# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_cd15125
_database_code_depnum_ccdc_archive 'CCDC 1437092'
_audit_update_record             
;
2015-11-16 deposited with the CCDC.
2016-01-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C51 H42 Cl4 N4 O7'
_chemical_formula_weight         964.68

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                   11.980(3)
_cell_length_b                   13.777(3)
_cell_length_c                   14.492(3)
_cell_angle_alpha                83.296(5)
_cell_angle_beta                 80.970(5)
_cell_angle_gamma                87.489(5)
_cell_volume                     2345.2(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1413
_cell_measurement_theta_min      4.355
_cell_measurement_theta_max      41.931

_exptl_crystal_description       prismatic
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.366
_exptl_crystal_F_000             1000
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.180
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    0.310
_shelx_estimated_absorpt_T_min   0.946
_shelx_estimated_absorpt_T_max   0.976
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6048
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13088
_diffrn_reflns_av_unetI/netI     0.1060
_diffrn_reflns_av_R_equivalents  0.0533
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         1.947
_diffrn_reflns_theta_max         25.049
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.977
_reflns_number_total             8312
_reflns_number_gt                4872
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_structure_solution    'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_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)+(0.1042P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8312
_refine_ls_number_parameters     615
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1326
_refine_ls_R_factor_gt           0.0787
_refine_ls_wR_factor_ref         0.2211
_refine_ls_wR_factor_gt          0.1858
_refine_ls_goodness_of_fit_ref   1.005
_refine_ls_restrained_S_all      1.005
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
H1 H -0.103(3) 0.024(3) 0.555(3) 0.036(11) Uiso 1 1 d . . . . .
Cl1 Cl 0.00763(13) 0.41678(9) 0.38954(11) 0.0738(5) Uani 1 1 d . . . . .
Cl2 Cl -0.20937(12) 0.17605(12) 0.21784(10) 0.0766(5) Uani 1 1 d . . . . .
Cl3 Cl 0.85728(12) 0.03737(9) 1.01095(11) 0.0728(4) Uani 1 1 d . . . . .
Cl4 Cl 0.42872(12) 0.17828(13) 1.06695(11) 0.0886(5) Uani 1 1 d . . . . .
N1 N -0.0865(3) 0.0854(3) 0.5440(3) 0.0455(10) Uani 1 1 d . . . . .
N2 N 0.1492(3) 0.3457(3) 0.6553(3) 0.0399(9) Uani 1 1 d . . . . .
N3 N 0.7452(3) 0.3328(3) 0.8164(3) 0.0531(11) Uani 1 1 d . . . . .
N4 N 1.1373(3) 0.1515(3) 0.8068(3) 0.0409(9) Uani 1 1 d . . . . .
O1 O 0.0019(3) 0.0892(2) 0.6722(2) 0.0573(9) Uani 1 1 d . . . . .
O2 O 0.1632(3) 0.1143(2) 0.4415(2) 0.0567(9) Uani 1 1 d . . . . .
O3 O 0.4213(3) 0.4926(3) 0.8798(3) 0.0751(11) Uani 1 1 d . . . . .
O4 O 0.9173(3) 0.3656(3) 0.7295(3) 0.0661(10) Uani 1 1 d . . . . .
O5 O 0.8895(3) 0.3639(2) 0.9782(3) 0.0629(10) Uani 1 1 d . . . . .
O6 O 1.5875(3) 0.0566(2) 0.6834(3) 0.0640(10) Uani 1 1 d . . . . .
O7 O 0.6616(5) 0.4052(5) 0.6392(4) 0.146(2) Uani 1 1 d . . . . .
C1 C -0.0520(4) 0.3041(3) 0.3892(4) 0.0497(12) Uani 1 1 d . . . . .
C2 C -0.1035(4) 0.2875(4) 0.3136(4) 0.0551(12) Uani 1 1 d . . . . .
H2 H -0.1063 0.3354 0.2631 0.066 Uiso 1 1 calc R U . . .
C3 C -0.1504(4) 0.1977(4) 0.3158(3) 0.0534(13) Uani 1 1 d . . . . .
C4 C -0.1510(4) 0.1254(3) 0.3886(3) 0.0479(12) Uani 1 1 d . . . . .
H4 H -0.1849 0.0660 0.3887 0.057 Uiso 1 1 calc R U . . .
C5 C -0.0987(4) 0.1451(3) 0.4620(3) 0.0412(10) Uani 1 1 d . . . . .
C6 C -0.0483(3) 0.2339(3) 0.4632(3) 0.0412(10) Uani 1 1 d . . . . .
C7 C 0.0059(4) 0.2295(3) 0.5504(3) 0.0402(10) Uani 1 1 d . . . . .
H7 H -0.0309 0.2781 0.5901 0.048 Uiso 1 1 calc R U . . .
C8 C -0.0237(4) 0.1272(3) 0.5979(3) 0.0435(11) Uani 1 1 d . . . . .
C9 C 0.1328(3) 0.2462(3) 0.5302(3) 0.0375(10) Uani 1 1 d . . . . .
C10 C 0.1881(4) 0.2995(3) 0.5809(3) 0.0374(10) Uani 1 1 d . . . . .
H10 H 0.2654 0.3043 0.5604 0.045 Uiso 1 1 calc R U . . .
C11 C 0.1982(4) 0.1916(3) 0.4610(3) 0.0428(11) Uani 1 1 d . . . . .
C12 C 0.3102(4) 0.2270(3) 0.4112(3) 0.0432(11) Uani 1 1 d . . . . .
C13 C 0.3955(4) 0.1591(4) 0.3857(4) 0.0622(14) Uani 1 1 d . . . . .
H13 H 0.3838 0.0929 0.4039 0.075 Uiso 1 1 calc R U . . .
C14 C 0.4969(5) 0.1885(5) 0.3338(5) 0.089(2) Uani 1 1 d . . . . .
H14 H 0.5536 0.1425 0.3176 0.106 Uiso 1 1 calc R U . . .
C15 C 0.5141(5) 0.2855(5) 0.3060(5) 0.0854(19) Uani 1 1 d . . . . .
H15 H 0.5826 0.3055 0.2708 0.102 Uiso 1 1 calc R U . . .
C16 C 0.4308(5) 0.3536(4) 0.3299(4) 0.0723(16) Uani 1 1 d . . . . .
H16 H 0.4429 0.4196 0.3107 0.087 Uiso 1 1 calc R U . . .
C17 C 0.3292(4) 0.3245(3) 0.3823(3) 0.0506(12) Uani 1 1 d . . . . .
H17 H 0.2731 0.3711 0.3982 0.061 Uiso 1 1 calc R U . . .
C18 C 0.2186(4) 0.3852(3) 0.7117(3) 0.0379(10) Uani 1 1 d . . . . .
C19 C 0.1703(4) 0.4464(3) 0.7759(3) 0.0446(11) Uani 1 1 d . . . . .
H19 H 0.0937 0.4627 0.7802 0.054 Uiso 1 1 calc R U . . .
C20 C 0.2338(4) 0.4840(3) 0.8341(3) 0.0526(12) Uani 1 1 d . . . . .
H20 H 0.2003 0.5249 0.8779 0.063 Uiso 1 1 calc R U . . .
C21 C 0.3484(4) 0.4604(3) 0.8267(3) 0.0513(12) Uani 1 1 d . . . . .
C22 C 0.3966(4) 0.3992(3) 0.7628(3) 0.0515(12) Uani 1 1 d . . . . .
H22 H 0.4735 0.3837 0.7575 0.062 Uiso 1 1 calc R U . . .
C23 C 0.3315(4) 0.3605(3) 0.7063(3) 0.0454(11) Uani 1 1 d . . . . .
H23 H 0.3643 0.3174 0.6643 0.054 Uiso 1 1 calc R U . . .
C24 C 0.3790(6) 0.5575(5) 0.9448(5) 0.116(3) Uani 1 1 d . . . . .
H24A H 0.3395 0.6110 0.9143 0.174 Uiso 1 1 calc R U . . .
H24B H 0.4404 0.5820 0.9699 0.174 Uiso 1 1 calc R U . . .
H24C H 0.3279 0.5240 0.9950 0.174 Uiso 1 1 calc R U . . .
C25 C 0.7552(4) 0.1243(3) 0.9837(3) 0.0458(11) Uani 1 1 d . . . . .
C26 C 0.6464(4) 0.1173(4) 1.0318(4) 0.0560(13) Uani 1 1 d . . . . .
H26 H 0.6278 0.0676 1.0803 0.067 Uiso 1 1 calc R U . . .
C27 C 0.5659(4) 0.1851(4) 1.0066(3) 0.0528(12) Uani 1 1 d . . . . .
C28 C 0.5886(4) 0.2602(3) 0.9354(3) 0.0486(12) Uani 1 1 d . . . . .
H28 H 0.5329 0.3050 0.9187 0.058 Uiso 1 1 calc R U . . .
C29 C 0.6988(4) 0.2650(3) 0.8902(3) 0.0435(11) Uani 1 1 d . . . . .
C30 C 0.7836(4) 0.1995(3) 0.9139(3) 0.0400(10) Uani 1 1 d . . . . .
C31 C 0.8929(3) 0.2257(3) 0.8523(3) 0.0405(10) Uani 1 1 d . . . . .
H31 H 0.9141 0.1738 0.8115 0.049 Uiso 1 1 calc R U . . .
C32 C 0.8578(4) 0.3168(3) 0.7918(3) 0.0478(11) Uani 1 1 d . . . . .
C33 C 0.9915(4) 0.2404(3) 0.9024(3) 0.0372(10) Uani 1 1 d . . . . .
C34 C 1.0986(4) 0.2055(3) 0.8766(3) 0.0402(10) Uani 1 1 d . . . . .
H34 H 1.1519 0.2213 0.9122 0.048 Uiso 1 1 calc R U . . .
C35 C 0.9707(4) 0.3053(3) 0.9754(3) 0.0429(11) Uani 1 1 d . . . . .
C36 C 1.0471(4) 0.3004(3) 1.0478(3) 0.0476(11) Uani 1 1 d . . . . .
C37 C 1.0819(5) 0.3867(4) 1.0742(4) 0.0660(15) Uani 1 1 d . . . . .
H37 H 1.0596 0.4470 1.0459 0.079 Uiso 1 1 calc R U . . .
C38 C 1.1506(6) 0.3815(6) 1.1439(5) 0.097(2) Uani 1 1 d . . . . .
H38 H 1.1774 0.4385 1.1602 0.116 Uiso 1 1 calc R U . . .
C39 C 1.1787(6) 0.2933(7) 1.1880(5) 0.096(2) Uani 1 1 d . . . . .
H39 H 1.2233 0.2907 1.2354 0.116 Uiso 1 1 calc R U . . .
C40 C 1.1429(5) 0.2093(6) 1.1641(4) 0.0843(19) Uani 1 1 d . . . . .
H40 H 1.1627 0.1496 1.1951 0.101 Uiso 1 1 calc R U . . .
C41 C 1.0771(4) 0.2120(4) 1.0939(4) 0.0636(14) Uani 1 1 d . . . . .
H41 H 1.0528 0.1540 1.0775 0.076 Uiso 1 1 calc R U . . .
C42 C 1.2523(4) 0.1258(3) 0.7810(3) 0.0385(10) Uani 1 1 d . . . . .
C43 C 1.2861(4) 0.0960(3) 0.6931(3) 0.0460(11) Uani 1 1 d . . . . .
H43 H 1.2328 0.0912 0.6537 0.055 Uiso 1 1 calc R U . . .
C44 C 1.3979(4) 0.0735(3) 0.6631(3) 0.0525(12) Uani 1 1 d . . . . .
H44 H 1.4190 0.0538 0.6034 0.063 Uiso 1 1 calc R U . . .
C45 C 1.4791(4) 0.0796(3) 0.7195(3) 0.0477(11) Uani 1 1 d . . . . .
C46 C 1.4459(4) 0.1080(3) 0.8078(3) 0.0502(12) Uani 1 1 d . . . . .
H46 H 1.4992 0.1118 0.8475 0.060 Uiso 1 1 calc R U . . .
C47 C 1.3335(4) 0.1308(3) 0.8377(3) 0.0497(12) Uani 1 1 d . . . . .
H47 H 1.3123 0.1500 0.8975 0.060 Uiso 1 1 calc R U . . .
C48 C 1.6701(5) 0.0508(5) 0.7429(5) 0.0861(19) Uani 1 1 d . . . . .
H48A H 1.6790 0.1143 0.7617 0.129 Uiso 1 1 calc R U . . .
H48B H 1.7408 0.0285 0.7101 0.129 Uiso 1 1 calc R U . . .
H48C H 1.6471 0.0058 0.7977 0.129 Uiso 1 1 calc R U . . .
C49 C 0.6280(8) 0.2778(6) 0.5520(8) 0.187(6) Uani 1 1 d . . . . .
H49A H 0.6545 0.2332 0.6004 0.280 Uiso 1 1 calc R U . . .
H49B H 0.6628 0.2608 0.4915 0.280 Uiso 1 1 calc R U . . .
H49C H 0.5474 0.2740 0.5573 0.280 Uiso 1 1 calc R U . . .
C50 C 0.6572(5) 0.3765(5) 0.5623(5) 0.087(2) Uani 1 1 d . . . . .
C51 C 0.6751(9) 0.4438(5) 0.4803(6) 0.135(3) Uani 1 1 d . . . . .
H51A H 0.6111 0.4881 0.4791 0.203 Uiso 1 1 calc R U . . .
H51B H 0.6845 0.4090 0.4258 0.203 Uiso 1 1 calc R U . . .
H51C H 0.7418 0.4799 0.4802 0.203 Uiso 1 1 calc R U . . .
H2A H 0.080(4) 0.352(3) 0.669(3) 0.034(12) Uiso 1 1 d . . . . .
H4A H 1.099(4) 0.138(3) 0.766(3) 0.043(13) Uiso 1 1 d . . . . .
H3 H 0.717(5) 0.373(4) 0.785(4) 0.068(19) Uiso 1 1 d . . . . .


_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 C1 1.738(4) . ?
Cl2 C3 1.742(5) . ?
Cl3 C25 1.732(5) . ?
Cl4 C27 1.738(5) . ?
N1 C8 1.355(5) . ?
N1 C5 1.388(6) . ?
N1 H1 0.87(4) . ?
N2 C10 1.327(5) . ?
N2 C18 1.418(5) . ?
N2 H2A 0.83(4) . ?
N3 C32 1.355(6) . ?
N3 C29 1.397(6) . ?
N3 H3 0.77(5) . ?
N4 C34 1.338(5) . ?
N4 C42 1.410(5) . ?
N4 H4A 0.84(4) . ?
O1 C8 1.219(5) . ?
O2 C11 1.239(5) . ?
O3 C21 1.369(5) . ?
O3 C24 1.397(7) . ?
O4 C32 1.215(5) . ?
O5 C35 1.235(5) . ?
O6 C45 1.360(5) . ?
O6 C48 1.406(7) . ?
O7 C50 1.235(8) . ?
C1 C6 1.363(6) . ?
C1 C2 1.385(6) . ?
C2 C3 1.377(7) . ?
C2 H2 0.9300 . ?
C3 C4 1.363(7) . ?
C4 C5 1.373(6) . ?
C4 H4 0.9300 . ?
C5 C6 1.391(6) . ?
C6 C7 1.502(6) . ?
C7 C8 1.524(6) . ?
C7 C9 1.525(6) . ?
C7 H7 0.9800 . ?
C9 C10 1.356(5) . ?
C9 C11 1.437(6) . ?
C10 H10 0.9300 . ?
C11 C12 1.493(6) . ?
C12 C17 1.378(6) . ?
C12 C13 1.391(7) . ?
C13 C14 1.375(8) . ?
C13 H13 0.9300 . ?
C14 C15 1.364(8) . ?
C14 H14 0.9300 . ?
C15 C16 1.372(8) . ?
C15 H15 0.9300 . ?
C16 C17 1.378(7) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 C23 1.373(6) . ?
C18 C19 1.373(6) . ?
C19 C20 1.377(6) . ?
C19 H19 0.9300 . ?
C20 C21 1.387(7) . ?
C20 H20 0.9300 . ?
C21 C22 1.369(7) . ?
C22 C23 1.380(6) . ?
C22 H22 0.9300 . ?
C23 H23 0.9300 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?
C25 C30 1.374(6) . ?
C25 C26 1.380(7) . ?
C26 C27 1.374(7) . ?
C26 H26 0.9300 . ?
C27 C28 1.376(7) . ?
C28 C29 1.379(6) . ?
C28 H28 0.9300 . ?
C29 C30 1.386(6) . ?
C30 C31 1.496(6) . ?
C31 C33 1.513(6) . ?
C31 C32 1.528(6) . ?
C31 H31 0.9800 . ?
C33 C34 1.362(6) . ?
C33 C35 1.449(6) . ?
C34 H34 0.9300 . ?
C35 C36 1.490(6) . ?
C36 C41 1.381(7) . ?
C36 C37 1.391(7) . ?
C37 C38 1.393(8) . ?
C37 H37 0.9300 . ?
C38 C39 1.360(10) . ?
C38 H38 0.9300 . ?
C39 C40 1.351(9) . ?
C39 H39 0.9300 . ?
C40 C41 1.378(8) . ?
C40 H40 0.9300 . ?
C41 H41 0.9300 . ?
C42 C47 1.378(6) . ?
C42 C43 1.379(6) . ?
C43 C44 1.375(6) . ?
C43 H43 0.9300 . ?
C44 C45 1.377(7) . ?
C44 H44 0.9300 . ?
C45 C46 1.375(6) . ?
C46 C47 1.382(6) . ?
C46 H46 0.9300 . ?
C47 H47 0.9300 . ?
C48 H48A 0.9600 . ?
C48 H48B 0.9600 . ?
C48 H48C 0.9600 . ?
C49 C50 1.449(10) . ?
C49 H49A 0.9600 . ?
C49 H49B 0.9600 . ?
C49 H49C 0.9600 . ?
C50 C51 1.414(9) . ?
C51 H51A 0.9600 . ?
C51 H51B 0.9600 . ?
C51 H51C 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
C8 N1 C5 112.0(4) . . ?
C8 N1 H1 122(3) . . ?
C5 N1 H1 125(3) . . ?
C10 N2 C18 124.3(4) . . ?
C10 N2 H2A 117(3) . . ?
C18 N2 H2A 119(3) . . ?
C32 N3 C29 111.8(4) . . ?
C32 N3 H3 116(4) . . ?
C29 N3 H3 132(4) . . ?
C34 N4 C42 124.1(4) . . ?
C34 N4 H4A 124(3) . . ?
C42 N4 H4A 111(3) . . ?
C21 O3 C24 118.1(4) . . ?
C45 O6 C48 118.4(4) . . ?
C6 C1 C2 121.0(4) . . ?
C6 C1 Cl1 119.8(3) . . ?
C2 C1 Cl1 119.1(4) . . ?
C3 C2 C1 117.6(5) . . ?
C3 C2 H2 121.2 . . ?
C1 C2 H2 121.2 . . ?
C4 C3 C2 123.9(4) . . ?
C4 C3 Cl2 119.1(4) . . ?
C2 C3 Cl2 117.1(4) . . ?
C3 C4 C5 116.4(4) . . ?
C3 C4 H4 121.8 . . ?
C5 C4 H4 121.8 . . ?
C4 C5 N1 128.5(4) . . ?
C4 C5 C6 122.5(4) . . ?
N1 C5 C6 109.0(4) . . ?
C1 C6 C5 118.6(4) . . ?
C1 C6 C7 132.5(4) . . ?
C5 C6 C7 108.9(4) . . ?
C6 C7 C8 101.9(3) . . ?
C6 C7 C9 113.5(4) . . ?
C8 C7 C9 113.2(4) . . ?
C6 C7 H7 109.3 . . ?
C8 C7 H7 109.3 . . ?
C9 C7 H7 109.3 . . ?
O1 C8 N1 125.1(4) . . ?
O1 C8 C7 126.8(4) . . ?
N1 C8 C7 108.0(4) . . ?
C10 C9 C11 118.6(4) . . ?
C10 C9 C7 124.0(4) . . ?
C11 C9 C7 116.9(3) . . ?
N2 C10 C9 130.1(4) . . ?
N2 C10 H10 114.9 . . ?
C9 C10 H10 114.9 . . ?
O2 C11 C9 120.9(4) . . ?
O2 C11 C12 118.7(4) . . ?
C9 C11 C12 120.4(4) . . ?
C17 C12 C13 118.3(4) . . ?
C17 C12 C11 122.2(4) . . ?
C13 C12 C11 119.2(4) . . ?
C14 C13 C12 120.9(5) . . ?
C14 C13 H13 119.5 . . ?
C12 C13 H13 119.5 . . ?
C15 C14 C13 119.8(6) . . ?
C15 C14 H14 120.1 . . ?
C13 C14 H14 120.1 . . ?
C14 C15 C16 120.2(6) . . ?
C14 C15 H15 119.9 . . ?
C16 C15 H15 119.9 . . ?
C15 C16 C17 120.2(5) . . ?
C15 C16 H16 119.9 . . ?
C17 C16 H16 119.9 . . ?
C12 C17 C16 120.5(5) . . ?
C12 C17 H17 119.7 . . ?
C16 C17 H17 119.7 . . ?
C23 C18 C19 119.4(4) . . ?
C23 C18 N2 121.7(4) . . ?
C19 C18 N2 118.9(4) . . ?
C18 C19 C20 120.9(4) . . ?
C18 C19 H19 119.5 . . ?
C20 C19 H19 119.5 . . ?
C19 C20 C21 119.3(4) . . ?
C19 C20 H20 120.3 . . ?
C21 C20 H20 120.3 . . ?
C22 C21 O3 114.7(4) . . ?
C22 C21 C20 119.8(4) . . ?
O3 C21 C20 125.5(4) . . ?
C21 C22 C23 120.2(4) . . ?
C21 C22 H22 119.9 . . ?
C23 C22 H22 119.9 . . ?
C18 C23 C22 120.3(4) . . ?
C18 C23 H23 119.8 . . ?
C22 C23 H23 119.8 . . ?
O3 C24 H24A 109.5 . . ?
O3 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
O3 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C30 C25 C26 120.8(4) . . ?
C30 C25 Cl3 119.4(4) . . ?
C26 C25 Cl3 119.8(4) . . ?
C27 C26 C25 118.7(5) . . ?
C27 C26 H26 120.6 . . ?
C25 C26 H26 120.6 . . ?
C26 C27 C28 123.1(5) . . ?
C26 C27 Cl4 119.5(4) . . ?
C28 C27 Cl4 117.4(4) . . ?
C27 C28 C29 116.1(4) . . ?
C27 C28 H28 122.0 . . ?
C29 C28 H28 122.0 . . ?
C28 C29 C30 123.2(4) . . ?
C28 C29 N3 128.2(4) . . ?
C30 C29 N3 108.6(4) . . ?
C25 C30 C29 118.1(4) . . ?
C25 C30 C31 132.2(4) . . ?
C29 C30 C31 109.7(4) . . ?
C30 C31 C33 116.0(4) . . ?
C30 C31 C32 101.7(4) . . ?
C33 C31 C32 114.1(3) . . ?
C30 C31 H31 108.2 . . ?
C33 C31 H31 108.2 . . ?
C32 C31 H31 108.2 . . ?
O4 C32 N3 124.5(5) . . ?
O4 C32 C31 127.2(4) . . ?
N3 C32 C31 108.2(4) . . ?
C34 C33 C35 119.1(4) . . ?
C34 C33 C31 124.2(4) . . ?
C35 C33 C31 116.3(4) . . ?
N4 C34 C33 128.7(4) . . ?
N4 C34 H34 115.7 . . ?
C33 C34 H34 115.7 . . ?
O5 C35 C33 120.2(4) . . ?
O5 C35 C36 120.1(4) . . ?
C33 C35 C36 119.8(4) . . ?
C41 C36 C37 119.4(5) . . ?
C41 C36 C35 121.1(4) . . ?
C37 C36 C35 119.4(4) . . ?
C36 C37 C38 119.0(6) . . ?
C36 C37 H37 120.5 . . ?
C38 C37 H37 120.5 . . ?
C39 C38 C37 120.2(6) . . ?
C39 C38 H38 119.9 . . ?
C37 C38 H38 119.9 . . ?
C40 C39 C38 121.0(6) . . ?
C40 C39 H39 119.5 . . ?
C38 C39 H39 119.5 . . ?
C39 C40 C41 120.1(6) . . ?
C39 C40 H40 119.9 . . ?
C41 C40 H40 119.9 . . ?
C40 C41 C36 120.2(6) . . ?
C40 C41 H41 119.9 . . ?
C36 C41 H41 119.9 . . ?
C47 C42 C43 117.9(4) . . ?
C47 C42 N4 123.8(4) . . ?
C43 C42 N4 118.3(4) . . ?
C44 C43 C42 120.7(4) . . ?
C44 C43 H43 119.7 . . ?
C42 C43 H43 119.7 . . ?
C43 C44 C45 121.3(4) . . ?
C43 C44 H44 119.3 . . ?
C45 C44 H44 119.3 . . ?
O6 C45 C46 124.5(4) . . ?
O6 C45 C44 117.0(4) . . ?
C46 C45 C44 118.5(4) . . ?
C45 C46 C47 120.1(4) . . ?
C45 C46 H46 120.0 . . ?
C47 C46 H46 120.0 . . ?
C42 C47 C46 121.6(4) . . ?
C42 C47 H47 119.2 . . ?
C46 C47 H47 119.2 . . ?
O6 C48 H48A 109.5 . . ?
O6 C48 H48B 109.5 . . ?
H48A C48 H48B 109.5 . . ?
O6 C48 H48C 109.5 . . ?
H48A C48 H48C 109.5 . . ?
H48B C48 H48C 109.5 . . ?
C50 C49 H49A 109.5 . . ?
C50 C49 H49B 109.5 . . ?
H49A C49 H49B 109.5 . . ?
C50 C49 H49C 109.5 . . ?
H49A C49 H49C 109.5 . . ?
H49B C49 H49C 109.5 . . ?
O7 C50 C51 119.1(8) . . ?
O7 C50 C49 123.1(8) . . ?
C51 C50 C49 117.7(8) . . ?
C50 C51 H51A 109.5 . . ?
C50 C51 H51B 109.5 . . ?
H51A C51 H51B 109.5 . . ?
C50 C51 H51C 109.5 . . ?
H51A C51 H51C 109.5 . . ?
H51B C51 H51C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 -0.1(7) . . . . ?
Cl1 C1 C2 C3 -179.7(4) . . . . ?
C1 C2 C3 C4 1.4(8) . . . . ?
C1 C2 C3 Cl2 -177.3(4) . . . . ?
C2 C3 C4 C5 -1.5(7) . . . . ?
Cl2 C3 C4 C5 177.1(3) . . . . ?
C3 C4 C5 N1 -179.7(4) . . . . ?
C3 C4 C5 C6 0.4(7) . . . . ?
C8 N1 C5 C4 176.1(5) . . . . ?
C8 N1 C5 C6 -4.0(5) . . . . ?
C2 C1 C6 C5 -0.9(7) . . . . ?
Cl1 C1 C6 C5 178.7(3) . . . . ?
C2 C1 C6 C7 176.3(5) . . . . ?
Cl1 C1 C6 C7 -4.1(7) . . . . ?
C4 C5 C6 C1 0.7(7) . . . . ?
N1 C5 C6 C1 -179.1(4) . . . . ?
C4 C5 C6 C7 -177.1(4) . . . . ?
N1 C5 C6 C7 3.1(5) . . . . ?
C1 C6 C7 C8 -178.5(5) . . . . ?
C5 C6 C7 C8 -1.1(5) . . . . ?
C1 C6 C7 C9 -56.5(6) . . . . ?
C5 C6 C7 C9 120.9(4) . . . . ?
C5 N1 C8 O1 -178.2(4) . . . . ?
C5 N1 C8 C7 3.2(5) . . . . ?
C6 C7 C8 O1 -179.8(5) . . . . ?
C9 C7 C8 O1 58.0(6) . . . . ?
C6 C7 C8 N1 -1.2(5) . . . . ?
C9 C7 C8 N1 -123.5(4) . . . . ?
C6 C7 C9 C10 140.1(4) . . . . ?
C8 C7 C9 C10 -104.3(5) . . . . ?
C6 C7 C9 C11 -48.2(5) . . . . ?
C8 C7 C9 C11 67.3(5) . . . . ?
C18 N2 C10 C9 168.9(4) . . . . ?
C11 C9 C10 N2 -170.9(4) . . . . ?
C7 C9 C10 N2 0.7(7) . . . . ?
C10 C9 C11 O2 149.5(4) . . . . ?
C7 C9 C11 O2 -22.6(6) . . . . ?
C10 C9 C11 C12 -30.4(6) . . . . ?
C7 C9 C11 C12 157.5(4) . . . . ?
O2 C11 C12 C17 140.7(4) . . . . ?
C9 C11 C12 C17 -39.3(6) . . . . ?
O2 C11 C12 C13 -33.6(6) . . . . ?
C9 C11 C12 C13 146.4(5) . . . . ?
C17 C12 C13 C14 0.7(8) . . . . ?
C11 C12 C13 C14 175.2(5) . . . . ?
C12 C13 C14 C15 -0.6(10) . . . . ?
C13 C14 C15 C16 0.2(11) . . . . ?
C14 C15 C16 C17 0.1(10) . . . . ?
C13 C12 C17 C16 -0.4(7) . . . . ?
C11 C12 C17 C16 -174.8(5) . . . . ?
C15 C16 C17 C12 0.0(8) . . . . ?
C10 N2 C18 C23 -14.5(6) . . . . ?
C10 N2 C18 C19 168.4(4) . . . . ?
C23 C18 C19 C20 0.8(7) . . . . ?
N2 C18 C19 C20 178.0(4) . . . . ?
C18 C19 C20 C21 0.7(7) . . . . ?
C24 O3 C21 C22 178.3(6) . . . . ?
C24 O3 C21 C20 -2.4(8) . . . . ?
C19 C20 C21 C22 -0.9(7) . . . . ?
C19 C20 C21 O3 179.9(5) . . . . ?
O3 C21 C22 C23 178.9(4) . . . . ?
C20 C21 C22 C23 -0.4(7) . . . . ?
C19 C18 C23 C22 -2.1(7) . . . . ?
N2 C18 C23 C22 -179.2(4) . . . . ?
C21 C22 C23 C18 1.9(7) . . . . ?
C30 C25 C26 C27 2.1(7) . . . . ?
Cl3 C25 C26 C27 -177.7(4) . . . . ?
C25 C26 C27 C28 0.0(7) . . . . ?
C25 C26 C27 Cl4 -179.4(4) . . . . ?
C26 C27 C28 C29 -0.8(7) . . . . ?
Cl4 C27 C28 C29 178.6(3) . . . . ?
C27 C28 C29 C30 -0.3(6) . . . . ?
C27 C28 C29 N3 -179.9(4) . . . . ?
C32 N3 C29 C28 177.9(4) . . . . ?
C32 N3 C29 C30 -1.7(5) . . . . ?
C26 C25 C30 C29 -3.1(6) . . . . ?
Cl3 C25 C30 C29 176.7(3) . . . . ?
C26 C25 C30 C31 179.0(4) . . . . ?
Cl3 C25 C30 C31 -1.2(7) . . . . ?
C28 C29 C30 C25 2.3(6) . . . . ?
N3 C29 C30 C25 -178.1(4) . . . . ?
C28 C29 C30 C31 -179.4(4) . . . . ?
N3 C29 C30 C31 0.2(5) . . . . ?
C25 C30 C31 C33 -56.5(6) . . . . ?
C29 C30 C31 C33 125.5(4) . . . . ?
C25 C30 C31 C32 179.1(4) . . . . ?
C29 C30 C31 C32 1.1(4) . . . . ?
C29 N3 C32 O4 179.7(4) . . . . ?
C29 N3 C32 C31 2.4(5) . . . . ?
C30 C31 C32 O4 -179.3(4) . . . . ?
C33 C31 C32 O4 55.0(6) . . . . ?
C30 C31 C32 N3 -2.1(5) . . . . ?
C33 C31 C32 N3 -127.8(4) . . . . ?
C30 C31 C33 C34 137.0(4) . . . . ?
C32 C31 C33 C34 -105.4(5) . . . . ?
C30 C31 C33 C35 -50.2(5) . . . . ?
C32 C31 C33 C35 67.4(5) . . . . ?
C42 N4 C34 C33 174.5(4) . . . . ?
C35 C33 C34 N4 -174.4(4) . . . . ?
C31 C33 C34 N4 -1.8(7) . . . . ?
C34 C33 C35 O5 154.5(4) . . . . ?
C31 C33 C35 O5 -18.7(6) . . . . ?
C34 C33 C35 C36 -26.1(6) . . . . ?
C31 C33 C35 C36 160.7(4) . . . . ?
O5 C35 C36 C41 131.8(5) . . . . ?
C33 C35 C36 C41 -47.6(6) . . . . ?
O5 C35 C36 C37 -43.4(7) . . . . ?
C33 C35 C36 C37 137.2(5) . . . . ?
C41 C36 C37 C38 2.9(8) . . . . ?
C35 C36 C37 C38 178.2(5) . . . . ?
C36 C37 C38 C39 -3.0(10) . . . . ?
C37 C38 C39 C40 1.4(11) . . . . ?
C38 C39 C40 C41 0.2(11) . . . . ?
C39 C40 C41 C36 -0.2(9) . . . . ?
C37 C36 C41 C40 -1.4(8) . . . . ?
C35 C36 C41 C40 -176.5(5) . . . . ?
C34 N4 C42 C47 17.4(6) . . . . ?
C34 N4 C42 C43 -161.0(4) . . . . ?
C47 C42 C43 C44 -0.9(6) . . . . ?
N4 C42 C43 C44 177.7(4) . . . . ?
C42 C43 C44 C45 0.2(7) . . . . ?
C48 O6 C45 C46 7.2(7) . . . . ?
C48 O6 C45 C44 -172.6(5) . . . . ?
C43 C44 C45 O6 -179.5(4) . . . . ?
C43 C44 C45 C46 0.7(7) . . . . ?
O6 C45 C46 C47 179.4(4) . . . . ?
C44 C45 C46 C47 -0.8(7) . . . . ?
C43 C42 C47 C46 0.7(7) . . . . ?
N4 C42 C47 C46 -177.7(4) . . . . ?
C45 C46 C47 C42 0.1(7) . . . . ?

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
N3 H3 O7 0.77(5) 2.30(5) 2.952(7) 143(5) .
N4 H4A O1 0.84(4) 2.11(5) 2.946(5) 173(4) 1_655
N2 H2A O4 0.83(4) 2.02(4) 2.831(5) 168(4) 1_455
C31 H31 O1 0.98 2.51 3.451(6) 160.3 1_655
C22 H22 O7 0.93 2.61 3.391(8) 141.4 .
C7 H7 O4 0.98 2.45 3.388(6) 159.1 1_455
C22 H22 O7 0.93 2.61 3.391(8) 141.4 .

_refine_diff_density_max         0.468
_refine_diff_density_min         -0.310
_refine_diff_density_rms         0.073

_shelxl_version_number           2013-4

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

data_mo_dm14733_0m
_database_code_depnum_ccdc_archive 'CCDC 1437093'
_audit_update_record             
;
2015-11-16 deposited with the CCDC.
2016-01-12 downloaded from the CCDC.
;
_audit_creation_date             2014-12-16
_audit_creation_method           
;
Olex2 1.2
(compiled 2014.07.22 svn.r2960 for OlexSys, GUI svn.r4862)
;
_shelxl_version_number           2014-3
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C24 H16 Cl2 N2 O2, C H Cl3'
_chemical_formula_sum            'C25 H17 Cl5 N2 O2'
_chemical_formula_weight         554.65
_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                   7.0166(5)
_cell_length_b                   13.2800(9)
_cell_length_c                   13.9998(10)
_cell_angle_alpha                66.5140(10)
_cell_angle_beta                 85.3090(10)
_cell_angle_gamma                89.3010(10)
_cell_volume                     1192.13(15)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    4397
_cell_measurement_temperature    130
_cell_measurement_theta_max      30.526
_cell_measurement_theta_min      2.731
_shelx_estimated_absorpt_T_max   0.894
_shelx_estimated_absorpt_T_min   0.808
_exptl_absorpt_coefficient_mu    0.636
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6543
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2008/1 (Bruker,2008) was used for absorption correction.
wR2(int) was 0.0729 before and 0.0297 after correction.
The Ratio of minimum to maximum transmission is 0.8770.
The λ/2 correction factor is 0.0015.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.545
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             564
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.18
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0187
_diffrn_reflns_av_unetI/netI     0.0346
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            12148
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.572
_diffrn_reflns_theta_min         1.672
_diffrn_ambient_temperature      130
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5734
_reflns_number_total             7236
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXS (Sheldrick, 2008)'
_refine_diff_density_max         1.570
_refine_diff_density_min         -1.663
_refine_diff_density_rms         0.088
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     308
_refine_ls_number_reflns         7236
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0681
_refine_ls_R_factor_gt           0.0537
_refine_ls_restrained_S_all      1.053
_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)+(0.0682P)²+1.0819P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1357
_refine_ls_wR_factor_ref         0.1467
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C25(H25)
2.b Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C7(H7), C13(H13), C14(H14), C15(H15), C16(H16), C17(H17), C19(H19),
 C20(H20), C22(H22), C23(H23)
2.d Idealised Me refined as rotating group:
 C24(H24A,H24B,H24C)
;
_atom_sites_solution_hydrogens   geom
_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 0.59133(8) -0.33808(4) 0.44211(4) 0.02908(13) Uani 1 1 d . . . . .
Cl2 Cl 0.64201(8) -0.29442(4) 0.04882(4) 0.02731(12) Uani 1 1 d . . . . .
O1 O 0.7407(3) -0.19310(12) 0.52515(12) 0.0310(4) Uani 1 1 d . . . . .
O2 O 0.8276(2) 0.04660(13) 0.83929(11) 0.0283(3) Uani 1 1 d . . . . .
N1 N 0.7364(2) -0.00527(13) 0.46903(12) 0.0167(3) Uani 1 1 d . . . . .
N2 N 0.7056(2) 0.04160(13) 0.12525(12) 0.0184(3) Uani 1 1 d . . . . .
C1 C 0.7236(3) -0.10271(15) 0.45644(14) 0.0182(3) Uani 1 1 d . . . . .
C2 C 0.6922(3) -0.07206(14) 0.34337(13) 0.0160(3) Uani 1 1 d . . . . .
C3 C 0.6770(3) -0.13468(14) 0.28105(14) 0.0167(3) Uani 1 1 d . . . . .
C4 C 0.6467(3) -0.24966(15) 0.31309(15) 0.0190(3) Uani 1 1 d . . . . .
C5 C 0.6432(3) -0.29748(15) 0.24238(16) 0.0209(4) Uani 1 1 d . . . . .
H5 H 0.6281 -0.3749 0.2662 0.025 Uiso 1 1 calc R . . . .
C6 C 0.6620(3) -0.23161(16) 0.13508(15) 0.0199(3) Uani 1 1 d . . . . .
C7 C 0.6840(3) -0.12059(16) 0.09803(15) 0.0199(3) Uani 1 1 d . . . . .
H7 H 0.6953 -0.0773 0.0249 0.024 Uiso 1 1 calc R . . . .
C8 C 0.6898(3) -0.07047(15) 0.17018(14) 0.0168(3) Uani 1 1 d . . . . .
C9 C 0.7034(3) 0.09627(15) 0.18572(14) 0.0169(3) Uani 1 1 d . . . . .
C10 C 0.6976(3) 0.04009(14) 0.29567(13) 0.0159(3) Uani 1 1 d . . . . .
C11 C 0.7185(3) 0.09009(14) 0.37247(13) 0.0167(3) Uani 1 1 d . . . . .
H11A H 0.8339 0.1385 0.3531 0.020 Uiso 1 1 calc R . . . .
H11B H 0.6047 0.1328 0.3781 0.020 Uiso 1 1 calc R . . . .
C12 C 0.7197(3) 0.21768(15) 0.13312(14) 0.0181(3) Uani 1 1 d . . . . .
C13 C 0.6037(3) 0.28558(16) 0.16614(15) 0.0208(4) Uani 1 1 d . . . . .
H13 H 0.5146 0.2544 0.2257 0.025 Uiso 1 1 calc R . . . .
C14 C 0.6183(3) 0.39877(16) 0.11213(16) 0.0239(4) Uani 1 1 d . . . . .
H14 H 0.5385 0.4449 0.1345 0.029 Uiso 1 1 calc R . . . .
C15 C 0.7489(3) 0.44450(16) 0.02571(16) 0.0254(4) Uani 1 1 d . . . . .
H15 H 0.7579 0.5220 -0.0113 0.030 Uiso 1 1 calc R . . . .
C16 C 0.8666(3) 0.37748(16) -0.00697(16) 0.0239(4) Uani 1 1 d . . . . .
H16 H 0.9568 0.4090 -0.0659 0.029 Uiso 1 1 calc R . . . .
C17 C 0.8521(3) 0.26403(16) 0.04680(14) 0.0204(4) Uani 1 1 d . . . . .
H17 H 0.9326 0.2181 0.0246 0.025 Uiso 1 1 calc R . . . .
C18 C 0.7659(3) 0.00744(15) 0.56245(14) 0.0170(3) Uani 1 1 d . . . . .
C19 C 0.7801(3) -0.08205(16) 0.65786(14) 0.0194(3) Uani 1 1 d . . . . .
H19 H 0.7757 -0.1547 0.6607 0.023 Uiso 1 1 calc R . . . .
C20 C 0.8005(3) -0.06541(17) 0.74795(15) 0.0223(4) Uani 1 1 d . . . . .
H20 H 0.8078 -0.1269 0.8124 0.027 Uiso 1 1 calc R . . . .
C21 C 0.8104(3) 0.04025(17) 0.74529(15) 0.0211(4) Uani 1 1 d . . . . .
C22 C 0.8021(3) 0.12969(16) 0.65072(15) 0.0211(4) Uani 1 1 d . . . . .
H22 H 0.8123 0.2022 0.6477 0.025 Uiso 1 1 calc R . . . .
C23 C 0.7790(3) 0.11302(16) 0.56052(15) 0.0199(3) Uani 1 1 d . . . . .
H23 H 0.7719 0.1747 0.4962 0.024 Uiso 1 1 calc R . . . .
C24 C 0.8286(3) 0.15357(19) 0.84037(17) 0.0285(4) Uani 1 1 d . . . . .
H24A H 0.9457 0.1937 0.8017 0.043 Uiso 1 1 calc GR . . . .
H24B H 0.8238 0.1471 0.9128 0.043 Uiso 1 1 calc GR . . . .
H24C H 0.7170 0.1934 0.8074 0.043 Uiso 1 1 calc GR . . . .
Cl3 Cl 1.21817(15) 0.53369(7) 0.30201(7) 0.0657(3) Uani 1 1 d . . . . .
Cl4 Cl 0.87009(17) 0.42830(10) 0.41907(11) 0.1007(5) Uani 1 1 d . . . . .
Cl5 Cl 1.03338(17) 0.37163(6) 0.25262(7) 0.0746(3) Uani 1 1 d . . . . .
C25 C 1.0806(4) 0.41255(19) 0.3538(2) 0.0354(5) Uani 1 1 d . . . . .
H25 H 1.1557 0.3540 0.4047 0.042 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 C4 1.7315(19) . ?
Cl2 C6 1.7341(19) . ?
O1 C1 1.215(2) . ?
O2 C21 1.367(2) . ?
O2 C24 1.427(3) . ?
N1 C1 1.379(2) . ?
N1 C11 1.451(2) . ?
N1 C18 1.415(2) . ?
N2 C8 1.367(2) . ?
N2 C9 1.316(2) . ?
C1 C2 1.504(2) . ?
C2 C3 1.435(2) . ?
C2 C10 1.367(2) . ?
C3 C4 1.423(2) . ?
C3 C8 1.438(2) . ?
C4 C5 1.375(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.401(3) . ?
C6 C7 1.360(3) . ?
C7 H7 0.9500 . ?
C7 C8 1.417(2) . ?
C9 C10 1.415(2) . ?
C9 C12 1.483(2) . ?
C10 C11 1.489(2) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.394(3) . ?
C12 C17 1.392(3) . ?
C13 H13 0.9500 . ?
C13 C14 1.388(3) . ?
C14 H14 0.9500 . ?
C14 C15 1.385(3) . ?
C15 H15 0.9500 . ?
C15 C16 1.389(3) . ?
C16 H16 0.9500 . ?
C16 C17 1.391(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.400(3) . ?
C18 C23 1.396(3) . ?
C19 H19 0.9500 . ?
C19 C20 1.383(3) . ?
C20 H20 0.9500 . ?
C20 C21 1.391(3) . ?
C21 C22 1.387(3) . ?
C22 H22 0.9500 . ?
C22 C23 1.388(3) . ?
C23 H23 0.9500 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
Cl3 C25 1.743(2) . ?
Cl4 C25 1.728(3) . ?
Cl5 C25 1.762(3) . ?
C25 H25 1.0000 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C21 O2 C24 117.12(17) . . ?
C1 N1 C11 112.59(14) . . ?
C1 N1 C18 126.84(15) . . ?
C18 N1 C11 120.56(15) . . ?
C9 N2 C8 119.12(16) . . ?
O1 C1 N1 124.63(17) . . ?
O1 C1 C2 129.16(17) . . ?
N1 C1 C2 106.18(15) . . ?
C3 C2 C1 133.31(16) . . ?
C10 C2 C1 107.28(15) . . ?
C10 C2 C3 119.13(16) . . ?
C2 C3 C8 114.58(15) . . ?
C4 C3 C2 129.50(17) . . ?
C4 C3 C8 115.90(16) . . ?
C3 C4 Cl1 122.99(14) . . ?
C5 C4 Cl1 114.72(14) . . ?
C5 C4 C3 122.06(17) . . ?
C4 C5 H5 120.1 . . ?
C4 C5 C6 119.72(17) . . ?
C6 C5 H5 120.1 . . ?
C5 C6 Cl2 118.14(14) . . ?
C7 C6 Cl2 119.90(15) . . ?
C7 C6 C5 121.85(17) . . ?
C6 C7 H7 120.5 . . ?
C6 C7 C8 118.94(17) . . ?
C8 C7 H7 120.5 . . ?
N2 C8 C3 124.19(16) . . ?
N2 C8 C7 114.41(16) . . ?
C7 C8 C3 121.39(16) . . ?
N2 C9 C10 120.70(16) . . ?
N2 C9 C12 116.99(16) . . ?
C10 C9 C12 122.19(16) . . ?
C2 C10 C9 121.90(16) . . ?
C2 C10 C11 111.20(15) . . ?
C9 C10 C11 126.55(16) . . ?
N1 C11 C10 102.62(14) . . ?
N1 C11 H11A 111.2 . . ?
N1 C11 H11B 111.2 . . ?
C10 C11 H11A 111.2 . . ?
C10 C11 H11B 111.2 . . ?
H11A C11 H11B 109.2 . . ?
C13 C12 C9 121.86(17) . . ?
C17 C12 C9 118.44(17) . . ?
C17 C12 C13 119.68(17) . . ?
C12 C13 H13 120.0 . . ?
C14 C13 C12 120.04(18) . . ?
C14 C13 H13 120.0 . . ?
C13 C14 H14 120.0 . . ?
C15 C14 C13 120.09(19) . . ?
C15 C14 H14 120.0 . . ?
C14 C15 H15 119.9 . . ?
C14 C15 C16 120.23(18) . . ?
C16 C15 H15 119.9 . . ?
C15 C16 H16 120.1 . . ?
C15 C16 C17 119.83(19) . . ?
C17 C16 H16 120.1 . . ?
C12 C17 H17 119.9 . . ?
C16 C17 C12 120.13(18) . . ?
C16 C17 H17 119.9 . . ?
C19 C18 N1 122.61(16) . . ?
C23 C18 N1 119.16(16) . . ?
C23 C18 C19 118.22(17) . . ?
C18 C19 H19 119.8 . . ?
C20 C19 C18 120.44(18) . . ?
C20 C19 H19 119.8 . . ?
C19 C20 H20 119.6 . . ?
C19 C20 C21 120.78(18) . . ?
C21 C20 H20 119.6 . . ?
O2 C21 C20 115.60(18) . . ?
O2 C21 C22 125.03(18) . . ?
C22 C21 C20 119.37(17) . . ?
C21 C22 H22 120.1 . . ?
C21 C22 C23 119.86(18) . . ?
C23 C22 H22 120.1 . . ?
C18 C23 H23 119.4 . . ?
C22 C23 C18 121.30(18) . . ?
C22 C23 H23 119.4 . . ?
O2 C24 H24A 109.5 . . ?
O2 C24 H24B 109.5 . . ?
O2 C24 H24C 109.5 . . ?
H24A C24 H24B 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
Cl3 C25 Cl5 109.46(14) . . ?
Cl3 C25 H25 108.4 . . ?
Cl4 C25 Cl3 111.28(15) . . ?
Cl4 C25 Cl5 110.77(16) . . ?
Cl4 C25 H25 108.4 . . ?
Cl5 C25 H25 108.4 . . ?

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 C4 C5 C6 172.04(15) . . . . ?
Cl2 C6 C7 C8 176.68(14) . . . . ?
O1 C1 C2 C3 -1.5(4) . . . . ?
O1 C1 C2 C10 -175.2(2) . . . . ?
O2 C21 C22 C23 -178.17(18) . . . . ?
N1 C1 C2 C3 176.47(19) . . . . ?
N1 C1 C2 C10 2.8(2) . . . . ?
N1 C18 C19 C20 -177.12(17) . . . . ?
N1 C18 C23 C22 178.04(17) . . . . ?
N2 C9 C10 C2 -0.6(3) . . . . ?
N2 C9 C10 C11 171.95(17) . . . . ?
N2 C9 C12 C13 135.67(19) . . . . ?
N2 C9 C12 C17 -42.7(2) . . . . ?
C1 N1 C11 C10 -1.45(19) . . . . ?
C1 N1 C18 C19 -2.1(3) . . . . ?
C1 N1 C18 C23 178.75(18) . . . . ?
C1 C2 C3 C4 15.1(3) . . . . ?
C1 C2 C3 C8 -166.60(18) . . . . ?
C1 C2 C10 C9 169.77(16) . . . . ?
C1 C2 C10 C11 -3.9(2) . . . . ?
C2 C3 C4 Cl1 8.4(3) . . . . ?
C2 C3 C4 C5 -177.35(19) . . . . ?
C2 C3 C8 N2 -3.1(3) . . . . ?
C2 C3 C8 C7 177.78(16) . . . . ?
C2 C10 C11 N1 3.34(19) . . . . ?
C3 C2 C10 C9 -4.9(3) . . . . ?
C3 C2 C10 C11 -178.56(16) . . . . ?
C3 C4 C5 C6 -2.7(3) . . . . ?
C4 C3 C8 N2 175.41(17) . . . . ?
C4 C3 C8 C7 -3.7(3) . . . . ?
C4 C5 C6 Cl2 -176.10(15) . . . . ?
C4 C5 C6 C7 0.1(3) . . . . ?
C5 C6 C7 C8 0.6(3) . . . . ?
C6 C7 C8 N2 -177.83(17) . . . . ?
C6 C7 C8 C3 1.3(3) . . . . ?
C8 N2 C9 C10 4.2(3) . . . . ?
C8 N2 C9 C12 -179.61(16) . . . . ?
C8 C3 C4 Cl1 -169.93(14) . . . . ?
C8 C3 C4 C5 4.4(3) . . . . ?
C9 N2 C8 C3 -2.2(3) . . . . ?
C9 N2 C8 C7 176.95(17) . . . . ?
C9 C10 C11 N1 -169.93(17) . . . . ?
C9 C12 C13 C14 -177.39(18) . . . . ?
C9 C12 C17 C16 177.60(18) . . . . ?
C10 C2 C3 C4 -171.86(18) . . . . ?
C10 C2 C3 C8 6.4(2) . . . . ?
C10 C9 C12 C13 -48.2(3) . . . . ?
C10 C9 C12 C17 133.43(19) . . . . ?
C11 N1 C1 O1 177.40(19) . . . . ?
C11 N1 C1 C2 -0.7(2) . . . . ?
C11 N1 C18 C19 178.67(17) . . . . ?
C11 N1 C18 C23 -0.4(2) . . . . ?
C12 C9 C10 C2 -176.67(17) . . . . ?
C12 C9 C10 C11 -4.1(3) . . . . ?
C12 C13 C14 C15 -0.4(3) . . . . ?
C13 C12 C17 C16 -0.8(3) . . . . ?
C13 C14 C15 C16 -0.4(3) . . . . ?
C14 C15 C16 C17 0.5(3) . . . . ?
C15 C16 C17 C12 0.1(3) . . . . ?
C17 C12 C13 C14 1.0(3) . . . . ?
C18 N1 C1 O1 -1.8(3) . . . . ?
C18 N1 C1 C2 -179.97(16) . . . . ?
C18 N1 C11 C10 177.85(15) . . . . ?
C18 C19 C20 C21 -1.1(3) . . . . ?
C19 C18 C23 C22 -1.1(3) . . . . ?
C19 C20 C21 O2 179.07(18) . . . . ?
C19 C20 C21 C22 -0.8(3) . . . . ?
C20 C21 C22 C23 1.7(3) . . . . ?
C21 C22 C23 C18 -0.7(3) . . . . ?
C23 C18 C19 C20 2.0(3) . . . . ?
C24 O2 C21 C20 -176.96(18) . . . . ?
C24 O2 C21 C22 2.9(3) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
