#------------------------------------------------------------------------------ #$Date: 2025-08-19 11:43:10 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301803 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/25/2202557.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_2202557 loop_ _publ_author_name 'Thamotharan, S.' 'Parthasarathi, V.' 'Gupta, P.' 'Jindal, D. P.' 'Piplani, P.' 'Linden, Anthony' _publ_section_title ; N,N-Dimethyl-2-(2-naphthyloxy)acetamide monohydrate ; _journal_issue 8 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o1120 _journal_page_last o1122 _journal_paper_doi 10.1107/S1600536803014739 _journal_volume 59 _journal_year 2003 _chemical_formula_iupac 'C14 H15 N O2, H2 O' _chemical_formula_moiety 'C14 H15 N O2, H2 O' _chemical_formula_sum 'C14 H17 N O3' _chemical_formula_weight 247.29 _chemical_name_systematic ; N,N-dimethyl-2-(2-naphthyloxy)acetamide monohydrate ; _space_group_IT_number 15 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-C 2yc' _symmetry_space_group_name_H-M 'C 1 2/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 97.4569(5) _cell_angle_gamma 90.00 _cell_formula_units_Z 8 _cell_length_a 51.8464(6) _cell_length_b 5.91340(10) _cell_length_c 8.31120(10) _cell_measurement_reflns_used 3163 _cell_measurement_temperature 160(2) _cell_measurement_theta_max 27.5 _cell_measurement_theta_min 2.0 _cell_volume 2526.57(6) _computing_cell_refinement 'DENZO--SMN (Otwinowski & Minor, 1997)' _computing_data_collection 'COLLECT (Nonius, 2000)' _computing_data_reduction 'DENZO--SMN and SCALEPACK (Otwinowski & Minor, 1997)' _computing_molecular_graphics 'ORTEP-3 (Version 1.07; Farrugia, 1997)' _computing_publication_material 'SHELXL97 and PLATON (Spek, 2003)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 1997)' _diffrn_ambient_temperature 160(2) _diffrn_detector_area_resol_mean 9 _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.997 _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_method '\f and \w scans with \k offsets' _diffrn_radiation_monochromator 'horizontally mounted graphite crystal' _diffrn_radiation_source 'Nonius FR591 sealed tube generator' _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0560 _diffrn_reflns_av_sigmaI/netI 0.0332 _diffrn_reflns_limit_h_max 66 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 10 _diffrn_reflns_limit_l_min -10 _diffrn_reflns_number 26182 _diffrn_reflns_theta_full 27.48 _diffrn_reflns_theta_max 27.48 _diffrn_reflns_theta_min 2.38 _diffrn_standards_decay_% 0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.091 _exptl_absorpt_correction_type none _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.300 _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 1056 _exptl_crystal_size_max 0.25 _exptl_crystal_size_mid 0.23 _exptl_crystal_size_min 0.05 _refine_diff_density_max 0.316 _refine_diff_density_min -0.506 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.073 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 176 _refine_ls_number_reflns 2900 _refine_ls_number_restraints 9 _refine_ls_restrained_S_all 1.074 _refine_ls_R_factor_all 0.0949 _refine_ls_R_factor_gt 0.0660 _refine_ls_shift/su_max <0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.1228P)^2^+1.8212P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1887 _refine_ls_wR_factor_ref 0.2129 _reflns_number_gt 2033 _reflns_number_total 2900 _reflns_threshold_expression I>2\s(I) _cod_data_source_file cv6205.cif _cod_data_source_block I _cod_depositor_comments ; Marking attached hydrogen atoms. Antanas Vaitkus, 2017-03-21 ; _cod_original_sg_symbol_H-M 'C 2/c' _cod_database_code 2202557 _cod_database_fobs_code 2202557 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -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 _atom_site_attached_hydrogens O1W 0.01238(5) 0.3550(6) 0.4068(3) 0.1117(10) Uani d . 1 . . O 2 O11 0.11030(3) 0.3794(2) 0.34226(17) 0.0376(4) Uani d . 1 A . O 0 O13 0.06324(3) 0.4884(4) 0.3929(2) 0.0696(7) Uani d . 1 . . O 0 N14 0.06121(3) 0.8063(4) 0.2406(2) 0.0471(5) Uani d D 1 . . N 0 C1 0.15052(4) 0.4398(3) 0.2256(2) 0.0294(4) Uani d . 1 . . C 0 H1 0.1444 0.5782 0.1764 0.035 Uiso calc R 1 . . H 0 C2 0.13482(4) 0.3167(3) 0.3140(2) 0.0314(5) Uani d . 1 . . C 0 C3 0.14362(4) 0.1083(3) 0.3847(2) 0.0346(5) Uani d . 1 . . C 0 H3 0.1327 0.0246 0.4461 0.042 Uiso calc R 1 . . H 0 C4 0.16753(4) 0.0264(3) 0.3656(2) 0.0346(5) Uani d . 1 . . C 0 H4 0.1730 -0.1152 0.4123 0.042 Uiso calc R 1 . . H 0 C5 0.20995(4) 0.0742(4) 0.2571(2) 0.0368(5) Uani d . 1 . . C 0 H5 0.2160 -0.0666 0.3023 0.044 Uiso calc R 1 . . H 0 C6 0.22581(4) 0.2012(4) 0.1739(3) 0.0397(5) Uani d . 1 . . C 0 H6 0.2428 0.1484 0.1622 0.048 Uiso calc R 1 . . H 0 C7 0.21721(4) 0.4089(4) 0.1058(2) 0.0365(5) Uani d . 1 . . C 0 H7 0.2284 0.4960 0.0481 0.044 Uiso calc R 1 . . H 0 C8 0.19275(4) 0.4874(3) 0.1219(2) 0.0321(5) Uani d . 1 . . C 0 H8 0.1871 0.6284 0.0750 0.038 Uiso calc R 1 . . H 0 C9 0.17580(4) 0.3604(3) 0.2079(2) 0.0286(4) Uani d . 1 . . C 0 C10 0.18455(4) 0.1495(3) 0.2768(2) 0.0306(5) Uani d . 1 . . C 0 C12 0.10027(4) 0.5807(4) 0.2638(3) 0.0367(5) Uani d . 1 . . C 0 H121 0.0999 0.5655 0.1449 0.044 Uiso calc R 1 A . H 0 H122 0.1116 0.7105 0.3008 0.044 Uiso calc R 1 . . H 0 C13 0.07297(4) 0.6209(4) 0.3045(3) 0.0444(6) Uani d . 1 A . C 0 C15 0.07305(5) 0.9577(4) 0.1321(3) 0.0522(6) Uani d D 1 A . C 0 H151 0.0902 1.0052 0.1842 0.078 Uiso calc R 1 . . H 0 H152 0.0620 1.0910 0.1086 0.078 Uiso calc R 1 . . H 0 H153 0.0749 0.8785 0.0306 0.078 Uiso calc R 1 . . H 0 C16A 0.03528(12) 0.884(2) 0.2714(10) 0.054(2) Uani d PDU 0.67(3) A 1 C 0 H161 0.0230 0.8702 0.1718 0.081 Uiso calc PR 0.67(3) A 1 H 0 H162 0.0363 1.0426 0.3061 0.081 Uiso calc PR 0.67(3) A 1 H 0 H163 0.0293 0.7911 0.3569 0.081 Uiso calc PR 0.67(3) A 1 H 0 C16B 0.03275(10) 0.793(5) 0.238(3) 0.059(4) Uani d PDU 0.33(3) A 2 C 0 H164 0.0249 0.7330 0.1327 0.089 Uiso calc PR 0.33(3) A 2 H 0 H165 0.0258 0.9438 0.2540 0.089 Uiso calc PR 0.33(3) A 2 H 0 H166 0.0287 0.6920 0.3246 0.089 Uiso calc PR 0.33(3) A 2 H 0 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 O1W 0.0858(18) 0.153(3) 0.097(2) -0.0053(17) 0.0133(15) 0.0178(18) O11 0.0360(8) 0.0416(9) 0.0363(8) -0.0037(6) 0.0087(6) 0.0023(6) O13 0.0365(9) 0.1130(17) 0.0610(12) 0.0070(9) 0.0131(8) 0.0377(12) N14 0.0368(10) 0.0627(13) 0.0410(11) 0.0096(9) 0.0020(8) -0.0052(9) C1 0.0357(10) 0.0261(9) 0.0258(9) -0.0014(8) 0.0021(8) 0.0005(7) C2 0.0357(10) 0.0319(10) 0.0263(9) -0.0045(8) 0.0027(8) -0.0040(8) C3 0.0446(12) 0.0320(11) 0.0273(10) -0.0106(9) 0.0046(8) 0.0012(8) C4 0.0506(12) 0.0262(10) 0.0256(9) -0.0026(9) -0.0006(9) 0.0005(8) C5 0.0448(12) 0.0322(11) 0.0314(10) 0.0073(9) -0.0026(9) -0.0024(8) C6 0.0363(11) 0.0457(13) 0.0366(11) 0.0069(9) 0.0026(9) -0.0055(9) C7 0.0371(11) 0.0414(12) 0.0315(10) -0.0034(9) 0.0065(8) -0.0023(9) C8 0.0396(11) 0.0297(10) 0.0265(9) 0.0005(8) 0.0029(8) 0.0014(8) C9 0.0361(10) 0.0270(10) 0.0222(9) -0.0010(8) 0.0022(7) -0.0026(7) C10 0.0411(11) 0.0269(10) 0.0228(9) -0.0004(8) 0.0002(8) -0.0034(7) C12 0.0365(11) 0.0384(12) 0.0355(11) -0.0029(9) 0.0061(9) -0.0033(9) C13 0.0336(11) 0.0680(16) 0.0310(11) -0.0012(11) 0.0015(9) -0.0023(11) C15 0.0491(14) 0.0439(14) 0.0619(16) 0.0024(11) 0.0003(12) -0.0028(12) C16A 0.037(2) 0.074(5) 0.049(3) 0.011(2) 0.002(2) -0.008(3) C16B 0.046(5) 0.060(10) 0.071(8) 0.010(4) 0.003(5) -0.008(6) 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 C2 O11 C12 116.03(15) C13 N14 C15 122.93(19) C13 N14 C16A 124.6(5) C15 N14 C16A 112.4(5) C13 N14 C16B 111.5(9) C15 N14 C16B 121.6(7) C2 C1 C9 119.99(18) C2 C1 H1 120.0 C9 C1 H1 120.0 O11 C2 C1 125.04(18) O11 C2 C3 114.84(17) C1 C2 C3 120.12(18) C4 C3 C2 120.79(18) C4 C3 H3 119.6 C2 C3 H3 119.6 C3 C4 C10 120.99(18) C3 C4 H4 119.5 C10 C4 H4 119.5 C6 C5 C10 120.95(19) C6 C5 H5 119.5 C10 C5 H5 119.5 C5 C6 C7 120.38(19) C5 C6 H6 119.8 C7 C6 H6 119.8 C8 C7 C6 120.44(19) C8 C7 H7 119.8 C6 C7 H7 119.8 C7 C8 C9 120.70(18) C7 C8 H8 119.7 C9 C8 H8 119.7 C1 C9 C8 121.24(17) C1 C9 C10 119.98(17) C8 C9 C10 118.77(18) C5 C10 C9 118.75(18) C5 C10 C4 123.14(18) C9 C10 C4 118.09(18) O11 C12 C13 108.97(17) O11 C12 H121 109.9 C13 C12 H121 109.9 O11 C12 H122 109.9 C13 C12 H122 109.9 H121 C12 H122 108.3 O13 C13 N14 124.2(2) O13 C13 C12 120.1(2) N14 C13 C12 115.6(2) N14 C15 H151 109.5 N14 C15 H152 109.5 H151 C15 H152 109.5 N14 C15 H153 109.5 H151 C15 H153 109.5 H152 C15 H153 109.5 N14 C16A H161 109.5 N14 C16A H162 109.5 N14 C16A H163 109.5 N14 C16B H164 109.5 N14 C16B H165 109.5 H164 C16B H165 109.5 N14 C16B H166 109.5 H164 C16B H166 109.5 H165 C16B H166 109.5 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 O11 C2 . 1.373(2) ? O11 C12 . 1.423(3) ? O13 C13 . 1.227(3) ? N14 C13 . 1.331(3) ? N14 C15 . 1.461(3) ? N14 C16A . 1.474(3) ? N14 C16B . 1.475(4) ? C1 C2 . 1.374(3) ? C1 C9 . 1.418(3) ? C1 H1 . 0.9500 ? C2 C3 . 1.415(3) ? C3 C4 . 1.359(3) ? C3 H3 . 0.9500 ? C4 C10 . 1.422(3) ? C4 H4 . 0.9500 ? C5 C6 . 1.366(3) ? C5 C10 . 1.420(3) ? C5 H5 . 0.9500 ? C6 C7 . 1.401(3) ? C6 H6 . 0.9500 ? C7 C8 . 1.373(3) ? C7 H7 . 0.9500 ? C8 C9 . 1.418(3) ? C8 H8 . 0.9500 ? C9 C10 . 1.422(3) ? C12 C13 . 1.516(3) ? C12 H121 . 0.9900 ? C12 H122 . 0.9900 ? C15 H151 . 0.9800 ? C15 H152 . 0.9800 ? C15 H153 . 0.9800 ? C16A H161 . 0.9800 ? C16A H162 . 0.9800 ? C16A H163 . 0.9800 ? C16B H164 . 0.9800 ? C16B H165 . 0.9800 ? C16B H166 . 0.9800 ? 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 C15 H153 O13 6_565 0.98 2.49 3.302(3) 140 yes C16A H161 O1W 6_565 0.98 2.57 3.414(12) 144 yes C16A H162 O1W 1_565 0.98 2.43 3.283(12) 145 yes C16B H164 O1W 6_565 0.98 1.98 2.95(2) 172 no C4 H4 Cg2 6_556 0.95 2.75 3.519(2) 139 yes C8 H8 Cg1 6_565 0.95 2.70 3.440(2) 136 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 C12 O11 C2 C1 4.2(3) C12 O11 C2 C3 -175.98(16) C9 C1 C2 O11 178.49(17) C9 C1 C2 C3 -1.3(3) O11 C2 C3 C4 179.83(17) C1 C2 C3 C4 -0.4(3) C2 C3 C4 C10 1.2(3) C10 C5 C6 C7 -0.2(3) C5 C6 C7 C8 0.0(3) C6 C7 C8 C9 0.1(3) C2 C1 C9 C8 -177.87(17) C2 C1 C9 C10 2.2(3) C7 C8 C9 C1 179.87(18) C7 C8 C9 C10 -0.2(3) C6 C5 C10 C9 0.2(3) C6 C5 C10 C4 -178.42(18) C1 C9 C10 C5 179.98(17) C8 C9 C10 C5 0.0(3) C1 C9 C10 C4 -1.4(3) C8 C9 C10 C4 178.67(16) C3 C4 C10 C5 178.31(18) C3 C4 C10 C9 -0.3(3) C2 O11 C12 C13 178.56(16) C15 N14 C13 O13 -178.3(2) C16A N14 C13 O13 2.5(7) C16B N14 C13 O13 -20.6(12) C15 N14 C13 C12 2.6(3) C16A N14 C13 C12 -176.6(6) C16B N14 C13 C12 160.4(12) O11 C12 C13 O13 0.1(3) O11 C12 C13 N14 179.19(18) loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 PubChem 85876292