# 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 2023

####################################################################### 
# 
# 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_Li
_database_code_depnum_ccdc_archive 'CCDC 2259916'
loop_
_audit_author_name
_audit_author_address
'Waldemar Maniukiewicz'
;Institute of General and Ecological Chemistry , Lodz University of Technology
Poland
;
_audit_update_record             
;
2023-04-30 deposited with the CCDC.	2023-11-06 downloaded from the CCDC.
;

#===============================================================================

# CHEMICAL DATA

_chemical_name_systematic        1,3-dimethyl-8-(8'-quinolinyl)azaxanthine
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H12 N6 O2'
_chemical_formula_structural     ?
_chemical_formula_sum            'C15 H12 N6 O2'
_chemical_formula_iupac          ?
_chemical_formula_weight         308.31

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'

#===============================================================================

# CRYSTAL DATA

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 21'
_symmetry_Int_Tables_number      4

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

_cell_length_a                   7.4301(1)
_cell_length_b                   7.2600(1)
_cell_length_c                   12.4619(1)
_cell_angle_alpha                90
_cell_angle_beta                 99.037(1)
_cell_angle_gamma                90
_cell_volume                     663.882(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    100
_cell_measurement_reflns_used    13996
_cell_measurement_theta_min      3.566
_cell_measurement_theta_max      78.649
_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.60
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.06
_exptl_crystal_density_diffrn    1.542
_exptl_crystal_F_000             320
_exptl_absorpt_coefficient_mu    0.904
_exptl_absorpt_correction_T_min  0.609
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.123a (Rigaku Oxford Diffraction, 2022)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
#===============================================================================

# EXPERIMENTAL DATA

_diffrn_ambient_temperature      100
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, Pilatus 300K'
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            'Pilatus 300K'
_diffrn_detector_area_resol_mean 5.8140

# number of measured reflections (redundant set)
_diffrn_reflns_number            14962
_diffrn_reflns_av_R_equivalents  0.0239
_diffrn_reflns_av_unetI/netI     0.0130
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.59
_diffrn_reflns_theta_max         66.57
_diffrn_reflns_theta_full        66.57
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000

# number of unique reflections
_reflns_number_total             2313
# number of observed reflections (> n sig(I))
_reflns_number_gt                2307
_reflns_threshold_expression     I>2σ(I)

_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.41.123a (Rigaku OD, 2022)'


#===============================================================================

# REFINEMENT DATA
_refine_special_details          
;
 Refinement on F² for ALL reflections except those
 flagged by the user for potential systematic errors.
 Weighted R-factors wR and all goodnesses of fit S
 are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The
 observed criterion of F² > 2sigma(F²) is used only
 for calculating -R-factor-obs etc. and is not
 relevant to the choice of reflections for refinement.
 R-factors based on F² are statistically about twice
 as large as those based on F, and R-factors based on
 ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0317P)²+0.1594P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'shelxl-2018/3 (sheldrick 2018)'
_refine_ls_extinction_coef       0.0131(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 1027 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.01(6)
_chemical_absolute_configuration ad
_refine_ls_number_reflns         2313
_refine_ls_number_parameters     211
_refine_ls_number_restraints     1
_refine_ls_number_constraints    ?
_refine_ls_R_factor_all          0.0223
_refine_ls_R_factor_gt           0.0222
_refine_ls_wR_factor_ref         0.0585
_refine_ls_wR_factor_gt          0.0583
_refine_ls_goodness_of_fit_ref   1.078
_refine_ls_restrained_S_all      1.077
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.191
_refine_diff_density_min         -0.120
_refine_diff_density_rms         0.036

#===============================================================================

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_thermal_displace_type
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_U_iso_or_equiv
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O Uani 0.59768(17) 0.3524(2) 0.14531(10) 1.000 0.0185(4) d . . .
O2 O Uani 0.01275(16) 0.5677(2) 0.06727(10) 1.000 0.0207(4) d . . .
N1 N Uani 0.8285(2) 0.5849(2) 0.55101(12) 1.000 0.0153(4) d . . .
N2 N Uani 0.47248(19) 0.4618(2) 0.46000(11) 1.000 0.0128(4) d . . .
N3 N Uani 0.56418(19) 0.4086(2) 0.38217(12) 1.000 0.0134(4) d . . .
N4 N Uani 0.29851(19) 0.5211(2) 0.42780(12) 1.000 0.0137(4) d . . .
N5 N Uani 0.3013(2) 0.4534(2) 0.10934(12) 1.000 0.0152(4) d . . .
N6 N Uani 0.13099(19) 0.5464(2) 0.24653(12) 1.000 0.0136(4) d . . .
C1 C Uani 0.5391(2) 0.4504(2) 0.57408(13) 1.000 0.0129(5) d . . .
C2 C Uani 0.4212(2) 0.3826(2) 0.63874(15) 1.000 0.0149(5) d . . .
C3 C Uani 0.4732(2) 0.3782(3) 0.75257(15) 1.000 0.0167(5) d . . .
C4 C Uani 0.6401(3) 0.4424(3) 0.79908(14) 1.000 0.0168(5) d . . .
C5 C Uani 0.7641(2) 0.5127(2) 0.73348(14) 1.000 0.0147(5) d . . .
C6 C Uani 0.9371(2) 0.5827(3) 0.77865(15) 1.000 0.0172(5) d . . .
C7 C Uani 1.0504(2) 0.6478(3) 0.71119(16) 1.000 0.0185(6) d . . .
C8 C Uani 0.9902(2) 0.6468(3) 0.59807(16) 1.000 0.0178(5) d . . .
C9 C Uani 0.7158(2) 0.5165(2) 0.61807(14) 1.000 0.0139(5) d . . .
C10 C Uani 0.4426(2) 0.4359(3) 0.29187(14) 1.000 0.0127(5) d . . .
C11 C Uani 0.4623(2) 0.4076(3) 0.17900(14) 1.000 0.0137(5) d . . .
C12 C Uani 0.1391(2) 0.5264(3) 0.13727(14) 1.000 0.0146(5) d . . .
C13 C Uani 0.2821(2) 0.5037(3) 0.32084(14) 1.000 0.0126(5) d . . .
C14 C Uani 0.3011(3) 0.4286(3) -0.00780(14) 1.000 0.0216(6) d . . .
C15 C Uani -0.0380(2) 0.6092(3) 0.28177(15) 1.000 0.0162(5) d . . .
H2 H Uiso 0.30458 0.33860 0.60690 1.000 0.0180 c RU . .
H3 H Uiso 0.39167 0.33030 0.79713 1.000 0.0200 c RU . .
H4 H Uiso 0.67350 0.43986 0.87585 1.000 0.0200 c RU . .
H6 H Uiso 0.97407 0.58431 0.85517 1.000 0.0210 c RU . .
H7 H Uiso 1.16811 0.69303 0.73996 1.000 0.0220 c RU . .
H8 H Uiso 1.07057 0.69347 0.55241 1.000 0.0210 c RU . .
H14A H Uiso 0.19313 0.35797 -0.03917 1.000 0.0320 c RU . .
H14B H Uiso 0.41119 0.36184 -0.01915 1.000 0.0320 c RU . .
H14C H Uiso 0.29879 0.54933 -0.04313 1.000 0.0320 c RU . .
H15A H Uiso -0.03585 0.74367 0.28867 1.000 0.0240 c RU . .
H15B H Uiso -0.04856 0.55372 0.35220 1.000 0.0240 c RU . .
H15C H Uiso -0.14244 0.57218 0.22800 1.000 0.0240 c RU . .


#===============================================================================

# MOLECULAR GEOMETRY

_geom_special_details            
;
 Bond distances, angles etc. have been calculated using the
 rounded fractional coordinates. All su's are estimated
 from the variances of the (full) variance-covariance matrix.
 The cell esds are taken into account in the estimation of
 distances, angles and torsion angles
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C11 1.217(2)
O2 C12 1.215(2)
N1 C8 1.330(2)
N1 C9 1.366(2)
N2 N3 1.327(2)
N2 N4 1.362(2)
N2 C1 1.432(2)
N3 C10 1.343(2)
N4 C13 1.325(2)
N5 C11 1.403(2)
N5 C12 1.409(2)
N5 C14 1.471(2)
N6 C12 1.380(2)
N6 C13 1.374(2)
N6 C15 1.467(2)
C1 C2 1.371(2)
C1 C9 1.424(2)
C2 C3 1.411(3)
C3 C4 1.366(3)
C4 C5 1.419(3)
C5 C6 1.414(2)
C5 C9 1.427(2)
C6 C7 1.364(2)
C7 C8 1.410(3)
C10 C11 1.452(2)
C10 C13 1.389(2)
C2 H2 0.9500
C3 H3 0.9500
C4 H4 0.9500
C6 H6 0.9500
C7 H7 0.9500
C8 H8 0.9500
C14 H14A 0.9800
C14 H14B 0.9800
C14 H14C 0.9800
C15 H15A 0.9800
C15 H15B 0.9800
C15 H15C 0.9800

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C8 N1 C9 116.83(15)
N3 N2 N4 116.69(13)
N3 N2 C1 124.85(14)
N4 N2 C1 118.35(13)
N2 N3 C10 102.39(13)
N2 N4 C13 101.50(13)
C11 N5 C12 127.98(15)
C11 N5 C14 116.93(15)
C12 N5 C14 115.06(15)
C12 N6 C13 118.92(14)
C12 N6 C15 120.02(14)
C13 N6 C15 121.05(14)
N2 C1 C2 116.80(14)
N2 C1 C9 121.10(14)
C2 C1 C9 122.01(15)
C1 C2 C3 119.97(15)
C2 C3 C4 120.40(16)
C3 C4 C5 120.44(16)
C4 C5 C6 122.12(16)
C4 C5 C9 120.29(15)
C6 C5 C9 117.60(14)
C5 C6 C7 119.31(17)
C6 C7 C8 118.99(16)
N1 C8 C7 124.42(16)
N1 C9 C1 120.24(15)
N1 C9 C5 122.85(14)
C1 C9 C5 116.88(14)
N3 C10 C11 129.38(15)
N3 C10 C13 109.06(15)
C11 C10 C13 121.56(15)
O1 C11 N5 122.35(16)
O1 C11 C10 126.55(15)
N5 C11 C10 111.10(14)
O2 C12 N5 120.66(16)
O2 C12 N6 122.28(15)
N5 C12 N6 117.05(14)
N4 C13 N6 126.35(15)
N4 C13 C10 110.37(15)
N6 C13 C10 123.28(16)
C1 C2 H2 120.00
C3 C2 H2 120.00
C2 C3 H3 120.00
C4 C3 H3 120.00
C3 C4 H4 120.00
C5 C4 H4 120.00
C5 C6 H6 120.00
C7 C6 H6 120.00
C6 C7 H7 121.00
C8 C7 H7 120.00
N1 C8 H8 118.00
C7 C8 H8 118.00
N5 C14 H14A 109.00
N5 C14 H14B 109.00
N5 C14 H14C 109.00
H14A C14 H14B 109.00
H14A C14 H14C 109.00
H14B C14 H14C 109.00
N6 C15 H15A 109.00
N6 C15 H15B 109.00
N6 C15 H15C 109.00
H15A C15 H15B 109.00
H15A C15 H15C 109.00
H15B C15 H15C 109.00

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
C9 N1 C8 C7 -0.7(3)
C8 N1 C9 C1 178.95(16)
C8 N1 C9 C5 1.1(2)
N4 N2 N3 C10 0.46(19)
C1 N2 N3 C10 176.41(16)
N3 N2 N4 C13 -0.32(19)
C1 N2 N4 C13 -176.54(15)
N3 N2 C1 C2 -134.77(16)
N3 N2 C1 C9 48.7(2)
N4 N2 C1 C2 41.1(2)
N4 N2 C1 C9 -135.41(15)
N2 N3 C10 C11 178.4(2)
N2 N3 C10 C13 -0.4(2)
N2 N4 C13 N6 -179.49(19)
N2 N4 C13 C10 0.0(2)
C12 N5 C11 O1 -176.79(19)
C12 N5 C11 C10 3.0(3)
C14 N5 C11 O1 1.1(3)
C14 N5 C11 C10 -179.11(17)
C11 N5 C12 O2 176.47(19)
C11 N5 C12 N6 -4.1(3)
C14 N5 C12 O2 -1.5(3)
C14 N5 C12 N6 177.94(17)
C13 N6 C12 O2 -177.39(19)
C13 N6 C12 N5 3.2(3)
C15 N6 C12 O2 3.7(3)
C15 N6 C12 N5 -175.70(16)
C12 N6 C13 N4 177.58(19)
C12 N6 C13 C10 -1.9(3)
C15 N6 C13 N4 -3.5(3)
C15 N6 C13 C10 177.04(19)
N2 C1 C2 C3 -176.00(15)
C9 C1 C2 C3 0.5(2)
N2 C1 C9 N1 -2.9(2)
N2 C1 C9 C5 175.09(13)
C2 C1 C9 N1 -179.27(14)
C2 C1 C9 C5 -1.3(2)
C1 C2 C3 C4 0.5(3)
C2 C3 C4 C5 -0.6(3)
C3 C4 C5 C6 179.12(19)
C3 C4 C5 C9 -0.2(3)
C4 C5 C6 C7 179.78(19)
C9 C5 C6 C7 -0.9(3)
C4 C5 C9 N1 179.05(16)
C4 C5 C9 C1 1.1(2)
C6 C5 C9 N1 -0.3(2)
C6 C5 C9 C1 -178.25(15)
C5 C6 C7 C8 1.2(3)
C6 C7 C8 N1 -0.5(3)
N3 C10 C11 O1 -0.1(4)
N3 C10 C11 N5 -179.9(2)
C13 C10 C11 O1 178.5(2)
C13 C10 C11 N5 -1.2(3)
N3 C10 C13 N4 0.2(2)
N3 C10 C13 N6 179.78(18)
C11 C10 C13 N4 -178.67(18)
C11 C10 C13 N6 0.9(3)

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
#
#D   H   A   D - H  H...A   D...A    D - H...A  symm(A)
#
C7 H7 O1 0.95 2.3700 3.282(2) 160 2_756


#===END
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: DMF'
####################################################################### 
# 
# 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_P5
_database_code_depnum_ccdc_archive 'CCDC 2259918'
loop_
_audit_author_name
_audit_author_address
'Waldemar Maniukiewicz'
;Institute of General and Ecological Chemistry , Lodz University of Technology
Poland
;
_audit_update_record             
;
2023-04-30 deposited with the CCDC.	2023-11-06 downloaded from the CCDC.
;

#===============================================================================

# CHEMICAL DATA

_chemical_name_systematic        1,3-dimethyl-8-(8'-quinolinyl)azaxanthine
_chemical_formula_moiety         'C15 H12 N6 O2'
_chemical_formula_structural     ?
_chemical_formula_sum            'C15 H12 N6 O2'
_chemical_formula_iupac          ?
_chemical_formula_weight         308.31

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'

#===============================================================================

# CRYSTAL DATA

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 21'
_symmetry_Int_Tables_number      4

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

_cell_length_a                   7.4288(1)
_cell_length_b                   7.2604(1)
_cell_length_c                   12.4596(1)
_cell_angle_alpha                90
_cell_angle_beta                 99.035(1)
_cell_angle_gamma                90
_cell_volume                     663.684(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    100
_cell_measurement_reflns_used    13288
_cell_measurement_theta_min      6.0270
_cell_measurement_theta_max      78.2160
_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.080
_exptl_crystal_size_min          0.050
_exptl_crystal_density_diffrn    1.543
_exptl_crystal_F_000             320
_exptl_absorpt_coefficient_mu    0.905
_exptl_absorpt_correction_T_min  0.745
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.74a (Rigaku Oxford Diffraction, 2022)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
#===============================================================================

# EXPERIMENTAL DATA

_diffrn_ambient_temperature      100
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, Pilatus 300K'
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            'Pilatus 300K'
_diffrn_detector_area_resol_mean 5.8140

# number of measured reflections (redundant set)
_diffrn_reflns_number            14342
_diffrn_reflns_av_R_equivalents  0.0198
_diffrn_reflns_av_unetI/netI     0.0116
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         3.59
_diffrn_reflns_theta_max         66.59
_diffrn_reflns_theta_full        66.59
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000

# number of unique reflections
_reflns_number_total             2287
# number of observed reflections (> n sig(I))
_reflns_number_gt                2279
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'CrysAlisPro 1.171.42.74a (Rigaku OD, 2022)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.74a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.74a (Rigaku OD, 2022)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'

#===============================================================================

# REFINEMENT DATA

_refine_special_details          
;
 Refinement on F² for ALL reflections except those
 flagged by the user for potential systematic errors.
 Weighted R-factors wR and all goodnesses of fit S
 are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The
 observed criterion of F² > 2sigma(F²) is used only
 for calculating -R-factor-obs etc. and is not
 relevant to the choice of reflections for refinement.
 R-factors based on F² are statistically about twice
 as large as those based on F, and R-factors based on
 ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'W=1/[Σ²(FO²)+(0.0305P)²+0.1631P] WHERE P=(FO²+2FC²)/3'
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     'SHELXL-2018/3 (Sheldrick 2018)'
_refine_ls_extinction_coef       0.0060(7)
_refine_ls_extinction_expression FC^*^=KFC[1+0.001XFC²Λ³/SIN(2Θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 1004 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_chemical_absolute_configuration ad
_refine_ls_number_reflns         2287
_refine_ls_number_parameters     211
_refine_ls_number_restraints     1
_refine_ls_number_constraints    ?
_refine_ls_R_factor_all          0.0211
_refine_ls_R_factor_gt           0.0211
_refine_ls_wR_factor_ref         0.0558
_refine_ls_wR_factor_gt          0.0557
_refine_ls_goodness_of_fit_ref   1.053
_refine_ls_restrained_S_all      1.053
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.161
_refine_diff_density_min         -0.114
_refine_diff_density_rms         0.034

#===============================================================================

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_thermal_displace_type
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_U_iso_or_equiv
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O Uani 0.40226(16) 0.64753(19) 0.85478(9) 1.000 0.0185(4) d . . .
O2 O Uani 0.98727(16) 0.4324(2) 0.93284(9) 1.000 0.0206(4) d . . .
N1 N Uani 0.17141(19) 0.4150(2) 0.44901(11) 1.000 0.0153(4) d . . .
N2 N Uani 0.52753(18) 0.5383(2) 0.54003(11) 1.000 0.0127(4) d . . .
N3 N Uani 0.43580(19) 0.5915(2) 0.61791(11) 1.000 0.0134(4) d . . .
N4 N Uani 0.70149(18) 0.4790(2) 0.57231(11) 1.000 0.0137(4) d . . .
N5 N Uani 0.69867(19) 0.5466(2) 0.89071(11) 1.000 0.0152(4) d . . .
N6 N Uani 0.86900(19) 0.4537(2) 0.75349(12) 1.000 0.0136(4) d . . .
C1 C Uani 0.4608(2) 0.5496(2) 0.42601(13) 1.000 0.0132(5) d . . .
C2 C Uani 0.5788(2) 0.6173(2) 0.36126(14) 1.000 0.0152(5) d . . .
C3 C Uani 0.5267(2) 0.6218(3) 0.24750(14) 1.000 0.0169(5) d . . .
C4 C Uani 0.3599(2) 0.5575(3) 0.20092(13) 1.000 0.0169(5) d . . .
C5 C Uani 0.2359(2) 0.4874(2) 0.26644(14) 1.000 0.0147(5) d . . .
C6 C Uani 0.0628(2) 0.4173(3) 0.22136(14) 1.000 0.0172(5) d . . .
C7 C Uani -0.0505(2) 0.3522(3) 0.28887(16) 1.000 0.0186(5) d . . .
C8 C Uani 0.0099(2) 0.3532(3) 0.40202(15) 1.000 0.0175(5) d . . .
C9 C Uani 0.2842(2) 0.4834(2) 0.38197(14) 1.000 0.0140(5) d . . .
C10 C Uani 0.5574(2) 0.5641(3) 0.70822(13) 1.000 0.0128(5) d . . .
C11 C Uani 0.5377(2) 0.5922(2) 0.82103(13) 1.000 0.0137(5) d . . .
C12 C Uani 0.8609(2) 0.4736(3) 0.86280(13) 1.000 0.0147(5) d . . .
C13 C Uani 0.7180(2) 0.4963(2) 0.67927(14) 1.000 0.0126(5) d . . .
C14 C Uani 0.6988(3) 0.5716(3) 1.00795(13) 1.000 0.0214(5) d . . .
C15 C Uani 1.0380(2) 0.3909(3) 0.71825(14) 1.000 0.0161(5) d . . .
H2 H Uiso 0.69555 0.66102 0.39307 1.000 0.0180 c RU . .
H3 H Uiso 0.60816 0.66995 0.20295 1.000 0.0200 c RU . .
H4 H Uiso 0.32671 0.55971 0.12412 1.000 0.0200 c RU . .
H6 H Uiso 0.02579 0.41563 0.14483 1.000 0.0210 c RU . .
H7 H Uiso -0.16816 0.30692 0.26013 1.000 0.0220 c RU . .
H8 H Uiso -0.07054 0.30645 0.44770 1.000 0.0210 c RU . .
H14A H Uiso 0.80717 0.64166 1.03937 1.000 0.0320 c RU . .
H14B H Uiso 0.70043 0.45092 1.04327 1.000 0.0320 c RU . .
H14C H Uiso 0.58906 0.63900 1.01926 1.000 0.0320 c RU . .
H15A H Uiso 1.03656 0.25635 0.71213 1.000 0.0240 c RU . .
H15B H Uiso 1.14257 0.42916 0.77165 1.000 0.0240 c RU . .
H15C H Uiso 1.04796 0.44534 0.64744 1.000 0.0240 c RU . .


#===============================================================================

# MOLECULAR GEOMETRY

_geom_special_details            
;
 Bond distances, angles etc. have been calculated using the
 rounded fractional coordinates. All su's are estimated
 from the variances of the (full) variance-covariance matrix.
 The cell esds are taken into account in the estimation of
 distances, angles and torsion angles
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O1 C11 1.2180(19)
O2 C12 1.215(2)
N1 C8 1.328(2)
N1 C9 1.366(2)
N2 N3 1.3277(19)
N2 N4 1.3616(19)
N2 C1 1.432(2)
N3 C10 1.343(2)
N4 C13 1.325(2)
N5 C11 1.403(2)
N5 C12 1.409(2)
N5 C14 1.472(2)
N6 C12 1.380(2)
N6 C13 1.372(2)
N6 C15 1.466(2)
C1 C2 1.372(2)
C1 C9 1.424(2)
C2 C3 1.410(2)
C3 C4 1.365(2)
C4 C5 1.418(2)
C5 C6 1.415(2)
C5 C9 1.428(2)
C6 C7 1.364(2)
C7 C8 1.411(3)
C10 C11 1.450(2)
C10 C13 1.390(2)
C2 H2 0.9500
C3 H3 0.9500
C4 H4 0.9500
C6 H6 0.9500
C7 H7 0.9500
C8 H8 0.9500
C14 H14A 0.9800
C14 H14B 0.9800
C14 H14C 0.9800
C15 H15A 0.9800
C15 H15B 0.9800
C15 H15C 0.9800
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C8 N1 C9 116.86(14)
N3 N2 N4 116.64(13)
N3 N2 C1 124.83(13)
N4 N2 C1 118.42(13)
N2 N3 C10 102.38(13)
N2 N4 C13 101.58(13)
C11 N5 C12 127.96(13)
C11 N5 C14 116.93(14)
C12 N5 C14 115.09(14)
C12 N6 C13 118.92(14)
C12 N6 C15 120.01(14)
C13 N6 C15 121.06(14)
N2 C1 C2 116.76(14)
N2 C1 C9 121.17(14)
C2 C1 C9 121.96(15)
C1 C2 C3 119.97(14)
C2 C3 C4 120.46(15)
C3 C4 C5 120.42(15)
C4 C5 C6 122.20(15)
C4 C5 C9 120.30(14)
C6 C5 C9 117.50(14)
C5 C6 C7 119.35(16)
C6 C7 C8 118.95(15)
N1 C8 C7 124.47(16)
N1 C9 C1 120.24(15)
N1 C9 C5 122.86(14)
C1 C9 C5 116.88(14)
N3 C10 C11 129.38(15)
N3 C10 C13 109.09(14)
C11 C10 C13 121.52(15)
O1 C11 N5 122.30(15)
O1 C11 C10 126.55(15)
N5 C11 C10 111.14(13)
O2 C12 N5 120.65(15)
O2 C12 N6 122.32(15)
N5 C12 N6 117.02(14)
N4 C13 N6 126.38(14)
N4 C13 C10 110.31(14)
N6 C13 C10 123.31(15)
C1 C2 H2 120.00
C3 C2 H2 120.00
C2 C3 H3 120.00
C4 C3 H3 120.00
C3 C4 H4 120.00
C5 C4 H4 120.00
C5 C6 H6 120.00
C7 C6 H6 120.00
C6 C7 H7 121.00
C8 C7 H7 121.00
N1 C8 H8 118.00
C7 C8 H8 118.00
N5 C14 H14A 109.00
N5 C14 H14B 109.00
N5 C14 H14C 109.00
H14A C14 H14B 109.00
H14A C14 H14C 109.00
H14B C14 H14C 110.00
N6 C15 H15A 110.00
N6 C15 H15B 109.00
N6 C15 H15C 109.00
H15A C15 H15B 109.00
H15A C15 H15C 109.00
H15B C15 H15C 109.00
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
C9 N1 C8 C7 0.7(3)
C8 N1 C9 C1 -179.01(16)
C8 N1 C9 C5 -1.0(2)
N4 N2 N3 C10 -0.48(19)
C1 N2 N3 C10 -176.49(16)
N3 N2 N4 C13 0.32(18)
C1 N2 N4 C13 176.61(13)
N3 N2 C1 C2 134.85(16)
N3 N2 C1 C9 -48.7(2)
N4 N2 C1 C2 -41.1(2)
N4 N2 C1 C9 135.33(15)
N2 N3 C10 C11 -178.36(19)
N2 N3 C10 C13 0.4(2)
N2 N4 C13 N6 179.53(15)
N2 N4 C13 C10 -0.02(18)
C12 N5 C11 O1 176.82(17)
C12 N5 C11 C10 -3.1(2)
C14 N5 C11 O1 -1.1(2)
C14 N5 C11 C10 179.02(16)
C11 N5 C12 O2 -176.45(17)
C11 N5 C12 N6 4.2(3)
C14 N5 C12 O2 1.5(3)
C14 N5 C12 N6 -177.87(16)
C13 N6 C12 O2 177.41(17)
C13 N6 C12 N5 -3.3(2)
C15 N6 C12 O2 -3.6(3)
C15 N6 C12 N5 175.71(16)
C12 N6 C13 N4 -177.58(17)
C12 N6 C13 C10 1.9(2)
C15 N6 C13 N4 3.5(3)
C15 N6 C13 C10 -177.05(17)
N2 C1 C2 C3 176.06(15)
C9 C1 C2 C3 -0.3(2)
N2 C1 C9 N1 3.0(2)
N2 C1 C9 C5 -175.14(13)
C2 C1 C9 N1 179.22(14)
C2 C1 C9 C5 1.1(2)
C1 C2 C3 C4 -0.6(3)
C2 C3 C4 C5 0.8(3)
C3 C4 C5 C6 -179.16(19)
C3 C4 C5 C9 0.0(3)
C4 C5 C6 C7 -179.84(19)
C9 C5 C6 C7 1.0(3)
C4 C5 C9 N1 -179.01(16)
C4 C5 C9 C1 -0.9(2)
C6 C5 C9 N1 0.2(2)
C6 C5 C9 C1 178.28(15)
C5 C6 C7 C8 -1.3(3)
C6 C7 C8 N1 0.5(3)
N3 C10 C11 O1 0.1(3)
N3 C10 C11 N5 180.0(2)
C13 C10 C11 O1 -178.60(17)
C13 C10 C11 N5 1.3(2)
N3 C10 C13 N4 -0.3(2)
N3 C10 C13 N6 -179.83(15)
C11 C10 C13 N4 178.64(16)
C11 C10 C13 N6 -0.9(3)
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
#
#D   H   A   D - H  H...A   D...A    D - H...A  symm(A)
#
C7 H7 O1 0.95 2.37 3.282(2) 160 2_546


#===END
_exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: DMF'
####################################################################### 
# 
# 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_P2
_database_code_depnum_ccdc_archive 'CCDC 2259917'
loop_
_audit_author_name
_audit_author_address
'Waldemar Maniukiewicz'
;Institute of General and Ecological Chemistry , Lodz University of Technology
Poland
;
_audit_update_record             
;
2023-04-30 deposited with the CCDC.	2023-11-06 downloaded from the CCDC.
;

#===============================================================================

# CHEMICAL DATA

_chemical_name_systematic        
;
;
_chemical_formula_moiety         'C15 H17 Cu N6 O4, N O3'
_chemical_formula_structural     ?
_chemical_formula_sum            'C15 H17 Cu N7 O7'
_chemical_formula_iupac          ?
_chemical_formula_weight         470.91

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'
Cu Cu -1.9646 0.5888 ' 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'

#===============================================================================

# CRYSTAL DATA

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 21/n'
_symmetry_Int_Tables_number      14

loop_
_space_group_symop_id
_space_group_symop_operation_xyz
1 x,y,z
2 1/2-x,1/2+y,1/2-z
3 -x,-y,-z
4 1/2+x,1/2-y,1/2+z

_cell_length_a                   11.8664(1)
_cell_length_b                   7.3491(1)
_cell_length_c                   20.4216(2)
_cell_angle_alpha                90
_cell_angle_beta                 96.440(1)
_cell_angle_gamma                90
_cell_volume                     1769.68(3)
_cell_formula_units_Z            4
_cell_measurement_temperature    100
_cell_measurement_reflns_used    32894
_cell_measurement_theta_min      4.1090
_cell_measurement_theta_max      78.4750
_exptl_crystal_description       plate
_exptl_crystal_colour            brown
_exptl_crystal_size_max          0.274
_exptl_crystal_size_mid          0.056
_exptl_crystal_size_min          0.025
_exptl_crystal_density_diffrn    1.768
_exptl_crystal_F_000             964
_exptl_absorpt_coefficient_mu    2.298
_exptl_absorpt_correction_T_min  0.630
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.42.74a (Rigaku Oxford Diffraction, 2022)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
- Detector area scaling
;
#===============================================================================

# EXPERIMENTAL DATA

_diffrn_ambient_temperature      100
_diffrn_ambient_environment      N~2~
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_monochromator  mirror
_diffrn_measurement_method       'ω scans'
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, Pilatus 300K'
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_type            'Pilatus 300K'
_diffrn_detector_area_resol_mean 5.8140

# number of measured reflections (redundant set)
_diffrn_reflns_number            45745
_diffrn_reflns_av_R_equivalents  0.0353
_diffrn_reflns_av_unetI/netI     0.0116
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       24
_diffrn_reflns_theta_min         4.12
_diffrn_reflns_theta_max         67.72
_diffrn_reflns_theta_full        67.68
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000

# number of unique reflections
_reflns_number_total             3205
# number of observed reflections (> n sig(I))
_reflns_number_gt                3048
_reflns_threshold_expression     I>2σ(I)

_computing_data_collection       'CrysAlisPro 1.171.42.74a (Rigaku OD, 2022)'
_computing_cell_refinement       'CrysAlisPro 1.171.42.74a (Rigaku OD, 2022)'
_computing_data_reduction        'CrysAlisPro 1.171.42.74a (Rigaku OD, 2022)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'

#===============================================================================

# REFINEMENT DATA

_refine_special_details          
;
 Refinement on F² for ALL reflections except those
 flagged by the user for potential systematic errors.
 Weighted R-factors wR and all goodnesses of fit S
 are based on F², conventional R-factors R are based
 on F, with F set to zero for negative F². The
 observed criterion of F² > 2sigma(F²) is used only
 for calculating -R-factor-obs etc. and is not
 relevant to the choice of reflections for refinement.
 R-factors based on F² are statistically about twice
 as large as those based on F, and R-factors based on
 ALL data will be even larger.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'W=1/[Σ²(FO²)+(0.0590P)²+1.1737P] WHERE P=(FO²+2FC²)/3'
_atom_sites_solution_primary     difmap
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_number_reflns         3205
_refine_ls_number_parameters     278
_refine_ls_number_restraints     0
_refine_ls_number_constraints    ?
_refine_ls_R_factor_all          0.0312
_refine_ls_R_factor_gt           0.0302
_refine_ls_wR_factor_ref         0.0892
_refine_ls_wR_factor_gt          0.0884
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_restrained_S_all      1.070
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_diff_density_max         0.543
_refine_diff_density_min         -0.549
_refine_diff_density_rms         0.073

#===============================================================================

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_thermal_displace_type
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_occupancy
_atom_site_U_iso_or_equiv
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu Uani 0.28326(2) 0.16917(3) 0.45807(2) 1.000 0.0149(1) d . . .
O1 O Uani 0.57579(10) 0.10354(18) 0.68633(6) 1.000 0.0201(4) d . . .
O2 O Uani 0.25874(12) -0.15444(18) 0.74936(7) 1.000 0.0249(4) d . . .
O3 O Uani 0.24829(10) -0.06202(17) 0.38874(6) 1.000 0.0180(3) d . . .
O4 O Uani 0.12081(10) 0.25468(17) 0.42747(6) 1.000 0.0190(4) d . . .
N1 N Uani 0.34660(13) 0.3013(2) 0.38580(7) 1.000 0.0163(4) d . . .
N2 N Uani 0.43538(12) 0.2064(2) 0.50371(7) 1.000 0.0138(4) d . . .
N3 N Uani 0.47777(13) 0.16893(18) 0.56351(7) 1.000 0.0137(4) d . . .
N4 N Uani 0.41594(13) -0.0185(2) 0.71790(7) 1.000 0.0185(4) d . . .
N5 N Uani 0.24828(12) -0.0447(2) 0.64461(7) 1.000 0.0177(4) d . . .
N6 N Uani 0.23900(12) 0.0543(2) 0.53573(7) 1.000 0.0186(4) d . . .
C1 C Uani 0.50985(14) 0.2961(2) 0.46503(8) 1.000 0.0144(5) d . . .
C2 C Uani 0.62089(15) 0.3407(2) 0.48339(9) 1.000 0.0169(5) d . . .
C3 C Uani 0.68508(15) 0.4292(2) 0.43868(9) 1.000 0.0192(5) d . . .
C4 C Uani 0.63814(15) 0.4724(2) 0.37586(9) 1.000 0.0193(5) d . . .
C5 C Uani 0.52255(15) 0.4316(2) 0.35586(8) 1.000 0.0173(5) d . . .
O5 O Uani 0.12152(10) 0.63105(18) 0.42180(6) 1.000 0.0199(4) d . . .
C6 C Uani 0.46509(16) 0.4737(3) 0.29321(9) 1.000 0.0212(5) d . . .
O6 O Uani 0.02932(11) 0.82231(17) 0.47752(7) 1.000 0.0221(4) d . . .
C7 C Uani 0.35298(17) 0.4296(3) 0.27841(9) 1.000 0.0233(5) d . . .
O7 O Uani -0.05273(10) 0.57524(18) 0.43819(6) 1.000 0.0222(4) d . . .
C8 C Uani 0.29601(16) 0.3423(2) 0.32612(9) 1.000 0.0200(5) d . . .
C9 C Uani 0.45847(15) 0.3440(2) 0.40091(8) 1.000 0.0147(5) d . . .
C10 C Uani 0.41436(14) 0.0899(2) 0.60579(8) 1.000 0.0144(5) d . . .
C11 C Uani 0.47640(15) 0.0617(2) 0.67095(8) 1.000 0.0162(5) d . . .
C12 C Uani 0.30495(16) -0.0771(2) 0.70676(8) 1.000 0.0191(5) d . . .
C13 C Uani 0.29742(14) 0.0346(2) 0.59283(8) 1.000 0.0159(5) d . . .
C14 C Uani 0.47546(17) -0.0477(3) 0.78409(9) 1.000 0.0268(6) d . . .
C15 C Uani 0.13040(16) -0.1080(3) 0.63287(9) 1.000 0.0233(5) d . . .
N7 N Uani 0.03100(13) 0.67567(19) 0.44596(7) 1.000 0.0164(4) d . . .
H2 H Uiso 0.65498 0.31181 0.52646 1.000 0.0200 c RU . .
H3 H Uiso 0.76200 0.45963 0.45217 1.000 0.0230 c RU . .
H3A H Uiso 0.21228 -0.15741 0.39540 1.000 0.045(8) d R . .
H3B H Uiso 0.30751 -0.10138 0.37465 1.000 0.044(7) d R . .
H4 H Uiso 0.68302 0.52918 0.34601 1.000 0.0230 c RU . .
H4A H Uiso 0.07684 0.22561 0.45523 1.000 0.057(9) d R . .
H4B H Uiso 0.11698 0.36864 0.42500 1.000 0.024(6) d R . .
H6 H Uiso 0.50448 0.53288 0.26124 1.000 0.0250 c RU . .
H6N H Uiso 0.16992 0.00900 0.53205 1.000 0.035(7) c R . .
H7 H Uiso 0.31433 0.45772 0.23635 1.000 0.0280 c RU . .
H8 H Uiso 0.21840 0.31133 0.31547 1.000 0.0240 c RU . .
H14A H Uiso 0.54454 -0.11861 0.78075 1.000 0.0400 c RU . .
H14B H Uiso 0.42592 -0.11420 0.81107 1.000 0.0400 c RU . .
H14C H Uiso 0.49563 0.07012 0.80460 1.000 0.0400 c RU . .
H15A H Uiso 0.08108 -0.00585 0.61777 1.000 0.0350 c RU . .
H15B H Uiso 0.10696 -0.15691 0.67388 1.000 0.0350 c RU . .
H15C H Uiso 0.12448 -0.20336 0.59913 1.000 0.0350 c RU . .


#===============================================================================

# MOLECULAR GEOMETRY

_geom_special_details            
;
 Bond distances, angles etc. have been calculated using the
 rounded fractional coordinates. All su's are estimated
 from the variances of the (full) variance-covariance matrix.
 The cell esds are taken into account in the estimation of
 distances, angles and torsion angles
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cu1 O3 2.2207(13)
Cu1 O4 2.0570(12)
Cu1 N1 1.9837(15)
Cu1 N2 1.9557(15)
Cu1 N6 1.9211(15)
O1 C11 1.225(2)
O2 C12 1.220(2)
N1 C8 1.331(2)
N1 C9 1.365(2)
N2 N3 1.297(2)
N2 C1 1.413(2)
N3 C10 1.340(2)
O3 H3A 0.8400
O3 H3B 0.8400
N4 C14 1.469(2)
N4 C11 1.391(2)
N4 C12 1.380(2)
O4 H4A 0.8400
O4 H4B 0.8400
N5 C15 1.468(2)
N5 C12 1.389(2)
N5 C13 1.392(2)
N6 C13 1.296(2)
C1 C9 1.425(2)
C1 C2 1.369(2)
C2 C3 1.412(2)
C3 C4 1.377(3)
C4 C5 1.419(3)
C5 C6 1.415(2)
C5 C9 1.413(2)
O5 N7 1.2742(19)
O6 N7 1.2570(19)
N6 H6N 0.8800
C6 C7 1.370(3)
C7 C8 1.402(3)
O7 N7 1.2336(19)
C10 C13 1.442(2)
C10 C11 1.462(2)
C2 H2 0.9500
C3 H3 0.9500
C4 H4 0.9500
C6 H6 0.9500
C7 H7 0.9500
C8 H8 0.9500
C14 H14C 0.9800
C14 H14A 0.9800
C14 H14B 0.9800
C15 H15A 0.9800
C15 H15B 0.9800
C15 H15C 0.9800

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
O3 Cu1 O4 86.46(5)
O3 Cu1 N1 87.68(5)
O3 Cu1 N2 120.49(5)
O3 Cu1 N6 98.12(5)
O4 Cu1 N1 92.57(6)
O4 Cu1 N2 152.31(6)
O4 Cu1 N6 92.95(6)
N1 Cu1 N2 83.08(6)
N1 Cu1 N6 172.23(6)
N2 Cu1 N6 89.50(6)
Cu1 N1 C8 128.49(13)
Cu1 N1 C9 112.60(11)
C8 N1 C9 118.82(15)
Cu1 N2 N3 131.21(12)
Cu1 N2 C1 113.62(11)
N3 N2 C1 115.13(14)
N2 N3 C10 120.82(15)
Cu1 O3 H3A 127.00
Cu1 O3 H3B 112.00
H3A O3 H3B 103.00
C11 N4 C12 125.10(14)
C11 N4 C14 117.65(15)
C12 N4 C14 117.23(14)
Cu1 O4 H4A 110.00
Cu1 O4 H4B 111.00
H4A O4 H4B 105.00
C12 N5 C13 124.41(15)
C12 N5 C15 116.73(14)
C13 N5 C15 118.78(14)
Cu1 N6 C13 128.58(12)
N2 C1 C9 113.52(14)
C2 C1 C9 119.47(15)
N2 C1 C2 127.01(15)
C1 C2 C3 120.39(16)
C2 C3 C4 121.17(16)
C3 C4 C5 119.77(16)
C4 C5 C9 118.85(15)
C4 C5 C6 124.50(16)
C6 C5 C9 116.65(16)
Cu1 N6 H6N 116.00
C5 C6 C7 120.36(17)
C13 N6 H6N 116.00
C6 C7 C8 119.15(17)
N1 C8 C7 122.46(17)
N1 C9 C1 117.12(15)
N1 C9 C5 122.57(15)
C1 C9 C5 120.32(16)
N3 C10 C11 112.73(15)
N3 C10 C13 127.05(15)
C11 C10 C13 120.22(14)
O1 C11 N4 119.05(15)
N4 C11 C10 116.20(15)
O1 C11 C10 124.75(15)
O2 C12 N5 121.43(17)
N4 C12 N5 116.91(14)
O2 C12 N4 121.66(16)
N5 C13 C10 117.09(14)
N6 C13 C10 122.71(15)
N5 C13 N6 120.20(15)
C1 C2 H2 120.00
C3 C2 H2 120.00
C2 C3 H3 119.00
C4 C3 H3 119.00
C3 C4 H4 120.00
C5 C4 H4 120.00
C5 C6 H6 120.00
C7 C6 H6 120.00
C6 C7 H7 120.00
C8 C7 H7 120.00
O5 N7 O7 119.87(14)
O6 N7 O7 121.34(15)
O5 N7 O6 118.80(14)
C7 C8 H8 119.00
N1 C8 H8 119.00
N4 C14 H14B 109.00
H14A C14 H14C 109.00
N4 C14 H14C 109.00
H14A C14 H14B 109.00
N4 C14 H14A 109.00
H14B C14 H14C 109.00
N5 C15 H15C 109.00
H15A C15 H15C 109.00
H15B C15 H15C 109.00
H15A C15 H15B 109.00
N5 C15 H15A 109.00
N5 C15 H15B 109.00

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
O3 Cu1 N1 C8 57.69(15)
O3 Cu1 N1 C9 -118.70(11)
O4 Cu1 N1 C8 -28.67(15)
O4 Cu1 N1 C9 154.95(11)
N2 Cu1 N1 C8 178.78(15)
N2 Cu1 N1 C9 2.40(11)
O3 Cu1 N2 N3 -101.44(15)
O3 Cu1 N2 C1 81.34(12)
O4 Cu1 N2 N3 93.08(18)
O4 Cu1 N2 C1 -84.13(16)
N1 Cu1 N2 N3 175.38(16)
N1 Cu1 N2 C1 -1.84(11)
N6 Cu1 N2 N3 -2.30(15)
N6 Cu1 N2 C1 -179.52(12)
O3 Cu1 N6 C13 124.91(15)
O4 Cu1 N6 C13 -148.25(15)
N2 Cu1 N6 C13 4.16(15)
Cu1 N1 C8 C7 -176.93(14)
C9 N1 C8 C7 -0.7(2)
Cu1 N1 C9 C1 -2.56(18)
Cu1 N1 C9 C5 177.35(12)
C8 N1 C9 C1 -179.33(14)
C8 N1 C9 C5 0.6(2)
Cu1 N2 N3 C10 0.4(2)
C1 N2 N3 C10 177.59(14)
Cu1 N2 C1 C2 -179.97(12)
Cu1 N2 C1 C9 0.98(17)
N3 N2 C1 C2 2.3(2)
N3 N2 C1 C9 -176.71(14)
N2 N3 C10 C11 -178.96(14)
N2 N3 C10 C13 0.9(2)
C12 N4 C11 O1 -177.97(15)
C12 N4 C11 C10 2.1(2)
C14 N4 C11 O1 0.3(2)
C14 N4 C11 C10 -179.58(15)
C11 N4 C12 O2 176.37(16)
C11 N4 C12 N5 -3.4(2)
C14 N4 C12 O2 -2.0(2)
C14 N4 C12 N5 178.34(15)
C13 N5 C12 O2 -176.72(15)
C13 N5 C12 N4 3.0(2)
C15 N5 C12 O2 0.0(2)
C15 N5 C12 N4 179.73(15)
C12 N5 C13 N6 177.75(15)
C12 N5 C13 C10 -1.5(2)
C15 N5 C13 N6 1.1(2)
C15 N5 C13 C10 -178.15(15)
Cu1 N6 C13 N5 176.55(11)
Cu1 N6 C13 C10 -4.3(2)
N2 C1 C2 C3 179.34(15)
C9 C1 C2 C3 -1.7(2)
N2 C1 C9 N1 1.1(2)
N2 C1 C9 C5 -178.84(14)
C2 C1 C9 N1 -178.06(14)
C2 C1 C9 C5 2.0(2)
C1 C2 C3 C4 -0.1(2)
C2 C3 C4 C5 1.5(2)
C3 C4 C5 C6 178.45(17)
C3 C4 C5 C9 -1.1(2)
C4 C5 C6 C7 -179.71(18)
C9 C5 C6 C7 -0.1(3)
C4 C5 C9 N1 179.45(15)
C4 C5 C9 C1 -0.6(2)
C6 C5 C9 N1 -0.2(2)
C6 C5 C9 C1 179.77(15)
C5 C6 C7 C8 0.0(3)
C6 C7 C8 N1 0.5(3)
N3 C10 C11 O1 -0.4(2)
N3 C10 C11 N4 179.48(14)
C13 C10 C11 O1 179.68(15)
C13 C10 C11 N4 -0.4(2)
N3 C10 C13 N5 -179.74(15)
N3 C10 C13 N6 1.1(3)
C11 C10 C13 N5 0.1(2)
C11 C10 C13 N6 -179.08(15)

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
#
#D   H   A   D - H  H...A   D...A    D - H...A  symm(A)
#
O3 H3A O5 0.8400 2.0000 2.8345(18) 173.00 1_545
O3 H3B O1 0.8400 1.9600 2.7421(17) 154.00 3_656
O4 H4A O6 0.8400 2.0000 2.8344(18) 175.00 3_566
O4 H4B O5 0.8400 1.9300 2.7685(18) 175.00 .
N6 H6N O6 0.8800 2.3400 3.138(2) 150.00 1_545


#===END
_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Ethanol'
