#------------------------------------------------------------------------------ #$Date: 2021-12-03 03:36:38 +0200 (Fri, 03 Dec 2021) $ #$Revision: 270996 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/15/84/7158426.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_7158426 loop_ _publ_author_name 'Sartucci, Jenna L.' 'Maity, Arindam' 'Mohanan, Manikandan' 'Bertke, Jeffery A.' 'Kertesz, Miklos' 'Gavvalapalli, Nagarjuna' _publ_section_title ; Molecular Tetrominoes: Selective Masking of Donor pi-face to Control Configuration of Donor-Acceptor Complex ; _journal_name_full 'Organic & Biomolecular Chemistry' _journal_paper_doi 10.1039/D1OB02293H _journal_year 2021 _chemical_formula_moiety 'C22 H14, 2(C8 Cl2 N2 O2)' _chemical_formula_sum 'C38 H14 Cl4 N4 O4' _chemical_formula_weight 732.33 _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary intrinsic _audit_creation_method SHELXL-2018/3 _audit_update_record ; 2021-05-25 deposited with the CCDC. 2021-11-26 downloaded from the CCDC. ; _cell_angle_alpha 92.211(8) _cell_angle_beta 97.288(8) _cell_angle_gamma 102.060(7) _cell_formula_units_Z 1 _cell_length_a 6.4871(13) _cell_length_b 7.1989(15) _cell_length_c 17.900(4) _cell_measurement_reflns_used 9914 _cell_measurement_temperature 100(2) _cell_measurement_theta_max 26.33 _cell_measurement_theta_min 2.30 _cell_volume 809.0(3) _computing_cell_refinement 'SAINT V8.37A (Bruker, 2005)' _computing_data_collection 'APEX3 V2016.5-0 (Bruker, 2016)' _computing_data_reduction ; SAINT V8.37A, XPREP v2014/2, SADABS V2016/2 (Bruker, 2016) ; _computing_molecular_graphics 'SHELXLE v932 (Hubschle, 2011)' _computing_publication_material 'XCIF V2014-2 (Bruker, 2014)' _computing_structure_refinement 'SHELX-2018-3 (Sheldrick, 2015)' _computing_structure_solution 'SHELX-2014-5 (Sheldrick, 2015)' _diffrn_ambient_temperature 100(2) _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.998 _diffrn_measurement_device 'Bruker D8 Quest/Photon 100' _diffrn_measurement_method 'profile data from \f and \w scans' _diffrn_radiation_monochromator 'multilayer mirrors' _diffrn_radiation_source 'microfocus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0589 _diffrn_reflns_av_unetI/netI 0.0229 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.998 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_number 44132 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.998 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 26.420 _diffrn_reflns_theta_min 2.299 _exptl_absorpt_coefficient_mu 0.416 _exptl_absorpt_correction_T_max 0.99019 _exptl_absorpt_correction_T_min 0.91231 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'SADABS V2016/2 (Bruker, 2016)' _exptl_crystal_colour green _exptl_crystal_density_diffrn 1.503 _exptl_crystal_density_method 'not measured' _exptl_crystal_description plate _exptl_crystal_F_000 370 _exptl_crystal_size_max 0.312 _exptl_crystal_size_mid 0.204 _exptl_crystal_size_min 0.036 _refine_diff_density_max 0.182 _refine_diff_density_min -0.192 _refine_diff_density_rms 0.044 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.074 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 353 _refine_ls_number_reflns 3310 _refine_ls_number_restraints 430 _refine_ls_restrained_S_all 1.014 _refine_ls_R_factor_all 0.0428 _refine_ls_R_factor_gt 0.0327 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0443P)^2^+0.2093P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0816 _refine_ls_wR_factor_ref 0.0877 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2778 _reflns_number_total 3310 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d1ob02293h3.cif _cod_data_source_block B19324_a _cod_original_cell_volume 809.1(3) _cod_database_code 7158426 _shelx_shelxl_version_number 2018/3 _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. ; _shelx_estimated_absorpt_t_min 0.881 _shelx_estimated_absorpt_t_max 0.985 _shelx_res_file ; TITL B19324_a.res in P-1 B19324_a.res created by SHELXL-2018/3 at 11:11:36 on 21-Aug-2019 REM Old TITL B19324 in P-1 REM SHELXT solution in P-1 REM R1 0.267, Rweak 0.012, Alpha 0.064, Orientation as input REM Formula found by SHELXT: C16 Cl3 N O3 CELL 0.71073 6.4871 7.1989 17.9001 92.211 97.288 102.060 ZERR 1.000 0.0013 0.0015 0.0038 0.008 0.008 0.007 LATT 1 SFAC C H CL N O UNIT 38 14 4 4 4 TEMP -173.110 SIZE 0.036 0.204 0.312 L.S. 20 BOND $H LIST 4 FMAP 2 OMIT -3 0 3 CONF ACTA SIMU 0.01 0.02 CL1 > C19B PLAN 20 WGHT 0.044300 0.209300 FVAR 0.78282 0.60208 C1 1 0.269175 0.875080 0.791117 11.00000 0.03138 0.01418 = 0.02350 0.00085 0.00485 0.00366 C2 1 0.484483 0.926302 0.821044 11.00000 0.03048 0.01962 = 0.03062 0.00355 0.00881 0.00102 AFIX 43 H2 2 0.586174 0.986040 0.790832 11.00000 -1.20000 AFIX 0 C3 1 0.549292 0.890171 0.894367 11.00000 0.03009 0.02694 = 0.03436 0.00256 0.00121 0.00151 AFIX 43 H3 2 0.695646 0.925228 0.914681 11.00000 -1.20000 AFIX 0 C4 1 0.401147 0.802686 0.938561 11.00000 0.04270 0.02333 = 0.02418 0.00313 0.00125 0.00268 AFIX 43 H4 2 0.446594 0.777644 0.989022 11.00000 -1.20000 AFIX 0 C5 1 0.188136 0.751837 0.909627 11.00000 0.03823 0.02029 = 0.02656 0.00184 0.01131 0.00072 AFIX 43 H5 2 0.087604 0.692325 0.940297 11.00000 -1.20000 AFIX 0 C6 1 0.120385 0.787141 0.836173 11.00000 0.02794 0.01873 = 0.02941 -0.00023 0.00576 0.00043 AFIX 43 H6 2 -0.026322 0.751952 0.816345 11.00000 -1.20000 AFIX 0 C7 1 0.201659 0.912194 0.715030 11.00000 0.03406 0.01669 = 0.02824 0.00016 0.00675 0.00280 C8 1 0.146219 0.940153 0.650653 11.00000 0.03414 0.01775 = 0.02781 0.00133 0.00681 0.00235 C9 1 0.073416 0.969664 0.574169 11.00000 0.03434 0.01593 = 0.02443 0.00187 0.00503 0.00317 C10 1 0.213546 1.068308 0.528505 11.00000 0.02910 0.02118 = 0.02902 0.00181 0.00369 -0.00046 AFIX 43 H10 2 0.359249 1.114677 0.548056 11.00000 -1.20000 AFIX 0 C11 1 -0.140057 0.901866 0.544834 11.00000 0.03303 0.02125 = 0.02731 0.00541 0.00759 -0.00079 AFIX 43 H11 2 -0.235537 0.834659 0.575584 11.00000 -1.20000 AFIX 0 PART 1 21 CL1 3 -0.111633 0.394087 0.598029 21.00000 0.02278 0.03111 = 0.02561 0.00205 -0.00117 0.00533 CL2 3 0.362664 0.578422 0.579287 21.00000 0.03080 0.02757 = 0.02007 0.00569 0.00648 0.00386 O1 5 0.648693 0.597763 0.720733 21.00000 0.01928 0.01527 = 0.03480 0.00885 0.00465 0.00320 O2 5 -0.143992 0.247836 0.746957 21.00000 0.02218 0.03182 = 0.03591 0.00900 0.00742 0.00067 N1 4 0.716755 0.447421 0.906015 21.00000 0.03441 0.03711 = 0.03048 0.00455 0.00593 0.00323 N2 4 0.108811 0.216196 0.929746 21.00000 0.03998 0.03696 = 0.03580 0.00975 0.01488 0.00688 C12 1 0.091225 0.409468 0.668340 21.00000 0.02270 0.01620 = 0.01734 0.00448 0.00186 0.00643 C13 1 0.294795 0.490851 0.660618 21.00000 0.02314 0.01432 = 0.01425 0.00507 0.00482 0.00369 C14 1 0.469148 0.508376 0.723590 21.00000 0.02412 0.01544 = 0.01915 0.00542 0.00673 0.00458 C15 1 0.413166 0.425213 0.795222 21.00000 0.02286 0.01735 = 0.02001 0.00241 -0.00072 0.00755 C16 1 0.210968 0.342755 0.802888 21.00000 0.02622 0.01702 = 0.01763 0.00479 0.00542 0.00545 C17 1 0.035514 0.327318 0.739431 21.00000 0.02072 0.01638 = 0.01904 0.00370 0.00152 0.00533 C18 1 0.582350 0.436565 0.855565 21.00000 0.02979 0.02356 = 0.02859 0.00311 0.01077 0.00216 C19 1 0.153660 0.270694 0.872616 21.00000 0.02729 0.02413 = 0.02347 0.00399 0.00487 0.00667 PART 2 -21 SAME 0.01 CL1 > C19 CL1B 3 0.183596 0.252207 0.909763 -21.00000 0.02996 0.02428 = 0.02617 0.00612 0.00742 0.00531 CL2B 3 0.653150 0.442265 0.880813 -21.00000 0.02858 0.02872 = 0.02660 0.00391 0.00307 0.00206 O1B 5 0.659929 0.560928 0.726305 -21.00000 0.02337 0.01102 = 0.03459 0.00936 0.00502 0.00515 O2B 5 -0.120177 0.228251 0.773589 -21.00000 0.02031 0.03134 = 0.03360 0.00333 0.00722 -0.00395 N1B 4 0.377412 0.607087 0.553488 -21.00000 0.02217 0.03394 = 0.02986 0.00485 0.00496 0.00323 N2B 4 -0.229999 0.330209 0.589328 -21.00000 0.02797 0.03856 = 0.03453 0.00191 0.00055 0.00552 C12B 1 0.240473 0.335633 0.826060 -21.00000 0.02494 0.01522 = 0.01523 0.00050 0.00017 0.00498 C13B 1 0.440012 0.417403 0.813963 -21.00000 0.01982 0.01538 = 0.01622 0.00549 0.00089 0.00283 C14B 1 0.481876 0.495328 0.741020 -21.00000 0.01850 0.01662 = 0.02084 0.00249 -0.00293 0.00659 C15B 1 0.296891 0.472624 0.680662 -21.00000 0.02874 0.01471 = 0.01680 0.00826 0.00847 0.00497 C16B 1 0.098934 0.383161 0.691543 -21.00000 0.01963 0.01618 = 0.01653 0.00390 -0.00095 0.00500 C17B 1 0.059370 0.308291 0.765478 -21.00000 0.02635 0.01709 = 0.01593 0.00628 0.00468 0.00826 C18B 1 0.341826 0.550231 0.610989 -21.00000 0.02178 0.02660 = 0.02197 0.00129 0.00047 0.00651 C19B 1 -0.080282 0.357703 0.634107 -21.00000 0.02212 0.02583 = 0.02652 0.00622 0.00531 0.00713 PART 0 HKLF 4 REM B19324_a.res in P-1 REM wR2 = 0.087712, GooF = S = 1.07372, Restrained GooF = 1.01408 for all data REM R1 = 0.032725 for 2778 Fo > 4sig(Fo) and 0.042782 for all 3310 data REM 353 parameters refined using 430 restraints END WGHT 0.0443 0.2093 REM Highest difference peak 0.182, deepest hole -0.192, 1-sigma level 0.044 Q1 1 0.1362 1.0309 0.5518 11.00000 0.05 0.18 Q2 1 0.1529 1.1032 0.4995 11.00000 0.05 0.17 Q3 1 0.5487 1.2550 0.5425 11.00000 0.05 0.17 Q4 1 0.7630 0.4507 0.9587 11.00000 0.05 0.16 Q5 1 0.4631 0.8686 0.9127 11.00000 0.05 0.16 Q6 1 -0.2931 0.2640 0.5332 11.00000 0.05 0.15 Q7 1 0.3684 0.8954 0.8020 11.00000 0.05 0.15 Q8 1 0.7137 0.4084 0.8372 11.00000 0.05 0.15 Q9 1 0.8397 0.4431 0.8182 11.00000 0.05 0.15 Q10 1 0.2091 0.7906 0.8091 11.00000 0.05 0.14 Q11 1 -0.1442 0.3993 0.5108 11.00000 0.05 0.14 Q12 1 0.8242 0.5555 0.8569 11.00000 0.05 0.14 Q13 1 0.1866 0.8763 0.8192 11.00000 0.05 0.14 Q14 1 0.1832 0.5815 0.5198 11.00000 0.05 0.14 Q15 1 0.7579 0.5668 0.7914 11.00000 0.05 0.14 Q16 1 0.1788 0.1343 1.0018 11.00000 0.05 0.14 Q17 1 0.1255 0.5204 0.9811 11.00000 0.05 0.14 Q18 1 -0.0268 0.5951 0.8992 11.00000 0.05 0.14 Q19 1 0.1095 0.9489 0.6075 11.00000 0.05 0.14 Q20 1 0.6127 0.9325 0.7612 11.00000 0.05 0.14 ; _shelx_res_checksum 32341 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, -z' 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 C1 C 0.2692(2) 0.87508(17) 0.79112(7) 0.0231(3) Uani 1 1 d . . . . . C2 C 0.4845(2) 0.92630(18) 0.82104(8) 0.0271(3) Uani 1 1 d . . . . . H2 H 0.586174 0.986040 0.790832 0.033 Uiso 1 1 calc R U . . . C3 C 0.5493(2) 0.8902(2) 0.89437(8) 0.0314(3) Uani 1 1 d . . . . . H3 H 0.695646 0.925228 0.914681 0.038 Uiso 1 1 calc R U . . . C4 C 0.4011(2) 0.80269(19) 0.93856(8) 0.0310(3) Uani 1 1 d . . . . . H4 H 0.446594 0.777644 0.989022 0.037 Uiso 1 1 calc R U . . . C5 C 0.1881(2) 0.75184(19) 0.90963(8) 0.0286(3) Uani 1 1 d . . . . . H5 H 0.087604 0.692325 0.940297 0.034 Uiso 1 1 calc R U . . . C6 C 0.1204(2) 0.78714(18) 0.83617(8) 0.0259(3) Uani 1 1 d . . . . . H6 H -0.026322 0.751952 0.816345 0.031 Uiso 1 1 calc R U . . . C7 C 0.2017(2) 0.91219(18) 0.71503(8) 0.0265(3) Uani 1 1 d . . . . . C8 C 0.1462(2) 0.94015(18) 0.65065(8) 0.0268(3) Uani 1 1 d . . . . . C9 C 0.0734(2) 0.96966(17) 0.57417(7) 0.0251(3) Uani 1 1 d . . . . . C10 C 0.2135(2) 1.06831(18) 0.52851(8) 0.0273(3) Uani 1 1 d . . . . . H10 H 0.359249 1.114677 0.548056 0.033 Uiso 1 1 calc R U . . . C11 C -0.1401(2) 0.90187(18) 0.54483(8) 0.0278(3) Uani 1 1 d . . . . . H11 H -0.235537 0.834659 0.575584 0.033 Uiso 1 1 calc R U . . . Cl1 Cl -0.11163(14) 0.39409(10) 0.59803(5) 0.0270(2) Uani 0.6021(19) 1 d D U P A 1 Cl2 Cl 0.3627(2) 0.57842(17) 0.57929(7) 0.0261(4) Uani 0.6021(19) 1 d D U P A 1 O1 O 0.6487(10) 0.5978(12) 0.7207(8) 0.0229(12) Uani 0.6021(19) 1 d D U P A 1 O2 O -0.1440(6) 0.2478(6) 0.74696(18) 0.0302(7) Uani 0.6021(19) 1 d D U P A 1 N1 N 0.7168(8) 0.4474(9) 0.9060(3) 0.0345(10) Uani 0.6021(19) 1 d D U P A 1 N2 N 0.1088(6) 0.2162(4) 0.92975(18) 0.0367(7) Uani 0.6021(19) 1 d D U P A 1 C12 C 0.0912(8) 0.4095(7) 0.6683(2) 0.0184(8) Uani 0.6021(19) 1 d D U P A 1 C13 C 0.2948(10) 0.4909(11) 0.6606(3) 0.0170(10) Uani 0.6021(19) 1 d D U P A 1 C14 C 0.4691(9) 0.5084(14) 0.7236(4) 0.0191(11) Uani 0.6021(19) 1 d D U P A 1 C15 C 0.4132(10) 0.4252(13) 0.7952(3) 0.0199(10) Uani 0.6021(19) 1 d D U P A 1 C16 C 0.2110(8) 0.3428(8) 0.8029(2) 0.0199(9) Uani 0.6021(19) 1 d D U P A 1 C17 C 0.0355(6) 0.3273(6) 0.73943(19) 0.0186(8) Uani 0.6021(19) 1 d D U P A 1 C18 C 0.5823(8) 0.4366(9) 0.8556(3) 0.0272(12) Uani 0.6021(19) 1 d D U P A 1 C19 C 0.1537(5) 0.2707(4) 0.8726(2) 0.0246(6) Uani 0.6021(19) 1 d D U P A 1 Cl1B Cl 0.1836(2) 0.25221(17) 0.90976(9) 0.0264(3) Uani 0.3979(19) 1 d D U P A 2 Cl2B Cl 0.6531(3) 0.4423(2) 0.88081(10) 0.0286(6) Uani 0.3979(19) 1 d D U P A 2 O1B O 0.6599(15) 0.5609(19) 0.7263(12) 0.0225(17) Uani 0.3979(19) 1 d D U P A 2 O2B O -0.1202(9) 0.2283(9) 0.7736(3) 0.0295(11) Uani 0.3979(19) 1 d D U P A 2 N1B N 0.3774(15) 0.6071(13) 0.5535(4) 0.0289(15) Uani 0.3979(19) 1 d D U P A 2 N2B N -0.2300(7) 0.3302(6) 0.58933(19) 0.0343(8) Uani 0.3979(19) 1 d D U P A 2 C12B C 0.2405(12) 0.3356(13) 0.8261(3) 0.0186(13) Uani 0.3979(19) 1 d D U P A 2 C13B C 0.4400(15) 0.4174(19) 0.8140(5) 0.0173(15) Uani 0.3979(19) 1 d D U P A 2 C14B C 0.4819(13) 0.495(2) 0.7410(6) 0.0187(17) Uani 0.3979(19) 1 d D U P A 2 C15B C 0.2969(16) 0.4726(18) 0.6807(5) 0.0194(15) Uani 0.3979(19) 1 d D U P A 2 C16B C 0.0989(11) 0.3832(10) 0.6915(3) 0.0175(13) Uani 0.3979(19) 1 d D U P A 2 C17B C 0.0594(9) 0.3083(9) 0.7655(3) 0.0190(11) Uani 0.3979(19) 1 d D U P A 2 C18B C 0.3418(10) 0.5502(10) 0.6110(3) 0.0235(14) Uani 0.3979(19) 1 d D U P A 2 C19B C -0.0803(6) 0.3577(6) 0.6341(3) 0.0242(8) Uani 0.3979(19) 1 d D U P A 2 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 0.0314(7) 0.0142(6) 0.0235(7) 0.0008(5) 0.0048(5) 0.0037(5) C2 0.0305(8) 0.0196(6) 0.0306(7) 0.0035(5) 0.0088(6) 0.0010(5) C3 0.0301(8) 0.0269(7) 0.0344(8) 0.0026(6) 0.0012(6) 0.0015(6) C4 0.0427(9) 0.0233(7) 0.0242(7) 0.0031(5) 0.0012(6) 0.0027(6) C5 0.0382(8) 0.0203(7) 0.0266(7) 0.0018(5) 0.0113(6) 0.0007(6) C6 0.0279(7) 0.0187(6) 0.0294(7) -0.0002(5) 0.0058(6) 0.0004(5) C7 0.0341(8) 0.0167(6) 0.0282(7) 0.0002(5) 0.0067(6) 0.0028(5) C8 0.0341(8) 0.0178(6) 0.0278(7) 0.0013(5) 0.0068(6) 0.0023(5) C9 0.0343(8) 0.0159(6) 0.0244(7) 0.0019(5) 0.0050(6) 0.0032(5) C10 0.0291(7) 0.0212(7) 0.0290(7) 0.0018(5) 0.0037(6) -0.0005(5) C11 0.0330(8) 0.0213(7) 0.0273(7) 0.0054(5) 0.0076(6) -0.0008(6) Cl1 0.0228(4) 0.0311(4) 0.0256(4) 0.0020(3) -0.0012(3) 0.0053(3) Cl2 0.0308(5) 0.0276(7) 0.0201(10) 0.0057(7) 0.0065(8) 0.0039(4) O1 0.0193(13) 0.015(3) 0.035(2) 0.009(2) 0.0047(12) 0.0032(13) O2 0.0222(13) 0.0318(12) 0.0359(19) 0.0090(14) 0.0074(13) 0.0007(9) N1 0.034(3) 0.0371(15) 0.030(3) 0.005(2) 0.0059(17) 0.0032(18) N2 0.0400(18) 0.0370(15) 0.0358(17) 0.0098(11) 0.0149(13) 0.0069(13) C12 0.0227(15) 0.0162(15) 0.0173(19) 0.0045(14) 0.0019(15) 0.0064(11) C13 0.0231(14) 0.0143(19) 0.014(3) 0.005(2) 0.0048(17) 0.0037(11) C14 0.0241(18) 0.0154(16) 0.019(3) 0.005(2) 0.0067(16) 0.0046(14) C15 0.0229(18) 0.0173(15) 0.020(2) 0.002(2) -0.0007(16) 0.0075(13) C16 0.026(2) 0.0170(12) 0.018(2) 0.0048(17) 0.0054(17) 0.0054(13) C17 0.0207(13) 0.0164(13) 0.019(2) 0.0037(15) 0.0015(14) 0.0053(10) C18 0.030(3) 0.0236(13) 0.029(3) 0.003(2) 0.011(2) 0.002(2) C19 0.0273(14) 0.0241(13) 0.0235(16) 0.0040(13) 0.0049(14) 0.0067(10) Cl1B 0.0300(8) 0.0243(5) 0.0262(9) 0.0061(5) 0.0074(6) 0.0053(5) Cl2B 0.0286(18) 0.0287(6) 0.0266(18) 0.0039(13) 0.0031(10) 0.0021(12) O1B 0.023(2) 0.011(4) 0.035(3) 0.009(3) 0.0050(19) 0.0052(18) O2B 0.0203(18) 0.031(2) 0.034(3) 0.003(2) 0.0072(19) -0.0039(14) N1B 0.022(2) 0.034(3) 0.030(4) 0.005(3) 0.005(3) 0.0032(19) N2B 0.028(2) 0.039(2) 0.035(2) 0.0019(15) 0.0006(16) 0.0055(18) C12B 0.025(2) 0.0152(18) 0.015(3) 0.001(2) 0.000(2) 0.0050(16) C13B 0.020(3) 0.0154(19) 0.016(3) 0.005(3) 0.001(2) 0.003(2) C14B 0.019(2) 0.017(3) 0.021(4) 0.002(3) -0.003(2) 0.0066(16) C15B 0.029(2) 0.015(2) 0.017(4) 0.008(3) 0.008(2) 0.0050(16) C16B 0.0196(19) 0.016(2) 0.017(3) 0.004(2) -0.001(2) 0.0050(16) C17B 0.026(2) 0.0171(18) 0.016(3) 0.006(2) 0.005(2) 0.0083(16) C18B 0.022(2) 0.027(3) 0.022(4) 0.001(3) 0.000(3) 0.0065(19) C19B 0.022(2) 0.0258(18) 0.027(2) 0.0062(17) 0.0053(18) 0.0071(15) 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' loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0.00 0.00 -1.00 0.0050 0.00 0.00 1.00 0.0180 0.00 1.00 0.00 0.1160 0.00 -1.00 0.00 0.1160 1.00 0.00 0.00 0.0850 -1.00 0.00 0.00 0.1090 2.00 2.00 -1.00 0.0890 -2.00 -2.00 1.00 0.0780 -1.00 2.00 1.00 0.1430 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 C2 C1 C6 119.55(12) . . ? C2 C1 C7 120.10(12) . . ? C6 C1 C7 120.35(13) . . ? C3 C2 C1 120.02(13) . . ? C3 C2 H2 120.0 . . ? C1 C2 H2 120.0 . . ? C2 C3 C4 120.10(14) . . ? C2 C3 H3 119.9 . . ? C4 C3 H3 119.9 . . ? C5 C4 C3 120.36(13) . . ? C5 C4 H4 119.8 . . ? C3 C4 H4 119.8 . . ? C4 C5 C6 120.28(13) . . ? C4 C5 H5 119.9 . . ? C6 C5 H5 119.9 . . ? C5 C6 C1 119.69(13) . . ? C5 C6 H6 120.2 . . ? C1 C6 H6 120.2 . . ? C8 C7 C1 178.69(15) . . ? C7 C8 C9 178.11(15) . . ? C11 C9 C10 119.50(13) . . ? C11 C9 C8 119.75(12) . . ? C10 C9 C8 120.74(13) . . ? C11 C10 C9 120.02(13) 2_576 . ? C11 C10 H10 120.0 2_576 . ? C9 C10 H10 120.0 . . ? C10 C11 C9 120.47(13) 2_576 . ? C10 C11 H11 119.8 2_576 . ? C9 C11 H11 119.8 . . ? C13 C12 C17 121.4(3) . . ? C13 C12 Cl1 122.4(3) . . ? C17 C12 Cl1 116.2(3) . . ? C12 C13 C14 121.5(4) . . ? C12 C13 Cl2 122.1(4) . . ? C14 C13 Cl2 116.3(4) . . ? O1 C14 C13 122.8(7) . . ? O1 C14 C15 119.9(8) . . ? C13 C14 C15 117.0(3) . . ? C16 C15 C18 121.2(5) . . ? C16 C15 C14 121.5(4) . . ? C18 C15 C14 117.3(5) . . ? C15 C16 C19 122.0(4) . . ? C15 C16 C17 121.2(4) . . ? C19 C16 C17 116.8(4) . . ? O2 C17 C12 122.7(3) . . ? O2 C17 C16 120.0(3) . . ? C12 C17 C16 117.3(3) . . ? N1 C18 C15 178.2(8) . . ? N2 C19 C16 178.6(4) . . ? C13B C12B C17B 121.4(5) . . ? C13B C12B Cl1B 122.9(5) . . ? C17B C12B Cl1B 115.7(5) . . ? C12B C13B C14B 121.2(6) . . ? C12B C13B Cl2B 122.8(6) . . ? C14B C13B Cl2B 116.0(6) . . ? O1B C14B C13B 123.4(11) . . ? O1B C14B C15B 119.2(11) . . ? C13B C14B C15B 117.0(5) . . ? C16B C15B C18B 122.4(6) . . ? C16B C15B C14B 121.8(6) . . ? C18B C15B C14B 115.8(7) . . ? C15B C16B C19B 122.7(5) . . ? C15B C16B C17B 120.4(5) . . ? C19B C16B C17B 116.9(5) . . ? O2B C17B C12B 123.0(5) . . ? O2B C17B C16B 119.0(5) . . ? C12B C17B C16B 118.0(4) . . ? N1B C18B C15B 177.7(10) . . ? N2B C19B C16B 176.8(5) . . ? 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 C2 1.398(2) . ? C1 C6 1.4016(19) . ? C1 C7 1.4296(19) . ? C2 C3 1.378(2) . ? C2 H2 0.9500 . ? C3 C4 1.387(2) . ? C3 H3 0.9500 . ? C4 C5 1.380(2) . ? C4 H4 0.9500 . ? C5 C6 1.383(2) . ? C5 H5 0.9500 . ? C6 H6 0.9500 . ? C7 C8 1.200(2) . ? C8 C9 1.4293(19) . ? C9 C11 1.395(2) . ? C9 C10 1.4008(19) . ? C10 C11 1.379(2) 2_576 ? C10 H10 0.9500 . ? C11 H11 0.9500 . ? Cl1 C12 1.684(4) . ? Cl2 C13 1.682(5) . ? O1 C14 1.216(5) . ? O2 C17 1.212(4) . ? N1 C18 1.161(5) . ? N2 C19 1.159(4) . ? C12 C13 1.355(7) . ? C12 C17 1.478(4) . ? C13 C14 1.474(6) . ? C14 C15 1.490(6) . ? C15 C16 1.348(7) . ? C15 C18 1.426(5) . ? C16 C19 1.433(5) . ? C16 C17 1.486(4) . ? Cl1B C12B 1.691(6) . ? Cl2B C13B 1.684(8) . ? O1B C14B 1.219(6) . ? O2B C17B 1.216(5) . ? N1B C18B 1.155(6) . ? N2B C19B 1.155(6) . ? C12B C13B 1.353(10) . ? C12B C17B 1.469(5) . ? C13B C14B 1.475(8) . ? C14B C15B 1.486(9) . ? C15B C16B 1.353(10) . ? C15B C18B 1.425(6) . ? C16B C19B 1.427(7) . ? C16B C17B 1.480(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 C6 C1 C2 C3 0.0(2) . . . . ? C7 C1 C2 C3 -179.91(13) . . . . ? C1 C2 C3 C4 0.1(2) . . . . ? C2 C3 C4 C5 -0.2(2) . . . . ? C3 C4 C5 C6 0.2(2) . . . . ? C4 C5 C6 C1 0.0(2) . . . . ? C2 C1 C6 C5 -0.08(19) . . . . ? C7 C1 C6 C5 179.88(12) . . . . ? C11 C9 C10 C11 0.1(2) . . . 2_576 ? C8 C9 C10 C11 -179.00(12) . . . 2_576 ? C10 C9 C11 C10 -0.1(2) . . . 2_576 ? C8 C9 C11 C10 179.01(12) . . . 2_576 ? C17 C12 C13 C14 -2.5(10) . . . . ? Cl1 C12 C13 C14 178.0(6) . . . . ? C17 C12 C13 Cl2 177.9(5) . . . . ? Cl1 C12 C13 Cl2 -1.6(9) . . . . ? C12 C13 C14 O1 -172.2(10) . . . . ? Cl2 C13 C14 O1 7.4(13) . . . . ? C12 C13 C14 C15 2.5(11) . . . . ? Cl2 C13 C14 C15 -177.8(7) . . . . ? O1 C14 C15 C16 172.9(10) . . . . ? C13 C14 C15 C16 -2.0(12) . . . . ? O1 C14 C15 C18 -7.0(13) . . . . ? C13 C14 C15 C18 178.1(7) . . . . ? C18 C15 C16 C19 3.0(10) . . . . ? C14 C15 C16 C19 -176.9(7) . . . . ? C18 C15 C16 C17 -178.7(6) . . . . ? C14 C15 C16 C17 1.4(10) . . . . ? C13 C12 C17 O2 -177.3(6) . . . . ? Cl1 C12 C17 O2 2.1(6) . . . . ? C13 C12 C17 C16 1.8(7) . . . . ? Cl1 C12 C17 C16 -178.7(4) . . . . ? C15 C16 C17 O2 177.9(6) . . . . ? C19 C16 C17 O2 -3.7(7) . . . . ? C15 C16 C17 C12 -1.2(8) . . . . ? C19 C16 C17 C12 177.2(4) . . . . ? C17B C12B C13B C14B 4.5(16) . . . . ? Cl1B C12B C13B C14B -177.5(10) . . . . ? C17B C12B C13B Cl2B -177.2(8) . . . . ? Cl1B C12B C13B Cl2B 0.7(15) . . . . ? C12B C13B C14B O1B -176.0(16) . . . . ? Cl2B C13B C14B O1B 6(2) . . . . ? C12B C13B C14B C15B -2.5(18) . . . . ? Cl2B C13B C14B C15B 179.1(11) . . . . ? O1B C14B C15B C16B 173.2(15) . . . . ? C13B C14B C15B C16B -0.6(18) . . . . ? O1B C14B C15B C18B -6.6(19) . . . . ? C13B C14B C15B C18B 179.6(11) . . . . ? C18B C15B C16B C19B 0.6(15) . . . . ? C14B C15B C16B C19B -179.2(10) . . . . ? C18B C15B C16B C17B -178.8(8) . . . . ? C14B C15B C16B C17B 1.5(15) . . . . ? C13B C12B C17B O2B 176.8(9) . . . . ? Cl1B C12B C17B O2B -1.2(10) . . . . ? C13B C12B C17B C16B -3.5(12) . . . . ? Cl1B C12B C17B C16B 178.4(5) . . . . ? C15B C16B C17B O2B -179.9(9) . . . . ? C19B C16B C17B O2B 0.7(9) . . . . ? C15B C16B C17B C12B 0.4(11) . . . . ? C19B C16B C17B C12B -178.9(6) . . . . ?