#------------------------------------------------------------------------------ #$Date: 2015-03-06 09:11:11 +0200 (Fri, 06 Mar 2015) $ #$Revision: 133565 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/15/41/7154165.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_7154165 loop_ _publ_author_name 'Raveendra Babu, Kaki' 'Khan, Faiz Ahmed' _publ_section_title ; A domino reaction of tetrahalo-7,7-dimethoxybicyclo[2.2.1]heptenyl alcohols leading to indenones and a de novo synthesis of ninhydrin derivatives. ; _journal_issue 1 _journal_name_full 'Organic & biomolecular chemistry' _journal_page_first 299 _journal_page_last 308 _journal_paper_doi 10.1039/c4ob01977f _journal_volume 13 _journal_year 2015 _chemical_formula_moiety 'C20 H12 Cl4 O2' _chemical_formula_sum 'C20 H12 Cl4 O2' _chemical_formula_weight 426.10 _chemical_name_systematic '2,3-Dichloro-5-methyl-1H-inden-1-one ' _space_group_crystal_system monoclinic _space_group_IT_number 15 _space_group_name_Hall '-C 2yc' _space_group_name_H-M_alt 'C 1 2/c 1' _symmetry_space_group_name_Hall '-C 2yc' _symmetry_space_group_name_H-M 'C 1 2/c 1' _atom_sites_solution_hydrogens geom _audit_creation_method SHELXL-2013 _cell_angle_alpha 90 _cell_angle_beta 130.63(3) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 18.378(3) _cell_length_b 8.8145(3) _cell_length_c 14.806(2) _cell_measurement_temperature 293(2) _cell_volume 1820.3(9) _computing_structure_refinement 'SHELXL-2013 (Sheldrick, 2013)' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full 0.994 _diffrn_measured_fraction_theta_max 0.980 _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0260 _diffrn_reflns_av_unetI/netI 0.0322 _diffrn_reflns_laue_measured_fraction_full 0.994 _diffrn_reflns_laue_measured_fraction_max 0.980 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_number 3396 _diffrn_reflns_point_group_measured_fraction_full 0.994 _diffrn_reflns_point_group_measured_fraction_max 0.980 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 70.518 _diffrn_reflns_theta_min 5.874 _exptl_absorpt_coefficient_mu 6.015 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.56097 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.35.19 (release 27-10-2011 CrysAlis171 .NET) (compiled Oct 27 2011,15:02:11) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour Yellow _exptl_crystal_density_diffrn 1.555 _exptl_crystal_F_000 864 _exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: Dichloromethane' _exptl_crystal_size_max 0.16 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.12 _refine_diff_density_max 0.342 _refine_diff_density_min -0.247 _refine_diff_density_rms 0.048 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.036 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 119 _refine_ls_number_reflns 1717 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.036 _refine_ls_R_factor_all 0.0559 _refine_ls_R_factor_gt 0.0465 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0764P)^2^+0.8646P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1308 _refine_ls_wR_factor_ref 0.1428 _reflns_Friedel_coverage 0.000 _reflns_number_gt 1359 _reflns_number_total 1717 _reflns_threshold_expression 'I > 2\s(I)' _[local]_cod_data_source_file c4ob01977f2.cif _[local]_cod_data_source_block shelx _cod_depositor_comments 'Adding full bibliography for 7154165.cif.' _cod_database_code 7154165 _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; _shelxl_version_number 2013-4 _shelx_res_file ; TITL exp_1868 in C2/c #15 CELL 1.54184 18.3785 8.8145 14.8059 90.000 130.626 90.000 ZERR 8.00 0.0032 0.0003 0.0022 0.000 0.026 0.000 LATT 7 SYMM - X, Y, 1/2 - Z SFAC C H O CL UNIT 80 48 8 16 MERG 2 FMAP 2 PLAN 20 ACTA BOND $H L.S. 15 WGHT 0.076400 0.864600 FVAR 6.00090 CL2 4 0.105685 0.109717 0.465382 11.00000 0.15429 0.05149 = 0.07024 -0.01649 0.07672 -0.00939 CL1 4 0.113364 0.161091 0.254012 11.00000 0.16881 0.05497 = 0.08383 -0.00397 0.08820 -0.02817 C5 1 0.124089 -0.249147 0.349635 11.00000 0.10518 0.04623 = 0.05330 -0.00826 0.05666 -0.01020 O1 3 0.150243 -0.165644 0.217321 11.00000 0.12791 0.07744 = 0.07243 -0.00704 0.07774 -0.01078 C8 1 0.124441 -0.402688 0.512812 11.00000 0.10194 0.05067 = 0.06157 0.00214 0.05615 -0.00903 C4 1 0.086767 -0.181372 0.396240 11.00000 0.10277 0.04452 = 0.05425 -0.00334 0.05575 -0.00630 C9 1 0.087059 -0.257283 0.478253 11.00000 0.10703 0.05351 = 0.05944 0.00031 0.06196 -0.00345 AFIX 43 H6 2 0.062419 -0.211182 0.509849 11.00000 -1.20000 AFIX 0 C7 1 0.159992 -0.470782 0.463028 11.00000 0.11129 0.04190 = 0.07016 0.00020 0.05999 -0.00389 AFIX 43 H12 2 0.183717 -0.569274 0.484973 11.00000 -1.20000 AFIX 0 C3 1 0.049700 -0.023167 0.347461 11.00000 0.13136 0.03950 = 0.05930 -0.00612 0.07014 -0.00487 C6 1 0.160557 -0.395037 0.382337 11.00000 0.11054 0.05054 = 0.06623 -0.01069 0.06340 -0.00603 AFIX 43 H9 2 0.184955 -0.440908 0.350371 11.00000 -1.20000 AFIX 0 C2 1 0.063056 -0.006970 0.253814 11.00000 0.13249 0.04005 = 0.06358 -0.00222 0.07315 -0.01164 C10 1 0.129296 -0.485825 0.605740 11.00000 0.12020 0.07189 = 0.08328 0.02308 0.07321 0.00132 AFIX 137 H8AA 2 0.191796 -0.472848 0.682280 11.00000 -1.50000 H8AB 2 0.117406 -0.591838 0.586364 11.00000 -1.50000 H8AC 2 0.081774 -0.445669 0.607682 11.00000 -1.50000 AFIX 0 C1 1 0.119416 -0.147100 0.267712 11.00000 0.10999 0.05599 = 0.05588 -0.00742 0.06003 -0.01066 HKLF 4 REM exp_1868 in C2/c #15 REM R1 = 0.0465 for 1359 Fo > 4sig(Fo) and 0.0559 for all 1717 data REM 119 parameters refined using 0 restraints END WGHT 0.0758 0.8846 REM Highest difference peak 0.342, deepest hole -0.247, 1-sigma level 0.048 Q1 1 0.1812 0.1158 0.5079 11.00000 0.05 0.34 Q2 1 0.0441 0.1975 0.1965 11.00000 0.05 0.24 Q3 1 0.0681 0.1650 0.4276 11.00000 0.05 0.22 Q4 1 0.0833 -0.0790 0.2479 11.00000 0.05 0.20 Q5 1 0.0570 -0.0019 0.2996 11.00000 0.05 0.16 Q6 1 0.1848 -0.5900 0.6498 11.00000 0.05 0.16 Q7 1 0.1303 -0.0712 0.1989 11.00000 0.05 0.15 Q8 1 -0.0048 0.1205 0.3955 11.00000 0.05 0.14 Q9 1 0.2170 0.1544 0.3142 11.00000 0.05 0.13 Q10 1 0.1629 0.2752 0.3259 11.00000 0.05 0.13 Q11 1 0.0608 -0.0884 0.3623 11.00000 0.05 0.13 Q12 1 0.1701 -0.4043 0.6911 11.00000 0.05 0.13 Q13 1 0.1203 -0.2090 0.3099 11.00000 0.05 0.12 Q14 1 0.1998 0.2031 0.6030 11.00000 0.05 0.12 Q15 1 0.1285 -0.4397 0.5590 11.00000 0.05 0.11 Q16 1 0.1379 -0.0878 0.6405 11.00000 0.05 0.11 Q17 1 0.1231 0.0414 0.2772 11.00000 0.05 0.11 Q18 1 0.0793 -0.3413 0.4728 11.00000 0.05 0.11 Q19 1 0.1284 -0.1675 0.4194 11.00000 0.05 0.11 Q20 1 0.2163 -0.1176 0.2038 11.00000 0.05 0.11 ; _shelx_res_checksum 64219 loop_ _space_group_symop_operation_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_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp Cl2 Cl 0.10568(7) 0.10972(8) 0.46538(7) 0.0893(4) Uani 1 1 d . . Cl1 Cl 0.11336(8) 0.16109(9) 0.25401(8) 0.0981(4) Uani 1 1 d . . C5 C 0.1241(2) -0.2491(3) 0.3496(2) 0.0644(7) Uani 1 1 d . . O1 O 0.15024(18) -0.1656(3) 0.21732(19) 0.0832(7) Uani 1 1 d . . C8 C 0.1244(2) -0.4027(3) 0.5128(3) 0.0692(7) Uani 1 1 d . . C4 C 0.0868(2) -0.1814(3) 0.3962(2) 0.0637(7) Uani 1 1 d . . C9 C 0.0871(2) -0.2573(3) 0.4783(2) 0.0675(7) Uani 1 1 d . . H6 H 0.0624 -0.2112 0.5098 0.081 Uiso 1 1 calc R U C7 C 0.1600(2) -0.4708(3) 0.4630(3) 0.0738(8) Uani 1 1 d . . H12 H 0.1837 -0.5693 0.4850 0.089 Uiso 1 1 calc R U C3 C 0.0497(3) -0.0232(3) 0.3475(2) 0.0706(8) Uani 1 1 d . . C6 C 0.1606(2) -0.3950(3) 0.3823(3) 0.0714(8) Uani 1 1 d . . H9 H 0.1850 -0.4409 0.3504 0.086 Uiso 1 1 calc R U C2 C 0.0631(3) -0.0070(3) 0.2538(3) 0.0717(8) Uani 1 1 d . . C10 C 0.1293(3) -0.4858(4) 0.6057(3) 0.0865(10) Uani 1 1 d . . H8AA H 0.1918 -0.4728 0.6823 0.130 Uiso 1 1 calc R U H8AB H 0.1174 -0.5918 0.5864 0.130 Uiso 1 1 calc R U H8AC H 0.0818 -0.4457 0.6077 0.130 Uiso 1 1 calc R U C1 C 0.1194(2) -0.1471(3) 0.2677(2) 0.0694(8) Uani 1 1 d . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl2 0.1543(8) 0.0515(4) 0.0702(5) -0.0165(3) 0.0767(6) -0.0094(4) Cl1 0.1688(10) 0.0550(5) 0.0838(6) -0.0040(4) 0.0882(6) -0.0282(5) C5 0.105(2) 0.0462(12) 0.0533(13) -0.0083(11) 0.0567(14) -0.0102(13) O1 0.1279(18) 0.0774(14) 0.0724(13) -0.0070(11) 0.0777(14) -0.0108(12) C8 0.102(2) 0.0507(15) 0.0616(16) 0.0021(12) 0.0562(16) -0.0090(13) C4 0.103(2) 0.0445(13) 0.0542(14) -0.0033(10) 0.0558(15) -0.0063(12) C9 0.107(2) 0.0535(14) 0.0594(14) 0.0003(12) 0.0620(16) -0.0035(14) C7 0.111(2) 0.0419(13) 0.0702(17) 0.0002(12) 0.0600(18) -0.0039(14) C3 0.131(3) 0.0395(12) 0.0593(15) -0.0061(11) 0.0701(18) -0.0049(14) C6 0.111(2) 0.0505(14) 0.0662(16) -0.0107(12) 0.0634(17) -0.0060(14) C2 0.132(3) 0.0401(13) 0.0636(15) -0.0022(11) 0.0732(18) -0.0116(13) C10 0.120(3) 0.072(2) 0.083(2) 0.0231(16) 0.073(2) 0.0013(17) C1 0.110(2) 0.0560(15) 0.0559(14) -0.0074(12) 0.0600(16) -0.0107(14) 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' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.3639 0.7018 '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_site_symmetry_1 _geom_angle_site_symmetry_3 C6 C5 C4 120.7(2) . . C6 C5 C1 127.8(3) . . C4 C5 C1 111.5(2) . . C9 C8 C7 119.5(2) . . C9 C8 C10 120.4(3) . . C7 C8 C10 120.1(3) . . C9 C4 C5 120.6(3) . . C9 C4 C3 127.4(3) . . C5 C4 C3 112.0(2) . . C4 C9 C8 119.3(3) . . C4 C9 H6 120.4 . . C8 C9 H6 120.4 . . C6 C7 C8 121.3(3) . . C6 C7 H12 119.3 . . C8 C7 H12 119.3 . . C4 C3 C2 103.0(2) . . C4 C3 C2 116.0(2) . 2 C2 C3 C2 90.9(2) . 2 C4 C3 Cl2 110.3(2) . . C2 C3 Cl2 119.2(2) . . C2 C3 Cl2 115.78(19) 2 . C7 C6 C5 118.7(3) . . C7 C6 H9 120.7 . . C5 C6 H9 120.7 . . C1 C2 C3 106.8(2) . . C1 C2 C3 113.9(2) . 2 C3 C2 C3 88.1(2) . 2 C1 C2 Cl1 111.8(2) . . C3 C2 Cl1 117.69(18) . . C3 C2 Cl1 116.27(19) 2 . C8 C10 H8AA 109.5 . . C8 C10 H8AB 109.5 . . H8AA C10 H8AB 109.5 . . C8 C10 H8AC 109.5 . . H8AA C10 H8AC 109.5 . . H8AB C10 H8AC 109.5 . . O1 C1 C5 129.1(3) . . O1 C1 C2 125.0(3) . . C5 C1 C2 106.0(2) . . loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 Cl2 C3 1.772(3) . Cl1 C2 1.745(3) . C5 C6 1.384(4) . C5 C4 1.386(4) . C5 C1 1.467(4) . O1 C1 1.206(3) . C8 C9 1.385(4) . C8 C7 1.399(4) . C8 C10 1.509(4) . C4 C9 1.383(3) . C4 C3 1.513(4) . C9 H6 0.9300 . C7 C6 1.375(4) . C7 H12 0.9300 . C3 C2 1.564(3) . C3 C2 1.586(5) 2 C6 H9 0.9300 . C2 C1 1.537(4) . C2 C3 1.586(5) 2 C10 H8AA 0.9600 . C10 H8AB 0.9600 . C10 H8AC 0.9600 .