#------------------------------------------------------------------------------ #$Date: 2016-05-12 09:31:33 +0300 (Thu, 12 May 2016) $ #$Revision: 182904 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/22/52/7225217.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_7225217 loop_ _publ_author_name 'Cacciarini, Martina' 'Jevric, Martyn' 'Elm, Jonas' 'Petersen, Anne U.' 'Mikkelsen, Kurt V.' 'Nielsen, Mogens Brondsted' _publ_section_title ; Fine-tuning the lifetimes and energy storage capacities of meta-stable vinylheptafulvenes via substitution at the vinyl position ; _journal_name_full 'RSC Adv.' _journal_paper_doi 10.1039/C6RA06045E _journal_year 2016 _chemical_formula_moiety 'C24 H18 N2 O, C H2 Cl2' _chemical_formula_sum 'C25 H20 Cl2 N2 O' _chemical_formula_weight 435.33 _chemical_melting_point 193.5(15) _chemical_name_systematic '(1S,8aR or 1R,8aS)-1-cyano-2,3-diphenyl-1,8a-dihydroazulene-1-carboxamide' _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -1' _symmetry_cell_setting triclinic _symmetry_Int_Tables_number 2 _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _atom_sites_solution_hydrogens difmap _atom_sites_solution_primary direct _audit_creation_date 2015-08-18 _audit_creation_method ; Olex2 1.2 (compiled 2015.01.26 svn.r3151 for OlexSys, GUI svn.r4998) ; _audit_update_record ; 2016-02-19 deposited with the CCDC. 2016-05-10 downloaded from the CCDC. ; _cell_angle_alpha 92.611(8) _cell_angle_beta 107.490(8) _cell_angle_gamma 111.309(8) _cell_formula_units_Z 2 _cell_length_a 9.125(2) _cell_length_b 11.439(3) _cell_length_c 11.631(3) _cell_measurement_reflns_used 9815 _cell_measurement_temperature 122(2) _cell_measurement_theta_max 32.65 _cell_measurement_theta_min 2.45 _cell_volume 1062.3(5) _computing_cell_refinement 'SAINT v8.34A (Bruker, 2013)' _computing_data_reduction 'SAINT v8.34A (Bruker, 2013)' _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'XL (Sheldrick, 2008)' _computing_structure_solution 'XS (Sheldrick, 2008)' _diffrn_ambient_temperature 122 _diffrn_measured_fraction_theta_full 0.893 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0492 _diffrn_reflns_av_unetI/netI 0.0347 _diffrn_reflns_Laue_measured_fraction_full 0.893 _diffrn_reflns_Laue_measured_fraction_max 0.999 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_l_max 13 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_number 20771 _diffrn_reflns_point_group_measured_fraction_full 0.893 _diffrn_reflns_point_group_measured_fraction_max 0.999 _diffrn_reflns_theta_full 26.000 _diffrn_reflns_theta_max 25.027 _diffrn_reflns_theta_min 2.446 _diffrn_source 'sealed X-ray tube' _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.325 _exptl_absorpt_correction_T_max 0.7401 _exptl_absorpt_correction_T_min 0.6799 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2012/1 (Bruker,2012) was used for absorption correction. wR2(int) was 0.1235 before and 0.0810 after correction. The Ratio of minimum to maximum transmission is 0.9187. The \l/2 correction factor is 0.0015. ; _exptl_crystal_colour Yellow _exptl_crystal_density_diffrn 1.361 _exptl_crystal_description prism _exptl_crystal_F_000 452 _exptl_crystal_size_max 0.352 _exptl_crystal_size_mid 0.298 _exptl_crystal_size_min 0.160 _refine_diff_density_max 0.273 _refine_diff_density_min -0.314 _refine_diff_density_rms 0.047 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.049 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 351 _refine_ls_number_reflns 3739 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.049 _refine_ls_R_factor_all 0.0372 _refine_ls_R_factor_gt 0.0326 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0358P)^2^+0.5606P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0821 _refine_ls_wR_factor_ref 0.0852 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3368 _reflns_number_total 3739 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c6ra06045e2.cif _cod_data_source_block mo_d8v1290_0ma _cod_depositor_comments ; The following automatic conversions were performed: '_chemical_melting_point' value '192-195' was changed to '193.5(15)' - the average value was taken and precision was estimated. Automatic conversion script Id: cif_fix_values 4268 2015-11-12 08:31:59Z antanas ; _cod_original_cell_volume 1062.3(4) _cod_database_code 7225217 _shelxl_version_number 2014/6 _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. ; _olex2_refinement_description ; ; _shelx_res_file ; TITL mo_D8V1290_0ma in P-1 #2 REM reset to P-1 #2 CELL 0.71073 9.1254 11.4394 11.6306 92.6106 107.49 111.3092 ZERR 2 0.0021 0.0027 0.0025 0.0078 0.0077 0.008 LATT 1 SFAC C H N O Cl UNIT 48 32 4 2 1 L.S. 4 PLAN 20 TEMP 0 BOND MORE -1 BOND $H CONF fmap 2 acta 52 REM REM REM WGHT 0.035800 0.560600 FVAR 0.24495 O3 4 -0.166948 0.419655 0.365261 11.00000 0.02444 0.01332 = 0.02145 0.00328 0.00252 0.01046 N4 3 -0.049981 0.632634 0.427819 11.00000 0.01913 0.01279 = 0.01561 0.00395 0.00169 0.00669 N5 3 -0.389012 0.359269 0.058216 11.00000 0.02963 0.02224 = 0.02341 -0.00207 0.00690 0.01058 C6 1 -0.238251 0.674799 0.203288 11.00000 0.01302 0.01284 = 0.01090 0.00261 0.00177 0.00538 C7 1 -0.347086 0.438935 0.138894 11.00000 0.01649 0.01522 = 0.01800 0.00572 0.00600 0.00898 C8 1 -0.278079 0.881951 0.239400 11.00000 0.01823 0.01309 = 0.01538 0.00359 0.01070 0.00734 C9 1 -0.427336 0.671745 0.301529 11.00000 0.01263 0.01315 = 0.01438 0.00237 0.00253 0.00549 C10 1 -0.160509 0.526815 0.350412 11.00000 0.01372 0.01389 = 0.01381 0.00384 0.00761 0.00743 C11 1 0.003193 0.834085 0.000679 11.00000 0.02658 0.01855 = 0.01591 0.00603 0.00888 0.00765 C12 1 -0.736107 0.509110 0.358391 11.00000 0.01650 0.02662 = 0.02674 0.01185 0.01144 0.01009 C13 1 -0.310248 0.745781 0.243423 11.00000 0.01159 0.01343 = 0.01201 0.00192 0.00203 0.00533 C14 1 -0.123733 0.976910 0.307732 11.00000 0.02174 0.01781 = 0.02497 0.00198 0.01031 0.00698 C15 1 -0.617111 0.453622 0.208293 11.00000 0.01913 0.01625 = 0.02089 0.00126 0.00423 0.00546 C16 1 -0.631182 0.630958 0.409624 11.00000 0.02090 0.02653 = 0.02145 0.00610 0.01130 0.01302 C17 1 -0.745791 0.439743 0.247207 11.00000 0.01518 0.02037 = 0.02769 0.00410 0.00453 0.00304 C18 1 -0.006850 0.648424 0.146926 11.00000 0.01966 0.01915 = 0.01730 0.00682 0.00744 0.01075 C19 1 -0.507150 0.713315 0.363788 11.00000 0.01977 0.01535 = 0.02118 0.00364 0.00877 0.00875 C20 1 0.108827 0.681435 0.086683 11.00000 0.01804 0.02571 = 0.01973 0.00287 0.00756 0.01134 C21 1 -0.111977 0.802195 0.061696 11.00000 0.01971 0.01586 = 0.01581 0.00272 0.00596 0.00902 C22 1 0.114822 0.774735 0.014138 11.00000 0.01938 0.02578 = 0.01683 0.00275 0.01001 0.00637 C23 1 -0.406465 0.916676 0.172334 11.00000 0.02350 0.02033 = 0.02303 0.00823 0.01117 0.01234 C24 1 -0.441516 0.536204 0.289333 11.00000 0.01488 0.01181 = 0.01606 0.00370 0.00619 0.00595 C25 1 -0.227263 1.138123 0.244138 11.00000 0.05715 0.01412 = 0.03023 0.00874 0.03032 0.01719 C26 1 -0.117860 0.709633 0.137225 11.00000 0.01426 0.01316 = 0.01168 -0.00026 0.00341 0.00501 C27 1 -0.295091 0.543005 0.241131 11.00000 0.01497 0.01102 = 0.01336 0.00213 0.00478 0.00640 C29 1 -0.098663 1.104373 0.309579 11.00000 0.03675 0.01402 = 0.02930 -0.00235 0.01720 0.00127 C30 1 -0.380294 1.044359 0.174568 11.00000 0.04431 0.02763 = 0.02853 0.01548 0.02186 0.02681 CL1 5 -0.275198 1.065914 0.542967 11.00000 0.02257 0.03241 = 0.02602 0.00309 0.00750 0.00743 CL2 5 -0.323389 0.868382 0.697379 11.00000 0.04570 0.03564 = 0.04495 0.01277 0.01901 0.01799 C1 1 -0.305194 1.024792 0.681933 11.00000 0.03319 0.03356 = 0.02292 0.00188 0.00956 0.01426 H23 2 -0.512045 0.849779 0.123297 11.00000 0.02162 H24 2 -0.424698 0.507311 0.368701 11.00000 0.01321 H14 2 -0.034637 0.954385 0.355224 11.00000 0.02131 H11 2 0.004343 0.896197 -0.051037 11.00000 0.02173 H18 2 -0.007820 0.584207 0.196355 11.00000 0.01880 H19 2 -0.479535 0.804255 0.379866 11.00000 0.01858 H16 2 -0.643388 0.670366 0.478176 11.00000 0.02511 H4A 2 0.025064 0.626646 0.489964 11.00000 0.02721 H21 2 -0.193153 0.842590 0.050885 11.00000 0.02218 H22 2 0.194114 0.798287 -0.026742 11.00000 0.02670 H29 2 0.003862 1.167930 0.352838 11.00000 0.03239 H20 2 0.186894 0.639261 0.096786 11.00000 0.02583 H12 2 -0.821748 0.467025 0.392177 11.00000 0.02527 H1A 2 -0.405011 1.030970 0.683755 11.00000 0.03736 H17 2 -0.856971 0.377255 0.194861 11.00000 0.02778 H15 2 -0.635157 0.409786 0.129526 11.00000 0.03039 H30 2 -0.468368 1.068108 0.127007 11.00000 0.03426 H25 2 -0.209613 1.224538 0.247599 11.00000 0.03448 H4B 2 -0.043404 0.706115 0.410563 11.00000 0.02888 H1B 2 -0.206339 1.081386 0.748821 11.00000 0.06057 HKLF 4 REM mo_D8V1290_0ma in P-1 #2 REM R1 = 0.0326 for 3368 Fo > 4sig(Fo) and 0.0372 for all 3739 data REM 351 parameters refined using 0 restraints END WGHT 0.0358 0.5606 REM Highest difference peak 0.273, deepest hole -0.314, 1-sigma level 0.047 Q1 1 -0.4468 0.5995 0.2812 11.00000 0.05 0.27 Q2 1 -0.3577 0.7183 0.2795 11.00000 0.05 0.23 Q3 1 -0.1689 0.7008 0.1731 11.00000 0.05 0.22 Q4 1 -0.2586 0.6124 0.2176 11.00000 0.05 0.22 Q5 1 -0.2304 0.5361 0.2927 11.00000 0.05 0.21 Q6 1 -0.3699 0.5364 0.2540 11.00000 0.05 0.21 Q7 1 -0.5057 0.6870 0.2999 11.00000 0.05 0.20 Q8 1 -0.5204 0.4990 0.2453 11.00000 0.05 0.19 Q9 1 -0.2412 0.7227 0.2477 11.00000 0.05 0.19 Q10 1 -0.2169 0.9273 0.2733 11.00000 0.05 0.17 Q11 1 -0.5249 0.4325 0.3241 11.00000 0.05 0.17 Q12 1 -0.3171 0.5004 0.1952 11.00000 0.05 0.16 Q13 1 -0.1215 0.7472 0.0926 11.00000 0.05 0.16 Q14 1 -0.0438 0.7020 0.1603 11.00000 0.05 0.15 Q15 1 -0.1402 1.1558 0.5881 11.00000 0.05 0.15 Q16 1 -0.1233 1.0371 0.3287 11.00000 0.05 0.15 Q17 1 -0.4304 0.8538 0.6705 11.00000 0.05 0.15 Q18 1 -0.0459 0.8193 0.0367 11.00000 0.05 0.15 Q19 1 -0.4972 0.9138 0.4633 11.00000 0.05 0.15 Q20 1 -0.7191 0.4844 0.3164 11.00000 0.05 0.15 ; _shelx_res_checksum 97110 _olex2_submission_special_instructions 'No special instructions were received' 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 O3 O -0.16695(13) 0.41965(10) 0.36526(10) 0.0201(2) Uani 1 1 d N4 N -0.04998(16) 0.63263(13) 0.42782(13) 0.0167(3) Uani 1 1 d N5 N -0.38901(18) 0.35927(13) 0.05822(13) 0.0257(3) Uani 1 1 d C6 C -0.23825(17) 0.67480(13) 0.20329(13) 0.0127(3) Uani 1 1 d C7 C -0.34709(18) 0.43894(14) 0.13889(14) 0.0156(3) Uani 1 1 d C8 C -0.27808(18) 0.88195(13) 0.23940(14) 0.0140(3) Uani 1 1 d C9 C -0.42734(17) 0.67174(13) 0.30153(13) 0.0138(3) Uani 1 1 d C10 C -0.16051(17) 0.52681(13) 0.35041(13) 0.0125(3) Uani 1 1 d C11 C 0.0032(2) 0.83409(15) 0.00068(15) 0.0202(3) Uani 1 1 d C12 C -0.7361(2) 0.50911(16) 0.35839(16) 0.0216(3) Uani 1 1 d C13 C -0.31025(17) 0.74578(13) 0.24342(13) 0.0127(3) Uani 1 1 d C14 C -0.1237(2) 0.97691(15) 0.30773(16) 0.0213(3) Uani 1 1 d C15 C -0.61711(19) 0.45362(15) 0.20829(15) 0.0199(3) Uani 1 1 d C16 C -0.6312(2) 0.63096(16) 0.40962(15) 0.0208(3) Uani 1 1 d C17 C -0.7458(2) 0.43974(15) 0.24721(16) 0.0230(4) Uani 1 1 d C18 C -0.00685(19) 0.64842(15) 0.14693(14) 0.0174(3) Uani 1 1 d C19 C -0.50715(19) 0.71332(15) 0.36379(15) 0.0178(3) Uani 1 1 d C20 C 0.10883(19) 0.68144(15) 0.08668(15) 0.0201(3) Uani 1 1 d C21 C -0.11198(19) 0.80220(14) 0.06170(14) 0.0166(3) Uani 1 1 d C22 C 0.1148(2) 0.77473(15) 0.01414(15) 0.0205(3) Uani 1 1 d C23 C -0.4065(2) 0.91668(15) 0.17233(15) 0.0202(3) Uani 1 1 d C24 C -0.44152(18) 0.53620(13) 0.28933(14) 0.0138(3) Uani 1 1 d C25 C -0.2273(3) 1.13812(16) 0.24414(17) 0.0290(4) Uani 1 1 d C26 C -0.11786(18) 0.70963(13) 0.13723(13) 0.0135(3) Uani 1 1 d C27 C -0.29509(17) 0.54300(13) 0.24113(13) 0.0127(3) Uani 1 1 d C29 C -0.0987(2) 1.10437(16) 0.30958(17) 0.0281(4) Uani 1 1 d C30 C -0.3803(2) 1.04436(16) 0.17457(17) 0.0270(4) Uani 1 1 d Cl1 Cl -0.27520(5) 1.06591(4) 0.54297(4) 0.02830(13) Uani 1 1 d Cl2 Cl -0.32339(6) 0.86838(5) 0.69738(5) 0.04046(14) Uani 1 1 d C1 C -0.3052(3) 1.02479(18) 0.68193(17) 0.0297(4) Uani 1 1 d H23 H -0.512(2) 0.8498(17) 0.1233(17) 0.022(4) Uiso 1 1 d H24 H -0.425(2) 0.5073(15) 0.3687(16) 0.013(4) Uiso 1 1 d H14 H -0.035(2) 0.9544(17) 0.3552(17) 0.021(4) Uiso 1 1 d H11 H 0.004(2) 0.8962(17) -0.0510(17) 0.022(4) Uiso 1 1 d H18 H -0.008(2) 0.5842(17) 0.1964(17) 0.019(4) Uiso 1 1 d H19 H -0.480(2) 0.8043(17) 0.3799(16) 0.019(4) Uiso 1 1 d H16 H -0.643(2) 0.6704(17) 0.4782(18) 0.025(5) Uiso 1 1 d H4A H 0.025(3) 0.6266(18) 0.490(2) 0.027(5) Uiso 1 1 d H21 H -0.193(2) 0.8426(17) 0.0509(17) 0.022(4) Uiso 1 1 d H22 H 0.194(2) 0.7983(17) -0.0267(18) 0.027(5) Uiso 1 1 d H29 H 0.004(3) 1.168(2) 0.3528(19) 0.032(5) Uiso 1 1 d H20 H 0.187(2) 0.6393(17) 0.0968(18) 0.026(5) Uiso 1 1 d H12 H -0.822(2) 0.4670(17) 0.3922(17) 0.025(5) Uiso 1 1 d H1A H -0.405(3) 1.0310(19) 0.684(2) 0.037(5) Uiso 1 1 d H17 H -0.857(2) 0.3773(18) 0.1949(18) 0.028(5) Uiso 1 1 d H15 H -0.635(2) 0.4098(18) 0.1295(19) 0.030(5) Uiso 1 1 d H30 H -0.468(3) 1.0681(19) 0.127(2) 0.034(5) Uiso 1 1 d H25 H -0.210(2) 1.225(2) 0.2476(19) 0.034(5) Uiso 1 1 d H4B H -0.043(2) 0.706(2) 0.4106(19) 0.029(5) Uiso 1 1 d H1B H -0.206(3) 1.081(2) 0.749(3) 0.061(7) Uiso 1 1 d loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O3 0.0244(6) 0.0133(5) 0.0214(6) 0.0033(4) 0.0025(5) 0.0105(4) N4 0.0191(7) 0.0128(7) 0.0156(7) 0.0040(5) 0.0017(6) 0.0067(5) N5 0.0296(8) 0.0222(7) 0.0234(8) -0.0021(6) 0.0069(6) 0.0106(6) C6 0.0130(7) 0.0128(7) 0.0109(7) 0.0026(6) 0.0018(6) 0.0054(6) C7 0.0165(7) 0.0152(7) 0.0180(8) 0.0057(7) 0.0060(6) 0.0090(6) C8 0.0182(7) 0.0131(7) 0.0154(7) 0.0036(6) 0.0107(6) 0.0073(6) C9 0.0126(7) 0.0132(7) 0.0144(7) 0.0024(6) 0.0025(6) 0.0055(6) C10 0.0137(7) 0.0139(7) 0.0138(7) 0.0038(6) 0.0076(6) 0.0074(6) C11 0.0266(8) 0.0185(8) 0.0159(8) 0.0060(6) 0.0089(7) 0.0076(7) C12 0.0165(7) 0.0266(9) 0.0267(9) 0.0118(7) 0.0114(7) 0.0101(7) C13 0.0116(7) 0.0134(7) 0.0120(7) 0.0019(6) 0.0020(6) 0.0053(6) C14 0.0217(8) 0.0178(8) 0.0250(9) 0.0020(7) 0.0103(7) 0.0070(7) C15 0.0191(8) 0.0163(8) 0.0209(9) 0.0013(7) 0.0042(7) 0.0055(6) C16 0.0209(8) 0.0265(9) 0.0214(9) 0.0061(7) 0.0113(7) 0.0130(7) C17 0.0152(8) 0.0204(8) 0.0277(9) 0.0041(7) 0.0045(7) 0.0030(7) C18 0.0197(8) 0.0191(8) 0.0173(8) 0.0068(6) 0.0074(6) 0.0108(6) C19 0.0198(8) 0.0154(8) 0.0212(8) 0.0036(6) 0.0088(6) 0.0087(6) C20 0.0180(8) 0.0257(8) 0.0197(8) 0.0029(7) 0.0076(6) 0.0113(7) C21 0.0197(8) 0.0159(7) 0.0158(8) 0.0027(6) 0.0060(6) 0.0090(6) C22 0.0194(8) 0.0258(9) 0.0168(8) 0.0028(7) 0.0100(7) 0.0064(7) C23 0.0235(8) 0.0203(8) 0.0230(8) 0.0082(7) 0.0112(7) 0.0123(7) C24 0.0149(7) 0.0118(7) 0.0161(8) 0.0037(6) 0.0062(6) 0.0059(6) C25 0.0571(12) 0.0141(8) 0.0302(10) 0.0087(7) 0.0303(9) 0.0172(8) C26 0.0143(7) 0.0132(7) 0.0117(7) -0.0003(5) 0.0034(6) 0.0050(6) C27 0.0150(7) 0.0110(7) 0.0134(7) 0.0021(6) 0.0048(6) 0.0064(6) C29 0.0368(10) 0.0140(8) 0.0293(10) -0.0023(7) 0.0172(8) 0.0013(8) C30 0.0443(11) 0.0276(9) 0.0285(9) 0.0155(8) 0.0219(8) 0.0268(9) Cl1 0.0226(2) 0.0324(2) 0.0260(2) 0.00309(17) 0.00750(17) 0.00743(17) Cl2 0.0457(3) 0.0356(3) 0.0450(3) 0.0128(2) 0.0190(2) 0.0180(2) C1 0.0332(10) 0.0336(10) 0.0229(9) 0.0019(8) 0.0096(8) 0.0143(8) 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' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle C10 N4 H4A 118.3(13) C10 N4 H4B 120.9(14) H4A N4 H4B 120.1(19) C13 C6 C26 129.41(13) C13 C6 C27 109.85(12) C26 C6 C27 120.70(12) N5 C7 C27 178.75(17) C14 C8 C13 120.66(14) C14 C8 C23 119.09(14) C23 C8 C13 120.13(13) C13 C9 C24 109.53(12) C19 C9 C13 128.13(14) C19 C9 C24 122.24(13) O3 C10 N4 123.86(14) O3 C10 C27 119.85(12) N4 C10 C27 116.12(12) C21 C11 C22 120.37(15) C21 C11 H11 119.4(11) C22 C11 H11 120.2(11) C16 C12 C17 125.95(15) C16 C12 H12 117.8(11) C17 C12 H12 115.8(11) C6 C13 C8 128.49(13) C6 C13 C9 111.19(13) C9 C13 C8 120.26(12) C8 C14 H14 120.0(11) C29 C14 C8 120.12(16) C29 C14 H14 119.9(11) C17 C15 C24 119.98(15) C17 C15 H15 120.9(11) C24 C15 H15 119.1(11) C12 C16 C19 125.63(15) C12 C16 H16 119.0(11) C19 C16 H16 115.2(11) C12 C17 H17 117.3(11) C15 C17 C12 125.81(15) C15 C17 H17 116.9(11) C20 C18 C26 121.07(15) C20 C18 H18 118.2(10) C26 C18 H18 120.8(10) C9 C19 C16 124.07(14) C9 C19 H19 118.5(10) C16 C19 H19 117.4(10) C18 C20 H20 119.5(11) C22 C20 C18 120.03(15) C22 C20 H20 120.4(11) C11 C21 C26 120.57(14) C11 C21 H21 120.6(10) C26 C21 H21 118.8(10) C11 C22 H22 119.7(11) C20 C22 C11 119.84(14) C20 C22 H22 120.5(11) C8 C23 H23 118.2(11) C30 C23 C8 120.43(16) C30 C23 H23 121.3(11) C9 C24 C27 103.13(11) C9 C24 H24 111.4(9) C15 C24 C9 107.52(12) C15 C24 C27 117.51(13) C15 C24 H24 106.9(9) C27 C24 H24 110.4(9) C29 C25 H25 119.7(13) C30 C25 C29 119.76(15) C30 C25 H25 120.5(13) C18 C26 C6 120.39(13) C21 C26 C6 121.51(13) C21 C26 C18 118.09(13) C6 C27 C10 113.89(11) C6 C27 C24 104.69(11) C7 C27 C6 112.07(12) C7 C27 C10 107.68(11) C7 C27 C24 112.84(12) C10 C27 C24 105.58(11) C14 C29 H29 120.8(13) C25 C29 C14 120.49(17) C25 C29 H29 118.7(13) C23 C30 H30 120.3(12) C25 C30 C23 120.11(17) C25 C30 H30 119.6(12) Cl1 C1 H1A 108.8(13) Cl1 C1 H1B 107.5(15) Cl2 C1 Cl1 112.65(10) Cl2 C1 H1A 107.8(13) Cl2 C1 H1B 106.8(15) H1A C1 H1B 113.3(19) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance O3 C10 1.2284(18) N4 C10 1.327(2) N4 H4A 0.86(2) N4 H4B 0.86(2) N5 C7 1.145(2) C6 C13 1.359(2) C6 C26 1.474(2) C6 C27 1.5379(19) C7 C27 1.476(2) C8 C13 1.482(2) C8 C14 1.390(2) C8 C23 1.399(2) C9 C13 1.464(2) C9 C19 1.348(2) C9 C24 1.505(2) C10 C27 1.551(2) C11 C21 1.391(2) C11 C22 1.393(2) C11 H11 0.951(19) C12 C16 1.351(2) C12 C17 1.448(2) C12 H12 0.962(19) C14 C29 1.389(2) C14 H14 0.963(19) C15 C17 1.341(2) C15 C24 1.503(2) C15 H15 0.96(2) C16 C19 1.444(2) C16 H16 0.95(2) C17 H17 0.99(2) C18 C20 1.388(2) C18 C26 1.408(2) C18 H18 0.952(19) C19 H19 0.972(18) C20 C22 1.386(2) C20 H20 0.979(19) C21 C26 1.403(2) C21 H21 0.988(18) C22 H22 0.948(19) C23 C30 1.389(2) C23 H23 0.966(19) C24 C27 1.5762(19) C24 H24 0.982(18) C25 C29 1.387(3) C25 C30 1.381(3) C25 H25 0.94(2) C29 H29 0.92(2) C30 H30 0.96(2) Cl1 C1 1.7748(19) Cl2 C1 1.759(2) C1 H1A 0.95(2) C1 H1B 0.97(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 O3 C10 C27 C6 -157.26(13) O3 C10 C27 C7 -32.33(17) O3 C10 C27 C24 88.45(15) N4 C10 C27 C6 27.15(17) N4 C10 C27 C7 152.08(13) N4 C10 C27 C24 -87.14(14) C8 C14 C29 C25 0.4(2) C8 C23 C30 C25 -0.6(2) C9 C24 C27 C6 -12.44(14) C9 C24 C27 C7 -134.58(13) C9 C24 C27 C10 108.07(12) C11 C21 C26 C6 179.67(14) C11 C21 C26 C18 -1.4(2) C12 C16 C19 C9 -30.4(3) C13 C6 C26 C18 153.57(15) C13 C6 C26 C21 -27.6(2) C13 C6 C27 C7 133.24(13) C13 C6 C27 C10 -104.21(14) C13 C6 C27 C24 10.60(15) C13 C8 C14 C29 -175.72(14) C13 C8 C23 C30 175.81(14) C13 C9 C19 C16 174.79(15) C13 C9 C24 C15 -114.15(14) C13 C9 C24 C27 10.67(15) C14 C8 C13 C6 -65.8(2) C14 C8 C13 C9 111.05(16) C14 C8 C23 C30 -0.4(2) C15 C24 C27 C6 105.59(14) C15 C24 C27 C7 -16.54(18) C15 C24 C27 C10 -133.90(13) C16 C12 C17 C15 33.4(3) C17 C12 C16 C19 -1.3(3) C17 C15 C24 C9 -67.42(19) C17 C15 C24 C27 176.93(14) C18 C20 C22 C11 -0.8(2) C19 C9 C13 C6 171.89(15) C19 C9 C13 C8 -5.5(2) C19 C9 C24 C15 69.16(18) C19 C9 C24 C27 -166.02(14) C20 C18 C26 C6 -179.07(14) C20 C18 C26 C21 2.0(2) C21 C11 C22 C20 1.4(2) C22 C11 C21 C26 -0.2(2) C23 C8 C13 C6 118.09(17) C23 C8 C13 C9 -65.06(19) C23 C8 C14 C29 0.4(2) C24 C9 C13 C6 -4.56(17) C24 C9 C13 C8 178.08(13) C24 C9 C19 C16 -9.2(2) C24 C15 C17 C12 7.3(3) C26 C6 C13 C8 -4.8(3) C26 C6 C13 C9 178.13(14) C26 C6 C27 C7 -48.77(17) C26 C6 C27 C10 73.78(16) C26 C6 C27 C24 -171.41(13) C26 C18 C20 C22 -0.9(2) C27 C6 C13 C8 172.98(14) C27 C6 C13 C9 -4.11(17) C27 C6 C26 C18 -24.0(2) C27 C6 C26 C21 154.89(14) C29 C25 C30 C23 1.4(2) C30 C25 C29 C14 -1.4(2)