# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_4310
_database_code_depnum_ccdc_archive 'CCDC 990981'
_audit_update_record             
;
2014-03-11 deposited with the CCDC.
2015-05-12 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C39 H42 Cl2 N O6 P'
_chemical_formula_weight         722.61

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'
P P 0.2955 0.4335 '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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21'
_symmetry_Hall_group_name_H-M    'P 2yb'
_symmetry_Int_Tables_number      4

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

_cell_length_a                   9.921(3)
_cell_length_b                   16.320(4)
_cell_length_c                   11.549(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.356(5)
_cell_angle_gamma                90.00
_cell_volume                     1854.5(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    93(2)
_cell_measurement_reflns_used    1473
_cell_measurement_theta_min      25.4
_cell_measurement_theta_max      68.1

_exptl_crystal_description       Prism
_exptl_crystal_colour            Colorless
_exptl_crystal_size_max          0.08
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.01
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             760
_exptl_absorpt_coefficient_mu    2.361
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8336
_exptl_absorpt_correction_T_max  0.9768
_exptl_absorpt_process_details   'REQAB(Rigaku, 1998)'

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      93(2)
_diffrn_radiation_wavelength     1.54187
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku XtaLAB P200'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean 5.8140
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            14750
_diffrn_reflns_av_R_equivalents  0.0536
_diffrn_reflns_av_sigmaI/netI    0.0628
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         6.66
_diffrn_reflns_theta_max         68.32
_reflns_number_total             6264
_reflns_number_gt                5411
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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)+(0.0613P)²+0.8114P] 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'
_chemical_absolute_configuration rm
_refine_ls_abs_structure_Flack   -0.024(19)
_refine_ls_number_reflns         6264
_refine_ls_number_parameters     446
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0629
_refine_ls_R_factor_gt           0.0518
_refine_ls_wR_factor_ref         0.1357
_refine_ls_wR_factor_gt          0.1233
_refine_ls_goodness_of_fit_ref   1.059
_refine_ls_restrained_S_all      1.058
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.9908(3) 0.34449(19) 1.0654(2) 0.0259(6) Uani 1 1 d . . .
H1 H 1.0270 0.2929 1.0548 0.031 Uiso 1 1 calc R . .
C1 C 0.8426(4) 0.3342(3) 1.0730(3) 0.0301(8) Uani 1 1 d . . .
H1A H 0.8027 0.3878 1.0899 0.036 Uiso 1 1 calc R . .
H1B H 0.8302 0.2964 1.1379 0.036 Uiso 1 1 calc R . .
C2 C 0.7696(4) 0.3004(2) 0.9602(3) 0.0280(8) Uani 1 1 d . . .
H2 H 0.6716 0.2945 0.9670 0.034 Uiso 1 1 calc R . .
H2A H 0.8062 0.2455 0.9453 0.034 Uiso 1 1 calc R . .
C3 C 0.7880(4) 0.3579(2) 0.8575(3) 0.0266(8) Uani 1 1 d . . .
H3 H 0.7519 0.4132 0.8745 0.032 Uiso 1 1 calc R . .
C4 C 0.9396(4) 0.3660(2) 0.8474(3) 0.0307(8) Uani 1 1 d . . .
H4 H 0.9760 0.3109 0.8300 0.037 Uiso 1 1 calc R . .
C5 C 1.0138(4) 0.3962(2) 0.9628(3) 0.0292(8) Uani 1 1 d . . .
H5 H 1.1125 0.3978 0.9569 0.035 Uiso 1 1 calc R . .
H5A H 0.9841 0.4529 0.9764 0.035 Uiso 1 1 calc R . .
C6 C 0.7064(4) 0.3251(2) 0.7490(3) 0.0294(8) Uani 1 1 d . . .
O1 O 0.7499(3) 0.27837(18) 0.6806(2) 0.0389(7) Uani 1 1 d . . .
O2 O 0.5777(2) 0.35170(17) 0.7404(2) 0.0300(6) Uani 1 1 d . . .
C7 C 0.4709(4) 0.3217(3) 0.6478(3) 0.0322(9) Uani 1 1 d . . .
C8 C 0.4518(5) 0.2302(3) 0.6643(4) 0.0504(12) Uani 1 1 d . . .
H8 H 0.5302 0.2007 0.6413 0.076 Uiso 1 1 calc R . .
H8A H 0.3689 0.2121 0.6157 0.076 Uiso 1 1 calc R . .
H8B H 0.4440 0.2189 0.7465 0.076 Uiso 1 1 calc R . .
C9 C 0.3453(4) 0.3680(3) 0.6722(4) 0.0427(11) Uani 1 1 d . . .
H9 H 0.3191 0.3501 0.7472 0.064 Uiso 1 1 calc R . .
H9A H 0.2708 0.3569 0.6099 0.064 Uiso 1 1 calc R . .
H9B H 0.3647 0.4269 0.6752 0.064 Uiso 1 1 calc R . .
C10 C 0.5069(5) 0.3436(4) 0.5294(3) 0.0559(14) Uani 1 1 d . . .
H10 H 0.5264 0.4024 0.5268 0.084 Uiso 1 1 calc R . .
H10A H 0.4306 0.3303 0.4699 0.084 Uiso 1 1 calc R . .
H10B H 0.5874 0.3125 0.5143 0.084 Uiso 1 1 calc R . .
C11 C 0.9673(4) 0.4255(3) 0.7509(3) 0.0366(9) Uani 1 1 d . . .
H11 H 0.9267 0.4041 0.6751 0.055 Uiso 1 1 calc R . .
H11A H 1.0656 0.4315 0.7511 0.055 Uiso 1 1 calc R . .
H11B H 0.9273 0.4790 0.7646 0.055 Uiso 1 1 calc R . .
C12 C 1.0662(4) 0.3806(2) 1.1750(3) 0.0325(9) Uani 1 1 d . . .
H12 H 1.0320 0.4368 1.1850 0.039 Uiso 1 1 calc R . .
H12A H 1.1637 0.3848 1.1654 0.039 Uiso 1 1 calc R . .
C13 C 1.0533(4) 0.3324(2) 1.2844(3) 0.0314(9) Uani 1 1 d . . .
C14 C 0.9513(4) 0.3493(3) 1.3533(4) 0.0449(11) Uani 1 1 d . . .
H14 H 0.8875 0.3915 1.3301 0.054 Uiso 1 1 calc R . .
C15 C 0.9410(5) 0.3063(3) 1.4547(4) 0.0493(12) Uani 1 1 d . . .
H15 H 0.8696 0.3182 1.4996 0.059 Uiso 1 1 calc R . .
C16 C 1.0338(5) 0.2461(3) 1.4908(3) 0.0437(11) Uani 1 1 d . . .
H16 H 1.0281 0.2171 1.5614 0.052 Uiso 1 1 calc R . .
C17 C 1.1363(4) 0.2280(3) 1.4230(3) 0.0397(10) Uani 1 1 d . . .
H17 H 1.2009 0.1866 1.4476 0.048 Uiso 1 1 calc R . .
C18 C 1.1449(4) 0.2700(3) 1.3202(3) 0.0324(9) Uani 1 1 d . . .
H18 H 1.2138 0.2561 1.2736 0.039 Uiso 1 1 calc R . .
P1 P 0.13613(8) 0.12759(6) 0.97478(7) 0.0250(2) Uani 1 1 d . . .
O3 O 0.1216(3) 0.20880(16) 1.0293(2) 0.0317(6) Uani 1 1 d . . .
O4 O 0.0208(3) 0.08592(17) 0.9078(2) 0.0319(6) Uani 1 1 d . . .
O5 O 0.2625(2) 0.13838(15) 0.89981(19) 0.0242(5) Uani 1 1 d . . .
O6 O 0.1987(2) 0.06230(15) 1.0746(2) 0.0251(5) Uani 1 1 d . . .
C19 C 0.3284(3) 0.0670(2) 0.8706(3) 0.0232(7) Uani 1 1 d . . .
C20 C 0.3015(4) 0.0370(2) 0.7565(3) 0.0282(8) Uani 1 1 d . . .
H20 H 0.2429 0.0663 0.6994 0.034 Uiso 1 1 calc R . .
C21 C 0.3599(4) -0.0343(2) 0.7278(3) 0.0283(8) Uani 1 1 d . . .
H21 H 0.3436 -0.0540 0.6499 0.034 Uiso 1 1 calc R . .
C22 C 0.4445(4) -0.0796(2) 0.8128(3) 0.0240(7) Uani 1 1 d . . .
C23 C 0.4946(4) -0.1590(2) 0.7890(3) 0.0290(8) Uani 1 1 d . . .
H23 H 0.4741 -0.1813 0.7128 0.035 Uiso 1 1 calc R . .
C24 C 0.5710(4) -0.2035(2) 0.8727(3) 0.0301(8) Uani 1 1 d . . .
H24 H 0.6022 -0.2566 0.8553 0.036 Uiso 1 1 calc R . .
C25 C 0.6034(4) -0.1705(2) 0.9854(3) 0.0282(8) Uani 1 1 d . . .
H25 H 0.6586 -0.2010 1.0434 0.034 Uiso 1 1 calc R . .
C26 C 0.5562(3) -0.0948(2) 1.0124(3) 0.0247(7) Uani 1 1 d . . .
H26 H 0.5774 -0.0739 1.0894 0.030 Uiso 1 1 calc R . .
C27 C 0.4766(3) -0.0476(2) 0.9269(3) 0.0222(7) Uani 1 1 d . . .
C28 C 0.4184(3) 0.0296(2) 0.9555(3) 0.0199(7) Uani 1 1 d . . .
C29 C 0.3280(3) 0.0755(2) 1.1338(3) 0.0236(7) Uani 1 1 d . . .
C30 C 0.3394(4) 0.0972(2) 1.2519(3) 0.0265(8) Uani 1 1 d . . .
H30 H 0.2604 0.1011 1.2903 0.032 Uiso 1 1 calc R . .
C31 C 0.4647(4) 0.1126(2) 1.3119(3) 0.0300(8) Uani 1 1 d . . .
H31 H 0.4731 0.1257 1.3926 0.036 Uiso 1 1 calc R . .
C32 C 0.5831(4) 0.1091(2) 1.2535(3) 0.0275(8) Uani 1 1 d . . .
C33 C 0.7133(4) 0.1304(3) 1.3107(3) 0.0351(8) Uani 1 1 d . . .
H33 H 0.7229 0.1458 1.3906 0.042 Uiso 1 1 calc R . .
C34 C 0.8258(4) 0.1290(3) 1.2528(3) 0.0363(9) Uani 1 1 d . . .
H34 H 0.9123 0.1437 1.2924 0.044 Uiso 1 1 calc R . .
C35 C 0.8126(4) 0.1058(2) 1.1346(3) 0.0319(9) Uani 1 1 d . . .
H35 H 0.8904 0.1054 1.0945 0.038 Uiso 1 1 calc R . .
C36 C 0.6889(4) 0.0839(2) 1.0767(3) 0.0262(7) Uani 1 1 d . . .
H36 H 0.6819 0.0684 0.9969 0.031 Uiso 1 1 calc R . .
C37 C 0.5712(3) 0.0840(2) 1.1343(3) 0.0237(7) Uani 1 1 d . . .
C38 C 0.4385(3) 0.0633(2) 1.0755(3) 0.0224(7) Uani 1 1 d . . .
Cl1 Cl 0.92138(15) 0.03838(9) 0.56549(11) 0.0677(4) Uani 1 1 d . . .
Cl2 Cl 0.68440(14) 0.03309(10) 0.69104(15) 0.0792(5) Uani 1 1 d . . .
C39 C 0.8327(5) 0.0878(3) 0.6674(4) 0.0516(12) Uani 1 1 d . . .
H39 H 0.8069 0.1436 0.6389 0.062 Uiso 1 1 calc R . .
H39A H 0.8928 0.0933 0.7423 0.062 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
N1 C1 1.494(4) . ?
N1 C5 1.496(5) . ?
N1 C12 1.506(4) . ?
N1 H1 0.9300 . ?
C1 C2 1.511(5) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.541(5) . ?
C2 H2 0.9900 . ?
C2 H2A 0.9900 . ?
C3 C6 1.501(5) . ?
C3 C4 1.529(5) . ?
C3 H3 1.0000 . ?
C4 C5 1.519(5) . ?
C4 C11 1.529(5) . ?
C4 H4 1.0000 . ?
C5 H5 0.9900 . ?
C5 H5A 0.9900 . ?
C6 O1 1.216(5) . ?
C6 O2 1.340(4) . ?
O2 C7 1.489(4) . ?
C7 C10 1.500(6) . ?
C7 C9 1.514(6) . ?
C7 C8 1.519(6) . ?
C8 H8 0.9800 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C9 H9 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C10 H10 0.9800 . ?
C10 H10A 0.9800 . ?
C10 H10B 0.9800 . ?
C11 H11 0.9800 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C12 C13 1.507(6) . ?
C12 H12 0.9900 . ?
C12 H12A 0.9900 . ?
C13 C18 1.392(5) . ?
C13 C14 1.393(6) . ?
C14 C15 1.381(7) . ?
C14 H14 0.9500 . ?
C15 C16 1.374(7) . ?
C15 H15 0.9500 . ?
C16 C17 1.392(6) . ?
C16 H16 0.9500 . ?
C17 C18 1.383(6) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
P1 O4 1.464(3) . ?
P1 O3 1.482(3) . ?
P1 O5 1.622(2) . ?
P1 O6 1.633(2) . ?
O5 C19 1.398(4) . ?
O6 C29 1.390(4) . ?
C19 C28 1.381(4) . ?
C19 C20 1.399(5) . ?
C20 C21 1.360(6) . ?
C20 H20 0.9500 . ?
C21 C22 1.415(5) . ?
C21 H21 0.9500 . ?
C22 C27 1.416(5) . ?
C22 C23 1.427(5) . ?
C23 C24 1.360(5) . ?
C23 H23 0.9500 . ?
C24 C25 1.407(5) . ?
C24 H24 0.9500 . ?
C25 C26 1.372(5) . ?
C25 H25 0.9500 . ?
C26 C27 1.411(5) . ?
C26 H26 0.9500 . ?
C27 C28 1.443(5) . ?
C28 C38 1.480(5) . ?
C29 C38 1.372(5) . ?
C29 C30 1.400(5) . ?
C30 C31 1.367(5) . ?
C30 H30 0.9500 . ?
C31 C32 1.428(5) . ?
C31 H31 0.9500 . ?
C32 C33 1.416(5) . ?
C32 C37 1.427(5) . ?
C33 C34 1.373(6) . ?
C33 H33 0.9500 . ?
C34 C35 1.406(5) . ?
C34 H34 0.9500 . ?
C35 C36 1.368(5) . ?
C35 H35 0.9500 . ?
C36 C37 1.416(5) . ?
C36 H36 0.9500 . ?
C37 C38 1.442(5) . ?
Cl1 C39 1.754(5) . ?
Cl2 C39 1.771(5) . ?
C39 H39 0.9900 . ?
C39 H39A 0.9900 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 N1 C5 111.2(3) . . ?
C1 N1 C12 112.4(3) . . ?
C5 N1 C12 109.6(3) . . ?
C1 N1 H1 107.8 . . ?
C5 N1 H1 107.8 . . ?
C12 N1 H1 107.8 . . ?
N1 C1 C2 110.9(3) . . ?
N1 C1 H1A 109.5 . . ?
C2 C1 H1A 109.5 . . ?
N1 C1 H1B 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 108.0 . . ?
C1 C2 C3 110.5(3) . . ?
C1 C2 H2 109.5 . . ?
C3 C2 H2 109.5 . . ?
C1 C2 H2A 109.5 . . ?
C3 C2 H2A 109.5 . . ?
H2 C2 H2A 108.1 . . ?
C6 C3 C4 113.5(3) . . ?
C6 C3 C2 108.8(3) . . ?
C4 C3 C2 109.0(3) . . ?
C6 C3 H3 108.5 . . ?
C4 C3 H3 108.5 . . ?
C2 C3 H3 108.5 . . ?
C5 C4 C3 109.4(3) . . ?
C5 C4 C11 108.8(3) . . ?
C3 C4 C11 112.4(3) . . ?
C5 C4 H4 108.7 . . ?
C3 C4 H4 108.7 . . ?
C11 C4 H4 108.7 . . ?
N1 C5 C4 114.0(3) . . ?
N1 C5 H5 108.8 . . ?
C4 C5 H5 108.8 . . ?
N1 C5 H5A 108.8 . . ?
C4 C5 H5A 108.8 . . ?
H5 C5 H5A 107.7 . . ?
O1 C6 O2 124.7(3) . . ?
O1 C6 C3 124.6(3) . . ?
O2 C6 C3 110.7(3) . . ?
C6 O2 C7 122.0(3) . . ?
O2 C7 C10 110.2(3) . . ?
O2 C7 C9 103.2(3) . . ?
C10 C7 C9 110.4(4) . . ?
O2 C7 C8 108.8(3) . . ?
C10 C7 C8 113.4(4) . . ?
C9 C7 C8 110.4(4) . . ?
C7 C8 H8 109.5 . . ?
C7 C8 H8A 109.5 . . ?
H8 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C9 H9 109.5 . . ?
C7 C9 H9A 109.5 . . ?
H9 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
H9 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C7 C10 H10 109.5 . . ?
C7 C10 H10A 109.5 . . ?
H10 C10 H10A 109.5 . . ?
C7 C10 H10B 109.5 . . ?
H10 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C4 C11 H11 109.5 . . ?
C4 C11 H11A 109.5 . . ?
H11 C11 H11A 109.5 . . ?
C4 C11 H11B 109.5 . . ?
H11 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
N1 C12 C13 114.5(3) . . ?
N1 C12 H12 108.6 . . ?
C13 C12 H12 108.6 . . ?
N1 C12 H12A 108.6 . . ?
C13 C12 H12A 108.6 . . ?
H12 C12 H12A 107.6 . . ?
C18 C13 C14 118.0(4) . . ?
C18 C13 C12 120.6(3) . . ?
C14 C13 C12 121.4(4) . . ?
C15 C14 C13 121.5(4) . . ?
C15 C14 H14 119.3 . . ?
C13 C14 H14 119.3 . . ?
C16 C15 C14 120.1(4) . . ?
C16 C15 H15 119.9 . . ?
C14 C15 H15 119.9 . . ?
C15 C16 C17 119.3(4) . . ?
C15 C16 H16 120.3 . . ?
C17 C16 H16 120.3 . . ?
C18 C17 C16 120.5(4) . . ?
C18 C17 H17 119.7 . . ?
C16 C17 H17 119.7 . . ?
C17 C18 C13 120.5(4) . . ?
C17 C18 H18 119.7 . . ?
C13 C18 H18 119.7 . . ?
O4 P1 O3 121.88(16) . . ?
O4 P1 O5 111.93(14) . . ?
O3 P1 O5 104.69(14) . . ?
O4 P1 O6 105.71(14) . . ?
O3 P1 O6 109.39(14) . . ?
O5 P1 O6 101.41(12) . . ?
C19 O5 P1 117.1(2) . . ?
C29 O6 P1 119.3(2) . . ?
C28 C19 O5 118.4(3) . . ?
C28 C19 C20 122.9(3) . . ?
O5 C19 C20 118.7(3) . . ?
C21 C20 C19 119.5(3) . . ?
C21 C20 H20 120.2 . . ?
C19 C20 H20 120.2 . . ?
C20 C21 C22 120.8(3) . . ?
C20 C21 H21 119.6 . . ?
C22 C21 H21 119.6 . . ?
C21 C22 C27 119.7(3) . . ?
C21 C22 C23 122.1(3) . . ?
C27 C22 C23 118.2(3) . . ?
C24 C23 C22 121.6(3) . . ?
C24 C23 H23 119.2 . . ?
C22 C23 H23 119.2 . . ?
C23 C24 C25 119.6(3) . . ?
C23 C24 H24 120.2 . . ?
C25 C24 H24 120.2 . . ?
C26 C25 C24 120.8(3) . . ?
C26 C25 H25 119.6 . . ?
C24 C25 H25 119.6 . . ?
C25 C26 C27 120.6(3) . . ?
C25 C26 H26 119.7 . . ?
C27 C26 H26 119.7 . . ?
C26 C27 C22 119.3(3) . . ?
C26 C27 C28 121.4(3) . . ?
C22 C27 C28 119.1(3) . . ?
C19 C28 C27 117.7(3) . . ?
C19 C28 C38 119.9(3) . . ?
C27 C28 C38 121.9(3) . . ?
C38 C29 O6 118.8(3) . . ?
C38 C29 C30 123.0(3) . . ?
O6 C29 C30 118.2(3) . . ?
C31 C30 C29 119.7(3) . . ?
C31 C30 H30 120.2 . . ?
C29 C30 H30 120.2 . . ?
C30 C31 C32 120.2(3) . . ?
C30 C31 H31 119.9 . . ?
C32 C31 H31 119.9 . . ?
C33 C32 C37 118.6(3) . . ?
C33 C32 C31 121.7(3) . . ?
C37 C32 C31 119.7(3) . . ?
C34 C33 C32 121.2(3) . . ?
C34 C33 H33 119.4 . . ?
C32 C33 H33 119.4 . . ?
C33 C34 C35 119.8(3) . . ?
C33 C34 H34 120.1 . . ?
C35 C34 H34 120.1 . . ?
C36 C35 C34 120.8(4) . . ?
C36 C35 H35 119.6 . . ?
C34 C35 H35 119.6 . . ?
C35 C36 C37 120.8(3) . . ?
C35 C36 H36 119.6 . . ?
C37 C36 H36 119.6 . . ?
C36 C37 C32 118.8(3) . . ?
C36 C37 C38 122.5(3) . . ?
C32 C37 C38 118.7(3) . . ?
C29 C38 C37 118.3(3) . . ?
C29 C38 C28 119.5(3) . . ?
C37 C38 C28 122.2(3) . . ?
Cl1 C39 Cl2 111.7(3) . . ?
Cl1 C39 H39 109.3 . . ?
Cl2 C39 H39 109.3 . . ?
Cl1 C39 H39A 109.3 . . ?
Cl2 C39 H39A 109.3 . . ?
H39 C39 H39A 107.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C5 N1 C1 C2 54.8(4) . . . . ?
C12 N1 C1 C2 178.2(3) . . . . ?
N1 C1 C2 C3 -58.8(4) . . . . ?
C1 C2 C3 C6 -176.2(3) . . . . ?
C1 C2 C3 C4 59.6(4) . . . . ?
C6 C3 C4 C5 -177.7(3) . . . . ?
C2 C3 C4 C5 -56.3(4) . . . . ?
C6 C3 C4 C11 61.4(4) . . . . ?
C2 C3 C4 C11 -177.3(3) . . . . ?
C1 N1 C5 C4 -53.9(4) . . . . ?
C12 N1 C5 C4 -178.8(3) . . . . ?
C3 C4 C5 N1 54.8(4) . . . . ?
C11 C4 C5 N1 178.0(3) . . . . ?
C4 C3 C6 O1 29.9(5) . . . . ?
C2 C3 C6 O1 -91.7(4) . . . . ?
C4 C3 C6 O2 -152.7(3) . . . . ?
C2 C3 C6 O2 85.8(4) . . . . ?
O1 C6 O2 C7 3.9(6) . . . . ?
C3 C6 O2 C7 -173.5(3) . . . . ?
C6 O2 C7 C10 -61.9(5) . . . . ?
C6 O2 C7 C9 -179.8(3) . . . . ?
C6 O2 C7 C8 62.9(4) . . . . ?
C1 N1 C12 C13 57.2(4) . . . . ?
C5 N1 C12 C13 -178.6(3) . . . . ?
N1 C12 C13 C18 89.1(4) . . . . ?
N1 C12 C13 C14 -91.7(4) . . . . ?
C18 C13 C14 C15 0.4(6) . . . . ?
C12 C13 C14 C15 -178.8(4) . . . . ?
C13 C14 C15 C16 1.1(7) . . . . ?
C14 C15 C16 C17 -1.3(7) . . . . ?
C15 C16 C17 C18 -0.1(6) . . . . ?
C16 C17 C18 C13 1.7(6) . . . . ?
C14 C13 C18 C17 -1.9(6) . . . . ?
C12 C13 C18 C17 177.3(3) . . . . ?
O4 P1 O5 C19 -66.7(3) . . . . ?
O3 P1 O5 C19 159.4(2) . . . . ?
O6 P1 O5 C19 45.6(2) . . . . ?
O4 P1 O6 C29 164.3(2) . . . . ?
O3 P1 O6 C29 -62.8(3) . . . . ?
O5 P1 O6 C29 47.4(3) . . . . ?
P1 O5 C19 C28 -77.4(3) . . . . ?
P1 O5 C19 C20 103.3(3) . . . . ?
C28 C19 C20 C21 3.7(5) . . . . ?
O5 C19 C20 C21 -177.1(3) . . . . ?
C19 C20 C21 C22 1.6(5) . . . . ?
C20 C21 C22 C27 -4.4(5) . . . . ?
C20 C21 C22 C23 172.7(4) . . . . ?
C21 C22 C23 C24 -177.1(3) . . . . ?
C27 C22 C23 C24 0.1(5) . . . . ?
C22 C23 C24 C25 -0.9(5) . . . . ?
C23 C24 C25 C26 1.5(5) . . . . ?
C24 C25 C26 C27 -1.4(5) . . . . ?
C25 C26 C27 C22 0.6(5) . . . . ?
C25 C26 C27 C28 175.7(3) . . . . ?
C21 C22 C27 C26 177.3(3) . . . . ?
C23 C22 C27 C26 0.1(5) . . . . ?
C21 C22 C27 C28 2.0(5) . . . . ?
C23 C22 C27 C28 -175.2(3) . . . . ?
O5 C19 C28 C27 174.8(3) . . . . ?
C20 C19 C28 C27 -5.9(5) . . . . ?
O5 C19 C28 C38 2.7(5) . . . . ?
C20 C19 C28 C38 -178.0(3) . . . . ?
C26 C27 C28 C19 -172.2(3) . . . . ?
C22 C27 C28 C19 2.9(5) . . . . ?
C26 C27 C28 C38 -0.3(5) . . . . ?
C22 C27 C28 C38 174.9(3) . . . . ?
P1 O6 C29 C38 -72.4(4) . . . . ?
P1 O6 C29 C30 110.4(3) . . . . ?
C38 C29 C30 C31 4.6(6) . . . . ?
O6 C29 C30 C31 -178.3(3) . . . . ?
C29 C30 C31 C32 1.9(6) . . . . ?
C30 C31 C32 C33 175.5(4) . . . . ?
C30 C31 C32 C37 -4.2(6) . . . . ?
C37 C32 C33 C34 1.6(6) . . . . ?
C31 C32 C33 C34 -178.1(4) . . . . ?
C32 C33 C34 C35 -0.3(6) . . . . ?
C33 C34 C35 C36 -0.6(6) . . . . ?
C34 C35 C36 C37 0.0(6) . . . . ?
C35 C36 C37 C32 1.3(5) . . . . ?
C35 C36 C37 C38 178.4(3) . . . . ?
C33 C32 C37 C36 -2.1(5) . . . . ?
C31 C32 C37 C36 177.6(3) . . . . ?
C33 C32 C37 C38 -179.3(3) . . . . ?
C31 C32 C37 C38 0.4(5) . . . . ?
O6 C29 C38 C37 174.6(3) . . . . ?
C30 C29 C38 C37 -8.3(5) . . . . ?
O6 C29 C38 C28 -5.3(5) . . . . ?
C30 C29 C38 C28 171.7(3) . . . . ?
C36 C37 C38 C29 -171.5(3) . . . . ?
C32 C37 C38 C29 5.6(5) . . . . ?
C36 C37 C38 C28 8.5(5) . . . . ?
C32 C37 C38 C28 -174.4(3) . . . . ?
C19 C28 C38 C29 53.7(5) . . . . ?
C27 C28 C38 C29 -118.1(4) . . . . ?
C19 C28 C38 C37 -126.2(4) . . . . ?
C27 C28 C38 C37 62.0(5) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1 O3 0.93 1.71 2.627(4) 168.5 1_655

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        68.32
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.265
_refine_diff_density_min         -0.501
_refine_diff_density_rms         0.061
