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

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  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.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_zhangyuan0608
_audit_creation_date             2014-06-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.05.21 svn.r2940 for OlexSys, GUI svn.r4846)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C21 H19 Cl N2 O5, 0.25(C H2 Cl2)'
_chemical_formula_sum            'C21.25 H19.50 Cl1.50 N2 O5'
_chemical_formula_weight         436.06
_chemical_absolute_configuration ?
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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'

_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           5
_space_group_name_H-M_alt        'C 1 2 1'
_space_group_name_Hall           'C 2y'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'

_cell_length_a                   14.3843(3)
_cell_length_b                   9.8961(3)
_cell_length_c                   28.9183(7)
_cell_angle_alpha                90
_cell_angle_beta                 100.764(2)
_cell_angle_gamma                90
_cell_volume                     4044.06(17)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    4403
_cell_measurement_temperature    292.1(6)
_cell_measurement_theta_max      69.8060
_cell_measurement_theta_min      4.6510
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.601
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68816
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear light yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.432
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1812
_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.21
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0350
_diffrn_reflns_av_unetI/netI     0.0521
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -35
_diffrn_reflns_number            9128
_diffrn_reflns_point_group_measured_fraction_full 0.817
_diffrn_reflns_point_group_measured_fraction_max 0.797
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         70.571
_diffrn_reflns_theta_min         4.670
_diffrn_ambient_temperature      292.1(6)
_diffrn_detector_area_resol_mean 16.0733
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -28.00   17.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   38.0000   30.0000 45

#__ type_ start__ end____ width___ exp.time_
  2 omega  -74.00  -36.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  178.0000   60.0000 38

#__ type_ start__ end____ width___ exp.time_
  3 omega   23.00   72.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000   38.0000   30.0000 49

#__ type_ start__ end____ width___ exp.time_
  4 omega  -61.00  -36.00   1.0000    1.0000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  178.0000 -120.0000 25

#__ type_ start__ end____ width___ exp.time_
  5 omega -110.00  -84.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -      -42.5000  178.0000 -180.0000 26

#__ type_ start__ end____ width___ exp.time_
  6 omega   44.00   79.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       56.0000  -57.0000  150.0000 35

#__ type_ start__ end____ width___ exp.time_
  7 omega   32.00  125.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   57.0000  -60.0000 93

#__ type_ start__ end____ width___ exp.time_
  8 omega  100.00  125.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       56.0000  151.0000   65.0000 25

#__ type_ start__ end____ width___ exp.time_
  9 omega   37.00   63.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   57.0000 -180.0000 26

#__ type_ start__ end____ width___ exp.time_
 10 omega   27.00  122.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   38.0000   90.0000 95

#__ type_ start__ end____ width___ exp.time_
 11 omega   77.00  103.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       56.0000   57.0000 -180.0000 26

#__ type_ start__ end____ width___ exp.time_
 12 omega   23.00  109.00   1.0000    1.5000
omega____ theta____ kappa____ phi______ frames
    -       56.0000 -125.0000  150.0000 86

#__ type_ start__ end____ width___ exp.time_
 13 omega   73.00   99.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -77.0000    0.0000 26

#__ type_ start__ end____ width___ exp.time_
 14 omega   50.00  102.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -111.0000  -30.0000 52

#__ type_ start__ end____ width___ exp.time_
 15 omega   42.00  114.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000 -111.0000 -150.0000 72

#__ type_ start__ end____ width___ exp.time_
 16 omega   60.00   93.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -38.0000  120.0000 33

#__ type_ start__ end____ width___ exp.time_
 17 omega  107.00  133.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   38.0000  -60.0000 26

#__ type_ start__ end____ width___ exp.time_
 18 omega   44.00   94.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -25.0000  -60.0000 50

#__ type_ start__ end____ width___ exp.time_
 19 omega   46.00   86.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -50.0000 -150.0000 40

#__ type_ start__ end____ width___ exp.time_
 20 omega   48.00   87.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -38.0000  -90.0000 39

#__ type_ start__ end____ width___ exp.time_
 21 omega   63.00   91.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -25.0000  -30.0000 28

#__ type_ start__ end____ width___ exp.time_
 22 omega  126.00  177.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  111.0000    0.0000 51

#__ type_ start__ end____ width___ exp.time_
 23 omega   42.00   91.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  -38.0000   90.0000 49

#__ type_ start__ end____ width___ exp.time_
 24 omega   96.00  173.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000   50.0000   90.0000 77

#__ type_ start__ end____ width___ exp.time_
 25 omega   97.00  177.00   1.0000    3.0000
omega____ theta____ kappa____ phi______ frames
    -      112.0000  122.0000  -96.0000 80
;
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0649506000
_diffrn_orient_matrix_UB_12      0.1130793000
_diffrn_orient_matrix_UB_13      -0.0243135000
_diffrn_orient_matrix_UB_21      0.0601454000
_diffrn_orient_matrix_UB_22      0.1058671000
_diffrn_orient_matrix_UB_23      0.0312927000
_diffrn_orient_matrix_UB_31      0.0635953000
_diffrn_orient_matrix_UB_32      0.0152933000
_diffrn_orient_matrix_UB_33      -0.0370440000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'SuperNova (Cu) X-ray Source'
_reflns_Friedel_coverage         0.530
_reflns_Friedel_fraction_full    0.613
_reflns_Friedel_fraction_max     0.588
_reflns_number_gt                5805
_reflns_number_total             6189
_reflns_odcompleteness_completeness 99.87
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET)
(compiled Feb  1 2013,16:14:44)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         0.222
_refine_diff_density_min         -0.308
_refine_diff_density_rms         0.056
_refine_ls_abs_structure_details 
;
 Flack x determined using 1863 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   0.006(12)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     549
_refine_ls_number_reflns         6189
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0513
_refine_ls_R_factor_gt           0.0488
_refine_ls_restrained_S_all      1.038
_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)+(0.0800P)²]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1259
_refine_ls_wR_factor_ref         0.1305
_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) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: H45A(0.5) H45B(0.5)
3.a Secondary CH2 refined with riding coordinates:
 C19(H19A,H19B), C32(H32A,H32B), C41(H41A,H41B), C45(H45A,H45B)
3.b Aromatic/amide H refined with riding coordinates:
 N1(H1), C2(H2), C3(H3), C4(H4), C5(H5), C13(H13), C14(H14), C16(H16),
 C17(H17), N3(H3A), C24(H24), C25(H25), C26(H26), C27(H27), C35(H35), C36(H36),
 C38(H38), C39(H39)
3.c Idealised Me refined as rotating group:
 C18(H18A,H18B,H18C), C22(H22A,H22B,H22C), C40(H40A,H40B,H40C), C44(H44A,H44B,
 H44C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_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 0.56848(10) 0.16678(17) -0.05420(4) 0.0699(4) Uani 1 1 d . . . . .
O1 O 0.66554(17) 0.4804(4) 0.20702(9) 0.0455(7) Uani 1 1 d . . . . .
O2 O 0.7033(3) 0.1946(4) 0.23161(13) 0.0718(11) Uani 1 1 d . . . . .
O3 O 0.6339(2) 0.2198(4) 0.15979(13) 0.0656(10) Uani 1 1 d . . . . .
O4 O 0.9561(2) 0.3273(3) 0.10305(11) 0.0519(7) Uani 1 1 d . . . . .
O5 O 0.9374(2) 0.1241(3) 0.13371(10) 0.0465(7) Uani 1 1 d . . . . .
N1 N 0.7273(2) 0.5469(4) 0.28189(11) 0.0414(7) Uani 1 1 d . . . . .
H1 H 0.6745 0.5550 0.2916 0.050 Uiso 1 1 calc R . . . .
N2 N 0.7046(3) 0.2050(4) 0.18995(13) 0.0493(9) Uani 1 1 d . . . . .
C1 C 0.8154(3) 0.5710(4) 0.30978(13) 0.0357(7) Uani 1 1 d . . . . .
C2 C 0.8355(3) 0.6068(5) 0.35663(14) 0.0469(9) Uani 1 1 d . . . . .
H2 H 0.7873 0.6199 0.3736 0.056 Uiso 1 1 calc R . . . .
C3 C 0.9296(4) 0.6227(5) 0.37775(14) 0.0547(11) Uani 1 1 d . . . . .
H3 H 0.9453 0.6468 0.4093 0.066 Uiso 1 1 calc R . . . .
C4 C 1.0003(3) 0.6028(5) 0.35190(15) 0.0512(10) Uani 1 1 d . . . . .
H4 H 1.0631 0.6138 0.3665 0.061 Uiso 1 1 calc R . . . .
C5 C 0.9799(3) 0.5670(5) 0.30486(15) 0.0435(9) Uani 1 1 d . . . . .
H5 H 1.0285 0.5542 0.2881 0.052 Uiso 1 1 calc R . . . .
C6 C 0.8858(2) 0.5502(4) 0.28283(13) 0.0331(7) Uani 1 1 d . . . . .
C7 C 0.8378(2) 0.5088(4) 0.23511(12) 0.0323(7) Uani 1 1 d . . . . .
C8 C 0.7342(2) 0.5091(4) 0.23759(13) 0.0344(7) Uani 1 1 d . . . . .
C9 C 0.8741(2) 0.4772(4) 0.19693(13) 0.0340(7) Uani 1 1 d . . . . .
C10 C 0.8131(2) 0.4376(4) 0.15029(12) 0.0348(7) Uani 1 1 d . . . . .
H10A H 0.749(3) 0.469(5) 0.1502(14) 0.036(11) Uiso 1 1 d . . . . .
H10B H 0.836(3) 0.496(5) 0.1250(15) 0.034(10) Uiso 1 1 d . . . . .
C11 C 0.8153(2) 0.2863(4) 0.13573(12) 0.0337(7) Uani 1 1 d . . . . .
C12 C 0.7476(2) 0.2586(4) 0.08838(12) 0.0366(7) Uani 1 1 d . . . . .
C13 C 0.7019(3) 0.3610(5) 0.06027(15) 0.0477(9) Uani 1 1 d . . . . .
H13 H 0.7079 0.4497 0.0711 0.057 Uiso 1 1 calc R . . . .
C14 C 0.6474(4) 0.3342(5) 0.01648(16) 0.0556(11) Uani 1 1 d . . . . .
H14 H 0.6176 0.4042 -0.0021 0.067 Uiso 1 1 calc R . . . .
C15 C 0.6380(3) 0.2028(5) 0.00071(14) 0.0480(10) Uani 1 1 d . . . . .
C16 C 0.6820(3) 0.0984(5) 0.02779(15) 0.0495(10) Uani 1 1 d . . . . .
H16 H 0.6754 0.0099 0.0169 0.059 Uiso 1 1 calc R . . . .
C17 C 0.7359(3) 0.1273(5) 0.07138(15) 0.0460(9) Uani 1 1 d . . . . .
H17 H 0.7651 0.0569 0.0899 0.055 Uiso 1 1 calc R . . . .
C18 C 0.9786(3) 0.4862(5) 0.19731(15) 0.0485(10) Uani 1 1 d . . . . .
H18A H 1.0098 0.4094 0.2135 0.073 Uiso 1 1 calc GR . . . .
H18B H 1.0032 0.5675 0.2131 0.073 Uiso 1 1 calc GR . . . .
H18C H 0.9893 0.4875 0.1655 0.073 Uiso 1 1 calc GR . . . .
C19 C 0.7994(3) 0.1904(4) 0.17541(13) 0.0404(8) Uani 1 1 d . . . . .
H19A H 0.8059 0.0981 0.1653 0.048 Uiso 1 1 calc R . . . .
H19B H 0.8487 0.2063 0.2027 0.048 Uiso 1 1 calc R . . . .
C21 C 0.9124(3) 0.2510(4) 0.12290(12) 0.0369(8) Uani 1 1 d . . . . .
C22 C 1.0175(3) 0.0718(6) 0.11543(17) 0.0546(11) Uani 1 1 d . . . . .
H22A H 1.0110 0.0953 0.0828 0.082 Uiso 1 1 calc GR . . . .
H22B H 1.0197 -0.0248 0.1187 0.082 Uiso 1 1 calc GR . . . .
H22C H 1.0749 0.1101 0.1327 0.082 Uiso 1 1 calc GR . . . .
Cl2 Cl 0.60824(9) 0.26246(16) 0.49175(5) 0.0732(4) Uani 1 1 d . . . . .
O6 O 1.06264(17) -0.0672(4) 0.30924(9) 0.0451(7) Uani 1 1 d . . . . .
O7 O 1.0752(2) 0.2249(4) 0.34080(12) 0.0627(9) Uani 1 1 d . . . . .
O8 O 0.9840(3) 0.2198(4) 0.27286(11) 0.0626(9) Uani 1 1 d . . . . .
O9 O 1.0625(2) 0.1023(3) 0.43808(11) 0.0534(8) Uani 1 1 d . . . . .
O10 O 1.0069(2) 0.3134(3) 0.42649(11) 0.0482(7) Uani 1 1 d . . . . .
N3 N 0.9926(2) -0.1314(4) 0.23536(11) 0.0414(7) Uani 1 1 d . . . . .
H3A H 1.0435 -0.1428 0.2242 0.050 Uiso 1 1 calc R . . . .
N4 N 0.9971(2) 0.2245(4) 0.31557(12) 0.0438(7) Uani 1 1 d . . . . .
C23 C 0.9011(3) -0.1507(4) 0.20917(13) 0.0368(8) Uani 1 1 d . . . . .
C24 C 0.8769(3) -0.1877(5) 0.16301(14) 0.0464(9) Uani 1 1 d . . . . .
H24 H 0.9226 -0.2056 0.1450 0.056 Uiso 1 1 calc R . . . .
C25 C 0.7808(3) -0.1976(5) 0.14408(15) 0.0515(10) Uani 1 1 d . . . . .
H25 H 0.7617 -0.2213 0.1126 0.062 Uiso 1 1 calc R . . . .
C26 C 0.7137(3) -0.1731(5) 0.17109(17) 0.0523(10) Uani 1 1 d . . . . .
H26 H 0.6500 -0.1798 0.1576 0.063 Uiso 1 1 calc R . . . .
C27 C 0.7395(3) -0.1381(4) 0.21837(15) 0.0429(8) Uani 1 1 d . . . . .
H27 H 0.6935 -0.1227 0.2365 0.052 Uiso 1 1 calc R . . . .
C28 C 0.8353(2) -0.1266(4) 0.23825(13) 0.0334(7) Uani 1 1 d . . . . .
C29 C 0.8885(2) -0.0863(4) 0.28501(12) 0.0318(7) Uani 1 1 d . . . . .
C30 C 0.9916(2) -0.0926(4) 0.28029(13) 0.0347(7) Uani 1 1 d . . . . .
C31 C 0.8575(2) -0.0520(4) 0.32449(13) 0.0338(7) Uani 1 1 d . . . . .
C32 C 0.9243(2) -0.0083(4) 0.36879(12) 0.0324(7) Uani 1 1 d . . . . .
H32A H 0.9886 -0.0274 0.3651 0.039 Uiso 1 1 calc R . . . .
H32B H 0.9115 -0.0622 0.3949 0.039 Uiso 1 1 calc R . . . .
C33 C 0.9173(2) 0.1435(4) 0.38144(11) 0.0308(7) Uani 1 1 d . . . . .
C34 C 0.8333(2) 0.1736(4) 0.40638(11) 0.0311(7) Uani 1 1 d . . . . .
C35 C 0.7650(3) 0.2705(4) 0.39145(14) 0.0414(8) Uani 1 1 d . . . . .
H35 H 0.7656 0.3176 0.3637 0.050 Uiso 1 1 calc R . . . .
C36 C 0.6948(3) 0.2982(5) 0.41787(17) 0.0493(10) Uani 1 1 d . . . . .
H36 H 0.6489 0.3634 0.4079 0.059 Uiso 1 1 calc R . . . .
C37 C 0.6949(3) 0.2284(5) 0.45823(15) 0.0454(9) Uani 1 1 d . . . . .
C38 C 0.7608(3) 0.1297(5) 0.47379(13) 0.0452(9) Uani 1 1 d . . . . .
H38 H 0.7586 0.0815 0.5012 0.054 Uiso 1 1 calc R . . . .
C39 C 0.8307(3) 0.1036(4) 0.44780(12) 0.0383(8) Uani 1 1 d . . . . .
H39 H 0.8764 0.0385 0.4582 0.046 Uiso 1 1 calc R . . . .
C40 C 0.7542(3) -0.0537(5) 0.32713(15) 0.0463(10) Uani 1 1 d . . . . .
H40A H 0.7233 0.0223 0.3102 0.070 Uiso 1 1 calc GR . . . .
H40B H 0.7472 -0.0489 0.3595 0.070 Uiso 1 1 calc GR . . . .
H40C H 0.7260 -0.1358 0.3134 0.070 Uiso 1 1 calc GR . . . .
C41 C 0.9116(2) 0.2357(4) 0.33825(12) 0.0352(7) Uani 1 1 d . . . . .
H41A H 0.8557 0.2124 0.3153 0.042 Uiso 1 1 calc R . . . .
H41B H 0.9050 0.3286 0.3477 0.042 Uiso 1 1 calc R . . . .
C43 C 1.0061(2) 0.1810(4) 0.41838(13) 0.0363(7) Uani 1 1 d . . . . .
C44 C 1.0890(4) 0.3654(6) 0.4576(2) 0.0686(15) Uani 1 1 d . . . . .
H44A H 1.1451 0.3343 0.4474 0.103 Uiso 1 1 calc GR . . . .
H44B H 1.0892 0.3343 0.4890 0.103 Uiso 1 1 calc GR . . . .
H44C H 1.0875 0.4624 0.4570 0.103 Uiso 1 1 calc GR . . . .
Cl3 Cl 0.60352(11) -0.27924(18) 0.01040(6) 0.0769(4) Uani 1 1 d . . . . .
C45 C 0.5000 -0.1807(8) 0.0000 0.0572(16) Uani 1 2 d S T P . .
H45A H 0.5009 -0.1230 -0.0270 0.069 Uiso 0.5 1 calc R . . . .
H45B H 0.4991 -0.1230 0.0270 0.069 Uiso 0.5 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 1.748(4) . ?
O1 C8 1.230(4) . ?
O2 N2 1.213(5) . ?
O3 N2 1.218(5) . ?
O4 C21 1.197(5) . ?
O5 C21 1.327(5) . ?
O5 C22 1.450(5) . ?
N1 H1 0.8600 . ?
N1 C1 1.391(5) . ?
N1 C8 1.356(5) . ?
N2 C19 1.507(5) . ?
C1 C2 1.378(5) . ?
C1 C6 1.403(5) . ?
C2 H2 0.9300 . ?
C2 C3 1.387(6) . ?
C3 H3 0.9300 . ?
C3 C4 1.384(7) . ?
C4 H4 0.9300 . ?
C4 C5 1.383(6) . ?
C5 H5 0.9300 . ?
C5 C6 1.394(5) . ?
C6 C7 1.481(5) . ?
C7 C8 1.506(4) . ?
C7 C9 1.343(5) . ?
C9 C10 1.517(5) . ?
C9 C18 1.503(5) . ?
C10 H10A 0.98(4) . ?
C10 H10B 1.03(4) . ?
C10 C11 1.557(5) . ?
C11 C12 1.549(5) . ?
C11 C19 1.538(5) . ?
C11 C21 1.550(5) . ?
C12 C13 1.386(6) . ?
C12 C17 1.388(6) . ?
C13 H13 0.9300 . ?
C13 C14 1.384(6) . ?
C14 H14 0.9300 . ?
C14 C15 1.377(7) . ?
C15 C16 1.377(7) . ?
C16 H16 0.9300 . ?
C16 C17 1.381(6) . ?
C17 H17 0.9300 . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
Cl2 C37 1.749(4) . ?
O6 C30 1.220(5) . ?
O7 N4 1.220(5) . ?
O8 N4 1.215(5) . ?
O9 C43 1.191(5) . ?
O10 C43 1.330(5) . ?
O10 C44 1.439(5) . ?
N3 H3A 0.8600 . ?
N3 C23 1.404(5) . ?
N3 C30 1.358(5) . ?
N4 C41 1.502(4) . ?
C23 C24 1.365(6) . ?
C23 C28 1.399(5) . ?
C24 H24 0.9300 . ?
C24 C25 1.392(6) . ?
C25 H25 0.9300 . ?
C25 C26 1.371(7) . ?
C26 H26 0.9300 . ?
C26 C27 1.392(6) . ?
C27 H27 0.9300 . ?
C27 C28 1.396(5) . ?
C28 C29 1.479(5) . ?
C29 C30 1.516(4) . ?
C29 C31 1.345(5) . ?
C31 C32 1.514(5) . ?
C31 C40 1.502(4) . ?
C32 H32A 0.9700 . ?
C32 H32B 0.9700 . ?
C32 C33 1.553(5) . ?
C33 C34 1.547(4) . ?
C33 C41 1.537(5) . ?
C33 C43 1.549(4) . ?
C34 C35 1.383(5) . ?
C34 C39 1.390(5) . ?
C35 H35 0.9300 . ?
C35 C36 1.403(6) . ?
C36 H36 0.9300 . ?
C36 C37 1.356(7) . ?
C37 C38 1.377(7) . ?
C38 H38 0.9300 . ?
C38 C39 1.387(5) . ?
C39 H39 0.9300 . ?
C40 H40A 0.9600 . ?
C40 H40B 0.9600 . ?
C40 H40C 0.9600 . ?
C41 H41A 0.9700 . ?
C41 H41B 0.9700 . ?
C44 H44A 0.9600 . ?
C44 H44B 0.9600 . ?
C44 H44C 0.9600 . ?
Cl3 C45 1.758(5) . ?
C45 Cl3 1.758(5) 2_655 ?
C45 H45A 0.9700 . ?
C45 H45B 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
C21 O5 C22 116.8(3) . . ?
C1 N1 H1 124.0 . . ?
C8 N1 H1 124.0 . . ?
C8 N1 C1 112.0(3) . . ?
O2 N2 O3 123.7(4) . . ?
O2 N2 C19 116.9(4) . . ?
O3 N2 C19 119.3(3) . . ?
N1 C1 C6 109.1(3) . . ?
C2 C1 N1 128.0(4) . . ?
C2 C1 C6 122.9(4) . . ?
C1 C2 H2 121.0 . . ?
C1 C2 C3 118.0(4) . . ?
C3 C2 H2 121.0 . . ?
C2 C3 H3 119.9 . . ?
C4 C3 C2 120.1(4) . . ?
C4 C3 H3 119.9 . . ?
C3 C4 H4 119.1 . . ?
C5 C4 C3 121.7(4) . . ?
C5 C4 H4 119.1 . . ?
C4 C5 H5 120.4 . . ?
C4 C5 C6 119.3(4) . . ?
C6 C5 H5 120.4 . . ?
C1 C6 C7 107.4(3) . . ?
C5 C6 C1 117.9(3) . . ?
C5 C6 C7 134.6(4) . . ?
C6 C7 C8 104.4(3) . . ?
C9 C7 C6 130.2(3) . . ?
C9 C7 C8 125.4(3) . . ?
O1 C8 N1 123.5(3) . . ?
O1 C8 C7 129.4(3) . . ?
N1 C8 C7 107.1(3) . . ?
C7 C9 C10 122.8(3) . . ?
C7 C9 C18 121.4(3) . . ?
C18 C9 C10 115.7(3) . . ?
C9 C10 H10A 108(2) . . ?
C9 C10 H10B 106(2) . . ?
C9 C10 C11 116.8(3) . . ?
H10A C10 H10B 104(3) . . ?
C11 C10 H10A 112(3) . . ?
C11 C10 H10B 109(3) . . ?
C12 C11 C10 111.6(3) . . ?
C12 C11 C21 101.2(3) . . ?
C19 C11 C10 112.2(3) . . ?
C19 C11 C12 113.2(3) . . ?
C19 C11 C21 107.8(3) . . ?
C21 C11 C10 110.3(3) . . ?
C13 C12 C11 122.7(4) . . ?
C13 C12 C17 117.6(4) . . ?
C17 C12 C11 119.6(4) . . ?
C12 C13 H13 119.3 . . ?
C14 C13 C12 121.5(4) . . ?
C14 C13 H13 119.3 . . ?
C13 C14 H14 120.4 . . ?
C15 C14 C13 119.2(4) . . ?
C15 C14 H14 120.4 . . ?
C14 C15 Cl1 119.9(4) . . ?
C14 C15 C16 120.9(4) . . ?
C16 C15 Cl1 119.2(4) . . ?
C15 C16 H16 120.5 . . ?
C15 C16 C17 118.9(4) . . ?
C17 C16 H16 120.5 . . ?
C12 C17 H17 119.1 . . ?
C16 C17 C12 121.9(4) . . ?
C16 C17 H17 119.1 . . ?
C9 C18 H18A 109.5 . . ?
C9 C18 H18B 109.5 . . ?
C9 C18 H18C 109.5 . . ?
H18A C18 H18B 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
N2 C19 C11 114.7(3) . . ?
N2 C19 H19A 108.6 . . ?
N2 C19 H19B 108.6 . . ?
C11 C19 H19A 108.6 . . ?
C11 C19 H19B 108.6 . . ?
H19A C19 H19B 107.6 . . ?
O4 C21 O5 124.5(4) . . ?
O4 C21 C11 123.4(4) . . ?
O5 C21 C11 112.0(3) . . ?
O5 C22 H22A 109.5 . . ?
O5 C22 H22B 109.5 . . ?
O5 C22 H22C 109.5 . . ?
H22A C22 H22B 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C43 O10 C44 116.2(4) . . ?
C23 N3 H3A 123.9 . . ?
C30 N3 H3A 123.9 . . ?
C30 N3 C23 112.2(3) . . ?
O7 N4 C41 118.4(3) . . ?
O8 N4 O7 124.0(4) . . ?
O8 N4 C41 117.6(3) . . ?
C24 C23 N3 127.4(4) . . ?
C24 C23 C28 123.7(4) . . ?
C28 C23 N3 108.9(3) . . ?
C23 C24 H24 121.4 . . ?
C23 C24 C25 117.2(4) . . ?
C25 C24 H24 121.4 . . ?
C24 C25 H25 119.5 . . ?
C26 C25 C24 121.1(4) . . ?
C26 C25 H25 119.5 . . ?
C25 C26 H26 119.4 . . ?
C25 C26 C27 121.2(4) . . ?
C27 C26 H26 119.4 . . ?
C26 C27 H27 120.5 . . ?
C26 C27 C28 119.1(4) . . ?
C28 C27 H27 120.5 . . ?
C23 C28 C29 107.6(3) . . ?
C27 C28 C23 117.8(4) . . ?
C27 C28 C29 134.5(3) . . ?
C28 C29 C30 104.8(3) . . ?
C31 C29 C28 130.3(3) . . ?
C31 C29 C30 124.9(3) . . ?
O6 C30 N3 123.9(3) . . ?
O6 C30 C29 129.6(3) . . ?
N3 C30 C29 106.4(3) . . ?
C29 C31 C32 122.1(3) . . ?
C29 C31 C40 121.9(3) . . ?
C40 C31 C32 116.0(3) . . ?
C31 C32 H32A 108.6 . . ?
C31 C32 H32B 108.6 . . ?
C31 C32 C33 114.7(3) . . ?
H32A C32 H32B 107.6 . . ?
C33 C32 H32A 108.6 . . ?
C33 C32 H32B 108.6 . . ?
C34 C33 C32 112.7(3) . . ?
C34 C33 C43 104.3(3) . . ?
C41 C33 C32 112.2(3) . . ?
C41 C33 C34 109.7(3) . . ?
C41 C33 C43 109.3(3) . . ?
C43 C33 C32 108.3(3) . . ?
C35 C34 C33 124.0(3) . . ?
C35 C34 C39 118.8(3) . . ?
C39 C34 C33 117.1(3) . . ?
C34 C35 H35 119.7 . . ?
C34 C35 C36 120.5(4) . . ?
C36 C35 H35 119.7 . . ?
C35 C36 H36 120.5 . . ?
C37 C36 C35 119.0(4) . . ?
C37 C36 H36 120.5 . . ?
C36 C37 Cl2 119.5(3) . . ?
C36 C37 C38 122.2(4) . . ?
C38 C37 Cl2 118.3(3) . . ?
C37 C38 H38 120.7 . . ?
C37 C38 C39 118.7(4) . . ?
C39 C38 H38 120.7 . . ?
C34 C39 H39 119.6 . . ?
C38 C39 C34 120.9(4) . . ?
C38 C39 H39 119.6 . . ?
C31 C40 H40A 109.5 . . ?
C31 C40 H40B 109.5 . . ?
C31 C40 H40C 109.5 . . ?
H40A C40 H40B 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?
N4 C41 C33 112.8(3) . . ?
N4 C41 H41A 109.0 . . ?
N4 C41 H41B 109.0 . . ?
C33 C41 H41A 109.0 . . ?
C33 C41 H41B 109.0 . . ?
H41A C41 H41B 107.8 . . ?
O9 C43 O10 125.3(4) . . ?
O9 C43 C33 125.0(4) . . ?
O10 C43 C33 109.6(3) . . ?
O10 C44 H44A 109.5 . . ?
O10 C44 H44B 109.5 . . ?
O10 C44 H44C 109.5 . . ?
H44A C44 H44B 109.5 . . ?
H44A C44 H44C 109.5 . . ?
H44B C44 H44C 109.5 . . ?
Cl3 C45 Cl3 112.6(4) . 2_655 ?
Cl3 C45 H45A 109.1 . . ?
Cl3 C45 H45A 109.1 2_655 . ?
Cl3 C45 H45B 109.1 2_655 . ?
Cl3 C45 H45B 109.1 . . ?
H45A C45 H45B 107.8 . . ?

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 C15 C16 C17 -179.2(3) . . . . ?
O2 N2 C19 C11 -141.8(4) . . . . ?
O3 N2 C19 C11 41.7(5) . . . . ?
N1 C1 C2 C3 178.5(4) . . . . ?
N1 C1 C6 C5 -178.8(4) . . . . ?
N1 C1 C6 C7 -0.7(4) . . . . ?
C1 N1 C8 O1 178.8(4) . . . . ?
C1 N1 C8 C7 -0.6(5) . . . . ?
C1 C2 C3 C4 0.0(7) . . . . ?
C1 C6 C7 C8 0.4(4) . . . . ?
C1 C6 C7 C9 -179.8(4) . . . . ?
C2 C1 C6 C5 0.0(6) . . . . ?
C2 C1 C6 C7 178.0(4) . . . . ?
C2 C3 C4 C5 0.0(8) . . . . ?
C3 C4 C5 C6 -0.1(7) . . . . ?
C4 C5 C6 C1 0.1(6) . . . . ?
C4 C5 C6 C7 -177.3(4) . . . . ?
C5 C6 C7 C8 178.0(4) . . . . ?
C5 C6 C7 C9 -2.1(7) . . . . ?
C6 C1 C2 C3 0.0(7) . . . . ?
C6 C7 C8 O1 -179.2(4) . . . . ?
C6 C7 C8 N1 0.1(4) . . . . ?
C6 C7 C9 C10 -179.5(4) . . . . ?
C6 C7 C9 C18 -2.7(6) . . . . ?
C7 C9 C10 C11 -108.1(4) . . . . ?
C8 N1 C1 C2 -177.9(4) . . . . ?
C8 N1 C1 C6 0.9(5) . . . . ?
C8 C7 C9 C10 0.3(6) . . . . ?
C8 C7 C9 C18 177.1(4) . . . . ?
C9 C7 C8 O1 1.0(7) . . . . ?
C9 C7 C8 N1 -179.8(4) . . . . ?
C9 C10 C11 C12 178.1(3) . . . . ?
C9 C10 C11 C19 49.9(4) . . . . ?
C9 C10 C11 C21 -70.3(4) . . . . ?
C10 C11 C12 C13 8.2(5) . . . . ?
C10 C11 C12 C17 -175.9(3) . . . . ?
C10 C11 C19 N2 62.3(4) . . . . ?
C10 C11 C21 O4 -36.6(5) . . . . ?
C10 C11 C21 O5 147.6(3) . . . . ?
C11 C12 C13 C14 175.1(4) . . . . ?
C11 C12 C17 C16 -175.1(3) . . . . ?
C12 C11 C19 N2 -65.0(4) . . . . ?
C12 C11 C21 O4 81.6(4) . . . . ?
C12 C11 C21 O5 -94.2(3) . . . . ?
C12 C13 C14 C15 0.5(7) . . . . ?
C13 C12 C17 C16 1.0(6) . . . . ?
C13 C14 C15 Cl1 179.3(4) . . . . ?
C13 C14 C15 C16 -0.1(7) . . . . ?
C14 C15 C16 C17 0.2(7) . . . . ?
C15 C16 C17 C12 -0.6(6) . . . . ?
C17 C12 C13 C14 -0.9(6) . . . . ?
C18 C9 C10 C11 75.0(4) . . . . ?
C19 C11 C12 C13 135.8(4) . . . . ?
C19 C11 C12 C17 -48.2(5) . . . . ?
C19 C11 C21 O4 -159.4(4) . . . . ?
C19 C11 C21 O5 24.8(4) . . . . ?
C21 C11 C12 C13 -109.1(4) . . . . ?
C21 C11 C12 C17 66.8(4) . . . . ?
C21 C11 C19 N2 -176.1(3) . . . . ?
C22 O5 C21 O4 -7.1(6) . . . . ?
C22 O5 C21 C11 168.7(3) . . . . ?
Cl2 C37 C38 C39 -179.0(3) . . . . ?
O7 N4 C41 C33 -45.1(5) . . . . ?
O8 N4 C41 C33 137.1(4) . . . . ?
N3 C23 C24 C25 -178.5(4) . . . . ?
N3 C23 C28 C27 178.8(4) . . . . ?
N3 C23 C28 C29 1.6(4) . . . . ?
C23 N3 C30 O6 -178.4(4) . . . . ?
C23 N3 C30 C29 0.6(5) . . . . ?
C23 C24 C25 C26 -1.0(7) . . . . ?
C23 C28 C29 C30 -1.2(4) . . . . ?
C23 C28 C29 C31 179.5(4) . . . . ?
C24 C23 C28 C27 -1.6(6) . . . . ?
C24 C23 C28 C29 -178.8(4) . . . . ?
C24 C25 C26 C27 -0.4(8) . . . . ?
C25 C26 C27 C28 0.8(7) . . . . ?
C26 C27 C28 C23 0.2(6) . . . . ?
C26 C27 C28 C29 176.5(4) . . . . ?
C27 C28 C29 C30 -177.7(4) . . . . ?
C27 C28 C29 C31 2.9(7) . . . . ?
C28 C23 C24 C25 2.0(6) . . . . ?
C28 C29 C30 O6 179.3(4) . . . . ?
C28 C29 C30 N3 0.4(4) . . . . ?
C28 C29 C31 C32 -177.6(4) . . . . ?
C28 C29 C31 C40 1.9(6) . . . . ?
C29 C31 C32 C33 110.4(4) . . . . ?
C30 N3 C23 C24 179.0(4) . . . . ?
C30 N3 C23 C28 -1.4(5) . . . . ?
C30 C29 C31 C32 3.2(6) . . . . ?
C30 C29 C31 C40 -177.4(4) . . . . ?
C31 C29 C30 O6 -1.3(7) . . . . ?
C31 C29 C30 N3 179.8(4) . . . . ?
C31 C32 C33 C34 80.5(3) . . . . ?
C31 C32 C33 C41 -44.0(4) . . . . ?
C31 C32 C33 C43 -164.7(3) . . . . ?
C32 C33 C34 C35 -126.4(4) . . . . ?
C32 C33 C34 C39 57.5(4) . . . . ?
C32 C33 C41 N4 -60.9(4) . . . . ?
C32 C33 C43 O9 -9.3(5) . . . . ?
C32 C33 C43 O10 173.9(3) . . . . ?
C33 C34 C35 C36 -175.5(4) . . . . ?
C33 C34 C39 C38 176.5(3) . . . . ?
C34 C33 C41 N4 173.0(3) . . . . ?
C34 C33 C43 O9 110.9(4) . . . . ?
C34 C33 C43 O10 -65.8(4) . . . . ?
C34 C35 C36 C37 -0.1(7) . . . . ?
C35 C34 C39 C38 0.2(6) . . . . ?
C35 C36 C37 Cl2 179.6(3) . . . . ?
C35 C36 C37 C38 -1.0(7) . . . . ?
C36 C37 C38 C39 1.7(7) . . . . ?
C37 C38 C39 C34 -1.2(6) . . . . ?
C39 C34 C35 C36 0.5(6) . . . . ?
C40 C31 C32 C33 -69.1(4) . . . . ?
C41 C33 C34 C35 -0.6(5) . . . . ?
C41 C33 C34 C39 -176.6(3) . . . . ?
C41 C33 C43 O9 -131.9(4) . . . . ?
C41 C33 C43 O10 51.4(4) . . . . ?
C43 C33 C34 C35 116.4(4) . . . . ?
C43 C33 C34 C39 -59.7(4) . . . . ?
C43 C33 C41 N4 59.2(4) . . . . ?
C44 O10 C43 O9 7.8(7) . . . . ?
C44 O10 C43 C33 -175.5(4) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_database_code_depnum_ccdc_archive 'CCDC 1007906'
