# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_1a-AcOH
_database_code_depnum_ccdc_archive 'CCDC 2072840'
loop_
_audit_author_name
_audit_author_address
'Valentina Karnoukhova'
;A N Nesmeyanov Institute of Organoelement Compounds of Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2021-03-24 deposited with the CCDC.	2021-05-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H18 N4 O2, 2(C2 H4 O2)'
_chemical_formula_sum            'C22 H26 N4 O6'
_chemical_formula_weight         442.47
_chemical_absolute_configuration .

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   8.340(2)
_cell_length_b                   25.809(7)
_cell_length_c                   10.622(3)
_cell_angle_alpha                90
_cell_angle_beta                 94.689(7)
_cell_angle_gamma                90
_cell_volume                     2278.7(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    642
_cell_measurement_theta_min      3
_cell_measurement_theta_max      25

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.290
_exptl_crystal_F_000             936
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.095
_shelx_estimated_absorpt_T_min   0.976
_shelx_estimated_absorpt_T_max   0.983
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6556
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX DUO diffractometer'
_diffrn_detector_type            'Bruker APEX II CCD area detector'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            40191
_diffrn_reflns_av_unetI/netI     0.1348
_diffrn_reflns_av_R_equivalents  0.1111
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -36
_diffrn_reflns_limit_k_max       36
_diffrn_reflns_limit_l_min       -1
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.924
_diffrn_reflns_theta_max         30.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             13265
_reflns_number_gt                7289
_reflns_threshold_expression     I>2σ(I)
_reflns_Friedel_coverage         0.959
_reflns_Friedel_fraction_max     0.998
_reflns_Friedel_fraction_full    0.998

_reflns_special_details          
;
 _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.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015b)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_refine_special_details          'Refined as a 2-component twin.,Twin'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0557P)²+0.1302P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         13265
_refine_ls_number_parameters     602
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1506
_refine_ls_R_factor_gt           0.0765
_refine_ls_wR_factor_ref         0.1784
_refine_ls_wR_factor_gt          0.1482
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_restrained_S_all      1.022
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.5976(4) 0.44114(13) 0.4671(3) 0.0212(8) Uani 1 1 d . . . . .
O2 O 0.6399(5) 0.43732(14) 1.0204(3) 0.0212(8) Uani 1 1 d . . . . .
N1 N 0.7636(5) 0.46983(18) 0.6370(4) 0.0198(10) Uani 1 1 d . . . . .
H1N H 0.789(10) 0.504(3) 0.607(7) 0.07(3) Uiso 1 1 d . . . . .
N2 N 0.6911(5) 0.38732(16) 0.6287(4) 0.0195(10) Uani 1 1 d . . . . .
N3 N 0.7070(5) 0.38568(16) 0.8569(4) 0.0191(10) Uani 1 1 d . . . . .
N4 N 0.7938(5) 0.46625(17) 0.8639(4) 0.0200(10) Uani 1 1 d . . . . .
H4N H 0.801(10) 0.505(3) 0.896(7) 0.07(2) Uiso 1 1 d . . . . .
C1 C 0.8521(7) 0.44862(19) 0.7472(5) 0.0169(11) Uani 1 1 d . . . . .
C2 C 0.6765(6) 0.43379(19) 0.5681(5) 0.0159(10) Uani 1 1 d . . . . .
C3 C 0.7936(6) 0.38898(19) 0.7443(4) 0.0142(10) Uani 1 1 d . . . . .
C4 C 0.7075(6) 0.43066(19) 0.9228(5) 0.0165(10) Uani 1 1 d . . . . .
C5 C 1.0317(6) 0.4565(2) 0.7456(5) 0.0165(11) Uani 1 1 d . . . . .
C6 C 1.0997(7) 0.4607(2) 0.6309(6) 0.0275(13) Uani 1 1 d . . . . .
H6A H 1.033566 0.459674 0.553763 0.033 Uiso 1 1 calc R U . . .
C7 C 1.2663(8) 0.4663(3) 0.6300(7) 0.0379(17) Uani 1 1 d . . . . .
H7A H 1.313337 0.468969 0.551825 0.045 Uiso 1 1 calc R U . . .
C8 C 1.3629(8) 0.4681(2) 0.7417(7) 0.0380(17) Uani 1 1 d . . . . .
H8A H 1.475844 0.472739 0.741042 0.046 Uiso 1 1 calc R U . . .
C9 C 1.2938(9) 0.4631(3) 0.8535(7) 0.0421(18) Uani 1 1 d . . . . .
H9A H 1.360065 0.463709 0.930598 0.051 Uiso 1 1 calc R U . . .
C10 C 1.1299(7) 0.4571(2) 0.8565(6) 0.0272(13) Uani 1 1 d . . . . .
H10A H 1.084540 0.453377 0.935170 0.033 Uiso 1 1 calc R U . . .
C11 C 0.9307(6) 0.35054(19) 0.7455(4) 0.0150(10) Uani 1 1 d . . . . .
C12 C 0.9927(7) 0.3347(2) 0.6336(5) 0.0248(13) Uani 1 1 d . . . . .
H12A H 0.939278 0.344542 0.554866 0.030 Uiso 1 1 calc R U . . .
C13 C 1.1301(8) 0.3049(2) 0.6352(6) 0.0312(14) Uani 1 1 d . . . . .
H13A H 1.170465 0.294450 0.558046 0.037 Uiso 1 1 calc R U . . .
C14 C 1.2088(7) 0.2903(2) 0.7484(6) 0.0309(14) Uani 1 1 d . . . . .
H14A H 1.303899 0.270023 0.749489 0.037 Uiso 1 1 calc R U . . .
C15 C 1.1496(7) 0.3052(2) 0.8608(6) 0.0310(14) Uani 1 1 d . . . . .
H15A H 1.204245 0.295148 0.938978 0.037 Uiso 1 1 calc R U . . .
C16 C 1.0107(7) 0.3347(2) 0.8596(5) 0.0229(12) Uani 1 1 d . . . . .
H16A H 0.969560 0.344327 0.937055 0.028 Uiso 1 1 calc R U . . .
C17 C 0.5962(7) 0.34274(19) 0.5843(5) 0.0244(13) Uani 1 1 d . . . . .
H17A H 0.597711 0.339794 0.492429 0.037 Uiso 1 1 calc R U . . .
H17B H 0.485085 0.347098 0.606099 0.037 Uiso 1 1 calc R U . . .
H17C H 0.641846 0.311264 0.624495 0.037 Uiso 1 1 calc R U . . .
C18 C 0.6217(8) 0.3403(2) 0.8967(5) 0.0298(14) Uani 1 1 d . . . . .
H18A H 0.642780 0.335759 0.988147 0.045 Uiso 1 1 calc R U . . .
H18B H 0.658723 0.309650 0.853084 0.045 Uiso 1 1 calc R U . . .
H18C H 0.505950 0.344939 0.875749 0.045 Uiso 1 1 calc R U . . .
O1A O 0.7813(4) 0.56866(13) -0.0423(3) 0.0210(8) Uani 1 1 d . . . . .
O2A O 0.8341(5) 0.56164(14) 0.5126(3) 0.0228(8) Uani 1 1 d . . . . .
N1A N 0.6340(6) 0.53921(18) 0.1174(4) 0.0214(10) Uani 1 1 d . . . . .
H1NA H 0.628(6) 0.510(2) 0.095(5) 0.010(14) Uiso 1 1 d . . . . .
N2A N 0.7160(5) 0.62030(16) 0.1211(4) 0.0202(10) Uani 1 1 d . . . . .
N3A N 0.7462(5) 0.61644(16) 0.3511(4) 0.0201(10) Uani 1 1 d . . . . .
N4A N 0.6597(5) 0.53568(17) 0.3439(4) 0.0194(10) Uani 1 1 d . . . . .
H4NA H 0.623(8) 0.508(3) 0.379(6) 0.04(2) Uiso 1 1 d . . . . .
C1A C 0.5753(7) 0.55748(19) 0.2326(5) 0.0150(11) Uani 1 1 d . . . . .
C2A C 0.7171(6) 0.57478(19) 0.0566(5) 0.0181(11) Uani 1 1 d . . . . .
C3A C 0.6372(6) 0.6162(2) 0.2371(4) 0.0176(11) Uani 1 1 d . . . . .
C4A C 0.7533(6) 0.5700(2) 0.4110(5) 0.0186(11) Uani 1 1 d . . . . .
C5A C 0.3948(6) 0.5499(2) 0.2339(5) 0.0188(12) Uani 1 1 d . . . . .
C6A C 0.2999(7) 0.5480(2) 0.1203(6) 0.0267(14) Uani 1 1 d . . . . .
H6AA H 0.348425 0.550433 0.042707 0.032 Uiso 1 1 calc R U . . .
C7A C 0.1341(8) 0.5426(2) 0.1199(6) 0.0359(16) Uani 1 1 d . . . . .
H7AA H 0.069291 0.541857 0.042106 0.043 Uiso 1 1 calc R U . . .
C8A C 0.0642(8) 0.5383(3) 0.2320(7) 0.0404(17) Uani 1 1 d . . . . .
H8AA H -0.048776 0.533441 0.231612 0.048 Uiso 1 1 calc R U . . .
C9A C 0.3232(7) 0.5468(2) 0.3463(6) 0.0274(14) Uani 1 1 d . . . . .
H9AA H 0.387135 0.548489 0.424389 0.033 Uiso 1 1 calc R U . . .
C10A C 0.1571(8) 0.5411(3) 0.3449(7) 0.0366(16) Uani 1 1 d . . . . .
H10B H 0.107743 0.539160 0.422284 0.044 Uiso 1 1 calc R U . . .
C11A C 0.5016(7) 0.6552(2) 0.2426(4) 0.0185(11) Uani 1 1 d . . . . .
C12A C 0.4145(7) 0.6712(2) 0.1342(5) 0.0240(13) Uani 1 1 d . . . . .
H12B H 0.449421 0.661700 0.054437 0.029 Uiso 1 1 calc R U . . .
C13A C 0.2763(7) 0.7011(2) 0.1387(6) 0.0310(14) Uani 1 1 d . . . . .
H13B H 0.216199 0.711147 0.062766 0.037 Uiso 1 1 calc R U . . .
C14A C 0.2271(8) 0.7161(2) 0.2535(6) 0.0330(15) Uani 1 1 d . . . . .
H14B H 0.132778 0.736499 0.257132 0.040 Uiso 1 1 calc R U . . .
C15A C 0.3152(8) 0.7015(2) 0.3638(6) 0.0331(15) Uani 1 1 d . . . . .
H15B H 0.282194 0.711989 0.443382 0.040 Uiso 1 1 calc R U . . .
C16A C 0.4515(7) 0.6714(2) 0.3574(5) 0.0263(13) Uani 1 1 d . . . . .
H16B H 0.512165 0.661694 0.433277 0.032 Uiso 1 1 calc R U . . .
C17A C 0.8004(7) 0.6660(2) 0.0807(5) 0.0272(13) Uani 1 1 d . . . . .
H17D H 0.819778 0.662533 -0.008661 0.041 Uiso 1 1 calc R U . . .
H17E H 0.903513 0.669362 0.131362 0.041 Uiso 1 1 calc R U . . .
H17F H 0.734818 0.696883 0.092249 0.041 Uiso 1 1 calc R U . . .
C18A C 0.8457(8) 0.6597(2) 0.3956(5) 0.0288(14) Uani 1 1 d . . . . .
H18D H 0.877515 0.655410 0.485839 0.043 Uiso 1 1 calc R U . . .
H18E H 0.784980 0.692036 0.382247 0.043 Uiso 1 1 calc R U . . .
H18F H 0.942123 0.661033 0.348719 0.043 Uiso 1 1 calc R U . . .
O1S O 0.8333(8) 0.3018(3) 0.3379(5) 0.082(2) Uani 1 1 d . . . . .
O2S O 0.9605(8) 0.3132(3) 0.1658(5) 0.075(2) Uani 1 1 d . . . . .
H2S H 0.976754 0.278809 0.163197 0.090 Uiso 1 1 d R U . . .
O3S O 0.9821(7) 0.2115(3) 0.1587(5) 0.0687(18) Uani 1 1 d . . . . .
O4S O 0.8658(8) 0.1991(3) 0.3364(5) 0.087(2) Uani 1 1 d . . . . .
H4S H 0.858891 0.233832 0.329836 0.105 Uiso 1 1 d R U . . .
C1S C 0.8880(11) 0.3312(4) 0.2581(6) 0.069(3) Uani 1 1 d . . . . .
C2S C 0.8777(13) 0.3892(4) 0.2657(7) 0.085(4) Uani 1 1 d . . . . .
H2SB H 0.850835 0.403434 0.181054 0.127 Uiso 1 1 calc R U . . .
H2SC H 0.981490 0.403164 0.300097 0.127 Uiso 1 1 calc R U . . .
H2SD H 0.794072 0.398911 0.320956 0.127 Uiso 1 1 calc R U . . .
C3S C 0.9329(10) 0.1819(4) 0.2399(6) 0.062(3) Uani 1 1 d . . . . .
C4S C 0.9475(11) 0.1258(4) 0.2332(7) 0.071(3) Uani 1 1 d . . . . .
H4SB H 1.012024 0.116509 0.163495 0.106 Uiso 1 1 calc R U . . .
H4SC H 0.840201 0.110344 0.218761 0.106 Uiso 1 1 calc R U . . .
H4SD H 1.000036 0.112715 0.312813 0.106 Uiso 1 1 calc R U . . .
O1SA O 0.5483(8) 0.7882(3) 0.8500(6) 0.082(2) Uani 1 1 d . . . . .
O2SA O 0.6731(8) 0.7948(3) 0.6741(5) 0.077(2) Uani 1 1 d . . . . .
H2SA H 0.659200 0.760263 0.673635 0.092 Uiso 1 1 d R U . . .
O3SA O 0.6404(8) 0.6929(3) 0.6602(5) 0.0729(18) Uani 1 1 d . . . . .
O4SA O 0.4953(8) 0.6869(3) 0.8246(5) 0.076(2) Uani 1 1 d . . . . .
H4SA H 0.516212 0.721089 0.824421 0.091 Uiso 1 1 d R U . . .
C1SA C 0.6116(11) 0.8145(4) 0.7726(7) 0.064(3) Uani 1 1 d . . . . .
C2SA C 0.6252(12) 0.8714(4) 0.7833(8) 0.074(3) Uani 1 1 d . . . . .
H2SE H 0.558807 0.883721 0.849129 0.111 Uiso 1 1 calc R U . . .
H2SF H 0.588084 0.887318 0.702354 0.111 Uiso 1 1 calc R U . . .
H2SG H 0.737742 0.880881 0.805440 0.111 Uiso 1 1 calc R U . . .
C3SA C 0.5609(11) 0.6656(4) 0.7288(7) 0.061(2) Uani 1 1 d . . . . .
C4SA C 0.5357(11) 0.6109(4) 0.7104(7) 0.069(3) Uani 1 1 d . . . . .
H4SE H 0.624618 0.596289 0.666874 0.103 Uiso 1 1 calc R U . . .
H4SF H 0.434154 0.605149 0.659148 0.103 Uiso 1 1 calc R U . . .
H4SG H 0.531320 0.593900 0.792549 0.103 Uiso 1 1 calc R U . . .


_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 C2 1.227(6) . ?
O2 C4 1.232(6) . ?
N1 C2 1.357(7) . ?
N1 C1 1.439(6) . ?
N1 H1N 0.97(8) . ?
N2 C2 1.362(6) . ?
N2 C3 1.438(6) . ?
N2 C17 1.453(6) . ?
N3 C4 1.355(6) . ?
N3 C3 1.450(6) . ?
N3 C18 1.450(7) . ?
N4 C4 1.351(7) . ?
N4 C1 1.442(7) . ?
N4 H4N 1.06(8) . ?
C1 C5 1.513(8) . ?
C1 C3 1.614(7) . ?
C3 C11 1.513(7) . ?
C5 C10 1.379(7) . ?
C5 C6 1.389(8) . ?
C6 C7 1.397(9) . ?
C6 H6A 0.9500 . ?
C7 C8 1.380(9) . ?
C7 H7A 0.9500 . ?
C8 C9 1.367(10) . ?
C8 H8A 0.9500 . ?
C9 C10 1.378(9) . ?
C9 H9A 0.9500 . ?
C10 H10A 0.9500 . ?
C11 C16 1.396(7) . ?
C11 C12 1.396(7) . ?
C12 C13 1.378(8) . ?
C12 H12A 0.9500 . ?
C13 C14 1.374(9) . ?
C13 H13A 0.9500 . ?
C14 C15 1.383(8) . ?
C14 H14A 0.9500 . ?
C15 C16 1.386(8) . ?
C15 H15A 0.9500 . ?
C16 H16A 0.9500 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
O1A C2A 1.228(6) . ?
O2A C4A 1.244(6) . ?
N1A C2A 1.347(7) . ?
N1A C1A 1.434(7) . ?
N1A H1NA 0.80(5) . ?
N2A C2A 1.360(6) . ?
N2A C3A 1.447(6) . ?
N2A C17A 1.457(7) . ?
N3A C4A 1.356(6) . ?
N3A C18A 1.448(7) . ?
N3A C3A 1.453(6) . ?
N4A C4A 1.346(7) . ?
N4A C1A 1.440(6) . ?
N4A H4NA 0.87(7) . ?
C1A C5A 1.518(8) . ?
C1A C3A 1.600(7) . ?
C3A C11A 1.519(7) . ?
C5A C9A 1.380(8) . ?
C5A C6A 1.388(7) . ?
C6A C7A 1.389(9) . ?
C6A H6AA 0.9500 . ?
C7A C8A 1.373(9) . ?
C7A H7AA 0.9500 . ?
C8A C10A 1.376(9) . ?
C8A H8AA 0.9500 . ?
C9A C10A 1.392(9) . ?
C9A H9AA 0.9500 . ?
C10A H10B 0.9500 . ?
C11A C12A 1.374(7) . ?
C11A C16A 1.385(7) . ?
C12A C13A 1.392(8) . ?
C12A H12B 0.9500 . ?
C13A C14A 1.373(9) . ?
C13A H13B 0.9500 . ?
C14A C15A 1.384(9) . ?
C14A H14B 0.9500 . ?
C15A C16A 1.383(8) . ?
C15A H15B 0.9500 . ?
C16A H16B 0.9500 . ?
C17A H17D 0.9800 . ?
C17A H17E 0.9800 . ?
C17A H17F 0.9800 . ?
C18A H18D 0.9800 . ?
C18A H18E 0.9800 . ?
C18A H18F 0.9800 . ?
O1S C1S 1.251(11) . ?
O2S C1S 1.279(9) . ?
O2S H2S 0.9000 . ?
O3S C3S 1.246(11) . ?
O4S C3S 1.286(9) . ?
O4S H4S 0.9000 . ?
C1S C2S 1.502(14) . ?
C2S H2SB 0.9800 . ?
C2S H2SC 0.9800 . ?
C2S H2SD 0.9800 . ?
C3S C4S 1.456(14) . ?
C4S H4SB 0.9800 . ?
C4S H4SC 0.9800 . ?
C4S H4SD 0.9800 . ?
O1SA C1SA 1.219(10) . ?
O2SA C1SA 1.305(10) . ?
O2SA H2SA 0.8999 . ?
O3SA C3SA 1.243(11) . ?
O4SA C3SA 1.314(9) . ?
O4SA H4SA 0.9002 . ?
C1SA C2SA 1.477(14) . ?
C2SA H2SE 0.9800 . ?
C2SA H2SF 0.9800 . ?
C2SA H2SG 0.9800 . ?
C3SA C4SA 1.439(13) . ?
C4SA H4SE 0.9800 . ?
C4SA H4SF 0.9800 . ?
C4SA H4SG 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
C2 N1 C1 113.2(4) . . ?
C2 N1 H1N 124(5) . . ?
C1 N1 H1N 120(5) . . ?
C2 N2 C3 113.7(4) . . ?
C2 N2 C17 121.2(4) . . ?
C3 N2 C17 124.8(4) . . ?
C4 N3 C3 113.3(4) . . ?
C4 N3 C18 121.5(4) . . ?
C3 N3 C18 125.2(4) . . ?
C4 N4 C1 114.4(4) . . ?
C4 N4 H4N 121(4) . . ?
C1 N4 H4N 124(4) . . ?
N1 C1 N4 113.1(4) . . ?
N1 C1 C5 112.5(5) . . ?
N4 C1 C5 111.8(4) . . ?
N1 C1 C3 102.3(4) . . ?
N4 C1 C3 101.2(4) . . ?
C5 C1 C3 115.3(4) . . ?
O1 C2 N1 126.2(5) . . ?
O1 C2 N2 124.8(5) . . ?
N1 C2 N2 109.0(4) . . ?
N2 C3 N3 113.7(4) . . ?
N2 C3 C11 112.5(4) . . ?
N3 C3 C11 112.5(4) . . ?
N2 C3 C1 101.7(4) . . ?
N3 C3 C1 102.2(4) . . ?
C11 C3 C1 113.4(4) . . ?
O2 C4 N4 126.3(5) . . ?
O2 C4 N3 124.8(5) . . ?
N4 C4 N3 108.8(4) . . ?
C10 C5 C6 119.5(5) . . ?
C10 C5 C1 120.8(5) . . ?
C6 C5 C1 119.7(5) . . ?
C5 C6 C7 119.4(6) . . ?
C5 C6 H6A 120.3 . . ?
C7 C6 H6A 120.3 . . ?
C8 C7 C6 120.6(7) . . ?
C8 C7 H7A 119.7 . . ?
C6 C7 H7A 119.7 . . ?
C9 C8 C7 119.0(7) . . ?
C9 C8 H8A 120.5 . . ?
C7 C8 H8A 120.5 . . ?
C8 C9 C10 121.3(7) . . ?
C8 C9 H9A 119.3 . . ?
C10 C9 H9A 119.3 . . ?
C9 C10 C5 120.2(6) . . ?
C9 C10 H10A 119.9 . . ?
C5 C10 H10A 119.9 . . ?
C16 C11 C12 118.0(5) . . ?
C16 C11 C3 120.4(4) . . ?
C12 C11 C3 121.2(4) . . ?
C13 C12 C11 121.3(5) . . ?
C13 C12 H12A 119.4 . . ?
C11 C12 H12A 119.4 . . ?
C14 C13 C12 120.0(6) . . ?
C14 C13 H13A 120.0 . . ?
C12 C13 H13A 120.0 . . ?
C13 C14 C15 120.1(6) . . ?
C13 C14 H14A 120.0 . . ?
C15 C14 H14A 120.0 . . ?
C14 C15 C16 120.1(5) . . ?
C14 C15 H15A 120.0 . . ?
C16 C15 H15A 120.0 . . ?
C15 C16 C11 120.6(5) . . ?
C15 C16 H16A 119.7 . . ?
C11 C16 H16A 119.7 . . ?
N2 C17 H17A 109.5 . . ?
N2 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
N2 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N3 C18 H18A 109.5 . . ?
N3 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N3 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C2A N1A C1A 114.2(4) . . ?
C2A N1A H1NA 122(4) . . ?
C1A N1A H1NA 124(4) . . ?
C2A N2A C3A 112.8(4) . . ?
C2A N2A C17A 121.8(4) . . ?
C3A N2A C17A 125.1(4) . . ?
C4A N3A C18A 121.8(4) . . ?
C4A N3A C3A 112.8(4) . . ?
C18A N3A C3A 125.3(4) . . ?
C4A N4A C1A 113.6(4) . . ?
C4A N4A H4NA 122(4) . . ?
C1A N4A H4NA 120(4) . . ?
N1A C1A N4A 113.2(4) . . ?
N1A C1A C5A 111.9(4) . . ?
N4A C1A C5A 111.2(4) . . ?
N1A C1A C3A 101.8(4) . . ?
N4A C1A C3A 102.1(4) . . ?
C5A C1A C3A 116.0(4) . . ?
O1A C2A N1A 126.9(5) . . ?
O1A C2A N2A 124.3(5) . . ?
N1A C2A N2A 108.8(4) . . ?
N2A C3A N3A 114.3(4) . . ?
N2A C3A C11A 112.0(4) . . ?
N3A C3A C11A 112.4(4) . . ?
N2A C3A C1A 102.3(4) . . ?
N3A C3A C1A 102.0(4) . . ?
C11A C3A C1A 113.0(4) . . ?
O2A C4A N4A 126.5(5) . . ?
O2A C4A N3A 124.1(5) . . ?
N4A C4A N3A 109.4(4) . . ?
C9A C5A C6A 119.5(5) . . ?
C9A C5A C1A 121.0(5) . . ?
C6A C5A C1A 119.5(5) . . ?
C5A C6A C7A 120.2(6) . . ?
C5A C6A H6AA 119.9 . . ?
C7A C6A H6AA 119.9 . . ?
C8A C7A C6A 119.9(6) . . ?
C8A C7A H7AA 120.0 . . ?
C6A C7A H7AA 120.0 . . ?
C7A C8A C10A 120.2(6) . . ?
C7A C8A H8AA 119.9 . . ?
C10A C8A H8AA 119.9 . . ?
C5A C9A C10A 119.9(6) . . ?
C5A C9A H9AA 120.1 . . ?
C10A C9A H9AA 120.1 . . ?
C8A C10A C9A 120.3(6) . . ?
C8A C10A H10B 119.9 . . ?
C9A C10A H10B 119.9 . . ?
C12A C11A C16A 118.0(5) . . ?
C12A C11A C3A 120.8(5) . . ?
C16A C11A C3A 120.8(4) . . ?
C11A C12A C13A 121.4(5) . . ?
C11A C12A H12B 119.3 . . ?
C13A C12A H12B 119.3 . . ?
C14A C13A C12A 119.7(6) . . ?
C14A C13A H13B 120.2 . . ?
C12A C13A H13B 120.2 . . ?
C13A C14A C15A 119.9(6) . . ?
C13A C14A H14B 120.0 . . ?
C15A C14A H14B 120.0 . . ?
C16A C15A C14A 119.6(6) . . ?
C16A C15A H15B 120.2 . . ?
C14A C15A H15B 120.2 . . ?
C15A C16A C11A 121.4(5) . . ?
C15A C16A H16B 119.3 . . ?
C11A C16A H16B 119.3 . . ?
N2A C17A H17D 109.5 . . ?
N2A C17A H17E 109.5 . . ?
H17D C17A H17E 109.5 . . ?
N2A C17A H17F 109.5 . . ?
H17D C17A H17F 109.5 . . ?
H17E C17A H17F 109.5 . . ?
N3A C18A H18D 109.5 . . ?
N3A C18A H18E 109.5 . . ?
H18D C18A H18E 109.5 . . ?
N3A C18A H18F 109.5 . . ?
H18D C18A H18F 109.5 . . ?
H18E C18A H18F 109.5 . . ?
C1S O2S H2S 117.6 . . ?
C3S O4S H4S 108.2 . . ?
O1S C1S O2S 121.4(10) . . ?
O1S C1S C2S 122.8(8) . . ?
O2S C1S C2S 115.8(9) . . ?
C1S C2S H2SB 109.5 . . ?
C1S C2S H2SC 109.5 . . ?
H2SB C2S H2SC 109.5 . . ?
C1S C2S H2SD 109.5 . . ?
H2SB C2S H2SD 109.5 . . ?
H2SC C2S H2SD 109.5 . . ?
O3S C3S O4S 122.0(10) . . ?
O3S C3S C4S 122.8(7) . . ?
O4S C3S C4S 115.2(9) . . ?
C3S C4S H4SB 109.5 . . ?
C3S C4S H4SC 109.5 . . ?
H4SB C4S H4SC 109.5 . . ?
C3S C4S H4SD 109.5 . . ?
H4SB C4S H4SD 109.5 . . ?
H4SC C4S H4SD 109.5 . . ?
C1SA O2SA H2SA 109.3 . . ?
C3SA O4SA H4SA 108.4 . . ?
O1SA C1SA O2SA 123.1(10) . . ?
O1SA C1SA C2SA 122.4(8) . . ?
O2SA C1SA C2SA 114.5(9) . . ?
C1SA C2SA H2SE 109.5 . . ?
C1SA C2SA H2SF 109.5 . . ?
H2SE C2SA H2SF 109.5 . . ?
C1SA C2SA H2SG 109.5 . . ?
H2SE C2SA H2SG 109.5 . . ?
H2SF C2SA H2SG 109.5 . . ?
O3SA C3SA O4SA 119.6(9) . . ?
O3SA C3SA C4SA 123.7(8) . . ?
O4SA C3SA C4SA 116.7(9) . . ?
C3SA C4SA H4SE 109.5 . . ?
C3SA C4SA H4SF 109.5 . . ?
H4SE C4SA H4SF 109.5 . . ?
C3SA C4SA H4SG 109.5 . . ?
H4SE C4SA H4SG 109.5 . . ?
H4SF C4SA H4SG 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
C2 N1 C1 N4 -112.4(5) . . . . ?
C2 N1 C1 C5 119.9(5) . . . . ?
C2 N1 C1 C3 -4.4(6) . . . . ?
C4 N4 C1 N1 104.9(5) . . . . ?
C4 N4 C1 C5 -127.0(5) . . . . ?
C4 N4 C1 C3 -3.8(5) . . . . ?
C1 N1 C2 O1 -176.0(5) . . . . ?
C1 N1 C2 N2 3.6(6) . . . . ?
C3 N2 C2 O1 178.7(5) . . . . ?
C17 N2 C2 O1 -7.6(8) . . . . ?
C3 N2 C2 N1 -0.9(6) . . . . ?
C17 N2 C2 N1 172.9(5) . . . . ?
C2 N2 C3 N3 107.2(5) . . . . ?
C17 N2 C3 N3 -66.2(6) . . . . ?
C2 N2 C3 C11 -123.4(5) . . . . ?
C17 N2 C3 C11 63.1(6) . . . . ?
C2 N2 C3 C1 -1.8(6) . . . . ?
C17 N2 C3 C1 -175.2(5) . . . . ?
C4 N3 C3 N2 -109.8(5) . . . . ?
C18 N3 C3 N2 68.1(6) . . . . ?
C4 N3 C3 C11 120.9(5) . . . . ?
C18 N3 C3 C11 -61.2(6) . . . . ?
C4 N3 C3 C1 -1.1(5) . . . . ?
C18 N3 C3 C1 176.8(5) . . . . ?
N1 C1 C3 N2 3.5(5) . . . . ?
N4 C1 C3 N2 120.4(4) . . . . ?
C5 C1 C3 N2 -118.9(5) . . . . ?
N1 C1 C3 N3 -114.2(4) . . . . ?
N4 C1 C3 N3 2.7(5) . . . . ?
C5 C1 C3 N3 123.4(5) . . . . ?
N1 C1 C3 C11 124.5(4) . . . . ?
N4 C1 C3 C11 -118.6(4) . . . . ?
C5 C1 C3 C11 2.2(6) . . . . ?
C1 N4 C4 O2 -176.7(5) . . . . ?
C1 N4 C4 N3 3.4(6) . . . . ?
C3 N3 C4 O2 178.9(4) . . . . ?
C18 N3 C4 O2 0.9(8) . . . . ?
C3 N3 C4 N4 -1.2(6) . . . . ?
C18 N3 C4 N4 -179.2(5) . . . . ?
N1 C1 C5 C10 155.8(5) . . . . ?
N4 C1 C5 C10 27.3(7) . . . . ?
C3 C1 C5 C10 -87.5(6) . . . . ?
N1 C1 C5 C6 -27.5(7) . . . . ?
N4 C1 C5 C6 -155.9(5) . . . . ?
C3 C1 C5 C6 89.3(6) . . . . ?
C10 C5 C6 C7 -1.2(9) . . . . ?
C1 C5 C6 C7 -178.0(5) . . . . ?
C5 C6 C7 C8 -0.4(10) . . . . ?
C6 C7 C8 C9 1.5(10) . . . . ?
C7 C8 C9 C10 -1.0(11) . . . . ?
C8 C9 C10 C5 -0.6(10) . . . . ?
C6 C5 C10 C9 1.7(9) . . . . ?
C1 C5 C10 C9 178.4(5) . . . . ?
N2 C3 C11 C16 -159.7(5) . . . . ?
N3 C3 C11 C16 -29.8(7) . . . . ?
C1 C3 C11 C16 85.5(6) . . . . ?
N2 C3 C11 C12 27.8(7) . . . . ?
N3 C3 C11 C12 157.8(5) . . . . ?
C1 C3 C11 C12 -86.9(6) . . . . ?
C16 C11 C12 C13 -0.9(8) . . . . ?
C3 C11 C12 C13 171.7(5) . . . . ?
C11 C12 C13 C14 0.0(9) . . . . ?
C12 C13 C14 C15 0.4(9) . . . . ?
C13 C14 C15 C16 0.1(9) . . . . ?
C14 C15 C16 C11 -1.1(9) . . . . ?
C12 C11 C16 C15 1.5(8) . . . . ?
C3 C11 C16 C15 -171.2(5) . . . . ?
C2A N1A C1A N4A -108.2(5) . . . . ?
C2A N1A C1A C5A 125.2(5) . . . . ?
C2A N1A C1A C3A 0.6(6) . . . . ?
C4A N4A C1A N1A 109.9(5) . . . . ?
C4A N4A C1A C5A -123.2(5) . . . . ?
C4A N4A C1A C3A 1.2(6) . . . . ?
C1A N1A C2A O1A 178.9(5) . . . . ?
C1A N1A C2A N2A -2.6(6) . . . . ?
C3A N2A C2A O1A -177.8(5) . . . . ?
C17A N2A C2A O1A -3.4(8) . . . . ?
C3A N2A C2A N1A 3.7(6) . . . . ?
C17A N2A C2A N1A 178.1(5) . . . . ?
C2A N2A C3A N3A 106.2(5) . . . . ?
C17A N2A C3A N3A -67.9(7) . . . . ?
C2A N2A C3A C11A -124.4(5) . . . . ?
C17A N2A C3A C11A 61.4(7) . . . . ?
C2A N2A C3A C1A -3.2(6) . . . . ?
C17A N2A C3A C1A -177.3(5) . . . . ?
C4A N3A C3A N2A -110.9(5) . . . . ?
C18A N3A C3A N2A 65.7(7) . . . . ?
C4A N3A C3A C11A 119.9(5) . . . . ?
C18A N3A C3A C11A -63.5(7) . . . . ?
C4A N3A C3A C1A -1.4(6) . . . . ?
C18A N3A C3A C1A 175.2(5) . . . . ?
N1A C1A C3A N2A 1.4(5) . . . . ?
N4A C1A C3A N2A 118.6(4) . . . . ?
C5A C1A C3A N2A -120.3(5) . . . . ?
N1A C1A C3A N3A -117.1(4) . . . . ?
N4A C1A C3A N3A 0.1(5) . . . . ?
C5A C1A C3A N3A 121.2(5) . . . . ?
N1A C1A C3A C11A 122.0(4) . . . . ?
N4A C1A C3A C11A -120.8(4) . . . . ?
C5A C1A C3A C11A 0.2(6) . . . . ?
C1A N4A C4A O2A 177.4(5) . . . . ?
C1A N4A C4A N3A -2.1(6) . . . . ?
C18A N3A C4A O2A 6.0(8) . . . . ?
C3A N3A C4A O2A -177.3(5) . . . . ?
C18A N3A C4A N4A -174.5(5) . . . . ?
C3A N3A C4A N4A 2.2(6) . . . . ?
N1A C1A C5A C9A 156.3(5) . . . . ?
N4A C1A C5A C9A 28.7(7) . . . . ?
C3A C1A C5A C9A -87.4(6) . . . . ?
N1A C1A C5A C6A -26.0(7) . . . . ?
N4A C1A C5A C6A -153.7(5) . . . . ?
C3A C1A C5A C6A 90.2(6) . . . . ?
C9A C5A C6A C7A -0.5(9) . . . . ?
C1A C5A C6A C7A -178.2(5) . . . . ?
C5A C6A C7A C8A -1.0(9) . . . . ?
C6A C7A C8A C10A 2.1(10) . . . . ?
C6A C5A C9A C10A 0.8(9) . . . . ?
C1A C5A C9A C10A 178.4(5) . . . . ?
C7A C8A C10A C9A -1.9(11) . . . . ?
C5A C9A C10A C8A 0.4(10) . . . . ?
N2A C3A C11A C12A 31.2(7) . . . . ?
N3A C3A C11A C12A 161.5(5) . . . . ?
C1A C3A C11A C12A -83.7(6) . . . . ?
N2A C3A C11A C16A -155.7(5) . . . . ?
N3A C3A C11A C16A -25.4(7) . . . . ?
C1A C3A C11A C16A 89.4(6) . . . . ?
C16A C11A C12A C13A -2.5(8) . . . . ?
C3A C11A C12A C13A 170.8(5) . . . . ?
C11A C12A C13A C14A 1.5(9) . . . . ?
C12A C13A C14A C15A 0.1(9) . . . . ?
C13A C14A C15A C16A -0.6(9) . . . . ?
C14A C15A C16A C11A -0.5(9) . . . . ?
C12A C11A C16A C15A 2.0(8) . . . . ?
C3A C11A C16A C15A -171.3(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
N1 H1N O2A 0.97(8) 1.85(8) 2.799(6) 167(7) .
N4 H4N O1A 1.06(8) 1.78(8) 2.830(6) 171(7) 1_556
N1A H1NA O2 0.80(5) 2.03(5) 2.826(6) 172(5) 1_554
N4A H4NA O1 0.87(7) 1.98(7) 2.836(6) 165(6) .
O2S H2S O3S 0.90 1.74 2.635(10) 172.8 .
O4S H4S O1S 0.90 1.77 2.665(11) 171.9 .
O2SA H2SA O3SA 0.90 1.75 2.648(10) 174.9 .
O4SA H4SA O1SA 0.90 1.77 2.662(10) 170.5 .

_refine_diff_density_max         0.362
_refine_diff_density_min         -0.388
_refine_diff_density_rms         0.077



####################################################################### 
# 
# 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_1a-HCOOH
_database_code_depnum_ccdc_archive 'CCDC 2072844'
loop_
_audit_author_name
_audit_author_address
'Valentina Karnoukhova'
;A N Nesmeyanov Institute of Organoelement Compounds of Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2021-03-24 deposited with the CCDC.	2021-05-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H18 N4 O2, C H2 O2'
_chemical_formula_sum            'C19 H20 N4 O4'
_chemical_formula_weight         368.39

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.2955(10)
_cell_length_b                   9.6189(10)
_cell_length_c                   11.1769(12)
_cell_angle_alpha                68.975(2)
_cell_angle_beta                 70.514(2)
_cell_angle_gamma                82.886(2)
_cell_volume                     879.38(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    382
_cell_measurement_theta_min      3
_cell_measurement_theta_max      25

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.391
_exptl_crystal_F_000             388
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.390
_exptl_crystal_size_mid          0.350
_exptl_crystal_size_min          0.290
_exptl_absorpt_coefficient_mu    0.100
_shelx_estimated_absorpt_T_min   0.962
_shelx_estimated_absorpt_T_max   0.972
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6732
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX DUO diffractometer'
_diffrn_detector_type            'Bruker APEX II CCD area detector'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11709
_diffrn_reflns_av_unetI/netI     0.0306
_diffrn_reflns_av_R_equivalents  0.0225
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.055
_diffrn_reflns_theta_max         30.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5116
_reflns_number_gt                4354
_reflns_threshold_expression     I>2σ(I)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015b)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0548P)²+0.2519P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5116
_refine_ls_number_parameters     258
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0489
_refine_ls_R_factor_gt           0.0410
_refine_ls_wR_factor_ref         0.1090
_refine_ls_wR_factor_gt          0.1033
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 1.12896(9) 0.09543(9) 0.69930(8) 0.02070(18) Uani 1 1 d . . . . .
O2 O 0.56460(9) 0.03898(8) 1.11744(8) 0.01642(16) Uani 1 1 d . . . . .
N1 N 0.89765(10) 0.21175(10) 0.68899(9) 0.01506(18) Uani 1 1 d . . . . .
H1N H 0.8844(19) 0.1666(18) 0.6381(17) 0.029(4) Uiso 1 1 d . . . . .
N2 N 0.98743(10) 0.21142(10) 0.84952(9) 0.01497(18) Uani 1 1 d . . . . .
N3 N 0.73970(10) 0.22997(10) 1.00795(9) 0.01386(17) Uani 1 1 d . . . . .
N4 N 0.67724(10) 0.12260(10) 0.88675(9) 0.01407(17) Uani 1 1 d . . . . .
H4N H 0.6148(19) 0.0789(18) 0.8719(17) 0.029(4) Uiso 1 1 d . . . . .
C1 C 0.76690(11) 0.25167(11) 0.78430(10) 0.01267(19) Uani 1 1 d . . . . .
C2 C 1.01590(12) 0.16449(11) 0.74222(11) 0.0152(2) Uani 1 1 d . . . . .
C3 C 0.84453(11) 0.29455(11) 0.87332(10) 0.01257(18) Uani 1 1 d . . . . .
C4 C 0.65261(11) 0.12338(11) 1.01286(10) 0.01354(19) Uani 1 1 d . . . . .
C5 C 0.66988(12) 0.37239(11) 0.71699(10) 0.01333(19) Uani 1 1 d . . . . .
C6 C 0.73920(12) 0.48734(12) 0.59850(11) 0.0167(2) Uani 1 1 d . . . . .
H6A H 0.846610 0.486230 0.557529 0.020 Uiso 1 1 calc R U . . .
C7 C 0.65256(14) 0.60306(12) 0.54018(12) 0.0196(2) Uani 1 1 d . . . . .
H7A H 0.700881 0.681555 0.460221 0.024 Uiso 1 1 calc R U . . .
C8 C 0.49536(14) 0.60451(13) 0.59833(12) 0.0208(2) Uani 1 1 d . . . . .
H8A H 0.435754 0.683396 0.558057 0.025 Uiso 1 1 calc R U . . .
C9 C 0.42606(13) 0.49046(13) 0.71520(12) 0.0202(2) Uani 1 1 d . . . . .
H9A H 0.318424 0.491021 0.754996 0.024 Uiso 1 1 calc R U . . .
C10 C 0.51247(12) 0.37507(12) 0.77493(11) 0.0167(2) Uani 1 1 d . . . . .
H10A H 0.463813 0.297666 0.855690 0.020 Uiso 1 1 calc R U . . .
C11 C 0.86883(12) 0.45972(11) 0.83483(10) 0.01348(19) Uani 1 1 d . . . . .
C12 C 1.00308(12) 0.52585(12) 0.73823(11) 0.0166(2) Uani 1 1 d . . . . .
H12A H 1.082267 0.465853 0.702005 0.020 Uiso 1 1 calc R U . . .
C13 C 1.02243(14) 0.67924(13) 0.69416(12) 0.0211(2) Uani 1 1 d . . . . .
H13A H 1.114490 0.723521 0.628024 0.025 Uiso 1 1 calc R U . . .
C14 C 0.90778(15) 0.76716(13) 0.74657(13) 0.0240(2) Uani 1 1 d . . . . .
H14A H 0.921216 0.871786 0.716955 0.029 Uiso 1 1 calc R U . . .
C15 C 0.77311(15) 0.70240(13) 0.84245(13) 0.0228(2) Uani 1 1 d . . . . .
H15A H 0.693970 0.762974 0.877887 0.027 Uiso 1 1 calc R U . . .
C16 C 0.75341(13) 0.54910(12) 0.88696(11) 0.0176(2) Uani 1 1 d . . . . .
H16A H 0.661127 0.505235 0.953003 0.021 Uiso 1 1 calc R U . . .
C17 C 1.09564(13) 0.19278(13) 0.92193(12) 0.0194(2) Uani 1 1 d . . . . .
H17A H 1.194215 0.160463 0.872007 0.029 Uiso 1 1 calc R U . . .
H17B H 1.057834 0.117511 1.011662 0.029 Uiso 1 1 calc R U . . .
H17C H 1.108158 0.287732 0.931162 0.029 Uiso 1 1 calc R U . . .
C18 C 0.75874(13) 0.23978(12) 1.12881(11) 0.0178(2) Uani 1 1 d . . . . .
H18A H 0.660835 0.265742 1.185042 0.027 Uiso 1 1 calc R U . . .
H18B H 0.834053 0.316638 1.103020 0.027 Uiso 1 1 calc R U . . .
H18C H 0.794156 0.143549 1.179715 0.027 Uiso 1 1 calc R U . . .
O1S O 0.27821(10) -0.07977(10) 0.40638(9) 0.02588(19) Uani 1 1 d . . . . .
O2S O 0.47000(11) 0.06754(11) 0.36077(9) 0.0279(2) Uani 1 1 d . . . . .
H2S H 0.503(2) 0.047(2) 0.285(2) 0.045(5) Uiso 1 1 d . . . . .
C1S C 0.33844(13) 0.00181(13) 0.43520(12) 0.0206(2) Uani 1 1 d . . . . .
H1S H 0.287423 0.019947 0.517354 0.025 Uiso 1 1 calc R U . . .


_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 C2 1.2229(13) . ?
O2 C4 1.2411(12) . ?
N1 C2 1.3737(14) . ?
N1 C1 1.4400(13) . ?
N1 H1N 0.874(17) . ?
N2 C2 1.3635(14) . ?
N2 C17 1.4468(14) . ?
N2 C3 1.4588(13) . ?
N3 C4 1.3583(13) . ?
N3 C3 1.4494(13) . ?
N3 C18 1.4561(14) . ?
N4 C4 1.3531(14) . ?
N4 C1 1.4651(13) . ?
N4 H4N 0.846(17) . ?
C1 C5 1.5146(14) . ?
C1 C3 1.5900(14) . ?
C3 C11 1.5145(14) . ?
C5 C10 1.3897(15) . ?
C5 C6 1.3957(14) . ?
C6 C7 1.3857(15) . ?
C6 H6A 0.9500 . ?
C7 C8 1.3877(17) . ?
C7 H7A 0.9500 . ?
C8 C9 1.3821(17) . ?
C8 H8A 0.9500 . ?
C9 C10 1.3886(15) . ?
C9 H9A 0.9500 . ?
C10 H10A 0.9500 . ?
C11 C12 1.3902(14) . ?
C11 C16 1.3942(15) . ?
C12 C13 1.3917(15) . ?
C12 H12A 0.9500 . ?
C13 C14 1.3819(18) . ?
C13 H13A 0.9500 . ?
C14 C15 1.3866(18) . ?
C14 H14A 0.9500 . ?
C15 C16 1.3911(15) . ?
C15 H15A 0.9500 . ?
C16 H16A 0.9500 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
O1S C1S 1.2013(14) . ?
O2S C1S 1.3126(14) . ?
O2S H2S 0.88(2) . ?
C1S H1S 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C1 110.68(9) . . ?
C2 N1 H1N 117.8(11) . . ?
C1 N1 H1N 119.6(11) . . ?
C2 N2 C17 122.86(9) . . ?
C2 N2 C3 112.57(8) . . ?
C17 N2 C3 124.30(9) . . ?
C4 N3 C3 110.97(8) . . ?
C4 N3 C18 122.22(9) . . ?
C3 N3 C18 123.87(8) . . ?
C4 N4 C1 111.48(8) . . ?
C4 N4 H4N 119.6(11) . . ?
C1 N4 H4N 122.9(11) . . ?
N1 C1 N4 113.05(8) . . ?
N1 C1 C5 112.87(8) . . ?
N4 C1 C5 112.69(8) . . ?
N1 C1 C3 101.62(8) . . ?
N4 C1 C3 99.95(8) . . ?
C5 C1 C3 115.59(8) . . ?
O1 C2 N2 125.72(10) . . ?
O1 C2 N1 126.16(10) . . ?
N2 C2 N1 108.09(9) . . ?
N3 C3 N2 112.90(8) . . ?
N3 C3 C11 112.97(8) . . ?
N2 C3 C11 112.79(8) . . ?
N3 C3 C1 101.82(8) . . ?
N2 C3 C1 100.24(8) . . ?
C11 C3 C1 115.02(8) . . ?
O2 C4 N4 125.27(9) . . ?
O2 C4 N3 125.02(10) . . ?
N4 C4 N3 109.71(9) . . ?
C10 C5 C6 118.99(10) . . ?
C10 C5 C1 121.00(9) . . ?
C6 C5 C1 119.93(9) . . ?
C7 C6 C5 120.51(10) . . ?
C7 C6 H6A 119.7 . . ?
C5 C6 H6A 119.7 . . ?
C6 C7 C8 120.13(11) . . ?
C6 C7 H7A 119.9 . . ?
C8 C7 H7A 119.9 . . ?
C9 C8 C7 119.58(10) . . ?
C9 C8 H8A 120.2 . . ?
C7 C8 H8A 120.2 . . ?
C8 C9 C10 120.55(10) . . ?
C8 C9 H9A 119.7 . . ?
C10 C9 H9A 119.7 . . ?
C9 C10 C5 120.24(10) . . ?
C9 C10 H10A 119.9 . . ?
C5 C10 H10A 119.9 . . ?
C12 C11 C16 119.14(10) . . ?
C12 C11 C3 119.80(9) . . ?
C16 C11 C3 120.87(9) . . ?
C11 C12 C13 120.55(10) . . ?
C11 C12 H12A 119.7 . . ?
C13 C12 H12A 119.7 . . ?
C14 C13 C12 120.03(11) . . ?
C14 C13 H13A 120.0 . . ?
C12 C13 H13A 120.0 . . ?
C13 C14 C15 119.89(10) . . ?
C13 C14 H14A 120.1 . . ?
C15 C14 H14A 120.1 . . ?
C14 C15 C16 120.27(11) . . ?
C14 C15 H15A 119.9 . . ?
C16 C15 H15A 119.9 . . ?
C15 C16 C11 120.13(11) . . ?
C15 C16 H16A 119.9 . . ?
C11 C16 H16A 119.9 . . ?
N2 C17 H17A 109.5 . . ?
N2 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
N2 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N3 C18 H18A 109.5 . . ?
N3 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N3 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C1S O2S H2S 109.2(13) . . ?
O1S C1S O2S 124.39(11) . . ?
O1S C1S H1S 117.8 . . ?
O2S C1S H1S 117.8 . . ?

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
C2 N1 C1 N4 -80.42(11) . . . . ?
C2 N1 C1 C5 150.21(9) . . . . ?
C2 N1 C1 C3 25.79(10) . . . . ?
C4 N4 C1 N1 128.36(9) . . . . ?
C4 N4 C1 C5 -102.17(10) . . . . ?
C4 N4 C1 C3 21.10(10) . . . . ?
C17 N2 C2 O1 4.25(16) . . . . ?
C3 N2 C2 O1 178.44(10) . . . . ?
C17 N2 C2 N1 -174.17(9) . . . . ?
C3 N2 C2 N1 0.02(11) . . . . ?
C1 N1 C2 O1 164.02(10) . . . . ?
C1 N1 C2 N2 -17.57(11) . . . . ?
C4 N3 C3 N2 -86.78(10) . . . . ?
C18 N3 C3 N2 74.09(12) . . . . ?
C4 N3 C3 C11 143.74(9) . . . . ?
C18 N3 C3 C11 -55.38(13) . . . . ?
C4 N3 C3 C1 19.81(10) . . . . ?
C18 N3 C3 C1 -179.31(9) . . . . ?
C2 N2 C3 N3 122.63(9) . . . . ?
C17 N2 C3 N3 -63.27(12) . . . . ?
C2 N2 C3 C11 -107.80(10) . . . . ?
C17 N2 C3 C11 66.30(12) . . . . ?
C2 N2 C3 C1 15.03(10) . . . . ?
C17 N2 C3 C1 -170.87(9) . . . . ?
N1 C1 C3 N3 -139.58(8) . . . . ?
N4 C1 C3 N3 -23.36(9) . . . . ?
C5 C1 C3 N3 97.85(9) . . . . ?
N1 C1 C3 N2 -23.36(9) . . . . ?
N4 C1 C3 N2 92.87(8) . . . . ?
C5 C1 C3 N2 -145.93(8) . . . . ?
N1 C1 C3 C11 97.89(9) . . . . ?
N4 C1 C3 C11 -145.89(8) . . . . ?
C5 C1 C3 C11 -24.68(12) . . . . ?
C1 N4 C4 O2 170.29(10) . . . . ?
C1 N4 C4 N3 -10.14(12) . . . . ?
C3 N3 C4 O2 172.12(10) . . . . ?
C18 N3 C4 O2 10.87(16) . . . . ?
C3 N3 C4 N4 -7.45(12) . . . . ?
C18 N3 C4 N4 -168.70(9) . . . . ?
N1 C1 C5 C10 146.68(10) . . . . ?
N4 C1 C5 C10 17.12(13) . . . . ?
C3 C1 C5 C10 -96.95(11) . . . . ?
N1 C1 C5 C6 -36.58(13) . . . . ?
N4 C1 C5 C6 -166.14(9) . . . . ?
C3 C1 C5 C6 79.80(12) . . . . ?
C10 C5 C6 C7 0.57(16) . . . . ?
C1 C5 C6 C7 -176.25(10) . . . . ?
C5 C6 C7 C8 -0.88(17) . . . . ?
C6 C7 C8 C9 0.48(17) . . . . ?
C7 C8 C9 C10 0.24(17) . . . . ?
C8 C9 C10 C5 -0.55(17) . . . . ?
C6 C5 C10 C9 0.15(16) . . . . ?
C1 C5 C10 C9 176.93(10) . . . . ?
N3 C3 C11 C12 154.79(9) . . . . ?
N2 C3 C11 C12 25.25(13) . . . . ?
C1 C3 C11 C12 -88.89(11) . . . . ?
N3 C3 C11 C16 -30.37(13) . . . . ?
N2 C3 C11 C16 -159.90(9) . . . . ?
C1 C3 C11 C16 85.95(12) . . . . ?
C16 C11 C12 C13 0.13(16) . . . . ?
C3 C11 C12 C13 175.06(10) . . . . ?
C11 C12 C13 C14 0.09(17) . . . . ?
C12 C13 C14 C15 -0.42(18) . . . . ?
C13 C14 C15 C16 0.54(18) . . . . ?
C14 C15 C16 C11 -0.32(17) . . . . ?
C12 C11 C16 C15 -0.01(16) . . . . ?
C3 C11 C16 C15 -174.89(10) . . . . ?

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
N1 H1N O1S 0.874(17) 2.084(17) 2.8404(13) 144.3(15) 2_656
N4 H4N O2 0.846(17) 2.079(17) 2.9085(12) 166.8(16) 2_657
O2S H2S O2 0.88(2) 1.80(2) 2.6695(12) 169.8(19) 1_554

_refine_diff_density_max         0.400
_refine_diff_density_min         -0.257
_refine_diff_density_rms         0.050



####################################################################### 
# 
# 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_1a-MeOH
_database_code_depnum_ccdc_archive 'CCDC 2072842'
loop_
_audit_author_name
_audit_author_address
'Valentina Karnoukhova'
;A N Nesmeyanov Institute of Organoelement Compounds of Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2021-03-24 deposited with the CCDC.	2021-05-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H18 N4 O2, C H4 O'
_chemical_formula_sum            'C19 H22 N4 O3'
_chemical_formula_weight         354.40

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.4667(10)
_cell_length_b                   9.5371(10)
_cell_length_c                   10.9139(11)
_cell_angle_alpha                71.045(2)
_cell_angle_beta                 72.014(2)
_cell_angle_gamma                82.789(2)
_cell_volume                     886.04(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    262
_cell_measurement_theta_min      3
_cell_measurement_theta_max      25

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_F_000             376
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.092
_shelx_estimated_absorpt_T_min   0.973
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6892
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker SMART APEX II diffractometer'
_diffrn_detector_type            'Bruker APEX II CCD area detector'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19210
_diffrn_reflns_av_unetI/netI     0.0308
_diffrn_reflns_av_R_equivalents  0.0298
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.059
_diffrn_reflns_theta_max         30.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5177
_reflns_number_gt                4058
_reflns_threshold_expression     I>2σ(I)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015b)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0490P)²+0.2802P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5177
_refine_ls_number_parameters     250
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0588
_refine_ls_R_factor_gt           0.0414
_refine_ls_wR_factor_ref         0.1085
_refine_ls_wR_factor_gt          0.0963
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.90448(10) -0.11789(10) 0.83285(9) 0.02211(19) Uani 1 1 d . . . . .
O2 O 0.97437(9) 0.42100(9) 0.38741(9) 0.02082(19) Uani 1 1 d . . . . .
N1 N 0.80273(11) 0.11835(11) 0.82114(10) 0.0173(2) Uani 1 1 d . . . . .
H1N H 0.8471(19) 0.1349(19) 0.8768(18) 0.035(4) Uiso 1 1 d . . . . .
N2 N 0.79931(11) 0.01848(11) 0.66465(10) 0.0169(2) Uani 1 1 d . . . . .
N3 N 0.78578(11) 0.25423(11) 0.49344(10) 0.01647(19) Uani 1 1 d . . . . .
N4 N 0.88810(11) 0.32645(11) 0.62064(10) 0.01674(19) Uani 1 1 d . . . . .
H4N H 0.9237(18) 0.3979(18) 0.6338(16) 0.028(4) Uiso 1 1 d . . . . .
C1 C 0.76080(12) 0.24227(12) 0.71927(11) 0.0147(2) Uani 1 1 d . . . . .
C2 C 0.84259(12) -0.00389(13) 0.77779(12) 0.0166(2) Uani 1 1 d . . . . .
C3 C 0.71909(12) 0.16028(12) 0.62884(11) 0.0143(2) Uani 1 1 d . . . . .
C4 C 0.89094(12) 0.34199(12) 0.49119(12) 0.0160(2) Uani 1 1 d . . . . .
C5 C 0.63732(12) 0.33798(12) 0.78182(11) 0.0158(2) Uani 1 1 d . . . . .
C6 C 0.52127(13) 0.27127(13) 0.89448(12) 0.0194(2) Uani 1 1 d . . . . .
H6A H 0.524095 0.166940 0.935520 0.023 Uiso 1 1 calc R U . . .
C7 C 0.40196(14) 0.35601(15) 0.94694(13) 0.0239(3) Uani 1 1 d . . . . .
H7A H 0.322759 0.309360 1.022380 0.029 Uiso 1 1 calc R U . . .
C8 C 0.39838(14) 0.50890(15) 0.88916(14) 0.0261(3) Uani 1 1 d . . . . .
H8A H 0.316914 0.567128 0.924868 0.031 Uiso 1 1 calc R U . . .
C9 C 0.51434(14) 0.57604(14) 0.77912(14) 0.0240(3) Uani 1 1 d . . . . .
H9A H 0.512689 0.680756 0.740268 0.029 Uiso 1 1 calc R U . . .
C10 C 0.63321(13) 0.49146(13) 0.72498(12) 0.0198(2) Uani 1 1 d . . . . .
H10A H 0.711747 0.538538 0.649065 0.024 Uiso 1 1 calc R U . . .
C11 C 0.55358(12) 0.14145(13) 0.65772(11) 0.0158(2) Uani 1 1 d . . . . .
C12 C 0.48499(13) 0.01362(13) 0.75251(12) 0.0198(2) Uani 1 1 d . . . . .
H12A H 0.543342 -0.065308 0.793651 0.024 Uiso 1 1 calc R U . . .
C13 C 0.33145(14) 0.00051(15) 0.78753(14) 0.0253(3) Uani 1 1 d . . . . .
H13A H 0.285744 -0.087222 0.851959 0.030 Uiso 1 1 calc R U . . .
C14 C 0.24584(14) 0.11512(17) 0.72849(14) 0.0285(3) Uani 1 1 d . . . . .
H14A H 0.141230 0.106378 0.752519 0.034 Uiso 1 1 calc R U . . .
C15 C 0.31273(14) 0.24286(16) 0.63417(14) 0.0268(3) Uani 1 1 d . . . . .
H15A H 0.253739 0.321743 0.593875 0.032 Uiso 1 1 calc R U . . .
C16 C 0.46619(13) 0.25604(14) 0.59822(12) 0.0202(2) Uani 1 1 d . . . . .
H16A H 0.511465 0.343487 0.532869 0.024 Uiso 1 1 calc R U . . .
C17 C 0.81251(14) -0.09598(13) 0.60002(13) 0.0208(2) Uani 1 1 d . . . . .
H17A H 0.836918 -0.191594 0.659384 0.031 Uiso 1 1 calc R U . . .
H17B H 0.891397 -0.071028 0.514129 0.031 Uiso 1 1 calc R U . . .
H17C H 0.718121 -0.102428 0.583009 0.031 Uiso 1 1 calc R U . . .
C18 C 0.78002(14) 0.22950(14) 0.37023(12) 0.0206(2) Uani 1 1 d . . . . .
H18A H 0.775266 0.325216 0.301830 0.031 Uiso 1 1 calc R U . . .
H18B H 0.691670 0.173327 0.389721 0.031 Uiso 1 1 calc R U . . .
H18C H 0.869260 0.173305 0.336244 0.031 Uiso 1 1 calc R U . . .
O1S O 0.94211(11) 0.20618(11) 0.98020(10) 0.0293(2) Uani 1 1 d . . . . .
H1S H 0.991(2) 0.162(2) 1.038(2) 0.048(5) Uiso 1 1 d . . . . .
C1S C 0.99509(17) 0.35204(15) 0.91756(16) 0.0321(3) Uani 1 1 d . . . . .
H1SA H 1.007809 0.391465 0.985863 0.048 Uiso 1 1 calc R U . . .
H1SB H 0.923396 0.415108 0.873911 0.048 Uiso 1 1 calc R U . . .
H1SC H 1.090783 0.350641 0.849504 0.048 Uiso 1 1 calc R U . . .


_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 C2 1.2327(14) . ?
O2 C4 1.2317(14) . ?
N1 C2 1.3648(15) . ?
N1 C1 1.4462(15) . ?
N1 H1N 0.898(18) . ?
N2 C2 1.3630(15) . ?
N2 C17 1.4547(15) . ?
N2 C3 1.4630(14) . ?
N3 C4 1.3685(14) . ?
N3 C3 1.4460(14) . ?
N3 C18 1.4564(15) . ?
N4 C4 1.3639(15) . ?
N4 C1 1.4615(14) . ?
N4 H4N 0.866(17) . ?
C1 C5 1.5198(16) . ?
C1 C3 1.6004(15) . ?
C3 C11 1.5216(15) . ?
C5 C10 1.3927(16) . ?
C5 C6 1.3988(16) . ?
C6 C7 1.3888(18) . ?
C6 H6A 0.9500 . ?
C7 C8 1.3887(19) . ?
C7 H7A 0.9500 . ?
C8 C9 1.3857(19) . ?
C8 H8A 0.9500 . ?
C9 C10 1.3919(17) . ?
C9 H9A 0.9500 . ?
C10 H10A 0.9500 . ?
C11 C12 1.3938(16) . ?
C11 C16 1.3944(16) . ?
C12 C13 1.3950(17) . ?
C12 H12A 0.9500 . ?
C13 C14 1.382(2) . ?
C13 H13A 0.9500 . ?
C14 C15 1.386(2) . ?
C14 H14A 0.9500 . ?
C15 C16 1.3935(17) . ?
C15 H15A 0.9500 . ?
C16 H16A 0.9500 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
O1S C1S 1.4141(16) . ?
O1S H1S 0.87(2) . ?
C1S H1SA 0.9800 . ?
C1S H1SB 0.9800 . ?
C1S H1SC 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
C2 N1 C1 111.39(10) . . ?
C2 N1 H1N 119.9(11) . . ?
C1 N1 H1N 119.7(11) . . ?
C2 N2 C17 122.90(10) . . ?
C2 N2 C3 112.46(9) . . ?
C17 N2 C3 124.04(10) . . ?
C4 N3 C3 111.49(9) . . ?
C4 N3 C18 121.13(10) . . ?
C3 N3 C18 124.77(9) . . ?
C4 N4 C1 111.87(9) . . ?
C4 N4 H4N 117.0(11) . . ?
C1 N4 H4N 122.3(11) . . ?
N1 C1 N4 112.86(9) . . ?
N1 C1 C5 111.77(9) . . ?
N4 C1 C5 113.59(9) . . ?
N1 C1 C3 101.72(8) . . ?
N4 C1 C3 100.32(8) . . ?
C5 C1 C3 115.56(9) . . ?
O1 C2 N2 125.02(11) . . ?
O1 C2 N1 126.09(11) . . ?
N2 C2 N1 108.87(10) . . ?
N3 C3 N2 113.36(9) . . ?
N3 C3 C11 112.78(9) . . ?
N2 C3 C11 112.49(9) . . ?
N3 C3 C1 101.92(8) . . ?
N2 C3 C1 100.32(8) . . ?
C11 C3 C1 114.95(9) . . ?
O2 C4 N4 126.37(10) . . ?
O2 C4 N3 124.46(11) . . ?
N4 C4 N3 109.17(10) . . ?
C10 C5 C6 118.90(11) . . ?
C10 C5 C1 121.16(10) . . ?
C6 C5 C1 119.86(10) . . ?
C7 C6 C5 120.67(11) . . ?
C7 C6 H6A 119.7 . . ?
C5 C6 H6A 119.7 . . ?
C6 C7 C8 120.03(12) . . ?
C6 C7 H7A 120.0 . . ?
C8 C7 H7A 120.0 . . ?
C9 C8 C7 119.61(12) . . ?
C9 C8 H8A 120.2 . . ?
C7 C8 H8A 120.2 . . ?
C8 C9 C10 120.61(12) . . ?
C8 C9 H9A 119.7 . . ?
C10 C9 H9A 119.7 . . ?
C9 C10 C5 120.17(11) . . ?
C9 C10 H10A 119.9 . . ?
C5 C10 H10A 119.9 . . ?
C12 C11 C16 118.89(11) . . ?
C12 C11 C3 120.23(10) . . ?
C16 C11 C3 120.68(10) . . ?
C11 C12 C13 120.60(12) . . ?
C11 C12 H12A 119.7 . . ?
C13 C12 H12A 119.7 . . ?
C14 C13 C12 120.00(12) . . ?
C14 C13 H13A 120.0 . . ?
C12 C13 H13A 120.0 . . ?
C13 C14 C15 119.93(12) . . ?
C13 C14 H14A 120.0 . . ?
C15 C14 H14A 120.0 . . ?
C14 C15 C16 120.26(12) . . ?
C14 C15 H15A 119.9 . . ?
C16 C15 H15A 119.9 . . ?
C15 C16 C11 120.30(12) . . ?
C15 C16 H16A 119.8 . . ?
C11 C16 H16A 119.8 . . ?
N2 C17 H17A 109.5 . . ?
N2 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
N2 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N3 C18 H18A 109.5 . . ?
N3 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N3 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C1S O1S H1S 106.7(13) . . ?
O1S C1S H1SA 109.5 . . ?
O1S C1S H1SB 109.5 . . ?
H1SA C1S H1SB 109.5 . . ?
O1S C1S H1SC 109.5 . . ?
H1SA C1S H1SC 109.5 . . ?
H1SB C1S H1SC 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
C2 N1 C1 N4 -84.80(11) . . . . ?
C2 N1 C1 C5 145.70(9) . . . . ?
C2 N1 C1 C3 21.83(11) . . . . ?
C4 N4 C1 N1 126.97(10) . . . . ?
C4 N4 C1 C5 -104.47(11) . . . . ?
C4 N4 C1 C3 19.45(11) . . . . ?
C17 N2 C2 O1 4.39(18) . . . . ?
C3 N2 C2 O1 175.80(10) . . . . ?
C17 N2 C2 N1 -174.06(10) . . . . ?
C3 N2 C2 N1 -2.65(13) . . . . ?
C1 N1 C2 O1 168.19(11) . . . . ?
C1 N1 C2 N2 -13.38(13) . . . . ?
C4 N3 C3 N2 -88.40(11) . . . . ?
C18 N3 C3 N2 73.38(13) . . . . ?
C4 N3 C3 C11 142.30(10) . . . . ?
C18 N3 C3 C11 -55.92(14) . . . . ?
C4 N3 C3 C1 18.50(11) . . . . ?
C18 N3 C3 C1 -179.72(10) . . . . ?
C2 N2 C3 N3 123.13(10) . . . . ?
C17 N2 C3 N3 -65.57(13) . . . . ?
C2 N2 C3 C11 -107.42(11) . . . . ?
C17 N2 C3 C11 63.87(14) . . . . ?
C2 N2 C3 C1 15.23(11) . . . . ?
C17 N2 C3 C1 -173.48(10) . . . . ?
N1 C1 C3 N3 -137.88(9) . . . . ?
N4 C1 C3 N3 -21.70(10) . . . . ?
C5 C1 C3 N3 100.85(10) . . . . ?
N1 C1 C3 N2 -21.11(10) . . . . ?
N4 C1 C3 N2 95.07(9) . . . . ?
C5 C1 C3 N2 -142.38(9) . . . . ?
N1 C1 C3 C11 99.79(10) . . . . ?
N4 C1 C3 C11 -144.03(9) . . . . ?
C5 C1 C3 C11 -21.48(13) . . . . ?
C1 N4 C4 O2 171.16(11) . . . . ?
C1 N4 C4 N3 -9.23(13) . . . . ?
C3 N3 C4 O2 172.42(10) . . . . ?
C18 N3 C4 O2 9.88(18) . . . . ?
C3 N3 C4 N4 -7.20(13) . . . . ?
C18 N3 C4 N4 -169.74(10) . . . . ?
N1 C1 C5 C10 143.85(11) . . . . ?
N4 C1 C5 C10 14.73(15) . . . . ?
C3 C1 C5 C10 -100.46(12) . . . . ?
N1 C1 C5 C6 -39.38(14) . . . . ?
N4 C1 C5 C6 -168.50(10) . . . . ?
C3 C1 C5 C6 76.31(13) . . . . ?
C10 C5 C6 C7 1.59(17) . . . . ?
C1 C5 C6 C7 -175.25(11) . . . . ?
C5 C6 C7 C8 -1.25(19) . . . . ?
C6 C7 C8 C9 0.0(2) . . . . ?
C7 C8 C9 C10 0.9(2) . . . . ?
C8 C9 C10 C5 -0.51(19) . . . . ?
C6 C5 C10 C9 -0.71(17) . . . . ?
C1 C5 C10 C9 176.09(11) . . . . ?
N3 C3 C11 C12 152.46(10) . . . . ?
N2 C3 C11 C12 22.71(15) . . . . ?
C1 C3 C11 C12 -91.27(13) . . . . ?
N3 C3 C11 C16 -32.68(15) . . . . ?
N2 C3 C11 C16 -162.42(10) . . . . ?
C1 C3 C11 C16 83.59(13) . . . . ?
C16 C11 C12 C13 -0.11(18) . . . . ?
C3 C11 C12 C13 174.85(11) . . . . ?
C11 C12 C13 C14 -0.26(19) . . . . ?
C12 C13 C14 C15 0.2(2) . . . . ?
C13 C14 C15 C16 0.2(2) . . . . ?
C14 C15 C16 C11 -0.6(2) . . . . ?
C12 C11 C16 C15 0.54(18) . . . . ?
C3 C11 C16 C15 -174.39(11) . . . . ?

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
N1 H1N O1S 0.898(18) 1.955(18) 2.8448(14) 170.3(16) .
N4 H4N O2 0.866(17) 1.997(17) 2.8432(13) 165.3(15) 2_766
O1S H1S O1 0.87(2) 1.87(2) 2.7181(13) 164.3(19) 2_757

_refine_diff_density_max         0.375
_refine_diff_density_min         -0.224
_refine_diff_density_rms         0.046



####################################################################### 
# 
# 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_1a-dioxane
_database_code_depnum_ccdc_archive 'CCDC 2072849'
loop_
_audit_author_name
_audit_author_address
'Valentina Karnoukhova'
;A N Nesmeyanov Institute of Organoelement Compounds of Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2021-03-24 deposited with the CCDC.	2021-05-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H18 N4 O2, 1.5(C4 H8 O2)'
_chemical_formula_sum            'C24 H30 N4 O5'
_chemical_formula_weight         454.52

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.8013(8)
_cell_length_b                   14.8820(11)
_cell_length_c                   16.5499(12)
_cell_angle_alpha                100.2147(16)
_cell_angle_beta                 108.5370(16)
_cell_angle_gamma                109.0343(17)
_cell_volume                     2264.1(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    999
_cell_measurement_theta_min      3
_cell_measurement_theta_max      25

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.333
_exptl_crystal_F_000             968
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.170
_exptl_absorpt_coefficient_mu    0.095
_shelx_estimated_absorpt_T_min   0.977
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6805
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX DUO diffractometer'
_diffrn_detector_type            'Bruker APEX II CCD area detector'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            50823
_diffrn_reflns_av_unetI/netI     0.0634
_diffrn_reflns_av_R_equivalents  0.0663
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.053
_diffrn_reflns_theta_max         30.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             13207
_reflns_number_gt                8478
_reflns_threshold_expression     I>2σ(I)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015b)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0490P)²+0.2318P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         13207
_refine_ls_number_parameters     652
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0900
_refine_ls_R_factor_gt           0.0500
_refine_ls_wR_factor_ref         0.1257
_refine_ls_wR_factor_gt          0.1057
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.020
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

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 0.50603(11) 0.23596(8) 0.36646(7) 0.0221(2) Uani 1 1 d . . . . .
O2 O 1.05857(11) 0.26106(8) 0.37238(7) 0.0229(2) Uani 1 1 d . . . . .
N1 N 0.61677(14) 0.19302(9) 0.27656(8) 0.0184(3) Uani 1 1 d . . . . .
H1N H 0.5658(19) 0.2051(13) 0.2306(12) 0.030(5) Uiso 1 1 d . . . . .
N2 N 0.63233(13) 0.13880(9) 0.39450(8) 0.0177(2) Uani 1 1 d . . . . .
N3 N 0.87475(13) 0.17341(9) 0.40701(8) 0.0192(3) Uani 1 1 d . . . . .
N4 N 0.82588(13) 0.17346(9) 0.26680(8) 0.0185(3) Uani 1 1 d . . . . .
H4N H 0.8392(19) 0.1990(13) 0.2251(12) 0.031(5) Uiso 1 1 d . . . . .
C1 C 0.68525(15) 0.12456(10) 0.26546(9) 0.0159(3) Uani 1 1 d . . . . .
C2 C 0.57770(15) 0.19327(10) 0.34688(9) 0.0175(3) Uani 1 1 d . . . . .
C3 C 0.72313(15) 0.10506(10) 0.36050(9) 0.0164(3) Uani 1 1 d . . . . .
C4 C 0.93128(15) 0.20850(10) 0.35030(10) 0.0181(3) Uani 1 1 d . . . . .
C5 C 0.58821(15) 0.03376(10) 0.18276(9) 0.0165(3) Uani 1 1 d . . . . .
C6 C 0.44030(16) -0.00148(11) 0.15377(10) 0.0219(3) Uani 1 1 d . . . . .
H6A H 0.400562 0.029948 0.187364 0.026 Uiso 1 1 calc R U . . .
C7 C 0.35038(17) -0.08166(11) 0.07668(11) 0.0253(3) Uani 1 1 d . . . . .
H7A H 0.249575 -0.105349 0.058041 0.030 Uiso 1 1 calc R U . . .
C8 C 0.40664(17) -0.12749(11) 0.02663(10) 0.0244(3) Uani 1 1 d . . . . .
H8A H 0.344854 -0.181464 -0.027192 0.029 Uiso 1 1 calc R U . . .
C9 C 0.55348(18) -0.09421(12) 0.05546(11) 0.0255(3) Uani 1 1 d . . . . .
H9A H 0.592686 -0.126141 0.021824 0.031 Uiso 1 1 calc R U . . .
C10 C 0.64383(17) -0.01439(11) 0.13328(10) 0.0220(3) Uani 1 1 d . . . . .
H10A H 0.744595 0.007539 0.152913 0.026 Uiso 1 1 calc R U . . .
C11 C 0.70076(15) -0.00152(11) 0.35757(9) 0.0178(3) Uani 1 1 d . . . . .
C12 C 0.58208(16) -0.06582(11) 0.36552(10) 0.0211(3) Uani 1 1 d . . . . .
H12A H 0.512066 -0.043422 0.372470 0.025 Uiso 1 1 calc R U . . .
C13 C 0.56567(18) -0.16290(12) 0.36330(10) 0.0263(3) Uani 1 1 d . . . . .
H13A H 0.485385 -0.206070 0.370152 0.032 Uiso 1 1 calc R U . . .
C14 C 0.66454(19) -0.19719(12) 0.35128(11) 0.0288(4) Uani 1 1 d . . . . .
H14A H 0.653049 -0.263496 0.350294 0.035 Uiso 1 1 calc R U . . .
C15 C 0.78095(18) -0.13429(12) 0.34064(11) 0.0286(4) Uani 1 1 d . . . . .
H15A H 0.848407 -0.157945 0.330922 0.034 Uiso 1 1 calc R U . . .
C16 C 0.79899(17) -0.03724(12) 0.34414(10) 0.0236(3) Uani 1 1 d . . . . .
H16A H 0.879490 0.005638 0.337290 0.028 Uiso 1 1 calc R U . . .
C17 C 0.64143(17) 0.14934(12) 0.48529(10) 0.0237(3) Uani 1 1 d . . . . .
H17A H 0.663830 0.095956 0.504772 0.036 Uiso 1 1 calc R U . . .
H17B H 0.549627 0.144640 0.486840 0.036 Uiso 1 1 calc R U . . .
H17C H 0.716988 0.214554 0.525586 0.036 Uiso 1 1 calc R U . . .
C18 C 0.96658(17) 0.18357(13) 0.49691(10) 0.0269(4) Uani 1 1 d . . . . .
H18A H 0.931419 0.120450 0.509703 0.040 Uiso 1 1 calc R U . . .
H18B H 0.965848 0.237208 0.540464 0.040 Uiso 1 1 calc R U . . .
H18C H 1.064514 0.199920 0.501305 0.040 Uiso 1 1 calc R U . . .
O1A O -0.08871(11) 0.26497(8) 0.14739(7) 0.0216(2) Uani 1 1 d . . . . .
O2A O 0.42686(11) 0.23096(8) 0.13452(7) 0.0233(2) Uani 1 1 d . . . . .
N1A N 0.14927(13) 0.33835(9) 0.24628(8) 0.0188(3) Uani 1 1 d . . . . .
H1NA H 0.1317(18) 0.3162(12) 0.2910(12) 0.027(5) Uiso 1 1 d . . . . .
N2A N 0.09425(13) 0.33493(9) 0.10511(8) 0.0184(3) Uani 1 1 d . . . . .
N3A N 0.32369(13) 0.34158(9) 0.10783(8) 0.0184(3) Uani 1 1 d . . . . .
N4A N 0.34207(14) 0.29758(9) 0.23100(8) 0.0182(3) Uani 1 1 d . . . . .
H4NA H 0.395(2) 0.2842(14) 0.2791(13) 0.042(6) Uiso 1 1 d . . . . .
C1A C 0.28835(15) 0.37506(10) 0.24273(9) 0.0162(3) Uani 1 1 d . . . . .
C2A C 0.04024(16) 0.30786(10) 0.16491(10) 0.0176(3) Uani 1 1 d . . . . .
C3A C 0.24964(15) 0.39035(10) 0.14594(9) 0.0166(3) Uani 1 1 d . . . . .
C4A C 0.36949(15) 0.28476(10) 0.15618(10) 0.0182(3) Uani 1 1 d . . . . .
C5A C 0.39625(15) 0.46622(10) 0.32318(9) 0.0171(3) Uani 1 1 d . . . . .
C6A C 0.35144(17) 0.52455(11) 0.37226(10) 0.0225(3) Uani 1 1 d . . . . .
H6AA H 0.252239 0.509475 0.353821 0.027 Uiso 1 1 calc R U . . .
C7A C 0.45034(18) 0.60486(12) 0.44818(11) 0.0267(3) Uani 1 1 d . . . . .
H7AA H 0.418515 0.644188 0.481516 0.032 Uiso 1 1 calc R U . . .
C8A C 0.59480(18) 0.62767(11) 0.47531(10) 0.0263(3) Uani 1 1 d . . . . .
H8AA H 0.662213 0.681887 0.527840 0.032 Uiso 1 1 calc R U . . .
C9A C 0.64110(17) 0.57138(11) 0.42581(11) 0.0259(3) Uani 1 1 d . . . . .
H9AA H 0.740579 0.587843 0.443683 0.031 Uiso 1 1 calc R U . . .
C10A C 0.54255(16) 0.49093(11) 0.35009(10) 0.0220(3) Uani 1 1 d . . . . .
H10B H 0.574898 0.452441 0.316387 0.026 Uiso 1 1 calc R U . . .
C11A C 0.29292(16) 0.49853(11) 0.14645(9) 0.0193(3) Uani 1 1 d . . . . .
C12A C 0.20491(18) 0.54696(11) 0.15403(10) 0.0244(3) Uani 1 1 d . . . . .
H12B H 0.116909 0.511842 0.157589 0.029 Uiso 1 1 calc R U . . .
C13A C 0.2446(2) 0.64617(12) 0.15645(11) 0.0308(4) Uani 1 1 d . . . . .
H13B H 0.183946 0.678770 0.161851 0.037 Uiso 1 1 calc R U . . .
C14A C 0.3721(2) 0.69784(12) 0.15105(11) 0.0346(4) Uani 1 1 d . . . . .
H14B H 0.399009 0.765707 0.152280 0.041 Uiso 1 1 calc R U . . .
C15A C 0.4599(2) 0.65021(12) 0.14386(11) 0.0339(4) Uani 1 1 d . . . . .
H15B H 0.547411 0.685471 0.139761 0.041 Uiso 1 1 calc R U . . .
C16A C 0.42209(18) 0.55137(11) 0.14254(11) 0.0263(3) Uani 1 1 d . . . . .
H16B H 0.484543 0.519754 0.138958 0.032 Uiso 1 1 calc R U . . .
C17A C 0.00318(17) 0.32054(11) 0.01366(10) 0.0229(3) Uani 1 1 d . . . . .
H17D H 0.045979 0.377982 -0.004698 0.034 Uiso 1 1 calc R U . . .
H17E H -0.091522 0.314595 0.010307 0.034 Uiso 1 1 calc R U . . .
H17F H -0.006420 0.259334 -0.026391 0.034 Uiso 1 1 calc R U . . .
C18A C 0.3049(2) 0.32247(12) 0.01464(10) 0.0287(4) Uani 1 1 d . . . . .
H18D H 0.290945 0.377650 -0.005941 0.043 Uiso 1 1 calc R U . . .
H18E H 0.220944 0.259733 -0.022222 0.043 Uiso 1 1 calc R U . . .
H18F H 0.390176 0.317147 0.009198 0.043 Uiso 1 1 calc R U . . .
O1S O 0.70900(14) 0.47772(9) 0.21095(9) 0.0401(3) Uani 1 1 d . . . . .
O2S O 0.89860(15) 0.57137(10) 0.13775(9) 0.0445(3) Uani 1 1 d . . . . .
C1S C 0.6843(3) 0.4437(2) 0.1130(2) 0.0298(8) Uani 0.560(3) 1 d . . P A 1
H1SA H 0.629754 0.476782 0.079155 0.036 Uiso 0.560(3) 1 calc R U P A 1
H1SB H 0.626855 0.370477 0.087319 0.036 Uiso 0.560(3) 1 calc R U P A 1
C2S C 0.8259(5) 0.4693(6) 0.1032(5) 0.0296(11) Uani 0.560(3) 1 d . . P A 1
H2SA H 0.881539 0.436498 0.136654 0.036 Uiso 0.560(3) 1 calc R U P A 1
H2SB H 0.809134 0.446233 0.039269 0.036 Uiso 0.560(3) 1 calc R U P A 1
C3S C 0.9349(4) 0.6056(2) 0.2317(2) 0.0357(9) Uani 0.560(3) 1 d . . P A 1
H3SA H 0.993260 0.678764 0.256258 0.043 Uiso 0.560(3) 1 calc R U P A 1
H3SB H 0.990462 0.571855 0.263514 0.043 Uiso 0.560(3) 1 calc R U P A 1
C4S C 0.7943(12) 0.5803(9) 0.2433(8) 0.0384(19) Uani 0.560(3) 1 d . . P A 1
H4SA H 0.815310 0.605439 0.307795 0.046 Uiso 0.560(3) 1 calc R U P A 1
H4SB H 0.740656 0.614901 0.211194 0.046 Uiso 0.560(3) 1 calc R U P A 1
C1S' C 0.7581(5) 0.4210(3) 0.1646(3) 0.0380(12) Uani 0.440(3) 1 d . . P A 2
H1SC H 0.687952 0.350243 0.137469 0.046 Uiso 0.440(3) 1 calc R U P A 2
H1SD H 0.850556 0.424020 0.204768 0.046 Uiso 0.440(3) 1 calc R U P A 2
C2S' C 0.7753(8) 0.4667(8) 0.0947(7) 0.0394(18) Uani 0.440(3) 1 d . . P A 2
H2SC H 0.685437 0.471750 0.060727 0.047 Uiso 0.440(3) 1 calc R U P A 2
H2SD H 0.795789 0.423956 0.052167 0.047 Uiso 0.440(3) 1 calc R U P A 2
C3S' C 0.8372(5) 0.6243(3) 0.1912(3) 0.0396(12) Uani 0.440(3) 1 d . . P A 2
H3SC H 0.902636 0.696120 0.219377 0.048 Uiso 0.440(3) 1 calc R U P A 2
H3SD H 0.743770 0.619229 0.150358 0.048 Uiso 0.440(3) 1 calc R U P A 2
C4S' C 0.8186(18) 0.5809(12) 0.2592(11) 0.057(4) Uani 0.440(3) 1 d . . P A 2
H4SC H 0.786173 0.618967 0.297112 0.068 Uiso 0.440(3) 1 calc R U P A 2
H4SD H 0.909628 0.580645 0.298001 0.068 Uiso 0.440(3) 1 calc R U P A 2
O3S O -0.00114(14) 0.55554(9) 0.43883(10) 0.0452(4) Uani 1 1 d . . . . .
O4S O 0.97229(12) 0.90112(8) 1.00389(8) 0.0281(3) Uani 1 1 d . . . . .
C5S C -0.0805(2) 0.44921(14) 0.40980(15) 0.0494(6) Uani 1 1 d . . . . .
H5SA H -0.021662 0.415501 0.394834 0.059 Uiso 1 1 calc R U . . .
H5SB H -0.167900 0.429248 0.354965 0.059 Uiso 1 1 calc R U . . .
C6S C 0.1212(2) 0.58316(14) 0.51888(15) 0.0478(5) Uani 1 1 d . . . . .
H6SA H 0.175537 0.656743 0.540276 0.057 Uiso 1 1 calc R U . . .
H6SB H 0.184177 0.552151 0.506279 0.057 Uiso 1 1 calc R U . . .
C7S C 1.01103(19) 0.93340(12) 0.93581(11) 0.0277(4) Uani 1 1 d . . . . .
H7SA H 0.923290 0.917495 0.882531 0.033 Uiso 1 1 calc R U . . .
H7SB H 1.064626 0.896873 0.917557 0.033 Uiso 1 1 calc R U . . .
C8S C 0.89848(17) 0.95624(12) 1.03140(11) 0.0259(3) Uani 1 1 d . . . . .
H8SA H 0.873708 0.935737 1.079927 0.031 Uiso 1 1 calc R U . . .
H8SB H 0.808293 0.940794 0.980176 0.031 Uiso 1 1 calc R U . . .
O5S O 0.29289(13) 0.98571(9) 0.37116(8) 0.0350(3) Uani 1 1 d . . . . .
O6S O 0.03825(13) 0.97561(10) 0.24413(8) 0.0359(3) Uani 1 1 d . . . . .
C9S C 0.23294(19) 1.05564(13) 0.38883(12) 0.0331(4) Uani 1 1 d . . . . .
H9SA H 0.310558 1.120964 0.429709 0.040 Uiso 1 1 calc R U . . .
H9SB H 0.168481 1.031347 0.418786 0.040 Uiso 1 1 calc R U . . .
C10S C 0.15119(19) 1.06857(13) 0.30367(12) 0.0338(4) Uani 1 1 d . . . . .
H10C H 0.110974 1.117603 0.316958 0.041 Uiso 1 1 calc R U . . .
H10D H 0.216380 1.095013 0.274753 0.041 Uiso 1 1 calc R U . . .
C11S C 0.0980(2) 0.90664(14) 0.22509(12) 0.0347(4) Uani 1 1 d . . . . .
H11A H 0.161294 0.931696 0.194636 0.042 Uiso 1 1 calc R U . . .
H11B H 0.020260 0.841431 0.184061 0.042 Uiso 1 1 calc R U . . .
C12S C 0.18215(19) 0.89264(13) 0.30964(12) 0.0339(4) Uani 1 1 d . . . . .
H12C H 0.117387 0.863047 0.337815 0.041 Uiso 1 1 calc R U . . .
H12D H 0.224820 0.845686 0.295040 0.041 Uiso 1 1 calc R U . . .


_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 C2 1.2310(17) . ?
O2 C4 1.2302(17) . ?
N1 C2 1.3580(18) . ?
N1 C1 1.4597(18) . ?
N1 H1N 0.873(19) . ?
N2 C2 1.3672(18) . ?
N2 C3 1.4501(18) . ?
N2 C17 1.4506(18) . ?
N3 C4 1.3626(18) . ?
N3 C18 1.4507(19) . ?
N3 C3 1.4640(18) . ?
N4 C4 1.3544(19) . ?
N4 C1 1.4453(18) . ?
N4 H4N 0.873(18) . ?
C1 C5 1.5185(19) . ?
C1 C3 1.5988(19) . ?
C3 C11 1.514(2) . ?
C5 C10 1.389(2) . ?
C5 C6 1.391(2) . ?
C6 C7 1.382(2) . ?
C6 H6A 0.9500 . ?
C7 C8 1.382(2) . ?
C7 H7A 0.9500 . ?
C8 C9 1.382(2) . ?
C8 H8A 0.9500 . ?
C9 C10 1.387(2) . ?
C9 H9A 0.9500 . ?
C10 H10A 0.9500 . ?
C11 C12 1.389(2) . ?
C11 C16 1.391(2) . ?
C12 C13 1.389(2) . ?
C12 H12A 0.9500 . ?
C13 C14 1.377(2) . ?
C13 H13A 0.9500 . ?
C14 C15 1.386(2) . ?
C14 H14A 0.9500 . ?
C15 C16 1.381(2) . ?
C15 H15A 0.9500 . ?
C16 H16A 0.9500 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
O1A C2A 1.2366(17) . ?
O2A C4A 1.2314(17) . ?
N1A C2A 1.3538(18) . ?
N1A C1A 1.4460(18) . ?
N1A H1NA 0.909(18) . ?
N2A C2A 1.3554(18) . ?
N2A C17A 1.4508(18) . ?
N2A C3A 1.4602(18) . ?
N3A C4A 1.3642(18) . ?
N3A C3A 1.4497(18) . ?
N3A C18A 1.4521(18) . ?
N4A C4A 1.3579(18) . ?
N4A C1A 1.4603(18) . ?
N4A H4NA 0.92(2) . ?
C1A C5A 1.521(2) . ?
C1A C3A 1.5994(19) . ?
C3A C11A 1.521(2) . ?
C5A C6A 1.386(2) . ?
C5A C10A 1.395(2) . ?
C6A C7A 1.389(2) . ?
C6A H6AA 0.9500 . ?
C7A C8A 1.381(2) . ?
C7A H7AA 0.9500 . ?
C8A C9A 1.383(2) . ?
C8A H8AA 0.9500 . ?
C9A C10A 1.388(2) . ?
C9A H9AA 0.9500 . ?
C10A H10B 0.9500 . ?
C11A C16A 1.389(2) . ?
C11A C12A 1.389(2) . ?
C12A C13A 1.386(2) . ?
C12A H12B 0.9500 . ?
C13A C14A 1.381(3) . ?
C13A H13B 0.9500 . ?
C14A C15A 1.377(3) . ?
C14A H14B 0.9500 . ?
C15A C16A 1.386(2) . ?
C15A H15B 0.9500 . ?
C16A H16B 0.9500 . ?
C17A H17D 0.9800 . ?
C17A H17E 0.9800 . ?
C17A H17F 0.9800 . ?
C18A H18D 0.9800 . ?
C18A H18E 0.9800 . ?
C18A H18F 0.9800 . ?
O1S C1S' 1.379(4) . ?
O1S C4S 1.394(13) . ?
O1S C4S' 1.475(17) . ?
O1S C1S 1.517(3) . ?
O2S C2S 1.371(8) . ?
O2S C3S 1.425(3) . ?
O2S C3S' 1.520(5) . ?
O2S C2S' 1.536(10) . ?
C1S C2S 1.520(6) . ?
C1S H1SA 0.9900 . ?
C1S H1SB 0.9900 . ?
C2S H2SA 0.9900 . ?
C2S H2SB 0.9900 . ?
C3S C4S 1.524(10) . ?
C3S H3SA 0.9900 . ?
C3S H3SB 0.9900 . ?
C4S H4SA 0.9900 . ?
C4S H4SB 0.9900 . ?
C1S' C2S' 1.473(11) . ?
C1S' H1SC 0.9900 . ?
C1S' H1SD 0.9900 . ?
C2S' H2SC 0.9900 . ?
C2S' H2SD 0.9900 . ?
C3S' C4S' 1.428(17) . ?
C3S' H3SC 0.9900 . ?
C3S' H3SD 0.9900 . ?
C4S' H4SC 0.9900 . ?
C4S' H4SD 0.9900 . ?
O3S C6S 1.418(2) . ?
O3S C5S 1.433(2) . ?
O4S C7S 1.4268(19) . ?
O4S C8S 1.4285(18) . ?
C5S C6S 1.487(3) 2_566 ?
C5S H5SA 0.9900 . ?
C5S H5SB 0.9900 . ?
C6S H6SA 0.9900 . ?
C6S H6SB 0.9900 . ?
C7S C8S 1.499(2) 2_777 ?
C7S H7SA 0.9900 . ?
C7S H7SB 0.9900 . ?
C8S H8SA 0.9900 . ?
C8S H8SB 0.9900 . ?
O5S C12S 1.425(2) . ?
O5S C9S 1.428(2) . ?
O6S C11S 1.420(2) . ?
O6S C10S 1.423(2) . ?
C9S C10S 1.490(3) . ?
C9S H9SA 0.9900 . ?
C9S H9SB 0.9900 . ?
C10S H10C 0.9900 . ?
C10S H10D 0.9900 . ?
C11S C12S 1.499(3) . ?
C11S H11A 0.9900 . ?
C11S H11B 0.9900 . ?
C12S H12C 0.9900 . ?
C12S H12D 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C1 112.51(12) . . ?
C2 N1 H1N 118.3(12) . . ?
C1 N1 H1N 121.4(12) . . ?
C2 N2 C3 112.15(11) . . ?
C2 N2 C17 120.23(12) . . ?
C3 N2 C17 123.57(12) . . ?
C4 N3 C18 120.94(12) . . ?
C4 N3 C3 112.54(12) . . ?
C18 N3 C3 124.64(12) . . ?
C4 N4 C1 112.69(12) . . ?
C4 N4 H4N 120.5(12) . . ?
C1 N4 H4N 122.4(12) . . ?
N4 C1 N1 112.83(11) . . ?
N4 C1 C5 112.44(11) . . ?
N1 C1 C5 111.15(12) . . ?
N4 C1 C3 101.80(11) . . ?
N1 C1 C3 100.96(11) . . ?
C5 C1 C3 116.94(11) . . ?
O1 C2 N1 126.45(14) . . ?
O1 C2 N2 124.46(13) . . ?
N1 C2 N2 109.08(12) . . ?
N2 C3 N3 112.96(11) . . ?
N2 C3 C11 113.18(11) . . ?
N3 C3 C11 111.43(12) . . ?
N2 C3 C1 102.06(11) . . ?
N3 C3 C1 100.87(11) . . ?
C11 C3 C1 115.47(11) . . ?
O2 C4 N4 126.55(13) . . ?
O2 C4 N3 124.55(13) . . ?
N4 C4 N3 108.87(12) . . ?
C10 C5 C6 118.54(13) . . ?
C10 C5 C1 121.34(13) . . ?
C6 C5 C1 120.11(13) . . ?
C7 C6 C5 120.83(14) . . ?
C7 C6 H6A 119.6 . . ?
C5 C6 H6A 119.6 . . ?
C8 C7 C6 120.23(15) . . ?
C8 C7 H7A 119.9 . . ?
C6 C7 H7A 119.9 . . ?
C9 C8 C7 119.51(14) . . ?
C9 C8 H8A 120.2 . . ?
C7 C8 H8A 120.2 . . ?
C8 C9 C10 120.31(15) . . ?
C8 C9 H9A 119.8 . . ?
C10 C9 H9A 119.8 . . ?
C9 C10 C5 120.56(14) . . ?
C9 C10 H10A 119.7 . . ?
C5 C10 H10A 119.7 . . ?
C12 C11 C16 118.86(14) . . ?
C12 C11 C3 121.61(13) . . ?
C16 C11 C3 119.51(13) . . ?
C11 C12 C13 120.04(14) . . ?
C11 C12 H12A 120.0 . . ?
C13 C12 H12A 120.0 . . ?
C14 C13 C12 120.68(15) . . ?
C14 C13 H13A 119.7 . . ?
C12 C13 H13A 119.7 . . ?
C13 C14 C15 119.52(15) . . ?
C13 C14 H14A 120.2 . . ?
C15 C14 H14A 120.2 . . ?
C16 C15 C14 120.06(15) . . ?
C16 C15 H15A 120.0 . . ?
C14 C15 H15A 120.0 . . ?
C15 C16 C11 120.80(15) . . ?
C15 C16 H16A 119.6 . . ?
C11 C16 H16A 119.6 . . ?
N2 C17 H17A 109.5 . . ?
N2 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
N2 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N3 C18 H18A 109.5 . . ?
N3 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N3 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C2A N1A C1A 112.81(12) . . ?
C2A N1A H1NA 119.2(11) . . ?
C1A N1A H1NA 124.5(11) . . ?
C2A N2A C17A 122.25(12) . . ?
C2A N2A C3A 112.72(11) . . ?
C17A N2A C3A 124.59(12) . . ?
C4A N3A C3A 112.18(11) . . ?
C4A N3A C18A 120.35(12) . . ?
C3A N3A C18A 123.58(12) . . ?
C4A N4A C1A 112.75(12) . . ?
C4A N4A H4NA 118.1(12) . . ?
C1A N4A H4NA 121.9(12) . . ?
N1A C1A N4A 113.00(11) . . ?
N1A C1A C5A 111.68(11) . . ?
N4A C1A C5A 111.66(12) . . ?
N1A C1A C3A 101.67(11) . . ?
N4A C1A C3A 100.97(11) . . ?
C5A C1A C3A 117.17(11) . . ?
O1A C2A N1A 126.19(13) . . ?
O1A C2A N2A 124.69(13) . . ?
N1A C2A N2A 109.08(12) . . ?
N3A C3A N2A 113.49(11) . . ?
N3A C3A C11A 112.30(12) . . ?
N2A C3A C11A 111.45(12) . . ?
N3A C3A C1A 102.33(11) . . ?
N2A C3A C1A 101.29(11) . . ?
C11A C3A C1A 115.28(11) . . ?
O2A C4A N4A 126.12(14) . . ?
O2A C4A N3A 124.66(13) . . ?
N4A C4A N3A 109.22(12) . . ?
C6A C5A C10A 118.88(14) . . ?
C6A C5A C1A 120.91(13) . . ?
C10A C5A C1A 120.19(13) . . ?
C5A C6A C7A 120.56(15) . . ?
C5A C6A H6AA 119.7 . . ?
C7A C6A H6AA 119.7 . . ?
C8A C7A C6A 120.17(15) . . ?
C8A C7A H7AA 119.9 . . ?
C6A C7A H7AA 119.9 . . ?
C7A C8A C9A 119.83(15) . . ?
C7A C8A H8AA 120.1 . . ?
C9A C8A H8AA 120.1 . . ?
C8A C9A C10A 120.13(15) . . ?
C8A C9A H9AA 119.9 . . ?
C10A C9A H9AA 119.9 . . ?
C9A C10A C5A 120.40(14) . . ?
C9A C10A H10B 119.8 . . ?
C5A C10A H10B 119.8 . . ?
C16A C11A C12A 119.04(14) . . ?
C16A C11A C3A 121.02(14) . . ?
C12A C11A C3A 119.90(14) . . ?
C13A C12A C11A 120.43(16) . . ?
C13A C12A H12B 119.8 . . ?
C11A C12A H12B 119.8 . . ?
C14A C13A C12A 120.27(16) . . ?
C14A C13A H13B 119.9 . . ?
C12A C13A H13B 119.9 . . ?
C15A C14A C13A 119.49(15) . . ?
C15A C14A H14B 120.3 . . ?
C13A C14A H14B 120.3 . . ?
C14A C15A C16A 120.71(17) . . ?
C14A C15A H15B 119.6 . . ?
C16A C15A H15B 119.6 . . ?
C15A C16A C11A 120.05(16) . . ?
C15A C16A H16B 120.0 . . ?
C11A C16A H16B 120.0 . . ?
N2A C17A H17D 109.5 . . ?
N2A C17A H17E 109.5 . . ?
H17D C17A H17E 109.5 . . ?
N2A C17A H17F 109.5 . . ?
H17D C17A H17F 109.5 . . ?
H17E C17A H17F 109.5 . . ?
N3A C18A H18D 109.5 . . ?
N3A C18A H18E 109.5 . . ?
H18D C18A H18E 109.5 . . ?
N3A C18A H18F 109.5 . . ?
H18D C18A H18F 109.5 . . ?
H18E C18A H18F 109.5 . . ?
C1S' O1S C4S' 111.3(6) . . ?
C4S O1S C1S 106.3(5) . . ?
C2S O2S C3S 111.5(4) . . ?
C3S' O2S C2S' 99.9(4) . . ?
O1S C1S C2S 110.7(4) . . ?
O1S C1S H1SA 109.5 . . ?
C2S C1S H1SA 109.5 . . ?
O1S C1S H1SB 109.5 . . ?
C2S C1S H1SB 109.5 . . ?
H1SA C1S H1SB 108.1 . . ?
O2S C2S C1S 106.7(5) . . ?
O2S C2S H2SA 110.4 . . ?
C1S C2S H2SA 110.4 . . ?
O2S C2S H2SB 110.4 . . ?
C1S C2S H2SB 110.4 . . ?
H2SA C2S H2SB 108.6 . . ?
O2S C3S C4S 106.7(5) . . ?
O2S C3S H3SA 110.4 . . ?
C4S C3S H3SA 110.4 . . ?
O2S C3S H3SB 110.4 . . ?
C4S C3S H3SB 110.4 . . ?
H3SA C3S H3SB 108.6 . . ?
O1S C4S C3S 112.6(7) . . ?
O1S C4S H4SA 109.1 . . ?
C3S C4S H4SA 109.1 . . ?
O1S C4S H4SB 109.1 . . ?
C3S C4S H4SB 109.1 . . ?
H4SA C4S H4SB 107.8 . . ?
O1S C1S' C2S' 104.4(5) . . ?
O1S C1S' H1SC 110.9 . . ?
C2S' C1S' H1SC 110.9 . . ?
O1S C1S' H1SD 110.9 . . ?
C2S' C1S' H1SD 110.9 . . ?
H1SC C1S' H1SD 108.9 . . ?
C1S' C2S' O2S 110.0(7) . . ?
C1S' C2S' H2SC 109.7 . . ?
O2S C2S' H2SC 109.7 . . ?
C1S' C2S' H2SD 109.7 . . ?
O2S C2S' H2SD 109.7 . . ?
H2SC C2S' H2SD 108.2 . . ?
C4S' C3S' O2S 110.8(7) . . ?
C4S' C3S' H3SC 109.5 . . ?
O2S C3S' H3SC 109.5 . . ?
C4S' C3S' H3SD 109.5 . . ?
O2S C3S' H3SD 109.5 . . ?
H3SC C3S' H3SD 108.1 . . ?
C3S' C4S' O1S 105.6(11) . . ?
C3S' C4S' H4SC 110.6 . . ?
O1S C4S' H4SC 110.6 . . ?
C3S' C4S' H4SD 110.6 . . ?
O1S C4S' H4SD 110.6 . . ?
H4SC C4S' H4SD 108.7 . . ?
C6S O3S C5S 108.75(15) . . ?
C7S O4S C8S 108.91(12) . . ?
O3S C5S C6S 110.74(17) . 2_566 ?
O3S C5S H5SA 109.5 . . ?
C6S C5S H5SA 109.5 2_566 . ?
O3S C5S H5SB 109.5 . . ?
C6S C5S H5SB 109.5 2_566 . ?
H5SA C5S H5SB 108.1 . . ?
O3S C6S C5S 111.35(17) . 2_566 ?
O3S C6S H6SA 109.4 . . ?
C5S C6S H6SA 109.4 2_566 . ?
O3S C6S H6SB 109.4 . . ?
C5S C6S H6SB 109.4 2_566 . ?
H6SA C6S H6SB 108.0 . . ?
O4S C7S C8S 111.08(13) . 2_777 ?
O4S C7S H7SA 109.4 . . ?
C8S C7S H7SA 109.4 2_777 . ?
O4S C7S H7SB 109.4 . . ?
C8S C7S H7SB 109.4 2_777 . ?
H7SA C7S H7SB 108.0 . . ?
O4S C8S C7S 110.93(13) . 2_777 ?
O4S C8S H8SA 109.5 . . ?
C7S C8S H8SA 109.5 2_777 . ?
O4S C8S H8SB 109.5 . . ?
C7S C8S H8SB 109.5 2_777 . ?
H8SA C8S H8SB 108.0 . . ?
C12S O5S C9S 109.82(13) . . ?
C11S O6S C10S 108.75(13) . . ?
O5S C9S C10S 110.42(14) . . ?
O5S C9S H9SA 109.6 . . ?
C10S C9S H9SA 109.6 . . ?
O5S C9S H9SB 109.6 . . ?
C10S C9S H9SB 109.6 . . ?
H9SA C9S H9SB 108.1 . . ?
O6S C10S C9S 110.51(14) . . ?
O6S C10S H10C 109.5 . . ?
C9S C10S H10C 109.5 . . ?
O6S C10S H10D 109.5 . . ?
C9S C10S H10D 109.5 . . ?
H10C C10S H10D 108.1 . . ?
O6S C11S C12S 110.77(14) . . ?
O6S C11S H11A 109.5 . . ?
C12S C11S H11A 109.5 . . ?
O6S C11S H11B 109.5 . . ?
C12S C11S H11B 109.5 . . ?
H11A C11S H11B 108.1 . . ?
O5S C12S C11S 110.90(15) . . ?
O5S C12S H12C 109.5 . . ?
C11S C12S H12C 109.5 . . ?
O5S C12S H12D 109.5 . . ?
C11S C12S H12D 109.5 . . ?
H12C C12S H12D 108.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C4 N4 C1 N1 90.74(15) . . . . ?
C4 N4 C1 C5 -142.58(12) . . . . ?
C4 N4 C1 C3 -16.64(15) . . . . ?
C2 N1 C1 N4 -123.88(13) . . . . ?
C2 N1 C1 C5 108.75(13) . . . . ?
C2 N1 C1 C3 -15.98(15) . . . . ?
C1 N1 C2 O1 -172.42(14) . . . . ?
C1 N1 C2 N2 8.30(16) . . . . ?
C3 N2 C2 O1 -174.65(13) . . . . ?
C17 N2 C2 O1 -16.5(2) . . . . ?
C3 N2 C2 N1 4.66(16) . . . . ?
C17 N2 C2 N1 162.81(13) . . . . ?
C2 N2 C3 N3 93.53(14) . . . . ?
C17 N2 C3 N3 -63.77(17) . . . . ?
C2 N2 C3 C11 -138.67(13) . . . . ?
C17 N2 C3 C11 64.03(17) . . . . ?
C2 N2 C3 C1 -13.93(14) . . . . ?
C17 N2 C3 C1 -171.23(12) . . . . ?
C4 N3 C3 N2 -121.29(13) . . . . ?
C18 N3 C3 N2 74.30(17) . . . . ?
C4 N3 C3 C11 110.00(13) . . . . ?
C18 N3 C3 C11 -54.42(18) . . . . ?
C4 N3 C3 C1 -13.08(14) . . . . ?
C18 N3 C3 C1 -177.50(13) . . . . ?
N4 C1 C3 N2 133.36(11) . . . . ?
N1 C1 C3 N2 17.00(13) . . . . ?
C5 C1 C3 N2 -103.72(13) . . . . ?
N4 C1 C3 N3 16.80(13) . . . . ?
N1 C1 C3 N3 -99.57(11) . . . . ?
C5 C1 C3 N3 139.72(12) . . . . ?
N4 C1 C3 C11 -103.44(13) . . . . ?
N1 C1 C3 C11 140.19(12) . . . . ?
C5 C1 C3 C11 19.48(17) . . . . ?
C1 N4 C4 O2 -172.65(14) . . . . ?
C1 N4 C4 N3 9.29(16) . . . . ?
C18 N3 C4 O2 -9.4(2) . . . . ?
C3 N3 C4 O2 -174.50(13) . . . . ?
C18 N3 C4 N4 168.67(13) . . . . ?
C3 N3 C4 N4 3.60(16) . . . . ?
N4 C1 C5 C10 20.64(19) . . . . ?
N1 C1 C5 C10 148.22(13) . . . . ?
C3 C1 C5 C10 -96.61(16) . . . . ?
N4 C1 C5 C6 -157.79(13) . . . . ?
N1 C1 C5 C6 -30.22(18) . . . . ?
C3 C1 C5 C6 84.96(16) . . . . ?
C10 C5 C6 C7 -1.0(2) . . . . ?
C1 C5 C6 C7 177.50(14) . . . . ?
C5 C6 C7 C8 -0.7(2) . . . . ?
C6 C7 C8 C9 1.7(2) . . . . ?
C7 C8 C9 C10 -1.0(2) . . . . ?
C8 C9 C10 C5 -0.6(2) . . . . ?
C6 C5 C10 C9 1.6(2) . . . . ?
C1 C5 C10 C9 -176.84(14) . . . . ?
N2 C3 C11 C12 14.81(19) . . . . ?
N3 C3 C11 C12 143.40(14) . . . . ?
C1 C3 C11 C12 -102.30(15) . . . . ?
N2 C3 C11 C16 -167.00(13) . . . . ?
N3 C3 C11 C16 -38.40(18) . . . . ?
C1 C3 C11 C16 75.90(17) . . . . ?
C16 C11 C12 C13 2.3(2) . . . . ?
C3 C11 C12 C13 -179.44(13) . . . . ?
C11 C12 C13 C14 -1.4(2) . . . . ?
C12 C13 C14 C15 -0.5(2) . . . . ?
C13 C14 C15 C16 1.5(2) . . . . ?
C14 C15 C16 C11 -0.5(2) . . . . ?
C12 C11 C16 C15 -1.4(2) . . . . ?
C3 C11 C16 C15 -179.62(14) . . . . ?
C2A N1A C1A N4A -92.45(14) . . . . ?
C2A N1A C1A C5A 140.66(12) . . . . ?
C2A N1A C1A C3A 14.94(15) . . . . ?
C4A N4A C1A N1A 121.56(13) . . . . ?
C4A N4A C1A C5A -111.54(13) . . . . ?
C4A N4A C1A C3A 13.73(15) . . . . ?
C1A N1A C2A O1A 172.87(13) . . . . ?
C1A N1A C2A N2A -9.23(16) . . . . ?
C17A N2A C2A O1A 3.4(2) . . . . ?
C3A N2A C2A O1A 176.12(13) . . . . ?
C17A N2A C2A N1A -174.49(12) . . . . ?
C3A N2A C2A N1A -1.82(16) . . . . ?
C4A N3A C3A N2A -95.25(14) . . . . ?
C18A N3A C3A N2A 62.49(17) . . . . ?
C4A N3A C3A C11A 137.22(13) . . . . ?
C18A N3A C3A C11A -65.04(18) . . . . ?
C4A N3A C3A C1A 13.02(15) . . . . ?
C18A N3A C3A C1A 170.76(13) . . . . ?
C2A N2A C3A N3A 119.37(13) . . . . ?
C17A N2A C3A N3A -68.16(17) . . . . ?
C2A N2A C3A C11A -112.65(13) . . . . ?
C17A N2A C3A C11A 59.82(17) . . . . ?
C2A N2A C3A C1A 10.46(14) . . . . ?
C17A N2A C3A C1A -177.07(12) . . . . ?
N1A C1A C3A N3A -131.71(11) . . . . ?
N4A C1A C3A N3A -15.19(13) . . . . ?
C5A C1A C3A N3A 106.28(13) . . . . ?
N1A C1A C3A N2A -14.34(13) . . . . ?
N4A C1A C3A N2A 102.17(11) . . . . ?
C5A C1A C3A N2A -136.36(12) . . . . ?
N1A C1A C3A C11A 106.10(13) . . . . ?
N4A C1A C3A C11A -137.38(12) . . . . ?
C5A C1A C3A C11A -15.91(18) . . . . ?
C1A N4A C4A O2A 173.29(14) . . . . ?
C1A N4A C4A N3A -6.50(16) . . . . ?
C3A N3A C4A O2A 175.11(13) . . . . ?
C18A N3A C4A O2A 16.6(2) . . . . ?
C3A N3A C4A N4A -5.09(16) . . . . ?
C18A N3A C4A N4A -163.64(13) . . . . ?
N1A C1A C5A C6A -21.53(19) . . . . ?
N4A C1A C5A C6A -149.14(13) . . . . ?
C3A C1A C5A C6A 95.14(16) . . . . ?
N1A C1A C5A C10A 156.83(13) . . . . ?
N4A C1A C5A C10A 29.22(18) . . . . ?
C3A C1A C5A C10A -86.50(16) . . . . ?
C10A C5A C6A C7A -1.5(2) . . . . ?
C1A C5A C6A C7A 176.91(14) . . . . ?
C5A C6A C7A C8A 0.3(2) . . . . ?
C6A C7A C8A C9A 1.1(2) . . . . ?
C7A C8A C9A C10A -1.3(2) . . . . ?
C8A C9A C10A C5A 0.1(2) . . . . ?
C6A C5A C10A C9A 1.3(2) . . . . ?
C1A C5A C10A C9A -177.12(13) . . . . ?
N3A C3A C11A C16A -21.94(19) . . . . ?
N2A C3A C11A C16A -150.55(13) . . . . ?
C1A C3A C11A C16A 94.73(16) . . . . ?
N3A C3A C11A C12A 160.31(13) . . . . ?
N2A C3A C11A C12A 31.70(18) . . . . ?
C1A C3A C11A C12A -83.02(17) . . . . ?
C16A C11A C12A C13A 0.9(2) . . . . ?
C3A C11A C12A C13A 178.65(14) . . . . ?
C11A C12A C13A C14A 0.2(2) . . . . ?
C12A C13A C14A C15A -0.4(2) . . . . ?
C13A C14A C15A C16A -0.4(3) . . . . ?
C14A C15A C16A C11A 1.5(3) . . . . ?
C12A C11A C16A C15A -1.7(2) . . . . ?
C3A C11A C16A C15A -179.45(14) . . . . ?
C4S O1S C1S C2S 57.1(6) . . . . ?
C3S O2S C2S C1S 65.1(5) . . . . ?
O1S C1S C2S O2S -60.7(5) . . . . ?
C2S O2S C3S C4S -64.1(6) . . . . ?
C1S O1S C4S C3S -57.3(9) . . . . ?
O2S C3S C4S O1S 61.0(10) . . . . ?
C4S' O1S C1S' C2S' -66.3(9) . . . . ?
O1S C1S' C2S' O2S 68.2(5) . . . . ?
C3S' O2S C2S' C1S' -64.7(5) . . . . ?
C2S' O2S C3S' C4S' 64.1(9) . . . . ?
O2S C3S' C4S' O1S -64.9(11) . . . . ?
C1S' O1S C4S' C3S' 66.0(11) . . . . ?
C6S O3S C5S C6S 57.3(2) . . . 2_566 ?
C5S O3S C6S C5S -57.7(2) . . . 2_566 ?
C8S O4S C7S C8S 57.54(18) . . . 2_777 ?
C7S O4S C8S C7S -57.45(18) . . . 2_777 ?
C12S O5S C9S C10S -57.02(19) . . . . ?
C11S O6S C10S C9S -59.84(18) . . . . ?
O5S C9S C10S O6S 59.68(19) . . . . ?
C10S O6S C11S C12S 58.69(18) . . . . ?
C9S O5S C12S C11S 56.02(19) . . . . ?
O6S C11S C12S O5S -57.7(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
N1 H1N O2A 0.873(19) 2.001(19) 2.8659(17) 170.9(17) .
N4A H4NA O1 0.92(2) 1.96(2) 2.8753(16) 170.2(17) .
N4 H4N O1A 0.873(18) 1.952(19) 2.8117(16) 168.0(17) 1_655
N1A H1NA O2 0.909(18) 1.938(18) 2.8381(16) 169.8(16) 1_455

_refine_diff_density_max         0.381
_refine_diff_density_min         -0.243
_refine_diff_density_rms         0.050



####################################################################### 
# 
# 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_1a-MeLactate
_database_code_depnum_ccdc_archive 'CCDC 2072841'
loop_
_audit_author_name
_audit_author_address
'Valentina Karnoukhova'
;A N Nesmeyanov Institute of Organoelement Compounds of Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2021-03-24 deposited with the CCDC.	2021-05-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H18 N4 O2, C4 H8 O3'
_chemical_formula_sum            'C22 H26 N4 O5'
_chemical_formula_weight         426.47
_chemical_absolute_configuration .

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   10.8660(5)
_cell_length_b                   12.6977(6)
_cell_length_c                   15.5356(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2143.50(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    446
_cell_measurement_theta_min      3
_cell_measurement_theta_max      25

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.322
_exptl_crystal_F_000             904
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.210
_exptl_absorpt_coefficient_mu    0.095
_shelx_estimated_absorpt_T_min   0.970
_shelx_estimated_absorpt_T_max   0.980
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7134
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   'Bruker SADABS'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker SMART APEX II diffractometer'
_diffrn_detector_type            'Bruker APEX II CCD area detector'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            27874
_diffrn_reflns_av_unetI/netI     0.0204
_diffrn_reflns_av_R_equivalents  0.0253
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.071
_diffrn_reflns_theta_max         29.989
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             6254
_reflns_number_gt                5690
_reflns_threshold_expression     I>2σ(I)
_reflns_Friedel_coverage         0.785
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

_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.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015b)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0578P)²+0.3325P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6254
_refine_ls_number_parameters     296
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0405
_refine_ls_R_factor_gt           0.0353
_refine_ls_wR_factor_ref         0.0989
_refine_ls_wR_factor_gt          0.0936
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_restrained_S_all      1.014
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 -0.01501(10) 0.38637(10) -0.03498(8) 0.0229(2) Uani 1 1 d . . . . .
O2 O 0.52513(10) 0.39006(10) -0.02611(8) 0.0222(2) Uani 1 1 d . . . . .
N1 N 0.13820(13) 0.30777(11) 0.04600(10) 0.0224(3) Uani 1 1 d . . . . .
H1N H 0.107(2) 0.244(2) 0.0430(16) 0.034(6) Uiso 1 1 d . . . . .
N2 N 0.14371(13) 0.47960(11) 0.02560(9) 0.0208(3) Uani 1 1 d . . . . .
N3 N 0.36692(12) 0.48238(11) 0.03694(9) 0.0202(3) Uani 1 1 d . . . . .
N4 N 0.36034(13) 0.30816(11) 0.04013(9) 0.0200(3) Uani 1 1 d . . . . .
H4N H 0.394(2) 0.246(2) 0.0416(15) 0.027(5) Uiso 1 1 d . . . . .
C1 C 0.25159(15) 0.33605(11) 0.08919(9) 0.0165(2) Uani 1 1 d . . . . .
C2 C 0.08095(14) 0.39019(13) 0.00796(9) 0.0184(3) Uani 1 1 d . . . . .
C3 C 0.25062(15) 0.46254(10) 0.08040(9) 0.0162(2) Uani 1 1 d . . . . .
C4 C 0.42633(14) 0.39267(13) 0.01332(9) 0.0181(3) Uani 1 1 d . . . . .
C5 C 0.25812(16) 0.29251(11) 0.18046(9) 0.0186(3) Uani 1 1 d . . . . .
C6 C 0.15321(17) 0.25753(14) 0.22286(12) 0.0266(3) Uani 1 1 d . . . . .
H6A H 0.075437 0.260715 0.195048 0.032 Uiso 1 1 calc R U . . .
C7 C 0.1622(2) 0.21771(15) 0.30633(13) 0.0348(4) Uani 1 1 d . . . . .
H7A H 0.090445 0.192845 0.334755 0.042 Uiso 1 1 calc R U . . .
C8 C 0.2742(2) 0.21409(14) 0.34795(12) 0.0352(5) Uani 1 1 d . . . . .
H8A H 0.279549 0.186862 0.404787 0.042 Uiso 1 1 calc R U . . .
C9 C 0.3787(2) 0.25029(16) 0.30660(12) 0.0334(4) Uani 1 1 d . . . . .
H9A H 0.455815 0.248732 0.335325 0.040 Uiso 1 1 calc R U . . .
C10 C 0.37090(16) 0.28898(14) 0.22297(11) 0.0257(3) Uani 1 1 d . . . . .
H10A H 0.443060 0.313171 0.194670 0.031 Uiso 1 1 calc R U . . .
C11 C 0.24048(15) 0.52175(11) 0.16497(9) 0.0172(3) Uani 1 1 d . . . . .
C12 C 0.12567(15) 0.53376(13) 0.20392(11) 0.0222(3) Uani 1 1 d . . . . .
H12A H 0.053959 0.507657 0.176195 0.027 Uiso 1 1 calc R U . . .
C13 C 0.11594(18) 0.58375(14) 0.28309(12) 0.0291(4) Uani 1 1 d . . . . .
H13A H 0.037763 0.590781 0.309861 0.035 Uiso 1 1 calc R U . . .
C14 C 0.2201(2) 0.62343(15) 0.32317(11) 0.0317(4) Uani 1 1 d . . . . .
H14A H 0.212772 0.659955 0.376292 0.038 Uiso 1 1 calc R U . . .
C15 C 0.33475(19) 0.60988(15) 0.28582(11) 0.0297(4) Uani 1 1 d . . . . .
H15A H 0.406300 0.635569 0.313989 0.036 Uiso 1 1 calc R U . . .
C16 C 0.34504(15) 0.55845(14) 0.20676(10) 0.0226(3) Uani 1 1 d . . . . .
H16A H 0.423783 0.548507 0.181455 0.027 Uiso 1 1 calc R U . . .
C17 C 0.10278(19) 0.58207(14) -0.00434(14) 0.0343(4) Uani 1 1 d . . . . .
H17A H 0.014025 0.589038 0.005319 0.051 Uiso 1 1 calc R U . . .
H17B H 0.120352 0.588957 -0.065959 0.051 Uiso 1 1 calc R U . . .
H17C H 0.146321 0.637393 0.027390 0.051 Uiso 1 1 calc R U . . .
C18 C 0.40618(18) 0.58411(14) 0.00475(13) 0.0312(4) Uani 1 1 d . . . . .
H18A H 0.496287 0.587452 0.004633 0.047 Uiso 1 1 calc R U . . .
H18B H 0.373363 0.639830 0.041870 0.047 Uiso 1 1 calc R U . . .
H18C H 0.375441 0.593818 -0.054020 0.047 Uiso 1 1 calc R U . . .
O1S O 0.10425(14) 0.04453(17) 0.74211(12) 0.0524(5) Uani 1 1 d . . . . .
O2S O 0.29401(13) 0.06889(13) 0.79410(9) 0.0352(3) Uani 1 1 d . . . . .
O3S O 0.18595(15) 0.06079(15) 0.57600(10) 0.0444(4) Uani 1 1 d . . . . .
H3S H 0.141(4) 0.003(3) 0.589(3) 0.097(13) Uiso 1 1 d . . . . .
C1S C 0.21172(16) 0.05772(15) 0.73065(12) 0.0282(4) Uani 1 1 d . . . . .
C2S C 0.27280(16) 0.06594(15) 0.64309(11) 0.0273(3) Uani 1 1 d . . . . .
H2SA H 0.334213 0.007877 0.636334 0.033 Uiso 1 1 calc R U . . .
C3S C 0.3372(2) 0.17153(17) 0.63509(13) 0.0358(4) Uani 1 1 d . . . . .
H3SA H 0.366869 0.180681 0.576006 0.054 Uiso 1 1 calc R U . . .
H3SB H 0.406978 0.174002 0.674972 0.054 Uiso 1 1 calc R U . . .
H3SC H 0.279195 0.228110 0.649136 0.054 Uiso 1 1 calc R U . . .
C4S C 0.2437(3) 0.07143(19) 0.88054(13) 0.0494(6) Uani 1 1 d . . . . .
H4SA H 0.311133 0.072020 0.922434 0.074 Uiso 1 1 calc R U . . .
H4SB H 0.192394 0.008994 0.889870 0.074 Uiso 1 1 calc R U . . .
H4SC H 0.193596 0.134996 0.887742 0.074 Uiso 1 1 calc R U . . .


_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 C2 1.2388(18) . ?
O2 C4 1.2365(18) . ?
N1 C2 1.353(2) . ?
N1 C1 1.448(2) . ?
N1 H1N 0.89(3) . ?
N2 C2 1.352(2) . ?
N2 C17 1.452(2) . ?
N2 C3 1.4564(19) . ?
N3 C4 1.360(2) . ?
N3 C18 1.449(2) . ?
N3 C3 1.455(2) . ?
N4 C4 1.356(2) . ?
N4 C1 1.450(2) . ?
N4 H4N 0.88(3) . ?
C1 C5 1.5235(19) . ?
C1 C3 1.6120(19) . ?
C3 C11 1.5177(19) . ?
C5 C6 1.390(2) . ?
C5 C10 1.393(2) . ?
C6 C7 1.395(3) . ?
C6 H6A 0.9500 . ?
C7 C8 1.379(3) . ?
C7 H7A 0.9500 . ?
C8 C9 1.383(3) . ?
C8 H8A 0.9500 . ?
C9 C10 1.392(3) . ?
C9 H9A 0.9500 . ?
C10 H10A 0.9500 . ?
C11 C16 1.389(2) . ?
C11 C12 1.395(2) . ?
C12 C13 1.388(2) . ?
C12 H12A 0.9500 . ?
C13 C14 1.386(3) . ?
C13 H13A 0.9500 . ?
C14 C15 1.385(3) . ?
C14 H14A 0.9500 . ?
C15 C16 1.395(2) . ?
C15 H15A 0.9500 . ?
C16 H16A 0.9500 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
O1S C1S 1.193(2) . ?
O2S C1S 1.338(2) . ?
O2S C4S 1.450(2) . ?
O3S C2S 1.408(2) . ?
O3S H3S 0.91(4) . ?
C1S C2S 1.517(3) . ?
C2S C3S 1.517(3) . ?
C2S H2SA 1.0000 . ?
C3S H3SA 0.9800 . ?
C3S H3SB 0.9800 . ?
C3S H3SC 0.9800 . ?
C4S H4SA 0.9800 . ?
C4S H4SB 0.9800 . ?
C4S H4SC 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
C2 N1 C1 113.68(13) . . ?
C2 N1 H1N 120.7(15) . . ?
C1 N1 H1N 125.7(15) . . ?
C2 N2 C17 122.21(13) . . ?
C2 N2 C3 113.32(13) . . ?
C17 N2 C3 124.41(13) . . ?
C4 N3 C18 120.92(13) . . ?
C4 N3 C3 113.12(13) . . ?
C18 N3 C3 124.76(13) . . ?
C4 N4 C1 113.52(13) . . ?
C4 N4 H4N 120.1(15) . . ?
C1 N4 H4N 123.5(15) . . ?
N1 C1 N4 112.90(12) . . ?
N1 C1 C5 112.39(13) . . ?
N4 C1 C5 111.26(13) . . ?
N1 C1 C3 101.67(12) . . ?
N4 C1 C3 101.78(12) . . ?
C5 C1 C3 116.15(11) . . ?
O1 C2 N2 124.50(15) . . ?
O1 C2 N1 126.28(15) . . ?
N2 C2 N1 109.20(13) . . ?
N3 C3 N2 113.32(11) . . ?
N3 C3 C11 112.27(12) . . ?
N2 C3 C11 111.99(12) . . ?
N3 C3 C1 101.90(12) . . ?
N2 C3 C1 101.71(12) . . ?
C11 C3 C1 114.88(11) . . ?
O2 C4 N4 126.16(15) . . ?
O2 C4 N3 124.63(15) . . ?
N4 C4 N3 109.21(13) . . ?
C6 C5 C10 119.12(14) . . ?
C6 C5 C1 121.27(15) . . ?
C10 C5 C1 119.60(15) . . ?
C5 C6 C7 119.94(17) . . ?
C5 C6 H6A 120.0 . . ?
C7 C6 H6A 120.0 . . ?
C8 C7 C6 120.65(18) . . ?
C8 C7 H7A 119.7 . . ?
C6 C7 H7A 119.7 . . ?
C7 C8 C9 119.70(16) . . ?
C7 C8 H8A 120.1 . . ?
C9 C8 H8A 120.1 . . ?
C8 C9 C10 120.09(18) . . ?
C8 C9 H9A 120.0 . . ?
C10 C9 H9A 120.0 . . ?
C9 C10 C5 120.49(17) . . ?
C9 C10 H10A 119.8 . . ?
C5 C10 H10A 119.8 . . ?
C16 C11 C12 119.48(14) . . ?
C16 C11 C3 120.76(14) . . ?
C12 C11 C3 119.64(14) . . ?
C13 C12 C11 120.17(16) . . ?
C13 C12 H12A 119.9 . . ?
C11 C12 H12A 119.9 . . ?
C14 C13 C12 120.13(16) . . ?
C14 C13 H13A 119.9 . . ?
C12 C13 H13A 119.9 . . ?
C15 C14 C13 120.06(15) . . ?
C15 C14 H14A 120.0 . . ?
C13 C14 H14A 120.0 . . ?
C14 C15 C16 119.93(16) . . ?
C14 C15 H15A 120.0 . . ?
C16 C15 H15A 120.0 . . ?
C11 C16 C15 120.18(16) . . ?
C11 C16 H16A 119.9 . . ?
C15 C16 H16A 119.9 . . ?
N2 C17 H17A 109.5 . . ?
N2 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
N2 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N3 C18 H18A 109.5 . . ?
N3 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N3 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C1S O2S C4S 115.63(17) . . ?
C2S O3S H3S 104(3) . . ?
O1S C1S O2S 123.98(19) . . ?
O1S C1S C2S 124.87(18) . . ?
O2S C1S C2S 111.15(15) . . ?
O3S C2S C1S 111.56(15) . . ?
O3S C2S C3S 106.83(17) . . ?
C1S C2S C3S 109.63(15) . . ?
O3S C2S H2SA 109.6 . . ?
C1S C2S H2SA 109.6 . . ?
C3S C2S H2SA 109.6 . . ?
C2S C3S H3SA 109.5 . . ?
C2S C3S H3SB 109.5 . . ?
H3SA C3S H3SB 109.5 . . ?
C2S C3S H3SC 109.5 . . ?
H3SA C3S H3SC 109.5 . . ?
H3SB C3S H3SC 109.5 . . ?
O2S C4S H4SA 109.5 . . ?
O2S C4S H4SB 109.5 . . ?
H4SA C4S H4SB 109.5 . . ?
O2S C4S H4SC 109.5 . . ?
H4SA C4S H4SC 109.5 . . ?
H4SB C4S H4SC 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
C2 N1 C1 N4 -102.16(16) . . . . ?
C2 N1 C1 C5 130.99(14) . . . . ?
C2 N1 C1 C3 6.12(17) . . . . ?
C4 N4 C1 N1 114.36(14) . . . . ?
C4 N4 C1 C5 -118.19(14) . . . . ?
C4 N4 C1 C3 6.16(16) . . . . ?
C17 N2 C2 O1 0.5(3) . . . . ?
C3 N2 C2 O1 177.56(14) . . . . ?
C17 N2 C2 N1 -178.17(17) . . . . ?
C3 N2 C2 N1 -1.13(19) . . . . ?
C1 N1 C2 O1 177.75(15) . . . . ?
C1 N1 C2 N2 -3.60(19) . . . . ?
C4 N3 C3 N2 -103.01(15) . . . . ?
C18 N3 C3 N2 64.46(19) . . . . ?
C4 N3 C3 C11 128.88(13) . . . . ?
C18 N3 C3 C11 -63.6(2) . . . . ?
C4 N3 C3 C1 5.46(16) . . . . ?
C18 N3 C3 C1 172.93(15) . . . . ?
C2 N2 C3 N3 113.23(15) . . . . ?
C17 N2 C3 N3 -69.8(2) . . . . ?
C2 N2 C3 C11 -118.52(14) . . . . ?
C17 N2 C3 C11 58.4(2) . . . . ?
C2 N2 C3 C1 4.65(16) . . . . ?
C17 N2 C3 C1 -178.39(17) . . . . ?
N1 C1 C3 N3 -123.24(13) . . . . ?
N4 C1 C3 N3 -6.56(14) . . . . ?
C5 C1 C3 N3 114.44(14) . . . . ?
N1 C1 C3 N2 -6.05(14) . . . . ?
N4 C1 C3 N2 110.63(13) . . . . ?
C5 C1 C3 N2 -128.37(14) . . . . ?
N1 C1 C3 C11 115.12(14) . . . . ?
N4 C1 C3 C11 -128.20(13) . . . . ?
C5 C1 C3 C11 -7.2(2) . . . . ?
C1 N4 C4 O2 176.63(14) . . . . ?
C1 N4 C4 N3 -3.13(18) . . . . ?
C18 N3 C4 O2 10.3(2) . . . . ?
C3 N3 C4 O2 178.28(14) . . . . ?
C18 N3 C4 N4 -169.97(16) . . . . ?
C3 N3 C4 N4 -1.96(18) . . . . ?
N1 C1 C5 C6 -17.1(2) . . . . ?
N4 C1 C5 C6 -144.86(15) . . . . ?
C3 C1 C5 C6 99.35(18) . . . . ?
N1 C1 C5 C10 163.83(14) . . . . ?
N4 C1 C5 C10 36.10(18) . . . . ?
C3 C1 C5 C10 -79.69(18) . . . . ?
C10 C5 C6 C7 -1.2(2) . . . . ?
C1 C5 C6 C7 179.77(15) . . . . ?
C5 C6 C7 C8 1.0(3) . . . . ?
C6 C7 C8 C9 0.0(3) . . . . ?
C7 C8 C9 C10 -0.8(3) . . . . ?
C8 C9 C10 C5 0.6(3) . . . . ?
C6 C5 C10 C9 0.4(2) . . . . ?
C1 C5 C10 C9 179.48(15) . . . . ?
N3 C3 C11 C16 -20.36(19) . . . . ?
N2 C3 C11 C16 -149.17(14) . . . . ?
C1 C3 C11 C16 95.46(18) . . . . ?
N3 C3 C11 C12 163.68(14) . . . . ?
N2 C3 C11 C12 34.86(18) . . . . ?
C1 C3 C11 C12 -80.51(18) . . . . ?
C16 C11 C12 C13 1.2(2) . . . . ?
C3 C11 C12 C13 177.20(14) . . . . ?
C11 C12 C13 C14 1.0(3) . . . . ?
C12 C13 C14 C15 -2.4(3) . . . . ?
C13 C14 C15 C16 1.5(3) . . . . ?
C12 C11 C16 C15 -2.0(2) . . . . ?
C3 C11 C16 C15 -177.99(14) . . . . ?
C14 C15 C16 C11 0.7(3) . . . . ?
C4S O2S C1S O1S -4.1(3) . . . . ?
C4S O2S C1S C2S 174.88(17) . . . . ?
O1S C1S C2S O3S 2.6(3) . . . . ?
O2S C1S C2S O3S -176.35(17) . . . . ?
O1S C1S C2S C3S 120.8(2) . . . . ?
O2S C1S C2S C3S -58.2(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
N1 H1N O2 0.89(3) 1.93(3) 2.8133(19) 173(2) 4_455
N4 H4N O1 0.88(3) 1.95(3) 2.8182(18) 173(2) 4
O3S H3S O1 0.91(4) 2.18(4) 2.960(2) 143(4) 3_545

_refine_diff_density_max         0.309
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.040



####################################################################### 
# 
# 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_1a
_database_code_depnum_ccdc_archive 'CCDC 2072843'
loop_
_audit_author_name
_audit_author_address
'Valentina Karnoukhova'
;A N Nesmeyanov Institute of Organoelement Compounds of Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2021-03-24 deposited with the CCDC.	2021-05-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H18 N4 O2'
_chemical_formula_sum            'C18 H18 N4 O2'
_chemical_formula_weight         322.36

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   15.1775(15)
_cell_length_b                   11.3912(11)
_cell_length_c                   9.0508(9)
_cell_angle_alpha                90
_cell_angle_beta                 99.279(2)
_cell_angle_gamma                90
_cell_volume                     1544.3(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    396
_cell_measurement_theta_min      3
_cell_measurement_theta_max      25

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.386
_exptl_crystal_F_000             680
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    0.094
_shelx_estimated_absorpt_T_min   0.977
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6699
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX DUO diffractometer'
_diffrn_detector_type            'Bruker APEX II CCD area detector'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20184
_diffrn_reflns_av_unetI/netI     0.0480
_diffrn_reflns_av_R_equivalents  0.0572
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.246
_diffrn_reflns_theta_max         30.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4509
_reflns_number_gt                3354
_reflns_threshold_expression     I>2σ(I)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015b)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0539P)²+0.5114P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4509
_refine_ls_number_parameters     227
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0690
_refine_ls_R_factor_gt           0.0478
_refine_ls_wR_factor_ref         0.1224
_refine_ls_wR_factor_gt          0.1104
_refine_ls_goodness_of_fit_ref   1.019
_refine_ls_restrained_S_all      1.019
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.10951(7) 0.29144(9) 1.09347(11) 0.0180(2) Uani 1 1 d . . . . .
O2 O -0.00466(7) 0.62132(9) 0.62136(11) 0.0187(2) Uani 1 1 d . . . . .
N1 N 0.15593(8) 0.32364(10) 0.86606(13) 0.0148(2) Uani 1 1 d . . . . .
H1N H 0.1356(12) 0.2597(18) 0.824(2) 0.027(5) Uiso 1 1 d . . . . .
N2 N 0.13945(8) 0.47538(10) 1.01265(13) 0.0144(2) Uani 1 1 d . . . . .
N3 N 0.11662(8) 0.61740(10) 0.81013(13) 0.0149(2) Uani 1 1 d . . . . .
N4 N 0.08203(8) 0.45585(10) 0.67642(13) 0.0150(2) Uani 1 1 d . . . . .
H4N H 0.0639(12) 0.4220(16) 0.594(2) 0.020(4) Uiso 1 1 d . . . . .
C1 C 0.16460(9) 0.42404(12) 0.77168(14) 0.0129(3) Uani 1 1 d . . . . .
C2 C 0.13188(9) 0.35621(12) 0.99935(15) 0.0137(3) Uani 1 1 d . . . . .
C3 C 0.17478(9) 0.52912(11) 0.88882(15) 0.0130(3) Uani 1 1 d . . . . .
C4 C 0.05795(9) 0.56903(12) 0.69477(15) 0.0148(3) Uani 1 1 d . . . . .
C5 C 0.24159(9) 0.41125(12) 0.68487(15) 0.0146(3) Uani 1 1 d . . . . .
C6 C 0.30965(10) 0.33142(14) 0.72901(17) 0.0206(3) Uani 1 1 d . . . . .
H6A H 0.307258 0.281641 0.812481 0.025 Uiso 1 1 calc R U . . .
C7 C 0.38132(10) 0.32398(15) 0.65158(19) 0.0266(3) Uani 1 1 d . . . . .
H7A H 0.427234 0.268149 0.681433 0.032 Uiso 1 1 calc R U . . .
C8 C 0.38640(11) 0.39692(15) 0.53180(19) 0.0270(4) Uani 1 1 d . . . . .
H8A H 0.436133 0.392498 0.480349 0.032 Uiso 1 1 calc R U . . .
C9 C 0.31871(11) 0.47648(15) 0.48706(19) 0.0268(3) Uani 1 1 d . . . . .
H9A H 0.321733 0.527031 0.404538 0.032 Uiso 1 1 calc R U . . .
C10 C 0.24631(11) 0.48253(14) 0.56270(17) 0.0226(3) Uani 1 1 d . . . . .
H10A H 0.199359 0.536334 0.530174 0.027 Uiso 1 1 calc R U . . .
C11 C 0.26924(9) 0.57375(12) 0.93635(15) 0.0150(3) Uani 1 1 d . . . . .
C12 C 0.32490(10) 0.52042(13) 1.05481(16) 0.0186(3) Uani 1 1 d . . . . .
H12A H 0.302790 0.458222 1.108418 0.022 Uiso 1 1 calc R U . . .
C13 C 0.41237(10) 0.55773(15) 1.09477(18) 0.0243(3) Uani 1 1 d . . . . .
H13A H 0.449964 0.521031 1.175731 0.029 Uiso 1 1 calc R U . . .
C14 C 0.44518(10) 0.64800(15) 1.01751(19) 0.0263(3) Uani 1 1 d . . . . .
H14A H 0.505105 0.673647 1.045478 0.032 Uiso 1 1 calc R U . . .
C15 C 0.39046(10) 0.70088(14) 0.89932(19) 0.0255(3) Uani 1 1 d . . . . .
H15A H 0.412950 0.762766 0.845684 0.031 Uiso 1 1 calc R U . . .
C16 C 0.30296(10) 0.66395(13) 0.85882(17) 0.0199(3) Uani 1 1 d . . . . .
H16A H 0.265751 0.700630 0.777385 0.024 Uiso 1 1 calc R U . . .
C17 C 0.12869(11) 0.53451(13) 1.15022(17) 0.0214(3) Uani 1 1 d . . . . .
H17A H 0.137738 0.478228 1.233187 0.032 Uiso 1 1 calc R U . . .
H17B H 0.068379 0.567442 1.140404 0.032 Uiso 1 1 calc R U . . .
H17C H 0.172678 0.597869 1.170201 0.032 Uiso 1 1 calc R U . . .
C18 C 0.09516(10) 0.72633(12) 0.88032(17) 0.0190(3) Uani 1 1 d . . . . .
H18A H 0.059266 0.776360 0.805581 0.028 Uiso 1 1 calc R U . . .
H18B H 0.150491 0.767219 0.921560 0.028 Uiso 1 1 calc R U . . .
H18C H 0.061273 0.708788 0.961108 0.028 Uiso 1 1 calc R U . . .


_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 C2 1.2160(16) . ?
O2 C4 1.2230(16) . ?
N1 C2 1.3668(18) . ?
N1 C1 1.4461(17) . ?
N1 H1N 0.86(2) . ?
N2 C2 1.3660(17) . ?
N2 C17 1.4479(18) . ?
N2 C3 1.4533(17) . ?
N3 C4 1.3736(18) . ?
N3 C3 1.4474(17) . ?
N3 C18 1.4546(18) . ?
N4 C4 1.3576(18) . ?
N4 C1 1.4479(17) . ?
N4 H4N 0.849(19) . ?
C1 C5 1.5167(19) . ?
C1 C3 1.5899(18) . ?
C3 C11 1.5166(19) . ?
C5 C10 1.383(2) . ?
C5 C6 1.386(2) . ?
C6 C7 1.388(2) . ?
C6 H6A 0.9500 . ?
C7 C8 1.378(2) . ?
C7 H7A 0.9500 . ?
C8 C9 1.381(2) . ?
C8 H8A 0.9500 . ?
C9 C10 1.387(2) . ?
C9 H9A 0.9500 . ?
C10 H10A 0.9500 . ?
C11 C16 1.388(2) . ?
C11 C12 1.393(2) . ?
C12 C13 1.385(2) . ?
C12 H12A 0.9500 . ?
C13 C14 1.381(2) . ?
C13 H13A 0.9500 . ?
C14 C15 1.382(2) . ?
C14 H14A 0.9500 . ?
C15 C16 1.385(2) . ?
C15 H15A 0.9500 . ?
C16 H16A 0.9500 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 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
C2 N1 C1 111.68(11) . . ?
C2 N1 H1N 119.7(13) . . ?
C1 N1 H1N 118.0(13) . . ?
C2 N2 C17 121.23(12) . . ?
C2 N2 C3 112.76(11) . . ?
C17 N2 C3 125.03(11) . . ?
C4 N3 C3 111.37(11) . . ?
C4 N3 C18 120.71(12) . . ?
C3 N3 C18 122.65(11) . . ?
C4 N4 C1 112.90(11) . . ?
C4 N4 H4N 119.0(12) . . ?
C1 N4 H4N 122.6(12) . . ?
N1 C1 N4 113.41(11) . . ?
N1 C1 C5 112.41(11) . . ?
N4 C1 C5 112.37(11) . . ?
N1 C1 C3 102.11(10) . . ?
N4 C1 C3 100.98(10) . . ?
C5 C1 C3 114.68(11) . . ?
O1 C2 N2 124.77(13) . . ?
O1 C2 N1 126.73(13) . . ?
N2 C2 N1 108.47(12) . . ?
N3 C3 N2 113.61(11) . . ?
N3 C3 C11 112.35(11) . . ?
N2 C3 C11 111.83(11) . . ?
N3 C3 C1 102.06(10) . . ?
N2 C3 C1 100.89(10) . . ?
C11 C3 C1 115.30(11) . . ?
O2 C4 N4 126.66(13) . . ?
O2 C4 N3 124.70(13) . . ?
N4 C4 N3 108.64(12) . . ?
C10 C5 C6 118.91(13) . . ?
C10 C5 C1 120.10(12) . . ?
C6 C5 C1 120.96(12) . . ?
C5 C6 C7 120.19(14) . . ?
C5 C6 H6A 119.9 . . ?
C7 C6 H6A 119.9 . . ?
C8 C7 C6 120.55(15) . . ?
C8 C7 H7A 119.7 . . ?
C6 C7 H7A 119.7 . . ?
C7 C8 C9 119.55(14) . . ?
C7 C8 H8A 120.2 . . ?
C9 C8 H8A 120.2 . . ?
C8 C9 C10 119.94(15) . . ?
C8 C9 H9A 120.0 . . ?
C10 C9 H9A 120.0 . . ?
C5 C10 C9 120.85(15) . . ?
C5 C10 H10A 119.6 . . ?
C9 C10 H10A 119.6 . . ?
C16 C11 C12 119.00(13) . . ?
C16 C11 C3 120.91(13) . . ?
C12 C11 C3 120.02(12) . . ?
C13 C12 C11 120.26(14) . . ?
C13 C12 H12A 119.9 . . ?
C11 C12 H12A 119.9 . . ?
C14 C13 C12 120.33(15) . . ?
C14 C13 H13A 119.8 . . ?
C12 C13 H13A 119.8 . . ?
C13 C14 C15 119.72(14) . . ?
C13 C14 H14A 120.1 . . ?
C15 C14 H14A 120.1 . . ?
C14 C15 C16 120.22(15) . . ?
C14 C15 H15A 119.9 . . ?
C16 C15 H15A 119.9 . . ?
C15 C16 C11 120.47(14) . . ?
C15 C16 H16A 119.8 . . ?
C11 C16 H16A 119.8 . . ?
N2 C17 H17A 109.5 . . ?
N2 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
N2 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N3 C18 H18A 109.5 . . ?
N3 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N3 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 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
C2 N1 C1 N4 -88.81(14) . . . . ?
C2 N1 C1 C5 142.36(12) . . . . ?
C2 N1 C1 C3 18.96(14) . . . . ?
C4 N4 C1 N1 123.96(13) . . . . ?
C4 N4 C1 C5 -107.18(13) . . . . ?
C4 N4 C1 C3 15.49(14) . . . . ?
C17 N2 C2 O1 5.7(2) . . . . ?
C3 N2 C2 O1 175.00(13) . . . . ?
C17 N2 C2 N1 -172.58(12) . . . . ?
C3 N2 C2 N1 -3.32(16) . . . . ?
C1 N1 C2 O1 170.75(13) . . . . ?
C1 N1 C2 N2 -10.98(15) . . . . ?
C4 N3 C3 N2 -89.78(13) . . . . ?
C18 N3 C3 N2 64.67(16) . . . . ?
C4 N3 C3 C11 142.01(11) . . . . ?
C18 N3 C3 C11 -63.54(16) . . . . ?
C4 N3 C3 C1 17.93(14) . . . . ?
C18 N3 C3 C1 172.38(12) . . . . ?
C2 N2 C3 N3 122.67(12) . . . . ?
C17 N2 C3 N3 -68.55(17) . . . . ?
C2 N2 C3 C11 -108.85(13) . . . . ?
C17 N2 C3 C11 59.93(17) . . . . ?
C2 N2 C3 C1 14.23(14) . . . . ?
C17 N2 C3 C1 -176.99(12) . . . . ?
N1 C1 C3 N3 -136.19(10) . . . . ?
N4 C1 C3 N3 -19.09(12) . . . . ?
C5 C1 C3 N3 101.97(12) . . . . ?
N1 C1 C3 N2 -18.91(12) . . . . ?
N4 C1 C3 N2 98.18(11) . . . . ?
C5 C1 C3 N2 -140.76(11) . . . . ?
N1 C1 C3 C11 101.74(12) . . . . ?
N4 C1 C3 C11 -141.17(11) . . . . ?
C5 C1 C3 C11 -20.11(16) . . . . ?
C1 N4 C4 O2 174.15(13) . . . . ?
C1 N4 C4 N3 -5.21(15) . . . . ?
C3 N3 C4 O2 171.42(13) . . . . ?
C18 N3 C4 O2 16.4(2) . . . . ?
C3 N3 C4 N4 -9.21(15) . . . . ?
C18 N3 C4 N4 -164.22(12) . . . . ?
N1 C1 C5 C10 163.48(13) . . . . ?
N4 C1 C5 C10 34.11(18) . . . . ?
C3 C1 C5 C10 -80.46(16) . . . . ?
N1 C1 C5 C6 -18.74(18) . . . . ?
N4 C1 C5 C6 -148.12(13) . . . . ?
C3 C1 C5 C6 97.31(15) . . . . ?
C10 C5 C6 C7 0.2(2) . . . . ?
C1 C5 C6 C7 -177.57(14) . . . . ?
C5 C6 C7 C8 1.1(2) . . . . ?
C6 C7 C8 C9 -1.2(3) . . . . ?
C7 C8 C9 C10 0.0(3) . . . . ?
C6 C5 C10 C9 -1.4(2) . . . . ?
C1 C5 C10 C9 176.44(14) . . . . ?
C8 C9 C10 C5 1.3(2) . . . . ?
N3 C3 C11 C16 -26.01(18) . . . . ?
N2 C3 C11 C16 -155.16(13) . . . . ?
C1 C3 C11 C16 90.36(16) . . . . ?
N3 C3 C11 C12 157.08(12) . . . . ?
N2 C3 C11 C12 27.94(17) . . . . ?
C1 C3 C11 C12 -86.55(15) . . . . ?
C16 C11 C12 C13 0.4(2) . . . . ?
C3 C11 C12 C13 177.38(13) . . . . ?
C11 C12 C13 C14 -0.1(2) . . . . ?
C12 C13 C14 C15 -0.3(2) . . . . ?
C13 C14 C15 C16 0.3(2) . . . . ?
C14 C15 C16 C11 0.1(2) . . . . ?
C12 C11 C16 C15 -0.4(2) . . . . ?
C3 C11 C16 C15 -177.36(14) . . . . ?

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
N1 H1N O1 0.86(2) 2.14(2) 2.7823(15) 131.5(17) 4_565
N4 H4N O1 0.849(19) 2.528(18) 2.9620(16) 112.8(14) 4_565
N1 H1N O2 0.86(2) 2.645(19) 3.2680(16) 130.6(16) 2_546
N4 H4N O2 0.849(19) 2.066(19) 2.8974(16) 165.9(17) 3_566

_refine_diff_density_max         0.440
_refine_diff_density_min         -0.238
_refine_diff_density_rms         0.054



####################################################################### 
# 
# 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_1b-HCOOH
_database_code_depnum_ccdc_archive 'CCDC 2072847'
loop_
_audit_author_name
_audit_author_address
'Valentina Karnoukhova'
;A N Nesmeyanov Institute of Organoelement Compounds of Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2021-03-24 deposited with the CCDC.	2021-05-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H22 N4 O2, C H2 O2'
_chemical_formula_sum            'C21 H24 N4 O4'
_chemical_formula_weight         396.44

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.9850(4)
_cell_length_b                   23.1322(11)
_cell_length_c                   9.9624(5)
_cell_angle_alpha                90
_cell_angle_beta                 109.7820(10)
_cell_angle_gamma                90
_cell_volume                     1948.42(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    430
_cell_measurement_theta_min      3
_cell_measurement_theta_max      25

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_F_000             840
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.095
_shelx_estimated_absorpt_T_min   0.977
_shelx_estimated_absorpt_T_max   0.981
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6822
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker SMART APEX II diffractometer'
_diffrn_detector_type            'Bruker APEX II CCD area detector'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            16615
_diffrn_reflns_av_unetI/netI     0.0453
_diffrn_reflns_av_R_equivalents  0.0353
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.761
_diffrn_reflns_theta_max         29.991
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5602
_reflns_number_gt                4269
_reflns_threshold_expression     I>2σ(I)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015b)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0483P)²+0.5885P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5602
_refine_ls_number_parameters     276
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0698
_refine_ls_R_factor_gt           0.0483
_refine_ls_wR_factor_ref         0.1153
_refine_ls_wR_factor_gt          0.1026
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.08060(11) 0.10329(4) -0.05866(10) 0.0194(2) Uani 1 1 d . . . . .
O2 O 0.32102(12) 0.22766(4) 0.44323(11) 0.0203(2) Uani 1 1 d . . . . .
N1 N 0.31935(13) 0.15262(5) 0.02197(12) 0.0145(2) Uani 1 1 d . . . . .
H1N H 0.296(2) 0.1771(8) -0.049(2) 0.032(5) Uiso 1 1 d . . . . .
N2 N 0.25844(13) 0.09220(5) 0.16818(12) 0.0138(2) Uani 1 1 d . . . . .
N3 N 0.41742(13) 0.14171(5) 0.38603(12) 0.0142(2) Uani 1 1 d . . . . .
N4 N 0.36458(14) 0.21350(5) 0.22942(13) 0.0157(2) Uani 1 1 d . . . . .
H4N H 0.342(2) 0.2479(9) 0.200(2) 0.033(5) Uiso 1 1 d . . . . .
C1 C 0.42775(15) 0.16889(6) 0.16118(14) 0.0128(2) Uani 1 1 d . . . . .
C2 C 0.20764(15) 0.11540(6) 0.03544(14) 0.0142(3) Uani 1 1 d . . . . .
C3 C 0.41609(15) 0.11455(6) 0.25514(14) 0.0124(2) Uani 1 1 d . . . . .
C4 C 0.36290(15) 0.19789(6) 0.36050(14) 0.0152(3) Uani 1 1 d . . . . .
C5 C 0.59228(15) 0.18233(6) 0.15871(14) 0.0144(3) Uani 1 1 d . . . . .
C6 C 0.64632(17) 0.15642(6) 0.05757(15) 0.0190(3) Uani 1 1 d . . . . .
H6A H 0.577322 0.132456 -0.014160 0.023 Uiso 1 1 calc R U . . .
C7 C 0.80102(18) 0.16543(7) 0.06093(18) 0.0253(3) Uani 1 1 d . . . . .
H7A H 0.837337 0.147369 -0.007899 0.030 Uiso 1 1 calc R U . . .
C8 C 0.90163(18) 0.20067(7) 0.16450(19) 0.0274(4) Uani 1 1 d . . . . .
H8A H 1.007146 0.206733 0.167109 0.033 Uiso 1 1 calc R U . . .
C9 C 0.84813(18) 0.22704(7) 0.26423(18) 0.0248(3) Uani 1 1 d . . . . .
H9A H 0.917015 0.251504 0.334741 0.030 Uiso 1 1 calc R U . . .
C10 C 0.69406(17) 0.21801(6) 0.26209(16) 0.0186(3) Uani 1 1 d . . . . .
H10A H 0.658382 0.236191 0.331160 0.022 Uiso 1 1 calc R U . . .
C11 C 0.54704(15) 0.07022(6) 0.27492(14) 0.0128(2) Uani 1 1 d . . . . .
C12 C 0.52568(16) 0.02301(6) 0.18426(15) 0.0162(3) Uani 1 1 d . . . . .
H12A H 0.425689 0.016730 0.112751 0.019 Uiso 1 1 calc R U . . .
C13 C 0.64921(17) -0.01514(6) 0.19720(16) 0.0201(3) Uani 1 1 d . . . . .
H13A H 0.632754 -0.047777 0.136016 0.024 Uiso 1 1 calc R U . . .
C14 C 0.79590(18) -0.00566(6) 0.29888(16) 0.0220(3) Uani 1 1 d . . . . .
H14A H 0.880543 -0.031607 0.307279 0.026 Uiso 1 1 calc R U . . .
C15 C 0.81931(17) 0.04171(7) 0.38852(16) 0.0218(3) Uani 1 1 d . . . . .
H15A H 0.920552 0.048462 0.457706 0.026 Uiso 1 1 calc R U . . .
C16 C 0.69546(16) 0.07947(6) 0.37785(15) 0.0167(3) Uani 1 1 d . . . . .
H16A H 0.711805 0.111586 0.440627 0.020 Uiso 1 1 calc R U . . .
C17 C 0.15499(16) 0.05694(6) 0.22174(15) 0.0185(3) Uani 1 1 d . . . . .
H17A H 0.046455 0.058407 0.151469 0.022 Uiso 1 1 calc R U . . .
H17B H 0.151694 0.074408 0.311420 0.022 Uiso 1 1 calc R U . . .
C18 C 0.20361(19) -0.00575(7) 0.2501(2) 0.0296(4) Uani 1 1 d . . . . .
H18A H 0.130648 -0.025615 0.288740 0.044 Uiso 1 1 calc R U . . .
H18B H 0.311261 -0.007891 0.319054 0.044 Uiso 1 1 calc R U . . .
H18C H 0.200413 -0.024339 0.160736 0.044 Uiso 1 1 calc R U . . .
C19 C 0.42014(17) 0.11097(6) 0.51597(14) 0.0178(3) Uani 1 1 d . . . . .
H19A H 0.439472 0.069373 0.505193 0.021 Uiso 1 1 calc R U . . .
H19B H 0.315282 0.114688 0.527349 0.021 Uiso 1 1 calc R U . . .
C20 C 0.54599(19) 0.13372(7) 0.64924(15) 0.0234(3) Uani 1 1 d . . . . .
H20A H 0.541028 0.112431 0.732667 0.035 Uiso 1 1 calc R U . . .
H20B H 0.527625 0.174914 0.660562 0.035 Uiso 1 1 calc R U . . .
H20C H 0.650609 0.128525 0.640580 0.035 Uiso 1 1 calc R U . . .
O1S O 0.20345(13) 0.32346(5) 0.20714(12) 0.0276(3) Uani 1 1 d . . . . .
O2S O -0.02993(12) 0.36532(5) 0.17732(12) 0.0240(2) Uani 1 1 d . . . . .
H2S H 0.017(3) 0.3729(10) 0.276(2) 0.054(7) Uiso 1 1 d . . . . .
C1S C 0.07136(19) 0.33655(6) 0.13419(16) 0.0228(3) Uani 1 1 d . . . . .
H1S H 0.037400 0.325079 0.036915 0.027 Uiso 1 1 calc R U . . .


_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 C2 1.2393(16) . ?
O2 C4 1.2268(16) . ?
N1 C2 1.3630(17) . ?
N1 C1 1.4489(17) . ?
N1 H1N 0.87(2) . ?
N2 C2 1.3553(17) . ?
N2 C17 1.4662(16) . ?
N2 C3 1.4810(16) . ?
N3 C4 1.3816(17) . ?
N3 C3 1.4439(16) . ?
N3 C19 1.4700(17) . ?
N4 C4 1.3599(17) . ?
N4 C1 1.4527(16) . ?
N4 H4N 0.85(2) . ?
C1 C5 1.5190(17) . ?
C1 C3 1.5916(18) . ?
C3 C11 1.5225(18) . ?
C5 C6 1.3933(19) . ?
C5 C10 1.393(2) . ?
C6 C7 1.3947(19) . ?
C6 H6A 0.9500 . ?
C7 C8 1.384(2) . ?
C7 H7A 0.9500 . ?
C8 C9 1.383(2) . ?
C8 H8A 0.9500 . ?
C9 C10 1.393(2) . ?
C9 H9A 0.9500 . ?
C10 H10A 0.9500 . ?
C11 C12 1.3885(19) . ?
C11 C16 1.3965(19) . ?
C12 C13 1.3893(19) . ?
C12 H12A 0.9500 . ?
C13 C14 1.381(2) . ?
C13 H13A 0.9500 . ?
C14 C15 1.384(2) . ?
C14 H14A 0.9500 . ?
C15 C16 1.3901(19) . ?
C15 H15A 0.9500 . ?
C16 H16A 0.9500 . ?
C17 C18 1.513(2) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 C20 1.517(2) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
O1S C1S 1.2019(19) . ?
O2S C1S 1.3117(18) . ?
O2S H2S 0.95(2) . ?
C1S H1S 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C1 110.41(11) . . ?
C2 N1 H1N 120.3(12) . . ?
C1 N1 H1N 120.3(12) . . ?
C2 N2 C17 121.99(11) . . ?
C2 N2 C3 111.84(10) . . ?
C17 N2 C3 125.45(11) . . ?
C4 N3 C3 110.42(10) . . ?
C4 N3 C19 121.09(11) . . ?
C3 N3 C19 125.27(11) . . ?
C4 N4 C1 113.19(11) . . ?
C4 N4 H4N 120.3(13) . . ?
C1 N4 H4N 126.0(13) . . ?
N1 C1 N4 112.94(11) . . ?
N1 C1 C5 112.35(10) . . ?
N4 C1 C5 113.50(11) . . ?
N1 C1 C3 101.60(10) . . ?
N4 C1 C3 99.89(10) . . ?
C5 C1 C3 115.42(10) . . ?
O1 C2 N2 124.64(12) . . ?
O1 C2 N1 126.07(12) . . ?
N2 C2 N1 109.28(11) . . ?
N3 C3 N2 113.21(10) . . ?
N3 C3 C11 113.98(11) . . ?
N2 C3 C11 112.63(11) . . ?
N3 C3 C1 101.85(10) . . ?
N2 C3 C1 99.90(10) . . ?
C11 C3 C1 113.97(10) . . ?
O2 C4 N4 127.00(13) . . ?
O2 C4 N3 125.06(12) . . ?
N4 C4 N3 107.94(11) . . ?
C6 C5 C10 119.16(12) . . ?
C6 C5 C1 120.20(12) . . ?
C10 C5 C1 120.55(12) . . ?
C5 C6 C7 120.46(14) . . ?
C5 C6 H6A 119.8 . . ?
C7 C6 H6A 119.8 . . ?
C8 C7 C6 120.00(14) . . ?
C8 C7 H7A 120.0 . . ?
C6 C7 H7A 120.0 . . ?
C9 C8 C7 119.82(14) . . ?
C9 C8 H8A 120.1 . . ?
C7 C8 H8A 120.1 . . ?
C8 C9 C10 120.53(15) . . ?
C8 C9 H9A 119.7 . . ?
C10 C9 H9A 119.7 . . ?
C5 C10 C9 120.03(14) . . ?
C5 C10 H10A 120.0 . . ?
C9 C10 H10A 120.0 . . ?
C12 C11 C16 119.05(12) . . ?
C12 C11 C3 120.99(12) . . ?
C16 C11 C3 119.74(12) . . ?
C11 C12 C13 120.59(13) . . ?
C11 C12 H12A 119.7 . . ?
C13 C12 H12A 119.7 . . ?
C14 C13 C12 120.09(13) . . ?
C14 C13 H13A 120.0 . . ?
C12 C13 H13A 120.0 . . ?
C13 C14 C15 119.85(13) . . ?
C13 C14 H14A 120.1 . . ?
C15 C14 H14A 120.1 . . ?
C14 C15 C16 120.35(13) . . ?
C14 C15 H15A 119.8 . . ?
C16 C15 H15A 119.8 . . ?
C15 C16 C11 120.05(13) . . ?
C15 C16 H16A 120.0 . . ?
C11 C16 H16A 120.0 . . ?
N2 C17 C18 114.98(12) . . ?
N2 C17 H17A 108.5 . . ?
C18 C17 H17A 108.5 . . ?
N2 C17 H17B 108.5 . . ?
C18 C17 H17B 108.5 . . ?
H17A C17 H17B 107.5 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N3 C19 C20 112.83(11) . . ?
N3 C19 H19A 109.0 . . ?
C20 C19 H19A 109.0 . . ?
N3 C19 H19B 109.0 . . ?
C20 C19 H19B 109.0 . . ?
H19A C19 H19B 107.8 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C1S O2S H2S 108.8(14) . . ?
O1S C1S O2S 125.62(14) . . ?
O1S C1S H1S 117.2 . . ?
O2S C1S H1S 117.2 . . ?

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
C2 N1 C1 N4 -79.95(14) . . . . ?
C2 N1 C1 C5 150.10(11) . . . . ?
C2 N1 C1 C3 26.16(13) . . . . ?
C4 N4 C1 N1 124.09(12) . . . . ?
C4 N4 C1 C5 -106.54(13) . . . . ?
C4 N4 C1 C3 16.90(14) . . . . ?
C17 N2 C2 O1 -10.3(2) . . . . ?
C3 N2 C2 O1 178.95(12) . . . . ?
C17 N2 C2 N1 171.11(11) . . . . ?
C3 N2 C2 N1 0.32(15) . . . . ?
C1 N1 C2 O1 163.44(13) . . . . ?
C1 N1 C2 N2 -17.96(15) . . . . ?
C4 N3 C3 N2 -81.58(13) . . . . ?
C19 N3 C3 N2 78.17(15) . . . . ?
C4 N3 C3 C11 147.96(11) . . . . ?
C19 N3 C3 C11 -52.29(16) . . . . ?
C4 N3 C3 C1 24.76(13) . . . . ?
C19 N3 C3 C1 -175.50(11) . . . . ?
C2 N2 C3 N3 122.58(12) . . . . ?
C17 N2 C3 N3 -47.82(17) . . . . ?
C2 N2 C3 C11 -106.29(12) . . . . ?
C17 N2 C3 C11 83.31(15) . . . . ?
C2 N2 C3 C1 15.02(13) . . . . ?
C17 N2 C3 C1 -155.38(12) . . . . ?
N1 C1 C3 N3 -139.92(10) . . . . ?
N4 C1 C3 N3 -23.83(12) . . . . ?
C5 C1 C3 N3 98.24(12) . . . . ?
N1 C1 C3 N2 -23.47(11) . . . . ?
N4 C1 C3 N2 92.62(10) . . . . ?
C5 C1 C3 N2 -145.30(11) . . . . ?
N1 C1 C3 C11 96.87(12) . . . . ?
N4 C1 C3 C11 -147.04(11) . . . . ?
C5 C1 C3 C11 -24.96(15) . . . . ?
C1 N4 C4 O2 177.40(13) . . . . ?
C1 N4 C4 N3 -2.56(15) . . . . ?
C3 N3 C4 O2 164.70(13) . . . . ?
C19 N3 C4 O2 4.0(2) . . . . ?
C3 N3 C4 N4 -15.33(15) . . . . ?
C19 N3 C4 N4 -176.06(11) . . . . ?
N1 C1 C5 C6 -27.47(17) . . . . ?
N4 C1 C5 C6 -157.14(12) . . . . ?
C3 C1 C5 C6 88.39(15) . . . . ?
N1 C1 C5 C10 156.18(12) . . . . ?
N4 C1 C5 C10 26.51(17) . . . . ?
C3 C1 C5 C10 -87.96(15) . . . . ?
C10 C5 C6 C7 0.9(2) . . . . ?
C1 C5 C6 C7 -175.52(13) . . . . ?
C5 C6 C7 C8 -0.5(2) . . . . ?
C6 C7 C8 C9 -0.2(2) . . . . ?
C7 C8 C9 C10 0.6(2) . . . . ?
C6 C5 C10 C9 -0.5(2) . . . . ?
C1 C5 C10 C9 175.86(13) . . . . ?
C8 C9 C10 C5 -0.2(2) . . . . ?
N3 C3 C11 C12 149.88(12) . . . . ?
N2 C3 C11 C12 19.14(17) . . . . ?
C1 C3 C11 C12 -93.77(14) . . . . ?
N3 C3 C11 C16 -35.57(16) . . . . ?
N2 C3 C11 C16 -166.32(11) . . . . ?
C1 C3 C11 C16 80.77(15) . . . . ?
C16 C11 C12 C13 1.1(2) . . . . ?
C3 C11 C12 C13 175.72(12) . . . . ?
C11 C12 C13 C14 -1.4(2) . . . . ?
C12 C13 C14 C15 0.4(2) . . . . ?
C13 C14 C15 C16 0.7(2) . . . . ?
C14 C15 C16 C11 -1.0(2) . . . . ?
C12 C11 C16 C15 0.0(2) . . . . ?
C3 C11 C16 C15 -174.63(12) . . . . ?
C2 N2 C17 C18 114.46(15) . . . . ?
C3 N2 C17 C18 -76.05(17) . . . . ?
C4 N3 C19 C20 -71.32(16) . . . . ?
C3 N3 C19 C20 130.94(13) . . . . ?

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
N4 H4N O1S 0.85(2) 2.16(2) 2.8979(16) 145.0(17) .
N1 H1N O2 0.87(2) 2.22(2) 2.8798(15) 132.4(16) 4_565
N1 H1N O1S 0.87(2) 2.290(19) 3.0029(16) 139.1(16) 4_565
N4 H4N O2 0.85(2) 2.561(19) 3.0626(15) 118.9(15) 4_565
O2S H2S O1 0.95(2) 1.64(2) 2.5814(15) 170(2) 4_566

_refine_diff_density_max         0.411
_refine_diff_density_min         -0.241
_refine_diff_density_rms         0.051



####################################################################### 
# 
# 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_1b
_database_code_depnum_ccdc_archive 'CCDC 2072845'
loop_
_audit_author_name
_audit_author_address
'Valentina Karnoukhova'
;A N Nesmeyanov Institute of Organoelement Compounds of Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2021-03-24 deposited with the CCDC.	2021-05-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H22 N4 O2'
_chemical_formula_sum            'C20 H22 N4 O2'
_chemical_formula_weight         350.41

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.3392(12)
_cell_length_b                   8.4864(8)
_cell_length_c                   34.065(3)
_cell_angle_alpha                90
_cell_angle_beta                 99.814(2)
_cell_angle_gamma                90
_cell_volume                     3515.0(6)
_cell_formula_units_Z            8
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    897
_cell_measurement_theta_min      3
_cell_measurement_theta_max      25

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.324
_exptl_crystal_F_000             1488
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.088
_shelx_estimated_absorpt_T_min   0.974
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6699
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX DUO diffractometer'
_diffrn_detector_type            'Bruker APEX II CCD area detector'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            45663
_diffrn_reflns_av_unetI/netI     0.0776
_diffrn_reflns_av_R_equivalents  0.0917
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -47
_diffrn_reflns_limit_l_max       47
_diffrn_reflns_theta_min         1.893
_diffrn_reflns_theta_max         29.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             10234
_reflns_number_gt                6428
_reflns_threshold_expression     I>2σ(I)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015b)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0491P)²+1.0473P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         10234
_refine_ls_number_parameters     489
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1030
_refine_ls_R_factor_gt           0.0586
_refine_ls_wR_factor_ref         0.1412
_refine_ls_wR_factor_gt          0.1199
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_restrained_S_all      1.009
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.38417(10) -0.16437(16) 0.19469(4) 0.0199(3) Uani 1 1 d . . . . .
O2 O 0.56067(11) 0.40100(15) 0.15873(4) 0.0236(3) Uani 1 1 d . . . . .
N1 N 0.44141(12) -0.02678(18) 0.14375(4) 0.0167(3) Uani 1 1 d . . . . .
H1N H 0.3771(18) -0.041(2) 0.1271(6) 0.024(6) Uiso 1 1 d . . . . .
N2 N 0.56708(12) -0.10628(17) 0.19438(4) 0.0158(3) Uani 1 1 d . . . . .
N3 N 0.62817(12) 0.16221(17) 0.18453(4) 0.0159(3) Uani 1 1 d . . . . .
N4 N 0.55257(13) 0.17421(18) 0.12062(5) 0.0182(3) Uani 1 1 d . . . . .
H4N H 0.503(2) 0.211(3) 0.1019(8) 0.051(8) Uiso 1 1 d . . . . .
C1 C 0.54474(14) 0.0099(2) 0.13038(5) 0.0154(3) Uani 1 1 d . . . . .
C2 C 0.45700(14) -0.1046(2) 0.17896(5) 0.0164(3) Uani 1 1 d . . . . .
C3 C 0.62694(14) -0.0033(2) 0.17149(5) 0.0150(3) Uani 1 1 d . . . . .
C4 C 0.57817(14) 0.2596(2) 0.15529(5) 0.0178(4) Uani 1 1 d . . . . .
C5 C 0.56223(14) -0.0989(2) 0.09657(5) 0.0166(4) Uani 1 1 d . . . . .
C6 C 0.54336(15) -0.2596(2) 0.09970(5) 0.0200(4) Uani 1 1 d . . . . .
H6A H 0.525768 -0.301149 0.123729 0.024 Uiso 1 1 calc R U . . .
C7 C 0.55003(15) -0.3595(2) 0.06803(6) 0.0228(4) Uani 1 1 d . . . . .
H7A H 0.538033 -0.469297 0.070589 0.027 Uiso 1 1 calc R U . . .
C8 C 0.57409(16) -0.2999(2) 0.03268(6) 0.0250(4) Uani 1 1 d . . . . .
H8A H 0.576739 -0.368182 0.010754 0.030 Uiso 1 1 calc R U . . .
C9 C 0.59424(17) -0.1408(3) 0.02945(6) 0.0266(4) Uani 1 1 d . . . . .
H9A H 0.611694 -0.099758 0.005346 0.032 Uiso 1 1 calc R U . . .
C10 C 0.58907(16) -0.0406(2) 0.06133(6) 0.0229(4) Uani 1 1 d . . . . .
H10A H 0.603982 0.068517 0.059020 0.027 Uiso 1 1 calc R U . . .
C11 C 0.74099(14) -0.0627(2) 0.16867(5) 0.0167(4) Uani 1 1 d . . . . .
C12 C 0.77090(15) -0.2200(2) 0.17494(6) 0.0209(4) Uani 1 1 d . . . . .
H12A H 0.718567 -0.294189 0.181060 0.025 Uiso 1 1 calc R U . . .
C13 C 0.87653(16) -0.2691(2) 0.17231(6) 0.0255(4) Uani 1 1 d . . . . .
H13A H 0.896655 -0.376321 0.177202 0.031 Uiso 1 1 calc R U . . .
C14 C 0.95293(16) -0.1628(3) 0.16260(6) 0.0268(4) Uani 1 1 d . . . . .
H14A H 1.025772 -0.196246 0.161405 0.032 Uiso 1 1 calc R U . . .
C15 C 0.92268(16) -0.0087(2) 0.15471(6) 0.0252(4) Uani 1 1 d . . . . .
H15A H 0.973970 0.063738 0.147068 0.030 Uiso 1 1 calc R U . . .
C16 C 0.81742(15) 0.0415(2) 0.15787(6) 0.0204(4) Uani 1 1 d . . . . .
H16A H 0.797495 0.148522 0.152563 0.025 Uiso 1 1 calc R U . . .
C17 C 0.60473(15) -0.1616(2) 0.23535(5) 0.0185(4) Uani 1 1 d . . . . .
H17A H 0.565116 -0.102939 0.253658 0.022 Uiso 1 1 calc R U . . .
H17B H 0.684164 -0.138602 0.243059 0.022 Uiso 1 1 calc R U . . .
C18 C 0.58601(16) -0.3372(2) 0.24002(6) 0.0239(4) Uani 1 1 d . . . . .
H18A H 0.603619 -0.365780 0.268262 0.036 Uiso 1 1 calc R U . . .
H18B H 0.633487 -0.396451 0.224995 0.036 Uiso 1 1 calc R U . . .
H18C H 0.508860 -0.362473 0.229817 0.036 Uiso 1 1 calc R U . . .
C19 C 0.67160(16) 0.2219(2) 0.22434(5) 0.0215(4) Uani 1 1 d . . . . .
H19A H 0.676763 0.133128 0.243428 0.026 Uiso 1 1 calc R U . . .
H19B H 0.618611 0.298903 0.231968 0.026 Uiso 1 1 calc R U . . .
C20 C 0.78305(17) 0.3000(3) 0.22837(7) 0.0341(5) Uani 1 1 d . . . . .
H20A H 0.802037 0.347097 0.254910 0.051 Uiso 1 1 calc R U . . .
H20B H 0.780870 0.382282 0.208072 0.051 Uiso 1 1 calc R U . . .
H20C H 0.838506 0.221098 0.224723 0.051 Uiso 1 1 calc R U . . .
O1A O 0.38459(10) 0.31022(16) 0.06359(4) 0.0216(3) Uani 1 1 d . . . . .
O2A O 0.23038(11) 0.91266(15) 0.09973(4) 0.0233(3) Uani 1 1 d . . . . .
N1A N 0.33270(13) 0.45909(19) 0.11423(5) 0.0183(3) Uani 1 1 d . . . . .
H1NA H 0.394(2) 0.445(3) 0.1305(7) 0.034(6) Uiso 1 1 d . . . . .
N2A N 0.20722(12) 0.39772(18) 0.06173(4) 0.0177(3) Uani 1 1 d . . . . .
N3A N 0.17279(12) 0.67734(18) 0.07036(4) 0.0185(3) Uani 1 1 d . . . . .
N4A N 0.23247(13) 0.68061(18) 0.13575(5) 0.0193(3) Uani 1 1 d . . . . .
H4NA H 0.283(2) 0.723(3) 0.1583(8) 0.048(7) Uiso 1 1 d . . . . .
C1A C 0.23052(14) 0.5151(2) 0.12555(5) 0.0163(4) Uani 1 1 d . . . . .
C2A C 0.31576(15) 0.3825(2) 0.07882(5) 0.0179(4) Uani 1 1 d . . . . .
C3A C 0.15429(14) 0.5149(2) 0.08265(5) 0.0166(4) Uani 1 1 d . . . . .
C4A C 0.21434(14) 0.7703(2) 0.10169(5) 0.0182(4) Uani 1 1 d . . . . .
C5A C 0.19364(14) 0.4118(2) 0.15715(5) 0.0174(4) Uani 1 1 d . . . . .
C6A C 0.21647(15) 0.2516(2) 0.15819(6) 0.0212(4) Uani 1 1 d . . . . .
H6AA H 0.256522 0.207588 0.139365 0.025 Uiso 1 1 calc R U . . .
C7A C 0.18155(16) 0.1551(2) 0.18633(6) 0.0254(4) Uani 1 1 d . . . . .
H7AA H 0.197233 0.045421 0.186652 0.030 Uiso 1 1 calc R U . . .
C8A C 0.12397(17) 0.2183(3) 0.21390(6) 0.0275(4) Uani 1 1 d . . . . .
H8AA H 0.100099 0.152161 0.233262 0.033 Uiso 1 1 calc R U . . .
C9A C 0.10103(16) 0.3774(3) 0.21339(6) 0.0270(4) Uani 1 1 d . . . . .
H9AA H 0.061331 0.420686 0.232395 0.032 Uiso 1 1 calc R U . . .
C10A C 0.13582(15) 0.4745(2) 0.18514(6) 0.0229(4) Uani 1 1 d . . . . .
H10B H 0.120042 0.584048 0.184954 0.027 Uiso 1 1 calc R U . . .
C11A C 0.03347(14) 0.4818(2) 0.08206(5) 0.0182(4) Uani 1 1 d . . . . .
C12A C -0.00354(15) 0.3275(2) 0.08422(5) 0.0218(4) Uani 1 1 d . . . . .
H12B H 0.046800 0.242318 0.085251 0.026 Uiso 1 1 calc R U . . .
C13A C -0.11360(17) 0.2982(3) 0.08486(6) 0.0273(5) Uani 1 1 d . . . . .
H13B H -0.138601 0.192612 0.085875 0.033 Uiso 1 1 calc R U . . .
C14A C -0.18736(17) 0.4211(3) 0.08403(6) 0.0302(5) Uani 1 1 d . . . . .
H14B H -0.262691 0.400248 0.084660 0.036 Uiso 1 1 calc R U . . .
C15A C -0.15117(16) 0.5736(3) 0.08230(6) 0.0287(5) Uani 1 1 d . . . . .
H15B H -0.201460 0.658649 0.081880 0.034 Uiso 1 1 calc R U . . .
C16A C -0.04136(15) 0.6035(2) 0.08118(6) 0.0220(4) Uani 1 1 d . . . . .
H16B H -0.017115 0.709311 0.079772 0.026 Uiso 1 1 calc R U . . .
C17A C 0.16926(16) 0.3485(2) 0.02044(5) 0.0210(4) Uani 1 1 d . . . . .
H17C H 0.222890 0.384468 0.003811 0.025 Uiso 1 1 calc R U . . .
H17D H 0.098024 0.400204 0.010376 0.025 Uiso 1 1 calc R U . . .
C18A C 0.15525(18) 0.1713(2) 0.01609(6) 0.0279(4) Uani 1 1 d . . . . .
H18D H 0.143883 0.143021 -0.012210 0.042 Uiso 1 1 calc R U . . .
H18E H 0.091410 0.137871 0.027615 0.042 Uiso 1 1 calc R U . . .
H18F H 0.221398 0.118548 0.030050 0.042 Uiso 1 1 calc R U . . .
C19A C 0.15524(16) 0.7389(2) 0.02989(5) 0.0214(4) Uani 1 1 d . . . . .
H19C H 0.118443 0.842739 0.029361 0.026 Uiso 1 1 calc R U . . .
H19D H 0.106125 0.666748 0.012223 0.026 Uiso 1 1 calc R U . . .
C20A C 0.26269(18) 0.7568(3) 0.01432(6) 0.0305(5) Uani 1 1 d . . . . .
H20D H 0.248500 0.805832 -0.012096 0.046 Uiso 1 1 calc R U . . .
H20E H 0.295895 0.652734 0.012420 0.046 Uiso 1 1 calc R U . . .
H20F H 0.313092 0.823228 0.032594 0.046 Uiso 1 1 calc R U . . .


_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 C2 1.231(2) . ?
O2 C4 1.228(2) . ?
N1 C2 1.354(2) . ?
N1 C1 1.459(2) . ?
N1 H1N 0.90(2) . ?
N2 C2 1.370(2) . ?
N2 C3 1.454(2) . ?
N2 C17 1.471(2) . ?
N3 C4 1.359(2) . ?
N3 C19 1.461(2) . ?
N3 C3 1.473(2) . ?
N4 C4 1.376(2) . ?
N4 C1 1.441(2) . ?
N4 H4N 0.87(3) . ?
C1 C5 1.520(2) . ?
C1 C3 1.587(2) . ?
C3 C11 1.513(2) . ?
C5 C10 1.389(3) . ?
C5 C6 1.390(3) . ?
C6 C7 1.386(3) . ?
C6 H6A 0.9500 . ?
C7 C8 1.384(3) . ?
C7 H7A 0.9500 . ?
C8 C9 1.381(3) . ?
C8 H8A 0.9500 . ?
C9 C10 1.390(3) . ?
C9 H9A 0.9500 . ?
C10 H10A 0.9500 . ?
C11 C16 1.387(3) . ?
C11 C12 1.392(3) . ?
C12 C13 1.386(3) . ?
C12 H12A 0.9500 . ?
C13 C14 1.385(3) . ?
C13 H13A 0.9500 . ?
C14 C15 1.374(3) . ?
C14 H14A 0.9500 . ?
C15 C16 1.388(3) . ?
C15 H15A 0.9500 . ?
C16 H16A 0.9500 . ?
C17 C18 1.520(3) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 C20 1.511(3) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
O1A C2A 1.232(2) . ?
O2A C4A 1.228(2) . ?
N1A C2A 1.355(2) . ?
N1A C1A 1.460(2) . ?
N1A H1NA 0.87(2) . ?
N2A C2A 1.372(2) . ?
N2A C3A 1.443(2) . ?
N2A C17A 1.465(2) . ?
N3A C4A 1.356(2) . ?
N3A C19A 1.456(2) . ?
N3A C3A 1.470(2) . ?
N4A C4A 1.373(2) . ?
N4A C1A 1.446(2) . ?
N4A H4NA 0.97(3) . ?
C1A C5A 1.517(3) . ?
C1A C3A 1.597(2) . ?
C3A C11A 1.514(2) . ?
C5A C6A 1.388(3) . ?
C5A C10A 1.390(3) . ?
C6A C7A 1.384(3) . ?
C6A H6AA 0.9500 . ?
C7A C8A 1.379(3) . ?
C7A H7AA 0.9500 . ?
C8A C9A 1.379(3) . ?
C8A H8AA 0.9500 . ?
C9A C10A 1.389(3) . ?
C9A H9AA 0.9500 . ?
C10A H10B 0.9500 . ?
C11A C16A 1.383(3) . ?
C11A C12A 1.393(3) . ?
C12A C13A 1.385(3) . ?
C12A H12B 0.9500 . ?
C13A C14A 1.382(3) . ?
C13A H13B 0.9500 . ?
C14A C15A 1.374(3) . ?
C14A H14B 0.9500 . ?
C15A C16A 1.385(3) . ?
C15A H15B 0.9500 . ?
C16A H16B 0.9500 . ?
C17A C18A 1.518(3) . ?
C17A H17C 0.9900 . ?
C17A H17D 0.9900 . ?
C18A H18D 0.9800 . ?
C18A H18E 0.9800 . ?
C18A H18F 0.9800 . ?
C19A C20A 1.517(3) . ?
C19A H19C 0.9900 . ?
C19A H19D 0.9900 . ?
C20A H20D 0.9800 . ?
C20A H20E 0.9800 . ?
C20A H20F 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
C2 N1 C1 112.39(14) . . ?
C2 N1 H1N 117.8(13) . . ?
C1 N1 H1N 123.8(13) . . ?
C2 N2 C3 110.43(14) . . ?
C2 N2 C17 119.95(14) . . ?
C3 N2 C17 126.42(14) . . ?
C4 N3 C19 121.22(15) . . ?
C4 N3 C3 112.28(14) . . ?
C19 N3 C3 126.43(14) . . ?
C4 N4 C1 109.04(15) . . ?
C4 N4 H4N 118.1(18) . . ?
C1 N4 H4N 117.0(18) . . ?
N4 C1 N1 112.03(14) . . ?
N4 C1 C5 112.90(15) . . ?
N1 C1 C5 110.58(14) . . ?
N4 C1 C3 102.37(13) . . ?
N1 C1 C3 99.83(13) . . ?
C5 C1 C3 118.29(14) . . ?
O1 C2 N1 125.62(16) . . ?
O1 C2 N2 125.32(17) . . ?
N1 C2 N2 109.06(15) . . ?
N2 C3 N3 113.05(14) . . ?
N2 C3 C11 113.40(14) . . ?
N3 C3 C11 112.00(14) . . ?
N2 C3 C1 102.07(13) . . ?
N3 C3 C1 99.84(13) . . ?
C11 C3 C1 115.41(14) . . ?
O2 C4 N3 126.13(17) . . ?
O2 C4 N4 125.30(17) . . ?
N3 C4 N4 108.55(16) . . ?
C10 C5 C6 118.88(17) . . ?
C10 C5 C1 121.60(16) . . ?
C6 C5 C1 119.36(16) . . ?
C7 C6 C5 120.50(18) . . ?
C7 C6 H6A 119.8 . . ?
C5 C6 H6A 119.8 . . ?
C8 C7 C6 120.27(19) . . ?
C8 C7 H7A 119.9 . . ?
C6 C7 H7A 119.9 . . ?
C9 C8 C7 119.64(18) . . ?
C9 C8 H8A 120.2 . . ?
C7 C8 H8A 120.2 . . ?
C8 C9 C10 120.24(18) . . ?
C8 C9 H9A 119.9 . . ?
C10 C9 H9A 119.9 . . ?
C5 C10 C9 120.44(18) . . ?
C5 C10 H10A 119.8 . . ?
C9 C10 H10A 119.8 . . ?
C16 C11 C12 118.52(17) . . ?
C16 C11 C3 119.11(16) . . ?
C12 C11 C3 122.32(16) . . ?
C13 C12 C11 120.42(18) . . ?
C13 C12 H12A 119.8 . . ?
C11 C12 H12A 119.8 . . ?
C14 C13 C12 120.35(19) . . ?
C14 C13 H13A 119.8 . . ?
C12 C13 H13A 119.8 . . ?
C15 C14 C13 119.57(18) . . ?
C15 C14 H14A 120.2 . . ?
C13 C14 H14A 120.2 . . ?
C14 C15 C16 120.24(19) . . ?
C14 C15 H15A 119.9 . . ?
C16 C15 H15A 119.9 . . ?
C11 C16 C15 120.80(18) . . ?
C11 C16 H16A 119.6 . . ?
C15 C16 H16A 119.6 . . ?
N2 C17 C18 112.54(15) . . ?
N2 C17 H17A 109.1 . . ?
C18 C17 H17A 109.1 . . ?
N2 C17 H17B 109.1 . . ?
C18 C17 H17B 109.1 . . ?
H17A C17 H17B 107.8 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N3 C19 C20 114.84(16) . . ?
N3 C19 H19A 108.6 . . ?
C20 C19 H19A 108.6 . . ?
N3 C19 H19B 108.6 . . ?
C20 C19 H19B 108.6 . . ?
H19A C19 H19B 107.5 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C2A N1A C1A 112.50(15) . . ?
C2A N1A H1NA 119.2(15) . . ?
C1A N1A H1NA 125.3(15) . . ?
C2A N2A C3A 110.28(14) . . ?
C2A N2A C17A 120.62(15) . . ?
C3A N2A C17A 124.96(14) . . ?
C4A N3A C19A 120.81(15) . . ?
C4A N3A C3A 112.17(14) . . ?
C19A N3A C3A 126.97(15) . . ?
C4A N4A C1A 109.97(15) . . ?
C4A N4A H4NA 117.1(15) . . ?
C1A N4A H4NA 122.1(15) . . ?
N4A C1A N1A 113.59(15) . . ?
N4A C1A C5A 112.69(15) . . ?
N1A C1A C5A 112.11(14) . . ?
N4A C1A C3A 101.76(13) . . ?
N1A C1A C3A 99.11(14) . . ?
C5A C1A C3A 116.58(14) . . ?
O1A C2A N1A 126.96(17) . . ?
O1A C2A N2A 124.16(17) . . ?
N1A C2A N2A 108.88(16) . . ?
N2A C3A N3A 113.59(15) . . ?
N2A C3A C11A 113.13(15) . . ?
N3A C3A C11A 111.78(14) . . ?
N2A C3A C1A 101.95(13) . . ?
N3A C3A C1A 99.44(13) . . ?
C11A C3A C1A 115.94(14) . . ?
O2A C4A N3A 124.92(17) . . ?
O2A C4A N4A 125.90(17) . . ?
N3A C4A N4A 109.16(16) . . ?
C6A C5A C10A 118.86(17) . . ?
C6A C5A C1A 120.01(16) . . ?
C10A C5A C1A 121.12(17) . . ?
C7A C6A C5A 120.76(18) . . ?
C7A C6A H6AA 119.6 . . ?
C5A C6A H6AA 119.6 . . ?
C8A C7A C6A 119.93(19) . . ?
C8A C7A H7AA 120.0 . . ?
C6A C7A H7AA 120.0 . . ?
C7A C8A C9A 120.03(19) . . ?
C7A C8A H8AA 120.0 . . ?
C9A C8A H8AA 120.0 . . ?
C8A C9A C10A 120.17(19) . . ?
C8A C9A H9AA 119.9 . . ?
C10A C9A H9AA 119.9 . . ?
C9A C10A C5A 120.24(19) . . ?
C9A C10A H10B 119.9 . . ?
C5A C10A H10B 119.9 . . ?
C16A C11A C12A 118.67(17) . . ?
C16A C11A C3A 120.93(17) . . ?
C12A C11A C3A 120.33(16) . . ?
C13A C12A C11A 120.09(19) . . ?
C13A C12A H12B 120.0 . . ?
C11A C12A H12B 120.0 . . ?
C14A C13A C12A 120.6(2) . . ?
C14A C13A H13B 119.7 . . ?
C12A C13A H13B 119.7 . . ?
C15A C14A C13A 119.64(19) . . ?
C15A C14A H14B 120.2 . . ?
C13A C14A H14B 120.2 . . ?
C14A C15A C16A 120.01(19) . . ?
C14A C15A H15B 120.0 . . ?
C16A C15A H15B 120.0 . . ?
C11A C16A C15A 121.02(19) . . ?
C11A C16A H16B 119.5 . . ?
C15A C16A H16B 119.5 . . ?
N2A C17A C18A 112.88(15) . . ?
N2A C17A H17C 109.0 . . ?
C18A C17A H17C 109.0 . . ?
N2A C17A H17D 109.0 . . ?
C18A C17A H17D 109.0 . . ?
H17C C17A H17D 107.8 . . ?
C17A C18A H18D 109.5 . . ?
C17A C18A H18E 109.5 . . ?
H18D C18A H18E 109.5 . . ?
C17A C18A H18F 109.5 . . ?
H18D C18A H18F 109.5 . . ?
H18E C18A H18F 109.5 . . ?
N3A C19A C20A 111.65(16) . . ?
N3A C19A H19C 109.3 . . ?
C20A C19A H19C 109.3 . . ?
N3A C19A H19D 109.3 . . ?
C20A C19A H19D 109.3 . . ?
H19C C19A H19D 108.0 . . ?
C19A C20A H20D 109.5 . . ?
C19A C20A H20E 109.5 . . ?
H20D C20A H20E 109.5 . . ?
C19A C20A H20F 109.5 . . ?
H20D C20A H20F 109.5 . . ?
H20E C20A H20F 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
C4 N4 C1 N1 77.28(18) . . . . ?
C4 N4 C1 C5 -157.09(14) . . . . ?
C4 N4 C1 C3 -28.82(18) . . . . ?
C2 N1 C1 N4 -128.07(16) . . . . ?
C2 N1 C1 C5 105.03(17) . . . . ?
C2 N1 C1 C3 -20.34(18) . . . . ?
C1 N1 C2 O1 -171.55(17) . . . . ?
C1 N1 C2 N2 8.4(2) . . . . ?
C3 N2 C2 O1 -170.66(17) . . . . ?
C17 N2 C2 O1 -9.6(3) . . . . ?
C3 N2 C2 N1 9.4(2) . . . . ?
C17 N2 C2 N1 170.45(15) . . . . ?
C2 N2 C3 N3 85.17(17) . . . . ?
C17 N2 C3 N3 -74.4(2) . . . . ?
C2 N2 C3 C11 -145.95(15) . . . . ?
C17 N2 C3 C11 54.5(2) . . . . ?
C2 N2 C3 C1 -21.15(18) . . . . ?
C17 N2 C3 C1 179.30(15) . . . . ?
C4 N3 C3 N2 -118.14(16) . . . . ?
C19 N3 C3 N2 58.9(2) . . . . ?
C4 N3 C3 C11 112.26(16) . . . . ?
C19 N3 C3 C11 -70.7(2) . . . . ?
C4 N3 C3 C1 -10.41(17) . . . . ?
C19 N3 C3 C1 166.61(15) . . . . ?
N4 C1 C3 N2 139.00(14) . . . . ?
N1 C1 C3 N2 23.68(16) . . . . ?
C5 C1 C3 N2 -96.21(17) . . . . ?
N4 C1 C3 N3 22.68(16) . . . . ?
N1 C1 C3 N3 -92.64(14) . . . . ?
C5 C1 C3 N3 147.46(15) . . . . ?
N4 C1 C3 C11 -97.55(17) . . . . ?
N1 C1 C3 C11 147.13(15) . . . . ?
C5 C1 C3 C11 27.2(2) . . . . ?
C19 N3 C4 O2 -2.5(3) . . . . ?
C3 N3 C4 O2 174.67(17) . . . . ?
C19 N3 C4 N4 175.93(15) . . . . ?
C3 N3 C4 N4 -6.9(2) . . . . ?
C1 N4 C4 O2 -158.01(17) . . . . ?
C1 N4 C4 N3 23.51(19) . . . . ?
N4 C1 C5 C10 3.5(2) . . . . ?
N1 C1 C5 C10 129.86(17) . . . . ?
C3 C1 C5 C10 -115.98(19) . . . . ?
N4 C1 C5 C6 -171.89(16) . . . . ?
N1 C1 C5 C6 -45.5(2) . . . . ?
C3 C1 C5 C6 68.7(2) . . . . ?
C10 C5 C6 C7 -0.7(3) . . . . ?
C1 C5 C6 C7 174.75(16) . . . . ?
C5 C6 C7 C8 -0.9(3) . . . . ?
C6 C7 C8 C9 1.7(3) . . . . ?
C7 C8 C9 C10 -0.8(3) . . . . ?
C6 C5 C10 C9 1.6(3) . . . . ?
C1 C5 C10 C9 -173.79(17) . . . . ?
C8 C9 C10 C5 -0.8(3) . . . . ?
N2 C3 C11 C16 -162.00(16) . . . . ?
N3 C3 C11 C16 -32.6(2) . . . . ?
C1 C3 C11 C16 80.8(2) . . . . ?
N2 C3 C11 C12 20.7(2) . . . . ?
N3 C3 C11 C12 150.15(16) . . . . ?
C1 C3 C11 C12 -96.5(2) . . . . ?
C16 C11 C12 C13 3.1(3) . . . . ?
C3 C11 C12 C13 -179.59(17) . . . . ?
C11 C12 C13 C14 -1.3(3) . . . . ?
C12 C13 C14 C15 -1.4(3) . . . . ?
C13 C14 C15 C16 2.3(3) . . . . ?
C12 C11 C16 C15 -2.2(3) . . . . ?
C3 C11 C16 C15 -179.58(16) . . . . ?
C14 C15 C16 C11 -0.5(3) . . . . ?
C2 N2 C17 C18 68.0(2) . . . . ?
C3 N2 C17 C18 -134.16(17) . . . . ?
C4 N3 C19 C20 -80.7(2) . . . . ?
C3 N3 C19 C20 102.5(2) . . . . ?
C4A N4A C1A N1A 79.58(18) . . . . ?
C4A N4A C1A C5A -151.54(15) . . . . ?
C4A N4A C1A C3A -25.93(18) . . . . ?
C2A N1A C1A N4A -127.94(16) . . . . ?
C2A N1A C1A C5A 102.89(17) . . . . ?
C2A N1A C1A C3A -20.77(18) . . . . ?
C1A N1A C2A O1A -172.73(17) . . . . ?
C1A N1A C2A N2A 7.4(2) . . . . ?
C3A N2A C2A O1A -168.01(17) . . . . ?
C17A N2A C2A O1A -9.8(3) . . . . ?
C3A N2A C2A N1A 11.9(2) . . . . ?
C17A N2A C2A N1A 170.08(15) . . . . ?
C2A N2A C3A N3A 82.17(18) . . . . ?
C17A N2A C3A N3A -74.9(2) . . . . ?
C2A N2A C3A C11A -149.02(15) . . . . ?
C17A N2A C3A C11A 53.9(2) . . . . ?
C2A N2A C3A C1A -23.81(18) . . . . ?
C17A N2A C3A C1A 179.12(15) . . . . ?
C4A N3A C3A N2A -125.82(16) . . . . ?
C19A N3A C3A N2A 51.7(2) . . . . ?
C4A N3A C3A C11A 104.69(17) . . . . ?
C19A N3A C3A C11A -77.8(2) . . . . ?
C4A N3A C3A C1A -18.26(18) . . . . ?
C19A N3A C3A C1A 159.21(16) . . . . ?
N4A C1A C3A N2A 142.07(14) . . . . ?
N1A C1A C3A N2A 25.49(16) . . . . ?
C5A C1A C3A N2A -94.93(17) . . . . ?
N4A C1A C3A N3A 25.34(16) . . . . ?
N1A C1A C3A N3A -91.24(14) . . . . ?
C5A C1A C3A N3A 148.34(15) . . . . ?
N4A C1A C3A C11A -94.60(17) . . . . ?
N1A C1A C3A C11A 148.82(15) . . . . ?
C5A C1A C3A C11A 28.4(2) . . . . ?
C19A N3A C4A O2A 7.3(3) . . . . ?
C3A N3A C4A O2A -175.05(17) . . . . ?
C19A N3A C4A N4A -174.32(15) . . . . ?
C3A N3A C4A N4A 3.3(2) . . . . ?
C1A N4A C4A O2A -165.97(17) . . . . ?
C1A N4A C4A N3A 15.7(2) . . . . ?
N4A C1A C5A C6A -161.49(16) . . . . ?
N1A C1A C5A C6A -31.8(2) . . . . ?
C3A C1A C5A C6A 81.4(2) . . . . ?
N4A C1A C5A C10A 19.2(2) . . . . ?
N1A C1A C5A C10A 148.85(17) . . . . ?
C3A C1A C5A C10A -97.9(2) . . . . ?
C10A C5A C6A C7A 0.6(3) . . . . ?
C1A C5A C6A C7A -178.73(17) . . . . ?
C5A C6A C7A C8A -0.4(3) . . . . ?
C6A C7A C8A C9A 0.1(3) . . . . ?
C7A C8A C9A C10A 0.0(3) . . . . ?
C8A C9A C10A C5A 0.2(3) . . . . ?
C6A C5A C10A C9A -0.5(3) . . . . ?
C1A C5A C10A C9A 178.83(17) . . . . ?
N2A C3A C11A C16A -146.68(17) . . . . ?
N3A C3A C11A C16A -16.9(2) . . . . ?
C1A C3A C11A C16A 96.1(2) . . . . ?
N2A C3A C11A C12A 36.2(2) . . . . ?
N3A C3A C11A C12A 165.97(16) . . . . ?
C1A C3A C11A C12A -81.0(2) . . . . ?
C16A C11A C12A C13A 0.9(3) . . . . ?
C3A C11A C12A C13A 178.08(17) . . . . ?
C11A C12A C13A C14A -1.1(3) . . . . ?
C12A C13A C14A C15A 0.4(3) . . . . ?
C13A C14A C15A C16A 0.4(3) . . . . ?
C12A C11A C16A C15A -0.2(3) . . . . ?
C3A C11A C16A C15A -177.29(17) . . . . ?
C14A C15A C16A C11A -0.5(3) . . . . ?
C2A N2A C17A C18A 78.1(2) . . . . ?
C3A N2A C17A C18A -127.03(18) . . . . ?
C4A N3A C19A C20A 74.9(2) . . . . ?
C3A N3A C19A C20A -102.4(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
N1A H1NA O2 0.87(2) 2.15(2) 3.000(2) 167(2) .
N4 H4N O1A 0.87(3) 1.97(3) 2.834(2) 174(3) .
N1 H1N O2A 0.90(2) 1.93(2) 2.822(2) 169.8(19) 1_545
N4A H4NA O1 0.97(3) 1.87(3) 2.826(2) 169(2) 1_565

_refine_diff_density_max         0.344
_refine_diff_density_min         -0.270
_refine_diff_density_rms         0.058



####################################################################### 
# 
# 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_1b-dioxane
_database_code_depnum_ccdc_archive 'CCDC 2072853'
loop_
_audit_author_name
_audit_author_address
'Valentina Karnoukhova'
;A N Nesmeyanov Institute of Organoelement Compounds of Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2021-03-24 deposited with the CCDC.	2021-05-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H22 N4 O2, C4 H8 O2'
_chemical_formula_sum            'C24 H30 N4 O4'
_chemical_formula_weight         438.52

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.2337(9)
_cell_length_b                   10.7773(12)
_cell_length_c                   12.9970(14)
_cell_angle_alpha                98.025(3)
_cell_angle_beta                 97.959(3)
_cell_angle_gamma                91.457(3)
_cell_volume                     1129.8(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    226
_cell_measurement_theta_min      3
_cell_measurement_theta_max      25

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_F_000             468
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.290
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.210
_exptl_absorpt_coefficient_mu    0.089
_shelx_estimated_absorpt_T_min   0.975
_shelx_estimated_absorpt_T_max   0.982
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6763
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX DUO diffractometer'
_diffrn_detector_type            'Bruker APEX II CCD area detector'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15161
_diffrn_reflns_av_unetI/netI     0.0649
_diffrn_reflns_av_R_equivalents  0.0452
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.910
_diffrn_reflns_theta_max         29.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             6587
_reflns_number_gt                4495
_reflns_threshold_expression     I>2σ(I)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015b)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0520P)²+0.1164P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6587
_refine_ls_number_parameters     299
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0839
_refine_ls_R_factor_gt           0.0532
_refine_ls_wR_factor_ref         0.1283
_refine_ls_wR_factor_gt          0.1141
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_restrained_S_all      1.030
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.28272(13) 0.99041(10) 1.00580(8) 0.0218(2) Uani 1 1 d . . . . .
O2 O 0.28484(13) 0.46101(10) 0.96327(8) 0.0216(2) Uani 1 1 d . . . . .
N1 N 0.43585(15) 0.85247(11) 0.91147(10) 0.0171(3) Uani 1 1 d . . . . .
H1N H 0.530(2) 0.8911(18) 0.9370(15) 0.038(6) Uiso 1 1 d . . . . .
N2 N 0.17017(14) 0.81078(11) 0.90176(9) 0.0157(2) Uani 1 1 d . . . . .
N3 N 0.18241(14) 0.58744(11) 0.84305(9) 0.0156(2) Uani 1 1 d . . . . .
N4 N 0.43157(15) 0.63328(11) 0.93129(10) 0.0161(2) Uani 1 1 d . . . . .
H4N H 0.530(2) 0.6112(17) 0.9609(14) 0.030(5) Uiso 1 1 d . . . . .
C1 C 0.41393(17) 0.72540(13) 0.85915(11) 0.0147(3) Uani 1 1 d . . . . .
C2 C 0.29544(17) 0.89371(13) 0.94570(11) 0.0166(3) Uani 1 1 d . . . . .
C3 C 0.22060(16) 0.71326(12) 0.82430(11) 0.0144(3) Uani 1 1 d . . . . .
C4 C 0.29925(17) 0.55203(13) 0.91748(11) 0.0163(3) Uani 1 1 d . . . . .
C5 C 0.51584(16) 0.69883(13) 0.77107(11) 0.0164(3) Uani 1 1 d . . . . .
C6 C 0.57184(19) 0.79593(15) 0.72337(12) 0.0230(3) Uani 1 1 d . . . . .
H6A H 0.549998 0.880222 0.747886 0.028 Uiso 1 1 calc R U . . .
C7 C 0.6597(2) 0.76966(17) 0.63984(13) 0.0290(4) Uani 1 1 d . . . . .
H7A H 0.700942 0.836402 0.608746 0.035 Uiso 1 1 calc R U . . .
C8 C 0.6877(2) 0.64759(17) 0.60172(13) 0.0299(4) Uani 1 1 d . . . . .
H8A H 0.745855 0.630091 0.543508 0.036 Uiso 1 1 calc R U . . .
C9 C 0.6311(2) 0.55086(16) 0.64814(13) 0.0274(4) Uani 1 1 d . . . . .
H9A H 0.649238 0.466468 0.621550 0.033 Uiso 1 1 calc R U . . .
C10 C 0.54793(19) 0.57667(15) 0.73337(12) 0.0223(3) Uani 1 1 d . . . . .
H10A H 0.512304 0.509784 0.766530 0.027 Uiso 1 1 calc R U . . .
C11 C 0.16360(17) 0.73591(13) 0.71309(11) 0.0161(3) Uani 1 1 d . . . . .
C12 C 0.12256(18) 0.85519(14) 0.69320(12) 0.0201(3) Uani 1 1 d . . . . .
H12A H 0.124933 0.921562 0.749857 0.024 Uiso 1 1 calc R U . . .
C13 C 0.0781(2) 0.87780(15) 0.59097(12) 0.0253(3) Uani 1 1 d . . . . .
H13A H 0.050033 0.959765 0.578115 0.030 Uiso 1 1 calc R U . . .
C14 C 0.0741(2) 0.78291(16) 0.50776(12) 0.0254(3) Uani 1 1 d . . . . .
H14A H 0.042848 0.798896 0.437864 0.030 Uiso 1 1 calc R U . . .
C15 C 0.11629(18) 0.66377(15) 0.52719(12) 0.0216(3) Uani 1 1 d . . . . .
H15A H 0.114442 0.597768 0.470295 0.026 Uiso 1 1 calc R U . . .
C16 C 0.16097(17) 0.64064(14) 0.62893(11) 0.0183(3) Uani 1 1 d . . . . .
H16A H 0.190187 0.558795 0.641468 0.022 Uiso 1 1 calc R U . . .
C17 C 0.00054(17) 0.83124(14) 0.91789(12) 0.0179(3) Uani 1 1 d . . . . .
H17A H -0.074111 0.786215 0.857142 0.021 Uiso 1 1 calc R U . . .
H17B H -0.019465 0.921850 0.921743 0.021 Uiso 1 1 calc R U . . .
C18 C -0.0377(2) 0.78613(15) 1.01739(13) 0.0253(3) Uani 1 1 d . . . . .
H18A H -0.153049 0.799569 1.024634 0.038 Uiso 1 1 calc R U . . .
H18B H 0.032796 0.833079 1.078003 0.038 Uiso 1 1 calc R U . . .
H18C H -0.017488 0.696528 1.013993 0.038 Uiso 1 1 calc R U . . .
C19 C 0.01798(17) 0.52617(14) 0.82145(12) 0.0195(3) Uani 1 1 d . . . . .
H19A H -0.056043 0.575996 0.778316 0.023 Uiso 1 1 calc R U . . .
H19B H -0.025384 0.523908 0.888535 0.023 Uiso 1 1 calc R U . . .
C20 C 0.0184(2) 0.39361(14) 0.76425(12) 0.0238(3) Uani 1 1 d . . . . .
H20A H -0.094188 0.357460 0.748461 0.036 Uiso 1 1 calc R U . . .
H20B H 0.085801 0.342469 0.808671 0.036 Uiso 1 1 calc R U . . .
H20C H 0.063997 0.395193 0.698643 0.036 Uiso 1 1 calc R U . . .
O1S O 0.36965(16) 0.74847(13) 0.29563(10) 0.0416(3) Uani 1 1 d . . . . .
O2S O 0.6448(2) 0.89557(15) 0.27622(11) 0.0577(5) Uani 1 1 d . . . . .
C1S C 0.4433(3) 0.8378(2) 0.37922(16) 0.0470(5) Uani 1 1 d . . . . .
H1SA H 0.429882 0.808966 0.446717 0.056 Uiso 1 1 calc R U . . .
H1SB H 0.388606 0.918300 0.376570 0.056 Uiso 1 1 calc R U . . .
C2S C 0.6210(3) 0.8572(3) 0.37304(16) 0.0636(8) Uani 1 1 d . . . . .
H2SA H 0.670612 0.921769 0.431458 0.076 Uiso 1 1 calc R U . . .
H2SB H 0.676918 0.778018 0.380651 0.076 Uiso 1 1 calc R U . . .
C3S C 0.5700(2) 0.80763(19) 0.19207(14) 0.0378(4) Uani 1 1 d . . . . .
H3SA H 0.624470 0.726925 0.193451 0.045 Uiso 1 1 calc R U . . .
H3SB H 0.582880 0.837732 0.124961 0.045 Uiso 1 1 calc R U . . .
C4S C 0.3925(3) 0.7882(2) 0.19866(15) 0.0448(5) Uani 1 1 d . . . . .
H4SA H 0.336556 0.867483 0.191893 0.054 Uiso 1 1 calc R U . . .
H4SB H 0.342425 0.724104 0.139951 0.054 Uiso 1 1 calc R U . . .


_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 C2 1.2280(17) . ?
O2 C4 1.2277(17) . ?
N1 C2 1.3584(19) . ?
N1 C1 1.4366(18) . ?
N1 H1N 0.87(2) . ?
N2 C2 1.3552(18) . ?
N2 C17 1.4584(18) . ?
N2 C3 1.4605(18) . ?
N3 C4 1.3679(18) . ?
N3 C3 1.4453(17) . ?
N3 C19 1.4647(18) . ?
N4 C4 1.3562(18) . ?
N4 C1 1.4545(17) . ?
N4 H4N 0.900(19) . ?
C1 C5 1.511(2) . ?
C1 C3 1.5904(19) . ?
C3 C11 1.5117(19) . ?
C5 C10 1.384(2) . ?
C5 C6 1.389(2) . ?
C6 C7 1.387(2) . ?
C6 H6A 0.9500 . ?
C7 C8 1.376(2) . ?
C7 H7A 0.9500 . ?
C8 C9 1.377(2) . ?
C8 H8A 0.9500 . ?
C9 C10 1.381(2) . ?
C9 H9A 0.9500 . ?
C10 H10A 0.9500 . ?
C11 C16 1.389(2) . ?
C11 C12 1.387(2) . ?
C12 C13 1.385(2) . ?
C12 H12A 0.9500 . ?
C13 C14 1.377(2) . ?
C13 H13A 0.9500 . ?
C14 C15 1.386(2) . ?
C14 H14A 0.9500 . ?
C15 C16 1.381(2) . ?
C15 H15A 0.9500 . ?
C16 H16A 0.9500 . ?
C17 C18 1.513(2) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 C20 1.516(2) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
O1S C1S 1.404(2) . ?
O1S C4S 1.421(2) . ?
O2S C3S 1.403(2) . ?
O2S C2S 1.415(2) . ?
C1S C2S 1.487(3) . ?
C1S H1SA 0.9900 . ?
C1S H1SB 0.9900 . ?
C2S H2SA 0.9900 . ?
C2S H2SB 0.9900 . ?
C3S C4S 1.487(3) . ?
C3S H3SA 0.9900 . ?
C3S H3SB 0.9900 . ?
C4S H4SA 0.9900 . ?
C4S H4SB 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C1 111.37(12) . . ?
C2 N1 H1N 120.5(13) . . ?
C1 N1 H1N 125.3(13) . . ?
C2 N2 C17 122.47(12) . . ?
C2 N2 C3 112.19(11) . . ?
C17 N2 C3 124.53(11) . . ?
C4 N3 C3 110.33(11) . . ?
C4 N3 C19 120.81(12) . . ?
C3 N3 C19 124.65(11) . . ?
C4 N4 C1 112.45(11) . . ?
C4 N4 H4N 120.2(12) . . ?
C1 N4 H4N 122.7(12) . . ?
N1 C1 N4 113.06(11) . . ?
N1 C1 C5 113.09(12) . . ?
N4 C1 C5 112.81(11) . . ?
N1 C1 C3 101.57(11) . . ?
N4 C1 C3 99.84(10) . . ?
C5 C1 C3 115.31(11) . . ?
O1 C2 N2 125.26(14) . . ?
O1 C2 N1 126.06(14) . . ?
N2 C2 N1 108.68(12) . . ?
N3 C3 N2 113.52(11) . . ?
N3 C3 C11 113.72(11) . . ?
N2 C3 C11 112.04(11) . . ?
N3 C3 C1 101.66(10) . . ?
N2 C3 C1 99.65(10) . . ?
C11 C3 C1 115.08(11) . . ?
O2 C4 N4 126.34(13) . . ?
O2 C4 N3 124.85(13) . . ?
N4 C4 N3 108.81(12) . . ?
C10 C5 C6 119.00(14) . . ?
C10 C5 C1 120.40(13) . . ?
C6 C5 C1 120.52(13) . . ?
C7 C6 C5 119.90(15) . . ?
C7 C6 H6A 120.1 . . ?
C5 C6 H6A 120.1 . . ?
C8 C7 C6 120.46(16) . . ?
C8 C7 H7A 119.8 . . ?
C6 C7 H7A 119.8 . . ?
C9 C8 C7 119.85(15) . . ?
C9 C8 H8A 120.1 . . ?
C7 C8 H8A 120.1 . . ?
C8 C9 C10 119.93(16) . . ?
C8 C9 H9A 120.0 . . ?
C10 C9 H9A 120.0 . . ?
C5 C10 C9 120.81(15) . . ?
C5 C10 H10A 119.6 . . ?
C9 C10 H10A 119.6 . . ?
C16 C11 C12 118.88(13) . . ?
C16 C11 C3 121.04(13) . . ?
C12 C11 C3 119.96(13) . . ?
C11 C12 C13 120.20(14) . . ?
C11 C12 H12A 119.9 . . ?
C13 C12 H12A 119.9 . . ?
C14 C13 C12 120.79(14) . . ?
C14 C13 H13A 119.6 . . ?
C12 C13 H13A 119.6 . . ?
C13 C14 C15 119.22(14) . . ?
C13 C14 H14A 120.4 . . ?
C15 C14 H14A 120.4 . . ?
C16 C15 C14 120.27(14) . . ?
C16 C15 H15A 119.9 . . ?
C14 C15 H15A 119.9 . . ?
C11 C16 C15 120.63(14) . . ?
C11 C16 H16A 119.7 . . ?
C15 C16 H16A 119.7 . . ?
N2 C17 C18 111.86(12) . . ?
N2 C17 H17A 109.2 . . ?
C18 C17 H17A 109.2 . . ?
N2 C17 H17B 109.2 . . ?
C18 C17 H17B 109.2 . . ?
H17A C17 H17B 107.9 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N3 C19 C20 112.07(12) . . ?
N3 C19 H19A 109.2 . . ?
C20 C19 H19A 109.2 . . ?
N3 C19 H19B 109.2 . . ?
C20 C19 H19B 109.2 . . ?
H19A C19 H19B 107.9 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C1S O1S C4S 109.69(15) . . ?
C3S O2S C2S 110.44(16) . . ?
O1S C1S C2S 110.39(18) . . ?
O1S C1S H1SA 109.6 . . ?
C2S C1S H1SA 109.6 . . ?
O1S C1S H1SB 109.6 . . ?
C2S C1S H1SB 109.6 . . ?
H1SA C1S H1SB 108.1 . . ?
O2S C2S C1S 111.05(19) . . ?
O2S C2S H2SA 109.4 . . ?
C1S C2S H2SA 109.4 . . ?
O2S C2S H2SB 109.4 . . ?
C1S C2S H2SB 109.4 . . ?
H2SA C2S H2SB 108.0 . . ?
O2S C3S C4S 110.56(17) . . ?
O2S C3S H3SA 109.5 . . ?
C4S C3S H3SA 109.5 . . ?
O2S C3S H3SB 109.5 . . ?
C4S C3S H3SB 109.5 . . ?
H3SA C3S H3SB 108.1 . . ?
O1S C4S C3S 110.92(16) . . ?
O1S C4S H4SA 109.5 . . ?
C3S C4S H4SA 109.5 . . ?
O1S C4S H4SB 109.5 . . ?
C3S C4S H4SB 109.5 . . ?
H4SA C4S H4SB 108.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 N1 C1 N4 -83.08(14) . . . . ?
C2 N1 C1 C5 147.16(12) . . . . ?
C2 N1 C1 C3 22.99(14) . . . . ?
C4 N4 C1 N1 125.41(13) . . . . ?
C4 N4 C1 C5 -104.69(14) . . . . ?
C4 N4 C1 C3 18.24(14) . . . . ?
C17 N2 C2 O1 3.0(2) . . . . ?
C3 N2 C2 O1 173.14(13) . . . . ?
C17 N2 C2 N1 -176.47(12) . . . . ?
C3 N2 C2 N1 -6.34(16) . . . . ?
C1 N1 C2 O1 168.60(13) . . . . ?
C1 N1 C2 N2 -11.93(16) . . . . ?
C4 N3 C3 N2 -81.51(14) . . . . ?
C19 N3 C3 N2 75.41(16) . . . . ?
C4 N3 C3 C11 148.83(12) . . . . ?
C19 N3 C3 C11 -54.26(18) . . . . ?
C4 N3 C3 C1 24.54(14) . . . . ?
C19 N3 C3 C1 -178.55(12) . . . . ?
C2 N2 C3 N3 126.60(12) . . . . ?
C17 N2 C3 N3 -63.51(16) . . . . ?
C2 N2 C3 C11 -102.89(13) . . . . ?
C17 N2 C3 C11 67.00(17) . . . . ?
C2 N2 C3 C1 19.30(14) . . . . ?
C17 N2 C3 C1 -170.82(12) . . . . ?
N1 C1 C3 N3 -140.67(11) . . . . ?
N4 C1 C3 N3 -24.48(13) . . . . ?
C5 C1 C3 N3 96.67(13) . . . . ?
N1 C1 C3 N2 -24.03(12) . . . . ?
N4 C1 C3 N2 92.16(11) . . . . ?
C5 C1 C3 N2 -146.69(11) . . . . ?
N1 C1 C3 C11 95.95(13) . . . . ?
N4 C1 C3 C11 -147.86(12) . . . . ?
C5 C1 C3 C11 -26.71(16) . . . . ?
C1 N4 C4 O2 175.69(14) . . . . ?
C1 N4 C4 N3 -4.10(16) . . . . ?
C3 N3 C4 O2 165.91(14) . . . . ?
C19 N3 C4 O2 8.0(2) . . . . ?
C3 N3 C4 N4 -14.30(16) . . . . ?
C19 N3 C4 N4 -172.24(12) . . . . ?
N1 C1 C5 C10 160.87(13) . . . . ?
N4 C1 C5 C10 30.99(18) . . . . ?
C3 C1 C5 C10 -82.84(16) . . . . ?
N1 C1 C5 C6 -22.29(18) . . . . ?
N4 C1 C5 C6 -152.18(13) . . . . ?
C3 C1 C5 C6 93.99(16) . . . . ?
C10 C5 C6 C7 -0.6(2) . . . . ?
C1 C5 C6 C7 -177.44(14) . . . . ?
C5 C6 C7 C8 2.0(2) . . . . ?
C6 C7 C8 C9 -1.4(3) . . . . ?
C7 C8 C9 C10 -0.6(3) . . . . ?
C6 C5 C10 C9 -1.4(2) . . . . ?
C1 C5 C10 C9 175.44(14) . . . . ?
C8 C9 C10 C5 2.1(2) . . . . ?
N3 C3 C11 C16 -32.98(18) . . . . ?
N2 C3 C11 C16 -163.39(12) . . . . ?
C1 C3 C11 C16 83.72(16) . . . . ?
N3 C3 C11 C12 151.01(13) . . . . ?
N2 C3 C11 C12 20.61(18) . . . . ?
C1 C3 C11 C12 -92.29(16) . . . . ?
C16 C11 C12 C13 0.7(2) . . . . ?
C3 C11 C12 C13 176.79(14) . . . . ?
C11 C12 C13 C14 -0.1(2) . . . . ?
C12 C13 C14 C15 -0.4(2) . . . . ?
C13 C14 C15 C16 0.3(2) . . . . ?
C12 C11 C16 C15 -0.8(2) . . . . ?
C3 C11 C16 C15 -176.85(13) . . . . ?
C14 C15 C16 C11 0.3(2) . . . . ?
C2 N2 C17 C18 -85.47(16) . . . . ?
C3 N2 C17 C18 105.64(15) . . . . ?
C4 N3 C19 C20 -71.79(17) . . . . ?
C3 N3 C19 C20 133.55(14) . . . . ?
C4S O1S C1S C2S -57.7(2) . . . . ?
C3S O2S C2S C1S -56.8(3) . . . . ?
O1S C1S C2S O2S 57.8(3) . . . . ?
C2S O2S C3S C4S 56.4(3) . . . . ?
C1S O1S C4S C3S 57.9(2) . . . . ?
O2S C3S C4S O1S -57.5(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
N1 H1N O1 0.87(2) 1.97(2) 2.8275(16) 168.3(18) 2_677
N4 H4N O2 0.900(19) 1.939(19) 2.8260(16) 168.0(17) 2_667

_refine_diff_density_max         0.422
_refine_diff_density_min         -0.262
_refine_diff_density_rms         0.052



####################################################################### 
# 
# 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_1b-MeOH
_database_code_depnum_ccdc_archive 'CCDC 2072852'
loop_
_audit_author_name
_audit_author_address
'Valentina Karnoukhova'
;A N Nesmeyanov Institute of Organoelement Compounds of Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2021-03-24 deposited with the CCDC.	2021-05-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H22 N4 O2, C H4 O'
_chemical_formula_sum            'C21 H26 N4 O3'
_chemical_formula_weight         382.46

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.7245(7)
_cell_length_b                   9.4309(5)
_cell_length_c                   17.0038(9)
_cell_angle_alpha                90
_cell_angle_beta                 100.2190(10)
_cell_angle_gamma                90
_cell_volume                     2008.15(19)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    262
_cell_measurement_theta_min      3
_cell_measurement_theta_max      25

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.265
_exptl_crystal_F_000             816
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.350
_exptl_crystal_size_mid          0.050
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.086
_shelx_estimated_absorpt_T_min   0.970
_shelx_estimated_absorpt_T_max   0.996
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6258
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX DUO diffractometer'
_diffrn_detector_type            'Bruker APEX II CCD area detector'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            26222
_diffrn_reflns_av_unetI/netI     0.0460
_diffrn_reflns_av_R_equivalents  0.0565
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.434
_diffrn_reflns_theta_max         29.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             5856
_reflns_number_gt                4144
_reflns_threshold_expression     I>2σ(I)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015b)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0518P)²+0.6935P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5856
_refine_ls_number_parameters     268
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0750
_refine_ls_R_factor_gt           0.0459
_refine_ls_wR_factor_ref         0.1213
_refine_ls_wR_factor_gt          0.1053
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_restrained_S_all      1.014
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.58385(8) 1.10001(10) 0.18531(6) 0.0200(2) Uani 1 1 d . . . . .
O2 O 0.50218(8) 0.51506(11) 0.13348(6) 0.0208(2) Uani 1 1 d . . . . .
N1 N 0.60160(9) 0.88487(12) 0.25077(7) 0.0160(2) Uani 1 1 d . . . . .
H1N H 0.5712(15) 0.914(2) 0.2906(12) 0.036(5) Uiso 1 1 d . . . . .
N2 N 0.69580(9) 0.92310(12) 0.15451(6) 0.0154(2) Uani 1 1 d . . . . .
N3 N 0.62792(9) 0.68434(12) 0.11940(6) 0.0156(2) Uani 1 1 d . . . . .
N4 N 0.60371(9) 0.62852(12) 0.24234(7) 0.0161(2) Uani 1 1 d . . . . .
H4N H 0.5554(16) 0.614(2) 0.2738(11) 0.035(5) Uiso 1 1 d . . . . .
C1 C 0.66670(10) 0.75718(14) 0.25356(7) 0.0140(2) Uani 1 1 d . . . . .
C2 C 0.62309(10) 0.97987(14) 0.19616(8) 0.0158(3) Uani 1 1 d . . . . .
C3 C 0.70795(10) 0.77147(14) 0.17023(7) 0.0139(2) Uani 1 1 d . . . . .
C4 C 0.57087(10) 0.60207(14) 0.16195(8) 0.0164(3) Uani 1 1 d . . . . .
C5 C 0.75301(10) 0.74905(15) 0.32778(7) 0.0158(3) Uani 1 1 d . . . . .
C6 C 0.78262(11) 0.86858(15) 0.37464(8) 0.0191(3) Uani 1 1 d . . . . .
H6A H 0.747455 0.956340 0.360941 0.023 Uiso 1 1 calc R U . . .
C7 C 0.86363(12) 0.86016(17) 0.44158(8) 0.0247(3) Uani 1 1 d . . . . .
H7A H 0.883379 0.942181 0.473190 0.030 Uiso 1 1 calc R U . . .
C8 C 0.91531(12) 0.73274(18) 0.46210(9) 0.0279(3) Uani 1 1 d . . . . .
H8A H 0.970177 0.727020 0.507840 0.033 Uiso 1 1 calc R U . . .
C9 C 0.88640(13) 0.61303(18) 0.41531(9) 0.0275(3) Uani 1 1 d . . . . .
H9A H 0.922024 0.525586 0.429053 0.033 Uiso 1 1 calc R U . . .
C10 C 0.80556(11) 0.62075(16) 0.34849(8) 0.0207(3) Uani 1 1 d . . . . .
H10A H 0.786113 0.538596 0.316928 0.025 Uiso 1 1 calc R U . . .
C11 C 0.82103(10) 0.72035(14) 0.17007(7) 0.0150(3) Uani 1 1 d . . . . .
C12 C 0.90737(11) 0.81039(15) 0.19503(8) 0.0182(3) Uani 1 1 d . . . . .
H12A H 0.894965 0.904729 0.210713 0.022 Uiso 1 1 calc R U . . .
C13 C 1.01153(11) 0.76355(16) 0.19721(8) 0.0216(3) Uani 1 1 d . . . . .
H13A H 1.069899 0.825888 0.213815 0.026 Uiso 1 1 calc R U . . .
C14 C 1.02977(11) 0.62536(17) 0.17503(8) 0.0229(3) Uani 1 1 d . . . . .
H14A H 1.100726 0.593446 0.175657 0.028 Uiso 1 1 calc R U . . .
C15 C 0.94481(12) 0.53395(16) 0.15200(8) 0.0222(3) Uani 1 1 d . . . . .
H15A H 0.957744 0.438875 0.137897 0.027 Uiso 1 1 calc R U . . .
C16 C 0.84033(11) 0.58073(15) 0.14939(8) 0.0190(3) Uani 1 1 d . . . . .
H16A H 0.782268 0.517583 0.133546 0.023 Uiso 1 1 calc R U . . .
C17 C 0.72365(11) 0.99565(15) 0.08432(8) 0.0194(3) Uani 1 1 d . . . . .
H17A H 0.657088 1.019080 0.046888 0.023 Uiso 1 1 calc R U . . .
H17B H 0.765511 0.929953 0.056530 0.023 Uiso 1 1 calc R U . . .
C18 C 0.78773(14) 1.13097(17) 0.10495(10) 0.0294(3) Uani 1 1 d . . . . .
H18A H 0.803964 1.173615 0.055928 0.044 Uiso 1 1 calc R U . . .
H18B H 0.854490 1.108555 0.141193 0.044 Uiso 1 1 calc R U . . .
H18C H 0.745994 1.197896 0.131020 0.044 Uiso 1 1 calc R U . . .
C19 C 0.61542(11) 0.67236(15) 0.03222(7) 0.0187(3) Uani 1 1 d . . . . .
H19A H 0.606336 0.571255 0.016859 0.022 Uiso 1 1 calc R U . . .
H19B H 0.681168 0.707158 0.015008 0.022 Uiso 1 1 calc R U . . .
C20 C 0.52062(13) 0.75583(17) -0.01076(9) 0.0282(3) Uani 1 1 d . . . . .
H20A H 0.517674 0.748602 -0.068606 0.042 Uiso 1 1 calc R U . . .
H20B H 0.528141 0.855567 0.005439 0.042 Uiso 1 1 calc R U . . .
H20C H 0.454729 0.717309 0.003086 0.042 Uiso 1 1 calc R U . . .
O1S O 0.27578(10) 0.77519(15) 0.20569(9) 0.0444(3) Uani 1 1 d . . . . .
H1S H 0.331(2) 0.738(3) 0.2423(17) 0.079(9) Uiso 1 1 d . . . . .
C1S C 0.31662(17) 0.7894(2) 0.13410(12) 0.0442(5) Uani 1 1 d . . . . .
H1SC H 0.378913 0.852246 0.143132 0.066 Uiso 1 1 calc R U . . .
H1SB H 0.261525 0.829700 0.092510 0.066 Uiso 1 1 calc R U . . .
H1SA H 0.337756 0.695986 0.116981 0.066 Uiso 1 1 calc R U . . .


_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 C2 1.2387(16) . ?
O2 C4 1.2336(16) . ?
N1 C2 1.3527(17) . ?
N1 C1 1.4576(17) . ?
N1 H1N 0.88(2) . ?
N2 C2 1.3698(16) . ?
N2 C3 1.4579(17) . ?
N2 C17 1.4725(16) . ?
N3 C4 1.3560(17) . ?
N3 C3 1.4652(17) . ?
N3 C19 1.4669(16) . ?
N4 C4 1.3793(17) . ?
N4 C1 1.4481(17) . ?
N4 H4N 0.89(2) . ?
C1 C5 1.5209(18) . ?
C1 C3 1.6017(17) . ?
C3 C11 1.5179(17) . ?
C5 C6 1.3931(19) . ?
C5 C10 1.3970(19) . ?
C6 C7 1.396(2) . ?
C6 H6A 0.9500 . ?
C7 C8 1.384(2) . ?
C7 H7A 0.9500 . ?
C8 C9 1.393(2) . ?
C8 H8A 0.9500 . ?
C9 C10 1.393(2) . ?
C9 H9A 0.9500 . ?
C10 H10A 0.9500 . ?
C11 C12 1.3939(19) . ?
C11 C16 1.3959(19) . ?
C12 C13 1.3913(19) . ?
C12 H12A 0.9500 . ?
C13 C14 1.388(2) . ?
C13 H13A 0.9500 . ?
C14 C15 1.384(2) . ?
C14 H14A 0.9500 . ?
C15 C16 1.3939(19) . ?
C15 H15A 0.9500 . ?
C16 H16A 0.9500 . ?
C17 C18 1.522(2) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 C20 1.515(2) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
O1S C1S 1.412(2) . ?
O1S H1S 0.92(3) . ?
C1S H1SC 0.9800 . ?
C1S H1SB 0.9800 . ?
C1S H1SA 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
C2 N1 C1 112.74(10) . . ?
C2 N1 H1N 119.2(12) . . ?
C1 N1 H1N 124.0(12) . . ?
C2 N2 C3 110.37(10) . . ?
C2 N2 C17 121.27(11) . . ?
C3 N2 C17 124.84(11) . . ?
C4 N3 C3 112.83(10) . . ?
C4 N3 C19 121.52(11) . . ?
C3 N3 C19 125.36(11) . . ?
C4 N4 C1 110.20(10) . . ?
C4 N4 H4N 116.5(12) . . ?
C1 N4 H4N 118.2(12) . . ?
N4 C1 N1 112.95(10) . . ?
N4 C1 C5 111.62(11) . . ?
N1 C1 C5 113.03(11) . . ?
N4 C1 C3 102.39(10) . . ?
N1 C1 C3 100.09(10) . . ?
C5 C1 C3 115.89(10) . . ?
O1 C2 N1 125.65(12) . . ?
O1 C2 N2 124.88(12) . . ?
N1 C2 N2 109.47(11) . . ?
N2 C3 N3 113.70(10) . . ?
N2 C3 C11 112.39(10) . . ?
N3 C3 C11 112.38(11) . . ?
N2 C3 C1 101.77(10) . . ?
N3 C3 C1 99.91(9) . . ?
C11 C3 C1 115.75(10) . . ?
O2 C4 N3 125.47(12) . . ?
O2 C4 N4 125.33(12) . . ?
N3 C4 N4 109.19(11) . . ?
C6 C5 C10 119.20(12) . . ?
C6 C5 C1 121.06(12) . . ?
C10 C5 C1 119.72(12) . . ?
C5 C6 C7 120.40(14) . . ?
C5 C6 H6A 119.8 . . ?
C7 C6 H6A 119.8 . . ?
C8 C7 C6 120.26(14) . . ?
C8 C7 H7A 119.9 . . ?
C6 C7 H7A 119.9 . . ?
C7 C8 C9 119.62(13) . . ?
C7 C8 H8A 120.2 . . ?
C9 C8 H8A 120.2 . . ?
C8 C9 C10 120.38(14) . . ?
C8 C9 H9A 119.8 . . ?
C10 C9 H9A 119.8 . . ?
C9 C10 C5 120.14(14) . . ?
C9 C10 H10A 119.9 . . ?
C5 C10 H10A 119.9 . . ?
C12 C11 C16 119.14(12) . . ?
C12 C11 C3 120.14(12) . . ?
C16 C11 C3 120.62(12) . . ?
C13 C12 C11 120.69(13) . . ?
C13 C12 H12A 119.7 . . ?
C11 C12 H12A 119.7 . . ?
C14 C13 C12 119.70(13) . . ?
C14 C13 H13A 120.2 . . ?
C12 C13 H13A 120.2 . . ?
C15 C14 C13 120.14(13) . . ?
C15 C14 H14A 119.9 . . ?
C13 C14 H14A 119.9 . . ?
C14 C15 C16 120.30(13) . . ?
C14 C15 H15A 119.8 . . ?
C16 C15 H15A 119.8 . . ?
C15 C16 C11 120.00(13) . . ?
C15 C16 H16A 120.0 . . ?
C11 C16 H16A 120.0 . . ?
N2 C17 C18 113.52(11) . . ?
N2 C17 H17A 108.9 . . ?
C18 C17 H17A 108.9 . . ?
N2 C17 H17B 108.9 . . ?
C18 C17 H17B 108.9 . . ?
H17A C17 H17B 107.7 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N3 C19 C20 112.44(12) . . ?
N3 C19 H19A 109.1 . . ?
C20 C19 H19A 109.1 . . ?
N3 C19 H19B 109.1 . . ?
C20 C19 H19B 109.1 . . ?
H19A C19 H19B 107.8 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C1S O1S H1S 105.2(18) . . ?
O1S C1S H1SC 109.5 . . ?
O1S C1S H1SB 109.5 . . ?
H1SC C1S H1SB 109.5 . . ?
O1S C1S H1SA 109.5 . . ?
H1SC C1S H1SA 109.5 . . ?
H1SB C1S H1SA 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
C4 N4 C1 N1 84.15(13) . . . . ?
C4 N4 C1 C5 -147.18(11) . . . . ?
C4 N4 C1 C3 -22.57(13) . . . . ?
C2 N1 C1 N4 -125.11(12) . . . . ?
C2 N1 C1 C5 106.96(12) . . . . ?
C2 N1 C1 C3 -16.92(13) . . . . ?
C1 N1 C2 O1 -175.33(13) . . . . ?
C1 N1 C2 N2 4.38(15) . . . . ?
C3 N2 C2 O1 -168.01(12) . . . . ?
C17 N2 C2 O1 -8.2(2) . . . . ?
C3 N2 C2 N1 12.28(15) . . . . ?
C17 N2 C2 N1 172.08(11) . . . . ?
C2 N2 C3 N3 84.77(13) . . . . ?
C17 N2 C3 N3 -74.16(15) . . . . ?
C2 N2 C3 C11 -146.15(11) . . . . ?
C17 N2 C3 C11 54.93(16) . . . . ?
C2 N2 C3 C1 -21.69(13) . . . . ?
C17 N2 C3 C1 179.38(11) . . . . ?
C4 N3 C3 N2 -122.52(12) . . . . ?
C19 N3 C3 N2 63.67(16) . . . . ?
C4 N3 C3 C11 108.39(12) . . . . ?
C19 N3 C3 C11 -65.42(16) . . . . ?
C4 N3 C3 C1 -14.90(13) . . . . ?
C19 N3 C3 C1 171.30(12) . . . . ?
N4 C1 C3 N2 138.47(10) . . . . ?
N1 C1 C3 N2 22.07(11) . . . . ?
C5 C1 C3 N2 -99.81(12) . . . . ?
N4 C1 C3 N3 21.52(12) . . . . ?
N1 C1 C3 N3 -94.88(11) . . . . ?
C5 C1 C3 N3 143.25(11) . . . . ?
N4 C1 C3 C11 -99.36(12) . . . . ?
N1 C1 C3 C11 144.24(11) . . . . ?
C5 C1 C3 C11 22.36(16) . . . . ?
C3 N3 C4 O2 -176.71(13) . . . . ?
C19 N3 C4 O2 -2.6(2) . . . . ?
C3 N3 C4 N4 1.81(15) . . . . ?
C19 N3 C4 N4 175.88(11) . . . . ?
C1 N4 C4 O2 -167.16(13) . . . . ?
C1 N4 C4 N3 14.32(15) . . . . ?
N4 C1 C5 C6 -144.76(12) . . . . ?
N1 C1 C5 C6 -16.14(16) . . . . ?
C3 C1 C5 C6 98.56(14) . . . . ?
N4 C1 C5 C10 36.84(16) . . . . ?
N1 C1 C5 C10 165.46(11) . . . . ?
C3 C1 C5 C10 -79.83(15) . . . . ?
C10 C5 C6 C7 -0.2(2) . . . . ?
C1 C5 C6 C7 -178.57(12) . . . . ?
C5 C6 C7 C8 -0.1(2) . . . . ?
C6 C7 C8 C9 0.3(2) . . . . ?
C7 C8 C9 C10 -0.4(2) . . . . ?
C8 C9 C10 C5 0.2(2) . . . . ?
C6 C5 C10 C9 0.1(2) . . . . ?
C1 C5 C10 C9 178.53(12) . . . . ?
N2 C3 C11 C12 31.63(16) . . . . ?
N3 C3 C11 C12 161.40(11) . . . . ?
C1 C3 C11 C12 -84.70(15) . . . . ?
N2 C3 C11 C16 -152.03(11) . . . . ?
N3 C3 C11 C16 -22.26(17) . . . . ?
C1 C3 C11 C16 91.64(14) . . . . ?
C16 C11 C12 C13 1.9(2) . . . . ?
C3 C11 C12 C13 178.25(12) . . . . ?
C11 C12 C13 C14 -0.6(2) . . . . ?
C12 C13 C14 C15 -1.0(2) . . . . ?
C13 C14 C15 C16 1.3(2) . . . . ?
C14 C15 C16 C11 0.0(2) . . . . ?
C12 C11 C16 C15 -1.55(19) . . . . ?
C3 C11 C16 C15 -177.92(12) . . . . ?
C2 N2 C17 C18 69.79(16) . . . . ?
C3 N2 C17 C18 -133.44(13) . . . . ?
C4 N3 C19 C20 82.66(16) . . . . ?
C3 N3 C19 C20 -104.04(15) . . . . ?

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
N4 H4N O1 0.89(2) 2.02(2) 2.8850(15) 162.7(17) 2_645
O1S H1S O1 0.92(3) 1.98(3) 2.8601(17) 159(2) 2_645
N1 H1N O2 0.88(2) 1.97(2) 2.8368(15) 168.5(18) 2_655

_refine_diff_density_max         0.357
_refine_diff_density_min         -0.222
_refine_diff_density_rms         0.051



####################################################################### 
# 
# 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_1b-pyr
_database_code_depnum_ccdc_archive 'CCDC 2072851'
loop_
_audit_author_name
_audit_author_address
'Valentina Karnoukhova'
;A N Nesmeyanov Institute of Organoelement Compounds of Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2021-03-24 deposited with the CCDC.	2021-05-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H22 N4 O2, C5 H5 N'
_chemical_formula_sum            'C25 H27 N5 O2'
_chemical_formula_weight         429.51

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   13.2527(11)
_cell_length_b                   13.5955(11)
_cell_length_c                   14.5032(12)
_cell_angle_alpha                112.4997(17)
_cell_angle_beta                 98.1336(17)
_cell_angle_gamma                104.9098(18)
_cell_volume                     2247.1(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    962
_cell_measurement_theta_min      3
_cell_measurement_theta_max      25

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.270
_exptl_crystal_F_000             912
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.390
_exptl_crystal_size_mid          0.350
_exptl_crystal_size_min          0.320
_exptl_absorpt_coefficient_mu    0.083
_shelx_estimated_absorpt_T_min   0.968
_shelx_estimated_absorpt_T_max   0.974
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6736
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX DUO diffractometer'
_diffrn_detector_type            'Bruker APEX II CCD area detector'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            30094
_diffrn_reflns_av_unetI/netI     0.0546
_diffrn_reflns_av_R_equivalents  0.0376
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         1.651
_diffrn_reflns_theta_max         30.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             13077
_reflns_number_gt                8879
_reflns_threshold_expression     I>2σ(I)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015b)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0689P)²+0.2249P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         13077
_refine_ls_number_parameters     597
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0831
_refine_ls_R_factor_gt           0.0530
_refine_ls_wR_factor_ref         0.1466
_refine_ls_wR_factor_gt          0.1278
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.88826(8) -0.11010(8) -0.00072(8) 0.0208(2) Uani 1 1 d . . . . .
O2 O 0.63079(8) 0.17062(9) 0.03571(8) 0.0215(2) Uani 1 1 d . . . . .
N1 N 0.93616(9) 0.08433(9) 0.08911(9) 0.0168(2) Uani 1 1 d . . . . .
H1N H 0.9882(16) 0.0979(15) 0.0600(14) 0.032(5) Uiso 1 1 d . . . . .
N2 N 0.78754(9) -0.02575(9) 0.09934(8) 0.0153(2) Uani 1 1 d . . . . .
N3 N 0.70532(9) 0.12039(9) 0.15750(8) 0.0152(2) Uani 1 1 d . . . . .
N4 N 0.80792(9) 0.17637(10) 0.06609(9) 0.0167(2) Uani 1 1 d . . . . .
H4N H 0.8299(15) 0.2159(15) 0.0309(14) 0.030(5) Uiso 1 1 d . . . . .
C1 C 0.88307(10) 0.16177(11) 0.13882(10) 0.0145(2) Uani 1 1 d . . . . .
C2 C 0.87245(10) -0.02494(11) 0.05689(10) 0.0159(3) Uani 1 1 d . . . . .
C3 C 0.79906(10) 0.08720(11) 0.17493(10) 0.0134(2) Uani 1 1 d . . . . .
C4 C 0.70779(11) 0.15733(11) 0.08117(10) 0.0158(3) Uani 1 1 d . . . . .
C5 C 0.96013(11) 0.27225(11) 0.22531(10) 0.0159(3) Uani 1 1 d . . . . .
C6 C 1.05851(11) 0.27733(12) 0.27779(11) 0.0214(3) Uani 1 1 d . . . . .
H6A H 1.080603 0.212772 0.255365 0.026 Uiso 1 1 calc R U . . .
C7 C 1.12481(13) 0.37621(13) 0.36288(12) 0.0271(3) Uani 1 1 d . . . . .
H7A H 1.192767 0.379543 0.397853 0.032 Uiso 1 1 calc R U . . .
C8 C 1.09281(13) 0.46984(13) 0.39715(12) 0.0283(3) Uani 1 1 d . . . . .
H8A H 1.137853 0.536916 0.456485 0.034 Uiso 1 1 calc R U . . .
C9 C 0.99522(13) 0.46589(12) 0.34507(12) 0.0258(3) Uani 1 1 d . . . . .
H9A H 0.973085 0.530373 0.368422 0.031 Uiso 1 1 calc R U . . .
C10 C 0.92937(12) 0.36774(12) 0.25856(11) 0.0208(3) Uani 1 1 d . . . . .
H10A H 0.862977 0.365786 0.221890 0.025 Uiso 1 1 calc R U . . .
C11 C 0.84041(10) 0.10488(11) 0.28479(10) 0.0155(3) Uani 1 1 d . . . . .
C12 C 0.89750(12) 0.03871(12) 0.30360(11) 0.0209(3) Uani 1 1 d . . . . .
H12A H 0.903037 -0.022839 0.246995 0.025 Uiso 1 1 calc R U . . .
C13 C 0.94627(13) 0.06164(14) 0.40389(12) 0.0277(3) Uani 1 1 d . . . . .
H13A H 0.985436 0.016171 0.415768 0.033 Uiso 1 1 calc R U . . .
C14 C 0.93816(13) 0.15062(13) 0.48693(11) 0.0260(3) Uani 1 1 d . . . . .
H14A H 0.972093 0.166724 0.555796 0.031 Uiso 1 1 calc R U . . .
C15 C 0.88048(12) 0.21587(12) 0.46915(11) 0.0216(3) Uani 1 1 d . . . . .
H15A H 0.873902 0.276401 0.526002 0.026 Uiso 1 1 calc R U . . .
C16 C 0.83222(11) 0.19348(11) 0.36888(10) 0.0176(3) Uani 1 1 d . . . . .
H16A H 0.793076 0.239141 0.357417 0.021 Uiso 1 1 calc R U . . .
C17 C 0.70688(11) -0.13034(11) 0.08433(10) 0.0173(3) Uani 1 1 d . . . . .
H17A H 0.676114 -0.115527 0.144635 0.021 Uiso 1 1 calc R U . . .
H17B H 0.742301 -0.187157 0.080255 0.021 Uiso 1 1 calc R U . . .
C18 C 0.61628(12) -0.17744(13) -0.01362(12) 0.0258(3) Uani 1 1 d . . . . .
H18A H 0.561367 -0.244923 -0.019235 0.039 Uiso 1 1 calc R U . . .
H18B H 0.645728 -0.197756 -0.073911 0.039 Uiso 1 1 calc R U . . .
H18C H 0.583138 -0.120116 -0.011071 0.039 Uiso 1 1 calc R U . . .
C19 C 0.60281(11) 0.07519(12) 0.17802(11) 0.0197(3) Uani 1 1 d . . . . .
H19A H 0.613858 0.035137 0.220940 0.024 Uiso 1 1 calc R U . . .
H19B H 0.548923 0.019513 0.111597 0.024 Uiso 1 1 calc R U . . .
C20 C 0.55869(13) 0.16759(14) 0.23355(12) 0.0257(3) Uani 1 1 d . . . . .
H20A H 0.491384 0.134131 0.247797 0.039 Uiso 1 1 calc R U . . .
H20B H 0.544029 0.204850 0.189733 0.039 Uiso 1 1 calc R U . . .
H20C H 0.612167 0.223419 0.298975 0.039 Uiso 1 1 calc R U . . .
O1A O 0.37685(8) 0.39390(8) -0.01156(8) 0.0236(2) Uani 1 1 d . . . . .
O2A O 0.15187(8) 0.70715(9) 0.05489(8) 0.0250(2) Uani 1 1 d . . . . .
N1A N 0.43819(9) 0.58747(10) 0.08692(9) 0.0184(2) Uani 1 1 d . . . . .
H1NA H 0.4957(16) 0.6018(16) 0.0630(14) 0.038(5) Uiso 1 1 d . . . . .
N2A N 0.28551(9) 0.48367(9) 0.09700(9) 0.0164(2) Uani 1 1 d . . . . .
N3A N 0.21646(9) 0.63897(10) 0.16479(9) 0.0162(2) Uani 1 1 d . . . . .
N4A N 0.32448(9) 0.69844(10) 0.07916(9) 0.0178(2) Uani 1 1 d . . . . .
H4NA H 0.3508(14) 0.7412(14) 0.0505(13) 0.022(4) Uiso 1 1 d . . . . .
C1A C 0.39409(10) 0.66971(11) 0.14460(10) 0.0149(3) Uani 1 1 d . . . . .
C2A C 0.36777(11) 0.48033(12) 0.05103(11) 0.0177(3) Uani 1 1 d . . . . .
C3A C 0.30469(10) 0.59661(11) 0.17761(10) 0.0146(3) Uani 1 1 d . . . . .
C4A C 0.22446(11) 0.68379(12) 0.09487(10) 0.0179(3) Uani 1 1 d . . . . .
C5A C 0.47935(11) 0.77347(11) 0.23225(10) 0.0175(3) Uani 1 1 d . . . . .
C6A C 0.58038(12) 0.77096(13) 0.27057(11) 0.0242(3) Uani 1 1 d . . . . .
H6AA H 0.597098 0.703590 0.241003 0.029 Uiso 1 1 calc R U . . .
C7A C 0.65698(13) 0.86700(15) 0.35216(13) 0.0333(4) Uani 1 1 d . . . . .
H7AA H 0.726616 0.865657 0.377141 0.040 Uiso 1 1 calc R U . . .
C8A C 0.63229(15) 0.96449(14) 0.39713(13) 0.0363(4) Uani 1 1 d . . . . .
H8AA H 0.684756 1.029892 0.453078 0.044 Uiso 1 1 calc R U . . .
C9A C 0.53154(15) 0.96663(13) 0.36071(12) 0.0334(4) Uani 1 1 d . . . . .
H9AA H 0.513927 1.033021 0.392578 0.040 Uiso 1 1 calc R U . . .
C10A C 0.45579(13) 0.87213(12) 0.27765(11) 0.0242(3) Uani 1 1 d . . . . .
H10B H 0.387160 0.874852 0.251543 0.029 Uiso 1 1 calc R U . . .
C11A C 0.33801(10) 0.60522(11) 0.28538(10) 0.0154(3) Uani 1 1 d . . . . .
C12A C 0.37535(11) 0.52422(12) 0.30042(11) 0.0206(3) Uani 1 1 d . . . . .
H12B H 0.379304 0.462835 0.242556 0.025 Uiso 1 1 calc R U . . .
C13A C 0.40683(13) 0.53246(13) 0.39930(12) 0.0258(3) Uani 1 1 d . . . . .
H13B H 0.431132 0.476149 0.408672 0.031 Uiso 1 1 calc R U . . .
C14A C 0.40294(12) 0.62229(13) 0.48408(11) 0.0249(3) Uani 1 1 d . . . . .
H14B H 0.424955 0.628244 0.551812 0.030 Uiso 1 1 calc R U . . .
C15A C 0.36680(12) 0.70347(12) 0.46974(11) 0.0223(3) Uani 1 1 d . . . . .
H15B H 0.364301 0.765524 0.527935 0.027 Uiso 1 1 calc R U . . .
C16A C 0.33423(11) 0.69505(12) 0.37127(10) 0.0182(3) Uani 1 1 d . . . . .
H16B H 0.309095 0.751094 0.362314 0.022 Uiso 1 1 calc R U . . .
C17A C 0.19940(11) 0.38075(12) 0.07860(11) 0.0188(3) Uani 1 1 d . . . . .
H17C H 0.166950 0.396317 0.137846 0.023 Uiso 1 1 calc R U . . .
H17D H 0.230910 0.321024 0.074194 0.023 Uiso 1 1 calc R U . . .
C18A C 0.11173(12) 0.33850(13) -0.02007(12) 0.0278(3) Uani 1 1 d . . . . .
H18D H 0.054153 0.271554 -0.028117 0.042 Uiso 1 1 calc R U . . .
H18E H 0.142680 0.318480 -0.079384 0.042 Uiso 1 1 calc R U . . .
H18F H 0.081535 0.398067 -0.016679 0.042 Uiso 1 1 calc R U . . .
C19A C 0.11282(11) 0.59974(12) 0.18592(11) 0.0200(3) Uani 1 1 d . . . . .
H19C H 0.119622 0.556506 0.226631 0.024 Uiso 1 1 calc R U . . .
H19D H 0.057079 0.548054 0.119538 0.024 Uiso 1 1 calc R U . . .
C20A C 0.07629(12) 0.69732(14) 0.24534(12) 0.0255(3) Uani 1 1 d . . . . .
H20D H 0.008419 0.667790 0.260786 0.038 Uiso 1 1 calc R U . . .
H20E H 0.064736 0.737280 0.203292 0.038 Uiso 1 1 calc R U . . .
H20F H 0.132158 0.749803 0.310250 0.038 Uiso 1 1 calc R U . . .
N1S N 0.81836(13) 0.63880(16) 0.30342(14) 0.0499(4) Uani 1 1 d . . . . .
C1S C 0.76296(17) 0.54792(19) 0.21309(16) 0.0481(5) Uani 1 1 d . . . . .
H1SA H 0.790250 0.539644 0.154413 0.058 Uiso 1 1 calc R U . . .
C2S C 0.66981(16) 0.46690(17) 0.20085(15) 0.0426(5) Uani 1 1 d . . . . .
H2SA H 0.634245 0.403318 0.135629 0.051 Uiso 1 1 calc R U . . .
C3S C 0.62851(15) 0.47882(15) 0.28409(14) 0.0374(4) Uani 1 1 d . . . . .
H3SA H 0.563337 0.423991 0.277591 0.045 Uiso 1 1 calc R U . . .
C4S C 0.68287(15) 0.57153(16) 0.37749(14) 0.0373(4) Uani 1 1 d . . . . .
H4SA H 0.655760 0.582598 0.436585 0.045 Uiso 1 1 calc R U . . .
C5S C 0.77733(15) 0.64766(17) 0.38308(15) 0.0409(4) Uani 1 1 d . . . . .
H5SA H 0.815573 0.710540 0.448149 0.049 Uiso 1 1 calc R U . . .
N1SA N 0.33088(13) 0.23663(13) 0.36376(12) 0.0384(4) Uani 1 1 d . . . . .
C1SA C 0.28117(15) 0.18874(17) 0.26340(15) 0.0388(4) Uani 1 1 d . . . . .
H1SB H 0.280525 0.236636 0.229967 0.047 Uiso 1 1 calc R U . . .
C2SA C 0.23060(17) 0.07419(18) 0.20485(14) 0.0452(5) Uani 1 1 d . . . . .
H2SB H 0.196741 0.044349 0.132989 0.054 Uiso 1 1 calc R U . . .
C3SA C 0.22971(19) 0.00394(18) 0.25141(16) 0.0494(5) Uani 1 1 d . . . . .
H3SB H 0.194847 -0.075642 0.213268 0.059 Uiso 1 1 calc R U . . .
C4SA C 0.28114(18) 0.05228(17) 0.35577(15) 0.0472(5) Uani 1 1 d . . . . .
H4SB H 0.282659 0.006437 0.391248 0.057 Uiso 1 1 calc R U . . .
C5SA C 0.32980(17) 0.16710(17) 0.40719(14) 0.0413(4) Uani 1 1 d . . . . .
H5SB H 0.365210 0.199046 0.478933 0.050 Uiso 1 1 calc R U . . .


_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 C2 1.2315(16) . ?
O2 C4 1.2266(16) . ?
N1 C2 1.3600(17) . ?
N1 C1 1.4377(17) . ?
N1 H1N 0.873(19) . ?
N2 C2 1.3566(17) . ?
N2 C17 1.4584(16) . ?
N2 C3 1.4585(16) . ?
N3 C4 1.3805(16) . ?
N3 C3 1.4483(16) . ?
N3 C19 1.4618(17) . ?
N4 C4 1.3508(17) . ?
N4 C1 1.4522(17) . ?
N4 H4N 0.898(19) . ?
C1 C5 1.5096(18) . ?
C1 C3 1.5913(18) . ?
C3 C11 1.5128(18) . ?
C5 C6 1.3844(19) . ?
C5 C10 1.3902(19) . ?
C6 C7 1.385(2) . ?
C6 H6A 0.9500 . ?
C7 C8 1.379(2) . ?
C7 H7A 0.9500 . ?
C8 C9 1.379(2) . ?
C8 H8A 0.9500 . ?
C9 C10 1.388(2) . ?
C9 H9A 0.9500 . ?
C10 H10A 0.9500 . ?
C11 C16 1.3894(19) . ?
C11 C12 1.3913(19) . ?
C12 C13 1.384(2) . ?
C12 H12A 0.9500 . ?
C13 C14 1.383(2) . ?
C13 H13A 0.9500 . ?
C14 C15 1.381(2) . ?
C14 H14A 0.9500 . ?
C15 C16 1.3836(19) . ?
C15 H15A 0.9500 . ?
C16 H16A 0.9500 . ?
C17 C18 1.5150(19) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 C20 1.518(2) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
O1A C2A 1.2274(16) . ?
O2A C4A 1.2258(16) . ?
N1A C2A 1.3588(17) . ?
N1A C1A 1.4319(17) . ?
N1A H1NA 0.89(2) . ?
N2A C2A 1.3575(17) . ?
N2A C3A 1.4595(17) . ?
N2A C17A 1.4622(17) . ?
N3A C4A 1.3714(17) . ?
N3A C3A 1.4493(16) . ?
N3A C19A 1.4602(17) . ?
N4A C4A 1.3540(17) . ?
N4A C1A 1.4581(17) . ?
N4A H4NA 0.869(17) . ?
C1A C5A 1.5111(18) . ?
C1A C3A 1.5934(18) . ?
C3A C11A 1.5132(18) . ?
C5A C10A 1.389(2) . ?
C5A C6A 1.389(2) . ?
C6A C7A 1.390(2) . ?
C6A H6AA 0.9500 . ?
C7A C8A 1.382(3) . ?
C7A H7AA 0.9500 . ?
C8A C9A 1.376(3) . ?
C8A H8AA 0.9500 . ?
C9A C10A 1.385(2) . ?
C9A H9AA 0.9500 . ?
C10A H10B 0.9500 . ?
C11A C16A 1.3894(19) . ?
C11A C12A 1.3924(19) . ?
C12A C13A 1.388(2) . ?
C12A H12B 0.9500 . ?
C13A C14A 1.381(2) . ?
C13A H13B 0.9500 . ?
C14A C15A 1.382(2) . ?
C14A H14B 0.9500 . ?
C15A C16A 1.3834(19) . ?
C15A H15B 0.9500 . ?
C16A H16B 0.9500 . ?
C17A C18A 1.511(2) . ?
C17A H17C 0.9900 . ?
C17A H17D 0.9900 . ?
C18A H18D 0.9800 . ?
C18A H18E 0.9800 . ?
C18A H18F 0.9800 . ?
C19A C20A 1.520(2) . ?
C19A H19C 0.9900 . ?
C19A H19D 0.9900 . ?
C20A H20D 0.9800 . ?
C20A H20E 0.9800 . ?
C20A H20F 0.9800 . ?
N1S C5S 1.323(2) . ?
N1S C1S 1.343(3) . ?
C1S C2S 1.363(3) . ?
C1S H1SA 0.9500 . ?
C2S C3S 1.366(3) . ?
C2S H2SA 0.9500 . ?
C3S C4S 1.376(2) . ?
C3S H3SA 0.9500 . ?
C4S C5S 1.373(3) . ?
C4S H4SA 0.9500 . ?
C5S H5SA 0.9500 . ?
N1SA C5SA 1.320(2) . ?
N1SA C1SA 1.326(2) . ?
C1SA C2SA 1.373(3) . ?
C1SA H1SB 0.9500 . ?
C2SA C3SA 1.363(3) . ?
C2SA H2SB 0.9500 . ?
C3SA C4SA 1.380(3) . ?
C3SA H3SB 0.9500 . ?
C4SA C5SA 1.365(3) . ?
C4SA H4SB 0.9500 . ?
C5SA H5SB 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C1 111.27(11) . . ?
C2 N1 H1N 118.5(12) . . ?
C1 N1 H1N 126.2(12) . . ?
C2 N2 C17 122.48(11) . . ?
C2 N2 C3 111.82(10) . . ?
C17 N2 C3 124.74(11) . . ?
C4 N3 C3 109.55(10) . . ?
C4 N3 C19 120.81(11) . . ?
C3 N3 C19 124.17(11) . . ?
C4 N4 C1 112.56(11) . . ?
C4 N4 H4N 121.5(12) . . ?
C1 N4 H4N 122.8(12) . . ?
N1 C1 N4 113.18(11) . . ?
N1 C1 C5 113.44(11) . . ?
N4 C1 C5 113.36(11) . . ?
N1 C1 C3 101.24(10) . . ?
N4 C1 C3 99.70(10) . . ?
C5 C1 C3 114.57(10) . . ?
O1 C2 N2 124.82(12) . . ?
O1 C2 N1 126.41(12) . . ?
N2 C2 N1 108.77(11) . . ?
N3 C3 N2 113.92(10) . . ?
N3 C3 C11 114.66(11) . . ?
N2 C3 C11 111.74(11) . . ?
N3 C3 C1 101.57(10) . . ?
N2 C3 C1 99.77(10) . . ?
C11 C3 C1 113.83(10) . . ?
O2 C4 N4 126.44(12) . . ?
O2 C4 N3 124.71(12) . . ?
N4 C4 N3 108.85(11) . . ?
C6 C5 C10 119.20(13) . . ?
C6 C5 C1 120.35(12) . . ?
C10 C5 C1 120.25(12) . . ?
C7 C6 C5 120.21(13) . . ?
C7 C6 H6A 119.9 . . ?
C5 C6 H6A 119.9 . . ?
C8 C7 C6 120.40(14) . . ?
C8 C7 H7A 119.8 . . ?
C6 C7 H7A 119.8 . . ?
C7 C8 C9 119.84(14) . . ?
C7 C8 H8A 120.1 . . ?
C9 C8 H8A 120.1 . . ?
C8 C9 C10 120.01(14) . . ?
C8 C9 H9A 120.0 . . ?
C10 C9 H9A 120.0 . . ?
C9 C10 C5 120.30(13) . . ?
C9 C10 H10A 119.9 . . ?
C5 C10 H10A 119.9 . . ?
C16 C11 C12 118.58(12) . . ?
C16 C11 C3 121.35(12) . . ?
C12 C11 C3 119.76(12) . . ?
C13 C12 C11 120.67(13) . . ?
C13 C12 H12A 119.7 . . ?
C11 C12 H12A 119.7 . . ?
C14 C13 C12 120.17(14) . . ?
C14 C13 H13A 119.9 . . ?
C12 C13 H13A 119.9 . . ?
C15 C14 C13 119.62(13) . . ?
C15 C14 H14A 120.2 . . ?
C13 C14 H14A 120.2 . . ?
C14 C15 C16 120.27(14) . . ?
C14 C15 H15A 119.9 . . ?
C16 C15 H15A 119.9 . . ?
C15 C16 C11 120.68(13) . . ?
C15 C16 H16A 119.7 . . ?
C11 C16 H16A 119.7 . . ?
N2 C17 C18 111.50(11) . . ?
N2 C17 H17A 109.3 . . ?
C18 C17 H17A 109.3 . . ?
N2 C17 H17B 109.3 . . ?
C18 C17 H17B 109.3 . . ?
H17A C17 H17B 108.0 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N3 C19 C20 112.09(12) . . ?
N3 C19 H19A 109.2 . . ?
C20 C19 H19A 109.2 . . ?
N3 C19 H19B 109.2 . . ?
C20 C19 H19B 109.2 . . ?
H19A C19 H19B 107.9 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C2A N1A C1A 111.49(11) . . ?
C2A N1A H1NA 121.3(12) . . ?
C1A N1A H1NA 125.6(12) . . ?
C2A N2A C3A 112.05(11) . . ?
C2A N2A C17A 121.99(11) . . ?
C3A N2A C17A 125.10(11) . . ?
C4A N3A C3A 110.16(11) . . ?
C4A N3A C19A 121.00(11) . . ?
C3A N3A C19A 124.35(11) . . ?
C4A N4A C1A 112.64(11) . . ?
C4A N4A H4NA 122.3(11) . . ?
C1A N4A H4NA 121.9(11) . . ?
N1A C1A N4A 113.06(11) . . ?
N1A C1A C5A 112.93(11) . . ?
N4A C1A C5A 112.31(11) . . ?
N1A C1A C3A 101.79(10) . . ?
N4A C1A C3A 99.81(10) . . ?
C5A C1A C3A 115.90(10) . . ?
O1A C2A N2A 125.04(13) . . ?
O1A C2A N1A 126.14(13) . . ?
N2A C2A N1A 108.82(12) . . ?
N3A C3A N2A 113.56(11) . . ?
N3A C3A C11A 112.40(11) . . ?
N2A C3A C11A 112.28(11) . . ?
N3A C3A C1A 101.80(10) . . ?
N2A C3A C1A 99.71(10) . . ?
C11A C3A C1A 116.14(10) . . ?
O2A C4A N4A 126.58(12) . . ?
O2A C4A N3A 124.44(12) . . ?
N4A C4A N3A 108.97(12) . . ?
C10A C5A C6A 119.15(13) . . ?
C10A C5A C1A 119.80(13) . . ?
C6A C5A C1A 121.03(13) . . ?
C5A C6A C7A 119.99(15) . . ?
C5A C6A H6AA 120.0 . . ?
C7A C6A H6AA 120.0 . . ?
C8A C7A C6A 120.30(16) . . ?
C8A C7A H7AA 119.9 . . ?
C6A C7A H7AA 119.9 . . ?
C9A C8A C7A 119.88(15) . . ?
C9A C8A H8AA 120.1 . . ?
C7A C8A H8AA 120.1 . . ?
C8A C9A C10A 120.11(16) . . ?
C8A C9A H9AA 119.9 . . ?
C10A C9A H9AA 119.9 . . ?
C9A C10A C5A 120.54(15) . . ?
C9A C10A H10B 119.7 . . ?
C5A C10A H10B 119.7 . . ?
C16A C11A C12A 118.74(12) . . ?
C16A C11A C3A 120.83(12) . . ?
C12A C11A C3A 120.41(12) . . ?
C13A C12A C11A 120.52(13) . . ?
C13A C12A H12B 119.7 . . ?
C11A C12A H12B 119.7 . . ?
C14A C13A C12A 120.19(14) . . ?
C14A C13A H13B 119.9 . . ?
C12A C13A H13B 119.9 . . ?
C13A C14A C15A 119.56(14) . . ?
C13A C14A H14B 120.2 . . ?
C15A C14A H14B 120.2 . . ?
C14A C15A C16A 120.50(14) . . ?
C14A C15A H15B 119.8 . . ?
C16A C15A H15B 119.8 . . ?
C15A C16A C11A 120.48(13) . . ?
C15A C16A H16B 119.8 . . ?
C11A C16A H16B 119.8 . . ?
N2A C17A C18A 111.91(12) . . ?
N2A C17A H17C 109.2 . . ?
C18A C17A H17C 109.2 . . ?
N2A C17A H17D 109.2 . . ?
C18A C17A H17D 109.2 . . ?
H17C C17A H17D 107.9 . . ?
C17A C18A H18D 109.5 . . ?
C17A C18A H18E 109.5 . . ?
H18D C18A H18E 109.5 . . ?
C17A C18A H18F 109.5 . . ?
H18D C18A H18F 109.5 . . ?
H18E C18A H18F 109.5 . . ?
N3A C19A C20A 112.03(12) . . ?
N3A C19A H19C 109.2 . . ?
C20A C19A H19C 109.2 . . ?
N3A C19A H19D 109.2 . . ?
C20A C19A H19D 109.2 . . ?
H19C C19A H19D 107.9 . . ?
C19A C20A H20D 109.5 . . ?
C19A C20A H20E 109.5 . . ?
H20D C20A H20E 109.5 . . ?
C19A C20A H20F 109.5 . . ?
H20D C20A H20F 109.5 . . ?
H20E C20A H20F 109.5 . . ?
C5S N1S C1S 116.30(17) . . ?
N1S C1S C2S 123.72(18) . . ?
N1S C1S H1SA 118.1 . . ?
C2S C1S H1SA 118.1 . . ?
C1S C2S C3S 118.77(18) . . ?
C1S C2S H2SA 120.6 . . ?
C3S C2S H2SA 120.6 . . ?
C2S C3S C4S 118.91(18) . . ?
C2S C3S H3SA 120.5 . . ?
C4S C3S H3SA 120.5 . . ?
C5S C4S C3S 118.27(17) . . ?
C5S C4S H4SA 120.9 . . ?
C3S C4S H4SA 120.9 . . ?
N1S C5S C4S 124.02(18) . . ?
N1S C5S H5SA 118.0 . . ?
C4S C5S H5SA 118.0 . . ?
C5SA N1SA C1SA 116.04(17) . . ?
N1SA C1SA C2SA 124.02(17) . . ?
N1SA C1SA H1SB 118.0 . . ?
C2SA C1SA H1SB 118.0 . . ?
C3SA C2SA C1SA 118.99(18) . . ?
C3SA C2SA H2SB 120.5 . . ?
C1SA C2SA H2SB 120.5 . . ?
C2SA C3SA C4SA 117.8(2) . . ?
C2SA C3SA H3SB 121.1 . . ?
C4SA C3SA H3SB 121.1 . . ?
C5SA C4SA C3SA 118.88(18) . . ?
C5SA C4SA H4SB 120.6 . . ?
C3SA C4SA H4SB 120.6 . . ?
N1SA C5SA C4SA 124.29(18) . . ?
N1SA C5SA H5SB 117.9 . . ?
C4SA C5SA H5SB 117.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C2 N1 C1 N4 -82.28(14) . . . . ?
C2 N1 C1 C5 146.75(11) . . . . ?
C2 N1 C1 C3 23.50(13) . . . . ?
C4 N4 C1 N1 126.41(12) . . . . ?
C4 N4 C1 C5 -102.57(13) . . . . ?
C4 N4 C1 C3 19.65(13) . . . . ?
C17 N2 C2 O1 2.9(2) . . . . ?
C3 N2 C2 O1 172.14(12) . . . . ?
C17 N2 C2 N1 -176.74(11) . . . . ?
C3 N2 C2 N1 -7.46(15) . . . . ?
C1 N1 C2 O1 168.76(13) . . . . ?
C1 N1 C2 N2 -11.65(15) . . . . ?
C4 N3 C3 N2 -80.55(13) . . . . ?
C19 N3 C3 N2 73.34(15) . . . . ?
C4 N3 C3 C11 148.94(11) . . . . ?
C19 N3 C3 C11 -57.17(16) . . . . ?
C4 N3 C3 C1 25.72(13) . . . . ?
C19 N3 C3 C1 179.62(11) . . . . ?
C2 N2 C3 N3 128.10(12) . . . . ?
C17 N2 C3 N3 -62.91(16) . . . . ?
C2 N2 C3 C11 -99.96(12) . . . . ?
C17 N2 C3 C11 69.03(15) . . . . ?
C2 N2 C3 C1 20.71(13) . . . . ?
C17 N2 C3 C1 -170.30(11) . . . . ?
N1 C1 C3 N3 -142.27(10) . . . . ?
N4 C1 C3 N3 -26.10(12) . . . . ?
C5 C1 C3 N3 95.26(12) . . . . ?
N1 C1 C3 N2 -25.19(12) . . . . ?
N4 C1 C3 N2 90.99(11) . . . . ?
C5 C1 C3 N2 -147.66(11) . . . . ?
N1 C1 C3 C11 93.94(12) . . . . ?
N4 C1 C3 C11 -149.88(11) . . . . ?
C5 C1 C3 C11 -28.52(15) . . . . ?
C1 N4 C4 O2 174.95(13) . . . . ?
C1 N4 C4 N3 -4.75(15) . . . . ?
C3 N3 C4 O2 165.55(13) . . . . ?
C19 N3 C4 O2 10.6(2) . . . . ?
C3 N3 C4 N4 -14.74(15) . . . . ?
C19 N3 C4 N4 -169.66(11) . . . . ?
N1 C1 C5 C6 -25.74(17) . . . . ?
N4 C1 C5 C6 -156.63(12) . . . . ?
C3 C1 C5 C6 89.85(15) . . . . ?
N1 C1 C5 C10 159.44(12) . . . . ?
N4 C1 C5 C10 28.55(17) . . . . ?
C3 C1 C5 C10 -84.97(15) . . . . ?
C10 C5 C6 C7 0.5(2) . . . . ?
C1 C5 C6 C7 -174.34(13) . . . . ?
C5 C6 C7 C8 1.1(2) . . . . ?
C6 C7 C8 C9 -1.4(2) . . . . ?
C7 C8 C9 C10 0.2(2) . . . . ?
C8 C9 C10 C5 1.4(2) . . . . ?
C6 C5 C10 C9 -1.8(2) . . . . ?
C1 C5 C10 C9 173.11(13) . . . . ?
N3 C3 C11 C16 -32.26(17) . . . . ?
N2 C3 C11 C16 -163.82(12) . . . . ?
C1 C3 C11 C16 84.10(15) . . . . ?
N3 C3 C11 C12 154.25(12) . . . . ?
N2 C3 C11 C12 22.69(17) . . . . ?
C1 C3 C11 C12 -89.39(15) . . . . ?
C16 C11 C12 C13 -0.9(2) . . . . ?
C3 C11 C12 C13 172.81(13) . . . . ?
C11 C12 C13 C14 0.4(2) . . . . ?
C12 C13 C14 C15 0.5(2) . . . . ?
C13 C14 C15 C16 -0.9(2) . . . . ?
C14 C15 C16 C11 0.4(2) . . . . ?
C12 C11 C16 C15 0.5(2) . . . . ?
C3 C11 C16 C15 -173.10(12) . . . . ?
C2 N2 C17 C18 -86.94(15) . . . . ?
C3 N2 C17 C18 105.20(14) . . . . ?
C4 N3 C19 C20 -73.61(16) . . . . ?
C3 N3 C19 C20 135.26(13) . . . . ?
C2A N1A C1A N4A -84.12(14) . . . . ?
C2A N1A C1A C5A 146.97(12) . . . . ?
C2A N1A C1A C3A 22.02(14) . . . . ?
C4A N4A C1A N1A 124.98(12) . . . . ?
C4A N4A C1A C5A -105.79(13) . . . . ?
C4A N4A C1A C3A 17.58(14) . . . . ?
C3A N2A C2A O1A 172.41(13) . . . . ?
C17A N2A C2A O1A 2.5(2) . . . . ?
C3A N2A C2A N1A -6.70(15) . . . . ?
C17A N2A C2A N1A -176.62(12) . . . . ?
C1A N1A C2A O1A 169.83(13) . . . . ?
C1A N1A C2A N2A -11.08(16) . . . . ?
C4A N3A C3A N2A -82.05(13) . . . . ?
C19A N3A C3A N2A 74.23(16) . . . . ?
C4A N3A C3A C11A 149.12(11) . . . . ?
C19A N3A C3A C11A -54.60(16) . . . . ?
C4A N3A C3A C1A 24.16(13) . . . . ?
C19A N3A C3A C1A -179.56(11) . . . . ?
C2A N2A C3A N3A 126.52(12) . . . . ?
C17A N2A C3A N3A -63.93(16) . . . . ?
C2A N2A C3A C11A -104.59(13) . . . . ?
C17A N2A C3A C11A 64.96(16) . . . . ?
C2A N2A C3A C1A 19.00(13) . . . . ?
C17A N2A C3A C1A -171.45(11) . . . . ?
N1A C1A C3A N3A -140.13(10) . . . . ?
N4A C1A C3A N3A -23.89(12) . . . . ?
C5A C1A C3A N3A 96.92(12) . . . . ?
N1A C1A C3A N2A -23.38(12) . . . . ?
N4A C1A C3A N2A 92.85(11) . . . . ?
C5A C1A C3A N2A -146.33(11) . . . . ?
N1A C1A C3A C11A 97.44(12) . . . . ?
N4A C1A C3A C11A -146.32(11) . . . . ?
C5A C1A C3A C11A -25.50(16) . . . . ?
C1A N4A C4A O2A 175.71(14) . . . . ?
C1A N4A C4A N3A -3.61(16) . . . . ?
C3A N3A C4A O2A 166.33(13) . . . . ?
C19A N3A C4A O2A 9.1(2) . . . . ?
C3A N3A C4A N4A -14.33(15) . . . . ?
C19A N3A C4A N4A -171.53(12) . . . . ?
N1A C1A C5A C10A 163.04(12) . . . . ?
N4A C1A C5A C10A 33.75(17) . . . . ?
C3A C1A C5A C10A -80.08(15) . . . . ?
N1A C1A C5A C6A -18.94(18) . . . . ?
N4A C1A C5A C6A -148.24(13) . . . . ?
C3A C1A C5A C6A 97.94(15) . . . . ?
C10A C5A C6A C7A -1.1(2) . . . . ?
C1A C5A C6A C7A -179.12(13) . . . . ?
C5A C6A C7A C8A 1.5(2) . . . . ?
C6A C7A C8A C9A -0.3(2) . . . . ?
C7A C8A C9A C10A -1.4(2) . . . . ?
C8A C9A C10A C5A 1.9(2) . . . . ?
C6A C5A C10A C9A -0.6(2) . . . . ?
C1A C5A C10A C9A 177.47(13) . . . . ?
N3A C3A C11A C16A -34.63(17) . . . . ?
N2A C3A C11A C16A -164.12(12) . . . . ?
C1A C3A C11A C16A 82.04(15) . . . . ?
N3A C3A C11A C12A 146.78(12) . . . . ?
N2A C3A C11A C12A 17.28(17) . . . . ?
C1A C3A C11A C12A -96.56(15) . . . . ?
C16A C11A C12A C13A 0.8(2) . . . . ?
C3A C11A C12A C13A 179.44(13) . . . . ?
C11A C12A C13A C14A -1.0(2) . . . . ?
C12A C13A C14A C15A 0.4(2) . . . . ?
C13A C14A C15A C16A 0.3(2) . . . . ?
C14A C15A C16A C11A -0.4(2) . . . . ?
C12A C11A C16A C15A -0.1(2) . . . . ?
C3A C11A C16A C15A -178.75(12) . . . . ?
C2A N2A C17A C18A -82.65(16) . . . . ?
C3A N2A C17A C18A 108.78(15) . . . . ?
C4A N3A C19A C20A -70.34(16) . . . . ?
C3A N3A C19A C20A 135.80(13) . . . . ?
C5S N1S C1S C2S -0.4(3) . . . . ?
N1S C1S C2S C3S 1.2(3) . . . . ?
C1S C2S C3S C4S -0.6(3) . . . . ?
C2S C3S C4S C5S -0.7(3) . . . . ?
C1S N1S C5S C4S -1.0(3) . . . . ?
C3S C4S C5S N1S 1.6(3) . . . . ?
C5SA N1SA C1SA C2SA -0.1(3) . . . . ?
N1SA C1SA C2SA C3SA 0.6(3) . . . . ?
C1SA C2SA C3SA C4SA -0.6(3) . . . . ?
C2SA C3SA C4SA C5SA 0.2(3) . . . . ?
C1SA N1SA C5SA C4SA -0.4(3) . . . . ?
C3SA C4SA C5SA N1SA 0.3(3) . . . . ?

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
N1 H1N O1 0.873(19) 1.95(2) 2.8194(15) 170.6(17) 2_755
N4 H4N O2A 0.898(19) 1.910(19) 2.7977(15) 169.2(17) 2_665
N1A H1NA O1A 0.89(2) 1.94(2) 2.8139(16) 168.8(18) 2_665
N4A H4NA O2 0.869(17) 2.035(18) 2.8813(15) 164.5(16) 2_665

_refine_diff_density_max         0.375
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.054



####################################################################### 
# 
# 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_1b-Me2CO
_database_code_depnum_ccdc_archive 'CCDC 2072850'
loop_
_audit_author_name
_audit_author_address
'Valentina Karnoukhova'
;A N Nesmeyanov Institute of Organoelement Compounds of Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2021-03-24 deposited with the CCDC.	2021-05-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H22 N4 O2, C3 H6 O'
_chemical_formula_sum            'C23 H28 N4 O3'
_chemical_formula_weight         408.49

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.0523(10)
_cell_length_b                   10.7345(13)
_cell_length_c                   13.0559(16)
_cell_angle_alpha                97.828(3)
_cell_angle_beta                 97.868(3)
_cell_angle_gamma                91.711(3)
_cell_volume                     1106.1(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    327
_cell_measurement_theta_min      3
_cell_measurement_theta_max      25

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.226
_exptl_crystal_F_000             436
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.083
_shelx_estimated_absorpt_T_min   0.978
_shelx_estimated_absorpt_T_max   0.985
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6666
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX DUO diffractometer'
_diffrn_detector_type            'Bruker APEX II CCD area detector'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14838
_diffrn_reflns_av_unetI/netI     0.0900
_diffrn_reflns_av_R_equivalents  0.0600
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.917
_diffrn_reflns_theta_max         29.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             6439
_reflns_number_gt                3845
_reflns_threshold_expression     I>2σ(I)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015b)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0478P)²+0.1146P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6439
_refine_ls_number_parameters     302
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1072
_refine_ls_R_factor_gt           0.0584
_refine_ls_wR_factor_ref         0.1403
_refine_ls_wR_factor_gt          0.1163
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_restrained_S_all      1.009
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.28685(15) 0.48580(11) 1.00614(10) 0.0253(3) Uani 1 1 d . . . . .
O2 O 0.27623(15) -0.04280(11) 0.96086(10) 0.0239(3) Uani 1 1 d . . . . .
N1 N 0.44043(19) 0.34792(14) 0.90946(12) 0.0196(3) Uani 1 1 d . . . . .
H1N H 0.536(3) 0.381(2) 0.9349(16) 0.035(6) Uiso 1 1 d . . . . .
N2 N 0.16811(17) 0.30935(13) 0.90045(11) 0.0176(3) Uani 1 1 d . . . . .
N3 N 0.17395(17) 0.08506(13) 0.84142(11) 0.0169(3) Uani 1 1 d . . . . .
N4 N 0.43046(19) 0.12733(14) 0.92736(11) 0.0189(3) Uani 1 1 d . . . . .
H4N H 0.523(3) 0.103(2) 0.9557(18) 0.043(7) Uiso 1 1 d . . . . .
C1 C 0.4148(2) 0.22097(15) 0.85680(13) 0.0170(3) Uani 1 1 d . . . . .
C2 C 0.2980(2) 0.38982(16) 0.94520(13) 0.0190(4) Uani 1 1 d . . . . .
C3 C 0.2172(2) 0.21123(15) 0.82322(13) 0.0160(3) Uani 1 1 d . . . . .
C4 C 0.2935(2) 0.04836(16) 0.91499(13) 0.0187(4) Uani 1 1 d . . . . .
C5 C 0.5163(2) 0.19328(16) 0.76795(13) 0.0189(4) Uani 1 1 d . . . . .
C6 C 0.5830(2) 0.28862(18) 0.72296(15) 0.0262(4) Uani 1 1 d . . . . .
H6A H 0.574356 0.373782 0.752211 0.031 Uiso 1 1 calc R U . . .
C7 C 0.6626(3) 0.2616(2) 0.63562(16) 0.0343(5) Uani 1 1 d . . . . .
H7A H 0.709410 0.328107 0.605804 0.041 Uiso 1 1 calc R U . . .
C8 C 0.6740(2) 0.1377(2) 0.59160(15) 0.0322(5) Uani 1 1 d . . . . .
H8A H 0.726352 0.119108 0.530746 0.039 Uiso 1 1 calc R U . . .
C9 C 0.6090(2) 0.04190(19) 0.63654(15) 0.0292(4) Uani 1 1 d . . . . .
H9A H 0.616658 -0.043216 0.606816 0.035 Uiso 1 1 calc R U . . .
C10 C 0.5328(2) 0.06949(17) 0.72488(14) 0.0240(4) Uani 1 1 d . . . . .
H10A H 0.490965 0.002789 0.756631 0.029 Uiso 1 1 calc R U . . .
C11 C 0.1614(2) 0.23646(16) 0.71298(13) 0.0182(3) Uani 1 1 d . . . . .
C12 C 0.1328(2) 0.35850(17) 0.69330(14) 0.0248(4) Uani 1 1 d . . . . .
H12A H 0.140545 0.425197 0.749862 0.030 Uiso 1 1 calc R U . . .
C13 C 0.0932(3) 0.38358(19) 0.59211(15) 0.0320(5) Uani 1 1 d . . . . .
H13A H 0.075817 0.467638 0.579507 0.038 Uiso 1 1 calc R U . . .
C14 C 0.0787(3) 0.28770(19) 0.50926(15) 0.0309(5) Uani 1 1 d . . . . .
H14A H 0.048655 0.305021 0.439860 0.037 Uiso 1 1 calc R U . . .
C15 C 0.1083(2) 0.16582(18) 0.52805(14) 0.0254(4) Uani 1 1 d . . . . .
H15A H 0.099968 0.099383 0.471251 0.030 Uiso 1 1 calc R U . . .
C16 C 0.1498(2) 0.14057(17) 0.62899(13) 0.0205(4) Uani 1 1 d . . . . .
H16A H 0.170626 0.056811 0.641151 0.025 Uiso 1 1 calc R U . . .
C17 C -0.0033(2) 0.33243(16) 0.91888(14) 0.0208(4) Uani 1 1 d . . . . .
H17A H -0.082570 0.286636 0.860240 0.025 Uiso 1 1 calc R U . . .
H17B H -0.022007 0.423477 0.921477 0.025 Uiso 1 1 calc R U . . .
C18 C -0.0380(3) 0.29018(18) 1.02004(16) 0.0304(5) Uani 1 1 d . . . . .
H18A H -0.154865 0.304863 1.029317 0.046 Uiso 1 1 calc R U . . .
H18B H 0.037065 0.338065 1.078512 0.046 Uiso 1 1 calc R U . . .
H18C H -0.018576 0.200228 1.017868 0.046 Uiso 1 1 calc R U . . .
C19 C 0.0029(2) 0.02901(16) 0.82347(14) 0.0223(4) Uani 1 1 d . . . . .
H19A H -0.071063 0.080908 0.781394 0.027 Uiso 1 1 calc R U . . .
H19B H -0.038754 0.029197 0.891410 0.027 Uiso 1 1 calc R U . . .
C20 C -0.0066(2) -0.10480(17) 0.76726(15) 0.0272(4) Uani 1 1 d . . . . .
H20A H -0.123454 -0.137878 0.754980 0.041 Uiso 1 1 calc R U . . .
H20B H 0.062045 -0.157469 0.810252 0.041 Uiso 1 1 calc R U . . .
H20C H 0.035488 -0.105537 0.700228 0.041 Uiso 1 1 calc R U . . .
O1S O 0.3376(18) 0.7673(14) 0.6559(7) 0.066(3) Uani 0.53(3) 1 d D . P A 1
C1S C 0.4306(12) 0.6991(13) 0.7005(17) 0.039(3) Uani 0.53(3) 1 d D . P A 1
O1S' O 0.2914(13) 0.694(3) 0.6463(6) 0.090(5) Uani 0.47(3) 1 d D . P A 2
C1S' C 0.4329(13) 0.679(2) 0.6861(19) 0.049(5) Uani 0.47(3) 1 d D . P A 2
C2S C 0.4569(4) 0.6941(3) 0.8092(2) 0.0682(9) Uani 1 1 d . . . . .
H2SA H 0.369241 0.739091 0.841927 0.102 Uiso 1 1 calc R U . A 1
H2SB H 0.567077 0.733714 0.839475 0.102 Uiso 1 1 calc R U . A 1
H2SC H 0.452463 0.606094 0.821423 0.102 Uiso 1 1 calc R U . A 1
C3S C 0.5548(4) 0.6287(3) 0.6345(2) 0.0710(9) Uani 1 1 d . . . . .
H3SA H 0.568168 0.672466 0.574767 0.107 Uiso 1 1 calc R U . A 1
H3SB H 0.510550 0.542321 0.609337 0.107 Uiso 1 1 calc R U . A 1
H3SC H 0.663914 0.627025 0.677857 0.107 Uiso 1 1 calc R U . A 1


_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 C2 1.226(2) . ?
O2 C4 1.229(2) . ?
N1 C2 1.362(2) . ?
N1 C1 1.436(2) . ?
N1 H1N 0.84(2) . ?
N2 C2 1.350(2) . ?
N2 C17 1.456(2) . ?
N2 C3 1.458(2) . ?
N3 C4 1.370(2) . ?
N3 C3 1.447(2) . ?
N3 C19 1.462(2) . ?
N4 C4 1.349(2) . ?
N4 C1 1.450(2) . ?
N4 H4N 0.85(2) . ?
C1 C5 1.510(2) . ?
C1 C3 1.589(2) . ?
C3 C11 1.511(2) . ?
C5 C6 1.378(2) . ?
C5 C10 1.388(2) . ?
C6 C7 1.384(3) . ?
C6 H6A 0.9500 . ?
C7 C8 1.386(3) . ?
C7 H7A 0.9500 . ?
C8 C9 1.376(3) . ?
C8 H8A 0.9500 . ?
C9 C10 1.381(3) . ?
C9 H9A 0.9500 . ?
C10 H10A 0.9500 . ?
C11 C16 1.389(2) . ?
C11 C12 1.389(2) . ?
C12 C13 1.381(3) . ?
C12 H12A 0.9500 . ?
C13 C14 1.378(3) . ?
C13 H13A 0.9500 . ?
C14 C15 1.385(3) . ?
C14 H14A 0.9500 . ?
C15 C16 1.380(2) . ?
C15 H15A 0.9500 . ?
C16 H16A 0.9500 . ?
C17 C18 1.511(2) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 C20 1.516(2) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
O1S C1S 1.211(3) . ?
C1S C2S 1.41(2) . ?
C1S C3S 1.55(2) . ?
O1S' C1S' 1.211(3) . ?
C1S' C3S 1.35(2) . ?
C1S' C2S 1.58(2) . ?
C2S H2SA 0.9800 . ?
C2S H2SB 0.9800 . ?
C2S H2SC 0.9800 . ?
C3S H3SA 0.9800 . ?
C3S H3SB 0.9800 . ?
C3S H3SC 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
C2 N1 C1 111.21(14) . . ?
C2 N1 H1N 122.0(15) . . ?
C1 N1 H1N 122.9(14) . . ?
C2 N2 C17 121.72(14) . . ?
C2 N2 C3 112.32(13) . . ?
C17 N2 C3 125.41(14) . . ?
C4 N3 C3 109.63(13) . . ?
C4 N3 C19 121.11(14) . . ?
C3 N3 C19 124.11(13) . . ?
C4 N4 C1 112.89(14) . . ?
C4 N4 H4N 118.4(16) . . ?
C1 N4 H4N 124.5(16) . . ?
N1 C1 N4 113.31(14) . . ?
N1 C1 C5 113.56(14) . . ?
N4 C1 C5 112.72(14) . . ?
N1 C1 C3 101.46(13) . . ?
N4 C1 C3 99.62(12) . . ?
C5 C1 C3 114.90(13) . . ?
O1 C2 N2 124.95(16) . . ?
O1 C2 N1 126.36(16) . . ?
N2 C2 N1 108.67(15) . . ?
N3 C3 N2 113.51(13) . . ?
N3 C3 C11 114.19(14) . . ?
N2 C3 C11 111.78(13) . . ?
N3 C3 C1 102.04(12) . . ?
N2 C3 C1 99.91(12) . . ?
C11 C3 C1 114.20(13) . . ?
O2 C4 N4 126.49(16) . . ?
O2 C4 N3 124.46(16) . . ?
N4 C4 N3 109.04(15) . . ?
C6 C5 C10 118.64(17) . . ?
C6 C5 C1 121.42(16) . . ?
C10 C5 C1 119.76(16) . . ?
C5 C6 C7 120.71(18) . . ?
C5 C6 H6A 119.6 . . ?
C7 C6 H6A 119.6 . . ?
C6 C7 C8 120.06(19) . . ?
C6 C7 H7A 120.0 . . ?
C8 C7 H7A 120.0 . . ?
C9 C8 C7 119.62(18) . . ?
C9 C8 H8A 120.2 . . ?
C7 C8 H8A 120.2 . . ?
C8 C9 C10 119.97(18) . . ?
C8 C9 H9A 120.0 . . ?
C10 C9 H9A 120.0 . . ?
C9 C10 C5 120.96(18) . . ?
C9 C10 H10A 119.5 . . ?
C5 C10 H10A 119.5 . . ?
C16 C11 C12 118.71(16) . . ?
C16 C11 C3 121.01(15) . . ?
C12 C11 C3 120.11(15) . . ?
C13 C12 C11 120.47(17) . . ?
C13 C12 H12A 119.8 . . ?
C11 C12 H12A 119.8 . . ?
C14 C13 C12 120.54(18) . . ?
C14 C13 H13A 119.7 . . ?
C12 C13 H13A 119.7 . . ?
C13 C14 C15 119.40(18) . . ?
C13 C14 H14A 120.3 . . ?
C15 C14 H14A 120.3 . . ?
C16 C15 C14 120.23(18) . . ?
C16 C15 H15A 119.9 . . ?
C14 C15 H15A 119.9 . . ?
C15 C16 C11 120.64(17) . . ?
C15 C16 H16A 119.7 . . ?
C11 C16 H16A 119.7 . . ?
N2 C17 C18 111.40(15) . . ?
N2 C17 H17A 109.3 . . ?
C18 C17 H17A 109.3 . . ?
N2 C17 H17B 109.3 . . ?
C18 C17 H17B 109.3 . . ?
H17A C17 H17B 108.0 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N3 C19 C20 112.10(15) . . ?
N3 C19 H19A 109.2 . . ?
C20 C19 H19A 109.2 . . ?
N3 C19 H19B 109.2 . . ?
C20 C19 H19B 109.2 . . ?
H19A C19 H19B 107.9 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O1S C1S C2S 126.3(17) . . ?
O1S C1S C3S 115.9(15) . . ?
C2S C1S C3S 116.9(5) . . ?
O1S' C1S' C3S 125(2) . . ?
O1S' C1S' C2S 114.2(18) . . ?
C3S C1S' C2S 119.5(6) . . ?
C1S C2S H2SA 109.5 . . ?
C1S C2S H2SB 109.5 . . ?
H2SA C2S H2SB 109.5 . . ?
C1S C2S H2SC 109.5 . . ?
H2SA C2S H2SC 109.5 . . ?
H2SB C2S H2SC 109.5 . . ?
C1S C3S H3SA 109.5 . . ?
C1S C3S H3SB 109.5 . . ?
H3SA C3S H3SB 109.5 . . ?
C1S C3S H3SC 109.5 . . ?
H3SA C3S H3SC 109.5 . . ?
H3SB C3S H3SC 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
C2 N1 C1 N4 -82.38(18) . . . . ?
C2 N1 C1 C5 147.31(15) . . . . ?
C2 N1 C1 C3 23.46(17) . . . . ?
C4 N4 C1 N1 124.48(16) . . . . ?
C4 N4 C1 C5 -104.79(17) . . . . ?
C4 N4 C1 C3 17.48(17) . . . . ?
C17 N2 C2 O1 2.0(3) . . . . ?
C3 N2 C2 O1 173.88(16) . . . . ?
C17 N2 C2 N1 -176.65(15) . . . . ?
C3 N2 C2 N1 -4.74(19) . . . . ?
C1 N1 C2 O1 168.18(17) . . . . ?
C1 N1 C2 N2 -13.2(2) . . . . ?
C4 N3 C3 N2 -81.96(17) . . . . ?
C19 N3 C3 N2 72.7(2) . . . . ?
C4 N3 C3 C11 148.31(14) . . . . ?
C19 N3 C3 C11 -57.0(2) . . . . ?
C4 N3 C3 C1 24.58(17) . . . . ?
C19 N3 C3 C1 179.26(14) . . . . ?
C2 N2 C3 N3 126.00(15) . . . . ?
C17 N2 C3 N3 -62.4(2) . . . . ?
C2 N2 C3 C11 -103.07(16) . . . . ?
C17 N2 C3 C11 68.5(2) . . . . ?
C2 N2 C3 C1 18.13(17) . . . . ?
C17 N2 C3 C1 -170.32(15) . . . . ?
N1 C1 C3 N3 -140.50(13) . . . . ?
N4 C1 C3 N3 -24.14(15) . . . . ?
C5 C1 C3 N3 96.56(15) . . . . ?
N1 C1 C3 N2 -23.67(15) . . . . ?
N4 C1 C3 N2 92.69(13) . . . . ?
C5 C1 C3 N2 -146.61(14) . . . . ?
N1 C1 C3 C11 95.78(16) . . . . ?
N4 C1 C3 C11 -147.87(14) . . . . ?
C5 C1 C3 C11 -27.17(19) . . . . ?
C1 N4 C4 O2 176.36(17) . . . . ?
C1 N4 C4 N3 -3.21(19) . . . . ?
C3 N3 C4 O2 165.60(16) . . . . ?
C19 N3 C4 O2 10.0(3) . . . . ?
C3 N3 C4 N4 -14.82(19) . . . . ?
C19 N3 C4 N4 -170.39(15) . . . . ?
N1 C1 C5 C6 -18.8(2) . . . . ?
N4 C1 C5 C6 -149.42(16) . . . . ?
C3 C1 C5 C6 97.37(19) . . . . ?
N1 C1 C5 C10 166.12(15) . . . . ?
N4 C1 C5 C10 35.5(2) . . . . ?
C3 C1 C5 C10 -77.68(19) . . . . ?
C10 C5 C6 C7 1.0(3) . . . . ?
C1 C5 C6 C7 -174.10(17) . . . . ?
C5 C6 C7 C8 0.8(3) . . . . ?
C6 C7 C8 C9 -1.4(3) . . . . ?
C7 C8 C9 C10 0.1(3) . . . . ?
C8 C9 C10 C5 1.7(3) . . . . ?
C6 C5 C10 C9 -2.3(3) . . . . ?
C1 C5 C10 C9 172.90(16) . . . . ?
N3 C3 C11 C16 -30.2(2) . . . . ?
N2 C3 C11 C16 -160.81(15) . . . . ?
C1 C3 C11 C16 86.68(19) . . . . ?
N3 C3 C11 C12 154.58(15) . . . . ?
N2 C3 C11 C12 24.0(2) . . . . ?
C1 C3 C11 C12 -88.51(19) . . . . ?
C16 C11 C12 C13 0.2(3) . . . . ?
C3 C11 C12 C13 175.47(17) . . . . ?
C11 C12 C13 C14 1.1(3) . . . . ?
C12 C13 C14 C15 -1.6(3) . . . . ?
C13 C14 C15 C16 0.8(3) . . . . ?
C14 C15 C16 C11 0.4(3) . . . . ?
C12 C11 C16 C15 -0.9(3) . . . . ?
C3 C11 C16 C15 -176.18(16) . . . . ?
C2 N2 C17 C18 -82.4(2) . . . . ?
C3 N2 C17 C18 106.83(18) . . . . ?
C4 N3 C19 C20 -72.8(2) . . . . ?
C3 N3 C19 C20 135.26(16) . . . . ?

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
N1 H1N O1 0.84(2) 1.99(2) 2.7912(19) 159(2) 2_667
N4 H4N O2 0.85(2) 2.00(2) 2.8419(19) 172(2) 2_657

_refine_diff_density_max         0.331
_refine_diff_density_min         -0.253
_refine_diff_density_rms         0.054



####################################################################### 
# 
# 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_1a-cyclohexanone
_database_code_depnum_ccdc_archive 'CCDC 2072846'
loop_
_audit_author_name
_audit_author_address
'Valentina Karnoukhova'
;A N Nesmeyanov Institute of Organoelement Compounds of Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2021-03-24 deposited with the CCDC.	2021-05-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H18 N4 O2, C6 H10 O'
_chemical_formula_sum            'C24 H28 N4 O3'
_chemical_formula_weight         420.50

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   10.5144(6)
_cell_length_b                   13.2689(7)
_cell_length_c                   15.6124(8)
_cell_angle_alpha                90
_cell_angle_beta                 91.5967(12)
_cell_angle_gamma                90
_cell_volume                     2177.3(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    241
_cell_measurement_theta_min      3
_cell_measurement_theta_max      25

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.283
_exptl_crystal_F_000             896
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.160
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    0.086
_shelx_estimated_absorpt_T_min   0.977
_shelx_estimated_absorpt_T_max   0.989
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6789
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX DUO diffractometer'
_diffrn_detector_type            'Bruker APEX II CCD area detector'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            28543
_diffrn_reflns_av_unetI/netI     0.0451
_diffrn_reflns_av_R_equivalents  0.0558
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.938
_diffrn_reflns_theta_max         29.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             6342
_reflns_number_gt                4582
_reflns_threshold_expression     I>2σ(I)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015b)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0470P)²+0.9674P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6342
_refine_ls_number_parameters     290
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0754
_refine_ls_R_factor_gt           0.0473
_refine_ls_wR_factor_ref         0.1177
_refine_ls_wR_factor_gt          0.1031
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_restrained_S_all      1.009
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 -0.02095(9) 0.36741(7) 1.02504(6) 0.0182(2) Uani 1 1 d . . . . .
O2 O 0.53204(9) 0.36651(7) 1.02272(7) 0.0193(2) Uani 1 1 d . . . . .
N1 N 0.14883(11) 0.44265(9) 0.95902(7) 0.0147(2) Uani 1 1 d . . . . .
H1N H 0.1160(17) 0.5037(15) 0.9595(12) 0.027(5) Uiso 1 1 d . . . . .
N2 N 0.12843(10) 0.27579(8) 0.95292(7) 0.0141(2) Uani 1 1 d . . . . .
N3 N 0.36043(11) 0.27727(8) 0.96904(7) 0.0142(2) Uani 1 1 d . . . . .
N4 N 0.37562(11) 0.43939(9) 0.93555(8) 0.0154(2) Uani 1 1 d . . . . .
H4N H 0.3972(17) 0.5037(15) 0.9477(12) 0.028(5) Uiso 1 1 d . . . . .
C1 C 0.25007(12) 0.41380(10) 0.90223(8) 0.0122(2) Uani 1 1 d . . . . .
C2 C 0.07628(12) 0.36320(10) 0.98310(8) 0.0138(2) Uani 1 1 d . . . . .
C3 C 0.24893(12) 0.29327(10) 0.91220(8) 0.0119(2) Uani 1 1 d . . . . .
C4 C 0.43143(12) 0.36196(10) 0.98015(8) 0.0146(3) Uani 1 1 d . . . . .
C5 C 0.22594(12) 0.45295(10) 0.81162(8) 0.0135(2) Uani 1 1 d . . . . .
C6 C 0.10224(13) 0.45584(10) 0.77709(9) 0.0179(3) Uani 1 1 d . . . . .
H6A H 0.033097 0.435751 0.811070 0.021 Uiso 1 1 calc R U . . .
C7 C 0.07936(15) 0.48792(11) 0.69325(10) 0.0235(3) Uani 1 1 d . . . . .
H7A H -0.005271 0.489651 0.670339 0.028 Uiso 1 1 calc R U . . .
C8 C 0.17955(16) 0.51741(11) 0.64289(9) 0.0244(3) Uani 1 1 d . . . . .
H8A H 0.163882 0.539140 0.585581 0.029 Uiso 1 1 calc R U . . .
C9 C 0.30268(16) 0.51487(11) 0.67699(10) 0.0242(3) Uani 1 1 d . . . . .
H9A H 0.371618 0.535104 0.642887 0.029 Uiso 1 1 calc R U . . .
C10 C 0.32602(14) 0.48278(11) 0.76107(9) 0.0187(3) Uani 1 1 d . . . . .
H10A H 0.410704 0.481308 0.783892 0.022 Uiso 1 1 calc R U . . .
C11 C 0.26038(12) 0.23592(10) 0.82868(8) 0.0131(2) Uani 1 1 d . . . . .
C12 C 0.15324(13) 0.19947(10) 0.78462(9) 0.0168(3) Uani 1 1 d . . . . .
H12A H 0.071741 0.206818 0.808652 0.020 Uiso 1 1 calc R U . . .
C13 C 0.16453(14) 0.15221(11) 0.70542(9) 0.0202(3) Uani 1 1 d . . . . .
H13A H 0.090878 0.127581 0.675647 0.024 Uiso 1 1 calc R U . . .
C14 C 0.28314(15) 0.14119(11) 0.67017(9) 0.0205(3) Uani 1 1 d . . . . .
H14A H 0.290965 0.108378 0.616494 0.025 Uiso 1 1 calc R U . . .
C15 C 0.39062(14) 0.17809(11) 0.71327(9) 0.0201(3) Uani 1 1 d . . . . .
H15A H 0.471865 0.171170 0.688788 0.024 Uiso 1 1 calc R U . . .
C16 C 0.37939(13) 0.22512(10) 0.79216(9) 0.0167(3) Uani 1 1 d . . . . .
H16A H 0.453195 0.250139 0.821506 0.020 Uiso 1 1 calc R U . . .
C17 C 0.09178(15) 0.17877(11) 0.98837(10) 0.0228(3) Uani 1 1 d . . . . .
H17A H -0.001144 0.172725 0.986232 0.034 Uiso 1 1 calc R U . . .
H17B H 0.122915 0.173965 1.047982 0.034 Uiso 1 1 calc R U . . .
H17C H 0.128932 0.124392 0.954738 0.034 Uiso 1 1 calc R U . . .
C18 C 0.40441(15) 0.17899(11) 0.99909(10) 0.0222(3) Uani 1 1 d . . . . .
H18A H 0.497525 0.176601 0.998350 0.033 Uiso 1 1 calc R U . . .
H18B H 0.368954 0.126314 0.961459 0.033 Uiso 1 1 calc R U . . .
H18C H 0.376317 0.167937 1.057675 0.033 Uiso 1 1 calc R U . . .
O1S O 0.75218(14) 0.05300(10) 0.06537(9) 0.0441(3) Uani 1 1 d . . . . .
C1S C 0.72340(14) 0.11297(12) 0.12036(10) 0.0232(3) Uani 1 1 d . . . . .
C2S C 0.76274(15) 0.22170(12) 0.11903(10) 0.0249(3) Uani 1 1 d . . . . .
H2SA H 0.686638 0.264781 0.110131 0.030 Uiso 1 1 calc R U . . .
H2SB H 0.820184 0.233370 0.070846 0.030 Uiso 1 1 calc R U . . .
C3S C 0.83092(15) 0.25031(12) 0.20351(11) 0.0267(3) Uani 1 1 d . . . . .
H3SA H 0.913211 0.214201 0.208161 0.032 Uiso 1 1 calc R U . . .
H3SB H 0.848923 0.323547 0.203669 0.032 Uiso 1 1 calc R U . . .
C4S C 0.75128(16) 0.22420(12) 0.28055(11) 0.0286(3) Uani 1 1 d . . . . .
H4SA H 0.800266 0.240113 0.333917 0.034 Uiso 1 1 calc R U . . .
H4SB H 0.673192 0.265927 0.279332 0.034 Uiso 1 1 calc R U . . .
C5S C 0.71465(17) 0.11327(12) 0.28064(11) 0.0279(3) Uani 1 1 d . . . . .
H5SA H 0.657820 0.100058 0.328883 0.033 Uiso 1 1 calc R U . . .
H5SB H 0.792199 0.071812 0.289457 0.033 Uiso 1 1 calc R U . . .
C6S C 0.64702(15) 0.08226(12) 0.19626(10) 0.0245(3) Uani 1 1 d . . . . .
H6SA H 0.634565 0.008310 0.195574 0.029 Uiso 1 1 calc R U . . .
H6SB H 0.562178 0.114554 0.192281 0.029 Uiso 1 1 calc R U . . .


_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 C2 1.2306(16) . ?
O2 C4 1.2350(16) . ?
N1 C2 1.3603(17) . ?
N1 C1 1.4555(17) . ?
N1 H1N 0.880(19) . ?
N2 C2 1.3720(17) . ?
N2 C3 1.4519(16) . ?
N2 C17 1.4574(18) . ?
N3 C4 1.3576(17) . ?
N3 C18 1.4568(17) . ?
N3 C3 1.4659(16) . ?
N4 C4 1.3645(17) . ?
N4 C1 1.4457(17) . ?
N4 H4N 0.902(19) . ?
C1 C5 1.5217(18) . ?
C1 C3 1.6069(18) . ?
C3 C11 1.5175(18) . ?
C5 C10 1.3903(19) . ?
C5 C6 1.3945(19) . ?
C6 C7 1.391(2) . ?
C6 H6A 0.9500 . ?
C7 C8 1.388(2) . ?
C7 H7A 0.9500 . ?
C8 C9 1.387(2) . ?
C8 H8A 0.9500 . ?
C9 C10 1.395(2) . ?
C9 H9A 0.9500 . ?
C10 H10A 0.9500 . ?
C11 C12 1.3902(18) . ?
C11 C16 1.3969(18) . ?
C12 C13 1.395(2) . ?
C12 H12A 0.9500 . ?
C13 C14 1.385(2) . ?
C13 H13A 0.9500 . ?
C14 C15 1.388(2) . ?
C14 H14A 0.9500 . ?
C15 C16 1.389(2) . ?
C15 H15A 0.9500 . ?
C16 H16A 0.9500 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
O1S C1S 1.215(2) . ?
C1S C2S 1.501(2) . ?
C1S C6S 1.506(2) . ?
C2S C3S 1.531(2) . ?
C2S H2SA 0.9900 . ?
C2S H2SB 0.9900 . ?
C3S C4S 1.524(2) . ?
C3S H3SA 0.9900 . ?
C3S H3SB 0.9900 . ?
C4S C5S 1.522(2) . ?
C4S H4SA 0.9900 . ?
C4S H4SB 0.9900 . ?
C5S C6S 1.536(2) . ?
C5S H5SA 0.9900 . ?
C5S H5SB 0.9900 . ?
C6S H6SA 0.9900 . ?
C6S H6SB 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 N1 C1 112.94(11) . . ?
C2 N1 H1N 119.1(12) . . ?
C1 N1 H1N 122.8(12) . . ?
C2 N2 C3 112.17(11) . . ?
C2 N2 C17 120.25(11) . . ?
C3 N2 C17 123.41(11) . . ?
C4 N3 C18 122.10(11) . . ?
C4 N3 C3 112.65(11) . . ?
C18 N3 C3 124.46(11) . . ?
C4 N4 C1 112.46(11) . . ?
C4 N4 H4N 120.2(12) . . ?
C1 N4 H4N 121.3(12) . . ?
N4 C1 N1 113.26(11) . . ?
N4 C1 C5 112.41(11) . . ?
N1 C1 C5 111.76(10) . . ?
N4 C1 C3 102.01(10) . . ?
N1 C1 C3 101.26(10) . . ?
C5 C1 C3 115.36(10) . . ?
O1 C2 N1 126.33(12) . . ?
O1 C2 N2 124.54(12) . . ?
N1 C2 N2 109.12(11) . . ?
N2 C3 N3 113.88(10) . . ?
N2 C3 C11 112.78(10) . . ?
N3 C3 C11 111.49(10) . . ?
N2 C3 C1 102.14(10) . . ?
N3 C3 C1 101.23(10) . . ?
C11 C3 C1 114.51(10) . . ?
O2 C4 N3 124.68(12) . . ?
O2 C4 N4 125.98(12) . . ?
N3 C4 N4 109.33(11) . . ?
C10 C5 C6 119.03(12) . . ?
C10 C5 C1 121.04(12) . . ?
C6 C5 C1 119.89(12) . . ?
C7 C6 C5 120.48(13) . . ?
C7 C6 H6A 119.8 . . ?
C5 C6 H6A 119.8 . . ?
C8 C7 C6 120.34(14) . . ?
C8 C7 H7A 119.8 . . ?
C6 C7 H7A 119.8 . . ?
C9 C8 C7 119.39(13) . . ?
C9 C8 H8A 120.3 . . ?
C7 C8 H8A 120.3 . . ?
C8 C9 C10 120.44(14) . . ?
C8 C9 H9A 119.8 . . ?
C10 C9 H9A 119.8 . . ?
C5 C10 C9 120.32(13) . . ?
C5 C10 H10A 119.8 . . ?
C9 C10 H10A 119.8 . . ?
C12 C11 C16 119.02(12) . . ?
C12 C11 C3 121.13(12) . . ?
C16 C11 C3 119.70(11) . . ?
C11 C12 C13 120.49(13) . . ?
C11 C12 H12A 119.8 . . ?
C13 C12 H12A 119.8 . . ?
C14 C13 C12 119.98(13) . . ?
C14 C13 H13A 120.0 . . ?
C12 C13 H13A 120.0 . . ?
C13 C14 C15 120.01(13) . . ?
C13 C14 H14A 120.0 . . ?
C15 C14 H14A 120.0 . . ?
C14 C15 C16 120.02(13) . . ?
C14 C15 H15A 120.0 . . ?
C16 C15 H15A 120.0 . . ?
C15 C16 C11 120.49(13) . . ?
C15 C16 H16A 119.8 . . ?
C11 C16 H16A 119.8 . . ?
N2 C17 H17A 109.5 . . ?
N2 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
N2 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
N3 C18 H18A 109.5 . . ?
N3 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
N3 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O1S C1S C2S 123.06(15) . . ?
O1S C1S C6S 121.85(15) . . ?
C2S C1S C6S 115.09(13) . . ?
C1S C2S C3S 110.42(13) . . ?
C1S C2S H2SA 109.6 . . ?
C3S C2S H2SA 109.6 . . ?
C1S C2S H2SB 109.6 . . ?
C3S C2S H2SB 109.6 . . ?
H2SA C2S H2SB 108.1 . . ?
C4S C3S C2S 111.65(13) . . ?
C4S C3S H3SA 109.3 . . ?
C2S C3S H3SA 109.3 . . ?
C4S C3S H3SB 109.3 . . ?
C2S C3S H3SB 109.3 . . ?
H3SA C3S H3SB 108.0 . . ?
C5S C4S C3S 111.42(13) . . ?
C5S C4S H4SA 109.3 . . ?
C3S C4S H4SA 109.3 . . ?
C5S C4S H4SB 109.3 . . ?
C3S C4S H4SB 109.3 . . ?
H4SA C4S H4SB 108.0 . . ?
C4S C5S C6S 111.69(13) . . ?
C4S C5S H5SA 109.3 . . ?
C6S C5S H5SA 109.3 . . ?
C4S C5S H5SB 109.3 . . ?
C6S C5S H5SB 109.3 . . ?
H5SA C5S H5SB 107.9 . . ?
C1S C6S C5S 110.99(13) . . ?
C1S C6S H6SA 109.4 . . ?
C5S C6S H6SA 109.4 . . ?
C1S C6S H6SB 109.4 . . ?
C5S C6S H6SB 109.4 . . ?
H6SA C6S H6SB 108.0 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C4 N4 C1 N1 93.22(13) . . . . ?
C4 N4 C1 C5 -138.92(12) . . . . ?
C4 N4 C1 C3 -14.76(14) . . . . ?
C2 N1 C1 N4 -121.50(12) . . . . ?
C2 N1 C1 C5 110.30(12) . . . . ?
C2 N1 C1 C3 -13.05(13) . . . . ?
C1 N1 C2 O1 -173.90(12) . . . . ?
C1 N1 C2 N2 5.96(15) . . . . ?
C3 N2 C2 O1 -174.90(12) . . . . ?
C17 N2 C2 O1 -17.1(2) . . . . ?
C3 N2 C2 N1 5.23(15) . . . . ?
C17 N2 C2 N1 163.04(12) . . . . ?
C2 N2 C3 N3 95.58(13) . . . . ?
C17 N2 C3 N3 -61.42(16) . . . . ?
C2 N2 C3 C11 -136.08(11) . . . . ?
C17 N2 C3 C11 66.93(16) . . . . ?
C2 N2 C3 C1 -12.66(13) . . . . ?
C17 N2 C3 C1 -169.66(12) . . . . ?
C4 N3 C3 N2 -118.59(12) . . . . ?
C18 N3 C3 N2 71.44(16) . . . . ?
C4 N3 C3 C11 112.41(12) . . . . ?
C18 N3 C3 C11 -57.57(16) . . . . ?
C4 N3 C3 C1 -9.78(13) . . . . ?
C18 N3 C3 C1 -179.76(12) . . . . ?
N4 C1 C3 N2 131.64(10) . . . . ?
N1 C1 C3 N2 14.63(12) . . . . ?
C5 C1 C3 N2 -106.21(12) . . . . ?
N4 C1 C3 N3 13.94(12) . . . . ?
N1 C1 C3 N3 -103.07(10) . . . . ?
C5 C1 C3 N3 136.10(11) . . . . ?
N4 C1 C3 C11 -106.13(12) . . . . ?
N1 C1 C3 C11 136.87(11) . . . . ?
C5 C1 C3 C11 16.03(15) . . . . ?
C18 N3 C4 O2 -7.1(2) . . . . ?
C3 N3 C4 O2 -177.38(12) . . . . ?
C18 N3 C4 N4 171.47(12) . . . . ?
C3 N3 C4 N4 1.22(15) . . . . ?
C1 N4 C4 O2 -171.95(13) . . . . ?
C1 N4 C4 N3 9.47(16) . . . . ?
N4 C1 C5 C10 17.08(17) . . . . ?
N1 C1 C5 C10 145.74(12) . . . . ?
C3 C1 C5 C10 -99.31(14) . . . . ?
N4 C1 C5 C6 -165.24(12) . . . . ?
N1 C1 C5 C6 -36.58(16) . . . . ?
C3 C1 C5 C6 78.36(15) . . . . ?
C10 C5 C6 C7 0.1(2) . . . . ?
C1 C5 C6 C7 -177.60(13) . . . . ?
C5 C6 C7 C8 0.0(2) . . . . ?
C6 C7 C8 C9 -0.2(2) . . . . ?
C7 C8 C9 C10 0.1(2) . . . . ?
C6 C5 C10 C9 -0.2(2) . . . . ?
C1 C5 C10 C9 177.55(13) . . . . ?
C8 C9 C10 C5 0.0(2) . . . . ?
N2 C3 C11 C12 19.47(17) . . . . ?
N3 C3 C11 C12 149.05(12) . . . . ?
C1 C3 C11 C12 -96.78(14) . . . . ?
N2 C3 C11 C16 -164.86(12) . . . . ?
N3 C3 C11 C16 -35.29(16) . . . . ?
C1 C3 C11 C16 78.89(15) . . . . ?
C16 C11 C12 C13 0.4(2) . . . . ?
C3 C11 C12 C13 176.14(12) . . . . ?
C11 C12 C13 C14 0.1(2) . . . . ?
C12 C13 C14 C15 -0.7(2) . . . . ?
C13 C14 C15 C16 0.7(2) . . . . ?
C14 C15 C16 C11 -0.1(2) . . . . ?
C12 C11 C16 C15 -0.4(2) . . . . ?
C3 C11 C16 C15 -176.18(13) . . . . ?
O1S C1S C2S C3S -125.92(17) . . . . ?
C6S C1S C2S C3S 52.94(18) . . . . ?
C1S C2S C3S C4S -53.70(17) . . . . ?
C2S C3S C4S C5S 55.81(18) . . . . ?
C3S C4S C5S C6S -54.73(19) . . . . ?
O1S C1S C6S C5S 126.71(17) . . . . ?
C2S C1S C6S C5S -52.16(18) . . . . ?
C4S C5S C6S C1S 51.90(19) . . . . ?

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
N1 H1N O1 0.880(19) 1.999(19) 2.8706(15) 170.3(17) 3_567
N4 H4N O2 0.902(19) 1.927(19) 2.8223(15) 171.6(17) 3_667

_refine_diff_density_max         0.399
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.051



####################################################################### 
# 
# 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_1b-EtOH
_database_code_depnum_ccdc_archive 'CCDC 2072848'
loop_
_audit_author_name
_audit_author_address
'Valentina Karnoukhova'
;A N Nesmeyanov Institute of Organoelement Compounds of Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2021-03-24 deposited with the CCDC.	2021-05-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H22 N4 O2, C2 H6 O'
_chemical_formula_sum            'C22 H28 N4 O3'
_chemical_formula_weight         396.48

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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   12.5231(9)
_cell_length_b                   12.9844(10)
_cell_length_c                   13.4742(10)
_cell_angle_alpha                103.8760(16)
_cell_angle_beta                 96.9424(17)
_cell_angle_gamma                97.1860(17)
_cell_volume                     2084.3(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    543
_cell_measurement_theta_min      3
_cell_measurement_theta_max      25

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.264
_exptl_crystal_F_000             848
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.290
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.086
_shelx_estimated_absorpt_T_min   0.976
_shelx_estimated_absorpt_T_max   0.983
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6833
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX DUO diffractometer'
_diffrn_detector_type            'Bruker APEX II CCD area detector'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            37248
_diffrn_reflns_av_unetI/netI     0.0625
_diffrn_reflns_av_R_equivalents  0.0558
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         1.576
_diffrn_reflns_theta_max         29.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             12149
_reflns_number_gt                8319
_reflns_threshold_expression     I>2σ(I)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015b)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0617P)²+1.0227P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         12149
_refine_ls_number_parameters     578
_refine_ls_number_restraints     24
_refine_ls_R_factor_all          0.0905
_refine_ls_R_factor_gt           0.0572
_refine_ls_wR_factor_ref         0.1510
_refine_ls_wR_factor_gt          0.1335
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_restrained_S_all      1.016
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 1.01704(10) 1.09826(9) 0.12129(9) 0.0190(3) Uani 1 1 d . . . . .
O2 O 0.93515(10) 0.80524(10) 0.36274(9) 0.0226(3) Uani 1 1 d . . . . .
N1 N 0.90708(12) 0.93215(11) 0.07560(11) 0.0162(3) Uani 1 1 d . . . . .
H1N H 0.9305(18) 0.9039(17) 0.0203(18) 0.025(6) Uiso 1 1 d . . . . .
N2 N 0.89515(11) 1.04728(11) 0.22183(10) 0.0152(3) Uani 1 1 d . . . . .
N3 N 0.82222(11) 0.91234(11) 0.30474(10) 0.0155(3) Uani 1 1 d . . . . .
N4 N 0.91543(11) 0.81929(12) 0.19423(11) 0.0157(3) Uani 1 1 d . . . . .
H4N H 0.9396(18) 0.7597(19) 0.1707(17) 0.030(6) Uiso 1 1 d . . . . .
C1 C 0.84598(13) 0.86684(13) 0.12882(12) 0.0142(3) Uani 1 1 d . . . . .
C2 C 0.94627(13) 1.03132(13) 0.13788(12) 0.0152(3) Uani 1 1 d . . . . .
C3 C 0.80999(13) 0.95648(13) 0.21579(12) 0.0141(3) Uani 1 1 d . . . . .
C4 C 0.89482(13) 0.84179(13) 0.29329(13) 0.0168(3) Uani 1 1 d . . . . .
C5 C 0.75584(13) 0.78508(13) 0.05668(12) 0.0149(3) Uani 1 1 d . . . . .
C6 C 0.70508(14) 0.80767(14) -0.03165(13) 0.0184(3) Uani 1 1 d . . . . .
H6A H 0.727570 0.874164 -0.046671 0.022 Uiso 1 1 calc R U . . .
C7 C 0.62177(14) 0.73342(15) -0.09781(14) 0.0210(4) Uani 1 1 d . . . . .
H7A H 0.587694 0.749143 -0.158162 0.025 Uiso 1 1 calc R U . . .
C8 C 0.58802(14) 0.63644(15) -0.07631(14) 0.0228(4) Uani 1 1 d . . . . .
H8A H 0.531073 0.585621 -0.121820 0.027 Uiso 1 1 calc R U . . .
C9 C 0.63761(15) 0.61408(15) 0.01162(14) 0.0227(4) Uani 1 1 d . . . . .
H9A H 0.614219 0.547919 0.026878 0.027 Uiso 1 1 calc R U . . .
C10 C 0.72154(14) 0.68780(14) 0.07790(13) 0.0184(3) Uani 1 1 d . . . . .
H10A H 0.755615 0.671610 0.137997 0.022 Uiso 1 1 calc R U . . .
C11 C 0.69712(13) 0.98261(13) 0.19126(12) 0.0155(3) Uani 1 1 d . . . . .
C12 C 0.68144(14) 1.06855(14) 0.14939(13) 0.0200(3) Uani 1 1 d . . . . .
H12A H 0.742363 1.113256 0.138038 0.024 Uiso 1 1 calc R U . . .
C13 C 0.57672(16) 1.08911(15) 0.12414(14) 0.0245(4) Uani 1 1 d . . . . .
H13A H 0.566341 1.147887 0.095478 0.029 Uiso 1 1 calc R U . . .
C14 C 0.48788(15) 1.02488(16) 0.14037(15) 0.0259(4) Uani 1 1 d . . . . .
H14A H 0.416504 1.039935 0.124024 0.031 Uiso 1 1 calc R U . . .
C15 C 0.50303(14) 0.93823(15) 0.18064(15) 0.0239(4) Uani 1 1 d . . . . .
H15A H 0.441825 0.893386 0.191323 0.029 Uiso 1 1 calc R U . . .
C16 C 0.60707(14) 0.91671(14) 0.20539(14) 0.0191(3) Uani 1 1 d . . . . .
H16A H 0.616895 0.856612 0.232164 0.023 Uiso 1 1 calc R U . . .
C17 C 0.92608(15) 1.14282(13) 0.30831(13) 0.0193(3) Uani 1 1 d . . . . .
H17A H 0.864023 1.153122 0.346745 0.023 Uiso 1 1 calc R U . . .
H17B H 0.942826 1.206560 0.281347 0.023 Uiso 1 1 calc R U . . .
C18 C 1.02445(16) 1.13405(16) 0.38151(14) 0.0258(4) Uani 1 1 d . . . . .
H18A H 1.041119 1.198262 0.439932 0.039 Uiso 1 1 calc R U . . .
H18B H 1.087161 1.128017 0.344664 0.039 Uiso 1 1 calc R U . . .
H18C H 1.008646 1.070187 0.407245 0.039 Uiso 1 1 calc R U . . .
C19 C 0.79586(14) 0.96208(14) 0.40686(13) 0.0189(3) Uani 1 1 d . . . . .
H19A H 0.756846 1.022797 0.401610 0.023 Uiso 1 1 calc R U . . .
H19B H 0.864440 0.991404 0.455947 0.023 Uiso 1 1 calc R U . . .
C20 C 0.72623(17) 0.88394(16) 0.44907(15) 0.0274(4) Uani 1 1 d . . . . .
H20A H 0.719387 0.918054 0.520741 0.041 Uiso 1 1 calc R U . . .
H20B H 0.760446 0.819729 0.446989 0.041 Uiso 1 1 calc R U . . .
H20C H 0.653763 0.863404 0.406842 0.041 Uiso 1 1 calc R U . . .
O1A O 0.00068(10) 0.62351(10) 0.14402(9) 0.0215(3) Uani 1 1 d . . . . .
O2A O 0.07072(11) 0.39472(10) 0.44558(10) 0.0241(3) Uani 1 1 d . . . . .
N1A N 0.09934(12) 0.68084(12) 0.30911(11) 0.0169(3) Uani 1 1 d . . . . .
H1NA H 0.0605(18) 0.7267(18) 0.3342(17) 0.026(6) Uiso 1 1 d . . . . .
N2A N 0.12289(11) 0.52707(11) 0.20531(11) 0.0158(3) Uani 1 1 d . . . . .
N3A N 0.19051(11) 0.45168(11) 0.34556(11) 0.0156(3) Uani 1 1 d . . . . .
N4A N 0.09582(12) 0.56801(12) 0.42840(12) 0.0178(3) Uani 1 1 d . . . . .
H4NA H 0.054(2) 0.591(2) 0.470(2) 0.044(7) Uiso 1 1 d . . . . .
C1A C 0.16236(13) 0.63274(13) 0.37709(12) 0.0148(3) Uani 1 1 d . . . . .
C2A C 0.06725(13) 0.61106(13) 0.21342(13) 0.0168(3) Uani 1 1 d . . . . .
C3A C 0.20368(13) 0.53998(13) 0.29735(12) 0.0141(3) Uani 1 1 d . . . . .
C4A C 0.11393(13) 0.46529(14) 0.41018(13) 0.0171(3) Uani 1 1 d . . . . .
C5A C 0.25286(13) 0.71271(13) 0.45058(13) 0.0169(3) Uani 1 1 d . . . . .
C6A C 0.30312(15) 0.79816(14) 0.41943(15) 0.0230(4) Uani 1 1 d . . . . .
H6AA H 0.274387 0.811532 0.355999 0.028 Uiso 1 1 calc R U . . .
C7A C 0.39515(17) 0.86439(16) 0.48017(17) 0.0319(5) Uani 1 1 d . . . . .
H7AA H 0.429789 0.922087 0.457542 0.038 Uiso 1 1 calc R U . . .
C8A C 0.43660(17) 0.84694(17) 0.57318(17) 0.0355(5) Uani 1 1 d . . . . .
H8AA H 0.499792 0.892232 0.614550 0.043 Uiso 1 1 calc R U . . .
C9A C 0.38577(17) 0.76335(19) 0.60577(15) 0.0338(5) Uani 1 1 d . . . . .
H9AA H 0.413508 0.751850 0.670354 0.041 Uiso 1 1 calc R U . . .
C10A C 0.29406(16) 0.69558(16) 0.54480(14) 0.0260(4) Uani 1 1 d . . . . .
H10B H 0.259765 0.637808 0.567537 0.031 Uiso 1 1 calc R U . . .
C11A C 0.31890(13) 0.56908(13) 0.27840(13) 0.0159(3) Uani 1 1 d . . . . .
C12A C 0.33889(15) 0.61501(14) 0.19808(14) 0.0194(3) Uani 1 1 d . . . . .
H12B H 0.279584 0.623188 0.151065 0.023 Uiso 1 1 calc R U . . .
C13A C 0.44489(15) 0.64902(15) 0.18603(15) 0.0241(4) Uani 1 1 d . . . . .
H13B H 0.457845 0.680558 0.130968 0.029 Uiso 1 1 calc R U . . .
C14A C 0.53138(15) 0.63727(15) 0.25353(15) 0.0263(4) Uani 1 1 d . . . . .
H14B H 0.603890 0.660384 0.244875 0.032 Uiso 1 1 calc R U . . .
C15A C 0.51268(15) 0.59173(16) 0.33408(15) 0.0250(4) Uani 1 1 d . . . . .
H15B H 0.572339 0.583440 0.380628 0.030 Uiso 1 1 calc R U . . .
C16A C 0.40692(14) 0.55828(14) 0.34673(13) 0.0193(3) Uani 1 1 d . . . . .
H16B H 0.394343 0.527715 0.402479 0.023 Uiso 1 1 calc R U . . .
C17A C 0.11372(14) 0.44504(14) 0.10818(13) 0.0189(3) Uani 1 1 d . . . . .
H17C H 0.181523 0.413192 0.106961 0.023 Uiso 1 1 calc R U . . .
H17D H 0.106019 0.479170 0.049965 0.023 Uiso 1 1 calc R U . . .
C18A C 0.01748(16) 0.35644(15) 0.09292(15) 0.0264(4) Uani 1 1 d . . . . .
H18D H 0.016219 0.302289 0.027912 0.040 Uiso 1 1 calc R U . . .
H18E H -0.050240 0.386911 0.090274 0.040 Uiso 1 1 calc R U . . .
H18F H 0.024232 0.322833 0.150725 0.040 Uiso 1 1 calc R U . . .
C19A C 0.21779(14) 0.34494(13) 0.30348(13) 0.0185(3) Uani 1 1 d . . . . .
H19C H 0.253943 0.346226 0.242283 0.022 Uiso 1 1 calc R U . . .
H19D H 0.149582 0.292424 0.280023 0.022 Uiso 1 1 calc R U . . .
C20A C 0.29154(16) 0.30773(15) 0.38051(16) 0.0275(4) Uani 1 1 d . . . . .
H20D H 0.298649 0.232591 0.351348 0.041 Uiso 1 1 calc R U . . .
H20E H 0.260245 0.313971 0.444531 0.041 Uiso 1 1 calc R U . . .
H20F H 0.363563 0.352490 0.395613 0.041 Uiso 1 1 calc R U . . .
O1S O 0.22714(12) 1.05684(12) 0.19854(13) 0.0324(3) Uani 1 1 d . . . . .
H1S H 0.169(2) 1.068(2) 0.174(2) 0.053(9) Uiso 1 1 d . . . . .
C1S C 0.20646(17) 0.95137(18) 0.21133(18) 0.0351(5) Uani 1 1 d . . . . .
H1SB H 0.139880 0.943763 0.243503 0.042 Uiso 1 1 calc R U . . .
H1SC H 0.267945 0.940277 0.259079 0.042 Uiso 1 1 calc R U . . .
C2S C 0.19182(18) 0.86644(19) 0.1112(2) 0.0426(6) Uani 1 1 d . . . . .
H2SA H 0.177901 0.795328 0.124423 0.064 Uiso 1 1 calc R U . . .
H2SB H 0.258053 0.872548 0.079668 0.064 Uiso 1 1 calc R U . . .
H2SC H 0.129921 0.875898 0.064179 0.064 Uiso 1 1 calc R U . . .
O1SA O 0.2180(3) 0.3993(3) 0.6874(4) 0.0571(14) Uani 0.523(6) 1 d . U P A 1
H1SA H 0.170830 0.346623 0.661700 0.069 Uiso 0.523(6) 1 d R U P A 1
C1SA C 0.1811(13) 0.5001(9) 0.7141(12) 0.063(2) Uani 0.523(6) 1 d . U P A 1
H1SD H 0.119006 0.495044 0.752681 0.075 Uiso 0.523(6) 1 calc R U P A 1
H1SE H 0.157020 0.522626 0.650957 0.075 Uiso 0.523(6) 1 calc R U P A 1
C2SA C 0.2785(11) 0.5824(10) 0.7827(11) 0.069(3) Uani 0.523(6) 1 d . U P A 1
H2SD H 0.255946 0.653093 0.803272 0.103 Uiso 0.523(6) 1 calc R U P A 1
H2SE H 0.339043 0.587178 0.743388 0.103 Uiso 0.523(6) 1 calc R U P A 1
H2SF H 0.301859 0.558899 0.844567 0.103 Uiso 0.523(6) 1 calc R U P A 1
O1S' O 0.2275(3) 0.4600(4) 0.6422(3) 0.0503(15) Uani 0.477(6) 1 d . U P A 2
H1S' H 0.180948 0.430589 0.589234 0.060 Uiso 0.477(6) 1 d R U P A 2
C1S' C 0.1820(9) 0.5172(10) 0.7220(9) 0.045(2) Uani 0.477(6) 1 d . U P A 2
H1SF H 0.141473 0.466551 0.753911 0.053 Uiso 0.477(6) 1 calc R U P A 2
H1SG H 0.129622 0.558176 0.694007 0.053 Uiso 0.477(6) 1 calc R U P A 2
C2S' C 0.2652(9) 0.5916(14) 0.8011(10) 0.055(2) Uani 0.477(6) 1 d . U P A 2
H2SG H 0.233759 0.616603 0.864087 0.082 Uiso 0.477(6) 1 calc R U P A 2
H2SH H 0.291228 0.653228 0.775557 0.082 Uiso 0.477(6) 1 calc R U P A 2
H2SI H 0.326299 0.554696 0.816797 0.082 Uiso 0.477(6) 1 calc R U P A 2


_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 C2 1.241(2) . ?
O2 C4 1.231(2) . ?
N1 C2 1.352(2) . ?
N1 C1 1.443(2) . ?
N1 H1N 0.85(2) . ?
N2 C2 1.352(2) . ?
N2 C17 1.457(2) . ?
N2 C3 1.467(2) . ?
N3 C4 1.365(2) . ?
N3 C3 1.448(2) . ?
N3 C19 1.468(2) . ?
N4 C4 1.360(2) . ?
N4 C1 1.458(2) . ?
N4 H4N 0.87(2) . ?
C1 C5 1.512(2) . ?
C1 C3 1.592(2) . ?
C3 C11 1.511(2) . ?
C5 C10 1.389(2) . ?
C5 C6 1.392(2) . ?
C6 C7 1.387(2) . ?
C6 H6A 0.9500 . ?
C7 C8 1.386(3) . ?
C7 H7A 0.9500 . ?
C8 C9 1.381(3) . ?
C8 H8A 0.9500 . ?
C9 C10 1.389(2) . ?
C9 H9A 0.9500 . ?
C10 H10A 0.9500 . ?
C11 C16 1.389(2) . ?
C11 C12 1.390(2) . ?
C12 C13 1.389(2) . ?
C12 H12A 0.9500 . ?
C13 C14 1.377(3) . ?
C13 H13A 0.9500 . ?
C14 C15 1.385(3) . ?
C14 H14A 0.9500 . ?
C15 C16 1.385(2) . ?
C15 H15A 0.9500 . ?
C16 H16A 0.9500 . ?
C17 C18 1.516(3) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 C20 1.513(3) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
O1A C2A 1.230(2) . ?
O2A C4A 1.228(2) . ?
N1A C2A 1.367(2) . ?
N1A C1A 1.440(2) . ?
N1A H1NA 0.85(2) . ?
N2A C2A 1.356(2) . ?
N2A C17A 1.458(2) . ?
N2A C3A 1.464(2) . ?
N3A C4A 1.371(2) . ?
N3A C3A 1.449(2) . ?
N3A C19A 1.466(2) . ?
N4A C4A 1.350(2) . ?
N4A C1A 1.456(2) . ?
N4A H4NA 0.84(3) . ?
C1A C5A 1.511(2) . ?
C1A C3A 1.595(2) . ?
C3A C11A 1.513(2) . ?
C5A C6A 1.384(3) . ?
C5A C10A 1.390(3) . ?
C6A C7A 1.387(3) . ?
C6A H6AA 0.9500 . ?
C7A C8A 1.378(3) . ?
C7A H7AA 0.9500 . ?
C8A C9A 1.378(3) . ?
C8A H8AA 0.9500 . ?
C9A C10A 1.393(3) . ?
C9A H9AA 0.9500 . ?
C10A H10B 0.9500 . ?
C11A C12A 1.388(2) . ?
C11A C16A 1.392(2) . ?
C12A C13A 1.387(2) . ?
C12A H12B 0.9500 . ?
C13A C14A 1.376(3) . ?
C13A H13B 0.9500 . ?
C14A C15A 1.384(3) . ?
C14A H14B 0.9500 . ?
C15A C16A 1.385(2) . ?
C15A H15B 0.9500 . ?
C16A H16B 0.9500 . ?
C17A C18A 1.516(3) . ?
C17A H17C 0.9900 . ?
C17A H17D 0.9900 . ?
C18A H18D 0.9800 . ?
C18A H18E 0.9800 . ?
C18A H18F 0.9800 . ?
C19A C20A 1.511(2) . ?
C19A H19C 0.9900 . ?
C19A H19D 0.9900 . ?
C20A H20D 0.9800 . ?
C20A H20E 0.9800 . ?
C20A H20F 0.9800 . ?
O1S C1S 1.417(3) . ?
O1S H1S 0.81(3) . ?
C1S C2S 1.498(3) . ?
C1S H1SB 0.9900 . ?
C1S H1SC 0.9900 . ?
C2S H2SA 0.9800 . ?
C2S H2SB 0.9800 . ?
C2S H2SC 0.9800 . ?
O1SA C1SA 1.422(14) . ?
O1SA H1SA 0.8199 . ?
C1SA C2SA 1.552(18) . ?
C1SA H1SD 0.9900 . ?
C1SA H1SE 0.9900 . ?
C2SA H2SD 0.9800 . ?
C2SA H2SE 0.9800 . ?
C2SA H2SF 0.9800 . ?
O1S' C1S' 1.379(12) . ?
O1S' H1S' 0.8420 . ?
C1S' C2S' 1.463(17) . ?
C1S' H1SF 0.9900 . ?
C1S' H1SG 0.9900 . ?
C2S' H2SG 0.9800 . ?
C2S' H2SH 0.9800 . ?
C2S' H2SI 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
C2 N1 C1 111.23(14) . . ?
C2 N1 H1N 125.0(15) . . ?
C1 N1 H1N 121.1(15) . . ?
C2 N2 C17 122.52(14) . . ?
C2 N2 C3 112.00(13) . . ?
C17 N2 C3 125.45(13) . . ?
C4 N3 C3 109.98(13) . . ?
C4 N3 C19 121.46(14) . . ?
C3 N3 C19 124.97(13) . . ?
C4 N4 C1 112.02(13) . . ?
C4 N4 H4N 117.8(15) . . ?
C1 N4 H4N 122.9(15) . . ?
N1 C1 N4 112.80(13) . . ?
N1 C1 C5 112.60(13) . . ?
N4 C1 C5 112.74(13) . . ?
N1 C1 C3 101.23(12) . . ?
N4 C1 C3 99.60(12) . . ?
C5 C1 C3 116.78(13) . . ?
O1 C2 N1 126.10(15) . . ?
O1 C2 N2 124.77(15) . . ?
N1 C2 N2 109.13(14) . . ?
N3 C3 N2 113.43(13) . . ?
N3 C3 C11 112.78(13) . . ?
N2 C3 C11 111.93(13) . . ?
N3 C3 C1 102.12(12) . . ?
N2 C3 C1 99.80(12) . . ?
C11 C3 C1 115.84(13) . . ?
O2 C4 N4 125.87(15) . . ?
O2 C4 N3 124.68(15) . . ?
N4 C4 N3 109.46(14) . . ?
C10 C5 C6 119.19(15) . . ?
C10 C5 C1 120.92(15) . . ?
C6 C5 C1 119.88(15) . . ?
C7 C6 C5 120.23(16) . . ?
C7 C6 H6A 119.9 . . ?
C5 C6 H6A 119.9 . . ?
C8 C7 C6 120.32(17) . . ?
C8 C7 H7A 119.8 . . ?
C6 C7 H7A 119.8 . . ?
C9 C8 C7 119.62(16) . . ?
C9 C8 H8A 120.2 . . ?
C7 C8 H8A 120.2 . . ?
C8 C9 C10 120.36(17) . . ?
C8 C9 H9A 119.8 . . ?
C10 C9 H9A 119.8 . . ?
C5 C10 C9 120.27(16) . . ?
C5 C10 H10A 119.9 . . ?
C9 C10 H10A 119.9 . . ?
C16 C11 C12 119.26(15) . . ?
C16 C11 C3 119.76(14) . . ?
C12 C11 C3 120.89(15) . . ?
C13 C12 C11 120.04(17) . . ?
C13 C12 H12A 120.0 . . ?
C11 C12 H12A 120.0 . . ?
C14 C13 C12 120.44(17) . . ?
C14 C13 H13A 119.8 . . ?
C12 C13 H13A 119.8 . . ?
C13 C14 C15 119.70(17) . . ?
C13 C14 H14A 120.1 . . ?
C15 C14 H14A 120.1 . . ?
C16 C15 C14 120.24(17) . . ?
C16 C15 H15A 119.9 . . ?
C14 C15 H15A 119.9 . . ?
C15 C16 C11 120.29(16) . . ?
C15 C16 H16A 119.9 . . ?
C11 C16 H16A 119.9 . . ?
N2 C17 C18 111.73(14) . . ?
N2 C17 H17A 109.3 . . ?
C18 C17 H17A 109.3 . . ?
N2 C17 H17B 109.3 . . ?
C18 C17 H17B 109.3 . . ?
H17A C17 H17B 107.9 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N3 C19 C20 112.73(15) . . ?
N3 C19 H19A 109.0 . . ?
C20 C19 H19A 109.0 . . ?
N3 C19 H19B 109.0 . . ?
C20 C19 H19B 109.0 . . ?
H19A C19 H19B 107.8 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C2A N1A C1A 110.85(13) . . ?
C2A N1A H1NA 121.5(15) . . ?
C1A N1A H1NA 119.5(15) . . ?
C2A N2A C17A 121.76(14) . . ?
C2A N2A C3A 112.12(13) . . ?
C17A N2A C3A 125.31(13) . . ?
C4A N3A C3A 110.39(13) . . ?
C4A N3A C19A 120.79(14) . . ?
C3A N3A C19A 124.62(13) . . ?
C4A N4A C1A 113.21(14) . . ?
C4A N4A H4NA 120.9(18) . . ?
C1A N4A H4NA 125.7(18) . . ?
N1A C1A N4A 113.39(13) . . ?
N1A C1A C5A 112.67(14) . . ?
N4A C1A C5A 113.35(14) . . ?
N1A C1A C3A 102.18(12) . . ?
N4A C1A C3A 99.95(12) . . ?
C5A C1A C3A 114.14(13) . . ?
O1A C2A N2A 124.95(16) . . ?
O1A C2A N1A 125.62(15) . . ?
N2A C2A N1A 109.40(14) . . ?
N3A C3A N2A 113.77(13) . . ?
N3A C3A C11A 113.38(13) . . ?
N2A C3A C11A 112.32(13) . . ?
N3A C3A C1A 101.91(12) . . ?
N2A C3A C1A 100.21(12) . . ?
C11A C3A C1A 114.12(13) . . ?
O2A C4A N4A 126.55(15) . . ?
O2A C4A N3A 124.68(16) . . ?
N4A C4A N3A 108.77(14) . . ?
C6A C5A C10A 119.22(16) . . ?
C6A C5A C1A 119.62(15) . . ?
C10A C5A C1A 120.82(16) . . ?
C5A C6A C7A 120.46(18) . . ?
C5A C6A H6AA 119.8 . . ?
C7A C6A H6AA 119.8 . . ?
C8A C7A C6A 120.3(2) . . ?
C8A C7A H7AA 119.8 . . ?
C6A C7A H7AA 119.8 . . ?
C9A C8A C7A 119.56(19) . . ?
C9A C8A H8AA 120.2 . . ?
C7A C8A H8AA 120.2 . . ?
C8A C9A C10A 120.55(19) . . ?
C8A C9A H9AA 119.7 . . ?
C10A C9A H9AA 119.7 . . ?
C5A C10A C9A 119.83(19) . . ?
C5A C10A H10B 120.1 . . ?
C9A C10A H10B 120.1 . . ?
C12A C11A C16A 118.89(15) . . ?
C12A C11A C3A 120.77(15) . . ?
C16A C11A C3A 120.12(15) . . ?
C13A C12A C11A 120.42(17) . . ?
C13A C12A H12B 119.8 . . ?
C11A C12A H12B 119.8 . . ?
C14A C13A C12A 120.24(17) . . ?
C14A C13A H13B 119.9 . . ?
C12A C13A H13B 119.9 . . ?
C13A C14A C15A 119.97(17) . . ?
C13A C14A H14B 120.0 . . ?
C15A C14A H14B 120.0 . . ?
C14A C15A C16A 119.95(18) . . ?
C14A C15A H15B 120.0 . . ?
C16A C15A H15B 120.0 . . ?
C15A C16A C11A 120.52(17) . . ?
C15A C16A H16B 119.7 . . ?
C11A C16A H16B 119.7 . . ?
N2A C17A C18A 112.58(14) . . ?
N2A C17A H17C 109.1 . . ?
C18A C17A H17C 109.1 . . ?
N2A C17A H17D 109.1 . . ?
C18A C17A H17D 109.1 . . ?
H17C C17A H17D 107.8 . . ?
C17A C18A H18D 109.5 . . ?
C17A C18A H18E 109.5 . . ?
H18D C18A H18E 109.5 . . ?
C17A C18A H18F 109.5 . . ?
H18D C18A H18F 109.5 . . ?
H18E C18A H18F 109.5 . . ?
N3A C19A C20A 113.33(15) . . ?
N3A C19A H19C 108.9 . . ?
C20A C19A H19C 108.9 . . ?
N3A C19A H19D 108.9 . . ?
C20A C19A H19D 108.9 . . ?
H19C C19A H19D 107.7 . . ?
C19A C20A H20D 109.5 . . ?
C19A C20A H20E 109.5 . . ?
H20D C20A H20E 109.5 . . ?
C19A C20A H20F 109.5 . . ?
H20D C20A H20F 109.5 . . ?
H20E C20A H20F 109.5 . . ?
C1S O1S H1S 105(2) . . ?
O1S C1S C2S 112.79(18) . . ?
O1S C1S H1SB 109.0 . . ?
C2S C1S H1SB 109.0 . . ?
O1S C1S H1SC 109.0 . . ?
C2S C1S H1SC 109.0 . . ?
H1SB C1S H1SC 107.8 . . ?
C1S C2S H2SA 109.5 . . ?
C1S C2S H2SB 109.5 . . ?
H2SA C2S H2SB 109.5 . . ?
C1S C2S H2SC 109.5 . . ?
H2SA C2S H2SC 109.5 . . ?
H2SB C2S H2SC 109.5 . . ?
C1SA O1SA H1SA 116.3 . . ?
O1SA C1SA C2SA 107.0(11) . . ?
O1SA C1SA H1SD 110.3 . . ?
C2SA C1SA H1SD 110.3 . . ?
O1SA C1SA H1SE 110.3 . . ?
C2SA C1SA H1SE 110.3 . . ?
H1SD C1SA H1SE 108.6 . . ?
C1SA C2SA H2SD 109.5 . . ?
C1SA C2SA H2SE 109.5 . . ?
H2SD C2SA H2SE 109.5 . . ?
C1SA C2SA H2SF 109.5 . . ?
H2SD C2SA H2SF 109.5 . . ?
H2SE C2SA H2SF 109.5 . . ?
C1S' O1S' H1S' 112.3 . . ?
O1S' C1S' C2S' 111.6(8) . . ?
O1S' C1S' H1SF 109.3 . . ?
C2S' C1S' H1SF 109.3 . . ?
O1S' C1S' H1SG 109.3 . . ?
C2S' C1S' H1SG 109.3 . . ?
H1SF C1S' H1SG 108.0 . . ?
C1S' C2S' H2SG 109.5 . . ?
C1S' C2S' H2SH 109.5 . . ?
H2SG C2S' H2SH 109.5 . . ?
C1S' C2S' H2SI 109.5 . . ?
H2SG C2S' H2SI 109.5 . . ?
H2SH C2S' H2SI 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
C2 N1 C1 N4 -81.25(17) . . . . ?
C2 N1 C1 C5 149.75(14) . . . . ?
C2 N1 C1 C3 24.28(16) . . . . ?
C4 N4 C1 N1 126.18(15) . . . . ?
C4 N4 C1 C5 -104.89(16) . . . . ?
C4 N4 C1 C3 19.61(17) . . . . ?
C1 N1 C2 O1 166.17(15) . . . . ?
C1 N1 C2 N2 -14.45(18) . . . . ?
C17 N2 C2 O1 -6.3(2) . . . . ?
C3 N2 C2 O1 175.78(15) . . . . ?
C17 N2 C2 N1 174.33(14) . . . . ?
C3 N2 C2 N1 -3.61(18) . . . . ?
C4 N3 C3 N2 -83.02(16) . . . . ?
C19 N3 C3 N2 75.73(19) . . . . ?
C4 N3 C3 C11 148.41(14) . . . . ?
C19 N3 C3 C11 -52.8(2) . . . . ?
C4 N3 C3 C1 23.40(16) . . . . ?
C19 N3 C3 C1 -177.84(14) . . . . ?
C2 N2 C3 N3 125.43(14) . . . . ?
C17 N2 C3 N3 -52.4(2) . . . . ?
C2 N2 C3 C11 -105.56(15) . . . . ?
C17 N2 C3 C11 76.57(19) . . . . ?
C2 N2 C3 C1 17.56(16) . . . . ?
C17 N2 C3 C1 -160.31(14) . . . . ?
N1 C1 C3 N3 -140.46(12) . . . . ?
N4 C1 C3 N3 -24.72(14) . . . . ?
C5 C1 C3 N3 96.92(15) . . . . ?
N1 C1 C3 N2 -23.73(14) . . . . ?
N4 C1 C3 N2 92.01(13) . . . . ?
C5 C1 C3 N2 -146.35(13) . . . . ?
N1 C1 C3 C11 96.59(15) . . . . ?
N4 C1 C3 C11 -147.67(14) . . . . ?
C5 C1 C3 C11 -26.0(2) . . . . ?
C1 N4 C4 O2 174.01(16) . . . . ?
C1 N4 C4 N3 -6.32(19) . . . . ?
C3 N3 C4 O2 167.51(16) . . . . ?
C19 N3 C4 O2 7.9(3) . . . . ?
C3 N3 C4 N4 -12.16(19) . . . . ?
C19 N3 C4 N4 -171.79(15) . . . . ?
N1 C1 C5 C10 150.56(15) . . . . ?
N4 C1 C5 C10 21.5(2) . . . . ?
C3 C1 C5 C10 -92.93(18) . . . . ?
N1 C1 C5 C6 -30.4(2) . . . . ?
N4 C1 C5 C6 -159.38(14) . . . . ?
C3 C1 C5 C6 86.16(18) . . . . ?
C10 C5 C6 C7 -0.4(2) . . . . ?
C1 C5 C6 C7 -179.52(15) . . . . ?
C5 C6 C7 C8 0.3(3) . . . . ?
C6 C7 C8 C9 0.2(3) . . . . ?
C7 C8 C9 C10 -0.5(3) . . . . ?
C6 C5 C10 C9 0.0(2) . . . . ?
C1 C5 C10 C9 179.12(15) . . . . ?
C8 C9 C10 C5 0.5(3) . . . . ?
N3 C3 C11 C16 -36.1(2) . . . . ?
N2 C3 C11 C16 -165.47(14) . . . . ?
C1 C3 C11 C16 81.03(19) . . . . ?
N3 C3 C11 C12 147.36(15) . . . . ?
N2 C3 C11 C12 18.0(2) . . . . ?
C1 C3 C11 C12 -95.49(18) . . . . ?
C16 C11 C12 C13 1.3(3) . . . . ?
C3 C11 C12 C13 177.84(16) . . . . ?
C11 C12 C13 C14 0.1(3) . . . . ?
C12 C13 C14 C15 -1.0(3) . . . . ?
C13 C14 C15 C16 0.6(3) . . . . ?
C14 C15 C16 C11 0.8(3) . . . . ?
C12 C11 C16 C15 -1.7(3) . . . . ?
C3 C11 C16 C15 -178.32(16) . . . . ?
C2 N2 C17 C18 -80.84(19) . . . . ?
C3 N2 C17 C18 96.82(19) . . . . ?
C4 N3 C19 C20 -72.5(2) . . . . ?
C3 N3 C19 C20 131.06(17) . . . . ?
C2A N1A C1A N4A -85.18(17) . . . . ?
C2A N1A C1A C5A 144.37(14) . . . . ?
C2A N1A C1A C3A 21.44(17) . . . . ?
C4A N4A C1A N1A 122.72(15) . . . . ?
C4A N4A C1A C5A -107.17(16) . . . . ?
C4A N4A C1A C3A 14.71(17) . . . . ?
C17A N2A C2A O1A 4.3(3) . . . . ?
C3A N2A C2A O1A 174.52(16) . . . . ?
C17A N2A C2A N1A -173.80(14) . . . . ?
C3A N2A C2A N1A -3.55(19) . . . . ?
C1A N1A C2A O1A 169.42(16) . . . . ?
C1A N1A C2A N2A -12.53(19) . . . . ?
C4A N3A C3A N2A -83.49(16) . . . . ?
C19A N3A C3A N2A 73.47(19) . . . . ?
C4A N3A C3A C11A 146.53(14) . . . . ?
C19A N3A C3A C11A -56.5(2) . . . . ?
C4A N3A C3A C1A 23.43(16) . . . . ?
C19A N3A C3A C1A -179.62(14) . . . . ?
C2A N2A C3A N3A 123.80(15) . . . . ?
C17A N2A C3A N3A -66.36(19) . . . . ?
C2A N2A C3A C11A -105.69(15) . . . . ?
C17A N2A C3A C11A 64.1(2) . . . . ?
C2A N2A C3A C1A 15.83(16) . . . . ?
C17A N2A C3A C1A -174.33(14) . . . . ?
N1A C1A C3A N3A -138.53(13) . . . . ?
N4A C1A C3A N3A -21.77(15) . . . . ?
C5A C1A C3A N3A 99.54(15) . . . . ?
N1A C1A C3A N2A -21.36(15) . . . . ?
N4A C1A C3A N2A 95.39(13) . . . . ?
C5A C1A C3A N2A -143.29(14) . . . . ?
N1A C1A C3A C11A 98.87(15) . . . . ?
N4A C1A C3A C11A -144.38(14) . . . . ?
C5A C1A C3A C11A -23.06(19) . . . . ?
C1A N4A C4A O2A 178.34(17) . . . . ?
C1A N4A C4A N3A -1.0(2) . . . . ?
C3A N3A C4A O2A 165.26(16) . . . . ?
C19A N3A C4A O2A 7.3(3) . . . . ?
C3A N3A C4A N4A -15.39(19) . . . . ?
C19A N3A C4A N4A -173.36(14) . . . . ?
N1A C1A C5A C6A -31.9(2) . . . . ?
N4A C1A C5A C6A -162.41(15) . . . . ?
C3A C1A C5A C6A 84.02(19) . . . . ?
N1A C1A C5A C10A 154.84(16) . . . . ?
N4A C1A C5A C10A 24.4(2) . . . . ?
C3A C1A C5A C10A -89.20(19) . . . . ?
C10A C5A C6A C7A 1.6(3) . . . . ?
C1A C5A C6A C7A -171.72(17) . . . . ?
C5A C6A C7A C8A -1.1(3) . . . . ?
C6A C7A C8A C9A -0.2(3) . . . . ?
C7A C8A C9A C10A 1.0(3) . . . . ?
C6A C5A C10A C9A -0.8(3) . . . . ?
C1A C5A C10A C9A 172.40(17) . . . . ?
C8A C9A C10A C5A -0.5(3) . . . . ?
N3A C3A C11A C12A 152.19(15) . . . . ?
N2A C3A C11A C12A 21.5(2) . . . . ?
C1A C3A C11A C12A -91.71(18) . . . . ?
N3A C3A C11A C16A -33.1(2) . . . . ?
N2A C3A C11A C16A -163.84(14) . . . . ?
C1A C3A C11A C16A 82.96(18) . . . . ?
C16A C11A C12A C13A 0.3(2) . . . . ?
C3A C11A C12A C13A 175.04(15) . . . . ?
C11A C12A C13A C14A 0.2(3) . . . . ?
C12A C13A C14A C15A -0.3(3) . . . . ?
C13A C14A C15A C16A -0.1(3) . . . . ?
C14A C15A C16A C11A 0.6(3) . . . . ?
C12A C11A C16A C15A -0.7(3) . . . . ?
C3A C11A C16A C15A -175.47(16) . . . . ?
C2A N2A C17A C18A -85.57(19) . . . . ?
C3A N2A C17A C18A 105.52(18) . . . . ?
C4A N3A C19A C20A -77.5(2) . . . . ?
C3A N3A C19A C20A 127.81(17) . . . . ?

_refine_diff_density_max         0.681
_refine_diff_density_min         -0.294
_refine_diff_density_rms         0.059



####################################################################### 
# 
# 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_1b-MeCN
_database_code_depnum_ccdc_archive 'CCDC 2072854'
loop_
_audit_author_name
_audit_author_address
'Valentina Karnoukhova'
;A N Nesmeyanov Institute of Organoelement Compounds of Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2021-03-24 deposited with the CCDC.	2021-05-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H22 N4 O2, C2 H3 N'
_chemical_formula_sum            'C22 H25 N5 O2'
_chemical_formula_weight         391.47

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   12.6677(14)
_cell_length_b                   9.9394(11)
_cell_length_c                   16.7019(18)
_cell_angle_alpha                90
_cell_angle_beta                 101.334(2)
_cell_angle_gamma                90
_cell_volume                     2061.9(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    375
_cell_measurement_theta_min      3
_cell_measurement_theta_max      25

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.261
_exptl_crystal_F_000             832
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.290
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.084
_shelx_estimated_absorpt_T_min   0.976
_shelx_estimated_absorpt_T_max   0.983
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6892
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX DUO diffractometer'
_diffrn_detector_type            'Bruker APEX II CCD area detector'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            44091
_diffrn_reflns_av_unetI/netI     0.0368
_diffrn_reflns_av_R_equivalents  0.0630
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         1.640
_diffrn_reflns_theta_max         30.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             6006
_reflns_number_gt                4303
_reflns_threshold_expression     I>2σ(I)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015b)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0563P)²+0.6609P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6006
_refine_ls_number_parameters     273
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0756
_refine_ls_R_factor_gt           0.0474
_refine_ls_wR_factor_ref         0.1266
_refine_ls_wR_factor_gt          0.1106
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_restrained_S_all      1.016
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.07660(8) 1.05272(10) 0.17806(7) 0.0291(2) Uani 1 1 d . . . . .
O2 O -0.00740(8) 0.50502(10) 0.13546(6) 0.0257(2) Uani 1 1 d . . . . .
N1 N 0.09631(9) 0.85287(11) 0.24923(7) 0.0198(2) Uani 1 1 d . . . . .
H1N H 0.0704(15) 0.8862(19) 0.2895(12) 0.038(5) Uiso 1 1 d . . . . .
N2 N 0.19240(9) 0.88661(11) 0.15340(7) 0.0197(2) Uani 1 1 d . . . . .
N3 N 0.11793(9) 0.66385(11) 0.11893(7) 0.0200(2) Uani 1 1 d . . . . .
N4 N 0.10173(9) 0.60981(11) 0.24501(7) 0.0188(2) Uani 1 1 d . . . . .
H4N H 0.0559(15) 0.5959(18) 0.2765(11) 0.033(5) Uiso 1 1 d . . . . .
C1 C 0.16355(10) 0.73370(12) 0.25498(8) 0.0170(2) Uani 1 1 d . . . . .
C2 C 0.11769(11) 0.94172(13) 0.19266(8) 0.0213(3) Uani 1 1 d . . . . .
C3 C 0.20184(10) 0.74331(12) 0.17013(8) 0.0175(2) Uani 1 1 d . . . . .
C4 C 0.06333(11) 0.58601(13) 0.16327(8) 0.0202(3) Uani 1 1 d . . . . .
C5 C 0.25183(10) 0.73006(13) 0.33036(8) 0.0191(3) Uani 1 1 d . . . . .
C6 C 0.28090(12) 0.84491(14) 0.37681(9) 0.0247(3) Uani 1 1 d . . . . .
H6A H 0.241976 0.926163 0.363305 0.030 Uiso 1 1 calc R U . . .
C7 C 0.36657(13) 0.84149(17) 0.44287(9) 0.0317(3) Uani 1 1 d . . . . .
H7A H 0.386080 0.920594 0.474222 0.038 Uiso 1 1 calc R U . . .
C8 C 0.42345(13) 0.72449(19) 0.46332(9) 0.0350(4) Uani 1 1 d . . . . .
H8A H 0.482426 0.722868 0.508313 0.042 Uiso 1 1 calc R U . . .
C9 C 0.39428(13) 0.60922(17) 0.41800(10) 0.0337(4) Uani 1 1 d . . . . .
H9A H 0.432881 0.527944 0.432248 0.040 Uiso 1 1 calc R U . . .
C10 C 0.30914(12) 0.61188(15) 0.35203(9) 0.0266(3) Uani 1 1 d . . . . .
H10A H 0.289595 0.532257 0.321203 0.032 Uiso 1 1 calc R U . . .
C11 C 0.31338(10) 0.68940(13) 0.16964(8) 0.0194(3) Uani 1 1 d . . . . .
C12 C 0.40303(11) 0.76752(14) 0.19998(9) 0.0237(3) Uani 1 1 d . . . . .
H12A H 0.393989 0.856417 0.218409 0.028 Uiso 1 1 calc R U . . .
C13 C 0.50541(12) 0.71683(16) 0.20356(10) 0.0296(3) Uani 1 1 d . . . . .
H13A H 0.566460 0.770835 0.224532 0.036 Uiso 1 1 calc R U . . .
C14 C 0.51917(13) 0.58741(17) 0.17664(10) 0.0327(3) Uani 1 1 d . . . . .
H14A H 0.589576 0.552862 0.178697 0.039 Uiso 1 1 calc R U . . .
C15 C 0.43066(13) 0.50902(15) 0.14690(9) 0.0300(3) Uani 1 1 d . . . . .
H15A H 0.440068 0.420018 0.128778 0.036 Uiso 1 1 calc R U . . .
C16 C 0.32775(12) 0.55942(14) 0.14329(8) 0.0243(3) Uani 1 1 d . . . . .
H16A H 0.266896 0.504833 0.122720 0.029 Uiso 1 1 calc R U . . .
C17 C 0.22265(12) 0.95367(15) 0.08307(9) 0.0258(3) Uani 1 1 d . . . . .
H17A H 0.156545 0.978748 0.043656 0.031 Uiso 1 1 calc R U . . .
H17B H 0.263901 0.890011 0.055496 0.031 Uiso 1 1 calc R U . . .
C18 C 0.28981(14) 1.07869(17) 0.10708(11) 0.0379(4) Uani 1 1 d . . . . .
H18A H 0.305831 1.121586 0.058003 0.057 Uiso 1 1 calc R U . . .
H18B H 0.357276 1.053757 0.143697 0.057 Uiso 1 1 calc R U . . .
H18C H 0.249758 1.141600 0.135087 0.057 Uiso 1 1 calc R U . . .
C19 C 0.09784(12) 0.65959(14) 0.02995(8) 0.0244(3) Uani 1 1 d . . . . .
H19A H 0.086098 0.565111 0.011591 0.029 Uiso 1 1 calc R U . . .
H19B H 0.162056 0.693628 0.010842 0.029 Uiso 1 1 calc R U . . .
C20 C 0.00078(14) 0.74292(17) -0.00808(10) 0.0350(4) Uani 1 1 d . . . . .
H20A H -0.005388 0.745112 -0.067477 0.052 Uiso 1 1 calc R U . . .
H20B H 0.009318 0.834785 0.013541 0.052 Uiso 1 1 calc R U . . .
H20C H -0.064377 0.702782 0.005106 0.052 Uiso 1 1 calc R U . . .
N1S N 0.69913(16) 0.8189(2) 0.54938(14) 0.0760(7) Uani 1 1 d . . . . .
C1S C 0.75670(15) 0.7785(2) 0.60441(15) 0.0522(6) Uani 1 1 d . . . . .
C2S C 0.8305(2) 0.7290(2) 0.67411(19) 0.0740(8) Uani 1 1 d . . . . .
H2SA H 0.862496 0.804837 0.707859 0.111 Uiso 1 1 calc R U . . .
H2SB H 0.887532 0.677407 0.656062 0.111 Uiso 1 1 calc R U . . .
H2SC H 0.792193 0.670722 0.706180 0.111 Uiso 1 1 calc R U . . .


_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 C2 1.2238(16) . ?
O2 C4 1.2259(16) . ?
N1 C2 1.3588(17) . ?
N1 C1 1.4511(16) . ?
N1 H1N 0.870(19) . ?
N2 C2 1.3675(17) . ?
N2 C3 1.4519(16) . ?
N2 C17 1.4655(17) . ?
N3 C4 1.3516(17) . ?
N3 C19 1.4583(17) . ?
N3 C3 1.4586(16) . ?
N4 C4 1.3768(17) . ?
N4 C1 1.4512(16) . ?
N4 H4N 0.867(19) . ?
C1 C5 1.5112(18) . ?
C1 C3 1.5883(18) . ?
C3 C11 1.5126(18) . ?
C5 C6 1.3886(19) . ?
C5 C10 1.391(2) . ?
C6 C7 1.388(2) . ?
C6 H6A 0.9500 . ?
C7 C8 1.375(2) . ?
C7 H7A 0.9500 . ?
C8 C9 1.383(2) . ?
C8 H8A 0.9500 . ?
C9 C10 1.382(2) . ?
C9 H9A 0.9500 . ?
C10 H10A 0.9500 . ?
C11 C12 1.3868(19) . ?
C11 C16 1.3883(19) . ?
C12 C13 1.382(2) . ?
C12 H12A 0.9500 . ?
C13 C14 1.385(2) . ?
C13 H13A 0.9500 . ?
C14 C15 1.375(2) . ?
C14 H14A 0.9500 . ?
C15 C16 1.387(2) . ?
C15 H15A 0.9500 . ?
C16 H16A 0.9500 . ?
C17 C18 1.515(2) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 C20 1.515(2) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
N1S C1S 1.129(3) . ?
C1S C2S 1.430(3) . ?
C2S H2SA 0.9800 . ?
C2S H2SB 0.9800 . ?
C2S H2SC 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
C2 N1 C1 112.45(11) . . ?
C2 N1 H1N 116.5(12) . . ?
C1 N1 H1N 124.5(12) . . ?
C2 N2 C3 109.83(10) . . ?
C2 N2 C17 121.12(11) . . ?
C3 N2 C17 125.16(11) . . ?
C4 N3 C19 122.42(11) . . ?
C4 N3 C3 112.41(11) . . ?
C19 N3 C3 125.05(11) . . ?
C4 N4 C1 109.69(10) . . ?
C4 N4 H4N 115.2(12) . . ?
C1 N4 H4N 118.4(12) . . ?
N4 C1 N1 112.86(10) . . ?
N4 C1 C5 111.69(10) . . ?
N1 C1 C5 113.78(11) . . ?
N4 C1 C3 101.61(10) . . ?
N1 C1 C3 99.80(10) . . ?
C5 C1 C3 116.04(10) . . ?
O1 C2 N1 126.12(13) . . ?
O1 C2 N2 124.95(12) . . ?
N1 C2 N2 108.93(11) . . ?
N2 C3 N3 113.28(10) . . ?
N2 C3 C11 112.84(11) . . ?
N3 C3 C11 112.26(10) . . ?
N2 C3 C1 101.70(10) . . ?
N3 C3 C1 100.10(9) . . ?
C11 C3 C1 115.66(10) . . ?
O2 C4 N3 125.66(12) . . ?
O2 C4 N4 125.31(12) . . ?
N3 C4 N4 109.02(11) . . ?
C6 C5 C10 118.78(13) . . ?
C6 C5 C1 121.16(12) . . ?
C10 C5 C1 119.99(12) . . ?
C7 C6 C5 120.28(14) . . ?
C7 C6 H6A 119.9 . . ?
C5 C6 H6A 119.9 . . ?
C8 C7 C6 120.52(14) . . ?
C8 C7 H7A 119.7 . . ?
C6 C7 H7A 119.7 . . ?
C7 C8 C9 119.61(14) . . ?
C7 C8 H8A 120.2 . . ?
C9 C8 H8A 120.2 . . ?
C10 C9 C8 120.21(15) . . ?
C10 C9 H9A 119.9 . . ?
C8 C9 H9A 119.9 . . ?
C9 C10 C5 120.60(14) . . ?
C9 C10 H10A 119.7 . . ?
C5 C10 H10A 119.7 . . ?
C12 C11 C16 119.20(13) . . ?
C12 C11 C3 119.89(12) . . ?
C16 C11 C3 120.81(12) . . ?
C13 C12 C11 120.40(13) . . ?
C13 C12 H12A 119.8 . . ?
C11 C12 H12A 119.8 . . ?
C12 C13 C14 120.11(15) . . ?
C12 C13 H13A 119.9 . . ?
C14 C13 H13A 119.9 . . ?
C15 C14 C13 119.85(14) . . ?
C15 C14 H14A 120.1 . . ?
C13 C14 H14A 120.1 . . ?
C14 C15 C16 120.24(14) . . ?
C14 C15 H15A 119.9 . . ?
C16 C15 H15A 119.9 . . ?
C15 C16 C11 120.20(14) . . ?
C15 C16 H16A 119.9 . . ?
C11 C16 H16A 119.9 . . ?
N2 C17 C18 112.50(13) . . ?
N2 C17 H17A 109.1 . . ?
C18 C17 H17A 109.1 . . ?
N2 C17 H17B 109.1 . . ?
C18 C17 H17B 109.1 . . ?
H17A C17 H17B 107.8 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N3 C19 C20 112.10(12) . . ?
N3 C19 H19A 109.2 . . ?
C20 C19 H19A 109.2 . . ?
N3 C19 H19B 109.2 . . ?
C20 C19 H19B 109.2 . . ?
H19A C19 H19B 107.9 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
N1S C1S C2S 179.2(3) . . ?
C1S C2S H2SA 109.5 . . ?
C1S C2S H2SB 109.5 . . ?
H2SA C2S H2SB 109.5 . . ?
C1S C2S H2SC 109.5 . . ?
H2SA C2S H2SC 109.5 . . ?
H2SB C2S H2SC 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
C4 N4 C1 N1 80.40(13) . . . . ?
C4 N4 C1 C5 -149.91(11) . . . . ?
C4 N4 C1 C3 -25.57(13) . . . . ?
C2 N1 C1 N4 -125.97(12) . . . . ?
C2 N1 C1 C5 105.42(13) . . . . ?
C2 N1 C1 C3 -18.84(13) . . . . ?
C1 N1 C2 O1 -176.36(13) . . . . ?
C1 N1 C2 N2 4.29(16) . . . . ?
C3 N2 C2 O1 -164.83(13) . . . . ?
C17 N2 C2 O1 -5.9(2) . . . . ?
C3 N2 C2 N1 14.53(15) . . . . ?
C17 N2 C2 N1 173.41(12) . . . . ?
C2 N2 C3 N3 81.39(13) . . . . ?
C17 N2 C3 N3 -76.44(15) . . . . ?
C2 N2 C3 C11 -149.65(11) . . . . ?
C17 N2 C3 C11 52.52(17) . . . . ?
C2 N2 C3 C1 -25.11(13) . . . . ?
C17 N2 C3 C1 177.06(12) . . . . ?
C4 N3 C3 N2 -124.80(12) . . . . ?
C19 N3 C3 N2 59.11(16) . . . . ?
C4 N3 C3 C11 105.94(12) . . . . ?
C19 N3 C3 C11 -70.15(16) . . . . ?
C4 N3 C3 C1 -17.30(13) . . . . ?
C19 N3 C3 C1 166.62(12) . . . . ?
N4 C1 C3 N2 141.18(10) . . . . ?
N1 C1 C3 N2 25.20(11) . . . . ?
C5 C1 C3 N2 -97.47(12) . . . . ?
N4 C1 C3 N3 24.63(11) . . . . ?
N1 C1 C3 N3 -91.34(10) . . . . ?
C5 C1 C3 N3 145.99(11) . . . . ?
N4 C1 C3 C11 -96.19(12) . . . . ?
N1 C1 C3 C11 147.83(11) . . . . ?
C5 C1 C3 C11 25.16(16) . . . . ?
C19 N3 C4 O2 0.0(2) . . . . ?
C3 N3 C4 O2 -176.25(13) . . . . ?
C19 N3 C4 N4 178.50(12) . . . . ?
C3 N3 C4 N4 2.29(15) . . . . ?
C1 N4 C4 O2 -165.42(13) . . . . ?
C1 N4 C4 N3 16.04(15) . . . . ?
N4 C1 C5 C6 -144.61(12) . . . . ?
N1 C1 C5 C6 -15.40(17) . . . . ?
C3 C1 C5 C6 99.57(14) . . . . ?
N4 C1 C5 C10 38.58(16) . . . . ?
N1 C1 C5 C10 167.79(12) . . . . ?
C3 C1 C5 C10 -77.24(15) . . . . ?
C10 C5 C6 C7 0.9(2) . . . . ?
C1 C5 C6 C7 -175.99(12) . . . . ?
C5 C6 C7 C8 -0.2(2) . . . . ?
C6 C7 C8 C9 -0.5(2) . . . . ?
C7 C8 C9 C10 0.6(2) . . . . ?
C8 C9 C10 C5 0.0(2) . . . . ?
C6 C5 C10 C9 -0.8(2) . . . . ?
C1 C5 C10 C9 176.13(13) . . . . ?
N2 C3 C11 C12 36.56(17) . . . . ?
N3 C3 C11 C12 166.04(12) . . . . ?
C1 C3 C11 C12 -79.95(15) . . . . ?
N2 C3 C11 C16 -147.03(12) . . . . ?
N3 C3 C11 C16 -17.54(17) . . . . ?
C1 C3 C11 C16 96.46(14) . . . . ?
C16 C11 C12 C13 0.3(2) . . . . ?
C3 C11 C12 C13 176.79(13) . . . . ?
C11 C12 C13 C14 0.1(2) . . . . ?
C12 C13 C14 C15 -0.5(2) . . . . ?
C13 C14 C15 C16 0.4(2) . . . . ?
C14 C15 C16 C11 0.0(2) . . . . ?
C12 C11 C16 C15 -0.4(2) . . . . ?
C3 C11 C16 C15 -176.84(12) . . . . ?
C2 N2 C17 C18 71.75(17) . . . . ?
C3 N2 C17 C18 -132.75(14) . . . . ?
C4 N3 C19 C20 81.21(16) . . . . ?
C3 N3 C19 C20 -103.08(15) . . . . ?

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
N1 H1N O2 0.870(19) 2.00(2) 2.8491(15) 165.4(17) 2
N4 H4N O1 0.867(19) 2.020(19) 2.8665(15) 165.1(16) 2_545

_refine_diff_density_max         0.366
_refine_diff_density_min         -0.233
_refine_diff_density_rms         0.047



####################################################################### 
# 
# 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_1b-AcOH
_database_code_depnum_ccdc_archive 'CCDC 2072855'
loop_
_audit_author_name
_audit_author_address
'Valentina Karnoukhova'
;A N Nesmeyanov Institute of Organoelement Compounds of Russian Academy of Sciences
Russia
;
_audit_update_record             
;
2021-03-24 deposited with the CCDC.	2021-05-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H22 N4 O2, C2 H4 O2'
_chemical_formula_sum            'C22 H26 N4 O4'
_chemical_formula_weight         410.47

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   14.6755(14)
_cell_length_b                   17.8903(16)
_cell_length_c                   16.1564(15)
_cell_angle_alpha                90
_cell_angle_beta                 91.586(2)
_cell_angle_gamma                90
_cell_volume                     4240.2(7)
_cell_formula_units_Z            8
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    683
_cell_measurement_theta_min      3
_cell_measurement_theta_max      25

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_F_000             1744
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.180
_exptl_absorpt_coefficient_mu    0.090
_shelx_estimated_absorpt_T_min   0.976
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6784
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX DUO diffractometer'
_diffrn_detector_type            'Bruker APEX II CCD area detector'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            56043
_diffrn_reflns_av_unetI/netI     0.0774
_diffrn_reflns_av_R_equivalents  0.0940
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.172
_diffrn_reflns_theta_max         30.000
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             12373
_reflns_number_gt                7075
_reflns_threshold_expression     I>2σ(I)
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL (Sheldrick, 2015b)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0417P)²+0.9344P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         12373
_refine_ls_number_parameters     571
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1134
_refine_ls_R_factor_gt           0.0553
_refine_ls_wR_factor_ref         0.1302
_refine_ls_wR_factor_gt          0.1041
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_restrained_S_all      1.010
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 0.21451(8) 0.73523(7) 0.12333(7) 0.0261(3) Uani 1 1 d . . . . .
O2 O 0.02170(9) 0.95292(7) 0.30648(8) 0.0283(3) Uani 1 1 d . . . . .
N1 N 0.11556(10) 0.72169(9) 0.23044(9) 0.0218(3) Uani 1 1 d . . . . .
H1N H 0.1583(15) 0.7097(12) 0.2679(13) 0.040(6) Uiso 1 1 d . . . . .
N2 N 0.07539(10) 0.79432(9) 0.12428(9) 0.0229(3) Uani 1 1 d . . . . .
N3 N -0.02735(10) 0.87206(8) 0.20339(9) 0.0232(3) Uani 1 1 d . . . . .
N4 N 0.05990(10) 0.82810(8) 0.30619(10) 0.0222(3) Uani 1 1 d . . . . .
H4N H 0.0828(15) 0.8283(12) 0.3580(14) 0.043(7) Uiso 1 1 d . . . . .
C1 C 0.03716(11) 0.76082(10) 0.25950(10) 0.0200(4) Uani 1 1 d . . . . .
C2 C 0.14262(12) 0.75008(10) 0.15664(11) 0.0217(4) Uani 1 1 d . . . . .
C3 C -0.00419(12) 0.79719(10) 0.17638(10) 0.0213(4) Uani 1 1 d . . . . .
C4 C 0.01887(12) 0.88949(10) 0.27508(11) 0.0224(4) Uani 1 1 d . . . . .
C5 C -0.02656(12) 0.70968(10) 0.30515(10) 0.0203(4) Uani 1 1 d . . . . .
C6 C -0.03561(12) 0.63557(10) 0.28128(11) 0.0236(4) Uani 1 1 d . . . . .
H6A H 0.001530 0.616266 0.239044 0.028 Uiso 1 1 calc R U . . .
C7 C -0.09802(14) 0.58957(11) 0.31824(12) 0.0301(4) Uani 1 1 d . . . . .
H7A H -0.104120 0.539032 0.300921 0.036 Uiso 1 1 calc R U . . .
C8 C -0.15152(14) 0.61670(11) 0.38020(13) 0.0318(5) Uani 1 1 d . . . . .
H8A H -0.194615 0.584975 0.405429 0.038 Uiso 1 1 calc R U . . .
C9 C -0.14246(13) 0.68970(11) 0.40544(12) 0.0288(4) Uani 1 1 d . . . . .
H9A H -0.178672 0.708198 0.448770 0.035 Uiso 1 1 calc R U . . .
C10 C -0.08063(12) 0.73646(10) 0.36788(11) 0.0239(4) Uani 1 1 d . . . . .
H10A H -0.075195 0.787068 0.385121 0.029 Uiso 1 1 calc R U . . .
C11 C -0.08582(12) 0.75576(10) 0.14044(11) 0.0222(4) Uani 1 1 d . . . . .
C12 C -0.07529(13) 0.69939(11) 0.08262(11) 0.0256(4) Uani 1 1 d . . . . .
H12A H -0.016933 0.690114 0.060762 0.031 Uiso 1 1 calc R U . . .
C13 C -0.14886(14) 0.65665(11) 0.05657(12) 0.0299(4) Uani 1 1 d . . . . .
H13A H -0.140902 0.618246 0.016812 0.036 Uiso 1 1 calc R U . . .
C14 C -0.23403(14) 0.66941(11) 0.08797(13) 0.0339(5) Uani 1 1 d . . . . .
H14A H -0.284443 0.639535 0.070327 0.041 Uiso 1 1 calc R U . . .
C15 C -0.24561(13) 0.72566(12) 0.14501(13) 0.0328(5) Uani 1 1 d . . . . .
H15A H -0.304271 0.734995 0.166183 0.039 Uiso 1 1 calc R U . . .
C16 C -0.17204(12) 0.76853(11) 0.17147(12) 0.0269(4) Uani 1 1 d . . . . .
H16A H -0.180352 0.806972 0.211114 0.032 Uiso 1 1 calc R U . . .
C17 C 0.07992(13) 0.82418(11) 0.04013(11) 0.0261(4) Uani 1 1 d . . . . .
H17A H 0.017502 0.836533 0.019698 0.031 Uiso 1 1 calc R U . . .
H17B H 0.104423 0.785174 0.003416 0.031 Uiso 1 1 calc R U . . .
C18 C 0.13905(15) 0.89339(12) 0.03511(13) 0.0366(5) Uani 1 1 d . . . . .
H18A H 0.142709 0.909188 -0.022779 0.055 Uiso 1 1 calc R U . . .
H18B H 0.200372 0.882080 0.057214 0.055 Uiso 1 1 calc R U . . .
H18C H 0.112324 0.933641 0.067655 0.055 Uiso 1 1 calc R U . . .
C19 C -0.06592(13) 0.92911(11) 0.14780(12) 0.0283(4) Uani 1 1 d . . . . .
H19A H -0.085143 0.905053 0.094965 0.034 Uiso 1 1 calc R U . . .
H19B H -0.017845 0.965964 0.135471 0.034 Uiso 1 1 calc R U . . .
C20 C -0.14654(15) 0.96993(13) 0.18247(14) 0.0413(6) Uani 1 1 d . . . . .
H20A H -0.166984 1.008790 0.143445 0.062 Uiso 1 1 calc R U . . .
H20B H -0.128609 0.992997 0.235468 0.062 Uiso 1 1 calc R U . . .
H20C H -0.196313 0.934467 0.190967 0.062 Uiso 1 1 calc R U . . .
O1A O 0.22168(9) 0.70676(10) 0.37181(8) 0.0452(4) Uani 1 1 d . . . . .
O2A O 0.45888(9) 0.57896(7) 0.59403(8) 0.0286(3) Uani 1 1 d . . . . .
N1A N 0.30525(11) 0.76767(10) 0.47406(10) 0.0279(4) Uani 1 1 d . . . . .
H1NA H 0.2588(15) 0.7748(12) 0.5066(14) 0.043(7) Uiso 1 1 d . . . . .
N2A N 0.37639(11) 0.69073(10) 0.38945(9) 0.0300(4) Uani 1 1 d . . . . .
N3A N 0.49790(10) 0.65925(8) 0.48928(9) 0.0233(3) Uani 1 1 d . . . . .
N4A N 0.38957(10) 0.69325(9) 0.57360(9) 0.0216(3) Uani 1 1 d . . . . .
H4NA H 0.3546(16) 0.6903(13) 0.6159(14) 0.047(7) Uiso 1 1 d . . . . .
C1A C 0.39188(12) 0.75509(10) 0.51538(10) 0.0213(4) Uani 1 1 d . . . . .
C2A C 0.29439(13) 0.72007(13) 0.40832(11) 0.0325(5) Uani 1 1 d . . . . .
C3A C 0.45031(12) 0.71862(10) 0.44410(11) 0.0223(4) Uani 1 1 d . . . . .
C4A C 0.44827(12) 0.63861(10) 0.55618(11) 0.0226(4) Uani 1 1 d . . . . .
C5A C 0.43057(12) 0.82537(10) 0.55482(10) 0.0223(4) Uani 1 1 d . . . . .
C6A C 0.39742(14) 0.89515(11) 0.53167(12) 0.0324(5) Uani 1 1 d . . . . .
H6AA H 0.350408 0.899035 0.490274 0.039 Uiso 1 1 calc R U . . .
C7A C 0.43249(16) 0.95896(12) 0.56857(15) 0.0426(6) Uani 1 1 d . . . . .
H7AA H 0.408808 1.006455 0.552843 0.051 Uiso 1 1 calc R U . . .
C8A C 0.50131(15) 0.95447(12) 0.62782(14) 0.0402(5) Uani 1 1 d . . . . .
H8AA H 0.524974 0.998593 0.653080 0.048 Uiso 1 1 calc R U . . .
C9A C 0.53582(14) 0.88535(12) 0.65039(13) 0.0329(5) Uani 1 1 d . . . . .
H9AA H 0.584215 0.881962 0.690498 0.039 Uiso 1 1 calc R U . . .
C10A C 0.50002(12) 0.82099(11) 0.61467(11) 0.0253(4) Uani 1 1 d . . . . .
H10B H 0.523157 0.773549 0.631256 0.030 Uiso 1 1 calc R U . . .
C11A C 0.51410(12) 0.77017(10) 0.39923(11) 0.0220(4) Uani 1 1 d . . . . .
C12A C 0.48362(13) 0.80899(11) 0.32922(11) 0.0275(4) Uani 1 1 d . . . . .
H12B H 0.422291 0.803146 0.309930 0.033 Uiso 1 1 calc R U . . .
C13A C 0.54103(14) 0.85583(11) 0.28739(12) 0.0310(5) Uani 1 1 d . . . . .
H13B H 0.519181 0.881876 0.239592 0.037 Uiso 1 1 calc R U . . .
C14A C 0.62996(14) 0.86490(11) 0.31479(12) 0.0309(5) Uani 1 1 d . . . . .
H14B H 0.669816 0.896673 0.285619 0.037 Uiso 1 1 calc R U . . .
C15A C 0.66098(13) 0.82766(11) 0.38482(12) 0.0304(4) Uani 1 1 d . . . . .
H15B H 0.722178 0.834190 0.404166 0.037 Uiso 1 1 calc R U . . .
C16A C 0.60335(12) 0.78083(11) 0.42698(11) 0.0252(4) Uani 1 1 d . . . . .
H16B H 0.625151 0.755750 0.475427 0.030 Uiso 1 1 calc R U . . .
C17A C 0.38904(16) 0.65201(13) 0.31082(13) 0.0417(6) Uani 1 1 d . . . . .
H17C H 0.454088 0.654870 0.296437 0.050 Uiso 1 1 calc R U . . .
H17D H 0.353052 0.677873 0.266712 0.050 Uiso 1 1 calc R U . . .
C18A C 0.3605(2) 0.57090(16) 0.31336(17) 0.0732(10) Uani 1 1 d . . . . .
H18D H 0.370523 0.547740 0.259399 0.110 Uiso 1 1 calc R U . . .
H18E H 0.295756 0.567671 0.326190 0.110 Uiso 1 1 calc R U . . .
H18F H 0.396766 0.544681 0.356143 0.110 Uiso 1 1 calc R U . . .
C19A C 0.55772(14) 0.60415(11) 0.45143(13) 0.0348(5) Uani 1 1 d . . . . .
H19C H 0.576620 0.622938 0.396881 0.042 Uiso 1 1 calc R U . . .
H19D H 0.523535 0.557047 0.442142 0.042 Uiso 1 1 calc R U . . .
C20A C 0.64169(15) 0.58834(13) 0.50499(16) 0.0493(7) Uani 1 1 d . . . . .
H20D H 0.676540 0.547641 0.480440 0.074 Uiso 1 1 calc R U . . .
H20E H 0.623299 0.573771 0.560570 0.074 Uiso 1 1 calc R U . . .
H20F H 0.679613 0.633366 0.508675 0.074 Uiso 1 1 calc R U . . .
O1S O 0.11113(11) 0.63747(8) 0.97596(8) 0.0369(4) Uani 1 1 d . . . . .
O2S O 0.09230(10) 0.51590(8) 0.95310(9) 0.0352(3) Uani 1 1 d . . . . .
H2S H 0.0664(17) 0.5316(14) 0.9012(16) 0.060(8) Uiso 1 1 d . . . . .
C1S C 0.11633(13) 0.57325(11) 0.99972(12) 0.0278(4) Uani 1 1 d . . . . .
C2S C 0.15073(16) 0.55158(12) 1.08400(12) 0.0385(5) Uani 1 1 d . . . . .
H2SE H 0.178878 0.595043 1.111346 0.058 Uiso 1 1 calc R U . . .
H2SF H 0.196088 0.511697 1.079380 0.058 Uiso 1 1 calc R U . . .
H2SG H 0.099846 0.533740 1.116699 0.058 Uiso 1 1 calc R U . . .
O1SA O 0.29949(10) 0.63361(8) 0.72160(9) 0.0373(4) Uani 1 1 d . . . . .
O2SA O 0.35555(10) 0.51928(8) 0.70535(9) 0.0380(4) Uani 1 1 d . . . . .
H2SA H 0.3874(19) 0.5448(15) 0.6622(17) 0.074(9) Uiso 1 1 d . . . . .
C1SA C 0.30586(13) 0.56952(12) 0.74409(12) 0.0299(4) Uani 1 1 d . . . . .
C2SA C 0.26058(14) 0.53915(13) 0.81875(13) 0.0393(5) Uani 1 1 d . . . . .
H2SB H 0.226116 0.579064 0.845206 0.059 Uiso 1 1 calc R U . . .
H2SC H 0.306964 0.519791 0.857938 0.059 Uiso 1 1 calc R U . . .
H2SD H 0.218981 0.498693 0.802027 0.059 Uiso 1 1 calc R U . . .


_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 C2 1.227(2) . ?
O2 C4 1.243(2) . ?
N1 C2 1.365(2) . ?
N1 C1 1.437(2) . ?
N1 H1N 0.89(2) . ?
N2 C2 1.358(2) . ?
N2 C3 1.459(2) . ?
N2 C17 1.464(2) . ?
N3 C4 1.362(2) . ?
N3 C3 1.452(2) . ?
N3 C19 1.463(2) . ?
N4 C4 1.343(2) . ?
N4 C1 1.455(2) . ?
N4 H4N 0.89(2) . ?
C1 C5 1.514(2) . ?
C1 C3 1.597(2) . ?
C3 C11 1.511(2) . ?
C5 C6 1.386(2) . ?
C5 C10 1.390(2) . ?
C6 C7 1.380(3) . ?
C6 H6A 0.9500 . ?
C7 C8 1.378(3) . ?
C7 H7A 0.9500 . ?
C8 C9 1.373(3) . ?
C8 H8A 0.9500 . ?
C9 C10 1.386(3) . ?
C9 H9A 0.9500 . ?
C10 H10A 0.9500 . ?
C11 C12 1.386(3) . ?
C11 C16 1.393(3) . ?
C12 C13 1.379(3) . ?
C12 H12A 0.9500 . ?
C13 C14 1.381(3) . ?
C13 H13A 0.9500 . ?
C14 C15 1.378(3) . ?
C14 H14A 0.9500 . ?
C15 C16 1.382(3) . ?
C15 H15A 0.9500 . ?
C16 H16A 0.9500 . ?
C17 C18 1.515(3) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 C20 1.511(3) . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
O1A C2A 1.228(2) . ?
O2A C4A 1.237(2) . ?
N1A C2A 1.367(3) . ?
N1A C1A 1.437(2) . ?
N1A H1NA 0.88(2) . ?
N2A C2A 1.355(3) . ?
N2A C17A 1.463(2) . ?
N2A C3A 1.467(2) . ?
N3A C4A 1.371(2) . ?
N3A C3A 1.456(2) . ?
N3A C19A 1.465(2) . ?
N4A C4A 1.338(2) . ?
N4A C1A 1.453(2) . ?
N4A H4NA 0.87(2) . ?
C1A C5A 1.513(3) . ?
C1A C3A 1.594(2) . ?
C3A C11A 1.513(2) . ?
C5A C10A 1.388(3) . ?
C5A C6A 1.387(3) . ?
C6A C7A 1.381(3) . ?
C6A H6AA 0.9500 . ?
C7A C8A 1.375(3) . ?
C7A H7AA 0.9500 . ?
C8A C9A 1.381(3) . ?
C8A H8AA 0.9500 . ?
C9A C10A 1.385(3) . ?
C9A H9AA 0.9500 . ?
C10A H10B 0.9500 . ?
C11A C16A 1.386(2) . ?
C11A C12A 1.391(2) . ?
C12A C13A 1.379(3) . ?
C12A H12B 0.9500 . ?
C13A C14A 1.376(3) . ?
C13A H13B 0.9500 . ?
C14A C15A 1.379(3) . ?
C14A H14B 0.9500 . ?
C15A C16A 1.383(3) . ?
C15A H15B 0.9500 . ?
C16A H16B 0.9500 . ?
C17A C18A 1.511(3) . ?
C17A H17C 0.9900 . ?
C17A H17D 0.9900 . ?
C18A H18D 0.9800 . ?
C18A H18E 0.9800 . ?
C18A H18F 0.9800 . ?
C19A C20A 1.513(3) . ?
C19A H19C 0.9900 . ?
C19A H19D 0.9900 . ?
C20A H20D 0.9800 . ?
C20A H20E 0.9800 . ?
C20A H20F 0.9800 . ?
O1S C1S 1.213(2) . ?
O2S C1S 1.315(2) . ?
O2S H2S 0.95(3) . ?
C1S C2S 1.490(3) . ?
C2S H2SE 0.9800 . ?
C2S H2SF 0.9800 . ?
C2S H2SG 0.9800 . ?
O1SA C1SA 1.206(2) . ?
O2SA C1SA 1.325(2) . ?
O2SA H2SA 0.96(3) . ?
C1SA C2SA 1.495(3) . ?
C2SA H2SB 0.9800 . ?
C2SA H2SC 0.9800 . ?
C2SA H2SD 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
C2 N1 C1 111.04(15) . . ?
C2 N1 H1N 117.9(14) . . ?
C1 N1 H1N 117.0(14) . . ?
C2 N2 C3 112.52(14) . . ?
C2 N2 C17 121.26(15) . . ?
C3 N2 C17 125.48(14) . . ?
C4 N3 C3 110.59(14) . . ?
C4 N3 C19 122.51(16) . . ?
C3 N3 C19 123.28(15) . . ?
C4 N4 C1 112.86(15) . . ?
C4 N4 H4N 120.0(14) . . ?
C1 N4 H4N 124.3(14) . . ?
N1 C1 N4 113.48(14) . . ?
N1 C1 C5 112.07(15) . . ?
N4 C1 C5 112.53(14) . . ?
N1 C1 C3 102.29(13) . . ?
N4 C1 C3 100.10(14) . . ?
C5 C1 C3 115.49(14) . . ?
O1 C2 N2 125.58(17) . . ?
O1 C2 N1 125.25(17) . . ?
N2 C2 N1 109.10(15) . . ?
N3 C3 N2 113.80(15) . . ?
N3 C3 C11 112.23(14) . . ?
N2 C3 C11 113.56(15) . . ?
N3 C3 C1 102.11(13) . . ?
N2 C3 C1 100.32(13) . . ?
C11 C3 C1 113.71(14) . . ?
O2 C4 N4 125.73(17) . . ?
O2 C4 N3 124.49(17) . . ?
N4 C4 N3 109.78(16) . . ?
C6 C5 C10 118.72(16) . . ?
C6 C5 C1 119.86(15) . . ?
C10 C5 C1 121.31(16) . . ?
C7 C6 C5 120.65(17) . . ?
C7 C6 H6A 119.7 . . ?
C5 C6 H6A 119.7 . . ?
C8 C7 C6 120.20(18) . . ?
C8 C7 H7A 119.9 . . ?
C6 C7 H7A 119.9 . . ?
C9 C8 C7 119.89(18) . . ?
C9 C8 H8A 120.1 . . ?
C7 C8 H8A 120.1 . . ?
C8 C9 C10 120.19(18) . . ?
C8 C9 H9A 119.9 . . ?
C10 C9 H9A 119.9 . . ?
C9 C10 C5 120.34(17) . . ?
C9 C10 H10A 119.8 . . ?
C5 C10 H10A 119.8 . . ?
C12 C11 C16 118.77(17) . . ?
C12 C11 C3 120.92(16) . . ?
C16 C11 C3 119.98(16) . . ?
C13 C12 C11 120.53(18) . . ?
C13 C12 H12A 119.7 . . ?
C11 C12 H12A 119.7 . . ?
C12 C13 C14 120.34(19) . . ?
C12 C13 H13A 119.8 . . ?
C14 C13 H13A 119.8 . . ?
C13 C14 C15 119.73(19) . . ?
C13 C14 H14A 120.1 . . ?
C15 C14 H14A 120.1 . . ?
C16 C15 C14 120.15(19) . . ?
C16 C15 H15A 119.9 . . ?
C14 C15 H15A 119.9 . . ?
C15 C16 C11 120.48(19) . . ?
C15 C16 H16A 119.8 . . ?
C11 C16 H16A 119.8 . . ?
N2 C17 C18 112.87(16) . . ?
N2 C17 H17A 109.0 . . ?
C18 C17 H17A 109.0 . . ?
N2 C17 H17B 109.0 . . ?
C18 C17 H17B 109.0 . . ?
H17A C17 H17B 107.8 . . ?
C17 C18 H18A 109.5 . . ?
C17 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C17 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N3 C19 C20 113.78(16) . . ?
N3 C19 H19A 108.8 . . ?
C20 C19 H19A 108.8 . . ?
N3 C19 H19B 108.8 . . ?
C20 C19 H19B 108.8 . . ?
H19A C19 H19B 107.7 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C2A N1A C1A 110.24(16) . . ?
C2A N1A H1NA 118.6(15) . . ?
C1A N1A H1NA 115.7(14) . . ?
C2A N2A C17A 120.89(17) . . ?
C2A N2A C3A 112.29(15) . . ?
C17A N2A C3A 125.03(16) . . ?
C4A N3A C3A 109.51(14) . . ?
C4A N3A C19A 119.04(16) . . ?
C3A N3A C19A 124.48(15) . . ?
C4A N4A C1A 113.16(15) . . ?
C4A N4A H4NA 121.3(15) . . ?
C1A N4A H4NA 125.6(15) . . ?
N1A C1A N4A 112.56(15) . . ?
N1A C1A C5A 112.48(15) . . ?
N4A C1A C5A 112.04(14) . . ?
N1A C1A C3A 102.42(14) . . ?
N4A C1A C3A 100.29(14) . . ?
C5A C1A C3A 116.18(14) . . ?
O1A C2A N2A 125.6(2) . . ?
O1A C2A N1A 125.1(2) . . ?
N2A C2A N1A 109.32(16) . . ?
N3A C3A N2A 112.96(15) . . ?
N3A C3A C11A 112.97(15) . . ?
N2A C3A C11A 112.07(14) . . ?
N3A C3A C1A 101.33(13) . . ?
N2A C3A C1A 99.81(13) . . ?
C11A C3A C1A 116.67(15) . . ?
O2A C4A N4A 126.80(17) . . ?
O2A C4A N3A 124.03(17) . . ?
N4A C4A N3A 109.16(16) . . ?
C10A C5A C6A 118.95(18) . . ?
C10A C5A C1A 120.42(16) . . ?
C6A C5A C1A 120.62(17) . . ?
C7A C6A C5A 120.2(2) . . ?
C7A C6A H6AA 119.9 . . ?
C5A C6A H6AA 119.9 . . ?
C8A C7A C6A 120.7(2) . . ?
C8A C7A H7AA 119.7 . . ?
C6A C7A H7AA 119.7 . . ?
C7A C8A C9A 119.5(2) . . ?
C7A C8A H8AA 120.2 . . ?
C9A C8A H8AA 120.2 . . ?
C8A C9A C10A 120.1(2) . . ?
C8A C9A H9AA 119.9 . . ?
C10A C9A H9AA 119.9 . . ?
C9A C10A C5A 120.42(18) . . ?
C9A C10A H10B 119.8 . . ?
C5A C10A H10B 119.8 . . ?
C16A C11A C12A 118.31(17) . . ?
C16A C11A C3A 121.37(16) . . ?
C12A C11A C3A 120.32(16) . . ?
C13A C12A C11A 121.01(18) . . ?
C13A C12A H12B 119.5 . . ?
C11A C12A H12B 119.5 . . ?
C14A C13A C12A 120.07(18) . . ?
C14A C13A H13B 120.0 . . ?
C12A C13A H13B 120.0 . . ?
C13A C14A C15A 119.70(18) . . ?
C13A C14A H14B 120.2 . . ?
C15A C14A H14B 120.2 . . ?
C14A C15A C16A 120.28(18) . . ?
C14A C15A H15B 119.9 . . ?
C16A C15A H15B 119.9 . . ?
C15A C16A C11A 120.62(17) . . ?
C15A C16A H16B 119.7 . . ?
C11A C16A H16B 119.7 . . ?
N2A C17A C18A 112.90(18) . . ?
N2A C17A H17C 109.0 . . ?
C18A C17A H17C 109.0 . . ?
N2A C17A H17D 109.0 . . ?
C18A C17A H17D 109.0 . . ?
H17C C17A H17D 107.8 . . ?
C17A C18A H18D 109.5 . . ?
C17A C18A H18E 109.5 . . ?
H18D C18A H18E 109.5 . . ?
C17A C18A H18F 109.5 . . ?
H18D C18A H18F 109.5 . . ?
H18E C18A H18F 109.5 . . ?
N3A C19A C20A 112.03(18) . . ?
N3A C19A H19C 109.2 . . ?
C20A C19A H19C 109.2 . . ?
N3A C19A H19D 109.2 . . ?
C20A C19A H19D 109.2 . . ?
H19C C19A H19D 107.9 . . ?
C19A C20A H20D 109.5 . . ?
C19A C20A H20E 109.5 . . ?
H20D C20A H20E 109.5 . . ?
C19A C20A H20F 109.5 . . ?
H20D C20A H20F 109.5 . . ?
H20E C20A H20F 109.5 . . ?
C1S O2S H2S 111.5(15) . . ?
O1S C1S O2S 122.96(18) . . ?
O1S C1S C2S 123.52(19) . . ?
O2S C1S C2S 113.52(18) . . ?
C1S C2S H2SE 109.5 . . ?
C1S C2S H2SF 109.5 . . ?
H2SE C2S H2SF 109.5 . . ?
C1S C2S H2SG 109.5 . . ?
H2SE C2S H2SG 109.5 . . ?
H2SF C2S H2SG 109.5 . . ?
C1SA O2SA H2SA 107.7(16) . . ?
O1SA C1SA O2SA 122.80(18) . . ?
O1SA C1SA C2SA 123.8(2) . . ?
O2SA C1SA C2SA 113.40(19) . . ?
C1SA C2SA H2SB 109.5 . . ?
C1SA C2SA H2SC 109.5 . . ?
H2SB C2SA H2SC 109.5 . . ?
C1SA C2SA H2SD 109.5 . . ?
H2SB C2SA H2SD 109.5 . . ?
H2SC C2SA H2SD 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
C2 N1 C1 N4 -85.57(18) . . . . ?
C2 N1 C1 C5 145.61(15) . . . . ?
C2 N1 C1 C3 21.30(18) . . . . ?
C4 N4 C1 N1 124.28(16) . . . . ?
C4 N4 C1 C5 -107.14(17) . . . . ?
C4 N4 C1 C3 16.03(18) . . . . ?
C3 N2 C2 O1 176.17(17) . . . . ?
C17 N2 C2 O1 5.5(3) . . . . ?
C3 N2 C2 N1 -0.8(2) . . . . ?
C17 N2 C2 N1 -171.50(15) . . . . ?
C1 N1 C2 O1 168.91(17) . . . . ?
C1 N1 C2 N2 -14.1(2) . . . . ?
C4 N3 C3 N2 -87.93(17) . . . . ?
C19 N3 C3 N2 71.0(2) . . . . ?
C4 N3 C3 C11 141.36(15) . . . . ?
C19 N3 C3 C11 -59.7(2) . . . . ?
C4 N3 C3 C1 19.22(18) . . . . ?
C19 N3 C3 C1 178.17(15) . . . . ?
C2 N2 C3 N3 121.44(16) . . . . ?
C17 N2 C3 N3 -68.4(2) . . . . ?
C2 N2 C3 C11 -108.51(17) . . . . ?
C17 N2 C3 C11 61.7(2) . . . . ?
C2 N2 C3 C1 13.18(19) . . . . ?
C17 N2 C3 C1 -176.62(16) . . . . ?
N1 C1 C3 N3 -137.04(14) . . . . ?
N4 C1 C3 N3 -20.11(16) . . . . ?
C5 C1 C3 N3 100.96(16) . . . . ?
N1 C1 C3 N2 -19.75(17) . . . . ?
N4 C1 C3 N2 97.18(15) . . . . ?
C5 C1 C3 N2 -141.75(15) . . . . ?
N1 C1 C3 C11 101.83(16) . . . . ?
N4 C1 C3 C11 -141.23(15) . . . . ?
C5 C1 C3 C11 -20.2(2) . . . . ?
C1 N4 C4 O2 174.67(16) . . . . ?
C1 N4 C4 N3 -5.0(2) . . . . ?
C3 N3 C4 O2 170.08(17) . . . . ?
C19 N3 C4 O2 10.9(3) . . . . ?
C3 N3 C4 N4 -10.2(2) . . . . ?
C19 N3 C4 N4 -169.35(16) . . . . ?
N1 C1 C5 C6 -33.2(2) . . . . ?
N4 C1 C5 C6 -162.50(15) . . . . ?
C3 C1 C5 C6 83.4(2) . . . . ?
N1 C1 C5 C10 150.59(16) . . . . ?
N4 C1 C5 C10 21.3(2) . . . . ?
C3 C1 C5 C10 -92.81(19) . . . . ?
C10 C5 C6 C7 0.9(3) . . . . ?
C1 C5 C6 C7 -175.39(17) . . . . ?
C5 C6 C7 C8 -0.7(3) . . . . ?
C6 C7 C8 C9 -0.2(3) . . . . ?
C7 C8 C9 C10 1.0(3) . . . . ?
C8 C9 C10 C5 -0.8(3) . . . . ?
C6 C5 C10 C9 -0.2(3) . . . . ?
C1 C5 C10 C9 176.10(17) . . . . ?
N3 C3 C11 C12 153.49(16) . . . . ?
N2 C3 C11 C12 22.7(2) . . . . ?
C1 C3 C11 C12 -91.23(19) . . . . ?
N3 C3 C11 C16 -33.2(2) . . . . ?
N2 C3 C11 C16 -164.00(16) . . . . ?
C1 C3 C11 C16 82.1(2) . . . . ?
C16 C11 C12 C13 -0.2(3) . . . . ?
C3 C11 C12 C13 173.22(16) . . . . ?
C11 C12 C13 C14 -0.2(3) . . . . ?
C12 C13 C14 C15 0.7(3) . . . . ?
C13 C14 C15 C16 -0.8(3) . . . . ?
C14 C15 C16 C11 0.5(3) . . . . ?
C12 C11 C16 C15 0.0(3) . . . . ?
C3 C11 C16 C15 -173.45(17) . . . . ?
C2 N2 C17 C18 -81.5(2) . . . . ?
C3 N2 C17 C18 109.1(2) . . . . ?
C4 N3 C19 C20 -69.8(2) . . . . ?
C3 N3 C19 C20 133.66(19) . . . . ?
C2A N1A C1A N4A -82.82(19) . . . . ?
C2A N1A C1A C5A 149.47(16) . . . . ?
C2A N1A C1A C3A 24.02(19) . . . . ?
C4A N4A C1A N1A 120.59(17) . . . . ?
C4A N4A C1A C5A -111.46(17) . . . . ?
C4A N4A C1A C3A 12.40(18) . . . . ?
C17A N2A C2A O1A 13.7(3) . . . . ?
C3A N2A C2A O1A 179.18(19) . . . . ?
C17A N2A C2A N1A -165.65(17) . . . . ?
C3A N2A C2A N1A -0.2(2) . . . . ?
C1A N1A C2A O1A 164.42(19) . . . . ?
C1A N1A C2A N2A -16.2(2) . . . . ?
C4A N3A C3A N2A -80.21(18) . . . . ?
C19A N3A C3A N2A 70.0(2) . . . . ?
C4A N3A C3A C11A 151.27(15) . . . . ?
C19A N3A C3A C11A -58.5(2) . . . . ?
C4A N3A C3A C1A 25.66(18) . . . . ?
C19A N3A C3A C1A 175.90(16) . . . . ?
C2A N2A C3A N3A 120.96(17) . . . . ?
C17A N2A C3A N3A -74.3(2) . . . . ?
C2A N2A C3A C11A -110.05(18) . . . . ?
C17A N2A C3A C11A 54.7(2) . . . . ?
C2A N2A C3A C1A 14.12(19) . . . . ?
C17A N2A C3A C1A 178.89(18) . . . . ?
N1A C1A C3A N3A -137.91(14) . . . . ?
N4A C1A C3A N3A -21.85(16) . . . . ?
C5A C1A C3A N3A 99.10(17) . . . . ?
N1A C1A C3A N2A -21.91(17) . . . . ?
N4A C1A C3A N2A 94.15(15) . . . . ?
C5A C1A C3A N2A -144.91(15) . . . . ?
N1A C1A C3A C11A 98.99(17) . . . . ?
N4A C1A C3A C11A -144.95(15) . . . . ?
C5A C1A C3A C11A -24.0(2) . . . . ?
C1A N4A C4A O2A -178.07(17) . . . . ?
C1A N4A C4A N3A 3.1(2) . . . . ?
C3A N3A C4A O2A 161.73(17) . . . . ?
C19A N3A C4A O2A 9.6(3) . . . . ?
C3A N3A C4A N4A -19.4(2) . . . . ?
C19A N3A C4A N4A -171.53(16) . . . . ?
N1A C1A C5A C10A 163.04(16) . . . . ?
N4A C1A C5A C10A 35.1(2) . . . . ?
C3A C1A C5A C10A -79.4(2) . . . . ?
N1A C1A C5A C6A -17.1(2) . . . . ?
N4A C1A C5A C6A -145.09(17) . . . . ?
C3A C1A C5A C6A 100.5(2) . . . . ?
C10A C5A C6A C7A -0.8(3) . . . . ?
C1A C5A C6A C7A 179.35(18) . . . . ?
C5A C6A C7A C8A 0.8(3) . . . . ?
C6A C7A C8A C9A 0.2(3) . . . . ?
C7A C8A C9A C10A -1.3(3) . . . . ?
C8A C9A C10A C5A 1.3(3) . . . . ?
C6A C5A C10A C9A -0.3(3) . . . . ?
C1A C5A C10A C9A 179.59(16) . . . . ?
N3A C3A C11A C16A -26.9(2) . . . . ?
N2A C3A C11A C16A -155.93(17) . . . . ?
C1A C3A C11A C16A 89.9(2) . . . . ?
N3A C3A C11A C12A 153.95(16) . . . . ?
N2A C3A C11A C12A 25.0(2) . . . . ?
C1A C3A C11A C12A -89.2(2) . . . . ?
C16A C11A C12A C13A 1.2(3) . . . . ?
C3A C11A C12A C13A -179.63(17) . . . . ?
C11A C12A C13A C14A -0.1(3) . . . . ?
C12A C13A C14A C15A -0.8(3) . . . . ?
C13A C14A C15A C16A 0.6(3) . . . . ?
C14A C15A C16A C11A 0.5(3) . . . . ?
C12A C11A C16A C15A -1.4(3) . . . . ?
C3A C11A C16A C15A 179.44(17) . . . . ?
C2A N2A C17A C18A -84.0(3) . . . . ?
C3A N2A C17A C18A 112.4(2) . . . . ?
C4A N3A C19A C20A -72.7(2) . . . . ?
C3A N3A C19A C20A 139.68(18) . . . . ?

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
N1 H1N O1A 0.89(2) 1.90(2) 2.742(2) 159(2) .
O2SA H2SA O2A 0.96(3) 1.66(3) 2.6126(19) 169(3) .
N4A H4NA O1SA 0.87(2) 2.16(2) 2.963(2) 153(2) .
N4 H4N O1S 0.89(2) 2.03(2) 2.890(2) 160(2) 4_575
N1A H1NA O1 0.88(2) 2.02(2) 2.787(2) 145(2) 4_576
N4A H4NA O1 0.87(2) 2.46(2) 3.000(2) 121.3(18) 4_576
O2S H2S O2 0.95(3) 1.67(3) 2.619(2) 172(2) 4_576

_refine_diff_density_max         0.255
_refine_diff_density_min         -0.327
_refine_diff_density_rms         0.054



