# Supplementary Material (ESI) for New Journal of Chemistry
# This journal is © The Royal Society of Chemistry and 
# The Centre National de la Recherche Scientifique, 2009

data_global

_journal_coden_Cambridge         440
_journal_volume                  ?
_journal_page_first              ?
_journal_year                    ?

loop_
_publ_author_name
'Roger Bishop'
'Isa Y. H. Chan'
'Donald C. Craig'
'Vi T. Nguyen'
'Marcia Scudder'

_publ_contact_author_name        'Roger Bishop'
_publ_contact_author_email       R.BISHOP@UNSW.EDU.AU

_publ_section_title              
;
Crystallisation of C2-symmetric bicyclo[3.3.1]nonane-endo-2,endo-6-diols:
supramolecular synthons and concomitant degrees of enantiomer separation

;

# Attachment 'drb198-1.cif'

data_drb198
_database_code_depnum_ccdc_archive 'CCDC 726704'
_audit_creation_method           'RAELSPUB and manual entry'

# CHEMICAL DATA

_chemical_name_systematic        ?
_chemical_formula_moiety         'C9 H16 O2'
_chemical_formula_sum            'C9 H16 O2'
_chemical_formula_iupac          ?
_chemical_formula_weight         156.2

# CRYSTAL DATA

_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_H-M   'P 41 21 2'
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 x,y,z
2 -x,-y,1/2+z
3 1/2-y,1/2+x,1/4+z
4 1/2+y,1/2-x,3/4+z
5 y,x,-z
6 -y,-x,1/2-z
7 1/2-x,1/2+y,1/4-z
8 1/2+x,1/2-y,3/4-z

_cell_length_a                   9.891(1)
_cell_length_b                   9.891(1)
_cell_length_c                   17.167(5)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1679.5(5)
_cell_formula_units_Z            8
_cell_measurement_reflns_used    10
_cell_measurement_theta_min      20
_cell_measurement_theta_max      25
_cell_measurement_temperature    294
_exptl_crystal_description       irregular
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          ?
_exptl_crystal_size_mid          ?
_exptl_crystal_size_min          ?
_exptl_crystal_size_rad          0.1
_exptl_crystal_density_diffrn    1.24
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             688.0
_exptl_absorpt_coefficient_mu    0.645
_exptl_absorpt_correction_type   none
_exptl_absorpt_process_details   ?
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?

# EXPERIMENTAL DATA

_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_measurement_device_type  'Nonius CAD-4'
_diffrn_measurement_method       \w--2\q
_diffrn_reflns_number            1443
_diffrn_reflns_av_R_equivalents  0.018
_diffrn_reflns_theta_max         60
_diffrn_measured_fraction_theta_max 1.00
_diffrn_reflns_theta_full        60
_diffrn_measured_fraction_theta_full 1.00
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_limit_l_max       19
_diffrn_standards_number         1
_diffrn_standards_interval_time  30
_diffrn_standards_decay_%        0

# REFINEMENT DATA

_refine_special_details          ?
_reflns_number_total             1246
_reflns_number_gt                967
_reflns_threshold_expression     I>2\s(I)
_refine_ls_structure_factor_coef F
_refine_ls_R_factor_gt           0.040
_refine_ls_wR_factor_ref         0.056
_refine_ls_abs_structure_Flack   ?
_refine_ls_hydrogen_treatment    noref
_refine_ls_number_reflns         1152
_refine_ls_number_parameters     100
_refine_ls_goodness_of_fit_ref   1.41
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     'w = 1/[\s^2^(F) + 0.0004F^2^]'
_refine_ls_shift/su_max          0.003
_refine_diff_density_max         0.19
_refine_diff_density_min         -0.24
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       ?
_atom_type_scat_source           
'International Tables for X-ray Crystallography, Vol. IV'

# ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS

loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_type_symbol
_atom_site_occupancy
O1 0.19501(18) 0.51732(16) 0.71858(9) 0.0658(6) Uani O 1.0
O2 0.31549(17) -0.03363(15) 0.69193(8) 0.0645(6) Uani O 1.0
C1 0.1619(2) 0.3188(3) 0.8003(1) 0.0523(6) Uani C 1.0
C2 0.2628(2) 0.4146(2) 0.7620(1) 0.0531(6) Uani C 1.0
C3 0.3705(2) 0.3454(2) 0.7134(1) 0.0528(6) Uani C 1.0
C4 0.4322(2) 0.2230(3) 0.7553(1) 0.0565(7) Uani C 1.0
C5 0.3309(2) 0.1327(2) 0.7971(1) 0.0489(6) Uani C 1.0
C6 0.2392(2) 0.0485(2) 0.7441(1) 0.0507(6) Uani C 1.0
C7 0.1404(2) 0.1310(2) 0.6970(1) 0.0590(7) Uani C 1.0
C8 0.0700(2) 0.2420(3) 0.7451(2) 0.0633(7) Uani C 1.0
C9 0.2419(2) 0.2187(3) 0.8503(1) 0.0589(7) Uani C 1.0
H1O1 0.1913 0.4991 0.6613 0.066 Uani H 1.0
H1O2 0.3760 -0.0920 0.7243 0.064 Uani H 1.0
HC1 0.1034 0.3734 0.8359 0.052 Uani H 1.0
HC2 0.3113 0.4616 0.8053 0.053 Uani H 1.0
H1C3 0.4440 0.4119 0.7019 0.053 Uani H 1.0
H2C3 0.3288 0.3142 0.6634 0.053 Uani H 1.0
H1C4 0.4983 0.2573 0.7948 0.056 Uani H 1.0
H2C4 0.4807 0.1669 0.7158 0.056 Uani H 1.0
HC5 0.3830 0.0687 0.8308 0.049 Uani H 1.0
HC6 0.1855 -0.0134 0.7782 0.051 Uani H 1.0
H1C7 0.0697 0.0690 0.6756 0.059 Uani H 1.0
H2C7 0.1903 0.1748 0.6531 0.059 Uani H 1.0
H1C8 -0.0032 0.1986 0.7765 0.063 Uani H 1.0
H2C8 0.0292 0.3085 0.7080 0.063 Uani H 1.0
H1C9 0.1780 0.1590 0.8795 0.059 Uani H 1.0
H2C9 0.2999 0.2693 0.8880 0.059 Uani H 1.0

loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_12
_atom_site_aniso_U_13
_atom_site_aniso_U_23
_atom_site_aniso_type_symbol
O1 0.090(1) 0.0514(9) 0.0555(9) 0.026(1) 0.0078(9) 0.0011(8) O
O2 0.082(1) 0.060(1) 0.0518(9) 0.026(1) -0.0137(9) -0.0105(8) O
C1 0.056(1) 0.058(1) 0.044(1) 0.012(1) 0.013(1) -0.004(1) C
C2 0.061(2) 0.050(1) 0.048(1) 0.009(1) -0.001(1) -0.009(1) C
C3 0.048(1) 0.051(1) 0.059(1) 0.001(1) 0.010(1) 0.001(1) C
C4 0.041(1) 0.068(2) 0.060(1) 0.007(1) -0.004(1) 0.001(1) C
C5 0.053(1) 0.058(2) 0.036(1) 0.012(1) -0.007(1) 0.003(1) C
C6 0.054(1) 0.049(1) 0.049(1) 0.005(1) -0.002(1) 0.003(1) C
C7 0.051(1) 0.054(1) 0.072(2) 0.006(1) -0.018(1) -0.012(1) C
C8 0.042(1) 0.065(2) 0.083(2) 0.009(1) -0.003(1) -0.008(2) C
C9 0.075(2) 0.065(2) 0.037(1) 0.016(1) 0.005(1) 0.001(1) C

# MOLECULAR GEOMETRY

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C2 1.428(3) 1_555 1_555 no
O2 C6 1.425(3) 1_555 1_555 no
C1 C2 1.526(3) 1_555 1_555 no
C1 C8 1.518(3) 1_555 1_555 no
C1 C9 1.531(3) 1_555 1_555 no
C2 C3 1.516(3) 1_555 1_555 no
C3 C4 1.535(3) 1_555 1_555 no
C4 C5 1.522(3) 1_555 1_555 no
C5 C6 1.531(3) 1_555 1_555 no
C5 C9 1.527(3) 1_555 1_555 no
C6 C7 1.509(3) 1_555 1_555 no
C7 C8 1.539(3) 1_555 1_555 no

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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C2 C1 C8 115.6(2) 1_555 1_555 1_555 no
C2 C1 C9 107.7(2) 1_555 1_555 1_555 no
C8 C1 C9 109.7(2) 1_555 1_555 1_555 no
O1 C2 C1 111.1(2) 1_555 1_555 1_555 no
O1 C2 C3 111.3(2) 1_555 1_555 1_555 no
C1 C2 C3 114.7(2) 1_555 1_555 1_555 no
C2 C3 C4 112.1(2) 1_555 1_555 1_555 no
C3 C4 C5 115.0(2) 1_555 1_555 1_555 no
C4 C5 C6 115.4(2) 1_555 1_555 1_555 no
C4 C5 C9 109.5(2) 1_555 1_555 1_555 no
C6 C5 C9 108.5(2) 1_555 1_555 1_555 no
O2 C6 C5 111.7(2) 1_555 1_555 1_555 no
O2 C6 C7 108.3(2) 1_555 1_555 1_555 no
C5 C6 C7 114.1(2) 1_555 1_555 1_555 no
C6 C7 C8 113.1(2) 1_555 1_555 1_555 no
C1 C8 C7 114.9(2) 1_555 1_555 1_555 no
C1 C9 C5 108.9(2) 1_555 1_555 1_555 no

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
C8 C1 C2 O1 61.1(2) 1_555 1_555 1_555 1_555 no
C8 C1 C2 C3 -66.2(3) 1_555 1_555 1_555 1_555 no
C9 C1 C2 O1 -175.9(2) 1_555 1_555 1_555 1_555 no
C9 C1 C2 C3 56.8(2) 1_555 1_555 1_555 1_555 no
C2 C1 C8 C7 71.0(3) 1_555 1_555 1_555 1_555 no
C9 C1 C8 C7 -51.0(3) 1_555 1_555 1_555 1_555 no
C2 C1 C9 C5 -64.5(2) 1_555 1_555 1_555 1_555 no
C8 C1 C9 C5 62.1(2) 1_555 1_555 1_555 1_555 no
O1 C2 C3 C4 -172.8(2) 1_555 1_555 1_555 1_555 no
C1 C2 C3 C4 -45.6(3) 1_555 1_555 1_555 1_555 no
C2 C3 C4 C5 42.8(3) 1_555 1_555 1_555 1_555 no
C3 C4 C5 C6 71.0(3) 1_555 1_555 1_555 1_555 no
C3 C4 C5 C9 -51.7(2) 1_555 1_555 1_555 1_555 no
C4 C5 C6 O2 56.0(2) 1_555 1_555 1_555 1_555 no
C4 C5 C6 C7 -67.3(3) 1_555 1_555 1_555 1_555 no
C9 C5 C6 O2 179.3(2) 1_555 1_555 1_555 1_555 no
C9 C5 C6 C7 56.0(2) 1_555 1_555 1_555 1_555 no
C4 C5 C9 C1 62.5(2) 1_555 1_555 1_555 1_555 no
C6 C5 C9 C1 -64.3(2) 1_555 1_555 1_555 1_555 no
O2 C6 C7 C8 -169.7(2) 1_555 1_555 1_555 1_555 no
C5 C6 C7 C8 -44.6(3) 1_555 1_555 1_555 1_555 no
C6 C7 C8 C1 42.3(3) 1_555 1_555 1_555 1_555 no