data_udlafunm
_audit_creation_date              2018-11-19
_audit_creation_method
;
Olex2 1.2
(compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998)
;
_publ_contact_author_address      ?
_publ_contact_author_email        ?
_publ_contact_author_name         ''
_publ_contact_author_phone        ?
_publ_section_references
;
Dolomanov, O.V., Bourhis, L.J., Gildea, R.J, Howard, J.A.K. & Puschmann, H.
 (2009), J. Appl. Cryst. 42, 339-341.

Sheldrick, G.M. (2008). Acta Cryst. A64, 112-122.

Sheldrick, G.M. (2015). Acta Cryst. A71, 3-8.
;
_chemical_name_common             ?
_chemical_name_systematic         ?
_chemical_formula_moiety          'C22 H26 N4 O6, 2(H2 O)'
_chemical_formula_sum             'C22 H30 N4 O8'
_chemical_formula_weight          478.50
_chemical_absolute_configuration  unk
_chemical_melting_point           ?
loop_
  _atom_type_symbol
  _atom_type_description
  _atom_type_scat_dispersion_real
  _atom_type_scat_dispersion_imag
  _atom_type_scat_source
 'C' 'C' 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'H' 'H' 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'N' 'N' 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
 'O' 'O' 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system       'orthorhombic'
_space_group_IT_number            19
_space_group_name_H-M_alt         'P 21 21 21'
_space_group_name_Hall            'P 2ac 2ab'
loop_
  _space_group_symop_operation_xyz
 'x, y, z'
 '-x+1/2, -y, z+1/2'
 '-x, y+1/2, -z+1/2'
 'x+1/2, -y+1/2, -z'

_cell_length_a                    7.3272(5)
_cell_length_b                    13.6323(10)
_cell_length_c                    23.8535(18)
_cell_angle_alpha                 90
_cell_angle_beta                  90
_cell_angle_gamma                 90
_cell_volume                      2382.6(3)
_cell_formula_units_Z             4
_cell_measurement_reflns_used     6933
_cell_measurement_temperature     293.15
_cell_measurement_theta_max       23.57
_cell_measurement_theta_min       2.27
_shelx_estimated_absorpt_T_max    ?
_shelx_estimated_absorpt_T_min    ?
_exptl_absorpt_coefficient_mu     0.102
_exptl_absorpt_correction_T_max   1.00
_exptl_absorpt_correction_T_min   0.90
_exptl_absorpt_correction_type    multi-scan
_exptl_absorpt_process_details    
;
SADABS was used for absorption correction.
;
_exptl_crystal_colour             colourless
_exptl_crystal_colour_primary     colourless
_exptl_crystal_density_diffrn     1.334
_exptl_crystal_density_meas       .
_exptl_crystal_density_method     ?
_exptl_crystal_description        prism
_exptl_crystal_F_000              1016
_exptl_crystal_size_max           0.51
_exptl_crystal_size_mid           0.18
_exptl_crystal_size_min           0.14
_exptl_transmission_factor_max    ?
_exptl_transmission_factor_min    ?
_diffrn_reflns_av_R_equivalents   0.0594
_diffrn_reflns_av_unetI/netI      0.0465
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max        8
_diffrn_reflns_limit_h_min        -8
_diffrn_reflns_limit_k_max        16
_diffrn_reflns_limit_k_min        -16
_diffrn_reflns_limit_l_max        28
_diffrn_reflns_limit_l_min        -28
_diffrn_reflns_number             23962
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full         25.242
_diffrn_reflns_theta_max          25.495
_diffrn_reflns_theta_min          1.707
_diffrn_ambient_temperature       293.15
_diffrn_detector_area_resol_mean  ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type   'Bruker APEX'
_diffrn_measurement_method        ?
_diffrn_radiation_monochromator   'graphite'
_diffrn_radiation_type            MoK\a
_diffrn_radiation_wavelength      0.71073
_diffrn_source                    ?
_reflns_Friedel_coverage          0.740
_reflns_Friedel_fraction_full     0.999
_reflns_Friedel_fraction_max      0.999
_reflns_number_gt                 4009
_reflns_number_total              4439
_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        'Bruker SAINT version 6.01 and 6.04'
_computing_data_collection        'Bruker SMART'
_computing_data_reduction         'Bruker SAINT version 6.01 and 6.04'
_computing_molecular_graphics     'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material   'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement   'ShelXL (Sheldrick, 2008)'
_computing_structure_solution     'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max          0.203
_refine_diff_density_min          -0.206
_refine_diff_density_rms          0.044
_refine_ls_abs_structure_details
;
 Flack x determined using 1212 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack    ?
_refine_ls_extinction_coef        .
_refine_ls_extinction_method      none
_refine_ls_goodness_of_fit_ref    1.274
_refine_ls_hydrogen_treatment     constr
_refine_ls_matrix_type            full
_refine_ls_number_parameters      314
_refine_ls_number_reflns          4439
_refine_ls_number_restraints      0
_refine_ls_R_factor_all           0.0875
_refine_ls_R_factor_gt            0.0778
_refine_ls_restrained_S_all       1.274
_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)+(0.0471P)²+0.6912P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme       calc
_refine_ls_wR_factor_gt           0.1429
_refine_ls_wR_factor_ref          0.1468
_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, All O(H,H) groups
2.a Free rotating group:
 O31(H31A,H31B), O32(H32A,H32B)
2.b Ternary CH refined with riding coordinates:
 N2(H2)
2.c Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C3(H3A,H3B), C4(H4B,H4C), C5(H5A,H5B), C7(H7A,H7B), C9(H9A,H9B)
2.d Aromatic/amide H refined with riding coordinates:
 N3(H3), N4(H4), C12(H12), C13(H13), C14(H14), C15(H15), C16(H16), C18(H18),
 C19(H19), C20(H20), C21(H21), C22(H22)
2.e Idealised tetrahedral OH refined as rotating group:
 O4(H4A)
;
_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
 N1 N 0.6050(5) 0.0385(3) 0.32887(16) 0.0365(10) Uani 1 1 d . . . . .
 N2 N 0.4299(5) 0.1417(3) 0.23839(16) 0.0332(9) Uani 1 1 d . . . . .
 H2 H 0.5014 0.1679 0.2697 0.040 Uiso 1 1 calc R . . . .
 N3 N 0.2717(6) 0.0270(3) 0.43757(17) 0.0475(11) Uani 1 1 d . . . . .
 H3 H 0.3188 -0.0263 0.4504 0.057 Uiso 1 1 calc R . . . .
 N4 N 0.0455(5) 0.2800(3) 0.29500(19) 0.0421(11) Uani 1 1 d . . . . .
 H4 H -0.0354 0.2413 0.2811 0.051 Uiso 1 1 calc R . . . .
 O1 O 0.3182(7) 0.1471(3) 0.37458(18) 0.0819(15) Uani 1 1 d . . . . .
 O2 O 0.3505(4) 0.3097(3) 0.29009(15) 0.0430(9) Uani 1 1 d . . . . .
 O3 O 0.7926(5) -0.1441(3) 0.35027(16) 0.0482(9) Uani 1 1 d . . . . .
 O4 O 1.0528(4) -0.0780(3) 0.32421(18) 0.0535(11) Uani 1 1 d . . . . .
 H4A H 1.0908 -0.1337 0.3301 0.080 Uiso 1 1 calc GR . . . .
 O5 O 0.7763(5) 0.1901(3) 0.23176(16) 0.0566(11) Uani 1 1 d . . . . .
 O6 O 0.7584(5) 0.2662(3) 0.14992(16) 0.0560(11) Uani 1 1 d . . . . .
 C1 C 0.3680(8) 0.0742(4) 0.3982(2) 0.0508(15) Uani 1 1 d . . . . .
 C2 C 0.5527(8) 0.0282(5) 0.3872(2) 0.0548(15) Uani 1 1 d . . . . .
 H2A H 0.6437 0.0594 0.4107 0.066 Uiso 1 1 calc R . . . .
 H2B H 0.5485 -0.0408 0.3969 0.066 Uiso 1 1 calc R . . . .
 C3 C 0.4846(6) -0.0139(3) 0.2907(2) 0.0367(11) Uani 1 1 d . . . . .
 H3A H 0.3634 -0.0171 0.3070 0.044 Uiso 1 1 calc R . . . .
 H3B H 0.5287 -0.0805 0.2861 0.044 Uiso 1 1 calc R . . . .
 C4 C 0.4734(7) 0.0345(3) 0.2345(2) 0.0366(11) Uani 1 1 d . . . . .
 H4B H 0.3801 0.0021 0.2124 0.044 Uiso 1 1 calc R . . . .
 H4C H 0.5891 0.0263 0.2153 0.044 Uiso 1 1 calc R . . . .
 C5 C 0.2355(6) 0.1618(3) 0.2512(2) 0.0356(11) Uani 1 1 d . . . . .
 H5A H 0.1874 0.1103 0.2750 0.043 Uiso 1 1 calc R . . . .
 H5B H 0.1654 0.1625 0.2167 0.043 Uiso 1 1 calc R . . . .
 C6 C 0.2170(6) 0.2601(4) 0.28056(19) 0.0338(11) Uani 1 1 d . . . . .
 C7 C 0.7984(7) 0.0242(4) 0.3194(2) 0.0411(12) Uani 1 1 d . . . . .
 H7A H 0.8639 0.0730 0.3410 0.049 Uiso 1 1 calc R . . . .
 H7B H 0.8230 0.0373 0.2801 0.049 Uiso 1 1 calc R . . . .
 C8 C 0.8774(7) -0.0752(4) 0.3334(2) 0.0380(12) Uani 1 1 d . . . . .
 C9 C 0.4913(6) 0.1947(4) 0.1871(2) 0.0380(12) Uani 1 1 d . . . . .
 H9A H 0.4230 0.2552 0.1833 0.046 Uiso 1 1 calc R . . . .
 H9B H 0.4670 0.1546 0.1543 0.046 Uiso 1 1 calc R . . . .
 C10 C 0.6952(7) 0.2179(4) 0.1900(2) 0.0382(12) Uani 1 1 d . . . . .
 C11 C 0.1005(7) 0.0549(4) 0.4606(2) 0.0431(13) Uani 1 1 d . . . . .
 C12 C 0.0011(9) -0.0154(5) 0.4879(2) 0.0581(16) Uani 1 1 d . . . . .
 H12 H 0.0424 -0.0799 0.4885 0.070 Uiso 1 1 calc R . . . .
 C13 C -0.1594(9) 0.0083(6) 0.5146(3) 0.0698(19) Uani 1 1 d . . . . .
 H13 H -0.2245 -0.0397 0.5338 0.084 Uiso 1 1 calc R . . . .
 C14 C -0.2234(10) 0.1029(6) 0.5130(3) 0.073(2) Uani 1 1 d . . . . .
 H14 H -0.3323 0.1193 0.5306 0.088 Uiso 1 1 calc R . . . .
 C15 C -0.1245(10) 0.1729(5) 0.4850(3) 0.0680(19) Uani 1 1 d . . . . .
 H15 H -0.1661 0.2373 0.4842 0.082 Uiso 1 1 calc R . . . .
 C16 C 0.0348(8) 0.1493(5) 0.4581(2) 0.0568(16) Uani 1 1 d . . . . .
 H16 H 0.0983 0.1970 0.4382 0.068 Uiso 1 1 calc R . . . .
 C17 C -0.0231(7) 0.3555(4) 0.3298(2) 0.0383(12) Uani 1 1 d . . . . .
 C18 C -0.1929(8) 0.3423(4) 0.3528(2) 0.0546(15) Uani 1 1 d . . . . .
 H18 H -0.2577 0.2851 0.3454 0.065 Uiso 1 1 calc R . . . .
 C19 C -0.2679(10) 0.4131(5) 0.3867(3) 0.0662(18) Uani 1 1 d . . . . .
 H19 H -0.3822 0.4030 0.4026 0.079 Uiso 1 1 calc R . . . .
 C20 C -0.1761(10) 0.4979(5) 0.3970(2) 0.0637(19) Uani 1 1 d . . . . .
 H20 H -0.2265 0.5459 0.4200 0.076 Uiso 1 1 calc R . . . .
 C21 C -0.0093(10) 0.5112(5) 0.3732(2) 0.0645(18) Uani 1 1 d . . . . .
 H21 H 0.0527 0.5697 0.3795 0.077 Uiso 1 1 calc R . . . .
 C22 C 0.0697(9) 0.4411(4) 0.3404(2) 0.0545(15) Uani 1 1 d . . . . .
 H22 H 0.1853 0.4511 0.3253 0.065 Uiso 1 1 calc R . . . .
 O31 O 0.1174(7) 0.1811(3) 0.95361(18) 0.0707(13) Uani 1 1 d . . . . .
 H31A H 0.1524 0.2109 0.9242 0.106 Uiso 1 1 d G . . . .
 H31B H 0.1651 0.2079 0.9822 0.106 Uiso 1 1 d G . . . .
 O32 O 0.7686(8) 0.2545(4) 0.9504(2) 0.0882(16) Uani 1 1 d . . . . .
 H32A H 0.8657 0.2223 0.9568 0.132 Uiso 1 1 d G . . . .
 H32B H 0.7086 0.2267 0.9244 0.132 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
 N1 C2 1.449(6) . ?
 N1 C3 1.455(6) . ?
 N1 C7 1.448(6) . ?
 N2 H2 0.9800 . ?
 N2 C4 1.499(6) . ?
 N2 C5 1.482(6) . ?
 N2 C9 1.490(6) . ?
 N3 H3 0.8600 . ?
 N3 C1 1.340(7) . ?
 N3 C11 1.421(7) . ?
 N4 H4 0.8600 . ?
 N4 C6 1.331(6) . ?
 N4 C17 1.416(6) . ?
 O1 C1 1.198(6) . ?
 O2 C6 1.212(5) . ?
 O3 C8 1.196(6) . ?
 O4 H4A 0.8200 . ?
 O4 C8 1.305(6) . ?
 O5 C10 1.220(6) . ?
 O6 C10 1.250(6) . ?
 C1 C2 1.514(8) . ?
 C2 H2A 0.9700 . ?
 C2 H2B 0.9700 . ?
 C3 H3A 0.9700 . ?
 C3 H3B 0.9700 . ?
 C3 C4 1.496(7) . ?
 C4 H4B 0.9700 . ?
 C4 H4C 0.9700 . ?
 C5 H5A 0.9700 . ?
 C5 H5B 0.9700 . ?
 C5 C6 1.517(7) . ?
 C7 H7A 0.9700 . ?
 C7 H7B 0.9700 . ?
 C7 C8 1.511(7) . ?
 C9 H9A 0.9700 . ?
 C9 H9B 0.9700 . ?
 C9 C10 1.529(7) . ?
 C11 C12 1.369(8) . ?
 C11 C16 1.375(8) . ?
 C12 H12 0.9300 . ?
 C12 C13 1.375(9) . ?
 C13 H13 0.9300 . ?
 C13 C14 1.372(9) . ?
 C14 H14 0.9300 . ?
 C14 C15 1.371(9) . ?
 C15 H15 0.9300 . ?
 C15 C16 1.370(9) . ?
 C16 H16 0.9300 . ?
 C17 C18 1.371(7) . ?
 C17 C22 1.374(8) . ?
 C18 H18 0.9300 . ?
 C18 C19 1.374(8) . ?
 C19 H19 0.9300 . ?
 C19 C20 1.360(9) . ?
 C20 H20 0.9300 . ?
 C20 C21 1.360(9) . ?
 C21 H21 0.9300 . ?
 C21 C22 1.365(8) . ?
 C22 H22 0.9300 . ?
 O31 H31A 0.8508 . ?
 O31 H31B 0.8494 . ?
 O32 H32A 0.8497 . ?
 O32 H32B 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 N1 C3 113.1(4) . . ?
 C7 N1 C2 113.3(4) . . ?
 C7 N1 C3 115.4(4) . . ?
 C4 N2 H2 106.8 . . ?
 C5 N2 H2 106.8 . . ?
 C5 N2 C4 113.4(4) . . ?
 C5 N2 C9 111.7(4) . . ?
 C9 N2 H2 106.8 . . ?
 C9 N2 C4 111.0(4) . . ?
 C1 N3 H3 116.3 . . ?
 C1 N3 C11 127.4(5) . . ?
 C11 N3 H3 116.3 . . ?
 C6 N4 H4 115.2 . . ?
 C6 N4 C17 129.5(4) . . ?
 C17 N4 H4 115.2 . . ?
 C8 O4 H4A 109.5 . . ?
 N3 C1 C2 113.2(5) . . ?
 O1 C1 N3 124.5(5) . . ?
 O1 C1 C2 122.3(6) . . ?
 N1 C2 C1 111.3(5) . . ?
 N1 C2 H2A 109.4 . . ?
 N1 C2 H2B 109.4 . . ?
 C1 C2 H2A 109.4 . . ?
 C1 C2 H2B 109.4 . . ?
 H2A C2 H2B 108.0 . . ?
 N1 C3 H3A 109.2 . . ?
 N1 C3 H3B 109.2 . . ?
 N1 C3 C4 112.2(4) . . ?
 H3A C3 H3B 107.9 . . ?
 C4 C3 H3A 109.2 . . ?
 C4 C3 H3B 109.2 . . ?
 N2 C4 H4B 109.1 . . ?
 N2 C4 H4C 109.1 . . ?
 C3 C4 N2 112.7(4) . . ?
 C3 C4 H4B 109.1 . . ?
 C3 C4 H4C 109.1 . . ?
 H4B C4 H4C 107.8 . . ?
 N2 C5 H5A 109.6 . . ?
 N2 C5 H5B 109.6 . . ?
 N2 C5 C6 110.1(4) . . ?
 H5A C5 H5B 108.1 . . ?
 C6 C5 H5A 109.6 . . ?
 C6 C5 H5B 109.6 . . ?
 N4 C6 C5 112.6(4) . . ?
 O2 C6 N4 126.8(5) . . ?
 O2 C6 C5 120.5(4) . . ?
 N1 C7 H7A 107.9 . . ?
 N1 C7 H7B 107.9 . . ?
 N1 C7 C8 117.5(4) . . ?
 H7A C7 H7B 107.2 . . ?
 C8 C7 H7A 107.9 . . ?
 C8 C7 H7B 107.9 . . ?
 O3 C8 O4 123.1(5) . . ?
 O3 C8 C7 125.4(4) . . ?
 O4 C8 C7 111.5(4) . . ?
 N2 C9 H9A 109.4 . . ?
 N2 C9 H9B 109.4 . . ?
 N2 C9 C10 111.0(4) . . ?
 H9A C9 H9B 108.0 . . ?
 C10 C9 H9A 109.4 . . ?
 C10 C9 H9B 109.4 . . ?
 O5 C10 O6 127.4(5) . . ?
 O5 C10 C9 116.7(5) . . ?
 O6 C10 C9 115.9(5) . . ?
 C12 C11 N3 117.8(5) . . ?
 C12 C11 C16 119.3(5) . . ?
 C16 C11 N3 122.9(5) . . ?
 C11 C12 H12 119.6 . . ?
 C11 C12 C13 120.7(6) . . ?
 C13 C12 H12 119.6 . . ?
 C12 C13 H13 120.0 . . ?
 C14 C13 C12 120.0(7) . . ?
 C14 C13 H13 120.0 . . ?
 C13 C14 H14 120.4 . . ?
 C15 C14 C13 119.1(6) . . ?
 C15 C14 H14 120.4 . . ?
 C14 C15 H15 119.5 . . ?
 C16 C15 C14 121.0(6) . . ?
 C16 C15 H15 119.5 . . ?
 C11 C16 H16 120.1 . . ?
 C15 C16 C11 119.8(6) . . ?
 C15 C16 H16 120.1 . . ?
 C18 C17 N4 117.5(5) . . ?
 C18 C17 C22 119.2(5) . . ?
 C22 C17 N4 123.3(5) . . ?
 C17 C18 H18 119.8 . . ?
 C17 C18 C19 120.3(6) . . ?
 C19 C18 H18 119.8 . . ?
 C18 C19 H19 119.8 . . ?
 C20 C19 C18 120.4(6) . . ?
 C20 C19 H19 119.8 . . ?
 C19 C20 H20 120.6 . . ?
 C19 C20 C21 118.8(6) . . ?
 C21 C20 H20 120.6 . . ?
 C20 C21 H21 119.1 . . ?
 C20 C21 C22 121.8(6) . . ?
 C22 C21 H21 119.1 . . ?
 C17 C22 H22 120.3 . . ?
 C21 C22 C17 119.4(6) . . ?
 C21 C22 H22 120.3 . . ?
 H31A O31 H31B 109.5 . . ?
 H32A O32 H32B 109.5 . . ?

loop_
  _geom_torsion_atom_site_label_1
  _geom_torsion_atom_site_label_2
  _geom_torsion_atom_site_label_3
  _geom_torsion_atom_site_label_4
  _geom_torsion
  _geom_torsion_site_symmetry_1
  _geom_torsion_site_symmetry_2
  _geom_torsion_site_symmetry_3
  _geom_torsion_site_symmetry_4
  _geom_torsion_publ_flag
 N1 C3 C4 N2 -51.3(5) . . . . ?
 N1 C7 C8 O3 2.3(8) . . . . ?
 N1 C7 C8 O4 -178.6(4) . . . . ?
 N2 C5 C6 N4 -177.5(4) . . . . ?
 N2 C5 C6 O2 0.3(6) . . . . ?
 N2 C9 C10 O5 0.7(7) . . . . ?
 N2 C9 C10 O6 -177.0(4) . . . . ?
 N3 C1 C2 N1 146.7(5) . . . . ?
 N3 C11 C12 C13 175.3(5) . . . . ?
 N3 C11 C16 C15 -174.8(5) . . . . ?
 N4 C17 C18 C19 -179.6(5) . . . . ?
 N4 C17 C22 C21 178.1(5) . . . . ?
 O1 C1 C2 N1 -35.2(8) . . . . ?
 C1 N3 C11 C12 161.7(6) . . . . ?
 C1 N3 C11 C16 -20.5(8) . . . . ?
 C2 N1 C3 C4 150.3(4) . . . . ?
 C2 N1 C7 C8 62.1(6) . . . . ?
 C3 N1 C2 C1 -64.2(6) . . . . ?
 C3 N1 C7 C8 -70.5(6) . . . . ?
 C4 N2 C5 C6 153.5(4) . . . . ?
 C4 N2 C9 C10 -81.3(5) . . . . ?
 C5 N2 C4 C3 -76.0(5) . . . . ?
 C5 N2 C9 C10 151.0(4) . . . . ?
 C6 N4 C17 C18 -159.1(5) . . . . ?
 C6 N4 C17 C22 22.4(8) . . . . ?
 C7 N1 C2 C1 162.0(5) . . . . ?
 C7 N1 C3 C4 -76.9(5) . . . . ?
 C9 N2 C4 C3 157.3(4) . . . . ?
 C9 N2 C5 C6 -80.2(5) . . . . ?
 C11 N3 C1 O1 -3.0(10) . . . . ?
 C11 N3 C1 C2 175.0(5) . . . . ?
 C11 C12 C13 C14 1.4(10) . . . . ?
 C12 C11 C16 C15 2.9(8) . . . . ?
 C12 C13 C14 C15 -0.6(11) . . . . ?
 C13 C14 C15 C16 1.0(11) . . . . ?
 C14 C15 C16 C11 -2.2(10) . . . . ?
 C16 C11 C12 C13 -2.5(9) . . . . ?
 C17 N4 C6 O2 -8.1(9) . . . . ?
 C17 N4 C6 C5 169.5(4) . . . . ?
 C17 C18 C19 C20 1.2(9) . . . . ?
 C18 C17 C22 C21 -0.4(8) . . . . ?
 C18 C19 C20 C21 0.1(9) . . . . ?
 C19 C20 C21 C22 -1.5(9) . . . . ?
 C20 C21 C22 C17 1.7(9) . . . . ?
 C22 C17 C18 C19 -1.0(8) . . . . ?

_shelx_SHELXL_version_number      '2014/7'
_olex2_submission_special_instructions 'No special instructions were received'
