# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2018

####################################################################### 
# 
# 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_cu
_database_code_depnum_ccdc_archive 'CCDC 1812937'
_audit_update_record             
;
2017-12-21 deposited with the CCDC.
2018-01-02 downloaded from the CCDC.
;
_audit_creation_date             2017-12-21
_audit_creation_method           
;
Olex2 1.2-alpha
(compiled 2017.12.08 svn.r3473 for OlexSys, GUI svn.r5433)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C10 H8 Cu0.5 N O2, 0.5(H2 O)'
_chemical_formula_sum            'C10 H9 Cu0.50 N O2.50'
_chemical_formula_weight         214.95
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C1 H1 O1 N1 Cu1'
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           15
_space_group_name_H-M_alt        'C 1 2/c 1'
_space_group_name_Hall           '-C 2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'

_cell_length_a                   5.6113(3)
_cell_length_b                   19.4865(8)
_cell_length_c                   17.0719(7)
_cell_angle_alpha                90
_cell_angle_beta                 98.664(4)
_cell_angle_gamma                90
_cell_volume                     1845.42(15)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    7370
_cell_measurement_temperature    99.9(3)
_cell_measurement_theta_max      28.8700
_cell_measurement_theta_min      4.1450
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.219
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.88064
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.38.43f (Rigaku Oxford Diffraction, 2015)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear light blue'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   light
_exptl_crystal_colour_primary    blue
_exptl_crystal_density_diffrn    1.547
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             884
_exptl_crystal_size_max          0.22
_exptl_crystal_size_mid          0.21
_exptl_crystal_size_min          0.18
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0201
_diffrn_reflns_av_unetI/netI     0.0218
_diffrn_reflns_Laue_measured_fraction_full 0.984
_diffrn_reflns_Laue_measured_fraction_max 0.983
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            5331
_diffrn_reflns_point_group_measured_fraction_full 0.984
_diffrn_reflns_point_group_measured_fraction_max 0.983
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         26.366
_diffrn_reflns_theta_min         3.819
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      99.9(3)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 8.0359
_diffrn_detector_type            EosS2
_diffrn_measured_fraction_theta_full 0.984
_diffrn_measured_fraction_theta_max 0.983
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):
  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -53.00  31.00   1.00   30.00    --   14.24 -57.00   0.00   84
  2  ω    -55.00  84.00   1.00   30.00    --   14.24   0.00-120.00  139
  3  ω    -44.00   7.00   1.00   30.00    --  -16.97  77.00 120.00   51
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'SuperNova, Single source at offset, EosS2'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0118348000
_diffrn_orient_matrix_UB_12      0.0288297000
_diffrn_orient_matrix_UB_13      0.0245042000
_diffrn_orient_matrix_UB_21      -0.1183432000
_diffrn_orient_matrix_UB_22      -0.0106307000
_diffrn_orient_matrix_UB_23      0.0041956000
_diffrn_orient_matrix_UB_31      0.0470297000
_diffrn_orient_matrix_UB_32      -0.0195168000
_diffrn_orient_matrix_UB_33      0.0338880000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'SuperNova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1776
_reflns_number_total             1856
_reflns_odcompleteness_completeness 97.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_collection       'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_computing_data_reduction        'CrysAlisPro 1.171.38.43f (Rigaku OD, 2015)'
_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    ?
_refine_diff_density_max         0.386
_refine_diff_density_min         -0.355
_refine_diff_density_rms         0.060
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.107
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     132
_refine_ls_number_reflns         1856
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0272
_refine_ls_R_factor_gt           0.0258
_refine_ls_restrained_S_all      1.107
_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)+(0.0225P)²+3.5939P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0632
_refine_ls_wR_factor_ref         0.0638
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H,H) groups
2. Others
 Fixed Sof: H8A(0.5) H8B(0.5)
3.a Free rotating group:
 O8(H8A,H8B)
3.b Aromatic/amide H refined with riding coordinates:
 C3(H3), C10(H10), C4(H4), C13(H13), C12(H12)
3.c Idealised Me refined as rotating group:
 C15(H15A,H15B,H15C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     ?
_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 0.5000 0.42262(2) 0.7500 0.00931(10) Uani 1 2 d S T P . .
O7 O 0.3180(2) 0.35336(6) 0.68269(7) 0.0121(3) Uani 1 1 d . . . . .
O6 O 0.6216(2) 0.37987(6) 0.61880(7) 0.0160(3) Uani 1 1 d . . . . .
O8 O 0.0000 0.26813(9) 0.7500 0.0174(4) Uani 1 2 d S T P . .
H8A H 0.0763 0.2970 0.7259 0.026 Uiso 0.5 1 d G . . . .
H8B H -0.1317 0.2858 0.7589 0.026 Uiso 0.5 1 d G . . . .
N9 N 0.7027(3) 0.50014(7) 0.79827(8) 0.0109(3) Uani 1 1 d . . . . .
C5 C 0.4362(3) 0.34685(8) 0.62397(10) 0.0109(3) Uani 1 1 d . . . . .
C14 C 0.6129(3) 0.56332(9) 0.77875(10) 0.0118(4) Uani 1 1 d . . . . .
C2 C 0.3368(3) 0.29655(8) 0.55998(10) 0.0103(3) Uani 1 1 d . . . . .
C3 C 0.1167(3) 0.26334(9) 0.56095(10) 0.0124(4) Uani 1 1 d . . . . .
H3 H 0.0270 0.2723 0.6014 0.015 Uiso 1 1 calc R . . . .
C10 C 0.9089(3) 0.49398(9) 0.84921(10) 0.0126(4) Uani 1 1 d . . . . .
H10 H 0.9709 0.4503 0.8611 0.015 Uiso 1 1 calc R . . . .
C4 C 0.0316(3) 0.21686(9) 0.50125(10) 0.0124(4) Uani 1 1 d . . . . .
H4 H -0.1145 0.1946 0.5023 0.015 Uiso 1 1 calc R . . . .
C13 C 0.7267(3) 0.62203(9) 0.81158(11) 0.0165(4) Uani 1 1 d . . . . .
H13 H 0.6631 0.6652 0.7979 0.020 Uiso 1 1 calc R . . . .
C11 C 1.0332(3) 0.55025(9) 0.88480(11) 0.0146(4) Uani 1 1 d . . . . .
C12 C 0.9377(4) 0.61509(9) 0.86538(11) 0.0176(4) Uani 1 1 d . . . . .
H12 H 1.0154 0.6539 0.8884 0.021 Uiso 1 1 calc R . . . .
C15 C 1.2608(4) 0.53971(10) 0.94290(11) 0.0198(4) Uani 1 1 d . . . . .
H15A H 1.2273 0.5466 0.9958 0.030 Uiso 1 1 calc GR . . . .
H15B H 1.3809 0.5720 0.9320 0.030 Uiso 1 1 calc GR . . . .
H15C H 1.3191 0.4938 0.9378 0.030 Uiso 1 1 calc GR . . . .


_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 O7 1.9573(12) 2_656 ?
Cu1 O7 1.9574(12) . ?
Cu1 N9 1.9930(14) 2_656 ?
Cu1 N9 1.9931(14) . ?
O7 C5 1.289(2) . ?
O6 C5 1.238(2) . ?
O8 H8A 0.8502 . ?
O8 H8B 0.8502 . ?
N9 C14 1.353(2) . ?
N9 C10 1.344(2) . ?
C5 C2 1.510(2) . ?
C14 C14 1.482(3) 2_656 ?
C14 C13 1.387(2) . ?
C2 C3 1.396(3) . ?
C2 C4 1.393(3) 7_556 ?
C3 H3 0.9300 . ?
C3 C4 1.393(2) . ?
C10 H10 0.9300 . ?
C10 C11 1.389(3) . ?
C4 C2 1.393(3) 7_556 ?
C4 H4 0.9300 . ?
C13 H13 0.9300 . ?
C13 C12 1.392(3) . ?
C11 C12 1.393(3) . ?
C11 C15 1.509(3) . ?
C12 H12 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?

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
O7 Cu1 O7 92.82(7) 2_656 . ?
O7 Cu1 N9 168.55(5) . . ?
O7 Cu1 N9 168.56(5) 2_656 2_656 ?
O7 Cu1 N9 93.73(5) . 2_656 ?
O7 Cu1 N9 93.73(5) 2_656 . ?
N9 Cu1 N9 81.45(8) 2_656 . ?
C5 O7 Cu1 103.92(11) . . ?
H8A O8 H8B 109.5 . . ?
C14 N9 Cu1 114.81(12) . . ?
C10 N9 Cu1 125.59(12) . . ?
C10 N9 C14 119.55(15) . . ?
O7 C5 C2 116.70(15) . . ?
O6 C5 O7 122.73(16) . . ?
O6 C5 C2 120.57(16) . . ?
N9 C14 C14 114.39(10) . 2_656 ?
N9 C14 C13 121.31(16) . . ?
C13 C14 C14 124.30(10) . 2_656 ?
C3 C2 C5 121.54(16) . . ?
C4 C2 C5 118.99(16) 7_556 . ?
C4 C2 C3 119.47(16) 7_556 . ?
C2 C3 H3 120.0 . . ?
C4 C3 C2 119.94(17) . . ?
C4 C3 H3 120.0 . . ?
N9 C10 H10 118.7 . . ?
N9 C10 C11 122.60(16) . . ?
C11 C10 H10 118.7 . . ?
C2 C4 C3 120.59(17) 7_556 . ?
C2 C4 H4 119.7 7_556 . ?
C3 C4 H4 119.7 . . ?
C14 C13 H13 120.6 . . ?
C14 C13 C12 118.73(17) . . ?
C12 C13 H13 120.6 . . ?
C10 C11 C12 117.55(17) . . ?
C10 C11 C15 119.96(16) . . ?
C12 C11 C15 122.49(17) . . ?
C13 C12 C11 120.25(17) . . ?
C13 C12 H12 119.9 . . ?
C11 C12 H12 119.9 . . ?
C11 C15 H15A 109.5 . . ?
C11 C15 H15B 109.5 . . ?
C11 C15 H15C 109.5 . . ?
H15A C15 H15B 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?

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
Cu1 O7 C5 O6 0.37(19) . . . . ?
Cu1 O7 C5 C2 -179.28(11) . . . . ?
Cu1 N9 C14 C14 -3.4(2) . . . 2_656 ?
Cu1 N9 C14 C13 176.06(14) . . . . ?
Cu1 N9 C10 C11 -175.56(13) . . . . ?
O7 C5 C2 C3 5.5(2) . . . . ?
O7 C5 C2 C4 -174.50(15) . . . 7_556 ?
O6 C5 C2 C3 -174.18(16) . . . . ?
O6 C5 C2 C4 5.8(2) . . . 7_556 ?
N9 C14 C13 C12 0.2(3) . . . . ?
N9 C10 C11 C12 -0.6(3) . . . . ?
N9 C10 C11 C15 178.62(17) . . . . ?
C5 C2 C3 C4 -179.50(15) . . . . ?
C14 N9 C10 C11 1.6(3) . . . . ?
C14 C14 C13 C12 179.6(2) 2_656 . . . ?
C14 C13 C12 C11 0.8(3) . . . . ?
C2 C3 C4 C2 -0.5(3) . . . 7_556 ?
C10 N9 C14 C14 179.13(18) . . . 2_656 ?
C10 N9 C14 C13 -1.4(3) . . . . ?
C10 C11 C12 C13 -0.6(3) . . . . ?
C4 C2 C3 C4 0.5(3) 7_556 . . . ?
C15 C11 C12 C13 -179.80(18) . . . . ?

_olex2_date_sample_data_collection 2017-03-17
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.252
_oxdiff_exptl_absorpt_empirical_full_min 0.808
