# Supplementary Information (SI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2026

####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 2433435'
loop_
_audit_author_name
_audit_author_address
'Li-Ming Zhang'
;Dalian Institute of Chemical Physics, Chinese Academy of Sciences
China
;
_audit_update_record             
;
2025-03-24 deposited with the CCDC.	2025-12-03 downloaded from the CCDC.
;
_audit_creation_date             2025-03-24
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H20 N2 O'
_chemical_formula_sum            'C12 H20 N2 O'
_chemical_formula_weight         208.30
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.8209(3)
_cell_length_b                   9.6111(4)
_cell_length_c                   11.5153(5)
_cell_angle_alpha                74.895(4)
_cell_angle_beta                 88.396(4)
_cell_angle_gamma                84.626(4)
_cell_volume                     619.23(5)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3436
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      74.0860
_cell_measurement_theta_min      3.9510
_shelx_estimated_absorpt_T_max   0.936
_shelx_estimated_absorpt_T_min   0.901
_exptl_absorpt_coefficient_mu    0.563
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.117
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             228
_exptl_crystal_size_max          0.19
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0532
_diffrn_reflns_av_unetI/netI     0.0342
_diffrn_reflns_Laue_measured_fraction_full 0.981
_diffrn_reflns_Laue_measured_fraction_max 0.921
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            11389
_diffrn_reflns_point_group_measured_fraction_full 0.981
_diffrn_reflns_point_group_measured_fraction_max 0.921
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         79.638
_diffrn_reflns_theta_min         3.976
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.921
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1463
_reflns_number_total             2496
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.277
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     143
_refine_ls_number_reflns         2496
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1014
_refine_ls_R_factor_gt           0.0693
_refine_ls_restrained_S_all      1.087
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1394P)²+0.0252P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2201
_refine_ls_wR_factor_ref         0.2524
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C4(H4), C11(H11), C12(H12)
2.b Secondary CH2 refined with riding coordinates:
 C7(H7A,H7B), C8(H8A,H8B), C10(H10A,H10B)
2.c Aromatic/amide H refined with riding coordinates:
 C9(H9)
2.d Idealised Me refined as rotating group:
 C13(H13A,H13B,H13C), C1(H1A,H1B,H1C), C2(H2A,H2B,H2C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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 0.4325(3) 0.4199(2) 0.33625(19) 0.0760(6) Uani 1 1 d . . . . .
O2 O 0.4473(4) 0.2759(2) 0.53540(19) 0.0933(6) Uani 1 1 d . . . . .
N3 N 0.5128(4) 0.5528(2) 0.3023(2) 0.0839(7) Uani 1 1 d . . . . .
C4 C 0.3089(4) 0.3785(3) 0.4505(2) 0.0794(7) Uani 1 1 d . . . . .
H4 H 0.2800 0.4651 0.4805 0.095 Uiso 1 1 calc R . . . .
C5 C 0.4911(4) 0.3404(3) 0.2566(2) 0.0806(7) Uani 1 1 d . . . . .
C6 C 0.6210(5) 0.5565(3) 0.1971(3) 0.0924(9) Uani 1 1 d . . . . .
C7 C 0.0777(4) 0.3251(3) 0.4366(3) 0.0884(8) Uani 1 1 d . . . . .
H7A H -0.0052 0.3960 0.3722 0.106 Uiso 1 1 calc R . . . .
H7B H -0.0099 0.3214 0.5100 0.106 Uiso 1 1 calc R . . . .
C8 C 0.0823(5) 0.1780(3) 0.4098(3) 0.0947(9) Uani 1 1 d . . . . .
H8A H 0.1773 0.1089 0.4701 0.114 Uiso 1 1 calc R . . . .
H8B H -0.0732 0.1481 0.4191 0.114 Uiso 1 1 calc R . . . .
C9 C 0.6119(5) 0.4266(4) 0.1671(3) 0.0947(9) Uani 1 1 d . . . . .
H9 H 0.6757 0.4027 0.0991 0.114 Uiso 1 1 calc R . . . .
C10 C 0.4306(5) 0.1895(3) 0.2728(3) 0.0958(9) Uani 1 1 d . . . . .
H10A H 0.5101 0.1285 0.3434 0.115 Uiso 1 1 calc R . . . .
H10B H 0.4885 0.1563 0.2039 0.115 Uiso 1 1 calc R . . . .
C11 C 0.1707(5) 0.1686(3) 0.2871(3) 0.0978(9) Uani 1 1 d . . . . .
H11 H 0.0863 0.2451 0.2259 0.117 Uiso 1 1 calc R . . . .
C12 C 0.7380(6) 0.6879(5) 0.1325(4) 0.1388(16) Uani 1 1 d . . . . .
H12 H 0.7059 0.6775 0.0523 0.167 Uiso 1 1 calc R . . . .
C13 C 0.9790(8) 0.6663(6) 0.1201(8) 0.228(4) Uani 1 1 d . . . . .
H13A H 1.0532 0.7003 0.1795 0.342 Uiso 1 1 calc GR . . . .
H13B H 1.0243 0.7189 0.0412 0.342 Uiso 1 1 calc GR . . . .
H13C H 1.0238 0.5651 0.1309 0.342 Uiso 1 1 calc GR . . . .
C1 C 0.1261(7) 0.0230(4) 0.2672(4) 0.1301(13) Uani 1 1 d . . . . .
H1A H 0.2173 -0.0528 0.3225 0.195 Uiso 1 1 calc GR . . . .
H1B H 0.1673 0.0214 0.1862 0.195 Uiso 1 1 calc GR . . . .
H1C H -0.0345 0.0085 0.2804 0.195 Uiso 1 1 calc GR . . . .
C2 C 0.6161(9) 0.8193(5) 0.1146(7) 0.194(3) Uani 1 1 d . . . . .
H2A H 0.4880 0.8239 0.0626 0.291 Uiso 1 1 calc GR . . . .
H2B H 0.7142 0.8938 0.0780 0.291 Uiso 1 1 calc GR . . . .
H2C H 0.5602 0.8330 0.1904 0.291 Uiso 1 1 calc GR . . . .
H2 H 0.477(6) 0.324(4) 0.596(3) 0.124(12) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 N3 1.358(3) . ?
N1 C4 1.461(3) . ?
N1 C5 1.357(3) . ?
O2 C4 1.403(3) . ?
N3 C6 1.343(3) . ?
C4 C7 1.511(4) . ?
C5 C9 1.366(4) . ?
C5 C10 1.488(4) . ?
C6 C9 1.385(5) . ?
C6 C12 1.501(5) . ?
C7 C8 1.521(4) . ?
C8 C11 1.513(4) . ?
C10 C11 1.544(4) . ?
C11 C1 1.521(4) . ?
C12 C13 1.407(5) . ?
C12 C2 1.359(6) . ?

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
N3 N1 C4 118.9(2) . . ?
C5 N1 N3 112.1(2) . . ?
C5 N1 C4 128.9(2) . . ?
C6 N3 N1 104.6(2) . . ?
N1 C4 C7 112.4(2) . . ?
O2 C4 N1 110.15(19) . . ?
O2 C4 C7 111.6(2) . . ?
N1 C5 C9 105.9(3) . . ?
N1 C5 C10 123.6(2) . . ?
C9 C5 C10 130.5(3) . . ?
N3 C6 C9 110.6(3) . . ?
N3 C6 C12 120.1(3) . . ?
C9 C6 C12 129.3(3) . . ?
C4 C7 C8 116.5(2) . . ?
C11 C8 C7 116.6(2) . . ?
C5 C9 C6 106.8(3) . . ?
C5 C10 C11 115.4(2) . . ?
C8 C11 C10 111.5(3) . . ?
C8 C11 C1 109.8(3) . . ?
C1 C11 C10 110.0(2) . . ?
C13 C12 C6 115.7(4) . . ?
C2 C12 C6 118.1(3) . . ?
C2 C12 C13 124.7(4) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# 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_22
_database_code_depnum_ccdc_archive 'CCDC 2433436'
loop_
_audit_author_name
_audit_author_address
'Li-Ming Zhang'
;Dalian Institute of Chemical Physics, Chinese Academy of Sciences
China
;
_audit_update_record             
;
2025-03-24 deposited with the CCDC.	2025-12-03 downloaded from the CCDC.
;
_audit_creation_date             2024-01-22
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '0.75(C12 H14 N2), 0.25(C12 H10.97 N2)'
_chemical_formula_sum            'C12 H14 N2'
_chemical_formula_weight         186.25
_chemical_absolute_configuration ?
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           7
_space_group_name_H-M_alt        'P 1 c 1'
_space_group_name_Hall           'P -2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'

_cell_length_a                   11.4118(6)
_cell_length_b                   10.9978(7)
_cell_length_c                   18.1346(10)
_cell_angle_alpha                90
_cell_angle_beta                 90.638(5)
_cell_angle_gamma                90
_cell_volume                     2275.8(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    6822
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      76.5150
_cell_measurement_theta_min      3.8440
_shelx_estimated_absorpt_T_max   0.947
_shelx_estimated_absorpt_T_min   0.897
_exptl_absorpt_coefficient_mu    0.504
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            ?
_exptl_crystal_density_diffrn    1.087
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             800
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.11
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0724
_diffrn_reflns_av_unetI/netI     0.0596
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            30705
_diffrn_reflns_point_group_measured_fraction_full 0.838
_diffrn_reflns_point_group_measured_fraction_max 0.796
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         76.709
_diffrn_reflns_theta_min         3.874
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'multiwire proportional'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_source                   ?
_reflns_Friedel_coverage         0.623
_reflns_Friedel_fraction_full    0.676
_reflns_Friedel_fraction_max     0.612
_reflns_number_gt                3682
_reflns_number_total             7636
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       ?
_computing_data_collection       ?
_computing_data_reduction        ?
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.169
_refine_diff_density_min         -0.177
_refine_diff_density_rms         0.032
_refine_ls_abs_structure_details 
;
 Flack x determined using 1165 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(5)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.942
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     531
_refine_ls_number_reflns         7636
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1222
_refine_ls_R_factor_gt           0.0635
_refine_ls_restrained_S_all      0.942
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1011P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1584
_refine_ls_wR_factor_ref         0.1980
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Sof(C56)=Sof(H56)=1-FVAR(1)
 Sof(H46A)=Sof(H46B)=Sof(H46C)=Sof(C1)=Sof(H1A)=Sof(H1B)=Sof(H1C)=FVAR(1)
3.a Ternary CH refined with riding coordinates:
 C25(H25), C33(H33), C53(H53)
3.b Aromatic/amide H refined with riding coordinates:
 C7(H7), N11(H11), C17(H17), C23(H23), C24(H24), C28(H28), C29(H29), C32(H32),
 C34(H34), C35(H35), C36(H36), C40(H40), C42(H42), C43(H43), C44(H44), C45(H45),
  C48(H48), C50(H50), C55(H55), N19(H19), C22(H22), C27(H27), C30(H30),
 C31(H31), C37(H37), C41(H41), C56(H56)
3.c Idealised Me refined as rotating group:
 C46(H46A,H46B,H46C), C49(H49A,H49B,H49C), C51(H51A,H51B,H51C), C52(H52A,H52B,
 H52C), C54(H54A,H54B,H54C), C39(H39A,H39B,H39C), C47(H47A,H47B,H47C), C1(H1A,
 H1B,H1C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
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 -0.0757(5) -0.1764(5) -0.2638(3) 0.1029(15) Uani 1 1 d . . . . .
C2 C -0.2136(5) -0.2735(5) -0.2132(3) 0.0877(14) Uani 1 1 d . . . . .
N3 N -0.1104(4) -0.2891(5) -0.2461(3) 0.1021(13) Uani 1 1 d . . . . .
N4 N -0.7573(4) -0.3081(4) -0.1861(3) 0.1003(13) Uani 1 1 d . . . . .
C7 C -0.2430(5) -0.1510(5) -0.2131(3) 0.0940(15) Uani 1 1 d . . . . .
H7 H -0.3109 -0.1169 -0.1942 0.113 Uiso 1 1 calc R . . . .
C8 C -0.8467(5) -0.8832(5) 0.0771(3) 0.0894(14) Uani 1 1 d . . . . .
C10 C -0.2778(5) -0.3778(6) -0.1838(3) 0.0985(16) Uani 1 1 d . . . . .
N11 N -0.8125(4) -0.4157(4) -0.1737(3) 0.1054(14) Uani 1 1 d . . . . .
H11 H -0.8491 -0.4562 -0.2073 0.126 Uiso 1 1 calc R . . . .
C13 C -0.7128(5) -0.2758(5) -0.1198(3) 0.0984(16) Uani 1 1 d . . . . .
C14 C -0.1523(5) -0.0890(5) -0.2466(3) 0.0957(15) Uani 1 1 d . . . . .
C15 C -0.9418(5) -0.9463(6) 0.0346(3) 0.0990(16) Uani 1 1 d . . . . .
C16 C -0.6835(6) -0.7976(6) 0.1153(4) 0.1096(18) Uani 1 1 d . . . . .
C17 C -0.7322(6) -0.8610(6) 0.0572(4) 0.1115(18) Uani 1 1 d . . . . .
H17 H -0.6959 -0.8840 0.0137 0.134 Uiso 1 1 calc R . . . .
C18 C -0.6421(6) -0.1652(6) -0.1119(4) 0.1122(19) Uani 1 1 d . . . . .
C21 C -0.8033(6) -0.4517(6) -0.1031(4) 0.117(2) Uani 1 1 d . . . . .
C23 C -0.6532(8) -0.0694(7) -0.1588(4) 0.134(2) Uani 1 1 d . . . . .
H23 H -0.7090 -0.0722 -0.1966 0.160 Uiso 1 1 calc R . . . .
C24 C -0.9147(7) -1.0368(7) -0.0148(4) 0.117(2) Uani 1 1 d . . . . .
H24 H -0.8365 -1.0560 -0.0228 0.140 Uiso 1 1 calc R . . . .
C25 C -0.1303(8) 0.0441(6) -0.2623(4) 0.131(2) Uani 1 1 d . . . . .
H25 H -0.1194 0.0495 -0.3157 0.157 Uiso 1 1 calc R . . . .
C28 C -1.0561(7) -0.9172(8) 0.0448(4) 0.131(2) Uani 1 1 d . . . . .
H28 H -1.0760 -0.8550 0.0771 0.157 Uiso 1 1 calc R . . . .
C29 C -0.7413(7) -0.3640(7) -0.0674(4) 0.120(2) Uani 1 1 d . . . . .
H29 H -0.7214 -0.3628 -0.0175 0.144 Uiso 1 1 calc R . . . .
C32 C -0.5801(13) 0.0356(9) -0.1508(7) 0.174(4) Uani 1 1 d . . . . .
H32 H -0.5872 0.1022 -0.1821 0.208 Uiso 1 1 calc R . . . .
C33 C -0.5637(7) -0.7416(9) 0.1272(5) 0.150(3) Uani 1 1 d . . . . .
H33 H -0.5649 -0.6929 0.1724 0.180 Uiso 1 1 calc R . . . .
C34 C -0.2212(7) -0.4838(7) -0.1683(4) 0.132(2) Uani 1 1 d . . . . .
H34 H -0.1411 -0.4898 -0.1765 0.158 Uiso 1 1 calc R . . . .
C35 C -0.4876(10) -0.0571(13) -0.0472(8) 0.180(4) Uani 1 1 d . . . . .
H35 H -0.4334 -0.0523 -0.0087 0.215 Uiso 1 1 calc R . . . .
C36 C -0.3964(7) -0.3733(7) -0.1725(5) 0.138(3) Uani 1 1 d . . . . .
H36 H -0.4375 -0.3027 -0.1843 0.166 Uiso 1 1 calc R . . . .
C38 C -0.8536(13) -0.5714(9) -0.0775(6) 0.177(4) Uani 1 1 d . . . . .
C40 C -0.4994(12) 0.0330(13) -0.0945(9) 0.179(5) Uani 1 1 d . . . . .
H40 H -0.4494 0.0993 -0.0893 0.215 Uiso 1 1 calc R . . . .
C42 C -1.1153(11) -1.0717(12) -0.0402(5) 0.173(4) Uani 1 1 d . . . . .
H42 H -1.1745 -1.1152 -0.0641 0.207 Uiso 1 1 calc R . . . .
C43 C -0.2821(11) -0.5835(8) -0.1404(6) 0.169(4) Uani 1 1 d . . . . .
H43 H -0.2423 -0.6550 -0.1289 0.203 Uiso 1 1 calc R . . . .
C44 C -0.4563(9) -0.4728(11) -0.1438(8) 0.185(5) Uani 1 1 d . . . . .
H44 H -0.5359 -0.4669 -0.1341 0.222 Uiso 1 1 calc R . . . .
C45 C -0.5574(7) -0.1592(9) -0.0560(6) 0.151(3) Uani 1 1 d . . . . .
H45 H -0.5476 -0.2248 -0.0241 0.181 Uiso 1 1 calc R . . . .
C46 C -0.8001(16) -0.6773(9) -0.1185(6) 0.227(7) Uani 1 1 d . . . . .
H46A H -0.7219 -0.6913 -0.1004 0.341 Uiso 0.59(3) 1 calc GR . P A 1
H46B H -0.7978 -0.6590 -0.1702 0.341 Uiso 0.59(3) 1 calc GR . P A 1
H46C H -0.8466 -0.7489 -0.1109 0.341 Uiso 0.59(3) 1 calc GR . P A 1
C48 C -1.1433(9) -0.9807(13) 0.0068(6) 0.183(4) Uani 1 1 d . . . . .
H48 H -1.2216 -0.9605 0.0137 0.220 Uiso 1 1 calc R . . . .
C49 C -0.0209(11) 0.0889(9) -0.2294(8) 0.209(5) Uani 1 1 d . . . . .
H49A H 0.0439 0.0441 -0.2490 0.314 Uiso 1 1 calc GR . . . .
H49B H -0.0230 0.0784 -0.1768 0.314 Uiso 1 1 calc GR . . . .
H49C H -0.0118 0.1736 -0.2407 0.314 Uiso 1 1 calc GR . . . .
C50 C -0.3996(12) -0.5758(10) -0.1302(6) 0.172(4) Uani 1 1 d . . . . .
H50 H -0.4406 -0.6433 -0.1136 0.206 Uiso 1 1 calc R . . . .
C51 C -0.2345(11) 0.1152(8) -0.2473(12) 0.271(9) Uani 1 1 d . . . . .
H51A H -0.2365 0.1352 -0.1958 0.407 Uiso 1 1 calc GR . . . .
H51B H -0.3029 0.0687 -0.2603 0.407 Uiso 1 1 calc GR . . . .
H51C H -0.2331 0.1886 -0.2759 0.407 Uiso 1 1 calc GR . . . .
C52 C -0.5362(12) -0.6585(18) 0.0625(10) 0.307(10) Uani 1 1 d . . . . .
H52A H -0.6016 -0.6055 0.0532 0.461 Uiso 1 1 calc GR . . . .
H52B H -0.5218 -0.7067 0.0194 0.461 Uiso 1 1 calc GR . . . .
H52C H -0.4680 -0.6108 0.0741 0.461 Uiso 1 1 calc GR . . . .
C54 C -0.4752(9) -0.8345(11) 0.1350(9) 0.222(6) Uani 1 1 d . . . . .
H54A H -0.4773 -0.8867 0.0926 0.333 Uiso 1 1 calc GR . . . .
H54B H -0.4900 -0.8815 0.1785 0.333 Uiso 1 1 calc GR . . . .
H54C H -0.3994 -0.7970 0.1391 0.333 Uiso 1 1 calc GR . . . .
C55 C -1.0010(11) -1.0997(9) -0.0527(4) 0.154(3) Uani 1 1 d . . . . .
H55 H -0.9814 -1.1602 -0.0862 0.184 Uiso 1 1 calc R . . . .
N5 N -0.9109(4) -0.5289(4) -0.3032(3) 0.1019(14) Uani 1 1 d . . . . .
C9 C -0.8876(5) -0.6290(5) -0.3426(3) 0.0961(16) Uani 1 1 d . . . . .
N19 N -1.0241(5) -0.5014(5) -0.3218(3) 0.1094(15) Uani 1 1 d . . . . .
H19 H -1.0612 -0.4399 -0.3044 0.131 Uiso 1 1 calc R . . . .
C20 C -0.7701(5) -0.6825(5) -0.3392(3) 0.0982(16) Uani 1 1 d . . . . .
C22 C -0.7534(6) -0.8006(6) -0.3599(4) 0.122(2) Uani 1 1 d . . . . .
H22 H -0.8173 -0.8468 -0.3754 0.147 Uiso 1 1 calc R . . . .
C26 C -1.0707(6) -0.5794(7) -0.3695(4) 0.117(2) Uani 1 1 d . . . . .
C27 C -0.9874(6) -0.6646(6) -0.3841(4) 0.1144(19) Uani 1 1 d . . . . .
H27 H -0.9946 -0.7319 -0.4149 0.137 Uiso 1 1 calc R . . . .
C30 C -0.5501(8) -0.7840(11) -0.3362(5) 0.150(3) Uani 1 1 d . . . . .
H30 H -0.4754 -0.8179 -0.3360 0.180 Uiso 1 1 calc R . . . .
C31 C -0.6741(6) -0.6175(8) -0.3154(5) 0.139(3) Uani 1 1 d . . . . .
H31 H -0.6838 -0.5378 -0.2995 0.167 Uiso 1 1 calc R . . . .
C37 C -0.5641(7) -0.6682(11) -0.3147(6) 0.162(3) Uani 1 1 d . . . . .
H37 H -0.4997 -0.6226 -0.2993 0.195 Uiso 1 1 calc R . . . .
C39 C -1.2133(11) -0.4352(13) -0.4259(8) 0.234(6) Uani 1 1 d . . . . .
H39A H -1.2206 -0.4360 -0.4787 0.351 Uiso 1 1 calc GR . . . .
H39B H -1.1473 -0.3861 -0.4117 0.351 Uiso 1 1 calc GR . . . .
H39C H -1.2833 -0.4020 -0.4051 0.351 Uiso 1 1 calc GR . . . .
C41 C -0.6431(9) -0.8525(9) -0.3582(5) 0.157(3) Uani 1 1 d . . . . .
H41 H -0.6326 -0.9332 -0.3720 0.188 Uiso 1 1 calc R . . . .
C47 C -1.2330(10) -0.6593(12) -0.4462(10) 0.249(8) Uani 1 1 d . . . . .
H47A H -1.2378 -0.7339 -0.4189 0.373 Uiso 1 1 calc GR . . . .
H47B H -1.1778 -0.6685 -0.4853 0.373 Uiso 1 1 calc GR . . . .
H47C H -1.3087 -0.6398 -0.4666 0.373 Uiso 1 1 calc GR . . . .
C53 C -1.1955(9) -0.5637(10) -0.3982(7) 0.173(4) Uani 1 1 d . . . . .
H53 H -1.2451 -0.5705 -0.3546 0.207 Uiso 1 1 calc R . . . .
N0AA N -0.8684(4) -0.8373(4) 0.1432(3) 0.0967(12) Uani 1 1 d . . . . .
N2 N -0.7666(5) -0.7857(5) 0.1644(3) 0.1024(14) Uani 1 1 d . . . . .
C1 C -0.879(3) -0.5752(12) -0.0022(12) 0.213(15) Uani 0.59(3) 1 d . . P A 1
H1A H -0.9185 -0.5015 0.0117 0.319 Uiso 0.59(3) 1 calc GR . P A 1
H1B H -0.8080 -0.5833 0.0259 0.319 Uiso 0.59(3) 1 calc GR . P A 1
H1C H -0.9294 -0.6434 0.0075 0.319 Uiso 0.59(3) 1 calc GR . P A 1
C56 C -0.950(3) -0.601(3) -0.090(3) 0.25(3) Uani 0.41(3) 1 d . . P A 2
H56 H -1.0312 -0.5950 -0.0888 0.297 Uiso 0.41(3) 1 calc R . P A 2
H1 H -0.017(5) -0.160(6) -0.292(4) 0.11(2) Uiso 1 1 d . . . . .
H2 H -0.748(5) -0.748(6) 0.207(4) 0.12(2) Uiso 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
N1 N3 1.342(7) . ?
N1 C14 1.338(7) . ?
C2 N3 1.337(7) . ?
C2 C7 1.389(8) . ?
C2 C10 1.465(8) . ?
N4 N11 1.361(6) . ?
N4 C13 1.348(7) . ?
C7 C14 1.385(8) . ?
C8 C15 1.495(8) . ?
C8 C17 1.381(8) . ?
C8 N0AA 1.326(7) . ?
C10 C34 1.360(9) . ?
C10 C36 1.372(9) . ?
N11 C21 1.343(8) . ?
C13 C18 1.466(9) . ?
C13 C29 1.399(9) . ?
C14 C25 1.513(9) . ?
C15 C24 1.376(9) . ?
C15 C28 1.358(9) . ?
C16 C17 1.376(9) . ?
C16 C33 1.512(10) . ?
C16 N2 1.314(8) . ?
C18 C23 1.358(10) . ?
C18 C45 1.395(11) . ?
C21 C29 1.356(9) . ?
C21 C38 1.511(11) . ?
C23 C32 1.432(14) . ?
C24 C55 1.381(11) . ?
C25 C49 1.463(12) . ?
C25 C51 1.451(12) . ?
C28 C48 1.393(12) . ?
C32 C40 1.368(16) . ?
C33 C52 1.523(17) . ?
C33 C54 1.442(13) . ?
C34 C43 1.397(11) . ?
C35 C40 1.316(16) . ?
C35 C45 1.385(13) . ?
C36 C44 1.394(13) . ?
C38 C46 1.514(16) . ?
C38 C1 1.40(2) . ?
C38 C56 1.17(3) . ?
C42 C48 1.355(16) . ?
C42 C55 1.362(14) . ?
C43 C50 1.359(13) . ?
C44 C50 1.327(14) . ?
C46 C56 1.97(4) . ?
N5 C9 1.340(7) . ?
N5 N19 1.365(6) . ?
C9 C20 1.465(8) . ?
C9 C27 1.413(8) . ?
N19 C26 1.326(8) . ?
C20 C22 1.366(8) . ?
C20 C31 1.373(9) . ?
C22 C41 1.383(10) . ?
C26 C27 1.363(9) . ?
C26 C53 1.520(11) . ?
C30 C37 1.342(13) . ?
C30 C41 1.357(12) . ?
C31 C37 1.374(11) . ?
C39 C53 1.513(16) . ?
C47 C53 1.428(15) . ?
N0AA N2 1.345(7) . ?

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
C14 N1 N3 114.3(5) . . ?
N3 C2 C7 109.8(5) . . ?
N3 C2 C10 120.6(5) . . ?
C7 C2 C10 129.6(5) . . ?
C2 N3 N1 104.6(5) . . ?
C13 N4 N11 104.6(5) . . ?
C14 C7 C2 107.2(5) . . ?
C17 C8 C15 129.0(6) . . ?
N0AA C8 C15 120.1(5) . . ?
N0AA C8 C17 110.9(5) . . ?
C34 C10 C2 120.5(6) . . ?
C34 C10 C36 117.9(7) . . ?
C36 C10 C2 121.6(6) . . ?
C21 N11 N4 112.5(5) . . ?
N4 C13 C18 120.4(5) . . ?
N4 C13 C29 109.6(5) . . ?
C29 C13 C18 129.9(6) . . ?
N1 C14 C7 104.0(5) . . ?
N1 C14 C25 122.8(6) . . ?
C7 C14 C25 133.2(6) . . ?
C24 C15 C8 120.3(6) . . ?
C28 C15 C8 120.8(6) . . ?
C28 C15 C24 118.9(6) . . ?
C17 C16 C33 132.2(7) . . ?
N2 C16 C17 106.3(6) . . ?
N2 C16 C33 121.4(7) . . ?
C16 C17 C8 105.3(5) . . ?
C23 C18 C13 122.4(7) . . ?
C23 C18 C45 118.6(7) . . ?
C45 C18 C13 119.1(7) . . ?
N11 C21 C29 106.3(6) . . ?
N11 C21 C38 121.6(7) . . ?
C29 C21 C38 132.1(7) . . ?
C18 C23 C32 120.8(10) . . ?
C15 C24 C55 121.4(8) . . ?
C49 C25 C14 113.0(7) . . ?
C51 C25 C14 110.4(7) . . ?
C51 C25 C49 116.1(10) . . ?
C15 C28 C48 119.7(9) . . ?
C21 C29 C13 107.0(6) . . ?
C40 C32 C23 116.5(10) . . ?
C16 C33 C52 109.2(8) . . ?
C54 C33 C16 110.9(8) . . ?
C54 C33 C52 110.6(10) . . ?
C10 C34 C43 120.7(7) . . ?
C40 C35 C45 118.8(13) . . ?
C10 C36 C44 121.0(8) . . ?
C21 C38 C46 111.3(9) . . ?
C1 C38 C21 114.2(11) . . ?
C1 C38 C46 123.1(11) . . ?
C56 C38 C21 123.0(18) . . ?
C56 C38 C46 94(3) . . ?
C35 C40 C32 124.4(12) . . ?
C48 C42 C55 120.3(10) . . ?
C50 C43 C34 119.8(9) . . ?
C50 C44 C36 120.0(9) . . ?
C35 C45 C18 120.9(11) . . ?
C38 C46 C56 36.2(13) . . ?
C42 C48 C28 120.6(10) . . ?
C44 C50 C43 120.5(9) . . ?
C42 C55 C24 118.9(10) . . ?
C9 N5 N19 104.1(5) . . ?
N5 C9 C20 119.6(6) . . ?
N5 C9 C27 110.4(5) . . ?
C27 C9 C20 130.0(5) . . ?
C26 N19 N5 112.9(5) . . ?
C22 C20 C9 120.0(6) . . ?
C22 C20 C31 117.9(6) . . ?
C31 C20 C9 122.0(6) . . ?
C20 C22 C41 121.0(7) . . ?
N19 C26 C27 107.2(5) . . ?
N19 C26 C53 121.1(6) . . ?
C27 C26 C53 131.7(7) . . ?
C26 C27 C9 105.4(6) . . ?
C37 C30 C41 121.1(8) . . ?
C20 C31 C37 121.1(8) . . ?
C30 C37 C31 119.6(9) . . ?
C30 C41 C22 119.1(8) . . ?
C39 C53 C26 110.0(9) . . ?
C47 C53 C26 113.5(8) . . ?
C47 C53 C39 116.5(11) . . ?
C8 N0AA N2 104.4(4) . . ?
C16 N2 N0AA 113.1(6) . . ?
C38 C56 C46 49.9(18) . . ?

_olex2_submission_special_instructions 'No special instructions were received'
