#------------------------------------------------------------------------------ #$Date: 2017-10-13 03:08:28 +0300 (Fri, 13 Oct 2017) $ #$Revision: 201955 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/00/72/2007205.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_2007205 loop_ _publ_author_name 'Dmitry Yu. Naumov' 'Marina A. Vasilchenko' 'Judith A. K. Howard' _publ_section_title ; The Monoclinic Form of Acetaminophen at 150K ; _journal_issue 5 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 653 _journal_page_last 655 _journal_paper_doi 10.1107/S0108270197018386 _journal_volume 54 _journal_year 1998 _chemical_formula_moiety 'C8 H9 N O2' _chemical_formula_structural 'CH3 CO NH C6H4 OH' _chemical_formula_sum 'C8 H9 N O2' _chemical_formula_weight 151.16 _chemical_melting_point 171.5(5) _chemical_name_common Acetaminophen _chemical_name_systematic 4-acetaminophenol _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' _audit_creation_method SHELXL _cell_angle_alpha 90.00 _cell_angle_beta 97.6720(10) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 7.0939(6) _cell_length_b 9.2625(8) _cell_length_c 11.6570(10) _cell_measurement_reflns_used 289 _cell_measurement_temperature 150(2) _cell_measurement_theta_max 20 _cell_measurement_theta_min 10 _cell_volume 759.09(11) _computing_cell_refinement SMART _computing_data_collection 'SMART (Siemens, 1994a)' _computing_data_reduction 'SAINT (Siemens, 1994b)' _computing_molecular_graphics 'SHELXLL (Siemens, 1994c)' _computing_publication_material SHELXL93 _computing_structure_refinement 'SHELXL93 (Sheldrick, 1993)' _computing_structure_solution 'SHELXS86 (Sheldrick, 1990)' _diffrn_ambient_temperature 150(2) _diffrn_measurement_device 'Siemens SMART CCD area-detector' _diffrn_measurement_method '\w scans' _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 0.0363 _diffrn_reflns_av_sigmaI/netI 0.0359 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_number 4122 _diffrn_reflns_theta_max 29.85 _diffrn_reflns_theta_min 6.10 _diffrn_standards_decay_% 0 _diffrn_standards_interval_count 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.096 _exptl_absorpt_correction_T_max 0.983 _exptl_absorpt_correction_T_min 0.969 _exptl_absorpt_correction_type 'integration (Siemens, 1995)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.323 _exptl_crystal_density_meas ? _exptl_crystal_density_method not_measured _exptl_crystal_description prism _exptl_crystal_F_000 320 _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.20 _refine_diff_density_max 0.265 _refine_diff_density_min -0.190 _refine_ls_extinction_coef 0.082(6) _refine_ls_extinction_method SHELXL93_(Sheldrick,_1993) _refine_ls_goodness_of_fit_all 1.185 _refine_ls_goodness_of_fit_obs 1.209 _refine_ls_hydrogen_treatment ; For H1' & H2' all parameters refined ; _refine_ls_matrix_type full _refine_ls_number_parameters 115 _refine_ls_number_reflns 1890 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.185 _refine_ls_restrained_S_obs 1.209 _refine_ls_R_factor_all 0.0671 _refine_ls_R_factor_obs .0555 _refine_ls_shift/esd_max 0.000 _refine_ls_shift/esd_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+0.6011P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_all 0.1119 _refine_ls_wR_factor_obs .1069 _reflns_number_observed 1672 _reflns_number_total 1890 _reflns_observed_criterion I>2\s(I) _cod_data_source_file av1018.cif _cod_data_source_block paracet _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: '_chemical_melting_point' value '171-172' was changed to '171.5(5)' - the average value was taken and precision was estimated. Automatic conversion script Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana The following automatic conversions were performed: '_chemical_melting_point' value '171-172' was changed to '171.5(5)' - the average value was taken and precision was estimated. '_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 The following automatic conversions were performed: '_exptl_crystal_density_meas' value 'not_measured' was changed to '?' - the value is perceived as not measured. Automatic conversion script Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas The following automatic conversions were performed: '_refine_ls_weighting_scheme' value 'calc w = 1/[\s^2^(Fo^2^)+0.6011P] where P=(Fo^2^+2Fc^2^)/3' was changed to 'calc'. New tag '_refine_ls_weighting_details' was created. The value of the new tag was set to 'w = 1/[\s^2^(Fo^2^)+0.6011P] where P=(Fo^2^+2Fc^2^)/3'. Automatic conversion script Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas ; _cod_original_sg_symbol_H-M 'P 21/n' _cod_database_code 2007205 _cod_database_fobs_code 2007205 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' 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 C1 .0203(8) .0229(8) .0218(7) -.0003(6) .0022(6) -.0002(6) C2 .0190(8) .0278(9) .0281(8) .0054(6) .0010(6) -.0019(7) C3 .0183(7) .0280(9) .0253(8) .0040(6) -.0013(6) -.0010(7) C4 .0189(7) .0194(7) .0202(7) .0002(6) .0044(5) .0034(6) C5 .0172(7) .0234(8) .0254(8) .0028(6) .0029(6) .0030(6) C6 .0169(7) .0272(9) .0238(7) .0005(6) -.0005(6) .0011(7) C7 .0235(8) .0226(8) .0229(7) .0024(6) .0065(6) .0042(6) O2 .0189(6) .0428(8) .0296(6) .0030(5) .0056(5) -.0008(6) C8 .0317(9) .0311(9) .0307(9) -.0008(8) .0084(7) -.0066(8) O1 .0204(6) .0347(7) .0293(6) .0012(5) -.0005(5) -.0108(5) N1 .0173(6) .0241(7) .0220(6) .0007(5) .0019(5) -.0013(5) loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_group _atom_site_type_symbol O1 .1649(2) .92111(14) .22312(11) .0285(3) Uani d . 1 . O H1' .052(4) .957(3) .241(2) .067(8) Uiso d . 1 . H C1 .1346(2) .8294(2) .12968(14) .0217(3) Uani d . 1 . C C2 -.0365(2) .8277(2) .05496(14) .0251(4) Uani d . 1 . C H2 -.139(2) .8907(14) .0690(3) .030 Uiso calc R 1 . H C3 -.0585(2) .7355(2) -.03939(14) .0243(4) Uani d . 1 . C H3 -.179(3) .7345(2) -.0914(11) .029 Uiso calc R 1 . H C4 .0888(2) .6438(2) -.06137(13) .0193(3) Uani d . 1 . C C5 .2581(2) .6437(2) .01497(14) .0220(3) Uani d . 1 . C H5 .357(2) .5815(14) .0024(3) .026 Uiso calc R 1 . H C6 .2800(2) .7362(2) .10954(14) .0229(4) Uani d . 1 . C H6 .397(2) .7357(2) .1618(11) .028 Uiso calc R 1 . H N1 .0528(2) .5529(2) -.15989(12) .0212(3) Uani d . 1 . N H2' -.073(3) .544(2) -.1914(18) .035(6) Uiso d . 1 . H C7 .1792(2) .4882(2) -.21942(14) .0227(3) Uani d . 1 . C O2 .3532(2) .49635(15) -.19141(11) .0302(3) Uani d . 1 . O C8 .0934(3) .4023(2) -.3234(2) .0308(4) Uani d . 1 . C H8A -.0343(18) .4292(11) -.3436(8) .046 Uiso calc R 1 . H H8B .1001(18) .3034(14) -.3055(5) .046 Uiso calc R 1 . H H8C .1611(15) .4207(12) -.3858(9) .046 Uiso calc R 1 . H 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' 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 H1' O1 C1 111.0(17) yes O1 C1 C2 122.13(14) yes C1 C2 C3 119.9(2) yes C3 C2 H2 120.05(9) no C1 C2 H2 120.05(9) no C2 C3 C4 120.89(15) yes C2 C3 H3 119.55(9) no C4 C3 H3 119.55(9) no C3 C4 C5 118.98(15) yes C3 C4 N1 116.82(14) yes C5 C4 N1 124.18(14) yes C4 C5 C6 120.09(15) yes C6 C5 H5 119.95(9) no C4 C5 H5 119.95(9) no C5 C6 C1 120.72(15) yes C5 C6 H6 119.64(9) no C1 C6 H6 119.64(9) no C6 C1 O1 118.47(14) yes C6 C1 C2 119.40(15) yes C4 N1 C7 128.41(14) yes C4 N1 H2' 116.0(13) yes H2' N1 C7 115.4(13) yes N1 C7 O2 123.2(2) yes N1 C7 C8 115.11(14) yes C7 C8 H8A 109.47(9) no C7 C8 H8B 109.47(10) no H8A C8 H8B 109.5 no C7 C8 H8C 109.47(9) no H8A C8 H8C 109.5 no H8B C8 H8C 109.5 no O2 C7 C8 121.72(15) yes loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O1 C1 . 1.375(2) yes C1 C2 . 1.396(2) yes C2 C3 . 1.385(2) yes C2 H2 . .96(2) no C3 C4 . 1.396(2) yes C3 H3 . .98(2) no C4 C5 . 1.396(2) yes C5 C6 . 1.388(2) yes C5 H5 . .93(2) no C6 C1 . 1.389(2) yes C6 H6 . .96(2) no C4 N1 . 1.420(2) yes N1 C7 . 1.346(2) yes C7 O2 . 1.236(2) yes C7 C8 . 1.509(2) yes C8 H8A . .939(13) no C8 H8B . .939(13) no C8 H8C . .939(13) no O1 H1' . .92(3) yes N1 H2' . .92(2) yes loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 1906