#------------------------------------------------------------------------------ #$Date: 2013-12-28 13:58:47 +0000 (Sat, 28 Dec 2013) $ #$Revision: 91933 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/43/2204366.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided by IUCr Journals, http://journals.iucr.org/. # # The file may be used within the scientific community so long as # proper attribution is given to the journal article from which the # data were obtained. # data_2204366 loop_ _publ_author_name 'Stumpf, Silvia' 'Wagner, Matthias' 'Bolte, Michael' _publ_section_title ; 4-Hydroxymethyl-3,5-dimethyl-1H-pyrazole chloroform solvate ; _journal_issue 10 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o1754 _journal_page_last o1755 _journal_volume 60 _journal_year 2004 _chemical_formula_moiety 'C6 H10 N2 O, C H Cl3' _chemical_formula_sum 'C7 H11 Cl3 N2 O' _chemical_formula_weight 245.53 _chemical_name_systematic ; ; ; _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 109.44(2) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 12.423(2) _cell_length_b 7.8430(10) _cell_length_c 12.871(2) _cell_measurement_reflns_used 1700 _cell_measurement_temperature 173(2) _cell_measurement_theta_max 25 _cell_measurement_theta_min 1 _cell_volume 1182.6(3) _computing_cell_refinement 'SAINT (Siemens, 1995)' _computing_data_collection 'SMART (Siemens, 1995)' _computing_data_reduction SAINT _computing_molecular_graphics 'XP in SHELXTL (Sheldrick, 1991)' _computing_publication_material 'SHELXL97 and PLATON (Spek, 2003)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1990)' _diffrn_ambient_temperature 173(2) _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device_type 'Siemens CCD three-circle diffractometer' _diffrn_measurement_method \w _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0740 _diffrn_reflns_av_sigmaI/netI 0.0974 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 8134 _diffrn_reflns_theta_full 25.03 _diffrn_reflns_theta_max 25.03 _diffrn_reflns_theta_min 1.74 _diffrn_standards_decay_% 0 _diffrn_standards_interval_time 1200 _diffrn_standards_number 52 _exptl_absorpt_coefficient_mu 0.742 _exptl_absorpt_correction_T_max 0.9639 _exptl_absorpt_correction_T_min 0.7557 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details '(SADABS; Sheldrick, 1996)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.379 _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 504 _exptl_crystal_size_max 0.40 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.05 _refine_diff_density_max 0.431 _refine_diff_density_min -0.585 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.017 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 121 _refine_ls_number_reflns 2084 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.017 _refine_ls_R_factor_all 0.1609 _refine_ls_R_factor_gt 0.0763 _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^)+(0.0872P)^2^+1.7867P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1690 _refine_ls_wR_factor_ref 0.2104 _reflns_number_gt 1067 _reflns_number_total 2084 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file lh6273.cif _[local]_cod_data_source_block I _[local]_cod_cif_authors_sg_H-M 'P 21/c' _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic' according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius The following automatic conversions were performed: '_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana ; _cod_database_code 2204366 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' 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_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol N1 0.6205(4) 0.8904(6) 0.4020(3) 0.0305(11) Uani d . 1 . . N N2 0.5218(4) 0.9159(6) 0.3194(3) 0.0297(11) Uani d . 1 . . N H2 0.4601 0.9577 0.3292 0.036 Uiso calc R 1 . . H C3 0.5270(4) 0.8709(7) 0.2200(4) 0.0283(13) Uani d . 1 . . C C4 0.6377(4) 0.8123(7) 0.2398(4) 0.0253(12) Uani d . 1 . . C C5 0.6919(4) 0.8261(7) 0.3542(4) 0.0270(13) Uani d . 1 . . C C31 0.4279(5) 0.8869(9) 0.1159(4) 0.0461(16) Uani d . 1 . . C H31A 0.3844 0.9897 0.1191 0.069 Uiso d PR 0.55(6) A 1 H H31B 0.3786 0.7868 0.1071 0.069 Uiso d PR 0.55(6) A 1 H H31C 0.4556 0.8948 0.0532 0.069 Uiso d PR 0.55(6) A 1 H H31D 0.4280 0.7912 0.0672 0.069 Uiso d PR 0.45(6) A 2 H H31E 0.4338 0.9941 0.0792 0.069 Uiso d PR 0.45(6) A 2 H H31F 0.3568 0.8861 0.1331 0.069 Uiso d PR 0.45(6) A 2 H C41 0.6863(4) 0.7510(7) 0.1552(4) 0.0297(13) Uani d . 1 . . C H41A 0.6620 0.8285 0.0909 0.036 Uiso calc R 1 . . H H41B 0.7706 0.7547 0.1863 0.036 Uiso calc R 1 . . H O41 0.6508(3) 0.5808(5) 0.1195(3) 0.0287(9) Uani d . 1 . . O H41 0.6393 0.5725 0.0516 0.034 Uiso calc R 1 . . H C51 0.8122(5) 0.7824(9) 0.4207(5) 0.0479(17) Uani d . 1 . . C H51A 0.8243 0.8028 0.4989 0.072 Uiso calc R 1 . . H H51B 0.8646 0.8536 0.3972 0.072 Uiso calc R 1 . . H H51C 0.8265 0.6620 0.4097 0.072 Uiso calc R 1 . . H C1 0.8467(5) 0.3163(9) 0.1846(6) 0.058(2) Uani d . 1 . . C H1 0.7999 0.4227 0.1659 0.070 Uiso calc R 1 . . H Cl1 0.76751(18) 0.1622(2) 0.22261(19) 0.0767(7) Uani d . 1 . . Cl Cl2 0.9727(2) 0.3640(4) 0.2885(3) 0.1264(12) Uani d . 1 . . Cl Cl3 0.87636(18) 0.2496(4) 0.06523(18) 0.0937(9) Uani d . 1 . . Cl 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 N1 0.033(3) 0.037(3) 0.020(2) -0.001(2) 0.008(2) 0.000(2) N2 0.033(3) 0.034(3) 0.024(2) 0.007(2) 0.013(2) 0.003(2) C3 0.038(3) 0.025(3) 0.023(3) -0.004(3) 0.013(2) 0.001(2) C4 0.030(3) 0.023(3) 0.024(3) -0.004(2) 0.010(2) 0.000(2) C5 0.031(3) 0.033(3) 0.018(3) 0.002(3) 0.010(2) 0.002(2) C31 0.042(4) 0.061(5) 0.030(3) 0.007(3) 0.006(3) 0.005(3) C41 0.035(3) 0.034(3) 0.024(3) -0.001(3) 0.015(2) -0.001(3) O41 0.037(2) 0.033(2) 0.0169(17) -0.0032(18) 0.0095(17) 0.0003(16) C51 0.041(4) 0.067(5) 0.032(3) 0.005(3) 0.008(3) -0.002(3) C1 0.036(4) 0.046(4) 0.089(5) 0.004(3) 0.014(4) 0.008(4) Cl1 0.0817(14) 0.0502(12) 0.1113(17) -0.0115(11) 0.0494(13) 0.0050(11) Cl2 0.0650(15) 0.137(3) 0.157(3) -0.0257(16) 0.0103(16) -0.062(2) Cl3 0.0634(13) 0.131(2) 0.0851(16) 0.0130(14) 0.0230(12) 0.0271(15) 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' 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' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag C5 N1 N2 105.3(4) y N1 N2 C3 113.0(4) y N1 N2 H2 123.5 ? C3 N2 H2 123.5 ? N2 C3 C4 105.7(4) y N2 C3 C31 122.9(5) ? C4 C3 C31 131.4(5) ? C3 C4 C5 105.5(4) y C3 C4 C41 126.1(5) ? C5 C4 C41 128.4(5) ? N1 C5 C4 110.6(4) y N1 C5 C51 120.9(4) ? C4 C5 C51 128.5(5) ? C3 C31 H31A 109.5 ? C3 C31 H31B 109.5 ? H31A C31 H31B 109.5 ? C3 C31 H31C 109.5 ? H31A C31 H31C 109.5 ? H31B C31 H31C 109.4 ? C3 C31 H31D 109.5 ? H31A C31 H31D 141.0 ? H31B C31 H31D 56.2 ? H31C C31 H31D 56.2 ? C3 C31 H31E 109.5 ? H31A C31 H31E 56.2 ? H31B C31 H31E 141.0 ? H31C C31 H31E 56.2 ? H31D C31 H31E 109.4 ? C3 C31 H31F 109.5 ? H31A C31 H31F 56.3 ? H31B C31 H31F 56.3 ? H31C C31 H31F 141.0 ? H31D C31 H31F 109.5 ? H31E C31 H31F 109.5 ? O41 C41 C4 112.3(4) ? O41 C41 H41A 109.1 ? C4 C41 H41A 109.1 ? O41 C41 H41B 109.1 ? C4 C41 H41B 109.1 ? H41A C41 H41B 107.9 ? C41 O41 H41 109.5 ? C5 C51 H51A 109.5 ? C5 C51 H51B 109.5 ? H51A C51 H51B 109.5 ? C5 C51 H51C 109.5 ? H51A C51 H51C 109.5 ? H51B C51 H51C 109.5 ? Cl2 C1 Cl1 112.7(4) ? Cl2 C1 Cl3 109.8(3) ? Cl1 C1 Cl3 109.9(4) ? Cl2 C1 H1 108.1 ? Cl1 C1 H1 108.1 ? Cl3 C1 H1 108.1 ? loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag N1 C5 1.335(6) y N1 N2 1.344(6) y N2 C3 1.349(6) y N2 H2 0.8800 ? C3 C4 1.390(7) y C3 C31 1.493(7) ? C4 C5 1.405(7) y C4 C41 1.490(7) ? C5 C51 1.493(7) ? C31 H31A 0.9789 ? C31 H31B 0.9789 ? C31 H31C 0.9791 ? C31 H31D 0.9791 ? C31 H31E 0.9790 ? C31 H31F 0.9788 ? C41 O41 1.433(6) ? C41 H41A 0.9900 ? C41 H41B 0.9900 ? O41 H41 0.8400 ? C51 H51A 0.9800 ? C51 H51B 0.9800 ? C51 H51C 0.9800 ? C1 Cl2 1.728(7) ? C1 Cl1 1.729(7) ? C1 Cl3 1.773(8) ? C1 H1 1.0000 ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA N2 H2 O41 2_655 0.88 1.97 2.830(5) 166.1 C1 H1 O41 . 1.00 2.14 3.094(7) 158.5 O41 H41 N1 4_575 0.84 1.88 2.707(5) 166.5 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 C5 N1 N2 C3 -0.2(6) N1 N2 C3 C4 -0.2(6) N1 N2 C3 C31 179.8(5) N2 C3 C4 C5 0.5(6) C31 C3 C4 C5 -179.5(6) N2 C3 C4 C41 -178.7(5) C31 C3 C4 C41 1.3(9) N2 N1 C5 C4 0.5(6) N2 N1 C5 C51 179.4(5) C3 C4 C5 N1 -0.6(6) C41 C4 C5 N1 178.5(5) C3 C4 C5 C51 -179.4(6) C41 C4 C5 C51 -0.2(9) C3 C4 C41 O41 -78.1(6) C5 C4 C41 O41 102.9(6) _cod_database_fobs_code 2204366 _journal_paper_doi 10.1107/S1600536804022317