# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# 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_q
_database_code_depnum_ccdc_archive 'CCDC 2184646'
loop_
_audit_author_name
_audit_author_address
'Guo Shengmei'
;NanChang University
China
;
_audit_update_record             
;
2022-07-07 deposited with the CCDC.	2022-11-02 downloaded from the CCDC.
;
_audit_creation_date             2022-07-07
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C18 H15 O P S'
_chemical_formula_sum            'C18 H15 O P S'
_chemical_formula_weight         310.33
_chemical_melting_point          ?
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'
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'

_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      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.190(2)
_cell_length_b                   8.426(3)
_cell_length_c                   16.517(5)
_cell_angle_alpha                100.248(5)
_cell_angle_beta                 96.034(5)
_cell_angle_gamma                108.478(5)
_cell_volume                     791.9(4)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    2073
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      54.426
_cell_measurement_theta_min      5.299
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.301
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6883
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0556 before and 0.0258 after correction.
The Ratio of minimum to maximum transmission is 0.9231.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.302
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             324
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0181
_diffrn_reflns_av_unetI/netI     0.0341
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.948
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            4768
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.948
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.463
_diffrn_reflns_theta_min         2.545
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.948
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2711
_reflns_number_total             3428
_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       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.239
_refine_diff_density_min         -0.329
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         3428
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0581
_refine_ls_R_factor_gt           0.0429
_refine_ls_restrained_S_all      1.017
_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)+(0.0479P)²+0.3470P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1047
_refine_ls_wR_factor_ref         0.1128
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C8(H8), C12(H12), C14(H14), C10(H10), C11(H11), C9(H9), C1(H1), C16(H16),
 C15(H15), C5(H5), C18(H18), C3(H3), C4(H4), C2(H2), C17(H17)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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 0.58564(9) 0.34270(6) 0.77191(3) 0.03438(15) Uani 1 1 d . . . . .
S1 S 0.66162(11) 0.16398(7) 0.68575(3) 0.04897(18) Uani 1 1 d . . . . .
O1 O 0.3386(2) 0.3269(2) 0.76380(10) 0.0500(4) Uani 1 1 d . . . . .
C7 C 0.7658(3) 0.5555(2) 0.76721(11) 0.0330(4) Uani 1 1 d . . . . .
C13 C 0.6913(4) 0.2980(2) 0.86833(12) 0.0376(4) Uani 1 1 d . . . . .
C6 C 0.5745(4) 0.2159(3) 0.59026(12) 0.0417(5) Uani 1 1 d . . . . .
C8 C 0.9807(4) 0.5944(3) 0.74188(13) 0.0438(5) Uani 1 1 d . . . . .
H8 H 1.041556 0.508247 0.725762 0.053 Uiso 1 1 calc R U . . .
C12 C 0.6795(4) 0.6860(3) 0.79253(13) 0.0430(5) Uani 1 1 d . . . . .
H12 H 0.536511 0.660446 0.809743 0.052 Uiso 1 1 calc R U . . .
C14 C 0.9175(4) 0.3127(3) 0.89326(14) 0.0508(6) Uani 1 1 d . . . . .
H14 H 1.026134 0.344464 0.858965 0.061 Uiso 1 1 calc R U . . .
C10 C 1.0141(5) 0.8926(3) 0.76595(16) 0.0596(7) Uani 1 1 d . . . . .
H10 H 1.096232 1.005421 0.764798 0.071 Uiso 1 1 calc R U . . .
C11 C 0.8048(5) 0.8536(3) 0.79229(15) 0.0560(6) Uani 1 1 d . . . . .
H11 H 0.746847 0.940572 0.810137 0.067 Uiso 1 1 calc R U . . .
C9 C 1.1032(4) 0.7642(3) 0.74105(14) 0.0551(6) Uani 1 1 d . . . . .
H9 H 1.245895 0.791279 0.723602 0.066 Uiso 1 1 calc R U . . .
C1 C 0.7403(5) 0.2868(4) 0.54534(16) 0.0647(7) Uani 1 1 d . . . . .
H1 H 0.896012 0.312699 0.566132 0.078 Uiso 1 1 calc R U . . .
C16 C 0.8234(5) 0.2319(4) 1.02051(16) 0.0677(8) Uani 1 1 d . . . . .
H16 H 0.868575 0.211056 1.071935 0.081 Uiso 1 1 calc R U . . .
C15 C 0.9825(5) 0.2798(4) 0.96994(16) 0.0648(7) Uani 1 1 d . . . . .
H15 H 1.135469 0.290393 0.987004 0.078 Uiso 1 1 calc R U . . .
C5 C 0.3449(5) 0.1771(4) 0.55875(16) 0.0649(7) Uani 1 1 d . . . . .
H5 H 0.231535 0.128923 0.588646 0.078 Uiso 1 1 calc R U . . .
C18 C 0.5324(5) 0.2468(4) 0.91945(16) 0.0701(8) Uani 1 1 d . . . . .
H18 H 0.378301 0.233457 0.902552 0.084 Uiso 1 1 calc R U . . .
C3 C 0.4476(7) 0.2803(4) 0.43794(17) 0.0797(9) Uani 1 1 d . . . . .
H3 H 0.404790 0.301591 0.386367 0.096 Uiso 1 1 calc R U . . .
C4 C 0.2836(6) 0.2104(5) 0.48201(18) 0.0824(9) Uani 1 1 d . . . . .
H4 H 0.128365 0.184559 0.460557 0.099 Uiso 1 1 calc R U . . .
C2 C 0.6748(7) 0.3193(4) 0.46929(18) 0.0846(10) Uani 1 1 d . . . . .
H2 H 0.787121 0.368385 0.439202 0.101 Uiso 1 1 calc R U . . .
C17 C 0.6004(6) 0.2150(5) 0.99570(18) 0.0867(10) Uani 1 1 d . . . . .
H17 H 0.492364 0.181934 1.030041 0.104 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 S1 2.0836(9) . ?
P1 O1 1.4817(16) . ?
P1 C7 1.807(2) . ?
P1 C13 1.804(2) . ?
S1 C6 1.785(2) . ?
C7 C8 1.393(3) . ?
C7 C12 1.387(3) . ?
C13 C14 1.377(3) . ?
C13 C18 1.380(3) . ?
C6 C1 1.375(3) . ?
C6 C5 1.374(3) . ?
C8 H8 0.9300 . ?
C8 C9 1.394(3) . ?
C12 H12 0.9300 . ?
C12 C11 1.380(3) . ?
C14 H14 0.9300 . ?
C14 C15 1.390(3) . ?
C10 H10 0.9300 . ?
C10 C11 1.369(4) . ?
C10 C9 1.383(4) . ?
C11 H11 0.9300 . ?
C9 H9 0.9300 . ?
C1 H1 0.9300 . ?
C1 C2 1.380(4) . ?
C16 H16 0.9300 . ?
C16 C15 1.368(4) . ?
C16 C17 1.352(4) . ?
C15 H15 0.9300 . ?
C5 H5 0.9300 . ?
C5 C4 1.387(4) . ?
C18 H18 0.9300 . ?
C18 C17 1.384(4) . ?
C3 H3 0.9300 . ?
C3 C4 1.355(4) . ?
C3 C2 1.359(5) . ?
C4 H4 0.9300 . ?
C2 H2 0.9300 . ?
C17 H17 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 P1 S1 115.52(7) . . ?
O1 P1 C7 111.30(9) . . ?
O1 P1 C13 112.54(9) . . ?
C7 P1 S1 108.52(7) . . ?
C13 P1 S1 100.32(7) . . ?
C13 P1 C7 107.90(9) . . ?
C6 S1 P1 100.78(7) . . ?
C8 C7 P1 124.58(15) . . ?
C12 C7 P1 115.70(15) . . ?
C12 C7 C8 119.71(19) . . ?
C14 C13 P1 124.20(16) . . ?
C14 C13 C18 119.0(2) . . ?
C18 C13 P1 116.77(18) . . ?
C1 C6 S1 119.04(19) . . ?
C5 C6 S1 121.18(18) . . ?
C5 C6 C1 119.7(2) . . ?
C7 C8 H8 120.5 . . ?
C7 C8 C9 119.0(2) . . ?
C9 C8 H8 120.5 . . ?
C7 C12 H12 119.8 . . ?
C11 C12 C7 120.3(2) . . ?
C11 C12 H12 119.8 . . ?
C13 C14 H14 120.2 . . ?
C13 C14 C15 119.7(2) . . ?
C15 C14 H14 120.2 . . ?
C11 C10 H10 120.0 . . ?
C11 C10 C9 120.0(2) . . ?
C9 C10 H10 120.0 . . ?
C12 C11 H11 119.8 . . ?
C10 C11 C12 120.4(2) . . ?
C10 C11 H11 119.8 . . ?
C8 C9 H9 119.7 . . ?
C10 C9 C8 120.5(2) . . ?
C10 C9 H9 119.7 . . ?
C6 C1 H1 120.1 . . ?
C6 C1 C2 119.7(3) . . ?
C2 C1 H1 120.1 . . ?
C15 C16 H16 120.0 . . ?
C17 C16 H16 120.0 . . ?
C17 C16 C15 120.0(2) . . ?
C14 C15 H15 119.7 . . ?
C16 C15 C14 120.5(3) . . ?
C16 C15 H15 119.7 . . ?
C6 C5 H5 120.3 . . ?
C6 C5 C4 119.5(3) . . ?
C4 C5 H5 120.3 . . ?
C13 C18 H18 119.8 . . ?
C13 C18 C17 120.5(3) . . ?
C17 C18 H18 119.8 . . ?
C4 C3 H3 120.1 . . ?
C4 C3 C2 119.8(3) . . ?
C2 C3 H3 120.1 . . ?
C5 C4 H4 119.7 . . ?
C3 C4 C5 120.7(3) . . ?
C3 C4 H4 119.7 . . ?
C1 C2 H2 119.7 . . ?
C3 C2 C1 120.6(3) . . ?
C3 C2 H2 119.7 . . ?
C16 C17 C18 120.3(3) . . ?
C16 C17 H17 119.8 . . ?
C18 C17 H17 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 S1 C6 C1 112.02(19) . . . . ?
P1 S1 C6 C5 -71.8(2) . . . . ?
P1 C7 C8 C9 -179.96(16) . . . . ?
P1 C7 C12 C11 179.22(16) . . . . ?
P1 C13 C14 C15 178.21(19) . . . . ?
P1 C13 C18 C17 -178.0(3) . . . . ?
S1 P1 C7 C8 -26.50(19) . . . . ?
S1 P1 C7 C12 154.69(14) . . . . ?
S1 P1 C13 C14 60.33(19) . . . . ?
S1 P1 C13 C18 -119.9(2) . . . . ?
S1 C6 C1 C2 176.6(2) . . . . ?
S1 C6 C5 C4 -176.3(2) . . . . ?
O1 P1 C7 C8 -154.69(17) . . . . ?
O1 P1 C7 C12 26.50(18) . . . . ?
O1 P1 C13 C14 -176.33(18) . . . . ?
O1 P1 C13 C18 3.4(2) . . . . ?
C7 P1 C13 C14 -53.1(2) . . . . ?
C7 P1 C13 C18 126.6(2) . . . . ?
C7 C8 C9 C10 0.8(3) . . . . ?
C7 C12 C11 C10 0.9(3) . . . . ?
C13 P1 C7 C8 81.37(19) . . . . ?
C13 P1 C7 C12 -97.45(17) . . . . ?
C13 C14 C15 C16 0.4(4) . . . . ?
C13 C18 C17 C16 -0.8(5) . . . . ?
C6 C1 C2 C3 -0.7(5) . . . . ?
C6 C5 C4 C3 0.1(5) . . . . ?
C8 C7 C12 C11 0.3(3) . . . . ?
C12 C7 C8 C9 -1.2(3) . . . . ?
C14 C13 C18 C17 1.7(4) . . . . ?
C11 C10 C9 C8 0.5(4) . . . . ?
C9 C10 C11 C12 -1.4(4) . . . . ?
C1 C6 C5 C4 -0.1(4) . . . . ?
C15 C16 C17 C18 -0.3(5) . . . . ?
C5 C6 C1 C2 0.4(4) . . . . ?
C18 C13 C14 C15 -1.5(4) . . . . ?
C4 C3 C2 C1 0.7(5) . . . . ?
C2 C3 C4 C5 -0.4(5) . . . . ?
C17 C16 C15 C14 0.5(5) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'

####################################################################### 
# 
# 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_q
_database_code_depnum_ccdc_archive 'CCDC 2184647'
loop_
_audit_author_name
_audit_author_address
'Guo Shengmei'
;NanChang University
China
;
_audit_update_record             
;
2022-07-07 deposited with the CCDC.	2022-11-15 downloaded from the CCDC.
;
_audit_creation_date             2022-07-07
_audit_creation_method           
;
Olex2 1.5-beta
(compiled 2022.04.07 svn.rca3783a0 for OlexSys, GUI svn.r6498)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H11 O2 P'
_chemical_formula_sum            'C12 H11 O2 P'
_chemical_formula_weight         218.18
_chemical_melting_point          ?
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'
P P 0.1023 0.0942 '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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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'

_cell_length_a                   11.482(3)
_cell_length_b                   6.0814(17)
_cell_length_c                   15.777(5)
_cell_angle_alpha                90
_cell_angle_beta                 99.883(5)
_cell_angle_gamma                90
_cell_volume                     1085.3(5)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2333
_cell_measurement_temperature    296.15
_cell_measurement_theta_max      54.523
_cell_measurement_theta_min      5.822
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.228
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_correction_T_min  0.6620
_exptl_absorpt_correction_type   ?
_exptl_absorpt_process_details   
;
SADABS-2014/5 (Bruker,2014/5) was used for absorption correction.
wR2(int) was 0.0934 before and 0.0405 after correction.
The Ratio of minimum to maximum transmission is 0.8879.
The λ/2 correction factor is 0.00150.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.335
_exptl_crystal_density_meas      .
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             456
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  ?
_diffrn_reflns_av_unetI/netI     0.0349
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2459
_diffrn_reflns_point_group_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.980
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.636
_diffrn_reflns_theta_min         1.800
_diffrn_ambient_temperature      296.15
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.993
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_source_current           30.0
_diffrn_source_power             1.5
_diffrn_source_voltage           50.0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2004
_reflns_number_total             2459
_reflns_special_details          
;
 _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. Completness statistics refer to single and
 composite reflections containing twin component 1 only.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.5-beta (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT  (Sheldrick, 2015)'
_refine_diff_density_max         0.724
_refine_diff_density_min         -0.347
_refine_diff_density_rms         0.111
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     138
_refine_ls_number_reflns         2459
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0841
_refine_ls_R_factor_gt           0.0705
_refine_ls_restrained_S_all      1.083
_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)+(0.1552P)²+1.7325P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2407
_refine_ls_wR_factor_ref         0.2568
_refine_special_details          
;
 Refined as a 2-component twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.941(2)
 0.059(2)
2. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
3.a Aromatic/amide H refined with riding coordinates:
 C5(H5), C12(H12), C8(H8), C1(H1A), C10(H10), C11(H11), C9(H9), C2(H2), C3(H3),
  C4(H4)
3.b Idealised tetrahedral OH refined as rotating group:
 O1(H1)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_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 0.83872(8) 0.60659(16) 0.24993(6) 0.0257(3) Uani 1 1 d . . . . .
O1 O 0.8839(3) 0.8462(5) 0.2492(2) 0.0427(8) Uani 1 1 d . . . . .
H1 H 0.955850 0.848069 0.264357 0.064 Uiso 1 1 calc R U . . .
O2 O 0.9022(3) 0.4362(5) 0.2065(2) 0.0413(8) Uani 1 1 d . . . . .
C6 C 0.6881(3) 0.6310(6) 0.1964(2) 0.0286(8) Uani 1 1 d . . . . .
C7 C 0.8371(3) 0.5332(7) 0.3605(2) 0.0285(8) Uani 1 1 d . . . . .
C5 C 0.6332(4) 0.4532(8) 0.1503(3) 0.0415(10) Uani 1 1 d . . . . .
H5 H 0.674325 0.322629 0.147081 0.050 Uiso 1 1 calc R U . . .
C12 C 0.8769(4) 0.3296(8) 0.3933(3) 0.0405(10) Uani 1 1 d . . . . .
H12 H 0.902748 0.225475 0.357568 0.049 Uiso 1 1 calc R U . . .
C8 C 0.7963(5) 0.6856(9) 0.4144(3) 0.0468(11) Uani 1 1 d . . . . .
H8 H 0.767919 0.821463 0.393047 0.056 Uiso 1 1 calc R U . . .
C1 C 0.6255(4) 0.8239(9) 0.2013(3) 0.0444(11) Uani 1 1 d . . . . .
H1A H 0.661855 0.943150 0.231998 0.053 Uiso 1 1 calc R U . . .
C10 C 0.8380(5) 0.4329(10) 0.5323(3) 0.0536(14) Uani 1 1 d . . . . .
H10 H 0.837991 0.398685 0.589754 0.064 Uiso 1 1 calc R U . . .
C11 C 0.8782(4) 0.2813(9) 0.4798(4) 0.0516(13) Uani 1 1 d . . . . .
H11 H 0.906389 0.146026 0.501925 0.062 Uiso 1 1 calc R U . . .
C9 C 0.7982(6) 0.6325(10) 0.5012(3) 0.0609(15) Uani 1 1 d . . . . .
H9 H 0.772057 0.734603 0.537640 0.073 Uiso 1 1 calc R U . . .
C2 C 0.5087(5) 0.8398(11) 0.1607(4) 0.0607(15) Uani 1 1 d . . . . .
H2 H 0.466524 0.968934 0.164509 0.073 Uiso 1 1 calc R U . . .
C3 C 0.4558(4) 0.6645(13) 0.1149(4) 0.0678(18) Uani 1 1 d . . . . .
H3 H 0.377609 0.675926 0.087390 0.081 Uiso 1 1 calc R U . . .
C4 C 0.5166(5) 0.4723(12) 0.1092(4) 0.0608(15) Uani 1 1 d . . . . .
H4 H 0.479672 0.354685 0.077828 0.073 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
P1 O1 1.547(3) . ?
P1 O2 1.499(3) . ?
P1 C6 1.796(4) . ?
P1 C7 1.805(4) . ?
O1 H1 0.8200 . ?
C6 C5 1.392(6) . ?
C6 C1 1.385(6) . ?
C7 C12 1.389(6) . ?
C7 C8 1.392(6) . ?
C5 H5 0.9300 . ?
C5 C4 1.389(7) . ?
C12 H12 0.9300 . ?
C12 C11 1.393(7) . ?
C8 H8 0.9300 . ?
C8 C9 1.403(7) . ?
C1 H1A 0.9300 . ?
C1 C2 1.387(7) . ?
C10 H10 0.9300 . ?
C10 C11 1.371(8) . ?
C10 C9 1.359(8) . ?
C11 H11 0.9300 . ?
C9 H9 0.9300 . ?
C2 H2 0.9300 . ?
C2 C3 1.370(9) . ?
C3 H3 0.9300 . ?
C3 C4 1.373(9) . ?
C4 H4 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 P1 C6 102.45(18) . . ?
O1 P1 C7 107.41(19) . . ?
O2 P1 O1 117.23(19) . . ?
O2 P1 C6 110.29(18) . . ?
O2 P1 C7 110.99(19) . . ?
C6 P1 C7 107.82(17) . . ?
P1 O1 H1 109.5 . . ?
C5 C6 P1 119.6(3) . . ?
C1 C6 P1 120.7(3) . . ?
C1 C6 C5 119.6(4) . . ?
C12 C7 P1 121.6(3) . . ?
C12 C7 C8 119.3(4) . . ?
C8 C7 P1 119.1(3) . . ?
C6 C5 H5 120.2 . . ?
C4 C5 C6 119.5(5) . . ?
C4 C5 H5 120.2 . . ?
C7 C12 H12 120.0 . . ?
C7 C12 C11 120.0(5) . . ?
C11 C12 H12 120.0 . . ?
C7 C8 H8 120.3 . . ?
C7 C8 C9 119.5(5) . . ?
C9 C8 H8 120.3 . . ?
C6 C1 H1A 119.9 . . ?
C6 C1 C2 120.2(5) . . ?
C2 C1 H1A 119.9 . . ?
C11 C10 H10 119.7 . . ?
C9 C10 H10 119.7 . . ?
C9 C10 C11 120.6(5) . . ?
C12 C11 H11 119.9 . . ?
C10 C11 C12 120.1(5) . . ?
C10 C11 H11 119.9 . . ?
C8 C9 H9 119.8 . . ?
C10 C9 C8 120.4(5) . . ?
C10 C9 H9 119.8 . . ?
C1 C2 H2 120.1 . . ?
C3 C2 C1 119.7(5) . . ?
C3 C2 H2 120.1 . . ?
C2 C3 H3 119.6 . . ?
C2 C3 C4 120.8(5) . . ?
C4 C3 H3 119.6 . . ?
C5 C4 H4 120.0 . . ?
C3 C4 C5 120.1(6) . . ?
C3 C4 H4 120.0 . . ?

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 C6 C5 C4 179.8(4) . . . . ?
P1 C6 C1 C2 -179.1(4) . . . . ?
P1 C7 C12 C11 177.8(3) . . . . ?
P1 C7 C8 C9 -178.0(4) . . . . ?
O1 P1 C6 C5 151.1(3) . . . . ?
O1 P1 C6 C1 -29.6(4) . . . . ?
O1 P1 C7 C12 -137.2(3) . . . . ?
O1 P1 C7 C8 42.0(4) . . . . ?
O2 P1 C6 C5 25.6(4) . . . . ?
O2 P1 C6 C1 -155.2(4) . . . . ?
O2 P1 C7 C12 -7.8(4) . . . . ?
O2 P1 C7 C8 171.3(3) . . . . ?
C6 P1 C7 C12 113.1(4) . . . . ?
C6 P1 C7 C8 -67.8(4) . . . . ?
C6 C5 C4 C3 -0.7(8) . . . . ?
C6 C1 C2 C3 -0.6(8) . . . . ?
C7 P1 C6 C5 -95.7(4) . . . . ?
C7 P1 C6 C1 83.5(4) . . . . ?
C7 C12 C11 C10 1.3(7) . . . . ?
C7 C8 C9 C10 -0.9(9) . . . . ?
C5 C6 C1 C2 0.1(7) . . . . ?
C12 C7 C8 C9 1.2(7) . . . . ?
C8 C7 C12 C11 -1.4(7) . . . . ?
C1 C6 C5 C4 0.6(7) . . . . ?
C1 C2 C3 C4 0.5(9) . . . . ?
C11 C10 C9 C8 0.8(9) . . . . ?
C9 C10 C11 C12 -1.0(8) . . . . ?
C2 C3 C4 C5 0.2(9) . . . . ?

_olex2_submission_special_instructions 'No special instructions were received'
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.941(2)
2 0.059(2)

