# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # 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_compound_1b _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C17 H21 Cl N2 O4' _chemical_formula_sum 'C17 H21 Cl N2 O4' _chemical_formula_weight 352.81 _chemical_absolute_configuration ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_H-M_alt 'P 21/c' _space_group_name_Hall '-P 2ybc' _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 11.6880(10) _cell_length_b 17.404(3) _cell_length_c 9.965(2) _cell_angle_alpha 90 _cell_angle_beta 113.76(5) _cell_angle_gamma 90 _cell_volume 1855.2(8) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3513 _cell_measurement_theta_min 0.407 _cell_measurement_theta_max 25.350 _exptl_crystal_description 'thick plate' _exptl_crystal_colour 'pale yellow' _exptl_crystal_size_max 0.53 _exptl_crystal_size_mid 0.36 _exptl_crystal_size_min 0.14 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.263 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 744 _exptl_absorpt_coefficient_mu 0.228 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.88 _exptl_absorpt_correction_T_max 0.96 _exptl_absorpt_process_details 'Scalepack (Otwinowski & Minor, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_source 'fine-focus sealed tube' _diffrn_source_type 'Nonius Kappa CCD' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius kappa-CCD diffractometer' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 9 _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 22970 _diffrn_reflns_av_unetI/netI 0.0387 _diffrn_reflns_av_R_equivalents 0.0219 _diffrn_reflns_limit_h_min -14 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_k_min -20 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_theta_min 3.266 _diffrn_reflns_theta_max 25.362 _diffrn_reflns_theta_full 25.241 _diffrn_measured_fraction_theta_max 0.995 _diffrn_measured_fraction_theta_full 0.995 _diffrn_reflns_Laue_measured_fraction_max 0.995 _diffrn_reflns_Laue_measured_fraction_full 0.995 _diffrn_reflns_point_group_measured_fraction_max 0.995 _diffrn_reflns_point_group_measured_fraction_full 0.995 _reflns_number_total 3381 _reflns_number_gt 2301 _reflns_threshold_expression 'I > 2\s(I)' _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_max . _reflns_Friedel_fraction_full . _reflns_special_details ; Reflections were merged by SHELXL according to the crystal class for the calculation of statistics and refinement. _reflns_Friedel_fraction is defined as the number of unique Friedel pairs measured divided by the number that would be possible theoretically, ignoring centric projections and systematic absences. ; _computing_data_collection 'DENZO (Otwinowski & Minor, 1997); COLLECT (Nonius B.V., 1999)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997); COLLECT (Nonius B.V., 1999)' _computing_data_reduction 'SCALEPACK (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-2012 (Sheldrick, 2012);CRYSTALBUILDER (Welter, 2006)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material 'SHELXL97 (Sheldrick, 2008)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. Seven reflections were OMITted due to beamstop shading. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; w=1/[\s^2^(Fo^2^)+(0.0723P)^2^+0.3807P] where P=(Fo^2^+2Fc^2^)/3 ; _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment mixed _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.036(5) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3381 _refine_ls_number_parameters 231 _refine_ls_number_restraints 21 _refine_ls_R_factor_all 0.0762 _refine_ls_R_factor_gt 0.0497 _refine_ls_wR_factor_ref 0.1527 _refine_ls_wR_factor_gt 0.1335 _refine_ls_goodness_of_fit_ref 1.037 _refine_ls_restrained_S_all 1.035 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.10225(7) 0.08182(4) 0.59452(12) 0.1205(4) Uani 1 1 d . . . . . O1 O 0.47651(13) -0.14941(8) 0.62545(14) 0.0591(4) Uani 1 1 d . . . . . O2 O 0.34444(17) -0.25624(10) 0.29274(15) 0.0779(5) Uani 1 1 d . . . . . O3 O 0.6025(2) -0.07608(13) 0.8844(2) 0.1041(7) Uani 1 1 d . . . . . O4 O 0.4685(2) -0.08376(10) 0.98050(19) 0.0961(7) Uani 1 1 d . . . . . N1 N 0.30392(16) -0.26157(10) 0.49350(18) 0.0544(5) Uani 1 1 d . . . . . H1N H 0.327(2) -0.2509(12) 0.584(2) 0.065 Uiso 1 1 d . U . . . N2 N 0.4968(2) -0.07428(11) 0.8761(2) 0.0738(6) Uani 1 1 d . . . . . C1 C 0.3910(2) -0.09369(11) 0.6073(2) 0.0566(5) Uani 1 1 d . . . . . C2 C 0.3951(2) -0.05737(12) 0.7336(2) 0.0602(6) Uani 1 1 d . . . . . C3 C 0.3069(2) -0.00449(13) 0.7317(3) 0.0726(7) Uani 1 1 d . . . . . H3 H 0.3105 0.0177 0.8183 0.087 Uiso 1 1 calc R U . . . C4 C 0.2140(2) 0.01475(14) 0.6000(3) 0.0782(7) Uani 1 1 d . . . . . C5 C 0.2091(2) -0.01773(15) 0.4723(3) 0.0822(8) Uani 1 1 d . . . . . H5 H 0.1464 -0.0034 0.3831 0.099 Uiso 1 1 calc R U . . . C6 C 0.2971(2) -0.07179(13) 0.4755(2) 0.0702(6) Uani 1 1 d . . . . . H6 H 0.2931 -0.0935 0.3884 0.084 Uiso 1 1 calc R U . . . C7 C 0.4831(2) -0.18703(12) 0.5005(2) 0.0592(6) Uani 1 1 d . U . . . C8 C 0.5246(3) -0.13728(17) 0.3998(3) 0.0897(8) Uani 1 1 d D U . . . H8A H 0.4610 -0.1311 0.3012 0.108 Uiso 0.823(16) 1 calc R U P A 1 H8B H 0.5604 -0.0881 0.4419 0.108 Uiso 0.823(16) 1 calc R U P A 1 H8C H 0.4828 -0.1502 0.2967 0.108 Uiso 0.177(16) 1 calc R U P A 2 H8D H 0.5206 -0.0825 0.4150 0.108 Uiso 0.177(16) 1 calc R U P A 2 C9 C 0.6214(6) -0.1990(3) 0.4136(6) 0.1094(18) Uani 0.823(16) 1 d D U P A 1 H9A H 0.5954 -0.2343 0.3313 0.131 Uiso 0.823(16) 1 calc R U P A 1 H9B H 0.7041 -0.1786 0.4344 0.131 Uiso 0.823(16) 1 calc R U P A 1 C9B C 0.6558(8) -0.1708(15) 0.474(4) 0.109(8) Uani 0.177(16) 1 d D U P A 2 H9B1 H 0.6876 -0.1921 0.4056 0.131 Uiso 0.177(16) 1 calc R U P A 2 H9B2 H 0.7159 -0.1358 0.5420 0.131 Uiso 0.177(16) 1 calc R U P A 2 C10 C 0.6068(2) -0.23130(16) 0.5480(3) 0.0789(7) Uani 1 1 d D U . . . H10A H 0.6705 -0.2141 0.6405 0.095 Uiso 0.823(16) 1 calc R U P A 1 H10B H 0.5972 -0.2867 0.5465 0.095 Uiso 0.823(16) 1 calc R U P A 1 H10C H 0.6531 -0.2338 0.6535 0.095 Uiso 0.177(16) 1 calc R U P A 2 H10D H 0.5980 -0.2819 0.5043 0.095 Uiso 0.177(16) 1 calc R U P A 2 C11 C 0.3693(2) -0.23760(12) 0.4200(2) 0.0530(5) Uani 1 1 d . . . . . C12 C 0.1886(2) -0.30476(13) 0.4256(2) 0.0648(6) Uani 1 1 d . . . . . H12 H 0.1858 -0.3253 0.3328 0.078 Uiso 1 1 calc R U . . . C13 C 0.1859(3) -0.3717(2) 0.5189(4) 0.1265(13) Uani 1 1 d . . . . . H13A H 0.1930 -0.3535 0.6140 0.152 Uiso 1 1 calc R U . . . H13B H 0.2561 -0.4054 0.5339 0.152 Uiso 1 1 calc R U . . . C14 C 0.0641(5) -0.4154(3) 0.4437(7) 0.190(2) Uani 1 1 d . . . . . H14A H 0.0603 -0.4363 0.3518 0.228 Uiso 1 1 calc R U . . . H14B H 0.0619 -0.4581 0.5053 0.228 Uiso 1 1 calc R U . . . C15 C -0.0459(5) -0.3654(4) 0.4148(7) 0.181(2) Uani 1 1 d . . . . . H15A H -0.0455 -0.3473 0.5071 0.217 Uiso 1 1 calc R U . . . H15B H -0.1219 -0.3947 0.3648 0.217 Uiso 1 1 calc R U . . . C16 C -0.0435(3) -0.2975(3) 0.3216(6) 0.1607(19) Uani 1 1 d . . . . . H16A H -0.1128 -0.2636 0.3097 0.193 Uiso 1 1 calc R U . . . H16B H -0.0540 -0.3155 0.2252 0.193 Uiso 1 1 calc R U . . . C17 C 0.0784(3) -0.2533(2) 0.3904(4) 0.1136(11) Uani 1 1 d . . . . . H17A H 0.0806 -0.2135 0.3232 0.136 Uiso 1 1 calc R U . . . H17B H 0.0827 -0.2285 0.4795 0.136 Uiso 1 1 calc R U . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.0781(6) 0.0752(5) 0.2080(10) -0.0035(5) 0.0575(6) 0.0091(4) O1 0.0649(9) 0.0552(9) 0.0527(8) -0.0098(6) 0.0190(7) -0.0045(7) O2 0.1036(13) 0.0944(12) 0.0449(8) -0.0150(7) 0.0395(8) -0.0265(10) O3 0.0750(13) 0.1286(18) 0.0860(13) -0.0363(11) 0.0089(10) -0.0032(12) O4 0.1463(19) 0.0708(12) 0.0679(11) -0.0131(8) 0.0396(12) -0.0118(11) N1 0.0621(11) 0.0620(11) 0.0414(8) -0.0072(7) 0.0235(8) -0.0168(8) N2 0.0934(17) 0.0531(11) 0.0659(12) -0.0207(9) 0.0228(11) -0.0076(11) C1 0.0585(12) 0.0454(11) 0.0635(12) -0.0036(9) 0.0221(10) -0.0102(10) C2 0.0656(14) 0.0481(12) 0.0628(12) -0.0105(9) 0.0217(10) -0.0128(11) C3 0.0738(16) 0.0541(14) 0.0945(17) -0.0133(12) 0.0386(14) -0.0105(12) C4 0.0626(15) 0.0526(14) 0.118(2) -0.0040(14) 0.0347(15) -0.0067(12) C5 0.0667(16) 0.0628(16) 0.0955(18) 0.0092(13) 0.0101(13) -0.0047(13) C6 0.0733(15) 0.0619(14) 0.0619(13) -0.0010(10) 0.0132(11) -0.0072(12) C7 0.0665(13) 0.0600(13) 0.0578(11) -0.0086(9) 0.0321(10) -0.0146(10) C8 0.105(2) 0.0907(19) 0.0916(18) -0.0064(14) 0.0588(16) -0.0397(16) C9 0.098(3) 0.131(4) 0.131(4) -0.037(3) 0.080(3) -0.044(3) C9B 0.086(9) 0.142(17) 0.110(16) -0.004(12) 0.051(10) -0.039(10) C10 0.0628(15) 0.0832(17) 0.0961(18) -0.0230(13) 0.0376(13) -0.0109(13) C11 0.0645(12) 0.0565(12) 0.0425(10) -0.0019(8) 0.0263(9) -0.0056(10) C12 0.0649(14) 0.0691(14) 0.0610(12) -0.0112(10) 0.0260(10) -0.0204(11) C13 0.094(2) 0.096(2) 0.173(3) 0.035(2) 0.037(2) -0.0386(19) C14 0.121(4) 0.132(4) 0.291(7) 0.033(4) 0.056(4) -0.068(3) C15 0.108(3) 0.204(6) 0.248(6) -0.051(5) 0.088(4) -0.090(4) C16 0.065(2) 0.151(4) 0.225(5) -0.033(4) 0.016(3) -0.025(2) C17 0.0636(18) 0.100(2) 0.152(3) -0.011(2) 0.0170(18) -0.0122(16) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 C4 1.736(3) . ? O1 C1 1.351(3) . ? O1 C7 1.436(2) . ? O2 C11 1.225(2) . ? O3 N2 1.205(3) . ? O4 N2 1.222(3) . ? N1 C11 1.322(2) . ? N1 C12 1.451(3) . ? N1 H1N 0.85(2) . ? N2 C2 1.468(3) . ? C1 C6 1.383(3) . ? C1 C2 1.392(3) . ? C2 C3 1.376(3) . ? C3 C4 1.366(4) . ? C3 H3 0.9300 . ? C4 C5 1.372(4) . ? C5 C6 1.385(4) . ? C5 H5 0.9300 . ? C6 H6 0.9300 . ? C7 C11 1.525(3) . ? C7 C10 1.535(3) . ? C7 C8 1.544(3) . ? C8 C9B 1.525(3) . ? C8 C9 1.525(3) . ? C8 H8A 0.9700 . ? C8 H8B 0.9700 . ? C8 H8C 0.9700 . ? C8 H8D 0.9700 . ? C9 C10 1.525(3) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C9B C10 1.525(3) . ? C9B H9B1 0.9700 . ? C9B H9B2 0.9700 . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C10 H10C 0.9700 . ? C10 H10D 0.9700 . ? C12 C17 1.490(4) . ? C12 C13 1.498(4) . ? C12 H12 0.9800 . ? C13 C14 1.519(5) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 C15 1.481(7) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 C16 1.509(7) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 C17 1.519(5) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C1 O1 C7 120.39(16) . . ? C11 N1 C12 122.77(17) . . ? C11 N1 H1N 120.6(15) . . ? C12 N1 H1N 116.6(15) . . ? O3 N2 O4 124.0(2) . . ? O3 N2 C2 118.6(2) . . ? O4 N2 C2 117.4(2) . . ? O1 C1 C6 125.88(19) . . ? O1 C1 C2 116.77(19) . . ? C6 C1 C2 117.3(2) . . ? C3 C2 C1 122.6(2) . . ? C3 C2 N2 117.2(2) . . ? C1 C2 N2 120.2(2) . . ? C4 C3 C2 118.6(2) . . ? C4 C3 H3 120.7 . . ? C2 C3 H3 120.7 . . ? C3 C4 C5 120.6(2) . . ? C3 C4 Cl1 119.4(2) . . ? C5 C4 Cl1 119.9(2) . . ? C4 C5 C6 120.4(2) . . ? C4 C5 H5 119.8 . . ? C6 C5 H5 119.8 . . ? C1 C6 C5 120.5(2) . . ? C1 C6 H6 119.8 . . ? C5 C6 H6 119.8 . . ? O1 C7 C11 112.30(16) . . ? O1 C7 C10 109.52(18) . . ? C11 C7 C10 112.69(18) . . ? O1 C7 C8 116.64(18) . . ? C11 C7 C8 114.67(18) . . ? C10 C7 C8 88.75(19) . . ? C9B C8 C7 89.4(4) . . ? C9 C8 C7 87.9(2) . . ? C9 C8 H8A 114.0 . . ? C7 C8 H8A 114.0 . . ? C9 C8 H8B 114.0 . . ? C7 C8 H8B 114.0 . . ? H8A C8 H8B 111.2 . . ? C9B C8 H8C 113.7 . . ? C7 C8 H8C 113.7 . . ? C9B C8 H8D 113.7 . . ? C7 C8 H8D 113.7 . . ? H8C C8 H8D 111.0 . . ? C10 C9 C8 89.8(2) . . ? C10 C9 H9A 113.7 . . ? C8 C9 H9A 113.7 . . ? C10 C9 H9B 113.7 . . ? C8 C9 H9B 113.7 . . ? H9A C9 H9B 110.9 . . ? C10 C9B C8 89.8(2) . . ? C10 C9B H9B1 113.7 . . ? C8 C9B H9B1 113.7 . . ? C10 C9B H9B2 113.7 . . ? C8 C9B H9B2 113.7 . . ? H9B1 C9B H9B2 110.9 . . ? C9 C10 C7 88.2(2) . . ? C9B C10 C7 89.7(4) . . ? C9 C10 H10A 113.9 . . ? C7 C10 H10A 113.9 . . ? C9 C10 H10B 113.9 . . ? C7 C10 H10B 113.9 . . ? H10A C10 H10B 111.2 . . ? C9B C10 H10C 113.7 . . ? C7 C10 H10C 113.7 . . ? C9B C10 H10D 113.7 . . ? C7 C10 H10D 113.7 . . ? H10C C10 H10D 110.9 . . ? O2 C11 N1 122.76(19) . . ? O2 C11 C7 119.36(17) . . ? N1 C11 C7 117.83(16) . . ? N1 C12 C17 110.5(2) . . ? N1 C12 C13 111.2(2) . . ? C17 C12 C13 112.4(3) . . ? N1 C12 H12 107.5 . . ? C17 C12 H12 107.5 . . ? C13 C12 H12 107.5 . . ? C12 C13 C14 109.5(3) . . ? C12 C13 H13A 109.8 . . ? C14 C13 H13A 109.8 . . ? C12 C13 H13B 109.8 . . ? C14 C13 H13B 109.8 . . ? H13A C13 H13B 108.2 . . ? C15 C14 C13 111.6(4) . . ? C15 C14 H14A 109.3 . . ? C13 C14 H14A 109.3 . . ? C15 C14 H14B 109.3 . . ? C13 C14 H14B 109.3 . . ? H14A C14 H14B 108.0 . . ? C14 C15 C16 110.5(4) . . ? C14 C15 H15A 109.6 . . ? C16 C15 H15A 109.6 . . ? C14 C15 H15B 109.6 . . ? C16 C15 H15B 109.6 . . ? H15A C15 H15B 108.1 . . ? C15 C16 C17 111.4(4) . . ? C15 C16 H16A 109.3 . . ? C17 C16 H16A 109.3 . . ? C15 C16 H16B 109.3 . . ? C17 C16 H16B 109.3 . . ? H16A C16 H16B 108.0 . . ? C12 C17 C16 111.5(3) . . ? C12 C17 H17A 109.3 . . ? C16 C17 H17A 109.3 . . ? C12 C17 H17B 109.3 . . ? C16 C17 H17B 109.3 . . ? H17A C17 H17B 108.0 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C7 O1 C1 C6 6.0(3) . . . . ? C7 O1 C1 C2 -176.76(17) . . . . ? O1 C1 C2 C3 -174.22(19) . . . . ? C6 C1 C2 C3 3.3(3) . . . . ? O1 C1 C2 N2 6.3(3) . . . . ? C6 C1 C2 N2 -176.2(2) . . . . ? O3 N2 C2 C3 -133.9(2) . . . . ? O4 N2 C2 C3 44.3(3) . . . . ? O3 N2 C2 C1 45.6(3) . . . . ? O4 N2 C2 C1 -136.2(2) . . . . ? C1 C2 C3 C4 -2.1(3) . . . . ? N2 C2 C3 C4 177.4(2) . . . . ? C2 C3 C4 C5 -0.3(4) . . . . ? C2 C3 C4 Cl1 -179.55(17) . . . . ? C3 C4 C5 C6 1.3(4) . . . . ? Cl1 C4 C5 C6 -179.43(18) . . . . ? O1 C1 C6 C5 175.1(2) . . . . ? C2 C1 C6 C5 -2.2(3) . . . . ? C4 C5 C6 C1 0.0(4) . . . . ? C1 O1 C7 C11 -68.8(2) . . . . ? C1 O1 C7 C10 165.24(17) . . . . ? C1 O1 C7 C8 66.5(3) . . . . ? O1 C7 C8 C9B 99.9(16) . . . . ? C11 C7 C8 C9B -125.8(16) . . . . ? C10 C7 C8 C9B -11.3(16) . . . . ? O1 C7 C8 C9 128.5(4) . . . . ? C11 C7 C8 C9 -97.2(4) . . . . ? C10 C7 C8 C9 17.2(3) . . . . ? C9B C8 C9 C10 75.3(7) . . . . ? C7 C8 C9 C10 -17.4(3) . . . . ? C9 C8 C9B C10 -75.2(7) . . . . ? C7 C8 C9B C10 11.4(16) . . . . ? C8 C9 C10 C9B -75.2(7) . . . . ? C8 C9 C10 C7 17.5(3) . . . . ? C8 C9B C10 C9 75.3(7) . . . . ? C8 C9B C10 C7 -11.5(16) . . . . ? O1 C7 C10 C9 -135.2(3) . . . . ? C11 C7 C10 C9 99.1(3) . . . . ? C8 C7 C10 C9 -17.3(3) . . . . ? O1 C7 C10 C9B -106.6(16) . . . . ? C11 C7 C10 C9B 127.7(16) . . . . ? C8 C7 C10 C9B 11.3(16) . . . . ? C12 N1 C11 O2 -7.3(3) . . . . ? C12 N1 C11 C7 175.00(19) . . . . ? O1 C7 C11 O2 160.27(19) . . . . ? C10 C7 C11 O2 -75.5(3) . . . . ? C8 C7 C11 O2 24.1(3) . . . . ? O1 C7 C11 N1 -22.0(3) . . . . ? C10 C7 C11 N1 102.3(2) . . . . ? C8 C7 C11 N1 -158.1(2) . . . . ? C11 N1 C12 C17 -99.4(3) . . . . ? C11 N1 C12 C13 135.1(3) . . . . ? N1 C12 C13 C14 -179.8(3) . . . . ? C17 C12 C13 C14 55.7(4) . . . . ? C12 C13 C14 C15 -57.8(6) . . . . ? C13 C14 C15 C16 57.8(6) . . . . ? C14 C15 C16 C17 -55.0(6) . . . . ? N1 C12 C17 C16 -179.0(3) . . . . ? C13 C12 C17 C16 -54.1(4) . . . . ? C15 C16 C17 C12 53.0(5) . . . . ? _refine_diff_density_max 0.197 _refine_diff_density_min -0.228 _refine_diff_density_rms 0.033 _shelxl_version_number 2012-9 _shelx_res_file ; TITL CrystalBuilderInfo $monoclinic $P 21/c $? $colourless $ CELL 0.7107 11.688 17.404 9.965 90.00 113.76 90.00 ZERR 4 0.001 0.003 0.002 0.0 0.05 0.0 LATT 1 SYMM -X , Y+.50, -Z+.50 SFAC C H CL N O UNIT 68 84 4 8 16 DEFS 0.002 0.2 0.01 0.04 ! Global default restraint esds SIZE 0.1 0.1 0.1 TEMP 20 L.S. 10 OMIT 1 0 0 OMIT 1 1 0 OMIT 0 2 1 OMIT 0 1 1 OMIT 0 2 0 OMIT 1 2 0 OMIT -1 1 1 ACTA WPDB CONF HTAB BOND $H FMAP 2 PLAN 20 SADI C8 C9 C9 C10 C8 C9B C9B C10 DELU C7 C8 C9 C10 DELU C7 C8 C9B C10 SIMU C9 C9B WGHT 0.072500 0.385000 EXTI 0.035585 FVAR 0.73649 0.82279 CL1 3 0.102255 0.081817 0.594521 11.00000 0.07813 0.07518 = 0.20798 -0.00346 0.05753 0.00907 O1 5 0.476507 -0.149414 0.625451 11.00000 0.06492 0.05524 = 0.05273 -0.00985 0.01902 -0.00453 O2 5 0.344443 -0.256235 0.292736 11.00000 0.10358 0.09445 = 0.04492 -0.01501 0.03947 -0.02647 O3 5 0.602489 -0.076083 0.884368 11.00000 0.07497 0.12859 = 0.08601 -0.03635 0.00890 -0.00323 O4 5 0.468537 -0.083758 0.980501 11.00000 0.14635 0.07077 = 0.06788 -0.01311 0.03963 -0.01185 N1 4 0.303916 -0.261568 0.493496 11.00000 0.06215 0.06197 = 0.04145 -0.00718 0.02346 -0.01675 H1N 2 0.327198 -0.250932 0.584013 11.00000 -1.20000 N2 4 0.496771 -0.074280 0.876145 11.00000 0.09339 0.05314 = 0.06594 -0.02075 0.02277 -0.00756 C1 1 0.391030 -0.093690 0.607267 11.00000 0.05852 0.04536 = 0.06346 -0.00362 0.02210 -0.01018 C2 1 0.395118 -0.057373 0.733593 11.00000 0.06560 0.04811 = 0.06277 -0.01051 0.02166 -0.01281 C3 1 0.306921 -0.004494 0.731718 11.00000 0.07375 0.05413 = 0.09448 -0.01331 0.03864 -0.01054 AFIX 43 H3 2 0.310505 0.017652 0.818258 11.00000 -1.20000 AFIX 0 C4 1 0.213992 0.014754 0.599957 11.00000 0.06259 0.05258 = 0.11785 -0.00396 0.03473 -0.00671 C5 1 0.209139 -0.017734 0.472307 11.00000 0.06666 0.06284 = 0.09550 0.00918 0.01008 -0.00473 AFIX 43 H5 2 0.146388 -0.003364 0.383136 11.00000 -1.20000 AFIX 0 C6 1 0.297126 -0.071787 0.475479 11.00000 0.07325 0.06194 = 0.06185 -0.00105 0.01321 -0.00717 AFIX 43 H6 2 0.293053 -0.093512 0.388401 11.00000 -1.20000 AFIX 0 C7 1 0.483064 -0.187035 0.500482 11.00000 0.06646 0.05997 = 0.05780 -0.00861 0.03207 -0.01457 C8 1 0.524591 -0.137284 0.399793 11.00000 0.10516 0.09069 = 0.09160 -0.00643 0.05882 -0.03971 PART 1 AFIX 23 H8A 2 0.460991 -0.131130 0.301193 21.00000 -1.20000 H8B 2 0.560361 -0.088143 0.441896 21.00000 -1.20000 AFIX 23 PART2 H8C 2 0.482819 -0.150203 0.296654 -21.00000 -1.20000 H8D 2 0.520627 -0.082468 0.414996 -21.00000 -1.20000 AFIX 0 PART 0 PART1 C9 1 0.621401 -0.198979 0.413581 21.00000 0.09834 0.13113 = 0.13142 -0.03745 0.08040 -0.04428 AFIX 23 H9A 2 0.595447 -0.234261 0.331303 21.00000 -1.20000 H9B 2 0.704096 -0.178643 0.434409 21.00000 -1.20000 AFIX 0 PART 2 C9B 1 0.655829 -0.170803 0.473831 -21.00000 0.08623 0.14225 = 0.10971 -0.00409 0.05111 -0.03919 AFIX 23 H9B1 2 0.687616 -0.192061 0.405592 -21.00000 -1.20000 H9B2 2 0.715871 -0.135801 0.542002 -21.00000 -1.20000 AFIX 0 PART 0 C10 1 0.606769 -0.231301 0.547996 11.00000 0.06279 0.08320 = 0.09607 -0.02302 0.03761 -0.01094 PART 1 AFIX 23 H10A 2 0.670531 -0.214118 0.640494 21.00000 -1.20000 H10B 2 0.597223 -0.286700 0.546472 21.00000 -1.20000 AFIX 23 PART2 H10C 2 0.653063 -0.233819 0.653457 -21.00000 -1.20000 H10D 2 0.598031 -0.281934 0.504280 -21.00000 -1.20000 AFIX 0 PART 0 C11 1 0.369317 -0.237596 0.419975 11.00000 0.06453 0.05653 = 0.04251 -0.00192 0.02632 -0.00557 REM EXYZ C12 C12B REM PART 1 C12 1 0.188574 -0.304763 0.425578 11.00000 0.06489 0.06906 = 0.06105 -0.01118 0.02601 -0.02043 AFIX 13 H12 2 0.185797 -0.325336 0.332769 11.00000 -1.20000 AFIX 0 C13 1 0.185913 -0.371653 0.518889 11.00000 0.09389 0.09589 = 0.17347 0.03490 0.03711 -0.03862 AFIX 23 H13A 2 0.192965 -0.353516 0.613952 11.00000 -1.20000 H13B 2 0.256051 -0.405409 0.533852 11.00000 -1.20000 AFIX 0 C14 1 0.064093 -0.415390 0.443733 11.00000 0.12076 0.13244 = 0.29112 0.03314 0.05585 -0.06825 AFIX 23 H14A 2 0.060288 -0.436251 0.351761 11.00000 -1.20000 H14B 2 0.061865 -0.458050 0.505276 11.00000 -1.20000 AFIX 0 C15 1 -0.045851 -0.365398 0.414845 11.00000 0.10753 0.20403 = 0.24763 -0.05126 0.08816 -0.08954 AFIX 23 H15A 2 -0.045520 -0.347300 0.507067 11.00000 -1.20000 H15B 2 -0.121878 -0.394680 0.364810 11.00000 -1.20000 AFIX 0 C16 1 -0.043517 -0.297542 0.321650 11.00000 0.06480 0.15098 = 0.22527 -0.03257 0.01586 -0.02498 AFIX 23 H16A 2 -0.112751 -0.263577 0.309730 11.00000 -1.20000 H16B 2 -0.054007 -0.315487 0.225226 11.00000 -1.20000 AFIX 0 C17 1 0.078432 -0.253291 0.390401 11.00000 0.06357 0.10008 = 0.15189 -0.01100 0.01703 -0.01220 AFIX 23 H17A 2 0.080593 -0.213538 0.323236 11.00000 -1.20000 H17B 2 0.082698 -0.228523 0.479498 11.00000 -1.20000 AFIX 0 HKLF 4 REM CrystalBuilderInfo $monoclinic $P 21/c $? $colourless $ REM R1 = 0.0497 for 2301 Fo > 4sig(Fo) and 0.0762 for all 3381 data REM 231 parameters refined using 21 restraints END WGHT 0.0725 0.3848 REM Instructions for potential hydrogen bonds EQIV $1 x, -y-1/2, z+1/2 HTAB N1 O2_$1 EQIV $2 x, -y-1/2, z-1/2 HTAB C10 O4_$2 REM Highest difference peak 0.197, deepest hole -0.228, 1-sigma level 0.033 Q1 1 0.2898 -0.2149 0.2566 11.00000 0.05 0.20 Q2 1 0.1881 -0.3597 0.4214 11.00000 0.05 0.16 Q3 1 0.1508 -0.3385 0.5594 11.00000 0.05 0.16 Q4 1 0.6177 -0.0461 0.7998 11.00000 0.05 0.15 Q5 1 -0.0773 -0.3146 0.4358 11.00000 0.05 0.15 Q6 1 0.0218 -0.3822 0.4838 11.00000 0.05 0.14 Q7 1 0.0964 0.0957 0.4812 11.00000 0.05 0.13 Q8 1 0.0997 -0.2589 0.5351 11.00000 0.05 0.13 Q9 1 0.2143 0.0166 0.5407 11.00000 0.05 0.13 Q10 1 0.0752 -0.4775 0.4423 11.00000 0.05 0.12 Q11 1 0.3830 -0.0630 0.9216 11.00000 0.05 0.12 Q12 1 0.4327 -0.1981 0.4621 11.00000 0.05 0.11 Q13 1 -0.0453 -0.3546 0.3149 11.00000 0.05 0.10 Q14 1 0.0514 -0.1889 0.4036 11.00000 0.05 0.10 Q15 1 0.4827 -0.1586 0.4579 11.00000 0.05 0.10 Q16 1 0.2704 0.0152 0.6565 11.00000 0.05 0.09 Q17 1 0.5288 -0.2094 0.5170 11.00000 0.05 0.09 Q18 1 -0.0799 -0.2758 0.2677 11.00000 0.05 0.09 Q19 1 0.7519 -0.2346 0.4390 11.00000 0.05 0.09 Q20 1 0.5237 -0.0935 0.7397 11.00000 0.05 0.09 ; _shelx_res_checksum 63575 _database_code_depnum_ccdc_archive 'CCDC 965234' ####################################################################### # # 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_compound_2b _audit_creation_method SHELXL-2012 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C17 H20 Cl N O2' _chemical_formula_sum 'C17 H20 Cl N O2' _chemical_formula_weight 305.79 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_H-M_alt 'P -1' _space_group_name_Hall '-P 1' _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, -z' _cell_length_a 5.8800(10) _cell_length_b 9.120(2) _cell_length_c 14.895(2) _cell_angle_alpha 77.537(2) _cell_angle_beta 85.432(3) _cell_angle_gamma 77.725(3) _cell_volume 761.6(2) _cell_formula_units_Z 2 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 1844 _cell_measurement_theta_min 0.998 _cell_measurement_theta_max 26.373 _exptl_crystal_description 'squared plate' _exptl_crystal_colour colourless _exptl_crystal_density_meas ? _exptl_crystal_density_method ? _exptl_crystal_density_diffrn 1.333 _exptl_crystal_F_000 324 _exptl_transmission_factor_min ? _exptl_transmission_factor_max ? _exptl_crystal_size_max 0.560 _exptl_crystal_size_mid 0.360 _exptl_crystal_size_min 0.100 _exptl_absorpt_coefficient_mu 0.255 _shelx_estimated_absorpt_T_min 0.975 _shelx_estimated_absorpt_T_max 0.975 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.92 _exptl_absorpt_correction_T_max 0.98 _exptl_absorpt_process_details 'Scalepack (Otwinowski & Minor, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_source 'fine-focus sealed tube' _diffrn_source_type 'Nonius Kappa CCD' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius kappa-CCD diffractometer' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 9 _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 6531 _diffrn_reflns_av_unetI/netI 0.0374 _diffrn_reflns_av_R_equivalents 0.0237 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_theta_min 3.548 _diffrn_reflns_theta_max 26.338 _diffrn_reflns_theta_full 25.240 _diffrn_measured_fraction_theta_max 0.975 _diffrn_measured_fraction_theta_full 0.979 _diffrn_reflns_Laue_measured_fraction_max 0.975 _diffrn_reflns_Laue_measured_fraction_full 0.979 _diffrn_reflns_point_group_measured_fraction_max 0.975 _diffrn_reflns_point_group_measured_fraction_full 0.979 _reflns_number_total 3038 _reflns_number_gt 2393 _reflns_threshold_expression 'I > 2\s(I)' _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_max . _reflns_Friedel_fraction_full . _reflns_special_details ; Reflections were merged by SHELXL according to the crystal class for the calculation of statistics and refinement. _reflns_Friedel_fraction is defined as the number of unique Friedel pairs measured divided by the number that would be possible theoretically, ignoring centric projections and systematic absences. ; _computing_data_collection 'DENZO (Otwinowski & Minor, 1997); COLLECT (Nonius B.V., 1999)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997); COLLECT (Nonius B.V., 1999)' _computing_data_reduction 'SCALEPACK (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-2012 (Sheldrick, 2012);CRYSTALBUILDER (Welter, 2006)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material 'SHELXL97 (Sheldrick, 2008)' _refine_special_details ; ? ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; w=1/[\s^2^(Fo^2^)+(0.0513P)^2^+0.2838P] where P=(Fo^2^+2Fc^2^)/3 ; _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef . _refine_ls_number_reflns 3035 _refine_ls_number_parameters 190 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0615 _refine_ls_R_factor_gt 0.0449 _refine_ls_wR_factor_ref 0.1217 _refine_ls_wR_factor_gt 0.1098 _refine_ls_goodness_of_fit_ref 1.017 _refine_ls_restrained_S_all 1.017 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.74077(10) 0.24929(7) -0.08307(4) 0.0695(2) Uani 1 1 d . . . . . O1 O -0.1526(2) 0.12381(15) 0.33810(10) 0.0556(4) Uani 1 1 d . . . . . O3 O -0.0024(2) 0.29757(15) 0.11380(9) 0.0509(3) Uani 1 1 d . . . . . N2 N 0.1699(2) 0.05113(15) 0.25050(10) 0.0391(3) Uani 1 1 d . . . . . C1 C -0.0737(3) 0.3070(2) 0.20663(13) 0.0445(4) Uani 1 1 d . . . . . C2 C -0.0264(3) 0.1517(2) 0.27074(12) 0.0409(4) Uani 1 1 d . . . . . C3 C 0.3165(3) 0.09846(18) 0.17363(12) 0.0370(4) Uani 1 1 d . . . . . C4 C 0.5471(3) 0.0268(2) 0.16211(13) 0.0446(4) Uani 1 1 d . . . . . H4 H 0.6154 -0.0529 0.2082 0.053 Uiso 1 1 calc R U . . . C5 C 0.6768(3) 0.0721(2) 0.08332(13) 0.0485(5) Uani 1 1 d . . . . . H5 H 0.8302 0.0221 0.0759 0.058 Uiso 1 1 calc R U . . . C6 C 0.5773(3) 0.1915(2) 0.01612(13) 0.0469(4) Uani 1 1 d . . . . . C7 C 0.3514(3) 0.2688(2) 0.02649(13) 0.0490(5) Uani 1 1 d . . . . . H7 H 0.2866 0.3513 -0.0187 0.059 Uiso 1 1 calc R U . . . C8 C 0.2234(3) 0.2215(2) 0.10512(12) 0.0409(4) Uani 1 1 d . . . . . C9 C -0.3226(3) 0.3993(2) 0.21057(17) 0.0584(6) Uani 1 1 d . . . . . H9A H -0.3947 0.4324 0.1513 0.070 Uiso 1 1 calc R U . . . H9B H -0.4234 0.3497 0.2565 0.070 Uiso 1 1 calc R U . . . C10 C -0.2300(4) 0.5238(3) 0.24069(18) 0.0726(7) Uani 1 1 d . . . . . H10A H -0.2504 0.6195 0.1957 0.087 Uiso 1 1 calc R U . . . H10B H -0.2903 0.5413 0.3008 0.087 Uiso 1 1 calc R U . . . C11 C 0.0158(3) 0.4317(2) 0.24170(17) 0.0566(5) Uani 1 1 d . . . . . H11A H 0.0789 0.3972 0.3026 0.068 Uiso 1 1 calc R U . . . H11B H 0.1227 0.4813 0.1987 0.068 Uiso 1 1 calc R U . . . C12 C 0.2459(3) -0.09614(18) 0.31563(11) 0.0380(4) Uani 1 1 d . . . . . H12 H 0.3788 -0.1536 0.2854 0.046 Uiso 1 1 calc R U . . . C13 C 0.0618(3) -0.1957(2) 0.33538(14) 0.0469(4) Uani 1 1 d . . . . . H13A H -0.0757 -0.1429 0.3644 0.056 Uiso 1 1 calc R U . . . H13B H 0.0171 -0.2142 0.2782 0.056 Uiso 1 1 calc R U . . . C14 C 0.1590(4) -0.3476(2) 0.39851(14) 0.0516(5) Uani 1 1 d . . . . . H14A H 0.0388 -0.4081 0.4135 0.062 Uiso 1 1 calc R U . . . H14B H 0.2869 -0.4044 0.3668 0.062 Uiso 1 1 calc R U . . . C15 C 0.2441(4) -0.3230(2) 0.48658(14) 0.0554(5) Uani 1 1 d . . . . . H15A H 0.1136 -0.2737 0.5208 0.066 Uiso 1 1 calc R U . . . H15B H 0.3093 -0.4215 0.5244 0.066 Uiso 1 1 calc R U . . . C16 C 0.4269(4) -0.2249(2) 0.46654(14) 0.0551(5) Uani 1 1 d . . . . . H16A H 0.5640 -0.2789 0.4379 0.066 Uiso 1 1 calc R U . . . H16B H 0.4720 -0.2067 0.5238 0.066 Uiso 1 1 calc R U . . . C17 C 0.3357(3) -0.0720(2) 0.40306(13) 0.0470(4) Uani 1 1 d . . . . . H17A H 0.2109 -0.0124 0.4347 0.056 Uiso 1 1 calc R U . . . H17B H 0.4597 -0.0147 0.3874 0.056 Uiso 1 1 calc R U . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.0640(4) 0.0825(4) 0.0523(3) 0.0021(3) 0.0200(2) -0.0176(3) O1 0.0531(8) 0.0501(8) 0.0570(8) -0.0086(6) 0.0199(6) -0.0060(6) O3 0.0368(7) 0.0550(8) 0.0520(8) 0.0024(6) -0.0012(6) -0.0032(6) N2 0.0387(7) 0.0337(7) 0.0411(8) -0.0035(6) 0.0073(6) -0.0060(6) C1 0.0336(9) 0.0388(9) 0.0570(11) -0.0046(8) 0.0053(8) -0.0058(7) C2 0.0387(9) 0.0391(9) 0.0448(10) -0.0093(7) 0.0049(7) -0.0089(7) C3 0.0369(8) 0.0358(8) 0.0387(9) -0.0058(7) 0.0036(7) -0.0115(7) C4 0.0384(9) 0.0406(9) 0.0493(10) -0.0015(8) 0.0033(8) -0.0057(7) C5 0.0386(9) 0.0497(10) 0.0535(11) -0.0070(9) 0.0091(8) -0.0087(8) C6 0.0471(10) 0.0534(11) 0.0403(10) -0.0053(8) 0.0093(8) -0.0188(8) C7 0.0470(10) 0.0524(11) 0.0425(10) 0.0027(8) -0.0003(8) -0.0121(8) C8 0.0349(8) 0.0420(9) 0.0441(10) -0.0049(8) -0.0007(7) -0.0081(7) C9 0.0348(9) 0.0529(12) 0.0763(14) -0.0002(10) 0.0079(9) -0.0010(8) C10 0.0680(14) 0.0707(15) 0.0739(16) -0.0318(12) -0.0095(12) 0.0176(12) C11 0.0508(11) 0.0421(10) 0.0766(14) -0.0125(10) 0.0080(10) -0.0124(9) C12 0.0402(9) 0.0326(8) 0.0385(9) -0.0042(7) 0.0064(7) -0.0076(7) C13 0.0511(11) 0.0419(10) 0.0499(11) -0.0076(8) 0.0005(8) -0.0170(8) C14 0.0582(11) 0.0370(9) 0.0587(12) -0.0059(8) 0.0109(9) -0.0165(8) C15 0.0678(13) 0.0472(11) 0.0442(11) 0.0016(9) 0.0061(9) -0.0104(9) C16 0.0613(12) 0.0546(12) 0.0482(11) -0.0065(9) -0.0076(9) -0.0108(9) C17 0.0507(10) 0.0422(10) 0.0504(11) -0.0087(8) -0.0021(8) -0.0147(8) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 C6 1.7431(18) . ? O1 C2 1.214(2) . ? O3 C8 1.371(2) . ? O3 C1 1.428(2) . ? N2 C2 1.370(2) . ? N2 C3 1.424(2) . ? N2 C12 1.482(2) . ? C1 C2 1.512(2) . ? C1 C9 1.529(2) . ? C1 C11 1.549(3) . ? C3 C4 1.389(2) . ? C3 C8 1.391(2) . ? C4 C5 1.383(2) . ? C4 H4 0.9300 . ? C5 C6 1.372(3) . ? C5 H5 0.9300 . ? C6 C7 1.379(3) . ? C7 C8 1.380(2) . ? C7 H7 0.9300 . ? C9 C10 1.519(3) . ? C9 H9A 0.9700 . ? C9 H9B 0.9700 . ? C10 C11 1.509(3) . ? C10 H10A 0.9700 . ? C10 H10B 0.9700 . ? C11 H11A 0.9700 . ? C11 H11B 0.9700 . ? C12 C17 1.519(3) . ? C12 C13 1.528(2) . ? C12 H12 0.9800 . ? C13 C14 1.522(3) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 C15 1.517(3) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 C16 1.512(3) . ? C15 H15A 0.9700 . ? C15 H15B 0.9700 . ? C16 C17 1.523(3) . ? C16 H16A 0.9700 . ? C16 H16B 0.9700 . ? C17 H17A 0.9700 . ? C17 H17B 0.9700 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C8 O3 C1 113.09(13) . . ? C2 N2 C3 119.28(14) . . ? C2 N2 C12 119.89(13) . . ? C3 N2 C12 120.23(13) . . ? O3 C1 C2 111.95(14) . . ? O3 C1 C9 110.22(16) . . ? C2 C1 C9 115.85(15) . . ? O3 C1 C11 113.94(15) . . ? C2 C1 C11 113.40(17) . . ? C9 C1 C11 89.77(15) . . ? O1 C2 N2 123.37(16) . . ? O1 C2 C1 120.33(15) . . ? N2 C2 C1 116.21(14) . . ? C4 C3 C8 117.82(15) . . ? C4 C3 N2 123.72(15) . . ? C8 C3 N2 118.45(15) . . ? C5 C4 C3 121.09(17) . . ? C5 C4 H4 119.5 . . ? C3 C4 H4 119.5 . . ? C6 C5 C4 119.44(17) . . ? C6 C5 H5 120.3 . . ? C4 C5 H5 120.3 . . ? C5 C6 C7 121.13(16) . . ? C5 C6 Cl1 119.52(14) . . ? C7 C6 Cl1 119.33(15) . . ? C6 C7 C8 118.81(17) . . ? C6 C7 H7 120.6 . . ? C8 C7 H7 120.6 . . ? O3 C8 C7 118.22(16) . . ? O3 C8 C3 120.12(15) . . ? C7 C8 C3 121.65(16) . . ? C10 C9 C1 89.41(15) . . ? C10 C9 H9A 113.7 . . ? C1 C9 H9A 113.7 . . ? C10 C9 H9B 113.7 . . ? C1 C9 H9B 113.7 . . ? H9A C9 H9B 111.0 . . ? C11 C10 C9 91.65(16) . . ? C11 C10 H10A 113.3 . . ? C9 C10 H10A 113.3 . . ? C11 C10 H10B 113.3 . . ? C9 C10 H10B 113.3 . . ? H10A C10 H10B 110.7 . . ? C10 C11 C1 89.06(16) . . ? C10 C11 H11A 113.8 . . ? C1 C11 H11A 113.8 . . ? C10 C11 H11B 113.8 . . ? C1 C11 H11B 113.8 . . ? H11A C11 H11B 111.0 . . ? N2 C12 C17 111.62(14) . . ? N2 C12 C13 113.30(14) . . ? C17 C12 C13 112.36(15) . . ? N2 C12 H12 106.3 . . ? C17 C12 H12 106.3 . . ? C13 C12 H12 106.3 . . ? C14 C13 C12 109.72(15) . . ? C14 C13 H13A 109.7 . . ? C12 C13 H13A 109.7 . . ? C14 C13 H13B 109.7 . . ? C12 C13 H13B 109.7 . . ? H13A C13 H13B 108.2 . . ? C15 C14 C13 111.30(16) . . ? C15 C14 H14A 109.4 . . ? C13 C14 H14A 109.4 . . ? C15 C14 H14B 109.4 . . ? C13 C14 H14B 109.4 . . ? H14A C14 H14B 108.0 . . ? C16 C15 C14 111.29(16) . . ? C16 C15 H15A 109.4 . . ? C14 C15 H15A 109.4 . . ? C16 C15 H15B 109.4 . . ? C14 C15 H15B 109.4 . . ? H15A C15 H15B 108.0 . . ? C15 C16 C17 111.12(17) . . ? C15 C16 H16A 109.4 . . ? C17 C16 H16A 109.4 . . ? C15 C16 H16B 109.4 . . ? C17 C16 H16B 109.4 . . ? H16A C16 H16B 108.0 . . ? C12 C17 C16 110.87(15) . . ? C12 C17 H17A 109.5 . . ? C16 C17 H17A 109.5 . . ? C12 C17 H17B 109.5 . . ? C16 C17 H17B 109.5 . . ? H17A C17 H17B 108.1 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C8 O3 C1 C2 -52.1(2) . . . . ? C8 O3 C1 C9 177.38(15) . . . . ? C8 O3 C1 C11 78.24(18) . . . . ? C3 N2 C2 O1 -175.35(17) . . . . ? C12 N2 C2 O1 -4.2(3) . . . . ? C3 N2 C2 C1 1.3(2) . . . . ? C12 N2 C2 C1 172.50(15) . . . . ? O3 C1 C2 O1 -148.71(17) . . . . ? C9 C1 C2 O1 -21.2(3) . . . . ? C11 C1 C2 O1 80.7(2) . . . . ? O3 C1 C2 N2 34.5(2) . . . . ? C9 C1 C2 N2 162.03(17) . . . . ? C11 C1 C2 N2 -96.14(19) . . . . ? C2 N2 C3 C4 160.57(17) . . . . ? C12 N2 C3 C4 -10.6(3) . . . . ? C2 N2 C3 C8 -20.7(2) . . . . ? C12 N2 C3 C8 168.20(15) . . . . ? C8 C3 C4 C5 -2.7(3) . . . . ? N2 C3 C4 C5 176.05(17) . . . . ? C3 C4 C5 C6 1.1(3) . . . . ? C4 C5 C6 C7 1.1(3) . . . . ? C4 C5 C6 Cl1 179.74(15) . . . . ? C5 C6 C7 C8 -1.7(3) . . . . ? Cl1 C6 C7 C8 179.73(15) . . . . ? C1 O3 C8 C7 -146.30(17) . . . . ? C1 O3 C8 C3 34.9(2) . . . . ? C6 C7 C8 O3 -178.79(17) . . . . ? C6 C7 C8 C3 0.0(3) . . . . ? C4 C3 C8 O3 -179.08(16) . . . . ? N2 C3 C8 O3 2.1(3) . . . . ? C4 C3 C8 C7 2.2(3) . . . . ? N2 C3 C8 C7 -176.65(16) . . . . ? O3 C1 C9 C10 -113.09(18) . . . . ? C2 C1 C9 C10 118.51(19) . . . . ? C11 C1 C9 C10 2.44(17) . . . . ? C1 C9 C10 C11 -2.50(18) . . . . ? C9 C10 C11 C1 2.47(17) . . . . ? O3 C1 C11 C10 109.66(18) . . . . ? C2 C1 C11 C10 -120.71(18) . . . . ? C9 C1 C11 C10 -2.45(17) . . . . ? C2 N2 C12 C17 -69.7(2) . . . . ? C3 N2 C12 C17 101.36(18) . . . . ? C2 N2 C12 C13 58.3(2) . . . . ? C3 N2 C12 C13 -130.60(16) . . . . ? N2 C12 C13 C14 176.94(14) . . . . ? C17 C12 C13 C14 -55.4(2) . . . . ? C12 C13 C14 C15 56.0(2) . . . . ? C13 C14 C15 C16 -57.3(2) . . . . ? C14 C15 C16 C17 56.1(2) . . . . ? N2 C12 C17 C16 -176.47(14) . . . . ? C13 C12 C17 C16 55.0(2) . . . . ? C15 C16 C17 C12 -54.7(2) . . . . ? _refine_diff_density_max 0.196 _refine_diff_density_min -0.320 _refine_diff_density_rms 0.036 _shelxl_version_number 2012-9 _shelx_res_file ; TITL CrystalBuilderInfo $triclinic $P -1 $? $colourless $ CELL 0.71069 5.880 9.120 14.895 77.537 85.432 77.725 ZERR 2 0.001 0.002 0.002 0.002 0.003 0.003 LATT 1 SFAC C H N O CL UNIT 34 40 2 4 2 CONF HTAB BOND $H DEFS 0.002 0.2 0.01 0.05 ! Global default restraint esds SIZE 0.1 0.1 0.1 TEMP 20 ACTA MERG 2 OMIT 0 1 2 OMIT 0 1 0 OMIT 0 0 1 L.S. 13 WPDB FMAP 2 PLAN 25 WGHT 0.051300 0.283800 FVAR 1.72577 CL1 5 0.740773 0.249291 -0.083070 11.00000 0.06401 0.08251 = 0.05233 0.00208 0.01998 -0.01762 O1 4 -0.152592 0.123814 0.338103 11.00000 0.05311 0.05007 = 0.05703 -0.00858 0.01988 -0.00599 O3 4 -0.002411 0.297575 0.113799 11.00000 0.03684 0.05496 = 0.05204 0.00244 -0.00116 -0.00323 N2 3 0.169897 0.051131 0.250499 11.00000 0.03865 0.03366 = 0.04109 -0.00347 0.00726 -0.00596 C1 1 -0.073728 0.307016 0.206631 11.00000 0.03359 0.03880 = 0.05698 -0.00457 0.00532 -0.00577 C2 1 -0.026353 0.151727 0.270742 11.00000 0.03865 0.03907 = 0.04485 -0.00925 0.00493 -0.00890 C3 1 0.316521 0.098463 0.173630 11.00000 0.03687 0.03576 = 0.03874 -0.00579 0.00362 -0.01145 C4 1 0.547114 0.026814 0.162110 11.00000 0.03838 0.04065 = 0.04929 -0.00154 0.00326 -0.00566 AFIX 43 H4 2 0.615390 -0.052935 0.208153 11.00000 -1.20000 AFIX 0 C5 1 0.676808 0.072110 0.083318 11.00000 0.03863 0.04972 = 0.05353 -0.00696 0.00911 -0.00871 AFIX 43 H5 2 0.830230 0.022080 0.075944 11.00000 -1.20000 AFIX 0 C6 1 0.577265 0.191463 0.016120 11.00000 0.04715 0.05338 = 0.04030 -0.00531 0.00933 -0.01880 C7 1 0.351444 0.268772 0.026491 11.00000 0.04700 0.05243 = 0.04253 0.00270 -0.00033 -0.01211 AFIX 43 H7 2 0.286579 0.351275 -0.018695 11.00000 -1.20000 AFIX 0 C8 1 0.223381 0.221543 0.105122 11.00000 0.03486 0.04202 = 0.04405 -0.00485 -0.00067 -0.00810 C9 1 -0.322572 0.399341 0.210568 11.00000 0.03480 0.05292 = 0.07632 -0.00018 0.00785 -0.00104 AFIX 23 H9A 2 -0.394709 0.432361 0.151285 11.00000 -1.20000 H9B 2 -0.423405 0.349661 0.256512 11.00000 -1.20000 AFIX 0 C10 1 -0.229999 0.523821 0.240690 11.00000 0.06798 0.07073 = 0.07391 -0.03181 -0.00952 0.01762 AFIX 23 H10A 2 -0.250414 0.619524 0.195714 11.00000 -1.20000 H10B 2 -0.290321 0.541322 0.300836 11.00000 -1.20000 AFIX 0 C11 1 0.015787 0.431722 0.241698 11.00000 0.05085 0.04214 = 0.07655 -0.01247 0.00798 -0.01240 AFIX 23 H11A 2 0.078883 0.397193 0.302622 11.00000 -1.20000 H11B 2 0.122716 0.481262 0.198733 11.00000 -1.20000 AFIX 0 C12 1 0.245850 -0.096136 0.315634 11.00000 0.04022 0.03265 = 0.03851 -0.00423 0.00643 -0.00763 AFIX 13 H12 2 0.378785 -0.153608 0.285382 11.00000 -1.20000 AFIX 0 C13 1 0.061789 -0.195681 0.335381 11.00000 0.05108 0.04195 = 0.04994 -0.00756 0.00048 -0.01701 AFIX 23 H13A 2 -0.075705 -0.142901 0.364406 11.00000 -1.20000 H13B 2 0.017134 -0.214216 0.278151 11.00000 -1.20000 AFIX 0 C14 1 0.158972 -0.347631 0.398509 11.00000 0.05816 0.03704 = 0.05869 -0.00592 0.01085 -0.01651 AFIX 23 H14A 2 0.038773 -0.408099 0.413471 11.00000 -1.20000 H14B 2 0.286946 -0.404411 0.366788 11.00000 -1.20000 AFIX 0 C15 1 0.244147 -0.323021 0.486581 11.00000 0.06777 0.04716 = 0.04422 0.00160 0.00608 -0.01038 AFIX 23 H15A 2 0.113592 -0.273702 0.520781 11.00000 -1.20000 H15B 2 0.309327 -0.421503 0.524430 11.00000 -1.20000 AFIX 0 C16 1 0.426894 -0.224907 0.466537 11.00000 0.06132 0.05458 = 0.04819 -0.00647 -0.00758 -0.01081 AFIX 23 H16A 2 0.563976 -0.278888 0.437919 11.00000 -1.20000 H16B 2 0.471958 -0.206721 0.523798 11.00000 -1.20000 AFIX 0 C17 1 0.335683 -0.071974 0.403057 11.00000 0.05067 0.04221 = 0.05042 -0.00874 -0.00211 -0.01469 AFIX 23 H17A 2 0.210936 -0.012403 0.434672 11.00000 -1.20000 H17B 2 0.459705 -0.014737 0.387408 11.00000 -1.20000 AFIX 0 HKLF 4 REM CrystalBuilderInfo $triclinic $P -1 $? $colourless $ REM R1 = 0.0449 for 2393 Fo > 4sig(Fo) and 0.0615 for all 3035 data REM 190 parameters refined using 0 restraints END WGHT 0.0511 0.2846 REM Instructions for potential hydrogen bonds EQIV $1 -x+1, -y+1, -z HTAB C11 Cl1_$1 HTAB C13 O1 HTAB C17 O1 REM Highest difference peak 0.196, deepest hole -0.320, 1-sigma level 0.036 Q1 1 -0.0326 0.2358 0.2355 11.00000 0.05 0.20 Q2 1 0.1968 0.4284 0.2597 11.00000 0.05 0.16 Q3 1 0.1425 -0.1470 0.3287 11.00000 0.05 0.16 Q4 1 0.6113 0.0904 0.0364 11.00000 0.05 0.15 Q5 1 0.7490 0.3293 -0.0596 11.00000 0.05 0.15 Q6 1 0.4635 0.1926 0.0075 11.00000 0.05 0.14 Q7 1 0.2841 0.2077 0.0592 11.00000 0.05 0.14 Q8 1 0.2483 0.0781 0.2192 11.00000 0.05 0.14 Q9 1 0.3007 0.2675 0.0817 11.00000 0.05 0.13 Q10 1 0.4237 0.0845 0.1768 11.00000 0.05 0.13 Q11 1 0.4914 0.2518 0.0328 11.00000 0.05 0.13 Q12 1 -0.1910 0.3446 0.2110 11.00000 0.05 0.13 Q13 1 -0.3242 0.4364 0.3182 11.00000 0.05 0.12 Q14 1 0.4176 0.0331 0.1588 11.00000 0.05 0.12 Q15 1 0.2667 0.1427 0.1401 11.00000 0.05 0.12 Q16 1 0.6460 0.1917 -0.0365 11.00000 0.05 0.12 Q17 1 -0.2737 0.6374 0.2635 11.00000 0.05 0.12 Q18 1 0.6443 0.1143 -0.0739 11.00000 0.05 0.11 Q19 1 -0.0496 0.2944 0.1621 11.00000 0.05 0.11 Q20 1 0.5556 -0.1041 0.1813 11.00000 0.05 0.11 Q21 1 0.1292 -0.2594 0.3717 11.00000 0.05 0.11 Q22 1 0.6212 0.3854 -0.1404 11.00000 0.05 0.11 Q23 1 -0.0002 -0.1615 0.3751 11.00000 0.05 0.11 Q24 1 0.6101 -0.2318 0.5018 11.00000 0.05 0.11 Q25 1 -0.0041 -0.2542 0.5034 11.00000 0.05 0.11 ; _shelx_res_checksum 39846 _database_code_depnum_ccdc_archive 'CCDC 965235' ####################################################################### # # 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_compound_2p _audit_creation_method SHELXL-2012 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C19 H19 Cl2 N O2' _chemical_formula_sum 'C19 H19 Cl2 N O2' _chemical_formula_weight 364.25 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_H-M_alt 'P 21/c' _space_group_name_Hall '-P 2ybc' _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 5.9540(10) _cell_length_b 8.628(2) _cell_length_c 34.703(5) _cell_angle_alpha 90 _cell_angle_beta 93.476(2) _cell_angle_gamma 90 _cell_volume 1779.5(6) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2668 _cell_measurement_theta_min 0.998 _cell_measurement_theta_max 26.373 _exptl_crystal_description cube _exptl_crystal_colour orange _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.30 _exptl_crystal_size_min 0.30 _exptl_crystal_density_meas ? _exptl_crystal_density_method ? _exptl_crystal_density_diffrn 1.360 _exptl_crystal_F_000 760 _exptl_transmission_factor_min ? _exptl_transmission_factor_max ? _exptl_absorpt_coefficient_mu 0.376 _shelx_estimated_absorpt_T_min 0.963 _shelx_estimated_absorpt_T_max 0.963 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.78 _exptl_absorpt_correction_T_max 0.89 _exptl_absorpt_process_details 'Scalepack (Otwinowski & Minor, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_source 'fine-focus sealed tube' _diffrn_source_type 'Nonius Kappa CCD' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius kappa-CCD diffractometer' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 9 _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 9987 _diffrn_reflns_av_unetI/netI 0.0409 _diffrn_reflns_av_R_equivalents 0.0279 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_l_min -42 _diffrn_reflns_limit_l_max 42 _diffrn_reflns_theta_min 3.333 _diffrn_reflns_theta_max 26.235 _diffrn_reflns_theta_full 25.242 _diffrn_measured_fraction_theta_max 0.953 _diffrn_measured_fraction_theta_full 0.959 _diffrn_reflns_Laue_measured_fraction_max 0.953 _diffrn_reflns_Laue_measured_fraction_full 0.959 _diffrn_reflns_point_group_measured_fraction_max 0.953 _diffrn_reflns_point_group_measured_fraction_full 0.959 _reflns_number_total 3429 _reflns_number_gt 2423 _reflns_threshold_expression 'I > 2\s(I)' _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_max . _reflns_Friedel_fraction_full . _reflns_special_details ; Reflections were merged by SHELXL according to the crystal class for the calculation of statistics and refinement. _reflns_Friedel_fraction is defined as the number of unique Friedel pairs measured divided by the number that would be possible theoretically, ignoring centric projections and systematic absences. ; _computing_data_collection 'DENZO (Otwinowski & Minor, 1997); COLLECT (Nonius B.V., 1999)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997); COLLECT (Nonius B.V., 1999)' _computing_data_reduction 'SCALEPACK (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-2012 (Sheldrick, 2012);CRYSTALBUILDER (Welter, 2006)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material 'SHELXL97 (Sheldrick, 2008)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. Nine OMITted reflections due to beamstop shading. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; w=1/[\s^2^(Fo^2^)+(0.0509P)^2^+0.8320P] where P=(Fo^2^+2Fc^2^)/3 ; _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.024(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3420 _refine_ls_number_parameters 221 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0773 _refine_ls_R_factor_gt 0.0512 _refine_ls_wR_factor_ref 0.1357 _refine_ls_wR_factor_gt 0.1199 _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_restrained_S_all 1.032 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl -0.07634(14) 0.25857(11) 0.47975(3) 0.0940(4) Uani 1 1 d . . . . . Cl2 Cl -0.05388(16) -0.02815(12) 0.19294(2) 0.1016(4) Uani 1 1 d . . . . . O1 O 0.5879(3) -0.0608(2) 0.44273(4) 0.0577(5) Uani 1 1 d . . . . . O2 O 0.8086(3) -0.1508(2) 0.35285(5) 0.0692(5) Uani 1 1 d . . . . . N1 N 0.5461(3) 0.0274(2) 0.36632(5) 0.0504(5) Uani 1 1 d . . . . . C1 C 0.6596(4) -0.1713(3) 0.41469(6) 0.0488(6) Uani 1 1 d . . . . . H1 H 0.8134 -0.2004 0.4235 0.059 Uiso 1 1 calc R U . . . C2 C 0.6781(4) -0.0985(3) 0.37526(6) 0.0502(6) Uani 1 1 d . . . . . C3 C 0.3914(4) 0.0829(3) 0.39250(6) 0.0465(5) Uani 1 1 d . . . . . C4 C 0.2155(4) 0.1816(3) 0.38137(7) 0.0591(6) Uani 1 1 d . . . . . H4 H 0.1947 0.2122 0.3557 0.071 Uiso 1 1 calc R U . . . C5 C 0.0716(5) 0.2348(3) 0.40792(8) 0.0667(7) Uani 1 1 d . . . . . H5 H -0.0465 0.3006 0.4002 0.080 Uiso 1 1 calc R U . . . C6 C 0.1032(4) 0.1901(3) 0.44601(8) 0.0604(7) Uani 1 1 d . . . . . C7 C 0.2738(4) 0.0902(3) 0.45771(7) 0.0575(6) Uani 1 1 d . . . . . H7 H 0.2932 0.0593 0.4834 0.069 Uiso 1 1 calc R U . . . C8 C 0.4162(4) 0.0366(3) 0.43061(6) 0.0483(6) Uani 1 1 d . . . . . C9 C 0.5209(4) -0.3229(3) 0.41505(7) 0.0515(6) Uani 1 1 d . . . . . C10 C 0.2784(5) -0.2991(4) 0.40134(12) 0.1014(12) Uani 1 1 d . . . . . H10A H 0.2704 -0.2665 0.3748 0.152 Uiso 1 1 calc R U . . . H10B H 0.2128 -0.2210 0.4169 0.152 Uiso 1 1 calc R U . . . H10C H 0.1975 -0.3946 0.4036 0.152 Uiso 1 1 calc R U . . . C11 C 0.5275(7) -0.3832(4) 0.45636(9) 0.1032(12) Uani 1 1 d . . . . . H11A H 0.4485 -0.4801 0.4570 0.155 Uiso 1 1 calc R U . . . H11B H 0.4570 -0.3093 0.4724 0.155 Uiso 1 1 calc R U . . . H11C H 0.6810 -0.3981 0.4657 0.155 Uiso 1 1 calc R U . . . C12 C 0.6264(6) -0.4431(4) 0.39011(12) 0.0970(11) Uani 1 1 d . . . . . H12A H 0.5540 -0.5412 0.3934 0.145 Uiso 1 1 calc R U . . . H12B H 0.7837 -0.4522 0.3976 0.145 Uiso 1 1 calc R U . . . H12C H 0.6084 -0.4121 0.3635 0.145 Uiso 1 1 calc R U . . . C13 C 0.5780(4) 0.1100(3) 0.33015(7) 0.0603(7) Uani 1 1 d . . . . . H13A H 0.7309 0.0924 0.3230 0.072 Uiso 1 1 calc R U . . . H13B H 0.5620 0.2202 0.3348 0.072 Uiso 1 1 calc R U . . . C14 C 0.4200(4) 0.0660(3) 0.29643(6) 0.0496(6) Uani 1 1 d . . . . . C15 C 0.2369(4) -0.0308(3) 0.29919(7) 0.0572(6) Uani 1 1 d . . . . . H15 H 0.2111 -0.0767 0.3228 0.069 Uiso 1 1 calc R U . . . C16 C 0.0922(5) -0.0605(3) 0.26764(7) 0.0631(7) Uani 1 1 d . . . . . H16 H -0.0311 -0.1254 0.2699 0.076 Uiso 1 1 calc R U . . . C17 C 0.1315(5) 0.0065(3) 0.23287(7) 0.0609(7) Uani 1 1 d . . . . . C18 C 0.3116(5) 0.1016(4) 0.22903(7) 0.0714(8) Uani 1 1 d . . . . . H18 H 0.3368 0.1462 0.2053 0.086 Uiso 1 1 calc R U . . . C19 C 0.4556(5) 0.1305(3) 0.26068(7) 0.0657(7) Uani 1 1 d . . . . . H19 H 0.5793 0.1947 0.2581 0.079 Uiso 1 1 calc R U . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.0937(6) 0.0942(6) 0.0967(6) -0.0208(5) 0.0276(4) 0.0339(5) Cl2 0.1206(7) 0.1229(8) 0.0579(5) -0.0103(5) -0.0212(4) -0.0158(6) O1 0.0659(10) 0.0663(11) 0.0399(9) -0.0051(8) -0.0055(7) 0.0249(9) O2 0.0623(11) 0.0855(14) 0.0624(11) -0.0026(10) 0.0248(9) 0.0091(10) N1 0.0541(11) 0.0588(13) 0.0386(10) 0.0050(9) 0.0056(8) 0.0017(9) C1 0.0433(12) 0.0600(14) 0.0430(12) -0.0046(11) 0.0027(9) 0.0141(11) C2 0.0437(12) 0.0602(15) 0.0466(13) -0.0027(11) 0.0028(10) 0.0006(11) C3 0.0517(12) 0.0440(13) 0.0433(13) 0.0017(10) -0.0011(9) 0.0051(10) C4 0.0705(16) 0.0525(14) 0.0530(15) 0.0039(12) -0.0076(12) 0.0088(13) C5 0.0647(16) 0.0555(16) 0.079(2) -0.0025(14) -0.0070(13) 0.0216(13) C6 0.0620(15) 0.0538(15) 0.0660(17) -0.0114(13) 0.0081(12) 0.0140(12) C7 0.0723(16) 0.0557(15) 0.0448(13) -0.0046(11) 0.0057(11) 0.0148(13) C8 0.0539(13) 0.0480(13) 0.0423(12) -0.0019(10) -0.0013(10) 0.0116(11) C9 0.0481(12) 0.0569(14) 0.0502(13) 0.0002(11) 0.0092(10) 0.0084(11) C10 0.0591(18) 0.075(2) 0.167(4) 0.018(2) -0.023(2) -0.0067(16) C11 0.148(3) 0.093(3) 0.070(2) 0.0194(19) 0.013(2) -0.008(2) C12 0.108(2) 0.066(2) 0.123(3) -0.0219(19) 0.050(2) 0.0014(18) C13 0.0666(15) 0.0672(16) 0.0474(14) 0.0093(12) 0.0071(11) -0.0101(13) C14 0.0570(13) 0.0508(13) 0.0417(13) 0.0031(10) 0.0087(10) 0.0004(11) C15 0.0666(15) 0.0632(16) 0.0422(14) 0.0093(11) 0.0069(11) -0.0088(13) C16 0.0677(16) 0.0663(17) 0.0556(16) -0.0006(13) 0.0065(12) -0.0102(13) C17 0.0758(17) 0.0623(16) 0.0441(14) -0.0060(12) -0.0015(12) 0.0032(14) C18 0.094(2) 0.080(2) 0.0403(14) 0.0081(13) 0.0109(13) -0.0076(17) C19 0.0766(17) 0.0752(18) 0.0464(15) 0.0089(13) 0.0127(12) -0.0153(15) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Cl1 C6 1.736(2) . ? Cl2 C17 1.744(3) . ? O1 C8 1.370(3) . ? O1 C1 1.445(3) . ? O2 C2 1.219(3) . ? N1 C2 1.365(3) . ? N1 C3 1.416(3) . ? N1 C13 1.466(3) . ? C1 C2 1.515(3) . ? C1 C9 1.548(3) . ? C1 H1 0.9800 . ? C3 C8 1.381(3) . ? C3 C4 1.387(3) . ? C4 C5 1.375(4) . ? C4 H4 0.9300 . ? C5 C6 1.379(4) . ? C5 H5 0.9300 . ? C6 C7 1.374(3) . ? C7 C8 1.383(3) . ? C7 H7 0.9300 . ? C9 C10 1.507(4) . ? C9 C12 1.511(4) . ? C9 C11 1.523(4) . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 C14 1.505(3) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 C15 1.381(3) . ? C14 C19 1.388(3) . ? C15 C16 1.376(3) . ? C15 H15 0.9300 . ? C16 C17 1.371(4) . ? C16 H16 0.9300 . ? C17 C18 1.363(4) . ? C18 C19 1.375(4) . ? C18 H18 0.9300 . ? C19 H19 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C8 O1 C1 116.32(16) . . ? C2 N1 C3 120.73(18) . . ? C2 N1 C13 118.61(19) . . ? C3 N1 C13 120.5(2) . . ? O1 C1 C2 112.06(19) . . ? O1 C1 C9 111.88(17) . . ? C2 C1 C9 115.18(19) . . ? O1 C1 H1 105.6 . . ? C2 C1 H1 105.6 . . ? C9 C1 H1 105.6 . . ? O2 C2 N1 122.0(2) . . ? O2 C2 C1 120.5(2) . . ? N1 C2 C1 117.54(19) . . ? C8 C3 C4 118.6(2) . . ? C8 C3 N1 118.76(19) . . ? C4 C3 N1 122.6(2) . . ? C5 C4 C3 120.6(2) . . ? C5 C4 H4 119.7 . . ? C3 C4 H4 119.7 . . ? C4 C5 C6 119.6(2) . . ? C4 C5 H5 120.2 . . ? C6 C5 H5 120.2 . . ? C7 C6 C5 120.9(2) . . ? C7 C6 Cl1 119.2(2) . . ? C5 C6 Cl1 119.8(2) . . ? C6 C7 C8 118.8(2) . . ? C6 C7 H7 120.6 . . ? C8 C7 H7 120.6 . . ? O1 C8 C3 120.37(19) . . ? O1 C8 C7 118.3(2) . . ? C3 C8 C7 121.3(2) . . ? C10 C9 C12 109.7(3) . . ? C10 C9 C11 108.2(3) . . ? C12 C9 C11 108.5(3) . . ? C10 C9 C1 112.5(2) . . ? C12 C9 C1 109.6(2) . . ? C11 C9 C1 108.2(2) . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C9 C11 H11A 109.5 . . ? C9 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C9 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C9 C12 H12A 109.5 . . ? C9 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C9 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? N1 C13 C14 115.8(2) . . ? N1 C13 H13A 108.3 . . ? C14 C13 H13A 108.3 . . ? N1 C13 H13B 108.3 . . ? C14 C13 H13B 108.3 . . ? H13A C13 H13B 107.4 . . ? C15 C14 C19 118.0(2) . . ? C15 C14 C13 123.9(2) . . ? C19 C14 C13 118.1(2) . . ? C16 C15 C14 121.1(2) . . ? C16 C15 H15 119.5 . . ? C14 C15 H15 119.5 . . ? C17 C16 C15 119.3(2) . . ? C17 C16 H16 120.3 . . ? C15 C16 H16 120.3 . . ? C18 C17 C16 121.1(2) . . ? C18 C17 Cl2 119.3(2) . . ? C16 C17 Cl2 119.6(2) . . ? C17 C18 C19 119.2(2) . . ? C17 C18 H18 120.4 . . ? C19 C18 H18 120.4 . . ? C18 C19 C14 121.3(2) . . ? C18 C19 H19 119.3 . . ? C14 C19 H19 119.3 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C8 O1 C1 C2 43.4(3) . . . . ? C8 O1 C1 C9 -87.8(2) . . . . ? C3 N1 C2 O2 178.2(2) . . . . ? C13 N1 C2 O2 -5.7(3) . . . . ? C3 N1 C2 C1 -2.6(3) . . . . ? C13 N1 C2 C1 173.5(2) . . . . ? O1 C1 C2 O2 152.6(2) . . . . ? C9 C1 C2 O2 -78.0(3) . . . . ? O1 C1 C2 N1 -26.6(3) . . . . ? C9 C1 C2 N1 102.8(2) . . . . ? C2 N1 C3 C8 17.1(3) . . . . ? C13 N1 C3 C8 -158.9(2) . . . . ? C2 N1 C3 C4 -162.7(2) . . . . ? C13 N1 C3 C4 21.2(3) . . . . ? C8 C3 C4 C5 1.3(4) . . . . ? N1 C3 C4 C5 -178.9(2) . . . . ? C3 C4 C5 C6 0.3(4) . . . . ? C4 C5 C6 C7 -1.5(4) . . . . ? C4 C5 C6 Cl1 179.3(2) . . . . ? C5 C6 C7 C8 0.9(4) . . . . ? Cl1 C6 C7 C8 -179.9(2) . . . . ? C1 O1 C8 C3 -31.4(3) . . . . ? C1 O1 C8 C7 150.5(2) . . . . ? C4 C3 C8 O1 -180.0(2) . . . . ? N1 C3 C8 O1 0.2(3) . . . . ? C4 C3 C8 C7 -1.9(4) . . . . ? N1 C3 C8 C7 178.3(2) . . . . ? C6 C7 C8 O1 178.9(2) . . . . ? C6 C7 C8 C3 0.8(4) . . . . ? O1 C1 C9 C10 66.8(3) . . . . ? C2 C1 C9 C10 -62.7(3) . . . . ? O1 C1 C9 C12 -170.9(2) . . . . ? C2 C1 C9 C12 59.6(3) . . . . ? O1 C1 C9 C11 -52.7(3) . . . . ? C2 C1 C9 C11 177.8(2) . . . . ? C2 N1 C13 C14 96.6(3) . . . . ? C3 N1 C13 C14 -87.2(3) . . . . ? N1 C13 C14 C15 7.9(4) . . . . ? N1 C13 C14 C19 -174.4(2) . . . . ? C19 C14 C15 C16 -1.0(4) . . . . ? C13 C14 C15 C16 176.7(2) . . . . ? C14 C15 C16 C17 0.4(4) . . . . ? C15 C16 C17 C18 0.2(4) . . . . ? C15 C16 C17 Cl2 -179.0(2) . . . . ? C16 C17 C18 C19 -0.1(4) . . . . ? Cl2 C17 C18 C19 179.0(2) . . . . ? C17 C18 C19 C14 -0.5(4) . . . . ? C15 C14 C19 C18 1.1(4) . . . . ? C13 C14 C19 C18 -176.8(3) . . . . ? _refine_diff_density_max 0.226 _refine_diff_density_min -0.219 _refine_diff_density_rms 0.038 _shelxl_version_number 2012-9 _shelx_res_file ; TITL CrystalBuilderInfo $monoclinic $P 21/c $? $colourless $ CELL 0.71073 5.954 8.628 34.703 90.000 93.476 90.000 ZERR 4 0.001 0.002 0.005 0.00 0.002 0.00 LATT 1 SYMM -X, 0.50000+Y, 0.50000-Z SFAC C H N O CL UNIT 76 76 4 8 8 CONF HTAB BOND $H DEFS 0.002 0.2 0.01 0.05 ! Global default restraint esds SIZE 0.1 0.1 0.1 TEMP 20 ACTA MERG 2 OMIT 0 0 6 OMIT 0 0 4 OMIT 0 0 2 OMIT 1 1 0 OMIT 0 1 2 OMIT -1 1 1 OMIT -1 0 4 OMIT 0 1 1 OMIT 0 1 3 L.S. 10 WPDB FMAP 2 PLAN 25 WGHT 0.050900 0.832000 EXTI 0.023905 FVAR 0.80979 CL1 5 -0.076344 0.258568 0.479747 11.00000 0.09369 0.09420 = 0.09675 -0.02078 0.02756 0.03387 CL2 5 -0.053875 -0.028148 0.192939 11.00000 0.12061 0.12292 = 0.05789 -0.01033 -0.02116 -0.01583 O1 4 0.587891 -0.060841 0.442730 11.00000 0.06585 0.06631 = 0.03993 -0.00514 -0.00552 0.02489 O2 4 0.808578 -0.150810 0.352848 11.00000 0.06232 0.08546 = 0.06244 -0.00255 0.02481 0.00914 N1 3 0.546145 0.027385 0.366324 11.00000 0.05409 0.05882 = 0.03855 0.00501 0.00560 0.00169 C1 1 0.659583 -0.171256 0.414692 11.00000 0.04335 0.05996 = 0.04304 -0.00462 0.00267 0.01406 AFIX 13 H1 2 0.813350 -0.200441 0.423459 11.00000 -1.20000 AFIX 0 C2 1 0.678109 -0.098505 0.375264 11.00000 0.04372 0.06021 = 0.04657 -0.00274 0.00282 0.00057 C3 1 0.391448 0.082857 0.392505 11.00000 0.05171 0.04403 = 0.04328 0.00168 -0.00107 0.00513 C4 1 0.215507 0.181646 0.381367 11.00000 0.07047 0.05254 = 0.05305 0.00390 -0.00760 0.00880 AFIX 43 H4 2 0.194725 0.212184 0.355698 11.00000 -1.20000 AFIX 0 C5 1 0.071577 0.234827 0.407920 11.00000 0.06466 0.05554 = 0.07864 -0.00251 -0.00701 0.02161 AFIX 43 H5 2 -0.046509 0.300613 0.400235 11.00000 -1.20000 AFIX 0 C6 1 0.103224 0.190110 0.446011 11.00000 0.06200 0.05379 = 0.06601 -0.01138 0.00813 0.01397 C7 1 0.273810 0.090235 0.457714 11.00000 0.07227 0.05573 = 0.04484 -0.00463 0.00567 0.01477 AFIX 43 H7 2 0.293181 0.059311 0.483372 11.00000 -1.20000 AFIX 0 C8 1 0.416158 0.036566 0.430614 11.00000 0.05393 0.04800 = 0.04230 -0.00187 -0.00135 0.01162 C9 1 0.520940 -0.322922 0.415048 11.00000 0.04806 0.05689 = 0.05019 0.00021 0.00920 0.00839 C10 1 0.278404 -0.299074 0.401344 11.00000 0.05906 0.07471 = 0.16675 0.01804 -0.02271 -0.00665 AFIX 137 H10A 2 0.270390 -0.266500 0.374845 11.00000 -1.50000 H10B 2 0.212846 -0.220979 0.416855 11.00000 -1.50000 H10C 2 0.197457 -0.394551 0.403601 11.00000 -1.50000 AFIX 0 C11 1 0.527467 -0.383175 0.456357 11.00000 0.14785 0.09275 = 0.06966 0.01936 0.01283 -0.00814 AFIX 137 H11A 2 0.448508 -0.480072 0.456966 11.00000 -1.50000 H11B 2 0.457002 -0.309331 0.472434 11.00000 -1.50000 H11C 2 0.681005 -0.398098 0.465708 11.00000 -1.50000 AFIX 0 C12 1 0.626367 -0.443062 0.390114 11.00000 0.10790 0.06553 = 0.12268 -0.02193 0.05022 0.00144 AFIX 137 H12A 2 0.554042 -0.541245 0.393357 11.00000 -1.50000 H12B 2 0.783685 -0.452157 0.397608 11.00000 -1.50000 H12C 2 0.608358 -0.412113 0.363534 11.00000 -1.50000 AFIX 0 C13 1 0.578000 0.109989 0.330147 11.00000 0.06661 0.06725 = 0.04736 0.00931 0.00707 -0.01009 AFIX 23 H13A 2 0.730947 0.092358 0.323020 11.00000 -1.20000 H13B 2 0.562041 0.220171 0.334817 11.00000 -1.20000 AFIX 0 C14 1 0.420018 0.065964 0.296426 11.00000 0.05695 0.05077 = 0.04165 0.00314 0.00872 0.00040 C15 1 0.236945 -0.030809 0.299194 11.00000 0.06659 0.06319 = 0.04217 0.00931 0.00686 -0.00881 AFIX 43 H15 2 0.211084 -0.076653 0.322771 11.00000 -1.20000 AFIX 0 C16 1 0.092194 -0.060507 0.267642 11.00000 0.06771 0.06633 = 0.05559 -0.00055 0.00655 -0.01016 AFIX 43 H16 2 -0.031058 -0.125396 0.269881 11.00000 -1.20000 AFIX 0 C17 1 0.131478 0.006518 0.232871 11.00000 0.07575 0.06232 = 0.04412 -0.00595 -0.00152 0.00321 C18 1 0.311632 0.101557 0.229029 11.00000 0.09431 0.08032 = 0.04034 0.00813 0.01092 -0.00756 AFIX 43 H18 2 0.336835 0.146247 0.205289 11.00000 -1.20000 AFIX 0 C19 1 0.455597 0.130515 0.260684 11.00000 0.07664 0.07522 = 0.04638 0.00895 0.01269 -0.01534 AFIX 43 H19 2 0.579310 0.194651 0.258093 11.00000 -1.20000 AFIX 0 HKLF 4 REM CrystalBuilderInfo $monoclinic $P 21/c $? $colourless $ REM R1 = 0.0512 for 2423 Fo > 4sig(Fo) and 0.0773 for all 3420 data REM 221 parameters refined using 0 restraints END WGHT 0.0506 0.8348 REM Instructions for potential hydrogen bonds EQIV $1 -x, y+1/2, -z+1/2 HTAB C4 Cl2_$1 EQIV $2 -x+1, -y, -z+1 HTAB C7 O1_$2 REM Highest difference peak 0.226, deepest hole -0.219, 1-sigma level 0.038 Q1 1 0.0417 0.3357 0.4791 11.00000 0.05 0.23 Q2 1 0.3654 -0.3178 0.3830 11.00000 0.05 0.20 Q3 1 -0.1883 -0.0721 0.2026 11.00000 0.05 0.18 Q4 1 0.3832 -0.3317 0.4484 11.00000 0.05 0.15 Q5 1 0.4256 -0.1206 0.4414 11.00000 0.05 0.15 Q6 1 0.2012 -0.2478 0.4416 11.00000 0.05 0.14 Q7 1 0.2949 0.0177 0.4380 11.00000 0.05 0.14 Q8 1 -0.0341 0.0382 0.2012 11.00000 0.05 0.14 Q9 1 0.7781 -0.4070 0.3723 11.00000 0.05 0.14 Q10 1 0.8945 -0.1165 0.3777 11.00000 0.05 0.14 Q11 1 0.3678 0.0261 0.4095 11.00000 0.05 0.14 Q12 1 0.2792 0.0542 0.3001 11.00000 0.05 0.13 Q13 1 0.4875 0.2630 0.3400 11.00000 0.05 0.13 Q14 1 0.0255 -0.0726 0.2686 11.00000 0.05 0.13 Q15 1 0.1214 -0.0531 0.2461 11.00000 0.05 0.13 Q16 1 0.5749 0.0621 0.3486 11.00000 0.05 0.13 Q17 1 0.2724 0.0990 0.3901 11.00000 0.05 0.12 Q18 1 0.0693 0.0042 0.2184 11.00000 0.05 0.12 Q19 1 0.5545 0.2820 0.2680 11.00000 0.05 0.12 Q20 1 0.2058 -0.2057 0.3835 11.00000 0.05 0.12 Q21 1 0.4225 -0.2685 0.4103 11.00000 0.05 0.12 Q22 1 0.4776 0.0016 0.4363 11.00000 0.05 0.12 Q23 1 0.4995 0.0789 0.3096 11.00000 0.05 0.12 Q24 1 0.5075 -0.0561 0.3662 11.00000 0.05 0.12 Q25 1 0.3167 -0.2936 0.3610 11.00000 0.05 0.12 ; _shelx_res_checksum 49877 _database_code_depnum_ccdc_archive 'CCDC 965236' ####################################################################### # # 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_compound_2r _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C20 H22 Br N O2' _chemical_formula_sum 'C20 H22 Br N O2' _chemical_formula_weight 388.30 _chemical_absolute_configuration ? loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -0.2901 2.4595 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_H-M_alt 'P 21/c' _space_group_name_Hall '-P 2ybc' _shelx_space_group_comment ; The symmetry employed for this shelxl refinement is uniquely defined by the following loop, which should always be used as a source of symmetry information in preference to the above space-group names. They are only intended as comments. ; loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y-1/2, z-1/2' _cell_length_a 7.2170(10) _cell_length_b 11.276(2) _cell_length_c 22.803(3) _cell_angle_alpha 90 _cell_angle_beta 92.725(3) _cell_angle_gamma 90 _cell_volume 1853.6(5) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 3241 _cell_measurement_theta_min 0.407 _cell_measurement_theta_max 25.350 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_max 0.51 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.24 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.391 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 800 _exptl_absorpt_coefficient_mu 2.229 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_correction_T_min 0.44 _exptl_absorpt_correction_T_max 0.58 _exptl_absorpt_process_details 'Scalepack (Otwinowski & Minor, 1997)' _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_source 'fine-focus sealed tube' _diffrn_source_type 'Nonius Kappa CCD' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Nonius kappa-CCD diffractometer' _diffrn_measurement_method 'phi and omega scans' _diffrn_detector_area_resol_mean 9 _diffrn_standards_number 0 _diffrn_standards_interval_count . _diffrn_standards_interval_time . _diffrn_standards_decay_% ? _diffrn_reflns_number 11449 _diffrn_reflns_av_unetI/netI 0.0620 _diffrn_reflns_av_R_equivalents 0.0350 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -27 _diffrn_reflns_limit_l_max 27 _diffrn_reflns_theta_min 3.354 _diffrn_reflns_theta_max 25.507 _diffrn_reflns_theta_full 25.240 _diffrn_measured_fraction_theta_max 0.981 _diffrn_measured_fraction_theta_full 0.987 _diffrn_reflns_Laue_measured_fraction_max 0.981 _diffrn_reflns_Laue_measured_fraction_full 0.987 _diffrn_reflns_point_group_measured_fraction_max 0.981 _diffrn_reflns_point_group_measured_fraction_full 0.987 _reflns_number_total 3395 _reflns_number_gt 2285 _reflns_threshold_expression 'I > 2\s(I)' _reflns_Friedel_coverage 0.000 _reflns_Friedel_fraction_max . _reflns_Friedel_fraction_full . _computing_data_collection 'DENZO (Otwinowski & Minor, 1997); COLLECT (Nonius B.V., 1999)' _computing_cell_refinement 'DENZO (Otwinowski & Minor, 1997); COLLECT (Nonius B.V., 1999)' _computing_data_reduction 'SCALEPACK (Otwinowski & Minor, 1997)' _computing_structure_solution 'SHELXS97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-2012 (Sheldrick, 2012);CRYSTALBUILDER (Welter, 2006)' _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material 'SHELXL97 (Sheldrick, 2008)' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; w=1/[\s^2^(Fo^2^)+(0.0598P)^2^+0.3912P] where P=(Fo^2^+2Fc^2^)/3 ; _atom_sites_solution_primary difmap _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method SHELXL _refine_ls_extinction_coef 0.014(2) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_number_reflns 3391 _refine_ls_number_parameters 221 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0770 _refine_ls_R_factor_gt 0.0473 _refine_ls_wR_factor_ref 0.1362 _refine_ls_wR_factor_gt 0.1178 _refine_ls_goodness_of_fit_ref 1.027 _refine_ls_restrained_S_all 1.027 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group Br1 Br 0.27603(6) 0.41810(4) 0.01430(2) 0.0865(3) Uani 1 1 d . . . . . O1 O 0.3572(3) 0.01587(19) 0.12105(9) 0.0547(6) Uani 1 1 d . . . . . O2 O 0.0963(3) -0.1423(2) 0.22359(10) 0.0684(7) Uani 1 1 d . . . . . N1 N 0.0573(3) 0.0453(2) 0.19063(11) 0.0463(6) Uani 1 1 d . . . . . C1 C 0.1348(4) -0.0642(3) 0.18885(14) 0.0495(8) Uani 1 1 d . . . . . C2 C 0.2671(4) -0.0900(3) 0.14086(14) 0.0500(8) Uani 1 1 d . . . . . H2 H 0.3654 -0.1398 0.1589 0.060 Uiso 1 1 calc R U . . . C3 C 0.2513(4) 0.1157(3) 0.11507(13) 0.0488(8) Uani 1 1 d . . . . . C4 C 0.1005(4) 0.1340(3) 0.14955(13) 0.0466(8) Uani 1 1 d . . . . . C5 C 0.0024(5) 0.2386(3) 0.14305(15) 0.0597(9) Uani 1 1 d . . . . . H5 H -0.0991 0.2520 0.1658 0.072 Uiso 1 1 calc R U . . . C6 C 0.0531(5) 0.3240(3) 0.10299(16) 0.0660(10) Uani 1 1 d . . . . . H6 H -0.0135 0.3943 0.0989 0.079 Uiso 1 1 calc R U . . . C7 C 0.2035(5) 0.3032(3) 0.06947(14) 0.0594(9) Uani 1 1 d . . . . . C8 C 0.3034(4) 0.2004(3) 0.07515(14) 0.0560(8) Uani 1 1 d . . . . . H8 H 0.4052 0.1876 0.0524 0.067 Uiso 1 1 calc R U . . . C9 C 0.1794(5) -0.1628(3) 0.08916(14) 0.0581(9) Uani 1 1 d . . . . . C10 C -0.0040(6) -0.1095(4) 0.06718(19) 0.0857(12) Uani 1 1 d . . . . . H10A H -0.0880 -0.1079 0.0986 0.129 Uiso 1 1 calc R U . . . H10B H -0.0561 -0.1568 0.0355 0.129 Uiso 1 1 calc R U . . . H10C H 0.0161 -0.0302 0.0536 0.129 Uiso 1 1 calc R U . . . C11 C 0.1484(6) -0.2897(3) 0.11031(18) 0.0784(11) Uani 1 1 d . . . . . H11A H 0.2648 -0.3235 0.1239 0.118 Uiso 1 1 calc R U . . . H11B H 0.0960 -0.3365 0.0785 0.118 Uiso 1 1 calc R U . . . H11C H 0.0649 -0.2889 0.1418 0.118 Uiso 1 1 calc R U . . . C12 C 0.3153(7) -0.1658(4) 0.0401(2) 0.1093(17) Uani 1 1 d . . . . . H12A H 0.3291 -0.0874 0.0246 0.164 Uiso 1 1 calc R U . . . H12B H 0.2690 -0.2179 0.0095 0.164 Uiso 1 1 calc R U . . . H12C H 0.4335 -0.1940 0.0554 0.164 Uiso 1 1 calc R U . . . C13 C -0.0808(4) 0.0667(3) 0.23478(14) 0.0511(8) Uani 1 1 d . . . . . H13A H -0.0804 0.1501 0.2452 0.061 Uiso 1 1 calc R U . . . H13B H -0.0478 0.0216 0.2699 0.061 Uiso 1 1 calc R U . . . C14 C -0.2741(4) 0.0311(3) 0.21175(16) 0.0626(9) Uani 1 1 d . . . . . H14A H -0.3098 0.0794 0.1779 0.075 Uiso 1 1 calc R U . . . H14B H -0.2728 -0.0511 0.1993 0.075 Uiso 1 1 calc R U . . . C15 C -0.4146(4) 0.0466(3) 0.25820(14) 0.0511(8) Uani 1 1 d . . . . . C16 C -0.4342(5) -0.0373(3) 0.30083(16) 0.0630(9) Uani 1 1 d . . . . . H16 H -0.3598 -0.1046 0.3011 0.076 Uiso 1 1 calc R U . . . C17 C -0.5619(5) -0.0241(4) 0.34325(17) 0.0744(11) Uani 1 1 d . . . . . H17 H -0.5734 -0.0823 0.3717 0.089 Uiso 1 1 calc R U . . . C18 C -0.6721(5) 0.0748(4) 0.34359(18) 0.0711(11) Uani 1 1 d . . . . . H18 H -0.7583 0.0844 0.3723 0.085 Uiso 1 1 calc R U . . . C19 C -0.6538(5) 0.1589(3) 0.30147(18) 0.0699(10) Uani 1 1 d . . . . . H19 H -0.7284 0.2261 0.3013 0.084 Uiso 1 1 calc R U . . . C20 C -0.5259(5) 0.1453(3) 0.25916(15) 0.0629(9) Uani 1 1 d . . . . . H20 H -0.5146 0.2038 0.2308 0.075 Uiso 1 1 calc R U . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Br1 0.1211(5) 0.0690(4) 0.0706(4) 0.01580(19) 0.0188(3) -0.0172(2) O1 0.0488(11) 0.0530(14) 0.0636(14) 0.0014(11) 0.0149(10) -0.0001(10) O2 0.0916(17) 0.0572(16) 0.0581(15) 0.0097(12) 0.0225(13) 0.0045(13) N1 0.0475(13) 0.0481(15) 0.0443(15) -0.0023(12) 0.0137(12) -0.0032(12) C1 0.0501(17) 0.053(2) 0.0451(19) -0.0010(15) 0.0032(15) -0.0031(15) C2 0.0502(17) 0.050(2) 0.0510(19) 0.0048(14) 0.0105(15) 0.0051(14) C3 0.0504(17) 0.0482(19) 0.0484(18) -0.0045(15) 0.0089(15) -0.0030(15) C4 0.0497(17) 0.0444(19) 0.0462(18) -0.0046(14) 0.0069(15) -0.0061(14) C5 0.063(2) 0.052(2) 0.065(2) -0.0034(17) 0.0168(18) 0.0006(16) C6 0.079(2) 0.053(2) 0.067(2) 0.0022(18) 0.010(2) 0.0043(18) C7 0.077(2) 0.054(2) 0.047(2) 0.0019(16) 0.0040(18) -0.0138(18) C8 0.0582(18) 0.062(2) 0.0492(19) -0.0044(16) 0.0160(16) -0.0110(17) C9 0.072(2) 0.053(2) 0.0497(19) -0.0053(16) 0.0123(17) 0.0032(16) C10 0.108(3) 0.077(3) 0.070(3) -0.012(2) -0.025(2) 0.005(2) C11 0.095(3) 0.056(2) 0.084(3) -0.005(2) 0.006(2) -0.001(2) C12 0.140(4) 0.112(4) 0.082(3) -0.029(3) 0.062(3) -0.023(3) C13 0.0536(17) 0.053(2) 0.0474(19) -0.0058(14) 0.0139(15) -0.0019(14) C14 0.0560(18) 0.071(2) 0.061(2) -0.0159(19) 0.0114(17) -0.0077(18) C15 0.0456(16) 0.054(2) 0.054(2) -0.0104(16) 0.0057(15) -0.0082(15) C16 0.0574(19) 0.056(2) 0.076(2) 0.000(2) 0.0095(19) 0.0012(17) C17 0.066(2) 0.082(3) 0.076(3) 0.017(2) 0.010(2) -0.009(2) C18 0.053(2) 0.101(3) 0.060(2) -0.006(2) 0.0142(18) 0.000(2) C19 0.062(2) 0.066(3) 0.083(3) -0.017(2) 0.009(2) 0.0112(18) C20 0.064(2) 0.060(2) 0.065(2) 0.0043(18) 0.0062(18) -0.0038(18) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_site_symmetry_2 _geom_bond_publ_flag Br1 C7 1.897(3) . ? O1 C3 1.364(4) . ? O1 C2 1.442(3) . ? O2 C1 1.225(4) . ? N1 C1 1.357(4) . ? N1 C4 1.415(4) . ? N1 C13 1.470(4) . ? C1 C2 1.514(4) . ? C2 C9 1.547(5) . ? C2 H2 0.9800 . ? C3 C8 1.383(4) . ? C3 C4 1.388(4) . ? C4 C5 1.380(4) . ? C5 C6 1.389(4) . ? C5 H5 0.9300 . ? C6 C7 1.377(5) . ? C6 H6 0.9300 . ? C7 C8 1.368(5) . ? C8 H8 0.9300 . ? C9 C10 1.516(5) . ? C9 C12 1.522(5) . ? C9 C11 1.531(5) . ? C10 H10A 0.9600 . ? C10 H10B 0.9600 . ? C10 H10C 0.9600 . ? C11 H11A 0.9600 . ? C11 H11B 0.9600 . ? C11 H11C 0.9600 . ? C12 H12A 0.9600 . ? C12 H12B 0.9600 . ? C12 H12C 0.9600 . ? C13 C14 1.521(4) . ? C13 H13A 0.9700 . ? C13 H13B 0.9700 . ? C14 C15 1.511(4) . ? C14 H14A 0.9700 . ? C14 H14B 0.9700 . ? C15 C16 1.369(5) . ? C15 C20 1.374(5) . ? C16 C17 1.375(5) . ? C16 H16 0.9300 . ? C17 C18 1.370(5) . ? C17 H17 0.9300 . ? C18 C19 1.360(5) . ? C18 H18 0.9300 . ? C19 C20 1.375(5) . ? C19 H19 0.9300 . ? C20 H20 0.9300 . ? loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_site_symmetry_1 _geom_angle_site_symmetry_3 _geom_angle_publ_flag C3 O1 C2 117.1(2) . . ? C1 N1 C4 121.3(2) . . ? C1 N1 C13 117.6(2) . . ? C4 N1 C13 121.0(2) . . ? O2 C1 N1 121.9(3) . . ? O2 C1 C2 119.9(3) . . ? N1 C1 C2 118.1(3) . . ? O1 C2 C1 112.1(2) . . ? O1 C2 C9 112.0(3) . . ? C1 C2 C9 113.8(2) . . ? O1 C2 H2 106.1 . . ? C1 C2 H2 106.1 . . ? C9 C2 H2 106.1 . . ? O1 C3 C8 117.8(3) . . ? O1 C3 C4 121.1(3) . . ? C8 C3 C4 121.0(3) . . ? C5 C4 C3 118.6(3) . . ? C5 C4 N1 123.1(3) . . ? C3 C4 N1 118.3(3) . . ? C4 C5 C6 120.9(3) . . ? C4 C5 H5 119.6 . . ? C6 C5 H5 119.6 . . ? C7 C6 C5 119.1(3) . . ? C7 C6 H6 120.4 . . ? C5 C6 H6 120.4 . . ? C8 C7 C6 121.2(3) . . ? C8 C7 Br1 118.7(3) . . ? C6 C7 Br1 120.1(3) . . ? C7 C8 C3 119.2(3) . . ? C7 C8 H8 120.4 . . ? C3 C8 H8 120.4 . . ? C10 C9 C12 110.4(4) . . ? C10 C9 C11 109.6(3) . . ? C12 C9 C11 108.6(3) . . ? C10 C9 C2 111.1(3) . . ? C12 C9 C2 108.5(3) . . ? C11 C9 C2 108.5(3) . . ? C9 C10 H10A 109.5 . . ? C9 C10 H10B 109.5 . . ? H10A C10 H10B 109.5 . . ? C9 C10 H10C 109.5 . . ? H10A C10 H10C 109.5 . . ? H10B C10 H10C 109.5 . . ? C9 C11 H11A 109.5 . . ? C9 C11 H11B 109.5 . . ? H11A C11 H11B 109.5 . . ? C9 C11 H11C 109.5 . . ? H11A C11 H11C 109.5 . . ? H11B C11 H11C 109.5 . . ? C9 C12 H12A 109.5 . . ? C9 C12 H12B 109.5 . . ? H12A C12 H12B 109.5 . . ? C9 C12 H12C 109.5 . . ? H12A C12 H12C 109.5 . . ? H12B C12 H12C 109.5 . . ? N1 C13 C14 111.2(3) . . ? N1 C13 H13A 109.4 . . ? C14 C13 H13A 109.4 . . ? N1 C13 H13B 109.4 . . ? C14 C13 H13B 109.4 . . ? H13A C13 H13B 108.0 . . ? C15 C14 C13 111.3(3) . . ? C15 C14 H14A 109.4 . . ? C13 C14 H14A 109.4 . . ? C15 C14 H14B 109.4 . . ? C13 C14 H14B 109.4 . . ? H14A C14 H14B 108.0 . . ? C16 C15 C20 117.9(3) . . ? C16 C15 C14 120.9(3) . . ? C20 C15 C14 121.1(3) . . ? C15 C16 C17 121.3(3) . . ? C15 C16 H16 119.3 . . ? C17 C16 H16 119.3 . . ? C18 C17 C16 120.0(4) . . ? C18 C17 H17 120.0 . . ? C16 C17 H17 120.0 . . ? C19 C18 C17 119.2(3) . . ? C19 C18 H18 120.4 . . ? C17 C18 H18 120.4 . . ? C18 C19 C20 120.6(3) . . ? C18 C19 H19 119.7 . . ? C20 C19 H19 119.7 . . ? C15 C20 C19 120.9(3) . . ? C15 C20 H20 119.5 . . ? C19 C20 H20 119.5 . . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag C4 N1 C1 O2 -178.8(3) . . . . ? C13 N1 C1 O2 -2.0(5) . . . . ? C4 N1 C1 C2 -1.0(4) . . . . ? C13 N1 C1 C2 175.8(3) . . . . ? C3 O1 C2 C1 -40.5(4) . . . . ? C3 O1 C2 C9 88.9(3) . . . . ? O2 C1 C2 O1 -155.2(3) . . . . ? N1 C1 C2 O1 26.9(4) . . . . ? O2 C1 C2 C9 76.3(4) . . . . ? N1 C1 C2 C9 -101.5(3) . . . . ? C2 O1 C3 C8 -153.6(3) . . . . ? C2 O1 C3 C4 28.9(4) . . . . ? O1 C3 C4 C5 177.7(3) . . . . ? C8 C3 C4 C5 0.3(5) . . . . ? O1 C3 C4 N1 -1.0(4) . . . . ? C8 C3 C4 N1 -178.4(3) . . . . ? C1 N1 C4 C5 168.3(3) . . . . ? C13 N1 C4 C5 -8.4(4) . . . . ? C1 N1 C4 C3 -13.1(4) . . . . ? C13 N1 C4 C3 170.2(3) . . . . ? C3 C4 C5 C6 -0.1(5) . . . . ? N1 C4 C5 C6 178.5(3) . . . . ? C4 C5 C6 C7 0.1(5) . . . . ? C5 C6 C7 C8 -0.2(5) . . . . ? C5 C6 C7 Br1 179.9(3) . . . . ? C6 C7 C8 C3 0.4(5) . . . . ? Br1 C7 C8 C3 -179.7(2) . . . . ? O1 C3 C8 C7 -177.9(3) . . . . ? C4 C3 C8 C7 -0.5(5) . . . . ? O1 C2 C9 C10 -78.9(3) . . . . ? C1 C2 C9 C10 49.6(4) . . . . ? O1 C2 C9 C12 42.7(4) . . . . ? C1 C2 C9 C12 171.2(3) . . . . ? O1 C2 C9 C11 160.5(3) . . . . ? C1 C2 C9 C11 -71.0(3) . . . . ? C1 N1 C13 C14 -86.9(3) . . . . ? C4 N1 C13 C14 90.0(3) . . . . ? N1 C13 C14 C15 176.8(3) . . . . ? C13 C14 C15 C16 -81.0(4) . . . . ? C13 C14 C15 C20 98.7(4) . . . . ? C20 C15 C16 C17 0.3(5) . . . . ? C14 C15 C16 C17 -179.9(3) . . . . ? C15 C16 C17 C18 -0.3(6) . . . . ? C16 C17 C18 C19 0.2(6) . . . . ? C17 C18 C19 C20 -0.3(6) . . . . ? C16 C15 C20 C19 -0.4(5) . . . . ? C14 C15 C20 C19 179.9(3) . . . . ? C18 C19 C20 C15 0.4(5) . . . . ? _refine_diff_density_max 0.448 _refine_diff_density_min -0.452 _refine_diff_density_rms 0.053 _shelxl_version_number 2012-9 _shelx_res_file ; TITL CrystalBuilderInfo $monoclinic $P 21/c $? $colourless $ CELL 0.71069 7.217 11.276 22.803 90.000 92.725 90.000 ZERR 4 0.001 0.002 0.003 0.000 0.003 0.000 LATT 1 SYMM -X, 0.50000+Y, 0.50000-Z SFAC C H N O BR UNIT 80 88 4 8 4 CONF BOND $H DEFS 0.002 0.2 0.01 0.05 ! Global default restraint esds SIZE 0.1 0.1 0.1 TEMP 20 MERG 2 ACTA OMIT 0 1 1 OMIT 1 0 0 OMIT 0 0 2 OMIT -1 3 22 L.S. 10 WPDB FMAP 2 PLAN 25 WGHT 0.059800 0.391200 EXTI 0.013546 FVAR 0.57915 BR1 5 0.276026 0.418105 0.014295 11.00000 0.12112 0.06905 = 0.07057 0.01580 0.01875 -0.01716 O1 4 0.357230 0.015871 0.121053 11.00000 0.04875 0.05301 = 0.06363 0.00142 0.01489 -0.00015 O2 4 0.096317 -0.142290 0.223591 11.00000 0.09157 0.05715 = 0.05814 0.00974 0.02248 0.00447 N1 3 0.057289 0.045330 0.190630 11.00000 0.04748 0.04809 = 0.04435 -0.00230 0.01371 -0.00323 C1 1 0.134787 -0.064178 0.188852 11.00000 0.05015 0.05337 = 0.04506 -0.00095 0.00319 -0.00314 C2 1 0.267051 -0.089978 0.140863 11.00000 0.05018 0.04955 = 0.05102 0.00478 0.01048 0.00514 AFIX 13 H2 2 0.365436 -0.139805 0.158851 11.00000 -1.20000 AFIX 0 C3 1 0.251253 0.115700 0.115067 11.00000 0.05035 0.04815 = 0.04842 -0.00447 0.00890 -0.00303 C4 1 0.100531 0.133993 0.149548 11.00000 0.04966 0.04440 = 0.04622 -0.00461 0.00695 -0.00610 C5 1 0.002372 0.238569 0.143045 11.00000 0.06324 0.05195 = 0.06532 -0.00344 0.01678 0.00058 AFIX 43 H5 2 -0.099136 0.252016 0.165794 11.00000 -1.20000 AFIX 0 C6 1 0.053145 0.323985 0.102988 11.00000 0.07859 0.05274 = 0.06725 0.00216 0.01038 0.00434 AFIX 43 H6 2 -0.013507 0.394317 0.098857 11.00000 -1.20000 AFIX 0 C7 1 0.203479 0.303156 0.069471 11.00000 0.07734 0.05371 = 0.04737 0.00195 0.00399 -0.01383 C8 1 0.303370 0.200372 0.075154 11.00000 0.05825 0.06172 = 0.04920 -0.00437 0.01597 -0.01098 AFIX 43 H8 2 0.405164 0.187552 0.052446 11.00000 -1.20000 AFIX 0 C9 1 0.179384 -0.162761 0.089159 11.00000 0.07222 0.05324 = 0.04973 -0.00530 0.01234 0.00322 C10 1 -0.003972 -0.109519 0.067180 11.00000 0.10758 0.07712 = 0.06979 -0.01216 -0.02468 0.00506 AFIX 137 H10A 2 -0.087983 -0.107878 0.098570 11.00000 -1.50000 H10B 2 -0.056060 -0.156779 0.035492 11.00000 -1.50000 H10C 2 0.016054 -0.030196 0.053563 11.00000 -1.50000 AFIX 0 C11 1 0.148372 -0.289741 0.110307 11.00000 0.09528 0.05591 = 0.08418 -0.00488 0.00585 -0.00141 AFIX 137 H11A 2 0.264790 -0.323476 0.123872 11.00000 -1.50000 H11B 2 0.095995 -0.336468 0.078465 11.00000 -1.50000 H11C 2 0.064881 -0.288915 0.141846 11.00000 -1.50000 AFIX 0 C12 1 0.315302 -0.165773 0.040142 11.00000 0.13974 0.11163 = 0.08189 -0.02890 0.06169 -0.02262 AFIX 137 H12A 2 0.329144 -0.087353 0.024555 11.00000 -1.50000 H12B 2 0.269015 -0.217877 0.009538 11.00000 -1.50000 H12C 2 0.433469 -0.193990 0.055417 11.00000 -1.50000 AFIX 0 C13 1 -0.080808 0.066728 0.234781 11.00000 0.05360 0.05344 = 0.04743 -0.00583 0.01392 -0.00191 AFIX 23 H13A 2 -0.080407 0.150149 0.245171 11.00000 -1.20000 H13B 2 -0.047791 0.021580 0.269950 11.00000 -1.20000 AFIX 0 C14 1 -0.274098 0.031143 0.211754 11.00000 0.05599 0.07119 = 0.06131 -0.01593 0.01144 -0.00771 AFIX 23 H14A 2 -0.309847 0.079420 0.177871 11.00000 -1.20000 H14B 2 -0.272789 -0.051089 0.199291 11.00000 -1.20000 AFIX 0 C15 1 -0.414567 0.046585 0.258199 11.00000 0.04562 0.05399 = 0.05411 -0.01038 0.00567 -0.00817 C16 1 -0.434227 -0.037324 0.300831 11.00000 0.05739 0.05594 = 0.07624 0.00008 0.00948 0.00120 AFIX 43 H16 2 -0.359753 -0.104648 0.301115 11.00000 -1.20000 AFIX 0 C17 1 -0.561852 -0.024104 0.343248 11.00000 0.06606 0.08212 = 0.07565 0.01706 0.01026 -0.00909 AFIX 43 H17 2 -0.573379 -0.082341 0.371723 11.00000 -1.20000 AFIX 0 C18 1 -0.672069 0.074836 0.343588 11.00000 0.05319 0.10140 = 0.05994 -0.00648 0.01420 -0.00031 AFIX 43 H18 2 -0.758291 0.084396 0.372257 11.00000 -1.20000 AFIX 0 C19 1 -0.653778 0.158866 0.301475 11.00000 0.06164 0.06602 = 0.08260 -0.01721 0.00923 0.01124 AFIX 43 H19 2 -0.728424 0.226107 0.301292 11.00000 -1.20000 AFIX 0 C20 1 -0.525899 0.145296 0.259162 11.00000 0.06393 0.05978 = 0.06529 0.00434 0.00618 -0.00380 AFIX 43 H20 2 -0.514632 0.203779 0.230795 11.00000 -1.20000 AFIX 0 HKLF 4 REM CrystalBuilderInfo $monoclinic $P 21/c $? $colourless $ REM R1 = 0.0473 for 2285 Fo > 4sig(Fo) and 0.0770 for all 3391 data REM 221 parameters refined using 0 restraints END WGHT 0.0598 0.3909 REM Highest difference peak 0.448, deepest hole -0.452, 1-sigma level 0.053 Q1 1 0.3300 0.3564 -0.0046 11.00000 0.05 0.27 Q2 1 0.2312 -0.1558 0.0645 11.00000 0.05 0.25 Q3 1 0.2611 -0.2598 0.0111 11.00000 0.05 0.24 Q4 1 0.2182 -0.0760 0.1675 11.00000 0.05 0.22 Q5 1 0.3432 0.1981 0.0671 11.00000 0.05 0.21 Q6 1 0.1608 0.4216 -0.0460 11.00000 0.05 0.21 Q7 1 0.1690 0.3041 0.0821 11.00000 0.05 0.20 Q8 1 -0.0615 -0.0362 0.0730 11.00000 0.05 0.19 Q9 1 -0.4789 0.1640 0.1992 11.00000 0.05 0.19 Q10 1 0.3245 0.5031 0.0629 11.00000 0.05 0.19 Q11 1 0.2376 -0.3909 -0.0195 11.00000 0.05 0.19 Q12 1 0.1381 -0.0411 0.2862 11.00000 0.05 0.18 Q13 1 0.3085 -0.3956 0.0535 11.00000 0.05 0.17 Q14 1 -0.5085 0.1665 0.2497 11.00000 0.05 0.16 Q15 1 0.0445 0.0792 0.1786 11.00000 0.05 0.16 Q16 1 -0.1333 -0.1744 0.0977 11.00000 0.05 0.16 Q17 1 0.3470 0.2968 -0.0399 11.00000 0.05 0.16 Q18 1 -0.4741 -0.0961 0.3827 11.00000 0.05 0.16 Q19 1 -0.0481 -0.1332 0.0699 11.00000 0.05 0.16 Q20 1 0.1559 0.4964 0.0529 11.00000 0.05 0.15 Q21 1 0.4015 -0.3071 0.0395 11.00000 0.05 0.15 Q22 1 -0.0644 0.5374 0.0667 11.00000 0.05 0.15 Q23 1 0.2241 0.5049 -0.0318 11.00000 0.05 0.15 Q24 1 0.0893 0.0365 0.3251 11.00000 0.05 0.15 Q25 1 -0.3162 0.1396 0.1780 11.00000 0.05 0.15 ; _shelx_res_checksum 4013 #==END _database_code_depnum_ccdc_archive 'CCDC 965237'