# Supplementary Material (ESI) for CrystEngComm
# This journal is (c) The Royal Society of Chemistry 2010
data_global
_journal_name_full CrystEngComm
_journal_coden_Cambridge 1350
_publ_contact_author_name 'Cai, Yue-Peng'
_publ_contact_author_email ypcaizsu@yahoo.com.cn
_publ_section_title
;
Construction of three high-dimensional supramolecular networks
from temperature-driven conformational isomers
;
loop_
_publ_author_name
'Hua-Cai Fang'
'Yingying Ge'
'Hong-Yang Jia'
'Shan-Shan Li'
'Feng Sun'
;
Li-Guo Zhang
;
'Yue-Peng Cai'
# Attachment '- 784672(1).cif'
data_1
_database_code_depnum_ccdc_archive 'CCDC 784672'
#TrackingRef '- 784672(1).cif'
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
?
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety 'C10 H15 N9 Zn '
_chemical_formula_sum 'C10 H15 N9 Zn '
_chemical_formula_weight 326.70
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'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting triclinic
_symmetry_space_group_name_H-M 'P -1'
_symmetry_space_group_name_Hall '-P 1'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
_cell_length_a 7.2594(12)
_cell_length_b 9.3403(16)
_cell_length_c 11.835(2)
_cell_angle_alpha 71.216(2)
_cell_angle_beta 76.045(2)
_cell_angle_gamma 70.261(2)
_cell_volume 707.2(2)
_cell_formula_units_Z 2
_cell_measurement_temperature 296(2)
_cell_measurement_reflns_used 1795
_cell_measurement_theta_min 2.40
_cell_measurement_theta_max 25.18
_exptl_crystal_description block
_exptl_crystal_colour colorless
_exptl_crystal_size_max 0.27
_exptl_crystal_size_mid 0.18
_exptl_crystal_size_min 0.11
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.534
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 336
_exptl_absorpt_coefficient_mu 1.742
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_correction_T_min 0.693
_exptl_absorpt_correction_T_max 0.826
_exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)'
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 296(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-II CCD'
_diffrn_measurement_method '\f and \w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number 3676
_diffrn_reflns_av_R_equivalents 0.0200
_diffrn_reflns_av_sigmaI/netI 0.0368
_diffrn_reflns_limit_h_min -8
_diffrn_reflns_limit_h_max 8
_diffrn_reflns_limit_k_min -11
_diffrn_reflns_limit_k_max 11
_diffrn_reflns_limit_l_min -14
_diffrn_reflns_limit_l_max 12
_diffrn_reflns_theta_min 1.84
_diffrn_reflns_theta_max 25.19
_reflns_number_total 2555
_reflns_number_gt 2206
_reflns_threshold_expression >2sigma(I)
_computing_data_collection 'Bruker APEX2'
_computing_cell_refinement 'Bruker SAINT'
_computing_data_reduction 'Bruker SAINT'
_computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics 'SHELXTL-XP (Bruker, 2004)'
_computing_publication_material SHELXL-97
_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^)+(0.0352P)^2^+0.0000P] 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_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns 2499
_refine_ls_number_parameters 184
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0344
_refine_ls_R_factor_gt 0.0295
_refine_ls_wR_factor_ref 0.0734
_refine_ls_wR_factor_gt 0.0709
_refine_ls_goodness_of_fit_ref 1.099
_refine_ls_restrained_S_all 1.099
_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
C1 C 0.7403(6) 0.6745(4) 0.3566(3) 0.0507(9) Uani 1 1 d . . .
H1 H 0.6046 0.7029 0.3563 0.061 Uiso 1 1 calc R . .
C2 C 0.8146(7) 0.7618(5) 0.4002(4) 0.0576(10) Uani 1 1 d . . .
H2 H 0.7304 0.8469 0.4287 0.069 Uiso 1 1 calc R . .
C3 C 1.0137(7) 0.7203(5) 0.4003(4) 0.0578(10) Uani 1 1 d . . .
H3 H 1.0671 0.7779 0.4281 0.069 Uiso 1 1 calc R . .
C4 C 1.1354(6) 0.5920(5) 0.3590(3) 0.0510(9) Uani 1 1 d . . .
H4 H 1.2713 0.5612 0.3592 0.061 Uiso 1 1 calc R . .
C5 C 1.0510(5) 0.5114(4) 0.3176(3) 0.0418(8) Uani 1 1 d . . .
C6 C 1.1677(5) 0.3717(4) 0.2729(3) 0.0451(8) Uani 1 1 d . . .
H6 H 1.3028 0.3309 0.2762 0.054 Uiso 1 1 calc R . .
C7 C 1.1835(5) 0.1716(4) 0.1821(4) 0.0491(9) Uani 1 1 d . . .
H7A H 1.2761 0.0947 0.2345 0.059 Uiso 1 1 calc R . .
H7B H 1.2565 0.2031 0.1026 0.059 Uiso 1 1 calc R . .
C8 C 1.0287(5) 0.1011(4) 0.1751(4) 0.0489(9) Uani 1 1 d . . .
H8A H 1.0874 0.0270 0.1259 0.059 Uiso 1 1 calc R . .
H8B H 0.9831 0.0437 0.2555 0.059 Uiso 1 1 calc R . .
C9 C 0.9127(6) 0.2976(5) -0.0054(3) 0.0592(10) Uani 1 1 d . . .
H9A H 1.0139 0.3469 -0.0144 0.089 Uiso 1 1 calc R . .
H9B H 0.7982 0.3756 -0.0363 0.089 Uiso 1 1 calc R . .
H9C H 0.9610 0.2187 -0.0494 0.089 Uiso 1 1 calc R . .
C10 C 0.6973(6) 0.1544(5) 0.1361(4) 0.0618(11) Uani 1 1 d . . .
H10A H 0.7400 0.0779 0.0901 0.093 Uiso 1 1 calc R . .
H10B H 0.5841 0.2363 0.1069 0.093 Uiso 1 1 calc R . .
H10C H 0.6627 0.1043 0.2196 0.093 Uiso 1 1 calc R . .
N1 N 0.8557(4) 0.5516(3) 0.3149(3) 0.0427(7) Uani 1 1 d . . .
N2 N 1.0816(4) 0.3090(3) 0.2303(2) 0.0393(6) Uani 1 1 d . . .
N3 N 0.8590(4) 0.2234(3) 0.1231(3) 0.0408(6) Uani 1 1 d . . .
N4 N 0.6054(5) 0.5681(4) 0.1224(3) 0.0648(10) Uani 1 1 d . . .
N5 N 0.5371(6) 0.6975(4) 0.1311(4) 0.0753(8) Uani 1 1 d . . .
N6 N 0.4689(6) 0.8257(4) 0.1327(4) 0.0753(8) Uani 1 1 d . . .
N7 N 0.6169(5) 0.2926(5) 0.3775(3) 0.0654(10) Uani 1 1 d U . .
N8 N 0.6688(5) 0.1772(4) 0.4542(3) 0.0513(8) Uani 1 1 d U . .
N9 N 0.7092(7) 0.0665(5) 0.5317(4) 0.0843(12) Uani 1 1 d . . .
Zn1 Zn 0.77624(5) 0.39614(4) 0.23295(4) 0.03990(18) 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
C1 0.050(2) 0.053(2) 0.048(2) -0.0170(17) -0.0115(17) -0.0066(17)
C2 0.075(3) 0.047(2) 0.052(2) -0.0149(18) -0.013(2) -0.015(2)
C3 0.080(3) 0.058(2) 0.050(2) -0.0118(19) -0.015(2) -0.036(2)
C4 0.051(2) 0.061(2) 0.048(2) -0.0104(18) -0.0125(17) -0.0247(19)
C5 0.0392(19) 0.049(2) 0.0363(18) -0.0043(15) -0.0094(14) -0.0155(15)
C6 0.0311(17) 0.054(2) 0.047(2) -0.0122(17) -0.0079(15) -0.0074(15)
C7 0.0328(18) 0.049(2) 0.062(2) -0.0213(18) -0.0090(16) 0.0014(15)
C8 0.045(2) 0.0346(18) 0.062(2) -0.0132(16) -0.0091(17) -0.0029(15)
C9 0.063(3) 0.063(2) 0.048(2) -0.0178(19) -0.0060(19) -0.012(2)
C10 0.050(2) 0.067(3) 0.082(3) -0.031(2) -0.010(2) -0.023(2)
N1 0.0397(16) 0.0477(16) 0.0445(17) -0.0171(13) -0.0116(13) -0.0089(13)
N2 0.0333(15) 0.0404(15) 0.0431(16) -0.0105(12) -0.0079(12) -0.0079(12)
N3 0.0357(15) 0.0399(15) 0.0476(17) -0.0137(13) -0.0066(12) -0.0092(12)
N4 0.067(2) 0.051(2) 0.078(2) -0.0217(18) -0.0400(19) 0.0069(17)
N5 0.086(2) 0.0550(15) 0.0743(17) -0.0227(14) -0.0345(15) 0.0143(14)
N6 0.086(2) 0.0550(15) 0.0743(17) -0.0227(14) -0.0345(15) 0.0143(14)
N7 0.0458(19) 0.078(2) 0.059(2) -0.0079(19) 0.0024(16) -0.0170(18)
N8 0.0474(18) 0.067(2) 0.050(2) -0.0281(18) -0.0022(15) -0.0215(16)
N9 0.102(3) 0.073(3) 0.073(3) -0.009(2) -0.018(2) -0.024(2)
Zn1 0.0290(2) 0.0409(3) 0.0476(3) -0.01291(18) -0.00812(16) -0.00420(16)
_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
C1 N1 1.333(5) . ?
C1 C2 1.387(6) . ?
C1 H1 0.9300 . ?
C2 C3 1.364(6) . ?
C2 H2 0.9300 . ?
C3 C4 1.382(6) . ?
C3 H3 0.9300 . ?
C4 C5 1.369(5) . ?
C4 H4 0.9300 . ?
C5 N1 1.344(4) . ?
C5 C6 1.477(5) . ?
C6 N2 1.256(4) . ?
C6 H6 0.9300 . ?
C7 N2 1.465(4) . ?
C7 C8 1.511(5) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 N3 1.471(4) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 N3 1.471(5) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 N3 1.475(5) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
N1 Zn1 2.264(3) . ?
N2 Zn1 2.083(3) . ?
N3 Zn1 2.230(3) . ?
N4 N5 1.169(5) . ?
N4 Zn1 1.978(3) . ?
N5 N6 1.136(5) . ?
N7 N8 1.178(5) . ?
N7 Zn1 1.984(3) . ?
N8 N9 1.145(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
N1 C1 C2 122.6(4) . . ?
N1 C1 H1 118.7 . . ?
C2 C1 H1 118.7 . . ?
C3 C2 C1 118.7(4) . . ?
C3 C2 H2 120.7 . . ?
C1 C2 H2 120.7 . . ?
C2 C3 C4 119.6(4) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C5 C4 C3 118.3(4) . . ?
C5 C4 H4 120.8 . . ?
C3 C4 H4 120.8 . . ?
N1 C5 C4 123.1(3) . . ?
N1 C5 C6 114.4(3) . . ?
C4 C5 C6 122.6(3) . . ?
N2 C6 C5 118.9(3) . . ?
N2 C6 H6 120.5 . . ?
C5 C6 H6 120.5 . . ?
N2 C7 C8 107.8(3) . . ?
N2 C7 H7A 110.1 . . ?
C8 C7 H7A 110.1 . . ?
N2 C7 H7B 110.1 . . ?
C8 C7 H7B 110.1 . . ?
H7A C7 H7B 108.5 . . ?
N3 C8 C7 111.5(3) . . ?
N3 C8 H8A 109.3 . . ?
C7 C8 H8A 109.3 . . ?
N3 C8 H8B 109.3 . . ?
C7 C8 H8B 109.3 . . ?
H8A C8 H8B 108.0 . . ?
N3 C9 H9A 109.5 . . ?
N3 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N3 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N3 C10 H10A 109.5 . . ?
N3 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
N3 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C1 N1 C5 117.7(3) . . ?
C1 N1 Zn1 129.9(3) . . ?
C5 N1 Zn1 112.4(2) . . ?
C6 N2 C7 123.4(3) . . ?
C6 N2 Zn1 119.5(2) . . ?
C7 N2 Zn1 117.1(2) . . ?
C9 N3 C8 111.9(3) . . ?
C9 N3 C10 108.9(3) . . ?
C8 N3 C10 110.1(3) . . ?
C9 N3 Zn1 111.1(2) . . ?
C8 N3 Zn1 103.1(2) . . ?
C10 N3 Zn1 111.8(2) . . ?
N5 N4 Zn1 124.7(3) . . ?
N6 N5 N4 176.0(5) . . ?
N8 N7 Zn1 129.4(3) . . ?
N9 N8 N7 176.4(4) . . ?
N4 Zn1 N7 111.42(16) . . ?
N4 Zn1 N2 133.47(14) . . ?
N7 Zn1 N2 115.08(13) . . ?
N4 Zn1 N3 95.57(12) . . ?
N7 Zn1 N3 100.38(14) . . ?
N2 Zn1 N3 77.94(10) . . ?
N4 Zn1 N1 96.79(12) . . ?
N7 Zn1 N1 99.00(14) . . ?
N2 Zn1 N1 74.76(10) . . ?
N3 Zn1 N1 151.32(11) . . ?
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 C1 C2 C3 0.1(6) . . . . ?
C1 C2 C3 C4 -0.9(6) . . . . ?
C2 C3 C4 C5 0.7(6) . . . . ?
C3 C4 C5 N1 0.3(6) . . . . ?
C3 C4 C5 C6 -179.3(3) . . . . ?
N1 C5 C6 N2 4.2(5) . . . . ?
C4 C5 C6 N2 -176.2(3) . . . . ?
N2 C7 C8 N3 45.2(4) . . . . ?
C2 C1 N1 C5 0.9(5) . . . . ?
C2 C1 N1 Zn1 -177.4(3) . . . . ?
C4 C5 N1 C1 -1.1(5) . . . . ?
C6 C5 N1 C1 178.5(3) . . . . ?
C4 C5 N1 Zn1 177.5(3) . . . . ?
C6 C5 N1 Zn1 -2.9(4) . . . . ?
C5 C6 N2 C7 179.2(3) . . . . ?
C5 C6 N2 Zn1 -3.3(4) . . . . ?
C8 C7 N2 C6 163.1(3) . . . . ?
C8 C7 N2 Zn1 -14.5(4) . . . . ?
C7 C8 N3 C9 68.2(4) . . . . ?
C7 C8 N3 C10 -170.7(3) . . . . ?
C7 C8 N3 Zn1 -51.2(3) . . . . ?
Zn1 N4 N5 N6 163(8) . . . . ?
Zn1 N7 N8 N9 176(7) . . . . ?
N5 N4 Zn1 N7 85.1(5) . . . . ?
N5 N4 Zn1 N2 -92.8(5) . . . . ?
N5 N4 Zn1 N3 -171.5(4) . . . . ?
N5 N4 Zn1 N1 -17.4(5) . . . . ?
N8 N7 Zn1 N4 171.1(4) . . . . ?
N8 N7 Zn1 N2 -10.6(5) . . . . ?
N8 N7 Zn1 N3 70.9(4) . . . . ?
N8 N7 Zn1 N1 -87.9(4) . . . . ?
C6 N2 Zn1 N4 86.1(3) . . . . ?
C7 N2 Zn1 N4 -96.2(3) . . . . ?
C6 N2 Zn1 N7 -91.7(3) . . . . ?
C7 N2 Zn1 N7 85.9(3) . . . . ?
C6 N2 Zn1 N3 172.3(3) . . . . ?
C7 N2 Zn1 N3 -10.0(2) . . . . ?
C6 N2 Zn1 N1 1.2(3) . . . . ?
C7 N2 Zn1 N1 178.9(3) . . . . ?
C9 N3 Zn1 N4 45.4(3) . . . . ?
C8 N3 Zn1 N4 165.4(2) . . . . ?
C10 N3 Zn1 N4 -76.4(3) . . . . ?
C9 N3 Zn1 N7 158.5(3) . . . . ?
C8 N3 Zn1 N7 -81.6(2) . . . . ?
C10 N3 Zn1 N7 36.6(3) . . . . ?
C9 N3 Zn1 N2 -87.9(2) . . . . ?
C8 N3 Zn1 N2 32.1(2) . . . . ?
C10 N3 Zn1 N2 150.3(3) . . . . ?
C9 N3 Zn1 N1 -69.8(3) . . . . ?
C8 N3 Zn1 N1 50.2(3) . . . . ?
C10 N3 Zn1 N1 168.4(3) . . . . ?
C1 N1 Zn1 N4 46.2(3) . . . . ?
C5 N1 Zn1 N4 -132.2(3) . . . . ?
C1 N1 Zn1 N7 -66.9(3) . . . . ?
C5 N1 Zn1 N7 114.8(2) . . . . ?
C1 N1 Zn1 N2 179.5(3) . . . . ?
C5 N1 Zn1 N2 1.1(2) . . . . ?
C1 N1 Zn1 N3 161.1(3) . . . . ?
C5 N1 Zn1 N3 -17.2(4) . . . . ?
_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full 25.19
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max 1.220
_refine_diff_density_min -1.192
_refine_diff_density_rms 0.065
# Attachment '- 784673(2).cif'
data_2
_database_code_depnum_ccdc_archive 'CCDC 784673'
#TrackingRef '- 784673(2).cif'
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
?
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety 'C10 H15 N9 Zn '
_chemical_formula_sum 'C10 H15 N9 Zn '
_chemical_formula_weight 326.70
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'
Zn Zn 0.2839 1.4301 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
_symmetry_cell_setting triclinic
_symmetry_space_group_name_H-M 'P -1'
_symmetry_space_group_name_Hall '-P 1'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
_cell_length_a 8.3950(12)
_cell_length_b 9.5035(13)
_cell_length_c 10.2058(14)
_cell_angle_alpha 71.530(2)
_cell_angle_beta 84.594(2)
_cell_angle_gamma 72.106(2)
_cell_volume 734.93(18)
_cell_formula_units_Z 2
_cell_measurement_temperature 296(2)
_cell_measurement_reflns_used 1278
_cell_measurement_theta_min 2.36
_cell_measurement_theta_max 22.45
_exptl_crystal_description block
_exptl_crystal_colour colorless
_exptl_crystal_size_max 0.24
_exptl_crystal_size_mid 0.18
_exptl_crystal_size_min 0.16
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.476
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 336
_exptl_absorpt_coefficient_mu 1.677
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_correction_T_min 0.693
_exptl_absorpt_correction_T_max 0.826
_exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)'
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 296(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-II CCD'
_diffrn_measurement_method '\f and \w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number 3726
_diffrn_reflns_av_R_equivalents 0.0167
_diffrn_reflns_av_sigmaI/netI 0.0354
_diffrn_reflns_limit_h_min -10
_diffrn_reflns_limit_h_max 10
_diffrn_reflns_limit_k_min -6
_diffrn_reflns_limit_k_max 11
_diffrn_reflns_limit_l_min -12
_diffrn_reflns_limit_l_max 12
_diffrn_reflns_theta_min 2.10
_diffrn_reflns_theta_max 25.20
_reflns_number_total 2560
_reflns_number_gt 2028
_reflns_threshold_expression >2sigma(I)
_computing_data_collection 'Bruker APEX2'
_computing_cell_refinement 'Bruker SAINT'
_computing_data_reduction 'Bruker SAINT'
_computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics 'SHELXTL-XP (Bruker, 2004)'
_computing_publication_material SHELXL-97
_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^)+(0.0511P)^2^+0.0781P] 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_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns 2560
_refine_ls_number_parameters 184
_refine_ls_number_restraints 0
_refine_ls_R_factor_all 0.0526
_refine_ls_R_factor_gt 0.0396
_refine_ls_wR_factor_ref 0.0985
_refine_ls_wR_factor_gt 0.0915
_refine_ls_goodness_of_fit_ref 1.042
_refine_ls_restrained_S_all 1.042
_refine_ls_shift/su_max 0.033
_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
N4 N 0.1629(6) 0.5619(4) 0.0538(4) 0.0843(12) Uani 1 1 d . . .
N5 N 0.1282(5) 0.6601(4) 0.1086(4) 0.0741(10) Uani 1 1 d . . .
N6 N 0.0910(6) 0.7604(5) 0.1560(6) 0.1001(14) Uani 1 1 d . . .
N7 N 0.4707(5) 0.2836(6) 0.2251(4) 0.0955(10) Uani 1 1 d U . .
N8 N 0.5454(6) 0.2178(6) 0.3187(5) 0.0955(10) Uani 1 1 d U . .
N9A N 0.633(4) 0.185(3) 0.416(3) 0.136(6) Uani 0.50 1 d PU . .
N9B N 0.624(4) 0.118(3) 0.400(3) 0.136(6) Uani 0.50 1 d PU . .
C1 C 0.4580(6) 0.3409(7) -0.1410(5) 0.0838(14) Uani 1 1 d . . .
H1 H 0.4891 0.4219 -0.1290 0.101 Uiso 1 1 calc R . .
C2 C 0.5184(7) 0.2903(8) -0.2546(6) 0.1031(19) Uani 1 1 d . . .
H2 H 0.5892 0.3359 -0.3177 0.124 Uiso 1 1 calc R . .
C3 C 0.4712(7) 0.1717(9) -0.2712(6) 0.103(2) Uani 1 1 d . . .
H3 H 0.5092 0.1364 -0.3470 0.124 Uiso 1 1 calc R . .
C4 C 0.3687(6) 0.1051(7) -0.1775(5) 0.0853(15) Uani 1 1 d . . .
H4 H 0.3368 0.0235 -0.1875 0.102 Uiso 1 1 calc R . .
C5 C 0.3136(5) 0.1615(5) -0.0676(4) 0.0636(11) Uani 1 1 d . . .
C6 C 0.2019(6) 0.0998(5) 0.0369(5) 0.0670(11) Uani 1 1 d . . .
H6 H 0.1670 0.0170 0.0338 0.080 Uiso 1 1 calc R . .
C7 C 0.0368(7) 0.1118(6) 0.2383(6) 0.0907(15) Uani 1 1 d . . .
H7A H 0.0541 0.0011 0.2601 0.109 Uiso 1 1 calc R . .
H7B H -0.0777 0.1659 0.2068 0.109 Uiso 1 1 calc R . .
C8 C 0.0692(8) 0.1494(6) 0.3622(6) 0.1018(18) Uani 1 1 d . . .
H8A H -0.0201 0.1366 0.4284 0.122 Uiso 1 1 calc R . .
H8B H 0.1731 0.0766 0.4051 0.122 Uiso 1 1 calc R . .
C9 C -0.0844(6) 0.4217(6) 0.3004(6) 0.0914(15) Uani 1 1 d . . .
H9A H -0.1277 0.4220 0.2165 0.137 Uiso 1 1 calc R . .
H9B H -0.0746 0.5227 0.2900 0.137 Uiso 1 1 calc R . .
H9C H -0.1592 0.3959 0.3751 0.137 Uiso 1 1 calc R . .
C10 C 0.1543(8) 0.3195(9) 0.4502(6) 0.127(3) Uani 1 1 d . . .
H10A H 0.1675 0.4212 0.4287 0.190 Uiso 1 1 calc R . .
H10B H 0.2617 0.2430 0.4712 0.190 Uiso 1 1 calc R . .
H10C H 0.0819 0.3025 0.5285 0.190 Uiso 1 1 calc R . .
N1 N 0.3580(4) 0.2784(4) -0.0497(4) 0.0631(8) Uani 1 1 d . . .
N2 N 0.1538(4) 0.1616(4) 0.1315(4) 0.0646(9) Uani 1 1 d . . .
N3 N 0.0803(5) 0.3068(4) 0.3302(4) 0.0713(9) Uani 1 1 d . . .
Zn1 Zn 0.24815(6) 0.33510(5) 0.14108(5) 0.0590(2) 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
N4 0.124(3) 0.047(2) 0.076(2) -0.0183(19) 0.001(2) -0.016(2)
N5 0.081(2) 0.0433(19) 0.099(3) -0.018(2) -0.014(2) -0.0193(18)
N6 0.101(3) 0.067(3) 0.150(4) -0.055(3) -0.024(3) -0.020(2)
N7 0.083(2) 0.123(3) 0.073(2) -0.0162(19) -0.0143(16) -0.031(2)
N8 0.083(2) 0.123(3) 0.073(2) -0.0162(19) -0.0143(16) -0.031(2)
N9A 0.103(5) 0.207(17) 0.096(7) -0.036(10) -0.028(4) -0.044(11)
N9B 0.103(5) 0.207(17) 0.096(7) -0.036(10) -0.028(4) -0.044(11)
C1 0.068(3) 0.095(4) 0.084(3) -0.023(3) 0.003(3) -0.023(3)
C2 0.067(3) 0.140(6) 0.083(4) -0.021(4) 0.005(3) -0.018(3)
C3 0.075(3) 0.141(6) 0.076(4) -0.052(4) -0.009(3) 0.014(4)
C4 0.076(3) 0.095(4) 0.083(3) -0.052(3) -0.013(3) 0.006(3)
C5 0.060(2) 0.051(2) 0.075(3) -0.029(2) -0.019(2) 0.0061(19)
C6 0.081(3) 0.046(2) 0.082(3) -0.027(2) -0.008(2) -0.018(2)
C7 0.117(4) 0.069(3) 0.096(4) -0.023(3) 0.028(3) -0.051(3)
C8 0.125(5) 0.070(3) 0.088(4) -0.006(3) 0.021(3) -0.022(3)
C9 0.087(3) 0.080(3) 0.088(3) -0.021(3) 0.001(3) -0.004(3)
C10 0.115(5) 0.183(7) 0.073(4) -0.060(4) -0.018(3) -0.005(5)
N1 0.0593(19) 0.060(2) 0.067(2) -0.0203(17) -0.0057(17) -0.0106(17)
N2 0.082(2) 0.0448(18) 0.069(2) -0.0179(16) 0.0011(18) -0.0210(17)
N3 0.089(3) 0.060(2) 0.059(2) -0.0185(17) -0.0046(18) -0.0123(19)
Zn1 0.0733(3) 0.0430(3) 0.0629(3) -0.0177(2) -0.0106(2) -0.0154(2)
_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
N4 N5 1.184(5) . ?
N4 Zn1 1.977(4) . ?
N5 N6 1.149(5) . ?
N7 N8 1.091(6) . ?
N7 Zn1 1.985(4) . ?
N8 N9B 1.11(3) . ?
N8 N9A 1.20(2) . ?
N9A N9B 0.73(3) . ?
C1 N1 1.316(6) . ?
C1 C2 1.387(7) . ?
C1 H1 0.9300 . ?
C2 C3 1.366(9) . ?
C2 H2 0.9300 . ?
C3 C4 1.361(9) . ?
C3 H3 0.9300 . ?
C4 C5 1.375(6) . ?
C4 H4 0.9300 . ?
C5 N1 1.343(5) . ?
C5 C6 1.454(6) . ?
C6 N2 1.258(5) . ?
C6 H6 0.9300 . ?
C7 N2 1.461(6) . ?
C7 C8 1.487(8) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 N3 1.457(6) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 N3 1.462(6) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 N3 1.478(6) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
N1 Zn1 2.226(3) . ?
N2 Zn1 2.067(3) . ?
N3 Zn1 2.274(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
N5 N4 Zn1 127.6(3) . . ?
N6 N5 N4 176.7(5) . . ?
N8 N7 Zn1 143.7(4) . . ?
N7 N8 N9B 160.4(11) . . ?
N7 N8 N9A 161.9(13) . . ?
N9B N8 N9A 36.7(17) . . ?
N9B N9A N8 66(3) . . ?
N9A N9B N8 78(4) . . ?
N1 C1 C2 122.3(5) . . ?
N1 C1 H1 118.8 . . ?
C2 C1 H1 118.8 . . ?
C3 C2 C1 118.2(5) . . ?
C3 C2 H2 120.9 . . ?
C1 C2 H2 120.9 . . ?
C4 C3 C2 120.3(5) . . ?
C4 C3 H3 119.8 . . ?
C2 C3 H3 119.8 . . ?
C3 C4 C5 118.2(5) . . ?
C3 C4 H4 120.9 . . ?
C5 C4 H4 120.9 . . ?
N1 C5 C4 122.4(5) . . ?
N1 C5 C6 115.2(3) . . ?
C4 C5 C6 122.4(4) . . ?
N2 C6 C5 118.0(4) . . ?
N2 C6 H6 121.0 . . ?
C5 C6 H6 121.0 . . ?
N2 C7 C8 107.1(4) . . ?
N2 C7 H7A 110.3 . . ?
C8 C7 H7A 110.3 . . ?
N2 C7 H7B 110.3 . . ?
C8 C7 H7B 110.3 . . ?
H7A C7 H7B 108.6 . . ?
N3 C8 C7 113.0(4) . . ?
N3 C8 H8A 109.0 . . ?
C7 C8 H8A 109.0 . . ?
N3 C8 H8B 109.0 . . ?
C7 C8 H8B 109.0 . . ?
H8A C8 H8B 107.8 . . ?
N3 C9 H9A 109.5 . . ?
N3 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N3 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N3 C10 H10A 109.5 . . ?
N3 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
N3 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C1 N1 C5 118.6(4) . . ?
C1 N1 Zn1 129.3(3) . . ?
C5 N1 Zn1 112.1(3) . . ?
C6 N2 C7 122.2(4) . . ?
C6 N2 Zn1 119.3(3) . . ?
C7 N2 Zn1 118.5(3) . . ?
C8 N3 C9 111.5(4) . . ?
C8 N3 C10 108.6(5) . . ?
C9 N3 C10 109.1(4) . . ?
C8 N3 Zn1 104.3(3) . . ?
C9 N3 Zn1 111.0(3) . . ?
C10 N3 Zn1 112.2(4) . . ?
N4 Zn1 N7 109.4(2) . . ?
N4 Zn1 N2 129.33(17) . . ?
N7 Zn1 N2 120.74(18) . . ?
N4 Zn1 N1 96.28(15) . . ?
N7 Zn1 N1 93.16(16) . . ?
N2 Zn1 N1 75.12(13) . . ?
N4 Zn1 N3 100.01(15) . . ?
N7 Zn1 N3 101.95(16) . . ?
N2 Zn1 N3 77.48(14) . . ?
N1 Zn1 N3 152.57(14) . . ?
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
Zn1 N4 N5 N6 -168(9) . . . . ?
Zn1 N7 N8 N9B 77(5) . . . . ?
Zn1 N7 N8 N9A -128(5) . . . . ?
N7 N8 N9A N9B -166(2) . . . . ?
N7 N8 N9B N9A 167(2) . . . . ?
N1 C1 C2 C3 0.2(8) . . . . ?
C1 C2 C3 C4 -0.6(8) . . . . ?
C2 C3 C4 C5 0.7(8) . . . . ?
C3 C4 C5 N1 -0.4(7) . . . . ?
C3 C4 C5 C6 179.1(4) . . . . ?
N1 C5 C6 N2 1.6(6) . . . . ?
C4 C5 C6 N2 -177.9(4) . . . . ?
N2 C7 C8 N3 47.7(6) . . . . ?
C2 C1 N1 C5 0.1(7) . . . . ?
C2 C1 N1 Zn1 178.9(4) . . . . ?
C4 C5 N1 C1 0.0(6) . . . . ?
C6 C5 N1 C1 -179.5(4) . . . . ?
C4 C5 N1 Zn1 -179.0(3) . . . . ?
C6 C5 N1 Zn1 1.5(4) . . . . ?
C5 C6 N2 C7 177.7(4) . . . . ?
C5 C6 N2 Zn1 -4.2(5) . . . . ?
C8 C7 N2 C6 153.6(4) . . . . ?
C8 C7 N2 Zn1 -24.5(5) . . . . ?
C7 C8 N3 C9 74.0(6) . . . . ?
C7 C8 N3 C10 -165.7(5) . . . . ?
C7 C8 N3 Zn1 -45.8(5) . . . . ?
N5 N4 Zn1 N7 -63.7(5) . . . . ?
N5 N4 Zn1 N2 124.8(4) . . . . ?
N5 N4 Zn1 N1 -159.3(5) . . . . ?
N5 N4 Zn1 N3 42.8(5) . . . . ?
N8 N7 Zn1 N4 132.0(8) . . . . ?
N8 N7 Zn1 N2 -55.7(9) . . . . ?
N8 N7 Zn1 N1 -130.2(8) . . . . ?
N8 N7 Zn1 N3 26.7(9) . . . . ?
C6 N2 Zn1 N4 89.6(4) . . . . ?
C7 N2 Zn1 N4 -92.2(4) . . . . ?
C6 N2 Zn1 N7 -81.0(4) . . . . ?
C7 N2 Zn1 N7 97.2(4) . . . . ?
C6 N2 Zn1 N1 3.7(3) . . . . ?
C7 N2 Zn1 N1 -178.1(4) . . . . ?
C6 N2 Zn1 N3 -177.6(4) . . . . ?
C7 N2 Zn1 N3 0.6(3) . . . . ?
C1 N1 Zn1 N4 49.4(4) . . . . ?
C5 N1 Zn1 N4 -131.7(3) . . . . ?
C1 N1 Zn1 N7 -60.5(4) . . . . ?
C5 N1 Zn1 N7 118.4(3) . . . . ?
C1 N1 Zn1 N2 178.5(4) . . . . ?
C5 N1 Zn1 N2 -2.6(3) . . . . ?
C1 N1 Zn1 N3 175.7(4) . . . . ?
C5 N1 Zn1 N3 -5.4(4) . . . . ?
C8 N3 Zn1 N4 152.0(3) . . . . ?
C9 N3 Zn1 N4 31.8(3) . . . . ?
C10 N3 Zn1 N4 -90.7(4) . . . . ?
C8 N3 Zn1 N7 -95.6(4) . . . . ?
C9 N3 Zn1 N7 144.2(3) . . . . ?
C10 N3 Zn1 N7 21.8(4) . . . . ?
C8 N3 Zn1 N2 23.7(3) . . . . ?
C9 N3 Zn1 N2 -96.6(3) . . . . ?
C10 N3 Zn1 N2 141.0(4) . . . . ?
C8 N3 Zn1 N1 26.4(5) . . . . ?
C9 N3 Zn1 N1 -93.8(4) . . . . ?
C10 N3 Zn1 N1 143.8(4) . . . . ?
_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_theta_full 25.20
_diffrn_measured_fraction_theta_full 0.997
_refine_diff_density_max 0.806
_refine_diff_density_min -0.770
_refine_diff_density_rms 0.056
# Attachment '- 784674(3).cif'
data_3
_database_code_depnum_ccdc_archive 'CCDC 784674'
#TrackingRef '- 784674(3).cif'
_audit_creation_method SHELXL-97
_chemical_name_systematic
;
?
;
_chemical_name_common ?
_chemical_melting_point ?
_chemical_formula_moiety 'C10 H15 N9 Zn '
_chemical_formula_sum 'C10 H15 N9 Zn '
_chemical_formula_weight 326.70
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'
Zn Zn 0.2839 1.4301 '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/c'
_symmetry_space_group_name_Hall '-P 2ybc'
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
_cell_length_a 9.8594(17)
_cell_length_b 11.0993(18)
_cell_length_c 13.426(2)
_cell_angle_alpha 90.00
_cell_angle_beta 93.789(2)
_cell_angle_gamma 90.00
_cell_volume 1466.0(4)
_cell_formula_units_Z 4
_cell_measurement_temperature 296(2)
_cell_measurement_reflns_used 2297
_cell_measurement_theta_min 2.77
_cell_measurement_theta_max 23.94
_exptl_crystal_description block
_exptl_crystal_colour colorless
_exptl_crystal_size_max 0.25
_exptl_crystal_size_mid 0.19
_exptl_crystal_size_min 0.17
_exptl_crystal_density_meas ?
_exptl_crystal_density_diffrn 1.480
_exptl_crystal_density_method 'not measured'
_exptl_crystal_F_000 672
_exptl_absorpt_coefficient_mu 1.681
_exptl_absorpt_correction_type multi-scan
_exptl_absorpt_correction_T_min 0.688
_exptl_absorpt_correction_T_max 0.751
_exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)'
_exptl_special_details
;
?
;
_diffrn_ambient_temperature 296(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-II CCD'
_diffrn_measurement_method '\f and \w scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number 6624
_diffrn_reflns_av_R_equivalents 0.0253
_diffrn_reflns_av_sigmaI/netI 0.0303
_diffrn_reflns_limit_h_min -11
_diffrn_reflns_limit_h_max 11
_diffrn_reflns_limit_k_min -8
_diffrn_reflns_limit_k_max 13
_diffrn_reflns_limit_l_min -15
_diffrn_reflns_limit_l_max 16
_diffrn_reflns_theta_min 2.38
_diffrn_reflns_theta_max 25.20
_reflns_number_total 2643
_reflns_number_gt 1879
_reflns_threshold_expression >2sigma(I)
_computing_data_collection 'Bruker APEX2'
_computing_cell_refinement 'Bruker SAINT'
_computing_data_reduction 'Bruker SAINT'
_computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)'
_computing_molecular_graphics 'SHELXTL-XP (Bruker, 2004)'
_computing_publication_material SHELXL-97
_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^)+(0.0958P)^2^+0.0000P] 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_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_number_reflns 2442
_refine_ls_number_parameters 178
_refine_ls_number_restraints 138
_refine_ls_R_factor_all 0.0635
_refine_ls_R_factor_gt 0.0490
_refine_ls_wR_factor_ref 0.1393
_refine_ls_wR_factor_gt 0.1268
_refine_ls_goodness_of_fit_ref 1.025
_refine_ls_restrained_S_all 1.028
_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
C1 C 0.7839(4) 1.1980(4) 0.6233(3) 0.0587(10) Uani 1 1 d U . .
H1 H 0.7503 1.1885 0.6860 0.070 Uiso 1 1 calc R . .
C2 C 0.8300(5) 1.3116(5) 0.5970(4) 0.0688(11) Uani 1 1 d U . .
H2 H 0.8271 1.3766 0.6405 0.083 Uiso 1 1 calc R . .
C3 C 0.8802(5) 1.3239(5) 0.5044(4) 0.0711(12) Uani 1 1 d U . .
H3 H 0.9108 1.3986 0.4839 0.085 Uiso 1 1 calc R . .
C4 C 0.8850(5) 1.2267(5) 0.4424(4) 0.0679(12) Uani 1 1 d U . .
H4 H 0.9202 1.2341 0.3802 0.082 Uiso 1 1 calc R . .
C5 C 0.8362(4) 1.1161(4) 0.4740(3) 0.0557(9) Uani 1 1 d U . .
C6 C 0.8303(4) 1.0074(5) 0.4129(3) 0.0616(11) Uani 1 1 d U . .
H6 H 0.8655 1.0066 0.3503 0.074 Uiso 1 1 calc R . .
C7 C 0.7610(6) 0.8016(5) 0.3910(4) 0.0801(14) Uani 1 1 d U . .
H7A H 0.8397 0.7884 0.3527 0.096 Uiso 1 1 calc R . .
H7B H 0.6809 0.8053 0.3451 0.096 Uiso 1 1 calc R . .
C8 C 0.7475(5) 0.7014(5) 0.4638(4) 0.0773(9) Uani 1 1 d U . .
H8A H 0.7204 0.6285 0.4280 0.093 Uiso 1 1 calc R . .
H8B H 0.8349 0.6867 0.4991 0.093 Uiso 1 1 calc R . .
C9 C 0.6781(12) 0.6392(6) 0.6099(7) 0.158(4) Uani 1 1 d U . .
H9A H 0.6494 0.6652 0.6733 0.237 Uiso 1 1 calc R . .
H9B H 0.7745 0.6256 0.6149 0.237 Uiso 1 1 calc R . .
H9C H 0.6321 0.5658 0.5906 0.237 Uiso 1 1 calc R . .
C10 C 0.5067(8) 0.7284(7) 0.5045(7) 0.137(3) Uani 1 1 d U . .
H10A H 0.4767 0.8091 0.4895 0.205 Uiso 1 1 calc R . .
H10B H 0.4550 0.6958 0.5564 0.205 Uiso 1 1 calc R . .
H10C H 0.4936 0.6794 0.4458 0.205 Uiso 1 1 calc R . .
N1 N 0.7852(3) 1.1029(3) 0.5639(2) 0.0509(8) Uani 1 1 d . . .
N2 N 0.7763(4) 0.9143(3) 0.4471(3) 0.0594(9) Uani 1 1 d . . .
N3 N 0.6460(4) 0.7298(4) 0.5368(4) 0.0773(9) Uani 1 1 d . . .
N4 N 0.8450(4) 0.8734(4) 0.6985(3) 0.0714(10) Uani 1 1 d . . .
N5 N 0.8983(4) 0.9471(3) 0.7503(3) 0.0592(9) Uani 1 1 d . . .
N6 N 0.9586(5) 1.0144(5) 0.8010(4) 0.0942(14) Uani 1 1 d . . .
N7 N 0.5330(4) 0.9791(4) 0.6359(4) 0.0774(12) Uani 1 1 d . . .
N8 N 0.4620(4) 0.9326(4) 0.6898(3) 0.0684(10) Uani 1 1 d . . .
N9 N 0.3848(6) 0.8924(6) 0.7421(4) 0.1067(17) Uani 1 1 d . . .
Zn1 Zn 0.70538(4) 0.91748(4) 0.58861(3) 0.0494(2) 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
C1 0.062(2) 0.057(2) 0.058(2) 0.0034(19) 0.0093(18) 0.0010(19)
C2 0.064(2) 0.062(3) 0.081(3) -0.002(2) 0.009(2) -0.004(2)
C3 0.064(2) 0.062(3) 0.089(3) 0.015(2) 0.015(2) -0.010(2)
C4 0.057(2) 0.076(3) 0.072(3) 0.022(2) 0.021(2) -0.001(2)
C5 0.054(2) 0.062(2) 0.051(2) 0.0052(18) 0.0099(16) 0.0023(18)
C6 0.059(2) 0.073(3) 0.055(2) 0.005(2) 0.0149(18) 0.009(2)
C7 0.100(3) 0.074(3) 0.067(3) -0.028(2) 0.018(2) 0.008(3)
C8 0.0769(19) 0.0638(18) 0.090(2) -0.0128(16) -0.0025(15) 0.0064(15)
C9 0.239(9) 0.055(4) 0.165(7) 0.005(4) -0.110(7) 0.016(5)
C10 0.092(4) 0.096(5) 0.217(9) -0.041(5) -0.029(5) -0.008(4)
N1 0.0526(17) 0.0503(18) 0.0507(18) 0.0027(14) 0.0101(14) 0.0067(14)
N2 0.070(2) 0.062(2) 0.0479(18) -0.0054(16) 0.0131(15) 0.0155(17)
N3 0.0769(19) 0.0638(18) 0.090(2) -0.0128(16) -0.0025(15) 0.0064(15)
N4 0.088(3) 0.063(2) 0.062(2) 0.003(2) -0.007(2) 0.005(2)
N5 0.068(2) 0.062(2) 0.0472(19) 0.0013(18) 0.0023(17) 0.0170(19)
N6 0.095(3) 0.088(3) 0.095(3) -0.022(3) -0.026(3) 0.019(3)
N7 0.073(2) 0.056(2) 0.108(3) 0.006(2) 0.038(2) 0.0057(19)
N8 0.070(2) 0.072(3) 0.066(2) 0.0059(19) 0.024(2) 0.0064(19)
N9 0.100(4) 0.136(4) 0.087(4) 0.024(3) 0.032(3) -0.013(3)
Zn1 0.0559(3) 0.0466(3) 0.0464(3) -0.00078(17) 0.00990(19) 0.00212(19)
_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
C1 N1 1.323(6) . ?
C1 C2 1.394(7) . ?
C1 H1 0.9300 . ?
C2 C3 1.376(7) . ?
C2 H2 0.9300 . ?
C3 C4 1.364(7) . ?
C3 H3 0.9300 . ?
C4 C5 1.395(6) . ?
C4 H4 0.9300 . ?
C5 N1 1.346(5) . ?
C5 C6 1.458(7) . ?
C6 N2 1.262(6) . ?
C6 H6 0.9300 . ?
C7 N2 1.463(6) . ?
C7 C8 1.492(8) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 N3 1.480(7) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 N3 1.426(8) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 N3 1.413(9) . ?
C10 H10A 0.9600 . ?
C10 H10B 0.9600 . ?
C10 H10C 0.9600 . ?
N1 Zn1 2.236(3) . ?
N2 Zn1 2.067(4) . ?
N3 Zn1 2.261(4) . ?
N4 N5 1.175(6) . ?
N4 Zn1 2.011(4) . ?
N5 N6 1.149(6) . ?
N7 N8 1.160(5) . ?
N7 Zn1 1.976(4) . ?
N8 N9 1.159(6) . ?
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 C1 C2 123.5(4) . . ?
N1 C1 H1 118.2 . . ?
C2 C1 H1 118.2 . . ?
C3 C2 C1 117.5(5) . . ?
C3 C2 H2 121.3 . . ?
C1 C2 H2 121.3 . . ?
C4 C3 C2 120.1(4) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C3 C4 C5 119.0(4) . . ?
C3 C4 H4 120.5 . . ?
C5 C4 H4 120.5 . . ?
N1 C5 C4 121.7(4) . . ?
N1 C5 C6 114.3(4) . . ?
C4 C5 C6 124.0(4) . . ?
N2 C6 C5 118.3(4) . . ?
N2 C6 H6 120.8 . . ?
C5 C6 H6 120.8 . . ?
N2 C7 C8 108.1(4) . . ?
N2 C7 H7A 110.1 . . ?
C8 C7 H7A 110.1 . . ?
N2 C7 H7B 110.1 . . ?
C8 C7 H7B 110.1 . . ?
H7A C7 H7B 108.4 . . ?
N3 C8 C7 111.6(4) . . ?
N3 C8 H8A 109.3 . . ?
C7 C8 H8A 109.3 . . ?
N3 C8 H8B 109.3 . . ?
C7 C8 H8B 109.3 . . ?
H8A C8 H8B 108.0 . . ?
N3 C9 H9A 109.5 . . ?
N3 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N3 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
N3 C10 H10A 109.5 . . ?
N3 C10 H10B 109.5 . . ?
H10A C10 H10B 109.5 . . ?
N3 C10 H10C 109.5 . . ?
H10A C10 H10C 109.5 . . ?
H10B C10 H10C 109.5 . . ?
C1 N1 C5 118.2(4) . . ?
C1 N1 Zn1 128.8(3) . . ?
C5 N1 Zn1 112.9(3) . . ?
C6 N2 C7 122.9(4) . . ?
C6 N2 Zn1 119.8(3) . . ?
C7 N2 Zn1 117.3(3) . . ?
C10 N3 C9 111.7(7) . . ?
C10 N3 C8 118.7(6) . . ?
C9 N3 C8 100.1(6) . . ?
C10 N3 Zn1 109.3(4) . . ?
C9 N3 Zn1 113.4(4) . . ?
C8 N3 Zn1 103.1(3) . . ?
N5 N4 Zn1 121.5(3) . . ?
N6 N5 N4 175.2(5) . . ?
N8 N7 Zn1 127.8(4) . . ?
N9 N8 N7 175.3(5) . . ?
N7 Zn1 N4 114.20(19) . . ?
N7 Zn1 N2 130.70(18) . . ?
N4 Zn1 N2 114.41(16) . . ?
N7 Zn1 N1 92.74(15) . . ?
N4 Zn1 N1 95.85(16) . . ?
N2 Zn1 N1 74.67(13) . . ?
N7 Zn1 N3 101.95(17) . . ?
N4 Zn1 N3 98.78(17) . . ?
N2 Zn1 N3 78.35(16) . . ?
N1 Zn1 N3 152.74(15) . . ?
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 C1 C2 C3 -0.4(7) . . . . ?
C1 C2 C3 C4 -0.8(7) . . . . ?
C2 C3 C4 C5 1.1(7) . . . . ?
C3 C4 C5 N1 -0.3(7) . . . . ?
C3 C4 C5 C6 177.2(4) . . . . ?
N1 C5 C6 N2 1.9(6) . . . . ?
C4 C5 C6 N2 -175.7(4) . . . . ?
N2 C7 C8 N3 48.5(6) . . . . ?
C2 C1 N1 C5 1.2(6) . . . . ?
C2 C1 N1 Zn1 -176.1(3) . . . . ?
C4 C5 N1 C1 -0.9(6) . . . . ?
C6 C5 N1 C1 -178.6(3) . . . . ?
C4 C5 N1 Zn1 176.9(3) . . . . ?
C6 C5 N1 Zn1 -0.8(4) . . . . ?
C5 C6 N2 C7 177.9(4) . . . . ?
C5 C6 N2 Zn1 -2.1(6) . . . . ?
C8 C7 N2 C6 157.6(4) . . . . ?
C8 C7 N2 Zn1 -22.4(5) . . . . ?
C7 C8 N3 C10 72.7(7) . . . . ?
C7 C8 N3 C9 -165.5(5) . . . . ?
C7 C8 N3 Zn1 -48.4(5) . . . . ?
Zn1 N4 N5 N6 -144(6) . . . . ?
Zn1 N7 N8 N9 -172(7) . . . . ?
N8 N7 Zn1 N4 -55.8(6) . . . . ?
N8 N7 Zn1 N2 134.5(5) . . . . ?
N8 N7 Zn1 N1 -153.4(5) . . . . ?
N8 N7 Zn1 N3 49.7(5) . . . . ?
N5 N4 Zn1 N7 -68.5(5) . . . . ?
N5 N4 Zn1 N2 103.0(4) . . . . ?
N5 N4 Zn1 N1 27.2(4) . . . . ?
N5 N4 Zn1 N3 -175.9(4) . . . . ?
C6 N2 Zn1 N7 81.4(4) . . . . ?
C7 N2 Zn1 N7 -98.6(4) . . . . ?
C6 N2 Zn1 N4 -88.3(4) . . . . ?
C7 N2 Zn1 N4 91.7(4) . . . . ?
C6 N2 Zn1 N1 1.3(3) . . . . ?
C7 N2 Zn1 N1 -178.8(4) . . . . ?
C6 N2 Zn1 N3 177.3(4) . . . . ?
C7 N2 Zn1 N3 -2.8(4) . . . . ?
C1 N1 Zn1 N7 45.8(4) . . . . ?
C5 N1 Zn1 N7 -131.7(3) . . . . ?
C1 N1 Zn1 N4 -68.9(4) . . . . ?
C5 N1 Zn1 N4 113.6(3) . . . . ?
C1 N1 Zn1 N2 177.3(4) . . . . ?
C5 N1 Zn1 N2 -0.1(3) . . . . ?
C1 N1 Zn1 N3 168.8(3) . . . . ?
C5 N1 Zn1 N3 -8.7(5) . . . . ?
C10 N3 Zn1 N7 29.2(6) . . . . ?
C9 N3 Zn1 N7 -96.2(7) . . . . ?
C8 N3 Zn1 N7 156.4(3) . . . . ?
C10 N3 Zn1 N4 146.4(5) . . . . ?
C9 N3 Zn1 N4 20.9(7) . . . . ?
C8 N3 Zn1 N4 -86.4(3) . . . . ?
C10 N3 Zn1 N2 -100.4(6) . . . . ?
C9 N3 Zn1 N2 134.2(7) . . . . ?
C8 N3 Zn1 N2 26.9(3) . . . . ?
C10 N3 Zn1 N1 -92.0(6) . . . . ?
C9 N3 Zn1 N1 142.6(6) . . . . ?
C8 N3 Zn1 N1 35.3(5) . . . . ?
_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full 25.20
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max 0.828
_refine_diff_density_min -0.878
_refine_diff_density_rms 0.076