#------------------------------------------------------------------------------ #$Date: 2016-02-20 03:06:23 +0000 (Sat, 20 Feb 2016) $ #$Revision: 176774 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/22/2202219.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_2202219 loop_ _publ_author_name 'Palusiak, Marcin' _publ_section_title ; 4-(E)-But-1-enyl-2,6-dimethoxyphenyl nicotinate ; _journal_issue 6 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o854 _journal_page_last o856 _journal_paper_doi 10.1107/S1600536803010766 _journal_volume 59 _journal_year 2003 _chemical_formula_iupac 'C18 H19 N O4' _chemical_formula_moiety 'C18 H19 N O4' _chemical_formula_sum 'C18 H19 N O4' _chemical_formula_weight 313.34 _chemical_name_common ; 4-(E)-But-1-enyl-2,6-dimethoxyphenyl nicotinate ; _chemical_name_systematic ; 4-(E)-But-1-enyl-2,6-dimethoxyphenyl pyridine-3-carboxylate ; _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 98.47(2) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 9.105(2) _cell_length_b 22.729(3) _cell_length_c 8.157(3) _cell_measurement_reflns_used 20 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 13.180 _cell_measurement_theta_min 9.855 _cell_volume 1669.7(8) _computing_cell_refinement 'MSC/AFC Diffractometer Control Software' _computing_data_collection ; MSC/AFC Diffractometer Control Software (Molecular Structure Corporation, 1989) ; _computing_data_reduction 'TEXSAN (Molecular Structure Corporation, 1989)' _computing_molecular_graphics 'PLATON (Spek, 1998)' _computing_publication_material 'PARST97 (Nardelli, 1996)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS86 (Sheldrick, 1990)' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full 0.973 _diffrn_measured_fraction_theta_max 0.973 _diffrn_measurement_device_type 'Rigaku AFC-5S' _diffrn_measurement_method \w _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 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0919 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 2927 _diffrn_reflns_theta_full 67.49 _diffrn_reflns_theta_max 67.49 _diffrn_reflns_theta_min 3.89 _diffrn_standards_decay_% <2 _diffrn_standards_interval_count 150 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.723 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.247 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description needle _exptl_crystal_F_000 664 _exptl_crystal_size_max 0.430 _exptl_crystal_size_mid 0.150 _exptl_crystal_size_min 0.080 _refine_diff_density_max 0.258 _refine_diff_density_min -0.140 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.031 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 208 _refine_ls_number_reflns 2927 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.031 _refine_ls_R_factor_all 0.1029 _refine_ls_R_factor_gt 0.0390 _refine_ls_shift/su_max <0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details ; [exp(4(sin\q/\l)^2^)]/ [\s^2^(Fo^2^)+(0.0485P)^2^] where P = 0.33333Fo^2^ + 0.66667Fc^2^ ; _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0918 _refine_ls_wR_factor_ref 0.1009 _reflns_number_gt 1259 _reflns_number_total 2927 _reflns_threshold_expression I>2\s(I) _cod_data_source_file wn6157.cif _cod_data_source_block I _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 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_sg_symbol_H-M 'P 21/c' _cod_database_code 2202219 _cod_database_fobs_code 2202219 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 O31 0.20148(16) 0.10903(7) 0.47890(14) 0.0668(4) Uani d . 1 . . O O32 0.40686(16) 0.04210(7) 0.65119(16) 0.0737(4) Uani d . 1 . . O O30 -0.00077(17) 0.07045(7) 0.56448(16) 0.0771(5) Uani d . 1 . . O C35 0.2795(3) 0.19614(10) 0.8588(2) 0.0692(6) Uani d . 1 . . C H35 0.2478 0.2307 0.9034 0.083 Uiso calc R 1 . . H C3 0.0136(2) 0.07544(8) 0.2751(2) 0.0523(5) Uani d . 1 . . C O36 0.10011(19) 0.20604(7) 0.60749(17) 0.0815(5) Uani d . 1 . . O C36 0.2110(2) 0.17725(10) 0.7044(2) 0.0618(6) Uani d . 1 . . C C33 0.4404(2) 0.11191(10) 0.8818(2) 0.0647(6) Uani d . 1 . . C H33 0.5169 0.0901 0.9410 0.078 Uiso calc R 1 . . H C34 0.3942(2) 0.16426(10) 0.9475(2) 0.0647(6) Uani d . 1 . . C C2 -0.1282(2) 0.05528(10) 0.2252(2) 0.0654(6) Uani d . 1 . . C H2 -0.1840 0.0445 0.3070 0.079 Uiso calc R 1 . . H N1 -0.1910(2) 0.05014(9) 0.0680(2) 0.0763(6) Uani d . 1 . . N C31 0.2591(2) 0.12577(10) 0.6407(2) 0.0594(6) Uani d . 1 . . C C32 0.3720(2) 0.09236(10) 0.7276(2) 0.0595(6) Uani d . 1 . . C C30 0.0663(2) 0.08356(9) 0.4539(2) 0.0553(5) Uani d . 1 . . C C4 0.0996(2) 0.08932(9) 0.1534(2) 0.0637(6) Uani d . 1 . . C H4 0.1969 0.1024 0.1815 0.076 Uiso calc R 1 . . H C5 0.0366(3) 0.08318(10) -0.0106(2) 0.0705(6) Uani d . 1 . . C H5 0.0915 0.0915 -0.0954 0.085 Uiso calc R 1 . . H C40 0.4667(3) 0.18770(11) 1.1075(3) 0.0824(7) Uani d . 1 . . C H40 0.4261 0.2222 1.1429 0.099 Uiso calc R 1 . . H C6 -0.1064(3) 0.06485(10) -0.0462(3) 0.0737(7) Uani d . 1 . . C H6 -0.1482 0.0624 -0.1571 0.088 Uiso calc R 1 . . H C50 0.5790(3) 0.16676(12) 1.2051(3) 0.0940(8) Uani d . 1 . . C H50 0.6169 0.1310 1.1751 0.113 Uiso calc R 1 . . H C320 0.5181(3) 0.00505(10) 0.7347(3) 0.0907(8) Uani d . 1 . . C H321 0.5313 -0.0284 0.6663 0.136 Uiso calc R 1 . . H H322 0.4888 -0.0081 0.8370 0.136 Uiso calc R 1 . . H H323 0.6098 0.0264 0.7576 0.136 Uiso calc R 1 . . H C60 0.6556(4) 0.19491(14) 1.3645(3) 0.1125(10) Uani d . 1 . . C H61 0.7597 0.2010 1.3564 0.135 Uiso calc R 1 . . H H62 0.6112 0.2330 1.3787 0.135 Uiso calc R 1 . . H C360 0.0277(4) 0.25154(13) 0.6809(3) 0.1189(11) Uani d . 1 . . C H361 -0.0492 0.2678 0.6005 0.178 Uiso calc R 1 . . H H362 0.0981 0.2817 0.7197 0.178 Uiso calc R 1 . . H H363 -0.0153 0.2361 0.7726 0.178 Uiso calc R 1 . . H C70 0.6432(4) 0.15872(15) 1.5069(4) 0.1374(12) Uani d . 1 . . C H71 0.6926 0.1776 1.6050 0.206 Uiso calc R 1 . . H H72 0.6884 0.1212 1.4940 0.206 Uiso calc R 1 . . H H73 0.5403 0.1532 1.5166 0.206 Uiso calc R 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 O31 0.0654(9) 0.0930(11) 0.0419(8) -0.0160(8) 0.0071(7) -0.0082(7) O32 0.0762(10) 0.0849(12) 0.0582(9) 0.0032(9) 0.0044(7) -0.0165(8) O30 0.0826(11) 0.1025(12) 0.0486(8) -0.0225(9) 0.0173(8) -0.0002(8) C35 0.0794(16) 0.0680(16) 0.0594(13) -0.0046(13) 0.0073(12) -0.0046(12) C3 0.0557(12) 0.0590(13) 0.0415(11) 0.0010(10) 0.0042(9) -0.0005(9) O36 0.0979(12) 0.0818(12) 0.0614(9) 0.0092(10) 0.0011(9) 0.0045(8) C36 0.0680(14) 0.0708(17) 0.0451(12) -0.0064(12) 0.0037(11) 0.0020(11) C33 0.0633(14) 0.0780(16) 0.0513(12) -0.0075(12) 0.0032(11) -0.0030(11) C34 0.0731(15) 0.0707(16) 0.0500(12) -0.0121(13) 0.0082(11) -0.0090(11) C2 0.0617(15) 0.0865(18) 0.0483(12) -0.0023(12) 0.0087(10) -0.0025(11) N1 0.0656(12) 0.1054(16) 0.0561(11) -0.0040(11) 0.0031(10) -0.0069(10) C31 0.0637(14) 0.0765(16) 0.0376(11) -0.0133(12) 0.0065(10) -0.0035(11) C32 0.0594(14) 0.0707(16) 0.0495(12) -0.0122(11) 0.0118(10) -0.0076(11) C30 0.0589(14) 0.0594(14) 0.0469(12) -0.0027(11) 0.0052(10) -0.0026(10) C4 0.0676(14) 0.0746(15) 0.0491(12) -0.0101(12) 0.0095(11) -0.0025(10) C5 0.0873(18) 0.0817(17) 0.0432(12) -0.0144(14) 0.0122(11) -0.0019(11) C40 0.0931(19) 0.0897(19) 0.0610(14) 0.0007(15) -0.0003(14) -0.0165(13) C6 0.0775(17) 0.0890(18) 0.0508(13) -0.0031(14) -0.0029(12) -0.0027(12) C50 0.104(2) 0.101(2) 0.0690(17) 0.0065(17) -0.0133(15) -0.0206(14) C320 0.0959(19) 0.0915(19) 0.0792(17) 0.0170(16) -0.0057(15) -0.0137(14) C60 0.134(3) 0.127(3) 0.0714(17) -0.010(2) -0.0006(17) -0.0137(18) C360 0.134(3) 0.119(3) 0.097(2) 0.049(2) -0.0041(18) -0.0084(18) C70 0.177(3) 0.154(3) 0.083(2) -0.028(3) 0.028(2) -0.015(2) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 '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 1 -1 -1 2 -1 2 3 0 6 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 C30 O31 C31 117.81(15) yes C32 O32 C320 118.58(16) yes C34 C35 C36 121.0(2) no C34 C35 H35 119.5 no C36 C35 H35 119.5 no C2 C3 C4 117.95(18) no C2 C3 C30 119.23(19) no C4 C3 C30 122.78(19) no C36 O36 C360 117.53(18) yes O36 C36 C31 116.13(19) yes O36 C36 C35 125.2(2) yes C31 C36 C35 118.7(2) no C32 C33 C34 120.0(2) no C32 C33 H33 120.0 no C34 C33 H33 120.0 no C35 C34 C33 119.51(19) no C35 C34 C40 118.6(2) no C33 C34 C40 121.9(2) no N1 C2 C3 124.6(2) yes N1 C2 H2 117.7 no C3 C2 H2 117.7 no C2 N1 C6 116.1(2) yes C36 C31 C32 121.66(19) no C36 C31 O31 119.4(2) yes C32 C31 O31 118.7(2) yes O32 C32 C31 115.52(18) yes O32 C32 C33 125.3(2) yes C31 C32 C33 119.1(2) no O30 C30 O31 123.18(17) yes O30 C30 C3 125.7(2) yes O31 C30 C3 111.08(17) yes C5 C4 C3 118.1(2) no C5 C4 H4 120.9 no C3 C4 H4 120.9 no C6 C5 C4 119.1(2) no C6 C5 H5 120.5 no C4 C5 H5 120.5 no C50 C40 C34 128.6(3) no C50 C40 H40 115.7 no C34 C40 H40 115.7 no N1 C6 C5 124.1(2) no N1 C6 H6 117.9 no C5 C6 H6 117.9 no C40 C50 C60 126.4(3) no C40 C50 H50 116.8 no C60 C50 H50 116.8 no O32 C320 H321 109.5 no O32 C320 H322 109.5 no H321 C320 H322 109.5 no O32 C320 H323 109.5 no H321 C320 H323 109.5 no H322 C320 H323 109.5 no C70 C60 C50 111.6(3) no C70 C60 H61 109.3 no C50 C60 H61 109.3 no C70 C60 H62 109.3 no C50 C60 H62 109.3 no H61 C60 H62 108.0 no O36 C360 H361 109.5 no O36 C360 H362 109.5 no H361 C360 H362 109.5 no O36 C360 H363 109.5 no H361 C360 H363 109.5 no H362 C360 H363 109.5 no C60 C70 H71 109.5 no C60 C70 H72 109.5 no H71 C70 H72 109.5 no C60 C70 H73 109.5 no H71 C70 H73 109.5 no H72 C70 H73 109.5 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 O31 C30 . 1.348(2) yes O31 C31 . 1.399(2) yes O32 C32 . 1.361(2) yes O32 C320 . 1.413(2) yes O30 C30 . 1.199(2) yes C35 C34 . 1.384(3) no C35 C36 . 1.389(3) no C35 H35 . 0.9300 no C3 C2 . 1.373(3) no C3 C4 . 1.388(3) no C3 C30 . 1.478(3) no O36 C36 . 1.356(2) yes O36 C360 . 1.407(3) yes C36 C31 . 1.378(3) no C33 C32 . 1.392(3) no C33 C34 . 1.395(3) no C33 H33 . 0.9300 no C34 C40 . 1.473(3) no C2 N1 . 1.330(2) yes C2 H2 . 0.9300 no N1 C6 . 1.336(3) yes C31 C32 . 1.386(3) no C4 C5 . 1.383(3) no C4 H4 . 0.9300 no C5 C6 . 1.357(3) no C5 H5 . 0.9300 no C40 C50 . 1.291(3) no C40 H40 . 0.9300 no C6 H6 . 0.9300 no C50 C60 . 1.523(3) no C50 H50 . 0.9300 no C320 H321 . 0.9600 no C320 H322 . 0.9600 no C320 H323 . 0.9600 no C60 C70 . 1.441(4) no C60 H61 . 0.9700 no C60 H62 . 0.9700 no C360 H361 . 0.9600 no C360 H362 . 0.9600 no C360 H363 . 0.9600 no C70 H71 . 0.9600 no C70 H72 . 0.9600 no C70 H73 . 0.9600 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 C35 H35 O36 4_566 0.93 2.70 3.564(3) 154 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 _geom_torsion_publ_flag C360 O36 C36 C31 167.2(2) yes C360 O36 C36 C35 -13.9(3) yes C34 C35 C36 O36 -178.69(19) yes C34 C35 C36 C31 0.2(3) no C36 C35 C34 C33 -0.9(3) no C36 C35 C34 C40 177.5(2) no C32 C33 C34 C35 0.5(3) no C32 C33 C34 C40 -177.9(2) no C4 C3 C2 N1 -2.6(3) no C30 C3 C2 N1 175.2(2) no C3 C2 N1 C6 1.4(3) no O36 C36 C31 C32 179.86(18) yes C35 C36 C31 C32 0.8(3) no O36 C36 C31 O31 5.2(3) yes C35 C36 C31 O31 -173.83(18) yes C30 O31 C31 C36 -79.5(2) yes C30 O31 C31 C32 105.7(2) yes C320 O32 C32 C31 -178.25(19) yes C320 O32 C32 C33 2.1(3) yes C36 C31 C32 O32 179.06(18) yes O31 C31 C32 O32 -6.2(3) yes C36 C31 C32 C33 -1.2(3) no O31 C31 C32 C33 173.48(17) yes C34 C33 C32 O32 -179.8(2) no C34 C33 C32 C31 0.5(3) no C31 O31 C30 O30 -6.2(3) yes C31 O31 C30 C3 172.84(18) yes C2 C3 C30 O30 5.1(3) yes C4 C3 C30 O30 -177.2(2) yes C2 C3 C30 O31 -173.82(18) no C4 C3 C30 O31 3.8(3) no C2 C3 C4 C5 1.3(3) no C30 C3 C4 C5 -176.39(19) no C3 C4 C5 C6 1.0(3) no C35 C34 C40 C50 -176.4(3) no C33 C34 C40 C50 2.0(4) no C2 N1 C6 C5 1.2(4) no C4 C5 C6 N1 -2.4(4) no C34 C40 C50 C60 176.0(2) no C40 C50 C60 C70 117.0(4) yes