# Electronic Supplementary Material (ESI) for RSC Advances.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# 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_icvu_191
_database_code_depnum_ccdc_archive 'CCDC 999890'
_audit_update_record             
;
2015-12-23 deposited with the CCDC.
2016-06-10 downloaded from the CCDC.
;
_audit_creation_date             2014-04-28
_audit_creation_method           
;
Olex2 1.2-ac21
(compiled 2014.04.04 svn.r2922 for OlexSys, GUI svn.r3563)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C22 H26 Cu N2 O4'
_chemical_formula_sum            'C22 H26 Cu N2 O4'
_chemical_formula_weight         445.99
_chemical_melting_point          ?
_chemical_oxdiff_formula         'C10 H10 O2 N2 Cu'
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                   10.7277(3)
_cell_length_b                   19.7595(4)
_cell_length_c                   10.9426(3)
_cell_angle_alpha                90
_cell_angle_beta                 115.971(4)
_cell_angle_gamma                90
_cell_volume                     2085.29(12)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    5834
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      30.1630
_cell_measurement_theta_min      2.3020
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.078
_exptl_absorpt_correction_T_max  0.982
_exptl_absorpt_correction_T_min  0.947
_exptl_absorpt_correction_type   analytical
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31h (release 21-03-2014 CrysAlis171 .NET)
(compiled Mar 21 2014,18:13:45)
Analytical numeric absorption correction using a multifaceted crystal
			model based on expressions derived by R.C. Clark & J.S. Reid.
(Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            green
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   .
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.421
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             932
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method 
'The material was recrystallised from water by slow evaporation'
_exptl_crystal_size_max          0.3103
_exptl_crystal_size_mid          0.1636
_exptl_crystal_size_min          0.0807
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0399
_diffrn_reflns_av_unetI/netI     0.0421
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            18063
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         28.000
_diffrn_reflns_theta_min         2.061
_diffrn_ambient_temperature      120(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1511
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -24.00   63.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       21.7633 -100.0000    0.0000 87

#__ type_ start__ end____ width___ exp.time_
  2 omega    0.00   92.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       21.7633   38.0000 -120.0000 92

#__ type_ start__ end____ width___ exp.time_
  3 omega   -7.00   91.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -       21.7633   77.0000  120.0000 98

#__ type_ start__ end____ width___ exp.time_
  4 omega  -40.00   35.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      -21.1383   57.0000 -120.0000 75

#__ type_ start__ end____ width___ exp.time_
  5 omega  -59.00   -9.00   1.0000   12.0000
omega____ theta____ kappa____ phi______ frames
    -      -21.1383   19.0000 -150.0000 50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0020620000
_diffrn_orient_matrix_UB_12      0.0324521000
_diffrn_orient_matrix_UB_13      0.0267807000
_diffrn_orient_matrix_UB_21      -0.0175044000
_diffrn_orient_matrix_UB_22      0.0146511000
_diffrn_orient_matrix_UB_23      -0.0646481000
_diffrn_orient_matrix_UB_31      -0.0713931000
_diffrn_orient_matrix_UB_32      -0.0045419000
_diffrn_orient_matrix_UB_33      -0.0174740000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_source_current           35
_diffrn_source_voltage           50
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4158
_reflns_number_total             5043
_reflns_odcompleteness_completeness 99.98
_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, Agilent Technologies,
Version 1.171.37.31h (release 21-03-2014 CrysAlis171 .NET)
(compiled Mar 21 2014,18:13:45)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31h (release 21-03-2014 CrysAlis171 .NET)
(compiled Mar 21 2014,18:13:45)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31h (release 21-03-2014 CrysAlis171 .NET)
(compiled Mar 21 2014,18:13:45)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2013)'
_refine_diff_density_max         0.494
_refine_diff_density_min         -0.477
_refine_diff_density_rms         0.103
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.058
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         5043
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0482
_refine_ls_R_factor_gt           0.0349
_refine_ls_restrained_S_all      1.058
_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)+(0.0319P)²+1.0231P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0780
_refine_ls_wR_factor_ref         0.0850
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C14(H14a,H14b), C8(H8a,H8b), C11(H11a,H11b), C9(H9a,H9b), C13(H13a,H13b),
 C12(H12a,H12b), C10(H10a,H10b)
2.b Aromatic/amide H refined with riding coordinates:
 C7(H7), C5(H5), C23(H23), C4(H4), C25(H25), C3(H3), C22(H22), C2(H2), C26(H26)
2.c Idealised Me refined as rotating group:
 C27(H27a,H27b,H27c)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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 0.41822(2) 0.67226(2) 0.76818(2) 0.01745(8) Uani 1 1 d . . . . .
O1 O 0.57066(14) 0.70929(7) 0.92182(15) 0.0248(3) Uani 1 1 d . . . . .
O2 O 0.39198(13) 0.59906(7) 0.87713(14) 0.0190(3) Uani 1 1 d . . . . .
O3 O 0.19288(14) 0.64562(7) 0.74058(15) 0.0228(3) Uani 1 1 d . . . . .
C6 C 0.6135(2) 0.80115(10) 0.8000(3) 0.0282(5) Uani 1 1 d . . . . .
N1 N 0.38832(18) 0.75266(8) 0.65979(17) 0.0212(4) Uani 1 1 d . . . . .
C7 C 0.4805(2) 0.79860(10) 0.6828(2) 0.0258(5) Uani 1 1 d . . . . .
H7 H 0.4594 0.8337 0.6174 0.031 Uiso 1 1 calc R . . . .
C5 C 0.7072(3) 0.85146(12) 0.8002(3) 0.0419(7) Uani 1 1 d . . . . .
H5 H 0.6816 0.8805 0.7237 0.050 Uiso 1 1 calc R . . . .
C23 C 0.1902(2) 0.43084(10) 0.9429(2) 0.0234(4) Uani 1 1 d . . . . .
H23 H 0.2411 0.3923 0.9909 0.028 Uiso 1 1 calc R . . . .
C4 C 0.8347(3) 0.85904(13) 0.9090(4) 0.0537(9) Uani 1 1 d . . . . .
H4 H 0.8975 0.8926 0.9076 0.064 Uiso 1 1 calc R . . . .
C25 C -0.0260(2) 0.48870(10) 0.8238(2) 0.0244(4) Uani 1 1 d . . . . .
H25 H -0.1238 0.4903 0.7913 0.029 Uiso 1 1 calc R . . . .
C1 C 0.6503(2) 0.75774(10) 0.9133(2) 0.0246(5) Uani 1 1 d . . . . .
C3 C 0.8709(3) 0.81721(13) 1.0208(3) 0.0490(8) Uani 1 1 d . . . . .
H3 H 0.9594 0.8221 1.0958 0.059 Uiso 1 1 calc R . . . .
C24 C 0.0469(2) 0.43236(10) 0.8962(2) 0.0233(4) Uani 1 1 d . . . . .
C21 C 0.1861(2) 0.54123(9) 0.84775(19) 0.0174(4) Uani 1 1 d . . . . .
C20 C 0.2592(2) 0.59925(9) 0.82032(19) 0.0174(4) Uani 1 1 d . . . . .
C22 C 0.2592(2) 0.48508(10) 0.9199(2) 0.0205(4) Uani 1 1 d . . . . .
H22 H 0.3572 0.4838 0.9538 0.025 Uiso 1 1 calc R . . . .
C2 C 0.7804(2) 0.76832(12) 1.0255(3) 0.0359(6) Uani 1 1 d . . . . .
H2 H 0.8062 0.7416 1.1050 0.043 Uiso 1 1 calc R . . . .
C26 C 0.0423(2) 0.54240(10) 0.7984(2) 0.0228(4) Uani 1 1 d . . . . .
H26 H -0.0090 0.5801 0.7472 0.027 Uiso 1 1 calc R . . . .
N2 N 0.38429(16) 0.61194(8) 0.59168(17) 0.0183(3) Uani 1 1 d . . . . .
C14 C 0.3759(2) 0.53762(9) 0.6119(2) 0.0207(4) Uani 1 1 d . . . . .
H14A H 0.3525 0.5138 0.5250 0.025 Uiso 1 1 calc R . . . .
H14B H 0.3012 0.5286 0.6396 0.025 Uiso 1 1 calc R . . . .
C8 C 0.2557(2) 0.75732(10) 0.5376(2) 0.0263(5) Uani 1 1 d . . . . .
H8A H 0.2455 0.8034 0.4988 0.032 Uiso 1 1 calc R . . . .
H8B H 0.1788 0.7500 0.5631 0.032 Uiso 1 1 calc R . . . .
C11 C 0.5024(2) 0.62284(10) 0.5571(2) 0.0237(4) Uani 1 1 d . . . . .
H11A H 0.5147 0.6719 0.5480 0.028 Uiso 1 1 calc R . . . .
H11B H 0.4817 0.6011 0.4688 0.028 Uiso 1 1 calc R . . . .
C9 C 0.2451(2) 0.70587(11) 0.4308(2) 0.0287(5) Uani 1 1 d . . . . .
H9A H 0.3214 0.7142 0.4049 0.034 Uiso 1 1 calc R . . . .
H9B H 0.1566 0.7132 0.3490 0.034 Uiso 1 1 calc R . . . .
C13 C 0.5115(2) 0.51080(10) 0.7191(2) 0.0244(4) Uani 1 1 d . . . . .
H13A H 0.5327 0.5331 0.8070 0.029 Uiso 1 1 calc R . . . .
H13B H 0.5029 0.4616 0.7306 0.029 Uiso 1 1 calc R . . . .
C12 C 0.6345(2) 0.59360(11) 0.6656(2) 0.0280(5) Uani 1 1 d . . . . .
H12A H 0.7115 0.6018 0.6406 0.034 Uiso 1 1 calc R . . . .
H12B H 0.6572 0.6170 0.7529 0.034 Uiso 1 1 calc R . . . .
C10 C 0.2517(2) 0.63210(11) 0.4743(2) 0.0253(4) Uani 1 1 d . . . . .
H10A H 0.1743 0.6235 0.4985 0.030 Uiso 1 1 calc R . . . .
H10B H 0.2373 0.6029 0.3958 0.030 Uiso 1 1 calc R . . . .
O4 O 0.62265(15) 0.52265(7) 0.68277(16) 0.0286(3) Uani 1 1 d . . . . .
C27 C -0.0286(2) 0.37416(11) 0.9236(2) 0.0302(5) Uani 1 1 d . . . . .
H27A H -0.0287 0.3351 0.8684 0.045 Uiso 1 1 calc GR . . . .
H27B H -0.1243 0.3876 0.9001 0.045 Uiso 1 1 calc GR . . . .
H27C H 0.0183 0.3620 1.0201 0.045 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 O1 1.9047(14) . y
Cu1 O4 1.9714(13) . y
Cu1 O3 2.3606(14) . y
Cu1 N1 1.9238(16) . y
Cu1 N2 2.1605(16) . y
O1 C1 1.313(2) . ?
O4 C20 1.281(2) . ?
O3 C20 1.250(2) . ?
C6 C7 1.442(3) . ?
C6 C5 1.413(3) . ?
C6 C1 1.414(3) . ?
N1 C7 1.283(3) . ?
N1 C8 1.468(3) . ?
C7 H7 0.9500 . ?
C5 H5 0.9500 . ?
C5 C4 1.373(4) . ?
C23 H23 0.9500 . ?
C23 C24 1.391(3) . ?
C23 C22 1.387(3) . ?
C4 H4 0.9500 . ?
C4 C3 1.383(4) . ?
C25 H25 0.9500 . ?
C25 C24 1.392(3) . ?
C25 C26 1.385(3) . ?
C1 C2 1.414(3) . ?
C3 H3 0.9500 . ?
C3 C2 1.386(3) . ?
C24 C27 1.510(3) . ?
C21 C20 1.492(3) . ?
C21 C22 1.388(3) . ?
C21 C26 1.393(3) . ?
C22 H22 0.9500 . ?
C2 H2 0.9500 . ?
C26 H26 0.9500 . ?
N2 C14 1.494(2) . ?
N2 C11 1.488(2) . ?
N2 C10 1.494(3) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C14 C13 1.509(3) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.515(3) . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.510(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.525(3) . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 O2 1.431(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C12 O2 1.427(2) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C27 H27A 0.9800 . ?
C27 H27B 0.9800 . ?
C27 H27C 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
O1 Cu1 O4 92.46(6) . . y
O1 Cu1 O3 129.34(6) . . y
O1 Cu1 N1 94.23(7) . . y
O1 Cu1 N2 138.11(6) . . y
O4 Cu1 O3 60.29(5) . . y
O4 Cu1 N2 97.07(6) . . y
N1 Cu1 O4 161.69(6) . . y
N1 Cu1 O3 102.73(6) . . y
N1 Cu1 N2 89.26(6) . . y
N2 Cu1 O3 90.02(6) . . y
C1 O1 Cu1 123.45(14) . . ?
C20 O4 Cu1 97.32(11) . . ?
C20 O3 Cu1 80.59(11) . . ?
C5 C6 C7 116.8(2) . . ?
C5 C6 C1 120.0(2) . . ?
C1 C6 C7 123.12(19) . . ?
C7 N1 Cu1 123.86(15) . . ?
C7 N1 C8 119.38(18) . . ?
C8 N1 Cu1 116.53(13) . . ?
C6 C7 H7 117.4 . . ?
N1 C7 C6 125.2(2) . . ?
N1 C7 H7 117.4 . . ?
C6 C5 H5 119.5 . . ?
C4 C5 C6 121.0(3) . . ?
C4 C5 H5 119.5 . . ?
C24 C23 H23 119.7 . . ?
C22 C23 H23 119.7 . . ?
C22 C23 C24 120.57(19) . . ?
C5 C4 H4 120.4 . . ?
C5 C4 C3 119.3(2) . . ?
C3 C4 H4 120.4 . . ?
C24 C25 H25 119.6 . . ?
C26 C25 H25 119.6 . . ?
C26 C25 C24 120.84(19) . . ?
O1 C1 C6 124.3(2) . . ?
O1 C1 C2 118.2(2) . . ?
C2 C1 C6 117.5(2) . . ?
C4 C3 H3 119.4 . . ?
C4 C3 C2 121.3(3) . . ?
C2 C3 H3 119.4 . . ?
C23 C24 C25 118.75(18) . . ?
C23 C24 C27 120.86(19) . . ?
C25 C24 C27 120.39(19) . . ?
C22 C21 C20 120.84(17) . . ?
C22 C21 C26 119.19(18) . . ?
C26 C21 C20 119.95(17) . . ?
O4 C20 C21 118.10(17) . . ?
O3 C20 O4 120.85(17) . . ?
O3 C20 C21 121.01(17) . . ?
C23 C22 C21 120.47(18) . . ?
C23 C22 H22 119.8 . . ?
C21 C22 H22 119.8 . . ?
C1 C2 H2 119.6 . . ?
C3 C2 C1 120.8(3) . . ?
C3 C2 H2 119.6 . . ?
C25 C26 C21 120.16(19) . . ?
C25 C26 H26 119.9 . . ?
C21 C26 H26 119.9 . . ?
C14 N2 Cu1 114.06(12) . . ?
C14 N2 C10 107.04(15) . . ?
C11 N2 Cu1 108.58(12) . . ?
C11 N2 C14 107.03(15) . . ?
C11 N2 C10 109.82(16) . . ?
C10 N2 Cu1 110.22(12) . . ?
N2 C14 H14A 109.4 . . ?
N2 C14 H14B 109.4 . . ?
N2 C14 C13 111.11(16) . . ?
H14A C14 H14B 108.0 . . ?
C13 C14 H14A 109.4 . . ?
C13 C14 H14B 109.4 . . ?
N1 C8 H8A 109.2 . . ?
N1 C8 H8B 109.2 . . ?
N1 C8 C9 112.05(17) . . ?
H8A C8 H8B 107.9 . . ?
C9 C8 H8A 109.2 . . ?
C9 C8 H8B 109.2 . . ?
N2 C11 H11A 109.5 . . ?
N2 C11 H11B 109.5 . . ?
N2 C11 C12 110.81(17) . . ?
H11A C11 H11B 108.1 . . ?
C12 C11 H11A 109.5 . . ?
C12 C11 H11B 109.5 . . ?
C8 C9 H9A 108.5 . . ?
C8 C9 H9B 108.5 . . ?
C8 C9 C10 115.03(17) . . ?
H9A C9 H9B 107.5 . . ?
C10 C9 H9A 108.5 . . ?
C10 C9 H9B 108.5 . . ?
C14 C13 H13A 109.4 . . ?
C14 C13 H13B 109.4 . . ?
H13A C13 H13B 108.0 . . ?
O2 C13 C14 111.31(17) . . ?
O2 C13 H13A 109.4 . . ?
O2 C13 H13B 109.4 . . ?
C11 C12 H12A 109.2 . . ?
C11 C12 H12B 109.2 . . ?
H12A C12 H12B 107.9 . . ?
O2 C12 C11 111.85(17) . . ?
O2 C12 H12A 109.2 . . ?
O2 C12 H12B 109.2 . . ?
N2 C10 C9 114.79(17) . . ?
N2 C10 H10A 108.6 . . ?
N2 C10 H10B 108.6 . . ?
C9 C10 H10A 108.6 . . ?
C9 C10 H10B 108.6 . . ?
H10A C10 H10B 107.5 . . ?
C12 O2 C13 109.28(15) . . ?
C24 C27 H27A 109.5 . . ?
C24 C27 H27B 109.5 . . ?
C24 C27 H27C 109.5 . . ?
H27A C27 H27B 109.5 . . ?
H27A C27 H27C 109.5 . . ?
H27B C27 H27C 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 O1 C1 C6 18.5(3) . . . . ?
Cu1 O1 C1 C2 -162.79(15) . . . . ?
Cu1 O4 C20 O3 -10.67(19) . . . . ?
Cu1 O4 C20 C21 166.95(14) . . . . ?
Cu1 O3 C20 O4 8.94(16) . . . . ?
Cu1 O3 C20 C21 -168.61(17) . . . . ?
Cu1 N1 C7 C6 -7.2(3) . . . . ?
Cu1 N1 C8 C9 -68.0(2) . . . . ?
Cu1 N2 C14 C13 -63.84(18) . . . . ?
Cu1 N2 C11 C12 67.59(17) . . . . ?
Cu1 N2 C10 C9 59.95(19) . . . . ?
O1 C1 C2 C3 177.9(2) . . . . ?
C6 C5 C4 C3 -0.8(4) . . . . ?
C6 C1 C2 C3 -3.3(3) . . . . ?
N1 C8 C9 C10 61.8(2) . . . . ?
C7 C6 C5 C4 178.1(2) . . . . ?
C7 C6 C1 O1 2.7(3) . . . . ?
C7 C6 C1 C2 -175.99(19) . . . . ?
C7 N1 C8 C9 106.7(2) . . . . ?
C5 C6 C7 N1 173.2(2) . . . . ?
C5 C6 C1 O1 -179.40(19) . . . . ?
C5 C6 C1 C2 1.9(3) . . . . ?
C5 C4 C3 C2 -0.6(4) . . . . ?
C4 C3 C2 C1 2.7(4) . . . . ?
C1 C6 C7 N1 -8.9(3) . . . . ?
C1 C6 C5 C4 0.1(3) . . . . ?
C24 C23 C22 C21 -1.2(3) . . . . ?
C24 C25 C26 C21 -1.3(3) . . . . ?
C20 C21 C22 C23 -178.86(18) . . . . ?
C20 C21 C26 C25 -179.91(18) . . . . ?
C22 C23 C24 C25 1.3(3) . . . . ?
C22 C23 C24 C27 -178.62(19) . . . . ?
C22 C21 C20 O4 -7.2(3) . . . . ?
C22 C21 C20 O3 170.38(18) . . . . ?
C22 C21 C26 C25 1.4(3) . . . . ?
C26 C25 C24 C23 -0.1(3) . . . . ?
C26 C25 C24 C27 179.85(19) . . . . ?
C26 C21 C20 O4 174.05(17) . . . . ?
C26 C21 C20 O3 -8.3(3) . . . . ?
C26 C21 C22 C23 -0.1(3) . . . . ?
N2 C14 C13 O2 -59.3(2) . . . . ?
N2 C11 C12 O2 59.3(2) . . . . ?
C14 N2 C11 C12 -56.0(2) . . . . ?
C14 N2 C10 C9 -175.49(17) . . . . ?
C14 C13 O2 C12 58.8(2) . . . . ?
C8 N1 C7 C6 178.46(18) . . . . ?
C8 C9 C10 N2 -62.3(2) . . . . ?
C11 N2 C14 C13 56.3(2) . . . . ?
C11 N2 C10 C9 -59.6(2) . . . . ?
C11 C12 O2 C13 -59.0(2) . . . . ?
C10 N2 C14 C13 173.98(16) . . . . ?
C10 N2 C11 C12 -171.84(16) . . . . ?

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-15 -1 3 0.1380 -14.6919 -1.2864 3.3208 0.0775 0.0236 0.9967
-1 27 4 0.0460 -1.4960 27.0471 3.6900 0.9796 0.1839 -0.0805
15 -2 -4 0.1585 14.7663 -1.8512 -3.7254 -0.1903 -0.0448 -0.9807
1 -27 -4 0.0264 0.7149 -27.0773 -3.5087 -0.9742 -0.1824 0.1333
-14 -2 0 0.1205 -13.6820 -1.9456 0.2770 -0.0275 0.1931 0.9808
-1 -6 14 0.0644 -1.1353 -6.0137 14.0067 0.1823 -0.9737 -0.1364
15 4 -5 0.1590 14.8868 4.2415 -5.3778 -0.0371 0.1492 -0.9881
5 7 -15 0.0712 5.0063 6.8904 -14.8644 -0.1848 0.9743 -0.1290

_olex2_computing_structure_refinement_long 'ShelXL (Sheldrick, 2008)'
_olex2_exptl_crystal_mounting_method 
'The crystal was mounted on a hair in perfluoroether oil'
####################################################################### 
# 
# 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_icvu_185
_database_code_depnum_ccdc_archive 'CCDC 1405167'
_audit_update_record             
;
2015-06-05 deposited with the CCDC.
2016-06-10 downloaded from the CCDC.
;
_audit_creation_date             2014-03-06
_audit_creation_method           
;
Olex2 1.2-ac21
(compiled 2014.02.17 svn.r2891 for OlexSys, GUI svn.r3563)
;
_shelxl_version_number           2013-2
_chemical_name_common            ?
_chemical_name_systematic        
;
 ?
;
_chemical_formula_moiety         'C23 H26 Cu N2 O4'
_chemical_formula_sum            'C23 H26 Cu N2 O4'
_chemical_formula_weight         458.00
_chemical_melting_point          ?
_chemical_oxdiff_formula         C23H27CuN3O3
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                   10.2427(3)
_cell_length_b                   24.3438(6)
_cell_length_c                   9.3982(4)
_cell_angle_alpha                90
_cell_angle_beta                 114.260(4)
_cell_angle_gamma                90
_cell_volume                     2136.45(13)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6522
_cell_measurement_temperature    120(2)
_cell_measurement_theta_max      30.4660
_cell_measurement_theta_min      1.7150
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    1.054
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.67839
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'dark green'
_exptl_crystal_colour_lustre     .
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    green
_exptl_crystal_density_diffrn    1.424
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             956
_exptl_crystal_preparation       ?
_exptl_crystal_recrystallization_method 
'The material was recrystallised from water by slow evaporation'
_exptl_crystal_size_max          0.3836
_exptl_crystal_size_mid          0.2545
_exptl_crystal_size_min          0.1138
_exptl_special_details           
;
 ?
;
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0318
_diffrn_reflns_av_unetI/netI     0.0309
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       31
_diffrn_reflns_limit_k_min       -32
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            17742
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        26.000
_diffrn_reflns_theta_max         28.497
_diffrn_reflns_theta_min         2.181
_diffrn_ambient_temperature      120(2)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 16.1511
_diffrn_detector_type            Sapphire3
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega  -29.00    8.00   1.0000   14.2250
omega____ theta____ kappa____ phi______ frames
    -       21.7633  119.0000  -41.3172 37

#__ type_ start__ end____ width___ exp.time_
  2 omega  -16.00   94.00   1.0000   14.2250
omega____ theta____ kappa____ phi______ frames
    -       21.7633   19.0000   30.0000 110

#__ type_ start__ end____ width___ exp.time_
  3 omega  -16.00   94.00   1.0000   14.2250
omega____ theta____ kappa____ phi______ frames
    -       21.7633   19.0000  120.0000 110

#__ type_ start__ end____ width___ exp.time_
  4 omega  -90.00   -3.00   1.0000   14.2250
omega____ theta____ kappa____ phi______ frames
    -      -21.1383  -57.0000 -150.0000 87

#__ type_ start__ end____ width___ exp.time_
  5 omega  -96.00  -65.00   1.0000   14.2250
omega____ theta____ kappa____ phi______ frames
    -      -21.1383  178.0000 -180.0000 31
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'Xcalibur, Sapphire3'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_UB_11      -0.0341968000
_diffrn_orient_matrix_UB_12      0.0104678000
_diffrn_orient_matrix_UB_13      -0.0770220000
_diffrn_orient_matrix_UB_21      -0.0676527000
_diffrn_orient_matrix_UB_22      -0.0032158000
_diffrn_orient_matrix_UB_23      0.0030141000
_diffrn_orient_matrix_UB_31      0.0051955000
_diffrn_orient_matrix_UB_32      0.0270002000
_diffrn_orient_matrix_UB_33      0.0301652000
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'Enhance (Mo) X-ray Source'
_diffrn_special_details          ?
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                4714
_reflns_number_total             5408
_reflns_odcompleteness_completeness 99.98
_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, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.31 (release 14-01-2014 CrysAlis171 .NET)
(compiled Jan 14 2014,18:38:05)
;
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2008)'
_computing_structure_solution    'olex2.solve (Bourhis et al., 2013)'
_refine_diff_density_max         0.578
_refine_diff_density_min         -0.410
_refine_diff_density_rms         0.063
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         5408
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0417
_refine_ls_R_factor_gt           0.0343
_refine_ls_restrained_S_all      1.023
_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)+(0.0335P)²+1.6211P]
 where P=(Fo²+2Fc²)/3
;
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0782
_refine_ls_wR_factor_ref         0.0816
_refine_special_details          
;
 ?
;
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B), C9(H9A,H9B), C10(H10A,H10B), C11(H11A,H11B), C12(H12A,H12B),
 C13(H13A,H13B), C14(H14A,H14B)
2.b Aromatic/amide H refined with riding coordinates:
 C2(H2), C3(H3), C4(H4), C5(H5), C7(H7), C21(H21), C22(H22), C24(H24),
 C25(H25), C26(H26), C27(H27), C28(H28)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     iterative
_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 0.55126(2) 0.16352(2) 0.92028(2) 0.01634(7) Uani 1 1 d . . . . .
O1 O 0.37895(13) 0.19113(5) 0.92153(16) 0.0246(3) Uani 1 1 d . . . . .
O2 O 0.56906(12) 0.10828(5) 1.08497(14) 0.0191(3) Uani 1 1 d . . . . .
O3 O 0.77142(13) 0.15260(5) 1.13749(15) 0.0227(3) Uani 1 1 d . . . . .
O4 O 0.38956(17) 0.03415(6) 0.63482(17) 0.0383(4) Uani 1 1 d . . . . .
N1 N 0.59722(15) 0.23035(6) 0.83984(18) 0.0192(3) Uani 1 1 d . . . . .
N2 N 0.61620(15) 0.11372(6) 0.77615(17) 0.0196(3) Uani 1 1 d . . . . .
C1 C 0.31328(17) 0.23636(7) 0.8549(2) 0.0187(3) Uani 1 1 d . . . . .
C2 C 0.17479(19) 0.24688(8) 0.8495(2) 0.0252(4) Uani 1 1 d . . . . .
H2 H 0.1341 0.2216 0.8968 0.030 Uiso 1 1 calc R . . . .
C3 C 0.09847(19) 0.29294(8) 0.7771(2) 0.0261(4) Uani 1 1 d . . . . .
H3 H 0.0047 0.2982 0.7718 0.031 Uiso 1 1 calc R . . . .
C4 C 0.1563(2) 0.33193(8) 0.7114(2) 0.0276(4) Uani 1 1 d . . . . .
H4 H 0.1028 0.3636 0.6618 0.033 Uiso 1 1 calc R . . . .
C5 C 0.2918(2) 0.32406(7) 0.7193(2) 0.0244(4) Uani 1 1 d . . . . .
H5 H 0.3328 0.3512 0.6774 0.029 Uiso 1 1 calc R . . . .
C6 C 0.37160(18) 0.27640(7) 0.78858(19) 0.0180(3) Uani 1 1 d . . . . .
C7 C 0.51279(18) 0.27190(7) 0.7911(2) 0.0190(3) Uani 1 1 d . . . . .
H7 H 0.5467 0.3025 0.7532 0.023 Uiso 1 1 calc R . . . .
C8 C 0.74223(19) 0.23414(8) 0.8439(2) 0.0262(4) Uani 1 1 d . . . . .
H8A H 0.8137 0.2292 0.9526 0.031 Uiso 1 1 calc R . . . .
H8B H 0.7560 0.2712 0.8087 0.031 Uiso 1 1 calc R . . . .
C9 C 0.7672(2) 0.19133(9) 0.7410(2) 0.0294(4) Uani 1 1 d . . . . .
H9A H 0.8625 0.1978 0.7407 0.035 Uiso 1 1 calc R . . . .
H9B H 0.6947 0.1964 0.6328 0.035 Uiso 1 1 calc R . . . .
C10 C 0.7604(2) 0.13212(8) 0.7896(2) 0.0266(4) Uani 1 1 d . . . . .
H10A H 0.7907 0.1077 0.7244 0.032 Uiso 1 1 calc R . . . .
H10B H 0.8301 0.1275 0.8993 0.032 Uiso 1 1 calc R . . . .
C11 C 0.5102(2) 0.11729(9) 0.6106(2) 0.0277(4) Uani 1 1 d . . . . .
H11A H 0.5488 0.0986 0.5426 0.033 Uiso 1 1 calc R . . . .
H11B H 0.4933 0.1563 0.5786 0.033 Uiso 1 1 calc R . . . .
C12 C 0.3711(2) 0.09084(9) 0.5912(2) 0.0331(5) Uani 1 1 d . . . . .
H12A H 0.3311 0.1105 0.6565 0.040 Uiso 1 1 calc R . . . .
H12B H 0.3017 0.0941 0.4810 0.040 Uiso 1 1 calc R . . . .
C13 C 0.4865(2) 0.03046(8) 0.7959(2) 0.0301(4) Uani 1 1 d . . . . .
H13A H 0.4993 -0.0086 0.8285 0.036 Uiso 1 1 calc R . . . .
H13B H 0.4457 0.0501 0.8604 0.036 Uiso 1 1 calc R . . . .
C14 C 0.6294(2) 0.05495(7) 0.8226(2) 0.0253(4) Uani 1 1 d . . . . .
H14A H 0.6946 0.0517 0.9345 0.030 Uiso 1 1 calc R . . . .
H14B H 0.6719 0.0342 0.7616 0.030 Uiso 1 1 calc R . . . .
C20 C 0.70057(17) 0.11786(7) 1.17442(19) 0.0159(3) Uani 1 1 d . . . . .
C21 C 0.76479(18) 0.08783(7) 1.3243(2) 0.0177(3) Uani 1 1 d . . . . .
H21 H 0.7139 0.0581 1.3433 0.021 Uiso 1 1 calc R . . . .
C22 C 0.89251(18) 0.10170(7) 1.4331(2) 0.0177(3) Uani 1 1 d . . . . .
H22 H 0.9411 0.1308 1.4079 0.021 Uiso 1 1 calc R . . . .
C23 C 0.96608(17) 0.07678(7) 1.58766(19) 0.0180(3) Uani 1 1 d . . . . .
C24 C 1.07662(19) 0.10590(8) 1.7026(2) 0.0242(4) Uani 1 1 d . . . . .
H24 H 1.1058 0.1402 1.6773 0.029 Uiso 1 1 calc R . . . .
C25 C 1.1445(2) 0.08561(9) 1.8528(2) 0.0314(5) Uani 1 1 d . . . . .
H25 H 1.2190 0.1060 1.9302 0.038 Uiso 1 1 calc R . . . .
C26 C 1.1032(2) 0.03546(9) 1.8896(2) 0.0335(5) Uani 1 1 d . . . . .
H26 H 1.1484 0.0217 1.9930 0.040 Uiso 1 1 calc R . . . .
C27 C 0.9960(2) 0.00514(8) 1.7759(2) 0.0297(4) Uani 1 1 d . . . . .
H27 H 0.9695 -0.0297 1.8014 0.036 Uiso 1 1 calc R . . . .
C28 C 0.9272(2) 0.02552(7) 1.6251(2) 0.0222(4) Uani 1 1 d . . . . .
H28 H 0.8539 0.0047 1.5476 0.027 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 O1 1.8931(12) . y
Cu1 O2 2.0013(12) . y
Cu1 N1 1.9320(14) . y
Cu1 N2 2.1183(15) . y
O1 C1 1.308(2) . ?
O2 C20 1.283(2) . ?
O3 C20 1.253(2) . ?
O4 C12 1.430(3) . ?
O4 C13 1.432(2) . ?
N1 C7 1.286(2) . ?
N1 C8 1.473(2) . ?
N2 C10 1.498(2) . ?
N2 C11 1.489(2) . ?
N2 C14 1.486(2) . ?
C1 C2 1.422(2) . ?
C1 C6 1.415(2) . ?
C2 H2 0.9500 . ?
C2 C3 1.376(3) . ?
C3 H3 0.9500 . ?
C3 C4 1.390(3) . ?
C4 H4 0.9500 . ?
C4 C5 1.373(3) . ?
C5 H5 0.9500 . ?
C5 C6 1.414(2) . ?
C6 C7 1.441(2) . ?
C7 H7 0.9500 . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C8 C9 1.513(3) . ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C9 C10 1.522(3) . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 H11A 0.9900 . ?
C11 H11B 0.9900 . ?
C11 C12 1.505(3) . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 H13A 0.9900 . ?
C13 H13B 0.9900 . ?
C13 C14 1.503(3) . ?
C14 H14A 0.9900 . ?
C14 H14B 0.9900 . ?
C20 C21 1.480(2) . ?
C21 H21 0.9500 . ?
C21 C22 1.331(2) . ?
C22 H22 0.9500 . ?
C22 C23 1.465(2) . ?
C23 C24 1.395(2) . ?
C23 C28 1.398(3) . ?
C24 H24 0.9500 . ?
C24 C25 1.383(3) . ?
C25 H25 0.9500 . ?
C25 C26 1.381(3) . ?
C26 H26 0.9500 . ?
C26 C27 1.389(3) . ?
C27 H27 0.9500 . ?
C27 C28 1.390(3) . ?
C28 H28 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
O1 Cu1 O2 91.30(5) . . y
O1 Cu1 N1 94.65(6) . . y
O1 Cu1 N2 138.22(6) . . y
O2 Cu1 N2 99.05(5) . . y
N1 Cu1 O2 155.37(6) . . y
N1 Cu1 N2 92.34(6) . . y
C1 O1 Cu1 126.38(11) . . ?
C20 O2 Cu1 97.02(10) . . ?
C12 O4 C13 108.43(15) . . ?
C7 N1 Cu1 124.42(12) . . ?
C7 N1 C8 118.88(15) . . ?
C8 N1 Cu1 116.61(11) . . ?
C10 N2 Cu1 109.43(11) . . ?
C11 N2 Cu1 110.41(11) . . ?
C11 N2 C10 109.94(15) . . ?
C14 N2 Cu1 112.18(11) . . ?
C14 N2 C10 107.20(14) . . ?
C14 N2 C11 107.61(14) . . ?
O1 C1 C2 118.55(16) . . ?
O1 C1 C6 124.32(15) . . ?
C6 C1 C2 117.13(15) . . ?
C1 C2 H2 119.3 . . ?
C3 C2 C1 121.33(18) . . ?
C3 C2 H2 119.3 . . ?
C2 C3 H3 119.4 . . ?
C2 C3 C4 121.10(17) . . ?
C4 C3 H3 119.4 . . ?
C3 C4 H4 120.4 . . ?
C5 C4 C3 119.12(17) . . ?
C5 C4 H4 120.4 . . ?
C4 C5 H5 119.4 . . ?
C4 C5 C6 121.30(18) . . ?
C6 C5 H5 119.4 . . ?
C1 C6 C7 122.90(15) . . ?
C5 C6 C1 119.96(16) . . ?
C5 C6 C7 117.13(16) . . ?
N1 C7 C6 126.07(16) . . ?
N1 C7 H7 117.0 . . ?
C6 C7 H7 117.0 . . ?
N1 C8 H8A 109.2 . . ?
N1 C8 H8B 109.2 . . ?
N1 C8 C9 111.95(15) . . ?
H8A C8 H8B 107.9 . . ?
C9 C8 H8A 109.2 . . ?
C9 C8 H8B 109.2 . . ?
C8 C9 H9A 108.6 . . ?
C8 C9 H9B 108.6 . . ?
C8 C9 C10 114.84(16) . . ?
H9A C9 H9B 107.5 . . ?
C10 C9 H9A 108.6 . . ?
C10 C9 H9B 108.6 . . ?
N2 C10 C9 115.02(15) . . ?
N2 C10 H10A 108.5 . . ?
N2 C10 H10B 108.5 . . ?
C9 C10 H10A 108.5 . . ?
C9 C10 H10B 108.5 . . ?
H10A C10 H10B 107.5 . . ?
N2 C11 H11A 109.6 . . ?
N2 C11 H11B 109.6 . . ?
N2 C11 C12 110.45(16) . . ?
H11A C11 H11B 108.1 . . ?
C12 C11 H11A 109.6 . . ?
C12 C11 H11B 109.6 . . ?
O4 C12 C11 111.77(17) . . ?
O4 C12 H12A 109.3 . . ?
O4 C12 H12B 109.3 . . ?
C11 C12 H12A 109.3 . . ?
C11 C12 H12B 109.3 . . ?
H12A C12 H12B 107.9 . . ?
O4 C13 H13A 109.5 . . ?
O4 C13 H13B 109.5 . . ?
O4 C13 C14 110.88(17) . . ?
H13A C13 H13B 108.1 . . ?
C14 C13 H13A 109.5 . . ?
C14 C13 H13B 109.5 . . ?
N2 C14 C13 111.60(15) . . ?
N2 C14 H14A 109.3 . . ?
N2 C14 H14B 109.3 . . ?
C13 C14 H14A 109.3 . . ?
C13 C14 H14B 109.3 . . ?
H14A C14 H14B 108.0 . . ?
O2 C20 C21 118.07(15) . . ?
O3 C20 O2 120.87(15) . . ?
O3 C20 C21 121.04(15) . . ?
C20 C21 H21 119.4 . . ?
C22 C21 C20 121.21(15) . . ?
C22 C21 H21 119.4 . . ?
C21 C22 H22 116.6 . . ?
C21 C22 C23 126.83(16) . . ?
C23 C22 H22 116.6 . . ?
C24 C23 C22 118.73(16) . . ?
C24 C23 C28 118.88(16) . . ?
C28 C23 C22 122.37(16) . . ?
C23 C24 H24 119.5 . . ?
C25 C24 C23 121.09(19) . . ?
C25 C24 H24 119.5 . . ?
C24 C25 H25 120.2 . . ?
C26 C25 C24 119.58(19) . . ?
C26 C25 H25 120.2 . . ?
C25 C26 H26 119.9 . . ?
C25 C26 C27 120.28(18) . . ?
C27 C26 H26 119.9 . . ?
C26 C27 H27 119.9 . . ?
C26 C27 C28 120.26(19) . . ?
C28 C27 H27 119.9 . . ?
C23 C28 H28 120.1 . . ?
C27 C28 C23 119.88(18) . . ?
C27 C28 H28 120.1 . . ?

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 O1 C1 C2 171.45(13) . . . . ?
Cu1 O1 C1 C6 -9.4(3) . . . . ?
Cu1 O2 C20 O3 -1.75(17) . . . . ?
Cu1 O2 C20 C21 176.56(13) . . . . ?
Cu1 N1 C7 C6 0.5(3) . . . . ?
Cu1 N1 C8 C9 63.87(18) . . . . ?
Cu1 N2 C10 C9 -60.11(18) . . . . ?
Cu1 N2 C11 C12 -67.93(18) . . . . ?
Cu1 N2 C14 C13 66.36(17) . . . . ?
O1 C1 C2 C3 -178.12(17) . . . . ?
O1 C1 C6 C5 -179.89(17) . . . . ?
O1 C1 C6 C7 -1.5(3) . . . . ?
O2 Cu1 O1 C1 168.26(15) . . . . ?
O2 C20 C21 C22 -169.42(16) . . . . ?
O3 C20 C21 C22 8.9(3) . . . . ?
O4 C13 C14 N2 59.4(2) . . . . ?
N1 Cu1 O1 C1 12.19(16) . . . . ?
N1 C8 C9 C10 -63.3(2) . . . . ?
N2 Cu1 O1 C1 -86.58(17) . . . . ?
N2 C11 C12 O4 -59.7(2) . . . . ?
C1 C2 C3 C4 -2.4(3) . . . . ?
C1 C6 C7 N1 6.2(3) . . . . ?
C2 C1 C6 C5 -0.7(3) . . . . ?
C2 C1 C6 C7 177.71(17) . . . . ?
C2 C3 C4 C5 0.1(3) . . . . ?
C3 C4 C5 C6 1.9(3) . . . . ?
C4 C5 C6 C1 -1.6(3) . . . . ?
C4 C5 C6 C7 179.95(17) . . . . ?
C5 C6 C7 N1 -175.38(18) . . . . ?
C6 C1 C2 C3 2.6(3) . . . . ?
C7 N1 C8 C9 -119.40(18) . . . . ?
C8 N1 C7 C6 -175.93(17) . . . . ?
C8 C9 C10 N2 65.8(2) . . . . ?
C10 N2 C11 C12 171.23(16) . . . . ?
C10 N2 C14 C13 -173.49(16) . . . . ?
C11 N2 C10 C9 61.3(2) . . . . ?
C11 N2 C14 C13 -55.3(2) . . . . ?
C12 O4 C13 C14 -60.1(2) . . . . ?
C13 O4 C12 C11 60.8(2) . . . . ?
C14 N2 C10 C9 177.99(16) . . . . ?
C14 N2 C11 C12 54.8(2) . . . . ?
C20 C21 C22 C23 177.89(16) . . . . ?
C21 C22 C23 C24 -161.17(18) . . . . ?
C21 C22 C23 C28 17.2(3) . . . . ?
C22 C23 C24 C25 176.50(17) . . . . ?
C22 C23 C28 C27 -176.73(17) . . . . ?
C23 C24 C25 C26 0.6(3) . . . . ?
C24 C23 C28 C27 1.7(3) . . . . ?
C24 C25 C26 C27 1.1(3) . . . . ?
C25 C26 C27 C28 -1.4(3) . . . . ?
C26 C27 C28 C23 -0.1(3) . . . . ?
C28 C23 C24 C25 -2.0(3) . . . . ?

loop_
_exptl_crystal_face_index_h
_exptl_crystal_face_index_k
_exptl_crystal_face_index_l
_exptl_crystal_face_perp_dist
_exptl_oxdiff_crystal_face_indexfrac_h
_exptl_oxdiff_crystal_face_indexfrac_k
_exptl_oxdiff_crystal_face_indexfrac_l
_exptl_oxdiff_crystal_face_x
_exptl_oxdiff_crystal_face_y
_exptl_oxdiff_crystal_face_z
-13 -10 0 0.0569 -12.6133 -10.2718 0.1249 0.3142 0.8867 -0.3391
13 10 0 0.0568 12.6061 10.3079 -0.1184 -0.3141 -0.8863 0.3402
-3 17 11 0.1417 -3.4590 16.5568 11.4889 -0.5933 0.2154 0.7756
0 34 0 0.1161 0.1196 34.3196 -0.1091 0.3636 -0.1188 0.9240
4 -7 -13 0.1701 3.9064 -6.5698 -12.8748 0.7893 -0.2820 -0.5455
0 -34 0 0.1121 -0.2300 -34.2988 0.4715 -0.3875 0.1273 -0.9130
-3 -21 10 0.1332 -3.2238 -20.9001 10.4076 -0.9101 0.3167 -0.2671
2 -5 -1 0.1206 1.9984 -4.9990 -0.9989 -0.0437 -0.1221 -0.1547
-2 5 1 0.1206 -1.9984 4.9990 0.9989 0.0437 0.1221 0.1547

_olex2_computing_structure_refinement_long 'ShelXL (Sheldrick, 2008)'
