# 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 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_D-1
_database_code_depnum_ccdc_archive 'CCDC 2041015'
_audit_update_record             
;
2021-09-13 deposited with the CCDC.	2021-09-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H18 Cu N2 O5, 2(H2 O)'
_chemical_formula_sum            'C14 H22 Cu N2 O7'
_chemical_formula_weight         393.89

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   11.39160(13)
_cell_length_b                   5.69116(6)
_cell_length_c                   12.43561(14)
_cell_angle_alpha                90
_cell_angle_beta                 102.1946(11)
_cell_angle_gamma                90
_cell_volume                     788.026(15)
_cell_formula_units_Z            2
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    13654
_cell_measurement_theta_min      3.6250
_cell_measurement_theta_max      73.2270

_exptl_crystal_description       rod
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.660
_exptl_crystal_F_000             410
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.400
_exptl_crystal_size_mid          0.120
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    2.339
_shelx_estimated_absorpt_T_min   0.455
_shelx_estimated_absorpt_T_max   0.800
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.750
_exptl_absorpt_correction_T_max  0.791
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.80a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 10
_diffrn_reflns_number            16668
_diffrn_reflns_av_unetI/netI     0.0201
_diffrn_reflns_av_R_equivalents  0.0361
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.636
_diffrn_reflns_theta_max         74.311
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.980
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.980
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.948
_diffrn_reflns_point_group_measured_fraction_full 0.987
_reflns_number_total             3195
_reflns_number_gt                3020
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.749
_reflns_Friedel_fraction_max     0.909
_reflns_Friedel_fraction_full    0.972

_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 1.171.40.80a (Rigaku OD, 2020)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.80a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.80a (Rigaku OD, 2020)'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXL-2014 (Sheldrick, 2014)'
_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)+(0.0287P)²+0.4521P] 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     SHELXL
_refine_ls_extinction_coef       0.0059(5)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 1289 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.010(12)
_chemical_absolute_configuration rmad
_refine_ls_number_reflns         3029
_refine_ls_number_parameters     231
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0215
_refine_ls_R_factor_gt           0.0214
_refine_ls_wR_factor_ref         0.0561
_refine_ls_wR_factor_gt          0.0561
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_restrained_S_all      1.021
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.10093(3) 0.66525(6) 0.67156(3) 0.01396(12) Uani 1 1 d . . . . .
C1 C 0.2918(2) 0.3918(5) 0.6057(2) 0.0188(5) Uani 1 1 d . . . . .
H1A H 0.2871 0.2200 0.6166 0.023 Uiso 1 1 calc R U . . .
H1B H 0.3271 0.4660 0.6773 0.023 Uiso 1 1 calc R U . . .
C2 C 0.3664(2) 0.4473(6) 0.5211(2) 0.0239(6) Uani 1 1 d . . . . .
H2A H 0.3556 0.3260 0.4628 0.029 Uiso 1 1 calc R U . . .
H2B H 0.4528 0.4594 0.5559 0.029 Uiso 1 1 calc R U . . .
C3 C 0.3164(2) 0.6834(6) 0.4751(2) 0.0227(6) Uani 1 1 d . . . . .
H3A H 0.3344 0.7129 0.4018 0.027 Uiso 1 1 calc R U . . .
H3B H 0.3494 0.8136 0.5252 0.027 Uiso 1 1 calc R U . . .
C4 C 0.18024(19) 0.6552(6) 0.46727(18) 0.0155(5) Uani 1 1 d . . . . .
H4 H 0.1426 0.5817 0.3952 0.019 Uiso 1 1 calc R U . . .
C5 C 0.1197(2) 0.8891(5) 0.4789(2) 0.0143(5) Uani 1 1 d . . . . .
C6 C 0.1162(2) 0.7307(5) 0.8998(2) 0.0153(6) Uani 1 1 d . . . . .
H6 H 0.0599 0.7592 0.9502 0.018 Uiso 1 1 calc R U . . .
C7 C 0.1176(2) 0.4682(5) 0.8753(2) 0.0159(5) Uani 1 1 d . . . . .
C8 C 0.2425(2) 0.8106(5) 0.9578(2) 0.0175(5) Uani 1 1 d . . . . .
H8A H 0.2389 0.9799 0.9752 0.021 Uiso 1 1 calc R U . . .
H8B H 0.2650 0.7252 1.0285 0.021 Uiso 1 1 calc R U . . .
C9 C 0.3412(2) 0.7750(5) 0.8946(2) 0.0172(5) Uani 1 1 d . . . . .
C10 C 0.3660(3) 0.9469(5) 0.8227(2) 0.0210(6) Uani 1 1 d . . . . .
H10 H 0.3177 1.0844 0.8105 0.025 Uiso 1 1 calc R U . . .
C11 C 0.4608(2) 0.9205(6) 0.7685(2) 0.0231(6) Uani 1 1 d . . . . .
H11 H 0.4766 1.0391 0.7197 0.028 Uiso 1 1 calc R U . . .
C12 C 0.5317(2) 0.7205(5) 0.7860(2) 0.0211(6) Uani 1 1 d . . . . .
C13 C 0.5084(2) 0.5477(5) 0.8568(2) 0.0216(6) Uani 1 1 d . . . . .
H13 H 0.5566 0.4101 0.8685 0.026 Uiso 1 1 calc R U . . .
C14 C 0.4138(2) 0.5760(5) 0.9110(2) 0.0190(5) Uani 1 1 d . . . . .
H14 H 0.3986 0.4573 0.9601 0.023 Uiso 1 1 calc R U . . .
N1 N 0.16949(19) 0.4916(4) 0.55905(17) 0.0137(4) Uani 1 1 d . . . . .
H1 H 0.1140 0.3602 0.5287 0.016 Uiso 1 1 calc R U . . .
N2 N 0.0707(2) 0.8582(4) 0.79516(18) 0.0164(5) Uani 1 1 d . . . . .
H2C H 0.1087 0.9991 0.7963 0.020 Uiso 1 1 calc R U . . .
H2D H -0.0094 0.8855 0.7867 0.020 Uiso 1 1 calc R U . . .
O1 O 0.08714(16) 0.9301(3) 0.56954(14) 0.0166(4) Uani 1 1 d . . . . .
O2 O 0.10612(17) 1.0344(4) 0.40230(15) 0.0194(4) Uani 1 1 d . . . . .
O3 O 0.11783(17) 0.4061(4) 0.77616(15) 0.0184(4) Uani 1 1 d . . . . .
O4 O 0.12275(19) 0.3267(4) 0.95176(16) 0.0227(4) Uani 1 1 d . . . . .
O5 O 0.62347(17) 0.7032(4) 0.73043(17) 0.0286(5) Uani 1 1 d . . . . .
H5 H 0.6611 0.5772 0.7477 0.043 Uiso 1 1 calc R U . . .
O6 O 0.8318(2) 0.9690(4) 0.83381(18) 0.0254(5) Uani 1 1 d . . . . .
H6A H 0.848(3) 0.927(8) 0.906(4) 0.038 Uiso 1 1 d . U . . .
H6B H 0.780(4) 0.878(9) 0.800(4) 0.038 Uiso 1 1 d . U . . .
O7 O 0.8074(2) 0.4331(5) 0.7855(2) 0.0302(5) Uani 1 1 d . . . . .
H7A H 0.834(4) 0.452(9) 0.733(4) 0.045 Uiso 1 1 d . U . . .
H7B H 0.811(4) 0.302(9) 0.802(4) 0.045 Uiso 1 1 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
Cu1 O3 1.949(2) . ?
Cu1 O1 1.9549(19) . ?
Cu1 N2 1.978(2) . ?
Cu1 N1 2.002(2) . ?
C1 N1 1.503(3) . ?
C1 C2 1.520(4) . ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C2 C3 1.523(4) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.542(3) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 N1 1.498(3) . ?
C4 C5 1.521(4) . ?
C4 H4 1.0000 . ?
C5 O2 1.246(3) . ?
C5 O1 1.279(3) . ?
C6 N2 1.484(3) . ?
C6 C7 1.525(4) . ?
C6 C8 1.535(4) . ?
C6 H6 1.0000 . ?
C7 O4 1.238(3) . ?
C7 O3 1.283(3) . ?
C8 C9 1.515(4) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C14 1.391(4) . ?
C9 C10 1.394(4) . ?
C10 C11 1.397(4) . ?
C10 H10 0.9500 . ?
C11 C12 1.386(4) . ?
C11 H11 0.9500 . ?
C12 O5 1.374(3) . ?
C12 C13 1.382(4) . ?
C13 C14 1.397(4) . ?
C13 H13 0.9500 . ?
C14 H14 0.9500 . ?
N1 H1 1.0000 . ?
N2 H2C 0.9100 . ?
N2 H2D 0.9100 . ?
O5 H5 0.8400 . ?
O6 H6A 0.90(4) . ?
O6 H6B 0.83(5) . ?
O7 H7A 0.79(5) . ?
O7 H7B 0.77(5) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 Cu1 O1 178.45(9) . . ?
O3 Cu1 N2 84.86(9) . . ?
O1 Cu1 N2 94.18(9) . . ?
O3 Cu1 N1 95.43(9) . . ?
O1 Cu1 N1 85.23(8) . . ?
N2 Cu1 N1 167.23(9) . . ?
N1 C1 C2 105.2(2) . . ?
N1 C1 H1A 110.7 . . ?
C2 C1 H1A 110.7 . . ?
N1 C1 H1B 110.7 . . ?
C2 C1 H1B 110.7 . . ?
H1A C1 H1B 108.8 . . ?
C1 C2 C3 102.9(2) . . ?
C1 C2 H2A 111.2 . . ?
C3 C2 H2A 111.2 . . ?
C1 C2 H2B 111.2 . . ?
C3 C2 H2B 111.2 . . ?
H2A C2 H2B 109.1 . . ?
C2 C3 C4 102.9(3) . . ?
C2 C3 H3A 111.2 . . ?
C4 C3 H3A 111.2 . . ?
C2 C3 H3B 111.2 . . ?
C4 C3 H3B 111.2 . . ?
H3A C3 H3B 109.1 . . ?
N1 C4 C5 111.08(19) . . ?
N1 C4 C3 105.1(2) . . ?
C5 C4 C3 111.9(3) . . ?
N1 C4 H4 109.6 . . ?
C5 C4 H4 109.6 . . ?
C3 C4 H4 109.6 . . ?
O2 C5 O1 122.7(2) . . ?
O2 C5 C4 119.5(2) . . ?
O1 C5 C4 117.7(2) . . ?
N2 C6 C7 108.7(2) . . ?
N2 C6 C8 112.7(2) . . ?
C7 C6 C8 109.6(2) . . ?
N2 C6 H6 108.6 . . ?
C7 C6 H6 108.6 . . ?
C8 C6 H6 108.6 . . ?
O4 C7 O3 123.3(3) . . ?
O4 C7 C6 119.0(2) . . ?
O3 C7 C6 117.7(2) . . ?
C9 C8 C6 116.2(2) . . ?
C9 C8 H8A 108.2 . . ?
C6 C8 H8A 108.2 . . ?
C9 C8 H8B 108.2 . . ?
C6 C8 H8B 108.2 . . ?
H8A C8 H8B 107.4 . . ?
C14 C9 C10 118.1(3) . . ?
C14 C9 C8 121.0(2) . . ?
C10 C9 C8 120.8(3) . . ?
C9 C10 C11 121.1(3) . . ?
C9 C10 H10 119.5 . . ?
C11 C10 H10 119.5 . . ?
C12 C11 C10 119.8(3) . . ?
C12 C11 H11 120.1 . . ?
C10 C11 H11 120.1 . . ?
O5 C12 C13 122.6(3) . . ?
O5 C12 C11 117.4(3) . . ?
C13 C12 C11 120.1(2) . . ?
C12 C13 C14 119.8(3) . . ?
C12 C13 H13 120.1 . . ?
C14 C13 H13 120.1 . . ?
C9 C14 C13 121.2(3) . . ?
C9 C14 H14 119.4 . . ?
C13 C14 H14 119.4 . . ?
C4 N1 C1 108.11(19) . . ?
C4 N1 Cu1 109.42(17) . . ?
C1 N1 Cu1 112.53(15) . . ?
C4 N1 H1 108.9 . . ?
C1 N1 H1 108.9 . . ?
Cu1 N1 H1 108.9 . . ?
C6 N2 Cu1 108.90(16) . . ?
C6 N2 H2C 109.9 . . ?
Cu1 N2 H2C 109.9 . . ?
C6 N2 H2D 109.9 . . ?
Cu1 N2 H2D 109.9 . . ?
H2C N2 H2D 108.3 . . ?
C5 O1 Cu1 115.62(17) . . ?
C7 O3 Cu1 114.36(18) . . ?
C12 O5 H5 109.5 . . ?
H6A O6 H6B 108(4) . . ?
H7A O7 H7B 110(5) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 34.0(3) . . . . ?
C1 C2 C3 C4 -39.7(3) . . . . ?
C2 C3 C4 N1 30.8(3) . . . . ?
C2 C3 C4 C5 151.5(2) . . . . ?
N1 C4 C5 O2 -170.6(2) . . . . ?
C3 C4 C5 O2 72.3(3) . . . . ?
N1 C4 C5 O1 11.1(3) . . . . ?
C3 C4 C5 O1 -106.0(3) . . . . ?
N2 C6 C7 O4 -161.8(2) . . . . ?
C8 C6 C7 O4 74.7(3) . . . . ?
N2 C6 C7 O3 20.7(3) . . . . ?
C8 C6 C7 O3 -102.9(3) . . . . ?
N2 C6 C8 C9 -61.2(3) . . . . ?
C7 C6 C8 C9 60.0(3) . . . . ?
C6 C8 C9 C14 -95.1(3) . . . . ?
C6 C8 C9 C10 88.3(3) . . . . ?
C14 C9 C10 C11 0.1(4) . . . . ?
C8 C9 C10 C11 176.8(3) . . . . ?
C9 C10 C11 C12 0.0(4) . . . . ?
C10 C11 C12 O5 179.9(2) . . . . ?
C10 C11 C12 C13 0.2(4) . . . . ?
O5 C12 C13 C14 179.9(3) . . . . ?
C11 C12 C13 C14 -0.4(4) . . . . ?
C10 C9 C14 C13 -0.4(4) . . . . ?
C8 C9 C14 C13 -177.0(3) . . . . ?
C12 C13 C14 C9 0.6(4) . . . . ?
C5 C4 N1 C1 -131.2(2) . . . . ?
C3 C4 N1 C1 -10.0(3) . . . . ?
C5 C4 N1 Cu1 -8.3(2) . . . . ?
C3 C4 N1 Cu1 112.9(2) . . . . ?
C2 C1 N1 C4 -14.9(3) . . . . ?
C2 C1 N1 Cu1 -135.81(19) . . . . ?
C7 C6 N2 Cu1 -24.8(2) . . . . ?
C8 C6 N2 Cu1 96.9(2) . . . . ?
O2 C5 O1 Cu1 173.59(19) . . . . ?
C4 C5 O1 Cu1 -8.1(3) . . . . ?
O4 C7 O3 Cu1 177.1(2) . . . . ?
C6 C7 O3 Cu1 -5.5(3) . . . . ?

_refine_diff_density_max         0.195
_refine_diff_density_min         -0.220
_refine_diff_density_rms         0.044

_shelxl_version_number           2014-3

####################################################################### 
# 
# 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_L-1
_audit_block_doi                 10.5517/ccdc.csd.cc26f820
_database_code_depnum_ccdc_archive 'CCDC 2038531'
loop_
_audit_author_name
_audit_author_address
L
;new j chem
China
;
_audit_update_record             
;
2021-09-13 deposited with the CCDC.	2021-09-24 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2014
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C14 H18 Cu N2 O5, 2(H2 O)'
_chemical_formula_sum            'C14 H22 Cu N2 O7'
_chemical_formula_weight         393.89

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'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_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'

_cell_length_a                   11.3860(2)
_cell_length_b                   5.69090(10)
_cell_length_c                   12.4062(2)
_cell_angle_alpha                90
_cell_angle_beta                 102.327(2)
_cell_angle_gamma                90
_cell_volume                     785.35(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    10977
_cell_measurement_theta_min      3.6470
_cell_measurement_theta_max      71.3650

_exptl_crystal_description       rod
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.666
_exptl_crystal_F_000             410
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.6
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.35
_exptl_absorpt_coefficient_mu    2.347
_shelx_estimated_absorpt_T_min   ?
_shelx_estimated_absorpt_T_max   ?
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.373
_exptl_absorpt_correction_T_max  0.440
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.80a (Rigaku Oxford Diffraction, 2020)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     1.54184
_diffrn_radiation_type           CuK\a
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean 10
_diffrn_reflns_number            17304
_diffrn_reflns_av_unetI/netI     0.0288
_diffrn_reflns_av_R_equivalents  0.0519
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_theta_min         3.647
_diffrn_reflns_theta_max         71.523
_diffrn_reflns_theta_full        67.684
_diffrn_measured_fraction_theta_max 0.976
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.976
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.950
_diffrn_reflns_point_group_measured_fraction_full 0.986
_reflns_number_total             3047
_reflns_number_gt                2862
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.759
_reflns_Friedel_fraction_max     0.919
_reflns_Friedel_fraction_full    0.972

_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 1.171.40.80a (Rigaku OD, 2020)'
_computing_cell_refinement       'CrysAlisPro 1.171.40.80a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.80a (Rigaku OD, 2020)'
_computing_structure_solution    'SHELXL-2014 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2014 (Sheldrick, 2014)'
_computing_molecular_graphics    'SHELXL-2014 (Sheldrick, 2014)'
_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)+(0.0293P)²+0.3901P] 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     SHELXL
_refine_ls_extinction_coef       0.0023(4)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_abs_structure_details 
;
 Flack x determined using 1227 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.025(15)
_chemical_absolute_configuration rmad
_refine_ls_number_reflns         2896
_refine_ls_number_parameters     231
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0229
_refine_ls_R_factor_gt           0.0227
_refine_ls_wR_factor_ref         0.0591
_refine_ls_wR_factor_gt          0.0587
_refine_ls_goodness_of_fit_ref   1.041
_refine_ls_restrained_S_all      1.041
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.10051(3) 0.33609(6) 0.67161(3) 0.01020(13) Uani 1 1 d . . . . .
C1 C 0.2917(2) 0.6087(6) 0.6059(2) 0.0147(6) Uani 1 1 d . . . . .
H1A H 0.3262 0.5361 0.6763 0.018 Uiso 1 1 calc R U . . .
H1B H 0.2869 0.7770 0.6166 0.018 Uiso 1 1 calc R U . . .
C2 C 0.3671(3) 0.5539(6) 0.5213(2) 0.0165(6) Uani 1 1 d . . . . .
H2A H 0.4517 0.5423 0.5558 0.020 Uiso 1 1 calc R U . . .
H2B H 0.3564 0.6725 0.4638 0.020 Uiso 1 1 calc R U . . .
C3 C 0.3169(2) 0.3171(6) 0.4754(2) 0.0163(6) Uani 1 1 d . . . . .
H3A H 0.3494 0.1900 0.5250 0.020 Uiso 1 1 calc R U . . .
H3B H 0.3347 0.2876 0.4036 0.020 Uiso 1 1 calc R U . . .
C4 C 0.1803(2) 0.3443(6) 0.46704(19) 0.0113(5) Uani 1 1 d . . . . .
H4 H 0.1435 0.4158 0.3960 0.014 Uiso 1 1 calc R U . . .
C5 C 0.1198(2) 0.1109(5) 0.4789(2) 0.0113(6) Uani 1 1 d . . . . .
C6 C 0.1159(3) 0.2718(5) 0.9004(2) 0.0111(6) Uani 1 1 d . . . . .
H6 H 0.0609 0.2436 0.9500 0.013 Uiso 1 1 calc R U . . .
C7 C 0.1171(2) 0.5339(5) 0.8760(2) 0.0118(6) Uani 1 1 d . . . . .
C8 C 0.2426(2) 0.1918(5) 0.9584(2) 0.0120(6) Uani 1 1 d . . . . .
H8A H 0.2650 0.2754 1.0279 0.014 Uiso 1 1 calc R U . . .
H8B H 0.2392 0.0259 0.9755 0.014 Uiso 1 1 calc R U . . .
C9 C 0.3410(3) 0.2275(5) 0.8950(2) 0.0122(6) Uani 1 1 d . . . . .
C10 C 0.3659(3) 0.0558(5) 0.8226(2) 0.0148(6) Uani 1 1 d . . . . .
H10 H 0.3183 -0.0784 0.8103 0.018 Uiso 1 1 calc R U . . .
C11 C 0.4603(3) 0.0809(6) 0.7684(2) 0.0155(6) Uani 1 1 d . . . . .
H11 H 0.4757 -0.0357 0.7207 0.019 Uiso 1 1 calc R U . . .
C12 C 0.5315(2) 0.2812(5) 0.7859(2) 0.0143(6) Uani 1 1 d . . . . .
C13 C 0.5085(3) 0.4546(5) 0.8572(2) 0.0145(6) Uani 1 1 d . . . . .
H13 H 0.5559 0.5891 0.8687 0.017 Uiso 1 1 calc R U . . .
C14 C 0.4141(3) 0.4265(5) 0.9113(2) 0.0131(6) Uani 1 1 d . . . . .
H14 H 0.3995 0.5430 0.9594 0.016 Uiso 1 1 calc R U . . .
N1 N 0.1692(2) 0.5084(4) 0.55866(18) 0.0102(5) Uani 1 1 d . . . . .
H1 H 0.1147 0.6369 0.5284 0.012 Uiso 1 1 calc R U . . .
N2 N 0.0703(2) 0.1439(4) 0.79557(19) 0.0116(5) Uani 1 1 d . . . . .
H2C H -0.0081 0.1172 0.7872 0.014 Uiso 1 1 calc R U . . .
H2D H 0.1076 0.0061 0.7969 0.014 Uiso 1 1 calc R U . . .
O1 O 0.08718(17) 0.0707(4) 0.56985(15) 0.0119(4) Uani 1 1 d . . . . .
O2 O 0.10624(18) -0.0349(4) 0.40195(16) 0.0139(4) Uani 1 1 d . . . . .
O3 O 0.11741(18) 0.5959(4) 0.77616(15) 0.0129(4) Uani 1 1 d . . . . .
O4 O 0.12314(19) 0.6760(4) 0.95266(16) 0.0159(4) Uani 1 1 d . . . . .
O5 O 0.62339(18) 0.2980(4) 0.73015(17) 0.0195(5) Uani 1 1 d . . . . .
H5 H 0.6632 0.4162 0.7504 0.029 Uiso 1 1 calc R U . . .
O6 O 0.8309(2) 0.0322(4) 0.83254(19) 0.0176(5) Uani 1 1 d . . . . .
H6A H 0.766(4) 0.107(8) 0.798(3) 0.026 Uiso 1 1 d . U . . .
H6B H 0.845(3) 0.072(8) 0.895(4) 0.026 Uiso 1 1 d . U . . .
O7 O 0.8082(2) 0.5669(4) 0.7865(2) 0.0201(5) Uani 1 1 d . . . . .
H7A H 0.819(4) 0.706(9) 0.803(4) 0.030 Uiso 1 1 d . U . . .
H7B H 0.834(4) 0.554(8) 0.733(4) 0.030 Uiso 1 1 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
Cu1 O3 1.949(2) . ?
Cu1 O1 1.954(2) . ?
Cu1 N2 1.976(2) . ?
Cu1 N1 2.001(2) . ?
C1 N1 1.505(4) . ?
C1 C2 1.524(4) . ?
C1 H1A 0.9700 . ?
C1 H1B 0.9700 . ?
C2 C3 1.525(5) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C4 1.544(3) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C4 N1 1.497(4) . ?
C4 C5 1.518(4) . ?
C4 H4 0.9800 . ?
C5 O2 1.250(4) . ?
C5 O1 1.281(3) . ?
C6 N2 1.484(4) . ?
C6 C7 1.523(4) . ?
C6 C8 1.538(4) . ?
C6 H6 0.9800 . ?
C7 O4 1.240(4) . ?
C7 O3 1.288(3) . ?
C8 C9 1.513(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C14 1.394(4) . ?
C9 C10 1.397(4) . ?
C10 C11 1.392(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.388(4) . ?
C11 H11 0.9300 . ?
C12 O5 1.376(3) . ?
C12 C13 1.386(4) . ?
C13 C14 1.393(4) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
N1 H1 0.9800 . ?
N2 H2C 0.8900 . ?
N2 H2D 0.8900 . ?
O5 H5 0.8200 . ?
O6 H6A 0.88(5) . ?
O6 H6B 0.79(4) . ?
O7 H7A 0.82(5) . ?
O7 H7B 0.78(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 Cu1 O1 178.33(9) . . ?
O3 Cu1 N2 84.89(9) . . ?
O1 Cu1 N2 94.16(9) . . ?
O3 Cu1 N1 95.53(9) . . ?
O1 Cu1 N1 85.09(9) . . ?
N2 Cu1 N1 167.17(10) . . ?
N1 C1 C2 105.4(2) . . ?
N1 C1 H1A 110.7 . . ?
C2 C1 H1A 110.7 . . ?
N1 C1 H1B 110.7 . . ?
C2 C1 H1B 110.7 . . ?
H1A C1 H1B 108.8 . . ?
C1 C2 C3 102.5(2) . . ?
C1 C2 H2A 111.3 . . ?
C3 C2 H2A 111.3 . . ?
C1 C2 H2B 111.3 . . ?
C3 C2 H2B 111.3 . . ?
H2A C2 H2B 109.2 . . ?
C2 C3 C4 103.2(3) . . ?
C2 C3 H3A 111.1 . . ?
C4 C3 H3A 111.1 . . ?
C2 C3 H3B 111.1 . . ?
C4 C3 H3B 111.1 . . ?
H3A C3 H3B 109.1 . . ?
N1 C4 C5 111.0(2) . . ?
N1 C4 C3 105.0(2) . . ?
C5 C4 C3 112.2(3) . . ?
N1 C4 H4 109.5 . . ?
C5 C4 H4 109.5 . . ?
C3 C4 H4 109.5 . . ?
O2 C5 O1 122.8(3) . . ?
O2 C5 C4 119.5(2) . . ?
O1 C5 C4 117.7(2) . . ?
N2 C6 C7 108.8(2) . . ?
N2 C6 C8 112.5(2) . . ?
C7 C6 C8 109.6(2) . . ?
N2 C6 H6 108.6 . . ?
C7 C6 H6 108.6 . . ?
C8 C6 H6 108.6 . . ?
O4 C7 O3 123.2(3) . . ?
O4 C7 C6 119.2(3) . . ?
O3 C7 C6 117.5(3) . . ?
C9 C8 C6 116.2(2) . . ?
C9 C8 H8A 108.2 . . ?
C6 C8 H8A 108.2 . . ?
C9 C8 H8B 108.2 . . ?
C6 C8 H8B 108.2 . . ?
H8A C8 H8B 107.4 . . ?
C14 C9 C10 117.7(3) . . ?
C14 C9 C8 121.2(3) . . ?
C10 C9 C8 121.0(3) . . ?
C11 C10 C9 121.5(3) . . ?
C11 C10 H10 119.3 . . ?
C9 C10 H10 119.3 . . ?
C12 C11 C10 119.6(3) . . ?
C12 C11 H11 120.2 . . ?
C10 C11 H11 120.2 . . ?
O5 C12 C13 122.6(3) . . ?
O5 C12 C11 117.4(3) . . ?
C13 C12 C11 120.1(3) . . ?
C12 C13 C14 119.7(3) . . ?
C12 C13 H13 120.1 . . ?
C14 C13 H13 120.1 . . ?
C13 C14 C9 121.4(3) . . ?
C13 C14 H14 119.3 . . ?
C9 C14 H14 119.3 . . ?
C4 N1 C1 108.1(2) . . ?
C4 N1 Cu1 109.59(18) . . ?
C1 N1 Cu1 112.40(16) . . ?
C4 N1 H1 108.9 . . ?
C1 N1 H1 108.9 . . ?
Cu1 N1 H1 108.9 . . ?
C6 N2 Cu1 108.92(17) . . ?
C6 N2 H2C 109.9 . . ?
Cu1 N2 H2C 109.9 . . ?
C6 N2 H2D 109.9 . . ?
Cu1 N2 H2D 109.9 . . ?
H2C N2 H2D 108.3 . . ?
C5 O1 Cu1 115.69(18) . . ?
C7 O3 Cu1 114.30(19) . . ?
C12 O5 H5 109.5 . . ?
H6A O6 H6B 108(4) . . ?
H7A O7 H7B 104(5) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
N1 C1 C2 C3 -34.0(3) . . . . ?
C1 C2 C3 C4 39.7(3) . . . . ?
C2 C3 C4 N1 -30.9(3) . . . . ?
C2 C3 C4 C5 -151.5(2) . . . . ?
N1 C4 C5 O2 170.4(2) . . . . ?
C3 C4 C5 O2 -72.5(3) . . . . ?
N1 C4 C5 O1 -11.2(3) . . . . ?
C3 C4 C5 O1 105.9(3) . . . . ?
N2 C6 C7 O4 162.3(2) . . . . ?
C8 C6 C7 O4 -74.3(3) . . . . ?
N2 C6 C7 O3 -20.9(3) . . . . ?
C8 C6 C7 O3 102.5(3) . . . . ?
N2 C6 C8 C9 61.2(3) . . . . ?
C7 C6 C8 C9 -60.0(3) . . . . ?
C6 C8 C9 C14 95.2(3) . . . . ?
C6 C8 C9 C10 -88.3(3) . . . . ?
C14 C9 C10 C11 0.1(4) . . . . ?
C8 C9 C10 C11 -176.5(3) . . . . ?
C9 C10 C11 C12 -0.3(4) . . . . ?
C10 C11 C12 O5 -179.8(2) . . . . ?
C10 C11 C12 C13 0.1(4) . . . . ?
O5 C12 C13 C14 -179.9(3) . . . . ?
C11 C12 C13 C14 0.3(4) . . . . ?
C12 C13 C14 C9 -0.4(4) . . . . ?
C10 C9 C14 C13 0.3(4) . . . . ?
C8 C9 C14 C13 176.8(3) . . . . ?
C5 C4 N1 C1 131.2(2) . . . . ?
C3 C4 N1 C1 9.8(3) . . . . ?
C5 C4 N1 Cu1 8.4(2) . . . . ?
C3 C4 N1 Cu1 -113.0(2) . . . . ?
C2 C1 N1 C4 15.1(3) . . . . ?
C2 C1 N1 Cu1 136.2(2) . . . . ?
C7 C6 N2 Cu1 24.9(3) . . . . ?
C8 C6 N2 Cu1 -96.7(2) . . . . ?
O2 C5 O1 Cu1 -173.4(2) . . . . ?
C4 C5 O1 Cu1 8.3(3) . . . . ?
O4 C7 O3 Cu1 -177.7(2) . . . . ?
C6 C7 O3 Cu1 5.7(3) . . . . ?

_refine_diff_density_max         0.207
_refine_diff_density_min         -0.286
_refine_diff_density_rms         0.049

_shelxl_version_number           2014-3

