# Electronic Supplementary Material (ESI) for Molecular Systems Design & Engineering.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_CP_1
_audit_block_doi                 10.5517/ccdc.csd.cc2d6j05
_database_code_depnum_ccdc_archive 'CCDC 2210796'
loop_
_audit_author_name
_audit_author_address
'Jian Luan'
;Northeastern University
China
;
_audit_update_record             
;
2023-05-19 deposited with the CCDC.	2023-07-27 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            'C18 H22 Cl Cu N4 O3'
_chemical_formula_weight         441.38

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'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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'

_cell_length_a                   9.2920(5)
_cell_length_b                   10.0946(5)
_cell_length_c                   12.2235(6)
_cell_angle_alpha                112.9440(10)
_cell_angle_beta                 99.3390(10)
_cell_angle_gamma                105.5580(10)
_cell_volume                     970.06(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    2331
_cell_measurement_theta_min      1.897
_cell_measurement_theta_max      28.425

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            YELLOW
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.511
_exptl_crystal_F_000             456
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.21
_exptl_absorpt_coefficient_mu    1.290
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.732
_exptl_absorpt_correction_T_max  0.763
_exptl_absorpt_process_details   SADABS
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            7322
_diffrn_reflns_av_unetI/netI     0.0349
_diffrn_reflns_av_R_equivalents  0.0157
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         1.897
_diffrn_reflns_theta_max         28.425
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             4851
_reflns_number_gt                3579
_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       'Bruker Instrument Service vV6.2.9'
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'DIAMOND, Vers. 3.2h (Brandenburg, 2012)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0407P)²+0.3526P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4851
_refine_ls_number_parameters     244
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0594
_refine_ls_R_factor_gt           0.0392
_refine_ls_wR_factor_ref         0.0991
_refine_ls_wR_factor_gt          0.0909
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_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
Cu1 Cu 0.14336(4) 0.07416(4) -0.02549(3) 0.05271(12) Uani 1 1 d . . . . .
O1 O 0.06487(19) -0.30102(17) -0.50754(14) 0.0399(4) Uani 1 1 d . . . . .
N1 N 0.1532(2) 0.0939(2) -0.18345(15) 0.0373(4) Uani 1 1 d . . . . .
C1 C 0.1743(3) 0.2247(3) -0.1930(2) 0.0409(5) Uani 1 1 d . . . . .
H1A H 0.178806 0.311302 -0.124464 0.049 Uiso 1 1 calc R U . . .
O1W O -0.1829(2) -0.3664(2) -0.4082(2) 0.0704(6) Uani 1 1 d . . . . .
H1WA H -0.106704 -0.345988 -0.436693 0.084 Uiso 1 1 d R U . . .
H1WB H -0.134754 -0.329248 -0.331313 0.084 Uiso 1 1 d R U . . .
Cl1 Cl -0.00567(8) 0.19756(7) 0.09097(6) 0.05024(17) Uani 1 1 d . . . . .
N2 N 0.3605(2) 0.1529(2) 0.09778(16) 0.0376(4) Uani 1 1 d . . . . .
O2 O 0.5977(2) -0.10223(19) -0.41608(14) 0.0563(5) Uani 1 1 d . . . . .
C2 C 0.1897(3) 0.2386(3) -0.2982(2) 0.0398(5) Uani 1 1 d . . . . .
H2A H 0.204159 0.332286 -0.300271 0.048 Uiso 1 1 calc R U . . .
N3 N 0.2147(2) -0.16416(19) -0.58399(15) 0.0299(4) Uani 1 1 d . . . . .
H3B H 0.258751 -0.073712 -0.577472 0.036 Uiso 1 1 calc R U . . .
C3 C 0.1833(3) 0.1108(2) -0.40134(19) 0.0337(5) Uani 1 1 d . . . . .
H3A H 0.195033 0.117598 -0.473328 0.040 Uiso 1 1 calc R U . . .
N4 N 0.3968(2) -0.32950(19) -0.53142(15) 0.0308(4) Uani 1 1 d . . . . .
H4A H 0.338704 -0.412694 -0.532815 0.037 Uiso 1 1 calc R U . . .
C4 C 0.1589(2) -0.0271(2) -0.39478(17) 0.0279(4) Uani 1 1 d . . . . .
C5 C 0.1449(3) -0.0296(3) -0.28428(18) 0.0336(5) Uani 1 1 d . . . . .
H5A H 0.128936 -0.122124 -0.279825 0.040 Uiso 1 1 calc R U . . .
C6 C 0.1418(2) -0.1764(2) -0.50108(18) 0.0287(4) Uani 1 1 d . . . . .
C7 C 0.2236(2) -0.2970(2) -0.68554(17) 0.0278(4) Uani 1 1 d . . . . .
H7A H 0.137536 -0.390350 -0.702409 0.033 Uiso 1 1 calc R U . . .
C8 C 0.2092(3) -0.2765(3) -0.80364(18) 0.0364(5) Uani 1 1 d . . . . .
H8A H 0.108127 -0.269916 -0.829810 0.044 Uiso 1 1 calc R U . . .
H8B H 0.289869 -0.180800 -0.786255 0.044 Uiso 1 1 calc R U . . .
C9 C 0.2255(3) -0.4110(3) -0.90821(19) 0.0394(5) Uani 1 1 d . . . . .
H9A H 0.138759 -0.505320 -0.931165 0.047 Uiso 1 1 calc R U . . .
H9B H 0.221146 -0.392813 -0.980731 0.047 Uiso 1 1 calc R U . . .
C10 C 0.3786(3) -0.4307(3) -0.8688(2) 0.0429(6) Uani 1 1 d . . . . .
H10A H 0.465438 -0.340451 -0.853746 0.052 Uiso 1 1 calc R U . . .
H10B H 0.383553 -0.520031 -0.935443 0.052 Uiso 1 1 calc R U . . .
C11 C 0.3935(3) -0.4516(3) -0.75130(19) 0.0370(5) Uani 1 1 d . . . . .
H11A H 0.493962 -0.459617 -0.725905 0.044 Uiso 1 1 calc R U . . .
H11B H 0.311826 -0.546458 -0.768182 0.044 Uiso 1 1 calc R U . . .
C12 C 0.3796(2) -0.3153(2) -0.64661(17) 0.0282(4) Uani 1 1 d . . . . .
H12A H 0.464295 -0.221458 -0.630569 0.034 Uiso 1 1 calc R U . . .
C13 C 0.4994(2) -0.2178(2) -0.42459(18) 0.0305(4) Uani 1 1 d . . . . .
C14 C 0.4969(3) 0.2122(3) 0.0786(2) 0.0446(6) Uani 1 1 d . . . . .
H14A H 0.494424 0.204731 0.000009 0.054 Uiso 1 1 calc R U . . .
C15 C 0.6387(3) 0.2829(3) 0.1688(2) 0.0466(6) Uani 1 1 d . . . . .
H15A H 0.729623 0.322126 0.151069 0.056 Uiso 1 1 calc R U . . .
C16 C 0.6459(3) 0.2957(3) 0.2869(2) 0.0383(5) Uani 1 1 d . . . . .
H16A H 0.740482 0.346364 0.350422 0.046 Uiso 1 1 calc R U . . .
C17 C 0.5078(2) 0.2307(2) 0.30733(18) 0.0295(4) Uani 1 1 d . . . . .
C18 C 0.3699(3) 0.1609(2) 0.21123(19) 0.0345(5) Uani 1 1 d . . . . .
H18A H 0.278040 0.116824 0.225731 0.041 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
Cu1 N1 2.0307(18) . ?
Cu1 N2 2.0476(19) . ?
Cu1 Cl1 2.3829(7) . ?
Cu1 Cl1 2.4237(7) 2 ?
Cu1 Cu1 2.9756(6) 2 ?
O1 C6 1.234(2) . ?
N1 C1 1.336(3) . ?
N1 C5 1.342(3) . ?
C1 C2 1.372(3) . ?
N2 C18 1.344(3) . ?
N2 C14 1.348(3) . ?
O2 C13 1.229(2) . ?
C2 C3 1.387(3) . ?
N3 C6 1.333(2) . ?
N3 C7 1.463(2) . ?
C3 C4 1.386(3) . ?
N4 C13 1.325(3) . ?
N4 C12 1.458(2) . ?
C4 C5 1.387(3) . ?
C4 C6 1.504(3) . ?
C7 C8 1.526(3) . ?
C7 C12 1.533(3) . ?
C8 C9 1.524(3) . ?
C9 C10 1.516(3) . ?
C10 C11 1.521(3) . ?
C11 C12 1.524(3) . ?
C13 C17 1.499(3) 2_655 ?
C14 C15 1.368(3) . ?
C15 C16 1.387(3) . ?
C16 C17 1.385(3) . ?
C17 C18 1.379(3) . ?

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 Cu1 N2 112.68(7) . . ?
N1 Cu1 Cl1 117.18(6) . . ?
N2 Cu1 Cl1 105.92(5) . . ?
N1 Cu1 Cl1 106.21(6) . 2 ?
N2 Cu1 Cl1 110.98(6) . 2 ?
Cl1 Cu1 Cl1 103.51(2) . 2 ?
N1 Cu1 Cu1 126.39(6) . 2 ?
N2 Cu1 Cu1 120.75(5) . 2 ?
Cl1 Cu1 Cu1 52.373(18) . 2 ?
Cl1 Cu1 Cu1 51.139(17) 2 2 ?
C1 N1 C5 116.87(18) . . ?
C1 N1 Cu1 124.33(14) . . ?
C5 N1 Cu1 118.74(15) . . ?
N1 C1 C2 123.7(2) . . ?
Cu1 Cl1 Cu1 76.49(2) . 2 ?
C18 N2 C14 116.39(19) . . ?
C18 N2 Cu1 118.54(15) . . ?
C14 N2 Cu1 124.75(15) . . ?
C1 C2 C3 119.0(2) . . ?
C6 N3 C7 123.23(17) . . ?
C4 C3 C2 118.53(19) . . ?
C13 N4 C12 121.87(16) . . ?
C3 C4 C5 118.18(18) . . ?
C3 C4 C6 124.33(17) . . ?
C5 C4 C6 117.46(18) . . ?
N1 C5 C4 123.7(2) . . ?
O1 C6 N3 123.59(18) . . ?
O1 C6 C4 120.19(17) . . ?
N3 C6 C4 116.22(17) . . ?
N3 C7 C8 110.66(16) . . ?
N3 C7 C12 109.45(16) . . ?
C8 C7 C12 109.97(16) . . ?
C9 C8 C7 110.99(18) . . ?
C10 C9 C8 111.19(18) . . ?
C9 C10 C11 110.99(18) . . ?
C10 C11 C12 110.40(18) . . ?
N4 C12 C11 112.03(17) . . ?
N4 C12 C7 110.31(16) . . ?
C11 C12 C7 110.73(16) . . ?
O2 C13 N4 123.48(18) . . ?
O2 C13 C17 118.15(18) . 2_655 ?
N4 C13 C17 118.34(17) . 2_655 ?
N2 C14 C15 123.4(2) . . ?
C14 C15 C16 119.5(2) . . ?
C17 C16 C15 118.0(2) . . ?
C18 C17 C16 118.82(18) . . ?
C18 C17 C13 117.17(18) . 2_655 ?
C16 C17 C13 123.74(19) . 2_655 ?
N2 C18 C17 123.79(19) . . ?

_refine_diff_density_max         0.351
_refine_diff_density_min         -0.342
_refine_diff_density_rms         0.054



####################################################################### 
# 
# 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_CP_2
_audit_block_doi                 10.5517/ccdc.csd.cc2d6j16
_database_code_depnum_ccdc_archive 'CCDC 2210797'
loop_
_audit_author_name
_audit_author_address
'Jian Luan'
;Northeastern University
China
;
_audit_update_record             
;
2023-06-10 deposited with the CCDC.	2023-07-27 downloaded from the CCDC.
;
_audit_creation_date             2023-06-08
_audit_creation_method           
;
Olex2 1.5
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2019/2
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H20 Cu N5 O5'
_chemical_formula_sum            'C18 H20 Cu N5 O5'
_chemical_formula_weight         449.93
_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 0.0033 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'
Cu Cu 0.3201 1.2651 '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'

_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      orthorhombic
_space_group_IT_number           54
_space_group_name_H-M_alt        'P c c a'
_space_group_name_Hall           '-P 2a 2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z'
'-x, y, -z+1/2'
'x+1/2, -y, -z+1/2'
'-x, -y, -z'
'x-1/2, y, -z'
'x, -y, z-1/2'
'-x-1/2, y, z-1/2'

_cell_length_a                   12.4624(12)
_cell_length_b                   5.0727(5)
_cell_length_c                   29.121(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1841.0(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2858
_cell_measurement_temperature    300.00
_cell_measurement_theta_max      26.252
_cell_measurement_theta_min      2.798
_shelx_estimated_absorpt_T_max   0.887
_shelx_estimated_absorpt_T_min   0.856
_exptl_absorpt_coefficient_mu    1.230
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_correction_T_min  0.6667
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.623
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             928
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.12
_exptl_crystal_size_min          0.1
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0353
_diffrn_reflns_av_unetI/netI     0.0224
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -37
_diffrn_reflns_number            11483
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.197
_diffrn_reflns_theta_min         2.151
_diffrn_ambient_temperature      300.00
_diffrn_detector                 'CCD area detector'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_current           30.0
_diffrn_source_power             1.2
_diffrn_source_target            Mo
_diffrn_source_voltage           40.0
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1683
_reflns_number_total             2067
_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       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       'Bruker D8 Venture diffractrometer'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2019/2 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.404
_refine_diff_density_min         -0.366
_refine_diff_density_rms         0.057
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     147
_refine_ls_number_reflns         2067
_refine_ls_number_restraints     35
_refine_ls_R_factor_all          0.0455
_refine_ls_R_factor_gt           0.0347
_refine_ls_restrained_S_all      1.030
_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)+(0.0521P)²+1.0983P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0930
_refine_ls_wR_factor_ref         0.0983
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Restrained distances
 O2A-N3 \\sim O2-N3
 with sigma of 0.02
 Cu1-O2 \\sim Cu1-O2A
 with sigma of 0.02
 O2-O2_$1 \\sim O2A-O2A_$1
 with sigma of 0.02
3. Restrained planarity
 O2A, N3, O3, O2A_$1
 with sigma of 0.1
 O2, O2_$1, N3, O3
 with sigma of 0.1
4. Uiso/Uaniso restraints and constraints
O2A \\sim O2 \\sim N3 \\sim Cu1: within 2A with sigma of 0.01 and sigma for
terminal atoms of 0.02 within 2A
5. Rigid body (RIGU) restrains
 Cu1, O2A, O2, N3
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.02
6. Others
 Sof(O2A)=1-FVAR(1)
 Sof(O2)=FVAR(1)
7.a Ternary CH refined with riding coordinates:
 C7(H7)
7.b Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C9(H9A,H9B)
7.c Aromatic/amide H refined with riding coordinates:
 C1(H1), C3(H3), C4(H4), C5(H5)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_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
Cu1 Cu 0.250000 0.500000 0.31637(2) 0.03520(15) Uani 1 2 d DS T P . .
O1 O 0.59801(15) 0.4947(3) 0.43265(5) 0.0369(4) Uani 1 1 d . . . . .
O2 O 0.3005(10) 0.332(2) 0.24065(19) 0.0553(18) Uani 0.69(4) 1 d D U P A 1
O3 O 0.250000 0.500000 0.17592(9) 0.0726(10) Uani 1 2 d S T P A .
N1 N 0.37758(13) 0.6988(4) 0.32999(6) 0.0283(4) Uani 1 1 d . . . . .
N2 N 0.64096(14) 0.9260(3) 0.44002(6) 0.0243(4) Uani 1 1 d . . . . .
N3 N 0.250000 0.500000 0.21782(10) 0.0387(6) Uani 1 2 d DS TU P . .
C1 C 0.44154(16) 0.6484(4) 0.36592(7) 0.0260(4) Uani 1 1 d . . . . .
H1 H 0.424337 0.506580 0.384786 0.031 Uiso 1 1 calc R U . . .
C2 C 0.53159(15) 0.7951(4) 0.37653(6) 0.0228(4) Uani 1 1 d . . . . .
C3 C 0.55864(17) 1.0032(4) 0.34787(7) 0.0296(5) Uani 1 1 d . . . . .
H3 H 0.619271 1.104759 0.353648 0.036 Uiso 1 1 calc R U . . .
C4 C 0.4938(2) 1.0564(5) 0.31065(7) 0.0348(5) Uani 1 1 d . . . . .
H4 H 0.510117 1.195307 0.291011 0.042 Uiso 1 1 calc R U . . .
C5 C 0.40441(18) 0.9016(5) 0.30273(7) 0.0325(5) Uani 1 1 d . . . . .
H5 H 0.361207 0.939497 0.277541 0.039 Uiso 1 1 calc R U . . .
C6 C 0.59410(15) 0.7229(4) 0.41876(7) 0.0241(4) Uani 1 1 d . . . . .
C7 C 0.70569(15) 0.8957(4) 0.48141(6) 0.0217(4) Uani 1 1 d . . . . .
H7 H 0.739537 0.721370 0.480609 0.026 Uiso 1 1 calc R U . . .
C8 C 0.63775(17) 0.9140(5) 0.52485(7) 0.0298(5) Uani 1 1 d . . . . .
H8A H 0.599453 1.080442 0.525062 0.036 Uiso 1 1 calc R U . . .
H8B H 0.585123 0.773074 0.524880 0.036 Uiso 1 1 calc R U . . .
C9 C 0.70677(19) 0.8937(4) 0.56782(7) 0.0312(5) Uani 1 1 d . . . . .
H9A H 0.740226 0.721205 0.569055 0.037 Uiso 1 1 calc R U . . .
H9B H 0.661936 0.913407 0.594833 0.037 Uiso 1 1 calc R U . . .
H2 H 0.626(2) 1.086(5) 0.4325(7) 0.029(6) Uiso 1 1 d . . . . .
O2A O 0.3244(14) 0.398(6) 0.2396(4) 0.058(3) Uani 0.31(4) 1 d D U P A 2


_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
Cu1 O2 2.447(5) . ?
Cu1 O2 2.447(5) 2_565 ?
Cu1 N1 1.9241(17) 2_565 ?
Cu1 N1 1.9241(17) . ?
Cu1 O2A 2.474(12) . ?
Cu1 O2A 2.474(12) 2_565 ?
O1 C6 1.227(2) . ?
O2 N3 1.252(4) . ?
O3 N3 1.220(4) . ?
N1 C1 1.340(3) . ?
N1 C5 1.342(3) . ?
N2 C6 1.336(2) . ?
N2 C7 1.459(2) . ?
N2 H2 0.86(3) . ?
N3 O2A 1.237(9) 2_565 ?
N3 O2A 1.237(9) . ?
C1 H1 0.9300 . ?
C1 C2 1.382(3) . ?
C2 C3 1.387(3) . ?
C2 C6 1.501(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.378(3) . ?
C4 H4 0.9300 . ?
C4 C5 1.382(3) . ?
C5 H5 0.9300 . ?
C7 C7 1.529(4) 2_675 ?
C7 H7 0.9800 . ?
C7 C8 1.525(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C8 C9 1.522(3) . ?
C9 C9 1.524(4) 2_675 ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?

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
O2 Cu1 O2 51.39(19) . 2_565 ?
O2 Cu1 O2A 10.5(5) 2_565 2_565 ?
O2 Cu1 O2A 49.86(19) . 2_565 ?
N1 Cu1 O2 99.0(4) 2_565 2_565 ?
N1 Cu1 O2 102.4(4) . 2_565 ?
N1 Cu1 O2 102.4(4) 2_565 . ?
N1 Cu1 O2 99.0(4) . . ?
N1 Cu1 N1 156.21(10) 2_565 . ?
N1 Cu1 O2A 89.2(7) . . ?
N1 Cu1 O2A 112.7(7) . 2_565 ?
N1 Cu1 O2A 112.7(7) 2_565 . ?
N1 Cu1 O2A 89.2(7) 2_565 2_565 ?
O2A Cu1 O2A 50.8(4) 2_565 . ?
N3 O2 Cu1 96.4(3) . . ?
C1 N1 Cu1 123.53(14) . . ?
C1 N1 C5 117.40(18) . . ?
C5 N1 Cu1 119.07(14) . . ?
C6 N2 C7 122.90(17) . . ?
C6 N2 H2 121.1(16) . . ?
C7 N2 H2 115.3(15) . . ?
O2 N3 O2 115.8(5) 2_565 . ?
O3 N3 O2 122.1(3) . . ?
O3 N3 O2 122.1(3) . 2_565 ?
O3 N3 O2A 120.9(6) . . ?
O3 N3 O2A 120.9(6) . 2_565 ?
N1 C1 H1 118.1 . . ?
N1 C1 C2 123.70(18) . . ?
C2 C1 H1 118.1 . . ?
C1 C2 C3 118.21(18) . . ?
C1 C2 C6 118.25(17) . . ?
C3 C2 C6 123.53(17) . . ?
C2 C3 H3 120.7 . . ?
C4 C3 C2 118.66(19) . . ?
C4 C3 H3 120.7 . . ?
C3 C4 H4 120.3 . . ?
C3 C4 C5 119.5(2) . . ?
C5 C4 H4 120.3 . . ?
N1 C5 C4 122.5(2) . . ?
N1 C5 H5 118.7 . . ?
C4 C5 H5 118.7 . . ?
O1 C6 N2 123.87(19) . . ?
O1 C6 C2 121.37(18) . . ?
N2 C6 C2 114.73(17) . . ?
N2 C7 C7 109.04(13) . 2_675 ?
N2 C7 H7 108.3 . . ?
N2 C7 C8 111.83(17) . . ?
C7 C7 H7 108.3 2_675 . ?
C8 C7 C7 111.03(13) . 2_675 ?
C8 C7 H7 108.3 . . ?
C7 C8 H8A 109.4 . . ?
C7 C8 H8B 109.4 . . ?
H8A C8 H8B 108.0 . . ?
C9 C8 C7 111.35(17) . . ?
C9 C8 H8A 109.4 . . ?
C9 C8 H8B 109.4 . . ?
C8 C9 C9 110.59(15) . 2_675 ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9B 109.5 . . ?
C9 C9 H9A 109.5 2_675 . ?
C9 C9 H9B 109.5 2_675 . ?
H9A C9 H9B 108.1 . . ?
N3 O2A Cu1 95.5(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
Cu1 O2 N3 O2 0.000(3) . . . 2_565 ?
Cu1 O2 N3 O3 180.000(4) . . . . ?
Cu1 N1 C1 C2 -178.18(15) . . . . ?
Cu1 N1 C5 C4 178.96(18) . . . . ?
O3 N3 O2A Cu1 180.000(7) . . . . ?
N1 C1 C2 C3 -1.3(3) . . . . ?
N1 C1 C2 C6 177.89(18) . . . . ?
N2 C7 C8 C9 -177.59(16) . . . . ?
C1 N1 C5 C4 -0.2(3) . . . . ?
C1 C2 C3 C4 0.9(3) . . . . ?
C1 C2 C6 O1 30.4(3) . . . . ?
C1 C2 C6 N2 -147.64(19) . . . . ?
C2 C3 C4 C5 -0.3(3) . . . . ?
C3 C2 C6 O1 -150.4(2) . . . . ?
C3 C2 C6 N2 31.5(3) . . . . ?
C3 C4 C5 N1 -0.1(4) . . . . ?
C5 N1 C1 C2 1.0(3) . . . . ?
C6 N2 C7 C7 147.8(2) . . . 2_675 ?
C6 N2 C7 C8 -89.0(2) . . . . ?
C6 C2 C3 C4 -178.2(2) . . . . ?
C7 N2 C6 O1 2.4(3) . . . . ?
C7 N2 C6 C2 -179.58(17) . . . . ?
C7 C7 C8 C9 -55.5(3) 2_675 . . . ?
C7 C8 C9 C9 56.8(3) . . . 2_675 ?
O2A N3 O2A Cu1 0.000(4) 2_565 . . . ?

_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_luan
_audit_block_doi                 10.5517/ccdc.csd.cc2g7721
_database_code_depnum_ccdc_archive 'CCDC 2271062'
loop_
_audit_author_name
_audit_author_address
'Jian Luan'
;Northeastern University
China
;
_audit_update_record             
;
2023-06-20 deposited with the CCDC.	2023-07-27 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            'C18 H20 N4 O2'
_chemical_formula_weight         324.38

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           60
_space_group_name_H-M_alt        'P b c n'
_space_group_name_Hall           '-P 2n 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+1/2, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'-x-1/2, y-1/2, z'
'x, -y, z-1/2'

_cell_length_a                   18.636(3)
_cell_length_b                   9.2345(11)
_cell_length_c                   9.7862(13)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1684.2(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    27406
_cell_measurement_theta_min      2.186
_cell_measurement_theta_max      30.282

_exptl_crystal_description       BLOCK
_exptl_crystal_colour            COLOURLESS
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.279
_exptl_crystal_F_000             688
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.190
_exptl_absorpt_coefficient_mu    0.086
_shelx_estimated_absorpt_T_min   0.982
_shelx_estimated_absorpt_T_max   0.984
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.982
_exptl_absorpt_correction_T_max  0.984
_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 area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            25104
_diffrn_reflns_av_unetI/netI     0.0394
_diffrn_reflns_av_R_equivalents  0.0658
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.186
_diffrn_reflns_theta_max         30.282
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             2509
_reflns_number_gt                1441
_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       'Bruker Instrument Service vV6.2.9'
_computing_cell_refinement       'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS Inc., 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'DIAMOND, Vers. 3.2h (Brandenburg, 2012)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0569P)²+0.3148P] 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         2509
_refine_ls_number_parameters     109
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1085
_refine_ls_R_factor_gt           0.0524
_refine_ls_wR_factor_ref         0.1372
_refine_ls_wR_factor_gt          0.1147
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.021
_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 0.59381(7) 0.06784(12) 0.54465(10) 0.0618(4) Uani 1 1 d . . . . .
N1 N 0.72140(9) 0.40285(17) 0.68180(18) 0.0704(5) Uani 1 1 d . . . . .
C1 C 0.71992(10) 0.43347(19) 0.8140(2) 0.0611(5) Uani 1 1 d . . . . .
H1A H 0.746213 0.512851 0.844271 0.073 Uiso 1 1 calc R U . . .
N2 N 0.57733(6) -0.02179(12) 0.75597(11) 0.0392(3) Uani 1 1 d . . . . .
H2B H 0.585562 -0.009161 0.841618 0.047 Uiso 1 1 calc R U . . .
C2 C 0.68240(10) 0.35619(17) 0.90850(17) 0.0562(5) Uani 1 1 d . . . . .
H2A H 0.683195 0.382503 1.000221 0.067 Uiso 1 1 calc R U . . .
C3 C 0.68303(9) 0.28763(19) 0.64167(16) 0.0535(4) Uani 1 1 d . . . . .
H3A H 0.683432 0.263868 0.549321 0.064 Uiso 1 1 calc R U . . .
C4 C 0.64285(7) 0.20175(14) 0.72876(13) 0.0358(3) Uani 1 1 d . . . . .
C5 C 0.64324(9) 0.23831(17) 0.86549(15) 0.0502(4) Uani 1 1 d . . . . .
H5A H 0.617243 0.183686 0.928118 0.060 Uiso 1 1 calc R U . . .
C6 C 0.60235(8) 0.07642(14) 0.66921(13) 0.0370(3) Uani 1 1 d . . . . .
C7 C 0.53680(8) -0.14969(14) 0.71534(13) 0.0373(3) Uani 1 1 d . . . . .
H7A H 0.529542 -0.146200 0.616212 0.045 Uiso 1 1 calc R U . . .
C8 C 0.57840(9) -0.28697(16) 0.74951(18) 0.0517(4) Uani 1 1 d . . . . .
H8A H 0.623294 -0.287343 0.699350 0.062 Uiso 1 1 calc R U . . .
H8B H 0.589609 -0.287834 0.846303 0.062 Uiso 1 1 calc R U . . .
C9 C 0.53579(10) -0.42216(17) 0.7137(2) 0.0696(6) Uani 1 1 d . . . . .
H9A H 0.528096 -0.425870 0.615723 0.084 Uiso 1 1 calc R U . . .
H9B H 0.562851 -0.507460 0.739980 0.084 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 C6 1.2319(16) . ?
N1 C1 1.325(2) . ?
N1 C3 1.341(2) . ?
C1 C2 1.361(2) . ?
N2 C6 1.3269(17) . ?
N2 C7 1.4573(18) . ?
C2 C5 1.376(2) . ?
C3 C4 1.384(2) . ?
C4 C5 1.3800(19) . ?
C4 C6 1.500(2) . ?
C7 C8 1.523(2) . ?
C7 C7 1.530(3) 4_656 ?
C8 C9 1.521(2) . ?
C9 C9 1.512(4) 4_656 ?

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
C1 N1 C3 116.38(15) . . ?
N1 C1 C2 124.20(16) . . ?
C6 N2 C7 124.16(11) . . ?
C1 C2 C5 118.64(16) . . ?
N1 C3 C4 124.25(15) . . ?
C5 C4 C3 117.00(14) . . ?
C5 C4 C6 124.63(13) . . ?
C3 C4 C6 118.37(13) . . ?
C2 C5 C4 119.52(14) . . ?
O1 C6 N2 122.94(13) . . ?
O1 C6 C4 119.95(13) . . ?
N2 C6 C4 117.11(12) . . ?
N2 C7 C8 110.54(12) . . ?
N2 C7 C7 110.10(9) . 4_656 ?
C8 C7 C7 111.03(10) . 4_656 ?
C9 C8 C7 111.53(13) . . ?
C9 C9 C8 110.64(14) 4_656 . ?

_refine_diff_density_max         0.205
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.039



