# Electronic Supplementary Material (ESI) for CrystEngComm.
# 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_Cu-bcppm-H2O-acetone
_database_code_depnum_ccdc_archive 'CCDC 1451302'
_audit_update_record             
;
2016-02-02 deposited with the CCDC.
2016-02-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C30 H34 Cu N4 O8'
_chemical_formula_weight         642.15

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           orthorhombic
_symmetry_space_group_name_H-M   Pnma

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

_cell_length_a                   10.2536(2)
_cell_length_b                   19.8774(4)
_cell_length_c                   14.8763(7)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     3032.01(17)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    4840
_cell_measurement_theta_min      2.4596
_cell_measurement_theta_max      29.0053

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.08
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.407
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1340
_exptl_absorpt_coefficient_mu    0.776
_exptl_absorpt_correction_T_min  0.84318
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.7107
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   -9.00   92.00   1.0000  144.0000
omega____ theta____ kappa____ phi______ frames
    -       18.8463   37.0000  -30.0000 101

#__ type_ start__ end____ width___ exp.time_
  2 omega  -13.00   15.00   1.0000  144.0000
omega____ theta____ kappa____ phi______ frames
    -       18.8463  -37.0000 -180.0000 28

#__ type_ start__ end____ width___ exp.time_
  3 omega   71.00   96.00   1.0000  144.0000
omega____ theta____ kappa____ phi______ frames
    -       18.8463 -160.0000  -71.0000 25

#__ type_ start__ end____ width___ exp.time_
  4 omega   -9.00   92.00   1.0000  144.0000
omega____ theta____ kappa____ phi______ frames
    -       18.8463   37.0000 -150.0000 101

;
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.1695
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            14195
_diffrn_reflns_av_R_equivalents  0.0420
_diffrn_reflns_av_sigmaI/netI    0.0448
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       26
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_theta_min         2.62
_diffrn_reflns_theta_max         29.07
_reflns_number_total             3623
_reflns_number_gt                2888
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;

_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'X-Seed (Barbour, 2003)'
_computing_publication_material  'CIFTAB (Sheldrick)'

_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)+(0.0672P)²+2.8510P] 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         3623
_refine_ls_number_parameters     219
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0643
_refine_ls_R_factor_gt           0.0454
_refine_ls_wR_factor_ref         0.1320
_refine_ls_wR_factor_gt          0.1215
_refine_ls_goodness_of_fit_ref   1.051
_refine_ls_restrained_S_all      1.051
_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 0.68572(4) 0.2500 0.25668(3) 0.01308(14) Uani 1 2 d S . .
O29 O 0.77327(17) -0.17877(8) 0.67123(12) 0.0178(4) Uani 1 1 d . . .
O1 O 0.9037(3) 0.2500 0.2875(2) 0.0196(6) Uani 1 2 d S . .
O28 O 0.97466(19) -0.14590(11) 0.63369(17) 0.0393(6) Uani 1 1 d . . .
N11 N 0.6398(2) 0.17974(9) 0.34854(14) 0.0157(4) Uani 1 1 d . . .
N12 N 0.55867(18) 0.19038(10) 0.41961(14) 0.0157(4) Uani 1 1 d . . .
C15 C 0.7022(2) 0.12233(11) 0.36691(18) 0.0179(5) Uani 1 1 d . . .
H15 H 0.7665 0.1025 0.3293 0.021 Uiso 1 1 calc R . .
C1 C 0.4770(3) 0.2500 0.4203(3) 0.0166(7) Uani 1 2 d S . .
H1A H 0.4195 0.2500 0.3668 0.020 Uiso 1 2 calc SR . .
H1B H 0.4214 0.2500 0.4747 0.020 Uiso 1 2 calc SR . .
C25 C 0.6789(2) -0.05341(12) 0.60605(19) 0.0213(5) Uani 1 1 d . . .
H25 H 0.6288 -0.0732 0.6528 0.026 Uiso 1 1 calc R . .
C24 C 0.7973(2) -0.08241(12) 0.58048(19) 0.0213(5) Uani 1 1 d . . .
C14 C 0.6601(2) 0.09524(12) 0.44922(18) 0.0181(5) Uani 1 1 d . . .
C13 C 0.5680(2) 0.14108(12) 0.48090(18) 0.0186(5) Uani 1 1 d . . .
H13 H 0.5206 0.1380 0.5356 0.022 Uiso 1 1 calc R . .
C21 C 0.7046(2) 0.03310(12) 0.49308(19) 0.0208(5) Uani 1 1 d . . .
C26 C 0.6346(2) 0.00407(12) 0.56337(19) 0.0210(5) Uani 1 1 d . . .
H26 H 0.5550 0.0241 0.5823 0.025 Uiso 1 1 calc R . .
C27 C 0.8541(3) -0.14034(12) 0.63224(18) 0.0209(5) Uani 1 1 d . . .
C22 C 0.8201(3) 0.00201(14) 0.4650(2) 0.0318(7) Uani 1 1 d . . .
H22 H 0.8673 0.0197 0.4153 0.038 Uiso 1 1 calc R . .
C23 C 0.8657(3) -0.05451(14) 0.5095(2) 0.0314(7) Uani 1 1 d . . .
H23 H 0.9454 -0.0745 0.4909 0.038 Uiso 1 1 calc R . .
O43 O 0.3952(5) 0.1350(3) 0.6557(3) 0.1237(18) Uani 1 1 d . . .
C42 C 0.2297(9) 0.1411(7) 0.7640(5) 0.213(6) Uani 1 1 d . . .
H42A H 0.2155 0.1858 0.7380 0.319 Uiso 1 1 calc R . .
H42B H 0.2422 0.1453 0.8291 0.319 Uiso 1 1 calc R . .
H42C H 0.1537 0.1126 0.7519 0.319 Uiso 1 1 calc R . .
C40 C 0.3483(6) 0.1101(4) 0.7228(4) 0.0878(18) Uani 1 1 d . . .
C41 C 0.3986(11) 0.0487(4) 0.7658(5) 0.159(4) Uani 1 1 d . . .
H41A H 0.3374 0.0116 0.7557 0.238 Uiso 1 1 calc R . .
H41B H 0.4083 0.0564 0.8306 0.238 Uiso 1 1 calc R . .
H41C H 0.4836 0.0372 0.7399 0.238 Uiso 1 1 calc R . .
H7 H 0.922(3) 0.2783(18) 0.311(3) 0.050(13) Uiso 1 1 d . . .
C52 C 1.1183(6) 0.2500 0.5490(4) 0.0605(15) Uani 1 2 d S . .
H52A H 1.1381 0.2080 0.5806 0.091 Uiso 0.50 1 calc PR . .
H52B H 1.1825 0.2843 0.5658 0.091 Uiso 0.50 1 calc PR . .
H52C H 1.1220 0.2424 0.4840 0.091 Uiso 0.50 1 calc PR . .
C51 C 0.8708(7) 0.2500 0.5270(5) 0.078(2) Uani 1 2 d S . .
H51A H 0.8751 0.2010 0.5204 0.117 Uiso 0.50 1 calc PR . .
H51B H 0.8675 0.2710 0.4675 0.117 Uiso 0.50 1 calc PR . .
H51C H 0.7924 0.2621 0.5610 0.117 Uiso 0.50 1 calc PR . .
C50 C 0.9848(9) 0.2734(4) 0.5745(5) 0.062(2) Uani 0.50 1 d P . .
O53 O 0.9712(8) 0.3179(5) 0.6291(6) 0.134(4) Uani 0.50 1 d P . .


_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 O29 1.9486(16) 2_654 ?
Cu1 O29 1.9487(16) 7_765 ?
Cu1 N11 2.010(2) 8_565 ?
Cu1 N11 2.010(2) . ?
Cu1 O1 2.282(3) . ?
O29 C27 1.267(3) . ?
O29 Cu1 1.9486(16) 2_655 ?
O1 H7 0.69(3) . ?
O28 C27 1.242(3) . ?
N11 C15 1.337(3) . ?
N11 N12 1.362(3) . ?
N12 C13 1.342(3) . ?
N12 C1 1.451(3) . ?
C15 C14 1.405(3) . ?
C15 H15 0.9500 . ?
C1 N12 1.451(3) 8_565 ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C25 C26 1.384(3) . ?
C25 C24 1.397(4) . ?
C25 H25 0.9500 . ?
C24 C23 1.384(4) . ?
C24 C27 1.502(3) . ?
C14 C13 1.395(3) . ?
C14 C21 1.470(3) . ?
C13 H13 0.9500 . ?
C21 C26 1.394(4) . ?
C21 C22 1.400(4) . ?
C26 H26 0.9500 . ?
C22 C23 1.385(4) . ?
C22 H22 0.9500 . ?
C23 H23 0.9500 . ?
O43 C40 1.214(6) . ?
C42 C40 1.495(10) . ?
C42 H42A 0.9800 . ?
C42 H42B 0.9800 . ?
C42 H42C 0.9800 . ?
C40 C41 1.471(10) . ?
C41 H41A 0.9800 . ?
C41 H41B 0.9800 . ?
C41 H41C 0.9800 . ?
C52 C50 1.494(11) . ?
C52 H52A 0.9800 . ?
C52 H52B 0.9800 . ?
C52 H52C 0.9800 . ?
C51 C50 1.443(11) . ?
C51 H51A 0.9800 . ?
C51 H51B 0.9800 . ?
C51 H51C 0.9800 . ?
C50 O53 1.209(10) . ?

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
O29 Cu1 O29 93.20(10) 2_654 7_765 ?
O29 Cu1 N11 177.37(7) 2_654 8_565 ?
O29 Cu1 N11 89.38(8) 7_765 8_565 ?
O29 Cu1 N11 89.38(8) 2_654 . ?
O29 Cu1 N11 177.37(7) 7_765 . ?
N11 Cu1 N11 88.03(11) 8_565 . ?
O29 Cu1 O1 85.39(8) 2_654 . ?
O29 Cu1 O1 85.39(8) 7_765 . ?
N11 Cu1 O1 95.33(8) 8_565 . ?
N11 Cu1 O1 95.33(8) . . ?
C27 O29 Cu1 126.55(16) . 2_655 ?
Cu1 O1 H7 112(3) . . ?
C15 N11 N12 105.5(2) . . ?
C15 N11 Cu1 128.33(18) . . ?
N12 N11 Cu1 124.26(14) . . ?
C13 N12 N11 111.75(19) . . ?
C13 N12 C1 129.3(2) . . ?
N11 N12 C1 119.0(2) . . ?
N11 C15 C14 111.0(2) . . ?
N11 C15 H15 124.5 . . ?
C14 C15 H15 124.5 . . ?
N12 C1 N12 109.5(3) 8_565 . ?
N12 C1 H1A 109.8 8_565 . ?
N12 C1 H1A 109.8 . . ?
N12 C1 H1B 109.8 8_565 . ?
N12 C1 H1B 109.8 . . ?
H1A C1 H1B 108.2 . . ?
C26 C25 C24 120.1(2) . . ?
C26 C25 H25 120.0 . . ?
C24 C25 H25 120.0 . . ?
C23 C24 C25 118.9(2) . . ?
C23 C24 C27 120.1(2) . . ?
C25 C24 C27 120.9(2) . . ?
C13 C14 C15 104.6(2) . . ?
C13 C14 C21 127.5(2) . . ?
C15 C14 C21 127.8(2) . . ?
N12 C13 C14 107.2(2) . . ?
N12 C13 H13 126.4 . . ?
C14 C13 H13 126.4 . . ?
C26 C21 C22 118.5(2) . . ?
C26 C21 C14 121.4(2) . . ?
C22 C21 C14 120.1(2) . . ?
C25 C26 C21 121.1(2) . . ?
C25 C26 H26 119.4 . . ?
C21 C26 H26 119.4 . . ?
O28 C27 O29 126.1(2) . . ?
O28 C27 C24 117.6(2) . . ?
O29 C27 C24 116.3(2) . . ?
C23 C22 C21 120.0(3) . . ?
C23 C22 H22 120.0 . . ?
C21 C22 H22 120.0 . . ?
C24 C23 C22 121.3(3) . . ?
C24 C23 H23 119.4 . . ?
C22 C23 H23 119.4 . . ?
C40 C42 H42A 109.5 . . ?
C40 C42 H42B 109.5 . . ?
H42A C42 H42B 109.5 . . ?
C40 C42 H42C 109.5 . . ?
H42A C42 H42C 109.5 . . ?
H42B C42 H42C 109.5 . . ?
O43 C40 C41 123.8(7) . . ?
O43 C40 C42 119.5(7) . . ?
C41 C40 C42 116.7(6) . . ?
C40 C41 H41A 109.5 . . ?
C40 C41 H41B 109.5 . . ?
H41A C41 H41B 109.5 . . ?
C40 C41 H41C 109.5 . . ?
H41A C41 H41C 109.5 . . ?
H41B C41 H41C 109.5 . . ?
C50 C52 H52A 109.5 . . ?
C50 C52 H52B 109.5 . . ?
H52A C52 H52B 109.5 . . ?
C50 C52 H52C 109.5 . . ?
H52A C52 H52C 109.5 . . ?
H52B C52 H52C 109.5 . . ?
C50 C51 H51A 109.5 . . ?
C50 C51 H51B 109.5 . . ?
H51A C51 H51B 109.5 . . ?
C50 C51 H51C 109.5 . . ?
H51A C51 H51C 109.5 . . ?
H51B C51 H51C 109.5 . . ?
O53 C50 C51 118.1(9) . . ?
O53 C50 C52 120.3(8) . . ?
C51 C50 C52 121.2(6) . . ?

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
O29 Cu1 N11 C15 41.9(2) 2_654 . . . ?
O29 Cu1 N11 C15 -149.1(16) 7_765 . . . ?
N11 Cu1 N11 C15 -138.56(18) 8_565 . . . ?
O1 Cu1 N11 C15 -43.4(2) . . . . ?
O29 Cu1 N11 N12 -156.38(19) 2_654 . . . ?
O29 Cu1 N11 N12 12.6(18) 7_765 . . . ?
N11 Cu1 N11 N12 23.1(2) 8_565 . . . ?
O1 Cu1 N11 N12 118.32(18) . . . . ?
C15 N11 N12 C13 -0.6(3) . . . . ?
Cu1 N11 N12 C13 -165.79(16) . . . . ?
C15 N11 N12 C1 179.5(2) . . . . ?
Cu1 N11 N12 C1 14.3(3) . . . . ?
N12 N11 C15 C14 0.9(3) . . . . ?
Cu1 N11 C15 C14 165.26(17) . . . . ?
C13 N12 C1 N12 118.5(3) . . . 8_565 ?
N11 N12 C1 N12 -61.5(4) . . . 8_565 ?
C26 C25 C24 C23 -2.9(4) . . . . ?
C26 C25 C24 C27 173.5(2) . . . . ?
N11 C15 C14 C13 -0.8(3) . . . . ?
N11 C15 C14 C21 -179.9(2) . . . . ?
N11 N12 C13 C14 0.1(3) . . . . ?
C1 N12 C13 C14 -180.0(2) . . . . ?
C15 C14 C13 N12 0.4(3) . . . . ?
C21 C14 C13 N12 179.5(2) . . . . ?
C13 C14 C21 C26 16.2(4) . . . . ?
C15 C14 C21 C26 -164.9(3) . . . . ?
C13 C14 C21 C22 -163.3(3) . . . . ?
C15 C14 C21 C22 15.5(4) . . . . ?
C24 C25 C26 C21 1.6(4) . . . . ?
C22 C21 C26 C25 1.4(4) . . . . ?
C14 C21 C26 C25 -178.2(2) . . . . ?
Cu1 O29 C27 O28 8.6(4) 2_655 . . . ?
Cu1 O29 C27 C24 -170.74(17) 2_655 . . . ?
C23 C24 C27 O28 26.2(4) . . . . ?
C25 C24 C27 O28 -150.2(3) . . . . ?
C23 C24 C27 O29 -154.5(3) . . . . ?
C25 C24 C27 O29 29.2(4) . . . . ?
C26 C21 C22 C23 -3.0(5) . . . . ?
C14 C21 C22 C23 176.5(3) . . . . ?
C25 C24 C23 C22 1.3(5) . . . . ?
C27 C24 C23 C22 -175.1(3) . . . . ?
C21 C22 C23 C24 1.7(5) . . . . ?

_diffrn_measured_fraction_theta_max 0.870
_diffrn_reflns_theta_full        27.00
_diffrn_measured_fraction_theta_full 0.987
_refine_diff_density_max         0.758
_refine_diff_density_min         -0.444
_refine_diff_density_rms         0.086

###END
####################################################################### 
# 
# 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-bcppm-H2O-water
_database_code_depnum_ccdc_archive 'CCDC 1451303'
_audit_update_record             
;
2016-02-02 deposited with the CCDC.
2016-02-18 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C21 H16 Cu N4 O12'
_chemical_formula_weight         579.92

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           orthorhombic
_symmetry_space_group_name_H-M   Pnma

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

_cell_length_a                   9.4000(2)
_cell_length_b                   19.5102(3)
_cell_length_c                   14.7022(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     2696.32(8)
_cell_formula_units_Z            4
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    6774
_cell_measurement_theta_min      2.5006
_cell_measurement_theta_max      29.0667

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.46
_exptl_crystal_size_mid          0.29
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.429
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1180
_exptl_absorpt_coefficient_mu    0.875
_exptl_absorpt_correction_T_min  0.84409
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(2)
_diffrn_radiation_wavelength     0.7107
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_source         'Enhance (Mo) X-ray Source'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Xcalibur, Eos'
_diffrn_measurement_details      
;
#__ type_ start__ end____ width___ exp.time_
  1 omega   65.00   94.00   1.0000   57.5300
omega____ theta____ kappa____ phi______ frames
    -       18.8463  179.0000  -30.0000 29

#__ type_ start__ end____ width___ exp.time_
  2 omega  -74.00   46.00   1.0000   57.5300
omega____ theta____ kappa____ phi______ frames
    -      -19.6276    0.0000  -30.0000 120

#__ type_ start__ end____ width___ exp.time_
  3 omega  -13.00   51.00   1.0000   57.5300
omega____ theta____ kappa____ phi______ frames
    -       18.8463   77.0000 -180.0000 64

#__ type_ start__ end____ width___ exp.time_
  4 omega  -54.00   46.00   1.0000   57.5300
omega____ theta____ kappa____ phi______ frames
    -       18.8463  -37.0000   60.0000 100

;
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean 16.1695
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            15996
_diffrn_reflns_av_R_equivalents  0.0314
_diffrn_reflns_av_sigmaI/netI    0.0254
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -25
_diffrn_reflns_limit_k_max       24
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_theta_min         2.57
_diffrn_reflns_theta_max         29.13
_reflns_number_total             3341
_reflns_number_gt                2943
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_cell_refinement       
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_data_reduction        
;
CrysAlisPro, Agilent Technologies,
Version 1.171.35.11 (release 16-05-2011 CrysAlis171 .NET)
(compiled May 16 2011,17:55:39)
;
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'X-Seed (Barbour, 2003)'
_computing_publication_material  'CIFTAB (Sheldrick)'

_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)+(0.0449P)²+2.7276P] 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         3341
_refine_ls_number_parameters     180
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0427
_refine_ls_R_factor_gt           0.0354
_refine_ls_wR_factor_ref         0.0996
_refine_ls_wR_factor_gt          0.0954
_refine_ls_goodness_of_fit_ref   1.110
_refine_ls_restrained_S_all      1.110
_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 0.88348(3) 0.2500 0.736225(19) 0.01042(11) Uani 1 2 d S . .
O1 O 0.6326(2) 0.2500 0.70881(13) 0.0152(4) Uani 1 2 d SD . .
O28 O 0.47822(17) -0.15218(9) 0.39796(12) 0.0330(4) Uani 1 1 d . . .
O29 O 0.67518(15) -0.17578(6) 0.31860(8) 0.0151(3) Uani 1 1 d . . .
N12 N 0.92060(18) 0.17760(8) 0.64109(10) 0.0131(3) Uani 1 1 d . . .
N11 N 0.99517(17) 0.18940(7) 0.56369(10) 0.0125(3) Uani 1 1 d . . .
C27 C 0.6045(2) -0.14151(10) 0.37557(12) 0.0159(4) Uani 1 1 d . . .
C14 C 0.8732(2) 0.09485(10) 0.53814(12) 0.0154(4) Uani 1 1 d . . .
C1 C 1.0841(3) 0.2500 0.55859(17) 0.0130(5) Uani 1 2 d S . .
H1A H 1.1379 0.2500 0.5007 0.016 Uiso 1 2 calc SR . .
H1B H 1.1532 0.2500 0.6094 0.016 Uiso 1 2 calc SR . .
C22 C 0.8556(2) 0.00836(10) 0.41325(12) 0.0179(4) Uani 1 1 d . . .
H22 H 0.9303 0.0311 0.3818 0.021 Uiso 1 1 calc R . .
C15 C 0.9690(2) 0.14074(9) 0.50080(12) 0.0147(4) Uani 1 1 d . . .
H15 H 1.0091 0.1384 0.4416 0.018 Uiso 1 1 calc R . .
C23 C 0.7927(2) -0.04930(10) 0.37520(12) 0.0175(4) Uani 1 1 d . . .
H23 H 0.8267 -0.0665 0.3188 0.021 Uiso 1 1 calc R . .
C13 C 0.8468(2) 0.12071(9) 0.62595(12) 0.0147(4) Uani 1 1 d . . .
H13 H 0.7844 0.1001 0.6688 0.018 Uiso 1 1 calc R . .
C21 C 0.8098(2) 0.03319(10) 0.49734(13) 0.0170(4) Uani 1 1 d . . .
C24 C 0.6811(2) -0.08204(10) 0.41863(12) 0.0170(4) Uani 1 1 d . . .
C26 C 0.7012(3) -0.00160(12) 0.54217(15) 0.0320(6) Uani 1 1 d . . .
H26 H 0.6707 0.0140 0.6002 0.038 Uiso 1 1 calc R . .
C25 C 0.63716(16) -0.05824(8) 0.50407(9) 0.0311(6) Uani 1 1 d . . .
H25 H 0.5631 -0.0812 0.5358 0.037 Uiso 1 1 calc R . .
O3 O 0.81709(16) 0.25000(8) 0.10609(9) 0.0484(7) Uani 1 2 d SR . .
O2 O 0.31450(16) 0.14307(8) 0.26550(9) 0.0478(5) Uani 1 1 d R . .
O4 O 1.0943(4) 0.2500 0.02755(19) 0.0530(8) Uani 1 2 d S . .
O5 O 0.5702(3) 0.06876(13) 0.27220(16) 0.0596(6) Uani 1 1 d . . .
O6 O 0.3357(3) 0.2500 0.14048(18) 0.0462(7) Uani 1 2 d S . .
H1 H 0.612(3) 0.2830(10) 0.6785(16) 0.030(7) Uiso 1 1 d D . .


_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 O29 1.9666(12) 2_655 ?
Cu1 O29 1.9667(12) 7_766 ?
Cu1 N12 2.0181(15) 8_565 ?
Cu1 N12 2.0182(15) . ?
Cu1 O1 2.393(2) . ?
O1 H1 0.807(16) . ?
O28 C27 1.249(3) . ?
O29 C27 1.261(2) . ?
O29 Cu1 1.9667(12) 2_654 ?
N12 C13 1.328(2) . ?
N12 N11 1.356(2) . ?
N11 C15 1.348(2) . ?
N11 C1 1.450(2) . ?
C27 C24 1.505(3) . ?
C14 C15 1.384(3) . ?
C14 C13 1.408(2) . ?
C14 C21 1.470(3) . ?
C1 N11 1.450(2) 8_565 ?
C1 H1A 0.9900 . ?
C1 H1B 0.9900 . ?
C22 C23 1.389(3) . ?
C22 C21 1.396(3) . ?
C22 H22 0.9500 . ?
C15 H15 0.9500 . ?
C23 C24 1.385(3) . ?
C23 H23 0.9500 . ?
C13 H13 0.9500 . ?
C21 C26 1.392(3) . ?
C24 C25 1.401(2) . ?
C26 C25 1.378(3) . ?
C26 H26 0.9500 . ?
C25 H25 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
O29 Cu1 O29 94.84(8) 2_655 7_766 ?
O29 Cu1 N12 172.13(6) 2_655 8_565 ?
O29 Cu1 N12 87.70(6) 7_766 8_565 ?
O29 Cu1 N12 87.70(6) 2_655 . ?
O29 Cu1 N12 172.13(6) 7_766 . ?
N12 Cu1 N12 88.83(8) 8_565 . ?
O29 Cu1 O1 80.06(5) 2_655 . ?
O29 Cu1 O1 80.06(5) 7_766 . ?
N12 Cu1 O1 93.08(6) 8_565 . ?
N12 Cu1 O1 93.08(6) . . ?
Cu1 O1 H1 109.2(19) . . ?
C27 O29 Cu1 130.66(13) . 2_654 ?
C13 N12 N11 105.73(14) . . ?
C13 N12 Cu1 127.67(13) . . ?
N11 N12 Cu1 123.51(11) . . ?
C15 N11 N12 111.20(15) . . ?
C15 N11 C1 130.11(17) . . ?
N12 N11 C1 118.66(15) . . ?
O28 C27 O29 125.98(18) . . ?
O28 C27 C24 118.17(17) . . ?
O29 C27 C24 115.85(17) . . ?
C15 C14 C13 104.26(16) . . ?
C15 C14 C21 129.15(17) . . ?
C13 C14 C21 126.59(18) . . ?
N11 C1 N11 109.3(2) . 8_565 ?
N11 C1 H1A 109.8 . . ?
N11 C1 H1A 109.8 8_565 . ?
N11 C1 H1B 109.8 . . ?
N11 C1 H1B 109.8 8_565 . ?
H1A C1 H1B 108.3 . . ?
C23 C22 C21 120.45(19) . . ?
C23 C22 H22 119.8 . . ?
C21 C22 H22 119.8 . . ?
N11 C15 C14 107.61(16) . . ?
N11 C15 H15 126.2 . . ?
C14 C15 H15 126.2 . . ?
C24 C23 C22 120.71(17) . . ?
C24 C23 H23 119.6 . . ?
C22 C23 H23 119.6 . . ?
N12 C13 C14 111.20(17) . . ?
N12 C13 H13 124.4 . . ?
C14 C13 H13 124.4 . . ?
C26 C21 C22 118.45(18) . . ?
C26 C21 C14 120.19(17) . . ?
C22 C21 C14 121.36(18) . . ?
C23 C24 C25 118.92(17) . . ?
C23 C24 C27 121.62(16) . . ?
C25 C24 C27 119.45(17) . . ?
C25 C26 C21 121.28(18) . . ?
C25 C26 H26 119.4 . . ?
C21 C26 H26 119.4 . . ?
C26 C25 C24 120.11(16) . . ?
C26 C25 H25 119.9 . . ?
C24 C25 H25 119.9 . . ?

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
O29 Cu1 N12 C13 36.69(16) 2_655 . . . ?
O29 Cu1 N12 C13 -72.4(5) 7_766 . . . ?
N12 Cu1 N12 C13 -136.24(14) 8_565 . . . ?
O1 Cu1 N12 C13 -43.22(16) . . . . ?
O29 Cu1 N12 N11 -166.10(15) 2_655 . . . ?
O29 Cu1 N12 N11 84.9(5) 7_766 . . . ?
N12 Cu1 N12 N11 20.96(18) 8_565 . . . ?
O1 Cu1 N12 N11 113.99(14) . . . . ?
C13 N12 N11 C15 -0.1(2) . . . . ?
Cu1 N12 N11 C15 -161.49(13) . . . . ?
C13 N12 N11 C1 178.29(17) . . . . ?
Cu1 N12 N11 C1 16.9(2) . . . . ?
Cu1 O29 C27 O28 6.7(3) 2_654 . . . ?
Cu1 O29 C27 C24 -172.40(12) 2_654 . . . ?
C15 N11 C1 N11 113.9(2) . . . 8_565 ?
N12 N11 C1 N11 -64.1(2) . . . 8_565 ?
N12 N11 C15 C14 0.0(2) . . . . ?
C1 N11 C15 C14 -178.11(19) . . . . ?
C13 C14 C15 N11 0.1(2) . . . . ?
C21 C14 C15 N11 179.45(19) . . . . ?
C21 C22 C23 C24 1.8(3) . . . . ?
N11 N12 C13 C14 0.1(2) . . . . ?
Cu1 N12 C13 C14 160.50(13) . . . . ?
C15 C14 C13 N12 -0.1(2) . . . . ?
C21 C14 C13 N12 -179.51(18) . . . . ?
C23 C22 C21 C26 0.7(3) . . . . ?
C23 C22 C21 C14 -178.91(19) . . . . ?
C15 C14 C21 C26 -171.8(2) . . . . ?
C13 C14 C21 C26 7.5(3) . . . . ?
C15 C14 C21 C22 7.8(3) . . . . ?
C13 C14 C21 C22 -172.96(19) . . . . ?
C22 C23 C24 C25 -3.3(3) . . . . ?
C22 C23 C24 C27 175.57(18) . . . . ?
O28 C27 C24 C23 -153.4(2) . . . . ?
O29 C27 C24 C23 25.8(3) . . . . ?
O28 C27 C24 C25 25.5(3) . . . . ?
O29 C27 C24 C25 -155.28(17) . . . . ?
C22 C21 C26 C25 -1.6(4) . . . . ?
C14 C21 C26 C25 178.0(2) . . . . ?
C21 C26 C25 C24 0.1(3) . . . . ?
C23 C24 C25 C26 2.4(3) . . . . ?
C27 C24 C25 C26 -176.6(2) . . . . ?

_diffrn_measured_fraction_theta_max 0.896
_diffrn_reflns_theta_full        27.00
_diffrn_measured_fraction_theta_full 0.992
_refine_diff_density_max         0.532
_refine_diff_density_min         -0.330
_refine_diff_density_rms         0.079

###END
