# Supplementary Material (ESI) for PCCP
# This journal is (c) the Owner Societies 2009

data_global
_journal_name_full               CrystEngComm

_journal_coden_Cambridge         1350

_publ_contact_author_name        'Qi-Yu Zheng'
_publ_contact_author_email       ZHENGQY@ICCAS.AC.CN

_publ_section_title              
;
Construction of 3-fold interpenetrated
pcu organic frameworks from methanetetrabenzoic acid with
zigzag bipyridines
;
loop_
_publ_author_name
'Qi-Yu Zheng'
'Zhi-Tang Huang'
'Yong-Biao Men'
'Junliang Sun'

# Attachment 'HMTB_bipy_ete.cif'

data_HMTB_bipy_ete
_database_code_depnum_ccdc_archive 'CCDC 735010'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C29 H20 O8 C12 H10 N2'
_chemical_formula_sum            'C41 H30 N2 O8'
_chemical_formula_weight         678.67

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   C2/c

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

_cell_length_a                   16.962(3)
_cell_length_b                   7.9204(16)
_cell_length_c                   25.187(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 105.45(3)
_cell_angle_gamma                90.00
_cell_volume                     3261.3(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    390
_cell_measurement_theta_min      2.17
_cell_measurement_theta_max      27.48

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.39
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.18
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.382
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1416
_exptl_absorpt_coefficient_mu    0.097
_exptl_absorpt_correction_type   Multi-scan
_exptl_absorpt_correction_T_min  0.9632
_exptl_absorpt_correction_T_max  0.9828
_exptl_absorpt_process_details   'CrystalClear (Rigaku Inc., 2008)'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Saturn724+ CCD'
_diffrn_measurement_method       'ω scans at fixed χ = 45°'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            11813
_diffrn_reflns_av_R_equivalents  0.0312
_diffrn_reflns_av_sigmaI/netI    0.0271
_diffrn_reflns_limit_h_min       -19
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_l_min       -32
_diffrn_reflns_limit_l_max       32
_diffrn_reflns_theta_min         2.49
_diffrn_reflns_theta_max         27.48
_reflns_number_total             3729
_reflns_number_gt                3400
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'CrystalClear (Rigaku Inc., 2008)'
_computing_cell_refinement       'CrystalClear (Rigaku Inc., 2008)'
_computing_data_reduction        'CrystalClear (Rigaku Inc., 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'XP in Siemens SHELXTL (Sheldrick, 1994)'
_computing_publication_material  'SHELX97 (Sheldrick, 1997)'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0581P)²+3.1056P] where P=(Fo²+2Fc²)/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         3729
_refine_ls_number_parameters     231
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0579
_refine_ls_R_factor_gt           0.0519
_refine_ls_wR_factor_ref         0.1315
_refine_ls_wR_factor_gt          0.1275
_refine_ls_goodness_of_fit_ref   1.096
_refine_ls_restrained_S_all      1.096
_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
O1 O 0.03721(7) 1.56546(16) 0.08721(5) 0.0381(3) Uani 1 1 d . . .
H1 H 0.0545 1.6495 0.0733 0.057 Uiso 1 1 d R . .
O2 O 0.16831(8) 1.54256(16) 0.13521(6) 0.0389(3) Uani 1 1 d . . .
O3 O 0.25797(8) 0.33682(16) 0.32604(5) 0.0359(3) Uani 1 1 d . . .
H3 H 0.2785 0.2494 0.3431 0.054 Uiso 1 1 d R . .
O4 O 0.20750(7) 0.35192(15) 0.39928(5) 0.0338(3) Uani 1 1 d . . .
N1 N 0.08535(9) 1.17531(19) 0.54244(6) 0.0347(3) Uani 1 1 d . . .
C1 C 0.0000 0.9541(3) 0.2500 0.0212(4) Uani 1 2 d S . .
C2 C 0.02875(9) 1.07683(18) 0.21128(6) 0.0219(3) Uani 1 1 d . . .
C3 C -0.03011(9) 1.16446(19) 0.17143(6) 0.0242(3) Uani 1 1 d . . .
H3A H -0.0861 1.1341 0.1648 0.029 Uiso 1 1 calc R . .
C4 C -0.00844(10) 1.29493(19) 0.14141(6) 0.0256(3) Uani 1 1 d . . .
H4A H -0.0493 1.3518 0.1141 0.031 Uiso 1 1 calc R . .
C5 C 0.07314(10) 1.34255(19) 0.15127(6) 0.0245(3) Uani 1 1 d . . .
C6 C 0.13252(10) 1.2544(2) 0.19003(7) 0.0261(3) Uani 1 1 d . . .
H6A H 0.1885 1.2843 0.1963 0.031 Uiso 1 1 calc R . .
C7 C 0.11049(9) 1.12274(19) 0.21970(6) 0.0245(3) Uani 1 1 d . . .
H7A H 0.1517 1.0633 0.2460 0.029 Uiso 1 1 calc R . .
C8 C 0.09742(10) 1.4929(2) 0.12322(7) 0.0274(3) Uani 1 1 d . . .
C9 C 0.06687(9) 0.83096(18) 0.28101(6) 0.0214(3) Uani 1 1 d . . .
C10 C 0.11237(9) 0.74119(19) 0.25158(6) 0.0242(3) Uani 1 1 d . . .
H10A H 0.1087 0.7718 0.2145 0.029 Uiso 1 1 calc R . .
C11 C 0.16263(9) 0.60849(19) 0.27535(6) 0.0247(3) Uani 1 1 d . . .
H11A H 0.1937 0.5500 0.2549 0.030 Uiso 1 1 calc R . .
C12 C 0.16757(9) 0.56091(19) 0.32950(6) 0.0237(3) Uani 1 1 d . . .
C13 C 0.12404(10) 0.6519(2) 0.35962(6) 0.0258(3) Uani 1 1 d . . .
H13A H 0.1284 0.6222 0.3968 0.031 Uiso 1 1 calc R . .
C14 C 0.07435(10) 0.7854(2) 0.33565(6) 0.0252(3) Uani 1 1 d . . .
H14A H 0.0450 0.8466 0.3567 0.030 Uiso 1 1 calc R . .
C15 C 0.21335(9) 0.4076(2) 0.35551(6) 0.0257(3) Uani 1 1 d . . .
C16 C 0.12011(12) 1.2106(2) 0.50190(7) 0.0380(4) Uani 1 1 d . . .
H16A H 0.1135 1.3209 0.4865 0.046 Uiso 1 1 calc R . .
C17 C 0.16495(12) 1.0951(2) 0.48138(7) 0.0349(4) Uani 1 1 d . . .
H17A H 0.1871 1.1247 0.4517 0.042 Uiso 1 1 calc R . .
C18 C 0.17759(10) 0.9347(2) 0.50438(7) 0.0300(4) Uani 1 1 d . . .
C19 C 0.13902(11) 0.8957(2) 0.54542(8) 0.0354(4) Uani 1 1 d . . .
H19A H 0.1438 0.7858 0.5611 0.043 Uiso 1 1 calc R . .
C20 C 0.09383(12) 1.0183(2) 0.56301(8) 0.0363(4) Uani 1 1 d . . .
H20A H 0.0677 0.9902 0.5908 0.044 Uiso 1 1 calc R . .
C21 C 0.23377(11) 0.8201(2) 0.48684(7) 0.0313(4) Uani 1 1 d . . .
H21A H 0.2483 0.8480 0.4540 0.038 Uiso 1 1 calc R . .


_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C8 1.305(2) . ?
O1 H1 0.8400 . ?
O2 C8 1.224(2) . ?
O3 C15 1.318(2) . ?
O3 H3 0.8400 . ?
O4 C15 1.216(2) . ?
N1 C16 1.338(2) . ?
N1 C20 1.340(2) . ?
C1 C9 1.542(2) 2 ?
C1 C9 1.542(2) . ?
C1 C2 1.5448(19) 2 ?
C1 C2 1.5448(19) . ?
C2 C7 1.394(2) . ?
C2 C3 1.397(2) . ?
C3 C4 1.387(2) . ?
C3 H3A 0.9500 . ?
C4 C5 1.391(2) . ?
C4 H4A 0.9500 . ?
C5 C6 1.389(2) . ?
C5 C8 1.497(2) . ?
C6 C7 1.391(2) . ?
C6 H6A 0.9500 . ?
C7 H7A 0.9500 . ?
C9 C14 1.395(2) . ?
C9 C10 1.398(2) . ?
C10 C11 1.385(2) . ?
C10 H10A 0.9500 . ?
C11 C12 1.396(2) . ?
C11 H11A 0.9500 . ?
C12 C13 1.392(2) . ?
C12 C15 1.495(2) . ?
C13 C14 1.386(2) . ?
C13 H13A 0.9500 . ?
C14 H14A 0.9500 . ?
C16 C17 1.376(3) . ?
C16 H16A 0.9500 . ?
C17 C18 1.389(2) . ?
C17 H17A 0.9500 . ?
C18 C19 1.397(2) . ?
C18 C21 1.467(2) . ?
C19 C20 1.381(2) . ?
C19 H19A 0.9500 . ?
C20 H20A 0.9500 . ?
C21 C21 1.334(3) 7_566 ?
C21 H21A 0.9500 . ?

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
C8 O1 H1 110.1 . . ?
C15 O3 H3 106.6 . . ?
C16 N1 C20 117.73(15) . . ?
C9 C1 C9 101.47(16) 2 . ?
C9 C1 C2 113.87(8) 2 2 ?
C9 C1 C2 113.06(8) . 2 ?
C9 C1 C2 113.06(8) 2 . ?
C9 C1 C2 113.87(8) . . ?
C2 C1 C2 102.04(16) 2 . ?
C7 C2 C3 118.11(14) . . ?
C7 C2 C1 122.45(12) . . ?
C3 C2 C1 118.73(12) . . ?
C4 C3 C2 121.30(14) . . ?
C4 C3 H3A 119.4 . . ?
C2 C3 H3A 119.4 . . ?
C3 C4 C5 120.01(14) . . ?
C3 C4 H4A 120.0 . . ?
C5 C4 H4A 120.0 . . ?
C6 C5 C4 119.31(14) . . ?
C6 C5 C8 119.48(14) . . ?
C4 C5 C8 121.12(14) . . ?
C5 C6 C7 120.40(14) . . ?
C5 C6 H6A 119.8 . . ?
C7 C6 H6A 119.8 . . ?
C6 C7 C2 120.83(14) . . ?
C6 C7 H7A 119.6 . . ?
C2 C7 H7A 119.6 . . ?
O2 C8 O1 124.45(15) . . ?
O2 C8 C5 120.97(15) . . ?
O1 C8 C5 114.56(14) . . ?
C14 C9 C10 118.25(14) . . ?
C14 C9 C1 121.65(12) . . ?
C10 C9 C1 119.25(12) . . ?
C11 C10 C9 121.32(14) . . ?
C11 C10 H10A 119.3 . . ?
C9 C10 H10A 119.3 . . ?
C10 C11 C12 119.81(14) . . ?
C10 C11 H11A 120.1 . . ?
C12 C11 H11A 120.1 . . ?
C13 C12 C11 119.36(14) . . ?
C13 C12 C15 118.06(14) . . ?
C11 C12 C15 122.44(14) . . ?
C14 C13 C12 120.44(14) . . ?
C14 C13 H13A 119.8 . . ?
C12 C13 H13A 119.8 . . ?
C13 C14 C9 120.78(14) . . ?
C13 C14 H14A 119.6 . . ?
C9 C14 H14A 119.6 . . ?
O4 C15 O3 123.65(15) . . ?
O4 C15 C12 122.26(15) . . ?
O3 C15 C12 114.06(14) . . ?
N1 C16 C17 123.23(17) . . ?
N1 C16 H16A 118.4 . . ?
C17 C16 H16A 118.4 . . ?
C16 C17 C18 119.42(16) . . ?
C16 C17 H17A 120.3 . . ?
C18 C17 H17A 120.3 . . ?
C17 C18 C19 117.37(16) . . ?
C17 C18 C21 118.75(15) . . ?
C19 C18 C21 123.78(16) . . ?
C20 C19 C18 119.42(17) . . ?
C20 C19 H19A 120.3 . . ?
C18 C19 H19A 120.3 . . ?
N1 C20 C19 122.69(17) . . ?
N1 C20 H20A 118.7 . . ?
C19 C20 H20A 118.7 . . ?
C21 C21 C18 125.5(2) 7_566 . ?
C21 C21 H21A 117.3 7_566 . ?
C18 C21 H21A 117.3 . . ?

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
C9 C1 C2 C7 -140.58(13) 2 . . . ?
C9 C1 C2 C7 -25.45(19) . . . . ?
C2 C1 C2 C7 96.71(14) 2 . . . ?
C9 C1 C2 C3 49.29(18) 2 . . . ?
C9 C1 C2 C3 164.41(13) . . . . ?
C2 C1 C2 C3 -73.43(12) 2 . . . ?
C7 C2 C3 C4 -0.8(2) . . . . ?
C1 C2 C3 C4 169.78(14) . . . . ?
C2 C3 C4 C5 -1.0(2) . . . . ?
C3 C4 C5 C6 2.2(2) . . . . ?
C3 C4 C5 C8 -174.34(14) . . . . ?
C4 C5 C6 C7 -1.6(2) . . . . ?
C8 C5 C6 C7 174.92(14) . . . . ?
C5 C6 C7 C2 -0.1(2) . . . . ?
C3 C2 C7 C6 1.3(2) . . . . ?
C1 C2 C7 C6 -168.88(14) . . . . ?
C6 C5 C8 O2 -2.4(2) . . . . ?
C4 C5 C8 O2 174.10(15) . . . . ?
C6 C5 C8 O1 179.35(14) . . . . ?
C4 C5 C8 O1 -4.1(2) . . . . ?
C9 C1 C9 C14 -96.39(14) 2 . . . ?
C2 C1 C9 C14 25.95(19) 2 . . . ?
C2 C1 C9 C14 141.82(14) . . . . ?
C9 C1 C9 C10 72.85(12) 2 . . . ?
C2 C1 C9 C10 -164.80(13) 2 . . . ?
C2 C1 C9 C10 -48.93(18) . . . . ?
C14 C9 C10 C11 1.1(2) . . . . ?
C1 C9 C10 C11 -168.52(14) . . . . ?
C9 C10 C11 C12 0.9(2) . . . . ?
C10 C11 C12 C13 -2.3(2) . . . . ?
C10 C11 C12 C15 173.19(14) . . . . ?
C11 C12 C13 C14 1.9(2) . . . . ?
C15 C12 C13 C14 -173.87(14) . . . . ?
C12 C13 C14 C9 0.1(2) . . . . ?
C10 C9 C14 C13 -1.6(2) . . . . ?
C1 C9 C14 C13 167.77(14) . . . . ?
C13 C12 C15 O4 7.0(2) . . . . ?
C11 C12 C15 O4 -168.57(15) . . . . ?
C13 C12 C15 O3 -174.94(14) . . . . ?
C11 C12 C15 O3 9.5(2) . . . . ?
C20 N1 C16 C17 -1.3(3) . . . . ?
N1 C16 C17 C18 -2.0(3) . . . . ?
C16 C17 C18 C19 4.0(3) . . . . ?
C16 C17 C18 C21 -172.49(17) . . . . ?
C17 C18 C19 C20 -3.0(3) . . . . ?
C21 C18 C19 C20 173.36(17) . . . . ?
C16 N1 C20 C19 2.4(3) . . . . ?
C18 C19 C20 N1 -0.3(3) . . . . ?
C17 C18 C21 C21 164.0(2) . . . 7_566 ?
C19 C18 C21 C21 -12.3(3) . . . 7_566 ?

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 H1 N1 0.84 1.74 2.5777(19) 177.2 6_585
O3 H3 O2 0.84 1.88 2.7014(18) 165.7 4_535

_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_theta_full        27.48
_diffrn_measured_fraction_theta_full 0.998
_refine_diff_density_max         0.263
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.049


# Attachment 'HMTB_azpy.cif'

data_HMTB_azpy
_database_code_depnum_ccdc_archive 'CCDC 735011'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C39 H28 N4 O8'
_chemical_formula_sum            'C39 H28 N4 O8'
_chemical_formula_weight         680.65

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'

_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   C2/c

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

_cell_length_a                   17.020(3)
_cell_length_b                   7.9746(16)
_cell_length_c                   24.621(5)
_cell_angle_alpha                90.00
_cell_angle_beta                 104.15(3)
_cell_angle_gamma                90.00
_cell_volume                     3240.3(11)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    765
_cell_measurement_theta_min      2.17
_cell_measurement_theta_max      27.48

_exptl_crystal_description       plate
_exptl_crystal_colour            red
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.24
_exptl_crystal_size_min          0.12
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.395
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1416
_exptl_absorpt_coefficient_mu    0.099
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9520
_exptl_absorpt_correction_T_max  0.9882
_exptl_absorpt_process_details   'ABSCOR by T.Higashi 8 March, 1995'

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      173(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Rigaku raxis Rapid IP Area Detector'
_diffrn_measurement_method       'ω scans at fixed χ = 45°'
_diffrn_detector_area_resol_mean ?
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            6567
_diffrn_reflns_av_R_equivalents  0.0304
_diffrn_reflns_av_sigmaI/netI    0.0530
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_h_max       22
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_limit_l_max       31
_diffrn_reflns_theta_min         2.47
_diffrn_reflns_theta_max         27.40
_reflns_number_total             3663
_reflns_number_gt                2956
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Rapid Auto(Rigaku 2001)'
_computing_cell_refinement       'Rapid Auto(Rigaku 2001)'
_computing_data_reduction        'Rapid Auto(Rigaku 2001)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    'XP in Siemens SHELXTL (Sheldrick, 1994)'
_computing_publication_material  'SHELX97 (Sheldrick, 1997)'

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

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'calc w=1/[σ²(Fo²)+(0.0543P)²+3.4004P] where P=(Fo²+2Fc²)/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         3663
_refine_ls_number_parameters     231
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0998
_refine_ls_R_factor_gt           0.0714
_refine_ls_wR_factor_ref         0.1464
_refine_ls_wR_factor_gt          0.1356
_refine_ls_goodness_of_fit_ref   1.175
_refine_ls_restrained_S_all      1.175
_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
O1 O 0.20062(10) 0.6297(2) 0.40116(7) 0.0275(4) Uani 1 1 d . . .
O2 O 0.25494(10) 0.6370(2) 0.32745(7) 0.0291(4) Uani 1 1 d . . .
H2A H 0.2745 0.7278 0.3420 0.044 Uiso 1 1 calc R . .
O3 O 0.17100(10) -0.5683(2) 0.13882(8) 0.0305(4) Uani 1 1 d . . .
O4 O 0.04491(11) -0.5735(2) 0.08420(8) 0.0343(5) Uani 1 1 d . . .
H4B H 0.0624 -0.6575 0.0703 0.051 Uiso 1 1 calc R . .
N1 N 0.40729(13) 0.6609(3) 0.46121(9) 0.0293(5) Uani 1 1 d . . .
N2 N 0.26041(15) 0.3092(3) 0.51559(9) 0.0377(6) Uani 1 1 d . . .
C1 C 0.0000 0.0276(4) 0.2500 0.0129(6) Uani 1 2 d S . .
C2 C 0.06531(12) 0.1508(3) 0.28184(9) 0.0141(4) Uani 1 1 d . . .
C3 C 0.06880(13) 0.1986(3) 0.33679(9) 0.0179(5) Uani 1 1 d . . .
H3A H 0.0376 0.1397 0.3577 0.021 Uiso 1 1 calc R . .
C4 C 0.11714(13) 0.3308(3) 0.36121(9) 0.0192(5) Uani 1 1 d . . .
H4A H 0.1189 0.3620 0.3987 0.023 Uiso 1 1 calc R . .
C5 C 0.16324(12) 0.4184(3) 0.33126(9) 0.0178(5) Uani 1 1 d . . .
C6 C 0.16202(12) 0.3684(3) 0.27706(9) 0.0177(5) Uani 1 1 d . . .
H6A H 0.1946 0.4251 0.2566 0.021 Uiso 1 1 calc R . .
C7 C 0.11344(12) 0.2361(3) 0.25275(9) 0.0170(4) Uani 1 1 d . . .
H7A H 0.1129 0.2030 0.2156 0.020 Uiso 1 1 calc R . .
C8 C 0.20852(13) 0.5712(3) 0.35750(9) 0.0188(5) Uani 1 1 d . . .
C9 C 0.03042(12) -0.0949(3) 0.21105(9) 0.0156(4) Uani 1 1 d . . .
C10 C 0.11137(13) -0.1433(3) 0.22148(9) 0.0189(5) Uani 1 1 d . . .
H10A H 0.1510 -0.0858 0.2491 0.023 Uiso 1 1 calc R . .
C11 C 0.13469(13) -0.2744(3) 0.19203(10) 0.0199(5) Uani 1 1 d . . .
H11A H 0.1901 -0.3059 0.1996 0.024 Uiso 1 1 calc R . .
C12 C 0.07788(13) -0.3598(3) 0.15168(9) 0.0189(5) Uani 1 1 d . . .
C13 C -0.00276(13) -0.3088(3) 0.13978(9) 0.0191(5) Uani 1 1 d . . .
H13A H -0.0420 -0.3636 0.1112 0.023 Uiso 1 1 calc R . .
C14 C -0.02581(13) -0.1790(3) 0.16939(9) 0.0182(5) Uani 1 1 d . . .
H14A H -0.0811 -0.1462 0.1612 0.022 Uiso 1 1 calc R . .
C15 C 0.10304(13) -0.5102(3) 0.12395(10) 0.0200(5) Uani 1 1 d . . .
C16 C 0.31589(15) 0.4192(3) 0.49684(10) 0.0284(6) Uani 1 1 d . . .
C17 C 0.32392(16) 0.5747(3) 0.52100(11) 0.0315(6) Uani 1 1 d . . .
H17A H 0.2991 0.6005 0.5506 0.038 Uiso 1 1 calc R . .
C18 C 0.36897(16) 0.6927(3) 0.50119(11) 0.0315(6) Uani 1 1 d . . .
H18A H 0.3729 0.8022 0.5168 0.038 Uiso 1 1 calc R . .
C19 C 0.40221(17) 0.5057(3) 0.44012(12) 0.0355(7) Uani 1 1 d . . .
H19A H 0.4312 0.4804 0.4127 0.043 Uiso 1 1 calc R . .
C20 C 0.35680(17) 0.3809(3) 0.45634(12) 0.0351(6) Uani 1 1 d . . .
H20A H 0.3537 0.2721 0.4402 0.042 Uiso 1 1 calc R . .


_geom_special_details            
;
All esds (except the esd in the dihedral angle between two l.s. planes)
are estimated using the full covariance matrix. The cell esds are taken
into account individually in the estimation of esds in distances, angles
and torsion angles; correlations between esds in cell parameters are only
used when they are defined by crystal symmetry. An approximate (isotropic)
treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C8 1.209(3) . ?
O2 C8 1.316(3) . ?
O2 H2A 0.8400 . ?
O3 C15 1.216(3) . ?
O4 C15 1.311(3) . ?
O4 H4B 0.8400 . ?
N1 C18 1.331(3) . ?
N1 C19 1.336(3) . ?
N2 N2 1.214(4) 7_556 ?
N2 C16 1.445(3) . ?
C1 C9 1.544(3) . ?
C1 C9 1.544(3) 2 ?
C1 C2 1.545(3) 2 ?
C1 C2 1.545(3) . ?
C2 C7 1.391(3) . ?
C2 C3 1.393(3) . ?
C3 C4 1.381(3) . ?
C3 H3A 0.9500 . ?
C4 C5 1.389(3) . ?
C4 H4A 0.9500 . ?
C5 C6 1.388(3) . ?
C5 C8 1.500(3) . ?
C6 C7 1.383(3) . ?
C6 H6A 0.9500 . ?
C7 H7A 0.9500 . ?
C9 C14 1.392(3) . ?
C9 C10 1.393(3) . ?
C10 C11 1.384(3) . ?
C10 H10A 0.9500 . ?
C11 C12 1.384(3) . ?
C11 H11A 0.9500 . ?
C12 C13 1.392(3) . ?
C12 C15 1.494(3) . ?
C13 C14 1.377(3) . ?
C13 H13A 0.9500 . ?
C14 H14A 0.9500 . ?
C16 C17 1.367(4) . ?
C16 C20 1.383(4) . ?
C17 C18 1.376(4) . ?
C17 H17A 0.9500 . ?
C18 H18A 0.9500 . ?
C19 C20 1.378(4) . ?
C19 H19A 0.9500 . ?
C20 H20A 0.9500 . ?

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
C8 O2 H2A 109.5 . . ?
C15 O4 H4B 109.5 . . ?
C18 N1 C19 117.8(2) . . ?
N2 N2 C16 112.5(3) 7_556 . ?
C9 C1 C9 101.5(2) . 2 ?
C9 C1 C2 113.31(11) . 2 ?
C9 C1 C2 114.09(11) 2 2 ?
C9 C1 C2 114.09(11) . . ?
C9 C1 C2 113.31(11) 2 . ?
C2 C1 C2 101.1(2) 2 . ?
C7 C2 C3 118.4(2) . . ?
C7 C2 C1 119.40(17) . . ?
C3 C2 C1 121.43(17) . . ?
C4 C3 C2 120.8(2) . . ?
C4 C3 H3A 119.6 . . ?
C2 C3 H3A 119.6 . . ?
C3 C4 C5 120.4(2) . . ?
C3 C4 H4A 119.8 . . ?
C5 C4 H4A 119.8 . . ?
C6 C5 C4 119.2(2) . . ?
C6 C5 C8 122.2(2) . . ?
C4 C5 C8 118.5(2) . . ?
C7 C6 C5 120.1(2) . . ?
C7 C6 H6A 119.9 . . ?
C5 C6 H6A 119.9 . . ?
C6 C7 C2 121.0(2) . . ?
C6 C7 H7A 119.5 . . ?
C2 C7 H7A 119.5 . . ?
O1 C8 O2 123.9(2) . . ?
O1 C8 C5 122.6(2) . . ?
O2 C8 C5 113.43(19) . . ?
C14 C9 C10 118.2(2) . . ?
C14 C9 C1 119.20(16) . . ?
C10 C9 C1 121.85(18) . . ?
C11 C10 C9 120.7(2) . . ?
C11 C10 H10A 119.7 . . ?
C9 C10 H10A 119.7 . . ?
C12 C11 C10 120.5(2) . . ?
C12 C11 H11A 119.7 . . ?
C10 C11 H11A 119.7 . . ?
C11 C12 C13 119.1(2) . . ?
C11 C12 C15 119.69(19) . . ?
C13 C12 C15 121.1(2) . . ?
C14 C13 C12 120.1(2) . . ?
C14 C13 H13A 119.9 . . ?
C12 C13 H13A 119.9 . . ?
C13 C14 C9 121.24(19) . . ?
C13 C14 H14A 119.4 . . ?
C9 C14 H14A 119.4 . . ?
O3 C15 O4 124.6(2) . . ?
O3 C15 C12 121.7(2) . . ?
O4 C15 C12 113.70(19) . . ?
C17 C16 C20 120.0(2) . . ?
C17 C16 N2 114.5(2) . . ?
C20 C16 N2 125.5(2) . . ?
C16 C17 C18 118.1(2) . . ?
C16 C17 H17A 121.0 . . ?
C18 C17 H17A 121.0 . . ?
N1 C18 C17 123.2(3) . . ?
N1 C18 H18A 118.4 . . ?
C17 C18 H18A 118.4 . . ?
N1 C19 C20 122.9(2) . . ?
N1 C19 H19A 118.5 . . ?
C20 C19 H19A 118.5 . . ?
C19 C20 C16 117.8(3) . . ?
C19 C20 H20A 121.1 . . ?
C16 C20 H20A 121.1 . . ?

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
C9 C1 C2 C7 47.3(3) . . . . ?
C9 C1 C2 C7 162.79(18) 2 . . . ?
C2 C1 C2 C7 -74.71(17) 2 . . . ?
C9 C1 C2 C3 -143.04(19) . . . . ?
C9 C1 C2 C3 -27.5(3) 2 . . . ?
C2 C1 C2 C3 95.0(2) 2 . . . ?
C7 C2 C3 C4 1.8(3) . . . . ?
C1 C2 C3 C4 -168.0(2) . . . . ?
C2 C3 C4 C5 0.0(3) . . . . ?
C3 C4 C5 C6 -1.9(3) . . . . ?
C3 C4 C5 C8 174.2(2) . . . . ?
C4 C5 C6 C7 2.0(3) . . . . ?
C8 C5 C6 C7 -174.0(2) . . . . ?
C5 C6 C7 C2 -0.2(3) . . . . ?
C3 C2 C7 C6 -1.8(3) . . . . ?
C1 C2 C7 C6 168.26(19) . . . . ?
C6 C5 C8 O1 169.0(2) . . . . ?
C4 C5 C8 O1 -7.0(3) . . . . ?
C6 C5 C8 O2 -8.9(3) . . . . ?
C4 C5 C8 O2 175.14(19) . . . . ?
C9 C1 C9 C14 75.15(18) 2 . . . ?
C2 C1 C9 C14 -47.6(3) 2 . . . ?
C2 C1 C9 C14 -162.60(18) . . . . ?
C9 C1 C9 C10 -94.9(2) 2 . . . ?
C2 C1 C9 C10 142.30(19) 2 . . . ?
C2 C1 C9 C10 27.3(3) . . . . ?
C14 C9 C10 C11 -1.5(3) . . . . ?
C1 C9 C10 C11 168.6(2) . . . . ?
C9 C10 C11 C12 -0.1(3) . . . . ?
C10 C11 C12 C13 2.1(3) . . . . ?
C10 C11 C12 C15 -174.6(2) . . . . ?
C11 C12 C13 C14 -2.4(3) . . . . ?
C15 C12 C13 C14 174.2(2) . . . . ?
C12 C13 C14 C9 0.8(3) . . . . ?
C10 C9 C14 C13 1.2(3) . . . . ?
C1 C9 C14 C13 -169.3(2) . . . . ?
C11 C12 C15 O3 5.8(3) . . . . ?
C13 C12 C15 O3 -170.8(2) . . . . ?
C11 C12 C15 O4 -176.0(2) . . . . ?
C13 C12 C15 O4 7.4(3) . . . . ?
N2 N2 C16 C17 163.1(3) 7_556 . . . ?
N2 N2 C16 C20 -14.3(5) 7_556 . . . ?
C20 C16 C17 C18 4.2(4) . . . . ?
N2 C16 C17 C18 -173.3(2) . . . . ?
C19 N1 C18 C17 -0.9(4) . . . . ?
C16 C17 C18 N1 -2.5(4) . . . . ?
C18 N1 C19 C20 2.6(4) . . . . ?
N1 C19 C20 C16 -0.9(4) . . . . ?
C17 C16 C20 C19 -2.6(4) . . . . ?
N2 C16 C20 C19 174.6(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2A O3 0.84 1.87 2.700(2) 167.3 4_565
O4 H4B N1 0.84 1.78 2.616(3) 176.2 4_535

_diffrn_measured_fraction_theta_max 0.994
_diffrn_reflns_theta_full        27.40
_diffrn_measured_fraction_theta_full 0.994
_refine_diff_density_max         0.681
_refine_diff_density_min         -0.278
_refine_diff_density_rms         0.055

