# Electronic Supplementary Material (ESI) for CrystEngComm
# This journal is © The Royal Society of Chemistry 2012


data_global
_journal_name_full               CrystEngComm
_journal_coden_cambridge         1350
#TrackingRef 'cif-LinCheng-120106.txt'

_publ_requested_coeditor_name    ?
_publ_contact_letter             
;
Dear Sir or Madam:

Please consider this CIF as a supplmentary data for a paper submitted to
CrystEngComm
Thanks.

Lin Cheng
;
#=================================================================

# 2. PROCESSING SUMMARY (IUCr Office Use Only)

_journal_date_recd_electronic    ?

_journal_date_to_coeditor        ?
_journal_date_from_coeditor      ?
_journal_date_accepted           ?

_journal_date_printers_first     ?
_journal_date_printers_final     ?
_journal_date_proofs_out         ?
_journal_date_proofs_in          ?

_journal_coeditor_name           ?
_journal_coeditor_code           ?
_journal_coeditor_notes          ?

_journal_techeditor_code         ?
_journal_techeditor_notes        ?

_journal_coden_ASTM              ?
_journal_year                    ?
_journal_volume                  ?
_journal_issue                   ?
_journal_page_first              ?
_journal_page_last               ?

_journal_suppl_publ_number       ?
_journal_suppl_publ_pages        ?

#=======================================================

# 3. TITLE AND AUTHOR LIST

_publ_section_title              
;
Metal-directed one-dimensional chiral zigzag chain
and right-handed 6~1~ helix with
multiple chiral components: Fluorescence and NLO properties
;
loop_
_publ_author_name
_publ_author_address
'Lin Cheng'
; School of Chemistry and Chemical Engineering
Southeast University
Nanjing 211189
P. R. China
;
'Liming Zhang'
; School of Chemistry and Chemical Engineering
Southeast University
Nanjing 211189
P. R. China
;
'Shaohua Gou'
; School of Chemistry and Chemical Engineering
Southeast University
Nanjing 211189
P. R. China
;
'Qingna Cao' ''
'Jianquan Wang' ''
'Lei Fang' ''
_publ_contact_author_email       cep02chl@yahoo.com.cn
_publ_contact_author_name        'Lin Cheng'

#===============================END

data_1
_database_code_depnum_ccdc_archive 'CCDC 861319'
#TrackingRef 'cif-LinCheng-120106.txt'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C19 H26 Ag N5 O4'
_chemical_formula_weight         496.32
_chemical_absolute_configuration .

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'
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   C2

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

_cell_length_a                   13.419(3)
_cell_length_b                   14.427(3)
_cell_length_c                   10.793(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.773(3)
_cell_angle_gamma                90.00
_cell_volume                     2089.4(7)
_cell_formula_units_Z            4
_cell_measurement_temperature    123(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.23
_exptl_crystal_size_min          0.19
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.578
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1016
_exptl_absorpt_coefficient_mu    1.000
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.7882
_exptl_absorpt_correction_T_max  0.8328
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      123(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 SMART APEX CCD'
_diffrn_measurement_method       '\f and \w scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            7045
_diffrn_reflns_av_R_equivalents  0.0217
_diffrn_reflns_av_sigmaI/netI    0.0369
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.79
_diffrn_reflns_theta_max         26.00
_reflns_number_total             3757
_reflns_number_gt                3627
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART (Bruker, 2000)'
_computing_cell_refinement       'SMART (Bruker, 2000)'
_computing_data_reduction        'SAINT (Bruker, 2000)'
_computing_structure_solution    'SHELXTL (Bruker, 2000)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
;
ORTEPIII (Burnett & Johnson, 1996); ORTEP-3 for Windows (Farrugia, 1997);
PLATON (Spek, 2009)
;
_computing_publication_material  'SHELXTL (Bruker, 2000)'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0641P)^2^+8.2912P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.17(6)
_refine_ls_number_reflns         3757
_refine_ls_number_parameters     263
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0470
_refine_ls_R_factor_gt           0.0457
_refine_ls_wR_factor_ref         0.1264
_refine_ls_wR_factor_gt          0.1252
_refine_ls_goodness_of_fit_ref   1.138
_refine_ls_restrained_S_all      1.138
_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
Ag1 Ag 0.0000 -0.80776(4) -0.5000 0.0335(2) Uani 1 2 d S . .
Ag2 Ag 0.0000 -1.00845(4) 0.0000 0.0338(2) Uani 1 2 d S . .
C1 C -0.0806(6) -0.9863(6) -0.3444(7) 0.030(2) Uani 1 1 d . . .
H1A H -0.0285 -1.0172 -0.3867 0.036 Uiso 1 1 calc R . .
C2 C -0.1761(6) -0.8521(8) -0.3194(9) 0.044(2) Uani 1 1 d . . .
H2A H -0.1953 -0.7915 -0.3445 0.053 Uiso 1 1 calc R . .
C3 C -0.2273(7) -0.8976(9) -0.2189(11) 0.053(3) Uani 1 1 d . . .
H3A H -0.2753 -0.8656 -0.1712 0.064 Uiso 1 1 calc R . .
C4 C -0.2039(7) -0.9887(8) -0.1947(8) 0.043(2) Uani 1 1 d . . .
H4A H -0.2410 -1.0206 -0.1336 0.051 Uiso 1 1 calc R . .
C5 C -0.1308(6) -1.0353(7) -0.2535(7) 0.031(2) Uani 1 1 d . . .
C6 C -0.0984(6) -1.1304(7) -0.2246(7) 0.0313(19) Uani 1 1 d . . .
H6A H -0.1513 -1.1743 -0.2508 0.038 Uiso 1 1 calc R . .
H6B H -0.0379 -1.1448 -0.2723 0.038 Uiso 1 1 calc R . .
C7 C -0.0187(7) -1.2271(7) -0.0663(8) 0.0290(19) Uani 1 1 d . . .
H7A H 0.0415 -1.2245 -0.1199 0.035 Uiso 1 1 calc R . .
C8 C -0.0739(6) -1.3178(6) -0.0987(6) 0.0386(17) Uani 1 1 d . . .
H8A H -0.1369 -1.3200 -0.0521 0.046 Uiso 1 1 calc R . .
H8B H -0.0913 -1.3173 -0.1882 0.046 Uiso 1 1 calc R . .
C9 C -0.0134(8) -1.4056(8) -0.0697(10) 0.043(2) Uani 1 1 d . . .
H9A H 0.0481 -1.4064 -0.1193 0.051 Uiso 1 1 calc R . .
H9B H -0.0531 -1.4614 -0.0908 0.051 Uiso 1 1 calc R . .
C10 C -0.0861(5) -0.8327(7) 0.1548(7) 0.032(3) Uani 1 1 d . . .
H10A H -0.0425 -0.7977 0.1045 0.038 Uiso 1 1 calc R . .
C11 C -0.1631(5) -0.9668(7) 0.2004(7) 0.0327(18) Uani 1 1 d . . .
H11A H -0.1740 -1.0306 0.1825 0.039 Uiso 1 1 calc R . .
C12 C -0.2127(7) -0.9293(9) 0.2945(9) 0.048(2) Uani 1 1 d . . .
H12A H -0.2580 -0.9661 0.3403 0.058 Uiso 1 1 calc R . .
C13 C -0.1986(6) -0.8375(7) 0.3256(7) 0.033(2) Uani 1 1 d . . .
H13A H -0.2318 -0.8100 0.3934 0.040 Uiso 1 1 calc R . .
C14 C -0.1341(6) -0.7879(6) 0.2535(8) 0.028(2) Uani 1 1 d . . .
C15 C -0.1166(6) -0.6839(7) 0.2778(7) 0.0310(18) Uani 1 1 d . . .
H15A H -0.0996 -0.6521 0.1996 0.037 Uiso 1 1 calc R . .
H15B H -0.1778 -0.6553 0.3108 0.037 Uiso 1 1 calc R . .
C16 C -0.0393(7) -0.5878(8) 0.4487(8) 0.030(2) Uani 1 1 d . . .
H16A H -0.1062 -0.5881 0.4885 0.036 Uiso 1 1 calc R . .
C17 C -0.0331(6) -0.5015(6) 0.3688(6) 0.0339(14) Uani 1 1 d . . .
H17A H -0.0877 -0.5021 0.3062 0.041 Uiso 1 1 calc R . .
H17B H 0.0310 -0.5011 0.3244 0.041 Uiso 1 1 calc R . .
C18 C -0.0410(7) -0.4140(7) 0.4490(9) 0.033(2) Uani 1 1 d . . .
H18A H -0.1074 -0.4116 0.4877 0.039 Uiso 1 1 calc R . .
H18B H -0.0337 -0.3583 0.3962 0.039 Uiso 1 1 calc R . .
C19 C 0.3451(8) -0.6673(8) 0.4197(12) 0.070(4) Uani 1 1 d . . .
H19A H 0.3985 -0.6237 0.4419 0.105 Uiso 1 1 calc R . .
H19B H 0.3525 -0.7239 0.4691 0.105 Uiso 1 1 calc R . .
H19C H 0.2804 -0.6388 0.4364 0.105 Uiso 1 1 calc R . .
N1 N -0.1013(5) -0.8960(6) -0.3772(6) 0.0317(16) Uani 1 1 d . . .
N2 N -0.0770(4) -1.1434(4) -0.0930(5) 0.0306(11) Uani 1 1 d . . .
N3 N -0.0991(5) -0.9202(6) 0.1299(7) 0.0347(17) Uani 1 1 d . . .
N4 N -0.0316(4) -0.6740(4) 0.3712(5) 0.0292(11) Uani 1 1 d . . .
N5 N 0.1530(5) -0.6520(7) 0.0962(7) 0.047(2) Uani 1 1 d . . .
O1 O 0.1563(10) -0.6302(11) 0.2241(11) 0.134(6) Uani 1 1 d . . .
H1B H 0.2122 -0.6451 0.2539 0.200 Uiso 1 1 calc R . .
O2 O 0.2376(6) -0.6638(6) 0.0598(9) 0.126(4) Uani 1 1 d . . .
O3 O 0.0690(7) -0.6493(7) 0.0521(9) 0.109(3) Uani 1 1 d . . .
O4 O 0.3506(4) -0.6883(6) 0.2991(6) 0.0470(16) Uani 1 1 d . . .

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
Ag1 0.0444(4) 0.0268(5) 0.0291(4) 0.000 -0.0046(3) 0.000
Ag2 0.0424(4) 0.0304(5) 0.0284(4) 0.000 -0.0033(3) 0.000
C1 0.034(4) 0.026(6) 0.031(4) 0.003(3) -0.007(3) 0.003(3)
C2 0.042(4) 0.038(5) 0.052(5) -0.002(4) -0.005(3) 0.001(4)
C3 0.046(5) 0.047(6) 0.068(6) -0.002(5) 0.023(4) 0.013(4)
C4 0.048(5) 0.044(6) 0.036(4) 0.001(4) -0.004(3) 0.000(4)
C5 0.034(4) 0.041(6) 0.016(3) -0.013(3) -0.010(3) 0.000(3)
C6 0.034(4) 0.036(5) 0.023(3) 0.009(3) -0.012(3) -0.008(3)
C7 0.043(4) 0.021(4) 0.024(3) 0.002(3) 0.007(3) -0.007(3)
C8 0.064(4) 0.036(4) 0.015(3) 0.004(3) -0.003(3) -0.012(4)
C9 0.059(6) 0.031(5) 0.038(5) -0.001(4) 0.000(4) 0.001(4)
C10 0.027(3) 0.045(8) 0.023(4) 0.007(3) 0.000(3) -0.002(3)
C11 0.032(4) 0.031(4) 0.035(4) -0.006(3) -0.002(3) -0.014(3)
C12 0.049(5) 0.043(6) 0.053(5) 0.001(4) 0.013(4) -0.008(4)
C13 0.038(4) 0.040(5) 0.021(3) 0.001(3) 0.014(3) 0.001(3)
C14 0.025(3) 0.026(5) 0.033(4) -0.006(3) -0.011(3) 0.004(3)
C15 0.029(3) 0.032(5) 0.032(4) 0.004(3) -0.010(3) 0.007(3)
C16 0.028(3) 0.038(5) 0.022(3) -0.005(3) -0.005(3) 0.009(3)
C17 0.051(4) 0.028(3) 0.023(3) 0.002(3) -0.002(3) -0.001(3)
C18 0.042(4) 0.029(4) 0.027(4) 0.008(3) -0.002(3) 0.007(3)
C19 0.074(7) 0.033(6) 0.105(9) 0.003(6) 0.050(6) -0.004(5)
N1 0.034(3) 0.032(5) 0.029(3) 0.003(3) -0.004(3) 0.005(3)
N2 0.038(3) 0.034(3) 0.020(2) 0.004(2) -0.005(2) 0.000(2)
N3 0.037(3) 0.029(5) 0.038(4) 0.002(4) -0.003(3) 0.005(3)
N4 0.038(3) 0.026(3) 0.023(3) 0.000(2) -0.008(2) -0.002(2)
N5 0.042(4) 0.061(6) 0.039(3) 0.008(4) -0.016(3) -0.002(4)
O1 0.161(11) 0.133(12) 0.107(8) -0.047(8) 0.041(7) -0.067(9)
O2 0.124(6) 0.078(5) 0.181(8) -0.076(6) 0.132(6) -0.062(5)
O3 0.107(6) 0.094(7) 0.126(7) -0.029(6) -0.032(5) -0.017(5)
O4 0.043(3) 0.057(4) 0.041(3) -0.007(3) 0.013(2) -0.002(3)

_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 N1 2.296(7) . ?
Ag1 N1 2.296(7) 2_554 ?
Ag1 N4 2.413(5) 2 ?
Ag1 N4 2.413(5) 1_554 ?
Ag2 N3 2.325(7) . ?
Ag2 N3 2.325(7) 2 ?
Ag2 N2 2.416(6) . ?
Ag2 N2 2.416(6) 2 ?
C1 N1 1.377(12) . ?
C1 C5 1.391(12) . ?
C1 H1A 0.9500 . ?
C2 N1 1.348(11) . ?
C2 C3 1.450(15) . ?
C2 H2A 0.9500 . ?
C3 C4 1.375(17) . ?
C3 H3A 0.9500 . ?
C4 C5 1.355(13) . ?
C4 H4A 0.9500 . ?
C5 C6 1.471(14) . ?
C6 N2 1.458(8) . ?
C6 H6A 0.9900 . ?
C6 H6B 0.9900 . ?
C7 N2 1.465(12) . ?
C7 C7 1.51(2) 2 ?
C7 C8 1.542(12) . ?
C7 H7A 1.0000 . ?
C8 C9 1.534(15) . ?
C8 H8A 0.9900 . ?
C8 H8B 0.9900 . ?
C9 C9 1.54(2) 2 ?
C9 H9A 0.9900 . ?
C9 H9B 0.9900 . ?
C10 N3 1.301(13) . ?
C10 C14 1.409(12) . ?
C10 H10A 0.9500 . ?
C11 N3 1.337(11) . ?
C11 C12 1.337(13) . ?
C11 H11A 0.9500 . ?
C12 C13 1.378(16) . ?
C12 H12A 0.9500 . ?
C13 C14 1.373(12) . ?
C13 H13A 0.9500 . ?
C14 C15 1.541(13) . ?
C15 N4 1.519(9) . ?
C15 H15A 0.9900 . ?
C15 H15B 0.9900 . ?
C16 N4 1.503(11) . ?
C16 C16 1.520(17) 2_556 ?
C16 C17 1.517(13) . ?
C16 H16A 1.0000 . ?
C17 C18 1.536(13) . ?
C17 H17A 0.9900 . ?
C17 H17B 0.9900 . ?
C18 C18 1.545(19) 2_556 ?
C18 H18A 0.9900 . ?
C18 H18B 0.9900 . ?
C19 O4 1.340(14) . ?
C19 H19A 0.9800 . ?
C19 H19B 0.9800 . ?
C19 H19C 0.9800 . ?
N4 Ag1 2.413(5) 1_556 ?
N5 O3 1.219(11) . ?
N5 O2 1.219(10) . ?
N5 O1 1.416(13) . ?
O1 H1B 0.8400 . ?

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 Ag1 N1 112.6(4) . 2_554 ?
N1 Ag1 N4 102.2(2) . 2 ?
N1 Ag1 N4 132.5(2) 2_554 2 ?
N1 Ag1 N4 132.5(2) . 1_554 ?
N1 Ag1 N4 102.2(2) 2_554 1_554 ?
N4 Ag1 N4 73.8(2) 2 1_554 ?
N3 Ag2 N3 113.6(4) . 2 ?
N3 Ag2 N2 116.6(2) . . ?
N3 Ag2 N2 115.8(2) 2 . ?
N3 Ag2 N2 115.8(2) . 2 ?
N3 Ag2 N2 116.6(2) 2 2 ?
N2 Ag2 N2 72.6(3) . 2 ?
N1 C1 C5 124.3(8) . . ?
N1 C1 H1A 117.8 . . ?
C5 C1 H1A 117.8 . . ?
N1 C2 C3 119.8(11) . . ?
N1 C2 H2A 120.1 . . ?
C3 C2 H2A 120.1 . . ?
C4 C3 C2 117.8(9) . . ?
C4 C3 H3A 121.1 . . ?
C2 C3 H3A 121.1 . . ?
C5 C4 C3 123.4(10) . . ?
C5 C4 H4A 118.3 . . ?
C3 C4 H4A 118.3 . . ?
C4 C5 C1 116.0(9) . . ?
C4 C5 C6 125.3(9) . . ?
C1 C5 C6 118.6(8) . . ?
N2 C6 C5 112.4(7) . . ?
N2 C6 H6A 109.1 . . ?
C5 C6 H6A 109.1 . . ?
N2 C6 H6B 109.1 . . ?
C5 C6 H6B 109.1 . . ?
H6A C6 H6B 107.9 . . ?
N2 C7 C7 110.9(5) . 2 ?
N2 C7 C8 113.6(7) . . ?
C7 C7 C8 111.6(5) 2 . ?
N2 C7 H7A 106.8 . . ?
C7 C7 H7A 106.8 2 . ?
C8 C7 H7A 106.8 . . ?
C9 C8 C7 113.8(6) . . ?
C9 C8 H8A 108.8 . . ?
C7 C8 H8A 108.8 . . ?
C9 C8 H8B 108.8 . . ?
C7 C8 H8B 108.8 . . ?
H8A C8 H8B 107.7 . . ?
C8 C9 C9 108.4(6) . 2 ?
C8 C9 H9A 110.0 . . ?
C9 C9 H9A 110.0 2 . ?
C8 C9 H9B 110.0 . . ?
C9 C9 H9B 110.0 2 . ?
H9A C9 H9B 108.4 . . ?
N3 C10 C14 122.7(8) . . ?
N3 C10 H10A 118.7 . . ?
C14 C10 H10A 118.7 . . ?
N3 C11 C12 124.0(10) . . ?
N3 C11 H11A 118.0 . . ?
C12 C11 H11A 118.0 . . ?
C11 C12 C13 120.3(9) . . ?
C11 C12 H12A 119.8 . . ?
C13 C12 H12A 119.8 . . ?
C14 C13 C12 116.7(8) . . ?
C14 C13 H13A 121.7 . . ?
C12 C13 H13A 121.7 . . ?
C13 C14 C10 119.1(8) . . ?
C13 C14 C15 120.5(8) . . ?
C10 C14 C15 120.4(8) . . ?
N4 C15 C14 108.4(6) . . ?
N4 C15 H15A 110.0 . . ?
C14 C15 H15A 110.0 . . ?
N4 C15 H15B 110.0 . . ?
C14 C15 H15B 110.0 . . ?
H15A C15 H15B 108.4 . . ?
N4 C16 C16 110.7(5) . 2_556 ?
N4 C16 C17 110.9(6) . . ?
C16 C16 C17 111.8(6) 2_556 . ?
N4 C16 H16A 107.7 . . ?
C16 C16 H16A 107.7 2_556 . ?
C17 C16 H16A 107.7 . . ?
C16 C17 C18 110.5(6) . . ?
C16 C17 H17A 109.6 . . ?
C18 C17 H17A 109.6 . . ?
C16 C17 H17B 109.6 . . ?
C18 C17 H17B 109.6 . . ?
H17A C17 H17B 108.1 . . ?
C17 C18 C18 110.4(6) . 2_556 ?
C17 C18 H18A 109.6 . . ?
C18 C18 H18A 109.6 2_556 . ?
C17 C18 H18B 109.6 . . ?
C18 C18 H18B 109.6 2_556 . ?
H18A C18 H18B 108.1 . . ?
O4 C19 H19A 109.5 . . ?
O4 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O4 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C2 N1 C1 118.4(8) . . ?
C2 N1 Ag1 117.2(7) . . ?
C1 N1 Ag1 123.6(5) . . ?
C6 N2 C7 113.3(6) . . ?
C6 N2 Ag2 112.3(5) . . ?
C7 N2 Ag2 111.0(5) . . ?
C10 N3 C11 117.1(8) . . ?
C10 N3 Ag2 125.4(6) . . ?
C11 N3 Ag2 116.4(7) . . ?
C16 N4 C15 112.9(6) . . ?
C16 N4 Ag1 110.7(4) . 1_556 ?
C15 N4 Ag1 115.6(5) . 1_556 ?
O3 N5 O2 137.7(10) . . ?
O3 N5 O1 113.0(10) . . ?
O2 N5 O1 109.2(9) . . ?
N5 O1 H1B 109.5 . . ?

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
O1 H1B O4 0.84 2.01 2.846(14) 171.1 .

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         1.088
_refine_diff_density_min         -1.162
_refine_diff_density_rms         0.120

#======================================

data_2
_database_code_depnum_ccdc_archive 'CCDC 861320'
#TrackingRef 'cif-LinCheng-120106.txt'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         ?
_chemical_formula_sum            'C9 H13 Cu0.50 N2.50 O2'
_chemical_formula_weight         219.99
_chemical_absolute_configuration .

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           Hexagonal
_symmetry_space_group_name_H-M   P6(1)22

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z+1/3'
'-x+y, -x, z+2/3'
'-x, -y, z+1/2'
'y, -x+y, z+5/6'
'x-y, x, z+1/6'
'y, x, -z+1/3'
'x-y, -y, -z'
'-x, -x+y, -z+2/3'
'-y, -x, -z+5/6'
'-x+y, y, -z+1/2'
'x, x-y, -z+1/6'

_cell_length_a                   13.9773(8)
_cell_length_b                   13.9773(8)
_cell_length_c                   18.263(2)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_volume                     3089.8(4)
_cell_formula_units_Z            12
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    ?
_cell_measurement_theta_min      ?
_cell_measurement_theta_max      ?

_exptl_crystal_description       block
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.69
_exptl_crystal_size_mid          0.55
_exptl_crystal_size_min          0.50
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.419
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1380
_exptl_absorpt_coefficient_mu    1.093
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.5191
_exptl_absorpt_correction_T_max  0.6109
_exptl_absorpt_process_details   'SADABS (Sheldrick, 2008)'

_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  'Bruker SMART APEX CCD'
_diffrn_measurement_method       '\f and \w scan'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            17194
_diffrn_reflns_av_R_equivalents  0.0310
_diffrn_reflns_av_sigmaI/netI    0.0209
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_k_max       17
_diffrn_reflns_limit_l_min       -22
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_theta_min         2.02
_diffrn_reflns_theta_max         26.00
_reflns_number_total             2024
_reflns_number_gt                1758
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'SMART (Bruker, 2000)'
_computing_cell_refinement       'SMART (Bruker, 2000)'
_computing_data_reduction        'SAINT (Bruker, 2000)'
_computing_structure_solution    'SHELXTL (Bruker, 2000)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics    
;
ORTEPIII (Burnett & Johnson, 1996); ORTEP-3 for Windows (Farrugia, 1997);
PLATON (Spek, 2009)
;
_computing_publication_material  'SHELXTL (Bruker, 2000)'

_refine_special_details          
;
Refinement of F^2^ against ALL reflections. The weighted R-factor wR and
goodness of fit S are based on F^2^, conventional R-factors R are based
on F, with F set to zero for negative F^2^. The threshold expression of
F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is
not relevant to the choice of reflections for refinement. R-factors based
on F^2^ 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/[\s^2^(Fo^2^)+(0.0840P)^2^+0.4579P] where P=(Fo^2^+2Fc^2^)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -0.01(3)
_refine_ls_number_reflns         2024
_refine_ls_number_parameters     130
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0515
_refine_ls_R_factor_gt           0.0421
_refine_ls_wR_factor_ref         0.1258
_refine_ls_wR_factor_gt          0.1163
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_restrained_S_all      1.118
_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
Cu1 Cu -0.67469(3) 0.0000 0.0000 0.04935(12) Uani 1 2 d S . .
N1 N -0.82884(17) -0.12692(19) 0.02955(12) 0.0529(6) Uani 1 1 d . . .
N2 N -0.97090(17) -0.42465(15) -0.09030(11) 0.0465(5) Uani 1 1 d . . .
H2B H -0.8973 -0.3969 -0.0925 0.056 Uiso 1 1 d R . .
C1 C -0.8678(2) -0.2301(2) 0.00465(15) 0.0514(6) Uani 1 1 d . . .
H1A H -0.8208 -0.2446 -0.0232 0.062 Uiso 1 1 calc R . .
C2 C -0.8968(2) -0.1081(3) 0.07200(15) 0.0590(7) Uani 1 1 d . . .
H2A H -0.8716 -0.0369 0.0895 0.071 Uiso 1 1 calc R . .
C3 C -1.0019(2) -0.1897(3) 0.09062(16) 0.0676(8) Uani 1 1 d . . .
H3A H -1.0456 -0.1742 0.1212 0.081 Uiso 1 1 calc R . .
C4 C -1.0413(2) -0.2953(3) 0.06299(15) 0.0625(8) Uani 1 1 d . . .
H4A H -1.1123 -0.3512 0.0747 0.075 Uiso 1 1 calc R . .
C5 C -0.9752(2) -0.3174(2) 0.01804(14) 0.0516(7) Uani 1 1 d . . .
C6 C -1.0169(3) -0.4314(2) -0.01564(15) 0.0620(8) Uani 1 1 d . . .
H6A H -0.9964 -0.4742 0.0158 0.074 Uiso 1 1 calc R . .
H6B H -1.0969 -0.4695 -0.0184 0.074 Uiso 1 1 calc R . .
C7 C -1.0198(2) -0.53536(19) -0.12622(14) 0.0489(6) Uani 1 1 d . . .
H7A H -1.1004 -0.5691 -0.1258 0.059 Uiso 1 1 calc R . .
C8 C -0.9892(3) -0.6139(2) -0.08628(18) 0.0688(8) Uani 1 1 d . . .
H8A H -0.9097 -0.5771 -0.0800 0.083 Uiso 1 1 calc R . .
H8B H -1.0227 -0.6308 -0.0380 0.083 Uiso 1 1 calc R . .
C9 C -1.0281(3) -0.7217(3) -0.1289(2) 0.0779(9) Uani 1 1 d . . .
H9A H -1.1077 -0.7599 -0.1346 0.094 Uiso 1 1 calc R . .
H9B H -1.0086 -0.7697 -0.1023 0.094 Uiso 1 1 calc R . .
N3 N -0.65354(19) -0.34646(19) -0.0833 0.168(4) Uani 1 2 d SD . .
O1 O -0.70106(16) -0.29894(16) -0.0833 0.1207(16) Uani 1 2 d SD . .
O2 O -0.6825(5) -0.4305(4) -0.1191(4) 0.299(5) Uani 1 1 d D . .
O1W O -0.7661(17) -0.3830(8) 0.0833 1.01(2) Uani 1 2 d S . .
H1WA H -0.7490 -0.3608 0.0394 1.211 Uiso 1 1 d R . .

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 0.04398(16) 0.0533(2) 0.0539(2) -0.00588(19) -0.00294(9) 0.02664(12)
N1 0.0453(10) 0.0558(11) 0.0528(12) -0.0066(10) 0.0031(9) 0.0217(9)
N2 0.0506(10) 0.0426(9) 0.0417(10) 0.0009(8) -0.0035(9) 0.0198(8)
C1 0.0469(11) 0.0507(13) 0.0513(13) -0.0033(11) 0.0085(11) 0.0205(9)
C2 0.0566(12) 0.0680(15) 0.0527(13) -0.0143(13) 0.0009(12) 0.0313(11)
C3 0.0498(12) 0.0876(19) 0.0598(16) -0.0155(14) 0.0077(13) 0.0300(13)
C4 0.0470(12) 0.0777(18) 0.0522(15) 0.0013(13) 0.0069(12) 0.0231(12)
C5 0.0490(12) 0.0540(12) 0.0381(11) 0.0023(10) 0.0008(9) 0.0155(11)
C6 0.0718(18) 0.0472(13) 0.0481(14) 0.0009(11) 0.0084(13) 0.0155(12)
C7 0.0499(11) 0.0423(11) 0.0555(14) 0.0012(10) -0.0044(11) 0.0239(9)
C8 0.0865(17) 0.0570(13) 0.0726(18) 0.0151(13) -0.0004(16) 0.0431(12)
C9 0.0869(18) 0.0521(13) 0.107(3) 0.0161(15) 0.0103(18) 0.0438(13)
N3 0.0858(16) 0.0858(16) 0.353(12) -0.025(5) -0.025(5) 0.058(2)
O1 0.1098(14) 0.1098(14) 0.173(4) 0.005(3) 0.005(3) 0.0774(18)
O2 0.217(5) 0.127(3) 0.562(15) 0.010(6) 0.103(8) 0.092(3)
O1W 0.256(17) 0.671(17) 1.96(6) 0.94(2) 0.000 0.128(9)

_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 2.063(2) 8 ?
Cu1 N1 2.063(2) . ?
Cu1 N2 2.145(2) 6_565 ?
Cu1 N2 2.145(2) 10_444 ?
N1 C1 1.340(4) . ?
N1 C2 1.350(4) . ?
N2 C6 1.490(3) . ?
N2 C7 1.495(3) . ?
N2 Cu1 2.145(2) 5_444 ?
N2 H2B 0.9002 . ?
C1 C5 1.404(3) . ?
C1 H1A 0.9300 . ?
C2 C3 1.378(4) . ?
C2 H2A 0.9300 . ?
C3 C4 1.387(5) . ?
C3 H3A 0.9300 . ?
C4 C5 1.383(4) . ?
C4 H4A 0.9300 . ?
C5 C6 1.525(4) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.546(4) . ?
C7 C7 1.553(5) 9_344 ?
C7 H7A 0.9800 . ?
C8 C9 1.534(5) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C9 1.539(7) 9_344 ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
N3 O1 1.150(5) . ?
N3 O2 1.222(5) 10_444 ?
N3 O2 1.222(5) . ?
O1W H1WA 0.8503 . ?

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 104.20(15) 8 . ?
N1 Cu1 N2 120.23(8) 8 6_565 ?
N1 Cu1 N2 114.08(9) . 6_565 ?
N1 Cu1 N2 114.08(9) 8 10_444 ?
N1 Cu1 N2 120.23(8) . 10_444 ?
N2 Cu1 N2 84.20(11) 6_565 10_444 ?
C1 N1 C2 117.2(2) . . ?
C1 N1 Cu1 121.59(18) . . ?
C2 N1 Cu1 121.11(19) . . ?
C6 N2 C7 112.12(19) . . ?
C6 N2 Cu1 114.85(19) . 5_444 ?
C7 N2 Cu1 104.38(14) . 5_444 ?
C6 N2 H2B 115.6 . . ?
C7 N2 H2B 105.0 . . ?
Cu1 N2 H2B 103.7 5_444 . ?
N1 C1 C5 124.0(3) . . ?
N1 C1 H1A 118.0 . . ?
C5 C1 H1A 118.0 . . ?
N1 C2 C3 122.9(3) . . ?
N1 C2 H2A 118.5 . . ?
C3 C2 H2A 118.5 . . ?
C2 C3 C4 118.9(3) . . ?
C2 C3 H3A 120.5 . . ?
C4 C3 H3A 120.5 . . ?
C5 C4 C3 120.0(3) . . ?
C5 C4 H4A 120.0 . . ?
C3 C4 H4A 120.0 . . ?
C4 C5 C1 116.9(2) . . ?
C4 C5 C6 121.6(2) . . ?
C1 C5 C6 121.5(2) . . ?
N2 C6 C5 112.0(2) . . ?
N2 C6 H6A 109.2 . . ?
C5 C6 H6A 109.2 . . ?
N2 C6 H6B 109.2 . . ?
C5 C6 H6B 109.2 . . ?
H6A C6 H6B 107.9 . . ?
N2 C7 C8 112.5(2) . . ?
N2 C7 C7 107.17(16) . 9_344 ?
C8 C7 C7 112.01(18) . 9_344 ?
N2 C7 H7A 108.4 . . ?
C8 C7 H7A 108.4 . . ?
C7 C7 H7A 108.4 9_344 . ?
C9 C8 C7 111.7(3) . . ?
C9 C8 H8A 109.3 . . ?
C7 C8 H8A 109.3 . . ?
C9 C8 H8B 109.3 . . ?
C7 C8 H8B 109.3 . . ?
H8A C8 H8B 107.9 . . ?
C8 C9 C9 108.6(2) . 9_344 ?
C8 C9 H9A 110.0 . . ?
C9 C9 H9A 110.0 9_344 . ?
C8 C9 H9B 110.0 . . ?
C9 C9 H9B 110.0 9_344 . ?
H9A C9 H9B 108.3 . . ?
O1 N3 O2 123.1(4) . 10_444 ?
O1 N3 O2 123.1(4) . . ?
O2 N3 O2 113.9(8) 10_444 . ?

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 132.4(3) 8 . . . ?
N2 Cu1 N1 C1 -94.6(2) 6_565 . . . ?
N2 Cu1 N1 C1 3.0(3) 10_444 . . . ?
N1 Cu1 N1 C2 -44.3(2) 8 . . . ?
N2 Cu1 N1 C2 88.7(2) 6_565 . . . ?
N2 Cu1 N1 C2 -173.7(2) 10_444 . . . ?
C2 N1 C1 C5 2.3(4) . . . . ?
Cu1 N1 C1 C5 -174.6(2) . . . . ?
C1 N1 C2 C3 0.6(4) . . . . ?
Cu1 N1 C2 C3 177.4(2) . . . . ?
N1 C2 C3 C4 -2.0(5) . . . . ?
C2 C3 C4 C5 0.5(5) . . . . ?
C3 C4 C5 C1 2.0(4) . . . . ?
C3 C4 C5 C6 -177.8(3) . . . . ?
N1 C1 C5 C4 -3.6(4) . . . . ?
N1 C1 C5 C6 176.3(3) . . . . ?
C7 N2 C6 C5 -174.6(2) . . . . ?
Cu1 N2 C6 C5 -55.7(3) 5_444 . . . ?
C4 C5 C6 N2 145.2(3) . . . . ?
C1 C5 C6 N2 -34.6(4) . . . . ?
C6 N2 C7 C8 -65.4(3) . . . . ?
Cu1 N2 C7 C8 169.70(18) 5_444 . . . ?
C6 N2 C7 C7 171.1(2) . . . 9_344 ?
Cu1 N2 C7 C7 46.2(2) 5_444 . . 9_344 ?
N2 C7 C8 C9 -173.1(2) . . . . ?
C7 C7 C8 C9 -52.3(3) 9_344 . . . ?
C7 C8 C9 C9 60.3(4) . . . 9_344 ?

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
N2 H2B O1 0.90 2.38 3.271(3) 169.7 .
O1W H1WA O1 0.85 2.38 3.225(5) 179.9 .

_diffrn_measured_fraction_theta_max 0.990
_diffrn_reflns_theta_full        26.00
_diffrn_measured_fraction_theta_full 0.990
_refine_diff_density_max         0.455
_refine_diff_density_min         -0.310
_refine_diff_density_rms         0.062

#===============================END