# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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 2031938'
loop_
_audit_author_name
_audit_author_address
'Martin Zabransky'
;Department of Inorganic Chemistry, Faculty of Science, Charles University, Prague
Czech Republic
;
_audit_update_record             
;
2020-09-14 deposited with the CCDC.	2020-12-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H18 N5 O3, C10 H15 O4 S'
_chemical_formula_sum            'C24 H33 N5 O7 S'
_chemical_formula_weight         535.61

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'
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'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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+1/2, -z'
'-x, y+1/2, -z+1/2'
'-x+1/2, -y, z+1/2'

_cell_length_a                   6.7041(8)
_cell_length_b                   11.8458(10)
_cell_length_c                   30.358(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2410.9(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    993
_cell_measurement_theta_min      3.11
_cell_measurement_theta_max      21.97

_exptl_crystal_description       plate
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.476
_exptl_crystal_F_000             1136
_exptl_transmission_factor_min   0.640
_exptl_transmission_factor_max   0.640
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.04
_exptl_absorpt_coefficient_mu    0.191
_shelx_estimated_absorpt_T_min   0.986
_shelx_estimated_absorpt_T_max   0.992
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.852
_exptl_absorpt_correction_T_max  0.992
_exptl_absorpt_process_details   'SADABS (Bruker,2005)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            10172
_diffrn_reflns_av_unetI/netI     0.1204
_diffrn_reflns_av_R_equivalents  0.0720
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_theta_min         3.112
_diffrn_reflns_theta_max         25.457
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             4452
_reflns_number_gt                2947
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.726
_reflns_Friedel_fraction_max     0.994
_reflns_Friedel_fraction_full    1.000

_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-2013/1 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'PLATON (Spek, 2016)'
_computing_publication_material  'PLATON (Spek, 2016)'
_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)+(0.0435P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 877 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.11(11)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         4452
_refine_ls_number_parameters     346
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1070
_refine_ls_R_factor_gt           0.0569
_refine_ls_wR_factor_ref         0.1164
_refine_ls_wR_factor_gt          0.1036
_refine_ls_goodness_of_fit_ref   0.952
_refine_ls_restrained_S_all      0.952
_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
C1 C 0.6960(8) 0.2078(4) 1.0350(2) 0.0138(13) Uani 1 1 d . . . . .
C2 C 0.7092(8) 0.1043(4) 1.01042(19) 0.0151(12) Uani 1 1 d . . . . .
C3 C 0.7289(7) 0.1073(4) 0.96621(19) 0.0161(13) Uani 1 1 d . . . . .
H3 H 0.740665 0.038750 0.951507 0.019 Uiso 1 1 calc R U . . .
C4 C 0.7056(8) 0.4977(4) 0.95997(19) 0.0152(14) Uani 1 1 d . . . . .
C5 C 0.7031(8) 0.4179(4) 1.02774(19) 0.0144(13) Uani 1 1 d . . . . .
H5 H 0.701018 0.424162 1.058272 0.017 Uiso 1 1 calc R U . . .
C6 C 0.7048(8) 0.3091(4) 1.00936(19) 0.0136(13) Uani 1 1 d . . . . .
C7 C 0.7150(8) 0.3063(4) 0.96322(19) 0.0131(13) Uani 1 1 d . . . . .
C8 C 0.7038(9) -0.0080(5) 1.0326(2) 0.0159(13) Uani 1 1 d . . . . .
C9 C 0.7539(8) 0.1967(4) 0.89356(19) 0.0183(14) Uani 1 1 d . . . . .
H6 H 0.834285 0.131479 0.885983 0.022 Uiso 1 1 calc R U . . .
H7 H 0.823623 0.263501 0.883336 0.022 Uiso 1 1 calc R U . . .
C10 C 0.5574(10) 0.1886(6) 0.8704(2) 0.0415(18) Uani 1 1 d . . . . .
H8 H 0.579281 0.185037 0.839132 0.062 Uiso 1 1 calc R U . . .
H9 H 0.488845 0.121732 0.879846 0.062 Uiso 1 1 calc R U . . .
H10 H 0.478183 0.253761 0.877199 0.062 Uiso 1 1 calc R U . . .
C11 C 0.6907(9) 0.7047(4) 0.95540(19) 0.0198(14) Uani 1 1 d . . . . .
H11 H 0.815561 0.742707 0.949016 0.024 Uiso 1 1 calc R U . . .
H12 H 0.677407 0.698648 0.987130 0.024 Uiso 1 1 calc R U . . .
C12 C 0.5183(8) 0.7728(4) 0.93691(18) 0.0171(13) Uani 1 1 d . . . . .
H13 H 0.393073 0.738701 0.945811 0.021 Uiso 1 1 calc R U . . .
H14 H 0.522646 0.848903 0.948689 0.021 Uiso 1 1 calc R U . . .
C13 C 0.7004(9) 0.5926(4) 0.88793(18) 0.0208(13) Uani 1 1 d . . . . .
H15 H 0.693583 0.515669 0.877084 0.025 Uiso 1 1 calc R U . . .
H16 H 0.826129 0.624910 0.878370 0.025 Uiso 1 1 calc R U . . .
C14 C 0.5302(9) 0.6602(4) 0.86902(19) 0.0202(14) Uani 1 1 d . . . . .
H17 H 0.543674 0.664382 0.837249 0.024 Uiso 1 1 calc R U . . .
H18 H 0.404861 0.623028 0.875677 0.024 Uiso 1 1 calc R U . . .
C21 C 1.0729(9) 0.9610(4) 0.79762(18) 0.0175(14) Uani 1 1 d . . . . .
H21A H 1.027221 1.037370 0.803221 0.021 Uiso 1 1 calc R U . . .
H21B H 1.214067 0.966241 0.790905 0.021 Uiso 1 1 calc R U . . .
C22 C 0.9696(8) 0.9219(4) 0.75555(19) 0.0140(12) Uani 1 1 d . . . . .
C23 C 1.0486(9) 0.9891(4) 0.71654(19) 0.0189(13) Uani 1 1 d . . . . .
C24 C 0.9047(8) 0.9722(5) 0.6792(2) 0.0233(15) Uani 1 1 d . . . . .
H24A H 0.968542 0.935880 0.654284 0.028 Uiso 1 1 calc R U . . .
H24B H 0.846996 1.043271 0.669725 0.028 Uiso 1 1 calc R U . . .
C25 C 0.7468(8) 0.8951(4) 0.70030(18) 0.0199(13) Uani 1 1 d . . . . .
H25 H 0.617452 0.895046 0.685282 0.024 Uiso 1 1 calc R U . . .
C26 C 0.8454(9) 0.7783(4) 0.7042(2) 0.0255(15) Uani 1 1 d . . . . .
H26A H 0.905534 0.755497 0.676488 0.031 Uiso 1 1 calc R U . . .
H26B H 0.749997 0.721419 0.713324 0.031 Uiso 1 1 calc R U . . .
C27 C 1.0061(8) 0.7986(4) 0.7401(2) 0.0201(14) Uani 1 1 d . . . . .
H27A H 1.139207 0.790178 0.728017 0.024 Uiso 1 1 calc R U . . .
H27B H 0.989883 0.746113 0.764358 0.024 Uiso 1 1 calc R U . . .
C28 C 0.7397(8) 0.9347(4) 0.7486(2) 0.0195(14) Uani 1 1 d . . . . .
C29 C 0.6116(9) 0.8582(5) 0.7770(2) 0.0265(16) Uani 1 1 d . . . . .
H29A H 0.654941 0.781410 0.773565 0.040 Uiso 1 1 calc R U . . .
H29B H 0.624128 0.880093 0.807293 0.040 Uiso 1 1 calc R U . . .
H29C H 0.474728 0.864541 0.768034 0.040 Uiso 1 1 calc R U . . .
C30 C 0.6700(8) 1.0565(4) 0.7542(2) 0.0276(16) Uani 1 1 d . . . . .
H30A H 0.750706 1.105217 0.736262 0.041 Uiso 1 1 calc R U . . .
H30B H 0.533092 1.062618 0.745255 0.041 Uiso 1 1 calc R U . . .
H30C H 0.682491 1.078169 0.784515 0.041 Uiso 1 1 calc R U . . .
N1 N 0.5291(8) 0.7771(4) 0.88798(17) 0.0191(12) Uani 1 1 d . . . . .
N2 N 0.6921(7) 0.5921(3) 0.93583(15) 0.0148(10) Uani 1 1 d . . . . .
N3 N 0.7328(6) 0.2025(3) 0.94168(16) 0.0152(11) Uani 1 1 d . . . . .
N4 N 0.7136(6) 0.3982(3) 0.93812(15) 0.0153(10) Uani 1 1 d . . . . .
N5 N 0.7044(7) 0.5108(3) 1.00453(16) 0.0170(11) Uani 1 1 d . . . . .
O1 O 0.6890(6) -0.0038(3) 1.07612(14) 0.0232(10) Uani 1 1 d . . . . .
O2 O 0.7137(6) -0.0965(3) 1.01321(13) 0.0262(10) Uani 1 1 d . . . . .
O3 O 0.6781(6) 0.2091(3) 1.07618(13) 0.0176(9) Uani 1 1 d . . . . .
O21 O 0.8569(5) 0.9124(3) 0.86664(13) 0.0220(10) Uani 1 1 d . . . . .
O22 O 1.2136(6) 0.9345(3) 0.87491(14) 0.0294(11) Uani 1 1 d . . . . .
O23 O 1.0819(7) 0.7671(3) 0.83992(14) 0.0367(13) Uani 1 1 d . . . . .
O24 O 1.2028(6) 1.0436(3) 0.71535(14) 0.0265(10) Uani 1 1 d . . . . .
S1 S 1.0529(2) 0.88638(12) 0.84847(5) 0.0187(3) Uani 1 1 d . . . . .
H1 H 0.688(9) 0.076(5) 1.081(2) 0.05(2) Uiso 1 1 d . . . . .
H2 H 0.628(9) 0.811(4) 0.876(2) 0.019(17) Uiso 1 1 d . . . . .
H4 H 0.408(13) 0.812(7) 0.876(3) 0.09(3) 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
C1 O3 1.255(6) . ?
C1 C6 1.433(7) . ?
C1 C2 1.439(7) . ?
C2 C3 1.349(7) . ?
C2 C8 1.491(7) . ?
C3 N3 1.352(7) . ?
C4 N2 1.341(7) . ?
C4 N4 1.354(6) . ?
C4 N5 1.361(7) . ?
C5 N5 1.307(6) . ?
C5 C6 1.404(7) . ?
C6 C7 1.403(8) . ?
C7 N4 1.328(6) . ?
C7 N3 1.398(6) . ?
C8 O2 1.203(6) . ?
C8 O1 1.327(7) . ?
C9 N3 1.469(7) . ?
C9 C10 1.496(8) . ?
C11 N2 1.460(6) . ?
C11 C12 1.517(7) . ?
C12 N1 1.488(7) . ?
C13 N2 1.455(7) . ?
C13 C14 1.508(7) . ?
C14 N1 1.500(7) . ?
C21 C22 1.525(8) . ?
C21 S1 1.784(5) . ?
C22 C23 1.522(8) . ?
C22 C27 1.553(6) . ?
C22 C28 1.563(7) . ?
C23 O24 1.218(6) . ?
C23 C24 1.502(8) . ?
C24 C25 1.538(8) . ?
C25 C26 1.537(7) . ?
C25 C28 1.540(8) . ?
C26 C27 1.552(8) . ?
C28 C29 1.518(8) . ?
C28 C30 1.526(7) . ?
O21 S1 1.458(4) . ?
O22 S1 1.459(4) . ?
O23 S1 1.450(4) . ?

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
O3 C1 C6 122.3(5) . . ?
O3 C1 C2 122.3(5) . . ?
C6 C1 C2 115.4(5) . . ?
C3 C2 C1 120.0(5) . . ?
C3 C2 C8 118.3(5) . . ?
C1 C2 C8 121.6(5) . . ?
C2 C3 N3 124.9(5) . . ?
N2 C4 N4 117.5(5) . . ?
N2 C4 N5 116.6(5) . . ?
N4 C4 N5 125.9(5) . . ?
N5 C5 C6 123.9(5) . . ?
C7 C6 C5 114.8(5) . . ?
C7 C6 C1 121.7(5) . . ?
C5 C6 C1 123.5(5) . . ?
N4 C7 N3 116.9(5) . . ?
N4 C7 C6 123.6(5) . . ?
N3 C7 C6 119.5(4) . . ?
O2 C8 O1 121.6(5) . . ?
O2 C8 C2 123.7(6) . . ?
O1 C8 C2 114.7(5) . . ?
N3 C9 C10 112.7(5) . . ?
N2 C11 C12 109.9(5) . . ?
N1 C12 C11 110.5(5) . . ?
N2 C13 C14 110.7(5) . . ?
N1 C14 C13 110.4(5) . . ?
C22 C21 S1 122.7(4) . . ?
C23 C22 C21 109.5(4) . . ?
C23 C22 C27 101.7(4) . . ?
C21 C22 C27 117.8(4) . . ?
C23 C22 C28 100.8(4) . . ?
C21 C22 C28 122.1(5) . . ?
C27 C22 C28 101.9(4) . . ?
O24 C23 C24 126.4(5) . . ?
O24 C23 C22 126.5(5) . . ?
C24 C23 C22 107.1(5) . . ?
C23 C24 C25 102.0(5) . . ?
C26 C25 C24 105.7(5) . . ?
C26 C25 C28 102.4(4) . . ?
C24 C25 C28 103.7(4) . . ?
C25 C26 C27 102.3(4) . . ?
C26 C27 C22 104.4(4) . . ?
C29 C28 C30 109.2(5) . . ?
C29 C28 C25 112.1(4) . . ?
C30 C28 C25 113.8(5) . . ?
C29 C28 C22 115.0(5) . . ?
C30 C28 C22 112.2(4) . . ?
C25 C28 C22 93.9(4) . . ?
C12 N1 C14 110.6(4) . . ?
C4 N2 C13 123.1(4) . . ?
C4 N2 C11 122.7(5) . . ?
C13 N2 C11 113.8(4) . . ?
C3 N3 C7 118.3(5) . . ?
C3 N3 C9 120.7(4) . . ?
C7 N3 C9 121.0(4) . . ?
C7 N4 C4 115.6(5) . . ?
C5 N5 C4 116.1(5) . . ?
O23 S1 O21 113.2(3) . . ?
O23 S1 O22 112.4(3) . . ?
O21 S1 O22 112.0(2) . . ?
O23 S1 C21 108.5(3) . . ?
O21 S1 C21 106.9(3) . . ?
O22 S1 C21 103.1(3) . . ?

_refine_diff_density_max         0.295
_refine_diff_density_min         -0.389
_refine_diff_density_rms         0.069

####################################################################### 
# 
# 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_190227im_mz_mz030_water_0m
_database_code_depnum_ccdc_archive 'CCDC 2031940'
loop_
_audit_author_name
_audit_author_address
'Martin Zabransky'
;Department of Inorganic Chemistry, Faculty of Science, Charles University, Prague
Czech Republic
;
_audit_update_record             
;
2020-09-14 deposited with the CCDC.	2020-12-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H18 N5 O3, C10 H15 O4 S'
_chemical_formula_sum            'C24 H33 N5 O7 S'
_chemical_formula_weight         535.61

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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   6.7095(4)
_cell_length_b                   11.8584(6)
_cell_length_c                   30.4373(15)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     2421.7(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    961
_cell_measurement_theta_min      3.18
_cell_measurement_theta_max      21.93

_exptl_crystal_description       bar
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.469
_exptl_crystal_F_000             1136
_exptl_transmission_factor_min   0.651
_exptl_transmission_factor_max   0.746
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.02
_exptl_absorpt_coefficient_mu    0.191
_shelx_estimated_absorpt_T_min   0.986
_shelx_estimated_absorpt_T_max   0.996
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.869
_exptl_absorpt_correction_T_max  0.996
_exptl_absorpt_process_details   'SADABS (Bruker,2005)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12850
_diffrn_reflns_av_unetI/netI     0.1341
_diffrn_reflns_av_R_equivalents  0.0905
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_limit_l_max       39
_diffrn_reflns_theta_min         3.109
_diffrn_reflns_theta_max         27.471
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.985
_diffrn_reflns_point_group_measured_fraction_full 0.994
_reflns_number_total             5472
_reflns_number_gt                3484
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.719
_reflns_Friedel_fraction_max     0.967
_reflns_Friedel_fraction_full    0.989

_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-2013/1 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'PLATON (Spek, 2016)'
_computing_publication_material  'PLATON (Spek, 2016)'
_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)+(0.0445P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 991 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.27(13)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         5472
_refine_ls_number_parameters     366
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.1178
_refine_ls_R_factor_gt           0.0607
_refine_ls_wR_factor_ref         0.1310
_refine_ls_wR_factor_gt          0.1155
_refine_ls_goodness_of_fit_ref   0.957
_refine_ls_restrained_S_all      0.957
_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
H1 H 0.180(10) 0.069(5) -0.082(2) 0.05(2) Uiso 1 1 d . . . . .
H2 H 0.141(9) 0.814(4) 0.1230(18) 0.024(16) Uiso 1 1 d . . . . .
H4 H -0.073(9) 0.810(5) 0.1216(18) 0.022(17) Uiso 1 1 d . . . . .
C1 C 0.1953(8) 0.2073(4) -0.03520(16) 0.0150(11) Uani 1 1 d . . . . .
C2 C 0.2091(8) 0.1046(4) -0.01052(15) 0.0148(10) Uani 1 1 d . . . . .
C3 C 0.2285(7) 0.1076(4) 0.03410(15) 0.0153(11) Uani 1 1 d . . . . .
H3 H 0.239632 0.039228 0.048894 0.012(13) Uiso 1 1 calc R . . . .
C4 C 0.2052(8) 0.4975(4) 0.04033(16) 0.0142(11) Uani 1 1 d . . . . .
C5 C 0.2028(8) 0.4180(4) -0.02778(16) 0.0157(11) Uani 1 1 d . . . . .
H5 H 0.202231 0.424327 -0.058234 0.011(13) Uiso 1 1 calc R . . . .
C6 C 0.2030(8) 0.3096(4) -0.00937(16) 0.0128(11) Uani 1 1 d . . . . .
C7 C 0.2157(7) 0.3069(4) 0.03686(15) 0.0117(11) Uani 1 1 d . . . . .
C8 C 0.2047(8) -0.0076(4) -0.03287(17) 0.0174(12) Uani 1 1 d . . . . .
C9 C 0.2540(8) 0.1966(4) 0.10647(15) 0.0171(12) Uani 1 1 d . . . . .
H6 H 0.323631 0.263209 0.116804 0.019(14) Uiso 1 1 calc R . . . .
H7 H 0.333950 0.131272 0.114029 0.035(17) Uiso 1 1 calc R . . . .
C10 C 0.0562(10) 0.1885(6) 0.12924(18) 0.0407(17) Uani 1 1 d . . . . .
H8 H 0.076604 0.184688 0.160425 0.022(14) Uiso 1 1 calc R . . . .
H9 H -0.022485 0.253748 0.122323 0.06(2) Uiso 1 1 calc R . . . .
H10 H -0.012170 0.121870 0.119549 0.07(3) Uiso 1 1 calc R . . . .
C11 C 0.1916(9) 0.7049(4) 0.04443(17) 0.0184(12) Uani 1 1 d . . . . .
H11 H 0.177740 0.698510 0.012806 0.022 Uiso 1 1 calc R U . . .
H12 H 0.316316 0.743103 0.050638 0.022 Uiso 1 1 calc R U . . .
C12 C 0.0200(8) 0.7725(4) 0.06290(15) 0.0162(12) Uani 1 1 d . . . . .
H13 H 0.023971 0.848401 0.051100 0.019 Uiso 1 1 calc R U . . .
H14 H -0.104988 0.738188 0.054015 0.019 Uiso 1 1 calc R U . . .
C13 C 0.2013(8) 0.5929(4) 0.11201(15) 0.0194(12) Uani 1 1 d . . . . .
H16 H 0.326349 0.625653 0.121662 0.023 Uiso 1 1 calc R U . . .
H15 H 0.195049 0.516036 0.122785 0.023 Uiso 1 1 calc R U . . .
C14 C 0.0292(9) 0.6602(4) 0.13070(16) 0.0194(12) Uani 1 1 d . . . . .
H18 H -0.095687 0.623140 0.123650 0.023 Uiso 1 1 calc R U . . .
H17 H 0.040942 0.664077 0.162425 0.023 Uiso 1 1 calc R U . . .
C21 C 0.5733(8) 0.9611(4) 0.20256(15) 0.0155(11) Uani 1 1 d . . . . .
H21A H 0.714359 0.966302 0.209288 0.042(18) Uiso 1 1 calc R . . . .
H21B H 0.527698 1.037450 0.197035 0.001(11) Uiso 1 1 calc R . . . .
C22 C 0.4697(8) 0.9216(4) 0.24448(15) 0.0148(11) Uani 1 1 d . . . . .
C23 C 0.5484(8) 0.9888(4) 0.28368(16) 0.0175(11) Uani 1 1 d . . . . .
C24 C 0.4025(8) 0.9721(5) 0.32091(17) 0.0233(14) Uani 1 1 d . . . . .
H24A H 0.344084 1.043135 0.330111 0.028 Uiso 1 1 calc R U . . .
H24B H 0.465517 0.936270 0.345964 0.028 Uiso 1 1 calc R U . . .
C25 C 0.2466(8) 0.8947(4) 0.29975(16) 0.0199(11) Uani 1 1 d . . . . .
H25 H 0.116965 0.894642 0.314573 0.019(14) Uiso 1 1 calc R . . . .
C26 C 0.3451(9) 0.7779(4) 0.29610(18) 0.0253(14) Uani 1 1 d . . . . .
H26A H 0.249720 0.720960 0.287044 0.07(2) Uiso 1 1 calc R . . . .
H26B H 0.405314 0.755361 0.323706 0.015(14) Uiso 1 1 calc R . . . .
C27 C 0.5066(8) 0.7982(4) 0.25990(17) 0.0204(13) Uani 1 1 d . . . . .
H27B H 0.639650 0.789820 0.271900 0.009(13) Uiso 1 1 calc R . . . .
H27A H 0.490119 0.745744 0.235726 0.009(13) Uiso 1 1 calc R . . . .
C28 C 0.2401(7) 0.9349(4) 0.25143(17) 0.0157(11) Uani 1 1 d . . . . .
C29 C 0.1121(8) 0.8576(5) 0.22297(18) 0.0245(14) Uani 1 1 d . . . . .
H29A H 0.156405 0.781097 0.226336 0.11(3) Uiso 1 1 calc R . . . .
H29B H -0.024640 0.863415 0.231949 0.09(3) Uiso 1 1 calc R . . . .
H29C H 0.124137 0.879623 0.192740 0.035(17) Uiso 1 1 calc R . . . .
C30 C 0.1685(8) 1.0560(4) 0.2458(2) 0.0255(13) Uani 1 1 d . . . . .
H30A H 0.248406 1.105214 0.263637 0.029(16) Uiso 1 1 calc R . . . .
H30B H 0.180409 1.077680 0.215543 0.039(18) Uiso 1 1 calc R . . . .
H30C H 0.031633 1.061471 0.254752 0.040(17) Uiso 1 1 calc R . . . .
N1 N 0.0299(8) 0.7772(4) 0.11181(14) 0.0162(10) Uani 1 1 d . . . . .
N2 N 0.1933(7) 0.5928(3) 0.06419(13) 0.0164(10) Uani 1 1 d . . . . .
N3 N 0.2327(6) 0.2028(3) 0.05810(13) 0.0144(9) Uani 1 1 d . . . . .
N4 N 0.2139(6) 0.3984(3) 0.06198(12) 0.0144(9) Uani 1 1 d . . . . .
N5 N 0.2034(7) 0.5106(3) -0.00450(13) 0.0153(10) Uani 1 1 d . . . . .
O1 O 0.1891(6) -0.0038(3) -0.07616(12) 0.0234(9) Uani 1 1 d . . . . .
O2 O 0.2141(6) -0.0965(3) -0.01325(12) 0.0258(9) Uani 1 1 d . . . . .
O3 O 0.1777(5) 0.2094(3) -0.07637(11) 0.0183(8) Uani 1 1 d . . . . .
O21 O 0.3567(5) 0.9124(3) 0.13341(11) 0.0221(9) Uani 1 1 d . . . . .
O22 O 0.7135(6) 0.9342(3) 0.12508(12) 0.0277(10) Uani 1 1 d . . . . .
O23 O 0.5815(7) 0.7675(3) 0.16005(12) 0.0328(11) Uani 1 1 d . . . . .
O24 O 0.7029(6) 1.0434(3) 0.28469(12) 0.0260(9) Uani 1 1 d . . . . .
S1 S 0.5532(2) 0.88638(11) 0.15154(4) 0.0174(3) 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
C1 O3 1.259(6) . ?
C1 C2 1.435(7) . ?
C1 C6 1.446(7) . ?
C2 C3 1.365(6) . ?
C2 C8 1.494(7) . ?
C3 N3 1.345(6) . ?
C4 N2 1.345(6) . ?
C4 N4 1.349(6) . ?
C4 N5 1.373(6) . ?
C5 N5 1.307(6) . ?
C5 C6 1.402(6) . ?
C6 C7 1.410(7) . ?
C7 N4 1.327(6) . ?
C7 N3 1.399(6) . ?
C8 O2 1.214(6) . ?
C8 O1 1.322(6) . ?
C9 N3 1.481(6) . ?
C9 C10 1.500(8) . ?
C11 N2 1.460(6) . ?
C11 C12 1.511(7) . ?
C12 N1 1.491(6) . ?
C13 N2 1.456(6) . ?
C13 C14 1.515(7) . ?
C14 N1 1.502(6) . ?
C21 C22 1.527(7) . ?
C21 S1 1.793(5) . ?
C22 C23 1.529(7) . ?
C22 C27 1.557(6) . ?
C22 C28 1.563(7) . ?
C23 O24 1.223(6) . ?
C23 C24 1.510(7) . ?
C24 C25 1.533(7) . ?
C25 C26 1.539(7) . ?
C25 C28 1.547(7) . ?
C26 C27 1.564(7) . ?
C28 C30 1.524(7) . ?
C28 C29 1.526(7) . ?
O21 S1 1.462(4) . ?
O22 S1 1.458(4) . ?
O23 S1 1.446(4) . ?

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
O3 C1 C2 123.0(4) . . ?
O3 C1 C6 121.9(5) . . ?
C2 C1 C6 115.2(4) . . ?
C3 C2 C1 120.4(5) . . ?
C3 C2 C8 118.6(5) . . ?
C1 C2 C8 121.1(4) . . ?
N3 C3 C2 124.3(5) . . ?
N2 C4 N4 118.1(4) . . ?
N2 C4 N5 116.2(4) . . ?
N4 C4 N5 125.7(4) . . ?
N5 C5 C6 123.6(4) . . ?
C5 C6 C7 114.8(4) . . ?
C5 C6 C1 123.5(4) . . ?
C7 C6 C1 121.7(5) . . ?
N4 C7 N3 117.1(4) . . ?
N4 C7 C6 123.8(4) . . ?
N3 C7 C6 119.1(4) . . ?
O2 C8 O1 121.6(5) . . ?
O2 C8 C2 123.3(5) . . ?
O1 C8 C2 115.2(4) . . ?
N3 C9 C10 112.1(4) . . ?
N2 C11 C12 109.6(4) . . ?
N1 C12 C11 110.9(4) . . ?
N2 C13 C14 110.4(4) . . ?
N1 C14 C13 109.9(4) . . ?
C22 C21 S1 122.5(3) . . ?
C21 C22 C23 109.6(4) . . ?
C21 C22 C27 117.9(4) . . ?
C23 C22 C27 101.5(4) . . ?
C21 C22 C28 122.1(4) . . ?
C23 C22 C28 100.5(4) . . ?
C27 C22 C28 102.2(4) . . ?
O24 C23 C24 126.9(5) . . ?
O24 C23 C22 126.0(5) . . ?
C24 C23 C22 107.1(4) . . ?
C23 C24 C25 101.8(4) . . ?
C24 C25 C26 106.1(5) . . ?
C24 C25 C28 103.6(4) . . ?
C26 C25 C28 102.8(4) . . ?
C25 C26 C27 102.1(4) . . ?
C22 C27 C26 104.3(4) . . ?
C30 C28 C29 109.0(4) . . ?
C30 C28 C25 113.9(4) . . ?
C29 C28 C25 111.7(4) . . ?
C30 C28 C22 113.0(4) . . ?
C29 C28 C22 114.7(4) . . ?
C25 C28 C22 94.0(4) . . ?
C12 N1 C14 110.3(4) . . ?
C4 N2 C13 122.6(4) . . ?
C4 N2 C11 122.9(4) . . ?
C13 N2 C11 114.2(4) . . ?
C3 N3 C7 119.2(4) . . ?
C3 N3 C9 120.0(4) . . ?
C7 N3 C9 120.7(4) . . ?
C7 N4 C4 115.5(4) . . ?
C5 N5 C4 116.4(4) . . ?
O23 S1 O22 112.4(2) . . ?
O23 S1 O21 113.1(3) . . ?
O22 S1 O21 112.0(2) . . ?
O23 S1 C21 108.5(2) . . ?
O22 S1 C21 103.3(2) . . ?
O21 S1 C21 106.9(2) . . ?

_refine_diff_density_max         0.367
_refine_diff_density_min         -0.353
_refine_diff_density_rms         0.078

####################################################################### 
# 
# 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_CCDC1
_database_code_depnum_ccdc_archive 'CCDC 2031941'
loop_
_audit_author_name
_audit_author_address
'Martin Zabransky'
;Department of Inorganic Chemistry, Faculty of Science, Charles University, Prague
Czech Republic
;
_audit_update_record             
;
2020-09-14 deposited with the CCDC.	2020-12-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H18 N5 O3, C2 H O4'
_chemical_formula_sum            'C16 H19 N5 O7'
_chemical_formula_weight         393.36

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'

_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                   9.8463(8)
_cell_length_b                   9.3601(7)
_cell_length_c                   18.1965(12)
_cell_angle_alpha                90
_cell_angle_beta                 91.888(3)
_cell_angle_gamma                90
_cell_volume                     1676.1(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    2587
_cell_measurement_theta_min      3.00
_cell_measurement_theta_max      27.25

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.559
_exptl_crystal_F_000             824
_exptl_transmission_factor_min   0.705
_exptl_transmission_factor_max   0.746
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.08
_exptl_absorpt_coefficient_mu    0.124
_shelx_estimated_absorpt_T_min   0.974
_shelx_estimated_absorpt_T_max   0.990
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.936
_exptl_absorpt_correction_T_max  0.990
_exptl_absorpt_process_details   'SADABS (Bruker,2005)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            15376
_diffrn_reflns_av_unetI/netI     0.0559
_diffrn_reflns_av_R_equivalents  0.0575
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         3.000
_diffrn_reflns_theta_max         27.772
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             3938
_reflns_number_gt                2813
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-2013/1 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'PLATON (Spek, 2016)'
_computing_publication_material  'PLATON (Spek, 2016)'
_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)+(0.0738P)²+0.0458P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         3938
_refine_ls_number_parameters     269
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0694
_refine_ls_R_factor_gt           0.0430
_refine_ls_wR_factor_ref         0.1223
_refine_ls_wR_factor_gt          0.1100
_refine_ls_goodness_of_fit_ref   0.931
_refine_ls_restrained_S_all      0.931
_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
C1 C 0.50913(17) 0.81558(17) 0.66644(8) 0.0158(3) Uani 1 1 d . . . . .
C2 C 0.62898(17) 0.72796(17) 0.66235(8) 0.0156(3) Uani 1 1 d . . . . .
C3 C 0.67603(17) 0.68856(16) 0.59532(8) 0.0151(3) Uani 1 1 d . . . . .
H3 H 0.754586 0.633483 0.594624 0.018 Uiso 1 1 calc R U . . .
C4 C 0.32372(17) 0.91098(16) 0.46523(8) 0.0136(3) Uani 1 1 d . . . . .
C5 C 0.32726(17) 0.93588(17) 0.58918(9) 0.0160(3) Uani 1 1 d . . . . .
H5 H 0.290551 0.971901 0.631827 0.019 Uiso 1 1 calc R U . . .
C6 C 0.44393(17) 0.84951(16) 0.59658(8) 0.0136(3) Uani 1 1 d . . . . .
C7 C 0.49605(17) 0.80238(15) 0.52977(8) 0.0128(3) Uani 1 1 d . . . . .
C8 C 0.70747(19) 0.68374(17) 0.72949(9) 0.0190(4) Uani 1 1 d . . . . .
C9 C 0.67939(18) 0.68219(17) 0.46091(8) 0.0164(4) Uani 1 1 d . . . . .
H6 H 0.776893 0.674448 0.469391 0.020 Uiso 1 1 calc R U . . .
H7 H 0.662797 0.756446 0.424532 0.020 Uiso 1 1 calc R U . . .
C10 C 0.6257(2) 0.54227(18) 0.43090(10) 0.0275(4) Uani 1 1 d . . . . .
H8 H 0.669817 0.520020 0.386045 0.041 Uiso 1 1 calc R U . . .
H9 H 0.643621 0.467854 0.466210 0.041 Uiso 1 1 calc R U . . .
H10 H 0.529512 0.549861 0.421345 0.041 Uiso 1 1 calc R U . . .
C11 C 0.12698(17) 1.00440(17) 0.39185(9) 0.0169(3) Uani 1 1 d . . . . .
H11 H 0.125207 1.075376 0.352983 0.020 Uiso 1 1 calc R U . . .
H12 H 0.104562 1.051637 0.437319 0.020 Uiso 1 1 calc R U . . .
C12 C 0.02269(17) 0.88947(17) 0.37403(8) 0.0160(3) Uani 1 1 d . . . . .
H13 H 0.013508 0.827767 0.416406 0.019 Uiso 1 1 calc R U . . .
H14 H -0.064838 0.933547 0.363168 0.019 Uiso 1 1 calc R U . . .
C13 C 0.30207(17) 0.86810(18) 0.33271(8) 0.0175(4) Uani 1 1 d . . . . .
H15 H 0.394198 0.832285 0.338779 0.021 Uiso 1 1 calc R U . . .
H16 H 0.298811 0.933667 0.291412 0.021 Uiso 1 1 calc R U . . .
C14 C 0.20528(18) 0.74544(17) 0.31807(9) 0.0170(4) Uani 1 1 d . . . . .
H17 H 0.229527 0.695890 0.273553 0.020 Uiso 1 1 calc R U . . .
H18 H 0.211014 0.678069 0.358554 0.020 Uiso 1 1 calc R U . . .
N1 N 0.06353(15) 0.80238(16) 0.30969(8) 0.0157(3) Uani 1 1 d . . . . .
N2 N 0.26318(14) 0.94233(14) 0.39938(7) 0.0160(3) Uani 1 1 d . . . . .
N3 N 0.61609(14) 0.72428(14) 0.53044(7) 0.0135(3) Uani 1 1 d . . . . .
N4 N 0.43650(14) 0.83003(14) 0.46459(7) 0.0144(3) Uani 1 1 d . . . . .
N5 N 0.26695(14) 0.96889(14) 0.52622(7) 0.0161(3) Uani 1 1 d . . . . .
O1 O 0.65731(14) 0.72882(14) 0.79225(6) 0.0253(3) Uani 1 1 d . . . . .
O2 O 0.81070(13) 0.61296(14) 0.72836(6) 0.0276(3) Uani 1 1 d . . . . .
O3 O 0.46531(13) 0.86010(13) 0.72643(6) 0.0224(3) Uani 1 1 d . . . . .
C21 C 0.07171(19) 0.67296(17) 0.61210(9) 0.0187(4) Uani 1 1 d . . . . .
C22 C 0.04419(18) 0.51394(17) 0.63045(8) 0.0166(4) Uani 1 1 d . . . . .
O21 O 0.05753(16) 0.70684(13) 0.54149(6) 0.0297(3) Uani 1 1 d . . . . .
O22 O 0.10147(15) 0.76079(13) 0.65794(6) 0.0271(3) Uani 1 1 d . . . . .
O23 O 0.07638(13) 0.47305(12) 0.69355(6) 0.0195(3) Uani 1 1 d . . . . .
O24 O -0.00890(15) 0.44350(13) 0.57887(6) 0.0300(3) Uani 1 1 d . . . . .
H1 H 0.578(3) 0.789(3) 0.7765(13) 0.057(8) Uiso 1 1 d . . . . .
H2 H 0.007(2) 0.727(2) 0.3039(10) 0.025(5) Uiso 1 1 d . . . . .
H4 H 0.059(2) 0.853(2) 0.2706(12) 0.036(6) Uiso 1 1 d . . . . .
H21 H 0.033(3) 0.629(3) 0.5148(13) 0.053(7) 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
C1 O3 1.2580(19) . ?
C1 C6 1.441(2) . ?
C1 C2 1.441(2) . ?
C2 C3 1.370(2) . ?
C2 C8 1.483(2) . ?
C3 N3 1.345(2) . ?
C4 N4 1.345(2) . ?
C4 N2 1.353(2) . ?
C4 N5 1.3707(19) . ?
C5 N5 1.310(2) . ?
C5 C6 1.408(2) . ?
C6 C7 1.406(2) . ?
C7 N4 1.331(2) . ?
C7 N3 1.389(2) . ?
C8 O2 1.214(2) . ?
C8 O1 1.328(2) . ?
C9 N3 1.4820(19) . ?
C9 C10 1.508(2) . ?
C11 N2 1.464(2) . ?
C11 C12 1.515(2) . ?
C12 N1 1.493(2) . ?
C13 N2 1.4600(19) . ?
C13 C14 1.510(2) . ?
C14 N1 1.497(2) . ?
C21 O22 1.201(2) . ?
C21 O21 1.326(2) . ?
C21 C22 1.551(2) . ?
C22 O23 1.2414(19) . ?
C22 O24 1.248(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
O3 C1 C6 122.49(15) . . ?
O3 C1 C2 122.57(15) . . ?
C6 C1 C2 114.94(13) . . ?
C3 C2 C1 120.06(15) . . ?
C3 C2 C8 118.44(15) . . ?
C1 C2 C8 121.45(14) . . ?
N3 C3 C2 124.30(16) . . ?
N4 C4 N2 117.03(13) . . ?
N4 C4 N5 126.07(14) . . ?
N2 C4 N5 116.86(14) . . ?
N5 C5 C6 124.34(14) . . ?
C7 C6 C5 114.68(14) . . ?
C7 C6 C1 121.94(15) . . ?
C5 C6 C1 123.34(14) . . ?
N4 C7 N3 117.37(13) . . ?
N4 C7 C6 123.15(15) . . ?
N3 C7 C6 119.48(14) . . ?
O2 C8 O1 121.56(16) . . ?
O2 C8 C2 123.52(15) . . ?
O1 C8 C2 114.92(15) . . ?
N3 C9 C10 112.82(13) . . ?
N2 C11 C12 110.52(13) . . ?
N1 C12 C11 110.94(13) . . ?
N2 C13 C14 109.10(13) . . ?
N1 C14 C13 109.15(13) . . ?
C12 N1 C14 112.89(13) . . ?
C4 N2 C13 120.85(14) . . ?
C4 N2 C11 123.00(13) . . ?
C13 N2 C11 112.06(13) . . ?
C3 N3 C7 119.15(13) . . ?
C3 N3 C9 119.91(14) . . ?
C7 N3 C9 120.93(13) . . ?
C7 N4 C4 116.20(13) . . ?
C5 N5 C4 115.45(14) . . ?
O22 C21 O21 121.66(15) . . ?
O22 C21 C22 123.22(15) . . ?
O21 C21 C22 115.12(14) . . ?
O23 C22 O24 128.37(15) . . ?
O23 C22 C21 116.99(14) . . ?
O24 C22 C21 114.64(14) . . ?

_refine_diff_density_max         0.290
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.059

####################################################################### 
# 
# 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_PACu
_database_code_depnum_ccdc_archive 'CCDC 2031943'
loop_
_audit_author_name
_audit_author_address
'Vania Andre'
;CQE, Instituto Superior Tecnico
Portugal
;
_audit_update_record             
;
2020-09-14 deposited with the CCDC.	2020-12-18 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         ?
_chemical_formula_sum            'C28 H34 Cu1 N12 O12'
_chemical_formula_weight         794.22

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'
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           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                   12.1073(9)
_cell_length_b                   6.2472(5)
_cell_length_c                   21.3210(15)
_cell_angle_alpha                90
_cell_angle_beta                 94.374(4)
_cell_angle_gamma                90
_cell_volume                     1608.0(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    296(2)
_cell_measurement_reflns_used    3272
_cell_measurement_theta_min      2.455
_cell_measurement_theta_max      26.445

_exptl_crystal_description       cube
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.640
_exptl_crystal_F_000             822
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.120
_exptl_crystal_size_mid          0.040
_exptl_crystal_size_min          0.040
_exptl_absorpt_coefficient_mu    0.765
_shelx_estimated_absorpt_T_min   0.914
_shelx_estimated_absorpt_T_max   0.970
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6790
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_process_details   'SADABS (Bruker,2014)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      296(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            27329
_diffrn_reflns_av_unetI/netI     0.1159
_diffrn_reflns_av_R_equivalents  0.1479
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.455
_diffrn_reflns_theta_max         26.445
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.988
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.988
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.988
_reflns_number_total             3272
_reflns_number_gt                1782
_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 SMART (Bruker, 2014)'
_computing_cell_refinement       'BRUKER SMART (Bruker, 2014)'
_computing_data_reduction        'BRUKER SAINT (Bruker, 2014)'
_computing_structure_solution    'SHELXT 2014/4 (Sheldrick, 2015)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_molecular_graphics    'Mercury 2020.1'
_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)+(0.0618P)²] 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         3272
_refine_ls_number_parameters     247
_refine_ls_number_restraints     2
_refine_ls_R_factor_all          0.1353
_refine_ls_R_factor_gt           0.0571
_refine_ls_wR_factor_ref         0.1469
_refine_ls_wR_factor_gt          0.1171
_refine_ls_goodness_of_fit_ref   1.003
_refine_ls_restrained_S_all      1.003
_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
C1 C 0.0896(3) 0.6289(7) 0.44467(18) 0.0272(10) Uani 1 1 d . . . . .
C2 C -0.0138(3) 0.5553(6) 0.41877(18) 0.0270(10) Uani 1 1 d . . . . .
C3 C -0.0180(3) 0.3674(6) 0.38422(19) 0.0303(10) Uani 1 1 d . . . . .
H3 H -0.0869 0.3213 0.3672 0.036 Uiso 1 1 calc R U . . .
C4 C 0.3579(3) 0.2594(7) 0.4077(2) 0.0334(11) Uani 1 1 d . . . . .
C5 C 0.2909(3) 0.5483(7) 0.4554(2) 0.0382(12) Uani 1 1 d . . . . .
H5 H 0.3015 0.6714 0.4796 0.046 Uiso 1 1 calc R U . . .
C6 C 0.1838(3) 0.4974(7) 0.43369(17) 0.0284(9) Uani 1 1 d . . . . .
C7 C 0.1732(3) 0.3107(6) 0.39790(17) 0.0248(9) Uani 1 1 d . . . . .
C8 C -0.1201(3) 0.6697(7) 0.42536(19) 0.0302(10) Uani 1 1 d . . . . .
C9 C 0.0599(3) 0.0604(6) 0.33065(19) 0.0328(11) Uani 1 1 d . . . . .
H9A H -0.0159 0.0089 0.3283 0.039 Uiso 1 1 calc R U . . .
H9B H 0.1073 -0.0539 0.3478 0.039 Uiso 1 1 calc R U . . .
C10 C 0.0908(4) 0.1133(8) 0.2659(2) 0.0512(14) Uani 1 1 d . . . . .
H10A H 0.0830 -0.0120 0.2399 0.077 Uiso 1 1 calc R U . . .
H10B H 0.0430 0.2243 0.2484 0.077 Uiso 1 1 calc R U . . .
H10C H 0.1663 0.1615 0.2679 0.077 Uiso 1 1 calc R U . . .
C11 C 0.4392(4) -0.0212(8) 0.3461(2) 0.0506(13) Uani 1 1 d . . . . .
H11A H 0.4541 0.0393 0.3058 0.061 Uiso 1 1 calc R U . . .
H11B H 0.3645 -0.0786 0.3427 0.061 Uiso 1 1 calc R U . . .
C12 C 0.5208(4) -0.1985(8) 0.3632(3) 0.0490(13) Uani 1 1 d . . . . .
H12A H 0.5003 -0.2701 0.4009 0.059 Uiso 1 1 calc R U . . .
H12B H 0.5184 -0.3030 0.3294 0.059 Uiso 1 1 calc R U . . .
C13 C 0.5598(4) 0.2326(8) 0.4044(3) 0.0512(14) Uani 1 1 d . . . . .
H13A H 0.5615 0.3399 0.4374 0.061 Uiso 1 1 calc R U . . .
H13B H 0.5809 0.3008 0.3662 0.061 Uiso 1 1 calc R U . . .
C14 C 0.6406(4) 0.0559(8) 0.4232(2) 0.0528(14) Uani 1 1 d . . . . .
H14A H 0.7152 0.1134 0.4283 0.063 Uiso 1 1 calc R U . . .
H14B H 0.6229 -0.0052 0.4630 0.063 Uiso 1 1 calc R U . . .
N1 N 0.6344(3) -0.1128(6) 0.37384(18) 0.0379(10) Uani 1 1 d D . . . .
N2 N 0.4480(3) 0.1449(6) 0.39400(18) 0.0416(10) Uani 1 1 d . . . . .
N3 N 0.0701(3) 0.2478(5) 0.37371(15) 0.0261(8) Uani 1 1 d . . . . .
N4 N 0.2589(3) 0.1877(5) 0.38554(15) 0.0293(8) Uani 1 1 d . . . . .
N5 N 0.3786(3) 0.4359(6) 0.44434(18) 0.0458(11) Uani 1 1 d . . . . .
N6 N 0.7340(4) 0.0845(7) 0.2437(2) 0.0550(12) Uani 1 1 d . . . . .
O1 O -0.1181(2) 0.8500(5) 0.45382(13) 0.0374(8) Uani 1 1 d . . . . .
O2 O -0.2071(2) 0.5872(5) 0.40295(15) 0.0429(8) Uani 1 1 d . . . . .
O3 O 0.1073(2) 0.8009(4) 0.47683(13) 0.0342(7) Uani 1 1 d . . . . .
O4 O 0.7804(4) 0.1414(6) 0.1978(2) 0.0825(14) Uani 1 1 d . . . . .
O5 O 0.6417(4) 0.0028(8) 0.23854(19) 0.0874(13) Uani 1 1 d . . . . .
O6 O 0.7795(4) 0.1067(7) 0.2972(2) 0.0820(13) Uani 1 1 d . . . . .
Cu1 Cu 0.0000 1.0000 0.5000 0.0333(3) Uani 1 2 d S . P . .
H2 H 0.678(3) -0.226(5) 0.3816(18) 0.040 Uiso 1 1 d D U . . .
H4 H 0.657(3) -0.060(6) 0.3378(13) 0.040 Uiso 1 1 d D 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
C1 O3 1.284(5) . ?
C1 C2 1.407(6) . ?
C1 C6 1.439(5) . ?
C2 C3 1.385(5) . ?
C2 C8 1.489(5) . ?
C3 N3 1.335(5) . ?
C3 H3 0.9300 . ?
C4 N4 1.331(5) . ?
C4 N2 1.355(5) . ?
C4 N5 1.364(5) . ?
C5 N5 1.309(5) . ?
C5 C6 1.380(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.394(5) . ?
C7 N4 1.334(5) . ?
C7 N3 1.371(5) . ?
C8 O2 1.235(5) . ?
C8 O1 1.279(5) . ?
C9 N3 1.487(5) . ?
C9 C10 1.495(6) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
C11 N2 1.454(5) . ?
C11 C12 1.510(6) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 N1 1.477(6) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 N2 1.461(6) . ?
C13 C14 1.508(6) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 N1 1.487(6) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
N1 H2 0.890(19) . ?
N1 H4 0.897(19) . ?
N6 O4 1.219(5) . ?
N6 O5 1.225(5) . ?
N6 O6 1.235(5) . ?
O1 Cu1 1.918(3) . ?
O3 Cu1 1.891(3) . ?
Cu1 O3 1.891(3) 3_576 ?
Cu1 O1 1.918(3) 3_576 ?

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
O3 C1 C2 126.2(4) . . ?
O3 C1 C6 117.6(4) . . ?
C2 C1 C6 116.2(4) . . ?
C3 C2 C1 118.8(4) . . ?
C3 C2 C8 117.4(4) . . ?
C1 C2 C8 123.8(4) . . ?
N3 C3 C2 124.5(4) . . ?
N3 C3 H3 117.8 . . ?
C2 C3 H3 117.8 . . ?
N4 C4 N2 117.6(4) . . ?
N4 C4 N5 126.6(4) . . ?
N2 C4 N5 115.8(4) . . ?
N5 C5 C6 124.8(4) . . ?
N5 C5 H5 117.6 . . ?
C6 C5 H5 117.6 . . ?
C5 C6 C7 114.9(4) . . ?
C5 C6 C1 123.3(4) . . ?
C7 C6 C1 121.7(4) . . ?
N4 C7 N3 117.4(3) . . ?
N4 C7 C6 123.3(4) . . ?
N3 C7 C6 119.3(3) . . ?
O2 C8 O1 122.4(4) . . ?
O2 C8 C2 118.8(4) . . ?
O1 C8 C2 118.8(4) . . ?
N3 C9 C10 112.4(3) . . ?
N3 C9 H9A 109.1 . . ?
C10 C9 H9A 109.1 . . ?
N3 C9 H9B 109.1 . . ?
C10 C9 H9B 109.1 . . ?
H9A C9 H9B 107.9 . . ?
C9 C10 H10A 109.5 . . ?
C9 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
C9 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
N2 C11 C12 110.1(4) . . ?
N2 C11 H11A 109.6 . . ?
C12 C11 H11A 109.6 . . ?
N2 C11 H11B 109.6 . . ?
C12 C11 H11B 109.6 . . ?
H11A C11 H11B 108.2 . . ?
N1 C12 C11 110.8(4) . . ?
N1 C12 H12A 109.5 . . ?
C11 C12 H12A 109.5 . . ?
N1 C12 H12B 109.5 . . ?
C11 C12 H12B 109.5 . . ?
H12A C12 H12B 108.1 . . ?
N2 C13 C14 109.9(4) . . ?
N2 C13 H13A 109.7 . . ?
C14 C13 H13A 109.7 . . ?
N2 C13 H13B 109.7 . . ?
C14 C13 H13B 109.7 . . ?
H13A C13 H13B 108.2 . . ?
N1 C14 C13 109.5(4) . . ?
N1 C14 H14A 109.8 . . ?
C13 C14 H14A 109.8 . . ?
N1 C14 H14B 109.8 . . ?
C13 C14 H14B 109.8 . . ?
H14A C14 H14B 108.2 . . ?
C12 N1 C14 111.3(4) . . ?
C12 N1 H2 106(3) . . ?
C14 N1 H2 116(3) . . ?
C12 N1 H4 110(3) . . ?
C14 N1 H4 110(3) . . ?
H2 N1 H4 104(4) . . ?
C4 N2 C11 120.7(4) . . ?
C4 N2 C13 121.4(4) . . ?
C11 N2 C13 113.1(4) . . ?
C3 N3 C7 119.5(3) . . ?
C3 N3 C9 120.9(3) . . ?
C7 N3 C9 119.2(3) . . ?
C4 N4 C7 115.4(3) . . ?
C5 N5 C4 114.9(4) . . ?
O4 N6 O5 121.4(5) . . ?
O4 N6 O6 120.5(5) . . ?
O5 N6 O6 118.0(5) . . ?
C8 O1 Cu1 131.3(3) . . ?
C1 O3 Cu1 126.9(3) . . ?
O3 Cu1 O3 180.0 3_576 . ?
O3 Cu1 O1 87.45(12) 3_576 . ?
O3 Cu1 O1 92.55(12) . . ?
O3 Cu1 O1 92.55(12) 3_576 3_576 ?
O3 Cu1 O1 87.45(12) . 3_576 ?
O1 Cu1 O1 180.0 . 3_576 ?

_refine_diff_density_max         0.340
_refine_diff_density_min         -0.465
_refine_diff_density_rms         0.085

####################################################################### 
# 
# 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_CCDC2
_database_code_depnum_ccdc_archive 'CCDC 2031942'
loop_
_audit_author_name
_audit_author_address
'Martin Zabransky'
;Department of Inorganic Chemistry, Faculty of Science, Charles University, Prague
Czech Republic
;
_audit_update_record             
;
2020-09-14 deposited with the CCDC.	2020-12-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H18 N5 O3, C2 H3 O3, 2(H2 O)'
_chemical_formula_sum            'C16 H25 N5 O8'
_chemical_formula_weight         415.41

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'

_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                   7.2922(3)
_cell_length_b                   7.8666(3)
_cell_length_c                   17.1901(6)
_cell_angle_alpha                81.064(2)
_cell_angle_beta                 79.634(2)
_cell_angle_gamma                80.387(2)
_cell_volume                     948.38(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    4802
_cell_measurement_theta_min      2.77
_cell_measurement_theta_max      32.93

_exptl_crystal_description       bar
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.455
_exptl_crystal_F_000             440
_exptl_transmission_factor_min   0.685
_exptl_transmission_factor_max   0.747
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.08
_exptl_absorpt_coefficient_mu    0.118
_shelx_estimated_absorpt_T_min   0.975
_shelx_estimated_absorpt_T_max   0.991
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.909
_exptl_absorpt_correction_T_max  0.991
_exptl_absorpt_process_details   'SADABS (Bruker,2005)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            27174
_diffrn_reflns_av_unetI/netI     0.0699
_diffrn_reflns_av_R_equivalents  0.0680
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_l_min       -26
_diffrn_reflns_limit_l_max       26
_diffrn_reflns_theta_min         2.869
_diffrn_reflns_theta_max         33.813
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measured_fraction_theta_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_point_group_measured_fraction_full 0.998
_reflns_number_total             7545
_reflns_number_gt                4749
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-2013/1 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'PLATON (Spek, 2016)'
_computing_publication_material  'PLATON (Spek, 2016)'
_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)+(0.0736P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         7545
_refine_ls_number_parameters     294
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0937
_refine_ls_R_factor_gt           0.0509
_refine_ls_wR_factor_ref         0.1389
_refine_ls_wR_factor_gt          0.1234
_refine_ls_goodness_of_fit_ref   0.945
_refine_ls_restrained_S_all      0.945
_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
C1 C 0.78776(15) 0.05364(14) -0.04333(6) 0.0133(2) Uani 1 1 d . . . . .
C2 C 0.85484(15) -0.13004(14) -0.03589(7) 0.0130(2) Uani 1 1 d . . . . .
C3 C 0.80178(16) -0.23509(14) 0.03342(7) 0.0140(2) Uani 1 1 d . . . . .
H3 H 0.848724 -0.352964 0.036753 0.017 Uiso 1 1 calc R U . . .
C4 C 0.44010(15) 0.22031(14) 0.15598(6) 0.0125(2) Uani 1 1 d . . . . .
C5 C 0.59261(16) 0.28835(14) 0.02998(7) 0.0144(2) Uani 1 1 d . . . . .
H5 H 0.623430 0.369249 -0.014033 0.017 Uiso 1 1 calc R U . . .
C6 C 0.66811(15) 0.11318(13) 0.02578(6) 0.0121(2) Uani 1 1 d . . . . .
C7 C 0.61749(15) -0.00090(13) 0.09487(6) 0.01116(19) Uani 1 1 d . . . . .
C8 C 0.98400(16) -0.20960(15) -0.10161(7) 0.0159(2) Uani 1 1 d . . . . .
C9 C 0.63230(17) -0.29817(14) 0.16929(7) 0.0170(2) Uani 1 1 d . . . . .
H6 H 0.657323 -0.416008 0.155848 0.020 Uiso 1 1 calc R U . . .
H7 H 0.498293 -0.271881 0.187962 0.020 Uiso 1 1 calc R U . . .
C10 C 0.73921(19) -0.28701(17) 0.23526(8) 0.0240(3) Uani 1 1 d . . . . .
H8 H 0.700975 -0.367630 0.280913 0.036 Uiso 1 1 calc R U . . .
H9 H 0.871844 -0.315182 0.217378 0.036 Uiso 1 1 calc R U . . .
H10 H 0.712892 -0.171126 0.249476 0.036 Uiso 1 1 calc R U . . .
C11 C 0.21844(17) 0.45088(14) 0.21842(7) 0.0167(2) Uani 1 1 d . . . . .
H11 H 0.086923 0.444031 0.218277 0.020 Uiso 1 1 calc R U . . .
H12 H 0.264450 0.522533 0.169962 0.020 Uiso 1 1 calc R U . . .
C12 C 0.23662(18) 0.53266(15) 0.29017(7) 0.0179(2) Uani 1 1 d . . . . .
H13 H 0.366843 0.547341 0.288349 0.022 Uiso 1 1 calc R U . . .
H14 H 0.160744 0.646427 0.289471 0.022 Uiso 1 1 calc R U . . .
C13 C 0.27096(18) 0.15976(15) 0.29276(7) 0.0185(2) Uani 1 1 d . . . . .
H15 H 0.354340 0.049949 0.292323 0.022 Uiso 1 1 calc R U . . .
H16 H 0.143648 0.136957 0.294149 0.022 Uiso 1 1 calc R U . . .
C14 C 0.28070(18) 0.24070(16) 0.36609(7) 0.0200(2) Uani 1 1 d . . . . .
H17 H 0.230157 0.168204 0.413405 0.024 Uiso 1 1 calc R U . . .
H18 H 0.411306 0.245705 0.368942 0.024 Uiso 1 1 calc R U . . .
C21 C 0.75386(16) 0.38462(15) 0.46253(7) 0.0164(2) Uani 1 1 d . . . . .
C22 C 0.66980(19) 0.23609(17) 0.51739(7) 0.0227(3) Uani 1 1 d . . . . .
H22A H 0.536318 0.249222 0.514774 0.027 Uiso 1 1 calc R U . . .
H22B H 0.728124 0.127163 0.498101 0.027 Uiso 1 1 calc R U . . .
N1 N 0.17264(15) 0.41967(13) 0.36460(6) 0.0169(2) Uani 1 1 d . . . . .
N2 N 0.32629(14) 0.27703(12) 0.22050(6) 0.0161(2) Uani 1 1 d . . . . .
N3 N 0.68527(13) -0.17629(11) 0.09682(6) 0.01311(18) Uani 1 1 d . . . . .
N4 N 0.50443(13) 0.04969(12) 0.15937(5) 0.01300(18) Uani 1 1 d . . . . .
N5 N 0.48078(14) 0.34475(12) 0.09255(6) 0.01506(19) Uani 1 1 d . . . . .
O1 O 1.02731(13) -0.09766(12) -0.16665(5) 0.0220(2) Uani 1 1 d . . . . .
O2 O 1.04811(13) -0.36211(11) -0.09841(5) 0.0231(2) Uani 1 1 d . . . . .
O1W O 0.74076(14) 0.09279(13) 0.32420(6) 0.0259(2) Uani 1 1 d . . . . .
O3 O 0.83132(12) 0.15562(10) -0.10638(5) 0.01884(19) Uani 1 1 d . . . . .
O2W O 0.92624(17) 0.80830(16) 0.41180(8) 0.0401(3) Uani 1 1 d . . . . .
O21 O 0.77955(13) 0.51357(11) 0.49157(5) 0.0224(2) Uani 1 1 d . . . . .
O22 O 0.79615(13) 0.36828(12) 0.38926(5) 0.0228(2) Uani 1 1 d . . . . .
O23 O 0.69312(16) 0.22744(13) 0.59774(6) 0.0279(2) Uani 1 1 d . . . . .
H1 H 0.963(3) 0.010(3) -0.1546(12) 0.059(6) Uiso 1 1 d . . . . .
H1A H 0.763(3) 0.189(3) 0.3462(12) 0.059(6) Uiso 1 1 d . . . . .
H1B H 0.794(3) 0.102(3) 0.2774(14) 0.065(7) Uiso 1 1 d . . . . .
H2 H 0.039(2) 0.416(2) 0.3672(9) 0.025(4) Uiso 1 1 d . . . . .
H2A H 0.872(3) 0.726(3) 0.4240(12) 0.050(6) Uiso 1 1 d . . . . .
H2B H 0.854(3) 0.892(3) 0.3833(13) 0.061(6) Uiso 1 1 d . . . . .
H4 H 0.189(2) 0.472(2) 0.4097(11) 0.037(5) Uiso 1 1 d . . . . .
H23 H 0.810(3) 0.206(2) 0.5969(10) 0.031(5) 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
C1 O3 1.2689(13) . ?
C1 C6 1.4336(15) . ?
C1 C2 1.4396(15) . ?
C2 C3 1.3737(15) . ?
C2 C8 1.4816(16) . ?
C3 N3 1.3475(14) . ?
C4 N4 1.3417(14) . ?
C4 N2 1.3478(14) . ?
C4 N5 1.3727(13) . ?
C5 N5 1.3155(14) . ?
C5 C6 1.4037(15) . ?
C6 C7 1.4051(14) . ?
C7 N4 1.3289(14) . ?
C7 N3 1.3830(13) . ?
C8 O2 1.2093(14) . ?
C8 O1 1.3361(14) . ?
C9 N3 1.4833(13) . ?
C9 C10 1.5077(18) . ?
C11 N2 1.4581(14) . ?
C11 C12 1.5121(17) . ?
C12 N1 1.4883(14) . ?
C13 N2 1.4646(14) . ?
C13 C14 1.5152(17) . ?
C14 N1 1.4931(16) . ?
C21 O21 1.2520(14) . ?
C21 O22 1.2631(14) . ?
C21 C22 1.5229(16) . ?
C22 O23 1.4117(16) . ?

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
O3 C1 C6 122.36(10) . . ?
O3 C1 C2 122.53(10) . . ?
C6 C1 C2 115.11(9) . . ?
C3 C2 C1 120.21(10) . . ?
C3 C2 C8 118.56(10) . . ?
C1 C2 C8 121.22(10) . . ?
N3 C3 C2 123.44(10) . . ?
N4 C4 N2 117.86(9) . . ?
N4 C4 N5 125.93(10) . . ?
N2 C4 N5 116.21(10) . . ?
N5 C5 C6 123.81(10) . . ?
C5 C6 C7 114.83(10) . . ?
C5 C6 C1 123.08(9) . . ?
C7 C6 C1 122.09(10) . . ?
N4 C7 N3 117.15(9) . . ?
N4 C7 C6 123.56(10) . . ?
N3 C7 C6 119.29(10) . . ?
O2 C8 O1 121.33(11) . . ?
O2 C8 C2 124.35(11) . . ?
O1 C8 C2 114.33(10) . . ?
N3 C9 C10 112.09(9) . . ?
N2 C11 C12 110.17(10) . . ?
N1 C12 C11 109.71(9) . . ?
N2 C13 C14 110.09(9) . . ?
N1 C14 C13 111.66(10) . . ?
O21 C21 O22 123.65(11) . . ?
O21 C21 C22 119.37(11) . . ?
O22 C21 C22 116.98(11) . . ?
O23 C22 C21 113.80(10) . . ?
C12 N1 C14 111.25(9) . . ?
C4 N2 C11 122.53(9) . . ?
C4 N2 C13 122.47(9) . . ?
C11 N2 C13 113.86(9) . . ?
C3 N3 C7 119.83(9) . . ?
C3 N3 C9 120.34(9) . . ?
C7 N3 C9 119.82(9) . . ?
C7 N4 C4 116.05(9) . . ?
C5 N5 C4 115.80(9) . . ?

_refine_diff_density_max         0.435
_refine_diff_density_min         -0.377
_refine_diff_density_rms         0.089

####################################################################### 
# 
# 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_CCDC3
_database_code_depnum_ccdc_archive 'CCDC 2031939'
loop_
_audit_author_name
_audit_author_address
'Martin Zabransky'
;Department of Inorganic Chemistry, Faculty of Science, Charles University, Prague
Czech Republic
;
_audit_update_record             
;
2020-09-14 deposited with the CCDC.	2020-12-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         '2(C14 H18 N5 O3), C2 O4, 5(H2 O)'
_chemical_formula_sum            'C30 H46 N10 O15'
_chemical_formula_weight         786.77

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'

_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                   7.5920(3)
_cell_length_b                   15.4924(7)
_cell_length_c                   16.2129(8)
_cell_angle_alpha                72.946(3)
_cell_angle_beta                 83.283(2)
_cell_angle_gamma                81.684(2)
_cell_volume                     1798.30(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    5537
_cell_measurement_theta_min      2.71
_cell_measurement_theta_max      27.33

_exptl_crystal_description       plate
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      'not measured'
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.453
_exptl_crystal_F_000             832
_exptl_transmission_factor_min   0.690
_exptl_transmission_factor_max   0.746
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.20
_exptl_absorpt_coefficient_mu    0.118
_shelx_estimated_absorpt_T_min   0.967
_shelx_estimated_absorpt_T_max   0.977
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.904
_exptl_absorpt_correction_T_max  0.977
_exptl_absorpt_process_details   'SADABS (Bruker,2005)'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus sealed tube'
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            31823
_diffrn_reflns_av_unetI/netI     0.0680
_diffrn_reflns_av_R_equivalents  0.0612
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         1.621
_diffrn_reflns_theta_max         27.595
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             8306
_reflns_number_gt                5306
_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 APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-2013/1 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'PLATON (Spek, 2016)'
_computing_publication_material  'PLATON (Spek, 2016)'
_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)+(0.0597P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         8306
_refine_ls_number_parameters     560
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0896
_refine_ls_R_factor_gt           0.0472
_refine_ls_wR_factor_ref         0.1195
_refine_ls_wR_factor_gt          0.1066
_refine_ls_goodness_of_fit_ref   0.960
_refine_ls_restrained_S_all      0.960
_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
C1 C 0.41712(18) 0.25834(12) 1.00551(11) 0.0194(4) Uani 1 1 d . . . . .
C2 C 0.59967(18) 0.20529(11) 0.98663(11) 0.0182(4) Uani 1 1 d . . . . .
C101 C 0.20033(17) -0.02798(11) 0.55575(11) 0.0156(4) Uani 1 1 d . . . . .
C102 C 0.11998(17) 0.06487(11) 0.54414(11) 0.0157(4) Uani 1 1 d . . . . .
C103 C 0.15700(17) 0.13012(11) 0.46958(11) 0.0170(4) Uani 1 1 d . . . . .
H103 H 0.102184 0.188984 0.464310 0.020 Uiso 1 1 calc R U . . .
C104 C 0.53275(17) -0.06824(11) 0.34612(10) 0.0151(4) Uani 1 1 d . . . . .
C105 C 0.40324(18) -0.12855(11) 0.48032(11) 0.0178(4) Uani 1 1 d . . . . .
H105 H 0.384580 -0.177992 0.528111 0.021 Uiso 1 1 calc R U . . .
C106 C 0.31563(17) -0.04307(11) 0.48275(10) 0.0143(3) Uani 1 1 d . . . . .
C107 C 0.34811(17) 0.02734(10) 0.40802(10) 0.0139(3) Uani 1 1 d . . . . .
C108 C -0.00508(18) 0.09173(12) 0.61171(11) 0.0184(4) Uani 1 1 d . . . . .
C109 C 0.3026(2) 0.18959(11) 0.32390(11) 0.0211(4) Uani 1 1 d . . . . .
H106 H 0.429463 0.185142 0.306399 0.025 Uiso 1 1 calc R U . . .
H107 H 0.268663 0.247325 0.336828 0.025 Uiso 1 1 calc R U . . .
C110 C 0.2010(2) 0.18732(12) 0.25014(12) 0.0289(4) Uani 1 1 d . . . . .
H108 H 0.227136 0.236796 0.200376 0.043 Uiso 1 1 calc R U . . .
H109 H 0.235946 0.130782 0.236334 0.043 Uiso 1 1 calc R U . . .
H110 H 0.075207 0.192941 0.266752 0.043 Uiso 1 1 calc R U . . .
C111 C 0.74524(19) -0.16730(11) 0.27565(11) 0.0197(4) Uani 1 1 d . . . . .
H111 H 0.717787 -0.213634 0.328854 0.024 Uiso 1 1 calc R U . . .
H112 H 0.871997 -0.161944 0.270882 0.024 Uiso 1 1 calc R U . . .
C112 C 0.69988(19) -0.19481(11) 0.19952(11) 0.0206(4) Uani 1 1 d . . . . .
H113 H 0.774394 -0.250181 0.195890 0.025 Uiso 1 1 calc R U . . .
H114 H 0.576206 -0.206824 0.207582 0.025 Uiso 1 1 calc R U . . .
C113 C 0.6717(2) -0.00728(11) 0.19919(11) 0.0208(4) Uani 1 1 d . . . . .
H115 H 0.795543 0.004397 0.191163 0.025 Uiso 1 1 calc R U . . .
H116 H 0.597650 0.047878 0.203854 0.025 Uiso 1 1 calc R U . . .
C114 C 0.6246(2) -0.03359(12) 0.12242(11) 0.0223(4) Uani 1 1 d . . . . .
H117 H 0.497836 -0.039163 0.127709 0.027 Uiso 1 1 calc R U . . .
H118 H 0.650626 0.013525 0.069589 0.027 Uiso 1 1 calc R U . . .
C201 C 0.77282(18) 0.54465(11) 0.45427(11) 0.0167(4) Uani 1 1 d . . . . .
C202 C 0.84129(17) 0.45191(11) 0.45953(11) 0.0160(4) Uani 1 1 d . . . . .
C203 C 0.79865(17) 0.38369(11) 0.53129(10) 0.0160(4) Uani 1 1 d . . . . .
H203 H 0.845180 0.324412 0.532636 0.019 Uiso 1 1 calc R U . . .
C204 C 0.46177(17) 0.58029(11) 0.67091(11) 0.0167(4) Uani 1 1 d . . . . .
C205 C 0.58598(18) 0.64356(11) 0.53634(11) 0.0185(4) Uani 1 1 d . . . . .
H205 H 0.606755 0.694141 0.490065 0.022 Uiso 1 1 calc R U . . .
C206 C 0.66393(17) 0.55774(11) 0.52939(10) 0.0146(4) Uani 1 1 d . . . . .
C207 C 0.62704(17) 0.48518(11) 0.60135(10) 0.0148(4) Uani 1 1 d . . . . .
C208 C 0.95894(18) 0.42802(12) 0.38775(11) 0.0192(4) Uani 1 1 d . . . . .
C209 C 0.65184(18) 0.31913(11) 0.67468(11) 0.0187(4) Uani 1 1 d . . . . .
H206 H 0.661361 0.265029 0.655150 0.022 Uiso 1 1 calc R U . . .
H207 H 0.529778 0.330395 0.697881 0.022 Uiso 1 1 calc R U . . .
C210 C 0.7754(2) 0.30284(12) 0.74495(12) 0.0286(4) Uani 1 1 d . . . . .
H208 H 0.744405 0.251757 0.792004 0.043 Uiso 1 1 calc R U . . .
H209 H 0.896225 0.290502 0.722522 0.043 Uiso 1 1 calc R U . . .
H210 H 0.764717 0.355830 0.765229 0.043 Uiso 1 1 calc R U . . .
C211 C 0.25558(19) 0.67893(11) 0.74367(11) 0.0217(4) Uani 1 1 d . . . . .
H211 H 0.129588 0.671597 0.749460 0.026 Uiso 1 1 calc R U . . .
H212 H 0.279845 0.725052 0.689832 0.026 Uiso 1 1 calc R U . . .
C212 C 0.3000(2) 0.70895(11) 0.81856(11) 0.0219(4) Uani 1 1 d . . . . .
H213 H 0.422011 0.723685 0.808935 0.026 Uiso 1 1 calc R U . . .
H214 H 0.221745 0.763294 0.822119 0.026 Uiso 1 1 calc R U . . .
C213 C 0.3364(2) 0.52010(11) 0.82126(11) 0.0213(4) Uani 1 1 d . . . . .
H215 H 0.412413 0.465323 0.817037 0.026 Uiso 1 1 calc R U . . .
H216 H 0.213307 0.507141 0.829734 0.026 Uiso 1 1 calc R U . . .
C214 C 0.38190(18) 0.54802(11) 0.89713(11) 0.0214(4) Uani 1 1 d . . . . .
H217 H 0.355405 0.501444 0.950298 0.026 Uiso 1 1 calc R U . . .
H218 H 0.508698 0.553394 0.891994 0.026 Uiso 1 1 calc R U . . .
N101 N 0.72840(17) -0.12147(10) 0.11776(10) 0.0192(3) Uani 1 1 d . . . . .
N102 N 0.64352(15) -0.08061(9) 0.27826(9) 0.0188(3) Uani 1 1 d . . . . .
N103 N 0.26816(15) 0.11493(9) 0.40277(8) 0.0159(3) Uani 1 1 d . . . . .
N104 N 0.45544(14) 0.01651(9) 0.34018(8) 0.0152(3) Uani 1 1 d . . . . .
N105 N 0.51020(15) -0.14310(9) 0.41459(9) 0.0180(3) Uani 1 1 d . . . . .
N201 N 0.27903(17) 0.63633(10) 0.90128(10) 0.0197(3) Uani 1 1 d . . . . .
N202 N 0.36190(16) 0.59292(9) 0.74164(9) 0.0201(3) Uani 1 1 d . . . . .
N203 N 0.69318(15) 0.39722(9) 0.60021(8) 0.0149(3) Uani 1 1 d . . . . .
N204 N 0.52765(15) 0.49478(9) 0.67217(9) 0.0159(3) Uani 1 1 d . . . . .
N205 N 0.48578(15) 0.65656(9) 0.60413(9) 0.0185(3) Uani 1 1 d . . . . .
O1 O 0.41920(13) 0.32839(9) 1.02725(9) 0.0328(3) Uani 1 1 d . . . . .
O2 O 0.28022(12) 0.22578(8) 0.99639(8) 0.0275(3) Uani 1 1 d . . . . .
O1W O 0.92953(15) 0.60785(10) 0.92560(10) 0.0365(4) Uani 1 1 d . . . . .
O3 O 0.73282(13) 0.22474(9) 1.01374(8) 0.0312(3) Uani 1 1 d . . . . .
O2W O 0.02528(18) 0.11003(10) 0.09340(10) 0.0369(4) Uani 1 1 d . . . . .
O4 O 0.59992(13) 0.14806(8) 0.94654(8) 0.0248(3) Uani 1 1 d . . . . .
O3W O 0.06583(15) 0.92432(10) 0.10368(10) 0.0351(4) Uani 1 1 d . . . . .
O4W O 0.00678(18) 0.68328(11) 0.09498(10) 0.0391(4) Uani 1 1 d . . . . .
O5W O 0.82847(17) 0.48891(11) 0.85075(12) 0.0365(4) Uani 1 1 d . . . . .
O101 O -0.03630(14) 0.02618(9) 0.68333(8) 0.0240(3) Uani 1 1 d . . . . .
O102 O -0.07707(14) 0.16872(8) 0.60315(8) 0.0256(3) Uani 1 1 d . . . . .
O103 O 0.17168(13) -0.09060(8) 0.62358(7) 0.0214(3) Uani 1 1 d . . . . .
O201 O 0.99228(15) 0.49844(9) 0.32051(8) 0.0269(3) Uani 1 1 d . . . . .
O202 O 1.02150(14) 0.35132(8) 0.38881(8) 0.0265(3) Uani 1 1 d . . . . .
O203 O 0.80510(14) 0.61011(8) 0.38887(8) 0.0232(3) Uani 1 1 d . . . . .
H1A H 0.829(3) 0.6319(14) 0.9440(13) 0.050(6) Uiso 1 1 d . . . . .
H1B H 0.899(3) 0.5644(16) 0.9002(15) 0.063(8) Uiso 1 1 d . . . . .
H2A H -0.062(3) 0.1417(16) 0.0604(15) 0.063(7) Uiso 1 1 d . . . . .
H2B H 0.110(3) 0.1419(15) 0.0739(15) 0.053(7) Uiso 1 1 d . . . . .
H3A H 0.069(3) 0.9858(17) 0.0969(15) 0.059(7) Uiso 1 1 d . . . . .
H3B H 0.163(3) 0.9040(14) 0.0882(14) 0.046(6) Uiso 1 1 d . . . . .
H4A H -0.085(3) 0.7011(15) 0.0610(15) 0.061(7) Uiso 1 1 d . . . . .
H4B H 0.089(3) 0.7130(16) 0.0645(15) 0.059(8) Uiso 1 1 d . . . . .
H5A H 0.854(3) 0.5026(17) 0.7961(18) 0.072(9) Uiso 1 1 d . . . . .
H5B H 0.883(3) 0.428(2) 0.8740(17) 0.089(10) Uiso 1 1 d . . . . .
H101 H 0.042(3) -0.0262(16) 0.6699(15) 0.067(7) Uiso 1 1 d . . . . .
H102 H 0.846(2) -0.1118(12) 0.1095(12) 0.036(5) Uiso 1 1 d . . . . .
H104 H 0.696(2) -0.1417(12) 0.0733(12) 0.032(5) Uiso 1 1 d . . . . .
H201 H 0.928(3) 0.5481(15) 0.3379(15) 0.061(7) Uiso 1 1 d . . . . .
H202 H 0.165(2) 0.6287(12) 0.9134(11) 0.030(5) Uiso 1 1 d . . . . .
H204 H 0.315(2) 0.6581(13) 0.9398(13) 0.036(6) 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
C1 O1 1.238(2) . ?
C1 O2 1.2601(18) . ?
C1 C2 1.552(2) . ?
C2 O4 1.2434(19) . ?
C2 O3 1.2552(18) . ?
C101 O103 1.2559(19) . ?
C101 C106 1.443(2) . ?
C101 C102 1.446(2) . ?
C102 C103 1.359(2) . ?
C102 C108 1.478(2) . ?
C103 N103 1.3487(19) . ?
C104 N104 1.3393(19) . ?
C104 N102 1.3473(19) . ?
C104 N105 1.365(2) . ?
C105 N105 1.3157(19) . ?
C105 C106 1.403(2) . ?
C106 C107 1.397(2) . ?
C107 N104 1.3270(19) . ?
C107 N103 1.3868(19) . ?
C108 O102 1.2136(19) . ?
C108 O101 1.323(2) . ?
C109 N103 1.478(2) . ?
C109 C110 1.508(2) . ?
C111 N102 1.4587(19) . ?
C111 C112 1.508(2) . ?
C112 N101 1.488(2) . ?
C113 N102 1.460(2) . ?
C113 C114 1.512(2) . ?
C114 N101 1.489(2) . ?
C201 O203 1.2622(19) . ?
C201 C202 1.437(2) . ?
C201 C206 1.438(2) . ?
C202 C203 1.366(2) . ?
C202 C208 1.484(2) . ?
C203 N203 1.3466(19) . ?
C204 N204 1.3418(19) . ?
C204 N202 1.347(2) . ?
C204 N205 1.366(2) . ?
C205 N205 1.310(2) . ?
C205 C206 1.405(2) . ?
C206 C207 1.396(2) . ?
C207 N204 1.3321(19) . ?
C207 N203 1.3872(19) . ?
C208 O202 1.2102(19) . ?
C208 O201 1.327(2) . ?
C209 N203 1.478(2) . ?
C209 C210 1.502(2) . ?
C211 N202 1.4617(19) . ?
C211 C212 1.509(2) . ?
C212 N201 1.485(2) . ?
C213 N202 1.459(2) . ?
C213 C214 1.508(2) . ?
C214 N201 1.490(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
O1 C1 O2 126.25(14) . . ?
O1 C1 C2 117.53(14) . . ?
O2 C1 C2 116.22(15) . . ?
O4 C2 O3 126.53(13) . . ?
O4 C2 C1 117.23(13) . . ?
O3 C2 C1 116.24(15) . . ?
O103 C101 C106 122.61(14) . . ?
O103 C101 C102 122.87(14) . . ?
C106 C101 C102 114.52(14) . . ?
C103 C102 C101 120.37(14) . . ?
C103 C102 C108 118.05(14) . . ?
C101 C102 C108 121.58(15) . . ?
N103 C103 C102 124.17(14) . . ?
N104 C104 N102 116.86(14) . . ?
N104 C104 N105 126.09(13) . . ?
N102 C104 N105 117.05(13) . . ?
N105 C105 C106 124.05(15) . . ?
C107 C106 C105 114.50(14) . . ?
C107 C106 C101 122.09(14) . . ?
C105 C106 C101 123.41(15) . . ?
N104 C107 N103 116.38(14) . . ?
N104 C107 C106 123.89(14) . . ?
N103 C107 C106 119.72(13) . . ?
O102 C108 O101 120.99(14) . . ?
O102 C108 C102 123.05(16) . . ?
O101 C108 C102 115.96(14) . . ?
N103 C109 C110 112.21(13) . . ?
N102 C111 C112 110.20(13) . . ?
N101 C112 C111 110.44(14) . . ?
N102 C113 C114 109.75(14) . . ?
N101 C114 C113 110.41(13) . . ?
O203 C201 C202 122.89(14) . . ?
O203 C201 C206 122.14(14) . . ?
C202 C201 C206 114.98(14) . . ?
C203 C202 C201 120.24(14) . . ?
C203 C202 C208 118.63(14) . . ?
C201 C202 C208 121.13(15) . . ?
N203 C203 C202 123.85(14) . . ?
N204 C204 N202 117.51(14) . . ?
N204 C204 N205 126.12(14) . . ?
N202 C204 N205 116.36(14) . . ?
N205 C205 C206 123.90(15) . . ?
C207 C206 C205 114.76(14) . . ?
C207 C206 C201 122.06(14) . . ?
C205 C206 C201 123.17(15) . . ?
N204 C207 N203 116.82(14) . . ?
N204 C207 C206 123.71(14) . . ?
N203 C207 C206 119.46(13) . . ?
O202 C208 O201 121.46(15) . . ?
O202 C208 C202 124.06(16) . . ?
O201 C208 C202 114.49(14) . . ?
N203 C209 C210 111.98(13) . . ?
N202 C211 C212 110.26(13) . . ?
N201 C212 C211 110.87(14) . . ?
N202 C213 C214 109.82(14) . . ?
N201 C214 C213 111.32(13) . . ?
C112 N101 C114 111.42(13) . . ?
C104 N102 C111 124.06(14) . . ?
C104 N102 C113 122.50(13) . . ?
C111 N102 C113 113.44(12) . . ?
C103 N103 C107 119.11(13) . . ?
C103 N103 C109 121.04(13) . . ?
C107 N103 C109 119.85(12) . . ?
C107 N104 C104 115.89(13) . . ?
C105 N105 C104 115.57(13) . . ?
C212 N201 C214 112.22(13) . . ?
C204 N202 C213 123.32(13) . . ?
C204 N202 C211 123.29(14) . . ?
C213 N202 C211 113.18(12) . . ?
C203 N203 C207 119.35(13) . . ?
C203 N203 C209 120.20(13) . . ?
C207 N203 C209 120.43(12) . . ?
C207 N204 C204 115.70(13) . . ?
C205 N205 C204 115.78(13) . . ?

_refine_diff_density_max         0.332
_refine_diff_density_min         -0.281
_refine_diff_density_rms         0.058

