# Electronic Supplementary Material (ESI) for Organic Chemistry Frontiers.
# This journal is © the Partner Organisations 2022

####################################################################### 
# 
# 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_1_a
_database_code_depnum_ccdc_archive 'CCDC 2133551'
loop_
_audit_author_name
_audit_author_address
'Xiao-Qiang Hu'
;South Central University for Nationalities
China
;
_audit_update_record             
;
2022-01-10 deposited with the CCDC.	2022-03-07 downloaded from the CCDC.
;

# start Validation Reply Form
_vrf_PLAT026_1_a                 
;
PROBLEM: Ratio Observed / Unique Reflections (too) Low ..        37% Check 
RESPONSE: This is caused by the poor diffraction of the sample.
;
# end Validation Reply Form

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H14 N2 O'
_chemical_formula_weight         226.27

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           61
_space_group_name_H-M_alt        'P b c a'
_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'
'-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                   12.544(10)
_cell_length_b                   7.155(5)
_cell_length_c                   26.01(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2335(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1003
_cell_measurement_theta_min      3.13
_cell_measurement_theta_max      18.24

_exptl_crystal_description       Block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.287
_exptl_crystal_F_000             960
_exptl_transmission_factor_min   0.864
_exptl_transmission_factor_max   0.864
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.050
_exptl_absorpt_coefficient_mu    0.083
_shelx_estimated_absorpt_T_min   0.984
_shelx_estimated_absorpt_T_max   0.996
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14392
_diffrn_reflns_av_unetI/netI     0.1559
_diffrn_reflns_av_R_equivalents  0.1726
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         3.132
_diffrn_reflns_theta_max         24.996
_diffrn_reflns_theta_full        24.996
_diffrn_measured_fraction_theta_max 0.960
_diffrn_measured_fraction_theta_full 0.960
_diffrn_reflns_Laue_measured_fraction_max 0.960
_diffrn_reflns_Laue_measured_fraction_full 0.960
_diffrn_reflns_point_group_measured_fraction_max 0.960
_diffrn_reflns_point_group_measured_fraction_full 0.960
_reflns_number_total             1980
_reflns_number_gt                724
_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)+(0.1091P)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_number_reflns         1980
_refine_ls_number_parameters     144
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2580
_refine_ls_R_factor_gt           0.0892
_refine_ls_wR_factor_ref         0.2512
_refine_ls_wR_factor_gt          0.1962
_refine_ls_goodness_of_fit_ref   0.967
_refine_ls_restrained_S_all      0.967
_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 0.1764(3) 0.5525(5) 0.40905(17) 0.0639(16) Uani 1 1 d G . . . .
C2 C 0.1004(3) 0.5921(5) 0.4464(2) 0.091(2) Uani 1 1 d G . . . .
H2 H 0.0283 0.5853 0.4384 0.109 Uiso 1 1 calc R U . . .
C3 C 0.1322(4) 0.6419(5) 0.4957(2) 0.106(3) Uani 1 1 d G . . . .
H3 H 0.0814 0.6684 0.5207 0.127 Uiso 1 1 calc R U . . .
C4 C 0.2401(5) 0.6522(5) 0.50768(14) 0.091(2) Uani 1 1 d G . . . .
H4 H 0.2613 0.6855 0.5407 0.110 Uiso 1 1 calc R U . . .
C5 C 0.3161(3) 0.6126(5) 0.47035(18) 0.0694(17) Uani 1 1 d G . . . .
H5 H 0.3882 0.6194 0.4784 0.083 Uiso 1 1 calc R U . . .
C6 C 0.2842(3) 0.5627(5) 0.42104(16) 0.0573(15) Uani 1 1 d G . . . .
C7 C 0.3549(4) 0.5290(6) 0.3795(2) 0.0477(13) Uani 1 1 d . . . . .
C8 C 0.3103(4) 0.4882(6) 0.3330(2) 0.0585(15) Uani 1 1 d . . . . .
C9 C 0.3732(4) 0.4542(7) 0.2861(2) 0.0693(17) Uani 1 1 d . . . . .
H9A H 0.3328 0.4934 0.2562 0.083 Uiso 1 1 calc R U . . .
H9B H 0.3879 0.3216 0.2828 0.083 Uiso 1 1 calc R U . . .
C10 C 0.4766(4) 0.5612(8) 0.2885(2) 0.0762(18) Uani 1 1 d . . . . .
H10A H 0.5202 0.5276 0.2591 0.091 Uiso 1 1 calc R U . . .
H10B H 0.4615 0.6939 0.2863 0.091 Uiso 1 1 calc R U . . .
C11 C 0.5384(4) 0.5237(7) 0.3368(2) 0.0626(16) Uani 1 1 d . . . . .
C12 C 0.4725(4) 0.5333(7) 0.3837(3) 0.0633(15) Uani 1 1 d . . . . .
C13 C 0.6295(5) 0.6610(11) 0.3409(2) 0.120(3) Uani 1 1 d . . . . .
H13A H 0.6016 0.7855 0.3438 0.180 Uiso 1 1 calc R U . . .
H13B H 0.6732 0.6523 0.3107 0.180 Uiso 1 1 calc R U . . .
H13C H 0.6715 0.6324 0.3707 0.180 Uiso 1 1 calc R U . . .
C14 C 0.5821(5) 0.3230(9) 0.3345(2) 0.097(2) Uani 1 1 d . . . . .
H14A H 0.6202 0.2958 0.3656 0.146 Uiso 1 1 calc R U . . .
H14B H 0.6295 0.3112 0.3057 0.146 Uiso 1 1 calc R U . . .
H14C H 0.5241 0.2367 0.3307 0.146 Uiso 1 1 calc R U . . .
N1 N 0.1378(4) 0.5029(6) 0.3633(3) 0.0789(16) Uani 1 1 d . . . . .
N2 N 0.2030(4) 0.4711(6) 0.3250(2) 0.0722(14) Uani 1 1 d . . . . .
O1 O 0.5148(3) 0.5428(7) 0.42554(18) 0.1151(18) 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 1.334(6) . ?
C1 C2 1.3900 . ?
C1 C6 1.3900 . ?
C2 C3 1.3900 . ?
C2 H2 0.9300 . ?
C3 C4 1.3900 . ?
C3 H3 0.9300 . ?
C4 C5 1.3900 . ?
C4 H4 0.9300 . ?
C5 C6 1.3900 . ?
C5 H5 0.9300 . ?
C6 C7 1.419(6) . ?
C7 C8 1.363(7) . ?
C7 C12 1.480(7) . ?
C8 N2 1.368(7) . ?
C8 C9 1.474(7) . ?
C9 C10 1.508(7) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.500(7) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.475(7) . ?
C11 C13 1.511(7) . ?
C11 C14 1.539(7) . ?
C12 O1 1.213(6) . ?
C13 H13A 0.9600 . ?
C13 H13B 0.9600 . ?
C13 H13C 0.9600 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
N1 N2 1.308(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
N1 C1 C2 115.4(4) . . ?
N1 C1 C6 124.6(4) . . ?
C2 C1 C6 120.0 . . ?
C1 C2 C3 120.0 . . ?
C1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?
C4 C3 C2 120.0 . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C5 C4 C3 120.0 . . ?
C5 C4 H4 120.0 . . ?
C3 C4 H4 120.0 . . ?
C4 C5 C6 120.0 . . ?
C4 C5 H5 120.0 . . ?
C6 C5 H5 120.0 . . ?
C5 C6 C1 120.0 . . ?
C5 C6 C7 124.6(4) . . ?
C1 C6 C7 115.3(4) . . ?
C8 C7 C6 117.1(5) . . ?
C8 C7 C12 118.7(5) . . ?
C6 C7 C12 124.2(5) . . ?
C7 C8 N2 123.9(6) . . ?
C7 C8 C9 123.4(5) . . ?
N2 C8 C9 112.7(6) . . ?
C8 C9 C10 110.0(5) . . ?
C8 C9 H9A 109.7 . . ?
C10 C9 H9A 109.7 . . ?
C8 C9 H9B 109.7 . . ?
C10 C9 H9B 109.7 . . ?
H9A C9 H9B 108.2 . . ?
C11 C10 C9 112.9(4) . . ?
C11 C10 H10A 109.0 . . ?
C9 C10 H10A 109.0 . . ?
C11 C10 H10B 109.0 . . ?
C9 C10 H10B 109.0 . . ?
H10A C10 H10B 107.8 . . ?
C12 C11 C10 113.3(5) . . ?
C12 C11 C13 109.7(5) . . ?
C10 C11 C13 109.4(5) . . ?
C12 C11 C14 106.0(4) . . ?
C10 C11 C14 108.5(5) . . ?
C13 C11 C14 109.9(5) . . ?
O1 C12 C11 120.0(5) . . ?
O1 C12 C7 120.3(5) . . ?
C11 C12 C7 119.8(6) . . ?
C11 C13 H13A 109.5 . . ?
C11 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C11 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C11 C14 H14A 109.5 . . ?
C11 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C11 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N2 N1 C1 119.9(5) . . ?
N1 N2 C8 119.0(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
N1 C1 C2 C3 178.9(4) . . . . ?
C6 C1 C2 C3 0.0 . . . . ?
C1 C2 C3 C4 0.0 . . . . ?
C2 C3 C4 C5 0.0 . . . . ?
C3 C4 C5 C6 0.0 . . . . ?
C4 C5 C6 C1 0.0 . . . . ?
C4 C5 C6 C7 176.6(3) . . . . ?
N1 C1 C6 C5 -178.8(4) . . . . ?
C2 C1 C6 C5 0.0 . . . . ?
N1 C1 C6 C7 4.4(4) . . . . ?
C2 C1 C6 C7 -176.9(3) . . . . ?
C5 C6 C7 C8 -177.6(3) . . . . ?
C1 C6 C7 C8 -0.9(5) . . . . ?
C5 C6 C7 C12 3.1(6) . . . . ?
C1 C6 C7 C12 179.9(4) . . . . ?
C6 C7 C8 N2 -2.7(6) . . . . ?
C12 C7 C8 N2 176.6(4) . . . . ?
C6 C7 C8 C9 178.5(4) . . . . ?
C12 C7 C8 C9 -2.1(7) . . . . ?
C7 C8 C9 C10 -28.9(7) . . . . ?
N2 C8 C9 C10 152.2(4) . . . . ?
C8 C9 C10 C11 53.0(6) . . . . ?
C9 C10 C11 C12 -47.0(7) . . . . ?
C9 C10 C11 C13 -169.6(5) . . . . ?
C9 C10 C11 C14 70.5(6) . . . . ?
C10 C11 C12 O1 -165.4(5) . . . . ?
C13 C11 C12 O1 -42.9(8) . . . . ?
C14 C11 C12 O1 75.6(7) . . . . ?
C10 C11 C12 C7 15.3(7) . . . . ?
C13 C11 C12 C7 137.8(5) . . . . ?
C14 C11 C12 C7 -103.6(5) . . . . ?
C8 C7 C12 O1 -169.6(5) . . . . ?
C6 C7 C12 O1 9.7(8) . . . . ?
C8 C7 C12 C11 9.7(7) . . . . ?
C6 C7 C12 C11 -171.0(4) . . . . ?
C2 C1 N1 N2 176.9(3) . . . . ?
C6 C1 N1 N2 -4.3(6) . . . . ?
C1 N1 N2 C8 0.5(7) . . . . ?
C7 C8 N2 N1 3.0(7) . . . . ?
C9 C8 N2 N1 -178.1(4) . . . . ?

_refine_diff_density_max         0.165
_refine_diff_density_min         -0.185
_refine_diff_density_rms         0.051

####################################################################### 
# 
# 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_1
_database_code_depnum_ccdc_archive 'CCDC 2133553'
loop_
_audit_author_name
_audit_author_address
'Xiao-Qiang Hu'
;South Central University for Nationalities
China
;
_audit_update_record             
;
2022-01-10 deposited with the CCDC.	2022-03-07 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         ?
_chemical_formula_sum            'C12 H10 N2 O'
_chemical_formula_weight         198.22

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           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                   10.846(3)
_cell_length_b                   12.737(4)
_cell_length_c                   14.174(4)
_cell_angle_alpha                90
_cell_angle_beta                 96.552(6)
_cell_angle_gamma                90
_cell_volume                     1945.1(10)
_cell_formula_units_Z            8
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    1688
_cell_measurement_theta_min      2.48
_cell_measurement_theta_max      19.74

_exptl_crystal_description       Block
_exptl_crystal_colour            orange
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.354
_exptl_crystal_F_000             832
_exptl_transmission_factor_min   0.864
_exptl_transmission_factor_max   0.864
_exptl_crystal_size_max          0.200
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.089
_shelx_estimated_absorpt_T_min   0.982
_shelx_estimated_absorpt_T_max   0.982
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  CCD
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            19868
_diffrn_reflns_av_unetI/netI     0.1190
_diffrn_reflns_av_R_equivalents  0.1273
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.156
_diffrn_reflns_theta_max         25.000
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measured_fraction_theta_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.990
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.990
_diffrn_reflns_point_group_measured_fraction_full 0.990
_reflns_number_total             3382
_reflns_number_gt                1489
_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)+(0.1228P)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_number_reflns         3382
_refine_ls_number_parameters     271
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.2475
_refine_ls_R_factor_gt           0.1109
_refine_ls_wR_factor_ref         0.2903
_refine_ls_wR_factor_gt          0.2353
_refine_ls_goodness_of_fit_ref   1.178
_refine_ls_restrained_S_all      1.178
_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 0.9242(5) 0.8500(4) 0.5643(4) 0.0705(14) Uani 1 1 d . U . . .
C2 C 0.9627(5) 0.8888(6) 0.6544(4) 0.0858(18) Uani 1 1 d . . . . .
H2 H 1.0085 0.8463 0.6989 0.103 Uiso 1 1 calc R U . . .
C3 C 0.9338(6) 0.9880(6) 0.6780(4) 0.0931(19) Uani 1 1 d . . . . .
H3 H 0.9584 1.0135 0.7387 0.112 Uiso 1 1 calc R U . . .
C4 C 0.8666(5) 1.0521(5) 0.6102(4) 0.0802(16) Uani 1 1 d . . . . .
H4 H 0.8489 1.1208 0.6261 0.096 Uiso 1 1 calc R U . . .
C5 C 0.8265(5) 1.0159(4) 0.5211(4) 0.0719(15) Uani 1 1 d . . . . .
H5 H 0.7817 1.0600 0.4775 0.086 Uiso 1 1 calc R U . . .
C6 C 0.8527(4) 0.9131(4) 0.4955(3) 0.0602(13) Uani 1 1 d . . . . .
C7 C 0.8156(4) 0.8650(4) 0.4067(3) 0.0596(13) Uani 1 1 d . . . . .
C8 C 0.8557(5) 0.7632(4) 0.3928(4) 0.0728(15) Uani 1 1 d . . . . .
C9 C 0.8246(6) 0.7076(4) 0.3005(4) 0.0918(18) Uani 1 1 d . . . . .
H9A H 0.8935 0.6624 0.2894 0.110 Uiso 1 1 calc R U . . .
H9B H 0.7527 0.6633 0.3049 0.110 Uiso 1 1 calc R U . . .
C10 C 0.7983(7) 0.7788(5) 0.2192(4) 0.106(2) Uani 1 1 d . . . . .
H10A H 0.7646 0.7386 0.1641 0.128 Uiso 1 1 calc R U . . .
H10B H 0.8753 0.8106 0.2048 0.128 Uiso 1 1 calc R U . . .
C11 C 0.7101(6) 0.8623(4) 0.2370(4) 0.0891(18) Uani 1 1 d . . . . .
H11A H 0.7106 0.9145 0.1872 0.107 Uiso 1 1 calc R U . . .
H11B H 0.6275 0.8320 0.2318 0.107 Uiso 1 1 calc R U . . .
C12 C 0.7334(5) 0.9163(4) 0.3298(3) 0.0682(15) Uani 1 1 d . . . . .
C13 C 0.7033(5) 0.5122(4) 0.5154(3) 0.0670(14) Uani 1 1 d . U . . .
C14 C 0.7822(5) 0.4160(4) 0.5366(4) 0.0913(18) Uani 1 1 d . . . . .
H14A H 0.7360 0.3544 0.5129 0.110 Uiso 1 1 calc R U . . .
H14B H 0.8556 0.4210 0.5037 0.110 Uiso 1 1 calc R U . . .
C15 C 0.8204(6) 0.4033(5) 0.6399(4) 0.102(2) Uani 1 1 d . . . . .
H15A H 0.8809 0.3472 0.6505 0.122 Uiso 1 1 calc R U . . .
H15B H 0.7490 0.3853 0.6721 0.122 Uiso 1 1 calc R U . . .
C16 C 0.8762(6) 0.5049(6) 0.6789(4) 0.111(2) Uani 1 1 d . . . . .
H16A H 0.9491 0.5208 0.6477 0.133 Uiso 1 1 calc R U . . .
H16B H 0.9026 0.4964 0.7462 0.133 Uiso 1 1 calc R U . . .
C17 C 0.7882(6) 0.5944(5) 0.6653(4) 0.0814(17) Uani 1 1 d . . . . .
C18 C 0.7028(4) 0.5969(4) 0.5753(3) 0.0577(12) Uani 1 1 d . U . . .
C19 C 0.6246(4) 0.6829(4) 0.5487(3) 0.0612(13) Uani 1 1 d . . . . .
C20 C 0.5553(5) 0.6762(4) 0.4589(4) 0.0720(15) Uani 1 1 d . U . . .
C21 C 0.4785(5) 0.7603(5) 0.4220(4) 0.0887(18) Uani 1 1 d . . . . .
H21 H 0.4350 0.7562 0.3617 0.106 Uiso 1 1 calc R U . . .
C22 C 0.4702(6) 0.8457(6) 0.4759(6) 0.100(2) Uani 1 1 d . . . . .
H22 H 0.4197 0.9011 0.4525 0.120 Uiso 1 1 calc R U . . .
C23 C 0.5342(7) 0.8535(5) 0.5644(6) 0.102(2) Uani 1 1 d . . . . .
H23 H 0.5251 0.9138 0.5999 0.122 Uiso 1 1 calc R U . . .
C24 C 0.6117(5) 0.7748(5) 0.6030(4) 0.0830(17) Uani 1 1 d . . . . .
H24 H 0.6546 0.7820 0.6633 0.100 Uiso 1 1 calc R U . . .
N1 N 0.9572(4) 0.7493(4) 0.5453(4) 0.0925(15) Uani 1 1 d . U . . .
N2 N 0.9263(4) 0.7064(4) 0.4603(4) 0.0898(15) Uani 1 1 d . . . . .
N3 N 0.6324(5) 0.5061(4) 0.4311(3) 0.0823(14) Uani 1 1 d . . . . .
N4 N 0.5615(5) 0.5889(4) 0.4029(3) 0.0951(16) Uani 1 1 d . U . . .
O1 O 0.6809(4) 0.9976(3) 0.3432(3) 0.1033(14) Uani 1 1 d . . . . .
O2 O 0.7863(4) 0.6649(4) 0.7254(3) 0.1152(16) 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 1.367(7) . ?
C1 C2 1.388(7) . ?
C1 C6 1.424(7) . ?
C2 C3 1.353(8) . ?
C2 H2 0.9300 . ?
C3 C4 1.400(8) . ?
C3 H3 0.9300 . ?
C4 C5 1.366(7) . ?
C4 H4 0.9300 . ?
C5 C6 1.397(6) . ?
C5 H5 0.9300 . ?
C6 C7 1.416(6) . ?
C7 C8 1.388(7) . ?
C7 C12 1.479(7) . ?
C8 N2 1.363(6) . ?
C8 C9 1.492(7) . ?
C9 C10 1.469(7) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.470(7) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.482(7) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 O1 1.207(6) . ?
C13 N3 1.347(6) . ?
C13 C18 1.373(6) . ?
C13 C14 1.505(7) . ?
C14 C15 1.485(7) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.506(8) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 C17 1.485(8) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 O2 1.240(6) . ?
C17 C18 1.489(7) . ?
C18 C19 1.410(6) . ?
C19 C20 1.405(7) . ?
C19 C24 1.417(7) . ?
C20 N4 1.372(6) . ?
C20 C21 1.420(7) . ?
C21 C22 1.338(8) . ?
C21 H21 0.9300 . ?
C22 C23 1.367(9) . ?
C22 H22 0.9300 . ?
C23 C24 1.380(8) . ?
C23 H23 0.9300 . ?
C24 H24 0.9300 . ?
N1 N2 1.330(6) . ?
N3 N4 1.340(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
N1 C1 C2 117.2(5) . . ?
N1 C1 C6 121.9(5) . . ?
C2 C1 C6 120.9(5) . . ?
C3 C2 C1 120.4(6) . . ?
C3 C2 H2 119.8 . . ?
C1 C2 H2 119.8 . . ?
C2 C3 C4 119.5(6) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 H3 120.3 . . ?
C5 C4 C3 121.6(6) . . ?
C5 C4 H4 119.2 . . ?
C3 C4 H4 119.2 . . ?
C4 C5 C6 120.2(5) . . ?
C4 C5 H5 119.9 . . ?
C6 C5 H5 119.9 . . ?
C5 C6 C7 126.3(5) . . ?
C5 C6 C1 117.5(5) . . ?
C7 C6 C1 116.2(5) . . ?
C8 C7 C6 118.0(4) . . ?
C8 C7 C12 118.7(5) . . ?
C6 C7 C12 123.3(5) . . ?
N2 C8 C7 123.8(5) . . ?
N2 C8 C9 114.6(5) . . ?
C7 C8 C9 121.7(5) . . ?
C10 C9 C8 113.5(5) . . ?
C10 C9 H9A 108.9 . . ?
C8 C9 H9A 108.9 . . ?
C10 C9 H9B 108.9 . . ?
C8 C9 H9B 108.9 . . ?
H9A C9 H9B 107.7 . . ?
C9 C10 C11 112.6(5) . . ?
C9 C10 H10A 109.1 . . ?
C11 C10 H10A 109.1 . . ?
C9 C10 H10B 109.1 . . ?
C11 C10 H10B 109.1 . . ?
H10A C10 H10B 107.8 . . ?
C12 C11 C10 116.1(5) . . ?
C12 C11 H11A 108.3 . . ?
C10 C11 H11A 108.3 . . ?
C12 C11 H11B 108.3 . . ?
C10 C11 H11B 108.3 . . ?
H11A C11 H11B 107.4 . . ?
O1 C12 C11 120.1(5) . . ?
O1 C12 C7 121.3(5) . . ?
C11 C12 C7 118.5(5) . . ?
N3 C13 C18 123.5(5) . . ?
N3 C13 C14 112.6(5) . . ?
C18 C13 C14 123.9(5) . . ?
C15 C14 C13 112.0(5) . . ?
C15 C14 H14A 109.2 . . ?
C13 C14 H14A 109.2 . . ?
C15 C14 H14B 109.2 . . ?
C13 C14 H14B 109.2 . . ?
H14A C14 H14B 107.9 . . ?
C14 C15 C16 108.9(5) . . ?
C14 C15 H15A 109.9 . . ?
C16 C15 H15A 109.9 . . ?
C14 C15 H15B 109.9 . . ?
C16 C15 H15B 109.9 . . ?
H15A C15 H15B 108.3 . . ?
C15 C16 C17 112.8(5) . . ?
C15 C16 H16A 109.0 . . ?
C17 C16 H16A 109.0 . . ?
C15 C16 H16B 109.0 . . ?
C17 C16 H16B 109.0 . . ?
H16A C16 H16B 107.8 . . ?
O2 C17 C18 121.1(6) . . ?
O2 C17 C16 121.9(6) . . ?
C18 C17 C16 117.1(5) . . ?
C13 C18 C19 119.3(4) . . ?
C13 C18 C17 117.9(5) . . ?
C19 C18 C17 122.8(5) . . ?
C20 C19 C18 116.0(5) . . ?
C20 C19 C24 117.8(5) . . ?
C18 C19 C24 126.2(5) . . ?
N4 C20 C19 121.1(5) . . ?
N4 C20 C21 117.7(5) . . ?
C19 C20 C21 121.2(5) . . ?
C22 C21 C20 118.6(6) . . ?
C22 C21 H21 120.7 . . ?
C20 C21 H21 120.7 . . ?
C21 C22 C23 121.5(6) . . ?
C21 C22 H22 119.3 . . ?
C23 C22 H22 119.3 . . ?
C24 C23 C22 122.3(6) . . ?
C24 C23 H23 118.9 . . ?
C22 C23 H23 118.9 . . ?
C23 C24 C19 118.6(6) . . ?
C23 C24 H24 120.7 . . ?
C19 C24 H24 120.7 . . ?
N2 N1 C1 121.3(5) . . ?
N1 N2 C8 118.7(5) . . ?
N4 N3 C13 118.0(4) . . ?
N3 N4 C20 122.0(4) . . ?

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
N1 C1 C2 C3 179.7(5) . . . . ?
C6 C1 C2 C3 -0.8(8) . . . . ?
C1 C2 C3 C4 -1.1(9) . . . . ?
C2 C3 C4 C5 1.7(8) . . . . ?
C3 C4 C5 C6 -0.3(8) . . . . ?
C4 C5 C6 C7 179.0(5) . . . . ?
C4 C5 C6 C1 -1.5(7) . . . . ?
N1 C1 C6 C5 -178.4(5) . . . . ?
C2 C1 C6 C5 2.1(7) . . . . ?
N1 C1 C6 C7 1.1(7) . . . . ?
C2 C1 C6 C7 -178.4(4) . . . . ?
C5 C6 C7 C8 176.9(5) . . . . ?
C1 C6 C7 C8 -2.6(6) . . . . ?
C5 C6 C7 C12 -5.1(7) . . . . ?
C1 C6 C7 C12 175.3(4) . . . . ?
C6 C7 C8 N2 1.5(7) . . . . ?
C12 C7 C8 N2 -176.5(5) . . . . ?
C6 C7 C8 C9 -178.0(5) . . . . ?
C12 C7 C8 C9 3.9(7) . . . . ?
N2 C8 C9 C10 -155.1(5) . . . . ?
C7 C8 C9 C10 24.5(8) . . . . ?
C8 C9 C10 C11 -48.6(8) . . . . ?
C9 C10 C11 C12 45.9(8) . . . . ?
C10 C11 C12 O1 166.0(5) . . . . ?
C10 C11 C12 C7 -17.8(7) . . . . ?
C8 C7 C12 O1 168.6(5) . . . . ?
C6 C7 C12 O1 -9.3(8) . . . . ?
C8 C7 C12 C11 -7.5(7) . . . . ?
C6 C7 C12 C11 174.5(5) . . . . ?
N3 C13 C14 C15 -157.6(5) . . . . ?
C18 C13 C14 C15 22.1(7) . . . . ?
C13 C14 C15 C16 -51.1(7) . . . . ?
C14 C15 C16 C17 59.8(7) . . . . ?
C15 C16 C17 O2 143.9(6) . . . . ?
C15 C16 C17 C18 -36.9(7) . . . . ?
N3 C13 C18 C19 0.1(7) . . . . ?
C14 C13 C18 C19 -179.6(4) . . . . ?
N3 C13 C18 C17 -178.5(4) . . . . ?
C14 C13 C18 C17 1.8(7) . . . . ?
O2 C17 C18 C13 -175.0(5) . . . . ?
C16 C17 C18 C13 5.8(7) . . . . ?
O2 C17 C18 C19 6.5(7) . . . . ?
C16 C17 C18 C19 -172.7(5) . . . . ?
C13 C18 C19 C20 -2.4(6) . . . . ?
C17 C18 C19 C20 176.1(4) . . . . ?
C13 C18 C19 C24 178.7(5) . . . . ?
C17 C18 C19 C24 -2.8(7) . . . . ?
C18 C19 C20 N4 2.1(7) . . . . ?
C24 C19 C20 N4 -179.0(5) . . . . ?
C18 C19 C20 C21 -176.5(5) . . . . ?
C24 C19 C20 C21 2.5(7) . . . . ?
N4 C20 C21 C22 179.3(5) . . . . ?
C19 C20 C21 C22 -2.1(8) . . . . ?
C20 C21 C22 C23 0.4(9) . . . . ?
C21 C22 C23 C24 0.7(10) . . . . ?
C22 C23 C24 C19 -0.2(9) . . . . ?
C20 C19 C24 C23 -1.3(7) . . . . ?
C18 C19 C24 C23 177.5(5) . . . . ?
C2 C1 N1 N2 -178.8(5) . . . . ?
C6 C1 N1 N2 1.7(8) . . . . ?
C1 N1 N2 C8 -2.9(8) . . . . ?
C7 C8 N2 N1 1.3(8) . . . . ?
C9 C8 N2 N1 -179.1(5) . . . . ?
C18 C13 N3 N4 2.7(7) . . . . ?
C14 C13 N3 N4 -177.6(5) . . . . ?
C13 N3 N4 C20 -3.1(8) . . . . ?
C19 C20 N4 N3 0.7(8) . . . . ?
C21 C20 N4 N3 179.3(5) . . . . ?

_refine_diff_density_max         0.386
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.050

