# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 2076682'
loop_
_audit_author_name
_audit_author_address
'Ray Butcher'
;Howard University
United States of America
;
_audit_update_record             
;
2021-04-11 deposited with the CCDC.	2024-05-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         
;
2(C14 H10 Cl2 N O2), C3 H12 N2, 3(H2 O)
;
_chemical_formula_sum            'C31 H38 Cl4 N4 O7'
_chemical_formula_weight         720.45

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

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

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

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

_cell_length_a                   9.4328(2)
_cell_length_b                   9.8482(3)
_cell_length_c                   18.3159(7)
_cell_angle_alpha                90.907(3)
_cell_angle_beta                 94.232(2)
_cell_angle_gamma                90.018(2)
_cell_volume                     1696.62(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7015
_cell_measurement_theta_min      2.1590
_cell_measurement_theta_max      29.3410

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.410
_exptl_crystal_F_000             752
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.240
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.401
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.91109
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.59a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_measurement_device_type  'XtaLAB Mini II'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_reflns_number            32176
_diffrn_reflns_av_unetI/netI     0.0543
_diffrn_reflns_av_R_equivalents  0.0338
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.068
_diffrn_reflns_theta_max         30.658
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.936
_diffrn_measured_fraction_theta_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.936
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.936
_diffrn_reflns_point_group_measured_fraction_full 0.991
_reflns_number_total             9830
_reflns_number_gt                6574
_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       'CrysAlisPro 1.171.40.59a (Rigaku OD, 2019)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.59a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.59a (Rigaku OD, 2019)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2015b)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_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)+(0.0511P)²+0.1922P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         9830
_refine_ls_number_parameters     461
_refine_ls_number_restraints     9
_refine_ls_R_factor_all          0.0807
_refine_ls_R_factor_gt           0.0437
_refine_ls_wR_factor_ref         0.1116
_refine_ls_wR_factor_gt          0.0981
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_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
Cl1A Cl 0.94450(4) 0.21368(5) 0.96036(3) 0.02754(11) Uani 1 1 d . . . . .
Cl2A Cl 1.17197(5) 0.46867(5) 0.73511(3) 0.03343(12) Uani 1 1 d . . . . .
O1A O 0.92832(13) 0.23350(14) 0.64379(7) 0.0319(3) Uani 1 1 d . . . . .
O2A O 0.86223(15) 0.03908(15) 0.58787(8) 0.0366(3) Uani 1 1 d . . . . .
N1A N 0.96843(15) 0.27988(16) 0.79943(9) 0.0246(3) Uani 1 1 d . . . . .
H1AA H 0.991(2) 0.282(2) 0.7586(11) 0.029(6) Uiso 1 1 d . . . . .
C1A C 1.05423(17) 0.35393(17) 0.85042(10) 0.0224(4) Uani 1 1 d . . . . .
C2A C 1.05342(17) 0.33627(17) 0.92593(10) 0.0231(4) Uani 1 1 d . . . . .
C3A C 1.13948(18) 0.40990(19) 0.97625(11) 0.0270(4) Uani 1 1 d . . . . .
H3AA H 1.133052 0.397266 1.027212 0.032 Uiso 1 1 calc R U . . .
C4A C 1.23580(19) 0.5028(2) 0.95178(11) 0.0290(4) Uani 1 1 d . . . . .
H4AA H 1.294108 0.555475 0.985995 0.035 Uiso 1 1 calc R U . . .
C5A C 1.24625(18) 0.51825(19) 0.87759(11) 0.0286(4) Uani 1 1 d . . . . .
H5AA H 1.314304 0.578964 0.860535 0.034 Uiso 1 1 calc R U . . .
C6A C 1.15755(18) 0.44517(18) 0.82841(10) 0.0250(4) Uani 1 1 d . . . . .
C7A C 0.81861(17) 0.26711(18) 0.80168(10) 0.0225(4) Uani 1 1 d . . . . .
C8A C 0.74085(18) 0.35495(19) 0.84329(10) 0.0258(4) Uani 1 1 d . . . . .
H8AA H 0.787859 0.426983 0.870399 0.031 Uiso 1 1 calc R U . . .
C9A C 0.59502(18) 0.3385(2) 0.84565(10) 0.0281(4) Uani 1 1 d . . . . .
H9AA H 0.542859 0.398274 0.874779 0.034 Uiso 1 1 calc R U . . .
C10A C 0.52616(18) 0.2352(2) 0.80564(11) 0.0297(4) Uani 1 1 d . . . . .
H10A H 0.426460 0.223308 0.807087 0.036 Uiso 1 1 calc R U . . .
C11A C 0.60327(18) 0.14884(19) 0.76333(10) 0.0274(4) Uani 1 1 d . . . . .
H11A H 0.554979 0.078634 0.735346 0.033 Uiso 1 1 calc R U . . .
C12A C 0.75022(18) 0.16217(18) 0.76069(10) 0.0234(4) Uani 1 1 d . . . . .
C13A C 0.83134(19) 0.06216(18) 0.71631(10) 0.0253(4) Uani 1 1 d . . . . .
H13A H 0.771148 -0.019156 0.705662 0.030 Uiso 1 1 calc R U . . .
H13B H 0.917075 0.032964 0.746419 0.030 Uiso 1 1 calc R U . . .
C14A C 0.87701(19) 0.1161(2) 0.64470(11) 0.0287(4) Uani 1 1 d . . . . .
Cl1B Cl 0.54383(4) 0.71344(5) 0.96440(3) 0.02712(11) Uani 1 1 d . . . . .
Cl2B Cl 0.25806(5) 0.96587(5) 0.73646(3) 0.03306(12) Uani 1 1 d . . . . .
O1B O 0.46035(14) 0.74300(14) 0.64648(7) 0.0330(3) Uani 1 1 d . . . . .
O2B O 0.60747(15) 0.61707(15) 0.58527(8) 0.0375(3) Uani 1 1 d . . . . .
N1B N 0.48188(15) 0.78161(16) 0.80266(9) 0.0239(3) Uani 1 1 d . . . . .
H1BA H 0.4478(19) 0.7825(18) 0.7574(11) 0.020(5) Uiso 1 1 d . . . . .
C1B C 0.40735(17) 0.85418(17) 0.85292(10) 0.0218(4) Uani 1 1 d . . . . .
C2B C 0.42668(17) 0.83650(17) 0.92884(10) 0.0224(4) Uani 1 1 d . . . . .
C3B C 0.35222(18) 0.90976(19) 0.97848(11) 0.0261(4) Uani 1 1 d . . . . .
H3BA H 0.371031 0.896991 1.029583 0.031 Uiso 1 1 calc R U . . .
C4B C 0.24979(18) 1.0021(2) 0.95293(11) 0.0285(4) Uani 1 1 d . . . . .
H4BA H 0.199768 1.054713 0.986510 0.034 Uiso 1 1 calc R U . . .
C5B C 0.22085(18) 1.01719(18) 0.87833(11) 0.0270(4) Uani 1 1 d . . . . .
H5BA H 0.147723 1.076942 0.860435 0.032 Uiso 1 1 calc R U . . .
C6B C 0.29843(18) 0.94529(18) 0.83029(10) 0.0238(4) Uani 1 1 d . . . . .
C7B C 0.63241(17) 0.76984(18) 0.80635(10) 0.0219(4) Uani 1 1 d . . . . .
C8B C 0.72056(18) 0.85406(19) 0.85109(10) 0.0253(4) Uani 1 1 d . . . . .
H8BA H 0.680197 0.922376 0.880289 0.030 Uiso 1 1 calc R U . . .
C9B C 0.86703(19) 0.8393(2) 0.85351(11) 0.0291(4) Uani 1 1 d . . . . .
H9BA H 0.926435 0.896752 0.884661 0.035 Uiso 1 1 calc R U . . .
C10B C 0.92667(19) 0.7411(2) 0.81070(11) 0.0324(5) Uani 1 1 d . . . . .
H10B H 1.026938 0.730226 0.812600 0.039 Uiso 1 1 calc R U . . .
C11B C 0.83922(19) 0.6586(2) 0.76497(11) 0.0299(4) Uani 1 1 d . . . . .
H11B H 0.880619 0.592874 0.734565 0.036 Uiso 1 1 calc R U . . .
C12B C 0.69162(18) 0.67007(18) 0.76267(10) 0.0237(4) Uani 1 1 d . . . . .
C13B C 0.59836(19) 0.57717(19) 0.71331(10) 0.0273(4) Uani 1 1 d . . . . .
H13C H 0.514166 0.549720 0.738782 0.033 Uiso 1 1 calc R U . . .
H13D H 0.651856 0.494180 0.701504 0.033 Uiso 1 1 calc R U . . .
C14B C 0.55063(19) 0.64990(19) 0.64297(11) 0.0274(4) Uani 1 1 d . . . . .
O1W O 0.73751(17) 0.38509(16) 0.56141(9) 0.0385(4) Uani 1 1 d D . . . .
H1W1 H 0.710(3) 0.462(2) 0.5769(18) 0.120(14) Uiso 1 1 d D . . . .
H1W2 H 0.801(3) 0.364(3) 0.5941(14) 0.095(12) Uiso 1 1 d D . . . .
O2W O 0.56352(18) 0.97397(16) 0.57934(9) 0.0416(4) Uani 1 1 d D . . . .
H2W1 H 0.6512(18) 0.972(3) 0.5896(19) 0.114(14) Uiso 1 1 d D . . . .
H2W2 H 0.531(3) 0.907(2) 0.6011(14) 0.070(9) Uiso 1 1 d D . . . .
O3W O 0.80775(17) 0.35333(19) 0.41896(11) 0.0469(4) Uani 1 1 d D . . . .
H3W1 H 0.740(3) 0.313(3) 0.3951(15) 0.101(13) Uiso 1 1 d D . . . .
H3W2 H 0.771(3) 0.370(4) 0.4599(12) 0.123(15) Uiso 1 1 d D . . . .
N1S N 0.98228(17) 0.81511(18) 0.51734(10) 0.0334(4) Uani 1 1 d . . . . .
H1SA H 1.043766 0.762019 0.544789 0.052(7) Uiso 1 1 calc R . . . .
H1SB H 0.950176 0.883274 0.545888 0.071(9) Uiso 1 1 calc R . . . .
H1SC H 1.027725 0.851223 0.480027 0.064(8) Uiso 1 1 calc R . . . .
C2S C 0.8592(2) 0.7309(2) 0.48659(12) 0.0340(5) Uani 1 1 d . . . . .
H2SA H 0.800492 0.704248 0.526668 0.033(6) Uiso 1 1 calc R . . . .
H2SB H 0.894863 0.647069 0.463773 0.044(6) Uiso 1 1 calc R . . . .
C3S C 0.7682(2) 0.8094(2) 0.42974(12) 0.0365(5) Uani 1 1 d . . . . .
H3SA H 0.745491 0.899606 0.450475 0.046(7) Uiso 1 1 calc R . . . .
H3SB H 0.823105 0.824073 0.386520 0.042(6) Uiso 1 1 calc R . . . .
C4S C 0.6306(2) 0.7361(2) 0.40552(11) 0.0383(5) Uani 1 1 d . . . . .
H4SA H 0.593101 0.770742 0.357465 0.055(7) Uiso 1 1 calc R . . . .
H4SB H 0.649754 0.637843 0.399631 0.046(7) Uiso 1 1 calc R . . . .
N5S N 0.52187(17) 0.75634(17) 0.46012(9) 0.0320(4) Uani 1 1 d . . . . .
H5SA H 0.439842 0.713381 0.443872 0.043(7) Uiso 1 1 calc R . . . .
H5SB H 0.504841 0.846681 0.465901 0.055(7) Uiso 1 1 calc R . . . .
H5SC H 0.554760 0.721289 0.503819 0.045(7) Uiso 1 1 calc R . . . .


_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
Cl1A C2A 1.7407(17) . ?
Cl2A C6A 1.7433(19) . ?
O1A C14A 1.254(2) . ?
O2A C14A 1.277(2) . ?
N1A C1A 1.388(2) . ?
N1A C7A 1.423(2) . ?
N1A H1AA 0.79(2) . ?
C1A C2A 1.397(2) . ?
C1A C6A 1.410(2) . ?
C2A C3A 1.379(2) . ?
C3A C4A 1.392(3) . ?
C3A H3AA 0.9500 . ?
C4A C5A 1.380(3) . ?
C4A H4AA 0.9500 . ?
C5A C6A 1.377(3) . ?
C5A H5AA 0.9500 . ?
C7A C8A 1.389(3) . ?
C7A C12A 1.397(3) . ?
C8A C9A 1.389(2) . ?
C8A H8AA 0.9500 . ?
C9A C10A 1.378(3) . ?
C9A H9AA 0.9500 . ?
C10A C11A 1.384(3) . ?
C10A H10A 0.9500 . ?
C11A C12A 1.397(2) . ?
C11A H11A 0.9500 . ?
C12A C13A 1.511(3) . ?
C13A C14A 1.514(3) . ?
C13A H13A 0.9900 . ?
C13A H13B 0.9900 . ?
Cl1B C2B 1.7418(17) . ?
Cl2B C6B 1.7477(18) . ?
O1B C14B 1.256(2) . ?
O2B C14B 1.258(2) . ?
N1B C1B 1.388(2) . ?
N1B C7B 1.421(2) . ?
N1B H1BA 0.867(19) . ?
C1B C2B 1.402(2) . ?
C1B C6B 1.408(2) . ?
C2B C3B 1.384(2) . ?
C3B C4B 1.388(2) . ?
C3B H3BA 0.9500 . ?
C4B C5B 1.384(3) . ?
C4B H4BA 0.9500 . ?
C5B C6B 1.374(3) . ?
C5B H5BA 0.9500 . ?
C7B C8B 1.389(3) . ?
C7B C12B 1.400(2) . ?
C8B C9B 1.387(2) . ?
C8B H8BA 0.9500 . ?
C9B C10B 1.381(3) . ?
C9B H9BA 0.9500 . ?
C10B C11B 1.385(3) . ?
C10B H10B 0.9500 . ?
C11B C12B 1.394(2) . ?
C11B H11B 0.9500 . ?
C12B C13B 1.511(3) . ?
C13B C14B 1.523(2) . ?
C13B H13C 0.9900 . ?
C13B H13D 0.9900 . ?
O1W H1W1 0.851(17) . ?
O1W H1W2 0.842(17) . ?
O2W H2W1 0.835(17) . ?
O2W H2W2 0.846(16) . ?
O3W H3W1 0.842(17) . ?
O3W H3W2 0.862(17) . ?
N1S C2S 1.497(2) . ?
N1S H1SA 0.9100 . ?
N1S H1SB 0.9100 . ?
N1S H1SC 0.9100 . ?
C2S C3S 1.521(3) . ?
C2S H2SA 0.9900 . ?
C2S H2SB 0.9900 . ?
C3S C4S 1.519(3) . ?
C3S H3SA 0.9900 . ?
C3S H3SB 0.9900 . ?
C4S N5S 1.496(3) . ?
C4S H4SA 0.9900 . ?
C4S H4SB 0.9900 . ?
N5S H5SA 0.9100 . ?
N5S H5SB 0.9100 . ?
N5S H5SC 0.9100 . ?

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
C1A N1A C7A 123.87(16) . . ?
C1A N1A H1AA 115.5(15) . . ?
C7A N1A H1AA 111.5(15) . . ?
N1A C1A C2A 123.26(16) . . ?
N1A C1A C6A 121.26(16) . . ?
C2A C1A C6A 115.28(16) . . ?
C3A C2A C1A 122.90(16) . . ?
C3A C2A Cl1A 116.88(14) . . ?
C1A C2A Cl1A 120.20(14) . . ?
C2A C3A C4A 119.48(18) . . ?
C2A C3A H3AA 120.3 . . ?
C4A C3A H3AA 120.3 . . ?
C5A C4A C3A 119.72(18) . . ?
C5A C4A H4AA 120.1 . . ?
C3A C4A H4AA 120.1 . . ?
C6A C5A C4A 119.69(17) . . ?
C6A C5A H5AA 120.2 . . ?
C4A C5A H5AA 120.2 . . ?
C5A C6A C1A 122.74(17) . . ?
C5A C6A Cl2A 118.52(14) . . ?
C1A C6A Cl2A 118.73(14) . . ?
C8A C7A C12A 120.16(16) . . ?
C8A C7A N1A 121.84(17) . . ?
C12A C7A N1A 118.00(16) . . ?
C7A C8A C9A 120.63(18) . . ?
C7A C8A H8AA 119.7 . . ?
C9A C8A H8AA 119.7 . . ?
C10A C9A C8A 119.85(18) . . ?
C10A C9A H9AA 120.1 . . ?
C8A C9A H9AA 120.1 . . ?
C9A C10A C11A 119.53(16) . . ?
C9A C10A H10A 120.2 . . ?
C11A C10A H10A 120.2 . . ?
C10A C11A C12A 121.76(18) . . ?
C10A C11A H11A 119.1 . . ?
C12A C11A H11A 119.1 . . ?
C11A C12A C7A 118.06(17) . . ?
C11A C12A C13A 120.08(17) . . ?
C7A C12A C13A 121.83(15) . . ?
C12A C13A C14A 114.78(15) . . ?
C12A C13A H13A 108.6 . . ?
C14A C13A H13A 108.6 . . ?
C12A C13A H13B 108.6 . . ?
C14A C13A H13B 108.6 . . ?
H13A C13A H13B 107.5 . . ?
O1A C14A O2A 122.92(18) . . ?
O1A C14A C13A 118.82(18) . . ?
O2A C14A C13A 118.26(17) . . ?
C1B N1B C7B 124.26(15) . . ?
C1B N1B H1BA 116.8(12) . . ?
C7B N1B H1BA 110.3(12) . . ?
N1B C1B C2B 123.47(15) . . ?
N1B C1B C6B 121.53(16) . . ?
C2B C1B C6B 114.85(16) . . ?
C3B C2B C1B 123.00(16) . . ?
C3B C2B Cl1B 116.87(14) . . ?
C1B C2B Cl1B 120.08(14) . . ?
C2B C3B C4B 119.38(18) . . ?
C2B C3B H3BA 120.3 . . ?
C4B C3B H3BA 120.3 . . ?
C5B C4B C3B 119.73(18) . . ?
C5B C4B H4BA 120.1 . . ?
C3B C4B H4BA 120.1 . . ?
C6B C5B C4B 119.63(16) . . ?
C6B C5B H5BA 120.2 . . ?
C4B C5B H5BA 120.2 . . ?
C5B C6B C1B 123.22(17) . . ?
C5B C6B Cl2B 118.39(13) . . ?
C1B C6B Cl2B 118.38(14) . . ?
C8B C7B C12B 119.85(16) . . ?
C8B C7B N1B 122.15(16) . . ?
C12B C7B N1B 118.00(16) . . ?
C9B C8B C7B 120.56(18) . . ?
C9B C8B H8BA 119.7 . . ?
C7B C8B H8BA 119.7 . . ?
C10B C9B C8B 120.11(18) . . ?
C10B C9B H9BA 119.9 . . ?
C8B C9B H9BA 119.9 . . ?
C9B C10B C11B 119.51(17) . . ?
C9B C10B H10B 120.2 . . ?
C11B C10B H10B 120.2 . . ?
C10B C11B C12B 121.33(18) . . ?
C10B C11B H11B 119.3 . . ?
C12B C11B H11B 119.3 . . ?
C11B C12B C7B 118.62(17) . . ?
C11B C12B C13B 120.34(17) . . ?
C7B C12B C13B 121.03(15) . . ?
C12B C13B C14B 109.90(15) . . ?
C12B C13B H13C 109.7 . . ?
C14B C13B H13C 109.7 . . ?
C12B C13B H13D 109.7 . . ?
C14B C13B H13D 109.7 . . ?
H13C C13B H13D 108.2 . . ?
O1B C14B O2B 123.62(17) . . ?
O1B C14B C13B 117.98(17) . . ?
O2B C14B C13B 118.35(16) . . ?
H1W1 O1W H1W2 102(2) . . ?
H2W1 O2W H2W2 105(2) . . ?
H3W1 O3W H3W2 102(2) . . ?
C2S N1S H1SA 109.5 . . ?
C2S N1S H1SB 109.5 . . ?
H1SA N1S H1SB 109.5 . . ?
C2S N1S H1SC 109.5 . . ?
H1SA N1S H1SC 109.5 . . ?
H1SB N1S H1SC 109.5 . . ?
N1S C2S C3S 110.86(16) . . ?
N1S C2S H2SA 109.5 . . ?
C3S C2S H2SA 109.5 . . ?
N1S C2S H2SB 109.5 . . ?
C3S C2S H2SB 109.5 . . ?
H2SA C2S H2SB 108.1 . . ?
C4S C3S C2S 112.48(17) . . ?
C4S C3S H3SA 109.1 . . ?
C2S C3S H3SA 109.1 . . ?
C4S C3S H3SB 109.1 . . ?
C2S C3S H3SB 109.1 . . ?
H3SA C3S H3SB 107.8 . . ?
N5S C4S C3S 111.11(18) . . ?
N5S C4S H4SA 109.4 . . ?
C3S C4S H4SA 109.4 . . ?
N5S C4S H4SB 109.4 . . ?
C3S C4S H4SB 109.4 . . ?
H4SA C4S H4SB 108.0 . . ?
C4S N5S H5SA 109.5 . . ?
C4S N5S H5SB 109.5 . . ?
H5SA N5S H5SB 109.5 . . ?
C4S N5S H5SC 109.5 . . ?
H5SA N5S H5SC 109.5 . . ?
H5SB N5S H5SC 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C7A N1A C1A C2A 52.3(2) . . . . ?
C7A N1A C1A C6A -133.10(18) . . . . ?
N1A C1A C2A C3A 179.72(16) . . . . ?
C6A C1A C2A C3A 4.8(2) . . . . ?
N1A C1A C2A Cl1A 1.7(2) . . . . ?
C6A C1A C2A Cl1A -173.25(12) . . . . ?
C1A C2A C3A C4A -2.4(3) . . . . ?
Cl1A C2A C3A C4A 175.67(13) . . . . ?
C2A C3A C4A C5A -1.4(3) . . . . ?
C3A C4A C5A C6A 2.4(3) . . . . ?
C4A C5A C6A C1A 0.2(3) . . . . ?
C4A C5A C6A Cl2A 179.18(14) . . . . ?
N1A C1A C6A C5A -178.72(16) . . . . ?
C2A C1A C6A C5A -3.7(2) . . . . ?
N1A C1A C6A Cl2A 2.3(2) . . . . ?
C2A C1A C6A Cl2A 177.35(12) . . . . ?
C1A N1A C7A C8A 17.1(3) . . . . ?
C1A N1A C7A C12A -162.61(16) . . . . ?
C12A C7A C8A C9A 1.0(3) . . . . ?
N1A C7A C8A C9A -178.70(16) . . . . ?
C7A C8A C9A C10A -0.9(3) . . . . ?
C8A C9A C10A C11A -0.1(3) . . . . ?
C9A C10A C11A C12A 0.9(3) . . . . ?
C10A C11A C12A C7A -0.7(3) . . . . ?
C10A C11A C12A C13A 177.42(16) . . . . ?
C8A C7A C12A C11A -0.3(2) . . . . ?
N1A C7A C12A C11A 179.48(15) . . . . ?
C8A C7A C12A C13A -178.34(15) . . . . ?
N1A C7A C12A C13A 1.4(2) . . . . ?
C11A C12A C13A C14A 104.81(19) . . . . ?
C7A C12A C13A C14A -77.2(2) . . . . ?
C12A C13A C14A O1A 43.5(2) . . . . ?
C12A C13A C14A O2A -136.94(17) . . . . ?
C7B N1B C1B C2B -51.9(2) . . . . ?
C7B N1B C1B C6B 132.66(18) . . . . ?
N1B C1B C2B C3B 179.74(16) . . . . ?
C6B C1B C2B C3B -4.5(2) . . . . ?
N1B C1B C2B Cl1B -2.7(2) . . . . ?
C6B C1B C2B Cl1B 172.98(12) . . . . ?
C1B C2B C3B C4B 2.3(3) . . . . ?
Cl1B C2B C3B C4B -175.29(14) . . . . ?
C2B C3B C4B C5B 1.7(3) . . . . ?
C3B C4B C5B C6B -3.0(3) . . . . ?
C4B C5B C6B C1B 0.6(3) . . . . ?
C4B C5B C6B Cl2B 179.52(14) . . . . ?
N1B C1B C6B C5B 178.91(16) . . . . ?
C2B C1B C6B C5B 3.1(2) . . . . ?
N1B C1B C6B Cl2B 0.0(2) . . . . ?
C2B C1B C6B Cl2B -175.85(12) . . . . ?
C1B N1B C7B C8B -14.7(3) . . . . ?
C1B N1B C7B C12B 165.74(16) . . . . ?
C12B C7B C8B C9B -0.7(3) . . . . ?
N1B C7B C8B C9B 179.74(16) . . . . ?
C7B C8B C9B C10B 0.6(3) . . . . ?
C8B C9B C10B C11B 0.6(3) . . . . ?
C9B C10B C11B C12B -1.8(3) . . . . ?
C10B C11B C12B C7B 1.7(3) . . . . ?
C10B C11B C12B C13B -178.90(16) . . . . ?
C8B C7B C12B C11B -0.5(2) . . . . ?
N1B C7B C12B C11B 179.13(16) . . . . ?
C8B C7B C12B C13B -179.86(15) . . . . ?
N1B C7B C12B C13B -0.3(2) . . . . ?
C11B C12B C13B C14B -98.90(19) . . . . ?
C7B C12B C13B C14B 80.5(2) . . . . ?
C12B C13B C14B O1B -71.9(2) . . . . ?
C12B C13B C14B O2B 105.5(2) . . . . ?
N1S C2S C3S C4S -171.42(17) . . . . ?
C2S C3S C4S N5S 79.9(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
N1A H1AA Cl2A 0.79(2) 2.57(2) 2.9885(16) 114.4(17) . yes
N1A H1AA O1A 0.79(2) 2.19(2) 2.877(2) 145.8(19) . yes
N1B H1BA Cl2B 0.867(19) 2.556(18) 2.9857(15) 111.6(14) . yes
N1B H1BA O1B 0.867(19) 2.075(19) 2.872(2) 152.6(16) . yes
O1W H1W1 O2B 0.851(17) 1.819(18) 2.639(2) 161(3) . yes
O1W H1W2 O1A 0.842(17) 1.949(19) 2.723(2) 152(3) . yes
O2W H2W1 O2A 0.835(17) 2.098(18) 2.882(2) 156(3) 1_565 yes
O2W H2W2 O1B 0.846(16) 1.966(16) 2.810(2) 176(3) . yes
O3W H3W1 O1B 0.842(17) 2.06(2) 2.872(2) 162(3) 2_666 yes
O3W H3W2 O1W 0.862(17) 1.912(19) 2.752(3) 164(4) . yes
N1S H1SA O3W 0.91 1.89 2.785(2) 166.6 2_766 yes
N1S H1SB O2A 0.91 1.92 2.818(2) 168.3 1_565 yes
N1S H1SC O1A 0.91 2.47 3.158(2) 132.9 2_766 yes
N1S H1SC O2A 0.91 2.01 2.903(2) 168.6 2_766 yes
C2S H2SA O2B 0.99 2.35 3.295(2) 159.4 . yes
C3S H3SB O1A 0.99 2.51 3.277(2) 133.9 2_766 yes
N5S H5SA O1W 0.91 1.93 2.814(2) 163.8 2_666 yes
N5S H5SB O2W 0.91 2.44 3.040(2) 123.8 . yes
N5S H5SB O2W 0.91 2.05 2.864(2) 148.7 2_676 yes
N5S H5SC O2B 0.91 1.86 2.759(2) 168.5 . yes

_refine_diff_density_max         0.360
_refine_diff_density_min         -0.304
_refine_diff_density_rms         0.061

####################################################################### 
# 
# 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_exp_351_jrb1-022_auto
_database_code_depnum_ccdc_archive 'CCDC 2210151'
loop_
_audit_author_name
_audit_author_address
'Christopher Richardson'
;University of Wollongong
Australia
;
_audit_update_record             
;
2024-05-13 deposited with the CCDC.	2024-05-23 downloaded from the CCDC.
;
_audit_creation_date             2024-05-12
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C14 H10 Cl2 N O2), C3 H12 N2, 2(C H4 O)'
_chemical_formula_sum            'C33 H40 Cl4 N4 O6'
_chemical_formula_weight         730.49
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.6753(3)
_cell_length_b                   9.9173(3)
_cell_length_c                   19.0010(5)
_cell_angle_alpha                88.365(2)
_cell_angle_beta                 79.728(3)
_cell_angle_gamma                88.551(3)
_cell_volume                     1792.87(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    12822
_cell_measurement_temperature    294(1)
_cell_measurement_theta_max      29.4990
_cell_measurement_theta_min      2.0540
_shelx_estimated_absorpt_T_max   0.879
_shelx_estimated_absorpt_T_min   0.805
_exptl_absorpt_coefficient_mu    0.378
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.85697
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.123a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.353
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             764
_exptl_crystal_recrystallization_method methanol
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.6
_exptl_crystal_size_min          0.35
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0250
_diffrn_reflns_av_unetI/netI     0.0235
_diffrn_reflns_Laue_measured_fraction_full 0.991
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            34574
_diffrn_reflns_point_group_measured_fraction_full 0.991
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.282
_diffrn_reflns_theta_min         2.055
_diffrn_ambient_temperature      294.0(10)
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -74.00 110.00   0.50   15.00    --   20.00  54.00-135.01  368
  2  ω    -74.00 110.00   0.50   15.00    --   20.00  54.00 -30.00  368
  3  ω    -74.00 110.00   0.50   15.00    --   20.00  54.00  97.79  368
  4  ω    -74.00 110.00   0.50   15.00    --   20.00  54.00  30.00  368
  5  ω    -74.00 110.00   0.50   15.00    --   20.00  54.00 155.61  368
  6  ω    -74.00 110.00   0.50   15.00    --   20.00  54.00-123.89  368
  7  ω    -74.00  26.00   0.50   15.00    --   20.00  54.00 -60.00  200
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini II'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6465
_reflns_number_total             8719
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.289
_refine_diff_density_min         -0.329
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     482
_refine_ls_number_reflns         8719
_refine_ls_number_restraints     50
_refine_ls_R_factor_all          0.0629
_refine_ls_R_factor_gt           0.0438
_refine_ls_restrained_S_all      1.035
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0547P)²+0.6399P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1159
_refine_ls_wR_factor_ref         0.1265
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H,H,H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2. Restrained distances
 N7-H7
 0.85 with sigma of 0.02
 N41-C17
 1.45 with sigma of 0.02
 N45-C19
 1.45 with sigma of 0.02
 C18-C17
 1.55 with sigma of 0.02
 C19-C18
 1.55 with sigma of 0.02
 N26-H26
 0.85 with sigma of 0.02
 O6A-C7A = O6-C7
 1.35 with sigma of 0.02
3. Uiso/Uaniso restraints and constraints
Uanis(C42) = Uanis(C17)
Uanis(C43) = Uanis(C18)
Uanis(C44) = Uanis(C19)
Uanis(C7) = Uanis(C7A)
4. Rigid body (RIGU) restrains
 C19, N45, H45A, H45B, H45C, H45D, H45E, H45F, C44, C43, H44A, H44B, H19A,
 H19B, C18, H43A, H43B, C42, H18A, H18B, C17, H42A, H42B, N41, H17A, H17B
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(O2)=Sof(O4)=1-FVAR(1)
 Sof(O1)=Sof(O3)=FVAR(1)
 Sof(H45D)=Sof(H45E)=Sof(H45F)=Sof(H41D)=Sof(H41E)=Sof(H41F)=Sof(C19)=
 Sof(H19A)=Sof(H19B)=Sof(C18)=Sof(H18A)=Sof(H18B)=Sof(C17)=Sof(H17A)=Sof(H17B)=
 1-FVAR(2)
 Sof(H45A)=Sof(H45B)=Sof(H45C)=Sof(H41A)=Sof(H41B)=Sof(H41C)=Sof(C43)=
 Sof(H43A)=Sof(H43B)=Sof(C44)=Sof(H44A)=Sof(H44B)=Sof(C42)=Sof(H42A)=Sof(H42B)=
 FVAR(2)
 Sof(O6A)=Sof(H6A)=Sof(C7A)=Sof(H7AA)=Sof(H7AB)=Sof(H7AC)=1-FVAR(3)
 Sof(O6)=Sof(H6)=Sof(C7)=Sof(H7A)=Sof(H7B)=Sof(H7C)=FVAR(3)
6.a Secondary CH2 refined with riding coordinates:
 C14(H14A,H14B), C33(H33A,H33B), C43(H43A,H43B), C44(H44A,H44B), C42(H42A,
 H42B), C19(H19A,H19B), C18(H18A,H18B), C17(H17A,H17B)
6.b Me refined with riding coordinates:
 N41(H41A,H41B,H41C)
6.c Aromatic/amide H refined with riding coordinates:
 C13(H13), C12(H12), C5(H5), C3(H3), C28(H28), C4(H4), C11(H11), C10(H10),
 C22(H22), C31(H31), C29(H29), C30(H30), C23(H23), C24(H24)
6.d Idealised Me refined as rotating group:
 N45(H45A,H45B,H45C), N45(H45D,H45E,H45F), N41(H41D,H41E,H41F), C7(H7A,H7B,
 H7C), C16(H16A,H16B,H16C), C7A(H7AA,H7AB,H7AC)
6.e Idealised tetrahedral OH refined as rotating group:
 O5(H5A), O6(H6), O6A(H6A)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl18 Cl 0.45759(5) 0.79751(5) 0.95930(3) 0.05466(14) Uani 1 1 d . . . . .
Cl39 Cl 0.94033(6) 0.72528(6) 0.04245(3) 0.05592(14) Uani 1 1 d . . . . .
Cl19 Cl 0.78954(6) 0.52217(7) 0.74669(3) 0.06808(17) Uani 1 1 d . . . . .
Cl40 Cl 1.10643(7) 0.93727(8) 0.27331(4) 0.0844(2) Uani 1 1 d . . . . .
O17 O 0.4963(2) 0.88757(16) 0.58320(7) 0.0738(5) Uani 1 1 d . . . . .
N7 N 0.54862(16) 0.70738(17) 0.80334(8) 0.0449(4) Uani 1 1 d D . . . .
O16 O 0.5573(2) 0.71319(16) 0.64646(8) 0.0757(5) Uani 1 1 d . . . . .
N26 N 0.92163(18) 0.76989(19) 0.20229(9) 0.0535(4) Uani 1 1 d D . . . .
C1 C 0.61427(17) 0.64447(17) 0.85547(8) 0.0373(3) Uani 1 1 d . . . . .
C8 C 0.40021(18) 0.71998(18) 0.80824(8) 0.0391(4) Uani 1 1 d . . . . .
C2 C 0.58084(18) 0.67250(18) 0.92872(9) 0.0393(4) Uani 1 1 d . . . . .
C6 C 0.72893(18) 0.55338(19) 0.83682(9) 0.0419(4) Uani 1 1 d . . . . .
C9 C 0.3469(2) 0.81615(18) 0.76376(9) 0.0427(4) Uani 1 1 d . . . . .
C27 C 0.7758(2) 0.76619(19) 0.19991(9) 0.0441(4) Uani 1 1 d . . . . .
C13 C 0.3079(2) 0.6391(2) 0.85494(9) 0.0450(4) Uani 1 1 d . . . . .
H13 H 0.343364 0.572746 0.882827 0.054 Uiso 1 1 calc R U . . .
C32 C 0.6955(2) 0.66449(19) 0.23953(10) 0.0477(4) Uani 1 1 d . . . . .
N45 N 0.7522(2) 0.5781(2) 0.54834(10) 0.0715(5) Uani 1 1 d D . . . .
H45A H 0.740473 0.588986 0.503107 0.086 Uiso 0.894(4) 1 calc R U P A 1
H45B H 0.833578 0.613128 0.553383 0.086 Uiso 0.894(4) 1 calc R U P A 1
H45C H 0.682219 0.619762 0.576932 0.086 Uiso 0.894(4) 1 calc R U P A 1
H45D H 0.833569 0.567329 0.563708 0.086 Uiso 0.106(4) 1 calc R U P A 2
H45E H 0.710841 0.655190 0.564386 0.086 Uiso 0.106(4) 1 calc R U P A 2
H45F H 0.767804 0.580246 0.500723 0.086 Uiso 0.106(4) 1 calc R U P A 2
C12 C 0.1639(2) 0.6562(2) 0.86032(10) 0.0518(5) Uani 1 1 d . . . . .
H12 H 0.103383 0.602186 0.892079 0.062 Uiso 1 1 calc R U . . .
N41 N 0.4943(3) 0.1621(2) 0.55837(10) 0.0790(7) Uani 1 1 d D . . . .
H41A H 0.490686 0.076151 0.573338 0.095 Uiso 0.894(4) 1 calc R U P A 1
H41B H 0.417565 0.206266 0.579532 0.095 Uiso 0.894(4) 1 calc R U P A 1
H41C H 0.498850 0.166352 0.511159 0.095 Uiso 0.894(4) 1 calc R U P A 1
H41D H 0.472307 0.078825 0.574540 0.095 Uiso 0.106(4) 1 calc R U P A 2
H41E H 0.485735 0.170006 0.512556 0.095 Uiso 0.106(4) 1 calc R U P A 2
H41F H 0.436623 0.221229 0.583765 0.095 Uiso 0.106(4) 1 calc R U P A 2
C5 C 0.7982(2) 0.4898(2) 0.88635(11) 0.0485(4) Uani 1 1 d . . . . .
H5 H 0.873568 0.430995 0.871508 0.058 Uiso 1 1 calc R U . . .
C20 C 1.01829(19) 0.84640(19) 0.15584(10) 0.0458(4) Uani 1 1 d . . . . .
C21 C 1.0362(2) 0.8393(2) 0.08130(11) 0.0476(4) Uani 1 1 d . . . . .
C3 C 0.6479(2) 0.6065(2) 0.97927(10) 0.0480(4) Uani 1 1 d . . . . .
H3 H 0.620511 0.624884 1.027535 0.058 Uiso 1 1 calc R U . . .
C28 C 0.7113(2) 0.8597(2) 0.15895(10) 0.0496(4) Uani 1 1 d . . . . .
H28 H 0.763765 0.928564 0.133754 0.060 Uiso 1 1 calc R U . . .
C15 C 0.5037(2) 0.8275(2) 0.64144(9) 0.0495(4) Uani 1 1 d . . . . .
C14 C 0.4441(2) 0.90176(19) 0.71013(10) 0.0514(5) Uani 1 1 d . . . . .
H14A H 0.521252 0.930431 0.732075 0.062 Uiso 1 1 calc R U . . .
H14B H 0.393027 0.982013 0.697982 0.062 Uiso 1 1 calc R U . . .
C4 C 0.7548(2) 0.5141(2) 0.95802(11) 0.0530(5) Uani 1 1 d . . . . .
H4 H 0.797559 0.468147 0.991996 0.064 Uiso 1 1 calc R U . . .
C11 C 0.1100(2) 0.7533(2) 0.81858(12) 0.0588(5) Uani 1 1 d . . . . .
H11 H 0.013457 0.766563 0.822733 0.071 Uiso 1 1 calc R U . . .
C10 C 0.2018(2) 0.8309(2) 0.77038(11) 0.0545(5) Uani 1 1 d . . . . .
H10 H 0.165200 0.894740 0.741562 0.065 Uiso 1 1 calc R U . . .
C33 C 0.7609(3) 0.5620(2) 0.28500(10) 0.0550(5) Uani 1 1 d . . . . .
H33A H 0.848919 0.528687 0.257708 0.066 Uiso 1 1 calc R U . . .
H33B H 0.698832 0.486143 0.296256 0.066 Uiso 1 1 calc R U . . .
C22 C 1.1320(2) 0.9175(2) 0.03535(13) 0.0607(6) Uani 1 1 d . . . . .
H22 H 1.137781 0.912627 -0.013892 0.073 Uiso 1 1 calc R U . . .
C31 C 0.5535(2) 0.6593(2) 0.23541(12) 0.0607(5) Uani 1 1 d . . . . .
H31 H 0.499377 0.592594 0.261566 0.073 Uiso 1 1 calc R U . . .
C29 C 0.5695(2) 0.8506(2) 0.15561(12) 0.0585(5) Uani 1 1 d . . . . .
H29 H 0.528110 0.912497 0.127624 0.070 Uiso 1 1 calc R U . . .
C25 C 1.1135(2) 0.9309(2) 0.18121(13) 0.0564(5) Uani 1 1 d . . . . .
C35 C 0.7885(3) 0.6199(2) 0.35421(11) 0.0582(5) Uani 1 1 d . . . . .
C30 C 0.4898(2) 0.7503(3) 0.19358(14) 0.0681(6) Uani 1 1 d . . . . .
H30 H 0.395050 0.743654 0.191211 0.082 Uiso 1 1 calc R U . . .
C23 C 1.2177(2) 1.0018(3) 0.06270(17) 0.0710(7) Uani 1 1 d . . . . .
H23 H 1.280529 1.055580 0.032091 0.085 Uiso 1 1 calc R U . . .
C24 C 1.2111(2) 1.0069(2) 0.13571(17) 0.0692(7) Uani 1 1 d . . . . .
H24 H 1.272076 1.061297 0.154300 0.083 Uiso 1 1 calc R U . . .
C43 C 0.6239(4) 0.3712(3) 0.55058(15) 0.0760(9) Uani 0.894(4) 1 d . . P A 1
H43A H 0.625717 0.376591 0.499371 0.091 Uiso 0.894(4) 1 calc R U P A 1
H43B H 0.541245 0.420180 0.574069 0.091 Uiso 0.894(4) 1 calc R U P A 1
C44 C 0.7529(4) 0.4320(3) 0.56767(16) 0.0834(10) Uani 0.894(4) 1 d . . P A 1
H44A H 0.755017 0.419709 0.618303 0.100 Uiso 0.894(4) 1 calc R U P A 1
H44B H 0.835784 0.387949 0.540980 0.100 Uiso 0.894(4) 1 calc R U P A 1
C42 C 0.6181(5) 0.2232(3) 0.5765(2) 0.0869(11) Uani 0.894(4) 1 d . . P A 1
H42A H 0.701993 0.174834 0.553874 0.104 Uiso 0.894(4) 1 calc R U P A 1
H42B H 0.614071 0.218008 0.627831 0.104 Uiso 0.894(4) 1 calc R U P A 1
O1 O 0.7001(3) 0.6328(3) 0.40652(13) 0.0699(10) Uani 0.606(4) 1 d . . P B 1
O3 O 0.9190(3) 0.6554(4) 0.35238(15) 0.0853(12) Uani 0.606(4) 1 d . . P B 1
O2 O 0.7828(6) 0.7439(5) 0.3615(2) 0.0870(19) Uani 0.394(4) 1 d . . P B 2
O4 O 0.7822(7) 0.5378(6) 0.4053(2) 0.093(2) Uani 0.394(4) 1 d . . P B 2
O5 O 0.9589(4) 0.8321(4) 0.45356(17) 0.1479(11) Uani 1 1 d . . . . .
H5A H 0.940897 0.781952 0.423003 0.222 Uiso 1 1 calc R U . . .
O6 O 0.9961(5) 0.3817(11) 0.4083(3) 0.115(2) Uani 0.672(15) 1 d D . P C 1
H6 H 0.948564 0.450415 0.404909 0.172 Uiso 0.672(15) 1 calc R U P C 1
C7 C 0.9400(13) 0.2762(13) 0.3778(6) 0.125(3) Uani 0.672(15) 1 d D . P C 1
H7A H 0.864931 0.237859 0.411759 0.188 Uiso 0.672(15) 1 calc R U P C 1
H7B H 1.011625 0.208498 0.363999 0.188 Uiso 0.672(15) 1 calc R U P C 1
H7C H 0.904328 0.308831 0.336298 0.188 Uiso 0.672(15) 1 calc R U P C 1
C16 C 0.8512(6) 0.9279(5) 0.4696(4) 0.179(2) Uani 1 1 d . . . . .
H16A H 0.876980 0.992564 0.501353 0.269 Uiso 1 1 calc R U . . .
H16B H 0.766835 0.884069 0.492255 0.269 Uiso 1 1 calc R U . . .
H16C H 0.835306 0.973039 0.426316 0.269 Uiso 1 1 calc R U . . .
H7 H 0.594(2) 0.698(2) 0.7607(9) 0.050(6) Uiso 1 1 d D . . . .
H26 H 0.936(3) 0.753(3) 0.2447(10) 0.071(7) Uiso 1 1 d D . . . .
C19 C 0.658(3) 0.4614(18) 0.5759(13) 0.0834(10) Uani 0.106(4) 1 d D . P A 2
H19A H 0.566502 0.477740 0.562340 0.100 Uiso 0.106(4) 1 calc R U P A 2
H19B H 0.643856 0.457884 0.627776 0.100 Uiso 0.106(4) 1 calc R U P A 2
C18 C 0.716(3) 0.325(2) 0.5474(13) 0.0760(9) Uani 0.106(4) 1 d D . P A 2
H18A H 0.807462 0.312898 0.561649 0.091 Uiso 0.106(4) 1 calc R U P A 2
H18B H 0.734219 0.334408 0.495682 0.091 Uiso 0.106(4) 1 calc R U P A 2
C17 C 0.640(2) 0.189(3) 0.565(2) 0.0869(11) Uani 0.106(4) 1 d D . P A 2
H17A H 0.697869 0.121766 0.536797 0.104 Uiso 0.106(4) 1 calc R U P A 2
H17B H 0.646458 0.166833 0.614797 0.104 Uiso 0.106(4) 1 calc R U P A 2
O6A O 1.0140(12) 0.6917(16) 0.5659(7) 0.106(3) Uani 0.328(15) 1 d D . P C 2
H6A H 0.984043 0.738063 0.535222 0.159 Uiso 0.328(15) 1 calc R U P C 2
C7A C 0.994(3) 0.758(3) 0.6279(12) 0.125(3) Uani 0.328(15) 1 d D . P C 2
H7AA H 1.067247 0.822345 0.626566 0.188 Uiso 0.328(15) 1 calc R U P C 2
H7AB H 0.995609 0.695242 0.666959 0.188 Uiso 0.328(15) 1 calc R U P C 2
H7AC H 0.904595 0.805090 0.634212 0.188 Uiso 0.328(15) 1 calc R U P C 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cl18 C2 1.7366(18) . ?
Cl39 C21 1.740(2) . ?
Cl19 C6 1.7422(18) . ?
Cl40 C25 1.742(2) . ?
O17 C15 1.254(2) . ?
N7 C1 1.394(2) . ?
N7 C8 1.425(2) . ?
N7 H7 0.856(15) . ?
O16 C15 1.243(2) . ?
N26 C27 1.422(2) . ?
N26 C20 1.390(3) . ?
N26 H26 0.852(16) . ?
C1 C2 1.406(2) . ?
C1 C6 1.414(2) . ?
C8 C9 1.405(2) . ?
C8 C13 1.394(3) . ?
C2 C3 1.392(2) . ?
C6 C5 1.380(3) . ?
C9 C14 1.514(3) . ?
C9 C10 1.391(3) . ?
C27 C32 1.405(3) . ?
C27 C28 1.399(3) . ?
C13 H13 0.9300 . ?
C13 C12 1.385(3) . ?
C32 C33 1.514(3) . ?
C32 C31 1.392(3) . ?
N45 H45A 0.8900 . ?
N45 H45B 0.8900 . ?
N45 H45C 0.8900 . ?
N45 H45D 0.8900 . ?
N45 H45E 0.8900 . ?
N45 H45F 0.8900 . ?
N45 C44 1.485(4) . ?
N45 C19 1.517(18) . ?
C12 H12 0.9300 . ?
C12 C11 1.381(3) . ?
N41 H41A 0.8900 . ?
N41 H41B 0.8900 . ?
N41 H41C 0.8900 . ?
N41 H41D 0.8900 . ?
N41 H41E 0.8900 . ?
N41 H41F 0.8900 . ?
N41 C42 1.455(5) . ?
N41 C17 1.472(19) . ?
C5 H5 0.9300 . ?
C5 C4 1.378(3) . ?
C20 C21 1.400(3) . ?
C20 C25 1.416(3) . ?
C21 C22 1.391(3) . ?
C3 H3 0.9300 . ?
C3 C4 1.377(3) . ?
C28 H28 0.9300 . ?
C28 C29 1.390(3) . ?
C15 C14 1.531(3) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C4 H4 0.9300 . ?
C11 H11 0.9300 . ?
C11 C10 1.387(3) . ?
C10 H10 0.9300 . ?
C33 H33A 0.9700 . ?
C33 H33B 0.9700 . ?
C33 C35 1.519(3) . ?
C22 H22 0.9300 . ?
C22 C23 1.367(4) . ?
C31 H31 0.9300 . ?
C31 C30 1.390(3) . ?
C29 H29 0.9300 . ?
C29 C30 1.380(3) . ?
C25 C24 1.384(3) . ?
C35 O1 1.198(3) . ?
C35 O3 1.313(4) . ?
C35 O2 1.240(5) . ?
C35 O4 1.243(5) . ?
C30 H30 0.9300 . ?
C23 H23 0.9300 . ?
C23 C24 1.380(4) . ?
C24 H24 0.9300 . ?
C43 H43A 0.9700 . ?
C43 H43B 0.9700 . ?
C43 C44 1.490(5) . ?
C43 C42 1.534(5) . ?
C44 H44A 0.9700 . ?
C44 H44B 0.9700 . ?
C42 H42A 0.9700 . ?
C42 H42B 0.9700 . ?
O5 H5A 0.8200 . ?
O5 C16 1.391(5) . ?
O6 H6 0.8200 . ?
O6 C7 1.380(10) . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C19 C18 1.533(18) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C18 C17 1.553(19) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
O6A H6A 0.8200 . ?
O6A C7A 1.349(16) . ?
C7A H7AA 0.9600 . ?
C7A H7AB 0.9600 . ?
C7A H7AC 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N7 C8 124.13(14) . . ?
C1 N7 H7 113.6(14) . . ?
C8 N7 H7 114.3(14) . . ?
C27 N26 H26 110.4(17) . . ?
C20 N26 C27 124.57(16) . . ?
C20 N26 H26 119.1(17) . . ?
N7 C1 C2 123.90(16) . . ?
N7 C1 C6 121.23(15) . . ?
C2 C1 C6 114.70(15) . . ?
C9 C8 N7 118.39(16) . . ?
C13 C8 N7 121.94(15) . . ?
C13 C8 C9 119.66(17) . . ?
C1 C2 Cl18 120.66(13) . . ?
C3 C2 Cl18 117.10(14) . . ?
C3 C2 C1 122.19(17) . . ?
C1 C6 Cl19 118.79(13) . . ?
C5 C6 Cl19 117.81(14) . . ?
C5 C6 C1 123.38(16) . . ?
C8 C9 C14 121.19(17) . . ?
C10 C9 C8 118.10(18) . . ?
C10 C9 C14 120.71(17) . . ?
C32 C27 N26 118.50(17) . . ?
C28 C27 N26 121.83(18) . . ?
C28 C27 C32 119.67(18) . . ?
C8 C13 H13 119.6 . . ?
C12 C13 C8 120.81(18) . . ?
C12 C13 H13 119.6 . . ?
C27 C32 C33 121.32(18) . . ?
C31 C32 C27 118.16(19) . . ?
C31 C32 C33 120.51(19) . . ?
H45A N45 H45B 109.5 . . ?
H45A N45 H45C 109.5 . . ?
H45B N45 H45C 109.5 . . ?
H45D N45 H45E 109.5 . . ?
H45D N45 H45F 109.5 . . ?
H45E N45 H45F 109.5 . . ?
C44 N45 H45A 109.5 . . ?
C44 N45 H45B 109.5 . . ?
C44 N45 H45C 109.5 . . ?
C19 N45 H45D 109.5 . . ?
C19 N45 H45E 109.5 . . ?
C19 N45 H45F 109.5 . . ?
C13 C12 H12 120.0 . . ?
C11 C12 C13 120.1(2) . . ?
C11 C12 H12 120.0 . . ?
H41A N41 H41B 109.5 . . ?
H41A N41 H41C 109.5 . . ?
H41B N41 H41C 109.5 . . ?
H41D N41 H41E 109.5 . . ?
H41D N41 H41F 109.5 . . ?
H41E N41 H41F 109.5 . . ?
C42 N41 H41A 109.5 . . ?
C42 N41 H41B 109.5 . . ?
C42 N41 H41C 109.5 . . ?
C17 N41 H41D 109.5 . . ?
C17 N41 H41E 109.5 . . ?
C17 N41 H41F 109.5 . . ?
C6 C5 H5 120.3 . . ?
C4 C5 C6 119.36(18) . . ?
C4 C5 H5 120.3 . . ?
N26 C20 C21 123.28(17) . . ?
N26 C20 C25 121.71(19) . . ?
C21 C20 C25 114.87(18) . . ?
C20 C21 Cl39 120.07(15) . . ?
C22 C21 Cl39 117.14(17) . . ?
C22 C21 C20 122.8(2) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 C2 120.18(17) . . ?
C4 C3 H3 119.9 . . ?
C27 C28 H28 119.7 . . ?
C29 C28 C27 120.5(2) . . ?
C29 C28 H28 119.7 . . ?
O17 C15 C14 117.21(18) . . ?
O16 C15 O17 124.12(18) . . ?
O16 C15 C14 118.67(16) . . ?
C9 C14 C15 113.06(16) . . ?
C9 C14 H14A 109.0 . . ?
C9 C14 H14B 109.0 . . ?
C15 C14 H14A 109.0 . . ?
C15 C14 H14B 109.0 . . ?
H14A C14 H14B 107.8 . . ?
C5 C4 H4 120.0 . . ?
C3 C4 C5 119.94(17) . . ?
C3 C4 H4 120.0 . . ?
C12 C11 H11 120.4 . . ?
C12 C11 C10 119.16(19) . . ?
C10 C11 H11 120.4 . . ?
C9 C10 H10 118.9 . . ?
C11 C10 C9 122.11(18) . . ?
C11 C10 H10 118.9 . . ?
C32 C33 H33A 109.0 . . ?
C32 C33 H33B 109.0 . . ?
C32 C33 C35 112.77(17) . . ?
H33A C33 H33B 107.8 . . ?
C35 C33 H33A 109.0 . . ?
C35 C33 H33B 109.0 . . ?
C21 C22 H22 120.1 . . ?
C23 C22 C21 119.9(2) . . ?
C23 C22 H22 120.1 . . ?
C32 C31 H31 118.8 . . ?
C30 C31 C32 122.3(2) . . ?
C30 C31 H31 118.8 . . ?
C28 C29 H29 119.8 . . ?
C30 C29 C28 120.4(2) . . ?
C30 C29 H29 119.8 . . ?
C20 C25 Cl40 118.00(17) . . ?
C24 C25 Cl40 119.54(18) . . ?
C24 C25 C20 122.5(2) . . ?
O1 C35 C33 123.7(3) . . ?
O1 C35 O3 122.0(3) . . ?
O3 C35 C33 114.3(2) . . ?
O2 C35 C33 119.4(3) . . ?
O2 C35 O4 123.2(4) . . ?
O4 C35 C33 115.2(3) . . ?
C31 C30 H30 120.6 . . ?
C29 C30 C31 118.9(2) . . ?
C29 C30 H30 120.6 . . ?
C22 C23 H23 120.0 . . ?
C22 C23 C24 120.0(2) . . ?
C24 C23 H23 120.0 . . ?
C25 C24 H24 120.1 . . ?
C23 C24 C25 119.8(2) . . ?
C23 C24 H24 120.1 . . ?
H43A C43 H43B 108.3 . . ?
C44 C43 H43A 109.9 . . ?
C44 C43 H43B 109.9 . . ?
C44 C43 C42 108.9(3) . . ?
C42 C43 H43A 109.9 . . ?
C42 C43 H43B 109.9 . . ?
N45 C44 C43 108.9(3) . . ?
N45 C44 H44A 109.9 . . ?
N45 C44 H44B 109.9 . . ?
C43 C44 H44A 109.9 . . ?
C43 C44 H44B 109.9 . . ?
H44A C44 H44B 108.3 . . ?
N41 C42 C43 109.3(3) . . ?
N41 C42 H42A 109.8 . . ?
N41 C42 H42B 109.8 . . ?
C43 C42 H42A 109.8 . . ?
C43 C42 H42B 109.8 . . ?
H42A C42 H42B 108.3 . . ?
C16 O5 H5A 109.5 . . ?
C7 O6 H6 109.5 . . ?
O6 C7 H7A 109.5 . . ?
O6 C7 H7B 109.5 . . ?
O6 C7 H7C 109.5 . . ?
H7A C7 H7B 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O5 C16 H16A 109.5 . . ?
O5 C16 H16B 109.5 . . ?
O5 C16 H16C 109.5 . . ?
H16A C16 H16B 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N45 C19 H19A 108.9 . . ?
N45 C19 H19B 108.9 . . ?
N45 C19 C18 113.3(17) . . ?
H19A C19 H19B 107.7 . . ?
C18 C19 H19A 108.9 . . ?
C18 C19 H19B 108.9 . . ?
C19 C18 H18A 106.2 . . ?
C19 C18 H18B 106.2 . . ?
C19 C18 C17 124(2) . . ?
H18A C18 H18B 106.4 . . ?
C17 C18 H18A 106.2 . . ?
C17 C18 H18B 106.2 . . ?
N41 C17 C18 126(3) . . ?
N41 C17 H17A 105.9 . . ?
N41 C17 H17B 105.9 . . ?
C18 C17 H17A 105.9 . . ?
C18 C17 H17B 105.9 . . ?
H17A C17 H17B 106.2 . . ?
C7A O6A H6A 109.5 . . ?
O6A C7A H7AA 109.5 . . ?
O6A C7A H7AB 109.5 . . ?
O6A C7A H7AC 109.5 . . ?
H7AA C7A H7AB 109.5 . . ?
H7AA C7A H7AC 109.5 . . ?
H7AB C7A H7AC 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cl18 C2 C3 C4 -174.74(16) . . . . ?
Cl39 C21 C22 C23 -175.21(17) . . . . ?
Cl19 C6 C5 C4 178.79(16) . . . . ?
Cl40 C25 C24 C23 179.66(18) . . . . ?
O17 C15 C14 C9 131.1(2) . . . . ?
N7 C1 C2 Cl18 -3.3(2) . . . . ?
N7 C1 C2 C3 179.37(17) . . . . ?
N7 C1 C6 Cl19 0.9(2) . . . . ?
N7 C1 C6 C5 179.30(18) . . . . ?
N7 C8 C9 C14 1.9(2) . . . . ?
N7 C8 C9 C10 -178.04(16) . . . . ?
N7 C8 C13 C12 177.95(17) . . . . ?
O16 C15 C14 C9 -49.6(3) . . . . ?
N26 C27 C32 C33 1.1(3) . . . . ?
N26 C27 C32 C31 -178.29(18) . . . . ?
N26 C27 C28 C29 177.64(18) . . . . ?
N26 C20 C21 Cl39 -2.9(3) . . . . ?
N26 C20 C21 C22 179.18(19) . . . . ?
N26 C20 C25 Cl40 -0.2(3) . . . . ?
N26 C20 C25 C24 179.48(19) . . . . ?
C1 N7 C8 C9 162.28(17) . . . . ?
C1 N7 C8 C13 -18.5(3) . . . . ?
C1 C2 C3 C4 2.6(3) . . . . ?
C1 C6 C5 C4 0.4(3) . . . . ?
C8 N7 C1 C2 -49.8(3) . . . . ?
C8 N7 C1 C6 135.15(18) . . . . ?
C8 C9 C14 C15 80.0(2) . . . . ?
C8 C9 C10 C11 -0.6(3) . . . . ?
C8 C13 C12 C11 0.7(3) . . . . ?
C2 C1 C6 Cl19 -174.58(13) . . . . ?
C2 C1 C6 C5 3.8(3) . . . . ?
C2 C3 C4 C5 1.9(3) . . . . ?
C6 C1 C2 Cl18 172.01(13) . . . . ?
C6 C1 C2 C3 -5.3(2) . . . . ?
C6 C5 C4 C3 -3.4(3) . . . . ?
C9 C8 C13 C12 -2.8(3) . . . . ?
C27 N26 C20 C21 -54.2(3) . . . . ?
C27 N26 C20 C25 130.4(2) . . . . ?
C27 C32 C33 C35 75.7(2) . . . . ?
C27 C32 C31 C30 0.2(3) . . . . ?
C27 C28 C29 C30 1.0(3) . . . . ?
C13 C8 C9 C14 -177.38(16) . . . . ?
C13 C8 C9 C10 2.7(3) . . . . ?
C13 C12 C11 C10 1.4(3) . . . . ?
C32 C27 C28 C29 -1.8(3) . . . . ?
C32 C33 C35 O1 80.8(3) . . . . ?
C32 C33 C35 O3 -99.2(3) . . . . ?
C32 C33 C35 O2 -13.6(4) . . . . ?
C32 C33 C35 O4 149.8(4) . . . . ?
C32 C31 C30 C29 -1.0(3) . . . . ?
N45 C19 C18 C17 -179(2) . . . . ?
C12 C11 C10 C9 -1.5(3) . . . . ?
C20 N26 C27 C32 166.80(18) . . . . ?
C20 N26 C27 C28 -12.6(3) . . . . ?
C20 C21 C22 C23 2.8(3) . . . . ?
C20 C25 C24 C23 0.0(3) . . . . ?
C21 C20 C25 Cl40 -175.89(14) . . . . ?
C21 C20 C25 C24 3.7(3) . . . . ?
C21 C22 C23 C24 1.3(3) . . . . ?
C28 C27 C32 C33 -179.50(17) . . . . ?
C28 C27 C32 C31 1.1(3) . . . . ?
C28 C29 C30 C31 0.4(3) . . . . ?
C14 C9 C10 C11 179.50(18) . . . . ?
C10 C9 C14 C15 -100.1(2) . . . . ?
C33 C32 C31 C30 -179.1(2) . . . . ?
C22 C23 C24 C25 -2.7(3) . . . . ?
C31 C32 C33 C35 -104.9(2) . . . . ?
C25 C20 C21 Cl39 172.80(14) . . . . ?
C25 C20 C21 C22 -5.2(3) . . . . ?
C44 C43 C42 N41 -178.6(3) . . . . ?
C42 C43 C44 N45 -175.2(2) . . . . ?
C19 C18 C17 N41 51(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
####################################################################### 
# 
# 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_twincr_twin2_hklf4
_database_code_depnum_ccdc_archive 'CCDC 2245277'
loop_
_audit_author_name
_audit_author_address
'Christopher Richardson'
;University of Wollongong
Australia
;
_audit_update_record             
;
2024-05-13 deposited with the CCDC.	2024-05-23 downloaded from the CCDC.
;
_audit_creation_date             2024-05-12
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C14 H10 Cl2 N O2), C3 H12 N2, C3 H8 O'
_chemical_formula_sum            'C34 H40 Cl4 N4 O5'
_chemical_formula_weight         726.50
_chemical_melting_point          ?
_chemical_oxdiff_formula         C35H40Cl4N3O5
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.4880(3)
_cell_length_b                   9.7666(3)
_cell_length_c                   18.9486(7)
_cell_angle_alpha                88.206(3)
_cell_angle_beta                 78.488(3)
_cell_angle_gamma                88.798(3)
_cell_volume                     1719.52(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    7646
_cell_measurement_temperature    100(1)
_cell_measurement_theta_max      78.5580
_cell_measurement_theta_min      4.8780
_shelx_estimated_absorpt_T_max   0.872
_shelx_estimated_absorpt_T_min   0.364
_exptl_absorpt_coefficient_mu    3.519
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.54346
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.49 (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.403
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             760
_exptl_crystal_recrystallization_method 'from isopropanol solution'
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0826
_diffrn_reflns_av_unetI/netI     0.0557
_diffrn_reflns_Laue_measured_fraction_full 0.971
_diffrn_reflns_Laue_measured_fraction_max 0.908
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            17521
_diffrn_reflns_point_group_measured_fraction_full 0.971
_diffrn_reflns_point_group_measured_fraction_max 0.908
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         78.525
_diffrn_reflns_theta_min         4.530
_diffrn_ambient_temperature      100(1)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.971
_diffrn_measured_fraction_theta_max 0.908
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     40.00  76.00   0.50    0.69    --  109.94-126.00-150.00   72
  2  ω     83.00 108.00   0.50    0.69    --  109.94-126.00-150.00   50
  3  ω     38.00  90.00   0.50    0.17    --   46.83-126.00 -30.00  104
  4  ω     42.00  81.00   0.50    0.17    --   46.83-110.00 -17.00   78
  5  ω     77.00 105.00   0.50    0.69    --  109.94 -95.00 120.00   56
  6  ω     38.00  69.00   0.50    0.69    --  109.94 -95.00 120.00   62
  7  ω     58.00 105.00   0.50    0.69    --  109.94 -95.00  30.00   94
  8  ω     40.00  89.00   0.50    0.69    --  109.94 -95.00-150.00   98
  9  ω    106.00 133.00   0.50    0.69    --  109.94 -88.00 104.02   54
 10  ω     38.00  76.00   0.50    0.69    --  109.94 -30.00  90.00   76
 11  ω     80.00 117.00   0.50    0.69    --  109.94 -30.00  90.00   74
 12  ω     37.00 126.00   0.50    0.69    --  109.94 -77.00 -30.00  178
 13  ω     41.00 131.00   0.50    0.69    --  109.94 -77.00 -90.00  180
 14  ω     48.00 123.00   0.50    0.69    --  109.94 -45.00 -30.00  150
 15  ω     36.00  81.00   0.50    0.17    --   46.83  38.00 -30.00   90
 16  ω    123.00 166.00   0.50    0.69    --  109.94  77.00 150.00   86
 17  ω    104.00 152.00   0.50    0.69    --  109.94 110.00  77.00   96
 18  ω    110.00 164.00   0.50    0.69    --  109.94  77.00  30.00  108
 19  ω     95.00 134.00   0.50    0.69    --  109.94 126.00-120.00   78
 20  ω    138.00 177.00   0.50    0.69    --  109.94 126.00-120.00   78
 21  ω    -37.00  23.00   0.50    0.17    --  -46.83  57.00-150.00  120
 22  ω   -104.00 -21.00   0.50    0.69    --  -91.75  15.00 -60.00  166
 23  ω    -60.00  24.00   0.50    0.17    --  -46.83  38.00 120.00  168
 24  ω    -50.00 -16.00   0.50    0.69    --  -91.75  15.00  60.00   68
 25  ω    -95.00 -68.00   0.50    0.69    --  -91.75  15.00  60.00   54
 26  ω   -131.00 -82.00   0.50    0.69    --  -91.75-110.00 -17.00   98
 27  ω   -150.00-123.00   0.50    0.69    --  -91.75 -77.00 120.00   54
 28  ω   -139.00-112.00   0.50    0.69    --  -91.75 -77.00  90.00   54
 29  ω   -142.00-115.00   0.50    0.69    --  -91.75 -77.00   0.00   54
 30  ω   -162.00-113.00   0.50    0.69    --  -91.75 -77.00-150.00   98
 31  ω   -115.00 -51.00   0.50    0.17    --  -46.83 -38.00 -60.00  128
 32  ω    -66.00  -9.00   0.50    0.17    --  -46.83 110.00  77.00  114
 33  ω    -81.00 -55.00   0.50    0.69    --  -91.75 110.00  77.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0584899000
_diffrn_orient_matrix_UB_12      -0.0100225000
_diffrn_orient_matrix_UB_13      0.0702391000
_diffrn_orient_matrix_UB_21      -0.1449609000
_diffrn_orient_matrix_UB_22      -0.0570700000
_diffrn_orient_matrix_UB_23      0.0403866000
_diffrn_orient_matrix_UB_31      0.0550375000
_diffrn_orient_matrix_UB_32      -0.1468126000
_diffrn_orient_matrix_UB_33      -0.0180249000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5646
_reflns_number_total             6716
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.49 (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.718
_refine_diff_density_min         -0.798
_refine_diff_density_rms         0.148
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     434
_refine_ls_number_reflns         6716
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0916
_refine_ls_R_factor_gt           0.0770
_refine_ls_restrained_S_all      1.083
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1668P)²+3.1219P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2267
_refine_ls_wR_factor_ref         0.2583
_refine_special_details          Twin
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H) groups, All N(H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2. Restrained distances
 N1A-H1A
 0.88 with sigma of 0.01
3. Others
 Sof(H1IA)=1-FVAR(1)
 Sof(H1I)=FVAR(1)
4.a Ternary CH refined with riding coordinates:
 C2I(H2I)
4.b Secondary CH2 refined with riding coordinates:
 C13A(H13A,H13B), C13B(H13C,H13D), C2P(H2PA,H2PB), C3P(H3PA,H3PB), C4P(H4PA,
 H4PB)
4.c Aromatic/amide H refined with riding coordinates:
 C3A(H3A), C4A(H4A), C5A(H5A), C8A(H8A), C9A(H9A), C10A(H10A), C11A(H11A),
 N1B(H1B), C3B(H3B), C4B(H4B), C5B(H5B), C8B(H8B), C9B(H9B), C10B(H10B),
 C11B(H11B)
4.d Idealised Me refined as rotating group:
 C1I(H1IB,H1IC,H1ID), C3I(H3IA,H3IB,H3IC), N1P(H1PA,H1PB,H1PC), N5P(H5PA,H5PB,
 H5PC)
4.e Idealised tetrahedral OH refined as rotating group:
 O1I(H1I), O1I(H1IA)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
H1A H 0.937(5) 0.276(4) 0.7474(11) 0.013(10) Uiso 1 1 d D . . . .
Cl1A Cl 1.11641(12) 0.44344(12) 0.76838(6) 0.0374(3) Uani 1 1 d . . . . .
O1A O 0.8085(3) 0.2288(3) 0.86010(16) 0.0319(7) Uani 1 1 d . . . . .
N1A N 0.9176(4) 0.2755(4) 0.70403(19) 0.0287(7) Uani 1 1 d D . . . .
C1A C 1.0173(4) 0.3495(4) 0.6546(2) 0.0272(8) Uani 1 1 d . . . . .
Cl2A Cl 0.93186(11) 0.22180(10) 0.54418(5) 0.0295(3) Uani 1 1 d . . . . .
O2A O 0.7795(3) 0.0157(3) 0.90634(16) 0.0312(6) Uani 1 1 d . . . . .
C2A C 1.1168(5) 0.4341(4) 0.6762(2) 0.0292(9) Uani 1 1 d . . . . .
C3A C 1.2171(5) 0.5107(4) 0.6284(3) 0.0353(10) Uani 1 1 d . . . . .
H3A H 1.282063 0.567152 0.645907 0.042 Uiso 1 1 calc R U . . .
C4A C 1.2218(5) 0.5045(4) 0.5557(3) 0.0348(10) Uani 1 1 d . . . . .
H4A H 1.286717 0.560009 0.522763 0.042 Uiso 1 1 calc R U . . .
C5A C 1.1304(4) 0.4160(4) 0.5307(2) 0.0288(8) Uani 1 1 d . . . . .
H5A H 1.135390 0.408594 0.480372 0.035 Uiso 1 1 calc R U . . .
C6A C 1.0317(5) 0.3382(4) 0.5795(2) 0.0302(9) Uani 1 1 d . . . . .
C7A C 0.7716(5) 0.2623(4) 0.7009(2) 0.0273(8) Uani 1 1 d . . . . .
C8A C 0.7001(5) 0.3558(4) 0.6619(2) 0.0301(9) Uani 1 1 d . . . . .
H8A H 0.750937 0.431912 0.637528 0.036 Uiso 1 1 calc R U . . .
C9A C 0.5579(5) 0.3397(5) 0.6584(2) 0.0322(9) Uani 1 1 d . . . . .
H9A H 0.512238 0.402765 0.630628 0.039 Uiso 1 1 calc R U . . .
C10A C 0.4807(5) 0.2302(5) 0.6956(2) 0.0330(9) Uani 1 1 d . . . . .
H10A H 0.382480 0.218176 0.693687 0.040 Uiso 1 1 calc R U . . .
C11A C 0.5505(5) 0.1394(4) 0.7355(2) 0.0308(9) Uani 1 1 d . . . . .
H11A H 0.498052 0.065587 0.761332 0.037 Uiso 1 1 calc R U . . .
C12A C 0.6946(5) 0.1528(4) 0.7390(2) 0.0278(8) Uani 1 1 d . . . . .
C13A C 0.7663(5) 0.0510(4) 0.7829(2) 0.0290(9) Uani 1 1 d . . . . .
H13A H 0.861486 0.024943 0.754084 0.035 Uiso 1 1 calc R U . . .
H13B H 0.707578 -0.032691 0.791714 0.035 Uiso 1 1 calc R U . . .
C14A C 0.7872(4) 0.1024(4) 0.8548(2) 0.0276(8) Uani 1 1 d . . . . .
Cl1B Cl 0.80477(11) 0.03914(10) 0.23991(5) 0.0309(3) Uani 1 1 d . . . . .
O1B O 0.5551(3) 0.2034(3) 0.14968(16) 0.0312(7) Uani 1 1 d . . . . .
N1B N 0.5494(4) 0.2103(3) 0.30356(18) 0.0262(7) Uani 1 1 d . . . . .
H1B H 0.602585 0.247594 0.264595 0.031 Uiso 1 1 calc R U . . .
C1B C 0.6193(4) 0.1464(4) 0.3536(2) 0.0253(8) Uani 1 1 d . . . . .
Cl2B Cl 0.45731(10) 0.29414(10) 0.46199(5) 0.0291(3) Uani 1 1 d . . . . .
O2B O 0.5022(3) 0.3793(3) 0.08167(15) 0.0287(6) Uani 1 1 d . . . . .
C2B C 0.7393(4) 0.0585(4) 0.3315(2) 0.0267(8) Uani 1 1 d . . . . .
C3B C 0.8100(4) -0.0098(4) 0.3797(2) 0.0281(8) Uani 1 1 d . . . . .
H3B H 0.889887 -0.068393 0.362523 0.034 Uiso 1 1 calc R U . . .
C4B C 0.7640(5) 0.0076(4) 0.4528(2) 0.0281(8) Uani 1 1 d . . . . .
H4B H 0.808224 -0.042845 0.486425 0.034 Uiso 1 1 calc R U . . .
C5B C 0.6532(5) 0.0990(4) 0.4765(2) 0.0275(8) Uani 1 1 d . . . . .
H5B H 0.623298 0.113405 0.526688 0.033 Uiso 1 1 calc R U . . .
C6B C 0.5848(4) 0.1702(4) 0.4281(2) 0.0258(8) Uani 1 1 d . . . . .
C7B C 0.3975(4) 0.2194(4) 0.3112(2) 0.0246(8) Uani 1 1 d . . . . .
C8B C 0.3053(4) 0.1377(4) 0.3601(2) 0.0251(8) Uani 1 1 d . . . . .
H8B H 0.344061 0.071431 0.389056 0.030 Uiso 1 1 calc R U . . .
C9B C 0.1573(5) 0.1512(4) 0.3674(2) 0.0269(8) Uani 1 1 d . . . . .
H9B H 0.095454 0.094360 0.401133 0.032 Uiso 1 1 calc R U . . .
C10B C 0.0994(5) 0.2478(4) 0.3254(2) 0.0279(8) Uani 1 1 d . . . . .
H10B H -0.001873 0.259547 0.331170 0.033 Uiso 1 1 calc R U . . .
C11B C 0.1918(5) 0.3270(4) 0.2749(2) 0.0287(8) Uani 1 1 d . . . . .
H11B H 0.152318 0.392009 0.245606 0.034 Uiso 1 1 calc R U . . .
C12B C 0.3394(5) 0.3138(4) 0.2662(2) 0.0254(8) Uani 1 1 d . . . . .
C13B C 0.4375(5) 0.3988(4) 0.2095(2) 0.0271(8) Uani 1 1 d . . . . .
H13C H 0.516624 0.433626 0.230623 0.033 Uiso 1 1 calc R U . . .
H13D H 0.382410 0.478920 0.195521 0.033 Uiso 1 1 calc R U . . .
C14B C 0.5021(4) 0.3202(4) 0.1419(2) 0.0240(8) Uani 1 1 d . . . . .
O1I O 1.0042(4) 0.1563(3) 0.07453(17) 0.0326(7) Uani 1 1 d . . . . .
H1I H 1.071350 0.110258 0.087035 0.049 Uiso 0.78(11) 1 calc R U P A 1
H1IA H 0.971914 0.100148 0.108020 0.049 Uiso 0.22(11) 1 calc R U P A 2
C1I C 0.8909(5) 0.3748(5) 0.0712(3) 0.0391(10) Uani 1 1 d . . . . .
H1IB H 0.913401 0.368686 0.018658 0.059 Uiso 1 1 calc R U . . .
H1IC H 0.893137 0.470795 0.084477 0.059 Uiso 1 1 calc R U . . .
H1ID H 0.794857 0.338195 0.089951 0.059 Uiso 1 1 calc R U . . .
C2I C 1.0006(5) 0.2927(4) 0.1030(2) 0.0326(9) Uani 1 1 d . . . . .
H2I H 0.967873 0.286362 0.156561 0.039 Uiso 1 1 calc R U . . .
C3I C 1.1475(5) 0.3547(5) 0.0858(3) 0.0388(10) Uani 1 1 d . . . . .
H3IA H 1.214939 0.296437 0.106645 0.058 Uiso 1 1 calc R U . . .
H3IB H 1.143185 0.446119 0.106026 0.058 Uiso 1 1 calc R U . . .
H3IC H 1.180311 0.361867 0.033384 0.058 Uiso 1 1 calc R U . . .
N1P N 0.7474(4) 0.0511(3) 0.05156(19) 0.0288(7) Uani 1 1 d . . . . .
H1PA H 0.749431 0.058074 0.003373 0.035 Uiso 1 1 calc R U . . .
H1PB H 0.833066 0.078411 0.060594 0.035 Uiso 1 1 calc R U . . .
H1PC H 0.675320 0.105289 0.075309 0.035 Uiso 1 1 calc R U . . .
C2P C 0.7221(5) -0.0938(4) 0.0768(2) 0.0299(9) Uani 1 1 d . . . . .
H2PA H 0.713571 -0.100444 0.129678 0.036 Uiso 1 1 calc R U . . .
H2PB H 0.805097 -0.151526 0.054428 0.036 Uiso 1 1 calc R U . . .
C3P C 0.5854(4) -0.1462(4) 0.0570(2) 0.0275(8) Uani 1 1 d . . . . .
H3PA H 0.503447 -0.084660 0.076301 0.033 Uiso 1 1 calc R U . . .
H3PB H 0.596619 -0.146310 0.003914 0.033 Uiso 1 1 calc R U . . .
C4P C 0.5550(5) -0.2903(4) 0.0878(2) 0.0283(8) Uani 1 1 d . . . . .
H4PA H 0.641671 -0.348653 0.072794 0.034 Uiso 1 1 calc R U . . .
H4PB H 0.534343 -0.287770 0.141074 0.034 Uiso 1 1 calc R U . . .
N5P N 0.4319(4) -0.3517(3) 0.06381(18) 0.0277(7) Uani 1 1 d . . . . .
H5PA H 0.443668 -0.341842 0.015081 0.033 Uiso 1 1 calc R U . . .
H5PB H 0.348900 -0.308798 0.085029 0.033 Uiso 1 1 calc R U . . .
H5PC H 0.427464 -0.442389 0.076560 0.033 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
Cl1A C2A 1.752(5) . ?
O1A C14A 1.265(5) . ?
N1A H1A 0.876(10) . ?
N1A C1A 1.389(5) . ?
N1A C7A 1.407(6) . ?
C1A C2A 1.396(6) . ?
C1A C6A 1.409(6) . ?
Cl2A C6A 1.727(5) . ?
O2A C14A 1.264(5) . ?
C2A C3A 1.389(6) . ?
C3A H3A 0.9500 . ?
C3A C4A 1.371(7) . ?
C4A H4A 0.9500 . ?
C4A C5A 1.395(7) . ?
C5A H5A 0.9500 . ?
C5A C6A 1.397(6) . ?
C7A C8A 1.404(6) . ?
C7A C12A 1.404(6) . ?
C8A H8A 0.9500 . ?
C8A C9A 1.377(6) . ?
C9A H9A 0.9500 . ?
C9A C10A 1.399(6) . ?
C10A H10A 0.9500 . ?
C10A C11A 1.389(6) . ?
C11A H11A 0.9500 . ?
C11A C12A 1.391(6) . ?
C12A C13A 1.513(6) . ?
C13A H13A 0.9900 . ?
C13A H13B 0.9900 . ?
C13A C14A 1.518(6) . ?
Cl1B C2B 1.738(4) . ?
O1B C14B 1.254(5) . ?
N1B H1B 0.8800 . ?
N1B C1B 1.388(5) . ?
N1B C7B 1.421(5) . ?
C1B C2B 1.414(6) . ?
C1B C6B 1.408(6) . ?
Cl2B C6B 1.737(4) . ?
O2B C14B 1.262(5) . ?
C2B C3B 1.384(6) . ?
C3B H3B 0.9500 . ?
C3B C4B 1.383(6) . ?
C4B H4B 0.9500 . ?
C4B C5B 1.378(6) . ?
C5B H5B 0.9500 . ?
C5B C6B 1.388(6) . ?
C7B C8B 1.386(6) . ?
C7B C12B 1.414(5) . ?
C8B H8B 0.9500 . ?
C8B C9B 1.388(6) . ?
C9B H9B 0.9500 . ?
C9B C10B 1.390(6) . ?
C10B H10B 0.9500 . ?
C10B C11B 1.389(6) . ?
C11B H11B 0.9500 . ?
C11B C12B 1.381(6) . ?
C12B C13B 1.512(5) . ?
C13B H13C 0.9900 . ?
C13B H13D 0.9900 . ?
C13B C14B 1.527(5) . ?
O1I H1I 0.8400 . ?
O1I H1IA 0.8400 . ?
O1I C2I 1.450(5) . ?
C1I H1IB 0.9800 . ?
C1I H1IC 0.9800 . ?
C1I H1ID 0.9800 . ?
C1I C2I 1.508(7) . ?
C2I H2I 1.0000 . ?
C2I C3I 1.503(6) . ?
C3I H3IA 0.9800 . ?
C3I H3IB 0.9800 . ?
C3I H3IC 0.9800 . ?
N1P H1PA 0.9100 . ?
N1P H1PB 0.9100 . ?
N1P H1PC 0.9100 . ?
N1P C2P 1.488(5) . ?
C2P H2PA 0.9900 . ?
C2P H2PB 0.9900 . ?
C2P C3P 1.523(6) . ?
C3P H3PA 0.9900 . ?
C3P H3PB 0.9900 . ?
C3P C4P 1.517(5) . ?
C4P H4PA 0.9900 . ?
C4P H4PB 0.9900 . ?
C4P N5P 1.479(6) . ?
N5P H5PA 0.9100 . ?
N5P H5PB 0.9100 . ?
N5P H5PC 0.9100 . ?

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
C1A N1A H1A 112(3) . . ?
C1A N1A C7A 125.0(3) . . ?
C7A N1A H1A 116(3) . . ?
N1A C1A C2A 121.8(4) . . ?
N1A C1A C6A 122.8(4) . . ?
C2A C1A C6A 115.3(4) . . ?
C1A C2A Cl1A 118.4(3) . . ?
C3A C2A Cl1A 118.1(3) . . ?
C3A C2A C1A 123.5(4) . . ?
C2A C3A H3A 120.1 . . ?
C4A C3A C2A 119.7(4) . . ?
C4A C3A H3A 120.1 . . ?
C3A C4A H4A 120.3 . . ?
C3A C4A C5A 119.4(4) . . ?
C5A C4A H4A 120.3 . . ?
C4A C5A H5A 120.0 . . ?
C4A C5A C6A 120.1(4) . . ?
C6A C5A H5A 120.0 . . ?
C1A C6A Cl2A 120.9(3) . . ?
C5A C6A C1A 121.8(4) . . ?
C5A C6A Cl2A 117.2(3) . . ?
C8A C7A N1A 122.2(4) . . ?
C12A C7A N1A 118.7(4) . . ?
C12A C7A C8A 119.1(4) . . ?
C7A C8A H8A 119.3 . . ?
C9A C8A C7A 121.4(4) . . ?
C9A C8A H8A 119.3 . . ?
C8A C9A H9A 120.1 . . ?
C8A C9A C10A 119.9(4) . . ?
C10A C9A H9A 120.1 . . ?
C9A C10A H10A 120.6 . . ?
C11A C10A C9A 118.7(4) . . ?
C11A C10A H10A 120.6 . . ?
C10A C11A H11A 118.9 . . ?
C10A C11A C12A 122.2(4) . . ?
C12A C11A H11A 118.9 . . ?
C7A C12A C13A 121.0(4) . . ?
C11A C12A C7A 118.7(4) . . ?
C11A C12A C13A 120.4(4) . . ?
C12A C13A H13A 108.6 . . ?
C12A C13A H13B 108.6 . . ?
C12A C13A C14A 114.7(3) . . ?
H13A C13A H13B 107.6 . . ?
C14A C13A H13A 108.6 . . ?
C14A C13A H13B 108.6 . . ?
O1A C14A C13A 118.5(4) . . ?
O2A C14A O1A 124.0(4) . . ?
O2A C14A C13A 117.4(4) . . ?
C1B N1B H1B 117.9 . . ?
C1B N1B C7B 124.2(3) . . ?
C7B N1B H1B 117.9 . . ?
N1B C1B C2B 120.9(4) . . ?
N1B C1B C6B 123.8(4) . . ?
C6B C1B C2B 115.1(4) . . ?
C1B C2B Cl1B 118.8(3) . . ?
C3B C2B Cl1B 118.3(3) . . ?
C3B C2B C1B 122.8(4) . . ?
C2B C3B H3B 120.1 . . ?
C4B C3B C2B 119.7(4) . . ?
C4B C3B H3B 120.1 . . ?
C3B C4B H4B 120.3 . . ?
C5B C4B C3B 119.3(4) . . ?
C5B C4B H4B 120.3 . . ?
C4B C5B H5B 119.6 . . ?
C4B C5B C6B 120.9(4) . . ?
C6B C5B H5B 119.6 . . ?
C1B C6B Cl2B 120.6(3) . . ?
C5B C6B C1B 121.7(4) . . ?
C5B C6B Cl2B 117.7(3) . . ?
C8B C7B N1B 122.3(3) . . ?
C8B C7B C12B 119.3(4) . . ?
C12B C7B N1B 118.4(3) . . ?
C7B C8B H8B 119.5 . . ?
C7B C8B C9B 120.9(4) . . ?
C9B C8B H8B 119.5 . . ?
C8B C9B H9B 120.0 . . ?
C8B C9B C10B 120.1(4) . . ?
C10B C9B H9B 120.0 . . ?
C9B C10B H10B 120.5 . . ?
C11B C10B C9B 119.0(4) . . ?
C11B C10B H10B 120.5 . . ?
C10B C11B H11B 119.1 . . ?
C12B C11B C10B 121.8(4) . . ?
C12B C11B H11B 119.1 . . ?
C7B C12B C13B 120.4(4) . . ?
C11B C12B C7B 118.9(4) . . ?
C11B C12B C13B 120.7(4) . . ?
C12B C13B H13C 108.8 . . ?
C12B C13B H13D 108.8 . . ?
C12B C13B C14B 113.7(3) . . ?
H13C C13B H13D 107.7 . . ?
C14B C13B H13C 108.8 . . ?
C14B C13B H13D 108.8 . . ?
O1B C14B O2B 124.2(4) . . ?
O1B C14B C13B 118.2(3) . . ?
O2B C14B C13B 117.5(3) . . ?
C2I O1I H1I 109.5 . . ?
C2I O1I H1IA 109.5 . . ?
H1IB C1I H1IC 109.5 . . ?
H1IB C1I H1ID 109.5 . . ?
H1IC C1I H1ID 109.5 . . ?
C2I C1I H1IB 109.5 . . ?
C2I C1I H1IC 109.5 . . ?
C2I C1I H1ID 109.5 . . ?
O1I C2I C1I 106.7(4) . . ?
O1I C2I H2I 108.9 . . ?
O1I C2I C3I 110.7(4) . . ?
C1I C2I H2I 108.9 . . ?
C3I C2I C1I 112.8(4) . . ?
C3I C2I H2I 108.9 . . ?
C2I C3I H3IA 109.5 . . ?
C2I C3I H3IB 109.5 . . ?
C2I C3I H3IC 109.5 . . ?
H3IA C3I H3IB 109.5 . . ?
H3IA C3I H3IC 109.5 . . ?
H3IB C3I H3IC 109.5 . . ?
H1PA N1P H1PB 109.5 . . ?
H1PA N1P H1PC 109.5 . . ?
H1PB N1P H1PC 109.5 . . ?
C2P N1P H1PA 109.5 . . ?
C2P N1P H1PB 109.5 . . ?
C2P N1P H1PC 109.5 . . ?
N1P C2P H2PA 109.5 . . ?
N1P C2P H2PB 109.5 . . ?
N1P C2P C3P 110.7(3) . . ?
H2PA C2P H2PB 108.1 . . ?
C3P C2P H2PA 109.5 . . ?
C3P C2P H2PB 109.5 . . ?
C2P C3P H3PA 109.6 . . ?
C2P C3P H3PB 109.6 . . ?
H3PA C3P H3PB 108.2 . . ?
C4P C3P C2P 110.1(3) . . ?
C4P C3P H3PA 109.6 . . ?
C4P C3P H3PB 109.6 . . ?
C3P C4P H4PA 109.1 . . ?
C3P C4P H4PB 109.1 . . ?
H4PA C4P H4PB 107.9 . . ?
N5P C4P C3P 112.4(3) . . ?
N5P C4P H4PA 109.1 . . ?
N5P C4P H4PB 109.1 . . ?
C4P N5P H5PA 109.5 . . ?
C4P N5P H5PB 109.5 . . ?
C4P N5P H5PC 109.5 . . ?
H5PA N5P H5PB 109.5 . . ?
H5PA N5P H5PC 109.5 . . ?
H5PB N5P H5PC 109.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O1I H1I O2A 0.84 1.88 2.698(4) 165.6 2_756 yes
N1P H1PA O2A 0.91 1.86 2.740(5) 161.3 1_554 yes
N1P H1PB O1I 0.91 1.88 2.782(5) 172.8 . yes
N1P H1PC O1B 0.91 1.90 2.776(5) 161.5 . yes
N5P H5PA O2B 0.91 1.85 2.723(5) 160.4 2_655 yes
N5P H5PB O1A 0.91 1.82 2.721(5) 171.5 2_656 yes
N5P H5PC O2B 0.91 1.87 2.724(4) 154.7 1_545 yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cl1A C2A C3A C4A 179.1(3) . . . . ?
N1A C1A C2A Cl1A 1.2(5) . . . . ?
N1A C1A C2A C3A -179.3(4) . . . . ?
N1A C1A C6A Cl2A -4.1(6) . . . . ?
N1A C1A C6A C5A 178.5(4) . . . . ?
N1A C7A C8A C9A 178.8(4) . . . . ?
N1A C7A C12A C11A -179.7(4) . . . . ?
N1A C7A C12A C13A 0.2(6) . . . . ?
C1A N1A C7A C8A -21.2(6) . . . . ?
C1A N1A C7A C12A 159.8(4) . . . . ?
C1A C2A C3A C4A -0.4(7) . . . . ?
C2A C1A C6A Cl2A 172.0(3) . . . . ?
C2A C1A C6A C5A -5.5(6) . . . . ?
C2A C3A C4A C5A -3.2(6) . . . . ?
C3A C4A C5A C6A 2.3(6) . . . . ?
C4A C5A C6A C1A 2.3(6) . . . . ?
C4A C5A C6A Cl2A -175.3(3) . . . . ?
C6A C1A C2A Cl1A -174.9(3) . . . . ?
C6A C1A C2A C3A 4.6(6) . . . . ?
C7A N1A C1A C2A 137.0(4) . . . . ?
C7A N1A C1A C6A -47.3(6) . . . . ?
C7A C8A C9A C10A 1.7(7) . . . . ?
C7A C12A C13A C14A 77.0(5) . . . . ?
C8A C7A C12A C11A 1.3(6) . . . . ?
C8A C7A C12A C13A -178.8(4) . . . . ?
C8A C9A C10A C11A -0.2(7) . . . . ?
C9A C10A C11A C12A -0.7(7) . . . . ?
C10A C11A C12A C7A 0.2(6) . . . . ?
C10A C11A C12A C13A -179.7(4) . . . . ?
C11A C12A C13A C14A -103.1(5) . . . . ?
C12A C7A C8A C9A -2.3(6) . . . . ?
C12A C13A C14A O1A -31.7(5) . . . . ?
C12A C13A C14A O2A 147.0(4) . . . . ?
Cl1B C2B C3B C4B 177.5(3) . . . . ?
N1B C1B C2B Cl1B 3.7(5) . . . . ?
N1B C1B C2B C3B -178.4(4) . . . . ?
N1B C1B C6B Cl2B -4.8(6) . . . . ?
N1B C1B C6B C5B 176.9(4) . . . . ?
N1B C7B C8B C9B 178.5(4) . . . . ?
N1B C7B C12B C11B -177.7(4) . . . . ?
N1B C7B C12B C13B 2.3(6) . . . . ?
C1B N1B C7B C8B -16.1(6) . . . . ?
C1B N1B C7B C12B 165.0(4) . . . . ?
C1B C2B C3B C4B -0.4(6) . . . . ?
C2B C1B C6B Cl2B 170.8(3) . . . . ?
C2B C1B C6B C5B -7.5(6) . . . . ?
C2B C3B C4B C5B -3.7(6) . . . . ?
C3B C4B C5B C6B 2.0(6) . . . . ?
C4B C5B C6B C1B 3.9(6) . . . . ?
C4B C5B C6B Cl2B -174.5(3) . . . . ?
C6B C1B C2B Cl1B -172.1(3) . . . . ?
C6B C1B C2B C3B 5.8(6) . . . . ?
C7B N1B C1B C2B 135.7(4) . . . . ?
C7B N1B C1B C6B -48.9(6) . . . . ?
C7B C8B C9B C10B -0.1(6) . . . . ?
C7B C12B C13B C14B 78.1(5) . . . . ?
C8B C7B C12B C11B 3.4(6) . . . . ?
C8B C7B C12B C13B -176.6(4) . . . . ?
C8B C9B C10B C11B 1.9(6) . . . . ?
C9B C10B C11B C12B -1.1(6) . . . . ?
C10B C11B C12B C7B -1.6(6) . . . . ?
C10B C11B C12B C13B 178.4(4) . . . . ?
C11B C12B C13B C14B -101.9(4) . . . . ?
C12B C7B C8B C9B -2.6(6) . . . . ?
C12B C13B C14B O1B -46.8(5) . . . . ?
C12B C13B C14B O2B 135.3(4) . . . . ?
N1P C2P C3P C4P -175.8(3) . . . . ?
C2P C3P C4P N5P -174.0(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 4.034
_oxdiff_exptl_absorpt_empirical_full_min 0.516
_oxdiff_twin_integration_method  simultaneous
_oxdiff_twin_items               4
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
_oxdiff_twin_reflns_isolated
_oxdiff_twin_reflns_overlapped
_twin_individual_twin_lattice_type
_twin_individual_twin_matrix_11
_twin_individual_twin_matrix_12
_twin_individual_twin_matrix_13
_twin_individual_twin_matrix_21
_twin_individual_twin_matrix_22
_twin_individual_twin_matrix_23
_twin_individual_twin_matrix_31
_twin_individual_twin_matrix_32
_twin_individual_twin_matrix_33
1 0.2879 13641 4642 ref 1.0000 0.0000 0.0000 0.0000 1.0000 0.0000 0.0000 0.0000
1.0000
2 0.4812 13950 3834 nmt 0.9970 -0.0380 0.0090 0.0029 -0.9991 0.0011 0.8279
-0.0207 -0.9963
3 0.1097 16351 2623 nmt 1.0118 0.0042 -0.0356 0.0408 -0.9995 0.0336 0.6651
-0.1228 -1.0073
4 0.1211 15491 3316 nmt 0.9839 -0.0040 0.0353 0.0197 0.9997 -0.0337 -0.1409
0.1228 1.0073

_twin_special_details            
;
Component 2 rotated by -179.8527° 
around [0.92 0.00 0.38] (reciprocal) or [1.00 -0.02 0.00] (direct)
Component 3 rotated by -176.2958° 
around [0.95 0.02 0.31] (reciprocal) or [1.00 0.00 -0.02] (direct)
Component 4 rotated by 5.4397° 
around [0.62 0.69 0.36] (reciprocal) or [0.68 0.73 0.02] (direct)
;
####################################################################### 
# 
# 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_exp_375_cr_auto
_database_code_depnum_ccdc_archive 'CCDC 2210150'
loop_
_audit_author_name
_audit_author_address
'Christopher Richardson'
;University of Wollongong
Australia
;
_audit_update_record             
;
2024-05-13 deposited with the CCDC.	2024-05-23 downloaded from the CCDC.
;
_audit_creation_date             2024-05-11
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         
'2(C14 H10 Cl2 N O2), C3 H12 N2, 2(C2 H6 O1 S1)'
_chemical_formula_sum            'C35 H44 Cl4 N4 O6 S2'
_chemical_formula_weight         822.66
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           56
_space_group_name_H-M_alt        'P c c n'
_space_group_name_Hall           '-P 2ab 2ac'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y+1/2, z'
'-x, y+1/2, -z+1/2'
'x+1/2, -y, -z+1/2'
'-x, -y, -z'
'x-1/2, y-1/2, -z'
'x, -y-1/2, z-1/2'
'-x-1/2, y, z-1/2'

_cell_length_a                   9.6066(5)
_cell_length_b                   43.035(2)
_cell_length_c                   9.7812(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4043.7(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    10306
_cell_measurement_temperature    294(1)
_cell_measurement_theta_max      24.9700
_cell_measurement_theta_min      1.9140
_shelx_estimated_absorpt_T_max   0.978
_shelx_estimated_absorpt_T_min   0.806
_exptl_absorpt_coefficient_mu    0.443
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88677
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.123a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.351
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       rod
_exptl_crystal_F_000             1720
_exptl_crystal_recrystallization_method dimethylsulfoxide
_exptl_crystal_size_max          0.51
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0430
_diffrn_reflns_av_unetI/netI     0.0407
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       59
_diffrn_reflns_limit_k_min       -60
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            43370
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.972
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.387
_diffrn_reflns_theta_min         2.552
_diffrn_ambient_temperature      294.0(10)
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -74.00 110.00   0.50   35.00    --   20.00  54.00 148.12  368
  2  ω    -74.00 110.00   0.50   35.00    --   20.00  54.00  88.67  368
  3  ω    -74.00 110.00   0.50   35.00    --   20.00  54.00-149.63  368
  4  ω    -74.00  38.00   0.50   35.00    --   20.00  54.00 -30.84  224
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini II'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3840
_reflns_number_total             5935
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.894
_refine_diff_density_min         -0.364
_refine_diff_density_rms         0.062
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.045
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     273
_refine_ls_number_reflns         5935
_refine_ls_number_restraints     79
_refine_ls_R_factor_all          0.1096
_refine_ls_R_factor_gt           0.0665
_refine_ls_restrained_S_all      1.066
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0785P)²+3.4967P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1711
_refine_ls_wR_factor_ref         0.1910
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Restrained distances
 N1-H1
 0.85 with sigma of 0.02
 S1B-C2B = S1A-C2A = S1B-C1B = S1A-C1A
 1.75 with sigma of 0.02
 S1B-O1B
 1.5 with sigma of 0.02
 S1A-O1A
 1.5 with sigma of 0.01
3. Uiso/Uaniso restraints and constraints
S1A \\sim O1A \\sim C1A \\sim C2A: within 2A with sigma of 0.01 and sigma for
terminal atoms of 0.02 within 2A
S1B \\sim O1B \\sim C1B \\sim C2B: within 2A with sigma of 0.01 and sigma for
terminal atoms of 0.02 within 2A
4. Rigid body (RIGU) restrains
 S1B, O1B, C1B, C2B
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 S1A, O1A, C1A, C2A
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
5. Others
 Sof(S1B)=Sof(O1B)=Sof(C1B)=Sof(H1BA)=Sof(H1BB)=Sof(H1BC)=Sof(C2B)=Sof(H2BA)=
 Sof(H2BB)=Sof(H2BC)=1-FVAR(1)
 Sof(S1A)=Sof(O1A)=Sof(C1A)=Sof(H1AA)=Sof(H1AB)=Sof(H1AC)=Sof(C2A)=Sof(H2AA)=
 Sof(H2AB)=Sof(H2AC)=FVAR(1)
 Fixed Sof: H3SA(0.5) H3SB(0.5)
6.a Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C2S(H2SA,H2SB), C3S(H3SA,H3SB)
6.b Me refined with riding coordinates:
 C1A(H1AA,H1AB,H1AC), C2A(H2AA,H2AB,H2AC), C1B(H1BA,H1BB,H1BC), C2B(H2BA,H2BB,
 H2BC)
6.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C4(H4), C5(H5), C8(H8), C9(H9), C10(H10), C11(H11)
6.d Idealised Me refined as rotating group:
 N1S(H1SA,H1SB,H1SC)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.30152(8) 0.61362(2) 0.48161(10) 0.0609(3) Uani 1 1 d . . . . .
Cl2 Cl 0.55061(7) 0.51782(2) 0.21497(7) 0.04588(19) Uani 1 1 d . . . . .
O1 O 0.5440(3) 0.65273(5) 0.2725(2) 0.0614(6) Uani 1 1 d . . . . .
O2 O 0.6506(4) 0.67895(5) 0.1114(3) 0.0885(10) Uani 1 1 d . . . . .
N1 N 0.5159(2) 0.58632(5) 0.2953(2) 0.0398(5) Uani 1 1 d D . . . .
H1 H 0.487(3) 0.6049(5) 0.297(3) 0.050(9) Uiso 1 1 d D . . . .
C1 C 0.4325(3) 0.56480(6) 0.3630(2) 0.0339(5) Uani 1 1 d . . . . .
C2 C 0.3269(3) 0.57414(6) 0.4529(3) 0.0401(6) Uani 1 1 d . . . . .
C3 C 0.2412(3) 0.55336(8) 0.5208(3) 0.0492(7) Uani 1 1 d . . . . .
H3 H 0.172589 0.560565 0.579959 0.059 Uiso 1 1 calc R U . . .
C4 C 0.2585(3) 0.52188(7) 0.5000(3) 0.0501(7) Uani 1 1 d . . . . .
H4 H 0.203635 0.507705 0.547467 0.060 Uiso 1 1 calc R U . . .
C5 C 0.3577(3) 0.51152(6) 0.4085(3) 0.0438(6) Uani 1 1 d . . . . .
H5 H 0.368968 0.490329 0.393584 0.053 Uiso 1 1 calc R U . . .
C6 C 0.4398(3) 0.53249(6) 0.3391(3) 0.0351(5) Uani 1 1 d . . . . .
C7 C 0.6628(3) 0.58409(5) 0.2834(3) 0.0344(5) Uani 1 1 d . . . . .
C8 C 0.7409(3) 0.56498(6) 0.3681(3) 0.0393(6) Uani 1 1 d . . . . .
H8 H 0.696803 0.553385 0.435588 0.047 Uiso 1 1 calc R U . . .
C9 C 0.8835(3) 0.56304(7) 0.3529(3) 0.0484(7) Uani 1 1 d . . . . .
H9 H 0.935083 0.549977 0.409185 0.058 Uiso 1 1 calc R U . . .
C10 C 0.9491(3) 0.58049(8) 0.2541(3) 0.0548(8) Uani 1 1 d . . . . .
H10 H 1.045030 0.579134 0.242776 0.066 Uiso 1 1 calc R U . . .
C11 C 0.8717(3) 0.60002(7) 0.1721(3) 0.0509(7) Uani 1 1 d . . . . .
H11 H 0.916931 0.612055 0.106803 0.061 Uiso 1 1 calc R U . . .
C12 C 0.7285(3) 0.60216(6) 0.1845(3) 0.0384(6) Uani 1 1 d . . . . .
C13 C 0.6472(4) 0.62387(6) 0.0923(3) 0.0481(7) Uani 1 1 d . . . . .
H13A H 0.701653 0.628261 0.011043 0.058 Uiso 1 1 calc R U . . .
H13B H 0.561867 0.613707 0.063665 0.058 Uiso 1 1 calc R U . . .
C14 C 0.6116(3) 0.65409(6) 0.1631(3) 0.0486(7) Uani 1 1 d . . . . .
S1A S 0.3514(4) 0.68994(8) 0.6751(5) 0.141(2) Uani 0.472(5) 1 d D U P A 1
O1A O 0.455(2) 0.7173(4) 0.6666(14) 0.096(3) Uani 0.472(5) 1 d D U P A 1
C1A C 0.412(2) 0.6655(4) 0.798(2) 0.175(6) Uani 0.472(5) 1 d D U P A 1
H1AA H 0.350008 0.648089 0.806142 0.262 Uiso 0.472(5) 1 calc R U P A 1
H1AB H 0.502947 0.658286 0.772792 0.262 Uiso 0.472(5) 1 calc R U P A 1
H1AC H 0.416750 0.676320 0.883357 0.262 Uiso 0.472(5) 1 calc R U P A 1
C2A C 0.2332(19) 0.7053(5) 0.8078(19) 0.167(6) Uani 0.472(5) 1 d D U P A 1
H2AA H 0.160563 0.690520 0.825244 0.251 Uiso 0.472(5) 1 calc R U P A 1
H2AB H 0.284607 0.708980 0.890423 0.251 Uiso 0.472(5) 1 calc R U P A 1
H2AC H 0.192856 0.724487 0.776789 0.251 Uiso 0.472(5) 1 calc R U P A 1
S1B S 0.3785(4) 0.70773(7) 0.7659(3) 0.1183(14) Uani 0.528(5) 1 d D U P A 2
O1B O 0.440(2) 0.7177(5) 0.6268(16) 0.151(6) Uani 0.528(5) 1 d D U P A 2
C1B C 0.4635(16) 0.6721(3) 0.808(2) 0.146(5) Uani 0.528(5) 1 d D U P A 2
H1BA H 0.429364 0.664648 0.894029 0.219 Uiso 0.528(5) 1 calc R U P A 2
H1BB H 0.444920 0.656995 0.738079 0.219 Uiso 0.528(5) 1 calc R U P A 2
H1BC H 0.562078 0.675560 0.814074 0.219 Uiso 0.528(5) 1 calc R U P A 2
C2B C 0.2012(15) 0.7053(5) 0.705(2) 0.198(6) Uani 0.528(5) 1 d D U P A 2
H2BA H 0.141400 0.699075 0.778801 0.296 Uiso 0.528(5) 1 calc R U P A 2
H2BB H 0.172315 0.725225 0.671432 0.296 Uiso 0.528(5) 1 calc R U P A 2
H2BC H 0.195734 0.690264 0.632728 0.296 Uiso 0.528(5) 1 calc R U P A 2
N1S N 0.8625(3) 0.69814(6) -0.0535(3) 0.0554(7) Uani 1 1 d . . . . .
H1SA H 0.898143 0.683988 -0.109929 0.066 Uiso 1 1 calc R U . . .
H1SB H 0.793077 0.689731 -0.006047 0.066 Uiso 1 1 calc R U . . .
H1SC H 0.928346 0.704694 0.003643 0.066 Uiso 1 1 calc R U . . .
C2S C 0.8095(4) 0.72474(7) -0.1338(3) 0.0557(8) Uani 1 1 d . . . . .
H2SA H 0.737755 0.717491 -0.195912 0.067 Uiso 1 1 calc R U . . .
H2SB H 0.884651 0.733299 -0.188219 0.067 Uiso 1 1 calc R U . . .
C3S C 0.750000 0.750000 -0.0435(4) 0.0537(11) Uani 1 2 d S T P . .
H3SA H 0.822478 0.758500 0.014544 0.064 Uiso 0.5 1 calc R U P . .
H3SB H 0.677523 0.741499 0.014545 0.064 Uiso 0.5 1 calc R U P . .


_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 C2 1.739(3) . ?
Cl2 C6 1.734(3) . ?
O1 C14 1.254(4) . ?
O2 C14 1.241(3) . ?
N1 H1 0.847(17) . ?
N1 C1 1.392(3) . ?
N1 C7 1.420(3) . ?
C1 C2 1.401(4) . ?
C1 C6 1.412(3) . ?
C2 C3 1.385(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.380(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.382(4) . ?
C5 H5 0.9300 . ?
C5 C6 1.378(4) . ?
C7 C8 1.387(4) . ?
C7 C12 1.392(4) . ?
C8 H8 0.9300 . ?
C8 C9 1.381(4) . ?
C9 H9 0.9300 . ?
C9 C10 1.376(4) . ?
C10 H10 0.9300 . ?
C10 C11 1.379(5) . ?
C11 H11 0.9300 . ?
C11 C12 1.384(4) . ?
C12 C13 1.516(4) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C13 C14 1.513(4) . ?
S1A O1A 1.545(9) . ?
S1A C1A 1.697(17) . ?
S1A C2A 1.848(12) . ?
C1A H1AA 0.9600 . ?
C1A H1AB 0.9600 . ?
C1A H1AC 0.9600 . ?
C2A H2AA 0.9600 . ?
C2A H2AB 0.9600 . ?
C2A H2AC 0.9600 . ?
S1B O1B 1.545(13) . ?
S1B C1B 1.784(14) . ?
S1B C2B 1.807(14) . ?
C1B H1BA 0.9600 . ?
C1B H1BB 0.9600 . ?
C1B H1BC 0.9600 . ?
C2B H2BA 0.9600 . ?
C2B H2BB 0.9600 . ?
C2B H2BC 0.9600 . ?
N1S H1SA 0.8900 . ?
N1S H1SB 0.8900 . ?
N1S H1SC 0.8900 . ?
N1S C2S 1.479(4) . ?
C2S H2SA 0.9700 . ?
C2S H2SB 0.9700 . ?
C2S C3S 1.513(4) . ?
C3S H3SA 0.9700 . ?
C3S H3SB 0.9700 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 H1 116(2) . . ?
C1 N1 C7 124.5(2) . . ?
C7 N1 H1 113(2) . . ?
N1 C1 C2 121.6(2) . . ?
N1 C1 C6 123.2(2) . . ?
C2 C1 C6 115.0(2) . . ?
C1 C2 Cl1 118.9(2) . . ?
C3 C2 Cl1 118.0(2) . . ?
C3 C2 C1 123.1(3) . . ?
C2 C3 H3 120.3 . . ?
C4 C3 C2 119.4(3) . . ?
C4 C3 H3 120.3 . . ?
C3 C4 H4 120.2 . . ?
C3 C4 C5 119.7(3) . . ?
C5 C4 H4 120.2 . . ?
C4 C5 H5 119.9 . . ?
C6 C5 C4 120.2(3) . . ?
C6 C5 H5 119.9 . . ?
C1 C6 Cl2 120.36(19) . . ?
C5 C6 Cl2 117.3(2) . . ?
C5 C6 C1 122.3(3) . . ?
C8 C7 N1 121.9(2) . . ?
C8 C7 C12 120.0(2) . . ?
C12 C7 N1 118.0(2) . . ?
C7 C8 H8 119.7 . . ?
C9 C8 C7 120.5(3) . . ?
C9 C8 H8 119.7 . . ?
C8 C9 H9 120.1 . . ?
C10 C9 C8 119.8(3) . . ?
C10 C9 H9 120.1 . . ?
C9 C10 H10 120.2 . . ?
C9 C10 C11 119.6(3) . . ?
C11 C10 H10 120.2 . . ?
C10 C11 H11 119.2 . . ?
C10 C11 C12 121.7(3) . . ?
C12 C11 H11 119.2 . . ?
C7 C12 C13 121.6(3) . . ?
C11 C12 C7 118.3(3) . . ?
C11 C12 C13 120.1(3) . . ?
C12 C13 H13A 109.2 . . ?
C12 C13 H13B 109.2 . . ?
H13A C13 H13B 107.9 . . ?
C14 C13 C12 112.0(2) . . ?
C14 C13 H13A 109.2 . . ?
C14 C13 H13B 109.2 . . ?
O1 C14 C13 117.9(3) . . ?
O2 C14 O1 123.0(3) . . ?
O2 C14 C13 119.1(3) . . ?
O1A S1A C1A 106.8(10) . . ?
O1A S1A C2A 99.3(10) . . ?
C1A S1A C2A 86.3(11) . . ?
S1A C1A H1AA 109.5 . . ?
S1A C1A H1AB 109.5 . . ?
S1A C1A H1AC 109.5 . . ?
H1AA C1A H1AB 109.5 . . ?
H1AA C1A H1AC 109.5 . . ?
H1AB C1A H1AC 109.5 . . ?
S1A C2A H2AA 109.5 . . ?
S1A C2A H2AB 109.5 . . ?
S1A C2A H2AC 109.5 . . ?
H2AA C2A H2AB 109.5 . . ?
H2AA C2A H2AC 109.5 . . ?
H2AB C2A H2AC 109.5 . . ?
O1B S1B C1B 105.5(12) . . ?
O1B S1B C2B 95.1(11) . . ?
C1B S1B C2B 117.2(9) . . ?
S1B C1B H1BA 109.5 . . ?
S1B C1B H1BB 109.5 . . ?
S1B C1B H1BC 109.5 . . ?
H1BA C1B H1BB 109.5 . . ?
H1BA C1B H1BC 109.5 . . ?
H1BB C1B H1BC 109.5 . . ?
S1B C2B H2BA 109.5 . . ?
S1B C2B H2BB 109.5 . . ?
S1B C2B H2BC 109.5 . . ?
H2BA C2B H2BB 109.5 . . ?
H2BA C2B H2BC 109.5 . . ?
H2BB C2B H2BC 109.5 . . ?
H1SA N1S H1SB 109.5 . . ?
H1SA N1S H1SC 109.5 . . ?
H1SB N1S H1SC 109.5 . . ?
C2S N1S H1SA 109.5 . . ?
C2S N1S H1SB 109.5 . . ?
C2S N1S H1SC 109.5 . . ?
N1S C2S H2SA 109.2 . . ?
N1S C2S H2SB 109.2 . . ?
N1S C2S C3S 112.1(2) . . ?
H2SA C2S H2SB 107.9 . . ?
C3S C2S H2SA 109.2 . . ?
C3S C2S H2SB 109.2 . . ?
C2S C3S C2S 108.6(3) . 2_665 ?
C2S C3S H3SA 110.0 . . ?
C2S C3S H3SA 110.0 2_665 . ?
C2S C3S H3SB 110.0 . . ?
C2S C3S H3SB 110.0 2_665 . ?
H3SA C3S H3SB 108.4 . . ?

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 H1 O1 0.847(17) 2.14(2) 2.879(3) 145(3) . yes
N1S H1SA O1 0.89 1.85 2.742(3) 174.6 8_755 yes
N1S H1SB O2 0.89 1.85 2.726(4) 169.4 . yes
N1S H1SC O1A 0.89 2.02 2.90(2) 166.9 8_755 yes
N1S H1SC O1B 0.89 1.83 2.72(2) 177.9 8_755 yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cl1 C2 C3 C4 179.9(2) . . . . ?
N1 C1 C2 Cl1 -0.9(3) . . . . ?
N1 C1 C2 C3 179.3(3) . . . . ?
N1 C1 C6 Cl2 -3.0(3) . . . . ?
N1 C1 C6 C5 179.2(2) . . . . ?
N1 C7 C8 C9 179.2(2) . . . . ?
N1 C7 C12 C11 -179.8(2) . . . . ?
N1 C7 C12 C13 0.5(4) . . . . ?
C1 N1 C7 C8 -17.7(4) . . . . ?
C1 N1 C7 C12 163.3(2) . . . . ?
C1 C2 C3 C4 -0.3(4) . . . . ?
C2 C1 C6 Cl2 172.13(18) . . . . ?
C2 C1 C6 C5 -5.7(4) . . . . ?
C2 C3 C4 C5 -2.2(5) . . . . ?
C3 C4 C5 C6 0.6(4) . . . . ?
C4 C5 C6 Cl2 -174.3(2) . . . . ?
C4 C5 C6 C1 3.5(4) . . . . ?
C6 C1 C2 Cl1 -176.11(19) . . . . ?
C6 C1 C2 C3 4.1(4) . . . . ?
C7 N1 C1 C2 134.7(3) . . . . ?
C7 N1 C1 C6 -50.4(4) . . . . ?
C7 C8 C9 C10 0.8(4) . . . . ?
C7 C12 C13 C14 80.1(3) . . . . ?
C8 C7 C12 C11 1.1(4) . . . . ?
C8 C7 C12 C13 -178.6(2) . . . . ?
C8 C9 C10 C11 0.6(4) . . . . ?
C9 C10 C11 C12 -1.3(5) . . . . ?
C10 C11 C12 C7 0.4(4) . . . . ?
C10 C11 C12 C13 -179.9(3) . . . . ?
C11 C12 C13 C14 -99.6(3) . . . . ?
C12 C7 C8 C9 -1.7(4) . . . . ?
C12 C13 C14 O1 -57.1(4) . . . . ?
C12 C13 C14 O2 122.6(3) . . . . ?
N1S C2S C3S C2S -176.6(3) . . . 2_665 ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
####################################################################### 
# 
# 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_exp_392_cr_auto
_database_code_depnum_ccdc_archive 'CCDC 2246041'
loop_
_audit_author_name
_audit_author_address
'Christopher Richardson'
;University of Wollongong
Australia
;
_audit_update_record             
;
2024-05-13 deposited with the CCDC.	2024-05-23 downloaded from the CCDC.
;
_audit_creation_date             2024-05-13
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         
'2(C14 H10 Cl2 N O2), C3 H12 N2, 1.002(C2 H6 O), 2(H2 O)'
_chemical_formula_sum            'C33.01 H42.01 Cl4 N4 O7'
_chemical_formula_weight         748.57
_chemical_melting_point          ?
_chemical_oxdiff_formula         C33H40Cl4N4O6
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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.4529(4)
_cell_length_b                   10.1381(2)
_cell_length_c                   19.0267(6)
_cell_angle_alpha                84.791(2)
_cell_angle_beta                 89.345(3)
_cell_angle_gamma                88.234(2)
_cell_volume                     1814.95(10)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    14768
_cell_measurement_temperature    294(1)
_cell_measurement_theta_max      28.3620
_cell_measurement_theta_min      2.0090
_shelx_estimated_absorpt_T_max   0.956
_shelx_estimated_absorpt_T_min   0.861
_exptl_absorpt_coefficient_mu    0.377
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.91594
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.123a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.370
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             784
_exptl_crystal_recrystallization_method 'from ethanol-water reaction solution'
_exptl_crystal_size_max          0.41
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.12
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0348
_diffrn_reflns_av_unetI/netI     0.0368
_diffrn_reflns_Laue_measured_fraction_full 0.990
_diffrn_reflns_Laue_measured_fraction_max 0.975
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_number            59277
_diffrn_reflns_point_group_measured_fraction_full 0.990
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.573
_diffrn_reflns_theta_min         2.018
_diffrn_ambient_temperature      294(1)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.975
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -74.00 110.00   0.50   10.00    --   20.00  54.00 153.45  368
  2  ω    -74.00 110.00   0.50   10.00    --   20.00  54.00   8.90  368
  3  ω    -74.00 110.00   0.50   10.00    --   20.00  54.00-146.13  368
  4  ω    -74.00 110.00   0.50   10.00    --   20.00  54.00-146.13  368
  5  ω    -74.00 110.00   0.50   10.00    --   20.00  54.00 -93.84  368
  6  ω    -74.00 110.00   0.50   10.00    --   20.00  54.00 -93.84  368
  7  ω    -74.00 110.00   0.50   10.00    --   20.00  54.00 -48.20  368
  8  ω    -74.00 110.00   0.50   10.00    --   20.00  54.00 120.00  368
  9  ω    -74.00 110.00   0.50   10.00    --   20.00  54.00 -69.88  368
 10  ω    -74.00 110.00   0.50   10.00    --   20.00  54.00-180.00  368
 11  ω    -74.00 110.00   0.50   10.00    --   20.00  54.00 -30.00  368
 12  ω    -67.00 -32.00   0.50   10.00    --   20.00  54.00  60.00   70
 13  ω    -74.00 -48.00   0.50   10.00    --   20.00  54.00 150.00   52
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini II'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0282223000
_diffrn_orient_matrix_UB_12      0.0410728000
_diffrn_orient_matrix_UB_13      0.0243080000
_diffrn_orient_matrix_UB_21      -0.0258025000
_diffrn_orient_matrix_UB_22      -0.0429427000
_diffrn_orient_matrix_UB_23      0.0284671000
_diffrn_orient_matrix_UB_31      0.0646045000
_diffrn_orient_matrix_UB_32      -0.0375360000
_diffrn_orient_matrix_UB_33      0.0003731000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                6297
_reflns_number_total             9918
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.713
_refine_diff_density_min         -0.867
_refine_diff_density_rms         0.069
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     536
_refine_ls_number_reflns         9918
_refine_ls_number_restraints     77
_refine_ls_R_factor_all          0.1000
_refine_ls_R_factor_gt           0.0615
_refine_ls_restrained_S_all      1.058
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1119P)²+0.7661P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1762
_refine_ls_wR_factor_ref         0.2059
_refine_special_details          
'Ended up constraining the ADPs of two of the three disordered ethanol components to be the same. All ethanol molecules are rigid groups.'
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups, All N(H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups, All O(H,H) groups
2. Restrained distances
 N1B-H1B = N1A-H1A
 0.86 with sigma of 0.02
 C3PB-C2PB = C4PB-C3PB = C2PA-C3PA = C3PA-C4PA
 1.5 with sigma of 0.01
 N1PA-C2PA = N1PB-C2PB = N5PA-C4PA = N5PB-C4PB
 1.48 with sigma of 0.01
3. Rigid bond restraints
 O1T, C1T, C2T
 with sigma for 1-2 distances of 0.01 and sigma for 1-3 distances of 0.01
4. Uiso/Uaniso restraints and constraints
O1E \\sim C1E \\sim C2E: within 2A with sigma of 0.02 and sigma for terminal
atoms of 0.04 within 2A
O1O \\sim C1O \\sim C2O: within 2A with sigma of 0.01 and sigma for terminal
atoms of 0.02 within 2A
O1T \\sim C1T \\sim C2T: within 2A with sigma of 0.02 and sigma for terminal
atoms of 0.04 within 2A
Uanis(C2T) = Uanis(C2E)
Uanis(C1T) = Uanis(C1E)
5. Rigid body (RIGU) restrains
 O1O, C1O, C2O
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 O1E, C1E, C2E
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
 O1T, C1T, C2T
 with sigma for 1-2 distances of 0.004 and sigma for 1-3 distances of 0.004
6. Others
 1*[Sof(O1T)+Sof(H1T)+Sof(C1T)+Sof(H1TA)+Sof(H1TB)+Sof(C2T)+Sof(H2TA)+
 Sof(H2TB)+Sof(H2TC)]+1*[Sof(O1O)+Sof(H1O)+Sof(C1O)+Sof(H1OA)+Sof(H1OB)+
 Sof(C2O)+Sof(H2OA)+Sof(H2OB)+Sof(H2OC)]+1*[Sof(O1E)+Sof(H1E)+Sof(C1E)+
 Sof(H1EA)+Sof(H1EB)+Sof(C2E)+Sof(H2EA)+Sof(H2EB)+Sof(H2EC)]=1 with esd of 0.001
 Sof(N1PB)=Sof(H1PA)=Sof(H1PB)=Sof(H1PC)=Sof(C2PB)=Sof(H2PA)=Sof(H2PB)=
 Sof(C3PB)=Sof(H3PA)=Sof(H3PB)=Sof(C4PB)=Sof(H4PA)=Sof(H4PB)=Sof(N5PB)=
 Sof(H5PA)=Sof(H5PB)=Sof(H5PC)=1-FVAR(1)
 Sof(C2PA)=Sof(H2PC)=Sof(H2PD)=Sof(C3PA)=Sof(H3PC)=Sof(H3PD)=Sof(C4PA)=
 Sof(H4PC)=Sof(H4PD)=Sof(N5PA)=Sof(H5PD)=Sof(H5PE)=Sof(H5PF)=Sof(N1PA)=
 Sof(H1PD)=Sof(H1PE)=Sof(H1PF)=FVAR(1)
 Sof(O1T)=Sof(H1T)=Sof(C1T)=Sof(H1TA)=Sof(H1TB)=Sof(C2T)=Sof(H2TA)=Sof(H2TB)=
 Sof(H2TC)=FVAR(2)
 Sof(O1O)=Sof(H1O)=Sof(C1O)=Sof(H1OA)=Sof(H1OB)=Sof(C2O)=Sof(H2OA)=Sof(H2OB)=
 Sof(H2OC)=FVAR(3)
 Sof(O1E)=Sof(H1E)=Sof(C1E)=Sof(H1EA)=Sof(H1EB)=Sof(C2E)=Sof(H2EA)=Sof(H2EB)=
 Sof(H2EC)=FVAR(4)
7.a Free rotating group:
 O1E(C1E,C2E), O1O(C1O,C2O), O1T(C1T,C2T), O1W(H1WA,H1WB), O2W(H2WA,H2WB)
7.b Secondary CH2 refined with riding coordinates:
 C13A(H13A,H13B), C13B(H13C,H13D), C1E(H1EA,H1EB), C1O(H1OA,H1OB), C2PB(H2PA,
 H2PB), C3PB(H3PA,H3PB), C4PB(H4PA,H4PB), C2PA(H2PC,H2PD), C3PA(H3PC,H3PD),
 C4PA(H4PC,H4PD), C1T(H1TA,H1TB)
7.c Me refined with riding coordinates:
 C2E(H2EA,H2EB,H2EC), C2O(H2OA,H2OB,H2OC), C2T(H2TA,H2TB,H2TC)
7.d Aromatic/amide H refined with riding coordinates:
 C3A(H3A), C4A(H4A), C5A(H5A), C8A(H8A), C9A(H9A), C10A(H10A), C11A(H11A),
 C3B(H3B), C4B(H4B), C5B(H5B), C8B(H8B), C9B(H9B), C10B(H10B), C11B(H11B)
7.e Idealised Me refined as rotating group:
 N1PB(H1PA,H1PB,H1PC), N5PB(H5PA,H5PB,H5PC), N5PA(H5PD,H5PE,H5PF), N1PA(H1PD,
 H1PE,H1PF)
7.f Idealised tetrahedral OH refined as rotating group:
 O1E(H1E), O1O(H1O), O1T(H1T)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1A Cl 0.29711(8) 1.03928(8) 0.75028(4) 0.0569(2) Uani 1 1 d . . . . .
O1A O 0.5298(3) 0.8282(2) 0.65394(11) 0.0595(6) Uani 1 1 d . . . . .
N1A N 0.5067(2) 0.8271(2) 0.80654(12) 0.0436(5) Uani 1 1 d D . . . .
H1A H 0.477(3) 0.844(3) 0.7633(11) 0.060(10) Uiso 1 1 d D . . . .
C1A C 0.4274(3) 0.8874(2) 0.85760(13) 0.0360(5) Uani 1 1 d . . . . .
Cl2A Cl 0.55078(8) 0.71614(7) 0.96010(4) 0.05045(19) Uani 1 1 d . . . . .
O2A O 0.5810(5) 0.6529(3) 0.59842(15) 0.1189(14) Uani 1 1 d . . . . .
C2A C 0.3236(3) 0.9862(2) 0.83941(13) 0.0393(5) Uani 1 1 d . . . . .
C3A C 0.2396(3) 1.0447(3) 0.88888(15) 0.0455(6) Uani 1 1 d . . . . .
H3A H 0.171015 1.108773 0.874299 0.055 Uiso 1 1 calc R U . . .
C4A C 0.2582(3) 1.0072(3) 0.96008(16) 0.0502(7) Uani 1 1 d . . . . .
H4A H 0.204715 1.048258 0.993667 0.060 Uiso 1 1 calc R U . . .
C5A C 0.3575(3) 0.9079(3) 0.98089(14) 0.0450(6) Uani 1 1 d . . . . .
H5A H 0.370262 0.881620 1.028561 0.054 Uiso 1 1 calc R U . . .
C6A C 0.4377(3) 0.8479(2) 0.93038(13) 0.0383(5) Uani 1 1 d . . . . .
C7A C 0.6562(3) 0.8125(2) 0.80739(12) 0.0374(5) Uani 1 1 d . . . . .
C8A C 0.7402(3) 0.8856(3) 0.84862(14) 0.0438(6) Uani 1 1 d . . . . .
H8A H 0.697690 0.947778 0.875806 0.053 Uiso 1 1 calc R U . . .
C9A C 0.8858(3) 0.8669(3) 0.84958(16) 0.0517(7) Uani 1 1 d . . . . .
H9A H 0.940352 0.915283 0.877822 0.062 Uiso 1 1 calc R U . . .
C10A C 0.9505(3) 0.7759(3) 0.80843(18) 0.0587(8) Uani 1 1 d . . . . .
H10A H 1.048296 0.762764 0.809016 0.070 Uiso 1 1 calc R U . . .
C11A C 0.8685(3) 0.7049(3) 0.76661(16) 0.0517(7) Uani 1 1 d . . . . .
H11A H 0.912749 0.644898 0.738702 0.062 Uiso 1 1 calc R U . . .
C12A C 0.7206(3) 0.7202(3) 0.76481(13) 0.0416(6) Uani 1 1 d . . . . .
C13A C 0.6340(3) 0.6373(3) 0.72010(14) 0.0455(6) Uani 1 1 d . . . . .
H13A H 0.555496 0.601963 0.748394 0.055 Uiso 1 1 calc R U . . .
H13B H 0.692535 0.562798 0.707276 0.055 Uiso 1 1 calc R U . . .
C14A C 0.5753(4) 0.7112(3) 0.65287(15) 0.0515(7) Uani 1 1 d . . . . .
Cl1B Cl 0.95257(7) 0.22975(7) 0.96176(4) 0.04842(18) Uani 1 1 d . . . . .
O1B O 0.9694(3) 0.3230(2) 0.65336(12) 0.0711(7) Uani 1 1 d . . . . .
N1B N 0.9951(2) 0.3269(2) 0.80512(12) 0.0432(5) Uani 1 1 d D . . . .
H1B H 1.029(3) 0.330(3) 0.7612(11) 0.059(9) Uiso 1 1 d D . . . .
C1B C 1.0741(3) 0.3870(2) 0.85405(13) 0.0365(5) Uani 1 1 d . . . . .
Cl2B Cl 1.21116(8) 0.51403(9) 0.74270(4) 0.0589(2) Uani 1 1 d . . . . .
O2B O 0.9079(3) 0.1537(2) 0.59683(11) 0.0625(6) Uani 1 1 d . . . . .
C2B C 1.0632(3) 0.3545(2) 0.92754(14) 0.0388(5) Uani 1 1 d . . . . .
C3B C 1.1422(3) 0.4170(3) 0.97554(15) 0.0454(6) Uani 1 1 d . . . . .
H3B H 1.129734 0.395779 1.023752 0.055 Uiso 1 1 calc R U . . .
C4B C 1.2390(3) 0.5107(3) 0.95151(16) 0.0494(7) Uani 1 1 d . . . . .
H4B H 1.290216 0.553978 0.983493 0.059 Uiso 1 1 calc R U . . .
C5B C 1.2593(3) 0.5396(3) 0.88025(16) 0.0474(6) Uani 1 1 d . . . . .
H5B H 1.326761 0.600144 0.863888 0.057 Uiso 1 1 calc R U . . .
C6B C 1.1790(3) 0.4782(2) 0.83257(14) 0.0399(5) Uani 1 1 d . . . . .
C7B C 0.8442(3) 0.3158(2) 0.80865(13) 0.0372(5) Uani 1 1 d . . . . .
C8B C 0.7605(3) 0.3931(3) 0.85071(14) 0.0421(6) Uani 1 1 d . . . . .
H8B H 0.802026 0.455556 0.876180 0.051 Uiso 1 1 calc R U . . .
C9B C 0.6148(3) 0.3772(3) 0.85466(15) 0.0492(7) Uani 1 1 d . . . . .
H9B H 0.559698 0.428697 0.883090 0.059 Uiso 1 1 calc R U . . .
C10B C 0.5516(3) 0.2861(3) 0.81704(17) 0.0561(7) Uani 1 1 d . . . . .
H10B H 0.454507 0.274216 0.820540 0.067 Uiso 1 1 calc R U . . .
C11B C 0.6359(3) 0.2116(3) 0.77327(16) 0.0510(7) Uani 1 1 d . . . . .
H11B H 0.592998 0.151646 0.746706 0.061 Uiso 1 1 calc R U . . .
C12B C 0.7823(3) 0.2244(2) 0.76831(13) 0.0395(5) Uani 1 1 d . . . . .
C13B C 0.8697(3) 0.1393(3) 0.72181(14) 0.0458(6) Uani 1 1 d . . . . .
H13C H 0.814285 0.064565 0.711439 0.055 Uiso 1 1 calc R U . . .
H13D H 0.952393 0.104445 0.747814 0.055 Uiso 1 1 calc R U . . .
C14B C 0.9185(3) 0.2116(3) 0.65234(14) 0.0459(6) Uani 1 1 d . . . . .
O1E O 0.2491(6) 0.2401(5) 0.5993(3) 0.0344(15) Uani 0.292(4) 1 d G U P A 1
H1E H 0.212710 0.310306 0.609722 0.052 Uiso 0.292(4) 1 calc R U P A 1
C1E C 0.3625(16) 0.2666(16) 0.5506(8) 0.138(4) Uani 0.292(4) 1 d G U P A 1
H1EA H 0.327862 0.273071 0.502573 0.166 Uiso 0.292(4) 1 calc R U P A 1
H1EB H 0.434071 0.195908 0.555877 0.166 Uiso 0.292(4) 1 calc R U P A 1
C2E C 0.4243(19) 0.3962(17) 0.5664(11) 0.138(4) Uani 0.292(4) 1 d G U P A 1
H2EA H 0.501220 0.417015 0.534341 0.207 Uiso 0.292(4) 1 calc R U P A 1
H2EB H 0.352554 0.465417 0.560911 0.207 Uiso 0.292(4) 1 calc R U P A 1
H2EC H 0.458295 0.388593 0.613980 0.207 Uiso 0.292(4) 1 calc R U P A 1
O1O O 0.4956(10) 0.3753(8) 0.6327(4) 0.057(3) Uani 0.255(6) 1 d G U P B 3
H1O H 0.577898 0.393462 0.639653 0.085 Uiso 0.255(6) 1 calc R U P B 3
C1O C 0.493(3) 0.2546(12) 0.5997(10) 0.124(6) Uani 0.255(6) 1 d G U P B 3
H1OA H 0.395766 0.229950 0.593209 0.149 Uiso 0.255(6) 1 calc R U P B 3
H1OB H 0.540649 0.183842 0.628882 0.149 Uiso 0.255(6) 1 calc R U P B 3
C2O C 0.567(2) 0.277(2) 0.5292(6) 0.126(7) Uani 0.255(6) 1 d G U P B 3
H2OA H 0.567005 0.197500 0.505640 0.189 Uiso 0.255(6) 1 calc R U P B 3
H2OB H 0.518722 0.347350 0.500829 0.189 Uiso 0.255(6) 1 calc R U P B 3
H2OC H 0.662975 0.301442 0.536347 0.189 Uiso 0.255(6) 1 calc R U P B 3
N1PB N -0.019(2) 0.728(2) 0.5329(11) 0.087(7) Uani 0.427(8) 1 d D . P C 1
H1PA H 0.013261 0.756968 0.490346 0.105 Uiso 0.427(8) 1 calc R U P C 1
H1PB H -0.082161 0.785773 0.547780 0.105 Uiso 0.427(8) 1 calc R U P C 1
H1PC H -0.059111 0.649983 0.530532 0.105 Uiso 0.427(8) 1 calc R U P C 1
C2PB C 0.101(2) 0.7110(13) 0.5829(10) 0.065(4) Uani 0.427(8) 1 d D . P C 1
H2PA H 0.185582 0.690389 0.556435 0.078 Uiso 0.427(8) 1 calc R U P C 1
H2PB H 0.082858 0.634684 0.615993 0.078 Uiso 0.427(8) 1 calc R U P C 1
C3PB C 0.1313(9) 0.8259(8) 0.6249(4) 0.060(2) Uani 0.427(8) 1 d D . P C 1
H3PA H 0.046672 0.847822 0.651222 0.072 Uiso 0.427(8) 1 calc R U P C 1
H3PB H 0.204576 0.798037 0.658764 0.072 Uiso 0.427(8) 1 calc R U P C 1
C4PB C 0.1774(12) 0.9479(10) 0.5820(7) 0.050(2) Uani 0.427(8) 1 d D . P C 1
H4PA H 0.139180 0.946772 0.534993 0.060 Uiso 0.427(8) 1 calc R U P C 1
H4PB H 0.134075 1.023735 0.602447 0.060 Uiso 0.427(8) 1 calc R U P C 1
N5PB N 0.3274(14) 0.9697(19) 0.5749(8) 0.051(2) Uani 0.427(8) 1 d D . P C 1
H5PA H 0.349966 0.984857 0.529380 0.061 Uiso 0.427(8) 1 calc R U P C 1
H5PB H 0.375436 0.898233 0.593398 0.061 Uiso 0.427(8) 1 calc R U P C 1
H5PC H 0.349211 1.039362 0.597450 0.061 Uiso 0.427(8) 1 calc R U P C 1
C2PA C 0.0740(14) 0.6764(12) 0.5791(8) 0.064(3) Uani 0.573(8) 1 d D . P C 2
H2PC H 0.097014 0.584179 0.573168 0.077 Uiso 0.573(8) 1 calc R U P C 2
H2PD H 0.036132 0.681919 0.626362 0.077 Uiso 0.573(8) 1 calc R U P C 2
C3PA C 0.2060(7) 0.7570(6) 0.5693(3) 0.0601(17) Uani 0.573(8) 1 d D . P C 2
H3PC H 0.280942 0.712675 0.597698 0.072 Uiso 0.573(8) 1 calc R U P C 2
H3PD H 0.235876 0.759370 0.520262 0.072 Uiso 0.573(8) 1 calc R U P C 2
C4PA C 0.1878(12) 0.8959(7) 0.5888(6) 0.061(2) Uani 0.573(8) 1 d D . P C 2
H4PC H 0.106384 0.942220 0.566554 0.073 Uiso 0.573(8) 1 calc R U P C 2
H4PD H 0.183596 0.901059 0.639479 0.073 Uiso 0.573(8) 1 calc R U P C 2
N5PA N 0.3221(14) 0.9405(16) 0.5575(7) 0.087(4) Uani 0.573(8) 1 d D . P C 2
H5PD H 0.336148 0.905385 0.516707 0.104 Uiso 0.573(8) 1 calc R U P C 2
H5PE H 0.392429 0.914686 0.586792 0.104 Uiso 0.573(8) 1 calc R U P C 2
H5PF H 0.319366 1.028446 0.550012 0.104 Uiso 0.573(8) 1 calc R U P C 2
N1PA N -0.0322(13) 0.7281(14) 0.5267(7) 0.046(2) Uani 0.573(8) 1 d D . P C 2
H1PD H 0.011044 0.753897 0.486163 0.055 Uiso 0.573(8) 1 calc R U P C 2
H1PE H -0.079591 0.796727 0.542503 0.055 Uiso 0.573(8) 1 calc R U P C 2
H1PF H -0.092223 0.664684 0.519641 0.055 Uiso 0.573(8) 1 calc R U P C 2
O1T O 0.4701(7) 0.1783(5) 0.5215(2) 0.073(2) Uani 0.455(6) 1 d G U P D 2
H1T H 0.496829 0.216475 0.484085 0.109 Uiso 0.455(6) 1 calc R U P D 2
C1T C 0.5081(11) 0.2521(15) 0.5783(6) 0.138(4) Uani 0.455(6) 1 d G U P D 2
H1TA H 0.576103 0.318301 0.562340 0.166 Uiso 0.455(6) 1 calc R U P D 2
H1TB H 0.550398 0.193685 0.616073 0.166 Uiso 0.455(6) 1 calc R U P D 2
C2T C 0.3745(16) 0.3181(12) 0.6043(6) 0.138(4) Uani 0.455(6) 1 d G U P D 2
H2TA H 0.396688 0.368807 0.642749 0.207 Uiso 0.455(6) 1 calc R U P D 2
H2TB H 0.333791 0.375784 0.566575 0.207 Uiso 0.455(6) 1 calc R U P D 2
H2TC H 0.308197 0.251710 0.620075 0.207 Uiso 0.455(6) 1 calc R U P D 2
O1W O 0.8215(4) 0.4956(3) 0.55248(16) 0.0863(8) Uani 1 1 d G . . . .
H1WA H 0.860928 0.436391 0.580858 0.130 Uiso 1 1 d G U . . .
H1WB H 0.746826 0.518814 0.574008 0.130 Uiso 1 1 d G U . . .
O2W O 0.7822(3) 0.9307(3) 0.57476(14) 0.0799(8) Uani 1 1 d G . . . .
H2WA H 0.718067 0.905942 0.604323 0.120 Uiso 1 1 d G U . . .
H2WB H 0.841168 0.969168 0.598747 0.120 Uiso 1 1 d G 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
Cl1A C2A 1.750(3) . ?
O1A C14A 1.250(3) . ?
N1A H1A 0.872(18) . ?
N1A C1A 1.394(3) . ?
N1A C7A 1.416(3) . ?
C1A C2A 1.404(3) . ?
C1A C6A 1.410(3) . ?
Cl2A C6A 1.742(3) . ?
O2A C14A 1.238(4) . ?
C2A C3A 1.386(4) . ?
C3A H3A 0.9300 . ?
C3A C4A 1.385(4) . ?
C4A H4A 0.9300 . ?
C4A C5A 1.389(4) . ?
C5A H5A 0.9300 . ?
C5A C6A 1.389(4) . ?
C7A C8A 1.397(4) . ?
C7A C12A 1.412(3) . ?
C8A H8A 0.9300 . ?
C8A C9A 1.384(4) . ?
C9A H9A 0.9300 . ?
C9A C10A 1.387(5) . ?
C10A H10A 0.9300 . ?
C10A C11A 1.380(5) . ?
C11A H11A 0.9300 . ?
C11A C12A 1.402(4) . ?
C12A C13A 1.513(4) . ?
C13A H13A 0.9700 . ?
C13A H13B 0.9700 . ?
C13A C14A 1.524(4) . ?
Cl1B C2B 1.741(3) . ?
O1B C14B 1.244(3) . ?
N1B H1B 0.892(18) . ?
N1B C1B 1.393(3) . ?
N1B C7B 1.435(3) . ?
C1B C2B 1.411(4) . ?
C1B C6B 1.409(4) . ?
Cl2B C6B 1.741(3) . ?
O2B C14B 1.260(3) . ?
C2B C3B 1.394(4) . ?
C3B H3B 0.9300 . ?
C3B C4B 1.384(4) . ?
C4B H4B 0.9300 . ?
C4B C5B 1.373(4) . ?
C5B H5B 0.9300 . ?
C5B C6B 1.391(4) . ?
C7B C8B 1.394(3) . ?
C7B C12B 1.401(4) . ?
C8B H8B 0.9300 . ?
C8B C9B 1.392(4) . ?
C9B H9B 0.9300 . ?
C9B C10B 1.373(5) . ?
C10B H10B 0.9300 . ?
C10B C11B 1.401(4) . ?
C11B H11B 0.9300 . ?
C11B C12B 1.395(4) . ?
C12B C13B 1.513(4) . ?
C13B H13C 0.9700 . ?
C13B H13D 0.9700 . ?
C13B C14B 1.526(4) . ?
O1E H1E 0.8200 . ?
O1E C1E 1.4248 . ?
C1E H1EA 0.9700 . ?
C1E H1EB 0.9700 . ?
C1E C2E 1.5100 . ?
C2E H2EA 0.9600 . ?
C2E H2EB 0.9600 . ?
C2E H2EC 0.9600 . ?
O1O H1O 0.8200 . ?
O1O C1O 1.4255 . ?
C1O H1OA 0.9700 . ?
C1O H1OB 0.9700 . ?
C1O C2O 1.5100 . ?
C2O H2OA 0.9600 . ?
C2O H2OB 0.9600 . ?
C2O H2OC 0.9600 . ?
N1PB H1PA 0.8900 . ?
N1PB H1PB 0.8900 . ?
N1PB H1PC 0.8900 . ?
N1PB C2PB 1.481(9) . ?
C2PB H2PA 0.9700 . ?
C2PB H2PB 0.9700 . ?
C2PB C3PB 1.507(9) . ?
C3PB H3PA 0.9700 . ?
C3PB H3PB 0.9700 . ?
C3PB C4PB 1.492(8) . ?
C4PB H4PA 0.9700 . ?
C4PB H4PB 0.9700 . ?
C4PB N5PB 1.444(9) . ?
N5PB H5PA 0.8900 . ?
N5PB H5PB 0.8900 . ?
N5PB H5PC 0.8900 . ?
C2PA H2PC 0.9700 . ?
C2PA H2PD 0.9700 . ?
C2PA C3PA 1.512(8) . ?
C2PA N1PA 1.474(8) . ?
C3PA H3PC 0.9700 . ?
C3PA H3PD 0.9700 . ?
C3PA C4PA 1.493(7) . ?
C4PA H4PC 0.9700 . ?
C4PA H4PD 0.9700 . ?
C4PA N5PA 1.463(8) . ?
N5PA H5PD 0.8900 . ?
N5PA H5PE 0.8900 . ?
N5PA H5PF 0.8900 . ?
N1PA H1PD 0.8900 . ?
N1PA H1PE 0.8900 . ?
N1PA H1PF 0.8900 . ?
O1T H1T 0.8200 . ?
O1T C1T 1.4252 . ?
C1T H1TA 0.9700 . ?
C1T H1TB 0.9700 . ?
C1T C2T 1.5098 . ?
C2T H2TA 0.9600 . ?
C2T H2TB 0.9600 . ?
C2T H2TC 0.9600 . ?
O1W H1WA 0.8501 . ?
O1W H1WB 0.8497 . ?
O2W H2WA 0.8500 . ?
O2W H2WB 0.8502 . ?

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
C1A N1A H1A 115(2) . . ?
C1A N1A C7A 123.9(2) . . ?
C7A N1A H1A 110(2) . . ?
N1A C1A C2A 121.8(2) . . ?
N1A C1A C6A 123.0(2) . . ?
C2A C1A C6A 115.0(2) . . ?
C1A C2A Cl1A 119.12(19) . . ?
C3A C2A Cl1A 117.7(2) . . ?
C3A C2A C1A 123.1(2) . . ?
C2A C3A H3A 120.1 . . ?
C4A C3A C2A 119.8(2) . . ?
C4A C3A H3A 120.1 . . ?
C3A C4A H4A 120.3 . . ?
C3A C4A C5A 119.4(3) . . ?
C5A C4A H4A 120.3 . . ?
C4A C5A H5A 120.1 . . ?
C6A C5A C4A 119.9(3) . . ?
C6A C5A H5A 120.1 . . ?
C1A C6A Cl2A 120.14(19) . . ?
C5A C6A C1A 122.6(2) . . ?
C5A C6A Cl2A 117.2(2) . . ?
C8A C7A N1A 122.3(2) . . ?
C8A C7A C12A 119.7(2) . . ?
C12A C7A N1A 118.0(2) . . ?
C7A C8A H8A 119.5 . . ?
C9A C8A C7A 120.9(3) . . ?
C9A C8A H8A 119.5 . . ?
C8A C9A H9A 120.0 . . ?
C8A C9A C10A 120.0(3) . . ?
C10A C9A H9A 120.0 . . ?
C9A C10A H10A 120.3 . . ?
C11A C10A C9A 119.4(3) . . ?
C11A C10A H10A 120.3 . . ?
C10A C11A H11A 118.9 . . ?
C10A C11A C12A 122.2(3) . . ?
C12A C11A H11A 118.9 . . ?
C7A C12A C13A 121.7(2) . . ?
C11A C12A C7A 117.7(3) . . ?
C11A C12A C13A 120.6(2) . . ?
C12A C13A H13A 108.6 . . ?
C12A C13A H13B 108.6 . . ?
C12A C13A C14A 114.7(2) . . ?
H13A C13A H13B 107.6 . . ?
C14A C13A H13A 108.6 . . ?
C14A C13A H13B 108.6 . . ?
O1A C14A C13A 119.6(2) . . ?
O2A C14A O1A 123.0(3) . . ?
O2A C14A C13A 117.4(3) . . ?
C1B N1B H1B 117(2) . . ?
C1B N1B C7B 124.1(2) . . ?
C7B N1B H1B 113(2) . . ?
N1B C1B C2B 123.1(2) . . ?
N1B C1B C6B 121.5(2) . . ?
C6B C1B C2B 115.2(2) . . ?
C1B C2B Cl1B 120.67(19) . . ?
C3B C2B Cl1B 117.2(2) . . ?
C3B C2B C1B 122.1(2) . . ?
C2B C3B H3B 120.0 . . ?
C4B C3B C2B 120.1(3) . . ?
C4B C3B H3B 120.0 . . ?
C3B C4B H4B 120.1 . . ?
C5B C4B C3B 119.8(3) . . ?
C5B C4B H4B 120.1 . . ?
C4B C5B H5B 120.0 . . ?
C4B C5B C6B 120.0(3) . . ?
C6B C5B H5B 120.0 . . ?
C1B C6B Cl2B 118.7(2) . . ?
C5B C6B C1B 122.7(2) . . ?
C5B C6B Cl2B 118.6(2) . . ?
C8B C7B N1B 121.5(2) . . ?
C8B C7B C12B 120.4(2) . . ?
C12B C7B N1B 118.1(2) . . ?
C7B C8B H8B 119.9 . . ?
C9B C8B C7B 120.1(3) . . ?
C9B C8B H8B 119.9 . . ?
C8B C9B H9B 119.6 . . ?
C10B C9B C8B 120.7(3) . . ?
C10B C9B H9B 119.6 . . ?
C9B C10B H10B 120.6 . . ?
C9B C10B C11B 118.8(3) . . ?
C11B C10B H10B 120.6 . . ?
C10B C11B H11B 119.0 . . ?
C12B C11B C10B 122.1(3) . . ?
C12B C11B H11B 119.0 . . ?
C7B C12B C13B 121.9(2) . . ?
C11B C12B C7B 117.8(2) . . ?
C11B C12B C13B 120.3(2) . . ?
C12B C13B H13C 108.7 . . ?
C12B C13B H13D 108.7 . . ?
C12B C13B C14B 114.4(2) . . ?
H13C C13B H13D 107.6 . . ?
C14B C13B H13C 108.7 . . ?
C14B C13B H13D 108.7 . . ?
O1B C14B O2B 123.2(3) . . ?
O1B C14B C13B 118.6(2) . . ?
O2B C14B C13B 118.1(2) . . ?
C1E O1E H1E 109.5 . . ?
O1E C1E H1EA 110.2 . . ?
O1E C1E H1EB 110.2 . . ?
O1E C1E C2E 107.4 . . ?
H1EA C1E H1EB 108.5 . . ?
C2E C1E H1EA 110.2 . . ?
C2E C1E H1EB 110.2 . . ?
C1E C2E H2EA 109.5 . . ?
C1E C2E H2EB 109.5 . . ?
C1E C2E H2EC 109.5 . . ?
H2EA C2E H2EB 109.5 . . ?
H2EA C2E H2EC 109.5 . . ?
H2EB C2E H2EC 109.5 . . ?
C1O O1O H1O 109.5 . . ?
O1O C1O H1OA 110.2 . . ?
O1O C1O H1OB 110.2 . . ?
O1O C1O C2O 107.4 . . ?
H1OA C1O H1OB 108.5 . . ?
C2O C1O H1OA 110.2 . . ?
C2O C1O H1OB 110.2 . . ?
C1O C2O H2OA 109.5 . . ?
C1O C2O H2OB 109.5 . . ?
C1O C2O H2OC 109.5 . . ?
H2OA C2O H2OB 109.5 . . ?
H2OA C2O H2OC 109.5 . . ?
H2OB C2O H2OC 109.5 . . ?
H1PA N1PB H1PB 109.5 . . ?
H1PA N1PB H1PC 109.5 . . ?
H1PB N1PB H1PC 109.5 . . ?
C2PB N1PB H1PA 109.5 . . ?
C2PB N1PB H1PB 109.5 . . ?
C2PB N1PB H1PC 109.5 . . ?
N1PB C2PB H2PA 107.9 . . ?
N1PB C2PB H2PB 107.9 . . ?
N1PB C2PB C3PB 117.5(15) . . ?
H2PA C2PB H2PB 107.2 . . ?
C3PB C2PB H2PA 107.9 . . ?
C3PB C2PB H2PB 107.9 . . ?
C2PB C3PB H3PA 108.5 . . ?
C2PB C3PB H3PB 108.5 . . ?
H3PA C3PB H3PB 107.5 . . ?
C4PB C3PB C2PB 114.9(10) . . ?
C4PB C3PB H3PA 108.5 . . ?
C4PB C3PB H3PB 108.5 . . ?
C3PB C4PB H4PA 107.8 . . ?
C3PB C4PB H4PB 107.8 . . ?
H4PA C4PB H4PB 107.1 . . ?
N5PB C4PB C3PB 118.0(11) . . ?
N5PB C4PB H4PA 107.8 . . ?
N5PB C4PB H4PB 107.8 . . ?
C4PB N5PB H5PA 109.5 . . ?
C4PB N5PB H5PB 109.5 . . ?
C4PB N5PB H5PC 109.5 . . ?
H5PA N5PB H5PB 109.5 . . ?
H5PA N5PB H5PC 109.5 . . ?
H5PB N5PB H5PC 109.5 . . ?
H2PC C2PA H2PD 108.2 . . ?
C3PA C2PA H2PC 109.8 . . ?
C3PA C2PA H2PD 109.8 . . ?
N1PA C2PA H2PC 109.8 . . ?
N1PA C2PA H2PD 109.8 . . ?
N1PA C2PA C3PA 109.4(11) . . ?
C2PA C3PA H3PC 108.7 . . ?
C2PA C3PA H3PD 108.7 . . ?
H3PC C3PA H3PD 107.6 . . ?
C4PA C3PA C2PA 114.2(8) . . ?
C4PA C3PA H3PC 108.7 . . ?
C4PA C3PA H3PD 108.7 . . ?
C3PA C4PA H4PC 112.7 . . ?
C3PA C4PA H4PD 112.7 . . ?
H4PC C4PA H4PD 110.2 . . ?
N5PA C4PA C3PA 95.1(9) . . ?
N5PA C4PA H4PC 112.7 . . ?
N5PA C4PA H4PD 112.7 . . ?
C4PA N5PA H5PD 109.5 . . ?
C4PA N5PA H5PE 109.5 . . ?
C4PA N5PA H5PF 109.5 . . ?
H5PD N5PA H5PE 109.5 . . ?
H5PD N5PA H5PF 109.5 . . ?
H5PE N5PA H5PF 109.5 . . ?
C2PA N1PA H1PD 109.5 . . ?
C2PA N1PA H1PE 109.5 . . ?
C2PA N1PA H1PF 109.5 . . ?
H1PD N1PA H1PE 109.5 . . ?
H1PD N1PA H1PF 109.5 . . ?
H1PE N1PA H1PF 109.5 . . ?
C1T O1T H1T 109.5 . . ?
O1T C1T H1TA 110.2 . . ?
O1T C1T H1TB 110.2 . . ?
O1T C1T C2T 107.4 . . ?
H1TA C1T H1TB 108.5 . . ?
C2T C1T H1TA 110.2 . . ?
C2T C1T H1TB 110.2 . . ?
C1T C2T H2TA 109.5 . . ?
C1T C2T H2TB 109.5 . . ?
C1T C2T H2TC 109.5 . . ?
H2TA C2T H2TB 109.5 . . ?
H2TA C2T H2TC 109.5 . . ?
H2TB C2T H2TC 109.5 . . ?
H1WA O1W H1WB 104.5 . . ?
H2WA O2W H2WB 104.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
C2O H2OB O2A 0.96 2.12 2.840(14) 130.5 2_666 yes
N1PB H1PA O2B 0.89 1.97 2.85(2) 171.2 2_666 yes
N5PB H5PB O1A 0.89 1.95 2.736(19) 147.1 . yes
N5PB H5PC O1E 0.89 2.22 2.895(19) 132.2 1_565 yes
N5PA H5PD O1T 0.89 2.14 2.773(15) 127.2 2_666 yes
N5PA H5PE O1A 0.89 1.96 2.843(16) 169.8 . yes
N5PA H5PF O1T 0.89 2.14 2.851(15) 135.8 1_565 yes
N1PA H1PD O2B 0.89 1.93 2.802(14) 168.0 2_666 yes
N1PA H1PE O2W 0.89 1.99 2.867(10) 169.1 1_455 yes
N1PA H1PF O1W 0.89 1.97 2.772(16) 149.4 1_455 yes
O1T H1T O2A 0.82 2.09 2.763(5) 139.8 2_666 yes
O1W H1WA O1B 0.85 1.99 2.828(4) 170.4 . yes
O2W H2WB O2B 0.85 1.99 2.655(3) 134.4 1_565 yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cl1A C2A C3A C4A -179.1(2) . . . . ?
N1A C1A C2A Cl1A -2.2(3) . . . . ?
N1A C1A C2A C3A 177.7(3) . . . . ?
N1A C1A C6A Cl2A -1.3(3) . . . . ?
N1A C1A C6A C5A -179.6(2) . . . . ?
N1A C7A C8A C9A 178.5(2) . . . . ?
N1A C7A C12A C11A -179.1(2) . . . . ?
N1A C7A C12A C13A -0.8(4) . . . . ?
C1A N1A C7A C8A -16.7(4) . . . . ?
C1A N1A C7A C12A 163.2(2) . . . . ?
C1A C2A C3A C4A 1.1(4) . . . . ?
C2A C1A C6A Cl2A 174.37(18) . . . . ?
C2A C1A C6A C5A -3.9(4) . . . . ?
C2A C3A C4A C5A -2.4(4) . . . . ?
C3A C4A C5A C6A 0.5(4) . . . . ?
C4A C5A C6A C1A 2.8(4) . . . . ?
C4A C5A C6A Cl2A -175.5(2) . . . . ?
C6A C1A C2A Cl1A -177.89(18) . . . . ?
C6A C1A C2A C3A 1.9(4) . . . . ?
C7A N1A C1A C2A 130.3(3) . . . . ?
C7A N1A C1A C6A -54.3(4) . . . . ?
C7A C8A C9A C10A 1.0(4) . . . . ?
C7A C12A C13A C14A 76.2(3) . . . . ?
C8A C7A C12A C11A 0.7(4) . . . . ?
C8A C7A C12A C13A 179.1(2) . . . . ?
C8A C9A C10A C11A 0.2(4) . . . . ?
C9A C10A C11A C12A -0.8(5) . . . . ?
C10A C11A C12A C7A 0.4(4) . . . . ?
C10A C11A C12A C13A -178.0(3) . . . . ?
C11A C12A C13A C14A -105.5(3) . . . . ?
C12A C7A C8A C9A -1.4(4) . . . . ?
C12A C13A C14A O1A -39.0(4) . . . . ?
C12A C13A C14A O2A 137.9(4) . . . . ?
Cl1B C2B C3B C4B 175.7(2) . . . . ?
N1B C1B C2B Cl1B 2.6(3) . . . . ?
N1B C1B C2B C3B -179.2(2) . . . . ?
N1B C1B C6B Cl2B -0.9(3) . . . . ?
N1B C1B C6B C5B 180.0(2) . . . . ?
N1B C7B C8B C9B -178.1(2) . . . . ?
N1B C7B C12B C11B 178.4(2) . . . . ?
N1B C7B C12B C13B -0.2(4) . . . . ?
C1B N1B C7B C8B 16.8(4) . . . . ?
C1B N1B C7B C12B -163.3(2) . . . . ?
C1B C2B C3B C4B -2.5(4) . . . . ?
C2B C1B C6B Cl2B 174.63(17) . . . . ?
C2B C1B C6B C5B -4.5(4) . . . . ?
C2B C3B C4B C5B -1.5(4) . . . . ?
C3B C4B C5B C6B 2.3(4) . . . . ?
C4B C5B C6B C1B 0.9(4) . . . . ?
C4B C5B C6B Cl2B -178.3(2) . . . . ?
C6B C1B C2B Cl1B -172.81(18) . . . . ?
C6B C1B C2B C3B 5.4(3) . . . . ?
C7B N1B C1B C2B 51.4(4) . . . . ?
C7B N1B C1B C6B -133.5(3) . . . . ?
C7B C8B C9B C10B -0.5(4) . . . . ?
C7B C12B C13B C14B -77.4(3) . . . . ?
C8B C7B C12B C11B -1.6(4) . . . . ?
C8B C7B C12B C13B 179.7(2) . . . . ?
C8B C9B C10B C11B -1.4(4) . . . . ?
C9B C10B C11B C12B 1.8(5) . . . . ?
C10B C11B C12B C7B -0.3(4) . . . . ?
C10B C11B C12B C13B 178.4(3) . . . . ?
C11B C12B C13B C14B 104.0(3) . . . . ?
C12B C7B C8B C9B 2.0(4) . . . . ?
C12B C13B C14B O1B 45.9(4) . . . . ?
C12B C13B C14B O2B -135.7(3) . . . . ?
N1PB C2PB C3PB C4PB -64(2) . . . . ?
C2PB C3PB C4PB N5PB -96.4(15) . . . . ?
C2PA C3PA C4PA N5PA -168.4(9) . . . . ?
N1PA C2PA C3PA C4PA 69.0(12) . . . . ?

_olex2_exptl_crystal_mounting_method 
'coated in Paratone-N and mounted on a MiTeGen mount'
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.203
_oxdiff_exptl_absorpt_empirical_full_min 0.916
####################################################################### 
# 
# 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_exp_396_criproh_auto
_database_code_depnum_ccdc_archive 'CCDC 2245278'
loop_
_audit_author_name
_audit_author_address
'Christopher Richardson'
;University of Wollongong
Australia
;
_audit_update_record             
;
2024-05-14 deposited with the CCDC.	2024-05-23 downloaded from the CCDC.
;
_audit_creation_date             2024-05-14
_audit_creation_method           
;
Olex2 1.5
(compiled 2024.02.16 svn.r378c4104 for OlexSys, GUI svn.r6928)
;
_shelx_SHELXL_version_number     2017/1
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '2(C14 H10 Cl2 N O2), C3 H12 N2, 4(H2 O)'
_chemical_formula_sum            'C31 H40 Cl4 N4 O8'
_chemical_formula_weight         738.47
_chemical_absolute_configuration ad
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 1 21 1'
_space_group_name_Hall           'P 2yb'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'

_cell_length_a                   9.35740(10)
_cell_length_b                   36.5523(5)
_cell_length_c                   10.2282(2)
_cell_angle_alpha                90
_cell_angle_beta                 90.1340(10)
_cell_angle_gamma                90
_cell_volume                     3498.39(9)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    61150
_cell_measurement_temperature    295(1)
_cell_measurement_theta_max      29.8480
_cell_measurement_theta_min      1.9890
_shelx_estimated_absorpt_T_max   0.922
_shelx_estimated_absorpt_T_min   0.819
_exptl_absorpt_coefficient_mu    0.392
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94619
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.123a (Rigaku Oxford Diffraction, 2022)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.402
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             1544
_exptl_crystal_recrystallization_method 
'slow evaporation from isopropanol water'
_exptl_crystal_size_max          0.53
_exptl_crystal_size_mid          0.41
_exptl_crystal_size_min          0.21
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0286
_diffrn_reflns_av_unetI/netI     0.0238
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       51
_diffrn_reflns_limit_k_min       -51
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            155834
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.975
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.391
_diffrn_reflns_theta_min         1.991
_diffrn_ambient_temperature      295(1)
_diffrn_detector_area_resol_mean 10.0000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -74.00 110.00   0.50    7.00    --   20.00  54.00  27.68  368
  2  ω    -74.00 110.00   0.50    7.00    --   20.00  54.00 175.69  368
  3  ω    -74.00 110.00   0.50    7.00    --   20.00  54.00 -98.19  368
  4  ω    -74.00 110.00   0.50    7.00    --   20.00  54.00 109.71  368
  5  ω    -74.00 110.00   0.50    7.00    --   20.00  54.00 126.11  368
  6  ω    -74.00 110.00   0.50    7.00    --   20.00  54.00  42.96  368
  7  ω    -74.00 110.00   0.50    7.00    --   20.00  54.00-165.45  368
  8  ω     -6.00  84.00   0.50    7.00    --   20.00  54.00 -81.24  180
  9  ω     -6.00  84.00   0.50    7.00    --   20.00  54.00 -81.24  180
 10  ω     78.00 104.00   0.50    7.00    --   20.00  54.00 136.92   52
 11  ω    -49.00  83.00   0.50    7.00    --   20.00  54.00 150.00  264
 12  ω    -33.00  -8.00   0.50    7.00    --   20.00  54.00  60.00   50
 13  ω      4.00  30.00   0.50    7.00    --   20.00  54.00  60.00   52
 14  ω     48.00  74.00   0.50    7.00    --   20.00  54.00  60.00   52
 15  ω    -21.00  90.00   0.50    7.00    --   20.00  54.00  90.00  222
 16  ω     -7.00 110.00   0.50    7.00    --   20.00  54.00  32.87  234
 17  ω    -28.00 110.00   0.50    7.00    --   20.00  54.00 -62.26  276
 18  ω    -38.00 -13.00   0.50    7.00    --   20.00  54.00 -90.00   50
 19  ω     43.00  68.00   0.50    7.00    --   20.00  54.00 -90.00   50
 20  ω    -17.00   8.00   0.50    7.00    --   20.00  54.00-156.58   50
 21  ω     37.00  63.00   0.50    7.00    --   20.00  54.00-156.58   52
 22  ω     32.00  81.00   0.50    7.00    --   20.00  54.00 -30.00   98
 23  ω    -73.00 110.00   0.50    7.00    --   20.00  54.00 -10.32  366
 24  ω     79.00 105.00   0.50    7.00    --   20.00  54.00  76.02   52
 25  ω    -73.00 110.00   0.50    7.00    --   20.00  54.00  16.06  366
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini II'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.954
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.965
_reflns_number_gt                16914
_reflns_number_total             20631
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_collection       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_molecular_graphics    'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2017/1 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.186
_refine_diff_density_min         -0.343
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details 
;
 Flack x determined using 7228 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.027(7)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     972
_refine_ls_number_reflns         20631
_refine_ls_number_restraints     4
_refine_ls_R_factor_all          0.0474
_refine_ls_R_factor_gt           0.0336
_refine_ls_restrained_S_all      1.029
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0402P)²+0.3664P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0756
_refine_ls_wR_factor_ref         0.0810
_refine_special_details          
;
Water molecule based on O4W positioned its H atoms to no H-bond acceptors 
with AFIX and a convergent refinement. Manual positioning to give a H-bond 
with O2D (+X +Y -1+Z) did not work (back to position of unconstrained 
refinement for H atoms). Therefore, the atomic coordinates were fixed for all 
the atoms using the refined position for the O atom and positioning H4WA to 
give a H-bond contact with O2D (H4WA...O2D 1.95 Ang) and not positioning 
H4WB unappropriately close to hydrogens on O5W. The best position, in our 
view, was to point H4WB into a cavity where it makes no H-bonds. There are 
no other acceptors with appropriate distances.
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.5 times of:
  All O(H,H) groups
2. Restrained distances
 N1D-H1D = N1C-H1C = N1B-H1B = N1A-H1A
 0.85 with sigma of 0.02
3. Others
 Sof(O8WA)=Sof(H8WA)=Sof(H8WB)=1-FVAR(1)
 Sof(O8WB)=Sof(H8WC)=Sof(H8WD)=FVAR(1)
 Fixed X: O4W(0.76706) H4WA(0.72742) H4WB(0.853361)
 Fixed Y: O4W(0.55293) H4WA(0.55583) H4WB(0.55932)
 Fixed Z: O4W(0.02495) H4WA(-0.04918) H4WB(0.01296)
4.a Free rotating group:
 O6W(H6WA,H6WB), O3W(H3WA,H3WB), O5W(H5WA,H5WB), O8WA(H8WA,H8WB), O1W(H1WA,
 H1WB), O7W(H7WA,H7WB), O2W(H2WA,H2WB), O8WB(H8WC,H8WD)
4.b Secondary CH2 refined with riding coordinates:
 C13C(H13A,H13B), C13D(H13C,H13D), C13A(H13E,H13F), C13B(H13G,H13H), C2P(H2PA,
 H2PB), C3P(H3PA,H3PB), C4P(H4PA,H4PB), C2N(H2NA,H2NB), C3N(H3NA,H3NB),
 C4N(H4NA,H4NB)
4.c Aromatic/amide H refined with riding coordinates:
 C3C(H3C), C4C(H4C), C5C(H5C), C8C(H8C), C9C(H9C), C10C(H10C), C11C(H11C),
 C3D(H3D), C4D(H4D), C5D(H5D), C8D(H8D), C9D(H9D), C10D(H10D), C11D(H11D),
 C3A(H3A), C4A(H4A), C5A(H5A), C8A(H8A), C9A(H9A), C10A(H10A), C11A(H11A),
 C3B(H3B), C4B(H4B), C5B(H5B), C8B(H8B), C9B(H9B), C10B(H10B), C11B(H11B)
4.d Idealised Me refined as rotating group:
 N1P(H1PA,H1PB,H1PC), N5P(H5PA,H5PB,H5PC), N1N(H1NA,H1NB,H1NC), N5N(H5NA,H5NB,
 H5NC)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1C Cl 0.19583(7) 0.73276(8) 1.08406(6) 0.04288(14) Uani 1 1 d . . . . .
O1C O 0.0634(2) 0.54414(9) 1.17242(18) 0.0521(5) Uani 1 1 d . . . . .
N1C N 0.2283(2) 0.65213(9) 1.0114(2) 0.0350(4) Uani 1 1 d D . . . .
H1C H 0.258(3) 0.6301(6) 1.008(2) 0.030(6) Uiso 1 1 d D . . . .
C1C C 0.3124(2) 0.67695(10) 0.9423(2) 0.0306(4) Uani 1 1 d . . . . .
C2C C 0.3055(2) 0.71502(10) 0.9634(2) 0.0326(5) Uani 1 1 d . . . . .
O2C O 0.2068(2) 0.57449(9) 1.0399(2) 0.0522(5) Uani 1 1 d . . . . .
Cl2C Cl 0.44424(7) 0.61871(8) 0.83109(8) 0.05215(16) Uani 1 1 d . . . . .
C3C C 0.3872(3) 0.73953(10) 0.8920(3) 0.0412(6) Uani 1 1 d . . . . .
H3C H 0.376996 0.764551 0.905540 0.046(8) Uiso 1 1 calc R . . . .
C4C C 0.4836(3) 0.72677(11) 0.8007(3) 0.0462(6) Uani 1 1 d . . . . .
H4C H 0.536530 0.743172 0.750927 0.058(9) Uiso 1 1 calc R . . . .
C5C C 0.5011(3) 0.68955(11) 0.7835(3) 0.0426(6) Uani 1 1 d . . . . .
H5C H 0.569071 0.680789 0.725218 0.055(9) Uiso 1 1 calc R . . . .
C6C C 0.4169(2) 0.66534(10) 0.8535(2) 0.0349(5) Uani 1 1 d . . . . .
C7C C 0.0777(2) 0.65515(9) 1.0210(2) 0.0296(4) Uani 1 1 d . . . . .
C8C C -0.0020(3) 0.67735(10) 0.9375(2) 0.0343(5) Uani 1 1 d . . . . .
H8C H 0.043869 0.690268 0.871396 0.035(7) Uiso 1 1 calc R . . . .
C9C C -0.1491(3) 0.68042(10) 0.9517(3) 0.0399(6) Uani 1 1 d . . . . .
H9C H -0.201149 0.695529 0.896091 0.035(7) Uiso 1 1 calc R . . . .
C10C C -0.2175(3) 0.66107(11) 1.0483(3) 0.0467(6) Uani 1 1 d . . . . .
H10C H -0.315780 0.663376 1.059131 0.050(8) Uiso 1 1 calc R . . . .
C11C C -0.1399(3) 0.63815(10) 1.1294(3) 0.0419(6) Uani 1 1 d . . . . .
H11C H -0.187474 0.624834 1.193476 0.052(9) Uiso 1 1 calc R . . . .
C12C C 0.0079(3) 0.63452(10) 1.1175(2) 0.0333(5) Uani 1 1 d . . . . .
C13C C 0.0897(3) 0.60885(10) 1.2054(2) 0.0391(5) Uani 1 1 d . . . . .
H13A H 0.033867 0.603810 1.283126 0.058(9) Uiso 1 1 calc R . . . .
H13B H 0.178334 0.620373 1.232572 0.038(7) Uiso 1 1 calc R . . . .
C14C C 0.1229(3) 0.57303(10) 1.1353(2) 0.0355(5) Uani 1 1 d . . . . .
O1D O 0.77290(18) 0.56774(9) 0.55785(17) 0.0377(4) Uani 1 1 d . . . . .
N1D N 0.7380(2) 0.64819(9) 0.5151(2) 0.0359(4) Uani 1 1 d D . . . .
H1D H 0.709(3) 0.6261(6) 0.505(3) 0.037(7) Uiso 1 1 d D . . . .
Cl1D Cl 0.78932(7) 0.72846(8) 0.58911(6) 0.04357(14) Uani 1 1 d . . . . .
C1D C 0.6628(2) 0.67444(10) 0.4450(2) 0.0312(4) Uani 1 1 d . . . . .
Cl2D Cl 0.53075(7) 0.61828(8) 0.31873(7) 0.04936(16) Uani 1 1 d . . . . .
O2D O 0.7051(2) 0.55546(9) 0.76125(19) 0.0477(5) Uani 1 1 d . . . . .
C2D C 0.6749(3) 0.71222(10) 0.4682(2) 0.0333(5) Uani 1 1 d . . . . .
C3D C 0.5971(3) 0.73800(10) 0.3990(3) 0.0416(6) Uani 1 1 d . . . . .
H3D H 0.610873 0.762804 0.414793 0.062(10) Uiso 1 1 calc R . . . .
C4D C 0.4992(3) 0.72678(11) 0.3066(3) 0.0454(6) Uani 1 1 d . . . . .
H4D H 0.447381 0.744021 0.259345 0.070(11) Uiso 1 1 calc R . . . .
C5D C 0.4779(3) 0.68986(11) 0.2842(3) 0.0419(6) Uani 1 1 d . . . . .
H5D H 0.409846 0.682172 0.223751 0.048(8) Uiso 1 1 calc R . . . .
C6D C 0.5581(3) 0.66455(10) 0.3521(2) 0.0339(5) Uani 1 1 d . . . . .
C7D C 0.8890(2) 0.64862(10) 0.5333(2) 0.0300(4) Uani 1 1 d . . . . .
C8D C 0.9770(3) 0.66887(10) 0.4509(3) 0.0381(5) Uani 1 1 d . . . . .
H8D H 0.937707 0.681715 0.381007 0.045(8) Uiso 1 1 calc R . . . .
C9D C 1.1237(3) 0.66985(11) 0.4731(3) 0.0450(6) Uani 1 1 d . . . . .
H9D H 1.182584 0.683418 0.418254 0.055(9) Uiso 1 1 calc R . . . .
C10D C 1.1819(3) 0.65061(11) 0.5768(3) 0.0477(7) Uani 1 1 d . . . . .
H10D H 1.279731 0.651559 0.592836 0.082(12) Uiso 1 1 calc R . . . .
C11D C 1.0944(3) 0.63001(10) 0.6565(3) 0.0399(5) Uani 1 1 d . . . . .
H11D H 1.134829 0.616824 0.725010 0.039(7) Uiso 1 1 calc R . . . .
C12D C 0.9460(2) 0.62842(9) 0.6370(2) 0.0305(4) Uani 1 1 d . . . . .
C13D C 0.8532(3) 0.60745(10) 0.7305(2) 0.0341(5) Uani 1 1 d . . . . .
H13C H 0.783341 0.624328 0.766043 0.043(7) Uiso 1 1 calc R . . . .
H13D H 0.912950 0.599457 0.802690 0.044(8) Uiso 1 1 calc R . . . .
C14D C 0.7728(2) 0.57411(10) 0.6790(2) 0.0313(4) Uani 1 1 d . . . . .
Cl1A Cl 0.04819(7) 0.37910(8) 0.70272(7) 0.04704(15) Uani 1 1 d . . . . .
C1A C 0.1851(2) 0.32330(10) 0.8268(2) 0.0314(4) Uani 1 1 d . . . . .
O1A O 0.2473(2) 0.44818(9) 1.1071(2) 0.0477(4) Uani 1 1 d . . . . .
N1A N 0.2640(2) 0.34984(9) 0.8927(2) 0.0367(4) Uani 1 1 d D . . . .
H1A H 0.230(3) 0.3724(6) 0.886(3) 0.036(7) Uiso 1 1 d D . . . .
O2A O 0.3103(3) 0.42883(9) 0.9103(2) 0.0624(6) Uani 1 1 d . . . . .
Cl2A Cl 0.30993(7) 0.27030(8) 0.97561(7) 0.04441(14) Uani 1 1 d . . . . .
C2A C 0.0796(2) 0.33285(10) 0.7353(2) 0.0332(5) Uani 1 1 d . . . . .
C3A C -0.0029(3) 0.30740(11) 0.6691(2) 0.0398(6) Uani 1 1 d . . . . .
H3A H -0.071707 0.314967 0.609180 0.047(8) Uiso 1 1 calc R . . . .
C4A C 0.0185(3) 0.27052(11) 0.6932(3) 0.0444(6) Uani 1 1 d . . . . .
H4A H -0.033800 0.253085 0.647286 0.060(9) Uiso 1 1 calc R . . . .
C5A C 0.1178(3) 0.25967(10) 0.7859(3) 0.0408(6) Uani 1 1 d . . . . .
H5A H 0.131545 0.234933 0.803181 0.048(8) Uiso 1 1 calc R . . . .
C6A C 0.1968(2) 0.28571(10) 0.8528(2) 0.0336(5) Uani 1 1 d . . . . .
C7A C 0.4151(2) 0.34882(10) 0.9079(2) 0.0323(5) Uani 1 1 d . . . . .
C8A C 0.5018(3) 0.32752(10) 0.8278(3) 0.0370(5) Uani 1 1 d . . . . .
H8A H 0.460933 0.313737 0.761054 0.050(9) Uiso 1 1 calc R . . . .
C9A C 0.6485(3) 0.32671(11) 0.8468(3) 0.0452(6) Uani 1 1 d . . . . .
H9A H 0.705588 0.312004 0.794211 0.048(8) Uiso 1 1 calc R . . . .
C10A C 0.7098(3) 0.34783(11) 0.9442(3) 0.0509(7) Uani 1 1 d . . . . .
H10A H 0.808212 0.347499 0.956817 0.058(9) Uiso 1 1 calc R . . . .
C11A C 0.6240(3) 0.36946(11) 1.0227(3) 0.0440(6) Uani 1 1 d . . . . .
H11A H 0.666171 0.383597 1.087806 0.058(9) Uiso 1 1 calc R . . . .
C12A C 0.4757(2) 0.37057(10) 1.0065(2) 0.0332(5) Uani 1 1 d . . . . .
C13A C 0.3851(3) 0.39356(10) 1.0954(3) 0.0389(5) Uani 1 1 d . . . . .
H13E H 0.445279 0.402919 1.165127 0.051(8) Uiso 1 1 calc R . . . .
H13F H 0.313580 0.377925 1.135166 0.043(8) Uiso 1 1 calc R . . . .
C14A C 0.3087(3) 0.42593(10) 1.0307(3) 0.0391(5) Uani 1 1 d . . . . .
O1AB O 0.5760(3) 0.45793(9) 0.5712(2) 0.0549(5) Uani 1 1 d . . . . .
O2AB O 0.7439(2) 0.43000(9) 0.4554(2) 0.0535(5) Uani 1 1 d . . . . .
N1B N 0.7488(2) 0.35115(9) 0.4071(2) 0.0361(4) Uani 1 1 d D . . . .
H1B H 0.782(3) 0.3728(7) 0.408(3) 0.047(8) Uiso 1 1 d D . . . .
C1B C 0.8310(2) 0.32634(10) 0.3369(2) 0.0307(4) Uani 1 1 d . . . . .
Cl1B Cl 0.71220(7) 0.26999(8) 0.47390(6) 0.04327(14) Uani 1 1 d . . . . .
C2B C 0.8229(2) 0.28823(10) 0.3547(2) 0.0330(5) Uani 1 1 d . . . . .
Cl2B Cl 0.96250(8) 0.38484(8) 0.22771(8) 0.05267(17) Uani 1 1 d . . . . .
C3B C 0.9043(3) 0.26388(10) 0.2825(3) 0.0413(6) Uani 1 1 d . . . . .
H3B H 0.893808 0.238816 0.294844 0.050(8) Uiso 1 1 calc R . . . .
C4B C 1.0008(3) 0.27690(11) 0.1924(3) 0.0483(7) Uani 1 1 d . . . . .
H4B H 1.053902 0.260598 0.142328 0.085(12) Uiso 1 1 calc R . . . .
C5B C 1.0191(3) 0.31417(11) 0.1761(3) 0.0439(6) Uani 1 1 d . . . . .
H5B H 1.086966 0.323057 0.117927 0.055(9) Uiso 1 1 calc R . . . .
C6B C 0.9352(2) 0.33807(10) 0.2473(2) 0.0352(5) Uani 1 1 d . . . . .
C7B C 0.5978(2) 0.34903(10) 0.4164(2) 0.0310(4) Uani 1 1 d . . . . .
C8B C 0.5177(3) 0.32748(10) 0.3311(3) 0.0375(5) Uani 1 1 d . . . . .
H8B H 0.563276 0.314762 0.264377 0.045(8) Uiso 1 1 calc R . . . .
C9B C 0.3711(3) 0.32478(11) 0.3445(3) 0.0447(6) Uani 1 1 d . . . . .
H9B H 0.318926 0.309882 0.288265 0.048(8) Uiso 1 1 calc R . . . .
C10B C 0.3019(3) 0.34424(11) 0.4416(3) 0.0489(7) Uani 1 1 d . . . . .
H10B H 0.203359 0.342368 0.451273 0.077(12) Uiso 1 1 calc R . . . .
C11B C 0.3807(3) 0.36653(11) 0.5244(3) 0.0431(6) Uani 1 1 d . . . . .
H11B H 0.333708 0.379941 0.588529 0.045(8) Uiso 1 1 calc R . . . .
C12B C 0.5292(3) 0.36931(10) 0.5136(2) 0.0332(5) Uani 1 1 d . . . . .
C13B C 0.6107(3) 0.39425(10) 0.6061(2) 0.0366(5) Uani 1 1 d . . . . .
H13G H 0.698399 0.382353 0.633621 0.058(9) Uiso 1 1 calc R . . . .
H13H H 0.553447 0.398913 0.683222 0.047(8) Uiso 1 1 calc R . . . .
C14B C 0.6461(3) 0.43040(10) 0.5389(2) 0.0369(5) Uani 1 1 d . . . . .
N1P N 0.5388(2) 0.52793(9) 0.47598(19) 0.0356(4) Uani 1 1 d . . . . .
H1PA H 0.540040 0.530131 0.389328 0.047(8) Uiso 1 1 calc R . . . .
H1PB H 0.545192 0.504394 0.497548 0.040(7) Uiso 1 1 calc R . . . .
H1PC H 0.612426 0.540069 0.510081 0.047(8) Uiso 1 1 calc R . . . .
C2P C 0.4030(3) 0.54329(10) 0.5277(2) 0.0382(5) Uani 1 1 d . . . . .
H2PA H 0.407148 0.569788 0.524809 0.054(9) Uiso 1 1 calc R . . . .
H2PB H 0.391657 0.535984 0.618308 0.052(8) Uiso 1 1 calc R . . . .
C3P C 0.2763(3) 0.53024(11) 0.4497(3) 0.0402(5) Uani 1 1 d . . . . .
H3PA H 0.269170 0.503818 0.455877 0.055(9) Uiso 1 1 calc R . . . .
H3PB H 0.289172 0.536609 0.358406 0.052(8) Uiso 1 1 calc R . . . .
C4P C 0.1397(3) 0.54753(10) 0.5002(2) 0.0389(5) Uani 1 1 d . . . . .
H4PA H 0.132130 0.543145 0.593486 0.053(8) Uiso 1 1 calc R . . . .
H4PB H 0.143790 0.573776 0.486625 0.057(9) Uiso 1 1 calc R . . . .
N5P N 0.0108(2) 0.53260(10) 0.4335(2) 0.0388(4) Uani 1 1 d . . . . .
H5PA H 0.016667 0.536929 0.348069 0.071(11) Uiso 1 1 calc R . . . .
H5PB H -0.067036 0.543341 0.465369 0.044(8) Uiso 1 1 calc R . . . .
H5PC H 0.005715 0.508588 0.447203 0.063(10) Uiso 1 1 calc R . . . .
N1N N 0.9739(2) 0.47518(10) 1.0354(2) 0.0424(5) Uani 1 1 d . . . . .
H1NA H 0.984047 0.496860 0.996909 0.057(9) Uiso 1 1 calc R . . . .
H1NB H 1.057856 0.467907 1.067244 0.059(9) Uiso 1 1 calc R . . . .
H1NC H 0.911153 0.477033 1.100305 0.071(11) Uiso 1 1 calc R . . . .
C2N C 0.9218(3) 0.44804(11) 0.9382(3) 0.0474(6) Uani 1 1 d . . . . .
H2NA H 0.881657 0.427250 0.984244 0.059(9) Uiso 1 1 calc R . . . .
H2NB H 1.002172 0.439315 0.887245 0.053(9) Uiso 1 1 calc R . . . .
C3N C 0.8096(3) 0.46347(11) 0.8460(3) 0.0455(6) Uani 1 1 d . . . . .
H3NA H 0.844231 0.486397 0.810386 0.061(10) Uiso 1 1 calc R . . . .
H3NB H 0.796466 0.446613 0.773754 0.077(11) Uiso 1 1 calc R . . . .
C4N C 0.6667(3) 0.47006(11) 0.9104(3) 0.0413(5) Uani 1 1 d . . . . .
H4NA H 0.624528 0.446796 0.934674 0.062(10) Uiso 1 1 calc R . . . .
H4NB H 0.680530 0.484268 0.989552 0.049(8) Uiso 1 1 calc R . . . .
N5N N 0.5675(2) 0.49002(9) 0.8206(2) 0.0367(4) Uani 1 1 d . . . . .
H5NA H 0.549213 0.476203 0.750946 0.047(8) Uiso 1 1 calc R . . . .
H5NB H 0.608044 0.510866 0.795216 0.047(8) Uiso 1 1 calc R . . . .
H5NC H 0.486324 0.494889 0.862262 0.046(8) Uiso 1 1 calc R . . . .
O6W O 0.0209(3) 0.45806(10) 0.5142(2) 0.0594(5) Uani 1 1 d G . . . .
H6WA H 0.079971 0.449860 0.458289 0.081(14) Uiso 1 1 d G . . . .
H6WB H -0.059778 0.450038 0.488400 0.112(18) Uiso 1 1 d G . . . .
O3W O 0.3697(2) 0.51327(9) 0.0176(2) 0.0448(4) Uani 1 1 d G . . . .
H3WA H 0.324118 0.533366 0.020154 0.077(12) Uiso 1 1 d G . . . .
H3WB H 0.313609 0.497826 0.052590 0.076(12) Uiso 1 1 d G . . . .
O5W O 0.5704(2) 0.53089(10) 0.20342(19) 0.0549(5) Uani 1 1 d G . . . .
H5WA H 0.634600 0.541264 0.157901 0.062(10) Uiso 1 1 d G . . . .
H5WB H 0.507936 0.524086 0.148031 0.058(10) Uiso 1 1 d G . . . .
O8WA O 0.762(4) 0.4694(13) 0.227(3) 0.090(8) Uani 0.45(6) 1 d G . P A 2
H8WA H 0.777548 0.485998 0.283592 0.134 Uiso 0.45(6) 1 d G U P A 2
H8WB H 0.675409 0.463290 0.239276 0.134 Uiso 0.45(6) 1 d G U P A 2
O4W O 0.767060 0.552930 0.024950 0.0838(9) Uani 1 1 d . . . . .
H4WA H 0.727420 0.555830 -0.049180 0.126 Uiso 1 1 d . U . . .
H4WB H 0.853361 0.559320 0.012960 0.126 Uiso 1 1 d . U . . .
O1W O 0.2252(3) 0.47811(10) 0.7273(2) 0.0673(6) Uani 1 1 d G . . . .
H1WA H 0.258220 0.461488 0.777120 0.081(13) Uiso 1 1 d G . . . .
H1WB H 0.187215 0.466538 0.664244 0.102(16) Uiso 1 1 d G . . . .
O7W O 0.2519(3) 0.43909(11) 0.3728(3) 0.0756(7) Uani 1 1 d G . . . .
H7WA H 0.271159 0.442062 0.292355 0.12(2) Uiso 1 1 d G . . . .
H7WB H 0.322517 0.427075 0.403051 0.18(3) Uiso 1 1 d G . . . .
O2W O 0.0624(3) 0.53206(11) 0.8477(2) 0.0644(6) Uani 1 1 d G . . . .
H2WA H 0.123198 0.518713 0.808700 0.087(14) Uiso 1 1 d G . . . .
H2WB H 0.112738 0.546934 0.892259 0.088(14) Uiso 1 1 d G . . . .
O8WB O 0.7957(12) 0.4807(4) 0.2601(19) 0.055(3) Uani 0.55(6) 1 d G . P A 1
H8WC H 0.769847 0.462687 0.306587 0.028(16) Uiso 0.55(6) 1 d G . P A 1
H8WD H 0.720301 0.493448 0.250697 0.05(2) Uiso 0.55(6) 1 d G . P A 1


_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
Cl1C C2C 1.733(2) . ?
O1C C14C 1.253(3) . ?
N1C H1C 0.85(2) . ?
N1C C1C 1.394(3) . ?
N1C C7C 1.417(3) . ?
C1C C2C 1.409(3) . ?
C1C C6C 1.402(3) . ?
C2C C3C 1.387(3) . ?
O2C C14C 1.255(3) . ?
Cl2C C6C 1.739(3) . ?
C3C H3C 0.9300 . ?
C3C C4C 1.381(4) . ?
C4C H4C 0.9300 . ?
C4C C5C 1.381(4) . ?
C5C H5C 0.9300 . ?
C5C C6C 1.385(4) . ?
C7C C8C 1.393(3) . ?
C7C C12C 1.404(3) . ?
C8C H8C 0.9300 . ?
C8C C9C 1.389(3) . ?
C9C H9C 0.9300 . ?
C9C C10C 1.375(4) . ?
C10C H10C 0.9300 . ?
C10C C11C 1.384(4) . ?
C11C H11C 0.9300 . ?
C11C C12C 1.395(4) . ?
C12C C13C 1.508(3) . ?
C13C H13A 0.9700 . ?
C13C H13B 0.9700 . ?
C13C C14C 1.525(3) . ?
O1D C14D 1.261(3) . ?
N1D H1D 0.86(2) . ?
N1D C1D 1.389(3) . ?
N1D C7D 1.425(3) . ?
Cl1D C2D 1.738(2) . ?
C1D C2D 1.406(3) . ?
C1D C6D 1.410(3) . ?
Cl2D C6D 1.744(3) . ?
O2D C14D 1.255(3) . ?
C2D C3D 1.385(3) . ?
C3D H3D 0.9300 . ?
C3D C4D 1.377(4) . ?
C4D H4D 0.9300 . ?
C4D C5D 1.383(4) . ?
C5D H5D 0.9300 . ?
C5D C6D 1.378(4) . ?
C7D C8D 1.393(3) . ?
C7D C12D 1.397(3) . ?
C8D H8D 0.9300 . ?
C8D C9D 1.392(4) . ?
C9D H9D 0.9300 . ?
C9D C10D 1.384(4) . ?
C10D H10D 0.9300 . ?
C10D C11D 1.380(4) . ?
C11D H11D 0.9300 . ?
C11D C12D 1.403(3) . ?
C12D C13D 1.504(3) . ?
C13D H13C 0.9700 . ?
C13D H13D 0.9700 . ?
C13D C14D 1.525(3) . ?
Cl1A C2A 1.748(2) . ?
C1A N1A 1.392(3) . ?
C1A C2A 1.403(3) . ?
C1A C6A 1.404(3) . ?
O1A C14A 1.267(3) . ?
N1A H1A 0.89(2) . ?
N1A C7A 1.423(3) . ?
O2A C14A 1.236(3) . ?
Cl2A C6A 1.735(2) . ?
C2A C3A 1.384(3) . ?
C3A H3A 0.9300 . ?
C3A C4A 1.385(4) . ?
C4A H4A 0.9300 . ?
C4A C5A 1.384(4) . ?
C5A H5A 0.9300 . ?
C5A C6A 1.385(3) . ?
C7A C8A 1.392(3) . ?
C7A C12A 1.402(3) . ?
C8A H8A 0.9300 . ?
C8A C9A 1.387(4) . ?
C9A H9A 0.9300 . ?
C9A C10A 1.383(4) . ?
C10A H10A 0.9300 . ?
C10A C11A 1.384(4) . ?
C11A H11A 0.9300 . ?
C11A C12A 1.398(3) . ?
C12A C13A 1.502(3) . ?
C13A H13E 0.9700 . ?
C13A H13F 0.9700 . ?
C13A C14A 1.532(3) . ?
O1AB C14B 1.246(3) . ?
O2AB C14B 1.253(3) . ?
N1B H1B 0.85(2) . ?
N1B C1B 1.390(3) . ?
N1B C7B 1.418(3) . ?
C1B C2B 1.407(3) . ?
C1B C6B 1.407(3) . ?
Cl1B C2B 1.735(3) . ?
C2B C3B 1.386(3) . ?
Cl2B C6B 1.740(3) . ?
C3B H3B 0.9300 . ?
C3B C4B 1.377(4) . ?
C4B H4B 0.9300 . ?
C4B C5B 1.383(4) . ?
C5B H5B 0.9300 . ?
C5B C6B 1.383(4) . ?
C7B C8B 1.393(3) . ?
C7B C12B 1.397(3) . ?
C8B H8B 0.9300 . ?
C8B C9B 1.382(4) . ?
C9B H9B 0.9300 . ?
C9B C10B 1.383(4) . ?
C10B H10B 0.9300 . ?
C10B C11B 1.386(4) . ?
C11B H11B 0.9300 . ?
C11B C12B 1.399(4) . ?
C12B C13B 1.518(3) . ?
C13B H13G 0.9700 . ?
C13B H13H 0.9700 . ?
C13B C14B 1.526(3) . ?
N1P H1PA 0.8900 . ?
N1P H1PB 0.8900 . ?
N1P H1PC 0.8900 . ?
N1P C2P 1.488(3) . ?
C2P H2PA 0.9700 . ?
C2P H2PB 0.9700 . ?
C2P C3P 1.506(3) . ?
C3P H3PA 0.9700 . ?
C3P H3PB 0.9700 . ?
C3P C4P 1.518(4) . ?
C4P H4PA 0.9700 . ?
C4P H4PB 0.9700 . ?
C4P N5P 1.488(3) . ?
N5P H5PA 0.8900 . ?
N5P H5PB 0.8900 . ?
N5P H5PC 0.8900 . ?
N1N H1NA 0.8900 . ?
N1N H1NB 0.8900 . ?
N1N H1NC 0.8900 . ?
N1N C2N 1.486(4) . ?
C2N H2NA 0.9700 . ?
C2N H2NB 0.9700 . ?
C2N C3N 1.518(4) . ?
C3N H3NA 0.9700 . ?
C3N H3NB 0.9700 . ?
C3N C4N 1.511(4) . ?
C4N H4NA 0.9700 . ?
C4N H4NB 0.9700 . ?
C4N N5N 1.494(3) . ?
N5N H5NA 0.8900 . ?
N5N H5NB 0.8900 . ?
N5N H5NC 0.8900 . ?
O6W H6WA 0.8513 . ?
O6W H6WB 0.8509 . ?
O3W H3WA 0.8500 . ?
O3W H3WB 0.8503 . ?
O5W H5WA 0.8503 . ?
O5W H5WB 0.8500 . ?
O8WA H8WA 0.8499 . ?
O8WA H8WB 0.8499 . ?
O4W H4WA 0.849944(16) . ?
O4W H4WB 0.849826(17) . ?
O1W H1WA 0.8505 . ?
O1W H1WB 0.8487 . ?
O7W H7WA 0.8498 . ?
O7W H7WB 0.8511 . ?
O2W H2WA 0.8496 . ?
O2W H2WB 0.8513 . ?
O8WB H8WC 0.8489 . ?
O8WB H8WD 0.8503 . ?

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
C1C N1C H1C 114.3(17) . . ?
C1C N1C C7C 123.14(19) . . ?
C7C N1C H1C 113.5(18) . . ?
N1C C1C C2C 122.6(2) . . ?
N1C C1C C6C 121.8(2) . . ?
C6C C1C C2C 115.5(2) . . ?
C1C C2C Cl1C 120.37(18) . . ?
C3C C2C Cl1C 117.47(19) . . ?
C3C C2C C1C 122.1(2) . . ?
C2C C3C H3C 120.0 . . ?
C4C C3C C2C 120.0(2) . . ?
C4C C3C H3C 120.0 . . ?
C3C C4C H4C 120.1 . . ?
C3C C4C C5C 119.7(2) . . ?
C5C C4C H4C 120.1 . . ?
C4C C5C H5C 120.1 . . ?
C4C C5C C6C 119.7(2) . . ?
C6C C5C H5C 120.1 . . ?
C1C C6C Cl2C 119.03(19) . . ?
C5C C6C C1C 122.7(2) . . ?
C5C C6C Cl2C 118.3(2) . . ?
C8C C7C N1C 122.2(2) . . ?
C8C C7C C12C 119.7(2) . . ?
C12C C7C N1C 118.1(2) . . ?
C7C C8C H8C 119.6 . . ?
C9C C8C C7C 120.8(2) . . ?
C9C C8C H8C 119.6 . . ?
C8C C9C H9C 120.1 . . ?
C10C C9C C8C 119.8(2) . . ?
C10C C9C H9C 120.1 . . ?
C9C C10C H10C 120.1 . . ?
C9C C10C C11C 119.9(2) . . ?
C11C C10C H10C 120.1 . . ?
C10C C11C H11C 119.2 . . ?
C10C C11C C12C 121.6(2) . . ?
C12C C11C H11C 119.2 . . ?
C7C C12C C13C 121.2(2) . . ?
C11C C12C C7C 118.2(2) . . ?
C11C C12C C13C 120.6(2) . . ?
C12C C13C H13A 109.5 . . ?
C12C C13C H13B 109.4 . . ?
C12C C13C C14C 110.9(2) . . ?
H13A C13C H13B 108.0 . . ?
C14C C13C H13A 109.4 . . ?
C14C C13C H13B 109.5 . . ?
O1C C14C O2C 123.4(2) . . ?
O1C C14C C13C 119.3(2) . . ?
O2C C14C C13C 117.2(2) . . ?
C1D N1D H1D 115.5(19) . . ?
C1D N1D C7D 124.15(19) . . ?
C7D N1D H1D 109.8(18) . . ?
N1D C1D C2D 123.4(2) . . ?
N1D C1D C6D 121.4(2) . . ?
C2D C1D C6D 114.9(2) . . ?
C1D C2D Cl1D 120.33(18) . . ?
C3D C2D Cl1D 117.00(19) . . ?
C3D C2D C1D 122.7(2) . . ?
C2D C3D H3D 120.1 . . ?
C4D C3D C2D 119.8(2) . . ?
C4D C3D H3D 120.1 . . ?
C3D C4D H4D 120.0 . . ?
C3D C4D C5D 120.0(2) . . ?
C5D C4D H4D 120.0 . . ?
C4D C5D H5D 120.2 . . ?
C6D C5D C4D 119.6(2) . . ?
C6D C5D H5D 120.2 . . ?
C1D C6D Cl2D 118.78(18) . . ?
C5D C6D C1D 123.0(2) . . ?
C5D C6D Cl2D 118.25(19) . . ?
C8D C7D N1D 120.9(2) . . ?
C8D C7D C12D 121.0(2) . . ?
C12D C7D N1D 118.1(2) . . ?
C7D C8D H8D 120.0 . . ?
C9D C8D C7D 120.0(2) . . ?
C9D C8D H8D 120.0 . . ?
C8D C9D H9D 120.1 . . ?
C10D C9D C8D 119.9(3) . . ?
C10D C9D H9D 120.1 . . ?
C9D C10D H10D 120.1 . . ?
C11D C10D C9D 119.8(2) . . ?
C11D C10D H10D 120.1 . . ?
C10D C11D H11D 119.1 . . ?
C10D C11D C12D 121.8(2) . . ?
C12D C11D H11D 119.1 . . ?
C7D C12D C11D 117.6(2) . . ?
C7D C12D C13D 122.1(2) . . ?
C11D C12D C13D 120.2(2) . . ?
C12D C13D H13C 107.8 . . ?
C12D C13D H13D 107.8 . . ?
C12D C13D C14D 118.21(19) . . ?
H13C C13D H13D 107.1 . . ?
C14D C13D H13C 107.8 . . ?
C14D C13D H13D 107.8 . . ?
O1D C14D C13D 119.0(2) . . ?
O2D C14D O1D 124.1(2) . . ?
O2D C14D C13D 116.9(2) . . ?
N1A C1A C2A 121.4(2) . . ?
N1A C1A C6A 123.3(2) . . ?
C2A C1A C6A 115.1(2) . . ?
C1A N1A H1A 114.9(18) . . ?
C1A N1A C7A 124.1(2) . . ?
C7A N1A H1A 112.9(18) . . ?
C1A C2A Cl1A 119.04(18) . . ?
C3A C2A Cl1A 117.62(19) . . ?
C3A C2A C1A 123.3(2) . . ?
C2A C3A H3A 120.4 . . ?
C2A C3A C4A 119.1(2) . . ?
C4A C3A H3A 120.4 . . ?
C3A C4A H4A 120.1 . . ?
C5A C4A C3A 119.8(2) . . ?
C5A C4A H4A 120.1 . . ?
C4A C5A H5A 120.1 . . ?
C4A C5A C6A 119.9(2) . . ?
C6A C5A H5A 120.1 . . ?
C1A C6A Cl2A 120.14(19) . . ?
C5A C6A C1A 122.5(2) . . ?
C5A C6A Cl2A 117.31(19) . . ?
C8A C7A N1A 122.0(2) . . ?
C8A C7A C12A 120.3(2) . . ?
C12A C7A N1A 117.6(2) . . ?
C7A C8A H8A 119.8 . . ?
C9A C8A C7A 120.5(2) . . ?
C9A C8A H8A 119.8 . . ?
C8A C9A H9A 120.1 . . ?
C10A C9A C8A 119.8(3) . . ?
C10A C9A H9A 120.1 . . ?
C9A C10A H10A 120.1 . . ?
C9A C10A C11A 119.8(2) . . ?
C11A C10A H10A 120.1 . . ?
C10A C11A H11A 119.2 . . ?
C10A C11A C12A 121.6(3) . . ?
C12A C11A H11A 119.2 . . ?
C7A C12A C13A 121.7(2) . . ?
C11A C12A C7A 117.9(2) . . ?
C11A C12A C13A 120.4(2) . . ?
C12A C13A H13E 108.4 . . ?
C12A C13A H13F 108.4 . . ?
C12A C13A C14A 115.7(2) . . ?
H13E C13A H13F 107.4 . . ?
C14A C13A H13E 108.4 . . ?
C14A C13A H13F 108.4 . . ?
O1A C14A C13A 116.2(2) . . ?
O2A C14A O1A 124.5(2) . . ?
O2A C14A C13A 119.4(2) . . ?
C1B N1B H1B 114(2) . . ?
C1B N1B C7B 123.47(19) . . ?
C7B N1B H1B 114(2) . . ?
N1B C1B C2B 123.3(2) . . ?
N1B C1B C6B 121.5(2) . . ?
C2B C1B C6B 115.0(2) . . ?
C1B C2B Cl1B 120.21(18) . . ?
C3B C2B C1B 122.5(2) . . ?
C3B C2B Cl1B 117.23(19) . . ?
C2B C3B H3B 120.1 . . ?
C4B C3B C2B 119.8(2) . . ?
C4B C3B H3B 120.1 . . ?
C3B C4B H4B 119.9 . . ?
C3B C4B C5B 120.2(2) . . ?
C5B C4B H4B 119.9 . . ?
C4B C5B H5B 120.4 . . ?
C6B C5B C4B 119.3(3) . . ?
C6B C5B H5B 120.4 . . ?
C1B C6B Cl2B 118.46(19) . . ?
C5B C6B C1B 123.1(2) . . ?
C5B C6B Cl2B 118.5(2) . . ?
C8B C7B N1B 121.6(2) . . ?
C8B C7B C12B 119.9(2) . . ?
C12B C7B N1B 118.5(2) . . ?
C7B C8B H8B 119.7 . . ?
C9B C8B C7B 120.7(2) . . ?
C9B C8B H8B 119.7 . . ?
C8B C9B H9B 120.0 . . ?
C8B C9B C10B 120.1(3) . . ?
C10B C9B H9B 120.0 . . ?
C9B C10B H10B 120.3 . . ?
C9B C10B C11B 119.4(2) . . ?
C11B C10B H10B 120.3 . . ?
C10B C11B H11B 119.3 . . ?
C10B C11B C12B 121.4(3) . . ?
C12B C11B H11B 119.3 . . ?
C7B C12B C11B 118.4(2) . . ?
C7B C12B C13B 122.1(2) . . ?
C11B C12B C13B 119.5(2) . . ?
C12B C13B H13G 109.6 . . ?
C12B C13B H13H 109.6 . . ?
C12B C13B C14B 110.43(19) . . ?
H13G C13B H13H 108.1 . . ?
C14B C13B H13G 109.6 . . ?
C14B C13B H13H 109.6 . . ?
O1AB C14B O2AB 125.1(2) . . ?
O1AB C14B C13B 117.8(2) . . ?
O2AB C14B C13B 117.1(2) . . ?
H1PA N1P H1PB 109.5 . . ?
H1PA N1P H1PC 109.5 . . ?
H1PB N1P H1PC 109.5 . . ?
C2P N1P H1PA 109.5 . . ?
C2P N1P H1PB 109.5 . . ?
C2P N1P H1PC 109.5 . . ?
N1P C2P H2PA 109.4 . . ?
N1P C2P H2PB 109.4 . . ?
N1P C2P C3P 111.3(2) . . ?
H2PA C2P H2PB 108.0 . . ?
C3P C2P H2PA 109.4 . . ?
C3P C2P H2PB 109.4 . . ?
C2P C3P H3PA 109.6 . . ?
C2P C3P H3PB 109.6 . . ?
C2P C3P C4P 110.5(2) . . ?
H3PA C3P H3PB 108.1 . . ?
C4P C3P H3PA 109.6 . . ?
C4P C3P H3PB 109.6 . . ?
C3P C4P H4PA 109.2 . . ?
C3P C4P H4PB 109.2 . . ?
H4PA C4P H4PB 107.9 . . ?
N5P C4P C3P 111.9(2) . . ?
N5P C4P H4PA 109.2 . . ?
N5P C4P H4PB 109.2 . . ?
C4P N5P H5PA 109.5 . . ?
C4P N5P H5PB 109.5 . . ?
C4P N5P H5PC 109.5 . . ?
H5PA N5P H5PB 109.5 . . ?
H5PA N5P H5PC 109.5 . . ?
H5PB N5P H5PC 109.5 . . ?
H1NA N1N H1NB 109.5 . . ?
H1NA N1N H1NC 109.5 . . ?
H1NB N1N H1NC 109.5 . . ?
C2N N1N H1NA 109.5 . . ?
C2N N1N H1NB 109.5 . . ?
C2N N1N H1NC 109.5 . . ?
N1N C2N H2NA 109.0 . . ?
N1N C2N H2NB 109.0 . . ?
N1N C2N C3N 113.1(2) . . ?
H2NA C2N H2NB 107.8 . . ?
C3N C2N H2NA 109.0 . . ?
C3N C2N H2NB 109.0 . . ?
C2N C3N H3NA 108.9 . . ?
C2N C3N H3NB 108.9 . . ?
H3NA C3N H3NB 107.7 . . ?
C4N C3N C2N 113.6(2) . . ?
C4N C3N H3NA 108.9 . . ?
C4N C3N H3NB 108.9 . . ?
C3N C4N H4NA 109.4 . . ?
C3N C4N H4NB 109.4 . . ?
H4NA C4N H4NB 108.0 . . ?
N5N C4N C3N 111.0(2) . . ?
N5N C4N H4NA 109.4 . . ?
N5N C4N H4NB 109.4 . . ?
C4N N5N H5NA 109.5 . . ?
C4N N5N H5NB 109.5 . . ?
C4N N5N H5NC 109.5 . . ?
H5NA N5N H5NB 109.5 . . ?
H5NA N5N H5NC 109.5 . . ?
H5NB N5N H5NC 109.5 . . ?
H6WA O6W H6WB 104.3 . . ?
H3WA O3W H3WB 104.5 . . ?
H5WA O5W H5WB 104.5 . . ?
H8WA O8WA H8WB 104.5 . . ?
H4WA O4W H4WB 104.469(1) . . ?
H1WA O1W H1WB 104.5 . . ?
H7WA O7W H7WB 104.6 . . ?
H2WA O2W H2WB 104.3 . . ?
H8WC O8WB H8WD 104.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
N1C H1C O2C 0.85(2) 2.11(2) 2.860(3) 146(2) . yes
N1P H1PB O1AB 0.89 1.88 2.759(3) 169.3 . yes
N1P H1PC O1D 0.89 1.87 2.758(3) 172.0 . yes
N5P H5PA O1C 0.89 1.87 2.749(3) 169.8 1_554 yes
N5P H5PB O1D 0.89 1.99 2.870(3) 172.7 1_455 yes
N5P H5PC O6W 0.89 1.98 2.848(3) 166.6 . yes
N1N H1NB O1A 0.89 1.96 2.837(3) 170.0 1_655 yes
N5N H5NA O1AB 0.89 1.97 2.810(3) 156.0 . yes
N5N H5NB O2D 0.89 1.90 2.784(3) 173.1 . yes
N5N H5NC O3W 0.89 2.04 2.868(3) 153.6 1_556 yes
O6W H6WA O7W 0.85 1.87 2.695(4) 161.3 . yes
O6W H6WB O2AB 0.85 2.01 2.850(3) 171.6 1_455 yes
O3W H3WA O2C 0.85 1.87 2.717(3) 172.5 1_554 yes
O3W H3WB O1A 0.85 2.00 2.795(3) 155.9 1_554 yes
O1W H1WA O2A 0.85 1.87 2.715(3) 169.5 . yes
O7W H7WA O1A 0.85 1.92 2.738(3) 161.1 1_554 yes
O2W H2WA O1W 0.85 1.95 2.781(4) 164.9 . yes
O2W H2WB O2C 0.85 2.02 2.844(3) 163.9 . yes
O8WB H8WD O5W 0.85 2.02 2.853(11) 166.9 . yes

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
Cl1C C2C C3C C4C 175.7(2) . . . . ?
N1C C1C C2C Cl1C 3.1(3) . . . . ?
N1C C1C C2C C3C -178.4(2) . . . . ?
N1C C1C C6C Cl2C -1.1(3) . . . . ?
N1C C1C C6C C5C 179.7(2) . . . . ?
N1C C7C C8C C9C -178.3(2) . . . . ?
N1C C7C C12C C11C 178.4(2) . . . . ?
N1C C7C C12C C13C -2.1(3) . . . . ?
C1C N1C C7C C8C 16.3(3) . . . . ?
C1C N1C C7C C12C -164.5(2) . . . . ?
C1C C2C C3C C4C -2.9(4) . . . . ?
C2C C1C C6C Cl2C 174.59(16) . . . . ?
C2C C1C C6C C5C -4.5(3) . . . . ?
C2C C3C C4C C5C -1.8(4) . . . . ?
C3C C4C C5C C6C 3.1(4) . . . . ?
C4C C5C C6C C1C 0.2(4) . . . . ?
C4C C5C C6C Cl2C -178.9(2) . . . . ?
C6C C1C C2C Cl1C -172.63(17) . . . . ?
C6C C1C C2C C3C 5.9(3) . . . . ?
C7C N1C C1C C2C 52.7(3) . . . . ?
C7C N1C C1C C6C -131.9(2) . . . . ?
C7C C8C C9C C10C -0.7(4) . . . . ?
C7C C12C C13C C14C -79.2(3) . . . . ?
C8C C7C C12C C11C -2.4(3) . . . . ?
C8C C7C C12C C13C 177.1(2) . . . . ?
C8C C9C C10C C11C -1.1(4) . . . . ?
C9C C10C C11C C12C 1.1(4) . . . . ?
C10C C11C C12C C7C 0.6(4) . . . . ?
C10C C11C C12C C13C -178.9(2) . . . . ?
C11C C12C C13C C14C 100.3(3) . . . . ?
C12C C7C C8C C9C 2.5(3) . . . . ?
C12C C13C C14C O1C -112.0(3) . . . . ?
C12C C13C C14C O2C 66.2(3) . . . . ?
N1D C1D C2D Cl1D 0.5(3) . . . . ?
N1D C1D C2D C3D -178.8(2) . . . . ?
N1D C1D C6D Cl2D -3.7(3) . . . . ?
N1D C1D C6D C5D 177.6(2) . . . . ?
N1D C7D C8D C9D 177.9(2) . . . . ?
N1D C7D C12D C11D -178.0(2) . . . . ?
N1D C7D C12D C13D -1.8(3) . . . . ?
Cl1D C2D C3D C4D -176.7(2) . . . . ?
C1D N1D C7D C8D -19.6(4) . . . . ?
C1D N1D C7D C12D 159.8(2) . . . . ?
C1D C2D C3D C4D 2.6(4) . . . . ?
C2D C1D C6D Cl2D -178.36(17) . . . . ?
C2D C1D C6D C5D 2.9(3) . . . . ?
C2D C3D C4D C5D 0.6(4) . . . . ?
C3D C4D C5D C6D -1.9(4) . . . . ?
C4D C5D C6D C1D 0.0(4) . . . . ?
C4D C5D C6D Cl2D -178.7(2) . . . . ?
C6D C1D C2D Cl1D 175.02(17) . . . . ?
C6D C1D C2D C3D -4.2(3) . . . . ?
C7D N1D C1D C2D -52.4(3) . . . . ?
C7D N1D C1D C6D 133.4(2) . . . . ?
C7D C8D C9D C10D 0.2(4) . . . . ?
C7D C12D C13D C14D 68.1(3) . . . . ?
C8D C7D C12D C11D 1.5(3) . . . . ?
C8D C7D C12D C13D 177.7(2) . . . . ?
C8D C9D C10D C11D 1.1(4) . . . . ?
C9D C10D C11D C12D -1.2(4) . . . . ?
C10D C11D C12D C7D -0.1(4) . . . . ?
C10D C11D C12D C13D -176.4(2) . . . . ?
C11D C12D C13D C14D -115.8(2) . . . . ?
C12D C7D C8D C9D -1.5(4) . . . . ?
C12D C13D C14D O1D -8.3(3) . . . . ?
C12D C13D C14D O2D 174.6(2) . . . . ?
Cl1A C2A C3A C4A -179.5(2) . . . . ?
C1A N1A C7A C8A 19.2(4) . . . . ?
C1A N1A C7A C12A -161.6(2) . . . . ?
C1A C2A C3A C4A 0.0(4) . . . . ?
N1A C1A C2A Cl1A 0.6(3) . . . . ?
N1A C1A C2A C3A -178.9(2) . . . . ?
N1A C1A C6A Cl2A 2.0(3) . . . . ?
N1A C1A C6A C5A -179.8(2) . . . . ?
N1A C7A C8A C9A -178.9(2) . . . . ?
N1A C7A C12A C11A 179.5(2) . . . . ?
N1A C7A C12A C13A 1.4(3) . . . . ?
C2A C1A N1A C7A -133.3(2) . . . . ?
C2A C1A C6A Cl2A -173.49(17) . . . . ?
C2A C1A C6A C5A 4.7(3) . . . . ?
C2A C3A C4A C5A 2.2(4) . . . . ?
C3A C4A C5A C6A -0.9(4) . . . . ?
C4A C5A C6A C1A -2.8(4) . . . . ?
C4A C5A C6A Cl2A 175.5(2) . . . . ?
C6A C1A N1A C7A 51.4(3) . . . . ?
C6A C1A C2A Cl1A 176.19(17) . . . . ?
C6A C1A C2A C3A -3.3(3) . . . . ?
C7A C8A C9A C10A -1.4(4) . . . . ?
C7A C12A C13A C14A -67.9(3) . . . . ?
C8A C7A C12A C11A -1.3(3) . . . . ?
C8A C7A C12A C13A -179.4(2) . . . . ?
C8A C9A C10A C11A 0.5(4) . . . . ?
C9A C10A C11A C12A 0.1(4) . . . . ?
C10A C11A C12A C7A 0.3(4) . . . . ?
C10A C11A C12A C13A 178.4(2) . . . . ?
C11A C12A C13A C14A 114.0(3) . . . . ?
C12A C7A C8A C9A 1.9(4) . . . . ?
C12A C13A C14A O1A -171.2(2) . . . . ?
C12A C13A C14A O2A 8.8(4) . . . . ?
N1B C1B C2B Cl1B -3.0(3) . . . . ?
N1B C1B C2B C3B 179.1(2) . . . . ?
N1B C1B C6B Cl2B 1.2(3) . . . . ?
N1B C1B C6B C5B 179.9(2) . . . . ?
N1B C7B C8B C9B 177.8(2) . . . . ?
N1B C7B C12B C11B -178.6(2) . . . . ?
N1B C7B C12B C13B 1.9(3) . . . . ?
C1B N1B C7B C8B -15.9(4) . . . . ?
C1B N1B C7B C12B 164.3(2) . . . . ?
C1B C2B C3B C4B 2.2(4) . . . . ?
Cl1B C2B C3B C4B -175.8(2) . . . . ?
C2B C1B C6B Cl2B -175.30(16) . . . . ?
C2B C1B C6B C5B 3.3(3) . . . . ?
C2B C3B C4B C5B 1.6(4) . . . . ?
C3B C4B C5B C6B -2.7(4) . . . . ?
C4B C5B C6B C1B 0.1(4) . . . . ?
C4B C5B C6B Cl2B 178.7(2) . . . . ?
C6B C1B C2B Cl1B 173.50(16) . . . . ?
C6B C1B C2B C3B -4.5(3) . . . . ?
C7B N1B C1B C2B -53.0(3) . . . . ?
C7B N1B C1B C6B 130.8(2) . . . . ?
C7B C8B C9B C10B 1.4(4) . . . . ?
C7B C12B C13B C14B 79.3(3) . . . . ?
C8B C7B C12B C11B 1.6(3) . . . . ?
C8B C7B C12B C13B -177.8(2) . . . . ?
C8B C9B C10B C11B 0.4(4) . . . . ?
C9B C10B C11B C12B -1.2(4) . . . . ?
C10B C11B C12B C7B 0.2(4) . . . . ?
C10B C11B C12B C13B 179.7(2) . . . . ?
C11B C12B C13B C14B -100.1(3) . . . . ?
C12B C7B C8B C9B -2.5(4) . . . . ?
C12B C13B C14B O1AB 105.7(3) . . . . ?
C12B C13B C14B O2AB -74.4(3) . . . . ?
N1P C2P C3P C4P -177.5(2) . . . . ?
C2P C3P C4P N5P -174.6(2) . . . . ?
N1N C2N C3N C4N -71.6(3) . . . . ?
C2N C3N C4N N5N 172.0(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;

# start Validation Reply Form
_vrf_PLAT420_exp_396_criproh_auto 
;
PROBLEM: D-H Bond Without Acceptor O4W--H4WB . Please Check
RESPONSE: True. See refine special details for explanation.

PROBLEM: D-H Bond Without Acceptor O7W--H7WB . Please Check
RESPONSE: True. H atom points into hydrophobic space over a 
phenyl ring (at 2.55 Ang from plane).
;
# end Validation Reply Form
