#------------------------------------------------------------------------------ #$Date: 2025-08-18 23:52:38 +0100 (Mon, 18 Aug 2025) $ #$Revision: 301791 $ #$URL: svn://www.crystallography.net/cod/cif/2/00/85/2008552.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_2008552 loop_ _publ_author_name 'T. N. Chandrakantha ' Puttaraja 'M. K. Kokila ' ' N. C. Shivaprakash ' _publ_section_title ; Ethyl 1-(2-cyanoethyl)-3,5-dimethyl-1H-indole-2-carboxylate ; _journal_issue 6 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 990 _journal_page_last 992 _journal_paper_doi 10.1107/S0108270199001973 _journal_volume 55 _journal_year 1999 _chemical_formula_moiety 'C16 H18 N2 O2' _chemical_formula_structural 'C16 H18 N2 O2' _chemical_formula_sum 'C16 H18 N2 O2' _chemical_formula_weight 270.32 _chemical_melting_point 360.15 _chemical_name_common Indole _chemical_name_systematic 'Ethyl 1-2'-Cyanoethyl-3,5-Dimethyl-2-Indolecarboxylate' _space_group_IT_number 2 _symmetry_cell_setting triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _audit_creation_method 'SHELXL & Norton Editor' _cell_angle_alpha 103.410(10) _cell_angle_beta 98.85(2) _cell_angle_gamma 99.51(2) _cell_formula_units_Z 2 _cell_length_a 5.925(2) _cell_length_b 8.3210(10) _cell_length_c 16.126(3) _cell_measurement_reflns_used 25 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 50 _cell_measurement_theta_min 10 _cell_volume 747.3(3) _computing_data_collection 'CAD4-PC (Enraf-Nonius, 1993)' _computing_data_reduction 'DATRD2 in NRCVAX (Gabe et al., 1989)' _computing_molecular_graphics 'Pluto & ORTEP (Johnson, 1965)' _computing_publication_material SHELXL93 _computing_structure_refinement 'SHELXL93 (Sheldrick, 1993)' _computing_structure_solution 'SHELXS86 (Sheldrick, 1985)' _diffrn_ambient_temperature 300 _diffrn_measurement_device 'Enraf-Nonius CAD4' _diffrn_measurement_method \w--2\q _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.5418 _diffrn_reflns_av_R_equivalents 0.0000 _diffrn_reflns_av_sigmaI/netI 0.0308 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_number 2103 _diffrn_reflns_theta_max 74.82 _diffrn_reflns_theta_min 5.57 _diffrn_standards_decay_% 0 _diffrn_standards_interval_count 100 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 0.643 _exptl_absorpt_correction_type none _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.201 _exptl_crystal_density_meas 1.190 _exptl_crystal_density_method 'flotation in potassium iodide and water' _exptl_crystal_description Needle _exptl_crystal_F_000 288 _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.25 _exptl_crystal_size_min 0.25 _refine_diff_density_max 0.158 _refine_diff_density_min -0.160 _refine_ls_extinction_method None _refine_ls_goodness_of_fit_all 1.101 _refine_ls_goodness_of_fit_obs 1.134 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 201 _refine_ls_number_reflns 2051 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.294 _refine_ls_restrained_S_obs 1.134 _refine_ls_R_factor_all 0.0855 _refine_ls_R_factor_obs .0636 _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^)+(0.1048P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_all 0.1824 _refine_ls_wR_factor_obs .1476 _reflns_number_observed 1721 _reflns_number_total 2103 _reflns_observed_criterion F^2^>2\s(F^2^) _cod_data_source_file da1055.cif _cod_data_source_block md8 _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic' 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: '_diffrn_ambient_temperature' value '300K' was changed to '300' - the value should be numeric and without a unit designator. '_chemical_melting_point' value '(87+273)' was changed to '360.15' - it was converted from degrees Celsius(C) to Kelvins(K). Automatic conversion script Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana The following automatic conversions were performed: '_diffrn_ambient_temperature' value '300K' was changed to '300' - the value should be numeric and without a unit designator. '_chemical_melting_point' value '(87+273)' was changed to '360.15' - it was converted from degrees Celsius(C) to Kelvins(K). Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana The following automatic conversions were performed: '_refine_ls_weighting_scheme' value 'calc w = 1/[\s^2^(Fo^2^)+(0.1048P)^2^] 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^)+(0.1048P)^2^] where P=(Fo^2^+2Fc^2^)/3'. Automatic conversion script Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas ; _cod_database_code 2008552 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' 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 N1 .066(2) .0576(13) .0567(13) .0134(12) .0115(12) .0120(10) C2 .064(2) .0531(14) .065(2) .0197(13) .0178(14) .0202(12) C3 .062(2) .0529(14) .060(2) .0186(13) .0151(13) .0160(12) C4 .067(2) .065(2) .065(2) .0185(15) .0088(15) .0139(13) C5 .068(2) .058(2) .081(2) .0132(15) .005(2) .0191(14) C6 .068(2) .067(2) .087(2) .013(2) .018(2) .029(2) C7 .065(2) .067(2) .064(2) .015(2) .0185(15) .0202(14) C8 .061(2) .0512(14) .062(2) .0183(13) .0106(13) .0147(12) C9 .065(2) .0513(14) .062(2) .0203(14) .0118(14) .0179(12) C10 .073(2) .0495(14) .065(2) .0129(14) .015(2) .0124(13) O11 .095(2) .0780(14) .0723(14) -.0094(13) .0039(13) .0106(11) O12 .0707(14) .0701(13) .0837(14) .0081(11) .0166(11) .0246(10) C13 .075(2) .064(2) .108(3) .010(2) .023(2) .027(2) C14 .090(3) .103(3) .145(4) .022(3) .045(3) .059(3) C15 .077(2) .062(2) .060(2) .0163(15) .0149(15) .0113(12) C16 .081(2) .067(2) .063(2) .012(2) .007(2) .0163(13) C17 .073(2) .070(2) .067(2) .017(2) .011(2) .0223(15) N18 .092(2) .074(2) .105(2) .014(2) .004(2) .028(2) C19 .074(2) .078(2) .063(2) .008(2) .016(2) .0127(14) C20 .088(3) .095(3) .090(2) -.007(2) .003(2) .023(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_thermal_displace_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_group _atom_site_type_symbol N1 .4026(4) .7691(3) .66752(14) .0607(6) Uani d . 1 . N C2 .2670(5) .7169(3) .7235(2) .0584(7) Uani d . 1 . C C3 .3803(5) .7972(3) .8089(2) .0571(7) Uani d . 1 . C C4 .7755(6) 1.0106(4) .8690(2) .0660(8) Uani d . 1 . C C5 .9624(6) 1.0952(4) .8454(2) .0700(8) Uani d . 1 . C C6 .9683(6) 1.0698(4) .7563(2) .0725(8) Uani d . 1 . C C7 .7926(5) .9659(4) .6925(2) .0639(8) Uani d . 1 . C C8 .6022(5) .8805(3) .7171(2) .0573(7) Uani d . 1 . C C9 .5911(5) .9008(3) .8048(2) .0581(7) Uani d . 1 . C C10 .0409(6) .6033(3) .6900(2) .0629(7) Uani d . 1 . C O11 -.0606(4) .5586(3) .61537(15) .0881(7) Uani d . 1 . O O12 -.0495(4) .5528(3) .75255(14) .0748(6) Uani d . 1 . O C13 -.2797(7) .4482(5) .7286(3) .0813(10) Uani d . 1 . C C14 -.3598(10) .4291(6) .8081(4) .1058(14) Uani d . 1 . C C15 .3620(6) .7088(4) .5727(2) .0667(8) Uani d . 1 . C C16 .1957(6) .7971(4) .5267(2) .0716(8) Uani d . 1 . C C17 .2643(6) .9807(4) .5530(2) .0692(8) Uani d . 1 . C N18 .3151(5) 1.1238(4) .5734(2) .0920(9) Uani d . 1 . N C19 .3031(6) .7815(4) .8906(2) .0736(8) Uani d . 1 . C C20 1.1621(7) 1.2143(5) .9127(2) .0961(11) Uani d . 1 . C H4 .7661 1.0294 .9292 .075 Uiso d . 1 . H H6 1.1123 1.1193 .7398 .068 Uiso d . 1 . H H7 .7970 .9528 .6350 .043 Uiso d . 1 . H H13A -.394(7) .503(5) .691(3) .121(14) Uiso d . 1 . H H13B -.252(7) .348(5) .692(2) .105(13) Uiso d . 1 . H H14A -.250(8) .395(6) .849(3) .129(17) Uiso d . 1 . H H14B -.418(11) .358(9) .841(4) .24(3) Uiso d . 1 . H H14C -.519(9) .374(6) .792(3) .132(16) Uiso d . 1 . H H15A .5207 .7227 .5543 .059 Uiso d . 1 . H H15B .2879 .5826 .5558 .067 Uiso d . 1 . H H16A .0340 .7672 .5442 .064 Uiso d . 1 . H H16B .1928 .7600 .4659 .080 Uiso d . 1 . H H19A .1498 .7927 .8911 .120 Uiso d . 1 . H H19B .2840 .6519 .8971 .125 Uiso d . 1 . H H19C .4209 .8497 .9390 .089 Uiso d . 1 . H H20A 1.1898 1.3269 .9064 .119 Uiso d . 1 . H H20B 1.1288 1.2260 .9651 .132 Uiso d . 1 . H H20C 1.3038 1.2026 .8944 .168 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 0.0181 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_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag C8 N1 C2 108.3(2) ? C8 N1 C15 123.3(2) ? C2 N1 C15 128.2(2) ? C3 C2 N1 108.9(2) ? C3 C2 C10 130.0(3) y N1 C2 C10 121.0(2) ? C2 C3 C9 106.7(2) ? C2 C3 C19 128.4(3) y C9 C3 C19 124.9(2) ? C5 C4 C9 120.2(3) ? C4 C5 C6 119.0(3) ? C4 C5 C20 121.3(3) ? C6 C5 C20 119.6(3) ? C7 C6 C5 122.5(3) ? C6 C7 C8 118.2(3) ? N1 C8 C7 130.7(3) ? N1 C8 C9 108.2(2) ? C7 C8 C9 121.1(3) ? C8 C9 C4 119.1(3) ? C8 C9 C3 107.9(2) ? C4 C9 C3 133.0(3) ? O11 C10 O12 122.0(3) ? O11 C10 C2 126.0(3) ? O12 C10 C2 112.0(3) ? C10 O12 C13 117.5(3) ? O12 C13 C14 108.6(4) ? N1 C15 C16 112.8(2) ? C17 C16 C15 114.1(3) ? N18 C17 C16 179.3(4) y 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 N1 C8 . 1.378(4) y N1 C2 . 1.392(3) y N1 C15 . 1.463(3) y C2 C3 . 1.391(4) ? C2 C10 . 1.451(4) ? C3 C9 . 1.416(4) ? C3 C19 . 1.486(4) y C4 C5 . 1.365(4) ? C4 C9 . 1.408(4) ? C5 C6 . 1.410(4) ? C5 C20 . 1.509(5) y C6 C7 . 1.360(4) ? C7 C8 . 1.391(4) ? C8 C9 . 1.399(4) ? C10 O11 . 1.201(3) ? C10 O12 . 1.331(3) ? O12 C13 . 1.434(4) ? C13 C14 . 1.466(6) ? C15 C16 . 1.526(4) y C16 C17 . 1.456(4) y C17 N18 . 1.134(4) ? loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 21105724 2 PubChem 12864572