# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is © The Royal Society of Chemistry 2012 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # ####################################################################### data_p212121 _database_code_depnum_ccdc_archive 'CCDC 878581' #TrackingRef 'OrtizAdrianCCDC.cif' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C20 H30 Cl2 N2 O2' _chemical_formula_weight 401.36 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M 'P2(1)2(1)2(1) ' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' _cell_length_a 5.7182(3) _cell_length_b 12.0175(7) _cell_length_c 30.1828(17) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 2074.1(2) _cell_formula_units_Z 4 _cell_measurement_temperature 203(2) _cell_measurement_reflns_used 6947 _cell_measurement_theta_min 4.70 _cell_measurement_theta_max 54.98 _exptl_crystal_description blade _exptl_crystal_colour colourless _exptl_crystal_size_max 0.30 _exptl_crystal_size_mid 0.08 _exptl_crystal_size_min 0.03 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.285 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 856 _exptl_absorpt_coefficient_mu 2.941 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? _exptl_special_details ; ? ; _diffrn_ambient_temperature 203(2) _diffrn_radiation_wavelength 1.54178 _diffrn_radiation_type CuK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_detector_area_resol_mean ? _diffrn_reflns_number 12961 _diffrn_reflns_av_R_equivalents 0.0497 _diffrn_reflns_av_sigmaI/netI 0.0415 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 5 _diffrn_reflns_limit_k_min -12 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -32 _diffrn_reflns_limit_l_max 31 _diffrn_reflns_theta_min 2.93 _diffrn_reflns_theta_max 55.23 _reflns_number_total 2579 _reflns_number_gt 2418 _reflns_threshold_expression >2sigma(I) _computing_data_collection 'Bruker APEX2' _computing_cell_refinement 'Bruker SAINT' _computing_data_reduction 'Bruker SAINT' _computing_structure_solution 'SHELXS-97 (Sheldrick, 2008)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 2008)' _computing_molecular_graphics 'Bruker SHELXTL' _computing_publication_material 'Bruker SHELXTL' _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0531P)^2^+0.5707P] 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 none _refine_ls_extinction_coef ? _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack 0.044(19) _refine_ls_number_reflns 2579 _refine_ls_number_parameters 241 _refine_ls_number_restraints 1 _refine_ls_R_factor_all 0.0402 _refine_ls_R_factor_gt 0.0372 _refine_ls_wR_factor_ref 0.0979 _refine_ls_wR_factor_gt 0.0966 _refine_ls_goodness_of_fit_ref 1.101 _refine_ls_restrained_S_all 1.100 _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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags _atom_site_disorder_assembly _atom_site_disorder_group C1 C 0.5508(6) 0.6021(3) 0.10380(10) 0.0326(8) Uani 1 1 d . . . C2 C 0.3445(6) 0.5563(3) 0.08759(11) 0.0370(8) Uani 1 1 d . . . H2 H 0.2369 0.5247 0.1075 0.044 Uiso 1 1 calc R . . C3 C 0.2949(7) 0.5564(3) 0.04294(12) 0.0422(9) Uani 1 1 d . . . H3 H 0.1554 0.5240 0.0327 0.051 Uiso 1 1 calc R . . C4 C 0.4483(7) 0.6035(3) 0.01325(12) 0.0453(9) Uani 1 1 d . . . H4 H 0.4137 0.6040 -0.0172 0.054 Uiso 1 1 calc R . . C5 C 0.6535(7) 0.6502(3) 0.02866(12) 0.0463(10) Uani 1 1 d . . . H5 H 0.7596 0.6822 0.0086 0.056 Uiso 1 1 calc R . . C6 C 0.7042(6) 0.6503(3) 0.07376(11) 0.0406(9) Uani 1 1 d . . . H6 H 0.8434 0.6831 0.0840 0.049 Uiso 1 1 calc R . . C7 C 0.6193(6) 0.5995(3) 0.15169(10) 0.0359(8) Uani 1 1 d . . . H7A H 0.6806 0.5254 0.1588 0.043 Uiso 1 1 calc R . . H7B H 0.7453 0.6534 0.1566 0.043 Uiso 1 1 calc R . . C8 C 0.5006(5) 0.6549(3) 0.22825(10) 0.0265(7) Uani 1 1 d . . . H8 H 0.6047 0.7206 0.2265 0.032 Uiso 1 1 calc R . . C9 C 0.2909(6) 0.6840(3) 0.25681(10) 0.0287(7) Uani 1 1 d . . . H9 H 0.1869 0.6184 0.2591 0.034 Uiso 1 1 calc R . . C10 C 0.3717(6) 0.7174(3) 0.30285(10) 0.0295(7) Uani 1 1 d . . . H10A H 0.4709 0.7837 0.3009 0.035 Uiso 1 1 calc R . . H10B H 0.2356 0.7358 0.3212 0.035 Uiso 1 1 calc R . . C11 C 0.7099(5) 0.5910(3) 0.29602(10) 0.0325(7) Uani 1 1 d . . . H11A H 0.7890 0.5276 0.3099 0.039 Uiso 1 1 calc R . . H11B H 0.8217 0.6527 0.2944 0.039 Uiso 1 1 calc R . . C12 C 0.6342(6) 0.5595(3) 0.24987(10) 0.0301(7) Uani 1 1 d . . . H12A H 0.5341 0.4933 0.2512 0.036 Uiso 1 1 calc R . . H12B H 0.7720 0.5413 0.2320 0.036 Uiso 1 1 calc R . . C13 C 0.5925(6) 0.6523(3) 0.36985(11) 0.0394(8) Uani 1 1 d . . . H13A H 0.7112 0.7109 0.3677 0.047 Uiso 1 1 calc R . . H13B H 0.6674 0.5862 0.3825 0.047 Uiso 1 1 calc R . . C14 C 0.3996(6) 0.6908(3) 0.40076(11) 0.0379(8) Uani 1 1 d . . . C15 C 0.3781(8) 0.8023(3) 0.41089(13) 0.0526(10) Uani 1 1 d . . . H15 H 0.4836 0.8536 0.3985 0.063 Uiso 1 1 calc R . . C16 C 0.2052(8) 0.8394(3) 0.43874(14) 0.0637(12) Uani 1 1 d . . . H16 H 0.1930 0.9156 0.4453 0.076 Uiso 1 1 calc R . . C17 C 0.0492(8) 0.7651(3) 0.45717(13) 0.0559(11) Uani 1 1 d . . . H17 H -0.0709 0.7906 0.4759 0.067 Uiso 1 1 calc R . . C18 C 0.0706(7) 0.6538(3) 0.44802(12) 0.0511(10) Uani 1 1 d . . . H18 H -0.0334 0.6028 0.4610 0.061 Uiso 1 1 calc R . . C19 C 0.2438(7) 0.6158(3) 0.41985(12) 0.0482(10) Uani 1 1 d . . . H19 H 0.2564 0.5394 0.4136 0.058 Uiso 1 1 calc R . . Cl1 Cl 0.11878(13) 0.40559(7) 0.18849(3) 0.0365(2) Uani 1 1 d . . . Cl2 Cl 0.24090(16) 0.40943(8) 0.32913(3) 0.0534(3) Uani 1 1 d . . . N1 N 0.4220(4) 0.62537(19) 0.18251(8) 0.0271(6) Uani 1 1 d . . . H1A H 0.3256 0.5653 0.1840 0.032 Uiso 1 1 calc R . . H1B H 0.3381 0.6831 0.1712 0.032 Uiso 1 1 calc R . . N2 N 0.5056(4) 0.6250(2) 0.32397(8) 0.0289(6) Uani 1 1 d D . . H2N H 0.407(5) 0.5623(17) 0.3282(10) 0.035 Uiso 1 1 d D . . O1 O 0.1691(4) 0.7720(2) 0.23607(7) 0.0481(7) Uani 1 1 d . . . H1 H 0.0808 0.8021 0.2543 0.072 Uiso 1 1 calc R . . O1S O 0.1691(5) 0.7807(2) 0.13587(8) 0.0622(8) Uani 1 1 d . . . H1S H 0.0774 0.8174 0.1514 0.093 Uiso 1 1 calc R . . C1S C 0.2362(8) 0.8430(4) 0.09969(14) 0.0642(12) Uani 1 1 d . . . H1S1 H 0.1170 0.8981 0.0933 0.096 Uiso 1 1 calc R . . H1S2 H 0.2558 0.7946 0.0742 0.096 Uiso 1 1 calc R . . H1S3 H 0.3830 0.8801 0.1061 0.096 Uiso 1 1 calc R . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 C1 0.0345(19) 0.0218(17) 0.0415(19) -0.0001(14) 0.0107(14) 0.0050(16) C2 0.040(2) 0.0291(19) 0.042(2) 0.0012(14) 0.0105(16) -0.0013(16) C3 0.045(2) 0.0329(19) 0.049(2) -0.0047(16) 0.0016(18) -0.0003(17) C4 0.058(2) 0.038(2) 0.0406(19) -0.0017(17) 0.0024(17) 0.005(2) C5 0.054(2) 0.040(2) 0.045(2) 0.0039(16) 0.0174(18) -0.005(2) C6 0.037(2) 0.039(2) 0.046(2) -0.0022(15) 0.0077(16) -0.0031(18) C7 0.0290(17) 0.039(2) 0.0401(19) 0.0003(15) 0.0093(15) 0.0071(18) C8 0.0195(15) 0.0233(17) 0.0368(17) 0.0001(13) 0.0031(13) 0.0003(15) C9 0.0234(17) 0.0285(18) 0.0340(17) -0.0011(13) 0.0035(13) 0.0055(15) C10 0.0247(17) 0.0244(17) 0.0392(18) -0.0009(13) 0.0036(14) 0.0070(15) C11 0.0194(16) 0.0329(18) 0.0452(19) 0.0058(14) 0.0056(13) 0.0082(16) C12 0.0243(17) 0.0264(18) 0.0397(18) 0.0007(13) 0.0056(14) 0.0046(15) C13 0.0365(19) 0.038(2) 0.044(2) 0.0025(15) -0.0086(16) -0.0005(18) C14 0.0375(19) 0.037(2) 0.0390(19) 0.0015(15) -0.0033(16) -0.0042(18) C15 0.070(3) 0.027(2) 0.061(2) -0.0071(17) 0.013(2) -0.007(2) C16 0.085(3) 0.036(2) 0.070(3) -0.0072(19) 0.022(3) 0.001(2) C17 0.065(3) 0.055(3) 0.047(2) -0.001(2) 0.008(2) 0.014(2) C18 0.055(3) 0.049(3) 0.050(2) 0.0102(18) 0.0034(19) -0.008(2) C19 0.062(3) 0.028(2) 0.055(2) 0.0007(16) 0.005(2) 0.005(2) Cl1 0.0306(4) 0.0289(4) 0.0499(5) 0.0026(4) 0.0081(4) -0.0026(4) Cl2 0.0510(6) 0.0364(5) 0.0726(6) -0.0054(4) 0.0117(4) -0.0172(5) N1 0.0241(13) 0.0210(14) 0.0361(14) 0.0017(11) 0.0044(11) 0.0045(11) N2 0.0281(14) 0.0246(15) 0.0341(15) 0.0010(11) 0.0017(11) 0.0010(12) O1 0.0512(18) 0.0528(16) 0.0401(14) 0.0019(11) 0.0019(11) 0.0358(14) O1S 0.073(2) 0.0668(18) 0.0467(16) 0.0070(13) 0.0049(14) 0.0374(17) C1S 0.066(3) 0.056(3) 0.071(3) 0.002(2) 0.000(2) 0.013(3) _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 C1 C6 1.388(5) . ? C1 C2 1.391(5) . ? C1 C7 1.498(5) . ? C2 C3 1.377(5) . ? C3 C4 1.376(5) . ? C4 C5 1.381(5) . ? C5 C6 1.392(5) . ? C7 N1 1.495(4) . ? C8 N1 1.495(4) . ? C8 C9 1.517(4) . ? C8 C12 1.524(4) . ? C9 O1 1.412(4) . ? C9 C10 1.518(4) . ? C10 N2 1.492(4) . ? C11 N2 1.498(4) . ? C11 C12 1.507(5) . ? C13 N2 1.508(4) . ? C13 C14 1.517(5) . ? C14 C15 1.380(5) . ? C14 C19 1.392(5) . ? C15 C16 1.372(6) . ? C16 C17 1.379(6) . ? C17 C18 1.372(6) . ? C18 C19 1.383(5) . ? O1S C1S 1.379(5) . ? 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 C6 C1 C2 118.1(3) . . ? C6 C1 C7 118.3(3) . . ? C2 C1 C7 123.6(3) . . ? C3 C2 C1 121.3(3) . . ? C4 C3 C2 120.4(3) . . ? C3 C4 C5 119.3(3) . . ? C4 C5 C6 120.4(3) . . ? C1 C6 C5 120.5(3) . . ? N1 C7 C1 113.5(3) . . ? N1 C8 C9 110.0(2) . . ? N1 C8 C12 111.6(2) . . ? C9 C8 C12 109.0(3) . . ? O1 C9 C8 108.1(2) . . ? O1 C9 C10 111.0(3) . . ? C8 C9 C10 109.9(3) . . ? N2 C10 C9 110.5(2) . . ? N2 C11 C12 111.4(2) . . ? C11 C12 C8 110.5(3) . . ? N2 C13 C14 113.1(3) . . ? C15 C14 C19 118.7(3) . . ? C15 C14 C13 119.8(3) . . ? C19 C14 C13 121.5(3) . . ? C16 C15 C14 121.0(4) . . ? C15 C16 C17 120.2(4) . . ? C18 C17 C16 119.5(4) . . ? C17 C18 C19 120.7(4) . . ? C18 C19 C14 119.9(3) . . ? C7 N1 C8 113.4(2) . . ? C10 N2 C11 111.2(2) . . ? C10 N2 C13 113.5(2) . . ? C11 N2 C13 108.6(2) . . ? _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 55.23 _diffrn_measured_fraction_theta_full 0.987 _refine_diff_density_max 0.236 _refine_diff_density_min -0.228 _refine_diff_density_rms 0.047