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

data_global
_journal_name_full               CrystEngComm

_journal_coden_Cambridge         1350

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

_publ_section_title              
;
Organic hydrogen-bonded interpenetrating diamondoid
frameworks from modular self-assembly of methanetetrabenzoic acid with
linkers
;
loop_
_publ_author_name
'Qi-Yu Zheng'
'Zhi-Tang Huang'
'Yong-Biao Men'
'Junliang Sun'

# Attachment 'HMTBphen_708658_-revised.cif'

data_myb1
_database_code_depnum_ccdc_archive 'CCDC 708658'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C29 H20 O8, C12 H8 N2'
_chemical_formula_sum            'C41 H28 N2 O8'
_chemical_formula_weight         676.65

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                   25.574(5)
_cell_length_b                   8.6352(17)
_cell_length_c                   17.905(4)
_cell_angle_alpha                90.00
_cell_angle_beta                 122.61(3)
_cell_angle_gamma                90.00
_cell_volume                     3330.5(16)
_cell_formula_units_Z            4
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    786
_cell_measurement_theta_min      2.17
_cell_measurement_theta_max      27.48

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.27
_exptl_crystal_size_min          0.25
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.349
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             1408
_exptl_absorpt_coefficient_mu    0.095
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9604
_exptl_absorpt_correction_T_max  0.9767
_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            5209
_diffrn_reflns_av_R_equivalents  0.0277
_diffrn_reflns_av_sigmaI/netI    0.0480
_diffrn_reflns_limit_h_min       -29
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_theta_min         2.32
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2931
_reflns_number_gt                2373
_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)+(0.0560P)²+0.7938P] 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         2931
_refine_ls_number_parameters     231
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0844
_refine_ls_R_factor_gt           0.0575
_refine_ls_wR_factor_ref         0.1256
_refine_ls_wR_factor_gt          0.1162
_refine_ls_goodness_of_fit_ref   1.189
_refine_ls_restrained_S_all      1.189
_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 -0.04655(8) 1.84400(19) -0.02322(11) 0.0377(5) Uani 1 1 d . . .
O2 O 0.05527(8) 1.8688(2) 0.07501(12) 0.0396(5) Uani 1 1 d . . .
H2A H 0.0483 1.9596 0.0550 0.059 Uiso 1 1 calc R . .
O3 O 0.20169(8) 0.74433(19) 0.33975(11) 0.0335(4) Uani 1 1 d . . .
O4 O 0.17781(7) 0.69688(19) 0.44047(10) 0.0300(4) Uani 1 1 d . . .
H4 H 0.2005 0.6191 0.4509 0.045 Uiso 1 1 calc R . .
N1 N 0.23202(8) 0.4063(2) 0.47749(12) 0.0232(4) Uani 1 1 d . . .
C1 C 0.0000 1.2886(3) 0.2500 0.0170(6) Uani 1 2 d S . .
C2 C 0.00251(9) 1.4020(2) 0.18538(14) 0.0191(5) Uani 1 1 d . . .
C3 C -0.04958(10) 1.4411(3) 0.10396(15) 0.0238(5) Uani 1 1 d . . .
H3A H -0.0865 1.3821 0.0809 0.029 Uiso 1 1 calc R . .
C4 C -0.04848(10) 1.5654(3) 0.05578(15) 0.0255(5) Uani 1 1 d . . .
H4A H -0.0847 1.5913 0.0004 0.031 Uiso 1 1 calc R . .
C5 C 0.00499(10) 1.6519(2) 0.08779(15) 0.0220(5) Uani 1 1 d . . .
C6 C 0.05852(10) 1.6096(3) 0.16775(15) 0.0244(5) Uani 1 1 d . . .
H6A H 0.0960 1.6657 0.1892 0.029 Uiso 1 1 calc R . .
C7 C 0.05715(10) 1.4866(2) 0.21559(15) 0.0221(5) Uani 1 1 d . . .
H7A H 0.0939 1.4586 0.2700 0.027 Uiso 1 1 calc R . .
C9 C 0.00401(10) 1.7961(3) 0.04233(15) 0.0242(5) Uani 1 1 d . . .
C10 C 0.05512(10) 1.1747(2) 0.29415(14) 0.0189(5) Uani 1 1 d . . .
C11 C 0.08625(10) 1.1351(2) 0.25254(15) 0.0220(5) Uani 1 1 d . . .
H11A H 0.0799 1.1946 0.2037 0.026 Uiso 1 1 calc R . .
C12 C 0.12628(10) 1.0099(3) 0.28197(15) 0.0233(5) Uani 1 1 d . . .
H12A H 0.1470 0.9836 0.2528 0.028 Uiso 1 1 calc R . .
C13 C 0.13656(10) 0.9223(2) 0.35348(14) 0.0202(5) Uani 1 1 d . . .
C14 C 0.10750(10) 0.9640(3) 0.39757(14) 0.0219(5) Uani 1 1 d . . .
H14A H 0.1152 0.9068 0.4478 0.026 Uiso 1 1 calc R . .
C15 C 0.06747(10) 1.0890(2) 0.36793(15) 0.0229(5) Uani 1 1 d . . .
H15A H 0.0479 1.1171 0.3985 0.027 Uiso 1 1 calc R . .
C16 C 0.17575(10) 0.7806(3) 0.37727(14) 0.0217(5) Uani 1 1 d . . .
C17 C 0.27427(12) 0.3060(3) 0.32001(18) 0.0370(6) Uani 1 1 d . . .
H17A H 0.2759 0.3527 0.2733 0.044 Uiso 1 1 calc R . .
C18 C 0.25507(12) 0.3906(3) 0.36468(17) 0.0346(6) Uani 1 1 d . . .
H18A H 0.2437 0.4960 0.3495 0.041 Uiso 1 1 calc R . .
C19 C 0.25190(10) 0.3219(3) 0.43413(15) 0.0225(5) Uani 1 1 d . . .
C20 C 0.23021(9) 0.3365(3) 0.54333(14) 0.0199(5) Uani 1 1 d . . .
C21 C 0.21065(10) 0.4210(3) 0.59210(15) 0.0246(5) Uani 1 1 d . . .
H21A H 0.1993 0.5268 0.5786 0.030 Uiso 1 1 calc R . .
C22 C 0.20809(11) 0.3511(3) 0.65788(16) 0.0288(6) Uani 1 1 d . . .
H22A H 0.1943 0.4081 0.6895 0.035 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 C9 1.259(3) . ?
O2 C9 1.276(3) . ?
O2 H2A 0.8400 . ?
O3 C16 1.212(3) . ?
O4 C16 1.319(3) . ?
O4 H4 0.8400 . ?
N1 C20 1.347(3) . ?
N1 C19 1.348(3) . ?
C1 C10 1.542(3) 2 ?
C1 C10 1.542(3) . ?
C1 C2 1.543(3) 2 ?
C1 C2 1.543(3) . ?
C2 C3 1.386(3) . ?
C2 C7 1.402(3) . ?
C3 C4 1.386(3) . ?
C3 H3A 0.9500 . ?
C4 C5 1.382(3) . ?
C4 H4A 0.9500 . ?
C5 C6 1.394(3) . ?
C5 C9 1.481(3) . ?
C6 C7 1.377(3) . ?
C6 H6A 0.9500 . ?
C7 H7A 0.9500 . ?
C10 C15 1.394(3) . ?
C10 C11 1.395(3) . ?
C11 C12 1.383(3) . ?
C11 H11A 0.9500 . ?
C12 C13 1.385(3) . ?
C12 H12A 0.9500 . ?
C13 C14 1.392(3) . ?
C13 C16 1.491(3) . ?
C14 C15 1.381(3) . ?
C14 H14A 0.9500 . ?
C15 H15A 0.9500 . ?
C17 C18 1.355(3) . ?
C17 C22 1.417(3) 7_556 ?
C17 H17A 0.9500 . ?
C18 C19 1.419(3) . ?
C18 H18A 0.9500 . ?
C19 C20 1.429(3) 7_556 ?
C20 C21 1.420(3) . ?
C20 C19 1.429(3) 7_556 ?
C21 C22 1.356(3) . ?
C21 H21A 0.9500 . ?
C22 C17 1.417(3) 7_556 ?
C22 H22A 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
C9 O2 H2A 109.5 . . ?
C16 O4 H4 109.5 . . ?
C20 N1 C19 117.59(19) . . ?
C10 C1 C10 100.7(2) 2 . ?
C10 C1 C2 113.16(11) 2 2 ?
C10 C1 C2 114.60(11) . 2 ?
C10 C1 C2 114.60(11) 2 . ?
C10 C1 C2 113.16(11) . . ?
C2 C1 C2 101.2(2) 2 . ?
C3 C2 C7 118.2(2) . . ?
C3 C2 C1 122.60(17) . . ?
C7 C2 C1 118.49(17) . . ?
C2 C3 C4 120.9(2) . . ?
C2 C3 H3A 119.6 . . ?
C4 C3 H3A 119.6 . . ?
C5 C4 C3 120.5(2) . . ?
C5 C4 H4A 119.8 . . ?
C3 C4 H4A 119.8 . . ?
C4 C5 C6 119.3(2) . . ?
C4 C5 C9 120.4(2) . . ?
C6 C5 C9 120.0(2) . . ?
C7 C6 C5 120.0(2) . . ?
C7 C6 H6A 120.0 . . ?
C5 C6 H6A 120.0 . . ?
C6 C7 C2 121.1(2) . . ?
C6 C7 H7A 119.5 . . ?
C2 C7 H7A 119.5 . . ?
O1 C9 O2 123.4(2) . . ?
O1 C9 C5 119.6(2) . . ?
O2 C9 C5 116.9(2) . . ?
C15 C10 C11 118.2(2) . . ?
C15 C10 C1 120.15(17) . . ?
C11 C10 C1 120.64(17) . . ?
C12 C11 C10 120.4(2) . . ?
C12 C11 H11A 119.8 . . ?
C10 C11 H11A 119.8 . . ?
C11 C12 C13 120.8(2) . . ?
C11 C12 H12A 119.6 . . ?
C13 C12 H12A 119.6 . . ?
C12 C13 C14 119.3(2) . . ?
C12 C13 C16 118.41(19) . . ?
C14 C13 C16 122.2(2) . . ?
C15 C14 C13 119.7(2) . . ?
C15 C14 H14A 120.1 . . ?
C13 C14 H14A 120.1 . . ?
C14 C15 C10 121.4(2) . . ?
C14 C15 H15A 119.3 . . ?
C10 C15 H15A 119.3 . . ?
O3 C16 O4 123.6(2) . . ?
O3 C16 C13 122.5(2) . . ?
O4 C16 C13 113.85(19) . . ?
C18 C17 C22 120.9(2) . 7_556 ?
C18 C17 H17A 119.6 . . ?
C22 C17 H17A 119.6 7_556 . ?
C17 C18 C19 120.1(2) . . ?
C17 C18 H18A 119.9 . . ?
C19 C18 H18A 119.9 . . ?
N1 C19 C18 119.7(2) . . ?
N1 C19 C20 121.2(2) . 7_556 ?
C18 C19 C20 119.1(2) . 7_556 ?
N1 C20 C21 119.8(2) . . ?
N1 C20 C19 121.25(19) . 7_556 ?
C21 C20 C19 118.9(2) . 7_556 ?
C22 C21 C20 120.2(2) . . ?
C22 C21 H21A 119.9 . . ?
C20 C21 H21A 119.9 . . ?
C21 C22 C17 120.8(2) . 7_556 ?
C21 C22 H22A 119.6 . . ?
C17 C22 H22A 119.6 7_556 . ?

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
C10 C1 C2 C3 23.5(3) 2 . . . ?
C10 C1 C2 C3 138.2(2) . . . . ?
C2 C1 C2 C3 -98.6(2) 2 . . . ?
C10 C1 C2 C7 -166.63(18) 2 . . . ?
C10 C1 C2 C7 -51.9(3) . . . . ?
C2 C1 C2 C7 71.23(17) 2 . . . ?
C7 C2 C3 C4 -3.1(3) . . . . ?
C1 C2 C3 C4 166.8(2) . . . . ?
C2 C3 C4 C5 0.7(3) . . . . ?
C3 C4 C5 C6 2.2(3) . . . . ?
C3 C4 C5 C9 -172.1(2) . . . . ?
C4 C5 C6 C7 -2.5(3) . . . . ?
C9 C5 C6 C7 171.8(2) . . . . ?
C5 C6 C7 C2 0.0(3) . . . . ?
C3 C2 C7 C6 2.8(3) . . . . ?
C1 C2 C7 C6 -167.5(2) . . . . ?
C4 C5 C9 O1 3.6(3) . . . . ?
C6 C5 C9 O1 -170.7(2) . . . . ?
C4 C5 C9 O2 -179.2(2) . . . . ?
C6 C5 C9 O2 6.6(3) . . . . ?
C10 C1 C10 C15 -71.57(18) 2 . . . ?
C2 C1 C10 C15 50.2(3) 2 . . . ?
C2 C1 C10 C15 165.63(18) . . . . ?
C10 C1 C10 C11 97.0(2) 2 . . . ?
C2 C1 C10 C11 -141.24(19) 2 . . . ?
C2 C1 C10 C11 -25.8(3) . . . . ?
C15 C10 C11 C12 2.7(3) . . . . ?
C1 C10 C11 C12 -166.1(2) . . . . ?
C10 C11 C12 C13 -0.5(3) . . . . ?
C11 C12 C13 C14 -1.8(3) . . . . ?
C11 C12 C13 C16 174.7(2) . . . . ?
C12 C13 C14 C15 1.9(3) . . . . ?
C16 C13 C14 C15 -174.4(2) . . . . ?
C13 C14 C15 C10 0.3(3) . . . . ?
C11 C10 C15 C14 -2.6(3) . . . . ?
C1 C10 C15 C14 166.2(2) . . . . ?
C12 C13 C16 O3 4.3(3) . . . . ?
C14 C13 C16 O3 -179.2(2) . . . . ?
C12 C13 C16 O4 -173.66(19) . . . . ?
C14 C13 C16 O4 2.8(3) . . . . ?
C22 C17 C18 C19 -0.5(4) 7_556 . . . ?
C20 N1 C19 C18 -179.6(2) . . . . ?
C20 N1 C19 C20 0.6(3) . . . 7_556 ?
C17 C18 C19 N1 -179.2(2) . . . . ?
C17 C18 C19 C20 0.6(4) . . . 7_556 ?
C19 N1 C20 C21 178.9(2) . . . . ?
C19 N1 C20 C19 -0.6(3) . . . 7_556 ?
N1 C20 C21 C22 179.3(2) . . . . ?
C19 C20 C21 C22 -1.1(3) 7_556 . . . ?
C20 C21 C22 C17 1.0(3) . . . 7_556 ?

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 O1 0.84 1.78 2.614(2) 170.8 5_595
O4 H4 N1 0.84 1.96 2.769(2) 161.6 .

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.221
_refine_diff_density_min         -0.272
_refine_diff_density_rms         0.051


# Attachment 'HMTBbipy_708659_-revised.cif'

data_myb2
_database_code_depnum_ccdc_archive 'CCDC 708659'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;
?
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C29 H20 O8, 2 C10 H8 N2'
_chemical_formula_sum            'C49 H36 N4 O8'
_chemical_formula_weight         808.82

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           Tetragonal
_symmetry_space_group_name_H-M   I4(1)/acd

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-y+1/4, x+3/4, z+1/4'
'y+1/4, -x+1/4, z+3/4'
'-x+1/2, y, -z'
'x, -y, -z+1/2'
'y+1/4, x+3/4, -z+3/4'
'-y+1/4, -x+1/4, -z+1/4'
'x+1/2, y+1/2, z+1/2'
'-x+1, -y+1/2, z+1'
'-y+3/4, x+5/4, z+3/4'
'y+3/4, -x+3/4, z+5/4'
'-x+1, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z+1'
'y+3/4, x+5/4, -z+5/4'
'-y+3/4, -x+3/4, -z+3/4'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'y-1/4, -x-3/4, -z-1/4'
'-y-1/4, x-1/4, -z-3/4'
'x-1/2, -y, z'
'-x, y, z-1/2'
'-y-1/4, -x-3/4, z-3/4'
'y-1/4, x-1/4, z-1/4'
'-x+1/2, -y+1/2, -z+1/2'
'x, y+1/2, -z'
'y+1/4, -x-1/4, -z+1/4'
'-y+1/4, x+1/4, -z-1/4'
'x, -y+1/2, z+1/2'
'-x+1/2, y+1/2, z'
'-y+1/4, -x-1/4, z-1/4'
'y+1/4, x+1/4, z+1/4'

_cell_length_a                   12.7276(18)
_cell_length_b                   12.7276(18)
_cell_length_c                   56.994(11)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     9233(3)
_cell_formula_units_Z            8
_cell_measurement_temperature    173(2)
_cell_measurement_reflns_used    1523
_cell_measurement_theta_min      2.17
_cell_measurement_theta_max      27.48

_exptl_crystal_description       colorless
_exptl_crystal_colour            plate
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.47
_exptl_crystal_size_min          0.19
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.164
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             3376
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9610
_exptl_absorpt_correction_T_max  0.9849
_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            3944
_diffrn_reflns_av_R_equivalents  0.0199
_diffrn_reflns_av_sigmaI/netI    0.0629
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_l_min       -67
_diffrn_reflns_limit_l_max       61
_diffrn_reflns_theta_min         1.43
_diffrn_reflns_theta_max         25.00
_reflns_number_total             2046
_reflns_number_gt                1290
_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)+(0.0480P)²+0.0000P] 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         2046
_refine_ls_number_parameters     138
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0800
_refine_ls_R_factor_gt           0.0428
_refine_ls_wR_factor_ref         0.0989
_refine_ls_wR_factor_gt          0.0919
_refine_ls_goodness_of_fit_ref   0.893
_refine_ls_restrained_S_all      0.893
_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
O2 O 0.13954(11) 0.47989(10) 0.06256(2) 0.0504(4) Uani 1 1 d . . .
H2A H 0.0920 0.4925 0.0527 0.076 Uiso 1 1 calc R . .
O1 O 0.13938(12) 0.32252(11) 0.04519(2) 0.0529(4) Uani 1 1 d . . .
C2 C 0.41269(14) 0.28995(13) 0.10838(3) 0.0274(4) Uani 1 1 d . . .
C1 C 0.5000 0.2500 0.1250 0.0267(8) Uani 1 4 d S . .
C5 C 0.25873(15) 0.35345(14) 0.07635(3) 0.0322(5) Uani 1 1 d . . .
C7 C 0.37365(14) 0.22085(13) 0.09142(3) 0.0310(5) Uani 1 1 d . . .
H7A H 0.4007 0.1514 0.0906 0.037 Uiso 1 1 calc R . .
C4 C 0.29828(15) 0.42331(15) 0.09266(3) 0.0363(5) Uani 1 1 d . . .
H4A H 0.2729 0.4935 0.0930 0.044 Uiso 1 1 calc R . .
C6 C 0.29728(14) 0.25125(16) 0.07591(3) 0.0318(4) Uani 1 1 d . . .
H6A H 0.2706 0.2024 0.0648 0.038 Uiso 1 1 calc R . .
C8 C 0.17370(15) 0.38286(16) 0.05968(4) 0.0389(5) Uani 1 1 d . . .
C3 C 0.37471(15) 0.39208(14) 0.10856(3) 0.0326(5) Uani 1 1 d . . .
H3A H 0.4013 0.4411 0.1197 0.039 Uiso 1 1 calc R . .
N1 N 0.02598(13) -0.00851(15) 0.03638(3) 0.0481(5) Uani 1 1 d . . .
C12 C 0.17556(16) 0.07841(17) 0.02045(3) 0.0421(5) Uani 1 1 d . . .
H12A H 0.2172 0.1402 0.0196 0.050 Uiso 1 1 calc R . .
C13 C 0.08760(17) 0.07596(17) 0.03435(4) 0.0482(6) Uani 1 1 d . . .
H13A H 0.0696 0.1373 0.0430 0.058 Uiso 1 1 calc R . .
C11 C 0.20303(14) -0.01000(16) 0.00770(3) 0.0373(5) Uani 1 1 d . . .
C10 C 0.13925(17) -0.09819(17) 0.00983(4) 0.0503(6) Uani 1 1 d . . .
H10A H 0.1551 -0.1608 0.0015 0.060 Uiso 1 1 calc R . .
C9 C 0.05271(18) -0.09294(17) 0.02424(4) 0.0526(6) Uani 1 1 d . . .
H9A H 0.0096 -0.1536 0.0256 0.063 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
O2 C8 1.320(2) . ?
O2 H2A 0.8400 . ?
O1 C8 1.209(2) . ?
C2 C3 1.387(2) . ?
C2 C7 1.398(2) . ?
C2 C1 1.5461(18) . ?
C1 C2 1.5461(18) 27_565 ?
C1 C2 1.5461(18) 20_656 ?
C1 C2 1.5461(18) 10_554 ?
C5 C4 1.381(2) . ?
C5 C6 1.390(3) . ?
C5 C8 1.488(3) . ?
C7 C6 1.370(2) . ?
C7 H7A 0.9500 . ?
C4 C3 1.387(2) . ?
C4 H4A 0.9500 . ?
C6 H6A 0.9500 . ?
C3 H3A 0.9500 . ?
N1 C9 1.323(3) . ?
N1 C13 1.336(3) . ?
C12 C13 1.372(3) . ?
C12 C11 1.384(3) . ?
C12 H12A 0.9500 . ?
C13 H13A 0.9500 . ?
C11 C10 1.391(3) . ?
C11 C11 1.484(3) 5 ?
C10 C9 1.376(3) . ?
C10 H10A 0.9500 . ?
C9 H9A 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 . . ?
C3 C2 C7 118.07(16) . . ?
C3 C2 C1 123.67(14) . . ?
C7 C2 C1 118.17(13) . . ?
C2 C1 C2 112.04(7) 27_565 . ?
C2 C1 C2 104.44(13) 27_565 20_656 ?
C2 C1 C2 112.04(7) . 20_656 ?
C2 C1 C2 112.04(7) 27_565 10_554 ?
C2 C1 C2 104.44(13) . 10_554 ?
C2 C1 C2 112.04(7) 20_656 10_554 ?
C4 C5 C6 119.07(17) . . ?
C4 C5 C8 122.20(17) . . ?
C6 C5 C8 118.70(16) . . ?
C6 C7 C2 121.38(16) . . ?
C6 C7 H7A 119.3 . . ?
C2 C7 H7A 119.3 . . ?
C5 C4 C3 120.69(17) . . ?
C5 C4 H4A 119.7 . . ?
C3 C4 H4A 119.7 . . ?
C7 C6 C5 120.20(17) . . ?
C7 C6 H6A 119.9 . . ?
C5 C6 H6A 119.9 . . ?
O1 C8 O2 124.08(18) . . ?
O1 C8 C5 122.62(18) . . ?
O2 C8 C5 113.30(17) . . ?
C2 C3 C4 120.55(17) . . ?
C2 C3 H3A 119.7 . . ?
C4 C3 H3A 119.7 . . ?
C9 N1 C13 117.23(18) . . ?
C13 C12 C11 119.4(2) . . ?
C13 C12 H12A 120.3 . . ?
C11 C12 H12A 120.3 . . ?
N1 C13 C12 123.2(2) . . ?
N1 C13 H13A 118.4 . . ?
C12 C13 H13A 118.4 . . ?
C12 C11 C10 117.59(17) . . ?
C12 C11 C11 120.94(13) . 5 ?
C10 C11 C11 121.47(13) . 5 ?
C9 C10 C11 118.7(2) . . ?
C9 C10 H10A 120.7 . . ?
C11 C10 H10A 120.7 . . ?
N1 C9 C10 123.9(2) . . ?
N1 C9 H9A 118.0 . . ?
C10 C9 H9A 118.0 . . ?

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
C3 C2 C1 C2 -0.32(17) . . . 27_565 ?
C7 C2 C1 C2 176.23(15) . . . 27_565 ?
C3 C2 C1 C2 116.7(2) . . . 20_656 ?
C7 C2 C1 C2 -66.75(10) . . . 20_656 ?
C3 C2 C1 C2 -121.82(19) . . . 10_554 ?
C7 C2 C1 C2 54.74(12) . . . 10_554 ?
C3 C2 C7 C6 -2.4(3) . . . . ?
C1 C2 C7 C6 -179.16(14) . . . . ?
C6 C5 C4 C3 -0.6(3) . . . . ?
C8 C5 C4 C3 177.47(18) . . . . ?
C2 C7 C6 C5 1.8(3) . . . . ?
C4 C5 C6 C7 -0.2(3) . . . . ?
C8 C5 C6 C7 -178.35(17) . . . . ?
C4 C5 C8 O1 179.21(19) . . . . ?
C6 C5 C8 O1 -2.7(3) . . . . ?
C4 C5 C8 O2 -1.5(3) . . . . ?
C6 C5 C8 O2 176.53(17) . . . . ?
C7 C2 C3 C4 1.6(3) . . . . ?
C1 C2 C3 C4 178.13(14) . . . . ?
C5 C4 C3 C2 -0.1(3) . . . . ?
C9 N1 C13 C12 0.1(3) . . . . ?
C11 C12 C13 N1 0.2(3) . . . . ?
C13 C12 C11 C10 -0.4(3) . . . . ?
C13 C12 C11 C11 179.4(2) . . . 5 ?
C12 C11 C10 C9 0.3(3) . . . . ?
C11 C11 C10 C9 -179.4(2) 5 . . . ?
C13 N1 C9 C10 -0.1(3) . . . . ?
C11 C10 C9 N1 -0.1(3) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
O2 H2A N1 0.84 1.78 2.607(2) 168.3 10_454

_diffrn_measured_fraction_theta_max 1.000
_diffrn_reflns_theta_full        25.00
_diffrn_measured_fraction_theta_full 1.000
_refine_diff_density_max         0.189
_refine_diff_density_min         -0.157
_refine_diff_density_rms         0.035

# SQUEEZE RESULTS (APPEND TO CIF)
# Note: Data are Listed for all Voids in the P1 Unit Cell
# i.e. Centre of Gravity, Solvent Accessible Volume,
# Recovered number of Electrons in the Void and
# Details about the Squeezed Material
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
_platon_squeeze_void_content
1 0.000 0.250 0.125 183 44 ' '
2 0.000 0.750 0.375 183 44 ' '
3 0.000 0.250 0.625 183 44 ' '
4 0.000 0.750 0.875 183 44 ' '
5 0.500 0.750 0.125 183 44 ' '
6 0.500 0.250 0.375 183 44 ' '
7 0.500 0.750 0.625 183 44 ' '
8 0.500 0.250 0.875 183 44 ' '
_platon_squeeze_details          
;
;

