# Electronic Supplementary Material (ESI) for Dalton Transactions.
# 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_noel
_database_code_depnum_ccdc_archive 'CCDC 1494780'
_audit_update_record             
;
2016-07-19 deposited with the CCDC.
2018-02-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H32 Br6 Cl2 P2 Se'
_chemical_formula_weight         891.66

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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   P21/n

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

_cell_length_a                   10.1753(2)
_cell_length_b                   19.4723(4)
_cell_length_c                   14.0281(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 97.973(2)
_cell_angle_gamma                90.00
_cell_volume                     2752.61(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    30087
_cell_measurement_theta_min      2.2830
_cell_measurement_theta_max      30.3060

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.3000
_exptl_crystal_size_mid          0.2000
_exptl_crystal_size_min          0.2000
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.152
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1696
_exptl_absorpt_coefficient_mu    10.385
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.74504
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           'Mo K\a'
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur, Eos'
_diffrn_measurement_method       'ω scan'
_diffrn_detector_area_resol_mean 16.1419
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            164062
_diffrn_reflns_av_R_equivalents  0.0603
_diffrn_reflns_av_sigmaI/netI    0.0225
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.28
_diffrn_reflns_theta_max         29.57
_reflns_number_total             7717
_reflns_number_gt                6755
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker XP'
_computing_publication_material  SHELXL-97

_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)+(0.0170P)²+3.7050P] 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_number_reflns         7717
_refine_ls_number_parameters     234
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0339
_refine_ls_R_factor_gt           0.0253
_refine_ls_wR_factor_ref         0.0476
_refine_ls_wR_factor_gt          0.0457
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.063
_refine_ls_shift/su_max          0.002
_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
Se1 Se 0.21806(2) 0.670849(11) 0.566675(16) 0.00978(5) Uani 1 1 d . . .
Br1 Br 0.51268(2) 0.568441(13) 0.606673(18) 0.01759(5) Uani 1 1 d . . .
Br2 Br 0.57763(2) 0.742873(12) 0.557578(18) 0.01508(5) Uani 1 1 d . . .
Br3 Br 0.17748(3) 0.537968(12) 0.547069(17) 0.01631(5) Uani 1 1 d . . .
Br4 Br 0.25527(3) 0.679571(12) 0.390469(17) 0.01577(5) Uani 1 1 d . . .
Br5 Br 0.26187(3) 0.798577(12) 0.593617(18) 0.01678(5) Uani 1 1 d . . .
Br6 Br 0.17526(3) 0.656578(12) 0.744918(16) 0.01620(5) Uani 1 1 d . . .
P1 P 0.71202(6) 0.58436(3) 0.67638(4) 0.01034(11) Uani 1 1 d . . .
P2 P 0.76411(6) 0.70168(3) 0.52644(4) 0.00952(11) Uani 1 1 d . . .
C01 C 0.8111(2) 0.62247(11) 0.59244(16) 0.0100(4) Uani 1 1 d . . .
H01A H 0.8215 0.5869 0.5436 0.012 Uiso 1 1 calc R . .
H01B H 0.9005 0.6304 0.6286 0.012 Uiso 1 1 calc R . .
C1 C 0.7744(2) 0.49782(11) 0.70184(17) 0.0127(4) Uani 1 1 d . . .
H1 H 0.7475 0.4705 0.6420 0.015 Uiso 1 1 calc R . .
C2 C 0.7120(2) 0.64241(12) 0.77825(17) 0.0133(5) Uani 1 1 d . . .
H2 H 0.7093 0.6901 0.7517 0.016 Uiso 1 1 calc R . .
C3 C 0.8902(2) 0.76567(12) 0.56168(17) 0.0122(4) Uani 1 1 d . . .
H3 H 0.9771 0.7463 0.5489 0.015 Uiso 1 1 calc R . .
C4 C 0.7465(2) 0.68371(12) 0.39893(16) 0.0140(5) Uani 1 1 d . . .
H4 H 0.7198 0.7274 0.3642 0.017 Uiso 1 1 calc R . .
C11 C 0.7054(3) 0.46459(13) 0.78052(19) 0.0202(5) Uani 1 1 d . . .
H11A H 0.7298 0.4159 0.7865 0.030 Uiso 1 1 calc R . .
H11B H 0.6090 0.4687 0.7635 0.030 Uiso 1 1 calc R . .
H11C H 0.7332 0.4879 0.8420 0.030 Uiso 1 1 calc R . .
C12 C 0.9246(3) 0.49269(13) 0.72318(19) 0.0186(5) Uani 1 1 d . . .
H12A H 0.9555 0.5162 0.7839 0.028 Uiso 1 1 calc R . .
H12B H 0.9645 0.5143 0.6710 0.028 Uiso 1 1 calc R . .
H12C H 0.9508 0.4443 0.7284 0.028 Uiso 1 1 calc R . .
C21 C 0.5921(3) 0.63506(14) 0.8314(2) 0.0241(6) Uani 1 1 d . . .
H21A H 0.5904 0.5887 0.8583 0.036 Uiso 1 1 calc R . .
H21B H 0.5108 0.6429 0.7866 0.036 Uiso 1 1 calc R . .
H21C H 0.5980 0.6688 0.8836 0.036 Uiso 1 1 calc R . .
C22 C 0.8438(3) 0.63563(13) 0.84616(17) 0.0168(5) Uani 1 1 d . . .
H22A H 0.8512 0.6730 0.8934 0.025 Uiso 1 1 calc R . .
H22B H 0.9180 0.6382 0.8086 0.025 Uiso 1 1 calc R . .
H22C H 0.8461 0.5914 0.8797 0.025 Uiso 1 1 calc R . .
C31 C 0.8641(3) 0.83052(13) 0.50073(19) 0.0189(5) Uani 1 1 d . . .
H31A H 0.7813 0.8519 0.5139 0.028 Uiso 1 1 calc R . .
H31B H 0.8564 0.8184 0.4324 0.028 Uiso 1 1 calc R . .
H31C H 0.9377 0.8628 0.5168 0.028 Uiso 1 1 calc R . .
C32 C 0.9024(3) 0.78188(13) 0.66950(17) 0.0162(5) Uani 1 1 d . . .
H32A H 0.9714 0.8166 0.6861 0.024 Uiso 1 1 calc R . .
H32B H 0.9261 0.7400 0.7066 0.024 Uiso 1 1 calc R . .
H32C H 0.8174 0.7994 0.6847 0.024 Uiso 1 1 calc R . .
C41 C 0.8815(3) 0.66212(14) 0.37105(18) 0.0199(5) Uani 1 1 d . . .
H41A H 0.9079 0.6178 0.4009 0.030 Uiso 1 1 calc R . .
H41B H 0.9483 0.6969 0.3936 0.030 Uiso 1 1 calc R . .
H41C H 0.8743 0.6579 0.3009 0.030 Uiso 1 1 calc R . .
C42 C 0.6375(3) 0.63058(13) 0.36825(18) 0.0199(5) Uani 1 1 d . . .
H42A H 0.6276 0.6244 0.2983 0.030 Uiso 1 1 calc R . .
H42B H 0.5534 0.6467 0.3869 0.030 Uiso 1 1 calc R . .
H42C H 0.6619 0.5867 0.4000 0.030 Uiso 1 1 calc R . .
C99 C 0.2296(3) 0.48380(14) 0.8540(2) 0.0204(5) Uani 1 1 d . . .
H99A H 0.1963 0.4383 0.8300 0.024 Uiso 1 1 calc R . .
H99B H 0.2121 0.5170 0.8003 0.024 Uiso 1 1 calc R . .
Cl98 Cl 0.40143(7) 0.47882(4) 0.89206(7) 0.0407(2) Uani 1 1 d . . .
Cl99 Cl 0.14416(8) 0.50981(4) 0.94911(5) 0.03061(16) Uani 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
Se1 Br5 2.5457(3) . ?
Se1 Br4 2.5577(3) . ?
Se1 Br6 2.6117(3) . ?
Se1 Br3 2.6286(3) . ?
Br1 P1 2.1486(7) . ?
Br2 P2 2.1597(6) . ?
P1 C01 1.812(2) . ?
P1 C1 1.819(2) . ?
P1 C2 1.822(2) . ?
P2 C4 1.807(2) . ?
P2 C3 1.808(2) . ?
P2 C01 1.828(2) . ?
C1 C12 1.520(3) . ?
C1 C11 1.531(3) . ?
C2 C21 1.523(3) . ?
C2 C22 1.539(3) . ?
C3 C31 1.528(3) . ?
C3 C32 1.533(3) . ?
C4 C42 1.534(3) . ?
C4 C41 1.538(3) . ?
C99 Cl98 1.759(3) . ?
C99 Cl99 1.765(3) . ?

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
Br5 Se1 Br4 91.849(10) . . ?
Br5 Se1 Br6 90.620(10) . . ?
Br4 Se1 Br6 177.447(12) . . ?
Br5 Se1 Br3 177.386(13) . . ?
Br4 Se1 Br3 90.368(10) . . ?
Br6 Se1 Br3 87.180(10) . . ?
C01 P1 C1 107.25(11) . . ?
C01 P1 C2 108.43(11) . . ?
C1 P1 C2 117.31(11) . . ?
C01 P1 Br1 109.80(8) . . ?
C1 P1 Br1 103.74(8) . . ?
C2 P1 Br1 110.11(8) . . ?
C4 P2 C3 111.92(11) . . ?
C4 P2 C01 108.72(11) . . ?
C3 P2 C01 108.48(11) . . ?
C4 P2 Br2 107.63(8) . . ?
C3 P2 Br2 107.40(8) . . ?
C01 P2 Br2 112.74(8) . . ?
P1 C01 P2 122.99(13) . . ?
C12 C1 C11 112.3(2) . . ?
C12 C1 P1 114.44(17) . . ?
C11 C1 P1 110.52(17) . . ?
C21 C2 C22 112.2(2) . . ?
C21 C2 P1 114.40(17) . . ?
C22 C2 P1 109.73(16) . . ?
C31 C3 C32 111.47(19) . . ?
C31 C3 P2 110.78(17) . . ?
C32 C3 P2 111.63(16) . . ?
C42 C4 C41 112.4(2) . . ?
C42 C4 P2 112.14(17) . . ?
C41 C4 P2 109.59(17) . . ?
Cl98 C99 Cl99 111.05(15) . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        29.57
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         1.708
_refine_diff_density_min         -0.627
_refine_diff_density_rms         0.105


# end of cif file
####################################################################### 
# 
# 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_dwayne
_database_code_depnum_ccdc_archive 'CCDC 1494782'
_audit_update_record             
;
2016-07-19 deposited with the CCDC.
2018-02-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H22 Br12 P2 Se2'
_chemical_formula_weight         1501.21

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'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.7943 1.1372 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.6944(7)
_cell_length_b                   11.7111(8)
_cell_length_c                   17.8163(6)
_cell_angle_alpha                88.036(4)
_cell_angle_beta                 77.486(4)
_cell_angle_gamma                78.064(6)
_cell_volume                     1931.8(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    27150
_cell_measurement_theta_min      3.8150
_cell_measurement_theta_max      76.2310

_exptl_crystal_description       needle
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.02
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.581
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1380
_exptl_absorpt_coefficient_mu    17.871
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.32755
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'sealed X-ray tube'
_diffrn_source_type              'Nova (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur, Atlas, Nova'
_diffrn_measurement_method       'ω scan'
_diffrn_detector_area_resol_mean 10.3543
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            76257
_diffrn_reflns_av_R_equivalents  0.0726
_diffrn_reflns_av_sigmaI/netI    0.0326
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         3.86
_diffrn_reflns_theta_max         78.24
_reflns_number_total             8068
_reflns_number_gt                6895
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker XP'
_computing_publication_material  SHELXL-97

_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)+(0.0312P)²+5.7541P] 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_number_reflns         8068
_refine_ls_number_parameters     370
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0392
_refine_ls_R_factor_gt           0.0297
_refine_ls_wR_factor_ref         0.0733
_refine_ls_wR_factor_gt          0.0677
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_restrained_S_all      1.032
_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
Br1 Br 0.69029(6) 0.50071(4) 0.78523(3) 0.02751(11) Uani 1 1 d . . .
Br2 Br 0.64248(6) 0.51792(4) 0.58558(3) 0.02555(11) Uani 1 1 d . . .
Br3 Br 0.88341(5) 0.22347(4) 0.70111(2) 0.02116(10) Uani 1 1 d . . .
Br4 Br 1.23215(6) 0.11753(5) 0.57033(3) 0.02964(12) Uani 1 1 d . . .
Br5 Br 1.21878(5) 0.14783(4) 0.77867(3) 0.02264(10) Uani 1 1 d . . .
Br6 Br 1.38350(5) 0.33567(4) 0.63647(3) 0.02405(10) Uani 1 1 d . . .
Br7 Br 1.05197(5) 0.45622(4) 0.76558(3) 0.02357(10) Uani 1 1 d . . .
Br8 Br 1.05453(6) 0.41826(4) 0.56740(3) 0.02666(11) Uani 1 1 d . . .
Br9 Br 0.66814(6) 0.20666(4) 0.89876(3) 0.02474(11) Uani 1 1 d . . .
Br10 Br 0.98405(6) 0.16562(4) 0.97747(2) 0.02309(10) Uani 1 1 d . . .
Br11 Br 0.96678(5) -0.04719(4) 0.83233(2) 0.02089(10) Uani 1 1 d . . .
Br12 Br 1.00891(5) -0.26421(4) 0.81565(3) 0.02379(10) Uani 1 1 d . . .
Se1 Se 1.14220(5) 0.28604(4) 0.66482(2) 0.01758(10) Uani 1 1 d . . .
Se2 Se 0.92478(5) 0.18092(4) 0.85363(3) 0.01938(10) Uani 1 1 d . . .
P1 P 0.47354(13) 0.59824(10) 0.81763(6) 0.0187(2) Uani 1 1 d . . .
P2 P 0.48880(13) 0.66434(9) 0.64385(6) 0.0186(2) Uani 1 1 d . . .
C01 C 0.3937(5) 0.6113(4) 0.7335(2) 0.0200(9) Uani 1 1 d . . .
H01A H 0.2976 0.6636 0.7476 0.024 Uiso 1 1 calc R . .
H01B H 0.3774 0.5334 0.7227 0.024 Uiso 1 1 calc R . .
C11 C 0.3690(6) 0.5203(4) 0.8873(3) 0.0228(9) Uani 1 1 d . . .
C12 C 0.3078(6) 0.5698(4) 0.9602(3) 0.0269(10) Uani 1 1 d . . .
H12 H 0.3242 0.6433 0.9728 0.032 Uiso 1 1 calc R . .
C13 C 0.2225(7) 0.5102(5) 1.0141(3) 0.0315(12) Uani 1 1 d . . .
H13 H 0.1788 0.5436 1.0636 0.038 Uiso 1 1 calc R . .
C14 C 0.2015(7) 0.4014(5) 0.9952(3) 0.0331(12) Uani 1 1 d . . .
H14 H 0.1440 0.3605 1.0321 0.040 Uiso 1 1 calc R . .
C15 C 0.2641(7) 0.3526(5) 0.9229(3) 0.0310(11) Uani 1 1 d . . .
H15 H 0.2495 0.2782 0.9108 0.037 Uiso 1 1 calc R . .
C16 C 0.3476(6) 0.4108(4) 0.8682(3) 0.0273(10) Uani 1 1 d . . .
H16 H 0.3896 0.3774 0.8185 0.033 Uiso 1 1 calc R . .
C21 C 0.4739(5) 0.7389(4) 0.8523(2) 0.0199(9) Uani 1 1 d . . .
C22 C 0.3408(5) 0.8180(4) 0.8703(2) 0.0210(9) Uani 1 1 d . . .
H22 H 0.2557 0.7966 0.8623 0.025 Uiso 1 1 calc R . .
C23 C 0.3343(6) 0.9269(4) 0.8997(2) 0.0236(10) Uani 1 1 d . . .
H23 H 0.2444 0.9805 0.9125 0.028 Uiso 1 1 calc R . .
C24 C 0.4596(6) 0.9579(4) 0.9105(3) 0.0280(11) Uani 1 1 d . . .
H24 H 0.4551 1.0336 0.9298 0.034 Uiso 1 1 calc R . .
C25 C 0.5908(6) 0.8800(5) 0.8935(3) 0.0298(11) Uani 1 1 d . . .
H25 H 0.6755 0.9019 0.9017 0.036 Uiso 1 1 calc R . .
C26 C 0.5989(6) 0.7696(5) 0.8643(3) 0.0272(10) Uani 1 1 d . . .
H26 H 0.6886 0.7157 0.8527 0.033 Uiso 1 1 calc R . .
C31 C 0.5827(5) 0.7745(4) 0.6592(2) 0.0211(9) Uani 1 1 d . . .
C32 C 0.5000(6) 0.8871(4) 0.6786(3) 0.0239(10) Uani 1 1 d . . .
H32 H 0.3989 0.9032 0.6813 0.029 Uiso 1 1 calc R . .
C33 C 0.5678(6) 0.9740(4) 0.6936(3) 0.0267(10) Uani 1 1 d . . .
H33 H 0.5129 1.0503 0.7073 0.032 Uiso 1 1 calc R . .
C34 C 0.7159(6) 0.9500(4) 0.6888(3) 0.0265(10) Uani 1 1 d . . .
H34 H 0.7620 1.0102 0.6989 0.032 Uiso 1 1 calc R . .
C35 C 0.7964(6) 0.8397(5) 0.6696(3) 0.0287(11) Uani 1 1 d . . .
H35 H 0.8975 0.8242 0.6668 0.034 Uiso 1 1 calc R . .
C36 C 0.7309(5) 0.7504(4) 0.6541(3) 0.0239(9) Uani 1 1 d . . .
H36 H 0.7867 0.6745 0.6404 0.029 Uiso 1 1 calc R . .
C41 C 0.3581(5) 0.7177(4) 0.5881(2) 0.0225(9) Uani 1 1 d . . .
C42 C 0.2324(5) 0.6731(4) 0.5979(3) 0.0244(10) Uani 1 1 d . . .
H42 H 0.2142 0.6151 0.6352 0.029 Uiso 1 1 calc R . .
C43 C 0.1345(6) 0.7154(4) 0.5519(3) 0.0259(10) Uani 1 1 d . . .
H43 H 0.0481 0.6865 0.5580 0.031 Uiso 1 1 calc R . .
C44 C 0.1621(6) 0.7996(5) 0.4970(3) 0.0290(11) Uani 1 1 d . . .
H44 H 0.0940 0.8288 0.4662 0.035 Uiso 1 1 calc R . .
C45 C 0.2881(6) 0.8410(4) 0.4870(3) 0.0289(11) Uani 1 1 d . . .
H45 H 0.3066 0.8979 0.4489 0.035 Uiso 1 1 calc R . .
C46 C 0.3880(6) 0.8008(4) 0.5319(3) 0.0241(10) Uani 1 1 d . . .
H46 H 0.4750 0.8290 0.5247 0.029 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.

 Bromine-bromine contacts:

      3.5911 (0.0007)  Br1 - Br3
      3.3783 (0.0008)  Br1 - Br7
      3.9542 (0.0007)  Br1 - Br9
      3.8678 (0.0008)  Br2 - Br8
      3.5746 (0.0008)  Br2 - Br6_$1
      3.7302 (0.0008)  Br2 - Br8_$2
      3.3410 (0.0007)  Br7 - Br12_$3
      3.2402 (0.0009)  Br8 - Br8_$2
      3.8969 (0.0010)  Br10 - Br10_$4
      3.7065 (0.0006)  Br10 - Br11_$4
      3.9189 (0.0007)  Br10 - Br12_$4

 Operators for generating equivalent atoms:

 $1   x-1, y, z
 $2   -x+2, -y+1, -z+1
 $3   x, y+1, z
 $4   -x+2, -y, -z+2
;

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
Br1 P1 2.1401(13) . ?
Br2 P2 2.1524(12) . ?
Br3 Se1 2.6970(7) . ?
Br3 Se2 2.8443(6) . ?
Br4 Se1 2.5235(7) . ?
Br5 Se1 2.6863(6) . ?
Br5 Se2 2.8259(7) . ?
Br6 Se1 2.4689(7) . ?
Br7 Se1 2.6084(6) . ?
Br8 Se1 2.4583(6) . ?
Br9 Se2 2.4015(7) . ?
Br10 Se2 2.3896(6) . ?
Br11 Br12 2.5069(7) . ?
Br11 Se2 2.6456(7) . ?
P1 C11 1.778(5) . ?
P1 C21 1.779(5) . ?
P1 C01 1.819(4) . ?
P2 C41 1.777(5) . ?
P2 C31 1.784(5) . ?
P2 C01 1.821(5) . ?
C11 C12 1.396(6) . ?
C11 C16 1.405(7) . ?
C12 C13 1.394(7) . ?
C13 C14 1.395(8) . ?
C14 C15 1.387(8) . ?
C15 C16 1.382(7) . ?
C21 C26 1.393(7) . ?
C21 C22 1.405(7) . ?
C22 C23 1.379(7) . ?
C23 C24 1.391(8) . ?
C24 C25 1.383(8) . ?
C25 C26 1.391(7) . ?
C31 C36 1.390(7) . ?
C31 C32 1.405(7) . ?
C32 C33 1.382(7) . ?
C33 C34 1.389(8) . ?
C34 C35 1.376(7) . ?
C35 C36 1.393(7) . ?
C41 C42 1.398(7) . ?
C41 C46 1.398(6) . ?
C42 C43 1.390(7) . ?
C43 C44 1.390(7) . ?
C44 C45 1.380(8) . ?
C45 C46 1.386(7) . ?

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
Se1 Br3 Se2 88.604(19) . . ?
Se1 Br5 Se2 89.20(2) . . ?
Br12 Br11 Se2 178.39(2) . . ?
Br8 Se1 Br6 93.90(2) . . ?
Br8 Se1 Br4 92.20(2) . . ?
Br6 Se1 Br4 90.51(2) . . ?
Br8 Se1 Br7 89.48(2) . . ?
Br6 Se1 Br7 89.36(2) . . ?
Br4 Se1 Br7 178.32(3) . . ?
Br8 Se1 Br5 175.63(3) . . ?
Br6 Se1 Br5 89.20(2) . . ?
Br4 Se1 Br5 90.84(2) . . ?
Br7 Se1 Br5 87.480(19) . . ?
Br8 Se1 Br3 89.11(2) . . ?
Br6 Se1 Br3 176.99(2) . . ?
Br4 Se1 Br3 89.18(2) . . ?
Br7 Se1 Br3 90.87(2) . . ?
Br5 Se1 Br3 87.81(2) . . ?
Br10 Se2 Br9 96.53(2) . . ?
Br10 Se2 Br11 94.62(2) . . ?
Br9 Se2 Br11 94.74(2) . . ?
Br10 Se2 Br5 91.83(2) . . ?
Br9 Se2 Br5 171.54(2) . . ?
Br11 Se2 Br5 83.31(2) . . ?
Br10 Se2 Br3 171.21(3) . . ?
Br9 Se2 Br3 89.48(2) . . ?
Br11 Se2 Br3 91.252(19) . . ?
Br5 Se2 Br3 82.353(19) . . ?
C11 P1 C21 111.7(2) . . ?
C11 P1 C01 106.7(2) . . ?
C21 P1 C01 110.3(2) . . ?
C11 P1 Br1 109.96(16) . . ?
C21 P1 Br1 109.81(17) . . ?
C01 P1 Br1 108.21(15) . . ?
C41 P2 C31 111.2(2) . . ?
C41 P2 C01 107.0(2) . . ?
C31 P2 C01 112.5(2) . . ?
C41 P2 Br2 109.65(15) . . ?
C31 P2 Br2 108.88(17) . . ?
C01 P2 Br2 107.52(15) . . ?
P1 C01 P2 119.6(3) . . ?
C12 C11 C16 121.0(5) . . ?
C12 C11 P1 119.2(4) . . ?
C16 C11 P1 119.8(4) . . ?
C13 C12 C11 119.2(5) . . ?
C12 C13 C14 119.8(5) . . ?
C15 C14 C13 120.3(5) . . ?
C16 C15 C14 120.9(5) . . ?
C15 C16 C11 118.7(5) . . ?
C26 C21 C22 120.3(4) . . ?
C26 C21 P1 122.3(4) . . ?
C22 C21 P1 117.3(4) . . ?
C23 C22 C21 119.7(5) . . ?
C22 C23 C24 119.8(5) . . ?
C25 C24 C23 120.8(5) . . ?
C24 C25 C26 120.0(5) . . ?
C25 C26 C21 119.4(5) . . ?
C36 C31 C32 120.8(5) . . ?
C36 C31 P2 121.9(4) . . ?
C32 C31 P2 117.3(4) . . ?
C33 C32 C31 119.1(5) . . ?
C32 C33 C34 120.1(5) . . ?
C35 C34 C33 120.5(5) . . ?
C34 C35 C36 120.6(5) . . ?
C31 C36 C35 118.9(5) . . ?
C42 C41 C46 121.2(4) . . ?
C42 C41 P2 120.5(4) . . ?
C46 C41 P2 118.2(4) . . ?
C43 C42 C41 118.6(5) . . ?
C44 C43 C42 120.4(5) . . ?
C45 C44 C43 120.1(5) . . ?
C44 C45 C46 120.9(5) . . ?
C45 C46 C41 118.6(5) . . ?

_diffrn_measured_fraction_theta_max 0.974
_diffrn_reflns_theta_full        75.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         1.071
_refine_diff_density_min         -0.976
_refine_diff_density_rms         0.150


# end of cif file
####################################################################### 
# 
# 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_roy
_database_code_depnum_ccdc_archive 'CCDC 1496349'
_audit_update_record             
;
2016-07-27 deposited with the CCDC.
2018-02-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C50 H46 Br6 O4 P4 Se2'
_chemical_formula_weight         1472.13

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'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.7943 1.1372 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 '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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'

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

_cell_length_a                   13.0635(3)
_cell_length_b                   9.5315(2)
_cell_length_c                   20.8476(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.676(2)
_cell_angle_gamma                90.00
_cell_volume                     2595.65(10)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    19818
_cell_measurement_theta_min      3.9410
_cell_measurement_theta_max      76.2620

_exptl_crystal_description       plate
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.884
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1432
_exptl_absorpt_coefficient_mu    8.712
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.59630
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'sealed X-ray tube'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur, Atlas, Nova'
_diffrn_measurement_method       'ω scan'
_diffrn_detector_area_resol_mean 10.3543
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            51628
_diffrn_reflns_av_R_equivalents  0.0682
_diffrn_reflns_av_sigmaI/netI    0.0300
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         3.97
_diffrn_reflns_theta_max         76.46
_reflns_number_total             5421
_reflns_number_gt                4616
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker XP'
_computing_publication_material  SHELXL-97

_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.

 The OH hydrogen was refined freely, although its position is ambiguous.
;

_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)+(0.0255P)²+2.4300P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         5421
_refine_ls_number_parameters     302
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0367
_refine_ls_R_factor_gt           0.0263
_refine_ls_wR_factor_ref         0.0617
_refine_ls_wR_factor_gt          0.0569
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_restrained_S_all      1.047
_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
Se1 Se 0.59667(2) 0.07875(3) 0.431137(14) 0.01651(7) Uani 1 1 d . . .
Br1 Br 0.62136(2) -0.02239(3) 0.554405(14) 0.01951(7) Uani 1 1 d . . .
Br2 Br 0.77894(2) 0.11486(3) 0.425512(15) 0.02179(8) Uani 1 1 d . . .
Br3 Br 0.57078(2) 0.15715(3) 0.319637(14) 0.02165(7) Uani 1 1 d . . .
P1 P 0.07889(5) 0.27750(7) 0.40215(3) 0.01488(14) Uani 1 1 d . . .
P2 P 0.20202(5) 0.44075(7) 0.50632(3) 0.01475(14) Uani 1 1 d . . .
O1 O -0.01680(15) 0.3672(2) 0.40768(10) 0.0202(4) Uani 1 1 d . . .
O2 O 0.11847(15) 0.5516(2) 0.50408(10) 0.0188(4) Uani 1 1 d . . .
H01 H 0.069(5) 0.589(6) 0.543(3) 0.09(2) Uiso 1 1 d . . .
C01 C 0.1557(2) 0.2750(3) 0.47469(13) 0.0161(5) Uani 1 1 d . . .
H01A H 0.2159 0.2145 0.4669 0.019 Uiso 1 1 calc R . .
H01B H 0.1150 0.2292 0.5085 0.019 Uiso 1 1 calc R . .
C11 C 0.0478(2) 0.0969(3) 0.38530(14) 0.0164(5) Uani 1 1 d . . .
C12 C 0.0729(2) -0.0138(3) 0.42693(14) 0.0201(6) Uani 1 1 d . . .
H12 H 0.1086 0.0041 0.4661 0.024 Uiso 1 1 calc R . .
C13 C 0.0449(2) -0.1503(3) 0.41027(16) 0.0247(6) Uani 1 1 d . . .
H13 H 0.0617 -0.2259 0.4382 0.030 Uiso 1 1 calc R . .
C14 C -0.0074(2) -0.1763(3) 0.35314(16) 0.0251(7) Uani 1 1 d . . .
H14 H -0.0271 -0.2695 0.3424 0.030 Uiso 1 1 calc R . .
C15 C -0.0311(2) -0.0665(3) 0.31154(16) 0.0249(6) Uani 1 1 d . . .
H15 H -0.0662 -0.0848 0.2722 0.030 Uiso 1 1 calc R . .
C16 C -0.0036(2) 0.0690(3) 0.32752(15) 0.0213(6) Uani 1 1 d . . .
H16 H -0.0198 0.1438 0.2991 0.026 Uiso 1 1 calc R . .
C21 C 0.1519(2) 0.3400(3) 0.33625(13) 0.0169(5) Uani 1 1 d . . .
C22 C 0.1050(2) 0.4263(3) 0.29058(14) 0.0193(6) Uani 1 1 d . . .
H22 H 0.0368 0.4582 0.2965 0.023 Uiso 1 1 calc R . .
C23 C 0.1589(2) 0.4654(3) 0.23619(15) 0.0246(6) Uani 1 1 d . . .
H23 H 0.1271 0.5229 0.2045 0.029 Uiso 1 1 calc R . .
C24 C 0.2589(2) 0.4206(3) 0.22822(15) 0.0253(7) Uani 1 1 d . . .
H24 H 0.2957 0.4479 0.1912 0.030 Uiso 1 1 calc R . .
C25 C 0.3055(2) 0.3360(3) 0.27415(15) 0.0235(6) Uani 1 1 d . . .
H25 H 0.3744 0.3071 0.2687 0.028 Uiso 1 1 calc R . .
C26 C 0.2523(2) 0.2932(3) 0.32803(14) 0.0199(6) Uani 1 1 d . . .
H26 H 0.2836 0.2330 0.3588 0.024 Uiso 1 1 calc R . .
C31 C 0.3075(2) 0.4948(3) 0.45880(14) 0.0174(6) Uani 1 1 d . . .
C32 C 0.3003(3) 0.6174(3) 0.42247(17) 0.0277(7) Uani 1 1 d . . .
H32 H 0.2413 0.6753 0.4248 0.033 Uiso 1 1 calc R . .
C33 C 0.3811(3) 0.6537(4) 0.38267(18) 0.0337(8) Uani 1 1 d . . .
H33 H 0.3770 0.7363 0.3573 0.040 Uiso 1 1 calc R . .
C34 C 0.4671(3) 0.5697(3) 0.38013(16) 0.0278(7) Uani 1 1 d . . .
H34 H 0.5213 0.5943 0.3523 0.033 Uiso 1 1 calc R . .
C35 C 0.4753(2) 0.4498(3) 0.41760(15) 0.0219(6) Uani 1 1 d . . .
H35 H 0.5354 0.3938 0.4162 0.026 Uiso 1 1 calc R . .
C36 C 0.3952(2) 0.4123(3) 0.45718(14) 0.0201(6) Uani 1 1 d . . .
H36 H 0.4003 0.3305 0.4831 0.024 Uiso 1 1 calc R . .
C41 C 0.2415(2) 0.3983(3) 0.58666(13) 0.0162(5) Uani 1 1 d . . .
C42 C 0.2350(2) 0.5019(3) 0.63425(14) 0.0198(6) Uani 1 1 d . . .
H42 H 0.2150 0.5948 0.6234 0.024 Uiso 1 1 calc R . .
C43 C 0.2583(2) 0.4672(3) 0.69707(15) 0.0227(6) Uani 1 1 d . . .
H43 H 0.2523 0.5362 0.7297 0.027 Uiso 1 1 calc R . .
C44 C 0.2905(2) 0.3324(3) 0.71323(14) 0.0209(6) Uani 1 1 d . . .
H44 H 0.3052 0.3094 0.7567 0.025 Uiso 1 1 calc R . .
C45 C 0.3011(2) 0.2316(3) 0.66569(14) 0.0212(6) Uani 1 1 d . . .
H45 H 0.3249 0.1403 0.6764 0.025 Uiso 1 1 calc R . .
C46 C 0.2767(2) 0.2646(3) 0.60253(14) 0.0187(6) Uani 1 1 d . . .
H46 H 0.2841 0.1958 0.5700 0.022 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
Se1 Br2 2.4099(4) . ?
Se1 Br3 2.4612(4) . ?
Se1 Br1 2.7600(4) . ?
Se1 Br1 2.9176(4) 3_656 ?
Br1 Se1 2.9176(4) 3_656 ?
P1 O1 1.520(2) . ?
P1 C21 1.784(3) . ?
P1 C11 1.803(3) . ?
P1 C01 1.805(3) . ?
P2 O2 1.519(2) . ?
P2 C31 1.782(3) . ?
P2 C41 1.793(3) . ?
P2 C01 1.813(3) . ?
C11 C16 1.398(4) . ?
C11 C12 1.402(4) . ?
C12 C13 1.394(4) . ?
C13 C14 1.388(5) . ?
C14 C15 1.392(5) . ?
C15 C16 1.380(4) . ?
C21 C22 1.395(4) . ?
C21 C26 1.397(4) . ?
C22 C23 1.393(4) . ?
C23 C24 1.386(5) . ?
C24 C25 1.387(4) . ?
C25 C26 1.390(4) . ?
C31 C36 1.391(4) . ?
C31 C32 1.395(4) . ?
C32 C33 1.394(5) . ?
C33 C34 1.380(5) . ?
C34 C35 1.387(5) . ?
C35 C36 1.387(4) . ?
C41 C46 1.393(4) . ?
C41 C42 1.404(4) . ?
C42 C43 1.381(4) . ?
C43 C44 1.392(4) . ?
C44 C45 1.388(4) . ?
C45 C46 1.387(4) . ?

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
Br2 Se1 Br3 92.035(14) . . ?
Br2 Se1 Br1 89.458(13) . . ?
Br3 Se1 Br1 177.035(16) . . ?
Br2 Se1 Br1 176.024(16) . 3_656 ?
Br3 Se1 Br1 91.721(13) . 3_656 ?
Br1 Se1 Br1 86.732(12) . 3_656 ?
Se1 Br1 Se1 93.268(12) . 3_656 ?
O1 P1 C21 108.58(13) . . ?
O1 P1 C11 111.62(13) . . ?
C21 P1 C11 106.85(13) . . ?
O1 P1 C01 113.17(12) . . ?
C21 P1 C01 110.64(13) . . ?
C11 P1 C01 105.79(13) . . ?
O2 P2 C31 109.97(13) . . ?
O2 P2 C41 112.58(12) . . ?
C31 P2 C41 111.67(13) . . ?
O2 P2 C01 111.00(13) . . ?
C31 P2 C01 107.86(13) . . ?
C41 P2 C01 103.53(13) . . ?
P1 C01 P2 118.21(15) . . ?
C16 C11 C12 119.8(3) . . ?
C16 C11 P1 117.0(2) . . ?
C12 C11 P1 123.2(2) . . ?
C13 C12 C11 119.3(3) . . ?
C14 C13 C12 120.4(3) . . ?
C13 C14 C15 120.2(3) . . ?
C16 C15 C14 119.8(3) . . ?
C15 C16 C11 120.5(3) . . ?
C22 C21 C26 120.7(3) . . ?
C22 C21 P1 119.2(2) . . ?
C26 C21 P1 119.9(2) . . ?
C23 C22 C21 119.4(3) . . ?
C24 C23 C22 120.1(3) . . ?
C23 C24 C25 120.2(3) . . ?
C24 C25 C26 120.6(3) . . ?
C25 C26 C21 119.0(3) . . ?
C36 C31 C32 120.7(3) . . ?
C36 C31 P2 119.5(2) . . ?
C32 C31 P2 119.8(2) . . ?
C33 C32 C31 119.0(3) . . ?
C34 C33 C32 120.1(3) . . ?
C33 C34 C35 120.9(3) . . ?
C36 C35 C34 119.6(3) . . ?
C35 C36 C31 119.7(3) . . ?
C46 C41 C42 119.9(3) . . ?
C46 C41 P2 121.3(2) . . ?
C42 C41 P2 118.9(2) . . ?
C43 C42 C41 119.1(3) . . ?
C42 C43 C44 120.9(3) . . ?
C45 C44 C43 119.9(3) . . ?
C46 C45 C44 119.8(3) . . ?
C45 C46 C41 120.3(3) . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        75.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         1.949
_refine_diff_density_min         -0.525
_refine_diff_density_rms         0.091


# start Validation Reply Form
_vrf_PLAT431_roy                 
;
PROBLEM: Short Inter HL..A Contact Br1 .. Se1 .. 2.92 Ang.
RESPONSE: This is a genuine short contact or long bond.
;
# end Validation Reply Form

# end of cif file
####################################################################### 
# 
# 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_tobi
_database_code_depnum_ccdc_archive 'CCDC 1574229'
_audit_update_record             
;
2017-09-13 deposited with the CCDC.
2018-02-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H31 Br4 P2 Se'
_chemical_formula_weight         659.93

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'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.7943 1.1372 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 '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/n'

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

_cell_length_a                   7.4264(2)
_cell_length_b                   28.7031(5)
_cell_length_c                   10.8682(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 96.958(2)
_cell_angle_gamma                90.00
_cell_volume                     2299.61(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    38831
_cell_measurement_theta_min      4.3500
_cell_measurement_theta_max      75.8050

_exptl_crystal_description       needle
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.906
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1276
_exptl_absorpt_coefficient_mu    11.609
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.33881
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43c (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur, Atlas, Nova'
_diffrn_measurement_method       'ω scan'
_diffrn_detector_area_resol_mean 10.3543
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            120978
_diffrn_reflns_av_R_equivalents  0.0937
_diffrn_reflns_av_sigmaI/netI    0.0214
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -36
_diffrn_reflns_limit_k_max       36
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         4.38
_diffrn_reflns_theta_max         76.29
_reflns_number_total             4819
_reflns_number_gt                4379
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro 1.171.38.43c (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43c (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43c (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    SHELXL-97
_computing_publication_material  'Bruker XP'

_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.

 The isopropyl group C3/C31/C32 is disordered and was refined isotropically
 on two split positions. Appropriate restraints were employed, but the
 dimensions of disordered groups should be interpreted with caution.
;

_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)+(0.0406P)²+9.8839P] 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_number_reflns         4819
_refine_ls_number_parameters     194
_refine_ls_number_restraints     13
_refine_ls_R_factor_all          0.0482
_refine_ls_R_factor_gt           0.0432
_refine_ls_wR_factor_ref         0.1048
_refine_ls_wR_factor_gt          0.1015
_refine_ls_goodness_of_fit_ref   1.073
_refine_ls_restrained_S_all      1.072
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.37034(16) 0.10078(4) 0.17193(12) 0.0328(3) Uani 1 1 d . . .
Se1 Se 0.20464(7) 0.034710(17) 0.14445(6) 0.03766(14) Uani 1 1 d . . .
Br1 Br 0.29513(9) 0.00807(2) 0.36712(7) 0.05906(19) Uani 1 1 d . . .
Br2 Br 0.10430(7) 0.051909(17) -0.08964(5) 0.04007(14) Uani 1 1 d . . .
Br3 Br 0.38778(8) 0.09021(2) 0.64795(6) 0.05228(17) Uani 1 1 d . A .
Br4 Br 0.77800(7) 0.204508(18) 0.32725(5) 0.04011(14) Uani 1 1 d . . .
C01 C 0.3870(6) 0.12154(16) 0.3302(5) 0.0357(10) Uani 1 1 d . . .
H01A H 0.4638 0.0994 0.3833 0.043 Uiso 1 1 calc R . .
H01B H 0.4509 0.1519 0.3345 0.043 Uiso 1 1 calc R . .
C02 C 0.2077(6) 0.12780(16) 0.3856(4) 0.0316(9) Uani 1 1 d . A .
H02A H 0.1401 0.0980 0.3789 0.038 Uiso 1 1 calc R . .
H02B H 0.1329 0.1514 0.3367 0.038 Uiso 1 1 calc R . .
C1 C 0.2711(7) 0.14634(16) 0.0667(5) 0.0389(11) Uani 1 1 d . . .
H1 H 0.2757 0.1347 -0.0196 0.047 Uiso 1 1 calc R . .
C12 C 0.3838(10) 0.19108(19) 0.0800(6) 0.0574(16) Uani 1 1 d . . .
H12A H 0.3365 0.2133 0.0156 0.086 Uiso 1 1 calc R . .
H12B H 0.5106 0.1838 0.0711 0.086 Uiso 1 1 calc R . .
H12C H 0.3766 0.2048 0.1619 0.086 Uiso 1 1 calc R . .
C11 C 0.0704(8) 0.15560(19) 0.0799(5) 0.0436(12) Uani 1 1 d . . .
H11A H 0.0618 0.1747 0.1537 0.065 Uiso 1 1 calc R . .
H11B H 0.0079 0.1259 0.0882 0.065 Uiso 1 1 calc R . .
H11C H 0.0135 0.1721 0.0063 0.065 Uiso 1 1 calc R . .
C2 C 0.6045(7) 0.09091(19) 0.1433(6) 0.0477(13) Uani 1 1 d . . .
H2 H 0.6734 0.1203 0.1647 0.057 Uiso 1 1 calc R . .
C22 C 0.6146(9) 0.0810(3) 0.0057(7) 0.071(2) Uani 1 1 d . . .
H22A H 0.7413 0.0761 -0.0078 0.106 Uiso 1 1 calc R . .
H22B H 0.5650 0.1075 -0.0440 0.106 Uiso 1 1 calc R . .
H22C H 0.5439 0.0530 -0.0192 0.106 Uiso 1 1 calc R . .
C21 C 0.6938(8) 0.0523(2) 0.2269(8) 0.067(2) Uani 1 1 d . . .
H21A H 0.6284 0.0230 0.2087 0.100 Uiso 1 1 calc R . .
H21B H 0.6899 0.0607 0.3139 0.100 Uiso 1 1 calc R . .
H21C H 0.8203 0.0485 0.2115 0.100 Uiso 1 1 calc R . .
P2 P 0.24078(17) 0.14572(4) 0.54607(11) 0.0361(3) Uani 1 1 d D . .
C3 C 0.4115(12) 0.1915(3) 0.5497(8) 0.033(2) Uiso 0.527(13) 1 d PDU A 1
H3 H 0.5036 0.1818 0.4948 0.040 Uiso 0.527(13) 1 calc PR A 1
C31 C 0.3116(18) 0.2345(4) 0.4913(12) 0.042(3) Uiso 0.527(13) 1 d PDU A 1
H31A H 0.2503 0.2264 0.4091 0.063 Uiso 0.527(13) 1 calc PR A 1
H31B H 0.3991 0.2595 0.4833 0.063 Uiso 0.527(13) 1 calc PR A 1
H31C H 0.2217 0.2450 0.5442 0.063 Uiso 0.527(13) 1 calc PR A 1
C32 C 0.5110(13) 0.2014(3) 0.6788(9) 0.040(3) Uiso 0.527(13) 1 d PDU A 1
H32A H 0.5735 0.1731 0.7114 0.059 Uiso 0.527(13) 1 calc PR A 1
H32B H 0.4232 0.2111 0.7342 0.059 Uiso 0.527(13) 1 calc PR A 1
H32C H 0.5998 0.2263 0.6733 0.059 Uiso 0.527(13) 1 calc PR A 1
C3' C 0.3329(12) 0.2057(3) 0.5789(8) 0.029(2) Uiso 0.473(13) 1 d PDU A 2
H3' H 0.2799 0.2179 0.6527 0.034 Uiso 0.473(13) 1 calc PR A 2
C31' C 0.2696(19) 0.2372(4) 0.4689(11) 0.035(3) Uiso 0.473(13) 1 d PDU A 2
H31D H 0.1369 0.2365 0.4531 0.053 Uiso 0.473(13) 1 calc PR A 2
H31E H 0.3211 0.2262 0.3954 0.053 Uiso 0.473(13) 1 calc PR A 2
H31F H 0.3101 0.2692 0.4878 0.053 Uiso 0.473(13) 1 calc PR A 2
C32' C 0.5391(13) 0.2049(4) 0.6106(11) 0.038(3) Uiso 0.473(13) 1 d PDU A 2
H32D H 0.5719 0.1847 0.6824 0.057 Uiso 0.473(13) 1 calc PR A 2
H32E H 0.5830 0.2366 0.6300 0.057 Uiso 0.473(13) 1 calc PR A 2
H32F H 0.5946 0.1930 0.5395 0.057 Uiso 0.473(13) 1 calc PR A 2
C4 C 0.0232(7) 0.15232(17) 0.5993(5) 0.0389(11) Uani 1 1 d . A .
C42 C 0.0369(10) 0.1696(2) 0.7331(5) 0.0582(17) Uani 1 1 d . . .
H42A H -0.0846 0.1709 0.7594 0.087 Uiso 1 1 calc R A .
H42B H 0.0912 0.2008 0.7385 0.087 Uiso 1 1 calc R . .
H42C H 0.1129 0.1482 0.7871 0.087 Uiso 1 1 calc R . .
C41 C -0.0861(7) 0.1071(2) 0.5819(5) 0.0435(12) Uani 1 1 d . . .
H41A H -0.0252 0.0827 0.6347 0.065 Uiso 1 1 calc R A .
H41B H -0.0948 0.0973 0.4949 0.065 Uiso 1 1 calc R . .
H41C H -0.2081 0.1122 0.6048 0.065 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
P1 C01 1.810(5) . ?
P1 C2 1.826(5) . ?
P1 C1 1.833(5) . ?
P1 Se1 2.2607(12) . ?
Se1 Br1 2.5492(9) . ?
Se1 Br2 2.6100(8) . ?
Br3 P2 2.1596(14) . ?
C01 C02 1.537(6) . ?
C02 P2 1.806(5) . ?
C1 C12 1.530(7) . ?
C1 C11 1.538(7) . ?
C2 C21 1.533(9) . ?
C2 C22 1.533(9) . ?
P2 C4 1.791(5) . ?
P2 C3 1.824(8) . ?
P2 C3' 1.871(8) . ?
C3 C32 1.531(10) . ?
C3 C31 1.536(11) . ?
C3' C31' 1.527(12) . ?
C3' C32' 1.528(11) . ?
C4 C42 1.528(7) . ?
C4 C41 1.531(7) . ?

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
C01 P1 C2 104.8(2) . . ?
C01 P1 C1 109.5(2) . . ?
C2 P1 C1 108.9(3) . . ?
C01 P1 Se1 112.04(15) . . ?
C2 P1 Se1 111.21(18) . . ?
C1 P1 Se1 110.16(17) . . ?
P1 Se1 Br1 92.84(4) . . ?
P1 Se1 Br2 93.25(4) . . ?
Br1 Se1 Br2 173.40(3) . . ?
C02 C01 P1 116.6(3) . . ?
C01 C02 P2 112.9(3) . . ?
C12 C1 C11 111.8(5) . . ?
C12 C1 P1 111.4(4) . . ?
C11 C1 P1 112.7(3) . . ?
C21 C2 C22 112.0(5) . . ?
C21 C2 P1 111.3(4) . . ?
C22 C2 P1 110.8(4) . . ?
C4 P2 C02 108.6(2) . . ?
C4 P2 C3 124.7(4) . . ?
C02 P2 C3 103.8(3) . . ?
C4 P2 C3' 99.5(3) . . ?
C02 P2 C3' 116.7(3) . . ?
C3 P2 C3' 25.2(3) . . ?
C4 P2 Br3 109.41(17) . . ?
C02 P2 Br3 106.62(16) . . ?
C3 P2 Br3 102.3(3) . . ?
C3' P2 Br3 115.5(3) . . ?
C32 C3 C31 112.7(8) . . ?
C32 C3 P2 114.2(6) . . ?
C31 C3 P2 105.7(7) . . ?
C31' C3' C32' 113.0(9) . . ?
C31' C3' P2 109.0(7) . . ?
C32' C3' P2 111.3(6) . . ?
C42 C4 C41 111.5(5) . . ?
C42 C4 P2 112.5(4) . . ?
C41 C4 P2 110.8(3) . . ?

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
C01 P1 Se1 Br1 -30.01(17) . . . . ?
C2 P1 Se1 Br1 87.0(2) . . . . ?
C1 P1 Se1 Br1 -152.22(18) . . . . ?
C01 P1 Se1 Br2 152.55(16) . . . . ?
C2 P1 Se1 Br2 -90.5(2) . . . . ?
C1 P1 Se1 Br2 30.34(18) . . . . ?
C2 P1 C01 C02 -173.5(4) . . . . ?
C1 P1 C01 C02 69.8(4) . . . . ?
Se1 P1 C01 C02 -52.7(4) . . . . ?
P1 C01 C02 P2 177.0(2) . . . . ?
C01 P1 C1 C12 58.2(5) . . . . ?
C2 P1 C1 C12 -55.9(5) . . . . ?
Se1 P1 C1 C12 -178.1(4) . . . . ?
C01 P1 C1 C11 -68.4(4) . . . . ?
C2 P1 C1 C11 177.4(4) . . . . ?
Se1 P1 C1 C11 55.2(4) . . . . ?
C01 P1 C2 C21 64.1(5) . . . . ?
C1 P1 C2 C21 -178.7(4) . . . . ?
Se1 P1 C2 C21 -57.2(5) . . . . ?
C01 P1 C2 C22 -170.5(4) . . . . ?
C1 P1 C2 C22 -53.4(5) . . . . ?
Se1 P1 C2 C22 68.2(5) . . . . ?
C01 C02 P2 C4 179.5(3) . . . . ?
C01 C02 P2 C3 44.9(4) . . . . ?
C01 C02 P2 C3' 68.1(5) . . . . ?
C01 C02 P2 Br3 -62.7(3) . . . . ?
C4 P2 C3 C32 74.9(8) . . . . ?
C02 P2 C3 C32 -160.3(7) . . . . ?
C3' P2 C3 C32 75.3(10) . . . . ?
Br3 P2 C3 C32 -49.5(7) . . . . ?
C4 P2 C3 C31 -49.5(8) . . . . ?
C02 P2 C3 C31 75.3(7) . . . . ?
C3' P2 C3 C31 -49.1(9) . . . . ?
Br3 P2 C3 C31 -173.9(6) . . . . ?
C4 P2 C3' C31' -85.8(7) . . . . ?
C02 P2 C3' C31' 30.7(8) . . . . ?
C3 P2 C3' C31' 94.5(11) . . . . ?
Br3 P2 C3' C31' 157.2(6) . . . . ?
C4 P2 C3' C32' 149.0(7) . . . . ?
C02 P2 C3' C32' -94.5(7) . . . . ?
C3 P2 C3' C32' -30.8(8) . . . . ?
Br3 P2 C3' C32' 32.0(8) . . . . ?
C02 P2 C4 C42 -177.4(4) . . . . ?
C3 P2 C4 C42 -54.8(5) . . . . ?
C3' P2 C4 C42 -54.9(5) . . . . ?
Br3 P2 C4 C42 66.5(4) . . . . ?
C02 P2 C4 C41 57.0(4) . . . . ?
C3 P2 C4 C41 179.6(4) . . . . ?
C3' P2 C4 C41 179.5(4) . . . . ?
Br3 P2 C4 C41 -59.1(4) . . . . ?

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
C01 H01B Br4 0.99 2.87 3.758(5) 149.7 .
C2 H2 Br4 1.00 3.04 3.958(5) 153.5 .
C3 H3 Br4 1.00 2.97 3.871(9) 151.0 .
C32 H32B Br4 0.98 2.88 3.684(10) 139.3 4_566

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        75.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.736
_refine_diff_density_min         -1.761
_refine_diff_density_rms         0.115

####################################################################### 
# 
# 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_ella
_database_code_depnum_ccdc_archive 'CCDC 1494781'
_audit_update_record             
;
2016-07-19 deposited with the CCDC.
2018-02-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H30 I4 P2 Se2'
_chemical_formula_weight         913.83

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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 '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 n'

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

_cell_length_a                   8.6379(4)
_cell_length_b                   14.2975(5)
_cell_length_c                   10.2018(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 95.358(4)
_cell_angle_gamma                90.00
_cell_volume                     1254.43(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    16335
_cell_measurement_theta_min      2.4480
_cell_measurement_theta_max      30.7480

_exptl_crystal_description       plate
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.419
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             836
_exptl_absorpt_coefficient_mu    7.992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.55113
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           'Mo K\a'
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur, Eos'
_diffrn_measurement_method       'ω scan'
_diffrn_detector_area_resol_mean 16.1419
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            39452
_diffrn_reflns_av_R_equivalents  0.0354
_diffrn_reflns_av_sigmaI/netI    0.0272
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.46
_diffrn_reflns_theta_max         30.97
_reflns_number_total             7359
_reflns_number_gt                7101
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker XP'
_computing_publication_material  SHELXL-97

_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)+(0.0140P)²+0.6444P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.020(6)
_refine_ls_number_reflns         7359
_refine_ls_number_parameters     198
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0216
_refine_ls_R_factor_gt           0.0200
_refine_ls_wR_factor_ref         0.0393
_refine_ls_wR_factor_gt          0.0386
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_restrained_S_all      1.035
_refine_ls_shift/su_max          0.002
_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
I1 I 0.15291(3) 0.013332(15) 0.27147(2) 0.02034(5) Uani 1 1 d . . .
I2 I -0.02402(2) 0.165558(15) 0.567554(19) 0.01963(5) Uani 1 1 d . . .
I3 I -0.06242(3) 0.246974(16) 0.82273(2) 0.01606(4) Uani 1 1 d . . .
I4 I -0.10100(3) 0.336826(17) 1.07523(2) 0.02434(5) Uani 1 1 d . . .
Se1 Se 0.23970(4) 0.19342(2) 0.32467(3) 0.01567(6) Uani 1 1 d . . .
Se2 Se 0.29314(4) 0.37988(2) 0.37669(3) 0.01949(7) Uani 1 1 d . . .
P1 P 0.46723(9) 0.18726(6) 0.23714(7) 0.01170(15) Uani 1 1 d . . .
P2 P 0.53577(10) 0.35655(6) 0.43151(8) 0.01334(15) Uani 1 1 d . . .
C01 C 0.6070(4) 0.2644(2) 0.3284(3) 0.0126(6) Uani 1 1 d . . .
H01A H 0.6695 0.2948 0.2638 0.015 Uiso 1 1 calc R . .
H01B H 0.6789 0.2247 0.3854 0.015 Uiso 1 1 calc R . .
C1 C 0.5527(4) 0.0705(2) 0.2495(3) 0.0163(6) Uani 1 1 d . . .
H1 H 0.4791 0.0271 0.1982 0.020 Uiso 1 1 calc R . .
C2 C 0.4500(4) 0.2201(2) 0.0629(3) 0.0176(6) Uani 1 1 d . . .
H2 H 0.5567 0.2198 0.0323 0.021 Uiso 1 1 calc R . .
C3 C 0.6541(4) 0.4601(2) 0.4074(3) 0.0183(6) Uani 1 1 d . . .
H3 H 0.6253 0.5084 0.4716 0.022 Uiso 1 1 calc R . .
C4 C 0.5818(4) 0.3194(2) 0.6028(3) 0.0174(6) Uani 1 1 d . . .
H4 H 0.6937 0.3005 0.6129 0.021 Uiso 1 1 calc R . .
C11 C 0.7059(4) 0.0683(2) 0.1855(4) 0.0234(7) Uani 1 1 d . . .
H11A H 0.7517 0.0057 0.1950 0.035 Uiso 1 1 calc R . .
H11B H 0.7780 0.1142 0.2288 0.035 Uiso 1 1 calc R . .
H11C H 0.6863 0.0838 0.0918 0.035 Uiso 1 1 calc R . .
C12 C 0.5722(4) 0.0350(2) 0.3914(3) 0.0224(7) Uani 1 1 d . . .
H12A H 0.6548 0.0706 0.4415 0.034 Uiso 1 1 calc R . .
H12B H 0.6000 -0.0314 0.3921 0.034 Uiso 1 1 calc R . .
H12C H 0.4744 0.0432 0.4316 0.034 Uiso 1 1 calc R . .
C21 C 0.3529(4) 0.1464(3) -0.0159(3) 0.0209(7) Uani 1 1 d . . .
H21A H 0.3428 0.1636 -0.1093 0.031 Uiso 1 1 calc R . .
H21B H 0.2494 0.1430 0.0159 0.031 Uiso 1 1 calc R . .
H21C H 0.4040 0.0854 -0.0048 0.031 Uiso 1 1 calc R . .
C22 C 0.3814(4) 0.3180(2) 0.0389(3) 0.0228(7) Uani 1 1 d . . .
H22A H 0.2799 0.3214 0.0742 0.034 Uiso 1 1 calc R . .
H22B H 0.3689 0.3307 -0.0559 0.034 Uiso 1 1 calc R . .
H22C H 0.4515 0.3645 0.0830 0.034 Uiso 1 1 calc R . .
C31 C 0.8288(4) 0.4382(2) 0.4402(3) 0.0210(7) Uani 1 1 d . . .
H31A H 0.8906 0.4932 0.4213 0.031 Uiso 1 1 calc R . .
H31B H 0.8582 0.3854 0.3866 0.031 Uiso 1 1 calc R . .
H31C H 0.8482 0.4222 0.5337 0.031 Uiso 1 1 calc R . .
C32 C 0.6204(4) 0.5019(2) 0.2693(4) 0.0236(8) Uani 1 1 d . . .
H32A H 0.6562 0.4586 0.2040 0.035 Uiso 1 1 calc R . .
H32B H 0.6751 0.5617 0.2647 0.035 Uiso 1 1 calc R . .
H32C H 0.5083 0.5121 0.2510 0.035 Uiso 1 1 calc R . .
C41 C 0.5631(5) 0.4012(3) 0.6975(3) 0.0249(8) Uani 1 1 d . . .
H41A H 0.5826 0.3792 0.7885 0.037 Uiso 1 1 calc R . .
H41B H 0.4572 0.4260 0.6831 0.037 Uiso 1 1 calc R . .
H41C H 0.6378 0.4505 0.6813 0.037 Uiso 1 1 calc R . .
C42 C 0.4866(5) 0.2347(3) 0.6377(3) 0.0255(8) Uani 1 1 d . . .
H42A H 0.3768 0.2524 0.6361 0.038 Uiso 1 1 calc R . .
H42B H 0.5238 0.2126 0.7260 0.038 Uiso 1 1 calc R . .
H42C H 0.4979 0.1848 0.5736 0.038 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
I1 Se1 2.7222(4) . ?
I2 I3 2.8989(3) . ?
I3 I4 2.9252(3) . ?
Se1 P1 2.2351(8) . ?
Se1 Se2 2.7487(5) . ?
Se2 P2 2.1442(9) . ?
P1 C1 1.825(3) . ?
P1 C01 1.825(3) . ?
P1 C2 1.831(3) . ?
P2 C01 1.828(3) . ?
P2 C3 1.829(3) . ?
P2 C4 1.834(3) . ?
C1 C12 1.528(4) . ?
C1 C11 1.530(5) . ?
C2 C21 1.528(5) . ?
C2 C22 1.530(5) . ?
C3 C32 1.533(5) . ?
C3 C31 1.546(5) . ?
C4 C42 1.525(5) . ?
C4 C41 1.534(5) . ?

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
I2 I3 I4 177.623(11) . . ?
P1 Se1 I1 96.84(2) . . ?
P1 Se1 Se2 88.70(2) . . ?
I1 Se1 Se2 173.712(16) . . ?
P2 Se2 Se1 92.41(3) . . ?
C1 P1 C01 105.90(14) . . ?
C1 P1 C2 107.29(15) . . ?
C01 P1 C2 109.24(15) . . ?
C1 P1 Se1 111.94(11) . . ?
C01 P1 Se1 109.69(10) . . ?
C2 P1 Se1 112.52(11) . . ?
C01 P2 C3 106.45(15) . . ?
C01 P2 C4 106.58(14) . . ?
C3 P2 C4 106.75(16) . . ?
C01 P2 Se2 109.59(10) . . ?
C3 P2 Se2 112.59(12) . . ?
C4 P2 Se2 114.42(12) . . ?
P1 C01 P2 119.13(17) . . ?
C12 C1 C11 112.0(3) . . ?
C12 C1 P1 112.1(2) . . ?
C11 C1 P1 110.4(2) . . ?
C21 C2 C22 111.1(3) . . ?
C21 C2 P1 108.9(2) . . ?
C22 C2 P1 112.7(2) . . ?
C32 C3 C31 112.1(3) . . ?
C32 C3 P2 112.3(2) . . ?
C31 C3 P2 110.7(2) . . ?
C42 C4 C41 111.5(3) . . ?
C42 C4 P2 112.3(2) . . ?
C41 C4 P2 110.7(2) . . ?

_diffrn_measured_fraction_theta_max 0.960
_diffrn_reflns_theta_full        30.00
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.688
_refine_diff_density_min         -0.652
_refine_diff_density_rms         0.108


# end of cif file
####################################################################### 
# 
# 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_miriam
_database_code_depnum_ccdc_archive 'CCDC 1496347'
_audit_update_record             
;
2016-07-27 deposited with the CCDC.
2018-02-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H62 Br4 O4 P4 Se2'
_chemical_formula_weight         1040.20

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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 2/c'

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

_cell_length_a                   29.346(2)
_cell_length_b                   13.8633(5)
_cell_length_c                   20.2475(8)
_cell_angle_alpha                90.00
_cell_angle_beta                 99.575(4)
_cell_angle_gamma                90.00
_cell_volume                     8122.5(7)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    13676
_cell_measurement_theta_min      2.6330
_cell_measurement_theta_max      30.3270

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.701
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             4144
_exptl_absorpt_coefficient_mu    5.942
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.78264
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur, Eos'
_diffrn_measurement_method       'ω scan'
_diffrn_detector_area_resol_mean 16.1419
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            104958
_diffrn_reflns_av_R_equivalents  0.0679
_diffrn_reflns_av_sigmaI/netI    0.0440
_diffrn_reflns_limit_h_min       -41
_diffrn_reflns_limit_h_max       39
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         2.28
_diffrn_reflns_theta_max         30.03
_reflns_number_total             11785
_reflns_number_gt                9137
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker XP'
_computing_publication_material  SHELXL-97

_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.

 The OH hydrogens were refined freely.

 Two isopropyl groups were disordered over two positions. Despite the use
 of suitable restraints, dimensions of disordered groups should be
 interpreted with caution.
;

_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)+(0.0232P)²+17.0964P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         11785
_refine_ls_number_parameters     408
_refine_ls_number_restraints     38
_refine_ls_R_factor_all          0.0580
_refine_ls_R_factor_gt           0.0353
_refine_ls_wR_factor_ref         0.0698
_refine_ls_wR_factor_gt          0.0642
_refine_ls_goodness_of_fit_ref   1.049
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.003
_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
Se1 Se 0.649297(9) 0.622328(19) 0.588392(13) 0.01497(6) Uani 1 1 d . . .
Se2 Se 0.592154(9) 0.630662(19) 0.651885(13) 0.01475(6) Uani 1 1 d . . .
Br1 Br 0.714289(10) 0.74464(2) 0.659840(14) 0.02252(7) Uani 1 1 d . . .
Br2 Br 0.613474(10) 0.506649(19) 0.499842(13) 0.02050(7) Uani 1 1 d . . .
Br3 Br 0.620027(11) 0.49682(2) 0.733434(15) 0.02613(7) Uani 1 1 d . . .
Br4 Br 0.540809(10) 0.78072(2) 0.590161(13) 0.01890(6) Uani 1 1 d . . .
P1 P 0.47742(2) 0.23340(5) 0.62991(3) 0.01116(13) Uani 1 1 d . . .
P2 P 0.37385(2) 0.16927(5) 0.59487(3) 0.01039(13) Uani 1 1 d . . .
P3 P 0.36687(2) -0.16107(5) 0.66340(3) 0.01172(13) Uani 1 1 d . . .
P4 P 0.26838(2) -0.25190(5) 0.61893(3) 0.01115(13) Uani 1 1 d . . .
O1 O 0.47135(6) 0.19894(13) 0.69965(9) 0.0154(4) Uani 1 1 d . . .
O2 O 0.39049(6) 0.07172(13) 0.62344(9) 0.0149(4) Uani 1 1 d . A .
O3 O 0.34516(6) -0.07301(13) 0.62521(9) 0.0153(4) Uani 1 1 d . B .
O4 O 0.27345(6) -0.21564(13) 0.54927(8) 0.0147(4) Uani 1 1 d . B .
C01 C 0.42164(9) 0.23990(17) 0.57564(12) 0.0116(5) Uani 1 1 d . A .
H01A H 0.4119 0.3083 0.5736 0.014 Uiso 1 1 calc R . .
H01B H 0.4264 0.2217 0.5300 0.014 Uiso 1 1 calc R . .
C02 C 0.32288(9) -0.24655(18) 0.67598(12) 0.0126(5) Uani 1 1 d . B .
H02A H 0.3156 -0.2349 0.7213 0.015 Uiso 1 1 calc R . .
H02B H 0.3370 -0.3115 0.6767 0.015 Uiso 1 1 calc R . .
C1 C 0.51274(10) 0.1517(2) 0.59054(14) 0.0186(6) Uani 1 1 d . . .
H1 H 0.5137 0.1758 0.5442 0.022 Uiso 1 1 calc R . .
C11 C 0.56236(10) 0.1507(2) 0.62939(17) 0.0291(7) Uani 1 1 d . . .
H11A H 0.5810 0.1051 0.6082 0.044 Uiso 1 1 calc R . .
H11B H 0.5620 0.1307 0.6757 0.044 Uiso 1 1 calc R . .
H11C H 0.5757 0.2154 0.6290 0.044 Uiso 1 1 calc R . .
C12 C 0.49234(10) 0.0499(2) 0.58510(15) 0.0239(6) Uani 1 1 d . . .
H12A H 0.4878 0.0279 0.6295 0.036 Uiso 1 1 calc R . .
H12B H 0.5136 0.0061 0.5675 0.036 Uiso 1 1 calc R . .
H12C H 0.4626 0.0506 0.5548 0.036 Uiso 1 1 calc R . .
C2 C 0.50300(9) 0.35228(19) 0.63387(13) 0.0162(5) Uani 1 1 d . . .
H2 H 0.5331 0.3480 0.6652 0.019 Uiso 1 1 calc R . .
C21 C 0.51384(11) 0.3868(2) 0.56611(15) 0.0256(7) Uani 1 1 d . . .
H21A H 0.5267 0.4521 0.5709 0.038 Uiso 1 1 calc R . .
H21B H 0.4854 0.3872 0.5330 0.038 Uiso 1 1 calc R . .
H21C H 0.5363 0.3431 0.5512 0.038 Uiso 1 1 calc R . .
C22 C 0.47293(10) 0.4252(2) 0.66423(14) 0.0206(6) Uani 1 1 d . . .
H22A H 0.4455 0.4407 0.6313 0.031 Uiso 1 1 calc R . .
H22B H 0.4907 0.4842 0.6765 0.031 Uiso 1 1 calc R . .
H22C H 0.4634 0.3973 0.7042 0.031 Uiso 1 1 calc R . .
C3 C 0.34154(16) 0.2330(3) 0.64954(18) 0.0148(8) Uani 0.785(7) 1 d PDU A 1
H3 H 0.3123 0.1960 0.6493 0.018 Uiso 0.785(7) 1 calc PR A 1
C31 C 0.36649(13) 0.2344(3) 0.72197(17) 0.0205(10) Uani 0.785(7) 1 d PD A 1
H31A H 0.3461 0.2618 0.7508 0.031 Uiso 0.785(7) 1 calc PR A 1
H31B H 0.3945 0.2738 0.7252 0.031 Uiso 0.785(7) 1 calc PR A 1
H31C H 0.3749 0.1684 0.7365 0.031 Uiso 0.785(7) 1 calc PR A 1
C32 C 0.3274(4) 0.3341(5) 0.6239(5) 0.0179(17) Uani 0.785(7) 1 d PDU A 1
H32A H 0.3546 0.3762 0.6302 0.027 Uiso 0.785(7) 1 calc PR A 1
H32B H 0.3043 0.3600 0.6489 0.027 Uiso 0.785(7) 1 calc PR A 1
H32C H 0.3143 0.3309 0.5762 0.027 Uiso 0.785(7) 1 calc PR A 1
C3' C 0.3589(5) 0.2460(9) 0.6629(6) 0.008(3) Uiso 0.215(7) 1 d PDU A 2
H3' H 0.3886 0.2713 0.6883 0.009 Uiso 0.215(7) 1 calc PR A 2
C31' C 0.3366(4) 0.1879(8) 0.7117(6) 0.015(3) Uiso 0.215(7) 1 d PD A 2
H31D H 0.3560 0.1319 0.7266 0.022 Uiso 0.215(7) 1 calc PR A 2
H31E H 0.3061 0.1659 0.6898 0.022 Uiso 0.215(7) 1 calc PR A 2
H31F H 0.3333 0.2281 0.7504 0.022 Uiso 0.215(7) 1 calc PR A 2
C32' C 0.3308(15) 0.333(2) 0.634(2) 0.019(8) Uiso 0.215(7) 1 d PDU A 2
H32D H 0.3473 0.3668 0.6029 0.029 Uiso 0.215(7) 1 calc PR A 2
H32E H 0.3264 0.3766 0.6707 0.029 Uiso 0.215(7) 1 calc PR A 2
H32F H 0.3006 0.3114 0.6107 0.029 Uiso 0.215(7) 1 calc PR A 2
C4 C 0.33500(9) 0.1558(2) 0.51617(14) 0.0198(6) Uani 1 1 d . A .
H4 H 0.3323 0.2199 0.4932 0.024 Uiso 1 1 calc R . .
C41 C 0.35464(12) 0.0846(2) 0.47133(15) 0.0315(8) Uani 1 1 d . . .
H41A H 0.3336 0.0793 0.4285 0.047 Uiso 1 1 calc R A .
H41B H 0.3581 0.0213 0.4931 0.047 Uiso 1 1 calc R . .
H41C H 0.3849 0.1073 0.4634 0.047 Uiso 1 1 calc R . .
C42 C 0.28644(10) 0.1243(2) 0.52570(18) 0.0332(8) Uani 1 1 d . . .
H42A H 0.2880 0.0601 0.5463 0.050 Uiso 1 1 calc R A .
H42B H 0.2662 0.1221 0.4821 0.050 Uiso 1 1 calc R . .
H42C H 0.2741 0.1705 0.5549 0.050 Uiso 1 1 calc R . .
C5 C 0.25108(10) -0.37743(19) 0.61378(14) 0.0183(6) Uani 1 1 d . B .
H5 H 0.2208 -0.3810 0.5829 0.022 Uiso 1 1 calc R . .
C51 C 0.28598(11) -0.4361(2) 0.58169(16) 0.0263(7) Uani 1 1 d . . .
H51A H 0.3157 -0.4377 0.6121 0.039 Uiso 1 1 calc R B .
H51B H 0.2901 -0.4060 0.5393 0.039 Uiso 1 1 calc R . .
H51C H 0.2745 -0.5020 0.5732 0.039 Uiso 1 1 calc R . .
C52 C 0.24385(12) -0.4200(2) 0.68081(15) 0.0292(7) Uani 1 1 d . . .
H52A H 0.2346 -0.4878 0.6746 0.044 Uiso 1 1 calc R B .
H52B H 0.2196 -0.3838 0.6980 0.044 Uiso 1 1 calc R . .
H52C H 0.2727 -0.4159 0.7129 0.044 Uiso 1 1 calc R . .
C6 C 0.22674(9) -0.1824(2) 0.65493(13) 0.0168(6) Uani 1 1 d . B .
H6 H 0.2268 -0.2059 0.7016 0.020 Uiso 1 1 calc R . .
C61 C 0.23935(10) -0.0745(2) 0.65823(16) 0.0260(7) Uani 1 1 d . . .
H61A H 0.2407 -0.0507 0.6130 0.039 Uiso 1 1 calc R B .
H61B H 0.2695 -0.0658 0.6866 0.039 Uiso 1 1 calc R . .
H61C H 0.2159 -0.0384 0.6772 0.039 Uiso 1 1 calc R . .
C62 C 0.17837(10) -0.1971(2) 0.61507(15) 0.0259(7) Uani 1 1 d . . .
H62A H 0.1563 -0.1573 0.6343 0.039 Uiso 1 1 calc R B .
H62B H 0.1697 -0.2652 0.6169 0.039 Uiso 1 1 calc R . .
H62C H 0.1781 -0.1782 0.5683 0.039 Uiso 1 1 calc R . .
C7 C 0.39550(10) -0.1283(2) 0.74670(14) 0.0257(7) Uani 1 1 d . B .
H7 H 0.4023 -0.1891 0.7731 0.031 Uiso 1 1 calc R . .
C71 C 0.44132(11) -0.0768(3) 0.74494(18) 0.0402(9) Uani 1 1 d . . .
H71A H 0.4354 -0.0145 0.7224 0.060 Uiso 1 1 calc R B .
H71B H 0.4606 -0.1165 0.7205 0.060 Uiso 1 1 calc R . .
H71C H 0.4574 -0.0665 0.7908 0.060 Uiso 1 1 calc R . .
C72 C 0.36388(13) -0.0667(3) 0.78186(16) 0.0402(9) Uani 1 1 d . . .
H72A H 0.3799 -0.0498 0.8268 0.060 Uiso 1 1 calc R B .
H72B H 0.3357 -0.1030 0.7854 0.060 Uiso 1 1 calc R . .
H72C H 0.3557 -0.0076 0.7560 0.060 Uiso 1 1 calc R . .
C8 C 0.40972(13) -0.2169(2) 0.62121(18) 0.0200(8) Uani 0.850(5) 1 d PDU B 1
H8 H 0.4346 -0.1680 0.6199 0.024 Uiso 0.850(5) 1 calc PR B 1
C81 C 0.43264(17) -0.3047(3) 0.6583(3) 0.0392(14) Uani 0.850(5) 1 d PDU B 1
H81A H 0.4103 -0.3577 0.6555 0.059 Uiso 0.850(5) 1 calc PR B 1
H81B H 0.4432 -0.2880 0.7054 0.059 Uiso 0.850(5) 1 calc PR B 1
H81C H 0.4591 -0.3247 0.6379 0.059 Uiso 0.850(5) 1 calc PR B 1
C82 C 0.38890(14) -0.2392(3) 0.54877(19) 0.0337(10) Uani 0.850(5) 1 d PD B 1
H82A H 0.4135 -0.2588 0.5242 0.051 Uiso 0.850(5) 1 calc PR B 1
H82B H 0.3735 -0.1815 0.5278 0.051 Uiso 0.850(5) 1 calc PR B 1
H82C H 0.3663 -0.2915 0.5477 0.051 Uiso 0.850(5) 1 calc PR B 1
C8' C 0.3911(6) -0.2376(11) 0.5990(8) 0.007(3) Uiso 0.150(5) 1 d PDU B 2
H8' H 0.3646 -0.2714 0.5710 0.008 Uiso 0.150(5) 1 calc PR B 2
C81' C 0.4236(10) -0.3142(17) 0.6339(12) 0.020 Uiso 0.150(5) 1 d PDU B 2
H81D H 0.4074 -0.3529 0.6632 0.030 Uiso 0.150(5) 1 calc PR B 2
H81E H 0.4505 -0.2829 0.6608 0.030 Uiso 0.150(5) 1 calc PR B 2
H81F H 0.4340 -0.3561 0.6003 0.030 Uiso 0.150(5) 1 calc PR B 2
C82' C 0.4140(6) -0.1735(13) 0.5527(9) 0.020 Uiso 0.150(5) 1 d PD B 2
H82D H 0.3918 -0.1252 0.5318 0.030 Uiso 0.150(5) 1 calc PR B 2
H82E H 0.4242 -0.2132 0.5178 0.030 Uiso 0.150(5) 1 calc PR B 2
H82F H 0.4408 -0.1410 0.5787 0.030 Uiso 0.150(5) 1 calc PR B 2
H01 H 0.5000 0.200(6) 0.7500 0.11(3) Uiso 1 2 d S . .
H02 H 0.3666(18) 0.008(4) 0.623(2) 0.103(19) Uiso 1 1 d . . .
H03 H 0.2500 -0.2500 0.5000 0.071(19) Uiso 1 2 d S . .


_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.


 Non-bonded distances

      2.4110 (0.0025)  O2 - O3
      2.4177 (0.0034)  O1 - O1_$1
      2.4228 (0.0034)  O4 - O4_$2

 Operators for generating equivalent atoms:

 $1   -x+1, y, -z+3/2
 $2   -x+1/2, -y-1/2, -z+1
;

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
Se1 Se2 2.2793(4) . ?
Se1 Br2 2.5029(4) . ?
Se1 Br1 2.7726(4) . ?
Se2 Br3 2.5276(4) . ?
Se2 Br4 2.7447(4) . ?
P1 O1 1.5289(18) . ?
P1 C2 1.807(3) . ?
P1 C1 1.807(3) . ?
P1 C01 1.816(2) . ?
P2 O2 1.5193(18) . ?
P2 C3 1.804(4) . ?
P2 C01 1.805(3) . ?
P2 C4 1.808(3) . ?
P2 C3' 1.850(13) . ?
P3 O3 1.5265(18) . ?
P3 C02 1.801(3) . ?
P3 C8 1.808(3) . ?
P3 C7 1.813(3) . ?
P3 C8' 1.908(17) . ?
P4 O4 1.5276(18) . ?
P4 C6 1.803(3) . ?
P4 C5 1.811(3) . ?
P4 C02 1.812(3) . ?
C1 C12 1.530(4) . ?
C1 C11 1.536(4) . ?
C2 C21 1.535(4) . ?
C2 C22 1.536(4) . ?
C3 C31 1.526(5) . ?
C3 C32 1.527(6) . ?
C3' C31' 1.504(12) . ?
C3' C32' 1.520(15) . ?
C4 C41 1.518(4) . ?
C4 C42 1.533(4) . ?
C5 C52 1.527(4) . ?
C5 C51 1.534(4) . ?
C6 C62 1.525(4) . ?
C6 C61 1.539(4) . ?
C7 C72 1.523(5) . ?
C7 C71 1.528(4) . ?
C8 C82 1.524(5) . ?
C8 C81 1.526(5) . ?
C8' C81' 1.521(15) . ?
C8' C82' 1.526(14) . ?

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
Se2 Se1 Br2 100.123(14) . . ?
Se2 Se1 Br1 100.456(13) . . ?
Br2 Se1 Br1 159.406(14) . . ?
Se1 Se2 Br3 98.207(14) . . ?
Se1 Se2 Br4 100.443(13) . . ?
Br3 Se2 Br4 161.319(14) . . ?
O1 P1 C2 110.81(11) . . ?
O1 P1 C1 112.03(12) . . ?
C2 P1 C1 109.05(13) . . ?
O1 P1 C01 110.03(11) . . ?
C2 P1 C01 107.92(12) . . ?
C1 P1 C01 106.84(12) . . ?
O2 P2 C3 111.78(13) . . ?
O2 P2 C01 110.66(11) . . ?
C3 P2 C01 111.91(16) . . ?
O2 P2 C4 111.06(12) . . ?
C3 P2 C4 105.82(17) . . ?
C01 P2 C4 105.33(12) . . ?
O2 P2 C3' 109.2(4) . . ?
C3 P2 C3' 17.7(4) . . ?
C01 P2 C3' 97.9(4) . . ?
C4 P2 C3' 121.5(5) . . ?
O3 P3 C02 110.44(11) . . ?
O3 P3 C8 111.58(13) . . ?
C02 P3 C8 110.88(15) . . ?
O3 P3 C7 111.16(13) . . ?
C02 P3 C7 105.38(12) . . ?
C8 P3 C7 107.19(17) . . ?
O3 P3 C8' 105.7(4) . . ?
C02 P3 C8' 95.1(5) . . ?
C8 P3 C8' 21.8(5) . . ?
C7 P3 C8' 127.4(6) . . ?
O4 P4 C6 111.96(12) . . ?
O4 P4 C5 109.42(12) . . ?
C6 P4 C5 109.56(13) . . ?
O4 P4 C02 111.34(11) . . ?
C6 P4 C02 107.82(12) . . ?
C5 P4 C02 106.57(12) . . ?
P2 C01 P1 119.81(13) . . ?
P3 C02 P4 120.93(14) . . ?
C12 C1 C11 110.7(2) . . ?
C12 C1 P1 111.31(19) . . ?
C11 C1 P1 110.2(2) . . ?
C21 C2 C22 111.7(2) . . ?
C21 C2 P1 113.00(19) . . ?
C22 C2 P1 110.85(18) . . ?
C31 C3 C32 112.0(5) . . ?
C31 C3 P2 112.2(3) . . ?
C32 C3 P2 112.4(5) . . ?
C31' C3' C32' 114.1(19) . . ?
C31' C3' P2 111.4(9) . . ?
C32' C3' P2 110.6(18) . . ?
C41 C4 C42 110.1(2) . . ?
C41 C4 P2 110.4(2) . . ?
C42 C4 P2 112.4(2) . . ?
C52 C5 C51 111.9(2) . . ?
C52 C5 P4 113.6(2) . . ?
C51 C5 P4 109.47(19) . . ?
C62 C6 C61 110.4(2) . . ?
C62 C6 P4 110.37(19) . . ?
C61 C6 P4 111.27(19) . . ?
C72 C7 C71 110.8(3) . . ?
C72 C7 P3 110.6(2) . . ?
C71 C7 P3 111.6(2) . . ?
C82 C8 C81 112.7(3) . . ?
C82 C8 P3 110.0(3) . . ?
C81 C8 P3 113.1(3) . . ?
C81' C8' C82' 112.7(16) . . ?
C81' C8' P3 110.3(14) . . ?
C82' C8' P3 110.4(12) . . ?

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
Br2 Se1 Se2 Br3 91.425(15) . . . . ?
Br1 Se1 Se2 Br3 -87.787(14) . . . . ?
Br2 Se1 Se2 Br4 -89.659(14) . . . . ?
Br1 Se1 Se2 Br4 91.129(13) . . . . ?
O2 P2 C01 P1 -36.76(18) . . . . ?
C3 P2 C01 P1 88.6(2) . . . . ?
C4 P2 C01 P1 -156.87(16) . . . . ?
C3' P2 C01 P1 77.3(4) . . . . ?
O1 P1 C01 P2 -22.52(19) . . . . ?
C2 P1 C01 P2 -143.54(15) . . . . ?
C1 P1 C01 P2 99.32(17) . . . . ?
O3 P3 C02 P4 26.5(2) . . . . ?
C8 P3 C02 P4 -97.7(2) . . . . ?
C7 P3 C02 P4 146.61(17) . . . . ?
C8' P3 C02 P4 -82.3(5) . . . . ?
O4 P4 C02 P3 26.3(2) . . . . ?
C6 P4 C02 P3 -96.89(18) . . . . ?
C5 P4 C02 P3 145.56(16) . . . . ?
O1 P1 C1 C12 57.6(2) . . . . ?
C2 P1 C1 C12 -179.34(19) . . . . ?
C01 P1 C1 C12 -62.9(2) . . . . ?
O1 P1 C1 C11 -65.6(2) . . . . ?
C2 P1 C1 C11 57.4(2) . . . . ?
C01 P1 C1 C11 173.8(2) . . . . ?
O1 P1 C2 C21 174.93(19) . . . . ?
C1 P1 C2 C21 51.2(2) . . . . ?
C01 P1 C2 C21 -64.5(2) . . . . ?
O1 P1 C2 C22 -58.7(2) . . . . ?
C1 P1 C2 C22 177.50(18) . . . . ?
C01 P1 C2 C22 61.8(2) . . . . ?
O2 P2 C3 C31 48.7(3) . . . . ?
C01 P2 C3 C31 -76.1(3) . . . . ?
C4 P2 C3 C31 169.7(3) . . . . ?
C3' P2 C3 C31 -36.4(12) . . . . ?
O2 P2 C3 C32 176.0(5) . . . . ?
C01 P2 C3 C32 51.3(6) . . . . ?
C4 P2 C3 C32 -62.9(6) . . . . ?
C3' P2 C3 C32 91.0(15) . . . . ?
O2 P2 C3' C31' -37.4(11) . . . . ?
C3 P2 C3' C31' 64.1(13) . . . . ?
C01 P2 C3' C31' -152.6(9) . . . . ?
C4 P2 C3' C31' 93.9(9) . . . . ?
O2 P2 C3' C32' -165(2) . . . . ?
C3 P2 C3' C32' -64(2) . . . . ?
C01 P2 C3' C32' 79(2) . . . . ?
C4 P2 C3' C32' -34(2) . . . . ?
O2 P2 C4 C41 -46.2(2) . . . . ?
C3 P2 C4 C41 -167.7(2) . . . . ?
C01 P2 C4 C41 73.7(2) . . . . ?
C3' P2 C4 C41 -176.7(5) . . . . ?
O2 P2 C4 C42 77.1(2) . . . . ?
C3 P2 C4 C42 -44.3(3) . . . . ?
C01 P2 C4 C42 -163.0(2) . . . . ?
C3' P2 C4 C42 -53.4(5) . . . . ?
O4 P4 C5 C52 -178.5(2) . . . . ?
C6 P4 C5 C52 -55.4(2) . . . . ?
C02 P4 C5 C52 61.0(2) . . . . ?
O4 P4 C5 C51 55.6(2) . . . . ?
C6 P4 C5 C51 178.73(19) . . . . ?
C02 P4 C5 C51 -64.9(2) . . . . ?
O4 P4 C6 C62 66.3(2) . . . . ?
C5 P4 C6 C62 -55.3(2) . . . . ?
C02 P4 C6 C62 -170.91(19) . . . . ?
O4 P4 C6 C61 -56.7(2) . . . . ?
C5 P4 C6 C61 -178.26(19) . . . . ?
C02 P4 C6 C61 66.1(2) . . . . ?
O3 P3 C7 C72 48.9(2) . . . . ?
C02 P3 C7 C72 -70.8(2) . . . . ?
C8 P3 C7 C72 171.0(2) . . . . ?
C8' P3 C7 C72 -179.8(6) . . . . ?
O3 P3 C7 C71 -75.0(3) . . . . ?
C02 P3 C7 C71 165.3(2) . . . . ?
C8 P3 C7 C71 47.1(3) . . . . ?
C8' P3 C7 C71 56.3(6) . . . . ?
O3 P3 C8 C82 -53.6(3) . . . . ?
C02 P3 C8 C82 69.9(3) . . . . ?
C7 P3 C8 C82 -175.5(2) . . . . ?
C8' P3 C8 C82 24.4(11) . . . . ?
O3 P3 C8 C81 179.4(3) . . . . ?
C02 P3 C8 C81 -57.1(3) . . . . ?
C7 P3 C8 C81 57.4(3) . . . . ?
C8' P3 C8 C81 -102.6(12) . . . . ?
O3 P3 C8' C81' 166.1(14) . . . . ?
C02 P3 C8' C81' -81.0(15) . . . . ?
C8 P3 C8' C81' 57.1(16) . . . . ?
C7 P3 C8' C81' 32.8(17) . . . . ?
O3 P3 C8' C82' 41.0(13) . . . . ?
C02 P3 C8' C82' 153.9(12) . . . . ?
C8 P3 C8' C82' -68.1(15) . . . . ?
C7 P3 C8' C82' -92.4(12) . . . . ?

_diffrn_measured_fraction_theta_max 0.991
_diffrn_reflns_theta_full        30.03
_diffrn_measured_fraction_theta_full 0.991
_refine_diff_density_max         1.554
_refine_diff_density_min         -0.745
_refine_diff_density_rms         0.117


# end of cif file
####################################################################### 
# 
# 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_tywin
_database_code_depnum_ccdc_archive 'CCDC 1574230'
_audit_update_record             
;
2017-09-13 deposited with the CCDC.
2018-02-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H32 Br4 P2 Se2'
_chemical_formula_weight         739.90

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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 2/c'

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

_cell_length_a                   16.2568(5)
_cell_length_b                   9.4204(3)
_cell_length_c                   15.9393(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 107.253(4)
_cell_angle_gamma                90.00
_cell_volume                     2331.19(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    14377
_cell_measurement_theta_min      2.5040
_cell_measurement_theta_max      29.5910

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.10
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    2.108
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1416
_exptl_absorpt_coefficient_mu    10.161
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.66876
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur, Eos'
_diffrn_measurement_method       ω-scan
_diffrn_detector_area_resol_mean 16.1419
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            87552
_diffrn_reflns_av_R_equivalents  0.0693
_diffrn_reflns_av_sigmaI/netI    0.0258
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.53
_diffrn_reflns_theta_max         30.03
_reflns_number_total             3402
_reflns_number_gt                3114
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Siemens XP'
_computing_publication_material  SHELXL-97

_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)+(0.0176P)²+4.7085P] 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_number_reflns         3402
_refine_ls_number_parameters     104
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0385
_refine_ls_R_factor_gt           0.0323
_refine_ls_wR_factor_ref         0.0531
_refine_ls_wR_factor_gt          0.0517
_refine_ls_goodness_of_fit_ref   1.205
_refine_ls_restrained_S_all      1.205
_refine_ls_shift/su_max          0.002
_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
Se1 Se 0.372188(15) 0.69862(3) 0.721251(16) 0.01050(6) Uani 1 1 d . . .
Br1 Br 0.447854(16) 0.83931(3) 0.627671(18) 0.01826(7) Uani 1 1 d . . .
Br2 Br 0.313258(17) 0.55640(3) 0.830495(16) 0.01424(6) Uani 1 1 d . . .
P1 P 0.29365(4) 0.57556(6) 0.60299(4) 0.00812(12) Uani 1 1 d . . .
C01 C 0.26976(16) 0.6761(2) 0.50033(15) 0.0093(5) Uani 1 1 d . . .
H1A H 0.3240 0.6867 0.4846 0.011 Uiso 1 1 calc R . .
H1B H 0.2299 0.6189 0.4535 0.011 Uiso 1 1 calc R . .
C1 C 0.35673(16) 0.4223(3) 0.58772(17) 0.0117(5) Uani 1 1 d . . .
H2 H 0.3231 0.3733 0.5326 0.014 Uiso 1 1 calc R . .
C11 C 0.36962(17) 0.3161(3) 0.66298(18) 0.0163(5) Uani 1 1 d . . .
H3A H 0.4028 0.2346 0.6525 0.024 Uiso 1 1 calc R . .
H3B H 0.3134 0.2837 0.6663 0.024 Uiso 1 1 calc R . .
H3C H 0.4010 0.3619 0.7184 0.024 Uiso 1 1 calc R . .
C12 C 0.44372(18) 0.4640(3) 0.5766(2) 0.0206(6) Uani 1 1 d . . .
H4A H 0.4786 0.5115 0.6300 0.031 Uiso 1 1 calc R . .
H4B H 0.4346 0.5287 0.5265 0.031 Uiso 1 1 calc R . .
H4C H 0.4737 0.3787 0.5661 0.031 Uiso 1 1 calc R . .
C2 C 0.19376(15) 0.5091(3) 0.61948(17) 0.0110(5) Uani 1 1 d . . .
H5 H 0.2106 0.4550 0.6760 0.013 Uiso 1 1 calc R . .
C21 C 0.13265(17) 0.6274(3) 0.62981(18) 0.0166(5) Uani 1 1 d . . .
H6A H 0.1014 0.6651 0.5718 0.025 Uiso 1 1 calc R . .
H6B H 0.1661 0.7037 0.6661 0.025 Uiso 1 1 calc R . .
H6C H 0.0915 0.5890 0.6581 0.025 Uiso 1 1 calc R . .
C22 C 0.14955(17) 0.4026(3) 0.54700(17) 0.0147(5) Uani 1 1 d . . .
H7A H 0.0956 0.3700 0.5561 0.022 Uiso 1 1 calc R . .
H7B H 0.1877 0.3213 0.5492 0.022 Uiso 1 1 calc R . .
H7C H 0.1372 0.4488 0.4895 0.022 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
Se1 P1 2.2583(7) . ?
Se1 Br1 2.5657(4) . ?
Se1 Br2 2.5951(4) . ?
P1 C1 1.829(2) . ?
P1 C01 1.830(2) . ?
P1 C2 1.831(2) . ?
C01 C01 1.531(5) 7_566 ?
C1 C11 1.528(3) . ?
C1 C12 1.528(4) . ?
C2 C21 1.534(4) . ?
C2 C22 1.538(3) . ?

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
P1 Se1 Br1 91.705(18) . . ?
P1 Se1 Br2 93.740(18) . . ?
Br1 Se1 Br2 173.137(13) . . ?
C1 P1 C01 105.57(11) . . ?
C1 P1 C2 107.78(12) . . ?
C01 P1 C2 110.09(12) . . ?
C1 P1 Se1 108.41(9) . . ?
C01 P1 Se1 113.46(8) . . ?
C2 P1 Se1 111.21(8) . . ?
C01 C01 P1 117.0(2) 7_566 . ?
C11 C1 C12 110.1(2) . . ?
C11 C1 P1 111.35(17) . . ?
C12 C1 P1 112.77(18) . . ?
C21 C2 C22 112.4(2) . . ?
C21 C2 P1 113.39(17) . . ?
C22 C2 P1 110.61(17) . . ?

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
Br1 Se1 P1 C1 86.17(9) . . . . ?
Br2 Se1 P1 C1 -89.65(9) . . . . ?
Br1 Se1 P1 C01 -30.76(9) . . . . ?
Br2 Se1 P1 C01 153.42(9) . . . . ?
Br1 Se1 P1 C2 -155.51(9) . . . . ?
Br2 Se1 P1 C2 28.67(9) . . . . ?
C1 P1 C01 C01 -170.1(2) . . . 7_566 ?
C2 P1 C01 C01 73.9(3) . . . 7_566 ?
Se1 P1 C01 C01 -51.5(3) . . . 7_566 ?
C01 P1 C1 C11 -171.18(18) . . . . ?
C2 P1 C1 C11 -53.5(2) . . . . ?
Se1 P1 C1 C11 66.93(19) . . . . ?
C01 P1 C1 C12 64.5(2) . . . . ?
C2 P1 C1 C12 -177.89(19) . . . . ?
Se1 P1 C1 C12 -57.4(2) . . . . ?
C1 P1 C2 C21 -177.84(18) . . . . ?
C01 P1 C2 C21 -63.2(2) . . . . ?
Se1 P1 C2 C21 63.46(19) . . . . ?
C1 P1 C2 C22 -50.5(2) . . . . ?
C01 P1 C2 C22 64.2(2) . . . . ?
Se1 P1 C2 C22 -169.21(14) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        30.03
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.601
_refine_diff_density_min         -0.576
_refine_diff_density_rms         0.120

####################################################################### 
# 
# 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_theon
_database_code_depnum_ccdc_archive 'CCDC 1574231'
_audit_update_record             
;
2017-09-13 deposited with the CCDC.
2018-02-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H32 I4 P2 Se2'
_chemical_formula_weight         927.86

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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.7755(7)
_cell_length_b                   9.3550(8)
_cell_length_c                   9.4012(9)
_cell_angle_alpha                105.549(8)
_cell_angle_beta                 98.760(8)
_cell_angle_gamma                98.357(8)
_cell_volume                     638.56(10)
_cell_formula_units_Z            1
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7113
_cell_measurement_theta_min      2.6930
_cell_measurement_theta_max      30.6740

_exptl_crystal_description       block
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    2.413
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             426
_exptl_absorpt_coefficient_mu    7.852
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.47268
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur, Eos'
_diffrn_measurement_method       ω-scan
_diffrn_detector_area_resol_mean 16.1419
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            24473
_diffrn_reflns_av_R_equivalents  0.0410
_diffrn_reflns_av_sigmaI/netI    0.0302
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.30
_diffrn_reflns_theta_max         31.03
_reflns_number_total             3805
_reflns_number_gt                3313
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Siemens XP'
_computing_publication_material  SHELXL-97

_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)+(0.0117P)²+0.1356P] 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     SHELXL
_refine_ls_extinction_coef       0.00257(15)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3805
_refine_ls_number_parameters     105
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0287
_refine_ls_R_factor_gt           0.0220
_refine_ls_wR_factor_ref         0.0401
_refine_ls_wR_factor_gt          0.0382
_refine_ls_goodness_of_fit_ref   1.037
_refine_ls_restrained_S_all      1.037
_refine_ls_shift/su_max          0.003
_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
I1 I 0.120010(18) 0.737122(17) 0.529446(16) 0.01147(5) Uani 1 1 d . . .
I2 I -0.10563(2) 0.796957(19) 0.287462(18) 0.01860(5) Uani 1 1 d . . .
Se1 Se 0.31957(3) 0.68359(3) 0.77668(3) 0.01312(6) Uani 1 1 d . . .
P1 P 0.58069(7) 0.68233(7) 0.72333(7) 0.00956(12) Uani 1 1 d . . .
C01 C 0.5729(3) 0.5717(3) 0.5295(2) 0.0116(5) Uani 1 1 d . . .
H01A H 0.5544 0.6366 0.4631 0.014 Uiso 1 1 calc R . .
H01B H 0.6892 0.5420 0.5228 0.014 Uiso 1 1 calc R . .
C1 C 0.7031(3) 0.6030(3) 0.8554(3) 0.0124(5) Uani 1 1 d . . .
H1 H 0.6947 0.6629 0.9587 0.015 Uiso 1 1 calc R . .
C12 C 0.9008(3) 0.6219(3) 0.8502(3) 0.0147(5) Uani 1 1 d . . .
H12A H 0.9632 0.5882 0.9302 0.022 Uiso 1 1 calc R . .
H12B H 0.9499 0.7286 0.8652 0.022 Uiso 1 1 calc R . .
H12C H 0.9157 0.5610 0.7520 0.022 Uiso 1 1 calc R . .
C11 C 0.6235(3) 0.4382(3) 0.8371(3) 0.0174(5) Uani 1 1 d . . .
H11A H 0.6475 0.3729 0.7447 0.026 Uiso 1 1 calc R . .
H11B H 0.4950 0.4267 0.8308 0.026 Uiso 1 1 calc R . .
H11C H 0.6770 0.4094 0.9240 0.026 Uiso 1 1 calc R . .
C2 C 0.7047(3) 0.8716(3) 0.7465(3) 0.0132(5) Uani 1 1 d . . .
H2 H 0.8203 0.8605 0.7149 0.016 Uiso 1 1 calc R . .
C22 C 0.6066(3) 0.9522(3) 0.6472(3) 0.0198(6) Uani 1 1 d . . .
H22A H 0.4935 0.9664 0.6774 0.030 Uiso 1 1 calc R . .
H22B H 0.5840 0.8908 0.5415 0.030 Uiso 1 1 calc R . .
H22C H 0.6795 1.0511 0.6593 0.030 Uiso 1 1 calc R . .
C21 C 0.7451(3) 0.9682(3) 0.9114(3) 0.0195(5) Uani 1 1 d . . .
H21A H 0.8111 1.0689 0.9207 0.029 Uiso 1 1 calc R . .
H21B H 0.8164 0.9200 0.9729 0.029 Uiso 1 1 calc R . .
H21C H 0.6336 0.9777 0.9463 0.029 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
I1 Se1 2.7950(4) . ?
I1 I2 2.8843(3) . ?
Se1 P1 2.1652(6) . ?
P1 C01 1.826(2) . ?
P1 C1 1.827(2) . ?
P1 C2 1.829(2) . ?
C01 C01 1.535(4) 2_666 ?
C1 C11 1.529(3) . ?
C1 C12 1.531(3) . ?
C2 C21 1.528(3) . ?
C2 C22 1.533(3) . ?

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
Se1 I1 I2 175.764(8) . . ?
P1 Se1 I1 104.162(19) . . ?
C01 P1 C1 110.31(11) . . ?
C01 P1 C2 106.23(11) . . ?
C1 P1 C2 107.89(11) . . ?
C01 P1 Se1 112.65(7) . . ?
C1 P1 Se1 106.62(7) . . ?
C2 P1 Se1 113.06(8) . . ?
C01 C01 P1 114.4(2) 2_666 . ?
C11 C1 C12 110.8(2) . . ?
C11 C1 P1 113.39(15) . . ?
C12 C1 P1 112.29(16) . . ?
C21 C2 C22 110.0(2) . . ?
C21 C2 P1 111.10(17) . . ?
C22 C2 P1 111.95(16) . . ?

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
I1 Se1 P1 C01 -45.32(9) . . . . ?
I1 Se1 P1 C1 -166.47(8) . . . . ?
I1 Se1 P1 C2 75.13(8) . . . . ?
C1 P1 C01 C01 82.3(2) . . . 2_666 ?
C2 P1 C01 C01 -161.1(2) . . . 2_666 ?
Se1 P1 C01 C01 -36.8(3) . . . 2_666 ?
C01 P1 C1 C11 -58.61(19) . . . . ?
C2 P1 C1 C11 -174.25(16) . . . . ?
Se1 P1 C1 C11 64.02(17) . . . . ?
C01 P1 C1 C12 67.91(19) . . . . ?
C2 P1 C1 C12 -47.7(2) . . . . ?
Se1 P1 C1 C12 -169.47(15) . . . . ?
C01 P1 C2 C21 -171.21(17) . . . . ?
C1 P1 C2 C21 -52.92(19) . . . . ?
Se1 P1 C2 C21 64.74(18) . . . . ?
C01 P1 C2 C22 65.34(19) . . . . ?
C1 P1 C2 C22 -176.37(16) . . . . ?
Se1 P1 C2 C22 -58.71(18) . . . . ?

_diffrn_measured_fraction_theta_max 0.931
_diffrn_reflns_theta_full        30.00
_diffrn_measured_fraction_theta_full 0.988
_refine_diff_density_max         0.615
_refine_diff_density_min         -0.629
_refine_diff_density_rms         0.137


#=============================================================================
# end of cif data for "theon"
#=============================================================================

#=============================================================================
# end of combined cif file
#=============================================================================
####################################################################### 
# 
# 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_megan_5
_database_code_depnum_ccdc_archive 'CCDC 1578393'
_audit_update_record             
;
2017-10-06 deposited with the CCDC.
2018-02-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C50 H44 I8 P4 Se4'
_chemical_formula_weight         2099.77

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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.4767(3)
_cell_length_b                   15.5810(8)
_cell_length_c                   18.6525(9)
_cell_angle_alpha                88.335(4)
_cell_angle_beta                 77.260(3)
_cell_angle_gamma                89.954(3)
_cell_volume                     2968.5(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    26453
_cell_measurement_theta_min      2.4280
_cell_measurement_theta_max      29.9790

_exptl_crystal_description       lath
_exptl_crystal_colour            'dark red'
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.349
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1928
_exptl_absorpt_coefficient_mu    6.773
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.64225
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur, Eos'
_diffrn_measurement_method       'ω scan'
_diffrn_detector_area_resol_mean 16.1419
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            18267
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0683
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.24
_diffrn_reflns_theta_max         30.03
_reflns_number_total             18267
_reflns_number_gt                13994
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker XP'
_computing_publication_material  SHELXL-97

_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.

 The crystal was a non-merohedral twin (by 180 degree rotation about a*).
 The structure was refined using the "HKLF 5" method. The relative volume of
 the smaller component refined to 0.3642(6). All equivalent reflections
 are merged when generating the intensity file, so that R(int) is
 meaningless. Because the intensity file is a mixture of overlapped and
 non-overlapped reflections, the quoted numer of reflections should be
 interpreted with caution.
;

_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)+(0.0672P)²] 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_number_reflns         18267
_refine_ls_number_parameters     599
_refine_ls_number_restraints     300
_refine_ls_R_factor_all          0.0635
_refine_ls_R_factor_gt           0.0449
_refine_ls_wR_factor_ref         0.1140
_refine_ls_wR_factor_gt          0.1100
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_restrained_S_all      1.011
_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
I1 I 0.5000 0.5000 0.5000 0.01590(15) Uani 1 2 d S . .
I2 I 0.17104(5) 0.29777(3) 0.81846(3) 0.01535(12) Uani 1 1 d . . .
I3 I 0.02148(6) 0.18602(4) 0.93464(3) 0.02246(13) Uani 1 1 d . . .
I4 I 0.0000 0.0000 0.5000 0.01072(14) Uani 1 2 d S . .
I5 I 0.46804(5) -0.20036(3) 0.81460(3) 0.01227(11) Uani 1 1 d . . .
I6 I 0.52162(6) -0.31001(4) 0.93372(3) 0.01995(13) Uani 1 1 d . . .
I7 I 0.60127(6) 0.12133(4) 0.61606(4) 0.02590(14) Uani 1 1 d . . .
I8 I 0.70453(5) 0.24306(3) 0.49541(3) 0.01694(12) Uani 1 1 d . . .
I9 I 0.81245(5) 0.36470(4) 0.37367(3) 0.02147(13) Uani 1 1 d . . .
Se1 Se 0.67072(9) 0.45409(6) 0.58543(5) 0.02124(19) Uani 1 1 d . . .
Se2 Se 0.30252(8) 0.40800(5) 0.70550(5) 0.01543(17) Uani 1 1 d . . .
Se3 Se 0.19198(8) -0.02790(5) 0.58120(4) 0.01157(16) Uani 1 1 d . . .
Se4 Se 0.42502(8) -0.08761(5) 0.70246(4) 0.01268(16) Uani 1 1 d . . .
P1 P 0.6505(2) 0.55756(13) 0.66289(11) 0.0101(4) Uani 1 1 d . . .
P2 P 0.40856(19) 0.47333(12) 0.77523(11) 0.0090(4) Uani 1 1 d . . .
P3 P 0.11481(19) 0.06568(12) 0.66287(11) 0.0083(4) Uani 1 1 d . . .
P4 P 0.2653(2) -0.02333(12) 0.77492(11) 0.0086(4) Uani 1 1 d . . .
C01 C 0.4893(8) 0.5679(5) 0.7234(4) 0.0146(17) Uani 1 1 d U . .
H01A H 0.4298 0.5911 0.6931 0.018 Uiso 1 1 calc R . .
H01B H 0.4964 0.6120 0.7595 0.018 Uiso 1 1 calc R . .
C02 C 0.2214(8) 0.0737(5) 0.7281(4) 0.0109(15) Uani 1 1 d U . .
H02A H 0.1792 0.1135 0.7666 0.013 Uiso 1 1 calc R . .
H02B H 0.3040 0.1015 0.7015 0.013 Uiso 1 1 calc R . .
C11 C 0.7681(7) 0.5365(5) 0.7190(4) 0.0088(15) Uani 1 1 d U . .
C12 C 0.7761(8) 0.5921(5) 0.7762(4) 0.0137(16) Uani 1 1 d U . .
H12 H 0.7188 0.6398 0.7859 0.016 Uiso 1 1 calc R . .
C13 C 0.8681(8) 0.5769(5) 0.8183(4) 0.0151(16) Uani 1 1 d U . .
H13 H 0.8743 0.6140 0.8569 0.018 Uiso 1 1 calc R . .
C14 C 0.9507(9) 0.5074(6) 0.8038(5) 0.0210(19) Uani 1 1 d U . .
H14 H 1.0129 0.4969 0.8331 0.025 Uiso 1 1 calc R . .
C15 C 0.9449(9) 0.4530(6) 0.7478(5) 0.022(2) Uani 1 1 d U . .
H15 H 1.0026 0.4056 0.7384 0.027 Uiso 1 1 calc R . .
C16 C 0.8519(8) 0.4687(5) 0.7045(5) 0.0178(18) Uani 1 1 d U . .
H16 H 0.8477 0.4321 0.6652 0.021 Uiso 1 1 calc R . .
C21 C 0.6848(8) 0.6636(5) 0.6251(4) 0.0112(16) Uani 1 1 d U . .
C22 C 0.8068(8) 0.6989(5) 0.6163(4) 0.0115(16) Uani 1 1 d U . .
H22 H 0.8752 0.6656 0.6287 0.014 Uiso 1 1 calc R . .
C23 C 0.8324(8) 0.7820(5) 0.5895(4) 0.0154(17) Uani 1 1 d U . .
H23 H 0.9179 0.8054 0.5838 0.018 Uiso 1 1 calc R . .
C24 C 0.7348(8) 0.8314(6) 0.5708(5) 0.0191(18) Uani 1 1 d U . .
H24 H 0.7516 0.8895 0.5546 0.023 Uiso 1 1 calc R . .
C25 C 0.6113(8) 0.7955(5) 0.5760(4) 0.0155(17) Uani 1 1 d U . .
H25 H 0.5447 0.8282 0.5610 0.019 Uiso 1 1 calc R . .
C26 C 0.5858(8) 0.7129(5) 0.6026(5) 0.0169(18) Uani 1 1 d U . .
H26 H 0.5015 0.6886 0.6060 0.020 Uiso 1 1 calc R . .
C31 C 0.5281(7) 0.4042(5) 0.8029(4) 0.0103(15) Uani 1 1 d U . .
C32 C 0.5849(8) 0.4267(5) 0.8609(4) 0.0109(15) Uani 1 1 d U . .
H32 H 0.5588 0.4773 0.8874 0.013 Uiso 1 1 calc R . .
C33 C 0.6812(8) 0.3732(5) 0.8793(5) 0.0191(19) Uani 1 1 d U . .
H33 H 0.7197 0.3873 0.9190 0.023 Uiso 1 1 calc R . .
C34 C 0.7201(8) 0.3014(5) 0.8409(5) 0.0164(18) Uani 1 1 d U . .
H34 H 0.7849 0.2657 0.8545 0.020 Uiso 1 1 calc R . .
C35 C 0.6653(8) 0.2790(5) 0.7809(5) 0.0175(18) Uani 1 1 d U . .
H35 H 0.6947 0.2301 0.7528 0.021 Uiso 1 1 calc R . .
C36 C 0.5663(8) 0.3316(5) 0.7645(5) 0.0177(18) Uani 1 1 d U . .
H36 H 0.5250 0.3166 0.7260 0.021 Uiso 1 1 calc R . .
C41 C 0.3032(7) 0.5170(5) 0.8548(4) 0.0084(15) Uani 1 1 d U . .
C42 C 0.2395(7) 0.5967(5) 0.8475(4) 0.0109(16) Uani 1 1 d U . .
H42 H 0.2553 0.6267 0.8013 0.013 Uiso 1 1 calc R . .
C43 C 0.1545(8) 0.6302(5) 0.9078(5) 0.0171(18) Uani 1 1 d U . .
H43 H 0.1144 0.6843 0.9035 0.021 Uiso 1 1 calc R . .
C44 C 0.1285(9) 0.5848(6) 0.9737(5) 0.0209(19) Uani 1 1 d U . .
H44 H 0.0682 0.6071 1.0145 0.025 Uiso 1 1 calc R . .
C45 C 0.1891(9) 0.5067(6) 0.9814(5) 0.0210(19) Uani 1 1 d U . .
H45 H 0.1715 0.4767 1.0277 0.025 Uiso 1 1 calc R . .
C46 C 0.2756(8) 0.4723(5) 0.9216(4) 0.0125(16) Uani 1 1 d U . .
H46 H 0.3154 0.4184 0.9267 0.015 Uiso 1 1 calc R . .
C51 C 0.1114(8) 0.1739(5) 0.6258(4) 0.0117(15) Uani 1 1 d U . .
C52 C 0.2269(8) 0.2207(5) 0.6051(4) 0.0113(15) Uani 1 1 d U . .
H52 H 0.3072 0.1960 0.6107 0.014 Uiso 1 1 calc R . .
C53 C 0.2247(8) 0.3044(5) 0.5759(5) 0.0165(17) Uani 1 1 d U . .
H53 H 0.3037 0.3366 0.5616 0.020 Uiso 1 1 calc R . .
C54 C 0.1072(8) 0.3405(5) 0.5678(4) 0.0167(17) Uani 1 1 d U . .
H54 H 0.1046 0.3977 0.5491 0.020 Uiso 1 1 calc R . .
C55 C -0.0062(8) 0.2915(5) 0.5874(4) 0.0150(17) Uani 1 1 d U . .
H55 H -0.0866 0.3152 0.5810 0.018 Uiso 1 1 calc R . .
C56 C -0.0045(8) 0.2095(5) 0.6160(4) 0.0157(17) Uani 1 1 d U . .
H56 H -0.0834 0.1771 0.6291 0.019 Uiso 1 1 calc R . .
C61 C -0.0458(7) 0.0407(5) 0.7153(4) 0.0109(16) Uani 1 1 d U . .
C62 C -0.1101(7) -0.0338(5) 0.7017(4) 0.0098(15) Uani 1 1 d U . .
H62 H -0.0683 -0.0717 0.6649 0.012 Uiso 1 1 calc R . .
C63 C -0.2351(8) -0.0518(5) 0.7424(4) 0.0141(17) Uani 1 1 d U . .
H63 H -0.2800 -0.1012 0.7317 0.017 Uiso 1 1 calc R . .
C64 C -0.2964(8) 0.0010(5) 0.7987(4) 0.0132(16) Uani 1 1 d U . .
H64 H -0.3812 -0.0127 0.8271 0.016 Uiso 1 1 calc R . .
C65 C -0.2313(8) 0.0734(5) 0.8120(4) 0.0164(17) Uani 1 1 d U . .
H65 H -0.2728 0.1097 0.8502 0.020 Uiso 1 1 calc R . .
C66 C -0.1079(8) 0.0952(5) 0.7721(4) 0.0112(15) Uani 1 1 d U . .
H66 H -0.0654 0.1457 0.7823 0.013 Uiso 1 1 calc R . .
C71 C 0.1252(7) -0.0920(5) 0.8043(4) 0.0095(15) Uani 1 1 d U . .
C72 C 0.1143(8) -0.1671(5) 0.7668(4) 0.0134(16) Uani 1 1 d U . .
H72 H 0.1831 -0.1833 0.7273 0.016 Uiso 1 1 calc R . .
C73 C 0.0050(9) -0.2172(6) 0.7869(5) 0.022(2) Uani 1 1 d U . .
H73 H -0.0010 -0.2684 0.7614 0.026 Uiso 1 1 calc R . .
C74 C -0.0976(8) -0.1950(5) 0.8437(5) 0.0161(18) Uani 1 1 d U . .
H74 H -0.1743 -0.2296 0.8563 0.019 Uiso 1 1 calc R . .
C75 C -0.0858(8) -0.1192(5) 0.8829(5) 0.0164(18) Uani 1 1 d U . .
H75 H -0.1535 -0.1043 0.9235 0.020 Uiso 1 1 calc R . .
C76 C 0.0236(8) -0.0678(5) 0.8621(5) 0.0153(17) Uani 1 1 d U . .
H76 H 0.0300 -0.0161 0.8868 0.018 Uiso 1 1 calc R . .
C81 C 0.3136(7) 0.0184(5) 0.8539(4) 0.0115(16) Uani 1 1 d U . .
C82 C 0.2858(8) -0.0279(5) 0.9212(5) 0.0170(18) Uani 1 1 d U . .
H82 H 0.2394 -0.0809 0.9260 0.020 Uiso 1 1 calc R . .
C83 C 0.3268(9) 0.0047(6) 0.9803(5) 0.0212(19) Uani 1 1 d U . .
H83 H 0.3091 -0.0269 1.0258 0.025 Uiso 1 1 calc R . .
C84 C 0.3928(9) 0.0819(6) 0.9752(5) 0.0202(19) Uani 1 1 d U . .
H84 H 0.4195 0.1034 1.0168 0.024 Uiso 1 1 calc R . .
C85 C 0.4197(8) 0.1277(5) 0.9091(5) 0.0174(18) Uani 1 1 d U . .
H85 H 0.4646 0.1812 0.9048 0.021 Uiso 1 1 calc R . .
C86 C 0.3801(8) 0.0945(5) 0.8482(4) 0.0120(16) Uani 1 1 d U . .
H86 H 0.3998 0.1255 0.8024 0.014 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
I1 Se1 2.7274(9) 2_666 ?
I1 Se1 2.7274(9) . ?
I2 Se2 2.7928(10) . ?
I2 I3 2.9105(8) . ?
I4 Se3 2.7986(8) 2_556 ?
I4 Se3 2.7987(8) . ?
I5 Se4 2.8046(9) . ?
I5 I6 2.9152(8) . ?
I7 I8 2.9178(9) . ?
I8 I9 2.9408(9) . ?
Se1 P1 2.175(2) . ?
Se2 P2 2.163(2) . ?
Se3 P3 2.164(2) . ?
Se4 P4 2.170(2) . ?
P1 C21 1.783(8) . ?
P1 C11 1.808(8) . ?
P1 C01 1.822(8) . ?
P2 C41 1.794(8) . ?
P2 C31 1.801(8) . ?
P2 C01 1.839(8) . ?
P3 C61 1.787(8) . ?
P3 C51 1.807(8) . ?
P3 C02 1.831(8) . ?
P4 C71 1.793(8) . ?
P4 C81 1.799(8) . ?
P4 C02 1.833(8) . ?
C11 C16 1.368(11) . ?
C11 C12 1.411(10) . ?
C12 C13 1.388(11) . ?
C13 C14 1.380(12) . ?
C14 C15 1.375(12) . ?
C15 C16 1.413(12) . ?
C21 C22 1.366(11) . ?
C21 C26 1.419(11) . ?
C22 C23 1.379(11) . ?
C23 C24 1.378(11) . ?
C24 C25 1.393(11) . ?
C25 C26 1.370(11) . ?
C31 C36 1.368(11) . ?
C31 C32 1.399(10) . ?
C32 C33 1.401(11) . ?
C33 C34 1.359(11) . ?
C34 C35 1.418(11) . ?
C35 C36 1.402(12) . ?
C41 C46 1.382(11) . ?
C41 C42 1.426(10) . ?
C42 C43 1.387(11) . ?
C43 C44 1.374(12) . ?
C44 C45 1.390(12) . ?
C45 C46 1.394(11) . ?
C51 C56 1.380(11) . ?
C51 C52 1.387(11) . ?
C52 C53 1.401(11) . ?
C53 C54 1.390(12) . ?
C54 C55 1.386(11) . ?
C55 C56 1.372(11) . ?
C61 C62 1.400(10) . ?
C61 C66 1.418(10) . ?
C62 C63 1.385(11) . ?
C63 C64 1.394(11) . ?
C64 C65 1.376(11) . ?
C65 C66 1.379(11) . ?
C71 C72 1.398(10) . ?
C71 C76 1.398(11) . ?
C72 C73 1.362(11) . ?
C73 C74 1.383(12) . ?
C74 C75 1.426(11) . ?
C75 C76 1.376(11) . ?
C81 C86 1.365(10) . ?
C81 C82 1.403(11) . ?
C82 C83 1.378(12) . ?
C83 C84 1.379(12) . ?
C84 C85 1.381(12) . ?
C85 C86 1.404(11) . ?

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
Se1 I1 Se1 180.0 2_666 . ?
Se2 I2 I3 177.08(3) . . ?
Se3 I4 Se3 180.0 2_556 . ?
Se4 I5 I6 176.77(3) . . ?
I7 I8 I9 179.16(3) . . ?
P1 Se1 I1 102.78(6) . . ?
P2 Se2 I2 94.01(6) . . ?
P3 Se3 I4 94.74(6) . . ?
P4 Se4 I5 93.10(6) . . ?
C21 P1 C11 106.0(4) . . ?
C21 P1 C01 103.1(4) . . ?
C11 P1 C01 108.4(4) . . ?
C21 P1 Se1 116.9(3) . . ?
C11 P1 Se1 106.3(3) . . ?
C01 P1 Se1 115.6(3) . . ?
C41 P2 C31 109.9(4) . . ?
C41 P2 C01 104.2(4) . . ?
C31 P2 C01 110.2(4) . . ?
C41 P2 Se2 113.0(3) . . ?
C31 P2 Se2 111.5(3) . . ?
C01 P2 Se2 107.8(3) . . ?
C61 P3 C51 107.5(4) . . ?
C61 P3 C02 107.1(4) . . ?
C51 P3 C02 103.8(3) . . ?
C61 P3 Se3 113.9(3) . . ?
C51 P3 Se3 114.0(3) . . ?
C02 P3 Se3 109.9(3) . . ?
C71 P4 C81 109.7(4) . . ?
C71 P4 C02 110.4(4) . . ?
C81 P4 C02 102.8(4) . . ?
C71 P4 Se4 112.0(3) . . ?
C81 P4 Se4 112.2(3) . . ?
C02 P4 Se4 109.4(3) . . ?
P1 C01 P2 119.9(4) . . ?
P3 C02 P4 119.9(4) . . ?
C16 C11 C12 120.1(7) . . ?
C16 C11 P1 120.2(6) . . ?
C12 C11 P1 119.6(6) . . ?
C13 C12 C11 119.6(7) . . ?
C14 C13 C12 119.6(8) . . ?
C15 C14 C13 121.5(8) . . ?
C14 C15 C16 119.1(8) . . ?
C11 C16 C15 120.1(8) . . ?
C22 C21 C26 118.5(7) . . ?
C22 C21 P1 121.0(6) . . ?
C26 C21 P1 120.5(6) . . ?
C21 C22 C23 121.1(8) . . ?
C24 C23 C22 120.5(8) . . ?
C23 C24 C25 119.4(8) . . ?
C26 C25 C24 120.1(8) . . ?
C25 C26 C21 120.3(8) . . ?
C36 C31 C32 120.6(7) . . ?
C36 C31 P2 119.2(6) . . ?
C32 C31 P2 120.1(6) . . ?
C31 C32 C33 118.7(7) . . ?
C34 C33 C32 120.8(8) . . ?
C33 C34 C35 120.9(8) . . ?
C36 C35 C34 117.7(8) . . ?
C31 C36 C35 121.1(8) . . ?
C46 C41 C42 119.4(7) . . ?
C46 C41 P2 121.4(6) . . ?
C42 C41 P2 119.0(6) . . ?
C43 C42 C41 120.0(7) . . ?
C44 C43 C42 119.7(8) . . ?
C43 C44 C45 120.9(9) . . ?
C44 C45 C46 120.2(8) . . ?
C41 C46 C45 119.8(8) . . ?
C56 C51 C52 119.7(7) . . ?
C56 C51 P3 120.6(6) . . ?
C52 C51 P3 119.7(6) . . ?
C51 C52 C53 119.8(7) . . ?
C54 C53 C52 120.1(8) . . ?
C55 C54 C53 118.8(8) . . ?
C56 C55 C54 121.3(8) . . ?
C55 C56 C51 120.3(8) . . ?
C62 C61 C66 119.5(7) . . ?
C62 C61 P3 120.2(6) . . ?
C66 C61 P3 120.3(6) . . ?
C63 C62 C61 119.5(7) . . ?
C62 C63 C64 121.3(7) . . ?
C65 C64 C63 118.5(8) . . ?
C64 C65 C66 122.4(8) . . ?
C65 C66 C61 118.8(7) . . ?
C72 C71 C76 120.1(7) . . ?
C72 C71 P4 120.0(6) . . ?
C76 C71 P4 119.8(6) . . ?
C73 C72 C71 120.0(8) . . ?
C72 C73 C74 121.4(8) . . ?
C73 C74 C75 118.7(8) . . ?
C76 C75 C74 120.0(8) . . ?
C75 C76 C71 119.7(8) . . ?
C86 C81 C82 119.7(7) . . ?
C86 C81 P4 120.1(6) . . ?
C82 C81 P4 120.2(6) . . ?
C83 C82 C81 118.9(8) . . ?
C82 C83 C84 121.8(9) . . ?
C83 C84 C85 119.3(8) . . ?
C84 C85 C86 119.4(8) . . ?
C81 C86 C85 120.9(8) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
I1 Se1 P1 C21 -58.5(3) . . . . ?
I1 Se1 P1 C11 -176.5(3) . . . . ?
I1 Se1 P1 C01 63.1(3) . . . . ?
I2 Se2 P2 C41 -55.3(3) . . . . ?
I2 Se2 P2 C31 69.0(3) . . . . ?
I2 Se2 P2 C01 -169.9(3) . . . . ?
I4 Se3 P3 C61 63.1(3) . . . . ?
I4 Se3 P3 C51 -60.7(3) . . . . ?
I4 Se3 P3 C02 -176.8(3) . . . . ?
I5 Se4 P4 C71 -67.9(3) . . . . ?
I5 Se4 P4 C81 55.9(3) . . . . ?
I5 Se4 P4 C02 169.4(3) . . . . ?
C21 P1 C01 P2 179.2(5) . . . . ?
C11 P1 C01 P2 -68.8(6) . . . . ?
Se1 P1 C01 P2 50.4(5) . . . . ?
C41 P2 C01 P1 153.0(5) . . . . ?
C31 P2 C01 P1 35.2(6) . . . . ?
Se2 P2 C01 P1 -86.7(5) . . . . ?
C61 P3 C02 P4 71.3(5) . . . . ?
C51 P3 C02 P4 -175.2(5) . . . . ?
Se3 P3 C02 P4 -52.9(5) . . . . ?
C71 P4 C02 P3 -42.3(6) . . . . ?
C81 P4 C02 P3 -159.2(5) . . . . ?
Se4 P4 C02 P3 81.4(5) . . . . ?
C21 P1 C11 C16 -121.2(7) . . . . ?
C01 P1 C11 C16 128.7(7) . . . . ?
Se1 P1 C11 C16 3.8(7) . . . . ?
C21 P1 C11 C12 56.6(7) . . . . ?
C01 P1 C11 C12 -53.5(7) . . . . ?
Se1 P1 C11 C12 -178.4(6) . . . . ?
C16 C11 C12 C13 -1.0(12) . . . . ?
P1 C11 C12 C13 -178.8(6) . . . . ?
C11 C12 C13 C14 -0.1(12) . . . . ?
C12 C13 C14 C15 0.7(13) . . . . ?
C13 C14 C15 C16 -0.2(13) . . . . ?
C12 C11 C16 C15 1.4(12) . . . . ?
P1 C11 C16 C15 179.2(6) . . . . ?
C14 C15 C16 C11 -0.8(13) . . . . ?
C11 P1 C21 C22 25.3(7) . . . . ?
C01 P1 C21 C22 139.1(7) . . . . ?
Se1 P1 C21 C22 -92.9(7) . . . . ?
C11 P1 C21 C26 -155.6(6) . . . . ?
C01 P1 C21 C26 -41.8(7) . . . . ?
Se1 P1 C21 C26 86.2(7) . . . . ?
C26 C21 C22 C23 3.2(12) . . . . ?
P1 C21 C22 C23 -177.7(6) . . . . ?
C21 C22 C23 C24 -0.2(12) . . . . ?
C22 C23 C24 C25 -3.0(13) . . . . ?
C23 C24 C25 C26 3.0(13) . . . . ?
C24 C25 C26 C21 0.1(13) . . . . ?
C22 C21 C26 C25 -3.1(12) . . . . ?
P1 C21 C26 C25 177.7(6) . . . . ?
C41 P2 C31 C36 143.7(7) . . . . ?
C01 P2 C31 C36 -102.0(7) . . . . ?
Se2 P2 C31 C36 17.7(7) . . . . ?
C41 P2 C31 C32 -39.1(7) . . . . ?
C01 P2 C31 C32 75.3(7) . . . . ?
Se2 P2 C31 C32 -165.1(6) . . . . ?
C36 C31 C32 C33 -0.4(12) . . . . ?
P2 C31 C32 C33 -177.6(6) . . . . ?
C31 C32 C33 C34 0.9(13) . . . . ?
C32 C33 C34 C35 0.6(13) . . . . ?
C33 C34 C35 C36 -2.4(13) . . . . ?
C32 C31 C36 C35 -1.6(13) . . . . ?
P2 C31 C36 C35 175.7(7) . . . . ?
C34 C35 C36 C31 2.9(13) . . . . ?
C31 P2 C41 C46 -29.9(7) . . . . ?
C01 P2 C41 C46 -148.0(6) . . . . ?
Se2 P2 C41 C46 95.2(6) . . . . ?
C31 P2 C41 C42 154.6(6) . . . . ?
C01 P2 C41 C42 36.5(7) . . . . ?
Se2 P2 C41 C42 -80.2(6) . . . . ?
C46 C41 C42 C43 2.4(11) . . . . ?
P2 C41 C42 C43 178.0(6) . . . . ?
C41 C42 C43 C44 -2.4(12) . . . . ?
C42 C43 C44 C45 1.9(13) . . . . ?
C43 C44 C45 C46 -1.4(13) . . . . ?
C42 C41 C46 C45 -1.9(11) . . . . ?
P2 C41 C46 C45 -177.4(6) . . . . ?
C44 C45 C46 C41 1.4(13) . . . . ?
C61 P3 C51 C56 -24.1(8) . . . . ?
C02 P3 C51 C56 -137.3(7) . . . . ?
Se3 P3 C51 C56 103.1(6) . . . . ?
C61 P3 C51 C52 157.7(6) . . . . ?
C02 P3 C51 C52 44.5(7) . . . . ?
Se3 P3 C51 C52 -75.1(7) . . . . ?
C56 C51 C52 C53 1.4(12) . . . . ?
P3 C51 C52 C53 179.6(6) . . . . ?
C51 C52 C53 C54 0.1(12) . . . . ?
C52 C53 C54 C55 -1.5(12) . . . . ?
C53 C54 C55 C56 1.5(12) . . . . ?
C54 C55 C56 C51 0.0(12) . . . . ?
C52 C51 C56 C55 -1.4(12) . . . . ?
P3 C51 C56 C55 -179.6(6) . . . . ?
C51 P3 C61 C62 127.2(6) . . . . ?
C02 P3 C61 C62 -121.8(6) . . . . ?
Se3 P3 C61 C62 0.0(7) . . . . ?
C51 P3 C61 C66 -54.2(7) . . . . ?
C02 P3 C61 C66 56.8(7) . . . . ?
Se3 P3 C61 C66 178.5(5) . . . . ?
C66 C61 C62 C63 2.0(11) . . . . ?
P3 C61 C62 C63 -179.4(6) . . . . ?
C61 C62 C63 C64 -2.6(12) . . . . ?
C62 C63 C64 C65 1.7(12) . . . . ?
C63 C64 C65 C66 -0.3(12) . . . . ?
C64 C65 C66 C61 -0.3(12) . . . . ?
C62 C61 C66 C65 -0.6(11) . . . . ?
P3 C61 C66 C65 -179.2(6) . . . . ?
C81 P4 C71 C72 -141.5(6) . . . . ?
C02 P4 C71 C72 105.9(7) . . . . ?
Se4 P4 C71 C72 -16.3(7) . . . . ?
C81 P4 C71 C76 42.0(7) . . . . ?
C02 P4 C71 C76 -70.6(7) . . . . ?
Se4 P4 C71 C76 167.3(6) . . . . ?
C76 C71 C72 C73 -0.4(12) . . . . ?
P4 C71 C72 C73 -176.9(6) . . . . ?
C71 C72 C73 C74 0.6(13) . . . . ?
C72 C73 C74 C75 -1.8(13) . . . . ?
C73 C74 C75 C76 2.7(12) . . . . ?
C74 C75 C76 C71 -2.6(12) . . . . ?
C72 C71 C76 C75 1.4(12) . . . . ?
P4 C71 C76 C75 177.9(6) . . . . ?
C71 P4 C81 C86 -154.4(6) . . . . ?
C02 P4 C81 C86 -36.9(7) . . . . ?
Se4 P4 C81 C86 80.5(7) . . . . ?
C71 P4 C81 C82 27.1(8) . . . . ?
C02 P4 C81 C82 144.5(7) . . . . ?
Se4 P4 C81 C82 -98.1(6) . . . . ?
C86 C81 C82 C83 -0.1(12) . . . . ?
P4 C81 C82 C83 178.4(6) . . . . ?
C81 C82 C83 C84 0.8(13) . . . . ?
C82 C83 C84 C85 -0.5(13) . . . . ?
C83 C84 C85 C86 -0.4(13) . . . . ?
C82 C81 C86 C85 -0.8(12) . . . . ?
P4 C81 C86 C85 -179.4(6) . . . . ?
C84 C85 C86 C81 1.1(13) . . . . ?

_diffrn_measured_fraction_theta_max 0.985
_diffrn_reflns_theta_full        30.03
_diffrn_measured_fraction_theta_full 0.985
_refine_diff_density_max         2.112
_refine_diff_density_min         -2.355
_refine_diff_density_rms         0.251


# end of cif file
####################################################################### 
# 
# 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_chris
_database_code_depnum_ccdc_archive 'CCDC 1496348'
_audit_update_record             
;
2016-07-27 deposited with the CCDC.
2018-02-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C50 H46 Br8 O4 P4 Se3'
_chemical_formula_weight         1710.91

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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.4803(5)
_cell_length_b                   11.8359(8)
_cell_length_c                   12.1607(6)
_cell_angle_alpha                68.775(6)
_cell_angle_beta                 85.723(4)
_cell_angle_gamma                86.800(5)
_cell_volume                     1401.54(14)
_cell_formula_units_Z            1
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    7525
_cell_measurement_theta_min      2.5640
_cell_measurement_theta_max      25.4810

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_diffrn    2.027
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             820
_exptl_absorpt_coefficient_mu    7.827
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.71151
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur, Eos'
_diffrn_measurement_method       'ω scan'
_diffrn_detector_area_resol_mean 16.1419
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            68560
_diffrn_reflns_av_R_equivalents  0.0824
_diffrn_reflns_av_sigmaI/netI    0.0464
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.58
_diffrn_reflns_theta_max         27.88
_reflns_number_total             6684
_reflns_number_gt                5301
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker XP'
_computing_publication_material  SHEXL-97

_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.

 The OH hydrogen atom was refined freely, but with an O-H distance
 restraint (DFIX).
;

_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)+(0.0290P)²+4.8083P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         6684
_refine_ls_number_parameters     317
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0607
_refine_ls_R_factor_gt           0.0420
_refine_ls_wR_factor_ref         0.0907
_refine_ls_wR_factor_gt          0.0841
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_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
Se1 Se 0.5000 0.5000 0.5000 0.01584(14) Uani 1 2 d S . .
Br1 Br 0.50883(5) 0.29696(4) 0.46238(4) 0.02173(11) Uani 1 1 d . . .
Br2 Br 0.38702(4) 0.59922(4) 0.30315(4) 0.01916(11) Uani 1 1 d . . .
Se2 Se 0.37376(5) 0.84922(4) 0.31964(4) 0.02162(12) Uani 1 1 d . . .
Br3 Br 0.28338(5) 0.93763(4) 0.13195(4) 0.02525(12) Uani 1 1 d . . .
Br4 Br 0.40059(5) 1.02774(5) 0.35811(4) 0.02659(12) Uani 1 1 d . . .
P1 P 0.88289(10) 0.54215(10) 0.19463(9) 0.0110(2) Uani 1 1 d . . .
P2 P 0.74758(10) 0.37128(10) 0.11270(9) 0.0108(2) Uani 1 1 d . . .
O1 O 0.9705(3) 0.5427(3) 0.0905(3) 0.0154(6) Uani 1 1 d . . .
O2 O 0.8081(3) 0.4212(3) -0.0135(3) 0.0138(6) Uani 1 1 d D . .
H01 H 0.905(2) 0.434(7) -0.039(6) 0.08(2) Uiso 1 1 d D . .
C01 C 0.7303(4) 0.4829(4) 0.1821(4) 0.0122(8) Uani 1 1 d . . .
H01A H 0.6882 0.4458 0.2620 0.015 Uiso 1 1 calc R . .
H01B H 0.6742 0.5507 0.1356 0.015 Uiso 1 1 calc R . .
C11 C 0.8511(4) 0.6936(4) 0.1905(4) 0.0129(8) Uani 1 1 d . . .
C12 C 0.9520(4) 0.7738(4) 0.1481(4) 0.0186(10) Uani 1 1 d . . .
H12 H 1.0333 0.7457 0.1267 0.022 Uiso 1 1 calc R . .
C13 C 0.9337(5) 0.8933(4) 0.1375(4) 0.0240(11) Uani 1 1 d . . .
H13 H 1.0022 0.9476 0.1086 0.029 Uiso 1 1 calc R . .
C14 C 0.8158(5) 0.9343(4) 0.1687(4) 0.0228(11) Uani 1 1 d . . .
H14 H 0.8027 1.0171 0.1597 0.027 Uiso 1 1 calc R . .
C15 C 0.7171(5) 0.8552(5) 0.2129(5) 0.0254(11) Uani 1 1 d . . .
H15 H 0.6366 0.8842 0.2351 0.031 Uiso 1 1 calc R . .
C16 C 0.7331(4) 0.7342(4) 0.2257(4) 0.0190(10) Uani 1 1 d . . .
H16 H 0.6649 0.6799 0.2578 0.023 Uiso 1 1 calc R . .
C21 C 0.9475(4) 0.4478(4) 0.3305(4) 0.0119(8) Uani 1 1 d . . .
C22 C 0.8751(4) 0.4076(5) 0.4378(4) 0.0218(10) Uani 1 1 d . . .
H22 H 0.7873 0.4315 0.4411 0.026 Uiso 1 1 calc R . .
C23 C 0.9312(5) 0.3331(5) 0.5388(4) 0.0254(11) Uani 1 1 d . . .
H23 H 0.8818 0.3058 0.6118 0.031 Uiso 1 1 calc R . .
C24 C 1.0582(5) 0.2978(4) 0.5348(4) 0.0218(10) Uani 1 1 d . . .
H24 H 1.0952 0.2439 0.6042 0.026 Uiso 1 1 calc R . .
C25 C 1.1322(5) 0.3406(5) 0.4302(4) 0.0289(12) Uani 1 1 d . . .
H25 H 1.2208 0.3189 0.4285 0.035 Uiso 1 1 calc R . .
C26 C 1.0773(4) 0.4149(5) 0.3280(4) 0.0245(11) Uani 1 1 d . . .
H26 H 1.1280 0.4437 0.2558 0.029 Uiso 1 1 calc R . .
C31 C 0.5919(4) 0.3269(4) 0.0997(4) 0.0116(8) Uani 1 1 d . . .
C32 C 0.4796(4) 0.3650(4) 0.1477(4) 0.0146(9) Uani 1 1 d . . .
H32 H 0.4835 0.4160 0.1923 0.018 Uiso 1 1 calc R . .
C33 C 0.3630(4) 0.3277(4) 0.1297(4) 0.0179(9) Uani 1 1 d . . .
H33 H 0.2865 0.3535 0.1619 0.021 Uiso 1 1 calc R . .
C34 C 0.3565(4) 0.2532(4) 0.0652(4) 0.0181(10) Uani 1 1 d . . .
H34 H 0.2758 0.2273 0.0544 0.022 Uiso 1 1 calc R . .
C35 C 0.4672(4) 0.2162(4) 0.0164(4) 0.0198(10) Uani 1 1 d . . .
H35 H 0.4623 0.1659 -0.0287 0.024 Uiso 1 1 calc R . .
C36 C 0.5849(4) 0.2526(4) 0.0334(4) 0.0177(9) Uani 1 1 d . . .
H36 H 0.6609 0.2271 0.0002 0.021 Uiso 1 1 calc R . .
C41 C 0.8374(4) 0.2440(4) 0.2038(4) 0.0120(8) Uani 1 1 d . . .
C42 C 0.7791(4) 0.1616(4) 0.3066(4) 0.0181(9) Uani 1 1 d . . .
H42 H 0.6912 0.1726 0.3271 0.022 Uiso 1 1 calc R . .
C43 C 0.8499(5) 0.0639(4) 0.3786(4) 0.0221(10) Uani 1 1 d . . .
H43 H 0.8106 0.0080 0.4486 0.027 Uiso 1 1 calc R . .
C44 C 0.9784(4) 0.0475(4) 0.3485(4) 0.0181(10) Uani 1 1 d . . .
H44 H 1.0265 -0.0201 0.3974 0.022 Uiso 1 1 calc R . .
C45 C 1.0362(4) 0.1293(4) 0.2474(4) 0.0185(9) Uani 1 1 d . . .
H45 H 1.1242 0.1180 0.2277 0.022 Uiso 1 1 calc R . .
C46 C 0.9673(4) 0.2274(4) 0.1747(4) 0.0167(9) Uani 1 1 d . . .
H46 H 1.0077 0.2832 0.1053 0.020 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
Se1 Br2 2.5968(5) 2_666 ?
Se1 Br2 2.5968(5) . ?
Se1 Br1 2.5996(5) . ?
Se1 Br1 2.5996(5) 2_666 ?
Br2 Se2 3.0323(7) . ?
Se2 Br4 2.3588(7) . ?
Se2 Br3 2.3841(7) . ?
Se2 Br1 2.9090(7) 2_666 ?
P1 O1 1.505(3) . ?
P1 C21 1.784(4) . ?
P1 C11 1.788(4) . ?
P1 C01 1.820(4) . ?
P2 O2 1.531(3) . ?
P2 C31 1.777(4) . ?
P2 C41 1.781(4) . ?
P2 C01 1.802(4) . ?
C11 C16 1.396(6) . ?
C11 C12 1.401(6) . ?
C12 C13 1.376(7) . ?
C13 C14 1.379(7) . ?
C14 C15 1.376(7) . ?
C15 C16 1.386(6) . ?
C21 C22 1.395(6) . ?
C21 C26 1.396(6) . ?
C22 C23 1.378(6) . ?
C23 C24 1.375(7) . ?
C24 C25 1.380(7) . ?
C25 C26 1.382(7) . ?
C31 C32 1.399(6) . ?
C31 C36 1.400(6) . ?
C32 C33 1.381(6) . ?
C33 C34 1.382(6) . ?
C34 C35 1.385(6) . ?
C35 C36 1.383(6) . ?
C41 C42 1.399(6) . ?
C41 C46 1.403(6) . ?
C42 C43 1.387(6) . ?
C43 C44 1.391(7) . ?
C44 C45 1.381(6) . ?
C45 C46 1.382(6) . ?

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
Br2 Se1 Br2 180.0 2_666 . ?
Br2 Se1 Br1 92.041(15) 2_666 . ?
Br2 Se1 Br1 87.959(15) . . ?
Br2 Se1 Br1 87.959(16) 2_666 2_666 ?
Br2 Se1 Br1 92.041(15) . 2_666 ?
Br1 Se1 Br1 180.0 . 2_666 ?
Se1 Br2 Se2 93.516(17) . . ?
Br4 Se2 Br3 98.88(3) . . ?
Br4 Se2 Br1 90.99(2) . 2_666 ?
Br3 Se2 Br1 169.79(3) . 2_666 ?
Br4 Se2 Br2 167.79(3) . . ?
Br3 Se2 Br2 91.95(2) . . ?
Br1 Se2 Br2 77.975(18) 2_666 . ?
O1 P1 C21 111.18(19) . . ?
O1 P1 C11 110.27(19) . . ?
C21 P1 C11 111.55(19) . . ?
O1 P1 C01 108.17(18) . . ?
C21 P1 C01 108.68(19) . . ?
C11 P1 C01 106.8(2) . . ?
O2 P2 C31 105.73(18) . . ?
O2 P2 C41 111.44(18) . . ?
C31 P2 C41 109.95(19) . . ?
O2 P2 C01 113.08(18) . . ?
C31 P2 C01 107.9(2) . . ?
C41 P2 C01 108.65(19) . . ?
P2 C01 P1 112.6(2) . . ?
C16 C11 C12 119.8(4) . . ?
C16 C11 P1 123.6(3) . . ?
C12 C11 P1 116.6(3) . . ?
C13 C12 C11 120.2(4) . . ?
C12 C13 C14 120.0(4) . . ?
C15 C14 C13 120.1(4) . . ?
C14 C15 C16 121.2(5) . . ?
C15 C16 C11 118.7(4) . . ?
C22 C21 C26 119.3(4) . . ?
C22 C21 P1 123.2(3) . . ?
C26 C21 P1 117.5(3) . . ?
C23 C22 C21 119.9(4) . . ?
C24 C23 C22 120.5(4) . . ?
C23 C24 C25 120.3(4) . . ?
C24 C25 C26 119.9(4) . . ?
C25 C26 C21 120.1(4) . . ?
C32 C31 C36 119.9(4) . . ?
C32 C31 P2 124.0(3) . . ?
C36 C31 P2 116.1(3) . . ?
C33 C32 C31 119.3(4) . . ?
C32 C33 C34 120.7(4) . . ?
C33 C34 C35 120.3(4) . . ?
C36 C35 C34 119.9(4) . . ?
C35 C36 C31 119.9(4) . . ?
C42 C41 C46 119.7(4) . . ?
C42 C41 P2 120.0(3) . . ?
C46 C41 P2 120.4(3) . . ?
C43 C42 C41 119.8(4) . . ?
C42 C43 C44 120.1(4) . . ?
C45 C44 C43 120.1(4) . . ?
C44 C45 C46 120.7(4) . . ?
C45 C46 C41 119.7(4) . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        27.88
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         1.049
_refine_diff_density_min         -1.013
_refine_diff_density_rms         0.140


# start Validation Reply Form
_vrf_PLAT431_chris               
;
PROBLEM: Short Inter HL..A Contact Br1 .. Se2 .. 2.91 Ang.
RESPONSE: These are genuine short contacts (or long bonds).
;
# end Validation Reply Form

# end of cif file
####################################################################### 
# 
# 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_monty
_database_code_depnum_ccdc_archive 'CCDC 1494783'
_audit_update_record             
;
2016-07-19 deposited with the CCDC.
2018-02-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C38 H36 Br4 P2 Se2'
_chemical_formula_weight         1032.16

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'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.7943 1.1372 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.6763 1.2805 '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/c'

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

_cell_length_a                   11.2185(2)
_cell_length_b                   6.7500(2)
_cell_length_c                   24.9397(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 93.656(2)
_cell_angle_gamma                90.00
_cell_volume                     1884.72(8)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    16243
_cell_measurement_theta_min      3.9300
_cell_measurement_theta_max      76.0660

_exptl_crystal_description       lath
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.819
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1004
_exptl_absorpt_coefficient_mu    8.426
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.29393
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           'Cu K\a'
_diffrn_source                   'sealed X-ray tube'
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur, Atlas, Nova'
_diffrn_measurement_method       'ω scan'
_diffrn_detector_area_resol_mean 10.3543
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            36988
_diffrn_reflns_av_R_equivalents  0.0687
_diffrn_reflns_av_sigmaI/netI    0.0269
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         3.55
_diffrn_reflns_theta_max         76.34
_reflns_number_total             3942
_reflns_number_gt                3634
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker XP'
_computing_publication_material  SHEXL-97

_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)+(0.0378P)²+2.3074P] 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_number_reflns         3942
_refine_ls_number_parameters     208
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0325
_refine_ls_R_factor_gt           0.0292
_refine_ls_wR_factor_ref         0.0759
_refine_ls_wR_factor_gt          0.0737
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_restrained_S_all      1.075
_refine_ls_shift/su_max          0.002
_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
Br1 Br 0.76987(3) 0.15116(4) 0.360840(12) 0.02401(9) Uani 1 1 d . . .
Br2 Br 0.64357(3) 0.09797(4) 0.554389(11) 0.02118(9) Uani 1 1 d . . .
Se1 Se 0.69684(2) 0.13022(4) 0.456195(11) 0.01729(9) Uani 1 1 d . . .
P1 P 0.65324(5) 0.45497(9) 0.44888(2) 0.01289(13) Uani 1 1 d . . .
C1 C 0.5640(2) 0.5416(4) 0.50260(10) 0.0143(5) Uani 1 1 d . . .
H1A H 0.6029 0.5008 0.5376 0.017 Uiso 1 1 calc R . .
H1B H 0.5608 0.6881 0.5019 0.017 Uiso 1 1 calc R . .
C11 C 0.7904(2) 0.5918(4) 0.45388(10) 0.0146(5) Uani 1 1 d . . .
C12 C 0.8385(2) 0.6553(4) 0.50423(11) 0.0172(5) Uani 1 1 d . . .
H12 H 0.7951 0.6379 0.5354 0.021 Uiso 1 1 calc R . .
C13 C 0.9506(2) 0.7439(4) 0.50804(11) 0.0202(5) Uani 1 1 d . . .
H13 H 0.9845 0.7860 0.5420 0.024 Uiso 1 1 calc R . .
C14 C 1.0131(2) 0.7712(4) 0.46247(12) 0.0210(5) Uani 1 1 d . . .
H14 H 1.0896 0.8321 0.4655 0.025 Uiso 1 1 calc R . .
C15 C 0.9652(2) 0.7107(4) 0.41245(12) 0.0206(5) Uani 1 1 d . . .
H15 H 1.0081 0.7321 0.3813 0.025 Uiso 1 1 calc R . .
C16 C 0.8541(2) 0.6186(4) 0.40804(11) 0.0184(5) Uani 1 1 d . . .
H16 H 0.8217 0.5740 0.3740 0.022 Uiso 1 1 calc R . .
C21 C 0.5688(2) 0.5062(4) 0.38683(10) 0.0149(5) Uani 1 1 d . . .
C22 C 0.5771(2) 0.6928(4) 0.36328(11) 0.0189(5) Uani 1 1 d . . .
H22 H 0.6316 0.7884 0.3784 0.023 Uiso 1 1 calc R . .
C23 C 0.5049(3) 0.7376(5) 0.31751(11) 0.0236(6) Uani 1 1 d . . .
H23 H 0.5109 0.8635 0.3009 0.028 Uiso 1 1 calc R . .
C24 C 0.4241(3) 0.5991(5) 0.29606(11) 0.0259(6) Uani 1 1 d . . .
H24 H 0.3748 0.6306 0.2648 0.031 Uiso 1 1 calc R . .
C25 C 0.4149(3) 0.4141(5) 0.32006(12) 0.0271(6) Uani 1 1 d . . .
H25 H 0.3589 0.3202 0.3053 0.032 Uiso 1 1 calc R . .
C26 C 0.4870(2) 0.3660(4) 0.36542(11) 0.0204(5) Uani 1 1 d . . .
H26 H 0.4810 0.2395 0.3818 0.024 Uiso 1 1 calc R . .
C91 C 0.7924(3) -0.0583(5) 0.74648(13) 0.0273(6) Uani 1 1 d . . .
H91 H 0.7499 0.0233 0.7697 0.033 Uiso 1 1 calc R . .
C92 C 0.8096(3) 0.0048(5) 0.69479(13) 0.0262(6) Uani 1 1 d . . .
H92 H 0.7793 0.1292 0.6824 0.031 Uiso 1 1 calc R . .
C93 C 0.8721(3) -0.1168(5) 0.66113(14) 0.0318(7) Uani 1 1 d . . .
H93 H 0.8832 -0.0762 0.6253 0.038 Uiso 1 1 calc R . .
C94 C 0.9180(3) -0.2956(5) 0.67955(16) 0.0362(8) Uani 1 1 d . . .
H94 H 0.9621 -0.3761 0.6567 0.043 Uiso 1 1 calc R . .
C95 C 0.8997(3) -0.3585(5) 0.73146(15) 0.0316(7) Uani 1 1 d . . .
H95 H 0.9303 -0.4824 0.7441 0.038 Uiso 1 1 calc R . .
C96 C 0.8366(3) -0.2389(5) 0.76456(12) 0.0284(6) Uani 1 1 d . . .
H96 H 0.8234 -0.2812 0.8000 0.034 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
Br1 Se1 2.5681(4) . ?
Br2 Se1 2.5668(4) . ?
Se1 P1 2.2509(7) . ?
P1 C11 1.792(3) . ?
P1 C21 1.796(3) . ?
P1 C1 1.819(2) . ?
C1 C1 1.540(5) 3_666 ?
C11 C16 1.398(4) . ?
C11 C12 1.402(4) . ?
C12 C13 1.390(4) . ?
C13 C14 1.385(4) . ?
C14 C15 1.388(4) . ?
C15 C16 1.390(4) . ?
C21 C22 1.395(4) . ?
C21 C26 1.401(4) . ?
C22 C23 1.391(4) . ?
C23 C24 1.385(4) . ?
C24 C25 1.391(5) . ?
C25 C26 1.387(4) . ?
C91 C96 1.381(5) . ?
C91 C92 1.383(4) . ?
C92 C93 1.395(5) . ?
C93 C94 1.379(5) . ?
C94 C95 1.390(5) . ?
C95 C96 1.382(5) . ?

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
P1 Se1 Br2 95.58(2) . . ?
P1 Se1 Br1 87.240(19) . . ?
Br2 Se1 Br1 174.626(15) . . ?
C11 P1 C21 111.34(12) . . ?
C11 P1 C1 107.06(12) . . ?
C21 P1 C1 106.75(11) . . ?
C11 P1 Se1 108.37(8) . . ?
C21 P1 Se1 110.95(9) . . ?
C1 P1 Se1 112.34(9) . . ?
C1 C1 P1 112.0(2) 3_666 . ?
C16 C11 C12 120.4(2) . . ?
C16 C11 P1 119.4(2) . . ?
C12 C11 P1 120.0(2) . . ?
C13 C12 C11 119.2(3) . . ?
C14 C13 C12 120.3(3) . . ?
C13 C14 C15 120.7(2) . . ?
C14 C15 C16 119.8(3) . . ?
C15 C16 C11 119.7(3) . . ?
C22 C21 C26 120.6(2) . . ?
C22 C21 P1 119.4(2) . . ?
C26 C21 P1 119.7(2) . . ?
C23 C22 C21 119.4(3) . . ?
C24 C23 C22 120.2(3) . . ?
C23 C24 C25 120.3(3) . . ?
C26 C25 C24 120.4(3) . . ?
C25 C26 C21 119.1(3) . . ?
C96 C91 C92 120.5(3) . . ?
C91 C92 C93 119.0(3) . . ?
C94 C93 C92 120.4(3) . . ?
C93 C94 C95 120.2(3) . . ?
C96 C95 C94 119.3(3) . . ?
C91 C96 C95 120.5(3) . . ?

_diffrn_measured_fraction_theta_max 0.996
_diffrn_reflns_theta_full        75.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.577
_refine_diff_density_min         -0.792
_refine_diff_density_rms         0.102


# end of cif file
####################################################################### 
# 
# 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_gisela
_database_code_depnum_ccdc_archive 'CCDC 1579323'
_audit_update_record             
;
2017-10-11 deposited with the CCDC.
2018-02-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H24 P2 Se2'
_chemical_formula_weight         556.31

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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.0929 2.2259 '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/n'

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

_cell_length_a                   9.5936(2)
_cell_length_b                   16.1956(3)
_cell_length_c                   15.7995(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 103.381(2)
_cell_angle_gamma                90.00
_cell_volume                     2388.21(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    30186
_cell_measurement_theta_min      2.1777
_cell_measurement_theta_max      30.8115

_exptl_crystal_description       lath
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.04
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.547
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1112
_exptl_absorpt_coefficient_mu    3.242
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.73535
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
; 
CrysAlisPro, Oxford Diffraction Ltd., 
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) 
(compiled Jan 23 2012,18:06:46) 
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur, Eos'
_diffrn_measurement_method       ω-scan
_diffrn_detector_area_resol_mean 16.1419
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            151754
_diffrn_reflns_av_R_equivalents  0.0495
_diffrn_reflns_av_sigmaI/netI    0.0195
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.28
_diffrn_reflns_theta_max         30.03
_reflns_number_total             6977
_reflns_number_gt                6115
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
; 
CrysAlisPro, Oxford Diffraction Ltd., 
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) 
(compiled Jan 23 2012,18:06:46) 
;
_computing_cell_refinement       
; 
CrysAlisPro, Oxford Diffraction Ltd., 
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) 
(compiled Jan 23 2012,18:06:46) 
;
_computing_data_reduction        
; 
CrysAlisPro, Oxford Diffraction Ltd., 
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) 
(compiled Jan 23 2012,18:06:46) 
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker XP'
_computing_publication_material  SHELXL-97

_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)+(0.0244P)²+1.9514P] 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_number_reflns         6977
_refine_ls_number_parameters     271
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0348
_refine_ls_R_factor_gt           0.0264
_refine_ls_wR_factor_ref         0.0580
_refine_ls_wR_factor_gt          0.0553
_refine_ls_goodness_of_fit_ref   1.036
_refine_ls_restrained_S_all      1.036
_refine_ls_shift/su_max          0.002
_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
P1 P 0.63918(4) 0.70292(2) 0.61079(2) 0.01217(8) Uani 1 1 d . . .
P2 P 0.75022(4) 0.84841(2) 0.39867(2) 0.01151(7) Uani 1 1 d . . .
Se1 Se 0.806900(18) 0.617115(10) 0.620470(11) 0.01887(4) Uani 1 1 d . . .
Se2 Se 0.586295(17) 0.936307(10) 0.358031(11) 0.01905(4) Uani 1 1 d . . .
C1 C 0.61702(17) 0.76558(10) 0.51247(10) 0.0147(3) Uani 1 1 d . . .
H1A H 0.5839 0.7301 0.4607 0.018 Uiso 1 1 calc R . .
H1B H 0.5428 0.8081 0.5123 0.018 Uiso 1 1 calc R . .
C2 C 0.75756(17) 0.80775(10) 0.50705(10) 0.0152(3) Uani 1 1 d . . .
H2A H 0.8370 0.7675 0.5225 0.018 Uiso 1 1 calc R . .
H2B H 0.7776 0.8534 0.5498 0.018 Uiso 1 1 calc R . .
C11 C 0.46411(17) 0.65632(10) 0.60285(9) 0.0144(3) Uani 1 1 d . . .
C12 C 0.44629(18) 0.57150(10) 0.58828(10) 0.0184(3) Uani 1 1 d . . .
H12 H 0.5259 0.5383 0.5838 0.022 Uiso 1 1 calc R . .
C13 C 0.3119(2) 0.53557(12) 0.58031(11) 0.0236(4) Uani 1 1 d . . .
H13 H 0.2999 0.4778 0.5706 0.028 Uiso 1 1 calc R . .
C14 C 0.1959(2) 0.58428(13) 0.58654(12) 0.0264(4) Uani 1 1 d . . .
H14 H 0.1043 0.5598 0.5811 0.032 Uiso 1 1 calc R . .
C15 C 0.21277(19) 0.66872(12) 0.60069(11) 0.0239(4) Uani 1 1 d . . .
H15 H 0.1325 0.7018 0.6043 0.029 Uiso 1 1 calc R . .
C16 C 0.34683(18) 0.70503(11) 0.60966(10) 0.0188(3) Uani 1 1 d . . .
H16 H 0.3586 0.7626 0.6204 0.023 Uiso 1 1 calc R . .
C21 C 0.66961(16) 0.77442(9) 0.70169(10) 0.0131(3) Uani 1 1 d . . .
C22 C 0.72888(17) 0.74327(11) 0.78485(10) 0.0175(3) Uani 1 1 d . . .
H22 H 0.7512 0.6862 0.7925 0.021 Uiso 1 1 calc R . .
C23 C 0.75504(19) 0.79587(12) 0.85625(11) 0.0223(3) Uani 1 1 d . . .
H23 H 0.7921 0.7743 0.9129 0.027 Uiso 1 1 calc R . .
C24 C 0.72736(19) 0.87968(12) 0.84522(11) 0.0229(4) Uani 1 1 d . . .
H24 H 0.7476 0.9155 0.8941 0.028 Uiso 1 1 calc R . .
C25 C 0.67004(18) 0.91135(11) 0.76282(11) 0.0202(3) Uani 1 1 d . . .
H25 H 0.6520 0.9689 0.7553 0.024 Uiso 1 1 calc R . .
C26 C 0.63910(17) 0.85857(10) 0.69122(10) 0.0164(3) Uani 1 1 d . . .
H26 H 0.5971 0.8799 0.6351 0.020 Uiso 1 1 calc R . .
C31 C 0.72836(17) 0.75693(10) 0.33082(10) 0.0136(3) Uani 1 1 d . . .
C32 C 0.84186(18) 0.70136(10) 0.33726(11) 0.0196(3) Uani 1 1 d . . .
H32 H 0.9323 0.7128 0.3749 0.023 Uiso 1 1 calc R . .
C33 C 0.8216(2) 0.62927(11) 0.28827(13) 0.0239(4) Uani 1 1 d . . .
H33 H 0.8987 0.5916 0.2919 0.029 Uiso 1 1 calc R . .
C34 C 0.6884(2) 0.61205(11) 0.23382(12) 0.0244(4) Uani 1 1 d . . .
H34 H 0.6750 0.5628 0.2002 0.029 Uiso 1 1 calc R . .
C35 C 0.5761(2) 0.66631(11) 0.22870(11) 0.0236(4) Uani 1 1 d . . .
H35 H 0.4849 0.6537 0.1925 0.028 Uiso 1 1 calc R . .
C36 C 0.59554(18) 0.73956(11) 0.27636(10) 0.0179(3) Uani 1 1 d . . .
H36 H 0.5185 0.7774 0.2717 0.021 Uiso 1 1 calc R . .
C41 C 0.92909(16) 0.88649(9) 0.40262(10) 0.0133(3) Uani 1 1 d . . .
C42 C 1.03503(18) 0.88955(11) 0.47954(11) 0.0202(3) Uani 1 1 d . . .
H42 H 1.0157 0.8691 0.5320 0.024 Uiso 1 1 calc R . .
C43 C 1.16906(18) 0.92253(11) 0.47980(12) 0.0220(3) Uani 1 1 d . . .
H43 H 1.2411 0.9243 0.5323 0.026 Uiso 1 1 calc R . .
C44 C 1.19749(18) 0.95273(10) 0.40353(12) 0.0206(3) Uani 1 1 d . . .
H44 H 1.2888 0.9757 0.4040 0.025 Uiso 1 1 calc R . .
C45 C 1.09279(18) 0.94953(11) 0.32634(12) 0.0205(3) Uani 1 1 d . . .
H45 H 1.1125 0.9703 0.2741 0.025 Uiso 1 1 calc R . .
C46 C 0.95907(17) 0.91588(10) 0.32570(10) 0.0165(3) Uani 1 1 d . . .
H46 H 0.8880 0.9129 0.2728 0.020 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
P1 C21 1.8151(15) . ?
P1 C11 1.8190(16) . ?
P1 C1 1.8263(15) . ?
P1 Se1 2.1047(4) . ?
P2 C41 1.8109(16) . ?
P2 C31 1.8123(16) . ?
P2 C2 1.8207(15) . ?
P2 Se2 2.1082(4) . ?
C1 C2 1.531(2) . ?
C11 C12 1.397(2) . ?
C11 C16 1.398(2) . ?
C12 C13 1.393(2) . ?
C13 C14 1.386(3) . ?
C14 C15 1.389(3) . ?
C15 C16 1.391(2) . ?
C21 C26 1.396(2) . ?
C21 C22 1.399(2) . ?
C22 C23 1.389(2) . ?
C23 C24 1.386(3) . ?
C24 C25 1.389(3) . ?
C25 C26 1.394(2) . ?
C31 C36 1.391(2) . ?
C31 C32 1.398(2) . ?
C32 C33 1.389(2) . ?
C33 C34 1.393(3) . ?
C34 C35 1.378(3) . ?
C35 C36 1.394(2) . ?
C41 C42 1.393(2) . ?
C41 C46 1.396(2) . ?
C42 C43 1.391(2) . ?
C43 C44 1.385(2) . ?
C44 C45 1.390(3) . ?
C45 C46 1.392(2) . ?

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 P1 C11 107.22(7) . . ?
C21 P1 C1 106.52(7) . . ?
C11 P1 C1 104.36(7) . . ?
C21 P1 Se1 112.55(5) . . ?
C11 P1 Se1 114.16(6) . . ?
C1 P1 Se1 111.42(5) . . ?
C41 P2 C31 106.13(7) . . ?
C41 P2 C2 105.11(7) . . ?
C31 P2 C2 103.57(7) . . ?
C41 P2 Se2 114.50(5) . . ?
C31 P2 Se2 113.32(5) . . ?
C2 P2 Se2 113.23(6) . . ?
C2 C1 P1 111.39(10) . . ?
C1 C2 P2 111.77(10) . . ?
C12 C11 C16 119.84(15) . . ?
C12 C11 P1 119.68(13) . . ?
C16 C11 P1 120.47(12) . . ?
C13 C12 C11 120.07(16) . . ?
C14 C13 C12 119.81(17) . . ?
C13 C14 C15 120.40(17) . . ?
C14 C15 C16 120.21(17) . . ?
C15 C16 C11 119.67(16) . . ?
C26 C21 C22 119.46(14) . . ?
C26 C21 P1 122.56(12) . . ?
C22 C21 P1 117.97(12) . . ?
C23 C22 C21 119.95(16) . . ?
C24 C23 C22 120.32(16) . . ?
C23 C24 C25 120.14(16) . . ?
C24 C25 C26 119.87(16) . . ?
C25 C26 C21 120.21(15) . . ?
C36 C31 C32 120.08(15) . . ?
C36 C31 P2 119.68(12) . . ?
C32 C31 P2 120.11(12) . . ?
C33 C32 C31 119.61(16) . . ?
C32 C33 C34 120.16(17) . . ?
C35 C34 C33 120.09(16) . . ?
C34 C35 C36 120.37(16) . . ?
C31 C36 C35 119.67(16) . . ?
C42 C41 C46 119.46(15) . . ?
C42 C41 P2 122.44(12) . . ?
C46 C41 P2 118.08(12) . . ?
C43 C42 C41 120.22(15) . . ?
C44 C43 C42 120.07(16) . . ?
C43 C44 C45 120.16(15) . . ?
C44 C45 C46 119.91(15) . . ?
C45 C46 C41 120.17(15) . . ?

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
C21 P1 C1 C2 68.56(12) . . . . ?
C11 P1 C1 C2 -178.20(11) . . . . ?
Se1 P1 C1 C2 -54.54(12) . . . . ?
P1 C1 C2 P2 165.52(8) . . . . ?
C41 P2 C2 C1 -174.77(11) . . . . ?
C31 P2 C2 C1 -63.60(13) . . . . ?
Se2 P2 C2 C1 59.54(12) . . . . ?
C21 P1 C11 C12 -136.53(13) . . . . ?
C1 P1 C11 C12 110.73(13) . . . . ?
Se1 P1 C11 C12 -11.15(14) . . . . ?
C21 P1 C11 C16 44.62(14) . . . . ?
C1 P1 C11 C16 -68.13(14) . . . . ?
Se1 P1 C11 C16 170.00(11) . . . . ?
C16 C11 C12 C13 0.2(2) . . . . ?
P1 C11 C12 C13 -178.67(12) . . . . ?
C11 C12 C13 C14 0.2(3) . . . . ?
C12 C13 C14 C15 0.0(3) . . . . ?
C13 C14 C15 C16 -0.7(3) . . . . ?
C14 C15 C16 C11 1.1(3) . . . . ?
C12 C11 C16 C15 -0.9(2) . . . . ?
P1 C11 C16 C15 177.98(13) . . . . ?
C11 P1 C21 C26 -95.18(14) . . . . ?
C1 P1 C21 C26 16.09(15) . . . . ?
Se1 P1 C21 C26 138.48(12) . . . . ?
C11 P1 C21 C22 86.23(13) . . . . ?
C1 P1 C21 C22 -162.50(12) . . . . ?
Se1 P1 C21 C22 -40.12(13) . . . . ?
C26 C21 C22 C23 0.9(2) . . . . ?
P1 C21 C22 C23 179.51(13) . . . . ?
C21 C22 C23 C24 -2.3(3) . . . . ?
C22 C23 C24 C25 1.5(3) . . . . ?
C23 C24 C25 C26 0.6(3) . . . . ?
C24 C25 C26 C21 -2.0(2) . . . . ?
C22 C21 C26 C25 1.2(2) . . . . ?
P1 C21 C26 C25 -177.34(12) . . . . ?
C41 P2 C31 C36 -144.27(13) . . . . ?
C2 P2 C31 C36 105.30(13) . . . . ?
Se2 P2 C31 C36 -17.78(14) . . . . ?
C41 P2 C31 C32 39.80(15) . . . . ?
C2 P2 C31 C32 -70.63(14) . . . . ?
Se2 P2 C31 C32 166.29(11) . . . . ?
C36 C31 C32 C33 0.7(2) . . . . ?
P2 C31 C32 C33 176.62(13) . . . . ?
C31 C32 C33 C34 -0.7(3) . . . . ?
C32 C33 C34 C35 -0.3(3) . . . . ?
C33 C34 C35 C36 1.4(3) . . . . ?
C32 C31 C36 C35 0.4(2) . . . . ?
P2 C31 C36 C35 -175.56(13) . . . . ?
C34 C35 C36 C31 -1.4(3) . . . . ?
C31 P2 C41 C42 -116.15(14) . . . . ?
C2 P2 C41 C42 -6.82(16) . . . . ?
Se2 P2 C41 C42 118.08(13) . . . . ?
C31 P2 C41 C46 65.75(14) . . . . ?
C2 P2 C41 C46 175.08(12) . . . . ?
Se2 P2 C41 C46 -60.03(13) . . . . ?
C46 C41 C42 C43 0.7(3) . . . . ?
P2 C41 C42 C43 -177.34(13) . . . . ?
C41 C42 C43 C44 0.2(3) . . . . ?
C42 C43 C44 C45 -0.6(3) . . . . ?
C43 C44 C45 C46 0.0(3) . . . . ?
C44 C45 C46 C41 1.0(2) . . . . ?
C42 C41 C46 C45 -1.3(2) . . . . ?
P2 C41 C46 C45 176.82(13) . . . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        30.03
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.725
_refine_diff_density_min         -0.356
_refine_diff_density_rms         0.072


# end of cif file
####################################################################### 
# 
# 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_martin
_database_code_depnum_ccdc_archive 'CCDC 1579324'
_audit_update_record             
;
2017-10-11 deposited with the CCDC.
2018-02-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C27 H26 Cl2 P2 Se2'
_chemical_formula_weight         641.24

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'
P P 0.1023 0.0942 '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'
Se Se -0.0929 2.2259 '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/n'

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

_cell_length_a                   12.1314(4)
_cell_length_b                   16.1003(4)
_cell_length_c                   14.9640(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 111.591(4)
_cell_angle_gamma                90.00
_cell_volume                     2717.67(14)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    18241
_cell_measurement_theta_min      2.2001
_cell_measurement_theta_max      30.8029

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.02
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.567
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1280
_exptl_absorpt_coefficient_mu    3.050
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.52415
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
; 
CrysAlisPro, Oxford Diffraction Ltd., 
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) 
(compiled Jan 23 2012,18:06:46) 
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur, Eos'
_diffrn_measurement_method       ω-scan
_diffrn_detector_area_resol_mean 16.1419
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            105404
_diffrn_reflns_av_R_equivalents  0.0503
_diffrn_reflns_av_sigmaI/netI    0.0227
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.20
_diffrn_reflns_theta_max         29.13
_reflns_number_total             7312
_reflns_number_gt                6121
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
; 
CrysAlisPro, Oxford Diffraction Ltd., 
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) 
(compiled Jan 23 2012,18:06:46) 
;
_computing_cell_refinement       
; 
CrysAlisPro, Oxford Diffraction Ltd., 
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) 
(compiled Jan 23 2012,18:06:46) 
;
_computing_data_reduction        
; 
CrysAlisPro, Oxford Diffraction Ltd., 
Version 1.171.35.21 (release 20-01-2012 CrysAlis171 .NET) 
(compiled Jan 23 2012,18:06:46) 
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker XP'
_computing_publication_material  SHELXL-97

_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. 

 The dichloromethane molecule is slightly disordered, the second component
 being 10% occupied. Appropriate restraints were employed to improve the
 refinement stability, but the dimensions of disordered groups should
 always be interpreted with caution.
;

_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)+(0.0346P)²+3.4827P] 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_number_reflns         7312
_refine_ls_number_parameters     311
_refine_ls_number_restraints     19
_refine_ls_R_factor_all          0.0441
_refine_ls_R_factor_gt           0.0332
_refine_ls_wR_factor_ref         0.0800
_refine_ls_wR_factor_gt          0.0758
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_restrained_S_all      1.040
_refine_ls_shift/su_max          0.010
_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
P1 P 0.17970(5) 0.44651(3) 0.57872(4) 0.01615(11) Uani 1 1 d . . .
P2 P 0.86528(5) 0.53629(3) 0.85883(4) 0.01364(11) Uani 1 1 d . . .
Se1 Se 0.14987(2) 0.380009(16) 0.689892(19) 0.02734(7) Uani 1 1 d . . .
Se2 Se 0.75451(2) 0.611854(14) 0.905230(17) 0.02078(6) Uani 1 1 d . . .
C1 C 0.04233(18) 0.47549(14) 0.48212(17) 0.0208(5) Uani 1 1 d . . .
H1A H 0.0613 0.5096 0.4346 0.025 Uiso 1 1 calc R . .
H1B H 0.0018 0.4245 0.4491 0.025 Uiso 1 1 calc R . .
C2 C 0.9628(2) 0.47350(13) 0.95707(15) 0.0215(5) Uani 1 1 d . . .
H2A H 0.9145 0.4340 0.9780 0.026 Uiso 1 1 calc R . .
H2B H 1.0162 0.4408 0.9341 0.026 Uiso 1 1 calc R . .
C11 C 0.26272(18) 0.38748(13) 0.52122(15) 0.0167(4) Uani 1 1 d . . .
C12 C 0.2721(2) 0.30187(15) 0.53291(19) 0.0249(5) Uani 1 1 d . . .
H12 H 0.2350 0.2746 0.5707 0.030 Uiso 1 1 calc R . .
C13 C 0.3354(3) 0.25620(16) 0.4896(2) 0.0332(6) Uani 1 1 d . . .
H13 H 0.3412 0.1976 0.4976 0.040 Uiso 1 1 calc R . .
C14 C 0.3902(2) 0.29506(16) 0.43478(18) 0.0268(5) Uani 1 1 d . . .
H14 H 0.4333 0.2633 0.4051 0.032 Uiso 1 1 calc R . .
C15 C 0.3821(2) 0.38072(15) 0.42312(17) 0.0245(5) Uani 1 1 d . . .
H15 H 0.4202 0.4076 0.3859 0.029 Uiso 1 1 calc R . .
C16 C 0.3183(2) 0.42717(14) 0.46580(16) 0.0199(4) Uani 1 1 d . . .
H16 H 0.3123 0.4857 0.4574 0.024 Uiso 1 1 calc R . .
C21 C 0.26405(18) 0.54108(14) 0.61989(15) 0.0168(4) Uani 1 1 d . . .
C22 C 0.3618(2) 0.53802(16) 0.70665(17) 0.0235(5) Uani 1 1 d . . .
H22 H 0.3816 0.4876 0.7419 0.028 Uiso 1 1 calc R . .
C23 C 0.4295(2) 0.60848(18) 0.74093(19) 0.0307(6) Uani 1 1 d . . .
H23 H 0.4958 0.6062 0.7998 0.037 Uiso 1 1 calc R . .
C24 C 0.4013(2) 0.68212(17) 0.6900(2) 0.0310(6) Uani 1 1 d . . .
H24 H 0.4477 0.7304 0.7144 0.037 Uiso 1 1 calc R . .
C25 C 0.3058(2) 0.68584(16) 0.6038(2) 0.0281(5) Uani 1 1 d . . .
H25 H 0.2873 0.7364 0.5686 0.034 Uiso 1 1 calc R . .
C26 C 0.2364(2) 0.61516(14) 0.56849(17) 0.0218(4) Uani 1 1 d . . .
H26 H 0.1705 0.6177 0.5094 0.026 Uiso 1 1 calc R . .
C31 C 0.96012(19) 0.59431(13) 0.81230(15) 0.0165(4) Uani 1 1 d . . .
C32 C 0.9131(2) 0.66413(14) 0.75572(16) 0.0221(5) Uani 1 1 d . . .
H32 H 0.8331 0.6799 0.7423 0.026 Uiso 1 1 calc R . .
C33 C 0.9836(3) 0.71058(17) 0.71901(19) 0.0343(6) Uani 1 1 d . . .
H33 H 0.9512 0.7574 0.6794 0.041 Uiso 1 1 calc R . .
C34 C 1.1004(3) 0.68865(19) 0.7401(2) 0.0408(8) Uani 1 1 d . . .
H34 H 1.1487 0.7213 0.7161 0.049 Uiso 1 1 calc R . .
C35 C 1.1475(3) 0.61967(19) 0.7957(2) 0.0387(7) Uani 1 1 d . . .
H35 H 1.2279 0.6049 0.8096 0.046 Uiso 1 1 calc R . .
C36 C 1.0777(2) 0.57179(16) 0.83141(19) 0.0269(5) Uani 1 1 d . . .
H36 H 1.1100 0.5238 0.8688 0.032 Uiso 1 1 calc R . .
C41 C 0.78873(18) 0.45912(12) 0.76975(14) 0.0143(4) Uani 1 1 d . . .
C42 C 0.8545(2) 0.40646(14) 0.73379(16) 0.0182(4) Uani 1 1 d . . .
H42 H 0.9377 0.4138 0.7530 0.022 Uiso 1 1 calc R . .
C43 C 0.7978(2) 0.34343(14) 0.66991(16) 0.0209(4) Uani 1 1 d . . .
H43 H 0.8425 0.3071 0.6463 0.025 Uiso 1 1 calc R . .
C44 C 0.6753(2) 0.33356(14) 0.64043(16) 0.0223(5) Uani 1 1 d . . .
H44 H 0.6367 0.2906 0.5966 0.027 Uiso 1 1 calc R . .
C45 C 0.6097(2) 0.38647(14) 0.67495(17) 0.0215(4) Uani 1 1 d . . .
H45 H 0.5262 0.3800 0.6542 0.026 Uiso 1 1 calc R . .
C46 C 0.66638(19) 0.44899(13) 0.74008(15) 0.0175(4) Uani 1 1 d . . .
H46 H 0.6216 0.4847 0.7643 0.021 Uiso 1 1 calc R . .
C99 C 0.9360(3) 0.1269(2) 0.4476(2) 0.0349(7) Uani 0.9071(18) 1 d PDU A 1
H99A H 0.8948 0.0876 0.4757 0.042 Uiso 0.9071(18) 1 calc PR A 1
H99B H 0.8792 0.1445 0.3839 0.042 Uiso 0.9071(18) 1 calc PR A 1
Cl1 Cl 1.05915(9) 0.07690(5) 0.43403(7) 0.0397(2) Uani 0.9071(18) 1 d PDU A 1
Cl2 Cl 0.98450(6) 0.21588(4) 0.52448(5) 0.02871(18) Uani 0.9071(18) 1 d PD A 1
C99' C 0.9800(10) 0.1183(12) 0.4975(11) 0.005(3) Uiso 0.0929(18) 1 d PDU A 2
H99C H 0.9957 0.1759 0.5219 0.006 Uiso 0.0929(18) 1 calc PR A 2
H99D H 0.9608 0.0847 0.5453 0.006 Uiso 0.0929(18) 1 calc PR A 2
Cl1' Cl 0.8551(4) 0.1176(3) 0.3847(3) 0.0078(12) Uiso 0.0929(18) 1 d PD A 2
Cl2' Cl 1.1095(6) 0.0771(4) 0.4836(5) 0.0196(14) Uiso 0.0929(18) 1 d PDU A 2


_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
P1 C21 1.811(2) . ?
P1 C11 1.815(2) . ?
P1 C1 1.820(2) . ?
P1 Se1 2.1185(6) . ?
P2 C31 1.809(2) . ?
P2 C41 1.809(2) . ?
P2 C2 1.817(2) . ?
P2 Se2 2.1106(6) . ?
C1 C1 1.539(4) 3_566 ?
C2 C2 1.530(4) 3_767 ?
C11 C12 1.389(3) . ?
C11 C16 1.400(3) . ?
C12 C13 1.385(3) . ?
C13 C14 1.381(4) . ?
C14 C15 1.389(3) . ?
C15 C16 1.389(3) . ?
C21 C26 1.392(3) . ?
C21 C22 1.401(3) . ?
C22 C23 1.384(4) . ?
C23 C24 1.382(4) . ?
C24 C25 1.382(4) . ?
C25 C26 1.398(3) . ?
C31 C36 1.396(3) . ?
C31 C32 1.397(3) . ?
C32 C33 1.392(3) . ?
C33 C34 1.380(4) . ?
C34 C35 1.379(5) . ?
C35 C36 1.389(4) . ?
C41 C46 1.393(3) . ?
C41 C42 1.400(3) . ?
C42 C43 1.390(3) . ?
C43 C44 1.394(3) . ?
C44 C45 1.388(3) . ?
C45 C46 1.394(3) . ?
C99 Cl1 1.774(3) . ?
C99 Cl2 1.795(3) . ?
C99' Cl2' 1.786(12) . ?
C99' Cl1' 1.806(13) . ?

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 P1 C11 104.99(10) . . ?
C21 P1 C1 107.00(10) . . ?
C11 P1 C1 105.27(10) . . ?
C21 P1 Se1 113.33(7) . . ?
C11 P1 Se1 113.11(7) . . ?
C1 P1 Se1 112.47(8) . . ?
C31 P2 C41 107.34(10) . . ?
C31 P2 C2 106.37(11) . . ?
C41 P2 C2 102.64(9) . . ?
C31 P2 Se2 113.65(7) . . ?
C41 P2 Se2 114.96(7) . . ?
C2 P2 Se2 110.99(8) . . ?
C1 C1 P1 112.9(2) 3_566 . ?
C2 C2 P2 112.1(2) 3_767 . ?
C12 C11 C16 119.5(2) . . ?
C12 C11 P1 119.59(17) . . ?
C16 C11 P1 120.90(17) . . ?
C13 C12 C11 120.1(2) . . ?
C14 C13 C12 120.6(2) . . ?
C13 C14 C15 119.8(2) . . ?
C14 C15 C16 120.2(2) . . ?
C15 C16 C11 119.8(2) . . ?
C26 C21 C22 119.5(2) . . ?
C26 C21 P1 122.78(17) . . ?
C22 C21 P1 117.74(18) . . ?
C23 C22 C21 120.0(2) . . ?
C24 C23 C22 120.4(2) . . ?
C25 C24 C23 120.3(2) . . ?
C24 C25 C26 119.9(2) . . ?
C21 C26 C25 120.0(2) . . ?
C36 C31 C32 119.5(2) . . ?
C36 C31 P2 122.28(19) . . ?
C32 C31 P2 118.23(17) . . ?
C33 C32 C31 119.9(2) . . ?
C34 C33 C32 120.0(3) . . ?
C35 C34 C33 120.5(2) . . ?
C34 C35 C36 120.2(3) . . ?
C35 C36 C31 119.9(3) . . ?
C46 C41 C42 119.83(19) . . ?
C46 C41 P2 120.86(16) . . ?
C42 C41 P2 119.24(16) . . ?
C43 C42 C41 119.9(2) . . ?
C42 C43 C44 120.0(2) . . ?
C45 C44 C43 120.1(2) . . ?
C44 C45 C46 120.0(2) . . ?
C41 C46 C45 120.0(2) . . ?
Cl1 C99 Cl2 110.12(18) . . ?
Cl2' C99' Cl1' 111.1(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
C21 P1 C1 C1 -70.3(3) . . . 3_566 ?
C11 P1 C1 C1 178.4(2) . . . 3_566 ?
Se1 P1 C1 C1 54.8(2) . . . 3_566 ?
C31 P2 C2 C2 68.0(3) . . . 3_767 ?
C41 P2 C2 C2 -179.5(2) . . . 3_767 ?
Se2 P2 C2 C2 -56.1(3) . . . 3_767 ?
C21 P1 C11 C12 141.12(19) . . . . ?
C1 P1 C11 C12 -106.1(2) . . . . ?
Se1 P1 C11 C12 17.1(2) . . . . ?
C21 P1 C11 C16 -38.4(2) . . . . ?
C1 P1 C11 C16 74.4(2) . . . . ?
Se1 P1 C11 C16 -162.46(16) . . . . ?
C16 C11 C12 C13 -0.3(4) . . . . ?
P1 C11 C12 C13 -179.9(2) . . . . ?
C11 C12 C13 C14 0.3(4) . . . . ?
C12 C13 C14 C15 0.1(4) . . . . ?
C13 C14 C15 C16 -0.5(4) . . . . ?
C14 C15 C16 C11 0.4(4) . . . . ?
C12 C11 C16 C15 0.0(3) . . . . ?
P1 C11 C16 C15 179.50(18) . . . . ?
C11 P1 C21 C26 97.7(2) . . . . ?
C1 P1 C21 C26 -13.8(2) . . . . ?
Se1 P1 C21 C26 -138.34(17) . . . . ?
C11 P1 C21 C22 -81.40(18) . . . . ?
C1 P1 C21 C22 167.07(17) . . . . ?
Se1 P1 C21 C22 42.52(19) . . . . ?
C26 C21 C22 C23 0.5(3) . . . . ?
P1 C21 C22 C23 179.65(18) . . . . ?
C21 C22 C23 C24 0.0(4) . . . . ?
C22 C23 C24 C25 -0.7(4) . . . . ?
C23 C24 C25 C26 0.9(4) . . . . ?
C22 C21 C26 C25 -0.3(3) . . . . ?
P1 C21 C26 C25 -179.42(18) . . . . ?
C24 C25 C26 C21 -0.4(4) . . . . ?
C41 P2 C31 C36 -91.6(2) . . . . ?
C2 P2 C31 C36 17.7(2) . . . . ?
Se2 P2 C31 C36 140.15(17) . . . . ?
C41 P2 C31 C32 88.68(18) . . . . ?
C2 P2 C31 C32 -162.01(17) . . . . ?
Se2 P2 C31 C32 -39.59(19) . . . . ?
C36 C31 C32 C33 -0.1(3) . . . . ?
P2 C31 C32 C33 179.70(18) . . . . ?
C31 C32 C33 C34 -1.3(4) . . . . ?
C32 C33 C34 C35 1.5(4) . . . . ?
C33 C34 C35 C36 -0.3(4) . . . . ?
C34 C35 C36 C31 -1.0(4) . . . . ?
C32 C31 C36 C35 1.2(3) . . . . ?
P2 C31 C36 C35 -178.53(19) . . . . ?
C31 P2 C41 C46 -131.12(18) . . . . ?
C2 P2 C41 C46 117.00(18) . . . . ?
Se2 P2 C41 C46 -3.62(19) . . . . ?
C31 P2 C41 C42 51.91(19) . . . . ?
C2 P2 C41 C42 -59.97(19) . . . . ?
Se2 P2 C41 C42 179.41(14) . . . . ?
C46 C41 C42 C43 -1.1(3) . . . . ?
P2 C41 C42 C43 175.92(17) . . . . ?
C41 C42 C43 C44 1.1(3) . . . . ?
C42 C43 C44 C45 -0.2(3) . . . . ?
C43 C44 C45 C46 -0.8(3) . . . . ?
C42 C41 C46 C45 0.1(3) . . . . ?
P2 C41 C46 C45 -176.81(17) . . . . ?
C44 C45 C46 C41 0.8(3) . . . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        29.13
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         1.081
_refine_diff_density_min         -0.777
_refine_diff_density_rms         0.082


# end of cif file
####################################################################### 
# 
# 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_john
_database_code_depnum_ccdc_archive 'CCDC 1494788'
_audit_update_record             
;
2016-07-19 deposited with the CCDC.
2018-02-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H24 Br4 P2 S'
_chemical_formula_weight         750.09

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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C c'

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

_cell_length_a                   15.8873(3)
_cell_length_b                   9.6949(2)
_cell_length_c                   18.3533(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 101.565(3)
_cell_angle_gamma                90.00
_cell_volume                     2769.48(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    16555
_cell_measurement_theta_min      2.4730
_cell_measurement_theta_max      30.5680

_exptl_crystal_description       'irregular  plate'
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.799
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1464
_exptl_absorpt_coefficient_mu    6.018
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.40274
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) 
(compiled Aug 13 2014,18:06:01) 
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur, Eos'
_diffrn_measurement_method       'ω scan'
_diffrn_detector_area_resol_mean 16.1419
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            71971
_diffrn_reflns_av_R_equivalents  0.0475
_diffrn_reflns_av_sigmaI/netI    0.0348
_diffrn_reflns_limit_h_min       -22
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.27
_diffrn_reflns_theta_max         31.05
_reflns_number_total             8177
_reflns_number_gt                7400
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) 
(compiled Aug 13 2014,18:06:01) 
;
_computing_cell_refinement       
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) 
(compiled Aug 13 2014,18:06:01) 
;
_computing_data_reduction        
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) 
(compiled Aug 13 2014,18:06:01) 
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker XP'
_computing_publication_material  SHELXL-97

_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. 
  
 The structure was refined as an enantiomeric twin. 
;

_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)+(0.0220P)²+0.9957P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.118(4)
_refine_ls_number_reflns         8177
_refine_ls_number_parameters     299
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.0354
_refine_ls_R_factor_gt           0.0279
_refine_ls_wR_factor_ref         0.0539
_refine_ls_wR_factor_gt          0.0519
_refine_ls_goodness_of_fit_ref   1.055
_refine_ls_restrained_S_all      1.055
_refine_ls_shift/su_max          0.002
_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
P1 P 0.25196(4) 0.43028(6) 0.40403(4) 0.01068(13) Uani 1 1 d . . .
P2 P 0.38331(4) 0.09846(6) 0.54624(4) 0.01155(13) Uani 1 1 d . . .
S1 S 0.32219(4) 0.58529(6) 0.44861(4) 0.01451(13) Uani 1 1 d . . .
Br1 Br 0.31005(2) -0.07320(2) 0.492382(18) 0.01564(6) Uani 1 1 d . . .
Br2 Br 0.098998(19) -0.00827(3) 0.341158(18) 0.02461(8) Uani 1 1 d . . .
Br3 Br 0.06729(2) -0.00964(3) 0.47243(2) 0.01854(5) Uani 1 1 d . . .
Br4 Br 0.035949(18) -0.00903(3) 0.602943(17) 0.02449(8) Uani 1 1 d . . .
C01 C 0.26844(17) 0.2769(3) 0.46298(15) 0.0132(5) Uani 1 1 d . . .
H01A H 0.2458 0.2935 0.5087 0.016 Uiso 1 1 calc R . .
H01B H 0.2368 0.1980 0.4362 0.016 Uiso 1 1 calc R . .
C02 C 0.36478(17) 0.2424(3) 0.48387(15) 0.0126(5) Uani 1 1 d . . .
H02A H 0.3967 0.3236 0.5077 0.015 Uiso 1 1 calc R . .
H02B H 0.3864 0.2205 0.4382 0.015 Uiso 1 1 calc R . .
C11 C 0.27648(17) 0.3718(2) 0.31696(15) 0.0122(5) Uani 1 1 d . . .
C12 C 0.35455(18) 0.4064(3) 0.29886(16) 0.0155(6) Uani 1 1 d . . .
H12 H 0.3950 0.4602 0.3323 0.019 Uiso 1 1 calc R . .
C13 C 0.37366(19) 0.3624(3) 0.23183(17) 0.0209(6) Uani 1 1 d . . .
H13 H 0.4262 0.3887 0.2187 0.025 Uiso 1 1 calc R . .
C14 C 0.3161(2) 0.2807(3) 0.18471(17) 0.0225(7) Uani 1 1 d . . .
H14 H 0.3294 0.2503 0.1391 0.027 Uiso 1 1 calc R . .
C15 C 0.2386(2) 0.2422(3) 0.20333(17) 0.0224(6) Uani 1 1 d . . .
H15 H 0.1995 0.1845 0.1709 0.027 Uiso 1 1 calc R . .
C16 C 0.21881(19) 0.2881(3) 0.26892(16) 0.0170(6) Uani 1 1 d . . .
H16 H 0.1658 0.2627 0.2815 0.020 Uiso 1 1 calc R . .
C21 C 0.13776(16) 0.4619(3) 0.38591(15) 0.0131(5) Uani 1 1 d . . .
C22 C 0.10820(17) 0.5876(3) 0.35431(15) 0.0181(6) Uani 1 1 d . . .
H22 H 0.1479 0.6549 0.3444 0.022 Uiso 1 1 calc R . .
C23 C 0.02109(17) 0.6149(3) 0.33736(16) 0.0215(6) Uani 1 1 d . . .
H23 H 0.0011 0.7004 0.3151 0.026 Uiso 1 1 calc R . .
C24 C -0.03713(19) 0.5188(3) 0.35257(18) 0.0222(7) Uani 1 1 d . . .
H24 H -0.0970 0.5374 0.3397 0.027 Uiso 1 1 calc R . .
C25 C -0.00843(18) 0.3952(3) 0.38656(17) 0.0188(6) Uani 1 1 d . . .
H25 H -0.0484 0.3307 0.3989 0.023 Uiso 1 1 calc R . .
C26 C 0.07910(19) 0.3655(3) 0.40269(16) 0.0152(5) Uani 1 1 d . . .
H26 H 0.0989 0.2800 0.4250 0.018 Uiso 1 1 calc R . .
C31 C 0.34744(18) 0.1389(2) 0.62958(15) 0.0127(5) Uani 1 1 d . . .
C32 C 0.26862(18) 0.0950(3) 0.64404(16) 0.0144(5) Uani 1 1 d . . .
H32 H 0.2311 0.0395 0.6091 0.017 Uiso 1 1 calc R . .
C33 C 0.24627(19) 0.1338(3) 0.71017(16) 0.0193(6) Uani 1 1 d . . .
H33 H 0.1933 0.1036 0.7212 0.023 Uiso 1 1 calc R . .
C34 C 0.3005(2) 0.2163(3) 0.76020(17) 0.0226(6) Uani 1 1 d . . .
H34 H 0.2848 0.2415 0.8057 0.027 Uiso 1 1 calc R . .
C35 C 0.3774(2) 0.2626(3) 0.74464(17) 0.0221(6) Uani 1 1 d . . .
H35 H 0.4134 0.3215 0.7788 0.027 Uiso 1 1 calc R . .
C36 C 0.40193(18) 0.2235(3) 0.67993(16) 0.0178(6) Uani 1 1 d . . .
H36 H 0.4552 0.2536 0.6696 0.021 Uiso 1 1 calc R . .
C41 C 0.49309(17) 0.0491(3) 0.56899(16) 0.0159(5) Uani 1 1 d . . .
C42 C 0.55611(19) 0.1165(3) 0.53963(17) 0.0161(5) Uani 1 1 d . . .
H42 H 0.5416 0.1908 0.5057 0.019 Uiso 1 1 calc R . .
C43 C 0.64058(18) 0.0728(3) 0.56101(17) 0.0206(6) Uani 1 1 d . . .
H43 H 0.6844 0.1180 0.5416 0.025 Uiso 1 1 calc R . .
C44 C 0.66173(19) -0.0350(3) 0.60987(18) 0.0265(7) Uani 1 1 d . . .
H44 H 0.7200 -0.0632 0.6241 0.032 Uiso 1 1 calc R . .
C45 C 0.59911(19) -0.1027(3) 0.6386(2) 0.0335(8) Uani 1 1 d . . .
H45 H 0.6141 -0.1778 0.6719 0.040 Uiso 1 1 calc R . .
C46 C 0.51447(19) -0.0606(3) 0.6185(2) 0.0306(8) Uani 1 1 d . . .
H46 H 0.4711 -0.1062 0.6383 0.037 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. 

 Short contacts:

      3.4215 (0.0006)  S1 - Br1_$1
      3.9511 (0.0005)  Br1 - Br2
      3.8501 (0.0005)  Br1 - Br3

 Operator for generating equivalent atoms:
 $1   x, y+1, z

;

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
P1 C21 1.804(3) . ?
P1 C11 1.810(3) . ?
P1 C01 1.827(3) . ?
P1 S1 1.9511(9) . ?
P2 C41 1.776(3) . ?
P2 C31 1.780(3) . ?
P2 C02 1.791(3) . ?
P2 Br1 2.1540(7) . ?
Br2 Br3 2.5583(5) . ?
Br3 Br4 2.5424(5) . ?
C01 C02 1.538(3) . ?
C11 C12 1.388(4) . ?
C11 C16 1.397(4) . ?
C12 C13 1.392(4) . ?
C13 C14 1.376(4) . ?
C14 C15 1.394(4) . ?
C15 C16 1.377(4) . ?
C21 C22 1.391(4) . ?
C21 C26 1.397(4) . ?
C22 C23 1.382(4) . ?
C23 C24 1.381(4) . ?
C24 C25 1.385(4) . ?
C25 C26 1.392(4) . ?
C31 C32 1.397(4) . ?
C31 C36 1.398(4) . ?
C32 C33 1.383(4) . ?
C33 C34 1.381(4) . ?
C34 C35 1.385(4) . ?
C35 C36 1.375(4) . ?
C41 C42 1.392(4) . ?
C41 C46 1.396(4) . ?
C42 C43 1.387(4) . ?
C43 C44 1.374(4) . ?
C44 C45 1.381(4) . ?
C45 C46 1.383(4) . ?

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 P1 C11 106.07(12) . . ?
C21 P1 C01 105.48(13) . . ?
C11 P1 C01 103.73(12) . . ?
C21 P1 S1 114.58(9) . . ?
C11 P1 S1 113.90(9) . . ?
C01 P1 S1 112.13(9) . . ?
C41 P2 C31 109.02(13) . . ?
C41 P2 C02 112.84(13) . . ?
C31 P2 C02 109.74(12) . . ?
C41 P2 Br1 108.33(9) . . ?
C31 P2 Br1 109.14(9) . . ?
C02 P2 Br1 107.70(9) . . ?
Br4 Br3 Br2 179.568(16) . . ?
C02 C01 P1 110.01(16) . . ?
C01 C02 P2 110.90(15) . . ?
C12 C11 C16 119.6(3) . . ?
C12 C11 P1 119.8(2) . . ?
C16 C11 P1 120.6(2) . . ?
C11 C12 C13 120.1(3) . . ?
C14 C13 C12 119.8(3) . . ?
C13 C14 C15 120.6(3) . . ?
C16 C15 C14 119.7(3) . . ?
C15 C16 C11 120.2(3) . . ?
C22 C21 C26 119.6(2) . . ?
C22 C21 P1 118.0(2) . . ?
C26 C21 P1 122.4(2) . . ?
C23 C22 C21 120.1(3) . . ?
C24 C23 C22 120.4(3) . . ?
C23 C24 C25 120.1(3) . . ?
C24 C25 C26 119.9(3) . . ?
C25 C26 C21 119.8(2) . . ?
C32 C31 C36 120.9(3) . . ?
C32 C31 P2 123.3(2) . . ?
C36 C31 P2 115.8(2) . . ?
C33 C32 C31 118.7(3) . . ?
C34 C33 C32 120.4(3) . . ?
C33 C34 C35 120.6(3) . . ?
C36 C35 C34 120.2(3) . . ?
C35 C36 C31 119.2(3) . . ?
C42 C41 C46 120.7(3) . . ?
C42 C41 P2 122.1(2) . . ?
C46 C41 P2 117.3(2) . . ?
C43 C42 C41 118.5(3) . . ?
C44 C43 C42 120.9(3) . . ?
C43 C44 C45 120.7(3) . . ?
C44 C45 C46 119.6(3) . . ?
C45 C46 C41 119.7(3) . . ?

_diffrn_measured_fraction_theta_max 0.948
_diffrn_reflns_theta_full        30.00
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.642
_refine_diff_density_min         -0.496
_refine_diff_density_rms         0.087


# end of cif file
####################################################################### 
# 
# 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_samuel
_database_code_depnum_ccdc_archive 'CCDC 1579326'
_audit_update_record             
;
2017-10-11 deposited with the CCDC.
2018-02-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H32 P2 Se2'
_chemical_formula_weight         420.26

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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.0929 2.2259 '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/n'

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

_cell_length_a                   9.3133(5)
_cell_length_b                   10.4104(4)
_cell_length_c                   10.1508(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.577(4)
_cell_angle_gamma                90.00
_cell_volume                     952.49(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    5494
_cell_measurement_theta_min      2.6450
_cell_measurement_theta_max      30.0730

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.465
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             428
_exptl_absorpt_coefficient_mu    4.036
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.65025
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
; 
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015) 
Empirical absorption correction using spherical harmonics, 
 implemented in SCALE3 ABSPACK scaling algorithm. 
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur, Eos'
_diffrn_measurement_method       ω-scan
_diffrn_detector_area_resol_mean 16.1419
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            24692
_diffrn_reflns_av_R_equivalents  0.0423
_diffrn_reflns_av_sigmaI/netI    0.0257
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.65
_diffrn_reflns_theta_max         30.03
_reflns_number_total             2767
_reflns_number_gt                2285
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker XP'
_computing_publication_material  SHELXL-97

_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)+(0.0207P)²+0.7947P] 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_number_reflns         2767
_refine_ls_number_parameters     86
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0433
_refine_ls_R_factor_gt           0.0309
_refine_ls_wR_factor_ref         0.0643
_refine_ls_wR_factor_gt          0.0604
_refine_ls_goodness_of_fit_ref   1.068
_refine_ls_restrained_S_all      1.068
_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
Se1 Se 0.53957(3) 0.05522(2) 0.83243(2) 0.03267(8) Uani 1 1 d . . .
P1 P 0.50445(5) 0.16053(5) 0.64889(5) 0.01909(11) Uani 1 1 d . . .
C01 C 0.4499(2) 0.05772(19) 0.4993(2) 0.0271(4) Uani 1 1 d . . .
H01A H 0.3476 0.0267 0.4915 0.033 Uiso 1 1 calc R . .
H01B H 0.4485 0.1099 0.4174 0.033 Uiso 1 1 calc R . .
C1 C 0.6663(2) 0.2544(2) 0.6337(2) 0.0299(5) Uani 1 1 d . . .
H1 H 0.6788 0.3245 0.7031 0.036 Uiso 1 1 calc R . .
C2 C 0.3514(2) 0.27556(19) 0.6262(2) 0.0269(4) Uani 1 1 d . . .
H2 H 0.3392 0.3179 0.5356 0.032 Uiso 1 1 calc R . .
C11 C 0.6423(3) 0.3202(4) 0.4960(3) 0.0678(10) Uani 1 1 d . . .
H11A H 0.7297 0.3720 0.4943 0.102 Uiso 1 1 calc R . .
H11B H 0.5549 0.3759 0.4810 0.102 Uiso 1 1 calc R . .
H11C H 0.6269 0.2551 0.4241 0.102 Uiso 1 1 calc R . .
C12 C 0.8102(3) 0.1776(3) 0.6680(3) 0.0513(7) Uani 1 1 d . . .
H12A H 0.8134 0.1214 0.5913 0.077 Uiso 1 1 calc R . .
H12B H 0.8148 0.1253 0.7492 0.077 Uiso 1 1 calc R . .
H12C H 0.8949 0.2366 0.6854 0.077 Uiso 1 1 calc R . .
C21 C 0.3854(3) 0.3799(2) 0.7355(3) 0.0460(6) Uani 1 1 d . . .
H21A H 0.2994 0.4368 0.7246 0.069 Uiso 1 1 calc R . .
H21B H 0.4715 0.4299 0.7263 0.069 Uiso 1 1 calc R . .
H21C H 0.4072 0.3399 0.8258 0.069 Uiso 1 1 calc R . .
C22 C 0.2055(2) 0.2091(2) 0.6268(3) 0.0369(5) Uani 1 1 d . . .
H22A H 0.2169 0.1619 0.7124 0.055 Uiso 1 1 calc R . .
H22B H 0.1789 0.1490 0.5502 0.055 Uiso 1 1 calc R . .
H22C H 0.1271 0.2736 0.6184 0.055 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
Se1 P1 2.1150(5) . ?
P1 C01 1.8222(19) . ?
P1 C2 1.831(2) . ?
P1 C1 1.835(2) . ?
C01 C01 1.520(4) 3_656 ?
C1 C11 1.522(3) . ?
C1 C12 1.524(3) . ?
C2 C22 1.526(3) . ?
C2 C21 1.528(3) . ?

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
C01 P1 C2 103.55(9) . . ?
C01 P1 C1 107.80(10) . . ?
C2 P1 C1 105.72(10) . . ?
C01 P1 Se1 112.23(7) . . ?
C2 P1 Se1 113.12(7) . . ?
C1 P1 Se1 113.68(7) . . ?
C01 C01 P1 114.52(18) 3_656 . ?
C11 C1 C12 111.3(2) . . ?
C11 C1 P1 112.51(16) . . ?
C12 C1 P1 113.27(17) . . ?
C22 C2 C21 109.98(19) . . ?
C22 C2 P1 111.61(15) . . ?
C21 C2 P1 111.15(16) . . ?

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
C2 P1 C01 C01 -173.0(2) . . . 3_656 ?
C1 P1 C01 C01 75.2(2) . . . 3_656 ?
Se1 P1 C01 C01 -50.7(2) . . . 3_656 ?
C01 P1 C1 C11 50.2(2) . . . . ?
C2 P1 C1 C11 -60.1(2) . . . . ?
Se1 P1 C1 C11 175.2(2) . . . . ?
C01 P1 C1 C12 -77.17(19) . . . . ?
C2 P1 C1 C12 172.59(18) . . . . ?
Se1 P1 C1 C12 47.91(19) . . . . ?
C01 P1 C2 C22 62.95(18) . . . . ?
C1 P1 C2 C22 176.18(16) . . . . ?
Se1 P1 C2 C22 -58.80(17) . . . . ?
C01 P1 C2 C21 -173.87(17) . . . . ?
C1 P1 C2 C21 -60.63(18) . . . . ?
Se1 P1 C2 C21 64.39(17) . . . . ?

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        30.03
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         1.087
_refine_diff_density_min         -0.683
_refine_diff_density_rms         0.074


# end of cif file
####################################################################### 
# 
# 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_nuri
_database_code_depnum_ccdc_archive 'CCDC 1579325'
_audit_update_record             
;
2017-10-11 deposited with the CCDC.
2018-02-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H30 P2 Se2'
_chemical_formula_weight         406.23

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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.0929 2.2259 '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/c'

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

_cell_length_a                   13.7347(4)
_cell_length_b                   10.4735(3)
_cell_length_c                   12.6411(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 100.759(3)
_cell_angle_gamma                90.00
_cell_volume                     1786.46(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    26703
_cell_measurement_theta_min      2.4550
_cell_measurement_theta_max      30.4400

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.510
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             824
_exptl_absorpt_coefficient_mu    4.301
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.75922
_exptl_absorpt_correction_T_max  1.00000
_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) 
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur, Eos'
_diffrn_measurement_method       ω-scan
_diffrn_detector_area_resol_mean 16.1419
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            119830
_diffrn_reflns_av_R_equivalents  0.0521
_diffrn_reflns_av_sigmaI/netI    0.0193
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.46
_diffrn_reflns_theta_max         30.03
_reflns_number_total             5210
_reflns_number_gt                4524
_reflns_threshold_expression     >2sigma(I)

_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_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_reduction        
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.36.28 (release 01-02-2013 CrysAlis171 .NET) 
(compiled Feb  1 2013,16:14:44) 
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker XP'
_computing_publication_material  SHELXL-97

_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.

 The isopropyl group C3, C31, C32 is disordered over two positions, with the
 smaller component being 13% occupied. Suitable restraints were employed to 
 improve refinement stability, but the dimensions of disordered groups
 should always be interpreted with caution. 
;

_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)+(0.0199P)²+1.6274P] 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_number_reflns         5210
_refine_ls_number_parameters     175
_refine_ls_number_restraints     24
_refine_ls_R_factor_all          0.0335
_refine_ls_R_factor_gt           0.0250
_refine_ls_wR_factor_ref         0.0534
_refine_ls_wR_factor_gt          0.0506
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.045
_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
C01 C 0.74318(13) 0.35893(16) 0.76083(13) 0.0168(3) Uani 1 1 d . A .
H01A H 0.7887 0.3102 0.8164 0.020 Uiso 1 1 calc R . .
H01B H 0.6856 0.3832 0.7933 0.020 Uiso 1 1 calc R . .
Se1 Se 0.805244(13) 0.184719(17) 0.564438(13) 0.01837(5) Uani 1 1 d . . .
Se2 Se 0.739075(14) 0.618585(18) 0.606345(15) 0.02363(5) Uani 1 1 d . A .
P1 P 0.69729(3) 0.24714(4) 0.65180(3) 0.01400(8) Uani 1 1 d . . .
C1 C 0.59275(12) 0.32891(17) 0.56715(13) 0.0177(3) Uani 1 1 d . . .
H1 H 0.6214 0.4060 0.5377 0.021 Uiso 1 1 calc R . .
C11 C 0.51568(15) 0.3790(2) 0.62982(16) 0.0285(4) Uani 1 1 d . . .
H11A H 0.4612 0.4193 0.5799 0.043 Uiso 1 1 calc R . .
H11B H 0.5466 0.4419 0.6830 0.043 Uiso 1 1 calc R . .
H11C H 0.4898 0.3078 0.6667 0.043 Uiso 1 1 calc R . .
C12 C 0.54369(15) 0.2511(2) 0.46946(15) 0.0280(4) Uani 1 1 d . . .
H12A H 0.4995 0.1873 0.4919 0.042 Uiso 1 1 calc R . .
H12B H 0.5948 0.2080 0.4379 0.042 Uiso 1 1 calc R . .
H12C H 0.5053 0.3081 0.4158 0.042 Uiso 1 1 calc R . .
C2 C 0.64952(14) 0.11478(16) 0.72426(14) 0.0202(3) Uani 1 1 d . . .
H2 H 0.5958 0.1497 0.7596 0.024 Uiso 1 1 calc R . .
C21 C 0.6049(2) 0.0095(2) 0.64778(18) 0.0423(6) Uani 1 1 d . . .
H21A H 0.6539 -0.0194 0.6057 0.063 Uiso 1 1 calc R . .
H21B H 0.5463 0.0422 0.5990 0.063 Uiso 1 1 calc R . .
H21C H 0.5858 -0.0623 0.6892 0.063 Uiso 1 1 calc R . .
C22 C 0.72962(17) 0.0601(2) 0.81179(16) 0.0322(5) Uani 1 1 d . . .
H22A H 0.7023 -0.0109 0.8475 0.048 Uiso 1 1 calc R . .
H22B H 0.7535 0.1267 0.8648 0.048 Uiso 1 1 calc R . .
H22C H 0.7848 0.0292 0.7796 0.048 Uiso 1 1 calc R . .
P2 P 0.80724(3) 0.50756(4) 0.73892(3) 0.01458(8) Uani 1 1 d D . .
C3 C 0.93236(14) 0.4477(3) 0.73246(16) 0.0185(5) Uani 0.872(6) 1 d PDU A 1
H3 H 0.9225 0.3689 0.6870 0.022 Uiso 0.872(6) 1 calc PR A 1
C31 C 0.99176(16) 0.5403(2) 0.6756(2) 0.0269(6) Uani 0.872(6) 1 d PDU A 1
H31A H 1.0138 0.6127 0.7231 0.040 Uiso 0.872(6) 1 calc PR A 1
H31B H 0.9499 0.5713 0.6092 0.040 Uiso 0.872(6) 1 calc PR A 1
H31C H 1.0496 0.4961 0.6581 0.040 Uiso 0.872(6) 1 calc PR A 1
C32 C 0.9903(2) 0.4060(3) 0.8424(3) 0.0248(6) Uani 0.872(6) 1 d PDU A 1
H32A H 1.0514 0.3628 0.8330 0.037 Uiso 0.872(6) 1 calc PR A 1
H32B H 0.9497 0.3474 0.8763 0.037 Uiso 0.872(6) 1 calc PR A 1
H32C H 1.0069 0.4813 0.8884 0.037 Uiso 0.872(6) 1 calc PR A 1
C3' C 0.9417(8) 0.5062(17) 0.7346(10) 0.015(3) Uiso 0.128(6) 1 d PDU A 2
H3' H 0.9696 0.5904 0.7627 0.018 Uiso 0.128(6) 1 calc PR A 2
C31' C 0.9639(11) 0.4901(15) 0.6223(11) 0.023(4) Uiso 0.128(6) 1 d PDU A 2
H31D H 0.9275 0.5547 0.5745 0.035 Uiso 0.128(6) 1 calc PR A 2
H31E H 0.9432 0.4048 0.5952 0.035 Uiso 0.128(6) 1 calc PR A 2
H31F H 1.0352 0.5004 0.6247 0.035 Uiso 0.128(6) 1 calc PR A 2
C32' C 0.9911(19) 0.404(2) 0.8112(17) 0.032(7) Uiso 0.128(6) 1 d PDU A 2
H32D H 0.9744 0.4173 0.8825 0.048 Uiso 0.128(6) 1 calc PR A 2
H32E H 1.0631 0.4088 0.8167 0.048 Uiso 0.128(6) 1 calc PR A 2
H32F H 0.9676 0.3196 0.7840 0.048 Uiso 0.128(6) 1 calc PR A 2
C4 C 0.80972(13) 0.59263(16) 0.86694(14) 0.0191(3) Uani 1 1 d . A .
H4 H 0.8391 0.5345 0.9272 0.023 Uiso 1 1 calc R . .
C41 C 0.87465(15) 0.71231(18) 0.87273(17) 0.0272(4) Uani 1 1 d . . .
H41A H 0.8489 0.7686 0.8120 0.041 Uiso 1 1 calc R A .
H41B H 0.9428 0.6875 0.8693 0.041 Uiso 1 1 calc R . .
H41C H 0.8738 0.7573 0.9405 0.041 Uiso 1 1 calc R . .
C42 C 0.70481(16) 0.62836(19) 0.88116(17) 0.0293(4) Uani 1 1 d . . .
H42A H 0.7081 0.6753 0.9488 0.044 Uiso 1 1 calc R A .
H42B H 0.6656 0.5505 0.8830 0.044 Uiso 1 1 calc R . .
H42C H 0.6736 0.6821 0.8208 0.044 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
C01 P1 1.8285(17) . ?
C01 P2 1.8345(17) . ?
Se1 P1 2.1111(4) . ?
Se2 P2 2.1099(4) . ?
P1 C1 1.8348(17) . ?
P1 C2 1.8482(17) . ?
C1 C12 1.527(2) . ?
C1 C11 1.528(2) . ?
C2 C21 1.518(3) . ?
C2 C22 1.519(3) . ?
P2 C4 1.8421(17) . ?
P2 C3 1.845(2) . ?
P2 C3' 1.858(11) . ?
C3 C31 1.530(3) . ?
C3 C32 1.530(4) . ?
C3' C31' 1.515(14) . ?
C3' C32' 1.517(16) . ?
C4 C42 1.531(3) . ?
C4 C41 1.532(2) . ?

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
P1 C01 P2 122.48(9) . . ?
C01 P1 C1 105.24(8) . . ?
C01 P1 C2 102.18(8) . . ?
C1 P1 C2 109.12(8) . . ?
C01 P1 Se1 114.56(6) . . ?
C1 P1 Se1 112.90(6) . . ?
C2 P1 Se1 112.08(6) . . ?
C12 C1 C11 111.00(15) . . ?
C12 C1 P1 113.68(13) . . ?
C11 C1 P1 113.58(12) . . ?
C21 C2 C22 109.95(17) . . ?
C21 C2 P1 111.56(13) . . ?
C22 C2 P1 111.59(13) . . ?
C01 P2 C4 102.03(7) . . ?
C01 P2 C3 101.25(10) . . ?
C4 P2 C3 109.79(9) . . ?
C01 P2 C3' 120.4(6) . . ?
C4 P2 C3' 100.0(4) . . ?
C3 P2 C3' 19.4(5) . . ?
C01 P2 Se2 115.68(6) . . ?
C4 P2 Se2 111.34(6) . . ?
C3 P2 Se2 115.53(7) . . ?
C3' P2 Se2 106.1(4) . . ?
C31 C3 C32 112.0(2) . . ?
C31 C3 P2 112.83(16) . . ?
C32 C3 P2 112.77(18) . . ?
C31' C3' C32' 112.1(14) . . ?
C31' C3' P2 113.8(9) . . ?
C32' C3' P2 108.3(13) . . ?
C42 C4 C41 110.27(15) . . ?
C42 C4 P2 110.97(13) . . ?
C41 C4 P2 110.65(13) . . ?

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
P2 C01 P1 C1 -69.87(13) . . . . ?
P2 C01 P1 C2 176.17(11) . . . . ?
P2 C01 P1 Se1 54.73(12) . . . . ?
C01 P1 C1 C12 179.51(13) . . . . ?
C2 P1 C1 C12 -71.47(15) . . . . ?
Se1 P1 C1 C12 53.86(14) . . . . ?
C01 P1 C1 C11 -52.29(15) . . . . ?
C2 P1 C1 C11 56.72(15) . . . . ?
Se1 P1 C1 C11 -177.94(11) . . . . ?
C01 P1 C2 C21 178.89(16) . . . . ?
C1 P1 C2 C21 67.83(17) . . . . ?
Se1 P1 C2 C21 -57.98(17) . . . . ?
C01 P1 C2 C22 -57.68(15) . . . . ?
C1 P1 C2 C22 -168.74(13) . . . . ?
Se1 P1 C2 C22 65.45(14) . . . . ?
P1 C01 P2 C4 168.07(11) . . . . ?
P1 C01 P2 C3 -78.64(13) . . . . ?
P1 C01 P2 C3' -82.6(5) . . . . ?
P1 C01 P2 Se2 47.04(13) . . . . ?
C01 P2 C3 C31 159.34(16) . . . . ?
C4 P2 C3 C31 -93.36(17) . . . . ?
C3' P2 C3 C31 -30.9(11) . . . . ?
Se2 P2 C3 C31 33.56(19) . . . . ?
C01 P2 C3 C32 -72.5(2) . . . . ?
C4 P2 C3 C32 34.8(2) . . . . ?
C3' P2 C3 C32 97.2(12) . . . . ?
Se2 P2 C3 C32 161.71(17) . . . . ?
C01 P2 C3' C31' 92.1(12) . . . . ?
C4 P2 C3' C31' -157.5(11) . . . . ?
C3 P2 C3' C31' 80.4(16) . . . . ?
Se2 P2 C3' C31' -41.6(13) . . . . ?
C01 P2 C3' C32' -33.3(15) . . . . ?
C4 P2 C3' C32' 77.2(14) . . . . ?
C3 P2 C3' C32' -44.9(14) . . . . ?
Se2 P2 C3' C32' -167.0(13) . . . . ?
C01 P2 C4 C42 -65.88(14) . . . . ?
C3 P2 C4 C42 -172.66(14) . . . . ?
C3' P2 C4 C42 169.9(5) . . . . ?
Se2 P2 C4 C42 58.11(14) . . . . ?
C01 P2 C4 C41 171.37(13) . . . . ?
C3 P2 C4 C41 64.59(16) . . . . ?
C3' P2 C4 C41 47.2(5) . . . . ?
Se2 P2 C4 C41 -64.64(14) . . . . ?

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
C4 H4 Se1 1.00 2.97 3.8382(17) 146.4 4_566
C42 H42A Se2 0.98 2.91 3.8534(19) 160.9 4_576

_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full        30.03
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max         1.277
_refine_diff_density_min         -1.049
_refine_diff_density_rms         0.077


# end of cif file
####################################################################### 
# 
# 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_jim
_database_code_depnum_ccdc_archive 'CCDC 1494784'
_audit_update_record             
;
2016-07-19 deposited with the CCDC.
2018-02-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C52 H48 Br24 P4 Se3'
_chemical_formula_weight         2951.50

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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.5395(4)
_cell_length_b                   11.2623(7)
_cell_length_c                   21.3286(8)
_cell_angle_alpha                90.356(4)
_cell_angle_beta                 101.185(4)
_cell_angle_gamma                105.297(4)
_cell_volume                     1937.44(17)
_cell_formula_units_Z            1
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    11169
_cell_measurement_theta_min      2.5120
_cell_measurement_theta_max      28.9050

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.03
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.530
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1362
_exptl_absorpt_coefficient_mu    13.915
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.48740
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) 
(compiled Aug 13 2014,18:06:01) 
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Oxford diffraction Xcalibur, Eos'
_diffrn_measurement_method       ω-scan
_diffrn_detector_area_resol_mean 16.1419
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            101158
_diffrn_reflns_av_R_equivalents  0.0969
_diffrn_reflns_av_sigmaI/netI    0.0586
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         2.17
_diffrn_reflns_theta_max         29.13
_reflns_number_total             10436
_reflns_number_gt                7858
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) 
(compiled Aug 13 2014,18:06:01) 
;
_computing_cell_refinement       
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) 
(compiled Aug 13 2014,18:06:01) 
;
_computing_data_reduction        
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) 
(compiled Aug 13 2014,18:06:01) 
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker XP'
_computing_publication_material  SHELXL-97

_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)+(0.0207P)²+2.9343P] 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_number_reflns         10436
_refine_ls_number_parameters     376
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0668
_refine_ls_R_factor_gt           0.0392
_refine_ls_wR_factor_ref         0.0698
_refine_ls_wR_factor_gt          0.0627
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_refine_ls_shift/su_max          0.003
_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
Br1 Br 0.92363(6) 0.87831(5) 0.61926(2) 0.01919(11) Uani 1 1 d . . .
Br2 Br 0.39402(5) 0.38855(4) 0.63984(2) 0.01306(10) Uani 1 1 d . . .
Br3 Br 0.01669(6) 0.28953(4) 0.54255(2) 0.01481(10) Uani 1 1 d . . .
Br4 Br 0.29885(5) 0.53896(4) 0.48211(2) 0.01336(10) Uani 1 1 d . . .
Br5 Br 0.11275(5) 0.60350(4) 0.61374(2) 0.01265(10) Uani 1 1 d . . .
Br6 Br 0.64495(6) 0.89051(5) 1.02452(2) 0.01993(11) Uani 1 1 d . . .
Br7 Br 0.65509(6) 0.88874(5) 1.15483(2) 0.01804(11) Uani 1 1 d . . .
Br8 Br 0.67288(6) 0.89627(5) 1.26849(2) 0.02391(12) Uani 1 1 d . . .
Br9 Br 0.27049(7) 0.63421(5) 1.04291(2) 0.02357(12) Uani 1 1 d . . .
Br10 Br 0.00014(6) 0.82628(5) 1.01278(2) 0.01720(11) Uani 1 1 d . . .
Br11 Br 0.21255(6) 0.76324(5) 0.88383(2) 0.01657(10) Uani 1 1 d . . .
Br12 Br 0.15057(6) 0.69650(5) 0.76989(2) 0.02221(12) Uani 1 1 d . . .
Se1 Se 0.0000 0.5000 0.5000 0.00945(13) Uani 1 2 d S . .
Se2 Se 0.27757(6) 0.83337(5) 1.01020(2) 0.01440(10) Uani 1 1 d . . .
P1 P 0.69536(15) 0.84817(11) 0.65264(5) 0.0122(2) Uani 1 1 d . . .
P2 P 0.61225(14) 0.47583(11) 0.71052(5) 0.0111(2) Uani 1 1 d . . .
C01 C 0.5954(5) 0.6846(4) 0.6423(2) 0.0132(9) Uani 1 1 d . . .
H01A H 0.4947 0.6659 0.6609 0.016 Uiso 1 1 calc R . .
H01B H 0.5612 0.6592 0.5960 0.016 Uiso 1 1 calc R . .
C02 C 0.7150(5) 0.6120(4) 0.6753(2) 0.0135(9) Uani 1 1 d . . .
H02A H 0.7999 0.6666 0.7091 0.016 Uiso 1 1 calc R . .
H02B H 0.7728 0.5876 0.6434 0.016 Uiso 1 1 calc R . .
C11 C 0.5722(6) 0.9367(4) 0.6102(2) 0.0130(9) Uani 1 1 d . . .
C12 C 0.6412(6) 1.0647(5) 0.6136(2) 0.0199(11) Uani 1 1 d . . .
H12 H 0.7523 1.0995 0.6357 0.024 Uiso 1 1 calc R . .
C13 C 0.5485(6) 1.1398(4) 0.5852(2) 0.0200(11) Uani 1 1 d . . .
H13 H 0.5958 1.2265 0.5870 0.024 Uiso 1 1 calc R . .
C14 C 0.3865(6) 1.0893(5) 0.5541(2) 0.0192(11) Uani 1 1 d . . .
H14 H 0.3223 1.1418 0.5350 0.023 Uiso 1 1 calc R . .
C15 C 0.3168(6) 0.9637(4) 0.5502(2) 0.0183(10) Uani 1 1 d . . .
H15 H 0.2051 0.9302 0.5287 0.022 Uiso 1 1 calc R . .
C16 C 0.4091(6) 0.8863(4) 0.5776(2) 0.0176(10) Uani 1 1 d . . .
H16 H 0.3618 0.7996 0.5743 0.021 Uiso 1 1 calc R . .
C21 C 0.7385(5) 0.8904(4) 0.7360(2) 0.0108(9) Uani 1 1 d . . .
C22 C 0.8936(5) 0.9157(4) 0.7754(2) 0.0128(9) Uani 1 1 d . . .
H22 H 0.9889 0.9181 0.7582 0.015 Uiso 1 1 calc R . .
C23 C 0.9075(6) 0.9375(4) 0.8405(2) 0.0142(10) Uani 1 1 d . . .
H23 H 1.0137 0.9563 0.8680 0.017 Uiso 1 1 calc R . .
C24 C 0.7695(6) 0.9323(4) 0.8657(2) 0.0164(10) Uani 1 1 d . . .
H24 H 0.7809 0.9461 0.9105 0.020 Uiso 1 1 calc R . .
C25 C 0.6131(6) 0.9068(4) 0.8259(2) 0.0165(10) Uani 1 1 d . . .
H25 H 0.5184 0.9035 0.8437 0.020 Uiso 1 1 calc R . .
C26 C 0.5958(6) 0.8863(5) 0.7608(2) 0.0164(10) Uani 1 1 d . . .
H26 H 0.4899 0.8698 0.7332 0.020 Uiso 1 1 calc R . .
C31 C 0.7478(5) 0.3796(4) 0.7306(2) 0.0120(9) Uani 1 1 d . . .
C32 C 0.7431(6) 0.3177(5) 0.7869(2) 0.0176(10) Uani 1 1 d . . .
H32 H 0.6662 0.3248 0.8126 0.021 Uiso 1 1 calc R . .
C33 C 0.8514(6) 0.2458(5) 0.8053(2) 0.0190(11) Uani 1 1 d . . .
H33 H 0.8480 0.2022 0.8432 0.023 Uiso 1 1 calc R . .
C34 C 0.9643(6) 0.2382(4) 0.7680(2) 0.0169(10) Uani 1 1 d . . .
H34 H 1.0411 0.1912 0.7812 0.020 Uiso 1 1 calc R . .
C35 C 0.9668(6) 0.2981(4) 0.7117(2) 0.0162(10) Uani 1 1 d . . .
H35 H 1.0439 0.2907 0.6862 0.019 Uiso 1 1 calc R . .
C36 C 0.8589(5) 0.3682(4) 0.6924(2) 0.0116(9) Uani 1 1 d . . .
H36 H 0.8599 0.4085 0.6534 0.014 Uiso 1 1 calc R . .
C41 C 0.5523(6) 0.5161(4) 0.7817(2) 0.0137(10) Uani 1 1 d . . .
C42 C 0.6744(6) 0.5940(5) 0.8280(2) 0.0215(11) Uani 1 1 d . . .
H42 H 0.7816 0.6300 0.8196 0.026 Uiso 1 1 calc R . .
C43 C 0.6374(7) 0.6187(5) 0.8869(2) 0.0287(13) Uani 1 1 d . . .
H43 H 0.7184 0.6734 0.9185 0.034 Uiso 1 1 calc R . .
C44 C 0.4827(7) 0.5631(5) 0.8989(2) 0.0277(13) Uani 1 1 d . . .
H44 H 0.4585 0.5782 0.9394 0.033 Uiso 1 1 calc R . .
C45 C 0.3627(7) 0.4860(6) 0.8528(3) 0.0301(13) Uani 1 1 d . . .
H45 H 0.2561 0.4493 0.8615 0.036 Uiso 1 1 calc R . .
C46 C 0.3963(6) 0.4619(5) 0.7947(2) 0.0233(12) Uani 1 1 d . . .
H46 H 0.3134 0.4083 0.7632 0.028 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.

 Bromine-bromine contacts etc.: 
 
      3.3783 (0.0007)  Br2 - Br3
      3.4137 (0.0007)  Br5 - Br12
      2.9850 (0.0007)  Se2 - Br6
      3.8611 (0.0007)  Br1 - Br5_$1
      3.8189 (0.0006)  Br2 - Br4
      3.8085 (0.0006)  Br2 - Br5
      3.7394 (0.0007)  Br2 - Br8_$2
      3.7063 (0.0009)  Br4 - Br4_$3
      3.9438 (0.0010)  Br6 - Br6_$4
      3.3520 (0.0007)  Br6 - Br10_$1
      3.1288 (0.0008)  Br6 - Se2_$4
      3.9223 (0.0007)  Br7 - Br11_$4
      3.9185 (0.0007)  Br7 - Se2
      3.9546 (0.0010)  Br10 - Br10_$5


 Operators for generating equivalent atoms:

 $1   x+1, y, z
 $2   -x+1, -y+1, -z+2
 $3   -x+1, -y+1, -z+1
 $4   -x+1, -y+2, -z+2
 $5   -x, -y+2, -z+2

;

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
Br1 P1 2.1481(13) . ?
Br2 P2 2.1534(12) . ?
Br3 Se1 2.5724(5) . ?
Br4 Se1 2.5768(4) . ?
Br5 Se1 2.5764(4) . ?
Br6 Br7 2.7641(7) . ?
Br7 Br8 2.3990(7) . ?
Br9 Se2 2.3421(7) . ?
Br10 Se2 2.3607(6) . ?
Br11 Br12 2.4535(7) . ?
Br11 Se2 2.7126(6) . ?
Se1 Br3 2.5724(5) 2_566 ?
Se1 Br5 2.5764(4) 2_566 ?
Se1 Br4 2.5768(4) 2_566 ?
P1 C11 1.765(5) . ?
P1 C21 1.779(4) . ?
P1 C01 1.807(5) . ?
P2 C31 1.782(5) . ?
P2 C41 1.785(4) . ?
P2 C02 1.802(5) . ?
C01 C02 1.542(6) . ?
C11 C16 1.396(6) . ?
C11 C12 1.401(6) . ?
C12 C13 1.373(6) . ?
C13 C14 1.379(7) . ?
C14 C15 1.377(7) . ?
C15 C16 1.383(6) . ?
C21 C22 1.381(6) . ?
C21 C26 1.410(6) . ?
C22 C23 1.385(6) . ?
C23 C24 1.375(6) . ?
C24 C25 1.393(6) . ?
C25 C26 1.379(6) . ?
C31 C36 1.394(6) . ?
C31 C32 1.395(6) . ?
C32 C33 1.387(6) . ?
C33 C34 1.383(6) . ?
C34 C35 1.381(6) . ?
C35 C36 1.372(6) . ?
C41 C46 1.393(7) . ?
C41 C42 1.393(6) . ?
C42 C43 1.397(7) . ?
C43 C44 1.378(8) . ?
C44 C45 1.378(8) . ?
C45 C46 1.367(7) . ?

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
Br8 Br7 Br6 177.39(3) . . ?
Br12 Br11 Se2 179.03(3) . . ?
Br3 Se1 Br3 180.000(19) . 2_566 ?
Br3 Se1 Br5 90.632(15) . . ?
Br3 Se1 Br5 89.368(15) 2_566 . ?
Br3 Se1 Br5 89.368(15) . 2_566 ?
Br3 Se1 Br5 90.632(15) 2_566 2_566 ?
Br5 Se1 Br5 180.0 . 2_566 ?
Br3 Se1 Br4 89.049(15) . . ?
Br3 Se1 Br4 90.951(15) 2_566 . ?
Br5 Se1 Br4 89.886(14) . . ?
Br5 Se1 Br4 90.114(14) 2_566 . ?
Br3 Se1 Br4 90.951(15) . 2_566 ?
Br3 Se1 Br4 89.049(15) 2_566 2_566 ?
Br5 Se1 Br4 90.114(14) . 2_566 ?
Br5 Se1 Br4 89.886(14) 2_566 2_566 ?
Br4 Se1 Br4 180.0 . 2_566 ?
Br9 Se2 Br10 97.48(3) . . ?
Br9 Se2 Br11 93.67(2) . . ?
Br10 Se2 Br11 94.56(2) . . ?
C11 P1 C21 109.9(2) . . ?
C11 P1 C01 112.7(2) . . ?
C21 P1 C01 107.5(2) . . ?
C11 P1 Br1 109.77(16) . . ?
C21 P1 Br1 109.67(15) . . ?
C01 P1 Br1 107.24(16) . . ?
C31 P2 C41 108.5(2) . . ?
C31 P2 C02 110.0(2) . . ?
C41 P2 C02 110.7(2) . . ?
C31 P2 Br2 112.75(15) . . ?
C41 P2 Br2 109.39(16) . . ?
C02 P2 Br2 105.44(15) . . ?
C02 C01 P1 110.1(3) . . ?
C01 C02 P2 113.1(3) . . ?
C16 C11 C12 119.6(4) . . ?
C16 C11 P1 123.3(4) . . ?
C12 C11 P1 117.0(4) . . ?
C13 C12 C11 120.1(5) . . ?
C12 C13 C14 119.9(5) . . ?
C15 C14 C13 120.8(4) . . ?
C14 C15 C16 120.2(4) . . ?
C15 C16 C11 119.4(4) . . ?
C22 C21 C26 121.3(4) . . ?
C22 C21 P1 124.8(3) . . ?
C26 C21 P1 113.7(3) . . ?
C21 C22 C23 118.8(4) . . ?
C24 C23 C22 120.8(4) . . ?
C23 C24 C25 120.4(4) . . ?
C26 C25 C24 120.0(4) . . ?
C25 C26 C21 118.7(4) . . ?
C36 C31 C32 120.5(4) . . ?
C36 C31 P2 121.5(3) . . ?
C32 C31 P2 118.0(3) . . ?
C33 C32 C31 119.6(4) . . ?
C34 C33 C32 119.4(4) . . ?
C35 C34 C33 120.8(4) . . ?
C36 C35 C34 120.6(4) . . ?
C35 C36 C31 119.2(4) . . ?
C46 C41 C42 120.1(4) . . ?
C46 C41 P2 122.3(4) . . ?
C42 C41 P2 117.2(4) . . ?
C41 C42 C43 119.2(5) . . ?
C44 C43 C42 119.6(5) . . ?
C45 C44 C43 120.8(5) . . ?
C46 C45 C44 120.3(5) . . ?
C45 C46 C41 119.9(5) . . ?

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        29.13
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         1.045
_refine_diff_density_min         -0.930
_refine_diff_density_rms         0.198


# start Validation Reply Form
_vrf_PLAT431_jim                 
;
PROBLEM: Short Inter HL..A Contact Br6 .. Se2 .. 2.98 Ang.
RESPONSE: We have noticed the short contacts
 and they are mentioned in the paper!
;
# end Validation Reply Form

# end of cif file
####################################################################### 
# 
# 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_elias
_database_code_depnum_ccdc_archive 'CCDC 1494786'
_audit_update_record             
;
2016-07-19 deposited with the CCDC.
2018-02-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H24 I4 P2 Se2'
_chemical_formula_weight         1063.91

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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 '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/n'

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

_cell_length_a                   10.1210(2)
_cell_length_b                   17.1331(4)
_cell_length_c                   17.6880(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.514(2)
_cell_angle_gamma                90.00
_cell_volume                     3067.03(12)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    21787
_cell_measurement_theta_min      2.5790
_cell_measurement_theta_max      30.7350

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.2
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.304
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1960
_exptl_absorpt_coefficient_mu    6.557
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.44249
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
'Mon Oct 19 16:40:45 2015'
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           'Mo K\a'
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur, Eos'
_diffrn_measurement_method       'ω scan'
_diffrn_detector_area_resol_mean 16.1419
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            80670
_diffrn_reflns_av_R_equivalents  0.0419
_diffrn_reflns_av_sigmaI/netI    0.0253
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.30
_diffrn_reflns_theta_max         31.10
_reflns_number_total             9266
_reflns_number_gt                8092
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
'Mon Oct 19 16:40:45 2015'
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_cell_refinement       
;
'Mon Oct 19 16:40:45 2015'
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
'Mon Oct 19 16:40:45 2015'
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker XP'
_computing_publication_material  SHELXL-97

_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)+(0.0129P)²+3.4719P] 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_number_reflns         9266
_refine_ls_number_parameters     307
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0338
_refine_ls_R_factor_gt           0.0256
_refine_ls_wR_factor_ref         0.0481
_refine_ls_wR_factor_gt          0.0459
_refine_ls_goodness_of_fit_ref   1.139
_refine_ls_restrained_S_all      1.139
_refine_ls_shift/su_max          0.003
_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
I1 I 0.016294(16) 0.737055(10) 0.399662(9) 0.01550(4) Uani 1 1 d . . .
I2 I 0.005157(19) 0.901310(10) 0.404660(10) 0.02106(4) Uani 1 1 d . . .
I3 I 0.664504(16) 0.602613(10) 0.269965(9) 0.01583(4) Uani 1 1 d . . .
I4 I 0.656858(18) 0.608125(11) 0.110239(10) 0.02105(4) Uani 1 1 d . . .
Se1 Se 0.01059(3) 0.567421(15) 0.407015(14) 0.01551(6) Uani 1 1 d . . .
Se2 Se 0.66674(3) 0.593842(15) 0.433036(14) 0.01502(5) Uani 1 1 d . . .
P1 P 0.16849(6) 0.52609(4) 0.33671(3) 0.01037(12) Uani 1 1 d . . .
P2 P 0.48881(6) 0.65993(4) 0.45027(3) 0.01049(12) Uani 1 1 d . . .
C1 C 0.3297(2) 0.54350(14) 0.38018(13) 0.0114(5) Uani 1 1 d . . .
H1A H 0.3319 0.5204 0.4315 0.014 Uiso 1 1 calc R . .
H1B H 0.3990 0.5179 0.3498 0.014 Uiso 1 1 calc R . .
C2 C 0.3579(2) 0.63135(14) 0.38532(13) 0.0114(5) Uani 1 1 d . . .
H2A H 0.2756 0.6581 0.4005 0.014 Uiso 1 1 calc R . .
H2B H 0.3807 0.6504 0.3342 0.014 Uiso 1 1 calc R . .
C11 C 0.1502(2) 0.42188(14) 0.32589(14) 0.0124(5) Uani 1 1 d . . .
C12 C 0.1774(3) 0.38573(15) 0.25686(15) 0.0181(5) Uani 1 1 d . . .
H12 H 0.2064 0.4158 0.2151 0.022 Uiso 1 1 calc R . .
C13 C 0.1618(3) 0.30600(15) 0.24983(16) 0.0224(6) Uani 1 1 d . . .
H13 H 0.1814 0.2812 0.2032 0.027 Uiso 1 1 calc R . .
C14 C 0.1177(3) 0.26191(16) 0.31023(16) 0.0218(6) Uani 1 1 d . . .
H14 H 0.1043 0.2073 0.3044 0.026 Uiso 1 1 calc R . .
C15 C 0.0931(3) 0.29726(16) 0.37896(16) 0.0219(6) Uani 1 1 d . . .
H15 H 0.0650 0.2667 0.4207 0.026 Uiso 1 1 calc R . .
C16 C 0.1093(3) 0.37695(15) 0.38719(15) 0.0175(5) Uani 1 1 d . . .
H16 H 0.0926 0.4011 0.4345 0.021 Uiso 1 1 calc R . .
C21 C 0.1687(2) 0.56913(14) 0.24359(13) 0.0122(5) Uani 1 1 d . . .
C22 C 0.0566(3) 0.60872(14) 0.21772(15) 0.0153(5) Uani 1 1 d . . .
H22 H -0.0166 0.6161 0.2502 0.018 Uiso 1 1 calc R . .
C23 C 0.0527(3) 0.63730(15) 0.14397(15) 0.0185(5) Uani 1 1 d . . .
H23 H -0.0228 0.6651 0.1263 0.022 Uiso 1 1 calc R . .
C24 C 0.1589(3) 0.62518(16) 0.09636(14) 0.0184(5) Uani 1 1 d . . .
H24 H 0.1555 0.6443 0.0459 0.022 Uiso 1 1 calc R . .
C25 C 0.2699(3) 0.58540(15) 0.12187(15) 0.0172(5) Uani 1 1 d . . .
H25 H 0.3420 0.5769 0.0888 0.021 Uiso 1 1 calc R . .
C26 C 0.2760(3) 0.55795(14) 0.19554(14) 0.0142(5) Uani 1 1 d . . .
H26 H 0.3528 0.5316 0.2133 0.017 Uiso 1 1 calc R . .
C31 C 0.5059(2) 0.76405(14) 0.43417(13) 0.0115(5) Uani 1 1 d . . .
C32 C 0.4038(3) 0.81302(15) 0.45792(14) 0.0149(5) Uani 1 1 d . . .
H32 H 0.3295 0.7919 0.4832 0.018 Uiso 1 1 calc R . .
C33 C 0.4116(3) 0.89282(15) 0.44429(15) 0.0173(5) Uani 1 1 d . . .
H33 H 0.3426 0.9264 0.4604 0.021 Uiso 1 1 calc R . .
C34 C 0.5199(3) 0.92335(16) 0.40723(15) 0.0199(6) Uani 1 1 d . . .
H34 H 0.5251 0.9779 0.3981 0.024 Uiso 1 1 calc R . .
C35 C 0.6210(3) 0.87460(16) 0.38330(15) 0.0203(6) Uani 1 1 d . . .
H35 H 0.6947 0.8959 0.3576 0.024 Uiso 1 1 calc R . .
C36 C 0.6146(3) 0.79471(15) 0.39698(14) 0.0157(5) Uani 1 1 d . . .
H36 H 0.6840 0.7614 0.3810 0.019 Uiso 1 1 calc R . .
C41 C 0.4310(3) 0.64822(14) 0.54557(13) 0.0124(5) Uani 1 1 d . . .
C42 C 0.3003(3) 0.63085(17) 0.56218(15) 0.0210(6) Uani 1 1 d . . .
H42 H 0.2381 0.6230 0.5224 0.025 Uiso 1 1 calc R . .
C43 C 0.2605(3) 0.62490(19) 0.63689(16) 0.0270(7) Uani 1 1 d . . .
H43 H 0.1715 0.6122 0.6483 0.032 Uiso 1 1 calc R . .
C44 C 0.3510(3) 0.63752(19) 0.69456(16) 0.0276(7) Uani 1 1 d . . .
H44 H 0.3235 0.6340 0.7456 0.033 Uiso 1 1 calc R . .
C45 C 0.4806(3) 0.65513(18) 0.67887(15) 0.0240(6) Uani 1 1 d . . .
H45 H 0.5419 0.6637 0.7190 0.029 Uiso 1 1 calc R . .
C46 C 0.5214(3) 0.66038(15) 0.60449(14) 0.0165(5) Uani 1 1 d . . .
H46 H 0.6109 0.6723 0.5936 0.020 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
I1 I2 2.8179(2) . ?
I1 Se1 2.9098(3) . ?
I3 I4 2.8272(2) . ?
I3 Se2 2.8882(3) . ?
Se1 P1 2.1534(7) . ?
Se2 P2 2.1512(7) . ?
P1 C21 1.805(2) . ?
P1 C11 1.805(2) . ?
P1 C1 1.822(2) . ?
P2 C41 1.800(2) . ?
P2 C2 1.813(2) . ?
P2 C31 1.815(2) . ?
C1 C2 1.534(3) . ?
C11 C16 1.396(4) . ?
C11 C12 1.399(3) . ?
C12 C13 1.381(4) . ?
C13 C14 1.386(4) . ?
C14 C15 1.383(4) . ?
C15 C16 1.383(4) . ?
C21 C22 1.395(3) . ?
C21 C26 1.398(3) . ?
C22 C23 1.394(4) . ?
C23 C24 1.387(4) . ?
C24 C25 1.386(4) . ?
C25 C26 1.386(3) . ?
C31 C36 1.390(3) . ?
C31 C32 1.399(3) . ?
C32 C33 1.391(4) . ?
C33 C34 1.385(4) . ?
C34 C35 1.390(4) . ?
C35 C36 1.392(4) . ?
C41 C42 1.390(4) . ?
C41 C46 1.396(3) . ?
C42 C43 1.389(4) . ?
C43 C44 1.382(4) . ?
C44 C45 1.376(4) . ?
C45 C46 1.386(4) . ?

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
I2 I1 Se1 174.428(9) . . ?
I4 I3 Se2 178.454(9) . . ?
P1 Se1 I1 106.707(19) . . ?
P2 Se2 I3 96.606(19) . . ?
C21 P1 C11 107.96(11) . . ?
C21 P1 C1 108.05(11) . . ?
C11 P1 C1 107.29(11) . . ?
C21 P1 Se1 113.56(9) . . ?
C11 P1 Se1 108.09(9) . . ?
C1 P1 Se1 111.65(8) . . ?
C41 P2 C2 108.73(12) . . ?
C41 P2 C31 106.78(11) . . ?
C2 P2 C31 103.66(11) . . ?
C41 P2 Se2 110.71(8) . . ?
C2 P2 Se2 112.09(8) . . ?
C31 P2 Se2 114.46(8) . . ?
C2 C1 P1 110.54(16) . . ?
C1 C2 P2 115.90(17) . . ?
C16 C11 C12 119.7(2) . . ?
C16 C11 P1 119.61(19) . . ?
C12 C11 P1 120.66(19) . . ?
C13 C12 C11 119.6(2) . . ?
C12 C13 C14 120.5(3) . . ?
C15 C14 C13 120.1(3) . . ?
C16 C15 C14 120.2(3) . . ?
C15 C16 C11 119.9(2) . . ?
C22 C21 C26 120.1(2) . . ?
C22 C21 P1 119.35(19) . . ?
C26 C21 P1 120.40(19) . . ?
C23 C22 C21 119.6(2) . . ?
C24 C23 C22 120.0(2) . . ?
C25 C24 C23 120.4(2) . . ?
C26 C25 C24 120.1(2) . . ?
C25 C26 C21 119.8(2) . . ?
C36 C31 C32 120.4(2) . . ?
C36 C31 P2 121.51(19) . . ?
C32 C31 P2 118.08(19) . . ?
C33 C32 C31 119.6(2) . . ?
C34 C33 C32 120.0(2) . . ?
C33 C34 C35 120.3(3) . . ?
C34 C35 C36 120.2(3) . . ?
C31 C36 C35 119.5(2) . . ?
C42 C41 C46 119.5(2) . . ?
C42 C41 P2 122.7(2) . . ?
C46 C41 P2 117.75(19) . . ?
C43 C42 C41 120.1(3) . . ?
C44 C43 C42 119.7(3) . . ?
C45 C44 C43 120.8(3) . . ?
C44 C45 C46 119.9(3) . . ?
C45 C46 C41 120.0(3) . . ?

_diffrn_measured_fraction_theta_max 0.939
_diffrn_reflns_theta_full        30.00
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         1.041
_refine_diff_density_min         -0.632
_refine_diff_density_rms         0.125


# end of cif file
####################################################################### 
# 
# 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_theo
_database_code_depnum_ccdc_archive 'CCDC 1494785'
_audit_update_record             
;
2016-07-19 deposited with the CCDC.
2018-02-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H22 I4 P2 Se2'
_chemical_formula_weight         1049.89

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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
I I -0.4742 1.8119 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.4770(4)
_cell_length_b                   9.7121(5)
_cell_length_c                   17.9114(7)
_cell_angle_alpha                93.546(4)
_cell_angle_beta                 93.715(3)
_cell_angle_gamma                110.679(4)
_cell_volume                     1532.79(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    25356
_cell_measurement_theta_min      2.6030
_cell_measurement_theta_max      30.5570

_exptl_crystal_description       plate
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.01
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.275
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             964
_exptl_absorpt_coefficient_mu    6.558
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.58518
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) 
(compiled Aug 13 2014,18:06:01) 
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           'Mo K\a'
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur, Eos'
_diffrn_measurement_method       'ω scan'
_diffrn_detector_area_resol_mean 16.1419
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            82122
_diffrn_reflns_av_R_equivalents  0.0378
_diffrn_reflns_av_sigmaI/netI    0.0232
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         2.25
_diffrn_reflns_theta_max         31.11
_reflns_number_total             9098
_reflns_number_gt                7987
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) 
(compiled Aug 13 2014,18:06:01) 
;
_computing_cell_refinement       
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) 
(compiled Aug 13 2014,18:06:01) 
;
_computing_data_reduction        
; 
CrysAlisPro, Agilent Technologies, 
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) 
(compiled Aug 13 2014,18:06:01) 
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker XP'
_computing_publication_material  SHELXL-97

_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)+(0.0140P)²+1.5439P] 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_number_reflns         9098
_refine_ls_number_parameters     298
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0285
_refine_ls_R_factor_gt           0.0218
_refine_ls_wR_factor_ref         0.0429
_refine_ls_wR_factor_gt          0.0408
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0.002
_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
I1 I 0.773714(19) 0.51291(2) 0.457947(9) 0.02755(4) Uani 1 1 d . . .
I2 I 0.111931(17) -0.059253(19) 0.247958(9) 0.02396(4) Uani 1 1 d . . .
I3 I 0.443293(15) 0.077813(15) 0.248168(8) 0.01476(3) Uani 1 1 d . . .
I4 I 0.766082(16) 0.189537(16) 0.236077(9) 0.02020(4) Uani 1 1 d . . .
Se1 Se 0.73763(2) 0.52663(3) 0.311035(12) 0.01534(5) Uani 1 1 d . . .
Se2 Se 0.70339(3) 0.51741(3) 0.151952(13) 0.01860(5) Uani 1 1 d . . .
P1 P 0.61231(6) 0.68201(6) 0.32282(3) 0.01186(10) Uani 1 1 d . . .
P2 P 0.57639(6) 0.65960(6) 0.14983(3) 0.01228(10) Uani 1 1 d . . .
C01 C 0.6266(2) 0.7771(2) 0.23805(11) 0.0131(4) Uani 1 1 d . . .
H01A H 0.7321 0.8470 0.2381 0.016 Uiso 1 1 calc R . .
H01B H 0.5604 0.8362 0.2398 0.016 Uiso 1 1 calc R . .
C11 C 0.6846(2) 0.8240(2) 0.39963(12) 0.0156(4) Uani 1 1 d . . .
C12 C 0.8138(3) 0.9470(3) 0.39415(13) 0.0220(5) Uani 1 1 d . . .
H12 H 0.8658 0.9560 0.3501 0.026 Uiso 1 1 calc R . .
C13 C 0.8661(3) 1.0566(3) 0.45339(15) 0.0304(6) Uani 1 1 d . . .
H13 H 0.9537 1.1414 0.4498 0.037 Uiso 1 1 calc R . .
C14 C 0.7908(3) 1.0424(3) 0.51751(16) 0.0344(6) Uani 1 1 d . . .
H14 H 0.8268 1.1179 0.5579 0.041 Uiso 1 1 calc R . .
C15 C 0.6636(3) 0.9193(3) 0.52352(15) 0.0341(6) Uani 1 1 d . . .
H15 H 0.6130 0.9101 0.5681 0.041 Uiso 1 1 calc R . .
C16 C 0.6095(3) 0.8087(3) 0.46442(14) 0.0252(5) Uani 1 1 d . . .
H16 H 0.5223 0.7238 0.4683 0.030 Uiso 1 1 calc R . .
C21 C 0.4162(2) 0.5825(2) 0.33284(12) 0.0142(4) Uani 1 1 d . . .
C22 C 0.3610(3) 0.4309(3) 0.33732(14) 0.0210(5) Uani 1 1 d . . .
H22 H 0.4270 0.3768 0.3345 0.025 Uiso 1 1 calc R . .
C23 C 0.2087(3) 0.3589(3) 0.34589(15) 0.0264(5) Uani 1 1 d . . .
H23 H 0.1702 0.2550 0.3487 0.032 Uiso 1 1 calc R . .
C24 C 0.1130(3) 0.4375(3) 0.35040(14) 0.0242(5) Uani 1 1 d . . .
H24 H 0.0092 0.3877 0.3570 0.029 Uiso 1 1 calc R . .
C25 C 0.1676(3) 0.5886(3) 0.34532(15) 0.0254(5) Uani 1 1 d . . .
H25 H 0.1009 0.6419 0.3480 0.030 Uiso 1 1 calc R . .
C26 C 0.3192(3) 0.6622(3) 0.33639(15) 0.0229(5) Uani 1 1 d . . .
H26 H 0.3569 0.7658 0.3327 0.027 Uiso 1 1 calc R . .
C31 C 0.3744(2) 0.5654(2) 0.13956(12) 0.0145(4) Uani 1 1 d . . .
C32 C 0.2781(3) 0.6460(3) 0.13979(14) 0.0208(5) Uani 1 1 d . . .
H32 H 0.3193 0.7507 0.1484 0.025 Uiso 1 1 calc R . .
C33 C 0.1234(3) 0.5739(3) 0.12752(15) 0.0266(5) Uani 1 1 d . . .
H33 H 0.0582 0.6291 0.1267 0.032 Uiso 1 1 calc R . .
C34 C 0.0633(3) 0.4211(3) 0.11644(16) 0.0306(6) Uani 1 1 d . . .
H34 H -0.0431 0.3717 0.1073 0.037 Uiso 1 1 calc R . .
C35 C 0.1577(3) 0.3400(3) 0.11866(18) 0.0346(7) Uani 1 1 d . . .
H35 H 0.1157 0.2351 0.1126 0.041 Uiso 1 1 calc R . .
C36 C 0.3136(3) 0.4120(3) 0.12979(15) 0.0254(5) Uani 1 1 d . . .
H36 H 0.3786 0.3566 0.1307 0.030 Uiso 1 1 calc R . .
C41 C 0.6232(2) 0.7845(2) 0.07734(12) 0.0142(4) Uani 1 1 d . . .
C42 C 0.5187(3) 0.7714(3) 0.01647(13) 0.0187(5) Uani 1 1 d . . .
H42 H 0.4201 0.6979 0.0136 0.022 Uiso 1 1 calc R . .
C43 C 0.5589(3) 0.8660(3) -0.03998(14) 0.0242(5) Uani 1 1 d . . .
H43 H 0.4876 0.8572 -0.0815 0.029 Uiso 1 1 calc R . .
C44 C 0.7022(3) 0.9729(3) -0.03597(14) 0.0236(5) Uani 1 1 d . . .
H44 H 0.7291 1.0377 -0.0746 0.028 Uiso 1 1 calc R . .
C45 C 0.8064(3) 0.9856(3) 0.02415(14) 0.0252(5) Uani 1 1 d . . .
H45 H 0.9048 1.0592 0.0267 0.030 Uiso 1 1 calc R . .
C46 C 0.7679(3) 0.8913(3) 0.08082(13) 0.0218(5) Uani 1 1 d . . .
H46 H 0.8402 0.8997 0.1218 0.026 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. 

 Short contacts:

      3.5666 (0.0003)  Se1 - I2
      3.8180 (0.0003)  Se2 - I2
                                 
;

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
I1 Se1 2.6491(3) . ?
I2 I3 2.9460(3) . ?
I3 I4 2.8901(2) . ?
Se1 P1 2.2341(6) . ?
Se1 Se2 2.8391(3) . ?
Se2 P2 2.1287(6) . ?
P1 C21 1.793(2) . ?
P1 C11 1.800(2) . ?
P1 C01 1.814(2) . ?
P2 C31 1.798(2) . ?
P2 C41 1.801(2) . ?
P2 C01 1.822(2) . ?
C11 C16 1.389(3) . ?
C11 C12 1.390(3) . ?
C12 C13 1.387(3) . ?
C13 C14 1.379(4) . ?
C14 C15 1.382(4) . ?
C15 C16 1.392(3) . ?
C21 C22 1.387(3) . ?
C21 C26 1.397(3) . ?
C22 C23 1.387(3) . ?
C23 C24 1.380(4) . ?
C24 C25 1.384(4) . ?
C25 C26 1.386(3) . ?
C31 C36 1.389(3) . ?
C31 C32 1.395(3) . ?
C32 C33 1.379(3) . ?
C33 C34 1.385(4) . ?
C34 C35 1.385(4) . ?
C35 C36 1.389(3) . ?
C41 C46 1.392(3) . ?
C41 C42 1.393(3) . ?
C42 C43 1.389(3) . ?
C43 C44 1.382(4) . ?
C44 C45 1.382(3) . ?
C45 C46 1.389(3) . ?

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
I4 I3 I2 174.125(7) . . ?
P1 Se1 I1 93.254(17) . . ?
P1 Se1 Se2 91.478(16) . . ?
I1 Se1 Se2 174.940(11) . . ?
P2 Se2 Se1 94.891(17) . . ?
C21 P1 C11 107.98(10) . . ?
C21 P1 C01 108.85(10) . . ?
C11 P1 C01 106.10(10) . . ?
C21 P1 Se1 110.54(8) . . ?
C11 P1 Se1 115.34(7) . . ?
C01 P1 Se1 107.79(7) . . ?
C31 P2 C41 107.48(10) . . ?
C31 P2 C01 108.08(10) . . ?
C41 P2 C01 105.39(10) . . ?
C31 P2 Se2 114.50(8) . . ?
C41 P2 Se2 113.07(7) . . ?
C01 P2 Se2 107.83(7) . . ?
P1 C01 P2 115.84(12) . . ?
C16 C11 C12 120.5(2) . . ?
C16 C11 P1 119.01(18) . . ?
C12 C11 P1 120.45(17) . . ?
C13 C12 C11 119.6(2) . . ?
C14 C13 C12 120.0(3) . . ?
C13 C14 C15 120.6(2) . . ?
C14 C15 C16 120.1(3) . . ?
C11 C16 C15 119.2(2) . . ?
C22 C21 C26 120.4(2) . . ?
C22 C21 P1 121.59(17) . . ?
C26 C21 P1 118.06(17) . . ?
C21 C22 C23 119.5(2) . . ?
C24 C23 C22 120.3(2) . . ?
C23 C24 C25 120.3(2) . . ?
C24 C25 C26 120.2(2) . . ?
C25 C26 C21 119.4(2) . . ?
C36 C31 C32 119.8(2) . . ?
C36 C31 P2 119.98(17) . . ?
C32 C31 P2 120.22(17) . . ?
C33 C32 C31 120.2(2) . . ?
C32 C33 C34 119.9(2) . . ?
C33 C34 C35 120.4(2) . . ?
C34 C35 C36 120.0(2) . . ?
C35 C36 C31 119.8(2) . . ?
C46 C41 C42 119.8(2) . . ?
C46 C41 P2 119.35(17) . . ?
C42 C41 P2 120.80(17) . . ?
C43 C42 C41 119.8(2) . . ?
C44 C43 C42 120.2(2) . . ?
C45 C44 C43 120.0(2) . . ?
C44 C45 C46 120.3(2) . . ?
C45 C46 C41 119.8(2) . . ?

_diffrn_measured_fraction_theta_max 0.924
_diffrn_reflns_theta_full        30.00
_diffrn_measured_fraction_theta_full 0.982
_refine_diff_density_max         1.409
_refine_diff_density_min         -1.461
_refine_diff_density_rms         0.118


# end of cif file
####################################################################### 
# 
# 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_joerg
_database_code_depnum_ccdc_archive 'CCDC 1494787'
_audit_update_record             
;
2016-07-19 deposited with the CCDC.
2018-02-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C25 H22.14 Br3.86 P2 S'
_chemical_formula_weight         725.32

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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 2/c'

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

_cell_length_a                   33.378(2)
_cell_length_b                   9.7846(6)
_cell_length_c                   16.5575(9)
_cell_angle_alpha                90.00
_cell_angle_beta                 102.100(6)
_cell_angle_gamma                90.00
_cell_volume                     5287.4(5)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    8793
_cell_measurement_theta_min      2.4920
_cell_measurement_theta_max      28.6930

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.1
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.822
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2826
_exptl_absorpt_coefficient_mu    6.096
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.76183
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           'Mo K\a'
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur, Eos'
_diffrn_measurement_method       'ω scan'
_diffrn_detector_area_resol_mean 16.1419
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            64092
_diffrn_reflns_av_R_equivalents  0.0723
_diffrn_reflns_av_sigmaI/netI    0.0405
_diffrn_reflns_limit_h_min       -44
_diffrn_reflns_limit_h_max       44
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.17
_diffrn_reflns_theta_max         28.70
_reflns_number_total             6831
_reflns_number_gt                5433
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker XP'
_computing_publication_material  SHELXL-97

_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.

 The second tribromide site is overlaid by an assumed HBr2 anion, the H
 atom of which was not located.
;

_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)+(0.0238P)²+14.6355P] 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_number_reflns         6831
_refine_ls_number_parameters     301
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0580
_refine_ls_R_factor_gt           0.0389
_refine_ls_wR_factor_ref         0.0754
_refine_ls_wR_factor_gt          0.0701
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.051
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Br1 Br 0.179905(10) 0.10450(4) 0.27420(2) 0.03140(9) Uani 1 1 d . . .
Br2 Br 0.194925(11) 0.09711(3) 0.53778(2) 0.03153(9) Uani 1 1 d . . .
Br3 Br 0.2500 0.2500 0.5000 0.02615(11) Uani 1 2 d S . .
Br4 Br 0.0000 -0.05601(6) 0.2500 0.02267(16) Uani 0.7269(12) 2 d SP . 1
Br5 Br 0.076098(19) -0.06043(5) 0.31188(3) 0.02839(16) Uani 0.7269(12) 1 d P .
1
Br6 Br 0.04701(5) -0.05296(13) 0.31628(7) 0.0272(4) Uani 0.2731(12) 1 d P . 2
S1 S 0.05358(2) 0.49793(9) 0.30801(5) 0.02601(18) Uani 1 1 d . . .
P1 P 0.09547(2) 0.41568(8) 0.39369(4) 0.01687(16) Uani 1 1 d . . .
P2 P 0.13615(2) 0.27137(9) 0.26464(4) 0.01927(17) Uani 1 1 d . . .
C01 C 0.11885(9) 0.2619(3) 0.36026(16) 0.0189(6) Uani 1 1 d . . .
H01A H 0.1426 0.2365 0.4044 0.023 Uiso 1 1 calc R . .
H01B H 0.0987 0.1866 0.3556 0.023 Uiso 1 1 calc R . .
C11 C 0.13770(9) 0.5285(3) 0.43530(19) 0.0222(7) Uani 1 1 d . . .
C12 C 0.16765(9) 0.4891(3) 0.50272(19) 0.0246(7) Uani 1 1 d . . .
H12 H 0.1670 0.4002 0.5255 0.030 Uiso 1 1 calc R . .
C13 C 0.19849(10) 0.5794(4) 0.5368(2) 0.0330(8) Uani 1 1 d . . .
H13 H 0.2192 0.5520 0.5824 0.040 Uiso 1 1 calc R . .
C14 C 0.19918(11) 0.7103(4) 0.5043(3) 0.0382(9) Uani 1 1 d . . .
H14 H 0.2199 0.7730 0.5287 0.046 Uiso 1 1 calc R . .
C15 C 0.16992(12) 0.7489(4) 0.4370(2) 0.0376(9) Uani 1 1 d . . .
H15 H 0.1708 0.8379 0.4144 0.045 Uiso 1 1 calc R . .
C16 C 0.13897(11) 0.6592(3) 0.4016(2) 0.0281(7) Uani 1 1 d . . .
H16 H 0.1188 0.6863 0.3548 0.034 Uiso 1 1 calc R . .
C21 C 0.07679(8) 0.3571(3) 0.48259(16) 0.0150(6) Uani 1 1 d . . .
C22 C 0.05408(9) 0.4526(3) 0.51730(17) 0.0177(6) Uani 1 1 d . . .
H22 H 0.0488 0.5404 0.4929 0.021 Uiso 1 1 calc R . .
C23 C 0.03923(9) 0.4198(3) 0.58714(17) 0.0205(6) Uani 1 1 d . . .
H23 H 0.0239 0.4848 0.6106 0.025 Uiso 1 1 calc R . .
C24 C 0.04697(9) 0.2918(3) 0.62237(18) 0.0228(7) Uani 1 1 d . . .
H24 H 0.0371 0.2695 0.6705 0.027 Uiso 1 1 calc R . .
C25 C 0.06896(10) 0.1958(3) 0.58819(17) 0.0216(6) Uani 1 1 d . . .
H25 H 0.0738 0.1078 0.6126 0.026 Uiso 1 1 calc R . .
C26 C 0.08404(9) 0.2278(3) 0.51815(17) 0.0197(6) Uani 1 1 d . . .
H26 H 0.0992 0.1620 0.4947 0.024 Uiso 1 1 calc R . .
C31 C 0.09758(9) 0.2368(3) 0.17464(17) 0.0210(6) Uani 1 1 d . . .
C32 C 0.11061(11) 0.2162(3) 0.10113(19) 0.0282(7) Uani 1 1 d . . .
H32 H 0.1387 0.2267 0.0994 0.034 Uiso 1 1 calc R . .
C33 C 0.08236(11) 0.1803(4) 0.03035(19) 0.0310(8) Uani 1 1 d . . .
H33 H 0.0911 0.1653 -0.0200 0.037 Uiso 1 1 calc R . .
C34 C 0.04146(11) 0.1663(3) 0.03339(19) 0.0285(8) Uani 1 1 d . . .
H34 H 0.0221 0.1415 -0.0151 0.034 Uiso 1 1 calc R . .
C35 C 0.02854(10) 0.1882(3) 0.1063(2) 0.0269(7) Uani 1 1 d . . .
H35 H 0.0003 0.1795 0.1074 0.032 Uiso 1 1 calc R . .
C36 C 0.05642(9) 0.2227(3) 0.17775(19) 0.0234(7) Uani 1 1 d . . .
H36 H 0.0476 0.2365 0.2281 0.028 Uiso 1 1 calc R . .
C41 C 0.16380(9) 0.4244(3) 0.25498(17) 0.0209(6) Uani 1 1 d . . .
C42 C 0.20350(9) 0.4430(4) 0.30216(18) 0.0238(7) Uani 1 1 d . . .
H42 H 0.2164 0.3722 0.3375 0.029 Uiso 1 1 calc R . .
C43 C 0.22357(10) 0.5642(4) 0.29699(19) 0.0295(8) Uani 1 1 d . . .
H43 H 0.2505 0.5772 0.3289 0.035 Uiso 1 1 calc R . .
C44 C 0.20474(10) 0.6682(4) 0.24519(19) 0.0290(8) Uani 1 1 d . . .
H44 H 0.2189 0.7514 0.2413 0.035 Uiso 1 1 calc R . .
C45 C 0.16544(10) 0.6498(4) 0.19944(19) 0.0297(8) Uani 1 1 d . . .
H45 H 0.1525 0.7213 0.1646 0.036 Uiso 1 1 calc R . .
C46 C 0.14466(10) 0.5281(4) 0.20380(18) 0.0254(7) Uani 1 1 d . . .
H46 H 0.1177 0.5158 0.1722 0.030 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
Br1 P2 2.1742(9) . ?
Br2 Br3 2.5476(4) . ?
Br3 Br2 2.5476(4) 7_556 ?
Br4 Br5 2.5322(6) 2 ?
Br4 Br5 2.5322(6) . ?
S1 P1 1.9452(11) . ?
P1 C21 1.808(3) . ?
P1 C11 1.809(3) . ?
P1 C01 1.833(3) . ?
P2 C41 1.783(3) . ?
P2 C31 1.786(3) . ?
P2 C01 1.798(3) . ?
C11 C12 1.388(4) . ?
C11 C16 1.399(4) . ?
C12 C13 1.384(5) . ?
C13 C14 1.391(5) . ?
C14 C15 1.372(5) . ?
C15 C16 1.389(5) . ?
C21 C26 1.395(4) . ?
C21 C22 1.400(4) . ?
C22 C23 1.388(4) . ?
C23 C24 1.383(4) . ?
C24 C25 1.384(4) . ?
C25 C26 1.393(4) . ?
C31 C32 1.390(4) . ?
C31 C36 1.392(4) . ?
C32 C33 1.387(4) . ?
C33 C34 1.383(5) . ?
C34 C35 1.381(5) . ?
C35 C36 1.385(4) . ?
C41 C46 1.389(4) . ?
C41 C42 1.402(4) . ?
C42 C43 1.374(5) . ?
C43 C44 1.393(5) . ?
C44 C45 1.382(5) . ?
C45 C46 1.388(5) . ?

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
Br2 Br3 Br2 180.000(10) 7_556 . ?
Br5 Br4 Br5 178.04(3) 2 . ?
C21 P1 C11 104.93(13) . . ?
C21 P1 C01 103.10(13) . . ?
C11 P1 C01 105.59(14) . . ?
C21 P1 S1 114.03(10) . . ?
C11 P1 S1 114.13(11) . . ?
C01 P1 S1 113.95(10) . . ?
C41 P2 C31 112.35(14) . . ?
C41 P2 C01 112.96(14) . . ?
C31 P2 C01 114.63(14) . . ?
C41 P2 Br1 106.53(10) . . ?
C31 P2 Br1 105.93(11) . . ?
C01 P2 Br1 103.41(10) . . ?
P2 C01 P1 117.33(16) . . ?
C12 C11 C16 119.9(3) . . ?
C12 C11 P1 120.6(2) . . ?
C16 C11 P1 119.5(3) . . ?
C13 C12 C11 120.0(3) . . ?
C12 C13 C14 120.1(4) . . ?
C15 C14 C13 120.1(3) . . ?
C14 C15 C16 120.6(3) . . ?
C15 C16 C11 119.4(3) . . ?
C26 C21 C22 119.5(3) . . ?
C26 C21 P1 124.9(2) . . ?
C22 C21 P1 115.5(2) . . ?
C23 C22 C21 120.4(3) . . ?
C24 C23 C22 119.6(3) . . ?
C23 C24 C25 120.7(3) . . ?
C24 C25 C26 120.2(3) . . ?
C25 C26 C21 119.6(3) . . ?
C32 C31 C36 120.7(3) . . ?
C32 C31 P2 117.1(2) . . ?
C36 C31 P2 122.2(2) . . ?
C33 C32 C31 119.6(3) . . ?
C34 C33 C32 119.7(3) . . ?
C35 C34 C33 120.5(3) . . ?
C34 C35 C36 120.5(3) . . ?
C35 C36 C31 119.0(3) . . ?
C46 C41 C42 120.4(3) . . ?
C46 C41 P2 119.2(2) . . ?
C42 C41 P2 120.4(2) . . ?
C43 C42 C41 119.6(3) . . ?
C42 C43 C44 120.4(3) . . ?
C45 C44 C43 119.8(3) . . ?
C44 C45 C46 120.7(3) . . ?
C45 C46 C41 119.2(3) . . ?

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        28.70
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.833
_refine_diff_density_min         -0.600
_refine_diff_density_rms         0.101


# end of cif file
####################################################################### 
# 
# 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_leon
_database_code_depnum_ccdc_archive 'CCDC 1496346'
_audit_update_record             
;
2016-07-27 deposited with the CCDC.
2018-02-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C26 H62 Br6 O4 P4 Se2'
_chemical_formula_weight         1200.02

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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 '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'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   10.2092(4)
_cell_length_b                   13.8414(5)
_cell_length_c                   16.6253(6)
_cell_angle_alpha                81.773(4)
_cell_angle_beta                 73.151(4)
_cell_angle_gamma                73.308(4)
_cell_volume                     2149.10(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    29933
_cell_measurement_theta_min      2.5550
_cell_measurement_theta_max      30.7180

_exptl_crystal_description       plate
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.8
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.1
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.854
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1176
_exptl_absorpt_coefficient_mu    7.475
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.30588
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur, Eos'
_diffrn_measurement_method       'ω scan'
_diffrn_detector_area_resol_mean 16.1419
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            163196
_diffrn_reflns_av_R_equivalents  0.0518
_diffrn_reflns_av_sigmaI/netI    0.0289
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.16
_diffrn_reflns_theta_max         31.04
_reflns_number_total             12992
_reflns_number_gt                10719
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET)
(compiled Aug 13 2014,18:06:01)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker XP'
_computing_publication_material  SHELXL-97

_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.

 OH hydrogens were refined freely but with an OH distance restraint.

 The isopropyl group at C7 is disordered over two positions.  Appropriate
 restraints were employed, but the dimensions of disordered groups
 should always be interpreted with caution.
;

_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)+(0.0180P)²+1.5410P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         12992
_refine_ls_number_parameters     415
_refine_ls_number_restraints     20
_refine_ls_R_factor_all          0.0414
_refine_ls_R_factor_gt           0.0270
_refine_ls_wR_factor_ref         0.0518
_refine_ls_wR_factor_gt          0.0483
_refine_ls_goodness_of_fit_ref   1.046
_refine_ls_restrained_S_all      1.045
_refine_ls_shift/su_max          0.002
_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
Br1 Br 0.16308(2) 0.270294(16) 0.504312(12) 0.02157(5) Uani 1 1 d . . .
Br2 Br 0.53082(2) 0.210127(16) 0.400106(13) 0.02083(5) Uani 1 1 d . . .
Br3 Br 0.06024(2) 0.357451(15) 0.308015(12) 0.01681(4) Uani 1 1 d . . .
Br4 Br 0.45420(2) 0.276793(15) 0.187571(12) 0.01739(4) Uani 1 1 d . . .
Br5 Br 0.33195(2) 0.342654(16) -0.013600(13) 0.02033(5) Uani 1 1 d . . .
Br6 Br -0.02640(2) 0.418748(15) 0.102483(13) 0.01812(5) Uani 1 1 d . . .
Se1 Se 0.30628(2) 0.273613(14) 0.359648(12) 0.01351(4) Uani 1 1 d . . .
Se2 Se 0.20085(2) 0.352772(14) 0.132871(12) 0.01309(4) Uani 1 1 d . . .
P1 P 0.36177(5) 0.59960(4) 0.30183(3) 0.01137(9) Uani 1 1 d . . .
P2 P 0.16251(5) 0.67796(4) 0.18659(3) 0.01146(9) Uani 1 1 d . . .
P3 P 0.39488(5) 0.94821(4) 0.26053(3) 0.01232(10) Uani 1 1 d . . .
P4 P 0.09549(5) 1.03701(4) 0.23886(3) 0.01169(9) Uani 1 1 d . . .
O1 O 0.12709(15) 0.77102(10) 0.23587(8) 0.0152(3) Uani 1 1 d . . .
O2 O 0.42765(15) 0.68753(10) 0.25959(9) 0.0153(3) Uani 1 1 d D . .
H01 H 0.381(3) 0.767(2) 0.273(2) 0.064(10) Uiso 1 1 d D . .
O3 O 0.32515(15) 0.86223(10) 0.29408(9) 0.0156(3) Uani 1 1 d . . .
O4 O 0.11794(15) 0.94593(10) 0.18929(8) 0.0152(3) Uani 1 1 d D A .
H02 H 0.128(4) 0.867(2) 0.212(2) 0.101(14) Uiso 1 1 d D . .
C01 C 0.2640(2) 0.56984(14) 0.23819(13) 0.0162(4) Uani 1 1 d . . .
H01A H 0.1981 0.5312 0.2744 0.019 Uiso 1 1 calc R . .
H01B H 0.3316 0.5252 0.1944 0.019 Uiso 1 1 calc R . .
C02 C 0.2612(2) 1.06055(14) 0.24005(12) 0.0130(4) Uani 1 1 d . A .
H02A H 0.3002 1.0936 0.1849 0.016 Uiso 1 1 calc R . .
H02B H 0.2410 1.1084 0.2837 0.016 Uiso 1 1 calc R . .
C1 C 0.2362(2) 0.62916(15) 0.40268(12) 0.0162(4) Uani 1 1 d . . .
H1 H 0.1475 0.6747 0.3905 0.019 Uiso 1 1 calc R . .
C2 C 0.5067(2) 0.48941(15) 0.30533(13) 0.0167(4) Uani 1 1 d . . .
H2 H 0.4678 0.4287 0.3208 0.020 Uiso 1 1 calc R . .
C3 C 0.2751(2) 0.69093(15) 0.08113(12) 0.0160(4) Uani 1 1 d . . .
H3 H 0.3690 0.6913 0.0881 0.019 Uiso 1 1 calc R . .
C4 C 0.0025(2) 0.64426(15) 0.18936(13) 0.0168(4) Uani 1 1 d . . .
H4 H 0.0304 0.5743 0.1699 0.020 Uiso 1 1 calc R . .
C5 C 0.4707(2) 0.97487(15) 0.33746(12) 0.0166(4) Uani 1 1 d . . .
H5 H 0.5057 1.0368 0.3174 0.020 Uiso 1 1 calc R . .
C6 C 0.5302(2) 0.91909(15) 0.16265(13) 0.0176(4) Uani 1 1 d . . .
H6 H 0.5965 0.8527 0.1734 0.021 Uiso 1 1 calc R . .
C7 C 0.0055(3) 1.01694(18) 0.34874(15) 0.0156(5) Uani 0.895(4) 1 d PDU A 1
H7 H 0.0765 0.9674 0.3751 0.019 Uiso 0.895(4) 1 calc PR A 1
C71 C -0.1155(3) 0.96790(18) 0.35834(16) 0.0234(6) Uani 0.895(4) 1 d PD A 1
H71A H -0.1526 0.9486 0.4179 0.035 Uiso 0.895(4) 1 calc PR A 1
H71B H -0.0800 0.9076 0.3259 0.035 Uiso 0.895(4) 1 calc PR A 1
H71C H -0.1914 1.0161 0.3374 0.035 Uiso 0.895(4) 1 calc PR A 1
C72 C -0.0440(3) 1.1130(2) 0.39724(19) 0.0207(6) Uani 0.895(4) 1 d PDU A 1
H72A H -0.1207 1.1615 0.3772 0.031 Uiso 0.895(4) 1 calc PR A 1
H72B H 0.0355 1.1432 0.3880 0.031 Uiso 0.895(4) 1 calc PR A 1
H72C H -0.0783 1.0957 0.4575 0.031 Uiso 0.895(4) 1 calc PR A 1
C7' C -0.045(3) 1.0343(13) 0.3398(13) 0.016 Uiso 0.105(4) 1 d PDU A 2
H7' H -0.1326 1.0329 0.3255 0.019 Uiso 0.105(4) 1 calc PR A 2
C71' C -0.002(2) 0.9383(13) 0.3933(13) 0.023 Uiso 0.105(4) 1 d PD A 2
H71D H 0.0744 0.9427 0.4163 0.035 Uiso 0.105(4) 1 calc PR A 2
H71E H 0.0318 0.8802 0.3585 0.035 Uiso 0.105(4) 1 calc PR A 2
H71F H -0.0836 0.9301 0.4396 0.035 Uiso 0.105(4) 1 calc PR A 2
C72' C -0.079(3) 1.1308(16) 0.3858(19) 0.019 Uiso 0.105(4) 1 d PDU A 2
H72D H -0.1559 1.1296 0.4369 0.029 Uiso 0.105(4) 1 calc PR A 2
H72E H -0.1073 1.1901 0.3488 0.029 Uiso 0.105(4) 1 calc PR A 2
H72F H 0.0057 1.1341 0.4010 0.029 Uiso 0.105(4) 1 calc PR A 2
C8 C 0.0103(2) 1.14717(14) 0.18253(12) 0.0143(4) Uani 1 1 d . A .
H8 H 0.0183 1.2087 0.2038 0.017 Uiso 1 1 calc R . .
C11 C 0.2835(3) 0.68751(16) 0.45640(13) 0.0258(5) Uani 1 1 d . . .
H11A H 0.2101 0.7024 0.5094 0.039 Uiso 1 1 calc R . .
H11B H 0.2985 0.7509 0.4255 0.039 Uiso 1 1 calc R . .
H11C H 0.3722 0.6464 0.4685 0.039 Uiso 1 1 calc R . .
C12 C 0.1965(2) 0.53407(16) 0.45193(13) 0.0223(5) Uani 1 1 d . . .
H12A H 0.2806 0.4871 0.4655 0.033 Uiso 1 1 calc R . .
H12B H 0.1605 0.5013 0.4175 0.033 Uiso 1 1 calc R . .
H12C H 0.1232 0.5534 0.5042 0.033 Uiso 1 1 calc R . .
C21 C 0.6117(2) 0.47725(17) 0.21768(14) 0.0251(5) Uani 1 1 d . . .
H21A H 0.6542 0.5346 0.2025 0.038 Uiso 1 1 calc R . .
H21B H 0.5615 0.4750 0.1762 0.038 Uiso 1 1 calc R . .
H21C H 0.6863 0.4143 0.2185 0.038 Uiso 1 1 calc R . .
C22 C 0.5827(3) 0.49464(18) 0.37075(15) 0.0282(5) Uani 1 1 d . . .
H22A H 0.6684 0.4385 0.3651 0.042 Uiso 1 1 calc R . .
H22B H 0.5196 0.4898 0.4274 0.042 Uiso 1 1 calc R . .
H22C H 0.6088 0.5589 0.3617 0.042 Uiso 1 1 calc R . .
C31 C 0.3033(2) 0.60042(16) 0.02923(13) 0.0236(5) Uani 1 1 d . . .
H31A H 0.2144 0.5974 0.0195 0.035 Uiso 1 1 calc R . .
H31B H 0.3420 0.5379 0.0600 0.035 Uiso 1 1 calc R . .
H31C H 0.3715 0.6082 -0.0250 0.035 Uiso 1 1 calc R . .
C32 C 0.2244(2) 0.79079(16) 0.03199(13) 0.0213(4) Uani 1 1 d . . .
H32A H 0.3000 0.7995 -0.0183 0.032 Uiso 1 1 calc R . .
H32B H 0.2002 0.8471 0.0678 0.032 Uiso 1 1 calc R . .
H32C H 0.1406 0.7895 0.0151 0.032 Uiso 1 1 calc R . .
C41 C -0.0808(3) 0.71476(19) 0.13168(15) 0.0292(5) Uani 1 1 d . . .
H41A H -0.1718 0.6990 0.1408 0.044 Uiso 1 1 calc R . .
H41B H -0.0266 0.7056 0.0728 0.044 Uiso 1 1 calc R . .
H41C H -0.0975 0.7850 0.1444 0.044 Uiso 1 1 calc R . .
C42 C -0.0894(2) 0.64299(17) 0.28007(14) 0.0255(5) Uani 1 1 d . . .
H42A H -0.1210 0.7114 0.2997 0.038 Uiso 1 1 calc R . .
H42B H -0.0340 0.5976 0.3162 0.038 Uiso 1 1 calc R . .
H42C H -0.1721 0.6191 0.2824 0.038 Uiso 1 1 calc R . .
C51 C 0.5955(3) 0.88526(18) 0.34802(16) 0.0293(5) Uani 1 1 d . . .
H51A H 0.6319 0.8968 0.3933 0.044 Uiso 1 1 calc R . .
H51B H 0.6709 0.8786 0.2953 0.044 Uiso 1 1 calc R . .
H51C H 0.5636 0.8231 0.3622 0.044 Uiso 1 1 calc R . .
C52 C 0.3584(2) 0.99297(16) 0.42166(12) 0.0197(4) Uani 1 1 d . . .
H52A H 0.3270 0.9313 0.4429 0.029 Uiso 1 1 calc R . .
H52B H 0.2773 1.0483 0.4137 0.029 Uiso 1 1 calc R . .
H52C H 0.3990 1.0108 0.4624 0.029 Uiso 1 1 calc R . .
C61 C 0.6189(3) 0.99614(18) 0.13272(15) 0.0295(5) Uani 1 1 d . . .
H61A H 0.6926 0.9746 0.0811 0.044 Uiso 1 1 calc R . .
H61B H 0.6633 1.0006 0.1766 0.044 Uiso 1 1 calc R . .
H61C H 0.5576 1.0625 0.1213 0.044 Uiso 1 1 calc R . .
C62 C 0.4643(2) 0.90462(17) 0.09487(13) 0.0237(5) Uani 1 1 d . . .
H62A H 0.4027 0.9693 0.0801 0.036 Uiso 1 1 calc R . .
H62B H 0.4084 0.8551 0.1164 0.036 Uiso 1 1 calc R . .
H62C H 0.5396 0.8802 0.0447 0.036 Uiso 1 1 calc R . .
C81 C -0.1468(2) 1.15593(17) 0.19364(15) 0.0253(5) Uani 1 1 d . . .
H81A H -0.1859 1.2147 0.1592 0.038 Uiso 1 1 calc R A .
H81B H -0.1982 1.1642 0.2530 0.038 Uiso 1 1 calc R . .
H81C H -0.1569 1.0945 0.1758 0.038 Uiso 1 1 calc R . .
C82 C 0.0908(2) 1.14259(15) 0.08883(12) 0.0186(4) Uani 1 1 d . . .
H82A H 0.0812 1.0840 0.0664 0.028 Uiso 1 1 calc R A .
H82B H 0.1912 1.1364 0.0826 0.028 Uiso 1 1 calc R . .
H82C H 0.0512 1.2045 0.0577 0.028 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
Br1 Se1 2.4275(3) . ?
Br2 Se1 2.4590(3) . ?
Br3 Se1 2.7719(3) . ?
Br3 Se2 2.8497(3) . ?
Br4 Se1 2.8221(3) . ?
Br4 Se2 2.8549(3) . ?
Br5 Se2 2.4169(3) . ?
Br6 Se2 2.4087(3) . ?
P1 O2 1.5422(14) . ?
P1 C2 1.802(2) . ?
P1 C01 1.805(2) . ?
P1 C1 1.809(2) . ?
P2 O1 1.5244(14) . ?
P2 C4 1.810(2) . ?
P2 C3 1.813(2) . ?
P2 C01 1.818(2) . ?
P3 O3 1.5168(14) . ?
P3 C5 1.801(2) . ?
P3 C6 1.812(2) . ?
P3 C02 1.8155(19) . ?
P4 O4 1.5307(14) . ?
P4 C8 1.8057(19) . ?
P4 C7 1.813(2) . ?
P4 C02 1.818(2) . ?
P4 C7' 1.87(2) . ?
C1 C11 1.538(3) . ?
C1 C12 1.540(3) . ?
C2 C22 1.528(3) . ?
C2 C21 1.537(3) . ?
C3 C31 1.534(3) . ?
C3 C32 1.535(3) . ?
C4 C41 1.524(3) . ?
C4 C42 1.529(3) . ?
C5 C52 1.530(3) . ?
C5 C51 1.534(3) . ?
C6 C62 1.531(3) . ?
C6 C61 1.532(3) . ?
C7 C71 1.533(3) . ?
C7 C72 1.536(3) . ?
C7' C71' 1.517(15) . ?
C7' C72' 1.536(15) . ?
C8 C81 1.531(3) . ?
C8 C82 1.537(3) . ?

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
Se1 Br3 Se2 94.582(9) . . ?
Se1 Br4 Se2 93.386(9) . . ?
Br1 Se1 Br2 93.346(10) . . ?
Br1 Se1 Br3 88.994(10) . . ?
Br2 Se1 Br3 175.759(10) . . ?
Br1 Se1 Br4 175.526(11) . . ?
Br2 Se1 Br4 90.792(10) . . ?
Br3 Se1 Br4 86.982(9) . . ?
Br6 Se2 Br5 94.186(11) . . ?
Br6 Se2 Br3 88.942(9) . . ?
Br5 Se2 Br3 176.756(11) . . ?
Br6 Se2 Br4 173.827(10) . . ?
Br5 Se2 Br4 91.980(10) . . ?
Br3 Se2 Br4 84.898(9) . . ?
O2 P1 C2 106.86(9) . . ?
O2 P1 C01 111.15(9) . . ?
C2 P1 C01 105.90(10) . . ?
O2 P1 C1 112.61(8) . . ?
C2 P1 C1 114.53(9) . . ?
C01 P1 C1 105.65(10) . . ?
O1 P2 C4 110.52(9) . . ?
O1 P2 C3 112.54(8) . . ?
C4 P2 C3 113.65(10) . . ?
O1 P2 C01 109.43(8) . . ?
C4 P2 C01 104.98(9) . . ?
C3 P2 C01 105.23(10) . . ?
O3 P3 C5 110.21(9) . . ?
O3 P3 C6 111.28(9) . . ?
C5 P3 C6 110.01(10) . . ?
O3 P3 C02 108.82(9) . . ?
C5 P3 C02 108.41(9) . . ?
C6 P3 C02 108.04(9) . . ?
O4 P4 C8 106.81(9) . . ?
O4 P4 C7 111.29(9) . . ?
C8 P4 C7 116.17(11) . . ?
O4 P4 C02 112.72(9) . . ?
C8 P4 C02 104.78(9) . . ?
C7 P4 C02 105.03(11) . . ?
O4 P4 C7' 110.3(6) . . ?
C8 P4 C7' 101.4(6) . . ?
C7 P4 C7' 17.2(6) . . ?
C02 P4 C7' 119.3(7) . . ?
P1 C01 P2 115.42(10) . . ?
P3 C02 P4 114.48(10) . . ?
C11 C1 C12 111.50(17) . . ?
C11 C1 P1 113.66(15) . . ?
C12 C1 P1 111.52(14) . . ?
C22 C2 C21 110.22(18) . . ?
C22 C2 P1 112.07(15) . . ?
C21 C2 P1 109.55(14) . . ?
C31 C3 C32 110.85(17) . . ?
C31 C3 P2 112.82(14) . . ?
C32 C3 P2 114.14(14) . . ?
C41 C4 C42 110.65(18) . . ?
C41 C4 P2 112.59(15) . . ?
C42 C4 P2 109.36(15) . . ?
C52 C5 C51 110.16(17) . . ?
C52 C5 P3 109.93(14) . . ?
C51 C5 P3 109.16(15) . . ?
C62 C6 C61 111.95(18) . . ?
C62 C6 P3 110.25(15) . . ?
C61 C6 P3 113.42(15) . . ?
C71 C7 C72 112.0(2) . . ?
C71 C7 P4 111.36(17) . . ?
C72 C7 P4 113.06(18) . . ?
C71' C7' C72' 113.1(17) . . ?
C71' C7' P4 110.2(15) . . ?
C72' C7' P4 110.7(18) . . ?
C81 C8 C82 110.29(17) . . ?
C81 C8 P4 113.16(14) . . ?
C82 C8 P4 108.08(13) . . ?

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
O2 H01 O3 1.09(3) 1.34(3) 2.4220(19) 177(3) .
O4 H02 O1 1.09(3) 1.34(3) 2.4176(18) 173(4) .

_diffrn_measured_fraction_theta_max 0.945
_diffrn_reflns_theta_full        30.00
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.733
_refine_diff_density_min         -0.643
_refine_diff_density_rms         0.107


# start Validation Reply Form
_vrf_PLAT431_leon                
;
PROBLEM: Short Inter HL..A  Contact Br3    ..  Se2     ..       2.85 Ang.
RESPONSE: It is tolerably certain that these contacts are long but
genuine bonds.
;
# end Validation Reply Form

# end of cif file
####################################################################### 
# 
# 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_ieuan
_database_code_depnum_ccdc_archive 'CCDC 1581380'
_audit_update_record             
;
2017-10-23 deposited with the CCDC.
2018-02-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C13 H30 Br4 P2 Se2'
_chemical_formula_weight         725.87

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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   8.6805(5)
_cell_length_b                   8.9116(5)
_cell_length_c                   16.6930(8)
_cell_angle_alpha                100.220(5)
_cell_angle_beta                 90.630(4)
_cell_angle_gamma                116.279(6)
_cell_volume                     1133.61(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    103(2)
_cell_measurement_reflns_used    13193
_cell_measurement_theta_min      2.6130
_cell_measurement_theta_max      30.6300

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.127
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             692
_exptl_absorpt_coefficient_mu    10.446
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.31385
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      103(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur, Eos'
_diffrn_measurement_method       ω-scan
_diffrn_detector_area_resol_mean 16.1419
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            60914
_diffrn_reflns_av_R_equivalents  0.0480
_diffrn_reflns_av_sigmaI/netI    0.0308
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.49
_diffrn_reflns_theta_max         31.02
_reflns_number_total             6750
_reflns_number_gt                5684
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker XP'
_computing_publication_material  SHELXL-97

_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)+(0.0251P)²+0.7499P] 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_number_reflns         6750
_refine_ls_number_parameters     198
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0401
_refine_ls_R_factor_gt           0.0277
_refine_ls_wR_factor_ref         0.0574
_refine_ls_wR_factor_gt          0.0540
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_refine_ls_shift/su_max          0.002
_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
P1 P 0.74476(8) 0.64316(7) 0.33871(4) 0.01163(12) Uani 1 1 d . . .
P2 P 0.64970(8) 0.31706(7) 0.20120(4) 0.01096(11) Uani 1 1 d . . .
Se1 Se 0.80475(3) 0.47855(3) 0.408575(14) 0.01436(6) Uani 1 1 d . . .
Se2 Se 0.59325(3) 0.20842(3) 0.310559(15) 0.01600(6) Uani 1 1 d . . .
Br1 Br 1.01183(4) 0.74666(3) 0.525004(15) 0.02248(6) Uani 1 1 d . . .
C01 C 0.6956(3) 0.5413(3) 0.22998(13) 0.0121(4) Uani 1 1 d . . .
H01A H 0.5947 0.5518 0.2087 0.014 Uiso 1 1 calc R . .
H01B H 0.7946 0.6079 0.2012 0.014 Uiso 1 1 calc R . .
C1 C 0.9314(3) 0.8519(3) 0.34581(14) 0.0134(5) Uani 1 1 d . . .
H1 H 0.9484 0.9170 0.4032 0.016 Uiso 1 1 calc R . .
C2 C 0.5608(3) 0.6773(3) 0.37196(15) 0.0161(5) Uani 1 1 d . . .
H2 H 0.5362 0.7391 0.3330 0.019 Uiso 1 1 calc R . .
C3 C 0.8367(3) 0.3099(3) 0.15578(15) 0.0145(5) Uani 1 1 d . . .
H3 H 0.8666 0.3823 0.1135 0.017 Uiso 1 1 calc R . .
C4 C 0.4638(3) 0.2052(3) 0.12482(14) 0.0152(5) Uani 1 1 d . . .
H4 H 0.4454 0.0846 0.1081 0.018 Uiso 1 1 calc R . .
C11 C 0.8922(4) 0.9521(3) 0.28901(15) 0.0196(5) Uani 1 1 d . . .
H11A H 0.9863 1.0687 0.2979 0.029 Uiso 1 1 calc R . .
H11B H 0.7837 0.9561 0.3011 0.029 Uiso 1 1 calc R . .
H11C H 0.8815 0.8951 0.2319 0.029 Uiso 1 1 calc R . .
C12 C 1.0997(3) 0.8419(3) 0.32805(16) 0.0193(5) Uani 1 1 d . . .
H12A H 1.0915 0.7892 0.2704 0.029 Uiso 1 1 calc R . .
H12B H 1.1189 0.7727 0.3628 0.029 Uiso 1 1 calc R . .
H12C H 1.1963 0.9573 0.3396 0.029 Uiso 1 1 calc R . .
C21 C 0.6045(4) 0.7928(3) 0.45724(16) 0.0242(6) Uani 1 1 d . . .
H21A H 0.5027 0.8061 0.4741 0.036 Uiso 1 1 calc R . .
H21B H 0.6993 0.9052 0.4557 0.036 Uiso 1 1 calc R . .
H21C H 0.6395 0.7411 0.4965 0.036 Uiso 1 1 calc R . .
C22 C 0.3975(3) 0.5102(3) 0.36820(17) 0.0232(6) Uani 1 1 d . . .
H22A H 0.4160 0.4467 0.4065 0.035 Uiso 1 1 calc R . .
H22B H 0.3704 0.4413 0.3125 0.035 Uiso 1 1 calc R . .
H22C H 0.3012 0.5351 0.3832 0.035 Uiso 1 1 calc R . .
C31 C 0.9928(3) 0.3844(3) 0.21924(17) 0.0201(5) Uani 1 1 d . . .
H31A H 0.9720 0.3089 0.2583 0.030 Uiso 1 1 calc R . .
H31B H 1.0117 0.4977 0.2484 0.030 Uiso 1 1 calc R . .
H31C H 1.0952 0.3945 0.1918 0.030 Uiso 1 1 calc R . .
C32 C 0.7930(3) 0.1272(3) 0.11245(17) 0.0198(5) Uani 1 1 d . . .
H32A H 0.8967 0.1243 0.0914 0.030 Uiso 1 1 calc R . .
H32B H 0.7034 0.0897 0.0669 0.030 Uiso 1 1 calc R . .
H32C H 0.7508 0.0507 0.1513 0.030 Uiso 1 1 calc R . .
C41 C 0.2977(3) 0.1996(3) 0.15698(16) 0.0206(5) Uani 1 1 d . . .
H41A H 0.3069 0.3152 0.1682 0.031 Uiso 1 1 calc R . .
H41B H 0.2799 0.1551 0.2075 0.031 Uiso 1 1 calc R . .
H41C H 0.1998 0.1250 0.1159 0.031 Uiso 1 1 calc R . .
C42 C 0.5018(3) 0.2848(3) 0.04848(15) 0.0210(5) Uani 1 1 d . . .
H42A H 0.4046 0.2184 0.0061 0.031 Uiso 1 1 calc R . .
H42B H 0.6069 0.2841 0.0280 0.031 Uiso 1 1 calc R . .
H42C H 0.5183 0.4029 0.0627 0.031 Uiso 1 1 calc R . .
Br2 Br 0.42495(3) 0.73326(4) 0.170721(17) 0.02316(6) Uani 1 1 d . . .
Br3 Br 0.15178(3) 0.72646(3) 0.101450(14) 0.01537(6) Uani 1 1 d . . .
Br4 Br -0.11429(3) 0.72439(4) 0.043868(17) 0.02377(6) Uani 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
P1 C2 1.828(2) . ?
P1 C1 1.830(2) . ?
P1 C01 1.832(2) . ?
P1 Se1 2.2480(6) . ?
P2 C4 1.817(2) . ?
P2 C3 1.821(2) . ?
P2 C01 1.826(2) . ?
P2 Se2 2.1765(7) . ?
Se1 Se2 2.5427(4) . ?
Se1 Br1 2.6813(4) . ?
C1 C12 1.532(3) . ?
C1 C11 1.541(3) . ?
C2 C22 1.526(4) . ?
C2 C21 1.534(3) . ?
C3 C31 1.524(3) . ?
C3 C32 1.532(3) . ?
C4 C41 1.527(3) . ?
C4 C42 1.536(4) . ?
Br2 Br3 2.5983(4) . ?
Br3 Br4 2.4832(4) . ?

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
C2 P1 C1 108.39(11) . . ?
C2 P1 C01 107.89(11) . . ?
C1 P1 C01 106.32(11) . . ?
C2 P1 Se1 113.52(8) . . ?
C1 P1 Se1 111.38(8) . . ?
C01 P1 Se1 109.04(7) . . ?
C4 P2 C3 108.65(11) . . ?
C4 P2 C01 109.22(11) . . ?
C3 P2 C01 107.52(11) . . ?
C4 P2 Se2 109.97(8) . . ?
C3 P2 Se2 113.53(8) . . ?
C01 P2 Se2 107.86(8) . . ?
P1 Se1 Se2 91.353(18) . . ?
P1 Se1 Br1 92.773(18) . . ?
Se2 Se1 Br1 173.842(13) . . ?
P2 Se2 Se1 95.592(19) . . ?
P2 C01 P1 118.34(12) . . ?
C12 C1 C11 110.9(2) . . ?
C12 C1 P1 113.75(16) . . ?
C11 C1 P1 109.66(17) . . ?
C22 C2 C21 111.4(2) . . ?
C22 C2 P1 112.57(17) . . ?
C21 C2 P1 111.31(18) . . ?
C31 C3 C32 111.8(2) . . ?
C31 C3 P2 111.33(17) . . ?
C32 C3 P2 110.52(17) . . ?
C41 C4 C42 110.9(2) . . ?
C41 C4 P2 113.19(17) . . ?
C42 C4 P2 110.01(17) . . ?
Br4 Br3 Br2 176.439(13) . . ?

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
C2 P1 Se1 Se2 87.47(9) . . . . ?
C1 P1 Se1 Se2 -149.85(8) . . . . ?
C01 P1 Se1 Se2 -32.83(9) . . . . ?
C2 P1 Se1 Br1 -87.95(9) . . . . ?
C1 P1 Se1 Br1 34.72(8) . . . . ?
C01 P1 Se1 Br1 151.74(8) . . . . ?
C4 P2 Se2 Se1 -153.71(8) . . . . ?
C3 P2 Se2 Se1 84.34(9) . . . . ?
C01 P2 Se2 Se1 -34.69(8) . . . . ?
P1 Se1 Se2 P2 37.12(2) . . . . ?
Br1 Se1 Se2 P2 169.18(12) . . . . ?
C4 P2 C01 P1 135.87(14) . . . . ?
C3 P2 C01 P1 -106.41(15) . . . . ?
Se2 P2 C01 P1 16.37(16) . . . . ?
C2 P1 C01 P2 -108.67(15) . . . . ?
C1 P1 C01 P2 135.23(14) . . . . ?
Se1 P1 C01 P2 15.04(16) . . . . ?
C2 P1 C1 C12 174.04(17) . . . . ?
C01 P1 C1 C12 -70.20(19) . . . . ?
Se1 P1 C1 C12 48.47(18) . . . . ?
C2 P1 C1 C11 -61.17(19) . . . . ?
C01 P1 C1 C11 54.59(19) . . . . ?
Se1 P1 C1 C11 173.26(14) . . . . ?
C1 P1 C2 C22 179.91(18) . . . . ?
C01 P1 C2 C22 65.2(2) . . . . ?
Se1 P1 C2 C22 -55.8(2) . . . . ?
C1 P1 C2 C21 -54.2(2) . . . . ?
C01 P1 C2 C21 -168.92(18) . . . . ?
Se1 P1 C2 C21 70.12(19) . . . . ?
C4 P2 C3 C31 -173.77(17) . . . . ?
C01 P2 C3 C31 68.13(19) . . . . ?
Se2 P2 C3 C31 -51.09(18) . . . . ?
C4 P2 C3 C32 -48.9(2) . . . . ?
C01 P2 C3 C32 -166.99(17) . . . . ?
Se2 P2 C3 C32 73.79(18) . . . . ?
C3 P2 C4 C41 178.67(18) . . . . ?
C01 P2 C4 C41 -64.3(2) . . . . ?
Se2 P2 C4 C41 53.86(19) . . . . ?
C3 P2 C4 C42 -56.66(19) . . . . ?
C01 P2 C4 C42 60.35(19) . . . . ?
Se2 P2 C4 C42 178.53(14) . . . . ?

_diffrn_measured_fraction_theta_max 0.932
_diffrn_reflns_theta_full        30.50
_diffrn_measured_fraction_theta_full 0.963
_refine_diff_density_max         0.908
_refine_diff_density_min         -0.699
_refine_diff_density_rms         0.122


# end of cif file
####################################################################### 
# 
# 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_jenny
_database_code_depnum_ccdc_archive 'CCDC 1574228'
_audit_update_record             
;
2017-09-13 deposited with the CCDC.
2018-02-02 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C14 H32 Br6 P2 Se'
_chemical_formula_weight         820.76

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'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Se Se -0.0929 2.2259 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.8144(3)
_cell_length_b                   8.7133(5)
_cell_length_c                   9.9430(7)
_cell_angle_alpha                108.707(6)
_cell_angle_beta                 93.299(4)
_cell_angle_gamma                102.917(5)
_cell_volume                     618.86(6)
_cell_formula_units_Z            1
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    8087
_cell_measurement_theta_min      2.6980
_cell_measurement_theta_max      29.1560

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.202
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             390
_exptl_absorpt_coefficient_mu    11.329
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.34502
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Oxford Diffraction Xcalibur, Eos'
_diffrn_measurement_method       ω-scan
_diffrn_detector_area_resol_mean 16.1419
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            27190
_diffrn_reflns_av_R_equivalents  0.0428
_diffrn_reflns_av_sigmaI/netI    0.0284
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.18
_diffrn_reflns_theta_max         29.50
_reflns_number_total             3161
_reflns_number_gt                2813
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Siemens XP'
_computing_publication_material  SHELXL-97

_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)+(0.0169P)²+0.8383P] 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_number_reflns         3161
_refine_ls_number_parameters     110
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0322
_refine_ls_R_factor_gt           0.0251
_refine_ls_wR_factor_ref         0.0499
_refine_ls_wR_factor_gt          0.0475
_refine_ls_goodness_of_fit_ref   1.063
_refine_ls_restrained_S_all      1.063
_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
Se1 Se 0.0000 0.5000 0.5000 0.01037(8) Uani 1 2 d S . .
Br2 Br -0.16863(4) 0.37852(4) 0.24004(3) 0.02080(7) Uani 1 1 d . . .
Br3 Br 0.04856(4) 0.20979(3) 0.47798(3) 0.01695(7) Uani 1 1 d . . .
P1 P 0.59522(9) 0.17289(8) 0.72662(7) 0.00974(13) Uani 1 1 d . . .
Br1 Br 0.33019(3) 0.14707(3) 0.77890(3) 0.01625(7) Uani 1 1 d . . .
C1 C 0.5878(3) 0.0227(3) 0.5495(3) 0.0128(5) Uani 1 1 d . . .
H1A H 0.6855 0.0691 0.5032 0.015 Uiso 1 1 calc R . .
H1B H 0.6088 -0.0811 0.5600 0.015 Uiso 1 1 calc R . .
C2 C 0.7225(4) 0.1273(3) 0.8608(3) 0.0143(5) Uani 1 1 d . . .
H2 H 0.7044 0.1994 0.9570 0.017 Uiso 1 1 calc R . .
C3 C 0.6575(4) -0.0551(4) 0.8519(3) 0.0228(6) Uani 1 1 d . . .
H3A H 0.6921 -0.1283 0.7663 0.034 Uiso 1 1 calc R . .
H3B H 0.5281 -0.0848 0.8463 0.034 Uiso 1 1 calc R . .
H3C H 0.7106 -0.0691 0.9375 0.034 Uiso 1 1 calc R . .
C4 C 0.9199(4) 0.1749(4) 0.8499(3) 0.0196(6) Uani 1 1 d . . .
H4A H 0.9868 0.1501 0.9232 0.029 Uiso 1 1 calc R . .
H4B H 0.9583 0.2949 0.8647 0.029 Uiso 1 1 calc R . .
H4C H 0.9413 0.1103 0.7546 0.029 Uiso 1 1 calc R . .
C5 C 0.6815(4) 0.3830(3) 0.7282(3) 0.0131(5) Uani 1 1 d . . .
H5 H 0.8058 0.3925 0.7058 0.016 Uiso 1 1 calc R . .
C6 C 0.6904(4) 0.5133(3) 0.8760(3) 0.0213(6) Uani 1 1 d . . .
H6A H 0.7618 0.6225 0.8789 0.032 Uiso 1 1 calc R . .
H6B H 0.7448 0.4795 0.9495 0.032 Uiso 1 1 calc R . .
H6C H 0.5703 0.5215 0.8943 0.032 Uiso 1 1 calc R . .
C7 C 0.5770(4) 0.4187(4) 0.6112(3) 0.0177(6) Uani 1 1 d . . .
H7A H 0.4523 0.4033 0.6262 0.026 Uiso 1 1 calc R . .
H7B H 0.5855 0.3414 0.5169 0.026 Uiso 1 1 calc R . .
H7C H 0.6264 0.5344 0.6159 0.026 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
Se1 Br3 2.5826(3) 2_566 ?
Se1 Br3 2.5826(3) . ?
Se1 Br2 2.6014(3) . ?
Se1 Br2 2.6015(3) 2_566 ?
P1 C5 1.799(3) . ?
P1 C2 1.814(3) . ?
P1 C1 1.815(3) . ?
P1 Br1 2.1450(7) . ?
C1 C1 1.537(5) 2_656 ?
C2 C4 1.525(4) . ?
C2 C3 1.528(4) . ?
C5 C6 1.529(4) . ?
C5 C7 1.534(4) . ?

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
Br3 Se1 Br3 180.0 2_566 . ?
Br3 Se1 Br2 89.628(11) 2_566 . ?
Br3 Se1 Br2 90.371(11) . . ?
Br3 Se1 Br2 90.372(11) 2_566 2_566 ?
Br3 Se1 Br2 89.629(11) . 2_566 ?
Br2 Se1 Br2 180.000(13) . 2_566 ?
C5 P1 C2 111.91(13) . . ?
C5 P1 C1 110.29(12) . . ?
C2 P1 C1 110.64(12) . . ?
C5 P1 Br1 108.77(9) . . ?
C2 P1 Br1 106.72(9) . . ?
C1 P1 Br1 108.38(9) . . ?
C1 C1 P1 114.2(2) 2_656 . ?
C4 C2 C3 112.1(2) . . ?
C4 C2 P1 110.44(19) . . ?
C3 C2 P1 111.80(19) . . ?
C6 C5 C7 111.5(2) . . ?
C6 C5 P1 111.85(18) . . ?
C7 C5 P1 111.62(19) . . ?

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 P1 C1 C1 -90.7(3) . . . 2_656 ?
C2 P1 C1 C1 144.9(3) . . . 2_656 ?
Br1 P1 C1 C1 28.2(3) . . . 2_656 ?
C5 P1 C2 C4 -50.2(2) . . . . ?
C1 P1 C2 C4 73.2(2) . . . . ?
Br1 P1 C2 C4 -169.09(17) . . . . ?
C5 P1 C2 C3 -175.78(19) . . . . ?
C1 P1 C2 C3 -52.4(2) . . . . ?
Br1 P1 C2 C3 65.3(2) . . . . ?
C2 P1 C5 C6 -56.2(2) . . . . ?
C1 P1 C5 C6 -179.80(19) . . . . ?
Br1 P1 C5 C6 61.5(2) . . . . ?
C2 P1 C5 C7 178.13(18) . . . . ?
C1 P1 C5 C7 54.5(2) . . . . ?
Br1 P1 C5 C7 -64.22(19) . . . . ?

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
C1 H1A Br3 0.99 2.89 3.813(3) 156.0 1_655
C1 H1A Br1 0.99 2.81 3.290(3) 110.5 2_656
C2 H2 Br2 1.00 2.74 3.639(3) 149.7 1_656
C5 H5 Se1 1.00 2.88 3.658(3) 134.7 1_655
C5 H5 Br2 1.00 2.99 3.849(3) 145.1 2_666

_diffrn_measured_fraction_theta_max 0.918
_diffrn_reflns_theta_full        28.00
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.739
_refine_diff_density_min         -0.618
_refine_diff_density_rms         0.123

