data_global #=========================================================================== _audit_creation_date '2012-07-24' _audit_creation_method 'from SHELXTL CIF, local template and enCIFer' _audit_update_record ; ; #=========================================================================== # 1. SUBMISSION DETAILS #=========================================================================== _publ_contact_author_name 'Dr Damon A. Parrish' _publ_contact_author_address ; Laboratory for the Structure of Matter Naval Research Laboratory Washington, DC 20375 ; _publ_contact_author_email 'damon.parrish@nrl.navy.mil' _publ_contact_author_fax '202-767-6874' _publ_contact_author_phone '202-404-2141' _publ_requested_journal ? _publ_requested_category ? _publ_requested_coeditor_name ? _publ_contact_letter ; ; #=========================================================================== # 2. PROCESSING SUMMARY (IUCr Office Use Only) # Do NOT alter anthing in this section. #=========================================================================== _journal_date_recd_electronic ? _journal_date_to_coeditor ? _journal_date_from_coeditor ? _journal_date_accepted ? _journal_date_printers_first ? _journal_date_printers_final ? _journal_date_proofs_out ? _journal_date_proofs_in ? _journal_coeditor_name ? _journal_coeditor_code ? _journal_coeditor_notes ; ? ; _journal_techeditor_code ? _journal_techeditor_notes ; ? ; _journal_coden_ASTM ? _journal_name_full ? _journal_year ? _journal_volume ? _journal_issue ? _journal_page_first ? _journal_page_last ? _journal_suppl_publ_number ? _journal_suppl_publ_pages ? #=========================================================================== # 3. TITLE AND AUTHOR LIST #=========================================================================== _publ_section_title ; title ; loop_ _publ_author_name _publ_author_address _publ_author_footnote 'Parrish, Damon A.' ; CBMSE, Code 6910 Naval Research Laboratory Washington, DC 20375 ; ? 'Snow, Arthur' ; Chemistry Division, Code 6123 Naval Research Laboratory Washington, DC 20375 ; ? 'Rodig, Michael' ; Chemistry Division, Code 6123 Naval Research Laboratory Washington, DC 20375 ; ? #=========================================================================== # 4. TEXT #=========================================================================== _publ_section_abstract ; ; _publ_section_comment ; ; _publ_section_exptl_prep ; ; _publ_section_exptl_refinement ; ; _publ_section_references ; Bruker (2009). APEX2 v2010.3-0. Bruker AXS Inc., Madison, Wisconsin, USA. Bruker (2009). SAINT v7.68A. Bruker AXS Inc., Madison, Wisconsin, USA. Bruker (2008). SADABS v2008/1, Bruker AXS Inc., Madison, Wisconsin, USA. Bruker (2008). XPREP v2008/2. Bruker AXS Inc., Madison, Wisconsin, USA. Bruker (2008). SHELXTL v2008/4. Bruker AXS Inc., Madison, Wisconsin, USA. ; _publ_section_figure_captions ; ; _publ_section_table_legends ; ; _publ_section_acknowledgements ; Crystallographic studies were supported in part by the Office of Naval Research (ONR) and the Naval Research Laboratory (NRL). ; #========================================================================== data_snow001 _audit_creation_date '2012-07-24' _audit_creation_method 'from SHELXTL CIF, local template and enCIFer' _chemical_name_systematic ; 2,4,6-tris(chloromethyl)-1,3,5-trioxane ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C6 H9 Cl3 O3' _chemical_formula_sum 'C6 H9 Cl3 O3' _chemical_formula_weight 235.48 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' 'Cl' 'Cl' 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M P2(1)/n loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x-1/2, -y-1/2, z-1/2' _cell_length_a 8.2204(14) _cell_length_b 8.6550(15) _cell_length_c 13.295(2) _cell_angle_alpha 90.00 _cell_angle_beta 90.139(2) _cell_angle_gamma 90.00 _cell_volume 945.9(3) _cell_formula_units_Z 4 _cell_measurement_temperature 150(2) _cell_measurement_reflns_used ? _cell_measurement_theta_min ? _cell_measurement_theta_max ? _exptl_crystal_description prism _exptl_crystal_colour colorless _exptl_crystal_size_max 0.74 _exptl_crystal_size_mid 0.21 _exptl_crystal_size_min 0.12 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.653 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 480 _exptl_absorpt_coefficient_mu 0.933 _exptl_absorpt_correction_type 'multi-scan' _exptl_absorpt_process_details 'SADABS v2008/1 (Bruker, 2008)' _exptl_absorpt_correction_T_min 0.5452 _exptl_absorpt_correction_T_max 0.8963 _exptl_special_details ; ? ; _diffrn_ambient_temperature 150(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type 'MoK\a' _diffrn_radiation_source 'fine focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker SMART APEX II CCD' _diffrn_measurement_method '\w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 8454 _diffrn_reflns_av_R_equivalents 0.0259 _diffrn_reflns_av_sigmaI/netI 0.0209 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 2.81 _diffrn_reflns_theta_max 26.51 _reflns_number_total 1954 _reflns_number_gt 1794 _reflns_threshold_expression I>2\s(I) _computing_data_collection 'Bruker APEX2 v2010.3-0 (Bruker, 2009)' _computing_cell_refinement 'Bruker APEX2 v2010.3-0 (Bruker, 2009)' _computing_data_reduction ; Bruker SAINT v7.68A (Bruker, 2009), Bruker XPREP v2008/2 (Bruker, 2008) ; _computing_structure_solution 'Bruker SHELXTL v2008/4 (Bruker, 2008)' _computing_structure_refinement 'Bruker SHELXTL v2008/4 (Bruker, 2008)' _computing_molecular_graphics 'Bruker SHELXTL v2008/4 (Bruker, 2008)' _computing_publication_material 'Bruker SHELXTL v2008/4 (Bruker, 2008)' _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^)+(0.0280P)^2^+0.3798P] 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 constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 1954 _refine_ls_number_parameters 103 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0276 _refine_ls_R_factor_gt 0.0247 _refine_ls_wR_factor_ref 0.0630 _refine_ls_wR_factor_gt 0.0601 _refine_ls_goodness_of_fit_ref 1.074 _refine_ls_restrained_S_all 1.074 _refine_ls_shift/su_max 0.001 _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 0.84063(12) 0.36666(12) 0.71721(7) 0.0189(2) Uani 1 1 d . . . C2 C 0.71019(18) 0.35667(17) 0.64725(10) 0.0178(3) Uani 1 1 d . . . H2 H 0.6675 0.2486 0.6441 0.021 Uiso 1 1 calc R . . O3 O 0.58487(12) 0.46036(12) 0.67509(7) 0.0186(2) Uani 1 1 d . . . C4 C 0.52821(18) 0.42200(17) 0.77290(10) 0.0180(3) Uani 1 1 d . . . H4 H 0.4814 0.3154 0.7733 0.022 Uiso 1 1 calc R . . O5 O 0.65827(12) 0.43295(12) 0.84294(7) 0.0187(2) Uani 1 1 d . . . C6 C 0.78347(18) 0.32928(17) 0.81492(10) 0.0180(3) Uani 1 1 d . . . H6 H 0.7433 0.2203 0.8170 0.022 Uiso 1 1 calc R . . C7 C 0.76965(19) 0.40728(18) 0.54537(11) 0.0216(3) Uani 1 1 d . . . H7A H 0.8219 0.5100 0.5509 0.026 Uiso 1 1 calc R . . H7B H 0.6763 0.4163 0.4985 0.026 Uiso 1 1 calc R . . Cl8 Cl 0.91233(5) 0.27080(5) 0.49727(3) 0.03035(12) Uani 1 1 d . . . C9 C 0.40243(5) 0.53761(5) 0.80551(3) 0.0223(3) Uani 1 1 d . . . H9A H 0.4483 0.6432 0.8016 0.027 Uiso 1 1 calc R . . H9B H 0.3711 0.5175 0.8762 0.027 Uiso 1 1 calc R . . Cl10 Cl 0.22770(5) 0.52371(5) 0.72634(3) 0.03355(13) Uani 1 1 d R . . C11 C 0.92609(5) 0.34982(5) 0.88507(3) 0.0221(3) Uani 1 1 d R . . H11A H 0.9608 0.4594 0.8850 0.027 Uiso 1 1 calc R . . H11B H 1.0185 0.2862 0.8616 0.027 Uiso 1 1 calc R . . Cl12 Cl 0.87169(5) 0.29356(5) 1.00963(3) 0.02617(11) Uani 1 1 d . . . 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 O1 0.0157(5) 0.0259(5) 0.0152(5) -0.0015(4) 0.0000(4) -0.0003(4) C2 0.0163(7) 0.0202(7) 0.0170(7) -0.0017(5) -0.0003(6) 0.0004(6) O3 0.0174(5) 0.0231(5) 0.0153(5) 0.0014(4) 0.0020(4) 0.0020(4) C4 0.0166(7) 0.0220(7) 0.0155(7) 0.0014(5) 0.0006(5) -0.0009(6) O5 0.0160(5) 0.0231(5) 0.0169(5) -0.0023(4) -0.0010(4) 0.0027(4) C6 0.0183(7) 0.0193(7) 0.0166(7) -0.0011(5) 0.0004(6) 0.0012(6) C7 0.0220(8) 0.0241(8) 0.0188(7) 0.0002(6) 0.0037(6) 0.0039(6) Cl8 0.0360(3) 0.0336(2) 0.0215(2) -0.00026(15) 0.00790(16) 0.01173(17) C9 0.0187(8) 0.0289(8) 0.0193(7) 0.0027(6) 0.0018(6) 0.0026(6) Cl10 0.0195(2) 0.0535(3) 0.0277(2) 0.00352(18) -0.00244(16) 0.00857(18) C11 0.0184(8) 0.0293(8) 0.0186(7) -0.0010(6) 0.0000(6) 0.0001(6) Cl12 0.0259(2) 0.0347(2) 0.01788(19) -0.00082(14) -0.00361(15) -0.00023(16) _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 C6 1.4198(17) . ? O1 C2 1.4204(17) . ? C2 O3 1.4161(17) . ? C2 C7 1.506(2) . ? C2 H2 1.0000 . ? O3 C4 1.4217(17) . ? C4 O5 1.4193(17) . ? C4 C9 1.5035(15) . ? C4 H4 1.0000 . ? O5 C6 1.4160(17) . ? C6 C11 1.5069(15) . ? C6 H6 1.0000 . ? C7 Cl8 1.7842(15) . ? C7 H7A 0.9900 . ? C7 H7B 0.9900 . ? C9 Cl10 1.7828 . ? C9 H9A 0.9900 . ? C9 H9B 0.9900 . ? C11 Cl12 1.7842 . ? C11 H11A 0.9900 . ? C11 H11B 0.9900 . ? 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 O1 C2 109.53(11) . . ? O3 C2 O1 109.80(11) . . ? O3 C2 C7 106.78(11) . . ? O1 C2 C7 108.97(12) . . ? O3 C2 H2 110.4 . . ? O1 C2 H2 110.4 . . ? C7 C2 H2 110.4 . . ? C2 O3 C4 109.35(10) . . ? O5 C4 O3 109.67(11) . . ? O5 C4 C9 106.49(10) . . ? O3 C4 C9 109.60(10) . . ? O5 C4 H4 110.3 . . ? O3 C4 H4 110.3 . . ? C9 C4 H4 110.3 . . ? C6 O5 C4 109.39(10) . . ? O5 C6 O1 109.80(11) . . ? O5 C6 C11 109.11(10) . . ? O1 C6 C11 106.31(10) . . ? O5 C6 H6 110.5 . . ? O1 C6 H6 110.5 . . ? C11 C6 H6 110.5 . . ? C2 C7 Cl8 110.17(10) . . ? C2 C7 H7A 109.6 . . ? Cl8 C7 H7A 109.6 . . ? C2 C7 H7B 109.6 . . ? Cl8 C7 H7B 109.6 . . ? H7A C7 H7B 108.1 . . ? C4 C9 Cl10 109.78(6) . . ? C4 C9 H9A 109.7 . . ? Cl10 C9 H9A 109.7 . . ? C4 C9 H9B 109.7 . . ? Cl10 C9 H9B 109.7 . . ? H9A C9 H9B 108.2 . . ? C6 C11 Cl12 110.24(6) . . ? C6 C11 H11A 109.6 . . ? Cl12 C11 H11A 109.6 . . ? C6 C11 H11B 109.6 . . ? Cl12 C11 H11B 109.6 . . ? H11A C11 H11B 108.1 . . ? 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 C6 O1 C2 O3 59.46(14) . . . . ? C6 O1 C2 C7 176.09(11) . . . . ? O1 C2 O3 C4 -59.65(14) . . . . ? C7 C2 O3 C4 -177.65(11) . . . . ? C2 O3 C4 O5 59.94(14) . . . . ? C2 O3 C4 C9 176.51(10) . . . . ? O3 C4 O5 C6 -59.98(14) . . . . ? C9 C4 O5 C6 -178.49(10) . . . . ? C4 O5 C6 O1 59.75(14) . . . . ? C4 O5 C6 C11 175.89(10) . . . . ? C2 O1 C6 O5 -59.47(14) . . . . ? C2 O1 C6 C11 -177.36(9) . . . . ? O3 C2 C7 Cl8 -173.49(9) . . . . ? O1 C2 C7 Cl8 67.97(13) . . . . ? O5 C4 C9 Cl10 -176.29(7) . . . . ? O3 C4 C9 Cl10 65.15(10) . . . . ? O5 C6 C11 Cl12 65.44(11) . . . . ? O1 C6 C11 Cl12 -176.21(7) . . . . ? _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 26.51 _diffrn_measured_fraction_theta_full 0.996 _refine_diff_density_max 0.264 _refine_diff_density_min -0.356 _refine_diff_density_rms 0.059