# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_ax2022_Tip2P2Br2_cmpd_RS_1
_database_code_depnum_ccdc_archive 'CCDC 2098825'
loop_
_audit_author_name
_audit_author_address
'Christian Hering-Junghans'
;Leibniz Institute for Catalysis Rostock
Germany
;
_audit_update_record             
;
2021-07-23 deposited with the CCDC.	2021-09-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7

#==============================================================================

# CHEMICAL DATA

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H46 Br2 P2'
_chemical_formula_sum            'C30 H46 Br2 P2'
_chemical_formula_weight         628.43

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'
Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

#==============================================================================

# CRYSTAL DATA

_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, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   9.0324(4)
_cell_length_b                   16.1088(8)
_cell_length_c                   21.3757(11)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3110.2(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9973
_cell_measurement_theta_min      2.53
_cell_measurement_theta_max      30.56

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.342
_exptl_crystal_F_000             1304
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.270
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    2.726
_shelx_estimated_absorpt_T_min   0.526
_shelx_estimated_absorpt_T_max   0.754
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.526
_exptl_absorpt_correction_T_max  0.754
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_absorpt_special_details   ?

#==============================================================================

# EXPERIMENTAL DATA

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            39293
_diffrn_reflns_av_unetI/netI     0.0248
_diffrn_reflns_av_R_equivalents  0.0404
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         1.905
_diffrn_reflns_theta_max         29.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4538
_reflns_number_gt                3482
_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       'APEX2 (Bruker, 2014)'
_computing_cell_refinement       'SAINT (Bruker, 2013)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP-3v2.01 (Farrugia, 1997)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'

#==============================================================================

# REFINEMENT DATA 

_refine_special_details          
;
 All H atoms 
 were positioned geometrically and refined using a riding model, with C---H = 
 0.98 (methyl groups), 0.99Å (methylene groups), 1.00Å (methine groups) or 
 0.95 Å (aryl CH) and with Uiso(H) = 1.5 times Ueq(C) 
 (methyl groups) or with Uiso(H) = 1.2 times Ueq(C) 
 (methylene  groups, aryl CH, methine groups). Torsion angles of all methyl 
 groups were allowed to refine.
 
 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 > 2σ(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     
'w=1/[σ²(Fo²)+(0.0391P)²+0.7327P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4538
_refine_ls_number_parameters     160
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0453
_refine_ls_R_factor_gt           0.0293
_refine_ls_wR_factor_ref         0.0757
_refine_ls_wR_factor_gt          0.0697
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_restrained_S_all      1.020
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

#==============================================================================

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

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
P1 P 0.56599(4) 0.55296(2) 0.51938(2) 0.01794(9) Uani 1 1 d . . . . .
Br1 Br 0.78858(2) 0.50124(2) 0.49101(2) 0.02679(6) Uani 1 1 d . . . . .
C1 C 0.52508(16) 0.63629(9) 0.46356(7) 0.0165(3) Uani 1 1 d . . . . .
C2 C 0.51988(16) 0.62984(10) 0.39731(7) 0.0184(3) Uani 1 1 d . . . . .
C3 C 0.47151(17) 0.69824(10) 0.36289(7) 0.0211(3) Uani 1 1 d . . . . .
H3 H 0.4690 0.6942 0.3186 0.025 Uiso 1 1 calc R U . . .
C4 C 0.42685(17) 0.77197(9) 0.39070(7) 0.0201(3) Uani 1 1 d . . . . .
C5 C 0.43790(17) 0.77802(9) 0.45546(7) 0.0198(3) Uani 1 1 d . . . . .
H5 H 0.4101 0.8286 0.4751 0.024 Uiso 1 1 calc R U . . .
C6 C 0.48809(15) 0.71289(10) 0.49268(7) 0.0171(3) Uani 1 1 d . . . . .
C7 C 0.56722(19) 0.55386(10) 0.36049(7) 0.0225(3) Uani 1 1 d . . . . .
H7 H 0.5978 0.5103 0.3912 0.027 Uiso 1 1 calc R U . . .
C8 C 0.7009(2) 0.57262(12) 0.31883(9) 0.0330(4) Uani 1 1 d . . . . .
H8A H 0.7307 0.5220 0.2967 0.049 Uiso 1 1 calc R U . . .
H8B H 0.7832 0.5923 0.3448 0.049 Uiso 1 1 calc R U . . .
H8C H 0.6743 0.6155 0.2883 0.049 Uiso 1 1 calc R U . . .
C9 C 0.4393(3) 0.51858(12) 0.32181(9) 0.0347(4) Uani 1 1 d . . . . .
H9A H 0.3528 0.5104 0.3488 0.052 Uiso 1 1 calc R U . . .
H9B H 0.4689 0.4652 0.3037 0.052 Uiso 1 1 calc R U . . .
H9C H 0.4142 0.5575 0.2882 0.052 Uiso 1 1 calc R U . . .
C10 C 0.37305(19) 0.84612(10) 0.35313(8) 0.0237(3) Uani 1 1 d . . . . .
H10 H 0.2932 0.8735 0.3782 0.028 Uiso 1 1 calc R U . . .
C11 C 0.3065(3) 0.82371(14) 0.29019(10) 0.0457(5) Uani 1 1 d . . . . .
H11A H 0.3835 0.8003 0.2631 0.069 Uiso 1 1 calc R U . . .
H11B H 0.2653 0.8737 0.2706 0.069 Uiso 1 1 calc R U . . .
H11C H 0.2276 0.7827 0.2962 0.069 Uiso 1 1 calc R U . . .
C12 C 0.4964(2) 0.90922(13) 0.34524(10) 0.0383(5) Uani 1 1 d . . . . .
H12A H 0.5348 0.9250 0.3864 0.057 Uiso 1 1 calc R U . . .
H12B H 0.4577 0.9586 0.3240 0.057 Uiso 1 1 calc R U . . .
H12C H 0.5763 0.8849 0.3202 0.057 Uiso 1 1 calc R U . . .
C13 C 0.49776(17) 0.72692(10) 0.56340(7) 0.0197(3) Uani 1 1 d . . . . .
H13 H 0.5689 0.6851 0.5805 0.024 Uiso 1 1 calc R U . . .
C14 C 0.3483(2) 0.71145(12) 0.59455(8) 0.0308(4) Uani 1 1 d . . . . .
H14A H 0.2746 0.7497 0.5772 0.046 Uiso 1 1 calc R U . . .
H14B H 0.3571 0.7206 0.6397 0.046 Uiso 1 1 calc R U . . .
H14C H 0.3172 0.6541 0.5868 0.046 Uiso 1 1 calc R U . . .
C15 C 0.5573(2) 0.81317(10) 0.58016(8) 0.0279(4) Uani 1 1 d . . . . .
H15A H 0.4853 0.8555 0.5676 0.042 Uiso 1 1 calc R U . . .
H15B H 0.6510 0.8227 0.5582 0.042 Uiso 1 1 calc R U . . .
H15C H 0.5739 0.8165 0.6254 0.042 Uiso 1 1 calc R U . . .


#==============================================================================

# MOLECULAR GEOMETRY

_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 C1 1.8337(15) . ?
P1 P1 2.2402(8) 5_666 ?
P1 Br1 2.2592(4) . ?
C1 C2 1.421(2) . ?
C1 C6 1.422(2) . ?
C2 C3 1.395(2) . ?
C2 C7 1.517(2) . ?
C3 C4 1.388(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.391(2) . ?
C4 C10 1.519(2) . ?
C5 C6 1.393(2) . ?
C5 H5 0.9500 . ?
C6 C13 1.531(2) . ?
C7 C8 1.530(2) . ?
C7 C9 1.530(3) . ?
C7 H7 1.0000 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.517(2) . ?
C10 C12 1.517(2) . ?
C10 H10 1.0000 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.525(2) . ?
C13 C15 1.532(2) . ?
C13 H13 1.0000 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 P1 P1 102.10(5) . 5_666 ?
C1 P1 Br1 105.94(5) . . ?
P1 P1 Br1 95.36(2) 5_666 . ?
C2 C1 C6 119.48(13) . . ?
C2 C1 P1 126.99(12) . . ?
C6 C1 P1 113.44(11) . . ?
C3 C2 C1 118.57(14) . . ?
C3 C2 C7 116.87(13) . . ?
C1 C2 C7 124.54(14) . . ?
C4 C3 C2 122.75(14) . . ?
C4 C3 H3 118.6 . . ?
C2 C3 H3 118.6 . . ?
C3 C4 C5 117.72(14) . . ?
C3 C4 C10 122.63(14) . . ?
C5 C4 C10 119.60(14) . . ?
C4 C5 C6 122.63(14) . . ?
C4 C5 H5 118.7 . . ?
C6 C5 H5 118.7 . . ?
C5 C6 C1 118.69(13) . . ?
C5 C6 C13 118.14(14) . . ?
C1 C6 C13 123.17(14) . . ?
C2 C7 C8 111.41(13) . . ?
C2 C7 C9 111.54(15) . . ?
C8 C7 C9 110.77(15) . . ?
C2 C7 H7 107.6 . . ?
C8 C7 H7 107.6 . . ?
C9 C7 H7 107.6 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 C12 110.60(16) . . ?
C11 C10 C4 114.11(14) . . ?
C12 C10 C4 110.52(14) . . ?
C11 C10 H10 107.1 . . ?
C12 C10 H10 107.1 . . ?
C4 C10 H10 107.1 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C14 C13 C6 110.87(13) . . ?
C14 C13 C15 110.91(14) . . ?
C6 C13 C15 112.62(13) . . ?
C14 C13 H13 107.4 . . ?
C6 C13 H13 107.4 . . ?
C15 C13 H13 107.4 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C13 C15 H15A 109.5 . . ?
C13 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C13 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
P1 P1 C1 C2 -43.33(14) 5_666 . . . ?
Br1 P1 C1 C2 55.92(14) . . . . ?
P1 P1 C1 C6 133.23(10) 5_666 . . . ?
Br1 P1 C1 C6 -127.53(10) . . . . ?
C6 C1 C2 C3 -3.0(2) . . . . ?
P1 C1 C2 C3 173.35(11) . . . . ?
C6 C1 C2 C7 175.36(14) . . . . ?
P1 C1 C2 C7 -8.3(2) . . . . ?
C1 C2 C3 C4 -0.7(2) . . . . ?
C7 C2 C3 C4 -179.19(15) . . . . ?
C2 C3 C4 C5 3.0(2) . . . . ?
C2 C3 C4 C10 -179.49(15) . . . . ?
C3 C4 C5 C6 -1.6(2) . . . . ?
C10 C4 C5 C6 -179.18(14) . . . . ?
C4 C5 C6 C1 -2.0(2) . . . . ?
C4 C5 C6 C13 179.16(14) . . . . ?
C2 C1 C6 C5 4.3(2) . . . . ?
P1 C1 C6 C5 -172.51(11) . . . . ?
C2 C1 C6 C13 -176.94(13) . . . . ?
P1 C1 C6 C13 6.22(18) . . . . ?
C3 C2 C7 C8 62.71(19) . . . . ?
C1 C2 C7 C8 -115.70(17) . . . . ?
C3 C2 C7 C9 -61.65(18) . . . . ?
C1 C2 C7 C9 119.95(17) . . . . ?
C3 C4 C10 C11 26.4(2) . . . . ?
C5 C4 C10 C11 -156.10(17) . . . . ?
C3 C4 C10 C12 -98.98(19) . . . . ?
C5 C4 C10 C12 78.5(2) . . . . ?
C5 C6 C13 C14 84.17(18) . . . . ?
C1 C6 C13 C14 -94.56(17) . . . . ?
C5 C6 C13 C15 -40.77(19) . . . . ?
C1 C6 C13 C15 140.49(15) . . . . ?

_refine_diff_density_max         0.428
_refine_diff_density_min         -0.253
_refine_diff_density_rms         0.066

####################################################################### 
# 
# 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_ks1512_Dip2P2_cmpd_2
_database_code_depnum_ccdc_archive 'CCDC 2098827'
loop_
_audit_author_name
_audit_author_address
'Christian Hering-Junghans'
;Leibniz Institute for Catalysis Rostock
Germany
;
_audit_update_record             
;
2021-07-23 deposited with the CCDC.	2021-09-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7

#==============================================================================

# CHEMICAL DATA

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C24 H34 P2'
_chemical_formula_sum            'C24 H34 P2'
_chemical_formula_weight         384.45

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'

#==============================================================================

# CRYSTAL DATA

_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                   6.1450(12)
_cell_length_b                   8.4640(17)
_cell_length_c                   21.620(4)
_cell_angle_alpha                90
_cell_angle_beta                 92.81(3)
_cell_angle_gamma                90
_cell_volume                     1123.1(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    10730
_cell_measurement_theta_min      1.80
_cell_measurement_theta_max      29.97

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.137
_exptl_crystal_F_000             416
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.200
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.199
_shelx_estimated_absorpt_T_min   0.946
_shelx_estimated_absorpt_T_max   0.971
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.946
_exptl_absorpt_correction_T_max  0.971
_exptl_absorpt_process_details   'LANA (Stoe & Cie, 2012)'
_exptl_absorpt_special_details   ?

#==============================================================================

# EXPERIMENTAL DATA

_diffrn_ambient_temperature      150(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  'STOE-IPDS II'
_diffrn_measurement_method       'omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21095
_diffrn_reflns_av_unetI/netI     0.0201
_diffrn_reflns_av_R_equivalents  0.0276
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_theta_min         1.886
_diffrn_reflns_theta_max         29.130
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             3038
_reflns_number_gt                2480
_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       'APEX2 (Bruker, 2014)'
_computing_cell_refinement       'SAINT (Bruker, 2013)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP-3v2.01 (Farrugia, 1997)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'

#==============================================================================

# REFINEMENT DATA 

_refine_special_details          
;
 All H atoms 
 were positioned geometrically and refined using a riding model, with C---H = 
 0.98 (methyl groups), 0.99Å (methylene groups), 1.00Å (methine groups) or 
 0.95 Å (aryl CH) and with Uiso(H) = 1.5 times Ueq(C) 
 (methyl groups) or with Uiso(H) = 1.2 times Ueq(C) 
 (methylene  groups, aryl CH, methine groups). Torsion angles of all methyl 
 groups were allowed to refine.
 
 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 > 2σ(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     
'w=1/[σ²(Fo²)+(0.0567P)²+0.0291P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3038
_refine_ls_number_parameters     122
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0382
_refine_ls_R_factor_gt           0.0305
_refine_ls_wR_factor_ref         0.0865
_refine_ls_wR_factor_gt          0.0843
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_restrained_S_all      1.028
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

#==============================================================================

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

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
P1 P 0.63124(4) 0.55285(3) 0.52148(2) 0.02337(9) Uani 1 1 d . . . . .
C1 C 0.60490(16) 0.47640(12) 0.60079(4) 0.0224(2) Uani 1 1 d . . . . .
C2 C 0.71247(17) 0.33610(13) 0.61912(5) 0.0245(2) Uani 1 1 d . . . . .
C3 C 0.68739(19) 0.27934(14) 0.67889(5) 0.0304(2) Uani 1 1 d . . . . .
H3 H 0.7558 0.1859 0.6914 0.036 Uiso 1 1 calc R U . . .
C4 C 0.5619(2) 0.36047(15) 0.71979(5) 0.0330(3) Uani 1 1 d . . . . .
H4 H 0.5438 0.3200 0.7592 0.040 Uiso 1 1 calc R U . . .
C5 C 0.46376(19) 0.50102(15) 0.70232(5) 0.0304(2) Uani 1 1 d . . . . .
H5 H 0.3824 0.5557 0.7305 0.036 Uiso 1 1 calc R U . . .
C6 C 0.48456(17) 0.56246(13) 0.64306(5) 0.0246(2) Uani 1 1 d . . . . .
C7 C 0.85186(18) 0.24494(13) 0.57525(5) 0.0277(2) Uani 1 1 d . . . . .
H7 H 0.8814 0.3153 0.5407 0.033 Uiso 1 1 calc R U . . .
C8 C 0.7284(2) 0.10224(16) 0.54853(6) 0.0388(3) Uani 1 1 d . . . . .
H8A H 0.6984 0.0302 0.5813 0.058 Uiso 1 1 calc R U . . .
H8B H 0.8152 0.0502 0.5190 0.058 Uiso 1 1 calc R U . . .
H8C H 0.5937 0.1365 0.5285 0.058 Uiso 1 1 calc R U . . .
C9 C 1.0715(2) 0.19605(16) 0.60558(6) 0.0372(3) Uani 1 1 d . . . . .
H9A H 1.1450 0.2876 0.6224 0.056 Uiso 1 1 calc R U . . .
H9B H 1.1590 0.1480 0.5752 0.056 Uiso 1 1 calc R U . . .
H9C H 1.0484 0.1218 0.6382 0.056 Uiso 1 1 calc R U . . .
C10 C 0.37503(18) 0.71820(13) 0.62575(5) 0.0281(2) Uani 1 1 d . . . . .
H10 H 0.4333 0.7533 0.5867 0.034 Uiso 1 1 calc R U . . .
C11 C 0.1294(2) 0.69497(16) 0.61434(6) 0.0380(3) Uani 1 1 d . . . . .
H11A H 0.1029 0.6231 0.5805 0.057 Uiso 1 1 calc R U . . .
H11B H 0.0621 0.7948 0.6045 0.057 Uiso 1 1 calc R U . . .
H11C H 0.0690 0.6524 0.6509 0.057 Uiso 1 1 calc R U . . .
C12 C 0.4262(2) 0.84694(15) 0.67393(6) 0.0352(3) Uani 1 1 d . . . . .
H12A H 0.3645 0.8185 0.7123 0.053 Uiso 1 1 calc R U . . .
H12B H 0.3650 0.9454 0.6595 0.053 Uiso 1 1 calc R U . . .
H12C H 0.5812 0.8578 0.6802 0.053 Uiso 1 1 calc R U . . .


#==============================================================================

# MOLECULAR GEOMETRY

_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 C1 1.8471(10) . ?
P1 P1 2.0293(7) 3_666 ?
C1 C2 1.4066(15) . ?
C1 C6 1.4068(14) . ?
C2 C3 1.3942(15) . ?
C2 C7 1.5193(15) . ?
C3 C4 1.3836(17) . ?
C3 H3 0.9300 . ?
C4 C5 1.3781(17) . ?
C4 H4 0.9300 . ?
C5 C6 1.3945(15) . ?
C5 H5 0.9300 . ?
C6 C10 1.5185(15) . ?
C7 C8 1.5250(17) . ?
C7 C9 1.5284(16) . ?
C7 H7 0.9800 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C12 1.5294(16) . ?
C10 C11 1.5305(16) . ?
C10 H10 0.9800 . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
C12 H12A 0.9600 . ?
C12 H12B 0.9600 . ?
C12 H12C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 P1 P1 99.59(4) . 3_666 ?
C2 C1 C6 120.58(9) . . ?
C2 C1 P1 119.74(8) . . ?
C6 C1 P1 119.63(8) . . ?
C3 C2 C1 118.71(10) . . ?
C3 C2 C7 119.66(10) . . ?
C1 C2 C7 121.62(9) . . ?
C4 C3 C2 120.77(11) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C5 C4 C3 120.23(10) . . ?
C5 C4 H4 119.9 . . ?
C3 C4 H4 119.9 . . ?
C4 C5 C6 121.00(10) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C5 C6 C1 118.59(10) . . ?
C5 C6 C10 119.38(10) . . ?
C1 C6 C10 122.02(9) . . ?
C2 C7 C8 110.69(9) . . ?
C2 C7 C9 112.50(9) . . ?
C8 C7 C9 111.14(10) . . ?
C2 C7 H7 107.4 . . ?
C8 C7 H7 107.4 . . ?
C9 C7 H7 107.4 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C6 C10 C12 112.14(9) . . ?
C6 C10 C11 110.49(10) . . ?
C12 C10 C11 111.69(10) . . ?
C6 C10 H10 107.4 . . ?
C12 C10 H10 107.4 . . ?
C11 C10 H10 107.4 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
P1 P1 C1 C2 91.75(8) 3_666 . . . ?
P1 P1 C1 C6 -90.80(8) 3_666 . . . ?
C6 C1 C2 C3 3.58(15) . . . . ?
P1 C1 C2 C3 -179.00(8) . . . . ?
C6 C1 C2 C7 -177.18(10) . . . . ?
P1 C1 C2 C7 0.25(14) . . . . ?
C1 C2 C3 C4 -0.97(17) . . . . ?
C7 C2 C3 C4 179.77(10) . . . . ?
C2 C3 C4 C5 -1.51(18) . . . . ?
C3 C4 C5 C6 1.40(18) . . . . ?
C4 C5 C6 C1 1.18(17) . . . . ?
C4 C5 C6 C10 -179.62(10) . . . . ?
C2 C1 C6 C5 -3.68(15) . . . . ?
P1 C1 C6 C5 178.89(8) . . . . ?
C2 C1 C6 C10 177.14(10) . . . . ?
P1 C1 C6 C10 -0.29(14) . . . . ?
C3 C2 C7 C8 77.77(13) . . . . ?
C1 C2 C7 C8 -101.47(12) . . . . ?
C3 C2 C7 C9 -47.25(14) . . . . ?
C1 C2 C7 C9 133.52(11) . . . . ?
C5 C6 C10 C12 49.89(14) . . . . ?
C1 C6 C10 C12 -130.93(11) . . . . ?
C5 C6 C10 C11 -75.41(13) . . . . ?
C1 C6 C10 C11 103.77(12) . . . . ?

_refine_diff_density_max         0.359
_refine_diff_density_min         -0.156
_refine_diff_density_rms         0.046

####################################################################### 
# 
# 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_ax1669_Tip2P2Br2_cmpd_RR_1
_database_code_depnum_ccdc_archive 'CCDC 2098826'
loop_
_audit_author_name
_audit_author_address
'Christian Hering-Junghans'
;Leibniz Institute for Catalysis Rostock
Germany
;
_audit_update_record             
;
2021-07-23 deposited with the CCDC.	2021-09-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7

#==============================================================================

# CHEMICAL DATA

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H46 Br2 P2'
_chemical_formula_sum            'C30 H46 Br2 P2'
_chemical_formula_weight         628.43

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'
Br Br -0.2901 2.4595 '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                   9.7477(16)
_cell_length_b                   12.232(2)
_cell_length_c                   13.591(2)
_cell_angle_alpha                90.634(4)
_cell_angle_beta                 102.776(3)
_cell_angle_gamma                96.594(3)
_cell_volume                     1568.8(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9773
_cell_measurement_theta_min      2.32
_cell_measurement_theta_max      30.59

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.330
_exptl_crystal_F_000             652
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.322
_exptl_crystal_size_mid          0.242
_exptl_crystal_size_min          0.162
_exptl_absorpt_coefficient_mu    2.702
_shelx_estimated_absorpt_T_min   0.477
_shelx_estimated_absorpt_T_max   0.669
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.59
_exptl_absorpt_correction_T_max  0.67
_exptl_absorpt_process_details   'SADABS (Bruker, 2014)'
_exptl_absorpt_special_details   ?

#==============================================================================

# EXPERIMENTAL DATA

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            76651
_diffrn_reflns_av_unetI/netI     0.0168
_diffrn_reflns_av_R_equivalents  0.0276
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.537
_diffrn_reflns_theta_max         30.630
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             9672
_reflns_number_gt                8242
_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       'APEX2 (Bruker, 2014)'
_computing_cell_refinement       'SAINT (Bruker, 2013)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP-3v2.01 (Farrugia, 1997)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'

#==============================================================================

# REFINEMENT DATA 

_refine_special_details          
;
 All H atoms 
 were positioned geometrically and refined using a riding model, with C---H = 
 0.98 (methyl groups), 0.99Å (methylene groups), 1.00Å (methine groups) or 
 0.95 Å (aryl CH) and with Uiso(H) = 1.5 times Ueq(C) 
 (methyl groups) or with Uiso(H) = 1.2 times Ueq(C) 
 (methylene  groups, aryl CH, methine groups). Torsion angles of the methyl 
 groups on one Tipp-group were allowed to refine. The second Tipp-group was
 found to be disordered and was split in two parts. The occupancy of each
 was allowed to refine freely.
 
 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 > 2σ(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     
'w=1/[σ²(Fo²)+(0.0383P)²+0.5487P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         9672
_refine_ls_number_parameters     443
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0342
_refine_ls_R_factor_gt           0.0261
_refine_ls_wR_factor_ref         0.0713
_refine_ls_wR_factor_gt          0.0674
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_restrained_S_all      1.026
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

#==============================================================================

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

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
P1 P -0.13245(4) 0.24809(3) 0.12034(3) 0.02173(7) Uani 1 1 d . . . . .
P2 P -0.01442(4) 0.29674(3) 0.27831(2) 0.02021(7) Uani 1 1 d . . . . .
Br1 Br 0.01057(2) 0.14189(2) 0.06454(2) 0.03399(5) Uani 1 1 d . . . . .
Br2 Br 0.19774(2) 0.37323(2) 0.25749(2) 0.03112(4) Uani 1 1 d . . . . .
C1A C -0.2591(11) 0.1503(12) 0.1644(10) 0.0219(15) Uani 0.628(10) 1 d . . P A 1
C2A C -0.4059(7) 0.1690(5) 0.1317(5) 0.0270(10) Uani 0.628(10) 1 d . . P A 1
C3A C -0.5125(5) 0.1060(5) 0.1672(4) 0.0330(10) Uani 0.628(10) 1 d . . P A 1
H3A H -0.6073 0.1222 0.1456 0.040 Uiso 0.628(10) 1 calc R U P A 1
C4A C -0.4863(5) 0.0228(4) 0.2311(4) 0.0339(9) Uani 0.628(10) 1 d . . P A 1
C5A C -0.3475(6) 0.0002(4) 0.2616(4) 0.0328(9) Uani 0.628(10) 1 d . . P A 1
H5A H -0.3282 -0.0590 0.3053 0.039 Uiso 0.628(10) 1 calc R U P A 1
C6A C -0.2344(7) 0.0608(7) 0.2310(6) 0.0223(10) Uani 0.628(10) 1 d . . P A 1
C7A C -0.4518(6) 0.2582(5) 0.0567(5) 0.0355(11) Uani 0.628(10) 1 d . . P A 1
H7A H -0.3680 0.2857 0.0288 0.043 Uiso 0.628(10) 1 calc R U P A 1
C8A C -0.5721(5) 0.2170(6) -0.0323(4) 0.0580(15) Uani 0.628(10) 1 d . . P A 1
H8A1 H -0.5458 0.1545 -0.0667 0.087 Uiso 0.628(10) 1 calc R U P A 1
H8A2 H -0.6579 0.1937 -0.0079 0.087 Uiso 0.628(10) 1 calc R U P A 1
H8A3 H -0.5901 0.2764 -0.0796 0.087 Uiso 0.628(10) 1 calc R U P A 1
C9A C -0.4911(11) 0.3559(6) 0.1113(9) 0.0402(14) Uani 0.628(10) 1 d . . P A 1
H9A1 H -0.4130 0.3818 0.1684 0.060 Uiso 0.628(10) 1 calc R U P A 1
H9A2 H -0.5089 0.4157 0.0644 0.060 Uiso 0.628(10) 1 calc R U P A 1
H9A3 H -0.5767 0.3330 0.1361 0.060 Uiso 0.628(10) 1 calc R U P A 1
C10A C -0.6031(6) -0.0436(4) 0.2708(5) 0.0569(13) Uani 0.628(10) 1 d . . P A 1
H10A H -0.5547 -0.0953 0.3195 0.068 Uiso 0.628(10) 1 calc R U P A 1
C11A C -0.6717(7) 0.0308(6) 0.3329(6) 0.0729(18) Uani 0.628(10) 1 d . . P A 1
H11A H -0.7465 -0.0134 0.3577 0.109 Uiso 0.628(10) 1 calc R U P A 1
H11B H -0.5997 0.0651 0.3903 0.109 Uiso 0.628(10) 1 calc R U P A 1
H11C H -0.7127 0.0883 0.2902 0.109 Uiso 0.628(10) 1 calc R U P A 1
C12A C -0.7044(12) -0.1185(12) 0.1836(10) 0.101(3) Uani 0.628(10) 1 d . . P A 1
H12A H -0.7790 -0.1607 0.2101 0.151 Uiso 0.628(10) 1 calc R U P A 1
H12B H -0.7474 -0.0721 0.1297 0.151 Uiso 0.628(10) 1 calc R U P A 1
H12C H -0.6500 -0.1692 0.1564 0.151 Uiso 0.628(10) 1 calc R U P A 1
C13A C -0.0908(7) 0.0243(6) 0.2687(5) 0.0272(11) Uani 0.628(10) 1 d . . P A 1
H13A H -0.0192 0.0797 0.2487 0.033 Uiso 0.628(10) 1 calc R U P A 1
C14A C -0.0861(8) -0.0908(6) 0.2138(6) 0.0418(12) Uani 0.628(10) 1 d . . P A 1
H14A H 0.0073 -0.1155 0.2378 0.063 Uiso 0.628(10) 1 calc R U P A 1
H14B H -0.1592 -0.1456 0.2291 0.063 Uiso 0.628(10) 1 calc R U P A 1
H14C H -0.1034 -0.0819 0.1406 0.063 Uiso 0.628(10) 1 calc R U P A 1
C15A C -0.0489(6) 0.0142(5) 0.3816(5) 0.0380(10) Uani 0.628(10) 1 d . . P A 1
H15A H 0.0457 -0.0099 0.4000 0.057 Uiso 0.628(10) 1 calc R U P A 1
H15B H -0.0477 0.0858 0.4150 0.057 Uiso 0.628(10) 1 calc R U P A 1
H15C H -0.1174 -0.0399 0.4032 0.057 Uiso 0.628(10) 1 calc R U P A 1
C1B C -0.2864(16) 0.1590(18) 0.1545(14) 0.017(2) Uani 0.372(10) 1 d . . P A 2
C2B C -0.2657(13) 0.0684(13) 0.2119(9) 0.0221(16) Uani 0.372(10) 1 d . . P A 2
C3B C -0.3868(9) 0.0133(6) 0.2369(6) 0.0258(14) Uani 0.372(10) 1 d . . P A 2
H3B H -0.3782 -0.0499 0.2768 0.031 Uiso 0.372(10) 1 calc R U P A 2
C4B C -0.5190(8) 0.0490(6) 0.2050(6) 0.0266(13) Uani 0.372(10) 1 d . . P A 2
C5B C -0.5306(7) 0.1380(7) 0.1469(6) 0.0257(13) Uani 0.372(10) 1 d . . P A 2
H5B H -0.6217 0.1614 0.1246 0.031 Uiso 0.372(10) 1 calc R U P A 2
C6B C -0.4153(10) 0.1978(7) 0.1178(8) 0.0201(14) Uani 0.372(10) 1 d . . P A 2
C7B C -0.1252(11) 0.0186(11) 0.2495(8) 0.0239(17) Uani 0.372(10) 1 d . . P A 2
H7B H -0.0464 0.0715 0.2352 0.029 Uiso 0.372(10) 1 calc R U P A 2
C8B C -0.0959(8) 0.0033(9) 0.3656(8) 0.0368(17) Uani 0.372(10) 1 d . . P A 2
H8B1 H -0.0956 0.0741 0.4003 0.055 Uiso 0.372(10) 1 calc R U P A 2
H8B2 H -0.1701 -0.0503 0.3813 0.055 Uiso 0.372(10) 1 calc R U P A 2
H8B3 H -0.0035 -0.0235 0.3884 0.055 Uiso 0.372(10) 1 calc R U P A 2
C9B C -0.1263(13) -0.0844(12) 0.1962(12) 0.049(3) Uani 0.372(10) 1 d . . P A 2
H9B1 H -0.0364 -0.1142 0.2213 0.073 Uiso 0.372(10) 1 calc R U P A 2
H9B2 H -0.2047 -0.1370 0.2073 0.073 Uiso 0.372(10) 1 calc R U P A 2
H9B3 H -0.1385 -0.0721 0.1238 0.073 Uiso 0.372(10) 1 calc R U P A 2
C10B C -0.6477(6) -0.0113(6) 0.2363(5) 0.0389(15) Uani 0.372(10) 1 d . . P A 2
H10B H -0.7340 0.0248 0.2073 0.047 Uiso 0.372(10) 1 calc R U P A 2
C11B C -0.6239(11) -0.0117(12) 0.3522(9) 0.079(3) Uani 0.372(10) 1 d . . P A 2
H11D H -0.6047 0.0643 0.3798 0.119 Uiso 0.372(10) 1 calc R U P A 2
H11E H -0.7089 -0.0482 0.3708 0.119 Uiso 0.372(10) 1 calc R U P A 2
H11F H -0.5430 -0.0515 0.3798 0.119 Uiso 0.372(10) 1 calc R U P A 2
C12B C -0.671(2) -0.117(2) 0.2127(18) 0.101(3) Uani 0.372(10) 1 d . . P A 2
H12D H -0.7555 -0.1495 0.2353 0.151 Uiso 0.372(10) 1 calc R U P A 2
H12E H -0.6874 -0.1284 0.1393 0.151 Uiso 0.372(10) 1 calc R U P A 2
H12F H -0.5893 -0.1531 0.2457 0.151 Uiso 0.372(10) 1 calc R U P A 2
C13B C -0.4388(11) 0.2984(7) 0.0601(9) 0.0348(19) Uani 0.372(10) 1 d . . P A 2
H13B H -0.3454 0.3315 0.0483 0.042 Uiso 0.372(10) 1 calc R U P A 2
C14B C -0.5380(15) 0.2660(11) -0.0442(7) 0.075(4) Uani 0.372(10) 1 d . . P A 2
H14D H -0.5540 0.3323 -0.0828 0.113 Uiso 0.372(10) 1 calc R U P A 2
H14E H -0.4940 0.2158 -0.0810 0.113 Uiso 0.372(10) 1 calc R U P A 2
H14F H -0.6287 0.2293 -0.0347 0.113 Uiso 0.372(10) 1 calc R U P A 2
C15B C -0.498(2) 0.3858(10) 0.1148(17) 0.043(2) Uani 0.372(10) 1 d . . P A 2
H15D H -0.5108 0.4499 0.0726 0.065 Uiso 0.372(10) 1 calc R U P A 2
H15E H -0.5891 0.3552 0.1280 0.065 Uiso 0.372(10) 1 calc R U P A 2
H15F H -0.4312 0.4083 0.1790 0.065 Uiso 0.372(10) 1 calc R U P A 2
C16 C -0.11509(13) 0.41272(10) 0.29128(10) 0.0197(2) Uani 1 1 d . . . . .
C17 C -0.12601(13) 0.50633(11) 0.23054(10) 0.0205(2) Uani 1 1 d . . . . .
C18 C -0.20582(14) 0.58695(11) 0.25262(10) 0.0229(2) Uani 1 1 d . . . . .
H18 H -0.2119 0.6501 0.2125 0.027 Uiso 1 1 calc R U . . .
C19 C -0.27687(14) 0.57907(11) 0.33066(10) 0.0238(3) Uani 1 1 d . . . . .
C20 C -0.26636(15) 0.48683(12) 0.38854(11) 0.0256(3) Uani 1 1 d . . . . .
H20 H -0.3147 0.4801 0.4421 0.031 Uiso 1 1 calc R U . . .
C21 C -0.18763(15) 0.40360(11) 0.37132(10) 0.0231(2) Uani 1 1 d . . . . .
C22 C -0.05596(15) 0.52703(11) 0.14155(10) 0.0241(3) Uani 1 1 d . . . . .
H22 H -0.0112 0.4600 0.1295 0.029 Uiso 1 1 calc R U . . .
C23 C -0.16455(19) 0.54637(15) 0.04496(12) 0.0350(3) Uani 1 1 d . . . . .
H23A H -0.2381 0.4830 0.0300 0.053 Uiso 1 1 calc R U . . .
H23B H -0.1170 0.5555 -0.0114 0.053 Uiso 1 1 calc R U . . .
H23C H -0.2080 0.6130 0.0545 0.053 Uiso 1 1 calc R U . . .
C24 C 0.06074(18) 0.62487(12) 0.16518(13) 0.0341(3) Uani 1 1 d . . . . .
H24A H 0.0190 0.6918 0.1767 0.051 Uiso 1 1 calc R U . . .
H24B H 0.1067 0.6347 0.1081 0.051 Uiso 1 1 calc R U . . .
H24C H 0.1311 0.6108 0.2259 0.051 Uiso 1 1 calc R U . . .
C25 C -0.36492(16) 0.66827(12) 0.34984(12) 0.0288(3) Uani 1 1 d . . . . .
H25 H -0.3579 0.7256 0.2987 0.035 Uiso 1 1 calc R U . . .
C26 C -0.3087(2) 0.72381(16) 0.45354(14) 0.0472(4) Uani 1 1 d . . . . .
H26A H -0.3178 0.6702 0.5055 0.071 Uiso 1 1 calc R U . . .
H26B H -0.3632 0.7846 0.4612 0.071 Uiso 1 1 calc R U . . .
H26C H -0.2087 0.7525 0.4610 0.071 Uiso 1 1 calc R U . . .
C27 C -0.5210(2) 0.62224(18) 0.33453(19) 0.0521(5) Uani 1 1 d . . . . .
H27A H -0.5556 0.5906 0.2657 0.078 Uiso 1 1 calc R U . . .
H27B H -0.5763 0.6817 0.3449 0.078 Uiso 1 1 calc R U . . .
H27C H -0.5312 0.5650 0.3831 0.078 Uiso 1 1 calc R U . . .
C28 C -0.18617(18) 0.30605(12) 0.44002(12) 0.0309(3) Uani 1 1 d . . . . .
H28 H -0.1264 0.2534 0.4183 0.037 Uiso 1 1 calc R U . . .
C29 C -0.1201(2) 0.34145(17) 0.55050(14) 0.0466(4) Uani 1 1 d . . . . .
H29A H -0.1794 0.3904 0.5748 0.070 Uiso 1 1 calc R U . . .
H29B H -0.0250 0.3804 0.5556 0.070 Uiso 1 1 calc R U . . .
H29C H -0.1137 0.2762 0.5917 0.070 Uiso 1 1 calc R U . . .
C30 C -0.3346(2) 0.24593(16) 0.42945(15) 0.0486(5) Uani 1 1 d . . . . .
H30A H -0.3935 0.2937 0.4556 0.073 Uiso 1 1 calc R U . . .
H30B H -0.3294 0.1786 0.4679 0.073 Uiso 1 1 calc R U . . .
H30C H -0.3764 0.2267 0.3581 0.073 Uiso 1 1 calc R U . . .


#==============================================================================

# MOLECULAR GEOMETRY

_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 C1A 1.821(14) . ?
P1 C1B 1.90(2) . ?
P1 P2 2.2382(6) . ?
P1 Br1 2.2512(4) . ?
P2 C16 1.8431(13) . ?
P2 Br2 2.2478(5) . ?
C1A C6A 1.436(13) . ?
C1A C2A 1.447(9) . ?
C2A C3A 1.397(8) . ?
C2A C7A 1.538(7) . ?
C3A C4A 1.355(5) . ?
C3A H3A 0.9500 . ?
C4A C5A 1.385(5) . ?
C4A C10A 1.522(6) . ?
C5A C6A 1.400(11) . ?
C5A H5A 0.9500 . ?
C6A C13A 1.501(9) . ?
C7A C8A 1.522(8) . ?
C7A C9A 1.529(9) . ?
C7A H7A 1.0000 . ?
C8A H8A1 0.9800 . ?
C8A H8A2 0.9800 . ?
C8A H8A3 0.9800 . ?
C9A H9A1 0.9800 . ?
C9A H9A2 0.9800 . ?
C9A H9A3 0.9800 . ?
C10A C11A 1.537(8) . ?
C10A C12A 1.571(10) . ?
C10A H10A 1.0000 . ?
C11A H11A 0.9800 . ?
C11A H11B 0.9800 . ?
C11A H11C 0.9800 . ?
C12A H12A 0.9800 . ?
C12A H12B 0.9800 . ?
C12A H12C 0.9800 . ?
C13A C15A 1.509(8) . ?
C13A C14A 1.596(11) . ?
C13A H13A 1.0000 . ?
C14A H14A 0.9800 . ?
C14A H14B 0.9800 . ?
C14A H14C 0.9800 . ?
C15A H15A 0.9800 . ?
C15A H15B 0.9800 . ?
C15A H15C 0.9800 . ?
C1B C2B 1.37(2) . ?
C1B C6B 1.384(15) . ?
C2B C3B 1.401(18) . ?
C2B C7B 1.548(16) . ?
C3B C4B 1.387(8) . ?
C3B H3B 0.9500 . ?
C4B C5B 1.354(7) . ?
C4B C10B 1.526(9) . ?
C5B C6B 1.403(13) . ?
C5B H5B 0.9500 . ?
C6B C13B 1.480(10) . ?
C7B C9B 1.44(2) . ?
C7B C8B 1.558(14) . ?
C7B H7B 1.0000 . ?
C8B H8B1 0.9800 . ?
C8B H8B2 0.9800 . ?
C8B H8B3 0.9800 . ?
C9B H9B1 0.9800 . ?
C9B H9B2 0.9800 . ?
C9B H9B3 0.9800 . ?
C10B C12B 1.31(3) . ?
C10B C11B 1.541(14) . ?
C10B H10B 1.0000 . ?
C11B H11D 0.9800 . ?
C11B H11E 0.9800 . ?
C11B H11F 0.9800 . ?
C12B H12D 0.9800 . ?
C12B H12E 0.9800 . ?
C12B H12F 0.9800 . ?
C13B C15B 1.529(18) . ?
C13B C14B 1.547(16) . ?
C13B H13B 1.0000 . ?
C14B H14D 0.9800 . ?
C14B H14E 0.9800 . ?
C14B H14F 0.9800 . ?
C15B H15D 0.9800 . ?
C15B H15E 0.9800 . ?
C15B H15F 0.9800 . ?
C16 C17 1.4192(18) . ?
C16 C21 1.4215(18) . ?
C17 C18 1.3931(18) . ?
C17 C22 1.5249(18) . ?
C18 C19 1.3877(18) . ?
C18 H18 0.9500 . ?
C19 C20 1.383(2) . ?
C19 C25 1.5175(19) . ?
C20 C21 1.3905(19) . ?
C20 H20 0.9500 . ?
C21 C28 1.523(2) . ?
C22 C24 1.532(2) . ?
C22 C23 1.533(2) . ?
C22 H22 1.0000 . ?
C23 H23A 0.9800 . ?
C23 H23B 0.9800 . ?
C23 H23C 0.9800 . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 C26 1.517(2) . ?
C25 C27 1.528(2) . ?
C25 H25 1.0000 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 0.9800 . ?
C28 C30 1.522(2) . ?
C28 C29 1.533(2) . ?
C28 H28 1.0000 . ?
C29 H29A 0.9800 . ?
C29 H29B 0.9800 . ?
C29 H29C 0.9800 . ?
C30 H30A 0.9800 . ?
C30 H30B 0.9800 . ?
C30 H30C 0.9800 . ?

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
C1A P1 P2 92.1(4) . . ?
C1B P1 P2 97.0(6) . . ?
C1A P1 Br1 104.2(4) . . ?
C1B P1 Br1 110.2(6) . . ?
P2 P1 Br1 103.243(19) . . ?
C16 P2 P1 95.00(4) . . ?
C16 P2 Br2 105.73(4) . . ?
P1 P2 Br2 103.017(18) . . ?
C6A C1A C2A 115.1(10) . . ?
C6A C1A P1 129.6(7) . . ?
C2A C1A P1 115.2(8) . . ?
C3A C2A C1A 121.0(7) . . ?
C3A C2A C7A 117.1(5) . . ?
C1A C2A C7A 121.9(8) . . ?
C4A C3A C2A 122.7(4) . . ?
C4A C3A H3A 118.7 . . ?
C2A C3A H3A 118.7 . . ?
C3A C4A C5A 117.9(4) . . ?
C3A C4A C10A 122.1(4) . . ?
C5A C4A C10A 120.0(5) . . ?
C4A C5A C6A 122.9(4) . . ?
C4A C5A H5A 118.6 . . ?
C6A C5A H5A 118.6 . . ?
C5A C6A C1A 120.3(6) . . ?
C5A C6A C13A 116.4(6) . . ?
C1A C6A C13A 123.2(8) . . ?
C8A C7A C9A 110.1(6) . . ?
C8A C7A C2A 114.0(4) . . ?
C9A C7A C2A 110.5(6) . . ?
C8A C7A H7A 107.3 . . ?
C9A C7A H7A 107.3 . . ?
C2A C7A H7A 107.3 . . ?
C7A C8A H8A1 109.5 . . ?
C7A C8A H8A2 109.5 . . ?
H8A1 C8A H8A2 109.5 . . ?
C7A C8A H8A3 109.5 . . ?
H8A1 C8A H8A3 109.5 . . ?
H8A2 C8A H8A3 109.5 . . ?
C7A C9A H9A1 109.5 . . ?
C7A C9A H9A2 109.5 . . ?
H9A1 C9A H9A2 109.5 . . ?
C7A C9A H9A3 109.5 . . ?
H9A1 C9A H9A3 109.5 . . ?
H9A2 C9A H9A3 109.5 . . ?
C4A C10A C11A 110.7(4) . . ?
C4A C10A C12A 110.3(6) . . ?
C11A C10A C12A 117.4(8) . . ?
C4A C10A H10A 105.8 . . ?
C11A C10A H10A 105.8 . . ?
C12A C10A H10A 105.8 . . ?
C10A C11A H11A 109.5 . . ?
C10A C11A H11B 109.5 . . ?
H11A C11A H11B 109.5 . . ?
C10A C11A H11C 109.5 . . ?
H11A C11A H11C 109.5 . . ?
H11B C11A H11C 109.5 . . ?
C10A C12A H12A 109.5 . . ?
C10A C12A H12B 109.5 . . ?
H12A C12A H12B 109.5 . . ?
C10A C12A H12C 109.5 . . ?
H12A C12A H12C 109.5 . . ?
H12B C12A H12C 109.5 . . ?
C6A C13A C15A 114.5(7) . . ?
C6A C13A C14A 108.7(5) . . ?
C15A C13A C14A 109.7(6) . . ?
C6A C13A H13A 107.9 . . ?
C15A C13A H13A 107.9 . . ?
C14A C13A H13A 107.9 . . ?
C13A C14A H14A 109.5 . . ?
C13A C14A H14B 109.5 . . ?
H14A C14A H14B 109.5 . . ?
C13A C14A H14C 109.5 . . ?
H14A C14A H14C 109.5 . . ?
H14B C14A H14C 109.5 . . ?
C13A C15A H15A 109.5 . . ?
C13A C15A H15B 109.5 . . ?
H15A C15A H15B 109.5 . . ?
C13A C15A H15C 109.5 . . ?
H15A C15A H15C 109.5 . . ?
H15B C15A H15C 109.5 . . ?
C2B C1B C6B 125.8(15) . . ?
C2B C1B P1 121.4(11) . . ?
C6B C1B P1 112.8(13) . . ?
C1B C2B C3B 115.8(11) . . ?
C1B C2B C7B 127.5(13) . . ?
C3B C2B C7B 116.7(10) . . ?
C4B C3B C2B 121.6(7) . . ?
C4B C3B H3B 119.2 . . ?
C2B C3B H3B 119.2 . . ?
C5B C4B C3B 118.8(7) . . ?
C5B C4B C10B 121.2(7) . . ?
C3B C4B C10B 120.0(6) . . ?
C4B C5B C6B 123.5(6) . . ?
C4B C5B H5B 118.3 . . ?
C6B C5B H5B 118.3 . . ?
C1B C6B C5B 114.4(10) . . ?
C1B C6B C13B 126.6(12) . . ?
C5B C6B C13B 118.7(7) . . ?
C9B C7B C2B 111.0(8) . . ?
C9B C7B C8B 110.8(10) . . ?
C2B C7B C8B 110.9(11) . . ?
C9B C7B H7B 108.0 . . ?
C2B C7B H7B 108.0 . . ?
C8B C7B H7B 108.0 . . ?
C7B C8B H8B1 109.5 . . ?
C7B C8B H8B2 109.5 . . ?
H8B1 C8B H8B2 109.5 . . ?
C7B C8B H8B3 109.5 . . ?
H8B1 C8B H8B3 109.5 . . ?
H8B2 C8B H8B3 109.5 . . ?
C7B C9B H9B1 109.5 . . ?
C7B C9B H9B2 109.5 . . ?
H9B1 C9B H9B2 109.5 . . ?
C7B C9B H9B3 109.5 . . ?
H9B1 C9B H9B3 109.5 . . ?
H9B2 C9B H9B3 109.5 . . ?
C12B C10B C4B 114.8(13) . . ?
C12B C10B C11B 101.4(15) . . ?
C4B C10B C11B 110.7(6) . . ?
C12B C10B H10B 109.9 . . ?
C4B C10B H10B 109.9 . . ?
C11B C10B H10B 109.9 . . ?
C10B C11B H11D 109.5 . . ?
C10B C11B H11E 109.5 . . ?
H11D C11B H11E 109.5 . . ?
C10B C11B H11F 109.5 . . ?
H11D C11B H11F 109.5 . . ?
H11E C11B H11F 109.5 . . ?
C10B C12B H12D 109.5 . . ?
C10B C12B H12E 109.5 . . ?
H12D C12B H12E 109.5 . . ?
C10B C12B H12F 109.5 . . ?
H12D C12B H12F 109.5 . . ?
H12E C12B H12F 109.5 . . ?
C6B C13B C15B 113.7(11) . . ?
C6B C13B C14B 109.0(7) . . ?
C15B C13B C14B 110.6(11) . . ?
C6B C13B H13B 107.8 . . ?
C15B C13B H13B 107.8 . . ?
C14B C13B H13B 107.8 . . ?
C13B C14B H14D 109.5 . . ?
C13B C14B H14E 109.5 . . ?
H14D C14B H14E 109.5 . . ?
C13B C14B H14F 109.5 . . ?
H14D C14B H14F 109.5 . . ?
H14E C14B H14F 109.5 . . ?
C13B C15B H15D 109.5 . . ?
C13B C15B H15E 109.5 . . ?
H15D C15B H15E 109.5 . . ?
C13B C15B H15F 109.5 . . ?
H15D C15B H15F 109.5 . . ?
H15E C15B H15F 109.5 . . ?
C17 C16 C21 118.97(12) . . ?
C17 C16 P2 126.76(10) . . ?
C21 C16 P2 114.27(10) . . ?
C18 C17 C16 118.68(12) . . ?
C18 C17 C22 116.27(12) . . ?
C16 C17 C22 125.04(11) . . ?
C19 C18 C17 122.87(13) . . ?
C19 C18 H18 118.6 . . ?
C17 C18 H18 118.6 . . ?
C20 C19 C18 117.76(12) . . ?
C20 C19 C25 121.64(12) . . ?
C18 C19 C25 120.59(13) . . ?
C19 C20 C21 122.47(12) . . ?
C19 C20 H20 118.8 . . ?
C21 C20 H20 118.8 . . ?
C20 C21 C16 119.25(12) . . ?
C20 C21 C28 117.07(12) . . ?
C16 C21 C28 123.67(12) . . ?
C17 C22 C24 110.95(12) . . ?
C17 C22 C23 111.56(12) . . ?
C24 C22 C23 110.07(13) . . ?
C17 C22 H22 108.0 . . ?
C24 C22 H22 108.0 . . ?
C23 C22 H22 108.0 . . ?
C22 C23 H23A 109.5 . . ?
C22 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C22 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C22 C24 H24A 109.5 . . ?
C22 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C22 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C26 C25 C19 111.76(13) . . ?
C26 C25 C27 111.41(15) . . ?
C19 C25 C27 110.83(13) . . ?
C26 C25 H25 107.5 . . ?
C19 C25 H25 107.5 . . ?
C27 C25 H25 107.5 . . ?
C25 C26 H26A 109.5 . . ?
C25 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C25 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C25 C27 H27A 109.5 . . ?
C25 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C25 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 109.5 . . ?
C30 C28 C21 111.01(14) . . ?
C30 C28 C29 110.73(14) . . ?
C21 C28 C29 111.61(13) . . ?
C30 C28 H28 107.8 . . ?
C21 C28 H28 107.8 . . ?
C29 C28 H28 107.8 . . ?
C28 C29 H29A 109.5 . . ?
C28 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C28 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C28 C30 H30A 109.5 . . ?
C28 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C28 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
P2 P1 C1A C6A -54.2(12) . . . . ?
Br1 P1 C1A C6A 50.0(12) . . . . ?
P2 P1 C1A C2A 122.1(8) . . . . ?
Br1 P1 C1A C2A -133.6(8) . . . . ?
C6A C1A C2A C3A 2.5(14) . . . . ?
P1 C1A C2A C3A -174.4(6) . . . . ?
C6A C1A C2A C7A -177.4(8) . . . . ?
P1 C1A C2A C7A 5.7(12) . . . . ?
C1A C2A C3A C4A -1.9(10) . . . . ?
C7A C2A C3A C4A 178.0(5) . . . . ?
C2A C3A C4A C5A -0.1(7) . . . . ?
C2A C3A C4A C10A 178.8(5) . . . . ?
C3A C4A C5A C6A 1.3(8) . . . . ?
C10A C4A C5A C6A -177.5(5) . . . . ?
C4A C5A C6A C1A -0.6(12) . . . . ?
C4A C5A C6A C13A -178.6(6) . . . . ?
C2A C1A C6A C5A -1.3(15) . . . . ?
P1 C1A C6A C5A 175.0(8) . . . . ?
C2A C1A C6A C13A 176.5(8) . . . . ?
P1 C1A C6A C13A -7.1(17) . . . . ?
C3A C2A C7A C8A -50.8(7) . . . . ?
C1A C2A C7A C8A 129.1(8) . . . . ?
C3A C2A C7A C9A 73.9(8) . . . . ?
C1A C2A C7A C9A -106.2(9) . . . . ?
C3A C4A C10A C11A -61.7(7) . . . . ?
C5A C4A C10A C11A 117.1(6) . . . . ?
C3A C4A C10A C12A 69.9(9) . . . . ?
C5A C4A C10A C12A -111.3(9) . . . . ?
C5A C6A C13A C15A -52.9(9) . . . . ?
C1A C6A C13A C15A 129.2(10) . . . . ?
C5A C6A C13A C14A 70.2(9) . . . . ?
C1A C6A C13A C14A -107.7(10) . . . . ?
P2 P1 C1B C2B -60.0(17) . . . . ?
Br1 P1 C1B C2B 46.9(18) . . . . ?
P2 P1 C1B C6B 118.5(13) . . . . ?
Br1 P1 C1B C6B -134.6(12) . . . . ?
C6B C1B C2B C3B -2(3) . . . . ?
P1 C1B C2B C3B 176.3(11) . . . . ?
C6B C1B C2B C7B 176.4(15) . . . . ?
P1 C1B C2B C7B -5(3) . . . . ?
C1B C2B C3B C4B 0.2(19) . . . . ?
C7B C2B C3B C4B -178.3(9) . . . . ?
C2B C3B C4B C5B 1.1(13) . . . . ?
C2B C3B C4B C10B -178.3(9) . . . . ?
C3B C4B C5B C6B -0.8(12) . . . . ?
C10B C4B C5B C6B 178.6(8) . . . . ?
C2B C1B C6B C5B 2(3) . . . . ?
P1 C1B C6B C5B -176.2(9) . . . . ?
C2B C1B C6B C13B 176.8(16) . . . . ?
P1 C1B C6B C13B -2(2) . . . . ?
C4B C5B C6B C1B -0.7(16) . . . . ?
C4B C5B C6B C13B -175.8(9) . . . . ?
C1B C2B C7B C9B -108.4(18) . . . . ?
C3B C2B C7B C9B 69.9(15) . . . . ?
C1B C2B C7B C8B 127.9(17) . . . . ?
C3B C2B C7B C8B -53.8(14) . . . . ?
C5B C4B C10B C12B 124.9(14) . . . . ?
C3B C4B C10B C12B -55.7(15) . . . . ?
C5B C4B C10B C11B -121.1(10) . . . . ?
C3B C4B C10B C11B 58.3(11) . . . . ?
C1B C6B C13B C15B -115.9(17) . . . . ?
C5B C6B C13B C15B 58.4(16) . . . . ?
C1B C6B C13B C14B 120.2(15) . . . . ?
C5B C6B C13B C14B -65.5(13) . . . . ?
P1 P2 C16 C17 -59.56(11) . . . . ?
Br2 P2 C16 C17 45.48(12) . . . . ?
P1 P2 C16 C21 120.33(9) . . . . ?
Br2 P2 C16 C21 -134.63(9) . . . . ?
C21 C16 C17 C18 1.01(19) . . . . ?
P2 C16 C17 C18 -179.11(10) . . . . ?
C21 C16 C17 C22 -179.27(12) . . . . ?
P2 C16 C17 C22 0.61(19) . . . . ?
C16 C17 C18 C19 -0.9(2) . . . . ?
C22 C17 C18 C19 179.34(12) . . . . ?
C17 C18 C19 C20 0.3(2) . . . . ?
C17 C18 C19 C25 -178.65(13) . . . . ?
C18 C19 C20 C21 0.3(2) . . . . ?
C25 C19 C20 C21 179.19(13) . . . . ?
C19 C20 C21 C16 -0.1(2) . . . . ?
C19 C20 C21 C28 -179.43(13) . . . . ?
C17 C16 C21 C20 -0.50(19) . . . . ?
P2 C16 C21 C20 179.60(10) . . . . ?
C17 C16 C21 C28 178.73(13) . . . . ?
P2 C16 C21 C28 -1.17(18) . . . . ?
C18 C17 C22 C24 67.64(16) . . . . ?
C16 C17 C22 C24 -112.08(15) . . . . ?
C18 C17 C22 C23 -55.49(16) . . . . ?
C16 C17 C22 C23 124.79(14) . . . . ?
C20 C19 C25 C26 62.98(19) . . . . ?
C18 C19 C25 C26 -118.13(16) . . . . ?
C20 C19 C25 C27 -61.9(2) . . . . ?
C18 C19 C25 C27 116.94(17) . . . . ?
C20 C21 C28 C30 61.80(18) . . . . ?
C16 C21 C28 C30 -117.45(16) . . . . ?
C20 C21 C28 C29 -62.25(19) . . . . ?
C16 C21 C28 C29 118.50(16) . . . . ?

_refine_diff_density_max         1.215
_refine_diff_density_min         -0.382
_refine_diff_density_rms         0.058

####################################################################### 
# 
# 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_ax2110_Dip4P4_cmpd_4
_database_code_depnum_ccdc_archive 'CCDC 2098828'
loop_
_audit_author_name
_audit_author_address
'Christian Hering-Junghans'
;Leibniz Institute for Catalysis Rostock
Germany
;
_audit_update_record             
;
2021-07-23 deposited with the CCDC.	2021-09-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7

#==============================================================================

# CHEMICAL DATA

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C48 H68 P4, 2 (C6 H6)'
_chemical_formula_sum            'C60 H80 P4'
_chemical_formula_weight         925.12

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'

#==============================================================================

# CRYSTAL DATA

_space_group_crystal_system      tetragonal
_space_group_IT_number           118
_space_group_name_H-M_alt        'P -4 n 2'
_space_group_name_Hall           'P -4 -2n'

_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'
'y, -x, -z'
'-y, x, -z'
'-x, -y, z'
'y+1/2, x+1/2, -z+1/2'
'-y+1/2, -x+1/2, -z+1/2'
'-x+1/2, y+1/2, z+1/2'
'x+1/2, -y+1/2, z+1/2'

_cell_length_a                   11.9767(2)
_cell_length_b                   11.9767(2)
_cell_length_c                   19.3408(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2774.27(11)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    9453
_cell_measurement_theta_min      3.20
_cell_measurement_theta_max      29.79

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.107
_exptl_crystal_F_000             1000
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.240
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.110
_exptl_absorpt_coefficient_mu    0.172
_shelx_estimated_absorpt_T_min   0.960
_shelx_estimated_absorpt_T_max   0.981
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.960
_exptl_absorpt_correction_T_max  0.981
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_absorpt_special_details   ?

#==============================================================================

# EXPERIMENTAL DATA

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            24887
_diffrn_reflns_av_unetI/netI     0.0228
_diffrn_reflns_av_R_equivalents  0.0316
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         2.000
_diffrn_reflns_theta_max         29.993
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4057
_reflns_number_gt                3689
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.836
_reflns_Friedel_fraction_max     1.000
_reflns_Friedel_fraction_full    1.000

_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       'APEX2 (Bruker, 2014)'
_computing_cell_refinement       'SAINT (Bruker, 2013)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP-3v2.01 (Farrugia, 1997)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'

#==============================================================================

# REFINEMENT DATA 

_refine_special_details          
;
 All H atoms 
 were positioned geometrically and refined using a riding model, with C---H = 
 0.98 (methyl groups), 0.99Å (methylene groups), 1.00Å (methine groups) or 
 0.95 Å (aryl CH) and with Uiso(H) = 1.5 times Ueq(C) 
 (methyl groups) or with Uiso(H) = 1.2 times Ueq(C) 
 (methylene  groups, aryl CH, methine groups). Torsion angles of all methyl 
 groups were allowed to refine.
 
 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 > 2σ(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     
'w=1/[σ²(Fo²)+(0.0557P)²+0.3250P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_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 x determined using 1589 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.04(2)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         4057
_refine_ls_number_parameters     151
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0418
_refine_ls_R_factor_gt           0.0357
_refine_ls_wR_factor_ref         0.0951
_refine_ls_wR_factor_gt          0.0897
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

#==============================================================================

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

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
P1 P 0.08639(4) 0.46245(3) 0.19666(2) 0.02452(12) Uani 1 1 d . . . . .
C1 C 0.09585(15) 0.32829(15) 0.14897(9) 0.0251(3) Uani 1 1 d . . . . .
C2 C 0.01077(17) 0.24758(15) 0.13906(10) 0.0280(4) Uani 1 1 d . . . . .
C3 C 0.03427(19) 0.15243(17) 0.09992(12) 0.0368(5) Uani 1 1 d . . . . .
H3 H -0.0237 0.1001 0.0913 0.044 Uiso 1 1 calc R U . . .
C4 C 0.1388(2) 0.13247(19) 0.07357(11) 0.0403(5) Uani 1 1 d . . . . .
H4 H 0.1528 0.0667 0.0475 0.048 Uiso 1 1 calc R U . . .
C5 C 0.2234(2) 0.20843(19) 0.08507(11) 0.0387(5) Uani 1 1 d . . . . .
H5 H 0.2961 0.1934 0.0678 0.046 Uiso 1 1 calc R U . . .
C6 C 0.20395(18) 0.30684(17) 0.12157(10) 0.0335(4) Uani 1 1 d . . . . .
C7 C -0.10612(17) 0.25636(16) 0.16892(11) 0.0302(4) Uani 1 1 d . . . . .
H7 H -0.1073 0.3218 0.2010 0.036 Uiso 1 1 calc R U . . .
C8 C -0.1363(2) 0.15217(19) 0.21115(11) 0.0423(5) Uani 1 1 d . . . . .
H8A H -0.1369 0.0867 0.1808 0.063 Uiso 1 1 calc R U . . .
H8B H -0.2104 0.1619 0.2318 0.063 Uiso 1 1 calc R U . . .
H8C H -0.0809 0.1414 0.2478 0.063 Uiso 1 1 calc R U . . .
C9 C -0.1919(2) 0.2785(2) 0.11179(11) 0.0420(5) Uani 1 1 d . . . . .
H9A H -0.1715 0.3466 0.0867 0.063 Uiso 1 1 calc R U . . .
H9B H -0.2661 0.2877 0.1324 0.063 Uiso 1 1 calc R U . . .
H9C H -0.1931 0.2153 0.0796 0.063 Uiso 1 1 calc R U . . .
C10 C 0.3032(2) 0.3854(2) 0.13006(16) 0.0520(6) Uani 1 1 d . . . A 1
H10 H 0.2744 0.4564 0.1506 0.062 Uiso 1 1 calc R U . A 1
C11 C 0.3867(4) 0.3384(4) 0.1793(3) 0.1121(17) Uani 1 1 d . . . A 1
H11A H 0.3509 0.3248 0.2241 0.168 Uiso 1 1 calc R U . A 1
H11B H 0.4482 0.3915 0.1853 0.168 Uiso 1 1 calc R U . A 1
H11C H 0.4159 0.2679 0.1610 0.168 Uiso 1 1 calc R U . A 1
C12 C 0.3535(4) 0.4138(5) 0.0608(3) 0.127(2) Uani 1 1 d . . . A 1
H12A H 0.3929 0.4853 0.0640 0.191 Uiso 1 1 calc R U . A 1
H12B H 0.2940 0.4194 0.0261 0.191 Uiso 1 1 calc R U . A 1
H12C H 0.4061 0.3552 0.0472 0.191 Uiso 1 1 calc R U . A 1
C20 C 0.0000 0.5000 -0.0039(2) 0.0592(10) Uani 1 2 d S T P B 1
H20 H 0.0000 0.5000 0.0452 0.071 Uiso 1 2 calc R U P B 1
C21 C 0.0467(3) 0.4138(2) -0.03815(15) 0.0589(7) Uani 1 1 d . . . B 1
H21 H 0.0802 0.3543 -0.0131 0.071 Uiso 1 1 calc R U . B 1
C22 C 0.0458(3) 0.4119(3) -0.10800(17) 0.0773(11) Uani 1 1 d . . . B 1
H22 H 0.0765 0.3503 -0.1324 0.093 Uiso 1 1 calc R U . B 1
C23 C 0.0000 0.5000 -0.1433(2) 0.103(2) Uani 1 2 d S T P B 1
H23 H 0.0000 0.5000 -0.1924 0.124 Uiso 1 2 calc R U P B 1


#==============================================================================

# MOLECULAR GEOMETRY

_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 C1 1.8562(18) . ?
P1 P1 2.2231(9) 6 ?
P1 P1 2.2563(9) 4_565 ?
C1 C2 1.417(3) . ?
C1 C6 1.422(3) . ?
C2 C3 1.397(3) . ?
C2 C7 1.518(3) . ?
C3 C4 1.373(3) . ?
C3 H3 0.9500 . ?
C4 C5 1.380(3) . ?
C4 H4 0.9500 . ?
C5 C6 1.394(3) . ?
C5 H5 0.9500 . ?
C6 C10 1.525(3) . ?
C7 C9 1.532(3) . ?
C7 C8 1.534(3) . ?
C7 H7 1.0000 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C11 1.492(5) . ?
C10 C12 1.508(5) . ?
C10 H10 1.0000 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C20 C21 1.348(4) 4_565 ?
C20 C21 1.348(4) . ?
C20 H20 0.9500 . ?
C21 C22 1.351(4) . ?
C21 H21 0.9500 . ?
C22 C23 1.371(4) . ?
C22 H22 0.9500 . ?
C23 C22 1.371(4) 4_565 ?
C23 H23 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 P1 P1 104.45(6) . 6 ?
C1 P1 P1 113.64(6) . 4_565 ?
P1 P1 P1 82.158(14) 6 4_565 ?
C2 C1 C6 118.74(17) . . ?
C2 C1 P1 127.85(15) . . ?
C6 C1 P1 113.39(13) . . ?
C3 C2 C1 119.00(19) . . ?
C3 C2 C7 116.65(17) . . ?
C1 C2 C7 124.35(17) . . ?
C4 C3 C2 121.8(2) . . ?
C4 C3 H3 119.1 . . ?
C2 C3 H3 119.1 . . ?
C3 C4 C5 119.7(2) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
C4 C5 C6 121.1(2) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C5 C6 C1 119.59(19) . . ?
C5 C6 C10 116.5(2) . . ?
C1 C6 C10 123.93(18) . . ?
C2 C7 C9 110.87(17) . . ?
C2 C7 C8 111.30(18) . . ?
C9 C7 C8 111.51(17) . . ?
C2 C7 H7 107.6 . . ?
C9 C7 H7 107.6 . . ?
C8 C7 H7 107.6 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 C12 112.7(4) . . ?
C11 C10 C6 111.0(3) . . ?
C12 C10 C6 110.8(3) . . ?
C11 C10 H10 107.4 . . ?
C12 C10 H10 107.4 . . ?
C6 C10 H10 107.4 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C21 C20 C21 121.2(4) 4_565 . ?
C21 C20 H20 119.4 4_565 . ?
C21 C20 H20 119.4 . . ?
C20 C21 C22 120.0(3) . . ?
C20 C21 H21 120.0 . . ?
C22 C21 H21 120.0 . . ?
C21 C22 C23 119.2(3) . . ?
C21 C22 H22 120.4 . . ?
C23 C22 H22 120.4 . . ?
C22 C23 C22 120.3(4) 4_565 . ?
C22 C23 H23 119.8 4_565 . ?
C22 C23 H23 119.8 . . ?

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
P1 P1 C1 C2 58.79(17) 6 . . . ?
P1 P1 C1 C2 -28.86(18) 4_565 . . . ?
P1 P1 C1 C6 -119.58(13) 6 . . . ?
P1 P1 C1 C6 152.77(12) 4_565 . . . ?
C6 C1 C2 C3 -3.1(3) . . . . ?
P1 C1 C2 C3 178.59(15) . . . . ?
C6 C1 C2 C7 176.30(17) . . . . ?
P1 C1 C2 C7 -2.0(3) . . . . ?
C1 C2 C3 C4 3.1(3) . . . . ?
C7 C2 C3 C4 -176.4(2) . . . . ?
C2 C3 C4 C5 -0.7(4) . . . . ?
C3 C4 C5 C6 -1.7(4) . . . . ?
C4 C5 C6 C1 1.6(3) . . . . ?
C4 C5 C6 C10 -179.0(2) . . . . ?
C2 C1 C6 C5 0.9(3) . . . . ?
P1 C1 C6 C5 179.38(16) . . . . ?
C2 C1 C6 C10 -178.5(2) . . . . ?
P1 C1 C6 C10 0.0(3) . . . . ?
C3 C2 C7 C9 -70.8(2) . . . . ?
C1 C2 C7 C9 109.7(2) . . . . ?
C3 C2 C7 C8 53.9(2) . . . . ?
C1 C2 C7 C8 -125.52(19) . . . . ?
C5 C6 C10 C11 -71.3(4) . . . . ?
C1 C6 C10 C11 108.1(3) . . . . ?
C5 C6 C10 C12 54.7(4) . . . . ?
C1 C6 C10 C12 -126.0(3) . . . . ?
C21 C20 C21 C22 -1.0(3) 4_565 . . . ?
C20 C21 C22 C23 1.9(6) . . . . ?
C21 C22 C23 C22 -1.0(3) . . . 4_565 ?

_refine_diff_density_max         0.257
_refine_diff_density_min         -0.193
_refine_diff_density_rms         0.039

####################################################################### 
# 
# 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_ax2141_DipPIMe4_cmpd_5
_database_code_depnum_ccdc_archive 'CCDC 2098829'
loop_
_audit_author_name
_audit_author_address
'Christian Hering-Junghans'
;Leibniz Institute for Catalysis Rostock
Germany
;
_audit_update_record             
;
2021-07-23 deposited with the CCDC.	2021-09-28 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7

#==============================================================================

# CHEMICAL DATA

_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H29 N2 P'
_chemical_formula_sum            'C19 H29 N2 P'
_chemical_formula_weight         316.41

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
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                   14.2549(15)
_cell_length_b                   9.7910(10)
_cell_length_c                   14.6252(15)
_cell_angle_alpha                90
_cell_angle_beta                 115.911(2)
_cell_angle_gamma                90
_cell_volume                     1836.0(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    6943
_cell_measurement_theta_min      2.59
_cell_measurement_theta_max      29.13

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.145
_exptl_crystal_F_000             688
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.450
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.150
_exptl_absorpt_coefficient_mu    0.149
_shelx_estimated_absorpt_T_min   0.936
_shelx_estimated_absorpt_T_max   0.978
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.936
_exptl_absorpt_correction_T_max  0.978
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_absorpt_special_details   ?

#==============================================================================

# EXPERIMENTAL DATA

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            21175
_diffrn_reflns_av_unetI/netI     0.0253
_diffrn_reflns_av_R_equivalents  0.0296
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       19
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         1.664
_diffrn_reflns_theta_max         29.192
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             4961
_reflns_number_gt                4003
_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       'APEX2 (Bruker, 2014)'
_computing_cell_refinement       'SAINT (Bruker, 2013)'
_computing_data_reduction        SAINT
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'ORTEP-3v2.01 (Farrugia, 1997)'
_computing_publication_material  'SHELXL-2014/7 (Sheldrick, 2014)'

#==============================================================================

# REFINEMENT DATA 

_refine_special_details          
;
 All H atoms 
 were positioned geometrically and refined using a riding model, with C---H = 
 0.98 (methyl groups), 0.99Å (methylene groups), 1.00Å (methine groups) or 
 0.95 Å (aryl CH) and with Uiso(H) = 1.5 times Ueq(C) 
 (methyl groups) or with Uiso(H) = 1.2 times Ueq(C) 
 (methylene  groups, aryl CH, methine groups). Torsion angles of all methyl 
 groups were allowed to refine.
 
 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 > 2σ(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     
'w=1/[σ²(Fo²)+(0.0569P)²+0.6139P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4961
_refine_ls_number_parameters     207
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0530
_refine_ls_R_factor_gt           0.0407
_refine_ls_wR_factor_ref         0.1118
_refine_ls_wR_factor_gt          0.1017
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_restrained_S_all      1.014
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

#==============================================================================

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

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
P1 P 0.33928(2) 0.34694(3) 0.56690(2) 0.02410(10) Uani 1 1 d . . . . .
N1 N 0.23535(8) 0.60722(10) 0.49146(8) 0.0222(2) Uani 1 1 d . . . . .
N2 N 0.40452(8) 0.60670(11) 0.55653(8) 0.0227(2) Uani 1 1 d . . . . .
C1 C 0.20649(9) 0.27431(11) 0.50225(9) 0.0203(2) Uani 1 1 d . . . . .
C2 C 0.16151(9) 0.21573(12) 0.56284(9) 0.0218(2) Uani 1 1 d . . . . .
C3 C 0.06163(10) 0.15991(13) 0.51551(10) 0.0260(3) Uani 1 1 d . . . . .
H3 H 0.0311 0.1220 0.5560 0.031 Uiso 1 1 calc R U . . .
C4 C 0.00600(10) 0.15868(13) 0.41059(10) 0.0276(3) Uani 1 1 d . . . . .
H4 H -0.0626 0.1222 0.3798 0.033 Uiso 1 1 calc R U . . .
C5 C 0.05057(9) 0.21064(13) 0.35089(10) 0.0252(3) Uani 1 1 d . . . . .
H5 H 0.0127 0.2077 0.2790 0.030 Uiso 1 1 calc R U . . .
C6 C 0.15057(9) 0.26756(12) 0.39484(9) 0.0217(2) Uani 1 1 d . . . . .
C7 C 0.22122(11) 0.21033(14) 0.67818(10) 0.0291(3) Uani 1 1 d . . . . .
H7 H 0.2654 0.2943 0.7004 0.035 Uiso 1 1 calc R U . . .
C8 C 0.15182(14) 0.20838(19) 0.73384(12) 0.0451(4) Uani 1 1 d . . . . .
H8A H 0.1012 0.2832 0.7088 0.068 Uiso 1 1 calc R U . . .
H8B H 0.1951 0.2197 0.8070 0.068 Uiso 1 1 calc R U . . .
H8C H 0.1147 0.1210 0.7213 0.068 Uiso 1 1 calc R U . . .
C9 C 0.29478(12) 0.08705(16) 0.70989(12) 0.0406(4) Uani 1 1 d . . . . .
H9A H 0.2538 0.0027 0.6892 0.061 Uiso 1 1 calc R U . . .
H9B H 0.3361 0.0873 0.7839 0.061 Uiso 1 1 calc R U . . .
H9C H 0.3416 0.0922 0.6769 0.061 Uiso 1 1 calc R U . . .
C10 C 0.19715(10) 0.31644(14) 0.32472(9) 0.0273(3) Uani 1 1 d . . . . .
H10 H 0.2532 0.3841 0.3629 0.033 Uiso 1 1 calc R U . . .
C11 C 0.24747(13) 0.19520(17) 0.29693(13) 0.0400(3) Uani 1 1 d . . . . .
H11A H 0.3019 0.1557 0.3590 0.060 Uiso 1 1 calc R U . . .
H11B H 0.2784 0.2264 0.2525 0.060 Uiso 1 1 calc R U . . .
H11C H 0.1943 0.1259 0.2615 0.060 Uiso 1 1 calc R U . . .
C12 C 0.11818(14) 0.3856(2) 0.22820(13) 0.0494(4) Uani 1 1 d . . . . .
H12A H 0.1538 0.4196 0.1886 0.074 Uiso 1 1 calc R U . . .
H12B H 0.0855 0.4622 0.2465 0.074 Uiso 1 1 calc R U . . .
H12C H 0.0645 0.3196 0.1875 0.074 Uiso 1 1 calc R U . . .
C13 C 0.32042(9) 0.52271(12) 0.53488(9) 0.0202(2) Uani 1 1 d . . . . .
C14 C 0.26757(10) 0.74228(12) 0.48675(9) 0.0243(2) Uani 1 1 d . . . . .
C15 C 0.37257(10) 0.74155(13) 0.52819(9) 0.0251(3) Uani 1 1 d . . . . .
C16 C 0.12906(10) 0.57232(14) 0.47331(12) 0.0326(3) Uani 1 1 d . . . . .
H16A H 0.0917 0.5340 0.4049 0.049 Uiso 1 1 calc R U . . .
H16B H 0.0931 0.6547 0.4792 0.049 Uiso 1 1 calc R U . . .
H16C H 0.1311 0.5048 0.5236 0.049 Uiso 1 1 calc R U . . .
C17 C 0.51163(10) 0.56168(15) 0.61412(11) 0.0305(3) Uani 1 1 d . . . . .
H17A H 0.5295 0.5633 0.6869 0.046 Uiso 1 1 calc R U . . .
H17B H 0.5585 0.6229 0.6006 0.046 Uiso 1 1 calc R U . . .
H17C H 0.5192 0.4685 0.5938 0.046 Uiso 1 1 calc R U . . .
C18 C 0.19202(12) 0.85667(14) 0.44327(12) 0.0357(3) Uani 1 1 d . . . . .
H18A H 0.1570 0.8743 0.4867 0.054 Uiso 1 1 calc R U . . .
H18B H 0.1400 0.8320 0.3749 0.054 Uiso 1 1 calc R U . . .
H18C H 0.2293 0.9390 0.4396 0.054 Uiso 1 1 calc R U . . .
C19 C 0.44853(12) 0.85414(15) 0.54639(12) 0.0370(3) Uani 1 1 d . . . . .
H19A H 0.4108 0.9400 0.5208 0.056 Uiso 1 1 calc R U . . .
H19B H 0.4915 0.8343 0.5109 0.056 Uiso 1 1 calc R U . . .
H19C H 0.4933 0.8624 0.6195 0.056 Uiso 1 1 calc R U . . .


#==============================================================================

# MOLECULAR GEOMETRY

_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 C13 1.7730(13) . ?
P1 C1 1.8490(12) . ?
N1 C13 1.3731(15) . ?
N1 C14 1.4114(16) . ?
N1 C16 1.4599(16) . ?
N2 C13 1.3718(15) . ?
N2 C15 1.3991(17) . ?
N2 C17 1.4530(16) . ?
C1 C6 1.4189(17) . ?
C1 C2 1.4219(16) . ?
C2 C3 1.3942(17) . ?
C2 C7 1.5225(17) . ?
C3 C4 1.3857(19) . ?
C3 H3 0.9500 . ?
C4 C5 1.3818(18) . ?
C4 H4 0.9500 . ?
C5 C6 1.3983(16) . ?
C5 H5 0.9500 . ?
C6 C10 1.5219(17) . ?
C7 C8 1.532(2) . ?
C7 C9 1.532(2) . ?
C7 H7 1.0000 . ?
C8 H8A 0.9800 . ?
C8 H8B 0.9800 . ?
C8 H8C 0.9800 . ?
C9 H9A 0.9800 . ?
C9 H9B 0.9800 . ?
C9 H9C 0.9800 . ?
C10 C12 1.527(2) . ?
C10 C11 1.531(2) . ?
C10 H10 1.0000 . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C14 C15 1.3472(18) . ?
C14 C18 1.4900(19) . ?
C15 C19 1.4854(18) . ?
C16 H16A 0.9800 . ?
C16 H16B 0.9800 . ?
C16 H16C 0.9800 . ?
C17 H17A 0.9800 . ?
C17 H17B 0.9800 . ?
C17 H17C 0.9800 . ?
C18 H18A 0.9800 . ?
C18 H18B 0.9800 . ?
C18 H18C 0.9800 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?

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
C13 P1 C1 103.60(5) . . ?
C13 N1 C14 110.28(10) . . ?
C13 N1 C16 125.43(10) . . ?
C14 N1 C16 122.98(10) . . ?
C13 N2 C15 111.03(10) . . ?
C13 N2 C17 122.88(11) . . ?
C15 N2 C17 125.56(10) . . ?
C6 C1 C2 118.89(10) . . ?
C6 C1 P1 122.57(9) . . ?
C2 C1 P1 118.43(9) . . ?
C3 C2 C1 119.30(11) . . ?
C3 C2 C7 119.46(11) . . ?
C1 C2 C7 121.23(11) . . ?
C4 C3 C2 121.28(11) . . ?
C4 C3 H3 119.4 . . ?
C2 C3 H3 119.4 . . ?
C5 C4 C3 119.86(11) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
C4 C5 C6 120.94(12) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C5 C6 C1 119.61(11) . . ?
C5 C6 C10 118.23(11) . . ?
C1 C6 C10 122.14(10) . . ?
C2 C7 C8 114.27(12) . . ?
C2 C7 C9 109.88(11) . . ?
C8 C7 C9 110.17(12) . . ?
C2 C7 H7 107.4 . . ?
C8 C7 H7 107.4 . . ?
C9 C7 H7 107.4 . . ?
C7 C8 H8A 109.5 . . ?
C7 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C7 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C7 C9 H9A 109.5 . . ?
C7 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C7 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C6 C10 C12 113.59(11) . . ?
C6 C10 C11 109.15(11) . . ?
C12 C10 C11 109.90(13) . . ?
C6 C10 H10 108.0 . . ?
C12 C10 H10 108.0 . . ?
C11 C10 H10 108.0 . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C10 C12 H12A 109.5 . . ?
C10 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C10 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N2 C13 N1 104.57(10) . . ?
N2 C13 P1 120.31(9) . . ?
N1 C13 P1 135.10(9) . . ?
C15 C14 N1 107.12(11) . . ?
C15 C14 C18 130.52(12) . . ?
N1 C14 C18 122.36(11) . . ?
C14 C15 N2 106.98(10) . . ?
C14 C15 C19 131.02(13) . . ?
N2 C15 C19 121.99(12) . . ?
N1 C16 H16A 109.5 . . ?
N1 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
N1 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
N2 C17 H17A 109.5 . . ?
N2 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
N2 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C14 C18 H18A 109.5 . . ?
C14 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C14 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C15 C19 H19A 109.5 . . ?
C15 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C15 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C13 P1 C1 C6 66.95(11) . . . . ?
C13 P1 C1 C2 -116.89(9) . . . . ?
C6 C1 C2 C3 -3.42(17) . . . . ?
P1 C1 C2 C3 -179.73(9) . . . . ?
C6 C1 C2 C7 175.34(11) . . . . ?
P1 C1 C2 C7 -0.96(15) . . . . ?
C1 C2 C3 C4 0.93(18) . . . . ?
C7 C2 C3 C4 -177.85(12) . . . . ?
C2 C3 C4 C5 1.5(2) . . . . ?
C3 C4 C5 C6 -1.4(2) . . . . ?
C4 C5 C6 C1 -1.11(19) . . . . ?
C4 C5 C6 C10 176.99(12) . . . . ?
C2 C1 C6 C5 3.52(17) . . . . ?
P1 C1 C6 C5 179.66(9) . . . . ?
C2 C1 C6 C10 -174.50(11) . . . . ?
P1 C1 C6 C10 1.64(16) . . . . ?
C3 C2 C7 C8 -28.15(17) . . . . ?
C1 C2 C7 C8 153.09(12) . . . . ?
C3 C2 C7 C9 96.28(14) . . . . ?
C1 C2 C7 C9 -82.48(15) . . . . ?
C5 C6 C10 C12 38.82(18) . . . . ?
C1 C6 C10 C12 -143.13(14) . . . . ?
C5 C6 C10 C11 -84.19(14) . . . . ?
C1 C6 C10 C11 93.86(14) . . . . ?
C15 N2 C13 N1 0.67(13) . . . . ?
C17 N2 C13 N1 172.76(11) . . . . ?
C15 N2 C13 P1 -178.01(8) . . . . ?
C17 N2 C13 P1 -5.93(16) . . . . ?
C14 N1 C13 N2 -0.04(13) . . . . ?
C16 N1 C13 N2 -167.28(12) . . . . ?
C14 N1 C13 P1 178.35(10) . . . . ?
C16 N1 C13 P1 11.1(2) . . . . ?
C1 P1 C13 N2 -169.87(9) . . . . ?
C1 P1 C13 N1 11.94(14) . . . . ?
C13 N1 C14 C15 -0.61(14) . . . . ?
C16 N1 C14 C15 167.00(12) . . . . ?
C13 N1 C14 C18 -179.96(12) . . . . ?
C16 N1 C14 C18 -12.36(19) . . . . ?
N1 C14 C15 N2 0.99(13) . . . . ?
C18 C14 C15 N2 -179.73(13) . . . . ?
N1 C14 C15 C19 -177.95(13) . . . . ?
C18 C14 C15 C19 1.3(2) . . . . ?
C13 N2 C15 C14 -1.07(14) . . . . ?
C17 N2 C15 C14 -172.90(11) . . . . ?
C13 N2 C15 C19 177.99(12) . . . . ?
C17 N2 C15 C19 6.16(19) . . . . ?

_refine_diff_density_max         0.423
_refine_diff_density_min         -0.169
_refine_diff_density_rms         0.050

