# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2024

####################################################################### 
# 
# 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_mo_d8v191145_0m
_database_code_depnum_ccdc_archive 'CCDC 2072311'
loop_
_audit_author_name
_audit_author_address
'Yong Deng'
;Department of Chemistry, Shanghai University
China
;
_audit_update_record             
;
2021-03-23 deposited with the CCDC.	2024-01-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C10 H8 N2 O2'
_chemical_formula_weight         188.18

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                   6.1062(2)
_cell_length_b                   7.7462(4)
_cell_length_c                   19.4842(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     921.60(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    193(2)
_cell_measurement_reflns_used    3097
_cell_measurement_theta_min      6.273
_cell_measurement_theta_max      54.960

_exptl_crystal_description       prismatic
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.356
_exptl_crystal_F_000             392
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.160
_exptl_crystal_size_mid          0.130
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.097
_shelx_estimated_absorpt_T_min   0.985
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6590
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      193(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            4576
_diffrn_reflns_av_unetI/netI     0.0265
_diffrn_reflns_av_R_equivalents  0.0203
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.090
_diffrn_reflns_theta_max         25.997
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.987
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.987
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             1799
_reflns_number_gt                1691
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.672
_reflns_Friedel_fraction_max     0.990
_reflns_Friedel_fraction_full    0.991

_reflns_special_details          
; 
 Reflections were merged by SHELXL according to the crystal 
 class for the calculation of statistics and refinement. 
  
 _reflns_Friedel_fraction is defined as the number of unique 
 Friedel pairs measured divided by the number that would be 
 possible theoretically, ignoring centric projections and 
 systematic absences. 
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.0333P)²+0.1672P] 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_abs_structure_details 
; 
 Flack x determined using 651 quotients [(I+)-(I-)]/[(I+)+(I-)] 
 (Parsons and Flack (2004), Acta Cryst. A60, s61). 
;
_refine_ls_abs_structure_Flack   -0.8(6)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         1799
_refine_ls_number_parameters     127
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0349
_refine_ls_R_factor_gt           0.0317
_refine_ls_wR_factor_ref         0.0773
_refine_ls_wR_factor_gt          0.0747
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.046
_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
N1 N 0.7323(3) 0.6706(2) 0.56941(8) 0.0320(4) Uani 1 1 d . . . . .
N2 N 0.7321(4) 0.3269(3) 0.46301(11) 0.0566(6) Uani 1 1 d . . . . .
O1 O 0.9184(2) 0.7095(2) 0.54995(7) 0.0458(4) Uani 1 1 d . . . . .
O2 O 0.6387(2) 0.77949(19) 0.61912(7) 0.0396(4) Uani 1 1 d . . . . .
C1 C 0.6024(3) 0.5438(2) 0.55322(9) 0.0303(4) Uani 1 1 d . . . . .
C2 C 0.3943(3) 0.5506(3) 0.59212(10) 0.0352(5) Uani 1 1 d . . . . .
H2A H 0.3903 0.4629 0.6291 0.042 Uiso 1 1 calc R U . . .
H2B H 0.2659 0.5350 0.5617 0.042 Uiso 1 1 calc R U . . .
C3 C 0.4047(3) 0.7346(2) 0.62135(9) 0.0315(4) Uani 1 1 d . . . . .
H3 H 0.3209 0.8146 0.5908 0.038 Uiso 1 1 calc R U . . .
C4 C 0.3248(3) 0.7533(2) 0.69395(9) 0.0311(4) Uani 1 1 d . . . . .
C5 C 0.1325(3) 0.8422(3) 0.70560(10) 0.0377(5) Uani 1 1 d . . . . .
H5 H 0.0587 0.8963 0.6684 0.045 Uiso 1 1 calc R U . . .
C6 C 0.0469(4) 0.8528(3) 0.77103(12) 0.0499(6) Uani 1 1 d . . . . .
H6 H -0.0861 0.9133 0.7788 0.060 Uiso 1 1 calc R U . . .
C7 C 0.1542(4) 0.7756(3) 0.82517(11) 0.0519(6) Uani 1 1 d . . . . .
H7 H 0.0946 0.7816 0.8701 0.062 Uiso 1 1 calc R U . . .
C8 C 0.3496(4) 0.6890(3) 0.81360(11) 0.0498(6) Uani 1 1 d . . . . .
H8 H 0.4253 0.6373 0.8509 0.060 Uiso 1 1 calc R U . . .
C9 C 0.4341(4) 0.6780(3) 0.74818(11) 0.0403(5) Uani 1 1 d . . . . .
H9 H 0.5678 0.6183 0.7404 0.048 Uiso 1 1 calc R U . . .
C10 C 0.6739(3) 0.4232(3) 0.50330(10) 0.0368(5) 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
N1 O1 1.235(2) . ?
N1 C1 1.301(3) . ?
N1 O2 1.406(2) . ?
N2 C10 1.139(3) . ?
O2 C3 1.471(2) . ?
C1 C10 1.418(3) . ?
C1 C2 1.481(3) . ?
C2 C3 1.536(3) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.503(3) . ?
C3 H3 1.0000 . ?
C4 C9 1.379(3) . ?
C4 C5 1.380(3) . ?
C5 C6 1.380(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.378(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.387(4) . ?
C7 H7 0.9500 . ?
C8 C9 1.378(3) . ?
C8 H8 0.9500 . ?
C9 H9 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
O1 N1 C1 132.11(18) . . ?
O1 N1 O2 116.06(16) . . ?
C1 N1 O2 111.83(15) . . ?
N1 O2 C3 105.87(14) . . ?
N1 C1 C10 118.41(18) . . ?
N1 C1 C2 111.86(16) . . ?
C10 C1 C2 129.73(18) . . ?
C1 C2 C3 100.78(16) . . ?
C1 C2 H2A 111.6 . . ?
C3 C2 H2A 111.6 . . ?
C1 C2 H2B 111.6 . . ?
C3 C2 H2B 111.6 . . ?
H2A C2 H2B 109.4 . . ?
O2 C3 C4 108.68(15) . . ?
O2 C3 C2 104.42(15) . . ?
C4 C3 C2 115.16(16) . . ?
O2 C3 H3 109.5 . . ?
C4 C3 H3 109.5 . . ?
C2 C3 H3 109.5 . . ?
C9 C4 C5 119.79(18) . . ?
C9 C4 C3 121.51(18) . . ?
C5 C4 C3 118.64(17) . . ?
C4 C5 C6 120.2(2) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C7 C6 C5 120.1(2) . . ?
C7 C6 H6 119.9 . . ?
C5 C6 H6 119.9 . . ?
C6 C7 C8 119.6(2) . . ?
C6 C7 H7 120.2 . . ?
C8 C7 H7 120.2 . . ?
C9 C8 C7 120.2(2) . . ?
C9 C8 H8 119.9 . . ?
C7 C8 H8 119.9 . . ?
C8 C9 C4 120.1(2) . . ?
C8 C9 H9 120.0 . . ?
C4 C9 H9 120.0 . . ?
N2 C10 C1 179.6(3) . . ?

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 N1 O2 C3 166.46(16) . . . . ?
C1 N1 O2 C3 -14.3(2) . . . . ?
O1 N1 C1 C10 -1.3(3) . . . . ?
O2 N1 C1 C10 179.70(17) . . . . ?
O1 N1 C1 C2 178.73(19) . . . . ?
O2 N1 C1 C2 -0.3(2) . . . . ?
N1 C1 C2 C3 13.9(2) . . . . ?
C10 C1 C2 C3 -166.1(2) . . . . ?
N1 O2 C3 C4 145.48(15) . . . . ?
N1 O2 C3 C2 22.09(19) . . . . ?
C1 C2 C3 O2 -21.23(19) . . . . ?
C1 C2 C3 C4 -140.31(17) . . . . ?
O2 C3 C4 C9 -50.4(2) . . . . ?
C2 C3 C4 C9 66.3(2) . . . . ?
O2 C3 C4 C5 132.31(18) . . . . ?
C2 C3 C4 C5 -111.0(2) . . . . ?
C9 C4 C5 C6 -1.4(3) . . . . ?
C3 C4 C5 C6 175.9(2) . . . . ?
C4 C5 C6 C7 0.5(3) . . . . ?
C5 C6 C7 C8 0.7(4) . . . . ?
C6 C7 C8 C9 -1.0(3) . . . . ?
C7 C8 C9 C4 0.2(3) . . . . ?
C5 C4 C9 C8 1.1(3) . . . . ?
C3 C4 C9 C8 -176.17(19) . . . . ?

_refine_diff_density_max         0.121
_refine_diff_density_min         -0.126
_refine_diff_density_rms         0.027

_shelxl_version_number           2013-4



_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: DCM'
####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 2072312'
loop_
_audit_author_name
_audit_author_address
'Yong Deng'
;Department of Chemistry, Shanghai University
China
;
_audit_update_record             
;
2021-03-23 deposited with the CCDC.	2024-01-08 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H18 N2 O2'
_chemical_formula_weight         282.33

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           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                   9.5508(7)
_cell_length_b                   5.7679(4)
_cell_length_c                   13.0789(10)
_cell_angle_alpha                90
_cell_angle_beta                 104.975(4)
_cell_angle_gamma                90
_cell_volume                     696.02(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2100
_cell_measurement_theta_min      2.5
_cell_measurement_theta_max      25.0

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.347
_exptl_crystal_F_000             300
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.15
_exptl_absorpt_coefficient_mu    0.717
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.857
_exptl_absorpt_correction_T_max  0.898
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   ?

_diffrn_measurement_device_type  'Bruker SMART 1000'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 10.0
_diffrn_reflns_number            3744
_diffrn_reflns_av_unetI/netI     0.0629
_diffrn_reflns_av_R_equivalents  0.0374
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.498
_diffrn_reflns_theta_max         66.587
_diffrn_reflns_theta_full        66.587
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.923
_diffrn_reflns_point_group_measured_fraction_full 0.923
_reflns_number_total             2273
_reflns_number_gt                2143
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.669
_reflns_Friedel_fraction_max     0.830
_reflns_Friedel_fraction_full    0.830

_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-2018/3 (Sheldrick, 2018)'
_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)+(0.1032P)²] 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_abs_structure_details 
;
 Flack x determined using 823 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.2(2)
_chemical_absolute_configuration s
_refine_ls_number_reflns         2273
_refine_ls_number_parameters     190
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0575
_refine_ls_R_factor_gt           0.0549
_refine_ls_wR_factor_ref         0.1457
_refine_ls_wR_factor_gt          0.1426
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_restrained_S_all      1.089
_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
O2 O 0.4668(2) 0.1194(4) 0.35413(17) 0.0393(5) Uani 1 1 d . . . . .
O1 O 0.2726(2) 0.3607(5) 0.29510(19) 0.0460(6) Uani 1 1 d . . . . .
N2 N 0.3757(3) 0.2088(5) 0.2607(2) 0.0395(6) Uani 1 1 d . . . . .
N1 N 0.5703(3) 0.1562(6) 0.0809(3) 0.0496(7) Uani 1 1 d . . . . .
C13 C 0.1048(3) 0.6310(5) 0.1861(2) 0.0356(7) Uani 1 1 d . . . . .
C14 C 0.0232(4) 0.4613(6) 0.1200(3) 0.0396(7) Uani 1 1 d . . . . .
H14 H 0.066735 0.318242 0.109328 0.048 Uiso 1 1 calc R U . . .
C15 C -0.1215(4) 0.5033(6) 0.0701(3) 0.0417(7) Uani 1 1 d . . . . .
H15 H -0.176894 0.388825 0.024983 0.050 Uiso 1 1 calc R U . . .
C7 C 0.5276(3) 0.2504(6) 0.1430(3) 0.0393(7) Uani 1 1 d . . . . .
C4 C 0.5863(3) 0.4608(5) 0.3191(2) 0.0353(7) Uani 1 1 d . . . . .
H4 H 0.571125 0.627051 0.335128 0.042 Uiso 1 1 calc R U . . .
C12 C 0.7690(3) 0.1623(6) 0.3603(2) 0.0373(7) Uani 1 1 d . . . . .
H12A H 0.708892 0.051706 0.309576 0.045 Uiso 1 1 calc R U . . .
H12B H 0.871994 0.114448 0.378076 0.045 Uiso 1 1 calc R U . . .
C5 C 0.5621(3) 0.3017(5) 0.4085(2) 0.0368(7) Uani 1 1 d . . . . .
H5 H 0.521340 0.386932 0.460883 0.044 Uiso 1 1 calc R U . . .
C3 C 0.4686(3) 0.3793(5) 0.2204(2) 0.0348(6) Uani 1 1 d . . . . .
C8 C 0.7465(3) 0.4160(6) 0.3224(2) 0.0387(7) Uani 1 1 d . . . . .
H8 H 0.773304 0.449704 0.254920 0.046 Uiso 1 1 calc R U . . .
C2 C 0.3602(3) 0.5635(5) 0.1666(2) 0.0388(7) Uani 1 1 d . . . . .
H2A H 0.305367 0.513521 0.095005 0.047 Uiso 1 1 calc R U . . .
H2B H 0.408989 0.712784 0.161109 0.047 Uiso 1 1 calc R U . . .
C1 C 0.2617(3) 0.5821(6) 0.2416(2) 0.0395(7) Uani 1 1 d . . . . .
H1 H 0.298967 0.706771 0.294846 0.047 Uiso 1 1 calc R U . . .
C17 C -0.1045(3) 0.8809(6) 0.1495(2) 0.0406(7) Uani 1 1 d . . . . .
H17 H -0.147755 1.024917 0.158903 0.049 Uiso 1 1 calc R U . . .
C16 C -0.1857(4) 0.7110(6) 0.0859(2) 0.0409(7) Uani 1 1 d . . . . .
H16 H -0.285394 0.737113 0.053015 0.049 Uiso 1 1 calc R U . . .
C18 C 0.0410(3) 0.8398(6) 0.1998(2) 0.0384(7) Uani 1 1 d . . . . .
H18 H 0.096451 0.956025 0.243747 0.046 Uiso 1 1 calc R U . . .
C9 C 0.8386(4) 0.5416(6) 0.4202(3) 0.0463(8) Uani 1 1 d . . . . .
H9A H 0.809593 0.706224 0.421138 0.056 Uiso 1 1 calc R U . . .
H9B H 0.942988 0.533693 0.422626 0.056 Uiso 1 1 calc R U . . .
C10 C 0.8054(3) 0.4054(6) 0.5137(2) 0.0424(7) Uani 1 1 d . . . . .
H10A H 0.895685 0.350154 0.563606 0.051 Uiso 1 1 calc R U . . .
H10B H 0.750868 0.502346 0.552669 0.051 Uiso 1 1 calc R U . . .
C11 C 0.7128(4) 0.2011(6) 0.4581(2) 0.0381(7) Uani 1 1 d . . . . .
H11 H 0.714025 0.060764 0.503219 0.046 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 N2 1.402(4) . ?
O2 C5 1.451(4) . ?
O1 C1 1.447(4) . ?
O1 N2 1.473(4) . ?
N2 C3 1.508(4) . ?
N1 C7 1.137(5) . ?
C13 C18 1.382(5) . ?
C13 C14 1.402(5) . ?
C13 C1 1.514(4) . ?
C14 C15 1.389(5) . ?
C15 C16 1.385(5) . ?
C7 C3 1.479(4) . ?
C4 C8 1.541(4) . ?
C4 C5 1.550(4) . ?
C4 C3 1.550(4) . ?
C12 C11 1.526(4) . ?
C12 C8 1.542(4) . ?
C5 C11 1.532(4) . ?
C3 C2 1.523(4) . ?
C8 C9 1.534(5) . ?
C2 C1 1.529(4) . ?
C17 C16 1.386(5) . ?
C17 C18 1.395(5) . ?
C9 C10 1.554(5) . ?
C10 C11 1.539(5) . ?

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
N2 O2 C5 109.3(2) . . ?
C1 O1 N2 110.3(2) . . ?
O2 N2 O1 105.4(2) . . ?
O2 N2 C3 104.8(2) . . ?
O1 N2 C3 102.7(2) . . ?
C18 C13 C14 119.7(3) . . ?
C18 C13 C1 121.0(3) . . ?
C14 C13 C1 119.3(3) . . ?
C15 C14 C13 119.6(3) . . ?
C16 C15 C14 120.4(3) . . ?
N1 C7 C3 177.6(3) . . ?
C8 C4 C5 102.7(2) . . ?
C8 C4 C3 118.3(3) . . ?
C5 C4 C3 103.4(2) . . ?
C11 C12 C8 94.6(2) . . ?
O2 C5 C11 109.5(2) . . ?
O2 C5 C4 104.8(2) . . ?
C11 C5 C4 103.7(2) . . ?
C7 C3 N2 105.9(2) . . ?
C7 C3 C2 111.6(2) . . ?
N2 C3 C2 103.0(2) . . ?
C7 C3 C4 113.6(2) . . ?
N2 C3 C4 105.8(2) . . ?
C2 C3 C4 115.7(3) . . ?
C9 C8 C4 107.2(3) . . ?
C9 C8 C12 100.2(2) . . ?
C4 C8 C12 102.9(2) . . ?
C3 C2 C1 102.1(2) . . ?
O1 C1 C13 109.6(3) . . ?
O1 C1 C2 105.6(2) . . ?
C13 C1 C2 113.7(3) . . ?
C16 C17 C18 119.9(3) . . ?
C15 C16 C17 120.0(3) . . ?
C13 C18 C17 120.3(3) . . ?
C8 C9 C10 103.2(3) . . ?
C11 C10 C9 103.0(3) . . ?
C12 C11 C5 101.3(2) . . ?
C12 C11 C10 103.0(3) . . ?
C5 C11 C10 105.8(3) . . ?

_refine_diff_density_max         0.330
_refine_diff_density_min         -0.234
_refine_diff_density_rms         0.061



_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: DCM'
