# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2014

#######################################################################
#
#                 Cambridge Crystallographic Data Centre
#                                CCDC 
# 
#######################################################################
# 
#  This CIF contains data from an original supplementary publication
#  deposited with the CCDC, and may include chemical, crystal,
#  experimental, refinement, atomic coordinates,
#  anisotropic displacement parameters and molecular geometry data,
#  as required by the journal to which it was submitted.
#
#  This CIF is provided on the understanding that it is used for bona
#  fide research purposes only. It may contain copyright material
#  of the CCDC or of third parties, and may not be copied or further
#  disseminated in any form, whether machine-readable or not,
#  except for the purpose of generating routine backup copies
#  on your local computer system.
# 
#  For further information on the CCDC, data deposition and
#  data retrieval see:
#                         www.ccdc.cam.ac.uk
#
#  Bona fide researchers may freely download Mercury and enCIFer
#  from this site to visualise CIF-encoded structures and 
#  to carry out CIF format checking respectively.
#
data_Cu

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C28 H40 Cu N5 O7'
_chemical_formula_weight         622.19

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           tetragonal
_symmetry_space_group_name_H-M   'P 4/n'

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y+1/2, x, z'
'-x+1/2, -y+1/2, z'
'y, -x+1/2, z'
'-x, -y, -z'
'y-1/2, -x, -z'
'x-1/2, y-1/2, -z'
'-y, x-1/2, -z'

_cell_length_a                   16.417(2)
_cell_length_b                   16.417(2)
_cell_length_c                   6.598(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1778.3(6)
_cell_formula_units_Z            2
_cell_measurement_temperature    298(2)
_cell_measurement_reflns_used    1402
_cell_measurement_theta_min      2.96
_cell_measurement_theta_max      20.01

_exptl_crystal_description       block
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_size_max          0.26
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.162
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             656
_exptl_absorpt_coefficient_mu    0.658
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8280
_exptl_absorpt_correction_T_max  0.8961
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      298(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 SMART II'
_diffrn_measurement_method       ?
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         0
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            10804
_diffrn_reflns_av_R_equivalents  0.0519
_diffrn_reflns_av_sigmaI/netI    0.0467
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       21
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_l_min       -8
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         3.09
_diffrn_reflns_theta_max         28.45
_reflns_number_total             2227
_reflns_number_gt                1113
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_cell_refinement       APEX2
_computing_data_reduction        APEX2
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    APEX2
_computing_publication_material  APEX2

_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)+(0.0000P)²+1.2000P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2227
_refine_ls_number_parameters     168
_refine_ls_number_restraints     199
_refine_ls_R_factor_all          0.1116
_refine_ls_R_factor_gt           0.0482
_refine_ls_wR_factor_ref         0.0987
_refine_ls_wR_factor_gt          0.0823
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_restrained_S_all      0.989
_refine_ls_shift/su_max          0.000
_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 0.2500 0.7500 0.5000 0.0708(2) Uani 1 4 d S . .
N1 N 0.17140(13) 0.68652(13) 0.3194(3) 0.0712(6) Uani 1 1 d . . .
C1 C 0.19755(19) 0.62857(19) 0.1948(5) 0.0900(9) Uani 1 1 d . . .
H1 H 0.2534 0.6205 0.1839 0.108 Uiso 1 1 calc R . .
C2 C 0.1471(2) 0.5798(2) 0.0807(5) 0.1025(11) Uani 1 1 d . . .
H2 H 0.1690 0.5393 -0.0016 0.123 Uiso 1 1 calc R . .
C3 C 0.0643(2) 0.5911(2) 0.0891(5) 0.0935(10) Uani 1 1 d . . .
C4 C 0.03691(19) 0.6507(2) 0.2151(5) 0.0954(10) Uani 1 1 d . . .
H4 H -0.0187 0.6603 0.2268 0.114 Uiso 1 1 calc R . .
C5 C 0.09081(18) 0.69683(17) 0.3250(5) 0.0804(8) Uani 1 1 d . . .
H5 H 0.0700 0.7376 0.4081 0.096 Uiso 1 1 calc R . .
C6 C -0.0034(10) 0.5432(8) -0.026(3) 0.089(3) Uani 0.67(3) 1 d PU . 1
H6 H -0.0577 0.5642 0.0075 0.106 Uiso 0.67(3) 1 calc PR . 1
C7 C 0.0179(14) 0.5583(12) -0.258(2) 0.149(6) Uani 0.67(3) 1 d PU . 1
H7A H 0.0718 0.5386 -0.2853 0.224 Uiso 0.67(3) 1 calc PR . 1
H7B H 0.0152 0.6156 -0.2864 0.224 Uiso 0.67(3) 1 calc PR . 1
H7C H -0.0206 0.5299 -0.3414 0.224 Uiso 0.67(3) 1 calc PR . 1
C6B C 0.025(2) 0.531(2) -0.070(4) 0.095(6) Uani 0.33(3) 1 d PU . 2
H6B H 0.0693 0.5003 -0.1347 0.114 Uiso 0.33(3) 1 calc PR . 2
C7B C -0.021(2) 0.570(2) -0.225(6) 0.130(8) Uani 0.33(3) 1 d PU . 2
H7D H -0.0452 0.5302 -0.3117 0.195 Uiso 0.33(3) 1 calc PR . 2
H7E H 0.0148 0.6044 -0.3043 0.195 Uiso 0.33(3) 1 calc PR . 2
H7F H -0.0626 0.6033 -0.1650 0.195 Uiso 0.33(3) 1 calc PR . 2
N2 N -0.2442(12) 0.6218(8) 0.517(5) 0.408(10) Uani 0.25 1 d PDU A 1
O1 O -0.190(2) 0.612(2) 0.394(6) 0.405(10) Uani 0.25 1 d PDU A 1
O2 O -0.2390(15) 0.5938(15) 0.687(5) 0.420(12) Uani 0.25 1 d PDU A 1
O3 O -0.3055(13) 0.6606(12) 0.469(5) 0.423(10) Uani 0.25 1 d PDU A 1
O4 O -0.1963(18) 0.636(2) 0.208(8) 0.407(10) Uani 0.25 1 d PU B 2
O5 O -0.179(2) 0.5795(17) 0.413(8) 0.394(11) Uani 0.25 1 d PU B 2
O6 O -0.2572(17) 0.6457(18) -0.032(9) 0.413(11) Uani 0.25 1 d PU B 2
O7 O -0.2070(19) 0.644(2) -0.010(9) 0.405(10) Uani 0.25 1 d PU B 2

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
Cu1 0.0642(3) 0.0642(3) 0.0838(5) 0.000 0.000 0.000
N1 0.0651(14) 0.0718(15) 0.0768(16) -0.0023(13) 0.0018(13) -0.0079(12)
C1 0.077(2) 0.099(2) 0.094(2) -0.021(2) 0.0104(18) -0.0098(18)
C2 0.110(3) 0.100(2) 0.098(3) -0.030(2) 0.010(2) -0.024(2)
C3 0.105(3) 0.095(2) 0.080(2) 0.0065(19) -0.011(2) -0.041(2)
C4 0.073(2) 0.108(3) 0.105(3) -0.001(2) -0.0114(19) -0.0202(19)
C5 0.0717(19) 0.0799(19) 0.090(2) -0.0030(17) -0.0046(17) -0.0047(16)
C6 0.091(6) 0.099(4) 0.076(7) 0.004(5) 0.007(5) -0.025(5)
C7 0.192(13) 0.186(11) 0.070(5) 0.026(6) -0.031(8) -0.111(11)
C6B 0.098(13) 0.118(12) 0.069(11) -0.004(9) 0.019(9) -0.061(10)
C7B 0.157(19) 0.126(12) 0.108(15) 0.046(10) -0.033(13) -0.067(14)
N2 0.180(12) 0.206(12) 0.84(3) -0.020(17) -0.066(18) 0.031(11)
O1 0.173(11) 0.200(12) 0.84(3) -0.021(17) -0.059(17) 0.029(11)
O2 0.221(15) 0.196(15) 0.84(3) 0.02(2) -0.06(2) 0.032(13)
O3 0.205(11) 0.212(11) 0.85(3) -0.030(16) -0.058(17) 0.009(10)
O4 0.170(11) 0.208(11) 0.84(3) -0.028(17) -0.048(17) 0.026(10)
O5 0.166(13) 0.193(15) 0.82(3) -0.027(18) -0.068(17) 0.010(13)
O6 0.209(16) 0.188(12) 0.84(3) -0.018(19) -0.04(2) -0.042(14)
O7 0.165(11) 0.207(11) 0.84(3) -0.026(17) -0.062(18) 0.041(10)

_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 N1 2.042(2) . ?
Cu1 N1 2.042(2) 6_566 ?
Cu1 N1 2.042(2) 8_666 ?
Cu1 N1 2.042(2) 3_565 ?
N1 C1 1.329(3) . ?
N1 C5 1.334(3) . ?
C1 C2 1.376(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.374(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.359(4) . ?
C3 C6 1.559(14) . ?
C3 C6B 1.58(3) . ?
C4 C5 1.372(4) . ?
C4 H4 0.9300 . ?
C5 H5 0.9300 . ?
C6 C6 1.46(3) 5_565 ?
C6 C7 1.59(3) . ?
C6 H6 0.9800 . ?
C7 H7A 0.9600 . ?
C7 H7B 0.9600 . ?
C7 H7C 0.9600 . ?
C6B C7B 1.43(5) . ?
C6B C6B 1.60(4) 5_565 ?
C6B H6B 0.9800 . ?
C7B H7D 0.9600 . ?
C7B H7E 0.9600 . ?
C7B H7F 0.9600 . ?
N2 O2 1.218(10) . ?
N2 O1 1.219(10) . ?
N2 O3 1.232(10) . ?
N2 O3 1.85(2) 2_565 ?
O1 O3 1.52(4) 2_565 ?
O3 O1 1.52(4) 4_455 ?
O3 N2 1.85(2) 4_455 ?
O4 O7 1.45(7) . ?
O4 O5 1.66(6) . ?
O6 O7 0.84(3) . ?

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
N1 Cu1 N1 109.90(6) . 6_566 ?
N1 Cu1 N1 109.90(6) . 8_666 ?
N1 Cu1 N1 108.62(12) 6_566 8_666 ?
N1 Cu1 N1 108.62(13) . 3_565 ?
N1 Cu1 N1 109.90(6) 6_566 3_565 ?
N1 Cu1 N1 109.90(6) 8_666 3_565 ?
C1 N1 C5 115.3(3) . . ?
C1 N1 Cu1 121.5(2) . . ?
C5 N1 Cu1 123.1(2) . . ?
N1 C1 C2 124.1(3) . . ?
N1 C1 H1 117.9 . . ?
C2 C1 H1 117.9 . . ?
C3 C2 C1 119.6(3) . . ?
C3 C2 H2 120.2 . . ?
C1 C2 H2 120.2 . . ?
C4 C3 C2 116.7(3) . . ?
C4 C3 C6 115.2(7) . . ?
C2 C3 C6 128.1(7) . . ?
C4 C3 C6B 136.3(16) . . ?
C2 C3 C6B 106.9(16) . . ?
C6 C3 C6B 21.6(11) . . ?
C3 C4 C5 120.5(3) . . ?
C3 C4 H4 119.8 . . ?
C5 C4 H4 119.8 . . ?
N1 C5 C4 123.7(3) . . ?
N1 C5 H5 118.1 . . ?
C4 C5 H5 118.1 . . ?
C6 C6 C3 108.8(13) 5_565 . ?
C6 C6 C7 111(2) 5_565 . ?
C3 C6 C7 103.4(14) . . ?
C6 C6 H6 111.1 5_565 . ?
C3 C6 H6 111.1 . . ?
C7 C6 H6 111.1 . . ?
C7B C6B C3 114(3) . . ?
C7B C6B C6B 116(4) . 5_565 ?
C3 C6B C6B 103(3) . 5_565 ?
C7B C6B H6B 108.0 . . ?
C3 C6B H6B 108.0 . . ?
C6B C6B H6B 108.0 5_565 . ?
C6B C7B H7D 109.5 . . ?
C6B C7B H7E 109.5 . . ?
H7D C7B H7E 109.5 . . ?
C6B C7B H7F 109.5 . . ?
H7D C7B H7F 109.5 . . ?
H7E C7B H7F 109.5 . . ?
O2 N2 O1 120.5(9) . . ?
O2 N2 O3 119.4(9) . . ?
O1 N2 O3 120.1(9) . . ?
O2 N2 O3 110(2) . 2_565 ?
O1 N2 O3 55.1(19) . 2_565 ?
O3 N2 O3 103.2(16) . 2_565 ?
N2 O1 O3 83.9(18) . 2_565 ?
N2 O3 O1 166.9(17) . 4_455 ?
N2 O3 N2 150.2(19) . 4_455 ?
O1 O3 N2 41.0(6) 4_455 4_455 ?
O7 O4 O5 152(4) . . ?
O6 O7 O4 107(8) . . ?

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
N1 Cu1 N1 C1 -176.7(2) 6_566 . . . ?
N1 Cu1 N1 C1 -57.25(19) 8_666 . . . ?
N1 Cu1 N1 C1 63.0(2) 3_565 . . . ?
N1 Cu1 N1 C5 -0.3(2) 6_566 . . . ?
N1 Cu1 N1 C5 119.2(3) 8_666 . . . ?
N1 Cu1 N1 C5 -120.5(2) 3_565 . . . ?
C5 N1 C1 C2 -1.7(5) . . . . ?
Cu1 N1 C1 C2 175.0(3) . . . . ?
N1 C1 C2 C3 1.5(5) . . . . ?
C1 C2 C3 C4 -0.9(5) . . . . ?
C1 C2 C3 C6 -179.8(7) . . . . ?
C1 C2 C3 C6B 175.7(11) . . . . ?
C2 C3 C4 C5 0.6(5) . . . . ?
C6 C3 C4 C5 179.7(6) . . . . ?
C6B C3 C4 C5 -174.7(14) . . . . ?
C1 N1 C5 C4 1.4(4) . . . . ?
Cu1 N1 C5 C4 -175.3(2) . . . . ?
C3 C4 C5 N1 -0.9(5) . . . . ?
C4 C3 C6 C6 -121.2(17) . . . 5_565 ?
C2 C3 C6 C6 58(2) . . . 5_565 ?
C6B C3 C6 C6 69(4) . . . 5_565 ?
C4 C3 C6 C7 120.7(15) . . . . ?
C2 C3 C6 C7 -60.3(15) . . . . ?
C6B C3 C6 C7 -49(4) . . . . ?
C4 C3 C6B C7B 56(4) . . . . ?
C2 C3 C6B C7B -120(4) . . . . ?
C6 C3 C6B C7B 70(6) . . . . ?
C4 C3 C6B C6B -70(4) . . . 5_565 ?
C2 C3 C6B C6B 114(4) . . . 5_565 ?
C6 C3 C6B C6B -56(3) . . . 5_565 ?
O2 N2 O1 O3 -95(2) . . . 2_565 ?
O3 N2 O1 O3 85(2) . . . 2_565 ?
O2 N2 O3 O1 -90(14) . . . 4_455 ?
O1 N2 O3 O1 90(14) . . . 4_455 ?
O3 N2 O3 O1 147(12) 2_565 . . 4_455 ?
O2 N2 O3 N2 53(3) . . . 4_455 ?
O1 N2 O3 N2 -127(3) . . . 4_455 ?
O3 N2 O3 N2 -70(4) 2_565 . . 4_455 ?
O5 O4 O7 O6 99(8) . . . . ?

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        28.45
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.212
_refine_diff_density_min         -0.164
_refine_diff_density_rms         0.036
_database_code_depnum_ccdc_archive 'CCDC 972847'
