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