# Electronic Supplementary Material (ESI) for Chemical Science.
# This journal is © The Royal Society of Chemistry 2014

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#                                CCDC 
# 
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# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
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#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
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#  except for the purpose of generating routine backup copies
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#  data retrieval see:
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#  from this site to visualise CIF-encoded structures and 
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data_mo_20130724a_0m

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C20 H19 Cl N2 O4'
_chemical_formula_sum            'C20 H19 Cl N2 O4'
_chemical_formula_weight         386.82
_chemical_absolute_configuration unknown

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'P 21'
_symmetry_space_group_name_Hall  'P 2yb'

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

_cell_length_a                   11.1925(12)
_cell_length_b                   8.1206(9)
_cell_length_c                   21.465(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.402(3)
_cell_angle_gamma                90.00
_cell_volume                     1912.5(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    5975
_cell_measurement_theta_min      2.40
_cell_measurement_theta_max      27.83

_exptl_crystal_description       Prism
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.36
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.25
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.343
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             808
_exptl_absorpt_coefficient_mu    0.228
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9225
_exptl_absorpt_correction_T_max  0.9453
_exptl_absorpt_process_details   'SADABS (Bruker, 2002)'

_diffrn_ambient_temperature      298(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX II area-detector diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11292
_diffrn_reflns_av_R_equivalents  0.0233
_diffrn_reflns_av_sigmaI/netI    0.0355
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         1.86
_diffrn_reflns_theta_max         25.50
_reflns_number_total             5728
_reflns_number_gt                5132
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'SMART (Bruker, 2002)'
_computing_cell_refinement       'SAINT (Bruker, 2002)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'XP (Bruker, 2002)'
_computing_publication_material  'SHELXL-97 (Bruker, 2002)'

_refine_special_details          
;
 Refinement of F² against ALL reflections.  The weighted R-factor wR and
 goodness of fit S are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The threshold expression of
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is
 not relevant to the choice of reflections for refinement.  R-factors based
 on F² are statistically about twice as large as those based on F, and R-
 factors based on ALL data will be even larger.
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0812P)²+0.1052P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.01(7)
_refine_ls_number_reflns         5728
_refine_ls_number_parameters     491
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0440
_refine_ls_R_factor_gt           0.0381
_refine_ls_wR_factor_ref         0.1229
_refine_ls_wR_factor_gt          0.1157
_refine_ls_goodness_of_fit_ref   1.085
_refine_ls_restrained_S_all      1.085
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl -0.01424(6) 0.12053(17) 0.12324(5) 0.0850(3) Uani 1 1 d . . .
Cl2 Cl 0.74970(8) 0.62795(15) 0.46864(5) 0.0908(4) Uani 1 1 d . . .
O1 O 0.28445(16) 0.3971(2) 0.04352(11) 0.0561(5) Uani 1 1 d . . .
O2 O 0.43091(17) 0.2705(3) 0.00556(10) 0.0587(5) Uani 1 1 d . . .
O3 O 0.11303(15) 0.1412(3) -0.00094(9) 0.0521(4) Uani 1 1 d . . .
O4 O 0.2001(2) -0.1020(3) 0.00035(12) 0.0719(7) Uani 1 1 d . . .
O5 O 0.98604(16) 0.9050(3) 0.36081(10) 0.0609(6) Uani 1 1 d . . .
O6 O 0.9761(2) 1.1741(4) 0.34028(13) 0.0843(8) Uani 1 1 d . . .
O7 O 0.9250(2) 0.9705(4) 0.47888(9) 0.0741(7) Uani 1 1 d . . .
O8 O 0.7826(3) 1.1544(6) 0.47820(15) 0.1160(14) Uani 1 1 d . . .
N1 N 0.52935(19) 0.3680(3) 0.22771(11) 0.0516(5) Uani 1 1 d . . .
H1A H 0.6010 0.4109 0.2352 0.062 Uiso 1 1 calc R . .
N2 N 0.41407(18) -0.0027(3) 0.07460(10) 0.0429(5) Uani 1 1 d . . .
H2A H 0.4553 0.0109 0.0435 0.064 Uiso 1 1 d R . .
H2B H 0.3867 -0.1057 0.0740 0.064 Uiso 1 1 d R . .
N3 N 0.6391(2) 0.8821(4) 0.18401(12) 0.0665(7) Uani 1 1 d . . .
H3A H 0.6011 0.9239 0.1488 0.080 Uiso 1 1 calc R . .
N4 N 0.7377(2) 1.1891(3) 0.34966(15) 0.0652(7) Uani 1 1 d . . .
H4A H 0.7873 1.2661 0.3397 0.098 Uiso 1 1 d R . .
H4B H 0.6963 1.2298 0.3775 0.098 Uiso 1 1 d R . .
C1 C 0.4493(2) 0.3716(4) 0.26794(13) 0.0484(6) Uani 1 1 d . . .
C2 C 0.4611(3) 0.4416(5) 0.32829(15) 0.0694(9) Uani 1 1 d . . .
H2 H 0.5324 0.4941 0.3480 0.083 Uiso 1 1 calc R . .
C3 C 0.3619(4) 0.4290(5) 0.35723(16) 0.0810(11) Uani 1 1 d . . .
H3 H 0.3665 0.4747 0.3974 0.097 Uiso 1 1 calc R . .
C4 C 0.2557(4) 0.3502(5) 0.32815(17) 0.0768(10) Uani 1 1 d . . .
H4 H 0.1906 0.3441 0.3491 0.092 Uiso 1 1 calc R . .
C5 C 0.2446(3) 0.2812(4) 0.26916(14) 0.0566(7) Uani 1 1 d . . .
H5 H 0.1726 0.2290 0.2501 0.068 Uiso 1 1 calc R . .
C6 C 0.3425(2) 0.2899(3) 0.23779(12) 0.0431(5) Uani 1 1 d . . .
C7 C 0.3637(2) 0.2342(3) 0.17728(11) 0.0382(5) Uani 1 1 d . . .
C8 C 0.4773(2) 0.2847(4) 0.17315(12) 0.0444(5) Uani 1 1 d . . .
H8 H 0.5144 0.2660 0.1387 0.053 Uiso 1 1 calc R . .
C9 C 0.26741(18) 0.1496(3) 0.12859(11) 0.0351(5) Uani 1 1 d . . .
H9 H 0.1993 0.2270 0.1179 0.042 Uiso 1 1 calc R . .
C10 C 0.2176(2) -0.0036(3) 0.15570(11) 0.0399(5) Uani 1 1 d . . .
C11 C 0.2956(3) -0.1244(4) 0.18507(15) 0.0584(7) Uani 1 1 d . . .
H11 H 0.3791 -0.1098 0.1887 0.070 Uiso 1 1 calc R . .
C12 C 0.2539(4) -0.2670(5) 0.20948(18) 0.0809(11) Uani 1 1 d . . .
H12 H 0.3083 -0.3465 0.2292 0.097 Uiso 1 1 calc R . .
C13 C 0.1283(4) -0.2882(6) 0.20376(19) 0.0883(13) Uani 1 1 d . . .
H13 H 0.0984 -0.3858 0.2174 0.106 Uiso 1 1 calc R . .
C14 C 0.0504(4) -0.1685(6) 0.17862(18) 0.0773(11) Uani 1 1 d . . .
H14 H -0.0325 -0.1800 0.1779 0.093 Uiso 1 1 calc R . .
C15 C 0.0937(2) -0.0282(4) 0.15389(13) 0.0551(7) Uani 1 1 d . . .
C16 C 0.31102(18) 0.1108(3) 0.06520(10) 0.0337(4) Uani 1 1 d . . .
C17 C 0.3498(2) 0.2673(3) 0.03486(11) 0.0397(5) Uani 1 1 d . . .
C18 C 0.3170(4) 0.5494(5) 0.0167(3) 0.1004(16) Uani 1 1 d . . .
H18A H 0.4009 0.5745 0.0340 0.151 Uiso 1 1 calc R . .
H18B H 0.2662 0.6365 0.0269 0.151 Uiso 1 1 calc R . .
H18C H 0.3057 0.5387 -0.0286 0.151 Uiso 1 1 calc R . .
C19 C 0.2015(2) 0.0361(3) 0.01748(11) 0.0369(5) Uani 1 1 d . . .
C20 C 0.0041(2) 0.0756(5) -0.04162(17) 0.0668(9) Uani 1 1 d . . .
H20A H 0.0256 0.0250 -0.0783 0.100 Uiso 1 1 calc R . .
H20B H -0.0526 0.1634 -0.0549 0.100 Uiso 1 1 calc R . .
H20C H -0.0325 -0.0050 -0.0186 0.100 Uiso 1 1 calc R . .
C21 C 0.75127(19) 0.7141(4) 0.25544(11) 0.0418(6) Uani 1 1 d . . .
C22 C 0.8218(2) 0.5751(4) 0.27419(13) 0.0495(6) Uani 1 1 d . . .
H22 H 0.8574 0.5596 0.3167 0.059 Uiso 1 1 calc R . .
C23 C 0.8384(3) 0.4605(5) 0.22933(15) 0.0631(8) Uani 1 1 d . . .
H23 H 0.8865 0.3682 0.2417 0.076 Uiso 1 1 calc R . .
C24 C 0.7837(3) 0.4815(5) 0.16526(15) 0.0677(9) Uani 1 1 d . . .
H24 H 0.7943 0.4013 0.1359 0.081 Uiso 1 1 calc R . .
C25 C 0.7151(3) 0.6171(5) 0.14504(13) 0.0632(8) Uani 1 1 d . . .
H25 H 0.6794 0.6309 0.1024 0.076 Uiso 1 1 calc R . .
C26 C 0.7001(2) 0.7346(4) 0.19032(12) 0.0518(7) Uani 1 1 d . . .
C27 C 0.6483(3) 0.9514(5) 0.24228(14) 0.0589(7) Uani 1 1 d . . .
H27 H 0.6130 1.0511 0.2500 0.071 Uiso 1 1 calc R . .
C28 C 0.7162(2) 0.8550(4) 0.28787(12) 0.0437(6) Uani 1 1 d . . .
C29 C 0.74390(19) 0.8798(3) 0.35911(11) 0.0412(5) Uani 1 1 d . . .
H29 H 0.8009 0.7927 0.3773 0.049 Uiso 1 1 calc R . .
C30 C 0.6314(2) 0.8631(4) 0.38910(12) 0.0437(5) Uani 1 1 d . . .
C31 C 0.5279(2) 0.9571(5) 0.36771(16) 0.0619(8) Uani 1 1 d . . .
H31 H 0.5263 1.0292 0.3339 0.074 Uiso 1 1 calc R . .
C32 C 0.4260(3) 0.9454(5) 0.39600(19) 0.0736(10) Uani 1 1 d . . .
H32 H 0.3580 1.0105 0.3812 0.088 Uiso 1 1 calc R . .
C33 C 0.4256(3) 0.8406(5) 0.44456(19) 0.0700(9) Uani 1 1 d . . .
H33 H 0.3572 0.8328 0.4629 0.084 Uiso 1 1 calc R . .
C34 C 0.5254(3) 0.7462(4) 0.46673(15) 0.0609(8) Uani 1 1 d . . .
H34 H 0.5256 0.6742 0.5004 0.073 Uiso 1 1 calc R . .
C35 C 0.6269(2) 0.7578(4) 0.43884(12) 0.0481(6) Uani 1 1 d . . .
C36 C 0.8095(2) 1.0485(4) 0.37784(13) 0.0467(6) Uani 1 1 d . . .
C37 C 0.9330(2) 1.0508(4) 0.35686(12) 0.0499(7) Uani 1 1 d . . .
C38 C 1.1109(3) 0.9020(8) 0.3529(2) 0.0905(14) Uani 1 1 d . . .
H38A H 1.1178 0.9616 0.3151 0.136 Uiso 1 1 calc R . .
H38B H 1.1361 0.7901 0.3492 0.136 Uiso 1 1 calc R . .
H38C H 1.1619 0.9525 0.3891 0.136 Uiso 1 1 calc R . .
C39 C 0.8368(2) 1.0662(4) 0.45080(14) 0.0531(7) Uani 1 1 d . . .
C40 C 0.9528(5) 0.9787(9) 0.54817(16) 0.1036(16) Uani 1 1 d . . .
H40A H 0.9808 1.0874 0.5613 0.155 Uiso 1 1 calc R . .
H40B H 1.0152 0.9000 0.5644 0.155 Uiso 1 1 calc R . .
H40C H 0.8807 0.9542 0.5643 0.155 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
Cl1 C15 1.743(4) . ?
Cl2 C35 1.750(3) . ?
O1 C17 1.316(3) . ?
O1 C18 1.441(4) . ?
O2 C17 1.203(3) . ?
O3 C19 1.308(3) . ?
O3 C20 1.453(3) . ?
O4 C19 1.179(3) . ?
O5 C37 1.320(4) . ?
O5 C38 1.441(3) . ?
O6 C37 1.197(4) . ?
O7 C39 1.307(4) . ?
O7 C40 1.459(4) . ?
O8 C39 1.169(4) . ?
N1 C1 1.362(4) . ?
N1 C8 1.378(3) . ?
N1 H1A 0.8600 . ?
N2 C16 1.459(3) . ?
N2 H2A 0.8900 . ?
N2 H2B 0.8900 . ?
N3 C27 1.357(4) . ?
N3 C26 1.373(5) . ?
N3 H3A 0.8600 . ?
N4 C36 1.457(4) . ?
N4 H4A 0.8900 . ?
N4 H4B 0.8900 . ?
C1 C2 1.397(4) . ?
C1 C6 1.408(4) . ?
C2 C3 1.379(5) . ?
C2 H2 0.9300 . ?
C3 C4 1.386(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.368(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.396(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.439(4) . ?
C7 C8 1.355(3) . ?
C7 C9 1.510(3) . ?
C8 H8 0.9300 . ?
C9 C10 1.525(3) . ?
C9 C16 1.566(3) . ?
C9 H9 0.9800 . ?
C10 C11 1.380(4) . ?
C10 C15 1.394(3) . ?
C11 C12 1.390(5) . ?
C11 H11 0.9300 . ?
C12 C13 1.397(6) . ?
C12 H12 0.9300 . ?
C13 C14 1.346(6) . ?
C13 H13 0.9300 . ?
C14 C15 1.384(5) . ?
C14 H14 0.9300 . ?
C16 C17 1.530(3) . ?
C16 C19 1.556(3) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 C22 1.390(4) . ?
C21 C26 1.412(4) . ?
C21 C28 1.434(4) . ?
C22 C23 1.379(5) . ?
C22 H22 0.9300 . ?
C23 C24 1.401(5) . ?
C23 H23 0.9300 . ?
C24 C25 1.363(5) . ?
C24 H24 0.9300 . ?
C25 C26 1.395(5) . ?
C25 H25 0.9300 . ?
C27 C28 1.361(4) . ?
C27 H27 0.9300 . ?
C28 C29 1.513(4) . ?
C29 C30 1.529(3) . ?
C29 C36 1.569(4) . ?
C29 H29 0.9800 . ?
C30 C35 1.377(4) . ?
C30 C31 1.388(4) . ?
C31 C32 1.397(4) . ?
C31 H31 0.9300 . ?
C32 C33 1.346(5) . ?
C32 H32 0.9300 . ?
C33 C34 1.361(5) . ?
C33 H33 0.9300 . ?
C34 C35 1.388(4) . ?
C34 H34 0.9300 . ?
C36 C37 1.535(3) . ?
C36 C39 1.542(4) . ?
C38 H38A 0.9600 . ?
C38 H38B 0.9600 . ?
C38 H38C 0.9600 . ?
C40 H40A 0.9600 . ?
C40 H40B 0.9600 . ?
C40 H40C 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
C17 O1 C18 116.1(2) . . ?
C19 O3 C20 115.9(2) . . ?
C37 O5 C38 116.2(3) . . ?
C39 O7 C40 115.6(3) . . ?
C1 N1 C8 109.2(2) . . ?
C1 N1 H1A 125.4 . . ?
C8 N1 H1A 125.4 . . ?
C16 N2 H2A 109.3 . . ?
C16 N2 H2B 109.4 . . ?
H2A N2 H2B 109.5 . . ?
C27 N3 C26 109.0(2) . . ?
C27 N3 H3A 125.5 . . ?
C26 N3 H3A 125.5 . . ?
C36 N4 H4A 109.3 . . ?
C36 N4 H4B 109.3 . . ?
H4A N4 H4B 109.5 . . ?
N1 C1 C2 130.0(3) . . ?
N1 C1 C6 107.7(2) . . ?
C2 C1 C6 122.3(3) . . ?
C3 C2 C1 116.8(3) . . ?
C3 C2 H2 121.6 . . ?
C1 C2 H2 121.6 . . ?
C2 C3 C4 121.8(3) . . ?
C2 C3 H3 119.1 . . ?
C4 C3 H3 119.1 . . ?
C5 C4 C3 121.2(3) . . ?
C5 C4 H4 119.4 . . ?
C3 C4 H4 119.4 . . ?
C4 C5 C6 119.3(3) . . ?
C4 C5 H5 120.3 . . ?
C6 C5 H5 120.3 . . ?
C5 C6 C1 118.6(2) . . ?
C5 C6 C7 134.8(2) . . ?
C1 C6 C7 106.6(2) . . ?
C8 C7 C6 106.7(2) . . ?
C8 C7 C9 130.0(2) . . ?
C6 C7 C9 123.1(2) . . ?
C7 C8 N1 109.7(2) . . ?
C7 C8 H8 125.1 . . ?
N1 C8 H8 125.1 . . ?
C7 C9 C10 111.82(19) . . ?
C7 C9 C16 113.01(17) . . ?
C10 C9 C16 111.56(19) . . ?
C7 C9 H9 106.7 . . ?
C10 C9 H9 106.7 . . ?
C16 C9 H9 106.7 . . ?
C11 C10 C15 116.6(3) . . ?
C11 C10 C9 120.5(2) . . ?
C15 C10 C9 122.9(2) . . ?
C10 C11 C12 122.4(3) . . ?
C10 C11 H11 118.8 . . ?
C12 C11 H11 118.8 . . ?
C11 C12 C13 118.5(4) . . ?
C11 C12 H12 120.8 . . ?
C13 C12 H12 120.8 . . ?
C14 C13 C12 120.5(3) . . ?
C14 C13 H13 119.8 . . ?
C12 C13 H13 119.8 . . ?
C13 C14 C15 120.0(3) . . ?
C13 C14 H14 120.0 . . ?
C15 C14 H14 120.0 . . ?
C14 C15 C10 121.9(3) . . ?
C14 C15 Cl1 116.5(3) . . ?
C10 C15 Cl1 121.5(2) . . ?
N2 C16 C17 107.52(17) . . ?
N2 C16 C19 110.07(19) . . ?
C17 C16 C19 107.23(18) . . ?
N2 C16 C9 112.38(17) . . ?
C17 C16 C9 111.44(19) . . ?
C19 C16 C9 108.07(17) . . ?
O2 C17 O1 123.7(2) . . ?
O2 C17 C16 123.2(2) . . ?
O1 C17 C16 113.15(18) . . ?
O1 C18 H18A 109.5 . . ?
O1 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O1 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
O4 C19 O3 124.3(2) . . ?
O4 C19 C16 122.4(2) . . ?
O3 C19 C16 113.3(2) . . ?
O3 C20 H20A 109.5 . . ?
O3 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
O3 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C22 C21 C26 118.6(3) . . ?
C22 C21 C28 134.5(2) . . ?
C26 C21 C28 106.9(2) . . ?
C23 C22 C21 119.6(3) . . ?
C23 C22 H22 120.2 . . ?
C21 C22 H22 120.2 . . ?
C22 C23 C24 120.6(3) . . ?
C22 C23 H23 119.7 . . ?
C24 C23 H23 119.7 . . ?
C25 C24 C23 121.4(3) . . ?
C25 C24 H24 119.3 . . ?
C23 C24 H24 119.3 . . ?
C24 C25 C26 117.9(3) . . ?
C24 C25 H25 121.1 . . ?
C26 C25 H25 121.1 . . ?
N3 C26 C25 130.8(3) . . ?
N3 C26 C21 107.3(3) . . ?
C25 C26 C21 121.9(3) . . ?
N3 C27 C28 110.8(3) . . ?
N3 C27 H27 124.6 . . ?
C28 C27 H27 124.6 . . ?
C27 C28 C21 106.1(2) . . ?
C27 C28 C29 128.6(3) . . ?
C21 C28 C29 125.2(2) . . ?
C28 C29 C30 113.12(18) . . ?
C28 C29 C36 111.5(2) . . ?
C30 C29 C36 110.6(2) . . ?
C28 C29 H29 107.1 . . ?
C30 C29 H29 107.1 . . ?
C36 C29 H29 107.1 . . ?
C35 C30 C31 116.2(2) . . ?
C35 C30 C29 122.8(2) . . ?
C31 C30 C29 121.0(2) . . ?
C30 C31 C32 121.2(3) . . ?
C30 C31 H31 119.4 . . ?
C32 C31 H31 119.4 . . ?
C33 C32 C31 120.5(3) . . ?
C33 C32 H32 119.7 . . ?
C31 C32 H32 119.7 . . ?
C32 C33 C34 119.9(3) . . ?
C32 C33 H33 120.1 . . ?
C34 C33 H33 120.1 . . ?
C33 C34 C35 119.8(3) . . ?
C33 C34 H34 120.1 . . ?
C35 C34 H34 120.1 . . ?
C30 C35 C34 122.4(3) . . ?
C30 C35 Cl2 120.71(19) . . ?
C34 C35 Cl2 116.9(2) . . ?
N4 C36 C37 108.9(2) . . ?
N4 C36 C39 109.3(3) . . ?
C37 C36 C39 106.73(19) . . ?
N4 C36 C29 112.69(19) . . ?
C37 C36 C29 109.8(2) . . ?
C39 C36 C29 109.3(2) . . ?
O6 C37 O5 124.5(3) . . ?
O6 C37 C36 122.5(3) . . ?
O5 C37 C36 113.0(2) . . ?
O5 C38 H38A 109.5 . . ?
O5 C38 H38B 109.5 . . ?
H38A C38 H38B 109.5 . . ?
O5 C38 H38C 109.5 . . ?
H38A C38 H38C 109.5 . . ?
H38B C38 H38C 109.5 . . ?
O8 C39 O7 123.5(3) . . ?
O8 C39 C36 123.4(3) . . ?
O7 C39 C36 113.1(2) . . ?
O7 C40 H40A 109.5 . . ?
O7 C40 H40B 109.5 . . ?
H40A C40 H40B 109.5 . . ?
O7 C40 H40C 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 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
C8 N1 C1 C2 -179.9(3) . . . . ?
C8 N1 C1 C6 -0.7(3) . . . . ?
N1 C1 C2 C3 178.3(3) . . . . ?
C6 C1 C2 C3 -0.8(5) . . . . ?
C1 C2 C3 C4 0.3(6) . . . . ?
C2 C3 C4 C5 0.0(7) . . . . ?
C3 C4 C5 C6 0.3(6) . . . . ?
C4 C5 C6 C1 -0.7(5) . . . . ?
C4 C5 C6 C7 -179.7(3) . . . . ?
N1 C1 C6 C5 -178.2(3) . . . . ?
C2 C1 C6 C5 1.0(4) . . . . ?
N1 C1 C6 C7 1.0(3) . . . . ?
C2 C1 C6 C7 -179.8(3) . . . . ?
C5 C6 C7 C8 178.2(3) . . . . ?
C1 C6 C7 C8 -0.8(3) . . . . ?
C5 C6 C7 C9 2.9(5) . . . . ?
C1 C6 C7 C9 -176.1(2) . . . . ?
C6 C7 C8 N1 0.4(3) . . . . ?
C9 C7 C8 N1 175.2(2) . . . . ?
C1 N1 C8 C7 0.2(3) . . . . ?
C8 C7 C9 C10 129.4(3) . . . . ?
C6 C7 C9 C10 -56.5(3) . . . . ?
C8 C7 C9 C16 2.5(4) . . . . ?
C6 C7 C9 C16 176.6(2) . . . . ?
C7 C9 C10 C11 -52.9(3) . . . . ?
C16 C9 C10 C11 74.8(3) . . . . ?
C7 C9 C10 C15 125.5(2) . . . . ?
C16 C9 C10 C15 -106.9(3) . . . . ?
C15 C10 C11 C12 2.6(5) . . . . ?
C9 C10 C11 C12 -178.9(3) . . . . ?
C10 C11 C12 C13 0.2(6) . . . . ?
C11 C12 C13 C14 -3.9(6) . . . . ?
C12 C13 C14 C15 4.8(6) . . . . ?
C13 C14 C15 C10 -1.9(5) . . . . ?
C13 C14 C15 Cl1 -179.3(3) . . . . ?
C11 C10 C15 C14 -1.7(4) . . . . ?
C9 C10 C15 C14 179.8(3) . . . . ?
C11 C10 C15 Cl1 175.5(2) . . . . ?
C9 C10 C15 Cl1 -2.9(4) . . . . ?
C7 C9 C16 N2 62.4(3) . . . . ?
C10 C9 C16 N2 -64.6(2) . . . . ?
C7 C9 C16 C17 -58.3(2) . . . . ?
C10 C9 C16 C17 174.66(18) . . . . ?
C7 C9 C16 C19 -175.91(19) . . . . ?
C10 C9 C16 C19 57.1(2) . . . . ?
C18 O1 C17 O2 -1.4(4) . . . . ?
C18 O1 C17 C16 179.3(3) . . . . ?
N2 C16 C17 O2 22.6(3) . . . . ?
C19 C16 C17 O2 -95.7(3) . . . . ?
C9 C16 C17 O2 146.2(2) . . . . ?
N2 C16 C17 O1 -158.1(2) . . . . ?
C19 C16 C17 O1 83.5(2) . . . . ?
C9 C16 C17 O1 -34.5(3) . . . . ?
C20 O3 C19 O4 4.5(4) . . . . ?
C20 O3 C19 C16 -175.4(2) . . . . ?
N2 C16 C19 O4 10.4(3) . . . . ?
C17 C16 C19 O4 127.1(3) . . . . ?
C9 C16 C19 O4 -112.6(3) . . . . ?
N2 C16 C19 O3 -169.8(2) . . . . ?
C17 C16 C19 O3 -53.1(2) . . . . ?
C9 C16 C19 O3 67.2(2) . . . . ?
C26 C21 C22 C23 -0.9(4) . . . . ?
C28 C21 C22 C23 -179.4(3) . . . . ?
C21 C22 C23 C24 -0.9(4) . . . . ?
C22 C23 C24 C25 1.7(5) . . . . ?
C23 C24 C25 C26 -0.5(5) . . . . ?
C27 N3 C26 C25 178.7(3) . . . . ?
C27 N3 C26 C21 -1.2(3) . . . . ?
C24 C25 C26 N3 178.7(3) . . . . ?
C24 C25 C26 C21 -1.5(4) . . . . ?
C22 C21 C26 N3 -177.9(2) . . . . ?
C28 C21 C26 N3 0.9(3) . . . . ?
C22 C21 C26 C25 2.2(4) . . . . ?
C28 C21 C26 C25 -179.0(2) . . . . ?
C26 N3 C27 C28 1.1(4) . . . . ?
N3 C27 C28 C21 -0.4(3) . . . . ?
N3 C27 C28 C29 -176.4(2) . . . . ?
C22 C21 C28 C27 178.3(3) . . . . ?
C26 C21 C28 C27 -0.3(3) . . . . ?
C22 C21 C28 C29 -5.6(4) . . . . ?
C26 C21 C28 C29 175.8(2) . . . . ?
C27 C28 C29 C30 67.0(4) . . . . ?
C21 C28 C29 C30 -108.2(3) . . . . ?
C27 C28 C29 C36 -58.4(3) . . . . ?
C21 C28 C29 C36 126.3(2) . . . . ?
C28 C29 C30 C35 126.3(3) . . . . ?
C36 C29 C30 C35 -107.8(3) . . . . ?
C28 C29 C30 C31 -54.8(4) . . . . ?
C36 C29 C30 C31 71.2(3) . . . . ?
C35 C30 C31 C32 0.7(5) . . . . ?
C29 C30 C31 C32 -178.3(3) . . . . ?
C30 C31 C32 C33 -0.7(6) . . . . ?
C31 C32 C33 C34 0.6(6) . . . . ?
C32 C33 C34 C35 -0.4(5) . . . . ?
C31 C30 C35 C34 -0.5(4) . . . . ?
C29 C30 C35 C34 178.5(3) . . . . ?
C31 C30 C35 Cl2 178.0(2) . . . . ?
C29 C30 C35 Cl2 -3.0(4) . . . . ?
C33 C34 C35 C30 0.4(5) . . . . ?
C33 C34 C35 Cl2 -178.2(3) . . . . ?
C28 C29 C36 N4 58.9(3) . . . . ?
C30 C29 C36 N4 -67.9(3) . . . . ?
C28 C29 C36 C37 -62.6(3) . . . . ?
C30 C29 C36 C37 170.5(2) . . . . ?
C28 C29 C36 C39 -179.3(2) . . . . ?
C30 C29 C36 C39 53.8(3) . . . . ?
C38 O5 C37 O6 8.9(4) . . . . ?
C38 O5 C37 C36 -169.4(3) . . . . ?
N4 C36 C37 O6 23.7(4) . . . . ?
C39 C36 C37 O6 -94.2(3) . . . . ?
C29 C36 C37 O6 147.5(3) . . . . ?
N4 C36 C37 O5 -158.0(2) . . . . ?
C39 C36 C37 O5 84.1(3) . . . . ?
C29 C36 C37 O5 -34.2(3) . . . . ?
C40 O7 C39 O8 0.3(6) . . . . ?
C40 O7 C39 C36 -178.5(4) . . . . ?
N4 C36 C39 O8 17.7(4) . . . . ?
C37 C36 C39 O8 135.3(4) . . . . ?
C29 C36 C39 O8 -106.1(4) . . . . ?
N4 C36 C39 O7 -163.6(2) . . . . ?
C37 C36 C39 O7 -46.0(3) . . . . ?
C29 C36 C39 O7 72.7(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N2 H2A O2 0.89 2.26 2.695(3) 110.0 .
N2 H2A O2 0.89 2.66 3.247(3) 124.5 2_645
N3 H3A N2 0.86 2.44 3.224(3) 151.7 1_565
N4 H4A O6 0.89 2.24 2.719(4) 113.4 .
N4 H4B O8 0.89 2.27 2.720(4) 111.1 .

_diffrn_measured_fraction_theta_max 0.992
_diffrn_reflns_theta_full        25.50
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.242
_refine_diff_density_min         -0.273
_refine_diff_density_rms         0.060
_database_code_depnum_ccdc_archive 'CCDC 965738'
