# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2023

####################################################################### 
# 
# 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_paj719a-1
_database_code_depnum_ccdc_archive 'CCDC 2296518'
loop_
_audit_author_name
_audit_author_address
'Geoffrey Letheux Olivier Perez'
;CRISMAT
France
;
_audit_update_record             
;
2023-09-21 deposited with the CCDC.	2023-11-15 downloaded from the CCDC.
;
_audit_creation_date             2020-06-10
_audit_creation_method           
;
Olex2 1.2-ac4
(compiled 2018.05.17 svn.r3504 for Rigaku Oxford Diffraction, GUI svn.r5492)
;
_shelx_SHELXL_version_number     2016/4
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H9 O3 P S2'
_chemical_formula_sum            'C12 H9 O3 P S2'
_chemical_formula_weight         296.28
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C12 H9 O3 P S2 '
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'
S S 0.3331 0.5567 '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           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   4.80963(5)
_cell_length_b                   10.61773(11)
_cell_length_c                   24.0170(2)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1226.48(2)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    14093
_cell_measurement_temperature    292.85(10)
_cell_measurement_theta_max      75.5300
_cell_measurement_theta_min      3.6500
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    5.158
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.536
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.23a (Rigaku Oxford Diffraction, 2018)
Numerical absorption correction based on gaussian integration over
			a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.605
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             608
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 0 1 0.0121
0 0 -1 0.0177
-1 -1 -2 0.0652
1 1 2 0.0468
0 1 -1 0.0164
0 -1 1 0.0107
0 1 0 0.0183
-1 1 -1 0.0603

_exptl_crystal_preparation       ?
_exptl_crystal_size_max          0.143
_exptl_crystal_size_mid          0.043
_exptl_crystal_size_min          0.027
loop_
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
0.0001 -0.0002 0.9997 -0.0524 -0.0341 0.0141
-0.0001 0.0002 -0.9997 0.0524 0.0341 -0.0141
-1.0001 -0.9993 -2.0019 0.0268 0.0467 -0.3705
1.0001 0.9993 2.0019 -0.0268 -0.0467 0.3705
-0.0000 1.0000 -0.9978 -0.0044 0.1494 0.0531
0.0000 -1.0000 0.9978 0.0044 -0.1494 -0.0531
0.0001 0.9997 0.0019 -0.0569 0.1153 0.0673
-0.9999 0.9999 -0.9984 -0.1394 0.2431 -0.2218

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0359
_diffrn_reflns_av_unetI/netI     0.0148
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            23440
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.890
_diffrn_reflns_theta_min         3.681
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      292.85(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'Eiger 1M'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     29.00 117.00   0.50    0.50    --   43.75  38.00 -30.00  176
  2  ω    100.00 171.00   0.50    2.00    --  110.00  85.00  -4.00  142
  3  ω     97.00 171.00   0.50    2.00    --  110.00  45.00 150.00  148
  4  ω     97.00 171.00   0.50    2.00    --  110.00  45.00  60.00  148
  5  ω     97.00 171.00   0.50    2.00    --  110.00  45.00 120.00  148
  6  ω     90.00 161.00   0.50    2.00    --  110.00  30.00  30.00  142
  7  ω     89.00 171.00   0.50    2.00    --  110.00  61.00 -60.00  164
  8  ω     97.00 171.00   0.50    2.00    --  110.00  45.00-180.00  148
  9  ω     90.00 171.00   0.50    2.00    --  110.00  30.00 -60.00  162
 10  ω     90.00 171.00   0.50    2.00    --  110.00  30.00   0.00  162
 11  ω     90.00 171.00   0.50    2.00    --  110.00  30.00-120.00  162
 12  ω     76.00 171.00   0.50    2.00    --  110.00  15.00 120.00  190
 13  ω     43.00 142.00   0.50    2.00    --  110.00 -85.00-123.00  198
 14  ω     34.00 129.00   0.50    2.00    --  110.00 -30.00 -60.00  190
 15  ω     46.00 139.00   0.50    2.00    --  110.00 -77.00-150.00  186
 16  ω     44.00 130.00   0.50    2.00    --  110.00 -61.00   0.00  172
 17  ω     38.00 106.00   0.50    2.00    --  110.00 -94.00  30.00  136
 18  ω     39.00 112.00   0.50    2.00    --  110.00-125.00 -30.00  146
 19  ω     38.00 123.00   0.50    2.00    --  110.00 -45.00  90.00  170
 20  ω     34.00 129.00   0.50    2.00    --  110.00 -30.00 150.00  190
 21  ω     39.00 112.00   0.50    2.00    --  110.00-125.00  60.00  146
 22  ω     38.00 106.00   0.50    2.00    --  110.00 -94.00-150.00  136
 23  ω     26.00 111.00   0.50    0.50    --   43.75  57.00-150.00  170
 24  ω     15.00 108.00   0.50    0.50    --   43.75  77.00  30.00  186
 25  ω     26.00 111.00   0.50    0.50    --   43.75  57.00  90.00  170
 26  ω     15.00 108.00   0.50    0.50    --   43.75  77.00   0.00  186
 27  ω     15.00 108.00   0.50    0.50    --   43.75  77.00 150.00  186
 28  ω     15.00 108.00   0.50    0.50    --   43.75  77.00  60.00  186
 29  ω     15.00 108.00   0.50    0.50    --   43.75  77.00 -90.00  186
 30  ω     15.00 108.00   0.50    0.50    --   43.75  77.00-150.00  186
 31  ω     15.00 108.00   0.50    0.50    --   43.75  77.00 -60.00  186
 32  ω     15.00 108.00   0.50    0.50    --   43.75  77.00 120.00  186
 33  ω    -21.00  31.00   0.50    0.50    --   -0.75 -85.00-123.00  104
 34  ω    -13.00  36.00   0.50    0.50    --   -0.75 -94.00-180.00   98
 35  ω    -21.00  76.00   0.50    0.50    --   43.75 -85.00-123.00  194
 36  ω     -2.00  83.00   0.50    0.50    --   43.75 -99.00  30.00  170
 37  ω     -2.00  83.00   0.50    0.50    --   43.75 -99.00  90.00  170
 38  ω    -21.00  72.00   0.50    0.50    --   43.75 -77.00 120.00  186
 39  ω    -33.00  43.00   0.50    0.50    --   -0.75  85.00  -4.00  152
 40  ω    -34.00  68.00   0.50    0.50    --   43.75 -19.00-150.00  204
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, Eiger 1M'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1349580000
_diffrn_orient_matrix_UB_12      -0.0567940000
_diffrn_orient_matrix_UB_13      -0.0524685000
_diffrn_orient_matrix_UB_21      -0.0937583000
_diffrn_orient_matrix_UB_22      0.1153528000
_diffrn_orient_matrix_UB_23      -0.0340747000
_diffrn_orient_matrix_UB_31      0.2749518000
_diffrn_orient_matrix_UB_32      0.0672567000
_diffrn_orient_matrix_UB_33      0.0141300000
_diffrn_oxdiff_ac4_digest_frames 
;
01b1b344d8eb41fa769700420691ce998506668a610
;
_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         0.666
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.988
_reflns_number_gt                2476
_reflns_number_total             2533
_reflns_odcompleteness_completeness 99.93
_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 1.171.40.23a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.23a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.23a (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.235
_refine_diff_density_min         -0.184
_refine_diff_density_rms         0.037
_refine_ls_abs_structure_details 
;
 Flack x determined using 984 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.008(6)
_refine_ls_extinction_coef       0.0005(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2016/4 (Sheldrick 2016)'
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     166
_refine_ls_number_reflns         2533
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0244
_refine_ls_R_factor_gt           0.0240
_refine_ls_restrained_S_all      1.047
_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)+(0.0370P)²+0.3325P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0658
_refine_ls_wR_factor_ref         0.0660
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C14(H14), C12(H12), C11(H11), C7(H7), C4(H4), C6(H6), C5(H5)
2.b Idealised tetrahedral OH refined as rotating group:
 O16(H16), O18(H18)
;
_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
P15 P 0.77328(11) 0.30109(6) 0.07869(2) 0.03291(15) Uani 1 1 d . . . . .
S9 S 0.43582(13) 0.31682(9) 0.29596(2) 0.0516(2) Uani 1 1 d . . . . .
S2 S 0.8637(2) 0.08743(6) 0.32346(3) 0.0526(2) Uani 1 1 d . . . . .
O16 O 0.5591(4) 0.41033(17) 0.07530(8) 0.0410(4) Uani 1 1 d . . . . .
H16 H 0.401947 0.381124 0.072323 0.062 Uiso 1 1 calc GR . . . .
O17 O 1.0422(4) 0.3425(2) 0.05369(7) 0.0440(4) Uani 1 1 d . . . . .
O18 O 0.6494(4) 0.18196(18) 0.05062(7) 0.0472(4) Uani 1 1 d . . . . .
H18 H 0.642205 0.192635 0.016839 0.071 Uiso 1 1 calc GR . . . .
C14 C 0.6514(5) 0.3050(2) 0.19163(9) 0.0364(5) Uani 1 1 d . . . . .
H14 H 0.534248 0.372556 0.184121 0.044 Uiso 1 1 calc R . . . .
C10 C 0.6676(5) 0.2565(2) 0.24538(10) 0.0369(5) Uani 1 1 d . . . . .
C13 C 0.8094(5) 0.2528(2) 0.14937(9) 0.0345(5) Uani 1 1 d . . . . .
C3 C 0.8271(6) 0.2193(2) 0.36798(9) 0.0413(6) Uani 1 1 d . . . . .
C1 C 0.8492(6) 0.1582(2) 0.25698(9) 0.0385(5) Uani 1 1 d . . . . .
C12 C 0.9963(6) 0.1563(3) 0.16143(10) 0.0445(6) Uani 1 1 d . . . . .
H12 H 1.106899 0.122890 0.133328 0.053 Uiso 1 1 calc R . . . .
C8 C 0.6421(5) 0.3153(3) 0.35675(9) 0.0402(5) Uani 1 1 d . . . . .
C11 C 1.0176(7) 0.1101(3) 0.21524(11) 0.0472(6) Uani 1 1 d . . . . .
H11 H 1.145018 0.046849 0.223346 0.057 Uiso 1 1 calc R . . . .
C7 C 0.6068(6) 0.4126(3) 0.39481(10) 0.0468(6) Uani 1 1 d . . . . .
H7 H 0.481838 0.477302 0.387379 0.056 Uiso 1 1 calc R . . . .
C4 C 0.9878(7) 0.2227(3) 0.41651(11) 0.0509(7) Uani 1 1 d . . . . .
H4 H 1.118853 0.160193 0.423420 0.061 Uiso 1 1 calc R . . . .
C6 C 0.7584(7) 0.4129(3) 0.44375(11) 0.0522(7) Uani 1 1 d . . . . .
H6 H 0.730353 0.476502 0.469804 0.063 Uiso 1 1 calc R . . . .
C5 C 0.9501(7) 0.3199(3) 0.45411(11) 0.0572(8) Uani 1 1 d . . . . .
H5 H 1.055130 0.322228 0.486604 0.069 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
P15 O16 1.5536(18) . ?
P15 O17 1.4923(18) . ?
P15 O18 1.5522(18) . ?
P15 C13 1.782(2) . ?
S9 C10 1.769(2) . ?
S9 C8 1.765(2) . ?
S2 C3 1.770(3) . ?
S2 C1 1.766(2) . ?
O16 H16 0.8200 . ?
O18 H18 0.8200 . ?
C14 H14 0.9300 . ?
C14 C10 1.392(3) . ?
C14 C13 1.383(3) . ?
C10 C1 1.389(4) . ?
C13 C12 1.393(3) . ?
C3 C8 1.380(4) . ?
C3 C4 1.399(4) . ?
C1 C11 1.386(4) . ?
C12 H12 0.9300 . ?
C12 C11 1.386(4) . ?
C8 C7 1.390(4) . ?
C11 H11 0.9300 . ?
C7 H7 0.9300 . ?
C7 C6 1.383(4) . ?
C4 H4 0.9300 . ?
C4 C5 1.383(4) . ?
C6 H6 0.9300 . ?
C6 C5 1.374(5) . ?
C5 H5 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
O16 P15 C13 109.22(11) . . ?
O17 P15 O16 109.49(11) . . ?
O17 P15 O18 113.46(11) . . ?
O17 P15 C13 112.57(11) . . ?
O18 P15 O16 109.34(11) . . ?
O18 P15 C13 102.53(10) . . ?
C8 S9 C10 102.15(12) . . ?
C1 S2 C3 101.86(11) . . ?
P15 O16 H16 109.5 . . ?
P15 O18 H18 109.5 . . ?
C10 C14 H14 119.9 . . ?
C13 C14 H14 119.9 . . ?
C13 C14 C10 120.1(2) . . ?
C14 C10 S9 117.89(19) . . ?
C1 C10 S9 122.05(18) . . ?
C1 C10 C14 119.9(2) . . ?
C14 C13 P15 122.04(19) . . ?
C14 C13 C12 119.7(2) . . ?
C12 C13 P15 118.18(18) . . ?
C8 C3 S2 122.03(19) . . ?
C8 C3 C4 120.0(2) . . ?
C4 C3 S2 118.0(2) . . ?
C10 C1 S2 121.73(18) . . ?
C11 C1 S2 118.28(19) . . ?
C11 C1 C10 119.9(2) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 C13 120.1(2) . . ?
C11 C12 H12 119.9 . . ?
C3 C8 S9 122.08(19) . . ?
C3 C8 C7 120.0(2) . . ?
C7 C8 S9 117.9(2) . . ?
C1 C11 H11 120.0 . . ?
C12 C11 C1 120.0(2) . . ?
C12 C11 H11 120.0 . . ?
C8 C7 H7 120.1 . . ?
C6 C7 C8 119.8(3) . . ?
C6 C7 H7 120.1 . . ?
C3 C4 H4 120.3 . . ?
C5 C4 C3 119.4(3) . . ?
C5 C4 H4 120.3 . . ?
C7 C6 H6 119.8 . . ?
C5 C6 C7 120.4(3) . . ?
C5 C6 H6 119.8 . . ?
C4 C5 H5 119.8 . . ?
C6 C5 C4 120.4(3) . . ?
C6 C5 H5 119.8 . . ?

_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 1.313
_oxdiff_exptl_absorpt_empirical_full_min 0.833
####################################################################### 
# 
# 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_gl313_1
_database_code_depnum_ccdc_archive 'CCDC 2296521'
loop_
_audit_author_name
_audit_author_address
'Geoffrey Letheux Olivier Perez'
;CRISMAT
France
;
_audit_update_record             
;
2023-09-21 deposited with the CCDC.	2023-11-15 downloaded from the CCDC.
;
_audit_creation_date             2021-11-10
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H9 O4 P S2 Zn'
_chemical_formula_sum            'C12 H9 O4 P S2 Zn'
_chemical_formula_weight         377.65
_chemical_melting_point          ?
_chemical_oxdiff_formula         'S P O3 C12 H7'
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'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Zn Zn -1.5491 0.6778 '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                   22.0947(5)
_cell_length_b                   7.8428(2)
_cell_length_c                   7.8758(2)
_cell_angle_alpha                90
_cell_angle_beta                 95.283(2)
_cell_angle_gamma                90
_cell_volume                     1358.96(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4892
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      75.2570
_cell_measurement_theta_min      4.0400
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    6.596
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.76561
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.23a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light white'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    white
_exptl_crystal_density_diffrn    1.846
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       needle
_exptl_crystal_F_000             760
_exptl_crystal_size_max          0.073
_exptl_crystal_size_mid          0.048
_exptl_crystal_size_min          0.018
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0797
_diffrn_reflns_av_unetI/netI     0.0368
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            27137
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.944
_diffrn_reflns_theta_min         4.019
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'Eiger 1M'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -17.00  68.00   0.50    8.24    --   -0.75  53.00 -24.00  170
  2  ω     28.00 113.00   0.50    8.24    --   43.75  53.00 -24.00  170
  3  ω     94.00 171.00   0.50    8.24    --  110.00  53.00 -24.00  154
  4  ω    133.00 171.00   0.50    8.24    --  110.00  61.00   0.00   76
  5  ω    146.00 171.00   0.50    8.24    --  110.00  75.00  73.61   50
  6  ω    123.00 148.00   0.50    8.24    --  110.00 125.00  60.00   50
  7  ω    117.00 171.00   0.50    8.24    --  110.00  69.00  94.11  108
  8  ω    125.00 154.00   0.50    8.24    --  110.00  45.00 120.00   58
  9  ω    116.00 141.00   0.50    8.24    --  110.00  15.00  90.00   50
 10  ω    103.00 129.00   0.50    8.24    --  110.00  61.00  30.00   52
 11  ω    108.00 171.00   0.50    8.24    --  110.00  30.00 -30.00  126
 12  ω    125.00 152.00   0.50    8.24    --  110.00  64.00-130.26   54
 13  ω    137.00 171.00   0.50    8.24    --  110.00  61.00-150.00   68
 14  ω    121.00 147.00   0.50    8.24    --  110.00 125.00-150.00   52
 15  ω    118.00 155.00   0.50    8.24    --  110.00 125.00-120.00   74
 16  ω    117.00 171.00   0.50    8.24    --  110.00 125.00 -60.00  108
 17  ω     90.00 171.00   0.50    8.24    --  110.00  30.00  30.00  162
 18  ω     92.00 171.00   0.50    8.24    --  110.00  32.00 -55.36  158
 19  ω     89.00 171.00   0.50    8.24    --  110.00  61.00 -90.00  164
 20  ω     89.00 171.00   0.50    8.24    --  110.00  61.00-120.00  164
 21  ω     91.00 117.00   0.50    8.24    --  110.00 -45.00 -30.00   52
 22  ω     77.00 127.00   0.50    8.24    --  110.00  15.00  60.00  100
 23  ω     97.00 123.00   0.50    8.24    --  110.00  45.00  30.00   52
 24  ω     99.00 125.00   0.50    8.24    --  110.00  45.00  90.00   52
 25  ω     81.00 171.00   0.50    8.24    --  110.00  77.00  60.00  180
 26  ω     89.00 171.00   0.50    8.24    --  110.00  61.00  60.00  164
 27  ω     91.00 134.00   0.50    8.24    --  110.00  59.00  95.51   86
 28  ω     81.00 171.00   0.50    8.24    --  110.00  77.00  30.00  180
 29  ω     92.00 117.00   0.50    8.24    --  110.00  61.00 -60.00   50
 30  ω     83.00 171.00   0.50    8.24    --  110.00  73.00  21.93  176
 31  ω     89.00 152.00   0.50    8.24    --  110.00  61.00 120.00  126
 32  ω     82.00 116.00   0.50    8.24    --  110.00  75.00  73.61   68
 33  ω     85.00 114.00   0.50    8.24    --  110.00  69.00  94.11   58
 34  ω     83.00 115.00   0.50    8.24    --  110.00  77.00 109.76   64
 35  ω     86.00 112.00   0.50    8.24    --  110.00  77.00 120.00   52
 36  ω     81.00 171.00   0.50    8.24    --  110.00  77.00  90.00  180
 37  ω     76.00 171.00   0.50    8.24    --  110.00  15.00 120.00  190
 38  ω     80.00 171.00   0.50    8.24    --  110.00  80.00  34.62  182
 39  ω     67.00 109.00   0.50    8.24    --  110.00   0.00 120.00   84
 40  ω     44.00 107.00   0.50    8.24    --  110.00 -61.00 150.00  126
 41  ω     38.00  83.00   0.50    8.24    --  110.00 -94.00 120.00   90
 42  ω     34.00 129.00   0.50    8.24    --  110.00 -30.00  60.00  190
 43  ω     80.00 105.00   0.50    8.24    --  110.00-125.00 -60.00   50
 44  ω     61.00  87.00   0.50    8.24    --  110.00-125.00  30.00   52
 45  ω     43.00  90.00   0.50    8.24    --  110.00-135.00 -33.04   94
 46  ω     41.00 126.00   0.50    8.24    --  110.00 -53.00-168.00  170
 47  ω     46.00  75.00   0.50    8.24    --  110.00 -45.00 -30.00   58
 48  ω     38.00 123.00   0.50    8.24    --  110.00 -45.00-150.00  170
 49  ω     39.00 106.00   0.50    8.24    --  110.00-125.00-180.00  134
 50  ω     -2.00  83.00   0.50    8.24    --   43.75 -99.00 -30.00  170
 51  ω     -2.00  83.00   0.50    8.24    --   43.75 -99.00-180.00  170
 52  ω    -25.00  60.00   0.50    8.24    --   43.75 -53.00-168.00  170
 53  ω     26.00 111.00   0.50    8.24    --   43.75  57.00   0.00  170
 54  ω     26.00 111.00   0.50    8.24    --   43.75  57.00  60.00  170
 55  ω     26.00 111.00   0.50    8.24    --   43.75  57.00 120.00  170
 56  ω     -2.00  83.00   0.50    8.24    --   43.75 -99.00  30.00  170
 57  ω    -70.00  15.00   0.50    8.24    --   -0.75 -53.00-168.00  170
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, Eiger 1M'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.1719963000
_diffrn_orient_matrix_UB_12      -0.0155587000
_diffrn_orient_matrix_UB_13      -0.0275774000
_diffrn_orient_matrix_UB_21      0.0636526000
_diffrn_orient_matrix_UB_22      -0.1246543000
_diffrn_orient_matrix_UB_23      0.0510166000
_diffrn_orient_matrix_UB_31      -0.0703985000
_diffrn_orient_matrix_UB_32      -0.1509699000
_diffrn_orient_matrix_UB_33      -0.0392624000
_diffrn_oxdiff_ac4_digest_frames 
;
0102a4255d4e1154baa232b77341b5b7a6000259dfa
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\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                2449
_reflns_number_total             2810
_reflns_odcompleteness_completeness 99.94
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     50.38
_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 1.171.40.23a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.23a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.23a (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.588
_refine_diff_density_min         -0.558
_refine_diff_density_rms         0.079
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.006
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     186
_refine_ls_number_reflns         2810
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0451
_refine_ls_R_factor_gt           0.0372
_refine_ls_restrained_S_all      1.006
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1223
_refine_ls_wR_factor_ref         0.1283
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Free rotating group:
 O4(H4A,H4B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C5(H5), C6(H6), C8(H8), C11(H11), C10(H10), C9(H9)
;
_atom_sites_solution_hydrogens   mixed
_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
Zn1 Zn 0.95746(2) 0.55071(5) 0.23030(5) 0.02574(16) Uani 1 1 d . . . . .
P1 P 0.91808(3) 0.57134(9) 0.59808(9) 0.0213(2) Uani 1 1 d . . . . .
S2 S 0.72857(4) 0.28587(13) 0.90139(12) 0.0408(2) Uani 1 1 d . . . . .
S1 S 0.64228(4) 0.59978(13) 0.76631(14) 0.0432(3) Uani 1 1 d . . . . .
O1 O 0.91748(11) 0.4877(3) 0.4248(3) 0.0356(5) Uani 1 1 d . . . . .
O3 O 0.94363(11) 0.7480(3) 0.5936(3) 0.0352(5) Uani 1 1 d . . . . .
O2 O 0.95291(9) 0.4562(3) 0.7302(3) 0.0337(6) Uani 1 1 d . . . . .
C2 C 0.81597(14) 0.4446(4) 0.7368(4) 0.0267(6) Uani 1 1 d . . . . .
H2 H 0.839676 0.349613 0.767544 0.032 Uiso 1 1 calc R U . . .
C1 C 0.84093(13) 0.5793(4) 0.6530(4) 0.0248(6) Uani 1 1 d . . . . .
C3 C 0.75573(14) 0.4503(4) 0.7756(4) 0.0278(6) Uani 1 1 d . . . . .
C4 C 0.71919(14) 0.5881(5) 0.7201(4) 0.0320(7) Uani 1 1 d . . . . .
C5 C 0.74368(15) 0.7220(4) 0.6321(5) 0.0367(8) Uani 1 1 d . . . . .
H5 H 0.719288 0.813516 0.594112 0.044 Uiso 1 1 calc R U . . .
C6 C 0.80446(15) 0.7185(4) 0.6013(5) 0.0347(7) Uani 1 1 d . . . . .
H6 H 0.821039 0.809653 0.545874 0.042 Uiso 1 1 calc R U . . .
C12 C 0.61861(15) 0.3868(5) 0.7389(5) 0.0375(8) Uani 1 1 d . . . . .
C7 C 0.65531(15) 0.2506(5) 0.7974(5) 0.0356(7) Uani 1 1 d . . . . .
C8 C 0.63404(19) 0.0835(6) 0.7786(6) 0.0482(10) Uani 1 1 d . . . . .
H8 H 0.658848 -0.007355 0.815986 0.058 Uiso 1 1 calc R U . . .
C11 C 0.56085(17) 0.3536(6) 0.6589(5) 0.0480(9) Uani 1 1 d . . . . .
H11 H 0.536631 0.442594 0.613878 0.058 Uiso 1 1 calc R U . . .
C10 C 0.53961(19) 0.1862(7) 0.6469(6) 0.0579(12) Uani 1 1 d . . . . .
H10 H 0.500268 0.164316 0.599419 0.069 Uiso 1 1 calc R U . . .
C9 C 0.5763(2) 0.0540(6) 0.7045(7) 0.0565(12) Uani 1 1 d . . . . .
H9 H 0.561911 -0.057326 0.693415 0.068 Uiso 1 1 calc R U . . .
O4 O 0.92910(11) 0.3794(3) 0.0556(3) 0.0343(5) Uani 1 1 d G . . A -1
H4A H 0.934105 0.406793 -0.060891 0.08(2) Uiso 1 1 d G . . A -1
H4B H 0.938101 0.260084 0.064833 0.11(2) Uiso 1 1 d G . . A -1


_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
Zn1 O1 1.903(2) . ?
Zn1 O3 1.919(2) 4_575 ?
Zn1 O2 1.977(2) 3_766 ?
Zn1 O4 1.983(2) . ?
P1 O1 1.513(2) . ?
P1 O3 1.498(2) . ?
P1 O2 1.530(2) . ?
P1 C1 1.798(3) . ?
S2 C3 1.765(3) . ?
S2 C7 1.767(4) . ?
S1 C4 1.773(3) . ?
S1 C12 1.758(4) . ?
C2 H2 0.9300 . ?
C2 C1 1.386(4) . ?
C2 C3 1.393(4) . ?
C1 C6 1.396(4) . ?
C3 C4 1.395(5) . ?
C4 C5 1.395(5) . ?
C5 H5 0.9300 . ?
C5 C6 1.387(5) . ?
C6 H6 0.9300 . ?
C12 C7 1.393(5) . ?
C12 C11 1.395(5) . ?
C7 C8 1.396(5) . ?
C8 H8 0.9300 . ?
C8 C9 1.373(6) . ?
C11 H11 0.9300 . ?
C11 C10 1.395(7) . ?
C10 H10 0.9300 . ?
C10 C9 1.367(7) . ?
C9 H9 0.9300 . ?
O4 H4A 0.9586 . ?
O4 H4B 0.9583 . ?

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 Zn1 O3 127.13(11) . 4_575 ?
O1 Zn1 O2 113.50(10) . 3_766 ?
O1 Zn1 O4 104.02(10) . . ?
O3 Zn1 O2 102.48(10) 4_575 3_766 ?
O3 Zn1 O4 98.28(11) 4_575 . ?
O2 Zn1 O4 109.80(11) 3_766 . ?
O1 P1 O2 108.63(15) . . ?
O1 P1 C1 107.57(14) . . ?
O3 P1 O1 110.59(14) . . ?
O3 P1 O2 113.27(14) . . ?
O3 P1 C1 109.97(14) . . ?
O2 P1 C1 106.59(13) . . ?
C3 S2 C7 101.44(16) . . ?
C12 S1 C4 101.86(17) . . ?
P1 O1 Zn1 130.34(15) . . ?
P1 O3 Zn1 142.02(17) . 4_576 ?
P1 O2 Zn1 123.84(13) . 3_766 ?
C1 C2 H2 119.7 . . ?
C1 C2 C3 120.7(3) . . ?
C3 C2 H2 119.7 . . ?
C2 C1 P1 121.0(2) . . ?
C2 C1 C6 119.4(3) . . ?
C6 C1 P1 119.5(2) . . ?
C2 C3 S2 118.7(2) . . ?
C2 C3 C4 119.5(3) . . ?
C4 C3 S2 121.7(2) . . ?
C3 C4 S1 120.9(3) . . ?
C3 C4 C5 120.0(3) . . ?
C5 C4 S1 119.1(3) . . ?
C4 C5 H5 120.1 . . ?
C6 C5 C4 119.9(3) . . ?
C6 C5 H5 120.1 . . ?
C1 C6 H6 119.8 . . ?
C5 C6 C1 120.5(3) . . ?
C5 C6 H6 119.8 . . ?
C7 C12 S1 122.0(3) . . ?
C7 C12 C11 119.1(4) . . ?
C11 C12 S1 118.9(3) . . ?
C12 C7 S2 120.9(3) . . ?
C12 C7 C8 120.3(3) . . ?
C8 C7 S2 118.8(3) . . ?
C7 C8 H8 120.2 . . ?
C9 C8 C7 119.6(4) . . ?
C9 C8 H8 120.2 . . ?
C12 C11 H11 120.2 . . ?
C10 C11 C12 119.7(4) . . ?
C10 C11 H11 120.2 . . ?
C11 C10 H10 119.8 . . ?
C9 C10 C11 120.4(4) . . ?
C9 C10 H10 119.8 . . ?
C8 C9 H9 119.6 . . ?
C10 C9 C8 120.8(4) . . ?
C10 C9 H9 119.6 . . ?
Zn1 O4 H4A 117.1 . . ?
Zn1 O4 H4B 124.0 . . ?
H4A O4 H4B 104.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
P1 C1 C6 C5 175.6(3) . . . . ?
S2 C3 C4 S1 -2.7(4) . . . . ?
S2 C3 C4 C5 175.0(3) . . . . ?
S2 C7 C8 C9 177.3(3) . . . . ?
S1 C4 C5 C6 177.2(3) . . . . ?
S1 C12 C7 S2 -0.6(4) . . . . ?
S1 C12 C7 C8 177.7(3) . . . . ?
S1 C12 C11 C10 -175.4(3) . . . . ?
O1 P1 O3 Zn1 174.2(2) . . . 4_576 ?
O1 P1 O2 Zn1 81.1(2) . . . 3_766 ?
O1 P1 C1 C2 88.1(3) . . . . ?
O1 P1 C1 C6 -88.0(3) . . . . ?
O3 P1 O1 Zn1 14.5(3) . . . . ?
O3 P1 O2 Zn1 -42.2(2) . . . 3_766 ?
O3 P1 C1 C2 -151.4(3) . . . . ?
O3 P1 C1 C6 32.5(3) . . . . ?
O2 P1 O1 Zn1 -110.4(2) . . . . ?
O2 P1 O3 Zn1 -63.6(3) . . . 4_576 ?
O2 P1 C1 C2 -28.2(3) . . . . ?
O2 P1 C1 C6 155.6(3) . . . . ?
C2 C1 C6 C5 -0.6(5) . . . . ?
C2 C3 C4 S1 179.9(3) . . . . ?
C2 C3 C4 C5 -2.4(5) . . . . ?
C1 P1 O1 Zn1 134.6(2) . . . . ?
C1 P1 O3 Zn1 55.6(3) . . . 4_576 ?
C1 P1 O2 Zn1 -163.27(17) . . . 3_766 ?
C1 C2 C3 S2 -173.6(2) . . . . ?
C1 C2 C3 C4 4.0(5) . . . . ?
C3 S2 C7 C12 -41.5(3) . . . . ?
C3 S2 C7 C8 140.2(3) . . . . ?
C3 C2 C1 P1 -178.6(2) . . . . ?
C3 C2 C1 C6 -2.5(5) . . . . ?
C3 C4 C5 C6 -0.6(6) . . . . ?
C4 S1 C12 C7 41.6(3) . . . . ?
C4 S1 C12 C11 -139.6(3) . . . . ?
C4 C5 C6 C1 2.1(6) . . . . ?
C12 S1 C4 C3 -39.7(3) . . . . ?
C12 S1 C4 C5 142.6(3) . . . . ?
C12 C7 C8 C9 -1.1(6) . . . . ?
C12 C11 C10 C9 -3.6(7) . . . . ?
C7 S2 C3 C2 -139.2(3) . . . . ?
C7 S2 C3 C4 43.3(3) . . . . ?
C7 C12 C11 C10 3.4(6) . . . . ?
C7 C8 C9 C10 0.9(7) . . . . ?
C11 C12 C7 S2 -179.4(3) . . . . ?
C11 C12 C7 C8 -1.0(5) . . . . ?
C11 C10 C9 C8 1.5(7) . . . . ?

_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 1.445
_oxdiff_exptl_absorpt_empirical_full_min 0.742
####################################################################### 
# 
# 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_gl656_2
_database_code_depnum_ccdc_archive 'CCDC 2296520'
loop_
_audit_author_name
_audit_author_address
'Geoffrey Letheux Olivier Perez'
;CRISMAT
France
;
_audit_update_record             
;
2023-09-21 deposited with the CCDC.	2023-11-15 downloaded from the CCDC.
;
_audit_creation_date             2021-11-10
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H10 Co0.5 O4 P S2'
_chemical_formula_sum            'C12 H10 Co0.50 O4 P S2'
_chemical_formula_weight         342.75
_chemical_melting_point          ?
_chemical_oxdiff_formula         'Co P S2 C12 O3 H7'
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'
Co Co -2.3653 3.6143 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   22.1542(2)
_cell_length_b                   7.93590(10)
_cell_length_c                   15.1100(2)
_cell_angle_alpha                90
_cell_angle_beta                 93.8460(10)
_cell_angle_gamma                90
_cell_volume                     2650.56(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    13171
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      75.6090
_cell_measurement_theta_min      3.9900
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    9.604
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.45476
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.23a (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            pink
_exptl_crystal_density_diffrn    1.718
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       colorless
_exptl_crystal_F_000             1396
_exptl_crystal_size_max          0.175
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.024
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0383
_diffrn_reflns_av_unetI/netI     0.0268
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            28423
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.893
_diffrn_reflns_theta_min         4.000
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            'Eiger 1M'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     31.00  57.00   0.50    0.50    --   43.75  57.00 -30.00   52
  2  ω     21.00 108.00   0.50    0.50    --   43.75  77.00-120.00  174
  3  ω    137.00 162.00   0.50    2.00    --  110.00 108.00-112.00   50
  4  ω    121.00 146.00   0.50    2.00    --  110.00 125.00-180.00   50
  5  ω     90.00 158.00   0.50    2.00    --  110.00  61.00 -90.00  136
  6  ω    128.00 153.00   0.50    2.00    --  110.00  45.00 -90.00   50
  7  ω    126.00 151.00   0.50    2.00    --  110.00  15.00 -90.00   50
  8  ω     98.00 148.00   0.50    2.00    --  110.00  61.00 -60.00  100
  9  ω    123.00 149.00   0.50    2.00    --  110.00  45.00  30.00   52
 10  ω    116.00 164.00   0.50    2.00    --  110.00  30.00  90.00   96
 11  ω     98.00 138.00   0.50    2.00    --  110.00  45.00 -30.00   80
 12  ω     83.00 117.00   0.50    2.00    --  110.00  15.00 -90.00   68
 13  ω    100.00 126.00   0.50    2.00    --  110.00  30.00-150.00   52
 14  ω     60.00 123.00   0.50    2.00    --  110.00 -45.00 -60.00  126
 15  ω    101.00 137.00   0.50    2.00    --  110.00 -77.00 -90.00   72
 16  ω    106.00 132.00   0.50    2.00    --  110.00 -88.00 -17.29   52
 17  ω     79.00 105.00   0.50    2.00    --  110.00-125.00 -30.00   52
 18  ω     87.00 113.00   0.50    2.00    --  110.00 -61.00 -90.00   52
 19  ω     75.00 101.00   0.50    2.00    --  110.00 -77.00-150.00   52
 20  ω     58.00 112.00   0.50    2.00    --  110.00-125.00-150.00  108
 21  ω     63.00  99.00   0.50    2.00    --  110.00 -94.00-120.00   72
 22  ω     45.00  71.00   0.50    2.00    --  110.00 -61.00 -90.00   52
 23  ω     60.00 105.00   0.50    2.00    --  110.00 -94.00 -30.00   90
 24  ω     86.00 111.00   0.50    2.00    --  110.00 -77.00  60.00   50
 25  ω     63.00 103.00   0.50    2.00    --  110.00-108.00 151.00   80
 26  ω     92.00 117.00   0.50    2.00    --  110.00 -77.00 150.00   50
 27  ω     88.00 114.00   0.50    2.00    --  110.00 -45.00 150.00   52
 28  ω     60.00  86.00   0.50    2.00    --  110.00-125.00 150.00   52
 29  ω     68.00 106.00   0.50    2.00    --  110.00 -94.00 150.00   76
 30  ω     51.00  77.00   0.50    2.00    --  110.00 -77.00 150.00   52
 31  ω     40.00  65.00   0.50    2.00    --  110.00 -45.00 150.00   50
 32  ω     42.00 112.00   0.50    2.00    --  110.00-125.00 120.00  140
 33  ω     48.00 126.00   0.50    2.00    --  110.00 -30.00  30.00  156
 34  ω     81.00 138.00   0.50    2.00    --  110.00  77.00  90.00  114
 35  ω     88.00 167.00   0.50    2.00    --  110.00  77.00  30.00  158
 36  ω     52.00  92.00   0.50    2.00    --  110.00 -77.00 -90.00   80
 37  ω     41.00  79.00   0.50    2.00    --  110.00 -88.00 -17.29   76
 38  ω     51.00  76.00   0.50    2.00    --  110.00 -94.00  30.00   50
 39  ω     22.00  81.00   0.50    0.50    --   43.75-108.00 151.00  118
 40  ω    -13.00  35.00   0.50    0.50    --   -0.75 -94.00  90.00   96
 41  ω     19.00 106.00   0.50    0.50    --   43.75  19.00 120.00  174
 42  ω     39.00  72.00   0.50    2.00    --  110.00 -94.00-150.00   66
 43  ω    -27.00  44.00   0.50    0.50    --   43.75 -38.00-180.00  142
 44  ω    -45.00 -20.00   0.50    0.50    --   -0.75 108.00-112.00   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, Eiger 1M'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0257374000
_diffrn_orient_matrix_UB_12      0.1781939000
_diffrn_orient_matrix_UB_13      -0.0122985000
_diffrn_orient_matrix_UB_21      -0.0634219000
_diffrn_orient_matrix_UB_22      0.0631737000
_diffrn_orient_matrix_UB_23      -0.0324615000
_diffrn_orient_matrix_UB_31      -0.0131527000
_diffrn_orient_matrix_UB_32      0.0441539000
_diffrn_orient_matrix_UB_33      0.0960944000
_diffrn_oxdiff_ac4_digest_frames 
;
01a4ea9daf1bab761e849d0e86408f2c3b03620da75
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\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                5363
_reflns_number_total             5522
_reflns_odcompleteness_completeness 99.98
_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 1.171.40.23a (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.23a (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.23a (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         1.566
_refine_diff_density_min         -0.657
_refine_diff_density_rms         0.160
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.199
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     363
_refine_ls_number_reflns         5522
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0723
_refine_ls_R_factor_gt           0.0713
_refine_ls_restrained_S_all      1.199
_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)+(0.0236P)²+47.8444P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2195
_refine_ls_wR_factor_ref         0.2198
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2. Others
 Fixed Uiso: H7A(0.001)
3.a Free rotating group:
 O8(H8A,H8B), O7(H7A,H7B)
3.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C14(H14), C6(H6), C18(H18), C5(H5), C17(H17), C11(H11), C8(H8),
 C23(H23), C20(H20), C22(H22), C9(H9), C10(H10), C21(H21)
3.c Idealised tetrahedral OH refined as rotating group:
 O4(H4), O1(H1)
;
_atom_sites_solution_hydrogens   mixed
_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
Co1 Co 0.49614(5) 0.67269(14) 0.64047(7) 0.0151(3) Uani 1 1 d . . . . .
P1 P 0.42043(8) 0.5054(2) 0.79641(11) 0.0149(4) Uani 1 1 d . . . . .
P2 P 0.42075(8) 0.3418(2) 0.54126(11) 0.0163(4) Uani 1 1 d . . . . .
S1 S 0.22600(9) 0.7783(3) 0.60390(14) 0.0327(5) Uani 1 1 d . . . . .
S4 S 0.14435(9) 0.3398(3) 0.39897(16) 0.0365(5) Uani 1 1 d . . . . .
S2 S 0.14632(9) 0.4508(3) 0.64700(16) 0.0366(5) Uani 1 1 d . . . . .
S3 S 0.23200(10) 0.6505(3) 0.35715(15) 0.0383(5) Uani 1 1 d . . . . .
O2 O 0.4495(2) 0.6536(6) 0.7549(3) 0.0204(10) Uani 1 1 d . . . . .
O6 O 0.4510(2) 0.2585(7) 0.4657(3) 0.0215(11) Uani 1 1 d . . . . .
O3 O 0.4485(2) 0.3351(6) 0.7796(3) 0.0201(11) Uani 1 1 d . . . . .
O5 O 0.4412(2) 0.5157(7) 0.5652(4) 0.0251(12) Uani 1 1 d . . . . .
O4 O 0.4286(3) 0.2136(7) 0.6213(3) 0.0236(11) Uani 1 1 d . . . . .
H4 H 0.436948 0.265629 0.667451 0.035 Uiso 1 1 calc R U . . .
O1 O 0.4212(2) 0.5319(7) 0.9004(3) 0.0229(11) Uani 1 1 d . . . . .
H1 H 0.432050 0.444539 0.925679 0.034 Uiso 1 1 calc R U . . .
C13 C 0.3408(3) 0.3469(9) 0.5101(5) 0.0207(15) Uani 1 1 d . . . . .
C2 C 0.3164(3) 0.6247(10) 0.7034(5) 0.0215(15) Uani 1 1 d . . . . .
H2 H 0.339301 0.718771 0.690707 0.026 Uiso 1 1 calc R U . . .
C3 C 0.2561(3) 0.6139(10) 0.6714(5) 0.0240(16) Uani 1 1 d . . . . .
C1 C 0.3423(3) 0.4937(9) 0.7545(5) 0.0197(14) Uani 1 1 d . . . . .
C15 C 0.2572(3) 0.4833(11) 0.4273(5) 0.0251(16) Uani 1 1 d . . . . .
C14 C 0.3168(3) 0.4838(10) 0.4622(5) 0.0259(16) Uani 1 1 d . . . . .
H14 H 0.341024 0.577203 0.453357 0.031 Uiso 1 1 calc R U . . .
C6 C 0.3078(4) 0.3528(11) 0.7744(6) 0.0291(18) Uani 1 1 d . . . . .
H6 H 0.324923 0.266115 0.809043 0.035 Uiso 1 1 calc R U . . .
C18 C 0.3031(4) 0.2111(11) 0.5274(6) 0.0288(17) Uani 1 1 d . . . . .
H18 H 0.318378 0.119497 0.560126 0.035 Uiso 1 1 calc R U . . .
C7 C 0.1522(4) 0.7978(11) 0.6429(5) 0.0288(18) Uani 1 1 d . . . . .
C16 C 0.2197(4) 0.3474(11) 0.4458(5) 0.0276(17) Uani 1 1 d . . . . .
C5 C 0.2479(4) 0.3432(11) 0.7421(6) 0.0312(19) Uani 1 1 d . . . . .
H5 H 0.224800 0.249340 0.754425 0.037 Uiso 1 1 calc R U . . .
C17 C 0.2428(4) 0.2135(12) 0.4954(6) 0.0346(19) Uani 1 1 d . . . . .
H17 H 0.217686 0.123655 0.507667 0.042 Uiso 1 1 calc R U . . .
C12 C 0.1177(4) 0.6569(12) 0.6593(6) 0.0315(19) Uani 1 1 d . . . . .
C4 C 0.2225(3) 0.4742(11) 0.6911(5) 0.0255(16) Uani 1 1 d . . . . .
C19 C 0.1581(4) 0.6846(12) 0.3902(6) 0.0316(19) Uani 1 1 d . . . . .
C11 C 0.0593(4) 0.6763(14) 0.6846(6) 0.039(2) Uani 1 1 d . . . . .
H11 H 0.036382 0.582236 0.697453 0.047 Uiso 1 1 calc R U . . .
C8 C 0.1283(4) 0.9587(13) 0.6527(6) 0.038(2) Uani 1 1 d . . . . .
H8 H 0.152007 1.053141 0.643582 0.046 Uiso 1 1 calc R U . . .
C23 C 0.0630(4) 0.5838(14) 0.4366(6) 0.040(2) Uani 1 1 d . . . . .
H23 H 0.038196 0.495160 0.451660 0.048 Uiso 1 1 calc R U . . .
C24 C 0.1208(4) 0.5504(12) 0.4097(5) 0.0318(19) Uani 1 1 d . . . . .
C20 C 0.1373(5) 0.8498(14) 0.3980(7) 0.045(2) Uani 1 1 d . . . . .
H20 H 0.162784 0.939704 0.387689 0.054 Uiso 1 1 calc R U . . .
C22 C 0.0424(5) 0.7465(16) 0.4410(7) 0.050(3) Uani 1 1 d . . . . .
H22 H 0.003445 0.767452 0.457566 0.060 Uiso 1 1 calc R U . . .
C9 C 0.0694(5) 0.9778(15) 0.6760(7) 0.049(3) Uani 1 1 d . . . . .
H9 H 0.053036 1.084813 0.681676 0.058 Uiso 1 1 calc R U . . .
C10 C 0.0351(5) 0.8359(16) 0.6908(7) 0.050(3) Uani 1 1 d . . . . .
H10 H -0.004833 0.848403 0.705062 0.060 Uiso 1 1 calc R U . . .
C21 C 0.0796(5) 0.8798(15) 0.4206(7) 0.049(3) Uani 1 1 d . . . . .
H21 H 0.065208 0.989711 0.422469 0.059 Uiso 1 1 calc R U . . .
O8 O 0.5591(3) 0.4742(8) 0.6765(5) 0.0435(17) Uani 1 1 d G . . A -1
H8A H 0.555961 0.358629 0.694067 0.001(16) Uiso 1 1 d G . . A -1
H8B H 0.570956 0.469065 0.616694 0.02(2) Uiso 1 1 d G . . A -1
O7 O 0.4343(3) 0.8658(7) 0.5939(4) 0.0263(12) Uani 1 1 d G . . B -1
H7A H 0.432184 0.982846 0.608946 0.001 Uiso 1 1 d G U . B -1
H7B H 0.440036 0.865091 0.531647 0.15(8) Uiso 1 1 d G . . B -1


_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
Co1 O2 2.079(5) . ?
Co1 O6 2.121(5) 3_666 ?
Co1 O3 2.103(5) 2_656 ?
Co1 O5 2.035(5) . ?
Co1 O8 2.150(6) . ?
Co1 O7 2.142(5) . ?
P1 O2 1.499(5) . ?
P1 O3 1.516(5) . ?
P1 O1 1.584(5) . ?
P1 C1 1.804(7) . ?
P2 O6 1.513(5) . ?
P2 O5 1.489(5) . ?
P2 O4 1.582(5) . ?
P2 C13 1.802(8) . ?
S1 C3 1.760(8) . ?
S1 C7 1.782(9) . ?
S4 C16 1.770(8) . ?
S4 C24 1.762(10) . ?
S2 C12 1.768(9) . ?
S2 C4 1.782(8) . ?
S3 C15 1.766(8) . ?
S3 C19 1.764(9) . ?
O4 H4 0.8200 . ?
O1 H1 0.8200 . ?
C13 C14 1.392(11) . ?
C13 C18 1.398(11) . ?
C2 H2 0.9300 . ?
C2 C3 1.392(10) . ?
C2 C1 1.396(10) . ?
C3 C4 1.379(12) . ?
C1 C6 1.399(11) . ?
C15 C14 1.388(11) . ?
C15 C16 1.401(12) . ?
C14 H14 0.9300 . ?
C6 H6 0.9300 . ?
C6 C5 1.384(11) . ?
C18 H18 0.9300 . ?
C18 C17 1.391(12) . ?
C7 C12 1.386(13) . ?
C7 C8 1.394(13) . ?
C16 C17 1.379(12) . ?
C5 H5 0.9300 . ?
C5 C4 1.391(11) . ?
C17 H17 0.9300 . ?
C12 C11 1.383(12) . ?
C19 C24 1.391(13) . ?
C19 C20 1.398(13) . ?
C11 H11 0.9300 . ?
C11 C10 1.381(15) . ?
C8 H8 0.9300 . ?
C8 C9 1.382(14) . ?
C23 H23 0.9300 . ?
C23 C24 1.396(12) . ?
C23 C22 1.372(16) . ?
C20 H20 0.9300 . ?
C20 C21 1.366(15) . ?
C22 H22 0.9300 . ?
C22 C21 1.388(17) . ?
C9 H9 0.9300 . ?
C9 C10 1.385(17) . ?
C10 H10 0.9300 . ?
C21 H21 0.9300 . ?
O8 H8A 0.9587 . ?
O8 H8B 0.9588 . ?
O7 H7A 0.9584 . ?
O7 H7B 0.9580 . ?

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 Co1 O6 168.2(2) . 3_666 ?
O2 Co1 O3 82.5(2) . 2_656 ?
O2 Co1 O8 94.9(2) . . ?
O2 Co1 O7 89.0(2) . . ?
O6 Co1 O8 89.9(2) 3_666 . ?
O6 Co1 O7 86.6(2) 3_666 . ?
O3 Co1 O6 86.9(2) 2_656 3_666 ?
O3 Co1 O8 87.7(3) 2_656 . ?
O3 Co1 O7 94.9(2) 2_656 . ?
O5 Co1 O2 96.2(2) . . ?
O5 Co1 O6 94.3(2) . 3_666 ?
O5 Co1 O3 178.7(2) . 2_656 ?
O5 Co1 O8 92.7(3) . . ?
O5 Co1 O7 84.8(2) . . ?
O7 Co1 O8 175.5(3) . . ?
O2 P1 O3 115.9(3) . . ?
O2 P1 O1 109.5(3) . . ?
O2 P1 C1 108.8(3) . . ?
O3 P1 O1 107.9(3) . . ?
O3 P1 C1 106.9(3) . . ?
O1 P1 C1 107.5(3) . . ?
O6 P2 O4 105.3(3) . . ?
O6 P2 C13 106.8(3) . . ?
O5 P2 O6 116.5(3) . . ?
O5 P2 O4 113.2(3) . . ?
O5 P2 C13 108.7(3) . . ?
O4 P2 C13 105.7(3) . . ?
C3 S1 C7 101.1(4) . . ?
C24 S4 C16 102.0(4) . . ?
C12 S2 C4 101.6(4) . . ?
C19 S3 C15 102.0(4) . . ?
P1 O2 Co1 131.0(3) . . ?
P2 O6 Co1 138.8(3) . 3_666 ?
P1 O3 Co1 132.8(3) . 2_646 ?
P2 O5 Co1 149.7(4) . . ?
P2 O4 H4 109.5 . . ?
P1 O1 H1 109.5 . . ?
C14 C13 P2 119.2(6) . . ?
C14 C13 C18 119.1(7) . . ?
C18 C13 P2 121.5(6) . . ?
C3 C2 H2 120.1 . . ?
C3 C2 C1 119.7(7) . . ?
C1 C2 H2 120.1 . . ?
C2 C3 S1 118.2(6) . . ?
C4 C3 S1 122.2(6) . . ?
C4 C3 C2 119.6(7) . . ?
C2 C1 P1 120.4(6) . . ?
C2 C1 C6 120.2(7) . . ?
C6 C1 P1 119.4(6) . . ?
C14 C15 S3 118.7(6) . . ?
C14 C15 C16 119.2(7) . . ?
C16 C15 S3 122.0(6) . . ?
C13 C14 H14 119.5 . . ?
C15 C14 C13 121.1(7) . . ?
C15 C14 H14 119.5 . . ?
C1 C6 H6 120.2 . . ?
C5 C6 C1 119.6(7) . . ?
C5 C6 H6 120.2 . . ?
C13 C18 H18 120.1 . . ?
C17 C18 C13 119.8(8) . . ?
C17 C18 H18 120.1 . . ?
C12 C7 S1 121.2(7) . . ?
C12 C7 C8 120.2(8) . . ?
C8 C7 S1 118.5(7) . . ?
C15 C16 S4 120.2(6) . . ?
C17 C16 S4 119.8(7) . . ?
C17 C16 C15 119.9(7) . . ?
C6 C5 H5 120.1 . . ?
C6 C5 C4 119.8(8) . . ?
C4 C5 H5 120.1 . . ?
C18 C17 H17 119.6 . . ?
C16 C17 C18 120.8(8) . . ?
C16 C17 H17 119.6 . . ?
C7 C12 S2 121.5(7) . . ?
C11 C12 S2 118.7(8) . . ?
C11 C12 C7 119.8(9) . . ?
C3 C4 S2 121.0(6) . . ?
C3 C4 C5 121.0(7) . . ?
C5 C4 S2 117.9(6) . . ?
C24 C19 S3 121.2(7) . . ?
C24 C19 C20 119.7(9) . . ?
C20 C19 S3 119.0(8) . . ?
C12 C11 H11 120.2 . . ?
C10 C11 C12 119.7(10) . . ?
C10 C11 H11 120.2 . . ?
C7 C8 H8 120.0 . . ?
C9 C8 C7 119.9(10) . . ?
C9 C8 H8 120.0 . . ?
C24 C23 H23 119.8 . . ?
C22 C23 H23 119.8 . . ?
C22 C23 C24 120.5(10) . . ?
C19 C24 S4 121.6(7) . . ?
C19 C24 C23 119.1(9) . . ?
C23 C24 S4 119.3(8) . . ?
C19 C20 H20 119.9 . . ?
C21 C20 C19 120.3(11) . . ?
C21 C20 H20 119.9 . . ?
C23 C22 H22 119.9 . . ?
C23 C22 C21 120.2(9) . . ?
C21 C22 H22 119.9 . . ?
C8 C9 H9 120.3 . . ?
C8 C9 C10 119.3(10) . . ?
C10 C9 H9 120.3 . . ?
C11 C10 C9 121.0(9) . . ?
C11 C10 H10 119.5 . . ?
C9 C10 H10 119.5 . . ?
C20 C21 C22 120.1(10) . . ?
C20 C21 H21 119.9 . . ?
C22 C21 H21 119.9 . . ?
Co1 O8 H8A 135.5 . . ?
Co1 O8 H8B 90.4 . . ?
H8A O8 H8B 104.5 . . ?
Co1 O7 H7A 131.0 . . ?
Co1 O7 H7B 101.2 . . ?
H7A O7 H7B 104.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
P1 C1 C6 C5 -179.8(7) . . . . ?
P2 C13 C14 C15 171.9(6) . . . . ?
P2 C13 C18 C17 -174.3(7) . . . . ?
S1 C3 C4 S2 1.2(10) . . . . ?
S1 C3 C4 C5 177.7(7) . . . . ?
S1 C7 C12 S2 2.7(10) . . . . ?
S1 C7 C12 C11 -176.3(7) . . . . ?
S1 C7 C8 C9 174.9(7) . . . . ?
S4 C16 C17 C18 175.2(7) . . . . ?
S2 C12 C11 C10 -177.1(8) . . . . ?
S3 C15 C14 C13 -173.2(6) . . . . ?
S3 C15 C16 S4 -0.4(10) . . . . ?
S3 C15 C16 C17 175.0(7) . . . . ?
S3 C19 C24 S4 -2.2(10) . . . . ?
S3 C19 C24 C23 179.2(7) . . . . ?
S3 C19 C20 C21 177.9(7) . . . . ?
O2 P1 O3 Co1 105.3(4) . . . 2_646 ?
O2 P1 C1 C2 -9.0(7) . . . . ?
O2 P1 C1 C6 171.5(6) . . . . ?
O6 P2 O5 Co1 -93.2(7) . . . . ?
O6 P2 C13 C14 -88.7(7) . . . . ?
O6 P2 C13 C18 86.7(7) . . . . ?
O3 P1 O2 Co1 28.9(5) . . . . ?
O3 P1 C1 C2 -134.9(6) . . . . ?
O3 P1 C1 C6 45.7(7) . . . . ?
O5 P2 O6 Co1 -16.7(6) . . . 3_666 ?
O5 P2 C13 C14 37.8(7) . . . . ?
O5 P2 C13 C18 -146.9(6) . . . . ?
O4 P2 O6 Co1 -143.0(4) . . . 3_666 ?
O4 P2 O5 Co1 29.1(8) . . . . ?
O4 P2 C13 C14 159.5(6) . . . . ?
O4 P2 C13 C18 -25.1(7) . . . . ?
O1 P1 O2 Co1 151.2(4) . . . . ?
O1 P1 O3 Co1 -17.8(5) . . . 2_646 ?
O1 P1 C1 C2 109.5(6) . . . . ?
O1 P1 C1 C6 -70.0(7) . . . . ?
C13 P2 O6 Co1 104.9(5) . . . 3_666 ?
C13 P2 O5 Co1 146.2(7) . . . . ?
C13 C18 C17 C16 0.8(14) . . . . ?
C2 C3 C4 S2 -176.9(6) . . . . ?
C2 C3 C4 C5 -0.3(12) . . . . ?
C2 C1 C6 C5 0.8(12) . . . . ?
C3 S1 C7 C12 -43.3(8) . . . . ?
C3 S1 C7 C8 139.7(7) . . . . ?
C3 C2 C1 P1 179.9(6) . . . . ?
C3 C2 C1 C6 -0.6(11) . . . . ?
C1 P1 O2 Co1 -91.5(4) . . . . ?
C1 P1 O3 Co1 -133.2(4) . . . 2_646 ?
C1 C2 C3 S1 -177.7(6) . . . . ?
C1 C2 C3 C4 0.4(11) . . . . ?
C1 C6 C5 C4 -0.7(13) . . . . ?
C15 S3 C19 C24 -39.9(8) . . . . ?
C15 S3 C19 C20 139.1(7) . . . . ?
C15 C16 C17 C18 -0.2(13) . . . . ?
C14 C13 C18 C17 1.0(12) . . . . ?
C14 C15 C16 S4 -177.7(6) . . . . ?
C14 C15 C16 C17 -2.3(12) . . . . ?
C6 C5 C4 S2 177.1(7) . . . . ?
C6 C5 C4 C3 0.5(13) . . . . ?
C18 C13 C14 C15 -3.6(12) . . . . ?
C7 S1 C3 C2 -140.7(6) . . . . ?
C7 S1 C3 C4 41.2(8) . . . . ?
C7 C12 C11 C10 1.9(14) . . . . ?
C7 C8 C9 C10 1.1(15) . . . . ?
C16 S4 C24 C19 43.2(8) . . . . ?
C16 S4 C24 C23 -138.2(7) . . . . ?
C16 C15 C14 C13 4.3(12) . . . . ?
C12 S2 C4 C3 -42.2(7) . . . . ?
C12 S2 C4 C5 141.1(7) . . . . ?
C12 C7 C8 C9 -2.2(13) . . . . ?
C12 C11 C10 C9 -3.0(15) . . . . ?
C4 S2 C12 C7 39.9(8) . . . . ?
C4 S2 C12 C11 -141.2(7) . . . . ?
C19 S3 C15 C14 -141.3(7) . . . . ?
C19 S3 C15 C16 41.3(8) . . . . ?
C19 C20 C21 C22 3.6(15) . . . . ?
C8 C7 C12 S2 179.6(7) . . . . ?
C8 C7 C12 C11 0.7(13) . . . . ?
C8 C9 C10 C11 1.5(16) . . . . ?
C23 C22 C21 C20 -1.3(16) . . . . ?
C24 S4 C16 C15 -41.5(8) . . . . ?
C24 S4 C16 C17 143.1(7) . . . . ?
C24 C19 C20 C21 -3.1(14) . . . . ?
C24 C23 C22 C21 -1.5(15) . . . . ?
C20 C19 C24 S4 178.8(7) . . . . ?
C20 C19 C24 C23 0.2(13) . . . . ?
C22 C23 C24 S4 -176.6(8) . . . . ?
C22 C23 C24 C19 2.1(14) . . . . ?

_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 1.719
_oxdiff_exptl_absorpt_empirical_full_min 0.706
####################################################################### 
# 
# 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_gl419_2
_database_code_depnum_ccdc_archive 'CCDC 2296519'
loop_
_audit_author_name
_audit_author_address
'Geoffrey Letheux Olivier Perez'
;CRISMAT
France
;
_audit_update_record             
;
2023-09-21 deposited with the CCDC.	2023-11-15 downloaded from the CCDC.
;
_audit_creation_date             2023-09-05
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H9 Cu O4 P S2'
_chemical_formula_sum            'C12 H9 Cu O4 P S2'
_chemical_formula_weight         375.82
_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 0.0181 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'
Cu Cu -1.9646 0.5888 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   22.0156(5)
_cell_length_b                   7.6616(2)
_cell_length_c                   7.5811(2)
_cell_angle_alpha                90
_cell_angle_beta                 95.297(2)
_cell_angle_gamma                90
_cell_volume                     1273.28(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5079
_cell_measurement_temperature    290.15(10)
_cell_measurement_theta_max      73.5490
_cell_measurement_theta_min      4.0550
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    6.783
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.57609
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            green
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.961
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       platelets
_exptl_crystal_F_000             756
_exptl_crystal_size_max          0.078
_exptl_crystal_size_mid          0.072
_exptl_crystal_size_min          0.024
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0810
_diffrn_reflns_av_unetI/netI     0.0435
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.991
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            21112
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.991
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.140
_diffrn_reflns_theta_min         4.033
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 13.3333
_diffrn_detector_type            'Eiger 1M'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.991
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -76.00  17.00   0.50    0.20    --   -0.75 -33.00 149.00  186
  2  ω     26.00 119.00   0.50    0.20    --   43.75  33.00 -51.00  186
  3  ω    -31.00  61.00   0.50    0.20    --   43.75 -33.00 149.00  184
  4  ω     92.00 171.00   0.50    0.40    --  110.00  33.00 -51.00  158
  5  ω     35.00 128.00   0.50    0.40    --  110.00 -33.00 149.00  186
  6  ω    -18.00  74.00   0.50    0.20    --   -0.75  33.00 -51.00  184
  7  ω     26.00 111.00   0.50    0.20    --   43.75  57.00-120.00  170
  8  ω     -2.00  83.00   0.50    0.20    --   43.75 -99.00  90.00  170
  9  ω     26.00 111.00   0.50    0.20    --   43.75  57.00   0.00  170
 10  ω    -21.00  72.00   0.50    0.20    --   43.75 -77.00 150.00  186
 11  ω     15.00 108.00   0.50    0.20    --   43.75  77.00  30.00  186
 12  ω     26.00 111.00   0.50    0.20    --   43.75  57.00  30.00  170
 13  ω     85.00 171.00   0.50    0.40    --  110.00  69.00 -28.77  172
 14  ω     89.00 171.00   0.50    0.40    --  110.00  61.00  60.00  164
 15  ω     80.00 171.00   0.50    0.40    --  110.00  80.00   1.85  182
 16  ω     94.00 171.00   0.50    0.40    --  110.00 125.00-180.00  154
 17  ω     76.00 171.00   0.50    0.40    --  110.00  15.00  60.00  190
 18  ω     44.00 130.00   0.50    0.40    --  110.00 -61.00  30.00  172
 19  ω     81.00 171.00   0.50    0.40    --  110.00  77.00  60.00  180
 20  ω     38.00 106.00   0.50    0.40    --  110.00 -94.00-180.00  136
 21  ω     39.00 112.00   0.50    0.40    --  110.00-125.00 120.00  146
 22  ω     89.00 118.00   0.50    0.40    --  110.00  61.00   0.00   58
 23  ω    135.00 169.00   0.50    0.40    --  110.00  61.00   0.00   68
 24  ω     68.00  94.00   0.50    0.40    --  110.00 -61.00-180.00   52
 25  ω     46.00 104.00   0.50    0.40    --  110.00 -45.00 -90.00  116
 26  ω     81.00 107.00   0.50    0.40    --  110.00  77.00   0.00   52
 27  ω     83.00 124.00   0.50    0.40    --  110.00  77.00 -30.00   82
 28  ω    140.00 165.00   0.50    0.40    --  110.00  61.00 120.00   50
 29  ω     69.00 107.00   0.50    0.40    --  110.00-125.00-150.00   76
 30  ω     90.00 117.00   0.50    0.40    --  110.00  61.00  30.00   54
 31  ω     47.00  80.00   0.50    0.40    --  110.00 -45.00  90.00   66
 32  ω     32.00  69.00   0.50    0.40    --  110.00 -15.00  90.00   74
 33  ω     81.00 131.00   0.50    0.40    --  110.00  77.00  90.00  100
 34  ω     98.00 140.00   0.50    0.40    --  110.00 -84.00  35.17   84
 35  ω     59.00  86.00   0.50    0.40    --  110.00 -84.00  35.17   54
 36  ω    116.00 141.00   0.50    0.40    --  110.00 -15.00  90.00   50
 37  ω     81.00 108.00   0.50    0.40    --  110.00  77.00  30.00   54
 38  ω    116.00 171.00   0.50    0.40    --  110.00  77.00 -60.00  110
 39  ω     88.00 113.00   0.50    0.40    --  110.00  67.00  35.46   50
 40  ω    124.00 158.00   0.50    0.40    --  110.00  67.00  35.46   68
 41  ω     42.00  89.00   0.50    0.40    --  110.00-125.00   0.00   94
 42  ω     91.00 132.00   0.50    0.40    --  110.00  30.00  90.00   82
 43  ω     34.00 110.00   0.50    0.40    --  110.00 -30.00  30.00  152
 44  ω     41.00 106.00   0.50    0.40    --  110.00 -94.00  90.00  130
 45  ω    122.00 171.00   0.50    0.40    --  110.00 125.00 -30.00   98
 46  ω     92.00 140.00   0.50    0.40    --  110.00  31.00  43.11   96
 47  ω    116.00 166.00   0.50    0.40    --  110.00  30.00   0.00  100
 48  ω    102.00 128.00   0.50    0.40    --  110.00  61.00 -30.00   52
 49  ω     90.00 115.00   0.50    0.40    --  110.00  61.00 101.76   50
 50  ω     64.00 114.00   0.50    0.40    --  110.00 -61.00-150.00  100
 51  ω     73.00  99.00   0.50    0.40    --  110.00-100.00 132.73   52
 52  ω     98.00 126.00   0.50    0.40    --  110.00  45.00  60.00   56
 53  ω    102.00 128.00   0.50    0.40    --  110.00  45.00  90.00   52
 54  ω     91.00 124.00   0.50    0.40    --  110.00  30.00 120.00   66
 55  ω     90.00 148.00   0.50    0.40    --  110.00  61.00-180.00  116
 56  ω     89.00 135.00   0.50    0.40    --  110.00  61.00 -60.00   92
 57  ω     94.00 120.00   0.50    0.40    --  110.00   0.00 -30.00   52
 58  ω     38.00  64.00   0.50    0.40    --  110.00   0.00 -30.00   52
 59  ω     90.00 116.00   0.50    0.40    --  110.00  61.00  90.00   52
 60  ω     85.00 122.00   0.50    0.40    --  110.00 -45.00  60.00   74
 61  ω     88.00 113.00   0.50    0.40    --  110.00  77.00-120.00   50
 62  ω     69.00  95.00   0.50    0.40    --  110.00 -94.00 -60.00   52
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, Eiger 1M'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2292
_reflns_number_total             2651
_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 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.730
_refine_diff_density_min         -0.916
_refine_diff_density_rms         0.159
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.116
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     186
_refine_ls_number_reflns         2651
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0608
_refine_ls_R_factor_gt           0.0508
_refine_ls_restrained_S_all      1.116
_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)+(0.1022P)²+1.4853P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1436
_refine_ls_wR_factor_ref         0.1659
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
2.a Free rotating group:
 O4(H4A,H4B)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C2(H2), C3(H3), C8(H8), C11(H11), C10(H10), C9(H9)
;
_atom_sites_solution_hydrogens   mixed
_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
Cu1 Cu 0.48468(3) 0.80680(8) 0.55915(7) 0.0262(2) Uani 1 1 d . . . . .
P1 P 0.42842(4) 0.44926(13) 0.64330(11) 0.0197(3) Uani 1 1 d . . . . .
S1 S 0.14761(5) 0.39757(16) 0.77166(16) 0.0357(3) Uani 1 1 d . . . . .
S2 S 0.23069(5) 0.72256(17) 0.92397(14) 0.0347(3) Uani 1 1 d . . . . .
O1 O 0.43631(12) 0.5995(4) 0.5142(3) 0.0238(6) Uani 1 1 d . . . . .
O3 O 0.44727(13) 0.2754(4) 0.5698(4) 0.0263(6) Uani 1 1 d . . . . .
O2 O 0.46256(12) 0.4895(4) 0.8244(3) 0.0238(6) Uani 1 1 d . . . . .
C1 C 0.34856(17) 0.4322(6) 0.6743(5) 0.0236(8) Uani 1 1 d . . . . .
C6 C 0.32190(18) 0.5652(6) 0.7678(5) 0.0262(8) Uani 1 1 d . . . . .
H6 H 0.345343 0.659571 0.811063 0.031 Uiso 1 1 calc R U . . .
C5 C 0.26080(18) 0.5565(5) 0.7960(5) 0.0245(8) Uani 1 1 d . . . . .
C4 C 0.22488(18) 0.4173(6) 0.7295(5) 0.0285(9) Uani 1 1 d . . . . .
C2 C 0.3129(2) 0.2956(6) 0.6073(6) 0.0300(9) Uani 1 1 d . . . . .
H2 H 0.330114 0.208267 0.542790 0.036 Uiso 1 1 calc R U . . .
C3 C 0.2513(2) 0.2868(6) 0.6349(6) 0.0317(9) Uani 1 1 d . . . . .
H3 H 0.227830 0.193221 0.590003 0.038 Uiso 1 1 calc R U . . .
C12 C 0.1578(2) 0.7559(7) 0.8108(6) 0.0318(9) Uani 1 1 d . . . . .
C7 C 0.12206(19) 0.6165(6) 0.7476(5) 0.0310(9) Uani 1 1 d . . . . .
C8 C 0.0635(2) 0.6461(7) 0.6637(6) 0.0372(10) Uani 1 1 d . . . . .
H8 H 0.039866 0.553295 0.617486 0.045 Uiso 1 1 calc R U . . .
C11 C 0.1356(2) 0.9237(7) 0.7882(6) 0.0389(11) Uani 1 1 d . . . . .
H11 H 0.160139 1.017630 0.826081 0.047 Uiso 1 1 calc R U . . .
C10 C 0.0774(2) 0.9541(8) 0.7102(7) 0.0455(12) Uani 1 1 d . . . . .
H10 H 0.062462 1.067367 0.697703 0.055 Uiso 1 1 calc R U . . .
C9 C 0.0415(2) 0.8133(8) 0.6507(7) 0.0461(13) Uani 1 1 d . . . . .
H9 H 0.001804 0.832816 0.601151 0.055 Uiso 1 1 calc R U . . .
O4 O 0.41440(13) 0.9281(4) 0.6584(3) 0.0254(6) Uani 1 1 d G . . A -1
H4A H 0.413606 0.926480 0.784614 0.08(2) Uiso 1 1 d G . . A -1
H4B H 0.418678 1.049016 0.629799 0.014(10) Uiso 1 1 d G . . A -1


_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
Cu1 O1 1.925(3) . ?
Cu1 O3 1.966(3) 3_666 ?
Cu1 O2 1.975(3) 2_656 ?
Cu1 O2 2.384(3) 4_575 ?
Cu1 O4 2.010(3) . ?
P1 O1 1.531(3) . ?
P1 O3 1.517(3) . ?
P1 O2 1.534(3) . ?
P1 C1 1.800(4) . ?
S1 C4 1.766(4) . ?
S1 C7 1.773(5) . ?
S2 C5 1.766(4) . ?
S2 C12 1.766(5) . ?
C1 C6 1.401(6) . ?
C1 C2 1.377(6) . ?
C6 H6 0.9300 . ?
C6 C5 1.383(6) . ?
C5 C4 1.394(6) . ?
C4 C3 1.389(6) . ?
C2 H2 0.9300 . ?
C2 C3 1.392(6) . ?
C3 H3 0.9300 . ?
C12 C7 1.386(7) . ?
C12 C11 1.381(7) . ?
C7 C8 1.403(6) . ?
C8 H8 0.9300 . ?
C8 C9 1.370(8) . ?
C11 H11 0.9300 . ?
C11 C10 1.380(7) . ?
C10 H10 0.9300 . ?
C10 C9 1.388(8) . ?
C9 H9 0.9300 . ?
O4 H4A 0.9583 . ?
O4 H4B 0.9584 . ?

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 Cu1 O3 94.72(12) . 3_666 ?
O1 Cu1 O2 109.67(10) . 4_575 ?
O1 Cu1 O2 163.13(11) . 2_656 ?
O1 Cu1 O4 90.88(12) . . ?
O3 Cu1 O2 90.32(12) 3_666 2_656 ?
O3 Cu1 O2 87.19(11) 3_666 4_575 ?
O3 Cu1 O4 169.25(12) 3_666 . ?
O2 Cu1 O2 86.62(10) 2_656 4_575 ?
O2 Cu1 O4 86.91(12) 2_656 . ?
O4 Cu1 O2 82.28(11) . 4_575 ?
O1 P1 O2 110.23(15) . . ?
O1 P1 C1 107.92(17) . . ?
O3 P1 O1 111.98(16) . . ?
O3 P1 O2 112.17(16) . . ?
O3 P1 C1 106.74(18) . . ?
O2 P1 C1 107.56(16) . . ?
C4 S1 C7 101.7(2) . . ?
C5 S2 C12 102.0(2) . . ?
P1 O1 Cu1 126.92(16) . . ?
P1 O3 Cu1 135.30(18) . 3_666 ?
Cu1 O2 Cu1 93.38(10) 2_646 4_576 ?
P1 O2 Cu1 148.12(16) . 4_576 ?
P1 O2 Cu1 118.50(16) . 2_646 ?
C6 C1 P1 118.2(3) . . ?
C2 C1 P1 122.5(3) . . ?
C2 C1 C6 119.2(4) . . ?
C1 C6 H6 119.9 . . ?
C5 C6 C1 120.1(4) . . ?
C5 C6 H6 119.9 . . ?
C6 C5 S2 118.0(3) . . ?
C6 C5 C4 120.5(4) . . ?
C4 C5 S2 121.4(3) . . ?
C5 C4 S1 121.6(3) . . ?
C3 C4 S1 119.2(3) . . ?
C3 C4 C5 119.1(4) . . ?
C1 C2 H2 119.6 . . ?
C1 C2 C3 120.8(4) . . ?
C3 C2 H2 119.6 . . ?
C4 C3 C2 120.2(4) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C7 C12 S2 121.2(4) . . ?
C11 C12 S2 119.4(4) . . ?
C11 C12 C7 119.4(4) . . ?
C12 C7 S1 121.9(3) . . ?
C12 C7 C8 120.1(5) . . ?
C8 C7 S1 118.0(4) . . ?
C7 C8 H8 120.4 . . ?
C9 C8 C7 119.2(5) . . ?
C9 C8 H8 120.4 . . ?
C12 C11 H11 119.5 . . ?
C10 C11 C12 121.0(5) . . ?
C10 C11 H11 119.5 . . ?
C11 C10 H10 120.4 . . ?
C11 C10 C9 119.1(5) . . ?
C9 C10 H10 120.4 . . ?
C8 C9 C10 121.0(5) . . ?
C8 C9 H9 119.5 . . ?
C10 C9 H9 119.5 . . ?
Cu1 O4 H4A 117.0 . . ?
Cu1 O4 H4B 105.5 . . ?
H4A O4 H4B 104.5 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
P1 C1 C6 C5 -179.4(3) . . . . ?
P1 C1 C2 C3 179.7(3) . . . . ?
S1 C4 C3 C2 -177.0(3) . . . . ?
S1 C7 C8 C9 177.0(4) . . . . ?
S2 C5 C4 S1 -0.8(5) . . . . ?
S2 C5 C4 C3 -177.7(3) . . . . ?
S2 C12 C7 S1 -1.5(5) . . . . ?
S2 C12 C7 C8 177.7(3) . . . . ?
S2 C12 C11 C10 -175.9(4) . . . . ?
O1 P1 O3 Cu1 42.7(3) . . . 3_666 ?
O1 P1 O2 Cu1 -132.50(17) . . . 2_646 ?
O1 P1 O2 Cu1 47.3(3) . . . 4_576 ?
O1 P1 C1 C6 -69.7(3) . . . . ?
O1 P1 C1 C2 109.3(3) . . . . ?
O3 P1 O1 Cu1 -122.6(2) . . . . ?
O3 P1 O2 Cu1 -7.0(2) . . . 2_646 ?
O3 P1 O2 Cu1 172.8(3) . . . 4_576 ?
O3 P1 C1 C6 169.8(3) . . . . ?
O3 P1 C1 C2 -11.3(4) . . . . ?
O2 P1 O1 Cu1 3.0(3) . . . . ?
O2 P1 O3 Cu1 -81.9(3) . . . 3_666 ?
O2 P1 C1 C6 49.3(3) . . . . ?
O2 P1 C1 C2 -131.8(3) . . . . ?
C1 P1 O1 Cu1 120.2(2) . . . . ?
C1 P1 O3 Cu1 160.6(2) . . . 3_666 ?
C1 P1 O2 Cu1 -70.1(3) . . . 4_576 ?
C1 P1 O2 Cu1 110.1(2) . . . 2_646 ?
C1 C6 C5 S2 177.0(3) . . . . ?
C1 C6 C5 C4 -1.0(6) . . . . ?
C1 C2 C3 C4 0.7(7) . . . . ?
C6 C1 C2 C3 -1.4(6) . . . . ?
C6 C5 C4 S1 177.1(3) . . . . ?
C6 C5 C4 C3 0.3(6) . . . . ?
C5 S2 C12 C7 42.0(4) . . . . ?
C5 S2 C12 C11 -139.5(4) . . . . ?
C5 C4 C3 C2 -0.1(7) . . . . ?
C4 S1 C7 C12 -40.1(4) . . . . ?
C4 S1 C7 C8 140.8(3) . . . . ?
C2 C1 C6 C5 1.6(6) . . . . ?
C12 S2 C5 C6 141.2(3) . . . . ?
C12 S2 C5 C4 -40.8(4) . . . . ?
C12 C7 C8 C9 -2.2(7) . . . . ?
C12 C11 C10 C9 -1.3(7) . . . . ?
C7 S1 C4 C5 41.2(4) . . . . ?
C7 S1 C4 C3 -142.0(4) . . . . ?
C7 C12 C11 C10 2.6(7) . . . . ?
C7 C8 C9 C10 3.6(7) . . . . ?
C11 C12 C7 S1 180.0(3) . . . . ?
C11 C12 C7 C8 -0.9(6) . . . . ?
C11 C10 C9 C8 -1.9(8) . . . . ?

_smtbx_masks_void_probe_radius   1.2
_smtbx_masks_void_truncation_radius 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
;
####################################################################### 
# 
# 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_gl1516_2
_database_code_depnum_ccdc_archive 'CCDC 2296522'
loop_
_audit_author_name
_audit_author_address
'Geoffrey Letheux Olivier Perez'
;CRISMAT
France
;
_audit_update_record             
;
2023-09-21 deposited with the CCDC.	2023-11-15 downloaded from the CCDC.
;
_audit_creation_date             2023-09-04
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6226)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C12 H10 Mn0.5 O4 P S2'
_chemical_formula_sum            'C12 H10 Mn0.50 O4 P S2'
_chemical_formula_weight         340.76
_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 0.0181 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'
Mn Mn -0.5299 2.8052 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   22.20022(9)
_cell_length_b                   8.01328(3)
_cell_length_c                   15.22699(7)
_cell_angle_alpha                90
_cell_angle_beta                 93.8226(4)
_cell_angle_gamma                90
_cell_volume                     2702.80(2)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    88009
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      75.6280
_cell_measurement_theta_min      3.9580
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    8.412
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.52812
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.84a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            brown
_exptl_crystal_colour_primary    brown
_exptl_crystal_density_diffrn    1.675
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       platelets
_exptl_crystal_F_000             1388
_exptl_crystal_size_max          0.119
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.023
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0477
_diffrn_reflns_av_unetI/netI     0.0098
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -27
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            186132
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         75.910
_diffrn_reflns_theta_min         3.991
_diffrn_ambient_temperature      293(2)
_diffrn_detector_area_resol_mean 13.3333
_diffrn_detector_type            'Eiger 1M'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -20.00  35.00   0.50    1.50    --   -2.25 -92.00 106.00  110
  2  ω    -40.00  42.00   0.50    1.50    --   -2.25  92.00-141.00  164
  3  ω    -20.00  80.00   0.50    1.50    --   42.54 -92.00 106.00  200
  4  ω     35.00 106.00   0.50    6.00    --  110.00 -92.00 106.00  142
  5  ω    101.00 178.00   0.50    6.00    --  110.00  92.00-141.00  154
  6  ω    -37.00  26.00   0.50    1.50    --   42.54 -19.00-180.00  126
  7  ω     25.00 118.00   0.50    1.50    --   42.54  38.00  60.00  186
  8  ω    -37.00  26.00   0.50    1.50    --   42.54 -19.00-150.00  126
  9  ω    -37.00  26.00   0.50    1.50    --   42.54 -19.00 120.00  126
 10  ω    -37.00  26.00   0.50    1.50    --   42.54 -19.00 -60.00  126
 11  ω      5.00  35.00   0.50    1.50    --   42.54  93.00-156.61   60
 12  ω     87.00 178.00   0.50    6.00    --  110.00  61.00-120.00  182
 13  ω     87.00 178.00   0.50    6.00    --  110.00  61.00 -90.00  182
 14  ω     43.00  71.00   0.50    6.00    --  110.00 -61.00   0.00   56
 15  ω     35.00 107.00   0.50    6.00    --  110.00 -94.00 120.00  144
 16  ω     44.00 105.00   0.50    6.00    --  110.00 -77.00 120.00  122
 17  ω     95.00 178.00   0.50    6.00    --  110.00  45.00-150.00  166
 18  ω     61.00 178.00   0.50    6.00    --  110.00  15.00 120.00  234
 19  ω     44.00 105.00   0.50    6.00    --  110.00 -77.00 150.00  122
 20  ω     40.00 118.00   0.50    6.00    --  110.00-133.00  29.18  156
 21  ω     44.00 105.00   0.50    6.00    --  110.00 -77.00-120.00  122
 22  ω     61.00 178.00   0.50    6.00    --  110.00  15.00 120.00  234
 23  ω     44.00 105.00   0.50    6.00    --  110.00 -77.00-180.00  122
 24  ω     35.00 107.00   0.50    6.00    --  110.00 -94.00-180.00  144
 25  ω     87.00 178.00   0.50    6.00    --  110.00  30.00  30.00  182
 26  ω     87.00 178.00   0.50    6.00    --  110.00  61.00 150.00  182
 27  ω     44.00 105.00   0.50    6.00    --  110.00 -77.00   0.00  122
 28  ω     80.00 176.00   0.50    6.00    --  110.00  75.00  83.97  192
 29  ω     35.00 107.00   0.50    6.00    --  110.00 -94.00 -60.00  144
 30  ω     61.00 178.00   0.50    6.00    --  110.00  15.00-150.00  234
 31  ω     43.00  71.00   0.50    6.00    --  110.00 -61.00-120.00   56
 32  ω     35.00 107.00   0.50    6.00    --  110.00 -94.00-120.00  144
 33  ω     35.00 107.00   0.50    6.00    --  110.00 -94.00  90.00  144
 34  ω     35.00 107.00   0.50    6.00    --  110.00 -94.00 150.00  144
 35  ω     38.00 112.00   0.50    6.00    --  110.00-125.00-180.00  148
 36  ω     38.00 112.00   0.50    6.00    --  110.00-125.00  30.00  148
 37  ω     95.00 178.00   0.50    6.00    --  110.00  45.00-180.00  166
 38  ω     94.00 178.00   0.50    6.00    --  110.00 125.00-120.00  168
 39  ω     94.00 178.00   0.50    6.00    --  110.00 125.00 -60.00  168
 40  ω     40.00 145.00   0.50    6.00    --  110.00 -86.00  40.71  210
 41  ω     43.00  71.00   0.50    6.00    --  110.00 -61.00-150.00   56
 42  ω     12.00 109.00   0.50    1.50    --   42.54  77.00 -60.00  194
 43  ω      5.00  42.00   0.50    1.50    --   42.54  92.00-120.78   74
 44  ω     12.00 109.00   0.50    1.50    --   42.54  77.00-180.00  194
 45  ω    -24.00  73.00   0.50    1.50    --   42.54 -77.00 -30.00  194
 46  ω     23.00 112.00   0.50    1.50    --   42.54  57.00 -90.00  178
 47  ω     -2.00  84.00   0.50    1.50    --   42.54 -99.00-180.00  172
 48  ω    -37.00  26.00   0.50    1.50    --   42.54 -19.00 -30.00  126
 49  ω     12.00 109.00   0.50    1.50    --   42.54  77.00  90.00  194
 50  ω     12.00 109.00   0.50    1.50    --   42.54  77.00  30.00  194
 51  ω     12.00 109.00   0.50    1.50    --   42.54  77.00 120.00  194
 52  ω     87.00 178.00   0.50    6.00    --  110.00  61.00  60.00  182
 53  ω     82.00 176.00   0.50    6.00    --  110.00  72.00  10.50  188
 54  ω     80.00 177.00   0.50    6.00    --  110.00  77.00 -60.00  194
 55  ω     80.00 177.00   0.50    6.00    --  110.00  77.00 -30.00  194
 56  ω     80.00 176.00   0.50    6.00    --  110.00  75.00  -0.40  192
 57  ω     43.00 126.00   0.50    6.00    --  110.00-143.00 114.36  166
 58  ω     87.00 178.00   0.50    6.00    --  110.00  61.00 -60.00  182
 59  ω     95.00 178.00   0.50    6.00    --  110.00  45.00 -30.00  166
 60  ω     80.00 177.00   0.50    6.00    --  110.00  77.00  60.00  194
 61  ω     80.00 177.00   0.50    6.00    --  110.00  77.00 136.97  194
 62  ω     80.00 177.00   0.50    6.00    --  110.00  77.00-120.00  194
 63  ω     80.00 176.00   0.50    6.00    --  110.00  75.00 126.69  192
 64  ω     80.00 177.00   0.50    6.00    --  110.00  77.00 -90.00  194
 65  ω     80.00 177.00   0.50    6.00    --  110.00  77.00-180.00  194
 66  ω     80.00 177.00   0.50    6.00    --  110.00  77.00  90.00  194
 67  ω     80.00 177.00   0.50    6.00    --  110.00  77.00 150.00  194
 68  ω     87.00 178.00   0.50    6.00    --  110.00  30.00 -60.00  182
 69  ω     87.00 178.00   0.50    6.00    --  110.00  61.00-180.00  182
 70  ω     87.00 178.00   0.50    6.00    --  110.00  61.00-150.00  182
 71  ω     38.00 112.00   0.50    6.00    --  110.00-125.00 -60.00  148
 72  ω     80.00 177.00   0.50    6.00    --  110.00  77.00  30.00  194
 73  ω     87.00 178.00   0.50    6.00    --  110.00  61.00  30.00  182
 74  ω     87.00 178.00   0.50    6.00    --  110.00  61.00   0.00  182
 75  ω     80.00 177.00   0.50    6.00    --  110.00  77.00-150.00  194
 76  ω     44.00 105.00   0.50    6.00    --  110.00 -77.00 -60.00  122
 77  ω     43.00  71.00   0.50    6.00    --  110.00 -61.00-180.00   56
 78  ω     43.00  71.00   0.50    6.00    --  110.00 -61.00  30.00   56
 79  ω     38.00 112.00   0.50    6.00    --  110.00-125.00 120.00  148
 80  ω     87.00 178.00   0.50    6.00    --  110.00  61.00 -30.00  182
 81  ω     80.00 176.00   0.50    6.00    --  110.00  75.00 110.48  192
 82  ω    -57.00 -12.00   0.50    1.50    --   -2.25 125.00  90.00   90
 83  ω    -13.00  36.00   0.50    1.50    --   -2.25 -94.00 -90.00   98
 84  ω     12.00 109.00   0.50    1.50    --   42.54  77.00 -30.00  194
 85  ω     23.00 112.00   0.50    1.50    --   42.54  57.00 -60.00  178
 86  ω     25.00 118.00   0.50    1.50    --   42.54  38.00-120.00  186
 87  ω     25.00 118.00   0.50    1.50    --   42.54  38.00 -60.00  186
 88  ω     23.00 112.00   0.50    1.50    --   42.54  57.00 150.00  178
 89  ω    -37.00  26.00   0.50    1.50    --   42.54 -19.00  30.00  126
 90  ω     23.00 112.00   0.50    1.50    --   42.54  57.00  90.00  178
 91  ω     -2.00  84.00   0.50    1.50    --   42.54 -99.00 -30.00  172
 92  ω     87.00 178.00   0.50    6.00    --  110.00  61.00  90.00  182
 93  ω     38.00 112.00   0.50    6.00    --  110.00-125.00-120.00  148
 94  ω     89.00 178.00   0.50    6.00    --  110.00  59.00-140.37  178
 95  ω     80.00 177.00   0.50    6.00    --  110.00  77.00 120.00  194
 96  ω     38.00 112.00   0.50    6.00    --  110.00-125.00  60.00  148
 97  ω     87.00 178.00   0.50    6.00    --  110.00  30.00 -30.00  182
 98  ω     82.00 175.00   0.50    6.00    --  110.00  71.00  63.44  186
 99  ω     83.00 175.00   0.50    6.00    --  110.00  69.00-128.45  184
100  ω     36.00 110.00   0.50    6.00    --  110.00-114.00-137.57  148
101  ω     41.00 143.00   0.50    6.00    --  110.00 -83.00 -54.93  204
102  ω     87.00 178.00   0.50    6.00    --  110.00  30.00-120.00  182
103  ω     87.00 178.00   0.50    6.00    --  110.00  30.00 -90.00  182
104  ω     35.00 109.00   0.50    6.00    --  110.00-109.00 123.39  148
105  ω     38.00 112.00   0.50    6.00    --  110.00-125.00 -30.00  148
106  ω     37.00 111.00   0.50    6.00    --  110.00-122.00 -24.14  148
107  ω     43.00  71.00   0.50    6.00    --  110.00 -61.00 -30.00   56
108  ω     94.00 178.00   0.50    6.00    --  110.00 125.00 150.00  168
109  ω     87.00 178.00   0.50    6.00    --  110.00  61.00 120.00  182
110  ω     87.00 178.00   0.50    6.00    --  110.00  30.00  90.00  182
111  ω     87.00 178.00   0.50    6.00    --  110.00  30.00 120.00  182
112  ω     87.00 178.00   0.50    6.00    --  110.00  30.00 150.00  182
113  ω     94.00 178.00   0.50    6.00    --  110.00 125.00 -30.00  168
114  ω     95.00 178.00   0.50    6.00    --  110.00  45.00   0.00  166
115  ω     87.00 178.00   0.50    6.00    --  110.00  30.00-150.00  182
116  ω     38.00 112.00   0.50    6.00    --  110.00-125.00 -90.00  148
117  ω     87.00 178.00   0.50    6.00    --  110.00  30.00   0.00  182
118  ω     87.00 178.00   0.50    6.00    --  110.00  61.00-115.60  182
119  ω     80.00 177.00   0.50    6.00    --  110.00  77.00   0.00  194
120  ω     83.00 175.00   0.50    6.00    --  110.00  69.00   5.96  184
121  ω     95.00 178.00   0.50    6.00    --  110.00  45.00  90.00  166
122  ω    -39.00 122.00   0.50    1.50    --   42.54   0.00  30.00  322
123  ω    -39.00 122.00   0.50    1.50    --   42.54   0.00-120.00  322
124  ω    -39.00 122.00   0.50    1.50    --   42.54   0.00 -60.00  322
125  ω     23.00 112.00   0.50    1.50    --   42.54  57.00-120.00  178
126  ω    -39.00 122.00   0.50    1.50    --   42.54   0.00 -30.00  322
127  ω    -39.00 122.00   0.50    1.50    --   42.54   0.00   0.00  322
128  ω    -39.00 122.00   0.50    1.50    --   42.54   0.00-180.00  322
129  ω    -39.00 122.00   0.50    1.50    --   42.54   0.00-150.00  322
130  ω    -39.00 122.00   0.50    1.50    --   42.54   0.00 -90.00  322
131  ω    -39.00 122.00   0.50    1.50    --   42.54   0.00  60.00  322
132  ω     38.00 112.00   0.50    6.00    --  110.00-125.00-150.00  148
133  ω     35.00 107.00   0.50    6.00    --  110.00 -94.00  60.00  144
134  ω     42.00 142.00   0.50    6.00    --  110.00 -81.00-155.50  200
135  ω     38.00 112.00   0.50    6.00    --  110.00-125.00 150.00  148
136  ω     87.00 178.00   0.50    6.00    --  110.00  30.00-180.00  182
137  ω     35.00 107.00   0.50    6.00    --  110.00 -94.00 -30.00  144
138  ω     35.00 107.00   0.50    6.00    --  110.00 -94.00 -90.00  144
139  ω     94.00 178.00   0.50    6.00    --  110.00 125.00  30.00  168
140  ω     94.00 178.00   0.50    6.00    --  110.00 125.00 -90.00  168
141  ω     94.00 178.00   0.50    6.00    --  110.00 125.00-180.00  168
142  ω     90.00 178.00   0.50    6.00    --  110.00  35.00  89.25  176
143  ω     85.00 175.00   0.50    6.00    --  110.00  67.00  89.98  180
144  ω     95.00 178.00   0.50    6.00    --  110.00  45.00 120.00  166
145  ω     95.00 178.00   0.50    6.00    --  110.00  45.00 -90.00  166
146  ω     29.00 178.00   0.50    6.00    --  110.00   0.00-180.00  298
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, Eiger 1M'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                5617
_reflns_number_total             5627
_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 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.84a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3 (Dolomanov et al., 2009)'
_computing_structure_refinement  'SHELXL 2018/3 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.564
_refine_diff_density_min         -0.519
_refine_diff_density_rms         0.056
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.148
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     364
_refine_ls_number_reflns         5627
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0307
_refine_ls_R_factor_gt           0.0307
_refine_ls_restrained_S_all      1.148
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0280P)²+3.0688P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0791
_refine_ls_wR_factor_ref         0.0791
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Free rotating group:
 O2(H2A,H2B), O1(H1A,H1B)
2.b Aromatic/amide H refined with riding coordinates:
 C6(H6), C8(H8), C21(H21), C23(H23), C7(H7), C24(H24), C12(H12), C14(H14),
 C9(H9), C17(H17), C10(H10), C16(H16), C11(H11), C15(H15)
2.c Idealised tetrahedral OH refined as rotating group:
 O4(H4), O3(H3)
;
_atom_sites_solution_hydrogens   mixed
_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
Mn1 Mn 0.49582(2) 0.67195(4) 0.63980(2) 0.01954(8) Uani 1 1 d . . . . .
P2 P 0.41776(2) 0.50759(6) 0.79675(3) 0.01846(10) Uani 1 1 d . . . . .
P1 P 0.41748(2) 0.33822(6) 0.54194(3) 0.02043(11) Uani 1 1 d . . . . .
S1 S 0.22446(3) 0.77715(8) 0.60362(4) 0.03731(14) Uani 1 1 d . . . . .
S2 S 0.14457(3) 0.45432(8) 0.64712(5) 0.04181(15) Uani 1 1 d . . . . .
S3 S 0.23073(3) 0.64516(9) 0.35679(4) 0.04567(17) Uani 1 1 d . . . . .
S4 S 0.14198(3) 0.34100(9) 0.39855(5) 0.04257(15) Uani 1 1 d . . . . .
O6 O 0.44691(6) 0.34103(17) 0.77869(9) 0.0229(3) Uani 1 1 d . . . . .
O5 O 0.44682(6) 0.65688(17) 0.75750(9) 0.0237(3) Uani 1 1 d . . . . .
O8 O 0.44810(7) 0.25417(18) 0.46762(9) 0.0259(3) Uani 1 1 d . . . . .
O4 O 0.41745(7) 0.52905(19) 0.89953(9) 0.0273(3) Uani 1 1 d . . . . .
H4 H 0.441267 0.602764 0.915797 0.041 Uiso 1 1 calc R U . . .
O3 O 0.42473(7) 0.21493(19) 0.62249(9) 0.0282(3) Uani 1 1 d . . . . .
H3 H 0.430834 0.268546 0.668085 0.042 Uiso 1 1 calc R U . . .
O7 O 0.43883(7) 0.50982(19) 0.56488(10) 0.0307(3) Uani 1 1 d . . . . .
C6 C 0.31447(9) 0.6250(3) 0.70407(13) 0.0258(4) Uani 1 1 d . . . . .
H6 H 0.337356 0.718203 0.691677 0.031 Uiso 1 1 calc R U . . .
C22 C 0.33777(9) 0.3438(3) 0.51025(13) 0.0246(4) Uani 1 1 d . . . . .
C5 C 0.34021(9) 0.4964(3) 0.75501(13) 0.0231(4) Uani 1 1 d . . . . .
C1 C 0.25442(9) 0.6145(3) 0.67150(14) 0.0270(4) Uani 1 1 d . . . . .
C8 C 0.30539(10) 0.3576(3) 0.77413(16) 0.0328(5) Uani 1 1 d . . . . .
H8 H 0.322436 0.271327 0.808232 0.039 Uiso 1 1 calc R U . . .
C21 C 0.31453(10) 0.4799(3) 0.46227(14) 0.0292(4) Uani 1 1 d . . . . .
H21 H 0.339087 0.571622 0.453462 0.035 Uiso 1 1 calc R U . . .
C2 C 0.22018(10) 0.4761(3) 0.69083(14) 0.0297(4) Uani 1 1 d . . . . .
C20 C 0.25505(10) 0.4803(3) 0.42737(14) 0.0305(5) Uani 1 1 d . . . . .
C23 C 0.29957(10) 0.2113(3) 0.52720(16) 0.0335(5) Uani 1 1 d . . . . .
H23 H 0.314372 0.120063 0.559642 0.040 Uiso 1 1 calc R U . . .
C19 C 0.21726(10) 0.3474(3) 0.44509(15) 0.0317(5) Uani 1 1 d . . . . .
C7 C 0.24554(11) 0.3481(3) 0.74248(16) 0.0354(5) Uani 1 1 d . . . . .
H7 H 0.222345 0.255992 0.755814 0.042 Uiso 1 1 calc R U . . .
C4 C 0.15135(10) 0.7977(3) 0.64225(15) 0.0346(5) Uani 1 1 d . . . . .
C3 C 0.11679(10) 0.6589(3) 0.65921(15) 0.0357(5) Uani 1 1 d . . . . .
C24 C 0.23943(11) 0.2153(3) 0.49570(17) 0.0374(5) Uani 1 1 d . . . . .
H24 H 0.213846 0.128194 0.508813 0.045 Uiso 1 1 calc R U . . .
C18 C 0.11963(11) 0.5510(3) 0.40906(15) 0.0377(5) Uani 1 1 d . . . . .
C13 C 0.15728(11) 0.6818(3) 0.39015(16) 0.0386(6) Uani 1 1 d . . . . .
C12 C 0.05808(12) 0.6794(4) 0.68465(18) 0.0463(7) Uani 1 1 d . . . . .
H12 H 0.035018 0.586689 0.697314 0.056 Uiso 1 1 calc R U . . .
C14 C 0.13721(14) 0.8456(4) 0.3969(2) 0.0515(7) Uani 1 1 d . . . . .
H14 H 0.162698 0.933713 0.384944 0.062 Uiso 1 1 calc R U . . .
C9 C 0.12754(12) 0.9564(4) 0.65241(18) 0.0445(6) Uani 1 1 d . . . . .
H9 H 0.151239 1.049709 0.643404 0.053 Uiso 1 1 calc R U . . .
C17 C 0.06184(12) 0.5849(4) 0.43520(18) 0.0488(7) Uani 1 1 d . . . . .
H17 H 0.036570 0.497610 0.449073 0.059 Uiso 1 1 calc R U . . .
C10 C 0.06885(13) 0.9765(4) 0.6758(2) 0.0541(8) Uani 1 1 d . . . . .
H10 H 0.052813 1.082900 0.681288 0.065 Uiso 1 1 calc R U . . .
C16 C 0.04211(14) 0.7473(5) 0.4405(2) 0.0591(9) Uani 1 1 d . . . . .
H16 H 0.003341 0.769091 0.457200 0.071 Uiso 1 1 calc R U . . .
C11 C 0.03423(13) 0.8378(5) 0.6910(2) 0.0555(8) Uani 1 1 d . . . . .
H11 H -0.005494 0.851057 0.705654 0.067 Uiso 1 1 calc R U . . .
C15 C 0.07953(15) 0.8776(5) 0.4212(2) 0.0587(8) Uani 1 1 d . . . . .
H15 H 0.065930 0.986998 0.424642 0.070 Uiso 1 1 calc R U . . .
O2 O 0.56169(10) 0.4705(3) 0.6740(2) 0.0688(8) Uani 1 1 d G . . A -1
H2A H 0.559135 0.359870 0.697573 0.066(10) Uiso 1 1 d G . . A -1
H2B H 0.564435 0.453885 0.612099 0.17(3) Uiso 1 1 d G . . A -1
O1 O 0.43245(8) 0.8711(2) 0.58988(11) 0.0349(4) Uani 1 1 d G . . B -1
H1A H 0.428105 0.872420 0.526829 0.108(16) Uiso 1 1 d G . . B -1
H1B H 0.434056 0.986632 0.606249 0.056(9) Uiso 1 1 d G . . B -1


_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
Mn1 O6 2.1869(14) 2_656 ?
Mn1 O5 2.1610(14) . ?
Mn1 O8 2.2018(14) 3_666 ?
Mn1 O7 2.0970(15) . ?
Mn1 O2 2.2171(19) . ?
Mn1 O1 2.2275(16) . ?
P2 O6 1.5164(14) . ?
P2 O5 1.5020(14) . ?
P2 O4 1.5750(14) . ?
P2 C5 1.797(2) . ?
P1 O8 1.5161(14) . ?
P1 O3 1.5748(15) . ?
P1 O7 1.4885(15) . ?
P1 C22 1.803(2) . ?
S1 C1 1.766(2) . ?
S1 C4 1.770(2) . ?
S2 C2 1.773(2) . ?
S2 C3 1.766(3) . ?
S3 C20 1.765(2) . ?
S3 C13 1.765(3) . ?
S4 C19 1.772(2) . ?
S4 C18 1.765(3) . ?
O4 H4 0.8200 . ?
O3 H3 0.8200 . ?
C6 H6 0.9300 . ?
C6 C5 1.389(3) . ?
C6 C1 1.393(3) . ?
C22 C21 1.392(3) . ?
C22 C23 1.394(3) . ?
C5 C8 1.396(3) . ?
C1 C2 1.387(3) . ?
C8 H8 0.9300 . ?
C8 C7 1.385(3) . ?
C21 H21 0.9300 . ?
C21 C20 1.390(3) . ?
C2 C7 1.389(3) . ?
C20 C19 1.393(3) . ?
C23 H23 0.9300 . ?
C23 C24 1.389(3) . ?
C19 C24 1.381(3) . ?
C7 H7 0.9300 . ?
C4 C3 1.385(4) . ?
C4 C9 1.390(4) . ?
C3 C12 1.394(3) . ?
C24 H24 0.9300 . ?
C18 C13 1.383(4) . ?
C18 C17 1.395(3) . ?
C13 C14 1.392(4) . ?
C12 H12 0.9300 . ?
C12 C11 1.381(4) . ?
C14 H14 0.9300 . ?
C14 C15 1.381(4) . ?
C9 H9 0.9300 . ?
C9 C10 1.383(4) . ?
C17 H17 0.9300 . ?
C17 C16 1.377(5) . ?
C10 H10 0.9300 . ?
C10 C11 1.379(5) . ?
C16 H16 0.9300 . ?
C16 C15 1.378(5) . ?
C11 H11 0.9300 . ?
C15 H15 0.9300 . ?
O2 H2A 0.9591 . ?
O2 H2B 0.9584 . ?
O1 H1A 0.9585 . ?
O1 H1B 0.9586 . ?

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
O6 Mn1 O8 85.35(5) 2_656 3_666 ?
O6 Mn1 O2 88.18(9) 2_656 . ?
O6 Mn1 O1 94.58(6) 2_656 . ?
O5 Mn1 O6 82.52(5) . 2_656 ?
O5 Mn1 O8 166.41(5) . 3_666 ?
O5 Mn1 O2 97.18(8) . . ?
O5 Mn1 O1 88.95(6) . . ?
O8 Mn1 O2 88.49(7) 3_666 . ?
O8 Mn1 O1 85.95(6) 3_666 . ?
O7 Mn1 O6 178.10(6) . 2_656 ?
O7 Mn1 O5 95.61(6) . . ?
O7 Mn1 O8 96.49(6) . 3_666 ?
O7 Mn1 O2 92.37(9) . . ?
O7 Mn1 O1 85.06(6) . . ?
O2 Mn1 O1 173.57(9) . . ?
O6 P2 O4 107.85(8) . . ?
O6 P2 C5 107.59(9) . . ?
O5 P2 O6 115.41(8) . . ?
O5 P2 O4 109.81(8) . . ?
O5 P2 C5 109.01(9) . . ?
O4 P2 C5 106.82(9) . . ?
O8 P1 O3 105.97(8) . . ?
O8 P1 C22 106.99(9) . . ?
O3 P1 C22 105.76(9) . . ?
O7 P1 O8 115.72(9) . . ?
O7 P1 O3 112.48(9) . . ?
O7 P1 C22 109.34(9) . . ?
C1 S1 C4 101.07(11) . . ?
C3 S2 C2 101.42(11) . . ?
C13 S3 C20 101.56(11) . . ?
C18 S4 C19 101.51(11) . . ?
P2 O6 Mn1 132.95(8) . 2_646 ?
P2 O5 Mn1 128.89(8) . . ?
P1 O8 Mn1 137.64(9) . 3_666 ?
P2 O4 H4 109.5 . . ?
P1 O3 H3 109.5 . . ?
P1 O7 Mn1 150.60(10) . . ?
C5 C6 H6 119.9 . . ?
C5 C6 C1 120.1(2) . . ?
C1 C6 H6 119.9 . . ?
C21 C22 P1 118.86(16) . . ?
C21 C22 C23 119.0(2) . . ?
C23 C22 P1 121.99(17) . . ?
C6 C5 P2 120.60(16) . . ?
C6 C5 C8 119.62(19) . . ?
C8 C5 P2 119.78(16) . . ?
C6 C1 S1 118.54(17) . . ?
C2 C1 S1 121.59(16) . . ?
C2 C1 C6 119.85(19) . . ?
C5 C8 H8 119.9 . . ?
C7 C8 C5 120.2(2) . . ?
C7 C8 H8 119.9 . . ?
C22 C21 H21 119.6 . . ?
C20 C21 C22 120.8(2) . . ?
C20 C21 H21 119.6 . . ?
C1 C2 S2 121.18(17) . . ?
C1 C2 C7 120.2(2) . . ?
C7 C2 S2 118.55(18) . . ?
C21 C20 S3 118.61(18) . . ?
C21 C20 C19 119.5(2) . . ?
C19 C20 S3 121.77(17) . . ?
C22 C23 H23 120.0 . . ?
C24 C23 C22 120.1(2) . . ?
C24 C23 H23 120.0 . . ?
C20 C19 S4 120.57(18) . . ?
C24 C19 S4 119.52(18) . . ?
C24 C19 C20 119.8(2) . . ?
C8 C7 C2 120.0(2) . . ?
C8 C7 H7 120.0 . . ?
C2 C7 H7 120.0 . . ?
C3 C4 S1 121.26(19) . . ?
C3 C4 C9 119.6(2) . . ?
C9 C4 S1 119.1(2) . . ?
C4 C3 S2 121.62(18) . . ?
C4 C3 C12 119.8(2) . . ?
C12 C3 S2 118.6(2) . . ?
C23 C24 H24 119.7 . . ?
C19 C24 C23 120.6(2) . . ?
C19 C24 H24 119.7 . . ?
C13 C18 S4 121.76(19) . . ?
C13 C18 C17 119.5(3) . . ?
C17 C18 S4 118.8(2) . . ?
C18 C13 S3 121.1(2) . . ?
C18 C13 C14 119.9(3) . . ?
C14 C13 S3 119.0(2) . . ?
C3 C12 H12 120.1 . . ?
C11 C12 C3 119.9(3) . . ?
C11 C12 H12 120.1 . . ?
C13 C14 H14 119.9 . . ?
C15 C14 C13 120.1(3) . . ?
C15 C14 H14 119.9 . . ?
C4 C9 H9 119.8 . . ?
C10 C9 C4 120.5(3) . . ?
C10 C9 H9 119.8 . . ?
C18 C17 H17 119.9 . . ?
C16 C17 C18 120.2(3) . . ?
C16 C17 H17 119.9 . . ?
C9 C10 H10 120.2 . . ?
C11 C10 C9 119.6(3) . . ?
C11 C10 H10 120.2 . . ?
C17 C16 H16 119.8 . . ?
C17 C16 C15 120.3(3) . . ?
C15 C16 H16 119.8 . . ?
C12 C11 H11 119.7 . . ?
C10 C11 C12 120.5(3) . . ?
C10 C11 H11 119.7 . . ?
C14 C15 H15 120.0 . . ?
C16 C15 C14 120.0(3) . . ?
C16 C15 H15 120.0 . . ?
Mn1 O2 H2A 134.9 . . ?
Mn1 O2 H2B 87.4 . . ?
H2A O2 H2B 104.4 . . ?
Mn1 O1 H1A 111.6 . . ?
Mn1 O1 H1B 126.3 . . ?
H1A O1 H1B 104.4 . . ?

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
P2 C5 C8 C7 179.81(19) . . . . ?
P1 C22 C21 C20 172.18(17) . . . . ?
P1 C22 C23 C24 -175.01(19) . . . . ?
S1 C1 C2 S2 0.8(3) . . . . ?
S1 C1 C2 C7 178.25(18) . . . . ?
S1 C4 C3 S2 2.3(3) . . . . ?
S1 C4 C3 C12 -176.27(19) . . . . ?
S1 C4 C9 C10 174.9(2) . . . . ?
S2 C2 C7 C8 176.91(19) . . . . ?
S2 C3 C12 C11 -177.3(2) . . . . ?
S3 C20 C19 S4 -1.3(3) . . . . ?
S3 C20 C19 C24 175.44(19) . . . . ?
S3 C13 C14 C15 178.8(2) . . . . ?
S4 C19 C24 C23 174.96(19) . . . . ?
S4 C18 C13 S3 -1.5(3) . . . . ?
S4 C18 C13 C14 178.1(2) . . . . ?
S4 C18 C17 C16 -177.3(2) . . . . ?
O6 P2 O5 Mn1 28.97(13) . . . . ?
O6 P2 C5 C6 -133.25(17) . . . . ?
O6 P2 C5 C8 47.0(2) . . . . ?
O5 P2 O6 Mn1 105.62(12) . . . 2_646 ?
O5 P2 C5 C6 -7.42(19) . . . . ?
O5 P2 C5 C8 172.81(17) . . . . ?
O8 P1 O7 Mn1 -92.4(2) . . . . ?
O8 P1 C22 C21 -88.91(18) . . . . ?
O8 P1 C22 C23 86.72(19) . . . . ?
O4 P2 O6 Mn1 -17.55(14) . . . 2_646 ?
O4 P2 O5 Mn1 151.09(10) . . . . ?
O4 P2 C5 C6 111.18(17) . . . . ?
O4 P2 C5 C8 -68.60(19) . . . . ?
O3 P1 O8 Mn1 -142.01(12) . . . 3_666 ?
O3 P1 O7 Mn1 29.5(2) . . . . ?
O3 P1 C22 C21 158.44(16) . . . . ?
O3 P1 C22 C23 -25.9(2) . . . . ?
O7 P1 O8 Mn1 -16.62(17) . . . 3_666 ?
O7 P1 C22 C21 37.11(19) . . . . ?
O7 P1 C22 C23 -147.26(18) . . . . ?
C6 C5 C8 C7 0.0(3) . . . . ?
C6 C1 C2 S2 -177.50(17) . . . . ?
C6 C1 C2 C7 0.0(3) . . . . ?
C22 P1 O8 Mn1 105.48(14) . . . 3_666 ?
C22 P1 O7 Mn1 146.71(19) . . . . ?
C22 C21 C20 S3 -172.84(17) . . . . ?
C22 C21 C20 C19 3.9(3) . . . . ?
C22 C23 C24 C19 2.1(4) . . . . ?
C5 P2 O6 Mn1 -132.45(11) . . . 2_646 ?
C5 P2 O5 Mn1 -92.21(12) . . . . ?
C5 C6 C1 S1 -177.64(16) . . . . ?
C5 C6 C1 C2 0.7(3) . . . . ?
C5 C8 C7 C2 0.6(4) . . . . ?
C1 S1 C4 C3 -43.4(2) . . . . ?
C1 S1 C4 C9 139.1(2) . . . . ?
C1 C6 C5 P2 179.53(16) . . . . ?
C1 C6 C5 C8 -0.7(3) . . . . ?
C1 C2 C7 C8 -0.6(4) . . . . ?
C21 C22 C23 C24 0.6(3) . . . . ?
C21 C20 C19 S4 -177.88(17) . . . . ?
C21 C20 C19 C24 -1.2(3) . . . . ?
C2 S2 C3 C4 40.4(2) . . . . ?
C2 S2 C3 C12 -141.0(2) . . . . ?
C20 S3 C13 C18 -41.0(2) . . . . ?
C20 S3 C13 C14 139.4(2) . . . . ?
C20 C19 C24 C23 -1.8(4) . . . . ?
C23 C22 C21 C20 -3.6(3) . . . . ?
C19 S4 C18 C13 42.9(2) . . . . ?
C19 S4 C18 C17 -138.7(2) . . . . ?
C4 S1 C1 C6 -140.04(18) . . . . ?
C4 S1 C1 C2 41.7(2) . . . . ?
C4 C3 C12 C11 1.4(4) . . . . ?
C4 C9 C10 C11 1.4(4) . . . . ?
C3 S2 C2 C1 -42.1(2) . . . . ?
C3 S2 C2 C7 140.4(2) . . . . ?
C3 C4 C9 C10 -2.6(4) . . . . ?
C3 C12 C11 C10 -2.6(4) . . . . ?
C18 S4 C19 C20 -41.0(2) . . . . ?
C18 S4 C19 C24 142.2(2) . . . . ?
C18 C13 C14 C15 -0.9(4) . . . . ?
C18 C17 C16 C15 -0.9(4) . . . . ?
C13 S3 C20 C21 -140.83(19) . . . . ?
C13 S3 C20 C19 42.5(2) . . . . ?
C13 C18 C17 C16 1.2(4) . . . . ?
C13 C14 C15 C16 1.2(4) . . . . ?
C9 C4 C3 S2 179.81(19) . . . . ?
C9 C4 C3 C12 1.2(4) . . . . ?
C9 C10 C11 C12 1.2(5) . . . . ?
C17 C18 C13 S3 -179.97(19) . . . . ?
C17 C18 C13 C14 -0.3(4) . . . . ?
C17 C16 C15 C14 -0.3(5) . . . . ?

_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
;
