# Electronic Supplementary Material (ESI) for ChemComm.
# 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_mo_2016393_0ma
_database_code_depnum_ccdc_archive 'CCDC 1560784'
_audit_update_record             
;
2017-09-06 deposited with the CCDC.
2017-10-16 downloaded from the CCDC.
;
_audit_creation_date             2017-09-06
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2017.07.04 svn.r3439 for OlexSys, GUI svn.r5361)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H18 N2 O6, C6 H6 N2 O'
_chemical_formula_sum            'C23 H24 N4 O7'
_chemical_formula_weight         468.46
_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/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.9427(16)
_cell_length_b                   12.732(3)
_cell_length_c                   22.382(4)
_cell_angle_alpha                90
_cell_angle_beta                 90.080(5)
_cell_angle_gamma                90
_cell_volume                     2263.4(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2358
_cell_measurement_temperature    170
_cell_measurement_theta_max      24.05
_cell_measurement_theta_min      2.72
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6234
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.0795 before and 0.0552 after correction. The Ratio of minimum to maximum transmission is 0.8361. The λ/2 correction factor is 0.0015.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.375
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             984
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0516
_diffrn_reflns_av_unetI/netI     0.0637
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            16009
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.688
_diffrn_reflns_theta_min         1.820
_diffrn_ambient_temperature      170
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.992
_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                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2754
_reflns_number_total             5263
_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 v7.68A (Bruker, 2009)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_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         0.235
_refine_diff_density_min         -0.231
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.994
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     311
_refine_ls_number_reflns         5263
_refine_ls_number_restraints     7
_refine_ls_R_factor_all          0.1188
_refine_ls_R_factor_gt           0.0570
_refine_ls_restrained_S_all      0.994
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1057P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1563
_refine_ls_wR_factor_ref         0.2000
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Rigid bond restraints
 N2, C17
 with sigma for 1-2 distances of 0.005 and sigma for 1-3 distances of 0.005
3. Uiso/Uaniso restraints and constraints
N2 \\sim C17: within 2A with sigma of 0.04 and sigma for terminal atoms of 0.08
4.a Ternary CH refined with riding coordinates:
 C3(H3)
4.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C20(H20), C13(H13), C21(H21), C23(H23), C14(H14), C16(H16), C15(H15),
 C22(H22)
4.c X=CH2 refined with riding coordinates:
 N3(H3A,H3B)
4.d Idealised Me refined as rotating group:
 C6(H6A,H6B,H6C), C7(H7A,H7B,H7C), C9(H9A,H9B,H9C), C11(H11A,H11B,H11C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_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
O2 O 1.1105(2) 0.61399(14) 0.82333(8) 0.0571(5) Uani 1 1 d . . . . .
O4 O 1.0307(3) 0.13948(14) 0.77217(9) 0.0592(5) Uani 1 1 d . . . . .
O3 O 1.0715(3) 0.24068(15) 0.85216(8) 0.0671(6) Uani 1 1 d . . . . .
N1 N 0.8384(3) 0.40252(15) 0.68072(9) 0.0467(5) Uani 1 1 d . . . . .
H1 H 0.7720 0.3970 0.6494 0.056 Uiso 1 1 calc R . . . .
O7 O 0.6505(3) 0.38951(17) 0.56944(9) 0.0703(6) Uani 1 1 d . . . . .
O5 O 1.1082(3) 0.44630(19) 0.92234(9) 0.0716(6) Uani 1 1 d . . . . .
O1 O 1.0316(3) 0.69622(15) 0.73997(10) 0.0735(6) Uani 1 1 d . . . . .
N2 N 0.9961(4) 0.5118(2) 0.92445(10) 0.0604(7) Uani 1 1 d . U . . .
O6 O 1.0085(4) 0.59635(18) 0.95039(10) 0.0911(8) Uani 1 1 d . . . . .
C3 C 0.9655(3) 0.42463(17) 0.79757(10) 0.0381(5) Uani 1 1 d . . . . .
H3 H 1.0729 0.4279 0.8208 0.046 Uiso 1 1 calc R . . . .
N3 N 0.6928(3) 0.31435(19) 0.48051(12) 0.0655(7) Uani 1 1 d . . . . .
H3A H 0.8029 0.3174 0.4845 0.079 Uiso 1 1 calc R . . . .
H3B H 0.6483 0.2871 0.4480 0.079 Uiso 1 1 calc R . . . .
C2 C 0.9636(3) 0.51449(18) 0.75230(11) 0.0406(6) Uani 1 1 d . . . . .
C19 C 0.4094(3) 0.34251(18) 0.51260(11) 0.0418(6) Uani 1 1 d . . . . .
C12 C 0.8186(3) 0.43925(17) 0.84037(11) 0.0394(5) Uani 1 1 d . . . . .
C4 C 0.9567(3) 0.31974(18) 0.76555(11) 0.0407(6) Uani 1 1 d . . . . .
N4 N 0.0606(3) 0.3283(2) 0.50061(13) 0.0677(7) Uani 1 1 d . . . . .
C5 C 0.8850(3) 0.31176(18) 0.71054(11) 0.0415(6) Uani 1 1 d . . . . .
C1 C 0.8915(3) 0.50130(18) 0.69793(11) 0.0427(6) Uani 1 1 d . . . . .
C10 C 1.0236(3) 0.2318(2) 0.80095(12) 0.0451(6) Uani 1 1 d . . . . .
C8 C 1.0347(3) 0.6165(2) 0.76943(12) 0.0464(6) Uani 1 1 d . . . . .
C17 C 0.8306(3) 0.48767(19) 0.89601(11) 0.0459(6) Uani 1 1 d . U . . .
C20 C 0.3350(3) 0.27147(19) 0.47377(12) 0.0478(6) Uani 1 1 d . . . . .
H20 H 0.4028 0.2261 0.4502 0.057 Uiso 1 1 calc R . . . .
C18 C 0.5952(3) 0.3504(2) 0.52283(12) 0.0486(6) Uani 1 1 d . . . . .
C13 C 0.6562(3) 0.41266(19) 0.82144(12) 0.0486(6) Uani 1 1 d . . . . .
H13 H 0.6422 0.3783 0.7841 0.058 Uiso 1 1 calc R . . . .
C6 C 0.8471(4) 0.2156(2) 0.67440(13) 0.0561(7) Uani 1 1 d . . . . .
H6A H 0.7431 0.2266 0.6516 0.084 Uiso 1 1 calc GR . . . .
H6B H 0.8333 0.1553 0.7011 0.084 Uiso 1 1 calc GR . . . .
H6C H 0.9402 0.2021 0.6468 0.084 Uiso 1 1 calc GR . . . .
C7 C 0.8657(4) 0.5834(2) 0.65043(13) 0.0558(7) Uani 1 1 d . . . . .
H7A H 0.9751 0.6050 0.6344 0.084 Uiso 1 1 calc GR . . . .
H7B H 0.8085 0.6444 0.6678 0.084 Uiso 1 1 calc GR . . . .
H7C H 0.7965 0.5542 0.6181 0.084 Uiso 1 1 calc GR . . . .
C21 C 0.1625(3) 0.2671(2) 0.46965(14) 0.0579(7) Uani 1 1 d . . . . .
H21 H 0.1139 0.2174 0.4431 0.070 Uiso 1 1 calc R . . . .
C23 C 0.3039(4) 0.4069(2) 0.54423(13) 0.0576(7) Uani 1 1 d . . . . .
H23 H 0.3484 0.4575 0.5711 0.069 Uiso 1 1 calc R . . . .
C14 C 0.5164(4) 0.4348(2) 0.85523(15) 0.0602(8) Uani 1 1 d . . . . .
H14 H 0.4079 0.4141 0.8417 0.072 Uiso 1 1 calc R . . . .
C16 C 0.6925(4) 0.5131(2) 0.92973(14) 0.0607(8) Uani 1 1 d . . . . .
H16 H 0.7055 0.5482 0.9669 0.073 Uiso 1 1 calc R . . . .
C15 C 0.5340(4) 0.4871(2) 0.90883(15) 0.0648(8) Uani 1 1 d . . . . .
H15 H 0.4371 0.5052 0.9314 0.078 Uiso 1 1 calc R . . . .
C22 C 0.1345(4) 0.3974(3) 0.53661(16) 0.0724(9) Uani 1 1 d . . . . .
H22 H 0.0640 0.4435 0.5586 0.087 Uiso 1 1 calc R . . . .
C9 C 1.1794(4) 0.7120(2) 0.84480(15) 0.0703(9) Uani 1 1 d . . . . .
H9A H 1.2599 0.7394 0.8156 0.106 Uiso 1 1 calc GR . . . .
H9B H 1.2369 0.7001 0.8830 0.106 Uiso 1 1 calc GR . . . .
H9C H 1.0881 0.7628 0.8504 0.106 Uiso 1 1 calc GR . . . .
C11 C 1.0937(4) 0.0515(2) 0.80613(15) 0.0694(9) Uani 1 1 d . . . . .
H11A H 1.1059 -0.0095 0.7798 0.104 Uiso 1 1 calc GR . . . .
H11B H 1.0145 0.0347 0.8383 0.104 Uiso 1 1 calc GR . . . .
H11C H 1.2035 0.0695 0.8234 0.104 Uiso 1 1 calc GR . . . .


_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
O2 C8 1.348(3) . ?
O2 C9 1.444(3) . ?
O4 C10 1.342(3) . ?
O4 C11 1.443(3) . ?
O3 C10 1.212(3) . ?
N1 H1 0.8800 . ?
N1 C5 1.384(3) . ?
N1 C1 1.381(3) . ?
O7 C18 1.236(3) . ?
O5 N2 1.221(3) . ?
O1 C8 1.210(3) . ?
N2 O6 1.227(3) . ?
N2 C17 1.492(4) . ?
C3 H3 1.0000 . ?
C3 C2 1.528(3) . ?
C3 C12 1.522(3) . ?
C3 C4 1.517(3) . ?
N3 H3A 0.8800 . ?
N3 H3B 0.8800 . ?
N3 C18 1.308(4) . ?
C2 C1 1.355(4) . ?
C2 C8 1.467(3) . ?
C19 C20 1.386(3) . ?
C19 C18 1.497(4) . ?
C19 C23 1.370(4) . ?
C12 C17 1.393(3) . ?
C12 C13 1.399(3) . ?
C4 C5 1.360(3) . ?
C4 C10 1.470(3) . ?
N4 C21 1.321(4) . ?
N4 C22 1.329(4) . ?
C5 C6 1.497(3) . ?
C1 C7 1.505(3) . ?
C17 C16 1.371(4) . ?
C20 H20 0.9500 . ?
C20 C21 1.374(4) . ?
C13 H13 0.9500 . ?
C13 C14 1.374(4) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C21 H21 0.9500 . ?
C23 H23 0.9500 . ?
C23 C22 1.361(4) . ?
C14 H14 0.9500 . ?
C14 C15 1.379(4) . ?
C16 H16 0.9500 . ?
C16 C15 1.383(5) . ?
C15 H15 0.9500 . ?
C22 H22 0.9500 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 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
C8 O2 C9 116.5(2) . . ?
C10 O4 C11 116.3(2) . . ?
C5 N1 H1 118.5 . . ?
C1 N1 H1 118.5 . . ?
C1 N1 C5 123.0(2) . . ?
O5 N2 O6 124.0(3) . . ?
O5 N2 C17 119.0(2) . . ?
O6 N2 C17 116.9(3) . . ?
C2 C3 H3 108.8 . . ?
C12 C3 H3 108.8 . . ?
C12 C3 C2 108.59(18) . . ?
C4 C3 H3 108.8 . . ?
C4 C3 C2 110.20(19) . . ?
C4 C3 C12 111.72(19) . . ?
H3A N3 H3B 120.0 . . ?
C18 N3 H3A 120.0 . . ?
C18 N3 H3B 120.0 . . ?
C1 C2 C3 120.4(2) . . ?
C1 C2 C8 120.4(2) . . ?
C8 C2 C3 119.1(2) . . ?
C20 C19 C18 124.0(2) . . ?
C23 C19 C20 117.0(2) . . ?
C23 C19 C18 119.0(2) . . ?
C17 C12 C3 124.4(2) . . ?
C17 C12 C13 116.1(2) . . ?
C13 C12 C3 119.2(2) . . ?
C5 C4 C3 120.8(2) . . ?
C5 C4 C10 125.6(2) . . ?
C10 C4 C3 113.5(2) . . ?
C21 N4 C22 116.0(3) . . ?
N1 C5 C6 111.6(2) . . ?
C4 C5 N1 119.0(2) . . ?
C4 C5 C6 129.3(2) . . ?
N1 C1 C7 113.2(2) . . ?
C2 C1 N1 119.5(2) . . ?
C2 C1 C7 127.3(2) . . ?
O4 C10 C4 115.1(2) . . ?
O3 C10 O4 121.5(2) . . ?
O3 C10 C4 123.5(2) . . ?
O2 C8 C2 112.6(2) . . ?
O1 C8 O2 121.1(2) . . ?
O1 C8 C2 126.3(3) . . ?
C12 C17 N2 122.1(2) . . ?
C16 C17 N2 114.9(2) . . ?
C16 C17 C12 122.9(3) . . ?
C19 C20 H20 120.3 . . ?
C21 C20 C19 119.5(3) . . ?
C21 C20 H20 120.3 . . ?
O7 C18 N3 122.8(3) . . ?
O7 C18 C19 120.3(3) . . ?
N3 C18 C19 116.8(2) . . ?
C12 C13 H13 119.0 . . ?
C14 C13 C12 122.0(3) . . ?
C14 C13 H13 119.0 . . ?
C5 C6 H6A 109.5 . . ?
C5 C6 H6B 109.5 . . ?
C5 C6 H6C 109.5 . . ?
H6A C6 H6B 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C1 C7 H7A 109.5 . . ?
C1 C7 H7B 109.5 . . ?
C1 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
N4 C21 C20 123.6(3) . . ?
N4 C21 H21 118.2 . . ?
C20 C21 H21 118.2 . . ?
C19 C23 H23 120.4 . . ?
C22 C23 C19 119.1(3) . . ?
C22 C23 H23 120.4 . . ?
C13 C14 H14 120.1 . . ?
C13 C14 C15 119.8(3) . . ?
C15 C14 H14 120.1 . . ?
C17 C16 H16 120.5 . . ?
C17 C16 C15 119.0(3) . . ?
C15 C16 H16 120.5 . . ?
C14 C15 C16 120.1(3) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
N4 C22 C23 124.8(3) . . ?
N4 C22 H22 117.6 . . ?
C23 C22 H22 117.6 . . ?
O2 C9 H9A 109.5 . . ?
O2 C9 H9B 109.5 . . ?
O2 C9 H9C 109.5 . . ?
H9A C9 H9B 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
O4 C11 H11A 109.5 . . ?
O4 C11 H11B 109.5 . . ?
O4 C11 H11C 109.5 . . ?
H11A C11 H11B 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 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
O5 N2 C17 C12 -42.5(3) . . . . ?
O5 N2 C17 C16 135.2(3) . . . . ?
N2 C17 C16 C15 -175.6(2) . . . . ?
O6 N2 C17 C12 139.7(2) . . . . ?
O6 N2 C17 C16 -42.6(3) . . . . ?
C3 C2 C1 N1 -8.1(4) . . . . ?
C3 C2 C1 C7 174.4(2) . . . . ?
C3 C2 C8 O2 6.4(3) . . . . ?
C3 C2 C8 O1 -174.6(3) . . . . ?
C3 C12 C17 N2 -12.2(4) . . . . ?
C3 C12 C17 C16 170.3(2) . . . . ?
C3 C12 C13 C14 -172.6(2) . . . . ?
C3 C4 C5 N1 7.9(4) . . . . ?
C3 C4 C5 C6 -172.8(2) . . . . ?
C3 C4 C10 O4 -174.7(2) . . . . ?
C3 C4 C10 O3 4.4(4) . . . . ?
C2 C3 C12 C17 -96.0(3) . . . . ?
C2 C3 C12 C13 77.2(3) . . . . ?
C2 C3 C4 C5 -25.9(3) . . . . ?
C2 C3 C4 C10 157.1(2) . . . . ?
C19 C20 C21 N4 0.7(4) . . . . ?
C19 C23 C22 N4 0.8(5) . . . . ?
C12 C3 C2 C1 -96.7(3) . . . . ?
C12 C3 C2 C8 80.8(3) . . . . ?
C12 C3 C4 C5 95.0(3) . . . . ?
C12 C3 C4 C10 -82.1(2) . . . . ?
C12 C17 C16 C15 2.1(4) . . . . ?
C12 C13 C14 C15 1.7(4) . . . . ?
C4 C3 C2 C1 26.0(3) . . . . ?
C4 C3 C2 C8 -156.5(2) . . . . ?
C4 C3 C12 C17 142.2(2) . . . . ?
C4 C3 C12 C13 -44.5(3) . . . . ?
C5 N1 C1 C2 -13.6(4) . . . . ?
C5 N1 C1 C7 164.2(2) . . . . ?
C5 C4 C10 O4 8.4(4) . . . . ?
C5 C4 C10 O3 -172.5(3) . . . . ?
C1 N1 C5 C4 13.8(4) . . . . ?
C1 N1 C5 C6 -165.7(2) . . . . ?
C1 C2 C8 O2 -176.1(2) . . . . ?
C1 C2 C8 O1 2.9(4) . . . . ?
C10 C4 C5 N1 -175.4(2) . . . . ?
C10 C4 C5 C6 3.9(5) . . . . ?
C8 C2 C1 N1 174.4(2) . . . . ?
C8 C2 C1 C7 -3.1(4) . . . . ?
C17 C12 C13 C14 1.2(4) . . . . ?
C17 C16 C15 C14 1.0(4) . . . . ?
C20 C19 C18 O7 -157.4(3) . . . . ?
C20 C19 C18 N3 22.7(4) . . . . ?
C20 C19 C23 C22 0.7(4) . . . . ?
C18 C19 C20 C21 176.9(2) . . . . ?
C18 C19 C23 C22 -177.7(3) . . . . ?
C13 C12 C17 N2 174.4(2) . . . . ?
C13 C12 C17 C16 -3.1(4) . . . . ?
C13 C14 C15 C16 -2.8(4) . . . . ?
C21 N4 C22 C23 -1.5(5) . . . . ?
C23 C19 C20 C21 -1.3(4) . . . . ?
C23 C19 C18 O7 20.9(4) . . . . ?
C23 C19 C18 N3 -159.0(3) . . . . ?
C22 N4 C21 C20 0.8(4) . . . . ?
C9 O2 C8 O1 3.0(4) . . . . ?
C9 O2 C8 C2 -178.0(2) . . . . ?
C11 O4 C10 O3 1.7(4) . . . . ?
C11 O4 C10 C4 -179.2(2) . . . . ?

_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_mo_2016529_0m_4
_database_code_depnum_ccdc_archive 'CCDC 1560785'
_audit_update_record             
;
2017-07-07 deposited with the CCDC.
2017-10-16 downloaded from the CCDC.
;
_audit_creation_date             2017-03-02
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2017.02.23 svn.r3390 for OlexSys, GUI svn.r5320)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C17 H18 N2 O6, C6 H6 N2 O'
_chemical_formula_sum            'C23 H24 N4 O7'
_chemical_formula_weight         468.46
_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.5743(2)
_cell_length_b                   11.4918(4)
_cell_length_c                   13.8653(4)
_cell_angle_alpha                106.089(2)
_cell_angle_beta                 97.442(2)
_cell_angle_gamma                103.739(2)
_cell_volume                     1101.47(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5263
_cell_measurement_temperature    170
_cell_measurement_theta_max      26.51
_cell_measurement_theta_min      2.83
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_T_max  0.987
_exptl_absorpt_correction_T_min  0.977
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
 TWINABS-2012/1 (Bruker,2012) was used for absorption correction.
 
For component 1:
 wR2(int) was 0.0762 before and 0.0523 after correction.
 The Ratio of minimum to maximum transmission not present.
 The λ/2 correction factor is Not present
 
For component 2:
 wR2(int) was 0.0876 before and 0.0565 after correction.
 The Ratio of minimum to maximum transmission is 0.87.
 The λ/2 correction factor is Not present

Final HKLF 4 output contains 32893 reflections, Rint = 0.0635
 (13425 with I > 3sig(I), Rint = 0.0441)
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.412
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             492
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0
_diffrn_reflns_av_unetI/netI     0.0505
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       ?
_diffrn_reflns_limit_h_min       ?
_diffrn_reflns_limit_k_max       ?
_diffrn_reflns_limit_k_min       ?
_diffrn_reflns_limit_l_max       ?
_diffrn_reflns_limit_l_min       ?
_diffrn_reflns_number            5039
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         27.499
_diffrn_reflns_theta_min         1.563
_diffrn_ambient_temperature      170
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3430
_reflns_number_total             5039
_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       ?
_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         0.453
_refine_diff_density_min         -0.263
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     311
_refine_ls_number_reflns         5039
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0936
_refine_ls_R_factor_gt           0.0574
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0720P)²+0.3540P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1360
_refine_ls_wR_factor_ref         0.1507
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups, All N(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C7(H7)
2.b Aromatic/amide H refined with riding coordinates:
 N2(H2), C5(H5), C21(H21), C4(H4), C20(H20), C3(H3), C2(H2A), C22(H22), C23(H23)
2.c X=CH2 refined with riding coordinates:
 N4(H4A,H4B)
2.d Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C15(H15A,H15B,H15C), C17(H17A,H17B,H17C), C12(H12A,H12B,
 H12C)
;
_atom_sites_solution_hydrogens   geom
_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
O5 O 0.0983(2) 0.29143(14) 0.24521(11) 0.0288(4) Uani 1 1 d . . . . .
O4 O 0.2103(2) -0.13070(14) 0.44402(12) 0.0325(4) Uani 1 1 d . . . . .
O3 O 0.1200(2) -0.11770(14) 0.28851(11) 0.0298(4) Uani 1 1 d . . . . .
O7 O 0.7028(2) 0.62033(16) 0.21956(12) 0.0376(4) Uani 1 1 d . . . . .
O1 O -0.0306(2) 0.01441(16) 0.13726(13) 0.0389(4) Uani 1 1 d . . . . .
N1 N 0.1071(2) -0.01937(17) 0.12158(13) 0.0254(4) Uani 1 1 d . . . . .
O2 O 0.0998(2) -0.11755(17) 0.05533(13) 0.0453(5) Uani 1 1 d . . . . .
N2 N 0.2872(2) 0.25791(16) 0.56994(13) 0.0249(4) Uani 1 1 d . . . . .
H2 H 0.3287 0.2953 0.6364 0.030 Uiso 1 1 calc R . . . .
N4 N 0.9309(3) 0.63194(17) 0.12992(14) 0.0291(4) Uani 1 1 d . . . . .
H4A H 0.9971 0.7063 0.1730 0.035 Uiso 1 1 calc R . . . .
H4B H 0.9723 0.5957 0.0763 0.035 Uiso 1 1 calc R . . . .
N3 N 0.7353(3) 0.40506(18) -0.01280(14) 0.0289(4) Uani 1 1 d . . . . .
O6 O 0.1653(3) 0.46849(17) 0.37559(14) 0.0596(6) Uani 1 1 d . . . . .
C8 C 0.2085(3) 0.06973(19) 0.42965(15) 0.0189(4) Uani 1 1 d . . . . .
C6 C 0.3231(3) 0.13158(18) 0.28482(15) 0.0175(4) Uani 1 1 d . . . . .
C7 C 0.1787(3) 0.14061(18) 0.35269(15) 0.0179(4) Uani 1 1 d . . . . .
H7 H 0.0516 0.0992 0.3082 0.021 Uiso 1 1 calc R . . . .
C11 C 0.1746(3) -0.06620(19) 0.38077(15) 0.0200(4) Uani 1 1 d . . . . .
C9 C 0.2621(3) 0.12975(19) 0.53193(15) 0.0204(4) Uani 1 1 d . . . . .
C14 C 0.2517(3) 0.33148(19) 0.51061(16) 0.0231(5) Uani 1 1 d . . . . .
C13 C 0.1958(3) 0.27897(19) 0.40733(16) 0.0213(4) Uani 1 1 d . . . . .
C1 C 0.2919(3) 0.06048(19) 0.18202(16) 0.0211(4) Uani 1 1 d . . . . .
C16 C 0.1554(3) 0.3575(2) 0.34500(17) 0.0248(5) Uani 1 1 d . . . . .
C19 C 0.6617(3) 0.4488(2) 0.06855(16) 0.0243(5) Uani 1 1 d . . . . .
C18 C 0.7685(3) 0.5744(2) 0.14582(16) 0.0262(5) Uani 1 1 d . . . . .
C5 C 0.5080(3) 0.1967(2) 0.33258(17) 0.0244(5) Uani 1 1 d . . . . .
H5 H 0.5362 0.2442 0.4034 0.029 Uiso 1 1 calc R . . . .
C10 C 0.3007(3) 0.0736(2) 0.61579(16) 0.0296(5) Uani 1 1 d . . . . .
H10A H 0.4119 0.0447 0.6102 0.044 Uiso 1 1 calc GR . . . .
H10B H 0.1942 0.0018 0.6089 0.044 Uiso 1 1 calc GR . . . .
H10C H 0.3212 0.1378 0.6828 0.044 Uiso 1 1 calc GR . . . .
C21 C 0.3906(3) 0.2731(2) 0.00914(19) 0.0355(6) Uani 1 1 d . . . . .
H21 H 0.2739 0.2277 0.0170 0.043 Uiso 1 1 calc R . . . .
C4 C 0.6517(3) 0.1945(2) 0.28071(19) 0.0320(5) Uani 1 1 d . . . . .
H4 H 0.7758 0.2407 0.3157 0.038 Uiso 1 1 calc R . . . .
C20 C 0.4934(3) 0.3853(2) 0.08305(18) 0.0320(5) Uani 1 1 d . . . . .
H20 H 0.4491 0.4183 0.1429 0.038 Uiso 1 1 calc R . . . .
C15 C 0.2812(4) 0.4666(2) 0.57214(18) 0.0330(5) Uani 1 1 d . . . . .
H15A H 0.1632 0.4876 0.5640 0.050 Uiso 1 1 calc GR . . . .
H15B H 0.3726 0.5216 0.5480 0.050 Uiso 1 1 calc GR . . . .
H15C H 0.3271 0.4791 0.6447 0.050 Uiso 1 1 calc GR . . . .
C3 C 0.6148(3) 0.1250(2) 0.1779(2) 0.0351(6) Uani 1 1 d . . . . .
H3 H 0.7125 0.1247 0.1413 0.042 Uiso 1 1 calc R . . . .
C2 C 0.4351(3) 0.0563(2) 0.12906(18) 0.0315(5) Uani 1 1 d . . . . .
H2A H 0.4088 0.0058 0.0590 0.038 Uiso 1 1 calc R . . . .
C22 C 0.4597(3) 0.2283(2) -0.0760(2) 0.0373(6) Uani 1 1 d . . . . .
H22 H 0.3906 0.1524 -0.1289 0.045 Uiso 1 1 calc R . . . .
C23 C 0.6317(3) 0.2959(2) -0.08282(18) 0.0362(6) Uani 1 1 d . . . . .
H23 H 0.6799 0.2627 -0.1411 0.043 Uiso 1 1 calc R . . . .
C17 C 0.0422(4) 0.3593(2) 0.17946(19) 0.0367(6) Uani 1 1 d . . . . .
H17A H 0.0022 0.3028 0.1083 0.055 Uiso 1 1 calc GR . . . .
H17B H 0.1472 0.4311 0.1844 0.055 Uiso 1 1 calc GR . . . .
H17C H -0.0610 0.3904 0.2009 0.055 Uiso 1 1 calc GR . . . .
C12 C 0.1797(4) -0.2649(2) 0.39740(19) 0.0347(6) Uani 1 1 d . . . . .
H12A H 0.2700 -0.2788 0.3540 0.052 Uiso 1 1 calc GR . . . .
H12B H 0.0535 -0.3029 0.3553 0.052 Uiso 1 1 calc GR . . . .
H12C H 0.1948 -0.3041 0.4512 0.052 Uiso 1 1 calc GR . . . .


_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
O5 C16 1.336(3) . ?
O5 C17 1.440(3) . ?
O4 C11 1.336(2) . ?
O4 C12 1.446(3) . ?
O3 C11 1.219(2) . ?
O7 C18 1.237(3) . ?
O1 N1 1.220(2) . ?
N1 O2 1.226(2) . ?
N1 C1 1.471(3) . ?
N2 H2 0.8800 . ?
N2 C9 1.376(3) . ?
N2 C14 1.379(3) . ?
N4 H4A 0.8800 . ?
N4 H4B 0.8800 . ?
N4 C18 1.328(3) . ?
N3 C19 1.348(3) . ?
N3 C23 1.339(3) . ?
O6 C16 1.208(3) . ?
C8 C7 1.536(3) . ?
C8 C11 1.464(3) . ?
C8 C9 1.352(3) . ?
C6 C7 1.535(3) . ?
C6 C1 1.390(3) . ?
C6 C5 1.396(3) . ?
C7 H7 1.0000 . ?
C7 C13 1.526(3) . ?
C9 C10 1.507(3) . ?
C14 C13 1.355(3) . ?
C14 C15 1.497(3) . ?
C13 C16 1.466(3) . ?
C1 C2 1.389(3) . ?
C19 C18 1.500(3) . ?
C19 C20 1.380(3) . ?
C5 H5 0.9500 . ?
C5 C4 1.381(3) . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C10 H10C 0.9800 . ?
C21 H21 0.9500 . ?
C21 C20 1.379(3) . ?
C21 C22 1.372(4) . ?
C4 H4 0.9500 . ?
C4 C3 1.381(3) . ?
C20 H20 0.9500 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C3 H3 0.9500 . ?
C3 C2 1.374(3) . ?
C2 H2A 0.9500 . ?
C22 H22 0.9500 . ?
C22 C23 1.380(3) . ?
C23 H23 0.9500 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
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
C16 O5 C17 115.79(17) . . ?
C11 O4 C12 116.54(17) . . ?
O1 N1 O2 122.81(19) . . ?
O1 N1 C1 119.90(17) . . ?
O2 N1 C1 117.27(17) . . ?
C9 N2 H2 117.9 . . ?
C9 N2 C14 124.24(17) . . ?
C14 N2 H2 117.9 . . ?
H4A N4 H4B 120.0 . . ?
C18 N4 H4A 120.0 . . ?
C18 N4 H4B 120.0 . . ?
C23 N3 C19 115.9(2) . . ?
C11 C8 C7 113.30(16) . . ?
C9 C8 C7 122.08(18) . . ?
C9 C8 C11 124.62(18) . . ?
C1 C6 C7 127.32(17) . . ?
C1 C6 C5 115.91(18) . . ?
C5 C6 C7 116.68(18) . . ?
C8 C7 H7 108.8 . . ?
C6 C7 C8 108.83(15) . . ?
C6 C7 H7 108.8 . . ?
C13 C7 C8 111.44(16) . . ?
C13 C7 C6 110.01(16) . . ?
C13 C7 H7 108.8 . . ?
O4 C11 C8 115.50(17) . . ?
O3 C11 O4 121.76(18) . . ?
O3 C11 C8 122.73(18) . . ?
N2 C9 C10 112.22(18) . . ?
C8 C9 N2 119.83(18) . . ?
C8 C9 C10 127.95(19) . . ?
N2 C14 C15 113.20(18) . . ?
C13 C14 N2 119.89(19) . . ?
C13 C14 C15 126.9(2) . . ?
C14 C13 C7 122.06(19) . . ?
C14 C13 C16 119.52(19) . . ?
C16 C13 C7 118.39(18) . . ?
C6 C1 N1 123.06(17) . . ?
C2 C1 N1 114.64(18) . . ?
C2 C1 C6 122.27(19) . . ?
O5 C16 C13 112.26(18) . . ?
O6 C16 O5 120.8(2) . . ?
O6 C16 C13 126.9(2) . . ?
N3 C19 C18 117.59(19) . . ?
N3 C19 C20 123.5(2) . . ?
C20 C19 C18 118.9(2) . . ?
O7 C18 N4 123.1(2) . . ?
O7 C18 C19 119.8(2) . . ?
N4 C18 C19 117.14(19) . . ?
C6 C5 H5 118.8 . . ?
C4 C5 C6 122.5(2) . . ?
C4 C5 H5 118.8 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10B 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C20 C21 H21 120.6 . . ?
C22 C21 H21 120.6 . . ?
C22 C21 C20 118.9(2) . . ?
C5 C4 H4 120.0 . . ?
C3 C4 C5 119.9(2) . . ?
C3 C4 H4 120.0 . . ?
C19 C20 H20 120.6 . . ?
C21 C20 C19 118.8(2) . . ?
C21 C20 H20 120.6 . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C4 C3 H3 120.4 . . ?
C2 C3 C4 119.3(2) . . ?
C2 C3 H3 120.4 . . ?
C1 C2 H2A 120.0 . . ?
C3 C2 C1 120.1(2) . . ?
C3 C2 H2A 120.0 . . ?
C21 C22 H22 120.8 . . ?
C21 C22 C23 118.5(2) . . ?
C23 C22 H22 120.8 . . ?
N3 C23 C22 124.3(2) . . ?
N3 C23 H23 117.8 . . ?
C22 C23 H23 117.8 . . ?
O5 C17 H17A 109.5 . . ?
O5 C17 H17B 109.5 . . ?
O5 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O4 C12 H12A 109.5 . . ?
O4 C12 H12B 109.5 . . ?
O4 C12 H12C 109.5 . . ?
H12A C12 H12B 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
O1 N1 C1 C6 35.3(3) . . . . ?
O1 N1 C1 C2 -146.7(2) . . . . ?
N1 C1 C2 C3 -178.8(2) . . . . ?
O2 N1 C1 C6 -146.0(2) . . . . ?
O2 N1 C1 C2 32.0(3) . . . . ?
N2 C14 C13 C7 -2.8(3) . . . . ?
N2 C14 C13 C16 179.03(18) . . . . ?
N3 C19 C18 O7 177.24(19) . . . . ?
N3 C19 C18 N4 -1.9(3) . . . . ?
N3 C19 C20 C21 -2.3(3) . . . . ?
C8 C7 C13 C14 7.0(3) . . . . ?
C8 C7 C13 C16 -174.86(17) . . . . ?
C6 C7 C13 C14 -113.8(2) . . . . ?
C6 C7 C13 C16 64.3(2) . . . . ?
C6 C1 C2 C3 -0.7(3) . . . . ?
C6 C5 C4 C3 -0.7(3) . . . . ?
C7 C8 C11 O4 175.86(16) . . . . ?
C7 C8 C11 O3 -3.1(3) . . . . ?
C7 C8 C9 N2 1.5(3) . . . . ?
C7 C8 C9 C10 -178.47(19) . . . . ?
C7 C6 C1 N1 0.1(3) . . . . ?
C7 C6 C1 C2 -177.74(19) . . . . ?
C7 C6 C5 C4 178.84(19) . . . . ?
C7 C13 C16 O5 3.2(3) . . . . ?
C7 C13 C16 O6 -178.6(2) . . . . ?
C11 C8 C7 C6 -64.5(2) . . . . ?
C11 C8 C7 C13 174.06(16) . . . . ?
C11 C8 C9 N2 -178.92(17) . . . . ?
C11 C8 C9 C10 1.1(3) . . . . ?
C9 N2 C14 C13 -3.0(3) . . . . ?
C9 N2 C14 C15 176.89(19) . . . . ?
C9 C8 C7 C6 115.1(2) . . . . ?
C9 C8 C7 C13 -6.4(3) . . . . ?
C9 C8 C11 O4 -3.7(3) . . . . ?
C9 C8 C11 O3 177.31(19) . . . . ?
C14 N2 C9 C8 3.7(3) . . . . ?
C14 N2 C9 C10 -176.31(18) . . . . ?
C14 C13 C16 O5 -178.64(18) . . . . ?
C14 C13 C16 O6 -0.4(3) . . . . ?
C1 C6 C7 C8 108.1(2) . . . . ?
C1 C6 C7 C13 -129.6(2) . . . . ?
C1 C6 C5 C4 2.0(3) . . . . ?
C19 N3 C23 C22 -0.1(3) . . . . ?
C18 C19 C20 C21 176.5(2) . . . . ?
C5 C6 C7 C8 -68.3(2) . . . . ?
C5 C6 C7 C13 54.1(2) . . . . ?
C5 C6 C1 N1 176.52(18) . . . . ?
C5 C6 C1 C2 -1.3(3) . . . . ?
C5 C4 C3 C2 -1.5(4) . . . . ?
C21 C22 C23 N3 -1.8(4) . . . . ?
C4 C3 C2 C1 2.2(4) . . . . ?
C20 C19 C18 O7 -1.6(3) . . . . ?
C20 C19 C18 N4 179.22(19) . . . . ?
C20 C21 C22 C23 1.6(3) . . . . ?
C15 C14 C13 C7 177.26(19) . . . . ?
C15 C14 C13 C16 -0.9(3) . . . . ?
C22 C21 C20 C19 0.3(3) . . . . ?
C23 N3 C19 C18 -176.69(19) . . . . ?
C23 N3 C19 C20 2.1(3) . . . . ?
C17 O5 C16 O6 -2.9(3) . . . . ?
C17 O5 C16 C13 175.45(18) . . . . ?
C12 O4 C11 O3 -0.4(3) . . . . ?
C12 O4 C11 C8 -179.35(18) . . . . ?

_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_mo_2016560_0m
_database_code_depnum_ccdc_archive 'CCDC 1560787'
_audit_update_record             
;
2017-09-06 deposited with the CCDC.
2017-10-16 downloaded from the CCDC.
;
_audit_creation_date             2017-09-06
_audit_creation_method           
;
Olex2 1.2-beta
(compiled 2017.07.04 svn.r3439 for OlexSys, GUI svn.r5361)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C6 H6 N2 O, C17 H18 N2 O6'
_chemical_formula_sum            'C23 H24 N4 O7'
_chemical_formula_weight         468.46
_chemical_absolute_configuration .
_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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'

_cell_length_a                   7.8608(9)
_cell_length_b                   12.3313(14)
_cell_length_c                   22.699(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2200.3(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5093
_cell_measurement_temperature    170
_cell_measurement_theta_max      26.110
_cell_measurement_theta_min      2.742
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.5973
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.0894 before and 0.0589 after correction. The Ratio of minimum to maximum transmission is 0.8011. The λ/2 correction factor is 0.0015.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_colour_lustre     ?
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.414
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             984
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.12
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0435
_diffrn_reflns_av_unetI/netI     0.0445
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            18657
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.875
_diffrn_reflns_theta_min         1.794
_diffrn_ambient_temperature      170
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.990
_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                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.758
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.992
_reflns_number_gt                4395
_reflns_number_total             5183
_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 v7.68A (Bruker, 2009)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_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    'SIR2004 (Burla et al., 2007)'
_refine_diff_density_max         0.251
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.062
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   -0.2(12)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.011
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     344
_refine_ls_number_reflns         5183
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0518
_refine_ls_R_factor_gt           0.0399
_refine_ls_restrained_S_all      1.012
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0616P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0962
_refine_ls_wR_factor_ref         0.1026
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 1.2(12)
 -0.2(12)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, H1 of N1
 At 1.5 times of:
  All C(H,H) groups, H3A of N3, All C(H,H,H) groups
3. Restrained distances
 C6-H6A
 0.85 with sigma of 0.01
 C6-H6B
 0.85 with sigma of 0.01
 H6A-H6B
 1.388291 with sigma of 0.03
 C7-C5 \\sim C6-C1
 with sigma of 0.02
4.a Aromatic/amide H refined with riding coordinates:
 C9(H9), N1(H1), C20(H20), C21(H21), C12(H12)
4.b Idealised Me refined as rotating group:
 C7(H7A,H7B,H7C), C15(H15A,H15B,H15C), C17(H17A,H17B,H17C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_special_details      
;
The structure was solved using Direct Methods (ShelXS). RE = 0.1, Nqual =  -1, Ralpha = 0.039
;
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
N3 N 0.4803(3) 0.93950(19) 0.52384(10) 0.0252(5) Uani 1 1 d . . . . .
H3A H 0.361(4) 0.935(3) 0.5174(14) 0.038 Uiso 1 1 d R . . . .
N4 N 1.1162(2) 0.91606(17) 0.50668(9) 0.0248(5) Uani 1 1 d . . . . .
O7 O 0.5167(2) 0.86883(16) 0.43315(8) 0.0289(4) Uani 1 1 d . . . . .
C9 C 0.4145(3) 0.8409(2) 0.17944(12) 0.0246(5) Uani 1 1 d . . . . .
H9 H 0.4126 0.8771 0.2164 0.030 Uiso 1 1 calc R . . . .
O3 O 0.8473(2) 0.61345(15) 0.16789(8) 0.0321(4) Uani 1 1 d . . . . .
O4 O 0.7803(3) 0.53072(16) 0.25204(9) 0.0399(5) Uani 1 1 d . . . . .
O1 O 0.8398(2) 0.77726(16) 0.07085(8) 0.0324(4) Uani 1 1 d . . . . .
O2 O 0.7099(3) 0.63004(18) 0.04501(9) 0.0444(5) Uani 1 1 d . . . . .
N1 N 0.6254(3) 0.84165(17) 0.31344(9) 0.0251(4) Uani 1 1 d . . . . .
H1 H 0.5655 0.8499 0.3459 0.030 Uiso 1 1 calc R . . . .
O5 O 0.8708(3) 0.99913(15) 0.14403(8) 0.0329(4) Uani 1 1 d . . . . .
O6 O 0.7890(3) 1.11100(15) 0.21618(9) 0.0353(5) Uani 1 1 d . . . . .
C18 C 0.5764(3) 0.90576(19) 0.47951(11) 0.0206(5) Uani 1 1 d . . . . .
C23 C 0.8395(3) 0.9894(2) 0.52498(12) 0.0256(5) Uani 1 1 d . . . . .
H23 H 0.767(4) 1.042(2) 0.5473(13) 0.031 Uiso 1 1 d R . . . .
C22 C 1.0139(3) 0.9880(2) 0.53237(12) 0.0272(5) Uani 1 1 d . . . . .
H22 H 1.073(4) 1.041(2) 0.5555(14) 0.033 Uiso 1 1 d R . . . .
C11 C 0.2601(4) 0.7702(2) 0.09646(12) 0.0338(6) Uani 1 1 d . . . . .
H11 H 0.152(4) 0.764(2) 0.0756(15) 0.041 Uiso 1 1 d R . . . .
C10 C 0.2626(3) 0.8258(2) 0.14943(12) 0.0309(6) Uani 1 1 d . . . . .
H10 H 0.157(4) 0.852(2) 0.1664(13) 0.037 Uiso 1 1 d R . . . .
C3 C 0.7307(3) 0.81376(19) 0.19611(10) 0.0198(5) Uani 1 1 d . . . . .
N2 N 0.7152(3) 0.71659(18) 0.07124(9) 0.0279(5) Uani 1 1 d . . . . .
C5 C 0.6746(3) 0.9335(2) 0.28289(11) 0.0231(5) Uani 1 1 d D . . . .
C1 C 0.6655(3) 0.7379(2) 0.29567(11) 0.0227(5) Uani 1 1 d D . . . .
C6 C 0.6342(4) 0.6537(2) 0.34192(12) 0.0293(6) Uani 1 1 d D . . . .
H6A H 0.729(3) 0.622(2) 0.3529(13) 0.044 Uiso 1 1 d DR . . . .
H6B H 0.568(3) 0.6016(19) 0.3298(14) 0.044 Uiso 1 1 d DR . . . .
C7 C 0.6505(4) 1.0359(2) 0.31801(12) 0.0330(6) Uani 1 1 d D . . . .
H7A H 0.5972 1.0184 0.3559 0.049 Uiso 1 1 calc GR . . . .
H7B H 0.5772 1.0860 0.2961 0.049 Uiso 1 1 calc GR . . . .
H7C H 0.7612 1.0701 0.3250 0.049 Uiso 1 1 calc GR . . . .
C19 C 0.7650(3) 0.91240(19) 0.48820(10) 0.0203(5) Uani 1 1 d . . . . .
C20 C 0.8713(3) 0.8388(2) 0.46017(11) 0.0238(5) Uani 1 1 d . . . . .
H20 H 0.8257 0.7859 0.4342 0.029 Uiso 1 1 calc R . . . .
C21 C 1.0444(3) 0.8436(2) 0.47068(11) 0.0249(5) Uani 1 1 d . . . . .
H21 H 1.1160 0.7928 0.4513 0.030 Uiso 1 1 calc R . . . .
C8 C 0.5702(3) 0.80467(18) 0.15728(10) 0.0203(5) Uani 1 1 d . . . . .
C2 C 0.7290(3) 0.72151(19) 0.24077(10) 0.0200(5) Uani 1 1 d . . . . .
C14 C 0.7855(3) 0.6130(2) 0.22294(11) 0.0243(5) Uani 1 1 d . . . . .
C15 C 0.8972(4) 0.5088(2) 0.14456(14) 0.0396(7) Uani 1 1 d . . . . .
H15A H 0.9718 0.4721 0.1729 0.059 Uiso 1 1 calc GR . . . .
H15B H 0.9581 0.5190 0.1073 0.059 Uiso 1 1 calc GR . . . .
H15C H 0.7956 0.4645 0.1378 0.059 Uiso 1 1 calc GR . . . .
C12 C 0.4100(3) 0.7325(2) 0.07324(12) 0.0295(6) Uani 1 1 d . . . . .
H12 H 0.4103 0.6934 0.0372 0.035 Uiso 1 1 calc R . . . .
C13 C 0.5620(3) 0.7520(2) 0.10302(11) 0.0231(5) Uani 1 1 d . . . . .
C4 C 0.7368(3) 0.92285(19) 0.22762(10) 0.0204(5) Uani 1 1 d . . . . .
C16 C 0.8056(3) 1.0120(2) 0.19204(11) 0.0231(5) Uani 1 1 d . . . . .
C17 C 0.8452(4) 1.2011(2) 0.18109(15) 0.0418(7) Uani 1 1 d . . . . .
H17A H 0.9644 1.1905 0.1699 0.063 Uiso 1 1 calc GR . . . .
H17B H 0.8343 1.2682 0.2039 0.063 Uiso 1 1 calc GR . . . .
H17C H 0.7751 1.2062 0.1455 0.063 Uiso 1 1 calc GR . . . .
H6C H 0.575(4) 0.695(3) 0.3750(15) 0.044(9) Uiso 1 1 d . . . . .
H3B H 0.534(4) 0.960(3) 0.5558(17) 0.048(10) Uiso 1 1 d . . . . .
H3 H 0.840(4) 0.805(2) 0.1696(12) 0.028(7) 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
N3 H3A 0.95(3) . ?
N3 C18 1.325(3) . ?
N3 H3B 0.88(4) . ?
N4 C22 1.331(3) . ?
N4 C21 1.335(3) . ?
O7 C18 1.239(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.387(4) . ?
C9 C8 1.396(3) . ?
O3 C14 1.341(3) . ?
O3 C15 1.449(3) . ?
O4 C14 1.211(3) . ?
O1 N2 1.232(3) . ?
O2 N2 1.223(3) . ?
N1 H1 0.8800 . ?
N1 C5 1.383(3) . ?
N1 C1 1.378(3) . ?
O5 C16 1.214(3) . ?
O6 C16 1.345(3) . ?
O6 C17 1.437(3) . ?
C18 C19 1.498(3) . ?
C23 H23 1.00(3) . ?
C23 C22 1.381(4) . ?
C23 C19 1.393(3) . ?
C22 H22 0.96(3) . ?
C11 H11 0.98(3) . ?
C11 C10 1.384(4) . ?
C11 C12 1.372(4) . ?
C10 H10 0.97(3) . ?
C3 C8 1.543(3) . ?
C3 C2 1.524(3) . ?
C3 C4 1.524(3) . ?
C3 H3 1.05(3) . ?
N2 C13 1.470(3) . ?
C5 C7 1.506(4) . ?
C5 C4 1.353(3) . ?
C1 C6 1.497(3) . ?
C1 C2 1.357(3) . ?
C6 H6A 0.876(13) . ?
C6 H6B 0.869(13) . ?
C6 H6C 1.02(3) . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C19 C20 1.388(3) . ?
C20 H20 0.9500 . ?
C20 C21 1.383(3) . ?
C21 H21 0.9500 . ?
C8 C13 1.394(3) . ?
C2 C14 1.466(3) . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C12 H12 0.9500 . ?
C12 C13 1.393(3) . ?
C4 C16 1.467(3) . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 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
H3A N3 H3B 128(3) . . ?
C18 N3 H3A 115(2) . . ?
C18 N3 H3B 116(2) . . ?
C22 N4 C21 117.3(2) . . ?
C10 C9 H9 118.8 . . ?
C10 C9 C8 122.3(2) . . ?
C8 C9 H9 118.8 . . ?
C14 O3 C15 115.8(2) . . ?
C5 N1 H1 118.3 . . ?
C1 N1 H1 118.3 . . ?
C1 N1 C5 123.3(2) . . ?
C16 O6 C17 116.5(2) . . ?
N3 C18 C19 116.6(2) . . ?
O7 C18 N3 123.0(2) . . ?
O7 C18 C19 120.5(2) . . ?
C22 C23 H23 120.7(17) . . ?
C22 C23 C19 118.8(2) . . ?
C19 C23 H23 120.5(17) . . ?
N4 C22 C23 123.7(3) . . ?
N4 C22 H22 113.8(18) . . ?
C23 C22 H22 122.5(18) . . ?
C10 C11 H11 118.3(19) . . ?
C12 C11 H11 122.3(19) . . ?
C12 C11 C10 119.3(2) . . ?
C9 C10 H10 120.0(18) . . ?
C11 C10 C9 120.4(2) . . ?
C11 C10 H10 119.6(18) . . ?
C8 C3 H3 109.4(15) . . ?
C2 C3 C8 108.59(19) . . ?
C2 C3 C4 110.29(18) . . ?
C2 C3 H3 108.0(15) . . ?
C4 C3 C8 110.97(18) . . ?
C4 C3 H3 109.5(16) . . ?
O1 N2 C13 118.3(2) . . ?
O2 N2 O1 123.6(2) . . ?
O2 N2 C13 118.1(2) . . ?
N1 C5 C7 112.7(2) . . ?
C4 C5 N1 119.1(2) . . ?
C4 C5 C7 128.2(2) . . ?
N1 C1 C6 113.6(2) . . ?
C2 C1 N1 119.4(2) . . ?
C2 C1 C6 127.0(2) . . ?
C1 C6 H6A 112(2) . . ?
C1 C6 H6B 113(2) . . ?
C1 C6 H6C 103.9(18) . . ?
H6A C6 H6B 106(3) . . ?
H6A C6 H6C 114(3) . . ?
H6B C6 H6C 110(3) . . ?
C5 C7 H7A 109.5 . . ?
C5 C7 H7B 109.5 . . ?
C5 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C23 C19 C18 122.1(2) . . ?
C20 C19 C18 120.0(2) . . ?
C20 C19 C23 117.9(2) . . ?
C19 C20 H20 120.5 . . ?
C21 C20 C19 119.0(2) . . ?
C21 C20 H20 120.5 . . ?
N4 C21 C20 123.4(2) . . ?
N4 C21 H21 118.3 . . ?
C20 C21 H21 118.3 . . ?
C9 C8 C3 119.2(2) . . ?
C13 C8 C9 115.3(2) . . ?
C13 C8 C3 125.2(2) . . ?
C1 C2 C3 120.2(2) . . ?
C1 C2 C14 120.0(2) . . ?
C14 C2 C3 119.7(2) . . ?
O3 C14 C2 111.3(2) . . ?
O4 C14 O3 121.6(2) . . ?
O4 C14 C2 127.1(2) . . ?
O3 C15 H15A 109.5 . . ?
O3 C15 H15B 109.5 . . ?
O3 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C11 C12 H12 120.3 . . ?
C11 C12 C13 119.4(2) . . ?
C13 C12 H12 120.3 . . ?
C8 C13 N2 122.3(2) . . ?
C8 C13 C12 123.3(2) . . ?
C12 C13 N2 114.4(2) . . ?
C5 C4 C3 120.6(2) . . ?
C5 C4 C16 124.8(2) . . ?
C16 C4 C3 114.5(2) . . ?
O5 C16 O6 121.7(2) . . ?
O5 C16 C4 123.5(2) . . ?
O6 C16 C4 114.8(2) . . ?
O6 C17 H17A 109.5 . . ?
O6 C17 H17B 109.5 . . ?
O6 C17 H17C 109.5 . . ?
H17A C17 H17B 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 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
N3 C18 C19 C23 -28.2(3) . . . . ?
N3 C18 C19 C20 150.3(2) . . . . ?
O7 C18 C19 C23 152.8(2) . . . . ?
O7 C18 C19 C20 -28.7(3) . . . . ?
C9 C8 C13 N2 175.0(2) . . . . ?
C9 C8 C13 C12 -2.3(3) . . . . ?
O1 N2 C13 C8 -40.5(3) . . . . ?
O1 N2 C13 C12 137.0(2) . . . . ?
O2 N2 C13 C8 141.9(2) . . . . ?
O2 N2 C13 C12 -40.6(3) . . . . ?
N1 C5 C4 C3 8.3(3) . . . . ?
N1 C5 C4 C16 -175.1(2) . . . . ?
N1 C1 C2 C3 -9.3(3) . . . . ?
N1 C1 C2 C14 174.9(2) . . . . ?
C18 C19 C20 C21 -177.4(2) . . . . ?
C23 C19 C20 C21 1.2(3) . . . . ?
C22 N4 C21 C20 -1.4(4) . . . . ?
C22 C23 C19 C18 177.7(2) . . . . ?
C22 C23 C19 C20 -0.8(4) . . . . ?
C11 C12 C13 N2 -174.7(2) . . . . ?
C11 C12 C13 C8 2.8(4) . . . . ?
C10 C9 C8 C3 -173.6(2) . . . . ?
C10 C9 C8 C13 -0.2(3) . . . . ?
C10 C11 C12 C13 -0.8(4) . . . . ?
C3 C8 C13 N2 -12.0(4) . . . . ?
C3 C8 C13 C12 170.7(2) . . . . ?
C3 C2 C14 O3 5.5(3) . . . . ?
C3 C2 C14 O4 -174.5(2) . . . . ?
C3 C4 C16 O5 -8.1(3) . . . . ?
C3 C4 C16 O6 170.85(19) . . . . ?
C5 N1 C1 C6 166.8(2) . . . . ?
C5 N1 C1 C2 -12.4(3) . . . . ?
C5 C4 C16 O5 175.0(2) . . . . ?
C5 C4 C16 O6 -6.0(3) . . . . ?
C1 N1 C5 C7 -166.9(2) . . . . ?
C1 N1 C5 C4 12.9(4) . . . . ?
C1 C2 C14 O3 -178.7(2) . . . . ?
C1 C2 C14 O4 1.3(4) . . . . ?
C6 C1 C2 C3 171.7(2) . . . . ?
C6 C1 C2 C14 -4.1(4) . . . . ?
C7 C5 C4 C3 -172.0(2) . . . . ?
C7 C5 C4 C16 4.6(4) . . . . ?
C19 C23 C22 N4 -0.7(4) . . . . ?
C19 C20 C21 N4 -0.1(4) . . . . ?
C21 N4 C22 C23 1.8(4) . . . . ?
C8 C9 C10 C11 2.1(4) . . . . ?
C8 C3 C2 C1 -95.2(2) . . . . ?
C8 C3 C2 C14 80.6(2) . . . . ?
C8 C3 C4 C5 94.2(3) . . . . ?
C8 C3 C4 C16 -82.8(2) . . . . ?
C2 C3 C8 C9 78.6(3) . . . . ?
C2 C3 C8 C13 -94.2(3) . . . . ?
C2 C3 C4 C5 -26.2(3) . . . . ?
C2 C3 C4 C16 156.8(2) . . . . ?
C15 O3 C14 O4 3.6(4) . . . . ?
C15 O3 C14 C2 -176.4(2) . . . . ?
C12 C11 C10 C9 -1.6(4) . . . . ?
C4 C3 C8 C9 -42.8(3) . . . . ?
C4 C3 C8 C13 144.5(2) . . . . ?
C4 C3 C2 C1 26.6(3) . . . . ?
C4 C3 C2 C14 -157.6(2) . . . . ?
C17 O6 C16 O5 2.7(4) . . . . ?
C17 O6 C16 C4 -176.2(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 1.2(12)
2 -0.2(12)

