# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2017

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

data_N-Me-Eu-hV-GPC-new1
_database_code_depnum_ccdc_archive 'CCDC 1546704'
_audit_update_record             
;
2017-04-27 deposited with the CCDC.
2017-05-31 downloaded from the CCDC.
;

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

_chemical_formula_sum            'C13 H14 N2 O3'
_chemical_formula_moiety         'C13 H14 N2 O3'
_chemical_formula_weight         246.27
_chemical_melting_point          ?

#==============================================================================
# CRYSTAL DATA
_space_group_crystal_system      triclinic
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
_space_group_IT_number           2
loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 +X,+Y,+Z
2 -X,-Y,-Z
#------------------------------------------------------------------------------
_cell_length_a                   7.1986(3)
_cell_length_b                   8.6106(4)
_cell_length_c                   20.1002(8)
_cell_angle_alpha                89.502(6)
_cell_angle_beta                 82.040(6)
_cell_angle_gamma                89.728(6)
_cell_volume                     1233.83(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    13140
_cell_measurement_theta_min      3.07
_cell_measurement_theta_max      25.37
_cell_measurement_temperature    123
#------------------------------------------------------------------------------
_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.090
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.040
_exptl_crystal_density_diffrn    1.326
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             520.00
_exptl_absorpt_coefficient_mu    0.096
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'ABSCOR (Rigaku, 1995)'
_exptl_absorpt_correction_T_min  0.801
_exptl_absorpt_correction_T_max  0.996

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

_diffrn_ambient_temperature      123
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71075
_diffrn_measurement_device_type  'Rigaku R-AXIS RAPID'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.000
_diffrn_reflns_number            17033
_diffrn_reflns_av_R_equivalents  0.0323
_diffrn_reflns_theta_max         25.345
_diffrn_reflns_theta_min         3.070
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_standards_number         0
_diffrn_standards_interval_count .
_diffrn_standards_decay_%        ?
_reflns_number_total             4530
_reflns_number_gt                3860
_reflns_threshold_expression     F²>2.0σ(F²)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

#==============================================================================
# REFINEMENT DATA

_refine_special_details          
;
    Refinement was performed using all reflections. The weighted 
    R-factor (wR) and goodness of fit (S) are based on F².
    R-factor (gt) are based on F. The threshold expression of
    F² > 2.0 sigma(F²) is used only for calculating R-factor (gt).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_R_factor_all          0.1032
_refine_ls_R_factor_gt           0.0907
_refine_ls_wR_factor_ref         0.1768
_refine_ls_wR_factor_gt          0.1713
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_number_reflns         4530
_refine_ls_number_parameters     405
_refine_ls_goodness_of_fit_ref   1.119
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w = 1/[σ²(Fo²)+(0.0014P)²+3.9726P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_refine_ls_shift/su_max          0.000
_refine_diff_density_max         0.77
_refine_diff_density_min         -0.60
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

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 for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.0000 0.0000
;
International Tables for Crystallography
(Vol. C, Table 6.1.1.4)
;
N N 0.0061 0.0033
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
O O 0.0106 0.0060
;
International Tables for Crystallography
(Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;

#==============================================================================
# ATOMIC COORDINATES AND THERMAL 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
O1 O 0.6896(4) 0.8164(3) 0.11942(15) 0.0464(8) Uani 1 1 d . . . . .
O2 O 0.7749(4) 0.6120(3) -0.00615(12) 0.0334(6) Uani 1 1 d . . . . .
H2A H 0.6607 0.5928 -0.0065 0.040 Uiso 1 1 calc R U . . .
O3 O 0.5264(4) 0.4619(4) 0.08025(13) 0.0417(7) Uani 1 1 d . . . . .
O4 O 0.4702(5) -0.0484(7) 0.42277(17) 0.110(2) Uani 1 1 d . . . . .
O5 O 0.2210(4) 0.1003(4) 0.51046(13) 0.0472(8) Uani 1 1 d . . . . .
H5 H 0.3359 0.0854 0.5118 0.057 Uiso 1 1 calc R U . . .
O6A O 0.3962(10) 0.2780(7) 0.3975(3) 0.0359(18) Uani 0.448(6) 1 d . . P A 1
C20A C 0.2348(17) 0.2406(15) 0.4153(6) 0.022(3) Uani 0.448(6) 1 d . . P A 1
C21A C 0.068(3) 0.3372(15) 0.4155(6) 0.021(3) Uani 0.448(6) 1 d . . P A 1
C22A C -0.119(2) 0.3070(19) 0.4361(7) 0.025(4) Uani 0.448(6) 1 d . . P A 1
H22A H -0.1718 0.2102 0.4515 0.030 Uiso 0.448(6) 1 calc R U P A 1
C23A C -0.214(2) 0.4461(14) 0.4301(5) 0.042(3) Uani 0.448(6) 1 d . . P A 1
H23A H -0.3456 0.4626 0.4402 0.050 Uiso 0.448(6) 1 calc R U P A 1
C24A C -0.084(3) 0.553(2) 0.4069(8) 0.042(5) Uani 0.448(6) 1 d . . P A 1
H24A H -0.1123 0.6589 0.3985 0.050 Uiso 0.448(6) 1 calc R U P A 1
N4A N 0.0866(11) 0.4951(8) 0.3975(3) 0.0297(19) Uani 0.448(6) 1 d . . P A 1
C26A C 0.2549(14) 0.5789(9) 0.3704(5) 0.037(2) Uani 0.448(6) 1 d . . P A 1
H26A H 0.2203 0.6813 0.3543 0.045 Uiso 0.448(6) 1 calc R U P A 1
H26B H 0.3230 0.5204 0.3331 0.045 Uiso 0.448(6) 1 calc R U P A 1
H26C H 0.3350 0.5915 0.4056 0.045 Uiso 0.448(6) 1 calc R U P A 1
O6B O 0.2865(8) 0.3388(7) 0.3836(3) 0.0390(15) Uani 0.552(6) 1 d . . P A 2
C20B C 0.1491(19) 0.2739(15) 0.4143(4) 0.028(3) Uani 0.552(6) 1 d . . P A 2
C21B C -0.038(2) 0.3393(13) 0.4304(6) 0.023(3) Uani 0.552(6) 1 d . . P A 2
C22B C -0.2044(14) 0.2700(12) 0.4524(5) 0.030(2) Uani 0.552(6) 1 d . . P A 2
H22B H -0.2220 0.1627 0.4626 0.037 Uiso 0.552(6) 1 calc R U P A 2
C23B C -0.3451(11) 0.3822(9) 0.4574(4) 0.0351(18) Uani 0.552(6) 1 d . . P A 2
H23B H -0.4754 0.3665 0.4709 0.042 Uiso 0.552(6) 1 calc R U P A 2
C24B C -0.2567(13) 0.5212(11) 0.4387(4) 0.035(2) Uani 0.552(6) 1 d . . P A 2
H24B H -0.3186 0.6187 0.4373 0.042 Uiso 0.552(6) 1 calc R U P A 2
N4B N -0.0717(17) 0.4991(13) 0.4227(5) 0.034(2) Uani 0.552(6) 1 d . . P A 2
C26B C 0.0645(13) 0.6210(9) 0.3986(4) 0.040(2) Uani 0.552(6) 1 d . . P A 2
H26D H 0.1108 0.6046 0.3510 0.048 Uiso 0.552(6) 1 calc R U P A 2
H26E H 0.1698 0.6167 0.4247 0.048 Uiso 0.552(6) 1 calc R U P A 2
H26F H 0.0034 0.7230 0.4042 0.048 Uiso 0.552(6) 1 calc R U P A 2
N1 N 1.0388(5) 0.9903(4) 0.08389(15) 0.0376(8) Uani 1 1 d . . . . .
N2 N 0.5961(5) 0.3642(4) 0.21505(16) 0.0416(9) Uani 1 1 d . . . . .
N3 N 0.4076(5) -0.1250(6) 0.28652(17) 0.0588(12) Uani 1 1 d . . . . .
C1 C 1.2240(6) 1.0186(5) 0.0683(2) 0.0422(10) Uani 1 1 d . . . . .
H1 H 1.2795 1.1184 0.0687 0.051 Uiso 1 1 calc R U . . .
C2 C 1.3195(6) 0.8865(5) 0.0521(2) 0.0430(10) Uani 1 1 d . . . . .
H2 H 1.4513 0.8764 0.0398 0.052 Uiso 1 1 calc R U . . .
C3 C 1.1868(6) 0.7661(5) 0.05672(19) 0.0350(9) Uani 1 1 d . . . . .
H3 H 1.2124 0.6593 0.0479 0.042 Uiso 1 1 calc R U . . .
C4 C 1.0118(6) 0.8318(4) 0.07661(17) 0.0307(8) Uani 1 1 d . . . . .
C5 C 0.8318(5) 0.7559(4) 0.08974(17) 0.0311(8) Uani 1 1 d . . . . .
C6 C 0.8196(5) 0.5920(4) 0.06021(17) 0.0277(8) Uani 1 1 d . . . . .
H6 H 0.9443 0.5392 0.0582 0.033 Uiso 1 1 calc R U . . .
C7 C 0.6710(5) 0.4950(4) 0.10352(18) 0.0284(8) Uani 1 1 d . . . . .
C8 C 0.7159(5) 0.4459(4) 0.16800(18) 0.0294(8) Uani 1 1 d . . . . .
C9 C 0.8818(5) 0.4673(4) 0.19449(19) 0.0317(8) Uani 1 1 d . . . . .
H9 H 0.9899 0.5202 0.1733 0.038 Uiso 1 1 calc R U . . .
C10 C 0.8615(6) 0.3977(5) 0.2574(2) 0.0393(10) Uani 1 1 d . . . . .
H10 H 0.9534 0.3941 0.2871 0.047 Uiso 1 1 calc R U . . .
C11 C 0.6849(7) 0.3349(5) 0.2693(2) 0.0460(11) Uani 1 1 d . . . . .
H11 H 0.6335 0.2801 0.3088 0.055 Uiso 1 1 calc R U . . .
C12 C 0.8965(8) 1.1057(5) 0.1043(2) 0.0530(13) Uani 1 1 d . . . . .
H12A H 0.9494 1.2097 0.0952 0.064 Uiso 1 1 calc R U . . .
H12B H 0.8527 1.0941 0.1524 0.064 Uiso 1 1 calc R U . . .
H12C H 0.7909 1.0917 0.0789 0.064 Uiso 1 1 calc R U . . .
C13 C 0.4051(7) 0.3151(8) 0.2095(3) 0.0755(19) Uani 1 1 d . . . . .
H13A H 0.4083 0.2346 0.1753 0.091 Uiso 1 1 calc R U . . .
H13B H 0.3324 0.4044 0.1968 0.091 Uiso 1 1 calc R U . . .
H13C H 0.3464 0.2736 0.2529 0.091 Uiso 1 1 calc R U . . .
C14 C 0.3189(6) -0.1494(6) 0.2325(2) 0.0465(11) Uani 1 1 d . . . . .
H14 H 0.3716 -0.2006 0.1925 0.056 Uiso 1 1 calc R U . . .
C15 C 0.1419(6) -0.0892(5) 0.24428(19) 0.0355(9) Uani 1 1 d . . . . .
H15 H 0.0504 -0.0914 0.2145 0.043 Uiso 1 1 calc R U . . .
C16 C 0.1198(5) -0.0236(4) 0.30825(18) 0.0296(8) Uani 1 1 d . . . . .
H16 H 0.0110 0.0279 0.3297 0.036 Uiso 1 1 calc R U . . .
C17 C 0.2865(5) -0.0476(6) 0.33464(19) 0.0400(10) Uani 1 1 d . . . . .
C18 C 0.3296(6) -0.0080(7) 0.4002(2) 0.0544(14) Uani 1 1 d . . . . .
C19 C 0.1846(6) 0.0904(5) 0.44334(18) 0.0358(9) Uani 1 1 d . . . . .
H19 H 0.0524 0.0606 0.4395 0.043 Uiso 1 1 calc R U . A 1
C25 C 0.5993(8) -0.1778(12) 0.2917(3) 0.129(4) Uani 1 1 d . . . . .
H25A H 0.5961 -0.2562 0.3275 0.154 Uiso 1 1 calc R U . . .
H25B H 0.6751 -0.0893 0.3022 0.154 Uiso 1 1 calc R U . . .
H25C H 0.6548 -0.2231 0.2489 0.154 Uiso 1 1 calc R U . . .


#==============================================================================
_computing_data_collection       'RAPID AUTO (Rigaku, ????)'
_computing_cell_refinement       'RAPID AUTO'
_computing_data_reduction        'RAPID AUTO'
_computing_structure_solution    'SIR2011 (Burla, et al., 2012)'
_computing_structure_refinement  'SHELXL Version 2014/7 (Sheldrick, 2008)'
_computing_publication_material  'CrystalStructure 4.2 (Rigaku, 2015)'
_computing_molecular_graphics    'CrystalStructure 4.2'

#==============================================================================
# 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
O1 C5 1.227(4) . ?
O2 C6 1.424(4) . ?
O2 H2A 0.8400 . ?
O3 C7 1.234(4) . ?
O4 C18 1.212(5) . ?
O5 C19 1.413(4) . ?
O5 H5 0.8400 . ?
O6A C20A 1.212(14) . ?
C20A C19 1.434(14) . ?
C20A C21A 1.460(15) . ?
C21A C22A 1.373(16) . ?
C21A N4A 1.406(15) . ?
C22A C23A 1.391(19) . ?
C22A H22A 0.9500 . ?
C23A C24A 1.35(2) . ?
C23A H23A 0.9500 . ?
C24A N4A 1.31(2) . ?
C24A H24A 0.9500 . ?
N4A C26A 1.450(12) . ?
C26A H26A 0.9800 . ?
C26A H26B 0.9800 . ?
C26A H26C 0.9800 . ?
O6B C20B 1.226(12) . ?
C20B C21B 1.450(15) . ?
C20B C19 1.710(14) . ?
C21B C22B 1.360(13) . ?
C21B N4B 1.407(16) . ?
C22B C23B 1.390(12) . ?
C22B H22B 0.9500 . ?
C23B C24B 1.383(12) . ?
C23B H23B 0.9500 . ?
C24B N4B 1.340(16) . ?
C24B H24B 0.9500 . ?
N4B C26B 1.472(13) . ?
C26B H26D 0.9800 . ?
C26B H26E 0.9800 . ?
C26B H26F 0.9800 . ?
N1 C1 1.349(6) . ?
N1 C4 1.392(5) . ?
N1 C12 1.444(5) . ?
N2 C11 1.360(5) . ?
N2 C8 1.379(5) . ?
N2 C13 1.459(5) . ?
N3 C14 1.353(5) . ?
N3 C17 1.383(5) . ?
N3 C25 1.468(6) . ?
C1 C2 1.345(6) . ?
C1 H1 0.9500 . ?
C2 C3 1.407(6) . ?
C2 H2 0.9500 . ?
C3 C4 1.387(6) . ?
C3 H3 0.9500 . ?
C4 C5 1.444(6) . ?
C5 C6 1.544(5) . ?
C6 C7 1.529(5) . ?
C6 H6 1.0000 . ?
C7 C8 1.438(5) . ?
C8 C9 1.387(5) . ?
C9 C10 1.385(5) . ?
C9 H9 0.9500 . ?
C10 C11 1.373(6) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.364(6) . ?
C14 H14 0.9500 . ?
C15 C16 1.397(5) . ?
C15 H15 0.9500 . ?
C16 C17 1.391(5) . ?
C16 H16 0.9500 . ?
C17 C18 1.440(5) . ?
C18 C19 1.521(6) . ?
C19 H19 1.0000 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 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
C6 O2 H2A 109.5 . . ?
C19 O5 H5 109.5 . . ?
O6A C20A C19 122.5(11) . . ?
O6A C20A C21A 127.3(14) . . ?
C19 C20A C21A 110.2(11) . . ?
C22A C21A N4A 108.6(15) . . ?
C22A C21A C20A 131.6(16) . . ?
N4A C21A C20A 119.7(14) . . ?
C21A C22A C23A 106.5(17) . . ?
C21A C22A H22A 126.8 . . ?
C23A C22A H22A 126.8 . . ?
C24A C23A C22A 106.7(14) . . ?
C24A C23A H23A 126.6 . . ?
C22A C23A H23A 126.6 . . ?
N4A C24A C23A 112.4(14) . . ?
N4A C24A H24A 123.8 . . ?
C23A C24A H24A 123.8 . . ?
C24A N4A C21A 105.8(13) . . ?
C24A N4A C26A 125.5(11) . . ?
C21A N4A C26A 128.6(10) . . ?
N4A C26A H26A 109.5 . . ?
N4A C26A H26B 109.5 . . ?
H26A C26A H26B 109.5 . . ?
N4A C26A H26C 109.5 . . ?
H26A C26A H26C 109.5 . . ?
H26B C26A H26C 109.5 . . ?
O6B C20B C21B 126.5(13) . . ?
O6B C20B C19 116.3(11) . . ?
C21B C20B C19 117.2(8) . . ?
C22B C21B N4B 107.8(13) . . ?
C22B C21B C20B 130.7(13) . . ?
N4B C21B C20B 121.5(13) . . ?
C21B C22B C23B 108.7(11) . . ?
C21B C22B H22B 125.6 . . ?
C23B C22B H22B 125.6 . . ?
C24B C23B C22B 106.0(8) . . ?
C24B C23B H23B 127.0 . . ?
C22B C23B H23B 127.0 . . ?
N4B C24B C23B 110.4(10) . . ?
N4B C24B H24B 124.8 . . ?
C23B C24B H24B 124.8 . . ?
C24B N4B C21B 107.0(11) . . ?
C24B N4B C26B 125.0(10) . . ?
C21B N4B C26B 127.9(12) . . ?
N4B C26B H26D 109.5 . . ?
N4B C26B H26E 109.5 . . ?
H26D C26B H26E 109.5 . . ?
N4B C26B H26F 109.5 . . ?
H26D C26B H26F 109.5 . . ?
H26E C26B H26F 109.5 . . ?
C1 N1 C4 107.7(4) . . ?
C1 N1 C12 125.4(4) . . ?
C4 N1 C12 126.9(4) . . ?
C11 N2 C8 108.7(3) . . ?
C11 N2 C13 124.1(4) . . ?
C8 N2 C13 127.1(3) . . ?
C14 N3 C17 108.6(4) . . ?
C14 N3 C25 124.1(4) . . ?
C17 N3 C25 127.3(4) . . ?
C2 C1 N1 110.9(4) . . ?
C2 C1 H1 124.5 . . ?
N1 C1 H1 124.5 . . ?
C1 C2 C3 106.8(4) . . ?
C1 C2 H2 126.6 . . ?
C3 C2 H2 126.6 . . ?
C4 C3 C2 107.5(4) . . ?
C4 C3 H3 126.3 . . ?
C2 C3 H3 126.3 . . ?
C3 C4 N1 107.1(3) . . ?
C3 C4 C5 128.6(3) . . ?
N1 C4 C5 124.2(4) . . ?
O1 C5 C4 124.2(4) . . ?
O1 C5 C6 119.3(4) . . ?
C4 C5 C6 116.4(3) . . ?
O2 C6 C7 111.3(3) . . ?
O2 C6 C5 106.8(3) . . ?
C7 C6 C5 110.7(3) . . ?
O2 C6 H6 109.3 . . ?
C7 C6 H6 109.3 . . ?
C5 C6 H6 109.3 . . ?
O3 C7 C8 125.5(3) . . ?
O3 C7 C6 118.3(3) . . ?
C8 C7 C6 116.2(3) . . ?
N2 C8 C9 107.3(3) . . ?
N2 C8 C7 124.4(3) . . ?
C9 C8 C7 128.2(3) . . ?
C10 C9 C8 107.7(4) . . ?
C10 C9 H9 126.2 . . ?
C8 C9 H9 126.2 . . ?
C11 C10 C9 107.8(4) . . ?
C11 C10 H10 126.1 . . ?
C9 C10 H10 126.1 . . ?
N2 C11 C10 108.5(4) . . ?
N2 C11 H11 125.8 . . ?
C10 C11 H11 125.8 . . ?
N1 C12 H12A 109.5 . . ?
N1 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
N1 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N2 C13 H13A 109.5 . . ?
N2 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
N2 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
N3 C14 C15 109.4(4) . . ?
N3 C14 H14 125.3 . . ?
C15 C14 H14 125.3 . . ?
C14 C15 C16 107.5(3) . . ?
C14 C15 H15 126.3 . . ?
C16 C15 H15 126.3 . . ?
C17 C16 C15 107.4(3) . . ?
C17 C16 H16 126.3 . . ?
C15 C16 H16 126.3 . . ?
N3 C17 C16 107.2(3) . . ?
N3 C17 C18 124.4(4) . . ?
C16 C17 C18 128.4(4) . . ?
O4 C18 C17 124.8(4) . . ?
O4 C18 C19 119.1(4) . . ?
C17 C18 C19 116.1(4) . . ?
O5 C19 C20A 104.1(5) . . ?
O5 C19 C18 112.3(3) . . ?
C20A C19 C18 99.4(6) . . ?
O5 C19 C20B 108.5(4) . . ?
C18 C19 C20B 116.3(5) . . ?
O5 C19 H19 113.3 . . ?
C20A C19 H19 113.3 . . ?
C18 C19 H19 113.3 . . ?
N3 C25 H25A 109.5 . . ?
N3 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
N3 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 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
O6A C20A C21A C22A -178.0(12) . . . . ?
C19 C20A C21A C22A -1.2(19) . . . . ?
O6A C20A C21A N4A -4(2) . . . . ?
C19 C20A C21A N4A 172.5(6) . . . . ?
N4A C21A C22A C23A 0.6(14) . . . . ?
C20A C21A C22A C23A 174.9(12) . . . . ?
C21A C22A C23A C24A -0.5(15) . . . . ?
C22A C23A C24A N4A 0.2(17) . . . . ?
C23A C24A N4A C21A 0.2(15) . . . . ?
C23A C24A N4A C26A 177.2(9) . . . . ?
C22A C21A N4A C24A -0.6(13) . . . . ?
C20A C21A N4A C24A -175.6(12) . . . . ?
C22A C21A N4A C26A -177.4(9) . . . . ?
C20A C21A N4A C26A 7.5(15) . . . . ?
O6B C20B C21B C22B 165.9(11) . . . . ?
C19 C20B C21B C22B -16.5(16) . . . . ?
O6B C20B C21B N4B -12.2(16) . . . . ?
C19 C20B C21B N4B 165.3(8) . . . . ?
N4B C21B C22B C23B 1.3(12) . . . . ?
C20B C21B C22B C23B -177.1(9) . . . . ?
C21B C22B C23B C24B -0.9(11) . . . . ?
C22B C23B C24B N4B 0.1(10) . . . . ?
C23B C24B N4B C21B 0.7(11) . . . . ?
C23B C24B N4B C26B 178.1(8) . . . . ?
C22B C21B N4B C24B -1.2(12) . . . . ?
C20B C21B N4B C24B 177.3(9) . . . . ?
C22B C21B N4B C26B -178.6(9) . . . . ?
C20B C21B N4B C26B 0.0(16) . . . . ?
C4 N1 C1 C2 -0.8(4) . . . . ?
C12 N1 C1 C2 179.3(4) . . . . ?
N1 C1 C2 C3 0.8(5) . . . . ?
C1 C2 C3 C4 -0.5(5) . . . . ?
C2 C3 C4 N1 0.0(4) . . . . ?
C2 C3 C4 C5 -178.5(4) . . . . ?
C1 N1 C4 C3 0.5(4) . . . . ?
C12 N1 C4 C3 -179.6(4) . . . . ?
C1 N1 C4 C5 179.1(3) . . . . ?
C12 N1 C4 C5 -1.0(6) . . . . ?
C3 C4 C5 O1 165.1(4) . . . . ?
N1 C4 C5 O1 -13.2(6) . . . . ?
C3 C4 C5 C6 -18.6(5) . . . . ?
N1 C4 C5 C6 163.1(3) . . . . ?
O1 C5 C6 O2 88.9(4) . . . . ?
C4 C5 C6 O2 -87.5(4) . . . . ?
O1 C5 C6 C7 -32.4(5) . . . . ?
C4 C5 C6 C7 151.2(3) . . . . ?
O2 C6 C7 O3 -7.8(5) . . . . ?
C5 C6 C7 O3 110.8(4) . . . . ?
O2 C6 C7 C8 170.3(3) . . . . ?
C5 C6 C7 C8 -71.1(4) . . . . ?
C11 N2 C8 C9 -0.2(5) . . . . ?
C13 N2 C8 C9 179.8(5) . . . . ?
C11 N2 C8 C7 178.9(4) . . . . ?
C13 N2 C8 C7 -1.1(7) . . . . ?
O3 C7 C8 N2 -5.2(6) . . . . ?
C6 C7 C8 N2 176.8(4) . . . . ?
O3 C7 C8 C9 173.8(4) . . . . ?
C6 C7 C8 C9 -4.2(6) . . . . ?
N2 C8 C9 C10 0.2(4) . . . . ?
C7 C8 C9 C10 -178.8(4) . . . . ?
C8 C9 C10 C11 -0.2(5) . . . . ?
C8 N2 C11 C10 0.1(5) . . . . ?
C13 N2 C11 C10 -179.9(5) . . . . ?
C9 C10 C11 N2 0.0(5) . . . . ?
C17 N3 C14 C15 0.1(6) . . . . ?
C25 N3 C14 C15 178.6(6) . . . . ?
N3 C14 C15 C16 0.4(5) . . . . ?
C14 C15 C16 C17 -0.7(5) . . . . ?
C14 N3 C17 C16 -0.6(6) . . . . ?
C25 N3 C17 C16 -179.0(6) . . . . ?
C14 N3 C17 C18 177.1(5) . . . . ?
C25 N3 C17 C18 -1.3(9) . . . . ?
C15 C16 C17 N3 0.8(5) . . . . ?
C15 C16 C17 C18 -176.7(5) . . . . ?
N3 C17 C18 O4 -6.2(9) . . . . ?
C16 C17 C18 O4 170.9(6) . . . . ?
N3 C17 C18 C19 174.5(4) . . . . ?
C16 C17 C18 C19 -8.4(8) . . . . ?
O6A C20A C19 O5 78.4(11) . . . . ?
C21A C20A C19 O5 -98.6(9) . . . . ?
O6A C20A C19 C18 -37.5(11) . . . . ?
C21A C20A C19 C18 145.5(9) . . . . ?
O4 C18 C19 O5 -10.1(7) . . . . ?
C17 C18 C19 O5 169.4(4) . . . . ?
O4 C18 C19 C20A 99.4(7) . . . . ?
C17 C18 C19 C20A -81.1(6) . . . . ?
O4 C18 C19 C20B 115.8(7) . . . . ?
C17 C18 C19 C20B -64.8(6) . . . . ?
O6B C20B C19 O5 94.4(7) . . . . ?
C21B C20B C19 O5 -83.4(8) . . . . ?
O6B C20B C19 C18 -33.4(9) . . . . ?
C21B C20B C19 C18 148.8(7) . . . . ?

#==============================================================================
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_D
_geom_hbond_site_symmetry_H
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DA
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
O2 H2A O3 . . . 2.648(4) 0.840 2.180 115.0 no
O2 H2A O3 . . 2_665 2.872(4) 0.840 2.192 138.1 no
O5 H5 O4 . . . 2.666(5) 0.840 2.238 111.7 no
O5 H5 O4 . . 2_656 2.784(5) 0.840 2.069 142.7 no

#==============================================================================
# Additional structures and associated data_? identifiers
# should be added at this point if there is more than one 
# structure analysis in the CIF.





#==============================================================================
#     End of CIF
#==============================================================================
























































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































































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