# Electronic Supplementary Material (ESI) for Green 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_P21N
_database_code_depnum_ccdc_archive 'CCDC 1903624'
loop_
_audit_author_name
_audit_author_address
'Jian-Jun Liu'
;Qujing Normal University
China
;
_audit_update_record             
;
2019-03-16 deposited with the CCDC.	2019-05-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C26 H24 N O4 P S'
_chemical_formula_sum            'C26 H24 N O4 P S'
_chemical_formula_weight         477.49

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'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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

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

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

_cell_length_a                   10.393(5)
_cell_length_b                   18.063(9)
_cell_length_c                   12.568(6)
_cell_angle_alpha                90
_cell_angle_beta                 99.096(10)
_cell_angle_gamma                90
_cell_volume                     2330(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    14810
_cell_measurement_theta_min      2.63
_cell_measurement_theta_max      28.35

_exptl_crystal_description       needlelike
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.361
_exptl_crystal_F_000             1000
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.17
_exptl_absorpt_coefficient_mu    0.241
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9124
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   '(SADABS; Bruker, 2004)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14541
_diffrn_reflns_av_unetI/netI     0.1802
_diffrn_reflns_av_R_equivalents  0.1146
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         2.255
_diffrn_reflns_theta_max         28.577
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.966
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.966
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.966
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             5739
_reflns_number_gt                2389
_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       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SMART'
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.1679P)²+0.5324P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5739
_refine_ls_number_parameters     300
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.2220
_refine_ls_R_factor_gt           0.1215
_refine_ls_wR_factor_ref         0.3678
_refine_ls_wR_factor_gt          0.3121
_refine_ls_goodness_of_fit_ref   1.038
_refine_ls_restrained_S_all      1.038
_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
P2 P 0.34735(17) 0.81165(8) 0.61290(12) 0.0432(5) Uani 1 1 d . . . . .
S1 S 0.3307(2) 0.86105(9) 0.94349(13) 0.0552(5) Uani 1 1 d . . . . .
O3 O 0.2252(4) 0.8376(2) 0.6445(3) 0.0531(12) Uani 1 1 d . . . . .
O4 O 0.8321(5) 0.8593(3) 0.6877(4) 0.0630(13) Uani 1 1 d . . . . .
O2 O 0.4342(5) 0.8832(3) 1.0251(3) 0.0665(14) Uani 1 1 d . . . . .
O1 O 0.2011(6) 0.8813(3) 0.9517(4) 0.0752(16) Uani 1 1 d . . . . .
N1 N 0.3566(5) 0.8953(3) 0.8293(4) 0.0478(13) Uani 1 1 d . . . . .
H1 H 0.2956 0.9193 0.7895 0.057 Uiso 1 1 calc R U . . .
C8 C 0.4798(7) 0.8859(3) 0.7946(5) 0.0432(15) Uani 1 1 d . . . . .
C13 C 0.4869(6) 0.8496(3) 0.6978(4) 0.0385(14) Uani 1 1 d . . . . .
C12 C 0.6096(6) 0.8444(3) 0.6653(4) 0.0401(14) Uani 1 1 d . . . . .
H12 H 0.6164 0.8221 0.5998 0.048 Uiso 1 1 calc R U . . .
C11 C 0.7183(6) 0.8710(3) 0.7268(5) 0.0431(14) Uani 1 1 d . . . . .
C10 C 0.7110(7) 0.9063(3) 0.8231(5) 0.0480(16) Uani 1 1 d . . . . .
H10 H 0.7856 0.9237 0.8666 0.058 Uiso 1 1 calc R U . . .
C9 C 0.5905(7) 0.9148(3) 0.8526(5) 0.0504(16) Uani 1 1 d . . . . .
H9 H 0.5839 0.9415 0.9148 0.060 Uiso 1 1 calc R U . . .
C21 C 0.3609(7) 0.7128(3) 0.6136(5) 0.0460(15) Uani 1 1 d . . . . .
C15 C 0.3618(6) 0.8408(3) 0.4794(4) 0.0437(15) Uani 1 1 d . . . . .
C6 C 0.2239(7) 0.7261(4) 0.9035(5) 0.0582(18) Uani 1 1 d . . . . .
H6 H 0.1444 0.7508 0.8925 0.070 Uiso 1 1 calc R U . . .
C26 C 0.2503(7) 0.6742(3) 0.6279(5) 0.0550(17) Uani 1 1 d . . . . .
H26 H 0.1755 0.6994 0.6389 0.066 Uiso 1 1 calc R U . . .
C25 C 0.2517(8) 0.5970(4) 0.6258(5) 0.0581(19) Uani 1 1 d . . . . .
H25 H 0.1775 0.5706 0.6349 0.070 Uiso 1 1 calc R U . . .
C1 C 0.3368(7) 0.7654(3) 0.9313(5) 0.0497(16) Uani 1 1 d . . . . .
C16 C 0.3846(8) 0.9133(3) 0.4599(5) 0.058(2) Uani 1 1 d . . . . .
H16 H 0.4006 0.9459 0.5178 0.070 Uiso 1 1 calc R U . . .
C22 C 0.4687(8) 0.6746(4) 0.6001(6) 0.067(2) Uani 1 1 d . . . . .
H22 H 0.5438 0.7004 0.5915 0.080 Uiso 1 1 calc R U . . .
C24 C 0.3620(9) 0.5603(4) 0.6105(6) 0.068(2) Uani 1 1 d . . . . .
H24 H 0.3627 0.5088 0.6083 0.081 Uiso 1 1 calc R U . . .
C20 C 0.3409(8) 0.7937(4) 0.3915(5) 0.065(2) Uani 1 1 d . . . . .
H20 H 0.3268 0.7436 0.4015 0.078 Uiso 1 1 calc R U . . .
C14 C 0.9470(8) 0.8882(5) 0.7446(7) 0.084(3) Uani 1 1 d . . . . .
H14A H 0.9416 0.9412 0.7458 0.126 Uiso 1 1 calc R U . . .
H14B H 1.0192 0.8736 0.7102 0.126 Uiso 1 1 calc R U . . .
H14C H 0.9595 0.8696 0.8171 0.126 Uiso 1 1 calc R U . . .
C23 C 0.4701(9) 0.5988(4) 0.5986(7) 0.073(2) Uani 1 1 d . . . . .
H23 H 0.5458 0.5737 0.5894 0.087 Uiso 1 1 calc R U . . .
C4 C 0.3437(9) 0.6142(4) 0.9106(6) 0.067(2) Uani 1 1 d . . . . .
C5 C 0.2264(9) 0.6513(4) 0.8918(6) 0.071(2) Uani 1 1 d . . . . .
H5 H 0.1493 0.6253 0.8712 0.085 Uiso 1 1 calc R U . . .
C2 C 0.4532(8) 0.7283(4) 0.9497(6) 0.070(2) Uani 1 1 d . . . . .
H2 H 0.5305 0.7544 0.9693 0.084 Uiso 1 1 calc R U . . .
C17 C 0.3849(8) 0.9400(4) 0.3580(5) 0.068(2) Uani 1 1 d . . . . .
H17 H 0.4013 0.9898 0.3472 0.082 Uiso 1 1 calc R U . . .
C3 C 0.4558(9) 0.6530(4) 0.9390(7) 0.081(3) Uani 1 1 d . . . . .
H3 H 0.5351 0.6281 0.9514 0.097 Uiso 1 1 calc R U . . .
C18 C 0.3608(9) 0.8927(4) 0.2725(6) 0.074(2) Uani 1 1 d . . . . .
H18 H 0.3583 0.9102 0.2027 0.089 Uiso 1 1 calc R U . . .
C19 C 0.3409(10) 0.8209(4) 0.2900(6) 0.082(3) Uani 1 1 d . . . . .
H19 H 0.3267 0.7887 0.2317 0.098 Uiso 1 1 calc R U . . .
C7 C 0.3477(11) 0.5305(4) 0.9013(8) 0.106(3) Uani 1 1 d . . . . .
H7A H 0.3520 0.5088 0.9715 0.159 Uiso 1 1 calc R U . . .
H7B H 0.4232 0.5162 0.8710 0.159 Uiso 1 1 calc R U . . .
H7C H 0.2706 0.5135 0.8555 0.159 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
P2 O3 1.466(5) . ?
P2 C15 1.787(6) . ?
P2 C21 1.791(6) . ?
P2 C13 1.795(6) . ?
S1 O1 1.416(6) . ?
S1 O2 1.421(5) . ?
S1 N1 1.624(5) . ?
S1 C1 1.736(7) . ?
O4 C11 1.367(8) . ?
O4 C14 1.393(9) . ?
N1 C8 1.426(8) . ?
N1 H1 0.8600 . ?
C8 C9 1.365(9) . ?
C8 C13 1.395(8) . ?
C13 C12 1.402(8) . ?
C12 C11 1.352(9) . ?
C12 H12 0.9300 . ?
C11 C10 1.381(8) . ?
C10 C9 1.370(9) . ?
C10 H10 0.9300 . ?
C9 H9 0.9300 . ?
C21 C22 1.349(9) . ?
C21 C26 1.381(9) . ?
C15 C16 1.361(8) . ?
C15 C20 1.384(8) . ?
C6 C5 1.359(10) . ?
C6 C1 1.369(9) . ?
C6 H6 0.9300 . ?
C26 C25 1.394(9) . ?
C26 H26 0.9300 . ?
C25 C24 1.364(11) . ?
C25 H25 0.9300 . ?
C1 C2 1.371(9) . ?
C16 C17 1.368(9) . ?
C16 H16 0.9300 . ?
C22 C23 1.371(9) . ?
C22 H22 0.9300 . ?
C24 C23 1.349(11) . ?
C24 H24 0.9300 . ?
C20 C19 1.367(10) . ?
C20 H20 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C23 H23 0.9300 . ?
C4 C3 1.358(11) . ?
C4 C5 1.378(11) . ?
C4 C7 1.518(10) . ?
C5 H5 0.9300 . ?
C2 C3 1.369(10) . ?
C2 H2 0.9300 . ?
C17 C18 1.365(9) . ?
C17 H17 0.9300 . ?
C3 H3 0.9300 . ?
C18 C19 1.336(9) . ?
C18 H18 0.9300 . ?
C19 H19 0.9300 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 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
O3 P2 C15 111.4(3) . . ?
O3 P2 C21 112.9(3) . . ?
C15 P2 C21 106.3(3) . . ?
O3 P2 C13 111.7(3) . . ?
C15 P2 C13 105.4(3) . . ?
C21 P2 C13 108.8(3) . . ?
O1 S1 O2 119.6(3) . . ?
O1 S1 N1 105.0(3) . . ?
O2 S1 N1 108.6(3) . . ?
O1 S1 C1 108.2(3) . . ?
O2 S1 C1 108.1(3) . . ?
N1 S1 C1 106.7(3) . . ?
C11 O4 C14 118.6(6) . . ?
C8 N1 S1 120.5(4) . . ?
C8 N1 H1 119.8 . . ?
S1 N1 H1 119.8 . . ?
C9 C8 C13 119.3(6) . . ?
C9 C8 N1 120.9(6) . . ?
C13 C8 N1 119.8(6) . . ?
C8 C13 C12 117.5(6) . . ?
C8 C13 P2 123.3(5) . . ?
C12 C13 P2 119.2(4) . . ?
C11 C12 C13 121.8(5) . . ?
C11 C12 H12 119.1 . . ?
C13 C12 H12 119.1 . . ?
C12 C11 O4 115.6(5) . . ?
C12 C11 C10 120.5(6) . . ?
O4 C11 C10 123.8(6) . . ?
C9 C10 C11 117.9(6) . . ?
C9 C10 H10 121.0 . . ?
C11 C10 H10 121.0 . . ?
C8 C9 C10 122.8(6) . . ?
C8 C9 H9 118.6 . . ?
C10 C9 H9 118.6 . . ?
C22 C21 C26 118.9(6) . . ?
C22 C21 P2 125.1(5) . . ?
C26 C21 P2 116.0(5) . . ?
C16 C15 C20 117.2(6) . . ?
C16 C15 P2 119.7(4) . . ?
C20 C15 P2 122.9(5) . . ?
C5 C6 C1 120.9(7) . . ?
C5 C6 H6 119.6 . . ?
C1 C6 H6 119.6 . . ?
C21 C26 C25 119.4(7) . . ?
C21 C26 H26 120.3 . . ?
C25 C26 H26 120.3 . . ?
C24 C25 C26 120.1(7) . . ?
C24 C25 H25 120.0 . . ?
C26 C25 H25 120.0 . . ?
C2 C1 C6 119.2(6) . . ?
C2 C1 S1 121.0(6) . . ?
C6 C1 S1 119.8(6) . . ?
C15 C16 C17 122.2(6) . . ?
C15 C16 H16 118.9 . . ?
C17 C16 H16 118.9 . . ?
C21 C22 C23 121.6(7) . . ?
C21 C22 H22 119.2 . . ?
C23 C22 H22 119.2 . . ?
C23 C24 C25 119.9(6) . . ?
C23 C24 H24 120.1 . . ?
C25 C24 H24 120.1 . . ?
C19 C20 C15 120.1(6) . . ?
C19 C20 H20 119.9 . . ?
C15 C20 H20 119.9 . . ?
O4 C14 H14A 109.5 . . ?
O4 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O4 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C24 C23 C22 120.2(8) . . ?
C24 C23 H23 119.9 . . ?
C22 C23 H23 119.9 . . ?
C3 C4 C5 119.6(7) . . ?
C3 C4 C7 120.0(8) . . ?
C5 C4 C7 120.4(8) . . ?
C6 C5 C4 119.8(8) . . ?
C6 C5 H5 120.1 . . ?
C4 C5 H5 120.1 . . ?
C1 C2 C3 120.0(7) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?
C18 C17 C16 119.3(6) . . ?
C18 C17 H17 120.3 . . ?
C16 C17 H17 120.3 . . ?
C4 C3 C2 120.6(8) . . ?
C4 C3 H3 119.7 . . ?
C2 C3 H3 119.7 . . ?
C19 C18 C17 119.5(6) . . ?
C19 C18 H18 120.3 . . ?
C17 C18 H18 120.3 . . ?
C18 C19 C20 121.6(6) . . ?
C18 C19 H19 119.2 . . ?
C20 C19 H19 119.2 . . ?
C4 C7 H7A 109.5 . . ?
C4 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C4 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?

_refine_diff_density_max         0.936
_refine_diff_density_min         -0.431
_refine_diff_density_rms         0.116

####################################################################### 
# 
# 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_3ap
_database_code_depnum_ccdc_archive 'CCDC 1903625'
loop_
_audit_author_name
_audit_author_address
'Jian-Jun Liu'
;Qujing Normal University
China
;
_audit_update_record             
;
2019-03-16 deposited with the CCDC.	2019-05-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C27 H26 N O5 P S'
_chemical_formula_sum            'C27 H26 N O5 P S'
_chemical_formula_weight         507.52

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

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

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

_cell_length_a                   10.8200(9)
_cell_length_b                   17.6091(15)
_cell_length_c                   14.0022(13)
_cell_angle_alpha                90
_cell_angle_beta                 105.494(2)
_cell_angle_gamma                90
_cell_volume                     2570.9(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    15394
_cell_measurement_theta_min      2.762
_cell_measurement_theta_max      27.553

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.311
_exptl_crystal_F_000             1064
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.226
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8564
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   '(SADABS; Bruker, 2004)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15394
_diffrn_reflns_av_unetI/netI     0.0590
_diffrn_reflns_av_R_equivalents  0.0428
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.762
_diffrn_reflns_theta_max         27.553
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5828
_reflns_number_gt                3662
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.0769P)²+0.2620P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5828
_refine_ls_number_parameters     319
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0982
_refine_ls_R_factor_gt           0.0557
_refine_ls_wR_factor_ref         0.1547
_refine_ls_wR_factor_gt          0.1316
_refine_ls_goodness_of_fit_ref   1.016
_refine_ls_restrained_S_all      1.016
_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
S1 S 0.56405(6) 0.10993(4) 0.67453(5) 0.04157(19) Uani 1 1 d . . . . .
P1 P 0.27349(6) 0.08383(4) 0.82797(5) 0.03821(19) Uani 1 1 d . . . . .
O1 O 0.40054(17) 0.11799(11) 0.87808(13) 0.0503(5) Uani 1 1 d . . . . .
O2 O 0.67132(16) 0.14838(11) 0.73760(16) 0.0594(6) Uani 1 1 d . . . . .
O3 O 0.54609(17) 0.11059(11) 0.56954(14) 0.0530(5) Uani 1 1 d . . . . .
O4 O 0.08824(18) 0.13992(14) 0.39514(14) 0.0687(6) Uani 1 1 d . . . . .
O5 O -0.07312(17) 0.10305(13) 0.49102(14) 0.0644(6) Uani 1 1 d . . . . .
N1 N 0.43771(18) 0.14867(11) 0.69770(16) 0.0405(5) Uani 1 1 d . . . . .
H1 H 0.4495 0.1825 0.7436 0.049 Uiso 1 1 d R U . . .
C1 C 0.2225(2) 0.10773(13) 0.69849(17) 0.0347(5) Uani 1 1 d . . . . .
C2 C 0.3089(2) 0.12977(13) 0.64588(17) 0.0339(5) Uani 1 1 d . . . . .
C3 C 0.2655(2) 0.14129(14) 0.54334(19) 0.0412(6) Uani 1 1 d . . . . .
H3 H 0.3233 0.1564 0.5084 0.049 Uiso 1 1 calc R U . . .
C4 C 0.1392(2) 0.13067(16) 0.49389(18) 0.0442(6) Uani 1 1 d . . . . .
C5 C 0.0505(2) 0.11043(15) 0.54670(18) 0.0430(6) Uani 1 1 d . . . . .
C6 C 0.0924(2) 0.09966(14) 0.64698(18) 0.0396(6) Uani 1 1 d . . . . .
H6 H 0.0335 0.0867 0.6819 0.048 Uiso 1 1 calc R U . . .
C7 C -0.1665(3) 0.0834(2) 0.5400(2) 0.0720(10) Uani 1 1 d . . . . .
H7A H -0.1469 0.0345 0.5704 0.108 Uiso 1 1 calc R U . . .
H7B H -0.2493 0.0819 0.4930 0.108 Uiso 1 1 calc R U . . .
H7C H -0.1671 0.1206 0.5900 0.108 Uiso 1 1 calc R U . . .
C8 C 0.1691(3) 0.1652(3) 0.3374(3) 0.1092(17) Uani 1 1 d . . . . .
H8A H 0.2048 0.2137 0.3614 0.164 Uiso 1 1 calc R U . . .
H8B H 0.1204 0.1699 0.2695 0.164 Uiso 1 1 calc R U . . .
H8C H 0.2372 0.1293 0.3422 0.164 Uiso 1 1 calc R U . . .
C9 C 0.2728(2) -0.01796(14) 0.83487(17) 0.0366(5) Uani 1 1 d . . . . .
C10 C 0.3410(3) -0.05143(16) 0.9227(2) 0.0524(7) Uani 1 1 d . . . . .
H10 H 0.3855 -0.0210 0.9749 0.063 Uiso 1 1 calc R U . . .
C11 C 0.3438(3) -0.12909(18) 0.9338(2) 0.0677(9) Uani 1 1 d . . . . .
H11 H 0.3904 -0.1509 0.9929 0.081 Uiso 1 1 calc R U . . .
C12 C 0.2781(3) -0.17383(18) 0.8578(3) 0.0657(9) Uani 1 1 d . . . . .
H12 H 0.2800 -0.2263 0.8655 0.079 Uiso 1 1 calc R U . . .
C13 C 0.2092(3) -0.14254(17) 0.7701(2) 0.0609(8) Uani 1 1 d . . . . .
H13 H 0.1640 -0.1736 0.7189 0.073 Uiso 1 1 calc R U . . .
C14 C 0.2072(3) -0.06492(16) 0.7584(2) 0.0508(7) Uani 1 1 d . . . . .
H14 H 0.1615 -0.0437 0.6986 0.061 Uiso 1 1 calc R U . . .
C15 C 0.1526(3) 0.11626(16) 0.88586(19) 0.0471(7) Uani 1 1 d . . . . .
C16 C 0.1726(3) 0.18658(18) 0.9324(2) 0.0633(8) Uani 1 1 d . . . . .
H16 H 0.2422 0.2161 0.9281 0.076 Uiso 1 1 calc R U . . .
C17 C 0.0907(5) 0.2129(2) 0.9848(3) 0.0913(13) Uani 1 1 d . . . . .
H17 H 0.1053 0.2600 1.0160 0.110 Uiso 1 1 calc R U . . .
C18 C -0.0108(5) 0.1706(3) 0.9911(3) 0.1004(15) Uani 1 1 d . . . . .
H18 H -0.0658 0.1887 1.0268 0.121 Uiso 1 1 calc R U . . .
C19 C -0.0337(4) 0.1011(3) 0.9454(3) 0.1013(14) Uani 1 1 d . . . . .
H19 H -0.1048 0.0727 0.9490 0.122 Uiso 1 1 calc R U . . .
C20 C 0.0503(3) 0.0731(2) 0.8933(3) 0.0743(10) Uani 1 1 d . . . . .
H20 H 0.0368 0.0254 0.8639 0.089 Uiso 1 1 calc R U . . .
C21 C 0.5678(2) 0.01478(14) 0.71312(18) 0.0385(6) Uani 1 1 d . . . . .
C22 C 0.6317(3) -0.00478(18) 0.8083(2) 0.0673(9) Uani 1 1 d . . . . .
H22 H 0.6741 0.0321 0.8526 0.081 Uiso 1 1 calc R U . . .
C23 C 0.6329(4) -0.07951(19) 0.8380(2) 0.0773(11) Uani 1 1 d . . . . .
H23 H 0.6755 -0.0924 0.9028 0.093 Uiso 1 1 calc R U . . .
C24 C 0.5727(3) -0.13526(16) 0.7741(2) 0.0530(7) Uani 1 1 d . . . . .
C25 C 0.5085(3) -0.11406(16) 0.6802(2) 0.0603(8) Uani 1 1 d . . . . .
H25 H 0.4655 -0.1510 0.6362 0.072 Uiso 1 1 calc R U . . .
C26 C 0.5052(3) -0.03996(16) 0.6484(2) 0.0509(7) Uani 1 1 d . . . . .
H26 H 0.4611 -0.0272 0.5839 0.061 Uiso 1 1 calc R U . . .
C27 C 0.5782(4) -0.21745(18) 0.8064(3) 0.0813(11) Uani 1 1 d . . . . .
H27A H 0.5042 -0.2438 0.7675 0.122 Uiso 1 1 calc R U . . .
H27B H 0.5796 -0.2200 0.8752 0.122 Uiso 1 1 calc R U . . .
H27C H 0.6544 -0.2407 0.7970 0.122 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
S1 O2 1.4275(18) . ?
S1 O3 1.4305(19) . ?
S1 N1 1.636(2) . ?
S1 C21 1.758(3) . ?
P1 O1 1.4928(18) . ?
P1 C9 1.795(3) . ?
P1 C1 1.798(2) . ?
P1 C15 1.805(3) . ?
O4 C4 1.355(3) . ?
O4 C8 1.413(4) . ?
O5 C5 1.363(3) . ?
O5 C7 1.407(3) . ?
N1 C2 1.428(3) . ?
N1 H1 0.8599 . ?
C1 C2 1.390(3) . ?
C1 C6 1.407(3) . ?
C2 C3 1.401(3) . ?
C3 C4 1.369(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.405(4) . ?
C5 C6 1.369(3) . ?
C6 H6 0.9300 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 C10 1.386(3) . ?
C9 C14 1.389(3) . ?
C10 C11 1.376(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.362(4) . ?
C11 H11 0.9300 . ?
C12 C13 1.370(4) . ?
C12 H12 0.9300 . ?
C13 C14 1.376(4) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 C20 1.370(4) . ?
C15 C16 1.389(4) . ?
C16 C17 1.373(5) . ?
C16 H16 0.9300 . ?
C17 C18 1.349(6) . ?
C17 H17 0.9300 . ?
C18 C19 1.373(6) . ?
C18 H18 0.9300 . ?
C19 C20 1.398(5) . ?
C19 H19 0.9300 . ?
C20 H20 0.9300 . ?
C21 C26 1.371(4) . ?
C21 C22 1.372(4) . ?
C22 C23 1.379(4) . ?
C22 H22 0.9300 . ?
C23 C24 1.369(4) . ?
C23 H23 0.9300 . ?
C24 C25 1.365(4) . ?
C24 C27 1.513(4) . ?
C25 C26 1.376(4) . ?
C25 H25 0.9300 . ?
C26 H26 0.9300 . ?
C27 H27A 0.9600 . ?
C27 H27B 0.9600 . ?
C27 H27C 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
O2 S1 O3 119.78(12) . . ?
O2 S1 N1 105.31(11) . . ?
O3 S1 N1 108.01(11) . . ?
O2 S1 C21 108.29(12) . . ?
O3 S1 C21 108.02(12) . . ?
N1 S1 C21 106.76(11) . . ?
O1 P1 C9 113.17(11) . . ?
O1 P1 C1 112.05(11) . . ?
C9 P1 C1 106.46(11) . . ?
O1 P1 C15 110.37(12) . . ?
C9 P1 C15 106.13(12) . . ?
C1 P1 C15 108.35(11) . . ?
C4 O4 C8 118.4(2) . . ?
C5 O5 C7 117.9(2) . . ?
C2 N1 S1 123.78(16) . . ?
C2 N1 H1 118.1 . . ?
S1 N1 H1 118.1 . . ?
C2 C1 C6 118.6(2) . . ?
C2 C1 P1 122.08(17) . . ?
C6 C1 P1 119.24(18) . . ?
C1 C2 C3 119.7(2) . . ?
C1 C2 N1 119.9(2) . . ?
C3 C2 N1 120.1(2) . . ?
C4 C3 C2 121.0(2) . . ?
C4 C3 H3 119.5 . . ?
C2 C3 H3 119.5 . . ?
O4 C4 C3 125.4(2) . . ?
O4 C4 C5 114.7(2) . . ?
C3 C4 C5 119.9(2) . . ?
O5 C5 C6 125.4(2) . . ?
O5 C5 C4 115.3(2) . . ?
C6 C5 C4 119.3(2) . . ?
C5 C6 C1 121.6(2) . . ?
C5 C6 H6 119.2 . . ?
C1 C6 H6 119.2 . . ?
O5 C7 H7A 109.5 . . ?
O5 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
O5 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O4 C8 H8A 109.5 . . ?
O4 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
O4 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
C10 C9 C14 118.2(2) . . ?
C10 C9 P1 117.6(2) . . ?
C14 C9 P1 124.17(19) . . ?
C11 C10 C9 120.9(3) . . ?
C11 C10 H10 119.6 . . ?
C9 C10 H10 119.6 . . ?
C12 C11 C10 119.7(3) . . ?
C12 C11 H11 120.1 . . ?
C10 C11 H11 120.1 . . ?
C11 C12 C13 120.9(3) . . ?
C11 C12 H12 119.6 . . ?
C13 C12 H12 119.6 . . ?
C12 C13 C14 119.6(3) . . ?
C12 C13 H13 120.2 . . ?
C14 C13 H13 120.2 . . ?
C13 C14 C9 120.7(3) . . ?
C13 C14 H14 119.6 . . ?
C9 C14 H14 119.6 . . ?
C20 C15 C16 119.1(3) . . ?
C20 C15 P1 123.8(2) . . ?
C16 C15 P1 116.9(2) . . ?
C17 C16 C15 120.7(3) . . ?
C17 C16 H16 119.7 . . ?
C15 C16 H16 119.7 . . ?
C18 C17 C16 120.1(4) . . ?
C18 C17 H17 120.0 . . ?
C16 C17 H17 120.0 . . ?
C17 C18 C19 120.7(4) . . ?
C17 C18 H18 119.6 . . ?
C19 C18 H18 119.6 . . ?
C18 C19 C20 119.7(4) . . ?
C18 C19 H19 120.2 . . ?
C20 C19 H19 120.2 . . ?
C15 C20 C19 119.7(4) . . ?
C15 C20 H20 120.1 . . ?
C19 C20 H20 120.1 . . ?
C26 C21 C22 119.8(3) . . ?
C26 C21 S1 120.0(2) . . ?
C22 C21 S1 120.2(2) . . ?
C21 C22 C23 119.6(3) . . ?
C21 C22 H22 120.2 . . ?
C23 C22 H22 120.2 . . ?
C24 C23 C22 121.6(3) . . ?
C24 C23 H23 119.2 . . ?
C22 C23 H23 119.2 . . ?
C25 C24 C23 117.6(3) . . ?
C25 C24 C27 121.3(3) . . ?
C23 C24 C27 121.1(3) . . ?
C24 C25 C26 122.2(3) . . ?
C24 C25 H25 118.9 . . ?
C26 C25 H25 118.9 . . ?
C21 C26 C25 119.2(3) . . ?
C21 C26 H26 120.4 . . ?
C25 C26 H26 120.4 . . ?
C24 C27 H27A 109.5 . . ?
C24 C27 H27B 109.5 . . ?
H27A C27 H27B 109.5 . . ?
C24 C27 H27C 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 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
O2 S1 N1 C2 176.17(19) . . . . ?
O3 S1 N1 C2 47.1(2) . . . . ?
C21 S1 N1 C2 -68.9(2) . . . . ?
O1 P1 C1 C2 22.2(2) . . . . ?
C9 P1 C1 C2 -102.1(2) . . . . ?
C15 P1 C1 C2 144.2(2) . . . . ?
O1 P1 C1 C6 -161.70(18) . . . . ?
C9 P1 C1 C6 74.1(2) . . . . ?
C15 P1 C1 C6 -39.7(2) . . . . ?
C6 C1 C2 C3 -1.8(3) . . . . ?
P1 C1 C2 C3 174.41(18) . . . . ?
C6 C1 C2 N1 171.3(2) . . . . ?
P1 C1 C2 N1 -12.5(3) . . . . ?
S1 N1 C2 C1 126.3(2) . . . . ?
S1 N1 C2 C3 -60.6(3) . . . . ?
C1 C2 C3 C4 -0.4(4) . . . . ?
N1 C2 C3 C4 -173.5(2) . . . . ?
C8 O4 C4 C3 -2.5(5) . . . . ?
C8 O4 C4 C5 175.8(3) . . . . ?
C2 C3 C4 O4 -179.6(2) . . . . ?
C2 C3 C4 C5 2.2(4) . . . . ?
C7 O5 C5 C6 0.6(4) . . . . ?
C7 O5 C5 C4 -179.5(3) . . . . ?
O4 C4 C5 O5 0.1(4) . . . . ?
C3 C4 C5 O5 178.4(2) . . . . ?
O4 C4 C5 C6 179.9(2) . . . . ?
C3 C4 C5 C6 -1.7(4) . . . . ?
O5 C5 C6 C1 179.3(2) . . . . ?
C4 C5 C6 C1 -0.6(4) . . . . ?
C2 C1 C6 C5 2.3(4) . . . . ?
P1 C1 C6 C5 -174.0(2) . . . . ?
O1 P1 C9 C10 39.0(2) . . . . ?
C1 P1 C9 C10 162.5(2) . . . . ?
C15 P1 C9 C10 -82.2(2) . . . . ?
O1 P1 C9 C14 -141.9(2) . . . . ?
C1 P1 C9 C14 -18.3(2) . . . . ?
C15 P1 C9 C14 97.0(2) . . . . ?
C14 C9 C10 C11 0.1(4) . . . . ?
P1 C9 C10 C11 179.3(2) . . . . ?
C9 C10 C11 C12 -0.5(5) . . . . ?
C10 C11 C12 C13 0.1(5) . . . . ?
C11 C12 C13 C14 0.6(5) . . . . ?
C12 C13 C14 C9 -0.9(5) . . . . ?
C10 C9 C14 C13 0.6(4) . . . . ?
P1 C9 C14 C13 -178.6(2) . . . . ?
O1 P1 C15 C20 -147.3(3) . . . . ?
C9 P1 C15 C20 -24.3(3) . . . . ?
C1 P1 C15 C20 89.7(3) . . . . ?
O1 P1 C15 C16 26.9(3) . . . . ?
C9 P1 C15 C16 149.9(2) . . . . ?
C1 P1 C15 C16 -96.1(2) . . . . ?
C20 C15 C16 C17 -0.4(5) . . . . ?
P1 C15 C16 C17 -174.9(3) . . . . ?
C15 C16 C17 C18 -0.3(5) . . . . ?
C16 C17 C18 C19 -0.1(7) . . . . ?
C17 C18 C19 C20 1.2(7) . . . . ?
C16 C15 C20 C19 1.5(5) . . . . ?
P1 C15 C20 C19 175.7(3) . . . . ?
C18 C19 C20 C15 -1.9(6) . . . . ?
O2 S1 C21 C26 -157.9(2) . . . . ?
O3 S1 C21 C26 -26.7(2) . . . . ?
N1 S1 C21 C26 89.2(2) . . . . ?
O2 S1 C21 C22 23.1(3) . . . . ?
O3 S1 C21 C22 154.2(2) . . . . ?
N1 S1 C21 C22 -89.9(2) . . . . ?
C26 C21 C22 C23 0.3(5) . . . . ?
S1 C21 C22 C23 179.3(3) . . . . ?
C21 C22 C23 C24 0.8(6) . . . . ?
C22 C23 C24 C25 -1.6(5) . . . . ?
C22 C23 C24 C27 178.0(3) . . . . ?
C23 C24 C25 C26 1.4(5) . . . . ?
C27 C24 C25 C26 -178.2(3) . . . . ?
C22 C21 C26 C25 -0.5(4) . . . . ?
S1 C21 C26 C25 -179.6(2) . . . . ?
C24 C25 C26 C21 -0.3(5) . . . . ?

_refine_diff_density_max         0.308
_refine_diff_density_min         -0.521
_refine_diff_density_rms         0.109

####################################################################### 
# 
# 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_3bh
_database_code_depnum_ccdc_archive 'CCDC 1903626'
loop_
_audit_author_name
_audit_author_address
'Jian-Jun Liu'
;Qujing Normal University
China
;
_audit_update_record             
;
2019-03-16 deposited with the CCDC.	2019-05-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C22 H20 N O4 P S3'
_chemical_formula_sum            'C22 H20 N O4 P S3'
_chemical_formula_weight         489.54

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

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

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

_cell_length_a                   10.3307(12)
_cell_length_b                   17.782(2)
_cell_length_c                   12.0772(14)
_cell_angle_alpha                90
_cell_angle_beta                 100.953(2)
_cell_angle_gamma                90
_cell_volume                     2178.2(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    13663
_cell_measurement_theta_min      2.064
_cell_measurement_theta_max      28.441

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.493
_exptl_crystal_F_000             1016
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_absorpt_coefficient_mu    0.445
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9364
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   '(SADABS; Bruker, 2004)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      293(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13663
_diffrn_reflns_av_unetI/netI     0.0336
_diffrn_reflns_av_R_equivalents  0.0261
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         2.064
_diffrn_reflns_theta_max         28.441
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             5386
_reflns_number_gt                4545
_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       ?
_computing_cell_refinement       ?
_computing_data_reduction        ?
_computing_structure_solution    ?
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_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)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         5386
_refine_ls_number_parameters     282
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0503
_refine_ls_R_factor_gt           0.0415
_refine_ls_wR_factor_ref         0.1431
_refine_ls_wR_factor_gt          0.1330
_refine_ls_goodness_of_fit_ref   1.074
_refine_ls_restrained_S_all      1.074
_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
S1 S 0.18753(5) 0.37902(3) 0.06529(4) 0.01560(13) Uani 1 1 d . . . . .
S2 S 0.02289(6) 0.16957(3) 0.40001(5) 0.02955(16) Uani 1 1 d . . . . .
S3 S 0.15305(5) 0.42232(3) 0.60288(4) 0.02288(15) Uani 1 1 d . . . . .
P1 P 0.17822(5) 0.31800(3) 0.40548(4) 0.01356(13) Uani 1 1 d . . . . .
O1 O 0.31659(14) 0.40368(8) 0.05625(12) 0.0217(3) Uani 1 1 d . . . . .
O2 O 0.07695(14) 0.40011(8) -0.01953(11) 0.0201(3) Uani 1 1 d . . . . .
O3 O -0.31238(13) 0.36832(9) 0.33014(12) 0.0210(3) Uani 1 1 d . . . . .
O4 O 0.30250(13) 0.34637(8) 0.37615(11) 0.0183(3) Uani 1 1 d . . . . .
N1 N 0.16340(15) 0.41280(9) 0.18621(13) 0.0148(3) Uani 1 1 d . . . . .
H1 H 0.2263 0.4384 0.2295 0.018 Uiso 1 1 d R U . . .
C1 C 0.1889(2) 0.04134(12) 0.10102(19) 0.0286(5) Uani 1 1 d . . . . .
H1A H 0.1637 0.0220 0.0258 0.043 Uiso 1 1 calc R U . . .
H1B H 0.1275 0.0242 0.1461 0.043 Uiso 1 1 calc R U . . .
H1C H 0.2757 0.0239 0.1334 0.043 Uiso 1 1 calc R U . . .
C2 C 0.1883(2) 0.12552(11) 0.09757(16) 0.0198(4) Uani 1 1 d . . . . .
C3 C 0.0714(2) 0.16486(12) 0.07182(18) 0.0227(4) Uani 1 1 d . . . . .
H3 H -0.0080 0.1387 0.0610 0.027 Uiso 1 1 calc R U . . .
C4 C 0.06963(19) 0.24191(12) 0.06179(17) 0.0208(4) Uani 1 1 d . . . . .
H4 H -0.0101 0.2676 0.0444 0.025 Uiso 1 1 calc R U . . .
C5 C 0.18837(19) 0.28098(11) 0.07794(15) 0.0154(4) Uani 1 1 d . . . . .
C6 C 0.30670(19) 0.24289(12) 0.10674(16) 0.0184(4) Uani 1 1 d . . . . .
H6 H 0.3860 0.2692 0.1196 0.022 Uiso 1 1 calc R U . . .
C7 C 0.3062(2) 0.16594(12) 0.11622(17) 0.0209(4) Uani 1 1 d . . . . .
H7 H 0.3858 0.1403 0.1354 0.025 Uiso 1 1 calc R U . . .
C8 C 0.04081(18) 0.40063(10) 0.22127(15) 0.0135(4) Uani 1 1 d . . . . .
C9 C -0.07350(19) 0.43140(11) 0.15945(16) 0.0165(4) Uani 1 1 d . . . . .
H9 H -0.0696 0.4594 0.0951 0.020 Uiso 1 1 calc R U . . .
C10 C -0.19415(19) 0.42098(11) 0.19236(16) 0.0172(4) Uani 1 1 d . . . . .
H10 H -0.2707 0.4404 0.1487 0.021 Uiso 1 1 calc R U . . .
C11 C -0.20031(18) 0.38185(11) 0.28972(16) 0.0159(4) Uani 1 1 d . . . . .
C12 C -0.08568(18) 0.35285(11) 0.35432(15) 0.0158(4) Uani 1 1 d . . . . .
H12 H -0.0897 0.3276 0.4210 0.019 Uiso 1 1 calc R U . . .
C13 C 0.03503(18) 0.36094(10) 0.32079(15) 0.0140(4) Uani 1 1 d . . . . .
C14 C -0.4312(2) 0.40207(14) 0.27262(19) 0.0273(5) Uani 1 1 d . . . . .
H14A H -0.4514 0.3836 0.1966 0.041 Uiso 1 1 calc R U . . .
H14B H -0.4205 0.4557 0.2717 0.041 Uiso 1 1 calc R U . . .
H14C H -0.5019 0.3897 0.3107 0.041 Uiso 1 1 calc R U . . .
C15 C 0.16625(18) 0.33404(11) 0.54848(16) 0.0157(4) Uani 1 1 d . . . . .
C16 C 0.1780(2) 0.27990(12) 0.63260(16) 0.0198(4) Uani 1 1 d . . . . .
H16 H 0.1886 0.2288 0.6207 0.024 Uiso 1 1 calc R U . . .
C17 C 0.1719(2) 0.31227(12) 0.73941(17) 0.0239(4) Uani 1 1 d . . . . .
H17 H 0.1761 0.2843 0.8051 0.029 Uiso 1 1 calc R U . . .
C18 C 0.1594(2) 0.38746(12) 0.73518(17) 0.0227(4) Uani 1 1 d . . . . .
H18 H 0.1547 0.4172 0.7976 0.027 Uiso 1 1 calc R U . . .
C19 C 0.16189(19) 0.21902(11) 0.39018(16) 0.0176(4) Uani 1 1 d . . . . .
C20 C 0.2664(2) 0.16970(11) 0.38356(15) 0.0164(4) Uani 1 1 d . . . . .
H20 H 0.3513 0.1852 0.3793 0.020 Uiso 1 1 calc R U . . .
C21 C 0.2277(3) 0.09517(13) 0.38412(18) 0.0316(5) Uani 1 1 d . . . . .
H21 H 0.2839 0.0551 0.3783 0.038 Uiso 1 1 calc R U . . .
C22 C 0.1012(3) 0.08614(12) 0.39378(19) 0.0333(6) Uani 1 1 d . . . . .
H22 H 0.0612 0.0395 0.3967 0.040 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
S1 O1 1.4272(14) . ?
S1 O2 1.4320(14) . ?
S1 N1 1.6413(16) . ?
S1 C5 1.750(2) . ?
S2 C22 1.699(3) . ?
S2 C19 1.707(2) . ?
S3 C18 1.703(2) . ?
S3 C15 1.7172(19) . ?
P1 O4 1.4836(14) . ?
P1 C19 1.774(2) . ?
P1 C15 1.7777(19) . ?
P1 C13 1.8007(19) . ?
O3 C11 1.361(2) . ?
O3 C14 1.423(2) . ?
N1 C8 1.426(2) . ?
N1 H1 0.8800 . ?
C1 C2 1.498(3) . ?
C1 H1A 0.9600 . ?
C1 H1B 0.9600 . ?
C1 H1C 0.9600 . ?
C2 C3 1.380(3) . ?
C2 C7 1.395(3) . ?
C3 C4 1.375(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.391(3) . ?
C4 H4 0.9300 . ?
C5 C6 1.383(3) . ?
C6 C7 1.373(3) . ?
C6 H6 0.9300 . ?
C7 H7 0.9300 . ?
C8 C9 1.384(3) . ?
C8 C13 1.405(3) . ?
C9 C10 1.391(3) . ?
C9 H9 0.9300 . ?
C10 C11 1.378(3) . ?
C10 H10 0.9300 . ?
C11 C12 1.388(3) . ?
C12 C13 1.390(2) . ?
C12 H12 0.9300 . ?
C14 H14A 0.9600 . ?
C14 H14B 0.9600 . ?
C14 H14C 0.9600 . ?
C15 C16 1.388(3) . ?
C16 C17 1.425(3) . ?
C16 H16 0.9300 . ?
C17 C18 1.343(3) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
C19 C20 1.405(3) . ?
C20 C21 1.385(3) . ?
C20 H20 0.9300 . ?
C21 C22 1.343(4) . ?
C21 H21 0.9300 . ?
C22 H22 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 S1 O2 119.65(9) . . ?
O1 S1 N1 104.93(8) . . ?
O2 S1 N1 107.77(8) . . ?
O1 S1 C5 108.88(9) . . ?
O2 S1 C5 108.27(9) . . ?
N1 S1 C5 106.62(8) . . ?
C22 S2 C19 91.87(12) . . ?
C18 S3 C15 91.98(10) . . ?
O4 P1 C19 112.45(9) . . ?
O4 P1 C15 113.61(9) . . ?
C19 P1 C15 103.74(9) . . ?
O4 P1 C13 112.02(8) . . ?
C19 P1 C13 108.05(9) . . ?
C15 P1 C13 106.41(9) . . ?
C11 O3 C14 117.66(16) . . ?
C8 N1 S1 120.14(13) . . ?
C8 N1 H1 120.0 . . ?
S1 N1 H1 119.9 . . ?
C2 C1 H1A 109.5 . . ?
C2 C1 H1B 109.5 . . ?
H1A C1 H1B 109.5 . . ?
C2 C1 H1C 109.5 . . ?
H1A C1 H1C 109.5 . . ?
H1B C1 H1C 109.5 . . ?
C3 C2 C7 118.39(19) . . ?
C3 C2 C1 120.8(2) . . ?
C7 C2 C1 120.79(19) . . ?
C4 C3 C2 121.4(2) . . ?
C4 C3 H3 119.3 . . ?
C2 C3 H3 119.3 . . ?
C3 C4 C5 119.27(19) . . ?
C3 C4 H4 120.4 . . ?
C5 C4 H4 120.4 . . ?
C6 C5 C4 120.30(18) . . ?
C6 C5 S1 119.96(15) . . ?
C4 C5 S1 119.72(15) . . ?
C7 C6 C5 119.46(19) . . ?
C7 C6 H6 120.3 . . ?
C5 C6 H6 120.3 . . ?
C6 C7 C2 121.12(19) . . ?
C6 C7 H7 119.4 . . ?
C2 C7 H7 119.4 . . ?
C9 C8 C13 119.30(16) . . ?
C9 C8 N1 119.64(16) . . ?
C13 C8 N1 120.99(16) . . ?
C8 C9 C10 120.82(17) . . ?
C8 C9 H9 119.6 . . ?
C10 C9 H9 119.6 . . ?
C11 C10 C9 120.02(17) . . ?
C11 C10 H10 120.0 . . ?
C9 C10 H10 120.0 . . ?
O3 C11 C10 125.15(17) . . ?
O3 C11 C12 115.21(17) . . ?
C10 C11 C12 119.63(17) . . ?
C11 C12 C13 120.98(17) . . ?
C11 C12 H12 119.5 . . ?
C13 C12 H12 119.5 . . ?
C12 C13 C8 119.19(17) . . ?
C12 C13 P1 118.45(14) . . ?
C8 C13 P1 122.35(14) . . ?
O3 C14 H14A 109.5 . . ?
O3 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
O3 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
C16 C15 S3 110.87(14) . . ?
C16 C15 P1 125.96(15) . . ?
S3 C15 P1 122.93(11) . . ?
C15 C16 C17 111.70(18) . . ?
C15 C16 H16 124.2 . . ?
C17 C16 H16 124.2 . . ?
C18 C17 C16 112.84(18) . . ?
C18 C17 H17 123.6 . . ?
C16 C17 H17 123.6 . . ?
C17 C18 S3 112.59(16) . . ?
C17 C18 H18 123.7 . . ?
S3 C18 H18 123.7 . . ?
C20 C19 S2 110.38(15) . . ?
C20 C19 P1 124.48(15) . . ?
S2 C19 P1 124.63(12) . . ?
C21 C20 C19 111.79(19) . . ?
C21 C20 H20 124.1 . . ?
C19 C20 H20 124.1 . . ?
C22 C21 C20 113.7(2) . . ?
C22 C21 H21 123.2 . . ?
C20 C21 H21 123.2 . . ?
C21 C22 S2 112.27(17) . . ?
C21 C22 H22 123.9 . . ?
S2 C22 H22 123.9 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 S1 N1 C8 178.13(14) . . . . ?
O2 S1 N1 C8 49.59(16) . . . . ?
C5 S1 N1 C8 -66.46(16) . . . . ?
C7 C2 C3 C4 1.6(3) . . . . ?
C1 C2 C3 C4 -176.10(19) . . . . ?
C2 C3 C4 C5 0.0(3) . . . . ?
C3 C4 C5 C6 -1.7(3) . . . . ?
C3 C4 C5 S1 179.94(15) . . . . ?
O1 S1 C5 C6 16.56(18) . . . . ?
O2 S1 C5 C6 148.12(15) . . . . ?
N1 S1 C5 C6 -96.16(16) . . . . ?
O1 S1 C5 C4 -165.10(15) . . . . ?
O2 S1 C5 C4 -33.54(18) . . . . ?
N1 S1 C5 C4 82.18(17) . . . . ?
C4 C5 C6 C7 1.8(3) . . . . ?
S1 C5 C6 C7 -179.88(15) . . . . ?
C5 C6 C7 C2 -0.2(3) . . . . ?
C3 C2 C7 C6 -1.5(3) . . . . ?
C1 C2 C7 C6 176.17(18) . . . . ?
S1 N1 C8 C9 -64.4(2) . . . . ?
S1 N1 C8 C13 118.80(17) . . . . ?
C13 C8 C9 C10 -2.5(3) . . . . ?
N1 C8 C9 C10 -179.40(17) . . . . ?
C8 C9 C10 C11 2.3(3) . . . . ?
C14 O3 C11 C10 -5.2(3) . . . . ?
C14 O3 C11 C12 174.83(18) . . . . ?
C9 C10 C11 O3 179.90(18) . . . . ?
C9 C10 C11 C12 -0.2(3) . . . . ?
O3 C11 C12 C13 178.23(17) . . . . ?
C10 C11 C12 C13 -1.7(3) . . . . ?
C11 C12 C13 C8 1.5(3) . . . . ?
C11 C12 C13 P1 -177.12(15) . . . . ?
C9 C8 C13 C12 0.6(3) . . . . ?
N1 C8 C13 C12 177.48(17) . . . . ?
C9 C8 C13 P1 179.16(14) . . . . ?
N1 C8 C13 P1 -4.0(2) . . . . ?
O4 P1 C13 C12 -166.09(14) . . . . ?
C19 P1 C13 C12 69.50(17) . . . . ?
C15 P1 C13 C12 -41.38(17) . . . . ?
O4 P1 C13 C8 15.37(19) . . . . ?
C19 P1 C13 C8 -109.04(16) . . . . ?
C15 P1 C13 C8 140.08(16) . . . . ?
C18 S3 C15 C16 -1.25(16) . . . . ?
C18 S3 C15 P1 -175.90(13) . . . . ?
O4 P1 C15 C16 -106.94(18) . . . . ?
C19 P1 C15 C16 15.5(2) . . . . ?
C13 P1 C15 C16 129.33(17) . . . . ?
O4 P1 C15 S3 66.88(15) . . . . ?
C19 P1 C15 S3 -170.71(12) . . . . ?
C13 P1 C15 S3 -56.85(14) . . . . ?
S3 C15 C16 C17 1.7(2) . . . . ?
P1 C15 C16 C17 176.19(15) . . . . ?
C15 C16 C17 C18 -1.5(3) . . . . ?
C16 C17 C18 S3 0.5(3) . . . . ?
C15 S3 C18 C17 0.42(18) . . . . ?
C22 S2 C19 C20 -0.66(16) . . . . ?
C22 S2 C19 P1 -172.73(14) . . . . ?
O4 P1 C19 C20 17.4(2) . . . . ?
C15 P1 C19 C20 -105.73(17) . . . . ?
C13 P1 C19 C20 141.60(16) . . . . ?
O4 P1 C19 S2 -171.57(11) . . . . ?
C15 P1 C19 S2 65.25(15) . . . . ?
C13 P1 C19 S2 -47.42(15) . . . . ?
S2 C19 C20 C21 1.4(2) . . . . ?
P1 C19 C20 C21 173.50(15) . . . . ?
C19 C20 C21 C22 -1.7(3) . . . . ?
C20 C21 C22 S2 1.2(3) . . . . ?
C19 S2 C22 C21 -0.27(19) . . . . ?

_refine_diff_density_max         0.783
_refine_diff_density_min         -0.734
_refine_diff_density_rms         0.080

