#------------------------------------------------------------------------------ #$Date: 2025-08-19 11:43:10 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301803 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/03/2200328.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_2200328 loop_ _publ_author_name 'Yoshinori Naruta' 'Yoshimitsu Tachi' 'Takefumi Chishiro' 'Yuichi Shimazaki' 'Fumito Tani' _publ_section_title ; 2-(Imidazol-1-yl)-4-methylphenol ; _journal_issue 6 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o550 _journal_page_last o552 _journal_paper_doi 10.1107/S1600536801008492 _journal_volume 57 _journal_year 2001 _chemical_formula_moiety 'C10 H10 N2 O' _chemical_formula_sum 'C10 H10 N2 O' _chemical_formula_weight 174.20 _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 1' _cell_angle_alpha 90 _cell_angle_beta 97.199(4) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 6.3521(7) _cell_length_b 10.4406(6) _cell_length_c 13.5230(10) _cell_measurement_reflns_used 4184 _cell_measurement_temperature 123.2 _cell_measurement_theta_max 30.5 _cell_measurement_theta_min 2.5 _cell_volume 889.77(13) _computing_data_collection 'PROCESS-AUTO (Molecular Structure Corporation, 1996)' _computing_data_reduction 'TEXSAN (Molecular Structure Corporation, 1999)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976)' _computing_publication_material TEXSAN _computing_structure_refinement TEXSAN _computing_structure_solution 'SIR88 (Burla et al., 1989)' _diffrn_measured_fraction_theta_full .9974 _diffrn_measured_fraction_theta_max .9974 _diffrn_measurement_device 'Rigaku RAXIS-RAPID Imaging Plate' _diffrn_measurement_method \w _diffrn_radiation_source 'X-ray tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength .7107 _diffrn_reflns_av_R_equivalents .029 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_number 10607 _diffrn_reflns_theta_full 30.50 _diffrn_reflns_theta_max 30.50 _diffrn_standards_decay_% 0 _diffrn_standards_interval_count none _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu .087 _exptl_absorpt_correction_type none _exptl_crystal_colour Colourless _exptl_crystal_density_diffrn 1.300 _exptl_crystal_density_method 'not measured' _exptl_crystal_description Prism _exptl_crystal_F_000 368 _exptl_crystal_size_max .34 _exptl_crystal_size_mid .24 _exptl_crystal_size_min .10 _refine_diff_density_max .38 _refine_diff_density_min -.36 _refine_ls_extinction_coef .16(2) _refine_ls_extinction_method 'Zachariasen (1967) type 2, Gaussian isotropic' _refine_ls_goodness_of_fit_ref 1.604 _refine_ls_hydrogen_treatment noref _refine_ls_matrix_type full _refine_ls_number_parameters 119 _refine_ls_number_reflns 2704 _refine_ls_R_factor_gt .0490 _refine_ls_shift/su_max .0006 _refine_ls_structure_factor_coef F^2^ _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^) + (0.06P)^2^] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref .1569 _reflns_number_gt 2439 _reflns_number_total 2704 _reflns_threshold_expression I>2\s(I) _cod_data_source_file ob6043.cif _cod_data_source_block I _cod_original_cell_volume 889.80(10) _cod_original_sg_symbol_H-M 'P 21/n' _cod_database_code 2200328 loop_ _symmetry_equiv_pos_as_xyz x,y,z 1/2-x,1/2+y,1/2-z -x,-y,-z 1/2+x,1/2-y,1/2+z 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 O1 -.27490(10) .16963(6) .33342(6) .0241(2) Uani d . 1.00 . . O N1 .09810(10) .03025(7) .32829(5) .0169(2) Uani d . 1.00 . . N N2 .01150(10) -.13166(7) .22629(6) .0233(2) Uani d . 1.00 . . N C1 -.0520(2) -.05760(8) .29573(7) .0222(2) Uani d . 1.00 . . C C2 .2115(2) -.08888(9) .21275(7) .0235(2) Uani d . 1.00 . . C C3 .26750(10) .01070(9) .27538(7) .0211(2) Uani d . 1.00 . . C C4 .08390(10) .12845(8) .40054(6) .0172(2) Uani d . 1.00 . . C C5 -.10380(10) .19957(8) .39922(7) .0192(2) Uani d . 1.00 . . C C6 -.1052(2) .30069(9) .46693(7) .0248(2) Uani d . 1.00 . . C C7 .0734(2) .32893(9) .53333(7) .0262(2) Uani d . 1.00 . . C C8 .2600(2) .25832(9) .53517(6) .0228(2) Uani d . 1.00 . . C C9 .26200(10) .15724(8) .46796(6) .0197(2) Uani d . 1.00 . . C C10 .4513(2) .28940(10) .60828(8) .0320(3) Uani d . 1.00 . . C H1 -.1880 -.0657 .3227 .0321 Uiso calc . 1.00 . . H H1o -.3615 .2447 .3157 .0321 Uiso calc . 1.00 . . H H2 .2909 -.1314 .1642 .0321 Uiso calc . 1.00 . . H H3 .3923 .0618 .2889 .0321 Uiso calc . 1.00 . . H H6 -.2373 .3515 .4623 .0321 Uiso calc . 1.00 . . H H7 .0701 .4033 .5810 .0321 Uiso calc . 1.00 . . H H9 .3901 .1050 .4670 .0321 Uiso calc . 1.00 . . H H10 .5679 .2312 .5984 .0321 Uiso calc . 1.00 . . H H11 .4196 .2775 .6737 .0321 Uiso calc . 1.00 . . H H12 .4965 .3748 .6008 .0321 Uiso calc . 1.00 . . H 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 O1 .0184(3) .0179(3) .0354(4) .0017(2) .0014(3) .0018(3) N1 .0177(4) .0134(3) .0194(4) .0004(2) .0016(3) -.0011(2) N2 .0235(4) .0169(4) .0288(4) -.0019(3) .0011(3) -.0036(3) C1 .0228(4) .0156(4) .0287(4) -.0044(3) .0052(3) -.0008(3) C2 .0209(4) .0220(4) .0274(4) .0009(3) .0020(3) -.0067(3) C3 .0160(4) .0209(4) .0263(4) .0003(3) .0027(3) -.0048(3) C4 .0214(4) .0131(3) .0175(4) .0007(3) .0042(3) .0011(3) C5 .0206(4) .0150(4) .0231(4) .0005(3) .0067(3) .0032(3) C6 .0283(5) .0199(4) .0280(5) .0048(3) .0107(4) -.0004(3) C7 .0387(6) .0201(4) .0213(4) .0007(4) .0093(4) -.0034(3) C8 .0316(5) .0212(4) .0160(4) -.0022(3) .0042(3) -.0001(3) C9 .0244(5) .0176(4) .0170(4) .0009(3) .0018(3) .0006(3) C10 .0383(6) .0362(6) .0206(4) -.0067(4) .0003(4) -.0070(4) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C .003 .002 'International_Tables_Vol_C_Table_4.2.6.8 and 6.1.1.1_1992' H H .000 .000 International_Tables_Vol_C_Table_6.1.1.2_1992 N N .031 .018 'International_Tables_Vol_C_Table_4.2.6.8 and 6.1.1.1_1992' O O .011 .006 'International_Tables_Vol_C_Table_4.2.6.8 and 6.1.1.1_1992' Cl Cl .006 .003 'International_Tables_Vol_C_Table_4.2.6.8 and 6.1.1.1_1992' 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 O1 H1o 111.1 no C1 N1 C3 107.08(7) no C1 N1 C4 127.29(8) no C3 N1 C4 125.58(7) no C1 N2 C2 105.88(8) no N1 C1 N2 111.25(8) no N1 C1 H1 123.5 no N2 C1 H1 125.2 no N2 C2 C3 109.75(8) no N2 C2 H2 120.0 no C3 C2 H2 130.2 no N1 C3 C2 106.03(8) no N1 C3 H3 120.0 no C2 C3 H3 133.9 no N1 C4 C5 119.89(8) no N1 C4 C9 119.15(8) no C5 C4 C9 120.85(8) no O1 C5 C4 119.86(8) no O1 C5 C6 122.32(8) no C4 C5 C6 117.82(8) no C5 C6 C7 120.82(9) no C5 C6 H6 116.1 no C7 C6 H6 123.1 no C6 C7 C8 121.59(8) no C6 C7 H7 119.7 no C8 C7 H7 118.7 no C7 C8 C9 117.77(9) no C7 C8 C10 120.89(9) no C9 C8 C10 121.33(9) no C4 C9 C8 121.14(9) no C4 C9 H9 118.6 no C8 C9 H9 120.3 no C8 C10 H10 109.8 no C8 C10 H11 109.9 no C8 C10 H12 111.4 no H10 C10 H11 107.5 no H10 C10 H12 109.0 no H11 C10 H12 109.2 no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O1 C5 . . 1.3520(10) yes O1 H1o . . .970 no N1 C1 . . 1.3560(10) no N1 C3 . . 1.3800(10) no N1 C4 . . 1.4270(10) yes N2 C1 . . 1.3180(10) no N2 C2 . . 1.3800(10) no C1 H1 . . .983 no C2 C3 . . 1.3600(10) no C2 H2 . . .983 no C3 H3 . . .954 no C4 C5 . . 1.4030(10) no C4 C9 . . 1.3940(10) no C5 C6 . . 1.3980(10) no C6 C7 . . 1.388(2) no C6 H6 . . .988 no C7 C8 . . 1.394(2) no C7 H7 . . 1.011 no C8 C9 . . 1.3940(10) no C8 C10 . . 1.5020(10) no C9 H9 . . .981 no C10 H10 . . .980 no C10 H11 . . .939 no C10 H12 . . .947 no loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_2 _geom_contact_publ_flag O1 N2 2.6290(10) 2_455 no O1 C3 3.3540(10) 1_455 no O1 C1 3.4480(10) 2_455 no O1 C10 3.5520(10) 4_454 no N1 C10 3.5460(10) 4_454 no N2 C5 3.4050(10) 2_445 no N2 C6 3.5070(10) 2_445 no C1 C8 3.4820(10) 3_556 no C3 C10 3.5160(10) 4_454 no C6 C10 3.599(2) 1_455 no 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 _geom_hbond_publ_flag O1 H1o N2 2_455 .97 1.662 2.6290(10) 174 yes 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion _geom_torsion_publ_flag O1 C5 C4 N1 1_555 1_555 1_555 1_555 4.10(10) no O1 C5 C4 C9 1_555 1_555 1_555 1_555 -179.74(8) no O1 C5 C6 C7 1_555 1_555 1_555 1_555 -179.88(8) no O1 C5 C6 H6 1_555 1_555 1_555 1_555 -2.2 no N1 C1 N2 C2 1_555 1_555 1_555 1_555 -.50(10) no N1 C3 C2 N2 1_555 1_555 1_555 1_555 -.30(10) no N1 C3 C2 H2 1_555 1_555 1_555 1_555 -179.0 no N1 C4 C5 C6 1_555 1_555 1_555 1_555 -175.58(8) no N1 C4 C9 C8 1_555 1_555 1_555 1_555 175.42(8) no N1 C4 C9 H9 1_555 1_555 1_555 1_555 -4.2 no N2 C1 N1 C3 1_555 1_555 1_555 1_555 .30(10) no N2 C1 N1 C4 1_555 1_555 1_555 1_555 178.03(8) no N2 C2 C3 H3 1_555 1_555 1_555 1_555 177.5 no C1 N1 C3 C2 1_555 1_555 1_555 1_555 .00(10) no C1 N1 C3 H3 1_555 1_555 1_555 1_555 -178.2 no C1 N1 C4 C5 1_555 1_555 1_555 1_555 -42.30(10) yes C1 N1 C4 C9 1_555 1_555 1_555 1_555 141.42(9) yes C1 N2 C2 C3 1_555 1_555 1_555 1_555 .50(10) no C1 N2 C2 H2 1_555 1_555 1_555 1_555 179.4 no C2 N2 C1 H1 1_555 1_555 1_555 1_555 -178.6 no C2 C3 N1 C4 1_555 1_555 1_555 1_555 -177.75(8) no C3 N1 C1 H1 1_555 1_555 1_555 1_555 178.4 no C3 N1 C4 C5 1_555 1_555 1_555 1_555 134.97(9) yes C3 N1 C4 C9 1_555 1_555 1_555 1_555 -41.30(10) yes C4 N1 C1 H1 1_555 1_555 1_555 1_555 -3.9 no C4 N1 C3 H3 1_555 1_555 1_555 1_555 4.1 no C4 C5 O1 H1o 1_555 1_555 1_555 1_555 -150.8 no C4 C5 C6 C7 1_555 1_555 1_555 1_555 -.30(10) no C4 C5 C6 H6 1_555 1_555 1_555 1_555 177.4 no C4 C9 C8 C7 1_555 1_555 1_555 1_555 .60(10) no C4 C9 C8 C10 1_555 1_555 1_555 1_555 179.73(8) no C5 C4 C9 C8 1_555 1_555 1_555 1_555 -.80(10) no C5 C4 C9 H9 1_555 1_555 1_555 1_555 179.6 no C5 C6 C7 C8 1_555 1_555 1_555 1_555 .1(2) no C5 C6 C7 H7 1_555 1_555 1_555 1_555 179.1 no C6 C5 O1 H1o 1_555 1_555 1_555 1_555 28.8 no C6 C5 C4 C9 1_555 1_555 1_555 1_555 .60(10) no C6 C7 C8 C9 1_555 1_555 1_555 1_555 -.20(10) no C6 C7 C8 C10 1_555 1_555 1_555 1_555 -179.36(9) no C7 C8 C9 H9 1_555 1_555 1_555 1_555 -179.8 no C7 C8 C10 H10 1_555 1_555 1_555 1_555 -179.2 no C7 C8 C10 H11 1_555 1_555 1_555 1_555 62.7 no C7 C8 C10 H12 1_555 1_555 1_555 1_555 -58.5 no C8 C7 C6 H6 1_555 1_555 1_555 1_555 -177.4 no C9 C8 C7 H7 1_555 1_555 1_555 1_555 -179.2 no C9 C8 C10 H10 1_555 1_555 1_555 1_555 1.6 no C9 C8 C10 H11 1_555 1_555 1_555 1_555 -116.5 no C9 C8 C10 H12 1_555 1_555 1_555 1_555 122.4 no C10 C8 C7 H7 1_555 1_555 1_555 1_555 1.6 no C10 C8 C9 H9 1_555 1_555 1_555 1_555 -.7 no H2 C2 C3 H3 1_555 1_555 1_555 1_555 -1.3 no H6 C6 C7 H7 1_555 1_555 1_555 1_555 1.6 no loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 15500558 2 PubChem 12509112