# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2024

####################################################################### 
# 
# 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. 
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data_gavr76
_audit_block_doi                 10.5517/ccdc.csd.cc2g8g29
_database_code_depnum_ccdc_archive 'CCDC 2272240'
loop_
_audit_author_name
_audit_author_address
Tafeenko
;MSU
Russia
;
_audit_update_record             
;
2023-06-25 deposited with the CCDC.	2024-07-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H33 N2 O P S'
_chemical_formula_sum            'C22 H33 N2 O P S'
_chemical_formula_weight         404.53

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

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

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

_cell_length_a                   6.8320(4)
_cell_length_b                   19.1764(8)
_cell_length_c                   9.1559(6)
_cell_angle_alpha                90
_cell_angle_beta                 90.016(5)
_cell_angle_gamma                90
_cell_volume                     1199.54(12)
_cell_formula_units_Z            2
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    9314
_cell_measurement_theta_min      4.83
_cell_measurement_theta_max      65.07

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.120
_exptl_crystal_F_000             436
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          .23
_exptl_crystal_size_mid          .14
_exptl_crystal_size_min          .11
_exptl_absorpt_coefficient_mu    1.917
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
[c.f. r.h. blessing, acta cryst. (1995), a51, 33-38]
;

_exptl_absorpt_correction_T_min  0.418
_exptl_absorpt_correction_T_max  0.627

_exptl_special_details           
;
 ?
;

_diffrn_detector                 Pilatus100K
_diffrn_measurement_device_type  'stadivari pilatus100k'
_diffrn_detector_type            STOE
_diffrn_detector_area_resol_mean 5.81
_diffrn_source                   'Cu GeniX 3D'
_diffrn_source_voltage           50
_diffrn_source_current           0.600
_diffrn_source_power             0.030
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54186
_diffrn_radiation_monochromator  none
_diffrn_radiation_polarisn_norm  0
_diffrn_radiation_collimation    'focusing mirrors'
_diffrn_ambient_temperature      295
_diffrn_measurement_method       'rotation method'
_diffrn_reflns_number            10845
_diffrn_reflns_av_unetI/netI     0.0643
_diffrn_reflns_av_R_equivalents  0.0784
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_theta_min         4.612
_diffrn_reflns_theta_max         66.150
_diffrn_reflns_theta_full        66.150
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 0.983
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_Laue_measured_fraction_full 0.983
_diffrn_reflns_point_group_measured_fraction_max 0.892
_diffrn_reflns_point_group_measured_fraction_full 0.892
_reflns_number_total             3738
_reflns_number_gt                2514
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.871
_reflns_Friedel_fraction_max     0.859
_reflns_Friedel_fraction_full    0.859

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1049P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 936 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.09(4)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         3738
_refine_ls_number_parameters     247
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0844
_refine_ls_R_factor_gt           0.0598
_refine_ls_wR_factor_ref         0.1639
_refine_ls_wR_factor_gt          0.1495
_refine_ls_goodness_of_fit_ref   0.943
_refine_ls_restrained_S_all      0.943
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.2466(2) 0.27868(9) -0.11184(16) 0.0653(5) Uani 1 1 d . . . . .
S1 S -0.0648(4) 0.39000(12) 0.2469(3) 0.1090(8) Uani 1 1 d . . . . .
O1 O 0.1734(6) 0.2494(3) 0.0465(4) 0.0682(12) Uani 1 1 d . . . . .
N1 N 0.4841(8) 0.2482(3) -0.1228(5) 0.0663(14) Uani 1 1 d . . . . .
N2 N 0.3201(8) 0.3661(3) -0.0904(6) 0.0700(15) Uani 1 1 d . . . . .
C3 C 0.6319(11) 0.3048(4) -0.1126(10) 0.084(2) Uani 1 1 d . . . . .
H3A H 0.708981 0.305750 -0.201521 0.101 Uiso 1 1 calc R U . . .
H3B H 0.719776 0.295216 -0.031793 0.101 Uiso 1 1 calc R U . . .
C4 C 0.5323(11) 0.3791(4) -0.0888(9) 0.082(2) Uani 1 1 d . . . . .
H4 H 0.570248 0.397501 0.006961 0.098 Uiso 1 1 calc R U . . .
C5 C 0.561(2) 0.4364(7) -0.206(2) 0.184(7) Uani 1 1 d . . . . .
H5A H 0.648355 0.471825 -0.167513 0.221 Uiso 1 1 calc R U . . .
H5B H 0.621796 0.416054 -0.291156 0.221 Uiso 1 1 calc R U . . .
C6 C 0.3815(19) 0.4683(7) -0.2472(16) 0.156(5) Uani 1 1 d . . . . .
H6A H 0.361745 0.464594 -0.351877 0.187 Uiso 1 1 calc R U . . .
H6B H 0.380494 0.517194 -0.220166 0.187 Uiso 1 1 calc R U . . .
C7 C 0.2234(14) 0.4285(4) -0.1651(10) 0.098(3) Uani 1 1 d . . . . .
H7A H 0.123143 0.412725 -0.232421 0.117 Uiso 1 1 calc R U . . .
H7B H 0.162663 0.458537 -0.092862 0.117 Uiso 1 1 calc R U . . .
C8 C 0.5360(10) 0.1743(3) -0.1451(6) 0.0621(16) Uani 1 1 d . . . . .
C9 C 0.7312(11) 0.1526(4) -0.1531(9) 0.088(2) Uani 1 1 d . . . . .
H9 H 0.831408 0.185169 -0.144379 0.105 Uiso 1 1 calc R U . . .
C10 C 0.7786(15) 0.0789(5) -0.1750(11) 0.106(3) Uani 1 1 d . . . . .
H10 H 0.909982 0.066275 -0.177942 0.127 Uiso 1 1 calc R U . . .
C11 C 0.6406(18) 0.0269(5) -0.1917(11) 0.109(3) Uani 1 1 d . . . . .
H11 H 0.676421 -0.019222 -0.207624 0.131 Uiso 1 1 calc R U . . .
C12 C 0.4446(16) 0.0470(4) -0.1834(10) 0.099(3) Uani 1 1 d . . . . .
H12 H 0.346361 0.013802 -0.193151 0.119 Uiso 1 1 calc R U . . .
C13 C 0.3931(12) 0.1201(4) -0.1595(8) 0.079(2) Uani 1 1 d . . . . .
H13 H 0.261338 0.131970 -0.153352 0.095 Uiso 1 1 calc R U . . .
C14 C 0.2810(9) 0.2608(4) 0.1819(6) 0.0676(18) Uani 1 1 d . . . . .
H14 H 0.354720 0.304665 0.179221 0.081 Uiso 1 1 calc R U . . .
C15 C 0.1378(9) 0.2586(3) 0.3143(6) 0.0629(16) Uani 1 1 d . . . . .
C16 C 0.2578(11) 0.2917(4) 0.4399(8) 0.084(2) Uani 1 1 d . . . . .
H16A H 0.175492 0.302279 0.523364 0.100 Uiso 1 1 calc R U . . .
H16B H 0.323340 0.333929 0.408166 0.100 Uiso 1 1 calc R U . . .
C17 C 0.4107(13) 0.2317(5) 0.4769(8) 0.103(3) Uani 1 1 d . . . . .
H17A H 0.543712 0.247799 0.461662 0.123 Uiso 1 1 calc R U . . .
H17B H 0.396921 0.216578 0.577474 0.123 Uiso 1 1 calc R U . . .
C18 C 0.3593(11) 0.1702(5) 0.3679(8) 0.092(2) Uani 1 1 d . . . . .
H18 H 0.410278 0.124409 0.396340 0.110 Uiso 1 1 calc R U . . .
C19 C 0.4222(11) 0.1952(5) 0.2149(8) 0.089(2) Uani 1 1 d . . . . .
H19A H 0.403590 0.158758 0.142806 0.107 Uiso 1 1 calc R U . . .
H19B H 0.558587 0.209305 0.214589 0.107 Uiso 1 1 calc R U . . .
C20 C 0.1323(11) 0.1748(4) 0.3575(7) 0.0742(18) Uani 1 1 d . . . . .
C21 C 0.0435(14) 0.1230(4) 0.2412(10) 0.101(3) Uani 1 1 d . . . . .
H21A H 0.109289 0.129181 0.149497 0.152 Uiso 1 1 calc R U . . .
H21B H -0.093511 0.132497 0.229257 0.152 Uiso 1 1 calc R U . . .
H21C H 0.060746 0.075901 0.274192 0.152 Uiso 1 1 calc R U . . .
C22 C 0.0312(13) 0.1595(5) 0.5036(9) 0.100(3) Uani 1 1 d . . . . .
H22A H 0.049430 0.111360 0.528659 0.150 Uiso 1 1 calc R U . . .
H22B H -0.106203 0.169262 0.495117 0.150 Uiso 1 1 calc R U . . .
H22C H 0.086971 0.188437 0.578381 0.150 Uiso 1 1 calc R U . . .
C23 C -0.0599(10) 0.2925(4) 0.2868(8) 0.080(2) Uani 1 1 d . . . . .
H23A H -0.141349 0.284070 0.371772 0.096 Uiso 1 1 calc R U . . .
H23B H -0.120665 0.268645 0.205070 0.096 Uiso 1 1 calc R U . . .
C24 C -0.097(2) 0.4282(7) 0.4212(14) 0.169(6) Uani 1 1 d . . . . .
H24A H -0.203961 0.406081 0.470356 0.253 Uiso 1 1 calc R U . . .
H24B H -0.123674 0.477072 0.410208 0.253 Uiso 1 1 calc R U . . .
H24C H 0.020741 0.422284 0.477592 0.253 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 O1 1.633(4) . ?
P1 N1 1.727(6) . ?
P1 N2 1.761(6) . ?
S1 C24 1.770(12) . ?
S1 C23 1.906(8) . ?
O1 C14 1.458(7) . ?
N1 C8 1.475(8) . ?
N1 C3 1.486(8) . ?
N2 C4 1.471(9) . ?
N2 C7 1.528(9) . ?
C3 C4 1.594(11) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.545(13) . ?
C4 H4 0.9800 . ?
C5 C6 1.421(16) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C7 1.521(14) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.399(10) . ?
C8 C13 1.432(10) . ?
C9 C10 1.464(12) . ?
C9 H9 0.9300 . ?
C10 C11 1.380(13) . ?
C10 H10 0.9300 . ?
C11 C12 1.395(13) . ?
C11 H11 0.9300 . ?
C12 C13 1.461(11) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 C15 1.558(8) . ?
C14 C19 1.613(10) . ?
C14 H14 0.9800 . ?
C15 C23 1.520(9) . ?
C15 C16 1.549(9) . ?
C15 C20 1.655(10) . ?
C16 C17 1.591(12) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C18 1.584(13) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 C19 1.543(10) . ?
C18 C20 1.556(10) . ?
C18 H18 0.9800 . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 C22 1.534(10) . ?
C20 C21 1.576(11) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C24 H24A 0.9600 . ?
C24 H24B 0.9600 . ?
C24 H24C 0.9600 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 P1 N1 102.9(2) . . ?
O1 P1 N2 108.4(3) . . ?
N1 P1 N2 93.5(3) . . ?
C24 S1 C23 103.6(5) . . ?
C14 O1 P1 123.3(4) . . ?
C8 N1 C3 123.2(5) . . ?
C8 N1 P1 124.0(4) . . ?
C3 N1 P1 112.8(4) . . ?
C4 N2 C7 107.3(6) . . ?
C4 N2 P1 116.3(4) . . ?
C7 N2 P1 125.0(5) . . ?
N1 C3 C4 111.8(6) . . ?
N1 C3 H3A 109.3 . . ?
C4 C3 H3A 109.3 . . ?
N1 C3 H3B 109.3 . . ?
C4 C3 H3B 109.3 . . ?
H3A C3 H3B 107.9 . . ?
N2 C4 C5 103.8(8) . . ?
N2 C4 C3 105.5(6) . . ?
C5 C4 C3 119.2(9) . . ?
N2 C4 H4 109.3 . . ?
C5 C4 H4 109.3 . . ?
C3 C4 H4 109.3 . . ?
C6 C5 C4 112.5(9) . . ?
C6 C5 H5A 109.1 . . ?
C4 C5 H5A 109.1 . . ?
C6 C5 H5B 109.1 . . ?
C4 C5 H5B 109.1 . . ?
H5A C5 H5B 107.8 . . ?
C5 C6 C7 105.3(8) . . ?
C5 C6 H6A 110.7 . . ?
C7 C6 H6A 110.7 . . ?
C5 C6 H6B 110.7 . . ?
C7 C6 H6B 110.7 . . ?
H6A C6 H6B 108.8 . . ?
C6 C7 N2 107.9(8) . . ?
C6 C7 H7A 110.1 . . ?
N2 C7 H7A 110.1 . . ?
C6 C7 H7B 110.1 . . ?
N2 C7 H7B 110.1 . . ?
H7A C7 H7B 108.4 . . ?
C9 C8 C13 115.4(6) . . ?
C9 C8 N1 121.5(6) . . ?
C13 C8 N1 123.1(6) . . ?
C8 C9 C10 120.3(7) . . ?
C8 C9 H9 119.8 . . ?
C10 C9 H9 119.8 . . ?
C11 C10 C9 124.1(9) . . ?
C11 C10 H10 117.9 . . ?
C9 C10 H10 117.9 . . ?
C10 C11 C12 116.7(9) . . ?
C10 C11 H11 121.6 . . ?
C12 C11 H11 121.6 . . ?
C11 C12 C13 120.3(8) . . ?
C11 C12 H12 119.9 . . ?
C13 C12 H12 119.9 . . ?
C8 C13 C12 123.0(7) . . ?
C8 C13 H13 118.5 . . ?
C12 C13 H13 118.5 . . ?
O1 C14 C15 109.9(5) . . ?
O1 C14 C19 110.1(5) . . ?
C15 C14 C19 102.0(5) . . ?
O1 C14 H14 111.5 . . ?
C15 C14 H14 111.5 . . ?
C19 C14 H14 111.5 . . ?
C23 C15 C16 114.7(6) . . ?
C23 C15 C14 114.7(5) . . ?
C16 C15 C14 103.5(5) . . ?
C23 C15 C20 115.8(5) . . ?
C16 C15 C20 103.5(5) . . ?
C14 C15 C20 103.1(5) . . ?
C15 C16 C17 102.0(6) . . ?
C15 C16 H16A 111.4 . . ?
C17 C16 H16A 111.4 . . ?
C15 C16 H16B 111.4 . . ?
C17 C16 H16B 111.4 . . ?
H16A C16 H16B 109.2 . . ?
C18 C17 C16 105.0(6) . . ?
C18 C17 H17A 110.7 . . ?
C16 C17 H17A 110.7 . . ?
C18 C17 H17B 110.7 . . ?
C16 C17 H17B 110.7 . . ?
H17A C17 H17B 108.8 . . ?
C19 C18 C20 101.8(5) . . ?
C19 C18 C17 106.2(7) . . ?
C20 C18 C17 102.6(6) . . ?
C19 C18 H18 114.9 . . ?
C20 C18 H18 114.9 . . ?
C17 C18 H18 114.9 . . ?
C18 C19 C14 104.2(6) . . ?
C18 C19 H19A 110.9 . . ?
C14 C19 H19A 110.9 . . ?
C18 C19 H19B 110.9 . . ?
C14 C19 H19B 110.9 . . ?
H19A C19 H19B 108.9 . . ?
C22 C20 C18 112.6(6) . . ?
C22 C20 C21 107.2(6) . . ?
C18 C20 C21 112.9(6) . . ?
C22 C20 C15 113.8(6) . . ?
C18 C20 C15 92.7(5) . . ?
C21 C20 C15 117.3(6) . . ?
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 . . ?
C15 C23 S1 117.8(5) . . ?
C15 C23 H23A 107.8 . . ?
S1 C23 H23A 107.8 . . ?
C15 C23 H23B 107.8 . . ?
S1 C23 H23B 107.8 . . ?
H23A C23 H23B 107.2 . . ?
S1 C24 H24A 109.5 . . ?
S1 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
S1 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 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
N1 P1 O1 C14 52.5(5) . . . . ?
N2 P1 O1 C14 -45.7(5) . . . . ?
O1 P1 N1 C8 71.4(5) . . . . ?
N2 P1 N1 C8 -178.8(4) . . . . ?
O1 P1 N1 C3 -110.7(5) . . . . ?
N2 P1 N1 C3 -0.9(5) . . . . ?
O1 P1 N2 C4 104.4(5) . . . . ?
N1 P1 N2 C4 -0.4(5) . . . . ?
O1 P1 N2 C7 -117.0(6) . . . . ?
N1 P1 N2 C7 138.2(6) . . . . ?
C8 N1 C3 C4 179.8(6) . . . . ?
P1 N1 C3 C4 1.9(8) . . . . ?
C7 N2 C4 C5 -17.9(10) . . . . ?
P1 N2 C4 C5 127.5(9) . . . . ?
C7 N2 C4 C3 -144.0(6) . . . . ?
P1 N2 C4 C3 1.5(7) . . . . ?
N1 C3 C4 N2 -2.0(8) . . . . ?
N1 C3 C4 C5 -118.0(10) . . . . ?
N2 C4 C5 C6 14.1(17) . . . . ?
C3 C4 C5 C6 131.0(13) . . . . ?
C4 C5 C6 C7 -4.0(19) . . . . ?
C5 C6 C7 N2 -7.5(16) . . . . ?
C4 N2 C7 C6 16.5(10) . . . . ?
P1 N2 C7 C6 -125.1(9) . . . . ?
C3 N1 C8 C9 2.3(9) . . . . ?
P1 N1 C8 C9 -180.0(5) . . . . ?
C3 N1 C8 C13 -178.0(7) . . . . ?
P1 N1 C8 C13 -0.2(8) . . . . ?
C13 C8 C9 C10 0.1(10) . . . . ?
N1 C8 C9 C10 179.9(7) . . . . ?
C8 C9 C10 C11 1.2(14) . . . . ?
C9 C10 C11 C12 -1.5(15) . . . . ?
C10 C11 C12 C13 0.5(14) . . . . ?
C9 C8 C13 C12 -1.0(10) . . . . ?
N1 C8 C13 C12 179.2(7) . . . . ?
C11 C12 C13 C8 0.7(13) . . . . ?
P1 O1 C14 C15 153.9(4) . . . . ?
P1 O1 C14 C19 -94.5(6) . . . . ?
O1 C14 C15 C23 -38.7(7) . . . . ?
C19 C14 C15 C23 -155.5(6) . . . . ?
O1 C14 C15 C16 -164.4(5) . . . . ?
C19 C14 C15 C16 78.9(6) . . . . ?
O1 C14 C15 C20 88.0(6) . . . . ?
C19 C14 C15 C20 -28.7(6) . . . . ?
C23 C15 C16 C17 161.2(6) . . . . ?
C14 C15 C16 C17 -73.2(6) . . . . ?
C20 C15 C16 C17 34.2(6) . . . . ?
C15 C16 C17 C18 -0.4(8) . . . . ?
C16 C17 C18 C19 70.6(7) . . . . ?
C16 C17 C18 C20 -35.8(7) . . . . ?
C20 C18 C19 C14 42.4(7) . . . . ?
C17 C18 C19 C14 -64.7(7) . . . . ?
O1 C14 C19 C18 -123.4(6) . . . . ?
C15 C14 C19 C18 -6.7(7) . . . . ?
C19 C18 C20 C22 -174.0(7) . . . . ?
C17 C18 C20 C22 -64.2(8) . . . . ?
C19 C18 C20 C21 64.4(8) . . . . ?
C17 C18 C20 C21 174.2(6) . . . . ?
C19 C18 C20 C15 -56.8(6) . . . . ?
C17 C18 C20 C15 53.0(6) . . . . ?
C23 C15 C20 C22 -64.9(8) . . . . ?
C16 C15 C20 C22 61.5(7) . . . . ?
C14 C15 C20 C22 169.1(6) . . . . ?
C23 C15 C20 C18 178.9(5) . . . . ?
C16 C15 C20 C18 -54.8(6) . . . . ?
C14 C15 C20 C18 52.9(5) . . . . ?
C23 C15 C20 C21 61.4(8) . . . . ?
C16 C15 C20 C21 -172.3(6) . . . . ?
C14 C15 C20 C21 -64.7(7) . . . . ?
C16 C15 C23 S1 56.3(7) . . . . ?
C14 C15 C23 S1 -63.3(7) . . . . ?
C20 C15 C23 S1 176.7(4) . . . . ?

_refine_diff_density_max         0.227
_refine_diff_density_min         -0.270
_refine_diff_density_rms         0.049

####################################################################### 
# 
# 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_gavr77
_audit_block_doi                 10.5517/ccdc.csd.cc2g8g3b
_database_code_depnum_ccdc_archive 'CCDC 2272241'
loop_
_audit_author_name
_audit_author_address
Tafeenko
;MSU
Russia
;
_audit_update_record             
;
2023-06-25 deposited with the CCDC.	2024-07-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C27 H35 N2 O P S'
_chemical_formula_sum            'C27 H35 N2 O P S'
_chemical_formula_weight         466.60

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

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

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

_cell_length_a                   5.9569(5)
_cell_length_b                   18.7798(7)
_cell_length_c                   11.6407(6)
_cell_angle_alpha                90
_cell_angle_beta                 100.637(6)
_cell_angle_gamma                90
_cell_volume                     1279.86(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    15296
_cell_measurement_theta_min      2.85
_cell_measurement_theta_max      19.01

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.211
_exptl_crystal_F_000             500
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          .19
_exptl_crystal_size_mid          .14
_exptl_crystal_size_min          .11
_exptl_absorpt_coefficient_mu    0.210
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
[c.f. r.h. blessing, acta cryst. (1995), a51, 33-38]
;

_exptl_absorpt_correction_T_min  0.405
_exptl_absorpt_correction_T_max  0.602
_diffrn_measurement_device_type  STOE
_diffrn_detector                 Pilatus100K
_diffrn_detector_type            STOE
_diffrn_detector_area_resol_mean 5.81
_diffrn_source                   'Mo LFF Sealed Tube'
_diffrn_source_voltage           50
_diffrn_source_current           40
_diffrn_source_power             2.000
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_radiation_polarisn_norm  0
_diffrn_radiation_collimation    '0.5 mm diameter, monocapillary'
_diffrn_ambient_temperature      295
_diffrn_measurement_method       'rotation method'
_diffrn_reflns_number            28353
_diffrn_reflns_av_unetI/netI     0.2828
_diffrn_reflns_av_R_equivalents  0.1493
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.806
_diffrn_reflns_theta_max         28.731
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measured_fraction_theta_full 0.989
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_Laue_measured_fraction_full 0.989
_diffrn_reflns_point_group_measured_fraction_max 0.876
_diffrn_reflns_point_group_measured_fraction_full 0.989
_reflns_number_total             5795
_reflns_number_gt                1532
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.856
_reflns_Friedel_fraction_max     0.832
_reflns_Friedel_fraction_full    0.901

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0145P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    refall
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Classical Flack method preferred over Parsons because s.u. lower.
;
_refine_ls_abs_structure_Flack   -0.05(15)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         5795
_refine_ls_number_parameters     295
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.2467
_refine_ls_R_factor_gt           0.0537
_refine_ls_wR_factor_ref         0.1082
_refine_ls_wR_factor_gt          0.0868
_refine_ls_goodness_of_fit_ref   0.875
_refine_ls_restrained_S_all      0.874
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 0.3459(4) 0.56927(10) 0.4632(2) 0.0758(7) Uani 1 1 d . . . . .
S1 S 0.8606(5) 0.28965(11) 0.4133(3) 0.1183(10) Uani 1 1 d . . . . .
O1 O 0.3786(8) 0.4930(2) 0.3985(4) 0.0744(16) Uani 1 1 d . . . . .
N1 N 0.5274(12) 0.6247(3) 0.4074(9) 0.0729(19) Uani 1 1 d . . . . .
N2 N 0.5216(13) 0.5678(4) 0.5906(6) 0.0732(17) Uani 1 1 d . . . . .
C3 C 0.7314(16) 0.6447(4) 0.4875(10) 0.095(3) Uani 1 1 d . . . . .
H3A H 0.724560 0.694617 0.508289 0.114 Uiso 1 1 calc R U . . .
H3B H 0.864460 0.637505 0.451871 0.114 Uiso 1 1 calc R U . . .
C4 C 0.7469(16) 0.5986(5) 0.5953(9) 0.093(3) Uani 1 1 d . . . . .
H4 H 0.847(8) 0.563(3) 0.5912(10) 0.111 Uiso 1 1 calc R U . . .
C5 C 0.807(2) 0.6334(6) 0.7144(11) 0.149(4) Uani 1 1 d . . . . .
H5A H 0.925014 0.606409 0.764718 0.179 Uiso 1 1 calc R U . . .
H5B H 0.861931 0.681534 0.707312 0.179 Uiso 1 1 calc R U . . .
C6 C 0.605(2) 0.6339(7) 0.7599(11) 0.171(5) Uani 1 1 d . . . . .
H6A H 0.533686 0.680387 0.748284 0.205 Uiso 1 1 calc R U . . .
H6B H 0.639490 0.624237 0.843134 0.205 Uiso 1 1 calc R U . . .
C7 C 0.4508(15) 0.5800(6) 0.7011(9) 0.117(3) Uani 1 1 d . . . . .
H7A H 0.462672 0.536494 0.746838 0.140 Uiso 1 1 calc R U . . .
H7B H 0.294054 0.596606 0.688962 0.140 Uiso 1 1 calc R U . . .
C8 C 0.487(2) 0.6494(4) 0.2915(12) 0.074(2) Uani 1 1 d . . . . .
C9 C 0.290(2) 0.6330(4) 0.2169(14) 0.089(3) Uani 1 1 d . . . . .
H9 H 0.181329 0.605916 0.245354 0.107 Uiso 1 1 calc R U . . .
C10 C 0.242(2) 0.6539(6) 0.1028(14) 0.118(4) Uani 1 1 d . . . . .
H10 H 0.106188 0.640819 0.054583 0.141 Uiso 1 1 calc R U . . .
C11 C 0.400(3) 0.6949(6) 0.0611(11) 0.120(4) Uani 1 1 d . . . . .
H11 H 0.371815 0.710280 -0.016131 0.144 Uiso 1 1 calc R U . . .
C12 C 0.600(3) 0.7130(5) 0.1334(16) 0.121(5) Uani 1 1 d . . . . .
H12 H 0.707324 0.739791 0.103605 0.145 Uiso 1 1 calc R U . . .
C13 C 0.6457(17) 0.6929(5) 0.2484(12) 0.094(3) Uani 1 1 d . . . . .
H13 H 0.779030 0.707769 0.297268 0.113 Uiso 1 1 calc R U . . .
C14 C 0.5764(13) 0.4036(4) 0.3122(8) 0.074(3) Uani 1 1 d . . . . .
H14 H 0.489(6) 0.372(2) 0.339(2) 0.089 Uiso 1 1 calc R U . . .
C15 C 0.8095(12) 0.3663(4) 0.3130(8) 0.081(2) Uani 1 1 d . . . . .
H15 H 0.927979 0.401512 0.341952 0.097 Uiso 1 1 calc R U . . .
C16 C 0.8572(14) 0.3401(4) 0.1953(9) 0.092(3) Uani 1 1 d . . . . .
H16A H 1.007453 0.356222 0.185974 0.111 Uiso 1 1 calc R U . . .
H16B H 0.857796 0.288470 0.194914 0.111 Uiso 1 1 calc R U . . .
C17 C 0.6834(14) 0.3664(4) 0.0943(8) 0.075(2) Uani 1 1 d . . . . .
H17 H 0.712(2) 0.3522(10) 0.015(5) 0.090 Uiso 1 1 calc R U . . .
C18 C 0.4426(12) 0.3501(4) 0.1173(7) 0.084(2) Uani 1 1 d . . . . .
H18A H 0.433746 0.307766 0.163978 0.101 Uiso 1 1 calc R U . . .
H18B H 0.324739 0.350151 0.047589 0.101 Uiso 1 1 calc R U . . .
C19 C 0.4604(13) 0.4207(4) 0.1877(8) 0.067(2) Uani 1 1 d . . . . .
H19 H 0.309(9) 0.4490(17) 0.1805(9) 0.080 Uiso 1 1 calc R U . . .
C20 C 0.6247(14) 0.4473(4) 0.1080(9) 0.075(2) Uani 1 1 d . . . . .
C21 C 0.8222(12) 0.4982(4) 0.1513(7) 0.101(3) Uani 1 1 d . . . . .
H21A H 0.763533 0.545376 0.157655 0.151 Uiso 1 1 calc R U . . .
H21B H 0.925371 0.498427 0.096952 0.151 Uiso 1 1 calc R U . . .
H21C H 0.901854 0.482816 0.226497 0.151 Uiso 1 1 calc R U . . .
C22 C 0.4853(15) 0.4771(5) -0.0072(7) 0.122(3) Uani 1 1 d . . . . .
H22A H 0.358152 0.446235 -0.034489 0.183 Uiso 1 1 calc R U . . .
H22B H 0.581040 0.479666 -0.065023 0.183 Uiso 1 1 calc R U . . .
H22C H 0.430291 0.523826 0.006252 0.183 Uiso 1 1 calc R U . . .
C23 C 0.5972(12) 0.4667(4) 0.3940(7) 0.072(2) Uani 1 1 d . . . . .
H23A H 0.673144 0.452420 0.471554 0.087 Uiso 1 1 calc R U . . .
H23B H 0.688026 0.503699 0.366478 0.087 Uiso 1 1 calc R U . . .
C24 C 0.898(2) 0.3267(5) 0.5535(9) 0.088(3) Uani 1 1 d . . . . .
C25 C 0.7458(19) 0.3139(5) 0.6256(14) 0.110(3) Uani 1 1 d . . . . .
H25 H 0.619292 0.285455 0.598547 0.132 Uiso 1 1 calc R U . . .
C26 C 0.773(2) 0.3413(8) 0.7355(14) 0.137(4) Uani 1 1 d . . . . .
H26 H 0.670402 0.330172 0.784353 0.164 Uiso 1 1 calc R U . . .
C27 C 0.951(3) 0.3849(7) 0.7716(11) 0.133(4) Uani 1 1 d . . . . .
H27 H 0.969020 0.405404 0.845420 0.160 Uiso 1 1 calc R U . . .
C28 C 1.106(2) 0.3996(6) 0.7025(16) 0.129(4) Uani 1 1 d . . . . .
H28 H 1.229352 0.428984 0.730694 0.155 Uiso 1 1 calc R U . . .
C29 C 1.083(2) 0.3720(7) 0.5916(13) 0.110(3) Uani 1 1 d . . . . .
H29 H 1.186312 0.383083 0.543647 0.132 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 O1 1.646(5) . ?
P1 N2 1.650(6) . ?
P1 N1 1.713(7) . ?
S1 C24 1.749(10) . ?
S1 C15 1.844(7) . ?
O1 C23 1.402(7) . ?
N1 C8 1.404(9) . ?
N1 C3 1.439(9) . ?
N2 C7 1.444(8) . ?
N2 C4 1.453(9) . ?
C3 C4 1.513(10) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.514(12) . ?
C4 H4 0.90(7) . ?
C5 C6 1.402(12) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C7 1.452(12) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C9 1.363(10) . ?
C8 C13 1.408(11) . ?
C9 C10 1.363(12) . ?
C9 H9 0.9300 . ?
C10 C11 1.373(13) . ?
C10 H10 0.9300 . ?
C11 C12 1.366(13) . ?
C11 H11 0.9300 . ?
C12 C13 1.370(13) . ?
C12 H12 0.9300 . ?
C13 H13 0.9300 . ?
C14 C23 1.512(9) . ?
C14 C19 1.519(9) . ?
C14 C15 1.554(9) . ?
C14 H14 0.88(6) . ?
C15 C16 1.530(9) . ?
C15 H15 0.9800 . ?
C16 C17 1.499(9) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C18 1.537(9) . ?
C17 C20 1.575(9) . ?
C17 H17 1.01(6) . ?
C18 C19 1.552(9) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 C20 1.550(10) . ?
C19 H19 1.04(6) . ?
C20 C21 1.527(9) . ?
C20 C22 1.546(9) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 H22A 0.9600 . ?
C22 H22B 0.9600 . ?
C22 H22C 0.9600 . ?
C23 H23A 0.9700 . ?
C23 H23B 0.9700 . ?
C24 C25 1.367(11) . ?
C24 C29 1.394(11) . ?
C25 C26 1.361(13) . ?
C25 H25 0.9300 . ?
C26 C27 1.347(12) . ?
C26 H26 0.9300 . ?
C27 C28 1.358(12) . ?
C27 H27 0.9300 . ?
C28 C29 1.374(12) . ?
C28 H28 0.9300 . ?
C29 H29 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 P1 N2 106.7(3) . . ?
O1 P1 N1 102.7(3) . . ?
N2 P1 N1 90.6(4) . . ?
C24 S1 C15 105.0(4) . . ?
C23 O1 P1 120.8(4) . . ?
C8 N1 C3 120.6(8) . . ?
C8 N1 P1 123.9(7) . . ?
C3 N1 P1 115.5(7) . . ?
C7 N2 C4 108.8(7) . . ?
C7 N2 P1 123.9(6) . . ?
C4 N2 P1 117.1(7) . . ?
N1 C3 C4 107.6(8) . . ?
N1 C3 H3A 110.2 . . ?
C4 C3 H3A 110.2 . . ?
N1 C3 H3B 110.2 . . ?
C4 C3 H3B 110.2 . . ?
H3A C3 H3B 108.5 . . ?
N2 C4 C5 105.5(8) . . ?
N2 C4 C3 106.4(8) . . ?
C5 C4 C3 118.7(10) . . ?
N2 C4 H4 108.6 . . ?
C5 C4 H4 108.6 . . ?
C3 C4 H4 108.6 . . ?
C6 C5 C4 105.9(10) . . ?
C6 C5 H5A 110.6 . . ?
C4 C5 H5A 110.6 . . ?
C6 C5 H5B 110.6 . . ?
C4 C5 H5B 110.6 . . ?
H5A C5 H5B 108.7 . . ?
C5 C6 C7 109.3(10) . . ?
C5 C6 H6A 109.8 . . ?
C7 C6 H6A 109.8 . . ?
C5 C6 H6B 109.8 . . ?
C7 C6 H6B 109.8 . . ?
H6A C6 H6B 108.3 . . ?
N2 C7 C6 105.4(8) . . ?
N2 C7 H7A 110.7 . . ?
C6 C7 H7A 110.7 . . ?
N2 C7 H7B 110.7 . . ?
C6 C7 H7B 110.7 . . ?
H7A C7 H7B 108.8 . . ?
C9 C8 N1 120.7(11) . . ?
C9 C8 C13 117.4(10) . . ?
N1 C8 C13 121.9(12) . . ?
C8 C9 C10 123.7(10) . . ?
C8 C9 H9 118.1 . . ?
C10 C9 H9 118.1 . . ?
C9 C10 C11 118.2(11) . . ?
C9 C10 H10 120.9 . . ?
C11 C10 H10 120.9 . . ?
C12 C11 C10 119.9(13) . . ?
C12 C11 H11 120.1 . . ?
C10 C11 H11 120.1 . . ?
C11 C12 C13 121.8(12) . . ?
C11 C12 H12 119.1 . . ?
C13 C12 H12 119.1 . . ?
C12 C13 C8 118.8(11) . . ?
C12 C13 H13 120.6 . . ?
C8 C13 H13 120.6 . . ?
C23 C14 C19 113.9(6) . . ?
C23 C14 C15 112.3(7) . . ?
C19 C14 C15 110.5(7) . . ?
C23 C14 H14 106.5 . . ?
C19 C14 H14 106.5 . . ?
C15 C14 H14 106.5 . . ?
C16 C15 C14 116.9(7) . . ?
C16 C15 S1 106.3(6) . . ?
C14 C15 S1 113.5(6) . . ?
C16 C15 H15 106.5 . . ?
C14 C15 H15 106.5 . . ?
S1 C15 H15 106.5 . . ?
C17 C16 C15 112.4(6) . . ?
C17 C16 H16A 109.1 . . ?
C15 C16 H16A 109.1 . . ?
C17 C16 H16B 109.1 . . ?
C15 C16 H16B 109.1 . . ?
H16A C16 H16B 107.9 . . ?
C16 C17 C18 109.3(7) . . ?
C16 C17 C20 111.8(7) . . ?
C18 C17 C20 86.7(6) . . ?
C16 C17 H17 115.2 . . ?
C18 C17 H17 115.2 . . ?
C20 C17 H17 115.2 . . ?
C17 C18 C19 87.0(6) . . ?
C17 C18 H18A 114.2 . . ?
C19 C18 H18A 114.2 . . ?
C17 C18 H18B 114.2 . . ?
C19 C18 H18B 114.2 . . ?
H18A C18 H18B 111.3 . . ?
C14 C19 C18 107.3(6) . . ?
C14 C19 C20 114.3(6) . . ?
C18 C19 C20 87.1(6) . . ?
C14 C19 H19 114.9 . . ?
C18 C19 H19 114.9 . . ?
C20 C19 H19 114.9 . . ?
C21 C20 C22 108.5(7) . . ?
C21 C20 C19 122.5(7) . . ?
C22 C20 C19 109.8(7) . . ?
C21 C20 C17 117.7(7) . . ?
C22 C20 C17 110.8(7) . . ?
C19 C20 C17 85.7(6) . . ?
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 . . ?
O1 C23 C14 109.3(6) . . ?
O1 C23 H23A 109.8 . . ?
C14 C23 H23A 109.8 . . ?
O1 C23 H23B 109.8 . . ?
C14 C23 H23B 109.8 . . ?
H23A C23 H23B 108.3 . . ?
C25 C24 C29 119.0(10) . . ?
C25 C24 S1 121.1(12) . . ?
C29 C24 S1 119.9(12) . . ?
C24 C25 C26 122.3(11) . . ?
C24 C25 H25 118.8 . . ?
C26 C25 H25 118.8 . . ?
C27 C26 C25 118.1(12) . . ?
C27 C26 H26 120.9 . . ?
C25 C26 H26 120.9 . . ?
C26 C27 C28 121.5(13) . . ?
C26 C27 H27 119.3 . . ?
C28 C27 H27 119.3 . . ?
C27 C28 C29 121.2(12) . . ?
C27 C28 H28 119.4 . . ?
C29 C28 H28 119.4 . . ?
C24 C29 C28 117.8(11) . . ?
C24 C29 H29 121.1 . . ?
C28 C29 H29 121.1 . . ?

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
N2 P1 O1 C23 -47.2(6) . . . . ?
N1 P1 O1 C23 47.3(6) . . . . ?
O1 P1 N1 C8 71.2(6) . . . . ?
N2 P1 N1 C8 178.5(6) . . . . ?
O1 P1 N1 C3 -108.0(5) . . . . ?
N2 P1 N1 C3 -0.7(5) . . . . ?
O1 P1 N2 C7 -125.6(7) . . . . ?
N1 P1 N2 C7 131.0(8) . . . . ?
O1 P1 N2 C4 93.1(6) . . . . ?
N1 P1 N2 C4 -10.3(6) . . . . ?
C8 N1 C3 C4 -168.8(6) . . . . ?
P1 N1 C3 C4 10.5(8) . . . . ?
C7 N2 C4 C5 -2.3(10) . . . . ?
P1 N2 C4 C5 144.4(7) . . . . ?
C7 N2 C4 C3 -129.2(7) . . . . ?
P1 N2 C4 C3 17.5(9) . . . . ?
N1 C3 C4 N2 -16.3(9) . . . . ?
N1 C3 C4 C5 -134.9(9) . . . . ?
N2 C4 C5 C6 -11.6(13) . . . . ?
C3 C4 C5 C6 107.4(12) . . . . ?
C4 C5 C6 C7 21.4(14) . . . . ?
C4 N2 C7 C6 14.8(11) . . . . ?
P1 N2 C7 C6 -129.2(9) . . . . ?
C5 C6 C7 N2 -22.9(13) . . . . ?
C3 N1 C8 C9 -177.2(7) . . . . ?
P1 N1 C8 C9 3.7(10) . . . . ?
C3 N1 C8 C13 1.4(10) . . . . ?
P1 N1 C8 C13 -177.7(5) . . . . ?
N1 C8 C9 C10 -178.6(8) . . . . ?
C13 C8 C9 C10 2.7(13) . . . . ?
C8 C9 C10 C11 -1.1(14) . . . . ?
C9 C10 C11 C12 0.5(14) . . . . ?
C10 C11 C12 C13 -1.6(15) . . . . ?
C11 C12 C13 C8 3.2(14) . . . . ?
C9 C8 C13 C12 -3.6(11) . . . . ?
N1 C8 C13 C12 177.7(8) . . . . ?
C23 C14 C15 C16 -140.6(7) . . . . ?
C19 C14 C15 C16 -12.2(8) . . . . ?
C23 C14 C15 S1 95.2(7) . . . . ?
C19 C14 C15 S1 -136.4(6) . . . . ?
C24 S1 C15 C16 161.0(7) . . . . ?
C24 S1 C15 C14 -69.2(8) . . . . ?
C14 C15 C16 C17 9.9(9) . . . . ?
S1 C15 C16 C17 137.7(6) . . . . ?
C15 C16 C17 C18 -50.9(8) . . . . ?
C15 C16 C17 C20 43.3(9) . . . . ?
C16 C17 C18 C19 84.8(6) . . . . ?
C20 C17 C18 C19 -27.2(6) . . . . ?
C23 C14 C19 C18 -177.4(7) . . . . ?
C15 C14 C19 C18 55.1(8) . . . . ?
C23 C14 C19 C20 87.9(8) . . . . ?
C15 C14 C19 C20 -39.6(8) . . . . ?
C17 C18 C19 C14 -86.9(7) . . . . ?
C17 C18 C19 C20 27.7(6) . . . . ?
C14 C19 C20 C21 -39.7(10) . . . . ?
C18 C19 C20 C21 -147.4(7) . . . . ?
C14 C19 C20 C22 -168.8(6) . . . . ?
C18 C19 C20 C22 83.5(7) . . . . ?
C14 C19 C20 C17 80.7(7) . . . . ?
C18 C19 C20 C17 -27.0(6) . . . . ?
C16 C17 C20 C21 42.6(10) . . . . ?
C18 C17 C20 C21 152.1(8) . . . . ?
C16 C17 C20 C22 168.3(7) . . . . ?
C18 C17 C20 C22 -82.3(7) . . . . ?
C16 C17 C20 C19 -82.1(7) . . . . ?
C18 C17 C20 C19 27.3(6) . . . . ?
P1 O1 C23 C14 -170.0(5) . . . . ?
C19 C14 C23 O1 59.8(8) . . . . ?
C15 C14 C23 O1 -173.7(6) . . . . ?
C15 S1 C24 C25 114.5(7) . . . . ?
C15 S1 C24 C29 -63.4(8) . . . . ?
C29 C24 C25 C26 -3.0(14) . . . . ?
S1 C24 C25 C26 179.1(8) . . . . ?
C24 C25 C26 C27 2.9(17) . . . . ?
C25 C26 C27 C28 -2.2(17) . . . . ?
C26 C27 C28 C29 1.7(17) . . . . ?
C25 C24 C29 C28 2.3(13) . . . . ?
S1 C24 C29 C28 -179.8(7) . . . . ?
C27 C28 C29 C24 -1.7(15) . . . . ?

_refine_diff_density_max         0.178
_refine_diff_density_min         -0.175
_refine_diff_density_rms         0.037

####################################################################### 
# 
# 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_Gavr-74
_database_code_depnum_ccdc_archive 'CCDC 2235512'
loop_
_audit_author_name
_audit_author_address
'Vladimir Chernyshev'
;Lomonosov Moscow State University
Russia
;
_audit_update_record             
;
2023-01-11 deposited with the CCDC.	2024-07-18 downloaded from the CCDC.
;
# start Validation Reply Form
_vrf_PLAT340_Gavr-74             
;
PROBLEM: Low Bond Precision on C-C Bonds ............... 0.01567 Ang. 
RESPONSE: This crystal structure has been solved and refined with 
the use of laboratory powder diffraction data.
;
# end Validation Reply Form

_audit_creation_method           'MRIA, SHELXL-97'
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C27 H35 N2 O P S'
_chemical_formula_sum            'C27 H35 N2 O P S'
_chemical_formula_weight         466.60
_chemical_absolute_configuration syn

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
S S 0.3331 0.5567 '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'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   'P 21 21 21'
_symmetry_space_group_name_Hall  'P 2ac 2ab'

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

_cell_length_a                   26.0217(18)
_cell_length_b                   14.8896(12)
_cell_length_c                   6.6057(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2559.4(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    955
_cell_measurement_theta_min      3.40
_cell_measurement_theta_max      39.99

_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.211
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1000
_exptl_absorpt_coefficient_mu    1.868
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

#The next three fields give the specimen dimensions in mm.  The equatorial 
# plane contains the incident and diffracted beam.
_pd_spec_size_axial              15 # perpendicular to 
# equatorial plane

_pd_spec_size_equat              1 # parallel to 
# scattering vector 
# in transmission

_pd_spec_size_thick              1 # parallel to 
# scattering vector 
# in reflection

# The next five fields are character fields that describe the specimen.

_pd_spec_mounting                
; 
thin layer on the non-diffracting silicon plate
;
_pd_spec_mount_mode              reflection # options are 'reflection' 
# or 'transmission'

_pd_spec_shape                   flat_sheet # options are 'cylinder',
# 'flat_sheet' or 'irregular'

_pd_char_particle_morphology     plates
_pd_char_colour                  colorless # use ICDD colour descriptions

# The following three fields describe the preparation of the specimen. 
# The cooling rate is in K/min.  The pressure at which the sample was
# prepared is in kPa.  The temperature of preparation is in K.



_pd_prep_cool_rate               ?
_pd_prep_pressure                101
_pd_prep_temperature             295(2)


_exptl_special_details           
; 
 ? 
;

# This following item is used to identify the equipment used to record the
# powder pattern when the diffractogram was measured at a laboratory
# other than the authors' home institution, e.g. when neutron or synchrotron
# radiation is used.

_pd_instr_location               
;
A.N.Frumkin Institute of Physical Chemistry and Electrochemistry RAS,
Moscow
;

_diffrn_ambient_temperature      295(2)
_diffrn_source                   'Fine focus X-ray tube'
_diffrn_source_target            Cu

_diffrn_radiation_source         'line-focus sealed tube'
_diffrn_radiation_monochromator  ?
_diffrn_measurement_device       Empyrean
_diffrn_detector_type            ?



_diffrn_reflns_number            ?
_diffrn_reflns_limit_h_min       ?
_diffrn_reflns_limit_h_max       ?
_diffrn_reflns_limit_k_min       ?
_diffrn_reflns_limit_k_max       ?
_diffrn_reflns_limit_l_min       ?
_diffrn_reflns_limit_l_max       ?


_pd_meas_scan_method             cont # options are 'step', 'cont',
# 'tof', 'fixed' or
# 'disp' (= dispersive)
_pd_meas_special_details         
; ?
;
# The following six items are used for angular dispersive measurements only.

_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.5418

# The following four items give details of the measured (not processed)
# powder pattern.  Angles are in degrees.

_pd_meas_number_of_points        4354
_pd_meas_2theta_range_min        5.996
_pd_meas_2theta_range_max        79.997
_pd_meas_2theta_range_inc        0.017

# The following three items are used for time-of-flight measurements only.

_pd_instr_dist_src/spec          ?
_pd_instr_dist_spec/detc         ?
_pd_meas_2theta_fixed            ?

# The following fields are used to identify the programs used.

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    'simulated annealing (Zhukov et al., 2001)'
_computing_structure_refinement  MRIA
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'MRIA, SHELXL97 (Sheldrick, 2008)'

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

# 8. REFINEMENT DATA

# Use the next field to give any special details about the fitting of the
# powder pattern.

_pd_proc_ls_special_details      
; ?
;

# The next three items are given as text
_pd_proc_ls_profile_function     'split-type pseudo-Voigt (Toraya, 1986)'
_pd_proc_ls_pref_orient_corr     none
_pd_proc_ls_background_function  'Chebyshev polynomial up to the 5th order'

_pd_proc_ls_prof_R_factor        0.0298
_pd_proc_ls_prof_wR_factor       0.0386
_pd_proc_ls_prof_wR_expected     0.0160

_refine_special_details          
; 
?
;

_refine_ls_R_I_factor            0.0710
_refine_ls_structure_factor_coef Inet
_refine_ls_matrix_type           fullcycle
_refine_ls_weighting_scheme      sigma
_refine_ls_hydrogen_treatment    none
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_parameters     135
_refine_ls_number_restraints     111
_refine_ls_number_constraints    12

# The following item is the same as CHI, the square root of 'CHI squared = 5.823'
_refine_ls_goodness_of_fit_all   2.413

_refine_ls_restrained_S_all      ?
_refine_ls_restrained_S_obs      ?
_refine_ls_shift/su_max          .004
_refine_ls_shift/su_mean         .001


# The following four items apply to angular dispersive measurements.
# 2theta minimum, maximum and increment (in degrees) are for the 
# intensities used in the refinement.
_pd_proc_2theta_range_min        5.996
_pd_proc_2theta_range_max        79.997
_pd_proc_2theta_range_inc        0.017

_pd_proc_wavelength              1.5418

_pd_block_diffractogram_id       Gavr-74pattern # The id used for the block
# containing the powder 
# pattern profile (section 11).

# Give appropriate details in the next two text fields.
_pd_proc_info_excluded_regions   none
_pd_proc_info_data_reduction     ?

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

# 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
P1 P 1.02020(14) 0.8403(2) 0.8791(6) 0.0620(19) Uiso 1 1 d . . .
O1 O 0.9753(3) 0.9103(5) 0.7958(11) 0.069(4) Uiso 1 1 d . . .
N1 N 0.9913(3) 0.7713(6) 1.0538(15) 0.068(4) Uiso 1 1 d . . .
N2 N 1.0507(3) 0.9022(5) 1.0752(14) 0.067(5) Uiso 1 1 d . . .
C1 C 1.0513(4) 0.8525(8) 1.2673(17) 0.070(6) Uiso 1 1 d . . .
H1A H 1.0513 0.8937 1.3811 0.084 Uiso 1 1 calc . . .
H1B H 1.0816 0.8147 1.2759 0.084 Uiso 1 1 calc . . .
C2 C 1.0024(4) 0.7951(8) 1.2676(18) 0.073(6) Uiso 1 1 d . . .
H2 H 0.9737 0.8298 1.3239 0.088 Uiso 1 1 calc . . .
C3 C 1.0071(4) 0.7047(7) 1.3790(19) 0.070(6) Uiso 1 1 d . . .
H3A H 1.0356 0.7058 1.4737 0.084 Uiso 1 1 calc . . .
H3B H 0.9758 0.6911 1.4524 0.084 Uiso 1 1 calc . . .
C4 C 1.0165(4) 0.6353(8) 1.2116(17) 0.075(6) Uiso 1 1 d . . .
H4A H 1.0049 0.5760 1.2521 0.090 Uiso 1 1 calc . . .
H4B H 1.0525 0.6325 1.1748 0.090 Uiso 1 1 calc . . .
C5 C 0.9837(4) 0.6728(6) 1.0371(17) 0.069(6) Uiso 1 1 d . . .
H5A H 0.9956 0.6506 0.9073 0.083 Uiso 1 1 calc . . .
H5B H 0.9478 0.6569 1.0539 0.083 Uiso 1 1 calc . . .
C6 C 1.0870(4) 0.9715(7) 1.0470(18) 0.072(2) Uiso 1 1 d . . .
C7 C 1.0907(4) 1.0199(7) 0.8642(18) 0.072(2) Uiso 1 1 d . . .
H7 H 1.0699 1.0041 0.7554 0.086 Uiso 1 1 calc . . .
C8 C 1.1252(4) 1.0913(7) 0.8443(17) 0.072(2) Uiso 1 1 d . . .
H8 H 1.1284 1.1203 0.7202 0.086 Uiso 1 1 calc . . .
C9 C 1.1550(4) 1.1198(7) 1.0079(16) 0.072(2) Uiso 1 1 d . . .
H9 H 1.1764 1.1695 0.9966 0.086 Uiso 1 1 calc . . .
C10 C 1.1518(4) 1.0717(8) 1.1891(16) 0.072(2) Uiso 1 1 d . . .
H10 H 1.1714 1.0899 1.2995 0.086 Uiso 1 1 calc . . .
C11 C 1.1199(4) 0.9970(7) 1.2076(16) 0.072(2) Uiso 1 1 d . . .
H11 H 1.1202 0.9636 1.3266 0.086 Uiso 1 1 calc . . .
C12 C 0.9401(4) 0.9615(7) 0.9169(19) 0.077(6) Uiso 1 1 d . . .
H12A H 0.9518 1.0232 0.9272 0.092 Uiso 1 1 calc . . .
H12B H 0.9382 0.9365 1.0522 0.092 Uiso 1 1 calc . . .
C13 C 0.8871(4) 0.9583(8) 0.8163(16) 0.069(5) Uiso 1 1 d . . .
H13 H 0.8932 0.9692 0.6720 0.083 Uiso 1 1 calc . . .
C14 C 0.8530(4) 1.0379(7) 0.8899(18) 0.073(6) Uiso 1 1 d . . .
H14 H 0.8708 1.0593 1.0115 0.088 Uiso 1 1 calc . . .
C15 C 0.7989(4) 1.0108(7) 0.969(2) 0.080(6) Uiso 1 1 d . . .
H15A H 0.7969 1.0244 1.1129 0.096 Uiso 1 1 calc . . .
H15B H 0.7732 1.0468 0.9009 0.096 Uiso 1 1 calc . . .
C16 C 0.7864(4) 0.9112(7) 0.9377(19) 0.081(6) Uiso 1 1 d . . .
H16 H 0.7510 0.8939 0.9698 0.097 Uiso 1 1 calc . . .
C17 C 0.8289(5) 0.8487(7) 1.0299(17) 0.069(5) Uiso 1 1 d . . .
C18 C 0.8589(4) 0.8681(8) 0.8277(17) 0.074(5) Uiso 1 1 d . . .
H18 H 0.8785 0.8169 0.7751 0.089 Uiso 1 1 calc . . .
C19 C 0.8054(4) 0.8825(7) 0.7252(18) 0.075(6) Uiso 1 1 d . . .
H19A H 0.8047 0.9301 0.6249 0.090 Uiso 1 1 calc . . .
H19B H 0.7897 0.8280 0.6740 0.090 Uiso 1 1 calc . . .
C20 C 0.8105(4) 0.7503(8) 1.036(2) 0.082(6) Uiso 1 1 d . . .
H20A H 0.7962 0.7341 0.9073 0.123 Uiso 1 1 calc . . .
H20B H 0.7847 0.7437 1.1393 0.123 Uiso 1 1 calc . . .
H20C H 0.8391 0.7117 1.0665 0.123 Uiso 1 1 calc . . .
C21 C 0.8511(4) 0.8704(8) 1.2386(16) 0.079(6) Uiso 1 1 d . . .
H21A H 0.8630 0.9314 1.2404 0.119 Uiso 1 1 calc . . .
H21B H 0.8793 0.8307 1.2668 0.119 Uiso 1 1 calc . . .
H21C H 0.8249 0.8627 1.3396 0.119 Uiso 1 1 calc . . .
S1 S 0.86280(12) 1.1295(3) 0.7057(5) 0.0670(17) Uiso 1 1 d . . .
C22 C 0.8318(4) 1.2260(8) 0.8130(17) 0.078(2) Uiso 1 1 d . . .
C23 C 0.8198(4) 1.2400(8) 1.0184(19) 0.078(2) Uiso 1 1 d . . .
H23 H 0.8273 1.1957 1.1133 0.094 Uiso 1 1 calc . . .
C24 C 0.7967(4) 1.3202(6) 1.0801(18) 0.078(2) Uiso 1 1 d . . .
H24 H 0.7892 1.3290 1.2163 0.094 Uiso 1 1 calc . . .
C25 C 0.7848(4) 1.3873(7) 0.9401(18) 0.078(2) Uiso 1 1 d . . .
H25 H 0.7682 1.4395 0.9811 0.094 Uiso 1 1 calc . . .
C26 C 0.7983(4) 1.3747(8) 0.7371(18) 0.078(2) Uiso 1 1 d . . .
H26 H 0.7914 1.4196 0.6432 0.094 Uiso 1 1 calc . . .
C27 C 0.8220(5) 1.2959(8) 0.6743(18) 0.078(2) Uiso 1 1 d . . .
H27 H 0.8315 1.2892 0.5394 0.094 Uiso 1 1 calc . . .

_geom_special_details            
; 
 All esds (except the esd in the dihedral angle between two l.s. planes) 
 are estimated using the full covariance matrix.  The cell esds are taken 
 into account individually in the estimation of esds in distances, angles 
 and torsion angles; correlations between esds in cell parameters are only 
 used when they are defined by crystal symmetry.  An approximate (isotropic) 
 treatment of cell esds is used for estimating esds involving l.s. planes. 
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 O1 1.660(8) . ?
P1 N1 1.718(10) . ?
P1 N2 1.777(9) . ?
O1 C12 1.435(13) . ?
N1 C5 1.484(13) . ?
N1 C2 1.484(16) . ?
N2 C6 1.411(13) . ?
N2 C1 1.469(14) . ?
C1 C2 1.532(15) . ?
C2 C3 1.540(17) . ?
C3 C4 1.533(16) . ?
C4 C5 1.539(16) . ?
C6 C7 1.410(17) . ?
C6 C11 1.415(16) . ?
C7 C8 1.398(15) . ?
C8 C9 1.396(15) . ?
C9 C10 1.397(15) . ?
C10 C11 1.393(15) . ?
C12 C13 1.532(15) . ?
C13 C18 1.532(16) . ?
C13 C14 1.559(16) . ?
C14 C15 1.556(15) . ?
C14 S1 1.845(12) . ?
C15 C16 1.533(15) . ?
C16 C19 1.549(17) . ?
C16 C17 1.568(16) . ?
C17 C21 1.529(15) . ?
C17 C20 1.542(16) . ?
C17 C18 1.574(16) . ?
C18 C19 1.563(15) . ?
S1 C22 1.794(12) . ?
C22 C23 1.408(17) . ?
C22 C27 1.410(16) . ?
C23 C24 1.397(15) . ?
C24 C25 1.396(15) . ?
C25 C26 1.399(17) . ?
C26 C27 1.389(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
O1 P1 N1 106.9(4) . . ?
O1 P1 N2 103.3(4) . . ?
N1 P1 N2 90.9(5) . . ?
C12 O1 P1 126.7(7) . . ?
C5 N1 C2 109.4(9) . . ?
C5 N1 P1 126.8(8) . . ?
C2 N1 P1 114.3(7) . . ?
C6 N2 C1 118.4(9) . . ?
C6 N2 P1 125.6(8) . . ?
C1 N2 P1 111.9(6) . . ?
N2 C1 C2 105.8(9) . . ?
N1 C2 C1 107.1(9) . . ?
N1 C2 C3 105.1(9) . . ?
C1 C2 C3 115.0(9) . . ?
C4 C3 C2 104.9(10) . . ?
C3 C4 C5 102.0(9) . . ?
N1 C5 C4 103.2(9) . . ?
C7 C6 N2 122.2(10) . . ?
C7 C6 C11 117.6(10) . . ?
N2 C6 C11 120.1(10) . . ?
C8 C7 C6 120.9(10) . . ?
C9 C8 C7 121.0(10) . . ?
C8 C9 C10 118.3(10) . . ?
C11 C10 C9 121.3(10) . . ?
C10 C11 C6 120.6(10) . . ?
O1 C12 C13 108.4(9) . . ?
C12 C13 C18 115.9(9) . . ?
C12 C13 C14 110.7(9) . . ?
C18 C13 C14 112.3(9) . . ?
C15 C14 C13 115.0(9) . . ?
C15 C14 S1 122.6(8) . . ?
C13 C14 S1 106.1(8) . . ?
C16 C15 C14 113.4(9) . . ?
C15 C16 C19 108.8(9) . . ?
C15 C16 C17 111.8(9) . . ?
C19 C16 C17 87.9(8) . . ?
C21 C17 C20 107.0(9) . . ?
C21 C17 C16 119.4(9) . . ?
C20 C17 C16 110.8(9) . . ?
C21 C17 C18 122.6(9) . . ?
C20 C17 C18 110.6(9) . . ?
C16 C17 C18 84.9(8) . . ?
C13 C18 C19 106.6(9) . . ?
C13 C18 C17 116.1(9) . . ?
C19 C18 C17 87.2(8) . . ?
C16 C19 C18 86.0(8) . . ?
C22 S1 C14 105.6(5) . . ?
C23 C22 C27 118.5(10) . . ?
C23 C22 S1 126.8(9) . . ?
C27 C22 S1 114.6(9) . . ?
C24 C23 C22 120.2(11) . . ?
C25 C24 C23 120.9(11) . . ?
C24 C25 C26 118.9(10) . . ?
C27 C26 C25 120.8(10) . . ?
C26 C27 C22 120.6(11) . . ?

_refine_diff_density_max         0.51
_refine_diff_density_min         -0.43
_refine_diff_density_rms         0.22
####################################################################### 
# 
# 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_gavr80
_audit_block_doi                 10.5517/ccdc.csd.cc2g8g4c
_database_code_depnum_ccdc_archive 'CCDC 2272242'
loop_
_audit_author_name
_audit_author_address
Tafeenko
;MSU
Russia
;
_audit_update_record             
;
2023-06-25 deposited with the CCDC.	2024-07-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2016/6
_shelx_SHELXL_version_number     2016/6
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C25 H38 B F4 N2 O P Pd S'
_chemical_formula_sum            'C25 H38 B F4 N2 O P Pd S'
_chemical_formula_weight         638.81

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
B B 0.0013 0.0007 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Pd Pd -0.9988 1.0072 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

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

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

_cell_length_a                   10.7033(7)
_cell_length_b                   17.1681(8)
_cell_length_c                   15.4840(8)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2845.3(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    295(2)
_cell_measurement_reflns_used    17126
_cell_measurement_theta_min      2.24
_cell_measurement_theta_max      22.09

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.491
_exptl_crystal_F_000             1312
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          .23
_exptl_crystal_size_mid          .16
_exptl_crystal_size_min          .11
_exptl_absorpt_coefficient_mu    0.829
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
[c.f. r.h. blessing, acta cryst. (1995), a51, 33-38]
;

_exptl_absorpt_correction_T_min  0.405
_exptl_absorpt_correction_T_max  0.602
_diffrn_measurement_device_type  STOE
_diffrn_detector                 Pilatus100K
_diffrn_detector_type            STOE
_diffrn_detector_area_resol_mean 5.81
_diffrn_source                   'Mo LFF Sealed Tube'
_diffrn_source_voltage           50
_diffrn_source_current           40
_diffrn_source_power             2.000
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'plane graphite'
_diffrn_radiation_polarisn_norm  0
_diffrn_radiation_collimation    '0.5 mm diameter, monocapillary'
_diffrn_ambient_temperature      295
_diffrn_measurement_method       'rotation method'
_diffrn_reflns_number            38833
_diffrn_reflns_av_unetI/netI     0.1904
_diffrn_reflns_av_R_equivalents  0.0996
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.373
_diffrn_reflns_theta_max         28.300
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.982
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.982
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.976
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6891
_reflns_number_gt                2881
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.778
_reflns_Friedel_fraction_max     0.968
_reflns_Friedel_fraction_full    1.000

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

_computing_data_collection       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0378P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2016/6 (Sheldrick 2016)'
_refine_ls_extinction_coef       0.0019(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 886 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.04(3)
_chemical_absolute_configuration unk
_refine_ls_number_reflns         6891
_refine_ls_number_parameters     329
_refine_ls_number_restraints     10
_refine_ls_R_factor_all          0.1502
_refine_ls_R_factor_gt           0.0487
_refine_ls_wR_factor_ref         0.1056
_refine_ls_wR_factor_gt          0.0868
_refine_ls_goodness_of_fit_ref   0.769
_refine_ls_restrained_S_all      0.792
_refine_ls_shift/su_max          0.010
_refine_ls_shift/su_mean         0.001

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
Pd1 Pd 0.90777(7) 0.45511(4) 0.67820(5) 0.0499(2) Uani 1 1 d . . . . .
P1 P 0.7812(2) 0.53589(14) 0.60135(15) 0.0436(6) Uani 1 1 d . . . . .
S1 S 1.0630(3) 0.42883(12) 0.57495(17) 0.0610(8) Uani 1 1 d . . . . .
O1 O 0.8580(5) 0.6003(3) 0.5502(4) 0.0524(18) Uani 1 1 d . . . . .
N1 N 0.6936(7) 0.4903(4) 0.5306(5) 0.047(2) Uani 1 1 d . . . . .
N2 N 0.6629(7) 0.5849(4) 0.6445(5) 0.047(2) Uani 1 1 d . . . . .
C2 C 0.6982(11) 0.4054(5) 0.5141(8) 0.075(4) Uani 1 1 d . . . . .
H2A H 0.717468 0.394696 0.454060 0.090 Uiso 1 1 calc R U . . .
H2B H 0.760024 0.380309 0.550444 0.090 Uiso 1 1 calc R U . . .
C3 C 0.5710(16) 0.3790(7) 0.5361(11) 0.134(6) Uani 1 1 d . . . . .
H3A H 0.545963 0.336742 0.498307 0.161 Uiso 1 1 calc R U . . .
H3B H 0.568295 0.360610 0.595277 0.161 Uiso 1 1 calc R U . . .
C4 C 0.4882(14) 0.4450(10) 0.5252(16) 0.218(12) Uani 1 1 d . . . . .
H4A H 0.447033 0.442367 0.469500 0.261 Uiso 1 1 calc R U . . .
H4B H 0.424741 0.444929 0.569952 0.261 Uiso 1 1 calc R U . . .
C5 C 0.5627(10) 0.5147(6) 0.5310(8) 0.075(3) Uani 1 1 d . . . . .
H5 H 0.547790 0.545615 0.478780 0.090 Uiso 1 1 calc R U . . .
C6 C 0.5406(8) 0.5663(6) 0.6080(7) 0.068(3) Uani 1 1 d . . . . .
H6A H 0.497860 0.613535 0.590638 0.082 Uiso 1 1 calc R U . . .
H6B H 0.489540 0.539497 0.650415 0.082 Uiso 1 1 calc R U . . .
C7 C 0.6709(9) 0.6384(5) 0.7129(6) 0.045(2) Uani 1 1 d . . . . .
C8 C 0.7840(10) 0.6627(5) 0.7432(7) 0.058(3) Uani 1 1 d . . . . .
H8 H 0.857219 0.644654 0.717772 0.069 Uiso 1 1 calc R U . . .
C9 C 0.7898(10) 0.7138(5) 0.8112(8) 0.068(3) Uani 1 1 d . . . . .
H9 H 0.867077 0.727494 0.834070 0.082 Uiso 1 1 calc R U . . .
C10 C 0.6825(14) 0.7450(6) 0.8459(7) 0.079(4) Uani 1 1 d . . . . .
H10 H 0.687394 0.782790 0.888867 0.095 Uiso 1 1 calc R U . . .
C11 C 0.5740(12) 0.7212(6) 0.8182(8) 0.076(3) Uani 1 1 d . . . . .
H11 H 0.501875 0.740555 0.843987 0.091 Uiso 1 1 calc R U . . .
C12 C 0.5631(9) 0.6676(5) 0.7509(6) 0.060(3) Uani 1 1 d . . . . .
H12 H 0.484801 0.651672 0.731828 0.072 Uiso 1 1 calc R U . . .
C13 C 0.9868(9) 0.6140(5) 0.5683(8) 0.054(3) Uani 1 1 d . . . . .
H13 H 1.006542 0.598913 0.627783 0.065 Uiso 1 1 calc R U . . .
C14 C 1.0161(12) 0.7029(5) 0.5534(9) 0.088(4) Uani 1 1 d . . . . .
H14A H 0.944884 0.729885 0.528836 0.105 Uiso 1 1 calc R U . . .
H14B H 1.040049 0.728284 0.606926 0.105 Uiso 1 1 calc R U . . .
C15 C 1.1227(13) 0.7000(7) 0.4913(12) 0.125(6) Uani 1 1 d . . . . .
H15 H 1.135461 0.749607 0.461155 0.149 Uiso 1 1 calc R U . . .
C16 C 1.2386(13) 0.6712(8) 0.5341(13) 0.144(7) Uani 1 1 d . . . . .
H16A H 1.254591 0.698641 0.587749 0.173 Uiso 1 1 calc R U . . .
H16B H 1.310703 0.676181 0.496561 0.173 Uiso 1 1 calc R U . . .
C17 C 1.2059(11) 0.5851(6) 0.5506(10) 0.102(5) Uani 1 1 d . . . . .
H17A H 1.268209 0.550679 0.525762 0.123 Uiso 1 1 calc R U . . .
H17B H 1.198566 0.574351 0.611880 0.123 Uiso 1 1 calc R U . . .
C18 C 1.0795(10) 0.5761(5) 0.5048(7) 0.058(3) Uani 1 1 d . . . . .
C19 C 1.0858(13) 0.6342(6) 0.4303(9) 0.092(4) Uani 1 1 d . . . . .
C20 C 0.9634(13) 0.6449(6) 0.3797(8) 0.097(4) Uani 1 1 d . . . . .
H20A H 0.898119 0.660221 0.418683 0.146 Uiso 1 1 calc R U . . .
H20B H 0.941133 0.596648 0.352366 0.146 Uiso 1 1 calc R U . . .
H20C H 0.974518 0.684408 0.336571 0.146 Uiso 1 1 calc R U . . .
C21 C 1.1891(15) 0.6112(9) 0.3597(11) 0.156(8) Uani 1 1 d . . . . .
H21A H 1.162684 0.565337 0.329237 0.234 Uiso 1 1 calc R U . . .
H21B H 1.267248 0.601161 0.387959 0.234 Uiso 1 1 calc R U . . .
H21C H 1.199125 0.653342 0.319508 0.234 Uiso 1 1 calc R U . . .
C22 C 1.0481(10) 0.4930(5) 0.4816(7) 0.068(3) Uani 1 1 d . . . . .
H22A H 1.103683 0.475361 0.436154 0.082 Uiso 1 1 calc R U . . .
H22B H 0.963216 0.490631 0.459805 0.082 Uiso 1 1 calc R U . . .
C23 C 1.0297(11) 0.3376(5) 0.5248(8) 0.086(4) Uani 1 1 d . . . . .
H23A H 0.952099 0.341188 0.493984 0.129 Uiso 1 1 calc R U . . .
H23B H 1.023457 0.297865 0.568215 0.129 Uiso 1 1 calc R U . . .
H23C H 1.095605 0.324693 0.485278 0.129 Uiso 1 1 calc R U . . .
C24 C 0.9950(17) 0.3867(8) 0.7824(9) 0.114(5) Uani 1 1 d . . . . .
H24A H 1.046793 0.429285 0.772488 0.136 Uiso 1 1 calc R U . . .
H24B H 1.028070 0.336591 0.782086 0.136 Uiso 1 1 calc R U . . .
C25 C 0.8141(13) 0.4663(9) 0.7991(7) 0.116(5) Uani 1 1 d . . . . .
H25A H 0.859707 0.511628 0.789770 0.140 Uiso 1 1 calc R U . . .
H25B H 0.728727 0.469053 0.809682 0.140 Uiso 1 1 calc R U . . .
C26 C 0.8709(19) 0.3977(9) 0.7972(10) 0.130(6) Uani 1 1 d . . . . .
H26 H 0.822195 0.353678 0.806836 0.156 Uiso 1 1 calc R U . . .
F1 F 0.3574(18) 0.2929(9) 0.3805(14) 0.421(18) Uani 1 1 d D . . . .
F2 F 0.2382(13) 0.3896(9) 0.3574(13) 0.363(16) Uani 1 1 d D . . . .
F3 F 0.4156(11) 0.3815(10) 0.2908(9) 0.303(9) Uani 1 1 d D . . . .
F4 F 0.2569(14) 0.3034(11) 0.2580(12) 0.367(13) Uani 1 1 d D . . . .
B1 B 0.3183(14) 0.3413(9) 0.3201(11) 0.212(15) Uani 1 1 d D . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Pd1 C26 2.127(14) . ?
Pd1 C25 2.132(11) . ?
Pd1 C24 2.203(11) . ?
Pd1 P1 2.275(2) . ?
Pd1 S1 2.350(3) . ?
P1 O1 1.590(6) . ?
P1 N1 1.640(7) . ?
P1 N2 1.661(8) . ?
S1 C23 1.784(9) . ?
S1 C22 1.825(10) . ?
O1 C13 1.426(10) . ?
N1 C5 1.462(12) . ?
N1 C2 1.479(10) . ?
N2 C7 1.405(11) . ?
N2 C6 1.461(11) . ?
C2 C3 1.474(18) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.45(2) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 C5 1.441(16) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.505(13) . ?
C5 H5 0.9800 . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.364(12) . ?
C7 C12 1.389(12) . ?
C8 C9 1.371(13) . ?
C8 H8 0.9300 . ?
C9 C10 1.377(15) . ?
C9 H9 0.9300 . ?
C10 C11 1.304(15) . ?
C10 H10 0.9300 . ?
C11 C12 1.395(13) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 C18 1.541(14) . ?
C13 C14 1.576(11) . ?
C13 H13 0.9800 . ?
C14 C15 1.493(17) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.492(17) . ?
C15 C19 1.526(19) . ?
C15 H15 0.9800 . ?
C16 C17 1.540(15) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 C18 1.535(16) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 C22 1.509(12) . ?
C18 C19 1.526(14) . ?
C19 C20 1.537(17) . ?
C19 C21 1.604(17) . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 0.9600 . ?
C22 H22A 0.9700 . ?
C22 H22B 0.9700 . ?
C23 H23A 0.9600 . ?
C23 H23B 0.9600 . ?
C23 H23C 0.9600 . ?
C24 C26 1.362(18) . ?
C24 H24A 0.9300 . ?
C24 H24B 0.9300 . ?
C25 C26 1.325(17) . ?
C25 H25A 0.9300 . ?
C25 H25B 0.9300 . ?
C26 H26 0.9300 . ?
F1 B1 1.320(12) . ?
F2 B1 1.325(12) . ?
F3 B1 1.330(11) . ?
F4 B1 1.334(11) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C26 Pd1 C25 36.3(5) . . ?
C26 Pd1 C24 36.6(5) . . ?
C25 Pd1 C24 66.7(5) . . ?
C26 Pd1 P1 128.7(5) . . ?
C25 Pd1 P1 97.1(4) . . ?
C24 Pd1 P1 163.8(5) . . ?
C26 Pd1 S1 129.2(5) . . ?
C25 Pd1 S1 161.3(4) . . ?
C24 Pd1 S1 95.5(5) . . ?
P1 Pd1 S1 100.51(8) . . ?
O1 P1 N1 107.2(4) . . ?
O1 P1 N2 104.1(3) . . ?
N1 P1 N2 94.3(4) . . ?
O1 P1 Pd1 112.1(2) . . ?
N1 P1 Pd1 113.5(3) . . ?
N2 P1 Pd1 123.5(3) . . ?
C23 S1 C22 99.7(5) . . ?
C23 S1 Pd1 108.8(4) . . ?
C22 S1 Pd1 111.2(3) . . ?
C13 O1 P1 121.1(6) . . ?
C5 N1 C2 108.3(8) . . ?
C5 N1 P1 114.1(6) . . ?
C2 N1 P1 124.5(7) . . ?
C7 N2 C6 119.3(7) . . ?
C7 N2 P1 126.0(6) . . ?
C6 N2 P1 114.6(6) . . ?
C3 C2 N1 103.4(10) . . ?
C3 C2 H2A 111.1 . . ?
N1 C2 H2A 111.1 . . ?
C3 C2 H2B 111.1 . . ?
N1 C2 H2B 111.1 . . ?
H2A C2 H2B 109.0 . . ?
C4 C3 C2 107.3(10) . . ?
C4 C3 H3A 110.2 . . ?
C2 C3 H3A 110.2 . . ?
C4 C3 H3B 110.3 . . ?
C2 C3 H3B 110.2 . . ?
H3A C3 H3B 108.5 . . ?
C5 C4 C3 107.7(11) . . ?
C5 C4 H4A 110.2 . . ?
C3 C4 H4A 110.2 . . ?
C5 C4 H4B 110.2 . . ?
C3 C4 H4B 110.2 . . ?
H4A C4 H4B 108.5 . . ?
C4 C5 N1 107.0(9) . . ?
C4 C5 C6 116.8(12) . . ?
N1 C5 C6 108.8(8) . . ?
C4 C5 H5 108.0 . . ?
N1 C5 H5 108.0 . . ?
C6 C5 H5 108.0 . . ?
N2 C6 C5 107.1(7) . . ?
N2 C6 H6A 110.3 . . ?
C5 C6 H6A 110.3 . . ?
N2 C6 H6B 110.3 . . ?
C5 C6 H6B 110.3 . . ?
H6A C6 H6B 108.5 . . ?
C8 C7 C12 118.8(8) . . ?
C8 C7 N2 120.9(9) . . ?
C12 C7 N2 120.3(8) . . ?
C7 C8 C9 120.0(10) . . ?
C7 C8 H8 120.0 . . ?
C9 C8 H8 120.0 . . ?
C8 C9 C10 120.8(10) . . ?
C8 C9 H9 119.6 . . ?
C10 C9 H9 119.6 . . ?
C11 C10 C9 119.5(10) . . ?
C11 C10 H10 120.3 . . ?
C9 C10 H10 120.3 . . ?
C10 C11 C12 121.8(11) . . ?
C10 C11 H11 119.1 . . ?
C12 C11 H11 119.1 . . ?
C7 C12 C11 119.0(10) . . ?
C7 C12 H12 120.5 . . ?
C11 C12 H12 120.5 . . ?
O1 C13 C18 115.3(9) . . ?
O1 C13 C14 108.9(8) . . ?
C18 C13 C14 100.8(8) . . ?
O1 C13 H13 110.5 . . ?
C18 C13 H13 110.5 . . ?
C14 C13 H13 110.5 . . ?
C15 C14 C13 102.4(9) . . ?
C15 C14 H14A 111.3 . . ?
C13 C14 H14A 111.3 . . ?
C15 C14 H14B 111.3 . . ?
C13 C14 H14B 111.3 . . ?
H14A C14 H14B 109.2 . . ?
C16 C15 C14 111.1(15) . . ?
C16 C15 C19 104.1(13) . . ?
C14 C15 C19 103.1(10) . . ?
C16 C15 H15 112.6 . . ?
C14 C15 H15 112.6 . . ?
C19 C15 H15 112.6 . . ?
C15 C16 C17 101.7(10) . . ?
C15 C16 H16A 111.4 . . ?
C17 C16 H16A 111.4 . . ?
C15 C16 H16B 111.4 . . ?
C17 C16 H16B 111.4 . . ?
H16A C16 H16B 109.3 . . ?
C18 C17 C16 102.7(10) . . ?
C18 C17 H17A 111.2 . . ?
C16 C17 H17A 111.2 . . ?
C18 C17 H17B 111.2 . . ?
C16 C17 H17B 111.2 . . ?
H17A C17 H17B 109.1 . . ?
C22 C18 C19 116.6(10) . . ?
C22 C18 C17 113.6(9) . . ?
C19 C18 C17 104.2(9) . . ?
C22 C18 C13 114.0(8) . . ?
C19 C18 C13 103.6(8) . . ?
C17 C18 C13 103.3(9) . . ?
C15 C19 C18 91.6(11) . . ?
C15 C19 C20 116.6(10) . . ?
C18 C19 C20 115.2(10) . . ?
C15 C19 C21 115.2(12) . . ?
C18 C19 C21 112.7(10) . . ?
C20 C19 C21 105.6(12) . . ?
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 . . ?
C18 C22 S1 111.3(7) . . ?
C18 C22 H22A 109.4 . . ?
S1 C22 H22A 109.4 . . ?
C18 C22 H22B 109.4 . . ?
S1 C22 H22B 109.4 . . ?
H22A C22 H22B 108.0 . . ?
S1 C23 H23A 109.5 . . ?
S1 C23 H23B 109.5 . . ?
H23A C23 H23B 109.5 . . ?
S1 C23 H23C 109.5 . . ?
H23A C23 H23C 109.5 . . ?
H23B C23 H23C 109.5 . . ?
C26 C24 Pd1 68.7(8) . . ?
C26 C24 H24A 120.0 . . ?
Pd1 C24 H24A 73.3 . . ?
C26 C24 H24B 120.0 . . ?
Pd1 C24 H24B 130.6 . . ?
H24A C24 H24B 120.0 . . ?
C26 C25 Pd1 71.7(9) . . ?
C26 C25 H25A 120.0 . . ?
Pd1 C25 H25A 72.1 . . ?
C26 C25 H25B 120.0 . . ?
Pd1 C25 H25B 128.4 . . ?
H25A C25 H25B 120.0 . . ?
C25 C26 C24 125.0(17) . . ?
C25 C26 Pd1 72.1(8) . . ?
C24 C26 Pd1 74.7(9) . . ?
C25 C26 H26 117.5 . . ?
C24 C26 H26 117.5 . . ?
Pd1 C26 H26 128.2 . . ?
F1 B1 F2 106.9(12) . . ?
F1 B1 F3 108.7(12) . . ?
F2 B1 F3 109.3(11) . . ?
F1 B1 F4 111.1(11) . . ?
F2 B1 F4 107.5(11) . . ?
F3 B1 F4 113.2(12) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 P1 O1 C13 -138.2(7) . . . . ?
N2 P1 O1 C13 122.7(7) . . . . ?
Pd1 P1 O1 C13 -13.1(8) . . . . ?
O1 P1 N1 C5 -101.8(7) . . . . ?
N2 P1 N1 C5 4.4(7) . . . . ?
Pd1 P1 N1 C5 133.9(6) . . . . ?
O1 P1 N1 C2 121.8(9) . . . . ?
N2 P1 N1 C2 -132.1(9) . . . . ?
Pd1 P1 N1 C2 -2.5(9) . . . . ?
O1 P1 N2 C7 -71.2(8) . . . . ?
N1 P1 N2 C7 179.9(7) . . . . ?
Pd1 P1 N2 C7 58.0(8) . . . . ?
O1 P1 N2 C6 111.4(7) . . . . ?
N1 P1 N2 C6 2.5(7) . . . . ?
Pd1 P1 N2 C6 -119.4(6) . . . . ?
C5 N1 C2 C3 -19.6(14) . . . . ?
P1 N1 C2 C3 119.0(10) . . . . ?
N1 C2 C3 C4 25.3(17) . . . . ?
C2 C3 C4 C5 -22(2) . . . . ?
C3 C4 C5 N1 9(2) . . . . ?
C3 C4 C5 C6 -112.7(15) . . . . ?
C2 N1 C5 C4 6.7(16) . . . . ?
P1 N1 C5 C4 -136.6(12) . . . . ?
C2 N1 C5 C6 133.7(9) . . . . ?
P1 N1 C5 C6 -9.7(10) . . . . ?
C7 N2 C6 C5 174.2(8) . . . . ?
P1 N2 C6 C5 -8.2(10) . . . . ?
C4 C5 C6 N2 131.8(13) . . . . ?
N1 C5 C6 N2 10.7(11) . . . . ?
C6 N2 C7 C8 -173.8(9) . . . . ?
P1 N2 C7 C8 8.9(12) . . . . ?
C6 N2 C7 C12 6.1(12) . . . . ?
P1 N2 C7 C12 -171.2(7) . . . . ?
C12 C7 C8 C9 1.4(14) . . . . ?
N2 C7 C8 C9 -178.7(8) . . . . ?
C7 C8 C9 C10 -4.3(15) . . . . ?
C8 C9 C10 C11 5.2(16) . . . . ?
C9 C10 C11 C12 -3.3(17) . . . . ?
C8 C7 C12 C11 0.5(14) . . . . ?
N2 C7 C12 C11 -179.4(8) . . . . ?
C10 C11 C12 C7 0.5(15) . . . . ?
P1 O1 C13 C18 100.2(9) . . . . ?
P1 O1 C13 C14 -147.4(7) . . . . ?
O1 C13 C14 C15 -125.5(11) . . . . ?
C18 C13 C14 C15 -3.8(12) . . . . ?
C13 C14 C15 C16 -70.9(14) . . . . ?
C13 C14 C15 C19 40.1(13) . . . . ?
C14 C15 C16 C17 69.4(16) . . . . ?
C19 C15 C16 C17 -40.9(16) . . . . ?
C15 C16 C17 C18 6.0(16) . . . . ?
C16 C17 C18 C22 158.3(11) . . . . ?
C16 C17 C18 C19 30.4(13) . . . . ?
C16 C17 C18 C13 -77.6(11) . . . . ?
O1 C13 C18 C22 -44.2(12) . . . . ?
C14 C13 C18 C22 -161.2(9) . . . . ?
O1 C13 C18 C19 83.6(10) . . . . ?
C14 C13 C18 C19 -33.5(11) . . . . ?
O1 C13 C18 C17 -168.0(8) . . . . ?
C14 C13 C18 C17 75.0(9) . . . . ?
C16 C15 C19 C18 57.3(13) . . . . ?
C14 C15 C19 C18 -58.7(11) . . . . ?
C16 C15 C19 C20 176.6(11) . . . . ?
C14 C15 C19 C20 60.6(13) . . . . ?
C16 C15 C19 C21 -58.7(15) . . . . ?
C14 C15 C19 C21 -174.8(11) . . . . ?
C22 C18 C19 C15 -178.2(10) . . . . ?
C17 C18 C19 C15 -52.1(11) . . . . ?
C13 C18 C19 C15 55.7(10) . . . . ?
C22 C18 C19 C20 61.3(14) . . . . ?
C17 C18 C19 C20 -172.6(10) . . . . ?
C13 C18 C19 C20 -64.8(12) . . . . ?
C22 C18 C19 C21 -59.9(15) . . . . ?
C17 C18 C19 C21 66.1(13) . . . . ?
C13 C18 C19 C21 173.9(11) . . . . ?
C19 C18 C22 S1 172.9(8) . . . . ?
C17 C18 C22 S1 51.8(11) . . . . ?
C13 C18 C22 S1 -66.3(10) . . . . ?
C23 S1 C22 C18 -176.7(8) . . . . ?
Pd1 S1 C22 C18 68.6(8) . . . . ?
Pd1 C25 C26 C24 55.6(16) . . . . ?
Pd1 C24 C26 C25 -54.5(15) . . . . ?

_refine_diff_density_max         0.560
_refine_diff_density_min         -0.412
_refine_diff_density_rms         0.078

