# Electronic Supplementary Material (ESI) for Lab on a Chip.
# This journal is © The Royal Society of Chemistry 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_0608l1_0m
_database_code_depnum_ccdc_archive 'CCDC 2202418'
loop_
_audit_author_name
_audit_author_address
'Wei Liu'
;North University of China
China
;
_audit_update_record             
;
2022-08-19 deposited with the CCDC.	2023-09-15 downloaded from the CCDC.
;
_audit_creation_date             2022-06-08
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C4 H4 Cu N8 O8, 3(H2 O)'
_chemical_formula_sum            'C4 H10 Cu N8 O11'
_chemical_formula_weight         409.74
_chemical_melting_point          ?
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'
Cu Cu 0.3201 1.2651 '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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/c 1'
_space_group_name_Hall           '-P 2ybc'
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                   11.4854(8)
_cell_length_b                   9.3738(6)
_cell_length_c                   12.6139(10)
_cell_angle_alpha                90
_cell_angle_beta                 99.830(3)
_cell_angle_gamma                90
_cell_volume                     1338.10(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    2971
_cell_measurement_temperature    170
_cell_measurement_theta_max      26.157
_cell_measurement_theta_min      2.721
_shelx_estimated_absorpt_T_max   0.919
_shelx_estimated_absorpt_T_min   0.820
_exptl_absorpt_coefficient_mu    1.718
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.6529
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
'SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0961 before and 0.0626 after correction. The Ratio of minimum to maximum transmission is 0.8759. The λ/2 correction factor is Not present.'
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    2.034
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             828
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0626
_diffrn_reflns_av_unetI/netI     0.0535
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.988
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            12336
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.988
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.412
_diffrn_reflns_theta_min         2.722
_diffrn_ambient_temperature      170.0
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.988
_diffrn_measurement_device_type  'Bruker D8 VENTURE'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_diffrn_standards_number         0
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                2109
_reflns_number_total             2717
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'SAINT V8.40A (?, 2016)'
_computing_data_collection       ?
_computing_data_reduction        'SAINT V8.40A (?, 2016)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.422
_refine_diff_density_min         -0.446
_refine_diff_density_rms         0.095
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         2717
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0613
_refine_ls_R_factor_gt           0.0387
_refine_ls_restrained_S_all      1.096
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0145P)²+1.8201P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0677
_refine_ls_wR_factor_ref         0.0774
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.5 times of:
  All O(H) groups, All O(H,H) groups
2. Restrained distances
 O3-H3A = O3-H3B
 0.87 with sigma of 0.02
 O8-H8A = O8-H8B
 0.87 with sigma of 0.02
 O4-H4B = O4-H4A
 0.87 with sigma of 0.02
3.a Free rotating group:
 O6(H6A,H6B), O7(H7A,H7B)
3.b Rotating group:
 O4(H4A)
;
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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 0.26889(3) 0.92483(4) 0.33709(3) 0.01501(12) Uani 1 1 d . . . . .
O9 O 0.20487(19) 0.3352(2) 0.43380(19) 0.0171(5) Uani 1 1 d . . . . .
O5 O 0.34155(18) 0.5195(2) 0.23426(18) 0.0169(5) Uani 1 1 d . . . . .
O3 O 0.1135(2) 0.9420(2) 0.2400(2) 0.0201(5) Uani 1 1 d D . . . .
O4 O 0.4208(2) 0.9054(2) 0.4357(2) 0.0225(6) Uani 1 1 d D . . . .
H4A H 0.466797 0.845058 0.408511 0.034 Uiso 1 1 d DGR . . . .
O11 O 0.1745(2) -0.0822(2) 0.4847(2) 0.0251(6) Uani 1 1 d . . . . .
O6 O 0.5777(2) 0.7187(2) 0.3854(2) 0.0268(6) Uani 1 1 d . . . . .
H6A H 0.569399 0.631361 0.406129 0.040 Uiso 1 1 d G . . . .
H6B H 0.609385 0.718568 0.327489 0.040 Uiso 1 1 d G . . . .
O10 O 0.0897(2) -0.0251(3) 0.61894(19) 0.0243(6) Uani 1 1 d . . . . .
N6 N 0.2810(2) 0.7221(3) 0.2945(2) 0.0142(6) Uani 1 1 d . . . . .
O2 O 0.4540(2) 0.8956(2) 0.0629(2) 0.0284(6) Uani 1 1 d . . . . .
N5 N 0.2442(2) 0.6111(3) 0.3555(2) 0.0158(6) Uani 1 1 d . . . . .
O8 O 0.0406(2) 1.2145(3) 0.2047(3) 0.0326(7) Uani 1 1 d D . . . .
N3 N 0.2601(2) 0.1285(3) 0.3765(2) 0.0157(6) Uani 1 1 d . . . . .
O1 O 0.3684(2) 0.9390(2) 0.1975(2) 0.0354(7) Uani 1 1 d . . . . .
N4 N 0.3005(2) 0.2360(3) 0.3144(2) 0.0170(6) Uani 1 1 d . . . . .
N7 N 0.3945(2) 0.7106(3) 0.1450(2) 0.0177(6) Uani 1 1 d . . . . .
N8 N 0.4044(2) 0.8524(3) 0.1355(2) 0.0200(7) Uani 1 1 d . . . . .
N1 N 0.1381(2) 0.0104(3) 0.5425(2) 0.0200(7) Uani 1 1 d . . . . .
N2 N 0.1488(2) 0.1507(3) 0.5275(2) 0.0196(7) Uani 1 1 d . . . . .
O7 O 0.1006(3) 0.8629(3) 0.0414(2) 0.0470(8) Uani 1 1 d . . . . .
H7A H 0.105177 0.772251 0.027935 0.070 Uiso 1 1 d G . . . .
H7B H 0.114378 0.911881 -0.013717 0.070 Uiso 1 1 d G . . . .
C4 C 0.3388(3) 0.6651(3) 0.2237(3) 0.0149(7) Uani 1 1 d . . . . .
C1 C 0.2041(3) 0.1905(3) 0.4466(3) 0.0163(7) Uani 1 1 d . . . . .
C3 C 0.2816(3) 0.4969(3) 0.3166(3) 0.0152(7) Uani 1 1 d . . . . .
C2 C 0.2659(3) 0.3525(3) 0.3520(3) 0.0163(7) Uani 1 1 d . . . . .
H3A H 0.082(3) 1.025(3) 0.239(3) 0.047(13) Uiso 1 1 d D . . . .
H3B H 0.114(4) 0.915(4) 0.1755(19) 0.046(14) Uiso 1 1 d D . . . .
H8A H 0.070(4) 1.245(5) 0.152(3) 0.08(2) Uiso 1 1 d D . . . .
H8B H -0.012(3) 1.272(4) 0.218(4) 0.074(18) Uiso 1 1 d D . . . .
H4B H 0.419(5) 0.887(5) 0.5016(19) 0.08(2) Uiso 1 1 d 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 O3 1.992(2) . ?
Cu1 O4 1.971(2) . ?
Cu1 O11 2.310(3) 1_565 ?
Cu1 N6 1.986(3) . ?
Cu1 N3 1.980(3) 1_565 ?
Cu1 O1 2.261(3) . ?
O9 C1 1.367(4) . ?
O9 C2 1.353(4) . ?
O5 C4 1.371(4) . ?
O5 C3 1.357(4) . ?
O3 H3A 0.857(19) . ?
O3 H3B 0.853(19) . ?
O4 H4A 0.8817 . ?
O4 H4B 0.85(2) . ?
O11 N1 1.251(4) . ?
O6 H6A 0.8698 . ?
O6 H6B 0.8702 . ?
O10 N1 1.238(4) . ?
N6 N5 1.401(4) . ?
N6 C4 1.314(4) . ?
O2 N8 1.228(4) . ?
N5 C3 1.282(4) . ?
O8 H8A 0.85(2) . ?
O8 H8B 0.848(19) . ?
N3 N4 1.403(4) . ?
N3 C1 1.315(4) . ?
O1 N8 1.245(4) . ?
N4 C2 1.281(4) . ?
N7 N8 1.342(3) . ?
N7 C4 1.340(4) . ?
N1 N2 1.338(4) . ?
N2 C1 1.343(4) . ?
O7 H7A 0.8698 . ?
O7 H7B 0.8702 . ?
C3 C2 1.446(4) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 Cu1 O11 90.19(10) . 1_565 ?
O3 Cu1 O1 92.05(11) . . ?
O4 Cu1 O3 178.63(11) . . ?
O4 Cu1 O11 88.60(10) . 1_565 ?
O4 Cu1 N6 89.25(10) . . ?
O4 Cu1 N3 90.48(10) . 1_565 ?
O4 Cu1 O1 89.18(11) . . ?
N6 Cu1 O3 90.44(10) . . ?
N6 Cu1 O11 104.76(10) . 1_565 ?
N6 Cu1 O1 77.15(10) . . ?
N3 Cu1 O3 89.87(10) 1_565 . ?
N3 Cu1 O11 76.96(10) 1_565 1_565 ?
N3 Cu1 N6 178.26(12) 1_565 . ?
N3 Cu1 O1 101.12(10) 1_565 . ?
O1 Cu1 O11 177.05(9) . 1_565 ?
C2 O9 C1 102.9(2) . . ?
C3 O5 C4 102.9(2) . . ?
Cu1 O3 H3A 114(3) . . ?
Cu1 O3 H3B 114(3) . . ?
H3A O3 H3B 109(4) . . ?
Cu1 O4 H4A 109.8 . . ?
Cu1 O4 H4B 118(4) . . ?
H4A O4 H4B 111.3 . . ?
N1 O11 Cu1 134.4(2) . 1_545 ?
H6A O6 H6B 109.5 . . ?
N5 N6 Cu1 121.4(2) . . ?
C4 N6 Cu1 129.8(2) . . ?
C4 N6 N5 107.8(2) . . ?
C3 N5 N6 104.9(3) . . ?
H8A O8 H8B 109(5) . . ?
N4 N3 Cu1 121.1(2) . 1_545 ?
C1 N3 Cu1 130.3(2) . 1_545 ?
C1 N3 N4 107.7(2) . . ?
N8 O1 Cu1 135.8(2) . . ?
C2 N4 N3 104.6(3) . . ?
C4 N7 N8 116.1(3) . . ?
O2 N8 O1 120.0(3) . . ?
O2 N8 N7 116.7(3) . . ?
O1 N8 N7 123.2(3) . . ?
O11 N1 N2 123.5(3) . . ?
O10 N1 O11 120.5(3) . . ?
O10 N1 N2 116.0(3) . . ?
N1 N2 C1 116.6(3) . . ?
H7A O7 H7B 109.5 . . ?
N6 C4 O5 110.2(3) . . ?
N6 C4 N7 137.3(3) . . ?
N7 C4 O5 112.5(3) . . ?
N3 C1 O9 110.2(3) . . ?
N3 C1 N2 137.5(3) . . ?
N2 C1 O9 112.3(3) . . ?
O5 C3 C2 119.3(3) . . ?
N5 C3 O5 114.2(3) . . ?
N5 C3 C2 126.5(3) . . ?
O9 C2 C3 117.1(3) . . ?
N4 C2 O9 114.5(3) . . ?
N4 C2 C3 128.3(3) . . ?


_olex2_submission_special_instructions 'No special instructions were received'
