# Electronic Supplementary Material (ESI) for ChemComm.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_ortho_2mdppo_14tfib_123K
_database_code_depnum_ccdc_archive 'CCDC 1831924'
loop_
_audit_author_name
_audit_author_address
'Filip Topic'
;McGill University
Canada
;
_audit_update_record             
;
2018-03-23 deposited with the CCDC.	2019-10-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_formula_moiety         '2(C13 H13 O P), C6 F4 I2'
_chemical_formula_sum            'C32 H26 F4 I2 O2 P2'
_chemical_formula_weight         834.27

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'
F F 0.0171 0.0103 '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'
O O 0.0106 0.0060 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   5.72260(10)
_cell_length_b                   16.3731(3)
_cell_length_c                   32.1528(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3012.61(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    123.0(1)
_cell_measurement_reflns_used    3900
_cell_measurement_theta_min      0.407
_cell_measurement_theta_max      27.485

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.839
_exptl_crystal_F_000             1624
_exptl_crystal_size_max          0.230
_exptl_crystal_size_mid          0.180
_exptl_crystal_size_min          0.140
_exptl_absorpt_coefficient_mu    2.249
_shelx_estimated_absorpt_T_min   0.626
_shelx_estimated_absorpt_T_max   0.744
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5553
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   'SADABS 2008 (Sheldrick, 1996)'
_exptl_absorpt_special_details   ?

_diffrn_ambient_temperature      123.0(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_method       'φ scans + ω scans'
_diffrn_detector_area_resol_mean 9
_diffrn_reflns_number            15206
_diffrn_reflns_av_unetI/netI     0.0377
_diffrn_reflns_av_R_equivalents  0.0389
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_limit_l_max       42
_diffrn_reflns_theta_min         2.567
_diffrn_reflns_theta_max         27.987
_diffrn_reflns_theta_full        25.250
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measured_fraction_theta_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_point_group_measured_fraction_full 0.986
_reflns_number_total             3579
_reflns_number_gt                3352
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor, 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2015)'
_computing_publication_material  
'OLEX2 (Dolomanov et al., 2009) & WinGX publication routines (Farrugia, 2012)'

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+13.4079P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_extinction_coef       0.0015(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3579
_refine_ls_number_parameters     192
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0448
_refine_ls_R_factor_gt           0.0419
_refine_ls_wR_factor_ref         0.1069
_refine_ls_wR_factor_gt          0.1058
_refine_ls_goodness_of_fit_ref   1.306
_refine_ls_restrained_S_all      1.306
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1A C 0.4172(7) 0.7388(2) 0.12549(12) 0.0203(8) Uani 1 1 d . . . . .
C2A C 0.2601(8) 0.7809(3) 0.10103(14) 0.0247(8) Uani 1 1 d . . . . .
H2A H 0.114973 0.798266 0.112328 0.030 Uiso 1 1 calc R U . . .
C3A C 0.3153(8) 0.7982(3) 0.05941(14) 0.0273(9) Uani 1 1 d . . . . .
H3A H 0.209069 0.828339 0.042680 0.033 Uiso 1 1 calc R U . . .
C4A C 0.5240(8) 0.7713(3) 0.04279(13) 0.0267(9) Uani 1 1 d . . . . .
H4A H 0.558898 0.781785 0.014407 0.032 Uiso 1 1 calc R U . . .
C5A C 0.6830(8) 0.7290(3) 0.06719(14) 0.0275(9) Uani 1 1 d . . . . .
H5A H 0.826710 0.710912 0.055639 0.033 Uiso 1 1 calc R U . . .
C6A C 0.6308(8) 0.7133(3) 0.10874(13) 0.0244(9) Uani 1 1 d . . . . .
H6A H 0.740371 0.685296 0.125733 0.029 Uiso 1 1 calc R U . . .
C7A C 0.4065(7) 0.6087(3) 0.18555(12) 0.0207(8) Uani 1 1 d . . . . .
C8A C 0.6086(8) 0.5804(3) 0.20510(13) 0.0257(9) Uani 1 1 d . . . . .
H8A H 0.719094 0.618216 0.215907 0.031 Uiso 1 1 calc R U . . .
C9A C 0.6485(8) 0.4964(3) 0.20879(14) 0.0268(9) Uani 1 1 d . . . . .
H9A H 0.785387 0.477181 0.222346 0.032 Uiso 1 1 calc R U . . .
C10A C 0.4888(8) 0.4412(3) 0.19270(13) 0.0279(9) Uani 1 1 d . . . . .
H10A H 0.516940 0.384247 0.195284 0.033 Uiso 1 1 calc R U . . .
C11A C 0.2883(8) 0.4684(3) 0.17286(14) 0.0254(9) Uani 1 1 d . . . . .
H11A H 0.180188 0.430435 0.161525 0.031 Uiso 1 1 calc R U . . .
C12A C 0.2465(8) 0.5524(3) 0.16967(13) 0.0233(8) Uani 1 1 d . . . . .
H12A H 0.107845 0.571252 0.156570 0.028 Uiso 1 1 calc R U . . .
C13A C 0.5346(8) 0.7714(3) 0.21092(13) 0.0239(8) Uani 1 1 d . . . . .
H13A H 0.497282 0.829703 0.209330 0.036 Uiso 1 1 calc R U . . .
H13B H 0.695107 0.762424 0.201337 0.036 Uiso 1 1 calc R U . . .
H13C H 0.519504 0.752746 0.239759 0.036 Uiso 1 1 calc R U . . .
O1A O 0.0848(5) 0.73268(19) 0.18630(9) 0.0240(6) Uani 1 1 d . . . . .
P1A P 0.33734(18) 0.71529(6) 0.17870(3) 0.0187(2) Uani 1 1 d . . . . .
C1B C 0.8728(8) 0.4907(3) 0.03707(13) 0.0222(8) Uani 1 1 d . . . . .
C2B C 0.8021(7) 0.4532(3) 0.00068(14) 0.0226(8) Uani 1 1 d . . . . .
C3B C 0.9282(8) 0.4614(2) -0.03552(13) 0.0225(8) Uani 1 1 d . . . . .
F1B F 0.6070(5) 0.40729(17) 0.00012(8) 0.0312(6) Uani 1 1 d . . . . .
F2B F 0.8531(5) 0.42218(17) -0.06986(8) 0.0301(6) Uani 1 1 d . . . . .
I1B I 0.68972(5) 0.47469(2) 0.09239(2) 0.02887(14) 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
C1A C2A 1.379(6) . ?
C1A C6A 1.399(6) . ?
C1A P1A 1.812(4) . ?
C2A C3A 1.404(6) . ?
C2A H2A 0.9500 . ?
C3A C4A 1.380(7) . ?
C3A H3A 0.9500 . ?
C4A C5A 1.386(6) . ?
C4A H4A 0.9500 . ?
C5A C6A 1.393(6) . ?
C5A H5A 0.9500 . ?
C6A H6A 0.9500 . ?
C7A C8A 1.396(6) . ?
C7A C12A 1.396(6) . ?
C7A P1A 1.803(4) . ?
C8A C9A 1.400(6) . ?
C8A H8A 0.9500 . ?
C9A C10A 1.385(7) . ?
C9A H9A 0.9500 . ?
C10A C11A 1.387(7) . ?
C10A H10A 0.9500 . ?
C11A C12A 1.398(6) . ?
C11A H11A 0.9500 . ?
C12A H12A 0.9500 . ?
C13A P1A 1.786(4) . ?
C13A H13A 0.9800 . ?
C13A H13B 0.9800 . ?
C13A H13C 0.9800 . ?
O1A P1A 1.493(3) . ?
C1B C2B 1.382(6) . ?
C1B C3B 1.383(6) 5_765 ?
C1B I1B 2.081(4) . ?
C2B F1B 1.347(5) . ?
C2B C3B 1.376(6) . ?
C3B F2B 1.348(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
C2A C1A C6A 119.9(4) . . ?
C2A C1A P1A 118.7(3) . . ?
C6A C1A P1A 121.4(3) . . ?
C1A C2A C3A 119.9(4) . . ?
C1A C2A H2A 120.1 . . ?
C3A C2A H2A 120.1 . . ?
C4A C3A C2A 120.0(4) . . ?
C4A C3A H3A 120.0 . . ?
C2A C3A H3A 120.0 . . ?
C3A C4A C5A 120.5(4) . . ?
C3A C4A H4A 119.7 . . ?
C5A C4A H4A 119.7 . . ?
C4A C5A C6A 119.6(4) . . ?
C4A C5A H5A 120.2 . . ?
C6A C5A H5A 120.2 . . ?
C5A C6A C1A 120.1(4) . . ?
C5A C6A H6A 119.9 . . ?
C1A C6A H6A 119.9 . . ?
C8A C7A C12A 119.3(4) . . ?
C8A C7A P1A 123.9(3) . . ?
C12A C7A P1A 116.8(3) . . ?
C7A C8A C9A 119.9(4) . . ?
C7A C8A H8A 120.0 . . ?
C9A C8A H8A 120.0 . . ?
C10A C9A C8A 120.1(4) . . ?
C10A C9A H9A 119.9 . . ?
C8A C9A H9A 119.9 . . ?
C9A C10A C11A 120.5(4) . . ?
C9A C10A H10A 119.7 . . ?
C11A C10A H10A 119.7 . . ?
C10A C11A C12A 119.4(4) . . ?
C10A C11A H11A 120.3 . . ?
C12A C11A H11A 120.3 . . ?
C7A C12A C11A 120.7(4) . . ?
C7A C12A H12A 119.7 . . ?
C11A C12A H12A 119.7 . . ?
P1A C13A H13A 109.5 . . ?
P1A C13A H13B 109.5 . . ?
H13A C13A H13B 109.5 . . ?
P1A C13A H13C 109.5 . . ?
H13A C13A H13C 109.5 . . ?
H13B C13A H13C 109.5 . . ?
O1A P1A C13A 114.75(19) . . ?
O1A P1A C7A 112.15(19) . . ?
C13A P1A C7A 106.7(2) . . ?
O1A P1A C1A 110.98(18) . . ?
C13A P1A C1A 106.21(19) . . ?
C7A P1A C1A 105.40(18) . . ?
C2B C1B C3B 117.5(4) . 5_765 ?
C2B C1B I1B 121.4(3) . . ?
C3B C1B I1B 121.1(3) 5_765 . ?
F1B C2B C3B 118.6(4) . . ?
F1B C2B C1B 120.1(4) . . ?
C3B C2B C1B 121.3(4) . . ?
F2B C3B C2B 118.6(4) . . ?
F2B C3B C1B 120.2(4) . 5_765 ?
C2B C3B C1B 121.1(4) . 5_765 ?

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
C6A C1A C2A C3A 0.0(6) . . . . ?
P1A C1A C2A C3A -178.4(3) . . . . ?
C1A C2A C3A C4A 1.5(7) . . . . ?
C2A C3A C4A C5A -1.7(7) . . . . ?
C3A C4A C5A C6A 0.3(7) . . . . ?
C4A C5A C6A C1A 1.2(7) . . . . ?
C2A C1A C6A C5A -1.3(6) . . . . ?
P1A C1A C6A C5A 177.1(3) . . . . ?
C12A C7A C8A C9A -0.3(6) . . . . ?
P1A C7A C8A C9A -179.6(3) . . . . ?
C7A C8A C9A C10A 0.6(7) . . . . ?
C8A C9A C10A C11A 0.0(7) . . . . ?
C9A C10A C11A C12A -0.9(7) . . . . ?
C8A C7A C12A C11A -0.6(6) . . . . ?
P1A C7A C12A C11A 178.7(3) . . . . ?
C10A C11A C12A C7A 1.2(6) . . . . ?
C8A C7A P1A O1A -139.2(3) . . . . ?
C12A C7A P1A O1A 41.5(4) . . . . ?
C8A C7A P1A C13A -12.7(4) . . . . ?
C12A C7A P1A C13A 168.0(3) . . . . ?
C8A C7A P1A C1A 100.0(4) . . . . ?
C12A C7A P1A C1A -79.3(3) . . . . ?
C2A C1A P1A O1A 10.7(4) . . . . ?
C6A C1A P1A O1A -167.7(3) . . . . ?
C2A C1A P1A C13A -114.6(3) . . . . ?
C6A C1A P1A C13A 67.0(4) . . . . ?
C2A C1A P1A C7A 132.3(3) . . . . ?
C6A C1A P1A C7A -46.1(4) . . . . ?
C3B C1B C2B F1B -178.6(4) 5_765 . . . ?
I1B C1B C2B F1B 2.2(6) . . . . ?
C3B C1B C2B C3B 1.7(7) 5_765 . . . ?
I1B C1B C2B C3B -177.6(3) . . . . ?
F1B C2B C3B F2B -1.0(6) . . . . ?
C1B C2B C3B F2B 178.8(4) . . . . ?
F1B C2B C3B C1B 178.5(4) . . . 5_765 ?
C1B C2B C3B C1B -1.7(7) . . . 5_765 ?

_refine_diff_density_max         0.701
_refine_diff_density_min         -1.112
_refine_diff_density_rms         0.108


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: nitromethane'
####################################################################### 
# 
# 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_tric_2mdppo_14tfib_123K
_database_code_depnum_ccdc_archive 'CCDC 1831926'
loop_
_audit_author_name
_audit_author_address
'Filip Topic'
;McGill University
Canada
;
_audit_update_record             
;
2018-03-23 deposited with the CCDC.	2019-10-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_formula_moiety         '2(C13 H13 O P), C6 F4 I2'
_chemical_formula_sum            'C32 H26 F4 I2 O2 P2'
_chemical_formula_weight         834.27

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'
F F 0.0171 0.0103 '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'
O O 0.0106 0.0060 '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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.0447(4)
_cell_length_b                   11.5656(6)
_cell_length_c                   12.5757(7)
_cell_angle_alpha                113.430(5)
_cell_angle_beta                 100.733(5)
_cell_angle_gamma                97.582(5)
_cell_volume                     771.60(8)
_cell_formula_units_Z            1
_cell_measurement_temperature    123.0(1)
_cell_measurement_reflns_used    3008
_cell_measurement_theta_min      3.5190
_cell_measurement_theta_max      29.2260

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.795
_exptl_crystal_F_000             406
_exptl_crystal_size_max          0.334
_exptl_crystal_size_mid          0.174
_exptl_crystal_size_min          0.138
_exptl_absorpt_coefficient_mu    2.195
_shelx_estimated_absorpt_T_min   0.528
_shelx_estimated_absorpt_T_max   0.752
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_correction_T_min  0.620
_exptl_absorpt_correction_T_max  0.766
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Numerical absorption correction based on gaussian integration over
 a multifaceted crystal model.
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_diffrn_ambient_temperature      123.0(1)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_detector_area_resol_mean 5.1977
_diffrn_reflns_number            5563
_diffrn_reflns_av_unetI/netI     0.0366
_diffrn_reflns_av_R_equivalents  0.0200
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.219
_diffrn_reflns_theta_max         29.455
_diffrn_reflns_theta_full        25.250
_diffrn_measured_fraction_theta_max 0.829
_diffrn_measured_fraction_theta_full 0.992
_diffrn_reflns_Laue_measured_fraction_max 0.829
_diffrn_reflns_Laue_measured_fraction_full 0.992
_diffrn_reflns_point_group_measured_fraction_max 0.829
_diffrn_reflns_point_group_measured_fraction_full 0.992
_reflns_number_total             3547
_reflns_number_gt                3289
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2015)'
_computing_publication_material  
'OLEX2 (Dolomanov et al., 2009) & WinGX (Farrugia, 2012)'

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0401P)²+0.2956P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3547
_refine_ls_number_parameters     191
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0327
_refine_ls_R_factor_gt           0.0295
_refine_ls_wR_factor_ref         0.0738
_refine_ls_wR_factor_gt          0.0705
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_restrained_S_all      1.058
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1B C 0.5135(5) 0.1276(3) 0.0844(3) 0.0185(6) Uani 1 1 d . . . . .
C2B C 0.6980(5) 0.0690(3) 0.0900(3) 0.0219(6) Uani 1 1 d . . . . .
C3B C 0.6838(5) -0.0551(3) 0.0084(3) 0.0220(6) Uani 1 1 d . . . . .
F1B F 0.8940(3) 0.13368(17) 0.17659(17) 0.0304(4) Uani 1 1 d . . . . .
F2B F 0.8701(3) -0.10667(17) 0.01926(18) 0.0304(4) Uani 1 1 d . . . . .
I1B I 0.53710(3) 0.31551(2) 0.20959(2) 0.01911(8) Uani 1 1 d . . . . .
C1A C 0.4409(5) 0.7851(3) 0.5067(3) 0.0183(6) Uani 1 1 d . . . . .
C2A C 0.6582(5) 0.8373(3) 0.5859(3) 0.0262(7) Uani 1 1 d . . . . .
H2A H 0.777397 0.791342 0.573433 0.031 Uiso 1 1 calc R U . . .
C3A C 0.7021(6) 0.9564(3) 0.6835(3) 0.0308(7) Uani 1 1 d . . . . .
H3A H 0.850993 0.991166 0.738566 0.037 Uiso 1 1 calc R U . . .
C4A C 0.5331(6) 1.0250(3) 0.7018(3) 0.0300(7) Uani 1 1 d . . . . .
H4A H 0.565658 1.107608 0.768017 0.036 Uiso 1 1 calc R U . . .
C5A C 0.3178(6) 0.9735(4) 0.6239(4) 0.0422(10) Uani 1 1 d . . . . .
H5A H 0.199906 1.020284 0.637076 0.051 Uiso 1 1 calc R U . . .
C6A C 0.2693(6) 0.8546(4) 0.5264(3) 0.0396(9) Uani 1 1 d . . . . .
H6A H 0.118920 0.820066 0.472747 0.048 Uiso 1 1 calc R U . . .
C7A C 0.2659(5) 0.6395(2) 0.2474(2) 0.0164(5) Uani 1 1 d . . . . .
C8A C 0.0507(5) 0.6702(3) 0.2229(3) 0.0211(6) Uani 1 1 d . . . . .
H8A H -0.043200 0.680665 0.277359 0.025 Uiso 1 1 calc R U . . .
C9A C -0.0244(5) 0.6851(3) 0.1191(3) 0.0239(6) Uani 1 1 d . . . . .
H9A H -0.167783 0.708593 0.104064 0.029 Uiso 1 1 calc R U . . .
C10A C 0.1071(5) 0.6661(3) 0.0367(3) 0.0213(6) Uani 1 1 d . . . . .
H10A H 0.054730 0.676942 -0.034076 0.026 Uiso 1 1 calc R U . . .
C11A C 0.3164(5) 0.6311(3) 0.0587(3) 0.0214(6) Uani 1 1 d . . . . .
H11A H 0.405382 0.615554 0.001691 0.026 Uiso 1 1 calc R U . . .
C12A C 0.3954(5) 0.6187(3) 0.1636(3) 0.0182(6) Uani 1 1 d . . . . .
H12A H 0.539460 0.595854 0.178465 0.022 Uiso 1 1 calc R U . . .
C13A C 0.1647(5) 0.5264(3) 0.4049(3) 0.0232(6) Uani 1 1 d . . . . .
H13A H 0.222626 0.518143 0.479132 0.035 Uiso 1 1 calc R U . . .
H13B H 0.119353 0.440494 0.336694 0.035 Uiso 1 1 calc R U . . .
H13C H 0.030398 0.565348 0.410531 0.035 Uiso 1 1 calc R U . . .
O1A O 0.6026(3) 0.57700(19) 0.37724(19) 0.0196(4) Uani 1 1 d . . . . .
P1A P 0.38636(12) 0.62659(7) 0.38376(7) 0.01550(15) 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
C1B C2B 1.385(4) . ?
C1B C3B 1.388(4) 2_655 ?
C1B I1B 2.082(3) . ?
C2B F1B 1.336(3) . ?
C2B C3B 1.372(4) . ?
C3B F2B 1.352(3) . ?
C1A C2A 1.381(4) . ?
C1A C6A 1.393(4) . ?
C1A P1A 1.805(3) . ?
C2A C3A 1.383(5) . ?
C2A H2A 0.9500 . ?
C3A C4A 1.371(5) . ?
C3A H3A 0.9500 . ?
C4A C5A 1.366(5) . ?
C4A H4A 0.9500 . ?
C5A C6A 1.378(5) . ?
C5A H5A 0.9500 . ?
C6A H6A 0.9500 . ?
C7A C12A 1.392(4) . ?
C7A C8A 1.405(4) . ?
C7A P1A 1.805(3) . ?
C8A C9A 1.386(4) . ?
C8A H8A 0.9500 . ?
C9A C10A 1.387(4) . ?
C9A H9A 0.9500 . ?
C10A C11A 1.391(4) . ?
C10A H10A 0.9500 . ?
C11A C12A 1.387(4) . ?
C11A H11A 0.9500 . ?
C12A H12A 0.9500 . ?
C13A P1A 1.782(3) . ?
C13A H13A 0.9800 . ?
C13A H13B 0.9800 . ?
C13A H13C 0.9800 . ?
O1A P1A 1.4980(19) . ?

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
C2B C1B C3B 116.6(3) . 2_655 ?
C2B C1B I1B 120.8(2) . . ?
C3B C1B I1B 122.7(2) 2_655 . ?
F1B C2B C3B 119.1(3) . . ?
F1B C2B C1B 119.7(3) . . ?
C3B C2B C1B 121.2(3) . . ?
F2B C3B C2B 118.2(3) . . ?
F2B C3B C1B 119.6(3) . 2_655 ?
C2B C3B C1B 122.2(3) . 2_655 ?
C2A C1A C6A 119.0(3) . . ?
C2A C1A P1A 118.8(2) . . ?
C6A C1A P1A 122.2(2) . . ?
C1A C2A C3A 119.9(3) . . ?
C1A C2A H2A 120.0 . . ?
C3A C2A H2A 120.0 . . ?
C4A C3A C2A 120.8(3) . . ?
C4A C3A H3A 119.6 . . ?
C2A C3A H3A 119.6 . . ?
C5A C4A C3A 119.5(3) . . ?
C5A C4A H4A 120.3 . . ?
C3A C4A H4A 120.3 . . ?
C4A C5A C6A 120.9(3) . . ?
C4A C5A H5A 119.6 . . ?
C6A C5A H5A 119.6 . . ?
C5A C6A C1A 119.9(3) . . ?
C5A C6A H6A 120.0 . . ?
C1A C6A H6A 120.0 . . ?
C12A C7A C8A 119.0(3) . . ?
C12A C7A P1A 117.7(2) . . ?
C8A C7A P1A 123.3(2) . . ?
C9A C8A C7A 119.9(3) . . ?
C9A C8A H8A 120.1 . . ?
C7A C8A H8A 120.1 . . ?
C8A C9A C10A 120.8(3) . . ?
C8A C9A H9A 119.6 . . ?
C10A C9A H9A 119.6 . . ?
C9A C10A C11A 119.4(3) . . ?
C9A C10A H10A 120.3 . . ?
C11A C10A H10A 120.3 . . ?
C12A C11A C10A 120.2(3) . . ?
C12A C11A H11A 119.9 . . ?
C10A C11A H11A 119.9 . . ?
C11A C12A C7A 120.7(3) . . ?
C11A C12A H12A 119.6 . . ?
C7A C12A H12A 119.6 . . ?
P1A C13A H13A 109.5 . . ?
P1A C13A H13B 109.5 . . ?
H13A C13A H13B 109.5 . . ?
P1A C13A H13C 109.5 . . ?
H13A C13A H13C 109.5 . . ?
H13B C13A H13C 109.5 . . ?
O1A P1A C13A 113.66(13) . . ?
O1A P1A C1A 111.65(13) . . ?
C13A P1A C1A 106.13(14) . . ?
O1A P1A C7A 110.73(13) . . ?
C13A P1A C7A 106.90(14) . . ?
C1A P1A C7A 107.40(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
C3B C1B C2B F1B 179.5(3) 2_655 . . . ?
I1B C1B C2B F1B -0.2(4) . . . . ?
C3B C1B C2B C3B -0.8(5) 2_655 . . . ?
I1B C1B C2B C3B 179.6(2) . . . . ?
F1B C2B C3B F2B -0.1(4) . . . . ?
C1B C2B C3B F2B -179.8(3) . . . . ?
F1B C2B C3B C1B -179.4(3) . . . 2_655 ?
C1B C2B C3B C1B 0.8(5) . . . 2_655 ?
C6A C1A C2A C3A 0.4(5) . . . . ?
P1A C1A C2A C3A -177.5(3) . . . . ?
C1A C2A C3A C4A -1.1(5) . . . . ?
C2A C3A C4A C5A 1.4(5) . . . . ?
C3A C4A C5A C6A -1.0(6) . . . . ?
C4A C5A C6A C1A 0.3(7) . . . . ?
C2A C1A C6A C5A 0.0(6) . . . . ?
P1A C1A C6A C5A 177.9(3) . . . . ?
C12A C7A C8A C9A -2.9(4) . . . . ?
P1A C7A C8A C9A 176.5(2) . . . . ?
C7A C8A C9A C10A 2.0(5) . . . . ?
C8A C9A C10A C11A 0.3(4) . . . . ?
C9A C10A C11A C12A -1.7(4) . . . . ?
C10A C11A C12A C7A 0.8(4) . . . . ?
C8A C7A C12A C11A 1.5(4) . . . . ?
P1A C7A C12A C11A -178.0(2) . . . . ?
C2A C1A P1A O1A -6.2(3) . . . . ?
C6A C1A P1A O1A 175.9(3) . . . . ?
C2A C1A P1A C13A 118.1(3) . . . . ?
C6A C1A P1A C13A -59.7(3) . . . . ?
C2A C1A P1A C7A -127.8(2) . . . . ?
C6A C1A P1A C7A 54.4(3) . . . . ?
C12A C7A P1A O1A -7.5(3) . . . . ?
C8A C7A P1A O1A 173.1(2) . . . . ?
C12A C7A P1A C13A -131.8(2) . . . . ?
C8A C7A P1A C13A 48.7(3) . . . . ?
C12A C7A P1A C1A 114.7(2) . . . . ?
C8A C7A P1A C1A -64.8(3) . . . . ?

_refine_diff_density_max         1.072
_refine_diff_density_min         -1.884
_refine_diff_density_rms         0.118


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetonitrile'
####################################################################### 
# 
# 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_mdppo_123K
_database_code_depnum_ccdc_archive 'CCDC 1831928'
loop_
_audit_author_name
_audit_author_address
'Filip Topic'
;McGill University
Canada
;
_audit_update_record             
;
2018-03-23 deposited with the CCDC.	2019-10-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_formula_moiety         'C13 H13 O P'
_chemical_formula_sum            'C13 H13 O P'
_chemical_formula_weight         216.20

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'
O O 0.0106 0.0060 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   8.6356(4)
_cell_length_b                   24.2366(12)
_cell_length_c                   16.6059(9)
_cell_angle_alpha                90
_cell_angle_beta                 101.535(5)
_cell_angle_gamma                90
_cell_volume                     3405.4(3)
_cell_formula_units_Z            12
_cell_measurement_temperature    123.0(1)
_cell_measurement_reflns_used    4911
_cell_measurement_theta_min      2.5750
_cell_measurement_theta_max      30.5330

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.265
_exptl_crystal_F_000             1368
_exptl_crystal_size_max          0.420
_exptl_crystal_size_mid          0.270
_exptl_crystal_size_min          0.090
_exptl_absorpt_coefficient_mu    0.211
_shelx_estimated_absorpt_T_min   0.916
_shelx_estimated_absorpt_T_max   0.981
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.94615
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.46 (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_diffrn_ambient_temperature      123.0(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_method       'φ scans + ω scans'
_diffrn_detector_area_resol_mean 9
_diffrn_reflns_number            17889
_diffrn_reflns_av_unetI/netI     0.0680
_diffrn_reflns_av_R_equivalents  0.0336
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -31
_diffrn_reflns_limit_k_max       33
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_theta_min         2.095
_diffrn_reflns_theta_max         30.935
_diffrn_reflns_theta_full        25.250
_diffrn_measured_fraction_theta_max 0.844
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.844
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.844
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             9114
_reflns_number_gt                5590
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_cell_refinement       'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.46 (Rigaku OD, 2015)'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2015)'
_computing_publication_material  
'OLEX2 (Dolomanov et al., 2009) & WinGX publication routines (Farrugia, 2012)'

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0547P)²+0.9666P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         9114
_refine_ls_number_parameters     409
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1060
_refine_ls_R_factor_gt           0.0587
_refine_ls_wR_factor_ref         0.1480
_refine_ls_wR_factor_gt          0.1236
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_restrained_S_all      1.025
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1A C 0.3009(2) 0.16481(8) 0.23189(13) 0.0210(4) Uani 1 1 d . . . . .
C2A C 0.4535(2) 0.14895(9) 0.27011(14) 0.0274(5) Uani 1 1 d . . . . .
H2A H 0.473582 0.136578 0.325504 0.033 Uiso 1 1 calc R U . . .
C3A C 0.5764(3) 0.15128(10) 0.22694(16) 0.0353(6) Uani 1 1 d . . . . .
H3A H 0.679077 0.139058 0.252295 0.042 Uiso 1 1 calc R U . . .
C4A C 0.5491(3) 0.17139(10) 0.14711(16) 0.0365(6) Uani 1 1 d . . . . .
H4A H 0.632970 0.173234 0.117919 0.044 Uiso 1 1 calc R U . . .
C5A C 0.3989(3) 0.18875(10) 0.11025(15) 0.0362(6) Uani 1 1 d . . . . .
H5A H 0.380837 0.203427 0.056129 0.043 Uiso 1 1 calc R U . . .
C6A C 0.2738(3) 0.18496(9) 0.15161(13) 0.0295(5) Uani 1 1 d . . . . .
H6A H 0.170556 0.196051 0.125234 0.035 Uiso 1 1 calc R U . . .
C7A C 0.0801(2) 0.08464(8) 0.27063(12) 0.0216(4) Uani 1 1 d . . . . .
C8A C 0.1133(3) 0.05352(9) 0.20590(14) 0.0317(5) Uani 1 1 d . . . . .
H8A H 0.171416 0.069677 0.169057 0.038 Uiso 1 1 calc R U . . .
C9A C 0.0631(3) -0.00065(9) 0.19421(16) 0.0375(6) Uani 1 1 d . . . . .
H9A H 0.087552 -0.021417 0.149867 0.045 Uiso 1 1 calc R U . . .
C10A C -0.0223(3) -0.02446(9) 0.24668(15) 0.0372(6) Uani 1 1 d . . . . .
H10A H -0.057032 -0.061602 0.238549 0.045 Uiso 1 1 calc R U . . .
C11A C -0.0572(3) 0.00575(10) 0.31111(16) 0.0438(7) Uani 1 1 d . . . . .
H11A H -0.116402 -0.010613 0.347271 0.053 Uiso 1 1 calc R U . . .
C12A C -0.0060(3) 0.06014(10) 0.32344(15) 0.0352(6) Uani 1 1 d . . . . .
H12A H -0.029982 0.080632 0.368157 0.042 Uiso 1 1 calc R U . . .
C13A C -0.0138(2) 0.19888(8) 0.24372(13) 0.0240(5) Uani 1 1 d . . . . .
H13A H -0.096525 0.197691 0.276376 0.036 Uiso 1 1 calc R U . . .
H13B H -0.056975 0.185947 0.187820 0.036 Uiso 1 1 calc R U . . .
H13C H 0.024188 0.236849 0.241623 0.036 Uiso 1 1 calc R U . . .
O1A O 0.20319(17) 0.16505(6) 0.38014(8) 0.0251(3) Uani 1 1 d . . . . .
P1A P 0.14699(6) 0.15525(2) 0.29003(3) 0.01890(13) Uani 1 1 d . . . . .
C1B C 0.6335(2) 0.16347(8) 0.56398(12) 0.0218(4) Uani 1 1 d . . . . .
C2B C 0.7791(3) 0.13783(9) 0.59264(14) 0.0293(5) Uani 1 1 d . . . . .
H2B H 0.795280 0.116767 0.641865 0.035 Uiso 1 1 calc R U . . .
C3B C 0.9006(3) 0.14314(10) 0.54905(15) 0.0343(6) Uani 1 1 d . . . . .
H3B H 0.998714 0.125113 0.568151 0.041 Uiso 1 1 calc R U . . .
C4B C 0.8787(3) 0.17460(10) 0.47798(15) 0.0346(6) Uani 1 1 d . . . . .
H4B H 0.962204 0.178553 0.448872 0.041 Uiso 1 1 calc R U . . .
C5B C 0.7352(3) 0.20022(10) 0.44952(15) 0.0350(6) Uani 1 1 d . . . . .
H5B H 0.720248 0.221773 0.400794 0.042 Uiso 1 1 calc R U . . .
C6B C 0.6122(3) 0.19451(9) 0.49216(14) 0.0296(5) Uani 1 1 d . . . . .
H6B H 0.513442 0.211909 0.472015 0.036 Uiso 1 1 calc R U . . .
C7B C 0.4232(2) 0.08104(8) 0.60033(13) 0.0221(4) Uani 1 1 d . . . . .
C8B C 0.3195(3) 0.06400(9) 0.52859(13) 0.0276(5) Uani 1 1 d . . . . .
H8B H 0.269792 0.090571 0.489847 0.033 Uiso 1 1 calc R U . . .
C9B C 0.2896(3) 0.00812(9) 0.51426(15) 0.0338(6) Uani 1 1 d . . . . .
H9B H 0.218561 -0.003376 0.465858 0.041 Uiso 1 1 calc R U . . .
C10B C 0.3625(3) -0.03085(10) 0.57009(16) 0.0386(6) Uani 1 1 d . . . . .
H10B H 0.341503 -0.068971 0.559977 0.046 Uiso 1 1 calc R U . . .
C11B C 0.4662(3) -0.01430(10) 0.64064(16) 0.0431(7) Uani 1 1 d . . . . .
H11B H 0.516942 -0.041123 0.678659 0.052 Uiso 1 1 calc R U . . .
C12B C 0.4960(3) 0.04109(9) 0.65595(14) 0.0335(6) Uani 1 1 d . . . . .
H12B H 0.566745 0.052147 0.704709 0.040 Uiso 1 1 calc R U . . .
C13B C 0.3160(2) 0.19476(8) 0.57868(13) 0.0239(5) Uani 1 1 d . . . . .
H13D H 0.231618 0.190231 0.609793 0.036 Uiso 1 1 calc R U . . .
H13E H 0.276786 0.183950 0.521357 0.036 Uiso 1 1 calc R U . . .
H13F H 0.349498 0.233456 0.580823 0.036 Uiso 1 1 calc R U . . .
O1B O 0.54012(17) 0.16079(6) 0.71284(8) 0.0250(3) Uani 1 1 d . . . . .
P1B P 0.48049(6) 0.15210(2) 0.62263(3) 0.01861(13) Uani 1 1 d . . . . .
C1C C 0.9533(2) 0.16234(8) 0.89390(12) 0.0202(4) Uani 1 1 d . . . . .
C2C C 1.1046(2) 0.14284(9) 0.92882(14) 0.0257(5) Uani 1 1 d . . . . .
H2C H 1.124220 0.127355 0.982459 0.031 Uiso 1 1 calc R U . . .
C3C C 1.2261(3) 0.14607(9) 0.88526(15) 0.0310(5) Uani 1 1 d . . . . .
H3C H 1.327891 0.132059 0.908755 0.037 Uiso 1 1 calc R U . . .
C4C C 1.1992(3) 0.16971(9) 0.80750(14) 0.0310(5) Uani 1 1 d . . . . .
H4C H 1.282713 0.172273 0.778124 0.037 Uiso 1 1 calc R U . . .
C5C C 1.0504(3) 0.18953(10) 0.77292(14) 0.0321(5) Uani 1 1 d . . . . .
H5C H 1.032280 0.205941 0.719911 0.039 Uiso 1 1 calc R U . . .
C6C C 0.9268(3) 0.18555(9) 0.81548(13) 0.0277(5) Uani 1 1 d . . . . .
H6C H 0.824501 0.198664 0.790989 0.033 Uiso 1 1 calc R U . . .
C7C C 0.7302(2) 0.08828(8) 0.94810(13) 0.0221(4) Uani 1 1 d . . . . .
C8C C 0.6165(3) 0.06985(9) 0.88065(14) 0.0275(5) Uani 1 1 d . . . . .
H8C H 0.574544 0.094583 0.837392 0.033 Uiso 1 1 calc R U . . .
C9C C 0.5657(3) 0.01540(9) 0.87750(15) 0.0353(6) Uani 1 1 d . . . . .
H9C H 0.487282 0.003097 0.832567 0.042 Uiso 1 1 calc R U . . .
C10C C 0.6292(3) -0.02114(10) 0.93976(17) 0.0394(6) Uani 1 1 d . . . . .
H10C H 0.595584 -0.058536 0.936632 0.047 Uiso 1 1 calc R U . . .
C11C C 0.7407(3) -0.00344(10) 1.00611(16) 0.0401(6) Uani 1 1 d . . . . .
H11C H 0.783488 -0.028637 1.048577 0.048 Uiso 1 1 calc R U . . .
C12C C 0.7905(3) 0.05109(9) 1.01098(14) 0.0312(5) Uani 1 1 d . . . . .
H12C H 0.866051 0.063244 1.057274 0.037 Uiso 1 1 calc R U . . .
C13C C 0.6450(2) 0.20187(8) 0.91152(13) 0.0234(5) Uani 1 1 d . . . . .
H13G H 0.563764 0.201433 0.945105 0.035 Uiso 1 1 calc R U . . .
H13H H 0.599648 0.188548 0.856103 0.035 Uiso 1 1 calc R U . . .
H13I H 0.683911 0.239631 0.908287 0.035 Uiso 1 1 calc R U . . .
O1C O 0.87692(17) 0.17105(6) 1.04517(8) 0.0260(3) Uani 1 1 d . . . . .
P1C P 0.80567(6) 0.15795(2) 0.95736(3) 0.01864(13) 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
C1A C6A 1.395(3) . ?
C1A C2A 1.397(3) . ?
C1A P1A 1.807(2) . ?
C2A C3A 1.395(3) . ?
C2A H2A 0.9500 . ?
C3A C4A 1.388(3) . ?
C3A H3A 0.9500 . ?
C4A C5A 1.384(3) . ?
C4A H4A 0.9500 . ?
C5A C6A 1.394(3) . ?
C5A H5A 0.9500 . ?
C6A H6A 0.9500 . ?
C7A C8A 1.389(3) . ?
C7A C12A 1.391(3) . ?
C7A P1A 1.814(2) . ?
C8A C9A 1.384(3) . ?
C8A H8A 0.9500 . ?
C9A C10A 1.375(3) . ?
C9A H9A 0.9500 . ?
C10A C11A 1.379(3) . ?
C10A H10A 0.9500 . ?
C11A C12A 1.392(3) . ?
C11A H11A 0.9500 . ?
C12A H12A 0.9500 . ?
C13A P1A 1.792(2) . ?
C13A H13A 0.9800 . ?
C13A H13B 0.9800 . ?
C13A H13C 0.9800 . ?
O1A P1A 1.4969(14) . ?
C1B C6B 1.391(3) . ?
C1B C2B 1.398(3) . ?
C1B P1B 1.812(2) . ?
C2B C3B 1.395(3) . ?
C2B H2B 0.9500 . ?
C3B C4B 1.386(3) . ?
C3B H3B 0.9500 . ?
C4B C5B 1.382(3) . ?
C4B H4B 0.9500 . ?
C5B C6B 1.397(3) . ?
C5B H5B 0.9500 . ?
C6B H6B 0.9500 . ?
C7B C12B 1.398(3) . ?
C7B C8B 1.402(3) . ?
C7B P1B 1.810(2) . ?
C8B C9B 1.390(3) . ?
C8B H8B 0.9500 . ?
C9B C10B 1.384(3) . ?
C9B H9B 0.9500 . ?
C10B C11B 1.384(3) . ?
C10B H10B 0.9500 . ?
C11B C12B 1.381(3) . ?
C11B H11B 0.9500 . ?
C12B H12B 0.9500 . ?
C13B P1B 1.790(2) . ?
C13B H13D 0.9800 . ?
C13B H13E 0.9800 . ?
C13B H13F 0.9800 . ?
O1B P1B 1.4984(14) . ?
C1C C6C 1.395(3) . ?
C1C C2C 1.401(3) . ?
C1C P1C 1.812(2) . ?
C2C C3C 1.391(3) . ?
C2C H2C 0.9500 . ?
C3C C4C 1.389(3) . ?
C3C H3C 0.9500 . ?
C4C C5C 1.385(3) . ?
C4C H4C 0.9500 . ?
C5C C6C 1.397(3) . ?
C5C H5C 0.9500 . ?
C6C H6C 0.9500 . ?
C7C C12C 1.399(3) . ?
C7C C8C 1.407(3) . ?
C7C P1C 1.805(2) . ?
C8C C9C 1.388(3) . ?
C8C H8C 0.9500 . ?
C9C C10C 1.388(3) . ?
C9C H9C 0.9500 . ?
C10C C11C 1.379(4) . ?
C10C H10C 0.9500 . ?
C11C C12C 1.387(3) . ?
C11C H11C 0.9500 . ?
C12C H12C 0.9500 . ?
C13C P1C 1.793(2) . ?
C13C H13G 0.9800 . ?
C13C H13H 0.9800 . ?
C13C H13I 0.9800 . ?
O1C P1C 1.4990(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
C6A C1A C2A 119.55(19) . . ?
C6A C1A P1A 123.68(16) . . ?
C2A C1A P1A 116.73(16) . . ?
C3A C2A C1A 120.0(2) . . ?
C3A C2A H2A 120.0 . . ?
C1A C2A H2A 120.0 . . ?
C4A C3A C2A 120.2(2) . . ?
C4A C3A H3A 119.9 . . ?
C2A C3A H3A 119.9 . . ?
C5A C4A C3A 119.6(2) . . ?
C5A C4A H4A 120.2 . . ?
C3A C4A H4A 120.2 . . ?
C4A C5A C6A 120.8(2) . . ?
C4A C5A H5A 119.6 . . ?
C6A C5A H5A 119.6 . . ?
C5A C6A C1A 119.7(2) . . ?
C5A C6A H6A 120.2 . . ?
C1A C6A H6A 120.2 . . ?
C8A C7A C12A 118.4(2) . . ?
C8A C7A P1A 122.82(16) . . ?
C12A C7A P1A 118.81(16) . . ?
C9A C8A C7A 121.1(2) . . ?
C9A C8A H8A 119.5 . . ?
C7A C8A H8A 119.5 . . ?
C10A C9A C8A 120.1(2) . . ?
C10A C9A H9A 119.9 . . ?
C8A C9A H9A 119.9 . . ?
C9A C10A C11A 119.8(2) . . ?
C9A C10A H10A 120.1 . . ?
C11A C10A H10A 120.1 . . ?
C10A C11A C12A 120.3(2) . . ?
C10A C11A H11A 119.8 . . ?
C12A C11A H11A 119.8 . . ?
C7A C12A C11A 120.4(2) . . ?
C7A C12A H12A 119.8 . . ?
C11A C12A H12A 119.8 . . ?
P1A C13A H13A 109.5 . . ?
P1A C13A H13B 109.5 . . ?
H13A C13A H13B 109.5 . . ?
P1A C13A H13C 109.5 . . ?
H13A C13A H13C 109.5 . . ?
H13B C13A H13C 109.5 . . ?
O1A P1A C13A 113.83(9) . . ?
O1A P1A C1A 112.81(9) . . ?
C13A P1A C1A 106.54(10) . . ?
O1A P1A C7A 110.80(9) . . ?
C13A P1A C7A 106.77(10) . . ?
C1A P1A C7A 105.55(9) . . ?
C6B C1B C2B 119.22(19) . . ?
C6B C1B P1B 123.88(17) . . ?
C2B C1B P1B 116.88(16) . . ?
C3B C2B C1B 120.1(2) . . ?
C3B C2B H2B 120.0 . . ?
C1B C2B H2B 120.0 . . ?
C4B C3B C2B 120.3(2) . . ?
C4B C3B H3B 119.9 . . ?
C2B C3B H3B 119.9 . . ?
C5B C4B C3B 119.9(2) . . ?
C5B C4B H4B 120.0 . . ?
C3B C4B H4B 120.0 . . ?
C4B C5B C6B 120.2(2) . . ?
C4B C5B H5B 119.9 . . ?
C6B C5B H5B 119.9 . . ?
C1B C6B C5B 120.3(2) . . ?
C1B C6B H6B 119.8 . . ?
C5B C6B H6B 119.8 . . ?
C12B C7B C8B 119.0(2) . . ?
C12B C7B P1B 117.10(17) . . ?
C8B C7B P1B 123.80(16) . . ?
C9B C8B C7B 119.9(2) . . ?
C9B C8B H8B 120.1 . . ?
C7B C8B H8B 120.1 . . ?
C10B C9B C8B 120.4(2) . . ?
C10B C9B H9B 119.8 . . ?
C8B C9B H9B 119.8 . . ?
C11B C10B C9B 120.0(2) . . ?
C11B C10B H10B 120.0 . . ?
C9B C10B H10B 120.0 . . ?
C12B C11B C10B 120.2(2) . . ?
C12B C11B H11B 119.9 . . ?
C10B C11B H11B 119.9 . . ?
C11B C12B C7B 120.6(2) . . ?
C11B C12B H12B 119.7 . . ?
C7B C12B H12B 119.7 . . ?
P1B C13B H13D 109.5 . . ?
P1B C13B H13E 109.5 . . ?
H13D C13B H13E 109.5 . . ?
P1B C13B H13F 109.5 . . ?
H13D C13B H13F 109.5 . . ?
H13E C13B H13F 109.5 . . ?
O1B P1B C13B 114.36(9) . . ?
O1B P1B C7B 111.32(9) . . ?
C13B P1B C7B 107.70(10) . . ?
O1B P1B C1B 111.97(9) . . ?
C13B P1B C1B 107.30(10) . . ?
C7B P1B C1B 103.52(9) . . ?
C6C C1C C2C 119.19(19) . . ?
C6C C1C P1C 124.29(16) . . ?
C2C C1C P1C 116.46(15) . . ?
C3C C2C C1C 120.3(2) . . ?
C3C C2C H2C 119.9 . . ?
C1C C2C H2C 119.9 . . ?
C4C C3C C2C 120.2(2) . . ?
C4C C3C H3C 119.9 . . ?
C2C C3C H3C 119.9 . . ?
C5C C4C C3C 119.8(2) . . ?
C5C C4C H4C 120.1 . . ?
C3C C4C H4C 120.1 . . ?
C4C C5C C6C 120.4(2) . . ?
C4C C5C H5C 119.8 . . ?
C6C C5C H5C 119.8 . . ?
C1C C6C C5C 120.1(2) . . ?
C1C C6C H6C 120.0 . . ?
C5C C6C H6C 120.0 . . ?
C12C C7C C8C 119.1(2) . . ?
C12C C7C P1C 117.71(17) . . ?
C8C C7C P1C 123.19(16) . . ?
C9C C8C C7C 119.8(2) . . ?
C9C C8C H8C 120.1 . . ?
C7C C8C H8C 120.1 . . ?
C10C C9C C8C 120.3(2) . . ?
C10C C9C H9C 119.9 . . ?
C8C C9C H9C 119.9 . . ?
C11C C10C C9C 120.4(2) . . ?
C11C C10C H10C 119.8 . . ?
C9C C10C H10C 119.8 . . ?
C10C C11C C12C 120.1(2) . . ?
C10C C11C H11C 119.9 . . ?
C12C C11C H11C 119.9 . . ?
C11C C12C C7C 120.4(2) . . ?
C11C C12C H12C 119.8 . . ?
C7C C12C H12C 119.8 . . ?
P1C C13C H13G 109.5 . . ?
P1C C13C H13H 109.5 . . ?
H13G C13C H13H 109.5 . . ?
P1C C13C H13I 109.5 . . ?
H13G C13C H13I 109.5 . . ?
H13H C13C H13I 109.5 . . ?
O1C P1C C13C 114.80(9) . . ?
O1C P1C C7C 110.61(9) . . ?
C13C P1C C7C 106.49(10) . . ?
O1C P1C C1C 110.71(9) . . ?
C13C P1C C1C 107.02(10) . . ?
C7C P1C C1C 106.81(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
C6A C1A C2A C3A -2.5(3) . . . . ?
P1A C1A C2A C3A 175.30(17) . . . . ?
C1A C2A C3A C4A 2.6(3) . . . . ?
C2A C3A C4A C5A -0.5(4) . . . . ?
C3A C4A C5A C6A -1.7(4) . . . . ?
C4A C5A C6A C1A 1.7(4) . . . . ?
C2A C1A C6A C5A 0.4(3) . . . . ?
P1A C1A C6A C5A -177.27(17) . . . . ?
C12A C7A C8A C9A -0.4(3) . . . . ?
P1A C7A C8A C9A 178.58(19) . . . . ?
C7A C8A C9A C10A 0.5(4) . . . . ?
C8A C9A C10A C11A -0.2(4) . . . . ?
C9A C10A C11A C12A -0.2(4) . . . . ?
C8A C7A C12A C11A -0.1(4) . . . . ?
P1A C7A C12A C11A -179.0(2) . . . . ?
C10A C11A C12A C7A 0.4(4) . . . . ?
C6A C1A P1A O1A -147.06(17) . . . . ?
C2A C1A P1A O1A 35.23(19) . . . . ?
C6A C1A P1A C13A -21.5(2) . . . . ?
C2A C1A P1A C13A 160.83(16) . . . . ?
C6A C1A P1A C7A 91.81(19) . . . . ?
C2A C1A P1A C7A -85.90(18) . . . . ?
C8A C7A P1A O1A -138.83(18) . . . . ?
C12A C7A P1A O1A 40.1(2) . . . . ?
C8A C7A P1A C13A 96.7(2) . . . . ?
C12A C7A P1A C13A -84.3(2) . . . . ?
C8A C7A P1A C1A -16.4(2) . . . . ?
C12A C7A P1A C1A 162.54(18) . . . . ?
C6B C1B C2B C3B -0.5(3) . . . . ?
P1B C1B C2B C3B 177.75(17) . . . . ?
C1B C2B C3B C4B 1.1(3) . . . . ?
C2B C3B C4B C5B -0.9(3) . . . . ?
C3B C4B C5B C6B 0.0(4) . . . . ?
C2B C1B C6B C5B -0.4(3) . . . . ?
P1B C1B C6B C5B -178.49(17) . . . . ?
C4B C5B C6B C1B 0.6(3) . . . . ?
C12B C7B C8B C9B 0.7(3) . . . . ?
P1B C7B C8B C9B 176.09(17) . . . . ?
C7B C8B C9B C10B -0.5(3) . . . . ?
C8B C9B C10B C11B -0.1(4) . . . . ?
C9B C10B C11B C12B 0.6(4) . . . . ?
C10B C11B C12B C7B -0.5(4) . . . . ?
C8B C7B C12B C11B -0.2(3) . . . . ?
P1B C7B C12B C11B -175.90(19) . . . . ?
C12B C7B P1B O1B -25.6(2) . . . . ?
C8B C7B P1B O1B 158.91(17) . . . . ?
C12B C7B P1B C13B -151.67(17) . . . . ?
C8B C7B P1B C13B 32.8(2) . . . . ?
C12B C7B P1B C1B 94.89(18) . . . . ?
C8B C7B P1B C1B -80.63(19) . . . . ?
C6B C1B P1B O1B -133.79(18) . . . . ?
C2B C1B P1B O1B 48.06(19) . . . . ?
C6B C1B P1B C13B -7.5(2) . . . . ?
C2B C1B P1B C13B 174.32(16) . . . . ?
C6B C1B P1B C7B 106.20(19) . . . . ?
C2B C1B P1B C7B -71.96(18) . . . . ?
C6C C1C C2C C3C -0.7(3) . . . . ?
P1C C1C C2C C3C -178.20(16) . . . . ?
C1C C2C C3C C4C 1.4(3) . . . . ?
C2C C3C C4C C5C -0.8(3) . . . . ?
C3C C4C C5C C6C -0.5(3) . . . . ?
C2C C1C C6C C5C -0.5(3) . . . . ?
P1C C1C C6C C5C 176.78(17) . . . . ?
C4C C5C C6C C1C 1.1(3) . . . . ?
C12C C7C C8C C9C 0.1(3) . . . . ?
P1C C7C C8C C9C 179.21(17) . . . . ?
C7C C8C C9C C10C -1.3(3) . . . . ?
C8C C9C C10C C11C 1.4(4) . . . . ?
C9C C10C C11C C12C -0.1(4) . . . . ?
C10C C11C C12C C7C -1.1(4) . . . . ?
C8C C7C C12C C11C 1.1(3) . . . . ?
P1C C7C C12C C11C -178.05(18) . . . . ?
C12C C7C P1C O1C -21.2(2) . . . . ?
C8C C7C P1C O1C 159.68(17) . . . . ?
C12C C7C P1C C13C -146.58(17) . . . . ?
C8C C7C P1C C13C 34.3(2) . . . . ?
C12C C7C P1C C1C 99.33(18) . . . . ?
C8C C7C P1C C1C -79.77(19) . . . . ?
C6C C1C P1C O1C -138.90(18) . . . . ?
C2C C1C P1C O1C 38.42(18) . . . . ?
C6C C1C P1C C13C -13.1(2) . . . . ?
C2C C1C P1C C13C 164.20(16) . . . . ?
C6C C1C P1C C7C 100.62(19) . . . . ?
C2C C1C P1C C7C -82.07(18) . . . . ?

_refine_diff_density_max         0.539
_refine_diff_density_min         -0.409
_refine_diff_density_rms         0.060


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: nitromethane'
####################################################################### 
# 
# 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_mono_2mdppo_14tfib_123K
_database_code_depnum_ccdc_archive 'CCDC 1831925'
loop_
_audit_author_name
_audit_author_address
'Filip Topic'
;McGill University
Canada
;
_audit_update_record             
;
2018-03-23 deposited with the CCDC.	2019-10-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_formula_moiety         '2(C13 H13 O P), C6 F4 I2'
_chemical_formula_sum            'C32 H26 F4 I2 O2 P2'
_chemical_formula_weight         834.27

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'
F F 0.0171 0.0103 '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'
O O 0.0106 0.0060 '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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   11.5273(4)
_cell_length_b                   5.88431(18)
_cell_length_c                   23.5890(7)
_cell_angle_alpha                90
_cell_angle_beta                 90.628(3)
_cell_angle_gamma                90
_cell_volume                     1599.95(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    123.0(1)
_cell_measurement_reflns_used    6810
_cell_measurement_theta_min      3.5210
_cell_measurement_theta_max      29.0600

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.732
_exptl_crystal_F_000             812
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.290
_exptl_crystal_size_min          0.148
_exptl_absorpt_coefficient_mu    2.117
_shelx_estimated_absorpt_T_min   0.485
_shelx_estimated_absorpt_T_max   0.745
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.79065
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_diffrn_ambient_temperature      123.0(1)
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at zero, Atlas'
_diffrn_detector                 'CCD plate'
_diffrn_detector_type            Atlas
_diffrn_detector_area_resol_mean 5.1977
_diffrn_reflns_number            12445
_diffrn_reflns_av_unetI/netI     0.0293
_diffrn_reflns_av_R_equivalents  0.0258
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         3.120
_diffrn_reflns_theta_max         29.358
_diffrn_reflns_theta_full        25.250
_diffrn_measured_fraction_theta_max 0.894
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.894
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.894
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             3930
_reflns_number_gt                3528
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2015)'
_computing_publication_material  
'OLEX2 (Dolomanov et al., 2009) & WinGX (Farrugia, 2012)'

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0178P)²+0.3814P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3930
_refine_ls_number_parameters     191
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0273
_refine_ls_R_factor_gt           0.0227
_refine_ls_wR_factor_ref         0.0479
_refine_ls_wR_factor_gt          0.0454
_refine_ls_goodness_of_fit_ref   1.067
_refine_ls_restrained_S_all      1.067
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
I1B I 0.80669(2) 0.35904(2) 0.39003(2) 0.02169(5) Uani 1 1 d . . . . .
P1A P 0.57529(4) 0.05867(8) 0.30504(2) 0.01712(11) Uani 1 1 d . . . . .
F1B F 0.82969(10) 0.7940(2) 0.46892(5) 0.0270(3) Uani 1 1 d . . . . .
C7A C 0.49610(17) -0.0235(3) 0.36724(8) 0.0192(4) Uani 1 1 d . . . . .
O1A O 0.62532(12) 0.2920(2) 0.31090(6) 0.0216(3) Uani 1 1 d . . . . .
C8A C 0.5046(2) -0.2350(4) 0.39304(9) 0.0301(5) Uani 1 1 d . . . . .
H8A H 0.554041 -0.348241 0.377820 0.036 Uiso 1 1 calc R U . . .
C12A C 0.4231(2) 0.1387(4) 0.39031(10) 0.0313(5) Uani 1 1 d . . . . .
H12A H 0.416844 0.284043 0.373038 0.038 Uiso 1 1 calc R U . . .
C6A C 0.3999(2) -0.1409(4) 0.23937(10) 0.0302(5) Uani 1 1 d . . . . .
H6A H 0.402176 -0.262826 0.265749 0.036 Uiso 1 1 calc R U . . .
C1A C 0.47287(17) 0.0450(3) 0.24714(8) 0.0191(4) Uani 1 1 d . . . . .
C4A C 0.3197(2) 0.0291(4) 0.15541(10) 0.0351(5) Uani 1 1 d . . . . .
H4A H 0.267414 0.023346 0.124043 0.042 Uiso 1 1 calc R U . . .
C2B C 0.91329(17) 0.6452(3) 0.48379(8) 0.0199(4) Uani 1 1 d . . . . .
C10A C 0.3683(2) -0.1186(4) 0.46360(10) 0.0372(6) Uani 1 1 d . . . . .
H10A H 0.324757 -0.151416 0.496561 0.045 Uiso 1 1 calc R U . . .
C2A C 0.46759(18) 0.2242(4) 0.20831(8) 0.0250(5) Uani 1 1 d . . . . .
H2A H 0.516680 0.352560 0.213195 0.030 Uiso 1 1 calc R U . . .
C9A C 0.4403(2) -0.2802(4) 0.44121(10) 0.0359(6) Uani 1 1 d . . . . .
H9A H 0.446295 -0.424908 0.458877 0.043 Uiso 1 1 calc R U . . .
C13A C 0.68098(19) -0.1568(3) 0.29254(9) 0.0242(5) Uani 1 1 d . . . . .
H13A H 0.736162 -0.161920 0.324412 0.036 Uiso 1 1 calc R U . . .
H13B H 0.722540 -0.122467 0.257546 0.036 Uiso 1 1 calc R U . . .
H13C H 0.642254 -0.304422 0.288791 0.036 Uiso 1 1 calc R U . . .
C1B C 0.92474(17) 0.4427(3) 0.45462(8) 0.0187(4) Uani 1 1 d . . . . .
C5A C 0.3242(2) -0.1498(4) 0.19371(10) 0.0387(6) Uani 1 1 d . . . . .
H5A H 0.275247 -0.278134 0.188500 0.046 Uiso 1 1 calc R U . . .
C3A C 0.3911(2) 0.2151(4) 0.16277(9) 0.0322(5) Uani 1 1 d . . . . .
H3A H 0.387671 0.337390 0.136505 0.039 Uiso 1 1 calc R U . . .
C11A C 0.3594(2) 0.0908(4) 0.43824(10) 0.0410(6) Uani 1 1 d . . . . .
H11A H 0.309446 0.202898 0.453605 0.049 Uiso 1 1 calc R U . . .
F2B F 0.96976(11) 0.89920(19) 0.55545(5) 0.0276(3) Uani 1 1 d . . . . .
C3B C 0.98626(18) 0.7004(3) 0.52833(8) 0.0197(4) 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
I1B C1B 2.091(2) . ?
P1A O1A 1.4952(14) . ?
P1A C13A 1.785(2) . ?
P1A C1A 1.797(2) . ?
P1A C7A 1.8025(19) . ?
F1B C2B 1.346(2) . ?
C7A C12A 1.387(3) . ?
C7A C8A 1.389(3) . ?
C8A C9A 1.389(3) . ?
C8A H8A 0.9500 . ?
C12A C11A 1.384(3) . ?
C12A H12A 0.9500 . ?
C6A C5A 1.380(3) . ?
C6A C1A 1.391(3) . ?
C6A H6A 0.9500 . ?
C1A C2A 1.398(3) . ?
C4A C3A 1.379(3) . ?
C4A C5A 1.388(3) . ?
C4A H4A 0.9500 . ?
C2B C3B 1.378(3) . ?
C2B C1B 1.383(3) . ?
C10A C9A 1.372(3) . ?
C10A C11A 1.373(3) . ?
C10A H10A 0.9500 . ?
C2A C3A 1.383(3) . ?
C2A H2A 0.9500 . ?
C9A H9A 0.9500 . ?
C13A H13A 0.9800 . ?
C13A H13B 0.9800 . ?
C13A H13C 0.9800 . ?
C1B C3B 1.384(3) 3_766 ?
C5A H5A 0.9500 . ?
C3A H3A 0.9500 . ?
C11A H11A 0.9500 . ?
F2B C3B 1.348(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
O1A P1A C13A 113.85(9) . . ?
O1A P1A C1A 111.15(9) . . ?
C13A P1A C1A 106.65(10) . . ?
O1A P1A C7A 111.67(8) . . ?
C13A P1A C7A 107.25(9) . . ?
C1A P1A C7A 105.80(9) . . ?
C12A C7A C8A 118.99(18) . . ?
C12A C7A P1A 116.72(15) . . ?
C8A C7A P1A 124.29(15) . . ?
C7A C8A C9A 119.7(2) . . ?
C7A C8A H8A 120.2 . . ?
C9A C8A H8A 120.2 . . ?
C11A C12A C7A 120.7(2) . . ?
C11A C12A H12A 119.7 . . ?
C7A C12A H12A 119.7 . . ?
C5A C6A C1A 120.6(2) . . ?
C5A C6A H6A 119.7 . . ?
C1A C6A H6A 119.7 . . ?
C6A C1A C2A 119.02(19) . . ?
C6A C1A P1A 121.78(16) . . ?
C2A C1A P1A 119.19(16) . . ?
C3A C4A C5A 120.1(2) . . ?
C3A C4A H4A 119.9 . . ?
C5A C4A H4A 119.9 . . ?
F1B C2B C3B 118.34(17) . . ?
F1B C2B C1B 120.20(18) . . ?
C3B C2B C1B 121.46(18) . . ?
C9A C10A C11A 119.8(2) . . ?
C9A C10A H10A 120.1 . . ?
C11A C10A H10A 120.1 . . ?
C3A C2A C1A 120.2(2) . . ?
C3A C2A H2A 119.9 . . ?
C1A C2A H2A 119.9 . . ?
C10A C9A C8A 120.8(2) . . ?
C10A C9A H9A 119.6 . . ?
C8A C9A H9A 119.6 . . ?
P1A C13A H13A 109.5 . . ?
P1A C13A H13B 109.5 . . ?
H13A C13A H13B 109.5 . . ?
P1A C13A H13C 109.5 . . ?
H13A C13A H13C 109.5 . . ?
H13B C13A H13C 109.5 . . ?
C2B C1B C3B 117.01(18) . 3_766 ?
C2B C1B I1B 120.04(15) . . ?
C3B C1B I1B 122.91(14) 3_766 . ?
C6A C5A C4A 119.9(2) . . ?
C6A C5A H5A 120.1 . . ?
C4A C5A H5A 120.1 . . ?
C4A C3A C2A 120.2(2) . . ?
C4A C3A H3A 119.9 . . ?
C2A C3A H3A 119.9 . . ?
C10A C11A C12A 120.0(2) . . ?
C10A C11A H11A 120.0 . . ?
C12A C11A H11A 120.0 . . ?
F2B C3B C2B 118.60(17) . . ?
F2B C3B C1B 119.89(18) . 3_766 ?
C2B C3B C1B 121.52(17) . 3_766 ?

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
O1A P1A C7A C12A 43.8(2) . . . . ?
C13A P1A C7A C12A 169.19(17) . . . . ?
C1A P1A C7A C12A -77.26(18) . . . . ?
O1A P1A C7A C8A -135.71(18) . . . . ?
C13A P1A C7A C8A -10.3(2) . . . . ?
C1A P1A C7A C8A 103.23(19) . . . . ?
C12A C7A C8A C9A -0.1(3) . . . . ?
P1A C7A C8A C9A 179.45(18) . . . . ?
C8A C7A C12A C11A -0.1(4) . . . . ?
P1A C7A C12A C11A -179.7(2) . . . . ?
C5A C6A C1A C2A 0.7(3) . . . . ?
C5A C6A C1A P1A -178.26(18) . . . . ?
O1A P1A C1A C6A -168.38(16) . . . . ?
C13A P1A C1A C6A 66.99(19) . . . . ?
C7A P1A C1A C6A -46.98(19) . . . . ?
O1A P1A C1A C2A 12.67(18) . . . . ?
C13A P1A C1A C2A -111.96(17) . . . . ?
C7A P1A C1A C2A 134.07(16) . . . . ?
C6A C1A C2A C3A -0.3(3) . . . . ?
P1A C1A C2A C3A 178.68(16) . . . . ?
C11A C10A C9A C8A 0.0(4) . . . . ?
C7A C8A C9A C10A 0.1(4) . . . . ?
F1B C2B C1B C3B 179.00(16) . . . 3_766 ?
C3B C2B C1B C3B -0.9(3) . . . 3_766 ?
F1B C2B C1B I1B -3.3(2) . . . . ?
C3B C2B C1B I1B 176.88(14) . . . . ?
C1A C6A C5A C4A -0.7(4) . . . . ?
C3A C4A C5A C6A 0.3(4) . . . . ?
C5A C4A C3A C2A 0.1(4) . . . . ?
C1A C2A C3A C4A -0.1(3) . . . . ?
C9A C10A C11A C12A -0.2(4) . . . . ?
C7A C12A C11A C10A 0.3(4) . . . . ?
F1B C2B C3B F2B 0.9(3) . . . . ?
C1B C2B C3B F2B -179.26(17) . . . . ?
F1B C2B C3B C1B -178.97(17) . . . 3_766 ?
C1B C2B C3B C1B 0.9(3) . . . 3_766 ?

_refine_diff_density_max         0.428
_refine_diff_density_min         -0.620
_refine_diff_density_rms         0.078


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetonitrile'
####################################################################### 
# 
# 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_tric_2mdppo_14tfib_253K
_database_code_depnum_ccdc_archive 'CCDC 1831927'
loop_
_audit_author_name
_audit_author_address
'Filip Topic'
;McGill University
Canada
;
_audit_update_record             
;
2018-03-23 deposited with the CCDC.	2019-10-25 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2017/1
_shelx_SHELXL_version_number     2017/1
_chemical_formula_moiety         '2(C13 H13 O P), C6 F4 I2'
_chemical_formula_sum            'C32 H26 F4 I2 O2 P2'
_chemical_formula_weight         834.27

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'
F F 0.0171 0.0103 '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'
O O 0.0106 0.0060 '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'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.04730(10)
_cell_length_b                   12.0007(2)
_cell_length_c                   12.56410(10)
_cell_angle_alpha                116.0359(6)
_cell_angle_beta                 100.5276(7)
_cell_angle_gamma                94.7799(7)
_cell_volume                     791.56(2)
_cell_formula_units_Z            1
_cell_measurement_temperature    253.0(1)
_cell_measurement_reflns_used    3436
_cell_measurement_theta_min      0.407
_cell_measurement_theta_max      27.103

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.750
_exptl_crystal_F_000             406
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    2.139
_shelx_estimated_absorpt_T_min   0.566
_shelx_estimated_absorpt_T_max   0.815
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6333
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   'SADABS 2008 (Sheldrick, 1996)'

_diffrn_ambient_temperature      253.0(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  'horizonally mounted graphite crystal'
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_device       '95mm CCD camera on κ-goniostat'
_diffrn_measurement_method       'φ scans + ω scans'
_diffrn_detector_area_resol_mean 9
_diffrn_reflns_number            19024
_diffrn_reflns_av_unetI/netI     0.0189
_diffrn_reflns_av_R_equivalents  0.0253
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.237
_diffrn_reflns_theta_max         27.519
_diffrn_reflns_theta_full        25.250
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.981
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.981
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             3572
_reflns_number_gt                3360
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'Collect (Bruker AXS BV, 1997-2004)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor, 1997)'
_computing_data_reduction        
'HKL Denzo and Scalepack (Otwinowski & Minor, 1997)'
_computing_structure_solution    'SHELXT-2014/5 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2017/1 (Sheldrick, 2015)'
_computing_publication_material  
'OLEX2 (Dolomanov et al., 2009) & WinGX publication routines (Farrugia, 2012)'

_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0178P)²+0.4440P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     iterative
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2017/1 (Sheldrick 2017)'
_refine_ls_extinction_coef       0.0040(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3572
_refine_ls_number_parameters     192
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0222
_refine_ls_R_factor_gt           0.0202
_refine_ls_wR_factor_ref         0.0482
_refine_ls_wR_factor_gt          0.0474
_refine_ls_goodness_of_fit_ref   1.056
_refine_ls_restrained_S_all      1.056
_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_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1B C 0.5096(4) 0.12761(19) 0.08242(19) 0.0416(4) Uani 1 1 d . . . . .
C2B C 0.6936(4) 0.0687(2) 0.0888(2) 0.0471(5) Uani 1 1 d . . . . .
C3B C 0.6835(4) -0.0557(2) 0.0090(2) 0.0482(5) Uani 1 1 d . . . . .
F1B F 0.8875(3) 0.13326(14) 0.17580(15) 0.0760(5) Uani 1 1 d . . . . .
F2B F 0.8703(3) -0.10729(14) 0.02138(16) 0.0762(5) Uani 1 1 d . . . . .
I1B I 0.52804(2) 0.31644(2) 0.20621(2) 0.04339(7) Uani 1 1 d . . . . .
C1A C 0.4274(3) 0.79034(19) 0.51198(18) 0.0390(4) Uani 1 1 d . . . . .
C2A C 0.6404(4) 0.8380(2) 0.5901(2) 0.0587(6) Uani 1 1 d . . . . .
H2A H 0.754186 0.789349 0.577370 0.070 Uiso 1 1 calc R U . . .
C3A C 0.6878(6) 0.9581(3) 0.6882(3) 0.0776(9) Uani 1 1 d . . . . .
H3A H 0.832522 0.988798 0.741406 0.093 Uiso 1 1 calc R U . . .
C4A C 0.5261(6) 1.0312(2) 0.7074(2) 0.0705(8) Uani 1 1 d . . . . .
H4A H 0.560017 1.112211 0.772625 0.085 Uiso 1 1 calc R U . . .
C5A C 0.3154(6) 0.9858(3) 0.6312(3) 0.0951(12) Uani 1 1 d . . . . .
H5A H 0.203887 1.035959 0.643981 0.114 Uiso 1 1 calc R U . . .
C6A C 0.2635(5) 0.8649(3) 0.5339(3) 0.0850(11) Uani 1 1 d . . . . .
H6A H 0.116527 0.834005 0.483137 0.102 Uiso 1 1 calc R U . . .
C7A C 0.2496(3) 0.64208(17) 0.25008(17) 0.0351(4) Uani 1 1 d . . . . .
C8A C 0.0369(4) 0.6753(2) 0.2273(2) 0.0461(5) Uani 1 1 d . . . . .
H8A H -0.053930 0.689481 0.282644 0.055 Uiso 1 1 calc R U . . .
C9A C -0.0393(4) 0.6874(2) 0.1228(2) 0.0519(5) Uani 1 1 d . . . . .
H9A H -0.179577 0.711601 0.109191 0.062 Uiso 1 1 calc R U . . .
C10A C 0.0916(4) 0.6636(2) 0.0385(2) 0.0479(5) Uani 1 1 d . . . . .
H10A H 0.039975 0.672146 -0.031439 0.058 Uiso 1 1 calc R U . . .
C11A C 0.2992(4) 0.6273(2) 0.05860(19) 0.0454(5) Uani 1 1 d . . . . .
H11A H 0.386102 0.609526 0.001165 0.054 Uiso 1 1 calc R U . . .
C12A C 0.3787(4) 0.61710(18) 0.16423(18) 0.0395(4) Uani 1 1 d . . . . .
H12A H 0.519604 0.593368 0.177565 0.047 Uiso 1 1 calc R U . . .
C13A C 0.1523(4) 0.5425(2) 0.4117(2) 0.0481(5) Uani 1 1 d . . . . .
H13A H 0.210376 0.535455 0.484431 0.072 Uiso 1 1 calc R U . . .
H13B H 0.106215 0.459744 0.343017 0.072 Uiso 1 1 calc R U . . .
H13C H 0.022947 0.584077 0.420580 0.072 Uiso 1 1 calc R U . . .
O1A O 0.5839(2) 0.57775(14) 0.37759(13) 0.0433(3) Uani 1 1 d . . . . .
P1A P 0.37084(8) 0.63217(5) 0.38737(4) 0.03362(11) 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
C1B C2B 1.375(3) . ?
C1B C3B 1.378(3) 2_655 ?
C1B I1B 2.090(2) . ?
C2B F1B 1.344(2) . ?
C2B C3B 1.374(3) . ?
C3B F2B 1.349(2) . ?
C1A C2A 1.368(3) . ?
C1A C6A 1.375(3) . ?
C1A P1A 1.805(2) . ?
C2A C3A 1.386(4) . ?
C2A H2A 0.9300 . ?
C3A C4A 1.351(4) . ?
C3A H3A 0.9300 . ?
C4A C5A 1.348(5) . ?
C4A H4A 0.9300 . ?
C5A C6A 1.387(4) . ?
C5A H5A 0.9300 . ?
C6A H6A 0.9300 . ?
C7A C12A 1.388(3) . ?
C7A C8A 1.395(3) . ?
C7A P1A 1.8054(19) . ?
C8A C9A 1.384(3) . ?
C8A H8A 0.9300 . ?
C9A C10A 1.381(3) . ?
C9A H9A 0.9300 . ?
C10A C11A 1.379(3) . ?
C10A H10A 0.9300 . ?
C11A C12A 1.388(3) . ?
C11A H11A 0.9300 . ?
C12A H12A 0.9300 . ?
C13A P1A 1.788(2) . ?
C13A H13A 0.9600 . ?
C13A H13B 0.9600 . ?
C13A H13C 0.9600 . ?
O1A P1A 1.4932(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
C2B C1B C3B 116.49(19) . 2_655 ?
C2B C1B I1B 120.79(15) . . ?
C3B C1B I1B 122.72(15) 2_655 . ?
F1B C2B C3B 118.82(19) . . ?
F1B C2B C1B 119.64(19) . . ?
C3B C2B C1B 121.53(19) . . ?
F2B C3B C2B 118.16(19) . . ?
F2B C3B C1B 119.86(19) . 2_655 ?
C2B C3B C1B 121.98(19) . 2_655 ?
C2A C1A C6A 118.1(2) . . ?
C2A C1A P1A 119.13(17) . . ?
C6A C1A P1A 122.79(18) . . ?
C1A C2A C3A 120.5(3) . . ?
C1A C2A H2A 119.7 . . ?
C3A C2A H2A 119.7 . . ?
C4A C3A C2A 120.8(3) . . ?
C4A C3A H3A 119.6 . . ?
C2A C3A H3A 119.6 . . ?
C5A C4A C3A 119.5(3) . . ?
C5A C4A H4A 120.2 . . ?
C3A C4A H4A 120.2 . . ?
C4A C5A C6A 120.5(3) . . ?
C4A C5A H5A 119.7 . . ?
C6A C5A H5A 119.7 . . ?
C1A C6A C5A 120.6(3) . . ?
C1A C6A H6A 119.7 . . ?
C5A C6A H6A 119.7 . . ?
C12A C7A C8A 118.89(19) . . ?
C12A C7A P1A 117.52(15) . . ?
C8A C7A P1A 123.59(15) . . ?
C9A C8A C7A 120.2(2) . . ?
C9A C8A H8A 119.9 . . ?
C7A C8A H8A 119.9 . . ?
C10A C9A C8A 120.4(2) . . ?
C10A C9A H9A 119.8 . . ?
C8A C9A H9A 119.8 . . ?
C11A C10A C9A 119.7(2) . . ?
C11A C10A H10A 120.1 . . ?
C9A C10A H10A 120.1 . . ?
C10A C11A C12A 120.2(2) . . ?
C10A C11A H11A 119.9 . . ?
C12A C11A H11A 119.9 . . ?
C7A C12A C11A 120.47(19) . . ?
C7A C12A H12A 119.8 . . ?
C11A C12A H12A 119.8 . . ?
P1A C13A H13A 109.5 . . ?
P1A C13A H13B 109.5 . . ?
H13A C13A H13B 109.5 . . ?
P1A C13A H13C 109.5 . . ?
H13A C13A H13C 109.5 . . ?
H13B C13A H13C 109.5 . . ?
O1A P1A C13A 113.53(10) . . ?
O1A P1A C1A 111.46(9) . . ?
C13A P1A C1A 106.81(11) . . ?
O1A P1A C7A 110.89(9) . . ?
C13A P1A C7A 107.02(10) . . ?
C1A P1A C7A 106.76(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
C3B C1B C2B F1B -179.9(2) 2_655 . . . ?
I1B C1B C2B F1B 0.1(3) . . . . ?
C3B C1B C2B C3B -0.8(4) 2_655 . . . ?
I1B C1B C2B C3B 179.27(19) . . . . ?
F1B C2B C3B F2B -0.4(4) . . . . ?
C1B C2B C3B F2B -179.5(2) . . . . ?
F1B C2B C3B C1B 180.0(2) . . . 2_655 ?
C1B C2B C3B C1B 0.9(4) . . . 2_655 ?
C6A C1A C2A C3A -0.1(4) . . . . ?
P1A C1A C2A C3A -178.6(2) . . . . ?
C1A C2A C3A C4A -1.1(5) . . . . ?
C2A C3A C4A C5A 1.0(5) . . . . ?
C3A C4A C5A C6A 0.2(6) . . . . ?
C2A C1A C6A C5A 1.3(5) . . . . ?
P1A C1A C6A C5A 179.8(3) . . . . ?
C4A C5A C6A C1A -1.4(6) . . . . ?
C12A C7A C8A C9A -2.2(3) . . . . ?
P1A C7A C8A C9A 176.59(18) . . . . ?
C7A C8A C9A C10A 1.6(4) . . . . ?
C8A C9A C10A C11A 0.2(4) . . . . ?
C9A C10A C11A C12A -1.4(3) . . . . ?
C8A C7A C12A C11A 1.1(3) . . . . ?
P1A C7A C12A C11A -177.77(16) . . . . ?
C10A C11A C12A C7A 0.7(3) . . . . ?
C2A C1A P1A O1A -7.1(2) . . . . ?
C6A C1A P1A O1A 174.4(2) . . . . ?
C2A C1A P1A C13A 117.4(2) . . . . ?
C6A C1A P1A C13A -61.0(3) . . . . ?
C2A C1A P1A C7A -128.4(2) . . . . ?
C6A C1A P1A C7A 53.2(3) . . . . ?
C12A C7A P1A O1A -8.84(18) . . . . ?
C8A C7A P1A O1A 172.30(17) . . . . ?
C12A C7A P1A C13A -133.16(16) . . . . ?
C8A C7A P1A C13A 48.0(2) . . . . ?
C12A C7A P1A C1A 112.76(16) . . . . ?
C8A C7A P1A C1A -66.10(19) . . . . ?

_refine_diff_density_max         0.285
_refine_diff_density_min         -0.363
_refine_diff_density_rms         0.051


_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent'
_chemical_compound_source        isobutanol
