# Electronic Supplementary Material (ESI) for Materials Chemistry Frontiers.
# This journal is © the Partner Organisations 2018

####################################################################### 
# 
# 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_AM
_database_code_depnum_ccdc_archive 'CCDC 1842339'
_audit_update_record             
;
2018-05-09 deposited with the CCDC.
2018-12-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C3 H5 N O'
_chemical_formula_sum            'C3 H5 N O'
_chemical_formula_weight         71.08

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   8.268(2)
_cell_length_b                   5.757(2)
_cell_length_c                   9.170(2)
_cell_angle_alpha                90.00(3)
_cell_angle_beta                 112.07(3)
_cell_angle_gamma                90.00(3)
_cell_volume                     404.5(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    2502
_cell_measurement_theta_min      5.78
_cell_measurement_theta_max      68.15

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.167
_exptl_crystal_F_000             152
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.220
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.742
_shelx_estimated_absorpt_T_min   0.854
_shelx_estimated_absorpt_T_max   0.897
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 VENTURE CMOS photon 100'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            3525
_diffrn_reflns_av_unetI/netI     0.0160
_diffrn_reflns_av_R_equivalents  0.0205
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         9.308
_diffrn_reflns_theta_max         68.270
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             722
_reflns_number_gt                656
_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-2014/7 (Sheldrick, 2014)'
_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)+(0.0619P)²+0.0389P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         722
_refine_ls_number_parameters     46
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0354
_refine_ls_R_factor_gt           0.0321
_refine_ls_wR_factor_ref         0.0957
_refine_ls_wR_factor_gt          0.0917
_refine_ls_goodness_of_fit_ref   1.062
_refine_ls_restrained_S_all      1.062
_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 0.51934(10) 0.76484(13) 0.36897(7) 0.0455(3) Uani 1 1 d . . . . .
C1 C 0.7221(2) 0.3671(2) 0.37432(15) 0.0576(4) Uani 1 1 d . . . . .
H1A H 0.6149 0.3827 0.2869 0.069 Uiso 1 1 calc R U . . .
H1B H 0.7961 0.2382 0.3804 0.069 Uiso 1 1 calc R U . . .
N1 N 0.71472(12) 0.86549(17) 0.60652(9) 0.0426(3) Uani 1 1 d . . . . .
H1C H 0.6547 0.9900 0.6104 0.051 Uiso 1 1 calc R U . . .
H1D H 0.8131 0.8333 0.6851 0.051 Uiso 1 1 calc R U . . .
C3 C 0.65696(13) 0.72646(17) 0.48227(10) 0.0341(3) Uani 1 1 d . . . . .
C2 C 0.76777(15) 0.5230(2) 0.48640(12) 0.0428(3) Uani 1 1 d . . . . .
H2 H 0.8754 0.5049 0.5731 0.051 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 C3 1.2387(13) . ?
C1 C2 1.3088(18) . ?
C1 H1A 0.9500 . ?
C1 H1B 0.9500 . ?
N1 C3 1.3258(13) . ?
N1 H1C 0.8800 . ?
N1 H1D 0.8800 . ?
C3 C2 1.4788(16) . ?
C2 H2 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 C1 H1A 120.0 . . ?
C2 C1 H1B 120.0 . . ?
H1A C1 H1B 120.0 . . ?
C3 N1 H1C 120.0 . . ?
C3 N1 H1D 120.0 . . ?
H1C N1 H1D 120.0 . . ?
O1 C3 N1 122.26(10) . . ?
O1 C3 C2 121.85(10) . . ?
N1 C3 C2 115.88(9) . . ?
C1 C2 C3 122.00(11) . . ?
C1 C2 H2 119.0 . . ?
C3 C2 H2 119.0 . . ?

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
O1 C3 C2 C1 -3.39(17) . . . . ?
N1 C3 C2 C1 177.08(11) . . . . ?

_refine_diff_density_max         0.133
_refine_diff_density_min         -0.162
_refine_diff_density_rms         0.028



_chemical_properties_physical    Moisture-sensitive
_exptl_crystal_preparation       Luminescent
####################################################################### 
# 
# 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_NIPAM
_database_code_depnum_ccdc_archive 'CCDC 1842340'
_audit_update_record             
;
2018-05-09 deposited with the CCDC.
2018-12-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H11 N O'
_chemical_formula_sum            'C6 H11 N O'
_chemical_formula_weight         113.16

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   13.0023(5)
_cell_length_b                   12.2587(5)
_cell_length_c                   9.6452(3)
_cell_angle_alpha                90
_cell_angle_beta                 111.204(2)
_cell_angle_gamma                90
_cell_volume                     1433.28(9)
_cell_formula_units_Z            8
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    3739
_cell_measurement_theta_min      3.65
_cell_measurement_theta_max      68.39

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.049
_exptl_crystal_F_000             496
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.571
_shelx_estimated_absorpt_T_min   0.870
_shelx_estimated_absorpt_T_max   0.894
_exptl_absorpt_correction_type   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker D8 VENTURE CMOS photon 100'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            11716
_diffrn_reflns_av_unetI/netI     0.0583
_diffrn_reflns_av_R_equivalents  0.0774
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         3.646
_diffrn_reflns_theta_max         68.507
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             2629
_reflns_number_gt                1863
_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-2014/7 (Sheldrick, 2014)'
_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)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_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         2629
_refine_ls_number_parameters     153
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0810
_refine_ls_R_factor_gt           0.0527
_refine_ls_wR_factor_ref         0.1611
_refine_ls_wR_factor_gt          0.1399
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_restrained_S_all      1.008
_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 0.75624(12) 0.75742(14) 0.78125(13) 0.0413(4) Uani 1 1 d . . . . .
N1 N 0.81927(13) 0.72154(14) 0.59709(15) 0.0312(4) Uani 1 1 d . . . . .
H1 H 0.8017 0.7160 0.5003 0.037 Uiso 1 1 calc R U . . .
C1 C 0.54558(19) 0.7978(2) 0.5631(2) 0.0530(7) Uani 1 1 d . . . . .
H1A H 0.5506 0.7983 0.6638 0.064 Uiso 1 1 calc R U . . .
H1B H 0.4772 0.8131 0.4858 0.064 Uiso 1 1 calc R U . . .
O2 O 0.28404(12) 0.78486(12) 0.31309(13) 0.0365(4) Uani 1 1 d . . . . .
N2 N 0.27007(14) 0.68988(14) 0.10664(15) 0.0322(4) Uani 1 1 d . . . . .
H2 H 0.2676 0.6939 0.0144 0.039 Uiso 1 1 calc R U . . .
C2 C 0.63227(17) 0.77622(17) 0.53105(19) 0.0339(5) Uani 1 1 d . . . . .
C3 C 0.74158(15) 0.75162(16) 0.64767(18) 0.0277(4) Uani 1 1 d . . . . .
H3 H 0.6319(19) 0.7787(19) 0.428(3) 0.045(6) Uiso 1 1 d . . . . .
C6 C 0.9774(3) 0.6071(3) 0.6249(3) 0.0727(9) Uani 1 1 d . . . . .
H6A H 0.9300 0.5427 0.6100 0.109 Uiso 1 1 calc R U . . .
H6B H 1.0523 0.5886 0.6912 0.109 Uiso 1 1 calc R U . . .
H6C H 0.9788 0.6315 0.5288 0.109 Uiso 1 1 calc R U . . .
C5 C 1.0029(2) 0.7981(3) 0.7205(4) 0.0670(8) Uani 1 1 d . . . . .
H5A H 1.0094 0.8220 0.6271 0.100 Uiso 1 1 calc R U . . .
H5B H 1.0764 0.7822 0.7935 0.100 Uiso 1 1 calc R U . . .
H5C H 0.9685 0.8560 0.7588 0.100 Uiso 1 1 calc R U . . .
C4 C 0.93284(16) 0.69697(18) 0.69322(19) 0.0357(5) Uani 1 1 d . . . . .
H4 H 0.9322 0.6706 0.7910 0.043 Uiso 1 1 calc R U . . .
C8 C 0.30013(18) 0.88119(18) 0.1075(2) 0.0382(5) Uani 1 1 d . . . . .
H8 H 0.2997 0.8743 0.0092 0.046 Uiso 1 1 calc R U . . .
C7 C 0.3149(2) 0.9775(2) 0.1691(3) 0.0539(7) Uani 1 1 d . . . . .
H7A H 0.3155 0.9860 0.2674 0.065 Uiso 1 1 calc R U . . .
H7B H 0.3250 1.0392 0.1158 0.065 Uiso 1 1 calc R U . . .
C9 C 0.28397(15) 0.78232(16) 0.18528(18) 0.0280(4) Uani 1 1 d . . . . .
C11 C 0.3713(2) 0.5319(2) 0.2462(3) 0.0519(6) Uani 1 1 d . . . . .
H11A H 0.4098 0.5227 0.1764 0.078 Uiso 1 1 calc R U . . .
H11B H 0.3620 0.4606 0.2861 0.078 Uiso 1 1 calc R U . . .
H11C H 0.4147 0.5796 0.3280 0.078 Uiso 1 1 calc R U . . .
C10 C 0.25879(17) 0.58269(17) 0.16584(19) 0.0336(5) Uani 1 1 d . . . . .
H10 H 0.2215 0.5925 0.2393 0.040 Uiso 1 1 calc R U . . .
C12 C 0.1860(2) 0.51112(19) 0.0406(2) 0.0475(6) Uani 1 1 d . . . . .
H12A H 0.1131 0.5450 -0.0046 0.071 Uiso 1 1 calc R U . . .
H12B H 0.1781 0.4393 0.0801 0.071 Uiso 1 1 calc R U . . .
H12C H 0.2196 0.5028 -0.0348 0.071 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 C3 1.234(2) . ?
N1 C3 1.323(3) . ?
N1 C4 1.463(2) . ?
N1 H1 0.8800 . ?
C1 C2 1.299(3) . ?
C1 H1A 0.9500 . ?
C1 H1B 0.9500 . ?
O2 C9 1.233(2) . ?
N2 C9 1.339(3) . ?
N2 C10 1.461(3) . ?
N2 H2 0.8800 . ?
C2 C3 1.490(3) . ?
C2 H3 0.99(2) . ?
C6 C4 1.503(3) . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C5 C4 1.504(4) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C4 H4 1.0000 . ?
C8 C7 1.305(3) . ?
C8 C9 1.480(3) . ?
C8 H8 0.9500 . ?
C7 H7A 0.9500 . ?
C7 H7B 0.9500 . ?
C11 C10 1.519(3) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C10 C12 1.516(3) . ?
C10 H10 1.0000 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 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
C3 N1 C4 123.63(15) . . ?
C3 N1 H1 118.2 . . ?
C4 N1 H1 118.2 . . ?
C2 C1 H1A 120.0 . . ?
C2 C1 H1B 120.0 . . ?
H1A C1 H1B 120.0 . . ?
C9 N2 C10 123.49(15) . . ?
C9 N2 H2 118.3 . . ?
C10 N2 H2 118.3 . . ?
C1 C2 C3 122.31(18) . . ?
C1 C2 H3 122.8(14) . . ?
C3 C2 H3 114.8(14) . . ?
O1 C3 N1 123.41(17) . . ?
O1 C3 C2 121.42(18) . . ?
N1 C3 C2 115.16(15) . . ?
C4 C6 H6A 109.5 . . ?
C4 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C4 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C4 C5 H5A 109.5 . . ?
C4 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C4 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
N1 C4 C6 109.48(17) . . ?
N1 C4 C5 110.46(19) . . ?
C6 C4 C5 112.1(2) . . ?
N1 C4 H4 108.2 . . ?
C6 C4 H4 108.2 . . ?
C5 C4 H4 108.2 . . ?
C7 C8 C9 122.34(19) . . ?
C7 C8 H8 118.8 . . ?
C9 C8 H8 118.8 . . ?
C8 C7 H7A 120.0 . . ?
C8 C7 H7B 120.0 . . ?
H7A C7 H7B 120.0 . . ?
O2 C9 N2 122.61(18) . . ?
O2 C9 C8 122.50(18) . . ?
N2 C9 C8 114.89(16) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N2 C10 C12 109.33(15) . . ?
N2 C10 C11 110.71(18) . . ?
C12 C10 C11 112.2(2) . . ?
N2 C10 H10 108.2 . . ?
C12 C10 H10 108.2 . . ?
C11 C10 H10 108.2 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 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 N1 C3 O1 -3.2(3) . . . . ?
C4 N1 C3 C2 178.15(18) . . . . ?
C1 C2 C3 O1 -4.6(3) . . . . ?
C1 C2 C3 N1 174.1(2) . . . . ?
C3 N1 C4 C6 145.6(2) . . . . ?
C3 N1 C4 C5 -90.5(3) . . . . ?
C10 N2 C9 O2 -2.9(3) . . . . ?
C10 N2 C9 C8 176.61(17) . . . . ?
C7 C8 C9 O2 -0.4(3) . . . . ?
C7 C8 C9 N2 -179.9(2) . . . . ?
C9 N2 C10 C12 149.2(2) . . . . ?
C9 N2 C10 C11 -86.7(2) . . . . ?

_refine_diff_density_max         0.191
_refine_diff_density_min         -0.290
_refine_diff_density_rms         0.047



