# 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
_journal_year                    ?
_journal_volume                  ?
_journal_page_first              ?
_publ_contact_author_name        'Yaoting Fan'
_publ_contact_author_address     
;
Department of chemistry
Zhengzhou University
Zhengzhou 450001
China
;
_publ_contact_author_email       yt.fan@zzu.edu.cn

_publ_section_title              
;
A novel dodecanuclear cadmium(II) macrocycles with 3D framework:
syntheses, structures and properties
;
loop_
_publ_author_name
'Yaoting Fan'
'Wenjuan Chu'
'Benlai Wu'
'Mingsheng Tang'
'Hongwei Hou'

# END

data_Htmb_2
_database_code_depnum_ccdc_archive 'CCDC 829379'

#TrackingRef '- data.cif.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C11 H12 Cd Cl N5 O'
_chemical_formula_sum            'C11 H12 Cd Cl N5 O'
_chemical_formula_weight         378.11

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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Cd Cd -0.8075 1.2024 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_symmetry_cell_setting           trigonal
_symmetry_space_group_name_H-M   ' R-3'
_symmetry_space_group_name_Hall  '-R3 '

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

_cell_length_a                   22.496(3)
_cell_length_b                   22.496(3)
_cell_length_c                   14.870(3)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_volume                     6516.7(19)
_cell_formula_units_Z            18
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    17178
_cell_measurement_theta_min      1.8104
_cell_measurement_theta_max      31.0625

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.734
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             3348
_exptl_absorpt_coefficient_mu    1.691
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.8482
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   '(Otwinowski & Minor, 1997)'

_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  Rigaku
_diffrn_measurement_method       \w
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         2
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  150
_diffrn_standards_decay_%        none
_diffrn_reflns_number            17178
_diffrn_reflns_av_R_equivalents  0.0423
_diffrn_reflns_av_sigmaI/netI    0.0277
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_k_min       -26
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.50
_diffrn_reflns_theta_max         24.99
_reflns_number_total             2553
_reflns_number_gt                2465
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku/MSC Inc., 2006)'
_computing_cell_refinement       'CrystalClear (Rigaku/MSC Inc., 2006)'
_computing_data_reduction        'CrystalClear (Rigaku/MSC Inc., 2006)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXS-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXS (Sheldrick, 2008)'
_computing_publication_material  'SHELXS (Sheldrick, 2008)'

_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^)+(0.0896P)^2^+8.9069P] 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    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_refine_ls_number_reflns         2553
_refine_ls_number_parameters     177
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0444
_refine_ls_R_factor_gt           0.0418
_refine_ls_wR_factor_ref         0.1365
_refine_ls_wR_factor_gt          0.1338
_refine_ls_goodness_of_fit_ref   1.090
_refine_ls_restrained_S_all      1.090
_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
Cd1 Cd 0.388250(19) 0.263120(19) 0.64700(2) 0.0334(2) Uani 1 1 d . . .
N1 N 0.4673(3) 0.2335(3) 0.9271(4) 0.0593(15) Uani 1 1 d . . .
N2 N 0.4257(3) 0.2552(2) 0.8015(3) 0.0447(11) Uani 1 1 d . . .
N3 N 0.4031(2) 0.2732(2) 0.8759(3) 0.0378(10) Uani 1 1 d . . .
N4 N 0.3894(2) 0.3549(2) 0.7177(3) 0.0342(9) Uani 1 1 d . . .
N5 N 0.3987(2) 0.4230(2) 0.8362(3) 0.0337(9) Uani 1 1 d . . .
C1 C 0.4639(4) 0.2321(3) 0.8368(5) 0.0560(16) Uani 1 1 d . . .
H1 H 0.4869 0.2159 0.8017 0.067 Uiso 1 1 calc R . .
C2 C 0.4276(4) 0.2596(3) 0.9491(4) 0.0537(16) Uani 1 1 d . . .
H2 H 0.4184 0.2672 1.0076 0.064 Uiso 1 1 calc R . .
C3 C 0.3555(3) 0.2993(3) 0.8680(3) 0.0379(12) Uani 1 1 d . . .
H3A H 0.3476 0.3122 0.9272 0.046 Uiso 1 1 calc R . .
H3B H 0.3119 0.2631 0.8453 0.046 Uiso 1 1 calc R . .
C4 C 0.3821(3) 0.3602(2) 0.8065(3) 0.0317(11) Uani 1 1 d . . .
C5 C 0.4131(3) 0.4212(3) 0.6862(3) 0.0351(11) Uani 1 1 d . . .
C6 C 0.4301(3) 0.4478(3) 0.5992(4) 0.0478(14) Uani 1 1 d . . .
H6 H 0.4262 0.4199 0.5507 0.057 Uiso 1 1 calc R . .
C7 C 0.4526(4) 0.5163(3) 0.5877(4) 0.0553(16) Uani 1 1 d . . .
H7 H 0.4645 0.5353 0.5304 0.066 Uiso 1 1 calc R . .
C8 C 0.4580(4) 0.5578(3) 0.6601(4) 0.0585(18) Uani 1 1 d . . .
H8 H 0.4730 0.6040 0.6500 0.070 Uiso 1 1 calc R . .
C9 C 0.4418(3) 0.5325(3) 0.7457(4) 0.0491(14) Uani 1 1 d . . .
H9 H 0.4459 0.5607 0.7939 0.059 Uiso 1 1 calc R . .
C10 C 0.4190(3) 0.4634(2) 0.7582(4) 0.0355(12) Uani 1 1 d . . .
C11 C 0.5572(5) 0.3220(6) 0.5825(10) 0.164(7) Uani 1 1 d . . .
H11A H 0.5391 0.2738 0.5734 0.245 Uiso 1 1 calc R . .
H11B H 0.5942 0.3388 0.6251 0.245 Uiso 1 1 calc R . .
H11C H 0.5740 0.3458 0.5264 0.245 Uiso 1 1 calc R . .
Cl1 Cl 0.40519(7) 0.15604(7) 0.63066(9) 0.0402(3) Uani 1 1 d . . .
H1W H 0.524(3) 0.367(2) 0.651(4) 0.06(2) Uiso 1 1 d D . .
O1 O 0.5059(2) 0.3333(2) 0.6152(3) 0.0613(12) Uani 1 1 d 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
Cd1 0.0388(3) 0.0347(3) 0.0292(3) -0.00474(14) -0.00482(14) 0.02036(18)
N1 0.081(4) 0.052(3) 0.055(3) 0.000(2) -0.017(3) 0.041(3)
N2 0.058(3) 0.047(3) 0.041(3) -0.008(2) -0.007(2) 0.036(3)
N3 0.052(3) 0.030(2) 0.030(2) -0.0034(17) -0.006(2) 0.020(2)
N4 0.043(2) 0.030(2) 0.028(2) -0.0038(17) 0.0008(18) 0.017(2)
N5 0.045(2) 0.036(2) 0.024(2) 0.0009(17) 0.0012(18) 0.023(2)
C1 0.070(4) 0.051(4) 0.063(4) -0.006(3) -0.009(3) 0.041(3)
C2 0.080(5) 0.039(3) 0.043(3) 0.000(3) -0.015(3) 0.030(3)
C3 0.051(3) 0.036(3) 0.030(3) -0.002(2) 0.002(2) 0.024(3)
C4 0.035(3) 0.028(3) 0.028(3) -0.003(2) 0.003(2) 0.013(2)
C5 0.038(3) 0.039(3) 0.030(3) 0.003(2) 0.004(2) 0.020(2)
C6 0.055(4) 0.050(3) 0.035(3) 0.003(2) 0.006(3) 0.023(3)
C7 0.074(4) 0.044(3) 0.037(3) 0.012(3) 0.011(3) 0.022(3)
C8 0.085(5) 0.039(3) 0.045(4) 0.013(3) 0.008(3) 0.026(3)
C9 0.063(4) 0.038(3) 0.045(3) 0.000(3) 0.007(3) 0.024(3)
C10 0.041(3) 0.032(3) 0.029(3) 0.000(2) 0.001(2) 0.015(2)
C11 0.065(6) 0.162(12) 0.216(15) -0.093(11) 0.021(8) 0.021(7)
Cl1 0.0415(7) 0.0377(7) 0.0450(7) -0.0024(5) -0.0001(6) 0.0224(6)
O1 0.040(2) 0.063(3) 0.062(3) -0.022(2) 0.004(2) 0.011(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
Cd1 N5 2.271(4) 9_554 ?
Cd1 N4 2.306(4) . ?
Cd1 O1 2.354(4) . ?
Cd1 N2 2.484(5) . ?
Cd1 Cl1 2.6315(14) . ?
Cd1 Cl1 2.6534(14) 13_556 ?
N1 C2 1.330(9) . ?
N1 C1 1.343(8) . ?
N2 C1 1.314(8) . ?
N2 N3 1.361(6) . ?
N3 C2 1.323(7) . ?
N3 C3 1.460(7) . ?
N4 C4 1.342(6) . ?
N4 C5 1.390(7) . ?
N5 C4 1.343(6) . ?
N5 C10 1.402(6) . ?
N5 Cd1 2.271(4) 5 ?
C1 H1 0.9300 . ?
C2 H2 0.9300 . ?
C3 C4 1.501(7) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C5 C6 1.396(7) . ?
C5 C10 1.393(7) . ?
C6 C7 1.372(8) . ?
C6 H6 0.9300 . ?
C7 C8 1.390(9) . ?
C7 H7 0.9300 . ?
C8 C9 1.368(8) . ?
C8 H8 0.9300 . ?
C9 C10 1.385(7) . ?
C9 H9 0.9300 . ?
C11 O1 1.388(11) . ?
C11 H11A 0.9600 . ?
C11 H11B 0.9600 . ?
C11 H11C 0.9600 . ?
Cl1 Cd1 2.6534(14) 13_556 ?
O1 H1W 0.851(10) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
N5 Cd1 N4 104.82(15) 9_554 . ?
N5 Cd1 O1 92.56(16) 9_554 . ?
N4 Cd1 O1 89.19(16) . . ?
N5 Cd1 N2 176.81(15) 9_554 . ?
N4 Cd1 N2 77.88(15) . . ?
O1 Cd1 N2 85.73(17) . . ?
N5 Cd1 Cl1 98.21(11) 9_554 . ?
N4 Cd1 Cl1 156.91(11) . . ?
O1 Cd1 Cl1 88.07(13) . . ?
N2 Cd1 Cl1 79.05(11) . . ?
N5 Cd1 Cl1 95.04(11) 9_554 13_556 ?
N4 Cd1 Cl1 92.05(11) . 13_556 ?
O1 Cd1 Cl1 171.71(13) . 13_556 ?
N2 Cd1 Cl1 86.52(12) . 13_556 ?
Cl1 Cd1 Cl1 87.57(4) . 13_556 ?
C2 N1 C1 102.3(5) . . ?
C1 N2 N3 102.0(5) . . ?
C1 N2 Cd1 135.3(4) . . ?
N3 N2 Cd1 122.7(3) . . ?
C2 N3 N2 109.8(5) . . ?
C2 N3 C3 129.2(5) . . ?
N2 N3 C3 120.8(4) . . ?
C4 N4 C5 103.6(4) . . ?
C4 N4 Cd1 125.5(3) . . ?
C5 N4 Cd1 129.3(3) . . ?
C4 N5 C10 103.9(4) . . ?
C4 N5 Cd1 128.2(3) . 5 ?
C10 N5 Cd1 127.6(3) . 5 ?
N2 C1 N1 115.5(6) . . ?
N2 C1 H1 122.2 . . ?
N1 C1 H1 122.2 . . ?
N1 C2 N3 110.4(6) . . ?
N1 C2 H2 124.8 . . ?
N3 C2 H2 124.8 . . ?
N3 C3 C4 112.2(4) . . ?
N3 C3 H3A 109.2 . . ?
C4 C3 H3A 109.2 . . ?
N3 C3 H3B 109.2 . . ?
C4 C3 H3B 109.2 . . ?
H3A C3 H3B 107.9 . . ?
N5 C4 N4 115.7(4) . . ?
N5 C4 C3 122.3(4) . . ?
N4 C4 C3 121.9(4) . . ?
N4 C5 C6 130.4(5) . . ?
N4 C5 C10 109.1(4) . . ?
C6 C5 C10 120.5(5) . . ?
C7 C6 C5 117.8(6) . . ?
C7 C6 H6 121.1 . . ?
C5 C6 H6 121.1 . . ?
C6 C7 C8 121.1(6) . . ?
C6 C7 H7 119.4 . . ?
C8 C7 H7 119.4 . . ?
C9 C8 C7 121.8(6) . . ?
C9 C8 H8 119.1 . . ?
C7 C8 H8 119.1 . . ?
C8 C9 C10 117.6(6) . . ?
C8 C9 H9 121.2 . . ?
C10 C9 H9 121.2 . . ?
C9 C10 N5 131.0(5) . . ?
C9 C10 C5 121.3(5) . . ?
N5 C10 C5 107.7(4) . . ?
O1 C11 H11A 109.5 . . ?
O1 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
O1 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
Cd1 Cl1 Cd1 92.43(4) . 13_556 ?
C11 O1 Cd1 135.0(6) . . ?
C11 O1 H1W 109(5) . . ?
Cd1 O1 H1W 110(5) . . ?

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
N4 Cd1 N2 C1 -151.3(6) . . . . ?
O1 Cd1 N2 C1 -61.2(6) . . . . ?
Cl1 Cd1 N2 C1 27.7(6) . . . . ?
Cl1 Cd1 N2 C1 115.9(6) 13_556 . . . ?
N4 Cd1 N2 N3 33.6(4) . . . . ?
O1 Cd1 N2 N3 123.7(4) . . . . ?
Cl1 Cd1 N2 N3 -147.4(4) . . . . ?
Cl1 Cd1 N2 N3 -59.2(4) 13_556 . . . ?
C1 N2 N3 C2 -0.6(6) . . . . ?
Cd1 N2 N3 C2 175.9(4) . . . . ?
C1 N2 N3 C3 -177.3(5) . . . . ?
Cd1 N2 N3 C3 -0.8(6) . . . . ?
N5 Cd1 N4 C4 156.5(4) 9_554 . . . ?
O1 Cd1 N4 C4 -111.1(4) . . . . ?
N2 Cd1 N4 C4 -25.3(4) . . . . ?
Cl1 Cd1 N4 C4 -27.9(6) . . . . ?
Cl1 Cd1 N4 C4 60.7(4) 13_556 . . . ?
N5 Cd1 N4 C5 -40.6(5) 9_554 . . . ?
O1 Cd1 N4 C5 51.8(4) . . . . ?
N2 Cd1 N4 C5 137.6(5) . . . . ?
Cl1 Cd1 N4 C5 135.0(4) . . . . ?
Cl1 Cd1 N4 C5 -136.4(4) 13_556 . . . ?
N3 N2 C1 N1 0.2(7) . . . . ?
Cd1 N2 C1 N1 -175.5(4) . . . . ?
C2 N1 C1 N2 0.2(8) . . . . ?
C1 N1 C2 N3 -0.6(7) . . . . ?
N2 N3 C2 N1 0.8(7) . . . . ?
C3 N3 C2 N1 177.1(5) . . . . ?
C2 N3 C3 C4 129.1(6) . . . . ?
N2 N3 C3 C4 -55.0(6) . . . . ?
C10 N5 C4 N4 0.3(6) . . . . ?
Cd1 N5 C4 N4 -174.2(3) 5 . . . ?
C10 N5 C4 C3 -178.5(5) . . . . ?
Cd1 N5 C4 C3 7.0(7) 5 . . . ?
C5 N4 C4 N5 -0.1(6) . . . . ?
Cd1 N4 C4 N5 166.3(3) . . . . ?
C5 N4 C4 C3 178.6(5) . . . . ?
Cd1 N4 C4 C3 -14.9(7) . . . . ?
N3 C3 C4 N5 -114.1(5) . . . . ?
N3 C3 C4 N4 67.2(6) . . . . ?
C4 N4 C5 C6 -179.9(6) . . . . ?
Cd1 N4 C5 C6 14.4(8) . . . . ?
C4 N4 C5 C10 -0.1(6) . . . . ?
Cd1 N4 C5 C10 -165.8(4) . . . . ?
N4 C5 C6 C7 -179.9(6) . . . . ?
C10 C5 C6 C7 0.3(9) . . . . ?
C5 C6 C7 C8 -0.4(10) . . . . ?
C6 C7 C8 C9 0.6(12) . . . . ?
C7 C8 C9 C10 -0.6(11) . . . . ?
C8 C9 C10 N5 -180.0(6) . . . . ?
C8 C9 C10 C5 0.4(9) . . . . ?
C4 N5 C10 C9 -179.9(6) . . . . ?
Cd1 N5 C10 C9 -5.4(9) 5 . . . ?
C4 N5 C10 C5 -0.3(6) . . . . ?
Cd1 N5 C10 C5 174.2(3) 5 . . . ?
N4 C5 C10 C9 179.9(5) . . . . ?
C6 C5 C10 C9 -0.3(9) . . . . ?
N4 C5 C10 N5 0.2(6) . . . . ?
C6 C5 C10 N5 -179.9(5) . . . . ?
N5 Cd1 Cl1 Cd1 -94.74(11) 9_554 . . 13_556 ?
N4 Cd1 Cl1 Cd1 89.5(3) . . . 13_556 ?
O1 Cd1 Cl1 Cd1 172.94(12) . . . 13_556 ?
N2 Cd1 Cl1 Cd1 86.92(12) . . . 13_556 ?
Cl1 Cd1 Cl1 Cd1 0.0 13_556 . . 13_556 ?
N5 Cd1 O1 C11 -85.6(11) 9_554 . . . ?
N4 Cd1 O1 C11 169.6(11) . . . . ?
N2 Cd1 O1 C11 91.7(11) . . . . ?
Cl1 Cd1 O1 C11 12.5(11) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        24.99
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.740
_refine_diff_density_min         -0.420
_refine_diff_density_rms         0.081

# END


data_Htmb
_database_code_depnum_ccdc_archive 'CCDC 869705'
#TrackingRef '- data.cif.cif'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C10 H8 N5'
_chemical_formula_sum            'C10 H8 N5'
_chemical_formula_weight         198.21

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'

_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_H-M   Pbca
_symmetry_space_group_name_Hall  '-P 2ac 2ab'

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

_cell_length_a                   6.4648(13)
_cell_length_b                   9.841(2)
_cell_length_c                   30.508(6)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1941.0(7)
_cell_formula_units_Z            8
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    17519
_cell_measurement_theta_min      2.6704
_cell_measurement_theta_max      27.8884

_exptl_crystal_description       needle
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.20
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.357
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             824
_exptl_absorpt_coefficient_mu    0.090
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_correction_T_min  0.9823
_exptl_absorpt_correction_T_max  0.9911
_exptl_absorpt_process_details   '(Otwinowski & Minor, 1997)'

_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  Rigaku
_diffrn_measurement_method       \w
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         2
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  150
_diffrn_standards_decay_%        none
_diffrn_reflns_number            17519
_diffrn_reflns_av_R_equivalents  0.0354
_diffrn_reflns_av_sigmaI/netI    0.0175
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -36
_diffrn_reflns_limit_l_max       36
_diffrn_reflns_theta_min         2.67
_diffrn_reflns_theta_max         25.00
_reflns_number_total             1699
_reflns_number_gt                1674
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku/MSC Inc., 2006)'
_computing_cell_refinement       'CrystalClear (Rigaku/MSC Inc., 2006)'
_computing_data_reduction        'CrystalClear (Rigaku/MSC Inc., 2006)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXS-97 (Sheldrick, 2008)'
_computing_molecular_graphics    'SHELXS (Sheldrick, 2008)'
_computing_publication_material  'SHELXS (Sheldrick, 2008)'

_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^)+(0.0765P)^2^+3.0112P] 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_number_reflns         1699
_refine_ls_number_parameters     136
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0764
_refine_ls_R_factor_gt           0.0754
_refine_ls_wR_factor_ref         0.1813
_refine_ls_wR_factor_gt          0.1805
_refine_ls_goodness_of_fit_ref   1.008
_refine_ls_restrained_S_all      1.008
_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
N1 N 0.5100(4) 0.3341(2) 0.05294(8) 0.0441(6) Uani 1 1 d . . .
N2 N 0.4483(5) 0.2177(3) 0.03404(10) 0.0635(9) Uani 1 1 d . . .
N3 N 0.7437(6) 0.1846(4) 0.06414(13) 0.0850(11) Uani 1 1 d . . .
N4 N 0.2451(4) 0.5809(2) 0.11911(8) 0.0407(6) Uani 1 1 d . . .
N5 N 0.1676(4) 0.3599(2) 0.11509(8) 0.0433(6) Uani 1 1 d . . .
C1 C 0.5899(6) 0.1307(3) 0.04114(12) 0.0571(9) Uani 1 1 d . . .
H1A H 0.5861 0.0411 0.0315 0.069 Uiso 1 1 calc R . .
C2 C 0.6927(6) 0.3112(4) 0.07086(15) 0.0713(11) Uani 1 1 d . . .
H2A H 0.7720 0.3749 0.0858 0.086 Uiso 1 1 calc R . .
C3 C 0.3788(5) 0.4545(3) 0.05445(10) 0.0425(7) Uani 1 1 d . . .
H3A H 0.2811 0.4517 0.0303 0.051 Uiso 1 1 calc R . .
H3B H 0.4636 0.5351 0.0510 0.051 Uiso 1 1 calc R . .
C4 C 0.2639(4) 0.4624(2) 0.09666(9) 0.0367(6) Uani 1 1 d . . .
C5 C 0.1205(5) 0.5531(3) 0.15482(9) 0.0412(7) Uani 1 1 d . . .
C6 C 0.0424(5) 0.6351(3) 0.18815(11) 0.0556(9) Uani 1 1 d . . .
H6A H 0.0734 0.7273 0.1897 0.067 Uiso 1 1 calc R . .
C7 C -0.0823(6) 0.5737(4) 0.21861(12) 0.0637(10) Uani 1 1 d . . .
H7A H -0.1364 0.6256 0.2414 0.076 Uiso 1 1 calc R . .
C8 C -0.1300(6) 0.4361(4) 0.21644(12) 0.0663(10) Uani 1 1 d . . .
H8A H -0.2159 0.3984 0.2377 0.080 Uiso 1 1 calc R . .
C9 C -0.0534(5) 0.3539(3) 0.18360(12) 0.0587(9) Uani 1 1 d . . .
H9A H -0.0850 0.2618 0.1824 0.070 Uiso 1 1 calc R . .
C10 C 0.0739(4) 0.4151(3) 0.15220(10) 0.0420(7) 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
N1 0.0456(14) 0.0380(14) 0.0487(14) -0.0047(11) 0.0049(11) 0.0001(11)
N2 0.080(2) 0.0421(16) 0.0688(19) -0.0162(13) 0.0087(16) -0.0091(15)
N3 0.079(2) 0.066(2) 0.110(3) 0.014(2) 0.025(2) 0.0375(19)
N4 0.0471(13) 0.0291(12) 0.0459(13) -0.0031(10) -0.0003(11) 0.0010(11)
N5 0.0462(13) 0.0286(12) 0.0550(15) -0.0004(10) 0.0050(12) -0.0024(10)
C1 0.072(2) 0.0288(15) 0.070(2) -0.0061(14) 0.0272(19) 0.0123(17)
C2 0.048(2) 0.065(2) 0.101(3) -0.008(2) -0.009(2) 0.0120(18)
C3 0.0450(16) 0.0330(15) 0.0495(16) 0.0009(12) 0.0009(14) -0.0002(12)
C4 0.0364(14) 0.0258(13) 0.0478(15) -0.0020(11) -0.0053(13) 0.0014(11)
C5 0.0435(16) 0.0364(15) 0.0438(15) -0.0019(12) -0.0028(13) 0.0039(12)
C6 0.065(2) 0.0454(17) 0.0563(19) -0.0071(15) -0.0004(17) 0.0087(16)
C7 0.067(2) 0.069(2) 0.055(2) -0.0050(17) 0.0067(17) 0.0151(19)
C8 0.061(2) 0.079(3) 0.059(2) 0.0102(19) 0.0156(18) 0.005(2)
C9 0.060(2) 0.0474(18) 0.069(2) 0.0083(16) 0.0111(17) -0.0053(16)
C10 0.0415(15) 0.0360(15) 0.0485(16) 0.0026(12) -0.0008(13) 0.0029(13)

_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
N1 C2 1.321(4) . ?
N1 N2 1.343(4) . ?
N1 C3 1.458(4) . ?
N2 C1 1.271(4) . ?
N3 C2 1.305(5) . ?
N3 C1 1.328(5) . ?
N4 C4 1.358(3) . ?
N4 C5 1.382(4) . ?
N5 C4 1.312(3) . ?
N5 C10 1.394(4) . ?
C1 H1A 0.9300 . ?
C2 H2A 0.9300 . ?
C3 C4 1.489(4) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C5 C6 1.392(4) . ?
C5 C10 1.394(4) . ?
C6 C7 1.370(5) . ?
C6 H6A 0.9300 . ?
C7 C8 1.391(6) . ?
C7 H7A 0.9300 . ?
C8 C9 1.380(5) . ?
C8 H8A 0.9300 . ?
C9 C10 1.399(4) . ?
C9 H9A 0.9300 . ?

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
C2 N1 N2 107.3(3) . . ?
C2 N1 C3 130.3(3) . . ?
N2 N1 C3 122.3(3) . . ?
C1 N2 N1 106.7(3) . . ?
C2 N3 C1 105.9(3) . . ?
C4 N4 C5 106.3(2) . . ?
C4 N5 C10 104.7(2) . . ?
N2 C1 N3 111.1(3) . . ?
N2 C1 H1A 124.4 . . ?
N3 C1 H1A 124.4 . . ?
N3 C2 N1 108.9(4) . . ?
N3 C2 H2A 125.5 . . ?
N1 C2 H2A 125.5 . . ?
N1 C3 C4 111.1(2) . . ?
N1 C3 H3A 109.4 . . ?
C4 C3 H3A 109.4 . . ?
N1 C3 H3B 109.4 . . ?
C4 C3 H3B 109.4 . . ?
H3A C3 H3B 108.0 . . ?
N5 C4 N4 113.7(2) . . ?
N5 C4 C3 124.5(2) . . ?
N4 C4 C3 121.7(2) . . ?
N4 C5 C6 132.2(3) . . ?
N4 C5 C10 105.9(2) . . ?
C6 C5 C10 121.9(3) . . ?
C7 C6 C5 116.9(3) . . ?
C7 C6 H6A 121.5 . . ?
C5 C6 H6A 121.5 . . ?
C6 C7 C8 121.8(3) . . ?
C6 C7 H7A 119.1 . . ?
C8 C7 H7A 119.1 . . ?
C9 C8 C7 121.7(3) . . ?
C9 C8 H8A 119.1 . . ?
C7 C8 H8A 119.1 . . ?
C8 C9 C10 117.1(3) . . ?
C8 C9 H9A 121.4 . . ?
C10 C9 H9A 121.4 . . ?
C5 C10 N5 109.4(2) . . ?
C5 C10 C9 120.5(3) . . ?
N5 C10 C9 130.1(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
C2 N1 N2 C1 0.5(4) . . . . ?
C3 N1 N2 C1 -175.1(3) . . . . ?
N1 N2 C1 N3 0.1(4) . . . . ?
C2 N3 C1 N2 -0.6(5) . . . . ?
C1 N3 C2 N1 0.9(5) . . . . ?
N2 N1 C2 N3 -0.9(4) . . . . ?
C3 N1 C2 N3 174.3(3) . . . . ?
C2 N1 C3 C4 -79.0(4) . . . . ?
N2 N1 C3 C4 95.5(3) . . . . ?
C10 N5 C4 N4 1.3(3) . . . . ?
C10 N5 C4 C3 -176.9(3) . . . . ?
C5 N4 C4 N5 -1.7(3) . . . . ?
C5 N4 C4 C3 176.6(3) . . . . ?
N1 C3 C4 N5 -45.4(4) . . . . ?
N1 C3 C4 N4 136.6(3) . . . . ?
C4 N4 C5 C6 -177.4(3) . . . . ?
C4 N4 C5 C10 1.3(3) . . . . ?
N4 C5 C6 C7 178.8(3) . . . . ?
C10 C5 C6 C7 0.3(5) . . . . ?
C5 C6 C7 C8 -0.3(5) . . . . ?
C6 C7 C8 C9 0.4(6) . . . . ?
C7 C8 C9 C10 -0.4(6) . . . . ?
N4 C5 C10 N5 -0.5(3) . . . . ?
C6 C5 C10 N5 178.3(3) . . . . ?
N4 C5 C10 C9 -179.2(3) . . . . ?
C6 C5 C10 C9 -0.4(5) . . . . ?
C4 N5 C10 C5 -0.4(3) . . . . ?
C4 N5 C10 C9 178.1(3) . . . . ?
C8 C9 C10 C5 0.5(5) . . . . ?
C8 C9 C10 N5 -177.9(3) . . . . ?

_diffrn_measured_fraction_theta_max 0.999
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 0.999
_refine_diff_density_max         0.525
_refine_diff_density_min         -0.488
_refine_diff_density_rms         0.050