# 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_shelx
_database_code_depnum_ccdc_archive 'CCDC 2133372'
loop_
_audit_author_name
_audit_author_address
'Luan F. Diniz'
;Universidade Federal de Minas Gerais
Brazil
;
_audit_update_record             
;
2022-06-05 deposited with the CCDC.	2022-06-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        'Metformin maleate'
_chemical_formula_moiety         'C4 H3 O4, C4 H12 N5'
_chemical_formula_sum            'C8 H15 N5 O4'
_chemical_formula_weight         245.25
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   10.5887(8)
_cell_length_b                   8.8945(5)
_cell_length_c                   13.6358(9)
_cell_angle_alpha                90
_cell_angle_beta                 107.807(8)
_cell_angle_gamma                90
_cell_volume                     1222.71(15)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2340
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.8590
_cell_measurement_theta_min      2.7850
_shelx_estimated_absorpt_T_max   0.978
_shelx_estimated_absorpt_T_min   0.932
_exptl_absorpt_coefficient_mu    0.108
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83746
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.42a (Rigaku Oxford Diffraction, 2019)
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    1.332
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             520
_exptl_crystal_size_max          0.66
_exptl_crystal_size_mid          0.47
_exptl_crystal_size_min          0.21
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0393
_diffrn_reflns_av_unetI/netI     0.0402
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.987
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            9856
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.987
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.475
_diffrn_reflns_theta_min         2.776
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4186
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -87.00  15.00   1.00    4.50    --  -11.01 -38.00 120.00  102
  2  ω    -80.00  20.00   1.00    4.50    --  -11.01 -77.00  30.00  100
  3  ω    -37.00  54.00   1.00    4.50    --  -11.01  38.00 -60.00   91
  4  ω    -45.00 -15.00   1.00    4.50    --   13.04 135.00  -3.00   30
  5  ω    -13.00  28.00   1.00    4.50    --   13.04  38.00-180.00   41
  6  ω      3.00  28.00   1.00    4.50    --   13.04  77.00 120.00   25
  7  ω    -36.00 -11.00   1.00    4.50    --   13.04 135.00 176.00   25
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0562882000
_diffrn_orient_matrix_UB_12      -0.0065230000
_diffrn_orient_matrix_UB_13      0.0442952000
_diffrn_orient_matrix_UB_21      0.0411477000
_diffrn_orient_matrix_UB_22      -0.0092910000
_diffrn_orient_matrix_UB_23      -0.0319955000
_diffrn_orient_matrix_UB_31      0.0094897000
_diffrn_orient_matrix_UB_32      0.0789125000
_diffrn_orient_matrix_UB_33      -0.0000925000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1858
_reflns_number_total             2759
_reflns_odcompleteness_completeness 99.81
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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 1.171.40.42a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.42a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.42a (Rigaku OD, 2019)'
_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 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.213
_refine_diff_density_min         -0.205
_refine_diff_density_rms         0.040
_refine_ls_extinction_coef       0.082(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         2759
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0769
_refine_ls_R_factor_gt           0.0469
_refine_ls_restrained_S_all      1.028
_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)+(0.0465P)²+0.4228P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1051
_refine_ls_wR_factor_ref         0.1243
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.5 times of:
  All O(H) groups
2.a Idealised tetrahedral OH refined as rotating group:
 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
O2 O 0.65287(13) 0.16583(14) 0.28815(10) 0.0430(4) Uani 1 1 d . . . . .
N4 N 0.60835(16) 0.86518(19) 0.18411(13) 0.0390(4) Uani 1 1 d . . . . .
O3 O 0.55404(18) 0.30038(19) 0.56156(12) 0.0649(5) Uani 1 1 d . . . . .
H3 H 0.560189 0.304231 0.503113 0.097 Uiso 1 1 calc R U . . .
N3 N 0.48813(16) 0.66282(16) 0.09217(11) 0.0377(4) Uani 1 1 d . . . . .
N2 N 0.54865(18) 0.41820(17) 0.13284(14) 0.0430(5) Uani 1 1 d . . . . .
N5 N 0.39665(15) 0.90029(16) 0.07685(12) 0.0377(4) Uani 1 1 d . . . . .
O1 O 0.5780(2) 0.30831(17) 0.39018(12) 0.0720(6) Uani 1 1 d . . . . .
N1 N 0.5358(2) 0.5743(2) 0.26157(13) 0.0478(5) Uani 1 1 d . . . . .
C2 C 0.49644(18) 0.80899(19) 0.12084(12) 0.0315(4) Uani 1 1 d . . . . .
C1 C 0.52503(18) 0.55519(19) 0.16258(13) 0.0338(4) Uani 1 1 d . . . . .
C5 C 0.63201(19) 0.1908(2) 0.37159(14) 0.0363(4) Uani 1 1 d . . . . .
O4 O 0.6047(2) 0.1455(2) 0.69092(14) 0.0925(7) Uani 1 1 d . . . . .
C3 C 0.4051(3) 1.0613(2) 0.0956(2) 0.0496(6) Uani 1 1 d . . . . .
C8 C 0.6059(2) 0.1772(3) 0.60496(17) 0.0519(6) Uani 1 1 d . . . . .
C6 C 0.6780(3) 0.0767(2) 0.45427(17) 0.0540(6) Uani 1 1 d . . . . .
C7 C 0.6690(3) 0.0732(3) 0.54921(19) 0.0622(7) Uani 1 1 d . . . . .
C4 C 0.2657(3) 0.8423(3) 0.0227(3) 0.0754(9) Uani 1 1 d . . . . .
H1A H 0.507(2) 0.660(3) 0.2821(17) 0.052(6) Uiso 1 1 d . . . . .
H1B H 0.547(2) 0.495(3) 0.3017(18) 0.052(6) Uiso 1 1 d . . . . .
H2A H 0.5642(19) 0.344(2) 0.1765(16) 0.039(5) Uiso 1 1 d . . . . .
H2B H 0.535(2) 0.401(2) 0.067(2) 0.055(7) Uiso 1 1 d . . . . .
H4A H 0.676(2) 0.802(2) 0.2065(16) 0.047(6) Uiso 1 1 d . . . . .
H4B H 0.618(2) 0.958(3) 0.2117(16) 0.051(6) Uiso 1 1 d . . . . .
H3A H 0.343(3) 1.111(3) 0.040(2) 0.071(7) Uiso 1 1 d . . . . .
H3B H 0.391(2) 1.079(3) 0.160(2) 0.057(7) Uiso 1 1 d . . . . .
H3C H 0.490(3) 1.095(3) 0.098(2) 0.073(8) Uiso 1 1 d . . . . .
H4C H 0.263(3) 0.742(4) 0.011(2) 0.098(10) Uiso 1 1 d . . . . .
H4D H 0.232(4) 0.895(5) -0.035(3) 0.144(16) Uiso 1 1 d . . . . .
H4E H 0.196(6) 0.875(5) 0.058(4) 0.19(2) Uiso 1 1 d . . . . .
H6 H 0.723(2) -0.004(3) 0.4343(18) 0.070(7) Uiso 1 1 d . . . . .
H7 H 0.706(3) -0.007(3) 0.589(2) 0.084(8) Uiso 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
O2 C5 1.244(2) . ?
N4 C2 1.332(2) . ?
N4 H4A 0.89(2) . ?
N4 H4B 0.90(2) . ?
O3 H3 0.8200 . ?
O3 C8 1.286(3) . ?
N3 C2 1.353(2) . ?
N3 C1 1.327(2) . ?
N2 C1 1.332(2) . ?
N2 H2A 0.87(2) . ?
N2 H2B 0.88(2) . ?
N5 C2 1.322(2) . ?
N5 C3 1.453(2) . ?
N5 C4 1.452(3) . ?
O1 C5 1.254(2) . ?
N1 C1 1.330(2) . ?
N1 H1A 0.89(2) . ?
N1 H1B 0.88(2) . ?
C5 C6 1.484(3) . ?
O4 C8 1.209(3) . ?
C3 H3A 0.95(3) . ?
C3 H3B 0.95(2) . ?
C3 H3C 0.94(3) . ?
C8 C7 1.480(3) . ?
C6 C7 1.327(3) . ?
C6 H6 0.94(3) . ?
C7 H7 0.91(3) . ?
C4 H4C 0.90(3) . ?
C4 H4D 0.89(4) . ?
C4 H4E 1.04(6) . ?

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
C2 N4 H4A 116.9(14) . . ?
C2 N4 H4B 125.6(14) . . ?
H4A N4 H4B 117(2) . . ?
C8 O3 H3 109.5 . . ?
C1 N3 C2 120.37(15) . . ?
C1 N2 H2A 120.0(13) . . ?
C1 N2 H2B 118.7(15) . . ?
H2A N2 H2B 121(2) . . ?
C2 N5 C3 121.88(17) . . ?
C2 N5 C4 121.25(18) . . ?
C4 N5 C3 115.97(19) . . ?
C1 N1 H1A 119.6(14) . . ?
C1 N1 H1B 118.8(14) . . ?
H1A N1 H1B 119(2) . . ?
N4 C2 N3 120.96(16) . . ?
N5 C2 N4 119.52(16) . . ?
N5 C2 N3 119.14(16) . . ?
N3 C1 N2 118.74(16) . . ?
N3 C1 N1 123.82(16) . . ?
N1 C1 N2 117.40(17) . . ?
O2 C5 O1 123.62(17) . . ?
O2 C5 C6 117.63(17) . . ?
O1 C5 C6 118.72(17) . . ?
N5 C3 H3A 109.4(15) . . ?
N5 C3 H3B 108.1(14) . . ?
N5 C3 H3C 109.2(16) . . ?
H3A C3 H3B 113(2) . . ?
H3A C3 H3C 107(2) . . ?
H3B C3 H3C 110(2) . . ?
O3 C8 C7 119.50(19) . . ?
O4 C8 O3 121.0(2) . . ?
O4 C8 C7 119.5(2) . . ?
C5 C6 H6 112.1(15) . . ?
C7 C6 C5 130.7(2) . . ?
C7 C6 H6 117.1(15) . . ?
C8 C7 H7 111.7(18) . . ?
C6 C7 C8 131.7(2) . . ?
C6 C7 H7 116.6(18) . . ?
N5 C4 H4C 114(2) . . ?
N5 C4 H4D 109(3) . . ?
N5 C4 H4E 112(3) . . ?
H4C C4 H4D 113(3) . . ?
H4C C4 H4E 111(3) . . ?
H4D C4 H4E 96(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
O2 C5 C6 C7 -179.7(3) . . . . ?
O3 C8 C7 C6 -4.5(5) . . . . ?
O1 C5 C6 C7 2.2(4) . . . . ?
C2 N3 C1 N2 -162.77(18) . . . . ?
C2 N3 C1 N1 19.6(3) . . . . ?
C1 N3 C2 N4 51.1(3) . . . . ?
C1 N3 C2 N5 -136.06(18) . . . . ?
C5 C6 C7 C8 2.9(5) . . . . ?
O4 C8 C7 C6 176.1(3) . . . . ?
C3 N5 C2 N4 -0.1(3) . . . . ?
C3 N5 C2 N3 -173.03(19) . . . . ?
C4 N5 C2 N4 -168.8(2) . . . . ?
C4 N5 C2 N3 18.3(3) . . . . ?

_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 1.381
_oxdiff_exptl_absorpt_empirical_full_min 0.846
####################################################################### 
# 
# 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_met-mln_2
_database_code_depnum_ccdc_archive 'CCDC 2133373'
loop_
_audit_author_name
_audit_author_address
'Luan F. Diniz'
;Universidade Federal de Minas Gerais
Brazil
;
_audit_update_record             
;
2022-06-05 deposited with the CCDC.	2022-06-23 downloaded from the CCDC.
;
_audit_creation_date             2022-05-28
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        'Metformin malonate'
_chemical_formula_moiety         'C3 H3 O4, C4 H12 N5'
_chemical_formula_sum            'C7 H15 N5 O4'
_chemical_formula_weight         233.24
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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                   12.5378(5)
_cell_length_b                   5.0060(2)
_cell_length_c                   17.6122(7)
_cell_angle_alpha                90
_cell_angle_beta                 91.971(4)
_cell_angle_gamma                90
_cell_volume                     1104.76(8)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3700
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      30.9980
_cell_measurement_theta_min      2.7800
_shelx_estimated_absorpt_T_max   0.980
_shelx_estimated_absorpt_T_min   0.953
_exptl_absorpt_coefficient_mu    0.115
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86106
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.42a (Rigaku Oxford Diffraction, 2019)
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    1.402
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       prism
_exptl_crystal_F_000             496
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.18
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0378
_diffrn_reflns_av_unetI/netI     0.0230
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       22
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_number            15260
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.471
_diffrn_reflns_theta_min         2.314
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4186
_diffrn_detector_type            Atlas
_diffrn_measured_fraction_theta_full 0.999
_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    -98.00  15.00   1.00   22.50    --  -19.10 -77.00-180.00  113
  2  ω    -49.00  55.00   1.00   22.50    --  -19.10  57.00 -60.00  104
  3  ω   -109.00 -34.00   1.00   22.50    --  -19.10-179.00   0.00   75
  4  ω    -53.00  60.00   1.00   22.50    --  -19.10  77.00  30.00  113
  5  ω    -98.00  15.00   1.00   22.50    --  -19.10 -77.00 -90.00  113
  6  ω     56.00 111.00   1.00   22.50    --   21.29 179.00  90.00   55
  7  ω   -109.00 -57.00   1.00   22.50    --  -19.10-179.00  90.00   52
  8  ω    -95.00   7.00   1.00   22.50    --  -19.10 -38.00   0.00  102
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0016030000
_diffrn_orient_matrix_UB_12      0.0808587000
_diffrn_orient_matrix_UB_13      -0.0330197000
_diffrn_orient_matrix_UB_21      -0.0063382000
_diffrn_orient_matrix_UB_22      -0.1153084000
_diffrn_orient_matrix_UB_23      -0.0231090000
_diffrn_orient_matrix_UB_31      -0.0562280000
_diffrn_orient_matrix_UB_32      0.0153221000
_diffrn_orient_matrix_UB_33      0.0002675000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2032
_reflns_number_total             2544
_reflns_odcompleteness_completeness 99.89
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.44
_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 1.171.40.42a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.42a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.42a (Rigaku OD, 2019)'
_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 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.181
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.043
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.030
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     202
_refine_ls_number_reflns         2544
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0505
_refine_ls_R_factor_gt           0.0389
_refine_ls_restrained_S_all      1.030
_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)+(0.0621P)²+0.1473P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1042
_refine_ls_wR_factor_ref         0.1139
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.5 times of:
  All O(H) groups
2.a Idealised tetrahedral OH refined as rotating group:
 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
O1 O 0.74471(8) 0.5909(2) 0.68548(6) 0.0503(3) Uani 1 1 d . . . . .
O2 O 0.68389(8) 0.3222(2) 0.77387(6) 0.0483(3) Uani 1 1 d . . . . .
O3 O 0.92386(10) 0.5187(3) 0.63304(7) 0.0627(4) Uani 1 1 d . . . . .
H3 H 0.864659 0.579945 0.641139 0.094 Uiso 1 1 calc R U . . .
O4 O 1.03091(9) 0.2133(2) 0.68165(7) 0.0580(3) Uani 1 1 d . . . . .
C5 C 0.75457(10) 0.3963(3) 0.73092(8) 0.0351(3) Uani 1 1 d . . . . .
C6 C 0.85841(10) 0.2407(3) 0.73245(8) 0.0367(3) Uani 1 1 d . . . . .
C7 C 0.94498(11) 0.3248(3) 0.68030(8) 0.0405(3) Uani 1 1 d . . . . .
N1 N 0.54577(9) 0.5408(3) 0.60251(7) 0.0399(3) Uani 1 1 d . . . . .
N2 N 0.46408(10) 0.2638(3) 0.68539(7) 0.0407(3) Uani 1 1 d . . . . .
N3 N 0.39754(8) 0.3172(2) 0.55981(6) 0.0353(3) Uani 1 1 d . . . . .
N4 N 0.23985(10) 0.3733(3) 0.62501(7) 0.0405(3) Uani 1 1 d . . . . .
N5 N 0.24615(9) 0.0920(2) 0.52192(7) 0.0404(3) Uani 1 1 d . . . . .
C1 C 0.46698(9) 0.3739(3) 0.61675(7) 0.0307(3) Uani 1 1 d . . . . .
C2 C 0.29559(10) 0.2569(2) 0.57106(7) 0.0309(3) Uani 1 1 d . . . . .
C3 C 0.13102(13) 0.0527(5) 0.52010(11) 0.0580(5) Uani 1 1 d . . . . .
C4 C 0.30542(14) -0.0720(4) 0.47018(10) 0.0490(4) Uani 1 1 d . . . . .
H1A H 0.6028(13) 0.559(3) 0.6333(9) 0.041(4) Uiso 1 1 d . . . . .
H1B H 0.5552(14) 0.586(3) 0.5547(11) 0.051(5) Uiso 1 1 d . . . . .
H2A H 0.5165(15) 0.282(3) 0.7165(10) 0.047(5) Uiso 1 1 d . . . . .
H2B H 0.4144(15) 0.141(4) 0.6938(10) 0.049(4) Uiso 1 1 d . . . . .
H4A H 0.1760(17) 0.321(4) 0.6375(10) 0.058(5) Uiso 1 1 d . . . . .
H4B H 0.2696(15) 0.494(4) 0.6539(10) 0.050(5) Uiso 1 1 d . . . . .
H4C H 0.2952(18) -0.005(4) 0.4177(13) 0.083(7) Uiso 1 1 d . . . . .
H4D H 0.379(2) -0.072(4) 0.4855(13) 0.079(6) Uiso 1 1 d . . . . .
H4E H 0.2743(18) -0.254(5) 0.4709(12) 0.074(6) Uiso 1 1 d . . . . .
H6A H 0.8898(15) 0.244(3) 0.7833(11) 0.054(5) Uiso 1 1 d . . . . .
H6B H 0.8407(16) 0.059(4) 0.7222(11) 0.066(6) Uiso 1 1 d . . . . .
H3A H 0.0894(19) 0.223(5) 0.5332(12) 0.079(6) Uiso 1 1 d . . . . .
H3B H 0.106(2) 0.005(5) 0.4709(14) 0.089(7) Uiso 1 1 d . . . . .
H3C H 0.110(2) -0.054(5) 0.5593(15) 0.092(8) Uiso 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
O1 C5 1.2642(17) . ?
O2 C5 1.2415(17) . ?
O3 H3 0.8200 . ?
O3 C7 1.3002(19) . ?
O4 C7 1.2128(18) . ?
C5 C6 1.5166(18) . ?
C6 C7 1.5058(19) . ?
C6 H6A 0.965(19) . ?
C6 H6B 0.95(2) . ?
N1 C1 1.3244(17) . ?
N1 H1A 0.886(17) . ?
N1 H1B 0.885(19) . ?
N2 C1 1.3304(17) . ?
N2 H2A 0.846(19) . ?
N2 H2B 0.892(19) . ?
N3 C1 1.3357(16) . ?
N3 C2 1.3348(16) . ?
N4 C2 1.3330(17) . ?
N4 H4A 0.88(2) . ?
N4 H4B 0.86(2) . ?
N5 C2 1.3333(16) . ?
N5 C3 1.4560(19) . ?
N5 C4 1.4501(19) . ?
C3 H3A 1.03(2) . ?
C3 H3B 0.94(2) . ?
C3 H3C 0.92(3) . ?
C4 H4C 0.99(2) . ?
C4 H4D 0.96(2) . ?
C4 H4E 0.99(2) . ?

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
C7 O3 H3 109.5 . . ?
O1 C5 C6 118.17(12) . . ?
O2 C5 O1 124.04(13) . . ?
O2 C5 C6 117.78(12) . . ?
C5 C6 H6A 109.2(11) . . ?
C5 C6 H6B 107.0(12) . . ?
C7 C6 C5 118.82(12) . . ?
C7 C6 H6A 106.4(11) . . ?
C7 C6 H6B 108.6(11) . . ?
H6A C6 H6B 106.1(15) . . ?
O3 C7 C6 117.64(13) . . ?
O4 C7 O3 121.16(13) . . ?
O4 C7 C6 121.19(14) . . ?
C1 N1 H1A 122.7(10) . . ?
C1 N1 H1B 117.9(12) . . ?
H1A N1 H1B 115.1(16) . . ?
C1 N2 H2A 119.9(12) . . ?
C1 N2 H2B 118.6(11) . . ?
H2A N2 H2B 119.9(16) . . ?
C2 N3 C1 122.65(11) . . ?
C2 N4 H4A 123.7(12) . . ?
C2 N4 H4B 119.9(12) . . ?
H4A N4 H4B 115.9(17) . . ?
C2 N5 C3 122.43(12) . . ?
C2 N5 C4 121.43(12) . . ?
C4 N5 C3 116.03(13) . . ?
N1 C1 N2 118.52(12) . . ?
N1 C1 N3 117.60(12) . . ?
N2 C1 N3 123.81(12) . . ?
N4 C2 N3 122.34(12) . . ?
N4 C2 N5 119.34(12) . . ?
N5 C2 N3 118.03(11) . . ?
N5 C3 H3A 113.1(13) . . ?
N5 C3 H3B 110.5(15) . . ?
N5 C3 H3C 111.5(16) . . ?
H3A C3 H3B 105.2(19) . . ?
H3A C3 H3C 99.0(19) . . ?
H3B C3 H3C 117(2) . . ?
N5 C4 H4C 110.1(13) . . ?
N5 C4 H4D 109.6(14) . . ?
N5 C4 H4E 107.6(12) . . ?
H4C C4 H4D 111.0(19) . . ?
H4C C4 H4E 106.5(18) . . ?
H4D C4 H4E 111.9(19) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C5 C6 C7 0.22(19) . . . . ?
O2 C5 C6 C7 179.36(13) . . . . ?
C5 C6 C7 O3 -3.9(2) . . . . ?
C5 C6 C7 O4 177.03(13) . . . . ?
C1 N3 C2 N4 36.4(2) . . . . ?
C1 N3 C2 N5 -149.73(13) . . . . ?
C2 N3 C1 N1 -149.86(13) . . . . ?
C2 N3 C1 N2 33.2(2) . . . . ?
C3 N5 C2 N3 -168.06(15) . . . . ?
C3 N5 C2 N4 6.0(2) . . . . ?
C4 N5 C2 N3 15.9(2) . . . . ?
C4 N5 C2 N4 -170.01(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 1.152
_oxdiff_exptl_absorpt_empirical_full_min 0.881
####################################################################### 
# 
# 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_met-sac_2
_database_code_depnum_ccdc_archive 'CCDC 2133374'
loop_
_audit_author_name
_audit_author_address
'Luan F. Diniz'
;Universidade Federal de Minas Gerais
Brazil
;
_audit_update_record             
;
2022-06-05 deposited with the CCDC.	2022-06-23 downloaded from the CCDC.
;
_audit_creation_date             2022-05-28
_audit_creation_method           
;
Olex2 1.3
(compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6408)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        'Metformin saccharinate'
_chemical_formula_moiety         'C7 H4 N O3 S, C4 H12 N5'
_chemical_formula_sum            'C11 H16 N6 O3 S'
_chemical_formula_weight         312.36
_chemical_melting_point          ?
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.1246 0.1234 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_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/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   7.7925(4)
_cell_length_b                   15.5421(6)
_cell_length_c                   11.8517(6)
_cell_angle_alpha                90
_cell_angle_beta                 92.794(5)
_cell_angle_gamma                90
_cell_volume                     1433.67(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    3754
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      30.3850
_cell_measurement_theta_min      2.9190
_shelx_estimated_absorpt_T_max   0.964
_shelx_estimated_absorpt_T_min   0.904
_exptl_absorpt_coefficient_mu    0.247
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.83868
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.42a (Rigaku Oxford Diffraction, 2019)
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    1.447
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             656
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.15
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0326
_diffrn_reflns_av_unetI/netI     0.0261
_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       -9
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -19
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            12555
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.372
_diffrn_reflns_theta_min         2.163
_diffrn_ambient_temperature      293(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 10.4186
_diffrn_detector_type            Atlas
_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    -77.00  11.00   1.00   11.47    --  -19.26 -77.00 -90.00   88
  2  ω    -49.00  55.00   1.00   11.47    --  -19.26  57.00 120.00  104
  3  ω    -95.00 -35.00   1.00   11.47    --  -19.26-179.00 -90.00   60
  4  ω    -49.00   7.00   1.00   11.47    --  -19.26 -77.00 150.00   56
  5  ω    -46.00  55.00   1.00   11.47    --  -19.26  38.00-120.00  101
  6  ω    -57.00  -9.00   1.00   11.47    --   21.29 -77.00  30.00   48
  7  ω     19.00  44.00   1.00   11.47    --   21.29 -57.00-120.00   25
  8  ω     22.00  54.00   1.00   11.47    --   21.29 -77.00  30.00   32
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Atlas, Gemini ultra'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0068850000
_diffrn_orient_matrix_UB_12      0.0434542000
_diffrn_orient_matrix_UB_13      -0.0175251000
_diffrn_orient_matrix_UB_21      -0.0036354000
_diffrn_orient_matrix_UB_22      0.0137142000
_diffrn_orient_matrix_UB_23      0.0568931000
_diffrn_orient_matrix_UB_31      0.0908222000
_diffrn_orient_matrix_UB_32      -0.0027483000
_diffrn_orient_matrix_UB_33      0.0065223000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Enhance (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2367
_reflns_number_total             2934
_reflns_odcompleteness_completeness 99.96
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     30.44
_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 1.171.40.42a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.42a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.42a (Rigaku OD, 2019)'
_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 2014/5 (Sheldrick, 2014)'
_refine_diff_density_max         0.292
_refine_diff_density_min         -0.337
_refine_diff_density_rms         0.048
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_hydrogen_treatment    refall
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         2934
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0536
_refine_ls_R_factor_gt           0.0413
_refine_ls_restrained_S_all      1.075
_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)+(0.0478P)²+0.6898P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1033
_refine_ls_wR_factor_ref         0.1117
_refine_special_details          ?
_olex2_refinement_description    
;
;
_atom_sites_solution_hydrogens   difmap
_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
S1 S 0.30388(7) 0.49394(3) 0.17909(4) 0.03458(17) Uani 1 1 d . . . . .
O1 O 0.2042(2) 0.37055(10) 0.42824(12) 0.0456(4) Uani 1 1 d . . . . .
O2 O 0.1725(2) 0.52450(12) 0.09962(15) 0.0578(5) Uani 1 1 d . . . . .
O3 O 0.4582(2) 0.54499(10) 0.18500(15) 0.0530(5) Uani 1 1 d . . . . .
N6 N 0.2309(2) 0.48033(11) 0.30231(14) 0.0348(4) Uani 1 1 d . . . . .
C5 C 0.2423(2) 0.39706(13) 0.33440(16) 0.0313(4) Uani 1 1 d . . . . .
C6 C 0.3088(2) 0.33919(12) 0.24574(16) 0.0290(4) Uani 1 1 d . . . . .
C7 C 0.3517(2) 0.38523(12) 0.15161(16) 0.0304(4) Uani 1 1 d . . . . .
C8 C 0.4190(3) 0.34688(15) 0.05851(19) 0.0415(5) Uani 1 1 d . . . . .
C9 C 0.4416(3) 0.25888(16) 0.0623(2) 0.0500(6) Uani 1 1 d . . . . .
C10 C 0.3981(3) 0.21150(15) 0.1555(2) 0.0487(6) Uani 1 1 d . . . . .
C11 C 0.3323(3) 0.25090(14) 0.24857(19) 0.0401(5) Uani 1 1 d . . . . .
N1 N 0.1556(3) 0.50094(14) 0.6033(2) 0.0478(5) Uani 1 1 d . . . . .
N2 N 0.3661(3) 0.57628(16) 0.52105(19) 0.0486(5) Uani 1 1 d . . . . .
N3 N 0.2615(2) 0.63218(11) 0.68007(15) 0.0393(4) Uani 1 1 d . . . . .
N4 N 0.2024(3) 0.55036(13) 0.83959(18) 0.0418(5) Uani 1 1 d . . . . .
N5 N 0.1316(3) 0.69378(11) 0.82838(15) 0.0423(4) Uani 1 1 d . . . . .
C1 C 0.2583(3) 0.56929(14) 0.60493(17) 0.0359(5) Uani 1 1 d . . . . .
C2 C 0.1963(3) 0.62391(13) 0.78206(17) 0.0340(4) Uani 1 1 d . . . . .
C3 C 0.0766(5) 0.6953(2) 0.9438(2) 0.0574(7) Uani 1 1 d . . . . .
C4 C 0.1258(5) 0.77563(18) 0.7684(3) 0.0595(7) Uani 1 1 d . . . . .
H8 H 0.449(3) 0.3794(15) -0.002(2) 0.043(6) Uiso 1 1 d . . . . .
H11 H 0.302(3) 0.2165(15) 0.313(2) 0.042(6) Uiso 1 1 d . . . . .
H9 H 0.489(3) 0.2299(19) 0.001(2) 0.063(8) Uiso 1 1 d . . . . .
H1A H 0.072(4) 0.5003(16) 0.646(2) 0.053(8) Uiso 1 1 d . . . . .
H1B H 0.160(3) 0.4651(18) 0.553(3) 0.054(8) Uiso 1 1 d . . . . .
H10 H 0.415(3) 0.1501(18) 0.155(2) 0.054(7) Uiso 1 1 d . . . . .
H2A H 0.350(4) 0.549(2) 0.463(3) 0.069(10) Uiso 1 1 d . . . . .
H2B H 0.436(4) 0.618(2) 0.524(3) 0.078(11) Uiso 1 1 d . . . . .
H4A H 0.267(4) 0.5115(18) 0.818(2) 0.055(8) Uiso 1 1 d . . . . .
H4B H 0.166(4) 0.543(2) 0.903(3) 0.069(9) Uiso 1 1 d . . . . .
H4C H 0.195(5) 0.775(2) 0.711(3) 0.096(13) Uiso 1 1 d . . . . .
H4D H 0.022(6) 0.793(3) 0.763(4) 0.125(17) Uiso 1 1 d . . . . .
H3A H -0.038(5) 0.714(3) 0.948(3) 0.107(13) Uiso 1 1 d . . . . .
H3B H 0.128(6) 0.657(3) 0.984(4) 0.145(18) Uiso 1 1 d . . . . .
H4E H 0.179(6) 0.825(3) 0.812(4) 0.140(17) Uiso 1 1 d . . . . .
H3C H 0.131(5) 0.746(3) 0.980(3) 0.109(13) Uiso 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
S1 O2 1.4375(18) . ?
S1 O3 1.4394(17) . ?
S1 N6 1.6069(17) . ?
S1 C7 1.7638(19) . ?
O1 C5 1.236(2) . ?
N6 C5 1.351(3) . ?
C5 C6 1.495(3) . ?
C6 C7 1.380(3) . ?
C6 C11 1.385(3) . ?
C7 C8 1.380(3) . ?
C8 C9 1.379(3) . ?
C8 H8 0.92(2) . ?
C9 C10 1.384(4) . ?
C9 H9 0.94(3) . ?
C10 C11 1.381(3) . ?
C10 H10 0.96(3) . ?
C11 H11 0.97(2) . ?
N1 C1 1.330(3) . ?
N1 H1A 0.85(3) . ?
N1 H1B 0.82(3) . ?
N2 C1 1.337(3) . ?
N2 H2A 0.82(3) . ?
N2 H2B 0.85(3) . ?
N3 C1 1.322(3) . ?
N3 C2 1.340(3) . ?
N4 C2 1.331(3) . ?
N4 H4A 0.83(3) . ?
N4 H4B 0.82(3) . ?
N5 C2 1.327(3) . ?
N5 C3 1.454(3) . ?
N5 C4 1.457(3) . ?
C3 H3A 0.94(4) . ?
C3 H3B 0.85(5) . ?
C3 H3C 0.98(4) . ?
C4 H4C 0.88(4) . ?
C4 H4D 0.85(5) . ?
C4 H4E 1.00(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 S1 O3 114.58(11) . . ?
O2 S1 N6 111.51(10) . . ?
O2 S1 C7 110.22(11) . . ?
O3 S1 N6 111.11(10) . . ?
O3 S1 C7 110.70(10) . . ?
N6 S1 C7 97.42(9) . . ?
C5 N6 S1 111.14(13) . . ?
O1 C5 N6 123.89(18) . . ?
O1 C5 C6 122.59(18) . . ?
N6 C5 C6 113.51(17) . . ?
C7 C6 C5 111.23(17) . . ?
C7 C6 C11 119.76(18) . . ?
C11 C6 C5 129.00(18) . . ?
C6 C7 S1 106.59(14) . . ?
C8 C7 S1 130.80(17) . . ?
C8 C7 C6 122.60(19) . . ?
C7 C8 H8 120.5(15) . . ?
C9 C8 C7 117.1(2) . . ?
C9 C8 H8 122.4(15) . . ?
C8 C9 C10 121.2(2) . . ?
C8 C9 H9 120.1(18) . . ?
C10 C9 H9 118.7(18) . . ?
C9 C10 H10 119.0(15) . . ?
C11 C10 C9 121.1(2) . . ?
C11 C10 H10 119.9(15) . . ?
C6 C11 H11 122.0(14) . . ?
C10 C11 C6 118.3(2) . . ?
C10 C11 H11 119.8(14) . . ?
C1 N1 H1A 118.8(18) . . ?
C1 N1 H1B 120.7(19) . . ?
H1A N1 H1B 119(3) . . ?
C1 N2 H2A 121(2) . . ?
C1 N2 H2B 118(2) . . ?
H2A N2 H2B 120(3) . . ?
C1 N3 C2 122.77(19) . . ?
C2 N4 H4A 118.0(19) . . ?
C2 N4 H4B 125(2) . . ?
H4A N4 H4B 116(3) . . ?
C2 N5 C3 122.6(2) . . ?
C2 N5 C4 121.0(2) . . ?
C3 N5 C4 116.2(2) . . ?
N1 C1 N2 117.0(2) . . ?
N3 C1 N1 126.3(2) . . ?
N3 C1 N2 116.7(2) . . ?
N4 C2 N3 122.6(2) . . ?
N5 C2 N3 117.58(19) . . ?
N5 C2 N4 119.7(2) . . ?
N5 C3 H3A 113(2) . . ?
N5 C3 H3B 111(3) . . ?
N5 C3 H3C 106(2) . . ?
H3A C3 H3B 127(4) . . ?
H3A C3 H3C 97(3) . . ?
H3B C3 H3C 98(4) . . ?
N5 C4 H4C 111(2) . . ?
N5 C4 H4D 109(3) . . ?
N5 C4 H4E 115(3) . . ?
H4C C4 H4D 124(4) . . ?
H4C C4 H4E 99(3) . . ?
H4D C4 H4E 99(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
S1 N6 C5 O1 175.57(17) . . . . ?
S1 N6 C5 C6 -3.4(2) . . . . ?
S1 C7 C8 C9 -179.87(18) . . . . ?
O1 C5 C6 C7 -176.19(19) . . . . ?
O1 C5 C6 C11 2.9(3) . . . . ?
O2 S1 N6 C5 117.74(16) . . . . ?
O2 S1 C7 C6 -117.08(15) . . . . ?
O2 S1 C7 C8 63.2(2) . . . . ?
O3 S1 N6 C5 -113.09(16) . . . . ?
O3 S1 C7 C6 115.10(15) . . . . ?
O3 S1 C7 C8 -64.7(2) . . . . ?
N6 S1 C7 C6 -0.85(16) . . . . ?
N6 S1 C7 C8 179.4(2) . . . . ?
N6 C5 C6 C7 2.8(2) . . . . ?
N6 C5 C6 C11 -178.1(2) . . . . ?
C5 C6 C7 S1 -0.9(2) . . . . ?
C5 C6 C7 C8 178.86(19) . . . . ?
C5 C6 C11 C10 -179.3(2) . . . . ?
C6 C7 C8 C9 0.4(3) . . . . ?
C7 S1 N6 C5 2.53(16) . . . . ?
C7 C6 C11 C10 -0.3(3) . . . . ?
C7 C8 C9 C10 0.1(4) . . . . ?
C8 C9 C10 C11 -0.8(4) . . . . ?
C9 C10 C11 C6 0.8(4) . . . . ?
C11 C6 C7 S1 179.90(17) . . . . ?
C11 C6 C7 C8 -0.3(3) . . . . ?
C1 N3 C2 N4 34.7(3) . . . . ?
C1 N3 C2 N5 -148.9(2) . . . . ?
C2 N3 C1 N1 19.5(4) . . . . ?
C2 N3 C1 N2 -162.2(2) . . . . ?
C3 N5 C2 N3 -172.3(2) . . . . ?
C3 N5 C2 N4 4.2(3) . . . . ?
C4 N5 C2 N3 2.4(3) . . . . ?
C4 N5 C2 N4 178.9(3) . . . . ?

_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 1.218
_oxdiff_exptl_absorpt_empirical_full_min 0.831
