) 0.69631(7) 0.0169(2) Uani 1 1 d . . . . .
C22 C 0.39242(6) 0.47418(14) 0.64487(8) 0.0207(3) Uani 1 1 d . . . . .
H22 H 0.407821 0.469656 0.592879 0.025 Uiso 1 1 calc R . . . .
C23 C 0.34921(6) 0.37087(15) 0.66909(8) 0.0235(3) Uani 1 1 d . . . . .
H23 H 0.335715 0.295034 0.633979 0.028 Uiso 1 1 calc R . . . .
C24 C 0.32581(6) 0.37808(14) 0.74401(8) 0.0238(3) Uani 1 1 d . . . . .
H24 H 0.295920 0.307764 0.760198 0.029 Uiso 1 1 calc R . . . .
C25 C 0.34578(6) 0.48749(15) 0.79569(8) 0.0232(3) Uani 1 1 d . . . . .
H25 H 0.329554 0.492251 0.847247 0.028 Uiso 1 1 calc R . . . .
C26 C 0.38954(6) 0.59033(14) 0.77218(7) 0.0199(3) Uani 1 1 d . . . . .
H26 H 0.403320 0.665007 0.807868 0.024 Uiso 1 1 calc R . . . .
C27 C 0.59631(6) 0.58791(13) 0.58737(7) 0.0168(2) Uani 1 1 d . . . . .
C28 C 0.69837(6) 0.46209(13) 0.58298(7) 0.0180(2) Uani 1 1 d . . . . .
C29 C 0.73070(6) 0.57271(15) 0.53159(8) 0.0251(3) Uani 1 1 d . . . . .
H29A H 0.717727 0.556520 0.475980 0.038 Uiso 1 1 calc GR . . . .
H29B H 0.776728 0.561667 0.538251 0.038 Uiso 1 1 calc GR . . . .
H29C H 0.718573 0.671507 0.547304 0.038 Uiso 1 1 calc GR . . . .
C30 C 0.71413(6) 0.30788(14) 0.55766(9) 0.0252(3) Uani 1 1 d . . . . .
H30A H 0.693319 0.237907 0.591962 0.038 Uiso 1 1 calc GR . . . .
H30B H 0.760070 0.293337 0.562005 0.038 Uiso 1 1 calc GR . . . .
H30C H 0.699166 0.292740 0.502652 0.038 Uiso 1 1 calc GR . . . .
C31 C 0.71346(7) 0.48406(16) 0.67073(8) 0.0281(3) Uani 1 1 d . . . . .
H31A H 0.701392 0.583136 0.686000 0.042 Uiso 1 1 calc GR . . . .
H31B H 0.758956 0.470282 0.681636 0.042 Uiso 1 1 calc GR . . . .
H31C H 0.689778 0.412936 0.701189 0.042 Uiso 1 1 calc GR . . . .
H3 H 0.9763(7) 0.9816(17) 0.4152(9) 0.024(4) Uiso 1 1 d . . . . .
H6A H 0.5222(8) 0.4594(19) 0.5764(10) 0.033(4) Uiso 1 1 d . . . . .


_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
O1 C1 1.2140(14) . ?
O2 C2 1.2071(15) . ?
O3 C12 1.2050(15) . ?
O4 C12 1.3354(14) . ?
O4 C13 1.4862(15) . ?
N1 C1 1.3935(15) . ?
N1 C2 1.3756(16) . ?
N1 C4 1.4545(16) . ?
N2 N3 1.3797(13) . ?
N2 C1 1.3604(15) . ?
N2 C3 1.4661(15) . ?
N3 C12 1.3825(15) . ?
C2 C3 1.5376(17) . ?
C3 C5 1.5231(16) . ?
C3 C11 1.5308(16) . ?
C5 C6 1.3947(16) . ?
C5 C10 1.3922(17) . ?
C6 C7 1.3890(18) . ?
C7 C8 1.3838(19) . ?
C8 C9 1.3865(18) . ?
C9 C10 1.3909(17) . ?
C13 C14 1.514(2) . ?
C13 C15 1.5173(19) . ?
C13 C16 1.5130(18) . ?
O5 C17 1.2169(15) . ?
O6 C18 1.2098(15) . ?
O7 C27 1.2019(15) . ?
O8 C27 1.3450(14) . ?
O8 C28 1.4796(14) . ?
N4 C17 1.3925(16) . ?
N4 C18 1.3720(16) . ?
N4 C20 1.4598(16) . ?
N5 N6 1.3762(14) . ?
N5 C17 1.3606(16) . ?
N5 C19 1.4669(15) . ?
N6 C27 1.3773(15) . ?
C013 C19 1.5286(17) . ?
C18 C19 1.5351(17) . ?
C19 C21 1.5251(17) . ?
C21 C22 1.3939(17) . ?
C21 C26 1.3974(17) . ?
C22 C23 1.3881(18) . ?
C23 C24 1.3793(19) . ?
C24 C25 1.384(2) . ?
C25 C26 1.3890(18) . ?
C28 C29 1.5149(18) . ?
C28 C30 1.5166(17) . ?
C28 C31 1.5180(18) . ?

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
C12 O4 C13 120.36(10) . . ?
C1 N1 C4 123.48(11) . . ?
C2 N1 C1 112.13(10) . . ?
C2 N1 C4 124.36(11) . . ?
N3 N2 C3 122.53(9) . . ?
C1 N2 N3 121.48(10) . . ?
C1 N2 C3 113.91(9) . . ?
N2 N3 C12 117.41(10) . . ?
O1 C1 N1 125.80(11) . . ?
O1 C1 N2 127.76(11) . . ?
N2 C1 N1 106.44(10) . . ?
O2 C2 N1 125.75(12) . . ?
O2 C2 C3 126.73(11) . . ?
N1 C2 C3 107.52(10) . . ?
N2 C3 C2 99.77(9) . . ?
N2 C3 C5 111.93(9) . . ?
N2 C3 C11 111.46(10) . . ?
C5 C3 C2 109.52(9) . . ?
C5 C3 C11 113.70(10) . . ?
C11 C3 C2 109.55(10) . . ?
C6 C5 C3 120.16(11) . . ?
C10 C5 C3 120.89(10) . . ?
C10 C5 C6 118.90(11) . . ?
C7 C6 C5 120.41(12) . . ?
C8 C7 C6 120.30(12) . . ?
C7 C8 C9 119.78(12) . . ?
C8 C9 C10 120.07(12) . . ?
C9 C10 C5 120.54(11) . . ?
O3 C12 O4 127.98(11) . . ?
O3 C12 N3 124.06(11) . . ?
O4 C12 N3 107.94(10) . . ?
O4 C13 C14 101.60(11) . . ?
O4 C13 C15 109.27(11) . . ?
O4 C13 C16 110.32(10) . . ?
C14 C13 C15 111.18(12) . . ?
C16 C13 C14 111.30(11) . . ?
C16 C13 C15 112.61(13) . . ?
C27 O8 C28 120.18(9) . . ?
C17 N4 C20 124.06(11) . . ?
C18 N4 C17 112.01(10) . . ?
C18 N4 C20 123.94(11) . . ?
N6 N5 C19 123.01(10) . . ?
C17 N5 N6 122.07(10) . . ?
C17 N5 C19 113.95(10) . . ?
N5 N6 C27 119.03(10) . . ?
O5 C17 N4 125.95(11) . . ?
O5 C17 N5 127.54(12) . . ?
N5 C17 N4 106.50(10) . . ?
O6 C18 N4 125.57(12) . . ?
O6 C18 C19 126.54(12) . . ?
N4 C18 C19 107.89(10) . . ?
N5 C19 C013 111.62(10) . . ?
N5 C19 C18 99.62(9) . . ?
N5 C19 C21 111.14(10) . . ?
C013 C19 C18 110.32(10) . . ?
C21 C19 C013 113.50(10) . . ?
C21 C19 C18 109.77(9) . . ?
C22 C21 C19 120.73(11) . . ?
C22 C21 C26 118.87(11) . . ?
C26 C21 C19 120.39(11) . . ?
C23 C22 C21 120.45(12) . . ?
C24 C23 C22 120.14(12) . . ?
C23 C24 C25 120.18(12) . . ?
C24 C25 C26 120.01(12) . . ?
C25 C26 C21 120.34(12) . . ?
O7 C27 O8 127.87(11) . . ?
O7 C27 N6 124.87(11) . . ?
O8 C27 N6 107.26(10) . . ?
O8 C28 C29 111.12(10) . . ?
O8 C28 C30 102.23(9) . . ?
O8 C28 C31 108.39(10) . . ?
C29 C28 C30 110.61(11) . . ?
C29 C28 C31 112.92(11) . . ?
C30 C28 C31 111.05(11) . . ?

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
_geom_hbond_publ_flag
N3 H3 O1 0.869(16) 2.024(16) 2.8907(13) 175.5(14) 3_776 yes
N6 H6A O5 0.886(17) 2.003(17) 2.8822(14) 171.6(16) 3_666 yes

_olex2_submission_special_instructions 'No special instructions were received'
