# Supplementary Information (SI) for Organic & Biomolecular Chemistry.
# 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_AT019_MD1
_database_code_depnum_ccdc_archive 'CCDC 2442944'
loop_
_audit_author_name
_audit_author_address
'Katherine Robertson'
;Saint Marys University
Canada
;
_audit_update_record             
;
2025-04-10 deposited with the CCDC.	2025-07-29 downloaded from the CCDC.
;

#============================================================================== 

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '0.5((C46 H40 N4)4), 2(H2 O)'
_chemical_formula_sum            'C92 H84 N8 O2'
_chemical_formula_weight         1333.67

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   12.1766(7)
_cell_length_b                   15.8845(8)
_cell_length_c                   21.0428(12)
_cell_angle_alpha                78.814(2)
_cell_angle_beta                 77.092(2)
_cell_angle_gamma                67.6536(19)
_cell_volume                     3642.3(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9789
_cell_measurement_theta_min      2.2287
_cell_measurement_theta_max      26.3547

_exptl_crystal_description       'long rod'
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.216
_exptl_crystal_F_000             1416
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.577
_exptl_crystal_size_mid          0.034
_exptl_crystal_size_min          0.026
_exptl_absorpt_coefficient_mu    0.073
_shelx_estimated_absorpt_T_min   0.959
_shelx_estimated_absorpt_T_max   0.998
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6686
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   
;
Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015).
J. Appl. Cryst. 48, 3-10.
;
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_source_type              'Incoatec I\mS 3.0'
_diffrn_source_source            'microfocus sealed tube'
_diffrn_source_power             0.07
_diffrn_source_current           1.4
_diffrn_source_voltage           50
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_measurement_device       'κ--geometry diffractometer'
_diffrn_detector_type            'Bruker PHOTON III'
_diffrn_detector                 '100 \\times 140 mm^2^ CMOS sensor'
_diffrn_detector_area_resol_mean 7.3910
_diffrn_reflns_number            192295
_diffrn_reflns_av_unetI/netI     0.0390
_diffrn_reflns_av_R_equivalents  0.0927
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         1.813
_diffrn_reflns_theta_max         26.401
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             14904
_reflns_number_gt                9237
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker Instrument Service v8.5.0.11 RC8'
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1049P)²+2.6000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     'dual space'
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     'SHELXL-2019/2 (Sheldrick 2019)'
_refine_ls_extinction_coef       0.0046(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         14904
_refine_ls_number_parameters     956
_refine_ls_number_restraints     836
_refine_ls_R_factor_all          0.1307
_refine_ls_R_factor_gt           0.0689
_refine_ls_wR_factor_ref         0.2400
_refine_ls_wR_factor_gt          0.1704
_refine_ls_goodness_of_fit_ref   1.164
_refine_ls_restrained_S_all      1.132
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O -0.2534(2) 0.75037(17) 0.48842(12) 0.0481(6) Uani 1 1 d D . . . .
H1O H -0.327(2) 0.756(3) 0.503(2) 0.072 Uiso 1 1 d D U . . .
H2O H -0.215(3) 0.740(3) 0.5209(15) 0.072 Uiso 1 1 d D U . . .
O2 O 0.7585(2) 0.25520(17) 0.00613(11) 0.0490(6) Uani 1 1 d D . . . .
H3O H 0.728(4) 0.275(3) -0.0287(14) 0.073 Uiso 1 1 d D U . . .
H4O H 0.734(4) 0.211(2) 0.022(2) 0.073 Uiso 1 1 d D U . . .
N1 N -0.1434(2) 0.57186(15) 0.42000(12) 0.0336(5) Uani 1 1 d D . . . .
H1N H -0.166(3) 0.6213(17) 0.4412(15) 0.050 Uiso 1 1 d D U . . .
N2 N 0.0080(2) 0.46534(15) 0.48555(11) 0.0339(5) Uani 1 1 d . . . . .
N3 N -0.2897(2) 0.96708(16) 0.44257(12) 0.0351(5) Uani 1 1 d D . . . .
H3N H -0.289(3) 0.9086(14) 0.4544(17) 0.053 Uiso 1 1 d D U . . .
N4 N -0.4986(2) 1.04132(15) 0.49261(12) 0.0346(5) Uani 1 1 d . . . . .
N5 N 0.6250(2) 0.42208(16) 0.08870(12) 0.0355(5) Uani 1 1 d D . . . .
H5N H 0.659(3) 0.3784(19) 0.0615(15) 0.053 Uiso 1 1 d D U . . .
N6 N 0.4751(2) 0.52778(16) 0.02195(11) 0.0358(5) Uani 1 1 d . . . . .
N7 N 1.0310(2) 0.14534(16) -0.05288(12) 0.0371(6) Uani 1 1 d D . . . .
H7N H 0.9555(19) 0.171(2) -0.0320(16) 0.056 Uiso 1 1 d D U . . .
N8 N 1.0523(2) -0.01536(16) -0.01808(12) 0.0369(5) Uani 1 1 d . . . . .
C1 C -0.0622(3) 0.48632(18) 0.43812(14) 0.0336(6) Uani 1 1 d . . . . .
C2 C -0.0623(3) 0.42535(19) 0.39844(14) 0.0355(6) Uani 1 1 d . . . . .
C3 C -0.1454(3) 0.47603(19) 0.35624(15) 0.0364(6) Uani 1 1 d . . . . .
H3 H -0.164969 0.452384 0.323837 0.044 Uiso 1 1 calc R U . . .
C4 C -0.1944(3) 0.56634(19) 0.36958(14) 0.0334(6) Uani 1 1 d . . . . .
C5 C 0.0203(3) 0.32828(19) 0.39844(14) 0.0352(6) Uani 1 1 d . . . . .
C6 C -0.0156(3) 0.25739(19) 0.43557(14) 0.0371(6) Uani 1 1 d . . . . .
C7 C 0.0663(3) 0.1674(2) 0.43499(15) 0.0414(7) Uani 1 1 d . . . . .
H7 H 0.042484 0.119002 0.460492 0.050 Uiso 1 1 calc R U . . .
C8 C 0.1811(3) 0.1463(2) 0.39847(16) 0.0419(7) Uani 1 1 d . . . . .
C9 C 0.2138(3) 0.2182(2) 0.36123(17) 0.0444(7) Uani 1 1 d . . . . .
H9 H 0.291790 0.205102 0.335518 0.053 Uiso 1 1 calc R U . . .
C10 C 0.1349(3) 0.3090(2) 0.36061(16) 0.0411(7) Uani 1 1 d . . . . .
C11 C -0.1394(3) 0.2762(2) 0.47585(18) 0.0507(8) Uani 1 1 d . . . . .
H11A H -0.148030 0.218200 0.497844 0.076 Uiso 1 1 calc R U . . .
H11B H -0.200007 0.306711 0.447080 0.076 Uiso 1 1 calc R U . . .
H11C H -0.150694 0.315897 0.508862 0.076 Uiso 1 1 calc R U . . .
C12 C 0.2677(3) 0.0489(2) 0.39747(18) 0.0532(9) Uani 1 1 d . . . . .
H12A H 0.236266 0.008949 0.432084 0.080 Uiso 1 1 calc R U . . .
H12B H 0.345975 0.045292 0.405034 0.080 Uiso 1 1 calc R U . . .
H12C H 0.277067 0.029116 0.354654 0.080 Uiso 1 1 calc R U . . .
C13 C 0.1743(4) 0.3836(2) 0.3189(2) 0.0639(11) Uani 1 1 d . . . . .
H13A H 0.122039 0.414171 0.285764 0.096 Uiso 1 1 calc R U . . .
H13B H 0.257713 0.357146 0.297105 0.096 Uiso 1 1 calc R U . . .
H13C H 0.169058 0.428420 0.346679 0.096 Uiso 1 1 calc R U . . .
C14 C -0.2759(2) 0.64609(18) 0.33521(14) 0.0329(6) Uani 1 1 d . . . . .
C15 C -0.3482(3) 0.6337(2) 0.29653(14) 0.0352(6) Uani 1 1 d . . . . .
H15 H -0.346088 0.573604 0.295189 0.042 Uiso 1 1 calc R U . . .
C16 C -0.4215(3) 0.7067(2) 0.26088(15) 0.0373(6) Uani 1 1 d . . . . .
H16 H -0.468563 0.696395 0.234767 0.045 Uiso 1 1 calc R U . . .
C17 C -0.4281(3) 0.7973(2) 0.26245(14) 0.0358(6) Uani 1 1 d . . . . .
C18 C -0.5029(3) 0.8750(2) 0.22663(16) 0.0440(7) Uani 1 1 d . . . . .
H18 H -0.551350 0.866874 0.200340 0.053 Uiso 1 1 calc R U . . .
C19 C -0.5065(3) 0.9612(2) 0.22921(17) 0.0479(8) Uani 1 1 d . . . . .
H19 H -0.556527 1.012279 0.204509 0.057 Uiso 1 1 calc R U . . .
C20 C -0.4363(3) 0.9744(2) 0.26833(16) 0.0475(8) Uani 1 1 d . . . . .
H20 H -0.439627 1.034586 0.270231 0.057 Uiso 1 1 calc R U . . .
C21 C -0.3631(3) 0.9013(2) 0.30377(16) 0.0427(7) Uani 1 1 d . . . . .
H21 H -0.315761 0.911082 0.329940 0.051 Uiso 1 1 calc R U . . .
C22 C -0.3574(3) 0.81096(19) 0.30168(14) 0.0356(6) Uani 1 1 d . . . . .
C23 C -0.2818(3) 0.73410(19) 0.33717(14) 0.0362(6) Uani 1 1 d . . . . .
H23 H -0.233580 0.743231 0.363128 0.043 Uiso 1 1 calc R U . . .
C24 C -0.3886(2) 1.04367(19) 0.45957(14) 0.0339(6) Uani 1 1 d . . . . .
C25 C -0.3564(3) 1.12092(19) 0.43880(15) 0.0368(6) Uani 1 1 d . . . . .
C26 C -0.2352(3) 1.08958(19) 0.40851(15) 0.0381(7) Uani 1 1 d . . . . .
H26 H -0.188570 1.127082 0.389220 0.046 Uiso 1 1 calc R U . . .
C27 C -0.1948(3) 0.99453(19) 0.41145(15) 0.0363(6) Uani 1 1 d . . . . .
C28 C -0.4337(2) 1.21748(19) 0.44750(15) 0.0346(6) Uani 1 1 d . . . . .
C29 C -0.4822(3) 1.2783(2) 0.39451(15) 0.0403(7) Uani 1 1 d . . . . .
C30 C -0.5481(3) 1.3697(2) 0.40267(16) 0.0436(7) Uani 1 1 d . . . . .
H30 H -0.579667 1.410767 0.366415 0.052 Uiso 1 1 calc R U . . .
C31 C -0.5691(3) 1.4027(2) 0.46240(16) 0.0418(7) Uani 1 1 d . . . . .
C32 C -0.5214(3) 1.34177(19) 0.51416(15) 0.0390(7) Uani 1 1 d . . . . .
H32 H -0.535102 1.363441 0.555279 0.047 Uiso 1 1 calc R U . . .
C33 C -0.4539(3) 1.24967(19) 0.50830(15) 0.0367(6) Uani 1 1 d . . . . .
C34 C -0.4612(3) 1.2450(2) 0.32911(17) 0.0525(8) Uani 1 1 d . . . . .
H34A H -0.504634 1.295126 0.298557 0.079 Uiso 1 1 calc R U . . .
H34B H -0.490317 1.193974 0.334626 0.079 Uiso 1 1 calc R U . . .
H34C H -0.374842 1.224192 0.311524 0.079 Uiso 1 1 calc R U . . .
C35 C -0.6408(3) 1.5024(2) 0.47096(18) 0.0517(8) Uani 1 1 d . . . . .
H35A H -0.642108 1.512956 0.515520 0.078 Uiso 1 1 calc R U . . .
H35B H -0.723335 1.517304 0.463915 0.078 Uiso 1 1 calc R U . . .
H35C H -0.603306 1.541336 0.438976 0.078 Uiso 1 1 calc R U . . .
C36 C -0.4035(3) 1.1874(2) 0.56637(16) 0.0449(7) Uani 1 1 d . . . . .
H36A H -0.439139 1.139422 0.579243 0.067 Uiso 1 1 calc R U . . .
H36B H -0.422579 1.222969 0.603100 0.067 Uiso 1 1 calc R U . . .
H36C H -0.315982 1.159095 0.554682 0.067 Uiso 1 1 calc R U . . .
C37 C -0.0776(3) 0.93042(19) 0.38659(14) 0.0357(6) Uani 1 1 d . . . . .
C38 C 0.0196(3) 0.9628(2) 0.36160(16) 0.0438(7) Uani 1 1 d . . . . .
H38 H 0.006964 1.025666 0.361194 0.053 Uiso 1 1 calc R U . . .
C39 C 0.1309(3) 0.9045(2) 0.33819(16) 0.0434(7) Uani 1 1 d . . . . .
H39 H 0.194305 0.927728 0.321441 0.052 Uiso 1 1 calc R U . . .
C40 C 0.1539(3) 0.8104(2) 0.33828(14) 0.0362(6) Uani 1 1 d . . . . .
C41 C 0.2686(3) 0.7480(2) 0.31550(15) 0.0407(7) Uani 1 1 d . . . . .
H41 H 0.333519 0.769635 0.298757 0.049 Uiso 1 1 calc R U . . .
C42 C 0.2878(3) 0.6575(2) 0.31710(16) 0.0450(7) Uani 1 1 d . . . . .
H42 H 0.365924 0.616204 0.302422 0.054 Uiso 1 1 calc R U . . .
C43 C 0.1919(3) 0.6254(2) 0.34048(18) 0.0489(8) Uani 1 1 d . . . . .
H43 H 0.205221 0.562352 0.340819 0.059 Uiso 1 1 calc R U . . .
C44 C 0.0800(3) 0.6833(2) 0.36270(18) 0.0477(8) Uani 1 1 d . . . . .
H44 H 0.016279 0.660151 0.378473 0.057 Uiso 1 1 calc R U . . .
C45 C 0.0573(3) 0.7774(2) 0.36265(15) 0.0374(6) Uani 1 1 d . . . . .
C46 C -0.0571(3) 0.8391(2) 0.38693(15) 0.0384(7) Uani 1 1 d . . . . .
H46 H -0.121429 0.816860 0.403905 0.046 Uiso 1 1 calc R U . . .
C47 C 0.5273(3) 0.50010(19) 0.07741(14) 0.0368(6) Uani 1 1 d . . . . .
C48 C 0.4898(3) 0.5479(2) 0.13167(15) 0.0392(7) Uani 1 1 d . . . . .
C49 C 0.5671(3) 0.4965(2) 0.17684(15) 0.0416(7) Uani 1 1 d . . . . .
H49 H 0.562635 0.511843 0.219020 0.050 Uiso 1 1 calc R U . . .
C50 C 0.6513(3) 0.4193(2) 0.14955(14) 0.0375(6) Uani 1 1 d . . . . .
C51 C 0.3889(3) 0.6364(2) 0.13836(14) 0.0391(7) Uani 1 1 d . . . . .
C52 C 0.2716(3) 0.6376(2) 0.16318(15) 0.0407(7) Uani 1 1 d . . . . .
C53 C 0.1780(3) 0.7218(2) 0.17119(16) 0.0441(7) Uani 1 1 d . . . . .
H53 H 0.098545 0.722575 0.188106 0.053 Uiso 1 1 calc R U . . .
C54 C 0.1983(3) 0.8036(2) 0.15516(16) 0.0439(7) Uani 1 1 d . . . . .
C55 C 0.3149(3) 0.8014(2) 0.12959(16) 0.0449(7) Uani 1 1 d . . . . .
H55 H 0.329590 0.857519 0.118060 0.054 Uiso 1 1 calc R U . . .
C56 C 0.4108(3) 0.7191(2) 0.12039(15) 0.0423(7) Uani 1 1 d . . . . .
C57 C 0.2460(3) 0.5497(2) 0.18140(19) 0.0533(9) Uani 1 1 d . . . . .
H57A H 0.161552 0.563061 0.201990 0.080 Uiso 1 1 calc R U . . .
H57B H 0.298252 0.508365 0.212295 0.080 Uiso 1 1 calc R U . . .
H57C H 0.261430 0.520427 0.141781 0.080 Uiso 1 1 calc R U . . .
C58 C 0.0965(3) 0.8932(2) 0.16626(19) 0.0553(9) Uani 1 1 d . . . . .
H58A H 0.019789 0.882817 0.177317 0.083 Uiso 1 1 calc R U . . .
H58B H 0.096431 0.936672 0.126209 0.083 Uiso 1 1 calc R U . . .
H58C H 0.107242 0.918463 0.202463 0.083 Uiso 1 1 calc R U . . .
C59 C 0.5351(3) 0.7192(2) 0.08996(18) 0.0546(9) Uani 1 1 d . . . . .
H59A H 0.593049 0.677749 0.117955 0.082 Uiso 1 1 calc R U . . .
H59B H 0.536156 0.781417 0.085706 0.082 Uiso 1 1 calc R U . . .
H59C H 0.556906 0.698422 0.046430 0.082 Uiso 1 1 calc R U . . .
C60 C 0.7545(3) 0.34926(19) 0.17557(14) 0.0353(6) Uani 1 1 d . . . . .
C61 C 0.7664(3) 0.3450(2) 0.24165(15) 0.0393(7) Uani 1 1 d . . . . .
H61 H 0.703861 0.385068 0.269397 0.047 Uiso 1 1 calc R U . . .
C62 C 0.8659(3) 0.2845(2) 0.26623(15) 0.0413(7) Uani 1 1 d . . . . .
H62 H 0.871436 0.282808 0.310810 0.050 Uiso 1 1 calc R U . . .
C63 C 0.9608(3) 0.22437(19) 0.22617(15) 0.0388(7) Uani 1 1 d . . . . .
C64 C 1.0679(3) 0.1640(2) 0.24952(18) 0.0489(8) Uani 1 1 d . . . . .
H64 H 1.076457 0.162794 0.293507 0.059 Uiso 1 1 calc R U . . .
C65 C 1.1587(3) 0.1077(2) 0.20945(19) 0.0542(9) Uani 1 1 d . . . . .
H65 H 1.229969 0.067563 0.225620 0.065 Uiso 1 1 calc R U . . .
C66 C 1.1472(3) 0.1087(2) 0.14431(19) 0.0524(8) Uani 1 1 d . . . . .
H66 H 1.211221 0.069519 0.116623 0.063 Uiso 1 1 calc R U . . .
C67 C 1.0448(3) 0.1655(2) 0.12036(17) 0.0440(7) Uani 1 1 d . . . . .
H67 H 1.037724 0.164632 0.076455 0.053 Uiso 1 1 calc R U . . .
C68 C 0.9495(3) 0.22548(19) 0.16033(15) 0.0374(6) Uani 1 1 d . . . . .
C69 C 0.8455(3) 0.2883(2) 0.13648(14) 0.0373(6) Uani 1 1 d . . . . .
H69 H 0.837289 0.289070 0.092497 0.045 Uiso 1 1 calc R U . . .
C70 C 1.0919(3) 0.05241(19) -0.05395(14) 0.0356(6) Uani 1 1 d . . . . .
C71 C 1.1991(3) 0.0390(2) -0.09739(15) 0.0387(7) Uani 1 1 d . . . . .
C72 C 1.2020(3) 0.1270(2) -0.12387(16) 0.0420(7) Uani 1 1 d . . . . .
H72 H 1.264541 0.139738 -0.155554 0.050 Uiso 1 1 calc R U . . .
C73 C 1.0979(3) 0.1918(2) -0.09565(14) 0.0383(7) Uani 1 1 d . . . . .
C74 C 1.2945(3) -0.05085(19) -0.10909(15) 0.0387(7) Uani 1 1 d . . . . .
C75 C 1.2932(3) -0.1016(2) -0.15589(15) 0.0399(7) Uani 1 1 d . . . . .
C76 C 1.3866(3) -0.1857(2) -0.16477(16) 0.0445(7) Uani 1 1 d . . . . .
H76 H 1.384726 -0.220908 -0.195952 0.053 Uiso 1 1 calc R U . . .
C77 C 1.4812(3) -0.2195(2) -0.13010(18) 0.0483(8) Uani 1 1 d . . . . .
C78 C 1.4812(3) -0.1675(2) -0.08433(19) 0.0538(9) Uani 1 1 d . . . . .
H78 H 1.546040 -0.189243 -0.060244 0.065 Uiso 1 1 calc R U . . .
C79 C 1.3889(3) -0.0842(2) -0.07251(18) 0.0506(8) Uani 1 1 d . . . . .
C80 C 1.1953(3) -0.0658(2) -0.19768(18) 0.0491(8) Uani 1 1 d . . . . .
H80A H 1.117883 -0.062030 -0.169738 0.074 Uiso 1 1 calc R U . . .
H80B H 1.213346 -0.107507 -0.230446 0.074 Uiso 1 1 calc R U . . .
H80C H 1.191028 -0.004764 -0.219993 0.074 Uiso 1 1 calc R U . . .
C81 C 1.5816(3) -0.3099(3) -0.1420(2) 0.0671(11) Uani 1 1 d . . . . .
H81A H 1.560183 -0.340769 -0.170907 0.101 Uiso 1 1 calc R U . . .
H81B H 1.593536 -0.348843 -0.100054 0.101 Uiso 1 1 calc R U . . .
H81C H 1.656084 -0.298802 -0.162848 0.101 Uiso 1 1 calc R U . . .
C82 C 1.3889(5) -0.0303(3) -0.0207(2) 0.0802(14) Uani 1 1 d . . . . .
H82A H 1.457137 -0.065138 0.002457 0.120 Uiso 1 1 calc R U . . .
H82B H 1.313582 -0.019402 0.010746 0.120 Uiso 1 1 calc R U . . .
H82C H 1.395902 0.028581 -0.041605 0.120 Uiso 1 1 calc R U . . .
C83 C 1.0611(3) 0.29125(19) -0.10348(15) 0.0390(7) Uani 1 1 d . . . . .
C84 C 1.1133(3) 0.3364(2) -0.15995(17) 0.0483(8) Uani 1 1 d . . . . .
H84 H 1.171394 0.301338 -0.192163 0.058 Uiso 1 1 calc R U . . .
C85 C 1.0814(3) 0.4293(2) -0.16866(18) 0.0528(9) Uani 1 1 d . . . . .
H85 H 1.117366 0.457963 -0.207063 0.063 Uiso 1 1 calc R U . . .
C86 C 0.9962(3) 0.4840(2) -0.12198(17) 0.0452(7) Uani 1 1 d . . . . .
C87 C 0.9611(3) 0.5807(2) -0.1300(2) 0.0568(9) Uani 1 1 d . . . . .
H87 H 0.993824 0.611247 -0.168542 0.068 Uiso 1 1 calc R U . . .
C88 C 0.8800(3) 0.6303(2) -0.0824(2) 0.0630(10) Uani 1 1 d . . . . .
H88 H 0.857054 0.695136 -0.088141 0.076 Uiso 1 1 calc R U . . .
C89 C 0.8305(3) 0.5868(2) -0.0253(2) 0.0646(11) Uani 1 1 d . . . . .
H89 H 0.775296 0.622067 0.007627 0.077 Uiso 1 1 calc R U . . .
C90 C 0.8613(3) 0.4939(2) -0.0168(2) 0.0561(9) Uani 1 1 d . . . . .
H90 H 0.826390 0.465020 0.021909 0.067 Uiso 1 1 calc R U . . .
C91 C 0.9446(3) 0.4399(2) -0.06486(17) 0.0427(7) Uani 1 1 d . . . . .
C92 C 0.9786(3) 0.3435(2) -0.05752(16) 0.0416(7) Uani 1 1 d . . . . .
H92 H 0.943174 0.313907 -0.019457 0.050 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 H1O 0.857(19) . ?
O1 H2O 0.868(19) . ?
O2 H3O 0.849(19) . ?
O2 H4O 0.851(19) . ?
N1 C4 1.376(4) . ?
N1 C1 1.384(3) . ?
N1 H1N 0.899(18) . ?
N2 N2 1.290(4) 2_566 ?
N2 C1 1.369(4) . ?
N3 C27 1.374(4) . ?
N3 C24 1.386(3) . ?
N3 H3N 0.911(18) . ?
N4 N4 1.301(4) 2_476 ?
N4 C24 1.375(4) . ?
N5 C50 1.376(4) . ?
N5 C47 1.378(4) . ?
N5 H5N 0.900(18) . ?
N6 N6 1.288(5) 2_665 ?
N6 C47 1.371(4) . ?
N7 C73 1.375(4) . ?
N7 C70 1.379(4) . ?
N7 H7N 0.899(18) . ?
N8 N8 1.296(5) 2_755 ?
N8 C70 1.370(4) . ?
C1 C2 1.396(4) . ?
C2 C3 1.402(4) . ?
C2 C5 1.486(4) . ?
C3 C4 1.387(4) . ?
C3 H3 0.9500 . ?
C4 C14 1.456(4) . ?
C5 C6 1.396(4) . ?
C5 C10 1.396(4) . ?
C6 C7 1.399(4) . ?
C6 C11 1.505(4) . ?
C7 C8 1.386(5) . ?
C7 H7 0.9500 . ?
C8 C9 1.390(5) . ?
C8 C12 1.506(4) . ?
C9 C10 1.396(4) . ?
C9 H9 0.9500 . ?
C10 C13 1.499(5) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C23 1.381(4) . ?
C14 C15 1.412(4) . ?
C15 C16 1.371(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.418(4) . ?
C16 H16 0.9500 . ?
C17 C22 1.414(4) . ?
C17 C18 1.418(4) . ?
C18 C19 1.364(5) . ?
C18 H18 0.9500 . ?
C19 C20 1.404(5) . ?
C19 H19 0.9500 . ?
C20 C21 1.369(4) . ?
C20 H20 0.9500 . ?
C21 C22 1.419(4) . ?
C21 H21 0.9500 . ?
C22 C23 1.412(4) . ?
C23 H23 0.9500 . ?
C24 C25 1.390(4) . ?
C25 C26 1.406(4) . ?
C25 C28 1.485(4) . ?
C26 C27 1.392(4) . ?
C26 H26 0.9500 . ?
C27 C37 1.455(4) . ?
C28 C29 1.403(4) . ?
C28 C33 1.406(4) . ?
C29 C30 1.389(4) . ?
C29 C34 1.504(4) . ?
C30 C31 1.389(5) . ?
C30 H30 0.9500 . ?
C31 C32 1.381(4) . ?
C31 C35 1.513(4) . ?
C32 C33 1.393(4) . ?
C32 H32 0.9500 . ?
C33 C36 1.501(4) . ?
C34 H34A 0.9800 . ?
C34 H34B 0.9800 . ?
C34 H34C 0.9800 . ?
C35 H35A 0.9800 . ?
C35 H35B 0.9800 . ?
C35 H35C 0.9800 . ?
C36 H36A 0.9800 . ?
C36 H36B 0.9800 . ?
C36 H36C 0.9800 . ?
C37 C46 1.374(4) . ?
C37 C38 1.421(4) . ?
C38 C39 1.364(4) . ?
C38 H38 0.9500 . ?
C39 C40 1.411(4) . ?
C39 H39 0.9500 . ?
C40 C41 1.413(4) . ?
C40 C45 1.420(4) . ?
C41 C42 1.361(4) . ?
C41 H41 0.9500 . ?
C42 C43 1.402(5) . ?
C42 H42 0.9500 . ?
C43 C44 1.360(4) . ?
C43 H43 0.9500 . ?
C44 C45 1.413(4) . ?
C44 H44 0.9500 . ?
C45 C46 1.414(4) . ?
C46 H46 0.9500 . ?
C47 C48 1.389(4) . ?
C48 C49 1.403(4) . ?
C48 C51 1.480(4) . ?
C49 C50 1.393(4) . ?
C49 H49 0.9500 . ?
C50 C60 1.458(4) . ?
C51 C52 1.401(4) . ?
C51 C56 1.403(4) . ?
C52 C53 1.399(4) . ?
C52 C57 1.505(4) . ?
C53 C54 1.379(5) . ?
C53 H53 0.9500 . ?
C54 C55 1.390(5) . ?
C54 C58 1.508(4) . ?
C55 C56 1.396(4) . ?
C55 H55 0.9500 . ?
C56 C59 1.506(5) . ?
C57 H57A 0.9800 . ?
C57 H57B 0.9800 . ?
C57 H57C 0.9800 . ?
C58 H58A 0.9800 . ?
C58 H58B 0.9800 . ?
C58 H58C 0.9800 . ?
C59 H59A 0.9800 . ?
C59 H59B 0.9800 . ?
C59 H59C 0.9800 . ?
C60 C69 1.388(4) . ?
C60 C61 1.416(4) . ?
C61 C62 1.364(4) . ?
C61 H61 0.9500 . ?
C62 C63 1.413(4) . ?
C62 H62 0.9500 . ?
C63 C68 1.419(4) . ?
C63 C64 1.420(4) . ?
C64 C65 1.363(5) . ?
C64 H64 0.9500 . ?
C65 C66 1.405(5) . ?
C65 H65 0.9500 . ?
C66 C67 1.369(4) . ?
C66 H66 0.9500 . ?
C67 C68 1.413(4) . ?
C67 H67 0.9500 . ?
C68 C69 1.408(4) . ?
C69 H69 0.9500 . ?
C70 C71 1.384(4) . ?
C71 C72 1.412(4) . ?
C71 C74 1.481(4) . ?
C72 C73 1.388(4) . ?
C72 H72 0.9500 . ?
C73 C83 1.456(4) . ?
C74 C75 1.395(4) . ?
C74 C79 1.403(5) . ?
C75 C76 1.400(4) . ?
C75 C80 1.509(5) . ?
C76 C77 1.379(5) . ?
C76 H76 0.9500 . ?
C77 C78 1.385(5) . ?
C77 C81 1.513(4) . ?
C78 C79 1.396(5) . ?
C78 H78 0.9500 . ?
C79 C82 1.512(5) . ?
C80 H80A 0.9800 . ?
C80 H80B 0.9800 . ?
C80 H80C 0.9800 . ?
C81 H81A 0.9800 . ?
C81 H81B 0.9800 . ?
C81 H81C 0.9800 . ?
C82 H82A 0.9800 . ?
C82 H82B 0.9800 . ?
C82 H82C 0.9800 . ?
C83 C92 1.369(4) . ?
C83 C84 1.418(4) . ?
C84 C85 1.362(4) . ?
C84 H84 0.9500 . ?
C85 C86 1.409(5) . ?
C85 H85 0.9500 . ?
C86 C91 1.414(4) . ?
C86 C87 1.416(4) . ?
C87 C88 1.368(5) . ?
C87 H87 0.9500 . ?
C88 C89 1.398(6) . ?
C88 H88 0.9500 . ?
C89 C90 1.362(5) . ?
C89 H89 0.9500 . ?
C90 C91 1.416(4) . ?
C90 H90 0.9500 . ?
C91 C92 1.413(4) . ?
C92 H92 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
H1O O1 H2O 110(4) . . ?
H3O O2 H4O 101(4) . . ?
C4 N1 C1 109.2(2) . . ?
C4 N1 H1N 125(2) . . ?
C1 N1 H1N 125(2) . . ?
N2 N2 C1 113.4(3) 2_566 . ?
C27 N3 C24 108.9(2) . . ?
C27 N3 H3N 127(2) . . ?
C24 N3 H3N 123(2) . . ?
N4 N4 C24 113.1(3) 2_476 . ?
C50 N5 C47 109.0(2) . . ?
C50 N5 H5N 128(2) . . ?
C47 N5 H5N 123(2) . . ?
N6 N6 C47 113.8(3) 2_665 . ?
C73 N7 C70 108.8(2) . . ?
C73 N7 H7N 126(2) . . ?
C70 N7 H7N 125(2) . . ?
N8 N8 C70 113.6(3) 2_755 . ?
N2 C1 N1 126.1(2) . . ?
N2 C1 C2 125.8(2) . . ?
N1 C1 C2 108.0(2) . . ?
C1 C2 C3 106.6(2) . . ?
C1 C2 C5 124.8(3) . . ?
C3 C2 C5 128.3(3) . . ?
C4 C3 C2 108.8(3) . . ?
C4 C3 H3 125.6 . . ?
C2 C3 H3 125.6 . . ?
N1 C4 C3 107.4(2) . . ?
N1 C4 C14 123.1(2) . . ?
C3 C4 C14 129.3(3) . . ?
C6 C5 C10 120.3(3) . . ?
C6 C5 C2 120.9(3) . . ?
C10 C5 C2 118.8(3) . . ?
C5 C6 C7 118.7(3) . . ?
C5 C6 C11 121.4(3) . . ?
C7 C6 C11 119.9(3) . . ?
C8 C7 C6 122.2(3) . . ?
C8 C7 H7 118.9 . . ?
C6 C7 H7 118.9 . . ?
C7 C8 C9 117.9(3) . . ?
C7 C8 C12 121.6(3) . . ?
C9 C8 C12 120.5(3) . . ?
C8 C9 C10 121.7(3) . . ?
C8 C9 H9 119.1 . . ?
C10 C9 H9 119.1 . . ?
C9 C10 C5 119.2(3) . . ?
C9 C10 C13 119.5(3) . . ?
C5 C10 C13 121.3(3) . . ?
C6 C11 H11A 109.5 . . ?
C6 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C6 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C8 C12 H12A 109.5 . . ?
C8 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C8 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C10 C13 H13A 109.5 . . ?
C10 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C10 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C23 C14 C15 118.4(3) . . ?
C23 C14 C4 122.0(3) . . ?
C15 C14 C4 119.5(3) . . ?
C16 C15 C14 121.2(3) . . ?
C16 C15 H15 119.4 . . ?
C14 C15 H15 119.4 . . ?
C15 C16 C17 120.9(3) . . ?
C15 C16 H16 119.6 . . ?
C17 C16 H16 119.6 . . ?
C22 C17 C16 118.6(3) . . ?
C22 C17 C18 118.5(3) . . ?
C16 C17 C18 122.9(3) . . ?
C19 C18 C17 121.2(3) . . ?
C19 C18 H18 119.4 . . ?
C17 C18 H18 119.4 . . ?
C18 C19 C20 120.1(3) . . ?
C18 C19 H19 120.0 . . ?
C20 C19 H19 120.0 . . ?
C21 C20 C19 120.6(3) . . ?
C21 C20 H20 119.7 . . ?
C19 C20 H20 119.7 . . ?
C20 C21 C22 120.4(3) . . ?
C20 C21 H21 119.8 . . ?
C22 C21 H21 119.8 . . ?
C23 C22 C17 119.1(3) . . ?
C23 C22 C21 121.7(3) . . ?
C17 C22 C21 119.2(3) . . ?
C14 C23 C22 121.9(3) . . ?
C14 C23 H23 119.1 . . ?
C22 C23 H23 119.1 . . ?
N4 C24 N3 124.6(2) . . ?
N4 C24 C25 126.8(3) . . ?
N3 C24 C25 108.6(2) . . ?
C24 C25 C26 106.4(2) . . ?
C24 C25 C28 127.1(3) . . ?
C26 C25 C28 126.5(3) . . ?
C27 C26 C25 108.7(3) . . ?
C27 C26 H26 125.6 . . ?
C25 C26 H26 125.6 . . ?
N3 C27 C26 107.4(2) . . ?
N3 C27 C37 122.6(3) . . ?
C26 C27 C37 130.0(3) . . ?
C29 C28 C33 119.5(3) . . ?
C29 C28 C25 120.5(3) . . ?
C33 C28 C25 120.0(3) . . ?
C30 C29 C28 119.5(3) . . ?
C30 C29 C34 120.4(3) . . ?
C28 C29 C34 120.1(3) . . ?
C31 C30 C29 121.8(3) . . ?
C31 C30 H30 119.1 . . ?
C29 C30 H30 119.1 . . ?
C32 C31 C30 117.9(3) . . ?
C32 C31 C35 120.5(3) . . ?
C30 C31 C35 121.6(3) . . ?
C31 C32 C33 122.4(3) . . ?
C31 C32 H32 118.8 . . ?
C33 C32 H32 118.8 . . ?
C32 C33 C28 118.8(3) . . ?
C32 C33 C36 119.7(3) . . ?
C28 C33 C36 121.5(3) . . ?
C29 C34 H34A 109.5 . . ?
C29 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
C29 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C31 C35 H35A 109.5 . . ?
C31 C35 H35B 109.5 . . ?
H35A C35 H35B 109.5 . . ?
C31 C35 H35C 109.5 . . ?
H35A C35 H35C 109.5 . . ?
H35B C35 H35C 109.5 . . ?
C33 C36 H36A 109.5 . . ?
C33 C36 H36B 109.5 . . ?
H36A C36 H36B 109.5 . . ?
C33 C36 H36C 109.5 . . ?
H36A C36 H36C 109.5 . . ?
H36B C36 H36C 109.5 . . ?
C46 C37 C38 118.7(3) . . ?
C46 C37 C27 122.2(3) . . ?
C38 C37 C27 119.2(3) . . ?
C39 C38 C37 120.7(3) . . ?
C39 C38 H38 119.6 . . ?
C37 C38 H38 119.6 . . ?
C38 C39 C40 121.5(3) . . ?
C38 C39 H39 119.2 . . ?
C40 C39 H39 119.2 . . ?
C39 C40 C41 122.9(3) . . ?
C39 C40 C45 118.3(3) . . ?
C41 C40 C45 118.8(3) . . ?
C42 C41 C40 121.3(3) . . ?
C42 C41 H41 119.4 . . ?
C40 C41 H41 119.4 . . ?
C41 C42 C43 119.7(3) . . ?
C41 C42 H42 120.1 . . ?
C43 C42 H42 120.1 . . ?
C44 C43 C42 120.8(3) . . ?
C44 C43 H43 119.6 . . ?
C42 C43 H43 119.6 . . ?
C43 C44 C45 120.9(3) . . ?
C43 C44 H44 119.5 . . ?
C45 C44 H44 119.5 . . ?
C44 C45 C46 122.4(3) . . ?
C44 C45 C40 118.4(3) . . ?
C46 C45 C40 119.2(3) . . ?
C37 C46 C45 121.7(3) . . ?
C37 C46 H46 119.2 . . ?
C45 C46 H46 119.2 . . ?
N6 C47 N5 126.5(3) . . ?
N6 C47 C48 124.8(3) . . ?
N5 C47 C48 108.7(3) . . ?
C47 C48 C49 106.4(3) . . ?
C47 C48 C51 125.5(3) . . ?
C49 C48 C51 128.1(3) . . ?
C50 C49 C48 108.7(3) . . ?
C50 C49 H49 125.7 . . ?
C48 C49 H49 125.7 . . ?
N5 C50 C49 107.2(2) . . ?
N5 C50 C60 123.7(3) . . ?
C49 C50 C60 129.0(3) . . ?
C52 C51 C56 119.9(3) . . ?
C52 C51 C48 120.0(3) . . ?
C56 C51 C48 120.0(3) . . ?
C53 C52 C51 119.2(3) . . ?
C53 C52 C57 120.1(3) . . ?
C51 C52 C57 120.7(3) . . ?
C54 C53 C52 121.7(3) . . ?
C54 C53 H53 119.2 . . ?
C52 C53 H53 119.2 . . ?
C53 C54 C55 118.5(3) . . ?
C53 C54 C58 120.6(3) . . ?
C55 C54 C58 120.9(3) . . ?
C54 C55 C56 121.8(3) . . ?
C54 C55 H55 119.1 . . ?
C56 C55 H55 119.1 . . ?
C55 C56 C51 118.9(3) . . ?
C55 C56 C59 120.6(3) . . ?
C51 C56 C59 120.5(3) . . ?
C52 C57 H57A 109.5 . . ?
C52 C57 H57B 109.5 . . ?
H57A C57 H57B 109.5 . . ?
C52 C57 H57C 109.5 . . ?
H57A C57 H57C 109.5 . . ?
H57B C57 H57C 109.5 . . ?
C54 C58 H58A 109.5 . . ?
C54 C58 H58B 109.5 . . ?
H58A C58 H58B 109.5 . . ?
C54 C58 H58C 109.5 . . ?
H58A C58 H58C 109.5 . . ?
H58B C58 H58C 109.5 . . ?
C56 C59 H59A 109.5 . . ?
C56 C59 H59B 109.5 . . ?
H59A C59 H59B 109.5 . . ?
C56 C59 H59C 109.5 . . ?
H59A C59 H59C 109.5 . . ?
H59B C59 H59C 109.5 . . ?
C69 C60 C61 118.3(3) . . ?
C69 C60 C50 121.8(3) . . ?
C61 C60 C50 119.8(3) . . ?
C62 C61 C60 121.3(3) . . ?
C62 C61 H61 119.4 . . ?
C60 C61 H61 119.4 . . ?
C61 C62 C63 120.8(3) . . ?
C61 C62 H62 119.6 . . ?
C63 C62 H62 119.6 . . ?
C62 C63 C68 119.0(3) . . ?
C62 C63 C64 122.0(3) . . ?
C68 C63 C64 119.0(3) . . ?
C65 C64 C63 120.6(3) . . ?
C65 C64 H64 119.7 . . ?
C63 C64 H64 119.7 . . ?
C64 C65 C66 120.3(3) . . ?
C64 C65 H65 119.9 . . ?
C66 C65 H65 119.9 . . ?
C67 C66 C65 120.6(3) . . ?
C67 C66 H66 119.7 . . ?
C65 C66 H66 119.7 . . ?
C66 C67 C68 120.6(3) . . ?
C66 C67 H67 119.7 . . ?
C68 C67 H67 119.7 . . ?
C69 C68 C67 122.3(3) . . ?
C69 C68 C63 118.9(3) . . ?
C67 C68 C63 118.8(3) . . ?
C60 C69 C68 121.7(3) . . ?
C60 C69 H69 119.2 . . ?
C68 C69 H69 119.2 . . ?
N8 C70 N7 125.5(3) . . ?
N8 C70 C71 125.7(3) . . ?
N7 C70 C71 108.8(2) . . ?
C70 C71 C72 106.5(3) . . ?
C70 C71 C74 125.8(3) . . ?
C72 C71 C74 127.6(3) . . ?
C73 C72 C71 108.3(3) . . ?
C73 C72 H72 125.9 . . ?
C71 C72 H72 125.9 . . ?
N7 C73 C72 107.6(3) . . ?
N7 C73 C83 122.4(3) . . ?
C72 C73 C83 129.9(3) . . ?
C75 C74 C79 119.8(3) . . ?
C75 C74 C71 121.6(3) . . ?
C79 C74 C71 118.5(3) . . ?
C74 C75 C76 118.7(3) . . ?
C74 C75 C80 121.0(3) . . ?
C76 C75 C80 120.3(3) . . ?
C77 C76 C75 122.7(3) . . ?
C77 C76 H76 118.7 . . ?
C75 C76 H76 118.7 . . ?
C76 C77 C78 117.7(3) . . ?
C76 C77 C81 121.0(3) . . ?
C78 C77 C81 121.3(3) . . ?
C77 C78 C79 122.0(3) . . ?
C77 C78 H78 119.0 . . ?
C79 C78 H78 119.0 . . ?
C78 C79 C74 119.2(3) . . ?
C78 C79 C82 121.0(3) . . ?
C74 C79 C82 119.9(3) . . ?
C75 C80 H80A 109.5 . . ?
C75 C80 H80B 109.5 . . ?
H80A C80 H80B 109.5 . . ?
C75 C80 H80C 109.5 . . ?
H80A C80 H80C 109.5 . . ?
H80B C80 H80C 109.5 . . ?
C77 C81 H81A 109.5 . . ?
C77 C81 H81B 109.5 . . ?
H81A C81 H81B 109.5 . . ?
C77 C81 H81C 109.5 . . ?
H81A C81 H81C 109.5 . . ?
H81B C81 H81C 109.5 . . ?
C79 C82 H82A 109.5 . . ?
C79 C82 H82B 109.5 . . ?
H82A C82 H82B 109.5 . . ?
C79 C82 H82C 109.5 . . ?
H82A C82 H82C 109.5 . . ?
H82B C82 H82C 109.5 . . ?
C92 C83 C84 118.2(3) . . ?
C92 C83 C73 122.4(3) . . ?
C84 C83 C73 119.4(3) . . ?
C85 C84 C83 120.9(3) . . ?
C85 C84 H84 119.5 . . ?
C83 C84 H84 119.5 . . ?
C84 C85 C86 121.5(3) . . ?
C84 C85 H85 119.3 . . ?
C86 C85 H85 119.3 . . ?
C85 C86 C91 118.4(3) . . ?
C85 C86 C87 122.6(3) . . ?
C91 C86 C87 119.1(3) . . ?
C88 C87 C86 120.1(3) . . ?
C88 C87 H87 119.9 . . ?
C86 C87 H87 119.9 . . ?
C87 C88 C89 120.9(3) . . ?
C87 C88 H88 119.5 . . ?
C89 C88 H88 119.5 . . ?
C90 C89 C88 120.2(4) . . ?
C90 C89 H89 119.9 . . ?
C88 C89 H89 119.9 . . ?
C89 C90 C91 120.8(3) . . ?
C89 C90 H90 119.6 . . ?
C91 C90 H90 119.6 . . ?
C92 C91 C86 118.8(3) . . ?
C92 C91 C90 122.3(3) . . ?
C86 C91 C90 118.9(3) . . ?
C83 C92 C91 122.2(3) . . ?
C83 C92 H92 118.9 . . ?
C91 C92 H92 118.9 . . ?

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
N2 N2 C1 N1 0.6(5) 2_566 . . . ?
N2 N2 C1 C2 178.9(3) 2_566 . . . ?
C4 N1 C1 N2 178.4(3) . . . . ?
C4 N1 C1 C2 -0.2(3) . . . . ?
N2 C1 C2 C3 -178.8(3) . . . . ?
N1 C1 C2 C3 -0.2(3) . . . . ?
N2 C1 C2 C5 -4.1(5) . . . . ?
N1 C1 C2 C5 174.5(3) . . . . ?
C1 C2 C3 C4 0.5(3) . . . . ?
C5 C2 C3 C4 -174.0(3) . . . . ?
C1 N1 C4 C3 0.5(3) . . . . ?
C1 N1 C4 C14 -174.4(3) . . . . ?
C2 C3 C4 N1 -0.6(3) . . . . ?
C2 C3 C4 C14 173.9(3) . . . . ?
C1 C2 C5 C6 96.0(4) . . . . ?
C3 C2 C5 C6 -90.4(4) . . . . ?
C1 C2 C5 C10 -83.8(4) . . . . ?
C3 C2 C5 C10 89.7(4) . . . . ?
C10 C5 C6 C7 1.2(4) . . . . ?
C2 C5 C6 C7 -178.7(3) . . . . ?
C10 C5 C6 C11 -179.0(3) . . . . ?
C2 C5 C6 C11 1.2(4) . . . . ?
C5 C6 C7 C8 -0.5(4) . . . . ?
C11 C6 C7 C8 179.6(3) . . . . ?
C6 C7 C8 C9 -0.4(5) . . . . ?
C6 C7 C8 C12 -179.0(3) . . . . ?
C7 C8 C9 C10 0.6(5) . . . . ?
C12 C8 C9 C10 179.3(3) . . . . ?
C8 C9 C10 C5 0.1(5) . . . . ?
C8 C9 C10 C13 -179.3(3) . . . . ?
C6 C5 C10 C9 -1.0(4) . . . . ?
C2 C5 C10 C9 178.9(3) . . . . ?
C6 C5 C10 C13 178.4(3) . . . . ?
C2 C5 C10 C13 -1.8(5) . . . . ?
N1 C4 C14 C23 18.8(4) . . . . ?
C3 C4 C14 C23 -154.9(3) . . . . ?
N1 C4 C14 C15 -163.7(3) . . . . ?
C3 C4 C14 C15 22.6(5) . . . . ?
C23 C14 C15 C16 0.9(4) . . . . ?
C4 C14 C15 C16 -176.7(3) . . . . ?
C14 C15 C16 C17 -0.8(4) . . . . ?
C15 C16 C17 C22 0.0(4) . . . . ?
C15 C16 C17 C18 -179.8(3) . . . . ?
C22 C17 C18 C19 0.5(4) . . . . ?
C16 C17 C18 C19 -179.8(3) . . . . ?
C17 C18 C19 C20 -0.6(5) . . . . ?
C18 C19 C20 C21 0.5(5) . . . . ?
C19 C20 C21 C22 -0.2(5) . . . . ?
C16 C17 C22 C23 0.8(4) . . . . ?
C18 C17 C22 C23 -179.5(3) . . . . ?
C16 C17 C22 C21 -180.0(3) . . . . ?
C18 C17 C22 C21 -0.2(4) . . . . ?
C20 C21 C22 C23 179.3(3) . . . . ?
C20 C21 C22 C17 0.1(4) . . . . ?
C15 C14 C23 C22 -0.1(4) . . . . ?
C4 C14 C23 C22 177.4(3) . . . . ?
C17 C22 C23 C14 -0.7(4) . . . . ?
C21 C22 C23 C14 -179.9(3) . . . . ?
N4 N4 C24 N3 0.5(5) 2_476 . . . ?
N4 N4 C24 C25 -178.1(3) 2_476 . . . ?
C27 N3 C24 N4 -178.7(3) . . . . ?
C27 N3 C24 C25 0.2(3) . . . . ?
N4 C24 C25 C26 179.0(3) . . . . ?
N3 C24 C25 C26 0.1(3) . . . . ?
N4 C24 C25 C28 -0.3(5) . . . . ?
N3 C24 C25 C28 -179.1(3) . . . . ?
C24 C25 C26 C27 -0.4(3) . . . . ?
C28 C25 C26 C27 178.9(3) . . . . ?
C24 N3 C27 C26 -0.4(3) . . . . ?
C24 N3 C27 C37 -179.2(3) . . . . ?
C25 C26 C27 N3 0.5(3) . . . . ?
C25 C26 C27 C37 179.2(3) . . . . ?
C24 C25 C28 C29 -104.1(4) . . . . ?
C26 C25 C28 C29 76.8(4) . . . . ?
C24 C25 C28 C33 79.0(4) . . . . ?
C26 C25 C28 C33 -100.1(4) . . . . ?
C33 C28 C29 C30 0.8(4) . . . . ?
C25 C28 C29 C30 -176.1(3) . . . . ?
C33 C28 C29 C34 179.9(3) . . . . ?
C25 C28 C29 C34 3.0(4) . . . . ?
C28 C29 C30 C31 -0.9(5) . . . . ?
C34 C29 C30 C31 -180.0(3) . . . . ?
C29 C30 C31 C32 0.5(5) . . . . ?
C29 C30 C31 C35 179.9(3) . . . . ?
C30 C31 C32 C33 0.0(5) . . . . ?
C35 C31 C32 C33 -179.4(3) . . . . ?
C31 C32 C33 C28 -0.1(4) . . . . ?
C31 C32 C33 C36 179.3(3) . . . . ?
C29 C28 C33 C32 -0.3(4) . . . . ?
C25 C28 C33 C32 176.6(3) . . . . ?
C29 C28 C33 C36 -179.7(3) . . . . ?
C25 C28 C33 C36 -2.8(4) . . . . ?
N3 C27 C37 C46 6.4(5) . . . . ?
C26 C27 C37 C46 -172.1(3) . . . . ?
N3 C27 C37 C38 -173.0(3) . . . . ?
C26 C27 C37 C38 8.5(5) . . . . ?
C46 C37 C38 C39 0.2(5) . . . . ?
C27 C37 C38 C39 179.7(3) . . . . ?
C37 C38 C39 C40 -0.4(5) . . . . ?
C38 C39 C40 C41 -178.8(3) . . . . ?
C38 C39 C40 C45 0.9(5) . . . . ?
C39 C40 C41 C42 179.2(3) . . . . ?
C45 C40 C41 C42 -0.6(5) . . . . ?
C40 C41 C42 C43 1.3(5) . . . . ?
C41 C42 C43 C44 -1.1(5) . . . . ?
C42 C43 C44 C45 0.2(5) . . . . ?
C43 C44 C45 C46 -178.3(3) . . . . ?
C43 C44 C45 C40 0.5(5) . . . . ?
C39 C40 C45 C44 179.9(3) . . . . ?
C41 C40 C45 C44 -0.4(4) . . . . ?
C39 C40 C45 C46 -1.2(4) . . . . ?
C41 C40 C45 C46 178.5(3) . . . . ?
C38 C37 C46 C45 -0.5(5) . . . . ?
C27 C37 C46 C45 -180.0(3) . . . . ?
C44 C45 C46 C37 179.9(3) . . . . ?
C40 C45 C46 C37 1.0(5) . . . . ?
N6 N6 C47 N5 1.0(5) 2_665 . . . ?
N6 N6 C47 C48 -179.9(3) 2_665 . . . ?
C50 N5 C47 N6 179.1(3) . . . . ?
C50 N5 C47 C48 -0.2(3) . . . . ?
N6 C47 C48 C49 -179.7(3) . . . . ?
N5 C47 C48 C49 -0.5(4) . . . . ?
N6 C47 C48 C51 -0.5(5) . . . . ?
N5 C47 C48 C51 178.8(3) . . . . ?
C47 C48 C49 C50 0.9(4) . . . . ?
C51 C48 C49 C50 -178.3(3) . . . . ?
C47 N5 C50 C49 0.8(3) . . . . ?
C47 N5 C50 C60 -175.7(3) . . . . ?
C48 C49 C50 N5 -1.1(4) . . . . ?
C48 C49 C50 C60 175.2(3) . . . . ?
C47 C48 C51 C52 87.6(4) . . . . ?
C49 C48 C51 C52 -93.3(4) . . . . ?
C47 C48 C51 C56 -92.9(4) . . . . ?
C49 C48 C51 C56 86.1(4) . . . . ?
C56 C51 C52 C53 -1.6(4) . . . . ?
C48 C51 C52 C53 177.9(3) . . . . ?
C56 C51 C52 C57 178.7(3) . . . . ?
C48 C51 C52 C57 -1.8(4) . . . . ?
C51 C52 C53 C54 0.1(5) . . . . ?
C57 C52 C53 C54 179.8(3) . . . . ?
C52 C53 C54 C55 0.9(5) . . . . ?
C52 C53 C54 C58 -178.1(3) . . . . ?
C53 C54 C55 C56 -0.5(5) . . . . ?
C58 C54 C55 C56 178.5(3) . . . . ?
C54 C55 C56 C51 -0.9(5) . . . . ?
C54 C55 C56 C59 177.4(3) . . . . ?
C52 C51 C56 C55 1.9(4) . . . . ?
C48 C51 C56 C55 -177.5(3) . . . . ?
C52 C51 C56 C59 -176.4(3) . . . . ?
C48 C51 C56 C59 4.2(4) . . . . ?
N5 C50 C60 C69 10.7(5) . . . . ?
C49 C50 C60 C69 -164.9(3) . . . . ?
N5 C50 C60 C61 -172.2(3) . . . . ?
C49 C50 C60 C61 12.1(5) . . . . ?
C69 C60 C61 C62 1.8(4) . . . . ?
C50 C60 C61 C62 -175.4(3) . . . . ?
C60 C61 C62 C63 0.4(5) . . . . ?
C61 C62 C63 C68 -2.1(5) . . . . ?
C61 C62 C63 C64 176.8(3) . . . . ?
C62 C63 C64 C65 -179.1(3) . . . . ?
C68 C63 C64 C65 -0.1(5) . . . . ?
C63 C64 C65 C66 0.0(5) . . . . ?
C64 C65 C66 C67 -0.5(5) . . . . ?
C65 C66 C67 C68 1.2(5) . . . . ?
C66 C67 C68 C69 176.6(3) . . . . ?
C66 C67 C68 C63 -1.3(5) . . . . ?
C62 C63 C68 C69 1.8(4) . . . . ?
C64 C63 C68 C69 -177.2(3) . . . . ?
C62 C63 C68 C67 179.7(3) . . . . ?
C64 C63 C68 C67 0.8(4) . . . . ?
C61 C60 C69 C68 -2.1(4) . . . . ?
C50 C60 C69 C68 175.0(3) . . . . ?
C67 C68 C69 C60 -177.5(3) . . . . ?
C63 C68 C69 C60 0.4(4) . . . . ?
N8 N8 C70 N7 1.0(5) 2_755 . . . ?
N8 N8 C70 C71 -178.7(3) 2_755 . . . ?
C73 N7 C70 N8 -179.4(3) . . . . ?
C73 N7 C70 C71 0.4(3) . . . . ?
N8 C70 C71 C72 179.1(3) . . . . ?
N7 C70 C71 C72 -0.6(3) . . . . ?
N8 C70 C71 C74 -5.0(5) . . . . ?
N7 C70 C71 C74 175.3(3) . . . . ?
C70 C71 C72 C73 0.7(4) . . . . ?
C74 C71 C72 C73 -175.1(3) . . . . ?
C70 N7 C73 C72 0.1(3) . . . . ?
C70 N7 C73 C83 -176.9(3) . . . . ?
C71 C72 C73 N7 -0.4(4) . . . . ?
C71 C72 C73 C83 176.2(3) . . . . ?
C70 C71 C74 C75 88.3(4) . . . . ?
C72 C71 C74 C75 -96.7(4) . . . . ?
C70 C71 C74 C79 -92.6(4) . . . . ?
C72 C71 C74 C79 82.4(4) . . . . ?
C79 C74 C75 C76 0.5(4) . . . . ?
C71 C74 C75 C76 179.6(3) . . . . ?
C79 C74 C75 C80 -177.8(3) . . . . ?
C71 C74 C75 C80 1.3(4) . . . . ?
C74 C75 C76 C77 -1.4(5) . . . . ?
C80 C75 C76 C77 176.9(3) . . . . ?
C75 C76 C77 C78 0.8(5) . . . . ?
C75 C76 C77 C81 -178.9(3) . . . . ?
C76 C77 C78 C79 0.7(5) . . . . ?
C81 C77 C78 C79 -179.6(3) . . . . ?
C77 C78 C79 C74 -1.5(5) . . . . ?
C77 C78 C79 C82 177.9(4) . . . . ?
C75 C74 C79 C78 0.9(5) . . . . ?
C71 C74 C79 C78 -178.2(3) . . . . ?
C75 C74 C79 C82 -178.6(3) . . . . ?
C71 C74 C79 C82 2.3(5) . . . . ?
N7 C73 C83 C92 18.9(5) . . . . ?
C72 C73 C83 C92 -157.3(3) . . . . ?
N7 C73 C83 C84 -162.2(3) . . . . ?
C72 C73 C83 C84 21.5(5) . . . . ?
C92 C83 C84 C85 -0.7(5) . . . . ?
C73 C83 C84 C85 -179.6(3) . . . . ?
C83 C84 C85 C86 0.4(6) . . . . ?
C84 C85 C86 C91 0.6(6) . . . . ?
C84 C85 C86 C87 -179.7(4) . . . . ?
C85 C86 C87 C88 -178.4(4) . . . . ?
C91 C86 C87 C88 1.3(6) . . . . ?
C86 C87 C88 C89 -0.1(6) . . . . ?
C87 C88 C89 C90 -1.0(6) . . . . ?
C88 C89 C90 C91 0.8(6) . . . . ?
C85 C86 C91 C92 -1.2(5) . . . . ?
C87 C86 C91 C92 179.1(3) . . . . ?
C85 C86 C91 C90 178.3(3) . . . . ?
C87 C86 C91 C90 -1.4(5) . . . . ?
C89 C90 C91 C92 179.9(4) . . . . ?
C89 C90 C91 C86 0.4(6) . . . . ?
C84 C83 C92 C91 0.1(5) . . . . ?
C73 C83 C92 C91 179.0(3) . . . . ?
C86 C91 C92 C83 0.9(5) . . . . ?
C90 C91 C92 C83 -178.6(3) . . . . ?

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
N1 H1N O1 0.899(18) 2.232(19) 3.121(3) 170(3) . yes
N3 H3N O1 0.911(18) 2.373(19) 3.274(3) 171(3) . yes
N5 H5N O2 0.900(18) 2.261(19) 3.152(3) 171(3) . yes
N7 H7N O2 0.899(18) 2.30(2) 3.192(4) 170(3) . yes

_refine_diff_density_max         0.325
_refine_diff_density_min         -0.324
_refine_diff_density_rms         0.066

####################################################################### 
# 
# 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_AT020_MD2
_database_code_depnum_ccdc_archive 'CCDC 2442945'
loop_
_audit_author_name
_audit_author_address
'Katherine Robertson'
;Saint Marys University
Canada
;
_audit_update_record             
;
2025-04-10 deposited with the CCDC.	2025-07-29 downloaded from the CCDC.
;

#==============================================================================

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C46 H40 N4, C H Cl3'
_chemical_formula_sum            'C47 H41 Cl3 N4'
_chemical_formula_weight         768.19

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   11.3441(8)
_cell_length_b                   12.4064(9)
_cell_length_c                   14.9314(11)
_cell_angle_alpha                90.660(3)
_cell_angle_beta                 90.394(3)
_cell_angle_gamma                112.630(3)
_cell_volume                     1939.4(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9274
_cell_measurement_theta_min      2.2249
_cell_measurement_theta_max      30.3893

_exptl_crystal_description       plate
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.315
_exptl_crystal_F_000             804
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.261
_exptl_crystal_size_mid          0.156
_exptl_crystal_size_min          0.035
_exptl_absorpt_coefficient_mu    0.276
_shelx_estimated_absorpt_T_min   0.931
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7100
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_process_details   
;
Krause, L., Herbst-Irmer, R., Sheldrick, G. M., Stalke, D. (2015).
J. Appl. Cryst. 48, 3-10.
;
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_source_type              'Incoatec I\mS 3.0'
_diffrn_source_source            'microfocus sealed tube'
_diffrn_source_power             0.07
_diffrn_source_current           1.4
_diffrn_source_voltage           50
_diffrn_radiation_monochromator  'multilayer mirror'
_diffrn_measurement_device       'κ--geometry diffractometer'
_diffrn_detector_type            'Bruker PHOTON III'
_diffrn_detector                 '100 \\times 140 mm^2^ CMOS sensor'
_diffrn_detector_area_resol_mean 7.3910
_diffrn_reflns_number            110441
_diffrn_reflns_av_unetI/netI     0.0230
_diffrn_reflns_av_R_equivalents  0.0410
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.779
_diffrn_reflns_theta_max         30.540
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             11834
_reflns_number_gt                9147
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker Instrument Service v8.5.0.11 RC8'
_computing_cell_refinement       'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_data_reduction        'SAINT V8.40B (Bruker AXS LLC, 2019)'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1167P)²+1.2072P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     'dual space'
_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         11834
_refine_ls_number_parameters     692
_refine_ls_number_restraints     966
_refine_ls_R_factor_all          0.0829
_refine_ls_R_factor_gt           0.0635
_refine_ls_wR_factor_ref         0.2113
_refine_ls_wR_factor_gt          0.1872
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.029
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.77334(12) 0.44634(13) 0.04051(9) 0.0231(3) Uani 1 1 d D . . . .
H1N H 0.767(2) 0.443(2) -0.0182(11) 0.035 Uiso 1 1 d D U . . .
N2 N 1.00522(12) 0.51088(12) 0.04253(9) 0.0229(3) Uani 1 1 d . . . . .
N3 N 0.11699(14) 0.05187(14) 0.14466(10) 0.0276(3) Uani 1 1 d D . . . .
H3N H 0.183(2) 0.049(2) 0.1115(17) 0.041 Uiso 1 1 d D U . . .
N4 N -0.04496(14) -0.00015(13) 0.02616(10) 0.0281(3) Uani 1 1 d . . . . .
C1 C 0.89018(14) 0.48749(14) 0.08331(10) 0.0221(3) Uani 1 1 d . . . . .
C2 C 0.87044(14) 0.49992(14) 0.17438(10) 0.0225(3) Uani 1 1 d . . . . .
C3 C 0.73744(14) 0.46624(15) 0.18448(11) 0.0244(3) Uani 1 1 d . . . . .
H3 H 0.695105 0.465670 0.239251 0.029 Uiso 1 1 calc R U . . .
C4 C 0.67889(14) 0.43413(14) 0.10108(10) 0.0223(3) Uani 1 1 d . . . . .
C5 C 0.96847(14) 0.54345(15) 0.24619(11) 0.0243(3) Uani 1 1 d . . . . .
C6 C 0.97680(17) 0.46848(17) 0.31329(11) 0.0304(3) Uani 1 1 d . . . . .
C7 C 1.0677(2) 0.5124(2) 0.38144(13) 0.0384(4) Uani 1 1 d . . . . .
H7 H 1.071891 0.461987 0.427642 0.046 Uiso 1 1 calc R U . . .
C8 C 1.1524(2) 0.6284(2) 0.38348(14) 0.0418(5) Uani 1 1 d . . . . .
C9 C 1.14153(19) 0.70171(19) 0.31747(15) 0.0384(4) Uani 1 1 d . . . . .
H9 H 1.197921 0.781547 0.318935 0.046 Uiso 1 1 calc R U . . .
C10 C 1.05046(16) 0.66177(16) 0.24912(12) 0.0290(3) Uani 1 1 d . . . . .
C11 C 0.8919(2) 0.3400(2) 0.31198(16) 0.0472(5) Uani 1 1 d . . . . .
H11A H 0.919858 0.300378 0.359003 0.071 Uiso 1 1 calc R U . . .
H11B H 0.897390 0.305694 0.253492 0.071 Uiso 1 1 calc R U . . .
H11C H 0.803337 0.330668 0.322592 0.071 Uiso 1 1 calc R U . . .
C12 C 1.2549(3) 0.6731(3) 0.45515(19) 0.0628(8) Uani 1 1 d . . . . .
H12A H 1.335863 0.674681 0.431415 0.094 Uiso 1 1 calc R U . . .
H12B H 1.230497 0.621448 0.506832 0.094 Uiso 1 1 calc R U . . .
H12C H 1.264881 0.752180 0.473744 0.094 Uiso 1 1 calc R U . . .
C13 C 1.0383(2) 0.74551(19) 0.18087(17) 0.0431(5) Uani 1 1 d . . . . .
H13A H 1.080425 0.825747 0.203790 0.065 Uiso 1 1 calc R U . . .
H13B H 0.947686 0.728694 0.169377 0.065 Uiso 1 1 calc R U . . .
H13C H 1.078722 0.736547 0.125036 0.065 Uiso 1 1 calc R U . . .
C14 C 0.54393(14) 0.38720(15) 0.07342(11) 0.0233(3) Uani 1 1 d . . . . .
C15 C 0.50271(16) 0.30057(16) 0.00836(12) 0.0288(3) Uani 1 1 d . . . . .
H15 H 0.563321 0.275841 -0.019431 0.035 Uiso 1 1 calc R U . . .
C16 C 0.37336(18) 0.24761(17) -0.01815(13) 0.0337(4) Uani 1 1 d . . . . .
H16 H 0.347832 0.188386 -0.063406 0.040 Uiso 1 1 calc R U . . .
C17 C 0.28453(16) 0.28175(17) 0.02149(13) 0.0312(4) Uani 1 1 d . . . . .
H17 H 0.197306 0.245685 0.003727 0.037 Uiso 1 1 calc R U . . .
C18 C 0.32151(15) 0.37022(15) 0.08864(11) 0.0258(3) Uani 1 1 d . . . . .
C19 C 0.22958(16) 0.40396(18) 0.13149(13) 0.0324(4) Uani 1 1 d . . . . .
H19 H 0.141873 0.365215 0.115732 0.039 Uiso 1 1 calc R U . . .
C20 C 0.26462(18) 0.49081(19) 0.19478(14) 0.0358(4) Uani 1 1 d . . . . .
H20 H 0.201739 0.511995 0.223082 0.043 Uiso 1 1 calc R U . . .
C21 C 0.39460(18) 0.54909(18) 0.21807(13) 0.0337(4) Uani 1 1 d . . . . .
H21 H 0.418975 0.610650 0.261426 0.040 Uiso 1 1 calc R U . . .
C22 C 0.48662(16) 0.51823(16) 0.17903(12) 0.0275(3) Uani 1 1 d . . . . .
H22 H 0.573819 0.559060 0.195326 0.033 Uiso 1 1 calc R U . . .
C23 C 0.45275(14) 0.42593(14) 0.11459(11) 0.0229(3) Uani 1 1 d . . . . .
C24 C -0.00501(16) 0.02805(15) 0.11326(11) 0.0270(3) Uani 1 1 d . . . . .
C25 C -0.07974(17) 0.03509(16) 0.18509(12) 0.0286(3) Uani 1 1 d . . . . .
C26 C 0.00148(18) 0.06252(17) 0.26136(12) 0.0314(4) Uani 1 1 d . . . . .
H26 H -0.022493 0.073150 0.320624 0.038 Uiso 1 1 calc R U . . .
C27 C 0.12190(17) 0.07136(16) 0.23541(11) 0.0288(3) Uani 1 1 d . . . . .
C28A C -0.2170(4) 0.0128(3) 0.1787(3) 0.0290(5) Uani 0.883(7) 1 d D U P A 1
C29A C -0.2616(2) 0.0823(2) 0.12561(18) 0.0312(5) Uani 0.883(7) 1 d D U P A 1
C30A C -0.3927(2) 0.0536(3) 0.11767(19) 0.0368(6) Uani 0.883(7) 1 d D U P A 1
H30A H -0.422390 0.101611 0.082538 0.044 Uiso 0.883(7) 1 calc R U P A 1
C31A C -0.4817(2) -0.0430(3) 0.15943(19) 0.0404(6) Uani 0.883(7) 1 d D U P A 1
C32A C -0.4364(3) -0.1092(3) 0.2139(2) 0.0394(6) Uani 0.883(7) 1 d D U P A 1
H32A H -0.495613 -0.172835 0.245577 0.047 Uiso 0.883(7) 1 calc R U P A 1
C33A C -0.3048(3) -0.0840(4) 0.2233(4) 0.0343(6) Uani 0.883(7) 1 d D U P A 1
C34A C -0.1711(3) 0.1872(3) 0.0767(2) 0.0384(6) Uani 0.883(7) 1 d D U P A 1
H34A H -0.094884 0.227173 0.113935 0.058 Uiso 0.883(7) 1 calc R U P A 1
H34B H -0.213644 0.240965 0.064257 0.058 Uiso 0.883(7) 1 calc R U P A 1
H34C H -0.146234 0.161554 0.020139 0.058 Uiso 0.883(7) 1 calc R U P A 1
C35A C -0.6239(3) -0.0768(3) 0.1422(3) 0.0620(10) Uani 0.883(7) 1 d D U P A 1
H35A H -0.665901 -0.161981 0.136461 0.093 Uiso 0.883(7) 1 calc R U P A 1
H35B H -0.636425 -0.040931 0.086737 0.093 Uiso 0.883(7) 1 calc R U P A 1
H35C H -0.660851 -0.049395 0.192330 0.093 Uiso 0.883(7) 1 calc R U P A 1
C36A C -0.2628(4) -0.1656(4) 0.2749(3) 0.0440(8) Uani 0.883(7) 1 d D U P A 1
H36A H -0.337796 -0.229265 0.298064 0.066 Uiso 0.883(7) 1 calc R U P A 1
H36B H -0.207524 -0.123172 0.325015 0.066 Uiso 0.883(7) 1 calc R U P A 1
H36C H -0.215428 -0.198016 0.235533 0.066 Uiso 0.883(7) 1 calc R U P A 1
C28B C -0.217(3) 0.020(2) 0.182(2) 0.034(2) Uani 0.117(7) 1 d D U P A 2
C29B C -0.2439(17) 0.1104(19) 0.1421(14) 0.037(2) Uani 0.117(7) 1 d D U P A 2
C30B C -0.3693(15) 0.0959(18) 0.1445(13) 0.039(2) Uani 0.117(7) 1 d D U P A 2
H30B H -0.386987 0.158167 0.119462 0.047 Uiso 0.117(7) 1 calc R U P A 2
C31B C -0.4754(14) 0.006(2) 0.1774(14) 0.043(2) Uani 0.117(7) 1 d D U P A 2
C32B C -0.444(2) -0.080(2) 0.2197(18) 0.041(3) Uani 0.117(7) 1 d D U P A 2
H32B H -0.509250 -0.142811 0.247793 0.049 Uiso 0.117(7) 1 calc R U P A 2
C33B C -0.318(3) -0.074(3) 0.222(3) 0.037(3) Uani 0.117(7) 1 d D U P A 2
C34B C -0.136(2) 0.206(3) 0.0943(18) 0.059(7) Uani 0.117(7) 1 d D U P A 2
H34D H -0.111552 0.173349 0.041146 0.089 Uiso 0.117(7) 1 calc R U P A 2
H34E H -0.062449 0.239814 0.134948 0.089 Uiso 0.117(7) 1 calc R U P A 2
H34F H -0.165503 0.267730 0.076181 0.089 Uiso 0.117(7) 1 calc R U P A 2
C35B C -0.6105(19) -0.007(4) 0.159904 0.088(7) Uani 0.117(7) 1 d D U P A 2
H35D H -0.617569 0.068159 0.168975 0.132 Uiso 0.117(7) 1 calc R U P A 2
H35E H -0.667335 -0.064341 0.201256 0.132 Uiso 0.117(7) 1 calc R U P A 2
H35F H -0.634867 -0.034703 0.098074 0.132 Uiso 0.117(7) 1 calc R U P A 2
C36B C -0.294(4) -0.171(3) 0.265(4) 0.063(7) Uani 0.117(7) 1 d D U P A 2
H36D H -0.375478 -0.231056 0.282945 0.094 Uiso 0.117(7) 1 calc R U P A 2
H36E H -0.239046 -0.140890 0.317821 0.094 Uiso 0.117(7) 1 calc R U P A 2
H36F H -0.251840 -0.205000 0.222514 0.094 Uiso 0.117(7) 1 calc R U P A 2
C37 C 0.24259(17) 0.10045(16) 0.28556(12) 0.0302(3) Uani 1 1 d . . . . .
C38 C 0.35524(19) 0.17063(18) 0.24523(14) 0.0369(4) Uani 1 1 d . . . . .
H38 H 0.352585 0.197507 0.186222 0.044 Uiso 1 1 calc R U . . .
C39 C 0.4740(2) 0.2029(2) 0.29040(17) 0.0468(5) Uani 1 1 d . . . . .
H39 H 0.550170 0.250303 0.261271 0.056 Uiso 1 1 calc R U . . .
C40 C 0.4800(2) 0.1663(2) 0.37574(16) 0.0458(5) Uani 1 1 d . . . . .
H40 H 0.560076 0.190341 0.406158 0.055 Uiso 1 1 calc R U . . .
C41 C 0.3673(2) 0.09255(19) 0.41911(13) 0.0376(4) Uani 1 1 d . . . . .
C42 C 0.3723(2) 0.0522(2) 0.50717(15) 0.0456(5) Uani 1 1 d . . . . .
H42 H 0.451763 0.078342 0.538575 0.055 Uiso 1 1 calc R U . . .
C43 C 0.2653(3) -0.0234(2) 0.54751(14) 0.0474(5) Uani 1 1 d . . . . .
H43 H 0.270366 -0.049490 0.606422 0.057 Uiso 1 1 calc R U . . .
C44 C 0.1475(2) -0.0623(2) 0.50136(14) 0.0450(5) Uani 1 1 d . . . . .
H44 H 0.073425 -0.116484 0.528836 0.054 Uiso 1 1 calc R U . . .
C45 C 0.1382(2) -0.0230(2) 0.41706(13) 0.0374(4) Uani 1 1 d . . . . .
H45 H 0.057444 -0.049739 0.387387 0.045 Uiso 1 1 calc R U . . .
C46 C 0.24603(18) 0.05630(17) 0.37380(12) 0.0310(4) Uani 1 1 d . . . . .
C47A C 0.7250(8) 0.6718(13) 0.4773(6) 0.043(2) Uani 0.528(13) 1 d D U P B 1
H47A H 0.716915 0.749048 0.472872 0.051 Uiso 0.528(13) 1 calc R U P B 1
Cl1A Cl 0.7208(3) 0.6382(4) 0.5910(3) 0.0449(7) Uani 0.528(13) 1 d D U P B 1
Cl2A Cl 0.8730(4) 0.6877(4) 0.4320(3) 0.0492(8) Uani 0.528(13) 1 d D U P B 1
Cl3A Cl 0.6011(4) 0.5717(4) 0.41491(18) 0.0743(11) Uani 0.528(13) 1 d D U P B 1
C47B C 0.7302(11) 0.6911(18) 0.4837(8) 0.041(2) Uani 0.373(13) 1 d D U P C 2
H47B H 0.746072 0.776136 0.482438 0.049 Uiso 0.373(13) 1 calc R U P C 2
Cl1B Cl 0.7320(8) 0.6518(8) 0.5954(5) 0.0751(19) Uani 0.373(13) 1 d D U P C 2
Cl2B Cl 0.8479(9) 0.6688(8) 0.4191(5) 0.0638(16) Uani 0.373(13) 1 d D U P C 2
Cl3B Cl 0.5803(4) 0.6141(10) 0.4377(7) 0.093(2) Uani 0.373(13) 1 d D U P C 2
C47C C 0.744(2) 0.742(3) 0.4751(18) 0.045(5) Uani 0.047(2) 1 d D U P D 3
H47C H 0.726687 0.810972 0.495393 0.054 Uiso 0.047(2) 1 calc R U P D 3
Cl1C Cl 0.730(4) 0.652(4) 0.5674(16) 0.088(6) Uani 0.047(2) 1 d D U P D 3
Cl2C Cl 0.904(2) 0.791(3) 0.442(2) 0.110(6) Uani 0.047(2) 1 d D U P D 3
Cl3C Cl 0.6308(17) 0.6664(17) 0.3949(11) 0.084(5) Uani 0.047(2) 1 d D U P D 3
C47D C 0.749(3) 0.710(3) 0.480(2) 0.042(4) Uani 0.047(2) 1 d D U P E 4
H47D H 0.722279 0.765233 0.444496 0.051 Uiso 0.047(2) 1 calc R U P E 4
Cl1D Cl 0.688(3) 0.706(3) 0.5876(17) 0.114(6) Uani 0.047(2) 1 d D U P E 4
Cl2D Cl 0.916(2) 0.767(2) 0.4837(17) 0.092(5) Uani 0.047(2) 1 d D U P E 4
Cl3D Cl 0.688(2) 0.576(2) 0.4255(13) 0.085(5) Uani 0.047(2) 1 d D U P E 4


_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 C4 1.3713(19) . ?
N1 C1 1.3733(19) . ?
N1 H1N 0.879(16) . ?
N2 N2 1.291(3) 2_765 ?
N2 C1 1.3717(19) . ?
N3 C27 1.371(2) . ?
N3 C24 1.377(2) . ?
N3 H3N 0.915(17) . ?
N4 N4 1.288(3) 2 ?
N4 C24 1.371(2) . ?
C1 C2 1.396(2) . ?
C2 C3 1.412(2) . ?
C2 C5 1.479(2) . ?
C3 C4 1.387(2) . ?
C3 H3 0.9500 . ?
C4 C14 1.467(2) . ?
C5 C6 1.402(2) . ?
C5 C10 1.403(2) . ?
C6 C7 1.391(3) . ?
C6 C11 1.512(3) . ?
C7 C8 1.388(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.385(3) . ?
C8 C12 1.509(3) . ?
C9 C10 1.391(3) . ?
C9 H9 0.9500 . ?
C10 C13 1.507(3) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
C14 C15 1.379(2) . ?
C14 C23 1.436(2) . ?
C15 C16 1.409(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.370(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.414(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.418(2) . ?
C18 C23 1.428(2) . ?
C19 C20 1.362(3) . ?
C19 H19 0.9500 . ?
C20 C21 1.409(3) . ?
C20 H20 0.9500 . ?
C21 C22 1.374(2) . ?
C21 H21 0.9500 . ?
C22 C23 1.420(2) . ?
C22 H22 0.9500 . ?
C24 C25 1.394(2) . ?
C25 C26 1.413(2) . ?
C25 C28A 1.476(4) . ?
C25 C28B 1.50(3) . ?
C26 C27 1.386(3) . ?
C26 H26 0.9500 . ?
C27 C37 1.471(2) . ?
C28A C29A 1.405(3) . ?
C28A C33A 1.408(3) . ?
C29A C30A 1.393(3) . ?
C29A C34A 1.512(4) . ?
C30A C31A 1.392(4) . ?
C30A H30A 0.9500 . ?
C31A C32A 1.391(4) . ?
C31A C35A 1.521(3) . ?
C32A C33A 1.409(4) . ?
C32A H32A 0.9500 . ?
C33A C36A 1.494(4) . ?
C34A H34A 0.9800 . ?
C34A H34B 0.9800 . ?
C34A H34C 0.9800 . ?
C35A H35A 0.9800 . ?
C35A H35B 0.9800 . ?
C35A H35C 0.9800 . ?
C36A H36A 0.9800 . ?
C36A H36B 0.9800 . ?
C36A H36C 0.9800 . ?
C28B C29B 1.414(17) . ?
C28B C33B 1.415(17) . ?
C29B C30B 1.364(15) . ?
C29B C34B 1.527(17) . ?
C30B C31B 1.389(16) . ?
C30B H30B 0.9500 . ?
C31B C32B 1.395(16) . ?
C31B C35B 1.499(16) . ?
C32B C33B 1.409(17) . ?
C32B H32B 0.9500 . ?
C33B C36B 1.479(17) . ?
C34B H34D 0.9800 . ?
C34B H34E 0.9800 . ?
C34B H34F 0.9800 . ?
C35B H35D 0.9800 . ?
C35B H35E 0.9800 . ?
C35B H35F 0.9800 . ?
C36B H36D 0.9800 . ?
C36B H36E 0.9800 . ?
C36B H36F 0.9800 . ?
C37 C38 1.386(3) . ?
C37 C46 1.439(3) . ?
C38 C39 1.413(3) . ?
C38 H38 0.9500 . ?
C39 C40 1.368(3) . ?
C39 H39 0.9500 . ?
C40 C41 1.420(3) . ?
C40 H40 0.9500 . ?
C41 C42 1.421(3) . ?
C41 C46 1.434(2) . ?
C42 C43 1.365(4) . ?
C42 H42 0.9500 . ?
C43 C44 1.406(3) . ?
C43 H43 0.9500 . ?
C44 C45 1.373(3) . ?
C44 H44 0.9500 . ?
C45 C46 1.407(3) . ?
C45 H45 0.9500 . ?
C47A Cl3A 1.731(9) . ?
C47A Cl1A 1.749(8) . ?
C47A Cl2A 1.755(8) . ?
C47A H47A 1.0000 . ?
C47B Cl3B 1.732(12) . ?
C47B Cl1B 1.745(12) . ?
C47B Cl2B 1.756(12) . ?
C47B H47B 1.0000 . ?
C47C Cl3C 1.730(17) . ?
C47C Cl1C 1.746(17) . ?
C47C Cl2C 1.752(17) . ?
C47C H47C 1.0000 . ?
C47D Cl3D 1.727(18) . ?
C47D Cl1D 1.744(17) . ?
C47D Cl2D 1.750(18) . ?
C47D H47D 1.0000 . ?

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
C4 N1 C1 109.85(13) . . ?
C4 N1 H1N 127.6(16) . . ?
C1 N1 H1N 121.5(16) . . ?
N2 N2 C1 113.38(16) 2_765 . ?
C27 N3 C24 109.49(15) . . ?
C27 N3 H3N 124.6(17) . . ?
C24 N3 H3N 125.7(17) . . ?
N4 N4 C24 113.14(18) 2 . ?
N2 C1 N1 125.19(14) . . ?
N2 C1 C2 126.70(14) . . ?
N1 C1 C2 108.10(13) . . ?
C1 C2 C3 106.28(13) . . ?
C1 C2 C5 127.40(13) . . ?
C3 C2 C5 126.29(14) . . ?
C4 C3 C2 108.62(14) . . ?
C4 C3 H3 125.7 . . ?
C2 C3 H3 125.7 . . ?
N1 C4 C3 107.13(13) . . ?
N1 C4 C14 121.04(14) . . ?
C3 C4 C14 131.71(14) . . ?
C6 C5 C10 119.78(16) . . ?
C6 C5 C2 120.51(15) . . ?
C10 C5 C2 119.66(15) . . ?
C7 C6 C5 119.33(18) . . ?
C7 C6 C11 119.07(18) . . ?
C5 C6 C11 121.57(16) . . ?
C8 C7 C6 121.51(19) . . ?
C8 C7 H7 119.2 . . ?
C6 C7 H7 119.2 . . ?
C9 C8 C7 118.40(18) . . ?
C9 C8 C12 120.8(2) . . ?
C7 C8 C12 120.8(2) . . ?
C8 C9 C10 121.9(2) . . ?
C8 C9 H9 119.1 . . ?
C10 C9 H9 119.1 . . ?
C9 C10 C5 119.05(18) . . ?
C9 C10 C13 120.17(18) . . ?
C5 C10 C13 120.76(16) . . ?
C6 C11 H11A 109.5 . . ?
C6 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C6 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C8 C12 H12A 109.5 . . ?
C8 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C8 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C10 C13 H13A 109.5 . . ?
C10 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C10 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C15 C14 C23 119.10(14) . . ?
C15 C14 C4 119.04(14) . . ?
C23 C14 C4 121.82(14) . . ?
C14 C15 C16 121.97(16) . . ?
C14 C15 H15 119.0 . . ?
C16 C15 H15 119.0 . . ?
C17 C16 C15 119.83(17) . . ?
C17 C16 H16 120.1 . . ?
C15 C16 H16 120.1 . . ?
C16 C17 C18 120.58(15) . . ?
C16 C17 H17 119.7 . . ?
C18 C17 H17 119.7 . . ?
C17 C18 C19 120.86(15) . . ?
C17 C18 C23 119.91(15) . . ?
C19 C18 C23 119.23(16) . . ?
C20 C19 C18 121.26(16) . . ?
C20 C19 H19 119.4 . . ?
C18 C19 H19 119.4 . . ?
C19 C20 C21 119.66(17) . . ?
C19 C20 H20 120.2 . . ?
C21 C20 H20 120.2 . . ?
C22 C21 C20 120.99(18) . . ?
C22 C21 H21 119.5 . . ?
C20 C21 H21 119.5 . . ?
C21 C22 C23 120.68(16) . . ?
C21 C22 H22 119.7 . . ?
C23 C22 H22 119.7 . . ?
C22 C23 C18 118.09(15) . . ?
C22 C23 C14 123.34(14) . . ?
C18 C23 C14 118.56(15) . . ?
N4 C24 N3 125.00(16) . . ?
N4 C24 C25 126.58(16) . . ?
N3 C24 C25 108.41(15) . . ?
C24 C25 C26 106.05(15) . . ?
C24 C25 C28A 124.7(2) . . ?
C26 C25 C28A 129.2(2) . . ?
C24 C25 C28B 127.4(12) . . ?
C26 C25 C28B 126.5(12) . . ?
C27 C26 C25 108.72(16) . . ?
C27 C26 H26 125.6 . . ?
C25 C26 H26 125.6 . . ?
N3 C27 C26 107.31(15) . . ?
N3 C27 C37 120.46(16) . . ?
C26 C27 C37 132.18(16) . . ?
C29A C28A C33A 119.8(3) . . ?
C29A C28A C25 121.3(3) . . ?
C33A C28A C25 118.8(3) . . ?
C30A C29A C28A 119.1(2) . . ?
C30A C29A C34A 119.1(2) . . ?
C28A C29A C34A 121.7(2) . . ?
C31A C30A C29A 122.3(2) . . ?
C31A C30A H30A 118.8 . . ?
C29A C30A H30A 118.8 . . ?
C32A C31A C30A 118.1(2) . . ?
C32A C31A C35A 121.6(3) . . ?
C30A C31A C35A 120.3(3) . . ?
C31A C32A C33A 121.5(3) . . ?
C31A C32A H32A 119.3 . . ?
C33A C32A H32A 119.3 . . ?
C28A C33A C32A 119.1(3) . . ?
C28A C33A C36A 121.8(3) . . ?
C32A C33A C36A 118.9(3) . . ?
C29A C34A H34A 109.5 . . ?
C29A C34A H34B 109.5 . . ?
H34A C34A H34B 109.5 . . ?
C29A C34A H34C 109.5 . . ?
H34A C34A H34C 109.5 . . ?
H34B C34A H34C 109.5 . . ?
C31A C35A H35A 109.5 . . ?
C31A C35A H35B 109.5 . . ?
H35A C35A H35B 109.5 . . ?
C31A C35A H35C 109.5 . . ?
H35A C35A H35C 109.5 . . ?
H35B C35A H35C 109.5 . . ?
C33A C36A H36A 109.5 . . ?
C33A C36A H36B 109.5 . . ?
H36A C36A H36B 109.5 . . ?
C33A C36A H36C 109.5 . . ?
H36A C36A H36C 109.5 . . ?
H36B C36A H36C 109.5 . . ?
C29B C28B C33B 119.4(19) . . ?
C29B C28B C25 116.0(18) . . ?
C33B C28B C25 124.5(17) . . ?
C30B C29B C28B 114.3(16) . . ?
C30B C29B C34B 126.9(19) . . ?
C28B C29B C34B 118.6(18) . . ?
C29B C30B C31B 130.9(16) . . ?
C29B C30B H30B 114.5 . . ?
C31B C30B H30B 114.5 . . ?
C30B C31B C32B 112.7(15) . . ?
C30B C31B C35B 123.9(17) . . ?
C32B C31B C35B 122.9(18) . . ?
C31B C32B C33B 121.5(17) . . ?
C31B C32B H32B 119.3 . . ?
C33B C32B H32B 119.3 . . ?
C32B C33B C28B 121.0(18) . . ?
C32B C33B C36B 118(2) . . ?
C28B C33B C36B 121(2) . . ?
C29B C34B H34D 109.5 . . ?
C29B C34B H34E 109.5 . . ?
H34D C34B H34E 109.5 . . ?
C29B C34B H34F 109.5 . . ?
H34D C34B H34F 109.5 . . ?
H34E C34B H34F 109.5 . . ?
C31B C35B H35D 109.5 . . ?
C31B C35B H35E 109.5 . . ?
H35D C35B H35E 109.5 . . ?
C31B C35B H35F 109.5 . . ?
H35D C35B H35F 109.5 . . ?
H35E C35B H35F 109.5 . . ?
C33B C36B H36D 109.5 . . ?
C33B C36B H36E 109.5 . . ?
H36D C36B H36E 109.5 . . ?
C33B C36B H36F 109.5 . . ?
H36D C36B H36F 109.5 . . ?
H36E C36B H36F 109.5 . . ?
C38 C37 C46 119.86(16) . . ?
C38 C37 C27 118.43(17) . . ?
C46 C37 C27 121.69(17) . . ?
C37 C38 C39 121.09(19) . . ?
C37 C38 H38 119.5 . . ?
C39 C38 H38 119.5 . . ?
C40 C39 C38 120.5(2) . . ?
C40 C39 H39 119.7 . . ?
C38 C39 H39 119.7 . . ?
C39 C40 C41 120.32(19) . . ?
C39 C40 H40 119.8 . . ?
C41 C40 H40 119.8 . . ?
C40 C41 C42 120.96(19) . . ?
C40 C41 C46 120.18(18) . . ?
C42 C41 C46 118.9(2) . . ?
C43 C42 C41 121.3(2) . . ?
C43 C42 H42 119.4 . . ?
C41 C42 H42 119.4 . . ?
C42 C43 C44 119.6(2) . . ?
C42 C43 H43 120.2 . . ?
C44 C43 H43 120.2 . . ?
C45 C44 C43 120.8(2) . . ?
C45 C44 H44 119.6 . . ?
C43 C44 H44 119.6 . . ?
C44 C45 C46 121.2(2) . . ?
C44 C45 H45 119.4 . . ?
C46 C45 H45 119.4 . . ?
C45 C46 C41 118.15(18) . . ?
C45 C46 C37 123.89(16) . . ?
C41 C46 C37 117.94(18) . . ?
Cl3A C47A Cl1A 113.5(6) . . ?
Cl3A C47A Cl2A 110.6(6) . . ?
Cl1A C47A Cl2A 110.3(6) . . ?
Cl3A C47A H47A 107.4 . . ?
Cl1A C47A H47A 107.4 . . ?
Cl2A C47A H47A 107.4 . . ?
Cl3B C47B Cl1B 109.2(8) . . ?
Cl3B C47B Cl2B 110.2(8) . . ?
Cl1B C47B Cl2B 113.3(10) . . ?
Cl3B C47B H47B 108.0 . . ?
Cl1B C47B H47B 108.0 . . ?
Cl2B C47B H47B 108.0 . . ?
Cl3C C47C Cl1C 109.4(17) . . ?
Cl3C C47C Cl2C 116.2(19) . . ?
Cl1C C47C Cl2C 106.7(18) . . ?
Cl3C C47C H47C 108.1 . . ?
Cl1C C47C H47C 108.1 . . ?
Cl2C C47C H47C 108.1 . . ?
Cl3D C47D Cl1D 112.9(19) . . ?
Cl3D C47D Cl2D 111.3(19) . . ?
Cl1D C47D Cl2D 110.4(19) . . ?
Cl3D C47D H47D 107.3 . . ?
Cl1D C47D H47D 107.3 . . ?
Cl2D C47D H47D 107.3 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N2 N2 C1 N1 -0.8(3) 2_765 . . . ?
N2 N2 C1 C2 178.65(18) 2_765 . . . ?
C4 N1 C1 N2 -179.24(15) . . . . ?
C4 N1 C1 C2 1.24(19) . . . . ?
N2 C1 C2 C3 179.68(16) . . . . ?
N1 C1 C2 C3 -0.81(18) . . . . ?
N2 C1 C2 C5 1.6(3) . . . . ?
N1 C1 C2 C5 -178.86(16) . . . . ?
C1 C2 C3 C4 0.10(19) . . . . ?
C5 C2 C3 C4 178.18(16) . . . . ?
C1 N1 C4 C3 -1.16(19) . . . . ?
C1 N1 C4 C14 -177.66(14) . . . . ?
C2 C3 C4 N1 0.64(19) . . . . ?
C2 C3 C4 C14 176.62(17) . . . . ?
C1 C2 C5 C6 -112.9(2) . . . . ?
C3 C2 C5 C6 69.4(2) . . . . ?
C1 C2 C5 C10 69.6(2) . . . . ?
C3 C2 C5 C10 -108.1(2) . . . . ?
C10 C5 C6 C7 -0.8(3) . . . . ?
C2 C5 C6 C7 -178.27(16) . . . . ?
C10 C5 C6 C11 -178.98(18) . . . . ?
C2 C5 C6 C11 3.5(3) . . . . ?
C5 C6 C7 C8 -1.5(3) . . . . ?
C11 C6 C7 C8 176.8(2) . . . . ?
C6 C7 C8 C9 2.5(3) . . . . ?
C6 C7 C8 C12 -176.7(2) . . . . ?
C7 C8 C9 C10 -1.2(3) . . . . ?
C12 C8 C9 C10 178.0(2) . . . . ?
C8 C9 C10 C5 -1.0(3) . . . . ?
C8 C9 C10 C13 177.43(19) . . . . ?
C6 C5 C10 C9 2.0(2) . . . . ?
C2 C5 C10 C9 179.48(15) . . . . ?
C6 C5 C10 C13 -176.41(17) . . . . ?
C2 C5 C10 C13 1.1(2) . . . . ?
N1 C4 C14 C15 35.5(2) . . . . ?
C3 C4 C14 C15 -140.02(19) . . . . ?
N1 C4 C14 C23 -146.86(16) . . . . ?
C3 C4 C14 C23 37.6(3) . . . . ?
C23 C14 C15 C16 -0.9(3) . . . . ?
C4 C14 C15 C16 176.80(16) . . . . ?
C14 C15 C16 C17 -0.3(3) . . . . ?
C15 C16 C17 C18 0.3(3) . . . . ?
C16 C17 C18 C19 -178.44(18) . . . . ?
C16 C17 C18 C23 1.0(3) . . . . ?
C17 C18 C19 C20 -178.53(18) . . . . ?
C23 C18 C19 C20 2.1(3) . . . . ?
C18 C19 C20 C21 0.4(3) . . . . ?
C19 C20 C21 C22 -1.2(3) . . . . ?
C20 C21 C22 C23 -0.5(3) . . . . ?
C21 C22 C23 C18 2.9(3) . . . . ?
C21 C22 C23 C14 -178.04(17) . . . . ?
C17 C18 C23 C22 176.94(16) . . . . ?
C19 C18 C23 C22 -3.6(2) . . . . ?
C17 C18 C23 C14 -2.2(2) . . . . ?
C19 C18 C23 C14 177.26(15) . . . . ?
C15 C14 C23 C22 -176.92(17) . . . . ?
C4 C14 C23 C22 5.4(2) . . . . ?
C15 C14 C23 C18 2.1(2) . . . . ?
C4 C14 C23 C18 -175.52(15) . . . . ?
N4 N4 C24 N3 -1.6(3) 2 . . . ?
N4 N4 C24 C25 179.9(2) 2 . . . ?
C27 N3 C24 N4 -177.27(17) . . . . ?
C27 N3 C24 C25 1.4(2) . . . . ?
N4 C24 C25 C26 177.89(18) . . . . ?
N3 C24 C25 C26 -0.8(2) . . . . ?
N4 C24 C25 C28A 0.0(3) . . . . ?
N3 C24 C25 C28A -178.7(2) . . . . ?
N4 C24 C25 C28B -3.4(12) . . . . ?
N3 C24 C25 C28B 177.9(12) . . . . ?
C24 C25 C26 C27 -0.1(2) . . . . ?
C28A C25 C26 C27 177.7(2) . . . . ?
C28B C25 C26 C27 -178.9(12) . . . . ?
C24 N3 C27 C26 -1.5(2) . . . . ?
C24 N3 C27 C37 -179.15(16) . . . . ?
C25 C26 C27 N3 1.0(2) . . . . ?
C25 C26 C27 C37 178.26(19) . . . . ?
C24 C25 C28A C29A -62.4(4) . . . . ?
C26 C25 C28A C29A 120.2(3) . . . . ?
C24 C25 C28A C33A 114.2(3) . . . . ?
C26 C25 C28A C33A -63.2(4) . . . . ?
C33A C28A C29A C30A -0.3(5) . . . . ?
C25 C28A C29A C30A 176.3(3) . . . . ?
C33A C28A C29A C34A 179.9(3) . . . . ?
C25 C28A C29A C34A -3.6(5) . . . . ?
C28A C29A C30A C31A -1.1(4) . . . . ?
C34A C29A C30A C31A 178.8(3) . . . . ?
C29A C30A C31A C32A 2.9(4) . . . . ?
C29A C30A C31A C35A -174.6(3) . . . . ?
C30A C31A C32A C33A -3.4(5) . . . . ?
C35A C31A C32A C33A 174.1(4) . . . . ?
C29A C28A C33A C32A -0.3(6) . . . . ?
C25 C28A C33A C32A -176.9(4) . . . . ?
C29A C28A C33A C36A 175.4(4) . . . . ?
C25 C28A C33A C36A -1.3(6) . . . . ?
C31A C32A C33A C28A 2.2(6) . . . . ?
C31A C32A C33A C36A -173.6(4) . . . . ?
C24 C25 C28B C29B -71(2) . . . . ?
C26 C25 C28B C29B 107.3(16) . . . . ?
C24 C25 C28B C33B 113(3) . . . . ?
C26 C25 C28B C33B -69(3) . . . . ?
C33B C28B C29B C30B -1(2) . . . . ?
C25 C28B C29B C30B -177(2) . . . . ?
C33B C28B C29B C34B -176(3) . . . . ?
C25 C28B C29B C34B 8(2) . . . . ?
C28B C29B C30B C31B -2.3(16) . . . . ?
C34B C29B C30B C31B 172(2) . . . . ?
C29B C30B C31B C32B 5(3) . . . . ?
C29B C30B C31B C35B -168.3(16) . . . . ?
C30B C31B C32B C33B -4(4) . . . . ?
C35B C31B C32B C33B 169(3) . . . . ?
C31B C32B C33B C28B 2(5) . . . . ?
C31B C32B C33B C36B -178(3) . . . . ?
C29B C28B C33B C32B 1(5) . . . . ?
C25 C28B C33B C32B 177(3) . . . . ?
C29B C28B C33B C36B -180(3) . . . . ?
C25 C28B C33B C36B -4(6) . . . . ?
N3 C27 C37 C38 36.7(3) . . . . ?
C26 C27 C37 C38 -140.3(2) . . . . ?
N3 C27 C37 C46 -142.14(18) . . . . ?
C26 C27 C37 C46 40.9(3) . . . . ?
C46 C37 C38 C39 -2.0(3) . . . . ?
C27 C37 C38 C39 179.2(2) . . . . ?
C37 C38 C39 C40 -0.7(4) . . . . ?
C38 C39 C40 C41 1.8(4) . . . . ?
C39 C40 C41 C42 178.9(2) . . . . ?
C39 C40 C41 C46 -0.3(4) . . . . ?
C40 C41 C42 C43 -176.7(2) . . . . ?
C46 C41 C42 C43 2.5(3) . . . . ?
C41 C42 C43 C44 0.0(4) . . . . ?
C42 C43 C44 C45 -1.7(4) . . . . ?
C43 C44 C45 C46 0.7(4) . . . . ?
C44 C45 C46 C41 1.8(3) . . . . ?
C44 C45 C46 C37 179.8(2) . . . . ?
C40 C41 C46 C45 175.8(2) . . . . ?
C42 C41 C46 C45 -3.4(3) . . . . ?
C40 C41 C46 C37 -2.3(3) . . . . ?
C42 C41 C46 C37 178.49(19) . . . . ?
C38 C37 C46 C45 -174.6(2) . . . . ?
C27 C37 C46 C45 4.2(3) . . . . ?
C38 C37 C46 C41 3.4(3) . . . . ?
C27 C37 C46 C41 -177.75(17) . . . . ?

_refine_diff_density_max         1.122
_refine_diff_density_min         -0.482
_refine_diff_density_rms         0.074

####################################################################### 
# 
# 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_RD018
_database_code_depnum_ccdc_archive 'CCDC 2449927'
loop_
_audit_author_name
_audit_author_address
'Katherine Robertson'
;Saint Marys University
Canada
;
_audit_update_record             
;
2025-05-09 deposited with the CCDC.	2025-07-29 downloaded from the CCDC.
;

#============================================================================== 

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C19 H18 N2), 0.78(H2 O), 0.22(C H4 O)'
_chemical_formula_sum            'C19.11 H19.22 N2 O0.50'
_chemical_formula_weight         284.92

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      trigonal
_space_group_IT_number           148
_space_group_name_H-M_alt        'R -3 :H'
_space_group_name_Hall           '-R 3'

_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'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'

_cell_length_a                   32.517(8)
_cell_length_b                   32.517(8)
_cell_length_c                   8.260(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     7564(4)
_cell_formula_units_Z            18
_cell_measurement_temperature    125(2)
_cell_measurement_reflns_used    6417
_cell_measurement_theta_min      2.17
_cell_measurement_theta_max      25.10

_exptl_crystal_description       rod
_exptl_crystal_colour            red
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.126
_exptl_crystal_F_000             2734
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.950
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.068
_shelx_estimated_absorpt_T_min   0.938
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6568
_exptl_absorpt_correction_T_max  0.7452
_exptl_absorpt_process_details   'SADABS; Bruker 2009'
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      125(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?

_diffrn_reflns_number            25280
_diffrn_reflns_av_unetI/netI     0.0419
_diffrn_reflns_av_R_equivalents  0.0681
_diffrn_reflns_limit_h_min       -39
_diffrn_reflns_limit_h_max       39
_diffrn_reflns_limit_k_min       -39
_diffrn_reflns_limit_k_max       39
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         1.252
_diffrn_reflns_theta_max         25.405
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3086
_reflns_number_gt                2208
_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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          
;
 Refined as a 2-component twin.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+20.5315P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_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         3086
_refine_ls_number_parameters     307
_refine_ls_number_restraints     478
_refine_ls_R_factor_all          0.1015
_refine_ls_R_factor_gt           0.0685
_refine_ls_wR_factor_ref         0.1236
_refine_ls_wR_factor_gt          0.1127
_refine_ls_goodness_of_fit_ref   1.156
_refine_ls_restrained_S_all      1.089
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1A O 0.45579(17) 0.57771(18) 0.4486(5) 0.0602(12) Uani 0.5 1 d D . P . .
H1OA H 0.451(3) 0.5537(18) 0.503(8) 0.090 Uiso 0.5 1 d D U P . .
H1OB H 0.440(3) 0.582(4) 0.522(9) 0.090 Uiso 0.390(3) 1 d D U P A 1
C20 C 0.4156(10) 0.5822(12) 0.402(4) 0.062(8) Uani 0.110(3) 1 d . . P B 2
H20A H 0.412679 0.604234 0.475863 0.093 Uiso 0.110(3) 1 calc R U P B 2
H20B H 0.386682 0.551072 0.407447 0.093 Uiso 0.110(3) 1 calc R U P B 2
H20C H 0.420082 0.594486 0.291216 0.093 Uiso 0.110(3) 1 calc R U P B 2
N1 N 0.45797(8) 0.42694(8) 0.6642(2) 0.0381(6) Uani 1 1 d . . . . .
H1N H 0.4774(11) 0.4211(10) 0.613(4) 0.055(10) Uiso 1 1 d . . . . .
N2 N 0.48621(8) 0.50476(8) 0.5435(2) 0.0372(5) Uani 1 1 d . . . . .
C1 C 0.45812(9) 0.46902(9) 0.6475(3) 0.0370(6) Uani 1 1 d . . . . .
C2 C 0.42373(9) 0.46784(10) 0.7513(3) 0.0372(6) Uani 1 1 d D . . . .
C3 C 0.40318(10) 0.42387(10) 0.8288(3) 0.0409(7) Uani 1 1 d . . . . .
H3 H 0.378404 0.412992 0.906634 0.049 Uiso 1 1 calc R U . . .
C4 C 0.42428(10) 0.39842(10) 0.7753(3) 0.0397(7) Uani 1 1 d . . . . .
C5A C 0.4175(5) 0.5099(4) 0.781(2) 0.033(2) Uani 0.5 1 d D U P C 1
C6A C 0.3740(4) 0.5049(3) 0.730(2) 0.037(2) Uani 0.5 1 d D U P C 1
C7A C 0.3643(3) 0.5415(3) 0.7605(18) 0.050(2) Uani 0.5 1 d D U P C 1
H7A H 0.334938 0.537933 0.724312 0.060 Uiso 0.5 1 calc R U P C 1
C8A C 0.3956(3) 0.5826(3) 0.8406(15) 0.044(2) Uani 0.5 1 d D U P C 1
C9A C 0.4384(3) 0.5871(3) 0.8915(17) 0.041(2) Uani 0.5 1 d D U P C 1
H9A H 0.460497 0.615011 0.947769 0.050 Uiso 0.5 1 calc R U P C 1
C10A C 0.4498(4) 0.5515(4) 0.861(2) 0.032(2) Uani 0.5 1 d D U P C 1
C11A C 0.3364(6) 0.4599(5) 0.647(3) 0.047(3) Uani 0.5 1 d D U P C 1
H11A H 0.306208 0.459666 0.645135 0.071 Uiso 0.5 1 calc R U P C 1
H11B H 0.332455 0.432018 0.706516 0.071 Uiso 0.5 1 calc R U P C 1
H11C H 0.346500 0.458953 0.535938 0.071 Uiso 0.5 1 calc R U P C 1
C12A C 0.3835(5) 0.6214(4) 0.873(3) 0.084(4) Uani 0.5 1 d D U P C 1
H12A H 0.409862 0.647682 0.930514 0.126 Uiso 0.25 1 calc R U P C 1
H12B H 0.378278 0.632937 0.769506 0.126 Uiso 0.25 1 calc R U P C 1
H12C H 0.354664 0.608562 0.938638 0.126 Uiso 0.25 1 calc R U P C 1
H12D H 0.352008 0.611772 0.828591 0.126 Uiso 0.25 1 calc R U P C 1
H12E H 0.383591 0.626517 0.989599 0.126 Uiso 0.25 1 calc R U P C 1
H12F H 0.407206 0.650892 0.820468 0.126 Uiso 0.25 1 calc R U P C 1
C13A C 0.4961(6) 0.5578(8) 0.922(3) 0.046(3) Uani 0.5 1 d D U P C 1
H13A H 0.490137 0.536333 1.013600 0.068 Uiso 0.5 1 calc R U P C 1
H13B H 0.516495 0.590697 0.957259 0.068 Uiso 0.5 1 calc R U P C 1
H13C H 0.511827 0.550403 0.834979 0.068 Uiso 0.5 1 calc R U P C 1
C5B C 0.4065(4) 0.5022(4) 0.771(3) 0.033(2) Uani 0.5 1 d D U P C 2
C6B C 0.3611(4) 0.4919(4) 0.726(2) 0.045(3) Uani 0.5 1 d D U P C 2
C7B C 0.3488(3) 0.5261(4) 0.7594(18) 0.056(3) Uani 0.5 1 d D U P C 2
H7B H 0.318261 0.520089 0.727640 0.067 Uiso 0.5 1 calc R U P C 2
C8B C 0.3787(3) 0.5684(4) 0.8367(18) 0.055(3) Uani 0.5 1 d D U P C 2
C9B C 0.4233(3) 0.5772(4) 0.8813(18) 0.047(2) Uani 0.5 1 d D U P C 2
H9B H 0.444721 0.606522 0.931756 0.056 Uiso 0.5 1 calc R U P C 2
C10B C 0.4374(4) 0.5436(5) 0.853(3) 0.039(3) Uani 0.5 1 d D U P C 2
C11B C 0.3262(7) 0.4452(5) 0.647(3) 0.067(4) Uani 0.5 1 d D U P C 2
H11D H 0.314346 0.419832 0.727979 0.101 Uiso 0.5 1 calc R U P C 2
H11E H 0.342181 0.438068 0.559929 0.101 Uiso 0.5 1 calc R U P C 2
H11F H 0.299596 0.447571 0.601892 0.101 Uiso 0.5 1 calc R U P C 2
C12B C 0.3649(5) 0.6056(5) 0.875(3) 0.095(5) Uani 0.5 1 d D U P C 2
H12G H 0.332501 0.594589 0.837223 0.142 Uiso 0.25 1 calc R U P C 2
H12H H 0.366354 0.610631 0.992794 0.142 Uiso 0.25 1 calc R U P C 2
H12I H 0.386904 0.635442 0.821470 0.142 Uiso 0.25 1 calc R U P C 2
H12J H 0.391338 0.632518 0.930435 0.142 Uiso 0.25 1 calc R U P C 2
H12K H 0.357485 0.616477 0.774864 0.142 Uiso 0.25 1 calc R U P C 2
H12L H 0.336936 0.591666 0.946188 0.142 Uiso 0.25 1 calc R U P C 2
C13B C 0.4847(5) 0.5525(7) 0.915(3) 0.037(3) Uani 0.5 1 d D U P C 2
H13D H 0.498387 0.580203 0.986732 0.056 Uiso 0.5 1 calc R U P C 2
H13E H 0.506109 0.558422 0.823475 0.056 Uiso 0.5 1 calc R U P C 2
H13F H 0.480287 0.524594 0.975147 0.056 Uiso 0.5 1 calc R U P C 2
C14 C 0.41667(10) 0.35236(10) 0.8237(3) 0.0400(7) Uani 1 1 d . . . . .
C15 C 0.37522(11) 0.32066(10) 0.9063(3) 0.0457(7) Uani 1 1 d . . . . .
H15 H 0.352090 0.329437 0.930729 0.055 Uiso 1 1 calc R U . . .
C16 C 0.36782(12) 0.27676(11) 0.9524(3) 0.0541(8) Uani 1 1 d . . . . .
H16 H 0.339523 0.255563 1.008510 0.065 Uiso 1 1 calc R U . . .
C17 C 0.40066(13) 0.26304(12) 0.9186(3) 0.0596(9) Uani 1 1 d . . . . .
H17 H 0.394993 0.232508 0.949700 0.072 Uiso 1 1 calc R U . . .
C18 C 0.44220(12) 0.29446(11) 0.8384(3) 0.0538(8) Uani 1 1 d . . . . .
H18 H 0.465343 0.285564 0.815869 0.065 Uiso 1 1 calc R U . . .
C19 C 0.45007(11) 0.33835(10) 0.7913(3) 0.0465(7) Uani 1 1 d . . . . .
H19 H 0.478587 0.359442 0.736096 0.056 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
O1A C20 1.44(3) . ?
O1A H1OA 0.85(2) . ?
O1A H1OB 0.84(2) . ?
C20 H20A 0.9800 . ?
C20 H20B 0.9800 . ?
C20 H20C 0.9800 . ?
N1 C1 1.373(4) . ?
N1 C4 1.373(3) . ?
N1 H1N 0.86(3) . ?
N2 N2 1.301(4) 10_666 ?
N2 C1 1.364(3) . ?
C1 C2 1.394(4) . ?
C2 C3 1.395(4) . ?
C2 C5B 1.489(7) . ?
C2 C5A 1.500(7) . ?
C3 C4 1.385(4) . ?
C3 H3 0.9500 . ?
C4 C14 1.447(4) . ?
C5A C10A 1.396(9) . ?
C5A C6A 1.405(9) . ?
C6A C7A 1.399(9) . ?
C6A C11A 1.524(9) . ?
C7A C8A 1.377(9) . ?
C7A H7A 0.9500 . ?
C8A C9A 1.389(10) . ?
C8A C12A 1.521(10) . ?
C9A C10A 1.403(10) . ?
C9A H9A 0.9500 . ?
C10A C13A 1.500(10) . ?
C11A H11A 0.9800 . ?
C11A H11B 0.9800 . ?
C11A H11C 0.9800 . ?
C12A H12A 0.9800 . ?
C12A H12B 0.9800 . ?
C12A H12C 0.9800 . ?
C12A H12D 0.9800 . ?
C12A H12E 0.9800 . ?
C12A H12F 0.9800 . ?
C13A H13A 0.9800 . ?
C13A H13B 0.9800 . ?
C13A H13C 0.9800 . ?
C5B C10B 1.386(9) . ?
C5B C6B 1.393(9) . ?
C6B C7B 1.382(10) . ?
C6B C11B 1.515(9) . ?
C7B C8B 1.381(9) . ?
C7B H7B 0.9500 . ?
C8B C9B 1.381(9) . ?
C8B C12B 1.520(11) . ?
C9B C10B 1.400(10) . ?
C9B H9B 0.9500 . ?
C10B C13B 1.505(9) . ?
C11B H11D 0.9800 . ?
C11B H11E 0.9800 . ?
C11B H11F 0.9800 . ?
C12B H12G 0.9800 . ?
C12B H12H 0.9800 . ?
C12B H12I 0.9800 . ?
C12B H12J 0.9800 . ?
C12B H12K 0.9800 . ?
C12B H12L 0.9800 . ?
C13B H13D 0.9800 . ?
C13B H13E 0.9800 . ?
C13B H13F 0.9800 . ?
C14 C19 1.398(4) . ?
C14 C15 1.398(4) . ?
C15 C16 1.377(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.376(5) . ?
C16 H16 0.9500 . ?
C17 C18 1.388(4) . ?
C17 H17 0.9500 . ?
C18 C19 1.374(4) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C20 O1A H1OA 119(6) . . ?
H1OA O1A H1OB 86(8) . . ?
O1A C20 H20A 109.5 . . ?
O1A C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O1A C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C1 N1 C4 110.2(2) . . ?
C1 N1 H1N 122(2) . . ?
C4 N1 H1N 127(2) . . ?
N2 N2 C1 113.1(3) 10_666 . ?
N2 C1 N1 125.4(2) . . ?
N2 C1 C2 126.7(3) . . ?
N1 C1 C2 107.9(2) . . ?
C1 C2 C3 106.1(2) . . ?
C1 C2 C5B 130.2(8) . . ?
C3 C2 C5B 123.5(8) . . ?
C1 C2 C5A 123.2(8) . . ?
C3 C2 C5A 130.2(8) . . ?
C4 C3 C2 109.8(2) . . ?
C4 C3 H3 125.1 . . ?
C2 C3 H3 125.1 . . ?
N1 C4 C3 106.0(3) . . ?
N1 C4 C14 123.3(3) . . ?
C3 C4 C14 130.6(2) . . ?
C10A C5A C6A 118.7(7) . . ?
C10A C5A C2 125.6(8) . . ?
C6A C5A C2 115.6(8) . . ?
C7A C6A C5A 119.4(8) . . ?
C7A C6A C11A 119.0(9) . . ?
C5A C6A C11A 121.6(9) . . ?
C8A C7A C6A 122.5(8) . . ?
C8A C7A H7A 118.7 . . ?
C6A C7A H7A 118.7 . . ?
C7A C8A C9A 117.7(8) . . ?
C7A C8A C12A 121.0(10) . . ?
C9A C8A C12A 121.3(10) . . ?
C8A C9A C10A 121.5(8) . . ?
C8A C9A H9A 119.3 . . ?
C10A C9A H9A 119.3 . . ?
C5A C10A C9A 120.2(8) . . ?
C5A C10A C13A 120.5(10) . . ?
C9A C10A C13A 119.3(10) . . ?
C6A C11A H11A 109.5 . . ?
C6A C11A H11B 109.5 . . ?
H11A C11A H11B 109.5 . . ?
C6A C11A H11C 109.5 . . ?
H11A C11A H11C 109.5 . . ?
H11B C11A H11C 109.5 . . ?
C8A C12A H12A 109.5 . . ?
C8A C12A H12B 109.5 . . ?
H12A C12A H12B 109.5 . . ?
C8A C12A H12C 109.5 . . ?
H12A C12A H12C 109.5 . . ?
H12B C12A H12C 109.5 . . ?
H12D C12A H12E 109.5 . . ?
H12D C12A H12F 109.5 . . ?
H12E C12A H12F 109.5 . . ?
C10A C13A H13A 109.5 . . ?
C10A C13A H13B 109.5 . . ?
H13A C13A H13B 109.5 . . ?
C10A C13A H13C 109.5 . . ?
H13A C13A H13C 109.5 . . ?
H13B C13A H13C 109.5 . . ?
C10B C5B C6B 122.1(8) . . ?
C10B C5B C2 115.0(9) . . ?
C6B C5B C2 122.7(8) . . ?
C7B C6B C5B 116.7(8) . . ?
C7B C6B C11B 121.3(10) . . ?
C5B C6B C11B 122.0(10) . . ?
C8B C7B C6B 123.5(8) . . ?
C8B C7B H7B 118.3 . . ?
C6B C7B H7B 118.3 . . ?
C9B C8B C7B 118.2(8) . . ?
C9B C8B C12B 118.4(10) . . ?
C7B C8B C12B 123.4(9) . . ?
C8B C9B C10B 120.8(8) . . ?
C8B C9B H9B 119.6 . . ?
C10B C9B H9B 119.6 . . ?
C5B C10B C9B 118.6(9) . . ?
C5B C10B C13B 121.7(10) . . ?
C9B C10B C13B 119.7(10) . . ?
C6B C11B H11D 109.5 . . ?
C6B C11B H11E 109.5 . . ?
H11D C11B H11E 109.5 . . ?
C6B C11B H11F 109.5 . . ?
H11D C11B H11F 109.5 . . ?
H11E C11B H11F 109.5 . . ?
C8B C12B H12G 109.5 . . ?
C8B C12B H12H 109.5 . . ?
H12G C12B H12H 109.5 . . ?
C8B C12B H12I 109.5 . . ?
H12G C12B H12I 109.5 . . ?
H12H C12B H12I 109.5 . . ?
H12J C12B H12K 109.5 . . ?
H12J C12B H12L 109.5 . . ?
H12K C12B H12L 109.5 . . ?
C10B C13B H13D 109.5 . . ?
C10B C13B H13E 109.5 . . ?
H13D C13B H13E 109.5 . . ?
C10B C13B H13F 109.5 . . ?
H13D C13B H13F 109.5 . . ?
H13E C13B H13F 109.5 . . ?
C19 C14 C15 118.2(3) . . ?
C19 C14 C4 121.7(3) . . ?
C15 C14 C4 120.1(3) . . ?
C16 C15 C14 120.2(3) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C17 C16 C15 121.2(3) . . ?
C17 C16 H16 119.4 . . ?
C15 C16 H16 119.4 . . ?
C16 C17 C18 119.0(3) . . ?
C16 C17 H17 120.5 . . ?
C18 C17 H17 120.5 . . ?
C19 C18 C17 120.5(3) . . ?
C19 C18 H18 119.8 . . ?
C17 C18 H18 119.8 . . ?
C18 C19 C14 120.9(3) . . ?
C18 C19 H19 119.6 . . ?
C14 C19 H19 119.6 . . ?

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
N2 N2 C1 N1 0.6(4) 10_666 . . . ?
N2 N2 C1 C2 -177.3(3) 10_666 . . . ?
C4 N1 C1 N2 -177.9(2) . . . . ?
C4 N1 C1 C2 0.3(3) . . . . ?
N2 C1 C2 C3 177.9(2) . . . . ?
N1 C1 C2 C3 -0.4(3) . . . . ?
N2 C1 C2 C5B 3.7(8) . . . . ?
N1 C1 C2 C5B -174.5(7) . . . . ?
N2 C1 C2 C5A -9.4(8) . . . . ?
N1 C1 C2 C5A 172.4(7) . . . . ?
C1 C2 C3 C4 0.3(3) . . . . ?
C5B C2 C3 C4 174.9(7) . . . . ?
C5A C2 C3 C4 -171.8(7) . . . . ?
C1 N1 C4 C3 -0.2(3) . . . . ?
C1 N1 C4 C14 -177.7(2) . . . . ?
C2 C3 C4 N1 0.0(3) . . . . ?
C2 C3 C4 C14 177.3(3) . . . . ?
C1 C2 C5A C10A -67.7(19) . . . . ?
C3 C2 C5A C10A 103.2(16) . . . . ?
C1 C2 C5A C6A 116.0(12) . . . . ?
C3 C2 C5A C6A -73.1(16) . . . . ?
C10A C5A C6A C7A 0(2) . . . . ?
C2 C5A C6A C7A 177.0(13) . . . . ?
C10A C5A C6A C11A -178.0(17) . . . . ?
C2 C5A C6A C11A -1(2) . . . . ?
C5A C6A C7A C8A -0.9(19) . . . . ?
C11A C6A C7A C8A 177.5(14) . . . . ?
C6A C7A C8A C9A 0.4(16) . . . . ?
C6A C7A C8A C12A -179.3(15) . . . . ?
C7A C8A C9A C10A 0.5(17) . . . . ?
C12A C8A C9A C10A -179.7(15) . . . . ?
C6A C5A C10A C9A 1(2) . . . . ?
C2 C5A C10A C9A -175.7(16) . . . . ?
C6A C5A C10A C13A 178.2(18) . . . . ?
C2 C5A C10A C13A 2(3) . . . . ?
C8A C9A C10A C5A -1(2) . . . . ?
C8A C9A C10A C13A -178.7(16) . . . . ?
C1 C2 C5B C10B -74.8(17) . . . . ?
C3 C2 C5B C10B 111.9(13) . . . . ?
C1 C2 C5B C6B 111.0(15) . . . . ?
C3 C2 C5B C6B -62.2(19) . . . . ?
C10B C5B C6B C7B 3(2) . . . . ?
C2 C5B C6B C7B 176.5(15) . . . . ?
C10B C5B C6B C11B -175.7(19) . . . . ?
C2 C5B C6B C11B -2(3) . . . . ?
C5B C6B C7B C8B -1(2) . . . . ?
C11B C6B C7B C8B 177.4(16) . . . . ?
C6B C7B C8B C9B 0.7(19) . . . . ?
C6B C7B C8B C12B -179.2(17) . . . . ?
C7B C8B C9B C10B -2(2) . . . . ?
C12B C8B C9B C10B 178.1(17) . . . . ?
C6B C5B C10B C9B -4(3) . . . . ?
C2 C5B C10B C9B -178.1(16) . . . . ?
C6B C5B C10B C13B 174.5(19) . . . . ?
C2 C5B C10B C13B 0(2) . . . . ?
C8B C9B C10B C5B 3(2) . . . . ?
C8B C9B C10B C13B -175.0(17) . . . . ?
N1 C4 C14 C19 15.7(4) . . . . ?
C3 C4 C14 C19 -161.2(3) . . . . ?
N1 C4 C14 C15 -164.8(2) . . . . ?
C3 C4 C14 C15 18.3(4) . . . . ?
C19 C14 C15 C16 -0.6(4) . . . . ?
C4 C14 C15 C16 179.9(2) . . . . ?
C14 C15 C16 C17 -0.1(4) . . . . ?
C15 C16 C17 C18 0.8(4) . . . . ?
C16 C17 C18 C19 -0.9(4) . . . . ?
C17 C18 C19 C14 0.3(4) . . . . ?
C15 C14 C19 C18 0.5(4) . . . . ?
C4 C14 C19 C18 180.0(2) . . . . ?

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
N1 H1N O1A 0.86(3) 2.21(3) 3.030(5) 159(3) 10_666 yes

_refine_diff_density_max         0.181
_refine_diff_density_min         -0.204
_refine_diff_density_rms         0.036

####################################################################### 
# 
# 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_RD017
_database_code_depnum_ccdc_archive 'CCDC 2449926'
loop_
_audit_author_name
_audit_author_address
'Katherine Robertson'
;Saint Marys University
Canada
;
_audit_update_record             
;
2025-05-09 deposited with the CCDC.	2025-07-29 downloaded from the CCDC.
;

#============================================================================== 

_audit_creation_method           SHELXL-2019/3
_shelx_SHELXL_version_number     2019/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C16 H10 Cl2 N2)'
_chemical_formula_sum            'C16 H10 Cl2 N2'
_chemical_formula_weight         301.16

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'
Cl Cl 0.1484 0.1585 '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'

_space_group_crystal_system      trigonal
_space_group_IT_number           148
_space_group_name_H-M_alt        'R -3 :H'
_space_group_name_Hall           '-R 3'

_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'
'-y, x-y, z'
'-x+y, -x, z'
'x+2/3, y+1/3, z+1/3'
'-y+2/3, x-y+1/3, z+1/3'
'-x+y+2/3, -x+1/3, z+1/3'
'x+1/3, y+2/3, z+2/3'
'-y+1/3, x-y+2/3, z+2/3'
'-x+y+1/3, -x+2/3, z+2/3'
'-x, -y, -z'
'y, -x+y, -z'
'x-y, x, -z'
'-x+2/3, -y+1/3, -z+1/3'
'y+2/3, -x+y+1/3, -z+1/3'
'x-y+2/3, x+1/3, -z+1/3'
'-x+1/3, -y+2/3, -z+2/3'
'y+1/3, -x+y+2/3, -z+2/3'
'x-y+1/3, x+2/3, -z+2/3'

_cell_length_a                   31.997(5)
_cell_length_b                   31.997(5)
_cell_length_c                   7.0615(10)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                120
_cell_volume                     6261(2)
_cell_formula_units_Z            18
_cell_measurement_temperature    125(2)
_cell_measurement_reflns_used    9005
_cell_measurement_theta_min      2.20
_cell_measurement_theta_max      28.71

_exptl_crystal_description       block
_exptl_crystal_colour            'dark red'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.438
_exptl_crystal_F_000             2772
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.220
_exptl_absorpt_coefficient_mu    0.456
_shelx_estimated_absorpt_T_min   0.846
_shelx_estimated_absorpt_T_max   0.906
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7075
_exptl_absorpt_correction_T_max  0.7458
_exptl_absorpt_process_details   'SADABS; Bruker 2009'
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      125(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?

_diffrn_reflns_number            25536
_diffrn_reflns_av_unetI/netI     0.0114
_diffrn_reflns_av_R_equivalents  0.0187
_diffrn_reflns_limit_h_min       -43
_diffrn_reflns_limit_h_max       42
_diffrn_reflns_limit_k_min       -42
_diffrn_reflns_limit_k_max       42
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_theta_min         1.273
_diffrn_reflns_theta_max         28.882
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.963
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.963
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.963
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3533
_reflns_number_gt                3215
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2019/2 (Sheldrick, 2019)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0395P)²+8.7287P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     dual
_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         3533
_refine_ls_number_parameters     185
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0329
_refine_ls_R_factor_gt           0.0293
_refine_ls_wR_factor_ref         0.0794
_refine_ls_wR_factor_gt          0.0769
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_restrained_S_all      1.045
_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
Cl1 Cl 0.31450(2) 0.43517(2) 0.42909(4) 0.03111(9) Uani 1 1 d . . . . .
Cl2 Cl 0.44259(2) 0.48082(2) 1.00684(5) 0.02795(9) Uani 1 1 d . . . . .
N1 N 0.47270(3) 0.55984(3) 0.46681(14) 0.01611(19) Uani 1 1 d D . . . .
H1N H 0.5006(5) 0.5762(5) 0.411(2) 0.025(4) Uiso 1 1 d D . . . .
N2 N 0.47908(3) 0.48867(3) 0.54027(14) 0.01685(19) Uani 1 1 d . . . . .
C1 C 0.45551(4) 0.51467(4) 0.54371(16) 0.0163(2) Uani 1 1 d . . . . .
C2 C 0.41039(4) 0.50077(4) 0.62312(16) 0.0160(2) Uani 1 1 d . . . . .
C3 C 0.40114(4) 0.53883(4) 0.59256(16) 0.0167(2) Uani 1 1 d . . . . .
H3 H 0.372992 0.539447 0.630887 0.020 Uiso 1 1 calc R U . . .
C4 C 0.44027(4) 0.57536(4) 0.49664(15) 0.0154(2) Uani 1 1 d . . . . .
C5 C 0.37731(4) 0.45536(4) 0.72119(15) 0.0151(2) Uani 1 1 d . . . . .
C6 C 0.33155(4) 0.42324(4) 0.64684(16) 0.0172(2) Uani 1 1 d . . . . .
C7 C 0.29848(4) 0.38148(4) 0.74033(18) 0.0205(2) Uani 1 1 d . . . . .
H7 H 0.267853 0.360491 0.685608 0.025 Uiso 1 1 calc R U . . .
C8 C 0.31079(4) 0.37086(4) 0.91458(19) 0.0236(2) Uani 1 1 d . . . . .
H8 H 0.288360 0.342466 0.980068 0.028 Uiso 1 1 calc R U . . .
C9 C 0.35549(4) 0.40125(4) 0.99415(18) 0.0231(2) Uani 1 1 d . . . . .
H9 H 0.363885 0.393738 1.113300 0.028 Uiso 1 1 calc R U . . .
C10 C 0.38797(4) 0.44291(4) 0.89776(16) 0.0179(2) Uani 1 1 d . . . . .
C11 C 0.44755(4) 0.62190(4) 0.43300(15) 0.0156(2) Uani 1 1 d . . . . .
C12 C 0.41237(4) 0.63460(4) 0.47384(17) 0.0201(2) Uani 1 1 d . . . . .
H12 H 0.384526 0.613103 0.544402 0.024 Uiso 1 1 calc R U . . .
C13 C 0.41791(5) 0.67824(4) 0.41211(18) 0.0232(2) Uani 1 1 d . . . . .
H13 H 0.393756 0.686302 0.440259 0.028 Uiso 1 1 calc R U . . .
C14 C 0.45847(5) 0.71026(4) 0.30946(18) 0.0240(2) Uani 1 1 d . . . . .
H14 H 0.462307 0.740293 0.268929 0.029 Uiso 1 1 calc R U . . .
C15 C 0.49333(4) 0.69803(4) 0.26657(17) 0.0225(2) Uani 1 1 d . . . . .
H15 H 0.520930 0.719616 0.194978 0.027 Uiso 1 1 calc R U . . .
C16 C 0.48808(4) 0.65431(4) 0.32787(16) 0.0180(2) Uani 1 1 d . . . . .
H16 H 0.512230 0.646357 0.298117 0.022 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
Cl1 C6 1.7365(12) . ?
Cl2 C10 1.7318(12) . ?
N1 C4 1.3722(14) . ?
N1 C1 1.3754(14) . ?
N1 H1N 0.871(13) . ?
N2 N2 1.2923(18) 10_666 ?
N2 C1 1.3743(14) . ?
C1 C2 1.3981(15) . ?
C2 C3 1.4062(15) . ?
C2 C5 1.4742(15) . ?
C3 C4 1.3890(15) . ?
C3 H3 0.9500 . ?
C4 C11 1.4584(15) . ?
C5 C10 1.4020(16) . ?
C5 C6 1.4039(15) . ?
C6 C7 1.3883(16) . ?
C7 C8 1.3851(18) . ?
C7 H7 0.9500 . ?
C8 C9 1.3841(18) . ?
C8 H8 0.9500 . ?
C9 C10 1.3910(16) . ?
C9 H9 0.9500 . ?
C11 C16 1.4011(15) . ?
C11 C12 1.4047(16) . ?
C12 C13 1.3869(16) . ?
C12 H12 0.9500 . ?
C13 C14 1.3891(18) . ?
C13 H13 0.9500 . ?
C14 C15 1.3877(18) . ?
C14 H14 0.9500 . ?
C15 C16 1.3921(16) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C4 N1 C1 110.02(9) . . ?
C4 N1 H1N 125.8(10) . . ?
C1 N1 H1N 124.1(10) . . ?
N2 N2 C1 113.34(11) 10_666 . ?
N2 C1 N1 125.24(10) . . ?
N2 C1 C2 127.35(10) . . ?
N1 C1 C2 107.41(9) . . ?
C1 C2 C3 107.10(9) . . ?
C1 C2 C5 128.33(10) . . ?
C3 C2 C5 124.57(10) . . ?
C4 C3 C2 108.18(9) . . ?
C4 C3 H3 125.9 . . ?
C2 C3 H3 125.9 . . ?
N1 C4 C3 107.28(9) . . ?
N1 C4 C11 123.95(10) . . ?
C3 C4 C11 128.77(10) . . ?
C10 C5 C6 115.95(10) . . ?
C10 C5 C2 122.76(10) . . ?
C6 C5 C2 121.18(10) . . ?
C7 C6 C5 122.73(11) . . ?
C7 C6 Cl1 117.43(9) . . ?
C5 C6 Cl1 119.84(8) . . ?
C8 C7 C6 119.02(11) . . ?
C8 C7 H7 120.5 . . ?
C6 C7 H7 120.5 . . ?
C9 C8 C7 120.60(11) . . ?
C9 C8 H8 119.7 . . ?
C7 C8 H8 119.7 . . ?
C8 C9 C10 119.28(11) . . ?
C8 C9 H9 120.4 . . ?
C10 C9 H9 120.4 . . ?
C9 C10 C5 122.42(11) . . ?
C9 C10 Cl2 117.54(9) . . ?
C5 C10 Cl2 120.02(9) . . ?
C16 C11 C12 118.28(10) . . ?
C16 C11 C4 122.36(10) . . ?
C12 C11 C4 119.35(10) . . ?
C13 C12 C11 120.62(11) . . ?
C13 C12 H12 119.7 . . ?
C11 C12 H12 119.7 . . ?
C12 C13 C14 120.56(11) . . ?
C12 C13 H13 119.7 . . ?
C14 C13 H13 119.7 . . ?
C15 C14 C13 119.49(11) . . ?
C15 C14 H14 120.3 . . ?
C13 C14 H14 120.3 . . ?
C14 C15 C16 120.36(11) . . ?
C14 C15 H15 119.8 . . ?
C16 C15 H15 119.8 . . ?
C15 C16 C11 120.69(11) . . ?
C15 C16 H16 119.7 . . ?
C11 C16 H16 119.7 . . ?

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
N2 N2 C1 N1 1.59(18) 10_666 . . . ?
N2 N2 C1 C2 -178.74(12) 10_666 . . . ?
C4 N1 C1 N2 -179.56(11) . . . . ?
C4 N1 C1 C2 0.71(12) . . . . ?
N2 C1 C2 C3 -179.99(11) . . . . ?
N1 C1 C2 C3 -0.26(12) . . . . ?
N2 C1 C2 C5 -0.1(2) . . . . ?
N1 C1 C2 C5 179.59(11) . . . . ?
C1 C2 C3 C4 -0.26(13) . . . . ?
C5 C2 C3 C4 179.88(10) . . . . ?
C1 N1 C4 C3 -0.87(12) . . . . ?
C1 N1 C4 C11 179.91(10) . . . . ?
C2 C3 C4 N1 0.68(13) . . . . ?
C2 C3 C4 C11 179.85(11) . . . . ?
C1 C2 C5 C10 67.94(16) . . . . ?
C3 C2 C5 C10 -112.23(13) . . . . ?
C1 C2 C5 C6 -116.07(13) . . . . ?
C3 C2 C5 C6 63.76(15) . . . . ?
C10 C5 C6 C7 -0.17(16) . . . . ?
C2 C5 C6 C7 -176.42(10) . . . . ?
C10 C5 C6 Cl1 179.90(8) . . . . ?
C2 C5 C6 Cl1 3.65(14) . . . . ?
C5 C6 C7 C8 0.22(17) . . . . ?
Cl1 C6 C7 C8 -179.84(9) . . . . ?
C6 C7 C8 C9 -0.35(18) . . . . ?
C7 C8 C9 C10 0.42(18) . . . . ?
C8 C9 C10 C5 -0.38(18) . . . . ?
C8 C9 C10 Cl2 177.82(9) . . . . ?
C6 C5 C10 C9 0.25(16) . . . . ?
C2 C5 C10 C9 176.43(10) . . . . ?
C6 C5 C10 Cl2 -177.90(8) . . . . ?
C2 C5 C10 Cl2 -1.72(15) . . . . ?
N1 C4 C11 C16 2.64(17) . . . . ?
C3 C4 C11 C16 -176.40(11) . . . . ?
N1 C4 C11 C12 -178.92(10) . . . . ?
C3 C4 C11 C12 2.04(18) . . . . ?
C16 C11 C12 C13 -0.30(17) . . . . ?
C4 C11 C12 C13 -178.81(11) . . . . ?
C11 C12 C13 C14 -0.28(19) . . . . ?
C12 C13 C14 C15 0.84(19) . . . . ?
C13 C14 C15 C16 -0.82(19) . . . . ?
C14 C15 C16 C11 0.24(18) . . . . ?
C12 C11 C16 C15 0.32(17) . . . . ?
C4 C11 C16 C15 178.78(11) . . . . ?

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
N1 H1N N2 0.871(13) 2.490(16) 2.6809(14) 93.0(11) 10_666 yes
N1 H1N C7 0.871(13) 2.677(15) 3.2445(15) 123.9(13) 15_556 yes
N1 H1N C8 0.871(13) 2.978(14) 3.7668(16) 151.5(13) 15_556 yes

_refine_diff_density_max         0.404
_refine_diff_density_min         -0.279
_refine_diff_density_rms         0.047

