# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2018

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

data_exp_21689
_database_code_depnum_ccdc_archive 'CCDC 1832435'
_audit_update_record             
;
2018-03-26 deposited with the CCDC.
2018-05-08 downloaded from the CCDC.
;
_audit_creation_date             2018-01-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C32 H23 Cl2 P'
_chemical_formula_sum            'C32 H23 Cl2 P'
_chemical_formula_weight         509.37
_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'
Cl Cl 0.3639 0.7018 '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'

_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           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   13.4074(4)
_cell_length_b                   11.4312(3)
_cell_length_c                   18.1544(5)
_cell_angle_alpha                90
_cell_angle_beta                 110.539(3)
_cell_angle_gamma                90
_cell_volume                     2605.52(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3981
_cell_measurement_temperature    296.80(10)
_cell_measurement_theta_max      60.2890
_cell_measurement_theta_min      5.1560
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.956
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64381
_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_absorpt_special_details   ?
_exptl_crystal_density_diffrn    1.299
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       white
_exptl_crystal_F_000             1056
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0263
_diffrn_reflns_av_unetI/netI     0.0330
_diffrn_reflns_Laue_measured_fraction_full 0.969
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            7481
_diffrn_reflns_point_group_measured_fraction_full 0.969
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_theta_full        60.515
_diffrn_reflns_theta_max         60.515
_diffrn_reflns_theta_min         4.661
_diffrn_ambient_temperature      296.80(10)
_diffrn_detector_area_resol_mean 16.0855
_diffrn_measured_fraction_theta_full 0.969
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   35.00   60.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  178.0000 -180.0000 25

#__ type_ start__ end____ width___ exp.time_
  2 omega   21.00   47.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -99.0000  120.0000 26

#__ type_ start__ end____ width___ exp.time_
  3 omega   35.00   60.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  178.0000 -120.0000 25

#__ type_ start__ end____ width___ exp.time_
  4 omega   55.00   89.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  178.0000    0.0000 34

#__ type_ start__ end____ width___ exp.time_
  5 omega  -20.00    5.00   1.0000    3.5000
omega____ theta____ kappa____ phi______ frames
    -        0.0000  -99.0000  120.0000 25

#__ type_ start__ end____ width___ exp.time_
  6 omega -114.00  -40.00   1.0000   14.0000
omega____ theta____ kappa____ phi______ frames
    -      -46.8863  125.0000 -180.0000 74

#__ type_ start__ end____ width___ exp.time_
  7 omega   60.00  118.00   1.0000   14.0000
omega____ theta____ kappa____ phi______ frames
    -       46.8863   57.0000  -60.0000 58

#__ type_ start__ end____ width___ exp.time_
  8 omega   36.00   92.00   1.0000   14.0000
omega____ theta____ kappa____ phi______ frames
    -       46.8863   57.0000    0.0000 56

#__ type_ start__ end____ width___ exp.time_
  9 omega   75.00  124.00   1.0000   14.0000
omega____ theta____ kappa____ phi______ frames
    -       46.8863  125.0000 -120.0000 49

#__ type_ start__ end____ width___ exp.time_
 10 omega   22.00   48.00   1.0000   14.0000
omega____ theta____ kappa____ phi______ frames
    -       46.8863   57.0000  -60.0000 26

#__ type_ start__ end____ width___ exp.time_
 11 omega   73.00  125.00   1.0000   14.0000
omega____ theta____ kappa____ phi______ frames
    -       46.8863  125.0000  -60.0000 52

#__ type_ start__ end____ width___ exp.time_
 12 omega  -76.00  -21.00   1.0000   16.4100
omega____ theta____ kappa____ phi______ frames
    -      -92.0000   50.0000  -30.0000 55

#__ type_ start__ end____ width___ exp.time_
 13 omega  -71.00  -11.00   1.0000   16.4100
omega____ theta____ kappa____ phi______ frames
    -      -92.0000   25.0000  -60.0000 60

#__ type_ start__ end____ width___ exp.time_
 14 omega  -72.00  -18.00   1.0000   16.4100
omega____ theta____ kappa____ phi______ frames
    -      -92.0000   25.0000 -150.0000 54

#__ type_ start__ end____ width___ exp.time_
 15 omega -164.00 -134.00   1.0000   16.4100
omega____ theta____ kappa____ phi______ frames
    -      -92.0000 -111.0000 -150.0000 30

#__ type_ start__ end____ width___ exp.time_
 16 omega -157.00 -105.00   1.0000   16.4100
omega____ theta____ kappa____ phi______ frames
    -      -92.0000 -111.0000  -90.0000 52

#__ type_ start__ end____ width___ exp.time_
 17 omega   32.00   65.00   1.0000   16.4100
omega____ theta____ kappa____ phi______ frames
    -       93.7727  -37.0000  -60.0000 33

#__ type_ start__ end____ width___ exp.time_
 18 omega   53.00   90.00   1.0000   16.4100
omega____ theta____ kappa____ phi______ frames
    -       93.7727 -111.0000  -30.0000 37

#__ type_ start__ end____ width___ exp.time_
 19 omega   79.00  172.00   1.0000   16.4100
omega____ theta____ kappa____ phi______ frames
    -       93.7727  111.0000  -30.0000 93

#__ type_ start__ end____ width___ exp.time_
 20 omega   22.00   69.00   1.0000   16.4100
omega____ theta____ kappa____ phi______ frames
    -       93.7727  -37.0000   30.0000 47

#__ type_ start__ end____ width___ exp.time_
 21 omega   36.00   90.00   1.0000   16.4100
omega____ theta____ kappa____ phi______ frames
    -       93.7727 -111.0000  -90.0000 54

#__ type_ start__ end____ width___ exp.time_
 22 omega   13.00   58.00   1.0000   16.4100
omega____ theta____ kappa____ phi______ frames
    -       93.7727 -111.0000  120.0000 45
;
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.1086563000
_diffrn_orient_matrix_UB_12      -0.0168597000
_diffrn_orient_matrix_UB_13      -0.0098041000
_diffrn_orient_matrix_UB_21      0.0002410000
_diffrn_orient_matrix_UB_22      0.1299187000
_diffrn_orient_matrix_UB_23      -0.0223971000
_diffrn_orient_matrix_UB_31      0.0570567000
_diffrn_orient_matrix_UB_32      0.0314557000
_diffrn_orient_matrix_UB_33      0.0872903000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance Ultra (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                3345
_reflns_number_total             3800
_reflns_odcompleteness_completeness 98.82
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     58.86
_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, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.212
_refine_diff_density_min         -0.315
_refine_diff_density_rms         0.079
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.092
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     316
_refine_ls_number_reflns         3800
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0470
_refine_ls_R_factor_gt           0.0426
_refine_ls_restrained_S_all      1.092
_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)+(0.0670P)²+0.5420P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1157
_refine_ls_wR_factor_ref         0.1206
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C006(H006), C009(H009), C00C(H00C), C00D(H00D), C00E(H00E), C00G(H00G),
 C00H(H00H), C00I(H00I), C00J(H00J), C00K(H00K), C00L(H00L), C00N(H00N),
 C00P(H00P), C00Q(H00Q), C00R(H00R), C00S(H00S), C00T(H00T), C00U(H00U),
 C00V(H00V), C00W(H00W), C00X(H00X), C00Y(H00Y), C00Z(H00Z)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P01 P 0.13874(5) 0.23313(5) 0.51604(3) 0.0537(2) Uani 1 1 d . . . . .
Cl02 Cl 0.81092(5) 0.30341(7) 0.78338(4) 0.0778(2) Uani 1 1 d . . . . .
Cl03 Cl 0.59347(7) 0.88416(6) 1.12344(4) 0.0860(3) Uani 1 1 d . . . . .
C004 C 0.54570(15) 0.49842(18) 0.82846(11) 0.0446(5) Uani 1 1 d . . . . .
C005 C 0.49159(16) 0.64425(18) 0.91202(12) 0.0473(5) Uani 1 1 d . . . . .
C006 C 0.63033(17) 0.5583(2) 0.81874(12) 0.0525(5) Uani 1 1 d . . . . .
H006 H 0.6323 0.6395 0.8220 0.063 Uiso 1 1 calc R . . . .
C007 C 0.30385(16) 0.47944(19) 0.72855(12) 0.0499(5) Uani 1 1 d . . . . .
C008 C 0.45850(16) 0.56309(18) 0.84343(11) 0.0467(5) Uani 1 1 d . . . . .
C009 C 0.58020(18) 0.6194(2) 0.97842(12) 0.0539(5) Uani 1 1 d . . . . .
H009 H 0.6193 0.5518 0.9793 0.065 Uiso 1 1 calc R . . . .
C00A C 0.00333(18) 0.21588(19) 0.51735(12) 0.0532(5) Uani 1 1 d . . . . .
C00B C 0.19676(16) 0.33903(19) 0.59563(11) 0.0494(5) Uani 1 1 d . . . . .
C00C C 0.35471(17) 0.5490(2) 0.80030(12) 0.0512(5) Uani 1 1 d . . . . .
H00C H 0.3078 0.5893 0.8186 0.061 Uiso 1 1 calc R . . . .
C00D C 0.35182(17) 0.4490(2) 0.67403(12) 0.0515(5) Uani 1 1 d . . . . .
H00D H 0.4200 0.4761 0.6812 0.062 Uiso 1 1 calc R . . . .
C00E C 0.54520(18) 0.37720(19) 0.82440(12) 0.0523(5) Uani 1 1 d . . . . .
H00E H 0.4894 0.3358 0.8312 0.063 Uiso 1 1 calc R . . . .
C00F C 0.70836(18) 0.3794(2) 0.80014(12) 0.0551(6) Uani 1 1 d . . . . .
C00G C 0.29965(17) 0.3795(2) 0.60986(12) 0.0515(5) Uani 1 1 d . . . . .
H00G H 0.3342 0.3592 0.5753 0.062 Uiso 1 1 calc R . . . .
C00H C 0.62583(19) 0.3172(2) 0.81047(13) 0.0572(6) Uani 1 1 d . . . . .
H00H H 0.6248 0.2359 0.8080 0.069 Uiso 1 1 calc R . . . .
C00I C 0.43652(19) 0.7471(2) 0.91247(13) 0.0571(6) Uani 1 1 d . . . . .
H00I H 0.3781 0.7669 0.8684 0.069 Uiso 1 1 calc R . . . .
C00J C 0.71156(17) 0.4994(2) 0.80433(13) 0.0565(6) Uani 1 1 d . . . . .
H00J H 0.7676 0.5405 0.7976 0.068 Uiso 1 1 calc R . . . .
C00K C 0.6114(2) 0.6928(2) 1.04302(13) 0.0599(6) Uani 1 1 d . . . . .
H00K H 0.6705 0.6747 1.0870 0.072 Uiso 1 1 calc R . . . .
C00L C 0.14720(18) 0.3744(2) 0.64727(14) 0.0656(7) Uani 1 1 d . . . . .
H00L H 0.0773 0.3517 0.6382 0.079 Uiso 1 1 calc R . . . .
C00M C 0.11447(17) 0.3205(2) 0.42689(12) 0.0528(5) Uani 1 1 d . . . . .
C00N C 0.19961(18) 0.4426(2) 0.71185(14) 0.0662(7) Uani 1 1 d . . . . .
H00N H 0.1640 0.4647 0.7453 0.079 Uiso 1 1 calc R . . . .
C00O C 0.5541(2) 0.7924(2) 1.04142(13) 0.0584(6) Uani 1 1 d . . . . .
C00P C 0.4668(2) 0.8206(2) 0.97710(14) 0.0629(6) Uani 1 1 d . . . . .
H00P H 0.4284 0.8884 0.9769 0.075 Uiso 1 1 calc R . . . .
C00Q C -0.08011(19) 0.2928(2) 0.48176(14) 0.0626(6) Uani 1 1 d . . . . .
H00Q H -0.0688 0.3579 0.4550 0.075 Uiso 1 1 calc R . . . .
C00R C -0.0169(2) 0.1186(2) 0.55574(15) 0.0697(7) Uani 1 1 d . . . . .
H00R H 0.0374 0.0652 0.5792 0.084 Uiso 1 1 calc R . . . .
C00S C 0.1315(2) 0.4396(2) 0.42503(14) 0.0689(7) Uani 1 1 d . . . . .
H00S H 0.1574 0.4811 0.4720 0.083 Uiso 1 1 calc R . . . .
C00T C 0.0773(2) 0.2627(3) 0.35550(15) 0.0699(7) Uani 1 1 d . . . . .
H00T H 0.0677 0.1821 0.3550 0.084 Uiso 1 1 calc R . . . .
C00U C -0.1800(2) 0.2733(3) 0.48591(17) 0.0735(7) Uani 1 1 d . . . . .
H00U H -0.2350 0.3257 0.4624 0.088 Uiso 1 1 calc R . . . .
C00V C 0.0712(2) 0.4394(3) 0.28469(15) 0.0765(8) Uani 1 1 d . . . . .
H00V H 0.0560 0.4793 0.2374 0.092 Uiso 1 1 calc R . . . .
C00W C 0.1108(2) 0.4984(3) 0.35446(16) 0.0796(8) Uani 1 1 d . . . . .
H00W H 0.1238 0.5783 0.3546 0.095 Uiso 1 1 calc R . . . .
C00X C 0.0539(2) 0.3213(3) 0.28489(16) 0.0835(9) Uani 1 1 d . . . . .
H00X H 0.0266 0.2807 0.2376 0.100 Uiso 1 1 calc R . . . .
C00Y C -0.1980(2) 0.1767(3) 0.52468(18) 0.0816(8) Uani 1 1 d . . . . .
H00Y H -0.2652 0.1637 0.5271 0.098 Uiso 1 1 calc R . . . .
C00Z C -0.1172(3) 0.1002(3) 0.55949(19) 0.0867(9) Uani 1 1 d . . . . .
H00Z H -0.1294 0.0352 0.5859 0.104 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
P01 C00A 1.835(2) . ?
P01 C00B 1.836(2) . ?
P01 C00M 1.831(2) . ?
Cl02 C00F 1.741(2) . ?
Cl03 C00O 1.745(2) . ?
C004 C006 1.388(3) . ?
C004 C008 1.487(3) . ?
C004 C00E 1.388(3) . ?
C005 C008 1.490(3) . ?
C005 C009 1.393(3) . ?
C005 C00I 1.390(3) . ?
C006 H006 0.9300 . ?
C006 C00J 1.381(3) . ?
C007 C00C 1.473(3) . ?
C007 C00D 1.400(3) . ?
C007 C00N 1.387(3) . ?
C008 C00C 1.346(3) . ?
C009 H009 0.9300 . ?
C009 C00K 1.382(3) . ?
C00A C00Q 1.391(3) . ?
C00A C00R 1.389(3) . ?
C00B C00G 1.391(3) . ?
C00B C00L 1.386(3) . ?
C00C H00C 0.9300 . ?
C00D H00D 0.9300 . ?
C00D C00G 1.381(3) . ?
C00E H00E 0.9300 . ?
C00E C00H 1.377(3) . ?
C00F C00H 1.382(3) . ?
C00F C00J 1.374(3) . ?
C00G H00G 0.9300 . ?
C00H H00H 0.9300 . ?
C00I H00I 0.9300 . ?
C00I C00P 1.383(3) . ?
C00J H00J 0.9300 . ?
C00K H00K 0.9300 . ?
C00K C00O 1.368(4) . ?
C00L H00L 0.9300 . ?
C00L C00N 1.378(3) . ?
C00M C00S 1.383(4) . ?
C00M C00T 1.383(3) . ?
C00N H00N 0.9300 . ?
C00O C00P 1.370(4) . ?
C00P H00P 0.9300 . ?
C00Q H00Q 0.9300 . ?
C00Q C00U 1.385(4) . ?
C00R H00R 0.9300 . ?
C00R C00Z 1.386(4) . ?
C00S H00S 0.9300 . ?
C00S C00W 1.385(4) . ?
C00T H00T 0.9300 . ?
C00T C00X 1.382(4) . ?
C00U H00U 0.9300 . ?
C00U C00Y 1.375(4) . ?
C00V H00V 0.9300 . ?
C00V C00W 1.367(4) . ?
C00V C00X 1.370(4) . ?
C00W H00W 0.9300 . ?
C00X H00X 0.9300 . ?
C00Y H00Y 0.9300 . ?
C00Y C00Z 1.363(4) . ?
C00Z H00Z 0.9300 . ?

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
C00A P01 C00B 102.04(10) . . ?
C00M P01 C00A 101.55(10) . . ?
C00M P01 C00B 103.34(10) . . ?
C006 C004 C008 120.55(19) . . ?
C00E C004 C006 118.3(2) . . ?
C00E C004 C008 121.12(19) . . ?
C009 C005 C008 120.6(2) . . ?
C00I C005 C008 121.91(19) . . ?
C00I C005 C009 117.5(2) . . ?
C004 C006 H006 119.4 . . ?
C00J C006 C004 121.2(2) . . ?
C00J C006 H006 119.4 . . ?
C00D C007 C00C 125.04(19) . . ?
C00N C007 C00C 118.36(19) . . ?
C00N C007 C00D 116.59(19) . . ?
C004 C008 C005 116.08(17) . . ?
C00C C008 C004 123.57(18) . . ?
C00C C008 C005 120.32(19) . . ?
C005 C009 H009 119.2 . . ?
C00K C009 C005 121.5(2) . . ?
C00K C009 H009 119.2 . . ?
C00Q C00A P01 124.35(18) . . ?
C00R C00A P01 117.46(19) . . ?
C00R C00A C00Q 118.2(2) . . ?
C00G C00B P01 118.97(16) . . ?
C00L C00B P01 123.61(17) . . ?
C00L C00B C00G 117.20(19) . . ?
C007 C00C H00C 115.0 . . ?
C008 C00C C007 130.0(2) . . ?
C008 C00C H00C 115.0 . . ?
C007 C00D H00D 119.4 . . ?
C00G C00D C007 121.13(19) . . ?
C00G C00D H00D 119.4 . . ?
C004 C00E H00E 119.4 . . ?
C00H C00E C004 121.2(2) . . ?
C00H C00E H00E 119.4 . . ?
C00H C00F Cl02 119.06(19) . . ?
C00J C00F Cl02 119.78(18) . . ?
C00J C00F C00H 121.2(2) . . ?
C00B C00G H00G 119.2 . . ?
C00D C00G C00B 121.61(19) . . ?
C00D C00G H00G 119.2 . . ?
C00E C00H C00F 119.1(2) . . ?
C00E C00H H00H 120.5 . . ?
C00F C00H H00H 120.5 . . ?
C005 C00I H00I 119.3 . . ?
C00P C00I C005 121.3(2) . . ?
C00P C00I H00I 119.3 . . ?
C006 C00J H00J 120.5 . . ?
C00F C00J C006 119.1(2) . . ?
C00F C00J H00J 120.5 . . ?
C009 C00K H00K 120.4 . . ?
C00O C00K C009 119.1(2) . . ?
C00O C00K H00K 120.4 . . ?
C00B C00L H00L 119.4 . . ?
C00N C00L C00B 121.2(2) . . ?
C00N C00L H00L 119.4 . . ?
C00S C00M P01 125.38(17) . . ?
C00T C00M P01 117.48(19) . . ?
C00T C00M C00S 117.1(2) . . ?
C007 C00N H00N 118.9 . . ?
C00L C00N C007 122.1(2) . . ?
C00L C00N H00N 118.9 . . ?
C00K C00O Cl03 118.88(19) . . ?
C00K C00O C00P 121.3(2) . . ?
C00P C00O Cl03 119.9(2) . . ?
C00I C00P H00P 120.4 . . ?
C00O C00P C00I 119.3(2) . . ?
C00O C00P H00P 120.4 . . ?
C00A C00Q H00Q 119.7 . . ?
C00U C00Q C00A 120.5(2) . . ?
C00U C00Q H00Q 119.7 . . ?
C00A C00R H00R 119.7 . . ?
C00Z C00R C00A 120.7(3) . . ?
C00Z C00R H00R 119.7 . . ?
C00M C00S H00S 119.4 . . ?
C00M C00S C00W 121.2(2) . . ?
C00W C00S H00S 119.4 . . ?
C00M C00T H00T 119.1 . . ?
C00X C00T C00M 121.8(3) . . ?
C00X C00T H00T 119.1 . . ?
C00Q C00U H00U 119.9 . . ?
C00Y C00U C00Q 120.2(3) . . ?
C00Y C00U H00U 119.9 . . ?
C00W C00V H00V 120.2 . . ?
C00W C00V C00X 119.6(3) . . ?
C00X C00V H00V 120.2 . . ?
C00S C00W H00W 119.9 . . ?
C00V C00W C00S 120.3(3) . . ?
C00V C00W H00W 119.9 . . ?
C00T C00X H00X 120.1 . . ?
C00V C00X C00T 119.8(3) . . ?
C00V C00X H00X 120.1 . . ?
C00U C00Y H00Y 120.1 . . ?
C00Z C00Y C00U 119.9(3) . . ?
C00Z C00Y H00Y 120.1 . . ?
C00R C00Z H00Z 119.8 . . ?
C00Y C00Z C00R 120.5(3) . . ?
C00Y C00Z H00Z 119.8 . . ?

_shelx_SHELXL_version_number     2014/7

_olex2_submission_special_instructions 'No special instructions were received'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_exp_21119
_database_code_depnum_ccdc_archive 'CCDC 1832437'
_audit_update_record             
;
2018-03-26 deposited with the CCDC.
2018-05-08 downloaded from the CCDC.
;
_audit_creation_date             2018-01-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2016.09.09 svn.r3337 for OlexSys, GUI svn.r5227)
;
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C32 H23 Cl2 O P'
_chemical_formula_sum            'C32 H23 Cl2 O P'
_chemical_formula_weight         525.37
_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'
Cl Cl 0.3639 0.7018 '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'

_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           7
_space_group_name_H-M_alt        'P 1 c 1'
_space_group_name_Hall           'P -2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'

_cell_length_a                   27.1771(4)
_cell_length_b                   9.16128(15)
_cell_length_c                   10.88636(13)
_cell_angle_alpha                90
_cell_angle_beta                 98.5848(13)
_cell_angle_gamma                90
_cell_volume                     2680.08(7)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4680
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      62.5350
_cell_measurement_theta_min      3.2810
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    2.919
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.46393
_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_absorpt_special_details   ?
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       white
_exptl_crystal_F_000             1088
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0211
_diffrn_reflns_av_unetI/netI     0.0271
_diffrn_reflns_Laue_measured_fraction_full 0.977
_diffrn_reflns_Laue_measured_fraction_max 0.977
_diffrn_reflns_limit_h_max       28
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            9425
_diffrn_reflns_point_group_measured_fraction_full 0.550
_diffrn_reflns_point_group_measured_fraction_max 0.550
_diffrn_reflns_theta_full        62.570
_diffrn_reflns_theta_max         62.570
_diffrn_reflns_theta_min         3.289
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 16.0855
_diffrn_measured_fraction_theta_full 0.977
_diffrn_measured_fraction_theta_max 0.977
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -19.00   76.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -       34.2729  -99.0000    0.0000 95

#__ type_ start__ end____ width___ exp.time_
  2 omega  -38.00   58.00   1.0000   11.0000
omega____ theta____ kappa____ phi______ frames
    -       34.2729  -37.0000   30.0000 96

#__ type_ start__ end____ width___ exp.time_
  3 omega   69.00   99.00   1.0000   44.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -93.0000 -109.8915 30

#__ type_ start__ end____ width___ exp.time_
  4 omega   92.00  120.00   1.0000   44.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -93.0000  136.9427 28

#__ type_ start__ end____ width___ exp.time_
  5 omega   97.00  123.00   1.0000   44.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  178.0000 -180.0000 26

#__ type_ start__ end____ width___ exp.time_
  6 omega   95.00  145.00   1.0000   44.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000   61.0000  -90.0000 50

#__ type_ start__ end____ width___ exp.time_
  7 omega   80.00  107.00   1.0000   44.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  111.0000 -150.0000 27

#__ type_ start__ end____ width___ exp.time_
  8 omega   21.00   54.00   1.0000   44.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -93.0000  136.9427 33

#__ type_ start__ end____ width___ exp.time_
  9 omega  110.00  147.00   1.0000   44.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  111.0000 -150.0000 37

#__ type_ start__ end____ width___ exp.time_
 10 omega   52.00   88.00   1.0000   44.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  178.0000 -180.0000 36

#__ type_ start__ end____ width___ exp.time_
 11 omega   22.00   64.00   1.0000   44.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -93.0000 -109.8915 42

#__ type_ start__ end____ width___ exp.time_
 12 omega   70.00  149.00   1.0000   44.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000   61.0000 -150.0000 79

#__ type_ start__ end____ width___ exp.time_
 13 omega   23.00   67.00   1.0000   44.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -45.0000  -90.0000 44

#__ type_ start__ end____ width___ exp.time_
 14 omega   61.00   98.00   1.0000   44.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -61.0000 -150.0000 37

#__ type_ start__ end____ width___ exp.time_
 15 omega   19.00  117.00   1.0000   44.0000
omega____ theta____ kappa____ phi______ frames
    -       90.5000  -91.0000   39.1885 98
;
_diffrn_measurement_device_type  'Xcalibur, Sapphire3, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      0.0272460000
_diffrn_orient_matrix_UB_12      0.1478401000
_diffrn_orient_matrix_UB_13      0.0146770000
_diffrn_orient_matrix_UB_21      -0.0502507000
_diffrn_orient_matrix_UB_22      0.0800994000
_diffrn_orient_matrix_UB_23      -0.0294908000
_diffrn_orient_matrix_UB_31      -0.0047029000
_diffrn_orient_matrix_UB_32      0.0013229000
_diffrn_orient_matrix_UB_33      0.1392210000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'Enhance Ultra (Cu) X-ray Source'
_reflns_Friedel_coverage         0.125
_reflns_Friedel_fraction_full    0.122
_reflns_Friedel_fraction_max     0.122
_reflns_number_gt                4244
_reflns_number_total             4731
_reflns_odcompleteness_completeness 99.11
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     58.86
_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, 2015)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2015)'
_refine_diff_density_max         0.203
_refine_diff_density_min         -0.298
_refine_diff_density_rms         0.033
_refine_ls_abs_structure_details 
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   0.04(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     649
_refine_ls_number_reflns         4731
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0391
_refine_ls_R_factor_gt           0.0351
_refine_ls_restrained_S_all      1.051
_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)+(0.0594P)²+0.3980P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0974
_refine_ls_wR_factor_ref         0.1019
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C46(H46), C2(H2), C47(H47), C49(H49), C32(H32), C54(H54), C3(H3), C12(H12),
 C6(H6), C17(H17), C60(H60), C8(H8), C50(H50), C55(H55), C19(H19), C14(H14),
 C51(H51), C10(H10), C37(H37), C31(H31), C25(H25), C36(H36), C61(H61), C28(H28),
  C26(H26), C38(H38), C58(H58), C15(H15), C29(H29), C35(H35), C11(H11), C5(H5),
 C9(H9), C4(H4), C63(H63), C64(H64), C57(H57), C18(H18), C22(H22), C34(H34),
 C44(H44), C40(H40), C23(H23), C43(H43), C41(H41), C42(H42)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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
P2 P 0.80247(5) 0.38616(17) 0.69536(11) 0.0452(3) Uani 1 1 d . . . . .
P1 P 0.54603(5) 0.88626(17) 0.54273(11) 0.0455(3) Uani 1 1 d . . . . .
O1 O 0.55161(18) 0.8328(6) 0.6739(4) 0.0569(11) Uani 1 1 d . . . . .
C46 C 0.8611(2) 0.6108(7) 0.8266(6) 0.0503(15) Uani 1 1 d . . . . .
H46 H 0.8352 0.6271 0.8720 0.060 Uiso 1 1 calc R . . . .
C45 C 0.8550(2) 0.5037(7) 0.7336(5) 0.0429(13) Uani 1 1 d . . . . .
C7 C 0.5997(2) 0.9883(8) 0.5134(6) 0.0502(14) Uani 1 1 d . . . . .
C2 C 0.5498(3) 0.6010(8) 0.4690(7) 0.0636(19) Uani 1 1 d . . . . .
H2 H 0.5630 0.5861 0.5519 0.076 Uiso 1 1 calc R . . . .
C47 C 0.9037(2) 0.6927(8) 0.8537(6) 0.0525(15) Uani 1 1 d . . . . .
H47 H 0.9067 0.7625 0.9164 0.063 Uiso 1 1 calc R . . . .
C49 C 0.9371(3) 0.5669(9) 0.6938(7) 0.0614(17) Uani 1 1 d . . . . .
H49 H 0.9629 0.5521 0.6480 0.074 Uiso 1 1 calc R . . . .
C32 C 0.2523(3) 1.4673(9) 0.4810(9) 0.077(2) Uani 1 1 d . . . . .
H32 H 0.2666 1.5079 0.5562 0.092 Uiso 1 1 calc R . . . .
C54 C 1.0958(3) 0.7899(9) 0.9170(7) 0.0643(18) Uani 1 1 d . . . . .
H54 H 1.0829 0.7051 0.9466 0.077 Uiso 1 1 calc R . . . .
C3 C 0.5446(4) 0.4841(9) 0.3919(9) 0.079(2) Uani 1 1 d . . . . .
H3 H 0.5563 0.3926 0.4196 0.095 Uiso 1 1 calc R . . . .
C12 C 0.6300(3) 0.9369(10) 0.4303(7) 0.070(2) Uani 1 1 d . . . . .
H12 H 0.6209 0.8559 0.3807 0.084 Uiso 1 1 calc R . . . .
C6 C 0.5159(3) 0.7595(9) 0.3102(7) 0.0657(19) Uani 1 1 d . . . . .
H6 H 0.5061 0.8527 0.2830 0.079 Uiso 1 1 calc R . . . .
C1 C 0.5369(2) 0.7374(7) 0.4319(5) 0.0474(13) Uani 1 1 d . . . . .
C17 C 0.4438(3) 1.1877(8) 0.3914(6) 0.0538(16) Uani 1 1 d . . . . .
H17 H 0.4403 1.2555 0.3271 0.065 Uiso 1 1 calc R . . . .
C59 C 1.0149(3) 0.7892(9) 0.6113(7) 0.0631(18) Uani 1 1 d . . . . .
C60 C 1.0514(4) 0.7214(14) 0.5485(9) 0.102(3) Uani 1 1 d . . . . .
H60 H 1.0793 0.6743 0.5905 0.122 Uiso 1 1 calc R . . . .
C16 C 0.4050(3) 1.1700(7) 0.4558(6) 0.0517(15) Uani 1 1 d . . . . .
C53 C 1.0722(3) 0.8526(9) 0.8115(6) 0.0586(17) Uani 1 1 d . . . . .
C8 C 0.6131(4) 1.1062(11) 0.5776(8) 0.093(3) Uani 1 1 d . . . . .
H8 H 0.5923 1.1437 0.6303 0.111 Uiso 1 1 calc R . . . .
C48 C 0.9435(3) 0.6681(8) 0.7831(6) 0.0571(17) Uani 1 1 d . . . . .
C50 C 0.8951(3) 0.4831(8) 0.6648(6) 0.0568(16) Uani 1 1 d . . . . .
H50 H 0.8929 0.4142 0.6014 0.068 Uiso 1 1 calc R . . . .
C55 C 1.1398(3) 0.8518(10) 0.9829(7) 0.073(2) Uani 1 1 d . . . . .
H55 H 1.1546 0.8137 1.0587 0.087 Uiso 1 1 calc R . . . .
C27 C 0.2750(3) 1.3500(8) 0.4311(7) 0.0618(17) Uani 1 1 d . . . . .
C19 C 0.3571(3) 1.2477(8) 0.4208(7) 0.0628(18) Uani 1 1 d . . . . .
H19 H 0.3490 1.2683 0.3365 0.075 Uiso 1 1 calc R . . . .
C20 C 0.3237(3) 1.2929(8) 0.4912(6) 0.0592(17) Uani 1 1 d . . . . .
C62 C 0.9986(4) 0.7921(11) 0.3536(8) 0.084(3) Uani 1 1 d . . . . .
C14 C 0.4539(2) 0.9826(7) 0.5722(6) 0.0517(15) Uani 1 1 d . . . . .
H14 H 0.4573 0.9097 0.6324 0.062 Uiso 1 1 calc R . . . .
C51 C 0.9896(3) 0.7500(9) 0.8200(7) 0.0635(18) Uani 1 1 d . . . . .
H51 H 0.9963 0.7763 0.9033 0.076 Uiso 1 1 calc R . . . .
C30 C 0.1876(3) 1.4709(10) 0.3047(7) 0.069(2) Uani 1 1 d . . . . .
C10 C 0.6861(4) 1.1392(11) 0.4921(10) 0.098(3) Uani 1 1 d . . . . .
H10 H 0.7136 1.1953 0.4811 0.117 Uiso 1 1 calc R . . . .
C37 C 0.6939(4) 0.6902(11) 0.6786(9) 0.092(3) Uani 1 1 d . . . . .
H37 H 0.6863 0.7792 0.6393 0.111 Uiso 1 1 calc R . . . .
C31 C 0.2089(3) 1.5227(10) 0.4196(9) 0.083(3) Uani 1 1 d . . . . .
H31 H 0.1932 1.5977 0.4562 0.100 Uiso 1 1 calc R . . . .
C13 C 0.4921(2) 1.0057(7) 0.5086(6) 0.0484(14) Uani 1 1 d . . . . .
C25 C 0.3845(4) 1.3562(10) 0.8245(8) 0.078(2) Uani 1 1 d . . . . .
H25 H 0.4129 1.4002 0.8671 0.094 Uiso 1 1 calc R . . . .
C36 C 0.6615(3) 0.6271(10) 0.7578(8) 0.079(2) Uani 1 1 d . . . . .
H36 H 0.6305 0.6682 0.7615 0.094 Uiso 1 1 calc R . . . .
C61 C 1.0419(4) 0.7316(12) 0.4173(9) 0.100(3) Uani 1 1 d . . . . .
H61 H 1.0657 0.6962 0.3718 0.120 Uiso 1 1 calc R . . . .
C28 C 0.2516(3) 1.2969(9) 0.3144(7) 0.070(2) Uani 1 1 d . . . . .
H28 H 0.2667 1.2218 0.2762 0.084 Uiso 1 1 calc R . . . .
C33 C 0.7488(3) 0.4833(7) 0.7297(6) 0.0541(15) Uani 1 1 d . . . . .
C26 C 0.3745(4) 1.3537(11) 0.6947(9) 0.080(2) Uani 1 1 d . . . . .
H26 H 0.3973 1.3967 0.6502 0.096 Uiso 1 1 calc R . . . .
C38 C 0.7356(3) 0.6170(8) 0.6631(8) 0.075(2) Uani 1 1 d . . . . .
H38 H 0.7560 0.6531 0.6088 0.090 Uiso 1 1 calc R . . . .
C52 C 1.0236(2) 0.7923(8) 0.7491(7) 0.0625(18) Uani 1 1 d . . . . .
C21 C 0.3323(3) 1.2902(9) 0.6294(7) 0.0626(18) Uani 1 1 d . . . . .
C58 C 1.0957(3) 0.9647(9) 0.7593(8) 0.070(2) Uani 1 1 d . . . . .
H58 H 1.0821 0.9983 0.6809 0.085 Uiso 1 1 calc R . . . .
C15 C 0.4101(3) 1.0613(8) 0.5529(7) 0.0581(17) Uani 1 1 d . . . . .
H15 H 0.3849 1.0450 0.6005 0.070 Uiso 1 1 calc R . . . .
C56 C 1.1601(3) 0.9705(8) 0.9304(7) 0.0612(18) Uani 1 1 d . . . . .
C29 C 0.2080(3) 1.3521(10) 0.2569(8) 0.074(2) Uani 1 1 d . . . . .
H29 H 0.1919 1.3088 0.1846 0.088 Uiso 1 1 calc R . . . .
C35 C 0.6760(3) 0.5115(12) 0.8245(8) 0.089(3) Uani 1 1 d . . . . .
H35 H 0.6574 0.4802 0.8845 0.106 Uiso 1 1 calc R . . . .
C24 C 0.3483(5) 1.2871(13) 0.8874(9) 0.100(3) Uani 1 1 d . . . . .
C11 C 0.6753(3) 1.0116(12) 0.4234(10) 0.094(3) Uani 1 1 d . . . . .
H11 H 0.6975 0.9758 0.3736 0.112 Uiso 1 1 calc R . . . .
C5 C 0.5096(4) 0.6441(10) 0.2292(7) 0.075(2) Uani 1 1 d . . . . .
H5 H 0.4972 0.6597 0.1459 0.090 Uiso 1 1 calc R . . . .
C9 C 0.6585(4) 1.1777(13) 0.5687(10) 0.111(4) Uani 1 1 d . . . . .
H9 H 0.6681 1.2558 0.6214 0.133 Uiso 1 1 calc R . . . .
C4 C 0.5218(4) 0.5041(11) 0.2719(9) 0.084(3) Uani 1 1 d . . . . .
H4 H 0.5145 0.4243 0.2195 0.101 Uiso 1 1 calc R . . . .
C63 C 0.9669(5) 0.8470(12) 0.4167(10) 0.103(3) Uani 1 1 d . . . . .
H63 H 0.9379 0.8867 0.3732 0.124 Uiso 1 1 calc R . . . .
C64 C 0.9727(3) 0.8512(10) 0.5434(7) 0.072(2) Uani 1 1 d . . . . .
H64 H 0.9487 0.8950 0.5838 0.086 Uiso 1 1 calc R . . . .
C57 C 1.1394(3) 1.0306(9) 0.8206(8) 0.071(2) Uani 1 1 d . . . . .
H57 H 1.1535 1.1113 0.7874 0.085 Uiso 1 1 calc R . . . .
C18 C 0.4885(2) 1.1102(6) 0.4160(6) 0.0482(15) Uani 1 1 d . . . . .
H18 H 0.5147 1.1282 0.3719 0.058 Uiso 1 1 calc R . . . .
C22 C 0.2998(3) 1.2348(10) 0.6992(8) 0.080(2) Uani 1 1 d . . . . .
H22 H 0.2693 1.2030 0.6578 0.096 Uiso 1 1 calc R . . . .
C34 C 0.7175(3) 0.4363(10) 0.8080(9) 0.076(2) Uani 1 1 d . . . . .
H34 H 0.7249 0.3498 0.8517 0.091 Uiso 1 1 calc R . . . .
Cl4 Cl 1.21450(9) 1.0504(3) 1.0102(2) 0.0953(8) Uani 1 1 d . . . . .
Cl2 Cl 0.13400(9) 1.5476(3) 0.2263(2) 0.0941(7) Uani 1 1 d . . . . .
Cl3 Cl 0.98856(14) 0.7968(4) 0.1908(2) 0.1290(11) Uani 1 1 d . . . . .
Cl1 Cl 0.35612(14) 1.2859(4) 1.0473(2) 0.1448(14) Uani 1 1 d . . . . .
O2 O 0.79829(19) 0.3308(5) 0.5671(4) 0.0594(12) Uani 1 1 d . . . . .
C44 C 0.7948(3) 0.0991(7) 0.7636(7) 0.0584(17) Uani 1 1 d . . . . .
H44 H 0.7783 0.0849 0.6834 0.070 Uiso 1 1 calc R . . . .
C39 C 0.8114(2) 0.2403(7) 0.8071(6) 0.0493(14) Uani 1 1 d . . . . .
C40 C 0.8328(3) 0.2573(9) 0.9302(7) 0.0657(19) Uani 1 1 d . . . . .
H40 H 0.8426 0.3498 0.9595 0.079 Uiso 1 1 calc R . . . .
C23 C 0.3080(5) 1.2213(15) 0.8265(10) 0.114(4) Uani 1 1 d . . . . .
H23 H 0.2864 1.1686 0.8684 0.137 Uiso 1 1 calc R . . . .
C43 C 0.8047(3) -0.0190(9) 0.8486(8) 0.074(2) Uani 1 1 d . . . . .
H43 H 0.7970 -0.1135 0.8209 0.089 Uiso 1 1 calc R . . . .
C41 C 0.8399(4) 0.1383(10) 1.0106(9) 0.081(2) Uani 1 1 d . . . . .
H41 H 0.8548 0.1516 1.0925 0.098 Uiso 1 1 calc R . . . .
C42 C 0.8252(3) 0.0020(9) 0.9693(8) 0.073(2) Uani 1 1 d . . . . .
H42 H 0.8291 -0.0767 1.0238 0.087 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
P2 C45 1.787(7) . ?
P2 C33 1.796(8) . ?
P2 O2 1.474(5) . ?
P2 C39 1.799(7) . ?
P1 O1 1.496(5) . ?
P1 C7 1.801(7) . ?
P1 C1 1.813(6) . ?
P1 C13 1.822(7) . ?
C46 C45 1.401(9) . ?
C46 C47 1.374(9) . ?
C45 C50 1.425(9) . ?
C7 C12 1.394(11) . ?
C7 C8 1.308(11) . ?
C2 C3 1.355(12) . ?
C2 C1 1.344(10) . ?
C47 C48 1.435(10) . ?
C49 C48 1.335(10) . ?
C49 C50 1.371(11) . ?
C32 C27 1.390(11) . ?
C32 C31 1.363(12) . ?
C54 C53 1.356(10) . ?
C54 C55 1.419(10) . ?
C3 C4 1.373(13) . ?
C12 C11 1.419(12) . ?
C6 C1 1.376(10) . ?
C6 C5 1.371(11) . ?
C17 C16 1.361(10) . ?
C17 C18 1.398(9) . ?
C59 C60 1.429(13) . ?
C59 C52 1.484(11) . ?
C59 C64 1.390(11) . ?
C60 C61 1.416(13) . ?
C16 C19 1.482(9) . ?
C16 C15 1.443(9) . ?
C53 C52 1.497(10) . ?
C53 C58 1.376(11) . ?
C8 C9 1.411(13) . ?
C48 C51 1.464(10) . ?
C55 C56 1.381(11) . ?
C27 C20 1.482(10) . ?
C27 C28 1.420(11) . ?
C19 C20 1.339(10) . ?
C20 C21 1.487(10) . ?
C62 C61 1.389(14) . ?
C62 C63 1.284(16) . ?
C62 Cl3 1.753(9) . ?
C14 C13 1.348(9) . ?
C14 C15 1.381(10) . ?
C51 C52 1.346(10) . ?
C30 C31 1.382(12) . ?
C30 C29 1.359(12) . ?
C30 Cl2 1.723(8) . ?
C10 C11 1.395(15) . ?
C10 C9 1.253(15) . ?
C37 C36 1.443(14) . ?
C37 C38 1.348(12) . ?
C13 C18 1.384(9) . ?
C25 C26 1.399(12) . ?
C25 C24 1.427(16) . ?
C36 C35 1.311(13) . ?
C28 C29 1.354(11) . ?
C33 C38 1.441(10) . ?
C33 C34 1.360(12) . ?
C26 C21 1.384(11) . ?
C21 C22 1.346(12) . ?
C58 C57 1.410(12) . ?
C56 C57 1.359(11) . ?
C56 Cl4 1.759(7) . ?
C35 C34 1.357(11) . ?
C24 Cl1 1.722(10) . ?
C24 C23 1.337(16) . ?
C5 C4 1.388(13) . ?
C63 C64 1.365(13) . ?
C22 C23 1.377(13) . ?
C44 C39 1.427(9) . ?
C44 C43 1.423(11) . ?
C39 C40 1.387(9) . ?
C40 C41 1.394(11) . ?
C43 C42 1.362(12) . ?
C41 C42 1.366(12) . ?

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
C45 P2 C33 107.4(3) . . ?
C45 P2 C39 105.5(3) . . ?
C33 P2 C39 105.0(3) . . ?
O2 P2 C45 112.0(3) . . ?
O2 P2 C33 114.7(3) . . ?
O2 P2 C39 111.6(3) . . ?
O1 P1 C7 111.7(3) . . ?
O1 P1 C1 111.9(3) . . ?
O1 P1 C13 110.8(3) . . ?
C7 P1 C1 107.9(3) . . ?
C7 P1 C13 107.5(3) . . ?
C1 P1 C13 106.8(3) . . ?
C47 C46 C45 122.9(6) . . ?
C46 C45 P2 126.5(5) . . ?
C46 C45 C50 117.1(6) . . ?
C50 C45 P2 116.4(5) . . ?
C12 C7 P1 120.9(6) . . ?
C8 C7 P1 120.1(6) . . ?
C8 C7 C12 118.8(8) . . ?
C1 C2 C3 123.4(7) . . ?
C46 C47 C48 118.5(6) . . ?
C48 C49 C50 124.8(6) . . ?
C31 C32 C27 119.9(8) . . ?
C53 C54 C55 121.0(8) . . ?
C2 C3 C4 118.3(8) . . ?
C7 C12 C11 118.2(8) . . ?
C5 C6 C1 120.0(8) . . ?
C2 C1 P1 119.7(5) . . ?
C2 C1 C6 118.6(6) . . ?
C6 C1 P1 121.7(5) . . ?
C16 C17 C18 124.0(6) . . ?
C60 C59 C52 118.3(7) . . ?
C64 C59 C60 120.0(8) . . ?
C64 C59 C52 121.6(7) . . ?
C61 C60 C59 114.8(9) . . ?
C17 C16 C19 121.9(6) . . ?
C17 C16 C15 117.5(6) . . ?
C15 C16 C19 120.3(6) . . ?
C54 C53 C52 120.1(7) . . ?
C54 C53 C58 118.4(7) . . ?
C58 C53 C52 121.3(7) . . ?
C7 C8 C9 121.5(9) . . ?
C47 C48 C51 117.1(6) . . ?
C49 C48 C47 118.1(6) . . ?
C49 C48 C51 124.7(6) . . ?
C49 C50 C45 118.6(6) . . ?
C56 C55 C54 117.6(8) . . ?
C32 C27 C20 121.4(7) . . ?
C32 C27 C28 116.7(7) . . ?
C28 C27 C20 121.7(6) . . ?
C20 C19 C16 130.2(7) . . ?
C27 C20 C21 116.6(6) . . ?
C19 C20 C27 119.6(6) . . ?
C19 C20 C21 123.8(6) . . ?
C61 C62 Cl3 120.5(9) . . ?
C63 C62 C61 118.4(9) . . ?
C63 C62 Cl3 121.0(9) . . ?
C13 C14 C15 123.5(6) . . ?
C52 C51 C48 128.5(7) . . ?
C31 C30 Cl2 121.2(7) . . ?
C29 C30 C31 118.8(8) . . ?
C29 C30 Cl2 120.0(6) . . ?
C9 C10 C11 119.6(8) . . ?
C38 C37 C36 118.4(9) . . ?
C32 C31 C30 122.1(8) . . ?
C14 C13 P1 117.3(5) . . ?
C14 C13 C18 120.4(6) . . ?
C18 C13 P1 122.2(5) . . ?
C26 C25 C24 115.7(9) . . ?
C35 C36 C37 119.6(8) . . ?
C62 C61 C60 122.9(9) . . ?
C29 C28 C27 122.0(7) . . ?
C38 C33 P2 117.7(6) . . ?
C34 C33 P2 125.2(6) . . ?
C34 C33 C38 117.0(8) . . ?
C21 C26 C25 123.2(10) . . ?
C37 C38 C33 120.7(9) . . ?
C59 C52 C53 117.6(6) . . ?
C51 C52 C59 123.7(6) . . ?
C51 C52 C53 118.7(7) . . ?
C26 C21 C20 120.4(8) . . ?
C22 C21 C20 124.0(7) . . ?
C22 C21 C26 115.5(8) . . ?
C53 C58 C57 122.3(7) . . ?
C14 C15 C16 117.3(6) . . ?
C55 C56 Cl4 118.7(6) . . ?
C57 C56 C55 123.1(7) . . ?
C57 C56 Cl4 118.2(6) . . ?
C28 C29 C30 120.1(7) . . ?
C36 C35 C34 121.6(9) . . ?
C25 C24 Cl1 119.9(10) . . ?
C23 C24 C25 122.3(9) . . ?
C23 C24 Cl1 117.8(10) . . ?
C10 C11 C12 119.4(8) . . ?
C6 C5 C4 119.8(8) . . ?
C10 C9 C8 122.1(9) . . ?
C3 C4 C5 119.6(7) . . ?
C62 C63 C64 124.5(10) . . ?
C63 C64 C59 119.2(9) . . ?
C56 C57 C58 116.8(7) . . ?
C13 C18 C17 117.1(6) . . ?
C21 C22 C23 125.6(9) . . ?
C35 C34 C33 122.1(9) . . ?
C43 C44 C39 117.0(7) . . ?
C44 C39 P2 116.4(5) . . ?
C40 C39 P2 124.4(5) . . ?
C40 C39 C44 119.2(6) . . ?
C39 C40 C41 121.2(8) . . ?
C24 C23 C22 117.1(10) . . ?
C42 C43 C44 122.0(7) . . ?
C42 C41 C40 120.1(9) . . ?
C43 C42 C41 120.3(7) . . ?

_shelx_SHELXL_version_number     2014/7

_olex2_submission_special_instructions 'No special instructions were received'
