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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_Sal4_a
_database_code_depnum_ccdc_archive 'CCDC 1914343'
loop_
_audit_author_name
_audit_author_address
'Daut Islamov'
;IOPC
Russia
;
_audit_update_record             
;
2019-05-07 deposited with the CCDC.	2019-07-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            
'Diethyl 2,2-bis(2-((1R,5R,6S,7S,10S,11S)-1,10-epoxyguaia-3-ene-6,12-olid)methyl)malonate'
_chemical_formula_moiety         'C37 H48 O10'
_chemical_formula_sum            'C37 H48 O10'
_chemical_melting_point          ?

_exptl_crystal_description       prism
_exptl_crystal_colour            Colourless
_diffrn_ambient_temperature      100(2)
_chemical_formula_weight         652.75

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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'
_chemical_absolute_configuration syn

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'

_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.
;

_cell_length_a                   9.7510(7)
_cell_length_b                   16.7972(13)
_cell_length_c                   20.8431(14)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     3413.9(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3968
_cell_measurement_theta_min      2.61
_cell_measurement_theta_max      26.41
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.270
_exptl_crystal_F_000             1400
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.521
_exptl_crystal_size_mid          0.409
_exptl_crystal_size_min          0.246
_exptl_absorpt_coefficient_mu    0.091
_shelx_estimated_absorpt_T_min   0.954
_shelx_estimated_absorpt_T_max   0.978
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6770
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed X-ray tube'
_diffrn_measurement_device_type  'Bruker Kappa APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            28331
_diffrn_reflns_av_unetI/netI     0.0972
_diffrn_reflns_av_R_equivalents  0.0840
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       21
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         1.557
_diffrn_reflns_theta_max         27.141
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             7536
_reflns_number_gt                5216
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.787
_reflns_Friedel_fraction_max     0.995
_reflns_Friedel_fraction_full    1.000

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

_computing_data_collection       'APEX2  v2, 1-4  (Bruker AXS, 2005-2007)'
_computing_cell_refinement       'APEX2  v2, 1-4  (Bruker AXS, 2005-2007)'
_computing_data_reduction        'SAINT NT v6.0 (Bruker AXS, 2003)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'MERCURY 4.1 (Macrae, 2006)'
_computing_publication_material  'enCIFer (Allen et al. 2004)'
_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)+(0.0791P)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-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.036(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 1592 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.9(8)
_refine_ls_number_reflns         7536
_refine_ls_number_parameters     431
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0958
_refine_ls_R_factor_gt           0.0616
_refine_ls_wR_factor_ref         0.1650
_refine_ls_wR_factor_gt          0.1310
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_restrained_S_all      1.060
_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
C1 C 0.8066(5) 0.6498(3) 0.2874(2) 0.0249(11) Uani 1 1 d . . . . .
C2 C 0.8810(6) 0.6435(3) 0.2232(2) 0.0327(13) Uani 1 1 d . . . . .
H2A H 0.8371 0.6035 0.1950 0.039 Uiso 1 1 calc R U . . .
H2B H 0.8829 0.6955 0.2008 0.039 Uiso 1 1 calc R U . . .
C3 C 1.0214(6) 0.6181(3) 0.2422(2) 0.0333(13) Uani 1 1 d . . . . .
H3 H 1.0890 0.6014 0.2123 0.040 Uiso 1 1 calc R U . . .
C4 C 1.0430(5) 0.6211(3) 0.3047(2) 0.0272(11) Uani 1 1 d . . . . .
C5 C 0.9166(5) 0.6532(3) 0.3395(2) 0.0250(11) Uani 1 1 d . . . . .
H5 H 0.9337 0.7105 0.3498 0.030 Uiso 1 1 calc R U . . .
C6 C 0.8706(5) 0.6117(3) 0.4012(2) 0.0227(10) Uani 1 1 d . . . . .
H6 H 0.8279 0.5592 0.3905 0.027 Uiso 1 1 calc R U . . .
C7 C 0.7720(5) 0.6605(3) 0.4424(2) 0.0204(10) Uani 1 1 d . . . . .
H7 H 0.8083 0.7160 0.4454 0.025 Uiso 1 1 calc R U . . .
C8 C 0.6258(5) 0.6646(3) 0.4172(2) 0.0252(11) Uani 1 1 d . . . . .
H8A H 0.5665 0.6878 0.4509 0.030 Uiso 1 1 calc R U . . .
H8B H 0.5932 0.6097 0.4089 0.030 Uiso 1 1 calc R U . . .
C9 C 0.6090(5) 0.7134(3) 0.3558(2) 0.0283(11) Uani 1 1 d . . . . .
H9A H 0.5100 0.7240 0.3497 0.034 Uiso 1 1 calc R U . . .
H9B H 0.6545 0.7655 0.3625 0.034 Uiso 1 1 calc R U . . .
C10 C 0.6640(5) 0.6780(3) 0.2941(2) 0.0258(11) Uani 1 1 d . . . . .
C11 C 0.7927(5) 0.6198(3) 0.5081(2) 0.0217(10) Uani 1 1 d . . . . .
H11 H 0.7411 0.5683 0.5081 0.026 Uiso 1 1 calc R U . . .
C12 C 0.9451(5) 0.6015(3) 0.5057(2) 0.0256(11) Uani 1 1 d . . . . .
C13 C 0.7528(5) 0.6670(3) 0.56876(19) 0.0211(10) Uani 1 1 d . . . . .
H13A H 0.6838 0.7076 0.5567 0.025 Uiso 1 1 calc R U . . .
H13B H 0.8350 0.6955 0.5846 0.025 Uiso 1 1 calc R U . . .
C14 C 1.1762(5) 0.6030(3) 0.3374(2) 0.0342(12) Uani 1 1 d . . . . .
H14A H 1.1666 0.5544 0.3630 0.051 Uiso 1 1 calc R U . . .
H14B H 1.2012 0.6475 0.3655 0.051 Uiso 1 1 calc R U . . .
H14C H 1.2480 0.5954 0.3051 0.051 Uiso 1 1 calc R U . . .
C15 C 0.5877(6) 0.7047(3) 0.2355(2) 0.0345(13) Uani 1 1 d . . . . .
H15A H 0.6236 0.6768 0.1978 0.052 Uiso 1 1 calc R U . . .
H15B H 0.5996 0.7622 0.2299 0.052 Uiso 1 1 calc R U . . .
H15C H 0.4900 0.6925 0.2405 0.052 Uiso 1 1 calc R U . . .
C16 C 0.6940(4) 0.6160(3) 0.6241(2) 0.0179(9) Uani 1 1 d . . . . .
C17 C 0.5560(5) 0.5775(3) 0.6071(2) 0.0217(10) Uani 1 1 d . . . . .
C18 C 0.3460(5) 0.5962(3) 0.5502(2) 0.0281(11) Uani 1 1 d . . . . .
H18A H 0.2924 0.6423 0.5343 0.034 Uiso 1 1 calc R U . . .
H18B H 0.3029 0.5774 0.5904 0.034 Uiso 1 1 calc R U . . .
C19 C 0.3422(5) 0.5318(3) 0.5019(3) 0.0383(13) Uani 1 1 d . . . . .
H19A H 0.3926 0.5485 0.4635 0.057 Uiso 1 1 calc R U . . .
H19B H 0.2467 0.5204 0.4905 0.057 Uiso 1 1 calc R U . . .
H19C H 0.3847 0.4838 0.5198 0.057 Uiso 1 1 calc R U . . .
C1' C 0.6105(4) 0.6401(2) 0.9614(2) 0.0186(10) Uani 1 1 d . . . . .
C2' C 0.5415(4) 0.6440(3) 1.0267(2) 0.0220(10) Uani 1 1 d . . . . .
H2'1 H 0.5697 0.5990 1.0544 0.026 Uiso 1 1 calc R U . . .
H2'2 H 0.5620 0.6948 1.0488 0.026 Uiso 1 1 calc R U . . .
C3' C 0.3922(5) 0.6384(3) 1.0087(2) 0.0242(10) Uani 1 1 d . . . . .
H3' H 0.3213 0.6287 1.0389 0.029 Uiso 1 1 calc R U . . .
C4' C 0.3694(4) 0.6482(3) 0.9463(2) 0.0211(10) Uani 1 1 d . . . . .
C5' C 0.5026(4) 0.6648(3) 0.9108(2) 0.0178(9) Uani 1 1 d . . . . .
H5' H 0.5100 0.7236 0.9044 0.021 Uiso 1 1 calc R U . . .
C6' C 0.5241(4) 0.6249(3) 0.84620(19) 0.0185(9) Uani 1 1 d . . . . .
H6' H 0.5342 0.5661 0.8526 0.022 Uiso 1 1 calc R U . . .
C7' C 0.6447(4) 0.6556(3) 0.8077(2) 0.0185(10) Uani 1 1 d . . . . .
H7' H 0.6430 0.7151 0.8089 0.022 Uiso 1 1 calc R U . . .
C8' C 0.7851(4) 0.6280(3) 0.8288(2) 0.0218(10) Uani 1 1 d . . . . .
H8'1 H 0.8524 0.6414 0.7950 0.026 Uiso 1 1 calc R U . . .
H8'2 H 0.7838 0.5693 0.8334 0.026 Uiso 1 1 calc R U . . .
C9' C 0.8326(5) 0.6646(3) 0.8920(2) 0.0242(10) Uani 1 1 d . . . . .
H9'1 H 0.9317 0.6532 0.8968 0.029 Uiso 1 1 calc R U . . .
H9'2 H 0.8228 0.7231 0.8884 0.029 Uiso 1 1 calc R U . . .
C10' C 0.7611(4) 0.6385(3) 0.9534(2) 0.0211(10) Uani 1 1 d . . . . .
C11' C 0.6023(4) 0.6286(3) 0.7402(2) 0.0193(10) Uani 1 1 d . . . . .
H11' H 0.6180 0.5699 0.7365 0.023 Uiso 1 1 calc R U . . .
C12' C 0.4483(5) 0.6440(3) 0.7434(2) 0.0205(10) Uani 1 1 d . . . . .
C13' C 0.6707(4) 0.6699(2) 0.68359(19) 0.0186(9) Uani 1 1 d . . . . .
H13C H 0.7605 0.6910 0.6978 0.022 Uiso 1 1 calc R U . . .
H13D H 0.6134 0.7158 0.6706 0.022 Uiso 1 1 calc R U . . .
C14' C 0.2315(4) 0.6509(3) 0.9149(2) 0.0286(12) Uani 1 1 d . . . . .
H14D H 0.1598 0.6491 0.9478 0.043 Uiso 1 1 calc R U . . .
H14E H 0.2216 0.6051 0.8861 0.043 Uiso 1 1 calc R U . . .
H14F H 0.2229 0.7003 0.8901 0.043 Uiso 1 1 calc R U . . .
C15' C 0.8509(5) 0.6437(3) 1.0130(2) 0.0237(10) Uani 1 1 d . . . . .
H15D H 0.7979 0.6269 1.0506 0.035 Uiso 1 1 calc R U . . .
H15E H 0.8818 0.6987 1.0188 0.035 Uiso 1 1 calc R U . . .
H15F H 0.9307 0.6088 1.0078 0.035 Uiso 1 1 calc R U . . .
C17' C 0.7955(5) 0.5493(3) 0.6389(2) 0.0198(10) Uani 1 1 d . . . . .
C18' C 1.0024(5) 0.5151(3) 0.6908(2) 0.0256(11) Uani 1 1 d . . . . .
H18C H 1.0487 0.5044 0.6494 0.031 Uiso 1 1 calc R U . . .
H18D H 0.9662 0.4643 0.7078 0.031 Uiso 1 1 calc R U . . .
C19' C 1.1011(6) 0.5508(3) 0.7373(3) 0.0419(14) Uani 1 1 d . . . . .
H19D H 1.1282 0.6039 0.7224 0.063 Uiso 1 1 calc R U . . .
H19E H 1.1825 0.5168 0.7405 0.063 Uiso 1 1 calc R U . . .
H19F H 1.0575 0.5551 0.7795 0.063 Uiso 1 1 calc R U . . .
O1 O 0.6948(4) 0.59255(18) 0.29659(15) 0.0278(8) Uani 1 1 d . . . . .
O2 O 0.9881(3) 0.59939(19) 0.44387(14) 0.0265(8) Uani 1 1 d . . . . .
O3 O 1.0239(3) 0.5940(2) 0.54974(16) 0.0355(9) Uani 1 1 d . . . . .
O4 O 0.4872(3) 0.62170(19) 0.56359(14) 0.0245(8) Uani 1 1 d . . . . .
O5 O 0.5119(3) 0.51824(19) 0.63177(15) 0.0266(8) Uani 1 1 d . . . . .
O1' O 0.6816(3) 0.56528(17) 0.94856(14) 0.0205(7) Uani 1 1 d . . . . .
O2' O 0.4060(3) 0.64025(18) 0.80519(14) 0.0215(7) Uani 1 1 d . . . . .
O3' O 0.3708(3) 0.66058(18) 0.70084(15) 0.0248(7) Uani 1 1 d . . . . .
O4' O 0.8908(3) 0.57194(17) 0.68166(14) 0.0214(7) Uani 1 1 d . . . . .
O5' O 0.7940(3) 0.48531(19) 0.61278(15) 0.0279(8) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 O1 1.466(6) . ?
C1 C10 1.475(7) . ?
C1 C2 1.527(6) . ?
C1 C5 1.527(7) . ?
C2 C3 1.488(8) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.320(7) . ?
C3 H3 0.9500 . ?
C4 C14 1.498(7) . ?
C4 C5 1.529(6) . ?
C5 C6 1.530(6) . ?
C5 H5 1.0000 . ?
C6 O2 1.465(5) . ?
C6 C7 1.527(6) . ?
C6 H6 1.0000 . ?
C7 C8 1.520(6) . ?
C7 C11 1.543(6) . ?
C7 H7 1.0000 . ?
C8 C9 1.529(6) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.516(6) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 O1 1.467(5) . ?
C10 C15 1.499(7) . ?
C11 C12 1.518(6) . ?
C11 C13 1.543(6) . ?
C11 H11 1.0000 . ?
C12 O3 1.203(5) . ?
C12 O2 1.356(5) . ?
C13 C16 1.547(6) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 C17' 1.526(6) . ?
C16 C17 1.535(6) . ?
C16 C13' 1.551(6) . ?
C17 O5 1.200(5) . ?
C17 O4 1.350(5) . ?
C18 O4 1.468(5) . ?
C18 C19 1.479(7) . ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
C1' O1' 1.459(5) . ?
C1' C10' 1.479(6) . ?
C1' C2' 1.519(6) . ?
C1' C5' 1.547(6) . ?
C2' C3' 1.507(6) . ?
C2' H2'1 0.9900 . ?
C2' H2'2 0.9900 . ?
C3' C4' 1.329(6) . ?
C3' H3' 0.9500 . ?
C4' C14' 1.496(6) . ?
C4' C5' 1.521(6) . ?
C5' C6' 1.519(6) . ?
C5' H5' 1.0000 . ?
C6' O2' 1.457(5) . ?
C6' C7' 1.514(6) . ?
C6' H6' 1.0000 . ?
C7' C8' 1.511(6) . ?
C7' C11' 1.534(6) . ?
C7' H7' 1.0000 . ?
C8' C9' 1.525(6) . ?
C8' H8'1 0.9900 . ?
C8' H8'2 0.9900 . ?
C9' C10' 1.521(6) . ?
C9' H9'1 0.9900 . ?
C9' H9'2 0.9900 . ?
C10' O1' 1.457(5) . ?
C10' C15' 1.522(6) . ?
C11' C12' 1.525(6) . ?
C11' C13' 1.523(6) . ?
C11' H11' 1.0000 . ?
C12' O3' 1.199(5) . ?
C12' O2' 1.353(5) . ?
C13' H13C 0.9900 . ?
C13' H13D 0.9900 . ?
C14' H14D 0.9800 . ?
C14' H14E 0.9800 . ?
C14' H14F 0.9800 . ?
C15' H15D 0.9800 . ?
C15' H15E 0.9800 . ?
C15' H15F 0.9800 . ?
C17' O5' 1.205(5) . ?
C17' O4' 1.343(5) . ?
C18' O4' 1.460(5) . ?
C18' C19' 1.492(7) . ?
C18' H18C 0.9900 . ?
C18' H18D 0.9900 . ?
C19' H19D 0.9800 . ?
C19' H19E 0.9800 . ?
C19' H19F 0.9800 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 C10 59.8(3) . . ?
O1 C1 C2 115.0(4) . . ?
C10 C1 C2 123.5(4) . . ?
O1 C1 C5 117.0(3) . . ?
C10 C1 C5 125.6(4) . . ?
C2 C1 C5 107.0(4) . . ?
C3 C2 C1 102.8(4) . . ?
C3 C2 H2A 111.2 . . ?
C1 C2 H2A 111.2 . . ?
C3 C2 H2B 111.2 . . ?
C1 C2 H2B 111.2 . . ?
H2A C2 H2B 109.1 . . ?
C4 C3 C2 113.6(5) . . ?
C4 C3 H3 123.2 . . ?
C2 C3 H3 123.2 . . ?
C3 C4 C14 125.4(5) . . ?
C3 C4 C5 110.6(5) . . ?
C14 C4 C5 123.7(4) . . ?
C1 C5 C6 112.0(4) . . ?
C1 C5 C4 102.4(4) . . ?
C6 C5 C4 118.3(4) . . ?
C1 C5 H5 107.9 . . ?
C6 C5 H5 107.9 . . ?
C4 C5 H5 107.9 . . ?
O2 C6 C7 103.1(3) . . ?
O2 C6 C5 110.2(4) . . ?
C7 C6 C5 114.4(4) . . ?
O2 C6 H6 109.7 . . ?
C7 C6 H6 109.7 . . ?
C5 C6 H6 109.7 . . ?
C8 C7 C6 114.8(4) . . ?
C8 C7 C11 116.7(4) . . ?
C6 C7 C11 100.3(4) . . ?
C8 C7 H7 108.2 . . ?
C6 C7 H7 108.2 . . ?
C11 C7 H7 108.2 . . ?
C7 C8 C9 114.5(4) . . ?
C7 C8 H8A 108.6 . . ?
C9 C8 H8A 108.6 . . ?
C7 C8 H8B 108.6 . . ?
C9 C8 H8B 108.6 . . ?
H8A C8 H8B 107.6 . . ?
C10 C9 C8 117.5(4) . . ?
C10 C9 H9A 107.9 . . ?
C8 C9 H9A 107.9 . . ?
C10 C9 H9B 107.9 . . ?
C8 C9 H9B 107.9 . . ?
H9A C9 H9B 107.2 . . ?
O1 C10 C1 59.8(3) . . ?
O1 C10 C15 115.1(4) . . ?
C1 C10 C15 119.2(4) . . ?
O1 C10 C9 115.2(4) . . ?
C1 C10 C9 122.6(4) . . ?
C15 C10 C9 113.4(4) . . ?
C12 C11 C13 112.2(4) . . ?
C12 C11 C7 100.9(4) . . ?
C13 C11 C7 117.8(4) . . ?
C12 C11 H11 108.5 . . ?
C13 C11 H11 108.5 . . ?
C7 C11 H11 108.5 . . ?
O3 C12 O2 121.7(4) . . ?
O3 C12 C11 128.4(4) . . ?
O2 C12 C11 109.8(4) . . ?
C11 C13 C16 114.9(4) . . ?
C11 C13 H13A 108.5 . . ?
C16 C13 H13A 108.5 . . ?
C11 C13 H13B 108.5 . . ?
C16 C13 H13B 108.5 . . ?
H13A C13 H13B 107.5 . . ?
C4 C14 H14A 109.5 . . ?
C4 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C4 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C10 C15 H15A 109.5 . . ?
C10 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
C10 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17' C16 C17 107.8(4) . . ?
C17' C16 C13 108.4(4) . . ?
C17 C16 C13 112.7(4) . . ?
C17' C16 C13' 111.2(4) . . ?
C17 C16 C13' 107.6(3) . . ?
C13 C16 C13' 109.1(3) . . ?
O5 C17 O4 124.5(4) . . ?
O5 C17 C16 124.4(4) . . ?
O4 C17 C16 111.1(4) . . ?
O4 C18 C19 111.5(4) . . ?
O4 C18 H18A 109.3 . . ?
C19 C18 H18A 109.3 . . ?
O4 C18 H18B 109.3 . . ?
C19 C18 H18B 109.3 . . ?
H18A C18 H18B 108.0 . . ?
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 . . ?
O1' C1' C10' 59.5(3) . . ?
O1' C1' C2' 114.4(3) . . ?
C10' C1' C2' 122.9(4) . . ?
O1' C1' C5' 115.4(3) . . ?
C10' C1' C5' 127.1(4) . . ?
C2' C1' C5' 107.3(3) . . ?
C3' C2' C1' 101.6(3) . . ?
C3' C2' H2'1 111.4 . . ?
C1' C2' H2'1 111.4 . . ?
C3' C2' H2'2 111.4 . . ?
C1' C2' H2'2 111.4 . . ?
H2'1 C2' H2'2 109.3 . . ?
C4' C3' C2' 113.5(4) . . ?
C4' C3' H3' 123.3 . . ?
C2' C3' H3' 123.3 . . ?
C3' C4' C14' 125.6(4) . . ?
C3' C4' C5' 110.8(4) . . ?
C14' C4' C5' 123.3(4) . . ?
C6' C5' C4' 117.9(4) . . ?
C6' C5' C1' 113.1(3) . . ?
C4' C5' C1' 101.5(3) . . ?
C6' C5' H5' 107.9 . . ?
C4' C5' H5' 107.9 . . ?
C1' C5' H5' 107.9 . . ?
O2' C6' C7' 104.0(3) . . ?
O2' C6' C5' 109.4(3) . . ?
C7' C6' C5' 115.3(4) . . ?
O2' C6' H6' 109.3 . . ?
C7' C6' H6' 109.3 . . ?
C5' C6' H6' 109.3 . . ?
C8' C7' C6' 116.4(4) . . ?
C8' C7' C11' 114.9(4) . . ?
C6' C7' C11' 100.1(3) . . ?
C8' C7' H7' 108.3 . . ?
C6' C7' H7' 108.3 . . ?
C11' C7' H7' 108.3 . . ?
C7' C8' C9' 113.8(4) . . ?
C7' C8' H8'1 108.8 . . ?
C9' C8' H8'1 108.8 . . ?
C7' C8' H8'2 108.8 . . ?
C9' C8' H8'2 108.8 . . ?
H8'1 C8' H8'2 107.7 . . ?
C10' C9' C8' 118.0(4) . . ?
C10' C9' H9'1 107.8 . . ?
C8' C9' H9'1 107.8 . . ?
C10' C9' H9'2 107.8 . . ?
C8' C9' H9'2 107.8 . . ?
H9'1 C9' H9'2 107.1 . . ?
O1' C10' C1' 59.6(3) . . ?
O1' C10' C15' 114.2(4) . . ?
C1' C10' C15' 118.5(4) . . ?
O1' C10' C9' 115.5(4) . . ?
C1' C10' C9' 123.1(4) . . ?
C15' C10' C9' 114.0(4) . . ?
C12' C11' C13' 112.8(4) . . ?
C12' C11' C7' 100.1(3) . . ?
C13' C11' C7' 117.2(4) . . ?
C12' C11' H11' 108.7 . . ?
C13' C11' H11' 108.7 . . ?
C7' C11' H11' 108.7 . . ?
O3' C12' O2' 121.5(4) . . ?
O3' C12' C11' 128.9(4) . . ?
O2' C12' C11' 109.5(4) . . ?
C11' C13' C16 114.7(4) . . ?
C11' C13' H13C 108.6 . . ?
C16 C13' H13C 108.6 . . ?
C11' C13' H13D 108.6 . . ?
C16 C13' H13D 108.6 . . ?
H13C C13' H13D 107.6 . . ?
C4' C14' H14D 109.5 . . ?
C4' C14' H14E 109.5 . . ?
H14D C14' H14E 109.5 . . ?
C4' C14' H14F 109.5 . . ?
H14D C14' H14F 109.5 . . ?
H14E C14' H14F 109.5 . . ?
C10' C15' H15D 109.5 . . ?
C10' C15' H15E 109.5 . . ?
H15D C15' H15E 109.5 . . ?
C10' C15' H15F 109.5 . . ?
H15D C15' H15F 109.5 . . ?
H15E C15' H15F 109.5 . . ?
O5' C17' O4' 124.1(4) . . ?
O5' C17' C16 123.8(4) . . ?
O4' C17' C16 112.0(4) . . ?
O4' C18' C19' 107.7(4) . . ?
O4' C18' H18C 110.2 . . ?
C19' C18' H18C 110.2 . . ?
O4' C18' H18D 110.2 . . ?
C19' C18' H18D 110.2 . . ?
H18C C18' H18D 108.5 . . ?
C18' C19' H19D 109.5 . . ?
C18' C19' H19E 109.5 . . ?
H19D C19' H19E 109.5 . . ?
C18' C19' H19F 109.5 . . ?
H19D C19' H19F 109.5 . . ?
H19E C19' H19F 109.5 . . ?
C1 O1 C10 60.4(3) . . ?
C12 O2 C6 109.4(3) . . ?
C17 O4 C18 115.7(4) . . ?
C10' O1' C1' 60.9(3) . . ?
C12' O2' C6' 109.0(3) . . ?
C17' O4' C18' 114.7(3) . . ?

_refine_diff_density_max         0.467
_refine_diff_density_min         -0.461
_refine_diff_density_rms         0.124

####################################################################### 
# 
# 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_sal10
_database_code_depnum_ccdc_archive 'CCDC 1914346'
loop_
_audit_author_name
_audit_author_address
'Daut Islamov'
;IOPC
Russia
;
_audit_update_record             
;
2019-05-07 deposited with the CCDC.	2019-07-10 downloaded from the CCDC.
;

_audit_creation_date             2019-05-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            
3-((Diphenylphosphoryl)methyl)dihydrofuran-2(3H)-one
_chemical_formula_moiety         'C17 H17 O3 P'
_chemical_formula_sum            'C17 H17 O3 P'
_chemical_formula_weight         300.27
_chemical_melting_point          ?
_exptl_crystal_description       plate
_exptl_crystal_colour            'clear colourless'
_diffrn_ambient_temperature      100.01(10)
_chemical_oxdiff_formula         'C17 H17 O3 P'
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'
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'

_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.
;
_space_group_crystal_system      orthorhombic
_space_group_IT_number           61
_space_group_name_H-M_alt        'P b c a'
_space_group_name_Hall           '-P 2ac 2ab'
_chemical_absolute_configuration ?
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'

_cell_length_a                   8.88520(10)
_cell_length_b                   10.66490(10)
_cell_length_c                   31.4503(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2980.22(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    28988
_cell_measurement_temperature    100.01(10)
_cell_measurement_theta_max      76.3620
_cell_measurement_theta_min      2.8200
_shelx_estimated_absorpt_T_max   0.847
_shelx_estimated_absorpt_T_min   0.550
_exptl_absorpt_coefficient_mu    1.700
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.36596
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.43a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_density_diffrn    1.338
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             1264
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.279
_exptl_crystal_size_min          0.101
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0658
_diffrn_reflns_av_unetI/netI     0.0238
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       37
_diffrn_reflns_limit_l_min       -39
_diffrn_reflns_number            48852
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.638
_diffrn_reflns_theta_min         2.810
_diffrn_ambient_environment      N~2~
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -82.00  -3.00   0.50    0.05    --  -47.57 102.00-154.00  158
  2  ω    -16.00  64.00   0.50    0.05    --   47.57-102.00 101.00  160
  3  ω    -84.00 -58.00   0.50    0.09    -- -105.86 102.00-154.00   52
  4  ω   -149.00-124.00   0.50    0.09    -- -105.86-102.00 101.00   50
  5  ω    106.00 131.00   0.50    0.09    --  105.86 102.00-154.00   50
  6  ω     35.00 110.00   0.50    0.09    --  105.86-102.00 101.00  150
  7  ω     42.00 119.00   0.50    0.05    --   47.57  77.00 120.00  154
  8  ω     26.00  58.00   0.50    0.05    --   47.57  77.00-180.00   64
  9  ω     41.00  66.00   0.50    0.05    --   47.57  57.00-180.00   50
 10  ω     73.00 117.00   0.50    0.05    --   47.57 125.00 -90.00   88
 11  ω     83.00 111.00   0.50    0.05    --   47.57  57.00-180.00   56
 12  ω     27.00  89.00   0.50    0.05    --   47.57  77.00  90.00  124
 13  ω     72.00 116.00   0.50    0.05    --   47.57 125.00  90.00   88
 14  ω     35.00 114.00   0.50    0.05    --   47.57  37.00  90.00  158
 15  ω   -164.00-138.00   0.50    0.09    -- -105.86 -59.00  75.04   52
 16  ω   -115.00 -89.00   0.50    0.09    -- -105.86 -68.00  93.33   52
 17  ω   -147.00 -94.00   0.50    0.09    -- -105.86 -42.00 151.20  106
 18  ω   -119.00 -94.00   0.50    0.09    -- -105.86 -50.00  95.73   50
 19  ω   -103.00 -78.00   0.50    0.09    -- -105.86 -88.00  98.93   50
 20  ω   -104.00 -78.00   0.50    0.09    -- -105.86 -91.00 101.02   52
 21  ω   -117.00 -91.00   0.50    0.09    -- -105.86 -63.00  59.88   52
 22  ω   -105.00 -80.00   0.50    0.09    -- -105.86 -83.00 135.10   50
 23  ω   -172.00 -93.00   0.50    0.09    -- -105.86 -45.00 178.62  158
 24  ω   -142.00 -93.00   0.50    0.09    -- -105.86 -45.00  60.00   98
 25  ω   -113.00 -88.00   0.50    0.09    -- -105.86 -65.00 170.10   50
 26  ω   -111.00 -86.00   0.50    0.09    -- -105.86 -69.00-169.93   50
 27  ω   -110.00 -85.00   0.50    0.09    -- -105.86 -72.00 107.99   50
 28  ω   -108.00 -83.00   0.50    0.09    -- -105.86 -77.00 139.69   50
 29  ω   -103.00 -78.00   0.50    0.09    -- -105.86 -88.00 174.18   50
 30  ω   -175.00 -94.00   0.50    0.09    -- -105.86 -30.00 120.00  162
 31  ω   -114.00 -89.00   0.50    0.09    -- -105.86 -64.00 157.64   50
 32  ω   -129.00-103.00   0.50    0.09    -- -105.86 -61.00 120.00   52
 33  ω   -108.00 -83.00   0.50    0.09    -- -105.86 -77.00  90.00   50
 34  ω   -108.00 -83.00   0.50    0.09    -- -105.86 -77.00 150.00   50
 35  ω   -115.00 -90.00   0.50    0.09    -- -105.86 -59.00  75.04   50
 36  ω   -114.00 -89.00   0.50    0.09    -- -105.86 -61.00  90.00   50
 37  ω   -116.00 -91.00   0.50    0.09    -- -105.86 -61.00  60.00   50
 38  ω   -105.00 -80.00   0.50    0.09    -- -105.86 -83.00 164.69   50
 39  ω   -104.00 -79.00   0.50    0.09    -- -105.86 -87.00 179.79   50
 40  ω   -111.00 -86.00   0.50    0.09    -- -105.86 -70.00-163.23   50
 41  ω   -103.00 -78.00   0.50    0.09    -- -105.86 -88.00-159.81   50
 42  ω   -119.00 -94.00   0.50    0.09    -- -105.86 -49.00  68.72   50
 43  ω   -168.00-142.00   0.50    0.09    -- -105.86 -70.00-163.23   52
 44  ω   -105.00 -80.00   0.50    0.09    -- -105.86 -83.00 166.41   50
 45  ω   -103.00 -78.00   0.50    0.09    -- -105.86 -89.00-176.85   50
 46  ω   -109.00 -84.00   0.50    0.09    -- -105.86 -77.00-180.00   50
 47  ω   -174.00 -95.00   0.50    0.09    -- -105.86 -48.00  50.69  158
 48  ω   -146.00 -92.00   0.50    0.09    -- -105.86 -51.00  91.92  108
 49  ω   -110.00 -85.00   0.50    0.09    -- -105.86 -73.00-175.39   50
 50  ω     33.00 128.00   0.50    0.09    --  105.86 -77.00-180.00  190
 51  ω     83.00 108.00   0.50    0.09    --  105.86  77.00  60.00   50
 52  ω    153.00 178.00   0.50    0.09    --  105.86  77.00 150.00   50
 53  ω     83.00 109.00   0.50    0.09    --  105.86  77.00 150.00   52
 54  ω    152.00 178.00   0.50    0.09    --  105.86  77.00 120.00   52
 55  ω     90.00 116.00   0.50    0.09    --  105.86  61.00  90.00   52
 56  ω     83.00 109.00   0.50    0.09    --  105.86  77.00 120.00   52
 57  ω     31.00 117.00   0.50    0.09    --  105.86 -30.00  90.00  172
 58  ω     36.00 108.00   0.50    0.09    --  105.86 -45.00  60.00  144
 59  ω    142.00 167.00   0.50    0.09    --  105.86  77.00  90.00   50
 60  ω     84.00 110.00   0.50    0.09    --  105.86  77.00  90.00   52
 61  ω    141.00 166.00   0.50    0.09    --  105.86  77.00  60.00   50
 62  ω    106.00 178.00   0.50    0.09    --  105.86  45.00 -60.00  144
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0854025000
_diffrn_orient_matrix_UB_12      -0.0228381000
_diffrn_orient_matrix_UB_13      -0.0419246000
_diffrn_orient_matrix_UB_21      -0.1466791000
_diffrn_orient_matrix_UB_22      0.0460053000
_diffrn_orient_matrix_UB_23      0.0209499000
_diffrn_orient_matrix_UB_31      0.0355549000
_diffrn_orient_matrix_UB_32      0.1349835000
_diffrn_orient_matrix_UB_33      -0.0142466000
_diffrn_oxdiff_digest_frames     
;
011a994f68e95db14fabe698ac64114fc5000667d56
;
_diffrn_oxdiff_digest_hkl        
;
01116d7f5ebeee673d6e338c8adaeae6a48b33
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2901
_reflns_number_total             3118
_reflns_odcompleteness_completeness 99.97
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.43a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.43a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.43a (Rigaku OD, 2019)'
_computing_molecular_graphics    'MERCURY 4.1 (Macrae, 2006)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.428
_refine_diff_density_min         -0.951
_refine_diff_density_rms         0.103
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.145
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         3118
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0654
_refine_ls_R_factor_gt           0.0546
_refine_ls_restrained_S_all      1.145
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0694P)²+2.8679P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1295
_refine_ls_wR_factor_ref         0.1438
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Ternary CH refined with riding coordinates:
 C14(H14)
2.b Secondary CH2 refined with riding coordinates:
 C13(H13A,H13B), C16(H16A,H16B), C17(H17A,H17B)
2.c Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C6(H6), C8(H8), C9(H9), C10(H10), C11(H11),
 C12(H12)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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 0.69076(5) 0.25818(4) 0.37266(2) 0.01725(17) Uani 1 1 d . . . . .
O1 O 0.64938(17) 0.12572(12) 0.38205(4) 0.0251(3) Uani 1 1 d . . . . .
O2 O 1.02234(18) 0.28096(16) 0.48257(5) 0.0363(4) Uani 1 1 d . . . . .
O3 O 0.87328(17) 0.41125(14) 0.51869(4) 0.0292(3) Uani 1 1 d . . . . .
C1 C 0.7712(2) 0.27532(18) 0.32022(6) 0.0229(4) Uani 1 1 d . . . . .
C2 C 0.8739(3) 0.3671(2) 0.30863(8) 0.0410(6) Uani 1 1 d . . . . .
H2 H 0.9095 0.4250 0.3293 0.049 Uiso 1 1 calc R . . . .
C3 C 0.9251(4) 0.3749(3) 0.26676(8) 0.0498(7) Uani 1 1 d . . . . .
H3 H 0.9963 0.4373 0.2591 0.060 Uiso 1 1 calc R . . . .
C4 C 0.8727(3) 0.2925(3) 0.23664(7) 0.0441(6) Uani 1 1 d . . . . .
H4 H 0.9038 0.3009 0.2079 0.053 Uiso 1 1 calc R . . . .
C5 C 0.7758(3) 0.1985(3) 0.24789(7) 0.0442(6) Uani 1 1 d . . . . .
H5 H 0.7439 0.1391 0.2273 0.053 Uiso 1 1 calc R . . . .
C6 C 0.7239(3) 0.1901(2) 0.28968(7) 0.0348(5) Uani 1 1 d . . . . .
H6 H 0.6556 0.1253 0.2973 0.042 Uiso 1 1 calc R . . . .
C7 C 0.5253(2) 0.35661(17) 0.37343(5) 0.0175(4) Uani 1 1 d . . . . .
C8 C 0.5228(2) 0.47691(17) 0.35590(6) 0.0232(4) Uani 1 1 d . . . . .
H8 H 0.6121 0.5125 0.3445 0.028 Uiso 1 1 calc R . . . .
C9 C 0.3883(3) 0.5446(2) 0.35522(7) 0.0309(5) Uani 1 1 d . . . . .
H9 H 0.3863 0.6267 0.3435 0.037 Uiso 1 1 calc R . . . .
C10 C 0.2580(3) 0.4925(2) 0.37164(8) 0.0352(6) Uani 1 1 d . . . . .
H10 H 0.1660 0.5379 0.3703 0.042 Uiso 1 1 calc R . . . .
C11 C 0.2612(2) 0.3746(2) 0.38999(7) 0.0341(5) Uani 1 1 d . . . . .
H11 H 0.1720 0.3398 0.4017 0.041 Uiso 1 1 calc R . . . .
C12 C 0.3950(2) 0.30687(18) 0.39122(6) 0.0244(4) Uani 1 1 d . . . . .
H12 H 0.3973 0.2265 0.4042 0.029 Uiso 1 1 calc R . . . .
C13 C 0.8286(2) 0.32327(18) 0.40867(6) 0.0203(4) Uani 1 1 d . . . . .
H13A H 0.9199 0.2701 0.4080 0.024 Uiso 1 1 calc R . . . .
H13B H 0.8573 0.4078 0.3985 0.024 Uiso 1 1 calc R . . . .
C14 C 0.7735(2) 0.33346(17) 0.45449(6) 0.0193(4) Uani 1 1 d . . . . .
H14 H 0.7095 0.2588 0.4611 0.023 Uiso 1 1 calc R . . . .
C15 C 0.9051(2) 0.33689(19) 0.48540(6) 0.0246(4) Uani 1 1 d . . . . .
C16 C 0.6868(2) 0.45222(19) 0.46626(6) 0.0238(4) Uani 1 1 d . . . . .
H16A H 0.7206 0.5247 0.4491 0.029 Uiso 1 1 calc R . . . .
H16B H 0.5771 0.4406 0.4623 0.029 Uiso 1 1 calc R . . . .
C17 C 0.7262(2) 0.4697(2) 0.51314(6) 0.0275(4) Uani 1 1 d . . . . .
H17A H 0.7305 0.5599 0.5205 0.033 Uiso 1 1 calc R . . . .
H17B H 0.6502 0.4286 0.5315 0.033 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 O1 1.4893(14) . ?
P1 C1 1.8067(19) . ?
P1 C7 1.8066(19) . ?
P1 C13 1.807(2) . ?
O2 C15 1.204(3) . ?
O3 C15 1.344(2) . ?
O3 C17 1.458(3) . ?
C1 C2 1.387(3) . ?
C1 C6 1.388(3) . ?
C2 H2 0.9500 . ?
C2 C3 1.396(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.373(4) . ?
C4 H4 0.9500 . ?
C4 C5 1.368(4) . ?
C5 H5 0.9500 . ?
C5 C6 1.396(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.397(3) . ?
C7 C12 1.391(3) . ?
C8 H8 0.9500 . ?
C8 C9 1.396(3) . ?
C9 H9 0.9500 . ?
C9 C10 1.384(3) . ?
C10 H10 0.9500 . ?
C10 C11 1.384(4) . ?
C11 H11 0.9500 . ?
C11 C12 1.391(3) . ?
C12 H12 0.9500 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.526(2) . ?
C14 H14 1.0000 . ?
C14 C15 1.521(3) . ?
C14 C16 1.528(3) . ?
C16 H16A 0.9900 . ?
C16 H16B 0.9900 . ?
C16 C17 1.527(3) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?

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 C1 112.00(9) . . ?
O1 P1 C7 110.34(9) . . ?
O1 P1 C13 114.05(9) . . ?
C7 P1 C1 105.99(8) . . ?
C7 P1 C13 108.66(8) . . ?
C13 P1 C1 105.37(9) . . ?
C15 O3 C17 110.33(15) . . ?
C2 C1 P1 124.87(16) . . ?
C2 C1 C6 118.66(19) . . ?
C6 C1 P1 116.46(16) . . ?
C1 C2 H2 119.8 . . ?
C1 C2 C3 120.3(2) . . ?
C3 C2 H2 119.8 . . ?
C2 C3 H3 119.9 . . ?
C4 C3 C2 120.1(3) . . ?
C4 C3 H3 119.9 . . ?
C3 C4 H4 119.9 . . ?
C5 C4 C3 120.3(2) . . ?
C5 C4 H4 119.9 . . ?
C4 C5 H5 120.0 . . ?
C4 C5 C6 119.9(2) . . ?
C6 C5 H5 120.0 . . ?
C1 C6 C5 120.6(2) . . ?
C1 C6 H6 119.7 . . ?
C5 C6 H6 119.7 . . ?
C8 C7 P1 122.79(15) . . ?
C12 C7 P1 117.46(14) . . ?
C12 C7 C8 119.72(18) . . ?
C7 C8 H8 120.2 . . ?
C9 C8 C7 119.66(19) . . ?
C9 C8 H8 120.2 . . ?
C8 C9 H9 119.9 . . ?
C10 C9 C8 120.2(2) . . ?
C10 C9 H9 119.9 . . ?
C9 C10 H10 119.9 . . ?
C9 C10 C11 120.2(2) . . ?
C11 C10 H10 119.9 . . ?
C10 C11 H11 120.0 . . ?
C10 C11 C12 120.1(2) . . ?
C12 C11 H11 120.0 . . ?
C7 C12 H12 119.9 . . ?
C11 C12 C7 120.14(19) . . ?
C11 C12 H12 119.9 . . ?
P1 C13 H13A 108.8 . . ?
P1 C13 H13B 108.8 . . ?
H13A C13 H13B 107.7 . . ?
C14 C13 P1 113.70(13) . . ?
C14 C13 H13A 108.8 . . ?
C14 C13 H13B 108.8 . . ?
C13 C14 H14 108.8 . . ?
C13 C14 C16 116.72(15) . . ?
C15 C14 C13 111.00(15) . . ?
C15 C14 H14 108.8 . . ?
C15 C14 C16 102.29(15) . . ?
C16 C14 H14 108.8 . . ?
O2 C15 O3 122.15(18) . . ?
O2 C15 C14 127.33(18) . . ?
O3 C15 C14 110.51(16) . . ?
C14 C16 H16A 111.2 . . ?
C14 C16 H16B 111.2 . . ?
H16A C16 H16B 109.1 . . ?
C17 C16 C14 102.68(15) . . ?
C17 C16 H16A 111.2 . . ?
C17 C16 H16B 111.2 . . ?
O3 C17 C16 105.60(15) . . ?
O3 C17 H17A 110.6 . . ?
O3 C17 H17B 110.6 . . ?
C16 C17 H17A 110.6 . . ?
C16 C17 H17B 110.6 . . ?
H17A C17 H17B 108.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
P1 C1 C2 C3 -177.7(2) . . . . ?
P1 C1 C6 C5 177.75(19) . . . . ?
P1 C7 C8 C9 175.94(14) . . . . ?
P1 C7 C12 C11 -175.36(15) . . . . ?
P1 C13 C14 C15 157.00(13) . . . . ?
P1 C13 C14 C16 -86.36(18) . . . . ?
O1 P1 C1 C2 -151.7(2) . . . . ?
O1 P1 C1 C6 29.01(19) . . . . ?
O1 P1 C7 C8 -163.92(14) . . . . ?
O1 P1 C7 C12 14.01(17) . . . . ?
O1 P1 C13 C14 -64.29(15) . . . . ?
C1 P1 C7 C8 -42.47(17) . . . . ?
C1 P1 C7 C12 135.46(15) . . . . ?
C1 P1 C13 C14 172.47(13) . . . . ?
C1 C2 C3 C4 0.8(4) . . . . ?
C2 C1 C6 C5 -1.6(4) . . . . ?
C2 C3 C4 C5 -3.3(4) . . . . ?
C3 C4 C5 C6 3.3(4) . . . . ?
C4 C5 C6 C1 -0.9(4) . . . . ?
C6 C1 C2 C3 1.6(4) . . . . ?
C7 P1 C1 C2 87.9(2) . . . . ?
C7 P1 C1 C6 -91.38(17) . . . . ?
C7 P1 C13 C14 59.24(15) . . . . ?
C7 C8 C9 C10 -0.4(3) . . . . ?
C8 C7 C12 C11 2.6(3) . . . . ?
C8 C9 C10 C11 2.0(3) . . . . ?
C9 C10 C11 C12 -1.3(3) . . . . ?
C10 C11 C12 C7 -1.0(3) . . . . ?
C12 C7 C8 C9 -2.0(3) . . . . ?
C13 P1 C1 C2 -27.2(2) . . . . ?
C13 P1 C1 C6 153.54(16) . . . . ?
C13 P1 C7 C8 70.35(16) . . . . ?
C13 P1 C7 C12 -111.72(15) . . . . ?
C13 C14 C15 O2 -36.1(3) . . . . ?
C13 C14 C15 O3 145.43(16) . . . . ?
C13 C14 C16 C17 -149.19(17) . . . . ?
C14 C16 C17 O3 27.2(2) . . . . ?
C15 O3 C17 C16 -15.6(2) . . . . ?
C15 C14 C16 C17 -27.84(19) . . . . ?
C16 C14 C15 O2 -161.3(2) . . . . ?
C16 C14 C15 O3 20.2(2) . . . . ?
C17 O3 C15 O2 178.34(19) . . . . ?
C17 O3 C15 C14 -3.1(2) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.874
_oxdiff_exptl_absorpt_empirical_full_min 0.516

####################################################################### 
# 
# 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_Sal3_a
_database_code_depnum_ccdc_archive 'CCDC 1914345'
loop_
_audit_author_name
_audit_author_address
'Daut Islamov'
;IOPC
Russia
;
_audit_update_record             
;
2019-05-07 deposited with the CCDC.	2019-07-10 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            
'Diethyl 2,2-bis((2-oxotetrahydrofuran-3-yl)methyl)malonate'
_chemical_formula_moiety         'C17 H24 O8'
_chemical_formula_sum            'C17 H24 O8'
_chemical_melting_point          ?

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_diffrn_ambient_temperature      296(2)
_chemical_formula_weight         356.36

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'
_chemical_absolute_configuration ?

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

_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.
;

_cell_length_a                   10.1251(6)
_cell_length_b                   10.1582(7)
_cell_length_c                   17.4602(11)
_cell_angle_alpha                90
_cell_angle_beta                 95.237(4)
_cell_angle_gamma                90
_cell_volume                     1788.3(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    2573
_cell_measurement_theta_min      2.95
_cell_measurement_theta_max      20.64
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.324
_exptl_crystal_F_000             760
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.333
_exptl_crystal_size_mid          0.249
_exptl_crystal_size_min          0.213
_exptl_absorpt_coefficient_mu    0.105
_shelx_estimated_absorpt_T_min   0.966
_shelx_estimated_absorpt_T_max   0.978
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6944
_exptl_absorpt_correction_T_max  0.7455
_exptl_absorpt_process_details   sadabs
_exptl_absorpt_special_details   ?
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'sealed x-ray tube'
_diffrn_measurement_device_type  'Bruker Kappa APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            20578
_diffrn_reflns_av_unetI/netI     0.0632
_diffrn_reflns_av_R_equivalents  0.0735
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.322
_diffrn_reflns_theta_max         26.098
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measured_fraction_theta_full 0.996
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_Laue_measured_fraction_full 0.996
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.996
_reflns_number_total             3531
_reflns_number_gt                1864
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

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

_computing_data_collection       'APEX2  v2, 1-4  (Bruker AXS, 2005-2007)'
_computing_cell_refinement       'APEX2  v2, 1-4  (Bruker AXS, 2005-2007)'
_computing_data_reduction        'SAINT NT v6.0 (Bruker AXS, 2003)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'MERCURY 4.1 (Macrae, 2006)'
_computing_publication_material  'enCIFer (Allen et al. 2004)'
_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)+(0.1000P)²+0.0636P] 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-2014/7 (Sheldrick 2014'
_refine_ls_extinction_coef       0.052(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         3531
_refine_ls_number_parameters     229
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1338
_refine_ls_R_factor_gt           0.0709
_refine_ls_wR_factor_ref         0.2134
_refine_ls_wR_factor_gt          0.1693
_refine_ls_goodness_of_fit_ref   1.108
_refine_ls_restrained_S_all      1.108
_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
C1 C 0.2823(3) 0.6088(3) 0.61996(15) 0.0418(8) Uani 1 1 d . . . . .
C2 C 0.3961(3) 0.6382(3) 0.68316(16) 0.0455(8) Uani 1 1 d . . . . .
H2A H 0.3687 0.7099 0.7148 0.055 Uiso 1 1 calc R U . . .
H2B H 0.4094 0.5612 0.7158 0.055 Uiso 1 1 calc R U . . .
C3 C 0.5281(3) 0.6747(3) 0.65322(17) 0.0458(8) Uani 1 1 d . . . . .
H3 H 0.5328 0.6310 0.6035 0.055 Uiso 1 1 calc R U . . .
C4 C 0.5591(3) 0.8193(4) 0.6431(2) 0.0589(9) Uani 1 1 d . . . . .
H4A H 0.5266 0.8500 0.5922 0.071 Uiso 1 1 calc R U . . .
H4B H 0.5205 0.8727 0.6814 0.071 Uiso 1 1 calc R U . . .
C5 C 0.7082(3) 0.8229(4) 0.6542(2) 0.0691(11) Uani 1 1 d . . . . .
H5A H 0.7459 0.8097 0.6056 0.083 Uiso 1 1 calc R U . . .
H5B H 0.7391 0.9065 0.6758 0.083 Uiso 1 1 calc R U . . .
C6 C 0.6443(3) 0.6281(4) 0.7067(2) 0.0579(10) Uani 1 1 d . . . . .
C7 C 0.2497(3) 0.7246(3) 0.56546(16) 0.0470(8) Uani 1 1 d . . . . .
H7A H 0.3279 0.7450 0.5395 0.056 Uiso 1 1 calc R U . . .
H7B H 0.1808 0.6971 0.5265 0.056 Uiso 1 1 calc R U . . .
C8 C 0.2045(3) 0.8484(3) 0.60245(17) 0.0482(8) Uani 1 1 d . . . . .
H8 H 0.2653 0.8661 0.6482 0.058 Uiso 1 1 calc R U . . .
C9 C 0.0638(4) 0.8556(4) 0.6255(2) 0.0653(10) Uani 1 1 d . . . . .
H9A H 0.0025 0.8091 0.5890 0.078 Uiso 1 1 calc R U . . .
H9B H 0.0579 0.8194 0.6765 0.078 Uiso 1 1 calc R U . . .
C10 C 0.0370(4) 1.0023(4) 0.6239(2) 0.0663(10) Uani 1 1 d . . . . .
H10A H -0.0570 1.0200 0.6129 0.080 Uiso 1 1 calc R U . . .
H10B H 0.0677 1.0426 0.6727 0.080 Uiso 1 1 calc R U . . .
C11 C 0.2073(4) 0.9645(3) 0.5497(2) 0.0549(9) Uani 1 1 d . . . . .
C12 C 0.3225(3) 0.4904(4) 0.5738(2) 0.0511(9) Uani 1 1 d . . . . .
C13 C 0.3850(5) 0.2631(4) 0.5874(3) 0.1097(18) Uani 1 1 d . . . . .
H13A H 0.3338 0.1914 0.6064 0.132 Uiso 1 1 calc R U . . .
H13B H 0.3669 0.2658 0.5319 0.132 Uiso 1 1 calc R U . . .
C14 C 0.5191(5) 0.2379(6) 0.6056(3) 0.117(2) Uani 1 1 d . . . . .
H14A H 0.5705 0.2927 0.5747 0.175 Uiso 1 1 calc R U . . .
H14B H 0.5371 0.1471 0.5956 0.175 Uiso 1 1 calc R U . . .
H14C H 0.5423 0.2567 0.6590 0.175 Uiso 1 1 calc R U . . .
C15 C 0.1598(3) 0.5673(3) 0.6589(2) 0.0485(8) Uani 1 1 d . . . . .
C16 C -0.0577(3) 0.4779(4) 0.6319(2) 0.0662(11) Uani 1 1 d . . . . .
H16A H -0.1312 0.4959 0.5937 0.079 Uiso 1 1 calc R U . . .
H16B H -0.0751 0.5217 0.6793 0.079 Uiso 1 1 calc R U . . .
C17 C -0.0466(4) 0.3338(5) 0.6452(3) 0.0892(13) Uani 1 1 d . . . . .
H17A H -0.0191 0.2918 0.6001 0.134 Uiso 1 1 calc R U . . .
H17B H -0.1312 0.2995 0.6562 0.134 Uiso 1 1 calc R U . . .
H17C H 0.0176 0.3171 0.6881 0.134 Uiso 1 1 calc R U . . .
O1 O 0.7447(2) 0.7159(3) 0.70694(14) 0.0718(8) Uani 1 1 d . . . . .
O2 O 0.6551(3) 0.5310(3) 0.74492(17) 0.0851(9) Uani 1 1 d . . . . .
O3 O 0.1110(2) 1.0507(2) 0.56295(14) 0.0633(7) Uani 1 1 d . . . . .
O4 O 0.2810(3) 0.9847(3) 0.50121(16) 0.0825(9) Uani 1 1 d . . . . .
O5 O 0.3419(3) 0.3861(3) 0.61955(14) 0.0756(8) Uani 1 1 d . . . . .
O6 O 0.3343(2) 0.4898(3) 0.50636(14) 0.0674(8) Uani 1 1 d . . . . .
O7 O 0.0645(2) 0.5286(2) 0.60531(12) 0.0575(7) Uani 1 1 d . . . . .
O8 O 0.1489(2) 0.5700(3) 0.72628(13) 0.0607(7) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C12 1.524(5) . ?
C1 C15 1.528(4) . ?
C1 C7 1.530(4) . ?
C1 C2 1.550(4) . ?
C2 C3 1.525(4) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C6 1.510(4) . ?
C3 C4 1.516(5) . ?
C3 H3 0.9800 . ?
C4 C5 1.505(5) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 O1 1.450(5) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 O2 1.191(4) . ?
C6 O1 1.352(4) . ?
C7 C8 1.504(4) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C11 1.499(5) . ?
C8 C9 1.516(4) . ?
C8 H8 0.9800 . ?
C9 C10 1.515(5) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 O3 1.443(4) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 O4 1.196(4) . ?
C11 O3 1.347(4) . ?
C12 O6 1.194(4) . ?
C12 O5 1.331(4) . ?
C13 C14 1.390(6) . ?
C13 O5 1.453(5) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 O8 1.192(3) . ?
C15 O7 1.340(4) . ?
C16 O7 1.454(4) . ?
C16 C17 1.484(6) . ?
C16 H16A 0.9700 . ?
C16 H16B 0.9700 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 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
C12 C1 C15 106.5(3) . . ?
C12 C1 C7 109.3(2) . . ?
C15 C1 C7 110.5(2) . . ?
C12 C1 C2 108.2(2) . . ?
C15 C1 C2 108.5(2) . . ?
C7 C1 C2 113.5(3) . . ?
C3 C2 C1 114.9(2) . . ?
C3 C2 H2A 108.5 . . ?
C1 C2 H2A 108.5 . . ?
C3 C2 H2B 108.5 . . ?
C1 C2 H2B 108.5 . . ?
H2A C2 H2B 107.5 . . ?
C6 C3 C4 102.6(3) . . ?
C6 C3 C2 111.7(3) . . ?
C4 C3 C2 118.2(3) . . ?
C6 C3 H3 108.0 . . ?
C4 C3 H3 108.0 . . ?
C2 C3 H3 108.0 . . ?
C5 C4 C3 102.9(3) . . ?
C5 C4 H4A 111.2 . . ?
C3 C4 H4A 111.2 . . ?
C5 C4 H4B 111.2 . . ?
C3 C4 H4B 111.2 . . ?
H4A C4 H4B 109.1 . . ?
O1 C5 C4 104.9(3) . . ?
O1 C5 H5A 110.8 . . ?
C4 C5 H5A 110.8 . . ?
O1 C5 H5B 110.8 . . ?
C4 C5 H5B 110.8 . . ?
H5A C5 H5B 108.8 . . ?
O2 C6 O1 121.0(3) . . ?
O2 C6 C3 129.2(3) . . ?
O1 C6 C3 109.8(3) . . ?
C8 C7 C1 115.6(2) . . ?
C8 C7 H7A 108.4 . . ?
C1 C7 H7A 108.4 . . ?
C8 C7 H7B 108.4 . . ?
C1 C7 H7B 108.4 . . ?
H7A C7 H7B 107.4 . . ?
C11 C8 C7 111.7(3) . . ?
C11 C8 C9 101.3(3) . . ?
C7 C8 C9 119.0(3) . . ?
C11 C8 H8 108.1 . . ?
C7 C8 H8 108.1 . . ?
C9 C8 H8 108.1 . . ?
C10 C9 C8 102.3(3) . . ?
C10 C9 H9A 111.3 . . ?
C8 C9 H9A 111.3 . . ?
C10 C9 H9B 111.3 . . ?
C8 C9 H9B 111.3 . . ?
H9A C9 H9B 109.2 . . ?
O3 C10 C9 104.2(3) . . ?
O3 C10 H10A 110.9 . . ?
C9 C10 H10A 110.9 . . ?
O3 C10 H10B 110.9 . . ?
C9 C10 H10B 110.9 . . ?
H10A C10 H10B 108.9 . . ?
O4 C11 O3 121.2(3) . . ?
O4 C11 C8 128.2(3) . . ?
O3 C11 C8 110.5(3) . . ?
O6 C12 O5 124.4(3) . . ?
O6 C12 C1 125.5(3) . . ?
O5 C12 C1 110.0(3) . . ?
C14 C13 O5 113.0(4) . . ?
C14 C13 H13A 109.0 . . ?
O5 C13 H13A 109.0 . . ?
C14 C13 H13B 109.0 . . ?
O5 C13 H13B 109.0 . . ?
H13A C13 H13B 107.8 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O8 C15 O7 124.8(3) . . ?
O8 C15 C1 125.8(3) . . ?
O7 C15 C1 109.4(3) . . ?
O7 C16 C17 110.2(3) . . ?
O7 C16 H16A 109.6 . . ?
C17 C16 H16A 109.6 . . ?
O7 C16 H16B 109.6 . . ?
C17 C16 H16B 109.6 . . ?
H16A C16 H16B 108.1 . . ?
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 . . ?
C6 O1 C5 110.1(3) . . ?
C11 O3 C10 109.8(3) . . ?
C12 O5 C13 119.0(3) . . ?
C15 O7 C16 117.4(3) . . ?

_refine_diff_density_max         0.408
_refine_diff_density_min         -0.345
_refine_diff_density_rms         0.118

####################################################################### 
# 
# 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_sal9
_database_code_depnum_ccdc_archive 'CCDC 1914344'
loop_
_audit_author_name
_audit_author_address
'Daut Islamov'
;IOPC
Russia
;
_audit_update_record             
;
2019-05-07 deposited with the CCDC.	2019-07-10 downloaded from the CCDC.
;

_audit_creation_date             2019-05-07
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            
(1R,5R,6S,7S,10S,11S)-11-((diphenylphosphoryl)methyl)-1,10-epoxyguaia-3-ene-6,12-olid
_chemical_formula_moiety         'C27 H29 O4 P'
_chemical_formula_sum            'C27 H29 O4 P'
_chemical_formula_weight         448.47
_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'
_chemical_absolute_configuration ad
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'
_chemical_melting_point          ?
_exptl_crystal_description       needle
_exptl_crystal_colour            'clear colourless'
_diffrn_ambient_temperature      100.00(10)
_chemical_oxdiff_formula         'C27 H29 O4 P1'
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'
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'

_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.
;

_cell_length_a                   6.0344(2)
_cell_length_b                   31.7014(10)
_cell_length_c                   12.0302(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2301.36(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5890
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      76.2480
_cell_measurement_theta_min      3.9290
_shelx_estimated_absorpt_T_max   0.866
_shelx_estimated_absorpt_T_min   0.801
_exptl_absorpt_coefficient_mu    1.311
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.49215
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.43a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_density_diffrn    1.294
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_F_000             952
_exptl_crystal_size_max          0.177
_exptl_crystal_size_mid          0.141
_exptl_crystal_size_min          0.113
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0513
_diffrn_reflns_av_unetI/netI     0.0507
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.972
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       30
_diffrn_reflns_limit_k_min       -39
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            11464
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.957
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.407
_diffrn_reflns_theta_min         2.788
_diffrn_ambient_environment      N~2~
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.972
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      2.00  82.00   0.50    0.16    --   47.45-103.00 152.00  160
  2  ω    -80.00 -35.00   0.50    0.62    -- -105.86 103.00-105.00   90
  3  ω   -118.00 -36.00   0.50    0.62    -- -105.86  41.00 161.00  164
  4  ω     81.00 121.00   0.50    0.62    --  105.86  88.00  -0.00   80
  5  ω   -119.00 -93.00   0.50    0.16    --  -47.45-125.00-120.00   52
  6  ω   -119.00 -71.00   0.50    0.16    --  -47.45-125.00 -60.00   96
  7  ω     16.00  95.00   0.50    0.16    --   47.45-125.00  60.00  158
  8  ω     74.00 102.00   0.50    0.16    --   47.45 125.00  30.00   56
  9  ω   -116.00 -89.00   0.50    0.62    -- -105.86  15.00 -60.00   54
 10  ω   -167.00-138.00   0.50    0.62    -- -105.86 -15.00 -90.00   58
 11  ω   -176.00 -92.00   0.50    0.62    -- -105.86 -15.00 -60.00  168
 12  ω   -131.00-105.00   0.50    0.62    -- -105.86 -15.00 -90.00   52
 13  ω     36.00 113.00   0.50    0.62    --  105.86 -45.00 150.00  154
 14  ω     46.00 107.00   0.50    0.62    --  105.86 -94.00   0.00  122
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at home/near, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.2257367000
_diffrn_orient_matrix_UB_12      0.0225229000
_diffrn_orient_matrix_UB_13      -0.0074627000
_diffrn_orient_matrix_UB_21      -0.0949501000
_diffrn_orient_matrix_UB_22      -0.0376287000
_diffrn_orient_matrix_UB_23      -0.0655259000
_diffrn_orient_matrix_UB_31      -0.0722542000
_diffrn_orient_matrix_UB_32      -0.0209380000
_diffrn_orient_matrix_UB_33      0.1097533000
_diffrn_oxdiff_digest_frames     
;
0113fd809c3e535e104f90b65a692f4400000457f39
;
_diffrn_oxdiff_digest_hkl        
;
0168adb4842fce16a0d9420149d29574591603
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_reflns_Friedel_coverage         0.697
_reflns_Friedel_fraction_full    0.995
_reflns_Friedel_fraction_max     0.935
_reflns_number_gt                4152
_reflns_number_total             4629
_reflns_odcompleteness_completeness 99.84
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     66.97
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.43a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.43a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.43a (Rigaku OD, 2019)'
_computing_molecular_graphics    'MERCURY 4.1 (Macrae, 2006)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.643
_refine_diff_density_min         -0.361
_refine_diff_density_rms         0.078
_refine_ls_abs_structure_details 
;
 Flack x determined using 1546 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.01(2)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.087
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     291
_refine_ls_number_reflns         4629
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0718
_refine_ls_R_factor_gt           0.0576
_refine_ls_restrained_S_all      1.087
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0532P)²+4.5142P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1408
_refine_ls_wR_factor_ref         0.1614
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Ternary CH refined with riding coordinates:
 C5(H5), C6(H6), C7(H7), C11(H11)
2.b Secondary CH2 refined with riding coordinates:
 C2(H2A,H2B), C8(H8A,H8B), C9(H9A,H9B), C13(H13A,H13B)
2.c Aromatic/amide H refined with riding coordinates:
 C3(H3), C17(H17), C18(H18), C19(H19), C20(H20), C21(H21), C23(H23), C24(H24),
 C25(H25), C26(H26), C27(H27)
2.d Idealised Me refined as rotating group:
 C14(H14A,H14B,H14C), C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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 0.37825(19) 0.65684(4) 0.28122(10) 0.0241(3) Uani 1 1 d . . . . .
O1 O 0.1940(6) 0.65168(13) 0.3620(3) 0.0325(8) Uani 1 1 d . . . . .
O2 O 0.8405(6) 0.60632(11) 0.7398(3) 0.0276(8) Uani 1 1 d . . . . .
O3 O 0.9619(6) 0.55009(11) 0.4276(3) 0.0288(8) Uani 1 1 d . . . . .
O4 O 0.9420(7) 0.55759(12) 0.2436(3) 0.0349(9) Uani 1 1 d . . . . .
C1 C 0.7926(8) 0.56164(15) 0.7317(4) 0.0265(10) Uani 1 1 d . . . . .
C2 C 0.8987(10) 0.53474(17) 0.8220(4) 0.0308(11) Uani 1 1 d . . . . .
H2A H 0.9651 0.5526 0.8808 0.037 Uiso 1 1 calc R . . . .
H2B H 0.7890 0.5154 0.8561 0.037 Uiso 1 1 calc R . . . .
C3 C 1.0724(8) 0.51076(16) 0.7605(4) 0.0293(11) Uani 1 1 d . . . . .
H3 H 1.1865 0.4952 0.7961 0.035 Uiso 1 1 calc R . . . .
C4 C 1.0511(9) 0.51347(16) 0.6497(5) 0.0298(11) Uani 1 1 d . . . . .
C5 C 0.8474(9) 0.54001(15) 0.6205(4) 0.0262(10) Uani 1 1 d . . . . .
H5 H 0.7233 0.5202 0.6025 0.031 Uiso 1 1 calc R . . . .
C6 C 0.8685(8) 0.57128(16) 0.5251(4) 0.0255(10) Uani 1 1 d . . . . .
H6 H 0.9701 0.5946 0.5481 0.031 Uiso 1 1 calc R . . . .
C7 C 0.6523(8) 0.59034(16) 0.4810(4) 0.0265(10) Uani 1 1 d . . . . .
H7 H 0.5425 0.5670 0.4717 0.032 Uiso 1 1 calc R . . . .
C8 C 0.5498(8) 0.62366(16) 0.5563(4) 0.0271(10) Uani 1 1 d . . . . .
H8A H 0.4319 0.6386 0.5147 0.033 Uiso 1 1 calc R . . . .
H8B H 0.6649 0.6446 0.5758 0.033 Uiso 1 1 calc R . . . .
C9 C 0.4512(9) 0.60584(17) 0.6633(4) 0.0294(11) Uani 1 1 d . . . . .
H9A H 0.3570 0.5814 0.6434 0.035 Uiso 1 1 calc R . . . .
H9B H 0.3529 0.6276 0.6958 0.035 Uiso 1 1 calc R . . . .
C10 C 0.6135(9) 0.59165(16) 0.7533(4) 0.0288(11) Uani 1 1 d . . . . .
C11 C 0.7274(8) 0.60453(16) 0.3649(4) 0.0253(10) Uani 1 1 d . . . . .
H11 H 0.8147 0.6312 0.3731 0.030 Uiso 1 1 calc R . . . .
C12 C 0.8869(9) 0.56918(16) 0.3341(4) 0.0276(10) Uani 1 1 d . . . . .
C13 C 0.5576(8) 0.61097(16) 0.2723(4) 0.0273(10) Uani 1 1 d . . . . .
H13A H 0.4623 0.5856 0.2693 0.033 Uiso 1 1 calc R . . . .
H13B H 0.6388 0.6125 0.2009 0.033 Uiso 1 1 calc R . . . .
C14 C 0.5183(9) 0.59589(18) 0.8676(4) 0.0320(12) Uani 1 1 d . . . . .
H14A H 0.6207 0.5835 0.9218 0.048 Uiso 1 1 calc GR . . . .
H14B H 0.3758 0.5811 0.8711 0.048 Uiso 1 1 calc GR . . . .
H14C H 0.4962 0.6258 0.8848 0.048 Uiso 1 1 calc GR . . . .
C15 C 1.1909(9) 0.49102(17) 0.5668(5) 0.0334(12) Uani 1 1 d . . . . .
H15A H 1.0966 0.4733 0.5195 0.050 Uiso 1 1 calc GR . . . .
H15B H 1.2989 0.4732 0.6055 0.050 Uiso 1 1 calc GR . . . .
H15C H 1.2691 0.5117 0.5206 0.050 Uiso 1 1 calc GR . . . .
C16 C 0.5514(8) 0.70212(17) 0.3112(4) 0.0261(10) Uani 1 1 d . . . . .
C17 C 0.4596(10) 0.73406(18) 0.3769(4) 0.0342(12) Uani 1 1 d . . . . .
H17 H 0.3164 0.7307 0.4084 0.041 Uiso 1 1 calc R . . . .
C18 C 0.5812(12) 0.77100(19) 0.3957(5) 0.0439(15) Uani 1 1 d . . . . .
H18 H 0.5205 0.7930 0.4398 0.053 Uiso 1 1 calc R . . . .
C19 C 0.7910(11) 0.77532(19) 0.3496(5) 0.0438(15) Uani 1 1 d . . . . .
H19 H 0.8734 0.8004 0.3622 0.053 Uiso 1 1 calc R . . . .
C20 C 0.8808(10) 0.74346(18) 0.2856(5) 0.0366(12) Uani 1 1 d . . . . .
H20 H 1.0244 0.7467 0.2544 0.044 Uiso 1 1 calc R . . . .
C21 C 0.7619(8) 0.70681(16) 0.2668(4) 0.0282(10) Uani 1 1 d . . . . .
H21 H 0.8247 0.6848 0.2234 0.034 Uiso 1 1 calc R . . . .
C22 C 0.2784(8) 0.66629(16) 0.1394(4) 0.0256(10) Uani 1 1 d . . . . .
C23 C 0.1326(9) 0.63759(18) 0.0936(4) 0.0302(11) Uani 1 1 d . . . . .
H23 H 0.0949 0.6126 0.1328 0.036 Uiso 1 1 calc R . . . .
C24 C 0.0412(10) 0.6455(2) -0.0106(5) 0.0382(13) Uani 1 1 d . . . . .
H24 H -0.0607 0.6260 -0.0420 0.046 Uiso 1 1 calc R . . . .
C25 C 0.0979(10) 0.68149(19) -0.0683(5) 0.0372(13) Uani 1 1 d . . . . .
H25 H 0.0364 0.6866 -0.1397 0.045 Uiso 1 1 calc R . . . .
C26 C 0.2434(11) 0.7100(2) -0.0224(5) 0.0403(14) Uani 1 1 d . . . . .
H26 H 0.2815 0.7349 -0.0619 0.048 Uiso 1 1 calc R . . . .
C27 C 0.3343(9) 0.70226(18) 0.0813(5) 0.0345(12) Uani 1 1 d . . . . .
H27 H 0.4358 0.7219 0.1127 0.041 Uiso 1 1 calc R . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 O1 1.485(4) . ?
P1 C13 1.816(5) . ?
P1 C16 1.812(5) . ?
P1 C22 1.834(5) . ?
O2 C1 1.449(6) . ?
O2 C10 1.456(6) . ?
O3 C6 1.464(6) . ?
O3 C12 1.355(6) . ?
O4 C12 1.197(6) . ?
C1 C2 1.522(7) . ?
C1 C5 1.539(7) . ?
C1 C10 1.463(7) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C2 C3 1.491(8) . ?
C3 H3 0.9500 . ?
C3 C4 1.342(7) . ?
C4 C5 1.530(7) . ?
C4 C15 1.488(8) . ?
C5 H5 1.0000 . ?
C5 C6 1.522(7) . ?
C6 H6 1.0000 . ?
C6 C7 1.533(7) . ?
C7 H7 1.0000 . ?
C7 C8 1.523(7) . ?
C7 C11 1.535(7) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.527(7) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.527(7) . ?
C10 C14 1.496(7) . ?
C11 H11 1.0000 . ?
C11 C12 1.523(7) . ?
C11 C13 1.528(7) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?
C16 C17 1.399(7) . ?
C16 C21 1.386(7) . ?
C17 H17 0.9500 . ?
C17 C18 1.400(9) . ?
C18 H18 0.9500 . ?
C18 C19 1.389(10) . ?
C19 H19 0.9500 . ?
C19 C20 1.381(9) . ?
C20 H20 0.9500 . ?
C20 C21 1.384(8) . ?
C21 H21 0.9500 . ?
C22 C23 1.381(7) . ?
C22 C27 1.379(7) . ?
C23 H23 0.9500 . ?
C23 C24 1.391(8) . ?
C24 H24 0.9500 . ?
C24 C25 1.379(9) . ?
C25 H25 0.9500 . ?
C25 C26 1.375(9) . ?
C26 H26 0.9500 . ?
C26 C27 1.385(8) . ?
C27 H27 0.9500 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 P1 C13 113.4(2) . . ?
O1 P1 C16 112.9(2) . . ?
O1 P1 C22 112.4(2) . . ?
C13 P1 C22 105.7(2) . . ?
C16 P1 C13 107.6(2) . . ?
C16 P1 C22 104.2(2) . . ?
C1 O2 C10 60.5(3) . . ?
C12 O3 C6 109.4(4) . . ?
O2 C1 C2 114.6(4) . . ?
O2 C1 C5 116.8(4) . . ?
O2 C1 C10 60.0(3) . . ?
C2 C1 C5 106.2(4) . . ?
C10 C1 C2 123.3(4) . . ?
C10 C1 C5 127.0(4) . . ?
C1 C2 H2A 111.1 . . ?
C1 C2 H2B 111.1 . . ?
H2A C2 H2B 109.1 . . ?
C3 C2 C1 103.2(4) . . ?
C3 C2 H2A 111.1 . . ?
C3 C2 H2B 111.1 . . ?
C2 C3 H3 123.4 . . ?
C4 C3 C2 113.1(5) . . ?
C4 C3 H3 123.4 . . ?
C3 C4 C5 109.9(5) . . ?
C3 C4 C15 125.5(5) . . ?
C15 C4 C5 124.4(5) . . ?
C1 C5 H5 107.9 . . ?
C4 C5 C1 102.6(4) . . ?
C4 C5 H5 107.9 . . ?
C6 C5 C1 112.5(4) . . ?
C6 C5 C4 117.6(4) . . ?
C6 C5 H5 107.9 . . ?
O3 C6 C5 109.7(4) . . ?
O3 C6 H6 109.0 . . ?
O3 C6 C7 103.3(4) . . ?
C5 C6 H6 109.0 . . ?
C5 C6 C7 116.5(4) . . ?
C7 C6 H6 109.0 . . ?
C6 C7 H7 108.1 . . ?
C6 C7 C11 100.3(4) . . ?
C8 C7 C6 114.4(4) . . ?
C8 C7 H7 108.1 . . ?
C8 C7 C11 117.2(4) . . ?
C11 C7 H7 108.1 . . ?
C7 C8 H8A 108.8 . . ?
C7 C8 H8B 108.8 . . ?
C7 C8 C9 113.8(4) . . ?
H8A C8 H8B 107.7 . . ?
C9 C8 H8A 108.8 . . ?
C9 C8 H8B 108.8 . . ?
C8 C9 H9A 108.0 . . ?
C8 C9 H9B 108.0 . . ?
C8 C9 C10 117.2(4) . . ?
H9A C9 H9B 107.3 . . ?
C10 C9 H9A 108.0 . . ?
C10 C9 H9B 108.0 . . ?
O2 C10 C1 59.5(3) . . ?
O2 C10 C9 115.5(4) . . ?
O2 C10 C14 115.8(4) . . ?
C1 C10 C9 122.7(4) . . ?
C1 C10 C14 120.3(5) . . ?
C14 C10 C9 112.3(4) . . ?
C7 C11 H11 108.2 . . ?
C12 C11 C7 101.1(4) . . ?
C12 C11 H11 108.2 . . ?
C12 C11 C13 110.2(4) . . ?
C13 C11 C7 120.3(4) . . ?
C13 C11 H11 108.2 . . ?
O3 C12 C11 109.7(4) . . ?
O4 C12 O3 121.7(5) . . ?
O4 C12 C11 128.5(5) . . ?
P1 C13 H13A 107.9 . . ?
P1 C13 H13B 107.9 . . ?
C11 C13 P1 117.6(4) . . ?
C11 C13 H13A 107.9 . . ?
C11 C13 H13B 107.9 . . ?
H13A C13 H13B 107.2 . . ?
C10 C14 H14A 109.5 . . ?
C10 C14 H14B 109.5 . . ?
C10 C14 H14C 109.5 . . ?
H14A C14 H14B 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C4 C15 H15A 109.5 . . ?
C4 C15 H15B 109.5 . . ?
C4 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
C17 C16 P1 117.2(4) . . ?
C21 C16 P1 122.5(4) . . ?
C21 C16 C17 120.2(5) . . ?
C16 C17 H17 120.4 . . ?
C16 C17 C18 119.3(6) . . ?
C18 C17 H17 120.4 . . ?
C17 C18 H18 120.1 . . ?
C19 C18 C17 119.7(6) . . ?
C19 C18 H18 120.1 . . ?
C18 C19 H19 119.7 . . ?
C20 C19 C18 120.6(6) . . ?
C20 C19 H19 119.7 . . ?
C19 C20 H20 120.0 . . ?
C19 C20 C21 120.1(6) . . ?
C21 C20 H20 120.0 . . ?
C16 C21 H21 119.9 . . ?
C20 C21 C16 120.2(5) . . ?
C20 C21 H21 119.9 . . ?
C23 C22 P1 118.3(4) . . ?
C27 C22 P1 121.7(4) . . ?
C27 C22 C23 119.9(5) . . ?
C22 C23 H23 120.2 . . ?
C22 C23 C24 119.6(5) . . ?
C24 C23 H23 120.2 . . ?
C23 C24 H24 119.9 . . ?
C25 C24 C23 120.3(6) . . ?
C25 C24 H24 119.9 . . ?
C24 C25 H25 120.0 . . ?
C26 C25 C24 120.0(5) . . ?
C26 C25 H25 120.0 . . ?
C25 C26 H26 120.1 . . ?
C25 C26 C27 119.9(6) . . ?
C27 C26 H26 120.1 . . ?
C22 C27 C26 120.4(6) . . ?
C22 C27 H27 119.8 . . ?
C26 C27 H27 119.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
P1 C16 C17 C18 -175.5(4) . . . . ?
P1 C16 C21 C20 175.1(4) . . . . ?
P1 C22 C23 C24 175.3(4) . . . . ?
P1 C22 C27 C26 -175.3(5) . . . . ?
O1 P1 C13 C11 -77.7(4) . . . . ?
O1 P1 C16 C17 -21.2(5) . . . . ?
O1 P1 C16 C21 162.4(4) . . . . ?
O1 P1 C22 C23 -54.9(5) . . . . ?
O1 P1 C22 C27 121.0(5) . . . . ?
O2 C1 C2 C3 -109.6(5) . . . . ?
O2 C1 C5 C4 107.6(4) . . . . ?
O2 C1 C5 C6 -19.8(6) . . . . ?
O2 C1 C10 C9 102.5(5) . . . . ?
O2 C1 C10 C14 -103.9(5) . . . . ?
O3 C6 C7 C8 -164.9(4) . . . . ?
O3 C6 C7 C11 -38.5(4) . . . . ?
C1 O2 C10 C9 -114.4(5) . . . . ?
C1 O2 C10 C14 111.5(5) . . . . ?
C1 C2 C3 C4 -12.5(6) . . . . ?
C1 C5 C6 O3 169.1(4) . . . . ?
C1 C5 C6 C7 -73.9(5) . . . . ?
C2 C1 C5 C4 -21.7(5) . . . . ?
C2 C1 C5 C6 -149.0(4) . . . . ?
C2 C1 C10 O2 101.3(5) . . . . ?
C2 C1 C10 C9 -156.2(5) . . . . ?
C2 C1 C10 C14 -2.6(7) . . . . ?
C2 C3 C4 C5 -1.4(7) . . . . ?
C2 C3 C4 C15 -176.2(5) . . . . ?
C3 C4 C5 C1 14.6(6) . . . . ?
C3 C4 C5 C6 138.6(5) . . . . ?
C4 C5 C6 O3 50.2(6) . . . . ?
C4 C5 C6 C7 167.1(4) . . . . ?
C5 C1 C2 C3 21.0(5) . . . . ?
C5 C1 C10 O2 -102.5(5) . . . . ?
C5 C1 C10 C9 0.0(8) . . . . ?
C5 C1 C10 C14 153.6(5) . . . . ?
C5 C6 C7 C8 74.7(6) . . . . ?
C5 C6 C7 C11 -158.9(4) . . . . ?
C6 O3 C12 O4 179.4(5) . . . . ?
C6 O3 C12 C11 -2.0(5) . . . . ?
C6 C7 C8 C9 -70.9(6) . . . . ?
C6 C7 C11 C12 36.3(5) . . . . ?
C6 C7 C11 C13 157.7(4) . . . . ?
C7 C8 C9 C10 73.8(6) . . . . ?
C7 C11 C12 O3 -22.7(5) . . . . ?
C7 C11 C12 O4 155.8(5) . . . . ?
C7 C11 C13 P1 72.6(5) . . . . ?
C8 C7 C11 C12 160.8(4) . . . . ?
C8 C7 C11 C13 -77.8(6) . . . . ?
C8 C9 C10 O2 15.1(7) . . . . ?
C8 C9 C10 C1 -53.7(7) . . . . ?
C8 C9 C10 C14 150.8(5) . . . . ?
C10 O2 C1 C2 -115.6(5) . . . . ?
C10 O2 C1 C5 119.2(5) . . . . ?
C10 C1 C2 C3 -178.6(5) . . . . ?
C10 C1 C5 C4 178.9(5) . . . . ?
C10 C1 C5 C6 51.5(7) . . . . ?
C11 C7 C8 C9 172.0(4) . . . . ?
C12 O3 C6 C5 151.0(4) . . . . ?
C12 O3 C6 C7 26.1(5) . . . . ?
C12 C11 C13 P1 -170.6(3) . . . . ?
C13 P1 C16 C17 -147.0(4) . . . . ?
C13 P1 C16 C21 36.6(5) . . . . ?
C13 P1 C22 C23 69.3(4) . . . . ?
C13 P1 C22 C27 -114.8(5) . . . . ?
C13 C11 C12 O3 -151.0(4) . . . . ?
C13 C11 C12 O4 27.5(8) . . . . ?
C15 C4 C5 C1 -170.6(5) . . . . ?
C15 C4 C5 C6 -46.5(7) . . . . ?
C16 P1 C13 C11 47.9(4) . . . . ?
C16 P1 C22 C23 -177.4(4) . . . . ?
C16 P1 C22 C27 -1.5(5) . . . . ?
C16 C17 C18 C19 -0.4(8) . . . . ?
C17 C16 C21 C20 -1.2(7) . . . . ?
C17 C18 C19 C20 -0.1(9) . . . . ?
C18 C19 C20 C21 0.0(9) . . . . ?
C19 C20 C21 C16 0.7(8) . . . . ?
C21 C16 C17 C18 1.0(7) . . . . ?
C22 P1 C13 C11 158.8(4) . . . . ?
C22 P1 C16 C17 101.0(4) . . . . ?
C22 P1 C16 C21 -75.4(4) . . . . ?
C22 C23 C24 C25 0.8(8) . . . . ?
C23 C22 C27 C26 0.6(8) . . . . ?
C23 C24 C25 C26 -0.7(9) . . . . ?
C24 C25 C26 C27 0.6(9) . . . . ?
C25 C26 C27 C22 -0.5(9) . . . . ?
C27 C22 C23 C24 -0.8(8) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.751
_oxdiff_exptl_absorpt_empirical_full_min 0.648

