# Supplementary Information (SI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2025

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

data_mo_pnwsci03b_0m
_database_code_depnum_ccdc_archive 'CCDC 2479263'
loop_
_audit_author_name
_audit_author_address
'Kraig Wheeler'
;Whitworth University
United States of America
;
_audit_update_record             
;
2025-08-08 deposited with the CCDC.	2025-10-31 downloaded from the CCDC.
;
_audit_creation_date             2025-07-24
_audit_creation_method           
;
Olex2 1.5
(compiled 2025.07.13 svn.rb7424aed for OlexSys, GUI svn.r7308)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C16 H16 N2 O2'
_chemical_formula_sum            'C16 H16 N2 O2'
_chemical_formula_weight         268.31
_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'
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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   9.6366(3)
_cell_length_b                   14.5962(5)
_cell_length_c                   9.6954(3)
_cell_angle_alpha                90
_cell_angle_beta                 98.9920(10)
_cell_angle_gamma                90
_cell_volume                     1346.97(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1150
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      25.68
_cell_measurement_theta_min      2.54
_shelx_estimated_absorpt_T_max   0.990
_shelx_estimated_absorpt_T_min   0.971
_exptl_absorpt_coefficient_mu    0.089
_exptl_absorpt_correction_T_max  0.7465
_exptl_absorpt_correction_T_min  0.7026
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker,2016/2) was used for absorption correction.
wR2(int) was 0.0763 before and 0.0447 after correction.
The Ratio of minimum to maximum transmission is 0.9412.
The λ/2 correction factor is Not present.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             568
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1.00 -1.00 1.00 0.1140
-1.00 1.00 -1.00 0.0280
1.00 -1.00 -1.00 0.0990
0.00 1.00 1.00 0.0620
0.00 -1.00 -1.00 0.0700
1.00 0.00 1.00 0.1040
0.00 1.00 0.00 0.0190
0.00 -1.00 0.00 0.0660
1.00 0.00 0.00 0.1330
-1.00 -1.00 0.00 0.0160

_exptl_crystal_size_max          0.33
_exptl_crystal_size_mid          0.226
_exptl_crystal_size_min          0.113
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0271
_diffrn_reflns_av_unetI/netI     0.0141
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            48893
_diffrn_reflns_point_group_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         33.141
_diffrn_reflns_theta_min         2.544
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 '100 \\times 140 mm^2^ CMOS sensor'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'Bruker PHOTON II'
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'κ-geometry four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_collimation    'focusing mirror'
_diffrn_radiation_detector       'Bruker PHOTON II'
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_type              'Incoatec I\mS 3.0'
_diffrn_standards_number         .
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4579
_reflns_number_total             5122
_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+ V8.40B (Bruker AXS Inc., 2020)'
_computing_data_collection       'APEX3 Ver.2019.11-0 (Bruker-AXS, 2019)'
_computing_data_reduction        'SAINT+ Ve8.40B (Bruker-AXS, 2020)'
_computing_molecular_graphics    'OLEX2 (Dolomanov et al., 2009)'
_computing_publication_material  'OLEX2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2019/1)'
_computing_structure_solution    'XT (Sheldrick, 2018/2)'
_refine_diff_density_max         0.460
_refine_diff_density_min         -0.272
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     189
_refine_ls_number_reflns         5122
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0428
_refine_ls_R_factor_gt           0.0386
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0666P)²+0.2983P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1139
_refine_ls_wR_factor_ref         0.1185
_refine_special_details          
;
All nonhydrogen atoms were located in a single difference Fourier 
electron density map and refined using anisotropic displacement 
parameters. All C-H hydrogen atoms were placed in calculated 
positions with Uiso = 1.2xUeqiv of the connected C atoms 
(1.5xUeqiv for methyl groups). Those H atoms attached to nitrogen 
and oxygen were located in Fourier diff mapsand assigned Uiso = 
1.2xUeqiv for NH groups (Uiso = 1.5xUeqiv for OH groups).
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Others
 Fixed Sof: H1(0.5) H2(0.5)
3.a Aromatic/amide H refined with riding coordinates:
 C1(H1A), C2(H2A), C3(H3), C4(H4), C7(H7), C10(H10), C11(H11), C13(H13),
 C14(H14)
3.b Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C16(H16A,H16B,H16C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_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
O1 O 0.60304(5) 0.61517(4) 0.57476(6) 0.01951(11) Uani 1 1 d . . . . .
H1 H 0.606(3) 0.5901(18) 0.487(3) 0.029 Uiso 0.5 1 d . U P A 1
O2 O 0.54371(5) 0.56440(4) 0.33026(5) 0.01838(11) Uani 1 1 d . . . . .
H2 H 0.584(3) 0.5748(18) 0.423(3) 0.028 Uiso 0.5 1 d . U P B 2
N1 N 0.30431(7) 0.71965(4) 0.68681(6) 0.02010(12) Uani 1 1 d . . . . .
N2 N 0.05642(7) 0.56480(5) -0.19251(6) 0.02161(13) Uani 1 1 d . . . . .
C1 C 0.26839(8) 0.75703(5) 0.80196(8) 0.02275(14) Uani 1 1 d . . . . .
H1A H 0.176096 0.781003 0.797038 0.027 Uiso 1 1 calc R U . . .
C2 C 0.35862(8) 0.76288(5) 0.92900(7) 0.02192(14) Uani 1 1 d . . . . .
H2A H 0.328381 0.790309 1.008063 0.026 Uiso 1 1 calc R U . . .
C3 C 0.49316(8) 0.72786(5) 0.93738(7) 0.02124(14) Uani 1 1 d . . . . .
H3 H 0.557426 0.731069 1.022177 0.025 Uiso 1 1 calc R U . . .
C4 C 0.53231(7) 0.68783(5) 0.81889(7) 0.01839(13) Uani 1 1 d . . . . .
H4 H 0.623666 0.662757 0.821548 0.022 Uiso 1 1 calc R U . . .
C5 C 0.43510(7) 0.68519(4) 0.69628(7) 0.01570(12) Uani 1 1 d . . . . .
C6 C 0.47372(7) 0.64351(4) 0.56739(7) 0.01577(12) Uani 1 1 d . . . . .
C7 C 0.37621(7) 0.63543(5) 0.44626(7) 0.01610(12) Uani 1 1 d . . . . .
H7 H 0.283029 0.657282 0.444053 0.019 Uiso 1 1 calc R U . . .
C8 C 0.41651(7) 0.59440(4) 0.32588(7) 0.01500(12) Uani 1 1 d . . . . .
C9 C 0.31989(7) 0.58501(4) 0.19479(7) 0.01472(12) Uani 1 1 d . . . . .
C10 C 0.18697(7) 0.62653(5) 0.17201(7) 0.01752(12) Uani 1 1 d . . . . .
H10 H 0.156480 0.660199 0.245603 0.021 Uiso 1 1 calc R U . . .
C11 C 0.09942(7) 0.61970(5) 0.04548(7) 0.01843(13) Uani 1 1 d . . . . .
H11 H 0.010362 0.649076 0.033181 0.022 Uiso 1 1 calc R U . . .
C12 C 0.14072(7) 0.56941(5) -0.06634(7) 0.01640(12) Uani 1 1 d . . . . .
C13 C 0.27301(7) 0.52481(5) -0.04200(7) 0.01706(12) Uani 1 1 d . . . . .
H13 H 0.302239 0.488468 -0.113506 0.020 Uiso 1 1 calc R U . . .
C14 C 0.35967(7) 0.53382(5) 0.08489(7) 0.01589(12) Uani 1 1 d . . . . .
H14 H 0.448789 0.504515 0.098135 0.019 Uiso 1 1 calc R U . . .
C15 C -0.08087(8) 0.60801(6) -0.21371(8) 0.02308(14) Uani 1 1 d . . . . .
H15A H -0.069622 0.674688 -0.207700 0.035 Uiso 1 1 calc R U . . .
H15B H -0.134408 0.587048 -0.141663 0.035 Uiso 1 1 calc R U . . .
H15C H -0.131295 0.591474 -0.306078 0.035 Uiso 1 1 calc R U . . .
C16 C 0.09887(10) 0.51382(8) -0.30691(9) 0.0348(2) Uani 1 1 d . . . . .
H16A H 0.028779 0.521956 -0.390819 0.052 Uiso 1 1 calc R U . . .
H16B H 0.106387 0.448656 -0.282517 0.052 Uiso 1 1 calc R U . . .
H16C H 0.190186 0.536302 -0.324877 0.052 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 H1 0.93(3) . ?
O1 C6 1.3043(8) . ?
O2 H2 0.93(3) . ?
O2 C8 1.2961(8) . ?
N1 C1 1.3359(9) . ?
N1 C5 1.3468(9) . ?
N2 C12 1.3602(9) . ?
N2 C15 1.4510(10) . ?
N2 C16 1.4467(10) . ?
C1 H1A 0.9500 . ?
C1 C2 1.3949(10) . ?
C2 H2A 0.9500 . ?
C2 C3 1.3842(11) . ?
C3 H3 0.9500 . ?
C3 C4 1.3925(10) . ?
C4 H4 0.9500 . ?
C4 C5 1.3943(9) . ?
C5 C6 1.4885(9) . ?
C6 C7 1.3897(9) . ?
C7 H7 0.9500 . ?
C7 C8 1.4189(9) . ?
C8 C9 1.4598(9) . ?
C9 C10 1.4030(9) . ?
C9 C14 1.4030(9) . ?
C10 H10 0.9500 . ?
C10 C11 1.3796(9) . ?
C11 H11 0.9500 . ?
C11 C12 1.4169(9) . ?
C12 C13 1.4180(9) . ?
C13 H13 0.9500 . ?
C13 C14 1.3809(9) . ?
C14 H14 0.9500 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 O1 H1 103.7(16) . . ?
C8 O2 H2 103.1(16) . . ?
C1 N1 C5 117.23(6) . . ?
C12 N2 C15 120.60(6) . . ?
C12 N2 C16 120.95(6) . . ?
C16 N2 C15 118.41(6) . . ?
N1 C1 H1A 118.1 . . ?
N1 C1 C2 123.77(7) . . ?
C2 C1 H1A 118.1 . . ?
C1 C2 H2A 120.7 . . ?
C3 C2 C1 118.56(7) . . ?
C3 C2 H2A 120.7 . . ?
C2 C3 H3 120.7 . . ?
C2 C3 C4 118.60(6) . . ?
C4 C3 H3 120.7 . . ?
C3 C4 H4 120.6 . . ?
C3 C4 C5 118.84(7) . . ?
C5 C4 H4 120.6 . . ?
N1 C5 C4 123.00(6) . . ?
N1 C5 C6 116.72(6) . . ?
C4 C5 C6 120.28(6) . . ?
O1 C6 C5 116.47(6) . . ?
O1 C6 C7 122.24(6) . . ?
C7 C6 C5 121.29(6) . . ?
C6 C7 H7 120.2 . . ?
C6 C7 C8 119.68(6) . . ?
C8 C7 H7 120.2 . . ?
O2 C8 C7 119.65(6) . . ?
O2 C8 C9 117.91(6) . . ?
C7 C8 C9 122.44(6) . . ?
C10 C9 C8 122.61(6) . . ?
C10 C9 C14 117.49(6) . . ?
C14 C9 C8 119.90(6) . . ?
C9 C10 H10 119.2 . . ?
C11 C10 C9 121.69(6) . . ?
C11 C10 H10 119.2 . . ?
C10 C11 H11 119.6 . . ?
C10 C11 C12 120.79(6) . . ?
C12 C11 H11 119.6 . . ?
N2 C12 C11 120.94(6) . . ?
N2 C12 C13 121.47(6) . . ?
C11 C12 C13 117.60(6) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 C12 120.49(6) . . ?
C14 C13 H13 119.8 . . ?
C9 C14 H14 119.1 . . ?
C13 C14 C9 121.89(6) . . ?
C13 C14 H14 119.1 . . ?
N2 C15 H15A 109.5 . . ?
N2 C15 H15B 109.5 . . ?
N2 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N2 C16 H16A 109.5 . . ?
N2 C16 H16B 109.5 . . ?
N2 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C6 C7 C8 0.58(10) . . . . ?
O2 C8 C9 C10 -170.60(6) . . . . ?
O2 C8 C9 C14 8.53(9) . . . . ?
N1 C1 C2 C3 -0.22(12) . . . . ?
N1 C5 C6 O1 176.05(6) . . . . ?
N1 C5 C6 C7 -4.05(9) . . . . ?
N2 C12 C13 C14 177.05(6) . . . . ?
C1 N1 C5 C4 -0.54(11) . . . . ?
C1 N1 C5 C6 179.84(6) . . . . ?
C1 C2 C3 C4 -0.38(11) . . . . ?
C2 C3 C4 C5 0.50(10) . . . . ?
C3 C4 C5 N1 -0.03(10) . . . . ?
C3 C4 C5 C6 179.57(6) . . . . ?
C4 C5 C6 O1 -3.58(9) . . . . ?
C4 C5 C6 C7 176.32(6) . . . . ?
C5 N1 C1 C2 0.67(12) . . . . ?
C5 C6 C7 C8 -179.31(6) . . . . ?
C6 C7 C8 O2 0.36(10) . . . . ?
C6 C7 C8 C9 -179.09(6) . . . . ?
C7 C8 C9 C10 8.87(10) . . . . ?
C7 C8 C9 C14 -172.01(6) . . . . ?
C8 C9 C10 C11 177.47(6) . . . . ?
C8 C9 C14 C13 -178.51(6) . . . . ?
C9 C10 C11 C12 0.55(11) . . . . ?
C10 C9 C14 C13 0.66(10) . . . . ?
C10 C11 C12 N2 -178.04(7) . . . . ?
C10 C11 C12 C13 1.57(10) . . . . ?
C11 C12 C13 C14 -2.56(10) . . . . ?
C12 C13 C14 C9 1.47(10) . . . . ?
C14 C9 C10 C11 -1.67(10) . . . . ?
C15 N2 C12 C11 -2.77(11) . . . . ?
C15 N2 C12 C13 177.64(7) . . . . ?
C16 N2 C12 C11 179.70(8) . . . . ?
C16 N2 C12 C13 0.11(12) . . . . ?

_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_25wdb01
_database_code_depnum_ccdc_archive 'CCDC 2479267'
loop_
_audit_author_name
_audit_author_address
'Kraig Wheeler'
;Whitworth University
United States of America
;
_audit_update_record             
;
2025-08-08 deposited with the CCDC.	2025-10-31 downloaded from the CCDC.
;
_audit_creation_date             2025-07-24
_audit_creation_method           
;
Olex2 1.5
(compiled 2025.07.13 svn.rb7424aed for OlexSys, GUI svn.r7308)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C27 H27 N7'
_chemical_formula_sum            'C27 H27 N7'
_chemical_formula_weight         449.55
_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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   9.8859(13)
_cell_length_b                   10.8489(14)
_cell_length_c                   20.943(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2246.2(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9767
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      72.35
_cell_measurement_theta_min      4.47
_shelx_estimated_absorpt_T_max   0.921
_shelx_estimated_absorpt_T_min   0.872
_exptl_absorpt_coefficient_mu    0.651
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_T_min  0.6878
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Krause et al., 2015) was used for absorption correction.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             952
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1.00 1.00 0.00 0.1350
-1.00 1.00 -1.00 0.1510
-1.00 -1.00 -1.00 0.1440
-1.00 -1.00 0.00 0.1430
-1.00 -1.00 1.00 0.1290
-1.00 0.00 0.00 0.1340
-1.00 0.00 1.00 0.1090
0.00 1.00 1.00 0.1070
0.00 -1.00 -1.00 0.1240
0.00 1.00 0.00 0.1200
0.00 -1.00 0.00 0.0940
0.00 1.00 -1.00 0.1250
0.00 0.00 1.00 0.0610
0.00 0.00 -1.00 0.1290
1.00 -1.00 0.00 0.0570
1.00 -1.00 1.00 0.0610
1.00 1.00 1.00 0.0530
1.00 1.00 0.00 0.0700
1.00 1.00 -1.00 0.0800
1.00 0.00 0.00 0.0430
1.00 0.00 -1.00 0.0740

_exptl_crystal_size_max          0.217
_exptl_crystal_size_mid          0.163
_exptl_crystal_size_min          0.128
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0355
_diffrn_reflns_av_unetI/netI     0.0204
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            31898
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.344
_diffrn_reflns_theta_min         4.590
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 '100 \\times 140 mm^2^ CMOS sensor'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'Bruker PHOTON II'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measurement_device       'κ-geometry four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_collimation    'focusing mirror'
_diffrn_radiation_detector       'Bruker PHOTON II'
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.1
_diffrn_source_power             0.05500000000000001
_diffrn_source_type              'Incoatec I\mS 3.0'
_diffrn_source_voltage           50.0
_diffrn_standards_number         .
_reflns_Friedel_coverage         0.752
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.992
_reflns_number_gt                4322
_reflns_number_total             4421
_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+ V8.40B (Bruker AXS Inc., 2020)'
_computing_data_collection       'APEX5 Ver.2022.08-RC130 (Bruker-AXS, 2023)'
_computing_data_reduction        'SAINT+ Ve8.40B (Bruker-AXS, 2020)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL  (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.147
_refine_diff_density_min         -0.141
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details 
;
 Flack x determined using 1832 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.12(8)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     317
_refine_ls_number_reflns         4421
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0270
_refine_ls_R_factor_gt           0.0262
_refine_ls_restrained_S_all      1.044
_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)+(0.0342P)²+0.4657P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0663
_refine_ls_wR_factor_ref         0.0670
_refine_special_details          
;
All nonhydrogen atoms were located in a single difference Fourier 
electron density map and refined using anisotropic displacement 
parameters. All C-H hydrogen atoms were placed in calculated 
positions with Uiso = 1.2xUeqiv of the connected C atoms 
(1.5xUeqiv for methyl groups). Those H atoms attached to nitrogen 
were located in Fourier diff mapsand assigned Uiso = 
1.2xUeqiv for NH groups.
;
_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.a Aromatic/amide H refined with riding coordinates:
 C2(H2A), C3(H3), C4(H4), C7(H7), C10(H10), C11(H11), C13(H13), C14(H14),
 C18(H18), C21(H21), C22(H22), C24(H24), C25(H25)
2.b Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C26(H26A,H26B,H26C), C27(H27A,H27B,
 H27C)
;
_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
N1 N 0.38098(14) 0.45876(12) 0.66875(6) 0.0194(3) Uani 1 1 d . . . . .
N2 N 0.45404(14) 0.28498(12) 0.58241(7) 0.0194(3) Uani 1 1 d . . . . .
H2 H 0.480(2) 0.2697(19) 0.6223(10) 0.023 Uiso 1 1 d . U . . .
N3 N 0.47293(14) 0.20042(13) 0.53569(6) 0.0195(3) Uani 1 1 d . . . . .
N4 N 0.36003(15) -0.06050(14) 0.26576(7) 0.0261(3) Uani 1 1 d . . . . .
N5 N 0.41896(14) 0.59306(12) 0.82443(6) 0.0204(3) Uani 1 1 d . . . . .
N6 N 0.42489(14) 0.52445(13) 0.87876(7) 0.0201(3) Uani 1 1 d . . . . .
H6 H 0.450(2) 0.5622(19) 0.9147(10) 0.024 Uiso 1 1 d . U . . .
N7 N 0.40929(16) 0.04357(13) 1.06557(7) 0.0253(3) Uani 1 1 d . . . . .
C1 C 0.36601(16) 0.54902(15) 0.71197(8) 0.0195(3) Uani 1 1 d . . . . .
C2 C 0.33180(16) 0.66951(15) 0.69507(8) 0.0218(3) Uani 1 1 d . . . . .
H2A H 0.324564 0.732067 0.726626 0.026 Uiso 1 1 calc R U . . .
C3 C 0.30853(17) 0.69600(15) 0.63104(8) 0.0221(3) Uani 1 1 d . . . . .
H3 H 0.283942 0.777029 0.618352 0.027 Uiso 1 1 calc R U . . .
C4 C 0.32145(16) 0.60345(15) 0.58587(8) 0.0205(3) Uani 1 1 d . . . . .
H4 H 0.304496 0.619059 0.541962 0.025 Uiso 1 1 calc R U . . .
C5 C 0.35998(15) 0.48701(15) 0.60681(8) 0.0186(3) Uani 1 1 d . . . . .
C6 C 0.38471(16) 0.38442(14) 0.56230(8) 0.0187(3) Uani 1 1 d . . . . .
C7 C 0.35467(16) 0.36395(14) 0.49870(8) 0.0189(3) Uani 1 1 d . . . . .
H7 H 0.306004 0.416690 0.470710 0.023 Uiso 1 1 calc R U . . .
C8 C 0.41171(15) 0.24802(15) 0.48422(7) 0.0180(3) Uani 1 1 d . . . . .
C9 C 0.40617(16) 0.17624(14) 0.42447(7) 0.0181(3) Uani 1 1 d . . . . .
C10 C 0.29543(17) 0.18661(15) 0.38352(8) 0.0208(3) Uani 1 1 d . . . . .
H10 H 0.229002 0.247902 0.391669 0.025 Uiso 1 1 calc R U . . .
C11 C 0.28009(17) 0.10943(15) 0.33116(8) 0.0212(3) Uani 1 1 d . . . . .
H11 H 0.202499 0.117646 0.304739 0.025 Uiso 1 1 calc R U . . .
C12 C 0.37754(17) 0.01926(15) 0.31656(7) 0.0202(3) Uani 1 1 d . . . . .
C13 C 0.49270(17) 0.01379(15) 0.35608(8) 0.0215(3) Uani 1 1 d . . . . .
H13 H 0.562818 -0.043113 0.346428 0.026 Uiso 1 1 calc R U . . .
C14 C 0.50534(16) 0.09020(16) 0.40890(8) 0.0203(3) Uani 1 1 d . . . . .
H14 H 0.583519 0.083632 0.435056 0.024 Uiso 1 1 calc R U . . .
C15 C 0.23048(19) -0.06532(17) 0.23385(8) 0.0280(4) Uani 1 1 d . . . . .
H15A H 0.158724 -0.077447 0.265524 0.042 Uiso 1 1 calc R U . . .
H15B H 0.229867 -0.133977 0.203446 0.042 Uiso 1 1 calc R U . . .
H15C H 0.215010 0.012193 0.210964 0.042 Uiso 1 1 calc R U . . .
C16 C 0.4553(2) -0.15995(18) 0.25575(9) 0.0321(4) Uani 1 1 d . . . . .
H16A H 0.545647 -0.125679 0.248269 0.048 Uiso 1 1 calc R U . . .
H16B H 0.427446 -0.208574 0.218570 0.048 Uiso 1 1 calc R U . . .
H16C H 0.457341 -0.212942 0.293635 0.048 Uiso 1 1 calc R U . . .
C17 C 0.38494(15) 0.51176(14) 0.77919(8) 0.0188(3) Uani 1 1 d . . . . .
C18 C 0.37026(17) 0.39233(15) 0.80436(8) 0.0212(3) Uani 1 1 d . . . . .
H18 H 0.347192 0.319372 0.781760 0.025 Uiso 1 1 calc R U . . .
C19 C 0.39648(16) 0.40354(14) 0.86892(8) 0.0198(3) Uani 1 1 d . . . . .
C20 C 0.39670(16) 0.31362(14) 0.92095(8) 0.0195(3) Uani 1 1 d . . . . .
C21 C 0.46790(17) 0.33336(15) 0.97778(8) 0.0214(3) Uani 1 1 d . . . . .
H21 H 0.515404 0.408676 0.983496 0.026 Uiso 1 1 calc R U . . .
C22 C 0.47086(17) 0.24605(16) 1.02580(8) 0.0215(3) Uani 1 1 d . . . . .
H22 H 0.519449 0.262758 1.063964 0.026 Uiso 1 1 calc R U . . .
C23 C 0.40301(17) 0.13277(15) 1.01904(8) 0.0204(3) Uani 1 1 d . . . . .
C24 C 0.32829(17) 0.11410(16) 0.96228(8) 0.0220(3) Uani 1 1 d . . . . .
H24 H 0.278563 0.039924 0.956790 0.026 Uiso 1 1 calc R U . . .
C25 C 0.32666(17) 0.20225(15) 0.91472(8) 0.0219(3) Uani 1 1 d . . . . .
H25 H 0.276684 0.186860 0.876808 0.026 Uiso 1 1 calc R U . . .
C26 C 0.4979(2) 0.05689(18) 1.11991(9) 0.0314(4) Uani 1 1 d . . . . .
H26A H 0.584457 0.091753 1.105951 0.047 Uiso 1 1 calc R U . . .
H26B H 0.513426 -0.024030 1.139380 0.047 Uiso 1 1 calc R U . . .
H26C H 0.456055 0.111977 1.151290 0.047 Uiso 1 1 calc R U . . .
C27 C 0.32796(18) -0.06685(16) 1.05999(9) 0.0263(4) Uani 1 1 d . . . . .
H27A H 0.231895 -0.044841 1.061865 0.039 Uiso 1 1 calc R U . . .
H27B H 0.349611 -0.123103 1.095148 0.039 Uiso 1 1 calc R U . . .
H27C H 0.347300 -0.107376 1.019179 0.039 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
N1 C1 1.342(2) . ?
N1 C5 1.349(2) . ?
N2 H2 0.89(2) . ?
N2 N3 1.3542(19) . ?
N2 C6 1.346(2) . ?
N3 C8 1.340(2) . ?
N4 C12 1.382(2) . ?
N4 C15 1.445(2) . ?
N4 C16 1.448(2) . ?
N5 N6 1.3610(19) . ?
N5 C17 1.337(2) . ?
N6 H6 0.89(2) . ?
N6 C19 1.357(2) . ?
N7 C23 1.375(2) . ?
N7 C26 1.443(2) . ?
N7 C27 1.448(2) . ?
C1 C2 1.396(2) . ?
C1 C17 1.477(2) . ?
C2 H2A 0.9500 . ?
C2 C3 1.391(2) . ?
C3 H3 0.9500 . ?
C3 C4 1.385(2) . ?
C4 H4 0.9500 . ?
C4 C5 1.390(2) . ?
C5 C6 1.472(2) . ?
C6 C7 1.383(2) . ?
C7 H7 0.9500 . ?
C7 C8 1.411(2) . ?
C8 C9 1.475(2) . ?
C9 C10 1.395(2) . ?
C9 C14 1.392(2) . ?
C10 H10 0.9500 . ?
C10 C11 1.388(2) . ?
C11 H11 0.9500 . ?
C11 C12 1.407(2) . ?
C12 C13 1.409(2) . ?
C13 H13 0.9500 . ?
C13 C14 1.388(2) . ?
C14 H14 0.9500 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 C18 1.406(2) . ?
C18 H18 0.9500 . ?
C18 C19 1.382(2) . ?
C19 C20 1.463(2) . ?
C20 C21 1.399(2) . ?
C20 C25 1.399(2) . ?
C21 H21 0.9500 . ?
C21 C22 1.382(2) . ?
C22 H22 0.9500 . ?
C22 C23 1.407(2) . ?
C23 C24 1.414(2) . ?
C24 H24 0.9500 . ?
C24 C25 1.381(2) . ?
C25 H25 0.9500 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C5 117.77(14) . . ?
N3 N2 H2 121.0(13) . . ?
C6 N2 H2 126.0(13) . . ?
C6 N2 N3 112.78(13) . . ?
C8 N3 N2 104.96(13) . . ?
C12 N4 C15 119.30(14) . . ?
C12 N4 C16 119.77(14) . . ?
C15 N4 C16 118.86(15) . . ?
C17 N5 N6 104.03(13) . . ?
N5 N6 H6 117.8(13) . . ?
C19 N6 N5 113.11(14) . . ?
C19 N6 H6 129.0(13) . . ?
C23 N7 C26 121.05(14) . . ?
C23 N7 C27 120.02(14) . . ?
C26 N7 C27 118.93(14) . . ?
N1 C1 C2 122.63(15) . . ?
N1 C1 C17 115.43(14) . . ?
C2 C1 C17 121.93(14) . . ?
C1 C2 H2A 120.7 . . ?
C3 C2 C1 118.56(15) . . ?
C3 C2 H2A 120.7 . . ?
C2 C3 H3 120.2 . . ?
C4 C3 C2 119.57(15) . . ?
C4 C3 H3 120.2 . . ?
C3 C4 H4 121.0 . . ?
C3 C4 C5 117.93(15) . . ?
C5 C4 H4 121.0 . . ?
N1 C5 C4 123.49(15) . . ?
N1 C5 C6 114.30(14) . . ?
C4 C5 C6 122.20(15) . . ?
N2 C6 C5 119.51(14) . . ?
N2 C6 C7 106.39(14) . . ?
C7 C6 C5 134.08(15) . . ?
C6 C7 H7 127.3 . . ?
C6 C7 C8 105.33(14) . . ?
C8 C7 H7 127.3 . . ?
N3 C8 C7 110.55(14) . . ?
N3 C8 C9 119.73(14) . . ?
C7 C8 C9 129.65(14) . . ?
C10 C9 C8 120.53(15) . . ?
C14 C9 C8 121.77(14) . . ?
C14 C9 C10 117.55(15) . . ?
C9 C10 H10 119.2 . . ?
C11 C10 C9 121.51(15) . . ?
C11 C10 H10 119.2 . . ?
C10 C11 H11 119.5 . . ?
C10 C11 C12 121.09(15) . . ?
C12 C11 H11 119.5 . . ?
N4 C12 C11 121.12(15) . . ?
N4 C12 C13 121.81(15) . . ?
C11 C12 C13 117.07(15) . . ?
C12 C13 H13 119.5 . . ?
C14 C13 C12 121.05(15) . . ?
C14 C13 H13 119.5 . . ?
C9 C14 H14 119.2 . . ?
C13 C14 C9 121.58(15) . . ?
C13 C14 H14 119.2 . . ?
N4 C15 H15A 109.5 . . ?
N4 C15 H15B 109.5 . . ?
N4 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N4 C16 H16A 109.5 . . ?
N4 C16 H16B 109.5 . . ?
N4 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N5 C17 C1 121.78(14) . . ?
N5 C17 C18 111.60(14) . . ?
C18 C17 C1 126.62(14) . . ?
C17 C18 H18 127.3 . . ?
C19 C18 C17 105.44(14) . . ?
C19 C18 H18 127.3 . . ?
N6 C19 C18 105.81(15) . . ?
N6 C19 C20 122.08(15) . . ?
C18 C19 C20 132.10(15) . . ?
C21 C20 C19 122.17(14) . . ?
C25 C20 C19 120.40(14) . . ?
C25 C20 C21 117.42(15) . . ?
C20 C21 H21 119.2 . . ?
C22 C21 C20 121.65(15) . . ?
C22 C21 H21 119.2 . . ?
C21 C22 H22 119.5 . . ?
C21 C22 C23 121.03(15) . . ?
C23 C22 H22 119.5 . . ?
N7 C23 C22 121.46(15) . . ?
N7 C23 C24 121.24(14) . . ?
C22 C23 C24 117.29(15) . . ?
C23 C24 H24 119.6 . . ?
C25 C24 C23 120.88(15) . . ?
C25 C24 H24 119.6 . . ?
C20 C25 H25 119.2 . . ?
C24 C25 C20 121.68(15) . . ?
C24 C25 H25 119.2 . . ?
N7 C26 H26A 109.5 . . ?
N7 C26 H26B 109.5 . . ?
N7 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
N7 C27 H27A 109.5 . . ?
N7 C27 H27B 109.5 . . ?
N7 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N2 H2 N5 0.89(2) 2.43(2) 3.1175(19) 134.0(17) 3_646 yes
N6 H6 N2 0.89(2) 2.60(2) 3.1753(19) 123.3(16) 3_656 yes
N6 H6 N3 0.89(2) 1.98(2) 2.806(2) 154.1(18) 3_656 yes

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 1.9(2) . . . . ?
N1 C1 C17 N5 156.74(15) . . . . ?
N1 C1 C17 C18 -23.6(2) . . . . ?
N1 C5 C6 N2 -15.6(2) . . . . ?
N1 C5 C6 C7 166.53(17) . . . . ?
N2 N3 C8 C7 0.40(18) . . . . ?
N2 N3 C8 C9 -176.79(13) . . . . ?
N2 C6 C7 C8 -0.36(17) . . . . ?
N3 N2 C6 C5 -177.78(13) . . . . ?
N3 N2 C6 C7 0.64(18) . . . . ?
N3 C8 C9 C10 147.12(16) . . . . ?
N3 C8 C9 C14 -28.4(2) . . . . ?
N4 C12 C13 C14 -176.55(15) . . . . ?
N5 N6 C19 C18 -0.07(18) . . . . ?
N5 N6 C19 C20 -179.78(14) . . . . ?
N5 C17 C18 C19 0.39(19) . . . . ?
N6 N5 C17 C1 179.31(14) . . . . ?
N6 N5 C17 C18 -0.42(18) . . . . ?
N6 C19 C20 C21 -22.2(2) . . . . ?
N6 C19 C20 C25 159.10(15) . . . . ?
N7 C23 C24 C25 -177.53(15) . . . . ?
C1 N1 C5 C4 -1.2(2) . . . . ?
C1 N1 C5 C6 177.26(13) . . . . ?
C1 C2 C3 C4 -0.8(2) . . . . ?
C1 C17 C18 C19 -179.32(15) . . . . ?
C2 C1 C17 N5 -24.7(2) . . . . ?
C2 C1 C17 C18 155.01(16) . . . . ?
C2 C3 C4 C5 -1.1(2) . . . . ?
C3 C4 C5 N1 2.3(2) . . . . ?
C3 C4 C5 C6 -176.15(14) . . . . ?
C4 C5 C6 N2 162.96(15) . . . . ?
C4 C5 C6 C7 -14.9(3) . . . . ?
C5 N1 C1 C2 -0.9(2) . . . . ?
C5 N1 C1 C17 177.68(14) . . . . ?
C5 C6 C7 C8 177.74(16) . . . . ?
C6 N2 N3 C8 -0.65(17) . . . . ?
C6 C7 C8 N3 -0.03(18) . . . . ?
C6 C7 C8 C9 176.80(15) . . . . ?
C7 C8 C9 C10 -29.5(2) . . . . ?
C7 C8 C9 C14 154.97(16) . . . . ?
C8 C9 C10 C11 -172.09(15) . . . . ?
C8 C9 C14 C13 173.19(15) . . . . ?
C9 C10 C11 C12 -1.4(2) . . . . ?
C10 C9 C14 C13 -2.5(2) . . . . ?
C10 C11 C12 N4 177.69(15) . . . . ?
C10 C11 C12 C13 -2.0(2) . . . . ?
C11 C12 C13 C14 3.2(2) . . . . ?
C12 C13 C14 C9 -0.9(3) . . . . ?
C14 C9 C10 C11 3.7(2) . . . . ?
C15 N4 C12 C11 -10.4(2) . . . . ?
C15 N4 C12 C13 169.25(16) . . . . ?
C16 N4 C12 C11 -173.92(16) . . . . ?
C16 N4 C12 C13 5.8(2) . . . . ?
C17 N5 N6 C19 0.30(17) . . . . ?
C17 C1 C2 C3 -176.57(15) . . . . ?
C17 C18 C19 N6 -0.18(18) . . . . ?
C17 C18 C19 C20 179.49(16) . . . . ?
C18 C19 C20 C21 158.17(18) . . . . ?
C18 C19 C20 C25 -20.5(3) . . . . ?
C19 C20 C21 C22 -177.92(15) . . . . ?
C19 C20 C25 C24 178.09(15) . . . . ?
C20 C21 C22 C23 0.6(2) . . . . ?
C21 C20 C25 C24 -0.7(2) . . . . ?
C21 C22 C23 N7 177.66(15) . . . . ?
C21 C22 C23 C24 -2.1(2) . . . . ?
C22 C23 C24 C25 2.3(2) . . . . ?
C23 C24 C25 C20 -0.9(2) . . . . ?
C25 C20 C21 C22 0.8(2) . . . . ?
C26 N7 C23 C22 -7.1(2) . . . . ?
C26 N7 C23 C24 172.73(17) . . . . ?
C27 N7 C23 C22 174.02(15) . . . . ?
C27 N7 C23 C24 -6.2(2) . . . . ?

_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_cu_sci22_13_0m
_database_code_depnum_ccdc_archive 'CCDC 2479265'
loop_
_audit_author_name
_audit_author_address
'Kraig Wheeler'
;Whitworth University
United States of America
;
_audit_update_record             
;
2025-08-08 deposited with the CCDC.	2025-10-31 downloaded from the CCDC.
;
_audit_creation_date             2025-07-24
_audit_creation_method           
;
Olex2 1.5
(compiled 2025.07.13 svn.rb7424aed for OlexSys, GUI svn.r7308)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C27 H27 N3 O4'
_chemical_formula_sum            'C27 H27 N3 O4'
_chemical_formula_weight         457.51
_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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   6.098(3)
_cell_length_b                   14.862(10)
_cell_length_c                   24.487(15)
_cell_angle_alpha                90
_cell_angle_beta                 92.87(3)
_cell_angle_gamma                90
_cell_volume                     2217(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    7510
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      76.12
_cell_measurement_theta_min      4.45
_shelx_estimated_absorpt_T_max   0.925
_shelx_estimated_absorpt_T_min   0.863
_exptl_absorpt_coefficient_mu    0.754
_exptl_absorpt_correction_T_max  0.7533
_exptl_absorpt_correction_T_min  0.6376
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Krause et al., 2015) was used for absorption correction.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear orange'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    orange
_exptl_crystal_density_diffrn    1.371
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             968
_exptl_crystal_size_max          0.201
_exptl_crystal_size_mid          0.178
_exptl_crystal_size_min          0.105
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0928
_diffrn_reflns_av_unetI/netI     0.0467
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            24670
_diffrn_reflns_point_group_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.404
_diffrn_reflns_theta_min         3.480
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 '100 \\times 140 mm^2^ CMOS sensor'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'Bruker PHOTON II'
_diffrn_measured_fraction_theta_full 0.989
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_device       'κ-geometry four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_collimation    'focusing mirror'
_diffrn_radiation_detector       'Bruker PHOTON II'
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.1
_diffrn_source_power             0.05500000000000001
_diffrn_source_type              'Incoatec I\mS 3.0'
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3066
_reflns_number_total             4179
_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+ V8.40B (Bruker AXS Inc., 2020)'
_computing_data_collection       'APEX5 Ver.2022.08-RC130 (Bruker-AXS, 2023)'
_computing_data_reduction        'SAINT+ Ve8.40B (Bruker-AXS, 2020)'
_computing_molecular_graphics    'OLEX2 (Dolomanov et al., 2009)'
_computing_publication_material  'OLEX2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2019/1)'
_computing_structure_solution    'XT (Sheldrick, 2018/2)'
_refine_diff_density_max         0.283
_refine_diff_density_min         -0.344
_refine_diff_density_rms         0.073
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     317
_refine_ls_number_reflns         4179
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0923
_refine_ls_R_factor_gt           0.0555
_refine_ls_restrained_S_all      1.086
_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)+(0.0630P)²+1.8301P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1322
_refine_ls_wR_factor_ref         0.1601
_refine_special_details          
;
All nonhydrogen atoms were located in a single difference Fourier 
electron density map and refined using anisotropic displacement 
parameters. All C-H hydrogen atoms were placed in calculated 
positions with Uiso = 1.2xUeqiv of the connected C atoms 
(1.5xUeqiv for methyl groups). Those H atoms attached to nitrogen 
and oxygen were located in Fourier diff mapsand assigned Uiso = 
1.2xUeqiv for NH groups (Uiso = 1.5xUeqiv for OH groups).
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 O1-H1 = O3-H3
 0.85 with sigma of 0.01
3.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3A), C4(H4), C7(H7), C10(H10), C11(H11), C13(H13), C14(H14),
 C18(H18), C21(H21), C22(H22), C24(H24), C25(H25)
3.b Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C26(H26A,H26B,H26C), C27(H27A,H27B,
 H27C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_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
O1 O -0.3765(3) 0.49556(13) 0.59398(7) 0.0315(4) Uani 1 1 d D . . . .
O2 O -0.3290(3) 0.52723(13) 0.69285(7) 0.0327(4) Uani 1 1 d . . . . .
H1 H -0.396(6) 0.510(2) 0.6274(6) 0.049 Uiso 1 1 d D U . . .
O3 O 0.4268(3) 0.22814(12) 0.47653(7) 0.0300(4) Uani 1 1 d D . . . .
H3 H 0.542(3) 0.203(2) 0.4915(13) 0.045 Uiso 1 1 d D U . A 1
O4 O 0.7384(3) 0.17609(12) 0.54128(7) 0.0286(4) Uani 1 1 d . . . . .
N1 N 0.0717(3) 0.36362(13) 0.55269(8) 0.0219(4) Uani 1 1 d . . . . .
N2 N 0.3009(4) 0.45826(15) 0.90300(9) 0.0301(5) Uani 1 1 d . . . . .
N3 N 1.0794(3) 0.22236(13) 0.79065(8) 0.0251(5) Uani 1 1 d . . . . .
C1 C 0.1490(4) 0.32452(15) 0.50858(9) 0.0223(5) Uani 1 1 d . . . . .
C2 C 0.0480(4) 0.33445(16) 0.45663(10) 0.0260(5) Uani 1 1 d . . . . .
H2 H 0.109259 0.307760 0.425600 0.031 Uiso 1 1 calc R U . . .
C3 C -0.1437(4) 0.38414(17) 0.45136(10) 0.0284(5) Uani 1 1 d . . . . .
H3A H -0.217535 0.391415 0.416553 0.034 Uiso 1 1 calc R U . . .
C4 C -0.2267(4) 0.42306(16) 0.49719(10) 0.0262(5) Uani 1 1 d . . . . .
H4 H -0.359358 0.456642 0.494518 0.031 Uiso 1 1 calc R U . . .
C5 C -0.1129(4) 0.41218(15) 0.54708(9) 0.0223(5) Uani 1 1 d . . . . .
C6 C -0.1888(4) 0.45404(15) 0.59790(10) 0.0239(5) Uani 1 1 d . . . . .
C7 C -0.0635(4) 0.44833(16) 0.64668(9) 0.0239(5) Uani 1 1 d . . . . .
H7 H 0.075021 0.418990 0.647589 0.029 Uiso 1 1 calc R U . . .
C8 C -0.1409(4) 0.48572(15) 0.69458(10) 0.0242(5) Uani 1 1 d . . . . .
C9 C -0.0206(4) 0.48008(15) 0.74759(10) 0.0230(5) Uani 1 1 d . . . . .
C10 C 0.1854(4) 0.43865(16) 0.75468(10) 0.0252(5) Uani 1 1 d . . . . .
H10 H 0.251599 0.413715 0.723800 0.030 Uiso 1 1 calc R U . . .
C11 C 0.2938(4) 0.43316(16) 0.80486(10) 0.0258(5) Uani 1 1 d . . . . .
H11 H 0.434375 0.405533 0.808029 0.031 Uiso 1 1 calc R U . . .
C12 C 0.1999(4) 0.46795(15) 0.85203(10) 0.0236(5) Uani 1 1 d . . . . .
C13 C -0.0035(4) 0.51240(15) 0.84483(10) 0.0245(5) Uani 1 1 d . . . . .
H13 H -0.068030 0.539137 0.875403 0.029 Uiso 1 1 calc R U . . .
C14 C -0.1097(4) 0.51753(15) 0.79408(10) 0.0248(5) Uani 1 1 d . . . . .
H14 H -0.247509 0.547326 0.790423 0.030 Uiso 1 1 calc R U . . .
C15 C 0.4979(5) 0.4053(2) 0.91099(12) 0.0373(6) Uani 1 1 d . . . . .
H15A H 0.622001 0.438053 0.896577 0.056 Uiso 1 1 calc R U . . .
H15B H 0.479061 0.347845 0.891713 0.056 Uiso 1 1 calc R U . . .
H15C H 0.526727 0.394066 0.950133 0.056 Uiso 1 1 calc R U . . .
C16 C 0.1977(5) 0.49381(18) 0.95025(10) 0.0321(6) Uani 1 1 d . . . . .
H16A H 0.186933 0.559423 0.947208 0.048 Uiso 1 1 calc R U . . .
H16B H 0.285901 0.478013 0.983425 0.048 Uiso 1 1 calc R U . . .
H16C H 0.050323 0.468101 0.952172 0.048 Uiso 1 1 calc R U . . .
C17 C 0.3522(4) 0.27067(15) 0.51832(10) 0.0235(5) Uani 1 1 d . . . . .
C18 C 0.4530(4) 0.26706(15) 0.57002(10) 0.0231(5) Uani 1 1 d . . . . .
H18 H 0.387483 0.297024 0.599353 0.028 Uiso 1 1 calc R U . . .
C19 C 0.6521(4) 0.21953(15) 0.58015(10) 0.0231(5) Uani 1 1 d . . . . .
C20 C 0.7622(4) 0.21998(15) 0.63450(9) 0.0210(5) Uani 1 1 d . . . . .
C21 C 0.6656(4) 0.25897(16) 0.67970(10) 0.0231(5) Uani 1 1 d . . . . .
H21 H 0.524520 0.285750 0.674771 0.028 Uiso 1 1 calc R U . . .
C22 C 0.7685(4) 0.25951(16) 0.73049(10) 0.0241(5) Uani 1 1 d . . . . .
H22 H 0.698090 0.286797 0.760019 0.029 Uiso 1 1 calc R U . . .
C23 C 0.9783(4) 0.22008(14) 0.73993(9) 0.0212(5) Uani 1 1 d . . . . .
C24 C 1.0754(4) 0.18072(15) 0.69439(9) 0.0224(5) Uani 1 1 d . . . . .
H24 H 1.216373 0.153748 0.699005 0.027 Uiso 1 1 calc R U . . .
C25 C 0.9691(4) 0.18092(15) 0.64366(10) 0.0226(5) Uani 1 1 d . . . . .
H25 H 1.038179 0.153702 0.613909 0.027 Uiso 1 1 calc R U . . .
C26 C 0.9583(4) 0.25036(18) 0.83738(10) 0.0295(6) Uani 1 1 d . . . . .
H26A H 0.907098 0.312369 0.831952 0.044 Uiso 1 1 calc R U . . .
H26B H 1.054337 0.247017 0.870622 0.044 Uiso 1 1 calc R U . . .
H26C H 0.831759 0.210554 0.841076 0.044 Uiso 1 1 calc R U . . .
C27 C 1.2818(4) 0.17305(19) 0.80248(10) 0.0308(6) Uani 1 1 d . . . . .
H27A H 1.248015 0.109373 0.808172 0.046 Uiso 1 1 calc R U . . .
H27B H 1.356545 0.197535 0.835587 0.046 Uiso 1 1 calc R U . . .
H27C H 1.377321 0.178976 0.771677 0.046 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 H1 0.862(10) . ?
O1 C6 1.299(3) . ?
O2 C8 1.301(3) . ?
O3 H3 0.860(10) . ?
O3 C17 1.304(3) . ?
O4 C19 1.284(3) . ?
N1 C1 1.333(3) . ?
N1 C5 1.338(3) . ?
N2 C12 1.371(3) . ?
N2 C15 1.441(3) . ?
N2 C16 1.445(3) . ?
N3 C23 1.359(3) . ?
N3 C26 1.453(3) . ?
N3 C27 1.452(3) . ?
C1 C2 1.393(3) . ?
C1 C17 1.484(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.383(4) . ?
C3 H3A 0.9500 . ?
C3 C4 1.381(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.384(3) . ?
C5 C6 1.486(3) . ?
C6 C7 1.388(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.401(3) . ?
C8 C9 1.461(3) . ?
C9 C10 1.402(3) . ?
C9 C14 1.401(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.368(4) . ?
C11 H11 0.9500 . ?
C11 C12 1.413(3) . ?
C12 C13 1.409(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.374(4) . ?
C14 H14 0.9500 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 C18 1.380(3) . ?
C18 H18 0.9500 . ?
C18 C19 1.416(3) . ?
C19 C20 1.460(3) . ?
C20 C21 1.405(3) . ?
C20 C25 1.397(3) . ?
C21 H21 0.9500 . ?
C21 C22 1.365(4) . ?
C22 H22 0.9500 . ?
C22 C23 1.416(3) . ?
C23 C24 1.415(3) . ?
C24 H24 0.9500 . ?
C24 C25 1.372(3) . ?
C25 H25 0.9500 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C6 O1 H1 103(2) . . ?
C17 O3 H3 101(2) . . ?
C1 N1 C5 118.8(2) . . ?
C12 N2 C15 121.0(2) . . ?
C12 N2 C16 119.8(2) . . ?
C15 N2 C16 119.0(2) . . ?
C23 N3 C26 120.1(2) . . ?
C23 N3 C27 120.8(2) . . ?
C27 N3 C26 116.6(2) . . ?
N1 C1 C2 122.4(2) . . ?
N1 C1 C17 115.5(2) . . ?
C2 C1 C17 122.1(2) . . ?
C1 C2 H2 120.8 . . ?
C3 C2 C1 118.3(2) . . ?
C3 C2 H2 120.8 . . ?
C2 C3 H3A 120.3 . . ?
C4 C3 C2 119.4(2) . . ?
C4 C3 H3A 120.3 . . ?
C3 C4 H4 120.6 . . ?
C3 C4 C5 118.7(2) . . ?
C5 C4 H4 120.6 . . ?
N1 C5 C4 122.4(2) . . ?
N1 C5 C6 115.8(2) . . ?
C4 C5 C6 121.8(2) . . ?
O1 C6 C5 116.6(2) . . ?
O1 C6 C7 122.5(2) . . ?
C7 C6 C5 120.9(2) . . ?
C6 C7 H7 119.9 . . ?
C6 C7 C8 120.1(2) . . ?
C8 C7 H7 119.9 . . ?
O2 C8 C7 119.6(2) . . ?
O2 C8 C9 117.3(2) . . ?
C7 C8 C9 123.1(2) . . ?
C10 C9 C8 122.8(2) . . ?
C14 C9 C8 120.1(2) . . ?
C14 C9 C10 117.1(2) . . ?
C9 C10 H10 119.1 . . ?
C11 C10 C9 121.8(2) . . ?
C11 C10 H10 119.1 . . ?
C10 C11 H11 119.5 . . ?
C10 C11 C12 121.0(2) . . ?
C12 C11 H11 119.5 . . ?
N2 C12 C11 121.6(2) . . ?
N2 C12 C13 121.1(2) . . ?
C13 C12 C11 117.4(2) . . ?
C12 C13 H13 119.6 . . ?
C14 C13 C12 120.8(2) . . ?
C14 C13 H13 119.6 . . ?
C9 C14 H14 119.1 . . ?
C13 C14 C9 121.9(2) . . ?
C13 C14 H14 119.1 . . ?
N2 C15 H15A 109.5 . . ?
N2 C15 H15B 109.5 . . ?
N2 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N2 C16 H16A 109.5 . . ?
N2 C16 H16B 109.5 . . ?
N2 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O3 C17 C1 117.1(2) . . ?
O3 C17 C18 123.0(2) . . ?
C18 C17 C1 119.9(2) . . ?
C17 C18 H18 119.4 . . ?
C17 C18 C19 121.2(2) . . ?
C19 C18 H18 119.4 . . ?
O4 C19 C18 120.0(2) . . ?
O4 C19 C20 119.4(2) . . ?
C18 C19 C20 120.6(2) . . ?
C21 C20 C19 121.9(2) . . ?
C25 C20 C19 121.0(2) . . ?
C25 C20 C21 117.1(2) . . ?
C20 C21 H21 119.0 . . ?
C22 C21 C20 121.9(2) . . ?
C22 C21 H21 119.0 . . ?
C21 C22 H22 119.4 . . ?
C21 C22 C23 121.1(2) . . ?
C23 C22 H22 119.4 . . ?
N3 C23 C22 120.2(2) . . ?
N3 C23 C24 122.8(2) . . ?
C24 C23 C22 116.9(2) . . ?
C23 C24 H24 119.5 . . ?
C25 C24 C23 121.0(2) . . ?
C25 C24 H24 119.5 . . ?
C20 C25 H25 119.1 . . ?
C24 C25 C20 121.9(2) . . ?
C24 C25 H25 119.1 . . ?
N3 C26 H26A 109.5 . . ?
N3 C26 H26B 109.5 . . ?
N3 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
N3 C27 H27A 109.5 . . ?
N3 C27 H27B 109.5 . . ?
N3 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1 H1 O2 0.862(10) 1.654(17) 2.469(3) 157(3) . yes
O3 H3 O4 0.860(10) 1.714(16) 2.534(3) 158(3) . yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C6 C7 C8 2.0(4) . . . . ?
O2 C8 C9 C10 -178.8(2) . . . . ?
O2 C8 C9 C14 0.8(3) . . . . ?
O3 C17 C18 C19 3.1(4) . . . . ?
O4 C19 C20 C21 -173.8(2) . . . . ?
O4 C19 C20 C25 5.9(3) . . . . ?
N1 C1 C2 C3 -2.4(4) . . . . ?
N1 C1 C17 O3 177.0(2) . . . . ?
N1 C1 C17 C18 -2.8(3) . . . . ?
N1 C5 C6 O1 -174.9(2) . . . . ?
N1 C5 C6 C7 5.1(3) . . . . ?
N2 C12 C13 C14 -176.4(2) . . . . ?
N3 C23 C24 C25 -179.1(2) . . . . ?
C1 N1 C5 C4 0.2(3) . . . . ?
C1 N1 C5 C6 -179.8(2) . . . . ?
C1 C2 C3 C4 0.9(4) . . . . ?
C1 C17 C18 C19 -177.2(2) . . . . ?
C2 C1 C17 O3 -3.9(3) . . . . ?
C2 C1 C17 C18 176.3(2) . . . . ?
C2 C3 C4 C5 1.0(4) . . . . ?
C3 C4 C5 N1 -1.6(4) . . . . ?
C3 C4 C5 C6 178.4(2) . . . . ?
C4 C5 C6 O1 5.2(3) . . . . ?
C4 C5 C6 C7 -174.9(2) . . . . ?
C5 N1 C1 C2 1.8(3) . . . . ?
C5 N1 C1 C17 -179.0(2) . . . . ?
C5 C6 C7 C8 -178.0(2) . . . . ?
C6 C7 C8 O2 -1.2(4) . . . . ?
C6 C7 C8 C9 178.3(2) . . . . ?
C7 C8 C9 C10 1.7(4) . . . . ?
C7 C8 C9 C14 -178.8(2) . . . . ?
C8 C9 C10 C11 -179.1(2) . . . . ?
C8 C9 C14 C13 178.9(2) . . . . ?
C9 C10 C11 C12 1.1(4) . . . . ?
C10 C9 C14 C13 -1.5(4) . . . . ?
C10 C11 C12 N2 176.2(2) . . . . ?
C10 C11 C12 C13 -3.2(4) . . . . ?
C11 C12 C13 C14 3.0(4) . . . . ?
C12 C13 C14 C9 -0.7(4) . . . . ?
C14 C9 C10 C11 1.3(4) . . . . ?
C15 N2 C12 C11 -5.4(4) . . . . ?
C15 N2 C12 C13 173.9(2) . . . . ?
C16 N2 C12 C11 -179.2(2) . . . . ?
C16 N2 C12 C13 0.2(4) . . . . ?
C17 C1 C2 C3 178.6(2) . . . . ?
C17 C18 C19 O4 -2.5(3) . . . . ?
C17 C18 C19 C20 177.0(2) . . . . ?
C18 C19 C20 C21 6.7(3) . . . . ?
C18 C19 C20 C25 -173.6(2) . . . . ?
C19 C20 C21 C22 -179.9(2) . . . . ?
C19 C20 C25 C24 179.9(2) . . . . ?
C20 C21 C22 C23 -0.3(4) . . . . ?
C21 C20 C25 C24 -0.4(3) . . . . ?
C21 C22 C23 N3 179.1(2) . . . . ?
C21 C22 C23 C24 0.2(3) . . . . ?
C22 C23 C24 C25 -0.2(3) . . . . ?
C23 C24 C25 C20 0.3(4) . . . . ?
C25 C20 C21 C22 0.4(3) . . . . ?
C26 N3 C23 C22 11.1(3) . . . . ?
C26 N3 C23 C24 -170.0(2) . . . . ?
C27 N3 C23 C22 172.5(2) . . . . ?
C27 N3 C23 C24 -8.6(3) . . . . ?

_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_21wdb05
_database_code_depnum_ccdc_archive 'CCDC 2479264'
loop_
_audit_author_name
_audit_author_address
'Kraig Wheeler'
;Whitworth University
United States of America
;
_audit_update_record             
;
2025-08-08 deposited with the CCDC.	2025-10-31 downloaded from the CCDC.
;
# JA-1-007

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C16 H16 N4'
_chemical_formula_sum            'C16 H16 N4'
_chemical_formula_weight         264.33

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

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

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

_cell_length_a                   11.5707(3)
_cell_length_b                   6.0057(2)
_cell_length_c                   19.0933(6)
_cell_angle_alpha                90
_cell_angle_beta                 98.018(1)
_cell_angle_gamma                90
_cell_volume                     1313.83(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9925
_cell_measurement_theta_min      3.86
_cell_measurement_theta_max      71.81
_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_min          0.038
_exptl_crystal_size_mid          0.186
_exptl_crystal_size_max          0.205
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.336
_exptl_crystal_F_000             560
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_absorpt_coefficient_mu    0.652
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?

_exptl_absorpt_correction_T_min  0.6548
_exptl_absorpt_correction_T_max  0.7536
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Bruker AXS)
Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10.
;

_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_type           CuK\a
_diffrn_source                   'Microsource IuS Incoatec 3.0'
_diffrn_detector                 'Bruker Photon II CPAD'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'CPAD Area Detector'
_diffrn_measurement_device       'Kappa Four-Circle Diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  'Double Bounce Multilayer Mirrors'
_diffrn_radiation_probe          X-ray

_diffrn_reflns_number            23491
_diffrn_reflns_av_unetI/netI     0.0217
_diffrn_reflns_av_R_equivalents  0.0418
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         3.858
_diffrn_reflns_theta_max         72.005
_diffrn_reflns_theta_full        67.679
_diffrn_measured_fraction_theta_max 0.995
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.995
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.995
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             2580
_reflns_number_gt                2291
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'APEX3 v2018.7-2 (Bruker, 2018)'
_computing_cell_refinement       'SAINT V8.38A (Bruker, 2017)'
_computing_data_reduction        'SAINT V8.38A (Bruker, 2017)'
_computing_structure_solution    'SHELXT-2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'XSEED (Barbour, 2001)'
_computing_publication_material  'XSEED (Barbour, 2001)'

_refine_special_details          
;
All nonhydrogen atoms were located in a single difference Fourier electron
 density map and refined using anisotropic displacement parameters. All C-H
 hydrogen atoms were placed in calculated positions with Uiso = 1.2xUeqiv
 of the connected C atoms (1.5xUeqiv for methyl groups). The H atom
 attached to nitrogen was located in Fourier diff maps
 and assigned Uiso = 1.2xUeqiv.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0494P)²+0.5421P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     intrinsic
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2580
_refine_ls_number_parameters     186
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0415
_refine_ls_R_factor_gt           0.0366
_refine_ls_wR_factor_ref         0.0982
_refine_ls_wR_factor_gt          0.0942
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.049
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.62023(8) 0.25244(17) 0.50997(5) 0.0188(2) Uani 1 1 d . . . . .
N2 N 0.45672(9) 0.12074(17) 0.59638(5) 0.0194(2) Uani 1 1 d . . . . .
HN2 H 0.4608(12) 0.023(3) 0.5613(8) 0.023 Uiso 1 1 d . U . . .
N3 N 0.37371(9) 0.09371(17) 0.63927(5) 0.0206(2) Uani 1 1 d . . . . .
N4 N 0.03874(9) 0.43233(17) 0.86149(6) 0.0229(2) Uani 1 1 d . . . . .
C1 C 0.69648(10) 0.3216(2) 0.46773(6) 0.0204(3) Uani 1 1 d . . . . .
H1 H 0.710950 0.227025 0.430031 0.024 Uiso 1 1 calc R U . . .
C2 C 0.75553(10) 0.5233(2) 0.47589(6) 0.0203(3) Uani 1 1 d . . . . .
H2 H 0.808819 0.564959 0.444590 0.024 Uiso 1 1 calc R U . . .
C3 C 0.73497(10) 0.6624(2) 0.53064(6) 0.0212(3) Uani 1 1 d . . . . .
H3 H 0.773404 0.802090 0.537378 0.025 Uiso 1 1 calc R U . . .
C4 C 0.65730(10) 0.5942(2) 0.57548(6) 0.0198(3) Uani 1 1 d . . . . .
H4 H 0.642346 0.685633 0.613808 0.024 Uiso 1 1 calc R U . . .
C5 C 0.60144(10) 0.3889(2) 0.56340(6) 0.0172(3) Uani 1 1 d . . . . .
C6 C 0.51480(10) 0.3157(2) 0.60774(6) 0.0176(3) Uani 1 1 d . . . . .
C7 C 0.46968(10) 0.4206(2) 0.66235(6) 0.0178(2) Uani 1 1 d . . . . .
H7 H 0.493197 0.559308 0.683673 0.021 Uiso 1 1 calc R U . . .
C8 C 0.38128(10) 0.2777(2) 0.67963(6) 0.0179(3) Uani 1 1 d . . . . .
C9 C 0.29671(10) 0.3145(2) 0.72929(6) 0.0171(3) Uani 1 1 d . . . . .
C10 C 0.29177(10) 0.5165(2) 0.76515(6) 0.0194(3) Uani 1 1 d . . . . .
H10 H 0.347363 0.629182 0.759490 0.023 Uiso 1 1 calc R U . . .
C11 C 0.20767(10) 0.5566(2) 0.80879(6) 0.0200(3) Uani 1 1 d . . . . .
H11 H 0.206815 0.695596 0.832456 0.024 Uiso 1 1 calc R U . . .
C12 C 0.12355(10) 0.39419(19) 0.81853(6) 0.0174(3) Uani 1 1 d . . . . .
C13 C 0.12924(11) 0.1903(2) 0.78270(6) 0.0200(3) Uani 1 1 d . . . . .
H13 H 0.074179 0.076679 0.788326 0.024 Uiso 1 1 calc R U . . .
C14 C 0.21363(11) 0.1530(2) 0.73948(6) 0.0197(3) Uani 1 1 d . . . . .
H14 H 0.215251 0.013759 0.716046 0.024 Uiso 1 1 calc R U . . .
C15 C -0.03639(11) 0.2540(2) 0.87867(7) 0.0246(3) Uani 1 1 d . . . . .
H15A H -0.075434 0.186552 0.834932 0.037 Uiso 1 1 calc R U . . .
H15B H -0.095080 0.313664 0.905987 0.037 Uiso 1 1 calc R U . . .
H15C H 0.010417 0.140974 0.906730 0.037 Uiso 1 1 calc R U . . .
C16 C 0.03497(12) 0.6418(2) 0.89798(7) 0.0276(3) Uani 1 1 d . . . . .
H16A H 0.107329 0.661568 0.930748 0.041 Uiso 1 1 calc R U . . .
H16B H -0.031690 0.642655 0.924511 0.041 Uiso 1 1 calc R U . . .
H16C H 0.026690 0.763623 0.863490 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
N1 C1 1.3415(15) . ?
N1 C5 1.3498(15) . ?
N2 C6 1.3526(16) . ?
N2 N3 1.3560(14) . ?
N2 HN2 0.895(16) . ?
N3 C8 1.3432(15) . ?
N4 C12 1.3830(15) . ?
N4 C16 1.4418(16) . ?
N4 C15 1.4455(16) . ?
C1 C2 1.3890(18) . ?
C1 H1 0.9500 . ?
C2 C3 1.3842(17) . ?
C2 H2 0.9500 . ?
C3 C4 1.3869(17) . ?
C3 H3 0.9500 . ?
C4 C5 1.3959(17) . ?
C4 H4 0.9500 . ?
C5 C6 1.4668(16) . ?
C6 C7 1.3815(16) . ?
C7 C8 1.4091(16) . ?
C7 H7 0.9500 . ?
C8 C9 1.4712(15) . ?
C9 C10 1.3980(16) . ?
C9 C14 1.3983(17) . ?
C10 C11 1.3876(16) . ?
C10 H10 0.9500 . ?
C11 C12 1.4083(17) . ?
C11 H11 0.9500 . ?
C12 C13 1.4086(17) . ?
C13 C14 1.3817(17) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C5 117.07(10) . . ?
C6 N2 N3 112.63(10) . . ?
C6 N2 HN2 127.5(10) . . ?
N3 N2 HN2 119.3(9) . . ?
C8 N3 N2 104.65(10) . . ?
C12 N4 C16 120.19(10) . . ?
C12 N4 C15 120.72(10) . . ?
C16 N4 C15 118.49(10) . . ?
N1 C1 C2 123.86(11) . . ?
N1 C1 H1 118.1 . . ?
C2 C1 H1 118.1 . . ?
C3 C2 C1 118.50(11) . . ?
C3 C2 H2 120.8 . . ?
C1 C2 H2 120.8 . . ?
C2 C3 C4 118.85(11) . . ?
C2 C3 H3 120.6 . . ?
C4 C3 H3 120.6 . . ?
C3 C4 C5 118.93(11) . . ?
C3 C4 H4 120.5 . . ?
C5 C4 H4 120.5 . . ?
N1 C5 C4 122.78(11) . . ?
N1 C5 C6 116.70(10) . . ?
C4 C5 C6 120.47(11) . . ?
N2 C6 C7 106.51(10) . . ?
N2 C6 C5 122.09(10) . . ?
C7 C6 C5 131.27(11) . . ?
C6 C7 C8 105.19(10) . . ?
C6 C7 H7 127.4 . . ?
C8 C7 H7 127.4 . . ?
N3 C8 C7 110.99(10) . . ?
N3 C8 C9 119.83(10) . . ?
C7 C8 C9 128.99(11) . . ?
C10 C9 C14 117.26(11) . . ?
C10 C9 C8 121.49(11) . . ?
C14 C9 C8 121.16(11) . . ?
C11 C10 C9 121.63(11) . . ?
C11 C10 H10 119.2 . . ?
C9 C10 H10 119.2 . . ?
C10 C11 C12 120.98(11) . . ?
C10 C11 H11 119.5 . . ?
C12 C11 H11 119.5 . . ?
N4 C12 C11 121.62(11) . . ?
N4 C12 C13 121.14(11) . . ?
C11 C12 C13 117.24(10) . . ?
C14 C13 C12 121.05(11) . . ?
C14 C13 H13 119.5 . . ?
C12 C13 H13 119.5 . . ?
C13 C14 C9 121.83(11) . . ?
C13 C14 H14 119.1 . . ?
C9 C14 H14 119.1 . . ?
N4 C15 H15A 109.5 . . ?
N4 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N4 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N4 C16 H16A 109.5 . . ?
N4 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
N4 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 N2 N3 C8 -0.80(13) . . . . ?
C5 N1 C1 C2 -0.32(17) . . . . ?
N1 C1 C2 C3 -0.05(18) . . . . ?
C1 C2 C3 C4 0.59(17) . . . . ?
C2 C3 C4 C5 -0.76(17) . . . . ?
C1 N1 C5 C4 0.13(17) . . . . ?
C1 N1 C5 C6 177.85(10) . . . . ?
C3 C4 C5 N1 0.40(17) . . . . ?
C3 C4 C5 C6 -177.23(11) . . . . ?
N3 N2 C6 C7 1.57(13) . . . . ?
N3 N2 C6 C5 -174.69(10) . . . . ?
N1 C5 C6 N2 0.43(16) . . . . ?
C4 C5 C6 N2 178.20(11) . . . . ?
N1 C5 C6 C7 -174.80(12) . . . . ?
C4 C5 C6 C7 2.98(19) . . . . ?
N2 C6 C7 C8 -1.62(12) . . . . ?
C5 C6 C7 C8 174.17(12) . . . . ?
N2 N3 C8 C7 -0.29(13) . . . . ?
N2 N3 C8 C9 175.09(10) . . . . ?
C6 C7 C8 N3 1.21(13) . . . . ?
C6 C7 C8 C9 -173.63(11) . . . . ?
N3 C8 C9 C10 -171.31(11) . . . . ?
C7 C8 C9 C10 3.14(18) . . . . ?
N3 C8 C9 C14 5.05(17) . . . . ?
C7 C8 C9 C14 179.49(12) . . . . ?
C14 C9 C10 C11 -0.37(17) . . . . ?
C8 C9 C10 C11 176.12(11) . . . . ?
C9 C10 C11 C12 -0.10(18) . . . . ?
C16 N4 C12 C11 -0.29(17) . . . . ?
C15 N4 C12 C11 -171.32(11) . . . . ?
C16 N4 C12 C13 179.65(11) . . . . ?
C15 N4 C12 C13 8.62(17) . . . . ?
C10 C11 C12 N4 -179.56(11) . . . . ?
C10 C11 C12 C13 0.50(17) . . . . ?
N4 C12 C13 C14 179.63(11) . . . . ?
C11 C12 C13 C14 -0.43(17) . . . . ?
C12 C13 C14 C9 -0.04(18) . . . . ?
C10 C9 C14 C13 0.44(17) . . . . ?
C8 C9 C14 C13 -176.06(11) . . . . ?

_refine_diff_density_max         0.174
_refine_diff_density_min         -0.248
_refine_diff_density_rms         0.043

####################################################################### 
# 
# 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_cu_sci22_06_0m_5
_database_code_depnum_ccdc_archive 'CCDC 2479266'
loop_
_audit_author_name
_audit_author_address
'Kraig Wheeler'
;Whitworth University
United States of America
;
_audit_update_record             
;
2025-08-08 deposited with the CCDC.	2025-10-31 downloaded from the CCDC.
;
_audit_creation_date             2025-07-24
_audit_creation_method           
;
Olex2 1.5
(compiled 2025.07.13 svn.rb7424aed for OlexSys, GUI svn.r7308)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C27 H27 N3 O4'
_chemical_formula_sum            'C27 H27 N3 O4'
_chemical_formula_weight         457.51
_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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   8.1741(9)
_cell_length_b                   10.6497(12)
_cell_length_c                   26.131(3)
_cell_angle_alpha                90
_cell_angle_beta                 96.891(4)
_cell_angle_gamma                90
_cell_volume                     2258.3(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5479
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      69.79
_cell_measurement_theta_min      4.48
_shelx_estimated_absorpt_T_max   0.978
_shelx_estimated_absorpt_T_min   0.820
_exptl_absorpt_coefficient_mu    0.740
_exptl_absorpt_correction_T_max  0.753295
_exptl_absorpt_correction_T_min  0.576506
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Krause et al., 2015) was used for absorption correction.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.346
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             968
_exptl_crystal_size_max          0.28
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.03
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0792
_diffrn_reflns_av_unetI/netI     0.0574
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            4380
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.986
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.054
_diffrn_reflns_theta_min         3.407
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 '100 \\times 140 mm^2^ CMOS sensor'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'Bruker PHOTON II'
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device       'κ-geometry four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_collimation    'focusing mirror'
_diffrn_radiation_detector       'Bruker PHOTON II'
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.1
_diffrn_source_power             0.05500000000000001
_diffrn_source_type              'Incoatec I\mS 3.0'
_diffrn_source_voltage           50.0
_diffrn_standards_number         .
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3020
_reflns_number_total             4380
_reflns_special_details          
;
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT+ V8.40B (Bruker AXS Inc., 2020)'
_computing_data_collection       'APEX3 Ver.2019.11-0 (Bruker-AXS, 2019)'
_computing_data_reduction        'SAINT+ Ve8.40B (Bruker-AXS, 2020)'
_computing_molecular_graphics    'OLEX2 (Dolomanov et al., 2009)'
_computing_publication_material  'OLEX2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2019/1)'
_computing_structure_solution    'XT (Sheldrick, 2018/2)'
_refine_diff_density_max         0.293
_refine_diff_density_min         -0.359
_refine_diff_density_rms         0.080
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.086
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     312
_refine_ls_number_reflns         4380
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.1374
_refine_ls_R_factor_gt           0.0896
_refine_ls_restrained_S_all      1.086
_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)+(0.0506P)²+5.7237P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1801
_refine_ls_wR_factor_ref         0.2120
_refine_special_details          
;
All nonhydrogen atoms were located in a single difference Fourier 
electron density map and refined using anisotropic displacement 
parameters. All C-H hydrogen atoms were placed in calculated 
positions with Uiso = 1.2xUeqiv of the connected C atoms 
(1.5xUeqiv for methyl groups). Those H atoms attached to oxygen were located in Fourier diff mapsand assigned Uiso =
The structure exhibits twinning and was 
refined hklf5 data.  
1.5xUeqiv for NH groups.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.856(6)
 0.144(6)
2. 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, All O(H) groups
3. Restrained distances
 O2-H2
 0.85 with sigma of 0.01
4.a Secondary CH2 refined with riding coordinates:
 C18(H18A,H18B)
4.b Aromatic/amide H refined with riding coordinates:
 C2(H2A), C3(H3), C4(H4), C7(H7), C10(H10), C11(H11), C13(H13), C14(H14),
 C21(H21), C22(H22), C24(H24), C25(H25)
4.c Tetrahedral OH refined with riding coordinates:
 O2(H2)
4.d Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C26(H26A,H26B,H26C), C27(H27A,H27B,
 H27C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     intrinsic
_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
O1 O -0.1766(4) -0.2891(3) -0.34859(10) 0.0389(7) Uani 1 1 d . . . . .
O2 O -0.1025(4) -0.2463(3) -0.43422(10) 0.0389(7) Uani 1 1 d D . . . .
H2 H -0.128685 -0.231768 -0.404674 0.058 Uiso 1 1 calc DR U . . .
O3 O -0.5786(4) -0.8531(3) -0.30481(11) 0.0456(8) Uani 1 1 d . . . . .
O4 O -0.2668(4) -0.8900(3) -0.37284(10) 0.0416(8) Uani 1 1 d . . . . .
N1 N -0.3804(4) -0.5836(3) -0.34575(11) 0.0294(8) Uani 1 1 d . . . . .
N2 N -0.1129(5) -0.4447(4) -0.66191(13) 0.0472(10) Uani 1 1 d . . . . .
N3 N -0.2971(5) -0.8965(4) -0.61839(13) 0.0428(10) Uani 1 1 d . . . . .
C1 C -0.4397(5) -0.6602(4) -0.31160(14) 0.0311(9) Uani 1 1 d . . . . .
C2 C -0.4285(5) -0.6356(4) -0.25891(14) 0.0334(10) Uani 1 1 d . . . . .
H2A H -0.471491 -0.693029 -0.236110 0.040 Uiso 1 1 calc R U . . .
C3 C -0.3531(5) -0.5252(4) -0.24069(15) 0.0354(10) Uani 1 1 d . . . . .
H3 H -0.343201 -0.505201 -0.205017 0.042 Uiso 1 1 calc R U . . .
C4 C -0.2921(5) -0.4441(4) -0.27562(15) 0.0355(10) Uani 1 1 d . . . . .
H4 H -0.240712 -0.367416 -0.264193 0.043 Uiso 1 1 calc R U . . .
C5 C -0.3074(5) -0.4771(4) -0.32774(14) 0.0312(9) Uani 1 1 d . . . . .
C6 C -0.2388(5) -0.3951(4) -0.36592(14) 0.0325(9) Uani 1 1 d . . . . .
C7 C -0.2404(5) -0.4309(4) -0.41708(14) 0.0319(9) Uani 1 1 d . . . . .
H7 H -0.290904 -0.507552 -0.428997 0.038 Uiso 1 1 calc R U . . .
C8 C -0.1665(5) -0.3528(4) -0.45098(14) 0.0316(9) Uani 1 1 d . . . . .
C9 C -0.1549(5) -0.3803(4) -0.50540(14) 0.0317(9) Uani 1 1 d . . . . .
C10 C -0.0668(5) -0.2995(4) -0.53356(15) 0.0345(10) Uani 1 1 d . . . . .
H10 H -0.014532 -0.228473 -0.516757 0.041 Uiso 1 1 calc R U . . .
C11 C -0.0522(5) -0.3186(5) -0.58498(15) 0.0378(10) Uani 1 1 d . . . . .
H11 H 0.008783 -0.261123 -0.603037 0.045 Uiso 1 1 calc R U . . .
C12 C -0.1275(5) -0.4230(5) -0.61058(15) 0.0371(10) Uani 1 1 d . . . . .
C13 C -0.2156(6) -0.5057(4) -0.58242(15) 0.0383(10) Uani 1 1 d . . . . .
H13 H -0.267367 -0.577061 -0.599143 0.046 Uiso 1 1 calc R U . . .
C14 C -0.2287(5) -0.4856(4) -0.53065(15) 0.0344(10) Uani 1 1 d . . . . .
H14 H -0.287907 -0.543539 -0.512232 0.041 Uiso 1 1 calc R U . . .
C15 C -0.1912(6) -0.5538(6) -0.68772(17) 0.0543(14) Uani 1 1 d . . . . .
H15A H -0.155907 -0.629705 -0.668272 0.081 Uiso 1 1 calc R U . . .
H15B H -0.159299 -0.559855 -0.722613 0.081 Uiso 1 1 calc R U . . .
H15C H -0.311154 -0.545308 -0.689692 0.081 Uiso 1 1 calc R U . . .
C16 C -0.0470(7) -0.3478(6) -0.69293(17) 0.0561(15) Uani 1 1 d . . . . .
H16A H 0.053151 -0.312472 -0.673974 0.084 Uiso 1 1 calc R U . . .
H16B H -0.129173 -0.281239 -0.700379 0.084 Uiso 1 1 calc R U . . .
H16C H -0.020692 -0.384540 -0.725347 0.084 Uiso 1 1 calc R U . . .
C17 C -0.5218(5) -0.7775(4) -0.33308(15) 0.0326(9) Uani 1 1 d . . . . .
C18 C -0.5323(5) -0.7981(4) -0.39071(14) 0.0330(9) Uani 1 1 d . . . . .
H18A H -0.625417 -0.855162 -0.401810 0.040 Uiso 1 1 calc R U . . .
H18B H -0.554308 -0.716872 -0.408652 0.040 Uiso 1 1 calc R U . . .
C19 C -0.3755(5) -0.8537(4) -0.40596(15) 0.0324(9) Uani 1 1 d . . . . .
C20 C -0.3595(5) -0.8663(4) -0.46139(14) 0.0298(9) Uani 1 1 d . . . . .
C21 C -0.4663(5) -0.8066(4) -0.49927(16) 0.0369(10) Uani 1 1 d . . . . .
H21 H -0.554434 -0.757623 -0.489385 0.044 Uiso 1 1 calc R U . . .
C22 C -0.4470(6) -0.8171(4) -0.55101(15) 0.0379(10) Uani 1 1 d . . . . .
H22 H -0.522015 -0.775464 -0.575996 0.045 Uiso 1 1 calc R U . . .
C23 C -0.3183(5) -0.8882(4) -0.56694(14) 0.0324(9) Uani 1 1 d . . . . .
C24 C -0.2139(5) -0.9518(4) -0.52926(15) 0.0364(10) Uani 1 1 d . . . . .
H24 H -0.127851 -1.002997 -0.539100 0.044 Uiso 1 1 calc R U . . .
C25 C -0.2352(5) -0.9405(4) -0.47776(16) 0.0356(10) Uani 1 1 d . . . . .
H25 H -0.162939 -0.984626 -0.452790 0.043 Uiso 1 1 calc R U . . .
C26 C -0.1531(6) -0.9559(5) -0.63514(16) 0.0441(12) Uani 1 1 d . . . . .
H26A H -0.053662 -0.924260 -0.614441 0.066 Uiso 1 1 calc R U . . .
H26B H -0.147772 -0.936441 -0.671563 0.066 Uiso 1 1 calc R U . . .
H26C H -0.160318 -1.047003 -0.630741 0.066 Uiso 1 1 calc R U . . .
C27 C -0.4235(7) -0.8492(5) -0.65728(16) 0.0527(14) Uani 1 1 d . . . . .
H27A H -0.433205 -0.758014 -0.653497 0.079 Uiso 1 1 calc R U . . .
H27B H -0.529142 -0.888921 -0.653019 0.079 Uiso 1 1 calc R U . . .
H27C H -0.393565 -0.868559 -0.691624 0.079 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 1.297(5) . ?
O2 H2 0.8400 . ?
O2 C8 1.303(5) . ?
O3 C17 1.221(5) . ?
O4 C19 1.226(5) . ?
N1 C1 1.342(5) . ?
N1 C5 1.340(5) . ?
N2 C12 1.380(5) . ?
N2 C15 1.453(7) . ?
N2 C16 1.454(6) . ?
N3 C23 1.379(5) . ?
N3 C26 1.450(6) . ?
N3 C27 1.450(6) . ?
C1 C2 1.394(5) . ?
C1 C17 1.496(6) . ?
C2 H2A 0.9500 . ?
C2 C3 1.385(6) . ?
C3 H3 0.9500 . ?
C3 C4 1.392(6) . ?
C4 H4 0.9500 . ?
C4 C5 1.397(5) . ?
C5 C6 1.486(5) . ?
C6 C7 1.389(5) . ?
C7 H7 0.9500 . ?
C7 C8 1.404(6) . ?
C8 C9 1.466(5) . ?
C9 C10 1.389(6) . ?
C9 C14 1.401(6) . ?
C10 H10 0.9500 . ?
C10 C11 1.378(5) . ?
C11 H11 0.9500 . ?
C11 C12 1.401(6) . ?
C12 C13 1.401(6) . ?
C13 H13 0.9500 . ?
C13 C14 1.386(5) . ?
C14 H14 0.9500 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 C18 1.514(5) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C18 C19 1.508(6) . ?
C19 C20 1.476(5) . ?
C20 C21 1.393(6) . ?
C20 C25 1.394(6) . ?
C21 H21 0.9500 . ?
C21 C22 1.384(6) . ?
C22 H22 0.9500 . ?
C22 C23 1.400(6) . ?
C23 C24 1.398(6) . ?
C24 H24 0.9500 . ?
C24 C25 1.383(6) . ?
C25 H25 0.9500 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C8 O2 H2 109.5 . . ?
C5 N1 C1 117.5(3) . . ?
C12 N2 C15 120.0(4) . . ?
C12 N2 C16 120.3(4) . . ?
C15 N2 C16 118.7(4) . . ?
C23 N3 C26 121.6(4) . . ?
C23 N3 C27 119.9(4) . . ?
C26 N3 C27 118.4(3) . . ?
N1 C1 C2 123.8(4) . . ?
N1 C1 C17 116.1(3) . . ?
C2 C1 C17 120.1(4) . . ?
C1 C2 H2A 120.9 . . ?
C3 C2 C1 118.2(4) . . ?
C3 C2 H2A 120.9 . . ?
C2 C3 H3 120.6 . . ?
C2 C3 C4 118.7(4) . . ?
C4 C3 H3 120.6 . . ?
C3 C4 H4 120.5 . . ?
C3 C4 C5 119.1(4) . . ?
C5 C4 H4 120.5 . . ?
N1 C5 C4 122.6(4) . . ?
N1 C5 C6 116.7(3) . . ?
C4 C5 C6 120.7(4) . . ?
O1 C6 C5 116.1(3) . . ?
O1 C6 C7 122.3(4) . . ?
C7 C6 C5 121.6(4) . . ?
C6 C7 H7 120.3 . . ?
C6 C7 C8 119.3(4) . . ?
C8 C7 H7 120.3 . . ?
O2 C8 C7 119.3(3) . . ?
O2 C8 C9 115.5(4) . . ?
C7 C8 C9 125.2(4) . . ?
C10 C9 C8 119.2(4) . . ?
C10 C9 C14 117.9(4) . . ?
C14 C9 C8 122.9(4) . . ?
C9 C10 H10 118.8 . . ?
C11 C10 C9 122.4(4) . . ?
C11 C10 H10 118.8 . . ?
C10 C11 H11 120.1 . . ?
C10 C11 C12 119.9(4) . . ?
C12 C11 H11 120.1 . . ?
N2 C12 C11 120.8(4) . . ?
N2 C12 C13 121.0(4) . . ?
C11 C12 C13 118.2(4) . . ?
C12 C13 H13 119.3 . . ?
C14 C13 C12 121.3(4) . . ?
C14 C13 H13 119.3 . . ?
C9 C14 H14 119.9 . . ?
C13 C14 C9 120.3(4) . . ?
C13 C14 H14 119.9 . . ?
N2 C15 H15A 109.5 . . ?
N2 C15 H15B 109.5 . . ?
N2 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N2 C16 H16A 109.5 . . ?
N2 C16 H16B 109.5 . . ?
N2 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
O3 C17 C1 120.7(4) . . ?
O3 C17 C18 121.7(4) . . ?
C1 C17 C18 117.6(3) . . ?
C17 C18 H18A 109.3 . . ?
C17 C18 H18B 109.3 . . ?
H18A C18 H18B 107.9 . . ?
C19 C18 C17 111.8(3) . . ?
C19 C18 H18A 109.3 . . ?
C19 C18 H18B 109.3 . . ?
O4 C19 C18 120.3(3) . . ?
O4 C19 C20 121.5(4) . . ?
C20 C19 C18 118.2(4) . . ?
C21 C20 C19 122.3(4) . . ?
C21 C20 C25 117.3(4) . . ?
C25 C20 C19 120.4(4) . . ?
C20 C21 H21 119.3 . . ?
C22 C21 C20 121.5(4) . . ?
C22 C21 H21 119.3 . . ?
C21 C22 H22 119.6 . . ?
C21 C22 C23 120.8(4) . . ?
C23 C22 H22 119.6 . . ?
N3 C23 C22 120.8(4) . . ?
N3 C23 C24 121.2(4) . . ?
C24 C23 C22 118.0(4) . . ?
C23 C24 H24 119.8 . . ?
C25 C24 C23 120.4(4) . . ?
C25 C24 H24 119.8 . . ?
C20 C25 H25 119.0 . . ?
C24 C25 C20 121.9(4) . . ?
C24 C25 H25 119.0 . . ?
N3 C26 H26A 109.5 . . ?
N3 C26 H26B 109.5 . . ?
N3 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
N3 C27 H27A 109.5 . . ?
N3 C27 H27B 109.5 . . ?
N3 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C6 C7 C8 2.7(7) . . . . ?
O2 C8 C9 C10 5.6(6) . . . . ?
O2 C8 C9 C14 -174.8(4) . . . . ?
O3 C17 C18 C19 -97.4(5) . . . . ?
O4 C19 C20 C21 -168.4(4) . . . . ?
O4 C19 C20 C25 12.0(6) . . . . ?
N1 C1 C2 C3 0.6(6) . . . . ?
N1 C1 C17 O3 179.6(4) . . . . ?
N1 C1 C17 C18 -0.7(6) . . . . ?
N1 C5 C6 O1 176.3(4) . . . . ?
N1 C5 C6 C7 -4.1(6) . . . . ?
N2 C12 C13 C14 179.0(4) . . . . ?
N3 C23 C24 C25 178.8(4) . . . . ?
C1 N1 C5 C4 -0.2(6) . . . . ?
C1 N1 C5 C6 178.5(4) . . . . ?
C1 C2 C3 C4 0.0(6) . . . . ?
C1 C17 C18 C19 82.8(5) . . . . ?
C2 C1 C17 O3 -0.6(6) . . . . ?
C2 C1 C17 C18 179.1(4) . . . . ?
C2 C3 C4 C5 -0.6(6) . . . . ?
C3 C4 C5 N1 0.7(7) . . . . ?
C3 C4 C5 C6 -177.9(4) . . . . ?
C4 C5 C6 O1 -5.0(6) . . . . ?
C4 C5 C6 C7 174.5(4) . . . . ?
C5 N1 C1 C2 -0.5(6) . . . . ?
C5 N1 C1 C17 179.4(4) . . . . ?
C5 C6 C7 C8 -176.8(4) . . . . ?
C6 C7 C8 O2 -2.2(6) . . . . ?
C6 C7 C8 C9 178.2(4) . . . . ?
C7 C8 C9 C10 -174.8(4) . . . . ?
C7 C8 C9 C14 4.9(7) . . . . ?
C8 C9 C10 C11 -179.3(4) . . . . ?
C8 C9 C14 C13 179.0(4) . . . . ?
C9 C10 C11 C12 -0.3(7) . . . . ?
C10 C9 C14 C13 -1.3(6) . . . . ?
C10 C11 C12 N2 -179.2(4) . . . . ?
C10 C11 C12 C13 -0.3(6) . . . . ?
C11 C12 C13 C14 0.1(7) . . . . ?
C12 C13 C14 C9 0.8(7) . . . . ?
C14 C9 C10 C11 1.1(6) . . . . ?
C15 N2 C12 C11 179.7(4) . . . . ?
C15 N2 C12 C13 0.8(7) . . . . ?
C16 N2 C12 C11 -12.0(7) . . . . ?
C16 N2 C12 C13 169.1(4) . . . . ?
C17 C1 C2 C3 -179.3(4) . . . . ?
C17 C18 C19 O4 8.5(6) . . . . ?
C17 C18 C19 C20 -173.4(4) . . . . ?
C18 C19 C20 C21 13.4(6) . . . . ?
C18 C19 C20 C25 -166.2(4) . . . . ?
C19 C20 C21 C22 178.4(4) . . . . ?
C19 C20 C25 C24 -178.2(4) . . . . ?
C20 C21 C22 C23 -0.2(7) . . . . ?
C21 C20 C25 C24 2.1(6) . . . . ?
C21 C22 C23 N3 -178.7(4) . . . . ?
C21 C22 C23 C24 2.2(7) . . . . ?
C22 C23 C24 C25 -2.1(6) . . . . ?
C23 C24 C25 C20 -0.1(7) . . . . ?
C25 C20 C21 C22 -2.0(7) . . . . ?
C26 N3 C23 C22 171.9(4) . . . . ?
C26 N3 C23 C24 -9.1(7) . . . . ?
C27 N3 C23 C22 -10.3(7) . . . . ?
C27 N3 C23 C24 168.7(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.856(6)
2 0.144(6)

####################################################################### 
# 
# 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_25wdb02
_database_code_depnum_ccdc_archive 'CCDC 2479268'
loop_
_audit_author_name
_audit_author_address
'Kraig Wheeler'
;Whitworth University
United States of America
;
_audit_update_record             
;
2025-08-08 deposited with the CCDC.	2025-10-31 downloaded from the CCDC.
;
_audit_creation_date             2025-07-24
_audit_creation_method           
;
Olex2 1.5
(compiled 2025.07.13 svn.rb7424aed for OlexSys, GUI svn.r7308)
;
_shelx_SHELXL_version_number     2019/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C27 H27 Cl2 N7 Zn, 2(C3 H7 N O)'
_chemical_formula_sum            'C33 H41 Cl2 N9 O2 Zn'
_chemical_formula_weight         732.02
_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'
Cl Cl 0.3639 0.7018 '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'
Zn Zn -1.5491 0.6778 '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           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
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                   13.2533(3)
_cell_length_b                   11.8894(3)
_cell_length_c                   23.1759(5)
_cell_angle_alpha                90
_cell_angle_beta                 105.245(2)
_cell_angle_gamma                90
_cell_volume                     3523.40(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    9952
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      72.30
_cell_measurement_theta_min      3.95
_shelx_estimated_absorpt_T_max   0.921
_shelx_estimated_absorpt_T_min   0.586
_exptl_absorpt_coefficient_mu    2.717
_exptl_absorpt_correction_T_max  0.7402
_exptl_absorpt_correction_T_min  0.6441
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 (Krause et al., 2015) was used for absorption correction.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.380
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             1528
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1.00 1.00 -1.00 0.0990
-1.00 0.00 1.00 0.0090
0.00 -1.00 0.00 0.1100
0.00 1.00 0.00 0.0720
0.00 1.00 1.00 0.0770
0.00 0.00 1.00 0.0540
0.00 0.00 -1.00 0.0710
1.00 -1.00 1.00 0.0520
1.00 0.00 -1.00 0.0120

_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.154
_exptl_crystal_size_min          0.031
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0866
_diffrn_reflns_av_unetI/netI     0.0387
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            64548
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.679
_diffrn_reflns_theta_max         72.296
_diffrn_reflns_theta_min         3.501
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 '100 \\times 140 mm^2^ CMOS sensor'
_diffrn_detector_area_resol_mean 7.9
_diffrn_detector_type            'Bruker PHOTON II'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device       'κ-geometry four-circle diffractometer'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_radiation_collimation    'focusing mirror'
_diffrn_radiation_detector       'Bruker PHOTON II'
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_radiation_probe          X-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_radiation_xray_symbol    K-L~3~
_diffrn_source                   'microfocus sealed X-ray tube'
_diffrn_source_current           1.1
_diffrn_source_power             0.05500000000000001
_diffrn_source_type              'Incoatec I\mS 3.0'
_diffrn_source_voltage           50.0
_diffrn_standards_number         .
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5709
_reflns_number_total             6948
_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+ V8.40B (Bruker AXS Inc., 2020)'
_computing_data_collection       'APEX3 Ver.2019.11-0 (Bruker-AXS, 2019)'
_computing_data_reduction        'SAINT+ Ve8.40B (Bruker-AXS, 2020)'
_computing_molecular_graphics    'OLEX2 (Dolomanov et al., 2009)'
_computing_publication_material  'OLEX2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2019/1)'
_computing_structure_solution    'XT (Sheldrick, 2018/2)'
_refine_diff_density_max         0.372
_refine_diff_density_min         -0.487
_refine_diff_density_rms         0.078
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     438
_refine_ls_number_reflns         6948
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0627
_refine_ls_R_factor_gt           0.0462
_refine_ls_restrained_S_all      1.064
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0453P)²+6.2782P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1047
_refine_ls_wR_factor_ref         0.1154
_refine_special_details          
;
All nonhydrogen atoms were located in a single difference Fourier 
electron density map and refined using anisotropic displacement 
parameters. All C-H hydrogen atoms were placed in calculated 
positions with Uiso = 1.2xUeqiv of the connected C atoms 
(1.5xUeqiv for methyl groups). Those H atoms attached to nitrogen 
were located in Fourier diff mapsand assigned Uiso = 
1.2xUeqiv for NH groups.
;
_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.a Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3A), C4(H4), C7(H7), C10(H10), C11(H11), C13(H13), C14(H14),
 C18(H18), C21(H21), C22(H22), C24(H24), C25(H25), C28(H28), C31(H31)
2.b Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C), C16(H16A,H16B,H16C), C26(H26A,H26B,H26C), C27(H27A,H27B,
 H27C), C29(H29A,H29B,H29C), C30(H30A,H30B,H30C), C32(H32A,H32B,H32C), C33(H33A,
 H33B,H33C)
;
_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
Zn1 Zn 0.25235(3) 0.73439(3) 0.40331(2) 0.01477(10) Uani 1 1 d . . . . .
Cl1 Cl 0.16365(5) 0.78572(6) 0.46988(3) 0.02251(15) Uani 1 1 d . . . . .
Cl2 Cl 0.30390(6) 0.55383(6) 0.40117(3) 0.02510(16) Uani 1 1 d . . . . .
O1 O 0.42780(17) 0.64398(18) 0.57674(9) 0.0254(4) Uani 1 1 d . . . . .
O2 O -0.02323(18) 0.5245(2) 0.38295(10) 0.0331(5) Uani 1 1 d . . . . .
N1 N 0.28132(18) 0.85441(18) 0.34134(10) 0.0152(4) Uani 1 1 d . . . . .
N2 N 0.40239(18) 0.80866(19) 0.44642(10) 0.0173(5) Uani 1 1 d . . . . .
N3 N 0.47999(18) 0.7904(2) 0.49606(10) 0.0171(5) Uani 1 1 d . . . . .
H3 H 0.466(3) 0.745(3) 0.5248(16) 0.020 Uiso 1 1 d . U . . .
N4 N 0.9373(2) 0.8168(2) 0.68674(11) 0.0279(6) Uani 1 1 d . . . . .
N5 N 0.11505(17) 0.73035(19) 0.32444(9) 0.0151(4) Uani 1 1 d . . . . .
N6 N 0.03022(17) 0.66438(19) 0.30391(10) 0.0157(4) Uani 1 1 d . . . . .
H6 H 0.010(3) 0.616(3) 0.3306(15) 0.019 Uiso 1 1 d . U . . .
N7 N -0.3522(2) 0.4158(2) 0.11353(12) 0.0313(6) Uani 1 1 d . . . . .
N8 N 0.3796(2) 0.4739(2) 0.60481(12) 0.0293(6) Uani 1 1 d . . . . .
N9 N 0.0541(2) 0.3918(2) 0.45019(12) 0.0333(6) Uani 1 1 d . . . . .
C1 C 0.2087(2) 0.8745(2) 0.28982(11) 0.0159(5) Uani 1 1 d . . . . .
C2 C 0.2206(2) 0.9604(2) 0.25148(12) 0.0189(6) Uani 1 1 d . . . . .
H2 H 0.169450 0.972843 0.214777 0.023 Uiso 1 1 calc R U . . .
C3 C 0.3089(2) 1.0271(2) 0.26813(13) 0.0213(6) Uani 1 1 d . . . . .
H3A H 0.318263 1.087276 0.243052 0.026 Uiso 1 1 calc R U . . .
C4 C 0.3842(2) 1.0064(2) 0.32168(13) 0.0205(6) Uani 1 1 d . . . . .
H4 H 0.445278 1.051653 0.333397 0.025 Uiso 1 1 calc R U . . .
C5 C 0.3680(2) 0.9184(2) 0.35744(12) 0.0167(5) Uani 1 1 d . . . . .
C6 C 0.4393(2) 0.8857(2) 0.41499(12) 0.0164(5) Uani 1 1 d . . . . .
C7 C 0.5416(2) 0.9174(2) 0.44520(12) 0.0174(5) Uani 1 1 d . . . . .
H7 H 0.584949 0.970596 0.432657 0.021 Uiso 1 1 calc R U . . .
C8 C 0.5658(2) 0.8539(2) 0.49750(12) 0.0163(5) Uani 1 1 d . . . . .
C9 C 0.6609(2) 0.8453(2) 0.54668(12) 0.0177(5) Uani 1 1 d . . . . .
C10 C 0.7374(2) 0.9294(2) 0.55677(12) 0.0181(5) Uani 1 1 d . . . . .
H10 H 0.726989 0.993393 0.531354 0.022 Uiso 1 1 calc R U . . .
C11 C 0.8277(2) 0.9216(2) 0.60276(13) 0.0200(6) Uani 1 1 d . . . . .
H11 H 0.877923 0.980316 0.608455 0.024 Uiso 1 1 calc R U . . .
C12 C 0.8467(2) 0.8275(2) 0.64160(12) 0.0205(6) Uani 1 1 d . . . . .
C13 C 0.7690(2) 0.7435(3) 0.63129(13) 0.0223(6) Uani 1 1 d . . . . .
H13 H 0.778493 0.679377 0.656608 0.027 Uiso 1 1 calc R U . . .
C14 C 0.6796(2) 0.7528(2) 0.58524(13) 0.0220(6) Uani 1 1 d . . . . .
H14 H 0.628884 0.694436 0.579442 0.026 Uiso 1 1 calc R U . . .
C15 C 1.0153(3) 0.9038(3) 0.69751(15) 0.0334(7) Uani 1 1 d . . . . .
H15A H 1.035005 0.919833 0.660437 0.050 Uiso 1 1 calc R U . . .
H15B H 1.077113 0.878742 0.728283 0.050 Uiso 1 1 calc R U . . .
H15C H 0.987109 0.972007 0.711143 0.050 Uiso 1 1 calc R U . . .
C16 C 0.9522(3) 0.7206(3) 0.72602(15) 0.0352(8) Uani 1 1 d . . . . .
H16A H 0.899802 0.721706 0.748987 0.053 Uiso 1 1 calc R U . . .
H16B H 1.022380 0.723363 0.753510 0.053 Uiso 1 1 calc R U . . .
H16C H 0.944578 0.651484 0.702241 0.053 Uiso 1 1 calc R U . . .
C17 C 0.1190(2) 0.7971(2) 0.27901(11) 0.0153(5) Uani 1 1 d . . . . .
C18 C 0.0360(2) 0.7753(2) 0.22848(12) 0.0163(5) Uani 1 1 d . . . . .
H18 H 0.021223 0.811747 0.190706 0.020 Uiso 1 1 calc R U . . .
C19 C -0.0201(2) 0.6881(2) 0.24608(11) 0.0156(5) Uani 1 1 d . . . . .
C20 C -0.1097(2) 0.6220(2) 0.21325(12) 0.0171(5) Uani 1 1 d . . . . .
C21 C -0.1586(2) 0.6447(2) 0.15307(12) 0.0180(5) Uani 1 1 d . . . . .
H21 H -0.136096 0.707462 0.134335 0.022 Uiso 1 1 calc R U . . .
C22 C -0.2386(2) 0.5782(2) 0.12036(12) 0.0206(6) Uani 1 1 d . . . . .
H22 H -0.270654 0.596664 0.079802 0.025 Uiso 1 1 calc R U . . .
C23 C -0.2735(2) 0.4833(3) 0.14602(12) 0.0211(6) Uani 1 1 d . . . . .
C24 C -0.2240(3) 0.4601(3) 0.20648(13) 0.0268(7) Uani 1 1 d . . . . .
H24 H -0.245414 0.396524 0.225113 0.032 Uiso 1 1 calc R U . . .
C25 C -0.1448(2) 0.5283(3) 0.23919(13) 0.0241(6) Uani 1 1 d . . . . .
H25 H -0.113535 0.511326 0.280036 0.029 Uiso 1 1 calc R U . . .
C26 C -0.4073(3) 0.4460(3) 0.05403(14) 0.0343(8) Uani 1 1 d . . . . .
H26A H -0.433302 0.523174 0.053684 0.051 Uiso 1 1 calc R U . . .
H26B H -0.466313 0.394572 0.039561 0.051 Uiso 1 1 calc R U . . .
H26C H -0.359993 0.440916 0.027946 0.051 Uiso 1 1 calc R U . . .
C27 C -0.3902(3) 0.3222(3) 0.14205(14) 0.0283(7) Uani 1 1 d . . . . .
H27A H -0.334327 0.266491 0.155012 0.042 Uiso 1 1 calc R U . . .
H27B H -0.450020 0.287417 0.113567 0.042 Uiso 1 1 calc R U . . .
H27C H -0.411906 0.349522 0.176838 0.042 Uiso 1 1 calc R U . . .
C28 C 0.4318(2) 0.5405(3) 0.57690(13) 0.0248(6) Uani 1 1 d . . . . .
H28 H 0.475473 0.505873 0.555456 0.030 Uiso 1 1 calc R U . . .
C29 C 0.3102(3) 0.5210(3) 0.63780(18) 0.0395(9) Uani 1 1 d . . . . .
H29A H 0.347282 0.526263 0.680287 0.059 Uiso 1 1 calc R U . . .
H29B H 0.248881 0.472314 0.633016 0.059 Uiso 1 1 calc R U . . .
H29C H 0.287659 0.596179 0.622337 0.059 Uiso 1 1 calc R U . . .
C30 C 0.3972(4) 0.3530(3) 0.60850(18) 0.0440(9) Uani 1 1 d . . . . .
H30A H 0.442382 0.331726 0.582921 0.066 Uiso 1 1 calc R U . . .
H30B H 0.330086 0.313788 0.595099 0.066 Uiso 1 1 calc R U . . .
H30C H 0.431057 0.332099 0.649986 0.066 Uiso 1 1 calc R U . . .
C31 C 0.0487(3) 0.4928(3) 0.42526(14) 0.0290(7) Uani 1 1 d . . . . .
H31 H 0.103969 0.544153 0.441048 0.035 Uiso 1 1 calc R U . . .
C32 C -0.0262(4) 0.3088(3) 0.4271(2) 0.0461(10) Uani 1 1 d . . . . .
H32A H -0.069615 0.299704 0.455056 0.069 Uiso 1 1 calc R U . . .
H32B H 0.006567 0.236789 0.422243 0.069 Uiso 1 1 calc R U . . .
H32C H -0.069924 0.333859 0.388219 0.069 Uiso 1 1 calc R U . . .
C33 C 0.1411(4) 0.3607(4) 0.49974(18) 0.0521(11) Uani 1 1 d . . . . .
H33A H 0.178668 0.297413 0.488012 0.078 Uiso 1 1 calc R U . . .
H33B H 0.114947 0.338811 0.533937 0.078 Uiso 1 1 calc R U . . .
H33C H 0.188590 0.424952 0.510888 0.078 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
Zn1 Cl1 2.2558(7) . ?
Zn1 Cl2 2.2574(7) . ?
Zn1 N1 2.130(2) . ?
Zn1 N2 2.165(2) . ?
Zn1 N5 2.215(2) . ?
O1 C28 1.231(4) . ?
O2 C31 1.233(4) . ?
N1 C1 1.343(3) . ?
N1 C5 1.346(4) . ?
N2 N3 1.344(3) . ?
N2 C6 1.340(4) . ?
N3 H3 0.91(4) . ?
N3 C8 1.358(4) . ?
N4 C12 1.375(4) . ?
N4 C15 1.437(4) . ?
N4 C16 1.442(4) . ?
N5 N6 1.351(3) . ?
N5 C17 1.330(3) . ?
N6 H6 0.93(4) . ?
N6 C19 1.360(3) . ?
N7 C23 1.373(4) . ?
N7 C26 1.426(4) . ?
N7 C27 1.450(4) . ?
N8 C28 1.327(4) . ?
N8 C29 1.455(4) . ?
N8 C30 1.454(4) . ?
N9 C31 1.326(4) . ?
N9 C32 1.447(5) . ?
N9 C33 1.445(5) . ?
C1 C2 1.389(4) . ?
C1 C17 1.472(4) . ?
C2 H2 0.9500 . ?
C2 C3 1.382(4) . ?
C3 H3A 0.9500 . ?
C3 C4 1.395(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.386(4) . ?
C5 C6 1.470(4) . ?
C6 C7 1.404(4) . ?
C7 H7 0.9500 . ?
C7 C8 1.392(4) . ?
C8 C9 1.463(4) . ?
C9 C10 1.399(4) . ?
C9 C14 1.398(4) . ?
C10 H10 0.9500 . ?
C10 C11 1.380(4) . ?
C11 H11 0.9500 . ?
C11 C12 1.417(4) . ?
C12 C13 1.409(4) . ?
C13 H13 0.9500 . ?
C13 C14 1.375(4) . ?
C14 H14 0.9500 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 C18 1.404(4) . ?
C18 H18 0.9500 . ?
C18 C19 1.397(4) . ?
C19 C20 1.460(4) . ?
C20 C21 1.401(4) . ?
C20 C25 1.401(4) . ?
C21 H21 0.9500 . ?
C21 C22 1.378(4) . ?
C22 H22 0.9500 . ?
C22 C23 1.409(4) . ?
C23 C24 1.409(4) . ?
C24 H24 0.9500 . ?
C24 C25 1.385(4) . ?
C25 H25 0.9500 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C28 H28 0.9500 . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?
C31 H31 0.9500 . ?
C32 H32A 0.9800 . ?
C32 H32B 0.9800 . ?
C32 H32C 0.9800 . ?
C33 H33A 0.9800 . ?
C33 H33B 0.9800 . ?
C33 H33C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
Cl1 Zn1 Cl2 119.17(3) . . ?
N1 Zn1 Cl1 119.91(6) . . ?
N1 Zn1 Cl2 120.87(6) . . ?
N1 Zn1 N2 74.42(8) . . ?
N1 Zn1 N5 73.30(8) . . ?
N2 Zn1 Cl1 98.89(6) . . ?
N2 Zn1 Cl2 98.71(7) . . ?
N2 Zn1 N5 147.71(8) . . ?
N5 Zn1 Cl1 96.17(6) . . ?
N5 Zn1 Cl2 98.57(6) . . ?
C1 N1 Zn1 120.30(18) . . ?
C1 N1 C5 120.4(2) . . ?
C5 N1 Zn1 118.93(17) . . ?
N3 N2 Zn1 137.11(18) . . ?
C6 N2 Zn1 116.74(17) . . ?
C6 N2 N3 105.6(2) . . ?
N2 N3 H3 118(2) . . ?
N2 N3 C8 112.3(2) . . ?
C8 N3 H3 130(2) . . ?
C12 N4 C15 120.7(3) . . ?
C12 N4 C16 120.1(3) . . ?
C15 N4 C16 119.2(3) . . ?
N6 N5 Zn1 136.93(17) . . ?
C17 N5 Zn1 116.46(17) . . ?
C17 N5 N6 105.7(2) . . ?
N5 N6 H6 119(2) . . ?
N5 N6 C19 111.9(2) . . ?
C19 N6 H6 129(2) . . ?
C23 N7 C26 120.3(3) . . ?
C23 N7 C27 120.2(2) . . ?
C26 N7 C27 118.9(3) . . ?
C28 N8 C29 120.6(3) . . ?
C28 N8 C30 121.5(3) . . ?
C30 N8 C29 117.6(3) . . ?
C31 N9 C32 120.4(3) . . ?
C31 N9 C33 121.2(3) . . ?
C33 N9 C32 118.4(3) . . ?
N1 C1 C2 121.6(2) . . ?
N1 C1 C17 113.5(2) . . ?
C2 C1 C17 125.0(2) . . ?
C1 C2 H2 120.9 . . ?
C3 C2 C1 118.3(3) . . ?
C3 C2 H2 120.9 . . ?
C2 C3 H3A 119.9 . . ?
C2 C3 C4 120.1(3) . . ?
C4 C3 H3A 119.9 . . ?
C3 C4 H4 120.7 . . ?
C5 C4 C3 118.5(3) . . ?
C5 C4 H4 120.7 . . ?
N1 C5 C4 121.1(2) . . ?
N1 C5 C6 113.6(2) . . ?
C4 C5 C6 125.3(2) . . ?
N2 C6 C5 115.8(2) . . ?
N2 C6 C7 110.8(2) . . ?
C7 C6 C5 133.5(3) . . ?
C6 C7 H7 127.5 . . ?
C8 C7 C6 105.1(2) . . ?
C8 C7 H7 127.5 . . ?
N3 C8 C7 106.3(2) . . ?
N3 C8 C9 121.6(2) . . ?
C7 C8 C9 132.1(3) . . ?
C10 C9 C8 121.2(2) . . ?
C14 C9 C8 121.6(3) . . ?
C14 C9 C10 117.2(3) . . ?
C9 C10 H10 119.2 . . ?
C11 C10 C9 121.6(3) . . ?
C11 C10 H10 119.2 . . ?
C10 C11 H11 119.4 . . ?
C10 C11 C12 121.1(3) . . ?
C12 C11 H11 119.4 . . ?
N4 C12 C11 122.0(3) . . ?
N4 C12 C13 121.1(3) . . ?
C13 C12 C11 116.9(3) . . ?
C12 C13 H13 119.4 . . ?
C14 C13 C12 121.2(3) . . ?
C14 C13 H13 119.4 . . ?
C9 C14 H14 119.0 . . ?
C13 C14 C9 122.1(3) . . ?
C13 C14 H14 119.0 . . ?
N4 C15 H15A 109.5 . . ?
N4 C15 H15B 109.5 . . ?
N4 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N4 C16 H16A 109.5 . . ?
N4 C16 H16B 109.5 . . ?
N4 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N5 C17 C1 115.9(2) . . ?
N5 C17 C18 111.4(2) . . ?
C18 C17 C1 132.7(2) . . ?
C17 C18 H18 127.7 . . ?
C19 C18 C17 104.7(2) . . ?
C19 C18 H18 127.7 . . ?
N6 C19 C18 106.3(2) . . ?
N6 C19 C20 121.5(2) . . ?
C18 C19 C20 132.0(2) . . ?
C21 C20 C19 121.0(2) . . ?
C21 C20 C25 117.5(2) . . ?
C25 C20 C19 121.4(2) . . ?
C20 C21 H21 119.2 . . ?
C22 C21 C20 121.6(3) . . ?
C22 C21 H21 119.2 . . ?
C21 C22 H22 119.4 . . ?
C21 C22 C23 121.2(3) . . ?
C23 C22 H22 119.4 . . ?
N7 C23 C22 121.6(3) . . ?
N7 C23 C24 121.2(3) . . ?
C22 C23 C24 117.2(3) . . ?
C23 C24 H24 119.4 . . ?
C25 C24 C23 121.1(3) . . ?
C25 C24 H24 119.4 . . ?
C20 C25 H25 119.3 . . ?
C24 C25 C20 121.3(3) . . ?
C24 C25 H25 119.3 . . ?
N7 C26 H26A 109.5 . . ?
N7 C26 H26B 109.5 . . ?
N7 C26 H26C 109.5 . . ?
H26A C26 H26B 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
N7 C27 H27A 109.5 . . ?
N7 C27 H27B 109.5 . . ?
N7 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
O1 C28 N8 124.8(3) . . ?
O1 C28 H28 117.6 . . ?
N8 C28 H28 117.6 . . ?
N8 C29 H29A 109.5 . . ?
N8 C29 H29B 109.5 . . ?
N8 C29 H29C 109.5 . . ?
H29A C29 H29B 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
N8 C30 H30A 109.5 . . ?
N8 C30 H30B 109.5 . . ?
N8 C30 H30C 109.5 . . ?
H30A C30 H30B 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
O2 C31 N9 124.4(3) . . ?
O2 C31 H31 117.8 . . ?
N9 C31 H31 117.8 . . ?
N9 C32 H32A 109.5 . . ?
N9 C32 H32B 109.5 . . ?
N9 C32 H32C 109.5 . . ?
H32A C32 H32B 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
N9 C33 H33A 109.5 . . ?
N9 C33 H33B 109.5 . . ?
N9 C33 H33C 109.5 . . ?
H33A C33 H33B 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N3 H3 O1 0.91(4) 1.86(4) 2.773(3) 174(3) . yes
N6 H6 O2 0.93(4) 1.77(4) 2.703(3) 178(3) . yes

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
Zn1 N1 C1 C2 173.1(2) . . . . ?
Zn1 N1 C1 C17 -7.3(3) . . . . ?
Zn1 N1 C5 C4 -172.4(2) . . . . ?
Zn1 N1 C5 C6 7.2(3) . . . . ?
Zn1 N2 N3 C8 170.9(2) . . . . ?
Zn1 N2 C6 C5 6.0(3) . . . . ?
Zn1 N2 C6 C7 -173.29(18) . . . . ?
Zn1 N5 N6 C19 -167.82(19) . . . . ?
Zn1 N5 C17 C1 -6.7(3) . . . . ?
Zn1 N5 C17 C18 171.01(17) . . . . ?
N1 C1 C2 C3 -1.3(4) . . . . ?
N1 C1 C17 N5 9.1(3) . . . . ?
N1 C1 C17 C18 -168.1(3) . . . . ?
N1 C5 C6 N2 -8.5(3) . . . . ?
N1 C5 C6 C7 170.6(3) . . . . ?
N2 N3 C8 C7 0.1(3) . . . . ?
N2 N3 C8 C9 -178.2(2) . . . . ?
N2 C6 C7 C8 0.3(3) . . . . ?
N3 N2 C6 C5 179.0(2) . . . . ?
N3 N2 C6 C7 -0.3(3) . . . . ?
N3 C8 C9 C10 -162.6(3) . . . . ?
N3 C8 C9 C14 17.9(4) . . . . ?
N4 C12 C13 C14 -178.3(3) . . . . ?
N5 N6 C19 C18 -0.2(3) . . . . ?
N5 N6 C19 C20 175.7(2) . . . . ?
N5 C17 C18 C19 -0.5(3) . . . . ?
N6 N5 C17 C1 -177.4(2) . . . . ?
N6 N5 C17 C18 0.3(3) . . . . ?
N6 C19 C20 C21 -177.7(3) . . . . ?
N6 C19 C20 C25 -2.8(4) . . . . ?
N7 C23 C24 C25 -180.0(3) . . . . ?
C1 N1 C5 C4 0.3(4) . . . . ?
C1 N1 C5 C6 179.8(2) . . . . ?
C1 C2 C3 C4 1.1(4) . . . . ?
C1 C17 C18 C19 176.8(3) . . . . ?
C2 C1 C17 N5 -171.4(3) . . . . ?
C2 C1 C17 C18 11.5(5) . . . . ?
C2 C3 C4 C5 -0.3(4) . . . . ?
C3 C4 C5 N1 -0.4(4) . . . . ?
C3 C4 C5 C6 -179.9(3) . . . . ?
C4 C5 C6 N2 171.0(3) . . . . ?
C4 C5 C6 C7 -9.9(5) . . . . ?
C5 N1 C1 C2 0.5(4) . . . . ?
C5 N1 C1 C17 -179.9(2) . . . . ?
C5 C6 C7 C8 -178.8(3) . . . . ?
C6 N2 N3 C8 0.1(3) . . . . ?
C6 C7 C8 N3 -0.2(3) . . . . ?
C6 C7 C8 C9 177.8(3) . . . . ?
C7 C8 C9 C10 19.6(5) . . . . ?
C7 C8 C9 C14 -159.9(3) . . . . ?
C8 C9 C10 C11 -179.5(3) . . . . ?
C8 C9 C14 C13 179.5(3) . . . . ?
C9 C10 C11 C12 0.3(4) . . . . ?
C10 C9 C14 C13 0.0(4) . . . . ?
C10 C11 C12 N4 178.4(3) . . . . ?
C10 C11 C12 C13 -0.6(4) . . . . ?
C11 C12 C13 C14 0.6(4) . . . . ?
C12 C13 C14 C9 -0.3(5) . . . . ?
C14 C9 C10 C11 0.1(4) . . . . ?
C15 N4 C12 C11 2.2(5) . . . . ?
C15 N4 C12 C13 -179.0(3) . . . . ?
C16 N4 C12 C11 178.6(3) . . . . ?
C16 N4 C12 C13 -2.5(5) . . . . ?
C17 N5 N6 C19 -0.1(3) . . . . ?
C17 C1 C2 C3 179.2(3) . . . . ?
C17 C18 C19 N6 0.4(3) . . . . ?
C17 C18 C19 C20 -174.9(3) . . . . ?
C18 C19 C20 C21 -3.0(5) . . . . ?
C18 C19 C20 C25 171.9(3) . . . . ?
C19 C20 C21 C22 175.4(3) . . . . ?
C19 C20 C25 C24 -174.5(3) . . . . ?
C20 C21 C22 C23 -0.9(4) . . . . ?
C21 C20 C25 C24 0.6(5) . . . . ?
C21 C22 C23 N7 -179.1(3) . . . . ?
C21 C22 C23 C24 0.6(4) . . . . ?
C22 C23 C24 C25 0.4(5) . . . . ?
C23 C24 C25 C20 -1.0(5) . . . . ?
C25 C20 C21 C22 0.3(4) . . . . ?
C26 N7 C23 C22 -5.7(5) . . . . ?
C26 N7 C23 C24 174.7(3) . . . . ?
C27 N7 C23 C22 -176.7(3) . . . . ?
C27 N7 C23 C24 3.6(5) . . . . ?
C29 N8 C28 O1 0.9(5) . . . . ?
C30 N8 C28 O1 -173.1(3) . . . . ?
C32 N9 C31 O2 1.7(5) . . . . ?
C33 N9 C31 O2 -180.0(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
