#------------------------------------------------------------------------------ #$Date: 2015-01-23 12:30:19 +0000 (Fri, 23 Jan 2015) $ #$Revision: 130086 $ #$URL: svn://www.crystallography.net/cod/cif/2/01/21/2012146.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_2012146 loop_ _publ_author_name ' Ma\/lecka, Magdalena' ' Budzisz, El\.zbieta ' _publ_section_title ; Investigations on benz[1,2]oxaphosphinane derivatives ; _journal_issue 8 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 929 _journal_page_last 931 _journal_paper_doi 10.1107/S0108270101006734 _journal_volume 57 _journal_year 2001 _chemical_formula_moiety 'C13 H16 N O5 P' _chemical_formula_sum 'C13 H16 N O5 P' _chemical_formula_weight 297.24 _chemical_name_systematic ; 2-methoxy-3-[1(2-hydroxyethylamine)ethylidene]-2,3-dihydro-2,4-dioxo- 2\l^5^-benzo[e][1,2]oxaphosphinane ; _space_group_IT_number 19 _symmetry_cell_setting orthorhombic _symmetry_space_group_name_Hall 'P 2ac 2ab' _symmetry_space_group_name_H-M 'P 21 21 21' _audit_creation_method SHELXL-97 _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 9.3250(10) _cell_length_b 9.6620(10) _cell_length_c 15.619(2) _cell_measurement_reflns_used 25 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 30.45 _cell_measurement_theta_min 26.94 _cell_volume 1407.2(3) _computing_cell_refinement 'MSC/AFC Diffractometer Control Software' _computing_data_collection ;MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1989a) ; _computing_data_reduction 'TEXSAN (1989b)' _computing_molecular_graphics 'ORTEX (Mc Ardle, 1995)' _computing_publication_material 'PARST97 (Nardelli, 1996)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS86 (Sheldrick, 1990)' _diffrn_ambient_temperature 293(2) _diffrn_measurement_device_type 'AFC5S Rigaku' _diffrn_measurement_method '\w scan' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54178 _diffrn_reflns_av_R_equivalents .0640 _diffrn_reflns_av_sigmaI/netI .0651 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_number 8498 _diffrn_reflns_theta_full 66.02 _diffrn_reflns_theta_max 66.02 _diffrn_reflns_theta_min 5.52 _diffrn_standards_decay_% <2 _diffrn_standards_interval_time 150 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 1.919 _exptl_absorpt_correction_T_max .841 _exptl_absorpt_correction_T_min .712 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details '(De Meulenar & Tompa, 1965)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.403 _exptl_crystal_density_meas ? _exptl_crystal_description prism _exptl_crystal_F_000 624 _exptl_crystal_size_max .2 _exptl_crystal_size_mid .1 _exptl_crystal_size_min .1 _refine_diff_density_max .421 _refine_diff_density_min -.618 _refine_ls_abs_structure_details '(Flack, 1983)' _refine_ls_abs_structure_Flack .00(5) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.225 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 224 _refine_ls_number_reflns 2402 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.225 _refine_ls_R_factor_all .0853 _refine_ls_R_factor_gt .0636 _refine_ls_shift/su_max .051 _refine_ls_shift/su_mean .003 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details ; w = [1.00000exp(3.00(sin\q/\l)^2^)]/ [\s^2^(Fo^2^)+(0.1052P)^2^] where P = (Fo^2^ + 2Fc^2^)/3 ; _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref .1574 _reflns_number_gt 1664 _reflns_number_total 2402 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file na1518.cif _[local]_cod_data_source_block I _cod_depositor_comments ; The following automatic conversions were performed: '_exptl_absorpt_correction_type' value ' analytical' changed to 'analytical' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. '_refine_ls_weighting_scheme' value ' calc' changed to 'calc' 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 ; _cod_original_cell_volume 1407.40(10) _cod_database_code 2012146 _cod_database_fobs_code 2012146 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -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 1.0085(4) .6457(3) .47913(18) .0567(8) Uani d . 1 . . O P2 .99166(15) .52449(13) .41005(7) .0513(3) Uani d . 1 . . P O21 .9628(5) .3971(4) .4561(2) .0714(11) Uani d . 1 . . O O22 1.1366(4) .5232(5) .3601(2) .0696(11) Uani d . 1 . . O C23 1.2650(7) .4675(9) .4012(5) .101(2) Uani d . 1 . . C H231 1.3069 .5371 .4372 .111 Uiso calc R 1 . . H H232 1.3329 .4404 .3581 .111 Uiso calc R 1 . . H H233 1.2396 .3885 .4352 .111 Uiso calc R 1 . . H C3 .8643(5) .5872(5) .3370(3) .0480(10) Uani d . 1 . . C C4 .8479(5) .7341(5) .3302(3) .0493(11) Uani d . 1 . . C O4 .7573(4) .7897(4) .2813(2) .0639(10) Uani d . 1 . . O C5 .9452(5) .9682(6) .3623(3) .0533(12) Uani d . 1 . . C H5 .890(6) .993(6) .324(3) .059 Uiso d . 1 . . H C6 1.0258(6) 1.0587(6) .4111(4) .0665(14) Uani d . 1 . . C H6 1.025(6) 1.154(6) .402(4) .066(16) Uiso d . 1 . . H C7 1.0992(6) 1.0096(6) .4823(4) .0682(16) Uani d . 1 . . C H7 1.154(6) 1.067(5) .509(3) .055(14) Uiso d . 1 . . H C8 1.0935(6) .8733(6) .5026(4) .0619(13) Uani d . 1 . . C H8 1.155(7) .814(7) .555(4) .09(2) Uiso d . 1 . . H C9 1.0141(5) .7822(5) .4541(3) .0522(11) Uani d . 1 . . C C10 .9371(5) .8295(5) .3819(3) .0454(10) Uani d . 1 . . C C31 .7798(5) .4932(5) .2876(3) .0508(11) Uani d . 1 . . C C311 .8019(6) .3403(6) .2894(4) .0624(13) Uani d . 1 . . C H311 .8980 .3204 .3077 .057(15) Uiso calc R 1 . . H H312 .7869 .3032 .2331 .12(3) Uiso calc R 1 . . H H313 .7351 .2991 .3285 .11(2) Uiso calc R 1 . . H N32 .6769(4) .5415(5) .2383(3) .0568(11) Uani d . 1 . . N H32 .679(6) .642(7) .235(4) .068(17) Uiso d . 1 . . H C33 .5784(6) .4641(7) .1846(4) .0642(14) Uani d . 1 . . C H331 .541(7) .374(7) .214(4) .10(2) Uiso d . 1 . . H H332 .640(5) .445(5) .139(3) .043(12) Uiso d . 1 . . H C34 .4537(6) .5512(6) .1608(4) .0617(14) Uani d . 1 . . C H341 .384(5) .495(5) .118(3) .047(12) Uiso d . 1 . . H H342 .394(6) .571(5) .207(3) .052 Uiso d . 1 . . H O35 .4923(5) .6801(4) .1261(3) .0689(10) Uani d . 1 . . O H35 .541(7) .665(7) .095(4) .07(2) Uiso d . 1 . . 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 .067(2) .0493(19) .0534(14) .0048(19) -.0097(18) -.0007(13) P2 .0526(7) .0488(6) .0523(5) .0043(6) -.0049(6) -.0009(5) O21 .087(3) .054(2) .073(2) .0046(19) -.021(2) -.0007(17) O22 .057(2) .093(3) .0588(18) .014(2) -.0113(16) -.0076(19) C23 .059(4) .153(7) .090(4) .031(4) -.018(4) -.013(5) C3 .041(2) .053(3) .050(2) -.0034(19) .005(2) -.004(2) C4 .038(2) .064(3) .046(2) .000(2) .0026(19) -.001(2) O4 .064(2) .057(2) .070(2) .0018(18) -.0280(19) .0023(18) C5 .038(2) .060(3) .062(2) .002(2) -.007(2) -.002(2) C6 .058(3) .054(4) .087(3) -.005(2) -.004(3) -.004(3) C7 .059(3) .060(4) .086(3) -.003(3) -.022(3) -.020(3) C8 .055(3) .062(4) .069(3) -.003(2) -.016(3) -.010(3) C9 .040(2) .057(3) .059(2) .007(2) .000(2) -.010(2) C10 .035(2) .047(3) .054(2) .0024(18) -.0015(18) -.0028(19) C31 .039(2) .065(3) .049(2) -.003(2) .0044(18) .002(2) C311 .063(3) .057(4) .067(3) -.002(3) -.003(3) -.002(3) N32 .050(2) .061(3) .059(2) -.002(2) -.0097(18) -.0032(19) C33 .049(3) .078(4) .066(3) -.005(3) -.010(2) -.010(3) C34 .049(3) .075(4) .061(3) -.003(2) -.002(2) -.006(3) O35 .071(3) .068(3) .067(2) .001(2) -.005(2) -.0045(18) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C .0181 .0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N .0311 .0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O .0492 .0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' P P .2955 .4335 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l 4 0 0 0 4 0 0 0 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 C9 O1 P2 120.9(3) yes O21 P2 O22 113.7(2) yes O21 P2 O1 107.7(2) yes O22 P2 O1 104.9(2) yes O21 P2 C3 119.3(2) yes O22 P2 C3 105.3(2) yes O1 P2 C3 104.6(2) yes C23 O22 P2 119.6(4) yes O22 C23 H231 109.5 no O22 C23 H232 109.5 no H231 C23 H232 109.5 no O22 C23 H233 109.5 no H231 C23 H233 109.5 no H232 C23 H233 109.5 no C31 C3 C4 122.0(4) yes C31 C3 P2 120.4(4) yes C4 C3 P2 117.6(3) yes O4 C4 C3 122.7(4) yes O4 C4 C10 116.2(4) yes C3 C4 C10 121.0(4) yes C10 C5 C6 121.5(5) no C10 C5 H5 114(4) no C6 C5 H5 124(4) no C5 C6 C7 119.6(6) no C5 C6 H6 123(3) no C7 C6 H6 117(3) no C8 C7 C6 120.0(5) no C8 C7 H7 122(3) no C6 C7 H7 117(3) no C7 C8 C9 120.9(5) no C7 C8 H8 129(3) no C9 C8 H8 110(3) no O1 C9 C8 118.5(5) no O1 C9 C10 121.1(4) no C8 C9 C10 120.4(5) no C5 C10 C9 117.7(4) no C5 C10 C4 121.0(4) no C9 C10 C4 121.3(4) yes N32 C31 C3 119.6(5) yes N32 C31 C311 117.5(5) yes C3 C31 C311 122.9(4) yes C31 C311 H311 109.5 no C31 C311 H312 109.5 no H311 C311 H312 109.5 no C31 C311 H313 109.5 no H311 C311 H313 109.5 no H312 C311 H313 109.5 no C31 N32 C33 128.1(5) yes C31 N32 H32 112(3) no C33 N32 H32 120(3) no N32 C33 C34 110.4(5) yes N32 C33 H331 113(4) no C34 C33 H331 109(4) no N32 C33 H332 99(3) no C34 C33 H332 113(3) no H331 C33 H332 113(5) no O35 C34 C33 113.5(5) yes O35 C34 H341 111(2) no C33 C34 H341 110(2) no O35 C34 H342 106(3) no C33 C34 H342 113(3) no H341 C34 H342 103(4) no C34 O35 H35 105(6) no 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 C9 . 1.377(6) yes O1 P2 . 1.600(3) yes P2 O21 . 1.451(4) yes P2 O22 . 1.561(4) yes P2 C3 . 1.754(5) yes O22 C23 . 1.461(6) yes C23 H231 . .9600 no C23 H232 . .9600 no C23 H233 . .9600 no C3 C31 . 1.428(6) yes C3 C4 . 1.432(7) yes C4 O4 . 1.259(6) yes C4 C10 . 1.482(6) yes C5 C10 . 1.377(7) no C5 C6 . 1.382(8) no C5 H5 . .82(6) no C6 C7 . 1.389(8) no C6 H6 . .93(6) no C7 C8 . 1.356(9) no C7 H7 . .87(6) no C8 C9 . 1.377(7) no C8 H8 . 1.16(7) no C9 C10 . 1.413(6) yes C31 N32 . 1.316(6) yes C31 C311 . 1.492(8) yes C311 H311 . .9600 no C311 H312 . .9600 no C311 H313 . .9600 no N32 C33 . 1.451(6) yes N32 H32 . .97(6) no C33 C34 . 1.483(8) yes C33 H331 . 1.05(7) no C33 H332 . .94(5) no C34 O35 . 1.405(7) yes C34 H341 . 1.09(5) no C34 H342 . .93(5) no O35 H35 . .68(6) 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 N32 H32 O4 1_555 .97(6) 1.76(6) 2.601(6) 143(5) yes N32 H32 O35 1_555 .97(6) 2.46(6) 2.797(6) 100(4) yes O35 H35 O21 2_664 .68(6) 2.25(7) 2.790(6) 137(7) yes