# Electronic Supplementary Material (ESI) for Chemical Science # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_26 _database_code_depnum_ccdc_archive 'CCDC 895406' _audit_creation_date 2011-04-04 _audit_creation_method ; Olex2 1.1-beta (compiled 2011.02.15 svn.r1672, GUI svn.r3494) ; _chemical_name_common ? _chemical_name_systematic ; 2-phenyl-3-(\a-hydroxybenzyl)-6,7-dihydro-5H-pyrrolo[2,1-c][1,2,4]triazol- 2-ium chloride deuterohydrate ; _chemical_formula_moiety 'Cl 1-,C18 H18 N3 O 1+,D2 O' _chemical_formula_sum 'C18 H18 Cl D2 N3 O2' _chemical_formula_weight 347.83 _chemical_melting_point ? 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' D D 0.0000 0.0000 '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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system orthorhombic _space_group_IT_number 61 _space_group_name_H-M_alt 'P b c a' _space_group_name_Hall '-P 2ac 2ab' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x+1/2, -y, z+1/2' 3 '-x, y+1/2, -z+1/2' 4 'x+1/2, -y+1/2, -z' 5 '-x, -y, -z' 6 'x-1/2, y, -z-1/2' 7 'x, -y-1/2, z-1/2' 8 '-x-1/2, y-1/2, z' _cell_length_a 18.9604(10) _cell_length_b 9.3522(6) _cell_length_c 19.2687(12) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3416.8(4) _cell_formula_units_Z 8 _cell_measurement_reflns_used 9138 _cell_measurement_temperature 120 _cell_measurement_theta_max 24.98 _cell_measurement_theta_min 2.37 _exptl_absorpt_coefficient_mu 0.239 _exptl_absorpt_correction_T_max ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_type none _exptl_absorpt_process_details ? _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.352 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description blade _exptl_crystal_F_000 1456 _exptl_crystal_size_max 0.53 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.05 _exptl_special_details ; The data collection nominally covered a full sphere of reciprocal space by a combination of 4 sets of \w scans each set at different \f and/or 2\q angles and each scan (30 s exposure) covering -0.3\% in \w. The crystal to detector distance was 4.85 cm. ; _diffrn_reflns_av_R_equivalents 0.0378 _diffrn_reflns_av_unetI/netI 0.0176 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_number 30562 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 25.00 _diffrn_reflns_theta_min 2.11 _diffrn_ambient_temperature 120 _diffrn_detector_area_resol_mean 5.6 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device_type 'Bruker SMART 6000 CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_source_current 35.0 _diffrn_source_power 1.75 _diffrn_source_target MO _diffrn_source_voltage 50.0 _diffrn_standards_number 0 _reflns_number_gt 2538 _reflns_number_total 3000 _reflns_threshold_expression I>2\s(I) _computing_cell_refinement 'SAINT v7.46A (Bruker, 2008)' _computing_data_collection 'SMART v5.625 (Bruker, 2001)' _computing_data_reduction 'SAINT v7.46A (Bruker, 2008)' _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement 'A short history of SHELX (Sheldrick, 2008)/Bruker' _computing_structure_solution 'A short history of SHELX (Sheldrick, 2008)/Bruker' _refine_diff_density_max 0.244 _refine_diff_density_min -0.184 _refine_diff_density_rms 0.040 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 229 _refine_ls_number_reflns 3000 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0391 _refine_ls_R_factor_gt 0.0303 _refine_ls_restrained_S_all 1.032 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0355P)^2^+1.9746P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0731 _refine_ls_wR_factor_ref 0.0798 _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. The methyl group was refined as a rigid body rotating around the C---C bond. Water deuterium and hydroxyl H atoms: refall, other H atoms: riding model. ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 Cl Cl 0.13025(2) 0.41857(4) 0.50301(2) 0.02792(12) Uani 1 1 d . . . O1 O 0.23770(6) 0.58769(12) 0.41896(6) 0.0234(3) Uani 1 1 d . . . H1 H 0.2071(11) 0.539(2) 0.4426(11) 0.040(6) Uiso 1 1 d . . . O2 O 0.02748(8) 0.66915(18) 0.45418(10) 0.0577(5) Uani 1 1 d . . . D1 D -0.0141(15) 0.652(3) 0.4638(13) 0.069(8) Uiso 1 1 d . . . D2 D 0.0504(14) 0.587(3) 0.4635(13) 0.069(8) Uiso 1 1 d . . . N1 N 0.15988(6) 0.83763(13) 0.45303(6) 0.0176(3) Uani 1 1 d . . . N2 N 0.08183(7) 0.96272(13) 0.39321(6) 0.0207(3) Uani 1 1 d . . . N3 N 0.11123(6) 0.85351(13) 0.35436(6) 0.0188(3) Uani 1 1 d . . . C1 C 0.15837(7) 0.77782(16) 0.39025(7) 0.0175(3) Uani 1 1 d . . . C2 C 0.19200(8) 0.81176(17) 0.52166(8) 0.0218(3) Uani 1 1 d . . . H2A H 0.2438 0.7969 0.5182 0.026 Uiso 1 1 d R . . H2B H 0.1701 0.7289 0.5447 0.026 Uiso 1 1 d R . . C3 C 0.17349(9) 0.95211(17) 0.55974(8) 0.0252(4) Uani 1 1 d . . . H3A H 0.2145 1.0175 0.5582 0.030 Uiso 1 1 d R . . H3B H 0.1618 0.9326 0.6089 0.030 Uiso 1 1 d R . . C4 C 0.10886(9) 1.01830(17) 0.52215(8) 0.0254(4) Uani 1 1 d . . . H4A H 0.0640 0.9955 0.5462 0.030 Uiso 1 1 d R . . H4B H 0.1139 1.1226 0.5185 0.030 Uiso 1 1 d R . . C5 C 0.11290(8) 0.94820(16) 0.45295(8) 0.0197(3) Uani 1 1 d . . . C6 C 0.20214(8) 0.65373(16) 0.36334(8) 0.0197(3) Uani 1 1 d . . . H6 H 0.1700 0.5837 0.3404 0.024 Uiso 1 1 d R . . C7 C 0.25559(8) 0.70631(15) 0.31024(8) 0.0193(3) Uani 1 1 d . . . C8 C 0.31696(8) 0.77424(16) 0.33217(8) 0.0220(3) Uani 1 1 d . . . H8 H 0.3250 0.7861 0.3804 0.026 Uiso 1 1 d R . . C9 C 0.36535(8) 0.82285(17) 0.28379(9) 0.0258(4) Uani 1 1 d . . . H9 H 0.4073 0.8689 0.2992 0.031 Uiso 1 1 d R . . C10 C 0.35316(9) 0.80415(18) 0.21329(9) 0.0295(4) Uani 1 1 d . . . H10 H 0.3864 0.8381 0.1802 0.035 Uiso 1 1 d R . . C11 C 0.29245(9) 0.7359(2) 0.19155(9) 0.0312(4) Uani 1 1 d . . . H11 H 0.2850 0.7243 0.1432 0.037 Uiso 1 1 d R . . C12 C 0.24369(8) 0.68671(18) 0.23975(8) 0.0262(4) Uani 1 1 d . . . H12 H 0.2021 0.6401 0.2239 0.031 Uiso 1 1 d R . . C14 C 0.08847(8) 0.82903(17) 0.28420(7) 0.0198(3) Uani 1 1 d . . . C15 C 0.05175(8) 0.70514(17) 0.26881(8) 0.0237(4) Uani 1 1 d . . . H15 H 0.0405 0.6372 0.3035 0.028 Uiso 1 1 d R . . C16 C 0.03203(8) 0.68144(19) 0.20047(9) 0.0286(4) Uani 1 1 d . . . H16 H 0.0085 0.5964 0.1875 0.034 Uiso 1 1 d R . . C17 C 0.04766(8) 0.7819(2) 0.14978(9) 0.0305(4) Uani 1 1 d . . . H17 H 0.0341 0.7665 0.1030 0.037 Uiso 1 1 d R . . C18 C 0.08342(9) 0.90630(19) 0.16668(8) 0.0305(4) Uani 1 1 d . . . H18 H 0.0932 0.9762 0.1325 0.037 Uiso 1 1 d R . . C19 C 0.10441(9) 0.93040(17) 0.23454(8) 0.0248(4) Uani 1 1 d . . . H19 H 0.1287 1.0145 0.2475 0.030 Uiso 1 1 d R . . 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 Cl 0.0268(2) 0.0266(2) 0.0304(2) -0.00128(17) 0.00806(17) 0.00051(16) O1 0.0230(6) 0.0227(6) 0.0244(6) 0.0068(5) -0.0010(5) 0.0030(5) O2 0.0268(8) 0.0516(10) 0.0947(13) 0.0413(9) 0.0025(8) -0.0058(7) N1 0.0179(6) 0.0168(6) 0.0181(6) 0.0008(5) 0.0000(5) -0.0009(5) N2 0.0235(7) 0.0176(6) 0.0212(7) -0.0001(5) 0.0005(5) 0.0025(5) N3 0.0206(6) 0.0174(6) 0.0184(6) 0.0005(5) -0.0006(5) 0.0011(5) C1 0.0161(7) 0.0169(7) 0.0194(7) 0.0023(6) 0.0005(6) -0.0022(6) C2 0.0243(8) 0.0226(8) 0.0184(7) 0.0020(6) -0.0039(6) -0.0010(6) C3 0.0292(8) 0.0267(9) 0.0196(8) -0.0026(7) -0.0012(7) -0.0017(7) C4 0.0319(9) 0.0213(8) 0.0229(8) -0.0017(7) 0.0022(7) 0.0020(7) C5 0.0215(7) 0.0164(7) 0.0213(8) 0.0023(6) 0.0014(6) -0.0005(6) C6 0.0214(7) 0.0179(8) 0.0198(7) 0.0003(6) -0.0020(6) 0.0016(6) C7 0.0189(7) 0.0159(7) 0.0230(7) -0.0006(6) 0.0000(6) 0.0050(6) C8 0.0234(8) 0.0186(8) 0.0240(8) -0.0025(7) -0.0012(6) 0.0034(6) C9 0.0217(8) 0.0178(8) 0.0380(10) 0.0004(7) 0.0016(7) 0.0019(6) C10 0.0271(9) 0.0269(9) 0.0346(9) 0.0103(7) 0.0088(7) 0.0062(7) C11 0.0314(9) 0.0418(10) 0.0205(8) 0.0048(8) -0.0007(7) 0.0082(8) C12 0.0218(8) 0.0330(9) 0.0237(8) -0.0015(7) -0.0034(7) 0.0030(7) C14 0.0177(7) 0.0232(8) 0.0185(7) -0.0006(6) -0.0017(6) 0.0044(6) C15 0.0194(7) 0.0256(9) 0.0261(8) 0.0018(7) -0.0016(6) -0.0005(6) C16 0.0213(8) 0.0330(9) 0.0315(9) -0.0083(8) -0.0045(7) -0.0003(7) C17 0.0258(8) 0.0452(11) 0.0205(8) -0.0066(8) -0.0032(7) 0.0094(8) C18 0.0351(9) 0.0354(10) 0.0210(8) 0.0050(7) 0.0030(7) 0.0076(8) C19 0.0282(8) 0.0226(8) 0.0236(8) 0.0016(7) 0.0012(7) 0.0022(7) _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 H1 0.87(2) . ? O1 C6 1.4088(18) . ? O2 D1 0.83(3) . ? O2 D2 0.90(3) . ? N1 C1 1.3332(19) . ? N1 C2 1.4760(18) . ? N1 C5 1.3648(19) . ? N2 N3 1.3835(17) . ? N2 C5 1.300(2) . ? N3 C1 1.3334(19) . ? N3 C14 1.4374(19) . ? C1 C6 1.518(2) . ? C2 H2A 0.9937 . ? C2 H2B 0.9855 . ? C2 C3 1.544(2) . ? C3 H3A 0.9895 . ? C3 H3B 0.9889 . ? C3 C4 1.552(2) . ? C4 H4A 0.9923 . ? C4 H4B 0.9824 . ? C4 C5 1.488(2) . ? C6 H6 0.9977 . ? C6 C7 1.522(2) . ? C7 C8 1.391(2) . ? C7 C12 1.389(2) . ? C8 H8 0.9488 . ? C8 C9 1.385(2) . ? C9 H9 0.9513 . ? C9 C10 1.389(2) . ? C10 H10 0.9502 . ? C10 C11 1.381(2) . ? C11 H11 0.9489 . ? C11 C12 1.389(2) . ? C12 H12 0.9508 . ? C14 C15 1.384(2) . ? C14 C19 1.381(2) . ? C15 H15 0.9462 . ? C15 C16 1.387(2) . ? C16 H16 0.9454 . ? C16 C17 1.387(3) . ? C17 H17 0.9489 . ? C17 C18 1.385(3) . ? C18 H18 0.9462 . ? C18 C19 1.385(2) . ? C19 H19 0.9456 . ? 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 H1 108.0(13) . . ? D1 O2 D2 104(2) . . ? C1 N1 C2 138.86(13) . . ? C1 N1 C5 107.63(12) . . ? C5 N1 C2 113.24(12) . . ? C5 N2 N3 102.67(12) . . ? N2 N3 C14 120.36(12) . . ? C1 N3 N2 112.42(12) . . ? C1 N3 C14 127.18(13) . . ? N1 C1 N3 105.20(13) . . ? N1 C1 C6 128.24(13) . . ? N3 C1 C6 126.53(13) . . ? N1 C2 H2A 111.7 . . ? N1 C2 H2B 111.1 . . ? N1 C2 C3 101.10(12) . . ? H2A C2 H2B 109.7 . . ? C3 C2 H2A 112.0 . . ? C3 C2 H2B 111.0 . . ? C2 C3 H3A 109.4 . . ? C2 C3 H3B 110.4 . . ? C2 C3 C4 107.26(12) . . ? H3A C3 H3B 108.5 . . ? C4 C3 H3A 111.1 . . ? C4 C3 H3B 110.1 . . ? C3 C4 H4A 111.9 . . ? C3 C4 H4B 110.7 . . ? H4A C4 H4B 109.2 . . ? C5 C4 C3 101.65(12) . . ? C5 C4 H4A 111.6 . . ? C5 C4 H4B 111.6 . . ? N1 C5 C4 111.49(13) . . ? N2 C5 N1 112.08(13) . . ? N2 C5 C4 136.40(14) . . ? O1 C6 C1 109.69(12) . . ? O1 C6 H6 109.9 . . ? O1 C6 C7 109.54(12) . . ? C1 C6 H6 108.7 . . ? C1 C6 C7 110.28(12) . . ? C7 C6 H6 108.7 . . ? C8 C7 C6 120.02(13) . . ? C12 C7 C6 120.44(14) . . ? C12 C7 C8 119.53(14) . . ? C7 C8 H8 119.0 . . ? C9 C8 C7 119.97(15) . . ? C9 C8 H8 121.0 . . ? C8 C9 H9 119.5 . . ? C8 C9 C10 120.45(15) . . ? C10 C9 H9 120.1 . . ? C9 C10 H10 120.2 . . ? C11 C10 C9 119.57(15) . . ? C11 C10 H10 120.2 . . ? C10 C11 H11 118.4 . . ? C10 C11 C12 120.33(16) . . ? C12 C11 H11 121.3 . . ? C7 C12 H12 120.6 . . ? C11 C12 C7 120.14(15) . . ? C11 C12 H12 119.3 . . ? C15 C14 N3 119.07(13) . . ? C19 C14 N3 118.48(14) . . ? C19 C14 C15 122.44(14) . . ? C14 C15 H15 121.6 . . ? C14 C15 C16 118.23(15) . . ? C16 C15 H15 120.1 . . ? C15 C16 H16 120.8 . . ? C15 C16 C17 120.18(16) . . ? C17 C16 H16 119.0 . . ? C16 C17 H17 120.6 . . ? C18 C17 C16 120.52(15) . . ? C18 C17 H17 118.9 . . ? C17 C18 H18 120.8 . . ? C19 C18 C17 119.94(16) . . ? C19 C18 H18 119.2 . . ? C14 C19 C18 118.67(15) . . ? C14 C19 H19 119.6 . . ? C18 C19 H19 121.7 . . ? 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 O1 H1 Cl 0.87(2) 2.18(2) 3.0455(12) 179(2) . O2 D1 Cl 0.83(3) 2.39(3) 3.2090(16) 175(2) 5_566 O2 D2 Cl 0.90(3) 2.32(3) 3.1896(17) 164(2) . data_36 _database_code_depnum_ccdc_archive 'CCDC 895407' _audit_creation_date 2011-03-23 _audit_creation_method ; Olex2 1.1-beta (compiled 2011.02.15 svn.r1672, GUI svn.r3494) ; _chemical_name_common ? _chemical_name_systematic ;2-phenyl-3-(\a-hydroxy-paramethylbenzyl)-6,7-dihydro-5H-pyrrolo[2,1- c][1,2,4]triazol-2-ium chloride deuterohydrate ; _chemical_formula_moiety 'Cl 1-,C19 H20 N3 O 1+,D2 O' _chemical_formula_sum 'C19 H20 Cl D2 N3 O2' _chemical_formula_weight 361.85 _chemical_melting_point ? 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' Cl Cl 0.1484 0.1585 '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' _space_group_crystal_system orthorhombic _space_group_IT_number 61 _space_group_name_H-M_alt 'P b c a' _space_group_name_Hall '-P 2ac 2ab' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x+1/2, -y, z+1/2' 3 'x+1/2, -y+1/2, -z' 4 '-x, y+1/2, -z+1/2' 5 '-x, -y, -z' 6 'x-1/2, y, -z-1/2' 7 '-x-1/2, y-1/2, z' 8 'x, -y-1/2, z-1/2' _cell_length_a 19.2697(16) _cell_length_b 9.5129(8) _cell_length_c 19.6896(16) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3609.3(5) _cell_formula_units_Z 8 _cell_measurement_reflns_used 2675 _cell_measurement_temperature 120 _cell_measurement_theta_max 21.86 _cell_measurement_theta_min 2.32 _exptl_absorpt_coefficient_mu 0.229 _exptl_absorpt_correction_T_max ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_type none _exptl_absorpt_process_details ? _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.332 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description needle _exptl_crystal_F_000 1520 _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.03 _exptl_special_details ; The data collection nominally covered a full sphere of reciprocal space by a combination of 3 sets of \w scans each set at different \f and/or 2\q angles and each scan (30 s exposure) covering -0.3\% in \w. The crystal to detector distance was 4.85 cm. The diffraction is very weak: mean I/\s(I)=2.85, which explains the high R~int~. ; _diffrn_reflns_av_R_equivalents 0.1899 _diffrn_reflns_av_unetI/netI 0.1240 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 23 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_number 33554 _diffrn_reflns_theta_full 25.02 _diffrn_reflns_theta_max 25.02 _diffrn_reflns_theta_min 2.07 _diffrn_ambient_temperature 120 _diffrn_detector_area_resol_mean 5.6 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device_type 'Bruker SMART 6000 CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 -0.027797 _diffrn_orient_matrix_UB_12 0.013986 _diffrn_orient_matrix_UB_13 0.043283 _diffrn_orient_matrix_UB_21 0.048747 _diffrn_orient_matrix_UB_22 0.025085 _diffrn_orient_matrix_UB_23 0.012652 _diffrn_orient_matrix_UB_31 -0.023013 _diffrn_orient_matrix_UB_32 0.036250 _diffrn_orient_matrix_UB_33 -0.025460 _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_source_current 35.0 _diffrn_source_power 1.75 _diffrn_source_target MO _diffrn_source_voltage 50.0 _diffrn_standards_number 0 _reflns_number_gt 1513 _reflns_number_total 3182 _reflns_threshold_expression I>2\s(I) _computing_cell_refinement 'SAINT v7.46A (Bruker, 2008)' _computing_data_collection 'SMART v5.625 (Bruker, 2001)' _computing_data_reduction 'SAINT v7.46A (Bruker, 2008)' _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'A short history of SHELX (Sheldrick, 2008)/Bruker' _refine_diff_density_max 0.256 _refine_diff_density_min -0.249 _refine_diff_density_rms 0.065 _refine_ls_extinction_coef 0.0025(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method SHELXL _refine_ls_goodness_of_fit_ref 0.905 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 240 _refine_ls_number_reflns 3182 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1355 _refine_ls_R_factor_gt 0.0475 _refine_ls_restrained_S_all 0.905 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0479P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0938 _refine_ls_wR_factor_ref 0.1198 _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. The methyl group was refined as a rigid body rotating around the C---C bond. Water deuterium and hydroxyl H atoms: refall, other H atoms: riding model. ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 Cl Cl 0.12595(5) 0.39192(11) 0.49093(5) 0.0360(3) Uani 1 1 d . . . O1 O 0.23223(13) 0.5485(3) 0.40609(13) 0.0297(7) Uani 1 1 d . . . H1 H 0.2008(19) 0.499(4) 0.4322(18) 0.043(13) Uiso 1 1 d . . . O2 O 0.02974(18) 0.6509(4) 0.4492(2) 0.0687(13) Uani 1 1 d . . . D1 D -0.006(3) 0.645(5) 0.469(2) 0.071(19) Uiso 1 1 d . . . D2 D 0.054(3) 0.564(7) 0.458(3) 0.16(3) Uiso 1 1 d . . . N1 N 0.16169(13) 0.8017(3) 0.43724(15) 0.0217(7) Uani 1 1 d . . . N2 N 0.08776(14) 0.9303(3) 0.37832(16) 0.0262(8) Uani 1 1 d . . . N3 N 0.11341(14) 0.8182(3) 0.34079(14) 0.0228(7) Uani 1 1 d . . . C1 C 0.15797(17) 0.7411(4) 0.37650(19) 0.0221(9) Uani 1 1 d . . . C2 C 0.19348(17) 0.7772(4) 0.50423(18) 0.0268(9) Uani 1 1 d . . . H2C H 0.2441 0.7612 0.5004 0.032 Uiso 1 1 calc R . . H2D H 0.1718 0.6964 0.5278 0.032 Uiso 1 1 calc R . . C3 C 0.17741(18) 0.9165(4) 0.54060(19) 0.0306(10) Uani 1 1 d . . . H3A H 0.2185 0.9789 0.5394 0.037 Uiso 1 1 calc R . . H3B H 0.1652 0.8985 0.5887 0.037 Uiso 1 1 calc R . . C4 C 0.11582(18) 0.9863(4) 0.50333(17) 0.0284(9) Uani 1 1 d . . . H4A H 0.0714 0.9683 0.5270 0.034 Uiso 1 1 calc R . . H4B H 0.1227 1.0889 0.4985 0.034 Uiso 1 1 calc R . . C5 C 0.11824(17) 0.9144(4) 0.43652(18) 0.0224(9) Uani 1 1 d . . . C6 C 0.19913(17) 0.6158(4) 0.35151(18) 0.0241(9) Uani 1 1 d . . . H6 H 0.1668 0.5479 0.3291 0.029 Uiso 1 1 calc R . . C7 C 0.25249(18) 0.6647(4) 0.30014(18) 0.0225(9) Uani 1 1 d . . . C8 C 0.31225(17) 0.7333(4) 0.32234(18) 0.0244(9) Uani 1 1 d . . . H8 H 0.3204 0.7453 0.3696 0.029 Uiso 1 1 calc R . . C9 C 0.35973(18) 0.7838(4) 0.27570(19) 0.0259(9) Uani 1 1 d . . . H9 H 0.4003 0.8302 0.2915 0.031 Uiso 1 1 calc R . . C10 C 0.34938(18) 0.7681(4) 0.20613(19) 0.0256(9) Uani 1 1 d . . . C11 C 0.28980(17) 0.6981(4) 0.18493(19) 0.0283(10) Uani 1 1 d . . . H11 H 0.2818 0.6847 0.1378 0.034 Uiso 1 1 calc R . . C12 C 0.24191(18) 0.6477(4) 0.23154(19) 0.0287(10) Uani 1 1 d . . . H12 H 0.2014 0.6009 0.2159 0.034 Uiso 1 1 calc R . . C13 C 0.40164(18) 0.8204(4) 0.15517(18) 0.0336(10) Uani 1 1 d . . . H13A H 0.4028 0.9233 0.1561 0.050 Uiso 1 1 calc R . . H13B H 0.3884 0.7884 0.1097 0.050 Uiso 1 1 calc R . . H13C H 0.4476 0.7834 0.1666 0.050 Uiso 1 1 calc R . . C14 C 0.09056(17) 0.8012(4) 0.27180(18) 0.0228(9) Uani 1 1 d . . . C15 C 0.05196(18) 0.6851(4) 0.2543(2) 0.0298(10) Uani 1 1 d . . . H15 H 0.0417 0.6138 0.2866 0.036 Uiso 1 1 calc R . . C16 C 0.02851(18) 0.6759(4) 0.1875(2) 0.0375(11) Uani 1 1 d . . . H16 H 0.0017 0.5969 0.1740 0.045 Uiso 1 1 calc R . . C17 C 0.04352(19) 0.7793(4) 0.1406(2) 0.0361(11) Uani 1 1 d . . . H17 H 0.0270 0.7713 0.0953 0.043 Uiso 1 1 calc R . . C18 C 0.08257(19) 0.8945(5) 0.1597(2) 0.0361(10) Uani 1 1 d . . . H18 H 0.0931 0.9657 0.1275 0.043 Uiso 1 1 calc R . . C19 C 0.10640(17) 0.9060(4) 0.22599(19) 0.0298(10) Uani 1 1 d . . . H19 H 0.1332 0.9849 0.2396 0.036 Uiso 1 1 calc R . . 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 Cl 0.0271(5) 0.0394(6) 0.0414(6) 0.0053(6) 0.0104(5) 0.0022(5) O1 0.0224(16) 0.0344(17) 0.0324(17) 0.0077(14) 0.0004(13) 0.0035(12) O2 0.0201(19) 0.071(3) 0.115(3) 0.053(2) 0.010(2) 0.0017(17) N1 0.0137(16) 0.0275(19) 0.0240(19) 0.0028(16) 0.0002(13) 0.0007(14) N2 0.0222(17) 0.0262(19) 0.0300(19) -0.0023(16) -0.0018(15) -0.0005(14) N3 0.0172(16) 0.0263(17) 0.0251(19) 0.0038(17) 0.0000(14) 0.0019(14) C1 0.0139(19) 0.024(2) 0.029(2) 0.0042(19) 0.0007(17) -0.0003(16) C2 0.0169(19) 0.034(2) 0.030(2) 0.006(2) -0.0048(17) -0.0005(16) C3 0.022(2) 0.039(3) 0.030(2) 0.001(2) -0.0019(17) -0.0022(18) C4 0.028(2) 0.033(2) 0.025(2) -0.002(2) -0.0007(19) 0.0002(17) C5 0.0132(19) 0.025(2) 0.029(2) -0.0009(19) 0.0026(17) -0.0016(16) C6 0.017(2) 0.026(2) 0.030(2) 0.004(2) -0.0029(16) 0.0041(17) C7 0.0175(19) 0.022(2) 0.028(2) -0.0028(19) 0.0018(17) 0.0036(16) C8 0.021(2) 0.029(2) 0.023(2) -0.0012(19) 0.0002(16) 0.0043(17) C9 0.018(2) 0.022(2) 0.038(3) -0.0011(19) -0.0003(17) 0.0021(16) C10 0.017(2) 0.030(2) 0.031(2) 0.0030(19) 0.0013(17) 0.0052(17) C11 0.021(2) 0.040(2) 0.024(2) 0.000(2) -0.0014(17) 0.0047(18) C12 0.018(2) 0.036(2) 0.032(2) -0.001(2) -0.0025(18) 0.0008(17) C13 0.027(2) 0.039(2) 0.035(3) 0.007(2) 0.0050(18) 0.0015(19) C14 0.017(2) 0.028(2) 0.024(2) -0.003(2) -0.0036(16) 0.0028(17) C15 0.017(2) 0.029(2) 0.043(3) -0.003(2) -0.0004(18) -0.0013(18) C16 0.018(2) 0.042(3) 0.053(3) -0.016(3) -0.003(2) 0.0009(19) C17 0.029(2) 0.048(3) 0.032(3) -0.006(2) -0.0052(19) 0.006(2) C18 0.035(2) 0.042(3) 0.031(2) 0.001(2) -0.0003(19) 0.006(2) C19 0.025(2) 0.031(2) 0.034(2) -0.003(2) -0.0034(17) -0.0028(18) _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 1.404(4) . ? N1 C1 1.330(4) . ? N1 C2 1.473(4) . ? N1 C5 1.361(4) . ? N2 N3 1.389(4) . ? N2 C5 1.297(4) . ? N3 C1 1.330(4) . ? N3 C14 1.437(4) . ? C1 C6 1.514(5) . ? C2 C3 1.537(5) . ? C3 C4 1.545(5) . ? C4 C5 1.483(5) . ? C6 C7 1.515(5) . ? C7 C8 1.394(5) . ? C7 C12 1.375(5) . ? C8 C9 1.383(5) . ? C9 C10 1.392(5) . ? C10 C11 1.391(5) . ? C10 C13 1.506(5) . ? C11 C12 1.387(5) . ? C14 C15 1.376(5) . ? C14 C19 1.379(5) . ? C15 C16 1.394(5) . ? C16 C17 1.379(5) . ? C17 C18 1.381(5) . ? C18 C19 1.387(5) . ? 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 C1 N1 C2 139.4(3) . . ? C1 N1 C5 107.4(3) . . ? C5 N1 C2 112.9(3) . . ? C5 N2 N3 102.7(3) . . ? N2 N3 C14 118.7(3) . . ? C1 N3 N2 111.8(3) . . ? C1 N3 C14 129.5(3) . . ? N1 C1 N3 105.7(3) . . ? N1 C1 C6 127.3(3) . . ? N3 C1 C6 126.9(3) . . ? N1 C2 C3 101.4(3) . . ? C2 C3 C4 107.7(3) . . ? C5 C4 C3 101.5(3) . . ? N1 C5 C4 111.9(3) . . ? N2 C5 N1 112.3(3) . . ? N2 C5 C4 135.7(3) . . ? O1 C6 C1 110.4(3) . . ? O1 C6 C7 110.0(3) . . ? C1 C6 C7 109.3(3) . . ? C8 C7 C6 119.7(3) . . ? C12 C7 C6 121.3(3) . . ? C12 C7 C8 119.0(3) . . ? C9 C8 C7 120.1(3) . . ? C8 C9 C10 121.4(3) . . ? C9 C10 C13 121.6(3) . . ? C11 C10 C9 117.7(3) . . ? C11 C10 C13 120.7(3) . . ? C12 C11 C10 121.1(3) . . ? C7 C12 C11 120.7(3) . . ? C15 C14 N3 119.5(3) . . ? C15 C14 C19 122.5(3) . . ? C19 C14 N3 118.0(3) . . ? C14 C15 C16 117.5(4) . . ? C17 C16 C15 121.2(4) . . ? C16 C17 C18 119.9(4) . . ? C17 C18 C19 119.9(4) . . ? C14 C19 C18 119.0(4) . . ? 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 O1 H1 Cl 0.93(4) 2.11(4) 3.033(3) 177(3) . O2 D1 Cl 0.79(5) 2.47(5) 3.249(4) 169(5) 5_566 O2 D2 Cl 0.97(7) 2.24(7) 3.191(4) 168(5) . data_37 _database_code_depnum_ccdc_archive 'CCDC 895408' _audit_creation_date 2011-03-29 _audit_creation_method ; Olex2 1.1-beta (compiled 2011.02.15 svn.r1672, GUI svn.r3494) ; _chemical_name_common ? _chemical_name_systematic ;2-phenyl-3-(\a-hydroxy-parafluorobenzyl)-6,7-dihydro-5H-pyrrolo[2,1- c][1,2,4]triazol-2-ium chloride deuterohydrate ; _chemical_formula_moiety 'Cl 1-,C18 H17 F N3 O 1+,D2 O' _chemical_formula_sum 'C18 H17 Cl D2 F N3 O2' _chemical_formula_weight 365.82 _chemical_melting_point ? 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' D D 0.0000 0.0000 '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' F F 0.0171 0.0103 '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' _space_group_crystal_system orthorhombic _space_group_IT_number 61 _space_group_name_H-M_alt 'P b c a' _space_group_name_Hall '-P 2ac 2ab' loop_ _space_group_symop_id _space_group_symop_operation_xyz 1 'x, y, z' 2 '-x+1/2, -y, z+1/2' 3 '-x, y+1/2, -z+1/2' 4 'x+1/2, -y+1/2, -z' 5 '-x, -y, -z' 6 'x-1/2, y, -z-1/2' 7 'x, -y-1/2, z-1/2' 8 '-x-1/2, y-1/2, z' _cell_length_a 18.8845(8) _cell_length_b 9.4266(4) _cell_length_c 19.2915(9) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 3434.2(3) _cell_formula_units_Z 8 _cell_measurement_reflns_used 9971 _cell_measurement_temperature 120(2) _cell_measurement_theta_max 27.03 _cell_measurement_theta_min 2.16 _exptl_absorpt_coefficient_mu 0.250 _exptl_absorpt_correction_T_max ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_type none _exptl_absorpt_process_details ? _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.415 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description needle _exptl_crystal_F_000 1520 _exptl_crystal_size_max 0.6 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_min 0.05 _exptl_special_details ;The data collection nominally covered full sphere of reciprocal space, by a combination of 4 runs of narrow-frame \w-scans (scan width 0.3\% \w, 30 s exposure), every run at a different \f and/or 2\qangle. Crystal to detector distance 4.84 cm. ; _diffrn_reflns_av_R_equivalents 0.0454 _diffrn_reflns_av_unetI/netI 0.0217 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_number 33716 _diffrn_reflns_theta_full 25.00 _diffrn_reflns_theta_max 25.00 _diffrn_reflns_theta_min 2.11 _diffrn_ambient_temperature 120(2) _diffrn_detector_area_resol_mean 5.6 _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_device_type 'Bruker SMART 6000 CCD area detector' _diffrn_measurement_method '\w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_source 'fine-focus sealed tube' _diffrn_source_current 35.0 _diffrn_source_power 1.75 _diffrn_source_voltage 50.0 _diffrn_standards_number 0 _reflns_number_gt 2497 _reflns_number_total 3029 _reflns_threshold_expression I>2\s(I) _computing_cell_refinement 'SAINT v7.46A (Bruker, 2008)' _computing_data_collection 'SMART v5.625 (Bruker, 2001)' _computing_data_reduction 'SAINT v7.46A (Bruker, 2008)' _computing_molecular_graphics ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_publication_material ; O. V. Dolomanov, L. J. Bourhis, R. J. Gildea, J. A. K. Howard and H. Puschmann, OLEX2: a complete structure solution, refinement and analysis program. J. Appl. Cryst. (2009). 42, 339-341. ; _computing_structure_refinement 'A short history of SHELX (Sheldrick, 2008)/Bruker' _computing_structure_solution 'A short history of SHELX (Sheldrick, 2008)/Bruker' _refine_diff_density_max 0.255 _refine_diff_density_min -0.210 _refine_diff_density_rms 0.045 _refine_ls_extinction_coef ? _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.068 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 238 _refine_ls_number_reflns 3029 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0439 _refine_ls_R_factor_gt 0.0319 _refine_ls_restrained_S_all 1.068 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0385P)^2^+1.9833P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0773 _refine_ls_wR_factor_ref 0.0863 _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. The methyl group was refined as a rigid body rotating around the C---C bond. Water deuterium and hydroxyl H atoms: refall, other H atoms: riding model. ; _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap 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 Cl Cl 0.13055(2) 0.41479(5) 0.50344(2) 0.02807(14) Uani 1 1 d . . . O1 O 0.23611(6) 0.58605(13) 0.41875(6) 0.0233(3) Uani 1 1 d . . . H1 H 0.2040(12) 0.539(2) 0.4413(12) 0.042(6) Uiso 1 1 d . . . O2 O 0.02906(9) 0.6627(2) 0.45156(12) 0.0653(6) Uani 1 1 d . . . D1 D -0.0128(17) 0.651(3) 0.4624(14) 0.068(9) Uiso 1 1 d . . . D2 D 0.0509(17) 0.584(3) 0.4592(15) 0.073(10) Uiso 1 1 d . . . N1 N 0.15920(7) 0.83551(15) 0.45303(7) 0.0177(3) Uani 1 1 d . . . N2 N 0.08157(7) 0.96178(15) 0.39317(7) 0.0206(3) Uani 1 1 d . . . N3 N 0.11045(7) 0.85268(14) 0.35448(7) 0.0182(3) Uani 1 1 d . . . C1 C 0.15722(8) 0.77614(18) 0.39027(8) 0.0177(4) Uani 1 1 d . . . C2 C 0.19119(9) 0.80868(19) 0.52148(8) 0.0216(4) Uani 1 1 d . . . H2A H 0.2430 0.7939 0.5180 0.026 Uiso 1 1 d R . . H2B H 0.1693 0.7258 0.5446 0.026 Uiso 1 1 d R . . C3 C 0.17333(10) 0.94822(19) 0.55959(9) 0.0244(4) Uani 1 1 d . . . H3A H 0.2143 1.0135 0.5581 0.029 Uiso 1 1 d R . . H3B H 0.1617 0.9287 0.6087 0.029 Uiso 1 1 d R . . C4 C 0.10897(10) 1.01554(19) 0.52234(9) 0.0246(4) Uani 1 1 d . . . H4A H 0.0641 0.9928 0.5464 0.029 Uiso 1 1 d R . . H4B H 0.1140 1.1198 0.5187 0.029 Uiso 1 1 d R . . C5 C 0.11269(9) 0.94633(17) 0.45309(9) 0.0192(4) Uani 1 1 d . . . C6 C 0.20088(9) 0.65255(18) 0.36334(8) 0.0194(4) Uani 1 1 d . . . H6 H 0.1688 0.5825 0.3404 0.023 Uiso 1 1 d R . . C7 C 0.25493(9) 0.70520(17) 0.31100(8) 0.0188(4) Uani 1 1 d . . . C8 C 0.31628(9) 0.77212(18) 0.33399(9) 0.0209(4) Uani 1 1 d . . . H8 H 0.3243 0.7840 0.3822 0.025 Uiso 1 1 d R . . C9 C 0.36575(9) 0.82169(18) 0.28680(9) 0.0234(4) Uani 1 1 d . . . H9 H 0.4076 0.8678 0.3022 0.028 Uiso 1 1 d R . . C10 C 0.35300(9) 0.80295(19) 0.21723(9) 0.0248(4) Uani 1 1 d . . . C11 C 0.29313(10) 0.7364(2) 0.19250(9) 0.0276(4) Uani 1 1 d . . . H11 H 0.2857 0.7247 0.1441 0.033 Uiso 1 1 d R . . C12 C 0.24395(9) 0.68724(19) 0.24027(9) 0.0244(4) Uani 1 1 d . . . H12 H 0.2024 0.6407 0.2244 0.029 Uiso 1 1 d R . . F F 0.40194(6) 0.84944(12) 0.17096(6) 0.0353(3) Uani 1 1 d . . . C14 C 0.08805(8) 0.83003(18) 0.28406(8) 0.0188(4) Uani 1 1 d . . . C15 C 0.05229(9) 0.70666(19) 0.26739(9) 0.0230(4) Uani 1 1 d . . . H15 H 0.0410 0.6387 0.3020 0.028 Uiso 1 1 d R . . C16 C 0.03321(9) 0.6849(2) 0.19875(9) 0.0273(4) Uani 1 1 d . . . H16 H 0.0097 0.5998 0.1858 0.033 Uiso 1 1 d R . . C17 C 0.04832(10) 0.7866(2) 0.14897(10) 0.0292(4) Uani 1 1 d . . . H17 H 0.0348 0.7712 0.1021 0.035 Uiso 1 1 d R . . C18 C 0.08309(10) 0.9107(2) 0.16717(9) 0.0294(4) Uani 1 1 d . . . H18 H 0.0928 0.9806 0.1330 0.035 Uiso 1 1 d R . . C19 C 0.10363(9) 0.93247(19) 0.23542(9) 0.0244(4) Uani 1 1 d . . . H19 H 0.1280 1.0166 0.2484 0.029 Uiso 1 1 d R . . 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 Cl 0.0264(2) 0.0281(3) 0.0298(2) -0.00039(18) 0.00890(19) 0.00057(18) O1 0.0211(6) 0.0245(7) 0.0244(6) 0.0066(5) -0.0002(5) 0.0028(5) O2 0.0238(8) 0.0655(13) 0.1067(16) 0.0542(12) 0.0004(9) -0.0066(9) N1 0.0167(7) 0.0193(7) 0.0170(7) 0.0012(6) 0.0000(6) -0.0013(6) N2 0.0224(7) 0.0199(8) 0.0196(7) -0.0006(6) 0.0005(6) 0.0030(6) N3 0.0187(7) 0.0180(7) 0.0178(7) 0.0003(6) 0.0000(6) -0.0001(6) C1 0.0161(8) 0.0194(9) 0.0175(8) 0.0020(7) 0.0002(7) -0.0028(6) C2 0.0217(9) 0.0253(9) 0.0179(8) 0.0026(7) -0.0030(7) 0.0003(7) C3 0.0262(9) 0.0274(10) 0.0197(9) -0.0016(7) -0.0010(7) -0.0003(7) C4 0.0293(10) 0.0242(9) 0.0202(9) -0.0024(7) 0.0008(7) 0.0030(8) C5 0.0194(8) 0.0173(9) 0.0210(9) 0.0021(7) 0.0008(7) -0.0010(7) C6 0.0197(8) 0.0190(9) 0.0195(8) -0.0005(7) -0.0011(7) 0.0014(7) C7 0.0182(8) 0.0175(9) 0.0208(8) -0.0006(7) -0.0002(7) 0.0044(7) C8 0.0219(9) 0.0191(9) 0.0215(9) -0.0025(7) -0.0011(7) 0.0041(7) C9 0.0200(9) 0.0183(9) 0.0319(10) -0.0008(7) -0.0004(8) 0.0019(7) C10 0.0216(9) 0.0240(10) 0.0288(10) 0.0089(8) 0.0064(8) 0.0059(7) C11 0.0274(9) 0.0363(11) 0.0190(9) 0.0032(8) -0.0011(8) 0.0060(8) C12 0.0205(9) 0.0298(10) 0.0228(9) -0.0006(8) -0.0025(8) 0.0019(7) F 0.0292(6) 0.0424(7) 0.0344(6) 0.0141(5) 0.0112(5) 0.0009(5) C14 0.0160(8) 0.0229(9) 0.0174(8) -0.0015(7) -0.0011(7) 0.0044(7) C15 0.0169(8) 0.0258(10) 0.0263(10) 0.0006(8) -0.0005(7) 0.0004(7) C16 0.0200(9) 0.0319(11) 0.0301(10) -0.0087(8) -0.0039(8) 0.0013(8) C17 0.0248(9) 0.0422(12) 0.0207(9) -0.0059(8) -0.0024(8) 0.0091(8) C18 0.0327(10) 0.0355(11) 0.0200(9) 0.0051(8) 0.0022(8) 0.0049(9) C19 0.0274(9) 0.0221(9) 0.0237(9) 0.0012(7) -0.0001(8) 0.0006(7) _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 H1 0.87(2) . ? O1 C6 1.406(2) . ? O2 D1 0.82(3) . ? O2 D2 0.86(3) . ? N1 C1 1.334(2) . ? N1 C2 1.474(2) . ? N1 C5 1.365(2) . ? N2 N3 1.3830(19) . ? N2 C5 1.305(2) . ? N3 C1 1.333(2) . ? N3 C14 1.439(2) . ? C1 C6 1.519(2) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C2 C3 1.544(2) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C3 C4 1.548(2) . ? C4 H4A 0.9899 . ? C4 H4B 0.9900 . ? C4 C5 1.488(2) . ? C6 H6 1.0001 . ? C6 C7 1.519(2) . ? C7 C8 1.392(2) . ? C7 C12 1.390(2) . ? C8 H8 0.9498 . ? C8 C9 1.386(2) . ? C9 H9 0.9502 . ? C9 C10 1.375(3) . ? C10 C11 1.378(3) . ? C10 F 1.357(2) . ? C11 H11 0.9501 . ? C11 C12 1.388(3) . ? C12 H12 0.9499 . ? C14 C15 1.383(2) . ? C14 C19 1.378(2) . ? C15 H15 0.9500 . ? C15 C16 1.388(3) . ? C16 H16 0.9500 . ? C16 C17 1.387(3) . ? C17 H17 0.9498 . ? C17 C18 1.386(3) . ? C18 H18 0.9502 . ? C18 C19 1.388(3) . ? C19 H19 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 C6 O1 H1 106.2(15) . . ? D1 O2 D2 107(3) . . ? C1 N1 C2 138.80(14) . . ? C1 N1 C5 107.69(14) . . ? C5 N1 C2 113.21(13) . . ? C5 N2 N3 102.56(13) . . ? N2 N3 C14 120.26(13) . . ? C1 N3 N2 112.60(13) . . ? C1 N3 C14 127.13(14) . . ? N1 C1 C6 128.09(15) . . ? N3 C1 N1 105.16(14) . . ? N3 C1 C6 126.69(14) . . ? N1 C2 H2A 111.6 . . ? N1 C2 H2B 111.6 . . ? N1 C2 C3 101.01(13) . . ? H2A C2 H2B 109.4 . . ? C3 C2 H2A 111.6 . . ? C3 C2 H2B 111.5 . . ? C2 C3 H3A 110.2 . . ? C2 C3 H3B 110.2 . . ? C2 C3 C4 107.44(14) . . ? H3A C3 H3B 108.5 . . ? C4 C3 H3A 110.2 . . ? C4 C3 H3B 110.2 . . ? C3 C4 H4A 111.4 . . ? C3 C4 H4B 111.4 . . ? H4A C4 H4B 109.3 . . ? C5 C4 C3 101.53(14) . . ? C5 C4 H4A 111.5 . . ? C5 C4 H4B 111.5 . . ? N1 C5 C4 111.52(14) . . ? N2 C5 N1 111.99(15) . . ? N2 C5 C4 136.46(16) . . ? O1 C6 C1 109.80(13) . . ? O1 C6 H6 109.2 . . ? O1 C6 C7 109.44(13) . . ? C1 C6 H6 109.2 . . ? C1 C6 C7 109.96(13) . . ? C7 C6 H6 109.2 . . ? C8 C7 C6 119.71(15) . . ? C12 C7 C6 120.82(15) . . ? C12 C7 C8 119.48(16) . . ? C7 C8 H8 119.9 . . ? C9 C8 C7 120.32(16) . . ? C9 C8 H8 119.8 . . ? C8 C9 H9 120.7 . . ? C10 C9 C8 118.67(16) . . ? C10 C9 H9 120.7 . . ? C9 C10 C11 122.68(16) . . ? F C10 C9 118.76(16) . . ? F C10 C11 118.55(16) . . ? C10 C11 H11 120.9 . . ? C10 C11 C12 118.10(17) . . ? C12 C11 H11 121.0 . . ? C7 C12 H12 119.7 . . ? C11 C12 C7 120.74(17) . . ? C11 C12 H12 119.6 . . ? C15 C14 N3 119.21(15) . . ? C19 C14 N3 118.43(15) . . ? C19 C14 C15 122.35(16) . . ? C14 C15 H15 120.8 . . ? C14 C15 C16 118.25(17) . . ? C16 C15 H15 120.9 . . ? C15 C16 H16 119.9 . . ? C17 C16 C15 120.32(17) . . ? C17 C16 H16 119.8 . . ? C16 C17 H17 119.8 . . ? C18 C17 C16 120.36(17) . . ? C18 C17 H17 119.8 . . ? C17 C18 H18 120.1 . . ? C17 C18 C19 119.83(17) . . ? C19 C18 H18 120.1 . . ? C14 C19 C18 118.86(17) . . ? C14 C19 H19 120.6 . . ? C18 C19 H19 120.6 . . ? 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 O1 H1 Cl 0.87(2) 2.17(2) 3.0413(14) 175(2) . O2 D1 Cl 0.82(3) 2.40(3) 3.2206(18) 173(3) 5_566 O2 D2 Cl 0.86(3) 2.35(3) 3.184(2) 162(3) . #===END