# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_I
_database_code_depnum_ccdc_archive 'CCDC 2023499'
loop_
_audit_author_name
_audit_author_address
'Young Jun Park'
;Ewha Womans University
South Korea
;
_audit_update_record             
;
2020-08-16 deposited with the CCDC.	2020-10-08 downloaded from the CCDC.
;
_chemical_name_systematic        'methyl ammonium methyl carbamate'
_chemical_name_common            'methyl ammonium methyl carbamate'
_chemical_formula_moiety         CH3NH3+CH3NHCO2-
_chemical_formula_sum            'C3 H10 N2 O2'
_chemical_formula_iupac          ?
_chemical_formula_weight         106.13
_chemical_absolute_configuration ?

_chemical_melting_point          ?

_space_group_crystal_system      orthorhombic
_space_group_name_H-M_alt        'P n a 21'
_space_group_name_Hall           'P 2c -2n'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'

_cell_length_a                   9.3493(2)
_cell_length_b                   6.97870(10)
_cell_length_c                   9.1550(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     597.33(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9452
_cell_measurement_theta_min      2.2246
_cell_measurement_theta_max      28.2852
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       block
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_size_max          0.500
_exptl_crystal_size_mid          0.500
_exptl_crystal_size_min          0.500
_exptl_crystal_density_diffrn    1.180
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             232

_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.91
_exptl_absorpt_correction_T_max  0.95

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   ?
_diffrn_source_type              ?

_diffrn_radiation_type           ?
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  ?

_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            9455
_diffrn_reflns_av_R_equivalents  0.0270
_diffrn_reflns_av_sigmaI/netI    0.0109
_diffrn_reflns_theta_min         3.64
_diffrn_reflns_theta_max         28.29
_diffrn_reflns_theta_full        28.29
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       12

_refine_special_details          
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_reflns_number_total             1444
_reflns_number_gt                1436
_reflns_threshold_expression     >2sigma(I)

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0243
_refine_ls_R_factor_gt           0.0243
_refine_ls_wR_factor_gt          0.0588
_refine_ls_wR_factor_ref         0.0589
_refine_ls_goodness_of_fit_ref   1.190
_refine_ls_restrained_S_all      1.189
_refine_ls_number_reflns         1444
_refine_ls_number_parameters     104
_refine_ls_number_restraints     1
_refine_ls_hydrogen_treatment    mixed
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0435P)²+0.0130P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.308
_refine_diff_density_min         -0.231
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.2(6)

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'

_computing_data_collection       ?
_computing_cell_refinement       'SAINT V8.27B (Bruker AXS Inc., 2012)'
_computing_data_reduction        'SAINT V8.27B (Bruker AXS Inc., 2012)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N N1 0.03714(6) 0.79906(8) 0.88022(6) 0.01573(13) Uani d . 1 . .
N N2 0.28154(6) 0.25393(10) 0.76651(7) 0.01919(14) Uani d . 1 . .
C C3 0.25999(9) 0.22953(11) 0.92245(8) 0.02376(16) Uani d . 1 . .
C C2 0.18513(6) 0.19429(8) 0.66511(8) 0.01441(13) Uani d . 1 . .
C C1 0.02591(9) 0.63898(12) 0.77505(9) 0.02575(17) Uani d . 1 . .
O O2 0.21558(5) 0.22271(7) 0.53068(5) 0.01812(13) Uani d . 1 . .
O O1 0.06933(5) 0.11650(7) 0.70663(6) 0.01929(12) Uani d . 1 . .
H H10 0.3588(13) 0.2956(13) 0.7365(14) 0.021(2) Uiso d . 1 . .
H H2 0.1174(16) 0.629(2) 0.7233(19) 0.050(4) Uiso d . 1 . .
H H3 -0.0486(16) 0.664(3) 0.711(2) 0.050(4) Uiso d . 1 . .
H H1 0.0106(14) 0.526(2) 0.8291(15) 0.037(3) Uiso d . 1 . .
H H9 0.2798(11) 0.1026(18) 0.9527(14) 0.029(3) Uiso d . 1 . .
H H8 0.3121(17) 0.312(3) 0.975(2) 0.050(4) Uiso d . 1 . .
H H4 0.0506(12) 0.9123(18) 0.8320(15) 0.025(3) Uiso d . 1 . .
H H5 -0.0446(12) 0.8061(16) 0.9339(14) 0.019(2) Uiso d . 1 . .
H H6 0.1075(13) 0.7795(13) 0.9362(14) 0.021(2) Uiso d . 1 . .
H H7 0.1602(18) 0.259(2) 0.946(2) 0.046(4) Uiso d . 1 . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
N1 0.0135(2) 0.0195(3) 0.0142(3) -0.00013(18) 0.0001(2) 0.0031(2)
N2 0.0161(3) 0.0258(3) 0.0157(3) -0.0028(2) -0.0007(2) 0.0009(2)
C3 0.0288(4) 0.0279(4) 0.0146(3) 0.0002(3) -0.0026(3) 0.0002(3)
C2 0.0126(2) 0.0132(2) 0.0174(3) 0.00253(19) 0.0001(2) 0.0025(2)
C1 0.0312(4) 0.0255(4) 0.0206(3) -0.0005(3) 0.0005(3) -0.0031(3)
O2 0.0136(2) 0.0250(2) 0.0157(3) -0.00245(16) -0.00036(17) 0.00256(19)
O1 0.0128(2) 0.0229(2) 0.0222(2) -0.00081(15) 0.00042(18) 0.00811(18)

_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N1 C1 . 1.4786(10) ?
N2 C2 . 1.3592(9) ?
N2 C3 . 1.4517(10) ?
C2 O1 . 1.2694(7) ?
C2 O2 . 1.2787(9) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 N2 C3 . . 122.93(6) ?
O1 C2 O2 . . 122.98(6) ?
O1 C2 N2 . . 119.48(7) ?
O2 C2 N2 . . 117.53(6) ?

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Methanol'
_chemical_properties_physical    Heat-sensitive
####################################################################### 
# 
# 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_I_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2023500'
loop_
_audit_author_name
_audit_author_address
'Young Jun Park'
;Ewha Womans University
South Korea
;
_audit_update_record             
;
2020-08-16 deposited with the CCDC.	2020-10-08 downloaded from the CCDC.
;
_chemical_name_systematic        '3-nitrobenzylidene methanamine'
_chemical_name_common            '3-nitrobenzylidene methanamine'
_chemical_formula_moiety         ?
_chemical_formula_sum            'C8 H8 N2 O2'
_chemical_formula_iupac          ?
_chemical_formula_weight         164.16

_chemical_melting_point          ?

_space_group_crystal_system      monoclinic
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   7.4527(2)
_cell_length_b                   18.3181(4)
_cell_length_c                   11.3999(2)
_cell_angle_alpha                90
_cell_angle_beta                 90.8690(10)
_cell_angle_gamma                90
_cell_volume                     1556.13(6)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    9879
_cell_measurement_theta_min      2.2236
_cell_measurement_theta_max      28.2821
_cell_measurement_temperature    100.(2)

_exptl_crystal_description       'thin plate'
_exptl_crystal_colour            ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.020
_exptl_crystal_density_diffrn    1.401
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             688

_exptl_absorpt_coefficient_mu    0.103
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2012/1 (Bruker AXS Inc.)'
_exptl_absorpt_correction_T_min  0.94
_exptl_absorpt_correction_T_max  1.00

_exptl_special_details           
;
;

_diffrn_ambient_temperature      100.(2)

_diffrn_source                   ?
_diffrn_source_type              ?

_diffrn_radiation_type           ?
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  ?

_diffrn_measurement_device_type  ?
_diffrn_measurement_method       ?

_diffrn_detector_area_resol_mean 8.3333

_diffrn_reflns_number            25197
_diffrn_reflns_av_R_equivalents  0.0220
_diffrn_reflns_av_sigmaI/netI    0.0180
_diffrn_reflns_theta_min         2.10
_diffrn_reflns_theta_max         28.34
_diffrn_reflns_theta_full        28.34
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       15

_refine_special_details          
;
Refinement of F² against ALL reflections.  The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement.  R-factors based
on F² are statistically about twice as large as those based on F, and R-
factors based on ALL data will be even larger.
;

_reflns_number_total             3852
_reflns_number_gt                3091
_reflns_threshold_expression     >2sigma(I)

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_R_factor_all          0.0518
_refine_ls_R_factor_gt           0.0379
_refine_ls_wR_factor_gt          0.0979
_refine_ls_wR_factor_ref         0.1055
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_restrained_S_all      1.014
_refine_ls_number_reflns         3852
_refine_ls_number_parameters     219
_refine_ls_number_restraints     0
_refine_ls_hydrogen_treatment    constr
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0575P)²+0.4255P] where P=(Fo²+2Fc²)/3'

_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap

_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.455
_refine_diff_density_min         -0.194
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables 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'

_computing_data_collection       ?
_computing_cell_refinement       'SAINT V8.27B (Bruker AXS Inc., 2012)'
_computing_data_reduction        'SAINT V8.27B (Bruker AXS Inc., 2012)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N N2 0.13675(12) 0.39144(5) 0.89339(8) 0.0163(2) Uani d . 1 . .
N N3 0.45972(12) 0.90647(5) 0.69923(8) 0.0173(2) Uani d . 1 . .
N N1 0.07660(12) 0.11349(5) 0.85873(9) 0.0183(2) Uani d . 1 . .
N N4 0.32867(12) 0.64353(5) 0.55512(8) 0.0160(2) Uani d . 1 . .
O O3 0.40143(11) 0.63698(5) 0.65181(7) 0.0228(2) Uani d . 1 . .
O O2 0.07189(11) 0.38031(4) 0.79544(7) 0.0218(2) Uani d . 1 . .
O O1 0.15384(12) 0.45293(4) 0.93622(8) 0.0265(2) Uani d . 1 . .
O O4 0.29046(12) 0.59161(5) 0.49136(8) 0.0262(2) Uani d . 1 . .
C C4 0.30195(14) 0.21103(6) 1.09699(10) 0.0166(2) Uani d . 1 . .
H H4A 0.3402 0.1704 1.1428 0.02 Uiso calc R 1 . .
C C8 0.16445(13) 0.25948(6) 0.92058(9) 0.0130(2) Uani d . 1 . .
H H8 0.1084 0.2528 0.846 0.016 Uiso calc R 1 . .
C C15 0.28666(14) 0.71762(6) 0.51240(9) 0.0138(2) Uani d . 1 . .
C C11 0.30244(13) 0.84655(6) 0.54077(10) 0.0140(2) Uani d . 1 . .
C C12 0.21793(14) 0.85582(6) 0.43150(10) 0.0165(2) Uani d . 1 . .
H H12 0.1937 0.9037 0.4033 0.02 Uiso calc R 1 . .
C C2 0.17679(14) 0.12482(6) 0.94701(10) 0.0160(2) Uani d . 1 . .
H H2A 0.2278 0.0844 0.9875 0.019 Uiso calc R 1 . .
C C3 0.21672(13) 0.19939(6) 0.98890(9) 0.0141(2) Uani d . 1 . .
C C7 0.19623(13) 0.32874(6) 0.96406(9) 0.0139(2) Uani d . 1 . .
C C6 0.27809(14) 0.34126(6) 1.07229(10) 0.0171(2) Uani d . 1 . .
H H6 0.2969 0.3896 1.1002 0.02 Uiso calc R 1 . .
C C16 0.33604(13) 0.77610(6) 0.58242(9) 0.0131(2) Uani d . 1 . .
H H16 0.3915 0.7685 0.657 0.016 Uiso calc R 1 . .
C C14 0.20372(14) 0.72559(6) 0.40309(10) 0.0165(2) Uani d . 1 . .
H H14 0.172 0.6842 0.357 0.02 Uiso calc R 1 . .
C C10 0.35972(14) 0.91109(6) 0.60906(10) 0.0165(2) Uani d . 1 . .
H H10 0.3199 0.9579 0.5843 0.02 Uiso calc R 1 . .
C C13 0.16883(14) 0.79572(6) 0.36345(10) 0.0175(2) Uani d . 1 . .
H H13 0.1111 0.8029 0.2895 0.021 Uiso calc R 1 . .
C C5 0.33161(14) 0.28165(7) 1.13842(10) 0.0179(2) Uani d . 1 . .
H H5 0.3889 0.2889 1.2125 0.022 Uiso calc R 1 . .
C C1 0.04069(16) 0.03813(6) 0.82499(12) 0.0234(3) Uani d . 1 . .
H H1A 0.1102 0.0052 0.876 0.035 Uiso calc R 1 . .
H H1B 0.0753 0.0307 0.7433 0.035 Uiso calc R 1 . .
H H1C -0.0876 0.0278 0.833 0.035 Uiso calc R 1 . .
C C9 0.51010(15) 0.97431(6) 0.75785(11) 0.0205(2) Uani d . 1 . .
H H9A 0.4557 1.0156 0.7159 0.031 Uiso calc R 1 . .
H H9B 0.641 0.9794 0.7583 0.031 Uiso calc R 1 . .
H H9C 0.4675 0.9735 0.8387 0.031 Uiso calc R 1 . .

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
N2 0.0157(4) 0.0138(5) 0.0196(5) -0.0002(3) 0.0020(4) 0.0000(4)
N3 0.0165(4) 0.0139(5) 0.0215(5) -0.0009(4) -0.0007(4) -0.0024(4)
N1 0.0166(5) 0.0135(5) 0.0247(5) -0.0009(3) -0.0027(4) -0.0006(4)
N4 0.0150(4) 0.0144(5) 0.0186(5) -0.0007(3) 0.0024(4) -0.0015(4)
O3 0.0278(4) 0.0174(4) 0.0228(4) 0.0015(3) -0.0074(3) 0.0015(3)
O2 0.0258(4) 0.0189(4) 0.0205(4) 0.0011(3) -0.0046(3) 0.0019(3)
O1 0.0355(5) 0.0132(4) 0.0308(5) 0.0005(3) 0.0000(4) -0.0049(3)
O4 0.0369(5) 0.0153(4) 0.0264(5) -0.0030(4) -0.0003(4) -0.0075(3)
C4 0.0113(5) 0.0224(6) 0.0163(5) 0.0003(4) 0.0005(4) 0.0041(4)
C8 0.0104(5) 0.0150(5) 0.0135(5) -0.0006(4) 0.0005(4) -0.0004(4)
C15 0.0106(5) 0.0140(5) 0.0168(5) 0.0001(4) 0.0023(4) 0.0007(4)
C11 0.0097(5) 0.0152(5) 0.0170(5) 0.0005(4) 0.0016(4) 0.0007(4)
C12 0.0123(5) 0.0182(6) 0.0189(6) 0.0012(4) 0.0010(4) 0.0043(4)
C2 0.0137(5) 0.0147(5) 0.0195(6) 0.0013(4) -0.0006(4) 0.0042(4)
C3 0.0097(5) 0.0158(5) 0.0169(5) -0.0009(4) 0.0017(4) 0.0011(4)
C7 0.0112(5) 0.0142(5) 0.0163(5) 0.0002(4) 0.0022(4) 0.0007(4)
C6 0.0141(5) 0.0195(6) 0.0177(5) -0.0033(4) 0.0029(4) -0.0050(4)
C16 0.0103(5) 0.0154(5) 0.0137(5) 0.0001(4) 0.0004(4) 0.0005(4)
C14 0.0117(5) 0.0217(6) 0.0160(5) -0.0030(4) 0.0013(4) -0.0037(4)
C10 0.0157(5) 0.0136(5) 0.0203(6) 0.0010(4) 0.0003(4) 0.0015(4)
C13 0.0117(5) 0.0268(6) 0.0139(5) -0.0006(4) -0.0015(4) 0.0022(4)
C5 0.0122(5) 0.0280(6) 0.0136(5) -0.0020(4) -0.0006(4) -0.0016(4)
C1 0.0213(6) 0.0156(6) 0.0331(7) -0.0009(4) -0.0046(5) -0.0028(5)
C9 0.0209(6) 0.0159(6) 0.0245(6) -0.0019(4) -0.0021(5) -0.0040(4)

_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_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
N2 O2 . 1.2271(12) ?
N2 O1 . 1.2335(12) ?
N2 C7 . 1.4676(14) ?
N3 C10 . 1.2633(14) ?
N3 C9 . 1.4575(14) ?
N1 C2 . 1.2612(15) ?
N1 C1 . 1.4567(15) ?
N4 O3 . 1.2268(12) ?
N4 O4 . 1.2279(12) ?
N4 C15 . 1.4740(14) ?
C4 C5 . 1.3936(16) ?
C4 C3 . 1.3940(15) ?
C8 C7 . 1.3812(15) ?
C8 C3 . 1.4003(14) ?
C15 C16 . 1.3825(15) ?
C15 C14 . 1.3902(15) ?
C11 C16 . 1.3963(15) ?
C11 C12 . 1.3976(15) ?
C11 C10 . 1.4751(15) ?
C12 C13 . 1.3925(16) ?
C2 C3 . 1.4759(15) ?
C7 C6 . 1.3871(15) ?
C6 C5 . 1.3824(16) ?
C14 C13 . 1.3852(16) ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O2 N2 O1 . . 123.29(10) ?
O2 N2 C7 . . 118.75(9) ?
O1 N2 C7 . . 117.96(9) ?
C10 N3 C9 . . 117.43(10) ?
C2 N1 C1 . . 118.09(10) ?
O3 N4 O4 . . 123.47(9) ?
O3 N4 C15 . . 118.40(9) ?
O4 N4 C15 . . 118.13(9) ?
C5 C4 C3 . . 120.62(10) ?
C7 C8 C3 . . 118.53(10) ?
C16 C15 C14 . . 123.16(10) ?
C16 C15 N4 . . 117.99(9) ?
C14 C15 N4 . . 118.83(9) ?
C16 C11 C12 . . 119.44(10) ?
C16 C11 C10 . . 120.81(10) ?
C12 C11 C10 . . 119.72(10) ?
C13 C12 C11 . . 120.76(10) ?
N1 C2 C3 . . 121.64(10) ?
C4 C3 C8 . . 119.38(10) ?
C4 C3 C2 . . 120.96(10) ?
C8 C3 C2 . . 119.64(10) ?
C8 C7 C6 . . 122.80(10) ?
C8 C7 N2 . . 118.24(9) ?
C6 C7 N2 . . 118.94(10) ?
C5 C6 C7 . . 118.28(10) ?
C15 C16 C11 . . 118.36(10) ?
C13 C14 C15 . . 117.94(10) ?
N3 C10 C11 . . 122.56(10) ?
C14 C13 C12 . . 120.34(10) ?
C6 C5 C4 . . 120.36(10) ?

_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Pentane'
