# Electronic Supplementary Material (ESI) for Journal of Materials Chemistry C.
# This journal is © The Royal Society of Chemistry 2015

####################################################################### 
# 
# 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_a
_database_code_depnum_ccdc_archive 'CCDC 909604'
_audit_update_record             
;
2012-11-07 deposited with the CCDC.
2015-09-24 downloaded from the CCDC.
;
#TrackingRef 'web_deposit_cif_file_0_NorbaniAbdullah_1352275165.drs.cif'


_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C19 H30 Cu N O4'
_chemical_formula_sum            'C19 H30 Cu N O4'
_chemical_formula_weight         399.98

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'

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   C2/c
_symmetry_space_group_name_Hall  '-C 2yc'
loop_
_symmetry_equiv_pos_as_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                   16.873(3)
_cell_length_b                   25.268(5)
_cell_length_c                   10.680(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 119.457(2)
_cell_angle_gamma                90.00
_cell_volume                     3964.6(14)
_cell_formula_units_Z            8
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    1644
_cell_measurement_theta_min      2.77
_cell_measurement_theta_max      24.53

_exptl_crystal_description       block
_exptl_crystal_colour            green
_exptl_crystal_size_max          0.52
_exptl_crystal_size_mid          0.44
_exptl_crystal_size_min          0.39
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.340
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1696
_exptl_absorpt_coefficient_mu    1.123
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5927
_exptl_absorpt_correction_T_max  0.6684
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            13086
_diffrn_reflns_av_R_equivalents  0.0637
_diffrn_reflns_av_sigmaI/netI    0.0774
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_k_max       32
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         1.60
_diffrn_reflns_theta_max         27.50
_reflns_number_total             4527
_reflns_number_gt                3121
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker APEX2'
_computing_cell_refinement       'Bruker SAINT'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
;
Refinement of F² against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F², conventional R-factors R are based
on F, with F set to zero for negative F². The threshold expression of
F² > 2sigma(F²) is used only for calculating R-factors(gt) 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     
'calc w=1/[σ²(Fo²)+(0.0527P)²] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         4527
_refine_ls_number_parameters     228
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0778
_refine_ls_R_factor_gt           0.0450
_refine_ls_wR_factor_ref         0.1207
_refine_ls_wR_factor_gt          0.1049
_refine_ls_goodness_of_fit_ref   1.000
_refine_ls_restrained_S_all      1.000
_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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cu1 Cu 0.20670(2) 0.245297(13) 0.86000(4) 0.01302(12) Uani 1 1 d . . .
O1 O 0.28921(14) 0.30091(8) 0.8613(2) 0.0193(5) Uani 1 1 d . . .
O2 O 0.12894(14) 0.30247(8) 0.8663(2) 0.0183(5) Uani 1 1 d . . .
O3 O 0.29882(14) 0.19086(8) 0.8933(2) 0.0179(5) Uani 1 1 d . . .
O4 O 0.13797(14) 0.19080(8) 0.8989(2) 0.0191(5) Uani 1 1 d . . .
N1 N 0.12925(17) 0.23785(9) 0.6304(3) 0.0145(5) Uani 1 1 d . . .
C1 C 0.3447(2) 0.32379(11) 0.9775(3) 0.0170(7) Uani 1 1 d . . .
C2 C 0.3925(2) 0.37296(12) 0.9690(3) 0.0215(7) Uani 1 1 d . . .
H2A H 0.4590 0.3672 1.0265 0.026 Uiso 1 1 calc R . .
H2B H 0.3769 0.4026 1.0138 0.026 Uiso 1 1 calc R . .
C3 C 0.3695(3) 0.38938(13) 0.8177(4) 0.0321(9) Uani 1 1 d . . .
H3A H 0.3025 0.3887 0.7556 0.038 Uiso 1 1 calc R . .
H3B H 0.3953 0.3628 0.7796 0.038 Uiso 1 1 calc R . .
C4 C 0.4042(3) 0.44405(12) 0.8066(4) 0.0274(8) Uani 1 1 d . . .
H4A H 0.4708 0.4453 0.8726 0.033 Uiso 1 1 calc R . .
H4B H 0.3936 0.4488 0.7076 0.033 Uiso 1 1 calc R . .
C5 C 0.3604(2) 0.48996(12) 0.8420(4) 0.0245(8) Uani 1 1 d . . .
H5A H 0.3817 0.4899 0.9465 0.029 Uiso 1 1 calc R . .
H5B H 0.2935 0.4851 0.7907 0.029 Uiso 1 1 calc R . .
C6 C 0.3829(2) 0.54323(13) 0.7998(4) 0.0271(8) Uani 1 1 d . . .
H6A H 0.4498 0.5470 0.8470 0.033 Uiso 1 1 calc R . .
H6B H 0.3589 0.5436 0.6946 0.033 Uiso 1 1 calc R . .
C7 C 0.3440(3) 0.59044(14) 0.8405(4) 0.0363(9) Uani 1 1 d . . .
H7A H 0.2777 0.5869 0.7950 0.054 Uiso 1 1 calc R . .
H7B H 0.3591 0.6231 0.8075 0.054 Uiso 1 1 calc R . .
H7C H 0.3702 0.5916 0.9452 0.054 Uiso 1 1 calc R . .
C8 C 0.1429(2) 0.32432(11) 0.9818(3) 0.0150(6) Uani 1 1 d . . .
C9 C 0.0902(2) 0.37372(11) 0.9711(3) 0.0182(7) Uani 1 1 d . . .
H9A H 0.0891 0.3791 1.0621 0.022 Uiso 1 1 calc R . .
H9B H 0.0266 0.3699 0.8924 0.022 Uiso 1 1 calc R . .
C10 C 0.1344(2) 0.42176(12) 0.9417(3) 0.0210(7) Uani 1 1 d . . .
H10A H 0.2007 0.4211 1.0092 0.025 Uiso 1 1 calc R . .
H10B H 0.1250 0.4192 0.8428 0.025 Uiso 1 1 calc R . .
C11 C 0.0956(2) 0.47403(12) 0.9580(4) 0.0234(7) Uani 1 1 d . . .
H11A H 0.1050 0.4763 1.0569 0.028 Uiso 1 1 calc R . .
H11B H 0.0292 0.4743 0.8908 0.028 Uiso 1 1 calc R . .
C12 C 0.1379(2) 0.52298(12) 0.9292(4) 0.0245(8) Uani 1 1 d . . .
H12A H 0.2049 0.5214 0.9907 0.029 Uiso 1 1 calc R . .
H12B H 0.1238 0.5226 0.8276 0.029 Uiso 1 1 calc R . .
C13 C 0.1031(3) 0.57431(12) 0.9586(4) 0.0295(8) Uani 1 1 d . . .
H13A H 0.1183 0.5749 1.0607 0.035 Uiso 1 1 calc R . .
H13B H 0.0360 0.5753 0.8987 0.035 Uiso 1 1 calc R . .
C14 C 0.1430(3) 0.62375(13) 0.9276(4) 0.0370(9) Uani 1 1 d . . .
H14A H 0.2096 0.6228 0.9854 0.055 Uiso 1 1 calc R . .
H14B H 0.1200 0.6554 0.9523 0.055 Uiso 1 1 calc R . .
H14C H 0.1250 0.6247 0.8253 0.055 Uiso 1 1 calc R . .
C15 C 0.0410(2) 0.25034(11) 0.5615(3) 0.0166(6) Uani 1 1 d . . .
H15 H 0.0132 0.2598 0.6171 0.020 Uiso 1 1 calc R . .
C16 C -0.0124(2) 0.25029(11) 0.4125(3) 0.0164(6) Uani 1 1 d . . .
H16 H -0.0751 0.2594 0.3680 0.020 Uiso 1 1 calc R . .
C17 C 0.0271(2) 0.23681(11) 0.3298(3) 0.0152(6) Uani 1 1 d . . .
C18 C 0.1196(2) 0.22337(11) 0.4010(3) 0.0148(6) Uani 1 1 d . . .
H18 H 0.1492 0.2140 0.3481 0.018 Uiso 1 1 calc R . .
C19 C 0.1669(2) 0.22408(11) 0.5495(3) 0.0152(6) Uani 1 1 d . . .
H19 H 0.2293 0.2143 0.5970 0.018 Uiso 1 1 calc R . .


_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 O4 1.971(2) . Y
Cu1 O3 1.973(2) . Y
Cu1 O1 1.974(2) . Y
Cu1 O2 1.975(2) . Y
Cu1 N1 2.146(2) . Y
Cu1 Cu1 2.6145(8) 7_557 Y
O1 C1 1.269(4) . ?
O2 C8 1.263(3) . ?
O3 C8 1.266(3) 7_557 ?
O4 C1 1.259(4) 7_557 ?
N1 C15 1.334(4) . ?
N1 C19 1.346(4) . ?
C1 O4 1.259(4) 7_557 ?
C1 C2 1.507(4) . ?
C2 C3 1.522(4) . ?
C2 H2A 0.9900 . ?
C2 H2B 0.9900 . ?
C3 C4 1.528(4) . ?
C3 H3A 0.9900 . ?
C3 H3B 0.9900 . ?
C4 C5 1.520(5) . ?
C4 H4A 0.9900 . ?
C4 H4B 0.9900 . ?
C5 C6 1.525(4) . ?
C5 H5A 0.9900 . ?
C5 H5B 0.9900 . ?
C6 C7 1.524(5) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 O3 1.266(3) 7_557 ?
C8 C9 1.504(4) . ?
C9 C10 1.535(4) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 C11 1.521(4) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C12 1.532(4) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C12 C13 1.519(4) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C14 1.530(5) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C14 H14A 0.9800 . ?
C14 H14B 0.9800 . ?
C14 H14C 0.9800 . ?
C15 C16 1.391(4) . ?
C15 H15 0.9500 . ?
C16 C17 1.385(4) . ?
C16 H16 0.9500 . ?
C17 C18 1.400(4) . ?
C17 C17 1.486(6) 2 ?
C18 C19 1.381(4) . ?
C18 H18 0.9500 . ?
C19 H19 0.9500 . ?

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
O4 Cu1 O3 88.16(9) . . Y
O4 Cu1 O1 169.10(8) . . Y
O3 Cu1 O1 90.26(9) . . Y
O4 Cu1 O2 91.97(9) . . Y
O3 Cu1 O2 169.06(8) . . Y
O1 Cu1 O2 87.55(9) . . Y
O4 Cu1 N1 95.08(9) . . Y
O3 Cu1 N1 97.35(9) . . Y
O1 Cu1 N1 95.81(9) . . Y
O2 Cu1 N1 93.54(9) . . Y
O4 Cu1 Cu1 83.03(6) . 7_557 Y
O3 Cu1 Cu1 84.81(6) . 7_557 Y
O1 Cu1 Cu1 86.10(6) . 7_557 Y
O2 Cu1 Cu1 84.35(6) . 7_557 Y
N1 Cu1 Cu1 177.10(7) . 7_557 Y
C1 O1 Cu1 120.67(19) . . ?
C8 O2 Cu1 123.01(19) . . ?
C8 O3 Cu1 122.38(19) 7_557 . ?
C1 O4 Cu1 124.63(19) 7_557 . ?
C15 N1 C19 117.3(3) . . ?
C15 N1 Cu1 119.79(19) . . ?
C19 N1 Cu1 122.8(2) . . ?
O4 C1 O1 124.9(3) 7_557 . ?
O4 C1 C2 116.7(3) 7_557 . ?
O1 C1 C2 118.4(3) . . ?
C1 C2 C3 115.1(3) . . ?
C1 C2 H2A 108.5 . . ?
C3 C2 H2A 108.5 . . ?
C1 C2 H2B 108.5 . . ?
C3 C2 H2B 108.5 . . ?
H2A C2 H2B 107.5 . . ?
C2 C3 C4 114.9(3) . . ?
C2 C3 H3A 108.5 . . ?
C4 C3 H3A 108.5 . . ?
C2 C3 H3B 108.5 . . ?
C4 C3 H3B 108.5 . . ?
H3A C3 H3B 107.5 . . ?
C5 C4 C3 114.8(3) . . ?
C5 C4 H4A 108.6 . . ?
C3 C4 H4A 108.6 . . ?
C5 C4 H4B 108.6 . . ?
C3 C4 H4B 108.6 . . ?
H4A C4 H4B 107.5 . . ?
C4 C5 C6 112.2(3) . . ?
C4 C5 H5A 109.2 . . ?
C6 C5 H5A 109.2 . . ?
C4 C5 H5B 109.2 . . ?
C6 C5 H5B 109.2 . . ?
H5A C5 H5B 107.9 . . ?
C7 C6 C5 113.7(3) . . ?
C7 C6 H6A 108.8 . . ?
C5 C6 H6A 108.8 . . ?
C7 C6 H6B 108.8 . . ?
C5 C6 H6B 108.8 . . ?
H6A C6 H6B 107.7 . . ?
C6 C7 H7A 109.5 . . ?
C6 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C6 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
O2 C8 O3 124.9(3) . 7_557 ?
O2 C8 C9 118.0(3) . . ?
O3 C8 C9 117.0(3) 7_557 . ?
C8 C9 C10 110.1(3) . . ?
C8 C9 H9A 109.6 . . ?
C10 C9 H9A 109.6 . . ?
C8 C9 H9B 109.6 . . ?
C10 C9 H9B 109.6 . . ?
H9A C9 H9B 108.2 . . ?
C11 C10 C9 112.6(3) . . ?
C11 C10 H10A 109.1 . . ?
C9 C10 H10A 109.1 . . ?
C11 C10 H10B 109.1 . . ?
C9 C10 H10B 109.1 . . ?
H10A C10 H10B 107.8 . . ?
C10 C11 C12 114.2(3) . . ?
C10 C11 H11A 108.7 . . ?
C12 C11 H11A 108.7 . . ?
C10 C11 H11B 108.7 . . ?
C12 C11 H11B 108.7 . . ?
H11A C11 H11B 107.6 . . ?
C13 C12 C11 112.5(3) . . ?
C13 C12 H12A 109.1 . . ?
C11 C12 H12A 109.1 . . ?
C13 C12 H12B 109.1 . . ?
C11 C12 H12B 109.1 . . ?
H12A C12 H12B 107.8 . . ?
C12 C13 C14 113.4(3) . . ?
C12 C13 H13A 108.9 . . ?
C14 C13 H13A 108.9 . . ?
C12 C13 H13B 108.9 . . ?
C14 C13 H13B 108.9 . . ?
H13A C13 H13B 107.7 . . ?
C13 C14 H14A 109.5 . . ?
C13 C14 H14B 109.5 . . ?
H14A C14 H14B 109.5 . . ?
C13 C14 H14C 109.5 . . ?
H14A C14 H14C 109.5 . . ?
H14B C14 H14C 109.5 . . ?
N1 C15 C16 123.4(3) . . ?
N1 C15 H15 118.3 . . ?
C16 C15 H15 118.3 . . ?
C17 C16 C15 119.1(3) . . ?
C17 C16 H16 120.5 . . ?
C15 C16 H16 120.5 . . ?
C16 C17 C18 118.1(3) . . ?
C16 C17 C17 120.9(3) . 2 ?
C18 C17 C17 121.0(3) . 2 ?
C19 C18 C17 118.7(3) . . ?
C19 C18 H18 120.6 . . ?
C17 C18 H18 120.6 . . ?
N1 C19 C18 123.5(3) . . ?
N1 C19 H19 118.2 . . ?
C18 C19 H19 118.2 . . ?

_diffrn_measured_fraction_theta_max 0.995
_diffrn_reflns_theta_full        27.50
_diffrn_measured_fraction_theta_full 0.995
_refine_diff_density_max         0.529
_refine_diff_density_min         -0.838
_refine_diff_density_rms         0.095


