# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_xstr0044
_database_code_depnum_ccdc_archive 'CCDC 1034270'
_audit_update_record             
;
2014-11-14 deposited with the CCDC.
2015-02-02 downloaded from the CCDC.
;
_audit_creation_date             2013-09-30
_audit_creation_method           
;
Olex2 1.2
(compiled 2013.09.17 svn.r2790 for OlexSys, GUI svn.r4601)
;
_shelxl_version_number           2013-4
_chemical_name_common            ?
_chemical_name_systematic        azepinomycin
_chemical_formula_moiety         'C6 H8 N4 O2'
_chemical_formula_sum            'C6 H8 N4 O2'
_chemical_formula_weight         168.16
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C6 H8 N4 O2'
_chemical_oxdiff_usercomment     'AC (powner) DAT 27-9-13'
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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'

_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                   6.68948(7)
_cell_length_b                   14.04389(15)
_cell_length_c                   7.22458(9)
_cell_angle_alpha                90
_cell_angle_beta                 93.8750(11)
_cell_angle_gamma                90
_cell_volume                     677.171(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    8155
_cell_measurement_temperature    150
_cell_measurement_theta_max      73.3580
_cell_measurement_theta_min      6.1050
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.090
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83086
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   ?
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.649
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             352
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: water'
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.15
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0198
_diffrn_reflns_av_unetI/netI     0.0092
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.970
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_number            9206
_diffrn_reflns_point_group_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.970
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         73.672
_diffrn_reflns_theta_min         6.303
_diffrn_ambient_temperature      150
_diffrn_detector_area_resol_mean 5.2031
_diffrn_measured_fraction_theta_full 0.9936
_diffrn_measured_fraction_theta_max 0.9875
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -37.00   -9.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.5651  -77.0000  -60.0000 28

#__ type_ start__ end____ width___ exp.time_
  2 omega  -44.00   -8.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.5651  -77.0000   30.0000 36

#__ type_ start__ end____ width___ exp.time_
  3 omega  -50.00   34.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.5651   38.0000    0.0000 84

#__ type_ start__ end____ width___ exp.time_
  4 omega -119.00  -75.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.5651  -77.0000   30.0000 44

#__ type_ start__ end____ width___ exp.time_
  5 omega -100.00  -61.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.5651  -77.0000 -150.0000 39

#__ type_ start__ end____ width___ exp.time_
  6 omega  -37.00   -9.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.5651  -77.0000   90.0000 28

#__ type_ start__ end____ width___ exp.time_
  7 omega  -50.00   19.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.5651   38.0000 -180.0000 69

#__ type_ start__ end____ width___ exp.time_
  8 omega -106.00  -71.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.5651  -77.0000   90.0000 35

#__ type_ start__ end____ width___ exp.time_
  9 omega  -54.00   -8.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -41.5651  -77.0000 -150.0000 46

#__ type_ start__ end____ width___ exp.time_
 10 omega   20.00   51.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -       41.5651   38.0000  120.0000 31

#__ type_ start__ end____ width___ exp.time_
 11 omega  -96.00   -3.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -61.5000  125.0000    0.0000 93

#__ type_ start__ end____ width___ exp.time_
 12 omega  -56.00  -30.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -61.5000  -77.0000  -60.0000 26

#__ type_ start__ end____ width___ exp.time_
 13 omega  -68.00  -29.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -61.5000  -77.0000    0.0000 39

#__ type_ start__ end____ width___ exp.time_
 14 omega  -56.00  -30.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -61.5000  -77.0000 -150.0000 26

#__ type_ start__ end____ width___ exp.time_
 15 omega  -62.00  -29.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -61.5000  -77.0000 -180.0000 33

#__ type_ start__ end____ width___ exp.time_
 16 omega  -69.00  -29.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -61.5000  -77.0000   60.0000 40

#__ type_ start__ end____ width___ exp.time_
 17 omega  -55.00   12.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -61.5000   45.0000  -90.0000 67

#__ type_ start__ end____ width___ exp.time_
 18 omega  -68.00  -28.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -61.5000  -77.0000  120.0000 40

#__ type_ start__ end____ width___ exp.time_
 19 omega -100.00  -35.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      -61.5000  -77.0000  -90.0000 65

#__ type_ start__ end____ width___ exp.time_
 20 omega   74.00  162.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.4180   77.0000   90.0000 88

#__ type_ start__ end____ width___ exp.time_
 21 omega   80.00  172.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.4180   61.0000   30.0000 92

#__ type_ start__ end____ width___ exp.time_
 22 omega   33.00   77.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.4180  -45.0000  150.0000 44

#__ type_ start__ end____ width___ exp.time_
 23 omega   74.00  132.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.4180   77.0000   60.0000 58

#__ type_ start__ end____ width___ exp.time_
 24 omega   76.00  178.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.4180   77.0000 -180.0000 102

#__ type_ start__ end____ width___ exp.time_
 25 omega   80.00  108.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.4180   61.0000  -30.0000 28

#__ type_ start__ end____ width___ exp.time_
 26 omega  117.00  175.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.4180   61.0000  -60.0000 58

#__ type_ start__ end____ width___ exp.time_
 27 omega   24.00  107.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.4180  -95.0000   30.0000 83

#__ type_ start__ end____ width___ exp.time_
 28 omega   74.00  170.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.4180   77.0000 -120.0000 96

#__ type_ start__ end____ width___ exp.time_
 29 omega   78.00  140.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.4180   77.0000  150.0000 62

#__ type_ start__ end____ width___ exp.time_
 30 omega   74.00  100.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.4180   77.0000  120.0000 26

#__ type_ start__ end____ width___ exp.time_
 31 omega   83.00  115.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.4180   61.0000  -60.0000 32

#__ type_ start__ end____ width___ exp.time_
 32 omega   34.00   89.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.4180  -45.0000  -90.0000 55

#__ type_ start__ end____ width___ exp.time_
 33 omega   83.00  109.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.4180   45.0000  -30.0000 26

#__ type_ start__ end____ width___ exp.time_
 34 omega   32.00  116.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.4180 -125.0000  -30.0000 84

#__ type_ start__ end____ width___ exp.time_
 35 omega   74.00  100.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.4180   77.0000    0.0000 26

#__ type_ start__ end____ width___ exp.time_
 36 omega   74.00  100.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.4180   77.0000  -90.0000 26

#__ type_ start__ end____ width___ exp.time_
 37 omega   74.00  127.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.4180   77.0000 -150.0000 53

#__ type_ start__ end____ width___ exp.time_
 38 omega   81.00  137.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.4180   61.0000  150.0000 56

#__ type_ start__ end____ width___ exp.time_
 39 omega  134.00  169.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.4180  125.0000    0.0000 35

#__ type_ start__ end____ width___ exp.time_
 40 omega   80.00  138.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.4180   61.0000    0.0000 58

#__ type_ start__ end____ width___ exp.time_
 41 omega   78.00  103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.4180   61.0000 -150.0000 25

#__ type_ start__ end____ width___ exp.time_
 42 omega   77.00  103.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.4180   61.0000   60.0000 26

#__ type_ start__ end____ width___ exp.time_
 43 omega   30.00  110.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.4180  -95.0000  150.0000 80

#__ type_ start__ end____ width___ exp.time_
 44 omega  108.00  133.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.4180   70.0000  118.1129 25

#__ type_ start__ end____ width___ exp.time_
 45 omega  107.00  174.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.4180  125.0000 -150.0000 67

#__ type_ start__ end____ width___ exp.time_
 46 omega   75.00  101.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -      107.4180   70.0000  118.1129 26
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.1776708000
_diffrn_orient_matrix_UB_12      0.0234663000
_diffrn_orient_matrix_UB_13      -0.1171613000
_diffrn_orient_matrix_UB_21      0.0870981000
_diffrn_orient_matrix_UB_22      -0.1000904000
_diffrn_orient_matrix_UB_23      0.0392542000
_diffrn_orient_matrix_UB_31      -0.1188257000
_diffrn_orient_matrix_UB_32      -0.0382924000
_diffrn_orient_matrix_UB_33      -0.1743843000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.5418
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1294
_reflns_number_total             1328
_reflns_odcompleteness_completeness 99.36
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.49
_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       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_publication_material  
;
O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann,
OLEX2: a complete structure solution, refinement and analysis program.
J. Appl. Cryst. (2009). 42, 339-341.
;
_computing_structure_refinement  
;
SHELX, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_computing_structure_solution    
;
SHELX, G.M. Sheldrick, Acta Cryst.
(2008). A64, 112-122
;
_refine_diff_density_max         0.695
_refine_diff_density_min         -0.664
_refine_diff_density_rms         0.054
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     110
_refine_ls_number_reflns         1328
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0389
_refine_ls_R_factor_gt           0.0383
_refine_ls_restrained_S_all      1.088
_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)+(0.0545P)²+0.4643P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1004
_refine_ls_wR_factor_ref         0.1007
_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 Ternary CH refined with riding coordinates:
 C2(H2B)
2.b Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B)
2.c Aromatic/amide H refined with riding coordinates:
 N1(H1), N2(H2A), N4(H4), C5(H5)
2.d Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_atom_sites_solution_hydrogens   geom
_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
O1 O 1.31867(15) 0.51529(7) 0.18218(14) 0.0169(3) Uani 1 1 d . . . . .
O2 O 0.71937(14) 0.61521(7) 0.08532(13) 0.0129(2) Uani 1 1 d . . . . .
H2 H 0.7028 0.5748 -0.0001 0.019 Uiso 1 1 calc R U . . .
N1 N 0.98711(17) 0.52304(8) 0.22596(16) 0.0142(3) Uani 1 1 d . . . . .
H1 H 0.9838 0.4606 0.2161 0.017 Uiso 1 1 calc R U . . .
N2 N 0.87653(17) 0.73457(8) 0.35428(16) 0.0137(3) Uani 1 1 d . . . . .
H2A H 0.8003 0.7856 0.3568 0.016 Uiso 1 1 calc R U . . .
N3 N 1.16406(18) 0.82512(8) 0.28871(16) 0.0142(3) Uani 1 1 d . . . . .
N4 N 1.36666(17) 0.71083(9) 0.20225(16) 0.0139(3) Uani 1 1 d . . . . .
H4 H 1.4745 0.6829 0.1646 0.017 Uiso 1 1 calc R U . . .
C1 C 1.1684(2) 0.56422(10) 0.21644(18) 0.0127(3) Uani 1 1 d . . . . .
C2 C 0.7974(2) 0.56938(9) 0.25048(19) 0.0131(3) Uani 1 1 d . . . . .
H2B H 0.6998 0.5187 0.2809 0.016 Uiso 1 1 calc R U . . .
C3 C 0.8043(2) 0.64220(10) 0.40878(19) 0.0146(3) Uani 1 1 d . . . . .
H3A H 0.6681 0.6495 0.4526 0.017 Uiso 1 1 calc R U . . .
H3B H 0.8926 0.6177 0.5136 0.017 Uiso 1 1 calc R U . . .
C4 C 1.0677(2) 0.73954(9) 0.29876(18) 0.0120(3) Uani 1 1 d . . . . .
C5 C 1.3429(2) 0.80395(10) 0.22966(19) 0.0147(3) Uani 1 1 d . . . . .
H5 H 1.4428 0.8501 0.2092 0.018 Uiso 1 1 calc R U . . .
C6 C 1.1900(2) 0.66590(10) 0.24407(19) 0.0127(3) 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
O1 C1 1.2558(17) . ?
O2 C2 1.4235(16) . ?
N1 C1 1.3498(18) . ?
N1 C2 1.4477(17) . ?
N2 C3 1.4482(18) . ?
N2 C4 1.3678(18) . ?
N3 C4 1.3680(18) . ?
N3 C5 1.3307(18) . ?
N4 C5 1.3338(19) . ?
N4 C6 1.3909(17) . ?
C1 C6 1.4477(19) . ?
C2 C3 1.5326(19) . ?
C4 C6 1.3922(18) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C2 127.73(11) . . ?
C4 N2 C3 117.48(11) . . ?
C5 N3 C4 104.93(11) . . ?
C5 N4 C6 107.52(11) . . ?
O1 C1 N1 120.63(12) . . ?
O1 C1 C6 119.56(12) . . ?
N1 C1 C6 119.80(12) . . ?
O2 C2 N1 112.05(11) . . ?
O2 C2 C3 108.33(10) . . ?
N1 C2 C3 114.13(11) . . ?
N2 C3 C2 112.87(11) . . ?
N2 C4 N3 120.91(12) . . ?
N2 C4 C6 128.62(13) . . ?
N3 C4 C6 110.47(12) . . ?
N3 C5 N4 112.67(12) . . ?
N4 C6 C1 119.71(12) . . ?
N4 C6 C4 104.40(12) . . ?
C4 C6 C1 135.80(13) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C6 N4 10.74(19) . . . . ?
O1 C1 C6 C4 -173.09(15) . . . . ?
O2 C2 C3 N2 -42.48(15) . . . . ?
N1 C1 C6 N4 -168.63(12) . . . . ?
N1 C1 C6 C4 7.5(2) . . . . ?
N1 C2 C3 N2 83.10(14) . . . . ?
N2 C4 C6 N4 179.83(13) . . . . ?
N2 C4 C6 C1 3.3(3) . . . . ?
N3 C4 C6 N4 0.68(15) . . . . ?
N3 C4 C6 C1 -175.88(15) . . . . ?
C1 N1 C2 O2 75.27(17) . . . . ?
C1 N1 C2 C3 -48.33(18) . . . . ?
C2 N1 C1 O1 -175.15(12) . . . . ?
C2 N1 C1 C6 4.2(2) . . . . ?
C3 N2 C4 N3 -163.94(12) . . . . ?
C3 N2 C4 C6 17.0(2) . . . . ?
C4 N2 C3 C2 -62.10(16) . . . . ?
C4 N3 C5 N4 -0.22(16) . . . . ?
C5 N3 C4 N2 -179.54(12) . . . . ?
C5 N3 C4 C6 -0.31(16) . . . . ?
C5 N4 C6 C1 176.46(12) . . . . ?
C5 N4 C6 C4 -0.78(14) . . . . ?
C6 N4 C5 N3 0.65(16) . . . . ?

