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

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_p
_database_code_depnum_ccdc_archive 'CCDC 1049754'
_audit_update_record             
;
2015-05-11 deposited with the CCDC.
2015-05-29 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
; 
 ? 
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C17 H11 Cu N3 O5'
_chemical_formula_weight         400.83

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'

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   'Pccn '

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

_cell_length_a                   16.269(2)
_cell_length_b                   20.730(3)
_cell_length_c                   14.9828(19)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     5053.2(11)
_cell_formula_units_Z            8
_cell_measurement_temperature    150(2)
_cell_measurement_reflns_used    4469
_cell_measurement_theta_min      2.50
_cell_measurement_theta_max      26.68

_exptl_crystal_description       block
_exptl_crystal_colour            blue
_exptl_crystal_size_max          0.18
_exptl_crystal_size_mid          0.18
_exptl_crystal_size_min          0.16
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.054
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1624
_exptl_absorpt_coefficient_mu    0.887
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.8566
_exptl_absorpt_correction_T_max  0.8711
_exptl_absorpt_process_details   sadabs

_exptl_special_details           
; 
 ? 
;

_diffrn_ambient_temperature      150(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  'CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            28595
_diffrn_reflns_av_R_equivalents  0.0639
_diffrn_reflns_av_sigmaI/netI    0.0558
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_theta_min         1.96
_diffrn_reflns_theta_max         27.45
_reflns_number_total             5743
_reflns_number_gt                4052
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Bruker SMART'
_computing_cell_refinement       'Bruker SMART'
_computing_data_reduction        'Bruker SAINT'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'

_refine_special_details          
; 
 Refinement of F² against ALL reflections.  The weighted R-factor wR and 
 goodness of fit S are based on F², conventional R-factors R are based 
 on F, with F set to zero for negative F². The threshold expression of 
 F² > 2sigma(F²) is used only for calculating R-factors(gt) etc. and is 
 not relevant to the choice of reflections for refinement.  R-factors based 
 on F² are statistically about twice as large as those based on F, and R- 
 factors based on ALL data will be even larger. 
;

# SQUEEZE RESULTS (APPEND TO CIF) 
# Note: Data are Listed for all Voids in the P1 Unit Cell 
# i.e. Centre of Gravity, Solvent Accessible Volume, 
# Recovered number of Electrons in the Void and 
# Details about the Squeezed Material 
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 -0.026 0.422 0.000 1152 390 ' '
2 0.743 0.744 0.500 1152 389 ' '
_platon_squeeze_details          
; 
;

_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)+(0.0625P)²+0.0000P] 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         5743
_refine_ls_number_parameters     235
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0738
_refine_ls_R_factor_gt           0.0471
_refine_ls_wR_factor_ref         0.1189
_refine_ls_wR_factor_gt          0.1120
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_restrained_S_all      1.031
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C10 C 0.21676(17) 0.43159(13) 0.85965(18) 0.0211(6) Uani 1 1 d . . .
C15 C 0.01301(18) 0.25237(14) 0.82923(18) 0.0231(6) Uani 1 1 d . . .
C1 C 0.00873(16) 0.43887(13) 0.61480(17) 0.0166(5) Uani 1 1 d . . .
Cu1 Cu 0.106188(19) 0.566301(15) 0.53314(2) 0.01530(10) Uani 1 1 d . . .
O3 O 0.19429(11) 0.55828(9) 0.62815(12) 0.0209(4) Uani 1 1 d . . .
C3 C 0.11238(17) 0.43109(13) 0.73708(18) 0.0203(6) Uani 1 1 d . . .
H3A H 0.1332 0.4716 0.7177 0.024 Uiso 1 1 calc R . .
N1 N 0.33118(13) 0.50331(11) 0.95802(14) 0.0182(5) Uani 1 1 d . . .
O1 O 0.02698(11) 0.49602(9) 0.60255(12) 0.0217(4) Uani 1 1 d . . .
O4 O 0.26310(14) 0.61874(11) 0.53551(15) 0.0395(6) Uani 1 1 d . . .
O2 O -0.04069(10) 0.40514(9) 0.56823(12) 0.0176(4) Uani 1 1 d . . .
N2 N -0.05753(14) 0.14097(11) 0.90019(15) 0.0209(5) Uani 1 1 d . . .
C5 C 0.11790(17) 0.34013(13) 0.83717(19) 0.0235(6) Uani 1 1 d . . .
H5A H 0.1436 0.3176 0.8849 0.028 Uiso 1 1 calc R . .
C2 C 0.04588(16) 0.40358(13) 0.69346(17) 0.0178(6) Uani 1 1 d . . .
O5 O 0.32303(14) 0.58043(14) 0.65321(18) 0.0588(8) Uani 1 1 d . . .
N3 N 0.26223(15) 0.58654(13) 0.60546(17) 0.0292(6) Uani 1 1 d . . .
C11 C 0.26342(16) 0.47995(14) 0.81973(19) 0.0239(6) Uani 1 1 d . . .
H11A H 0.2579 0.4886 0.7578 0.029 Uiso 1 1 calc R . .
C13 C -0.10347(19) 0.18997(16) 0.8723(2) 0.0385(9) Uani 1 1 d . . .
H13A H -0.1615 0.1865 0.8773 0.046 Uiso 1 1 calc R . .
C8 C 0.28958(18) 0.45400(14) 0.99439(19) 0.0228(6) Uani 1 1 d . . .
H8A H 0.3003 0.4433 1.0549 0.027 Uiso 1 1 calc R . .
C9 C 0.23233(18) 0.41806(14) 0.94887(19) 0.0238(7) Uani 1 1 d . . .
H9A H 0.2036 0.3842 0.9782 0.029 Uiso 1 1 calc R . .
C16 C 0.06093(17) 0.20081(14) 0.85807(18) 0.0238(6) Uani 1 1 d . . .
H16A H 0.1191 0.2031 0.8542 0.029 Uiso 1 1 calc R . .
C4 C 0.14918(17) 0.39956(13) 0.80973(18) 0.0202(6) Uani 1 1 d . . .
C12 C 0.31767(17) 0.51508(14) 0.87108(18) 0.0240(6) Uani 1 1 d . . .
H12A H 0.3470 0.5494 0.8436 0.029 Uiso 1 1 calc R . .
C14 C -0.07090(19) 0.24571(16) 0.8365(2) 0.0402(9) Uani 1 1 d . . .
H14A H -0.1062 0.2793 0.8170 0.048 Uiso 1 1 calc R . .
C17 C 0.02392(18) 0.14682(14) 0.89202(19) 0.0244(6) Uani 1 1 d . . .
H17A H 0.0577 0.1119 0.9106 0.029 Uiso 1 1 calc R . .
C6 C 0.04894(17) 0.31327(14) 0.79505(19) 0.0237(6) Uani 1 1 d . . .
C7 C 0.01383(17) 0.34546(13) 0.72235(18) 0.0228(6) Uani 1 1 d . . .
H7A H -0.0323 0.3273 0.6927 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
C10 C9 1.389(4) . ?
C10 C11 1.392(4) . ?
C10 C4 1.486(4) . ?
C15 C14 1.376(4) . ?
C15 C16 1.392(4) . ?
C15 C6 1.482(4) . ?
C1 O1 1.235(3) . ?
C1 O2 1.274(3) . ?
C1 C2 1.513(3) . ?
Cu1 O2 1.9477(17) 5_566 ?
Cu1 N1 2.003(2) 8_655 ?
Cu1 N2 2.005(2) 3_556 ?
Cu1 O3 2.0270(18) . ?
Cu1 O1 2.2056(19) . ?
O3 N3 1.296(3) . ?
C3 C2 1.387(4) . ?
C3 C4 1.404(4) . ?
N1 C8 1.342(3) . ?
N1 C12 1.343(3) . ?
N1 Cu1 2.003(2) 8_656 ?
O4 N3 1.243(3) . ?
O2 Cu1 1.9478(17) 5_566 ?
N2 C13 1.328(4) . ?
N2 C17 1.336(3) . ?
N2 Cu1 2.005(2) 3_546 ?
C5 C4 1.395(4) . ?
C5 C6 1.403(4) . ?
C2 C7 1.382(4) . ?
O5 N3 1.227(3) . ?
C11 C12 1.379(4) . ?
C13 C14 1.380(4) . ?
C8 C9 1.374(4) . ?
C16 C17 1.369(4) . ?
C6 C7 1.399(4) . ?

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
C9 C10 C11 117.3(3) . . ?
C9 C10 C4 121.9(2) . . ?
C11 C10 C4 120.6(2) . . ?
C14 C15 C16 117.0(3) . . ?
C14 C15 C6 120.3(3) . . ?
C16 C15 C6 122.7(3) . . ?
O1 C1 O2 126.7(2) . . ?
O1 C1 C2 118.9(2) . . ?
O2 C1 C2 114.4(2) . . ?
O2 Cu1 N1 92.19(8) 5_566 8_655 ?
O2 Cu1 N2 86.44(8) 5_566 3_556 ?
N1 Cu1 N2 169.82(9) 8_655 3_556 ?
O2 Cu1 O3 163.65(8) 5_566 . ?
N1 Cu1 O3 88.93(8) 8_655 . ?
N2 Cu1 O3 89.58(8) 3_556 . ?
O2 Cu1 O1 104.40(7) 5_566 . ?
N1 Cu1 O1 97.57(8) 8_655 . ?
N2 Cu1 O1 92.54(9) 3_556 . ?
O3 Cu1 O1 91.60(7) . . ?
N3 O3 Cu1 112.44(16) . . ?
C2 C3 C4 120.4(2) . . ?
C8 N1 C12 116.7(2) . . ?
C8 N1 Cu1 121.69(18) . 8_656 ?
C12 N1 Cu1 120.66(18) . 8_656 ?
C1 O1 Cu1 147.57(18) . . ?
C1 O2 Cu1 127.28(17) . 5_566 ?
C13 N2 C17 117.4(2) . . ?
C13 N2 Cu1 121.6(2) . 3_546 ?
C17 N2 Cu1 120.48(19) . 3_546 ?
C4 C5 C6 120.7(3) . . ?
C7 C2 C3 120.3(2) . . ?
C7 C2 C1 121.0(2) . . ?
C3 C2 C1 118.7(2) . . ?
O5 N3 O4 122.5(3) . . ?
O5 N3 O3 119.2(2) . . ?
O4 N3 O3 118.3(2) . . ?
C12 C11 C10 119.3(3) . . ?
N2 C13 C14 123.1(3) . . ?
N1 C8 C9 123.6(3) . . ?
C8 C9 C10 119.5(3) . . ?
C17 C16 C15 119.8(3) . . ?
C5 C4 C3 119.0(2) . . ?
C5 C4 C10 121.1(2) . . ?
C3 C4 C10 119.8(2) . . ?
N1 C12 C11 123.4(3) . . ?
C15 C14 C13 119.7(3) . . ?
N2 C17 C16 123.0(3) . . ?
C7 C6 C5 119.2(3) . . ?
C7 C6 C15 120.9(2) . . ?
C5 C6 C15 119.9(2) . . ?
C2 C7 C6 120.4(3) . . ?

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
O2 Cu1 O3 N3 -21.8(4) 5_566 . . . ?
N1 Cu1 O3 N3 72.39(18) 8_655 . . . ?
N2 Cu1 O3 N3 -97.53(18) 3_556 . . . ?
O1 Cu1 O3 N3 169.93(18) . . . . ?
O2 C1 O1 Cu1 -85.9(4) . . . . ?
C2 C1 O1 Cu1 95.5(3) . . . . ?
O2 Cu1 O1 C1 97.3(3) 5_566 . . . ?
N1 Cu1 O1 C1 3.1(3) 8_655 . . . ?
N2 Cu1 O1 C1 -175.7(3) 3_556 . . . ?
O3 Cu1 O1 C1 -86.1(3) . . . . ?
O1 C1 O2 Cu1 -2.8(4) . . . 5_566 ?
C2 C1 O2 Cu1 175.82(16) . . . 5_566 ?
C4 C3 C2 C7 1.5(4) . . . . ?
C4 C3 C2 C1 -179.3(2) . . . . ?
O1 C1 C2 C7 164.8(3) . . . . ?
O2 C1 C2 C7 -13.9(4) . . . . ?
O1 C1 C2 C3 -14.3(4) . . . . ?
O2 C1 C2 C3 166.9(2) . . . . ?
Cu1 O3 N3 O5 -173.4(2) . . . . ?
Cu1 O3 N3 O4 6.3(3) . . . . ?
C9 C10 C11 C12 -4.8(4) . . . . ?
C4 C10 C11 C12 170.9(3) . . . . ?
C17 N2 C13 C14 -0.4(5) . . . . ?
Cu1 N2 C13 C14 171.5(3) 3_546 . . . ?
C12 N1 C8 C9 -3.3(4) . . . . ?
Cu1 N1 C8 C9 165.7(2) 8_656 . . . ?
N1 C8 C9 C10 1.5(5) . . . . ?
C11 C10 C9 C8 2.7(4) . . . . ?
C4 C10 C9 C8 -173.0(3) . . . . ?
C14 C15 C16 C17 -0.2(4) . . . . ?
C6 C15 C16 C17 177.6(3) . . . . ?
C6 C5 C4 C3 -2.3(4) . . . . ?
C6 C5 C4 C10 173.7(3) . . . . ?
C2 C3 C4 C5 0.1(4) . . . . ?
C2 C3 C4 C10 -175.9(2) . . . . ?
C9 C10 C4 C5 -23.1(4) . . . . ?
C11 C10 C4 C5 161.4(3) . . . . ?
C9 C10 C4 C3 152.8(3) . . . . ?
C11 C10 C4 C3 -22.7(4) . . . . ?
C8 N1 C12 C11 0.9(4) . . . . ?
Cu1 N1 C12 C11 -168.2(2) 8_656 . . . ?
C10 C11 C12 N1 3.2(5) . . . . ?
C16 C15 C14 C13 0.8(5) . . . . ?
C6 C15 C14 C13 -177.0(3) . . . . ?
N2 C13 C14 C15 -0.5(6) . . . . ?
C13 N2 C17 C16 1.1(4) . . . . ?
Cu1 N2 C17 C16 -170.9(2) 3_546 . . . ?
C15 C16 C17 N2 -0.8(5) . . . . ?
C4 C5 C6 C7 2.8(4) . . . . ?
C4 C5 C6 C15 -175.7(3) . . . . ?
C14 C15 C6 C7 -41.6(4) . . . . ?
C16 C15 C6 C7 140.7(3) . . . . ?
C14 C15 C6 C5 136.8(3) . . . . ?
C16 C15 C6 C5 -40.8(4) . . . . ?
C3 C2 C7 C6 -1.0(4) . . . . ?
C1 C2 C7 C6 179.8(3) . . . . ?
C5 C6 C7 C2 -1.1(4) . . . . ?
C15 C6 C7 C2 177.3(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        27.45
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         0.642
_refine_diff_density_min         -0.446
_refine_diff_density_rms         0.075



_vrf_PLAT430_p                   
;
PROBLEM: Short Inter D...A Contact  O2     ..  N2      ..     2.71 Ang.
         Short Inter D...A Contact  O2     ..  N1      ..     2.85 Ang.   
RESPONSE:  
O2 is the oxygen atom of carboxyl group. N1,N2 is the nitrogen atom from one terminal pyridine ring.And the distance between them is reasonable.
;
# end Validation Reply Form
