Electronic Supplementary Material for CrystEngComm
This journal is (c) The Royal Society of Chemistry 2006

data_global
_journal_name_full               CrystEngComm

_journal_coden_Cambridge         1350

_publ_contact_author_name        'George Shimizu'
_publ_contact_author_address     
;
Department of Chemistry
University of Calgary
2500 University Drive NW
Calgary
Alberta
T2N 1N4
CANADA
;

_publ_contact_author_email       GSHIMIZU@UCALGARY.CA

_publ_section_title              
;
An adamantane-based tetraphosphonic acid that forms an
open diamondoid net via a hydrogen-bonded phosphonic acid-water cluster
;
loop_
_publ_author_name
'George Shimizu'
'Brett D. Chandler'
'Katherine M. E. Jones'
'Amir H. Mahmoudkhani'

# Attachment 'Shimizu AdamantanePO3H2.cif'

data_import
_database_code_depnum_ccdc_archive 'CCDC 290377'

_audit_creation_method           SHELXL-97
_chemical_name_systematic        
;1,3,5,7-tetrakis(4-Phosphonophenyl)adamantane
bis-chloroform solvate tetrahydrate
;
_chemical_name_common            
;
1,3,5,7-tetrakis(4-Phosphonophenyl)adamantane bis-chloroform
solvate tetrahydrate
;
_chemical_melting_point          ?
_chemical_formula_moiety         'C34 H36 O12 P4, 2(C H Cl3), 4(H2 O)'
_chemical_formula_sum            'C36 H46 Cl6 O16 P4'
_chemical_formula_weight         1071.31

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'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
P P 0.1023 0.0942 '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'

_symmetry_cell_setting           tetragonal
_symmetry_space_group_name_H-M   'P -4'
_symmetry_int_tables_number      81

loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, z'
'y, -x, -z'
'-y, x, -z'

_cell_length_a                   12.4153(18)
_cell_length_b                   12.4153(18)
_cell_length_c                   7.3494(15)
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_volume                     1132.8(3)
_cell_formula_units_Z            1
_cell_measurement_temperature    293(2)
_cell_measurement_reflns_used    1129
_cell_measurement_theta_min      0.998
_cell_measurement_theta_max      27.485

_exptl_crystal_description       Block
_exptl_crystal_colour            Clear
_exptl_crystal_size_max          0.293
_exptl_crystal_size_mid          0.207
_exptl_crystal_size_min          0.184
_exptl_crystal_density_meas      ?
_exptl_crystal_density_diffrn    1.573
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             554
_exptl_absorpt_coefficient_mu    0.589
_exptl_absorpt_correction_type   none
_exptl_absorpt_correction_T_min  ?
_exptl_absorpt_correction_T_max  ?
_exptl_absorpt_process_details   ?

_exptl_special_details           
;
?
;

_diffrn_ambient_temperature      273
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  KappaCCD
_diffrn_measurement_method       'CCD rotation images, thick slices'
_diffrn_detector_area_resol_mean 9
_diffrn_standards_number         ?
_diffrn_standards_interval_count ?
_diffrn_standards_interval_time  ?
_diffrn_standards_decay_%        ?
_diffrn_reflns_number            3800
_diffrn_reflns_av_R_equivalents  0.0390
_diffrn_reflns_av_sigmaI/netI    0.0416
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_theta_min         1.64
_diffrn_reflns_theta_max         27.49
_reflns_number_total             2168
_reflns_number_gt                1961
_reflns_threshold_expression     >2sigma(I)

_computing_data_collection       'Collect (Nonius BV, 1997-2000)'
_computing_cell_refinement       'HKL Scalepack (Otwinowski & Minor 1997)'
_computing_data_reduction        'HKL Denzo and Scalepack'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_molecular_graphics    ?
_computing_publication_material  ?

_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^)+(0.0572P)^2^+1.5945P] 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_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.26(13)
_refine_ls_number_reflns         2168
_refine_ls_number_parameters     156
_refine_ls_number_restraints     10
_refine_ls_R_factor_all          0.0556
_refine_ls_R_factor_gt           0.0471
_refine_ls_wR_factor_ref         0.1236
_refine_ls_wR_factor_gt          0.1140
_refine_ls_goodness_of_fit_ref   1.075
_refine_ls_restrained_S_all      1.089
_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
C1 C 0.6692(3) 0.1770(3) 0.3884(5) 0.0207(8) Uani 1 1 d . . .
H1 H 0.6571 0.1031 0.3937 0.025 Uiso 1 1 calc R . .
C2 C 0.7422(3) 0.2244(3) 0.5076(5) 0.0185(7) Uani 1 1 d . . .
C3 C 0.7602(3) 0.3361(3) 0.4971(5) 0.0211(8) Uani 1 1 d . . .
H3 H 0.8093 0.3689 0.5750 0.025 Uiso 1 1 calc R . .
C4 C 0.7048(3) 0.3968(3) 0.3710(5) 0.0198(8) Uani 1 1 d . . .
H4 H 0.7173 0.4705 0.3648 0.024 Uiso 1 1 calc R . .
C5 C 0.6300(3) 0.3502(3) 0.2517(5) 0.0148(7) Uani 1 1 d . . .
C6 C 0.6146(3) 0.2391(3) 0.2617(5) 0.0188(8) Uani 1 1 d . . .
H6 H 0.5667 0.2060 0.1819 0.023 Uiso 1 1 calc R . .
C7 C 0.4871(3) 0.3579(3) 0.0011(5) 0.0146(7) Uani 1 1 d . . .
H7A H 0.5271 0.3074 -0.0735 0.018 Uiso 1 1 calc R . .
H7B H 0.4382 0.3171 0.0775 0.018 Uiso 1 1 calc R . .
C8 C 0.5660(3) 0.4222(3) 0.1219(4) 0.0126(7) Uani 1 1 d . . .
C9 C 0.5000 0.5000 0.2409(6) 0.0132(9) Uani 1 2 d S . .
H9A H 0.5482 0.5409 0.3184 0.016 Uiso 0.50 1 calc PR . .
H9B H 0.4518 0.4591 0.3184 0.016 Uiso 0.50 1 calc PR . .
O1 O 0.7682(2) 0.1797(2) 0.8587(4) 0.0284(6) Uani 1 1 d . . .
O2 O 0.8032(2) 0.0289(2) 0.6322(4) 0.0286(7) Uani 1 1 d . . .
O3 O 0.9330(2) 0.1870(2) 0.6706(4) 0.0284(6) Uani 1 1 d . . .
O4 O 0.8860(3) 0.1140(3) 1.1135(4) 0.0366(8) Uani 1 1 d D . .
P1 P 0.81457(8) 0.14710(8) 0.67107(13) 0.0206(2) Uani 1 1 d . . .
C10 C 0.4775(7) -0.0313(7) -0.0940(12) 0.038(2) Uani 0.50 1 d PD . .
Cl1 Cl 0.39664(12) 0.05473(11) 0.0263(2) 0.0568(4) Uani 1 1 d D . .
Cl2 Cl 0.5000 0.0000 -0.3116(3) 0.0923(10) Uani 1 2 d SD . .
H50 H 0.926(3) 0.151(3) 1.184(5) 0.020 Uiso 1 1 d D . .
H51 H 0.860(3) 0.0498(19) 1.131(5) 0.020 Uiso 1 1 d D . .
H1A H 0.8259 0.1529 0.9900 0.024 Uiso 1 1 d . . .
H3A H 0.9725 0.1836 0.5658 0.024 Uiso 1 1 d . . .
H53 H 0.444(3) -0.1050(14) -0.105(6) 0.020 Uiso 0.50 1 d PD . .

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 0.0227(19) 0.0160(17) 0.0235(18) 0.0034(15) -0.0018(15) 0.0007(14)
C2 0.0192(17) 0.0215(17) 0.0148(15) 0.0027(15) -0.0031(14) 0.0034(13)
C3 0.0239(18) 0.0231(18) 0.0162(17) 0.0001(15) -0.0065(16) -0.0010(14)
C4 0.0253(19) 0.0150(16) 0.0190(17) 0.0013(14) -0.0036(15) -0.0021(14)
C5 0.0152(17) 0.0151(16) 0.0142(15) 0.0020(14) -0.0021(14) 0.0029(13)
C6 0.0221(19) 0.0171(18) 0.0172(17) -0.0003(14) -0.0054(15) -0.0036(14)
C7 0.0178(16) 0.0148(16) 0.0112(15) -0.0013(13) 0.0002(14) 0.0005(13)
C8 0.0162(16) 0.0129(16) 0.0088(15) -0.0009(12) -0.0019(13) 0.0016(12)
C9 0.014(2) 0.016(2) 0.009(2) 0.000 0.000 0.000(2)
O1 0.0317(16) 0.0360(16) 0.0174(14) 0.0009(12) -0.0009(12) 0.0062(12)
O2 0.0390(16) 0.0214(14) 0.0255(15) 0.0047(12) -0.0065(13) 0.0051(12)
O3 0.0182(13) 0.0442(18) 0.0229(14) 0.0044(14) -0.0056(12) 0.0015(11)
O4 0.0450(19) 0.0359(18) 0.0290(16) 0.0083(14) -0.0187(15) -0.0106(15)
P1 0.0229(5) 0.0232(5) 0.0156(4) 0.0035(4) -0.0042(4) 0.0034(4)
C10 0.042(5) 0.025(5) 0.047(5) -0.001(4) 0.003(4) -0.018(4)
Cl1 0.0597(8) 0.0495(8) 0.0612(9) -0.0204(7) 0.0129(7) -0.0064(6)
Cl2 0.0676(15) 0.163(3) 0.0461(12) 0.000 0.000 0.0476(17)

_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 C6 1.386(5) . ?
C1 C2 1.391(5) . ?
C1 H1 0.9300 . ?
C2 C3 1.407(5) . ?
C2 P1 1.781(4) . ?
C3 C4 1.379(5) . ?
C3 H3 0.9300 . ?
C4 C5 1.401(5) . ?
C4 H4 0.9300 . ?
C5 C6 1.395(5) . ?
C5 C8 1.530(5) . ?
C6 H6 0.9300 . ?
C7 C8 1.536(5) 3_565 ?
C7 C8 1.545(4) . ?
C7 H7A 0.9700 . ?
C7 H7B 0.9700 . ?
C8 C7 1.536(5) 4_655 ?
C8 C9 1.539(4) . ?
C9 C8 1.539(4) 2_665 ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
O1 P1 1.548(3) . ?
O1 H1A 1.247(3) . ?
O2 P1 1.501(3) . ?
O3 P1 1.552(3) . ?
O3 H3A 0.914(3) . ?
O4 H50 0.853(18) . ?
O4 H51 0.868(18) . ?
O4 H1A 1.270(3) . ?
C10 C10 0.957(16) 2_655 ?
C10 Cl2 1.669(9) . ?
C10 Cl1 1.712(9) . ?
C10 Cl1 1.819(10) 2_655 ?
C10 H53 0.992(16) . ?
Cl1 C10 1.819(10) 2_655 ?
Cl2 C10 1.669(9) 2_655 ?

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
C6 C1 C2 120.4(3) . . ?
C6 C1 H1 119.8 . . ?
C2 C1 H1 119.8 . . ?
C1 C2 C3 119.1(3) . . ?
C1 C2 P1 121.7(3) . . ?
C3 C2 P1 119.2(3) . . ?
C4 C3 C2 119.7(3) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
C3 C4 C5 121.7(3) . . ?
C3 C4 H4 119.1 . . ?
C5 C4 H4 119.1 . . ?
C6 C5 C4 117.8(3) . . ?
C6 C5 C8 122.6(3) . . ?
C4 C5 C8 119.5(3) . . ?
C1 C6 C5 121.2(3) . . ?
C1 C6 H6 119.4 . . ?
C5 C6 H6 119.4 . . ?
C8 C7 C8 110.7(3) 3_565 . ?
C8 C7 H7A 109.5 3_565 . ?
C8 C7 H7A 109.5 . . ?
C8 C7 H7B 109.5 3_565 . ?
C8 C7 H7B 109.5 . . ?
H7A C7 H7B 108.1 . . ?
C5 C8 C7 110.8(3) . 4_655 ?
C5 C8 C9 106.8(3) . . ?
C7 C8 C9 109.4(2) 4_655 . ?
C5 C8 C7 112.7(3) . . ?
C7 C8 C7 108.8(2) 4_655 . ?
C9 C8 C7 108.2(2) . . ?
C8 C9 C8 110.8(4) . 2_665 ?
C8 C9 H9A 109.5 . . ?
C8 C9 H9A 109.5 2_665 . ?
C8 C9 H9B 109.5 . . ?
C8 C9 H9B 109.5 2_665 . ?
H9A C9 H9B 108.1 . . ?
P1 O1 H1A 113.9(2) . . ?
P1 O3 H3A 119.6(2) . . ?
H50 O4 H51 128(3) . . ?
H50 O4 H1A 125(3) . . ?
H51 O4 H1A 104(3) . . ?
O2 P1 O1 112.93(17) . . ?
O2 P1 O3 113.65(17) . . ?
O1 P1 O3 105.72(17) . . ?
O2 P1 C2 110.52(17) . . ?
O1 P1 C2 105.81(17) . . ?
O3 P1 C2 107.74(17) . . ?
C10 C10 Cl2 73.3(3) 2_655 . ?
C10 C10 Cl1 80.5(9) 2_655 . ?
Cl2 C10 Cl1 116.6(5) . . ?
C10 C10 Cl1 68.2(9) 2_655 2_655 ?
Cl2 C10 Cl1 111.1(5) . 2_655 ?
Cl1 C10 Cl1 110.6(5) . 2_655 ?
C10 C10 H53 165.9(17) 2_655 . ?
Cl2 C10 H53 95.7(18) . . ?
Cl1 C10 H53 112.8(13) . . ?
Cl1 C10 H53 109(2) 2_655 . ?
C10 Cl1 C10 31.3(5) . 2_655 ?
C10 Cl2 C10 33.3(6) 2_655 . ?

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
C6 C1 C2 C3 -0.4(6) . . . . ?
C6 C1 C2 P1 -179.6(3) . . . . ?
C1 C2 C3 C4 0.7(5) . . . . ?
P1 C2 C3 C4 179.9(3) . . . . ?
C2 C3 C4 C5 0.1(6) . . . . ?
C3 C4 C5 C6 -1.3(6) . . . . ?
C3 C4 C5 C8 176.5(3) . . . . ?
C2 C1 C6 C5 -0.8(6) . . . . ?
C4 C5 C6 C1 1.6(6) . . . . ?
C8 C5 C6 C1 -176.1(4) . . . . ?
C6 C5 C8 C7 -124.2(4) . . . 4_655 ?
C4 C5 C8 C7 58.1(4) . . . 4_655 ?
C6 C5 C8 C9 116.7(3) . . . . ?
C4 C5 C8 C9 -61.0(4) . . . . ?
C6 C5 C8 C7 -2.1(5) . . . . ?
C4 C5 C8 C7 -179.7(3) . . . . ?
C8 C7 C8 C5 178.1(3) 3_565 . . . ?
C8 C7 C8 C7 -58.6(3) 3_565 . . 4_655 ?
C8 C7 C8 C9 60.2(3) 3_565 . . . ?
C5 C8 C9 C8 178.9(3) . . . 2_665 ?
C7 C8 C9 C8 59.0(2) 4_655 . . 2_665 ?
C7 C8 C9 C8 -59.5(2) . . . 2_665 ?
C1 C2 P1 O2 12.1(4) . . . . ?
C3 C2 P1 O2 -167.1(3) . . . . ?
C1 C2 P1 O1 -110.5(3) . . . . ?
C3 C2 P1 O1 70.4(3) . . . . ?
C1 C2 P1 O3 136.8(3) . . . . ?
C3 C2 P1 O3 -42.4(3) . . . . ?
Cl2 C10 Cl1 C10 -65.9(6) . . . 2_655 ?
Cl1 C10 Cl1 C10 62.3(6) 2_655 . . 2_655 ?
Cl1 C10 Cl2 C10 70.0(10) . . . 2_655 ?
Cl1 C10 Cl2 C10 -57.9(9) 2_655 . . 2_655 ?

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
O4 H50 O2 0.853(18) 1.94(2) 2.775(4) 165(4) 3_667
O4 H51 O3 0.868(18) 2.14(3) 2.896(4) 146(4) 4_647
O1 H1A O4 1.247(3) 1.270(3) 2.512(4) 172.6(2) .
O3 H3A O2 0.914(3) 1.623(3) 2.527(4) 169.2(2) 3_666

_diffrn_measured_fraction_theta_max 0.985
_diffrn_reflns_theta_full        27.49
_diffrn_measured_fraction_theta_full 0.985
_refine_diff_density_max         0.472
_refine_diff_density_min         -0.687
_refine_diff_density_rms         0.080


