# Electronic Supplementary Material (ESI) for Inorganic Chemistry Frontiers.
# This journal is © the Partner Organisations 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_3a
_database_code_depnum_ccdc_archive 'CCDC 2077813'
loop_
_audit_author_name
_audit_author_address
'Lukasz Ponikiewski'
;Gdansk University of Technology
Poland
;
_audit_update_record             
;
2021-04-23 deposited with the CCDC.	2021-06-21 downloaded from the CCDC.
;

_audit_creation_date             2021-01-19T13:26:31-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'C21  H28  P2'
_chemical_formula_sum            'C21 H28 P2'
_chemical_formula_weight         342.37

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 2/c'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_Int_Tables_number      15
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   15.2838(7)
_cell_length_b                   10.1380(4)
_cell_length_c                   26.3114(11)
_cell_angle_alpha                90
_cell_angle_beta                 101.444(4)
_cell_angle_gamma                90
_cell_volume                     3995.8(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    17243
_cell_measurement_theta_min      3.43
_cell_measurement_theta_max      67.78
_cell_measurement_wavelength     1.54186

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.17
_exptl_crystal_density_diffrn    1.138
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1472

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    1.935
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   
;
STOE X-Red32, absorption correction by Gaussian integration, analogous to
P. Coppens, "The Evaluation of Absorption and Extinction in Single-Crystal
Structure Analysis", published in
F. R. Ahmed (Editor), "Crystallographic Computing",
Munksgaard, Copenhagen (1970), 255 - 270
;
_exptl_absorpt_correction_T_min  0.7391
_exptl_absorpt_correction_T_max  0.8352
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-1 1 -5 0.1020
1 -1 5 0.0700
-2 -2 -1 0.0490
4 4 1 0.0860
1 2 -3 0.0890
0 3 5 0.0540
-5 -2 -2 0.0640
-1 -3 -5 0.0640
5 0 -3 0.0750

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     1.54186
_diffrn_radiation_type           CuK\a
_diffrn_radiation_probe          x-ray
_diffrn_standards_number         0
_diffrn_measurement_device       '2-circle diffractometer'
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_type            'STOE Imaging Plate'
_diffrn_detector_area_resol_mean 6.67
_diffrn_source                   'GeniX Cu, 0.05 x 0.05 mm2 microfocus'
_diffrn_source_type              ?
_diffrn_source_target            ?
_diffrn_source_voltage           50
_diffrn_source_current           0.600
_diffrn_source_power             0.030
_diffrn_radiation_monochromator  'parabolic x-ray mirror'
_diffrn_radiation_polarisn_norm  270
_diffrn_radiation_collimation    '0.6 mm diameter'
_diffrn_measurement_method       'rotation method, ω scans'
_diffrn_measurement_details      
; 791 frames, detector distance = 45 mm
;
_diffrn_reflns_av_R_equivalents  0.029
_diffrn_reflns_av_unetI/netI     0.0257
_diffrn_reflns_number            10361
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_theta_min         3.428
_diffrn_reflns_theta_max         67.589
_diffrn_reflns_theta_full        67.589
_diffrn_measured_fraction_theta_full 0.972
_diffrn_measured_fraction_theta_max 0.972
_diffrn_reflns_Laue_measured_fraction_full 0.972
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_point_group_measured_fraction_full 0.972
_diffrn_reflns_point_group_measured_fraction_max 0.972
_reflns_Friedel_coverage         0
_reflns_number_total             3492
_reflns_number_gt                2974
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       
;
X-Area WinXpose 2.0.22.0 (STOE, 2016)
;
_computing_cell_refinement       
;
X-Area Recipe 1.33.0.0 (STOE, 2015)
;
_computing_data_reduction        
;
X-Area Integrate 1.72.0.0 (STOE, 2018)
X-Area X-Red32 1.63.4.0 (STOE, 2017) 
;
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0548P)²+5.4644P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3492
_refine_ls_number_parameters     214
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0496
_refine_ls_R_factor_gt           0.041
_refine_ls_wR_factor_ref         0.1107
_refine_ls_wR_factor_gt          0.1054
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.236
_refine_diff_density_min         -0.365
_refine_diff_density_rms         0.05

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
C1 C 0.40746(13) 0.5298(2) 0.66125(7) 0.0256(4) Uani 1 1 d . . . . .
C2 C 0.37834(13) 0.4443(2) 0.70069(7) 0.0257(4) Uani 1 1 d . . . . .
C3 C 0.33533(14) 0.4960(2) 0.73871(8) 0.0319(5) Uani 1 1 d . . . . .
H3 H 0.322614 0.587676 0.738725 0.038 Uiso 1 1 calc R U . . .
C4 C 0.31113(15) 0.4160(2) 0.77611(9) 0.0374(5) Uani 1 1 d . . . . .
H4 H 0.281971 0.452975 0.801479 0.045 Uiso 1 1 calc R U . . .
C5 C 0.32930(16) 0.2819(2) 0.77675(9) 0.0382(5) Uani 1 1 d . . . . .
H5 H 0.313507 0.226849 0.80274 0.046 Uiso 1 1 calc R U . . .
C6 C 0.37039(17) 0.2294(2) 0.73937(9) 0.0397(6) Uani 1 1 d . . . . .
H6 H 0.382271 0.137439 0.739381 0.048 Uiso 1 1 calc R U . . .
C7 C 0.39468(15) 0.3090(2) 0.70172(8) 0.0331(5) Uani 1 1 d . . . . .
H7 H 0.422918 0.270774 0.676187 0.04 Uiso 1 1 calc R U . . .
C8 C 0.42119(12) 0.46195(19) 0.61299(7) 0.0239(4) Uani 1 1 d . . . . .
C9 C 0.50517(15) 0.4322(2) 0.60466(11) 0.0464(6) Uani 1 1 d . . . . .
H9 H 0.556061 0.454967 0.6302 0.056 Uiso 1 1 calc R U . . .
C10 C 0.51656(17) 0.3697(3) 0.55976(12) 0.0550(8) Uani 1 1 d . . . . .
H10 H 0.575095 0.34839 0.555303 0.066 Uiso 1 1 calc R U . . .
C11 C 0.44503(17) 0.3380(2) 0.52162(9) 0.0431(6) Uani 1 1 d . . . . .
H11 H 0.453327 0.29792 0.490289 0.052 Uiso 1 1 calc R U . . .
C12 C 0.36107(17) 0.3656(3) 0.52972(10) 0.0517(7) Uani 1 1 d . . . . .
H12 H 0.310472 0.342483 0.504017 0.062 Uiso 1 1 calc R U . . .
C13 C 0.34911(15) 0.4267(3) 0.57499(9) 0.0441(6) Uani 1 1 d . . . . .
H13 H 0.290358 0.444607 0.579927 0.053 Uiso 1 1 calc R U . . .
C14 C 0.56845(13) 0.8626(2) 0.63648(8) 0.0290(5) Uani 1 1 d . . . . .
C15 C 0.56966(16) 0.9272(2) 0.68934(9) 0.0390(5) Uani 1 1 d . . . . .
H15A H 0.628668 0.965589 0.702455 0.058 Uiso 1 1 calc R U . . .
H15B H 0.556784 0.860534 0.713816 0.058 Uiso 1 1 calc R U . . .
H15C H 0.524293 0.996754 0.685528 0.058 Uiso 1 1 calc R U . . .
C16 C 0.63993(16) 0.7541(3) 0.64415(10) 0.0461(6) Uani 1 1 d . . . . .
H16A H 0.643424 0.715341 0.610491 0.069 Uiso 1 1 calc R U . . .
H16B H 0.624093 0.685466 0.666964 0.069 Uiso 1 1 calc R U . . .
H16C H 0.697911 0.792184 0.659904 0.069 Uiso 1 1 calc R U . . .
C17 C 0.59351(15) 0.9660(2) 0.59947(9) 0.0382(5) Uani 1 1 d . . . . .
H17A H 0.550191 1.038422 0.595422 0.057 Uiso 1 1 calc R U . . .
H17B H 0.593088 0.925431 0.565617 0.057 Uiso 1 1 calc R U . . .
H17C H 0.653279 1.000432 0.613663 0.057 Uiso 1 1 calc R U . . .
C18 C 0.36835(14) 0.8954(2) 0.58369(8) 0.0333(5) Uani 1 1 d . . . . .
C19 C 0.28227(16) 0.8131(3) 0.57533(11) 0.0555(7) Uani 1 1 d . . . . .
H19A H 0.232363 0.866131 0.556815 0.083 Uiso 1 1 calc R U . . .
H19B H 0.270062 0.786142 0.609002 0.083 Uiso 1 1 calc R U . . .
H19C H 0.289482 0.734603 0.554824 0.083 Uiso 1 1 calc R U . . .
C20 C 0.37818(16) 0.9505(2) 0.53062(9) 0.0409(6) Uani 1 1 d . . . . .
H20A H 0.325798 1.004206 0.516207 0.061 Uiso 1 1 calc R U . . .
H20B H 0.382966 0.877309 0.507004 0.061 Uiso 1 1 calc R U . . .
H20C H 0.432036 1.005164 0.534841 0.061 Uiso 1 1 calc R U . . .
C21 C 0.36151(18) 1.0096(3) 0.62086(10) 0.0496(7) Uani 1 1 d . . . . .
H21A H 0.413186 1.067987 0.622814 0.074 Uiso 1 1 calc R U . . .
H21B H 0.360381 0.97446 0.655418 0.074 Uiso 1 1 calc R U . . .
H21C H 0.306595 1.05945 0.608119 0.074 Uiso 1 1 calc R U . . .
P1 P 0.42555(4) 0.69208(5) 0.67515(2) 0.03604(18) Uani 1 1 d . . . . .
P2 P 0.46276(3) 0.77346(5) 0.60414(2) 0.02438(15) Uani 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   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
C1 C2 1.486(3) . ?
C1 C8 1.495(3) . ?
C1 P1 1.696(2) . ?
C2 C7 1.394(3) . ?
C2 C3 1.403(3) . ?
C3 C4 1.381(3) . ?
C3 H3 0.95 . ?
C4 C5 1.388(3) . ?
C4 H4 0.95 . ?
C5 C6 1.375(3) . ?
C5 H5 0.95 . ?
C6 C7 1.384(3) . ?
C6 H6 0.95 . ?
C7 H7 0.95 . ?
C8 C9 1.378(3) . ?
C8 C13 1.380(3) . ?
C9 C10 1.382(4) . ?
C9 H9 0.95 . ?
C10 C11 1.367(4) . ?
C10 H10 0.95 . ?
C11 C12 1.371(3) . ?
C11 H11 0.95 . ?
C12 C13 1.387(3) . ?
C12 H12 0.95 . ?
C13 H13 0.95 . ?
C14 C17 1.531(3) . ?
C14 C15 1.534(3) . ?
C14 C16 1.535(3) . ?
C14 P2 1.899(2) . ?
C15 H15A 0.98 . ?
C15 H15B 0.98 . ?
C15 H15C 0.98 . ?
C16 H16A 0.98 . ?
C16 H16B 0.98 . ?
C16 H16C 0.98 . ?
C17 H17A 0.98 . ?
C17 H17B 0.98 . ?
C17 H17C 0.98 . ?
C18 C21 1.532(3) . ?
C18 C19 1.536(3) . ?
C18 C20 1.539(3) . ?
C18 P2 1.895(2) . ?
C19 H19A 0.98 . ?
C19 H19B 0.98 . ?
C19 H19C 0.98 . ?
C20 H20A 0.98 . ?
C20 H20B 0.98 . ?
C20 H20C 0.98 . ?
C21 H21A 0.98 . ?
C21 H21B 0.98 . ?
C21 H21C 0.98 . ?
P1 P2 2.2173(7) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C8 115.90(17) . . ?
C2 C1 P1 118.27(15) . . ?
C8 C1 P1 125.79(14) . . ?
C7 C2 C3 117.47(19) . . ?
C7 C2 C1 120.67(19) . . ?
C3 C2 C1 121.85(18) . . ?
C4 C3 C2 121.3(2) . . ?
C4 C3 H3 119.4 . . ?
C2 C3 H3 119.4 . . ?
C3 C4 C5 120.2(2) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C6 C5 C4 119.3(2) . . ?
C6 C5 H5 120.4 . . ?
C4 C5 H5 120.4 . . ?
C5 C6 C7 120.8(2) . . ?
C5 C6 H6 119.6 . . ?
C7 C6 H6 119.6 . . ?
C6 C7 C2 121.0(2) . . ?
C6 C7 H7 119.5 . . ?
C2 C7 H7 119.5 . . ?
C9 C8 C13 117.6(2) . . ?
C9 C8 C1 121.87(18) . . ?
C13 C8 C1 120.54(18) . . ?
C8 C9 C10 121.1(2) . . ?
C8 C9 H9 119.5 . . ?
C10 C9 H9 119.5 . . ?
C11 C10 C9 121.1(2) . . ?
C11 C10 H10 119.4 . . ?
C9 C10 H10 119.4 . . ?
C10 C11 C12 118.4(2) . . ?
C10 C11 H11 120.8 . . ?
C12 C11 H11 120.8 . . ?
C11 C12 C13 120.8(2) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 H12 119.6 . . ?
C8 C13 C12 121.1(2) . . ?
C8 C13 H13 119.5 . . ?
C12 C13 H13 119.5 . . ?
C17 C14 C15 108.96(18) . . ?
C17 C14 C16 108.25(18) . . ?
C15 C14 C16 107.85(18) . . ?
C17 C14 P2 109.80(14) . . ?
C15 C14 P2 117.76(14) . . ?
C16 C14 P2 103.76(15) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C14 C17 H17A 109.5 . . ?
C14 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C14 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C21 C18 C19 109.7(2) . . ?
C21 C18 C20 109.6(2) . . ?
C19 C18 C20 107.59(19) . . ?
C21 C18 P2 117.14(16) . . ?
C19 C18 P2 105.57(17) . . ?
C20 C18 P2 106.77(14) . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C18 C20 H20A 109.5 . . ?
C18 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C18 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C18 C21 H21A 109.5 . . ?
C18 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C18 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C1 P1 P2 103.73(7) . . ?
C18 P2 C14 110.42(10) . . ?
C18 P2 P1 100.01(7) . . ?
C14 P2 P1 97.88(7) . . ?

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
C8 C1 C2 C7 22.7(3) . . . . ?
P1 C1 C2 C7 -155.28(17) . . . . ?
C8 C1 C2 C3 -158.61(18) . . . . ?
P1 C1 C2 C3 23.4(3) . . . . ?
C7 C2 C3 C4 0.8(3) . . . . ?
C1 C2 C3 C4 -177.95(19) . . . . ?
C2 C3 C4 C5 0.1(3) . . . . ?
C3 C4 C5 C6 -0.9(3) . . . . ?
C4 C5 C6 C7 0.8(4) . . . . ?
C5 C6 C7 C2 0.1(3) . . . . ?
C3 C2 C7 C6 -0.9(3) . . . . ?
C1 C2 C7 C6 177.86(19) . . . . ?
C2 C1 C8 C9 -102.9(2) . . . . ?
P1 C1 C8 C9 74.9(3) . . . . ?
C2 C1 C8 C13 77.0(3) . . . . ?
P1 C1 C8 C13 -105.2(2) . . . . ?
C13 C8 C9 C10 0.2(4) . . . . ?
C1 C8 C9 C10 -179.9(2) . . . . ?
C8 C9 C10 C11 1.5(4) . . . . ?
C9 C10 C11 C12 -2.3(4) . . . . ?
C10 C11 C12 C13 1.4(4) . . . . ?
C9 C8 C13 C12 -1.1(4) . . . . ?
C1 C8 C13 C12 179.0(2) . . . . ?
C11 C12 C13 C8 0.3(4) . . . . ?
C2 C1 P1 P2 -178.36(13) . . . . ?
C8 C1 P1 P2 3.91(18) . . . . ?
C21 C18 P2 C14 -39.3(2) . . . . ?
C19 C18 P2 C14 -161.72(15) . . . . ?
C20 C18 P2 C14 83.97(16) . . . . ?
C21 C18 P2 P1 63.04(18) . . . . ?
C19 C18 P2 P1 -59.35(16) . . . . ?
C20 C18 P2 P1 -173.66(14) . . . . ?
C17 C14 P2 C18 -57.54(17) . . . . ?
C15 C14 P2 C18 67.89(18) . . . . ?
C16 C14 P2 C18 -173.06(14) . . . . ?
C17 C14 P2 P1 -161.35(14) . . . . ?
C15 C14 P2 P1 -35.92(17) . . . . ?
C16 C14 P2 P1 83.12(14) . . . . ?



# END of CIF
####################################################################### 
# 
# 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_3c
_database_code_depnum_ccdc_archive 'CCDC 2077814'
loop_
_audit_author_name
_audit_author_address
'Lukasz Ponikiewski'
;Gdansk University of Technology
Poland
;
_audit_update_record             
;
2021-04-23 deposited with the CCDC.	2021-06-21 downloaded from the CCDC.
;

_audit_creation_date             2021-01-19T12:53:25-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'C22  H27  N1  P2'
_chemical_formula_sum            'C22 H27 N P2'
_chemical_formula_weight         367.38

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P b c n'
_symmetry_space_group_name_Hall  '-P 2n 2ab'
_symmetry_Int_Tables_number      60
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y+1/2, z+1/2'
'-x, y, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y-1/2, -z-1/2'
'x, -y, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   24.4705(11)
_cell_length_b                   9.0836(3)
_cell_length_c                   18.7680(7)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     4171.8(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    17492
_cell_measurement_theta_min      3.61
_cell_measurement_theta_max      65.20
_cell_measurement_wavelength     1.54186

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       needle
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.14
_exptl_crystal_density_diffrn    1.17
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1568

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    1.904
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   
;
STOE X-Red32, absorption correction by Gaussian integration, analogous to
P. Coppens, "The Evaluation of Absorption and Extinction in Single-Crystal
Structure Analysis", published in
F. R. Ahmed (Editor), "Crystallographic Computing",
Munksgaard, Copenhagen (1970), 255 - 270
;
_exptl_absorpt_correction_T_min  0.6623
_exptl_absorpt_correction_T_max  0.8610
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-3 -6 -1 0.0490
4 4 -1 0.0820
1 6 2 0.0790
1 -3 -2 0.1290
-2 3 3 0.1230
-1 1 -5 0.0160
1 -1 4 0.0800
-1 -2 7 0.1200

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     1.54186
_diffrn_radiation_type           CuK\a
_diffrn_radiation_probe          x-ray
_diffrn_standards_number         0
_diffrn_measurement_device       '2-circle diffractometer'
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_type            'STOE Imaging Plate'
_diffrn_detector_area_resol_mean 6.67
_diffrn_source                   'GeniX Cu, 0.05 x 0.05 mm2 microfocus'
_diffrn_source_type              ?
_diffrn_source_target            ?
_diffrn_source_voltage           50
_diffrn_source_current           0.600
_diffrn_source_power             0.030
_diffrn_radiation_monochromator  'parabolic x-ray mirror'
_diffrn_radiation_polarisn_norm  270
_diffrn_radiation_collimation    '0.6 mm diameter'
_diffrn_measurement_method       'rotation method, ω scans'
_diffrn_measurement_details      
; 626 frames, detector distance = 45 mm
;
_diffrn_reflns_av_R_equivalents  0.0545
_diffrn_reflns_av_unetI/netI     0.0401
_diffrn_reflns_number            19563
_diffrn_reflns_limit_h_min       -28
_diffrn_reflns_limit_h_max       24
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         3.613
_diffrn_reflns_theta_max         66.969
_diffrn_reflns_theta_full        66.969
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_reflns_Laue_measured_fraction_full 0.986
_diffrn_reflns_Laue_measured_fraction_max 0.986
_diffrn_reflns_point_group_measured_fraction_full 0.986
_diffrn_reflns_point_group_measured_fraction_max 0.986
_reflns_Friedel_coverage         0
_reflns_number_total             3675
_reflns_number_gt                2534
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       
;
X-Area WinXpose 2.0.22.0 (STOE, 2016)
;
_computing_cell_refinement       
;
X-Area Recipe 1.33.0.0 (STOE, 2015)
;
_computing_data_reduction        
;
X-Area Integrate 1.72.0.0 (STOE, 2018)
X-Area X-Red32 1.63.4.0 (STOE, 2017) 
;
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0921P)²+8.8572P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/1 (Sheldrick 2018)'
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_coef       0.0014(2)
_refine_ls_number_reflns         3675
_refine_ls_number_parameters     233
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.1064
_refine_ls_R_factor_gt           0.0686
_refine_ls_wR_factor_ref         0.209
_refine_ls_wR_factor_gt          0.1708
_refine_ls_goodness_of_fit_ref   1.089
_refine_ls_restrained_S_all      1.089
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.435
_refine_diff_density_min         -0.467
_refine_diff_density_rms         0.085

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
C1 C 0.41591(16) 0.4951(5) 0.6140(2) 0.0343(9) Uani 1 1 d . . . . .
C2 C 0.36109(16) 0.5034(5) 0.5777(2) 0.0339(9) Uani 1 1 d . . . . .
C3 C 0.34755(17) 0.4040(5) 0.5242(2) 0.0368(10) Uani 1 1 d . . . . .
H3 H 0.373076 0.330226 0.510775 0.044 Uiso 1 1 calc R U . . .
C4 C 0.29718(17) 0.4110(5) 0.4902(2) 0.0377(10) Uani 1 1 d . . . . .
H4 H 0.288654 0.343701 0.453133 0.045 Uiso 1 1 calc R U . . .
C5 C 0.25940(16) 0.5167(5) 0.5107(2) 0.0382(10) Uani 1 1 d . . . . .
C6 C 0.27206(19) 0.6164(5) 0.5653(2) 0.0454(11) Uani 1 1 d . . . . .
H6 H 0.245931 0.687087 0.580544 0.054 Uiso 1 1 calc R U . . .
C7 C 0.32326(18) 0.6104(5) 0.5967(2) 0.0407(10) Uani 1 1 d . . . . .
H7 H 0.332696 0.680982 0.63193 0.049 Uiso 1 1 calc R U . . .
C8 C 0.20686(19) 0.5228(5) 0.4760(2) 0.0452(11) Uani 1 1 d . . . . .
C9 C 0.45645(16) 0.6050(5) 0.5902(2) 0.0352(9) Uani 1 1 d . . . . .
C10 C 0.45058(19) 0.6803(5) 0.5251(2) 0.0468(12) Uani 1 1 d . . . . .
H10 H 0.419484 0.660469 0.496412 0.056 Uiso 1 1 calc R U . . .
C11 C 0.48818(19) 0.7815(6) 0.5017(3) 0.0520(13) Uani 1 1 d . . . . .
H11 H 0.483015 0.829612 0.457244 0.062 Uiso 1 1 calc R U . . .
C12 C 0.53345(19) 0.8134(5) 0.5427(3) 0.0484(12) Uani 1 1 d . . . . .
H12 H 0.559313 0.88432 0.526955 0.058 Uiso 1 1 calc R U . . .
C13 C 0.54087(19) 0.7413(5) 0.6068(3) 0.0511(12) Uani 1 1 d . . . . .
H13 H 0.572275 0.761652 0.634892 0.061 Uiso 1 1 calc R U . . .
C14 C 0.50273(18) 0.6393(5) 0.6304(2) 0.0439(11) Uani 1 1 d . . . . .
H14 H 0.508217 0.591816 0.674966 0.053 Uiso 1 1 calc R U . . .
C15 C 0.34039(18) 0.3399(5) 0.7925(2) 0.0402(10) Uani 1 1 d . . . . .
C16 C 0.3278(2) 0.5025(5) 0.7785(3) 0.0567(13) Uani 1 1 d . . . . .
H16A H 0.299159 0.51038 0.742284 0.085 Uiso 1 1 calc R U . . .
H16B H 0.360954 0.552073 0.761569 0.085 Uiso 1 1 calc R U . . .
H16C H 0.315399 0.549076 0.822731 0.085 Uiso 1 1 calc R U . . .
C17 C 0.3852(2) 0.3297(7) 0.8491(3) 0.0648(15) Uani 1 1 d . . . . .
H17A H 0.374436 0.386815 0.891091 0.097 Uiso 1 1 calc R U . . .
H17B H 0.419399 0.36929 0.829756 0.097 Uiso 1 1 calc R U . . .
H17C H 0.39055 0.226513 0.862631 0.097 Uiso 1 1 calc R U . . .
C18 C 0.2883(2) 0.2672(5) 0.8215(3) 0.0513(12) Uani 1 1 d . . . . .
H18A H 0.296447 0.165684 0.835699 0.077 Uiso 1 1 calc R U . . .
H18B H 0.260179 0.266875 0.784356 0.077 Uiso 1 1 calc R U . . .
H18C H 0.275153 0.322517 0.86287 0.077 Uiso 1 1 calc R U . . .
C19 C 0.3815(2) 0.0628(5) 0.7094(3) 0.0495(12) Uani 1 1 d . . . . .
C20 C 0.4265(3) 0.0380(7) 0.7660(4) 0.088(2) Uani 1 1 d . . . A 1
H20A H 0.410147 0.040723 0.813695 0.131 Uiso 1 1 calc R U . A 1
H20B H 0.454098 0.115706 0.762023 0.131 Uiso 1 1 calc R U . A 1
H20C H 0.443687 -0.058052 0.75826 0.131 Uiso 1 1 calc R U . A 1
C21 C 0.3346(2) -0.0404(6) 0.7276(3) 0.0661(16) Uani 1 1 d . . . B 1
H21A H 0.347634 -0.142396 0.726564 0.099 Uiso 1 1 calc R U . B 1
H21B H 0.305198 -0.027998 0.692745 0.099 Uiso 1 1 calc R U . B 1
H21C H 0.320836 -0.017275 0.775378 0.099 Uiso 1 1 calc R U . B 1
C22 C 0.4030(3) 0.0238(7) 0.6356(3) 0.089(2) Uani 1 1 d . . . C 1
H22A H 0.434911 0.085095 0.624685 0.133 Uiso 1 1 calc R U . C 1
H22B H 0.374417 0.041523 0.600089 0.133 Uiso 1 1 calc R U . C 1
H22C H 0.413601 -0.080211 0.634575 0.133 Uiso 1 1 calc R U . C 1
N1 N 0.16556(19) 0.5311(5) 0.4470(3) 0.0668(13) Uani 1 1 d . . . D 1
P1 P 0.43282(5) 0.37084(14) 0.67756(6) 0.0429(4) Uani 1 1 d . . . E 1
P2 P 0.35435(4) 0.25758(12) 0.70080(6) 0.0365(3) Uani 1 1 d . . . E 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
C1 C9 1.476(6) . ?
C1 C2 1.506(5) . ?
C1 P1 1.694(4) . ?
C2 C7 1.388(6) . ?
C2 C3 1.391(6) . ?
C3 C4 1.389(6) . ?
C3 H3 0.95 . ?
C4 C5 1.387(6) . ?
C4 H4 0.95 . ?
C5 C6 1.402(6) . ?
C5 C8 1.443(6) . ?
C6 C7 1.385(6) . ?
C6 H6 0.95 . ?
C7 H7 0.95 . ?
C8 N1 1.150(6) . ?
C9 C14 1.397(6) . ?
C9 C10 1.407(6) . ?
C10 C11 1.373(6) . ?
C10 H10 0.95 . ?
C11 C12 1.379(7) . ?
C11 H11 0.95 . ?
C12 C13 1.383(7) . ?
C12 H12 0.95 . ?
C13 C14 1.388(6) . ?
C13 H13 0.95 . ?
C14 H14 0.95 . ?
C15 C17 1.529(6) . ?
C15 C16 1.532(7) . ?
C15 C18 1.534(6) . ?
C15 P2 1.908(4) . ?
C16 H16A 0.98 . ?
C16 H16B 0.98 . ?
C16 H16C 0.98 . ?
C17 H17A 0.98 . ?
C17 H17B 0.98 . ?
C17 H17C 0.98 . ?
C18 H18A 0.98 . ?
C18 H18B 0.98 . ?
C18 H18C 0.98 . ?
C19 C21 1.520(7) . ?
C19 C22 1.524(7) . ?
C19 C20 1.546(8) . ?
C19 P2 1.897(5) . ?
C20 H20A 0.98 . ?
C20 H20B 0.98 . ?
C20 H20C 0.98 . ?
C21 H21A 0.98 . ?
C21 H21B 0.98 . ?
C21 H21C 0.98 . ?
C22 H22A 0.98 . ?
C22 H22B 0.98 . ?
C22 H22C 0.98 . ?
P1 P2 2.2215(15) . ?

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
C9 C1 C2 115.3(4) . . ?
C9 C1 P1 120.0(3) . . ?
C2 C1 P1 124.7(3) . . ?
C7 C2 C3 118.7(4) . . ?
C7 C2 C1 120.9(4) . . ?
C3 C2 C1 120.4(4) . . ?
C4 C3 C2 120.9(4) . . ?
C4 C3 H3 119.6 . . ?
C2 C3 H3 119.6 . . ?
C5 C4 C3 119.7(4) . . ?
C5 C4 H4 120.1 . . ?
C3 C4 H4 120.1 . . ?
C4 C5 C6 120.1(4) . . ?
C4 C5 C8 119.7(4) . . ?
C6 C5 C8 120.2(4) . . ?
C7 C6 C5 119.0(4) . . ?
C7 C6 H6 120.5 . . ?
C5 C6 H6 120.5 . . ?
C6 C7 C2 121.5(4) . . ?
C6 C7 H7 119.3 . . ?
C2 C7 H7 119.3 . . ?
N1 C8 C5 178.0(6) . . ?
C14 C9 C10 116.3(4) . . ?
C14 C9 C1 122.1(4) . . ?
C10 C9 C1 121.5(4) . . ?
C11 C10 C9 122.4(4) . . ?
C11 C10 H10 118.8 . . ?
C9 C10 H10 118.8 . . ?
C10 C11 C12 120.0(5) . . ?
C10 C11 H11 120 . . ?
C12 C11 H11 120 . . ?
C11 C12 C13 119.4(4) . . ?
C11 C12 H12 120.3 . . ?
C13 C12 H12 120.3 . . ?
C12 C13 C14 120.4(5) . . ?
C12 C13 H13 119.8 . . ?
C14 C13 H13 119.8 . . ?
C13 C14 C9 121.4(4) . . ?
C13 C14 H14 119.3 . . ?
C9 C14 H14 119.3 . . ?
C17 C15 C16 108.7(4) . . ?
C17 C15 C18 108.9(4) . . ?
C16 C15 C18 108.0(4) . . ?
C17 C15 P2 118.3(4) . . ?
C16 C15 P2 105.0(3) . . ?
C18 C15 P2 107.4(3) . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C15 C17 H17A 109.5 . . ?
C15 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C15 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C15 C18 H18A 109.5 . . ?
C15 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C15 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C21 C19 C22 108.8(5) . . ?
C21 C19 C20 107.0(5) . . ?
C22 C19 C20 110.2(5) . . ?
C21 C19 P2 109.3(4) . . ?
C22 C19 P2 105.1(4) . . ?
C20 C19 P2 116.4(4) . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C19 C21 H21A 109.5 . . ?
C19 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C19 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C19 C22 H22A 109.5 . . ?
C19 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C19 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C1 P1 P2 103.64(14) . . ?
C19 P2 C15 110.6(2) . . ?
C19 P2 P1 98.40(15) . . ?
C15 P2 P1 98.66(15) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C9 C1 C2 C7 -77.6(5) . . . . ?
P1 C1 C2 C7 102.8(5) . . . . ?
C9 C1 C2 C3 102.2(5) . . . . ?
P1 C1 C2 C3 -77.4(5) . . . . ?
C7 C2 C3 C4 0.0(6) . . . . ?
C1 C2 C3 C4 -179.7(4) . . . . ?
C2 C3 C4 C5 -1.2(6) . . . . ?
C3 C4 C5 C6 0.3(7) . . . . ?
C3 C4 C5 C8 -179.3(4) . . . . ?
C4 C5 C6 C7 2.0(7) . . . . ?
C8 C5 C6 C7 -178.5(4) . . . . ?
C5 C6 C7 C2 -3.3(7) . . . . ?
C3 C2 C7 C6 2.3(7) . . . . ?
C1 C2 C7 C6 -178.0(4) . . . . ?
C2 C1 C9 C14 162.0(4) . . . . ?
P1 C1 C9 C14 -18.4(6) . . . . ?
C2 C1 C9 C10 -18.4(6) . . . . ?
P1 C1 C9 C10 161.2(4) . . . . ?
C14 C9 C10 C11 0.4(7) . . . . ?
C1 C9 C10 C11 -179.2(4) . . . . ?
C9 C10 C11 C12 -0.6(8) . . . . ?
C10 C11 C12 C13 0.8(8) . . . . ?
C11 C12 C13 C14 -1.0(7) . . . . ?
C12 C13 C14 C9 0.9(7) . . . . ?
C10 C9 C14 C13 -0.6(7) . . . . ?
C1 C9 C14 C13 179.0(4) . . . . ?
C9 C1 P1 P2 172.9(3) . . . . ?
C2 C1 P1 P2 -7.5(4) . . . . ?
C21 C19 P2 C15 76.1(4) . . . . ?
C22 C19 P2 C15 -167.3(4) . . . . ?
C20 C19 P2 C15 -45.2(5) . . . . ?
C21 C19 P2 P1 178.7(3) . . . . ?
C22 C19 P2 P1 -64.7(4) . . . . ?
C20 C19 P2 P1 57.4(4) . . . . ?



# END of CIF
####################################################################### 
# 
# 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_4e
_database_code_depnum_ccdc_archive 'CCDC 2077818'
loop_
_audit_author_name
_audit_author_address
'Lukasz Ponikiewski'
;Gdansk University of Technology
Poland
;
_audit_update_record             
;
2021-04-23 deposited with the CCDC.	2021-06-21 downloaded from the CCDC.
;

_audit_creation_date             2021-01-20T15:19:29-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'C21 H28 P2'
_chemical_formula_sum            'C21 H28 P2'
_chemical_formula_weight         342.37

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'I 2/a'
_symmetry_space_group_name_Hall  '-I 2ya'
_symmetry_Int_Tables_number      15
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'

_cell_length_a                   23.6882(16)
_cell_length_b                   5.9485(2)
_cell_length_c                   29.8384(19)
_cell_angle_alpha                90
_cell_angle_beta                 111.433(5)
_cell_angle_gamma                90
_cell_volume                     3913.7(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    6984
_cell_measurement_theta_min      2.74
_cell_measurement_theta_max      29.34
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       needle
_exptl_crystal_colour            orange
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.13
_exptl_crystal_density_diffrn    1.162
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1472

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.221
_exptl_absorpt_correction_type   none
_shelx_estimated_absorpt_T_min   0.955
_shelx_estimated_absorpt_T_max   0.972

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_standards_number         0
_diffrn_measurement_device       '2-circle diffractometer'
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_type            'STOE Imaging Plate'
_diffrn_detector_area_resol_mean 6.67
_diffrn_source                   'GeniX Mo, 0.05 x 0.05 mm2 microfocus'
_diffrn_source_type              ?
_diffrn_source_target            ?
_diffrn_source_voltage           50
_diffrn_source_current           1.000
_diffrn_source_power             0.050
_diffrn_radiation_monochromator  'parabolic x-ray mirror'
_diffrn_radiation_polarisn_norm  270
_diffrn_radiation_collimation    '0.6 mm diameter'
_diffrn_measurement_method       'rotation method, ω scans'
_diffrn_measurement_details      
; 197 frames, detector distance = 100 mm
;
_diffrn_reflns_av_unetI/netI     0.086
_diffrn_reflns_number            4461
_diffrn_reflns_limit_h_min       -31
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -38
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_theta_min         2.747
_diffrn_reflns_theta_max         27.996
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.955
_diffrn_measured_fraction_theta_max 0.947
_diffrn_reflns_Laue_measured_fraction_full 0.955
_diffrn_reflns_Laue_measured_fraction_max 0.947
_diffrn_reflns_point_group_measured_fraction_full 0.955
_diffrn_reflns_point_group_measured_fraction_max 0.947
_reflns_Friedel_coverage         0
_reflns_number_total             4461
_reflns_number_gt                2908
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       
;
X-Area WinXpose 2.0.22.0 (STOE, 2016)
;
_computing_cell_refinement       
;
X-Area Recipe 1.33.0.0 (STOE, 2015)
;
_computing_data_reduction        
;
X-Area Integrate 1.72.0.0 (STOE, 2018)
X-Area X-Red32 1.63.4.0 (STOE, 2017) 
;
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   mixed

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          'Refined as a 2-component twin.,Twin'
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1062P)²+8.3311P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         4461
_refine_ls_number_parameters     219
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.1111
_refine_ls_R_factor_gt           0.0686
_refine_ls_wR_factor_ref         0.2208
_refine_ls_wR_factor_gt          0.201
_refine_ls_goodness_of_fit_ref   1.069
_refine_ls_restrained_S_all      1.069
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.852
_refine_diff_density_min         -0.615
_refine_diff_density_rms         0.116

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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'

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
C1 C 0.56712(18) 0.3099(7) 0.36163(14) 0.0211(8) Uani 1 1 d . . . . .
C2 C 0.52467(18) 0.2914(7) 0.38712(13) 0.0210(8) Uani 1 1 d . . . . .
C3 C 0.4869(2) 0.4681(7) 0.38887(14) 0.0240(9) Uani 1 1 d . . . . .
H3 H 0.488085 0.605708 0.373095 0.029 Uiso 1 1 calc R U . . .
C4 C 0.44773(18) 0.4449(7) 0.41331(14) 0.0230(9) Uani 1 1 d . . . . .
H4 H 0.422069 0.566873 0.413774 0.028 Uiso 1 1 calc R U . . .
C5 C 0.44498(18) 0.2455(7) 0.43746(13) 0.0216(9) Uani 1 1 d . . . . .
C6 C 0.48291(18) 0.0686(7) 0.43546(14) 0.0214(8) Uani 1 1 d . . . . .
H6 H 0.481821 -0.068934 0.451301 0.026 Uiso 1 1 calc R U . . .
C7 C 0.52189(18) 0.0907(7) 0.41083(14) 0.0222(8) Uani 1 1 d . . . . .
H7 H 0.547191 -0.031779 0.40995 0.027 Uiso 1 1 calc R U . . .
C8 C 0.40407(17) 0.2235(7) 0.46464(13) 0.0227(9) Uani 1 1 d . . . . .
C9 C 0.37023(19) 0.0283(8) 0.46207(15) 0.0264(9) Uani 1 1 d . . . . .
H9 H 0.372708 -0.091865 0.441896 0.032 Uiso 1 1 calc R U . . .
C10 C 0.3330(2) 0.0076(9) 0.48861(16) 0.0321(11) Uani 1 1 d . . . . .
H10 H 0.309866 -0.125316 0.486308 0.038 Uiso 1 1 calc R U . . .
C11 C 0.3298(2) 0.1803(9) 0.51821(15) 0.0314(11) Uani 1 1 d . . . . .
H11 H 0.304961 0.164571 0.536834 0.038 Uiso 1 1 calc R U . . .
C12 C 0.3624(2) 0.3776(8) 0.52123(14) 0.0286(10) Uani 1 1 d . . . . .
H12 H 0.359337 0.497766 0.541174 0.034 Uiso 1 1 calc R U . . .
C13 C 0.39949(19) 0.3963(7) 0.49472(14) 0.0248(9) Uani 1 1 d . . . . .
H13 H 0.422337 0.529963 0.497073 0.03 Uiso 1 1 calc R U . . .
C14 C 0.7215(2) 0.5602(7) 0.34628(16) 0.0290(10) Uani 1 1 d . . . . .
C15 C 0.7424(2) 0.4385(9) 0.39484(16) 0.0374(12) Uani 1 1 d . . . . .
H15A H 0.747763 0.278242 0.389938 0.056 Uiso 1 1 calc R U . . .
H15B H 0.711765 0.45699 0.409479 0.056 Uiso 1 1 calc R U . . .
H15C H 0.780968 0.502492 0.416178 0.056 Uiso 1 1 calc R U . . .
C16 C 0.7693(2) 0.5200(13) 0.3239(2) 0.0600(19) Uani 1 1 d . . . . .
H16A H 0.757568 0.599714 0.293069 0.09 Uiso 1 1 calc R U . . .
H16B H 0.772227 0.358578 0.318494 0.09 Uiso 1 1 calc R U . . .
H16C H 0.808655 0.575811 0.345686 0.09 Uiso 1 1 calc R U . . .
C17 C 0.7168(3) 0.8096(8) 0.3558(2) 0.0540(17) Uani 1 1 d . . . . .
H17A H 0.754544 0.860241 0.380888 0.081 Uiso 1 1 calc R U . . .
H17B H 0.682831 0.834525 0.366555 0.081 Uiso 1 1 calc R U . . .
H17C H 0.710014 0.894686 0.326179 0.081 Uiso 1 1 calc R U . . .
C18 C 0.6148(2) 0.5357(7) 0.24643(14) 0.0260(9) Uani 1 1 d . . . . .
C19 C 0.6486(3) 0.4428(9) 0.21536(18) 0.0424(13) Uani 1 1 d . . . . .
H19A H 0.627114 0.486871 0.181748 0.064 Uiso 1 1 calc R U . . .
H19B H 0.650297 0.278481 0.21775 0.064 Uiso 1 1 calc R U . . .
H19C H 0.689847 0.503703 0.226707 0.064 Uiso 1 1 calc R U . . .
C20 C 0.6118(3) 0.7923(8) 0.24295(17) 0.0419(13) Uani 1 1 d . . . . .
H20A H 0.588277 0.836763 0.209702 0.063 Uiso 1 1 calc R U . . .
H20B H 0.652908 0.853532 0.252621 0.063 Uiso 1 1 calc R U . . .
H20C H 0.592134 0.850953 0.264303 0.063 Uiso 1 1 calc R U . . .
C21 C 0.5499(2) 0.4392(8) 0.22572(16) 0.0334(11) Uani 1 1 d . . . . .
H21A H 0.525725 0.50342 0.243085 0.05 Uiso 1 1 calc R U . . .
H21B H 0.551508 0.275391 0.229423 0.05 Uiso 1 1 calc R U . . .
H21C H 0.531343 0.477609 0.19149 0.05 Uiso 1 1 calc R U . . .
P1 P 0.58650(6) 0.54937(19) 0.34107(4) 0.0260(3) Uani 1 1 d . . . . .
P2 P 0.64913(5) 0.40932(17) 0.30870(4) 0.0192(3) Uani 1 1 d . . . . .
H1 H 0.586(3) 0.176(10) 0.3603(19) 0.048(16) Uiso 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   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
C1 C2 1.470(6) . ?
C1 P1 1.680(4) . ?
C1 H1 0.92(6) . ?
C2 C3 1.394(6) . ?
C2 C7 1.401(6) . ?
C3 C4 1.380(6) . ?
C3 H3 0.95 . ?
C4 C5 1.402(6) . ?
C4 H4 0.95 . ?
C5 C6 1.399(6) . ?
C5 C8 1.479(6) . ?
C6 C7 1.381(6) . ?
C6 H6 0.95 . ?
C7 H7 0.95 . ?
C8 C13 1.395(6) . ?
C8 C9 1.397(6) . ?
C9 C10 1.389(6) . ?
C9 H9 0.95 . ?
C10 C11 1.375(7) . ?
C10 H10 0.95 . ?
C11 C12 1.390(7) . ?
C11 H11 0.95 . ?
C12 C13 1.384(6) . ?
C12 H12 0.95 . ?
C13 H13 0.95 . ?
C14 C17 1.523(7) . ?
C14 C16 1.529(7) . ?
C14 C15 1.531(6) . ?
C14 P2 1.897(4) . ?
C15 H15A 0.98 . ?
C15 H15B 0.98 . ?
C15 H15C 0.98 . ?
C16 H16A 0.98 . ?
C16 H16B 0.98 . ?
C16 H16C 0.98 . ?
C17 H17A 0.98 . ?
C17 H17B 0.98 . ?
C17 H17C 0.98 . ?
C18 C20 1.530(6) . ?
C18 C19 1.531(6) . ?
C18 C21 1.543(6) . ?
C18 P2 1.891(4) . ?
C19 H19A 0.98 . ?
C19 H19B 0.98 . ?
C19 H19C 0.98 . ?
C20 H20A 0.98 . ?
C20 H20B 0.98 . ?
C20 H20C 0.98 . ?
C21 H21A 0.98 . ?
C21 H21B 0.98 . ?
C21 H21C 0.98 . ?
P1 P2 2.2079(16) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 P1 125.6(3) . . ?
C2 C1 H1 113(3) . . ?
P1 C1 H1 121(3) . . ?
C3 C2 C7 118.3(4) . . ?
C3 C2 C1 122.2(4) . . ?
C7 C2 C1 119.5(4) . . ?
C4 C3 C2 120.6(4) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 C5 121.5(4) . . ?
C3 C4 H4 119.2 . . ?
C5 C4 H4 119.2 . . ?
C6 C5 C4 117.6(4) . . ?
C6 C5 C8 121.1(4) . . ?
C4 C5 C8 121.3(4) . . ?
C7 C6 C5 121.1(4) . . ?
C7 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
C6 C7 C2 120.9(4) . . ?
C6 C7 H7 119.5 . . ?
C2 C7 H7 119.5 . . ?
C13 C8 C9 118.0(4) . . ?
C13 C8 C5 120.5(4) . . ?
C9 C8 C5 121.4(4) . . ?
C10 C9 C8 120.9(4) . . ?
C10 C9 H9 119.6 . . ?
C8 C9 H9 119.6 . . ?
C11 C10 C9 119.7(4) . . ?
C11 C10 H10 120.2 . . ?
C9 C10 H10 120.2 . . ?
C10 C11 C12 120.8(4) . . ?
C10 C11 H11 119.6 . . ?
C12 C11 H11 119.6 . . ?
C13 C12 C11 119.0(4) . . ?
C13 C12 H12 120.5 . . ?
C11 C12 H12 120.5 . . ?
C12 C13 C8 121.5(4) . . ?
C12 C13 H13 119.2 . . ?
C8 C13 H13 119.2 . . ?
C17 C14 C16 110.5(5) . . ?
C17 C14 C15 107.7(4) . . ?
C16 C14 C15 107.8(4) . . ?
C17 C14 P2 117.4(3) . . ?
C16 C14 P2 108.7(3) . . ?
C15 C14 P2 104.2(3) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C14 C17 H17A 109.5 . . ?
C14 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C14 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C20 C18 C19 110.0(4) . . ?
C20 C18 C21 109.2(4) . . ?
C19 C18 C21 106.7(4) . . ?
C20 C18 P2 117.1(3) . . ?
C19 C18 P2 108.7(3) . . ?
C21 C18 P2 104.7(3) . . ?
C18 C19 H19A 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C18 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C18 C20 H20A 109.5 . . ?
C18 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C18 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
C18 C21 H21A 109.5 . . ?
C18 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C18 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C1 P1 P2 99.02(16) . . ?
C18 P2 C14 111.3(2) . . ?
C18 P2 P1 99.43(15) . . ?
C14 P2 P1 99.77(15) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
P1 C1 C2 C3 12.6(5) . . . . ?
P1 C1 C2 C7 -167.0(3) . . . . ?
C7 C2 C3 C4 -0.1(6) . . . . ?
C1 C2 C3 C4 -179.8(4) . . . . ?
C2 C3 C4 C5 0.6(6) . . . . ?
C3 C4 C5 C6 -0.8(6) . . . . ?
C3 C4 C5 C8 178.4(4) . . . . ?
C4 C5 C6 C7 0.4(6) . . . . ?
C8 C5 C6 C7 -178.8(4) . . . . ?
C5 C6 C7 C2 0.1(6) . . . . ?
C3 C2 C7 C6 -0.2(6) . . . . ?
C1 C2 C7 C6 179.4(4) . . . . ?
C6 C5 C8 C13 135.0(4) . . . . ?
C4 C5 C8 C13 -44.2(5) . . . . ?
C6 C5 C8 C9 -43.3(5) . . . . ?
C4 C5 C8 C9 137.5(4) . . . . ?
C13 C8 C9 C10 0.2(6) . . . . ?
C5 C8 C9 C10 178.5(4) . . . . ?
C8 C9 C10 C11 -0.7(6) . . . . ?
C9 C10 C11 C12 1.3(7) . . . . ?
C10 C11 C12 C13 -1.4(7) . . . . ?
C11 C12 C13 C8 1.0(6) . . . . ?
C9 C8 C13 C12 -0.3(6) . . . . ?
C5 C8 C13 C12 -178.7(4) . . . . ?
C2 C1 P1 P2 -179.4(3) . . . . ?
C20 C18 P2 C14 -44.9(5) . . . . ?
C19 C18 P2 C14 80.4(4) . . . . ?
C21 C18 P2 C14 -165.9(3) . . . . ?
C20 C18 P2 P1 59.6(4) . . . . ?
C19 C18 P2 P1 -175.1(3) . . . . ?
C21 C18 P2 P1 -61.4(3) . . . . ?
C17 C14 P2 C18 60.7(5) . . . . ?
C16 C14 P2 C18 -65.7(4) . . . . ?
C15 C14 P2 C18 179.6(3) . . . . ?
C17 C14 P2 P1 -43.6(4) . . . . ?
C16 C14 P2 P1 -169.9(3) . . . . ?
C15 C14 P2 P1 75.4(3) . . . . ?


# start Validation Reply Form
_vrf_PLAT029_4e                  
;
PROBLEM: diffrn_measured_fraction_theta_full value Low .      0.955 Why?
RESPONSE: The crystals were few times measured and every time 
the twinning problem was observed. Therefore for one data set 
the problem was resolved with the ROTAX program integrated with 
the WinGX. In this proces the 184 reflections were omitted.
;
_vrf_PUBL009_GLOBAL              
;
PROBLEM: _publ_author_name is missing. List of author(s) name(s).
RESPONSE: ...
;
_vrf_PUBL010_GLOBAL              
;
PROBLEM: _publ_author_address is missing. Author(s) address(es).
RESPONSE: ...
;
_vrf_PUBL012_GLOBAL              
;
PROBLEM: _publ_section_abstract is missing.
RESPONSE: ...
;
# end Validation Reply Form 
# END of CIF
####################################################################### 
# 
# 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_3d
_database_code_depnum_ccdc_archive 'CCDC 2077816'
loop_
_audit_author_name
_audit_author_address
'Lukasz Ponikiewski'
;Gdansk University of Technology
Poland
;
_audit_update_record             
;
2021-04-23 deposited with the CCDC.	2021-06-21 downloaded from the CCDC.
;

_audit_creation_date             2021-01-20T14:27:44-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         '2(C23 H26 N2 P2), C7 H8'
_chemical_formula_sum            'C53 H60 N4 P4'
_chemical_formula_weight         876.93

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   16.0860(3)
_cell_length_b                   16.7747(3)
_cell_length_c                   18.1220(4)
_cell_angle_alpha                90
_cell_angle_beta                 93.719(2)
_cell_angle_gamma                90
_cell_volume                     4879.70(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    40470
_cell_measurement_theta_min      2.63
_cell_measurement_theta_max      67.89
_cell_measurement_wavelength     1.54186

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_exptl_crystal_density_diffrn    1.194
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1864

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    1.723
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   
;
STOE X-Red32, absorption correction by Gaussian integration, analogous to
P. Coppens, "The Evaluation of Absorption and Extinction in Single-Crystal
Structure Analysis", published in
F. R. Ahmed (Editor), "Crystallographic Computing",
Munksgaard, Copenhagen (1970), 255 - 270
;
_exptl_absorpt_correction_T_min  0.6445
_exptl_absorpt_correction_T_max  0.8613
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
2 -3 -1 0.0420
-1 2 1 0.0640
2 1 1 0.1760
-2 -1 -1 0.2920
1 2 -4 0.0540
-1 -2 4 0.0550

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     1.54186
_diffrn_radiation_type           CuK\a
_diffrn_radiation_probe          x-ray
_diffrn_measurement_device       '2-circle diffractometer'
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_type            'STOE Imaging Plate'
_diffrn_detector_area_resol_mean 6.67
_diffrn_source                   'GeniX Cu, 0.05 x 0.05 mm2 microfocus'
_diffrn_source_type              ?
_diffrn_source_target            ?
_diffrn_source_voltage           50
_diffrn_source_current           0.600
_diffrn_source_power             0.030
_diffrn_radiation_monochromator  'parabolic x-ray mirror'
_diffrn_radiation_polarisn_norm  270
_diffrn_radiation_collimation    '0.6 mm diameter'
_diffrn_measurement_method       'rotation method, ω scans'
_diffrn_measurement_details      
; 657 frames, detector distance = 45 mm
;
_diffrn_reflns_av_R_equivalents  0.0191
_diffrn_reflns_av_unetI/netI     0.0169
_diffrn_reflns_number            28363
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_theta_min         2.753
_diffrn_reflns_theta_max         66.997
_diffrn_reflns_theta_full        66.997
_diffrn_measured_fraction_theta_full 0.979
_diffrn_measured_fraction_theta_max 0.979
_diffrn_reflns_Laue_measured_fraction_full 0.979
_diffrn_reflns_Laue_measured_fraction_max 0.979
_diffrn_reflns_point_group_measured_fraction_full 0.979
_diffrn_reflns_point_group_measured_fraction_max 0.979
_reflns_Friedel_coverage         0
_reflns_number_total             8513
_reflns_number_gt                7438
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       
;
X-Area WinXpose 2.0.22.0 (STOE, 2016)
;
_computing_cell_refinement       
;
X-Area Recipe 1.33.0.0 (STOE, 2015)
;
_computing_data_reduction        
;
X-Area Integrate 1.72.0.0 (STOE, 2018)
X-Area X-Red32 1.63.4.0 (STOE, 2017) 
;
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0372P)²+5.9467P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         8513
_refine_ls_number_parameters     602
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.05
_refine_ls_R_factor_gt           0.043
_refine_ls_wR_factor_ref         0.1089
_refine_ls_wR_factor_gt          0.1049
_refine_ls_goodness_of_fit_ref   1.048
_refine_ls_restrained_S_all      1.048
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.365
_refine_diff_density_min         -0.302
_refine_diff_density_rms         0.052

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
C1 C 0.44743(12) 0.46131(12) 0.78185(11) 0.0204(4) Uani 1 1 d . . . . .
C2 C 0.43170(13) 0.53672(12) 0.73986(10) 0.0201(4) Uani 1 1 d . . . . .
C3 C 0.49654(13) 0.58748(12) 0.72292(11) 0.0240(4) Uani 1 1 d . . . . .
H3 H 0.552368 0.573898 0.738157 0.029 Uiso 1 1 calc R U . . .
C4 C 0.48019(14) 0.65751(12) 0.68408(11) 0.0251(5) Uani 1 1 d . . . . .
H4 H 0.524567 0.692126 0.673374 0.03 Uiso 1 1 calc R U . . .
C5 C 0.39850(14) 0.67698(12) 0.66078(11) 0.0242(4) Uani 1 1 d . . . . .
C6 C 0.33283(14) 0.62705(13) 0.67767(11) 0.0266(5) Uani 1 1 d . . . . .
H6 H 0.277086 0.640266 0.661802 0.032 Uiso 1 1 calc R U . . .
C7 C 0.34997(13) 0.55801(12) 0.71786(11) 0.0241(4) Uani 1 1 d . . . . .
H7 H 0.305373 0.524675 0.730635 0.029 Uiso 1 1 calc R U . . .
C8 C 0.38030(15) 0.74900(13) 0.61907(12) 0.0300(5) Uani 1 1 d . . . . .
C9 C 0.42317(12) 0.46200(12) 0.85993(11) 0.0204(4) Uani 1 1 d . . . . .
C10 C 0.41516(14) 0.53423(12) 0.89700(11) 0.0251(5) Uani 1 1 d . . . . .
H10 H 0.424181 0.582663 0.871553 0.03 Uiso 1 1 calc R U . . .
C11 C 0.39431(14) 0.53714(13) 0.97025(11) 0.0262(5) Uani 1 1 d . . . . .
H11 H 0.389113 0.586949 0.994465 0.031 Uiso 1 1 calc R U . . .
C12 C 0.38123(13) 0.46663(13) 1.00747(11) 0.0248(4) Uani 1 1 d . . . . .
C13 C 0.38859(17) 0.39378(14) 0.97140(13) 0.0367(6) Uani 1 1 d . . . . .
H13 H 0.379181 0.345451 0.996882 0.044 Uiso 1 1 calc R U . . .
C14 C 0.40954(16) 0.39173(13) 0.89867(12) 0.0330(5) Uani 1 1 d . . . . .
H14 H 0.414753 0.341794 0.87468 0.04 Uiso 1 1 calc R U . . .
C15 C 0.35902(14) 0.46818(14) 1.08382(12) 0.0287(5) Uani 1 1 d . . . . .
C16 C 0.42624(15) 0.35360(17) 0.57936(13) 0.0381(6) Uani 1 1 d . . . . .
C17 C 0.35313(18) 0.4131(2) 0.58020(16) 0.0605(9) Uani 1 1 d . . . . .
H17A H 0.305613 0.392469 0.549364 0.091 Uiso 1 1 calc R U . . .
H17B H 0.370326 0.464572 0.560717 0.091 Uiso 1 1 calc R U . . .
H17C H 0.337014 0.419916 0.631043 0.091 Uiso 1 1 calc R U . . .
C18 C 0.39796(17) 0.27402(18) 0.61124(15) 0.0486(7) Uani 1 1 d . . . . .
H18A H 0.386685 0.281203 0.663318 0.073 Uiso 1 1 calc R U . . .
H18B H 0.441974 0.234134 0.607327 0.073 Uiso 1 1 calc R U . . .
H18C H 0.347174 0.255919 0.583417 0.073 Uiso 1 1 calc R U . . .
C19 C 0.44899(17) 0.34185(18) 0.49881(13) 0.0449(7) Uani 1 1 d . . . . .
H19A H 0.399566 0.324458 0.468612 0.067 Uiso 1 1 calc R U . . .
H19B H 0.492682 0.301301 0.497122 0.067 Uiso 1 1 calc R U . . .
H19C H 0.469202 0.392329 0.479461 0.067 Uiso 1 1 calc R U . . .
C20 C 0.61422(14) 0.34494(13) 0.62793(12) 0.0265(5) Uani 1 1 d . . . . .
C21 C 0.65511(16) 0.36931(15) 0.55658(13) 0.0357(5) Uani 1 1 d . . . . .
H21A H 0.707815 0.340561 0.553584 0.053 Uiso 1 1 calc R U . . .
H21B H 0.665819 0.426829 0.557329 0.053 Uiso 1 1 calc R U . . .
H21C H 0.617654 0.356028 0.51353 0.053 Uiso 1 1 calc R U . . .
C22 C 0.60485(15) 0.25427(13) 0.63050(13) 0.0318(5) Uani 1 1 d . . . . .
H22A H 0.660099 0.22943 0.632915 0.048 Uiso 1 1 calc R U . . .
H22B H 0.572652 0.236029 0.585912 0.048 Uiso 1 1 calc R U . . .
H22C H 0.575789 0.239254 0.674307 0.048 Uiso 1 1 calc R U . . .
C23 C 0.67290(15) 0.37150(15) 0.69344(13) 0.0365(6) Uani 1 1 d . . . . .
H23A H 0.651106 0.352954 0.739691 0.055 Uiso 1 1 calc R U . . .
H23B H 0.676734 0.429805 0.694022 0.055 Uiso 1 1 calc R U . . .
H23C H 0.728349 0.348708 0.688446 0.055 Uiso 1 1 calc R U . . .
C24 C 0.94252(12) 0.53357(12) 0.71659(11) 0.0214(4) Uani 1 1 d . . . . .
C25 C 0.92466(13) 0.52924(12) 0.63515(11) 0.0211(4) Uani 1 1 d . . . . .
C26 C 0.95558(14) 0.58731(13) 0.58834(11) 0.0261(5) Uani 1 1 d . . . . .
H26 H 0.990647 0.628338 0.608842 0.031 Uiso 1 1 calc R U . . .
C27 C 0.93593(14) 0.58587(13) 0.51298(11) 0.0271(5) Uani 1 1 d . . . . .
H27 H 0.957037 0.625924 0.482188 0.033 Uiso 1 1 calc R U . . .
C28 C 0.88518(13) 0.52567(13) 0.48222(11) 0.0247(4) Uani 1 1 d . . . . .
C29 C 0.85621(15) 0.46599(14) 0.52707(12) 0.0308(5) Uani 1 1 d . . . . .
H29 H 0.823029 0.42391 0.505997 0.037 Uiso 1 1 calc R U . . .
C30 C 0.87579(15) 0.46799(13) 0.60254(12) 0.0290(5) Uani 1 1 d . . . . .
H30 H 0.855691 0.426992 0.632863 0.035 Uiso 1 1 calc R U . . .
C31 C 0.86394(14) 0.52567(14) 0.40317(12) 0.0284(5) Uani 1 1 d . . . . .
C32 C 0.92414(13) 0.45996(12) 0.75935(10) 0.0207(4) Uani 1 1 d . . . . .
C33 C 0.84865(13) 0.45293(13) 0.79275(11) 0.0237(4) Uani 1 1 d . . . . .
H33 H 0.809233 0.495109 0.788277 0.028 Uiso 1 1 calc R U . . .
C34 C 0.83062(13) 0.38513(13) 0.83233(11) 0.0244(4) Uani 1 1 d . . . . .
H34 H 0.779192 0.380663 0.854982 0.029 Uiso 1 1 calc R U . . .
C35 C 0.88895(13) 0.32341(12) 0.83854(11) 0.0232(4) Uani 1 1 d . . . . .
C36 C 0.96486(14) 0.33020(13) 0.80571(12) 0.0276(5) Uani 1 1 d . . . . .
H36 H 1.004659 0.288381 0.810658 0.033 Uiso 1 1 calc R U . . .
C37 C 0.98181(14) 0.39793(13) 0.76605(12) 0.0268(5) Uani 1 1 d . . . . .
H37 H 1.033116 0.402287 0.743187 0.032 Uiso 1 1 calc R U . . .
C38 C 0.87015(14) 0.25251(13) 0.87912(12) 0.0277(5) Uani 1 1 d . . . . .
C39 C 1.11642(15) 0.62975(17) 0.88308(13) 0.0390(6) Uani 1 1 d . . . . .
C40 C 1.15394(18) 0.60108(19) 0.95849(15) 0.0504(7) Uani 1 1 d . . . . .
H40A H 1.150122 0.542857 0.961129 0.076 Uiso 1 1 calc R U . . .
H40B H 1.123137 0.62483 0.997909 0.076 Uiso 1 1 calc R U . . .
H40C H 1.212527 0.617256 0.964586 0.076 Uiso 1 1 calc R U . . .
C41 C 1.12829(18) 0.72019(18) 0.87641(16) 0.0502(7) Uani 1 1 d . . . . .
H41A H 1.187928 0.732675 0.879319 0.075 Uiso 1 1 calc R U . . .
H41B H 1.101787 0.747056 0.916777 0.075 Uiso 1 1 calc R U . . .
H41C H 1.102734 0.738591 0.828875 0.075 Uiso 1 1 calc R U . . .
C42 C 1.16317(19) 0.5894(2) 0.82228(18) 0.0665(10) Uani 1 1 d . . . . .
H42A H 1.222794 0.601152 0.829769 0.1 Uiso 1 1 calc R U . . .
H42B H 1.142075 0.609616 0.773889 0.1 Uiso 1 1 calc R U . . .
H42C H 1.154544 0.531631 0.82426 0.1 Uiso 1 1 calc R U . . .
C43 C 0.93300(14) 0.66440(15) 0.91630(12) 0.0336(5) Uani 1 1 d . . . . .
C44 C 0.92039(18) 0.74520(16) 0.87775(15) 0.0458(7) Uani 1 1 d . . . . .
H44A H 0.879594 0.776588 0.903236 0.069 Uiso 1 1 calc R U . . .
H44B H 0.899973 0.736778 0.826213 0.069 Uiso 1 1 calc R U . . .
H44C H 0.973526 0.773908 0.879156 0.069 Uiso 1 1 calc R U . . .
C45 C 0.84786(17) 0.6219(2) 0.91382(16) 0.0515(7) Uani 1 1 d . . . . .
H45A H 0.854171 0.56977 0.937966 0.077 Uiso 1 1 calc R U . . .
H45B H 0.827063 0.614568 0.862227 0.077 Uiso 1 1 calc R U . . .
H45C H 0.80823 0.654309 0.939673 0.077 Uiso 1 1 calc R U . . .
C46 C 0.96374(16) 0.67664(18) 0.99731(13) 0.0423(6) Uani 1 1 d . . . . .
H46A H 1.016561 0.705932 0.999637 0.064 Uiso 1 1 calc R U . . .
H46B H 0.972101 0.624673 1.021363 0.064 Uiso 1 1 calc R U . . .
H46C H 0.922227 0.70715 1.022756 0.064 Uiso 1 1 calc R U . . .
C47 C 0.7712(2) 0.78929(16) 0.6578(2) 0.0387(13) Uani 0.599(5) 1 d G . P A 1
C48 C 0.7752(3) 0.7318(2) 0.60290(16) 0.051(3) Uani 0.599(5) 1 d G . P A 1
H48 H 0.794718 0.745686 0.556224 0.061 Uiso 0.599(5) 1 calc R U P A 1
C49 C 0.7507(2) 0.65395(18) 0.61630(18) 0.0449(13) Uani 0.599(5) 1 d G . P A 1
H49 H 0.753401 0.614654 0.578792 0.054 Uiso 0.599(5) 1 calc R U P A 1
C50 C 0.7222(2) 0.63362(17) 0.6846(2) 0.0431(12) Uani 0.599(5) 1 d G . P A 1
H50 H 0.705387 0.580423 0.693757 0.052 Uiso 0.599(5) 1 calc R U P A 1
C51 C 0.7182(3) 0.6911(2) 0.73948(17) 0.0519(18) Uani 0.599(5) 1 d G . P A 1
H51 H 0.69869 0.677224 0.786156 0.062 Uiso 0.599(5) 1 calc R U P A 1
C52 C 0.7427(3) 0.7690(2) 0.72608(18) 0.0497(17) Uani 0.599(5) 1 d G . P A 1
H52 H 0.740006 0.808257 0.76359 0.06 Uiso 0.599(5) 1 calc R U P A 1
C53 C 0.7981(3) 0.8745(3) 0.6463(3) 0.0537(14) Uani 0.599(5) 1 d . . P A 1
H53A H 0.790527 0.90544 0.691256 0.081 Uiso 0.599(5) 1 calc R U P A 1
H53B H 0.856981 0.875588 0.635332 0.081 Uiso 0.599(5) 1 calc R U P A 1
H53C H 0.764292 0.897857 0.604839 0.081 Uiso 0.599(5) 1 calc R U P A 1
C47A C 0.7411(3) 0.6843(2) 0.6613(3) 0.0386(17) Uani 0.401(5) 1 d G . P A 2
C48A C 0.7281(4) 0.7117(3) 0.7320(2) 0.045(3) Uani 0.401(5) 1 d G . P A 2
H48A H 0.704157 0.677398 0.766579 0.054 Uiso 0.401(5) 1 calc R U P A 2
C49A C 0.7501(5) 0.7892(4) 0.7522(2) 0.058(3) Uani 0.401(5) 1 d G . P A 2
H49A H 0.741261 0.807847 0.800528 0.07 Uiso 0.401(5) 1 calc R U P A 2
C50A C 0.7851(3) 0.8393(2) 0.7016(3) 0.0449(19) Uani 0.401(5) 1 d G . P A 2
H50A H 0.800202 0.89228 0.715383 0.054 Uiso 0.401(5) 1 calc R U P A 2
C51A C 0.7981(3) 0.8120(3) 0.6309(3) 0.046(2) Uani 0.401(5) 1 d G . P A 2
H51A H 0.822039 0.846264 0.596289 0.055 Uiso 0.401(5) 1 calc R U P A 2
C52A C 0.7761(4) 0.7345(3) 0.6107(2) 0.029(4) Uani 0.401(5) 1 d G . P A 2
H52A H 0.784936 0.715814 0.562338 0.034 Uiso 0.401(5) 1 calc R U P A 2
C53A C 0.7182(5) 0.6011(5) 0.6416(5) 0.0471(19) Uani 0.401(5) 1 d . . P A 2
H53D H 0.730822 0.590624 0.590342 0.071 Uiso 0.401(5) 1 calc R U P A 2
H53E H 0.750028 0.564398 0.674633 0.071 Uiso 0.401(5) 1 calc R U P A 2
H53F H 0.658458 0.593256 0.64687 0.071 Uiso 0.401(5) 1 calc R U P A 2
N1 N 0.36452(14) 0.80549(12) 0.58542(11) 0.0409(5) Uani 1 1 d . . . B 2
N2 N 0.34125(13) 0.46858(13) 1.14401(11) 0.0376(5) Uani 1 1 d . . . C 2
N3 N 0.85520(13) 0.19629(12) 0.91205(11) 0.0368(5) Uani 1 1 d . . . D 2
N4 N 0.84633(13) 0.52720(13) 0.34119(10) 0.0380(5) Uani 1 1 d . . . E 2
P1 P 0.48889(4) 0.37689(3) 0.74791(3) 0.02589(13) Uani 1 1 d . . . F 2
P2 P 0.51581(4) 0.40693(3) 0.63244(3) 0.02658(14) Uani 1 1 d . . . F 2
P3 P 0.97787(4) 0.62014(3) 0.75471(3) 0.03089(15) Uani 1 1 d . . . G 2
P4 P 1.00499(4) 0.59022(3) 0.87307(3) 0.02769(14) Uani 1 1 d . . . G 2



#----------------------------------------------------------------------------#
#                   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
C1 C2 1.489(3) . ?
C1 C9 1.492(3) . ?
C1 P1 1.697(2) . ?
C2 C7 1.395(3) . ?
C2 C3 1.396(3) . ?
C3 C4 1.386(3) . ?
C3 H3 0.95 . ?
C4 C5 1.393(3) . ?
C4 H4 0.95 . ?
C5 C6 1.398(3) . ?
C5 C8 1.445(3) . ?
C6 C7 1.386(3) . ?
C6 H6 0.95 . ?
C7 H7 0.95 . ?
C8 N1 1.146(3) . ?
C9 C10 1.395(3) . ?
C9 C14 1.397(3) . ?
C10 C11 1.391(3) . ?
C10 H10 0.95 . ?
C11 C12 1.384(3) . ?
C11 H11 0.95 . ?
C12 C13 1.395(3) . ?
C12 C15 1.451(3) . ?
C13 C14 1.382(3) . ?
C13 H13 0.95 . ?
C14 H14 0.95 . ?
C15 N2 1.146(3) . ?
C16 C18 1.535(4) . ?
C16 C19 1.540(3) . ?
C16 C17 1.543(4) . ?
C16 P2 1.903(3) . ?
C17 H17A 0.98 . ?
C17 H17B 0.98 . ?
C17 H17C 0.98 . ?
C18 H18A 0.98 . ?
C18 H18B 0.98 . ?
C18 H18C 0.98 . ?
C19 H19A 0.98 . ?
C19 H19B 0.98 . ?
C19 H19C 0.98 . ?
C20 C22 1.529(3) . ?
C20 C23 1.534(3) . ?
C20 C21 1.543(3) . ?
C20 P2 1.900(2) . ?
C21 H21A 0.98 . ?
C21 H21B 0.98 . ?
C21 H21C 0.98 . ?
C22 H22A 0.98 . ?
C22 H22B 0.98 . ?
C22 H22C 0.98 . ?
C23 H23A 0.98 . ?
C23 H23B 0.98 . ?
C23 H23C 0.98 . ?
C24 C25 1.487(3) . ?
C24 C32 1.497(3) . ?
C24 P3 1.691(2) . ?
C25 C30 1.401(3) . ?
C25 C26 1.404(3) . ?
C26 C27 1.382(3) . ?
C26 H26 0.95 . ?
C27 C28 1.392(3) . ?
C27 H27 0.95 . ?
C28 C29 1.389(3) . ?
C28 C31 1.451(3) . ?
C29 C30 1.384(3) . ?
C29 H29 0.95 . ?
C30 H30 0.95 . ?
C31 N4 1.141(3) . ?
C32 C37 1.394(3) . ?
C32 C33 1.396(3) . ?
C33 C34 1.385(3) . ?
C33 H33 0.95 . ?
C34 C35 1.397(3) . ?
C34 H34 0.95 . ?
C35 C36 1.397(3) . ?
C35 C38 1.441(3) . ?
C36 C37 1.381(3) . ?
C36 H36 0.95 . ?
C37 H37 0.95 . ?
C38 N3 1.150(3) . ?
C39 C42 1.531(3) . ?
C39 C41 1.535(4) . ?
C39 C40 1.535(4) . ?
C39 P4 1.909(3) . ?
C40 H40A 0.98 . ?
C40 H40B 0.98 . ?
C40 H40C 0.98 . ?
C41 H41A 0.98 . ?
C41 H41B 0.98 . ?
C41 H41C 0.98 . ?
C42 H42A 0.98 . ?
C42 H42B 0.98 . ?
C42 H42C 0.98 . ?
C43 C44 1.532(4) . ?
C43 C46 1.532(3) . ?
C43 C45 1.542(3) . ?
C43 P4 1.903(2) . ?
C44 H44A 0.98 . ?
C44 H44B 0.98 . ?
C44 H44C 0.98 . ?
C45 H45A 0.98 . ?
C45 H45B 0.98 . ?
C45 H45C 0.98 . ?
C46 H46A 0.98 . ?
C46 H46B 0.98 . ?
C46 H46C 0.98 . ?
C47 C48 1.39 . ?
C47 C52 1.39 . ?
C47 C53 1.512(6) . ?
C48 C49 1.39 . ?
C48 H48 0.95 . ?
C49 C50 1.39 . ?
C49 H49 0.95 . ?
C50 C51 1.39 . ?
C50 H50 0.95 . ?
C51 C52 1.39 . ?
C51 H51 0.95 . ?
C52 H52 0.95 . ?
C53 H53A 0.98 . ?
C53 H53B 0.98 . ?
C53 H53C 0.98 . ?
C47A C48A 1.39 . ?
C47A C52A 1.39 . ?
C47A C53A 1.481(9) . ?
C48A C49A 1.39 . ?
C48A H48A 0.95 . ?
C49A C50A 1.39 . ?
C49A H49A 0.95 . ?
C50A C51A 1.39 . ?
C50A H50A 0.95 . ?
C51A C52A 1.39 . ?
C51A H51A 0.95 . ?
C52A H52A 0.95 . ?
C53A H53D 0.98 . ?
C53A H53E 0.98 . ?
C53A H53F 0.98 . ?
P1 P2 2.2222(8) . ?
P3 P4 2.2184(8) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C9 115.58(17) . . ?
C2 C1 P1 125.53(14) . . ?
C9 C1 P1 118.89(15) . . ?
C7 C2 C3 118.99(19) . . ?
C7 C2 C1 119.27(18) . . ?
C3 C2 C1 121.73(18) . . ?
C4 C3 C2 120.6(2) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C3 C4 C5 119.8(2) . . ?
C3 C4 H4 120.1 . . ?
C5 C4 H4 120.1 . . ?
C4 C5 C6 120.31(19) . . ?
C4 C5 C8 120.7(2) . . ?
C6 C5 C8 119.0(2) . . ?
C7 C6 C5 119.2(2) . . ?
C7 C6 H6 120.4 . . ?
C5 C6 H6 120.4 . . ?
C6 C7 C2 121.0(2) . . ?
C6 C7 H7 119.5 . . ?
C2 C7 H7 119.5 . . ?
N1 C8 C5 178.7(3) . . ?
C10 C9 C14 117.93(18) . . ?
C10 C9 C1 120.08(18) . . ?
C14 C9 C1 121.97(18) . . ?
C11 C10 C9 121.69(19) . . ?
C11 C10 H10 119.2 . . ?
C9 C10 H10 119.2 . . ?
C12 C11 C10 119.25(19) . . ?
C12 C11 H11 120.4 . . ?
C10 C11 H11 120.4 . . ?
C11 C12 C13 120.01(19) . . ?
C11 C12 C15 120.2(2) . . ?
C13 C12 C15 119.7(2) . . ?
C14 C13 C12 120.2(2) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C13 C14 C9 121.0(2) . . ?
C13 C14 H14 119.5 . . ?
C9 C14 H14 119.5 . . ?
N2 C15 C12 179.3(3) . . ?
C18 C16 C19 109.9(2) . . ?
C18 C16 C17 108.3(2) . . ?
C19 C16 C17 108.7(2) . . ?
C18 C16 P2 116.86(17) . . ?
C19 C16 P2 108.69(18) . . ?
C17 C16 P2 104.10(19) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C22 C20 C23 108.80(19) . . ?
C22 C20 C21 109.70(18) . . ?
C23 C20 C21 107.28(19) . . ?
C22 C20 P2 117.32(16) . . ?
C23 C20 P2 106.28(15) . . ?
C21 C20 P2 107.01(16) . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C20 C22 H22A 109.5 . . ?
C20 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C20 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C20 C23 H23A 109.5 . . ?
C20 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C20 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C25 C24 C32 116.20(17) . . ?
C25 C24 P3 119.06(15) . . ?
C32 C24 P3 124.70(14) . . ?
C30 C25 C26 117.72(18) . . ?
C30 C25 C24 121.43(18) . . ?
C26 C25 C24 120.84(18) . . ?
C27 C26 C25 121.2(2) . . ?
C27 C26 H26 119.4 . . ?
C25 C26 H26 119.4 . . ?
C26 C27 C28 119.9(2) . . ?
C26 C27 H27 120 . . ?
C28 C27 H27 120 . . ?
C29 C28 C27 119.93(19) . . ?
C29 C28 C31 120.7(2) . . ?
C27 C28 C31 119.3(2) . . ?
C30 C29 C28 119.8(2) . . ?
C30 C29 H29 120.1 . . ?
C28 C29 H29 120.1 . . ?
C29 C30 C25 121.3(2) . . ?
C29 C30 H30 119.3 . . ?
C25 C30 H30 119.3 . . ?
N4 C31 C28 178.5(3) . . ?
C37 C32 C33 119.46(19) . . ?
C37 C32 C24 120.53(18) . . ?
C33 C32 C24 120.02(18) . . ?
C34 C33 C32 120.7(2) . . ?
C34 C33 H33 119.6 . . ?
C32 C33 H33 119.6 . . ?
C33 C34 C35 119.2(2) . . ?
C33 C34 H34 120.4 . . ?
C35 C34 H34 120.4 . . ?
C34 C35 C36 120.42(19) . . ?
C34 C35 C38 119.39(19) . . ?
C36 C35 C38 120.2(2) . . ?
C37 C36 C35 119.7(2) . . ?
C37 C36 H36 120.1 . . ?
C35 C36 H36 120.1 . . ?
C36 C37 C32 120.4(2) . . ?
C36 C37 H37 119.8 . . ?
C32 C37 H37 119.8 . . ?
N3 C38 C35 179.4(2) . . ?
C42 C39 C41 108.1(2) . . ?
C42 C39 C40 108.6(2) . . ?
C41 C39 C40 109.6(2) . . ?
C42 C39 P4 106.26(18) . . ?
C41 C39 P4 117.18(19) . . ?
C40 C39 P4 106.77(19) . . ?
C39 C40 H40A 109.5 . . ?
C39 C40 H40B 109.5 . . ?
H40A C40 H40B 109.5 . . ?
C39 C40 H40C 109.5 . . ?
H40A C40 H40C 109.5 . . ?
H40B C40 H40C 109.5 . . ?
C39 C41 H41A 109.5 . . ?
C39 C41 H41B 109.5 . . ?
H41A C41 H41B 109.5 . . ?
C39 C41 H41C 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 109.5 . . ?
C39 C42 H42A 109.5 . . ?
C39 C42 H42B 109.5 . . ?
H42A C42 H42B 109.5 . . ?
C39 C42 H42C 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 109.5 . . ?
C44 C43 C46 110.1(2) . . ?
C44 C43 C45 107.7(2) . . ?
C46 C43 C45 108.7(2) . . ?
C44 C43 P4 117.18(17) . . ?
C46 C43 P4 108.36(17) . . ?
C45 C43 P4 104.39(17) . . ?
C43 C44 H44A 109.5 . . ?
C43 C44 H44B 109.5 . . ?
H44A C44 H44B 109.5 . . ?
C43 C44 H44C 109.5 . . ?
H44A C44 H44C 109.5 . . ?
H44B C44 H44C 109.5 . . ?
C43 C45 H45A 109.5 . . ?
C43 C45 H45B 109.5 . . ?
H45A C45 H45B 109.5 . . ?
C43 C45 H45C 109.5 . . ?
H45A C45 H45C 109.5 . . ?
H45B C45 H45C 109.5 . . ?
C43 C46 H46A 109.5 . . ?
C43 C46 H46B 109.5 . . ?
H46A C46 H46B 109.5 . . ?
C43 C46 H46C 109.5 . . ?
H46A C46 H46C 109.5 . . ?
H46B C46 H46C 109.5 . . ?
C48 C47 C52 120 . . ?
C48 C47 C53 122.1(3) . . ?
C52 C47 C53 117.9(3) . . ?
C49 C48 C47 120 . . ?
C49 C48 H48 120 . . ?
C47 C48 H48 120 . . ?
C48 C49 C50 120 . . ?
C48 C49 H49 120 . . ?
C50 C49 H49 120 . . ?
C51 C50 C49 120 . . ?
C51 C50 H50 120 . . ?
C49 C50 H50 120 . . ?
C50 C51 C52 120 . . ?
C50 C51 H51 120 . . ?
C52 C51 H51 120 . . ?
C51 C52 C47 120 . . ?
C51 C52 H52 120 . . ?
C47 C52 H52 120 . . ?
C47 C53 H53A 109.5 . . ?
C47 C53 H53B 109.5 . . ?
H53A C53 H53B 109.5 . . ?
C47 C53 H53C 109.5 . . ?
H53A C53 H53C 109.5 . . ?
H53B C53 H53C 109.5 . . ?
C48A C47A C52A 120 . . ?
C48A C47A C53A 118.9(5) . . ?
C52A C47A C53A 121.1(5) . . ?
C47A C48A C49A 120 . . ?
C47A C48A H48A 120 . . ?
C49A C48A H48A 120 . . ?
C50A C49A C48A 120 . . ?
C50A C49A H49A 120 . . ?
C48A C49A H49A 120 . . ?
C49A C50A C51A 120 . . ?
C49A C50A H50A 120 . . ?
C51A C50A H50A 120 . . ?
C50A C51A C52A 120 . . ?
C50A C51A H51A 120 . . ?
C52A C51A H51A 120 . . ?
C51A C52A C47A 120 . . ?
C51A C52A H52A 120 . . ?
C47A C52A H52A 120 . . ?
C47A C53A H53D 109.5 . . ?
C47A C53A H53E 109.5 . . ?
H53D C53A H53E 109.5 . . ?
C47A C53A H53F 109.5 . . ?
H53D C53A H53F 109.5 . . ?
H53E C53A H53F 109.5 . . ?
C1 P1 P2 104.90(7) . . ?
C20 P2 C16 109.06(10) . . ?
C20 P2 P1 97.48(7) . . ?
C16 P2 P1 100.48(8) . . ?
C24 P3 P4 103.92(7) . . ?
C43 P4 C39 109.05(11) . . ?
C43 P4 P3 99.40(8) . . ?
C39 P4 P3 97.93(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
C9 C1 C2 C7 -72.1(2) . . . . ?
P1 C1 C2 C7 107.3(2) . . . . ?
C9 C1 C2 C3 106.8(2) . . . . ?
P1 C1 C2 C3 -73.8(2) . . . . ?
C7 C2 C3 C4 -0.8(3) . . . . ?
C1 C2 C3 C4 -179.69(18) . . . . ?
C2 C3 C4 C5 -0.9(3) . . . . ?
C3 C4 C5 C6 1.3(3) . . . . ?
C3 C4 C5 C8 -178.89(19) . . . . ?
C4 C5 C6 C7 0.0(3) . . . . ?
C8 C5 C6 C7 -179.80(19) . . . . ?
C5 C6 C7 C2 -1.7(3) . . . . ?
C3 C2 C7 C6 2.1(3) . . . . ?
C1 C2 C7 C6 -178.95(18) . . . . ?
C2 C1 C9 C10 -21.6(3) . . . . ?
P1 C1 C9 C10 159.00(16) . . . . ?
C2 C1 C9 C14 159.8(2) . . . . ?
P1 C1 C9 C14 -19.6(3) . . . . ?
C14 C9 C10 C11 0.0(3) . . . . ?
C1 C9 C10 C11 -178.68(19) . . . . ?
C9 C10 C11 C12 0.1(3) . . . . ?
C10 C11 C12 C13 -0.3(3) . . . . ?
C10 C11 C12 C15 -179.7(2) . . . . ?
C11 C12 C13 C14 0.5(4) . . . . ?
C15 C12 C13 C14 179.9(2) . . . . ?
C12 C13 C14 C9 -0.4(4) . . . . ?
C10 C9 C14 C13 0.1(3) . . . . ?
C1 C9 C14 C13 178.8(2) . . . . ?
C32 C24 C25 C30 14.6(3) . . . . ?
P3 C24 C25 C30 -163.11(17) . . . . ?
C32 C24 C25 C26 -166.21(19) . . . . ?
P3 C24 C25 C26 16.1(3) . . . . ?
C30 C25 C26 C27 2.4(3) . . . . ?
C24 C25 C26 C27 -176.8(2) . . . . ?
C25 C26 C27 C28 -0.5(3) . . . . ?
C26 C27 C28 C29 -1.7(3) . . . . ?
C26 C27 C28 C31 179.0(2) . . . . ?
C27 C28 C29 C30 2.0(3) . . . . ?
C31 C28 C29 C30 -178.7(2) . . . . ?
C28 C29 C30 C25 -0.1(4) . . . . ?
C26 C25 C30 C29 -2.1(3) . . . . ?
C24 C25 C30 C29 177.1(2) . . . . ?
C25 C24 C32 C37 83.3(2) . . . . ?
P3 C24 C32 C37 -99.1(2) . . . . ?
C25 C24 C32 C33 -96.5(2) . . . . ?
P3 C24 C32 C33 81.1(2) . . . . ?
C37 C32 C33 C34 0.0(3) . . . . ?
C24 C32 C33 C34 179.83(18) . . . . ?
C32 C33 C34 C35 -0.1(3) . . . . ?
C33 C34 C35 C36 0.5(3) . . . . ?
C33 C34 C35 C38 -179.48(19) . . . . ?
C34 C35 C36 C37 -0.9(3) . . . . ?
C38 C35 C36 C37 179.10(19) . . . . ?
C35 C36 C37 C32 0.8(3) . . . . ?
C33 C32 C37 C36 -0.4(3) . . . . ?
C24 C32 C37 C36 179.79(19) . . . . ?
C52 C47 C48 C49 0 . . . . ?
C53 C47 C48 C49 179.3(4) . . . . ?
C47 C48 C49 C50 0 . . . . ?
C48 C49 C50 C51 0 . . . . ?
C49 C50 C51 C52 0 . . . . ?
C50 C51 C52 C47 0 . . . . ?
C48 C47 C52 C51 0 . . . . ?
C53 C47 C52 C51 -179.3(4) . . . . ?
C52A C47A C48A C49A 0 . . . . ?
C53A C47A C48A C49A 179.1(5) . . . . ?
C47A C48A C49A C50A 0 . . . . ?
C48A C49A C50A C51A 0 . . . . ?
C49A C50A C51A C52A 0 . . . . ?
C50A C51A C52A C47A 0 . . . . ?
C48A C47A C52A C51A 0 . . . . ?
C53A C47A C52A C51A -179.1(5) . . . . ?
C2 C1 P1 P2 1.57(19) . . . . ?
C9 C1 P1 P2 -179.05(14) . . . . ?
C25 C24 P3 P4 -174.81(14) . . . . ?
C32 C24 P3 P4 7.69(19) . . . . ?



# END of CIF
####################################################################### 
# 
# 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_4d
_database_code_depnum_ccdc_archive 'CCDC 2077817'
loop_
_audit_author_name
_audit_author_address
'Lukasz Ponikiewski'
;Gdansk University of Technology
Poland
;
_audit_update_record             
;
2021-04-23 deposited with the CCDC.	2021-06-21 downloaded from the CCDC.
;

_audit_creation_date             2021-01-15T12:02:45-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         '2(C17 H29 N P2)'
_chemical_formula_sum            'C34 H58 N2 P4'
_chemical_formula_weight         618.7

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'C 2/c'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_Int_Tables_number      15
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   40.670(2)
_cell_length_b                   6.1403(2)
_cell_length_c                   35.368(2)
_cell_angle_alpha                90
_cell_angle_beta                 122.345(4)
_cell_angle_gamma                90
_cell_volume                     7462.0(7)
_cell_formula_units_Z            8
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    10815
_cell_measurement_theta_min      35.16
_cell_measurement_theta_max      90.00
_cell_measurement_wavelength     1.54186

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.11
_exptl_crystal_density_diffrn    1.101
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             2688

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    2.033
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   
;
STOE X-Red32, absorption correction by Gaussian integration, analogous to
P. Coppens, "The Evaluation of Absorption and Extinction in Single-Crystal
Structure Analysis", published in
F. R. Ahmed (Editor), "Crystallographic Computing",
Munksgaard, Copenhagen (1970), 255 - 270
;
_exptl_absorpt_correction_T_min  0.8582
_exptl_absorpt_correction_T_max  0.9832
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-2 0 1 0.0130
5 0 -3 0.0160
-2 6 -1 0.0940
-1 -4 2 0.1700
1 0 5 0.0090
0 0 -1 0.0180

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     1.54186
_diffrn_radiation_type           CuK\a
_diffrn_radiation_probe          x-ray
_diffrn_standards_number         0
_diffrn_measurement_device       '2-circle diffractometer'
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_type            'STOE Imaging Plate'
_diffrn_detector_area_resol_mean 6.67
_diffrn_source                   'GeniX Cu, 0.05 x 0.05 mm2 microfocus'
_diffrn_source_type              ?
_diffrn_source_target            ?
_diffrn_source_voltage           50
_diffrn_source_current           0.600
_diffrn_source_power             0.030
_diffrn_radiation_monochromator  'parabolic x-ray mirror'
_diffrn_radiation_polarisn_norm  270
_diffrn_radiation_collimation    '0.6 mm diameter'
_diffrn_measurement_method       'rotation method, ω scans'
_diffrn_measurement_details      
; 1132 frames, detector distance = 45 mm
;
_diffrn_reflns_av_R_equivalents  0.0935
_diffrn_reflns_av_unetI/netI     0.1237
_diffrn_reflns_number            22830
_diffrn_reflns_limit_h_min       -48
_diffrn_reflns_limit_h_max       48
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -42
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_theta_min         2.688
_diffrn_reflns_theta_max         66.493
_diffrn_reflns_theta_full        66.493
_diffrn_measured_fraction_theta_full 0.961
_diffrn_measured_fraction_theta_max 0.961
_diffrn_reflns_Laue_measured_fraction_full 0.961
_diffrn_reflns_Laue_measured_fraction_max 0.961
_diffrn_reflns_point_group_measured_fraction_full 0.961
_diffrn_reflns_point_group_measured_fraction_max 0.961
_reflns_Friedel_coverage         0
_reflns_number_total             6337
_reflns_number_gt                2999
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       
;
X-Area WinXpose 2.0.22.0 (STOE, 2016)
;
_computing_cell_refinement       
;
X-Area Recipe 1.33.0.0 (STOE, 2015)
;
_computing_data_reduction        
;
X-Area Integrate 1.72.0.0 (STOE, 2018)
X-Area X-Red32 1.63.4.0 (STOE, 2017) 
;
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   mixed

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1089P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         6337
_refine_ls_number_parameters     385
_refine_ls_number_restraints     2
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.1802
_refine_ls_R_factor_gt           0.0812
_refine_ls_wR_factor_ref         0.2331
_refine_ls_wR_factor_gt          0.1899
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_restrained_S_all      1.042
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.756
_refine_diff_density_min         -0.397
_refine_diff_density_rms         0.075

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
C1 C 0.55957(18) 0.2376(11) 0.59943(19) 0.0453(16) Uani 1 1 d D . . . .
C2 C 0.59085(15) 0.2903(11) 0.59319(18) 0.0393(15) Uani 1 1 d . . . . .
C3 C 0.62119(16) 0.1480(10) 0.60327(18) 0.0410(15) Uani 1 1 d . . . . .
H3 H 0.62227 0.010631 0.616257 0.049 Uiso 1 1 calc R U . . .
C4 C 0.64976(16) 0.2010(10) 0.59492(18) 0.0402(15) Uani 1 1 d . . . . .
H4 H 0.669905 0.099567 0.60196 0.048 Uiso 1 1 calc R U . . .
C5 C 0.64928(16) 0.4065(10) 0.57581(17) 0.0359(14) Uani 1 1 d . . . . .
C6 C 0.61978(17) 0.5494(10) 0.56727(19) 0.0460(16) Uani 1 1 d . . . . .
H6 H 0.61904 0.689479 0.555438 0.055 Uiso 1 1 calc R U . . .
C7 C 0.59148(18) 0.4927(10) 0.5756(2) 0.0472(16) Uani 1 1 d . . . . .
H7 H 0.571613 0.595173 0.569056 0.057 Uiso 1 1 calc R U . . .
C8 C 0.70569(19) 0.3053(11) 0.5718(2) 0.0565(18) Uani 1 1 d . . . . .
H8A H 0.718127 0.235191 0.601166 0.085 Uiso 1 1 calc R U . . .
H8B H 0.725496 0.378992 0.568649 0.085 Uiso 1 1 calc R U . . .
H8C H 0.692522 0.194923 0.548269 0.085 Uiso 1 1 calc R U . . .
C9 C 0.67686(19) 0.6720(11) 0.5488(2) 0.0572(19) Uani 1 1 d . . . . .
H9A H 0.652661 0.686669 0.519437 0.086 Uiso 1 1 calc R U . . .
H9B H 0.699153 0.684633 0.545339 0.086 Uiso 1 1 calc R U . . .
H9C H 0.678198 0.787201 0.568722 0.086 Uiso 1 1 calc R U . . .
C10 C 0.46181(19) -0.0748(11) 0.5538(2) 0.0566(19) Uani 1 1 d . . . . .
C11 C 0.4593(2) 0.0735(12) 0.5181(2) 0.073(2) Uani 1 1 d . . . . .
H11A H 0.44157 0.009627 0.488531 0.109 Uiso 1 1 calc R U . . .
H11B H 0.48517 0.090452 0.522861 0.109 Uiso 1 1 calc R U . . .
H11C H 0.449377 0.216283 0.519841 0.109 Uiso 1 1 calc R U . . .
C12 C 0.4214(2) -0.0903(17) 0.5463(3) 0.109(3) Uani 1 1 d . . . . .
H12A H 0.415116 0.046743 0.555294 0.163 Uiso 1 1 calc R U . . .
H12B H 0.420789 -0.209987 0.564299 0.163 Uiso 1 1 calc R U . . .
H12C H 0.402203 -0.117835 0.514584 0.163 Uiso 1 1 calc R U . . .
C13 C 0.4744(2) -0.3015(12) 0.5476(2) 0.092(3) Uani 1 1 d . . . . .
H13A H 0.469866 -0.408918 0.564855 0.139 Uiso 1 1 calc R U . . .
H13B H 0.502128 -0.298914 0.558239 0.139 Uiso 1 1 calc R U . . .
H13C H 0.459204 -0.34099 0.515858 0.139 Uiso 1 1 calc R U . . .
C14 C 0.49994(17) -0.0918(10) 0.6571(2) 0.0462(16) Uani 1 1 d . . . . .
C15 C 0.4635(2) -0.0453(14) 0.6582(3) 0.088(3) Uani 1 1 d . . . . .
H15A H 0.466554 -0.109551 0.685253 0.131 Uiso 1 1 calc R U . . .
H15B H 0.440759 -0.108911 0.631709 0.131 Uiso 1 1 calc R U . . .
H15C H 0.45999 0.112498 0.658398 0.131 Uiso 1 1 calc R U . . .
C16 C 0.5057(2) -0.3423(12) 0.6579(3) 0.091(3) Uani 1 1 d . . . . .
H16A H 0.529631 -0.373635 0.658448 0.136 Uiso 1 1 calc R U . . .
H16B H 0.483464 -0.407557 0.631118 0.136 Uiso 1 1 calc R U . . .
H16C H 0.50782 -0.403821 0.684665 0.136 Uiso 1 1 calc R U . . .
C17 C 0.5341(2) 0.0091(12) 0.6992(2) 0.073(2) Uani 1 1 d . . . . .
H17A H 0.531608 0.168072 0.697346 0.11 Uiso 1 1 calc R U . . .
H17B H 0.558485 -0.033162 0.701837 0.11 Uiso 1 1 calc R U . . .
H17C H 0.534152 -0.042691 0.725413 0.11 Uiso 1 1 calc R U . . .
C18 C 0.77904(16) 0.9747(10) 0.66379(18) 0.0376(14) Uani 1 1 d D . . . .
C19 C 0.75146(15) 0.9348(10) 0.67721(17) 0.0337(14) Uani 1 1 d . . . . .
C20 C 0.73052(16) 0.7377(10) 0.66769(17) 0.0377(15) Uani 1 1 d . . . . .
H20 H 0.735309 0.623461 0.653132 0.045 Uiso 1 1 calc R U . . .
C21 C 0.70352(16) 0.7080(10) 0.67899(17) 0.0372(14) Uani 1 1 d . . . . .
H21 H 0.690032 0.573071 0.671872 0.045 Uiso 1 1 calc R U . . .
C22 C 0.69490(15) 0.8681(10) 0.70063(17) 0.0348(14) Uani 1 1 d . . . . .
C23 C 0.71676(15) 1.0650(10) 0.71117(17) 0.0342(14) Uani 1 1 d . . . . .
H23 H 0.712571 1.178124 0.726455 0.041 Uiso 1 1 calc R U . . .
C24 C 0.74338(15) 1.0934(9) 0.69974(17) 0.0353(14) Uani 1 1 d . . . . .
H24 H 0.757263 1.227096 0.707337 0.042 Uiso 1 1 calc R U . . .
C25 C 0.64655(18) 0.6363(10) 0.7010(2) 0.0523(18) Uani 1 1 d . . . . .
H25A H 0.634999 0.602037 0.669227 0.078 Uiso 1 1 calc R U . . .
H25B H 0.625885 0.650348 0.707193 0.078 Uiso 1 1 calc R U . . .
H25C H 0.664353 0.51924 0.719341 0.078 Uiso 1 1 calc R U . . .
C26 C 0.65934(17) 1.0044(10) 0.7341(2) 0.0498(17) Uani 1 1 d . . . . .
H26A H 0.683661 1.051847 0.760984 0.075 Uiso 1 1 calc R U . . .
H26B H 0.641866 0.945104 0.74271 0.075 Uiso 1 1 calc R U . . .
H26C H 0.646845 1.128918 0.714062 0.075 Uiso 1 1 calc R U . . .
C27 C 0.88069(16) 0.8778(10) 0.6791(2) 0.0426(16) Uani 1 1 d . . . . .
C28 C 0.88194(17) 0.6279(10) 0.6786(2) 0.0577(19) Uani 1 1 d . . . . .
H28A H 0.881202 0.578816 0.651839 0.087 Uiso 1 1 calc R U . . .
H28B H 0.85944 0.56887 0.678418 0.087 Uiso 1 1 calc R U . . .
H28C H 0.905965 0.576404 0.705394 0.087 Uiso 1 1 calc R U . . .
C29 C 0.88480(18) 0.9528(11) 0.7230(2) 0.0586(19) Uani 1 1 d . . . . .
H29A H 0.863755 0.889752 0.725161 0.088 Uiso 1 1 calc R U . . .
H29B H 0.883311 1.112094 0.72318 0.088 Uiso 1 1 calc R U . . .
H29C H 0.909953 0.904507 0.748438 0.088 Uiso 1 1 calc R U . . .
C30 C 0.91548(18) 0.9726(11) 0.6784(2) 0.064(2) Uani 1 1 d . . . . .
H30A H 0.939805 0.930842 0.705923 0.096 Uiso 1 1 calc R U . . .
H30B H 0.913436 1.131779 0.676504 0.096 Uiso 1 1 calc R U . . .
H30C H 0.915314 0.915562 0.65246 0.096 Uiso 1 1 calc R U . . .
C31 C 0.82386(18) 0.9459(10) 0.5758(2) 0.0446(16) Uani 1 1 d . . . . .
C32 C 0.7832(2) 1.0263(11) 0.5438(2) 0.068(2) Uani 1 1 d . . . . .
H32A H 0.777415 1.018386 0.51312 0.102 Uiso 1 1 calc R U . . .
H32B H 0.780924 1.177575 0.550943 0.102 Uiso 1 1 calc R U . . .
H32C H 0.764644 0.935371 0.54632 0.102 Uiso 1 1 calc R U . . .
C33 C 0.8266(2) 0.7029(10) 0.5666(2) 0.0589(19) Uani 1 1 d . . . . .
H33A H 0.810764 0.616166 0.574268 0.088 Uiso 1 1 calc R U . . .
H33B H 0.853819 0.655299 0.584891 0.088 Uiso 1 1 calc R U . . .
H33C H 0.817112 0.683042 0.534877 0.088 Uiso 1 1 calc R U . . .
C34 C 0.8513(2) 1.0797(11) 0.5674(2) 0.062(2) Uani 1 1 d . . . . .
H34A H 0.841543 1.078318 0.535376 0.093 Uiso 1 1 calc R U . . .
H34B H 0.877416 1.015926 0.584194 0.093 Uiso 1 1 calc R U . . .
H34C H 0.852357 1.230085 0.577281 0.093 Uiso 1 1 calc R U . . .
P1 P 0.55217(5) -0.0046(3) 0.61730(6) 0.0551(5) Uani 1 1 d . . . . .
P2 P 0.49556(5) 0.0645(3) 0.60864(6) 0.0471(5) Uani 1 1 d . . . . .
P3 P 0.79023(5) 0.8086(3) 0.63461(6) 0.0458(5) Uani 1 1 d . . . . .
P4 P 0.83437(4) 1.0139(3) 0.63374(5) 0.0403(4) Uani 1 1 d . . . . .
N1 N 0.67769(14) 0.4621(8) 0.56762(17) 0.0471(14) Uani 1 1 d . . . . .
N2 N 0.66767(13) 0.8379(8) 0.71139(16) 0.0409(12) Uani 1 1 d . . . . .
H1 H 0.5423(12) 0.353(6) 0.5952(19) 0.07(2) Uiso 1 1 d D . . . .
H18 H 0.7883(12) 1.120(3) 0.6698(15) 0.025(14) Uiso 1 1 d D . . . .



#----------------------------------------------------------------------------#
#                   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
C1 C2 1.439(8) . ?
C1 P1 1.705(7) . ?
C1 H1 0.950(2) . ?
C2 C3 1.394(7) . ?
C2 C7 1.397(8) . ?
C3 C4 1.382(7) . ?
C3 H3 0.95 . ?
C4 C5 1.427(8) . ?
C4 H4 0.95 . ?
C5 N1 1.376(7) . ?
C5 C6 1.383(7) . ?
C6 C7 1.376(8) . ?
C6 H6 0.95 . ?
C7 H7 0.95 . ?
C8 N1 1.437(7) . ?
C8 H8A 0.98 . ?
C8 H8B 0.98 . ?
C8 H8C 0.98 . ?
C9 N1 1.443(7) . ?
C9 H9A 0.98 . ?
C9 H9B 0.98 . ?
C9 H9C 0.98 . ?
C10 C11 1.514(9) . ?
C10 C12 1.522(9) . ?
C10 C13 1.539(9) . ?
C10 P2 1.878(7) . ?
C11 H11A 0.98 . ?
C11 H11B 0.98 . ?
C11 H11C 0.98 . ?
C12 H12A 0.98 . ?
C12 H12B 0.98 . ?
C12 H12C 0.98 . ?
C13 H13A 0.98 . ?
C13 H13B 0.98 . ?
C13 H13C 0.98 . ?
C14 C17 1.522(8) . ?
C14 C15 1.529(8) . ?
C14 C16 1.554(9) . ?
C14 P2 1.887(7) . ?
C15 H15A 0.98 . ?
C15 H15B 0.98 . ?
C15 H15C 0.98 . ?
C16 H16A 0.98 . ?
C16 H16B 0.98 . ?
C16 H16C 0.98 . ?
C17 H17A 0.98 . ?
C17 H17B 0.98 . ?
C17 H17C 0.98 . ?
C18 C19 1.454(7) . ?
C18 P3 1.677(6) . ?
C18 H18 0.950(2) . ?
C19 C24 1.404(7) . ?
C19 C20 1.413(7) . ?
C20 C21 1.367(7) . ?
C20 H20 0.95 . ?
C21 C22 1.401(7) . ?
C21 H21 0.95 . ?
C22 N2 1.363(6) . ?
C22 C23 1.427(8) . ?
C23 C24 1.354(7) . ?
C23 H23 0.95 . ?
C24 H24 0.95 . ?
C25 N2 1.437(7) . ?
C25 H25A 0.98 . ?
C25 H25B 0.98 . ?
C25 H25C 0.98 . ?
C26 N2 1.449(7) . ?
C26 H26A 0.98 . ?
C26 H26B 0.98 . ?
C26 H26C 0.98 . ?
C27 C28 1.536(8) . ?
C27 C29 1.538(8) . ?
C27 C30 1.542(8) . ?
C27 P4 1.894(6) . ?
C28 H28A 0.98 . ?
C28 H28B 0.98 . ?
C28 H28C 0.98 . ?
C29 H29A 0.98 . ?
C29 H29B 0.98 . ?
C29 H29C 0.98 . ?
C30 H30A 0.98 . ?
C30 H30B 0.98 . ?
C30 H30C 0.98 . ?
C31 C32 1.503(8) . ?
C31 C34 1.537(8) . ?
C31 C33 1.544(8) . ?
C31 P4 1.901(6) . ?
C32 H32A 0.98 . ?
C32 H32B 0.98 . ?
C32 H32C 0.98 . ?
C33 H33A 0.98 . ?
C33 H33B 0.98 . ?
C33 H33C 0.98 . ?
C34 H34A 0.98 . ?
C34 H34B 0.98 . ?
C34 H34C 0.98 . ?
P1 P2 2.195(2) . ?
P3 P4 2.207(2) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 P1 126.8(5) . . ?
C2 C1 H1 117(4) . . ?
P1 C1 H1 116(4) . . ?
C3 C2 C7 116.5(6) . . ?
C3 C2 C1 123.6(6) . . ?
C7 C2 C1 119.8(6) . . ?
C4 C3 C2 121.9(6) . . ?
C4 C3 H3 119.1 . . ?
C2 C3 H3 119.1 . . ?
C3 C4 C5 120.6(6) . . ?
C3 C4 H4 119.7 . . ?
C5 C4 H4 119.7 . . ?
N1 C5 C6 121.6(6) . . ?
N1 C5 C4 121.3(5) . . ?
C6 C5 C4 117.1(6) . . ?
C7 C6 C5 121.3(6) . . ?
C7 C6 H6 119.3 . . ?
C5 C6 H6 119.3 . . ?
C6 C7 C2 122.5(6) . . ?
C6 C7 H7 118.7 . . ?
C2 C7 H7 118.7 . . ?
N1 C8 H8A 109.5 . . ?
N1 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
N1 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N1 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C11 C10 C12 107.9(6) . . ?
C11 C10 C13 107.8(6) . . ?
C12 C10 C13 109.2(7) . . ?
C11 C10 P2 105.9(5) . . ?
C12 C10 P2 109.4(5) . . ?
C13 C10 P2 116.3(5) . . ?
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 . . ?
C10 C13 H13A 109.5 . . ?
C10 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C10 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C17 C14 C15 106.7(6) . . ?
C17 C14 C16 109.5(6) . . ?
C15 C14 C16 108.9(6) . . ?
C17 C14 P2 105.9(4) . . ?
C15 C14 P2 107.8(5) . . ?
C16 C14 P2 117.4(5) . . ?
C14 C15 H15A 109.5 . . ?
C14 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C14 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C14 C17 H17A 109.5 . . ?
C14 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C14 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C19 C18 P3 127.5(5) . . ?
C19 C18 H18 112(3) . . ?
P3 C18 H18 120(3) . . ?
C24 C19 C20 115.8(5) . . ?
C24 C19 C18 121.6(5) . . ?
C20 C19 C18 122.6(5) . . ?
C21 C20 C19 121.4(5) . . ?
C21 C20 H20 119.3 . . ?
C19 C20 H20 119.3 . . ?
C20 C21 C22 122.7(6) . . ?
C20 C21 H21 118.6 . . ?
C22 C21 H21 118.6 . . ?
N2 C22 C21 122.3(6) . . ?
N2 C22 C23 121.9(5) . . ?
C21 C22 C23 115.7(5) . . ?
C24 C23 C22 121.1(5) . . ?
C24 C23 H23 119.4 . . ?
C22 C23 H23 119.4 . . ?
C23 C24 C19 123.2(6) . . ?
C23 C24 H24 118.4 . . ?
C19 C24 H24 118.4 . . ?
N2 C25 H25A 109.5 . . ?
N2 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
N2 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
N2 C26 H26A 109.5 . . ?
N2 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
N2 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C28 C27 C29 108.9(5) . . ?
C28 C27 C30 110.0(5) . . ?
C29 C27 C30 107.3(5) . . ?
C28 C27 P4 117.1(4) . . ?
C29 C27 P4 104.1(4) . . ?
C30 C27 P4 109.0(4) . . ?
C27 C28 H28A 109.5 . . ?
C27 C28 H28B 109.5 . . ?
H28A C28 H28B 109.5 . . ?
C27 C28 H28C 109.5 . . ?
H28A C28 H28C 109.5 . . ?
H28B C28 H28C 109.5 . . ?
C27 C29 H29A 109.5 . . ?
C27 C29 H29B 109.5 . . ?
H29A C29 H29B 109.5 . . ?
C27 C29 H29C 109.5 . . ?
H29A C29 H29C 109.5 . . ?
H29B C29 H29C 109.5 . . ?
C27 C30 H30A 109.5 . . ?
C27 C30 H30B 109.5 . . ?
H30A C30 H30B 109.5 . . ?
C27 C30 H30C 109.5 . . ?
H30A C30 H30C 109.5 . . ?
H30B C30 H30C 109.5 . . ?
C32 C31 C34 107.3(5) . . ?
C32 C31 C33 109.5(6) . . ?
C34 C31 C33 109.4(5) . . ?
C32 C31 P4 105.3(4) . . ?
C34 C31 P4 108.8(4) . . ?
C33 C31 P4 116.1(4) . . ?
C31 C32 H32A 109.5 . . ?
C31 C32 H32B 109.5 . . ?
H32A C32 H32B 109.5 . . ?
C31 C32 H32C 109.5 . . ?
H32A C32 H32C 109.5 . . ?
H32B C32 H32C 109.5 . . ?
C31 C33 H33A 109.5 . . ?
C31 C33 H33B 109.5 . . ?
H33A C33 H33B 109.5 . . ?
C31 C33 H33C 109.5 . . ?
H33A C33 H33C 109.5 . . ?
H33B C33 H33C 109.5 . . ?
C31 C34 H34A 109.5 . . ?
C31 C34 H34B 109.5 . . ?
H34A C34 H34B 109.5 . . ?
C31 C34 H34C 109.5 . . ?
H34A C34 H34C 109.5 . . ?
H34B C34 H34C 109.5 . . ?
C1 P1 P2 99.2(2) . . ?
C10 P2 C14 111.6(3) . . ?
C10 P2 P1 100.9(2) . . ?
C14 P2 P1 101.1(2) . . ?
C18 P3 P4 98.7(2) . . ?
C27 P4 C31 111.4(3) . . ?
C27 P4 P3 100.6(2) . . ?
C31 P4 P3 100.0(2) . . ?
C5 N1 C8 121.4(5) . . ?
C5 N1 C9 120.3(5) . . ?
C8 N1 C9 117.8(5) . . ?
C22 N2 C25 120.6(5) . . ?
C22 N2 C26 121.7(5) . . ?
C25 N2 C26 117.7(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 C1 C2 C3 -3.1(9) . . . . ?
P1 C1 C2 C7 176.0(5) . . . . ?
C7 C2 C3 C4 -2.1(8) . . . . ?
C1 C2 C3 C4 177.0(5) . . . . ?
C2 C3 C4 C5 0.6(8) . . . . ?
C3 C4 C5 N1 179.5(5) . . . . ?
C3 C4 C5 C6 1.5(8) . . . . ?
N1 C5 C6 C7 -180.0(5) . . . . ?
C4 C5 C6 C7 -2.0(8) . . . . ?
C5 C6 C7 C2 0.4(9) . . . . ?
C3 C2 C7 C6 1.6(9) . . . . ?
C1 C2 C7 C6 -177.5(5) . . . . ?
P3 C18 C19 C24 -176.7(4) . . . . ?
P3 C18 C19 C20 1.9(8) . . . . ?
C24 C19 C20 C21 1.5(8) . . . . ?
C18 C19 C20 C21 -177.1(5) . . . . ?
C19 C20 C21 C22 -0.2(8) . . . . ?
C20 C21 C22 N2 179.4(5) . . . . ?
C20 C21 C22 C23 -1.2(8) . . . . ?
N2 C22 C23 C24 -179.2(5) . . . . ?
C21 C22 C23 C24 1.4(8) . . . . ?
C22 C23 C24 C19 -0.1(8) . . . . ?
C20 C19 C24 C23 -1.3(8) . . . . ?
C18 C19 C24 C23 177.3(5) . . . . ?
C2 C1 P1 P2 -174.1(5) . . . . ?
C11 C10 P2 C14 176.8(4) . . . . ?
C12 C10 P2 C14 60.8(6) . . . . ?
C13 C10 P2 C14 -63.5(6) . . . . ?
C11 C10 P2 P1 -76.5(5) . . . . ?
C12 C10 P2 P1 167.4(5) . . . . ?
C13 C10 P2 P1 43.1(6) . . . . ?
C17 C14 P2 C10 168.0(4) . . . . ?
C15 C14 P2 C10 -78.1(5) . . . . ?
C16 C14 P2 C10 45.3(6) . . . . ?
C17 C14 P2 P1 61.5(5) . . . . ?
C15 C14 P2 P1 175.4(4) . . . . ?
C16 C14 P2 P1 -61.2(5) . . . . ?
C19 C18 P3 P4 -178.9(5) . . . . ?
C28 C27 P4 C31 -60.6(5) . . . . ?
C29 C27 P4 C31 179.2(4) . . . . ?
C30 C27 P4 C31 65.0(5) . . . . ?
C28 C27 P4 P3 44.7(5) . . . . ?
C29 C27 P4 P3 -75.6(4) . . . . ?
C30 C27 P4 P3 170.2(4) . . . . ?
C6 C5 N1 C8 -172.9(5) . . . . ?
C4 C5 N1 C8 9.2(8) . . . . ?
C6 C5 N1 C9 -1.4(8) . . . . ?
C4 C5 N1 C9 -179.3(5) . . . . ?
C21 C22 N2 C25 0.4(8) . . . . ?
C23 C22 N2 C25 -179.0(5) . . . . ?
C21 C22 N2 C26 179.4(5) . . . . ?
C23 C22 N2 C26 0.1(8) . . . . ?



# END of CIF
####################################################################### 
# 
# 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_3f
_database_code_depnum_ccdc_archive 'CCDC 2087482'
loop_
_audit_author_name
_audit_author_address
'Lukasz Ponikiewski'
;Gdansk University of Technology
Poland
;
_audit_update_record             
;
2021-06-02 deposited with the CCDC.	2021-06-21 downloaded from the CCDC.
;

_audit_creation_date             2021-05-20T10:41:12-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'C19 H32 P2'
_chemical_formula_sum            'C19 H32 P2'
_chemical_formula_weight         322.38
_chemical_absolute_configuration unk

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_Int_Tables_number      19
loop_
_symmetry_equiv_pos_as_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'

_cell_length_a                   10.1040(2)
_cell_length_b                   12.2845(4)
_cell_length_c                   15.8640(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1969.08(9)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    19521
_cell_measurement_theta_min      2.39
_cell_measurement_theta_max      29.61
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.21
_exptl_crystal_density_diffrn    1.087
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             704

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.215
_exptl_absorpt_correction_type   none
_shelx_estimated_absorpt_T_min   0.954
_shelx_estimated_absorpt_T_max   0.956

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_standards_number         0
_diffrn_measurement_device       '2-circle diffractometer'
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_type            'STOE Imaging Plate'
_diffrn_detector_area_resol_mean 6.67
_diffrn_source                   'GeniX Mo, 0.05 x 0.05 mm2 microfocus'
_diffrn_source_type              ?
_diffrn_source_target            ?
_diffrn_source_voltage           50
_diffrn_source_current           1.000
_diffrn_source_power             0.050
_diffrn_radiation_monochromator  'parabolic x-ray mirror'
_diffrn_radiation_polarisn_norm  270
_diffrn_radiation_collimation    '0.6 mm diameter'
_diffrn_measurement_method       'rotation method, ω scans'
_diffrn_measurement_details      
; 154 frames, detector distance = 100 mm
;
_diffrn_reflns_av_R_equivalents  0.0224
_diffrn_reflns_av_unetI/netI     0.024
_diffrn_reflns_number            12902
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.39
_diffrn_reflns_theta_max         29.162
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.997
_reflns_Friedel_fraction_full    1
_reflns_Friedel_fraction_max     0.995
_reflns_Friedel_coverage         0.772
_reflns_number_total             5299
_reflns_number_gt                4899
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       
;
X-Area WinXpose 2.0.22.0 (STOE, 2016)
;
_computing_cell_refinement       
;
X-Area Recipe 1.33.0.0 (STOE, 2015)
;
_computing_data_reduction        
;
X-Area Integrate 1.72.0.0 (STOE, 2018)
X-Area X-Red32 1.63.4.0 (STOE, 2017) 
;
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0631P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         5299
_refine_ls_number_parameters     260
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0354
_refine_ls_R_factor_gt           0.0319
_refine_ls_wR_factor_ref         0.0848
_refine_ls_wR_factor_gt          0.0831
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.053
_refine_ls_shift/su_max          0.018
_refine_ls_shift/su_mean         0.001
_refine_ls_abs_structure_details 
;
 Flack x determined using 2024 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.08(5)
_refine_diff_density_max         0.465
_refine_diff_density_min         -0.147
_refine_diff_density_rms         0.049

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 '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'

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
C1 C 0.51939(15) 0.42461(14) 0.61291(10) 0.0239(3) Uani 1 1 d . . . . .
C2 C 0.42910(16) 0.34242(15) 0.56730(11) 0.0279(3) Uani 1 1 d . . . . .
C3 C 0.50589(19) 0.26488(17) 0.50984(14) 0.0376(4) Uani 1 1 d . . . . .
H3A H 0.554222 0.30703 0.467377 0.056 Uiso 1 1 calc R U . . .
H3B H 0.443915 0.2154 0.481729 0.056 Uiso 1 1 calc R U . . .
H3C H 0.568708 0.222536 0.543603 0.056 Uiso 1 1 calc R U . . .
C4 C 0.3507(2) 0.27376(16) 0.63117(13) 0.0354(4) Uani 1 1 d . . . . .
H4A H 0.412408 0.234559 0.667902 0.053 Uiso 1 1 calc R U . . .
H4B H 0.295039 0.221363 0.60094 0.053 Uiso 1 1 calc R U . . .
H4C H 0.294641 0.321609 0.665363 0.053 Uiso 1 1 calc R U . . .
C5 C 0.33107(19) 0.40746(17) 0.51263(13) 0.0375(4) Uani 1 1 d . . . . .
H5A H 0.275655 0.453133 0.548964 0.056 Uiso 1 1 calc R U . . .
H5B H 0.274878 0.356964 0.480916 0.056 Uiso 1 1 calc R U . . .
H5C H 0.380293 0.453685 0.473237 0.056 Uiso 1 1 calc R U . . .
C6 C 0.45256(15) 0.49669(14) 0.67487(11) 0.0242(3) Uani 1 1 d . . . . .
C7 C 0.43908(17) 0.46606(16) 0.75914(11) 0.0304(4) Uani 1 1 d . . . . .
H7 H 0.474247 0.398399 0.777557 0.036 Uiso 1 1 calc R U . . .
C8 C 0.3749(2) 0.53329(17) 0.81636(12) 0.0366(4) Uani 1 1 d . . . . .
H8 H 0.366471 0.511319 0.873525 0.044 Uiso 1 1 calc R U . . .
C9 C 0.32319(19) 0.63194(17) 0.79068(12) 0.0369(4) Uani 1 1 d . . . . .
H9 H 0.278823 0.677624 0.829876 0.044 Uiso 1 1 calc R U . . .
C10 C 0.33652(19) 0.66381(16) 0.70725(13) 0.0359(4) Uani 1 1 d . . . . .
H10 H 0.301577 0.731702 0.689174 0.043 Uiso 1 1 calc R U . . .
C11 C 0.40081(16) 0.59666(14) 0.65027(12) 0.0299(3) Uani 1 1 d . . . . .
H11 H 0.409694 0.619339 0.593295 0.036 Uiso 1 1 calc R U . . .
C12 C 0.89319(18) 0.51331(15) 0.72423(12) 0.0307(4) Uani 1 1 d . . . . .
C16 C 0.82064(18) 0.65723(16) 0.56941(11) 0.0315(4) Uani 1 1 d . . . . .
P1 P 0.68260(4) 0.43120(4) 0.58910(3) 0.02616(11) Uani 1 1 d . . . . .
P2 P 0.75228(4) 0.57544(3) 0.66132(3) 0.02366(10) Uani 1 1 d . . . . .
C13 C 0.9479(8) 0.6010(9) 0.7847(5) 0.0437(17) Uani 0.563(10) 1 d . . P A 1
H13A H 0.875369 0.630873 0.818556 0.065 Uiso 0.563(10) 1 calc R U P A 1
H13B H 0.988959 0.659585 0.751863 0.065 Uiso 0.563(10) 1 calc R U P A 1
H13C H 1.014182 0.568301 0.822018 0.065 Uiso 0.563(10) 1 calc R U P A 1
C14 C 1.0175(5) 0.4709(5) 0.6720(3) 0.0379(11) Uani 0.563(10) 1 d . . P A 1
H14A H 1.077396 0.431155 0.709676 0.057 Uiso 0.563(10) 1 calc R U P A 1
H14B H 1.064359 0.533069 0.647391 0.057 Uiso 0.563(10) 1 calc R U P A 1
H14C H 0.987368 0.422323 0.626961 0.057 Uiso 0.563(10) 1 calc R U P A 1
C15 C 0.8379(4) 0.4195(5) 0.7713(4) 0.0460(14) Uani 0.563(10) 1 d . . P A 1
H15A H 0.903771 0.392895 0.811734 0.069 Uiso 0.563(10) 1 calc R U P A 1
H15B H 0.815331 0.361161 0.731736 0.069 Uiso 0.563(10) 1 calc R U P A 1
H15C H 0.758164 0.442475 0.801636 0.069 Uiso 0.563(10) 1 calc R U P A 1
C17A C 0.8983(16) 0.7603(10) 0.6063(9) 0.0395(18) Uani 0.563(10) 1 d . . P A 1
H17A H 0.988283 0.738673 0.622146 0.059 Uiso 0.563(10) 1 calc R U P A 1
H17B H 0.85172 0.787965 0.656119 0.059 Uiso 0.563(10) 1 calc R U P A 1
H17C H 0.902438 0.817523 0.563334 0.059 Uiso 0.563(10) 1 calc R U P A 1
C18A C 0.8996(14) 0.5993(14) 0.5012(10) 0.043(2) Uani 0.563(10) 1 d . . P A 1
H18A H 0.916871 0.649806 0.45464 0.065 Uiso 0.563(10) 1 calc R U P A 1
H18B H 0.849021 0.536842 0.480274 0.065 Uiso 0.563(10) 1 calc R U P A 1
H18C H 0.983864 0.573979 0.524698 0.065 Uiso 0.563(10) 1 calc R U P A 1
C19A C 0.6952(13) 0.7057(14) 0.5243(10) 0.054(3) Uani 0.563(10) 1 d . . P A 1
H19A H 0.723353 0.754999 0.479122 0.081 Uiso 0.563(10) 1 calc R U P A 1
H19B H 0.64174 0.745987 0.565295 0.081 Uiso 0.563(10) 1 calc R U P A 1
H19C H 0.642484 0.646372 0.500287 0.081 Uiso 0.563(10) 1 calc R U P A 1
C13A C 0.9749(12) 0.6001(10) 0.7596(7) 0.045(2) Uani 0.437(10) 1 d . . P A 2
H13D H 1.020178 0.573371 0.810182 0.068 Uiso 0.437(10) 1 calc R U P A 2
H13E H 0.918741 0.662212 0.774551 0.068 Uiso 0.437(10) 1 calc R U P A 2
H13F H 1.040761 0.623022 0.717844 0.068 Uiso 0.437(10) 1 calc R U P A 2
C14A C 0.9667(8) 0.4233(7) 0.6869(4) 0.0456(18) Uani 0.437(10) 1 d . . P A 2
H14D H 1.008915 0.447759 0.634627 0.068 Uiso 0.437(10) 1 calc R U P A 2
H14E H 0.905872 0.363273 0.674491 0.068 Uiso 0.437(10) 1 calc R U P A 2
H14F H 1.034645 0.398415 0.72654 0.068 Uiso 0.437(10) 1 calc R U P A 2
C15A C 0.8091(6) 0.4653(5) 0.8026(4) 0.0384(14) Uani 0.437(10) 1 d . . P A 2
H15D H 0.745398 0.411474 0.781826 0.058 Uiso 0.437(10) 1 calc R U P A 2
H15E H 0.761593 0.524803 0.830494 0.058 Uiso 0.437(10) 1 calc R U P A 2
H15F H 0.869342 0.430664 0.842849 0.058 Uiso 0.437(10) 1 calc R U P A 2
C17 C 0.875(2) 0.7549(16) 0.6018(13) 0.059(5) Uani 0.437(10) 1 d . . P A 2
H17D H 0.91206 0.797819 0.555528 0.088 Uiso 0.437(10) 1 calc R U P A 2
H17E H 0.944422 0.737565 0.64256 0.088 Uiso 0.437(10) 1 calc R U P A 2
H17F H 0.804833 0.796863 0.629769 0.088 Uiso 0.437(10) 1 calc R U P A 2
C18 C 0.9276(17) 0.6008(15) 0.5156(13) 0.042(3) Uani 0.437(10) 1 d . . P A 2
H18D H 0.945398 0.644612 0.465225 0.063 Uiso 0.437(10) 1 calc R U P A 2
H18E H 0.896397 0.528512 0.498688 0.063 Uiso 0.437(10) 1 calc R U P A 2
H18F H 1.009033 0.593471 0.548685 0.063 Uiso 0.437(10) 1 calc R U P A 2
C19 C 0.701(2) 0.6796(18) 0.5187(12) 0.055(4) Uani 0.437(10) 1 d . . P A 2
H19D H 0.629672 0.703626 0.555873 0.083 Uiso 0.437(10) 1 calc R U P A 2
H19E H 0.674548 0.613208 0.489111 0.083 Uiso 0.437(10) 1 calc R U P A 2
H19F H 0.720979 0.736861 0.477565 0.083 Uiso 0.437(10) 1 calc R U P A 2



#----------------------------------------------------------------------------#
#                   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
C1 C6 1.485(2) . ?
C1 C2 1.541(2) . ?
C1 P1 1.6936(16) . ?
C2 C3 1.530(2) . ?
C2 C4 1.538(3) . ?
C2 C5 1.540(3) . ?
C3 H3A 0.98 . ?
C3 H3B 0.98 . ?
C3 H3C 0.98 . ?
C4 H4A 0.98 . ?
C4 H4B 0.98 . ?
C4 H4C 0.98 . ?
C5 H5A 0.98 . ?
C5 H5B 0.98 . ?
C5 H5C 0.98 . ?
C6 C11 1.391(2) . ?
C6 C7 1.395(2) . ?
C7 C8 1.388(3) . ?
C7 H7 0.95 . ?
C8 C9 1.381(3) . ?
C8 H8 0.95 . ?
C9 C10 1.387(3) . ?
C9 H9 0.95 . ?
C10 C11 1.386(2) . ?
C10 H10 0.95 . ?
C11 H11 0.95 . ?
C12 C14A 1.457(6) . ?
C12 C13A 1.461(12) . ?
C12 C15 1.482(4) . ?
C12 C13 1.545(9) . ?
C12 C14 1.592(5) . ?
C12 C15A 1.617(6) . ?
C12 P2 1.8988(18) . ?
C16 C17 1.41(2) . ?
C16 C19 1.473(19) . ?
C16 C18A 1.521(19) . ?
C16 C18 1.54(2) . ?
C16 C19A 1.573(13) . ?
C16 C17A 1.601(15) . ?
C16 P2 1.9006(18) . ?
P1 P2 2.2245(6) . ?
C13 H13A 0.98 . ?
C13 H13B 0.98 . ?
C13 H13C 0.98 . ?
C14 H14A 0.98 . ?
C14 H14B 0.98 . ?
C14 H14C 0.98 . ?
C15 H15A 0.98 . ?
C15 H15B 0.98 . ?
C15 H15C 0.98 . ?
C17A H17A 0.98 . ?
C17A H17B 0.98 . ?
C17A H17C 0.98 . ?
C18A H18A 0.98 . ?
C18A H18B 0.98 . ?
C18A H18C 0.98 . ?
C19A H19A 0.98 . ?
C19A H19B 0.98 . ?
C19A H19C 0.98 . ?
C13A H13D 0.98 . ?
C13A H13E 0.98 . ?
C13A H13F 0.98 . ?
C14A H14D 0.98 . ?
C14A H14E 0.98 . ?
C14A H14F 0.98 . ?
C15A H15D 0.98 . ?
C15A H15E 0.98 . ?
C15A H15F 0.98 . ?
C17 H17D 0.98 . ?
C17 H17E 0.98 . ?
C17 H17F 0.98 . ?
C18 H18D 0.98 . ?
C18 H18E 0.98 . ?
C18 H18F 0.98 . ?
C19 H19D 0.98 . ?
C19 H19E 0.98 . ?
C19 H19F 0.98 . ?

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
C6 C1 C2 115.60(13) . . ?
C6 C1 P1 124.17(12) . . ?
C2 C1 P1 120.20(12) . . ?
C3 C2 C4 108.20(16) . . ?
C3 C2 C5 108.28(15) . . ?
C4 C2 C5 108.91(15) . . ?
C3 C2 C1 112.79(14) . . ?
C4 C2 C1 110.79(14) . . ?
C5 C2 C1 107.77(14) . . ?
C2 C3 H3A 109.5 . . ?
C2 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
C2 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
C2 C4 H4A 109.5 . . ?
C2 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
C2 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
C2 C5 H5A 109.5 . . ?
C2 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C2 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C11 C6 C7 118.06(16) . . ?
C11 C6 C1 120.77(15) . . ?
C7 C6 C1 121.17(15) . . ?
C8 C7 C6 120.77(17) . . ?
C8 C7 H7 119.6 . . ?
C6 C7 H7 119.6 . . ?
C9 C8 C7 120.39(18) . . ?
C9 C8 H8 119.8 . . ?
C7 C8 H8 119.8 . . ?
C8 C9 C10 119.51(17) . . ?
C8 C9 H9 120.2 . . ?
C10 C9 H9 120.2 . . ?
C11 C10 C9 120.01(18) . . ?
C11 C10 H10 120 . . ?
C9 C10 H10 120 . . ?
C10 C11 C6 121.26(17) . . ?
C10 C11 H11 119.4 . . ?
C6 C11 H11 119.4 . . ?
C14A C12 C13A 114.9(5) . . ?
C15 C12 C13 111.4(4) . . ?
C15 C12 C14 107.7(3) . . ?
C13 C12 C14 105.6(3) . . ?
C14A C12 C15A 107.7(4) . . ?
C13A C12 C15A 105.5(4) . . ?
C14A C12 P2 118.3(2) . . ?
C13A C12 P2 109.4(5) . . ?
C15 C12 P2 107.15(19) . . ?
C13 C12 P2 108.3(4) . . ?
C14 C12 P2 116.74(19) . . ?
C15A C12 P2 99.0(2) . . ?
C17 C16 C19 110.8(13) . . ?
C17 C16 C18 108.2(10) . . ?
C19 C16 C18 110.8(10) . . ?
C18A C16 C19A 106.0(8) . . ?
C18A C16 C17A 111.9(7) . . ?
C19A C16 C17A 105.2(8) . . ?
C17 C16 P2 108.0(8) . . ?
C19 C16 P2 102.7(7) . . ?
C18A C16 P2 119.3(7) . . ?
C18 C16 P2 116.2(8) . . ?
C19A C16 P2 104.9(6) . . ?
C17A C16 P2 108.4(5) . . ?
C1 P1 P2 103.38(6) . . ?
C12 P2 C16 110.07(8) . . ?
C12 P2 P1 100.82(6) . . ?
C16 P2 P1 98.10(6) . . ?
C12 C13 H13A 109.5 . . ?
C12 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C12 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C12 C14 H14A 109.5 . . ?
C12 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C12 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C12 C15 H15A 109.5 . . ?
C12 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C12 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C16 C17A H17A 109.5 . . ?
C16 C17A H17B 109.5 . . ?
H17A C17A H17B 109.5 . . ?
C16 C17A H17C 109.5 . . ?
H17A C17A H17C 109.5 . . ?
H17B C17A H17C 109.5 . . ?
C16 C18A H18A 109.5 . . ?
C16 C18A H18B 109.5 . . ?
H18A C18A H18B 109.5 . . ?
C16 C18A H18C 109.5 . . ?
H18A C18A H18C 109.5 . . ?
H18B C18A H18C 109.5 . . ?
C16 C19A H19A 109.5 . . ?
C16 C19A H19B 109.5 . . ?
H19A C19A H19B 109.5 . . ?
C16 C19A H19C 109.5 . . ?
H19A C19A H19C 109.5 . . ?
H19B C19A H19C 109.5 . . ?
C12 C13A H13D 109.5 . . ?
C12 C13A H13E 109.5 . . ?
H13D C13A H13E 109.5 . . ?
C12 C13A H13F 109.5 . . ?
H13D C13A H13F 109.5 . . ?
H13E C13A H13F 109.5 . . ?
C12 C14A H14D 109.5 . . ?
C12 C14A H14E 109.5 . . ?
H14D C14A H14E 109.5 . . ?
C12 C14A H14F 109.5 . . ?
H14D C14A H14F 109.5 . . ?
H14E C14A H14F 109.5 . . ?
C12 C15A H15D 109.5 . . ?
C12 C15A H15E 109.5 . . ?
H15D C15A H15E 109.5 . . ?
C12 C15A H15F 109.5 . . ?
H15D C15A H15F 109.5 . . ?
H15E C15A H15F 109.5 . . ?
C16 C17 H17D 109.5 . . ?
C16 C17 H17E 109.5 . . ?
H17D C17 H17E 109.5 . . ?
C16 C17 H17F 109.5 . . ?
H17D C17 H17F 109.5 . . ?
H17E C17 H17F 109.5 . . ?
C16 C18 H18D 109.5 . . ?
C16 C18 H18E 109.5 . . ?
H18D C18 H18E 109.5 . . ?
C16 C18 H18F 109.5 . . ?
H18D C18 H18F 109.5 . . ?
H18E C18 H18F 109.5 . . ?
C16 C19 H19D 109.5 . . ?
C16 C19 H19E 109.5 . . ?
H19D C19 H19E 109.5 . . ?
C16 C19 H19F 109.5 . . ?
H19D C19 H19F 109.5 . . ?
H19E C19 H19F 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
C6 C1 C2 C3 -175.37(16) . . . . ?
P1 C1 C2 C3 6.4(2) . . . . ?
C6 C1 C2 C4 -53.9(2) . . . . ?
P1 C1 C2 C4 127.88(14) . . . . ?
C6 C1 C2 C5 65.15(18) . . . . ?
P1 C1 C2 C5 -113.06(15) . . . . ?
C2 C1 C6 C11 -90.23(19) . . . . ?
P1 C1 C6 C11 87.90(18) . . . . ?
C2 C1 C6 C7 89.38(19) . . . . ?
P1 C1 C6 C7 -92.49(18) . . . . ?
C11 C6 C7 C8 0.5(2) . . . . ?
C1 C6 C7 C8 -179.12(16) . . . . ?
C6 C7 C8 C9 0.0(3) . . . . ?
C7 C8 C9 C10 -0.4(3) . . . . ?
C8 C9 C10 C11 0.3(3) . . . . ?
C9 C10 C11 C6 0.2(3) . . . . ?
C7 C6 C11 C10 -0.6(2) . . . . ?
C1 C6 C11 C10 179.02(16) . . . . ?
C6 C1 P1 P2 -5.01(15) . . . . ?
C2 C1 P1 P2 173.03(12) . . . . ?
C14A C12 P2 C16 -71.8(5) . . . . ?
C13A C12 P2 C16 62.4(5) . . . . ?
C15 C12 P2 C16 -158.2(3) . . . . ?
C13 C12 P2 C16 81.6(4) . . . . ?
C14 C12 P2 C16 -37.3(3) . . . . ?
C15A C12 P2 C16 172.5(3) . . . . ?
C14A C12 P2 P1 31.1(5) . . . . ?
C13A C12 P2 P1 165.3(5) . . . . ?
C15 C12 P2 P1 -55.3(3) . . . . ?
C13 C12 P2 P1 -175.5(3) . . . . ?
C14 C12 P2 P1 65.5(3) . . . . ?
C15A C12 P2 P1 -84.7(3) . . . . ?



# END of CIF
####################################################################### 
# 
# 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_5
_database_code_depnum_ccdc_archive 'CCDC 2077819'
loop_
_audit_author_name
_audit_author_address
'Lukasz Ponikiewski'
;Gdansk University of Technology
Poland
;
_audit_update_record             
;
2021-04-23 deposited with the CCDC.	2021-06-21 downloaded from the CCDC.
;

_audit_creation_date             2021-01-14T12:28:06-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'C24 H72 Li8 O8 Si8'
_chemical_formula_sum            'C24 H72 Li8 O8 Si8'
_chemical_formula_weight         769.05
_chemical_absolute_configuration unk

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_H-M   'I -4'
_symmetry_space_group_name_Hall  'I -4'
_symmetry_Int_Tables_number      82
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'y, -x, -z'
'-y, x, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1/2, -y+1/2, z+1/2'
'y+1/2, -x+1/2, -z+1/2'
'-y+1/2, x+1/2, -z+1/2'

_cell_length_a                   13.6438(4)
_cell_length_b                   13.6438(4)
_cell_length_c                   13.3861(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2491.87(16)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    13109
_cell_measurement_theta_min      4.58
_cell_measurement_theta_max      66.94
_cell_measurement_wavelength     1.54186

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.14
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_exptl_crystal_density_diffrn    1.025
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             832

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    2.283
_exptl_absorpt_correction_type   integration
_exptl_absorpt_process_details   
;
STOE X-Red32, absorption correction by Gaussian integration, analogous to
P. Coppens, "The Evaluation of Absorption and Extinction in Single-Crystal
Structure Analysis", published in
F. R. Ahmed (Editor), "Crystallographic Computing",
Munksgaard, Copenhagen (1970), 255 - 270
;
_exptl_absorpt_correction_T_min  0.7195
_exptl_absorpt_correction_T_max  0.7715
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-4 -2 3 0.0520
2 1 -1 0.0950
-1 0 -3 0.0780
3 1 7 0.0910
-3 6 1 0.0800
3 -6 1 0.0670
-2 -1 -1 0.0710
-1 2 3 0.0810
-1 2 -2 0.0890

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     1.54186
_diffrn_radiation_type           CuK\a
_diffrn_radiation_probe          x-ray
_diffrn_standards_number         0
__diffrn_measurement_device      '2-circle diffractometer'
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_type            'STOE Imaging Plate'
_diffrn_detector_area_resol_mean 6.67
_diffrn_source                   'GeniX Cu, 0.05 x 0.05 mm2 microfocus'
_diffrn_source_type              ?
_diffrn_source_target            ?
_diffrn_source_voltage           50
_diffrn_source_current           0.600
_diffrn_source_power             0.030
_diffrn_radiation_monochromator  'parabolic x-ray mirror'
_diffrn_radiation_polarisn_norm  270
_diffrn_radiation_collimation    '0.6 mm diameter'
_diffrn_measurement_method       'rotation method, ω scans'
_diffrn_measurement_details      
; 547 frames, detector distance = 45 mm
;
_diffrn_reflns_av_R_equivalents  0.0234
_diffrn_reflns_av_unetI/netI     0.0188
_diffrn_reflns_number            5864
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         4.583
_diffrn_reflns_theta_max         66.937
_diffrn_reflns_theta_full        66.937
_diffrn_measured_fraction_theta_full 0.962
_diffrn_measured_fraction_theta_max 0.962
_diffrn_reflns_Laue_measured_fraction_full 0.962
_diffrn_reflns_Laue_measured_fraction_max 0.962
_diffrn_reflns_point_group_measured_fraction_full 0.926
_diffrn_reflns_point_group_measured_fraction_max 0.926
_reflns_Friedel_fraction_full    0.885
_reflns_Friedel_fraction_max     0.885
_reflns_Friedel_coverage         0.832
_reflns_number_total             2044
_reflns_number_gt                1923
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       
;
X-Area WinXpose 2.0.22.0 (STOE, 2016)
;
_computing_cell_refinement       
;
X-Area Recipe 1.33.0.0 (STOE, 2015)
;
_computing_data_reduction        
;
X-Area Integrate 1.72.0.0 (STOE, 2018)
X-Area X-Red32 1.63.4.0 (STOE, 2017) 
;
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1067P)²+14.2635P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2044
_refine_ls_number_parameters     115
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.0862
_refine_ls_R_factor_gt           0.079
_refine_ls_wR_factor_ref         0.2209
_refine_ls_wR_factor_gt          0.2043
_refine_ls_goodness_of_fit_ref   1.178
_refine_ls_restrained_S_all      1.178
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 
;
 Flack x determined using 822 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.05(3)
_refine_diff_density_max         0.438
_refine_diff_density_min         -0.744
_refine_diff_density_rms         0.108

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Li Li 0.0008 0.0003 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Si Si 0.2541 0.3302 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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
Si2 Si 0.32492(18) 0.49222(18) 0.78305(18) 0.0362(6) Uani 1 1 d . . . . .
Si1 Si 0.22501(17) 0.52090(18) 0.4280(2) 0.0359(6) Uani 1 1 d . . . . .
O2 O 0.3947(5) 0.4772(5) 0.6877(5) 0.0393(15) Uani 1 1 d . . . . .
O1 O 0.3409(4) 0.5028(4) 0.4443(5) 0.0343(13) Uani 1 1 d . . . . .
C5 C 0.3290(8) 0.6250(9) 0.8205(8) 0.051(3) Uani 1 1 d . . . . .
H5A H 0.396455 0.643126 0.837438 0.076 Uiso 1 1 calc R U . . .
H5B H 0.286612 0.635329 0.878608 0.076 Uiso 1 1 calc R U . . .
H5C H 0.306034 0.665597 0.764814 0.076 Uiso 1 1 calc R U . . .
C3 C 0.1519(9) 0.4116(8) 0.4679(9) 0.055(3) Uani 1 1 d . . . . .
H3A H 0.169335 0.355216 0.42613 0.083 Uiso 1 1 calc R U . . .
H3B H 0.081886 0.425737 0.4605 0.083 Uiso 1 1 calc R U . . .
H3C H 0.166297 0.396518 0.537982 0.083 Uiso 1 1 calc R U . . .
C4 C 0.1959(8) 0.4584(8) 0.7571(8) 0.048(2) Uani 1 1 d . . . . .
H4A H 0.171515 0.497034 0.700645 0.071 Uiso 1 1 calc R U . . .
H4B H 0.155763 0.471832 0.816295 0.071 Uiso 1 1 calc R U . . .
H4C H 0.192189 0.388504 0.740792 0.071 Uiso 1 1 calc R U . . .
C6 C 0.3676(7) 0.4194(9) 0.8917(9) 0.051(3) Uani 1 1 d . . . . .
H6A H 0.357162 0.349525 0.878416 0.077 Uiso 1 1 calc R U . . .
H6B H 0.33058 0.438616 0.951305 0.077 Uiso 1 1 calc R U . . .
H6C H 0.437534 0.43155 0.902755 0.077 Uiso 1 1 calc R U . . .
C1 C 0.1845(8) 0.6317(8) 0.4991(9) 0.054(3) Uani 1 1 d . . . . .
H1A H 0.199638 0.623027 0.570127 0.082 Uiso 1 1 calc R U . . .
H1B H 0.113727 0.640652 0.49074 0.082 Uiso 1 1 calc R U . . .
H1C H 0.218995 0.689615 0.473706 0.082 Uiso 1 1 calc R U . . .
C2 C 0.1988(8) 0.5439(9) 0.2938(9) 0.054(3) Uani 1 1 d . . . . .
H2A H 0.216987 0.486009 0.254591 0.082 Uiso 1 1 calc R U . . .
H2B H 0.236784 0.600506 0.270913 0.082 Uiso 1 1 calc R U . . .
H2C H 0.128694 0.55716 0.285165 0.082 Uiso 1 1 calc R U . . .
Li2 Li 0.3833(11) 0.4291(12) 0.5570(12) 0.039(3) Uani 1 1 d . . . . .
Li1 Li 0.4797(13) 0.5877(13) 0.6749(13) 0.046(4) Uani 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   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
Si2 O2 1.606(7) . ?
Si2 C4 1.852(11) . ?
Si2 C6 1.855(12) . ?
Si2 C5 1.880(12) . ?
Si2 Li1 2.87(2) . ?
Si1 O1 1.615(6) . ?
Si1 C2 1.859(12) . ?
Si1 C1 1.870(12) . ?
Si1 C3 1.872(12) . ?
Si1 Li1 2.957(19) 4_656 ?
Si1 Li2 3.035(17) . ?
Si1 Li2 3.082(17) 3_566 ?
O2 Li2 1.876(17) . ?
O2 Li1 1.91(2) . ?
O2 Li1 1.936(17) 2_665 ?
O1 Li1 1.896(19) 4_656 ?
O1 Li2 1.903(18) . ?
O1 Li2 1.965(17) 3_566 ?
C5 H5A 0.98 . ?
C5 H5B 0.98 . ?
C5 H5C 0.98 . ?
C3 H3A 0.98 . ?
C3 H3B 0.98 . ?
C3 H3C 0.98 . ?
C4 H4A 0.98 . ?
C4 H4B 0.98 . ?
C4 H4C 0.98 . ?
C6 H6A 0.98 . ?
C6 H6B 0.98 . ?
C6 H6C 0.98 . ?
C1 H1A 0.98 . ?
C1 H1B 0.98 . ?
C1 H1C 0.98 . ?
C2 H2A 0.98 . ?
C2 H2B 0.98 . ?
C2 H2C 0.98 . ?
Li2 Li1 2.46(2) 2_665 ?
Li2 Li1 2.98(2) . ?
Li2 Li2 3.04(2) 3_566 ?
Li2 Li2 3.04(2) 4_656 ?
Li2 Li1 3.20(2) 4_656 ?
Li1 Li1 2.46(3) 2_665 ?

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
O2 Si2 C4 112.5(4) . . ?
O2 Si2 C6 111.7(4) . . ?
C4 Si2 C6 108.2(5) . . ?
O2 Si2 C5 108.5(4) . . ?
C4 Si2 C5 108.5(5) . . ?
C6 Si2 C5 107.3(5) . . ?
C4 Si2 Li1 135.8(5) . . ?
C6 Si2 Li1 114.0(5) . . ?
C5 Si2 Li1 71.1(5) . . ?
O1 Si1 C2 110.1(4) . . ?
O1 Si1 C1 110.1(4) . . ?
C2 Si1 C1 107.4(5) . . ?
O1 Si1 C3 111.2(4) . . ?
C2 Si1 C3 107.9(6) . . ?
C1 Si1 C3 110.0(5) . . ?
C2 Si1 Li1 75.4(5) . 4_656 ?
C1 Si1 Li1 130.2(5) . 4_656 ?
C3 Si1 Li1 116.2(5) . 4_656 ?
C2 Si1 Li2 139.1(5) . . ?
C1 Si1 Li2 104.8(5) . . ?
C3 Si1 Li2 83.6(5) . . ?
Li1 Si1 Li2 64.6(4) 4_656 . ?
C2 Si1 Li2 99.5(5) . 3_566 ?
C1 Si1 Li2 83.7(5) . 3_566 ?
C3 Si1 Li2 143.2(5) . 3_566 ?
Li1 Si1 Li2 48.0(5) 4_656 3_566 ?
Li2 Si1 Li2 59.7(6) . 3_566 ?
Si2 O2 Li2 137.5(6) . . ?
Si2 O2 Li1 109.3(6) . . ?
Li2 O2 Li1 104.1(8) . . ?
Si2 O2 Li1 130.8(7) . 2_665 ?
Li2 O2 Li1 80.3(8) . 2_665 ?
Li1 O2 Li1 79.4(8) . 2_665 ?
Si1 O1 Li1 114.5(6) . 4_656 ?
Si1 O1 Li2 119.0(6) . . ?
Li1 O1 Li2 115.0(8) 4_656 . ?
Si1 O1 Li2 118.5(6) . 3_566 ?
Li1 O1 Li2 79.0(7) 4_656 3_566 ?
Li2 O1 Li2 103.8(8) . 3_566 ?
Si2 C5 H5A 109.5 . . ?
Si2 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
Si2 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
Si1 C3 H3A 109.5 . . ?
Si1 C3 H3B 109.5 . . ?
H3A C3 H3B 109.5 . . ?
Si1 C3 H3C 109.5 . . ?
H3A C3 H3C 109.5 . . ?
H3B C3 H3C 109.5 . . ?
Si2 C4 H4A 109.5 . . ?
Si2 C4 H4B 109.5 . . ?
H4A C4 H4B 109.5 . . ?
Si2 C4 H4C 109.5 . . ?
H4A C4 H4C 109.5 . . ?
H4B C4 H4C 109.5 . . ?
Si2 C6 H6A 109.5 . . ?
Si2 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
Si2 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
Si1 C1 H1A 109.5 . . ?
Si1 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
Si1 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
Si1 C2 H2A 109.5 . . ?
Si1 C2 H2B 109.5 . . ?
H2A C2 H2B 109.5 . . ?
Si1 C2 H2C 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
O2 Li2 O1 125.4(9) . . ?
O2 Li2 O1 99.0(8) . 4_656 ?
O1 Li2 O1 123.9(8) . 4_656 ?
O2 Li2 Li1 50.9(6) . 2_665 ?
O1 Li2 Li1 142.2(9) . 2_665 ?
O1 Li2 Li1 49.2(5) 4_656 2_665 ?
O2 Li2 Li1 38.3(5) . . ?
O1 Li2 Li1 99.8(7) . . ?
O1 Li2 Li1 95.7(7) 4_656 . ?
Li1 Li2 Li1 52.6(7) 2_665 . ?
O2 Li2 Si1 116.4(7) . . ?
O1 Li2 Si1 27.7(3) . . ?
O1 Li2 Si1 144.1(7) 4_656 . ?
Li1 Li2 Si1 160.9(8) 2_665 . ?
Li1 Li2 Si1 108.4(6) . . ?
O2 Li2 Li2 99.0(7) . 3_566 ?
O1 Li2 Li2 38.8(6) . 3_566 ?
O1 Li2 Li2 110.4(5) 4_656 3_566 ?
Li1 Li2 Li2 104.1(6) 2_665 3_566 ?
Li1 Li2 Li2 64.2(5) . 3_566 ?
Si1 Li2 Li2 60.9(6) . 3_566 ?
O2 Li2 Li2 118.0(8) . 4_656 ?
O1 Li2 Li2 88.1(7) . 4_656 ?
O1 Li2 Li2 37.4(5) 4_656 4_656 ?
Li1 Li2 Li2 70.3(6) 2_665 4_656 ?
Li1 Li2 Li2 92.5(5) . 4_656 ?
Si1 Li2 Li2 113.5(8) . 4_656 ?
Li2 Li2 Li2 75.5(5) 3_566 4_656 ?
O2 Li2 Si1 102.7(7) . 4_656 ?
O1 Li2 Si1 131.2(7) . 4_656 ?
O1 Li2 Si1 27.4(3) 4_656 4_656 ?
Li1 Li2 Si1 63.4(5) 2_665 4_656 ?
Li1 Li2 Si1 115.7(6) . 4_656 ?
Si1 Li2 Si1 135.4(6) . 4_656 ?
Li2 Li2 Si1 134.8(6) 3_566 4_656 ?
Li2 Li2 Si1 59.4(5) 4_656 4_656 ?
O2 Li2 Li1 144.9(8) . 4_656 ?
O1 Li2 Li1 32.4(5) . 4_656 ?
O1 Li2 Li1 91.5(6) 4_656 4_656 ?
Li1 Li2 Li1 123.3(8) 2_665 4_656 ?
Li1 Li2 Li1 107.6(7) . 4_656 ?
Si1 Li2 Li1 56.5(4) . 4_656 ?
Li2 Li2 Li1 46.2(6) 3_566 4_656 ?
Li2 Li2 Li1 57.0(6) 4_656 4_656 ?
Si1 Li2 Li1 101.9(5) 4_656 4_656 ?
O1 Li1 O2 125.6(10) 3_566 . ?
O1 Li1 O2 99.4(9) 3_566 2_665 ?
O2 Li1 O2 99.7(8) . 2_665 ?
O1 Li1 Li1 117.6(6) 3_566 2_665 ?
O2 Li1 Li1 50.8(7) . 2_665 ?
O2 Li1 Li1 49.8(6) 2_665 2_665 ?
O1 Li1 Li2 51.7(6) 3_566 2_665 ?
O2 Li1 Li2 116.5(9) . 2_665 ?
O2 Li1 Li2 48.8(6) 2_665 2_665 ?
Li1 Li1 Li2 74.8(7) 2_665 2_665 ?
O1 Li1 Si2 141.2(8) 3_566 . ?
O2 Li1 Si2 31.8(4) . . ?
O2 Li1 Si2 113.5(8) 2_665 . ?
Li1 Li1 Si2 74.0(8) 2_665 . ?
Li2 Li1 Si2 147.2(8) 2_665 . ?
O1 Li1 Si1 29.8(3) 3_566 3_566 ?
O2 Li1 Si1 147.1(8) . 3_566 ?
O2 Li1 Si1 105.6(8) 2_665 3_566 ?
Li1 Li1 Si1 143.0(8) 2_665 3_566 ?
Li2 Li1 Si1 68.7(6) 2_665 3_566 ?
Si2 Li1 Si1 140.0(6) . 3_566 ?
O1 Li1 Li2 90.0(7) 3_566 . ?
O2 Li1 Li2 37.6(5) . . ?
O2 Li1 Li2 96.0(7) 2_665 . ?
Li1 Li1 Li2 52.6(7) 2_665 . ?
Li2 Li1 Li2 85.9(8) 2_665 . ?
Si2 Li1 Li2 67.3(5) . . ?
Si1 Li1 Li2 117.6(7) 3_566 . ?
O1 Li1 Li2 32.6(5) 3_566 3_566 ?
O2 Li1 Li2 93.0(7) . 3_566 ?
O2 Li1 Li2 109.4(8) 2_665 3_566 ?
Li1 Li1 Li2 99.7(5) 2_665 3_566 ?
Li2 Li1 Li2 63.5(6) 2_665 3_566 ?
Si2 Li1 Li2 112.7(6) . 3_566 ?
Si1 Li1 Li2 58.9(4) 3_566 3_566 ?
Li2 Li1 Li2 58.8(5) . 3_566 ?

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
C4 Si2 O2 Li2 -3.5(11) . . . . ?
C6 Si2 O2 Li2 118.3(10) . . . . ?
C5 Si2 O2 Li2 -123.6(10) . . . . ?
Li1 Si2 O2 Li2 -139.8(12) . . . . ?
C4 Si2 O2 Li1 136.3(7) . . . . ?
C6 Si2 O2 Li1 -101.9(7) . . . . ?
C5 Si2 O2 Li1 16.2(7) . . . . ?
C4 Si2 O2 Li1 -131.1(9) . . . 2_665 ?
C6 Si2 O2 Li1 -9.3(10) . . . 2_665 ?
C5 Si2 O2 Li1 108.8(10) . . . 2_665 ?
Li1 Si2 O2 Li1 92.6(11) . . . 2_665 ?
C2 Si1 O1 Li1 -13.7(8) . . . 4_656 ?
C1 Si1 O1 Li1 -132.0(7) . . . 4_656 ?
C3 Si1 O1 Li1 105.8(7) . . . 4_656 ?
Li2 Si1 O1 Li1 141.7(10) . . . 4_656 ?
Li2 Si1 O1 Li1 -90.6(9) 3_566 . . 4_656 ?
C2 Si1 O1 Li2 -155.4(7) . . . . ?
C1 Si1 O1 Li2 86.3(8) . . . . ?
C3 Si1 O1 Li2 -35.9(8) . . . . ?
Li1 Si1 O1 Li2 -141.7(10) 4_656 . . . ?
Li2 Si1 O1 Li2 127.7(7) 3_566 . . . ?
C2 Si1 O1 Li2 76.8(8) . . . 3_566 ?
C1 Si1 O1 Li2 -41.4(8) . . . 3_566 ?
C3 Si1 O1 Li2 -163.6(7) . . . 3_566 ?
Li1 Si1 O1 Li2 90.6(9) 4_656 . . 3_566 ?
Li2 Si1 O1 Li2 -127.7(7) . . . 3_566 ?
Si2 O2 Li2 O1 85.4(12) . . . . ?
Li1 O2 Li2 O1 -55.8(12) . . . . ?
Li1 O2 Li2 O1 -132.1(11) 2_665 . . . ?
Si2 O2 Li2 O1 -131.0(7) . . . 4_656 ?
Li1 O2 Li2 O1 87.9(8) . . . 4_656 ?
Li1 O2 Li2 O1 11.5(7) 2_665 . . 4_656 ?
Si2 O2 Li2 Li1 -142.5(10) . . . 2_665 ?
Li1 O2 Li2 Li1 76.4(8) . . . 2_665 ?
Si2 O2 Li2 Li1 141.1(11) . . . . ?
Li1 O2 Li2 Li1 -76.4(8) 2_665 . . . ?
Si2 O2 Li2 Si1 54.6(12) . . . . ?
Li1 O2 Li2 Si1 -86.5(8) . . . . ?
Li1 O2 Li2 Si1 -162.9(9) 2_665 . . . ?
Si2 O2 Li2 Li2 116.5(6) . . . 3_566 ?
Li1 O2 Li2 Li2 -24.6(8) . . . 3_566 ?
Li1 O2 Li2 Li2 -101.0(7) 2_665 . . 3_566 ?
Si2 O2 Li2 Li2 -165.2(6) . . . 4_656 ?
Li1 O2 Li2 Li2 53.6(10) . . . 4_656 ?
Li1 O2 Li2 Li2 -22.7(9) 2_665 . . 4_656 ?
Si2 O2 Li2 Si1 -103.3(8) . . . 4_656 ?
Li1 O2 Li2 Si1 115.5(6) . . . 4_656 ?
Li1 O2 Li2 Si1 39.2(7) 2_665 . . 4_656 ?
Si2 O2 Li2 Li1 123.2(12) . . . 4_656 ?
Li1 O2 Li2 Li1 -17.9(15) . . . 4_656 ?
Li1 O2 Li2 Li1 -94.3(16) 2_665 . . 4_656 ?



# END of CIF
####################################################################### 
# 
# 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_3e
_database_code_depnum_ccdc_archive 'CCDC 2077815'
loop_
_audit_author_name
_audit_author_address
'Lukasz Ponikiewski'
;Gdansk University of Technology
Poland
;
_audit_update_record             
;
2021-04-23 deposited with the CCDC.	2021-06-21 downloaded from the CCDC.
;

_audit_creation_date             2021-01-15T09:49:41-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_moiety         'C23 H32 O2 P2'
_chemical_formula_sum            'C23 H32 O2 P2'
_chemical_formula_weight         402.42

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   10.1084(14)
_cell_length_b                   20.209(3)
_cell_length_c                   11.8485(17)
_cell_angle_alpha                90
_cell_angle_beta                 110.326(10)
_cell_angle_gamma                90
_cell_volume                     2269.7(6)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    7314
_cell_measurement_theta_min      2.29
_cell_measurement_theta_max      26.67
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.12
_exptl_crystal_density_diffrn    1.178
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             864

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.206
_exptl_absorpt_correction_type   none
_shelx_estimated_absorpt_T_min   0.97
_shelx_estimated_absorpt_T_max   0.976

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_probe          x-ray
_diffrn_standards_number         0
_diffrn_measurement_device       '2-circle diffractometer'
_diffrn_measurement_device_type  'STOE IPDS 2T'
_diffrn_detector                 'image plate (34 cm diameter)'
_diffrn_detector_type            'STOE Imaging Plate'
_diffrn_detector_area_resol_mean 6.67
_diffrn_source                   'GeniX Mo, 0.05 x 0.05 mm2 microfocus'
_diffrn_source_type              ?
_diffrn_source_target            ?
_diffrn_source_voltage           50
_diffrn_source_current           1.000
_diffrn_source_power             0.050
_diffrn_radiation_monochromator  'parabolic x-ray mirror'
_diffrn_radiation_polarisn_norm  270
_diffrn_radiation_collimation    '0.6 mm diameter'
_diffrn_measurement_method       'rotation method, ω scans'
_diffrn_measurement_details      
; 142 frames, detector distance = 100 mm
;
_diffrn_reflns_av_R_equivalents  0.0803
_diffrn_reflns_av_unetI/netI     0.1006
_diffrn_reflns_number            12916
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.289
_diffrn_reflns_theta_max         27.998
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.983
_diffrn_measured_fraction_theta_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_point_group_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.987
_reflns_Friedel_coverage         0
_reflns_number_total             5417
_reflns_number_gt                2744
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       
;
X-Area WinXpose 2.0.22.0 (STOE, 2016)
;
_computing_cell_refinement       
;
X-Area Recipe 1.33.0.0 (STOE, 2015)
;
_computing_data_reduction        
;
X-Area Integrate 1.72.0.0 (STOE, 2018)
X-Area X-Red32 1.63.4.0 (STOE, 2017) 
;
_computing_structure_refinement  'SHELXL-2018/1 (Sheldrick, 2018)'
_computing_molecular_graphics    'Ortep for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1153P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         5417
_refine_ls_number_parameters     252
_refine_ls_number_restraints     0
_refine_ls_number_constraints    0
_refine_ls_R_factor_all          0.1332
_refine_ls_R_factor_gt           0.0707
_refine_ls_wR_factor_ref         0.2019
_refine_ls_wR_factor_gt          0.1759
_refine_ls_goodness_of_fit_ref   0.922
_refine_ls_restrained_S_all      0.922
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.497
_refine_diff_density_min         -0.588
_refine_diff_density_rms         0.076

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 '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'

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
C1 C 0.7768(3) 0.65022(16) 0.4458(3) 0.0433(7) Uani 1 1 d . . . . .
C2 C 0.8547(3) 0.61767(16) 0.3756(3) 0.0443(7) Uani 1 1 d . . . . .
C3 C 0.8755(3) 0.54948(16) 0.3772(3) 0.0464(8) Uani 1 1 d . . . . .
H3 H 0.844829 0.522593 0.429119 0.056 Uiso 1 1 calc R U . . .
C4 C 0.9402(4) 0.52028(18) 0.3039(3) 0.0520(8) Uani 1 1 d . . . . .
H4 H 0.953554 0.473699 0.306339 0.062 Uiso 1 1 calc R U . . .
C5 C 0.9855(3) 0.55841(17) 0.2275(3) 0.0483(8) Uani 1 1 d . . . . .
C6 C 0.9681(3) 0.62621(17) 0.2257(3) 0.0472(8) Uani 1 1 d . . . . .
H6 H 0.999538 0.65288 0.173963 0.057 Uiso 1 1 calc R U . . .
C7 C 0.9047(3) 0.65497(16) 0.2997(3) 0.0445(7) Uani 1 1 d . . . . .
H7 H 0.894843 0.701735 0.298969 0.053 Uiso 1 1 calc R U . . .
C8 C 1.1083(4) 0.56340(19) 0.0882(3) 0.0581(9) Uani 1 1 d . . . . .
H8A H 1.034164 0.589996 0.03063 0.087 Uiso 1 1 calc R U . . .
H8B H 1.150507 0.533914 0.044368 0.087 Uiso 1 1 calc R U . . .
H8C H 1.181118 0.592726 0.140509 0.087 Uiso 1 1 calc R U . . .
C9 C 0.8124(3) 0.72052(16) 0.4785(3) 0.0435(7) Uani 1 1 d . . . . .
C10 C 0.9406(3) 0.73777(16) 0.5653(3) 0.0450(7) Uani 1 1 d . . . . .
H10 H 1.002293 0.703714 0.608512 0.054 Uiso 1 1 calc R U . . .
C11 C 0.9811(3) 0.80332(16) 0.5908(3) 0.0445(7) Uani 1 1 d . . . . .
H11 H 1.068231 0.813753 0.652007 0.053 Uiso 1 1 calc R U . . .
C12 C 0.8934(3) 0.85356(17) 0.5263(3) 0.0451(7) Uani 1 1 d . . . . .
C13 C 0.7639(3) 0.83735(16) 0.4396(3) 0.0468(8) Uani 1 1 d . . . . .
H13 H 0.702688 0.871455 0.395967 0.056 Uiso 1 1 calc R U . . .
C14 C 0.7242(3) 0.77204(16) 0.4168(3) 0.0457(8) Uani 1 1 d . . . . .
H14 H 0.635245 0.761765 0.357965 0.055 Uiso 1 1 calc R U . . .
C15 C 1.0600(4) 0.93763(18) 0.6246(3) 0.0546(9) Uani 1 1 d . . . . .
H15A H 1.067014 0.922772 0.705211 0.082 Uiso 1 1 calc R U . . .
H15B H 1.070118 0.985857 0.624524 0.082 Uiso 1 1 calc R U . . .
H15C H 1.134853 0.916921 0.602035 0.082 Uiso 1 1 calc R U . . .
C16 C 0.3759(4) 0.65982(17) 0.5047(3) 0.0478(8) Uani 1 1 d . . . . .
C17 C 0.3509(4) 0.67488(19) 0.3720(3) 0.0582(9) Uani 1 1 d . . . . .
H17A H 0.249419 0.679301 0.327967 0.087 Uiso 1 1 calc R U . . .
H17B H 0.388722 0.638691 0.337225 0.087 Uiso 1 1 calc R U . . .
H17C H 0.398516 0.716278 0.366011 0.087 Uiso 1 1 calc R U . . .
C18 C 0.3011(4) 0.71407(19) 0.5514(3) 0.0598(9) Uani 1 1 d . . . . .
H18A H 0.200581 0.714634 0.502429 0.09 Uiso 1 1 calc R U . . .
H18B H 0.34296 0.757182 0.546077 0.09 Uiso 1 1 calc R U . . .
H18C H 0.312288 0.704913 0.635441 0.09 Uiso 1 1 calc R U . . .
C19 C 0.3109(4) 0.59346(18) 0.5138(3) 0.0569(9) Uani 1 1 d . . . . .
H19A H 0.318139 0.585631 0.597413 0.085 Uiso 1 1 calc R U . . .
H19B H 0.360997 0.558404 0.488004 0.085 Uiso 1 1 calc R U . . .
H19C H 0.211305 0.593406 0.462012 0.085 Uiso 1 1 calc R U . . .
C20 C 0.6336(4) 0.62208(17) 0.7315(3) 0.0498(8) Uani 1 1 d . . . . .
C21 C 0.6145(4) 0.54699(18) 0.7227(3) 0.0606(10) Uani 1 1 d . . . . .
H21A H 0.666301 0.528715 0.673661 0.091 Uiso 1 1 calc R U . . .
H21B H 0.513998 0.536448 0.685297 0.091 Uiso 1 1 calc R U . . .
H21C H 0.650808 0.52767 0.803554 0.091 Uiso 1 1 calc R U . . .
C22 C 0.7915(4) 0.6366(2) 0.7867(3) 0.0634(10) Uani 1 1 d . . . . .
H22A H 0.828814 0.617649 0.867825 0.095 Uiso 1 1 calc R U . . .
H22B H 0.806699 0.684568 0.791249 0.095 Uiso 1 1 calc R U . . .
H22C H 0.840364 0.616878 0.736504 0.095 Uiso 1 1 calc R U . . .
C23 C 0.5590(4) 0.6512(2) 0.8142(3) 0.0670(11) Uani 1 1 d . . . . .
H23A H 0.606002 0.635276 0.89664 0.101 Uiso 1 1 calc R U . . .
H23B H 0.460101 0.637075 0.78551 0.101 Uiso 1 1 calc R U . . .
H23C H 0.563677 0.699583 0.812918 0.101 Uiso 1 1 calc R U . . .
O1 O 1.0488(2) 0.52494(12) 0.1595(2) 0.0544(6) Uani 1 1 d . . . . .
O2 O 0.9255(2) 0.91916(11) 0.5399(2) 0.0490(6) Uani 1 1 d . . . . .
P1 P 0.65053(9) 0.60456(4) 0.47534(8) 0.0467(3) Uani 1 1 d . . . . .
P2 P 0.57294(9) 0.67152(4) 0.58627(8) 0.0441(2) Uani 1 1 d . . . . .



#----------------------------------------------------------------------------#
#                   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
C1 C2 1.483(4) . ?
C1 C9 1.484(4) . ?
C1 P1 1.707(3) . ?
C2 C3 1.393(4) . ?
C2 C7 1.396(4) . ?
C3 C4 1.387(4) . ?
C3 H3 0.95 . ?
C4 C5 1.383(5) . ?
C4 H4 0.95 . ?
C5 O1 1.369(4) . ?
C5 C6 1.381(5) . ?
C6 C7 1.381(4) . ?
C6 H6 0.95 . ?
C7 H7 0.95 . ?
C8 O1 1.426(4) . ?
C8 H8A 0.98 . ?
C8 H8B 0.98 . ?
C8 H8C 0.98 . ?
C9 C10 1.390(4) . ?
C9 C14 1.400(4) . ?
C10 C11 1.388(4) . ?
C10 H10 0.95 . ?
C11 C12 1.389(4) . ?
C11 H11 0.95 . ?
C12 O2 1.361(4) . ?
C12 C13 1.394(4) . ?
C13 C14 1.379(4) . ?
C13 H13 0.95 . ?
C14 H14 0.95 . ?
C15 O2 1.430(4) . ?
C15 H15A 0.98 . ?
C15 H15B 0.98 . ?
C15 H15C 0.98 . ?
C16 C19 1.514(4) . ?
C16 C17 1.534(5) . ?
C16 C18 1.539(5) . ?
C16 P2 1.902(3) . ?
C17 H17A 0.98 . ?
C17 H17B 0.98 . ?
C17 H17C 0.98 . ?
C18 H18A 0.98 . ?
C18 H18B 0.98 . ?
C18 H18C 0.98 . ?
C19 H19A 0.98 . ?
C19 H19B 0.98 . ?
C19 H19C 0.98 . ?
C20 C21 1.529(5) . ?
C20 C22 1.529(5) . ?
C20 C23 1.545(5) . ?
C20 P2 1.898(3) . ?
C21 H21A 0.98 . ?
C21 H21B 0.98 . ?
C21 H21C 0.98 . ?
C22 H22A 0.98 . ?
C22 H22B 0.98 . ?
C22 H22C 0.98 . ?
C23 H23A 0.98 . ?
C23 H23B 0.98 . ?
C23 H23C 0.98 . ?
P1 P2 2.2114(12) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C9 116.3(3) . . ?
C2 C1 P1 117.1(2) . . ?
C9 C1 P1 126.5(2) . . ?
C3 C2 C7 117.1(3) . . ?
C3 C2 C1 122.6(3) . . ?
C7 C2 C1 120.2(3) . . ?
C4 C3 C2 120.9(3) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
C5 C4 C3 120.5(3) . . ?
C5 C4 H4 119.7 . . ?
C3 C4 H4 119.7 . . ?
O1 C5 C6 124.3(3) . . ?
O1 C5 C4 116.0(3) . . ?
C6 C5 C4 119.6(3) . . ?
C5 C6 C7 119.5(3) . . ?
C5 C6 H6 120.2 . . ?
C7 C6 H6 120.3 . . ?
C6 C7 C2 122.2(3) . . ?
C6 C7 H7 118.9 . . ?
C2 C7 H7 118.9 . . ?
O1 C8 H8A 109.5 . . ?
O1 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
O1 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C10 C9 C14 117.4(3) . . ?
C10 C9 C1 120.9(3) . . ?
C14 C9 C1 121.5(3) . . ?
C11 C10 C9 121.9(3) . . ?
C11 C10 H10 119 . . ?
C9 C10 H10 119 . . ?
C10 C11 C12 119.6(3) . . ?
C10 C11 H11 120.2 . . ?
C12 C11 H11 120.2 . . ?
O2 C12 C11 124.5(3) . . ?
O2 C12 C13 116.1(3) . . ?
C11 C12 C13 119.3(3) . . ?
C14 C13 C12 120.3(3) . . ?
C14 C13 H13 119.9 . . ?
C12 C13 H13 119.9 . . ?
C13 C14 C9 121.4(3) . . ?
C13 C14 H14 119.3 . . ?
C9 C14 H14 119.3 . . ?
O2 C15 H15A 109.5 . . ?
O2 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
O2 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C19 C16 C17 109.1(3) . . ?
C19 C16 C18 109.0(3) . . ?
C17 C16 C18 107.5(3) . . ?
C19 C16 P2 118.6(2) . . ?
C17 C16 P2 105.5(2) . . ?
C18 C16 P2 106.7(2) . . ?
C16 C17 H17A 109.5 . . ?
C16 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C16 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
C16 C18 H18A 109.5 . . ?
C16 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
C16 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C16 C19 H19A 109.5 . . ?
C16 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
C16 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C21 C20 C22 108.0(3) . . ?
C21 C20 C23 110.0(3) . . ?
C22 C20 C23 108.8(3) . . ?
C21 C20 P2 117.9(2) . . ?
C22 C20 P2 104.3(2) . . ?
C23 C20 P2 107.4(2) . . ?
C20 C21 H21A 109.5 . . ?
C20 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
C20 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C20 C22 H22A 109.5 . . ?
C20 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C20 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C20 C23 H23A 109.5 . . ?
C20 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
C20 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C5 O1 C8 117.3(3) . . ?
C12 O2 C15 117.8(3) . . ?
C1 P1 P2 103.65(12) . . ?
C20 P2 C16 110.29(15) . . ?
C20 P2 P1 98.46(11) . . ?
C16 P2 P1 98.44(11) . . ?

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
C9 C1 C2 C3 154.7(3) . . . . ?
P1 C1 C2 C3 -27.9(4) . . . . ?
C9 C1 C2 C7 -28.4(4) . . . . ?
P1 C1 C2 C7 148.9(3) . . . . ?
C7 C2 C3 C4 -1.5(5) . . . . ?
C1 C2 C3 C4 175.4(3) . . . . ?
C2 C3 C4 C5 -0.1(5) . . . . ?
C3 C4 C5 O1 179.7(3) . . . . ?
C3 C4 C5 C6 1.1(5) . . . . ?
O1 C5 C6 C7 -178.9(3) . . . . ?
C4 C5 C6 C7 -0.5(5) . . . . ?
C5 C6 C7 C2 -1.2(5) . . . . ?
C3 C2 C7 C6 2.1(5) . . . . ?
C1 C2 C7 C6 -174.9(3) . . . . ?
C2 C1 C9 C10 -71.7(4) . . . . ?
P1 C1 C9 C10 111.2(3) . . . . ?
C2 C1 C9 C14 102.9(3) . . . . ?
P1 C1 C9 C14 -74.1(4) . . . . ?
C14 C9 C10 C11 0.0(5) . . . . ?
C1 C9 C10 C11 174.8(3) . . . . ?
C9 C10 C11 C12 -1.6(5) . . . . ?
C10 C11 C12 O2 -176.8(3) . . . . ?
C10 C11 C12 C13 2.1(5) . . . . ?
O2 C12 C13 C14 178.0(3) . . . . ?
C11 C12 C13 C14 -1.0(5) . . . . ?
C12 C13 C14 C9 -0.6(5) . . . . ?
C10 C9 C14 C13 1.1(5) . . . . ?
C1 C9 C14 C13 -173.7(3) . . . . ?
C6 C5 O1 C8 4.2(4) . . . . ?
C4 C5 O1 C8 -174.3(3) . . . . ?
C11 C12 O2 C15 1.4(4) . . . . ?
C13 C12 O2 C15 -177.5(3) . . . . ?
C2 C1 P1 P2 177.6(2) . . . . ?
C9 C1 P1 P2 -5.3(3) . . . . ?
C21 C20 P2 C16 60.7(3) . . . . ?
C22 C20 P2 C16 -179.6(2) . . . . ?
C23 C20 P2 C16 -64.2(3) . . . . ?
C21 C20 P2 P1 -41.6(3) . . . . ?
C22 C20 P2 P1 78.1(2) . . . . ?
C23 C20 P2 P1 -166.5(2) . . . . ?



# END of CIF
