# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 2019

####################################################################### 
# 
# 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_mm7
_database_code_depnum_ccdc_archive 'CCDC 1902693'
loop_
_audit_author_name
_audit_author_address
'Krzysztof Brzezinski'
;University of Bialystok
Poland
;
_audit_update_record             
;
2019-03-12 deposited with the CCDC.	2019-06-27 downloaded from the CCDC.
;
_audit_creation_date             2019-03-11
_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6

#===================================================================
# CHEMICAL DATA

_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C24 H16 N4 O5 V, C6 H16 N'
_chemical_formula_sum            'C30 H32 N5 O5 V'
_chemical_formula_weight         593.54
_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 0.0181 0.0091 '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 0.0311 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'
V V 0.0687 2.1097 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

#====================================================================
# CRYSTAL DATA

_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                   9.1706(2)
_cell_length_b                   11.5525(2)
_cell_length_c                   15.4622(3)
_cell_angle_alpha                109.4506(16)
_cell_angle_beta                 93.1694(16)
_cell_angle_gamma                112.1972(18)
_cell_volume                     1399.04(5)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    38345
_cell_measurement_theta_min      4.3520
_cell_measurement_theta_max      76.3680

_exptl_absorpt_coefficient_mu    3.374
_exptl_absorpt_correction_T_min  0.41858
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.41r (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_oxdiff_exptl_absorpt_empirical_full_min 0.608
_oxdiff_exptl_absorpt_empirical_full_max 1.611
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_exptl_crystal_density_diffrn    1.409
_exptl_crystal_colour            black
_exptl_crystal_description       prism
_exptl_crystal_F_000             620
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.07

#========================================================================
# EXPERIMENTAL DATA

_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_detector_area_resol_mean 10.4052
_diffrn_reflns_av_R_equivalents  0.0490
_diffrn_reflns_av_unetI/netI     0.0176
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            58089
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.417
_diffrn_reflns_theta_min         3.098
_diffrn_ambient_temperature      100(2)

_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0404095000
_diffrn_orient_matrix_UB_12      0.0381730000
_diffrn_orient_matrix_UB_13      -0.0849521000
_diffrn_orient_matrix_UB_21      -0.0914109000
_diffrn_orient_matrix_UB_22      -0.1498695000
_diffrn_orient_matrix_UB_23      -0.0659588000
_diffrn_orient_matrix_UB_31      -0.1562380000
_diffrn_orient_matrix_UB_32      0.0196749000
_diffrn_orient_matrix_UB_33      -0.0099779000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -79.00 -16.00   1.00    1.00    --    0.00 151.00  59.00   63
  2  ω    -60.00   1.00   1.00    1.00    --    0.00 122.00-101.00   61
  3  ω   -143.00 -74.00   1.00    1.18    --  -59.00-122.00 177.00   69
  4  ω   -147.00 -56.00   1.00    1.18    --  -59.00-151.00  15.00   91
  5  ω    -94.00   1.00   1.00    1.18    --  -59.00 122.00-101.00   95
  6  ω     37.00 135.00   1.00    1.18    --   59.00-151.00  15.00   98
  7  ω     79.00 146.00   1.00    1.18    --   59.00 151.00  59.00   67
  8  ω     21.00 119.00   1.00    1.18    --   59.00-122.00 177.00   98
  9  ω     96.00 178.00   1.00    1.18    --  118.00 122.00-101.00   82
 10  ω     37.00 135.00   1.00    1.18    --  118.00-151.00  15.00   98
 11  ω     34.00 119.00   1.00    1.18    --  118.00-122.00 177.00   85
 12  ω     78.00 171.00   1.00    1.18    --  118.00 151.00  59.00   93
 13  ω    -37.00  84.00   1.00    1.00    --    0.00  57.00   0.00  121
 14  ω      1.00  47.00   1.00    1.00    --    0.00 -99.00-150.00   46
 15  ω   -143.00 -73.00   1.00    1.18    --  -59.00-125.00 -60.00   70
 16  ω   -143.00 -22.00   1.00    1.18    --  -59.00 -57.00-150.00  121
 17  ω   -143.00 -22.00   1.00    1.18    --  -59.00 -38.00 -60.00  121
 18  ω   -148.00 -79.00   1.00    1.18    --  -59.00 -99.00 -60.00   69
 19  ω     94.00 143.00   1.00    1.18    --   59.00 125.00 150.00   49
 20  ω     94.00 143.00   1.00    1.18    --   59.00 125.00 -60.00   49
 21  ω     32.00 116.00   1.00    1.18    --  118.00-111.00-150.00   84
 22  ω     82.00 178.00   1.00    1.18    --  118.00  50.00 -90.00   96
 23  ω     79.00 178.00   1.00    1.18    --  118.00  77.00-150.00   99
 24  ω     32.00 155.00   1.00    1.18    --  118.00 -64.00 150.00  123
 25  ω     32.00 116.00   1.00    1.18    --  118.00-111.00  60.00   84
 26  ω     81.00 178.00   1.00    1.18    --  118.00  64.00-120.00   97
 27  ω     81.00 178.00   1.00    1.18    --  118.00  38.00 -30.00   97
 28  ω     82.00 178.00   1.00    1.18    --  118.00  50.00 150.00   96
 29  ω     81.00 178.00   1.00    1.18    --  118.00  38.00 -60.00   97
 30  ω     32.00 116.00   1.00    1.18    --  118.00-111.00 -60.00   84
 31  ω     57.00 150.00   1.00    1.18    --  118.00 178.00  60.00   93
 32  ω     32.00 116.00   1.00    1.18    --  118.00-111.00-120.00   84
 33  ω     27.00 162.00   1.00    1.18    --  118.00 -92.00 -60.00  135
 34  ω    100.00 178.00   1.00    1.18    --  118.00 111.00-150.00   78
 35  ω     81.00 178.00   1.00    1.18    --  118.00  38.00-150.00   97
 36  ω     27.00 162.00   1.00    1.18    --  118.00 -92.00  30.00  135
 37  ω     26.00 157.00   1.00    1.18    --  118.00 -77.00 -30.00  131
 38  ω     57.00 150.00   1.00    1.18    --  118.00 178.00 -30.00   93
 39  ω     32.00 155.00   1.00    1.18    --  118.00 -64.00  30.00  123
 40  ω     34.00 155.00   1.00    1.18    --  118.00 -38.00 -90.00  121
 41  ω     81.00 178.00   1.00    1.18    --  118.00  38.00-180.00   97
 42  ω     32.00 116.00   1.00    1.18    --  118.00-111.00  90.00   84
 43  ω     82.00 178.00   1.00    1.18    --  118.00  50.00  60.00   96
 44  ω    100.00 178.00   1.00    1.18    --  118.00 111.00 120.00   78
 45  ω     32.00 155.00   1.00    1.18    --  118.00 -64.00  90.00  123
 46  ω     26.00 157.00   1.00    1.18    --  118.00 -77.00-150.00  131
 47  ω     27.00 162.00   1.00    1.18    --  118.00 -92.00  90.00  135
 48  ω     79.00 178.00   1.00    1.18    --  118.00  77.00-180.00   99
 49  ω      1.00  47.00   1.00    1.00    --    0.00 -99.00 -60.00   46
 50  ω      1.00  47.00   1.00    1.00    --    0.00 -99.00  30.00   46
 51  ω    -92.00  39.00   1.00    1.00    --    0.00 -77.00 -30.00  131
 52  ω      1.00  47.00   1.00    1.00    --    0.00 -99.00  60.00   46
 53  ω   -151.00 -20.00   1.00    1.18    --  -59.00 -77.00 120.00  131
 54  ω   -143.00 -22.00   1.00    1.18    --  -59.00 -57.00  90.00  121
 55  ω   -151.00 -20.00   1.00    1.18    --  -59.00 -77.00-150.00  131
 56  ω   -151.00 -20.00   1.00    1.18    --  -59.00 -77.00  60.00  131
 57  ω   -151.00 -20.00   1.00    1.18    --  -59.00 -77.00-180.00  131
 58  ω   -151.00 -20.00   1.00    1.18    --  -59.00 -77.00 -60.00  131
 59  ω   -151.00 -20.00   1.00    1.18    --  -59.00 -77.00 -30.00  131
 60  ω   -151.00 -20.00   1.00    1.18    --  -59.00 -77.00 150.00  131
 61  ω   -151.00 -20.00   1.00    1.18    --  -59.00 -77.00   0.00  131
 62  ω     94.00 143.00   1.00    1.18    --   59.00 125.00  30.00   49
 63  ω     19.00  46.00   1.00    1.18    --   59.00  81.00 -83.93   27
 64  ω     22.00 143.00   1.00    1.18    --   59.00  57.00 -90.00  121
 65  ω     81.00 178.00   1.00    1.18    --  118.00  64.00 -90.00   97
 66  ω     81.00 178.00   1.00    1.18    --  118.00  64.00-150.00   97
 67  ω     79.00 178.00   1.00    1.18    --  118.00  77.00  90.00   99
 68  ω     79.00 178.00   1.00    1.18    --  118.00  77.00 150.00   99
 69  ω     79.00 178.00   1.00    1.18    --  118.00  77.00 -60.00   99
 70  ω     79.00 178.00   1.00    1.18    --  118.00  77.00 -90.00   99
 71  ω     79.00 178.00   1.00    1.18    --  118.00  77.00 -30.00   99
 72  ω     81.00 178.00   1.00    1.18    --  118.00  64.00  30.00   97
 73  ω     81.00 178.00   1.00    1.18    --  118.00  64.00  60.00   97
 74  ω     79.00 178.00   1.00    1.18    --  118.00  77.00  60.00   99
 75  ω     81.00 178.00   1.00    1.18    --  118.00  64.00 120.00   97
 76  ω     81.00 178.00   1.00    1.18    --  118.00  64.00 -30.00   97
 77  ω     81.00 178.00   1.00    1.18    --  118.00  64.00   0.00   97
 78  ω     81.00 178.00   1.00    1.18    --  118.00  64.00 -60.00   97
 79  ω     81.00 178.00   1.00    1.18    --  118.00  64.00  90.00   97
 80  ω     81.00 178.00   1.00    1.18    --  118.00  64.00-180.00   97
 81  ω     79.00 178.00   1.00    1.18    --  118.00  77.00-120.00   99
 82  ω     80.00 178.00   1.00    1.18    --  118.00  66.00   4.62   98
 83  ω     80.00 178.00   1.00    1.18    --  118.00  71.00  31.11   98
 84  ω     79.00 178.00   1.00    1.18    --  118.00  77.00   0.00   99
 85  ω     79.00 178.00   1.00    1.18    --  118.00  77.00 120.00   99
 86  ω     81.00 178.00   1.00    1.18    --  118.00  60.00 -47.69   97
 87  ω     81.00 178.00   1.00    1.18    --  118.00  64.00 150.00   97
;
_diffrn_measurement_method       'ω scans'

_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5772
_reflns_number_total             5860
_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       'CrysAlis PRO (Agilent Technologies, 2011)'
_computing_data_reduction        'CrysAlis PRO (Agilent Technologies, 2011)'
_computing_structure_solution    'SHELXT-2016(Sheldrick, 2016)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2016)'
_computing_molecular_graphics    'OLEX2 (Dolomanov et al., 2009)'
_computing_publication_material  'SHELXL-2018/3 (Sheldrick, 2016)'

#========================================================================= 
# REFINEMENT

_refine_diff_density_max         0.707
_refine_diff_density_min         -0.580
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       0.0012(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     436
_refine_ls_number_reflns         5860
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0394
_refine_ls_R_factor_gt           0.0389
_refine_ls_restrained_S_all      1.092
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0720P)²+0.5265P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1122
_refine_ls_wR_factor_ref         0.1129
_refine_special_details          ?

_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   ?

#=========================================================================
# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

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
V1 V 0.75160(3) 0.09715(2) 0.35446(2) 0.02012(10) Uani 1 1 d . . . . .
O1 O 0.90168(13) 0.14793(11) 0.27236(8) 0.0228(2) Uani 1 1 d . . . . .
O2 O 0.67737(16) 0.13835(12) 0.46848(9) 0.0305(3) Uani 1 1 d . . . . .
O3 O 0.58349(17) 0.00578(16) 0.27942(10) 0.0491(4) Uani 1 1 d . . . . .
O4 O 0.83081(18) 0.00103(14) 0.37478(11) 0.0433(4) Uani 1 1 d . . . . .
O5 O 1.08478(15) 0.53826(12) 0.26359(9) 0.0282(3) Uani 1 1 d . . . . .
H5 H 1.031(3) 0.507(3) 0.2987(18) 0.042 Uiso 1 1 d R . . . .
N1 N 0.92312(15) 0.36480(13) 0.33405(9) 0.0215(3) Uani 1 1 d . . . . .
N2 N 0.82409(15) 0.30987(12) 0.38840(9) 0.0197(2) Uani 1 1 d . . . . .
N3 N 0.50581(17) 0.53523(15) 0.69044(10) 0.0281(3) Uani 1 1 d . . . . .
N4 N 0.42395(18) 0.50809(15) 0.74948(10) 0.0296(3) Uani 1 1 d . . . . .
N5 N 0.93021(17) 1.07116(14) 0.68079(10) 0.0265(3) Uani 1 1 d . . . . .
H5B H 1.001(3) 1.045(2) 0.6580(15) 0.032 Uiso 1 1 d R . . . .
C1 C 0.95456(17) 0.27054(15) 0.27439(10) 0.0200(3) Uani 1 1 d . . . . .
C2 C 1.05348(17) 0.30482(15) 0.20713(10) 0.0205(3) Uani 1 1 d . . . . .
C3 C 1.08534(18) 0.20536(15) 0.14367(10) 0.0215(3) Uani 1 1 d . . . . .
H3 H 1.046727 0.118243 0.146538 0.026 Uiso 1 1 calc R . . . .
C4 C 1.17359(18) 0.22904(16) 0.07458(11) 0.0224(3) Uani 1 1 d . . . . .
C5 C 1.20570(19) 0.12644(17) 0.00874(11) 0.0264(3) Uani 1 1 d . . . . .
H5A H 1.168090 0.039053 0.011117 0.032 Uiso 1 1 calc R . . . .
C6 C 1.2902(2) 0.15214(19) -0.05805(12) 0.0309(4) Uani 1 1 d . . . . .
H6 H 1.310912 0.082862 -0.101769 0.037 Uiso 1 1 calc R . . . .
C7 C 1.3464(2) 0.2818(2) -0.06176(13) 0.0343(4) Uani 1 1 d . . . . .
H7 H 1.404660 0.299259 -0.108317 0.041 Uiso 1 1 calc R . . . .
C8 C 1.3178(2) 0.38289(19) 0.00107(13) 0.0327(4) Uani 1 1 d . . . . .
H8 H 1.356815 0.469656 -0.002396 0.039 Uiso 1 1 calc R . . . .
C9 C 1.23055(19) 0.35962(17) 0.07128(11) 0.0251(3) Uani 1 1 d . . . . .
C10 C 1.1990(2) 0.46164(17) 0.13681(12) 0.0269(3) Uani 1 1 d . . . . .
H10 H 1.238316 0.549338 0.134887 0.032 Uiso 1 1 calc R . . . .
C11 C 1.11244(18) 0.43625(16) 0.20333(11) 0.0231(3) Uani 1 1 d . . . . .
C12 C 0.77911(18) 0.39270(15) 0.44761(11) 0.0218(3) Uani 1 1 d . . . . .
H12 H 0.813194 0.481601 0.448287 0.026 Uiso 1 1 calc R . . . .
C13 C 0.68135(18) 0.35841(15) 0.51195(11) 0.0213(3) Uani 1 1 d . . . . .
C14 C 0.63407(19) 0.45467(15) 0.57040(11) 0.0238(3) Uani 1 1 d . . . . .
H14 H 0.665065 0.539813 0.564915 0.029 Uiso 1 1 calc R . . . .
C15 C 0.54361(19) 0.42792(16) 0.63554(11) 0.0251(3) Uani 1 1 d . . . . .
C16 C 0.3926(2) 0.61812(18) 0.80750(12) 0.0292(3) Uani 1 1 d . . . . .
C17 C 0.4562(2) 0.74822(19) 0.80641(12) 0.0324(4) Uani 1 1 d . . . . .
H17 H 0.522960 0.768217 0.763760 0.039 Uiso 1 1 calc R . . . .
C18 C 0.4209(2) 0.8478(2) 0.86812(13) 0.0370(4) Uani 1 1 d . . . . .
H18 H 0.462996 0.936291 0.867565 0.044 Uiso 1 1 calc R . . . .
C19 C 0.3246(2) 0.8184(2) 0.93041(13) 0.0384(4) Uani 1 1 d . . . . .
H19 H 0.302704 0.887471 0.973419 0.046 Uiso 1 1 calc R . . . .
C20 C 0.2596(2) 0.6890(2) 0.93078(13) 0.0396(4) Uani 1 1 d . . . . .
H20 H 0.192337 0.669234 0.973259 0.048 Uiso 1 1 calc R . . . .
C21 C 0.2933(2) 0.5884(2) 0.86881(12) 0.0347(4) Uani 1 1 d . . . . .
H21 H 0.248533 0.499357 0.868423 0.042 Uiso 1 1 calc R . . . .
C22 C 0.4993(2) 0.30166(17) 0.64425(11) 0.0270(3) Uani 1 1 d . . . . .
H22 H 0.438254 0.282722 0.689459 0.032 Uiso 1 1 calc R . . . .
C23 C 0.5440(2) 0.20623(16) 0.58769(12) 0.0269(3) Uani 1 1 d . . . . .
H23 H 0.513175 0.121713 0.594135 0.032 Uiso 1 1 calc R . . . .
C24 C 0.63505(19) 0.23193(16) 0.52017(11) 0.0228(3) Uani 1 1 d . . . . .
C25A C 0.7799(5) 0.9687(4) 0.6110(3) 0.0398(10) Uani 0.504(4) 1 d . . P A 1
H25A H 0.791697 0.971863 0.548499 0.048 Uiso 0.504(4) 1 calc R . P A 1
H25B H 0.689116 0.991764 0.628240 0.048 Uiso 0.504(4) 1 calc R . P A 1
C25B C 0.7814(4) 0.9500(3) 0.6842(3) 0.0275(8) Uani 0.496(4) 1 d . . P A 2
H25C H 0.803172 0.934301 0.741741 0.033 Uiso 0.496(4) 1 calc R . P A 2
H25D H 0.686229 0.971077 0.685464 0.033 Uiso 0.496(4) 1 calc R . P A 2
C26A C 0.7408(15) 0.8256(12) 0.6055(9) 0.067(4) Uani 0.504(4) 1 d . . P A 1
H26A H 0.641338 0.762017 0.558836 0.101 Uiso 0.504(4) 1 calc R . P A 1
H26B H 0.829324 0.801494 0.587138 0.101 Uiso 0.504(4) 1 calc R . P A 1
H26C H 0.726740 0.821395 0.666882 0.101 Uiso 0.504(4) 1 calc R . P A 1
C26B C 0.7491(11) 0.8280(9) 0.6008(5) 0.025(2) Uani 0.496(4) 1 d . . P A 2
H26D H 0.655752 0.751631 0.602607 0.037 Uiso 0.496(4) 1 calc R . P A 2
H26E H 0.726728 0.843958 0.544144 0.037 Uiso 0.496(4) 1 calc R . P A 2
H26F H 0.843353 0.807282 0.600268 0.037 Uiso 0.496(4) 1 calc R . P A 2
C27A C 0.9381(7) 1.0880(6) 0.7749(3) 0.0440(11) Uani 0.504(4) 1 d . . P A 1
H27A H 1.048876 1.152185 0.810324 0.053 Uiso 0.504(4) 1 calc R . P A 1
H27B H 0.917332 0.999957 0.779677 0.053 Uiso 0.504(4) 1 calc R . P A 1
C27B C 1.0190(5) 1.1617(4) 0.7825(2) 0.0251(7) Uani 0.496(4) 1 d . . P A 2
H27C H 1.045351 1.106428 0.812326 0.030 Uiso 0.496(4) 1 calc R . P A 2
H27D H 1.121836 1.232845 0.782300 0.030 Uiso 0.496(4) 1 calc R . P A 2
C28A C 0.8205(9) 1.1397(8) 0.8213(4) 0.0704(18) Uani 0.504(4) 1 d . . P A 1
H28A H 0.710807 1.079850 0.784814 0.106 Uiso 0.504(4) 1 calc GR . P A 1
H28B H 0.847884 1.231468 0.823706 0.106 Uiso 0.504(4) 1 calc GR . P A 1
H28C H 0.827298 1.140949 0.885074 0.106 Uiso 0.504(4) 1 calc GR . P A 1
C28B C 0.9253(5) 1.2286(5) 0.8408(3) 0.0357(9) Uani 0.496(4) 1 d . . P A 2
H28D H 0.904421 1.288166 0.814119 0.053 Uiso 0.496(4) 1 calc GR . P A 2
H28E H 0.987845 1.282057 0.905191 0.053 Uiso 0.496(4) 1 calc GR . P A 2
H28F H 0.822837 1.159173 0.841115 0.053 Uiso 0.496(4) 1 calc GR . P A 2
C29A C 0.9756(7) 1.2105(5) 0.6696(4) 0.0504(14) Uani 0.496(4) 1 d . . P A 1
H29A H 0.875702 1.224540 0.666520 0.060 Uiso 0.496(4) 1 calc R . P A 1
H29B H 1.049771 1.281542 0.728637 0.060 Uiso 0.496(4) 1 calc R . P A 1
C29B C 0.8896(4) 1.1385(4) 0.6256(2) 0.0216(7) Uani 0.504(4) 1 d . . P A 2
H29C H 0.832295 1.191704 0.658764 0.026 Uiso 0.504(4) 1 calc R . P A 2
H29D H 0.819881 1.071630 0.564093 0.026 Uiso 0.504(4) 1 calc R . P A 2
C30A C 1.0358(8) 1.2343(5) 0.6060(3) 0.0262(11) Uani 0.504(4) 1 d . . P A 1
H30A H 0.956671 1.179038 0.546775 0.039 Uiso 0.504(4) 1 calc GR . P A 1
H30B H 1.129479 1.212847 0.602374 0.039 Uiso 0.504(4) 1 calc GR . P A 1
H30C H 1.069818 1.330378 0.617593 0.039 Uiso 0.504(4) 1 calc GR . P A 1
C30B C 1.0682(13) 1.2422(12) 0.6112(10) 0.105(5) Uani 0.496(4) 1 d . . P A 2
H30D H 1.047953 1.285365 0.569947 0.157 Uiso 0.496(4) 1 calc GR . P A 2
H30E H 1.127315 1.188911 0.583164 0.157 Uiso 0.496(4) 1 calc GR . P A 2
H30F H 1.132255 1.311866 0.672341 0.157 Uiso 0.496(4) 1 calc GR . P A 2


#=========================================================================
# MOLECULAR GEOMETRY

_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
V1 O1 1.9822(11) . ?
V1 O2 1.9017(12) . ?
V1 O3 1.6106(14) . ?
V1 O4 1.6358(13) . ?
V1 N2 2.1505(12) . ?
O1 C1 1.3008(18) . ?
O2 C24 1.3169(18) . ?
O5 H5 0.83(3) . ?
O5 C11 1.3573(19) . ?
N1 N2 1.3921(17) . ?
N1 C1 1.3105(19) . ?
N2 C12 1.2964(19) . ?
N3 N4 1.259(2) . ?
N3 C15 1.426(2) . ?
N4 C16 1.431(2) . ?
N5 H5B 0.86(2) . ?
N5 C25A 1.489(4) . ?
N5 C25B 1.561(3) . ?
N5 C27A 1.397(5) . ?
N5 C27B 1.533(4) . ?
N5 C29A 1.576(4) . ?
N5 C29B 1.449(3) . ?
C1 C2 1.473(2) . ?
C2 C3 1.379(2) . ?
C2 C11 1.430(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.412(2) . ?
C4 C5 1.422(2) . ?
C4 C9 1.418(2) . ?
C5 H5A 0.9500 . ?
C5 C6 1.369(2) . ?
C6 H6 0.9500 . ?
C6 C7 1.410(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.371(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.421(2) . ?
C9 C10 1.412(2) . ?
C10 H10 0.9500 . ?
C10 C11 1.375(2) . ?
C12 H12 0.9500 . ?
C12 C13 1.429(2) . ?
C13 C14 1.407(2) . ?
C13 C24 1.412(2) . ?
C14 H14 0.9500 . ?
C14 C15 1.380(2) . ?
C15 C22 1.414(2) . ?
C16 C17 1.398(3) . ?
C16 C21 1.386(3) . ?
C17 H17 0.9500 . ?
C17 C18 1.386(2) . ?
C18 H18 0.9500 . ?
C18 C19 1.381(3) . ?
C19 H19 0.9500 . ?
C19 C20 1.387(3) . ?
C20 H20 0.9500 . ?
C20 C21 1.388(3) . ?
C21 H21 0.9500 . ?
C22 H22 0.9500 . ?
C22 C23 1.374(2) . ?
C23 H23 0.9500 . ?
C23 C24 1.411(2) . ?
C25A H25A 0.9900 . ?
C25A H25B 0.9900 . ?
C25A C26A 1.524(12) . ?
C25B H25C 0.9900 . ?
C25B H25D 0.9900 . ?
C25B C26B 1.473(9) . ?
C26A H26A 0.9800 . ?
C26A H26B 0.9800 . ?
C26A H26C 0.9800 . ?
C26B H26D 0.9800 . ?
C26B H26E 0.9800 . ?
C26B H26F 0.9800 . ?
C27A H27A 0.9900 . ?
C27A H27B 0.9900 . ?
C27A C28A 1.523(6) . ?
C27B H27C 0.9900 . ?
C27B H27D 0.9900 . ?
C27B C28B 1.508(5) . ?
C28A H28A 0.9800 . ?
C28A H28B 0.9800 . ?
C28A H28C 0.9800 . ?
C28B H28D 0.9800 . ?
C28B H28E 0.9800 . ?
C28B H28F 0.9800 . ?
C29A H29A 0.9900 . ?
C29A H29B 0.9900 . ?
C29A C30A 1.213(8) . ?
C29B H29C 0.9900 . ?
C29B H29D 0.9900 . ?
C29B C30B 1.704(11) . ?
C30A H30A 0.9800 . ?
C30A H30B 0.9800 . ?
C30A H30C 0.9800 . ?
C30B H30D 0.9800 . ?
C30B H30E 0.9800 . ?
C30B H30F 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 V1 N2 73.53(4) . . ?
O2 V1 O1 151.65(5) . . ?
O2 V1 N2 81.79(5) . . ?
O3 V1 O1 101.14(6) . . ?
O3 V1 O2 100.97(7) . . ?
O3 V1 O4 110.31(9) . . ?
O3 V1 N2 112.22(7) . . ?
O4 V1 O1 92.43(5) . . ?
O4 V1 O2 96.32(6) . . ?
O4 V1 N2 136.99(7) . . ?
C1 O1 V1 118.72(9) . . ?
C24 O2 V1 137.36(10) . . ?
C11 O5 H5 106.4(17) . . ?
C1 N1 N2 109.22(12) . . ?
N1 N2 V1 115.76(9) . . ?
C12 N2 V1 129.21(10) . . ?
C12 N2 N1 114.81(12) . . ?
N4 N3 C15 113.70(14) . . ?
N3 N4 C16 113.63(15) . . ?
C25A N5 H5B 101.6(15) . . ?
C25A N5 C29A 108.6(3) . . ?
C25B N5 H5B 110.8(15) . . ?
C27A N5 H5B 111.7(14) . . ?
C27A N5 C25A 119.0(3) . . ?
C27A N5 C29A 110.9(3) . . ?
C27B N5 H5B 101.6(15) . . ?
C27B N5 C25B 106.8(2) . . ?
C29A N5 H5B 103.8(15) . . ?
C29B N5 H5B 108.0(14) . . ?
C29B N5 C25B 113.3(2) . . ?
C29B N5 C27B 115.7(2) . . ?
O1 C1 N1 122.49(13) . . ?
O1 C1 C2 118.80(13) . . ?
N1 C1 C2 118.71(13) . . ?
C3 C2 C1 118.78(13) . . ?
C3 C2 C11 119.06(13) . . ?
C11 C2 C1 122.12(13) . . ?
C2 C3 H3 119.0 . . ?
C2 C3 C4 122.04(14) . . ?
C4 C3 H3 119.0 . . ?
C3 C4 C5 122.13(14) . . ?
C3 C4 C9 118.30(14) . . ?
C9 C4 C5 119.57(14) . . ?
C4 C5 H5A 119.6 . . ?
C6 C5 C4 120.75(16) . . ?
C6 C5 H5A 119.6 . . ?
C5 C6 H6 120.1 . . ?
C5 C6 C7 119.80(16) . . ?
C7 C6 H6 120.1 . . ?
C6 C7 H7 119.6 . . ?
C8 C7 C6 120.74(16) . . ?
C8 C7 H7 119.6 . . ?
C7 C8 H8 119.6 . . ?
C7 C8 C9 120.89(16) . . ?
C9 C8 H8 119.6 . . ?
C4 C9 C8 118.25(15) . . ?
C10 C9 C4 119.58(14) . . ?
C10 C9 C8 122.17(15) . . ?
C9 C10 H10 119.4 . . ?
C11 C10 C9 121.14(14) . . ?
C11 C10 H10 119.4 . . ?
O5 C11 C2 121.90(14) . . ?
O5 C11 C10 118.22(14) . . ?
C10 C11 C2 119.88(14) . . ?
N2 C12 H12 118.0 . . ?
N2 C12 C13 123.99(13) . . ?
C13 C12 H12 118.0 . . ?
C14 C13 C12 119.12(13) . . ?
C14 C13 C24 119.23(14) . . ?
C24 C13 C12 121.63(13) . . ?
C13 C14 H14 119.3 . . ?
C15 C14 C13 121.34(14) . . ?
C15 C14 H14 119.3 . . ?
C14 C15 N3 115.18(14) . . ?
C14 C15 C22 119.16(14) . . ?
C22 C15 N3 125.65(14) . . ?
C17 C16 N4 124.71(16) . . ?
C21 C16 N4 114.94(16) . . ?
C21 C16 C17 120.34(16) . . ?
C16 C17 H17 120.3 . . ?
C18 C17 C16 119.41(18) . . ?
C18 C17 H17 120.3 . . ?
C17 C18 H18 120.0 . . ?
C19 C18 C17 120.04(19) . . ?
C19 C18 H18 120.0 . . ?
C18 C19 H19 119.7 . . ?
C18 C19 C20 120.66(17) . . ?
C20 C19 H19 119.7 . . ?
C19 C20 H20 120.1 . . ?
C19 C20 C21 119.71(18) . . ?
C21 C20 H20 120.1 . . ?
C16 C21 C20 119.82(19) . . ?
C16 C21 H21 120.1 . . ?
C20 C21 H21 120.1 . . ?
C15 C22 H22 119.8 . . ?
C23 C22 C15 120.37(14) . . ?
C23 C22 H22 119.8 . . ?
C22 C23 H23 119.5 . . ?
C22 C23 C24 120.95(15) . . ?
C24 C23 H23 119.5 . . ?
O2 C24 C13 122.16(14) . . ?
O2 C24 C23 118.89(14) . . ?
C23 C24 C13 118.93(14) . . ?
N5 C25A H25A 109.1 . . ?
N5 C25A H25B 109.1 . . ?
N5 C25A C26A 112.5(5) . . ?
H25A C25A H25B 107.8 . . ?
C26A C25A H25A 109.1 . . ?
C26A C25A H25B 109.1 . . ?
N5 C25B H25C 109.9 . . ?
N5 C25B H25D 109.9 . . ?
H25C C25B H25D 108.3 . . ?
C26B C25B N5 109.1(4) . . ?
C26B C25B H25C 109.9 . . ?
C26B C25B H25D 109.9 . . ?
C25A C26A H26A 109.5 . . ?
C25A C26A H26B 109.5 . . ?
C25A C26A H26C 109.5 . . ?
H26A C26A H26B 109.5 . . ?
H26A C26A H26C 109.5 . . ?
H26B C26A H26C 109.5 . . ?
C25B C26B H26D 109.5 . . ?
C25B C26B H26E 109.5 . . ?
C25B C26B H26F 109.5 . . ?
H26D C26B H26E 109.5 . . ?
H26D C26B H26F 109.5 . . ?
H26E C26B H26F 109.5 . . ?
N5 C27A H27A 108.6 . . ?
N5 C27A H27B 108.6 . . ?
N5 C27A C28A 114.8(4) . . ?
H27A C27A H27B 107.6 . . ?
C28A C27A H27A 108.6 . . ?
C28A C27A H27B 108.6 . . ?
N5 C27B H27C 108.7 . . ?
N5 C27B H27D 108.7 . . ?
H27C C27B H27D 107.6 . . ?
C28B C27B N5 114.1(3) . . ?
C28B C27B H27C 108.7 . . ?
C28B C27B H27D 108.7 . . ?
C27A C28A H28A 109.5 . . ?
C27A C28A H28B 109.5 . . ?
C27A C28A H28C 109.5 . . ?
H28A C28A H28B 109.5 . . ?
H28A C28A H28C 109.5 . . ?
H28B C28A H28C 109.5 . . ?
C27B C28B H28D 109.5 . . ?
C27B C28B H28E 109.5 . . ?
C27B C28B H28F 109.5 . . ?
H28D C28B H28E 109.5 . . ?
H28D C28B H28F 109.5 . . ?
H28E C28B H28F 109.5 . . ?
N5 C29A H29A 106.6 . . ?
N5 C29A H29B 106.6 . . ?
H29A C29A H29B 106.6 . . ?
C30A C29A N5 122.8(4) . . ?
C30A C29A H29A 106.6 . . ?
C30A C29A H29B 106.6 . . ?
N5 C29B H29C 110.6 . . ?
N5 C29B H29D 110.6 . . ?
N5 C29B C30B 105.7(4) . . ?
H29C C29B H29D 108.7 . . ?
C30B C29B H29C 110.6 . . ?
C30B C29B H29D 110.6 . . ?
C29A C30A H30A 109.5 . . ?
C29A C30A H30B 109.5 . . ?
C29A C30A H30C 109.5 . . ?
H30A C30A H30B 109.5 . . ?
H30A C30A H30C 109.5 . . ?
H30B C30A H30C 109.5 . . ?
C29B C30B H30D 109.5 . . ?
C29B C30B H30E 109.5 . . ?
C29B C30B H30F 109.5 . . ?
H30D C30B H30E 109.5 . . ?
H30D C30B H30F 109.5 . . ?
H30E C30B H30F 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O5 H5 N1 0.83(3) 1.84(3) 2.6054(17) 151(2) .
N5 H5B O4 0.86(2) 1.86(2) 2.7108(18) 172(2) 2_766

#=========================================================================
# Final .res file from SHELXL 

_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_mm-3
_database_code_depnum_ccdc_archive 'CCDC 1903091'
loop_
_audit_author_name
_audit_author_address
'Aurelien Crochet'
;University of Fribourg
Switzerland
;
_audit_update_record             
;
2019-03-13 deposited with the CCDC.	2019-06-27 downloaded from the CCDC.
;
_audit_creation_date             2019-03-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H14 N4 O5 V, C6 H16 N'
_chemical_formula_sum            'C26 H30 N5 O5 V'
_chemical_formula_weight         543.49
_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'
V V 0.3005 0.5294 '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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   6.8790(3)
_cell_length_b                   8.5804(3)
_cell_length_c                   22.3944(11)
_cell_angle_alpha                90
_cell_angle_beta                 91.071(4)
_cell_angle_gamma                90
_cell_volume                     1321.59(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    9616
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      25.57
_cell_measurement_theta_min      1.81
_shelx_estimated_absorpt_T_max   0.971
_shelx_estimated_absorpt_T_min   0.899
_exptl_absorpt_coefficient_mu    0.420
_exptl_absorpt_correction_T_max  0.9071
_exptl_absorpt_correction_T_min  0.7975
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   
;
STOE X-Red32, absorption correction by Gaussian integration, analogous to
P. Coppens, "The Evaluation of Absorption and Extinction in Single-Crystal
Structure Analysis", published in
F. R. Ahmed (Editor), "Crystallographic Computing",
Munksgaard, Copenhagen (1970), 255 - 270
Afterwards scaling of reflection intensities was performed within STOE LANA.
J. Koziskova, F. Hahn, J. Richter, J. Kozisek, "Comparison of different
absorption corrections on the model structure of tetrakis(μ₂-acetato)-
diaqua-di-copper(II)", Acta Chimica Slovaca, vol. 9, no. 2, 2016, pp. 136 - 140.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'orangish brown'
_exptl_crystal_colour_modifier   orangish
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.366
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             568
_exptl_crystal_recrystallization_method 
'The material was recrystallised from ethanol by slow evaporation'
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.137
_exptl_crystal_size_min          0.07
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0744
_diffrn_reflns_av_unetI/netI     0.0664
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.989
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            16895
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        25.181
_diffrn_reflns_theta_max         25.181
_diffrn_reflns_theta_min         1.819
_diffrn_ambient_temperature      200(2)
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.989
_diffrn_measurement_device_type  'STOE IPDS2'
_diffrn_measurement_method       'rotation method'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              'Stoe IPDS2'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.855
_reflns_Friedel_fraction_full    0.979
_reflns_Friedel_fraction_max     0.979
_reflns_number_gt                3448
_reflns_number_total             4671
_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       'X-Area (Stoe & Cie, 2009)'
_computing_data_collection       'X-Area (Stoe & Cie, 2009)'
_computing_data_reduction        'X-RED32(Stoe & Cie, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         1.064
_refine_diff_density_min         -0.316
_refine_diff_density_rms         0.075
_refine_ls_abs_structure_details 
;
 Flack x determined using 1217 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.019(17)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     340
_refine_ls_number_reflns         4671
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0880
_refine_ls_R_factor_gt           0.0643
_refine_ls_restrained_S_all      1.003
_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)+(0.0992P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1478
_refine_ls_wR_factor_ref         0.1607
_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 C(H,H,H) groups, All O(H) groups
2. Restrained distances
 H5A-O5
 0.95 with sigma of 0.02
 N5-H5B
 0.9 with sigma of 0.02
3.a Ternary CH refined with riding coordinates and stretchable bonds:
 N5(H5B)
3.b Secondary CH2 refined with riding coordinates:
 C21(H21A,H21B), C23(H23A,H23B), C25(H25A,H25B)
3.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C8(H8), C10(H10), C13(H13), C14(H14),
 C15(H15), C16(H16), C17(H17), C18(H18), C19(H19)
3.d Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C24(H24A,H24B,H24C), C26(H26A,H26B,H26C)
3.e Idealised tetrahedral OH refined as rotating group with stretchable bonds:
 O5(H5A)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.3350(11) 0.7412(10) 0.1266(3) 0.0438(17) Uani 1 1 d . . . . .
C2 C 0.3067(11) 0.8246(10) 0.0696(3) 0.0432(17) Uani 1 1 d . . . . .
C3 C 0.4668(12) 0.8629(11) 0.0351(4) 0.053(2) Uani 1 1 d . . . . .
H3 H 0.593292 0.833313 0.048541 0.064 Uiso 1 1 calc R . . . .
C4 C 0.4456(14) 0.9419(12) -0.0177(4) 0.063(2) Uani 1 1 d . . . . .
H4 H 0.556132 0.968046 -0.040454 0.076 Uiso 1 1 calc R . . . .
C5 C 0.2619(14) 0.9832(11) -0.0374(4) 0.061(2) Uani 1 1 d . . . . .
H5 H 0.247055 1.035591 -0.074574 0.073 Uiso 1 1 calc R . . . .
C6 C 0.1028(14) 0.9514(11) -0.0055(4) 0.056(2) Uani 1 1 d . . . . .
H6 H -0.021461 0.984914 -0.019583 0.067 Uiso 1 1 calc R . . . .
C7 C 0.1203(12) 0.8680(10) 0.0490(4) 0.0495(19) Uani 1 1 d . . . . .
C8 C 0.1096(11) 0.6204(8) 0.2511(3) 0.0416(18) Uani 1 1 d . . . . .
H8 H -0.014973 0.663805 0.242706 0.050 Uiso 1 1 calc R . . . .
C9 C 0.1386(11) 0.5372(9) 0.3055(3) 0.0466(19) Uani 1 1 d . . . . .
C10 C -0.0117(13) 0.5355(10) 0.3466(3) 0.0498(19) Uani 1 1 d . . . . .
H10 H -0.127684 0.592114 0.338156 0.060 Uiso 1 1 calc R . . . .
C11 C 0.0057(12) 0.4527(11) 0.3993(4) 0.053(2) Uani 1 1 d . . . . .
C12 C -0.2977(13) 0.4251(12) 0.5242(4) 0.060(2) Uani 1 1 d . . . . .
C13 C -0.4582(14) 0.5146(13) 0.5116(4) 0.066(3) Uani 1 1 d . . . . .
H13 H -0.464757 0.573794 0.475758 0.079 Uiso 1 1 calc R . . . .
C14 C -0.6114(15) 0.5191(15) 0.5511(4) 0.075(3) Uani 1 1 d . . . . .
H14 H -0.721074 0.583713 0.543292 0.090 Uiso 1 1 calc R . . . .
C15 C -0.6015(17) 0.4284(14) 0.6019(4) 0.075(3) Uani 1 1 d . . . . .
H15 H -0.709448 0.425380 0.627699 0.090 Uiso 1 1 calc R . . . .
C16 C -0.440(2) 0.3427(15) 0.6157(5) 0.085(3) Uani 1 1 d . . . . .
H16 H -0.434420 0.282806 0.651379 0.102 Uiso 1 1 calc R . . . .
C17 C -0.284(2) 0.3430(15) 0.5782(5) 0.081(3) Uani 1 1 d . . . . .
H17 H -0.168826 0.288006 0.588660 0.097 Uiso 1 1 calc R . . . .
C18 C 0.1742(16) 0.3716(13) 0.4107(4) 0.066(3) Uani 1 1 d . . . . .
H18 H 0.186341 0.314347 0.446898 0.080 Uiso 1 1 calc R . . . .
C19 C 0.3257(14) 0.3702(11) 0.3717(4) 0.059(2) Uani 1 1 d . . . . .
H19 H 0.439423 0.311338 0.380799 0.070 Uiso 1 1 calc R . . . .
C20 C 0.3125(11) 0.4565(10) 0.3181(3) 0.0463(18) Uani 1 1 d . . . . .
N1 N -0.1319(13) 0.4080(10) 0.4876(4) 0.065(2) Uani 1 1 d . . . . .
N2 N -0.1581(11) 0.4710(10) 0.4387(3) 0.0582(18) Uani 1 1 d . . . . .
N3 N 0.2447(8) 0.6393(7) 0.2129(3) 0.0401(14) Uani 1 1 d . . . . .
N4 N 0.1824(9) 0.7203(8) 0.1608(3) 0.0454(15) Uani 1 1 d . . . . .
O1 O 0.5050(7) 0.6899(7) 0.1412(2) 0.0477(13) Uani 1 1 d . . . . .
O2 O 0.4572(8) 0.4511(6) 0.2799(2) 0.0502(13) Uani 1 1 d . . . . .
O3 O 0.6532(8) 0.7259(6) 0.2564(2) 0.0461(12) Uani 1 1 d . . . . .
O4 O 0.7112(8) 0.4694(6) 0.1942(2) 0.0517(14) Uani 1 1 d . . . . .
O5 O -0.0439(8) 0.8336(8) 0.0779(3) 0.0552(14) Uani 1 1 d D . . . .
H5A H -0.013(2) 0.772(11) 0.112(3) 0.083 Uiso 1 1 calc DGR . . . .
V1 V 0.54676(16) 0.58943(14) 0.21950(5) 0.0394(3) Uani 1 1 d . . . . .
C21 C 0.7032(14) 0.0642(12) 0.1824(5) 0.068(3) Uani 1 1 d . . . . .
H21A H 0.657355 0.074815 0.140418 0.081 Uiso 1 1 calc R . . . .
H21B H 0.758027 -0.041791 0.187333 0.081 Uiso 1 1 calc R . . . .
C22 C 0.5378(14) 0.0811(19) 0.2216(6) 0.092(3) Uani 1 1 d . . . . .
H22A H 0.570628 0.037183 0.260874 0.138 Uiso 1 1 calc GR . . . .
H22B H 0.425561 0.025540 0.204347 0.138 Uiso 1 1 calc GR . . . .
H22C H 0.505922 0.191770 0.225810 0.138 Uiso 1 1 calc GR . . . .
C23 C 0.9317(19) 0.1742(13) 0.2557(7) 0.092(4) Uani 1 1 d . . . . .
H23A H 0.823593 0.201062 0.282393 0.110 Uiso 1 1 calc R . . . .
H23B H 1.033077 0.255225 0.261011 0.110 Uiso 1 1 calc R . . . .
C24 C 1.017(2) 0.0179(16) 0.2758(8) 0.104(5) Uani 1 1 d . . . . .
H24A H 0.922342 -0.065097 0.267626 0.156 Uiso 1 1 calc GR . . . .
H24B H 1.047101 0.021602 0.318692 0.156 Uiso 1 1 calc GR . . . .
H24C H 1.136212 -0.002917 0.253863 0.156 Uiso 1 1 calc GR . . . .
C25 C 1.0062(17) 0.1642(15) 0.1436(6) 0.085(3) Uani 1 1 d . . . . .
H25A H 1.084339 0.068714 0.150374 0.102 Uiso 1 1 calc R . . . .
H25B H 0.934205 0.151880 0.105237 0.102 Uiso 1 1 calc R . . . .
C26 C 1.137(2) 0.2972(15) 0.1394(6) 0.093(4) Uani 1 1 d . . . . .
H26A H 1.062062 0.389701 0.127320 0.139 Uiso 1 1 calc GR . . . .
H26B H 1.235628 0.275512 0.109581 0.139 Uiso 1 1 calc GR . . . .
H26C H 1.199817 0.315853 0.178273 0.139 Uiso 1 1 calc GR . . . .
N5 N 0.8594(11) 0.1805(8) 0.1942(4) 0.065(2) Uani 1 1 d D . . . .
H5B H 0.804(2) 0.275(3) 0.1896(4) 0.078 Uiso 1 1 calc DGR . . . .


_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 C2 1.474(11) . ?
C1 N4 1.324(9) . ?
C1 O1 1.286(9) . ?
C2 C3 1.397(11) . ?
C2 C7 1.404(11) . ?
C3 H3 0.9500 . ?
C3 C4 1.368(12) . ?
C4 H4 0.9500 . ?
C4 C5 1.377(13) . ?
C5 H5 0.9500 . ?
C5 C6 1.346(13) . ?
C6 H6 0.9500 . ?
C6 C7 1.420(12) . ?
C7 O5 1.344(10) . ?
C8 H8 0.9500 . ?
C8 C9 1.423(11) . ?
C8 N3 1.286(9) . ?
C9 C10 1.397(12) . ?
C9 C20 1.406(12) . ?
C10 H10 0.9500 . ?
C10 C11 1.381(12) . ?
C11 C18 1.371(14) . ?
C11 N2 1.452(11) . ?
C12 C13 1.370(14) . ?
C12 C17 1.400(14) . ?
C12 N1 1.424(12) . ?
C13 H13 0.9500 . ?
C13 C14 1.389(14) . ?
C14 H14 0.9500 . ?
C14 C15 1.378(15) . ?
C15 H15 0.9500 . ?
C15 C16 1.366(17) . ?
C16 H16 0.9500 . ?
C16 C17 1.371(16) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
C18 C19 1.373(14) . ?
C19 H19 0.9500 . ?
C19 C20 1.411(12) . ?
C20 O2 1.327(9) . ?
N1 N2 1.233(10) . ?
N3 N4 1.416(8) . ?
N3 V1 2.124(6) . ?
O1 V1 1.970(5) . ?
O2 V1 1.910(5) . ?
O3 V1 1.603(5) . ?
O4 V1 1.639(5) . ?
O5 H5A 0.95(3) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C21 C22 1.457(15) . ?
C21 N5 1.487(12) . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
C23 H23A 0.9900 . ?
C23 H23B 0.9900 . ?
C23 C24 1.528(17) . ?
C23 N5 1.456(16) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 H25A 0.9900 . ?
C25 H25B 0.9900 . ?
C25 C26 1.456(18) . ?
C25 N5 1.538(13) . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
N5 H5B 0.90(3) . ?

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
N4 C1 C2 118.3(7) . . ?
O1 C1 C2 119.4(6) . . ?
O1 C1 N4 122.3(7) . . ?
C3 C2 C1 120.0(7) . . ?
C3 C2 C7 118.8(7) . . ?
C7 C2 C1 121.2(7) . . ?
C2 C3 H3 119.3 . . ?
C4 C3 C2 121.5(8) . . ?
C4 C3 H3 119.3 . . ?
C3 C4 H4 120.4 . . ?
C3 C4 C5 119.1(8) . . ?
C5 C4 H4 120.4 . . ?
C4 C5 H5 119.0 . . ?
C6 C5 C4 121.9(8) . . ?
C6 C5 H5 119.0 . . ?
C5 C6 H6 119.9 . . ?
C5 C6 C7 120.2(8) . . ?
C7 C6 H6 119.9 . . ?
C2 C7 C6 118.5(7) . . ?
O5 C7 C2 123.7(7) . . ?
O5 C7 C6 117.8(8) . . ?
C9 C8 H8 118.6 . . ?
N3 C8 H8 118.6 . . ?
N3 C8 C9 122.8(7) . . ?
C10 C9 C8 118.4(7) . . ?
C10 C9 C20 120.0(7) . . ?
C20 C9 C8 121.6(7) . . ?
C9 C10 H10 119.5 . . ?
C11 C10 C9 121.0(8) . . ?
C11 C10 H10 119.5 . . ?
C10 C11 N2 114.0(8) . . ?
C18 C11 C10 118.7(8) . . ?
C18 C11 N2 127.2(8) . . ?
C13 C12 C17 120.0(9) . . ?
C13 C12 N1 126.2(8) . . ?
C17 C12 N1 113.8(9) . . ?
C12 C13 H13 119.9 . . ?
C12 C13 C14 120.2(9) . . ?
C14 C13 H13 119.9 . . ?
C13 C14 H14 120.5 . . ?
C15 C14 C13 118.9(11) . . ?
C15 C14 H14 120.5 . . ?
C14 C15 H15 119.4 . . ?
C16 C15 C14 121.2(10) . . ?
C16 C15 H15 119.4 . . ?
C15 C16 H16 120.0 . . ?
C15 C16 C17 120.1(11) . . ?
C17 C16 H16 120.0 . . ?
C12 C17 H17 120.3 . . ?
C16 C17 C12 119.4(12) . . ?
C16 C17 H17 120.3 . . ?
C11 C18 H18 118.8 . . ?
C11 C18 C19 122.3(9) . . ?
C19 C18 H18 118.8 . . ?
C18 C19 H19 120.0 . . ?
C18 C19 C20 119.9(9) . . ?
C20 C19 H19 120.0 . . ?
C9 C20 C19 118.1(7) . . ?
O2 C20 C9 122.2(7) . . ?
O2 C20 C19 119.6(8) . . ?
N2 N1 C12 111.2(8) . . ?
N1 N2 C11 113.0(8) . . ?
C8 N3 N4 113.5(6) . . ?
C8 N3 V1 130.3(5) . . ?
N4 N3 V1 115.9(4) . . ?
C1 N4 N3 108.1(6) . . ?
C1 O1 V1 119.5(4) . . ?
C20 O2 V1 133.8(5) . . ?
C7 O5 H5A 109.5 . . ?
O1 V1 N3 73.9(2) . . ?
O2 V1 N3 81.2(2) . . ?
O2 V1 O1 149.1(2) . . ?
O3 V1 N3 109.0(3) . . ?
O3 V1 O1 101.4(3) . . ?
O3 V1 O2 103.8(3) . . ?
O3 V1 O4 109.1(3) . . ?
O4 V1 N3 141.5(3) . . ?
O4 V1 O1 93.3(2) . . ?
O4 V1 O2 95.1(3) . . ?
H21A C21 H21B 107.7 . . ?
C22 C21 H21A 108.9 . . ?
C22 C21 H21B 108.9 . . ?
C22 C21 N5 113.3(10) . . ?
N5 C21 H21A 108.9 . . ?
N5 C21 H21B 108.9 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
H23A C23 H23B 107.4 . . ?
C24 C23 H23A 108.4 . . ?
C24 C23 H23B 108.4 . . ?
N5 C23 H23A 108.4 . . ?
N5 C23 H23B 108.4 . . ?
N5 C23 C24 115.7(11) . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
H25A C25 H25B 107.8 . . ?
C26 C25 H25A 109.0 . . ?
C26 C25 H25B 109.0 . . ?
C26 C25 N5 113.0(10) . . ?
N5 C25 H25A 109.0 . . ?
N5 C25 H25B 109.0 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C21 N5 C25 106.8(8) . . ?
C21 N5 H5B 106.2 . . ?
C23 N5 C21 112.1(8) . . ?
C23 N5 C25 118.4(9) . . ?
C23 N5 H5B 106.2 . . ?
C25 N5 H5B 106.2 . . ?

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
O5 H5A N4 0.95 1.77 2.591(8) 142.2 . yes
N5 H5B O4 0.90 1.79 2.680(9) 169.3 . 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
C1 C2 C3 C4 -179.2(8) . . . . ?
C1 C2 C7 C6 178.5(8) . . . . ?
C1 C2 C7 O5 -2.2(13) . . . . ?
C2 C1 N4 N3 -179.6(6) . . . . ?
C2 C1 O1 V1 176.4(5) . . . . ?
C2 C3 C4 C5 -0.7(15) . . . . ?
C3 C2 C7 C6 -1.1(12) . . . . ?
C3 C2 C7 O5 178.2(8) . . . . ?
C3 C4 C5 C6 1.7(16) . . . . ?
C4 C5 C6 C7 -2.4(15) . . . . ?
C5 C6 C7 C2 2.1(13) . . . . ?
C5 C6 C7 O5 -177.3(8) . . . . ?
C7 C2 C3 C4 0.4(13) . . . . ?
C8 C9 C10 C11 177.9(8) . . . . ?
C8 C9 C20 C19 -176.8(8) . . . . ?
C8 C9 C20 O2 -1.2(12) . . . . ?
C8 N3 N4 C1 176.2(6) . . . . ?
C9 C8 N3 N4 177.6(7) . . . . ?
C9 C8 N3 V1 -9.4(11) . . . . ?
C9 C10 C11 C18 0.0(13) . . . . ?
C9 C10 C11 N2 176.3(8) . . . . ?
C9 C20 O2 V1 29.3(12) . . . . ?
C10 C9 C20 C19 2.5(11) . . . . ?
C10 C9 C20 O2 178.1(7) . . . . ?
C10 C11 C18 C19 0.2(15) . . . . ?
C10 C11 N2 N1 -173.7(8) . . . . ?
C11 C18 C19 C20 1.1(16) . . . . ?
C12 C13 C14 C15 -2.1(16) . . . . ?
C12 N1 N2 C11 -178.4(8) . . . . ?
C13 C12 C17 C16 5.5(17) . . . . ?
C13 C12 N1 N2 -7.7(14) . . . . ?
C13 C14 C15 C16 4.3(17) . . . . ?
C14 C15 C16 C17 -1.5(19) . . . . ?
C15 C16 C17 C12 -3.4(19) . . . . ?
C17 C12 C13 C14 -2.7(16) . . . . ?
C17 C12 N1 N2 174.1(9) . . . . ?
C18 C11 N2 N1 2.2(14) . . . . ?
C18 C19 C20 C9 -2.4(13) . . . . ?
C18 C19 C20 O2 -178.1(9) . . . . ?
C19 C20 O2 V1 -155.1(7) . . . . ?
C20 C9 C10 C11 -1.4(12) . . . . ?
N1 C12 C13 C14 179.2(10) . . . . ?
N1 C12 C17 C16 -176.2(11) . . . . ?
N2 C11 C18 C19 -175.6(10) . . . . ?
N3 C8 C9 C10 174.1(7) . . . . ?
N3 C8 C9 C20 -6.6(12) . . . . ?
N4 C1 C2 C3 173.6(8) . . . . ?
N4 C1 C2 C7 -6.0(12) . . . . ?
N4 C1 O1 V1 -4.4(10) . . . . ?
O1 C1 C2 C3 -7.2(12) . . . . ?
O1 C1 C2 C7 173.2(7) . . . . ?
O1 C1 N4 N3 1.2(10) . . . . ?
V1 N3 N4 C1 2.2(7) . . . . ?
C22 C21 N5 C23 57.4(13) . . . . ?
C22 C21 N5 C25 -171.3(11) . . . . ?
C24 C23 N5 C21 59.2(13) . . . . ?
C24 C23 N5 C25 -66.0(14) . . . . ?
C26 C25 N5 C21 163.7(10) . . . . ?
C26 C25 N5 C23 -68.6(13) . . . . ?

_olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems'
_olex2_exptl_crystal_mounting_method 'The crystal was mounted on a loop in oil'
_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_platon_pl
_database_code_depnum_ccdc_archive 'CCDC 1903090'
loop_
_audit_author_name
_audit_author_address
'Aurelien Crochet'
;University of Fribourg
Switzerland
;
_audit_update_record             
;
2019-03-13 deposited with the CCDC.	2019-06-27 downloaded from the CCDC.
;
_audit_creation_date             2019-03-13
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C20 H14 N4 O4 V, C6 H16 N'
_chemical_formula_sum            'C26 H30 N5 O4 V'
_chemical_formula_weight         527.49
_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'
V V 0.3005 0.5294 '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           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   6.9776(6)
_cell_length_b                   8.6271(7)
_cell_length_c                   22.0397(18)
_cell_angle_alpha                90
_cell_angle_beta                 94.002(7)
_cell_angle_gamma                90
_cell_volume                     1323.48(19)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    5736
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      23.42
_cell_measurement_theta_min      1.85
_shelx_estimated_absorpt_T_max   0.980
_shelx_estimated_absorpt_T_min   0.948
_exptl_absorpt_coefficient_mu    0.415
_exptl_absorpt_correction_T_max  0.9303
_exptl_absorpt_correction_T_min  0.7082
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   
;
STOE X-Red32, absorption correction by Gaussian integration, analogous to
P. Coppens, "The Evaluation of Absorption and Extinction in Single-Crystal
Structure Analysis", published in
F. R. Ahmed (Editor), "Crystallographic Computing",
Munksgaard, Copenhagen (1970), 255 - 270
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            orange
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.324
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             552
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.1554
_diffrn_reflns_av_unetI/netI     0.1311
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_number            17318
_diffrn_reflns_point_group_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.979
_diffrn_reflns_theta_full        25.214
_diffrn_reflns_theta_max         25.214
_diffrn_reflns_theta_min         2.536
_diffrn_ambient_temperature      298(2)
_diffrn_detector_area_resol_mean 6.67
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'STOE IPDS2'
_diffrn_measurement_method       'rotation method'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              'Stoe IPDS2'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.850
_reflns_Friedel_fraction_full    0.971
_reflns_Friedel_fraction_max     0.971
_reflns_number_gt                2275
_reflns_number_total             4684
_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       'X-Area (Stoe & Cie, 2009)'
_computing_data_collection       'X-Area (Stoe & Cie, 2009)'
_computing_data_reduction        'X-RED32(Stoe & Cie, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.249
_refine_diff_density_min         -0.367
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details 
;
 Flack x determined using 711 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(3)
_refine_ls_extinction_coef       0.0077(18)
_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   0.873
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     294
_refine_ls_number_reflns         4684
_refine_ls_number_restraints     66
_refine_ls_R_factor_all          0.1219
_refine_ls_R_factor_gt           0.0499
_refine_ls_restrained_S_all      0.873
_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)+(0.0374P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0919
_refine_ls_wR_factor_ref         0.1164
_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 C(H,H,H) groups
2. Restrained distances
 N5-H5A
 0.85 with sigma of 0.02
 N5-C21
 1.44 with sigma of 0.02
3. Rigid bond restraints
 C12, C13, C14, C15, C16, C17
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
 C25, C26, N5
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
C12 \\sim C13 \\sim C14 \\sim C15 \\sim C16 \\sim C17: within 1.7A with sigma
of 0.04 and sigma for terminal atoms of 0.08
C25 \\sim C26 \\sim N5: within 1.7A with sigma of 0.04 and sigma for terminal
atoms of 0.08
Uanis(C21) = Uanis(C25) = Uanis(C23)
Uanis(C22) = Uanis(C26) = Uanis(C24)
5.a Ternary CH refined with riding coordinates and stretchable bonds:
 N5(H5A)
5.b Secondary CH2 refined with riding coordinates:
 C21(H21A,H21B), C23(H23A,H23B), C25(H25A,H25B)
5.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C6(H6), C7(H7), C8(H8), C10(H10), C13(H13), C14(H14),
 C15(H15), C16(H16), C17(H17), C18(H18), C19(H19)
5.d Fitted hexagon refined as free rotating group:
 C2(C3,C4,C5,C6,C7)
5.e Idealised Me refined as rotating group:
 C22(H22A,H22B,H22C), C24(H24A,H24B,H24C), C26(H26A,H26B,H26C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.2142(12) 0.4827(8) 0.8789(3) 0.0597(18) Uani 1 1 d . . . . .
C2 C 0.2396(8) 0.5709(6) 0.93675(19) 0.069(2) Uani 1 1 d . . . . .
C3 C 0.0807(7) 0.5993(7) 0.9698(3) 0.089(3) Uani 1 1 d G . . . .
H3 H -0.038728 0.559276 0.956561 0.107 Uiso 1 1 calc R . . . .
C4 C 0.1004(8) 0.6874(8) 1.0227(3) 0.101(3) Uani 1 1 d G . . . .
H4 H -0.005879 0.706330 1.044805 0.121 Uiso 1 1 calc R . . . .
C5 C 0.2789(10) 0.7471(7) 1.0425(2) 0.098(3) Uani 1 1 d G . . . .
H5 H 0.292093 0.806053 1.077864 0.117 Uiso 1 1 calc R . . . .
C6 C 0.4378(7) 0.7187(7) 1.0094(3) 0.093(3) Uani 1 1 d G . . . .
H6 H 0.557218 0.758722 1.022680 0.112 Uiso 1 1 calc R . . . .
C7 C 0.4181(7) 0.6306(7) 0.9566(2) 0.076(2) Uani 1 1 d G . . . .
H7 H 0.524374 0.611667 0.934435 0.091 Uiso 1 1 calc R . . . .
C8 C 0.4254(11) 0.3665(8) 0.7547(3) 0.059(2) Uani 1 1 d . . . . .
H8 H 0.545923 0.410632 0.763244 0.071 Uiso 1 1 calc R . . . .
C9 C 0.3902(10) 0.2794(8) 0.6995(3) 0.061(2) Uani 1 1 d . . . . .
C10 C 0.5332(11) 0.2797(11) 0.6580(3) 0.076(3) Uani 1 1 d . . . . .
H10 H 0.644874 0.336807 0.666559 0.091 Uiso 1 1 calc R . . . .
C11 C 0.5106(12) 0.1967(11) 0.6050(4) 0.075(2) Uani 1 1 d . . . . .
C12 C 0.7929(13) 0.1599(11) 0.4780(4) 0.079(2) Uani 1 1 d . U . . .
C13 C 0.9534(13) 0.2501(12) 0.4905(4) 0.094(3) Uani 1 1 d . U . . .
H13 H 0.962841 0.312650 0.524943 0.113 Uiso 1 1 calc R . . . .
C14 C 1.0994(14) 0.2475(13) 0.4520(4) 0.111(4) Uani 1 1 d . U . . .
H14 H 1.209409 0.306492 0.460681 0.133 Uiso 1 1 calc R . . . .
C15 C 1.0825(17) 0.1571(14) 0.4005(5) 0.110(3) Uani 1 1 d . U . . .
H15 H 1.183024 0.153293 0.374929 0.132 Uiso 1 1 calc R . . . .
C16 C 0.9197(18) 0.0728(15) 0.3864(5) 0.117(4) Uani 1 1 d . U . . .
H16 H 0.906791 0.013930 0.350977 0.140 Uiso 1 1 calc R . . . .
C17 C 0.7784(15) 0.0769(13) 0.4249(4) 0.101(3) Uani 1 1 d . U . . .
H17 H 0.666450 0.021215 0.415048 0.121 Uiso 1 1 calc R . . . .
C18 C 0.3438(13) 0.1076(11) 0.5923(4) 0.083(3) Uani 1 1 d . . . . .
H18 H 0.329183 0.049346 0.556799 0.100 Uiso 1 1 calc R . . . .
C19 C 0.2034(12) 0.1073(11) 0.6326(4) 0.082(3) Uani 1 1 d . . . . .
H19 H 0.093671 0.047696 0.624128 0.098 Uiso 1 1 calc R . . . .
C20 C 0.2209(12) 0.1941(9) 0.6859(3) 0.067(2) Uani 1 1 d . . . . .
N1 N 0.3569(9) 0.4722(8) 0.8442(3) 0.0656(17) Uani 1 1 d . . . . .
N2 N 0.2952(8) 0.3856(7) 0.7929(3) 0.0599(16) Uani 1 1 d . . . . .
N3 N 0.6644(10) 0.2112(9) 0.5648(3) 0.084(2) Uani 1 1 d . . . . .
N4 N 0.6352(10) 0.1459(9) 0.5156(3) 0.089(2) Uani 1 1 d . . . . .
O1 O 0.0483(8) 0.4175(6) 0.8657(2) 0.0713(14) Uani 1 1 d . . . . .
O2 O 0.0823(7) 0.1856(6) 0.7251(2) 0.0739(15) Uani 1 1 d . . . . .
O3 O -0.1163(7) 0.4565(6) 0.7481(2) 0.0708(14) Uani 1 1 d . . . . .
O4 O -0.1560(8) 0.1964(6) 0.8103(2) 0.0830(16) Uani 1 1 d . . . . .
V1 V -0.00257(16) 0.32117(14) 0.78586(5) 0.0616(4) Uani 1 1 d . . . . .
C21 C -0.1480(17) -0.2046(13) 0.8158(5) 0.125(2) Uani 1 1 d D . . . .
H21A H -0.093248 -0.186313 0.856876 0.151 Uiso 1 1 calc R . . . .
H21B H -0.201871 -0.308257 0.814323 0.151 Uiso 1 1 calc R . . . .
C22 C 0.0071(15) -0.1941(16) 0.7725(6) 0.153(3) Uani 1 1 d . . . . .
H22A H -0.044977 -0.218676 0.732208 0.229 Uiso 1 1 calc GR . . . .
H22B H 0.107664 -0.266075 0.784481 0.229 Uiso 1 1 calc GR . . . .
H22C H 0.058280 -0.090753 0.773071 0.229 Uiso 1 1 calc GR . . . .
C23 C -0.3810(18) -0.0911(12) 0.7373(6) 0.125(2) Uani 1 1 d . . . . .
H23A H -0.276345 -0.069842 0.711700 0.151 Uiso 1 1 calc R . . . .
H23B H -0.474533 -0.008522 0.730806 0.151 Uiso 1 1 calc R . . . .
C24 C -0.4745(18) -0.2429(13) 0.7172(7) 0.153(3) Uani 1 1 d . . . . .
H24A H -0.379948 -0.323888 0.719514 0.229 Uiso 1 1 calc GR . . . .
H24B H -0.528039 -0.233367 0.676037 0.229 Uiso 1 1 calc GR . . . .
H24C H -0.574710 -0.267503 0.743296 0.229 Uiso 1 1 calc GR . . . .
C25 C -0.4373(17) -0.1073(13) 0.8496(5) 0.125(2) Uani 1 1 d . U . . .
H25A H -0.500839 -0.206842 0.844352 0.151 Uiso 1 1 calc R . . . .
H25B H -0.361481 -0.110067 0.888201 0.151 Uiso 1 1 calc R . . . .
C26 C -0.5836(16) 0.0117(15) 0.8530(7) 0.153(3) Uani 1 1 d . U . . .
H26A H -0.523295 0.109656 0.862317 0.229 Uiso 1 1 calc GR . . . .
H26B H -0.667018 -0.014603 0.884308 0.229 Uiso 1 1 calc GR . . . .
H26C H -0.657297 0.018599 0.814658 0.229 Uiso 1 1 calc GR . . . .
N5 N -0.3060(12) -0.0882(9) 0.8008(4) 0.098(2) Uani 1 1 d D U . . .
H5A H -0.254(2) 0.002(3) 0.8065(4) 0.118 Uiso 1 1 calc DGR . . . .


_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 C2 1.485(8) . ?
C1 N1 1.300(9) . ?
C1 O1 1.302(8) . ?
C2 C3 1.3900 . ?
C2 C7 1.3900 . ?
C3 H3 0.9300 . ?
C3 C4 1.3900 . ?
C4 H4 0.9300 . ?
C4 C5 1.3900 . ?
C5 H5 0.9300 . ?
C5 C6 1.3900 . ?
C6 H6 0.9300 . ?
C6 C7 1.3900 . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
C8 C9 1.437(9) . ?
C8 N2 1.291(8) . ?
C9 C10 1.399(11) . ?
C9 C20 1.406(10) . ?
C10 H10 0.9300 . ?
C10 C11 1.370(10) . ?
C11 C18 1.406(12) . ?
C11 N3 1.445(10) . ?
C12 C13 1.376(12) . ?
C12 C17 1.370(12) . ?
C12 N4 1.427(10) . ?
C13 H13 0.9300 . ?
C13 C14 1.370(12) . ?
C14 H14 0.9300 . ?
C14 C15 1.376(13) . ?
C15 H15 0.9300 . ?
C15 C16 1.366(15) . ?
C16 H16 0.9300 . ?
C16 C17 1.345(12) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C18 C19 1.367(11) . ?
C19 H19 0.9300 . ?
C19 C20 1.392(10) . ?
C20 O2 1.343(8) . ?
N1 N2 1.398(8) . ?
N2 V1 2.146(6) . ?
N3 N4 1.226(8) . ?
O1 V1 1.956(5) . ?
O2 V1 1.903(5) . ?
O3 V1 1.610(5) . ?
O4 V1 1.636(5) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C21 C22 1.495(14) . ?
C21 N5 1.511(11) . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C23 C24 1.515(15) . ?
C23 N5 1.461(13) . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 H25A 0.9700 . ?
C25 H25B 0.9700 . ?
C25 C26 1.453(15) . ?
C25 N5 1.470(12) . ?
C26 H26A 0.9600 . ?
C26 H26B 0.9600 . ?
C26 H26C 0.9600 . ?
N5 H5A 0.86(3) . ?

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
N1 C1 C2 119.4(7) . . ?
N1 C1 O1 123.0(6) . . ?
O1 C1 C2 117.7(6) . . ?
C3 C2 C1 119.3(5) . . ?
C3 C2 C7 120.0 . . ?
C7 C2 C1 120.7(5) . . ?
C2 C3 H3 120.0 . . ?
C2 C3 C4 120.0 . . ?
C4 C3 H3 120.0 . . ?
C3 C4 H4 120.0 . . ?
C3 C4 C5 120.0 . . ?
C5 C4 H4 120.0 . . ?
C4 C5 H5 120.0 . . ?
C6 C5 C4 120.0 . . ?
C6 C5 H5 120.0 . . ?
C5 C6 H6 120.0 . . ?
C7 C6 C5 120.0 . . ?
C7 C6 H6 120.0 . . ?
C2 C7 H7 120.0 . . ?
C6 C7 C2 120.0 . . ?
C6 C7 H7 120.0 . . ?
C9 C8 H8 118.9 . . ?
N2 C8 H8 118.9 . . ?
N2 C8 C9 122.1(7) . . ?
C10 C9 C8 117.7(7) . . ?
C10 C9 C20 119.2(7) . . ?
C20 C9 C8 123.1(7) . . ?
C9 C10 H10 119.6 . . ?
C11 C10 C9 120.7(7) . . ?
C11 C10 H10 119.6 . . ?
C10 C11 C18 120.0(7) . . ?
C10 C11 N3 115.6(8) . . ?
C18 C11 N3 124.4(8) . . ?
C13 C12 N4 125.5(8) . . ?
C17 C12 C13 118.5(8) . . ?
C17 C12 N4 116.0(9) . . ?
C12 C13 H13 120.1 . . ?
C14 C13 C12 119.8(9) . . ?
C14 C13 H13 120.1 . . ?
C13 C14 H14 120.1 . . ?
C13 C14 C15 119.7(10) . . ?
C15 C14 H14 120.1 . . ?
C14 C15 H15 119.6 . . ?
C16 C15 C14 120.7(10) . . ?
C16 C15 H15 119.6 . . ?
C15 C16 H16 120.8 . . ?
C17 C16 C15 118.5(11) . . ?
C17 C16 H16 120.8 . . ?
C12 C17 H17 118.7 . . ?
C16 C17 C12 122.6(10) . . ?
C16 C17 H17 118.7 . . ?
C11 C18 H18 120.2 . . ?
C19 C18 C11 119.5(8) . . ?
C19 C18 H18 120.2 . . ?
C18 C19 H19 119.3 . . ?
C18 C19 C20 121.5(8) . . ?
C20 C19 H19 119.3 . . ?
C19 C20 C9 119.0(7) . . ?
O2 C20 C9 121.5(7) . . ?
O2 C20 C19 119.3(8) . . ?
C1 N1 N2 107.9(6) . . ?
C8 N2 N1 113.9(6) . . ?
C8 N2 V1 129.9(5) . . ?
N1 N2 V1 116.0(4) . . ?
N4 N3 C11 114.7(7) . . ?
N3 N4 C12 112.8(7) . . ?
C1 O1 V1 119.2(4) . . ?
C20 O2 V1 133.8(5) . . ?
O1 V1 N2 73.2(2) . . ?
O2 V1 N2 82.1(2) . . ?
O2 V1 O1 148.0(2) . . ?
O3 V1 N2 106.8(2) . . ?
O3 V1 O1 102.0(3) . . ?
O3 V1 O2 104.4(3) . . ?
O3 V1 O4 109.7(3) . . ?
O4 V1 N2 143.1(3) . . ?
O4 V1 O1 93.7(2) . . ?
O4 V1 O2 94.0(3) . . ?
H21A C21 H21B 107.9 . . ?
C22 C21 H21A 109.3 . . ?
C22 C21 H21B 109.3 . . ?
C22 C21 N5 111.7(10) . . ?
N5 C21 H21A 109.3 . . ?
N5 C21 H21B 109.3 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
H23A C23 H23B 107.6 . . ?
C24 C23 H23A 108.7 . . ?
C24 C23 H23B 108.7 . . ?
N5 C23 H23A 108.7 . . ?
N5 C23 H23B 108.7 . . ?
N5 C23 C24 114.4(10) . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
H25A C25 H25B 107.4 . . ?
C26 C25 H25A 108.3 . . ?
C26 C25 H25B 108.3 . . ?
C26 C25 N5 115.8(10) . . ?
N5 C25 H25A 108.3 . . ?
N5 C25 H25B 108.3 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C21 N5 H5A 105.8 . . ?
C23 N5 C21 113.9(8) . . ?
C23 N5 C25 120.0(9) . . ?
C23 N5 H5A 105.8 . . ?
C25 N5 C21 104.3(8) . . ?
C25 N5 H5A 105.8 . . ?

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 H5A O4 0.86 1.81 2.671(9) 173.8 . 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
C1 C2 C3 C4 -177.2(5) . . . . ?
C1 C2 C7 C6 177.2(5) . . . . ?
C1 N1 N2 C8 -179.8(6) . . . . ?
C1 N1 N2 V1 4.9(7) . . . . ?
C2 C1 N1 N2 -179.3(6) . . . . ?
C2 C1 O1 V1 172.8(4) . . . . ?
C2 C3 C4 C5 0.0 . . . . ?
C3 C2 C7 C6 0.0 . . . . ?
C3 C4 C5 C6 0.0 . . . . ?
C4 C5 C6 C7 0.0 . . . . ?
C5 C6 C7 C2 0.0 . . . . ?
C7 C2 C3 C4 0.0 . . . . ?
C8 C9 C10 C11 178.8(7) . . . . ?
C8 C9 C20 C19 -177.0(7) . . . . ?
C8 C9 C20 O2 -1.9(11) . . . . ?
C9 C8 N2 N1 179.3(6) . . . . ?
C9 C8 N2 V1 -6.2(10) . . . . ?
C9 C10 C11 C18 -1.2(13) . . . . ?
C9 C10 C11 N3 177.5(7) . . . . ?
C9 C20 O2 V1 29.4(11) . . . . ?
C10 C9 C20 C19 2.5(11) . . . . ?
C10 C9 C20 O2 177.6(7) . . . . ?
C10 C11 C18 C19 1.4(14) . . . . ?
C10 C11 N3 N4 -174.6(8) . . . . ?
C11 C18 C19 C20 0.4(14) . . . . ?
C11 N3 N4 C12 -178.4(7) . . . . ?
C12 C13 C14 C15 1.4(15) . . . . ?
C13 C12 C17 C16 4.1(16) . . . . ?
C13 C12 N4 N3 -7.2(13) . . . . ?
C13 C14 C15 C16 1.7(17) . . . . ?
C14 C15 C16 C17 -1.8(19) . . . . ?
C15 C16 C17 C12 -1.2(18) . . . . ?
C17 C12 C13 C14 -4.1(14) . . . . ?
C17 C12 N4 N3 173.7(8) . . . . ?
C18 C11 N3 N4 4.1(13) . . . . ?
C18 C19 C20 C9 -2.3(13) . . . . ?
C18 C19 C20 O2 -177.5(8) . . . . ?
C19 C20 O2 V1 -155.5(6) . . . . ?
C20 C9 C10 C11 -0.7(12) . . . . ?
N1 C1 C2 C3 171.7(5) . . . . ?
N1 C1 C2 C7 -5.5(8) . . . . ?
N1 C1 O1 V1 -7.9(9) . . . . ?
N2 C8 C9 C10 173.1(7) . . . . ?
N2 C8 C9 C20 -7.4(11) . . . . ?
N3 C11 C18 C19 -177.2(9) . . . . ?
N4 C12 C13 C14 176.8(9) . . . . ?
N4 C12 C17 C16 -176.7(10) . . . . ?
O1 C1 C2 C3 -9.1(8) . . . . ?
O1 C1 C2 C7 173.7(5) . . . . ?
O1 C1 N1 N2 1.4(10) . . . . ?
C22 C21 N5 C23 51.0(13) . . . . ?
C22 C21 N5 C25 -176.3(9) . . . . ?
C24 C23 N5 C21 62.5(13) . . . . ?
C24 C23 N5 C25 -62.2(13) . . . . ?
C26 C25 N5 C21 168.5(11) . . . . ?
C26 C25 N5 C23 -62.4(13) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
