# 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 2020

####################################################################### 
# 
# 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_6MMCN
_database_code_depnum_ccdc_archive 'CCDC 1856540'
loop_
_audit_author_name
_audit_author_address
'Frank R. Fronczek'
;Department of Chemistry, Louisiana State University, Baton Rouge, LA 70803, USA
United States of America
;
_audit_update_record             
;
2018-07-18 deposited with the CCDC.	2020-02-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H16 Cu N5 O5 S, N O3'
_chemical_formula_sum            'C13 H16 Cu N6 O8 S'
_chemical_formula_weight         479.92

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'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   9.0641(5)
_cell_length_b                   10.0930(6)
_cell_length_c                   10.4290(6)
_cell_angle_alpha                73.0502(18)
_cell_angle_beta                 73.9551(16)
_cell_angle_gamma                85.5174(17)
_cell_volume                     877.09(9)
_cell_formula_units_Z            2
_cell_measurement_temperature    90.0(5)
_cell_measurement_reflns_used    5720
_cell_measurement_theta_min      3.15
_cell_measurement_theta_max      33.75

_exptl_crystal_description       fragment
_exptl_crystal_colour            'emerald green'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.817
_exptl_crystal_F_000             490
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.150
_exptl_crystal_size_min          0.130
_exptl_absorpt_coefficient_mu    1.425
_shelx_estimated_absorpt_T_min   0.754
_shelx_estimated_absorpt_T_max   0.836
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.762
_exptl_absorpt_correction_T_max  0.836
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2004)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      90.0(5)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  'TRIUMPH curved graphite'
_diffrn_measurement_device_type  'Bruker Kappa APEX-II DUO'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10516
_diffrn_reflns_av_unetI/netI     0.0244
_diffrn_reflns_av_R_equivalents  0.0125
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.109
_diffrn_reflns_theta_max         33.784
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measured_fraction_theta_full 0.995
_diffrn_reflns_Laue_measured_fraction_max 0.992
_diffrn_reflns_Laue_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.992
_diffrn_reflns_point_group_measured_fraction_full 0.995
_reflns_number_total             6992
_reflns_number_gt                6192
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0323P)²+0.3847P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6992
_refine_ls_number_parameters     279
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0318
_refine_ls_R_factor_gt           0.0259
_refine_ls_wR_factor_ref         0.0670
_refine_ls_wR_factor_gt          0.0644
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_restrained_S_all      1.039
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.77301(2) 0.54159(2) 0.54233(2) 0.00887(4) Uani 1 1 d . . . . .
S1 S 0.96933(3) 0.69865(3) 0.46235(3) 0.01061(5) Uani 1 1 d . . . . .
O1 O 0.63046(9) 0.38940(9) 0.61568(8) 0.01235(14) Uani 1 1 d . . . . .
O2 O 0.77267(10) 0.52560(10) 0.35986(9) 0.01489(15) Uani 1 1 d . . . . .
H21 H 0.829(2) 0.5664(19) 0.287(2) 0.022 Uiso 1 1 d . U . . .
H22 H 0.712(2) 0.479(2) 0.347(2) 0.022 Uiso 1 1 d . U . . .
O3 O 0.58571(10) 0.70688(10) 0.51713(9) 0.01655(16) Uani 1 1 d . . . . .
O4 O 0.41294(12) 0.63198(13) 0.71438(10) 0.0274(2) Uani 1 1 d . . . . .
O5 O 0.50007(15) 0.84130(12) 0.64949(14) 0.0355(3) Uani 1 1 d . . . . .
N1 N 0.45494(10) 0.23534(9) 0.76348(9) 0.00949(15) Uani 1 1 d . . . . .
H1N H 0.4385(18) 0.2274(17) 0.6877(17) 0.011 Uiso 1 1 d . U . . .
N2 N 0.78008(10) 0.53564(10) 0.73193(9) 0.00969(15) Uani 1 1 d . . . . .
N3 N 0.88013(11) 0.62637(10) 0.74047(9) 0.01131(16) Uani 1 1 d . . . . .
H3N H 0.8835(19) 0.6283(17) 0.8221(18) 0.014 Uiso 1 1 d . U . . .
N4 N 1.07245(11) 0.78495(10) 0.64012(10) 0.01232(16) Uani 1 1 d . . . . .
H4N H 1.075(2) 0.7720(18) 0.7229(19) 0.015 Uiso 1 1 d . U . . .
N5 N 0.49856(11) 0.72786(11) 0.62743(11) 0.01572(18) Uani 1 1 d . . . . .
C1 C 0.56396(12) 0.32968(11) 0.74055(11) 0.00939(16) Uani 1 1 d . . . . .
C2 C 0.59651(12) 0.35073(11) 0.86136(10) 0.00965(16) Uani 1 1 d . . . . .
C3 C 0.52341(12) 0.26940(11) 0.99156(11) 0.01091(17) Uani 1 1 d . . . . .
H3 H 0.5482 0.2807 1.0705 0.013 Uiso 1 1 calc R U . . .
C4 C 0.41210(12) 0.16912(11) 1.01092(11) 0.01005(17) Uani 1 1 d . . . . .
C5 C 0.33298(13) 0.08603(12) 1.14388(11) 0.01334(19) Uani 1 1 d . . . . .
H5A H 0.3549 0.0946 1.2251 0.016 Uiso 1 1 calc R U . . .
C6 C 0.22427(13) -0.00700(12) 1.15450(12) 0.01489(19) Uani 1 1 d . . . . .
H6 H 0.1711 -0.0630 1.2435 0.018 Uiso 1 1 calc R U . . .
C7 C 0.19126(13) -0.01982(12) 1.03454(11) 0.01291(18) Uani 1 1 d . . . . .
H7 H 0.1160 -0.0852 1.0444 0.015 Uiso 1 1 calc R U . . .
C8 C 0.26485(12) 0.05966(11) 0.90265(11) 0.01023(17) Uani 1 1 d . . . . .
C9 C 0.37650(11) 0.15443(11) 0.89220(10) 0.00894(16) Uani 1 1 d . . . . .
C10 C 0.70627(12) 0.45273(11) 0.84896(10) 0.01030(17) Uani 1 1 d . . . . .
H10 H 0.7257 0.4596 0.9318 0.012 Uiso 1 1 calc R U . . .
C11 C 0.97518(12) 0.70448(11) 0.62311(11) 0.00988(17) Uani 1 1 d . . . . .
C12 C 0.22920(13) 0.04592(12) 0.77509(11) 0.01353(19) Uani 1 1 d . . . . .
H12A H 0.1469 -0.0223 0.8023 0.020 Uiso 1 1 calc R U . . .
H12B H 0.3212 0.0153 0.7157 0.020 Uiso 1 1 calc R U . . .
H12C H 0.1962 0.1358 0.7239 0.020 Uiso 1 1 calc R U . . .
C13 C 1.18450(13) 0.87449(12) 0.52510(11) 0.01375(19) Uani 1 1 d . . . . .
H13A H 1.2436 0.8204 0.4640 0.021 Uiso 1 1 calc R U . . .
H13B H 1.2541 0.9136 0.5617 0.021 Uiso 1 1 calc R U . . .
H13C H 1.1311 0.9497 0.4723 0.021 Uiso 1 1 calc R U . . .
N6 N 0.97896(11) 0.67026(10) 0.02541(9) 0.01064(15) Uani 1 1 d . . . . .
O6 O 0.98433(10) 0.67145(9) 0.14404(8) 0.01523(15) Uani 1 1 d . . . . .
O7 O 0.86546(10) 0.61638(9) 0.01238(9) 0.01493(15) Uani 1 1 d . . . . .
O8 O 1.08694(10) 0.72205(10) -0.07803(9) 0.01676(16) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O1 1.9217(8) . ?
Cu1 O2 1.9569(8) . ?
Cu1 N2 1.9794(9) . ?
Cu1 S1 2.2858(3) . ?
Cu1 O3 2.2984(9) . ?
S1 C11 1.7101(10) . ?
O1 C1 1.2600(12) . ?
O2 H21 0.80(2) . ?
O2 H22 0.81(2) . ?
O3 N5 1.2670(13) . ?
O4 N5 1.2560(15) . ?
O5 N5 1.2337(15) . ?
N1 C1 1.3505(13) . ?
N1 C9 1.3779(13) . ?
N1 H1N 0.870(17) . ?
N2 C10 1.2954(13) . ?
N2 N3 1.3752(12) . ?
N3 C11 1.3500(14) . ?
N3 H3N 0.866(17) . ?
N4 C11 1.3232(14) . ?
N4 C13 1.4577(14) . ?
N4 H4N 0.842(18) . ?
C1 C2 1.4460(14) . ?
C2 C3 1.3764(14) . ?
C2 C10 1.4415(14) . ?
C3 C4 1.4181(15) . ?
C3 H3 0.9500 . ?
C4 C9 1.4122(14) . ?
C4 C5 1.4166(15) . ?
C5 C6 1.3742(16) . ?
C5 H5A 0.9500 . ?
C6 C7 1.4066(16) . ?
C6 H6 0.9500 . ?
C7 C8 1.3833(15) . ?
C7 H7 0.9500 . ?
C8 C9 1.4074(14) . ?
C8 C12 1.4985(15) . ?
C10 H10 0.9500 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?
N6 O8 1.2500(12) . ?
N6 O6 1.2551(12) . ?
N6 O7 1.2571(12) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Cu1 O2 85.31(4) . . ?
O1 Cu1 N2 91.07(4) . . ?
O2 Cu1 N2 173.58(4) . . ?
O1 Cu1 S1 171.55(3) . . ?
O2 Cu1 S1 96.06(3) . . ?
N2 Cu1 S1 86.76(3) . . ?
O1 Cu1 O3 94.03(4) . . ?
O2 Cu1 O3 86.98(4) . . ?
N2 Cu1 O3 98.57(3) . . ?
S1 Cu1 O3 94.37(3) . . ?
C11 S1 Cu1 95.53(4) . . ?
C1 O1 Cu1 129.01(7) . . ?
Cu1 O2 H21 125.2(13) . . ?
Cu1 O2 H22 124.3(13) . . ?
H21 O2 H22 110.5(19) . . ?
N5 O3 Cu1 116.99(7) . . ?
C1 N1 C9 125.25(9) . . ?
C1 N1 H1N 113.7(11) . . ?
C9 N1 H1N 121.1(11) . . ?
C10 N2 N3 115.90(9) . . ?
C10 N2 Cu1 127.81(7) . . ?
N3 N2 Cu1 116.23(7) . . ?
C11 N3 N2 119.70(9) . . ?
C11 N3 H3N 121.8(11) . . ?
N2 N3 H3N 118.4(11) . . ?
C11 N4 C13 123.46(9) . . ?
C11 N4 H4N 115.1(12) . . ?
C13 N4 H4N 120.8(12) . . ?
O5 N5 O4 120.59(12) . . ?
O5 N5 O3 119.85(12) . . ?
O4 N5 O3 119.55(11) . . ?
O1 C1 N1 117.03(9) . . ?
O1 C1 C2 125.82(10) . . ?
N1 C1 C2 117.13(9) . . ?
C3 C2 C10 118.98(9) . . ?
C3 C2 C1 119.29(9) . . ?
C10 C2 C1 121.72(9) . . ?
C2 C3 C4 121.71(9) . . ?
C2 C3 H3 119.1 . . ?
C4 C3 H3 119.1 . . ?
C9 C4 C5 118.91(9) . . ?
C9 C4 C3 118.21(9) . . ?
C5 C4 C3 122.86(9) . . ?
C6 C5 C4 119.50(10) . . ?
C6 C5 H5A 120.3 . . ?
C4 C5 H5A 120.3 . . ?
C5 C6 C7 120.45(10) . . ?
C5 C6 H6 119.8 . . ?
C7 C6 H6 119.8 . . ?
C8 C7 C6 122.11(10) . . ?
C8 C7 H7 118.9 . . ?
C6 C7 H7 118.9 . . ?
C7 C8 C9 117.26(10) . . ?
C7 C8 C12 121.97(9) . . ?
C9 C8 C12 120.76(9) . . ?
N1 C9 C8 119.93(9) . . ?
N1 C9 C4 118.30(9) . . ?
C8 C9 C4 121.77(9) . . ?
N2 C10 C2 124.08(9) . . ?
N2 C10 H10 118.0 . . ?
C2 C10 H10 118.0 . . ?
N4 C11 N3 116.13(9) . . ?
N4 C11 S1 122.34(8) . . ?
N3 C11 S1 121.53(8) . . ?
C8 C12 H12A 109.5 . . ?
C8 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C8 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N4 C13 H13A 109.5 . . ?
N4 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
N4 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
O8 N6 O6 119.52(9) . . ?
O8 N6 O7 120.94(9) . . ?
O6 N6 O7 119.55(9) . . ?

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
C10 N2 N3 C11 171.94(10) . . . . ?
Cu1 N2 N3 C11 -5.41(13) . . . . ?
Cu1 O3 N5 O5 115.72(11) . . . . ?
Cu1 O3 N5 O4 -63.23(12) . . . . ?
Cu1 O1 C1 N1 172.47(7) . . . . ?
Cu1 O1 C1 C2 -9.11(16) . . . . ?
C9 N1 C1 O1 176.14(10) . . . . ?
C9 N1 C1 C2 -2.43(16) . . . . ?
O1 C1 C2 C3 -174.51(11) . . . . ?
N1 C1 C2 C3 3.92(15) . . . . ?
O1 C1 C2 C10 4.07(17) . . . . ?
N1 C1 C2 C10 -177.50(10) . . . . ?
C10 C2 C3 C4 178.75(10) . . . . ?
C1 C2 C3 C4 -2.63(16) . . . . ?
C2 C3 C4 C9 -0.30(16) . . . . ?
C2 C3 C4 C5 -178.71(11) . . . . ?
C9 C4 C5 C6 0.25(17) . . . . ?
C3 C4 C5 C6 178.65(11) . . . . ?
C4 C5 C6 C7 -0.10(18) . . . . ?
C5 C6 C7 C8 -0.31(18) . . . . ?
C6 C7 C8 C9 0.53(17) . . . . ?
C6 C7 C8 C12 -179.89(11) . . . . ?
C1 N1 C9 C8 179.89(10) . . . . ?
C1 N1 C9 C4 -0.48(16) . . . . ?
C7 C8 C9 N1 179.25(10) . . . . ?
C12 C8 C9 N1 -0.33(15) . . . . ?
C7 C8 C9 C4 -0.37(16) . . . . ?
C12 C8 C9 C4 -179.95(10) . . . . ?
C5 C4 C9 N1 -179.64(10) . . . . ?
C3 C4 C9 N1 1.89(15) . . . . ?
C5 C4 C9 C8 -0.01(16) . . . . ?
C3 C4 C9 C8 -178.48(10) . . . . ?
N3 N2 C10 C2 179.89(10) . . . . ?
Cu1 N2 C10 C2 -3.12(16) . . . . ?
C3 C2 C10 N2 -179.14(10) . . . . ?
C1 C2 C10 N2 2.27(17) . . . . ?
C13 N4 C11 N3 179.12(10) . . . . ?
C13 N4 C11 S1 -0.78(16) . . . . ?
N2 N3 C11 N4 -177.27(9) . . . . ?
N2 N3 C11 S1 2.63(15) . . . . ?
Cu1 S1 C11 N4 -179.17(9) . . . . ?
Cu1 S1 C11 N3 0.95(9) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H21 N6 0.80(2) 2.63(2) 3.4126(12) 166.8(17) .
O2 H21 O6 0.80(2) 1.87(2) 2.6526(12) 167.0(19) .
O2 H22 O4 0.81(2) 1.99(2) 2.7958(14) 170.7(19) 2_666
N1 H1N O3 0.870(17) 2.113(17) 2.9339(13) 157.2(15) 2_666
N3 H3N N6 0.866(17) 2.649(17) 3.4828(13) 161.8(14) 1_556
N3 H3N O7 0.866(17) 1.914(17) 2.7742(12) 171.9(16) 1_556
N4 H4N O8 0.842(18) 2.019(18) 2.8588(13) 174.6(16) 1_556
C10 H10 O7 0.95 2.55 3.3299(13) 139.7 1_556
C13 H13A O1 0.98 2.57 3.5047(15) 159.8 2_766
C13 H13B O5 0.98 2.61 3.4095(17) 138.6 1_655

_refine_diff_density_max         0.674
_refine_diff_density_min         -0.361
_refine_diff_density_rms         0.075

####################################################################### 
# 
# 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_6MMT
_database_code_depnum_ccdc_archive 'CCDC 1856543'
loop_
_audit_author_name
_audit_author_address
'Frank R. Fronczek'
;Department of Chemistry, Louisiana State University, Baton Rouge, LA 70803, USA
United States of America
;
_audit_update_record             
;
2018-07-18 deposited with the CCDC.	2020-02-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C13 H14 N4 O S'
_chemical_formula_sum            'C13 H14 N4 O S'
_chemical_formula_weight         274.34

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
S S 0.3331 0.5567 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 21/c'
_space_group_name_Hall           '-P 2ybc'

_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.
;

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                   12.9158(3)
_cell_length_b                   7.2797(2)
_cell_length_c                   14.0234(3)
_cell_angle_alpha                90
_cell_angle_beta                 101.086(2)
_cell_angle_gamma                90
_cell_volume                     1293.92(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    90.0(5)
_cell_measurement_reflns_used    4274
_cell_measurement_theta_min      3.49
_cell_measurement_theta_max      68.13

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.408
_exptl_crystal_F_000             576
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.140
_exptl_crystal_size_mid          0.070
_exptl_crystal_size_min          0.030
_exptl_absorpt_coefficient_mu    2.208
_shelx_estimated_absorpt_T_min   0.747
_shelx_estimated_absorpt_T_max   0.937
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.815
_exptl_absorpt_correction_T_max  0.937
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2004)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      90.0(5)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_radiation_source         'I\mS microfocus'
_diffrn_radiation_monochromator  'QUAZAR multilayer optics'
_diffrn_measurement_device_type  'Bruker Kappa APEX-II DUO'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8186
_diffrn_reflns_av_unetI/netI     0.0457
_diffrn_reflns_av_R_equivalents  0.0430
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.487
_diffrn_reflns_theta_max         68.345
_diffrn_reflns_theta_full        66.600
_diffrn_measured_fraction_theta_max 0.984
_diffrn_measured_fraction_theta_full 0.993
_diffrn_reflns_Laue_measured_fraction_max 0.984
_diffrn_reflns_Laue_measured_fraction_full 0.993
_diffrn_reflns_point_group_measured_fraction_max 0.984
_diffrn_reflns_point_group_measured_fraction_full 0.993
_reflns_number_total             2341
_reflns_number_gt                2067
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0475P)²+1.7129P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2341
_refine_ls_number_parameters     183
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0517
_refine_ls_R_factor_gt           0.0462
_refine_ls_wR_factor_ref         0.1197
_refine_ls_wR_factor_gt          0.1163
_refine_ls_goodness_of_fit_ref   1.050
_refine_ls_restrained_S_all      1.050
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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 -0.06011(4) 0.75332(8) 0.43063(4) 0.0210(2) Uani 1 1 d . . . . .
O1 O 0.38337(12) 0.1037(2) 0.47313(12) 0.0208(4) Uani 1 1 d . . . . .
N1 N 0.52834(14) 0.2085(3) 0.42080(13) 0.0136(4) Uani 1 1 d . . . . .
H1N H 0.558(2) 0.106(4) 0.444(2) 0.016 Uiso 1 1 d . U . . .
N2 N 0.21922(14) 0.5784(3) 0.40386(14) 0.0182(4) Uani 1 1 d . . . . .
N3 N 0.12225(15) 0.5913(3) 0.42977(14) 0.0194(4) Uani 1 1 d . . . . .
H3N H 0.100(2) 0.498(4) 0.469(2) 0.023 Uiso 1 1 d . U . . .
N4 N 0.10179(17) 0.8722(3) 0.35577(15) 0.0225(5) Uani 1 1 d . . . . .
H4N H 0.173(2) 0.863(4) 0.352(2) 0.027 Uiso 1 1 d . U . . .
C1 C 0.42784(17) 0.2297(3) 0.43632(15) 0.0147(5) Uani 1 1 d . . . . .
C2 C 0.37736(17) 0.4062(3) 0.40894(15) 0.0148(5) Uani 1 1 d . . . . .
C3 C 0.43083(17) 0.5395(3) 0.37002(15) 0.0143(5) Uani 1 1 d . . . . .
H3 H 0.3977 0.6546 0.3534 0.017 Uiso 1 1 calc R U . . .
C4 C 0.53511(16) 0.5105(3) 0.35366(15) 0.0133(5) Uani 1 1 d . . . . .
C5 C 0.59177(18) 0.6481(3) 0.31439(16) 0.0156(5) Uani 1 1 d . . . . .
H5 H 0.5602 0.7644 0.2974 0.019 Uiso 1 1 calc R U . . .
C6 C 0.69231(17) 0.6136(3) 0.30092(16) 0.0170(5) Uani 1 1 d . . . . .
H6 H 0.7307 0.7065 0.2752 0.020 Uiso 1 1 calc R U . . .
C7 C 0.73817(17) 0.4421(3) 0.32504(16) 0.0161(5) Uani 1 1 d . . . . .
H7 H 0.8077 0.4206 0.3148 0.019 Uiso 1 1 calc R U . . .
C8 C 0.68608(17) 0.3020(3) 0.36344(15) 0.0148(5) Uani 1 1 d . . . . .
C9 C 0.58371(17) 0.3399(3) 0.37911(15) 0.0133(5) Uani 1 1 d . . . . .
C10 C 0.27145(17) 0.4311(3) 0.42939(16) 0.0169(5) Uani 1 1 d . . . . .
H10 H 0.2410 0.3369 0.4620 0.020 Uiso 1 1 calc R U . . .
C11 C 0.06158(18) 0.7422(3) 0.40389(16) 0.0189(5) Uani 1 1 d . . . . .
C12 C 0.73779(18) 0.1189(3) 0.38807(19) 0.0207(5) Uani 1 1 d . . . . .
H12A H 0.8080 0.1194 0.3713 0.031 Uiso 1 1 calc R U . . .
H12B H 0.6947 0.0223 0.3512 0.031 Uiso 1 1 calc R U . . .
H12C H 0.7444 0.0955 0.4578 0.031 Uiso 1 1 calc R U . . .
C13 C 0.0454(2) 1.0396(4) 0.32101(19) 0.0270(6) Uani 1 1 d . . . . .
H13A H -0.0228 1.0079 0.2805 0.041 Uiso 1 1 calc R U . . .
H13B H 0.0871 1.1105 0.2825 0.041 Uiso 1 1 calc R U . . .
H13C H 0.0340 1.1132 0.3766 0.041 Uiso 1 1 calc R U . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
S1 C11 1.686(2) . ?
O1 C1 1.245(3) . ?
N1 C1 1.366(3) . ?
N1 C9 1.389(3) . ?
N1 H1N 0.87(3) . ?
N2 C10 1.281(3) . ?
N2 N3 1.373(3) . ?
N3 C11 1.358(3) . ?
N3 H3N 0.95(3) . ?
N4 C11 1.325(3) . ?
N4 C13 1.455(3) . ?
N4 H4N 0.93(3) . ?
C1 C2 1.459(3) . ?
C2 C3 1.364(3) . ?
C2 C10 1.462(3) . ?
C3 C4 1.425(3) . ?
C3 H3 0.9500 . ?
C4 C9 1.406(3) . ?
C4 C5 1.413(3) . ?
C5 C6 1.371(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.395(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.387(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.409(3) . ?
C8 C12 1.501(3) . ?
C10 H10 0.9500 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 H13A 0.9800 . ?
C13 H13B 0.9800 . ?
C13 H13C 0.9800 . ?

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
C1 N1 C9 124.9(2) . . ?
C1 N1 H1N 113.2(18) . . ?
C9 N1 H1N 121.7(18) . . ?
C10 N2 N3 116.21(19) . . ?
C11 N3 N2 119.6(2) . . ?
C11 N3 H3N 120.6(18) . . ?
N2 N3 H3N 119.7(18) . . ?
C11 N4 C13 123.3(2) . . ?
C11 N4 H4N 117.5(19) . . ?
C13 N4 H4N 118.6(19) . . ?
O1 C1 N1 120.8(2) . . ?
O1 C1 C2 122.6(2) . . ?
N1 C1 C2 116.60(19) . . ?
C3 C2 C1 119.8(2) . . ?
C3 C2 C10 123.7(2) . . ?
C1 C2 C10 116.43(19) . . ?
C2 C3 C4 121.8(2) . . ?
C2 C3 H3 119.1 . . ?
C4 C3 H3 119.1 . . ?
C9 C4 C5 119.1(2) . . ?
C9 C4 C3 118.7(2) . . ?
C5 C4 C3 122.3(2) . . ?
C6 C5 C4 119.9(2) . . ?
C6 C5 H5 120.0 . . ?
C4 C5 H5 120.0 . . ?
C5 C6 C7 120.0(2) . . ?
C5 C6 H6 120.0 . . ?
C7 C6 H6 120.0 . . ?
C8 C7 C6 122.5(2) . . ?
C8 C7 H7 118.7 . . ?
C6 C7 H7 118.7 . . ?
C7 C8 C9 117.1(2) . . ?
C7 C8 C12 121.0(2) . . ?
C9 C8 C12 121.9(2) . . ?
N1 C9 C4 118.31(19) . . ?
N1 C9 C8 120.3(2) . . ?
C4 C9 C8 121.4(2) . . ?
N2 C10 C2 120.8(2) . . ?
N2 C10 H10 119.6 . . ?
C2 C10 H10 119.6 . . ?
N4 C11 N3 116.8(2) . . ?
N4 C11 S1 123.54(19) . . ?
N3 C11 S1 119.60(18) . . ?
C8 C12 H12A 109.5 . . ?
C8 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C8 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N4 C13 H13A 109.5 . . ?
N4 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
N4 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?

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
C10 N2 N3 C11 -179.0(2) . . . . ?
C9 N1 C1 O1 179.1(2) . . . . ?
C9 N1 C1 C2 -1.7(3) . . . . ?
O1 C1 C2 C3 179.2(2) . . . . ?
N1 C1 C2 C3 0.0(3) . . . . ?
O1 C1 C2 C10 1.6(3) . . . . ?
N1 C1 C2 C10 -177.54(19) . . . . ?
C1 C2 C3 C4 1.0(3) . . . . ?
C10 C2 C3 C4 178.3(2) . . . . ?
C2 C3 C4 C9 -0.4(3) . . . . ?
C2 C3 C4 C5 -179.3(2) . . . . ?
C9 C4 C5 C6 0.5(3) . . . . ?
C3 C4 C5 C6 179.4(2) . . . . ?
C4 C5 C6 C7 0.7(3) . . . . ?
C5 C6 C7 C8 -0.4(3) . . . . ?
C6 C7 C8 C9 -1.0(3) . . . . ?
C6 C7 C8 C12 179.7(2) . . . . ?
C1 N1 C9 C4 2.3(3) . . . . ?
C1 N1 C9 C8 -177.9(2) . . . . ?
C5 C4 C9 N1 177.75(19) . . . . ?
C3 C4 C9 N1 -1.2(3) . . . . ?
C5 C4 C9 C8 -2.0(3) . . . . ?
C3 C4 C9 C8 179.1(2) . . . . ?
C7 C8 C9 N1 -177.55(19) . . . . ?
C12 C8 C9 N1 1.7(3) . . . . ?
C7 C8 C9 C4 2.2(3) . . . . ?
C12 C8 C9 C4 -178.5(2) . . . . ?
N3 N2 C10 C2 -177.5(2) . . . . ?
C3 C2 C10 N2 5.7(3) . . . . ?
C1 C2 C10 N2 -176.8(2) . . . . ?
C13 N4 C11 N3 178.4(2) . . . . ?
C13 N4 C11 S1 0.3(3) . . . . ?
N2 N3 C11 N4 -1.3(3) . . . . ?
N2 N3 C11 S1 176.86(16) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
N1 H1N O1 0.87(3) 1.98(3) 2.833(3) 166(3) 3_656
N3 H3N S1 0.95(3) 2.43(3) 3.373(2) 174(2) 3_566
C13 H13C S1 0.98 2.83 3.766(3) 159.8 3_576

_refine_diff_density_max         0.510
_refine_diff_density_min         -0.422
_refine_diff_density_rms         0.067

####################################################################### 
# 
# 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_6MMCN_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 1856541'
loop_
_audit_author_name
_audit_author_address
'Frank R. Fronczek'
;Department of Chemistry, Louisiana State University, Baton Rouge, LA 70803, USA
United States of America
;
_audit_update_record             
;
2018-07-18 deposited with the CCDC.	2020-02-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H18 Cu N5 O5 S, N O3'
_chemical_formula_sum            'C14 H18 Cu N6 O8 S'
_chemical_formula_weight         493.94

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'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   6.5577(2)
_cell_length_b                   10.1582(4)
_cell_length_c                   14.2821(5)
_cell_angle_alpha                82.6599(17)
_cell_angle_beta                 86.6623(18)
_cell_angle_gamma                84.3737(19)
_cell_volume                     938.05(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    90.0(5)
_cell_measurement_reflns_used    9158
_cell_measurement_theta_min      3.12
_cell_measurement_theta_max      40.30

_exptl_crystal_description       prism
_exptl_crystal_colour            greenish-blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.749
_exptl_crystal_F_000             506
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.330
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.210
_exptl_absorpt_coefficient_mu    1.335
_shelx_estimated_absorpt_T_min   0.667
_shelx_estimated_absorpt_T_max   0.767
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.713
_exptl_absorpt_correction_T_max  0.767
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2004)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      90.0(5)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  'TRIUMPH curved graphite'
_diffrn_measurement_device_type  'Bruker Kappa APEX-II DUO'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            31613
_diffrn_reflns_av_unetI/netI     0.0258
_diffrn_reflns_av_R_equivalents  0.0238
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_l_min       -25
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.030
_diffrn_reflns_theta_max         40.296
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             11780
_reflns_number_gt                10775
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0306P)²+0.2025P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         11780
_refine_ls_number_parameters     288
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0259
_refine_ls_R_factor_gt           0.0225
_refine_ls_wR_factor_ref         0.0636
_refine_ls_wR_factor_gt          0.0621
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.002
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.31729(2) 0.60996(2) 0.63745(2) 0.00844(2) Uani 1 1 d . . . . .
S1 S 0.34264(3) 0.59632(2) 0.79575(2) 0.01131(3) Uani 1 1 d . . . . .
O1 O 0.28750(9) 0.62548(5) 0.50424(3) 0.01260(8) Uani 1 1 d . . . . .
O2 O 0.26838(9) 0.42311(5) 0.63854(3) 0.01299(8) Uani 1 1 d . . . . .
H21 H 0.308(2) 0.3653(14) 0.6822(10) 0.019 Uiso 1 1 d . U . . .
H22 H 0.280(2) 0.3858(14) 0.5881(10) 0.019 Uiso 1 1 d . U . . .
O3 O 0.69043(8) 0.57242(5) 0.62636(4) 0.01368(8) Uani 1 1 d . . . . .
O4 O 0.75393(10) 0.72672(6) 0.51064(4) 0.01744(9) Uani 1 1 d . . . . .
O5 O 0.93370(9) 0.69996(6) 0.63572(5) 0.01927(10) Uani 1 1 d . . . . .
N1 N 0.20039(8) 0.71290(5) 0.35981(3) 0.00896(7) Uani 1 1 d D . . . .
H1N H 0.2063(18) 0.6330(11) 0.3521(8) 0.011 Uiso 1 1 d D U . . .
N2 N 0.33721(8) 0.80387(5) 0.63312(3) 0.00828(7) Uani 1 1 d . . . . .
N3 N 0.39213(9) 0.84532(5) 0.71487(4) 0.00987(8) Uani 1 1 d D . . . .
H3N H 0.3921(18) 0.9259(11) 0.7162(8) 0.012 Uiso 1 1 d D U . . .
N4 N 0.44445(10) 0.80452(6) 0.87217(4) 0.01235(9) Uani 1 1 d D . . . .
H4N H 0.4596(19) 0.8831(11) 0.8659(9) 0.015 Uiso 1 1 d D U . . .
N5 N 0.79381(8) 0.66573(6) 0.59082(4) 0.01098(8) Uani 1 1 d . . . . .
C1 C 0.24583(9) 0.72912(6) 0.44853(4) 0.00862(8) Uani 1 1 d . . . . .
C2 C 0.24462(9) 0.86477(6) 0.47064(4) 0.00833(8) Uani 1 1 d . . . . .
C3 C 0.19179(9) 0.96841(6) 0.40215(4) 0.00902(8) Uani 1 1 d . . . . .
H3 H 0.1899 1.0573 0.4166 0.011 Uiso 1 1 calc R U . . .
C4 C 0.13988(9) 0.94658(6) 0.31031(4) 0.00898(8) Uani 1 1 d . . . . .
C5 C 0.08677(10) 1.05260(6) 0.23900(4) 0.01123(9) Uani 1 1 d . . . . .
H5 H 0.0835 1.1425 0.2514 0.013 Uiso 1 1 calc R U . . .
C6 C 0.03996(11) 1.02400(7) 0.15156(4) 0.01321(10) Uani 1 1 d . . . . .
H6 H 0.0022 1.0946 0.1037 0.016 Uiso 1 1 calc R U . . .
C7 C 0.04755(10) 0.89114(7) 0.13259(4) 0.01232(9) Uani 1 1 d . . . . .
H7 H 0.0146 0.8741 0.0716 0.015 Uiso 1 1 calc R U . . .
C8 C 0.10127(9) 0.78419(6) 0.19960(4) 0.00967(8) Uani 1 1 d . . . . .
C9 C 0.14610(9) 0.81417(6) 0.28962(4) 0.00856(8) Uani 1 1 d . . . . .
C10 C 0.29817(9) 0.89422(6) 0.56236(4) 0.00868(8) Uani 1 1 d . . . . .
H10 H 0.3050 0.9848 0.5710 0.010 Uiso 1 1 calc R U . . .
C11 C 0.39738(9) 0.75695(6) 0.79511(4) 0.00929(8) Uani 1 1 d . . . . .
C12 C 0.11682(10) 0.64267(7) 0.17775(4) 0.01249(9) Uani 1 1 d . . . . .
H12A H 0.0647 0.6405 0.1151 0.019 Uiso 1 1 calc R U . . .
H12B H 0.0353 0.5895 0.2253 0.019 Uiso 1 1 calc R U . . .
H12C H 0.2606 0.6058 0.1786 0.019 Uiso 1 1 calc R U . . .
C13 C 0.47510(12) 0.72305(7) 0.96338(4) 0.01556(11) Uani 1 1 d . . . . .
H13A H 0.3763 0.6543 0.9725 0.019 Uiso 1 1 calc R U . . .
H13B H 0.4474 0.7802 1.0147 0.019 Uiso 1 1 calc R U . . .
C14 C 0.69203(15) 0.65548(9) 0.96964(6) 0.02228(14) Uani 1 1 d . . . . .
H14A H 0.7216 0.6011 0.9177 0.033 Uiso 1 1 calc R U . . .
H14B H 0.7047 0.5984 1.0301 0.033 Uiso 1 1 calc R U . . .
H14C H 0.7897 0.7234 0.9652 0.033 Uiso 1 1 calc R U . . .
N6 N 0.40543(8) 0.15944(5) 0.79600(4) 0.00974(7) Uani 1 1 d . . . . .
O6 O 0.39177(9) 0.28218(5) 0.80010(4) 0.01377(8) Uani 1 1 d . . . . .
O7 O 0.37807(8) 0.11776(5) 0.71845(3) 0.01239(8) Uani 1 1 d . . . . .
O8 O 0.44584(9) 0.07994(5) 0.86800(4) 0.01462(8) Uani 1 1 d . . . . .


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O1 1.9087(5) . ?
Cu1 O2 1.9537(5) . ?
Cu1 N2 1.9797(5) . ?
Cu1 S1 2.26220(18) . ?
Cu1 O3 2.4383(5) . ?
S1 C11 1.7036(6) . ?
O1 C1 1.2534(7) . ?
O2 H21 0.833(14) . ?
O2 H22 0.852(14) . ?
O3 N5 1.2565(8) . ?
O4 N5 1.2591(8) . ?
O5 N5 1.2497(8) . ?
N1 C1 1.3523(7) . ?
N1 C9 1.3770(8) . ?
N1 H1N 0.830(11) . ?
N2 C10 1.2947(8) . ?
N2 N3 1.3691(7) . ?
N3 C11 1.3623(8) . ?
N3 H3N 0.821(11) . ?
N4 C11 1.3210(8) . ?
N4 C13 1.4644(9) . ?
N4 H4N 0.807(11) . ?
C1 C2 1.4517(8) . ?
C2 C3 1.3747(8) . ?
C2 C10 1.4502(8) . ?
C3 C4 1.4237(8) . ?
C3 H3 0.9500 . ?
C4 C9 1.4097(9) . ?
C4 C5 1.4162(8) . ?
C5 C6 1.3760(9) . ?
C5 H5 0.9500 . ?
C6 C7 1.4057(10) . ?
C6 H6 0.9500 . ?
C7 C8 1.3853(9) . ?
C7 H7 0.9500 . ?
C8 C9 1.4121(8) . ?
C8 C12 1.5022(9) . ?
C10 H10 0.9500 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C14 1.5201(12) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
N6 O8 1.2480(7) . ?
N6 O6 1.2499(7) . ?
N6 O7 1.2633(7) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Cu1 O2 85.97(2) . . ?
O1 Cu1 N2 91.93(2) . . ?
O2 Cu1 N2 174.15(2) . . ?
O1 Cu1 S1 178.031(17) . . ?
O2 Cu1 S1 94.832(15) . . ?
N2 Cu1 S1 87.106(15) . . ?
O1 Cu1 O3 94.58(2) . . ?
O2 Cu1 O3 95.59(2) . . ?
N2 Cu1 O3 90.01(2) . . ?
S1 Cu1 O3 87.138(14) . . ?
C11 S1 Cu1 95.26(2) . . ?
C1 O1 Cu1 128.10(4) . . ?
Cu1 O2 H21 121.4(9) . . ?
Cu1 O2 H22 121.5(9) . . ?
H21 O2 H22 106.8(13) . . ?
N5 O3 Cu1 119.46(4) . . ?
C1 N1 C9 125.47(5) . . ?
C1 N1 H1N 111.9(8) . . ?
C9 N1 H1N 122.7(8) . . ?
C10 N2 N3 117.55(5) . . ?
C10 N2 Cu1 126.67(4) . . ?
N3 N2 Cu1 115.75(4) . . ?
C11 N3 N2 118.72(5) . . ?
C11 N3 H3N 121.9(8) . . ?
N2 N3 H3N 117.5(8) . . ?
C11 N4 C13 123.97(6) . . ?
C11 N4 H4N 115.5(9) . . ?
C13 N4 H4N 120.5(9) . . ?
O5 N5 O3 120.10(6) . . ?
O5 N5 O4 119.85(6) . . ?
O3 N5 O4 120.04(6) . . ?
O1 C1 N1 117.02(5) . . ?
O1 C1 C2 125.70(5) . . ?
N1 C1 C2 117.27(5) . . ?
C3 C2 C10 119.10(5) . . ?
C3 C2 C1 118.80(5) . . ?
C10 C2 C1 122.10(5) . . ?
C2 C3 C4 122.00(5) . . ?
C2 C3 H3 119.0 . . ?
C4 C3 H3 119.0 . . ?
C9 C4 C5 119.19(5) . . ?
C9 C4 C3 118.33(5) . . ?
C5 C4 C3 122.46(5) . . ?
C6 C5 C4 119.27(6) . . ?
C6 C5 H5 120.4 . . ?
C4 C5 H5 120.4 . . ?
C5 C6 C7 120.48(6) . . ?
C5 C6 H6 119.8 . . ?
C7 C6 H6 119.8 . . ?
C8 C7 C6 122.36(6) . . ?
C8 C7 H7 118.8 . . ?
C6 C7 H7 118.8 . . ?
C7 C8 C9 116.87(6) . . ?
C7 C8 C12 122.09(5) . . ?
C9 C8 C12 121.03(5) . . ?
N1 C9 C4 118.09(5) . . ?
N1 C9 C8 120.09(5) . . ?
C4 C9 C8 121.82(5) . . ?
N2 C10 C2 123.65(5) . . ?
N2 C10 H10 118.2 . . ?
C2 C10 H10 118.2 . . ?
N4 C11 N3 115.69(5) . . ?
N4 C11 S1 122.44(5) . . ?
N3 C11 S1 121.86(4) . . ?
C8 C12 H12A 109.5 . . ?
C8 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C8 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
N4 C13 C14 111.80(6) . . ?
N4 C13 H13A 109.3 . . ?
C14 C13 H13A 109.3 . . ?
N4 C13 H13B 109.3 . . ?
C14 C13 H13B 109.3 . . ?
H13A C13 H13B 107.9 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
O8 N6 O6 119.91(5) . . ?
O8 N6 O7 120.94(5) . . ?
O6 N6 O7 119.16(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
C10 N2 N3 C11 168.11(6) . . . . ?
Cu1 N2 N3 C11 -9.98(7) . . . . ?
Cu1 O3 N5 O5 126.11(5) . . . . ?
Cu1 O3 N5 O4 -52.48(7) . . . . ?
Cu1 O1 C1 N1 -169.64(4) . . . . ?
Cu1 O1 C1 C2 11.17(10) . . . . ?
C9 N1 C1 O1 178.35(6) . . . . ?
C9 N1 C1 C2 -2.40(9) . . . . ?
O1 C1 C2 C3 -178.82(6) . . . . ?
N1 C1 C2 C3 2.00(8) . . . . ?
O1 C1 C2 C10 1.46(10) . . . . ?
N1 C1 C2 C10 -177.72(5) . . . . ?
C10 C2 C3 C4 179.26(5) . . . . ?
C1 C2 C3 C4 -0.47(9) . . . . ?
C2 C3 C4 C9 -0.83(9) . . . . ?
C2 C3 C4 C5 -179.50(6) . . . . ?
C9 C4 C5 C6 0.81(9) . . . . ?
C3 C4 C5 C6 179.47(6) . . . . ?
C4 C5 C6 C7 -0.92(10) . . . . ?
C5 C6 C7 C8 0.06(10) . . . . ?
C6 C7 C8 C9 0.88(9) . . . . ?
C6 C7 C8 C12 -177.63(6) . . . . ?
C1 N1 C9 C4 1.12(9) . . . . ?
C1 N1 C9 C8 -179.74(6) . . . . ?
C5 C4 C9 N1 179.29(6) . . . . ?
C3 C4 C9 N1 0.57(8) . . . . ?
C5 C4 C9 C8 0.15(9) . . . . ?
C3 C4 C9 C8 -178.56(6) . . . . ?
C7 C8 C9 N1 179.91(6) . . . . ?
C12 C8 C9 N1 -1.56(9) . . . . ?
C7 C8 C9 C4 -0.97(9) . . . . ?
C12 C8 C9 C4 177.55(6) . . . . ?
N3 N2 C10 C2 177.98(5) . . . . ?
Cu1 N2 C10 C2 -4.16(9) . . . . ?
C3 C2 C10 N2 175.43(6) . . . . ?
C1 C2 C10 N2 -4.85(9) . . . . ?
C13 N4 C11 N3 -174.58(6) . . . . ?
C13 N4 C11 S1 6.40(10) . . . . ?
N2 N3 C11 N4 -177.70(6) . . . . ?
N2 N3 C11 S1 1.32(8) . . . . ?
Cu1 S1 C11 N4 -174.81(5) . . . . ?
Cu1 S1 C11 N3 6.23(5) . . . . ?
C11 N4 C13 C14 83.97(8) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H21 N6 0.833(14) 2.533(14) 3.3561(7) 169.4(13) .
O2 H21 O6 0.833(14) 1.873(14) 2.6785(7) 162.2(14) .
O2 H21 O7 0.833(14) 2.505(14) 3.1929(7) 140.6(12) .
O2 H22 O4 0.852(14) 1.960(14) 2.7902(7) 164.3(13) 2_666
N1 H1N O3 0.830(11) 2.119(11) 2.9008(7) 156.9(11) 2_666
N3 H3N O7 0.821(11) 1.946(11) 2.7670(7) 177.3(12) 1_565
N4 H4N O8 0.807(11) 1.997(11) 2.7917(8) 168.3(13) 1_565
C13 H13B O8 0.99 2.50 3.4138(8) 153.2 2_667
C14 H14B S1 0.98 2.99 3.9568(8) 167.5 2_667

_refine_diff_density_max         0.688
_refine_diff_density_min         -0.523
_refine_diff_density_rms         0.073

####################################################################### 
# 
# 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_6MPCN
_database_code_depnum_ccdc_archive 'CCDC 1856542'
loop_
_audit_author_name
_audit_author_address
'Frank R. Fronczek'
;Department of Chemistry, Louisiana State University, Baton Rouge, LA 70803, USA
United States of America
;
_audit_update_record             
;
2018-07-18 deposited with the CCDC.	2020-02-26 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014/7
_shelx_SHELXL_version_number     2014/7
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C18 H17 Cu N4 O2 S, N O3'
_chemical_formula_sum            'C18 H17 Cu N5 O5 S'
_chemical_formula_weight         519.02

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'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_H-M_alt        'I 2/a'
_space_group_name_Hall           '-I 2ya'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'

_cell_length_a                   17.4083(9)
_cell_length_b                   11.2925(5)
_cell_length_c                   22.1298(16)
_cell_angle_alpha                90
_cell_angle_beta                 99.164(2)
_cell_angle_gamma                90
_cell_volume                     4294.8(4)
_cell_formula_units_Z            8
_cell_measurement_temperature    90.0(5)
_cell_measurement_reflns_used    9008
_cell_measurement_theta_min      2.73
_cell_measurement_theta_max      30.98

_exptl_crystal_description       prism
_exptl_crystal_colour            'dark green'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.605
_exptl_crystal_F_000             2140
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.370
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.080
_exptl_absorpt_coefficient_mu    1.164
_shelx_estimated_absorpt_T_min   0.673
_shelx_estimated_absorpt_T_max   0.913
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.831
_exptl_absorpt_correction_T_max  0.913
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2004)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      90.0(5)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  'TRIUMPH curved graphite'
_diffrn_measurement_device_type  'Bruker Kappa APEX-II DUO'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_reflns_number            22733
_diffrn_reflns_av_unetI/netI     0.0269
_diffrn_reflns_av_R_equivalents  0.0250
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       25
_diffrn_reflns_limit_k_min       -16
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         2.030
_diffrn_reflns_theta_max         31.009
_diffrn_reflns_theta_full        25.000
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             6771
_reflns_number_gt                5691
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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.
;

_computing_data_collection       'Bruker APEX3'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    ?
_computing_publication_material  ?
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0438P)²+9.3125P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         6771
_refine_ls_number_parameters     309
_refine_ls_number_restraints     34
_refine_ls_R_factor_all          0.0457
_refine_ls_R_factor_gt           0.0368
_refine_ls_wR_factor_ref         0.0994
_refine_ls_wR_factor_gt          0.0951
_refine_ls_goodness_of_fit_ref   1.057
_refine_ls_restrained_S_all      1.057
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.64987(2) 0.24297(2) 0.47950(2) 0.01449(6) Uani 1 1 d . . . . .
S1 S 0.72696(2) 0.18574(4) 0.41261(2) 0.01611(9) Uani 1 1 d . . . . .
O1 O 0.58887(7) 0.29668(11) 0.54096(6) 0.0162(2) Uani 1 1 d . . . . .
O2 O 0.60373(9) 0.08811(13) 0.48993(7) 0.0234(3) Uani 1 1 d D . . . .
H21 H 0.5877(16) 0.069(2) 0.5220(9) 0.035 Uiso 1 1 d D U . . .
H22 H 0.6162(16) 0.0243(18) 0.4766(11) 0.035 Uiso 1 1 d D U . . .
N1 N 0.53349(8) 0.41992(14) 0.60096(7) 0.0156(3) Uani 1 1 d D . . . .
H1N H 0.5199(13) 0.3598(19) 0.6181(11) 0.019 Uiso 1 1 d D U . . .
N2 N 0.67072(8) 0.40488(13) 0.45441(6) 0.0137(3) Uani 1 1 d . . . . .
N3 N 0.71229(8) 0.42563(13) 0.40729(7) 0.0147(3) Uani 1 1 d . . . . .
N4 N 0.77697(8) 0.33625(13) 0.33638(7) 0.0154(3) Uani 1 1 d D . . . .
H4N H 0.7936(14) 0.2723(19) 0.3281(11) 0.018 Uiso 1 1 d D U . . .
C1 C 0.57604(9) 0.40264(15) 0.55545(8) 0.0144(3) Uani 1 1 d . . . . .
C2 C 0.60205(9) 0.50695(15) 0.52687(8) 0.0145(3) Uani 1 1 d . . . . .
C3 C 0.58175(10) 0.61673(16) 0.54598(8) 0.0162(3) Uani 1 1 d . . . . .
H3 H 0.5982 0.6852 0.5266 0.019 Uiso 1 1 calc R U . . .
C4 C 0.53702(10) 0.63103(16) 0.59364(8) 0.0169(3) Uani 1 1 d . . . . .
C5 C 0.51700(10) 0.74423(17) 0.61356(9) 0.0200(3) Uani 1 1 d . . . . .
H5 H 0.5327 0.8138 0.5946 0.024 Uiso 1 1 calc R U . . .
C6 C 0.47451(11) 0.75221(19) 0.66074(9) 0.0239(4) Uani 1 1 d . . . . .
H6 H 0.4613 0.8278 0.6749 0.029 Uiso 1 1 calc R U . . .
C7 C 0.45055(11) 0.64960(19) 0.68799(9) 0.0231(4) Uani 1 1 d . . . . .
H7 H 0.4212 0.6577 0.7205 0.028 Uiso 1 1 calc R U . . .
C8 C 0.46786(10) 0.53682(18) 0.66957(8) 0.0200(3) Uani 1 1 d . . . . .
C9 C 0.51291(9) 0.52944(16) 0.62178(8) 0.0160(3) Uani 1 1 d . . . . .
C10 C 0.64742(9) 0.50120(15) 0.47787(8) 0.0148(3) Uani 1 1 d . . . . .
H10 H 0.6615 0.5742 0.4613 0.018 Uiso 1 1 calc R U . . .
C11 C 0.73792(9) 0.32924(15) 0.38491(8) 0.0139(3) Uani 1 1 d . . . . .
C12 C 0.43878(11) 0.4282(2) 0.69761(9) 0.0256(4) Uani 1 1 d . . . . .
H12A H 0.4138 0.4510 0.7325 0.038 Uiso 1 1 calc R U . . .
H12B H 0.4826 0.3751 0.7115 0.038 Uiso 1 1 calc R U . . .
H12C H 0.4010 0.3874 0.6671 0.038 Uiso 1 1 calc R U . . .
C13 C 0.79835(9) 0.43589(15) 0.30425(8) 0.0147(3) Uani 1 1 d . . . . .
C14 C 0.78845(10) 0.55380(16) 0.32115(8) 0.0161(3) Uani 1 1 d . . . . .
H14 H 0.7636 0.5715 0.3553 0.019 Uiso 1 1 calc R U . . .
C15 C 0.81522(10) 0.64468(16) 0.28765(8) 0.0181(3) Uani 1 1 d . . . . .
H15 H 0.8089 0.7245 0.2995 0.022 Uiso 1 1 calc R U . . .
C16 C 0.85085(11) 0.62142(17) 0.23734(9) 0.0209(3) Uani 1 1 d . . . . .
H16 H 0.8693 0.6845 0.2151 0.025 Uiso 1 1 calc R U . . .
C17 C 0.85940(11) 0.50419(17) 0.21969(9) 0.0210(3) Uani 1 1 d . . . . .
H17 H 0.8830 0.4872 0.1848 0.025 Uiso 1 1 calc R U . . .
C18 C 0.83356(10) 0.41235(16) 0.25297(8) 0.0179(3) Uani 1 1 d . . . . .
H18 H 0.8398 0.3327 0.2408 0.022 Uiso 1 1 calc R U . . .
N5A N 0.5701(2) 0.1122(3) 0.64528(18) 0.0261(6) Uani 0.516(4) 1 d D . P A 1
O3A O 0.5621(3) 0.0331(6) 0.6041(3) 0.0327(9) Uani 0.516(4) 1 d D . P A 1
O4A O 0.5123(2) 0.1804(3) 0.64909(16) 0.0281(7) Uani 0.516(4) 1 d D . P A 1
O5A O 0.6329(2) 0.1203(3) 0.68209(16) 0.0328(8) Uani 0.516(4) 1 d D . P A 1
N5B N 0.5320(3) 0.1353(4) 0.6303(2) 0.0261(6) Uani 0.484(4) 1 d D . P A 2
O3B O 0.5349(3) 0.0446(6) 0.5974(4) 0.0327(9) Uani 0.484(4) 1 d D . P A 2
O4B O 0.4716(2) 0.1969(3) 0.6234(2) 0.0322(8) Uani 0.484(4) 1 d D . P A 2
O5B O 0.5908(3) 0.1648(4) 0.66833(17) 0.0392(11) Uani 0.484(4) 1 d D . P A 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O1 1.9507(13) . ?
Cu1 O2 1.9533(14) . ?
Cu1 N2 1.9614(15) . ?
Cu1 S1 2.2454(5) . ?
S1 C11 1.7536(18) . ?
O1 C1 1.268(2) . ?
O2 H21 0.831(16) . ?
O2 H22 0.821(16) . ?
N1 C1 1.356(2) . ?
N1 C9 1.387(2) . ?
N1 H1N 0.83(2) . ?
N2 C10 1.298(2) . ?
N2 N3 1.381(2) . ?
N3 C11 1.304(2) . ?
N4 C11 1.362(2) . ?
N4 C13 1.412(2) . ?
N4 H4N 0.81(2) . ?
C1 C2 1.443(2) . ?
C2 C3 1.374(2) . ?
C2 C10 1.441(2) . ?
C3 C4 1.416(2) . ?
C3 H3 0.9500 . ?
C4 C9 1.401(3) . ?
C4 C5 1.414(2) . ?
C5 C6 1.375(3) . ?
C5 H5 0.9500 . ?
C6 C7 1.400(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.385(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.416(2) . ?
C8 C12 1.499(3) . ?
C10 H10 0.9500 . ?
C12 H12A 0.9800 . ?
C12 H12B 0.9800 . ?
C12 H12C 0.9800 . ?
C13 C18 1.399(2) . ?
C13 C14 1.401(2) . ?
C14 C15 1.389(3) . ?
C14 H14 0.9500 . ?
C15 C16 1.383(3) . ?
C15 H15 0.9500 . ?
C16 C17 1.395(3) . ?
C16 H16 0.9500 . ?
C17 C18 1.388(3) . ?
C17 H17 0.9500 . ?
C18 H18 0.9500 . ?
N5A O5A 1.258(5) . ?
N5A O3A 1.267(6) . ?
N5A O4A 1.281(5) . ?
N5B O4B 1.249(5) . ?
N5B O5B 1.261(5) . ?
N5B O3B 1.262(7) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Cu1 O2 85.19(6) . . ?
O1 Cu1 N2 93.06(6) . . ?
O2 Cu1 N2 165.03(6) . . ?
O1 Cu1 S1 176.30(4) . . ?
O2 Cu1 S1 96.92(4) . . ?
N2 Cu1 S1 85.68(4) . . ?
C11 S1 Cu1 94.26(6) . . ?
C1 O1 Cu1 127.39(11) . . ?
Cu1 O2 H21 122.0(19) . . ?
Cu1 O2 H22 127.3(19) . . ?
H21 O2 H22 103(2) . . ?
C1 N1 C9 125.15(16) . . ?
C1 N1 H1N 116.8(17) . . ?
C9 N1 H1N 118.0(17) . . ?
C10 N2 N3 113.24(15) . . ?
C10 N2 Cu1 125.76(12) . . ?
N3 N2 Cu1 120.99(11) . . ?
C11 N3 N2 113.42(14) . . ?
C11 N4 C13 130.40(15) . . ?
C11 N4 H4N 111.6(18) . . ?
C13 N4 H4N 117.7(18) . . ?
O1 C1 N1 117.57(16) . . ?
O1 C1 C2 125.40(15) . . ?
N1 C1 C2 117.03(15) . . ?
C3 C2 C10 118.09(16) . . ?
C3 C2 C1 119.17(15) . . ?
C10 C2 C1 122.72(15) . . ?
C2 C3 C4 122.06(17) . . ?
C2 C3 H3 119.0 . . ?
C4 C3 H3 119.0 . . ?
C9 C4 C5 119.70(16) . . ?
C9 C4 C3 118.47(16) . . ?
C5 C4 C3 121.83(17) . . ?
C6 C5 C4 119.02(18) . . ?
C6 C5 H5 120.5 . . ?
C4 C5 H5 120.5 . . ?
C5 C6 C7 120.39(18) . . ?
C5 C6 H6 119.8 . . ?
C7 C6 H6 119.8 . . ?
C8 C7 C6 122.71(17) . . ?
C8 C7 H7 118.6 . . ?
C6 C7 H7 118.6 . . ?
C7 C8 C9 116.52(18) . . ?
C7 C8 C12 121.81(17) . . ?
C9 C8 C12 121.66(17) . . ?
N1 C9 C4 118.10(15) . . ?
N1 C9 C8 120.26(17) . . ?
C4 C9 C8 121.64(17) . . ?
N2 C10 C2 125.62(16) . . ?
N2 C10 H10 117.2 . . ?
C2 C10 H10 117.2 . . ?
N3 C11 N4 119.68(16) . . ?
N3 C11 S1 125.16(13) . . ?
N4 C11 S1 115.16(12) . . ?
C8 C12 H12A 109.5 . . ?
C8 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
C8 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C18 C13 C14 119.06(16) . . ?
C18 C13 N4 116.22(15) . . ?
C14 C13 N4 124.70(15) . . ?
C15 C14 C13 119.57(16) . . ?
C15 C14 H14 120.2 . . ?
C13 C14 H14 120.2 . . ?
C16 C15 C14 121.39(17) . . ?
C16 C15 H15 119.3 . . ?
C14 C15 H15 119.3 . . ?
C15 C16 C17 119.16(17) . . ?
C15 C16 H16 120.4 . . ?
C17 C16 H16 120.4 . . ?
C18 C17 C16 120.17(17) . . ?
C18 C17 H17 119.9 . . ?
C16 C17 H17 119.9 . . ?
C17 C18 C13 120.63(17) . . ?
C17 C18 H18 119.7 . . ?
C13 C18 H18 119.7 . . ?
O5A N5A O3A 120.1(4) . . ?
O5A N5A O4A 121.6(4) . . ?
O3A N5A O4A 118.3(4) . . ?
O4B N5B O5B 120.8(5) . . ?
O4B N5B O3B 119.4(4) . . ?
O5B N5B O3B 119.8(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
C10 N2 N3 C11 177.93(15) . . . . ?
Cu1 N2 N3 C11 -3.14(18) . . . . ?
Cu1 O1 C1 N1 -178.21(11) . . . . ?
Cu1 O1 C1 C2 2.8(2) . . . . ?
C9 N1 C1 O1 -178.80(15) . . . . ?
C9 N1 C1 C2 0.3(2) . . . . ?
O1 C1 C2 C3 177.93(16) . . . . ?
N1 C1 C2 C3 -1.1(2) . . . . ?
O1 C1 C2 C10 -0.7(3) . . . . ?
N1 C1 C2 C10 -179.77(14) . . . . ?
C10 C2 C3 C4 179.75(15) . . . . ?
C1 C2 C3 C4 1.0(2) . . . . ?
C2 C3 C4 C9 -0.1(3) . . . . ?
C2 C3 C4 C5 179.31(16) . . . . ?
C9 C4 C5 C6 0.5(3) . . . . ?
C3 C4 C5 C6 -178.94(17) . . . . ?
C4 C5 C6 C7 -0.9(3) . . . . ?
C5 C6 C7 C8 0.1(3) . . . . ?
C6 C7 C8 C9 1.1(3) . . . . ?
C6 C7 C8 C12 -177.39(18) . . . . ?
C1 N1 C9 C4 0.6(2) . . . . ?
C1 N1 C9 C8 179.70(15) . . . . ?
C5 C4 C9 N1 179.88(15) . . . . ?
C3 C4 C9 N1 -0.7(2) . . . . ?
C5 C4 C9 C8 0.8(3) . . . . ?
C3 C4 C9 C8 -179.79(15) . . . . ?
C7 C8 C9 N1 179.38(16) . . . . ?
C12 C8 C9 N1 -2.1(3) . . . . ?
C7 C8 C9 C4 -1.5(3) . . . . ?
C12 C8 C9 C4 176.97(16) . . . . ?
N3 N2 C10 C2 179.06(15) . . . . ?
Cu1 N2 C10 C2 0.2(2) . . . . ?
C3 C2 C10 N2 -179.52(16) . . . . ?
C1 C2 C10 N2 -0.8(3) . . . . ?
N2 N3 C11 N4 177.12(14) . . . . ?
N2 N3 C11 S1 -3.2(2) . . . . ?
C13 N4 C11 N3 2.0(3) . . . . ?
C13 N4 C11 S1 -177.69(14) . . . . ?
Cu1 S1 C11 N3 6.48(15) . . . . ?
Cu1 S1 C11 N4 -173.85(12) . . . . ?
C11 N4 C13 C18 -175.35(17) . . . . ?
C11 N4 C13 C14 6.3(3) . . . . ?
C18 C13 C14 C15 -1.4(2) . . . . ?
N4 C13 C14 C15 176.85(16) . . . . ?
C13 C14 C15 C16 0.7(3) . . . . ?
C14 C15 C16 C17 0.5(3) . . . . ?
C15 C16 C17 C18 -1.1(3) . . . . ?
C16 C17 C18 C13 0.4(3) . . . . ?
C14 C13 C18 C17 0.9(3) . . . . ?
N4 C13 C18 C17 -177.52(16) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H21 O3A 0.831(16) 1.981(18) 2.807(8) 173(3) .
O2 H21 O3B 0.831(16) 2.049(18) 2.871(9) 170(3) .
N1 H1N O4A 0.83(2) 2.15(2) 2.951(3) 162(2) .
N1 H1N N5B 0.83(2) 2.55(2) 3.279(4) 147(2) .
N1 H1N O4B 0.83(2) 2.03(2) 2.814(4) 156(2) .
N4 H4N O5A 0.81(2) 2.17(2) 2.963(3) 165(2) 2_656
N4 H4N O5B 0.81(2) 2.34(2) 3.023(4) 142(2) 2_656
C14 H14 N3 0.95 2.27 2.880(2) 121.1 .

_refine_diff_density_max         1.000
_refine_diff_density_min         -0.398
_refine_diff_density_rms         0.087

# SQUEEZE RESULTS (APPEND TO CIF)
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.250 0.152 0.500 134 47 ' '
2 0.250 0.348 0.000 134 47 ' '
3 0.750 0.652 0.000 134 47 ' '
4 0.750 0.848 0.500 134 47 ' '
_platon_squeeze_details          
;
The 188 electrons removed by SQUEEZE correspond approximately
to 10 molecules of disordered methanol per unit cell. This
solvent is included in the FW, density, mu value, etc., but
is not in the formula nor model.
;

