# Electronic Supplementary Material (ESI) for New Journal of Chemistry.
# This journal is © The Royal Society of Chemistry and the Centre National de la Recherche Scientifique 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_LH2-erm38
_database_code_depnum_ccdc_archive 'CCDC 2103571'
loop_
_audit_author_name
_audit_author_address
'Marcos Flores-Alamo'
;Facultad de Quimica Universidad Nacional Autonoma de Mexico
Mexico
;
_audit_update_record             
;
2021-08-16 deposited with the CCDC.	2022-02-28 downloaded from the CCDC.
;

_audit_creation_date             2021-06-30T14:08:09-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.5
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C12 H10 N2 O4 S'
_chemical_formula_weight         278.28

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.4648(8)
_cell_length_b                   10.4074(17)
_cell_length_c                   10.6121(19)
_cell_angle_alpha                82.244(14)
_cell_angle_beta                 81.501(14)
_cell_angle_gamma                78.883(13)
_cell_volume                     582.19(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    1643
_cell_measurement_theta_min      3.83
_cell_measurement_theta_max      29.539

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.31
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_exptl_crystal_density_diffrn    1.587
_exptl_crystal_F_000             288
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
0 -2 14 0.0247
0 2 -14 0.0247
1 14 4 0.0742
-1 -14 -4 0.0742
6 11 5 0.0956
-6 -11 -5 0.0956
7 -2 1 0.1515
-7 2 -1 0.1515


#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.29
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
        (compiled Aug  2 2013,16:46:58)
Analytical numeric absorption correction using a multifaceted crystal
                        model based on expressions derived by R.C. Clark & J.S.
        (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_absorpt_correction_T_min  0.947
_exptl_absorpt_correction_T_max  0.986
_shelx_estimated_absorpt_T_min   0.915
_shelx_estimated_absorpt_T_max   0.986

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_detector_area_resol_mean 10.4685
_diffrn_orient_matrix_ub_11      0.0854276
_diffrn_orient_matrix_ub_12      -0.0401212
_diffrn_orient_matrix_ub_13      -0.0418476
_diffrn_orient_matrix_ub_21      -0.032884
_diffrn_orient_matrix_ub_22      0.0460067
_diffrn_orient_matrix_ub_23      -0.0531083
_diffrn_orient_matrix_ub_31      0.0969352
_diffrn_orient_matrix_ub_32      0.0340105
_diffrn_orient_matrix_ub_33      0.0071503
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0581
_diffrn_reflns_av_unetI/netI     0.0698
_diffrn_reflns_number            6519
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.83
_diffrn_reflns_theta_max         29.539
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.846
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.846
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.846
_reflns_Friedel_coverage         0
_reflns_number_total             2763
_reflns_number_gt                2011
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
        (compiled Aug  2 2013,16:46:58)
;
_computing_cell_refinement       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
        (compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
        (compiled Aug  2 2013,16:46:58)
;
_computing_structure_solution    
;
      'SHELXS-2018 (Sheldrick, 2015)'
      Sheldrick, G. M. (2015). Acta Cryst. A71, 3--8.
;
_computing_structure_refinement  
;
      'SHELXS-2018 (Sheldrick, 2015)'
      Sheldrick, G. M. (2015). Acta Cryst. C71, 3--8.
;
_computing_molecular_graphics    
;
          'Ortep-3 for Windows (Farrugia, 1997)'
      L. J. Farrugia, J. Appl. Crystallogr., 1997, 30, 565.
;
_computing_publication_material  
;	
        'WinGX publication routines (Farrugia, 1999)'				 
	L. J. Farrugia, J. Appl. Crystallogr., 1999, 32, 837-838.
;


#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0495P)²+0.2480P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2763
_refine_ls_number_parameters     174
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0852
_refine_ls_R_factor_gt           0.0532
_refine_ls_wR_factor_ref         0.1269
_refine_ls_wR_factor_gt          0.1107
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_restrained_S_all      1.017
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.393
_refine_diff_density_min         -0.33
_refine_diff_density_rms         0.076

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
S1 S 0.75778(11) 0.69334(7) 0.93396(6) 0.0274(2) Uani 1 1 d . . . . .
O1 O 0.0886(3) 0.57871(16) 0.63209(15) 0.0202(4) Uani 1 1 d . . . . .
H1 H -0.012296 0.532719 0.617305 0.03 Uiso 1 1 calc R U . . .
O2 O 0.2113(3) 0.57368(16) 0.42264(15) 0.0192(4) Uani 1 1 d . . . . .
O3 O 0.8886(3) 0.78801(17) 0.21725(15) 0.0214(4) Uani 1 1 d . . . . .
H3 H 1.018729 0.789614 0.164302 0.032 Uiso 1 1 calc R U . . .
O4 O 1.0560(3) 0.92093(17) 0.31497(16) 0.0218(4) Uani 1 1 d . . . . .
N1 N 0.5464(4) 0.9163(2) 0.75499(18) 0.0217(5) Uani 1 1 d . . . . .
H1A H 0.657423 0.967991 0.751929 0.026 Uiso 1 1 calc R U . . .
N2 N 0.3220(4) 0.7381(2) 1.05986(18) 0.0210(5) Uani 1 1 d . . . . .
C1 C 0.3939(4) 0.7061(2) 0.5334(2) 0.0145(5) Uani 1 1 d . . . . .
C2 C 0.3876(4) 0.7637(2) 0.6456(2) 0.0150(5) Uani 1 1 d . . . . .
H2 H 0.274935 0.742691 0.719321 0.018 Uiso 1 1 calc R U . . .
C3 C 0.5478(4) 0.8524(2) 0.6487(2) 0.0153(5) Uani 1 1 d . . . . .
C4 C 0.7149(4) 0.8792(2) 0.5394(2) 0.0154(5) Uani 1 1 d . . . . .
H4 H 0.825849 0.938887 0.540509 0.018 Uiso 1 1 calc R U . . .
C5 C 0.7208(4) 0.8201(2) 0.4296(2) 0.0144(5) Uani 1 1 d . . . . .
C6 C 0.5586(4) 0.7337(2) 0.4257(2) 0.0140(5) Uani 1 1 d . . . . .
H6 H 0.560772 0.694008 0.349941 0.017 Uiso 1 1 calc R U . . .
C7 C 0.2236(4) 0.6139(2) 0.5245(2) 0.0154(5) Uani 1 1 d . . . . .
C8 C 0.9054(4) 0.8492(2) 0.3165(2) 0.0149(5) Uani 1 1 d . . . . .
C9 C 0.4554(5) 0.6279(2) 1.1232(2) 0.0240(6) Uani 1 1 d . . . . .
H9 H 0.384184 0.582226 1.199209 0.029 Uiso 1 1 calc R U . . .
C10 C 0.6921(5) 0.5902(3) 1.0699(2) 0.0290(6) Uani 1 1 d . . . . .
H10 H 0.806737 0.517059 1.102689 0.035 Uiso 1 1 calc R U . . .
C11 C 0.4587(4) 0.7825(2) 0.9585(2) 0.0181(5) Uani 1 1 d . . . . .
C12 C 0.3751(4) 0.9031(2) 0.8694(2) 0.0191(5) Uani 1 1 d . . . . .
H12A H 0.208199 0.898786 0.846185 0.023 Uiso 1 1 calc R U . . .
H12B H 0.35683 0.982156 0.914763 0.023 Uiso 1 1 calc R U . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C10 1.715(3) . ?
S1 C11 1.719(2) . ?
O1 C7 1.313(3) . ?
O1 H1 0.84 . ?
O2 C7 1.225(3) . ?
O3 C8 1.325(3) . ?
O3 H3 0.84 . ?
O4 C8 1.210(3) . ?
N1 C3 1.383(3) . ?
N1 C12 1.428(3) . ?
N1 H1A 0.88 . ?
N2 C11 1.300(3) . ?
N2 C9 1.383(3) . ?
C1 C6 1.380(3) . ?
C1 C2 1.397(3) . ?
C1 C7 1.481(3) . ?
C2 C3 1.396(3) . ?
C2 H2 0.95 . ?
C3 C4 1.399(3) . ?
C4 C5 1.382(3) . ?
C4 H4 0.95 . ?
C5 C6 1.387(3) . ?
C5 C8 1.488(3) . ?
C6 H6 0.95 . ?
C9 C10 1.340(4) . ?
C9 H9 0.95 . ?
C10 H10 0.95 . ?
C11 C12 1.504(3) . ?
C12 H12A 0.99 . ?
C12 H12B 0.99 . ?

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
C10 S1 C11 89.58(12) . . ?
C7 O1 H1 109.5 . . ?
C8 O3 H3 109.5 . . ?
C3 N1 C12 123.74(19) . . ?
C3 N1 H1A 118.1 . . ?
C12 N1 H1A 118.1 . . ?
C11 N2 C9 110.9(2) . . ?
C6 C1 C2 121.2(2) . . ?
C6 C1 C7 117.19(19) . . ?
C2 C1 C7 121.57(19) . . ?
C3 C2 C1 119.6(2) . . ?
C3 C2 H2 120.2 . . ?
C1 C2 H2 120.2 . . ?
N1 C3 C2 122.8(2) . . ?
N1 C3 C4 118.5(2) . . ?
C2 C3 C4 118.8(2) . . ?
C5 C4 C3 120.9(2) . . ?
C5 C4 H4 119.6 . . ?
C3 C4 H4 119.6 . . ?
C4 C5 C6 120.4(2) . . ?
C4 C5 C8 119.1(2) . . ?
C6 C5 C8 120.5(2) . . ?
C1 C6 C5 119.1(2) . . ?
C1 C6 H6 120.4 . . ?
C5 C6 H6 120.4 . . ?
O2 C7 O1 122.8(2) . . ?
O2 C7 C1 121.5(2) . . ?
O1 C7 C1 115.65(19) . . ?
O4 C8 O3 123.3(2) . . ?
O4 C8 C5 123.7(2) . . ?
O3 C8 C5 112.95(18) . . ?
C10 C9 N2 115.3(2) . . ?
C10 C9 H9 122.4 . . ?
N2 C9 H9 122.4 . . ?
C9 C10 S1 110.1(2) . . ?
C9 C10 H10 125 . . ?
S1 C10 H10 125 . . ?
N2 C11 C12 125.0(2) . . ?
N2 C11 S1 114.15(18) . . ?
C12 C11 S1 120.79(17) . . ?
N1 C12 C11 112.9(2) . . ?
N1 C12 H12A 109 . . ?
C11 C12 H12A 109 . . ?
N1 C12 H12B 109 . . ?
C11 C12 H12B 109 . . ?
H12A C12 H12B 107.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 C1 C2 C3 1.0(3) . . . . ?
C7 C1 C2 C3 -178.58(19) . . . . ?
C12 N1 C3 C2 -2.9(3) . . . . ?
C12 N1 C3 C4 176.2(2) . . . . ?
C1 C2 C3 N1 177.9(2) . . . . ?
C1 C2 C3 C4 -1.3(3) . . . . ?
N1 C3 C4 C5 -178.7(2) . . . . ?
C2 C3 C4 C5 0.5(3) . . . . ?
C3 C4 C5 C6 0.6(3) . . . . ?
C3 C4 C5 C8 -178.7(2) . . . . ?
C2 C1 C6 C5 0.1(3) . . . . ?
C7 C1 C6 C5 179.71(19) . . . . ?
C4 C5 C6 C1 -0.9(3) . . . . ?
C8 C5 C6 C1 178.35(19) . . . . ?
C6 C1 C7 O2 -7.0(3) . . . . ?
C2 C1 C7 O2 172.5(2) . . . . ?
C6 C1 C7 O1 172.98(19) . . . . ?
C2 C1 C7 O1 -7.5(3) . . . . ?
C4 C5 C8 O4 1.2(3) . . . . ?
C6 C5 C8 O4 -178.1(2) . . . . ?
C4 C5 C8 O3 -178.97(19) . . . . ?
C6 C5 C8 O3 1.7(3) . . . . ?
C11 N2 C9 C10 0.4(3) . . . . ?
N2 C9 C10 S1 -0.5(3) . . . . ?
C11 S1 C10 C9 0.4(2) . . . . ?
C9 N2 C11 C12 -178.3(2) . . . . ?
C9 N2 C11 S1 -0.1(3) . . . . ?
C10 S1 C11 N2 -0.17(19) . . . . ?
C10 S1 C11 C12 178.1(2) . . . . ?
C3 N1 C12 C11 83.1(3) . . . . ?
N2 C11 C12 N1 -170.1(2) . . . . ?
S1 C11 C12 N1 11.8(3) . . . . ?

####################################################################### 
# 
# 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_erm032r
_database_code_depnum_ccdc_archive 'CCDC 2103572'
loop_
_audit_author_name
_audit_author_address
'Marcos Flores-Alamo'
;Facultad de Quimica Universidad Nacional Autonoma de Mexico
Mexico
;
_audit_update_record             
;
2021-08-24 deposited with the CCDC.	2022-02-28 downloaded from the CCDC.
;

_audit_creation_date             2021-08-24T11:53:54-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.5
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C8 H9 Fe N O6'
_chemical_formula_moiety         'C8 H7 Fe N O5, H2 O'
_chemical_formula_weight         271.01

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           triclinic
_symmetry_space_group_name_H-M   'P -1'
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   7.394(3)
_cell_length_b                   8.345(3)
_cell_length_c                   8.843(4)
_cell_angle_alpha                62.78(4)
_cell_angle_beta                 71.92(3)
_cell_angle_gamma                80.61(3)
_cell_volume                     461.1(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    119(2)
_cell_measurement_reflns_used    1804
_cell_measurement_theta_min      3.3843
_cell_measurement_theta_max      29.4127

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.456
_exptl_crystal_size_mid          0.181
_exptl_crystal_size_min          0.154
_exptl_crystal_density_diffrn    1.952
_exptl_crystal_F_000             276
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
-6 -6 3 0.0903
6 6 -3 0.0903
-7 6 3 0.2064
7 -6 -3 0.2064
-2 10 0 0.2211
2 -10 0 0.2211
-6 -6 -12 0.0769
6 6 12 0.0769
1 10 10 0.1221


#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    1.649
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
        (compiled Aug  2 2013,16:46:58)
        Analytical numeric absorption correction using a multifaceted crystal
                        model based on expressions derived by R.C. Clark & J.S.
        (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_absorpt_correction_T_min  0.617
_exptl_absorpt_correction_T_max  0.799
_shelx_estimated_absorpt_T_min   0.52
_shelx_estimated_absorpt_T_max   0.785

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      119(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_detector_area_resol_mean 10.4685
_diffrn_orient_matrix_ub_11      0.0485093
_diffrn_orient_matrix_ub_12      0.0184834
_diffrn_orient_matrix_ub_13      0.0474295
_diffrn_orient_matrix_ub_21      0.0667103
_diffrn_orient_matrix_ub_22      0.0509639
_diffrn_orient_matrix_ub_23      -0.0800994
_diffrn_orient_matrix_ub_31      -0.0584455
_diffrn_orient_matrix_ub_32      0.0785196
_diffrn_orient_matrix_ub_33      -0.0086357
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.0257
_diffrn_reflns_av_unetI/netI     0.0419
_diffrn_reflns_number            5074
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         3.384
_diffrn_reflns_theta_max         29.439
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.856
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.856
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.856
_reflns_Friedel_coverage         0
_reflns_number_total             2189
_reflns_number_gt                1951
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
        (compiled Aug  2 2013,16:46:58)
;
_computing_cell_refinement       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
        (compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
        (compiled Aug  2 2013,16:46:58)
;
_computing_structure_solution    
;
      'SHELXS-2018 (Sheldrick, 2015)'
      Sheldrick, G. M. (2015). Acta Cryst. A71, 3--8.
;
_computing_structure_refinement  
;
      'SHELXS-2018 (Sheldrick, 2015)'
      Sheldrick, G. M. (2015). Acta Cryst. C71, 3--8.
;
_computing_molecular_graphics    
;
          'Ortep-3 for Windows (Farrugia, 1997)'
      L. J. Farrugia, J. Appl. Crystallogr., 1997, 30, 565.
;
_computing_publication_material  
;	
        'WinGX publication routines (Farrugia, 1999)'				 
	L. J. Farrugia, J. Appl. Crystallogr., 1999, 32, 837-838.
;



#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   mixed

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0328P)²+0.4863P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2189
_refine_ls_number_parameters     163
_refine_ls_number_restraints     5
_refine_ls_R_factor_all          0.0412
_refine_ls_R_factor_gt           0.0337
_refine_ls_wR_factor_ref         0.0816
_refine_ls_wR_factor_gt          0.0756
_refine_ls_goodness_of_fit_ref   1.082
_refine_ls_restrained_S_all      1.087
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.933
_refine_diff_density_min         -0.776
_refine_diff_density_rms         0.093

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Fe Fe 0.3463 0.8444 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.7235(3) 0.6185(3) 0.3382(3) 0.0087(4) Uani 1 1 d . . . . .
C2 C 0.5990(3) 0.7624(3) 0.2756(3) 0.0088(4) Uani 1 1 d . . . . .
H2 H 0.592766 0.811295 0.156941 0.011 Uiso 1 1 calc R U . . .
C3 C 0.4844(3) 0.8332(3) 0.3891(3) 0.0092(4) Uani 1 1 d . . . . .
C4 C 0.4926(3) 0.7618(3) 0.5622(3) 0.0093(4) Uani 1 1 d . . . . .
H4 H 0.409811 0.808028 0.640028 0.011 Uiso 1 1 calc R U . . .
C5 C 0.6218(3) 0.6221(3) 0.6227(3) 0.0087(4) Uani 1 1 d . . . . .
C6 C 0.7386(3) 0.5520(3) 0.5095(3) 0.0092(4) Uani 1 1 d . . . . .
H6 H 0.829041 0.458605 0.549053 0.011 Uiso 1 1 calc R U . . .
C7 C 0.8344(3) 0.5272(3) 0.2247(3) 0.0102(4) Uani 1 1 d . . . . .
C8 C 0.3549(3) 0.9917(3) 0.3233(3) 0.0098(4) Uani 1 1 d . . . . .
Fe1 Fe 1.16514(5) 0.27638(4) 0.18020(4) 0.00942(11) Uani 1 1 d . . . . .
N1 N 0.6338(3) 0.5549(3) 0.7991(3) 0.0105(4) Uani 1 1 d D . . . .
O1 O 0.9598(2) 0.4128(2) 0.2836(2) 0.0131(4) Uani 1 1 d . . . . .
O2 O 0.7922(2) 0.5625(2) 0.0856(2) 0.0126(4) Uani 1 1 d . . . . .
O1W O 0.9782(2) 0.0840(2) 0.2041(2) 0.0152(4) Uani 1 1 d D . . . .
O3 O 0.3923(2) 1.0907(2) 0.1571(2) 0.0115(3) Uani 1 1 d . . . . .
O2W O 0.7757(3) 1.1631(2) -0.0402(2) 0.0173(4) Uani 1 1 d D . . . .
O4 O 0.2180(2) 1.0311(2) 0.4262(2) 0.0111(3) Uani 1 1 d . . . . .
H1G H 0.685(4) 0.444(4) 0.840(4) 0.013 Uiso 1 1 d . U . . .
H1D H 0.916(4) 0.116(4) 0.132(3) 0.017 Uiso 1 1 d D U . . .
H1E H 0.919(4) 0.033(4) 0.312(2) 0.017 Uiso 1 1 d D U . . .
H2E H 0.824(4) 1.097(4) -0.092(4) 0.017 Uiso 1 1 d D U . . .
H2D H 0.663(3) 1.126(4) 0.017(4) 0.017 Uiso 1 1 d D U . . .
H1F H 0.706(3) 0.633(3) 0.776(4) 0.013 Uiso 1 1 d D U . . .



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
C1 C6 1.389(3) . ?
C1 C2 1.393(3) . ?
C1 C7 1.499(3) . ?
C2 C3 1.388(3) . ?
C2 H2 0.95 . ?
C3 C4 1.383(3) . ?
C3 C8 1.494(3) . ?
C4 C5 1.393(3) . ?
C4 H4 0.95 . ?
C5 C6 1.387(3) . ?
C5 N1 1.423(3) . ?
C6 H6 0.95 . ?
C7 O2 1.254(3) . ?
C7 O1 1.264(3) . ?
C8 O4 1.247(3) . ?
C8 O3 1.277(3) . ?
Fe1 O1 1.9914(18) . ?
Fe1 O2 2.054(2) 2_765 ?
Fe1 O3 2.1191(18) 1_645 ?
Fe1 O1W 2.183(2) . ?
Fe1 O4 2.295(2) 1_645 ?
Fe1 N1 2.305(2) 2_766 ?
N1 H1G 0.89(3) . ?
N1 H1F 0.824(17) . ?
O1W H1D 0.823(17) . ?
O1W H1E 0.846(17) . ?
O2W H2E 0.841(18) . ?
O2W H2D 0.851(17) . ?

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
C6 C1 C2 120.5(2) . . ?
C6 C1 C7 119.2(2) . . ?
C2 C1 C7 120.2(2) . . ?
C3 C2 C1 119.1(2) . . ?
C3 C2 H2 120.5 . . ?
C1 C2 H2 120.5 . . ?
C4 C3 C2 120.6(2) . . ?
C4 C3 C8 119.4(2) . . ?
C2 C3 C8 120.0(2) . . ?
C3 C4 C5 120.2(2) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
C6 C5 C4 119.5(2) . . ?
C6 C5 N1 120.9(2) . . ?
C4 C5 N1 119.6(2) . . ?
C5 C6 C1 120.0(2) . . ?
C5 C6 H6 120 . . ?
C1 C6 H6 120 . . ?
O2 C7 O1 125.3(2) . . ?
O2 C7 C1 118.9(2) . . ?
O1 C7 C1 115.7(2) . . ?
O4 C8 O3 120.3(2) . . ?
O4 C8 C3 121.7(2) . . ?
O3 C8 C3 117.9(2) . . ?
O1 Fe1 O2 101.82(8) . 2_765 ?
O1 Fe1 O3 160.89(7) . 1_645 ?
O2 Fe1 O3 96.44(8) 2_765 1_645 ?
O1 Fe1 O1W 95.92(8) . . ?
O2 Fe1 O1W 97.57(8) 2_765 . ?
O3 Fe1 O1W 87.15(7) 1_645 . ?
O1 Fe1 O4 102.54(7) . 1_645 ?
O2 Fe1 O4 155.64(6) 2_765 1_645 ?
O3 Fe1 O4 59.31(7) 1_645 1_645 ?
O1W Fe1 O4 80.08(7) . 1_645 ?
O1 Fe1 N1 84.25(8) . 2_766 ?
O2 Fe1 N1 91.67(8) 2_765 2_766 ?
O3 Fe1 N1 89.67(7) 1_645 2_766 ?
O1W Fe1 N1 170.50(7) . 2_766 ?
O4 Fe1 N1 90.60(8) 1_645 2_766 ?
C5 N1 Fe1 111.33(15) . 2_766 ?
C5 N1 H1G 113.7(18) . . ?
Fe1 N1 H1G 102.9(18) 2_766 . ?
C5 N1 H1F 95(2) . . ?
Fe1 N1 H1F 17(2) 2_766 . ?
H1G N1 H1F 112(3) . . ?
C7 O1 Fe1 133.08(16) . . ?
C7 O2 Fe1 147.37(17) . 2_765 ?
Fe1 O1W H1D 119(2) . . ?
Fe1 O1W H1E 107(2) . . ?
H1D O1W H1E 117(3) . . ?
C8 O3 Fe1 93.78(13) . 1_465 ?
H2E O2W H2D 105(3) . . ?
C8 O4 Fe1 86.56(14) . 1_465 ?

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
C6 C1 C2 C3 -2.8(3) . . . . ?
C7 C1 C2 C3 173.8(2) . . . . ?
C1 C2 C3 C4 -0.3(3) . . . . ?
C1 C2 C3 C8 177.8(2) . . . . ?
C2 C3 C4 C5 2.6(3) . . . . ?
C8 C3 C4 C5 -175.6(2) . . . . ?
C3 C4 C5 C6 -1.7(3) . . . . ?
C3 C4 C5 N1 177.5(2) . . . . ?
C4 C5 C6 C1 -1.4(3) . . . . ?
N1 C5 C6 C1 179.4(2) . . . . ?
C2 C1 C6 C5 3.7(3) . . . . ?
C7 C1 C6 C5 -173.0(2) . . . . ?
C6 C1 C7 O2 165.6(2) . . . . ?
C2 C1 C7 O2 -11.1(3) . . . . ?
C6 C1 C7 O1 -11.4(3) . . . . ?
C2 C1 C7 O1 171.9(2) . . . . ?
C4 C3 C8 O4 -20.2(3) . . . . ?
C2 C3 C8 O4 161.6(2) . . . . ?
C4 C3 C8 O3 157.4(2) . . . . ?
C2 C3 C8 O3 -20.8(3) . . . . ?
C6 C5 N1 Fe1 93.9(2) . . . 2_766 ?
C4 C5 N1 Fe1 -85.3(2) . . . 2_766 ?
O2 C7 O1 Fe1 11.9(4) . . . . ?
C1 C7 O1 Fe1 -171.35(15) . . . . ?
O1 C7 O2 Fe1 -93.9(3) . . . 2_765 ?
C1 C7 O2 Fe1 89.4(3) . . . 2_765 ?
O4 C8 O3 Fe1 0.5(2) . . . 1_465 ?
C3 C8 O3 Fe1 -177.13(18) . . . 1_465 ?
O3 C8 O4 Fe1 -0.5(2) . . . 1_465 ?
C3 C8 O4 Fe1 177.1(2) . . . 1_465 ?

####################################################################### 
# 
# 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_5-erm41d-1342_tw
_database_code_depnum_ccdc_archive 'CCDC 2103573'
loop_
_audit_author_name
_audit_author_address
'Marcos Flores-Alamo'
;Facultad de Quimica Universidad Nacional Autonoma de Mexico
Mexico
;
_audit_update_record             
;
2021-08-16 deposited with the CCDC.	2022-02-28 downloaded from the CCDC.
;

_audit_creation_date             2021-06-30T13:15:02-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.5
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_formula_sum            'C12 H8 Mn N2 O4 S'
_chemical_formula_weight         331.2

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/c'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'

_cell_length_a                   8.7610(10)
_cell_length_b                   10.3491(14)
_cell_length_c                   14.860(2)
_cell_angle_alpha                90
_cell_angle_beta                 91.067(13)
_cell_angle_gamma                90
_cell_volume                     1347.1(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    120(2)
_cell_measurement_reflns_used    3054
_cell_measurement_theta_min      3.903
_cell_measurement_theta_max      27.09

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_size_max          0.225
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.083
_exptl_crystal_density_diffrn    1.633
_exptl_crystal_F_000             668
loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
1 14 -5 0.0546
0 -4 -20 0.0418
0 4 20 0.0418
12 -3 -2 0.0992
-12 3 2 0.0992
-1 -14 5 0.0546


#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    1.147
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
        (compiled Aug  2 2013,16:46:58)
Analytical numeric absorption correction using a multifaceted crystal
                        model based on expressions derived by R.C. Clark & J.S.
        (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
;
_exptl_absorpt_correction_T_min  0.851
_exptl_absorpt_correction_T_max  0.915
_shelx_estimated_absorpt_T_min   0.782
_shelx_estimated_absorpt_T_max   0.911

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_ambient_temperature      120(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_detector_area_resol_mean 10.4685
_diffrn_orient_matrix_ub_11      0.0150565
_diffrn_orient_matrix_ub_12      0.0466876
_diffrn_orient_matrix_ub_13      -0.0339139
_diffrn_orient_matrix_ub_21      -0.0204934
_diffrn_orient_matrix_ub_22      -0.0453448
_diffrn_orient_matrix_ub_23      -0.0333567
_diffrn_orient_matrix_ub_31      -0.0767819
_diffrn_orient_matrix_ub_32      0.0212615
_diffrn_orient_matrix_ub_33      0.0032795
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini'
_diffrn_measurement_method       'ω scans'
_diffrn_reflns_av_R_equivalents  0.1103
_diffrn_reflns_av_unetI/netI     0.1284
_diffrn_reflns_number            2388
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         3.323
_diffrn_reflns_theta_max         25.026
_diffrn_reflns_theta_full        25.026
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_reflns_Friedel_coverage         0
_reflns_number_total             2388
_reflns_number_gt                1987
_reflns_threshold_expression     'I > 2σ(I)'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
        (compiled Aug  2 2013,16:46:58)
;
_computing_cell_refinement       
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
        (compiled Aug  2 2013,16:46:58)
;
_computing_data_reduction        
;
        CrysAlisPro, Agilent Technologies,
        Version 1.171.36.32 (release 02-08-2013 CrysAlis171 .NET)
        (compiled Aug  2 2013,16:46:58)
;
_computing_structure_solution    
;
      'SHELXS-2018 (Sheldrick, 2015)'
      Sheldrick, G. M. (2015). Acta Cryst. A71, 3--8.
;
_computing_structure_refinement  
;
      'SHELXS-2018 (Sheldrick, 2015)'
      Sheldrick, G. M. (2015). Acta Cryst. C71, 3--8.
;
_computing_molecular_graphics    
;
          'Ortep-3 for Windows (Farrugia, 1997)'
      L. J. Farrugia, J. Appl. Crystallogr., 1997, 30, 565.
;
_computing_publication_material  
;	
        'WinGX publication routines (Farrugia, 1999)'				 
	L. J. Farrugia, J. Appl. Crystallogr., 1999, 32, 837-838.
;


#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_hydrogens   geom

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
 Refined as a 2-component twin.

C9, C9 and C9A, C10A are disordered over two sites with 
occupancies of 0.60:40

;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0714P)²+24.9127P] where P=(Fo²+2Fc²)/3'
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_number_reflns         2388
_refine_ls_number_parameters     177
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.1082
_refine_ls_R_factor_gt           0.0953
_refine_ls_wR_factor_ref         0.2668
_refine_ls_wR_factor_gt          0.2591
_refine_ls_goodness_of_fit_ref   1.116
_refine_ls_restrained_S_all      1.116
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_diff_density_max         1.581
_refine_diff_density_min         -1.431
_refine_diff_density_rms         0.202

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Mn Mn 0.3368 0.7283 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

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 0.61564(15) 0.38891(13) 0.50917(9) 0.0167(4) Uani 1 1 d . . . . .
S1 S 0.7985(6) -0.0180(4) 0.4315(3) 0.0618(12) Uani 1 1 d . . . . .
O1 O 0.7733(9) 0.4893(7) 0.5984(5) 0.0252(16) Uani 1 1 d . . . . .
O2 O 0.4132(9) 0.3721(7) 0.4251(5) 0.0293(18) Uani 1 1 d . . . . .
O3 O 0.4752(8) 0.3513(7) 0.6201(5) 0.0264(17) Uani 1 1 d . . . . .
O4 O 0.7064(8) 0.5001(7) 0.4049(4) 0.0246(16) Uani 1 1 d . . . . .
N1 N 1.1509(11) 0.8480(10) 0.7342(6) 0.035(2) Uani 1 1 d . . . . .
H1 H 1.180799 0.906217 0.773923 0.042 Uiso 1 1 calc R U . . .
N2 N 0.7068(10) 0.1968(8) 0.4935(6) 0.029(2) Uani 1 1 d D . . . .
C1 C 0.7828(12) 0.6899(10) 0.6766(6) 0.021(2) Uani 1 1 d . . . . .
C2 C 0.9349(12) 0.7183(11) 0.6741(7) 0.024(2) Uani 1 1 d . . . . .
H2 H 0.997348 0.674834 0.632239 0.029 Uiso 1 1 calc R U . . .
C3 C 1.0011(13) 0.8111(11) 0.7327(7) 0.0305(19) Uani 1 1 d . . . . .
C4 C 0.9035(12) 0.8684(11) 0.7957(7) 0.025(2) Uani 1 1 d . . . . .
H4 H 0.943571 0.92969 0.837427 0.03 Uiso 1 1 calc R U . . .
C5 C 0.7511(11) 0.8367(10) 0.7977(6) 0.021(2) Uani 1 1 d . . . . .
C6 C 0.6881(10) 0.7501(11) 0.7383(6) 0.020(2) Uani 1 1 d . . . . .
H6 H 0.581998 0.731359 0.738914 0.024 Uiso 1 1 calc R U . . .
C7 C 0.7083(13) 0.5956(10) 0.6109(6) 0.024(2) Uani 1 1 d . . . . .
C8 C 0.3473(13) 0.4016(10) 0.6343(6) 0.025(2) Uani 1 1 d . . . . .
C11 C 0.7464(13) 0.1399(12) 0.4180(8) 0.035(3) Uani 1 1 d D . . . .
C12 C 0.7381(12) 0.2038(12) 0.3261(7) 0.029(2) Uani 1 1 d . . . . .
H12A H 0.634592 0.191239 0.299675 0.035 Uiso 1 1 calc R U . . .
H12B H 0.755278 0.297789 0.33319 0.035 Uiso 1 1 calc R U . . .
C9 C 0.695(4) 0.096(3) 0.555(2) 0.0305(19) Uani 0.40(4) 1 d D . P A 1
H9 H 0.659937 0.113065 0.613956 0.037 Uiso 0.40(4) 1 calc R U P A 1
C10 C 0.732(5) -0.022(2) 0.533(2) 0.0305(19) Uani 0.40(4) 1 d D . P A 1
H10 H 0.722585 -0.096248 0.570075 0.037 Uiso 0.40(4) 1 calc R U P A 1
C9A C 0.733(3) 0.120(2) 0.5694(13) 0.0305(19) Uani 0.60(4) 1 d D . P A 2
H9A H 0.718297 0.149868 0.62904 0.037 Uiso 0.60(4) 1 calc R U P A 2
C10A C 0.783(3) -0.0023(19) 0.5499(14) 0.0305(19) Uani 0.60(4) 1 d D . P A 2
H10A H 0.804942 -0.068058 0.59283 0.037 Uiso 0.60(4) 1 calc R U P A 2



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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 O4 2.098(7) . ?
Mn1 O3 2.112(7) . ?
Mn1 N2 2.156(9) . ?
Mn1 O2 2.157(7) . ?
Mn1 O1 2.163(7) . ?
Mn1 Mn1 3.073(3) 3_666 ?
S1 C10 1.63(3) . ?
S1 C11 1.707(13) . ?
S1 C10A 1.78(2) . ?
O1 C7 1.254(13) . ?
O2 C7 1.229(13) 3_666 ?
O3 C8 1.257(13) . ?
O4 C8 1.259(13) 3_666 ?
N1 C3 1.366(15) . ?
N1 C12 1.439(13) 3_766 ?
N1 H1 0.88 . ?
N2 C11 1.319(14) . ?
N2 C9 1.395(19) . ?
N2 C9A 1.395(17) . ?
C1 C2 1.365(15) . ?
C1 C6 1.394(13) . ?
C1 C7 1.520(14) . ?
C2 C3 1.413(15) . ?
C2 H2 0.95 . ?
C3 C4 1.411(16) . ?
C4 C5 1.375(15) . ?
C4 H4 0.95 . ?
C5 C6 1.368(15) . ?
C5 C8 1.499(14) 2_656 ?
C6 H6 0.95 . ?
C11 C12 1.518(16) . ?
C12 H12A 0.99 . ?
C12 H12B 0.99 . ?
C9 C10 1.30(4) . ?
C9 H9 0.95 . ?
C10 H10 0.95 . ?
C9A C10A 1.37(3) . ?
C9A H9A 0.95 . ?
C10A H10A 0.95 . ?

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
O4 Mn1 O3 155.8(3) . . ?
O4 Mn1 N2 106.2(3) . . ?
O3 Mn1 N2 97.9(3) . . ?
O4 Mn1 O2 86.3(3) . . ?
O3 Mn1 O2 87.3(3) . . ?
N2 Mn1 O2 99.5(3) . . ?
O4 Mn1 O1 86.7(3) . . ?
O3 Mn1 O1 89.1(3) . . ?
N2 Mn1 O1 106.0(3) . . ?
O2 Mn1 O1 154.5(3) . . ?
O4 Mn1 Mn1 77.4(2) . 3_666 ?
O3 Mn1 Mn1 79.3(2) . 3_666 ?
N2 Mn1 Mn1 157.7(3) . 3_666 ?
O2 Mn1 Mn1 58.4(2) . 3_666 ?
O1 Mn1 Mn1 96.2(2) . 3_666 ?
C10 S1 C11 91.8(10) . . ?
C11 S1 C10A 90.2(7) . . ?
C7 O1 Mn1 103.0(6) . . ?
C7 O2 Mn1 157.8(7) 3_666 . ?
C8 O3 Mn1 126.0(6) . . ?
C8 O4 Mn1 129.9(7) 3_666 . ?
C3 N1 C12 123.1(9) . 3_766 ?
C3 N1 H1 118.5 . . ?
C12 N1 H1 118.5 3_766 . ?
C11 N2 C9 104.3(17) . . ?
C11 N2 C9A 113.0(13) . . ?
C11 N2 Mn1 127.4(8) . . ?
C9 N2 Mn1 126.1(16) . . ?
C9A N2 Mn1 119.6(11) . . ?
C2 C1 C6 121.0(9) . . ?
C2 C1 C7 121.9(9) . . ?
C6 C1 C7 117.1(9) . . ?
C1 C2 C3 121.3(9) . . ?
C1 C2 H2 119.3 . . ?
C3 C2 H2 119.3 . . ?
N1 C3 C4 117.7(10) . . ?
N1 C3 C2 125.7(10) . . ?
C4 C3 C2 116.5(10) . . ?
C5 C4 C3 121.0(10) . . ?
C5 C4 H4 119.5 . . ?
C3 C4 H4 119.5 . . ?
C6 C5 C4 121.5(9) . . ?
C6 C5 C8 119.9(9) . 2_656 ?
C4 C5 C8 118.6(9) . 2_656 ?
C5 C6 C1 118.6(9) . . ?
C5 C6 H6 120.7 . . ?
C1 C6 H6 120.7 . . ?
O2 C7 O1 124.5(10) 3_666 . ?
O2 C7 C1 117.6(9) 3_666 . ?
O1 C7 C1 117.9(9) . . ?
O3 C8 O4 125.7(10) . 3_666 ?
O3 C8 C5 116.9(9) . 2_646 ?
O4 C8 C5 117.3(10) 3_666 2_646 ?
N2 C11 C12 124.1(10) . . ?
N2 C11 S1 113.7(9) . . ?
C12 C11 S1 122.0(9) . . ?
N1 C12 C11 112.1(10) 3_766 . ?
N1 C12 H12A 109.2 3_766 . ?
C11 C12 H12A 109.2 . . ?
N1 C12 H12B 109.2 3_766 . ?
C11 C12 H12B 109.2 . . ?
H12A C12 H12B 107.9 . . ?
C10 C9 N2 121(3) . . ?
C10 C9 H9 119.5 . . ?
N2 C9 H9 119.5 . . ?
C9 C10 S1 107.7(18) . . ?
C9 C10 H10 126.2 . . ?
S1 C10 H10 126.2 . . ?
C10A C9A N2 113.8(17) . . ?
C10A C9A H9A 123.1 . . ?
N2 C9A H9A 123.1 . . ?
C9A C10A S1 108.9(12) . . ?
C9A C10A H10A 125.5 . . ?
S1 C10A H10A 125.5 . . ?

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
C6 C1 C2 C3 -1.1(16) . . . . ?
C7 C1 C2 C3 176.7(10) . . . . ?
C12 N1 C3 C4 179.6(11) 3_766 . . . ?
C12 N1 C3 C2 0.7(19) 3_766 . . . ?
C1 C2 C3 N1 -178.6(11) . . . . ?
C1 C2 C3 C4 2.5(16) . . . . ?
N1 C3 C4 C5 179.5(11) . . . . ?
C2 C3 C4 C5 -1.6(16) . . . . ?
C3 C4 C5 C6 -0.8(16) . . . . ?
C3 C4 C5 C8 -179.5(10) . . . 2_656 ?
C4 C5 C6 C1 2.3(15) . . . . ?
C8 C5 C6 C1 -179.1(9) 2_656 . . . ?
C2 C1 C6 C5 -1.3(15) . . . . ?
C7 C1 C6 C5 -179.2(9) . . . . ?
Mn1 O1 C7 O2 -2.6(11) . . . 3_666 ?
Mn1 O1 C7 C1 176.0(7) . . . . ?
C2 C1 C7 O2 -134.0(11) . . . 3_666 ?
C6 C1 C7 O2 43.9(13) . . . 3_666 ?
C2 C1 C7 O1 47.4(14) . . . . ?
C6 C1 C7 O1 -134.7(10) . . . . ?
Mn1 O3 C8 O4 -14.4(15) . . . 3_666 ?
Mn1 O3 C8 C5 164.0(6) . . . 2_646 ?
C9 N2 C11 C12 165.4(19) . . . . ?
C9A N2 C11 C12 -176.6(16) . . . . ?
Mn1 N2 C11 C12 1.8(17) . . . . ?
C9 N2 C11 S1 -11(2) . . . . ?
C9A N2 C11 S1 7.0(17) . . . . ?
Mn1 N2 C11 S1 -174.6(6) . . . . ?
C10 S1 C11 N2 12.1(18) . . . . ?
C10A S1 C11 N2 -5.4(13) . . . . ?
C10 S1 C11 C12 -164.4(18) . . . . ?
C10A S1 C11 C12 178.1(14) . . . . ?
N2 C11 C12 N1 151.9(11) . . . 3_766 ?
S1 C11 C12 N1 -32.0(14) . . . 3_766 ?
C11 N2 C9 C10 5(3) . . . . ?
Mn1 N2 C9 C10 169(2) . . . . ?
N2 C9 C10 S1 4(3) . . . . ?
C11 S1 C10 C9 -8(2) . . . . ?
C11 N2 C9A C10A -5(2) . . . . ?
Mn1 N2 C9A C10A 176.4(13) . . . . ?
N2 C9A C10A S1 1(2) . . . . ?
C11 S1 C10A C9A 2.4(15) . . . . ?

