#------------------------------------------------------------------------------ #$Date: 2025-08-19 07:12:48 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301798 $ #$URL: svn://www.crystallography.net/cod/cif/2/01/11/2011145.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_2011145 loop_ _publ_author_name 'Pani, Marcella' 'Mugnoli, Angelo' 'Sottofattori, Enzo' _publ_section_title ; 7-Chloro-3,6-dimethyl-1H-indene-2-carbaldehyde ; _journal_issue 7 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 840 _journal_page_last 842 _journal_paper_doi 10.1107/S010827010000442X _journal_volume 56 _journal_year 2000 _chemical_formula_moiety 'C12 H11 Cl O' _chemical_formula_sum 'C12 H11 Cl O' _chemical_formula_weight 206.7 _chemical_melting_point 438 _chemical_name_systematic 7-Chloro-3,6-dimethyl-1H-indene-2-carbaldehyde _space_group_IT_number 9 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall 'I -2ya' _symmetry_space_group_name_H-M 'I 1 a 1' _cell_angle_alpha 90.00 _cell_angle_beta 106.12(2) _cell_angle_gamma 90.00 _cell_formula_units_Z 4.00 _cell_length_a 7.146(2) _cell_length_b 19.751(4) _cell_length_c 7.4080(10) _cell_measurement_reflns_used 25 _cell_measurement_temperature 294(2) _cell_measurement_theta_max 20.7 _cell_measurement_theta_min 17.3 _cell_volume 1004.5(4) _computing_cell_refinement 'CAD-4 Software' _computing_data_collection 'CAD-4 Software (Enraf-Nonius, 1989)' _computing_data_reduction 'CADABS (local software)' _computing_molecular_graphics 'ORTEPII (Johnson, 1976) and PLUTO (Motherwell & Clegg, 1978)' _computing_publication_material 'PARST (Nardelli, 1983, 1995) and PARSTCIF (Nardelli, 1991)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _diffrn_ambient_temperature 294(2) _diffrn_measured_fraction_theta_full .498 _diffrn_measured_fraction_theta_max .498 _diffrn_measurement_device_type 'Enraf-Nonius CAD-4 diffractometer' _diffrn_measurement_method '\w-2\q scan mode' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength .7107 _diffrn_reflns_av_R_equivalents .0041 _diffrn_reflns_av_sigmaI/netI .0195 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_number 2300 _diffrn_reflns_theta_full 27.45 _diffrn_reflns_theta_max 27.45 _diffrn_reflns_theta_min 3.04 _diffrn_standards_decay_% 0 _diffrn_standards_interval_time 150 _diffrn_standards_number 2 _exptl_absorpt_coefficient_mu .341 _exptl_absorpt_correction_T_max .909 _exptl_absorpt_correction_T_min .698 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_process_details '(North et al., 1968)' _exptl_crystal_colour 'light yellow' _exptl_crystal_density_diffrn 1.367 _exptl_crystal_density_method 'not measured' _exptl_crystal_description 'trapezoidal irregular prism' _exptl_crystal_F_000 432.0 _exptl_crystal_size_max .52 _exptl_crystal_size_mid .44 _exptl_crystal_size_min .28 _refine_diff_density_max .375 _refine_diff_density_min -.295 _refine_ls_abs_structure_details 'Flack (1983)' _refine_ls_abs_structure_Flack -.03(5) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.071 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 151 _refine_ls_number_reflns 2289 _refine_ls_number_restraints 2 _refine_ls_R_factor_all .0407 _refine_ls_R_factor_gt .0382 _refine_ls_shift/su_max .002 _refine_ls_shift/su_mean .000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details ' w = 1/[\s^2^(Fo^2^)+(0.0723P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref .0951 _reflns_number_gt 2140 _reflns_number_total 2289 _reflns_threshold_expression 'Fo > 4 \s(Fo)' _cod_data_source_file na1467.cif _cod_data_source_block III _cod_depositor_comments ; Changing the _atom_site_occupancy data item value from '.' to '1' for all fully occupied atom sites. Antanas Vaitkus, 2017-02-10 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 ; _cod_original_sg_symbol_H-M 'I a' _cod_database_code 2011145 loop_ _symmetry_equiv_pos_as_xyz x,y,z x+1/2,-y,z x+1/2,y+1/2,z+1/2 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_occupancy _atom_site_disorder_group _atom_site_type_symbol Cl .36884(9) .11600(2) .79279(8) .0528(2) Uani . 1 . Cl O1 .3884(3) -.18294(9) .8798(2) .0590(6) Uani . 1 . O C1 .3474(3) -.04515(8) .7241(2) .0354(5) Uani . 1 . C C2 .3109(3) -.11074(7) .6173(2) .0357(4) Uani . 1 . C C3 .2481(2) -.10016(8) .4295(2) .0356(5) Uani . 1 . C C4 .1791(3) .00951(9) .2304(2) .0424(6) Uani . 1 . C C5 .1818(3) .07970(10) .2410(3) .0479(6) Uani . 1 . C C6 .2408(3) .11439(8) .4112(3) .0408(6) Uani . 1 . C C7 .2969(2) .07580(8) .5758(2) .0372(5) Uani . 1 . C C8 .2949(2) .00606(8) .5699(2) .0331(5) Uani . 1 . C C9 .2364(2) -.02702(8) .3967(2) .0349(4) Uani . 1 . C C10 .3394(3) -.17630(10) .7102(3) .0446(7) Uani . 1 . C C11 .1960(3) -.15020(10) .2743(3) .0478(6) Uani . 1 . C C12 .2417(4) .19030(10) .4146(4) .0600(8) Uani . 1 . C H1A .263(4) -.0426(12) .796(4) .045(6) Uiso . 1 . H H1B .490(4) -.0399(11) .788(4) .046(6) Uiso . 1 . H H4 .133(4) -.0193(14) .112(4) .062(7) Uiso . 1 . H H5 .138(4) .1051(14) .130(4) .059(7) Uiso . 1 . H H10 .319(4) -.2159(16) .627(4) .076(8) Uiso . 1 . H H11A .223 -.195 .325 .065(4) Uiso calc 1 . H H11B .271 -.142 .188 .065(4) Uiso calc 1 . H H11C .060 -.146 .210 .065(4) Uiso calc 1 . H H12A .204 .207 .288 .092(6) Uiso calc 1 . H H12B .370 .206 .478 .092(6) Uiso calc 1 . H H12C .152 .206 .480 .092(6) Uiso calc 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 Cl .0716(3) .0390(2) .0457(2) -.0020(2) .0129(2) -.0110(2) O1 .0890(11) .0426(8) .0434(8) .0049(7) .0152(8) .0105(6) C1 .0477(9) .0288(7) .0292(6) .0024(6) .0100(6) .0000(5) C2 .0442(7) .0287(7) .0348(8) .0019(6) .0119(6) -.0006(5) C3 .0416(7) .0330(7) .0330(8) .0026(6) .0117(6) -.0017(6) C4 .0529(10) .0432(9) .0298(8) .0064(7) .0096(7) .0034(6) C5 .0579(11) .0459(10) .0408(9) .0102(8) .0151(8) .0153(8) C6 .0459(8) .0325(8) .0466(9) .0081(7) .0171(7) .0079(7) C7 .0398(7) .0357(8) .0371(8) .0028(6) .0125(6) -.0004(6) C8 .0376(7) .0327(7) .0296(8) .0039(6) .0101(6) .0021(6) C9 .0395(7) .0346(7) .0314(6) .0038(6) .0114(5) .0010(6) C10 .0600(11) .0315(9) .0426(10) .0030(7) .0143(8) .0051(7) C11 .0632(11) .0400(9) .0388(8) .0018(8) .0118(8) -.0104(7) C12 .0823(14) .0308(9) .0715(14) .0101(9) .0289(11) .0103(9) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source Cl 'Chlorine ' .1484 .1585 'Int. Tab. C, 4.2.6.8, 6.1.1.4' 'O ' 'Oxygen ' .0106 .0060 'Int. Tab. C, 4.2.6.8, 6.1.1.4' 'C ' 'Carbon ' .0033 .0016 'Int. Tab. C, 4.2.6.8, 6.1.1.4' 'H ' 'Hydrogen ' .0000 .0000 'Int. Tab. C, 4.2.6.8, 6.1.1.4' loop_ _diffrn_standard_refln_index_h _diffrn_standard_refln_index_k _diffrn_standard_refln_index_l 3 5 -4 0 13 1 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 C2 C1 C8 102.20(10) no C2 C1 H1A 108(2) no C2 C1 H1B 110.0(10) no C8 C1 H1A 110(2) no C8 C1 H1B 107.0(10) no H1A C1 H1B 118(2) no C1 C2 C3 111.60(10) no C1 C2 C10 122.50(10) yes C3 C2 C10 125.9(2) yes C2 C3 C9 108.10(10) no C2 C3 C11 129.3(2) yes C9 C3 C11 122.6(2) no C5 C4 C9 118.2(2) no C5 C4 H4 127(2) no C9 C4 H4 115.0(10) no C4 C5 C6 122.5(2) no C4 C5 H5 119(2) no C6 C5 H5 118(2) no C5 C6 C7 117.6(2) no C5 C6 C12 120.4(2) no C7 C6 C12 122.1(2) yes Cl C7 C6 119.80(10) yes Cl C7 C8 118.90(10) no C6 C7 C8 121.3(2) no C1 C8 C7 130.90(10) no C1 C8 C9 109.50(10) no C7 C8 C9 119.70(10) no C3 C9 C4 130.5(2) no C3 C9 C8 108.70(10) no C4 C9 C8 120.8(2) no O1 C10 C2 123.2(2) yes O1 C10 H10 121(2) no C2 C10 H10 116(2) no C3 C11 H11A 109.5 no C3 C11 H11B 109.5 no C3 C11 H11C 109.5 no H11A C11 H11B 109.5 no H11A C11 H11C 109.5 no H11B C11 H11C 109.5 no C6 C12 H12A 109.5 no C6 C12 H12B 109.5 no C6 C12 H12C 109.5 no H12A C12 H12B 109.5 no H12A C12 H12C 109.5 no H12B C12 H12C 109.5 no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag Cl C7 . . 1.738(2) yes O1 C10 . . 1.214(2) yes C1 C2 . . 1.503(2) no C1 C8 . . 1.494(2) no C1 H1A . . .91(3) no C1 H1B . . 1.00(2) no C2 C3 . . 1.354(2) yes C2 C10 . . 1.454(3) yes C3 C9 . . 1.463(2) no C3 C11 . . 1.483(3) no C4 C5 . . 1.389(3) no C4 C9 . . 1.388(2) no C4 H4 . . 1.02(3) no C5 C6 . . 1.393(3) no C5 H5 . . .94(3) no C6 C7 . . 1.399(3) no C6 C12 . . 1.500(3) no C7 C8 . . 1.378(2) no C8 C9 . . 1.396(2) no C10 H10 . . .98(3) no C11 H11A . . .96 no C11 H11B . . .96 no C11 H11C . . .96 no C12 H12A . . .96 no C12 H12B . . .96 no C12 H12C . . .96 no 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 C8 C1 C2 C3 .4(2) no C8 C1 C2 C10 -178.9(2) no H1A C1 C2 C3 116(2) no H1A C1 C2 C10 -63(2) no H1B C1 C2 C3 -113(2) no H1B C1 C2 C10 67(2) no C2 C1 C8 C7 179.9(2) no C2 C1 C8 C9 -.2(2) no H1A C1 C8 C7 65(2) no H1A C1 C8 C9 -115(2) no H1B C1 C8 C7 -64(2) no H1B C1 C8 C9 115(2) no C1 C2 C3 C9 -.4(2) no C1 C2 C3 C11 179.9(2) no C10 C2 C3 C9 178.9(2) no C10 C2 C3 C11 -.8(3) no C1 C2 C10 O1 2.4(3) yes C1 C2 C10 H10 -176(2) no C3 C2 C10 O1 -176.9(2) no C3 C2 C10 H10 5(2) no C2 C3 C9 C4 -179.5(2) no C2 C3 C9 C8 .3(2) no C11 C3 C9 C4 .2(3) no C11 C3 C9 C8 -180.0(2) no C2 C3 C11 H11A -5 no C2 C3 C11 H11B -125 no C2 C3 C11 H11C 115 no C9 C3 C11 H11A 176 no C9 C3 C11 H11B 56 no C9 C3 C11 H11C -65 no C9 C4 C5 C6 .5(3) no C9 C4 C5 H5 -177(2) no H4 C4 C5 C6 177(2) no H4 C4 C5 H5 0(3) no C5 C4 C9 C3 179.9(2) no C5 C4 C9 C8 .1(3) no H4 C4 C9 C3 2(2) no H4 C4 C9 C8 -177(2) no C4 C5 C6 C7 -.7(3) no C4 C5 C6 C12 179.8(2) no H5 C5 C6 C7 177(2) no H5 C5 C6 C12 -3(2) no C5 C6 C7 Cl -179.10(10) no C5 C6 C7 C8 .4(3) no C12 C6 C7 Cl .4(3) no C12 C6 C7 C8 179.9(2) no C5 C6 C12 H12A -3 no C5 C6 C12 H12B -123 no C5 C6 C12 H12C 117 no C7 C6 C12 H12A 178 no C7 C6 C12 H12B 58 no C7 C6 C12 H12C -62 no Cl C7 C8 C1 -.5(3) no Cl C7 C8 C9 179.60(10) no C6 C7 C8 C1 180.0(2) no C6 C7 C8 C9 .1(3) no C1 C8 C9 C3 -.1(2) no C1 C8 C9 C4 179.8(2) no C7 C8 C9 C3 179.8(2) no C7 C8 C9 C4 -.3(3) no loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 8950003 2 PubChem 10774690