# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2018

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

data_jmv1am
_database_code_depnum_ccdc_archive 'CCDC 1574187'
_audit_update_record             
;
2018-03-25 deposited with the CCDC.
2018-05-08 downloaded from the CCDC.
;
_audit_creation_date             2017-10-09
_audit_creation_method           
;
Olex2 1.2-ac3
(compiled 2016.03.30 svn.r3266 for Rigaku Oxford Diffraction, GUI svn.r5168)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C12 H12 N2, 2(C5 H3 N2 O4)'
_chemical_formula_sum            'C22 H18 N6 O8'
_chemical_formula_weight         494.42
_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                   4.8211(14)
_cell_length_b                   9.065(3)
_cell_length_c                   12.470(4)
_cell_angle_alpha                74.963(6)
_cell_angle_beta                 88.260(6)
_cell_angle_gamma                89.779(6)
_cell_volume                     526.1(3)
_cell_formula_units_Z            1
_cell_measurement_reflns_used    881
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      23.16
_cell_measurement_theta_min      2.33
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.122
_exptl_absorpt_correction_T_max  .93
_exptl_absorpt_correction_T_min  0.853708
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS v.2.03 (Bruker,200?) was used for absorption correction.
R(int) was 0.0470 before and 0.0329 after correction.
The Ratio of minimum to maximum transmission is 0.8537.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.561
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             256
_exptl_crystal_size_max          .38
_exptl_crystal_size_mid          .22
_exptl_crystal_size_min          .14
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0483
_diffrn_reflns_av_unetI/netI     0.0605
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            5141
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         2.326
_diffrn_ambient_temperature      298
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1425
_reflns_number_total             1856
_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 v6.28A (Bruker, 2002)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v6.28A (Bruker, 2002)'
_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    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.280
_refine_diff_density_min         -0.315
_refine_diff_density_rms         0.062
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.199
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         1856
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1169
_refine_ls_R_factor_gt           0.0863
_refine_ls_restrained_S_all      1.199
_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)+(0.0637P)²+0.5143P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1747
_refine_ls_wR_factor_ref         0.1891
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N3(H3), N4(H4), N1(H1), C3(H3A), C11(H11), C8(H8), C9(H9), C10(H10), C7(H7)
;
_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
N3 N 0.2302(6) 0.8333(3) 0.5368(3) 0.0313(8) Uani 1 1 d . . . . .
H3 H 0.100778 0.872828 0.492465 0.038 Uiso 1 1 calc R . . . .
O3 O 0.9477(6) 0.5080(3) 0.7251(2) 0.0438(8) Uani 1 1 d . . . . .
O1 O 0.1779(6) 1.0277(3) 0.6187(3) 0.0453(9) Uani 1 1 d . . . . .
N4 N 0.5525(6) 0.6418(4) 0.5950(3) 0.0303(8) Uani 1 1 d . . . . .
H4 H 0.636744 0.560401 0.588939 0.036 Uiso 1 1 calc R . . . .
O2 O 0.2767(6) 0.6442(3) 0.4486(2) 0.0453(9) Uani 1 1 d . . . . .
N1 N 0.3207(6) 0.3426(4) 0.8341(3) 0.0298(8) Uani 1 1 d . . . . .
H1 H 0.192514 0.400824 0.799848 0.036 Uiso 1 1 calc R . . . .
O4 O 0.9177(7) 0.6698(4) 0.8324(3) 0.0521(9) Uani 1 1 d . . . . .
C1 C 0.8517(8) 0.6223(5) 0.7541(3) 0.0310(10) Uani 1 1 d . . . . .
C3 C 0.5063(8) 0.8352(4) 0.6884(3) 0.0336(10) Uani 1 1 d . . . . .
H3A H 0.559665 0.877651 0.744965 0.040 Uiso 1 1 calc R . . . .
C2 C 0.6277(8) 0.7071(4) 0.6777(3) 0.0260(9) Uani 1 1 d . . . . .
C6 C 0.7303(8) 0.1573(4) 0.9448(3) 0.0333(10) Uani 1 1 d . . . . .
C4 C 0.3494(8) 0.7006(4) 0.5218(3) 0.0285(9) Uani 1 1 d . . . . .
C11 C 0.9393(8) 0.0582(5) 1.0125(4) 0.0381(11) Uani 1 1 d . . . . .
H11 H 0.988330 0.080409 1.078170 0.046 Uiso 1 1 calc R . . . .
C8 C 0.3902(8) 0.3513(5) 0.9337(3) 0.0354(10) Uani 1 1 d . . . . .
H8 H 0.298676 0.420509 0.965767 0.043 Uiso 1 1 calc R . . . .
C9 C 0.6563(8) 0.1504(5) 0.8398(4) 0.0387(11) Uani 1 1 d . . . . .
H9 H 0.746001 0.083009 0.805471 0.046 Uiso 1 1 calc R . . . .
C10 C 0.4479(9) 0.2442(5) 0.7861(3) 0.0369(11) Uani 1 1 d . . . . .
H10 H 0.396267 0.238550 0.715998 0.044 Uiso 1 1 calc R . . . .
C5 C 0.2969(8) 0.9086(4) 0.6151(3) 0.0308(10) Uani 1 1 d . . . . .
C7 C 0.5931(8) 0.2615(5) 0.9912(3) 0.0355(10) Uani 1 1 d . . . . .
H7 H 0.638866 0.270220 1.061224 0.043 Uiso 1 1 calc R . . . .


_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 H3 0.8600 . ?
N3 C4 1.385(5) . ?
N3 C5 1.374(5) . ?
O3 C1 1.264(5) . ?
O1 C5 1.231(4) . ?
N4 H4 0.8600 . ?
N4 C2 1.373(5) . ?
N4 C4 1.369(5) . ?
O2 C4 1.217(4) . ?
N1 H1 0.8600 . ?
N1 C8 1.318(5) . ?
N1 C10 1.335(5) . ?
O4 C1 1.215(5) . ?
C1 C2 1.530(5) . ?
C3 H3A 0.9300 . ?
C3 C2 1.334(5) . ?
C3 C5 1.426(5) . ?
C6 C11 1.479(5) . ?
C6 C9 1.385(6) . ?
C6 C7 1.386(6) . ?
C11 C11 1.306(8) 2_757 ?
C11 H11 0.9300 . ?
C8 H8 0.9300 . ?
C8 C7 1.366(5) . ?
C9 H9 0.9300 . ?
C9 C10 1.386(6) . ?
C10 H10 0.9300 . ?
C7 H7 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 N3 H3 116.6 . . ?
C5 N3 H3 116.6 . . ?
C5 N3 C4 126.9(3) . . ?
C2 N4 H4 118.6 . . ?
C4 N4 H4 118.6 . . ?
C4 N4 C2 122.8(3) . . ?
C8 N1 H1 119.8 . . ?
C8 N1 C10 120.5(3) . . ?
C10 N1 H1 119.8 . . ?
O3 C1 C2 113.3(3) . . ?
O4 C1 O3 127.9(4) . . ?
O4 C1 C2 118.8(4) . . ?
C2 C3 H3A 119.2 . . ?
C2 C3 C5 121.6(4) . . ?
C5 C3 H3A 119.2 . . ?
N4 C2 C1 115.5(3) . . ?
C3 C2 N4 120.4(3) . . ?
C3 C2 C1 124.0(4) . . ?
C9 C6 C11 124.7(4) . . ?
C9 C6 C7 117.7(3) . . ?
C7 C6 C11 117.6(4) . . ?
N4 C4 N3 114.3(3) . . ?
O2 C4 N3 121.5(3) . . ?
O2 C4 N4 124.2(3) . . ?
C6 C11 H11 117.4 . . ?
C11 C11 C6 125.3(5) 2_757 . ?
C11 C11 H11 117.4 2_757 . ?
N1 C8 H8 119.1 . . ?
N1 C8 C7 121.8(4) . . ?
C7 C8 H8 119.1 . . ?
C6 C9 H9 120.2 . . ?
C6 C9 C10 119.7(4) . . ?
C10 C9 H9 120.2 . . ?
N1 C10 C9 120.5(4) . . ?
N1 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
N3 C5 C3 114.0(3) . . ?
O1 C5 N3 120.6(3) . . ?
O1 C5 C3 125.4(4) . . ?
C6 C7 H7 120.1 . . ?
C8 C7 C6 119.7(4) . . ?
C8 C7 H7 120.1 . . ?

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
O3 C1 C2 N4 4.1(5) . . . . ?
O3 C1 C2 C3 -176.5(4) . . . . ?
N1 C8 C7 C6 -0.3(6) . . . . ?
O4 C1 C2 N4 -176.3(4) . . . . ?
O4 C1 C2 C3 3.1(6) . . . . ?
C2 N4 C4 N3 1.3(5) . . . . ?
C2 N4 C4 O2 -179.2(4) . . . . ?
C2 C3 C5 N3 1.7(6) . . . . ?
C2 C3 C5 O1 -179.0(4) . . . . ?
C6 C9 C10 N1 0.9(6) . . . . ?
C4 N3 C5 O1 178.8(4) . . . . ?
C4 N3 C5 C3 -1.9(6) . . . . ?
C4 N4 C2 C1 178.0(3) . . . . ?
C4 N4 C2 C3 -1.4(6) . . . . ?
C11 C6 C9 C10 176.9(4) . . . . ?
C11 C6 C7 C8 -177.3(4) . . . . ?
C8 N1 C10 C9 -0.5(6) . . . . ?
C9 C6 C11 C11 -7.2(8) . . . 2_757 ?
C9 C6 C7 C8 0.8(6) . . . . ?
C10 N1 C8 C7 0.2(6) . . . . ?
C5 N3 C4 N4 0.5(6) . . . . ?
C5 N3 C4 O2 -179.1(4) . . . . ?
C5 C3 C2 N4 -0.1(6) . . . . ?
C5 C3 C2 C1 -179.5(4) . . . . ?
C7 C6 C11 C11 170.8(6) . . . 2_757 ?
C7 C6 C9 C10 -1.0(6) . . . . ?

_shelx_SHELXL_version_number     2017/1
_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_jdm77am
_database_code_depnum_ccdc_archive 'CCDC 1574189'
_audit_update_record             
;
2018-03-25 deposited with the CCDC.
2018-05-08 downloaded from the CCDC.
;
_audit_creation_date             2017-10-09
_audit_creation_method           
;
Olex2 1.2-ac3
(compiled 2016.03.30 svn.r3266 for Rigaku Oxford Diffraction, GUI svn.r5168)     
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C12 H12 N2, 2(C5 H4 N2 O4)'
_chemical_formula_sum            'C22 H20 N6 O8'
_chemical_formula_weight         496.44
_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           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                   7.646(2)
_cell_length_b                   12.279(4)
_cell_length_c                   11.421(4)
_cell_angle_alpha                90
_cell_angle_beta                 90.411(6)
_cell_angle_gamma                90
_cell_volume                     1072.2(6)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    1165
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      20.88
_cell_measurement_theta_min      2.66
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.120
_exptl_absorpt_correction_T_max  .99
_exptl_absorpt_correction_T_min  0.895669
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS v.2.03 (Bruker,200?) was used for absorption correction.
R(int) was 0.0460 before and 0.0386 after correction.
The Ratio of minimum to maximum transmission is 0.8957.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.538
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             516
_exptl_crystal_size_max          .31
_exptl_crystal_size_mid          .24
_exptl_crystal_size_min          .16
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0640
_diffrn_reflns_av_unetI/netI     0.0484
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10093
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.991
_diffrn_reflns_theta_max         24.991
_diffrn_reflns_theta_min         2.435
_diffrn_ambient_temperature      298
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1651
_reflns_number_total             1880
_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 v6.28A (Bruker, 2002)'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'SAINT v6.28A (Bruker, 2002)'
_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    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.256
_refine_diff_density_min         -0.330
_refine_diff_density_rms         0.063
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.342
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         1880
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1136
_refine_ls_R_factor_gt           0.0983
_refine_ls_restrained_S_all      1.342
_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)+(0.0544P)²+1.3658P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1818
_refine_ls_wR_factor_ref         0.1882
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C1(H1A,H1B)
2.b Aromatic/amide H refined with riding coordinates:
 N3(H3), N2(H2), C11(H11), C6(H6), C4(H4), C5(H5), C3(H3B)
2.c Idealised tetrahedral OH refined as rotating group:
 O3(H3A)
;
_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 0.5724(4) 0.4860(2) 0.1460(2) 0.0332(8) Uani 1 1 d . . . . .
N3 N 0.4470(5) 0.6347(3) 0.0660(3) 0.0284(9) Uani 1 1 d . . . . .
H3 H 0.427377 0.596364 0.004266 0.034 Uiso 1 1 calc R . . . .
O1 O 0.2994(4) 0.7747(2) -0.0172(3) 0.0421(9) Uani 1 1 d . . . . .
O4 O 0.6791(5) 0.5122(2) 0.3821(2) 0.0417(9) Uani 1 1 d . . . . .
O3 O 0.7338(5) 0.6843(2) 0.4283(3) 0.0411(9) Uani 1 1 d . . . . .
H3A H 0.769556 0.657029 0.489476 0.062 Uiso 1 1 calc GR . . . .
N2 N 0.4331(5) 0.8006(3) 0.1604(3) 0.0302(9) Uani 1 1 d . . . . .
H2 H 0.402120 0.867896 0.163726 0.036 Uiso 1 1 calc R . . . .
C11 C 0.5253(6) 0.7576(3) 0.2504(3) 0.0276(10) Uani 1 1 d . . . . .
H11 H 0.555284 0.802935 0.312639 0.033 Uiso 1 1 calc R . . . .
C8 C 0.5764(5) 0.6523(3) 0.2551(3) 0.0237(9) Uani 1 1 d . . . . .
C9 C 0.5357(5) 0.5824(3) 0.1568(3) 0.0232(9) Uani 1 1 d . . . . .
C10 C 0.3870(6) 0.7401(3) 0.0632(3) 0.0272(10) Uani 1 1 d . . . . .
N1 N 0.8669(5) 0.5993(3) 0.6143(3) 0.0344(9) Uani 1 1 d . . . . .
C7 C 0.6688(6) 0.6091(3) 0.3618(3) 0.0264(10) Uani 1 1 d . . . . .
C6 C 1.0003(7) 0.6199(4) 0.8023(4) 0.0416(13) Uani 1 1 d . . . . .
H6 H 1.058244 0.664943 0.855318 0.050 Uiso 1 1 calc R . . . .
C2 C 0.9649(6) 0.5125(4) 0.8308(3) 0.0307(10) Uani 1 1 d . . . . .
C4 C 0.8352(6) 0.4953(4) 0.6402(4) 0.0373(11) Uani 1 1 d . . . . .
H4 H 0.779991 0.451618 0.584581 0.045 Uiso 1 1 calc R . . . .
C1 C 1.0135(7) 0.4633(4) 0.9480(3) 0.0377(11) Uani 1 1 d . . . . .
H1A H 0.944845 0.397715 0.959078 0.045 Uiso 1 1 calc R . . . .
H1B H 1.135595 0.441994 0.946049 0.045 Uiso 1 1 calc R . . . .
C5 C 0.9487(7) 0.6593(4) 0.6944(4) 0.0418(12) Uani 1 1 d . . . . .
H5 H 0.972462 0.731780 0.676839 0.050 Uiso 1 1 calc R . . . .
C3 C 0.8813(6) 0.4506(3) 0.7462(4) 0.0347(11) Uani 1 1 d . . . . .
H3B H 0.856070 0.377866 0.761324 0.042 Uiso 1 1 calc R . . . .


_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 C9 1.223(4) . ?
N3 H3 0.8600 . ?
N3 C9 1.391(5) . ?
N3 C10 1.374(5) . ?
O1 C10 1.209(5) . ?
O4 C7 1.214(5) . ?
O3 H3A 0.8200 . ?
O3 C7 1.293(5) . ?
N2 H2 0.8600 . ?
N2 C11 1.350(5) . ?
N2 C10 1.380(5) . ?
C11 H11 0.9300 . ?
C11 C8 1.351(5) . ?
C8 C9 1.446(5) . ?
C8 C7 1.501(5) . ?
N1 C4 1.333(6) . ?
N1 C5 1.328(5) . ?
C6 H6 0.9300 . ?
C6 C2 1.386(6) . ?
C6 C5 1.378(6) . ?
C2 C1 1.513(6) . ?
C2 C3 1.382(6) . ?
C4 H4 0.9300 . ?
C4 C3 1.374(6) . ?
C1 C1 1.506(8) 3_767 ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C5 H5 0.9300 . ?
C3 H3B 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C9 N3 H3 116.1 . . ?
C10 N3 H3 116.1 . . ?
C10 N3 C9 127.8(3) . . ?
C7 O3 H3A 109.5 . . ?
C11 N2 H2 119.0 . . ?
C11 N2 C10 122.1(3) . . ?
C10 N2 H2 119.0 . . ?
N2 C11 H11 118.2 . . ?
N2 C11 C8 123.6(4) . . ?
C8 C11 H11 118.2 . . ?
C11 C8 C9 118.4(4) . . ?
C11 C8 C7 120.3(4) . . ?
C9 C8 C7 121.2(3) . . ?
O2 C9 N3 118.8(3) . . ?
O2 C9 C8 127.2(4) . . ?
N3 C9 C8 114.0(3) . . ?
N3 C10 N2 113.9(3) . . ?
O1 C10 N3 122.1(4) . . ?
O1 C10 N2 123.9(4) . . ?
C5 N1 C4 117.7(4) . . ?
O4 C7 O3 124.3(4) . . ?
O4 C7 C8 122.1(3) . . ?
O3 C7 C8 113.6(3) . . ?
C2 C6 H6 120.4 . . ?
C5 C6 H6 120.4 . . ?
C5 C6 C2 119.3(4) . . ?
C6 C2 C1 122.8(4) . . ?
C3 C2 C6 116.7(4) . . ?
C3 C2 C1 120.5(4) . . ?
N1 C4 H4 118.9 . . ?
N1 C4 C3 122.1(4) . . ?
C3 C4 H4 118.9 . . ?
C2 C1 H1A 108.5 . . ?
C2 C1 H1B 108.5 . . ?
C1 C1 C2 115.1(5) 3_767 . ?
C1 C1 H1A 108.5 3_767 . ?
C1 C1 H1B 108.5 3_767 . ?
H1A C1 H1B 107.5 . . ?
N1 C5 C6 123.4(4) . . ?
N1 C5 H5 118.3 . . ?
C6 C5 H5 118.3 . . ?
C2 C3 H3B 119.7 . . ?
C4 C3 C2 120.7(4) . . ?
C4 C3 H3B 119.7 . . ?

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 C11 C8 C9 2.2(6) . . . . ?
N2 C11 C8 C7 -176.1(4) . . . . ?
C11 N2 C10 N3 -1.6(6) . . . . ?
C11 N2 C10 O1 177.3(4) . . . . ?
C11 C8 C9 O2 179.6(4) . . . . ?
C11 C8 C9 N3 0.5(6) . . . . ?
C11 C8 C7 O4 161.8(4) . . . . ?
C11 C8 C7 O3 -17.9(6) . . . . ?
C9 N3 C10 O1 -174.2(4) . . . . ?
C9 N3 C10 N2 4.7(6) . . . . ?
C9 C8 C7 O4 -16.5(6) . . . . ?
C9 C8 C7 O3 163.8(4) . . . . ?
C10 N3 C9 O2 176.6(4) . . . . ?
C10 N3 C9 C8 -4.2(6) . . . . ?
C10 N2 C11 C8 -1.7(7) . . . . ?
N1 C4 C3 C2 -0.6(7) . . . . ?
C7 C8 C9 O2 -2.0(7) . . . . ?
C7 C8 C9 N3 178.8(4) . . . . ?
C6 C2 C1 C1 39.7(8) . . . 3_767 ?
C6 C2 C3 C4 -0.7(7) . . . . ?
C2 C6 C5 N1 -0.6(8) . . . . ?
C4 N1 C5 C6 -0.6(7) . . . . ?
C1 C2 C3 C4 179.2(4) . . . . ?
C5 N1 C4 C3 1.2(7) . . . . ?
C5 C6 C2 C1 -178.7(5) . . . . ?
C5 C6 C2 C3 1.2(7) . . . . ?
C3 C2 C1 C1 -140.2(6) . . . 3_767 ?

_shelx_SHELXL_version_number     2017/1
_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_jdm53xm
_database_code_depnum_ccdc_archive 'CCDC 1574191'
_audit_update_record             
;
2018-03-25 deposited with the CCDC.
2018-05-08 downloaded from the CCDC.
;
_audit_creation_date             2017-12-05
_audit_creation_method           
;
Olex2 1.2-ac3
(compiled 2016.03.30 svn.r3266 for Rigaku Oxford Diffraction, GUI svn.r5168)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C13 H14 N2, C5 H4 N2 O4'
_chemical_formula_sum            'C18 H18 N4 O4'
_chemical_formula_weight         354.36
_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      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                   6.573(3)
_cell_length_b                   7.531(4)
_cell_length_c                   17.511(8)
_cell_angle_alpha                87.416(9)
_cell_angle_beta                 88.657(9)
_cell_angle_gamma                75.143(9)
_cell_volume                     836.9(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    650
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      20.82
_cell_measurement_theta_min      2.33
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_T_max  .89
_exptl_absorpt_correction_T_min  0.674067
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS v.2.03 (Bruker,200?) was used for absorption correction.
R(int) was 0.0471 before and 0.0360 after correction.
The Ratio of minimum to maximum transmission is 0.6741.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.406
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             374
_exptl_crystal_size_max          .36
_exptl_crystal_size_mid          .27
_exptl_crystal_size_min          .18
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0635
_diffrn_reflns_av_unetI/netI     0.1215
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            6071
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         2.329
_diffrn_ambient_temperature      298(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1359
_reflns_number_total             2913
_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 v6.28A (Bruker, 2002)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v6.28A (Bruker, 2002)'
_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    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.210
_refine_diff_density_min         -0.219
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.917
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     235
_refine_ls_number_reflns         2913
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1547
_refine_ls_R_factor_gt           0.0644
_refine_ls_restrained_S_all      0.917
_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)+(0.0533P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1229
_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 C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Riding coordinates:
 C11(H11A,H11B), O1(H1), N3(H3), N4(H4)
2.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 C17(H17), C18(H18), C15(H15), C16(H16), C9(H9), C10(H10), C6(H6), C7(H7),
 C3(H3A)
;
_atom_sites_solution_hydrogens   mixed
_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
N2 N 0.7454(5) 0.1339(4) -0.11555(18) 0.0505(9) Uani 1 1 d . . . . .
N1 N 0.1284(5) 0.6433(4) 0.39204(18) 0.0487(9) Uani 1 1 d . . . . .
C17 C 0.5866(6) 0.1608(5) -0.0669(2) 0.0529(11) Uani 1 1 d . . . . .
H17 H 0.463216 0.134106 -0.081835 0.064 Uiso 1 1 calc R . . . .
C18 C 0.5918(6) 0.2267(5) 0.0054(2) 0.0520(11) Uani 1 1 d . . . . .
H18 H 0.474211 0.242907 0.037441 0.062 Uiso 1 1 calc R . . . .
C14 C 0.7710(6) 0.2682(5) 0.0298(2) 0.0413(10) Uani 1 1 d . . . . .
C15 C 0.9383(6) 0.2417(5) -0.0217(2) 0.0515(11) Uani 1 1 d . . . . .
H15 H 1.063029 0.268485 -0.008427 0.062 Uiso 1 1 calc R . . . .
C16 C 0.9195(6) 0.1757(6) -0.0924(2) 0.0558(11) Uani 1 1 d . . . . .
H16 H 1.034024 0.159194 -0.125955 0.067 Uiso 1 1 calc R . . . .
C13 C 0.7935(6) 0.3345(6) 0.1087(2) 0.0568(12) Uani 1 1 d . . . . .
H13A H 0.897247 0.239667 0.136157 0.068 Uiso 1 1 calc R . . . .
H13B H 0.848852 0.442127 0.103022 0.068 Uiso 1 1 calc R . . . .
C12 C 0.5959(5) 0.3831(5) 0.1573(2) 0.0460(10) Uani 1 1 d . . . . .
H12A H 0.544563 0.274395 0.167321 0.055 Uiso 1 1 calc R . . . .
H12B H 0.487868 0.474108 0.129869 0.055 Uiso 1 1 calc R . . . .
C11 C 0.6390(6) 0.4587(5) 0.2323(2) 0.0483(10) Uani 1 1 d . . . . .
H11A H 0.770787 0.370252 0.257878 0.058 Uiso 1 1 d R . . . .
H11B H 0.711927 0.568862 0.219518 0.058 Uiso 1 1 d R . . . .
C8 C 0.4573(6) 0.5158(5) 0.2875(2) 0.0392(9) Uani 1 1 d . . . . .
C9 C 0.2495(6) 0.5442(5) 0.2678(2) 0.0490(10) Uani 1 1 d . . . . .
H9 H 0.215232 0.520492 0.218706 0.059 Uiso 1 1 calc R . . . .
C10 C 0.0917(6) 0.6080(5) 0.3209(2) 0.0532(11) Uani 1 1 d . . . . .
H10 H -0.047346 0.627062 0.306009 0.064 Uiso 1 1 calc R . . . .
C6 C 0.3283(6) 0.6119(5) 0.4114(2) 0.0519(11) Uani 1 1 d . . . . .
H6 H 0.357544 0.633053 0.461427 0.062 Uiso 1 1 calc R . . . .
C7 C 0.4962(6) 0.5497(5) 0.3622(2) 0.0489(11) Uani 1 1 d . . . . .
H7 H 0.633619 0.530865 0.379015 0.059 Uiso 1 1 calc R . . . .
O1 O 0.1741(4) 0.2310(4) 0.50618(14) 0.0545(8) Uani 1 1 d . . . . .
H1 H 0.082474 0.267296 0.537458 0.082 Uiso 1 1 d R . . . .
O2 O -0.0965(4) 0.1945(4) 0.43931(14) 0.0627(9) Uani 1 1 d . . . . .
O3 O -0.0002(4) 0.0710(4) 0.29328(14) 0.0631(9) Uani 1 1 d . . . . .
O4 O 0.6811(4) -0.0883(4) 0.22159(15) 0.0577(8) Uani 1 1 d . . . . .
N3 N 0.3405(4) -0.0040(4) 0.26133(16) 0.0407(8) Uani 1 1 d . . . . .
H3 H 0.302437 -0.035113 0.218355 0.049 Uiso 1 1 d R . . . .
N4 N 0.6017(4) 0.0375(4) 0.33824(16) 0.0427(8) Uani 1 1 d . . . . .
H4 H 0.730455 0.035326 0.346608 0.051 Uiso 1 1 d R . . . .
C1 C 0.0901(6) 0.1824(5) 0.4449(2) 0.0430(10) Uani 1 1 d . . . . .
C2 C 0.2467(5) 0.1136(5) 0.3848(2) 0.0359(9) Uani 1 1 d . . . . .
C3 C 0.4556(5) 0.1013(5) 0.3932(2) 0.0374(9) Uani 1 1 d . . . . .
H3A H 0.499952 0.138348 0.438532 0.045 Uiso 1 1 calc R . . . .
C4 C 0.5515(5) -0.0237(5) 0.2703(2) 0.0388(9) Uani 1 1 d . . . . .
C5 C 0.1806(5) 0.0610(5) 0.3133(2) 0.0393(9) Uani 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
N2 C17 1.312(4) . ?
N2 C16 1.339(5) . ?
N1 C10 1.325(4) . ?
N1 C6 1.324(4) . ?
C17 H17 0.9300 . ?
C17 C18 1.385(5) . ?
C18 H18 0.9300 . ?
C18 C14 1.375(5) . ?
C14 C15 1.385(5) . ?
C14 C13 1.513(5) . ?
C15 H15 0.9300 . ?
C15 C16 1.375(5) . ?
C16 H16 0.9300 . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C12 1.509(4) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 C11 1.516(4) . ?
C11 H11A 1.0438 . ?
C11 H11B 1.0726 . ?
C11 C8 1.505(5) . ?
C8 C9 1.377(5) . ?
C8 C7 1.387(5) . ?
C9 H9 0.9300 . ?
C9 C10 1.383(5) . ?
C10 H10 0.9300 . ?
C6 H6 0.9300 . ?
C6 C7 1.381(5) . ?
C7 H7 0.9300 . ?
O1 H1 0.8068 . ?
O1 C1 1.325(4) . ?
O2 C1 1.212(4) . ?
O3 C5 1.229(4) . ?
O4 C4 1.217(4) . ?
N3 H3 0.8594 . ?
N3 C4 1.369(4) . ?
N3 C5 1.380(4) . ?
N4 H4 0.8583 . ?
N4 C3 1.357(4) . ?
N4 C4 1.372(4) . ?
C1 C2 1.470(5) . ?
C2 C3 1.364(4) . ?
C2 C5 1.440(5) . ?
C3 H3A 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C17 N2 C16 116.4(3) . . ?
C6 N1 C10 116.5(3) . . ?
N2 C17 H17 118.1 . . ?
N2 C17 C18 123.9(4) . . ?
C18 C17 H17 118.1 . . ?
C17 C18 H18 120.0 . . ?
C14 C18 C17 120.0(3) . . ?
C14 C18 H18 120.0 . . ?
C18 C14 C15 116.3(3) . . ?
C18 C14 C13 123.6(3) . . ?
C15 C14 C13 120.0(3) . . ?
C14 C15 H15 120.1 . . ?
C16 C15 C14 119.9(4) . . ?
C16 C15 H15 120.1 . . ?
N2 C16 C15 123.5(4) . . ?
N2 C16 H16 118.2 . . ?
C15 C16 H16 118.2 . . ?
C14 C13 H13A 108.2 . . ?
C14 C13 H13B 108.2 . . ?
H13A C13 H13B 107.3 . . ?
C12 C13 C14 116.4(3) . . ?
C12 C13 H13A 108.2 . . ?
C12 C13 H13B 108.2 . . ?
C13 C12 H12A 109.5 . . ?
C13 C12 H12B 109.5 . . ?
C13 C12 C11 110.6(3) . . ?
H12A C12 H12B 108.1 . . ?
C11 C12 H12A 109.5 . . ?
C11 C12 H12B 109.5 . . ?
C12 C11 H11A 109.7 . . ?
C12 C11 H11B 107.9 . . ?
H11A C11 H11B 95.7 . . ?
C8 C11 C12 117.5(3) . . ?
C8 C11 H11A 112.6 . . ?
C8 C11 H11B 111.2 . . ?
C9 C8 C11 123.9(3) . . ?
C9 C8 C7 116.7(3) . . ?
C7 C8 C11 119.4(3) . . ?
C8 C9 H9 120.0 . . ?
C8 C9 C10 120.1(4) . . ?
C10 C9 H9 120.0 . . ?
N1 C10 C9 123.4(4) . . ?
N1 C10 H10 118.3 . . ?
C9 C10 H10 118.3 . . ?
N1 C6 H6 117.9 . . ?
N1 C6 C7 124.2(4) . . ?
C7 C6 H6 117.9 . . ?
C8 C7 H7 120.4 . . ?
C6 C7 C8 119.1(4) . . ?
C6 C7 H7 120.4 . . ?
C1 O1 H1 109.2 . . ?
C4 N3 H3 116.6 . . ?
C4 N3 C5 127.5(3) . . ?
C5 N3 H3 115.9 . . ?
C3 N4 H4 118.3 . . ?
C3 N4 C4 122.6(3) . . ?
C4 N4 H4 119.0 . . ?
O1 C1 C2 112.9(3) . . ?
O2 C1 O1 123.2(3) . . ?
O2 C1 C2 123.9(3) . . ?
C3 C2 C1 122.3(3) . . ?
C3 C2 C5 117.7(3) . . ?
C5 C2 C1 120.0(3) . . ?
N4 C3 C2 122.8(3) . . ?
N4 C3 H3A 118.6 . . ?
C2 C3 H3A 118.6 . . ?
O4 C4 N3 122.4(3) . . ?
O4 C4 N4 123.7(3) . . ?
N3 C4 N4 114.0(3) . . ?
O3 C5 N3 117.2(3) . . ?
O3 C5 C2 127.5(3) . . ?
N3 C5 C2 115.2(3) . . ?

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 C17 C18 C14 0.1(6) . . . . ?
N1 C6 C7 C8 -0.4(6) . . . . ?
C17 N2 C16 C15 0.7(6) . . . . ?
C17 C18 C14 C15 0.6(6) . . . . ?
C17 C18 C14 C13 -177.8(4) . . . . ?
C18 C14 C15 C16 -0.6(6) . . . . ?
C18 C14 C13 C12 -9.3(6) . . . . ?
C14 C15 C16 N2 -0.1(6) . . . . ?
C14 C13 C12 C11 -176.3(3) . . . . ?
C15 C14 C13 C12 172.3(3) . . . . ?
C16 N2 C17 C18 -0.7(6) . . . . ?
C13 C14 C15 C16 177.9(4) . . . . ?
C13 C12 C11 C8 179.5(3) . . . . ?
C12 C11 C8 C9 -15.7(5) . . . . ?
C12 C11 C8 C7 166.9(3) . . . . ?
C11 C8 C9 C10 -175.9(4) . . . . ?
C11 C8 C7 C6 176.5(4) . . . . ?
C8 C9 C10 N1 -0.6(6) . . . . ?
C9 C8 C7 C6 -1.1(5) . . . . ?
C10 N1 C6 C7 1.5(6) . . . . ?
C6 N1 C10 C9 -1.0(6) . . . . ?
C7 C8 C9 C10 1.6(5) . . . . ?
O1 C1 C2 C3 0.5(5) . . . . ?
O1 C1 C2 C5 -177.8(3) . . . . ?
O2 C1 C2 C3 -179.8(4) . . . . ?
O2 C1 C2 C5 1.9(6) . . . . ?
C1 C2 C3 N4 179.8(3) . . . . ?
C1 C2 C5 O3 2.4(6) . . . . ?
C1 C2 C5 N3 -179.1(3) . . . . ?
C3 N4 C4 O4 -176.9(3) . . . . ?
C3 N4 C4 N3 3.8(5) . . . . ?
C3 C2 C5 O3 -176.0(4) . . . . ?
C3 C2 C5 N3 2.5(5) . . . . ?
C4 N3 C5 O3 178.7(3) . . . . ?
C4 N3 C5 C2 0.0(5) . . . . ?
C4 N4 C3 C2 -1.4(5) . . . . ?
C5 N3 C4 O4 177.6(3) . . . . ?
C5 N3 C4 N4 -3.1(5) . . . . ?
C5 C2 C3 N4 -1.9(5) . . . . ?

_shelx_SHELXL_version_number     2017/1
_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_flmvn_0ma_a
_database_code_depnum_ccdc_archive 'CCDC 1574196'
_audit_update_record             
;
2018-04-22 deposited with the CCDC.
2018-05-08 downloaded from the CCDC.
;
_audit_creation_date             2018-01-19
_audit_creation_method           
;
Olex2 1.2-ac3
(compiled 2016.03.30 svn.r3266 for Rigaku Oxford Diffraction, GUI svn.r5168)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H10 N2, 2(C5 H4 N2 O4)'
_chemical_formula_sum            'C22 H18 N6 O8'
_chemical_formula_weight         494.42
_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                   12.528(9)
_cell_length_b                   6.992(5)
_cell_length_c                   13.266(8)
_cell_angle_alpha                90
_cell_angle_beta                 113.80(2)
_cell_angle_gamma                90
_cell_volume                     1063.3(12)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    8521
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      29.43
_cell_measurement_theta_min      2.91
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.121
_exptl_absorpt_correction_T_max  .974
_exptl_absorpt_correction_T_min  .947
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS v.2.03 (Bruker,200?) was used for absorption correction.
R(int) was 0.0470 before and 0.0329 after correction.
The Ratio of minimum to maximum transmission is 0.8537.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.544
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       rod
_exptl_crystal_F_000             512
_exptl_crystal_size_max          .35
_exptl_crystal_size_mid          .31
_exptl_crystal_size_min          .28
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1146
_diffrn_reflns_av_unetI/netI     0.0450
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            12072
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         3.100
_diffrn_ambient_temperature      100.01
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_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                1678
_reflns_number_total             1866
_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       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_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 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.310
_refine_diff_density_min         -0.351
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       0.023(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     168
_refine_ls_number_reflns         1866
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0457
_refine_ls_R_factor_gt           0.0409
_refine_ls_restrained_S_all      1.042
_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)+(0.0613P)²+0.6636P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1146
_refine_ls_wR_factor_ref         0.1197
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N2(H2A), N1(H1), C3(H3), C9(H9), C10(H10), C11(H11), C7(H7), C6(H6)
;
_atom_sites_solution_hydrogens   mixed
_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
O3 O 0.81700(9) 0.90639(17) 0.66957(9) 0.0165(3) Uani 1 1 d . . . . .
O4 O 0.91773(9) 0.94609(17) 0.36422(9) 0.0179(3) Uani 1 1 d . . . . .
O1 O 0.59843(10) 0.76818(19) 0.61400(10) 0.0211(3) Uani 1 1 d . . . . .
O2 O 0.49408(10) 0.75963(19) 0.42381(10) 0.0214(3) Uani 1 1 d . . . . .
N2 N 0.74706(11) 0.8346(2) 0.32980(11) 0.0145(3) Uani 1 1 d . . . . .
H2A H 0.734392 0.812560 0.260593 0.017 Uiso 1 1 calc R . . . .
N1 N 0.86338(11) 0.92647(19) 0.51520(11) 0.0132(3) Uani 1 1 d . . . . .
H1 H 0.931429 0.973018 0.559590 0.016 Uiso 1 1 calc R . . . .
N3 N 0.33128(11) 0.6826(2) 0.48051(12) 0.0168(4) Uani 1 1 d . . . . .
C4 C 0.84853(13) 0.9052(2) 0.40163(13) 0.0135(4) Uani 1 1 d . . . . .
C3 C 0.66727(13) 0.8000(2) 0.36826(14) 0.0146(4) Uani 1 1 d . . . . .
H3 H 0.593791 0.754861 0.317218 0.018 Uiso 1 1 calc R . . . .
C5 C 0.78869(13) 0.8859(2) 0.56519(13) 0.0127(4) Uani 1 1 d . . . . .
C9 C 0.24397(14) 0.6258(2) 0.61014(14) 0.0149(4) Uani 1 1 d . . . . .
H9 H 0.247229 0.620679 0.682884 0.018 Uiso 1 1 calc R . . . .
C8 C 0.14404(13) 0.5808(2) 0.51718(14) 0.0142(4) Uani 1 1 d . . . . .
C1 C 0.58869(13) 0.7821(2) 0.51404(13) 0.0145(4) Uani 1 1 d . . . . .
C2 C 0.68101(13) 0.8241(2) 0.48017(13) 0.0134(4) Uani 1 1 d . . . . .
C10 C 0.33387(13) 0.6764(2) 0.58787(14) 0.0176(4) Uani 1 1 d . . . . .
H10 H 0.404434 0.710664 0.647700 0.021 Uiso 1 1 calc R . . . .
C11 C 0.04913(13) 0.5242(2) 0.54074(14) 0.0144(4) Uani 1 1 d . . . . .
H11 H 0.055852 0.520947 0.614657 0.017 Uiso 1 1 calc R . . . .
C7 C 0.14204(13) 0.5883(2) 0.40514(14) 0.0162(4) Uani 1 1 d . . . . .
H7 H 0.072659 0.556974 0.343194 0.019 Uiso 1 1 calc R . . . .
C6 C 0.23643(14) 0.6386(2) 0.39121(14) 0.0163(4) Uani 1 1 d . . . . .
H6 H 0.236896 0.643280 0.319822 0.020 Uiso 1 1 calc R . . . .
H2 H 0.437(3) 0.737(4) 0.455(2) 0.066(8) 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
O3 C5 1.291(2) . ?
O4 C4 1.195(2) . ?
O1 C1 1.285(2) . ?
O2 C1 1.310(2) . ?
O2 H2 0.98(3) . ?
N2 H2A 0.8800 . ?
N2 C4 1.338(2) . ?
N2 C3 1.315(2) . ?
N1 H1 0.8800 . ?
N1 C4 1.449(2) . ?
N1 C5 1.377(2) . ?
N3 C10 1.412(2) . ?
N3 C6 1.332(2) . ?
C3 H3 0.9500 . ?
C3 C2 1.434(2) . ?
C5 C2 1.432(2) . ?
C9 H9 0.9500 . ?
C9 C8 1.393(2) . ?
C9 C10 1.323(2) . ?
C8 C11 1.403(2) . ?
C8 C7 1.477(3) . ?
C1 C2 1.430(2) . ?
C10 H10 0.9500 . ?
C11 C11 1.313(3) 3_566 ?
C11 H11 0.9500 . ?
C7 H7 0.9500 . ?
C7 C6 1.316(2) . ?
C6 H6 0.9500 . ?

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
C1 O2 H2 100.3(17) . . ?
C4 N2 H2A 121.8 . . ?
C3 N2 H2A 121.8 . . ?
C3 N2 C4 116.36(15) . . ?
C4 N1 H1 114.6 . . ?
C5 N1 H1 114.6 . . ?
C5 N1 C4 130.72(13) . . ?
C6 N3 C10 122.63(14) . . ?
O4 C4 N2 115.64(16) . . ?
O4 C4 N1 126.67(15) . . ?
N2 C4 N1 117.69(14) . . ?
N2 C3 H3 117.0 . . ?
N2 C3 C2 125.98(15) . . ?
C2 C3 H3 117.0 . . ?
O3 C5 N1 123.21(14) . . ?
O3 C5 C2 129.93(14) . . ?
N1 C5 C2 106.86(15) . . ?
C8 C9 H9 123.1 . . ?
C10 C9 H9 123.1 . . ?
C10 C9 C8 113.87(16) . . ?
C9 C8 C11 113.96(16) . . ?
C9 C8 C7 121.79(15) . . ?
C11 C8 C7 124.22(15) . . ?
O1 C1 O2 127.42(15) . . ?
O1 C1 C2 125.98(15) . . ?
O2 C1 C2 106.60(15) . . ?
C5 C2 C3 122.16(14) . . ?
C1 C2 C3 121.78(14) . . ?
C1 C2 C5 116.03(15) . . ?
N3 C10 H10 118.0 . . ?
C9 C10 N3 123.94(15) . . ?
C9 C10 H10 118.0 . . ?
C8 C11 H11 120.4 . . ?
C11 C11 C8 119.1(2) 3_566 . ?
C11 C11 H11 120.4 3_566 . ?
C8 C7 H7 120.0 . . ?
C6 C7 C8 119.96(15) . . ?
C6 C7 H7 120.0 . . ?
N3 C6 H6 121.1 . . ?
C7 C6 N3 117.80(16) . . ?
C7 C6 H6 121.1 . . ?

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
O3 C5 C2 C3 -176.54(15) . . . . ?
O3 C5 C2 C1 1.6(3) . . . . ?
O1 C1 C2 C3 167.50(15) . . . . ?
O1 C1 C2 C5 -10.7(2) . . . . ?
O2 C1 C2 C3 -12.0(2) . . . . ?
O2 C1 C2 C5 169.82(14) . . . . ?
N2 C3 C2 C5 -1.8(3) . . . . ?
N2 C3 C2 C1 -179.90(15) . . . . ?
N1 C5 C2 C3 4.4(2) . . . . ?
N1 C5 C2 C1 -177.44(13) . . . . ?
C4 N2 C3 C2 -2.5(2) . . . . ?
C4 N1 C5 O3 177.22(14) . . . . ?
C4 N1 C5 C2 -3.6(2) . . . . ?
C3 N2 C4 O4 -175.94(14) . . . . ?
C3 N2 C4 N1 3.4(2) . . . . ?
C5 N1 C4 O4 179.08(16) . . . . ?
C5 N1 C4 N2 -0.2(3) . . . . ?
C9 C8 C11 C11 -179.04(19) . . . 3_566 ?
C9 C8 C7 C6 0.0(2) . . . . ?
C8 C9 C10 N3 -0.9(2) . . . . ?
C8 C7 C6 N3 -0.5(2) . . . . ?
C10 N3 C6 C7 0.3(2) . . . . ?
C10 C9 C8 C11 179.05(15) . . . . ?
C10 C9 C8 C7 0.6(2) . . . . ?
C11 C8 C7 C6 -178.23(16) . . . . ?
C7 C8 C11 C11 -0.6(3) . . . 3_566 ?
C6 N3 C10 C9 0.5(3) . . . . ?

_shelx_SHELXL_version_number     2017/1
_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_jmv62m
_database_code_depnum_ccdc_archive 'CCDC 1574193'
_audit_update_record             
;
2018-03-25 deposited with the CCDC.
2018-05-08 downloaded from the CCDC.
;
_audit_creation_date             2017-10-09
_audit_creation_method           
;
Olex2 1.2-ac3
(compiled 2016.03.30 svn.r3266 for Rigaku Oxford Diffraction, GUI svn.r5168)      
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C12 H13 N2, C5 H3 N2 O4'
_chemical_formula_sum            'C17 H16 N4 O4'
_chemical_formula_weight         340.34
_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           43
_space_group_name_H-M_alt        'F d d 2'
_space_group_name_Hall           'F 2 -2d'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z'
'x+1/4, -y+1/4, z+1/4'
'-x+1/4, y+1/4, z+1/4'
'x, y+1/2, z+1/2'
'-x, -y+1/2, z+1/2'
'x+1/4, -y+3/4, z+3/4'
'-x+1/4, y+3/4, z+3/4'
'x+1/2, y, z+1/2'
'-x+1/2, -y, z+1/2'
'x+3/4, -y+1/4, z+3/4'
'-x+3/4, y+1/4, z+3/4'
'x+1/2, y+1/2, z'
'-x+1/2, -y+1/2, z'
'x+3/4, -y+3/4, z+1/4'
'-x+3/4, y+3/4, z+1/4'

_cell_length_a                   29.689(7)
_cell_length_b                   44.694(11)
_cell_length_c                   4.8880(12)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     6486(3)
_cell_formula_units_Z            16
_cell_measurement_reflns_used    3306
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      23.54
_cell_measurement_theta_min      2.28
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_T_max  .93
_exptl_absorpt_correction_T_min  0.866664
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS v.2.03 (Bruker,200?) was used for absorption correction.
R(int) was 0.0428 before and 0.0292 after correction.
The Ratio of minimum to maximum transmission is 0.8667.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.394
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             2848
_exptl_crystal_size_max          .37
_exptl_crystal_size_mid          .26
_exptl_crystal_size_min          .18
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0393
_diffrn_reflns_av_unetI/netI     0.0308
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       34
_diffrn_reflns_limit_h_min       -34
_diffrn_reflns_limit_k_max       52
_diffrn_reflns_limit_k_min       -52
_diffrn_reflns_limit_l_max       5
_diffrn_reflns_limit_l_min       -5
_diffrn_reflns_number            15489
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         2.281
_diffrn_ambient_temperature      298
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.774
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     1.000
_reflns_number_gt                2666
_reflns_number_total             2847
_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 v6.28A (Bruker, 2002)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v6.28A (Bruker, 2002)'
_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    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.158
_refine_diff_density_min         -0.274
_refine_diff_density_rms         0.044
_refine_ls_abs_structure_details 
;
 Flack x determined using 940 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.6(8)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.200
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     234
_refine_ls_number_reflns         2847
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0603
_refine_ls_R_factor_gt           0.0557
_refine_ls_restrained_S_all      1.199
_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)+(0.0481P)²+5.9721P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1169
_refine_ls_wR_factor_ref         0.1190
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C17(H17A,H17B)
2.b Aromatic/amide H refined with riding coordinates:
 N5(H5A), C5(H5), C6(H6), C10(H10), C11(H11), C12(H12), C13(H13), C15(H15),
 C16(H16), N3(H3)
;
_atom_sites_solution_hydrogens   mixed
_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
C1 C 0.34978(12) 0.06717(8) 0.9728(8) 0.0367(9) Uani 1 1 d . . . . .
N5 N 0.36765(11) 0.09375(7) 0.8879(8) 0.0492(9) Uani 1 1 d . . . . .
H5A H 0.358276 0.109919 0.964439 0.059 Uiso 1 1 calc R . . . .
C3 C 0.13000(12) 0.05673(9) 0.2055(8) 0.0398(9) Uani 1 1 d . . . . .
H3A H 0.137200 0.072349 0.336162 0.048 Uiso 1 1 calc R . . . .
H3B H 0.127493 0.038018 0.304767 0.048 Uiso 1 1 calc R . . . .
C4 C 0.31328(12) 0.06925(8) 1.1874(8) 0.0372(9) Uani 1 1 d . . . . .
C5 C 0.03616(14) 0.09266(9) 0.3979(10) 0.0506(11) Uani 1 1 d . . . . .
H5 H 0.050311 0.110284 0.344679 0.061 Uiso 1 1 calc R . . . .
C6 C 0.17960(12) 0.02678(8) -0.1106(8) 0.0377(9) Uani 1 1 d . . . . .
H6 H 0.165080 0.009393 -0.054565 0.045 Uiso 1 1 calc R . . . .
C7 C 0.04782(12) 0.06571(9) 0.2780(8) 0.0398(10) Uani 1 1 d . . . . .
C8 C 0.39755(12) 0.04105(8) 0.6564(9) 0.0377(9) Uani 1 1 d . . . . .
C9 C 0.16733(11) 0.05432(8) 0.0001(8) 0.0333(8) Uani 1 1 d . . . . .
C10 C 0.18984(13) 0.07934(9) -0.0955(9) 0.0448(10) Uani 1 1 d . . . . .
H10 H 0.182598 0.098109 -0.026165 0.054 Uiso 1 1 calc R . . . .
C11 C 0.21301(12) 0.02549(8) -0.3014(8) 0.0378(9) Uani 1 1 d . . . . .
H11 H 0.221489 0.007032 -0.372580 0.045 Uiso 1 1 calc R . . . .
C12 C 0.02530(13) 0.04061(9) 0.3645(10) 0.0448(10) Uani 1 1 d . . . . .
H12 H 0.032109 0.022027 0.289641 0.054 Uiso 1 1 calc R . . . .
C13 C 0.22261(13) 0.07680(8) -0.2908(9) 0.0447(11) Uani 1 1 d . . . . .
H13 H 0.237102 0.093829 -0.355582 0.054 Uiso 1 1 calc R . . . .
C14 C 0.39990(13) 0.09606(8) 0.6864(9) 0.0432(10) Uani 1 1 d . . . . .
C15 C 0.00350(14) 0.09309(9) 0.5962(10) 0.0536(12) Uani 1 1 d . . . . .
H15 H -0.003550 0.111310 0.677453 0.064 Uiso 1 1 calc R . . . .
C16 C -0.00748(13) 0.04310(9) 0.5631(9) 0.0472(11) Uani 1 1 d . . . . .
H16 H -0.022441 0.025846 0.618334 0.057 Uiso 1 1 calc R . . . .
C17 C 0.08499(13) 0.06383(10) 0.0699(9) 0.0495(11) Uani 1 1 d . . . . .
H17A H 0.087251 0.082722 -0.026831 0.059 Uiso 1 1 calc R . . . .
H17B H 0.077897 0.048379 -0.062598 0.059 Uiso 1 1 calc R . . . .
H1 H 0.4302(11) 0.0698(7) 0.470(7) 0.012(9) Uiso 1 1 d . . . . .
H18 H 0.3549(14) 0.0259(9) 0.919(10) 0.054(13) Uiso 1 1 d . . . . .
N1 N 0.41282(11) 0.06908(7) 0.5820(8) 0.0396(8) Uani 1 1 d . . . . .
C18 C 0.36411(12) 0.04189(9) 0.8645(9) 0.0374(9) Uani 1 1 d . . . . .
N3 N 0.23374(10) 0.05019(7) -0.3877(7) 0.0377(8) Uani 1 1 d . . . . .
H3 H 0.254706 0.048794 -0.508422 0.045 Uiso 1 1 calc R . . . .
N4 N -0.01872(10) 0.06875(7) 0.6788(7) 0.0441(9) Uani 1 1 d . . . . .
O1 O 0.41222(10) 0.01839(6) 0.5459(8) 0.0596(9) Uani 1 1 d . . . . .
O2 O 0.41561(11) 0.11972(6) 0.6090(8) 0.0729(11) Uani 1 1 d . . . . .
O3 O 0.29578(9) 0.04446(6) 1.2505(6) 0.0516(8) Uani 1 1 d . . . . .
O4 O 0.30351(11) 0.09361(6) 1.2785(8) 0.0639(10) Uani 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
C1 N5 1.366(5) . ?
C1 C4 1.511(5) . ?
C1 C18 1.318(5) . ?
N5 H5A 0.8600 . ?
N5 C14 1.377(5) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C9 1.499(5) . ?
C3 C17 1.525(5) . ?
C4 O3 1.262(4) . ?
C4 O4 1.212(4) . ?
C5 H5 0.9300 . ?
C5 C7 1.384(6) . ?
C5 C15 1.371(6) . ?
C6 H6 0.9300 . ?
C6 C9 1.393(5) . ?
C6 C11 1.363(5) . ?
C7 C12 1.373(5) . ?
C7 C17 1.503(5) . ?
C8 N1 1.381(5) . ?
C8 C18 1.422(5) . ?
C8 O1 1.228(4) . ?
C9 C10 1.384(5) . ?
C10 H10 0.9300 . ?
C10 C13 1.368(6) . ?
C11 H11 0.9300 . ?
C11 N3 1.333(5) . ?
C12 H12 0.9300 . ?
C12 C16 1.379(6) . ?
C13 H13 0.9300 . ?
C13 N3 1.322(5) . ?
C14 N1 1.364(5) . ?
C14 O2 1.216(4) . ?
C15 H15 0.9300 . ?
C15 N4 1.335(5) . ?
C16 H16 0.9300 . ?
C16 N4 1.321(5) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
N1 H1 0.75(3) . ?
C18 H18 0.81(4) . ?
N3 H3 0.8600 . ?

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
N5 C1 C4 115.8(3) . . ?
C18 C1 N5 119.9(3) . . ?
C18 C1 C4 124.3(3) . . ?
C1 N5 H5A 118.2 . . ?
C1 N5 C14 123.5(3) . . ?
C14 N5 H5A 118.2 . . ?
H3A C3 H3B 107.9 . . ?
C9 C3 H3A 109.3 . . ?
C9 C3 H3B 109.3 . . ?
C9 C3 C17 111.8(3) . . ?
C17 C3 H3A 109.3 . . ?
C17 C3 H3B 109.3 . . ?
O3 C4 C1 114.2(3) . . ?
O4 C4 C1 118.8(3) . . ?
O4 C4 O3 126.9(4) . . ?
C7 C5 H5 120.4 . . ?
C15 C5 H5 120.4 . . ?
C15 C5 C7 119.2(4) . . ?
C9 C6 H6 120.2 . . ?
C11 C6 H6 120.2 . . ?
C11 C6 C9 119.6(3) . . ?
C5 C7 C17 121.3(4) . . ?
C12 C7 C5 117.3(4) . . ?
C12 C7 C17 121.4(4) . . ?
N1 C8 C18 113.2(3) . . ?
O1 C8 N1 121.1(4) . . ?
O1 C8 C18 125.7(3) . . ?
C6 C9 C3 121.1(3) . . ?
C10 C9 C3 121.7(3) . . ?
C10 C9 C6 117.2(3) . . ?
C9 C10 H10 119.6 . . ?
C13 C10 C9 120.8(4) . . ?
C13 C10 H10 119.6 . . ?
C6 C11 H11 119.4 . . ?
N3 C11 C6 121.2(3) . . ?
N3 C11 H11 119.4 . . ?
C7 C12 H12 120.2 . . ?
C7 C12 C16 119.7(4) . . ?
C16 C12 H12 120.2 . . ?
C10 C13 H13 119.9 . . ?
N3 C13 C10 120.2(3) . . ?
N3 C13 H13 119.9 . . ?
N1 C14 N5 113.4(3) . . ?
O2 C14 N5 123.6(4) . . ?
O2 C14 N1 123.0(4) . . ?
C5 C15 H15 118.2 . . ?
N4 C15 C5 123.5(4) . . ?
N4 C15 H15 118.2 . . ?
C12 C16 H16 118.3 . . ?
N4 C16 C12 123.3(4) . . ?
N4 C16 H16 118.3 . . ?
C3 C17 H17A 109.4 . . ?
C3 C17 H17B 109.4 . . ?
C7 C17 C3 111.2(3) . . ?
C7 C17 H17A 109.4 . . ?
C7 C17 H17B 109.4 . . ?
H17A C17 H17B 108.0 . . ?
C8 N1 H1 117(2) . . ?
C14 N1 C8 127.7(4) . . ?
C14 N1 H1 115(2) . . ?
C1 C18 C8 122.4(4) . . ?
C1 C18 H18 121(3) . . ?
C8 C18 H18 117(3) . . ?
C11 N3 H3 119.5 . . ?
C13 N3 C11 121.1(3) . . ?
C13 N3 H3 119.5 . . ?
C16 N4 C15 116.9(3) . . ?

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
C1 N5 C14 N1 -0.9(6) . . . . ?
C1 N5 C14 O2 179.4(4) . . . . ?
N5 C1 C4 O3 176.3(4) . . . . ?
N5 C1 C4 O4 -3.1(5) . . . . ?
N5 C1 C18 C8 -1.0(6) . . . . ?
N5 C14 N1 C8 -0.3(6) . . . . ?
C3 C9 C10 C13 -177.4(4) . . . . ?
C4 C1 N5 C14 -177.4(4) . . . . ?
C4 C1 C18 C8 177.9(4) . . . . ?
C5 C7 C12 C16 0.1(6) . . . . ?
C5 C7 C17 C3 92.1(5) . . . . ?
C5 C15 N4 C16 1.1(7) . . . . ?
C6 C9 C10 C13 0.1(6) . . . . ?
C6 C11 N3 C13 0.1(6) . . . . ?
C7 C5 C15 N4 -1.2(7) . . . . ?
C7 C12 C16 N4 -0.3(7) . . . . ?
C9 C3 C17 C7 179.1(3) . . . . ?
C9 C6 C11 N3 -1.1(6) . . . . ?
C9 C10 C13 N3 -1.1(7) . . . . ?
C10 C13 N3 C11 1.0(6) . . . . ?
C11 C6 C9 C3 178.5(3) . . . . ?
C11 C6 C9 C10 1.0(6) . . . . ?
C12 C7 C17 C3 -85.3(5) . . . . ?
C12 C16 N4 C15 -0.3(7) . . . . ?
C15 C5 C7 C12 0.6(6) . . . . ?
C15 C5 C7 C17 -176.9(4) . . . . ?
C17 C3 C9 C6 -93.8(4) . . . . ?
C17 C3 C9 C10 83.7(5) . . . . ?
C17 C7 C12 C16 177.6(4) . . . . ?
N1 C8 C18 C1 -0.2(6) . . . . ?
C18 C1 N5 C14 1.6(6) . . . . ?
C18 C1 C4 O3 -2.6(6) . . . . ?
C18 C1 C4 O4 178.0(4) . . . . ?
C18 C8 N1 C14 0.8(6) . . . . ?
O1 C8 N1 C14 -179.7(4) . . . . ?
O1 C8 C18 C1 -179.6(4) . . . . ?
O2 C14 N1 C8 179.4(4) . . . . ?

_shelx_SHELXL_version_number     2017/1
_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_jdm49m
_database_code_depnum_ccdc_archive 'CCDC 1574192'
_audit_update_record             
;
2018-03-25 deposited with the CCDC.
2018-05-08 downloaded from the CCDC.
;
_audit_creation_date             2017-12-05
_audit_creation_method           
;
Olex2 1.2-ac3
(compiled 2016.03.30 svn.r3266 for Rigaku Oxford Diffraction, GUI svn.r5168)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C5 H3 N2 O4, C5 H7 N2, 3(H2 O)'
_chemical_formula_sum            'C10 H16 N4 O7'
_chemical_formula_weight         304.27
_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                   6.988(4)
_cell_length_b                   17.855(10)
_cell_length_c                   11.428(6)
_cell_angle_alpha                90
_cell_angle_beta                 103.035(11)
_cell_angle_gamma                90
_cell_volume                     1389.3(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    841
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      20.10
_cell_measurement_theta_min      2.28
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.124
_exptl_absorpt_correction_T_max  .96
_exptl_absorpt_correction_T_min  0.813005
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS v.2.03 (Bruker,200?) was used for absorption correction.
R(int) was 0.1099 before and 0.0469 after correction.
The Ratio of minimum to maximum transmission is 0.8130.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.455
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             616
_exptl_crystal_size_max          .43
_exptl_crystal_size_mid          .35
_exptl_crystal_size_min          .27
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0927
_diffrn_reflns_av_unetI/netI     0.0796
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            13179
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         2.156
_diffrn_ambient_temperature      298
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1340
_reflns_number_total             2448
_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 v6.28A (Bruker, 2002)'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'SAINT v6.28A (Bruker, 2002)'
_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    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.180
_refine_diff_density_min         -0.227
_refine_diff_density_rms         0.049
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.955
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     199
_refine_ls_number_reflns         2448
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1174
_refine_ls_R_factor_gt           0.0537
_refine_ls_restrained_S_all      0.955
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0611P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1168
_refine_ls_wR_factor_ref         0.1409
_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 O(H,H) groups
2.a Free rotating group:
 O5(H5A,H5B), O7(H7A,H7B), O6(H6A,H6B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3), N1(H1), N3(H3A), C7(H7), N2(H2), C9(H9), C6(H6), C10(H10)
2.c X=CH2 refined with riding coordinates:
 N4(H4A,H4B)
;
_atom_sites_solution_hydrogens   mixed
_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
C4 C 0.1384(4) 0.59325(14) 0.7817(2) 0.0330(7) Uani 1 1 d . . . . .
O3 O 0.2034(3) 0.48839(11) 0.91038(16) 0.0552(6) Uani 1 1 d . . . . .
O2 O 0.0828(3) 0.48321(10) 0.65863(16) 0.0539(7) Uani 1 1 d . . . . .
C3 C 0.1290(4) 0.66889(15) 0.7745(2) 0.0378(7) Uani 1 1 d . . . . .
H3 H 0.156116 0.696180 0.845672 0.045 Uiso 1 1 calc R . . . .
N1 N 0.0477(3) 0.59560(12) 0.56763(19) 0.0415(6) Uani 1 1 d . . . . .
H1 H 0.021554 0.571748 0.500527 0.050 Uiso 1 1 calc R . . . .
N3 N 0.6987(4) 0.57581(14) 0.8713(2) 0.0488(7) Uani 1 1 d . . . . .
H3A H 0.727825 0.545718 0.931471 0.059 Uiso 1 1 calc R . . . .
O4 O 0.2296(4) 0.60073(11) 0.99162(17) 0.0605(7) Uani 1 1 d . . . . .
C7 C 0.5861(4) 0.59395(16) 0.6635(2) 0.0437(8) Uani 1 1 d . . . . .
H7 H 0.543496 0.573701 0.587036 0.052 Uiso 1 1 calc R . . . .
N2 N 0.0825(3) 0.70676(12) 0.67016(19) 0.0409(6) Uani 1 1 d . . . . .
H2 H 0.078345 0.754856 0.672602 0.049 Uiso 1 1 calc R . . . .
C1 C 0.0913(4) 0.55199(15) 0.6705(2) 0.0355(7) Uani 1 1 d . . . . .
C9 C 0.6670(4) 0.69866(16) 0.7970(2) 0.0416(8) Uani 1 1 d . . . . .
H9 H 0.680338 0.749875 0.811256 0.050 Uiso 1 1 calc R . . . .
C2 C 0.0413(4) 0.67228(15) 0.5600(3) 0.0396(7) Uani 1 1 d . . . . .
N4 N 0.5479(4) 0.71887(13) 0.5874(2) 0.0544(8) Uani 1 1 d . . . . .
H4A H 0.558183 0.766410 0.599173 0.065 Uiso 1 1 calc R . . . .
H4B H 0.505474 0.701687 0.515899 0.065 Uiso 1 1 calc R . . . .
C5 C 0.1937(4) 0.55830(16) 0.9031(2) 0.0380(7) Uani 1 1 d . . . . .
O1 O 0.0049(3) 0.70544(11) 0.46525(17) 0.0588(7) Uani 1 1 d . . . . .
C8 C 0.5973(4) 0.67209(15) 0.6792(2) 0.0362(7) Uani 1 1 d . . . . .
C6 C 0.6376(5) 0.54865(16) 0.7596(3) 0.0484(9) Uani 1 1 d . . . . .
H6 H 0.630523 0.497053 0.748308 0.058 Uiso 1 1 calc R . . . .
O5 O 0.4111(4) 0.63596(17) 0.37241(19) 0.0820(9) Uani 1 1 d . . . . .
H5A H 0.293273 0.631769 0.332448 0.123 Uiso 1 1 d G . . . .
H5B H 0.489073 0.630978 0.325619 0.123 Uiso 1 1 d G . . . .
C10 C 0.7144(5) 0.65018(17) 0.8888(3) 0.0466(8) Uani 1 1 d . . . . .
H10 H 0.759052 0.668523 0.966337 0.056 Uiso 1 1 calc R . . . .
O7 O 0.4381(4) 0.37899(11) 0.8352(2) 0.0606(7) Uani 1 1 d . . . . .
H7A H 0.348621 0.411244 0.834779 0.091 Uiso 1 1 d G . . . .
H7B H 0.541393 0.391578 0.886318 0.091 Uiso 1 1 d G . . . .
O6 O 0.0642(4) 0.63442(11) 0.1831(2) 0.0616(7) Uani 1 1 d . . . . .
H6A H -0.021087 0.604514 0.199080 0.092 Uiso 1 1 d G . . . .
H6B H 0.101403 0.618912 0.121538 0.092 Uiso 1 1 d G . . . .


_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
C4 C3 1.354(4) . ?
C4 C1 1.441(3) . ?
C4 C5 1.491(3) . ?
O3 C5 1.252(3) . ?
O2 C1 1.236(3) . ?
C3 H3 0.9300 . ?
C3 N2 1.346(3) . ?
N1 H1 0.8600 . ?
N1 C1 1.386(3) . ?
N1 C2 1.372(3) . ?
N3 H3A 0.8600 . ?
N3 C6 1.342(3) . ?
N3 C10 1.344(4) . ?
O4 C5 1.243(3) . ?
C7 H7 0.9300 . ?
C7 C8 1.407(4) . ?
C7 C6 1.347(4) . ?
N2 H2 0.8600 . ?
N2 C2 1.372(3) . ?
C9 H9 0.9300 . ?
C9 C8 1.406(4) . ?
C9 C10 1.343(4) . ?
C2 O1 1.210(3) . ?
N4 H4A 0.8600 . ?
N4 H4B 0.8600 . ?
N4 C8 1.325(3) . ?
C6 H6 0.9300 . ?
O5 H5A 0.8500 . ?
O5 H5B 0.8498 . ?
C10 H10 0.9300 . ?
O7 H7A 0.8496 . ?
O7 H7B 0.8502 . ?
O6 H6A 0.8501 . ?
O6 H6B 0.8499 . ?

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
C3 C4 C1 117.3(2) . . ?
C3 C4 C5 118.2(2) . . ?
C1 C4 C5 124.5(2) . . ?
C4 C3 H3 118.2 . . ?
N2 C3 C4 123.6(2) . . ?
N2 C3 H3 118.2 . . ?
C1 N1 H1 116.1 . . ?
C2 N1 H1 116.1 . . ?
C2 N1 C1 127.8(2) . . ?
C6 N3 H3A 120.1 . . ?
C6 N3 C10 119.8(2) . . ?
C10 N3 H3A 120.1 . . ?
C8 C7 H7 120.2 . . ?
C6 C7 H7 120.2 . . ?
C6 C7 C8 119.6(3) . . ?
C3 N2 H2 118.4 . . ?
C3 N2 C2 123.1(2) . . ?
C2 N2 H2 118.4 . . ?
O2 C1 C4 126.9(2) . . ?
O2 C1 N1 118.0(2) . . ?
N1 C1 C4 115.1(2) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 H9 119.9 . . ?
C10 C9 C8 120.1(3) . . ?
N1 C2 N2 113.1(2) . . ?
O1 C2 N1 122.9(3) . . ?
O1 C2 N2 124.0(3) . . ?
H4A N4 H4B 120.0 . . ?
C8 N4 H4A 120.0 . . ?
C8 N4 H4B 120.0 . . ?
O3 C5 C4 118.6(2) . . ?
O4 C5 C4 117.7(2) . . ?
O4 C5 O3 123.7(2) . . ?
C9 C8 C7 117.0(2) . . ?
N4 C8 C7 121.8(3) . . ?
N4 C8 C9 121.2(3) . . ?
N3 C6 C7 121.9(3) . . ?
N3 C6 H6 119.1 . . ?
C7 C6 H6 119.1 . . ?
H5A O5 H5B 109.5 . . ?
N3 C10 H10 119.2 . . ?
C9 C10 N3 121.5(3) . . ?
C9 C10 H10 119.2 . . ?
H7A O7 H7B 109.5 . . ?
H6A O6 H6B 109.4 . . ?

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
C4 C3 N2 C2 -0.5(4) . . . . ?
C3 C4 C1 O2 -176.5(3) . . . . ?
C3 C4 C1 N1 2.2(4) . . . . ?
C3 C4 C5 O3 -179.8(3) . . . . ?
C3 C4 C5 O4 -0.5(4) . . . . ?
C3 N2 C2 N1 1.5(4) . . . . ?
C3 N2 C2 O1 -177.7(3) . . . . ?
C1 C4 C3 N2 -1.4(4) . . . . ?
C1 C4 C5 O3 1.1(4) . . . . ?
C1 C4 C5 O4 -179.6(3) . . . . ?
C1 N1 C2 N2 -0.6(4) . . . . ?
C1 N1 C2 O1 178.7(3) . . . . ?
C2 N1 C1 C4 -1.2(4) . . . . ?
C2 N1 C1 O2 177.6(3) . . . . ?
C5 C4 C3 N2 179.4(3) . . . . ?
C5 C4 C1 O2 2.6(5) . . . . ?
C5 C4 C1 N1 -178.7(3) . . . . ?
C8 C7 C6 N3 0.4(5) . . . . ?
C8 C9 C10 N3 0.6(5) . . . . ?
C6 N3 C10 C9 1.1(5) . . . . ?
C6 C7 C8 C9 1.3(4) . . . . ?
C6 C7 C8 N4 -179.9(3) . . . . ?
C10 N3 C6 C7 -1.6(5) . . . . ?
C10 C9 C8 C7 -1.8(4) . . . . ?
C10 C9 C8 N4 179.3(3) . . . . ?

_shelx_SHELXL_version_number     2017/1
_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_fic4am
_database_code_depnum_ccdc_archive 'CCDC 1574195'
_audit_update_record             
;
2018-03-25 deposited with the CCDC.
2018-05-08 downloaded from the CCDC.
;
_audit_creation_date             2017-11-03
_audit_creation_method           
;
Olex2 1.2-ac3
(compiled 2016.03.30 svn.r3266 for Rigaku Oxford Diffraction, GUI svn.r5168)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C5 H3 N2 O4, C5 H7 N2'
_chemical_formula_sum            'C10 H10 N4 O4'
_chemical_formula_weight         250.22
_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           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   7.0875(8)
_cell_length_b                   11.9657(13)
_cell_length_c                   24.919(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2113.3(4)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4205
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      23.68
_cell_measurement_theta_min      2.99
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.125
_exptl_absorpt_correction_T_max  0.986
_exptl_absorpt_correction_T_min  0.909364
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS v.2.03 (Bruker,200?) was used for absorption correction.
R(int) was 0.0337 before and 0.0297 after correction.
The Ratio of minimum to maximum transmission is 0.9094.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.573
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             1040
_exptl_crystal_size_max          .56
_exptl_crystal_size_mid          .22
_exptl_crystal_size_min          .16
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0384
_diffrn_reflns_av_unetI/netI     0.0187
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            18669
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.998
_diffrn_reflns_theta_max         24.998
_diffrn_reflns_theta_min         3.270
_diffrn_ambient_temperature      298
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1836
_reflns_number_total             1859
_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 v6.28A (Bruker, 2002)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v6.28A (Bruker, 2002)'
_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    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.229
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.358
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         1859
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0819
_refine_ls_R_factor_gt           0.0809
_refine_ls_restrained_S_all      1.358
_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)+(0.0289P)²+3.6799P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1523
_refine_ls_wR_factor_ref         0.1528
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H,H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C8(H8), C5(H5), C2(H2A), C4(H4), C3(H3)
2.b X=CH2 refined with riding coordinates:
 N4(H4A,H4B)
;
_atom_sites_solution_hydrogens   mixed
_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
C8 C 1.0227(5) 0.1775(3) 0.17074(13) 0.0312(8) Uani 1 1 d . . . . .
H8 H 1.034137 0.161447 0.134372 0.037 Uiso 1 1 calc R . . . .
C7 C 0.9558(5) 0.2772(3) 0.18585(12) 0.0280(8) Uani 1 1 d . . . . .
C9 C 1.0769(5) 0.0953(3) 0.20928(13) 0.0288(8) Uani 1 1 d . . . . .
C10 C 0.9928(5) 0.2300(3) 0.27921(12) 0.0299(8) Uani 1 1 d . . . . .
C1 C 0.2260(5) 0.9054(3) -0.01760(13) 0.0322(8) Uani 1 1 d . . . . .
C6 C 0.8923(5) 0.3665(3) 0.14574(13) 0.0326(8) Uani 1 1 d . . . . .
C5 C 0.1380(6) 0.8190(3) 0.01135(14) 0.0414(9) Uani 1 1 d . . . . .
H5 H 0.101544 0.754058 -0.006333 0.050 Uiso 1 1 calc R . . . .
C2 C 0.2746(5) 1.0016(3) 0.01134(16) 0.0426(9) Uani 1 1 d . . . . .
H2A H 0.328395 1.062371 -0.006148 0.051 Uiso 1 1 calc R . . . .
C4 C 0.1061(6) 0.8293(3) 0.06442(15) 0.0481(10) Uani 1 1 d . . . . .
H4 H 0.045444 0.772033 0.082844 0.058 Uiso 1 1 calc R . . . .
C3 C 0.2431(6) 1.0055(4) 0.06476(17) 0.0515(11) Uani 1 1 d . . . . .
H3 H 0.279497 1.068701 0.083873 0.062 Uiso 1 1 calc R . . . .
H2 H 0.902(5) 0.369(3) 0.2498(14) 0.034(10) Uiso 1 1 d . . . . .
H1 H 1.088(6) 0.077(3) 0.2878(16) 0.051(12) Uiso 1 1 d . . . . .
H3A H 0.137(6) 0.932(4) 0.1247(19) 0.065(14) Uiso 1 1 d . . . . .
N2 N 0.9431(4) 0.3029(2) 0.23931(10) 0.0301(7) Uani 1 1 d . . . . .
N1 N 1.0560(4) 0.1278(2) 0.26173(11) 0.0312(7) Uani 1 1 d . . . . .
N3 N 0.1608(5) 0.9209(3) 0.09086(13) 0.0515(10) Uani 1 1 d . . . . .
N4 N 0.2631(5) 0.8941(3) -0.06934(11) 0.0477(9) Uani 1 1 d . . . . .
H4A H 0.319138 0.946951 -0.086459 0.057 Uiso 1 1 calc R . . . .
H4B H 0.231194 0.833894 -0.085857 0.057 Uiso 1 1 calc R . . . .
O3 O 0.9818(4) 0.2526(2) 0.32647(9) 0.0469(7) Uani 1 1 d . . . . .
O4 O 1.1391(4) 0.00102(19) 0.19873(9) 0.0385(6) Uani 1 1 d . . . . .
O2 O 0.8651(4) 0.4619(2) 0.16322(10) 0.0504(8) Uani 1 1 d . . . . .
O1 O 0.8749(4) 0.3342(2) 0.09867(9) 0.0481(7) Uani 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
C8 H8 0.9300 . ?
C8 C7 1.338(4) . ?
C8 C9 1.428(5) . ?
C7 C6 1.531(4) . ?
C7 N2 1.370(4) . ?
C9 N1 1.372(4) . ?
C9 O4 1.239(4) . ?
C10 N2 1.368(4) . ?
C10 N1 1.373(4) . ?
C10 O3 1.211(4) . ?
C1 C5 1.407(5) . ?
C1 C2 1.401(5) . ?
C1 N4 1.323(4) . ?
C6 O2 1.237(4) . ?
C6 O1 1.241(4) . ?
C5 H5 0.9300 . ?
C5 C4 1.347(5) . ?
C2 H2A 0.9300 . ?
C2 C3 1.351(6) . ?
C4 H4 0.9300 . ?
C4 N3 1.336(5) . ?
C3 H3 0.9300 . ?
C3 N3 1.337(6) . ?
N2 H2 0.88(4) . ?
N1 H1 0.92(4) . ?
N3 H3A 0.87(5) . ?
N4 H4A 0.8600 . ?
N4 H4B 0.8600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C7 C8 H8 119.3 . . ?
C7 C8 C9 121.4(3) . . ?
C9 C8 H8 119.3 . . ?
C8 C7 C6 122.9(3) . . ?
C8 C7 N2 119.8(3) . . ?
N2 C7 C6 117.3(3) . . ?
N1 C9 C8 114.6(3) . . ?
O4 C9 C8 125.5(3) . . ?
O4 C9 N1 119.9(3) . . ?
N2 C10 N1 114.9(3) . . ?
O3 C10 N2 123.2(3) . . ?
O3 C10 N1 121.9(3) . . ?
C2 C1 C5 116.7(3) . . ?
N4 C1 C5 120.8(3) . . ?
N4 C1 C2 122.5(3) . . ?
O2 C6 C7 117.4(3) . . ?
O2 C6 O1 127.2(3) . . ?
O1 C6 C7 115.4(3) . . ?
C1 C5 H5 119.6 . . ?
C4 C5 C1 120.7(4) . . ?
C4 C5 H5 119.6 . . ?
C1 C2 H2A 120.1 . . ?
C3 C2 C1 119.7(4) . . ?
C3 C2 H2A 120.1 . . ?
C5 C4 H4 119.7 . . ?
N3 C4 C5 120.7(4) . . ?
N3 C4 H4 119.7 . . ?
C2 C3 H3 119.2 . . ?
N3 C3 C2 121.7(4) . . ?
N3 C3 H3 119.2 . . ?
C7 N2 H2 121(2) . . ?
C10 N2 C7 123.2(3) . . ?
C10 N2 H2 116(2) . . ?
C9 N1 C10 126.2(3) . . ?
C9 N1 H1 117(2) . . ?
C10 N1 H1 116(2) . . ?
C4 N3 C3 120.5(3) . . ?
C4 N3 H3A 123(3) . . ?
C3 N3 H3A 116(3) . . ?
C1 N4 H4A 120.0 . . ?
C1 N4 H4B 120.0 . . ?
H4A N4 H4B 120.0 . . ?

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
C8 C7 C6 O2 -167.4(4) . . . . ?
C8 C7 C6 O1 12.3(5) . . . . ?
C8 C7 N2 C10 -1.2(5) . . . . ?
C8 C9 N1 C10 -1.3(5) . . . . ?
C7 C8 C9 N1 -0.6(5) . . . . ?
C7 C8 C9 O4 179.7(3) . . . . ?
C9 C8 C7 C6 -178.6(3) . . . . ?
C9 C8 C7 N2 1.7(5) . . . . ?
C1 C5 C4 N3 -1.3(6) . . . . ?
C1 C2 C3 N3 -2.1(6) . . . . ?
C6 C7 N2 C10 179.1(3) . . . . ?
C5 C1 C2 C3 2.6(5) . . . . ?
C5 C4 N3 C3 2.0(6) . . . . ?
C2 C1 C5 C4 -1.0(6) . . . . ?
C2 C3 N3 C4 -0.3(6) . . . . ?
N2 C7 C6 O2 12.3(5) . . . . ?
N2 C7 C6 O1 -168.1(3) . . . . ?
N2 C10 N1 C9 1.7(5) . . . . ?
N1 C10 N2 C7 -0.5(5) . . . . ?
N4 C1 C5 C4 177.8(4) . . . . ?
N4 C1 C2 C3 -176.1(4) . . . . ?
O3 C10 N2 C7 179.9(3) . . . . ?
O3 C10 N1 C9 -178.7(4) . . . . ?
O4 C9 N1 C10 178.5(3) . . . . ?

_shelx_SHELXL_version_number     2017/1
_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_jm8vm
_database_code_depnum_ccdc_archive 'CCDC 1574194'
_audit_update_record             
;
2018-03-25 deposited with the CCDC.
2018-05-08 downloaded from the CCDC.
;
_audit_creation_date             2017-12-04
_audit_creation_method           
;
Olex2 1.2-ac3
(compiled 2016.03.30 svn.r3266 for Rigaku Oxford Diffraction, GUI svn.r5168)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C13 H16 N2, 2(C5 H3 N2 O4), 2(H2 O)'
_chemical_formula_sum            'C23 H26 N6 O10'
_chemical_formula_weight         546.50
_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           33
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
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'

_cell_length_a                   34.001(5)
_cell_length_b                   8.9797(14)
_cell_length_c                   8.9700(14)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2738.7(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1724
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      19.59
_cell_measurement_theta_min      2.35
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.106
_exptl_absorpt_correction_T_max  .945
_exptl_absorpt_correction_T_min  0.838266
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS v.2.03 (Bruker,200?) was used for absorption correction.
R(int) was 0.0466 before and 0.0418 after correction.
The Ratio of minimum to maximum transmission is 0.8383.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.325
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1144
_exptl_crystal_size_max          .46
_exptl_crystal_size_mid          .31
_exptl_crystal_size_min          .19
_exptl_special_details           
;
 The data collection nominally covered a full sphere of reciprocal space by
 a combination of 4 sets of ω scans each set at different φ and/or
 2θ angles and each scan (8 s exposure) covering -0.300° degrees in ω.
 The crystal to detector distance was 5.96 cm.
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0684
_diffrn_reflns_av_unetI/netI     0.0771
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       40
_diffrn_reflns_limit_h_min       -35
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_number            18985
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        24.983
_diffrn_reflns_theta_max         24.983
_diffrn_reflns_theta_min         2.565
_diffrn_ambient_temperature      298
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.995
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.871
_reflns_Friedel_fraction_full    0.997
_reflns_Friedel_fraction_max     0.997
_reflns_number_gt                3633
_reflns_number_total             4804
_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 v6.28A (Bruker, 2002)'
_computing_data_collection       'SMART v5.630 (Bruker, 2003)'
_computing_data_reduction        'SAINT v6.28A (Bruker, 2002)'
_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    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         1.471
_refine_diff_density_min         -0.320
_refine_diff_density_rms         0.108
_refine_ls_abs_structure_details 
;
 Flack x determined using 1266 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.2(10)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     358
_refine_ls_number_reflns         4804
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1143
_refine_ls_R_factor_gt           0.0902
_refine_ls_restrained_S_all      1.070
_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)+(0.1986P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2626
_refine_ls_wR_factor_ref         0.2823
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups
 At 1.5 times of:
  All O(H,H) groups
2.a Free rotating group:
 O10(H10A,H10B), O9(H9A,H9B)
2.b Secondary CH2 refined with riding coordinates:
 C17(H17A,H17B), C18(H18A,H18B), C22(H22A,H22B)
2.c Aromatic/amide H refined with riding coordinates:
 N2(H2), N1(H1), C3(H3), N3(H3A), N4(H4), C7(H7), N5(H5), C11(H11), N6(H6),
 C12(H12), C13(H13), C14(H14), C16(H16), C19(H19), C20(H20), C23(H23)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_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 -1.30580(18) -0.9622(7) -0.8111(7) 0.0424(16) Uani 1 1 d . . . . .
O7 O -1.19106(19) -1.1618(8) -1.0428(8) 0.0466(16) Uani 1 1 d . . . . .
N2 N -1.2559(2) -0.8360(8) -0.6956(8) 0.0319(17) Uani 1 1 d . . . . .
H2 H -1.273406 -0.787978 -0.645622 0.038 Uiso 1 1 calc R . . . .
O8 O -1.13898(17) -1.0416(7) -0.9534(8) 0.0414(16) Uani 1 1 d . . . . .
N1 N -1.24203(19) -1.0093(7) -0.8771(7) 0.0263(15) Uani 1 1 d . . . . .
H1 H -1.249510 -1.072877 -0.942968 0.032 Uiso 1 1 calc R . . . .
O6 O -1.20994(16) -0.7108(7) -0.5696(6) 0.0376(15) Uani 1 1 d . . . . .
C1 C -1.2021(2) -0.9836(9) -0.8597(9) 0.0291(18) Uani 1 1 d . . . . .
C2 C -1.2694(2) -0.9397(9) -0.7963(9) 0.0279(18) Uani 1 1 d . . . . .
C3 C -1.1896(2) -0.8828(9) -0.7569(9) 0.0303(19) Uani 1 1 d . . . . .
H3 H -1.162856 -0.865704 -0.743976 0.036 Uiso 1 1 calc R . . . .
C4 C -1.1754(3) -1.0684(9) -0.9625(9) 0.0297(18) Uani 1 1 d . . . . .
C5 C -1.2180(2) -0.8023(9) -0.6676(9) 0.0276(18) Uani 1 1 d . . . . .
O2 O -0.68907(19) -0.4308(8) -0.4414(8) 0.0465(17) Uani 1 1 d . . . . .
O3 O -0.71354(18) 0.0360(7) -0.8943(7) 0.0415(16) Uani 1 1 d . . . . .
O4 O -0.80767(17) -0.2242(7) -0.6518(7) 0.0405(15) Uani 1 1 d . . . . .
N3 N -0.7596(2) -0.0938(8) -0.7690(7) 0.0293(16) Uani 1 1 d . . . . .
H3A H -0.777329 -0.045065 -0.816762 0.035 Uiso 1 1 calc R . . . .
N4 N -0.74308(19) -0.2704(7) -0.5929(7) 0.0301(16) Uani 1 1 d . . . . .
H4 H -0.749639 -0.337537 -0.529198 0.036 Uiso 1 1 calc R . . . .
O1 O -0.64010(18) -0.2931(7) -0.5270(8) 0.0478(17) Uani 1 1 d . . . . .
C6 C -0.7041(2) -0.2412(8) -0.6124(9) 0.0248(17) Uani 1 1 d . . . . .
C7 C -0.6925(2) -0.1407(9) -0.7130(10) 0.0311(19) Uani 1 1 d . . . . .
H7 H -0.665807 -0.123459 -0.727170 0.037 Uiso 1 1 calc R . . . .
C8 C -0.7725(2) -0.1985(9) -0.6698(9) 0.0272(18) Uani 1 1 d . . . . .
N5 N -1.1367(2) -0.6757(10) -0.4447(10) 0.045(2) Uani 1 1 d . . . . .
H5 H -1.159770 -0.681863 -0.483231 0.054 Uiso 1 1 calc R . . . .
C9 C -0.7210(2) -0.0581(9) -0.8005(9) 0.0281(18) Uani 1 1 d . . . . .
C10 C -0.6760(2) -0.3300(9) -0.5191(9) 0.0286(18) Uani 1 1 d . . . . .
C11 C -1.1191(3) -0.5436(12) -0.4412(11) 0.044(2) Uani 1 1 d . . . . .
H11 H -1.131353 -0.460860 -0.482693 0.052 Uiso 1 1 calc R . . . .
N6 N -0.8626(2) -0.4107(10) -0.5375(10) 0.047(2) Uani 1 1 d . . . . .
H6 H -0.842966 -0.380731 -0.589811 0.056 Uiso 1 1 calc R . . . .
C12 C -0.8996(3) -0.6051(10) -0.4447(11) 0.039(2) Uani 1 1 d . . . . .
H12 H -0.904409 -0.706920 -0.439755 0.046 Uiso 1 1 calc R . . . .
C13 C -0.8833(3) -0.3107(12) -0.4647(14) 0.057(3) Uani 1 1 d . . . . .
H13 H -0.877320 -0.210113 -0.473727 0.069 Uiso 1 1 calc R . . . .
C14 C -1.0829(3) -0.5298(11) -0.3765(12) 0.049(3) Uani 1 1 d . . . . .
H14 H -1.070783 -0.437148 -0.370917 0.059 Uiso 1 1 calc R . . . .
C15 C -1.0639(2) -0.6578(10) -0.3176(10) 0.038(2) Uani 1 1 d . . . . .
C16 C -0.8704(3) -0.5527(11) -0.5347(12) 0.047(2) Uani 1 1 d . . . . .
H16 H -0.855993 -0.618191 -0.593792 0.056 Uiso 1 1 calc R . . . .
C17 C -0.9546(3) -0.5603(16) -0.2621(13) 0.062(3) Uani 1 1 d . . . . .
H17A H -0.959405 -0.485187 -0.186464 0.074 Uiso 1 1 calc R . . . .
H17B H -0.946699 -0.651097 -0.211822 0.074 Uiso 1 1 calc R . . . .
C18 C -1.0250(3) -0.6400(14) -0.2441(14) 0.056(3) Uani 1 1 d . . . . .
H18A H -1.017521 -0.734552 -0.200253 0.067 Uiso 1 1 calc R . . . .
H18B H -1.027652 -0.568469 -0.163636 0.067 Uiso 1 1 calc R . . . .
C19 C -0.9141(3) -0.3559(12) -0.3748(14) 0.057(3) Uani 1 1 d . . . . .
H19 H -0.929326 -0.286476 -0.323998 0.069 Uiso 1 1 calc R . . . .
C20 C -1.1203(3) -0.7976(11) -0.3917(12) 0.049(2) Uani 1 1 d . . . . .
H20 H -1.133324 -0.888347 -0.399195 0.058 Uiso 1 1 calc R . . . .
C21 C -0.9218(3) -0.5091(11) -0.3617(11) 0.042(2) Uani 1 1 d . . . . .
C22 C -0.9925(3) -0.5889(12) -0.3468(10) 0.043(2) Uani 1 1 d . . . . .
H22A H -1.000533 -0.498264 -0.397063 0.052 Uiso 1 1 calc R . . . .
H22B H -0.987859 -0.664414 -0.422131 0.052 Uiso 1 1 calc R . . . .
C23 C -1.0836(3) -0.7904(12) -0.3246(12) 0.050(2) Uani 1 1 d . . . . .
H23 H -1.072417 -0.875805 -0.284333 0.060 Uiso 1 1 calc R . . . .
O10 O -0.6052(2) -0.3538(11) -0.2389(10) 0.064(2) Uani 1 1 d . . . . .
H10A H -0.616224 -0.368529 -0.155084 0.096 Uiso 1 1 d G . . . .
H10B H -0.622344 -0.359566 -0.307787 0.096 Uiso 1 1 d G . . . .
O9 O -1.0912(3) -1.0349(15) -0.7064(15) 0.107(4) Uani 1 1 d . . . . .
H9A H -1.108268 -1.042142 -0.775287 0.160 Uiso 1 1 d G . . . .
H9B H -1.094516 -1.104685 -0.643731 0.160 Uiso 1 1 d G . . . .


_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 C2 1.261(10) . ?
O7 C4 1.227(10) . ?
N2 H2 0.8600 . ?
N2 C2 1.376(10) . ?
N2 C5 1.350(10) . ?
O8 C4 1.263(10) . ?
N1 H1 0.8600 . ?
N1 C1 1.385(11) . ?
N1 C2 1.335(11) . ?
O6 C5 1.234(10) . ?
C1 C3 1.361(12) . ?
C1 C4 1.503(12) . ?
C3 H3 0.9300 . ?
C3 C5 1.447(11) . ?
O2 C10 1.226(10) . ?
O3 C9 1.220(9) . ?
O4 C8 1.227(10) . ?
N3 H3A 0.8600 . ?
N3 C8 1.368(10) . ?
N3 C9 1.379(11) . ?
N4 H4 0.8600 . ?
N4 C6 1.361(10) . ?
N4 C8 1.377(11) . ?
O1 C10 1.267(10) . ?
C6 C7 1.336(11) . ?
C6 C10 1.501(11) . ?
C7 H7 0.9300 . ?
C7 C9 1.450(11) . ?
N5 H5 0.8600 . ?
N5 C11 1.329(13) . ?
N5 C20 1.317(13) . ?
C11 H11 0.9300 . ?
C11 C14 1.366(15) . ?
N6 H6 0.8600 . ?
N6 C13 1.314(15) . ?
N6 C16 1.302(13) . ?
C12 H12 0.9300 . ?
C12 C16 1.364(14) . ?
C12 C21 1.368(14) . ?
C13 H13 0.9300 . ?
C13 C19 1.381(16) . ?
C14 H14 0.9300 . ?
C14 C15 1.420(14) . ?
C15 C18 1.485(13) . ?
C15 C23 1.368(13) . ?
C16 H16 0.9300 . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C17 C21 1.502(13) . ?
C17 C22 1.516(13) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 C22 1.512(13) . ?
C19 H19 0.9300 . ?
C19 C21 1.405(14) . ?
C20 H20 0.9300 . ?
C20 C23 1.386(15) . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 H23 0.9300 . ?
O10 H10A 0.8497 . ?
O10 H10B 0.8503 . ?
O9 H9A 0.8511 . ?
O9 H9B 0.8496 . ?

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
C2 N2 H2 116.8 . . ?
C5 N2 H2 116.8 . . ?
C5 N2 C2 126.3(7) . . ?
C1 N1 H1 118.5 . . ?
C2 N1 H1 118.5 . . ?
C2 N1 C1 122.9(7) . . ?
N1 C1 C4 116.1(7) . . ?
C3 C1 N1 119.6(8) . . ?
C3 C1 C4 124.3(7) . . ?
O5 C2 N2 120.3(7) . . ?
O5 C2 N1 123.5(7) . . ?
N1 C2 N2 116.2(7) . . ?
C1 C3 H3 120.0 . . ?
C1 C3 C5 120.0(7) . . ?
C5 C3 H3 120.0 . . ?
O7 C4 O8 126.5(8) . . ?
O7 C4 C1 116.2(7) . . ?
O8 C4 C1 117.2(7) . . ?
N2 C5 C3 115.0(7) . . ?
O6 C5 N2 119.5(8) . . ?
O6 C5 C3 125.5(7) . . ?
C8 N3 H3A 116.6 . . ?
C8 N3 C9 126.8(7) . . ?
C9 N3 H3A 116.6 . . ?
C6 N4 H4 118.2 . . ?
C6 N4 C8 123.5(7) . . ?
C8 N4 H4 118.2 . . ?
N4 C6 C10 116.5(7) . . ?
C7 C6 N4 120.3(7) . . ?
C7 C6 C10 123.2(7) . . ?
C6 C7 H7 119.6 . . ?
C6 C7 C9 120.9(7) . . ?
C9 C7 H7 119.6 . . ?
O4 C8 N3 121.9(7) . . ?
O4 C8 N4 123.6(7) . . ?
N3 C8 N4 114.5(7) . . ?
C11 N5 H5 118.5 . . ?
C20 N5 H5 118.5 . . ?
C20 N5 C11 122.9(8) . . ?
O3 C9 N3 120.0(8) . . ?
O3 C9 C7 126.1(8) . . ?
N3 C9 C7 113.9(7) . . ?
O2 C10 O1 125.1(8) . . ?
O2 C10 C6 118.6(7) . . ?
O1 C10 C6 116.4(7) . . ?
N5 C11 H11 120.1 . . ?
N5 C11 C14 119.7(10) . . ?
C14 C11 H11 120.1 . . ?
C13 N6 H6 118.3 . . ?
C16 N6 H6 118.3 . . ?
C16 N6 C13 123.4(9) . . ?
C16 C12 H12 119.7 . . ?
C16 C12 C21 120.5(8) . . ?
C21 C12 H12 119.7 . . ?
N6 C13 H13 120.2 . . ?
N6 C13 C19 119.7(10) . . ?
C19 C13 H13 120.2 . . ?
C11 C14 H14 120.2 . . ?
C11 C14 C15 119.7(9) . . ?
C15 C14 H14 120.2 . . ?
C14 C15 C18 118.9(9) . . ?
C23 C15 C14 117.6(8) . . ?
C23 C15 C18 123.4(9) . . ?
N6 C16 C12 119.7(10) . . ?
N6 C16 H16 120.1 . . ?
C12 C16 H16 120.1 . . ?
H17A C17 H17B 107.8 . . ?
C21 C17 H17A 109.1 . . ?
C21 C17 H17B 109.1 . . ?
C21 C17 C22 112.6(8) . . ?
C22 C17 H17A 109.1 . . ?
C22 C17 H17B 109.1 . . ?
C15 C18 H18A 108.7 . . ?
C15 C18 H18B 108.7 . . ?
C15 C18 C22 114.4(10) . . ?
H18A C18 H18B 107.6 . . ?
C22 C18 H18A 108.7 . . ?
C22 C18 H18B 108.7 . . ?
C13 C19 H19 120.7 . . ?
C13 C19 C21 118.5(10) . . ?
C21 C19 H19 120.7 . . ?
N5 C20 H20 120.1 . . ?
N5 C20 C23 119.9(9) . . ?
C23 C20 H20 120.1 . . ?
C12 C21 C17 122.8(10) . . ?
C12 C21 C19 117.9(9) . . ?
C19 C21 C17 119.3(10) . . ?
C17 C22 H22A 109.3 . . ?
C17 C22 H22B 109.3 . . ?
C18 C22 C17 111.5(8) . . ?
C18 C22 H22A 109.3 . . ?
C18 C22 H22B 109.3 . . ?
H22A C22 H22B 108.0 . . ?
C15 C23 C20 120.2(10) . . ?
C15 C23 H23 119.9 . . ?
C20 C23 H23 119.9 . . ?
H10A O10 H10B 109.4 . . ?
H9A O9 H9B 109.4 . . ?

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
N1 C1 C3 C5 -0.6(12) . . . . ?
N1 C1 C4 O7 -6.2(11) . . . . ?
N1 C1 C4 O8 176.8(7) . . . . ?
C1 N1 C2 O5 180.0(8) . . . . ?
C1 N1 C2 N2 1.8(11) . . . . ?
C1 C3 C5 N2 0.1(11) . . . . ?
C1 C3 C5 O6 178.6(8) . . . . ?
C2 N2 C5 O6 -177.0(7) . . . . ?
C2 N2 C5 C3 1.6(12) . . . . ?
C2 N1 C1 C3 -0.4(12) . . . . ?
C2 N1 C1 C4 -178.5(7) . . . . ?
C3 C1 C4 O7 175.8(8) . . . . ?
C3 C1 C4 O8 -1.2(12) . . . . ?
C4 C1 C3 C5 177.3(7) . . . . ?
C5 N2 C2 O5 179.3(8) . . . . ?
C5 N2 C2 N1 -2.5(12) . . . . ?
N4 C6 C7 C9 1.6(12) . . . . ?
N4 C6 C10 O2 6.1(11) . . . . ?
N4 C6 C10 O1 -173.6(7) . . . . ?
C6 N4 C8 O4 -179.6(8) . . . . ?
C6 N4 C8 N3 0.1(11) . . . . ?
C6 C7 C9 O3 179.7(9) . . . . ?
C6 C7 C9 N3 0.1(12) . . . . ?
C7 C6 C10 O2 -172.2(9) . . . . ?
C7 C6 C10 O1 8.1(12) . . . . ?
C8 N3 C9 O3 178.5(8) . . . . ?
C8 N3 C9 C7 -1.9(12) . . . . ?
C8 N4 C6 C7 -1.8(12) . . . . ?
C8 N4 C6 C10 179.9(7) . . . . ?
N5 C11 C14 C15 2.0(14) . . . . ?
N5 C20 C23 C15 -2.1(15) . . . . ?
C9 N3 C8 O4 -178.4(8) . . . . ?
C9 N3 C8 N4 1.8(12) . . . . ?
C10 C6 C7 C9 179.9(7) . . . . ?
C11 N5 C20 C23 2.0(15) . . . . ?
C11 C14 C15 C18 -178.4(9) . . . . ?
C11 C14 C15 C23 -2.0(14) . . . . ?
N6 C13 C19 C21 1.2(16) . . . . ?
C13 N6 C16 C12 -4.6(15) . . . . ?
C13 C19 C21 C12 -3.1(15) . . . . ?
C13 C19 C21 C17 178.9(10) . . . . ?
C14 C15 C18 C22 -64.9(13) . . . . ?
C14 C15 C23 C20 2.1(14) . . . . ?
C15 C18 C22 C17 175.1(10) . . . . ?
C16 N6 C13 C19 2.7(16) . . . . ?
C16 C12 C21 C17 179.3(9) . . . . ?
C16 C12 C21 C19 1.3(14) . . . . ?
C18 C15 C23 C20 178.2(10) . . . . ?
C20 N5 C11 C14 -2.0(15) . . . . ?
C21 C12 C16 N6 2.5(15) . . . . ?
C21 C17 C22 C18 -179.9(10) . . . . ?
C22 C17 C21 C12 -81.2(13) . . . . ?
C22 C17 C21 C19 96.8(12) . . . . ?
C23 C15 C18 C22 119.0(12) . . . . ?

_shelx_SHELXL_version_number     2017/1
_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_jmd18ocm
_database_code_depnum_ccdc_archive 'CCDC 1574190'
_audit_update_record             
;
2018-03-25 deposited with the CCDC.
2018-05-08 downloaded from the CCDC.
;
_audit_creation_date             2018-01-20
_audit_creation_method           
;
Olex2 1.2-ac3
(compiled 2016.03.30 svn.r3266 for Rigaku Oxford Diffraction, GUI svn.r5168)
;
_chemical_name_common            ?
_chemical_name_systematic        
;
 ? 
;
_chemical_formula_moiety         'C5 H4 N2 O4, C5 H3 N2 O4, C5 H7 N2'
_chemical_formula_sum            'C15 H14 N6 O8'
_chemical_formula_weight         406.32
_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                   8.705(2)
_cell_length_b                   10.392(3)
_cell_length_c                   10.914(3)
_cell_angle_alpha                65.633(4)
_cell_angle_beta                 76.026(5)
_cell_angle_gamma                70.452(4)
_cell_volume                     841.3(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    673
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      22.08
_cell_measurement_theta_min      2.23
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.133
_exptl_absorpt_correction_T_max  0.982
_exptl_absorpt_correction_T_min  0.839625
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS v.2.10 (Bruker,2003) was used for absorption correction.
R(int) was 0.0488 before and 0.0276 after correction.
The Ratio of minimum to maximum transmission is 0.8396.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.604
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       rod
_exptl_crystal_F_000             420
_exptl_crystal_size_max          .36
_exptl_crystal_size_mid          .28
_exptl_crystal_size_min          .23
_exptl_special_details           
;
 ? 
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0624
_diffrn_reflns_av_unetI/netI     0.0806
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            8190
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        24.999
_diffrn_reflns_theta_max         24.999
_diffrn_reflns_theta_min         2.232
_diffrn_ambient_temperature      298
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1713
_reflns_number_total             2962
_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 v6.45A (Bruker, 2003)'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'SAINT v6.45A (Bruker, 2003)'
_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    'SHELXS-97 (Sheldrick, 1990)'
_refine_diff_density_max         0.230
_refine_diff_density_min         -0.313
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     270
_refine_ls_number_reflns         2962
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1454
_refine_ls_R_factor_gt           0.0795
_refine_ls_restrained_S_all      1.075
_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)+(0.0642P)²+0.1785P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1479
_refine_ls_wR_factor_ref         0.1734
_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
2. Restrained distances
 H2-O2
 0.98 with sigma of 0.02
3.a Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2A), N4(H4), N3(H3A), C3(H3), C6(H6), C12(H12), C14(H14),
 C11(H11), C15(H15)
3.b X=CH2 refined with riding coordinates:
 N6(H6A,H6B)
;
_atom_sites_solution_hydrogens   mixed
_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
O3 O 0.3714(4) -0.0176(3) 0.3883(3) 0.0365(8) Uani 1 1 d . . . . .
O7 O -0.1965(4) 0.5556(3) 0.9500(3) 0.0406(8) Uani 1 1 d . . . . .
O6 O 0.0907(4) 0.9539(3) 0.6763(3) 0.0414(9) Uani 1 1 d . . . . .
N1 N 0.2727(4) 0.1501(3) 0.4899(3) 0.0282(9) Uani 1 1 d . . . . .
H1 H 0.211302 0.096762 0.547938 0.034 Uiso 1 1 calc R . . . .
O2 O 0.6425(4) 0.3872(3) 0.1117(3) 0.0456(9) Uani 1 1 d D . . . .
N2 N 0.3571(4) 0.3613(4) 0.4085(3) 0.0310(9) Uani 1 1 d . . . . .
H2A H 0.354996 0.442269 0.413629 0.037 Uiso 1 1 calc R . . . .
O4 O 0.1743(4) 0.3108(3) 0.5991(3) 0.0386(8) Uani 1 1 d . . . . .
O1 O 0.5266(4) 0.5462(3) 0.2171(3) 0.0535(10) Uani 1 1 d . . . . .
N4 N 0.1738(4) 0.7922(3) 0.5682(3) 0.0309(9) Uani 1 1 d . . . . .
H4 H 0.232274 0.847173 0.508054 0.037 Uiso 1 1 calc R . . . .
N3 N 0.0809(4) 0.5866(3) 0.6466(3) 0.0280(9) Uani 1 1 d . . . . .
H3A H 0.076743 0.508411 0.639516 0.034 Uiso 1 1 calc R . . . .
O8 O -0.1074(4) 0.4157(3) 0.8240(3) 0.0513(10) Uani 1 1 d . . . . .
O5 O 0.2619(4) 0.6367(3) 0.4540(3) 0.0448(9) Uani 1 1 d . . . . .
C9 C -0.0113(5) 0.6225(4) 0.7552(4) 0.0259(10) Uani 1 1 d . . . . .
C1 C 0.5468(5) 0.4321(5) 0.2042(4) 0.0289(10) Uani 1 1 d . . . . .
C2 C 0.4548(5) 0.3227(4) 0.3040(4) 0.0245(10) Uani 1 1 d . . . . .
C3 C 0.4657(5) 0.1957(4) 0.2934(4) 0.0283(10) Uani 1 1 d . . . . .
H3 H 0.534699 0.170049 0.222727 0.034 Uiso 1 1 calc R . . . .
C8 C 0.1786(5) 0.6676(4) 0.5494(4) 0.0286(11) Uani 1 1 d . . . . .
C10 C -0.1128(5) 0.5199(5) 0.8512(4) 0.0290(10) Uani 1 1 d . . . . .
N5 N 0.7669(5) 1.1760(4) -0.1056(4) 0.0485(12) Uani 1 1 d . . . . .
C6 C -0.0086(5) 0.7422(4) 0.7709(4) 0.0260(10) Uani 1 1 d . . . . .
H6 H -0.068424 0.763618 0.846299 0.031 Uiso 1 1 calc R . . . .
C5 C 0.2634(5) 0.2773(4) 0.5044(4) 0.0279(10) Uani 1 1 d . . . . .
C7 C 0.0859(5) 0.8386(4) 0.6724(4) 0.0276(10) Uani 1 1 d . . . . .
C12 C 0.7940(5) 0.9753(5) 0.0995(4) 0.0363(11) Uani 1 1 d . . . . .
H12 H 0.826487 0.931140 0.185921 0.044 Uiso 1 1 calc R . . . .
C14 C 0.6848(5) 0.9717(5) -0.0796(4) 0.0381(12) Uani 1 1 d . . . . .
H14 H 0.641982 0.925994 -0.115753 0.046 Uiso 1 1 calc R . . . .
C13 C 0.7290(5) 0.9011(4) 0.0511(4) 0.0299(11) Uani 1 1 d . . . . .
C4 C 0.3716(5) 0.0996(4) 0.3904(4) 0.0239(10) Uani 1 1 d . . . . .
N6 N 0.7119(5) 0.7678(4) 0.1297(4) 0.0510(11) Uani 1 1 d . . . . .
H6A H 0.672209 0.722137 0.100095 0.061 Uiso 1 1 calc R . . . .
H6B H 0.740479 0.727417 0.210111 0.061 Uiso 1 1 calc R . . . .
C11 C 0.8092(6) 1.1106(5) 0.0205(5) 0.0438(13) Uani 1 1 d . . . . .
H11 H 0.850148 1.159936 0.054050 0.053 Uiso 1 1 calc R . . . .
C15 C 0.7049(5) 1.1082(5) -0.1541(5) 0.0455(13) Uani 1 1 d . . . . .
H15 H 0.674364 1.155367 -0.241163 0.055 Uiso 1 1 calc R . . . .
H5 H 0.789(8) 1.279(7) -0.149(7) 0.14(3) Uiso 1 1 d . . . . .
H2 H 0.709(6) 0.457(5) 0.052(5) 0.11(2) Uiso 1 1 d 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
O3 C4 1.229(4) . ?
O7 C10 1.265(5) . ?
O6 C7 1.230(4) . ?
N1 H1 0.8600 . ?
N1 C5 1.368(5) . ?
N1 C4 1.383(5) . ?
O2 C1 1.286(5) . ?
O2 H2 1.00(2) . ?
N2 H2A 0.8600 . ?
N2 C2 1.366(5) . ?
N2 C5 1.354(5) . ?
O4 C5 1.234(4) . ?
O1 C1 1.201(5) . ?
N4 H4 0.8600 . ?
N4 C8 1.378(5) . ?
N4 C7 1.377(5) . ?
N3 H3A 0.8600 . ?
N3 C9 1.376(5) . ?
N3 C8 1.365(5) . ?
O8 C10 1.220(5) . ?
O5 C8 1.211(4) . ?
C9 C10 1.509(5) . ?
C9 C6 1.332(5) . ?
C1 C2 1.512(5) . ?
C2 C3 1.342(5) . ?
C3 H3 0.9300 . ?
C3 C4 1.430(5) . ?
N5 C11 1.340(6) . ?
N5 C15 1.330(6) . ?
N5 H5 1.04(7) . ?
C6 H6 0.9300 . ?
C6 C7 1.440(5) . ?
C12 H12 0.9300 . ?
C12 C13 1.402(5) . ?
C12 C11 1.344(6) . ?
C14 H14 0.9300 . ?
C14 C13 1.391(6) . ?
C14 C15 1.359(6) . ?
C13 N6 1.331(5) . ?
N6 H6A 0.8600 . ?
N6 H6B 0.8600 . ?
C11 H11 0.9300 . ?
C15 H15 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C5 N1 H1 117.0 . . ?
C5 N1 C4 126.0(3) . . ?
C4 N1 H1 117.0 . . ?
C1 O2 H2 111(3) . . ?
C2 N2 H2A 118.7 . . ?
C5 N2 H2A 118.7 . . ?
C5 N2 C2 122.7(3) . . ?
C8 N4 H4 116.3 . . ?
C7 N4 H4 116.3 . . ?
C7 N4 C8 127.3(3) . . ?
C9 N3 H3A 118.1 . . ?
C8 N3 H3A 118.1 . . ?
C8 N3 C9 123.9(3) . . ?
N3 C9 C10 116.1(3) . . ?
C6 C9 N3 120.4(4) . . ?
C6 C9 C10 123.5(4) . . ?
O2 C1 C2 112.7(4) . . ?
O1 C1 O2 127.2(4) . . ?
O1 C1 C2 120.1(4) . . ?
N2 C2 C1 115.3(3) . . ?
C3 C2 N2 121.0(3) . . ?
C3 C2 C1 123.7(4) . . ?
C2 C3 H3 119.9 . . ?
C2 C3 C4 120.2(4) . . ?
C4 C3 H3 119.9 . . ?
N3 C8 N4 113.5(4) . . ?
O5 C8 N4 121.7(3) . . ?
O5 C8 N3 124.7(4) . . ?
O7 C10 C9 114.8(4) . . ?
O8 C10 O7 127.9(4) . . ?
O8 C10 C9 117.3(4) . . ?
C11 N5 H5 109(4) . . ?
C15 N5 C11 119.9(4) . . ?
C15 N5 H5 131(4) . . ?
C9 C6 H6 119.7 . . ?
C9 C6 C7 120.7(4) . . ?
C7 C6 H6 119.7 . . ?
N2 C5 N1 115.5(4) . . ?
O4 C5 N1 121.1(4) . . ?
O4 C5 N2 123.4(4) . . ?
O6 C7 N4 120.8(4) . . ?
O6 C7 C6 125.0(4) . . ?
N4 C7 C6 114.2(3) . . ?
C13 C12 H12 120.1 . . ?
C11 C12 H12 120.1 . . ?
C11 C12 C13 119.7(4) . . ?
C13 C14 H14 120.3 . . ?
C15 C14 H14 120.3 . . ?
C15 C14 C13 119.4(4) . . ?
C14 C13 C12 117.6(4) . . ?
N6 C13 C12 119.9(4) . . ?
N6 C13 C14 122.5(4) . . ?
O3 C4 N1 120.4(3) . . ?
O3 C4 C3 125.0(4) . . ?
N1 C4 C3 114.6(3) . . ?
C13 N6 H6A 120.0 . . ?
C13 N6 H6B 120.0 . . ?
H6A N6 H6B 120.0 . . ?
N5 C11 C12 121.6(5) . . ?
N5 C11 H11 119.2 . . ?
C12 C11 H11 119.2 . . ?
N5 C15 C14 121.7(5) . . ?
N5 C15 H15 119.1 . . ?
C14 C15 H15 119.1 . . ?

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
N5 H5 O8 1.04(7) 1.81(7) 2.798(5) 156(6) 1_664 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
O2 C1 C2 N2 177.0(4) . . . . ?
O2 C1 C2 C3 -3.1(6) . . . . ?
N2 C2 C3 C4 1.4(6) . . . . ?
O1 C1 C2 N2 -2.7(6) . . . . ?
O1 C1 C2 C3 177.2(4) . . . . ?
N3 C9 C10 O7 -179.9(4) . . . . ?
N3 C9 C10 O8 -1.3(6) . . . . ?
N3 C9 C6 C7 2.2(6) . . . . ?
C9 N3 C8 N4 -1.4(6) . . . . ?
C9 N3 C8 O5 179.2(4) . . . . ?
C9 C6 C7 O6 177.2(4) . . . . ?
C9 C6 C7 N4 -2.3(6) . . . . ?
C1 C2 C3 C4 -178.5(4) . . . . ?
C2 N2 C5 N1 0.0(6) . . . . ?
C2 N2 C5 O4 -179.8(4) . . . . ?
C2 C3 C4 O3 178.9(4) . . . . ?
C2 C3 C4 N1 0.6(6) . . . . ?
C8 N4 C7 O6 -179.0(4) . . . . ?
C8 N4 C7 C6 0.6(6) . . . . ?
C8 N3 C9 C10 179.5(4) . . . . ?
C8 N3 C9 C6 -0.2(6) . . . . ?
C10 C9 C6 C7 -177.5(4) . . . . ?
C6 C9 C10 O7 -0.2(6) . . . . ?
C6 C9 C10 O8 178.4(4) . . . . ?
C5 N1 C4 O3 179.1(4) . . . . ?
C5 N1 C4 C3 -2.5(6) . . . . ?
C5 N2 C2 C1 178.2(4) . . . . ?
C5 N2 C2 C3 -1.7(6) . . . . ?
C7 N4 C8 N3 1.2(6) . . . . ?
C7 N4 C8 O5 -179.4(4) . . . . ?
C13 C12 C11 N5 -1.5(7) . . . . ?
C13 C14 C15 N5 0.5(7) . . . . ?
C4 N1 C5 N2 2.3(6) . . . . ?
C4 N1 C5 O4 -177.9(4) . . . . ?
C11 N5 C15 C14 -1.0(7) . . . . ?
C11 C12 C13 C14 0.9(6) . . . . ?
C11 C12 C13 N6 -179.2(4) . . . . ?
C15 N5 C11 C12 1.5(7) . . . . ?
C15 C14 C13 C12 -0.5(6) . . . . ?
C15 C14 C13 N6 179.7(4) . . . . ?

_shelx_SHELXL_version_number     2017/1
_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_vj220am
_database_code_depnum_ccdc_archive 'CCDC 1574188'
_audit_update_record             
;
2018-03-25 deposited with the CCDC.
2018-05-08 downloaded from the CCDC.
;
_audit_creation_date             2017-10-08
_audit_creation_method           
;
Olex2 1.2-ac3
(compiled 2016.03.30 svn.r3266 for Rigaku Oxford Diffraction, GUI svn.r5168)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C5 H3 N2 O4, C5 H7 N2'
_chemical_formula_sum            'C10 H10 N4 O4'
_chemical_formula_weight         250.22
_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                   12.194(2)
_cell_length_b                   5.1402(10)
_cell_length_c                   17.488(3)
_cell_angle_alpha                90
_cell_angle_beta                 99.377(3)
_cell_angle_gamma                90
_cell_volume                     1081.5(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    571
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      19.16
_cell_measurement_theta_min      2.67
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.122
_exptl_absorpt_correction_T_max  0.980
_exptl_absorpt_correction_T_min  0.795097
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS v.2.10 (Bruker,2003) was used for absorption correction.
R(int) was 0.0451 before and 0.0290 after correction.
The Ratio of minimum to maximum transmission is 0.7951.
The λ/2 correction factor is 0.0015.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.537
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.17
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0900
_diffrn_reflns_av_unetI/netI     0.1112
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            12101
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         28.273
_diffrn_reflns_theta_min         1.693
_diffrn_ambient_temperature      298
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1369
_reflns_number_total             2674
_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 v6.45A (Bruker, 2003)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v6.45A (Bruker, 2003)'
_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    ?
_refine_diff_density_max         0.224
_refine_diff_density_min         -0.228
_refine_diff_density_rms         0.052
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2674
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1667
_refine_ls_R_factor_gt           0.0806
_refine_ls_restrained_S_all      1.010
_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)+(0.0496P)²+0.7910P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1530
_refine_ls_wR_factor_ref         0.1825
_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
2.a Aromatic/amide H refined with riding coordinates:
 N5(H5), N7(H7), C19(H19), N4(H4), C13(H13), C18(H18), C17(H17), C12(H12)
2.b X=CH2 refined with riding coordinates:
 N1(H1A,H1B)
;
_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
N5 N 0.8837(2) 0.2500(5) 0.46377(15) 0.0348(7) Uani 1 1 d . . . . .
H5 H 0.896568 0.377880 0.495698 0.042 Uiso 1 1 calc R . . . .
O3 O 1.05422(18) 0.3097(4) 0.43166(14) 0.0461(7) Uani 1 1 d . . . . .
O1 O 0.9021(2) -0.4442(5) 0.27536(16) 0.0547(7) Uani 1 1 d . . . . .
O2 O 0.7256(2) -0.4570(5) 0.29604(16) 0.0582(8) Uani 1 1 d . . . . .
C6 C 0.9661(3) 0.1902(6) 0.42242(18) 0.0347(8) Uani 1 1 d . . . . .
C2 C 0.8427(3) -0.1458(6) 0.36305(19) 0.0374(8) Uani 1 1 d . . . . .
N7 N 0.9410(2) -0.0134(5) 0.37071(17) 0.0464(8) Uani 1 1 d . . . . .
H7 H 0.989177 -0.058257 0.342327 0.056 Uiso 1 1 calc R . . . .
O4 O 0.7139(2) 0.1979(5) 0.49953(15) 0.0564(7) Uani 1 1 d . . . . .
C1 C 0.8225(3) -0.3706(6) 0.30556(19) 0.0393(9) Uani 1 1 d . . . . .
C19 C 0.7663(3) -0.0805(6) 0.40560(18) 0.0331(8) Uani 1 1 d . . . . .
H19 H 0.700155 -0.174129 0.399623 0.040 Uiso 1 1 calc R . . . .
C4 C 0.7816(3) 0.1276(6) 0.4601(2) 0.0380(8) Uani 1 1 d . . . . .
N1 N 0.8329(2) 0.0973(5) 0.18132(17) 0.0454(8) Uani 1 1 d . . . . .
H1A H 0.851644 0.224276 0.212765 0.054 Uiso 1 1 calc R . . . .
H1B H 0.883076 0.012135 0.162489 0.054 Uiso 1 1 calc R . . . .
N4 N 0.6505(2) 0.1681(5) 0.19189(16) 0.0411(7) Uani 1 1 d . . . . .
H4 H 0.672216 0.292713 0.223548 0.049 Uiso 1 1 calc R . . . .
C15 C 0.7271(3) 0.0330(6) 0.16193(18) 0.0349(8) Uani 1 1 d . . . . .
C13 C 0.5403(3) 0.1176(7) 0.1747(2) 0.0551(10) Uani 1 1 d . . . . .
H13 H 0.490332 0.218123 0.196739 0.066 Uiso 1 1 calc R . . . .
C18 C 0.6891(3) -0.1732(7) 0.1113(2) 0.0466(9) Uani 1 1 d . . . . .
H18 H 0.739741 -0.274174 0.089983 0.056 Uiso 1 1 calc R . . . .
C17 C 0.5795(3) -0.2243(8) 0.0938(2) 0.0557(11) Uani 1 1 d . . . . .
H17 H 0.555015 -0.359343 0.059869 0.067 Uiso 1 1 calc R . . . .
C12 C 0.5024(3) -0.0773(8) 0.1258(2) 0.0609(12) Uani 1 1 d . . . . .
H12 H 0.426747 -0.112636 0.113776 0.073 Uiso 1 1 calc R . . . .


_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
N5 H5 0.8600 . ?
N5 C6 1.365(4) . ?
N5 C4 1.387(4) . ?
O3 C6 1.225(4) . ?
O1 C1 1.238(4) . ?
O2 C1 1.248(4) . ?
C6 N7 1.384(4) . ?
C2 N7 1.366(4) . ?
C2 C1 1.525(4) . ?
C2 C19 1.327(4) . ?
N7 H7 0.8600 . ?
O4 C4 1.215(4) . ?
C19 H19 0.9300 . ?
C19 C4 1.424(4) . ?
N1 H1A 0.8600 . ?
N1 H1B 0.8600 . ?
N1 C15 1.322(4) . ?
N4 H4 0.8600 . ?
N4 C15 1.337(4) . ?
N4 C13 1.353(4) . ?
C15 C18 1.410(5) . ?
C13 H13 0.9300 . ?
C13 C12 1.349(5) . ?
C18 H18 0.9300 . ?
C18 C17 1.347(5) . ?
C17 H17 0.9300 . ?
C17 C12 1.392(5) . ?
C12 H12 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 N5 H5 116.4 . . ?
C6 N5 C4 127.2(3) . . ?
C4 N5 H5 116.4 . . ?
N5 C6 N7 114.4(3) . . ?
O3 C6 N5 121.5(3) . . ?
O3 C6 N7 124.1(3) . . ?
N7 C2 C1 119.2(3) . . ?
C19 C2 N7 120.3(3) . . ?
C19 C2 C1 120.5(3) . . ?
C6 N7 H7 118.7 . . ?
C2 N7 C6 122.5(3) . . ?
C2 N7 H7 118.7 . . ?
O1 C1 O2 128.8(3) . . ?
O1 C1 C2 117.3(3) . . ?
O2 C1 C2 113.9(3) . . ?
C2 C19 H19 118.8 . . ?
C2 C19 C4 122.5(3) . . ?
C4 C19 H19 118.8 . . ?
N5 C4 C19 113.1(3) . . ?
O4 C4 N5 121.8(3) . . ?
O4 C4 C19 125.2(3) . . ?
H1A N1 H1B 120.0 . . ?
C15 N1 H1A 120.0 . . ?
C15 N1 H1B 120.0 . . ?
C15 N4 H4 118.5 . . ?
C15 N4 C13 123.0(3) . . ?
C13 N4 H4 118.5 . . ?
N1 C15 N4 119.0(3) . . ?
N1 C15 C18 123.8(3) . . ?
N4 C15 C18 117.2(3) . . ?
N4 C13 H13 119.7 . . ?
C12 C13 N4 120.6(4) . . ?
C12 C13 H13 119.7 . . ?
C15 C18 H18 119.9 . . ?
C17 C18 C15 120.1(4) . . ?
C17 C18 H18 119.9 . . ?
C18 C17 H17 119.6 . . ?
C18 C17 C12 120.8(3) . . ?
C12 C17 H17 119.6 . . ?
C13 C12 C17 118.2(4) . . ?
C13 C12 H12 120.9 . . ?
C17 C12 H12 120.9 . . ?

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
N5 C6 N7 C2 -1.2(4) . . . . ?
O3 C6 N7 C2 178.6(3) . . . . ?
C6 N5 C4 O4 -179.7(3) . . . . ?
C6 N5 C4 C19 -0.4(4) . . . . ?
C2 C19 C4 N5 -0.4(5) . . . . ?
C2 C19 C4 O4 178.8(3) . . . . ?
N7 C2 C1 O1 8.9(5) . . . . ?
N7 C2 C1 O2 -171.6(3) . . . . ?
N7 C2 C19 C4 0.4(5) . . . . ?
C1 C2 N7 C6 -179.0(3) . . . . ?
C1 C2 C19 C4 179.9(3) . . . . ?
C19 C2 N7 C6 0.4(5) . . . . ?
C19 C2 C1 O1 -170.6(3) . . . . ?
C19 C2 C1 O2 8.9(5) . . . . ?
C4 N5 C6 O3 -178.6(3) . . . . ?
C4 N5 C6 N7 1.2(4) . . . . ?
N1 C15 C18 C17 -179.2(3) . . . . ?
N4 C15 C18 C17 1.2(5) . . . . ?
N4 C13 C12 C17 0.0(6) . . . . ?
C15 N4 C13 C12 0.5(6) . . . . ?
C15 C18 C17 C12 -0.7(6) . . . . ?
C13 N4 C15 N1 179.3(3) . . . . ?
C13 N4 C15 C18 -1.1(5) . . . . ?
C18 C17 C12 C13 0.1(6) . . . . ?

_shelx_SHELXL_version_number     2017/1
_olex2_submission_special_instructions 'No special instructions were received'
