# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2011 data_publication_text _journal_name_full CrystEngComm _journal_coden_cambridge 1350 _publ_contact_author_name 'Coquerel gerard' _publ_contact_author_address ;Universit\'e de Rouen Laboratoire SMS EA 3233 Rue Lucien Tesniere 76821 Mont Saint Aignan cedex France ; _publ_contact_author_email gerard.coquerel@univ-rouen.fr loop_ _publ_author_name _publ_author_address J.Mahieux ;Universit\'e de Rouen Laboratoire SMS EA 3233 Rue Lucien Tesniere 76821 Mont Saint Aignan cedex France ; S.Gonella-Burel ;Universit\'e de Rouen Laboratoire SMS EA 3233 Rue Lucien Tesniere 76821 Mont Saint Aignan cedex France ; M.Sanselme ;Universit\'e de Rouen Laboratoire SMS EA 3233 Rue Lucien Tesniere 76821 Mont Saint Aignan cedex France ; G.Coquerel ;Universit\'e de Rouen Laboratoire SMS EA 3233 Rue Lucien Tesniere 76821 Mont Saint Aignan cedex France ; _publ_requested_category FO #\#CIF_1.1 # CIF produced by WinGX routine CIF_UPDATE # Created on 2011-07-06 at 16:20:35 # Using CIFtbx version 2.6.2 16 Jun 1998 # Dictionary name : cif_core.dic # Dictionary vers : 2.3 # Request file : c:\program files\wingx\files\archive.dat # CIF files read : jm100211 struct data_jm100211 _database_code_depnum_ccdc_archive 'CCDC 818797' #TrackingRef '- CCDC818797_reviewed_archive.cif' _audit_creation_date 2011-07-06T16:20:35-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C52 H50 Cl8 N2 O8' _chemical_formula_sum 'C52 H50 Cl8 N2 O8' _chemical_formula_weight 1114.54 _chemical_compound_source 'synthesis as described' _chemical_absolute_configuration ad #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 1 2 1' _symmetry_space_group_name_Hall 'C 2y' _symmetry_Int_Tables_number 5 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y, -z' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z' _cell_length_a 25.444(2) _cell_length_b 8.0222(7) _cell_length_c 13.4912(12) _cell_angle_alpha 90 _cell_angle_beta 106.5180(10) _cell_angle_gamma 90 _cell_volume 2640.2(4) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description rod _exptl_crystal_colour colourless _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.05 _exptl_crystal_density_diffrn 1.402 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1152 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.481 _exptl_absorpt_correction_type none #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_reflns_av_R_equivalents 0.0202 _diffrn_reflns_av_unetI/netI 0.0289 _diffrn_reflns_number 10636 _diffrn_reflns_limit_h_min -31 _diffrn_reflns_limit_h_max 31 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_theta_min 1.57 _diffrn_reflns_theta_max 26.41 _diffrn_reflns_theta_full 26.41 _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.997 _reflns_number_total 5364 _reflns_number_gt 4681 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0931P)^2^+2.8747P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 5364 _refine_ls_number_parameters 317 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0739 _refine_ls_R_factor_gt 0.0657 _refine_ls_wR_factor_ref 0.1802 _refine_ls_wR_factor_gt 0.1713 _refine_ls_goodness_of_fit_ref 1.029 _refine_ls_restrained_S_all 1.029 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.01(9) _refine_diff_density_max 0.494 _refine_diff_density_min -0.481 _refine_diff_density_rms 0.068 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1A Cl 0.33672(6) 0.51162(17) 0.18870(12) 0.0870(4) Uani 1 1 d . . . Cl2A Cl 0.24659(5) 0.2501(3) 0.09742(15) 0.1227(7) Uani 1 1 d . . . O2A O 0.49988(11) 0.6006(4) 0.21717(19) 0.0622(7) Uani 1 1 d . . . O1A O 0.45044(10) 0.4344(3) 0.09685(17) 0.0540(6) Uani 1 1 d . . . C1A C 0.35432(16) 0.3021(5) 0.1904(3) 0.0583(9) Uani 1 1 d . . . C2A C 0.31364(17) 0.1854(6) 0.1500(4) 0.0698(12) Uani 1 1 d . . . C3A C 0.3267(3) 0.0215(8) 0.1499(5) 0.0900(16) Uani 1 1 d . . . H3A H 0.2995 -0.057 0.1225 0.108 Uiso 1 1 calc R . . C5A C 0.4208(2) 0.0881(6) 0.2315(4) 0.0781(13) Uani 1 1 d . . . H5A H 0.4569 0.0533 0.2588 0.094 Uiso 1 1 calc R . . C6A C 0.40816(15) 0.2555(6) 0.2318(3) 0.0572(10) Uani 1 1 d . . . C7A C 0.45249(18) 0.3835(6) 0.2732(3) 0.0672(11) Uani 1 1 d . . . H7A1 H 0.4849 0.3278 0.316 0.081 Uiso 1 1 calc R . . H7A2 H 0.4401 0.4617 0.3166 0.081 Uiso 1 1 calc R . . C4A C 0.3804(3) -0.0280(7) 0.1909(5) 0.0914(16) Uani 1 1 d . . . H4A H 0.3895 -0.1403 0.1912 0.11 Uiso 1 1 calc R . . C8A C 0.46790(12) 0.4799(4) 0.1876(2) 0.0445(7) Uani 1 1 d . . . O1 O 0.60413(16) 0.8209(6) 0.3625(3) 0.0984(13) Uani 1 1 d . . . O2 O 0.53070(18) 0.7271(7) 0.3994(3) 0.127(2) Uani 1 1 d . . . H2 H 0.5281 0.6649 0.35 0.191 Uiso 1 1 calc R . . Cl1 Cl 0.57189(12) 1.2236(5) 0.48915(14) 0.238(2) Uani 1 1 d . . . Cl2 Cl 0.6722(3) 1.4577(3) 0.5389(3) 0.316(4) Uani 1 1 d . . . C1 C 0.6356(2) 1.1461(8) 0.5404(3) 0.0820(16) Uani 1 1 d . . . C2 C 0.6832(5) 1.2524(9) 0.5654(5) 0.118(3) Uani 1 1 d . . . C3 C 0.7331(5) 1.178(2) 0.6079(7) 0.157(5) Uani 1 1 d . . . H3 H 0.7651 1.2414 0.6265 0.188 Uiso 1 1 calc R . . C4 C 0.7351(5) 1.005(3) 0.6226(7) 0.200(8) Uani 1 1 d . . . H4 H 0.7693 0.9572 0.6515 0.24 Uiso 1 1 calc R . . C5 C 0.6962(3) 0.9144(9) 0.6011(5) 0.0981(19) Uani 1 1 d . . . H5 H 0.7012 0.8005 0.6126 0.118 Uiso 1 1 calc R . . C6 C 0.6418(2) 0.9794(8) 0.5574(3) 0.0797(14) Uani 1 1 d . . . C8 C 0.5771(2) 0.8039(8) 0.4212(3) 0.0892(17) Uani 1 1 d . . . C7 C 0.5958(3) 0.8592(12) 0.5344(4) 0.132(3) Uani 1 1 d . . . H7A H 0.565 0.9095 0.5522 0.159 Uiso 1 1 calc R . . H7B H 0.6069 0.7615 0.5778 0.159 Uiso 1 1 calc R . . N1B N 0.55376(9) 0.6302(3) 0.07143(19) 0.0356(5) Uani 1 1 d . . . H1B1 H 0.5454 0.5461 0.0255 0.043 Uiso 1 1 calc R . . H1B2 H 0.5365 0.6102 0.12 0.043 Uiso 1 1 calc R . . C1B C 0.62470(17) 0.3812(6) 0.2413(3) 0.0603(9) Uani 1 1 d . . . H1B H 0.6043 0.4377 0.2779 0.072 Uiso 1 1 calc R . . C2B C 0.6454(2) 0.2228(6) 0.2729(3) 0.0774(13) Uani 1 1 d . . . H2B H 0.6383 0.1731 0.3301 0.093 Uiso 1 1 calc R . . C3B C 0.67585(18) 0.1408(6) 0.2203(4) 0.0705(12) Uani 1 1 d . . . H3B H 0.6904 0.0363 0.2425 0.085 Uiso 1 1 calc R . . C4B C 0.68509(16) 0.2117(6) 0.1353(4) 0.0672(11) Uani 1 1 d . . . H4B H 0.7055 0.1541 0.0992 0.081 Uiso 1 1 calc R . . C5B C 0.66477(14) 0.3671(6) 0.1015(3) 0.0577(9) Uani 1 1 d . . . H5B H 0.6713 0.4134 0.0429 0.069 Uiso 1 1 calc R . . C6B C 0.63455(12) 0.4543(4) 0.1553(2) 0.0444(7) Uani 1 1 d . . . C7B C 0.61454(12) 0.6270(5) 0.1224(3) 0.0500(8) Uani 1 1 d . . . H7B1 H 0.6335 0.6694 0.0746 0.06 Uiso 1 1 calc R . . H7B2 H 0.6231 0.6994 0.1824 0.06 Uiso 1 1 calc R . . C8B C 0.53155(12) 0.7877(4) 0.0171(2) 0.0399(6) Uani 1 1 d . . . H8B H 0.5441 0.7963 -0.045 0.048 Uiso 1 1 calc R . . C9B C 0.55132(16) 0.9415(5) 0.0831(3) 0.0550(8) Uani 1 1 d . . . H9B1 H 0.5911 0.9426 0.1058 0.066 Uiso 1 1 calc R . . H9B2 H 0.5383 0.9375 0.144 0.066 Uiso 1 1 calc R . . C10B C 0.53047(19) 1.0996(5) 0.0222(3) 0.0669(11) Uani 1 1 d . . . H10A H 0.5413 1.1953 0.0673 0.08 Uiso 1 1 calc R . . H10B H 0.5474 1.1102 -0.0335 0.08 Uiso 1 1 calc R . . 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 Cl1A 0.0878(8) 0.0739(7) 0.1050(9) 0.0015(7) 0.0367(7) 0.0033(6) Cl2A 0.0528(6) 0.1677(17) 0.1396(13) 0.0187(12) 0.0146(7) -0.0338(9) O2A 0.0644(15) 0.0798(18) 0.0475(13) -0.0149(13) 0.0240(11) -0.0294(14) O1A 0.0625(14) 0.0588(15) 0.0394(12) 0.0015(10) 0.0122(10) -0.0184(12) C1A 0.062(2) 0.063(2) 0.055(2) 0.0052(18) 0.0242(17) -0.0140(18) C2A 0.056(2) 0.086(3) 0.068(2) 0.008(2) 0.0207(18) -0.025(2) C3A 0.103(4) 0.080(4) 0.091(3) 0.002(3) 0.034(3) -0.039(3) C5A 0.102(4) 0.073(3) 0.068(3) 0.024(2) 0.038(3) 0.002(3) C6A 0.0556(19) 0.080(3) 0.0378(16) 0.0148(17) 0.0154(14) -0.0178(19) C7A 0.066(2) 0.088(3) 0.0429(18) 0.0112(19) 0.0078(17) -0.027(2) C4A 0.128(5) 0.060(3) 0.101(4) 0.011(3) 0.056(4) -0.010(3) C8A 0.0363(15) 0.057(2) 0.0395(16) 0.0005(14) 0.0094(12) -0.0080(14) O1 0.104(3) 0.133(3) 0.0630(19) -0.029(2) 0.0307(18) -0.051(2) O2 0.125(3) 0.197(5) 0.078(2) -0.069(3) 0.059(2) -0.092(3) Cl1 0.199(2) 0.437(5) 0.0739(10) 0.0370(17) 0.0329(12) 0.234(3) Cl2 0.755(11) 0.0818(15) 0.172(3) -0.0197(15) 0.234(5) -0.035(3) C1 0.089(3) 0.116(5) 0.0387(19) 0.003(2) 0.0162(19) 0.047(3) C2 0.213(9) 0.089(4) 0.067(3) -0.025(3) 0.064(5) -0.039(5) C3 0.124(8) 0.256(15) 0.087(6) -0.059(8) 0.025(5) -0.044(9) C4 0.110(7) 0.37(2) 0.093(6) -0.025(11) -0.012(5) 0.102(13) C5 0.101(4) 0.100(4) 0.074(3) -0.013(3) -0.004(3) 0.013(4) C6 0.089(3) 0.103(4) 0.045(2) -0.019(2) 0.016(2) -0.011(3) C8 0.097(3) 0.126(5) 0.047(2) -0.023(3) 0.026(2) -0.046(3) C7 0.168(7) 0.179(7) 0.057(3) -0.045(4) 0.043(4) -0.089(6) N1B 0.0286(11) 0.0372(13) 0.0390(12) 0.0002(10) 0.0061(9) -0.0021(9) C1B 0.060(2) 0.070(3) 0.0473(19) 0.0004(18) 0.0090(16) -0.0021(18) C2B 0.100(3) 0.073(3) 0.049(2) 0.017(2) 0.004(2) -0.006(3) C3B 0.073(3) 0.052(2) 0.069(2) 0.002(2) -0.009(2) 0.005(2) C4B 0.0483(19) 0.064(2) 0.084(3) -0.008(2) 0.0099(18) 0.0071(18) C5B 0.0388(17) 0.071(2) 0.062(2) 0.0042(19) 0.0121(15) -0.0001(16) C6B 0.0290(13) 0.0518(18) 0.0449(16) 0.0005(14) -0.0019(11) -0.0028(13) C7B 0.0296(14) 0.0512(19) 0.061(2) 0.0049(16) -0.0013(13) -0.0080(13) C8B 0.0389(15) 0.0383(16) 0.0419(15) -0.0003(12) 0.0104(12) -0.0042(13) C9B 0.057(2) 0.0415(18) 0.059(2) 0.0009(16) 0.0045(16) -0.0045(16) C10B 0.083(3) 0.0373(19) 0.073(3) -0.0016(17) 0.010(2) -0.0086(18) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1A C1A 1.738(5) . ? Cl2A C2A 1.731(5) . ? O2A C8A 1.255(4) . ? O1A C8A 1.233(4) . ? C1A C6A 1.376(6) . ? C1A C2A 1.387(6) . ? C2A C3A 1.356(8) . ? C3A C4A 1.380(8) . ? C3A H3A 0.93 . ? C5A C4A 1.379(8) . ? C5A C6A 1.382(7) . ? C5A H5A 0.93 . ? C6A C7A 1.510(5) . ? C7A C8A 1.530(5) . ? C7A H7A1 0.97 . ? C7A H7A2 0.97 . ? C4A H4A 0.93 . ? O1 C8 1.195(5) . ? O2 C8 1.289(6) . ? O2 H2 0.82 . ? Cl1 C1 1.689(5) . ? Cl2 C2 1.692(8) . ? C1 C6 1.359(8) . ? C1 C2 1.442(10) . ? C2 C3 1.371(16) . ? C3 C4 1.401(19) . ? C3 H3 0.93 . ? C4 C5 1.20(2) . ? C4 H4 0.93 . ? C5 C6 1.439(9) . ? C5 H5 0.93 . ? C6 C7 1.480(8) . ? C8 C7 1.531(6) . ? C7 H7A 0.97 . ? C7 H7B 0.97 . ? N1B C8B 1.489(4) . ? N1B C7B 1.504(4) . ? N1B H1B1 0.9 . ? N1B H1B2 0.9 . ? C1B C6B 1.385(5) . ? C1B C2B 1.395(7) . ? C1B H1B 0.93 . ? C2B C3B 1.361(7) . ? C2B H2B 0.93 . ? C3B C4B 1.360(7) . ? C3B H3B 0.93 . ? C4B C5B 1.376(6) . ? C4B H4B 0.93 . ? C5B C6B 1.387(5) . ? C5B H5B 0.93 . ? C6B C7B 1.499(5) . ? C7B H7B1 0.97 . ? C7B H7B2 0.97 . ? C8B C9B 1.521(5) . ? C8B C8B 1.539(6) 2_655 ? C8B H8B 0.98 . ? C9B C10B 1.523(5) . ? C9B H9B1 0.97 . ? C9B H9B2 0.97 . ? C10B C10B 1.495(9) 2_655 ? C10B H10A 0.97 . ? C10B H10B 0.97 . ? 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 _geom_angle_publ_flag C6A C1A C2A 121.5(4) . . ? C6A C1A Cl1A 119.4(3) . . ? C2A C1A Cl1A 119.1(4) . . ? C3A C2A C1A 120.0(5) . . ? C3A C2A Cl2A 120.2(4) . . ? C1A C2A Cl2A 119.8(4) . . ? C2A C3A C4A 119.5(5) . . ? C2A C3A H3A 120.2 . . ? C4A C3A H3A 120.2 . . ? C4A C5A C6A 120.6(5) . . ? C4A C5A H5A 119.7 . . ? C6A C5A H5A 119.7 . . ? C1A C6A C5A 118.0(4) . . ? C1A C6A C7A 121.2(4) . . ? C5A C6A C7A 120.8(4) . . ? C6A C7A C8A 112.9(3) . . ? C6A C7A H7A1 109 . . ? C8A C7A H7A1 109 . . ? C6A C7A H7A2 109 . . ? C8A C7A H7A2 109 . . ? H7A1 C7A H7A2 107.8 . . ? C5A C4A C3A 120.4(5) . . ? C5A C4A H4A 119.8 . . ? C3A C4A H4A 119.8 . . ? O1A C8A O2A 124.2(3) . . ? O1A C8A C7A 120.2(3) . . ? O2A C8A C7A 115.6(3) . . ? C8 O2 H2 109.5 . . ? C6 C1 C2 119.5(6) . . ? C6 C1 Cl1 118.9(5) . . ? C2 C1 Cl1 121.6(6) . . ? C3 C2 C1 117.3(8) . . ? C3 C2 Cl2 126.1(10) . . ? C1 C2 Cl2 116.6(8) . . ? C2 C3 C4 118.7(10) . . ? C2 C3 H3 120.6 . . ? C4 C3 H3 120.6 . . ? C5 C4 C3 125.1(10) . . ? C5 C4 H4 117.4 . . ? C3 C4 H4 117.4 . . ? C4 C5 C6 120.8(11) . . ? C4 C5 H5 119.6 . . ? C6 C5 H5 119.6 . . ? C1 C6 C5 118.6(6) . . ? C1 C6 C7 123.9(6) . . ? C5 C6 C7 117.5(7) . . ? O1 C8 O2 124.4(4) . . ? O1 C8 C7 123.6(5) . . ? O2 C8 C7 111.8(4) . . ? C6 C7 C8 113.6(5) . . ? C6 C7 H7A 108.8 . . ? C8 C7 H7A 108.8 . . ? C6 C7 H7B 108.8 . . ? C8 C7 H7B 108.8 . . ? H7A C7 H7B 107.7 . . ? C8B N1B C7B 115.9(2) . . ? C8B N1B H1B1 108.3 . . ? C7B N1B H1B1 108.3 . . ? C8B N1B H1B2 108.3 . . ? C7B N1B H1B2 108.3 . . ? H1B1 N1B H1B2 107.4 . . ? C6B C1B C2B 120.0(4) . . ? C6B C1B H1B 120 . . ? C2B C1B H1B 120 . . ? C3B C2B C1B 120.1(4) . . ? C3B C2B H2B 119.9 . . ? C1B C2B H2B 119.9 . . ? C4B C3B C2B 119.9(4) . . ? C4B C3B H3B 120 . . ? C2B C3B H3B 120 . . ? C3B C4B C5B 121.3(4) . . ? C3B C4B H4B 119.4 . . ? C5B C4B H4B 119.3 . . ? C4B C5B C6B 119.7(4) . . ? C4B C5B H5B 120.1 . . ? C6B C5B H5B 120.1 . . ? C1B C6B C5B 118.9(4) . . ? C1B C6B C7B 120.8(3) . . ? C5B C6B C7B 120.2(3) . . ? C6B C7B N1B 111.7(3) . . ? C6B C7B H7B1 109.3 . . ? N1B C7B H7B1 109.3 . . ? C6B C7B H7B2 109.3 . . ? N1B C7B H7B2 109.3 . . ? H7B1 C7B H7B2 107.9 . . ? N1B C8B C9B 112.6(2) . . ? N1B C8B C8B 111.40(18) . 2_655 ? C9B C8B C8B 108.6(2) . 2_655 ? N1B C8B H8B 108.1 . . ? C9B C8B H8B 108.1 . . ? C8B C8B H8B 108.1 2_655 . ? C8B C9B C10B 110.7(3) . . ? C8B C9B H9B1 109.5 . . ? C10B C9B H9B1 109.5 . . ? C8B C9B H9B2 109.5 . . ? C10B C9B H9B2 109.5 . . ? H9B1 C9B H9B2 108.1 . . ? C10B C10B C9B 112.3(3) 2_655 . ? C10B C10B H10A 109.2 2_655 . ? C9B C10B H10A 109.2 . . ? C10B C10B H10B 109.2 2_655 . ? C9B C10B H10B 109.2 . . ? H10A C10B H10B 107.9 . . ? 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C6A C1A C2A C3A -0.6(6) . . . . ? Cl1A C1A C2A C3A 179.5(4) . . . . ? C6A C1A C2A Cl2A -179.3(3) . . . . ? Cl1A C1A C2A Cl2A 0.8(5) . . . . ? C1A C2A C3A C4A 0.4(7) . . . . ? Cl2A C2A C3A C4A 179.1(4) . . . . ? C2A C1A C6A C5A 0.4(5) . . . . ? Cl1A C1A C6A C5A -179.6(3) . . . . ? C2A C1A C6A C7A 178.4(3) . . . . ? Cl1A C1A C6A C7A -1.7(5) . . . . ? C4A C5A C6A C1A -0.2(6) . . . . ? C4A C5A C6A C7A -178.1(4) . . . . ? C1A C6A C7A C8A -74.8(5) . . . . ? C5A C6A C7A C8A 103.1(4) . . . . ? C6A C5A C4A C3A 0.1(7) . . . . ? C2A C3A C4A C5A -0.2(8) . . . . ? C6A C7A C8A O1A -10.0(6) . . . . ? C6A C7A C8A O2A 172.1(4) . . . . ? C6 C1 C2 C3 -1.3(8) . . . . ? Cl1 C1 C2 C3 179.2(5) . . . . ? C6 C1 C2 Cl2 178.4(4) . . . . ? Cl1 C1 C2 Cl2 -1.1(6) . . . . ? C1 C2 C3 C4 1.1(12) . . . . ? Cl2 C2 C3 C4 -178.6(7) . . . . ? C2 C3 C4 C5 0.0(17) . . . . ? C3 C4 C5 C6 -0.8(15) . . . . ? C2 C1 C6 C5 0.5(6) . . . . ? Cl1 C1 C6 C5 180.0(4) . . . . ? C2 C1 C6 C7 -179.9(4) . . . . ? Cl1 C1 C6 C7 -0.4(6) . . . . ? C4 C5 C6 C1 0.6(9) . . . . ? C4 C5 C6 C7 -179.0(7) . . . . ? C1 C6 C7 C8 82.7(8) . . . . ? C5 C6 C7 C8 -97.7(8) . . . . ? O1 C8 C7 C6 17.6(12) . . . . ? O2 C8 C7 C6 -167.0(7) . . . . ? C6B C1B C2B C3B 0.9(6) . . . . ? C1B C2B C3B C4B -1.6(7) . . . . ? C2B C3B C4B C5B 0.9(6) . . . . ? C3B C4B C5B C6B 0.5(6) . . . . ? C2B C1B C6B C5B 0.4(5) . . . . ? C2B C1B C6B C7B -177.6(3) . . . . ? C4B C5B C6B C1B -1.1(5) . . . . ? C4B C5B C6B C7B 177.0(3) . . . . ? C1B C6B C7B N1B -75.0(4) . . . . ? C5B C6B C7B N1B 107.0(3) . . . . ? C8B N1B C7B C6B -168.1(3) . . . . ? C7B N1B C8B C9B -48.8(4) . . . . ? C7B N1B C8B C8B -171.0(3) . . . 2_655 ? N1B C8B C9B C10B 176.5(3) . . . . ? C8B C8B C9B C10B -59.7(4) 2_655 . . . ? C8B C9B C10B C10B 54.6(6) . . . 2_655 ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O2 H2 O2A 0.82 1.81 2.568(4) 153.9 . N1B H1B1 O1A 0.9 1.91 2.738(3) 152.6 2_655 N1B H1B2 O2A 0.9 1.81 2.708(3) 172.1 . # Attachment '- CCDC818798_reviewed_archive.cif' #\#CIF_1.1 # CIF produced by WinGX routine CIF_UPDATE # Created on 2011-06-27 at 15:54:56 # Using CIFtbx version 2.6.2 16 Jun 1998 # Dictionary name : cif_core.dic # Dictionary vers : 2.3 # Request file : c:\program files\wingx\files\archive.dat # CIF files read : th285 struct data_th285 _database_code_depnum_ccdc_archive 'CCDC 818798' #TrackingRef '- CCDC818798_reviewed_archive.cif' _audit_creation_date 2011-06-27T15:54:56-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_conform_dict_name cif_core.dic _audit_conform_dict_version 2.3 _audit_conform_dict_location ftp://ftp.iucr.org/pub/cif_core.dic #----------------------------------------------------------------------------# # CHEMICAL INFORMATION # #----------------------------------------------------------------------------# _chemical_name_systematic ; ? ; _chemical_formula_moiety 'C8 H6 Cl2 O2' _chemical_formula_sum 'C8 H6 Cl2 O2' _chemical_formula_weight 205.03 _chemical_compound_source 'synthesis as described' #----------------------------------------------------------------------------# # UNIT CELL INFORMATION # #----------------------------------------------------------------------------# _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/c' _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 4.8955(5) _cell_length_b 12.3245(12) _cell_length_c 14.5030(14) _cell_angle_alpha 90 _cell_angle_beta 94.270(2) _cell_angle_gamma 90 _cell_volume 872.60(15) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _cell_measurement_wavelength 0.71073 #----------------------------------------------------------------------------# # CRYSTAL INFORMATION # #----------------------------------------------------------------------------# _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.4 _exptl_crystal_size_mid 0.2 _exptl_crystal_size_min 0.1 _exptl_crystal_density_diffrn 1.561 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 416 _exptl_special_details ; ? ; #----------------------------------------------------------------------------# # ABSORPTION CORRECTION # #----------------------------------------------------------------------------# _exptl_absorpt_coefficient_mu 0.695 _exptl_absorpt_correction_type none #----------------------------------------------------------------------------# # DATA COLLECTION # #----------------------------------------------------------------------------# _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_reflns_av_R_equivalents 0.0186 _diffrn_reflns_av_unetI/netI 0.0168 _diffrn_reflns_number 6796 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_theta_min 2.17 _diffrn_reflns_theta_max 26.38 _diffrn_reflns_theta_full 26.38 _diffrn_measured_fraction_theta_full 0.993 _diffrn_measured_fraction_theta_max 0.993 _reflns_number_total 1774 _reflns_number_gt 1523 _reflns_threshold_expression >2sigma(I) #----------------------------------------------------------------------------# # COMPUTER PROGRAMS USED # #----------------------------------------------------------------------------# _computing_structure_solution 'SHELXS-97 (Sheldrick, 1997)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics 'Ortep-3 for Windows (Farrugia, 1997)' _computing_publication_material 'WinGX publication routines (Farrugia, 1999)' #----------------------------------------------------------------------------# # REFINEMENT INFORMATION # #----------------------------------------------------------------------------# _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0754P)^2^+0.3762P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_number_reflns 1774 _refine_ls_number_parameters 110 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0542 _refine_ls_R_factor_gt 0.0477 _refine_ls_wR_factor_ref 0.1362 _refine_ls_wR_factor_gt 0.1307 _refine_ls_goodness_of_fit_ref 1.058 _refine_ls_restrained_S_all 1.058 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0 _refine_diff_density_max 0.408 _refine_diff_density_min -0.275 _refine_diff_density_rms 0.058 #----------------------------------------------------------------------------# # ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS # #----------------------------------------------------------------------------# 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 0 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.05591(18) 0.85895(6) 0.03342(4) 0.0702(3) Uani 1 1 d . . . Cl2 Cl 0.48717(18) 1.01010(6) 0.13967(6) 0.0794(3) Uani 1 1 d . . . O1 O 0.1237(3) 0.57684(15) 0.09354(13) 0.0585(5) Uani 1 1 d . . . O2 O -0.2834(4) 0.58018(16) 0.01767(14) 0.0635(5) Uani 1 1 d . . . H2 H -0.2227 0.5268 -0.0077 0.095 Uiso 1 1 calc R . . C1 C -0.1122(4) 0.61151(18) 0.08193(16) 0.0420(5) Uani 1 1 d . . . C2 C -0.2189(5) 0.6933(2) 0.14776(18) 0.0515(6) Uani 1 1 d . . . H2A H -0.3491 0.7402 0.1135 0.062 Uiso 1 1 calc R . . H2B H -0.3169 0.6549 0.1935 0.062 Uiso 1 1 calc R . . C3 C -0.0021(4) 0.76281(18) 0.19733(15) 0.0405(5) Uani 1 1 d . . . C4 C 0.0660(6) 0.7495(2) 0.29105(17) 0.0554(6) Uani 1 1 d . . . H4 H -0.0211 0.6962 0.3236 0.066 Uiso 1 1 calc R . . C5 C 0.2626(6) 0.8147(2) 0.33688(18) 0.0637(7) Uani 1 1 d . . . H5 H 0.3071 0.8048 0.3998 0.076 Uiso 1 1 calc R . . C6 C 0.3915(6) 0.8937(2) 0.29015(19) 0.0579(7) Uani 1 1 d . . . H6 H 0.5241 0.937 0.3211 0.069 Uiso 1 1 calc R . . C7 C 0.3250(5) 0.90893(19) 0.19740(17) 0.0477(6) Uani 1 1 d . . . C8 C 0.1312(5) 0.84296(17) 0.15100(15) 0.0407(5) 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 Cl1 0.1040(6) 0.0652(5) 0.0404(4) 0.0025(3) -0.0011(3) 0.0049(4) Cl2 0.0877(6) 0.0539(4) 0.1002(7) -0.0024(4) 0.0310(5) -0.0182(4) O1 0.0429(9) 0.0632(11) 0.0670(11) -0.0250(9) -0.0110(8) 0.0126(8) O2 0.0500(10) 0.0619(11) 0.0754(12) -0.0324(10) -0.0171(9) 0.0096(8) C1 0.0387(11) 0.0376(11) 0.0491(12) -0.0086(9) -0.0007(9) -0.0029(9) C2 0.0411(12) 0.0528(14) 0.0610(15) -0.0192(12) 0.0059(10) -0.0024(10) C3 0.0412(11) 0.0384(11) 0.0420(11) -0.0089(9) 0.0043(9) 0.0046(9) C4 0.0701(17) 0.0535(14) 0.0433(13) 0.0002(11) 0.0083(11) 0.0008(12) C5 0.0794(19) 0.0684(17) 0.0418(13) -0.0063(12) -0.0057(12) -0.0012(15) C6 0.0568(15) 0.0561(15) 0.0590(15) -0.0186(12) -0.0079(12) -0.0035(12) C7 0.0502(13) 0.0377(11) 0.0563(14) -0.0094(10) 0.0103(11) 0.0020(10) C8 0.0469(12) 0.0387(11) 0.0368(11) -0.0049(8) 0.0038(9) 0.0094(9) #----------------------------------------------------------------------------# # MOLECULAR GEOMETRY # #----------------------------------------------------------------------------# _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 C8 1.729(2) . ? Cl2 C7 1.728(3) . ? O1 C1 1.231(3) . ? O2 C1 1.266(3) . ? O2 H2 0.82 . ? C1 C2 1.508(3) . ? C2 C3 1.505(3) . ? C2 H2A 0.97 . ? C2 H2B 0.97 . ? C3 C8 1.385(3) . ? C3 C4 1.385(3) . ? C4 C5 1.385(4) . ? C4 H4 0.93 . ? C5 C6 1.367(4) . ? C5 H5 0.93 . ? C6 C7 1.373(4) . ? C6 H6 0.93 . ? C7 C8 1.385(3) . ? 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 _geom_angle_publ_flag C1 O2 H2 109.5 . . ? O1 C1 O2 123.9(2) . . ? O1 C1 C2 120.7(2) . . ? O2 C1 C2 115.36(19) . . ? C3 C2 C1 114.70(19) . . ? C3 C2 H2A 108.6 . . ? C1 C2 H2A 108.6 . . ? C3 C2 H2B 108.6 . . ? C1 C2 H2B 108.6 . . ? H2A C2 H2B 107.6 . . ? C8 C3 C4 118.2(2) . . ? C8 C3 C2 121.0(2) . . ? C4 C3 C2 120.7(2) . . ? C3 C4 C5 120.7(2) . . ? C3 C4 H4 119.7 . . ? C5 C4 H4 119.7 . . ? C6 C5 C4 120.4(2) . . ? C6 C5 H5 119.8 . . ? C4 C5 H5 119.8 . . ? C5 C6 C7 119.9(2) . . ? C5 C6 H6 120.1 . . ? C7 C6 H6 120.1 . . ? C6 C7 C8 120.0(2) . . ? C6 C7 Cl2 119.30(19) . . ? C8 C7 Cl2 120.7(2) . . ? C3 C8 C7 120.9(2) . . ? C3 C8 Cl1 119.08(18) . . ? C7 C8 Cl1 120.02(18) . . ? 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_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag O1 C1 C2 C3 25.9(4) . . . . ? O2 C1 C2 C3 -156.2(2) . . . . ? C1 C2 C3 C8 71.7(3) . . . . ? C1 C2 C3 C4 -109.4(3) . . . . ? C8 C3 C4 C5 -0.1(4) . . . . ? C2 C3 C4 C5 -179.0(2) . . . . ? C3 C4 C5 C6 0.3(4) . . . . ? C4 C5 C6 C7 0.4(4) . . . . ? C5 C6 C7 C8 -1.2(4) . . . . ? C5 C6 C7 Cl2 179.3(2) . . . . ? C4 C3 C8 C7 -0.8(3) . . . . ? C2 C3 C8 C7 178.1(2) . . . . ? C4 C3 C8 Cl1 178.41(18) . . . . ? C2 C3 C8 Cl1 -2.7(3) . . . . ? C6 C7 C8 C3 1.4(3) . . . . ? Cl2 C7 C8 C3 -179.05(17) . . . . ? C6 C7 C8 Cl1 -177.75(19) . . . . ? Cl2 C7 C8 Cl1 1.8(3) . . . . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A O2 H2 O1 0.82 1.87 2.673(2) 165 3_565