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

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

data_1
_audit_block_doi                 10.5517/ccdc.csd.cc288d32
_database_code_depnum_ccdc_archive 'CCDC 2093433'
loop_
_citation_id
_citation_doi
_citation_year
1 10.1039/D1CE00873K 2021
loop_
_audit_author_name
_audit_author_address
'Zhien Lin'
;Sichuan University
China
;
_audit_update_record             
;
2021-06-30 deposited with the CCDC.	2022-01-03 downloaded from the CCDC.
;
_audit_creation_date             2021-05-11
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C7 H6 In N O8 P'
_chemical_formula_sum            'C7 H6 In N O8 P'
_chemical_formula_weight         377.92
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C14  H12  In2  N2  O16  P2  '
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'
In In 0.0822 5.0449 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.6218(4)
_cell_length_b                   9.3168(8)
_cell_length_c                   9.4721(7)
_cell_angle_alpha                114.317(7)
_cell_angle_beta                 95.498(6)
_cell_angle_gamma                105.293(7)
_cell_volume                     499.59(7)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3024
_cell_measurement_temperature    290.77(11)
_cell_measurement_theta_max      71.3860
_cell_measurement_theta_min      5.2450
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    20.864
_exptl_absorpt_correction_T_max  0.189
_exptl_absorpt_correction_T_min  0.015
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (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 colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.512
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             366
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 6 -2 0.1172
3 -1 -4 0.1460
-4 1 2 0.1566
0 2 -6 0.0932
4 -2 0 0.1285
1 1 4 0.1295
0 -1 -5 0.0772
3 1 1 0.1430
0 -6 4 0.1285
0 -4 6 0.0992
3 2 -4 0.1631
0 4 2 0.0925
1 -5 5 0.1054

_exptl_crystal_size_max          0.325
_exptl_crystal_size_mid          0.263
_exptl_crystal_size_min          0.206
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
0.0031 5.9901 -1.9947 0.7985 0.6463 0.1574
2.9951 -0.9972 -3.9973 -0.1964 -0.1102 0.9249
-3.9944 0.9980 1.9993 0.3690 -0.3340 -0.8203
-0.0001 1.9986 -5.9933 0.5008 -0.4736 0.7052
3.9942 -1.9970 -0.0018 -0.5754 0.4416 0.5901
1.0003 0.9967 3.9967 -0.1421 0.8533 -0.3639
-0.0016 -0.9965 -4.9960 0.1015 -0.7968 0.6265
2.9973 0.9975 0.9992 -0.1794 0.8373 0.2838
-0.0027 -5.9908 3.9929 -0.8865 -0.3879 -0.4021
-0.0011 -3.9950 5.9922 -0.7376 0.1721 -0.6761
2.9968 1.9975 -3.9956 0.1589 0.3421 0.8812
0.0027 3.9922 2.0004 0.3857 0.8615 -0.3031
0.9970 -4.9930 4.9924 -0.8967 0.0779 -0.3988

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0658
_diffrn_reflns_av_unetI/netI     0.0561
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            5120
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.050
_diffrn_reflns_theta_max         67.050
_diffrn_reflns_theta_min         5.269
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      290.77(11)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -54.00  33.00   1.00    1.00    --  -35.23  57.00 120.00   87
  2  ω    -64.00  34.00   1.00    1.00    --  -35.23  77.00-120.00   98
  3  ω     13.00 106.00   1.00    1.00    --   35.23  38.00-150.00   93
  4  ω     17.00 104.00   1.00    1.00    --   35.23  57.00 -30.00   87
  5  ω     17.00 104.00   1.00    1.00    --   35.23  57.00  30.00   87
  6  ω     17.00 104.00   1.00    1.00    --   35.23  57.00   0.00   87
  7  ω     17.00 104.00   1.00    1.00    --   35.23  57.00 -60.00   87
  8  ω     23.00  90.00   1.00    1.00    --   35.23-125.00 120.00   67
  9  ω     87.00 177.00   1.00    1.00    --  106.90  45.00   0.00   90
 10  ω     37.00 110.00   1.00    1.00    --  106.90 -94.00 -90.00   73
 11  ω    100.00 178.00   1.00    1.00    --  106.90 111.00-180.00   78
 12  ω     39.00 127.00   1.00    1.00    --  106.90 -61.00 -90.00   88
 13  ω     36.00 113.00   1.00    1.00    --  106.90-111.00  30.00   77
 14  ω     36.00 113.00   1.00    1.00    --  106.90-111.00-180.00   77
 15  ω     87.00 177.00   1.00    1.00    --  106.90  45.00-120.00   90
 16  ω     39.00 127.00   1.00    1.00    --  106.90 -61.00  30.00   88
 17  ω    100.00 178.00   1.00    1.00    --  106.90 111.00  60.00   78
 18  ω     37.00 110.00   1.00    1.00    --  106.90 -94.00-120.00   73
 19  ω     36.00 113.00   1.00    1.00    --  106.90-111.00  90.00   77
 20  ω     87.00 175.00   1.00    1.00    --  106.90  61.00 -90.00   88
 21  ω     87.00 177.00   1.00    1.00    --  106.90  45.00-180.00   90
 22  ω     39.00 127.00   1.00    1.00    --  106.90 -61.00 150.00   88
 23  ω     81.00 178.00   1.00    1.00    --  106.90  30.00 120.00   97
 24  ω    -57.00  35.00   1.00    1.00    --  -35.23  38.00-150.00   92
 25  ω      7.00 104.00   1.00    1.00    --   35.23  77.00-150.00   97
 26  ω    -33.00  54.00   1.00    1.00    --   35.23 -57.00 -90.00   87
 27  ω    -33.00  54.00   1.00    1.00    --   35.23 -57.00 -30.00   87
 28  ω      7.00 104.00   1.00    1.00    --   35.23  77.00  30.00   97
 29  ω     17.00 104.00   1.00    1.00    --   35.23  57.00 120.00   87
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0847181000
_diffrn_orient_matrix_UB_12      0.1187139000
_diffrn_orient_matrix_UB_13      -0.0439676000
_diffrn_orient_matrix_UB_21      0.1860427000
_diffrn_orient_matrix_UB_22      0.1508631000
_diffrn_orient_matrix_UB_23      0.1293295000
_diffrn_orient_matrix_UB_31      0.1403902000
_diffrn_orient_matrix_UB_32      -0.0146083000
_diffrn_orient_matrix_UB_33      -0.1225365000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1713
_reflns_number_total             1781
_reflns_odcompleteness_completeness 100.00
_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 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (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         1.363
_refine_diff_density_min         -1.671
_refine_diff_density_rms         0.267
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.088
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         1781
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0501
_refine_ls_R_factor_gt           0.0489
_refine_ls_restrained_S_all      1.088
_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)+(0.0923P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1260
_refine_ls_wR_factor_ref         0.1273
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C2(H2), C3(H3), C5(H5), C6(H6)
2.b Idealised tetrahedral OH refined as rotating group:
 O4(H4)
;
_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
In1 In 0.32161(6) 0.64678(5) 0.40794(4) 0.0136(2) Uani 1 1 d . . . . .
P1 P 0.2243(2) 0.4557(2) 0.65372(17) 0.0136(4) Uani 1 1 d . . . . .
O1 O 0.2477(7) 0.5873(6) 0.5949(5) 0.0192(10) Uani 1 1 d . . . . .
O2 O 0.3594(7) 0.3463(7) 0.5919(6) 0.0243(11) Uani 1 1 d . . . . .
O3 O -0.0058(7) 0.3399(6) 0.6122(6) 0.0211(10) Uani 1 1 d . . . . .
O4 O 0.3014(9) 0.5665(6) 0.8390(5) 0.0251(11) Uani 1 1 d . . . . .
H4 H 0.2596 0.5091 0.8837 0.038 Uiso 1 1 calc GR . . . .
O5 O 0.4755(8) 0.8972(6) 0.6190(5) 0.0204(10) Uani 1 1 d . . . . .
O6 O 0.6194(8) 1.1670(6) 0.6882(5) 0.0211(10) Uani 1 1 d . . . . .
O7 O 0.2254(8) 0.3863(6) 0.2464(5) 0.0217(10) Uani 1 1 d . . . . .
O8 O 0.2328(11) 0.4825(7) 0.0677(6) 0.0359(14) Uani 1 1 d . . . . .
N1 N 0.1287(11) -0.1212(8) -0.2351(8) 0.0361(17) Uani 1 1 d . . . . .
H1 H 0.1095 -0.2219 -0.3043 0.043 Uiso 1 1 calc R . . . .
C1 C 0.5302(10) 1.0191(8) 0.5880(8) 0.0157(12) Uani 1 1 d . . . . .
C2 C 0.2359(12) -0.0683(10) -0.0863(11) 0.0313(17) Uani 1 1 d . . . . .
H2 H 0.2886 -0.1390 -0.0592 0.038 Uiso 1 1 calc R . . . .
C3 C 0.2672(12) 0.0919(10) 0.0261(9) 0.0267(15) Uani 1 1 d . . . . .
H3 H 0.3403 0.1312 0.1307 0.032 Uiso 1 1 calc R . . . .
C4 C 0.1876(11) 0.1932(9) -0.0196(8) 0.0210(14) Uani 1 1 d . . . . .
C5 C 0.0807(14) 0.1341(10) -0.1738(9) 0.0309(17) Uani 1 1 d . . . . .
H5 H 0.0287 0.2023 -0.2056 0.037 Uiso 1 1 calc R . . . .
C6 C 0.0516(15) -0.0278(11) -0.2809(9) 0.038(2) Uani 1 1 d . . . . .
H6 H -0.0228 -0.0707 -0.3858 0.046 Uiso 1 1 calc R . . . .
C7 C 0.2179(12) 0.3669(8) 0.1032(8) 0.0221(15) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
In1 O1 2.124(4) . ?
In1 O2 2.096(5) 2_666 ?
In1 O3 2.123(4) 2_566 ?
In1 O5 2.234(5) . ?
In1 O6 2.237(4) 2_676 ?
In1 O7 2.139(5) . ?
P1 O1 1.522(5) . ?
P1 O2 1.507(5) . ?
P1 O3 1.520(5) . ?
P1 O4 1.570(5) . ?
O2 In1 2.096(5) 2_666 ?
O3 In1 2.123(4) 2_566 ?
O4 H4 0.8200 . ?
O5 C1 1.259(8) . ?
O6 In1 2.237(4) 2_676 ?
O6 C1 1.238(8) . ?
O7 C7 1.287(8) . ?
O8 C7 1.238(8) . ?
N1 H1 0.8600 . ?
N1 C2 1.336(12) . ?
N1 C6 1.308(12) . ?
C1 C1 1.541(13) 2_676 ?
C2 H2 0.9300 . ?
C2 C3 1.375(11) . ?
C3 H3 0.9300 . ?
C3 C4 1.383(10) . ?
C4 C5 1.368(10) . ?
C4 C7 1.498(9) . ?
C5 H5 0.9300 . ?
C5 C6 1.375(12) . ?
C6 H6 0.9300 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 In1 O5 79.40(17) . . ?
O1 In1 O6 148.83(18) . 2_676 ?
O1 In1 O7 90.01(18) . . ?
O2 In1 O1 105.05(19) 2_666 . ?
O2 In1 O3 171.42(19) 2_666 2_566 ?
O2 In1 O5 83.5(2) 2_666 . ?
O2 In1 O6 87.9(2) 2_666 2_676 ?
O2 In1 O7 87.3(2) 2_666 . ?
O3 In1 O1 83.14(19) 2_566 . ?
O3 In1 O5 95.68(19) 2_566 . ?
O3 In1 O6 83.66(19) 2_566 2_676 ?
O3 In1 O7 95.4(2) 2_566 . ?
O5 In1 O6 73.98(16) . 2_676 ?
O7 In1 O5 163.65(19) . . ?
O7 In1 O6 119.28(17) . 2_676 ?
O1 P1 O4 101.8(3) . . ?
O2 P1 O1 113.5(3) . . ?
O2 P1 O3 106.9(3) . . ?
O2 P1 O4 111.4(3) . . ?
O3 P1 O1 113.7(3) . . ?
O3 P1 O4 109.6(3) . . ?
P1 O1 In1 144.6(3) . . ?
P1 O2 In1 142.6(3) . 2_666 ?
P1 O3 In1 138.3(3) . 2_566 ?
P1 O4 H4 109.5 . . ?
C1 O5 In1 115.5(4) . . ?
C1 O6 In1 115.6(4) . 2_676 ?
C7 O7 In1 109.6(4) . . ?
C2 N1 H1 118.3 . . ?
C6 N1 H1 118.3 . . ?
C6 N1 C2 123.3(7) . . ?
O5 C1 C1 116.9(7) . 2_676 ?
O6 C1 O5 125.2(6) . . ?
O6 C1 C1 117.9(7) . 2_676 ?
N1 C2 H2 120.4 . . ?
N1 C2 C3 119.2(7) . . ?
C3 C2 H2 120.4 . . ?
C2 C3 H3 120.7 . . ?
C2 C3 C4 118.6(7) . . ?
C4 C3 H3 120.7 . . ?
C3 C4 C7 118.8(6) . . ?
C5 C4 C3 120.2(7) . . ?
C5 C4 C7 121.0(7) . . ?
C4 C5 H5 120.6 . . ?
C4 C5 C6 118.8(8) . . ?
C6 C5 H5 120.6 . . ?
N1 C6 C5 119.9(8) . . ?
N1 C6 H6 120.0 . . ?
C5 C6 H6 120.0 . . ?
O7 C7 C4 115.4(6) . . ?
O8 C7 O7 122.8(6) . . ?
O8 C7 C4 121.8(6) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O4 H4 O8 0.82 1.88 2.629(7) 151.8 1_556
N1 H1 O1 0.86 2.13 2.891(8) 147.2 1_544

_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
- Detector area scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 3.058
_oxdiff_exptl_absorpt_empirical_full_min 0.673
####################################################################### 
# 
# 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_2
_database_code_depnum_ccdc_archive 'CCDC 2128159'
loop_
_audit_author_name
_audit_author_address
'Zhien Lin'
;Sichuan Univerty
China
;
_audit_update_record             
;
2021-12-13 deposited with the CCDC.	2022-01-03 downloaded from the CCDC.
;
_audit_creation_date             2021-12-10
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C H3 Fe O10 P2, C4 H7 N2'
_chemical_formula_sum            'C5 H10 Fe N2 O10 P2'
_chemical_formula_weight         375.94
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C20  H40  Fe4  N8  O40  P8  '
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'
Fe Fe -1.1336 3.1974 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.2955 0.4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   9.1586(2)
_cell_length_b                   10.0083(3)
_cell_length_c                   12.7498(4)
_cell_angle_alpha                90
_cell_angle_beta                 94.467(2)
_cell_angle_gamma                90
_cell_volume                     1165.12(6)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2678
_cell_measurement_temperature    295.7(5)
_cell_measurement_theta_max      71.2290
_cell_measurement_theta_min      4.8130
_shelx_estimated_absorpt_T_max   0.120
_shelx_estimated_absorpt_T_min   0.031
_exptl_absorpt_coefficient_mu    13.596
_exptl_absorpt_correction_T_max  0.215
_exptl_absorpt_correction_T_min  0.020
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.46e (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 yellow'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    2.143
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             760
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
5 0 -6 0.1596
2 6 1 0.3668
-5 1 6 0.1881
0 -6 -3 0.3853
3 0 -7 0.1482
-3 0 7 0.1729
1 0 -8 0.1261
0 -4 -6 0.3287
-1 0 8 0.1452
-2 0 -8 0.1760
2 0 8 0.1198
-5 0 -4 0.1978
-3 5 -2 0.4044
5 0 4 0.0835
-1 -6 -1 0.3708
-6 0 1 0.1591
-1 -5 6 0.2288

_exptl_crystal_size_max          0.83
_exptl_crystal_size_mid          0.313
_exptl_crystal_size_min          0.271
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
4.9951 0.0043 -5.9977 -0.6735 -0.8279 -0.0671
2.0055 5.9940 1.0038 -0.0339 -0.1173 -0.9865
-4.9939 0.9952 5.9989 0.6454 0.8626 -0.0801
-0.0074 -5.9928 -3.0034 -0.1879 -0.2131 0.9507
2.9963 0.0068 -6.9947 -0.8086 -0.5027 0.0361
-2.9963 -0.0068 6.9947 0.8086 0.5027 -0.0361
0.9975 0.0094 -7.9918 -0.9436 -0.1775 0.1394
-0.0058 -3.9901 -5.9977 -0.6011 -0.1491 0.7237
-0.9975 -0.0094 7.9918 0.9436 0.1775 -0.1394
-2.0003 0.0114 -7.9890 -0.9677 0.3129 0.2606
2.0003 -0.0114 7.9890 0.9677 -0.3129 -0.2606
-4.9973 0.0083 -3.9908 -0.5160 0.8104 0.2918
-2.9927 5.0016 -1.9893 -0.4029 0.6602 -0.5699
4.9973 -0.0083 3.9908 0.5160 -0.8104 -0.2918
-1.0062 -5.9946 -1.0047 0.0420 -0.0462 0.9461
-5.9954 0.0027 1.0044 0.0707 0.9826 0.2199
-1.0036 -5.0040 5.9884 0.8465 0.0008 0.6416

_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0778
_diffrn_reflns_av_unetI/netI     0.0548
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            6287
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        67.041
_diffrn_reflns_theta_max         67.041
_diffrn_reflns_theta_min         4.843
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      295.7(5)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 15.9595
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -53.00  33.00   1.00    1.76    --  -34.98  57.00-120.00   86
  2  ω   -106.00  36.00   1.00    1.76    --  -34.98   0.00-150.00  142
  3  ω      1.00  75.00   1.00    1.76    --   34.98 -99.00 150.00   74
  4  ω     23.00  90.00   1.00    1.76    --   34.98-125.00 -60.00   67
  5  ω     16.00 103.00   1.00    1.76    --   34.98  57.00-150.00   87
  6  ω     23.00  90.00   1.00    1.76    --   34.98-125.00 150.00   67
  7  ω     87.00 177.00   1.00    7.04    --  106.90  45.00-180.00   90
  8  ω     87.00 175.00   1.00    7.04    --  106.90  61.00 -90.00   88
  9  ω     35.00 133.00   1.00    7.04    --  106.90 -30.00 -90.00   98
 10  ω     37.00 110.00   1.00    7.04    --  106.90 -94.00 -60.00   73
 11  ω     35.00 133.00   1.00    7.04    --  106.90 -30.00   0.00   98
 12  ω    100.00 178.00   1.00    7.04    --  106.90 111.00  90.00   78
 13  ω     38.00 136.00   1.00    7.04    --  106.90 -77.00   0.00   98
 14  ω   -103.00 -16.00   1.00    1.76    --  -34.98 -57.00  90.00   87
 15  ω      6.00  86.00   1.00    1.76    --   34.98  77.00   0.00   80
 16  ω    -36.00  57.00   1.00    1.76    --   34.98 -38.00 -60.00   93
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'New Gemini, Dual, Cu at home/near, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0081388000
_diffrn_orient_matrix_UB_12      -0.0283248000
_diffrn_orient_matrix_UB_13      0.1190567000
_diffrn_orient_matrix_UB_21      -0.1635707000
_diffrn_orient_matrix_UB_22      0.0348484000
_diffrn_orient_matrix_UB_23      0.0018370000
_diffrn_orient_matrix_UB_31      -0.0405376000
_diffrn_orient_matrix_UB_32      -0.1472199000
_diffrn_orient_matrix_UB_33      -0.0226736000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Cu) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1911
_reflns_number_total             2071
_reflns_odcompleteness_completeness 100.00
_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 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.46e (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.46e (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         1.042
_refine_diff_density_min         -0.831
_refine_diff_density_rms         0.178
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.080
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     185
_refine_ls_number_reflns         2071
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0661
_refine_ls_R_factor_gt           0.0625
_refine_ls_restrained_S_all      1.080
_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)+(0.1154P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1566
_refine_ls_wR_factor_ref         0.1620
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All N(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 N1(H1), C3(H3A), C4(H4), C5(H5)
2.b Idealised Me refined as rotating group:
 C2(H2A,H2B,H2C)
2.c Idealised tetrahedral OH refined as rotating group:
 O3(H3), O7(H7), O8(H8)
;
_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
Fe1 Fe 0.50619(7) 0.77386(7) 0.52406(5) 0.0165(3) Uani 1 1 d . . . . .
P1 P 0.24238(11) 1.00048(10) 0.48766(7) 0.0175(3) Uani 1 1 d . . . . .
P2 P 0.53785(12) 0.85723(12) 0.26738(8) 0.0200(3) Uani 1 1 d . . . . .
O1 O 0.3420(3) 0.8918(3) 0.5351(3) 0.0257(7) Uani 1 1 d . . . . .
O2 O 0.1534(3) 1.0607(4) 0.5710(2) 0.0251(7) Uani 1 1 d . . . . .
O3 O 0.1339(3) 0.9380(4) 0.3994(3) 0.0284(8) Uani 1 1 d . . . . .
H3 H 0.0496 0.9464 0.4157 0.043 Uiso 1 1 calc GR . . . .
O4 O 0.3333(3) 1.1042(3) 0.4329(2) 0.0233(7) Uani 1 1 d . . . . .
O5 O 0.5140(4) 0.8008(4) 0.3734(3) 0.0303(8) Uani 1 1 d . . . . .
O6 O 0.4938(4) 0.7603(3) 0.1801(2) 0.0221(7) Uani 1 1 d . . . . .
O7 O 0.6972(4) 0.9024(5) 0.2603(3) 0.0376(9) Uani 1 1 d . . . . .
H7 H 0.7431 0.8917 0.3175 0.056 Uiso 1 1 calc GR . . . .
O8 O 0.4364(5) 0.9809(4) 0.2433(3) 0.0409(10) Uani 1 1 d . . . . .
H8 H 0.4308 1.0247 0.2972 0.061 Uiso 1 1 calc GR . . . .
O9 O 0.6464(3) 0.6094(3) 0.5191(2) 0.0221(7) Uani 1 1 d . . . . .
O10 O 0.6433(3) 0.3868(3) 0.5041(2) 0.0226(7) Uani 1 1 d . . . . .
C1 C 0.5844(5) 0.4994(4) 0.5064(3) 0.0185(9) Uani 1 1 d . . . . .
N1 N 0.1928(5) 0.7148(6) 0.2117(5) 0.0490(15) Uani 1 1 d . . . . .
H1 H 0.2852 0.7185 0.2040 0.059 Uiso 1 1 calc R . . . .
N2 N -0.0086(5) 0.6739(5) 0.2770(4) 0.0365(10) Uani 1 1 d . . . . .
C2 C -0.1164(8) 0.6234(7) 0.3471(6) 0.0563(18) Uani 1 1 d . . . . .
H2A H -0.1578 0.6971 0.3828 0.085 Uiso 1 1 calc GR . . . .
H2B H -0.0689 0.5637 0.3979 0.085 Uiso 1 1 calc GR . . . .
H2C H -0.1927 0.5766 0.3063 0.085 Uiso 1 1 calc GR . . . .
C3 C 0.1333(6) 0.6601(7) 0.2912(5) 0.0449(15) Uani 1 1 d . . . . .
H3A H 0.1836 0.6184 0.3483 0.054 Uiso 1 1 calc R . . . .
C4 C 0.0860(8) 0.7645(7) 0.1434(6) 0.0475(15) Uani 1 1 d . . . . .
H4 H 0.0986 0.8076 0.0801 0.057 Uiso 1 1 calc R . . . .
C5 C -0.0406(7) 0.7398(7) 0.1841(5) 0.0409(13) Uani 1 1 d . . . . .
H5 H -0.1334 0.7630 0.1549 0.049 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
Fe1 O1 1.925(3) . ?
Fe1 O4 1.956(3) 3_676 ?
Fe1 O5 1.946(3) . ?
Fe1 O6 2.030(3) 4_576 ?
Fe1 O9 2.092(3) . ?
Fe1 O10 2.124(3) 3_666 ?
P1 O1 1.515(3) . ?
P1 O2 1.514(3) . ?
P1 O3 1.572(3) . ?
P1 O4 1.532(3) . ?
P2 O5 1.497(3) . ?
P2 O6 1.507(3) . ?
P2 O7 1.537(4) . ?
P2 O8 1.564(4) . ?
O3 H3 0.8200 . ?
O4 Fe1 1.956(3) 3_676 ?
O6 Fe1 2.030(3) 4_575 ?
O7 H7 0.8200 . ?
O8 H8 0.8200 . ?
O9 C1 1.244(6) . ?
O10 Fe1 2.124(3) 3_666 ?
O10 C1 1.251(5) . ?
C1 C1 1.542(9) 3_666 ?
N1 H1 0.8600 . ?
N1 C3 1.308(9) . ?
N1 C4 1.353(10) . ?
N2 C2 1.472(8) . ?
N2 C3 1.305(8) . ?
N2 C5 1.367(8) . ?
C2 H2A 0.9600 . ?
C2 H2B 0.9600 . ?
C2 H2C 0.9600 . ?
C3 H3A 0.9300 . ?
C4 H4 0.9300 . ?
C4 C5 1.330(9) . ?
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
O1 Fe1 O4 99.85(15) . 3_676 ?
O1 Fe1 O5 94.36(15) . . ?
O1 Fe1 O6 85.89(13) . 4_576 ?
O1 Fe1 O9 165.82(13) . . ?
O1 Fe1 O10 88.82(14) . 3_666 ?
O4 Fe1 O6 85.91(13) 3_676 4_576 ?
O4 Fe1 O9 92.84(13) 3_676 . ?
O4 Fe1 O10 168.60(13) 3_676 3_666 ?
O5 Fe1 O4 96.05(15) . 3_676 ?
O5 Fe1 O6 177.95(14) . 4_576 ?
O5 Fe1 O9 90.52(14) . . ?
O5 Fe1 O10 90.61(14) . 3_666 ?
O6 Fe1 O9 88.77(13) 4_576 . ?
O6 Fe1 O10 87.36(13) 4_576 3_666 ?
O9 Fe1 O10 77.80(13) . 3_666 ?
O1 P1 O3 109.1(2) . . ?
O1 P1 O4 109.64(18) . . ?
O2 P1 O1 110.26(19) . . ?
O2 P1 O3 108.44(18) . . ?
O2 P1 O4 113.04(19) . . ?
O4 P1 O3 106.20(18) . . ?
O5 P2 O6 112.0(2) . . ?
O5 P2 O7 111.7(2) . . ?
O5 P2 O8 110.5(2) . . ?
O6 P2 O7 110.2(2) . . ?
O6 P2 O8 104.1(2) . . ?
O7 P2 O8 107.9(3) . . ?
P1 O1 Fe1 149.4(2) . . ?
P1 O3 H3 109.5 . . ?
P1 O4 Fe1 135.92(19) . 3_676 ?
P2 O5 Fe1 164.3(3) . . ?
P2 O6 Fe1 143.1(2) . 4_575 ?
P2 O7 H7 109.5 . . ?
P2 O8 H8 109.5 . . ?
C1 O9 Fe1 115.2(3) . . ?
C1 O10 Fe1 114.4(3) . 3_666 ?
O9 C1 O10 127.4(4) . . ?
O9 C1 C1 116.8(5) . 3_666 ?
O10 C1 C1 115.8(5) . 3_666 ?
C3 N1 H1 125.4 . . ?
C3 N1 C4 109.2(5) . . ?
C4 N1 H1 125.4 . . ?
C3 N2 C2 126.0(6) . . ?
C3 N2 C5 108.4(5) . . ?
C5 N2 C2 125.6(6) . . ?
N2 C2 H2A 109.5 . . ?
N2 C2 H2B 109.5 . . ?
N2 C2 H2C 109.5 . . ?
H2A C2 H2B 109.5 . . ?
H2A C2 H2C 109.5 . . ?
H2B C2 H2C 109.5 . . ?
N1 C3 H3A 125.7 . . ?
N2 C3 N1 108.6(6) . . ?
N2 C3 H3A 125.7 . . ?
N1 C4 H4 126.6 . . ?
C5 C4 N1 106.8(6) . . ?
C5 C4 H4 126.6 . . ?
N2 C5 H5 126.5 . . ?
C4 C5 N2 107.0(6) . . ?
C4 C5 H5 126.5 . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O3 H3 O2 0.82 1.88 2.688(4) 167.5 3_576
O7 H7 O2 0.82 1.71 2.486(5) 156.1 3_676
O8 H8 O4 0.82 2.16 2.936(5) 157.6 .
N1 H1 O6 0.86 2.00 2.854(6) 170.2 .

