# 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_bfm2d
_database_code_depnum_ccdc_archive 'CCDC 1941525'
loop_
_audit_author_name
_audit_author_address
'Leigh Jones'
;University of Wolverhampton 
United Kingdom
;
_audit_update_record             
;
2021-07-12 deposited with the CCDC.	2021-07-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            '[Cu1-net]'
_chemical_melting_point          ?
_chemical_formula_moiety         'C30 H30 N4 O8 Cu'
_chemical_formula_sum            'C30 H30 Cu N4 O8'
_chemical_formula_weight         638.12

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                   6.7098(2)
_cell_length_b                   21.4689(8)
_cell_length_c                   9.4280(2)
_cell_angle_alpha                90
_cell_angle_beta                 91.889(2)
_cell_angle_gamma                90
_cell_volume                     1357.38(7)
_cell_formula_units_Z            2
_cell_measurement_temperature    100.0(2)
_cell_measurement_reflns_used    9697
_cell_measurement_theta_min      2.3290
_cell_measurement_theta_max      30.6200

_exptl_crystal_description       Parallelepiped
_exptl_crystal_colour            Green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.561
_exptl_crystal_F_000             662
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.04
_exptl_absorpt_coefficient_mu    0.867
_shelx_estimated_absorpt_T_min   0.881
_shelx_estimated_absorpt_T_max   0.966
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.76834
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_process_details   
;
crysalispro 1.171.39.46 (rigaku oxford diffraction, 2018)
empirical absorption correction using spherical harmonics,
 implemented in scale3 abspack scaling algorithm.
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100.0(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'rotating-anode x-ray tube'
_diffrn_measurement_device_type  'xtalab afc12 (rcd3): kappa single'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            26867
_diffrn_reflns_av_unetI/netI     0.0210
_diffrn_reflns_av_R_equivalents  0.0487
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_theta_min         1.897
_diffrn_reflns_theta_max         25.349
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2483
_reflns_number_gt                2367
_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       'crysalispro 1.171.39.46 (rigaku od, 2018)'
_computing_cell_refinement       'crysalispro 1.171.39.46 (rigaku od, 2018)'
_computing_data_reduction        'crysalispro 1.171.39.46 (rigaku od, 2018)'
_computing_structure_solution    
'SHELXT - G.M.Sheldrick,Acta Crystallogr.A71(2015)3-8.'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    
'ORTEX - P. McArdle, J.Appl.Cryst.,1995,28,65-65.'
_computing_publication_material  
'Oscail - P. McArdle, J.Appl.Cryst.,2017,50,320-326.'
_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)+(0.0365P)²+2.1287P] 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         2483
_refine_ls_number_parameters     205
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0509
_refine_ls_R_factor_gt           0.0481
_refine_ls_wR_factor_ref         0.1113
_refine_ls_wR_factor_gt          0.1099
_refine_ls_goodness_of_fit_ref   1.303
_refine_ls_restrained_S_all      1.303
_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
Cu1 Cu 0.000000 0.500000 0.000000 0.01755(17) Uani 1 2 d S . P . .
O1 O -0.0424(3) 0.52854(10) 0.1910(2) 0.0199(5) Uani 1 1 d . . . . .
N1 N -0.3514(4) 0.53558(12) 0.0982(2) 0.0181(5) Uani 1 1 d . . . . .
C1 C -0.2261(4) 0.54083(14) 0.2079(3) 0.0170(6) Uani 1 1 d . . . . .
H2 H -0.474(5) 0.5340(15) 0.099(3) 0.016(8) Uiso 1 1 d . . . . .
O2 O -0.2799(3) 0.51312(10) -0.0289(2) 0.0193(5) Uani 1 1 d . . . . .
N2 N -0.4660(4) 0.60877(14) 0.7555(3) 0.0237(6) Uani 1 1 d . . . . .
C2 C -0.2984(4) 0.56024(14) 0.3459(3) 0.0175(6) Uani 1 1 d . . . . .
O3 O -1.0108(3) 0.62605(10) 0.9533(2) 0.0234(5) Uani 1 1 d . . . . .
H3H H -1.105429 0.629470 1.008908 0.028 Uiso 1 1 calc R U . . .
C3 C -0.4945(4) 0.57700(14) 0.3699(3) 0.0212(6) Uani 1 1 d . . . . .
H3 H -0.589355 0.577431 0.292837 0.025 Uiso 1 1 calc R U . . .
O4 O -1.0384(3) 0.68045(11) 1.2020(2) 0.0289(5) Uani 1 1 d . . . . .
C4 C -0.5538(4) 0.59304(15) 0.5039(3) 0.0211(6) Uani 1 1 d . . . . .
H4 H -0.688525 0.604490 0.517999 0.025 Uiso 1 1 calc R U . . .
C5 C -0.4165(4) 0.59255(14) 0.6195(3) 0.0200(6) Uani 1 1 d . . . . .
C6 C -0.2189(4) 0.57594(15) 0.5947(3) 0.0223(7) Uani 1 1 d . . . . .
H6 H -0.123666 0.575225 0.671463 0.027 Uiso 1 1 calc R U . . .
C7 C -0.1612(4) 0.56070(14) 0.4611(3) 0.0200(6) Uani 1 1 d . . . . .
H7 H -0.025846 0.550276 0.446297 0.024 Uiso 1 1 calc R U . . .
C8 C -0.6671(4) 0.62241(15) 0.7946(3) 0.0216(6) Uani 1 1 d . . . . .
H8A H -0.743737 0.583111 0.799387 0.026 Uiso 1 1 calc R U . . .
H8B H -0.731815 0.649092 0.720844 0.026 Uiso 1 1 calc R U . . .
C9 C -0.6712(4) 0.65510(14) 0.9361(3) 0.0196(6) Uani 1 1 d . . . . .
C10 C -0.8449(4) 0.65524(14) 1.0107(3) 0.0202(6) Uani 1 1 d . . . . .
C11 C -0.8562(5) 0.68538(15) 1.1416(3) 0.0224(6) Uani 1 1 d . . . . .
C12 C -0.6932(5) 0.71710(15) 1.1972(3) 0.0265(7) Uani 1 1 d . . . . .
H12 H -0.699397 0.737449 1.286456 0.032 Uiso 1 1 calc R U . . .
C13 C -0.5194(5) 0.71893(16) 1.1208(3) 0.0282(7) Uani 1 1 d . . . . .
H13 H -0.407207 0.741527 1.157119 0.034 Uiso 1 1 calc R U . . .
C14 C -0.5086(5) 0.68815(15) 0.9925(3) 0.0249(7) Uani 1 1 d . . . . .
H14 H -0.388371 0.689562 0.942140 0.030 Uiso 1 1 calc R U . . .
C15 C -1.0612(6) 0.70926(17) 1.3372(3) 0.0335(8) Uani 1 1 d . . . . .
H15A H -1.050783 0.754568 1.327170 0.050 Uiso 1 1 calc R U . . .
H15B H -0.956336 0.694381 1.403648 0.050 Uiso 1 1 calc R U . . .
H15C H -1.192057 0.698580 1.373456 0.050 Uiso 1 1 calc R U . . .
H2H H -0.395(6) 0.5924(17) 0.812(4) 0.026(10) 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
Cu1 O2 1.910(2) 3_565 ?
Cu1 O2 1.910(2) . ?
Cu1 O1 1.9325(19) 3_565 ?
Cu1 O1 1.9325(19) . ?
O1 C1 1.276(3) . ?
N1 C1 1.316(4) . ?
N1 O2 1.391(3) . ?
N1 H2 0.82(4) . ?
C1 C2 1.464(4) . ?
N2 C5 1.379(4) . ?
N2 C8 1.440(4) . ?
N2 H2H 0.79(4) . ?
C2 C3 1.390(4) . ?
C2 C7 1.400(4) . ?
O3 C10 1.373(4) . ?
O3 H3H 0.8400 . ?
C3 C4 1.381(4) . ?
C3 H3 0.9500 . ?
O4 C11 1.369(4) . ?
O4 C15 1.430(4) . ?
C4 C5 1.404(4) . ?
C4 H4 0.9500 . ?
C5 C6 1.400(4) . ?
C6 C7 1.370(4) . ?
C6 H6 0.9500 . ?
C7 H7 0.9500 . ?
C8 C9 1.509(4) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C10 1.381(4) . ?
C9 C14 1.392(4) . ?
C10 C11 1.398(4) . ?
C11 C12 1.377(5) . ?
C12 C13 1.392(5) . ?
C12 H12 0.9500 . ?
C13 C14 1.382(5) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 Cu1 O2 180.0 3_565 . ?
O2 Cu1 O1 84.94(8) 3_565 3_565 ?
O2 Cu1 O1 95.06(8) . 3_565 ?
O2 Cu1 O1 95.06(8) 3_565 . ?
O2 Cu1 O1 84.94(8) . . ?
O1 Cu1 O1 180.0 3_565 . ?
C1 O1 Cu1 110.73(17) . . ?
C1 N1 O2 118.5(2) . . ?
C1 N1 H2 128(2) . . ?
O2 N1 H2 111(2) . . ?
O1 C1 N1 118.7(3) . . ?
O1 C1 C2 121.3(2) . . ?
N1 C1 C2 120.1(3) . . ?
N1 O2 Cu1 107.06(15) . . ?
C5 N2 C8 123.1(3) . . ?
C5 N2 H2H 111(3) . . ?
C8 N2 H2H 118(3) . . ?
C3 C2 C7 118.3(3) . . ?
C3 C2 C1 124.1(3) . . ?
C7 C2 C1 117.6(3) . . ?
C10 O3 H3H 109.5 . . ?
C4 C3 C2 121.1(3) . . ?
C4 C3 H3 119.4 . . ?
C2 C3 H3 119.4 . . ?
C11 O4 C15 117.4(3) . . ?
C3 C4 C5 120.5(3) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
N2 C5 C6 118.6(3) . . ?
N2 C5 C4 123.2(3) . . ?
C6 C5 C4 118.2(3) . . ?
C7 C6 C5 120.9(3) . . ?
C7 C6 H6 119.6 . . ?
C5 C6 H6 119.6 . . ?
C6 C7 C2 121.1(3) . . ?
C6 C7 H7 119.5 . . ?
C2 C7 H7 119.5 . . ?
N2 C8 C9 111.4(2) . . ?
N2 C8 H8A 109.3 . . ?
C9 C8 H8A 109.3 . . ?
N2 C8 H8B 109.3 . . ?
C9 C8 H8B 109.3 . . ?
H8A C8 H8B 108.0 . . ?
C10 C9 C14 117.9(3) . . ?
C10 C9 C8 119.5(3) . . ?
C14 C9 C8 122.6(3) . . ?
O3 C10 C9 119.0(3) . . ?
O3 C10 C11 119.5(3) . . ?
C9 C10 C11 121.5(3) . . ?
O4 C11 C12 126.1(3) . . ?
O4 C11 C10 114.0(3) . . ?
C12 C11 C10 120.0(3) . . ?
C11 C12 C13 119.0(3) . . ?
C11 C12 H12 120.5 . . ?
C13 C12 H12 120.5 . . ?
C14 C13 C12 120.6(3) . . ?
C14 C13 H13 119.7 . . ?
C12 C13 H13 119.7 . . ?
C13 C14 C9 121.0(3) . . ?
C13 C14 H14 119.5 . . ?
C9 C14 H14 119.5 . . ?
O4 C15 H15A 109.5 . . ?
O4 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
O4 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

_refine_diff_density_max         0.826
_refine_diff_density_min         -0.680
_refine_diff_density_rms         0.077



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Methanol'
_exptl_crystal_preparation       'Magnetic properties'
####################################################################### 
# 
# 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_bfm3d
_database_code_depnum_ccdc_archive 'CCDC 1941526'
loop_
_audit_author_name
_audit_author_address
'Leigh Jones'
;University of Wolverhampton 
United Kingdom
;
_audit_update_record             
;
2021-07-12 deposited with the CCDC.	2021-07-22 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        ?
_chemical_name_common            '[Cu]n-2'
_chemical_melting_point          ?
_chemical_formula_moiety         'C28 H26 N4 O6 Cu (C2 H8 O2)'
_chemical_formula_sum            'C30 H34 Cu N4 O8'
_chemical_formula_weight         642.15

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                   8.61560(10)
_cell_length_b                   11.31420(10)
_cell_length_c                   14.8436(2)
_cell_angle_alpha                90
_cell_angle_beta                 100.8870(10)
_cell_angle_gamma                90
_cell_volume                     1420.89(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    100.0(1)
_cell_measurement_reflns_used    11113
_cell_measurement_theta_min      2.9830
_cell_measurement_theta_max      70.1450

_exptl_crystal_description       Parallelepiped
_exptl_crystal_colour            Green
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.501
_exptl_crystal_F_000             670
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.35
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.05
_exptl_absorpt_coefficient_mu    0.828
_shelx_estimated_absorpt_T_min   0.760
_shelx_estimated_absorpt_T_max   0.960
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_correction_T_min  0.529
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_process_details   
; 
crysalispro 1.171.40.18b (rigaku oxford diffraction, 2018) 
numerical absorption correction based on gaussian integration over 
   a multifaceted crystal model 
empirical absorption correction using spherical harmonics, 
 implemented in scale3 abspack scaling algorithm. 
;
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100.0(1)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'rotating-anode x-ray tube'
_diffrn_measurement_device_type  'xtalab afc11 (rcd3): quarter-chi single'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            12946
_diffrn_reflns_av_unetI/netI     0.0114
_diffrn_reflns_av_R_equivalents  0.0206
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_theta_min         2.279
_diffrn_reflns_theta_max         25.350
_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             2598
_reflns_number_gt                2520
_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       'crysalispro 1.171.40.18b (rigaku od, 2018)'
_computing_cell_refinement       'crysalispro 1.171.40.18b (rigaku od, 2018)'
_computing_data_reduction        'crysalispro 1.171.40.18b (rigaku od, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    
'ORTEX - P. McArdle, J.Appl.Cryst.,1995,28,65-65.'
_computing_publication_material  
'Oscail - P. McArdle, J.Appl.Cryst.,2017,50,320-326.'
_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)+(0.0876P)²+1.3725P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2598
_refine_ls_number_parameters     199
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0430
_refine_ls_R_factor_gt           0.0424
_refine_ls_wR_factor_ref         0.1406
_refine_ls_wR_factor_gt          0.1401
_refine_ls_goodness_of_fit_ref   1.138
_refine_ls_restrained_S_all      1.138
_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
Cu1 Cu 0.500000 0.500000 0.000000 0.0256(2) Uani 1 2 d S . P . .
O1 O 0.3823(2) 0.50886(13) -0.12264(12) 0.0182(4) Uani 1 1 d . . . . .
N1 N 0.2372(2) 0.55986(17) -0.11883(13) 0.0172(4) Uani 1 1 d . . . . .
H1N H 0.167998 0.571431 -0.167913 0.021 Uiso 1 1 calc R U . . .
C1 C 0.2087(3) 0.59001(18) -0.03784(15) 0.0167(5) Uani 1 1 d . . . . .
O2 O 0.31735(18) 0.57530(14) 0.03315(10) 0.0180(4) Uani 1 1 d . . . . .
N2 N -0.3949(2) 0.75632(18) 0.00058(14) 0.0215(4) Uani 1 1 d . . . . .
H2N H -0.467082 0.754628 -0.048125 0.026 Uiso 1 1 calc R U . . .
C2 C 0.0542(3) 0.63996(18) -0.02948(15) 0.0166(5) Uani 1 1 d . . . . .
O3 O -0.51081(19) 0.88422(15) 0.24364(11) 0.0209(4) Uani 1 1 d . . . . .
H3H H -0.528019 0.917545 0.292142 0.031 Uiso 1 1 calc R U . . .
C3 C 0.0225(3) 0.6620(2) 0.05727(16) 0.0194(5) Uani 1 1 d . . . . .
H3 H 0.094043 0.649339 0.104128 0.023 Uiso 1 1 calc R U . . .
O4 O 0.0413(2) 0.5409(3) -0.29159(14) 0.0435(6) Uani 1 1 d . . . . .
H4H H -0.050540 0.510555 -0.304062 0.052 Uiso 1 1 calc R U . . .
C4 C -0.1235(3) 0.7042(2) 0.06913(16) 0.0210(5) Uani 1 1 d . . . . .
H4 H -0.139922 0.718101 0.122823 0.025 Uiso 1 1 calc R U . . .
C5 C -0.2436(3) 0.72397(19) -0.00687(16) 0.0187(5) Uani 1 1 d . . . . .
C6 C -0.2091(3) 0.7060(2) -0.09497(16) 0.0208(5) Uani 1 1 d . . . . .
H6 H -0.279386 0.720534 -0.142061 0.025 Uiso 1 1 calc R U . . .
C7 C -0.0637(3) 0.6652(2) -0.10583(16) 0.0204(5) Uani 1 1 d . . . . .
H7 H -0.044936 0.655166 -0.159512 0.024 Uiso 1 1 calc R U . . .
C8 C -0.4395(3) 0.7929(2) 0.08555(17) 0.0207(5) Uani 1 1 d . . . . .
H8A H -0.400329 0.744300 0.127352 0.025 Uiso 1 1 calc R U . . .
H8B H -0.539479 0.788868 0.079140 0.025 Uiso 1 1 calc R U . . .
C9 C -0.3877(2) 0.91664(19) 0.11735(15) 0.0176(5) Uani 1 1 d . . . . .
C10 C -0.3056(3) 0.9912(2) 0.06840(18) 0.0212(5) Uani 1 1 d . . . . .
H10 H -0.282508 0.967355 0.018236 0.025 Uiso 1 1 calc R U . . .
C11 C -0.2608(3) 1.1037(2) 0.10009(17) 0.0243(5) Uani 1 1 d . . . . .
H11 H -0.209940 1.148195 0.069748 0.029 Uiso 1 1 calc R U . . .
C12 C -0.2995(3) 1.1436(2) 0.18171(17) 0.0253(5) Uani 1 1 d . . . . .
H12 H -0.271431 1.212383 0.201473 0.030 Uiso 1 1 calc R U . . .
C13 C -0.3834(3) 1.0718(2) 0.23083(17) 0.0231(5) Uani 1 1 d . . . . .
H13 H -0.407854 1.096789 0.280322 0.028 Uiso 1 1 calc R U . . .
C14 C -0.4279(3) 0.9581(2) 0.19903(16) 0.0184(5) Uani 1 1 d . . . . .
C15 C 0.1165(4) 0.5277(3) -0.3672(2) 0.0349(6) Uani 1 1 d . . . . .
H15A H 0.060714 0.560018 -0.414128 0.052 Uiso 1 1 calc R U . . .
H15B H 0.127470 0.454632 -0.377711 0.052 Uiso 1 1 calc R U . . .
H15C H 0.206846 0.560565 -0.355570 0.052 Uiso 1 1 calc R U . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Cu1 O1 1.9119(17) . ?
Cu1 O1 1.9119(17) 3_665 ?
Cu1 O2 1.9331(15) 3_665 ?
Cu1 O2 1.9331(15) . ?
O1 N1 1.387(2) . ?
N1 C1 1.317(3) . ?
N1 H1N 0.8600 . ?
C1 O2 1.281(3) . ?
C1 C2 1.473(3) . ?
N2 C5 1.378(3) . ?
N2 C8 1.446(3) . ?
N2 H2N 0.8600 . ?
C2 C3 1.388(3) . ?
C2 C7 1.401(3) . ?
O3 C14 1.352(3) . ?
O3 H3H 0.8501 . ?
C3 C4 1.387(3) . ?
C3 H3 0.8500 . ?
O4 C15 1.407(3) . ?
O4 H4H 0.8501 . ?
C4 C5 1.398(3) . ?
C4 H4 0.8500 . ?
C5 C6 1.410(3) . ?
C6 C7 1.373(3) . ?
C6 H6 0.8500 . ?
C7 H7 0.8500 . ?
C8 C9 1.517(3) . ?
C8 H8A 0.8500 . ?
C8 H8B 0.8500 . ?
C9 C10 1.390(3) . ?
C9 C14 1.403(3) . ?
C10 C11 1.387(3) . ?
C10 H10 0.8500 . ?
C11 C12 1.391(4) . ?
C11 H11 0.8500 . ?
C12 C13 1.383(3) . ?
C12 H12 0.8500 . ?
C13 C14 1.399(3) . ?
C13 H13 0.8500 . ?
C15 H15A 0.8501 . ?
C15 H15B 0.8501 . ?
C15 H15C 0.8501 . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 Cu1 O1 180.0 . 3_665 ?
O1 Cu1 O2 95.26(7) . 3_665 ?
O1 Cu1 O2 84.74(7) 3_665 3_665 ?
O1 Cu1 O2 84.74(7) . . ?
O1 Cu1 O2 95.26(7) 3_665 . ?
O2 Cu1 O2 180.0 3_665 . ?
N1 O1 Cu1 107.64(13) . . ?
C1 N1 O1 118.03(18) . . ?
C1 N1 H1N 121.0 . . ?
O1 N1 H1N 121.0 . . ?
O2 C1 N1 118.9(2) . . ?
O2 C1 C2 120.8(2) . . ?
N1 C1 C2 120.3(2) . . ?
C1 O2 Cu1 110.57(14) . . ?
C5 N2 C8 123.83(19) . . ?
C5 N2 H2N 118.1 . . ?
C8 N2 H2N 118.1 . . ?
C3 C2 C7 118.3(2) . . ?
C3 C2 C1 119.1(2) . . ?
C7 C2 C1 122.6(2) . . ?
C14 O3 H3H 109.5 . . ?
C4 C3 C2 121.4(2) . . ?
C4 C3 H3 119.3 . . ?
C2 C3 H3 119.3 . . ?
C15 O4 H4H 109.5 . . ?
C3 C4 C5 120.2(2) . . ?
C3 C4 H4 119.9 . . ?
C5 C4 H4 119.9 . . ?
N2 C5 C4 123.0(2) . . ?
N2 C5 C6 118.8(2) . . ?
C4 C5 C6 118.2(2) . . ?
C7 C6 C5 121.0(2) . . ?
C7 C6 H6 119.5 . . ?
C5 C6 H6 119.5 . . ?
C6 C7 C2 120.8(2) . . ?
C6 C7 H7 119.6 . . ?
C2 C7 H7 119.6 . . ?
N2 C8 C9 115.13(19) . . ?
N2 C8 H8A 108.5 . . ?
C9 C8 H8A 108.5 . . ?
N2 C8 H8B 108.5 . . ?
C9 C8 H8B 108.5 . . ?
H8A C8 H8B 107.5 . . ?
C10 C9 C14 118.8(2) . . ?
C10 C9 C8 123.1(2) . . ?
C14 C9 C8 118.1(2) . . ?
C11 C10 C9 121.1(2) . . ?
C11 C10 H10 119.5 . . ?
C9 C10 H10 119.5 . . ?
C10 C11 C12 119.8(2) . . ?
C10 C11 H11 120.1 . . ?
C12 C11 H11 120.1 . . ?
C13 C12 C11 120.2(2) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C12 C13 C14 120.0(2) . . ?
C12 C13 H13 120.0 . . ?
C14 C13 H13 120.0 . . ?
O3 C14 C13 122.7(2) . . ?
O3 C14 C9 117.1(2) . . ?
C13 C14 C9 120.2(2) . . ?
O4 C15 H15A 109.5 . . ?
O4 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
O4 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

_refine_diff_density_max         0.491
_refine_diff_density_min         -0.686
_refine_diff_density_rms         0.085



_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: Methanol'
