# Electronic Supplementary Material (ESI) for Chemical Communications.
# 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_nrc008
_database_code_depnum_ccdc_archive 'CCDC 1413561'
_audit_update_record             
;
2015-07-17 deposited with the CCDC.
2016-01-04 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C20 H28 Cu N2 O4'
_chemical_formula_weight         423.98

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'
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'
Cu Cu 0.3201 1.2651 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'

_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, -z'

_cell_length_a                   7.5787(2)
_cell_length_b                   8.0875(2)
_cell_length_c                   9.6138(3)
_cell_angle_alpha                72.4479(15)
_cell_angle_beta                 68.0319(15)
_cell_angle_gamma                85.0439(16)
_cell_volume                     520.80(3)
_cell_formula_units_Z            1
_cell_measurement_temperature    200(2)
_cell_measurement_reflns_used    4435
_cell_measurement_theta_min      2.39
_cell_measurement_theta_max      28.36

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_density_meas      n/a
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.352
_exptl_crystal_F_000             223
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    1.075
_shelx_estimated_absorpt_T_min   0.686
_shelx_estimated_absorpt_T_max   0.814
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6130
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_process_details   'SADABS, Bruker (2003)'

_exptl_special_details           
; 
 Data collection is performed with four batch runs at phi = 0.00 deg 
 (600 frames), at phi = 90.00 deg (600 frames), at phi = 180.00 deg 
 (600 frames), and at phi = 270.00 deg (600 frames). 
 A fifth batch run is collected at phi = 0.00 deg (50 frames) to monitor 
 crystal and diffractometer stability. Frame width = 0.30 deg in omega. 
 Data is merged, corrected for decay (if any), and treated with multi-scan 
 absorption corrections (if required). All symmetry-equivalent reflections 
 are merged for centrosymmetric data. 
 Friedel pairs are not merged for noncentrosymmetric data. 
;

_diffrn_ambient_temperature      200(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   ?
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            5143
_diffrn_reflns_av_unetI/netI     0.0163
_diffrn_reflns_av_R_equivalents  0.0121
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         2.388
_diffrn_reflns_theta_max         28.365
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.969
_diffrn_measured_fraction_theta_full 0.975
_diffrn_reflns_Laue_measured_fraction_max 0.969
_diffrn_reflns_Laue_measured_fraction_full 0.975
_diffrn_reflns_point_group_measured_fraction_max 0.969
_diffrn_reflns_point_group_measured_fraction_full 0.975
_reflns_number_total             2524
_reflns_number_gt                2451
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       'APEX II, Bruker (2009)'
_computing_cell_refinement       'APEX II, Bruker (2009)'
_computing_data_reduction        'XPREP, Bruker (2009)'
_computing_structure_solution    'SHELXS-03 (Sheldrick, 2003)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'SHELXTL, Bruker (2004)'
_computing_publication_material  'SHELXTL, Bruker (2004)'

_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)+(0.0537P)²+0.0362P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2524
_refine_ls_number_parameters     124
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0259
_refine_ls_R_factor_gt           0.0251
_refine_ls_wR_factor_ref         0.0722
_refine_ls_wR_factor_gt          0.0717
_refine_ls_goodness_of_fit_ref   1.052
_refine_ls_restrained_S_all      1.052
_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 1.0000 0.5000 0.0000 0.02841(9) Uani 1 2 d S . P . .
O1 O 0.86513(13) 0.60442(12) -0.14319(11) 0.0360(2) Uani 1 1 d . . . . .
O2 O 1.05770(18) 0.43757(16) -0.27768(15) 0.0543(3) Uani 1 1 d . . . . .
N1 N 0.82470(14) 0.29033(13) 0.09556(12) 0.0286(2) Uani 1 1 d . . . . .
C1 C 0.93314(19) 0.54376(18) -0.26020(17) 0.0389(3) Uani 1 1 d . . . . .
H1A H 0.8823 0.5849 -0.3406 0.047 Uiso 1 1 calc R U . . .
C2 C 0.64056(17) 0.30381(15) 0.11582(14) 0.0295(2) Uani 1 1 d . . . . .
H2A H 0.5937 0.4157 0.0825 0.035 Uiso 1 1 calc R U . . .
C3 C 0.51473(16) 0.16287(16) 0.18289(14) 0.0292(2) Uani 1 1 d . . . . .
H3A H 0.3845 0.1795 0.1960 0.035 Uiso 1 1 calc R U . . .
C4 C 0.57849(16) -0.00359(15) 0.23133(13) 0.0269(2) Uani 1 1 d . . . . .
C5 C 0.77187(17) -0.01696(15) 0.20705(15) 0.0326(2) Uani 1 1 d . . . . .
H5A H 0.8235 -0.1276 0.2360 0.039 Uiso 1 1 calc R U . . .
C6 C 0.88831(17) 0.13017(16) 0.14112(16) 0.0341(3) Uani 1 1 d . . . . .
H6A H 1.0191 0.1178 0.1273 0.041 Uiso 1 1 calc R U . . .
C7 C 0.44683(18) -0.16436(16) 0.30994(15) 0.0332(2) Uani 1 1 d . . . . .
C8 C 0.2463(2) -0.1246(2) 0.3143(3) 0.0697(6) Uani 1 1 d . . . . .
H8A H 0.1934 -0.0391 0.3717 0.105 Uiso 1 1 calc R U . . .
H8B H 0.1670 -0.2313 0.3671 0.105 Uiso 1 1 calc R U . . .
H8C H 0.2485 -0.0777 0.2070 0.105 Uiso 1 1 calc R U . . .
C9 C 0.5251(2) -0.2989(2) 0.21881(19) 0.0464(3) Uani 1 1 d . . . . .
H9A H 0.5268 -0.2504 0.1118 0.070 Uiso 1 1 calc R U . . .
H9B H 0.4434 -0.4041 0.2715 0.070 Uiso 1 1 calc R U . . .
H9C H 0.6547 -0.3275 0.2152 0.070 Uiso 1 1 calc R U . . .
C10 C 0.4475(3) -0.2453(2) 0.47545(17) 0.0539(4) Uani 1 1 d . . . . .
H10A H 0.3993 -0.1623 0.5362 0.081 Uiso 1 1 calc R U . . .
H10B H 0.5778 -0.2749 0.4695 0.081 Uiso 1 1 calc R U . . .
H10C H 0.3660 -0.3506 0.5267 0.081 Uiso 1 1 calc R 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 O1 1.9635(9) . ?
Cu1 O1 1.9635(9) 2_765 ?
Cu1 N1 2.0052(10) . ?
Cu1 N1 2.0052(10) 2_765 ?
O1 C1 1.2756(19) . ?
O2 C1 1.219(2) . ?
N1 C2 1.3344(15) . ?
N1 C6 1.3454(15) . ?
C2 C3 1.3817(17) . ?
C3 C4 1.3931(16) . ?
C4 C5 1.3950(16) . ?
C4 C7 1.5247(16) . ?
C5 C6 1.3800(17) . ?
C7 C8 1.514(2) . ?
C7 C10 1.529(2) . ?
C7 C9 1.5418(19) . ?

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 O1 180.0 . 2_765 ?
O1 Cu1 N1 90.22(4) . . ?
O1 Cu1 N1 89.78(4) 2_765 . ?
O1 Cu1 N1 89.78(4) . 2_765 ?
O1 Cu1 N1 90.22(4) 2_765 2_765 ?
N1 Cu1 N1 180.0 . 2_765 ?
C1 O1 Cu1 107.91(8) . . ?
C2 N1 C6 117.29(10) . . ?
C2 N1 Cu1 121.40(8) . . ?
C6 N1 Cu1 121.30(8) . . ?
O2 C1 O1 125.61(13) . . ?
N1 C2 C3 123.17(11) . . ?
C2 C3 C4 120.12(11) . . ?
C3 C4 C5 116.36(11) . . ?
C3 C4 C7 122.95(11) . . ?
C5 C4 C7 120.68(10) . . ?
C6 C5 C4 120.17(11) . . ?
N1 C6 C5 122.87(11) . . ?
C8 C7 C4 112.54(11) . . ?
C8 C7 C10 110.86(16) . . ?
C4 C7 C10 108.47(11) . . ?
C8 C7 C9 107.96(14) . . ?
C4 C7 C9 109.33(11) . . ?
C10 C7 C9 107.55(13) . . ?

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 O2 1.10(17) . . . . ?
C6 N1 C2 C3 1.15(18) . . . . ?
Cu1 N1 C2 C3 -179.19(9) . . . . ?
N1 C2 C3 C4 -0.84(18) . . . . ?
C2 C3 C4 C5 -0.38(17) . . . . ?
C2 C3 C4 C7 178.40(11) . . . . ?
C3 C4 C5 C6 1.23(18) . . . . ?
C7 C4 C5 C6 -177.57(11) . . . . ?
C2 N1 C6 C5 -0.24(19) . . . . ?
Cu1 N1 C6 C5 -179.90(10) . . . . ?
C4 C5 C6 N1 -1.0(2) . . . . ?
C3 C4 C7 C8 5.6(2) . . . . ?
C5 C4 C7 C8 -175.65(15) . . . . ?
C3 C4 C7 C10 -117.41(14) . . . . ?
C5 C4 C7 C10 61.32(16) . . . . ?
C3 C4 C7 C9 125.59(13) . . . . ?
C5 C4 C7 C9 -55.69(15) . . . . ?

_refine_diff_density_max         0.473
_refine_diff_density_min         -0.291
_refine_diff_density_rms         0.049

_shelxl_version_number           2013-4


_exptl_crystal_recrystallization_method 
'Re-crystallisation from solvent: acetonitrile'
_chemical_compound_source        acetonitrile
