# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 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_Compound-15
_database_code_depnum_ccdc_archive 'CCDC 1841089'
_audit_update_record             
;
2018-05-02 deposited with the CCDC.
2018-06-07 downloaded from the CCDC.
;

#=====================================================================
# start Validation Reply Form

_vrf_STRVA01_Compound-15         
;
RESPONSE: 
ADDSYM in PLATON was run and no addtional symmetry 
was found, which proves the space group P2(1)2(1)2(1) 
is correct. The strucutre was refined as an inversion twin (mix of enantiomers) 
so flack parameter is meaningless.
;

_vrf_PLAT032_Compound-15         
;
RESPONSE: 
ADDSYM in PLATON was run and no addtional symmetry 
was found, which proves the space group P2(1)2(1)2(1) 
is correct. The strucutre was refined as an inversion twin (mix of enantiomers) 
so flack parameter is meaningless.
;

# end Validation Reply Form 
#=====================================================================


_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C12 H14 N2 O'
_chemical_formula_sum            'C12 H14 N2 O'
_chemical_formula_weight         202.25

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   5.7386(4)
_cell_length_b                   9.5416(7)
_cell_length_c                   18.3137(13)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1002.77(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6214
_cell_measurement_theta_min      3.08
_cell_measurement_theta_max      30.43

_exptl_crystal_description       rod
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.340
_exptl_crystal_F_000             432
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.090
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.087
_shelx_estimated_absorpt_T_min   0.976
_shelx_estimated_absorpt_T_max   0.993
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9011
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker, 2016/2) was 
used for absorption correction. 
Krause, L., Herbst-Irmer, R.,
Sheldrick G.M. & Stalke D.,
J. Appl. Cryst. 48 (2015) 3-10.
;
_exptl_absorpt_special_details   ?


_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker D8 Venture PHOTON 100 CMOS'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12225
_diffrn_reflns_av_unetI/netI     0.0416
_diffrn_reflns_av_R_equivalents  0.0380
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         3.083
_diffrn_reflns_theta_max         30.490
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             3055
_reflns_number_gt                2647
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.712
_reflns_Friedel_fraction_max     0.997
_reflns_Friedel_fraction_full    0.996

_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_data_collection       'APEX3 v.2017.3-0 (Bruker AXS Inc., 2017)'
_computing_cell_refinement       'SAINT V.8.38A (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V.8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Xshell v.6.3.1 (Bruker AXS Inc., 2016)'
_computing_publication_material  'APEX3 v.2017.3-0 (Bruker AXS Inc., 2017)'

_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0414P)²+0.2174P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.4(19)
_chemical_absolute_configuration .
_refine_ls_number_reflns         3055
_refine_ls_number_parameters     147
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0572
_refine_ls_R_factor_gt           0.0449
_refine_ls_wR_factor_ref         0.0960
_refine_ls_wR_factor_gt          0.0903
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_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
C1 C 0.5536(3) 0.4324(2) 0.60372(10) 0.0184(4) Uani 1 1 d . . . . .
C2 C 0.5404(4) 0.5311(2) 0.54805(11) 0.0208(4) Uani 1 1 d . . . . .
H2 H 0.642675 0.527373 0.507318 0.025 Uiso 1 1 calc R U . . .
C3 C 0.3719(4) 0.6359(2) 0.55399(11) 0.0229(4) Uani 1 1 d . . . . .
H3 H 0.360561 0.704945 0.516796 0.028 Uiso 1 1 calc R U . . .
C4 C 0.2203(4) 0.6415(2) 0.61303(11) 0.0235(4) Uani 1 1 d . . . . .
H4 H 0.105587 0.713129 0.615555 0.028 Uiso 1 1 calc R U . . .
C5 C 0.2365(3) 0.54164(19) 0.66885(11) 0.0197(4) Uani 1 1 d . . . . .
H5 H 0.132497 0.544249 0.709192 0.024 Uiso 1 1 calc R U . . .
C6 C 0.4057(3) 0.43951(19) 0.66428(10) 0.0163(4) Uani 1 1 d . . . . .
C7 C 0.4704(3) 0.3242(2) 0.71748(10) 0.0168(4) Uani 1 1 d . . . . .
H7 H 0.555(4) 0.365(2) 0.7608(12) 0.021(5) Uiso 1 1 d . . . . .
C8 C 0.2703(3) 0.2290(2) 0.74086(10) 0.0178(4) Uani 1 1 d . . . . .
H8A H 0.292604 0.195854 0.791617 0.021 Uiso 1 1 calc R U . . .
H8B H 0.119221 0.278679 0.737539 0.021 Uiso 1 1 calc R U . . .
C9 C 0.2791(3) 0.10769(19) 0.68766(10) 0.0160(4) Uani 1 1 d . . . . .
C10 C 0.6335(3) 0.23157(19) 0.67055(10) 0.0161(3) Uani 1 1 d . . . . .
H10 H 0.775(4) 0.196(2) 0.6950(11) 0.015(5) Uiso 1 1 d . . . . .
C11 C 0.5680(3) -0.0005(2) 0.60526(10) 0.0188(4) Uani 1 1 d . . . . .
H11A H 0.456138 -0.078056 0.606129 0.028 Uiso 1 1 calc R U . . .
H11B H 0.718741 -0.032997 0.623844 0.028 Uiso 1 1 calc R U . . .
H11C H 0.586601 0.033086 0.555024 0.028 Uiso 1 1 calc R U . . .
C12 C 0.8912(3) 0.2888(2) 0.56084(10) 0.0190(4) Uani 1 1 d . . . . .
H12A H 0.830715 0.274170 0.511382 0.029 Uiso 1 1 calc R U . . .
H12B H 0.972508 0.204143 0.577191 0.029 Uiso 1 1 calc R U . . .
H12C H 0.999884 0.368035 0.560722 0.029 Uiso 1 1 calc R U . . .
N1 N 0.7006(3) 0.31843(18) 0.60970(10) 0.0253(4) Uani 1 1 d . . . . .
N2 N 0.4830(3) 0.11280(16) 0.65082(8) 0.0156(3) Uani 1 1 d . . . . .
O1 O 0.1299(2) 0.01636(14) 0.68048(8) 0.0228(3) Uani 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
C1 N1 1.380(2) . ?
C1 C2 1.390(3) . ?
C1 C6 1.398(3) . ?
C2 C3 1.395(3) . ?
C2 H2 0.9500 . ?
C3 C4 1.389(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.401(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.378(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.515(3) . ?
C7 C8 1.526(3) . ?
C7 C10 1.548(3) . ?
C7 H7 1.01(2) . ?
C8 C9 1.514(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 O1 1.229(2) . ?
C9 N2 1.351(2) . ?
C10 N1 1.441(2) . ?
C10 N2 1.470(2) . ?
C10 H10 0.99(2) . ?
C11 N2 1.450(2) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 N1 1.441(2) . ?
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
N1 C1 C2 128.72(18) . . ?
N1 C1 C6 110.27(16) . . ?
C2 C1 C6 121.01(17) . . ?
C1 C2 C3 117.81(18) . . ?
C1 C2 H2 121.1 . . ?
C3 C2 H2 121.1 . . ?
C4 C3 C2 121.50(18) . . ?
C4 C3 H3 119.2 . . ?
C2 C3 H3 119.2 . . ?
C3 C4 C5 120.03(18) . . ?
C3 C4 H4 120.0 . . ?
C5 C4 H4 120.0 . . ?
C6 C5 C4 118.91(18) . . ?
C6 C5 H5 120.5 . . ?
C4 C5 H5 120.5 . . ?
C5 C6 C1 120.69(17) . . ?
C5 C6 C7 130.30(17) . . ?
C1 C6 C7 109.01(15) . . ?
C6 C7 C8 115.37(15) . . ?
C6 C7 C10 101.88(14) . . ?
C8 C7 C10 105.70(15) . . ?
C6 C7 H7 110.0(13) . . ?
C8 C7 H7 111.9(13) . . ?
C10 C7 H7 111.5(13) . . ?
C9 C8 C7 104.45(15) . . ?
C9 C8 H8A 110.9 . . ?
C7 C8 H8A 110.9 . . ?
C9 C8 H8B 110.9 . . ?
C7 C8 H8B 110.9 . . ?
H8A C8 H8B 108.9 . . ?
O1 C9 N2 125.13(17) . . ?
O1 C9 C8 125.99(17) . . ?
N2 C9 C8 108.84(16) . . ?
N1 C10 N2 114.22(16) . . ?
N1 C10 C7 105.22(15) . . ?
N2 C10 C7 102.81(14) . . ?
N1 C10 H10 109.2(13) . . ?
N2 C10 H10 109.1(13) . . ?
C7 C10 H10 116.3(12) . . ?
N2 C11 H11A 109.5 . . ?
N2 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
N2 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N1 C12 H12A 109.5 . . ?
N1 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
N1 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C1 N1 C12 124.67(16) . . ?
C1 N1 C10 110.54(15) . . ?
C12 N1 C10 124.78(16) . . ?
C9 N2 C11 123.49(16) . . ?
C9 N2 C10 114.43(15) . . ?
C11 N2 C10 121.23(15) . . ?

_refine_diff_density_max         0.197
_refine_diff_density_min         -0.264
_refine_diff_density_rms         0.052

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

data_Compound-39
_database_code_depnum_ccdc_archive 'CCDC 1841090'
_audit_update_record             
;
2018-05-02 deposited with the CCDC.
2018-06-07 downloaded from the CCDC.
;

#=====================================================================
# start Validation Reply Form

_vrf_PLAT906_Compound-39         
;
RESPONSE:  The K value is large only for 
very weak reflections with Fc/Fcmax 
lower than 0.008.
;
# end Validation Reply Form 
#=====================================================================

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H16 N2 O2'
_chemical_formula_sum            'C13 H16 N2 O2'
_chemical_formula_weight         232.28

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           15
_space_group_name_H-M_alt        'C 2/c'
_space_group_name_Hall           '-C 2yc'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-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                   28.7011(14)
_cell_length_b                   9.3880(5)
_cell_length_c                   8.9139(4)
_cell_angle_alpha                90
_cell_angle_beta                 99.230(2)
_cell_angle_gamma                90
_cell_volume                     2370.7(2)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9903
_cell_measurement_theta_min      2.88
_cell_measurement_theta_max      30.54


_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    none
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_F_000             992
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.310
_exptl_crystal_size_mid          0.110
_exptl_crystal_size_min          0.060
_exptl_absorpt_coefficient_mu    0.089
_shelx_estimated_absorpt_T_min   0.973
_shelx_estimated_absorpt_T_max   0.995
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9641
_exptl_absorpt_correction_T_max  1
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was 
used for absorption correction. 
Krause, L., Herbst-Irmer, R., 
Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker D8 Venture PHOTON 100 CMOS'
_diffrn_measurement_method       'omega and phi scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            56256
_diffrn_reflns_av_unetI/netI     0.0210
_diffrn_reflns_av_R_equivalents  0.0409
_diffrn_reflns_limit_h_min       -39
_diffrn_reflns_limit_h_max       40
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.876
_diffrn_reflns_theta_max         30.582
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3644
_reflns_number_gt                3027
_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       'APEX3 v.2017.3-0 (Bruker AXS Inc., 2017)'
_computing_cell_refinement       'SAINT V.8.38A (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V.8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Xshell v.6.3.1 (Bruker AXS Inc., 2016)'
_computing_publication_material  'APEX3 v.2017.3-0 (Bruker AXS Inc., 2017)'


_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)+(0.0620P)²+1.8827P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3644
_refine_ls_number_parameters     159
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0619
_refine_ls_R_factor_gt           0.0483
_refine_ls_wR_factor_ref         0.1233
_refine_ls_wR_factor_gt          0.1152
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.063
_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 0.31679(3) 0.40789(9) 0.47475(10) 0.02007(19) Uani 1 1 d . . . . .
H1 H 0.2897(6) 0.4480(17) 0.4363(18) 0.024 Uiso 1 1 d . U . . .
O2 O 0.26548(3) 0.04945(9) 0.10213(10) 0.0223(2) Uani 1 1 d . . . . .
N1 N 0.31890(3) 0.23138(10) 0.12079(10) 0.01521(19) Uani 1 1 d . . . . .
N2 N 0.39198(4) 0.32624(12) 0.25278(11) 0.0219(2) Uani 1 1 d . . . . .
C1 C 0.28702(4) 0.14861(11) 0.17375(12) 0.0151(2) Uani 1 1 d . . . . .
C2 C 0.40663(4) 0.24810(12) 0.38400(12) 0.0152(2) Uani 1 1 d . . . . .
C3 C 0.36846(4) 0.21528(11) 0.45807(11) 0.0135(2) Uani 1 1 d . . . . .
C4 C 0.28180(4) 0.19688(12) 0.33158(12) 0.0153(2) Uani 1 1 d . . . . .
H4A H 0.281902 0.114482 0.400941 0.018 Uiso 1 1 calc R U . . .
H4B H 0.252136 0.250994 0.330272 0.018 Uiso 1 1 calc R U . . .
C5 C 0.32484(4) 0.29209(11) 0.38054(11) 0.0135(2) Uani 1 1 d . . . . .
C6 C 0.34104(4) 0.33856(11) 0.22914(12) 0.0153(2) Uani 1 1 d . . . . .
H6 H 0.330298 0.437205 0.198554 0.018 Uiso 1 1 calc R U . . .
C7 C 0.33161(4) 0.21703(13) -0.02979(12) 0.0198(2) Uani 1 1 d . . . . .
H7A H 0.364633 0.186865 -0.020696 0.030 Uiso 1 1 calc R U . . .
H7B H 0.327533 0.308860 -0.082535 0.030 Uiso 1 1 calc R U . . .
H7C H 0.311242 0.145665 -0.087720 0.030 Uiso 1 1 calc R U . . .
C8 C 0.41955(5) 0.07858(13) 0.64243(14) 0.0232(3) Uani 1 1 d . . . . .
H8 H 0.424275 0.018876 0.729602 0.028 Uiso 1 1 calc R U . . .
C9 C 0.37448(4) 0.13039(12) 0.58629(12) 0.0186(2) Uani 1 1 d . . . . .
H9 H 0.348424 0.107616 0.635469 0.022 Uiso 1 1 calc R U . . .
C10 C 0.45180(4) 0.19967(13) 0.44130(13) 0.0195(2) Uani 1 1 d . . . . .
H10 H 0.478035 0.224001 0.393613 0.023 Uiso 1 1 calc R U . . .
C11 C 0.45734(4) 0.11443(13) 0.57072(14) 0.0221(2) Uani 1 1 d . . . . .
H11 H 0.487890 0.079853 0.611040 0.027 Uiso 1 1 calc R U . . .
C12 C 0.42156(4) 0.42497(14) 0.18577(13) 0.0216(2) Uani 1 1 d . . . . .
H12A H 0.403882 0.459721 0.088096 0.026 Uiso 1 1 calc R U . . .
H12B H 0.449728 0.373394 0.163331 0.026 Uiso 1 1 calc R U . . .
C13 C 0.43760(5) 0.55171(15) 0.28532(16) 0.0312(3) Uani 1 1 d . . . . .
H13A H 0.409967 0.603800 0.307978 0.047 Uiso 1 1 calc R U . . .
H13B H 0.456748 0.614771 0.232167 0.047 Uiso 1 1 calc R U . . .
H13C H 0.456499 0.518753 0.380379 0.047 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 C5 1.4151(13) . ?
O1 H1 0.883(17) . ?
O2 C1 1.2368(13) . ?
N1 C1 1.3426(14) . ?
N1 C7 1.4526(14) . ?
N1 C6 1.4670(13) . ?
N2 C2 1.3876(14) . ?
N2 C6 1.4479(15) . ?
N2 C12 1.4489(15) . ?
C1 C4 1.5082(15) . ?
C2 C10 1.3914(15) . ?
C2 C3 1.4010(15) . ?
C3 C9 1.3812(14) . ?
C3 C5 1.5124(14) . ?
C4 C5 1.5304(15) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.5585(15) . ?
C6 H6 1.0000 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C11 1.3859(19) . ?
C8 C9 1.3972(16) . ?
C8 H8 0.9500 . ?
C9 H9 0.9500 . ?
C10 C11 1.3919(17) . ?
C10 H10 0.9500 . ?
C11 H11 0.9500 . ?
C12 C13 1.5114(18) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 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
C5 O1 H1 108.4(10) . . ?
C1 N1 C7 123.88(9) . . ?
C1 N1 C6 114.41(9) . . ?
C7 N1 C6 121.70(9) . . ?
C2 N2 C6 109.10(9) . . ?
C2 N2 C12 124.57(10) . . ?
C6 N2 C12 122.25(9) . . ?
O2 C1 N1 124.51(10) . . ?
O2 C1 C4 126.27(10) . . ?
N1 C1 C4 109.22(9) . . ?
N2 C2 C10 128.37(11) . . ?
N2 C2 C3 111.06(10) . . ?
C10 C2 C3 120.54(10) . . ?
C9 C3 C2 120.88(10) . . ?
C9 C3 C5 129.62(10) . . ?
C2 C3 C5 109.41(9) . . ?
C1 C4 C5 104.20(9) . . ?
C1 C4 H4A 110.9 . . ?
C5 C4 H4A 110.9 . . ?
C1 C4 H4B 110.9 . . ?
C5 C4 H4B 110.9 . . ?
H4A C4 H4B 108.9 . . ?
O1 C5 C3 107.28(8) . . ?
O1 C5 C4 114.63(9) . . ?
C3 C5 C4 115.02(9) . . ?
O1 C5 C6 113.49(9) . . ?
C3 C5 C6 100.90(8) . . ?
C4 C5 C6 104.82(8) . . ?
N2 C6 N1 111.20(9) . . ?
N2 C6 C5 106.63(8) . . ?
N1 C6 C5 102.72(8) . . ?
N2 C6 H6 111.9 . . ?
N1 C6 H6 111.9 . . ?
C5 C6 H6 111.9 . . ?
N1 C7 H7A 109.5 . . ?
N1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
N1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C11 C8 C9 119.88(11) . . ?
C11 C8 H8 120.1 . . ?
C9 C8 H8 120.1 . . ?
C3 C9 C8 118.88(11) . . ?
C3 C9 H9 120.6 . . ?
C8 C9 H9 120.6 . . ?
C2 C10 C11 117.89(11) . . ?
C2 C10 H10 121.1 . . ?
C11 C10 H10 121.1 . . ?
C8 C11 C10 121.88(11) . . ?
C8 C11 H11 119.1 . . ?
C10 C11 H11 119.1 . . ?
N2 C12 C13 113.90(10) . . ?
N2 C12 H12A 108.8 . . ?
C13 C12 H12A 108.8 . . ?
N2 C12 H12B 108.8 . . ?
C13 C12 H12B 108.8 . . ?
H12A C12 H12B 107.7 . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 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
C7 N1 C1 O2 1.34(17) . . . . ?
C6 N1 C1 O2 -177.78(10) . . . . ?
C7 N1 C1 C4 -178.24(10) . . . . ?
C6 N1 C1 C4 2.64(12) . . . . ?
C6 N2 C2 C10 173.45(11) . . . . ?
C12 N2 C2 C10 -28.96(19) . . . . ?
C6 N2 C2 C3 -4.51(13) . . . . ?
C12 N2 C2 C3 153.08(11) . . . . ?
N2 C2 C3 C9 175.94(10) . . . . ?
C10 C2 C3 C9 -2.21(16) . . . . ?
N2 C2 C3 C5 -7.10(13) . . . . ?
C10 C2 C3 C5 174.76(10) . . . . ?
O2 C1 C4 C5 165.12(11) . . . . ?
N1 C1 C4 C5 -15.31(11) . . . . ?
C9 C3 C5 O1 72.05(14) . . . . ?
C2 C3 C5 O1 -104.56(10) . . . . ?
C9 C3 C5 C4 -56.76(15) . . . . ?
C2 C3 C5 C4 126.62(10) . . . . ?
C9 C3 C5 C6 -168.93(11) . . . . ?
C2 C3 C5 C6 14.45(11) . . . . ?
C1 C4 C5 O1 146.19(9) . . . . ?
C1 C4 C5 C3 -88.73(10) . . . . ?
C1 C4 C5 C6 21.10(11) . . . . ?
C2 N2 C6 N1 -97.48(11) . . . . ?
C12 N2 C6 N1 104.31(12) . . . . ?
C2 N2 C6 C5 13.76(12) . . . . ?
C12 N2 C6 C5 -144.44(11) . . . . ?
C1 N1 C6 N2 124.62(10) . . . . ?
C7 N1 C6 N2 -54.52(13) . . . . ?
C1 N1 C6 C5 10.91(12) . . . . ?
C7 N1 C6 C5 -168.23(9) . . . . ?
O1 C5 C6 N2 97.73(10) . . . . ?
C3 C5 C6 N2 -16.71(11) . . . . ?
C4 C5 C6 N2 -136.47(9) . . . . ?
O1 C5 C6 N1 -145.25(9) . . . . ?
C3 C5 C6 N1 100.32(9) . . . . ?
C4 C5 C6 N1 -19.45(10) . . . . ?
C2 C3 C9 C8 0.67(17) . . . . ?
C5 C3 C9 C8 -175.61(11) . . . . ?
C11 C8 C9 C3 0.94(18) . . . . ?
N2 C2 C10 C11 -175.75(11) . . . . ?
C3 C2 C10 C11 2.04(16) . . . . ?
C9 C8 C11 C10 -1.07(19) . . . . ?
C2 C10 C11 C8 -0.43(18) . . . . ?
C2 N2 C12 C13 -63.90(16) . . . . ?
C6 N2 C12 C13 90.88(14) . . . . ?

_refine_diff_density_max         0.318
_refine_diff_density_min         -0.365
_refine_diff_density_rms         0.079

