#------------------------------------------------------------------------------ #$Date: 2013-12-28 09:07:06 +0200 (Sat, 28 Dec 2013) $ #$Revision: 91932 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/50/42/1504240.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/ # # All data on this site have been placed in the public domain by the # contributors. # data_1504240 loop_ _publ_author_name 'Maugel, Nathan' 'Snider, Barry B.' _publ_section_title ; Efficient synthesis of the tetracyclic aminoquinone moiety of marmycin A. ; _journal_issue 21 _journal_name_full 'Organic letters' _journal_page_first 4926 _journal_page_last 4929 _journal_volume 11 _journal_year 2009 _chemical_formula_moiety 'C38.76 H26.76 Cl2.28 N2 O4' _chemical_formula_sum 'C38.76 H26.76 Cl2.28 N2 O4' _chemical_formula_weight 665.16 _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2yn' _symmetry_space_group_name_H-M 'P 1 21/n 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _cell_angle_alpha 90 _cell_angle_beta 90.060(5) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 14.1491(11) _cell_length_b 15.4750(12) _cell_length_c 14.3939(11) _cell_measurement_reflns_used 5610 _cell_measurement_temperature 120 _cell_measurement_theta_max 26 _cell_measurement_theta_min 3 _cell_volume 3151.6(4) _computing_cell_refinement 'Apex2 (Bruker AXS, 2006)' _computing_data_collection 'Apex2 (Bruker AXS, 2006)' _computing_data_reduction 'Apex2 (Bruker AXS, 2006)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _diffrn_ambient_temperature 120 _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 0.992 _diffrn_measurement_device 'Bruker Kappa Apex2' _diffrn_measurement_device_type Area _diffrn_measurement_method '\f & \w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.056 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_l_max 18 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_number 32698 _diffrn_reflns_theta_full 26.690 _diffrn_reflns_theta_max 27.234 _diffrn_reflns_theta_min 1.932 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.276 _exptl_absorpt_correction_T_max 0.98 _exptl_absorpt_correction_T_min 0.97 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'Apex2 (Bruker AXS, 2006)' _exptl_crystal_colour red _exptl_crystal_density_diffrn 1.402 _exptl_crystal_density_method 'not measured' _exptl_crystal_description 'acicular fragment' _exptl_crystal_F_000 1375.937 _exptl_crystal_size_max 0.692 _exptl_crystal_size_mid 0.110 _exptl_crystal_size_min 0.084 _refine_diff_density_max 0.78 _refine_diff_density_min -0.46 _refine_ls_extinction_method None _refine_ls_goodness_of_fit_ref 0.9575 _refine_ls_hydrogen_treatment none _refine_ls_matrix_type full _refine_ls_number_parameters 444 _refine_ls_number_reflns 6986 _refine_ls_number_restraints 2 _refine_ls_R_factor_all 0.0947 _refine_ls_R_factor_gt 0.0781 _refine_ls_shift/su_max 0.0192733 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 10.7 16.3 7.32 1.63 ; _refine_ls_weighting_scheme calc _refine_ls_wR_factor_all 0.1993 _refine_ls_wR_factor_gt 0.1790 _refine_ls_wR_factor_ref 0.1993 _reflns_limit_h_max 18 _reflns_limit_h_min -18 _reflns_limit_k_max 19 _reflns_limit_k_min 0 _reflns_limit_l_max 18 _reflns_limit_l_min 0 _reflns_number_gt 5808 _reflns_number_total 6986 _reflns_threshold_expression I>2.0\s(I) _oxford_diffrn_Wilson_B_factor 2.17 _oxford_diffrn_Wilson_scale 94.85 _oxford_refine_ls_r_factor_ref 0.0947 _oxford_refine_ls_scale 0.06508(3) _oxford_reflns_number_all 6986 _oxford_reflns_threshold_expression_ref I>-10.0\s(I) _[local]_cod_data_source_file ol9020496_si_002.cif _[local]_cod_data_source_block NM7_48_3 _[local]_cod_cif_authors_sg_H-M 'P 1 21/n 1 ' _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26. '_exptl_absorpt_correction_type' value 'Multi-scan' changed to 'multi-scan' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana ; _cod_database_code 1504240 loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z -x+1/2,y+1/2,-z+1/2 x+1/2,-y+1/2,z+1/2 loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl 0.45035(14) 0.49835(14) 0.12946(12) 0.0593 0.758(5) Uani . P . . Cl3 Cl 0.40431(12) 0.55734(10) 0.31117(12) 0.0479 0.758(5) Uani . P . . Cl20 Cl 0.5892(4) 0.4902(6) 0.2759(3) 0.0822 0.379(2) Uani D P 1 1 Cl21 Cl 0.5781(6) 0.4700(8) 0.2884(12) 0.2157 0.379(2) Uani D P 1 2 O1 O 0.5258(2) 1.25106(17) 0.4193(2) 0.0318 1.0000 Uani . . . . O2 O 0.6632(2) 0.92836(17) 0.4243(2) 0.0327 1.0000 Uani . . . . O101 O 0.46809(19) 0.75062(18) 0.0993(2) 0.0315 1.0000 Uani . . . . O102 O 0.3230(2) 1.07071(18) 0.0763(3) 0.0412 1.0000 Uani . . . . N1 N 0.6906(3) 1.3122(2) 0.4772(3) 0.0324 1.0000 Uani . . . . N101 N 0.3119(2) 0.6850(2) 0.0246(2) 0.0298 1.0000 Uani . . . . C1 C 0.7209(3) 1.2297(2) 0.4674(3) 0.0245 1.0000 Uani . . . . C2 C 0.8169(3) 1.2102(3) 0.4831(3) 0.0318 1.0000 Uani . . . . C3 C 0.8507(3) 1.1276(3) 0.4733(3) 0.0375 1.0000 Uani . . . . C4 C 0.7890(3) 1.0593(3) 0.4503(3) 0.0303 1.0000 Uani . . . . C5 C 0.6952(2) 1.0762(2) 0.4358(2) 0.0214 1.0000 Uani . . . . C6 C 0.6594(2) 1.1613(2) 0.4414(2) 0.0193 1.0000 Uani . . . . C7 C 0.5611(3) 1.1776(2) 0.4176(2) 0.0222 1.0000 Uani . . . . C8 C 0.5002(2) 1.1036(2) 0.3870(2) 0.0191 1.0000 Uani . . . . C9 C 0.5315(2) 1.0185(2) 0.3875(2) 0.0184 1.0000 Uani . . . . C10 C 0.6306(2) 1.0007(2) 0.4154(2) 0.0208 1.0000 Uani . . . . C11 C 0.4074(3) 1.1248(2) 0.3592(2) 0.0248 1.0000 Uani . . . . C12 C 0.3458(3) 1.0619(2) 0.3324(3) 0.0254 1.0000 Uani . . . . C13 C 0.3729(2) 0.9740(2) 0.3339(2) 0.0234 1.0000 Uani . . . . C14 C 0.3073(3) 0.9089(3) 0.3073(3) 0.0268 1.0000 Uani . . . . C15 C 0.3309(3) 0.8238(3) 0.3064(3) 0.0282 1.0000 Uani . . . . C16 C 0.4236(3) 0.8005(2) 0.3321(3) 0.0293 1.0000 Uani . . . . C17 C 0.4901(3) 0.8604(2) 0.3588(3) 0.0256 1.0000 Uani . . . . C18 C 0.4674(2) 0.9503(2) 0.3599(2) 0.0205 1.0000 Uani . . . . C19 C 0.2602(3) 0.7559(3) 0.2763(3) 0.0357 1.0000 Uani . . . . C20 C 0.4952(4) 0.5445(5) 0.2331(5) 0.0619 0.758(5) Uani D P . . C101 C 0.2798(3) 0.7688(2) 0.0259(3) 0.0232 1.0000 Uani . . . . C102 C 0.1874(3) 0.7858(3) -0.0046(3) 0.0303 1.0000 Uani . . . . C103 C 0.1533(3) 0.8682(3) -0.0070(3) 0.0343 1.0000 Uani . . . . C104 C 0.2102(3) 0.9378(3) 0.0203(3) 0.0310 1.0000 Uani . . . . C105 C 0.3016(3) 0.9231(2) 0.0509(3) 0.0247 1.0000 Uani . . . . C106 C 0.3378(3) 0.8385(2) 0.0554(2) 0.0218 1.0000 Uani . . . . C107 C 0.4330(2) 0.8247(2) 0.0899(2) 0.0212 1.0000 Uani . . . . C108 C 0.4919(2) 0.9009(2) 0.1172(2) 0.0205 1.0000 Uani . . . . C109 C 0.4584(2) 0.9862(2) 0.1124(2) 0.0201 1.0000 Uani . . . . C110 C 0.3592(3) 0.9988(2) 0.0797(3) 0.0247 1.0000 Uani . . . . C111 C 0.5846(2) 0.8842(2) 0.1480(2) 0.0242 1.0000 Uani . . . . C112 C 0.6437(3) 0.9504(3) 0.1735(3) 0.0275 1.0000 Uani . . . . C113 C 0.6131(3) 1.0375(2) 0.1685(3) 0.0265 1.0000 Uani . . . . C114 C 0.6749(3) 1.1052(3) 0.1951(3) 0.0304 1.0000 Uani . . . . C115 C 0.6485(3) 1.1899(3) 0.1940(3) 0.0316 1.0000 Uani . . . . C116 C 0.5542(3) 1.2095(3) 0.1655(3) 0.0329 1.0000 Uani . . . . C117 C 0.4922(3) 1.1453(2) 0.1390(3) 0.0265 1.0000 Uani . . . . C118 C 0.5193(3) 1.0563(2) 0.1400(2) 0.0231 1.0000 Uani . . . . C119 C 0.7142(4) 1.2618(3) 0.2232(3) 0.0407 1.0000 Uani . . . . H11 H 0.6344 1.3244 0.4593 0.0388 1.0000 Uiso R . . . H12 H 0.7282 1.3507 0.4992 0.0385 1.0000 Uiso R . . . H21 H 0.8577 1.2552 0.4997 0.0390 1.0000 Uiso R . . . H31 H 0.9145 1.1168 0.4810 0.0456 1.0000 Uiso R . . . H41 H 0.8117 1.0028 0.4441 0.0367 1.0000 Uiso R . . . H111 H 0.3894 1.1820 0.3611 0.0300 1.0000 Uiso R . . . H121 H 0.2855 1.0779 0.3125 0.0308 1.0000 Uiso R . . . H141 H 0.2471 0.9244 0.2892 0.0331 1.0000 Uiso R . . . H161 H 0.4425 0.7430 0.3308 0.0365 1.0000 Uiso R . . . H171 H 0.5507 0.8424 0.3764 0.0304 1.0000 Uiso R . . . H191 H 0.2485 0.7178 0.3272 0.0550 1.0000 Uiso R . . . H192 H 0.2029 0.7829 0.2570 0.0548 1.0000 Uiso R . . . H193 H 0.2862 0.7237 0.2254 0.0538 1.0000 Uiso R . . . H201 H 0.5225 0.6015 0.2200 0.0697 0.758(5) Uiso R P . . H1011 H 0.2719 0.6453 0.0141 0.0371 1.0000 Uiso R . . . H1012 H 0.3654 0.6739 0.0525 0.0356 1.0000 Uiso R . . . H1021 H 0.1496 0.7389 -0.0213 0.0361 1.0000 Uiso R . . . H1031 H 0.0919 0.8793 -0.0266 0.0410 1.0000 Uiso R . . . H1041 H 0.1869 0.9942 0.0159 0.0380 1.0000 Uiso R . . . H1111 H 0.6060 0.8277 0.1513 0.0285 1.0000 Uiso R . . . H1121 H 0.7044 0.9365 0.1957 0.0342 1.0000 Uiso R . . . H1141 H 0.7364 1.0913 0.2143 0.0370 1.0000 Uiso R . . . H1161 H 0.5331 1.2673 0.1633 0.0390 1.0000 Uiso R . . . H1171 H 0.4316 1.1611 0.1197 0.0315 1.0000 Uiso R . . . H1191 H 0.6874 1.2902 0.2761 0.0618 1.0000 Uiso R . . . H1192 H 0.7213 1.3012 0.1729 0.0620 1.0000 Uiso R . . . H1193 H 0.7738 1.2360 0.2378 0.0611 1.0000 Uiso 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 Cl1 0.0547(9) 0.0759(13) 0.0472(9) -0.0174(8) 0.0000(8) -0.0321(9) Cl3 0.0481(8) 0.0422(8) 0.0533(9) -0.0101(7) 0.0044(7) 0.0055(7) Cl20 0.0217(18) 0.163(7) 0.062(2) -0.041(3) -0.0085(17) 0.003(3) Cl21 0.050(5) 0.131(7) 0.47(3) -0.016(9) -0.088(8) 0.037(5) O1 0.0271(13) 0.0176(12) 0.0507(17) -0.0069(12) -0.0069(13) 0.0036(11) O2 0.0284(14) 0.0189(14) 0.0510(17) -0.0019(12) -0.0112(12) 0.0038(11) O101 0.0220(12) 0.0235(13) 0.0492(17) -0.0039(12) -0.0056(12) 0.0023(11) O102 0.0359(16) 0.0207(15) 0.067(2) -0.0059(14) -0.0237(15) 0.0080(12) N1 0.0310(17) 0.0210(17) 0.045(2) -0.0063(14) -0.0046(15) -0.0073(14) N101 0.0305(17) 0.0212(17) 0.0378(18) -0.0070(13) -0.0023(14) -0.0075(13) C1 0.0259(17) 0.0238(19) 0.0239(18) 0.0003(14) 0.0004(14) -0.0087(15) C2 0.0240(19) 0.032(2) 0.040(2) -0.0008(17) -0.0052(16) -0.0103(16) C3 0.0172(17) 0.040(2) 0.056(3) 0.008(2) -0.0074(18) -0.0071(17) C4 0.0248(18) 0.0217(18) 0.045(2) 0.0009(17) -0.0008(16) 0.0001(15) C5 0.0154(16) 0.0234(19) 0.0256(17) 0.0016(13) 0.0015(12) -0.0004(13) C6 0.0199(16) 0.0164(17) 0.0217(17) -0.0005(12) -0.0011(13) -0.0063(13) C7 0.0248(17) 0.0179(17) 0.0238(16) -0.0034(13) -0.0009(14) -0.0023(14) C8 0.0179(15) 0.0188(16) 0.0206(16) 0.0004(12) -0.0028(12) -0.0015(13) C9 0.0189(15) 0.0172(16) 0.0191(15) -0.0019(12) -0.0018(12) -0.0017(13) C10 0.0217(17) 0.0180(16) 0.0228(16) -0.0002(14) -0.0031(13) 0.0014(13) C11 0.0225(16) 0.0240(17) 0.0280(18) 0.0024(14) -0.0041(15) 0.0060(14) C12 0.0181(15) 0.0254(18) 0.0326(19) -0.0023(15) -0.0032(14) 0.0017(14) C13 0.0215(16) 0.0290(18) 0.0198(16) -0.0011(14) 0.0000(13) -0.0053(14) C14 0.0220(16) 0.0294(18) 0.0290(18) -0.0016(15) -0.0059(15) -0.0048(15) C15 0.0312(18) 0.0304(19) 0.0230(17) 0.0011(15) -0.0030(15) -0.0090(16) C16 0.037(2) 0.0236(18) 0.0273(18) -0.0035(15) -0.0009(15) -0.0067(16) C17 0.0289(18) 0.0208(17) 0.0271(18) 0.0028(13) -0.0040(14) -0.0041(14) C18 0.0217(16) 0.0201(16) 0.0198(15) 0.0010(13) -0.0029(13) -0.0039(14) C19 0.039(2) 0.033(2) 0.035(2) -0.0049(17) -0.0058(18) -0.0168(18) C20 0.056(4) 0.069(5) 0.062(4) -0.025(4) 0.009(3) -0.032(4) C101 0.0207(16) 0.0257(19) 0.0231(17) -0.0043(14) -0.0001(13) -0.0037(15) C102 0.0201(18) 0.029(2) 0.042(2) 0.0029(17) -0.0079(15) -0.0116(15) C103 0.0148(16) 0.032(2) 0.056(3) -0.0015(19) -0.0054(16) -0.0002(15) C104 0.0210(17) 0.0242(19) 0.048(2) 0.0004(17) -0.0017(16) 0.0013(15) C105 0.0203(17) 0.025(2) 0.0287(18) 0.0013(14) -0.0025(14) 0.0021(15) C106 0.0211(17) 0.0214(18) 0.0230(17) 0.0030(13) -0.0020(13) -0.0046(14) C107 0.0199(17) 0.0195(17) 0.0242(16) -0.0011(14) 0.0000(13) 0.0011(13) C108 0.0183(15) 0.0208(17) 0.0224(17) 0.0000(13) -0.0045(12) -0.0024(13) C109 0.0227(16) 0.0175(16) 0.0201(15) 0.0005(12) -0.0014(13) -0.0028(13) C110 0.0245(18) 0.0246(19) 0.0249(17) 0.0019(15) -0.0016(14) 0.0013(15) C111 0.0177(15) 0.0267(18) 0.0283(18) 0.0013(15) -0.0010(13) 0.0047(14) C112 0.0188(16) 0.038(2) 0.0255(18) 0.0026(16) -0.0045(14) -0.0025(15) C113 0.0292(18) 0.0293(19) 0.0210(17) -0.0013(14) -0.0027(14) -0.0056(15) C114 0.0278(18) 0.040(2) 0.0232(17) 0.0001(16) -0.0025(15) -0.0154(17) C115 0.038(2) 0.035(2) 0.0216(17) -0.0026(16) 0.0006(16) -0.0153(18) C116 0.046(2) 0.0235(18) 0.0294(18) -0.0022(16) 0.0011(17) -0.0129(17) C117 0.0299(18) 0.0207(17) 0.0289(19) -0.0008(14) -0.0018(15) -0.0024(15) C118 0.0266(17) 0.0219(17) 0.0207(15) -0.0026(13) 0.0019(13) -0.0052(15) C119 0.053(2) 0.036(2) 0.034(2) -0.0052(17) -0.005(2) -0.023(2) loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' Cl 0.1484 0.1585 11.4604 0.0104 7.1964 1.1662 6.2556 18.5194 1.6455 47.7784 -9.5574 'International Tables Vol C 4.2.6.8 and 6.1.1.4' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag C1 N1 H11 118.1 no C1 N1 H12 119.7 no H11 N1 H12 122.1 no C101 N101 H1011 117.7 no C101 N101 H1012 117.7 no H1011 N101 H1012 121.2 no N1 C1 C2 119.4(3) yes N1 C1 C6 122.4(3) yes C2 C1 C6 118.2(4) yes C1 C2 C3 121.3(3) yes C1 C2 H21 118.4 no C3 C2 H21 120.3 no C2 C3 C4 120.4(4) yes C2 C3 H31 119.8 no C4 C3 H31 119.7 no C3 C4 C5 119.5(4) yes C3 C4 H41 120.8 no C5 C4 H41 119.7 no C4 C5 C6 121.2(3) yes C4 C5 C10 117.9(3) yes C6 C5 C10 121.0(3) yes C1 C6 C5 119.3(3) yes C1 C6 C7 121.2(3) yes C5 C6 C7 119.4(3) yes C6 C7 O1 122.6(3) yes C6 C7 C8 119.1(3) yes O1 C7 C8 118.3(3) yes C7 C8 C9 122.7(3) yes C7 C8 C11 116.1(3) yes C9 C8 C11 121.2(3) yes C8 C9 C10 118.6(3) yes C8 C9 C18 119.4(3) yes C10 C9 C18 122.0(3) yes C5 C10 C9 118.6(3) yes C5 C10 O2 117.4(3) yes C9 C10 O2 123.9(3) yes C8 C11 C12 120.6(3) yes C8 C11 H111 118.2 no C12 C11 H111 121.2 no C11 C12 C13 120.7(3) yes C11 C12 H121 118.8 no C13 C12 H121 120.5 no C12 C13 C14 120.1(3) yes C12 C13 C18 120.2(3) yes C14 C13 C18 119.7(3) yes C13 C14 C15 121.9(3) yes C13 C14 H141 119.6 no C15 C14 H141 118.4 no C14 C15 C16 118.3(3) yes C14 C15 C19 120.9(4) yes C16 C15 C19 120.8(4) yes C15 C16 C17 122.5(4) yes C15 C16 H161 120.5 no C17 C16 H161 117.0 no C16 C17 C18 120.3(4) yes C16 C17 H171 120.1 no C18 C17 H171 119.6 no C9 C18 C13 117.9(3) yes C9 C18 C17 124.9(3) yes C13 C18 C17 117.2(3) yes C15 C19 H191 108.9 no C15 C19 H192 109.9 no H191 C19 H192 110.3 no C15 C19 H193 108.9 no H191 C19 H193 109.4 no H192 C19 H193 109.3 no Cl1 C20 Cl3 109.2(3) yes Cl1 C20 Cl20 112.8(4) yes Cl3 C20 Cl20 114.1(5) yes Cl1 C20 H201 109.9 no Cl3 C20 H201 108.5 no Cl20 C20 H201 102.0 no Cl21 C20 Cl1 109.9(6) yes Cl21 C20 Cl3 105.6(6) yes Cl1 C20 Cl3 109.2(3) yes Cl21 C20 H201 113.5 no Cl1 C20 H201 109.9 no Cl3 C20 H201 108.5 no N101 C101 C102 118.7(3) yes N101 C101 C106 122.0(3) yes C102 C101 C106 119.2(4) yes C101 C102 C103 120.9(3) yes C101 C102 H1021 117.9 no C103 C102 H1021 121.2 no C102 C103 C104 120.5(3) yes C102 C103 H1031 120.8 no C104 C103 H1031 118.7 no C103 C104 C105 119.9(4) yes C103 C104 H1041 119.7 no C105 C104 H1041 120.3 no C104 C105 C106 120.4(3) yes C104 C105 C110 118.1(3) yes C106 C105 C110 121.5(3) yes C101 C106 C105 118.9(3) yes C101 C106 C107 121.8(3) yes C105 C106 C107 119.3(3) yes C106 C107 O101 122.5(3) yes C106 C107 C108 119.4(3) yes O101 C107 C108 118.1(3) yes C107 C108 C109 122.7(3) yes C107 C108 C111 117.2(3) yes C109 C108 C111 120.1(3) yes C108 C109 C110 117.1(3) yes C108 C109 C118 119.5(3) yes C110 C109 C118 123.4(3) yes C109 C110 C105 120.0(3) yes C109 C110 O102 121.6(3) yes C105 C110 O102 118.4(3) yes C108 C111 C112 121.0(3) yes C108 C111 H1111 119.5 no C112 C111 H1111 119.6 no C111 C112 C113 120.7(3) yes C111 C112 H1121 118.4 no C113 C112 H1121 120.8 no C112 C113 C114 120.1(4) yes C112 C113 C118 119.6(3) yes C114 C113 C118 120.2(4) yes C113 C114 C115 122.6(4) yes C113 C114 H1141 118.7 no C115 C114 H1141 118.6 no C114 C115 C116 117.6(3) yes C114 C115 C119 122.5(4) yes C116 C115 C119 119.9(4) yes C115 C116 C117 121.4(4) yes C115 C116 H1161 120.4 no C117 C116 H1161 118.2 no C116 C117 C118 121.3(4) yes C116 C117 H1171 118.5 no C118 C117 H1171 120.1 no C109 C118 C117 124.2(3) yes C109 C118 C113 119.0(3) yes C117 C118 C113 116.8(3) yes C115 C119 H1191 108.4 no C115 C119 H1192 109.0 no H1191 C119 H1192 110.7 no C115 C119 H1193 107.1 no H1191 C119 H1193 111.5 no H1192 C119 H1193 110.0 no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance _geom_bond_publ_flag Cl1 C20 1.772(7) yes Cl3 C20 1.720(8) yes Cl20 C20 1.689(8) yes Cl21 C20 1.827(8) yes O1 C7 1.241(4) yes O2 C10 1.217(4) yes O101 C107 1.257(4) yes O102 C110 1.226(5) yes N1 C1 1.354(5) yes N1 H11 0.857 no N1 H12 0.860 no N101 C101 1.374(5) yes N101 H1011 0.848 no N101 H1012 0.874 no C1 C2 1.409(5) yes C1 C6 1.420(5) yes C2 C3 1.371(6) yes C2 H21 0.936 no C3 C4 1.410(6) yes C3 H31 0.925 no C4 C5 1.369(5) yes C4 H41 0.936 no C5 C6 1.413(5) yes C5 C10 1.513(5) yes C6 C7 1.454(5) yes C7 C8 1.499(5) yes C8 C9 1.389(5) yes C8 C11 1.411(5) yes C9 C10 1.484(5) yes C9 C18 1.448(5) yes C11 C12 1.361(5) yes C11 H111 0.922 no C12 C13 1.413(5) yes C12 H121 0.934 no C13 C14 1.422(5) yes C13 C18 1.436(5) yes C14 C15 1.359(6) yes C14 H141 0.921 no C15 C16 1.409(6) yes C15 C19 1.514(5) yes C16 C17 1.376(5) yes C16 H161 0.930 no C17 C18 1.428(5) yes C17 H171 0.936 no C19 H191 0.955 no C19 H192 0.954 no C19 H193 0.959 no C20 H201 0.981 no C20 H201 0.981 no C101 C102 1.403(5) yes C101 C106 1.420(5) yes C102 C103 1.364(6) yes C102 H1021 0.933 no C103 C104 1.401(6) yes C103 H1031 0.929 no C104 C105 1.385(5) yes C104 H1041 0.934 no C105 C106 1.407(5) yes C105 C110 1.486(5) yes C106 C107 1.451(5) yes C107 C108 1.496(5) yes C108 C109 1.404(5) yes C108 C111 1.408(5) yes C109 C110 1.493(5) yes C109 C118 1.441(5) yes C111 C112 1.371(5) yes C111 H1111 0.927 no C112 C113 1.417(6) yes C112 H1121 0.941 no C113 C114 1.417(5) yes C113 C118 1.419(5) yes C114 C115 1.362(6) yes C114 H1141 0.937 no C115 C116 1.429(6) yes C115 C119 1.510(5) yes C116 C117 1.378(5) yes C116 H1161 0.944 no C117 C118 1.431(5) yes C117 H1171 0.932 no C119 H1191 0.958 no C119 H1192 0.952 no C119 H1193 0.956 no loop_ _oxford_twin_element_scale_factors 0.5414(18) 0.4586(18) _journal_paper_doi 10.1021/ol9020496