# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2019

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

data_c
_database_code_depnum_ccdc_archive 'CCDC 1861294'
loop_
_audit_author_name
_audit_author_address
'Andrei Churakov'
;Institute of General and Inorganic Chemistry RAS
Russia
;
_audit_update_record             
;
2019-08-14 deposited with the CCDC.	2019-08-28 downloaded from the CCDC.
;


_vrf_PLAT111_ALERT_2_B           
;
PROBLEM: ADDSYM Detects New (Pseudo) Centre of Symmetry .        100 %Fit
RESPONSE: The structure is pseudosymmetric. The refinement in higher
symmetry space group P21/c results in abnormal ADP values of nitrogen
atoms and incorrect hydrazine H atoms positions. Moreover, refinement
in P21/c leads to more than twice higher R1 value (6.7 vs. 3.1 %).
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H24 O6, 2(H4 N2)'
_chemical_formula_sum            'C12 H32 N4 O6'
_chemical_formula_weight         328.41

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           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                   7.7920(7)
_cell_length_b                   14.2386(13)
_cell_length_c                   7.9049(7)
_cell_angle_alpha                90
_cell_angle_beta                 94.487(1)
_cell_angle_gamma                90
_cell_volume                     874.34(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    5434
_cell_measurement_theta_min      2.622
_cell_measurement_theta_max      30.013

_exptl_crystal_description       nugget
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.247
_exptl_crystal_F_000             360
_exptl_transmission_factor_min   0.6537
_exptl_transmission_factor_max   0.7461
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.099
_shelx_estimated_absorpt_T_min   0.962
_shelx_estimated_absorpt_T_max   0.981
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   'SADABS (Bruker, 2008)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker SMART APEX II'
_diffrn_measurement_method       ω
_diffrn_reflns_number            10331
_diffrn_reflns_av_unetI/netI     0.0221
_diffrn_reflns_av_R_equivalents  0.0161
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         2.585
_diffrn_reflns_theta_max         29.993
_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 0.977
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4966
_reflns_number_gt                4528
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.885
_reflns_Friedel_fraction_max     0.953
_reflns_Friedel_fraction_full    0.995

_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0556P)²+0.1026P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 2001 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.2(4)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         4966
_refine_ls_number_parameters     327
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0365
_refine_ls_R_factor_gt           0.0317
_refine_ls_wR_factor_ref         0.0858
_refine_ls_wR_factor_gt          0.0823
_refine_ls_goodness_of_fit_ref   0.968
_refine_ls_restrained_S_all      0.968
_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 0.27079(16) 0.64815(10) 0.63675(18) 0.0164(3) Uani 1 1 d . . . . .
O2 O 0.17686(16) 0.45816(10) 0.57772(16) 0.0170(3) Uani 1 1 d . . . . .
O3 O 0.44118(15) 0.32003(10) 0.62145(17) 0.0151(3) Uani 1 1 d . . . . .
O4 O 0.72866(16) 0.35022(10) 0.86559(17) 0.0160(3) Uani 1 1 d . . . . .
O5 O 0.82572(17) 0.54388(9) 0.92353(16) 0.0167(3) Uani 1 1 d . . . . .
O6 O 0.55745(15) 0.68206(9) 0.88057(17) 0.0155(3) Uani 1 1 d . . . . .
C1 C 0.4681(2) 0.75367(14) 0.7828(2) 0.0166(4) Uani 1 1 d . . . . .
C2 C 0.2817(2) 0.72511(13) 0.7514(2) 0.0163(4) Uani 1 1 d . . . . .
C3 C 0.0986(2) 0.61815(14) 0.5986(3) 0.0163(4) Uani 1 1 d . . . . .
C4 C 0.0978(2) 0.53341(15) 0.4839(2) 0.0173(4) Uani 1 1 d . . . . .
C5 C 0.1772(2) 0.37339(13) 0.4824(2) 0.0177(4) Uani 1 1 d . . . . .
C6 C 0.2635(2) 0.29790(14) 0.5922(3) 0.0165(4) Uani 1 1 d . . . . .
C7 C 0.5347(2) 0.24690(14) 0.7110(2) 0.0162(4) Uani 1 1 d . . . . .
C8 C 0.7189(2) 0.27681(14) 0.7430(2) 0.0175(4) Uani 1 1 d . . . . .
C9 C 0.8996(2) 0.38291(15) 0.9031(3) 0.0187(4) Uani 1 1 d . . . . .
C10 C 0.8964(2) 0.46612(16) 1.0193(3) 0.0177(4) Uani 1 1 d . . . . .
C11 C 0.8205(2) 0.62697(13) 1.0211(2) 0.0169(4) Uani 1 1 d . . . . .
C12 C 0.7354(2) 0.70346(14) 0.9117(3) 0.0171(4) Uani 1 1 d . . . . .
H11 H 0.475(3) 0.8113(19) 0.833(3) 0.017(6) Uiso 1 1 d . . . . .
H12 H 0.520(3) 0.7589(18) 0.677(3) 0.013(5) Uiso 1 1 d . . . . .
H21 H 0.233(3) 0.7088(18) 0.852(3) 0.009(5) Uiso 1 1 d . . . . .
H22 H 0.222(3) 0.7768(18) 0.700(3) 0.015(6) Uiso 1 1 d . . . . .
H31 H 0.030(3) 0.6709(19) 0.542(3) 0.025(7) Uiso 1 1 d . . . . .
H32 H 0.051(3) 0.601(2) 0.696(3) 0.017(5) Uiso 1 1 d . . . . .
H41 H -0.021(3) 0.5175(19) 0.435(3) 0.023(6) Uiso 1 1 d . . . . .
H42 H 0.166(3) 0.546(2) 0.386(3) 0.022(6) Uiso 1 1 d . . . . .
H51 H 0.061(3) 0.3566(17) 0.451(3) 0.009(5) Uiso 1 1 d . . . . .
H52 H 0.240(3) 0.383(2) 0.371(3) 0.023(7) Uiso 1 1 d . . . . .
H61 H 0.212(4) 0.293(2) 0.698(4) 0.023(7) Uiso 1 1 d . . . . .
H62 H 0.252(3) 0.2351(19) 0.537(3) 0.016(6) Uiso 1 1 d . . . . .
H71 H 0.526(3) 0.1896(19) 0.636(3) 0.021(6) Uiso 1 1 d . . . . .
H72 H 0.486(3) 0.233(2) 0.818(4) 0.023(7) Uiso 1 1 d . . . . .
H81 H 0.764(3) 0.301(2) 0.634(3) 0.026(7) Uiso 1 1 d . . . . .
H82 H 0.790(4) 0.220(2) 0.784(3) 0.022(6) Uiso 1 1 d . . . . .
H91 H 0.967(3) 0.337(2) 0.960(3) 0.025(7) Uiso 1 1 d . . . . .
H92 H 0.951(3) 0.399(2) 0.792(3) 0.028(7) Uiso 1 1 d . . . . .
H101 H 1.014(3) 0.482(2) 1.060(3) 0.031(7) Uiso 1 1 d . . . . .
H102 H 0.827(3) 0.452(2) 1.120(3) 0.020(6) Uiso 1 1 d . . . . .
H111 H 0.943(4) 0.653(2) 1.066(4) 0.036(8) Uiso 1 1 d . . . . .
H112 H 0.758(3) 0.6173(18) 1.113(3) 0.014(6) Uiso 1 1 d . . . . .
H121 H 0.789(4) 0.706(2) 0.802(4) 0.027(7) Uiso 1 1 d . . . . .
H122 H 0.750(3) 0.762(2) 0.969(3) 0.027(7) Uiso 1 1 d . . . . .
N1 N 0.6446(2) 0.55323(13) 0.5508(2) 0.0211(3) Uani 1 1 d . . . . .
H1 H 0.710(3) 0.5379(18) 0.640(3) 0.024(6) Uiso 1 1 d . . . . .
H2 H 0.533(3) 0.558(2) 0.589(3) 0.036(7) Uiso 1 1 d . . . . .
N2 N 0.6468(2) 0.47233(12) 0.4386(2) 0.0212(3) Uani 1 1 d . . . . .
H3 H 0.602(3) 0.4907(17) 0.337(3) 0.023(5) Uiso 1 1 d . . . . .
H4 H 0.574(3) 0.4344(18) 0.477(3) 0.011(5) Uiso 1 1 d . . . . .
N3 N 0.4143(2) 0.51482(12) 1.0702(2) 0.0240(3) Uani 1 1 d . . . . .
H5 H 0.313(3) 0.5303(18) 1.112(3) 0.026(6) Uiso 1 1 d . . . . .
H6 H 0.444(4) 0.574(3) 1.022(4) 0.059(10) Uiso 1 1 d . . . . .
N4 N 0.3686(2) 0.44431(12) 0.9420(2) 0.0201(3) Uani 1 1 d . . . . .
H7 H 0.327(3) 0.471(2) 0.848(3) 0.024(6) Uiso 1 1 d . . . . .
H8 H 0.470(3) 0.4210(18) 0.917(3) 0.021(6) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C3 1.418(2) . ?
O1 C2 1.420(2) . ?
O2 C4 1.417(2) . ?
O2 C5 1.423(2) . ?
O3 C6 1.421(2) . ?
O3 C7 1.427(2) . ?
O4 C9 1.420(2) . ?
O4 C8 1.423(2) . ?
O5 C11 1.414(2) . ?
O5 C10 1.427(2) . ?
O6 C12 1.422(2) . ?
O6 C1 1.427(2) . ?
C1 C2 1.510(3) . ?
C1 H11 0.91(3) . ?
C1 H12 0.96(3) . ?
C2 H21 0.94(2) . ?
C2 H22 0.95(3) . ?
C3 C4 1.509(3) . ?
C3 H31 1.01(3) . ?
C3 H32 0.91(2) . ?
C4 H41 1.00(2) . ?
C4 H42 0.99(3) . ?
C5 C6 1.506(3) . ?
C5 H51 0.95(2) . ?
C5 H52 1.05(2) . ?
C6 H61 0.96(3) . ?
C6 H62 1.00(3) . ?
C7 C8 1.500(3) . ?
C7 H71 1.01(3) . ?
C7 H72 0.98(3) . ?
C8 H81 1.02(3) . ?
C8 H82 1.02(3) . ?
C9 C10 1.500(3) . ?
C9 H91 0.93(3) . ?
C9 H92 1.02(3) . ?
C10 H101 0.98(3) . ?
C10 H102 1.02(2) . ?
C11 C12 1.511(3) . ?
C11 H111 1.05(3) . ?
C11 H112 0.92(2) . ?
C12 H121 1.00(3) . ?
C12 H122 0.95(3) . ?
N1 N2 1.454(2) . ?
N1 H1 0.86(2) . ?
N1 H2 0.95(3) . ?
N2 H3 0.89(2) . ?
N2 H4 0.86(2) . ?
N3 N4 1.451(2) . ?
N3 H5 0.91(2) . ?
N3 H6 0.96(4) . ?
N4 H7 0.88(2) . ?
N4 H8 0.89(2) . ?

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
C3 O1 C2 112.10(14) . . ?
C4 O2 C5 112.53(13) . . ?
C6 O3 C7 111.86(14) . . ?
C9 O4 C8 112.46(14) . . ?
C11 O5 C10 112.72(13) . . ?
C12 O6 C1 111.61(14) . . ?
O6 C1 C2 108.58(16) . . ?
O6 C1 H11 113.2(16) . . ?
C2 C1 H11 109.9(15) . . ?
O6 C1 H12 107.8(15) . . ?
C2 C1 H12 110.1(15) . . ?
H11 C1 H12 107(2) . . ?
O1 C2 C1 108.75(15) . . ?
O1 C2 H21 109.9(15) . . ?
C1 C2 H21 112.1(13) . . ?
O1 C2 H22 109.1(16) . . ?
C1 C2 H22 107.3(16) . . ?
H21 C2 H22 110(2) . . ?
O1 C3 C4 109.15(14) . . ?
O1 C3 H31 109.4(15) . . ?
C4 C3 H31 110.6(15) . . ?
O1 C3 H32 110.1(13) . . ?
C4 C3 H32 107.9(18) . . ?
H31 C3 H32 110(2) . . ?
O2 C4 C3 107.96(14) . . ?
O2 C4 H41 112.6(15) . . ?
C3 C4 H41 112.0(15) . . ?
O2 C4 H42 108.0(16) . . ?
C3 C4 H42 110.4(17) . . ?
H41 C4 H42 105.8(18) . . ?
O2 C5 C6 108.65(15) . . ?
O2 C5 H51 108.2(14) . . ?
C6 C5 H51 110.3(14) . . ?
O2 C5 H52 110.8(16) . . ?
C6 C5 H52 111.1(15) . . ?
H51 C5 H52 107.7(19) . . ?
O3 C6 C5 108.73(15) . . ?
O3 C6 H61 110.2(17) . . ?
C5 C6 H61 110.5(17) . . ?
O3 C6 H62 108.9(13) . . ?
C5 C6 H62 111.5(13) . . ?
H61 C6 H62 107(2) . . ?
O3 C7 C8 108.74(16) . . ?
O3 C7 H71 106.8(14) . . ?
C8 C7 H71 110.4(14) . . ?
O3 C7 H72 111.3(16) . . ?
C8 C7 H72 110.1(16) . . ?
H71 C7 H72 109(2) . . ?
O4 C8 C7 108.82(15) . . ?
O4 C8 H81 109.4(17) . . ?
C7 C8 H81 110.0(15) . . ?
O4 C8 H82 111.3(16) . . ?
C7 C8 H82 108.8(16) . . ?
H81 C8 H82 109(2) . . ?
O4 C9 C10 109.04(15) . . ?
O4 C9 H91 110.4(17) . . ?
C10 C9 H91 107.2(17) . . ?
O4 C9 H92 108.5(14) . . ?
C10 C9 H92 111.9(18) . . ?
H91 C9 H92 110(2) . . ?
O5 C10 C9 108.20(15) . . ?
O5 C10 H101 107.8(17) . . ?
C9 C10 H101 109.1(17) . . ?
O5 C10 H102 111.4(15) . . ?
C9 C10 H102 110.8(16) . . ?
H101 C10 H102 109.4(19) . . ?
O5 C11 C12 108.72(15) . . ?
O5 C11 H111 114.3(17) . . ?
C12 C11 H111 106.7(18) . . ?
O5 C11 H112 110.2(16) . . ?
C12 C11 H112 108.9(15) . . ?
H111 C11 H112 108(2) . . ?
O6 C12 C11 108.84(16) . . ?
O6 C12 H121 109.0(17) . . ?
C11 C12 H121 109.3(17) . . ?
O6 C12 H122 110.6(15) . . ?
C11 C12 H122 109.1(16) . . ?
H121 C12 H122 110(2) . . ?
N2 N1 H1 105.3(17) . . ?
N2 N1 H2 107.9(17) . . ?
H1 N1 H2 105(2) . . ?
N1 N2 H3 107.3(15) . . ?
N1 N2 H4 104.1(15) . . ?
H3 N2 H4 106(2) . . ?
N4 N3 H5 104.5(15) . . ?
N4 N3 H6 113(2) . . ?
H5 N3 H6 100(3) . . ?
N3 N4 H7 110.3(18) . . ?
N3 N4 H8 103.7(15) . . ?
H7 N4 H8 104(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
H1 N1 N2 H3 -167(2) . . . . ?
H1 N1 N2 H4 81(2) . . . . ?
H2 N1 N2 H3 82(2) . . . . ?
H2 N1 N2 H4 -31(2) . . . . ?
H5 N3 N4 H7 80(2) . . . . ?
H5 N3 N4 H8 -168(2) . . . . ?
H6 N3 N4 H7 -27(3) . . . . ?
H6 N3 N4 H8 84(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 H1 O5 0.86(2) 2.35(2) 3.169(2) 158(2) .
N1 H2 O1 0.95(3) 2.46(3) 3.329(2) 152(2) .
N2 H4 O3 0.86(2) 2.28(2) 3.118(2) 165.3(19) .
N3 H6 O6 0.96(4) 2.13(4) 3.070(2) 164(3) .
N4 H7 O2 0.88(2) 2.36(2) 3.145(2) 149(2) .
N4 H8 O4 0.89(2) 2.32(2) 3.209(2) 176(2) .

_refine_diff_density_max         0.399
_refine_diff_density_min         -0.170
_refine_diff_density_rms         0.039

####################################################################### 
# 
# 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_A
_database_code_depnum_ccdc_archive 'CCDC 1922854'
loop_
_audit_author_name
_audit_author_address
'Andrei Churakov'
;Institute of General and Inorganic Chemistry RAS
Russia
;
_audit_update_record             
;
2019-08-14 deposited with the CCDC.	2019-08-28 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         
;
C16 H36 N, C2 H3 O2, 0.902(H4 N2), 0.049(H4 O2)
;
_chemical_formula_sum            'C18 H42.80 N2.80 O2.10'
_chemical_formula_weight         332.16

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           56
_space_group_name_H-M_alt        'P c c n'
_space_group_name_Hall           '-P 2ab 2ac'

_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+1/2, z'
'-x, y+1/2, -z+1/2'
'x+1/2, -y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z'
'x, -y-1/2, z-1/2'
'-x-1/2, y, z-1/2'

_cell_length_a                   16.7939(4)
_cell_length_b                   17.0018(5)
_cell_length_c                   15.0341(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4292.63(18)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9411
_cell_measurement_theta_min      2.963
_cell_measurement_theta_max      30.515

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.028
_exptl_crystal_F_000             1498
_exptl_transmission_factor_min   0.9025
_exptl_transmission_factor_max   0.9705
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.067
_shelx_estimated_absorpt_T_min   0.980
_shelx_estimated_absorpt_T_max   0.987
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   'SADABS (Bruker, 2008)'
_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 SMART Photon II'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            38229
_diffrn_reflns_av_unetI/netI     0.0133
_diffrn_reflns_av_R_equivalents  0.0222
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.963
_diffrn_reflns_theta_max         26.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             4665
_reflns_number_gt                4086
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0634P)²+1.8354P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     difmap
_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         4665
_refine_ls_number_parameters     377
_refine_ls_number_restraints     9
_refine_ls_R_factor_all          0.0548
_refine_ls_R_factor_gt           0.0481
_refine_ls_wR_factor_ref         0.1295
_refine_ls_wR_factor_gt          0.1236
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.031
_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
N3 N 0.41502(5) 0.40791(6) 0.34859(6) 0.0198(2) Uani 1 1 d . . . . .
C11 C 0.32841(7) 0.38110(7) 0.35391(8) 0.0228(2) Uani 1 1 d . . . . .
C12 C 0.29095(8) 0.38656(9) 0.44539(9) 0.0320(3) Uani 1 1 d . . . . .
C13 C 0.20584(7) 0.35538(8) 0.44335(10) 0.0296(3) Uani 1 1 d . . . . .
C14 C 0.16350(9) 0.36761(15) 0.53152(12) 0.0561(5) Uani 1 1 d D . . . .
C21 C 0.42577(7) 0.48910(7) 0.38931(8) 0.0210(2) Uani 1 1 d . . . . .
C22 C 0.37721(7) 0.55399(7) 0.34682(9) 0.0264(3) Uani 1 1 d . . . . .
C23 C 0.38732(9) 0.62938(8) 0.40036(10) 0.0323(3) Uani 1 1 d . . . . .
C24 C 0.34762(11) 0.69952(9) 0.35711(15) 0.0492(4) Uani 1 1 d . . . . .
C31 C 0.43648(7) 0.40762(7) 0.25024(7) 0.0224(2) Uani 1 1 d . . . . .
C32 C 0.52256(7) 0.42873(8) 0.23074(8) 0.0262(3) Uani 1 1 d . . . . .
C33 C 0.54279(8) 0.41872(9) 0.13296(9) 0.0310(3) Uani 1 1 d . . . . .
C34 C 0.63092(9) 0.43391(10) 0.11605(10) 0.0395(3) Uani 1 1 d . . . . .
C41 C 0.46937(7) 0.35358(7) 0.40136(8) 0.0223(2) Uani 1 1 d . . . . .
C42 C 0.47653(8) 0.27060(7) 0.36542(9) 0.0272(3) Uani 1 1 d . . . . .
C43 C 0.53199(8) 0.22140(8) 0.42306(9) 0.0313(3) Uani 1 1 d . . . . .
C44 C 0.53358(10) 0.13612(9) 0.39290(10) 0.0384(3) Uani 1 1 d . . . . .
H111 H 0.2995(8) 0.4131(8) 0.3110(9) 0.023(3) Uiso 1 1 d . . . . .
H112 H 0.3292(9) 0.3263(9) 0.3291(10) 0.027(4) Uiso 1 1 d . . . . .
H121 H 0.3204(10) 0.3566(10) 0.4877(12) 0.044(5) Uiso 1 1 d . . . . .
H122 H 0.2904(11) 0.4422(12) 0.4664(13) 0.052(5) Uiso 1 1 d . . . . .
H131 H 0.2038(11) 0.3015(12) 0.4249(13) 0.056(5) Uiso 1 1 d . . . . .
H132 H 0.1763(11) 0.3827(11) 0.3959(12) 0.043(5) Uiso 1 1 d . . . . .
H141 H 0.152(2) 0.4259(12) 0.539(2) 0.147(14) Uiso 1 1 d D . . . .
H142 H 0.1951(13) 0.3481(14) 0.5822(14) 0.087(8) Uiso 1 1 d D . . . .
H143 H 0.1110(10) 0.3410(11) 0.5349(14) 0.060(6) Uiso 1 1 d D . . . .
H211 H 0.4822(9) 0.4998(8) 0.3858(9) 0.023(3) Uiso 1 1 d . . . . .
H212 H 0.4120(8) 0.4827(8) 0.4500(9) 0.019(3) Uiso 1 1 d . . . . .
H221 H 0.3955(10) 0.5632(10) 0.2866(11) 0.037(4) Uiso 1 1 d . . . . .
H222 H 0.3218(11) 0.5409(10) 0.3420(11) 0.042(4) Uiso 1 1 d . . . . .
H231 H 0.3668(12) 0.6204(11) 0.4581(14) 0.055(5) Uiso 1 1 d . . . . .
H232 H 0.4427(11) 0.6405(10) 0.4082(12) 0.044(5) Uiso 1 1 d . . . . .
H241 H 0.2910(15) 0.6894(14) 0.3478(16) 0.077(7) Uiso 1 1 d . . . . .
H242 H 0.3723(15) 0.7138(15) 0.2951(18) 0.087(8) Uiso 1 1 d . . . . .
H243 H 0.3524(11) 0.7467(13) 0.3949(13) 0.059(5) Uiso 1 1 d . . . . .
H311 H 0.4243(8) 0.3545(8) 0.2285(9) 0.022(3) Uiso 1 1 d . . . . .
H312 H 0.4001(9) 0.4435(9) 0.2220(10) 0.024(3) Uiso 1 1 d . . . . .
H321 H 0.5332(9) 0.4836(10) 0.2480(11) 0.035(4) Uiso 1 1 d . . . . .
H322 H 0.5581(10) 0.3956(10) 0.2651(11) 0.038(4) Uiso 1 1 d . . . . .
H331 H 0.5287(9) 0.3651(10) 0.1158(11) 0.036(4) Uiso 1 1 d . . . . .
H332 H 0.5089(11) 0.4538(11) 0.0991(12) 0.044(5) Uiso 1 1 d . . . . .
H341 H 0.6656(13) 0.3935(13) 0.1507(14) 0.064(6) Uiso 1 1 d . . . . .
H342 H 0.6457(12) 0.4858(13) 0.1360(13) 0.057(5) Uiso 1 1 d . . . . .
H343 H 0.6420(13) 0.4293(13) 0.0547(16) 0.066(6) Uiso 1 1 d . . . . .
H411 H 0.4484(8) 0.3533(8) 0.4622(10) 0.023(3) Uiso 1 1 d . . . . .
H412 H 0.5210(9) 0.3800(9) 0.4037(9) 0.023(3) Uiso 1 1 d . . . . .
H421 H 0.4250(10) 0.2460(10) 0.3624(10) 0.037(4) Uiso 1 1 d . . . . .
H422 H 0.4971(10) 0.2709(9) 0.3033(11) 0.038(4) Uiso 1 1 d . . . . .
H431 H 0.5844(11) 0.2448(11) 0.4203(12) 0.048(5) Uiso 1 1 d . . . . .
H432 H 0.5147(10) 0.2250(10) 0.4862(12) 0.045(5) Uiso 1 1 d . . . . .
H441 H 0.5487(13) 0.1336(13) 0.3288(15) 0.065(6) Uiso 1 1 d . . . . .
H442 H 0.5711(13) 0.1032(13) 0.4285(14) 0.065(6) Uiso 1 1 d . . . . .
H443 H 0.4773(12) 0.1131(12) 0.3983(13) 0.055(5) Uiso 1 1 d . . . . .
C1 C 0.19008(8) 0.51023(10) 0.14762(9) 0.0381(3) Uani 1 1 d . . . . .
C10 C 0.22895(10) 0.58984(13) 0.13575(12) 0.0553(5) Uani 1 1 d . . . . .
H103 H 0.268920 0.597712 0.182394 0.121(10) Uiso 1 1 calc R . . . .
H102 H 0.188389 0.631118 0.139835 0.115(10) Uiso 1 1 calc R . . . .
H101 H 0.254712 0.592231 0.077320 0.140(12) Uiso 1 1 calc R . . . .
O1 O 0.22304(8) 0.46257(8) 0.19950(8) 0.0589(4) Uani 1 1 d . . . . .
O2 O 0.12678(5) 0.49783(6) 0.10489(6) 0.0368(3) Uani 1 1 d . . . . .
N1 N 0.15686(11) 0.29998(13) 0.20005(13) 0.0564(5) Uani 0.902(4) 1 d D . P A 1
H11 H 0.1849(13) 0.3424(11) 0.2092(15) 0.050(6) Uiso 0.902(4) 1 d D . P A 1
H12 H 0.185(2) 0.275(2) 0.161(2) 0.139(15) Uiso 0.902(4) 1 d D . P A 1
N2 N 0.08523(10) 0.32687(11) 0.15207(12) 0.0507(5) Uani 0.902(4) 1 d D . P A 1
H21 H 0.0916(12) 0.3722(10) 0.1369(13) 0.039(5) Uiso 0.902(4) 1 d D . P A 1
H22 H 0.0521(14) 0.3296(16) 0.1912(15) 0.076(8) Uiso 0.902(4) 1 d D . P A 1
O10 O 0.2034(5) 0.2845(5) 0.2307(6) 0.022(3) Uiso 0.098(4) 1 d . . P A 2
H1 H 0.208443 0.330766 0.222721 0.034 Uiso 0.098(4) 1 d R U P A 2
H2 H 0.241353 0.256126 0.230691 0.034 Uiso 0.098(4) 1 d 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
N3 C21 1.5208(14) . ?
N3 C41 1.5217(14) . ?
N3 C31 1.5218(14) . ?
N3 C11 1.5265(14) . ?
C11 C12 1.5152(17) . ?
C11 H111 0.974(14) . ?
C11 H112 1.004(15) . ?
C12 C13 1.5248(16) . ?
C12 H121 0.953(18) . ?
C12 H122 1.00(2) . ?
C13 C14 1.519(2) . ?
C13 H131 0.96(2) . ?
C13 H132 0.985(18) . ?
C14 H141 1.017(19) . ?
C14 H142 0.986(17) . ?
C14 H143 0.992(16) . ?
C21 C22 1.5133(17) . ?
C21 H211 0.967(14) . ?
C21 H212 0.947(14) . ?
C22 C23 1.5231(17) . ?
C22 H221 0.968(17) . ?
C22 H222 0.959(18) . ?
C23 C24 1.513(2) . ?
C23 H231 0.95(2) . ?
C23 H232 0.957(19) . ?
C24 H241 0.98(2) . ?
C24 H242 1.05(3) . ?
C24 H243 0.99(2) . ?
C31 C32 1.5180(17) . ?
C31 H311 0.982(14) . ?
C31 H312 0.963(15) . ?
C32 C33 1.5184(17) . ?
C32 H321 0.985(17) . ?
C32 H322 0.970(18) . ?
C33 C34 1.524(2) . ?
C33 H331 0.977(17) . ?
C33 H332 0.969(19) . ?
C34 H341 1.04(2) . ?
C34 H342 0.96(2) . ?
C34 H343 0.94(2) . ?
C41 C42 1.5155(17) . ?
C41 H411 0.980(15) . ?
C41 H412 0.977(15) . ?
C42 C43 1.5224(17) . ?
C42 H421 0.962(17) . ?
C42 H422 0.996(17) . ?
C43 C44 1.520(2) . ?
C43 H431 0.967(19) . ?
C43 H432 0.994(18) . ?
C44 H441 1.00(2) . ?
C44 H442 1.00(2) . ?
C44 H443 1.03(2) . ?
C1 O1 1.2535(19) . ?
C1 O2 1.2597(17) . ?
C1 C10 1.513(3) . ?
C10 H103 0.9800 . ?
C10 H102 0.9800 . ?
C10 H101 0.9800 . ?
N1 N2 1.475(2) . ?
N1 H11 0.873(16) . ?
N1 H12 0.862(19) . ?
N2 H21 0.811(16) . ?
N2 H22 0.811(17) . ?
O10 H1 0.8001 . ?
O10 H2 0.7999 . ?

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
C21 N3 C41 105.66(8) . . ?
C21 N3 C31 111.47(9) . . ?
C41 N3 C31 111.26(9) . . ?
C21 N3 C11 111.29(9) . . ?
C41 N3 C11 111.28(9) . . ?
C31 N3 C11 106.00(8) . . ?
C12 C11 N3 115.15(9) . . ?
C12 C11 H111 111.1(8) . . ?
N3 C11 H111 105.9(8) . . ?
C12 C11 H112 113.6(8) . . ?
N3 C11 H112 104.2(8) . . ?
H111 C11 H112 106.2(12) . . ?
C11 C12 C13 110.46(11) . . ?
C11 C12 H121 111.0(11) . . ?
C13 C12 H121 108.3(10) . . ?
C11 C12 H122 110.4(11) . . ?
C13 C12 H122 109.2(11) . . ?
H121 C12 H122 107.4(15) . . ?
C14 C13 C12 111.95(12) . . ?
C14 C13 H131 111.5(12) . . ?
C12 C13 H131 111.8(12) . . ?
C14 C13 H132 109.3(10) . . ?
C12 C13 H132 108.8(10) . . ?
H131 C13 H132 103.0(16) . . ?
C13 C14 H141 109(2) . . ?
C13 C14 H142 112.1(15) . . ?
H141 C14 H142 111(3) . . ?
C13 C14 H143 113.5(12) . . ?
H141 C14 H143 105(2) . . ?
H142 C14 H143 106.6(19) . . ?
C22 C21 N3 115.33(9) . . ?
C22 C21 H211 111.6(8) . . ?
N3 C21 H211 105.4(8) . . ?
C22 C21 H212 111.0(8) . . ?
N3 C21 H212 104.8(8) . . ?
H211 C21 H212 108.2(12) . . ?
C21 C22 C23 109.29(10) . . ?
C21 C22 H221 110.0(10) . . ?
C23 C22 H221 108.8(10) . . ?
C21 C22 H222 112.7(10) . . ?
C23 C22 H222 110.0(10) . . ?
H221 C22 H222 105.9(14) . . ?
C24 C23 C22 112.77(12) . . ?
C24 C23 H231 111.2(12) . . ?
C22 C23 H231 108.0(12) . . ?
C24 C23 H232 109.0(11) . . ?
C22 C23 H232 109.9(11) . . ?
H231 C23 H232 105.9(16) . . ?
C23 C24 H241 110.6(14) . . ?
C23 C24 H242 113.0(14) . . ?
H241 C24 H242 107(2) . . ?
C23 C24 H243 110.9(12) . . ?
H241 C24 H243 107.8(18) . . ?
H242 C24 H243 106.9(18) . . ?
C32 C31 N3 114.35(9) . . ?
C32 C31 H311 110.6(8) . . ?
N3 C31 H311 106.0(8) . . ?
C32 C31 H312 111.7(9) . . ?
N3 C31 H312 106.0(9) . . ?
H311 C31 H312 107.7(12) . . ?
C31 C32 C33 111.94(10) . . ?
C31 C32 H321 110.2(9) . . ?
C33 C32 H321 108.7(10) . . ?
C31 C32 H322 110.3(10) . . ?
C33 C32 H322 108.2(10) . . ?
H321 C32 H322 107.4(13) . . ?
C32 C33 C34 111.10(11) . . ?
C32 C33 H331 107.8(10) . . ?
C34 C33 H331 110.5(10) . . ?
C32 C33 H332 108.0(11) . . ?
C34 C33 H332 112.3(11) . . ?
H331 C33 H332 107.0(14) . . ?
C33 C34 H341 110.4(12) . . ?
C33 C34 H342 110.7(12) . . ?
H341 C34 H342 107.7(17) . . ?
C33 C34 H343 109.9(13) . . ?
H341 C34 H343 108.9(17) . . ?
H342 C34 H343 109.2(18) . . ?
C42 C41 N3 115.27(9) . . ?
C42 C41 H411 110.9(8) . . ?
N3 C41 H411 105.9(8) . . ?
C42 C41 H412 111.7(8) . . ?
N3 C41 H412 105.8(8) . . ?
H411 C41 H412 106.7(12) . . ?
C41 C42 C43 110.92(11) . . ?
C41 C42 H421 110.5(10) . . ?
C43 C42 H421 109.8(10) . . ?
C41 C42 H422 111.0(9) . . ?
C43 C42 H422 108.9(10) . . ?
H421 C42 H422 105.6(14) . . ?
C44 C43 C42 111.42(12) . . ?
C44 C43 H431 111.3(11) . . ?
C42 C43 H431 107.9(11) . . ?
C44 C43 H432 110.4(10) . . ?
C42 C43 H432 109.4(10) . . ?
H431 C43 H432 106.3(15) . . ?
C43 C44 H441 109.5(13) . . ?
C43 C44 H442 112.7(12) . . ?
H441 C44 H442 109.4(17) . . ?
C43 C44 H443 108.9(11) . . ?
H441 C44 H443 107.2(17) . . ?
H442 C44 H443 109.0(16) . . ?
O1 C1 O2 125.58(16) . . ?
O1 C1 C10 117.45(14) . . ?
O2 C1 C10 116.97(14) . . ?
C1 C10 H103 109.5 . . ?
C1 C10 H102 109.5 . . ?
H103 C10 H102 109.5 . . ?
C1 C10 H101 109.5 . . ?
H103 C10 H101 109.5 . . ?
H102 C10 H101 109.5 . . ?
N2 N1 H11 105.1(15) . . ?
N2 N1 H12 106(3) . . ?
H11 N1 H12 102(3) . . ?
N1 N2 H21 108.9(14) . . ?
N1 N2 H22 102.9(19) . . ?
H21 N2 H22 104(2) . . ?
H1 O10 H2 120.5 . . ?

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
H11 N1 N2 H21 11(2) . . . . ?
H11 N1 N2 H22 -99(3) . . . . ?
H12 N1 N2 H21 -97(3) . . . . ?
H12 N1 N2 H22 153(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 H11 O1 0.873(16) 2.145(17) 2.979(3) 160(2) .
N2 H21 O2 0.811(16) 2.268(16) 3.072(2) 171.6(19) .
O10 H1 O1 0.80 2.28 3.081(9) 179.8 .

_refine_diff_density_max         0.502
_refine_diff_density_min         -0.216
_refine_diff_density_rms         0.037


_chemical_properties_physical    Moisture-sensitive,Hygroscopic
####################################################################### 
# 
# 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_z
_database_code_depnum_ccdc_archive 'CCDC 1922855'
loop_
_audit_author_name
_audit_author_address
'Andrei Churakov'
;Institute of General and Inorganic Chemistry RAS
Russia
;
_audit_update_record             
;
2019-08-14 deposited with the CCDC.	2019-08-28 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         'C16 H36 N, C2 H3 O2, H4 N2'
_chemical_formula_sum            'C18 H43 N3 O2'
_chemical_formula_weight         333.55

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           56
_space_group_name_H-M_alt        'P c c n'
_space_group_name_Hall           '-P 2ab 2ac'

_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+1/2, z'
'-x, y+1/2, -z+1/2'
'x+1/2, -y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z'
'x, -y-1/2, z-1/2'
'-x-1/2, y, z-1/2'

_cell_length_a                   16.8256(5)
_cell_length_b                   17.1025(5)
_cell_length_c                   15.0186(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4321.8(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    9971
_cell_measurement_theta_min      2.963
_cell_measurement_theta_max      30.496

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.025
_exptl_crystal_F_000             1504
_exptl_transmission_factor_min   0.8774
_exptl_transmission_factor_max   0.9705
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.500
_exptl_crystal_size_min          0.400
_exptl_absorpt_coefficient_mu    0.066
_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  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   'SADABS (Bruker, 2016)'
_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'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            70096
_diffrn_reflns_av_unetI/netI     0.0137
_diffrn_reflns_av_R_equivalents  0.0333
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.963
_diffrn_reflns_theta_max         26.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             4676
_reflns_number_gt                4028
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_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)+(0.0643P)²+1.1191P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refU
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4676
_refine_ls_number_parameters     372
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0521
_refine_ls_R_factor_gt           0.0447
_refine_ls_wR_factor_ref         0.1218
_refine_ls_wR_factor_gt          0.1163
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_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
N3 N 0.41506(5) 0.40837(5) 0.34830(5) 0.0224(2) Uani 1 1 d . . . . .
C11 C 0.32879(6) 0.38143(6) 0.35346(7) 0.0254(2) Uani 1 1 d . . . . .
C12 C 0.29142(7) 0.38588(9) 0.44483(8) 0.0363(3) Uani 1 1 d . . . . .
C13 C 0.20668(7) 0.35567(8) 0.44260(9) 0.0341(3) Uani 1 1 d . . . . .
C14 C 0.16460(9) 0.36619(14) 0.53066(11) 0.0639(5) Uani 1 1 d . . . . .
C21 C 0.42548(6) 0.48910(6) 0.38897(7) 0.0236(2) Uani 1 1 d . . . . .
C22 C 0.37716(7) 0.55345(7) 0.34630(8) 0.0308(3) Uani 1 1 d . . . . .
C23 C 0.38728(8) 0.62838(7) 0.39966(9) 0.0356(3) Uani 1 1 d . . . . .
C24 C 0.34695(11) 0.69779(9) 0.35743(15) 0.0588(5) Uani 1 1 d . . . . .
C31 C 0.43666(6) 0.40799(6) 0.25005(6) 0.0255(2) Uani 1 1 d . . . . .
C32 C 0.52229(7) 0.42926(8) 0.23033(7) 0.0314(3) Uani 1 1 d . . . . .
C33 C 0.54234(8) 0.41990(9) 0.13273(8) 0.0378(3) Uani 1 1 d . . . . .
C34 C 0.63005(9) 0.43441(11) 0.11529(10) 0.0494(4) Uani 1 1 d . . . . .
C41 C 0.46934(6) 0.35471(6) 0.40139(7) 0.0250(2) Uani 1 1 d . . . . .
C42 C 0.47677(7) 0.27230(7) 0.36559(8) 0.0310(3) Uani 1 1 d . . . . .
C43 C 0.53098(8) 0.22339(7) 0.42429(9) 0.0360(3) Uani 1 1 d . . . . .
C44 C 0.53385(10) 0.13905(8) 0.39345(10) 0.0463(3) Uani 1 1 d . . . . .
H111 H 0.3001(8) 0.4132(7) 0.3118(9) 0.027(3) Uiso 1 1 d . . . . .
H112 H 0.3288(7) 0.3274(8) 0.3300(8) 0.026(3) Uiso 1 1 d . . . . .
H121 H 0.3204(10) 0.3574(10) 0.4870(12) 0.058(5) Uiso 1 1 d . . . . .
H122 H 0.2920(10) 0.4407(10) 0.4654(11) 0.055(5) Uiso 1 1 d . . . . .
H131 H 0.1772(10) 0.3831(9) 0.3958(11) 0.048(4) Uiso 1 1 d . . . . .
H132 H 0.2047(11) 0.3025(12) 0.4201(13) 0.070(5) Uiso 1 1 d . . . . .
H141 H 0.152(2) 0.431(2) 0.538(2) 0.158(12) Uiso 1 1 d . . . . .
H142 H 0.1144(13) 0.3421(12) 0.5318(13) 0.075(6) Uiso 1 1 d . . . . .
H143 H 0.1946(14) 0.3510(13) 0.5792(17) 0.091(7) Uiso 1 1 d . . . . .
H211 H 0.4108(7) 0.4840(7) 0.4503(9) 0.023(3) Uiso 1 1 d . . . . .
H212 H 0.4809(7) 0.4997(7) 0.3853(8) 0.022(3) Uiso 1 1 d . . . . .
H221 H 0.3953(9) 0.5626(9) 0.2849(11) 0.044(4) Uiso 1 1 d . . . . .
H222 H 0.3226(10) 0.5410(9) 0.3421(10) 0.047(4) Uiso 1 1 d . . . . .
H231 H 0.4431(10) 0.6394(9) 0.4075(10) 0.047(4) Uiso 1 1 d . . . . .
H232 H 0.3683(10) 0.6199(9) 0.4596(12) 0.054(4) Uiso 1 1 d . . . . .
H241 H 0.2917(14) 0.6870(13) 0.3484(15) 0.087(7) Uiso 1 1 d . . . . .
H242 H 0.3682(16) 0.7098(15) 0.295(2) 0.114(9) Uiso 1 1 d . . . . .
H243 H 0.3515(11) 0.7446(13) 0.3931(13) 0.073(6) Uiso 1 1 d . . . . .
H311 H 0.4246(7) 0.3564(7) 0.2291(8) 0.023(3) Uiso 1 1 d . . . . .
H312 H 0.3995(8) 0.4430(7) 0.2218(8) 0.025(3) Uiso 1 1 d . . . . .
H321 H 0.5333(9) 0.4823(10) 0.2477(11) 0.045(4) Uiso 1 1 d . . . . .
H322 H 0.5574(9) 0.3959(9) 0.2638(11) 0.046(4) Uiso 1 1 d . . . . .
H331 H 0.5089(11) 0.4549(10) 0.0982(12) 0.056(5) Uiso 1 1 d . . . . .
H332 H 0.5294(9) 0.3672(10) 0.1142(10) 0.044(4) Uiso 1 1 d . . . . .
H341 H 0.6656(13) 0.3937(14) 0.1470(15) 0.087(7) Uiso 1 1 d . . . . .
H342 H 0.6415(13) 0.4303(13) 0.0549(16) 0.084(6) Uiso 1 1 d . . . . .
H343 H 0.6471(12) 0.4840(13) 0.1368(13) 0.075(6) Uiso 1 1 d . . . . .
H411 H 0.5199(8) 0.3807(7) 0.4038(8) 0.023(3) Uiso 1 1 d . . . . .
H412 H 0.4475(7) 0.3552(7) 0.4620(9) 0.028(3) Uiso 1 1 d . . . . .
H421 H 0.4997(9) 0.2737(9) 0.3050(11) 0.046(4) Uiso 1 1 d . . . . .
H422 H 0.4256(9) 0.2474(9) 0.3619(9) 0.044(4) Uiso 1 1 d . . . . .
H431 H 0.5126(9) 0.2261(9) 0.4863(11) 0.053(4) Uiso 1 1 d . . . . .
H432 H 0.5838(10) 0.2453(10) 0.4233(11) 0.052(4) Uiso 1 1 d . . . . .
H441 H 0.4788(12) 0.1148(12) 0.3966(13) 0.070(6) Uiso 1 1 d . . . . .
H442 H 0.5691(11) 0.1066(12) 0.4291(13) 0.070(5) Uiso 1 1 d . . . . .
H443 H 0.5525(11) 0.1381(11) 0.3329(14) 0.068(5) Uiso 1 1 d . . . . .
C1 C 0.19031(8) 0.51129(9) 0.14740(8) 0.0420(3) Uani 1 1 d . . . . .
C10 C 0.22980(10) 0.59004(12) 0.13516(12) 0.0662(5) Uani 1 1 d . . . . .
H101 H 0.190498 0.631626 0.143927 0.169(14) Uiso 1 1 calc R . . . .
H102 H 0.251755 0.593614 0.074855 0.153(11) Uiso 1 1 calc R . . . .
H103 H 0.272721 0.595894 0.178759 0.133(10) Uiso 1 1 calc R . . . .
O1 O 0.22227(7) 0.46456(7) 0.19999(8) 0.0660(4) Uani 1 1 d . . . . .
O2 O 0.12747(5) 0.49943(6) 0.10424(5) 0.0422(2) Uani 1 1 d . . . . .
N1 N 0.15669(9) 0.30018(11) 0.20083(10) 0.0589(4) Uani 1 1 d . . . . .
N2 N 0.08628(8) 0.32840(10) 0.15559(11) 0.0607(4) Uani 1 1 d . . . . .
H21 H 0.0952(10) 0.3792(11) 0.1397(11) 0.050(4) Uiso 1 1 d . . . . .
H11 H 0.1869(12) 0.3446(12) 0.2060(12) 0.063(5) Uiso 1 1 d . . . . .
H12 H 0.1811(13) 0.2730(13) 0.1562(15) 0.082(7) Uiso 1 1 d . . . . .
H22 H 0.0494(15) 0.3299(14) 0.2009(16) 0.094(7) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N3 C31 1.5198(12) . ?
N3 C21 1.5200(13) . ?
N3 C41 1.5205(13) . ?
N3 C11 1.5248(13) . ?
C11 C12 1.5115(16) . ?
C11 H111 0.959(13) . ?
C11 H112 0.989(13) . ?
C12 C13 1.5168(15) . ?
C12 H121 0.936(18) . ?
C12 H122 0.987(17) . ?
C13 C14 1.511(2) . ?
C13 H131 0.979(17) . ?
C13 H132 0.97(2) . ?
C14 H141 1.14(4) . ?
C14 H142 0.94(2) . ?
C14 H143 0.92(3) . ?
C21 C22 1.5108(15) . ?
C21 H211 0.958(13) . ?
C21 H212 0.952(12) . ?
C22 C23 1.5210(16) . ?
C22 H221 0.983(16) . ?
C22 H222 0.945(16) . ?
C23 C24 1.507(2) . ?
C23 H231 0.966(17) . ?
C23 H232 0.967(18) . ?
C24 H241 0.96(2) . ?
C24 H242 1.03(3) . ?
C24 H243 0.97(2) . ?
C31 C32 1.5152(15) . ?
C31 H311 0.959(13) . ?
C31 H312 0.963(13) . ?
C32 C33 1.5127(15) . ?
C32 H321 0.961(16) . ?
C32 H322 0.963(17) . ?
C33 C34 1.5192(19) . ?
C33 H331 0.972(18) . ?
C33 H332 0.969(16) . ?
C34 H341 1.03(2) . ?
C34 H342 0.93(2) . ?
C34 H343 0.95(2) . ?
C41 C42 1.5137(16) . ?
C41 H411 0.960(13) . ?
C41 H412 0.982(13) . ?
C42 C43 1.5194(16) . ?
C42 H421 0.989(16) . ?
C42 H422 0.963(16) . ?
C43 C44 1.5158(19) . ?
C43 H431 0.982(17) . ?
C43 H432 0.964(17) . ?
C44 H441 1.02(2) . ?
C44 H442 0.97(2) . ?
C44 H443 0.96(2) . ?
C1 O1 1.2458(17) . ?
C1 O2 1.2566(15) . ?
C1 C10 1.513(2) . ?
C10 H101 0.9800 . ?
C10 H102 0.9800 . ?
C10 H103 0.9800 . ?
N1 N2 1.4486(19) . ?
N1 H11 0.92(2) . ?
N1 H12 0.91(2) . ?
N2 H21 0.913(18) . ?
N2 H22 0.92(3) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C31 N3 C21 111.49(8) . . ?
C31 N3 C41 111.28(8) . . ?
C21 N3 C41 105.56(7) . . ?
C31 N3 C11 106.00(7) . . ?
C21 N3 C11 111.33(8) . . ?
C41 N3 C11 111.27(8) . . ?
C12 C11 N3 115.28(8) . . ?
C12 C11 H111 110.8(7) . . ?
N3 C11 H111 105.9(8) . . ?
C12 C11 H112 111.8(7) . . ?
N3 C11 H112 105.3(7) . . ?
H111 C11 H112 107.3(10) . . ?
C11 C12 C13 110.72(10) . . ?
C11 C12 H121 111.8(11) . . ?
C13 C12 H121 109.1(11) . . ?
C11 C12 H122 109.2(10) . . ?
C13 C12 H122 109.8(10) . . ?
H121 C12 H122 106.1(14) . . ?
C14 C13 C12 112.37(11) . . ?
C14 C13 H131 109.5(9) . . ?
C12 C13 H131 109.2(9) . . ?
C14 C13 H132 113.6(12) . . ?
C12 C13 H132 111.0(11) . . ?
H131 C13 H132 100.4(15) . . ?
C13 C14 H141 106.7(17) . . ?
C13 C14 H142 112.6(12) . . ?
H141 C14 H142 105(2) . . ?
C13 C14 H143 113.6(14) . . ?
H141 C14 H143 108(2) . . ?
H142 C14 H143 110.7(19) . . ?
C22 C21 N3 115.42(8) . . ?
C22 C21 H211 109.6(7) . . ?
N3 C21 H211 105.9(7) . . ?
C22 C21 H212 111.4(7) . . ?
N3 C21 H212 105.2(7) . . ?
H211 C21 H212 109.0(10) . . ?
C21 C22 C23 109.27(9) . . ?
C21 C22 H221 110.3(9) . . ?
C23 C22 H221 108.9(9) . . ?
C21 C22 H222 112.8(9) . . ?
C23 C22 H222 109.5(9) . . ?
H221 C22 H222 106.0(13) . . ?
C24 C23 C22 113.05(11) . . ?
C24 C23 H231 109.6(9) . . ?
C22 C23 H231 109.7(9) . . ?
C24 C23 H232 111.2(10) . . ?
C22 C23 H232 109.1(10) . . ?
H231 C23 H232 103.8(13) . . ?
C23 C24 H241 110.2(13) . . ?
C23 C24 H242 112.7(15) . . ?
H241 C24 H242 104(2) . . ?
C23 C24 H243 112.6(12) . . ?
H241 C24 H243 108.3(17) . . ?
H242 C24 H243 108.2(19) . . ?
C32 C31 N3 114.59(8) . . ?
C32 C31 H311 111.0(7) . . ?
N3 C31 H311 105.8(7) . . ?
C32 C31 H312 112.5(7) . . ?
N3 C31 H312 105.6(7) . . ?
H311 C31 H312 106.8(10) . . ?
C33 C32 C31 112.09(10) . . ?
C33 C32 H321 108.7(9) . . ?
C31 C32 H321 110.9(9) . . ?
C33 C32 H322 107.8(9) . . ?
C31 C32 H322 109.9(9) . . ?
H321 C32 H322 107.4(13) . . ?
C32 C33 C34 111.50(11) . . ?
C32 C33 H331 108.8(10) . . ?
C34 C33 H331 111.7(10) . . ?
C32 C33 H332 109.1(9) . . ?
C34 C33 H332 108.7(9) . . ?
H331 C33 H332 106.8(14) . . ?
C33 C34 H341 111.9(12) . . ?
C33 C34 H342 111.0(13) . . ?
H341 C34 H342 106.2(18) . . ?
C33 C34 H343 112.3(12) . . ?
H341 C34 H343 105.6(17) . . ?
H342 C34 H343 109.6(18) . . ?
C42 C41 N3 115.17(8) . . ?
C42 C41 H411 111.8(7) . . ?
N3 C41 H411 105.8(7) . . ?
C42 C41 H412 111.6(7) . . ?
N3 C41 H412 104.9(7) . . ?
H411 C41 H412 107.0(10) . . ?
C41 C42 C43 110.86(10) . . ?
C41 C42 H421 109.7(9) . . ?
C43 C42 H421 108.2(9) . . ?
C41 C42 H422 111.0(9) . . ?
C43 C42 H422 109.1(9) . . ?
H421 C42 H422 107.9(12) . . ?
C44 C43 C42 111.45(11) . . ?
C44 C43 H431 110.2(9) . . ?
C42 C43 H431 109.6(9) . . ?
C44 C43 H432 109.6(10) . . ?
C42 C43 H432 109.3(10) . . ?
H431 C43 H432 106.6(13) . . ?
C43 C44 H441 110.2(11) . . ?
C43 C44 H442 113.2(12) . . ?
H441 C44 H442 107.3(16) . . ?
C43 C44 H443 108.3(12) . . ?
H441 C44 H443 109.6(16) . . ?
H442 C44 H443 108.2(16) . . ?
O1 C1 O2 125.92(15) . . ?
O1 C1 C10 117.30(13) . . ?
O2 C1 C10 116.77(12) . . ?
C1 C10 H101 109.5 . . ?
C1 C10 H102 109.5 . . ?
H101 C10 H102 109.5 . . ?
C1 C10 H103 109.5 . . ?
H101 C10 H103 109.5 . . ?
H102 C10 H103 109.5 . . ?
N2 N1 H11 102.5(12) . . ?
N2 N1 H12 101.2(14) . . ?
H11 N1 H12 103.5(18) . . ?
N1 N2 H21 107.7(11) . . ?
N1 N2 H22 102.3(15) . . ?
H21 N2 H22 106.1(18) . . ?

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
H11 N1 N2 H21 7.0(17) . . . . ?
H11 N1 N2 H22 -105(2) . . . . ?
H12 N1 N2 H21 -99.8(18) . . . . ?
H12 N1 N2 H22 149(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 H11 O1 0.92(2) 2.14(2) 3.020(2) 160.9(17) .
N2 H21 O2 0.913(18) 2.193(19) 3.103(2) 175.1(15) .

_refine_diff_density_max         0.285
_refine_diff_density_min         -0.158
_refine_diff_density_rms         0.030


_chemical_properties_physical    Moisture-sensitive,Hygroscopic
