# Electronic Supplementary Material for CrystEngComm
# This journal is (c) The Royal Society of Chemistry 2009

data_global
_journal_name_full               CrystEngComm

_journal_coden_Cambridge         1350

_publ_contact_author_name        'Guo-Cong Guo'
_publ_contact_author_email       GCGUO@FJIRSM.AC.CN

_publ_section_title              
;
A novel heterometal-organic coordination polymer
with chelidamic acid: nonlinear optical and magnetic properties
;
loop_
_publ_author_name
'Guo-Cong Guo'
'Jin-Shun Huang'
'Ying-Bing Lu'
'Ming-Sheng Wang'
;
Zhang-Jing Zhang
;
'Xing Zhang'
'Guo-Wei Zhou'
'Wei-Wei Zhou'
'Jian-Ping Zou'

# Attachment 'compound1.cif'

data_a
_database_code_depnum_ccdc_archive 'CCDC 705787'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          'not measured'
_chemical_formula_moiety         'C14 H9 Ag Cu2 N2 O12'
_chemical_formula_sum            'C14 H9 Ag Cu2 N2 O12'
_chemical_formula_weight         632.18
_symmetry_space_group_name_Hall  '-P 2yn'

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'
Ag Ag -0.8971 1.1015 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 21/n'

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

_cell_length_a                   8.4438(3)
_cell_length_b                   10.0791(4)
_cell_length_c                   19.4100(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 92.2640(10)
_cell_angle_gamma                90.00
_cell_volume                     1650.62(10)
_cell_formula_units_Z            4
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    3870
_cell_measurement_theta_min      2.1211
_cell_measurement_theta_max      26.2835

_exptl_crystal_description       prism
_exptl_crystal_colour            'pale blue'
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.28
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    2.544
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1232
_exptl_absorpt_coefficient_mu    3.808
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.700065
_exptl_absorpt_correction_T_max  1.000000
_exptl_absorpt_process_details   'SADABS(Siemens SMART CCD)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      293(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  'Siemens SMART CCD'
_diffrn_measurement_method       ω
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            5189
_diffrn_reflns_av_R_equivalents  0.0200
_diffrn_reflns_av_sigmaI/netI    0.0348
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -10
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_theta_min         2.10
_diffrn_reflns_theta_max         25.04
_reflns_number_total             2900
_reflns_number_gt                2412
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Siemens SMART'
_computing_cell_refinement       'Siemens SMART & SAINT'
_computing_data_reduction        'Siemens SMART'
_computing_structure_solution    'Siemens SHELXTLTM 5'
_computing_structure_refinement  'Siemens SHELXTLTM 5'
_computing_molecular_graphics    'Siemens SHELXTLTM 5'
_computing_publication_material  'Siemens SHELXTLTM 5'

_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)+(0.0483P)²+1.1541P] 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     SHELXL
_refine_ls_extinction_coef       0.0027(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_number_reflns         2900
_refine_ls_number_parameters     293
_refine_ls_number_restraints     6
_refine_ls_R_factor_all          0.0382
_refine_ls_R_factor_gt           0.0301
_refine_ls_wR_factor_ref         0.0795
_refine_ls_wR_factor_gt          0.0747
_refine_ls_goodness_of_fit_ref   1.009
_refine_ls_restrained_S_all      1.009
_refine_ls_shift/su_max          0.003
_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
Ag1 Ag 0.41431(5) 0.72622(3) 0.129132(17) 0.03484(14) Uani 1 1 d . . .
Cu1 Cu 0.87233(6) 1.03583(5) 0.22900(2) 0.02152(15) Uani 1 1 d . . .
Cu2 Cu 0.31772(6) 0.45460(5) 0.03570(2) 0.02573(16) Uani 1 1 d . . .
O1 O 0.1842(4) 0.3614(3) -0.03517(14) 0.0344(8) Uani 1 1 d . . .
O1W O 0.1489(4) 0.6095(4) 0.1160(2) 0.0536(10) Uani 1 1 d D . .
H1WA H 0.115(8) 0.565(5) 0.151(3) 0.080 Uiso 1 1 d D . .
H1WB H 0.097(8) 0.682(4) 0.125(3) 0.080 Uiso 1 1 d D . .
O2 O 0.0453(4) 0.1754(3) -0.05234(16) 0.0384(8) Uani 1 1 d . . .
O2W O 0.7142(4) 1.1318(3) 0.30754(16) 0.0363(8) Uani 1 1 d D . .
H2WA H 0.708(7) 1.2144(19) 0.308(2) 0.054 Uiso 1 1 d D . .
H2WB H 0.691(7) 1.105(4) 0.3466(15) 0.054 Uiso 1 1 d D . .
O3 O 0.5352(4) 0.3893(3) 0.22201(13) 0.0261(6) Uani 1 1 d . . .
O4 O 0.4619(3) 0.4874(3) 0.12244(13) 0.0237(6) Uani 1 1 d . . .
O5 O 0.2488(4) -0.0656(3) 0.17648(14) 0.0303(7) Uani 1 1 d . . .
H5A H 0.3062 -0.0703 0.2115 0.045 Uiso 1 1 calc R . .
O6 O 0.5637(4) 0.8959(3) 0.08539(14) 0.0295(7) Uani 1 1 d . . .
O7 O 0.7196(4) 0.9104(3) 0.18103(13) 0.0268(7) Uani 1 1 d . . .
O8 O 1.0726(3) 1.3989(3) 0.20690(13) 0.0246(6) Uani 1 1 d . . .
O9 O 1.0226(3) 1.1956(3) 0.24607(13) 0.0230(6) Uani 1 1 d . . .
O10 O 0.6378(3) 1.3754(3) -0.00249(13) 0.0250(6) Uani 1 1 d . . .
N1 N 0.2997(4) 0.2892(3) 0.08075(16) 0.0200(7) Uani 1 1 d . . .
N2 N 0.8179(4) 1.1423(3) 0.15190(16) 0.0190(7) Uani 1 1 d . . .
C1 C 0.2103(5) 0.1945(4) 0.05051(19) 0.0200(8) Uani 1 1 d . . .
C2 C 0.1915(5) 0.0726(4) 0.0817(2) 0.0236(9) Uani 1 1 d . . .
H2A H 0.1297 0.0063 0.0608 0.028 Uiso 1 1 calc R . .
C3 C 0.2691(5) 0.0527(4) 0.1460(2) 0.0216(8) Uani 1 1 d . . .
C4 C 0.3613(5) 0.1523(4) 0.17682(19) 0.0208(8) Uani 1 1 d . . .
H4A H 0.4130 0.1396 0.2195 0.025 Uiso 1 1 calc R . .
C5 C 0.3732(5) 0.2698(4) 0.14199(19) 0.0185(8) Uani 1 1 d . . .
C6 C 0.1388(5) 0.2435(4) -0.0180(2) 0.0267(9) Uani 1 1 d . . .
C7 C 0.4644(5) 0.3916(4) 0.16431(18) 0.0194(8) Uani 1 1 d . . .
C8 C 0.7118(5) 1.0937(4) 0.10557(19) 0.0176(8) Uani 1 1 d . . .
C9 C 0.6555(5) 1.1683(4) 0.05066(18) 0.0196(8) Uani 1 1 d . . .
H9A H 0.5843 1.1324 0.0180 0.023 Uiso 1 1 calc R . .
C10 C 0.7080(5) 1.3005(4) 0.04486(18) 0.0202(8) Uani 1 1 d . . .
C11 C 0.8285(5) 1.3460(4) 0.09233(19) 0.0198(8) Uani 1 1 d . . .
H11A H 0.8727 1.4299 0.0876 0.024 Uiso 1 1 calc R . .
C12 C 0.8787(5) 1.2634(4) 0.14545(19) 0.0184(8) Uani 1 1 d . . .
C13 C 0.6592(5) 0.9550(4) 0.12420(19) 0.0212(9) Uani 1 1 d . . .
C14 C 1.0016(5) 1.2916(4) 0.20370(19) 0.0188(8) Uani 1 1 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
Ag1 O6 2.306(3) . ?
Ag1 O4 2.445(3) . ?
Ag1 O9 2.479(3) 2_645 ?
Ag1 O1W 2.535(4) . ?
Cu1 N2 1.884(3) . ?
Cu1 O3 1.907(3) 2_655 ?
Cu1 O7 2.008(3) . ?
Cu1 O9 2.069(3) . ?
Cu1 O2W 2.281(3) . ?
Cu2 O10 1.874(3) 3_675 ?
Cu2 N1 1.891(3) . ?
Cu2 O1 1.981(3) . ?
Cu2 O4 2.065(3) . ?
O1 C6 1.296(5) . ?
O1W H1WA 0.86(3) . ?
O1W H1WB 0.87(3) . ?
O2 C6 1.224(5) . ?
O2W H2WA 0.834(19) . ?
O2W H2WB 0.837(19) . ?
O3 C7 1.249(4) . ?
O3 Cu1 1.907(3) 2_645 ?
O4 C7 1.261(5) . ?
O5 C3 1.345(5) . ?
O5 H5A 0.8200 . ?
O6 C13 1.235(5) . ?
O7 C13 1.279(5) . ?
O8 C14 1.237(5) . ?
O9 C14 1.277(5) . ?
O9 Ag1 2.479(3) 2_655 ?
O10 C10 1.313(5) . ?
O10 Cu2 1.874(3) 3_675 ?
N1 C5 1.334(5) . ?
N1 C1 1.338(5) . ?
N2 C12 1.333(5) . ?
N2 C8 1.337(5) . ?
C1 C2 1.382(5) . ?
C1 C6 1.521(5) . ?
C2 C3 1.402(5) . ?
C2 H2A 0.9300 . ?
C3 C4 1.391(5) . ?
C4 C5 1.369(5) . ?
C4 H4A 0.9300 . ?
C5 C7 1.504(5) . ?
C8 C9 1.374(5) . ?
C8 C13 1.514(5) . ?
C9 C10 1.410(5) . ?
C9 H9A 0.9300 . ?
C10 C11 1.421(5) . ?
C11 C12 1.378(5) . ?
C11 H11A 0.9300 . ?
C12 C14 1.531(5) . ?

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
O6 Ag1 O4 128.09(11) . . ?
O6 Ag1 O9 110.63(9) . 2_645 ?
O4 Ag1 O9 84.27(9) . 2_645 ?
O6 Ag1 O1W 143.25(11) . . ?
O4 Ag1 O1W 71.60(12) . . ?
O9 Ag1 O1W 101.27(11) 2_645 . ?
N2 Cu1 O3 156.88(13) . 2_655 ?
N2 Cu1 O7 81.84(12) . . ?
O3 Cu1 O7 89.22(11) 2_655 . ?
N2 Cu1 O9 79.20(12) . . ?
O3 Cu1 O9 106.67(11) 2_655 . ?
O7 Cu1 O9 160.52(10) . . ?
N2 Cu1 O2W 99.13(13) . . ?
O3 Cu1 O2W 103.53(12) 2_655 . ?
O7 Cu1 O2W 101.22(13) . . ?
O9 Cu1 O2W 86.24(12) . . ?
O10 Cu2 N1 170.35(12) 3_675 . ?
O10 Cu2 O1 108.13(11) 3_675 . ?
N1 Cu2 O1 81.31(12) . . ?
O10 Cu2 O4 90.84(11) 3_675 . ?
N1 Cu2 O4 79.61(12) . . ?
O1 Cu2 O4 160.58(11) . . ?
C6 O1 Cu2 115.0(2) . . ?
Ag1 O1W H1WA 118(5) . . ?
Ag1 O1W H1WB 92(5) . . ?
H1WA O1W H1WB 96(5) . . ?
Cu1 O2W H2WA 118(4) . . ?
Cu1 O2W H2WB 129(4) . . ?
H2WA O2W H2WB 107(3) . . ?
C7 O3 Cu1 127.2(3) . 2_645 ?
C7 O4 Cu2 113.4(2) . . ?
C7 O4 Ag1 135.9(2) . . ?
Cu2 O4 Ag1 96.20(10) . . ?
C3 O5 H5A 109.5 . . ?
C13 O6 Ag1 119.1(2) . . ?
C13 O7 Cu1 113.9(2) . . ?
C14 O9 Cu1 114.7(2) . . ?
C14 O9 Ag1 123.6(2) . 2_655 ?
Cu1 O9 Ag1 111.10(11) . 2_655 ?
C10 O10 Cu2 132.5(3) . 3_675 ?
C5 N1 C1 121.4(3) . . ?
C5 N1 Cu2 119.9(3) . . ?
C1 N1 Cu2 118.7(3) . . ?
C12 N2 C8 121.5(3) . . ?
C12 N2 Cu1 120.9(2) . . ?
C8 N2 Cu1 117.5(3) . . ?
N1 C1 C2 121.0(3) . . ?
N1 C1 C6 110.5(3) . . ?
C2 C1 C6 128.5(3) . . ?
C1 C2 C3 117.4(4) . . ?
C1 C2 H2A 121.3 . . ?
C3 C2 H2A 121.3 . . ?
O5 C3 C4 122.0(4) . . ?
O5 C3 C2 117.1(3) . . ?
C4 C3 C2 120.9(4) . . ?
C5 C4 C3 117.6(4) . . ?
C5 C4 H4A 121.2 . . ?
C3 C4 H4A 121.2 . . ?
N1 C5 C4 121.8(4) . . ?
N1 C5 C7 110.6(3) . . ?
C4 C5 C7 127.6(3) . . ?
O2 C6 O1 124.4(4) . . ?
O2 C6 C1 121.3(4) . . ?
O1 C6 C1 114.3(3) . . ?
O3 C7 O4 125.9(4) . . ?
O3 C7 C5 117.7(3) . . ?
O4 C7 C5 116.4(3) . . ?
N2 C8 C9 121.5(3) . . ?
N2 C8 C13 111.9(3) . . ?
C9 C8 C13 126.5(3) . . ?
C8 C9 C10 118.6(3) . . ?
C8 C9 H9A 120.7 . . ?
C10 C9 H9A 120.7 . . ?
O10 C10 C9 117.7(3) . . ?
O10 C10 C11 124.1(3) . . ?
C9 C10 C11 118.2(3) . . ?
C12 C11 C10 118.8(3) . . ?
C12 C11 H11A 120.6 . . ?
C10 C11 H11A 120.6 . . ?
N2 C12 C11 121.0(3) . . ?
N2 C12 C14 110.7(3) . . ?
C11 C12 C14 128.3(3) . . ?
O6 C13 O7 125.8(4) . . ?
O6 C13 C8 119.4(3) . . ?
O7 C13 C8 114.8(3) . . ?
O8 C14 O9 125.1(3) . . ?
O8 C14 C12 120.8(3) . . ?
O9 C14 C12 114.1(3) . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O1W H1WA O8 0.86(3) 2.04(3) 2.850(5) 156(6) 1_445
O1W H1WB O2 0.87(3) 2.32(5) 2.959(5) 131(6) 3_565
O2W H2WA O7 0.834(19) 2.08(3) 2.870(4) 159(6) 2_655
O5 H5A O8 0.82 1.88 2.694(4) 173.2 2_635

_diffrn_measured_fraction_theta_max 0.993
_diffrn_reflns_theta_full        25.04
_diffrn_measured_fraction_theta_full 0.993
_refine_diff_density_max         1.310
_refine_diff_density_min         -0.803
_refine_diff_density_rms         0.110


