#------------------------------------------------------------------------------ #$Date: 2025-08-18 23:52:38 +0100 (Mon, 18 Aug 2025) $ #$Revision: 301791 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/84/2008479.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_2008479 loop_ _publ_author_name 'Subramanian, E.' 'Renganayaki, S.' 'Shanmuga Sundara Raj, S.' 'Fun, Hoong-Kun' _publ_section_title ; N-Methyl-2'-nitrocinnamanilide ; _journal_issue 5 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 764 _journal_page_last 766 _journal_paper_doi 10.1107/S010827019801806X _journal_volume 55 _journal_year 1999 _chemical_formula_moiety 'C16 H14 N2 O3' _chemical_formula_sum 'C16 H14 N2 O3' _chemical_formula_weight 282.29 _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 107.54(2) _cell_angle_gamma 90.00 _cell_formula_units_Z 4 _cell_length_a 10.3870(10) _cell_length_b 10.2480(10) _cell_length_c 13.857(3) _cell_measurement_reflns_used 5465 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 33.16 _cell_measurement_theta_min 2.86 _cell_volume 1406.4(4) _computing_cell_refinement 'SAINT (Siemens, 1996a)' _computing_data_collection 'SMART (Siemens, 1996b)' _computing_data_reduction SAINT _computing_molecular_graphics SHELXTL _computing_publication_material 'SHELXTL and PARST (Nardelli, 1995)' _computing_structure_refinement SHELXTL _computing_structure_solution 'SHELXTL (Sheldrick, 1996)' _diffrn_ambient_temperature 293(2) _diffrn_measurement_device 'Siemens SMART CCD area-detector' _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 0.019 _diffrn_reflns_av_sigmaI/netI 0.0245 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_number 9043 _diffrn_reflns_theta_max 27.5 _diffrn_reflns_theta_min 2.86 _exptl_absorpt_coefficient_mu 0.094 _exptl_absorpt_correction_type none _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.333 _exptl_crystal_density_method 'not measured' _exptl_crystal_description block _exptl_crystal_F_000 592 _exptl_crystal_size_max 0.62 _exptl_crystal_size_mid 0.48 _exptl_crystal_size_min 0.40 _refine_diff_density_max 0.299 _refine_diff_density_min -0.150 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_all 1.029 _refine_ls_goodness_of_fit_obs 1.083 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 246 _refine_ls_number_reflns 3213 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.029 _refine_ls_restrained_S_obs 1.083 _refine_ls_R_factor_all 0.058 _refine_ls_R_factor_obs .044 _refine_ls_shift/esd_max <0.001 _refine_ls_shift/esd_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0578P)^2^+0.2854P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_all 0.124 _refine_ls_wR_factor_obs .113 _reflns_number_observed 2493 _reflns_number_total 3213 _reflns_observed_criterion I>2\s(I) _cod_data_source_file na1384.cif _cod_data_source_block na1384 _cod_depositor_comments ; The following automatic conversions were performed: '_refine_ls_weighting_scheme' value 'calc w = 1/[\s^2^(Fo^2^)+(0.0578P)^2^+0.2854P] 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^)+(0.0578P)^2^+0.2854P] where P = (Fo^2^+2Fc^2^)/3'. Automatic conversion script Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas ; _cod_original_cell_volume 1406.50(10) _cod_original_sg_symbol_H-M 'P 21/n' _cod_database_code 2008479 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 .0438(7) .0428(7) .0424(7) -.0008(6) .0137(6) -.0019(6) C2 .0528(8) .0516(8) .0479(8) -.0051(6) .0206(7) -.0007(6) C3 .0465(8) .0549(9) .0664(10) -.0068(7) .0213(7) -.0012(7) C4 .0478(9) .0594(9) .0613(9) -.0074(7) .0061(7) -.0052(8) C5 .0632(10) .0789(12) .0458(8) -.0114(8) .0140(7) -.0115(8) C6 .0516(9) .0684(10) .0490(8) -.0100(7) .0204(7) -.0100(7) C7 .0431(7) .0500(8) .0433(7) -.0018(6) .0146(6) -.0015(6) C8 .0441(7) .0522(8) .0423(7) -.0036(6) .0148(6) -.0014(6) C9 .0417(7) .0490(8) .0374(6) -.0005(6) .0131(6) -.0002(6) O10 .0478(6) .0899(8) .0445(6) -.0134(5) .0189(5) -.0122(5) N11 .0463(6) .0531(7) .0383(6) -.0070(5) .0153(5) -.0038(5) C12 .0578(10) .0681(11) .0468(8) -.0111(8) .0249(7) -.0082(8) C13 .0439(7) .0554(8) .0357(6) -.0013(6) .0133(6) -.0055(6) C14 .0571(9) .0641(10) .0463(8) .0062(8) .0127(7) -.0021(7) C15 .0524(10) .0912(14) .0493(9) .0129(9) .0055(7) -.0071(9) C16 .0439(9) .0988(14) .0550(9) -.0050(9) .0108(7) -.0198(9) C17 .0540(9) .0715(11) .0561(9) -.0145(8) .0223(8) -.0147(8) C18 .0472(8) .0574(8) .0393(7) -.0033(6) .0150(6) -.0053(6) N19 .0624(9) .0593(8) .0478(7) -.0096(6) .0168(6) .0003(6) O20 .0592(8) .0823(9) .0756(8) .0099(6) .0152(6) .0171(7) O21 .0932(10) .0986(11) .0755(9) -.0171(8) .0276(8) .0296(8) 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 C1 .33178(14) .62522(13) .53502(10) .0428(3) Uani d . 1 . C C2 .4437(2) .65321(15) .50253(12) .0496(3) Uani d . 1 . C C3 .5624(2) .6969(2) .56972(14) .0550(4) Uani d . 1 . C C4 .5729(2) .7123(2) .67078(14) .0585(4) Uani d . 1 . C C5 .4639(2) .6852(2) .70426(13) .0631(5) Uani d . 1 . C C6 .3439(2) .6429(2) .63700(12) .0552(4) Uani d . 1 . C C7 .20487(15) .57398(14) .46712(11) .0451(3) Uani d . 1 . C C8 .18236(15) .53833(14) .37121(11) .0458(3) Uani d . 1 . C C9 .05062(14) .48020(14) .31382(10) .0424(3) Uani d . 1 . C O10 -.03870(11) .46200(13) .35348(8) .0596(3) Uani d . 1 . O N11 .03045(12) .44785(12) .21526(8) .0453(3) Uani d . 1 . N C12 .1279(2) .4582(2) .15861(13) .0556(4) Uani d . 1 . C C13 -.09782(14) .39233(15) .16125(10) .0447(3) Uani d . 1 . C C14 -.1879(2) .4651(2) .08610(12) .0565(4) Uani d . 1 . C C15 -.3112(2) .4128(2) .03123(13) .0665(5) Uani d . 1 . C C16 -.3476(2) .2886(2) .05207(13) .0668(5) Uani d . 1 . C C17 -.2616(2) .2164(2) .12887(13) .0593(4) Uani d . 1 . C C18 -.13665(15) .2680(2) .18104(10) .0476(3) Uani d . 1 . C N19 -.04484(15) .18495(13) .25969(10) .0564(3) Uani d . 1 . N O20 .07351(13) .18101(13) .26351(10) .0735(4) Uani d . 1 . O O21 -.0946(2) .1244(2) .31456(11) .0886(5) Uani d . 1 . O H2 .4424(17) .6366(17) .4325(14) .058(5) Uiso d . 1 . H H3 .637(2) .7141(19) .5460(15) .073(6) Uiso d . 1 . H H5 .467(2) .6998(19) .7769(17) .080(6) Uiso d . 1 . H H8 .2491(18) .5502(16) .3368(13) .061(5) Uiso d . 1 . H H4 .659(2) .7419(18) .7196(14) .069(5) Uiso d . 1 . H H6 .2672(19) .6253(17) .6601(14) .065(5) Uiso d . 1 . H H7 .1355(17) .5589(16) .4979(13) .056(5) Uiso d . 1 . H H12B .207(2) .503(2) .1930(17) .090(7) Uiso d . 1 . H H12A .150(2) .375(3) .1380(19) .106(8) Uiso d . 1 . H H12C .092(3) .515(3) .096(2) .138(10) Uiso d . 1 . H H14 -.1649(19) .5567(19) .0744(14) .069(5) Uiso d . 1 . H H15 -.373(2) .463(2) -.0193(16) .078(6) Uiso d . 1 . H H16 -.455(2) .258(2) .0087(16) .087(6) Uiso d . 1 . H H17 -.285(2) .132(2) .1466(15) .073(6) Uiso d . 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 C6 C1 C2 118.08(13) ? C6 C1 C7 119.12(13) ? C2 C1 C7 122.75(13) ? C3 C2 C1 120.76(14) ? C2 C3 C4 120.24(15) ? C5 C4 C3 119.9(2) ? C4 C5 C6 120.2(2) ? C5 C6 C1 120.84(15) yes C8 C7 C1 126.37(13) yes C7 C8 C9 120.12(13) yes O10 C9 N11 120.32(13) yes O10 C9 C8 121.37(12) yes N11 C9 C8 118.31(12) yes C9 N11 C13 117.30(11) yes C9 N11 C12 126.93(13) yes C13 N11 C12 115.71(11) yes C18 C13 C14 118.07(14) ? C18 C13 N11 122.70(13) ? C14 C13 N11 119.23(14) ? C15 C14 C13 120.4(2) ? C16 C15 C14 120.5(2) ? C17 C16 C15 120.0(2) ? C16 C17 C18 119.0(2) ? C17 C18 C13 121.93(15) ? C17 C18 N19 117.29(14) ? C13 C18 N19 120.77(13) ? O21 N19 O20 125.0(2) yes O21 N19 C18 117.02(15) yes O20 N19 C18 118.00(13) 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 C1 C6 . 1.392(2) ? C1 C2 . 1.397(2) ? C1 C7 . 1.467(2) yes C2 C3 . 1.377(2) ? C3 C4 . 1.381(2) ? C4 C5 . 1.374(3) ? C5 C6 . 1.382(2) ? C7 C8 . 1.329(2) yes C8 C9 . 1.485(2) yes C9 O10 . 1.227(2) yes C9 N11 . 1.359(2) yes N11 C13 . 1.435(2) yes N11 C12 . 1.460(2) yes C13 C18 . 1.388(2) ? C13 C14 . 1.389(2) ? C14 C15 . 1.385(3) ? C15 C16 . 1.383(3) ? C16 C17 . 1.380(3) ? C17 C18 . 1.386(2) ? C18 N19 . 1.482(2) yes N19 O21 . 1.211(2) yes N19 O20 . 1.215(2) yes 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 C6 H6 O10 3_566 0.96(2) 2.49(2) 3.388(2) 155(2) yes C7 H7 O10 3_566 0.95(2) 2.56(2) 3.447(2) 155.0(10) yes C17 H17 O10 2_445 0.95(2) 2.53(2) 3.386(2) 150(2) yes loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 PubChem 100980012