# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_2-Me-SP2 _database_code_depnum_ccdc_archive 'CCDC 888277' #TrackingRef '1a.cif' #============================================================================== # CHEMICAL DATA _chemical_formula_sum 'C14 H14 Cl N' _chemical_formula_moiety 'C14 H14 Cl N' _chemical_formula_weight 231.72 _chemical_melting_point ? #============================================================================== # CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/n 1' _symmetry_space_group_name_Hall '-P 2yn' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 +X,+Y,+Z 2 1/2-X,1/2+Y,1/2-Z 3 -X,-Y,-Z 4 1/2+X,1/2-Y,1/2+Z #------------------------------------------------------------------------------ _cell_length_a 4.84119(15) _cell_length_b 31.5272(10) _cell_length_c 7.9505(3) _cell_angle_alpha 90.0000 _cell_angle_beta 93.844(3) _cell_angle_gamma 90.0000 _cell_volume 1210.75(7) _cell_formula_units_Z 4 _cell_measurement_reflns_used 5001 _cell_measurement_theta_min 5.62 _cell_measurement_theta_max 68.08 _cell_measurement_temperature 123 #------------------------------------------------------------------------------ _exptl_crystal_description platelet _exptl_crystal_colour colorless _exptl_crystal_size_max 0.300 _exptl_crystal_size_mid 0.050 _exptl_crystal_size_min 0.020 _exptl_crystal_density_diffrn 1.271 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 488.00 _exptl_absorpt_coefficient_mu 2.538 _exptl_absorpt_correction_type none #============================================================================== # EXPERIMENTAL DATA _diffrn_ambient_temperature 123 _diffrn_radiation_type 'Cu Ka' _diffrn_radiation_wavelength 1.54187 _diffrn_measurement_device_type 'Rigaku R-AXIS RAPID' _diffrn_measurement_method w _diffrn_detector_area_resol_mean 10.000 _diffrn_reflns_number 12168 _diffrn_reflns_av_R_equivalents 0.1540 _diffrn_reflns_theta_max 68.23 _diffrn_reflns_theta_full 68.23 _diffrn_measured_fraction_theta_max 0.979 _diffrn_measured_fraction_theta_full 0.979 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -37 _diffrn_reflns_limit_k_max 37 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_decay_% ? #============================================================================== # REFINEMENT DATA _refine_special_details ; Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F^2^. R-factor (gt) are based on F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 2173 _reflns_number_gt 1290 _reflns_threshold_expression F^2^>2.0s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0929 _refine_ls_wR_factor_ref 0.2658 _refine_ls_number_restraints 0 _refine_ls_hydrogen_treatment constr _refine_ls_number_reflns 2173 _refine_ls_number_parameters 145 _refine_ls_goodness_of_fit_ref 1.040 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[s^2^(Fo^2^)+(0.1363P)^2^+0.1121P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_ls_shift/su_max 0.000 _refine_diff_density_max 0.600 _refine_diff_density_min -0.880 _refine_ls_extinction_method none _refine_ls_extinction_coef ? 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 for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; N N 0.0311 0.0180 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; H H 0.0000 0.0000 ; International Tables for Crystallography (1992, Vol. C, Table 6.1.1.4) ; Cl Cl 0.3639 0.7018 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; #============================================================================== # ATOMIC COORDINATES AND THERMAL PARAMETERS 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 0.4562(3) 0.45977(3) 0.75820(14) 0.0433(5) Uani 1.0 4 d . . . N1 N 1.1471(9) 0.46602(11) 0.2212(5) 0.0402(10) Uani 1.0 4 d . . . C1 C 1.0745(11) 0.45840(12) 0.3792(6) 0.0388(12) Uani 1.0 4 d . . . C2 C 0.8724(9) 0.42960(13) 0.4072(6) 0.0387(11) Uani 1.0 4 d . . . C3 C 0.7397(10) 0.40767(13) 0.2721(6) 0.0377(11) Uani 1.0 4 d . . . C4 C 0.8221(11) 0.41721(14) 0.1101(6) 0.0423(12) Uani 1.0 4 d . . . C5 C 1.0225(11) 0.44677(14) 0.0881(7) 0.0422(12) Uani 1.0 4 d . . . C6 C 0.5264(10) 0.37573(13) 0.2879(6) 0.0400(11) Uani 1.0 4 d . . . C7 C 0.4134(10) 0.36503(13) 0.4313(6) 0.0395(12) Uani 1.0 4 d . . . C8 C 0.2001(10) 0.33241(13) 0.4507(7) 0.0400(12) Uani 1.0 4 d . . . C9 C 0.0909(11) 0.32470(13) 0.6071(7) 0.0432(13) Uani 1.0 4 d . . . C10 C -0.1132(10) 0.29359(14) 0.6160(7) 0.0444(13) Uani 1.0 4 d . . . C11 C -0.2088(11) 0.27020(14) 0.4784(7) 0.0481(13) Uani 1.0 4 d . . . C12 C -0.1013(11) 0.27775(14) 0.3215(7) 0.0471(13) Uani 1.0 4 d . . . C13 C 0.1012(11) 0.30829(14) 0.3103(7) 0.0440(12) Uani 1.0 4 d . . . C14 C 0.1915(12) 0.34826(15) 0.7625(7) 0.0511(14) Uani 1.0 4 d . . . H1 H 1.2807 0.4843 0.2058 0.0483 Uiso 1.0 4 calc R . . H1A H 1.1647 0.4732 0.4715 0.0465 Uiso 1.0 4 calc R . . H2 H 0.8217 0.4244 0.5188 0.0464 Uiso 1.0 4 calc R . . H4 H 0.7374 0.4029 0.0149 0.0508 Uiso 1.0 4 calc R . . H5 H 1.0728 0.4536 -0.0222 0.0506 Uiso 1.0 4 calc R . . H6 H 0.4617 0.3612 0.1882 0.0479 Uiso 1.0 4 calc R . . H7 H 0.4771 0.3800 0.5301 0.0474 Uiso 1.0 4 calc R . . H10 H -0.1887 0.2884 0.7213 0.0533 Uiso 1.0 4 calc R . . H11 H -0.3465 0.2491 0.4893 0.0578 Uiso 1.0 4 calc R . . H12 H -0.1666 0.2621 0.2247 0.0565 Uiso 1.0 4 calc R . . H13 H 0.1760 0.3132 0.2046 0.0528 Uiso 1.0 4 calc R . . H14A H 0.3829 0.3400 0.7948 0.0613 Uiso 1.0 4 calc R . . H14B H 0.0738 0.3414 0.8544 0.0613 Uiso 1.0 4 calc R . . H14C H 0.1839 0.3788 0.7403 0.0613 Uiso 1.0 4 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_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 Cl1 0.0404(8) 0.0442(8) 0.0445(8) -0.0073(5) -0.0028(6) 0.0017(5) N1 0.031(3) 0.037(2) 0.053(3) 0.0002(16) -0.0004(19) 0.0029(18) C1 0.043(3) 0.038(3) 0.034(3) 0.003(2) -0.004(3) -0.0030(19) C2 0.035(3) 0.036(3) 0.045(3) 0.004(2) 0.002(2) 0.0029(19) C3 0.039(3) 0.033(3) 0.041(3) 0.0063(19) -0.003(3) -0.0027(19) C4 0.048(3) 0.042(3) 0.036(3) -0.002(2) -0.008(3) -0.002(2) C5 0.041(3) 0.042(3) 0.043(3) 0.001(3) -0.001(3) 0.005(2) C6 0.039(3) 0.035(3) 0.046(3) -0.001(2) -0.002(3) 0.001(2) C7 0.033(3) 0.034(3) 0.050(3) 0.0004(18) -0.007(3) -0.002(2) C8 0.033(3) 0.033(3) 0.054(3) 0.0019(19) -0.003(3) 0.000(2) C9 0.043(3) 0.035(3) 0.051(3) 0.003(2) -0.001(3) 0.002(2) C10 0.035(3) 0.040(3) 0.059(4) 0.003(2) 0.006(3) 0.009(3) C11 0.039(3) 0.037(3) 0.068(4) -0.004(2) 0.000(3) 0.001(3) C12 0.043(3) 0.038(3) 0.061(4) -0.005(2) 0.004(3) -0.005(3) C13 0.038(3) 0.043(3) 0.052(3) -0.002(2) 0.004(3) -0.004(3) C14 0.052(4) 0.047(3) 0.055(4) -0.004(3) 0.002(3) 0.002(3) #============================================================================== _computing_data_collection 'RAPID AUTO (Rigaku, ????)' _computing_cell_refinement 'RAPID AUTO' _computing_data_reduction 'RAPID AUTO' _computing_structure_solution 'SIR92 (Altomare, et al., 1994)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_publication_material 'CrystalStructure 4.0 (Rigaku, 2010)' _computing_molecular_graphics 'CrystalStructure 4.0' #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 N1 C1 1.349(7) yes . . N1 C5 1.329(6) yes . . C1 C2 1.364(7) yes . . C2 C3 1.397(7) yes . . C3 C4 1.406(7) yes . . C3 C6 1.454(7) yes . . C4 C5 1.365(7) yes . . C6 C7 1.340(7) yes . . C7 C8 1.473(7) yes . . C8 C9 1.405(8) yes . . C8 C13 1.408(7) yes . . C9 C10 1.397(7) yes . . C9 C14 1.495(7) yes . . C10 C11 1.374(7) yes . . C11 C12 1.403(8) yes . . C12 C13 1.381(7) yes . . N1 H1 0.880 no . . C1 H1A 0.950 no . . C2 H2 0.950 no . . C4 H4 0.950 no . . C5 H5 0.950 no . . C6 H6 0.950 no . . C7 H7 0.950 no . . C10 H10 0.950 no . . C11 H11 0.950 no . . C12 H12 0.950 no . . C13 H13 0.950 no . . C14 H14A 0.980 no . . C14 H14B 0.980 no . . C14 H14C 0.980 no . . 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 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 C1 N1 C5 121.9(4) yes . . . N1 C1 C2 120.3(5) yes . . . C1 C2 C3 120.1(5) yes . . . C2 C3 C4 117.0(5) yes . . . C2 C3 C6 124.7(5) yes . . . C4 C3 C6 118.3(4) yes . . . C3 C4 C5 120.8(5) yes . . . N1 C5 C4 119.9(5) yes . . . C3 C6 C7 125.5(5) yes . . . C6 C7 C8 126.4(5) yes . . . C7 C8 C9 121.5(5) yes . . . C7 C8 C13 119.8(5) yes . . . C9 C8 C13 118.7(5) yes . . . C8 C9 C10 118.4(5) yes . . . C8 C9 C14 121.6(5) yes . . . C10 C9 C14 120.0(5) yes . . . C9 C10 C11 122.6(5) yes . . . C10 C11 C12 119.4(5) yes . . . C11 C12 C13 118.9(5) yes . . . C8 C13 C12 122.1(5) yes . . . C1 N1 H1 119.065 no . . . C5 N1 H1 119.067 no . . . N1 C1 H1A 119.839 no . . . C2 C1 H1A 119.836 no . . . C1 C2 H2 119.946 no . . . C3 C2 H2 119.925 no . . . C3 C4 H4 119.620 no . . . C5 C4 H4 119.628 no . . . N1 C5 H5 120.061 no . . . C4 C5 H5 120.073 no . . . C3 C6 H6 117.253 no . . . C7 C6 H6 117.261 no . . . C6 C7 H7 116.782 no . . . C8 C7 H7 116.769 no . . . C9 C10 H10 118.703 no . . . C11 C10 H10 118.711 no . . . C10 C11 H11 120.289 no . . . C12 C11 H11 120.288 no . . . C11 C12 H12 120.564 no . . . C13 C12 H12 120.574 no . . . C8 C13 H13 118.967 no . . . C12 C13 H13 118.977 no . . . C9 C14 H14A 109.465 no . . . C9 C14 H14B 109.465 no . . . C9 C14 H14C 109.476 no . . . H14A C14 H14B 109.470 no . . . H14A C14 H14C 109.476 no . . . H14B C14 H14C 109.476 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 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 C1 N1 C5 C4 -2.5(7) no . . . . C5 N1 C1 C2 1.5(7) no . . . . N1 C1 C2 C3 0.2(7) no . . . . C1 C2 C3 C4 -0.8(6) no . . . . C1 C2 C3 C6 178.6(4) no . . . . C2 C3 C4 C5 -0.2(7) no . . . . C2 C3 C6 C7 5.1(7) no . . . . C4 C3 C6 C7 -175.5(4) no . . . . C6 C3 C4 C5 -179.7(4) no . . . . C3 C4 C5 N1 1.8(7) no . . . . C3 C6 C7 C8 -179.1(4) no . . . . C6 C7 C8 C9 -178.2(4) no . . . . C6 C7 C8 C13 1.6(7) no . . . . C7 C8 C9 C10 179.3(4) no . . . . C7 C8 C9 C14 -1.9(7) no . . . . C7 C8 C13 C12 -179.1(4) no . . . . C9 C8 C13 C12 0.7(7) no . . . . C13 C8 C9 C10 -0.5(7) no . . . . C13 C8 C9 C14 178.3(4) no . . . . C8 C9 C10 C11 0.5(7) no . . . . C14 C9 C10 C11 -178.4(4) no . . . . C9 C10 C11 C12 -0.6(7) no . . . . C10 C11 C12 C13 0.8(7) no . . . . C11 C12 C13 C8 -0.8(7) no . . . . loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_publ_flag _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 N1 C3 2.747(6) no . . C1 C4 2.722(7) no . . C2 C5 2.740(7) no . . C2 C7 3.029(7) no . . C6 C13 2.973(7) no . . C7 C14 2.958(8) no . . C8 C11 2.806(7) no . . C9 C12 2.816(7) no . . C10 C13 2.745(8) no . . Cl1 N1 3.025(4) no . 3_766 Cl1 C1 3.427(5) no . 1_455 Cl1 C4 3.479(5) no . 1_556 Cl1 C5 3.492(6) no . 1_456 N1 Cl1 3.025(4) no . 3_766 N1 C3 3.409(6) no . 1_655 N1 C6 3.410(6) no . 1_655 C1 Cl1 3.427(5) no . 1_655 C1 C1 3.358(6) no . 3_766 C1 C6 3.510(7) no . 1_655 C1 C7 3.382(6) no . 1_655 C2 C7 3.312(6) no . 1_655 C2 C8 3.457(6) no . 1_655 C3 N1 3.409(6) no . 1_455 C3 C8 3.491(7) no . 1_655 C3 C13 3.592(7) no . 1_655 C4 Cl1 3.479(5) no . 1_554 C5 Cl1 3.492(6) no . 1_654 C6 N1 3.410(6) no . 1_455 C6 C1 3.510(7) no . 1_455 C6 C12 3.578(7) no . 1_655 C6 C13 3.497(7) no . 1_655 C7 C1 3.382(6) no . 1_455 C7 C2 3.312(6) no . 1_455 C7 C10 3.469(7) no . 1_655 C7 C11 3.512(7) no . 1_655 C8 C2 3.457(6) no . 1_455 C8 C3 3.491(7) no . 1_455 C8 C11 3.464(7) no . 1_655 C10 C7 3.469(7) no . 1_455 C11 C7 3.512(7) no . 1_455 C11 C8 3.464(7) no . 1_455 C12 C6 3.578(7) no . 1_455 C13 C3 3.592(7) no . 1_455 C13 C6 3.497(7) no . 1_455 N1 H2 3.2088 no . . N1 H4 3.1853 no . . C1 H5 3.1946 no . . C2 H1 3.1408 no . . C2 H4 3.2541 no . . C2 H6 3.3420 no . . C2 H7 2.7049 no . . C3 H1A 3.2516 no . . C3 H5 3.2674 no . . C3 H7 2.6338 no . . C4 H1 3.1221 no . . C4 H2 3.2572 no . . C4 H6 2.5867 no . . C5 H1A 3.1905 no . . C6 H2 2.7241 no . . C6 H4 2.6048 no . . C6 H13 2.6561 no . . C7 H2 2.7778 no . . C7 H13 2.6387 no . . C7 H14A 3.0095 no . . C7 H14C 2.7980 no . . C8 H6 2.6720 no . . C8 H10 3.2617 no . . C8 H12 3.2961 no . . C8 H14A 2.8281 no . . C8 H14B 3.3197 no . . C8 H14C 2.7340 no . . C9 H7 2.6570 no . . C9 H11 3.2832 no . . C9 H13 3.2744 no . . C10 H12 3.2587 no . . C10 H14A 3.0768 no . . C10 H14B 2.5412 no . . C10 H14C 3.1741 no . . C11 H13 3.2538 no . . C12 H10 3.2516 no . . C13 H6 2.6461 no . . C13 H7 3.3235 no . . C13 H11 3.2586 no . . C14 H7 2.5822 no . . C14 H10 2.6412 no . . H1 H1A 2.2496 no . . H1 H5 2.2335 no . . H1A H2 2.3111 no . . H2 H7 2.1857 no . . H4 H5 2.3108 no . . H4 H6 2.3776 no . . H6 H7 2.7783 no . . H6 H13 2.0614 no . . H7 H13 3.5709 no . . H7 H14A 2.5208 no . . H7 H14B 3.5512 no . . H7 H14C 2.2647 no . . H10 H11 2.3094 no . . H10 H14A 3.2285 no . . H10 H14B 2.3129 no . . H10 H14C 3.3711 no . . H11 H12 2.3657 no . . H12 H13 2.3246 no . . Cl1 H1 2.1843 no . 3_766 Cl1 H1A 2.6329 no . 1_455 Cl1 H1A 3.4098 no . 3_766 Cl1 H2 2.9065 no . . Cl1 H4 2.9767 no . 1_556 Cl1 H5 2.6391 no . 1_456 Cl1 H5 3.3617 no . 1_556 Cl1 H7 3.1071 no . . Cl1 H14C 2.8716 no . . N1 H1A 3.5237 no . 3_766 N1 H5 3.1364 no . 3_765 C1 H1A 2.7548 no . 3_766 C1 H7 3.3227 no . 1_655 C2 H1A 3.2223 no . 3_766 C2 H7 3.4048 no . 1_655 C2 H14C 3.3640 no . 1_655 C3 H1 3.2997 no . 1_455 C4 H1 3.4906 no . 1_455 C4 H6 3.5815 no . 1_655 C4 H14B 3.4143 no . 1_654 C5 H1 3.4473 no . 3_765 C5 H5 3.2133 no . 3_765 C5 H6 3.4927 no . 1_655 C7 H2 3.5305 no . 1_455 C8 H2 3.4929 no . 1_455 C8 H11 3.4236 no . 1_655 C9 H2 3.4580 no . 1_455 C9 H7 3.4635 no . 1_455 C9 H12 3.0976 no . 4_555 C10 H7 3.4108 no . 1_455 C10 H11 3.4311 no . 4_555 C10 H12 3.3647 no . 4_455 C10 H12 2.8731 no . 4_555 C10 H14A 3.2521 no . 1_455 C11 H10 3.5149 no . 4_454 C11 H12 3.2200 no . 4_455 C11 H12 3.3279 no . 4_555 C11 H13 3.2544 no . 4_455 C12 H6 3.4968 no . 1_455 C12 H10 3.5736 no . 4_454 C12 H10 3.0313 no . 4_554 C12 H11 3.1067 no . 4_554 C13 H6 3.5932 no . 1_455 C13 H10 3.3056 no . 4_554 C13 H11 3.4853 no . 1_655 C13 H11 3.1525 no . 4_554 C14 H2 3.5022 no . 1_455 C14 H4 3.5240 no . 1_456 C14 H6 3.5685 no . 1_556 C14 H10 3.5780 no . 1_655 C14 H11 3.5704 no . 4_555 C14 H12 3.5634 no . 4_555 H1 Cl1 2.1843 no . 3_766 H1 C3 3.2997 no . 1_655 H1 C4 3.4906 no . 1_655 H1 C5 3.4473 no . 3_765 H1 H5 2.9270 no . 3_765 H1A Cl1 2.6329 no . 1_655 H1A Cl1 3.4098 no . 3_766 H1A N1 3.5237 no . 3_766 H1A C1 2.7548 no . 3_766 H1A C2 3.2223 no . 3_766 H1A H1A 2.3892 no . 3_766 H1A H2 3.5295 no . 1_655 H1A H2 3.2299 no . 3_766 H1A H7 3.3233 no . 1_655 H2 Cl1 2.9065 no . . H2 C7 3.5305 no . 1_655 H2 C8 3.4929 no . 1_655 H2 C9 3.4580 no . 1_655 H2 C14 3.5022 no . 1_655 H2 H1A 3.5295 no . 1_455 H2 H1A 3.2299 no . 3_766 H2 H7 3.4648 no . 1_655 H2 H14C 2.7986 no . 1_655 H4 Cl1 2.9767 no . 1_554 H4 C14 3.5240 no . 1_654 H4 H5 3.5866 no . 1_455 H4 H14A 3.0896 no . 1_554 H4 H14B 2.8837 no . 1_654 H4 H14C 3.4264 no . 1_554 H4 H14C 3.2628 no . 1_654 H5 Cl1 3.3617 no . 1_554 H5 Cl1 2.6391 no . 1_654 H5 N1 3.1364 no . 3_765 H5 C5 3.2133 no . 3_765 H5 H1 2.9270 no . 3_765 H5 H4 3.5866 no . 1_655 H5 H5 3.0368 no . 3_765 H5 H14C 3.0895 no . 1_654 H6 C4 3.5815 no . 1_455 H6 C5 3.4927 no . 1_455 H6 C12 3.4968 no . 1_655 H6 C13 3.5932 no . 1_655 H6 C14 3.5685 no . 1_554 H6 H14A 3.1965 no . 1_554 H6 H14B 3.2076 no . 1_554 H7 Cl1 3.1071 no . . H7 C1 3.3227 no . 1_455 H7 C2 3.4048 no . 1_455 H7 C9 3.4635 no . 1_655 H7 C10 3.4108 no . 1_655 H7 H1A 3.3233 no . 1_455 H7 H2 3.4648 no . 1_455 H7 H10 3.5955 no . 1_655 H10 C11 3.5149 no . 4_555 H10 C12 3.0313 no . 4_455 H10 C12 3.5736 no . 4_555 H10 C13 3.3056 no . 4_455 H10 C14 3.5780 no . 1_455 H10 H7 3.5955 no . 1_455 H10 H11 2.8653 no . 4_555 H10 H12 2.8104 no . 4_455 H10 H12 2.9862 no . 4_555 H10 H13 3.2701 no . 4_455 H10 H14A 2.7289 no . 1_455 H11 C8 3.4236 no . 1_455 H11 C10 3.4311 no . 4_454 H11 C12 3.1067 no . 4_455 H11 C13 3.4853 no . 1_455 H11 C13 3.1525 no . 4_455 H11 C14 3.5704 no . 4_454 H11 H10 2.8653 no . 4_454 H11 H12 2.5336 no . 4_455 H11 H13 2.6021 no . 4_455 H11 H14A 3.4260 no . 4_454 H11 H14B 3.0639 no . 4_454 H12 C9 3.0976 no . 4_454 H12 C10 2.8731 no . 4_454 H12 C10 3.3647 no . 4_554 H12 C11 3.3279 no . 4_454 H12 C11 3.2200 no . 4_554 H12 C14 3.5634 no . 4_454 H12 H10 2.9862 no . 4_454 H12 H10 2.8104 no . 4_554 H12 H11 2.5336 no . 4_554 H12 H13 3.5609 no . 1_455 H12 H14A 3.2718 no . 4_454 H13 C11 3.2544 no . 4_554 H13 H10 3.2701 no . 4_554 H13 H11 2.6021 no . 4_554 H13 H12 3.5609 no . 1_655 H13 H14A 3.5736 no . 1_554 H13 H14B 2.9334 no . 1_554 H14A C10 3.2521 no . 1_655 H14A H4 3.0896 no . 1_556 H14A H6 3.1965 no . 1_556 H14A H10 2.7289 no . 1_655 H14A H11 3.4260 no . 4_555 H14A H12 3.2718 no . 4_555 H14A H13 3.5736 no . 1_556 H14A H14B 3.3470 no . 1_655 H14B C4 3.4143 no . 1_456 H14B H4 2.8837 no . 1_456 H14B H6 3.2076 no . 1_556 H14B H11 3.0639 no . 4_555 H14B H13 2.9334 no . 1_556 H14B H14A 3.3470 no . 1_455 H14C Cl1 2.8716 no . . H14C C2 3.3640 no . 1_455 H14C H2 2.7986 no . 1_455 H14C H4 3.2628 no . 1_456 H14C H4 3.4264 no . 1_556 H14C H5 3.0895 no . 1_456 #============================================================================== loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_D _geom_hbond_site_symmetry_H _geom_hbond_site_symmetry_A _geom_hbond_distance_DA _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_angle_DHA _geom_hbond_publ_flag N1 H1 Cl1 . . 3_766 3.025(4) 0.880 2.184 159.6 no data_3-MESPHCl-2 _database_code_depnum_ccdc_archive 'CCDC 888278' #TrackingRef 'CCDC 888278.cif' #============================================================================== # CHEMICAL DATA _chemical_formula_sum 'C28 H45 Cl3 N2 O4' _chemical_formula_moiety 'C28 H45 Cl3 N2 O4' _chemical_formula_weight 580.03 _chemical_melting_point ? #============================================================================== # CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/n 1' _symmetry_space_group_name_Hall '-P 2yn' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 +X,+Y,+Z 2 1/2-X,1/2+Y,1/2-Z 3 -X,-Y,-Z 4 1/2+X,1/2-Y,1/2+Z #------------------------------------------------------------------------------ _cell_length_a 18.1754(4) _cell_length_b 6.91256(13) _cell_length_c 25.7534(5) _cell_angle_alpha 90.0000 _cell_angle_beta 110.5550(9) _cell_angle_gamma 90.0000 _cell_volume 3029.62(10) _cell_formula_units_Z 4 _cell_measurement_reflns_used 8962 _cell_measurement_theta_min 3.67 _cell_measurement_theta_max 68.22 _cell_measurement_temperature 123 #------------------------------------------------------------------------------ _exptl_crystal_description block _exptl_crystal_colour colorless _exptl_crystal_size_max 0.150 _exptl_crystal_size_mid 0.050 _exptl_crystal_size_min 0.050 _exptl_crystal_density_diffrn 1.272 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1240.00 _exptl_absorpt_coefficient_mu 3.015 _exptl_absorpt_correction_type none #============================================================================== # EXPERIMENTAL DATA _diffrn_ambient_temperature 123 _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54187 _diffrn_measurement_device_type 'Rigaku R-AXIS RAPID' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.000 _diffrn_reflns_number 31413 _diffrn_reflns_av_R_equivalents 0.0608 _diffrn_reflns_theta_max 68.24 _diffrn_reflns_theta_full 68.24 _diffrn_measured_fraction_theta_max 0.969 _diffrn_measured_fraction_theta_full 0.969 _diffrn_reflns_limit_h_min -21 _diffrn_reflns_limit_h_max 21 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_limit_l_max 30 _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_decay_% ? #============================================================================== # REFINEMENT DATA _refine_special_details ; Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F^2^. R-factor (gt) are based on F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 5380 _reflns_number_gt 3377 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0741 _refine_ls_wR_factor_ref 0.2346 _refine_ls_number_restraints 0 _refine_ls_hydrogen_treatment constr _refine_ls_number_reflns 5380 _refine_ls_number_parameters 334 _refine_ls_goodness_of_fit_ref 1.064 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.1340P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_ls_shift/su_max 0.001 _refine_diff_density_max 0.690 _refine_diff_density_min -0.420 _refine_ls_extinction_method none _refine_ls_extinction_coef ? 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 for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; H H 0.0000 0.0000 ; International Tables for Crystallography (1992, Vol. C, Table 6.1.1.4) ; N N 0.0311 0.0180 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; Cl Cl 0.3639 0.7018 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; O O 0.0492 0.0322 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; #============================================================================== # ATOMIC COORDINATES AND THERMAL PARAMETERS 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 0.59193(5) 0.57840(15) 0.95143(4) 0.0574(4) Uani 1.0 4 d . . . Cl2 Cl 0.91569(5) 0.60341(15) 1.07657(4) 0.0566(4) Uani 1.0 4 d . . . Cl3 Cl 0.52873(6) 0.36602(15) 0.76097(5) 0.0644(4) Uani 1.0 4 d . . . O1 O 0.56436(17) 0.2021(5) 0.87916(12) 0.0732(9) Uani 1.0 4 d . . . O2 O 0.49628(17) 0.8610(4) 0.86097(12) 0.0660(8) Uani 1.0 4 d . . . O3 O 0.46301(15) 0.7555(4) 0.76380(12) 0.0642(8) Uani 1.0 4 d . . . O4 O 0.99967(16) 0.4754(4) 0.80032(11) 0.0649(8) Uani 1.0 4 d . . . N1 N 0.84942(18) 0.4321(5) 0.96084(13) 0.0503(8) Uani 1.0 4 d . . . N2 N 0.33507(19) 0.3895(5) 0.92135(14) 0.0541(9) Uani 1.0 4 d . . . C1 C 0.8975(3) 0.3976(6) 0.93256(18) 0.0502(10) Uani 1.0 4 d . . . C2 C 0.8678(3) 0.3809(6) 0.87692(18) 0.0525(10) Uani 1.0 4 d . . . C3 C 0.7870(3) 0.3994(6) 0.84793(16) 0.0532(10) Uani 1.0 4 d . . . C4 C 0.7403(3) 0.4288(6) 0.8797(2) 0.0613(12) Uani 1.0 4 d . . . C5 C 0.7718(3) 0.4461(6) 0.93526(19) 0.0569(11) Uani 1.0 4 d . . . C6 C 0.7478(3) 0.3943(7) 0.7877(3) 0.0702(13) Uani 1.0 4 d . . . C7 C 0.7834(3) 0.3974(7) 0.7525(2) 0.0694(13) Uani 1.0 4 d . . . C8 C 0.7437(3) 0.4017(6) 0.69046(18) 0.0627(12) Uani 1.0 4 d . . . C9 C 0.7917(3) 0.4191(6) 0.65999(19) 0.0672(12) Uani 1.0 4 d . . . C10 C 0.7603(3) 0.4209(7) 0.6029(2) 0.0714(13) Uani 1.0 4 d . . . C11 C 0.6802(4) 0.4076(6) 0.57662(19) 0.0678(13) Uani 1.0 4 d . . . C12 C 0.6290(3) 0.3916(6) 0.6056(2) 0.0631(12) Uani 1.0 4 d . . . C13 C 0.6634(3) 0.3881(6) 0.66418(19) 0.0610(12) Uani 1.0 4 d . . . C14 C 0.5434(3) 0.3803(7) 0.5778(3) 0.0823(15) Uani 1.0 4 d . . . C15 C 0.3899(3) 0.3925(6) 0.89722(18) 0.0564(11) Uani 1.0 4 d . . . C16 C 0.3665(3) 0.3855(6) 0.84106(17) 0.0528(10) Uani 1.0 4 d . . . C17 C 0.2869(3) 0.3762(6) 0.80793(17) 0.0500(10) Uani 1.0 4 d . . . C18 C 0.2332(3) 0.3722(6) 0.83498(18) 0.0514(10) Uani 1.0 4 d . . . C19 C 0.2581(3) 0.3792(6) 0.89122(18) 0.0534(10) Uani 1.0 4 d . . . C20 C 0.2586(3) 0.3724(6) 0.74633(18) 0.0572(11) Uani 1.0 4 d . . . C21 C 0.3036(3) 0.3742(6) 0.71546(19) 0.0607(11) Uani 1.0 4 d . . . C22 C 0.2774(3) 0.3795(6) 0.65448(18) 0.0563(11) Uani 1.0 4 d . . . C23 C 0.3334(3) 0.3820(6) 0.6299(2) 0.0652(12) Uani 1.0 4 d . . . C24 C 0.3115(3) 0.3888(7) 0.5731(2) 0.0702(13) Uani 1.0 4 d . . . C25 C 0.2331(3) 0.3922(7) 0.5405(2) 0.0685(13) Uani 1.0 4 d . . . C26 C 0.1748(3) 0.3900(6) 0.56344(18) 0.0562(11) Uani 1.0 4 d . . . C27 C 0.1977(3) 0.3814(6) 0.62108(19) 0.0582(11) Uani 1.0 4 d . . . C28 C 0.0909(3) 0.3988(7) 0.5287(2) 0.0701(13) Uani 1.0 4 d . . . H1 H 0.8695 0.4460 0.9971 0.0603 Uiso 1.0 4 calc R . . H1A H 0.9525 0.3848 0.9517 0.0603 Uiso 1.0 4 calc R . . H2 H 0.3501 0.3943 0.9577 0.0649 Uiso 1.0 4 calc R . . H2A H 0.9022 0.3564 0.8571 0.0630 Uiso 1.0 4 calc R . . H4 H 0.6850 0.4370 0.8619 0.0736 Uiso 1.0 4 calc R . . H5 H 0.7388 0.4681 0.9562 0.0683 Uiso 1.0 4 calc R . . H6 H 0.6921 0.3882 0.7735 0.0842 Uiso 1.0 4 calc R . . H7 H 0.8392 0.3969 0.7668 0.0833 Uiso 1.0 4 calc R . . H9 H 0.8470 0.4301 0.6783 0.0806 Uiso 1.0 4 calc R . . H10 H 0.7938 0.4313 0.5818 0.0857 Uiso 1.0 4 calc R . . H11 H 0.6592 0.4094 0.5372 0.0813 Uiso 1.0 4 calc R . . H13 H 0.6306 0.3761 0.6857 0.0732 Uiso 1.0 4 calc R . . H14A H 0.5309 0.3623 0.5379 0.0988 Uiso 1.0 4 calc R . . H14B H 0.5192 0.5003 0.5843 0.0988 Uiso 1.0 4 calc R . . H14C H 0.5229 0.2707 0.5927 0.0988 Uiso 1.0 4 calc R . . H15 H 0.4441 0.3994 0.9192 0.0677 Uiso 1.0 4 calc R . . H16 H 0.4050 0.3870 0.8239 0.0634 Uiso 1.0 4 calc R . . H18 H 0.1785 0.3646 0.8141 0.0617 Uiso 1.0 4 calc R . . H19 H 0.2208 0.3768 0.9094 0.0640 Uiso 1.0 4 calc R . . H20 H 0.2034 0.3684 0.7274 0.0686 Uiso 1.0 4 calc R . . H21 H 0.3587 0.3718 0.7348 0.0728 Uiso 1.0 4 calc R . . H23 H 0.3876 0.3790 0.6523 0.0783 Uiso 1.0 4 calc R . . H24 H 0.3505 0.3911 0.5564 0.0842 Uiso 1.0 4 calc R . . H25 H 0.2187 0.3962 0.5013 0.0822 Uiso 1.0 4 calc R . . H27 H 0.1589 0.3767 0.6379 0.0698 Uiso 1.0 4 calc R . . H28A H 0.0590 0.3974 0.5525 0.0841 Uiso 1.0 4 calc R . . H28B H 0.0774 0.2868 0.5038 0.0841 Uiso 1.0 4 calc R . . H28C H 0.0806 0.5180 0.5067 0.0841 Uiso 1.0 4 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_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 Cl1 0.0533(6) 0.0732(7) 0.0457(6) 0.0010(5) 0.0173(5) -0.0021(5) Cl2 0.0481(6) 0.0765(7) 0.0465(7) 0.0004(5) 0.0184(5) -0.0045(5) Cl3 0.0611(7) 0.0708(8) 0.0585(7) 0.0013(5) 0.0175(6) -0.0040(5) O1 0.080(2) 0.071(2) 0.071(2) -0.0049(15) 0.0300(17) -0.0043(17) O2 0.073(2) 0.072(2) 0.0562(19) -0.0008(14) 0.0262(16) 0.0009(15) O3 0.0561(16) 0.071(2) 0.0613(18) -0.0025(13) 0.0153(14) 0.0003(15) O4 0.0737(19) 0.0665(19) 0.0527(18) -0.0013(14) 0.0198(15) 0.0008(15) N1 0.0519(19) 0.059(2) 0.0372(19) -0.0015(15) 0.0128(15) -0.0039(15) N2 0.058(2) 0.062(2) 0.042(2) -0.0008(15) 0.0177(16) -0.0037(15) C1 0.045(2) 0.052(3) 0.055(3) 0.0004(16) 0.020(2) 0.0018(19) C2 0.067(3) 0.050(3) 0.048(3) -0.0015(18) 0.030(3) -0.0012(18) C3 0.069(3) 0.050(3) 0.035(3) -0.0050(18) 0.009(2) 0.0024(17) C4 0.045(3) 0.070(3) 0.062(3) -0.0048(19) 0.010(2) 0.001(3) C5 0.049(3) 0.066(3) 0.058(3) -0.0005(19) 0.020(2) -0.003(3) C6 0.075(3) 0.060(3) 0.077(4) -0.008(3) 0.028(3) 0.000(3) C7 0.076(4) 0.059(3) 0.075(4) -0.004(3) 0.029(3) 0.002(3) C8 0.085(4) 0.053(3) 0.043(3) -0.008(2) 0.014(3) -0.0039(19) C9 0.079(4) 0.068(3) 0.051(3) -0.004(3) 0.019(3) 0.002(3) C10 0.088(4) 0.070(3) 0.055(3) -0.001(3) 0.022(3) 0.008(3) C11 0.104(4) 0.055(3) 0.038(3) 0.001(3) 0.018(3) 0.0008(19) C12 0.075(3) 0.040(3) 0.068(4) -0.0013(19) 0.017(3) 0.001(2) C13 0.090(4) 0.047(3) 0.049(3) -0.004(2) 0.028(3) 0.0015(19) C14 0.089(4) 0.061(3) 0.084(4) -0.003(3) 0.014(3) 0.006(3) C15 0.045(3) 0.069(3) 0.055(3) -0.0005(18) 0.019(2) -0.000(2) C16 0.051(3) 0.066(3) 0.045(3) -0.0012(18) 0.0210(19) 0.0027(19) C17 0.051(3) 0.049(3) 0.046(3) 0.0031(16) 0.0132(19) 0.0040(18) C18 0.043(2) 0.058(3) 0.053(3) -0.0018(16) 0.0170(19) -0.002(2) C19 0.049(3) 0.055(3) 0.062(3) 0.0011(17) 0.027(2) -0.003(2) C20 0.052(3) 0.064(3) 0.052(3) 0.0022(18) 0.012(2) 0.000(2) C21 0.058(3) 0.064(3) 0.059(3) -0.0009(19) 0.019(3) -0.001(2) C22 0.058(3) 0.055(3) 0.050(3) -0.0005(18) 0.012(2) -0.0010(19) C23 0.063(3) 0.068(3) 0.065(4) -0.000(2) 0.023(3) 0.000(3) C24 0.073(3) 0.080(4) 0.060(4) 0.008(3) 0.027(3) 0.006(3) C25 0.087(4) 0.071(3) 0.056(3) 0.009(3) 0.036(3) 0.005(3) C26 0.067(3) 0.050(3) 0.049(3) -0.0011(18) 0.018(3) -0.0000(19) C27 0.069(3) 0.050(3) 0.063(3) 0.0008(19) 0.033(3) -0.000(2) C28 0.078(4) 0.073(3) 0.058(3) -0.004(3) 0.022(3) 0.001(3) #============================================================================== _computing_data_collection 'RAPID AUTO (Rigaku, ????)' _computing_cell_refinement 'RAPID AUTO' _computing_data_reduction 'RAPID AUTO' _computing_structure_solution 'SIR92 (Altomare, et al., 1994)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_publication_material 'CrystalStructure 4.0 (Rigaku, 2010)' _computing_molecular_graphics 'CrystalStructure 4.0' #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 N1 C1 1.341(7) yes . . N1 C5 1.334(5) yes . . N2 C15 1.347(7) yes . . N2 C19 1.342(5) yes . . C1 C2 1.347(6) yes . . C2 C3 1.400(6) yes . . C3 C4 1.385(8) yes . . C3 C6 1.463(7) yes . . C4 C5 1.347(7) yes . . C6 C7 1.286(9) yes . . C7 C8 1.504(7) yes . . C8 C9 1.369(9) yes . . C8 C13 1.380(7) yes . . C9 C10 1.378(7) yes . . C10 C11 1.377(8) yes . . C11 C12 1.387(9) yes . . C12 C13 1.416(7) yes . . C12 C14 1.469(7) yes . . C15 C16 1.358(6) yes . . C16 C17 1.399(5) yes . . C17 C18 1.386(7) yes . . C17 C20 1.486(6) yes . . C18 C19 1.358(7) yes . . C20 C21 1.325(8) yes . . C21 C22 1.473(7) yes . . C22 C23 1.374(8) yes . . C22 C27 1.401(6) yes . . C23 C24 1.376(8) yes . . C24 C25 1.377(7) yes . . C25 C26 1.384(9) yes . . C26 C27 1.395(7) yes . . C26 C28 1.473(6) yes . . N1 H1 0.880 no . . N2 H2 0.880 no . . C1 H1A 0.950 no . . C2 H2A 0.950 no . . C4 H4 0.950 no . . C5 H5 0.950 no . . C6 H6 0.950 no . . C7 H7 0.950 no . . C9 H9 0.950 no . . C10 H10 0.950 no . . C11 H11 0.950 no . . C13 H13 0.950 no . . C14 H14A 0.980 no . . C14 H14B 0.980 no . . C14 H14C 0.980 no . . C15 H15 0.950 no . . C16 H16 0.950 no . . C18 H18 0.950 no . . C19 H19 0.950 no . . C20 H20 0.950 no . . C21 H21 0.950 no . . C23 H23 0.950 no . . C24 H24 0.950 no . . C25 H25 0.950 no . . C27 H27 0.950 no . . C28 H28A 0.980 no . . C28 H28B 0.980 no . . C28 H28C 0.980 no . . 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 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 C1 N1 C5 121.5(4) yes . . . C15 N2 C19 121.6(4) yes . . . N1 C1 C2 119.9(4) yes . . . C1 C2 C3 120.8(5) yes . . . C2 C3 C4 116.3(4) yes . . . C2 C3 C6 126.3(5) yes . . . C4 C3 C6 117.3(4) yes . . . C3 C4 C5 121.4(4) yes . . . N1 C5 C4 120.0(5) yes . . . C3 C6 C7 124.7(5) yes . . . C6 C7 C8 125.2(5) yes . . . C7 C8 C9 116.5(5) yes . . . C7 C8 C13 123.4(6) yes . . . C9 C8 C13 120.2(5) yes . . . C8 C9 C10 120.3(5) yes . . . C9 C10 C11 119.6(6) yes . . . C10 C11 C12 122.3(5) yes . . . C11 C12 C13 116.5(5) yes . . . C11 C12 C14 122.6(5) yes . . . C13 C12 C14 120.9(6) yes . . . C8 C13 C12 121.1(6) yes . . . N2 C15 C16 119.1(4) yes . . . C15 C16 C17 121.4(5) yes . . . C16 C17 C18 117.1(4) yes . . . C16 C17 C20 123.3(5) yes . . . C18 C17 C20 119.7(4) yes . . . C17 C18 C19 120.3(4) yes . . . N2 C19 C18 120.6(5) yes . . . C17 C20 C21 125.8(4) yes . . . C20 C21 C22 127.1(4) yes . . . C21 C22 C23 118.5(4) yes . . . C21 C22 C27 122.1(5) yes . . . C23 C22 C27 119.4(5) yes . . . C22 C23 C24 120.4(5) yes . . . C23 C24 C25 120.0(6) yes . . . C24 C25 C26 121.6(5) yes . . . C25 C26 C27 117.9(4) yes . . . C25 C26 C28 121.6(5) yes . . . C27 C26 C28 120.5(5) yes . . . C22 C27 C26 120.8(5) yes . . . C1 N1 H1 119.262 no . . . C5 N1 H1 119.254 no . . . C15 N2 H2 119.217 no . . . C19 N2 H2 119.227 no . . . N1 C1 H1A 120.029 no . . . C2 C1 H1A 120.042 no . . . C1 C2 H2A 119.574 no . . . C3 C2 H2A 119.579 no . . . C3 C4 H4 119.302 no . . . C5 C4 H4 119.305 no . . . N1 C5 H5 120.024 no . . . C4 C5 H5 120.026 no . . . C3 C6 H6 117.671 no . . . C7 C6 H6 117.637 no . . . C6 C7 H7 117.390 no . . . C8 C7 H7 117.402 no . . . C8 C9 H9 119.868 no . . . C10 C9 H9 119.876 no . . . C9 C10 H10 120.196 no . . . C11 C10 H10 120.189 no . . . C10 C11 H11 118.834 no . . . C12 C11 H11 118.823 no . . . C8 C13 H13 119.448 no . . . C12 C13 H13 119.448 no . . . C12 C14 H14A 109.470 no . . . C12 C14 H14B 109.474 no . . . C12 C14 H14C 109.466 no . . . H14A C14 H14B 109.472 no . . . H14A C14 H14C 109.480 no . . . H14B C14 H14C 109.466 no . . . N2 C15 H15 120.474 no . . . C16 C15 H15 120.457 no . . . C15 C16 H16 119.305 no . . . C17 C16 H16 119.303 no . . . C17 C18 H18 119.867 no . . . C19 C18 H18 119.836 no . . . N2 C19 H19 119.695 no . . . C18 C19 H19 119.694 no . . . C17 C20 H20 117.108 no . . . C21 C20 H20 117.130 no . . . C20 C21 H21 116.437 no . . . C22 C21 H21 116.433 no . . . C22 C23 H23 119.815 no . . . C24 C23 H23 119.812 no . . . C23 C24 H24 120.002 no . . . C25 C24 H24 119.989 no . . . C24 C25 H25 119.227 no . . . C26 C25 H25 119.219 no . . . C22 C27 H27 119.589 no . . . C26 C27 H27 119.590 no . . . C26 C28 H28A 109.465 no . . . C26 C28 H28B 109.471 no . . . C26 C28 H28C 109.467 no . . . H28A C28 H28B 109.467 no . . . H28A C28 H28C 109.472 no . . . H28B C28 H28C 109.485 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 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 C1 N1 C5 C4 -1.2(6) no . . . . C5 N1 C1 C2 1.7(6) no . . . . C15 N2 C19 C18 -0.3(6) no . . . . C19 N2 C15 C16 0.2(6) no . . . . N1 C1 C2 C3 0.0(6) no . . . . C1 C2 C3 C4 -2.0(6) no . . . . C1 C2 C3 C6 176.7(4) no . . . . C2 C3 C4 C5 2.5(6) no . . . . C2 C3 C6 C7 -9.7(7) no . . . . C4 C3 C6 C7 169.1(4) no . . . . C6 C3 C4 C5 -176.4(4) no . . . . C3 C4 C5 N1 -0.9(6) no . . . . C3 C6 C7 C8 -176.9(4) no . . . . C6 C7 C8 C9 175.3(4) no . . . . C6 C7 C8 C13 -5.1(7) no . . . . C7 C8 C9 C10 178.9(4) no . . . . C7 C8 C13 C12 -179.6(4) no . . . . C9 C8 C13 C12 0.1(6) no . . . . C13 C8 C9 C10 -0.8(6) no . . . . C8 C9 C10 C11 0.9(7) no . . . . C9 C10 C11 C12 -0.2(7) no . . . . C10 C11 C12 C13 -0.5(6) no . . . . C10 C11 C12 C14 179.1(4) no . . . . C11 C12 C13 C8 0.5(6) no . . . . C14 C12 C13 C8 -179.0(4) no . . . . N2 C15 C16 C17 0.3(6) no . . . . C15 C16 C17 C18 -0.7(6) no . . . . C15 C16 C17 C20 178.7(4) no . . . . C16 C17 C18 C19 0.6(6) no . . . . C16 C17 C20 C21 1.1(6) no . . . . C18 C17 C20 C21 -179.5(4) no . . . . C20 C17 C18 C19 -178.8(3) no . . . . C17 C18 C19 N2 -0.2(6) no . . . . C17 C20 C21 C22 -177.0(4) no . . . . C20 C21 C22 C23 179.6(4) no . . . . C20 C21 C22 C27 -0.7(7) no . . . . C21 C22 C23 C24 -179.4(4) no . . . . C21 C22 C27 C26 178.8(4) no . . . . C23 C22 C27 C26 -1.4(6) no . . . . C27 C22 C23 C24 0.8(6) no . . . . C22 C23 C24 C25 -0.3(7) no . . . . C23 C24 C25 C26 0.3(7) no . . . . C24 C25 C26 C27 -0.9(6) no . . . . C24 C25 C26 C28 178.4(4) no . . . . C25 C26 C27 C22 1.4(6) no . . . . C28 C26 C27 C22 -177.9(4) no . . . . loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_publ_flag _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 N1 C3 2.734(5) no . . N2 C17 2.741(6) no . . C1 C4 2.707(6) no . . C2 C5 2.710(8) no . . C2 C7 3.031(7) no . . C6 C13 3.007(7) no . . C8 C11 2.748(7) no . . C9 C12 2.800(7) no . . C10 C13 2.757(9) no . . C15 C18 2.738(5) no . . C16 C19 2.709(7) no . . C16 C21 3.030(7) no . . C20 C27 3.021(7) no . . C22 C25 2.760(7) no . . C23 C26 2.790(6) no . . C24 C27 2.757(9) no . . Cl1 O1 3.135(4) no . . Cl1 O2 3.070(3) no . . Cl1 N2 3.081(4) no . 3_667 Cl1 C5 3.558(5) no . . Cl1 C15 3.673(4) no . . Cl2 O4 3.048(3) no . 3_767 Cl2 N1 3.036(4) no . . Cl2 C1 3.485(5) no . 3_767 Cl2 C2 3.690(5) no . 3_767 Cl2 C19 3.539(5) no . 3_667 Cl3 O1 3.096(4) no . . Cl3 O3 2.956(3) no . . Cl3 O4 3.078(3) no . 2_646 O1 Cl1 3.135(4) no . . O1 Cl3 3.096(4) no . . O1 O2 2.627(5) no . 1_545 O1 C4 3.558(6) no . . O1 C9 3.679(7) no . 2_646 O1 C10 3.621(7) no . 2_646 O1 C15 3.611(6) no . . O1 C16 3.609(5) no . . O2 Cl1 3.070(3) no . . O2 O1 2.627(5) no . 1_565 O2 O3 2.469(5) no . . O3 Cl3 2.956(3) no . . O3 O2 2.469(5) no . . O3 O4 2.507(5) no . 2_656 O3 C18 3.670(5) no . 2_556 O4 Cl2 3.048(3) no . 3_767 O4 Cl3 3.078(3) no . 2_656 O4 O3 2.507(5) no . 2_646 O4 C2 3.658(7) no . . N1 Cl2 3.036(4) no . . N1 C11 3.414(5) no . 2_656 N1 C12 3.693(6) no . 2_656 N2 Cl1 3.081(4) no . 3_667 N2 C26 3.486(5) no . 2_546 N2 C26 3.494(5) no . 2_556 N2 C27 3.664(5) no . 2_546 N2 C27 3.557(5) no . 2_556 C1 Cl2 3.485(5) no . 3_767 C1 C11 3.645(6) no . 2_646 C1 C12 3.619(6) no . 2_646 C1 C12 3.539(6) no . 2_656 C1 C14 3.544(7) no . 2_656 C2 Cl2 3.690(5) no . 3_767 C2 O4 3.658(7) no . . C2 C11 3.692(7) no . 2_646 C2 C12 3.410(6) no . 2_646 C2 C12 3.556(6) no . 2_656 C2 C13 3.554(6) no . 2_646 C2 C13 3.648(6) no . 2_656 C3 C8 3.569(6) no . 2_646 C3 C8 3.600(6) no . 2_656 C3 C9 3.593(6) no . 2_646 C3 C13 3.688(6) no . 2_646 C3 C13 3.538(6) no . 2_656 C4 O1 3.558(6) no . . C4 C9 3.658(6) no . 2_646 C4 C9 3.529(6) no . 2_656 C4 C10 3.540(6) no . 2_646 C4 C10 3.432(6) no . 2_656 C4 C11 3.628(6) no . 2_656 C5 Cl1 3.558(5) no . . C5 C10 3.417(6) no . 2_656 C5 C11 3.349(6) no . 2_656 C6 C7 3.574(7) no . 2_646 C6 C7 3.616(7) no . 2_656 C6 C8 3.446(6) no . 2_646 C6 C8 3.547(6) no . 2_656 C7 C6 3.616(7) no . 2_646 C7 C6 3.574(7) no . 2_656 C7 C7 3.651(7) no . 2_646 C7 C7 3.651(7) no . 2_656 C8 C3 3.599(6) no . 2_646 C8 C3 3.569(6) no . 2_656 C8 C6 3.547(6) no . 2_646 C8 C6 3.446(6) no . 2_656 C9 O1 3.679(7) no . 2_656 C9 C3 3.593(6) no . 2_656 C9 C4 3.529(6) no . 2_646 C9 C4 3.658(6) no . 2_656 C10 O1 3.621(7) no . 2_656 C10 C4 3.432(6) no . 2_646 C10 C4 3.540(6) no . 2_656 C10 C5 3.417(6) no . 2_646 C11 N1 3.414(5) no . 2_646 C11 C1 3.645(6) no . 2_656 C11 C2 3.692(7) no . 2_656 C11 C4 3.628(6) no . 2_646 C11 C5 3.349(6) no . 2_646 C12 N1 3.693(6) no . 2_646 C12 C1 3.539(6) no . 2_646 C12 C1 3.619(6) no . 2_656 C12 C2 3.556(6) no . 2_646 C12 C2 3.410(6) no . 2_656 C13 C2 3.648(6) no . 2_646 C13 C2 3.554(6) no . 2_656 C13 C3 3.538(6) no . 2_646 C13 C3 3.688(6) no . 2_656 C14 C1 3.544(7) no . 2_646 C15 Cl1 3.673(4) no . . C15 O1 3.611(6) no . . C15 C27 3.695(6) no . 2_556 C16 O1 3.609(5) no . . C17 C20 3.687(6) no . 2_556 C18 O3 3.670(5) no . 2_546 C18 C21 3.657(6) no . 2_546 C18 C21 3.683(6) no . 2_556 C18 C22 3.428(6) no . 2_546 C18 C22 3.527(6) no . 2_556 C18 C27 3.657(6) no . 2_546 C19 Cl2 3.539(5) no . 3_667 C19 C22 3.633(6) no . 2_546 C19 C22 3.637(6) no . 2_556 C19 C26 3.645(6) no . 2_546 C19 C27 3.573(6) no . 2_546 C19 C27 3.602(6) no . 2_556 C20 C17 3.687(6) no . 2_546 C20 C20 3.481(6) no . 2_546 C20 C20 3.481(6) no . 2_556 C21 C18 3.683(6) no . 2_546 C21 C18 3.657(6) no . 2_556 C22 C18 3.527(6) no . 2_546 C22 C18 3.428(6) no . 2_556 C22 C19 3.637(6) no . 2_546 C22 C19 3.633(6) no . 2_556 C26 N2 3.494(5) no . 2_546 C26 N2 3.486(5) no . 2_556 C26 C19 3.645(6) no . 2_556 C27 N2 3.557(5) no . 2_546 C27 N2 3.664(5) no . 2_556 C27 C15 3.695(6) no . 2_546 C27 C18 3.657(6) no . 2_556 C27 C19 3.602(6) no . 2_546 C27 C19 3.573(6) no . 2_556 C28 C28 3.410(7) no . 3_566 N1 H2A 3.1827 no . . N1 H4 3.1744 no . . N2 H16 3.1868 no . . N2 H18 3.1991 no . . C1 H5 3.1883 no . . C2 H1 3.1169 no . . C2 H4 3.2320 no . . C2 H6 3.3651 no . . C2 H7 2.7013 no . . C3 H1A 3.2486 no . . C3 H5 3.2387 no . . C3 H7 2.5815 no . . C4 H1 3.1112 no . . C4 H2A 3.2313 no . . C4 H6 2.5766 no . . C5 H1A 3.1873 no . . C6 H2A 2.7592 no . . C6 H4 2.5659 no . . C6 H13 2.7417 no . . C7 H2A 2.8136 no . . C7 H9 2.5660 no . . C7 H13 2.7081 no . . C8 H6 2.6231 no . . C8 H10 3.2395 no . . C9 H7 2.5810 no . . C9 H11 3.2330 no . . C9 H13 3.2355 no . . C11 H9 3.2391 no . . C11 H13 3.2460 no . . C11 H14A 2.5604 no . . C11 H14B 3.0685 no . . C11 H14C 3.1738 no . . C12 H10 3.2727 no . . C13 H6 2.6786 no . . C13 H7 3.3566 no . . C13 H9 3.2398 no . . C13 H11 3.2467 no . . C13 H14A 3.3028 no . . C13 H14B 2.8132 no . . C13 H14C 2.6951 no . . C14 H11 2.6666 no . . C14 H13 2.6732 no . . C15 H19 3.1978 no . . C16 H2 3.1231 no . . C16 H18 3.2419 no . . C16 H20 3.3583 no . . C16 H21 2.6922 no . . C17 H15 3.2629 no . . C17 H19 3.2368 no . . C17 H21 2.6414 no . . C18 H2 3.1331 no . . C18 H16 3.2366 no . . C18 H20 2.6294 no . . C19 H15 3.2020 no . . C20 H16 2.7111 no . . C20 H18 2.6362 no . . C20 H27 2.7443 no . . C21 H16 2.7552 no . . C21 H23 2.5923 no . . C21 H27 2.6869 no . . C22 H20 2.6684 no . . C22 H24 3.2429 no . . C23 H21 2.5763 no . . C23 H25 3.2374 no . . C23 H27 3.2506 no . . C25 H23 3.2412 no . . C25 H27 3.2411 no . . C25 H28A 3.2862 no . . C25 H28B 2.7493 no . . C25 H28C 2.7399 no . . C26 H24 3.2629 no . . C27 H20 2.7058 no . . C27 H21 3.3352 no . . C27 H23 3.2560 no . . C27 H25 3.2407 no . . C27 H28A 2.5230 no . . C27 H28B 3.1139 no . . C27 H28C 3.1142 no . . C28 H25 2.6549 no . . C28 H27 2.6493 no . . H1 H1A 2.2475 no . . H1 H5 2.2404 no . . H1A H2A 2.2916 no . . H2 H15 2.2585 no . . H2 H19 2.2425 no . . H2A H7 2.2208 no . . H4 H5 2.2871 no . . H4 H6 2.3491 no . . H6 H7 2.7421 no . . H6 H13 2.1432 no . . H7 H9 2.3427 no . . H9 H10 2.3294 no . . H10 H11 2.3124 no . . H11 H14A 2.3609 no . . H11 H14B 3.2409 no . . H11 H14C 3.4040 no . . H13 H14A 3.5983 no . . H13 H14B 2.8191 no . . H13 H14C 2.6093 no . . H15 H16 2.3041 no . . H16 H21 2.1519 no . . H18 H19 2.3012 no . . H18 H20 2.4279 no . . H20 H21 2.7628 no . . H20 H27 2.1597 no . . H21 H23 2.3602 no . . H23 H24 2.3234 no . . H24 H25 2.3160 no . . H25 H28A 3.5854 no . . H25 H28B 2.7009 no . . H25 H28C 2.6985 no . . H27 H28A 2.3134 no . . H27 H28B 3.3036 no . . H27 H28C 3.3191 no . . Cl1 H2 2.2107 no . 3_667 Cl1 H4 3.4442 no . . Cl1 H5 2.7368 no . . Cl1 H10 3.4990 no . 2_656 Cl1 H15 2.8057 no . . Cl1 H15 3.6179 no . 3_667 Cl1 H28A 3.4933 no . 2_556 Cl1 H28B 2.9174 no . 4_555 Cl1 H28C 3.1716 no . 4_565 Cl2 H1 2.2073 no . . Cl2 H1A 2.7404 no . 3_767 Cl2 H2A 3.1598 no . 3_767 Cl2 H11 3.4809 no . 2_656 Cl2 H14B 3.2899 no . 4_565 Cl2 H14C 3.1763 no . 4_555 Cl2 H19 2.6337 no . 3_667 Cl2 H24 3.5956 no . 4_555 Cl2 H24 3.6673 no . 4_565 Cl3 H4 3.1433 no . . Cl3 H6 2.8748 no . . Cl3 H13 3.1156 no . . Cl3 H16 3.2034 no . . Cl3 H21 2.9225 no . . Cl3 H23 3.0630 no . . O1 H4 2.8847 no . . O1 H5 3.5992 no . . O1 H9 3.1615 no . 2_646 O1 H10 3.0567 no . 2_646 O1 H15 3.0466 no . . O1 H16 3.0252 no . . O1 H25 3.4681 no . 4_555 O1 H28B 3.1357 no . 4_555 O1 H28C 3.5372 no . 4_555 O2 H9 3.3748 no . 2_656 O2 H10 3.6083 no . 2_656 O2 H16 3.6456 no . . O2 H20 3.5428 no . 2_556 O2 H27 2.8322 no . 2_556 O2 H28A 2.7595 no . 2_556 O2 H28C 3.6188 no . 4_565 O3 H9 3.4631 no . 2_656 O3 H16 3.3379 no . . O3 H18 2.7548 no . 2_556 O3 H20 3.2070 no . 2_556 O3 H21 3.1923 no . . O4 H2A 2.7886 no . . O4 H7 2.7883 no . . O4 H9 3.3992 no . . O4 H14C 3.5656 no . 2_656 O4 H18 3.2359 no . 1_655 O4 H23 3.4231 no . 2_656 N1 H11 3.6179 no . 2_646 N1 H11 3.3041 no . 2_656 N1 H14A 3.6775 no . 2_656 N1 H24 3.3182 no . 4_555 N1 H25 3.6899 no . 4_555 N2 H28B 3.4113 no . 2_556 N2 H28C 3.2221 no . 2_546 C1 H1A 3.5877 no . 3_767 C1 H11 3.6903 no . 2_646 C1 H14A 3.4493 no . 2_656 C1 H14A 3.4417 no . 4_555 C1 H14B 3.2374 no . 2_646 C1 H14C 3.1351 no . 2_656 C2 H14B 3.2702 no . 2_646 C2 H14C 3.2742 no . 2_656 C4 H10 3.6919 no . 2_646 C5 H10 3.5349 no . 2_656 C5 H11 3.4217 no . 2_656 C5 H25 3.2513 no . 4_555 C7 H6 3.6395 no . 2_646 C7 H6 3.5169 no . 2_656 C8 H6 3.5739 no . 2_656 C9 H4 3.4313 no . 2_646 C9 H4 3.6716 no . 2_656 C9 H6 3.6299 no . 2_656 C10 H4 3.5166 no . 2_646 C10 H5 3.4828 no . 2_646 C10 H25 3.1074 no . 3_666 C11 H1 3.6602 no . 2_646 C11 H5 3.6035 no . 2_646 C11 H24 3.5541 no . 3_666 C11 H25 3.4389 no . 3_666 C12 H2A 3.4567 no . 2_656 C13 H2A 3.4265 no . 2_656 C14 H1A 3.5152 no . 2_646 C14 H1A 3.5762 no . 2_656 C14 H1A 3.5864 no . 4_454 C14 H2A 3.6681 no . 2_656 C14 H14A 3.3233 no . 3_666 C14 H24 3.3528 no . . C15 H27 3.4992 no . 2_556 C15 H28A 3.6618 no . 2_546 C15 H28B 3.6352 no . 2_556 C15 H28C 3.4896 no . 2_546 C16 H27 3.6125 no . 2_546 C16 H27 3.4947 no . 2_556 C17 H20 3.6461 no . 2_546 C17 H20 3.5423 no . 2_556 C20 H20 3.5703 no . 2_546 C20 H20 3.5156 no . 2_556 C21 H18 3.6422 no . 2_546 C21 H18 3.5147 no . 2_556 C22 H18 3.6752 no . 2_546 C22 H18 3.4767 no . 2_556 C23 H18 3.6712 no . 2_556 C23 H19 3.6732 no . 2_546 C23 H19 3.6048 no . 2_556 C24 H1 3.4270 no . 4_454 C24 H11 3.3706 no . 3_666 C24 H19 3.6418 no . 2_546 C24 H19 3.4806 no . 2_556 C25 H5 3.3287 no . 4_454 C25 H10 3.2491 no . 3_666 C25 H11 3.5303 no . 3_666 C25 H19 3.5817 no . 2_556 C26 H2 3.4739 no . 2_546 C26 H2 3.5330 no . 2_556 C28 H2 3.6290 no . 2_546 C28 H2 3.5699 no . 2_556 C28 H28A 3.1266 no . 3_566 C28 H28B 3.6030 no . 3_566 C28 H28C 2.9797 no . 3_566 H1 Cl2 2.2073 no . . H1 C11 3.6602 no . 2_656 H1 C24 3.4270 no . 4_555 H1 H1A 3.2531 no . 3_767 H1 H11 3.3156 no . 2_656 H1 H14A 3.6763 no . 2_656 H1 H14A 3.4767 no . 4_555 H1 H14C 3.3561 no . 4_555 H1 H19 3.5741 no . 3_667 H1 H24 2.8721 no . 4_555 H1 H25 3.6501 no . 4_555 H1A Cl2 2.7404 no . 3_767 H1A C1 3.5877 no . 3_767 H1A C14 3.5762 no . 2_646 H1A C14 3.5152 no . 2_656 H1A C14 3.5864 no . 4_555 H1A H1 3.2531 no . 3_767 H1A H1A 2.9469 no . 3_767 H1A H14A 3.6264 no . 2_646 H1A H14A 3.3168 no . 2_656 H1A H14A 2.7661 no . 4_555 H1A H14B 2.9201 no . 2_646 H1A H14C 2.9979 no . 2_656 H1A H14C 3.5656 no . 4_555 H2 Cl1 2.2107 no . 3_667 H2 C26 3.5330 no . 2_546 H2 C26 3.4739 no . 2_556 H2 C28 3.5699 no . 2_546 H2 C28 3.6290 no . 2_556 H2 H5 3.3069 no . 3_667 H2 H28B 3.0268 no . 2_556 H2 H28C 2.8956 no . 2_546 H2A Cl2 3.1598 no . 3_767 H2A O4 2.7886 no . . H2A C12 3.4567 no . 2_646 H2A C13 3.4265 no . 2_646 H2A C14 3.6681 no . 2_646 H2A H13 3.4831 no . 2_646 H2A H14B 2.9771 no . 2_646 H2A H14C 3.2386 no . 2_656 H4 Cl1 3.4442 no . . H4 Cl3 3.1433 no . . H4 O1 2.8847 no . . H4 C9 3.6716 no . 2_646 H4 C9 3.4313 no . 2_656 H4 C10 3.5166 no . 2_656 H4 H9 3.6424 no . 2_646 H4 H9 3.5503 no . 2_656 H4 H10 3.6786 no . 2_656 H5 Cl1 2.7368 no . . H5 O1 3.5992 no . . H5 C10 3.4828 no . 2_656 H5 C11 3.6035 no . 2_656 H5 C25 3.3287 no . 4_555 H5 H2 3.3069 no . 3_667 H5 H10 3.3392 no . 2_656 H5 H11 3.5426 no . 2_656 H5 H19 3.4472 no . 3_667 H5 H24 3.6419 no . 4_555 H5 H25 2.8493 no . 4_555 H6 Cl3 2.8748 no . . H6 C7 3.5169 no . 2_646 H6 C7 3.6395 no . 2_656 H6 C8 3.5739 no . 2_646 H6 C9 3.6299 no . 2_646 H6 H7 3.5381 no . 2_646 H6 H7 3.6541 no . 2_656 H6 H9 3.5621 no . 2_646 H7 O4 2.7883 no . . H7 H6 3.6541 no . 2_646 H7 H6 3.5381 no . 2_656 H7 H13 3.5069 no . 2_656 H9 O1 3.1615 no . 2_656 H9 O2 3.3748 no . 2_646 H9 O3 3.4631 no . 2_646 H9 O4 3.3992 no . . H9 H4 3.5503 no . 2_646 H9 H4 3.6424 no . 2_656 H9 H6 3.5621 no . 2_656 H10 Cl1 3.4990 no . 2_646 H10 O1 3.0567 no . 2_656 H10 O2 3.6083 no . 2_646 H10 C4 3.6919 no . 2_656 H10 C5 3.5349 no . 2_646 H10 C25 3.2491 no . 3_666 H10 H4 3.6786 no . 2_646 H10 H5 3.3392 no . 2_646 H10 H25 2.3888 no . 3_666 H11 Cl2 3.4809 no . 2_646 H11 N1 3.3041 no . 2_646 H11 N1 3.6179 no . 2_656 H11 C1 3.6903 no . 2_656 H11 C5 3.4217 no . 2_646 H11 C24 3.3706 no . 3_666 H11 C25 3.5303 no . 3_666 H11 H1 3.3156 no . 2_646 H11 H5 3.5426 no . 2_646 H11 H14A 3.6718 no . 3_666 H11 H14B 3.6851 no . 3_666 H11 H24 2.7279 no . 3_666 H11 H25 3.0420 no . 3_666 H13 Cl3 3.1156 no . . H13 H2A 3.4831 no . 2_656 H13 H7 3.5069 no . 2_646 H14A N1 3.6775 no . 2_646 H14A C1 3.4493 no . 2_646 H14A C1 3.4417 no . 4_454 H14A C14 3.3233 no . 3_666 H14A H1 3.6763 no . 2_646 H14A H1 3.4767 no . 4_454 H14A H1A 3.3168 no . 2_646 H14A H1A 3.6264 no . 2_656 H14A H1A 2.7661 no . 4_454 H14A H11 3.6718 no . 3_666 H14A H14A 2.6749 no . 3_666 H14A H14B 3.1018 no . 3_666 H14A H24 3.4801 no . . H14B Cl2 3.2899 no . 4_464 H14B C1 3.2374 no . 2_656 H14B C2 3.2702 no . 2_656 H14B H1A 2.9201 no . 2_656 H14B H2A 2.9771 no . 2_656 H14B H11 3.6851 no . 3_666 H14B H14A 3.1018 no . 3_666 H14B H23 3.5273 no . . H14B H24 2.9903 no . . H14C Cl2 3.1763 no . 4_454 H14C O4 3.5656 no . 2_646 H14C C1 3.1351 no . 2_646 H14C C2 3.2742 no . 2_646 H14C H1 3.3561 no . 4_454 H14C H1A 2.9979 no . 2_646 H14C H1A 3.5656 no . 4_454 H14C H2A 3.2386 no . 2_646 H14C H23 3.4086 no . . H14C H24 3.0545 no . . H15 Cl1 2.8057 no . . H15 Cl1 3.6179 no . 3_667 H15 O1 3.0466 no . . H15 H28A 3.5506 no . 2_546 H15 H28A 3.5236 no . 2_556 H15 H28B 3.4351 no . 2_556 H15 H28B 2.9266 no . 4_555 H15 H28C 3.3757 no . 2_546 H16 Cl3 3.2034 no . . H16 O1 3.0252 no . . H16 O2 3.6456 no . . H16 O3 3.3379 no . . H18 O3 2.7548 no . 2_546 H18 O4 3.2359 no . 1_455 H18 C21 3.5147 no . 2_546 H18 C21 3.6422 no . 2_556 H18 C22 3.4767 no . 2_546 H18 C22 3.6752 no . 2_556 H18 C23 3.6712 no . 2_546 H18 H21 3.6127 no . 2_546 H19 Cl2 2.6337 no . 3_667 H19 C23 3.6048 no . 2_546 H19 C23 3.6732 no . 2_556 H19 C24 3.4806 no . 2_546 H19 C24 3.6418 no . 2_556 H19 C25 3.5817 no . 2_546 H19 H1 3.5741 no . 3_667 H19 H5 3.4472 no . 3_667 H20 O2 3.5428 no . 2_546 H20 O3 3.2070 no . 2_546 H20 C17 3.5423 no . 2_546 H20 C17 3.6461 no . 2_556 H20 C20 3.5156 no . 2_546 H20 C20 3.5703 no . 2_556 H21 Cl3 2.9225 no . . H21 O3 3.1923 no . . H21 H18 3.6127 no . 2_556 H23 Cl3 3.0630 no . . H23 O4 3.4231 no . 2_646 H23 H14B 3.5273 no . . H23 H14C 3.4086 no . . H24 Cl2 3.5956 no . 4_454 H24 Cl2 3.6673 no . 4_464 H24 N1 3.3182 no . 4_454 H24 C11 3.5541 no . 3_666 H24 C14 3.3528 no . . H24 H1 2.8721 no . 4_454 H24 H5 3.6419 no . 4_454 H24 H11 2.7279 no . 3_666 H24 H14A 3.4801 no . . H24 H14B 2.9903 no . . H24 H14C 3.0545 no . . H25 O1 3.4681 no . 4_454 H25 N1 3.6899 no . 4_454 H25 C5 3.2513 no . 4_454 H25 C10 3.1074 no . 3_666 H25 C11 3.4389 no . 3_666 H25 H1 3.6501 no . 4_454 H25 H5 2.8493 no . 4_454 H25 H10 2.3888 no . 3_666 H25 H11 3.0420 no . 3_666 H27 O2 2.8322 no . 2_546 H27 C15 3.4992 no . 2_546 H27 C16 3.4947 no . 2_546 H27 C16 3.6125 no . 2_556 H28A Cl1 3.4933 no . 2_546 H28A O2 2.7595 no . 2_546 H28A C15 3.6618 no . 2_556 H28A C28 3.1266 no . 3_566 H28A H15 3.5236 no . 2_546 H28A H15 3.5506 no . 2_556 H28A H28A 3.1371 no . 3_566 H28A H28B 3.2382 no . 3_566 H28A H28C 2.5263 no . 3_566 H28B Cl1 2.9174 no . 4_454 H28B O1 3.1357 no . 4_454 H28B N2 3.4113 no . 2_546 H28B C15 3.6352 no . 2_546 H28B C28 3.6030 no . 3_566 H28B H2 3.0268 no . 2_546 H28B H15 3.4351 no . 2_546 H28B H15 2.9266 no . 4_454 H28B H28A 3.2382 no . 3_566 H28B H28C 3.0965 no . 3_566 H28C Cl1 3.1716 no . 4_464 H28C O1 3.5372 no . 4_454 H28C O2 3.6188 no . 4_464 H28C N2 3.2221 no . 2_556 H28C C15 3.4896 no . 2_556 H28C C28 2.9797 no . 3_566 H28C H2 2.8956 no . 2_556 H28C H15 3.3757 no . 2_556 H28C H28A 2.5263 no . 3_566 H28C H28B 3.0965 no . 3_566 H28C H28C 2.8366 no . 3_566 #============================================================================== loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_D _geom_hbond_site_symmetry_H _geom_hbond_site_symmetry_A _geom_hbond_distance_DA _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_angle_DHA _geom_hbond_publ_flag N1 H1 Cl2 . . . 3.036(4) 0.880 2.207 156.7 no N2 H2 Cl1 . . 3_667 3.081(4) 0.880 2.211 169.9 no data_4-Me-SP2 _database_code_depnum_ccdc_archive 'CCDC 888279' #TrackingRef 'CCDC 888279.cif' #============================================================================== # CHEMICAL DATA _chemical_formula_sum 'C14 H16.50 Cl1.50 N O' _chemical_formula_moiety 'C14 H16.50 Cl1.50 N O' _chemical_formula_weight 267.97 _chemical_melting_point ? #============================================================================== # CRYSTAL DATA _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 +X,+Y,+Z 2 -X,-Y,-Z #------------------------------------------------------------------------------ _cell_length_a 4.8772(2) _cell_length_b 16.2559(7) _cell_length_c 18.5704(8) _cell_angle_alpha 80.839(3) _cell_angle_beta 87.297(2) _cell_angle_gamma 84.649(3) _cell_volume 1446.41(11) _cell_formula_units_Z 4 _cell_measurement_reflns_used 4244 _cell_measurement_theta_min 3.38 _cell_measurement_theta_max 67.97 _cell_measurement_temperature 123 #------------------------------------------------------------------------------ _exptl_crystal_description needle _exptl_crystal_colour yellow _exptl_crystal_size_max 0.250 _exptl_crystal_size_mid 0.050 _exptl_crystal_size_min 0.020 _exptl_crystal_density_diffrn 1.230 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 564.00 _exptl_absorpt_coefficient_mu 3.072 _exptl_absorpt_correction_type none #============================================================================== # EXPERIMENTAL DATA _diffrn_ambient_temperature 123 _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54187 _diffrn_measurement_device_type 'Rigaku R-AXIS RAPID' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.000 _diffrn_reflns_number 14825 _diffrn_reflns_av_R_equivalents 0.1142 _diffrn_reflns_theta_max 68.25 _diffrn_reflns_theta_full 68.25 _diffrn_measured_fraction_theta_max 0.967 _diffrn_measured_fraction_theta_full 0.967 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_limit_l_max 22 _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_decay_% ? #============================================================================== # REFINEMENT DATA _refine_special_details ; Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F^2^. R-factor (gt) are based on F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 5102 _reflns_number_gt 1412 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0884 _refine_ls_wR_factor_ref 0.1799 _refine_ls_number_restraints 0 _refine_ls_hydrogen_treatment constr _refine_ls_number_reflns 5102 _refine_ls_number_parameters 317 _refine_ls_goodness_of_fit_ref 1.034 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0300P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_ls_shift/su_max 0.000 _refine_diff_density_max 0.420 _refine_diff_density_min -0.270 _refine_ls_extinction_method none _refine_ls_extinction_coef ? 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 for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; N N 0.0311 0.0180 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; Cl Cl 0.3639 0.7018 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; O O 0.0492 0.0322 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; H H 0.0000 0.0000 ; International Tables for Crystallography (1992, Vol. C, Table 6.1.1.4) ; #============================================================================== # ATOMIC COORDINATES AND THERMAL PARAMETERS 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 0.4303(3) 0.11986(8) -0.04982(7) 0.0653(5) Uani 1.0 2 d . . . Cl2 Cl 0.5604(3) 0.36375(9) 0.08831(8) 0.0854(6) Uani 1.0 2 d . . . O1 O -0.9453(16) 0.3493(4) 0.1970(4) 0.239(4) Uani 1.0 2 d . . . N1 N 1.1740(9) 0.3887(4) -0.0405(3) 0.0602(14) Uani 1.0 2 d . . . N2 N -0.1642(10) 0.0757(5) 0.0719(3) 0.0664(15) Uani 1.0 2 d . . . C1 C 1.0690(14) 0.4548(4) -0.0846(4) 0.0692(18) Uani 1.0 2 d . . . C2 C 0.8813(14) 0.4464(4) -0.1339(4) 0.0729(19) Uani 1.0 2 d . . . C3 C 0.7954(12) 0.3671(5) -0.1384(4) 0.0580(16) Uani 1.0 2 d . . . C4 C 0.9109(12) 0.3004(4) -0.0910(3) 0.0588(17) Uani 1.0 2 d . . . C5 C 1.0965(13) 0.3127(5) -0.0423(3) 0.0618(17) Uani 1.0 2 d . . . C6 C 0.5941(14) 0.3614(4) -0.1959(4) 0.0709(19) Uani 1.0 2 d . . . C7 C 0.4789(14) 0.2944(5) -0.2006(4) 0.075(2) Uani 1.0 2 d . . . C8 C 0.2795(12) 0.2831(5) -0.2559(4) 0.0620(18) Uani 1.0 2 d . . . C9 C 0.1967(14) 0.3433(4) -0.3146(4) 0.0762(19) Uani 1.0 2 d . . . C10 C 0.0124(14) 0.3259(5) -0.3648(4) 0.081(2) Uani 1.0 2 d . . . C11 C -0.0956(13) 0.2485(5) -0.3565(4) 0.0719(19) Uani 1.0 2 d . . . C12 C -0.0114(13) 0.1908(5) -0.2977(4) 0.0736(19) Uani 1.0 2 d . . . C13 C 0.1683(14) 0.2060(5) -0.2476(4) 0.075(2) Uani 1.0 2 d . . . C14 C -0.2835(12) 0.2289(4) -0.4128(3) 0.099(3) Uani 1.0 2 d . . . C15 C -0.0042(14) 0.0102(4) 0.1024(4) 0.0620(18) Uani 1.0 2 d . . . C16 C 0.1835(13) 0.0207(5) 0.1508(4) 0.0683(19) Uani 1.0 2 d . . . C17 C 0.2074(14) 0.1005(6) 0.1672(4) 0.072(3) Uani 1.0 2 d . . . C18 C 0.0363(15) 0.1677(4) 0.1331(4) 0.072(2) Uani 1.0 2 d . . . C19 C -0.1468(14) 0.1524(5) 0.0858(4) 0.0694(19) Uani 1.0 2 d . . . C20 C 0.4104(17) 0.1232(6) 0.2208(5) 0.105(3) Uani 1.0 2 d . . . C21 C 0.5461(17) 0.0730(5) 0.2611(4) 0.103(3) Uani 1.0 2 d . . . C22 C 0.7534(14) 0.0960(6) 0.3153(4) 0.073(2) Uani 1.0 2 d . . . C23 C 0.8131(14) 0.1768(5) 0.3218(4) 0.077(2) Uani 1.0 2 d . . . C24 C 0.9971(13) 0.1881(4) 0.3731(4) 0.0702(19) Uani 1.0 2 d . . . C25 C 1.1305(12) 0.1218(5) 0.4174(3) 0.0582(17) Uani 1.0 2 d . . . C26 C 1.0667(12) 0.0425(5) 0.4092(3) 0.0653(18) Uani 1.0 2 d . . . C27 C 0.8811(13) 0.0305(4) 0.3595(4) 0.0672(18) Uani 1.0 2 d . . . C28 C 1.3264(11) 0.1347(4) 0.4746(3) 0.0756(19) Uani 1.0 2 d . . . H1 H 1.2977 0.3950 -0.0093 0.0723 Uiso 1.0 2 calc R . . H1A H 1.1253 0.5085 -0.0818 0.0831 Uiso 1.0 2 calc R . . H2 H -0.2874 0.0679 0.0411 0.0796 Uiso 1.0 2 calc R . . H2A H 0.8074 0.4942 -0.1656 0.0875 Uiso 1.0 2 calc R . . H4 H 0.8604 0.2457 -0.0923 0.0706 Uiso 1.0 2 calc R . . H5 H 1.1720 0.2665 -0.0092 0.0742 Uiso 1.0 2 calc R . . H6 H 0.5495 0.4099 -0.2306 0.0851 Uiso 1.0 2 calc R . . H7 H 0.5260 0.2470 -0.1650 0.0898 Uiso 1.0 2 calc R . . H9 H 0.2657 0.3968 -0.3208 0.0915 Uiso 1.0 2 calc R . . H10 H -0.0393 0.3674 -0.4050 0.0971 Uiso 1.0 2 calc R . . H12 H -0.0814 0.1374 -0.2914 0.0884 Uiso 1.0 2 calc R . . H13 H 0.2168 0.1640 -0.2074 0.0906 Uiso 1.0 2 calc R . . H14A H -0.1856 0.2329 -0.4604 0.1194 Uiso 1.0 2 calc R . . H14B H -0.4473 0.2689 -0.4162 0.1194 Uiso 1.0 2 calc R . . H14C H -0.3394 0.1721 -0.3984 0.1194 Uiso 1.0 2 calc R . . H15 H -0.0213 -0.0437 0.0903 0.0744 Uiso 1.0 2 calc R . . H16 H 0.2979 -0.0258 0.1734 0.0819 Uiso 1.0 2 calc R . . H18 H 0.0486 0.2228 0.1431 0.0863 Uiso 1.0 2 calc R . . H19 H -0.2650 0.1974 0.0621 0.0832 Uiso 1.0 2 calc R . . H20 H 0.4280 0.1807 0.2217 0.1264 Uiso 1.0 2 calc R . . H21 H 0.5277 0.0154 0.2605 0.1231 Uiso 1.0 2 calc R . . H23 H 0.7279 0.2238 0.2913 0.0919 Uiso 1.0 2 calc R . . H24 H 1.0327 0.2434 0.3780 0.0842 Uiso 1.0 2 calc R . . H26 H 1.1540 -0.0047 0.4389 0.0784 Uiso 1.0 2 calc R . . H27 H 0.8411 -0.0248 0.3559 0.0806 Uiso 1.0 2 calc R . . H28A H 1.3205 0.0889 0.5157 0.0907 Uiso 1.0 2 calc R . . H28B H 1.2716 0.1880 0.4917 0.0907 Uiso 1.0 2 calc R . . H28C H 1.5141 0.1355 0.4533 0.0907 Uiso 1.0 2 calc R . . Cl3A Cl -0.3024 0.4374 0.4161 0.563(13) Uani 0.516(8) 2 d . . . O2 O -0.8281 0.4227 0.3700 0.517(11) Uani 1.0 2 d . . . Cl3B Cl -0.3766 0.4063 0.3092 0.532(14) Uani 0.484(8) 2 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_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 Cl1 0.0672(11) 0.0693(10) 0.0596(10) -0.0043(8) -0.0134(8) -0.0079(8) Cl2 0.0819(13) 0.0833(12) 0.0951(13) 0.0007(10) -0.0211(10) -0.0259(10) O1 0.305(9) 0.154(6) 0.248(7) -0.063(6) -0.048(7) 0.035(6) N1 0.051(4) 0.072(4) 0.061(4) -0.014(3) -0.007(3) -0.013(3) N2 0.059(4) 0.099(5) 0.046(4) -0.021(4) -0.010(3) -0.012(4) C1 0.081(6) 0.055(5) 0.074(5) -0.013(4) -0.012(4) -0.012(4) C2 0.076(6) 0.060(5) 0.079(5) 0.007(4) -0.019(4) -0.001(4) C3 0.051(5) 0.070(5) 0.056(5) -0.009(4) -0.009(4) -0.013(4) C4 0.060(5) 0.061(5) 0.054(4) -0.005(4) 0.004(4) -0.006(4) C5 0.060(5) 0.075(5) 0.048(5) -0.007(4) -0.004(4) 0.000(4) C6 0.072(5) 0.070(5) 0.071(5) -0.008(4) 0.015(4) -0.013(4) C7 0.069(5) 0.086(6) 0.068(5) -0.008(5) 0.009(4) -0.009(5) C8 0.043(4) 0.108(6) 0.038(4) -0.010(4) -0.011(4) -0.017(4) C9 0.080(6) 0.090(6) 0.062(5) -0.011(5) 0.006(4) -0.022(5) C10 0.069(5) 0.117(7) 0.058(5) -0.011(5) -0.012(4) -0.012(5) C11 0.058(5) 0.099(6) 0.062(5) -0.000(5) -0.007(4) -0.025(5) C12 0.063(5) 0.092(6) 0.072(5) -0.011(4) -0.006(4) -0.027(5) C13 0.063(5) 0.099(6) 0.065(5) -0.011(5) -0.004(4) -0.011(5) C14 0.072(5) 0.159(7) 0.081(5) 0.001(5) -0.017(4) -0.063(5) C15 0.063(5) 0.074(5) 0.050(4) -0.006(4) 0.000(4) -0.011(4) C16 0.050(5) 0.101(6) 0.049(5) -0.005(4) -0.004(4) 0.001(4) C17 0.040(5) 0.143(8) 0.045(5) -0.037(5) -0.005(4) -0.033(5) C18 0.068(6) 0.078(5) 0.068(5) -0.010(5) 0.008(4) -0.009(5) C19 0.059(5) 0.091(6) 0.052(5) -0.006(5) -0.002(4) 0.004(4) C20 0.082(7) 0.129(8) 0.088(7) 0.018(6) 0.047(5) 0.007(6) C21 0.094(7) 0.117(7) 0.076(6) 0.011(6) 0.039(5) 0.024(5) C22 0.053(5) 0.137(8) 0.033(5) -0.020(5) -0.012(4) -0.011(5) C23 0.069(6) 0.099(6) 0.053(5) 0.006(5) -0.001(4) 0.006(5) C24 0.063(5) 0.081(5) 0.067(5) -0.013(4) -0.011(4) -0.007(4) C25 0.042(4) 0.085(5) 0.049(4) -0.006(4) -0.012(3) -0.008(4) C26 0.057(5) 0.089(6) 0.050(5) -0.007(4) -0.007(4) -0.010(4) C27 0.073(5) 0.093(6) 0.040(4) -0.014(4) -0.003(4) -0.019(4) C28 0.059(5) 0.111(6) 0.061(4) -0.011(4) -0.010(4) -0.023(4) Cl3A 1.00(4) 0.178(8) 0.482(16) -0.146(14) -0.26(2) 0.173(9) O2 0.318(12) 0.125(7) 1.02(3) -0.028(8) -0.092(16) 0.194(12) Cl3B 0.90(4) 0.106(6) 0.57(3) 0.022(12) -0.30(3) 0.059(9) #============================================================================== _computing_data_collection 'RAPID AUTO (Rigaku, ????)' _computing_cell_refinement 'RAPID AUTO' _computing_data_reduction 'RAPID AUTO' _computing_structure_solution 'SIR2004 (Burla, et al., 2005)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_publication_material 'CrystalStructure 4.0 (Rigaku, 2010)' _computing_molecular_graphics 'CrystalStructure 4.0' #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 N1 C1 1.321(8) yes . . N1 C5 1.330(9) yes . . N2 C15 1.326(8) yes . . N2 C19 1.324(11) yes . . C1 C2 1.355(10) yes . . C2 C3 1.408(10) yes . . C3 C4 1.377(8) yes . . C3 C6 1.503(9) yes . . C4 C5 1.358(9) yes . . C6 C7 1.289(10) yes . . C7 C8 1.490(10) yes . . C8 C9 1.392(9) yes . . C8 C13 1.396(11) yes . . C9 C10 1.403(10) yes . . C10 C11 1.392(12) yes . . C11 C12 1.373(10) yes . . C11 C14 1.512(10) yes . . C12 C13 1.372(10) yes . . C15 C16 1.353(10) yes . . C16 C17 1.395(13) yes . . C17 C18 1.396(10) yes . . C17 C20 1.545(12) yes . . C18 C19 1.347(10) yes . . C20 C21 1.190(11) yes . . C21 C22 1.568(12) yes . . C22 C23 1.397(13) yes . . C22 C27 1.358(10) yes . . C23 C24 1.383(10) yes . . C24 C25 1.378(9) yes . . C25 C26 1.386(11) yes . . C25 C28 1.513(9) yes . . C26 C27 1.371(9) yes . . N1 H1 0.880 no . . N2 H2 0.880 no . . C1 H1A 0.950 no . . C2 H2A 0.950 no . . C4 H4 0.950 no . . C5 H5 0.950 no . . C6 H6 0.950 no . . C7 H7 0.950 no . . C9 H9 0.950 no . . C10 H10 0.950 no . . C12 H12 0.950 no . . C13 H13 0.950 no . . C14 H14A 0.980 no . . C14 H14B 0.980 no . . C14 H14C 0.980 no . . C15 H15 0.950 no . . C16 H16 0.950 no . . C18 H18 0.950 no . . C19 H19 0.950 no . . C20 H20 0.950 no . . C21 H21 0.950 no . . C23 H23 0.950 no . . C24 H24 0.950 no . . C26 H26 0.950 no . . C27 H27 0.950 no . . C28 H28A 0.980 no . . C28 H28B 0.980 no . . C28 H28C 0.980 no . . 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 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 C1 N1 C5 121.3(6) yes . . . C15 N2 C19 122.8(6) yes . . . N1 C1 C2 120.4(6) yes . . . C1 C2 C3 120.4(6) yes . . . C2 C3 C4 116.8(6) yes . . . C2 C3 C6 117.8(6) yes . . . C4 C3 C6 125.4(7) yes . . . C3 C4 C5 120.3(6) yes . . . N1 C5 C4 120.9(6) yes . . . C3 C6 C7 123.5(6) yes . . . C6 C7 C8 127.0(6) yes . . . C7 C8 C9 125.1(7) yes . . . C7 C8 C13 116.9(6) yes . . . C9 C8 C13 118.0(6) yes . . . C8 C9 C10 120.7(7) yes . . . C9 C10 C11 120.9(6) yes . . . C10 C11 C12 116.9(7) yes . . . C10 C11 C14 120.5(6) yes . . . C12 C11 C14 122.6(7) yes . . . C11 C12 C13 123.7(7) yes . . . C8 C13 C12 119.8(6) yes . . . N2 C15 C16 119.5(7) yes . . . C15 C16 C17 119.4(6) yes . . . C16 C17 C18 119.0(7) yes . . . C16 C17 C20 125.9(7) yes . . . C18 C17 C20 115.1(8) yes . . . C17 C18 C19 118.3(7) yes . . . N2 C19 C18 120.9(6) yes . . . C17 C20 C21 124.0(9) yes . . . C20 C21 C22 124.0(9) yes . . . C21 C22 C23 125.8(7) yes . . . C21 C22 C27 115.7(8) yes . . . C23 C22 C27 118.5(7) yes . . . C22 C23 C24 119.6(6) yes . . . C23 C24 C25 122.2(7) yes . . . C24 C25 C26 116.6(6) yes . . . C24 C25 C28 121.8(7) yes . . . C26 C25 C28 121.5(6) yes . . . C25 C26 C27 121.9(6) yes . . . C22 C27 C26 121.2(7) yes . . . C1 N1 H1 119.346 no . . . C5 N1 H1 119.343 no . . . C15 N2 H2 118.570 no . . . C19 N2 H2 118.588 no . . . N1 C1 H1A 119.814 no . . . C2 C1 H1A 119.824 no . . . C1 C2 H2A 119.820 no . . . C3 C2 H2A 119.820 no . . . C3 C4 H4 119.875 no . . . C5 C4 H4 119.873 no . . . N1 C5 H5 119.559 no . . . C4 C5 H5 119.563 no . . . C3 C6 H6 118.275 no . . . C7 C6 H6 118.269 no . . . C6 C7 H7 116.513 no . . . C8 C7 H7 116.516 no . . . C8 C9 H9 119.626 no . . . C10 C9 H9 119.630 no . . . C9 C10 H10 119.550 no . . . C11 C10 H10 119.554 no . . . C11 C12 H12 118.162 no . . . C13 C12 H12 118.153 no . . . C8 C13 H13 120.099 no . . . C12 C13 H13 120.102 no . . . C11 C14 H14A 109.467 no . . . C11 C14 H14B 109.471 no . . . C11 C14 H14C 109.479 no . . . H14A C14 H14B 109.472 no . . . H14A C14 H14C 109.466 no . . . H14B C14 H14C 109.472 no . . . N2 C15 H15 120.236 no . . . C16 C15 H15 120.238 no . . . C15 C16 H16 120.315 no . . . C17 C16 H16 120.321 no . . . C17 C18 H18 120.854 no . . . C19 C18 H18 120.854 no . . . N2 C19 H19 119.537 no . . . C18 C19 H19 119.525 no . . . C17 C20 H20 118.002 no . . . C21 C20 H20 118.007 no . . . C20 C21 H21 118.020 no . . . C22 C21 H21 118.023 no . . . C22 C23 H23 120.202 no . . . C24 C23 H23 120.190 no . . . C23 C24 H24 118.919 no . . . C25 C24 H24 118.922 no . . . C25 C26 H26 119.071 no . . . C27 C26 H26 119.057 no . . . C22 C27 H27 119.379 no . . . C26 C27 H27 119.394 no . . . C25 C28 H28A 109.474 no . . . C25 C28 H28B 109.471 no . . . C25 C28 H28C 109.461 no . . . H28A C28 H28B 109.473 no . . . H28A C28 H28C 109.472 no . . . H28B C28 H28C 109.476 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 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 C1 N1 C5 C4 1.5(8) no . . . . C5 N1 C1 C2 -1.0(9) no . . . . C15 N2 C19 C18 -0.7(9) no . . . . C19 N2 C15 C16 1.0(9) no . . . . N1 C1 C2 C3 0.2(9) no . . . . C1 C2 C3 C4 -0.0(9) no . . . . C1 C2 C3 C6 -178.0(5) no . . . . C2 C3 C4 C5 0.5(8) no . . . . C2 C3 C6 C7 -172.6(6) no . . . . C4 C3 C6 C7 9.7(10) no . . . . C6 C3 C4 C5 178.3(5) no . . . . C3 C4 C5 N1 -1.3(9) no . . . . C3 C6 C7 C8 -179.5(5) no . . . . C6 C7 C8 C9 3.7(11) no . . . . C6 C7 C8 C13 -176.2(6) no . . . . C7 C8 C9 C10 178.5(6) no . . . . C7 C8 C13 C12 -178.4(5) no . . . . C9 C8 C13 C12 1.6(9) no . . . . C13 C8 C9 C10 -1.6(9) no . . . . C8 C9 C10 C11 1.1(10) no . . . . C9 C10 C11 C12 -0.5(10) no . . . . C9 C10 C11 C14 -177.1(6) no . . . . C10 C11 C12 C13 0.6(10) no . . . . C14 C11 C12 C13 177.1(6) no . . . . C11 C12 C13 C8 -1.2(10) no . . . . N2 C15 C16 C17 -0.7(9) no . . . . C15 C16 C17 C18 0.1(9) no . . . . C15 C16 C17 C20 -179.9(5) no . . . . C16 C17 C18 C19 0.3(9) no . . . . C16 C17 C20 C21 -9.8(11) no . . . . C18 C17 C20 C21 170.2(7) no . . . . C20 C17 C18 C19 -179.7(6) no . . . . C17 C18 C19 N2 -0.0(10) no . . . . C17 C20 C21 C22 179.6(6) no . . . . C20 C21 C22 C23 -2.2(12) no . . . . C20 C21 C22 C27 177.1(8) no . . . . C21 C22 C23 C24 178.7(6) no . . . . C21 C22 C27 C26 -179.9(5) no . . . . C23 C22 C27 C26 -0.6(9) no . . . . C27 C22 C23 C24 -0.6(9) no . . . . C22 C23 C24 C25 1.6(9) no . . . . C23 C24 C25 C26 -1.4(9) no . . . . C23 C24 C25 C28 -178.5(5) no . . . . C24 C25 C26 C27 0.2(8) no . . . . C28 C25 C26 C27 177.4(5) no . . . . C25 C26 C27 C22 0.7(9) no . . . . loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_publ_flag _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 N1 C3 2.735(8) no . . N2 C17 2.691(9) no . . C1 C4 2.715(9) no . . C2 C5 2.698(9) no . . C4 C7 3.017(9) no . . C6 C9 3.069(10) no . . C8 C11 2.829(10) no . . C9 C12 2.732(10) no . . C10 C13 2.764(9) no . . C15 C18 2.736(10) no . . C16 C19 2.712(10) no . . C16 C21 3.037(11) no . . C18 C21 3.589(10) no . . C20 C23 3.054(12) no . . C20 C27 3.584(10) no . . C22 C25 2.807(10) no . . C23 C26 2.736(9) no . . C24 C27 2.728(10) no . . Cl1 N2 3.645(5) no . . Cl1 N2 3.029(5) no . 1_655 Cl1 N2 3.633(7) no . 2_555 Cl1 C5 3.415(7) no . 1_455 Cl1 C7 3.671(7) no . . Cl1 C15 3.378(7) no . 2_555 Cl1 C15 3.544(7) no . 2_655 Cl1 C16 3.538(7) no . 2_655 Cl1 C19 3.464(7) no . 1_655 Cl2 O1 3.115(8) no . 1_655 Cl2 O1 3.185(8) no . 1_755 Cl2 N1 3.068(5) no . 1_455 Cl2 C1 3.590(7) no . 2_765 Cl2 C5 3.633(7) no . 1_455 Cl2 C5 3.612(6) no . . Cl2 C19 3.601(8) no . 1_655 O1 Cl2 3.185(8) no . 1_355 O1 Cl2 3.115(8) no . 1_455 O1 C1 3.536(9) no . 2_565 O1 C2 3.380(9) no . 2_565 O1 C18 3.363(10) no . 1_455 O1 C23 3.593(10) no . 1_355 O1 O2 3.686(8) no . . O1 Cl3B 3.076(7) no . 1_455 N1 Cl2 3.068(5) no . 1_655 N1 C3 3.479(8) no . 1_655 N1 C6 3.522(8) no . 1_655 N2 Cl1 3.029(5) no . 1_455 N2 Cl1 3.645(5) no . . N2 Cl1 3.633(7) no . 2_555 N2 C16 3.569(8) no . 1_455 N2 C17 3.488(8) no . 1_455 N2 C20 3.519(10) no . 1_455 C1 Cl2 3.590(7) no . 2_765 C1 O1 3.536(9) no . 2_565 C1 C1 3.685(10) no . 2_765 C1 C6 3.593(9) no . 1_655 C2 O1 3.380(9) no . 2_565 C3 N1 3.479(8) no . 1_455 C3 C7 3.630(9) no . 1_655 C3 C8 3.473(9) no . 1_655 C4 C7 3.363(9) no . 1_655 C4 C8 3.515(9) no . 1_655 C4 C13 3.621(9) no . 1_655 C5 Cl1 3.415(7) no . 1_655 C5 Cl2 3.612(6) no . . C5 Cl2 3.633(7) no . 1_655 C5 C6 3.693(9) no . 1_655 C5 C7 3.445(9) no . 1_655 C5 C19 3.493(9) no . 1_655 C6 N1 3.522(8) no . 1_455 C6 C1 3.593(9) no . 1_455 C6 C5 3.693(9) no . 1_455 C6 C8 3.653(9) no . 1_655 C6 C9 3.608(9) no . 1_655 C7 Cl1 3.671(7) no . . C7 C3 3.630(9) no . 1_455 C7 C4 3.363(9) no . 1_455 C7 C5 3.445(9) no . 1_455 C7 C11 3.616(10) no . 1_655 C7 C12 3.468(10) no . 1_655 C7 C13 3.655(9) no . 1_655 C8 C3 3.473(9) no . 1_455 C8 C4 3.515(9) no . 1_455 C8 C6 3.653(9) no . 1_455 C8 C11 3.545(9) no . 1_655 C8 C14 3.700(9) no . 1_655 C9 C6 3.608(9) no . 1_455 C9 C14 3.603(9) no . 1_655 C11 C7 3.616(10) no . 1_455 C11 C8 3.545(9) no . 1_455 C12 C7 3.468(10) no . 1_455 C13 C4 3.621(9) no . 1_455 C13 C7 3.655(9) no . 1_455 C14 C8 3.700(9) no . 1_455 C14 C9 3.603(9) no . 1_455 C14 C28 3.503(9) no . 1_354 C15 Cl1 3.378(7) no . 2_555 C15 Cl1 3.544(7) no . 2_655 C16 Cl1 3.538(7) no . 2_655 C16 N2 3.569(8) no . 1_655 C17 N2 3.488(8) no . 1_655 C17 C19 3.543(10) no . 1_655 C17 C21 3.625(11) no . 1_455 C17 C22 3.445(9) no . 1_455 C17 C23 3.696(10) no . 1_455 C18 O1 3.363(10) no . 1_655 C18 C20 3.473(11) no . 1_455 C18 C21 3.567(11) no . 1_455 C18 C22 3.648(9) no . 1_455 C18 C23 3.642(10) no . 1_455 C19 Cl1 3.464(7) no . 1_455 C19 Cl2 3.601(8) no . 1_455 C19 C5 3.493(9) no . 1_455 C19 C17 3.543(10) no . 1_455 C19 C20 3.237(10) no . 1_455 C19 C21 3.616(10) no . 1_455 C20 N2 3.519(10) no . 1_655 C20 C18 3.473(11) no . 1_655 C20 C19 3.237(10) no . 1_655 C20 C22 3.609(10) no . 1_455 C20 C23 3.507(11) no . 1_455 C20 C24 3.632(11) no . 1_455 C21 C17 3.625(11) no . 1_655 C21 C18 3.567(11) no . 1_655 C21 C19 3.616(10) no . 1_655 C21 C25 3.610(10) no . 1_455 C21 C26 3.528(10) no . 1_455 C22 C17 3.445(9) no . 1_655 C22 C18 3.648(9) no . 1_655 C22 C20 3.609(10) no . 1_655 C22 C25 3.531(9) no . 1_455 C22 C28 3.640(9) no . 1_455 C23 O1 3.593(10) no . 1_755 C23 C17 3.696(10) no . 1_655 C23 C18 3.642(10) no . 1_655 C23 C20 3.507(11) no . 1_655 C23 C28 3.633(8) no . 1_455 C24 C20 3.632(11) no . 1_655 C25 C21 3.610(10) no . 1_655 C25 C22 3.531(9) no . 1_655 C26 C21 3.528(10) no . 1_655 C26 C26 3.490(8) no . 2_756 C28 C14 3.503(9) no . 1_756 C28 C22 3.640(9) no . 1_655 C28 C23 3.633(8) no . 1_655 Cl3A O2 2.78392(11) no . . Cl3A O2 2.43236(10) no . 1_655 O2 O1 3.686(8) no . . O2 Cl3A 2.43236(10) no . 1_455 O2 Cl3A 2.78392(11) no . . O2 Cl3B 3.00266(11) no . 1_455 O2 Cl3B 2.43860(9) no . . Cl3B O1 3.076(7) no . 1_655 Cl3B O2 2.43860(9) no . . Cl3B O2 3.00266(11) no . 1_655 N1 H2A 3.1755 no . . N1 H4 3.1913 no . . N2 H16 3.1740 no . . N2 H18 3.1833 no . . C1 H5 3.1623 no . . C2 H1 3.1127 no . . C2 H4 3.2409 no . . C2 H6 2.6441 no . . C3 H1A 3.2562 no . . C3 H5 3.2274 no . . C3 H7 2.5736 no . . C4 H1 3.1274 no . . C4 H2A 3.2361 no . . C4 H6 3.3726 no . . C4 H7 2.6629 no . . C5 H1A 3.1654 no . . C6 H2A 2.6299 no . . C6 H4 2.7497 no . . C6 H9 2.8328 no . . C7 H4 2.7763 no . . C7 H9 2.7471 no . . C7 H13 2.5967 no . . C8 H6 2.6591 no . . C8 H10 3.2800 no . . C8 H12 3.2437 no . . C9 H6 2.7749 no . . C9 H7 3.3648 no . . C9 H13 3.2535 no . . C10 H12 3.2132 no . . C10 H14A 2.7671 no . . C10 H14B 2.7687 no . . C10 H14C 3.3144 no . . C11 H9 3.2820 no . . C11 H13 3.2667 no . . C12 H10 3.2186 no . . C12 H14A 3.1291 no . . C12 H14B 3.1652 no . . C12 H14C 2.5892 no . . C13 H7 2.5772 no . . C13 H9 3.2513 no . . C14 H10 2.6710 no . . C14 H12 2.6717 no . . C15 H19 3.1739 no . . C16 H2 3.1029 no . . C16 H18 3.2706 no . . C16 H20 3.4263 no . . C16 H21 2.6863 no . . C17 H2 3.5711 no . . C17 H15 3.2363 no . . C17 H19 3.2189 no . . C17 H21 2.5389 no . . C18 H2 3.1082 no . . C18 H16 3.2673 no . . C18 H20 2.6233 no . . C19 H15 3.1780 no . . C20 H16 2.8139 no . . C20 H18 2.6041 no . . C20 H23 2.8509 no . . C21 H16 2.8427 no . . C21 H23 2.8283 no . . C21 H27 2.5718 no . . C22 H20 2.5542 no . . C22 H24 3.2556 no . . C22 H26 3.2253 no . . C23 H20 2.6947 no . . C23 H21 3.4501 no . . C23 H27 3.2290 no . . C24 H26 3.2136 no . . C24 H28A 3.2649 no . . C24 H28B 2.6294 no . . C24 H28C 2.9745 no . . C25 H23 3.2680 no . . C25 H27 3.2589 no . . C26 H24 3.2137 no . . C26 H28A 2.6255 no . . C26 H28B 3.2670 no . . C26 H28C 2.9820 no . . C27 H21 2.6325 no . . C27 H23 3.2282 no . . C28 H24 2.6737 no . . C28 H26 2.6777 no . . H1 H1A 2.2256 no . . H1 H5 2.2311 no . . H1A H2A 2.2998 no . . H2 H15 2.2260 no . . H2 H19 2.2141 no . . H2A H6 2.4318 no . . H4 H5 2.3002 no . . H4 H7 2.1619 no . . H6 H7 2.7430 no . . H6 H9 2.2687 no . . H7 H13 2.3547 no . . H9 H10 2.3407 no . . H10 H14A 2.7251 no . . H10 H14B 2.7032 no . . H12 H13 2.2972 no . . H12 H14A 3.3124 no . . H12 H14B 3.3506 no . . H12 H14C 2.3665 no . . H15 H16 2.3106 no . . H16 H21 2.2313 no . . H18 H19 2.3027 no . . H18 H20 2.3923 no . . H20 H21 2.6738 no . . H20 H23 2.2262 no . . H21 H27 2.3670 no . . H23 H24 2.3205 no . . H24 H28A 3.5289 no . . H24 H28B 2.4604 no . . H24 H28C 3.0495 no . . H26 H27 2.2991 no . . H26 H28A 2.4587 no . . H26 H28B 3.5319 no . . H26 H28C 3.0563 no . . Cl1 H2 2.2378 no . 1_655 Cl1 H2 3.1712 no . 2_555 Cl1 H4 3.3407 no . 1_455 Cl1 H4 3.0555 no . . Cl1 H5 2.7860 no . 1_455 Cl1 H7 2.7825 no . . Cl1 H13 3.1054 no . . Cl1 H15 2.6418 no . 2_555 Cl1 H15 3.1361 no . 2_655 Cl1 H16 3.1326 no . 2_655 Cl1 H19 3.0972 no . 1_655 Cl2 H1 2.2335 no . 1_455 Cl2 H1A 2.6776 no . 2_765 Cl2 H2A 3.2634 no . 2_665 Cl2 H5 3.3403 no . 1_455 Cl2 H18 3.5500 no . . Cl2 H18 3.2288 no . 1_655 Cl2 H19 2.8683 no . 1_655 Cl2 H20 3.6421 no . . O1 H1A 2.9851 no . 2_565 O1 H2A 2.6597 no . 2_565 O1 H18 2.4307 no . 1_455 O1 H20 3.1280 no . 1_455 O1 H23 2.9959 no . 1_355 O1 H24 3.5260 no . 1_355 N1 H1A 3.2436 no . 2_765 N2 H15 3.2131 no . 2_555 N2 H16 3.5371 no . 1_455 C1 H1 3.5280 no . 2_765 C1 H1A 3.3184 no . 2_765 C1 H6 3.6180 no . 1_655 C2 H1 3.6556 no . 1_455 C2 H6 3.6911 no . 1_655 C3 H1 3.3831 no . 1_455 C4 H1 3.6149 no . 1_455 C4 H7 3.3389 no . 1_655 C4 H13 3.5247 no . 1_655 C4 H19 3.1859 no . 1_655 C5 H7 3.2594 no . 1_655 C5 H18 3.5259 no . 1_655 C5 H19 3.0864 no . 1_655 C7 H4 3.6244 no . 1_455 C8 H4 3.5835 no . 1_455 C8 H14B 3.2358 no . 1_655 C9 H6 3.6058 no . 1_455 C9 H14B 2.8390 no . 1_655 C10 H6 3.6259 no . 1_455 C10 H14B 2.8809 no . 1_655 C11 H14B 3.3292 no . 1_655 C11 H28B 3.4931 no . 1_454 C12 H7 3.4365 no . 1_455 C12 H14B 3.6343 no . 1_655 C12 H16 3.5918 no . 2_555 C12 H27 3.0933 no . 2_655 C13 H4 3.3160 no . 1_455 C13 H7 3.4781 no . 1_455 C13 H14B 3.6252 no . 1_655 C13 H14C 3.6767 no . 1_655 C14 H28A 3.5619 no . 1_354 C14 H28B 3.0497 no . 1_354 C14 H28B 3.2408 no . 1_454 C14 H28C 3.3424 no . 1_354 C15 H2 3.3345 no . 2_555 C15 H13 3.3916 no . 2_555 C15 H15 3.5317 no . 2_555 C15 H16 3.6566 no . 1_455 C15 H21 3.6401 no . 1_455 C16 H2 3.2826 no . 1_655 C16 H12 3.4133 no . 2_555 C17 H2 3.3826 no . 1_655 C17 H19 3.4940 no . 1_655 C18 H5 2.9467 no . 1_455 C18 H19 3.6418 no . 1_655 C18 H20 3.3295 no . 1_455 C18 H23 3.4494 no . 1_455 C19 H4 3.4119 no . 1_455 C19 H5 2.8645 no . 1_455 C19 H20 3.2521 no . 1_455 C20 H19 3.3808 no . 1_655 C22 H28C 2.9060 no . 1_455 C23 H18 3.4509 no . 1_655 C23 H20 3.4536 no . 1_655 C23 H28C 2.8036 no . 1_455 C24 H14A 3.3491 no . 1_656 C24 H20 3.4414 no . 1_655 C24 H28C 2.8523 no . 1_455 C25 H14A 3.3537 no . 1_656 C25 H26 3.3460 no . 2_756 C25 H28C 3.0442 no . 1_455 C26 H14C 3.6485 no . 2_655 C26 H21 3.5345 no . 1_655 C26 H26 2.9627 no . 2_756 C26 H28A 3.1037 no . 2_756 C26 H28C 3.1057 no . 1_455 C27 H12 3.2391 no . 2_655 C27 H21 3.5827 no . 1_655 C27 H26 3.6983 no . 2_756 C27 H28A 2.9686 no . 2_756 C27 H28C 3.0394 no . 1_455 C28 H14A 3.1352 no . 1_656 C28 H14A 3.3564 no . 1_756 C28 H14B 3.4878 no . 1_756 C28 H14C 3.0975 no . 1_756 C28 H26 3.4674 no . 2_756 C28 H26 3.4310 no . 2_856 C28 H27 3.4660 no . 2_756 H1 Cl2 2.2335 no . 1_655 H1 C1 3.5280 no . 2_765 H1 C2 3.6556 no . 1_655 H1 C3 3.3831 no . 1_655 H1 C4 3.6149 no . 1_655 H1 H1A 3.0799 no . 2_765 H1A Cl2 2.6776 no . 2_765 H1A O1 2.9851 no . 2_565 H1A N1 3.2436 no . 2_765 H1A C1 3.3184 no . 2_765 H1A H1 3.0799 no . 2_765 H1A H1A 3.2012 no . 2_765 H1A H2A 3.6088 no . 1_655 H2 Cl1 2.2378 no . 1_455 H2 Cl1 3.1712 no . 2_555 H2 C15 3.3345 no . 2_555 H2 C16 3.2826 no . 1_455 H2 C17 3.3826 no . 1_455 H2 H4 3.5978 no . 1_455 H2 H15 2.8681 no . 2_555 H2 H16 3.3712 no . 1_455 H2A Cl2 3.2634 no . 2_665 H2A O1 2.6597 no . 2_565 H2A H1A 3.6088 no . 1_455 H2A Cl3B 3.5590 no . 2_565 H4 Cl1 3.0555 no . . H4 Cl1 3.3407 no . 1_655 H4 C7 3.6244 no . 1_655 H4 C8 3.5835 no . 1_655 H4 C13 3.3160 no . 1_655 H4 C19 3.4119 no . 1_655 H4 H2 3.5978 no . 1_655 H4 H5 3.6381 no . 1_455 H4 H7 3.4569 no . 1_655 H4 H13 3.0782 no . 1_655 H4 H15 3.2989 no . 2_655 H4 H19 2.9019 no . 1_655 H5 Cl1 2.7860 no . 1_655 H5 Cl2 3.3403 no . 1_655 H5 C18 2.9467 no . 1_655 H5 C19 2.8645 no . 1_655 H5 H4 3.6381 no . 1_655 H5 H7 3.3422 no . 1_655 H5 H18 2.8530 no . 1_655 H5 H19 2.6957 no . 1_655 H5 H19 3.1381 no . 1_755 H6 C1 3.6180 no . 1_455 H6 C2 3.6911 no . 1_455 H6 C9 3.6058 no . 1_655 H6 C10 3.6259 no . 1_655 H6 Cl3B 3.1665 no . 2_565 H7 Cl1 2.7825 no . . H7 C4 3.3389 no . 1_455 H7 C5 3.2594 no . 1_455 H7 C12 3.4365 no . 1_655 H7 C13 3.4781 no . 1_655 H7 H4 3.4569 no . 1_455 H7 H5 3.3422 no . 1_455 H7 H12 3.5522 no . 1_655 H7 H13 3.6102 no . 1_655 H7 H16 3.6443 no . 2_655 H9 H10 3.6880 no . 1_655 H9 H14B 3.1336 no . 1_655 H9 Cl3A 2.9946 no . 2_565 H9 O2 3.4870 no . 2_465 H9 Cl3B 3.3365 no . 2_565 H10 H9 3.6880 no . 1_455 H10 H14B 3.1828 no . 1_655 H10 Cl3A 3.5921 no . 1_554 H10 Cl3A 3.6921 no . 2_565 H10 O2 3.5688 no . 2_465 H12 C16 3.4133 no . 2_555 H12 C27 3.2391 no . 2_655 H12 H7 3.5522 no . 1_455 H12 H16 2.8424 no . 2_555 H12 H21 3.4177 no . 2_555 H12 H21 3.4983 no . 2_655 H12 H27 2.5159 no . 2_655 H13 Cl1 3.1054 no . . H13 C4 3.5247 no . 1_455 H13 C15 3.3916 no . 2_555 H13 H4 3.0782 no . 1_455 H13 H7 3.6102 no . 1_455 H13 H15 2.8748 no . 2_555 H13 H16 3.4929 no . 2_555 H13 H16 3.1217 no . 2_655 H13 H21 3.3403 no . 2_655 H14A C24 3.3491 no . 1_454 H14A C25 3.3537 no . 1_454 H14A C28 3.3564 no . 1_354 H14A C28 3.1352 no . 1_454 H14A H24 3.1204 no . 1_454 H14A H26 3.6558 no . 2_655 H14A H28A 3.5999 no . 1_354 H14A H28A 3.3042 no . 1_454 H14A H28B 3.0204 no . 1_354 H14A H28B 2.4520 no . 1_454 H14A H28C 2.9466 no . 1_354 H14B C8 3.2358 no . 1_455 H14B C9 2.8390 no . 1_455 H14B C10 2.8809 no . 1_455 H14B C11 3.3292 no . 1_455 H14B C12 3.6343 no . 1_455 H14B C13 3.6252 no . 1_455 H14B C28 3.4878 no . 1_354 H14B H9 3.1336 no . 1_455 H14B H10 3.1828 no . 1_455 H14B H28A 3.6569 no . 1_354 H14B H28B 2.7949 no . 1_354 H14B H28C 3.5223 no . 1_354 H14C C13 3.6767 no . 1_455 H14C C26 3.6485 no . 2_655 H14C C28 3.0975 no . 1_354 H14C H26 2.9847 no . 2_655 H14C H27 3.5565 no . 2_555 H14C H27 3.2795 no . 2_655 H14C H28A 2.9109 no . 1_354 H14C H28B 2.8175 no . 1_354 H14C H28B 3.5378 no . 1_454 H14C H28C 3.0390 no . 1_354 H15 Cl1 2.6418 no . 2_555 H15 Cl1 3.1361 no . 2_655 H15 N2 3.2131 no . 2_555 H15 C15 3.5317 no . 2_555 H15 H2 2.8681 no . 2_555 H15 H4 3.2989 no . 2_655 H15 H13 2.8748 no . 2_555 H15 H15 3.4334 no . 2_555 H15 H16 3.6013 no . 1_455 H16 Cl1 3.1326 no . 2_655 H16 N2 3.5371 no . 1_655 H16 C12 3.5918 no . 2_555 H16 C15 3.6566 no . 1_655 H16 H2 3.3712 no . 1_655 H16 H7 3.6443 no . 2_655 H16 H12 2.8424 no . 2_555 H16 H13 3.4929 no . 2_555 H16 H13 3.1217 no . 2_655 H16 H15 3.6013 no . 1_655 H18 Cl2 3.2288 no . 1_455 H18 Cl2 3.5500 no . . H18 O1 2.4307 no . 1_655 H18 C5 3.5259 no . 1_455 H18 C23 3.4509 no . 1_455 H18 H5 2.8530 no . 1_455 H18 H19 3.6194 no . 1_655 H18 H20 3.3782 no . 1_455 H18 H23 3.1024 no . 1_455 H19 Cl1 3.0972 no . 1_455 H19 Cl2 2.8683 no . 1_455 H19 C4 3.1859 no . 1_455 H19 C5 3.0864 no . 1_455 H19 C17 3.4940 no . 1_455 H19 C18 3.6418 no . 1_455 H19 C20 3.3808 no . 1_455 H19 H4 2.9019 no . 1_455 H19 H5 3.1381 no . 1_355 H19 H5 2.6957 no . 1_455 H19 H18 3.6194 no . 1_455 H19 H20 3.2398 no . 1_455 H20 Cl2 3.6421 no . . H20 O1 3.1280 no . 1_655 H20 C18 3.3295 no . 1_655 H20 C19 3.2521 no . 1_655 H20 C23 3.4536 no . 1_455 H20 C24 3.4414 no . 1_455 H20 H18 3.3782 no . 1_655 H20 H19 3.2398 no . 1_655 H20 H23 3.6392 no . 1_455 H20 H24 3.6373 no . 1_455 H21 C15 3.6401 no . 1_655 H21 C26 3.5345 no . 1_455 H21 C27 3.5827 no . 1_455 H21 H12 3.4177 no . 2_555 H21 H12 3.4983 no . 2_655 H21 H13 3.3403 no . 2_655 H21 H26 3.6879 no . 1_455 H23 O1 2.9959 no . 1_755 H23 C18 3.4494 no . 1_655 H23 H18 3.1024 no . 1_655 H23 H20 3.6392 no . 1_655 H23 H24 3.6932 no . 1_455 H23 H28C 3.2871 no . 1_455 H23 Cl3B 3.0316 no . 1_655 H24 O1 3.5260 no . 1_755 H24 H14A 3.1204 no . 1_656 H24 H20 3.6373 no . 1_655 H24 H23 3.6932 no . 1_655 H24 H28C 3.3375 no . 1_455 H24 Cl3A 3.5718 no . 1_655 H24 O2 3.0332 no . 1_755 H24 Cl3B 3.2877 no . 1_655 H26 C25 3.3460 no . 2_756 H26 C26 2.9627 no . 2_756 H26 C27 3.6983 no . 2_756 H26 C28 3.4674 no . 2_756 H26 C28 3.4310 no . 2_856 H26 H14A 3.6558 no . 2_655 H26 H14C 2.9847 no . 2_655 H26 H21 3.6879 no . 1_655 H26 H26 2.6790 no . 2_756 H26 H27 3.6306 no . 1_655 H26 H28A 2.8245 no . 2_756 H26 H28A 2.8865 no . 2_856 H26 H28C 3.0755 no . 2_856 H27 C12 3.0933 no . 2_655 H27 C28 3.4660 no . 2_756 H27 H12 2.5159 no . 2_655 H27 H14C 3.5565 no . 2_555 H27 H14C 3.2795 no . 2_655 H27 H26 3.6306 no . 1_455 H27 H28A 2.5645 no . 2_756 H27 H28B 3.6178 no . 2_756 H27 H28C 3.6139 no . 1_455 H28A C14 3.5619 no . 1_756 H28A C26 3.1037 no . 2_756 H28A C27 2.9686 no . 2_756 H28A H14A 3.3042 no . 1_656 H28A H14A 3.5999 no . 1_756 H28A H14B 3.6569 no . 1_756 H28A H14C 2.9109 no . 1_756 H28A H26 2.8245 no . 2_756 H28A H26 2.8865 no . 2_856 H28A H27 2.5645 no . 2_756 H28A H28A 3.3554 no . 2_856 H28A H28C 3.6222 no . 2_856 H28B C11 3.4931 no . 1_656 H28B C14 3.2408 no . 1_656 H28B C14 3.0497 no . 1_756 H28B H14A 2.4520 no . 1_656 H28B H14A 3.0204 no . 1_756 H28B H14B 2.7949 no . 1_756 H28B H14C 3.5378 no . 1_656 H28B H14C 2.8175 no . 1_756 H28B H27 3.6178 no . 2_756 H28C C14 3.3424 no . 1_756 H28C C22 2.9060 no . 1_655 H28C C23 2.8036 no . 1_655 H28C C24 2.8523 no . 1_655 H28C C25 3.0442 no . 1_655 H28C C26 3.1057 no . 1_655 H28C C27 3.0394 no . 1_655 H28C H14A 2.9466 no . 1_756 H28C H14B 3.5223 no . 1_756 H28C H14C 3.0390 no . 1_756 H28C H23 3.2871 no . 1_655 H28C H24 3.3375 no . 1_655 H28C H26 3.0755 no . 2_856 H28C H27 3.6139 no . 1_655 H28C H28A 3.6222 no . 2_856 Cl3A H9 2.9946 no . 2_565 Cl3A H10 3.5921 no . 1_556 Cl3A H10 3.6921 no . 2_565 Cl3A H24 3.5718 no . 1_455 O2 H9 3.4870 no . 2_465 O2 H10 3.5688 no . 2_465 O2 H24 3.0332 no . 1_355 Cl3B H2A 3.5590 no . 2_565 Cl3B H6 3.1665 no . 2_565 Cl3B H9 3.3365 no . 2_565 Cl3B H23 3.0316 no . 1_455 Cl3B H24 3.2877 no . 1_455 #============================================================================== loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_D _geom_hbond_site_symmetry_H _geom_hbond_site_symmetry_A _geom_hbond_distance_DA _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_angle_DHA _geom_hbond_publ_flag N1 H1 Cl2 . . 1_655 3.068(5) 0.880 2.233 158.2 no N2 H2 Cl1 . . 1_455 3.029(5) 0.880 2.238 149.5 no #============================================================================== # Additional structures and associated data_? identifiers # should be added at this point if there is more than one # structure analysis in the CIF. #============================================================================== # End of CIF #============================================================================== data_3-Br-SPHCl-2 _database_code_depnum_ccdc_archive 'CCDC 901989' #TrackingRef '2.cif' #============================================================================== # CHEMICAL DATA _chemical_formula_sum 'C13 H11 Br Cl N' _chemical_formula_moiety 'C13 H11 Br Cl N' _chemical_formula_weight 296.59 _chemical_melting_point ? #============================================================================== # CRYSTAL DATA _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/n 1' _symmetry_space_group_name_Hall '-P 2yn' _symmetry_Int_Tables_number 14 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 +X,+Y,+Z 2 1/2-X,1/2+Y,1/2-Z 3 -X,-Y,-Z 4 1/2+X,1/2-Y,1/2+Z #------------------------------------------------------------------------------ _cell_length_a 4.70335(13) _cell_length_b 32.1116(9) _cell_length_c 8.1926(3) _cell_angle_alpha 90.0000 _cell_angle_beta 98.0162(19) _cell_angle_gamma 90.0000 _cell_volume 1225.26(6) _cell_formula_units_Z 4 _cell_measurement_reflns_used 5246 _cell_measurement_theta_min 5.46 _cell_measurement_theta_max 68.22 _cell_measurement_temperature 123 #------------------------------------------------------------------------------ _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_max 0.400 _exptl_crystal_size_mid 0.070 _exptl_crystal_size_min 0.050 _exptl_crystal_density_diffrn 1.608 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 592.00 _exptl_absorpt_coefficient_mu 6.332 _exptl_absorpt_correction_type none #============================================================================== # EXPERIMENTAL DATA _diffrn_ambient_temperature 123 _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54187 _diffrn_measurement_device_type 'Rigaku R-AXIS RAPID' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.000 _diffrn_reflns_number 12303 _diffrn_reflns_av_R_equivalents 0.1167 _diffrn_reflns_theta_max 68.25 _diffrn_reflns_theta_full 68.25 _diffrn_measured_fraction_theta_max 0.994 _diffrn_measured_fraction_theta_full 0.994 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -38 _diffrn_reflns_limit_k_max 38 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_decay_% ? #============================================================================== # REFINEMENT DATA _refine_special_details ; Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F^2^. R-factor (gt) are based on F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 2230 _reflns_number_gt 1680 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0658 _refine_ls_wR_factor_ref 0.1743 _refine_ls_number_restraints 0 _refine_ls_hydrogen_treatment constr _refine_ls_number_reflns 2230 _refine_ls_number_parameters 145 _refine_ls_goodness_of_fit_ref 1.108 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0788P)^2^+1.0771P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_ls_shift/su_max 0.000 _refine_diff_density_max 0.840 _refine_diff_density_min -1.000 _refine_ls_extinction_method none _refine_ls_extinction_coef ? 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 for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; H H 0.0000 0.0000 ; International Tables for Crystallography (1992, Vol. C, Table 6.1.1.4) ; N N 0.0311 0.0180 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; Cl Cl 0.3639 0.7018 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; Br Br -0.6763 1.2805 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; #============================================================================== # ATOMIC COORDINATES AND THERMAL PARAMETERS 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 Br1 Br -0.09961(15) 0.185249(17) 1.42411(8) 0.0439(3) Uani 1.0 4 d . . . Cl1 Cl -0.5687(3) 0.04272(4) 1.26907(16) 0.0346(4) Uani 1.0 4 d . . . N1 N 1.1631(10) 0.03040(12) 0.7139(6) 0.0307(10) Uani 1.0 4 d . . . C1 C 1.0183(13) 0.05280(16) 0.5901(7) 0.0364(13) Uani 1.0 4 d . . . C2 C 0.8227(12) 0.08177(15) 0.6236(7) 0.0316(12) Uani 1.0 4 d . . . C3 C 0.7720(12) 0.08866(14) 0.7862(6) 0.0300(12) Uani 1.0 4 d . . . C4 C 0.9244(11) 0.06403(14) 0.9105(7) 0.0299(12) Uani 1.0 4 d . . . C5 C 1.1174(13) 0.03529(15) 0.8704(7) 0.0336(12) Uani 1.0 4 d . . . C6 C 0.5652(12) 0.12068(14) 0.8195(7) 0.0304(12) Uani 1.0 4 d . . . C7 C 0.4761(12) 0.12661(14) 0.9645(7) 0.0316(12) Uani 1.0 4 d . . . C8 C 0.2689(12) 0.15782(14) 1.0044(7) 0.0315(12) Uani 1.0 4 d . . . C9 C 0.1566(14) 0.18894(14) 0.8950(8) 0.0349(13) Uani 1.0 4 d . . . C10 C -0.0381(12) 0.21787(15) 0.9409(7) 0.0362(13) Uani 1.0 4 d . . . C11 C -0.1171(12) 0.21694(14) 1.0979(7) 0.0361(13) Uani 1.0 4 d . . . C12 C 0.0025(13) 0.18658(14) 1.2074(7) 0.0311(13) Uani 1.0 4 d . . . C13 C 0.1896(12) 0.15694(14) 1.1619(7) 0.0348(13) Uani 1.0 4 d . . . H1 H 1.2911 0.0121 0.6912 0.0368 Uiso 1.0 4 calc R . . H1A H 1.0526 0.0484 0.4798 0.0437 Uiso 1.0 4 calc R . . H2 H 0.7198 0.0974 0.5362 0.0379 Uiso 1.0 4 calc R . . H4 H 0.8935 0.0673 1.0219 0.0359 Uiso 1.0 4 calc R . . H5 H 1.2202 0.0186 0.9544 0.0403 Uiso 1.0 4 calc R . . H6 H 0.4898 0.1384 0.7311 0.0365 Uiso 1.0 4 calc R . . H7 H 0.5548 0.1087 1.0516 0.0379 Uiso 1.0 4 calc R . . H9 H 0.2134 0.1904 0.7883 0.0419 Uiso 1.0 4 calc R . . H10 H -0.1174 0.2384 0.8643 0.0434 Uiso 1.0 4 calc R . . H11 H -0.2499 0.2366 1.1297 0.0434 Uiso 1.0 4 calc R . . H13 H 0.2640 0.1360 1.2379 0.0417 Uiso 1.0 4 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_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 Br1 0.0594(6) 0.0374(4) 0.0369(5) 0.0016(3) 0.0135(4) -0.0042(3) Cl1 0.0457(9) 0.0310(7) 0.0273(7) 0.0043(6) 0.0055(6) -0.0003(5) N1 0.035(3) 0.025(2) 0.033(3) 0.0007(18) 0.010(2) -0.0050(18) C1 0.051(4) 0.032(3) 0.028(3) -0.010(3) 0.012(3) -0.004(3) C2 0.036(3) 0.032(3) 0.025(3) 0.001(3) 0.002(3) 0.002(3) C3 0.041(3) 0.022(3) 0.028(3) -0.005(2) 0.007(3) -0.001(2) C4 0.033(3) 0.026(3) 0.031(3) -0.003(2) 0.007(3) -0.003(2) C5 0.042(4) 0.030(3) 0.027(3) -0.004(3) 0.001(3) 0.004(3) C6 0.039(3) 0.023(3) 0.028(3) -0.003(3) -0.000(3) 0.000(2) C7 0.039(3) 0.023(3) 0.031(3) -0.003(3) 0.001(3) 0.000(2) C8 0.035(3) 0.024(3) 0.034(3) -0.004(2) 0.001(3) -0.000(3) C9 0.045(4) 0.033(3) 0.028(4) -0.003(3) 0.008(3) -0.001(3) C10 0.043(4) 0.024(3) 0.042(4) 0.002(3) 0.008(3) 0.008(3) C11 0.040(4) 0.021(3) 0.048(4) 0.003(3) 0.007(3) -0.004(3) C12 0.034(3) 0.026(3) 0.034(4) -0.004(2) 0.006(3) -0.005(2) C13 0.042(4) 0.021(3) 0.040(4) -0.002(3) 0.003(3) -0.000(3) #============================================================================== _computing_data_collection 'RAPID AUTO (Rigaku, ????)' _computing_cell_refinement 'RAPID AUTO' _computing_data_reduction 'RAPID AUTO' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_publication_material 'CrystalStructure 4.0 (Rigaku, 2010)' _computing_molecular_graphics 'CrystalStructure 4.0' #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 Br1 C12 1.903(6) yes . . N1 C1 1.348(7) yes . . N1 C5 1.338(7) yes . . C1 C2 1.363(8) yes . . C2 C3 1.404(8) yes . . C3 C4 1.404(7) yes . . C3 C6 1.467(8) yes . . C4 C5 1.366(8) yes . . C6 C7 1.327(8) yes . . C7 C8 1.466(8) yes . . C8 C9 1.396(7) yes . . C8 C13 1.392(9) yes . . C9 C10 1.392(8) yes . . C10 C11 1.388(9) yes . . C11 C12 1.390(7) yes . . C12 C13 1.382(8) yes . . N1 H1 0.880 no . . C1 H1A 0.950 no . . C2 H2 0.950 no . . C4 H4 0.950 no . . C5 H5 0.950 no . . C6 H6 0.950 no . . C7 H7 0.950 no . . C9 H9 0.950 no . . C10 H10 0.950 no . . C11 H11 0.950 no . . C13 H13 0.950 no . . 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 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 C1 N1 C5 121.8(5) yes . . . N1 C1 C2 119.8(5) yes . . . C1 C2 C3 120.5(5) yes . . . C2 C3 C4 117.5(5) yes . . . C2 C3 C6 119.4(5) yes . . . C4 C3 C6 123.0(5) yes . . . C3 C4 C5 119.7(5) yes . . . N1 C5 C4 120.7(5) yes . . . C3 C6 C7 124.5(5) yes . . . C6 C7 C8 126.9(5) yes . . . C7 C8 C9 123.3(6) yes . . . C7 C8 C13 117.7(5) yes . . . C9 C8 C13 118.9(5) yes . . . C8 C9 C10 120.5(6) yes . . . C9 C10 C11 120.5(5) yes . . . C10 C11 C12 118.5(5) yes . . . Br1 C12 C11 119.1(5) yes . . . Br1 C12 C13 119.3(4) yes . . . C11 C12 C13 121.6(6) yes . . . C8 C13 C12 119.9(5) yes . . . C1 N1 H1 119.115 no . . . C5 N1 H1 119.119 no . . . N1 C1 H1A 120.115 no . . . C2 C1 H1A 120.090 no . . . C1 C2 H2 119.757 no . . . C3 C2 H2 119.749 no . . . C3 C4 H4 120.177 no . . . C5 C4 H4 120.167 no . . . N1 C5 H5 119.643 no . . . C4 C5 H5 119.645 no . . . C3 C6 H6 117.729 no . . . C7 C6 H6 117.725 no . . . C6 C7 H7 116.542 no . . . C8 C7 H7 116.552 no . . . C8 C9 H9 119.730 no . . . C10 C9 H9 119.727 no . . . C9 C10 H10 119.763 no . . . C11 C10 H10 119.764 no . . . C10 C11 H11 120.769 no . . . C12 C11 H11 120.763 no . . . C8 C13 H13 120.034 no . . . C12 C13 H13 120.042 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 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 C1 N1 C5 C4 -1.3(8) no . . . . C5 N1 C1 C2 1.0(8) no . . . . N1 C1 C2 C3 0.4(8) no . . . . C1 C2 C3 C4 -1.5(8) no . . . . C1 C2 C3 C6 178.6(5) no . . . . C2 C3 C4 C5 1.3(7) no . . . . C2 C3 C6 C7 171.9(5) no . . . . C4 C3 C6 C7 -8.0(8) no . . . . C6 C3 C4 C5 -178.9(4) no . . . . C3 C4 C5 N1 0.1(8) no . . . . C3 C6 C7 C8 -179.5(4) no . . . . C6 C7 C8 C9 -6.7(8) no . . . . C6 C7 C8 C13 175.6(5) no . . . . C7 C8 C9 C10 -179.5(5) no . . . . C7 C8 C13 C12 177.8(4) no . . . . C9 C8 C13 C12 0.0(7) no . . . . C13 C8 C9 C10 -1.9(8) no . . . . C8 C9 C10 C11 1.9(8) no . . . . C9 C10 C11 C12 0.0(8) no . . . . C10 C11 C12 Br1 179.2(4) no . . . . C10 C11 C12 C13 -1.9(8) no . . . . Br1 C12 C13 C8 -179.2(3) no . . . . C11 C12 C13 C8 1.9(8) no . . . . loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_publ_flag _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 N1 C3 2.746(7) no . . C1 C4 2.746(8) no . . C2 C5 2.731(7) no . . C4 C7 2.990(8) no . . C6 C9 3.035(8) no . . C8 C11 2.806(8) no . . C9 C12 2.756(9) no . . C10 C13 2.777(7) no . . Cl1 N1 3.016(5) no . 3_657 Cl1 C1 3.495(7) no . 1_356 Cl1 C1 3.552(6) no . 1_456 Cl1 C2 3.450(5) no . 1_456 Cl1 C4 3.581(5) no . 1_355 Cl1 C5 3.400(6) no . 1_355 Cl1 C5 3.573(6) no . 3_657 N1 Cl1 3.016(5) no . 3_657 N1 C3 3.403(7) no . 1_655 N1 C6 3.503(7) no . 1_655 C1 Cl1 3.552(6) no . 1_654 C1 Cl1 3.495(7) no . 1_754 C2 Cl1 3.450(5) no . 1_654 C3 N1 3.403(7) no . 1_455 C3 C8 3.525(7) no . 1_655 C4 Cl1 3.581(5) no . 1_755 C4 C7 3.263(7) no . 1_655 C4 C8 3.455(7) no . 1_655 C5 Cl1 3.400(6) no . 1_755 C5 Cl1 3.573(6) no . 3_657 C5 C5 3.395(8) no . 3_757 C5 C6 3.517(8) no . 1_655 C5 C7 3.417(7) no . 1_655 C6 N1 3.503(7) no . 1_455 C6 C5 3.517(8) no . 1_455 C6 C9 3.528(8) no . 1_655 C7 C4 3.263(7) no . 1_455 C7 C5 3.417(7) no . 1_455 C7 C11 3.562(7) no . 1_655 C7 C12 3.525(7) no . 1_655 C8 C3 3.525(7) no . 1_455 C8 C4 3.455(7) no . 1_455 C8 C11 3.452(8) no . 1_655 C9 C6 3.528(8) no . 1_455 C11 C7 3.562(7) no . 1_455 C11 C8 3.452(8) no . 1_455 C12 C7 3.525(7) no . 1_455 Br1 H11 2.9256 no . . Br1 H13 2.9121 no . . N1 H2 3.2018 no . . N1 H4 3.2054 no . . C1 H5 3.1981 no . . C2 H1 3.1352 no . . C2 H4 3.2671 no . . C2 H6 2.6307 no . . C3 H1A 3.2616 no . . C3 H5 3.2548 no . . C3 H7 2.6084 no . . C4 H1 3.1384 no . . C4 H2 3.2646 no . . C4 H6 3.3476 no . . C4 H7 2.6416 no . . C5 H1A 3.1995 no . . C6 H2 2.6354 no . . C6 H4 2.7122 no . . C6 H9 2.7740 no . . C7 H4 2.7281 no . . C7 H9 2.7029 no . . C7 H13 2.5939 no . . C8 H6 2.6705 no . . C8 H10 3.2758 no . . C9 H6 2.7348 no . . C9 H7 3.3344 no . . C9 H11 3.2742 no . . C9 H13 3.2625 no . . C11 H9 3.2672 no . . C11 H13 3.2730 no . . C12 H10 3.2475 no . . C13 H7 2.5684 no . . C13 H9 3.2599 no . . C13 H11 3.2763 no . . H1 H1A 2.2537 no . . H1 H5 2.2371 no . . H1A H2 2.3108 no . . H2 H6 2.4364 no . . H4 H5 2.3137 no . . H4 H7 2.1146 no . . H6 H7 2.7698 no . . H6 H9 2.2058 no . . H7 H13 2.3561 no . . H9 H10 2.3352 no . . H10 H11 2.3453 no . . Br1 H2 3.1206 no . 1_456 Br1 H9 3.1423 no . 1_556 Br1 H10 3.4424 no . 4_455 Br1 H10 3.4217 no . 4_555 Br1 H11 3.3269 no . 4_555 Br1 H13 3.5376 no . 1_455 Cl1 H1 2.1883 no . 3_657 Cl1 H1A 2.6539 no . 1_356 Cl1 H1A 3.1855 no . 1_456 Cl1 H2 2.9810 no . 1_456 Cl1 H4 3.1134 no . 1_355 Cl1 H4 3.2679 no . 1_455 Cl1 H5 2.7416 no . 1_355 Cl1 H5 3.2793 no . 3_657 Cl1 H7 2.8800 no . 1_455 Cl1 H13 3.0981 no . 1_455 N1 H1A 3.0830 no . 3_756 C1 H1 3.2912 no . 3_756 C1 H1A 3.3091 no . 3_756 C2 H1 3.4576 no . 1_455 C3 H1 3.3587 no . 1_455 C4 H5 2.9896 no . 3_757 C4 H7 3.3514 no . 1_655 C5 H4 3.4137 no . 3_757 C5 H5 2.8658 no . 3_757 C5 H7 3.3387 no . 1_655 C7 H4 3.4223 no . 1_455 C8 H4 3.4134 no . 1_455 C8 H11 3.4537 no . 1_655 C9 H11 3.5123 no . 1_655 C9 H11 3.3015 no . 4_554 C10 H11 3.3820 no . 4_554 C11 H9 3.5032 no . 4_455 C11 H10 3.3036 no . 4_555 C12 H7 3.4004 no . 1_455 C12 H10 3.1642 no . 4_555 C13 H4 3.3300 no . 1_455 C13 H7 3.3725 no . 1_455 H1 Cl1 2.1883 no . 3_657 H1 C1 3.2912 no . 3_756 H1 C2 3.4576 no . 1_655 H1 C3 3.3587 no . 1_655 H1 H1A 2.7780 no . 3_756 H1 H5 3.5805 no . 3_857 H1A Cl1 3.1855 no . 1_654 H1A Cl1 2.6539 no . 1_754 H1A N1 3.0830 no . 3_756 H1A C1 3.3091 no . 3_756 H1A H1 2.7780 no . 3_756 H1A H1A 3.1734 no . 3_756 H1A H2 3.4830 no . 1_655 H2 Br1 3.1206 no . 1_654 H2 Cl1 2.9810 no . 1_654 H2 H1A 3.4830 no . 1_455 H2 H13 3.2618 no . 1_554 H4 Cl1 3.2679 no . 1_655 H4 Cl1 3.1134 no . 1_755 H4 C5 3.4137 no . 3_757 H4 C7 3.4223 no . 1_655 H4 C8 3.4134 no . 1_655 H4 C13 3.3300 no . 1_655 H4 H5 3.5062 no . 1_455 H4 H5 2.8225 no . 3_757 H4 H7 3.3602 no . 1_655 H4 H13 3.1889 no . 1_655 H5 Cl1 2.7416 no . 1_755 H5 Cl1 3.2793 no . 3_657 H5 C4 2.9896 no . 3_757 H5 C5 2.8658 no . 3_757 H5 H1 3.5805 no . 3_857 H5 H4 3.5062 no . 1_655 H5 H4 2.8225 no . 3_757 H5 H5 2.5900 no . 3_757 H5 H5 2.8917 no . 3_857 H5 H7 3.3373 no . 1_655 H7 Cl1 2.8800 no . 1_655 H7 C4 3.3514 no . 1_455 H7 C5 3.3387 no . 1_455 H7 C12 3.4004 no . 1_655 H7 C13 3.3725 no . 1_655 H7 H4 3.3602 no . 1_455 H7 H5 3.3373 no . 1_455 H7 H13 3.5779 no . 1_655 H9 Br1 3.1423 no . 1_554 H9 C11 3.5032 no . 4_554 H9 H10 3.4819 no . 1_655 H9 H11 2.6976 no . 4_554 H10 Br1 3.4217 no . 4_454 H10 Br1 3.4424 no . 4_554 H10 C11 3.3036 no . 4_454 H10 C12 3.1642 no . 4_454 H10 H9 3.4819 no . 1_455 H10 H11 3.4049 no . 4_454 H10 H11 2.8722 no . 4_554 H11 Br1 3.3269 no . 4_454 H11 C8 3.4537 no . 1_455 H11 C9 3.5123 no . 1_455 H11 C9 3.3015 no . 4_455 H11 C10 3.3820 no . 4_455 H11 H9 2.6976 no . 4_455 H11 H10 2.8722 no . 4_455 H11 H10 3.4049 no . 4_555 H13 Br1 3.5376 no . 1_655 H13 Cl1 3.0981 no . 1_655 H13 H2 3.2618 no . 1_556 H13 H4 3.1889 no . 1_455 H13 H7 3.5779 no . 1_455 #============================================================================== loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_D _geom_hbond_site_symmetry_H _geom_hbond_site_symmetry_A _geom_hbond_distance_DA _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_angle_DHA _geom_hbond_publ_flag N1 H1 Cl1 . . 3_657 3.016(5) 0.880 2.188 156.6 no data_3-NO2-SP-HCl _database_code_depnum_ccdc_archive 'CCDC 901990' #TrackingRef '3.cif' #============================================================================== # CHEMICAL DATA _chemical_formula_sum 'C13 H11 Cl N2 O2' _chemical_formula_moiety 'C13 H11 Cl N2 O2' _chemical_formula_weight 262.70 _chemical_melting_point ? _chemical_absolute_configuration ? #============================================================================== # CRYSTAL DATA _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P 1' _symmetry_space_group_name_Hall 'P 1' _symmetry_Int_Tables_number 1 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 +X,+Y,+Z #------------------------------------------------------------------------------ _cell_length_a 4.79000(10) _cell_length_b 8.28058(17) _cell_length_c 16.2189(4) _cell_angle_alpha 105.8270(14) _cell_angle_beta 91.5910(13) _cell_angle_gamma 98.6340(14) _cell_volume 610.30(3) _cell_formula_units_Z 2 _cell_measurement_reflns_used 3822 _cell_measurement_theta_min 5.55 _cell_measurement_theta_max 68.05 _cell_measurement_temperature 123 #------------------------------------------------------------------------------ _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_max 0.350 _exptl_crystal_size_mid 0.250 _exptl_crystal_size_min 0.250 _exptl_crystal_density_diffrn 1.429 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 272.00 _exptl_absorpt_coefficient_mu 2.744 _exptl_absorpt_correction_type none #============================================================================== # EXPERIMENTAL DATA _diffrn_ambient_temperature 123 _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54187 _diffrn_measurement_device_type 'Rigaku R-AXIS RAPID' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.000 _diffrn_reflns_number 6630 _diffrn_reflns_av_R_equivalents 0.0488 _diffrn_reflns_theta_max 68.16 _diffrn_reflns_theta_full 68.16 _diffrn_measured_fraction_theta_max 0.980 _diffrn_measured_fraction_theta_full 0.980 _diffrn_reflns_limit_h_min -5 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_decay_% ? #============================================================================== # REFINEMENT DATA _refine_special_details ; Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F^2^. R-factor (gt) are based on F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 3636 _reflns_number_gt 3273 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0449 _refine_ls_wR_factor_ref 0.1981 _refine_ls_number_restraints 3 _refine_ls_hydrogen_treatment constr _refine_ls_number_reflns 3636 _refine_ls_number_parameters 325 _refine_ls_goodness_of_fit_ref 1.206 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.1318P)^2^+0.2391P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_ls_shift/su_max 0.007 _refine_diff_density_max 0.460 _refine_diff_density_min -0.410 _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack, H. D. (1983), Acta Cryst. A39, 876-881. 1441 Friedel Pairs' _refine_ls_abs_structure_Flack 0.16(4) 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 for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; H H 0.0000 0.0000 ; International Tables for Crystallography (1992, Vol. C, Table 6.1.1.4) ; O O 0.0492 0.0322 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; N N 0.0311 0.0180 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; Cl Cl 0.3639 0.7018 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; #============================================================================== # ATOMIC COORDINATES AND THERMAL PARAMETERS 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 0.6713(3) 0.07209(13) 0.23163(8) 0.0305(4) Uani 1.0 1 d . . . Cl2 Cl 0.4800(3) 0.53004(13) 1.06300(8) 0.0303(4) Uani 1.0 1 d . . . O1 O 1.0002(13) -0.0136(7) 0.4785(4) 0.0413(14) Uani 1.0 1 d . . . O2 O 1.3883(14) 0.0948(8) 0.5566(4) 0.0455(16) Uani 1.0 1 d . . . O3 O -0.2246(14) 0.5102(8) 0.7381(4) 0.0462(16) Uani 1.0 1 d . . . O4 O 0.1644(15) 0.6131(7) 0.8187(4) 0.0564(19) Uani 1.0 1 d . . . N1 N -0.0773(13) 0.6239(8) 0.2103(4) 0.0264(14) Uani 1.0 1 d . . . N2 N 1.1766(14) 0.1098(8) 0.5189(4) 0.0303(15) Uani 1.0 1 d . . . N3 N 1.2220(14) -0.0300(8) 1.0819(4) 0.0295(14) Uani 1.0 1 d . . . N4 N -0.0106(16) 0.4947(8) 0.7780(4) 0.0356(16) Uani 1.0 1 d . . . C1 C 0.0873(18) 0.7747(10) 0.2607(5) 0.0341(18) Uani 1.0 1 d . . . C2 C 0.2899(19) 0.7613(10) 0.3179(5) 0.038(2) Uani 1.0 1 d . . . C3 C 0.3384(16) 0.6113(10) 0.3278(5) 0.0291(16) Uani 1.0 1 d . . . C4 C 0.1742(15) 0.4615(10) 0.2760(5) 0.0259(16) Uani 1.0 1 d . . . C5 C -0.0317(15) 0.4752(10) 0.2178(5) 0.0261(15) Uani 1.0 1 d . . . C6 C 0.5581(17) 0.6077(11) 0.3925(5) 0.0351(19) Uani 1.0 1 d . . . C7 C 0.6468(16) 0.4698(9) 0.3999(5) 0.0287(16) Uani 1.0 1 d . . . C8 C 0.8591(16) 0.4572(9) 0.4638(5) 0.0262(15) Uani 1.0 1 d . . . C9 C 1.0200(17) 0.5998(10) 0.5265(5) 0.0325(17) Uani 1.0 1 d . . . C10 C 1.215(2) 0.5810(10) 0.5830(6) 0.0339(18) Uani 1.0 1 d . . . C11 C 1.2792(17) 0.4185(10) 0.5814(5) 0.0319(17) Uani 1.0 1 d . . . C12 C 1.1226(17) 0.2813(9) 0.5206(5) 0.0278(16) Uani 1.0 1 d . . . C13 C 0.9183(16) 0.2939(9) 0.4616(5) 0.0271(16) Uani 1.0 1 d . . . C14 C 1.0732(17) -0.1667(10) 1.0358(5) 0.0308(17) Uani 1.0 1 d . . . C15 C 0.8632(15) -0.1662(9) 0.9758(5) 0.0262(16) Uani 1.0 1 d . . . C16 C 0.8170(15) -0.0044(9) 0.9664(5) 0.0234(14) Uani 1.0 1 d . . . C17 C 0.9876(16) 0.1402(9) 1.0196(5) 0.0287(16) Uani 1.0 1 d . . . C18 C 1.1856(17) 0.1281(10) 1.0760(5) 0.0313(17) Uani 1.0 1 d . . . C19 C 0.5985(15) -0.0049(9) 0.9010(5) 0.0245(15) Uani 1.0 1 d . . . C20 C 0.5142(18) 0.1368(10) 0.8942(5) 0.0307(16) Uani 1.0 1 d . . . C21 C 0.2897(18) 0.1444(11) 0.8300(5) 0.0312(17) Uani 1.0 1 d . . . C22 C 0.1429(17) 0.0039(10) 0.7701(5) 0.0304(17) Uani 1.0 1 d . . . C23 C -0.0680(18) 0.0254(10) 0.7111(5) 0.0287(16) Uani 1.0 1 d . . . C24 C -0.1174(17) 0.1848(9) 0.7137(5) 0.0260(15) Uani 1.0 1 d . . . C25 C 0.0395(15) 0.3216(10) 0.7744(5) 0.0290(16) Uani 1.0 1 d . . . C26 C 0.2391(15) 0.3023(10) 0.8323(5) 0.0289(16) Uani 1.0 1 d . . . H1 H -0.2122 0.6283 0.1735 0.0317 Uiso 1.0 1 calc R . . H1A H 0.0588 0.8824 0.2551 0.0409 Uiso 1.0 1 calc R . . H2 H 0.4027 0.8628 0.3526 0.0454 Uiso 1.0 1 calc R . . H3 H 1.3539 -0.0367 1.1191 0.0354 Uiso 1.0 1 calc R . . H4 H 0.2034 0.3534 0.2807 0.0311 Uiso 1.0 1 calc R . . H5 H -0.1433 0.3744 0.1821 0.0313 Uiso 1.0 1 calc R . . H6 H 0.6413 0.7131 0.4317 0.0421 Uiso 1.0 1 calc R . . H7 H 0.5642 0.3662 0.3593 0.0344 Uiso 1.0 1 calc R . . H9 H 0.9883 0.7112 0.5282 0.0390 Uiso 1.0 1 calc R . . H10 H 1.3111 0.6788 0.6250 0.0407 Uiso 1.0 1 calc R . . H11 H 1.4213 0.4047 0.6198 0.0383 Uiso 1.0 1 calc R . . H13 H 0.8202 0.1952 0.4206 0.0325 Uiso 1.0 1 calc R . . H14 H 1.1073 -0.2724 1.0429 0.0369 Uiso 1.0 1 calc R . . H15 H 0.7530 -0.2693 0.9419 0.0314 Uiso 1.0 1 calc R . . H17 H 0.9621 0.2494 1.0155 0.0344 Uiso 1.0 1 calc R . . H18 H 1.3001 0.2276 1.1117 0.0375 Uiso 1.0 1 calc R . . H19 H 0.5144 -0.1104 0.8622 0.0294 Uiso 1.0 1 calc R . . H20 H 0.6030 0.2412 0.9331 0.0369 Uiso 1.0 1 calc R . . H22 H 0.1808 -0.1066 0.7678 0.0364 Uiso 1.0 1 calc R . . H23 H -0.1731 -0.0711 0.6703 0.0344 Uiso 1.0 1 calc R . . H24 H -0.2555 0.2012 0.6749 0.0312 Uiso 1.0 1 calc R . . H26 H 0.3410 0.3993 0.8736 0.0347 Uiso 1.0 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_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 Cl1 0.0345(9) 0.0248(8) 0.0325(8) 0.0024(6) -0.0028(7) 0.0102(6) Cl2 0.0316(9) 0.0288(9) 0.0317(8) 0.0037(6) -0.0022(7) 0.0117(7) O1 0.047(4) 0.039(3) 0.041(3) 0.015(3) -0.016(3) 0.016(3) O2 0.043(4) 0.047(4) 0.056(4) 0.020(3) -0.006(3) 0.024(3) O3 0.052(5) 0.037(4) 0.050(4) 0.008(3) -0.010(4) 0.012(3) O4 0.063(5) 0.022(3) 0.069(5) -0.014(3) -0.005(4) 0.000(3) N1 0.023(4) 0.044(4) 0.019(3) 0.010(3) 0.005(3) 0.017(3) N2 0.028(4) 0.027(3) 0.028(3) -0.004(3) -0.005(3) 0.000(3) N3 0.025(4) 0.030(4) 0.038(4) 0.009(3) 0.002(3) 0.014(3) N4 0.049(4) 0.033(4) 0.033(4) 0.016(3) 0.015(3) 0.017(3) C1 0.039(5) 0.034(4) 0.035(5) 0.013(3) 0.017(4) 0.016(4) C2 0.046(5) 0.035(5) 0.028(4) 0.001(4) 0.011(4) 0.005(3) C3 0.026(4) 0.040(4) 0.022(4) 0.008(3) 0.009(3) 0.008(3) C4 0.025(4) 0.036(4) 0.025(4) 0.016(3) 0.008(3) 0.016(3) C5 0.025(4) 0.030(4) 0.026(4) 0.003(3) 0.004(3) 0.013(3) C6 0.035(5) 0.042(5) 0.029(4) 0.010(4) 0.018(3) 0.009(4) C7 0.028(4) 0.026(4) 0.027(4) -0.001(3) 0.007(3) -0.000(3) C8 0.024(4) 0.030(4) 0.025(4) 0.003(3) 0.007(3) 0.009(3) C9 0.040(5) 0.034(4) 0.033(4) 0.013(4) 0.013(4) 0.020(3) C10 0.042(5) 0.027(4) 0.031(4) 0.003(3) 0.008(4) 0.004(3) C11 0.028(4) 0.038(5) 0.029(4) 0.004(4) 0.004(4) 0.009(4) C12 0.043(5) 0.021(4) 0.020(4) 0.007(3) 0.008(3) 0.006(3) C13 0.029(4) 0.019(3) 0.032(4) 0.004(3) 0.007(3) 0.003(3) C14 0.031(4) 0.029(4) 0.041(5) 0.016(3) 0.003(4) 0.019(4) C15 0.024(4) 0.021(4) 0.037(4) 0.006(3) 0.002(3) 0.012(3) C16 0.019(4) 0.031(4) 0.025(4) 0.005(3) 0.004(3) 0.016(3) C17 0.031(4) 0.028(4) 0.031(4) 0.004(3) 0.004(4) 0.015(3) C18 0.030(5) 0.033(4) 0.029(4) 0.002(3) 0.005(3) 0.007(3) C19 0.022(4) 0.017(4) 0.032(4) -0.001(3) -0.006(3) 0.005(3) C20 0.036(5) 0.034(4) 0.026(4) 0.007(3) 0.006(3) 0.013(3) C21 0.026(4) 0.044(5) 0.028(4) 0.009(4) 0.006(3) 0.015(3) C22 0.037(5) 0.029(4) 0.027(4) 0.012(3) 0.007(3) 0.008(3) C23 0.029(4) 0.031(4) 0.022(4) 0.003(3) -0.003(3) 0.004(3) C24 0.032(4) 0.031(4) 0.022(4) 0.011(3) 0.003(3) 0.015(3) C25 0.019(4) 0.035(4) 0.035(4) 0.004(3) 0.006(3) 0.013(3) C26 0.021(4) 0.042(4) 0.022(4) -0.003(3) -0.005(3) 0.012(3) #============================================================================== _computing_data_collection 'RAPID AUTO (Rigaku, ????)' _computing_cell_refinement 'RAPID AUTO' _computing_data_reduction 'RAPID AUTO' _computing_structure_solution 'SIR92 (Altomare, et al., 1994)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_publication_material 'CrystalStructure 4.0 (Rigaku, 2010)' _computing_molecular_graphics 'CrystalStructure 4.0' #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 O1 N2 1.238(8) yes . . O2 N2 1.209(10) yes . . O3 N4 1.239(11) yes . . O4 N4 1.212(8) yes . . N1 C1 1.400(9) yes . . N1 C5 1.318(11) yes . . N2 C12 1.474(11) yes . . N3 C14 1.271(9) yes . . N3 C18 1.374(12) yes . . N4 C25 1.474(11) yes . . C1 C2 1.362(13) yes . . C2 C3 1.348(13) yes . . C3 C4 1.402(9) yes . . C3 C6 1.474(12) yes . . C4 C5 1.385(11) yes . . C6 C7 1.310(13) yes . . C7 C8 1.467(11) yes . . C8 C9 1.432(10) yes . . C8 C13 1.414(11) yes . . C9 C10 1.344(13) yes . . C10 C11 1.419(13) yes . . C11 C12 1.385(9) yes . . C12 C13 1.384(11) yes . . C14 C15 1.382(11) yes . . C15 C16 1.437(11) yes . . C16 C17 1.396(9) yes . . C16 C19 1.467(11) yes . . C17 C18 1.333(12) yes . . C19 C20 1.327(12) yes . . C20 C21 1.496(12) yes . . C21 C22 1.376(10) yes . . C21 C26 1.356(13) yes . . C22 C23 1.436(12) yes . . C23 C24 1.365(12) yes . . C24 C25 1.383(9) yes . . C25 C26 1.378(11) yes . . N1 H1 0.880 no . . N3 H3 0.880 no . . C1 H1A 0.950 no . . C2 H2 0.950 no . . C4 H4 0.950 no . . C5 H5 0.950 no . . C6 H6 0.950 no . . C7 H7 0.950 no . . C9 H9 0.950 no . . C10 H10 0.950 no . . C11 H11 0.950 no . . C13 H13 0.950 no . . C14 H14 0.950 no . . C15 H15 0.950 no . . C17 H17 0.950 no . . C18 H18 0.950 no . . C19 H19 0.950 no . . C20 H20 0.950 no . . C22 H22 0.950 no . . C23 H23 0.950 no . . C24 H24 0.950 no . . C26 H26 0.950 no . . 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 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 C1 N1 C5 120.5(7) yes . . . O1 N2 O2 122.8(7) yes . . . O1 N2 C12 117.8(7) yes . . . O2 N2 C12 119.4(6) yes . . . C14 N3 C18 122.7(8) yes . . . O3 N4 O4 124.1(8) yes . . . O3 N4 C25 118.3(6) yes . . . O4 N4 C25 117.6(7) yes . . . N1 C1 C2 117.5(8) yes . . . C1 C2 C3 123.3(7) yes . . . C2 C3 C4 118.4(8) yes . . . C2 C3 C6 120.0(7) yes . . . C4 C3 C6 121.7(8) yes . . . C3 C4 C5 118.4(8) yes . . . N1 C5 C4 122.0(6) yes . . . C3 C6 C7 124.7(7) yes . . . C6 C7 C8 127.4(6) yes . . . C7 C8 C9 124.5(8) yes . . . C7 C8 C13 118.1(6) yes . . . C9 C8 C13 117.4(8) yes . . . C8 C9 C10 122.0(8) yes . . . C9 C10 C11 121.5(7) yes . . . C10 C11 C12 116.0(8) yes . . . N2 C12 C11 117.6(7) yes . . . N2 C12 C13 117.8(6) yes . . . C11 C12 C13 124.6(8) yes . . . C8 C13 C12 118.5(6) yes . . . N3 C14 C15 121.9(8) yes . . . C14 C15 C16 117.8(6) yes . . . C15 C16 C17 116.9(7) yes . . . C15 C16 C19 117.5(6) yes . . . C17 C16 C19 125.5(7) yes . . . C16 C17 C18 121.4(8) yes . . . N3 C18 C17 119.3(7) yes . . . C16 C19 C20 122.4(6) yes . . . C19 C20 C21 124.9(6) yes . . . C20 C21 C22 124.0(8) yes . . . C20 C21 C26 115.8(6) yes . . . C22 C21 C26 120.2(8) yes . . . C21 C22 C23 119.5(8) yes . . . C22 C23 C24 119.9(7) yes . . . C23 C24 C25 118.1(8) yes . . . N4 C25 C24 118.8(7) yes . . . N4 C25 C26 118.7(6) yes . . . C24 C25 C26 122.5(8) yes . . . C21 C26 C25 119.8(7) yes . . . C1 N1 H1 119.751 no . . . C5 N1 H1 119.750 no . . . C14 N3 H3 118.644 no . . . C18 N3 H3 118.635 no . . . N1 C1 H1A 121.231 no . . . C2 C1 H1A 121.221 no . . . C1 C2 H2 118.376 no . . . C3 C2 H2 118.371 no . . . C3 C4 H4 120.813 no . . . C5 C4 H4 120.818 no . . . N1 C5 H5 119.019 no . . . C4 C5 H5 119.024 no . . . C3 C6 H6 117.627 no . . . C7 C6 H6 117.635 no . . . C6 C7 H7 116.303 no . . . C8 C7 H7 116.295 no . . . C8 C9 H9 118.998 no . . . C10 C9 H9 118.996 no . . . C9 C10 H10 119.224 no . . . C11 C10 H10 119.231 no . . . C10 C11 H11 121.999 no . . . C12 C11 H11 121.999 no . . . C8 C13 H13 120.774 no . . . C12 C13 H13 120.774 no . . . N3 C14 H14 119.034 no . . . C15 C14 H14 119.040 no . . . C14 C15 H15 121.105 no . . . C16 C15 H15 121.106 no . . . C16 C17 H17 119.321 no . . . C18 C17 H17 119.322 no . . . N3 C18 H18 120.372 no . . . C17 C18 H18 120.365 no . . . C16 C19 H19 118.820 no . . . C20 C19 H19 118.821 no . . . C19 C20 H20 117.542 no . . . C21 C20 H20 117.554 no . . . C21 C22 H22 120.263 no . . . C23 C22 H22 120.259 no . . . C22 C23 H23 120.035 no . . . C24 C23 H23 120.034 no . . . C23 C24 H24 120.949 no . . . C25 C24 H24 120.956 no . . . C21 C26 H26 120.115 no . . . C25 C26 H26 120.109 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 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 C1 N1 C5 C4 1.3(11) no . . . . C5 N1 C1 C2 -1.2(11) no . . . . O1 N2 C12 C11 164.8(6) no . . . . O1 N2 C12 C13 -15.0(10) no . . . . O2 N2 C12 C11 -15.1(10) no . . . . O2 N2 C12 C13 165.1(7) no . . . . C14 N3 C18 C17 -0.4(12) no . . . . C18 N3 C14 C15 0.3(12) no . . . . O3 N4 C25 C24 13.2(11) no . . . . O3 N4 C25 C26 -166.2(7) no . . . . O4 N4 C25 C24 -165.3(7) no . . . . O4 N4 C25 C26 15.3(11) no . . . . N1 C1 C2 C3 0.2(12) no . . . . C1 C2 C3 C4 0.7(12) no . . . . C1 C2 C3 C6 -178.8(7) no . . . . C2 C3 C4 C5 -0.6(11) no . . . . C2 C3 C6 C7 -170.8(8) no . . . . C4 C3 C6 C7 9.7(12) no . . . . C6 C3 C4 C5 178.8(6) no . . . . C3 C4 C5 N1 -0.4(11) no . . . . C3 C6 C7 C8 -178.5(7) no . . . . C6 C7 C8 C9 -4.3(13) no . . . . C6 C7 C8 C13 178.3(8) no . . . . C7 C8 C9 C10 -179.2(7) no . . . . C7 C8 C13 C12 178.7(6) no . . . . C9 C8 C13 C12 1.2(11) no . . . . C13 C8 C9 C10 -1.9(12) no . . . . C8 C9 C10 C11 2.5(13) no . . . . C9 C10 C11 C12 -2.4(12) no . . . . C10 C11 C12 N2 -177.9(7) no . . . . C10 C11 C12 C13 1.8(12) no . . . . N2 C12 C13 C8 178.4(6) no . . . . C11 C12 C13 C8 -1.3(12) no . . . . N3 C14 C15 C16 0.2(11) no . . . . C14 C15 C16 C17 -0.6(10) no . . . . C14 C15 C16 C19 178.5(6) no . . . . C15 C16 C17 C18 0.5(10) no . . . . C15 C16 C19 C20 171.4(6) no . . . . C17 C16 C19 C20 -9.7(11) no . . . . C19 C16 C17 C18 -178.5(6) no . . . . C16 C17 C18 N3 -0.1(12) no . . . . C16 C19 C20 C21 -179.0(6) no . . . . C19 C20 C21 C22 0.1(13) no . . . . C19 C20 C21 C26 -178.5(7) no . . . . C20 C21 C22 C23 -179.7(7) no . . . . C20 C21 C26 C25 178.8(6) no . . . . C22 C21 C26 C25 0.2(12) no . . . . C26 C21 C22 C23 -1.2(12) no . . . . C21 C22 C23 C24 1.3(12) no . . . . C22 C23 C24 C25 -0.3(11) no . . . . C23 C24 C25 N4 179.9(7) no . . . . C23 C24 C25 C26 -0.7(12) no . . . . N4 C25 C26 C21 -179.8(6) no . . . . C24 C25 C26 C21 0.8(11) no . . . . loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_publ_flag _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 O1 C11 3.544(9) no . . O1 C13 2.718(10) no . . O2 C11 2.732(11) no . . O2 C13 3.530(11) no . . O3 C24 2.744(11) no . . O3 C26 3.553(11) no . . O4 C24 3.528(8) no . . O4 C26 2.717(11) no . . N1 C3 2.751(10) no . . N3 C16 2.731(10) no . . C1 C4 2.762(12) no . . C2 C5 2.700(10) no . . C4 C7 2.965(11) no . . C6 C9 3.078(12) no . . C8 C11 2.846(12) no . . C9 C12 2.732(12) no . . C10 C13 2.797(10) no . . C14 C17 2.714(12) no . . C15 C18 2.744(9) no . . C17 C20 2.995(11) no . . C19 C22 3.024(11) no . . C21 C24 2.794(12) no . . C22 C25 2.733(12) no . . C23 C26 2.766(9) no . . Cl1 N3 3.048(7) no . 1_454 Cl1 C1 3.570(9) no . 1_545 Cl1 C1 3.509(10) no . 1_645 Cl1 C2 3.551(9) no . 1_545 Cl1 C5 3.495(8) no . 1_655 Cl1 C18 3.555(9) no . 1_454 Cl2 N1 3.004(6) no . 1_656 Cl2 C5 3.549(8) no . 1_656 Cl2 C14 3.510(9) no . 1_465 Cl2 C15 3.521(8) no . 1_565 Cl2 C17 3.587(7) no . 1_455 Cl2 C18 3.479(9) no . 1_455 O1 O2 3.373(9) no . 1_455 O1 C1 3.557(9) no . 1_645 O1 C2 3.242(10) no . 1_645 O1 C6 3.423(9) no . 1_545 O1 C9 3.508(11) no . 1_545 O2 O1 3.373(9) no . 1_655 O2 C13 3.447(10) no . 1_655 O2 C23 3.479(11) no . 1_655 O2 C24 3.573(10) no . 1_655 O2 C24 3.280(10) no . 1_755 O3 O4 3.370(10) no . 1_455 O3 C10 3.438(12) no . 1_455 O3 C11 3.279(10) no . 1_355 O3 C11 3.563(11) no . 1_455 O3 C26 3.495(10) no . 1_455 O4 O3 3.370(10) no . 1_655 O4 C14 3.569(10) no . 1_465 O4 C15 3.220(10) no . 1_465 O4 C19 3.418(8) no . 1_565 O4 C22 3.547(11) no . 1_565 N1 Cl2 3.004(6) no . 1_454 N1 C3 3.434(10) no . 1_455 N1 C6 3.497(10) no . 1_455 N2 C23 3.566(11) no . 1_655 N2 C24 3.433(10) no . 1_655 N3 Cl1 3.048(7) no . 1_656 N3 C16 3.465(10) no . 1_655 N3 C19 3.523(10) no . 1_655 N4 C10 3.587(12) no . 1_455 N4 C11 3.450(11) no . 1_455 C1 Cl1 3.509(10) no . 1_465 C1 Cl1 3.570(9) no . 1_565 C1 O1 3.557(9) no . 1_465 C2 Cl1 3.551(9) no . 1_565 C2 O1 3.242(10) no . 1_465 C3 N1 3.434(10) no . 1_655 C3 C8 3.564(12) no . 1_455 C4 C7 3.269(11) no . 1_455 C4 C8 3.444(11) no . 1_455 C5 Cl1 3.495(8) no . 1_455 C5 Cl2 3.549(8) no . 1_454 C5 C6 3.516(11) no . 1_455 C5 C7 3.377(11) no . 1_455 C5 C18 3.472(11) no . 1_454 C6 O1 3.423(9) no . 1_565 C6 N1 3.497(10) no . 1_655 C6 C5 3.516(11) no . 1_655 C6 C9 3.422(12) no . 1_455 C6 C10 3.584(12) no . 1_455 C7 C4 3.269(11) no . 1_655 C7 C5 3.377(11) no . 1_655 C7 C11 3.563(11) no . 1_455 C8 C3 3.564(12) no . 1_655 C8 C4 3.444(11) no . 1_655 C8 C11 3.438(12) no . 1_455 C9 O1 3.508(11) no . 1_565 C9 C6 3.422(12) no . 1_655 C10 O3 3.438(12) no . 1_655 C10 N4 3.587(12) no . 1_655 C10 C6 3.584(12) no . 1_655 C11 O3 3.563(11) no . 1_655 C11 O3 3.279(10) no . 1_755 C11 N4 3.450(11) no . 1_655 C11 C7 3.563(11) no . 1_655 C11 C8 3.438(12) no . 1_655 C13 O2 3.447(10) no . 1_455 C14 Cl2 3.510(9) no . 1_645 C14 O4 3.569(10) no . 1_645 C15 Cl2 3.521(8) no . 1_545 C15 O4 3.220(10) no . 1_645 C16 N3 3.465(10) no . 1_455 C16 C21 3.530(12) no . 1_655 C16 C22 3.596(11) no . 1_655 C17 Cl2 3.587(7) no . 1_655 C17 C20 3.282(11) no . 1_655 C17 C21 3.440(11) no . 1_655 C18 Cl1 3.555(9) no . 1_656 C18 Cl2 3.479(9) no . 1_655 C18 C5 3.472(11) no . 1_656 C18 C19 3.527(11) no . 1_655 C18 C20 3.393(12) no . 1_655 C19 O4 3.418(8) no . 1_545 C19 N3 3.523(10) no . 1_455 C19 C18 3.527(11) no . 1_455 C19 C22 3.413(11) no . 1_655 C19 C23 3.560(11) no . 1_655 C20 C17 3.282(11) no . 1_455 C20 C18 3.393(12) no . 1_455 C20 C24 3.544(11) no . 1_655 C21 C16 3.530(12) no . 1_455 C21 C17 3.440(11) no . 1_455 C21 C24 3.478(12) no . 1_655 C22 O4 3.547(11) no . 1_545 C22 C16 3.596(11) no . 1_455 C22 C19 3.413(11) no . 1_455 C23 O2 3.479(11) no . 1_455 C23 N2 3.566(11) no . 1_455 C23 C19 3.560(11) no . 1_455 C24 O2 3.280(10) no . 1_355 C24 O2 3.573(10) no . 1_455 C24 N2 3.433(10) no . 1_455 C24 C20 3.544(11) no . 1_455 C24 C21 3.478(12) no . 1_455 C26 O3 3.495(10) no . 1_655 O1 H13 2.4294 no . . O2 H11 2.4686 no . . O3 H24 2.4630 no . . O4 H26 2.4313 no . . N1 H2 3.2206 no . . N1 H4 3.2160 no . . N2 H11 2.6206 no . . N2 H13 2.6043 no . . N3 H15 3.1709 no . . N3 H17 3.1952 no . . N4 H24 2.6264 no . . N4 H26 2.6041 no . . C1 H5 3.2170 no . . C2 H1 3.1578 no . . C2 H4 3.2253 no . . C2 H6 2.6130 no . . C3 H1A 3.2385 no . . C3 H5 3.2511 no . . C3 H7 2.5964 no . . C4 H1 3.1541 no . . C4 H2 3.2187 no . . C4 H6 3.3373 no . . C4 H7 2.6117 no . . C5 H1A 3.2184 no . . C6 H2 2.5737 no . . C6 H4 2.6985 no . . C6 H9 2.8304 no . . C7 H4 2.7051 no . . C7 H9 2.7494 no . . C7 H13 2.6350 no . . C8 H6 2.6622 no . . C8 H10 3.2806 no . . C9 H6 2.7707 no . . C9 H7 3.3774 no . . C9 H11 3.2713 no . . C9 H13 3.3016 no . . C11 H9 3.2634 no . . C11 H13 3.2993 no . . C12 H10 3.2404 no . . C13 H7 2.5849 no . . C13 H9 3.2885 no . . C13 H11 3.3069 no . . C14 H18 3.1665 no . . C15 H3 3.1074 no . . C15 H17 3.2807 no . . C15 H19 2.6319 no . . C16 H14 3.2766 no . . C16 H18 3.2397 no . . C16 H20 2.5825 no . . C17 H3 3.1200 no . . C17 H15 3.2851 no . . C17 H19 3.3669 no . . C17 H20 2.6495 no . . C18 H14 3.1736 no . . C19 H15 2.6520 no . . C19 H17 2.7384 no . . C19 H22 2.7642 no . . C20 H17 2.7393 no . . C20 H22 2.7229 no . . C20 H26 2.5396 no . . C21 H19 2.6706 no . . C21 H23 3.2835 no . . C22 H19 2.7234 no . . C22 H20 3.3535 no . . C22 H24 3.2934 no . . C22 H26 3.2278 no . . C24 H22 3.2790 no . . C24 H26 3.2710 no . . C25 H23 3.2217 no . . C26 H20 2.5549 no . . C26 H22 3.2259 no . . C26 H24 3.2757 no . . H1 H1A 2.3301 no . . H1 H5 2.2168 no . . H1A H2 2.3059 no . . H2 H6 2.3873 no . . H3 H14 2.1544 no . . H3 H18 2.2768 no . . H4 H5 2.3325 no . . H4 H7 2.0903 no . . H6 H7 2.7538 no . . H6 H9 2.2558 no . . H7 H13 2.3920 no . . H9 H10 2.2689 no . . H10 H11 2.3868 no . . H14 H15 2.3339 no . . H15 H19 2.4511 no . . H17 H18 2.2783 no . . H17 H20 2.1300 no . . H19 H20 2.7842 no . . H19 H22 2.1912 no . . H20 H26 2.3103 no . . H22 H23 2.3907 no . . H23 H24 2.3287 no . . Cl1 H1A 3.1973 no . 1_545 Cl1 H1A 2.6869 no . 1_645 Cl1 H2 3.1358 no . 1_545 Cl1 H3 2.2343 no . 1_454 Cl1 H4 3.4256 no . . Cl1 H4 3.1063 no . 1_655 Cl1 H5 2.8586 no . 1_655 Cl1 H7 2.8571 no . . Cl1 H13 2.9832 no . . Cl1 H18 3.2348 no . 1_454 Cl2 H1 2.1780 no . 1_656 Cl2 H5 3.2417 no . 1_656 Cl2 H14 2.6652 no . 1_465 Cl2 H14 3.2682 no . 1_565 Cl2 H15 3.0985 no . 1_565 Cl2 H17 3.0554 no . 1_455 Cl2 H17 3.4731 no . . Cl2 H18 2.8470 no . 1_455 Cl2 H20 2.8729 no . . Cl2 H26 2.9853 no . . O1 H1A 3.5184 no . 1_645 O1 H2 3.3264 no . 1_545 O1 H2 2.9339 no . 1_645 O1 H6 2.5444 no . 1_545 O1 H9 2.6094 no . 1_545 O1 H23 3.3799 no . 1_655 O1 H24 3.5482 no . 1_655 O2 H2 3.3508 no . 1_645 O2 H9 3.3615 no . 1_545 O2 H13 3.2511 no . 1_655 O2 H23 3.4262 no . 1_755 O2 H24 2.4116 no . 1_755 O3 H10 3.5161 no . 1_355 O3 H10 3.5326 no . 1_455 O3 H11 2.4044 no . 1_355 O3 H15 3.3255 no . 1_465 O3 H22 3.3668 no . 1_565 O3 H26 3.2833 no . 1_455 O4 H10 3.4054 no . 1_455 O4 H11 3.5670 no . 1_455 O4 H14 3.5285 no . 1_465 O4 H15 2.9250 no . 1_465 O4 H15 3.2701 no . 1_565 O4 H19 2.5399 no . 1_565 O4 H22 2.6580 no . 1_565 N1 H14 3.1734 no . 1_464 N2 H2 3.2332 no . 1_645 N2 H9 3.3338 no . 1_545 N2 H13 3.5750 no . 1_655 N2 H23 3.5437 no . 1_655 N2 H24 3.3124 no . 1_655 N2 H24 3.5111 no . 1_755 N3 H1A 3.1769 no . 1_646 N4 H10 3.5255 no . 1_455 N4 H11 3.5368 no . 1_355 N4 H11 3.3371 no . 1_455 N4 H15 3.1881 no . 1_465 N4 H22 3.3416 no . 1_565 N4 H26 3.5873 no . 1_455 C1 H3 3.2956 no . 1_464 C1 H14 3.4514 no . 1_464 C2 H1 3.4758 no . 1_655 C3 H1 3.3652 no . 1_655 C4 H7 3.3305 no . 1_455 C4 H18 2.9735 no . 1_454 C5 H7 3.2683 no . 1_455 C5 H17 3.3005 no . 1_454 C5 H18 2.9823 no . 1_454 C7 H4 3.4377 no . 1_655 C8 H4 3.4036 no . 1_655 C8 H11 3.4065 no . 1_455 C9 H6 3.5081 no . 1_655 C9 H23 3.3359 no . 1_665 C10 H6 3.5318 no . 1_655 C10 H22 3.4093 no . 1_665 C11 H24 3.5235 no . 1_655 C12 H7 3.5612 no . 1_655 C12 H24 3.2828 no . 1_655 C13 H4 3.3946 no . 1_655 C13 H7 3.5996 no . 1_655 C13 H11 3.5776 no . 1_455 C14 H1 3.3572 no . 1_646 C14 H1A 3.4709 no . 1_646 C15 H3 3.4986 no . 1_455 C16 H3 3.4082 no . 1_455 C17 H5 2.9620 no . 1_656 C17 H20 3.3894 no . 1_655 C18 H4 3.3276 no . 1_656 C18 H5 2.9675 no . 1_656 C18 H20 3.3358 no . 1_655 C20 H17 3.4291 no . 1_455 C21 H17 3.3925 no . 1_455 C21 H24 3.4554 no . 1_655 C22 H10 3.2762 no . 1_445 C22 H19 3.5144 no . 1_455 C23 H9 3.4190 no . 1_445 C23 H19 3.5167 no . 1_455 C24 H11 3.5516 no . 1_455 C25 H11 3.3053 no . 1_455 C25 H20 3.5002 no . 1_455 C26 H17 3.3969 no . 1_455 C26 H20 3.5324 no . 1_455 C26 H24 3.5862 no . 1_655 H1 Cl2 2.1780 no . 1_454 H1 C2 3.4758 no . 1_455 H1 C3 3.3652 no . 1_455 H1 C14 3.3572 no . 1_464 H1 H14 2.8728 no . 1_464 H1A Cl1 2.6869 no . 1_465 H1A Cl1 3.1973 no . 1_565 H1A O1 3.5184 no . 1_465 H1A N3 3.1769 no . 1_464 H1A C14 3.4709 no . 1_464 H1A H2 3.5590 no . 1_455 H1A H3 2.8296 no . 1_464 H1A H13 3.5338 no . 1_465 H1A H14 3.3566 no . 1_464 H2 Cl1 3.1358 no . 1_565 H2 O1 2.9339 no . 1_465 H2 O1 3.3264 no . 1_565 H2 O2 3.3508 no . 1_465 H2 N2 3.2332 no . 1_465 H2 H1A 3.5590 no . 1_655 H2 H13 3.0598 no . 1_565 H3 Cl1 2.2343 no . 1_656 H3 C1 3.2956 no . 1_646 H3 C15 3.4986 no . 1_655 H3 C16 3.4082 no . 1_655 H3 H1A 2.8296 no . 1_646 H4 Cl1 3.1063 no . 1_455 H4 Cl1 3.4256 no . . H4 C7 3.4377 no . 1_455 H4 C8 3.4036 no . 1_455 H4 C13 3.3946 no . 1_455 H4 C18 3.3276 no . 1_454 H4 H5 3.5563 no . 1_655 H4 H7 3.3540 no . 1_455 H4 H13 3.3709 no . 1_455 H4 H18 2.7336 no . 1_454 H5 Cl1 2.8586 no . 1_455 H5 Cl2 3.2417 no . 1_454 H5 C17 2.9620 no . 1_454 H5 C18 2.9675 no . 1_454 H5 H4 3.5563 no . 1_455 H5 H7 3.2445 no . 1_455 H5 H17 2.7087 no . 1_454 H5 H18 2.8263 no . 1_354 H5 H18 2.7288 no . 1_454 H6 O1 2.5444 no . 1_565 H6 C9 3.5081 no . 1_455 H6 C10 3.5318 no . 1_455 H6 H9 3.5366 no . 1_455 H7 Cl1 2.8571 no . . H7 C4 3.3305 no . 1_655 H7 C5 3.2683 no . 1_655 H7 C12 3.5612 no . 1_455 H7 C13 3.5996 no . 1_455 H7 H4 3.3540 no . 1_655 H7 H5 3.2445 no . 1_655 H9 O1 2.6094 no . 1_565 H9 O2 3.3615 no . 1_565 H9 N2 3.3338 no . 1_565 H9 C23 3.4190 no . 1_665 H9 H6 3.5366 no . 1_655 H9 H23 2.7222 no . 1_665 H10 O3 3.5326 no . 1_655 H10 O3 3.5161 no . 1_755 H10 O4 3.4054 no . 1_655 H10 N4 3.5255 no . 1_655 H10 C22 3.2762 no . 1_665 H10 H22 2.6607 no . 1_665 H10 H23 3.3033 no . 1_665 H10 H23 2.9097 no . 1_765 H11 O3 2.4044 no . 1_755 H11 O4 3.5670 no . 1_655 H11 N4 3.3371 no . 1_655 H11 N4 3.5368 no . 1_755 H11 C8 3.4065 no . 1_655 H11 C13 3.5776 no . 1_655 H11 C24 3.5516 no . 1_655 H11 C25 3.3053 no . 1_655 H11 H24 2.7501 no . 1_755 H13 Cl1 2.9832 no . . H13 O2 3.2511 no . 1_455 H13 N2 3.5750 no . 1_455 H13 H1A 3.5338 no . 1_645 H13 H2 3.0598 no . 1_545 H13 H4 3.3709 no . 1_655 H14 Cl2 3.2682 no . 1_545 H14 Cl2 2.6652 no . 1_645 H14 O4 3.5285 no . 1_645 H14 N1 3.1734 no . 1_646 H14 C1 3.4514 no . 1_646 H14 H1 2.8728 no . 1_646 H14 H1A 3.3566 no . 1_646 H14 H15 3.5400 no . 1_655 H15 Cl2 3.0985 no . 1_545 H15 O3 3.3255 no . 1_645 H15 O4 3.2701 no . 1_545 H15 O4 2.9250 no . 1_645 H15 N4 3.1881 no . 1_645 H15 H14 3.5400 no . 1_455 H15 H26 3.0411 no . 1_545 H17 Cl2 3.4731 no . . H17 Cl2 3.0554 no . 1_655 H17 C5 3.3005 no . 1_656 H17 C20 3.4291 no . 1_655 H17 C21 3.3925 no . 1_655 H17 C26 3.3969 no . 1_655 H17 H5 2.7087 no . 1_656 H17 H18 3.5748 no . 1_455 H17 H20 3.3849 no . 1_655 H17 H26 3.3539 no . 1_655 H18 Cl1 3.2348 no . 1_656 H18 Cl2 2.8470 no . 1_655 H18 C4 2.9735 no . 1_656 H18 C5 2.9823 no . 1_656 H18 H4 2.7336 no . 1_656 H18 H5 2.7288 no . 1_656 H18 H5 2.8263 no . 1_756 H18 H17 3.5748 no . 1_655 H18 H20 3.2976 no . 1_655 H19 O4 2.5399 no . 1_545 H19 C22 3.5144 no . 1_655 H19 C23 3.5167 no . 1_655 H19 H22 3.5774 no . 1_655 H19 H23 3.5628 no . 1_655 H20 Cl2 2.8729 no . . H20 C17 3.3894 no . 1_455 H20 C18 3.3358 no . 1_455 H20 C25 3.5002 no . 1_655 H20 C26 3.5324 no . 1_655 H20 H17 3.3849 no . 1_455 H20 H18 3.2976 no . 1_455 H22 O3 3.3668 no . 1_545 H22 O4 2.6580 no . 1_545 H22 N4 3.3416 no . 1_545 H22 C10 3.4093 no . 1_445 H22 H10 2.6607 no . 1_445 H22 H19 3.5774 no . 1_455 H22 H23 3.5241 no . 1_655 H23 O1 3.3799 no . 1_455 H23 O2 3.4262 no . 1_355 H23 N2 3.5437 no . 1_455 H23 C9 3.3359 no . 1_445 H23 H9 2.7222 no . 1_445 H23 H10 2.9097 no . 1_345 H23 H10 3.3033 no . 1_445 H23 H19 3.5628 no . 1_455 H23 H22 3.5241 no . 1_455 H24 O1 3.5482 no . 1_455 H24 O2 2.4116 no . 1_355 H24 N2 3.5111 no . 1_355 H24 N2 3.3124 no . 1_455 H24 C11 3.5235 no . 1_455 H24 C12 3.2828 no . 1_455 H24 C21 3.4554 no . 1_455 H24 C26 3.5862 no . 1_455 H24 H11 2.7501 no . 1_355 H26 Cl2 2.9853 no . . H26 O3 3.2833 no . 1_655 H26 N4 3.5873 no . 1_655 H26 H15 3.0411 no . 1_565 H26 H17 3.3539 no . 1_455 #============================================================================== loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_D _geom_hbond_site_symmetry_H _geom_hbond_site_symmetry_A _geom_hbond_distance_DA _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_angle_DHA _geom_hbond_publ_flag N1 H1 Cl2 . . 1_454 3.004(6) 0.880 2.178 156.1 no N3 H3 Cl1 . . 1_656 3.048(7) 0.880 2.234 153.6 no data_STYRYLPYCF3HCL-4 _database_code_depnum_ccdc_archive 'CCDC 901991' #TrackingRef '4.cif' #============================================================================== # CHEMICAL DATA _chemical_formula_sum 'C14 H11 Cl F3 N' _chemical_formula_moiety 'C14 H11 Cl F3 N' _chemical_formula_weight 285.70 _chemical_melting_point ? #============================================================================== # CRYSTAL DATA _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_Int_Tables_number 2 loop_ _symmetry_equiv_pos_site_id _symmetry_equiv_pos_as_xyz 1 +X,+Y,+Z 2 -X,-Y,-Z #------------------------------------------------------------------------------ _cell_length_a 5.0232(3) _cell_length_b 7.3643(3) _cell_length_c 17.3038(8) _cell_angle_alpha 92.657(3) _cell_angle_beta 91.992(3) _cell_angle_gamma 92.424(4) _cell_volume 638.42(5) _cell_formula_units_Z 2 _cell_measurement_reflns_used 2107 _cell_measurement_theta_min 5.12 _cell_measurement_theta_max 68.22 _cell_measurement_temperature 123 #------------------------------------------------------------------------------ _exptl_crystal_description platelet _exptl_crystal_colour colorless _exptl_crystal_size_max 0.250 _exptl_crystal_size_mid 0.100 _exptl_crystal_size_min 0.050 _exptl_crystal_density_diffrn 1.486 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 292.00 _exptl_absorpt_coefficient_mu 2.874 _exptl_absorpt_correction_type none #============================================================================== # EXPERIMENTAL DATA _diffrn_ambient_temperature 123 _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54187 _diffrn_measurement_device_type 'Rigaku R-AXIS RAPID' _diffrn_measurement_method \w _diffrn_detector_area_resol_mean 10.000 _diffrn_reflns_number 6734 _diffrn_reflns_av_R_equivalents 0.0899 _diffrn_reflns_theta_max 68.24 _diffrn_reflns_theta_full 68.25 _diffrn_measured_fraction_theta_max 0.976 _diffrn_measured_fraction_theta_full 0.976 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_decay_% ? #============================================================================== # REFINEMENT DATA _refine_special_details ; Refinement was performed using all reflections. The weighted R-factor (wR) and goodness of fit (S) are based on F^2^. R-factor (gt) are based on F. The threshold expression of F^2^ > 2.0 sigma(F^2^) is used only for calculating R-factor (gt). ; _reflns_number_total 2267 _reflns_number_gt 1655 _reflns_threshold_expression F^2^>2.0\s(F^2^) _refine_ls_structure_factor_coef Fsqd _refine_ls_R_factor_gt 0.0631 _refine_ls_wR_factor_ref 0.1487 _refine_ls_number_restraints 0 _refine_ls_hydrogen_treatment constr _refine_ls_number_reflns 2267 _refine_ls_number_parameters 172 _refine_ls_goodness_of_fit_ref 0.992 _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'w = 1/[\s^2^(Fo^2^)+(0.0701P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _refine_ls_shift/su_max 0.000 _refine_diff_density_max 0.450 _refine_diff_density_min -0.350 _refine_ls_extinction_method none _refine_ls_extinction_coef ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.018 0.009 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; H H 0.000 0.000 ; International Tables for Crystallography (1992, Vol. C, Table 6.1.1.4) ; N N 0.031 0.018 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; F F 0.073 0.053 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; Cl Cl 0.364 0.702 ; International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4) ; #============================================================================== # ATOMIC COORDINATES AND THERMAL PARAMETERS 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 0.41384(15) 0.78431(9) 0.93924(4) 0.0322(3) Uani 1.0 2 d . . . F1 F -0.2201(5) 0.8977(4) 0.52371(13) 0.0799(9) Uani 1.0 2 d . . . F2 F -0.4337(5) 0.9574(3) 0.62525(13) 0.0669(7) Uani 1.0 2 d . . . F3 F -0.5584(5) 0.7320(3) 0.54988(11) 0.0575(7) Uani 1.0 2 d . . . N1 N 1.1228(6) 0.1488(4) 0.92328(13) 0.0317(7) Uani 1.0 2 d . . . C1 C 0.9401(7) 0.0531(4) 0.87871(18) 0.0353(8) Uani 1.0 2 d . . . C2 C 0.7508(7) 0.1403(4) 0.83696(17) 0.0334(8) Uani 1.0 2 d . . . C3 C 0.7487(6) 0.3293(4) 0.84149(16) 0.0278(7) Uani 1.0 2 d . . . C4 C 0.9396(7) 0.4226(4) 0.89071(16) 0.0297(7) Uani 1.0 2 d . . . C5 C 1.1260(7) 0.3311(4) 0.93057(16) 0.0303(8) Uani 1.0 2 d . . . C6 C 0.5554(7) 0.4346(4) 0.79999(16) 0.0312(8) Uani 1.0 2 d . . . C7 C 0.3911(7) 0.3775(4) 0.74103(17) 0.0330(8) Uani 1.0 2 d . . . C8 C 0.1979(7) 0.4898(4) 0.70271(17) 0.0328(8) Uani 1.0 2 d . . . C9 C 0.1552(7) 0.6680(5) 0.72952(18) 0.0371(8) Uani 1.0 2 d . . . C10 C -0.0229(7) 0.7729(5) 0.69122(17) 0.0367(8) Uani 1.0 2 d . . . C11 C -0.1629(7) 0.7034(5) 0.62557(17) 0.0344(8) Uani 1.0 2 d . . . C12 C -0.1293(7) 0.5258(5) 0.59922(18) 0.0388(9) Uani 1.0 2 d . . . C13 C 0.0501(7) 0.4202(5) 0.63727(18) 0.0383(8) Uani 1.0 2 d . . . C14 C -0.3436(8) 0.8221(5) 0.58149(19) 0.0417(9) Uani 1.0 2 d . . . H1 H 1.2450 0.0906 0.9487 0.0380 Uiso 1.0 2 calc R . . H1A H 0.9409 -0.0760 0.8759 0.0423 Uiso 1.0 2 calc R . . H2 H 0.6216 0.0717 0.8051 0.0400 Uiso 1.0 2 calc R . . H4 H 0.9395 0.5515 0.8965 0.0356 Uiso 1.0 2 calc R . . H5 H 1.2570 0.3958 0.9632 0.0364 Uiso 1.0 2 calc R . . H6 H 0.5457 0.5586 0.8170 0.0374 Uiso 1.0 2 calc R . . H7 H 0.4000 0.2546 0.7224 0.0396 Uiso 1.0 2 calc R . . H9 H 0.2501 0.7174 0.7747 0.0445 Uiso 1.0 2 calc R . . H10 H -0.0494 0.8938 0.7101 0.0440 Uiso 1.0 2 calc R . . H12 H -0.2293 0.4763 0.5550 0.0465 Uiso 1.0 2 calc R . . H13 H 0.0730 0.2986 0.6186 0.0459 Uiso 1.0 2 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_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 Cl1 0.0348(5) 0.0209(4) 0.0402(5) 0.0004(3) -0.0033(4) -0.0015(3) F1 0.0512(16) 0.106(2) 0.0894(18) 0.0101(15) 0.0107(14) 0.0642(15) F2 0.0756(19) 0.0549(14) 0.0696(15) 0.0284(13) -0.0251(13) -0.0070(11) F3 0.0468(15) 0.0575(14) 0.0663(14) -0.0012(11) -0.0216(11) 0.0046(11) N1 0.0304(17) 0.0290(14) 0.0364(14) 0.0046(12) 0.0034(12) 0.0052(11) C1 0.035(2) 0.0239(17) 0.0469(19) -0.0007(15) 0.0037(16) 0.0006(14) C2 0.028(2) 0.0285(17) 0.0431(18) -0.0016(14) -0.0016(15) -0.0032(13) C3 0.0235(18) 0.0283(16) 0.0323(16) 0.0035(13) 0.0063(13) 0.0016(12) C4 0.0298(19) 0.0224(15) 0.0368(17) -0.0008(13) 0.0032(14) 0.0014(12) C5 0.0265(19) 0.0285(16) 0.0355(17) -0.0010(14) 0.0024(14) -0.0013(13) C6 0.0296(19) 0.0267(16) 0.0369(17) 0.0004(14) 0.0028(14) -0.0010(13) C7 0.033(2) 0.0268(16) 0.0393(18) 0.0020(14) 0.0061(15) -0.0039(13) C8 0.031(2) 0.0333(18) 0.0347(17) 0.0031(14) 0.0034(14) 0.0012(13) C9 0.036(3) 0.0370(18) 0.0374(18) 0.0021(16) -0.0043(15) -0.0028(14) C10 0.037(3) 0.0350(18) 0.0381(18) 0.0048(16) -0.0001(15) 0.0005(14) C11 0.0276(19) 0.0391(19) 0.0368(18) 0.0009(15) 0.0009(14) 0.0065(14) C12 0.037(3) 0.041(2) 0.0364(18) -0.0012(16) -0.0060(16) -0.0011(14) C13 0.039(3) 0.0343(18) 0.0406(18) 0.0003(16) 0.0031(16) -0.0029(14) C14 0.035(3) 0.046(3) 0.0426(19) -0.0037(17) -0.0039(16) 0.0057(16) #============================================================================== _computing_data_collection 'RAPID AUTO (Rigaku, ????)' _computing_cell_refinement 'RAPID AUTO' _computing_data_reduction 'RAPID AUTO' _computing_structure_solution 'SIR92 (Altomare, et al., 1994)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 2008)' _computing_publication_material 'CrystalStructure 4.0 (Rigaku, 2010)' _computing_molecular_graphics 'CrystalStructure 4.0' #============================================================================== # MOLECULAR GEOMETRY _geom_special_details ; ENTER SPECIAL DETAILS OF THE MOLECULAR GEOMETRY ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 F1 C14 1.327(5) yes . . F2 C14 1.328(5) yes . . F3 C14 1.329(4) yes . . N1 C1 1.334(4) yes . . N1 C5 1.342(4) yes . . C1 C2 1.373(5) yes . . C2 C3 1.391(4) yes . . C3 C4 1.396(4) yes . . C3 C6 1.458(5) yes . . C4 C5 1.363(5) yes . . C6 C7 1.331(4) yes . . C7 C8 1.463(5) yes . . C8 C9 1.399(5) yes . . C8 C13 1.397(5) yes . . C9 C10 1.379(5) yes . . C10 C11 1.381(5) yes . . C11 C12 1.385(5) yes . . C11 C14 1.500(5) yes . . C12 C13 1.384(5) yes . . N1 H1 0.880 no . . C1 H1A 0.950 no . . C2 H2 0.950 no . . C4 H4 0.950 no . . C5 H5 0.950 no . . C6 H6 0.950 no . . C7 H7 0.950 no . . C9 H9 0.950 no . . C10 H10 0.950 no . . C12 H12 0.950 no . . C13 H13 0.950 no . . 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 _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_2 _geom_angle_site_symmetry_3 C1 N1 C5 122.0(3) yes . . . N1 C1 C2 120.3(3) yes . . . C1 C2 C3 119.8(3) yes . . . C2 C3 C4 117.5(3) yes . . . C2 C3 C6 124.1(3) yes . . . C4 C3 C6 118.4(3) yes . . . C3 C4 C5 120.8(3) yes . . . N1 C5 C4 119.4(3) yes . . . C3 C6 C7 127.6(3) yes . . . C6 C7 C8 124.9(3) yes . . . C7 C8 C9 121.9(3) yes . . . C7 C8 C13 120.1(3) yes . . . C9 C8 C13 118.1(3) yes . . . C8 C9 C10 120.8(3) yes . . . C9 C10 C11 120.4(3) yes . . . C10 C11 C12 119.8(3) yes . . . C10 C11 C14 120.1(3) yes . . . C12 C11 C14 120.2(3) yes . . . C11 C12 C13 120.0(3) yes . . . C8 C13 C12 120.9(3) yes . . . F1 C14 F2 106.6(3) yes . . . F1 C14 F3 106.2(3) yes . . . F1 C14 C11 111.5(3) yes . . . F2 C14 F3 106.0(3) yes . . . F2 C14 C11 112.9(3) yes . . . F3 C14 C11 113.1(3) yes . . . C1 N1 H1 118.999 no . . . C5 N1 H1 118.994 no . . . N1 C1 H1A 119.842 no . . . C2 C1 H1A 119.849 no . . . C1 C2 H2 120.084 no . . . C3 C2 H2 120.076 no . . . C3 C4 H4 119.579 no . . . C5 C4 H4 119.578 no . . . N1 C5 H5 120.276 no . . . C4 C5 H5 120.281 no . . . C3 C6 H6 116.196 no . . . C7 C6 H6 116.183 no . . . C6 C7 H7 117.556 no . . . C8 C7 H7 117.545 no . . . C8 C9 H9 119.598 no . . . C10 C9 H9 119.601 no . . . C9 C10 H10 119.792 no . . . C11 C10 H10 119.797 no . . . C11 C12 H12 119.982 no . . . C13 C12 H12 119.985 no . . . C8 C13 H13 119.555 no . . . C12 C13 H13 119.550 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 _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 C1 N1 C5 C4 -0.8(5) no . . . . C5 N1 C1 C2 1.5(5) no . . . . N1 C1 C2 C3 -0.3(5) no . . . . C1 C2 C3 C4 -1.5(5) no . . . . C1 C2 C3 C6 -179.6(3) no . . . . C2 C3 C4 C5 2.2(5) no . . . . C2 C3 C6 C7 -15.0(5) no . . . . C4 C3 C6 C7 166.9(3) no . . . . C6 C3 C4 C5 -179.6(3) no . . . . C3 C4 C5 N1 -1.1(5) no . . . . C3 C6 C7 C8 178.8(3) no . . . . C6 C7 C8 C9 -5.0(5) no . . . . C6 C7 C8 C13 174.8(3) no . . . . C7 C8 C9 C10 178.3(3) no . . . . C7 C8 C13 C12 -178.5(3) no . . . . C9 C8 C13 C12 1.3(5) no . . . . C13 C8 C9 C10 -1.6(5) no . . . . C8 C9 C10 C11 0.1(5) no . . . . C9 C10 C11 C12 1.7(5) no . . . . C9 C10 C11 C14 -176.2(3) no . . . . C10 C11 C12 C13 -1.9(5) no . . . . C10 C11 C14 F1 94.4(4) no . . . . C10 C11 C14 F2 -25.6(5) no . . . . C10 C11 C14 F3 -146.0(3) no . . . . C12 C11 C14 F1 -83.5(4) no . . . . C12 C11 C14 F2 156.5(3) no . . . . C12 C11 C14 F3 36.1(5) no . . . . C14 C11 C12 C13 176.0(3) no . . . . C11 C12 C13 C8 0.4(5) no . . . . loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_publ_flag _geom_contact_site_symmetry_1 _geom_contact_site_symmetry_2 F1 C10 3.217(4) no . . F1 C12 3.133(5) no . . F2 C10 2.762(4) no . . F3 C10 3.566(4) no . . F3 C12 2.820(4) no . . N1 C3 2.739(4) no . . C1 C4 2.720(5) no . . C2 C5 2.739(4) no . . C2 C7 3.066(5) no . . C6 C9 2.966(5) no . . C8 C11 2.794(5) no . . C9 C12 2.766(5) no . . C10 C13 2.763(5) no . . Cl1 N1 3.129(3) no . 1_465 Cl1 N1 3.275(3) no . 2_767 Cl1 C1 3.331(4) no . 1_465 Cl1 C1 3.456(4) no . 1_565 Cl1 C4 3.549(3) no . 1_455 Cl1 C5 3.575(3) no . 1_455 Cl1 C5 3.335(3) no . 2_767 Cl1 C6 3.555(3) no . . F1 F1 3.341(4) no . 2_476 F1 F1 2.792(4) no . 2_576 F1 F2 3.302(4) no . 2_476 F1 F3 3.283(4) no . 2_476 F1 C14 3.582(5) no . 2_476 F2 F1 3.302(4) no . 2_476 F2 C9 3.508(4) no . 1_455 F2 C10 3.456(4) no . 1_455 F3 F1 3.283(4) no . 2_476 F3 C8 3.486(4) no . 1_455 F3 C9 3.513(4) no . 1_455 F3 C10 3.450(4) no . 1_455 F3 C11 3.351(4) no . 1_455 F3 C12 3.344(4) no . 1_455 F3 C12 3.426(4) no . 2_466 F3 C13 3.403(4) no . 1_455 N1 Cl1 3.129(3) no . 1_645 N1 Cl1 3.275(3) no . 2_767 N1 C2 3.538(5) no . 1_655 C1 Cl1 3.456(4) no . 1_545 C1 Cl1 3.331(4) no . 1_645 C2 N1 3.538(5) no . 1_455 C3 C5 3.535(5) no . 1_455 C3 C8 3.559(5) no . 1_655 C4 Cl1 3.549(3) no . 1_655 C4 C5 3.544(4) no . 2_767 C4 C6 3.517(5) no . 1_655 C4 C7 3.515(5) no . 1_655 C4 C8 3.592(5) no . 1_655 C4 C9 3.568(5) no . 1_655 C5 Cl1 3.575(3) no . 1_655 C5 Cl1 3.335(3) no . 2_767 C5 C3 3.535(5) no . 1_655 C5 C4 3.544(4) no . 2_767 C5 C6 3.271(5) no . 1_655 C6 Cl1 3.555(3) no . . C6 C4 3.517(5) no . 1_455 C6 C5 3.271(5) no . 1_455 C7 C4 3.515(5) no . 1_455 C8 F3 3.486(4) no . 1_655 C8 C3 3.559(5) no . 1_455 C8 C4 3.592(5) no . 1_455 C9 F2 3.508(4) no . 1_655 C9 F3 3.513(4) no . 1_655 C9 C4 3.568(5) no . 1_455 C10 F2 3.456(4) no . 1_655 C10 F3 3.450(4) no . 1_655 C11 F3 3.351(4) no . 1_655 C12 F3 3.344(4) no . 1_655 C12 F3 3.426(4) no . 2_466 C13 F3 3.403(4) no . 1_655 C14 F1 3.582(5) no . 2_476 F1 H10 3.3103 no . . F1 H12 3.1732 no . . F2 H10 2.4588 no . . F3 H12 2.5601 no . . N1 H2 3.2032 no . . N1 H4 3.1918 no . . C1 H5 3.1937 no . . C2 H1 3.1374 no . . C2 H4 3.2450 no . . C2 H6 3.3183 no . . C2 H7 2.7890 no . . C3 H1A 3.2502 no . . C3 H5 3.2592 no . . C3 H7 2.6792 no . . C4 H1 3.1267 no . . C4 H2 3.2490 no . . C4 H6 2.5794 no . . C5 H1A 3.1921 no . . C6 H2 2.7121 no . . C6 H4 2.5987 no . . C6 H9 2.6808 no . . C7 H2 2.8286 no . . C7 H9 2.6735 no . . C7 H13 2.6359 no . . C8 H6 2.6105 no . . C8 H10 3.2705 no . . C8 H12 3.2747 no . . C9 H6 2.6135 no . . C9 H7 3.3302 no . . C9 H13 3.2585 no . . C10 H12 3.2500 no . . C11 H9 3.2490 no . . C11 H13 3.2527 no . . C12 H10 3.2495 no . . C13 H7 2.6297 no . . C13 H9 3.2585 no . . C14 H10 2.6481 no . . C14 H12 2.6564 no . . H1 H1A 2.2342 no . . H1 H5 2.2481 no . . H1A H2 2.3223 no . . H2 H7 2.3002 no . . H4 H5 2.3113 no . . H4 H6 2.3733 no . . H6 H7 2.7688 no . . H6 H9 2.0638 no . . H7 H13 2.4337 no . . H9 H10 2.3200 no . . H12 H13 2.3272 no . . Cl1 H1 2.4436 no . 1_465 Cl1 H1 2.6487 no . 2_767 Cl1 H1A 2.8344 no . 1_465 Cl1 H1A 3.0574 no . 1_565 Cl1 H2 3.3762 no . 1_565 Cl1 H4 2.9289 no . 1_455 Cl1 H4 3.2953 no . . Cl1 H5 2.9867 no . 1_455 Cl1 H5 2.7460 no . 2_767 Cl1 H6 2.7456 no . . Cl1 H9 2.9500 no . . F1 H13 3.5494 no . 1_565 F1 H13 2.9311 no . 2_566 F2 H2 3.1848 no . 1_465 F2 H7 2.8679 no . 1_465 F2 H9 3.5783 no . 1_455 F2 H10 3.4926 no . 1_455 F2 H13 3.5087 no . 1_565 F3 H12 2.5010 no . 2_466 N1 H1 3.4356 no . 2_757 N1 H1A 3.5647 no . 2_757 N1 H2 3.3396 no . 1_655 C1 H1 3.3629 no . 2_757 C1 H9 3.4478 no . 1_645 C1 H10 3.0967 no . 1_645 C2 H1 3.2640 no . 1_455 C2 H10 3.0099 no . 1_645 C3 H5 3.3387 no . 1_455 C4 H5 3.0201 no . 2_767 C4 H6 3.4683 no . 1_655 C4 H9 3.3931 no . 1_655 C5 H4 3.1086 no . 2_767 C5 H5 3.3693 no . 2_767 C5 H6 3.3773 no . 1_655 C6 H5 3.2622 no . 1_455 C9 H1A 3.3228 no . 1_465 C9 H4 3.2599 no . 1_455 C9 H6 3.5417 no . 1_455 C10 H1A 3.3474 no . 1_465 C10 H2 3.4766 no . 1_465 C10 H6 3.5049 no . 1_455 C12 H12 3.2707 no . 2_566 C13 H12 3.5841 no . 2_566 H1 Cl1 2.4436 no . 1_645 H1 Cl1 2.6487 no . 2_767 H1 N1 3.4356 no . 2_757 H1 C1 3.3629 no . 2_757 H1 C2 3.2640 no . 1_655 H1 H1 3.3529 no . 2_757 H1 H1 3.4190 no . 2_857 H1 H1A 3.2129 no . 2_757 H1 H2 3.1767 no . 1_655 H1A Cl1 3.0574 no . 1_545 H1A Cl1 2.8344 no . 1_645 H1A N1 3.5647 no . 2_757 H1A C9 3.3228 no . 1_645 H1A C10 3.3474 no . 1_645 H1A H1 3.2129 no . 2_757 H1A H4 2.7821 no . 1_545 H1A H6 3.3723 no . 1_545 H1A H9 2.8169 no . 1_645 H1A H10 2.8685 no . 1_645 H2 Cl1 3.3762 no . 1_545 H2 F2 3.1848 no . 1_645 H2 N1 3.3396 no . 1_455 H2 C10 3.4766 no . 1_645 H2 H1 3.1767 no . 1_455 H2 H9 3.1564 no . 1_545 H2 H10 2.7055 no . 1_645 H4 Cl1 3.2953 no . . H4 Cl1 2.9289 no . 1_655 H4 C5 3.1086 no . 2_767 H4 C9 3.2599 no . 1_655 H4 H1A 2.7821 no . 1_565 H4 H5 2.6697 no . 2_767 H4 H6 3.3838 no . 1_655 H4 H9 2.9456 no . 1_655 H5 Cl1 2.9867 no . 1_655 H5 Cl1 2.7460 no . 2_767 H5 C3 3.3387 no . 1_655 H5 C4 3.0201 no . 2_767 H5 C5 3.3693 no . 2_767 H5 C6 3.2622 no . 1_655 H5 H4 2.6697 no . 2_767 H5 H5 3.3198 no . 2_767 H5 H5 3.0364 no . 2_867 H5 H6 3.2140 no . 1_655 H6 Cl1 2.7456 no . . H6 C4 3.4683 no . 1_455 H6 C5 3.3773 no . 1_455 H6 C9 3.5417 no . 1_655 H6 C10 3.5049 no . 1_655 H6 H1A 3.3723 no . 1_565 H6 H4 3.3838 no . 1_455 H6 H5 3.2140 no . 1_455 H7 F2 2.8679 no . 1_645 H7 H10 3.4071 no . 1_545 H9 Cl1 2.9500 no . . H9 F2 3.5783 no . 1_655 H9 C1 3.4478 no . 1_465 H9 C4 3.3931 no . 1_455 H9 H1A 2.8169 no . 1_465 H9 H2 3.1564 no . 1_565 H9 H4 2.9456 no . 1_455 H10 F2 3.4926 no . 1_655 H10 C1 3.0967 no . 1_465 H10 C2 3.0099 no . 1_465 H10 H1A 2.8685 no . 1_465 H10 H2 2.7055 no . 1_465 H10 H7 3.4071 no . 1_565 H10 H13 3.4820 no . 1_565 H12 F3 2.5010 no . 2_466 H12 C12 3.2707 no . 2_566 H12 C13 3.5841 no . 2_566 H12 H12 3.3051 no . 2_466 H12 H12 3.0575 no . 2_566 H12 H13 3.5925 no . 2_566 H13 F1 3.5494 no . 1_545 H13 F1 2.9311 no . 2_566 H13 F2 3.5087 no . 1_545 H13 H10 3.4820 no . 1_545 H13 H12 3.5925 no . 2_566 #============================================================================== loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_D _geom_hbond_site_symmetry_H _geom_hbond_site_symmetry_A _geom_hbond_distance_DA _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_angle_DHA _geom_hbond_publ_flag N1 H1 Cl1 . . 1_645 3.129(3) 0.880 2.444 135.1 no N1 H1 Cl1 . . 2_767 3.275(3) 0.880 2.649 129.1 no #============================================================================== # Additional structures and associated data_? identifiers # should be added at this point if there is more than one # structure analysis in the CIF. #============================================================================== # End of CIF #==============================================================================