#------------------------------------------------------------------------------ #$Date: 2021-05-21 06:13:37 +0300 (Fri, 21 May 2021) $ #$Revision: 265400 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/06/06/7060684.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_7060684 loop_ _publ_author_name 'Ge, Yuxi' 'Huang, Bin' _publ_section_title ; Light-emitting analogues based on triphenylamine modified quinoxaline and pyridine[2,3-b]pyrazine exhibiting different mechanochromic luminescence ; _journal_name_full 'New Journal of Chemistry' _journal_paper_doi 10.1039/D1NJ01350E _journal_year 2021 _chemical_formula_moiety 'C38 H27 N3' _chemical_formula_sum 'C38 H27 N3' _chemical_formula_weight 525.62 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2ybc' _space_group_name_H-M_alt 'P 1 21/c 1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary dual _audit_creation_date 2020-05-19 _audit_creation_method ; Olex2 1.3 (compiled Nov 21 2019 18:26:39 for OlexSys, GUI svn.r6003) ; _audit_update_record ; 2021-02-25 deposited with the CCDC. 2021-05-19 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 116.868(2) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 19.2398(13) _cell_length_b 8.8918(6) _cell_length_c 18.0426(9) _cell_measurement_reflns_used 4081 _cell_measurement_temperature 150.0 _cell_measurement_theta_max 24.96 _cell_measurement_theta_min 2.37 _cell_volume 2753.5(3) _computing_cell_refinement 'SAINT v8.37A (Bruker, 2015)' _computing_data_reduction 'SAINT v8.37A (Bruker, 2015)' _computing_molecular_graphics 'Olex2 1.3 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.3 (Dolomanov et al., 2009)' _computing_structure_refinement 'SHELXL 2018/3 (Sheldrick, 2015)' _computing_structure_solution 'SHELXT 2018/2 (Sheldrick, 2018)' _diffrn_ambient_temperature 150.0 _diffrn_measured_fraction_theta_full 0.999 _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 0.1305 _diffrn_reflns_av_unetI/netI 0.0598 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.999 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 22 _diffrn_reflns_limit_l_min -22 _diffrn_reflns_number 48095 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.999 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 26.378 _diffrn_reflns_theta_min 2.258 _diffrn_source_current 30.0 _diffrn_source_power 1.5 _diffrn_source_voltage 50.0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.074 _exptl_absorpt_correction_T_max 0.7454 _exptl_absorpt_correction_T_min 0.6418 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.0760 before and 0.0702 after correction. The Ratio of minimum to maximum transmission is 0.8610. The \l/2 correction factor is Not present. ; _exptl_crystal_colour yellow _exptl_crystal_colour_primary yellow _exptl_crystal_density_diffrn 1.268 _exptl_crystal_description block _exptl_crystal_F_000 1104 _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.1 _refine_diff_density_max 0.187 _refine_diff_density_min -0.219 _refine_diff_density_rms 0.049 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.027 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 370 _refine_ls_number_reflns 5629 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.027 _refine_ls_R_factor_all 0.0971 _refine_ls_R_factor_gt 0.0492 _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^)+(0.0544P)^2^+0.5284P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1037 _refine_ls_wR_factor_ref 0.1278 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3551 _reflns_number_total 5629 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d1nj01350e2.cif _cod_data_source_block mo_0519_1_0ma _cod_database_code 7060684 _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_max 0.993 _shelx_estimated_absorpt_t_min 0.985 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups 2.a Aromatic/amide H refined with riding coordinates: C009(H009), C00B(H00B), C00C(H00C), C00D(H00D), C00G(H00G), C00H(H00H), C00I(H00I), C00K(H00K), C00L(H00L), C00N(H00N), C00O(H00O), C00P(H00P), C00Q(H00Q), C00R(H00R), C00S(H00S), C00T(H00T), C00U(H00U), C00V(H00V), C00W(H00W), C00X(H00X), C00Z(H00Z), C010(H010), C011(H011), C012(H012), C013(H013), C014(H014), C015(H015) ; _shelx_res_file ; TITL mo_0519_1_0ma_a.res in P2(1)/c mo_0519_1_0ma.res created by SHELXL-2018/3 at 09:51:57 on 19-May-2020 REM Old TITL mo_0519_1_0ma in P2(1)/c REM SHELXT solution in P2(1)/c: R1 0.156, Rweak 0.007, Alpha 0.036 REM 0.305 for 382 systematic absences, Orientation as input REM Formula found by SHELXT: C38 N3 CELL 0.71073 19.2398 8.8918 18.0426 90 116.868 90 ZERR 4 0.0013 0.0006 0.0009 0 0.002 0 LATT 1 SYMM -X,0.5+Y,0.5-Z SFAC C H N UNIT 152 108 12 L.S. 9 PLAN 2 SIZE 0.2 0.15 0.1 TEMP -123.15 CONF BOND list 4 fmap 2 53 MORE -1 ACTA BOND $H REM REM REM WGHT 0.054400 0.528400 FVAR 0.52006 N001 3 0.667570 0.331034 0.537215 11.00000 0.02389 0.02550 = 0.02367 -0.00014 0.01150 -0.00150 N002 3 0.732640 0.337402 0.711644 11.00000 0.02239 0.02896 = 0.02303 -0.00030 0.01110 0.00030 N003 3 0.291532 0.318266 0.768030 11.00000 0.02363 0.04565 = 0.02543 0.00177 0.01391 -0.00002 C004 1 0.861837 0.309509 0.727619 11.00000 0.02153 0.02644 = 0.02014 0.00320 0.01116 -0.00001 C005 1 0.743557 0.329250 0.583825 11.00000 0.02465 0.01900 = 0.02195 -0.00038 0.01078 -0.00157 C006 1 0.776825 0.326611 0.673166 11.00000 0.02321 0.02213 = 0.02263 0.00024 0.01143 -0.00070 C007 1 0.621420 0.334145 0.576495 11.00000 0.02228 0.02422 = 0.02223 0.00085 0.01050 -0.00019 C008 1 0.467752 0.355145 0.689973 11.00000 0.02163 0.02708 = 0.02578 0.00013 0.01176 -0.00113 C009 1 0.851425 0.437853 0.558161 11.00000 0.02573 0.02494 = 0.02533 0.00155 0.01233 0.00169 AFIX 43 H009 2 0.866578 0.499322 0.606046 11.00000 -1.20000 AFIX 0 C00A 1 0.790822 0.335681 0.537509 11.00000 0.02360 0.02482 = 0.02135 0.00279 0.01111 0.00277 C00B 1 0.889992 0.450909 0.509501 11.00000 0.02502 0.02934 = 0.03352 0.00682 0.01429 0.00242 AFIX 43 H00B 2 0.930654 0.522492 0.523462 11.00000 -1.20000 AFIX 0 C00C 1 0.603318 0.350494 0.701641 11.00000 0.02419 0.03263 = 0.02263 0.00068 0.01203 0.00004 AFIX 43 H00C 2 0.624834 0.355826 0.760451 11.00000 -1.20000 AFIX 0 C00D 1 0.898709 0.403403 0.796079 11.00000 0.02273 0.02906 = 0.02473 0.00034 0.01233 0.00274 AFIX 43 H00D 2 0.869675 0.479622 0.806554 11.00000 -1.20000 AFIX 0 C00E 1 0.653603 0.342357 0.663998 11.00000 0.02177 0.02498 = 0.02202 0.00242 0.00901 0.00092 C00F 1 0.216242 0.283388 0.704541 11.00000 0.02332 0.03449 = 0.02878 0.00739 0.01446 0.00102 C00G 1 0.397952 0.434574 0.650042 11.00000 0.02575 0.02637 = 0.02583 0.00342 0.01274 -0.00155 AFIX 43 H00G 2 0.388978 0.494401 0.602937 11.00000 -1.20000 AFIX 0 C00H 1 0.770003 0.245193 0.467220 11.00000 0.02755 0.02988 = 0.02571 -0.00287 0.01273 -0.00336 AFIX 43 H00H 2 0.728236 0.175790 0.451987 11.00000 -1.20000 AFIX 0 C00I 1 0.341472 0.428165 0.677523 11.00000 0.02335 0.02909 = 0.03015 0.00264 0.01176 0.00398 AFIX 43 H00I 2 0.294962 0.485254 0.650272 11.00000 -1.20000 AFIX 0 C00J 1 0.523917 0.350818 0.654614 11.00000 0.02430 0.02189 = 0.02933 0.00303 0.01372 0.00145 C00K 1 0.493050 0.340868 0.566478 11.00000 0.02213 0.03252 = 0.02551 0.00163 0.00824 -0.00041 AFIX 43 H00K 2 0.438167 0.340276 0.533190 11.00000 -1.20000 AFIX 0 C00L 1 0.480233 0.271690 0.760626 11.00000 0.02367 0.03542 = 0.02818 0.00752 0.01216 0.00691 AFIX 43 H00L 2 0.528521 0.221406 0.790849 11.00000 -1.20000 AFIX 0 C00M 1 0.352971 0.337739 0.745295 11.00000 0.02403 0.03200 = 0.02564 -0.00069 0.01363 -0.00090 C00N 1 0.208081 0.192083 0.638430 11.00000 0.02617 0.03301 = 0.03165 0.00604 0.01606 0.00179 AFIX 43 H00N 2 0.252973 0.149855 0.637355 11.00000 -1.20000 AFIX 0 C00O 1 0.423093 0.261383 0.787122 11.00000 0.03008 0.03547 = 0.02674 0.00799 0.01532 0.00338 AFIX 43 H00O 2 0.431934 0.201674 0.834229 11.00000 -1.20000 AFIX 0 C00P 1 0.905587 0.197185 0.714094 11.00000 0.03056 0.02917 = 0.02513 0.00008 0.01105 0.00523 AFIX 43 H00P 2 0.881350 0.131906 0.667688 11.00000 -1.20000 AFIX 0 C00Q 1 0.266197 0.251987 0.885246 11.00000 0.03173 0.03286 = 0.03284 0.00320 0.01682 -0.00032 AFIX 43 H00Q 2 0.230406 0.176919 0.852357 11.00000 -1.20000 AFIX 0 C00R 1 0.540338 0.332231 0.529137 11.00000 0.02601 0.03579 = 0.02226 0.00013 0.00918 -0.00109 AFIX 43 H00R 2 0.518221 0.324822 0.470349 11.00000 -1.20000 AFIX 0 C00S 1 0.977316 0.386871 0.849112 11.00000 0.02593 0.03289 = 0.02551 0.00088 0.00953 0.00034 AFIX 43 H00S 2 1.002049 0.452526 0.895264 11.00000 -1.20000 AFIX 0 C00T 1 0.359686 0.444861 0.901874 11.00000 0.03864 0.02616 = 0.03661 0.00307 0.02233 0.00205 AFIX 43 H00T 2 0.387450 0.503785 0.880159 11.00000 -1.20000 AFIX 0 C00U 1 0.809446 0.255563 0.419719 11.00000 0.03674 0.03711 = 0.02517 -0.00079 0.01705 0.00461 AFIX 43 H00U 2 0.795721 0.191739 0.372948 11.00000 -1.20000 AFIX 0 C00V 1 0.983949 0.180303 0.767778 11.00000 0.03113 0.03751 = 0.03282 0.00499 0.01503 0.01357 AFIX 43 H00V 2 1.013112 0.103123 0.758252 11.00000 -1.20000 AFIX 0 C00W 1 0.869170 0.359437 0.440478 11.00000 0.03191 0.03757 = 0.02924 0.00861 0.01961 0.00827 AFIX 43 H00W 2 0.895824 0.367892 0.407365 11.00000 -1.20000 AFIX 0 C00X 1 0.134889 0.162343 0.574139 11.00000 0.03544 0.03849 = 0.02864 0.00711 0.01342 -0.00307 AFIX 43 H00X 2 0.130009 0.101358 0.528804 11.00000 -1.20000 AFIX 0 C00Y 1 0.305893 0.338332 0.851697 11.00000 0.02920 0.02719 = 0.02877 0.00351 0.01589 0.00636 C00Z 1 1.019952 0.275021 0.835091 11.00000 0.02308 0.04120 = 0.02884 0.00590 0.00835 0.00617 AFIX 43 H00Z 2 1.073834 0.263464 0.871682 11.00000 -1.20000 AFIX 0 C010 1 0.372818 0.465154 0.983099 11.00000 0.04496 0.02821 = 0.03611 -0.00242 0.01978 -0.00013 AFIX 43 H010 2 0.410307 0.536821 1.017077 11.00000 -1.20000 AFIX 0 C011 1 0.149602 0.341845 0.705874 11.00000 0.02977 0.04087 = 0.03193 0.00585 0.01740 0.00454 AFIX 43 H011 2 0.154179 0.404159 0.750627 11.00000 -1.20000 AFIX 0 C012 1 0.278940 0.275657 0.966285 11.00000 0.03747 0.04048 = 0.03502 0.00766 0.02333 0.00538 AFIX 43 H012 2 0.250950 0.218057 0.988259 11.00000 -1.20000 AFIX 0 C013 1 0.076694 0.309159 0.641994 11.00000 0.02733 0.04753 = 0.04157 0.01752 0.01879 0.00858 AFIX 43 H013 2 0.031488 0.347874 0.643854 11.00000 -1.20000 AFIX 0 C014 1 0.068878 0.220984 0.575613 11.00000 0.02675 0.04553 = 0.03333 0.01321 0.00935 -0.00094 AFIX 43 H014 2 0.018746 0.200821 0.531465 11.00000 -1.20000 AFIX 0 C015 1 0.332089 0.382481 1.015560 11.00000 0.04606 0.03680 = 0.02998 0.00099 0.02292 0.00698 AFIX 43 H015 2 0.340483 0.398799 1.071024 11.00000 -1.20000 AFIX 0 HKLF 4 REM mo_0519_1_0ma_a.res in P2(1)/c REM wR2 = 0.1278, GooF = S = 1.027, Restrained GooF = 1.027 for all data REM R1 = 0.0492 for 3551 Fo > 4sig(Fo) and 0.0971 for all 5629 data REM 370 parameters refined using 0 restraints END WGHT 0.0529 0.5524 REM Highest difference peak 0.187, deepest hole -0.219, 1-sigma level 0.049 Q1 1 -0.0603 0.2123 0.5626 11.00000 0.05 0.19 Q2 1 0.3623 0.3813 0.5760 11.00000 0.05 0.18 ; _shelx_res_checksum 15641 _olex2_submission_special_instructions 'No special instructions were received' 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' 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 N001 N 0.66757(10) 0.33103(19) 0.53722(9) 0.0241(4) Uani 1 1 d . . . . . N002 N 0.73264(10) 0.33740(19) 0.71164(9) 0.0245(4) Uani 1 1 d . . . . . N003 N 0.29153(10) 0.3183(2) 0.76803(10) 0.0305(4) Uani 1 1 d . . . . . C004 C 0.86184(11) 0.3095(2) 0.72762(11) 0.0220(4) Uani 1 1 d . . . . . C005 C 0.74356(12) 0.3293(2) 0.58383(11) 0.0218(4) Uani 1 1 d . . . . . C006 C 0.77683(12) 0.3266(2) 0.67317(11) 0.0222(4) Uani 1 1 d . . . . . C007 C 0.62142(12) 0.3341(2) 0.57649(11) 0.0227(4) Uani 1 1 d . . . . . C008 C 0.46775(12) 0.3551(2) 0.68997(12) 0.0244(4) Uani 1 1 d . . . . . C009 C 0.85143(12) 0.4379(2) 0.55816(12) 0.0250(5) Uani 1 1 d . . . . . H009 H 0.866578 0.499322 0.606046 0.030 Uiso 1 1 calc R U . . . C00A C 0.79082(12) 0.3357(2) 0.53751(11) 0.0229(4) Uani 1 1 d . . . . . C00B C 0.88999(12) 0.4509(2) 0.50950(12) 0.0289(5) Uani 1 1 d . . . . . H00B H 0.930654 0.522492 0.523462 0.035 Uiso 1 1 calc R U . . . C00C C 0.60332(12) 0.3505(2) 0.70164(12) 0.0259(5) Uani 1 1 d . . . . . H00C H 0.624834 0.355826 0.760451 0.031 Uiso 1 1 calc R U . . . C00D C 0.89871(12) 0.4034(2) 0.79608(11) 0.0249(5) Uani 1 1 d . . . . . H00D H 0.869675 0.479622 0.806554 0.030 Uiso 1 1 calc R U . . . C00E C 0.65360(12) 0.3424(2) 0.66400(11) 0.0233(4) Uani 1 1 d . . . . . C00F C 0.21624(12) 0.2834(2) 0.70454(12) 0.0278(5) Uani 1 1 d . . . . . C00G C 0.39795(12) 0.4346(2) 0.65004(12) 0.0256(5) Uani 1 1 d . . . . . H00G H 0.388978 0.494401 0.602937 0.031 Uiso 1 1 calc R U . . . C00H C 0.77000(12) 0.2452(2) 0.46722(12) 0.0275(5) Uani 1 1 d . . . . . H00H H 0.728236 0.175790 0.451987 0.033 Uiso 1 1 calc R U . . . C00I C 0.34147(12) 0.4282(2) 0.67752(12) 0.0277(5) Uani 1 1 d . . . . . H00I H 0.294962 0.485254 0.650272 0.033 Uiso 1 1 calc R U . . . C00J C 0.52392(12) 0.3508(2) 0.65461(12) 0.0246(4) Uani 1 1 d . . . . . C00K C 0.49305(12) 0.3409(2) 0.56648(12) 0.0277(5) Uani 1 1 d . . . . . H00K H 0.438167 0.340276 0.533190 0.033 Uiso 1 1 calc R U . . . C00L C 0.48023(12) 0.2717(3) 0.76063(12) 0.0289(5) Uani 1 1 d . . . . . H00L H 0.528521 0.221406 0.790849 0.035 Uiso 1 1 calc R U . . . C00M C 0.35297(12) 0.3377(2) 0.74529(12) 0.0263(5) Uani 1 1 d . . . . . C00N C 0.20808(13) 0.1921(2) 0.63843(12) 0.0291(5) Uani 1 1 d . . . . . H00N H 0.252973 0.149855 0.637355 0.035 Uiso 1 1 calc R U . . . C00O C 0.42309(12) 0.2614(3) 0.78712(12) 0.0298(5) Uani 1 1 d . . . . . H00O H 0.431934 0.201674 0.834229 0.036 Uiso 1 1 calc R U . . . C00P C 0.90559(12) 0.1972(2) 0.71409(12) 0.0289(5) Uani 1 1 d . . . . . H00P H 0.881350 0.131906 0.667688 0.035 Uiso 1 1 calc R U . . . C00Q C 0.26620(13) 0.2520(3) 0.88525(13) 0.0316(5) Uani 1 1 d . . . . . H00Q H 0.230406 0.176919 0.852357 0.038 Uiso 1 1 calc R U . . . C00R C 0.54034(12) 0.3322(2) 0.52914(12) 0.0287(5) Uani 1 1 d . . . . . H00R H 0.518221 0.324822 0.470349 0.034 Uiso 1 1 calc R U . . . C00S C 0.97732(12) 0.3869(2) 0.84911(12) 0.0289(5) Uani 1 1 d . . . . . H00S H 1.002049 0.452526 0.895264 0.035 Uiso 1 1 calc R U . . . C00T C 0.35969(13) 0.4449(2) 0.90187(13) 0.0318(5) Uani 1 1 d . . . . . H00T H 0.387450 0.503785 0.880159 0.038 Uiso 1 1 calc R U . . . C00U C 0.80945(13) 0.2556(3) 0.41972(12) 0.0318(5) Uani 1 1 d . . . . . H00U H 0.795721 0.191739 0.372948 0.038 Uiso 1 1 calc R U . . . C00V C 0.98395(13) 0.1803(3) 0.76778(13) 0.0336(5) Uani 1 1 d . . . . . H00V H 1.013112 0.103123 0.758252 0.040 Uiso 1 1 calc R U . . . C00W C 0.86917(13) 0.3594(2) 0.44048(13) 0.0307(5) Uani 1 1 d . . . . . H00W H 0.895824 0.367892 0.407365 0.037 Uiso 1 1 calc R U . . . C00X C 0.13489(13) 0.1623(3) 0.57414(13) 0.0346(5) Uani 1 1 d . . . . . H00X H 0.130009 0.101358 0.528804 0.042 Uiso 1 1 calc R U . . . C00Y C 0.30589(12) 0.3383(2) 0.85170(12) 0.0273(5) Uani 1 1 d . . . . . C00Z C 1.01995(13) 0.2750(3) 0.83509(13) 0.0323(5) Uani 1 1 d . . . . . H00Z H 1.073834 0.263464 0.871682 0.039 Uiso 1 1 calc R U . . . C010 C 0.37282(14) 0.4652(3) 0.98310(13) 0.0359(5) Uani 1 1 d . . . . . H010 H 0.410307 0.536821 1.017077 0.043 Uiso 1 1 calc R U . . . C011 C 0.14960(13) 0.3418(3) 0.70587(13) 0.0329(5) Uani 1 1 d . . . . . H011 H 0.154179 0.404159 0.750627 0.039 Uiso 1 1 calc R U . . . C012 C 0.27894(13) 0.2757(3) 0.96628(13) 0.0350(5) Uani 1 1 d . . . . . H012 H 0.250950 0.218057 0.988259 0.042 Uiso 1 1 calc R U . . . C013 C 0.07669(13) 0.3092(3) 0.64199(14) 0.0376(6) Uani 1 1 d . . . . . H013 H 0.031488 0.347874 0.643854 0.045 Uiso 1 1 calc R U . . . C014 C 0.06888(14) 0.2210(3) 0.57561(14) 0.0368(6) Uani 1 1 d . . . . . H014 H 0.018746 0.200821 0.531465 0.044 Uiso 1 1 calc R U . . . C015 C 0.33209(14) 0.3825(3) 1.01556(14) 0.0354(6) Uani 1 1 d . . . . . H015 H 0.340483 0.398799 1.071024 0.043 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 N001 0.0239(10) 0.0255(9) 0.0237(8) -0.0001(7) 0.0115(7) -0.0015(7) N002 0.0224(9) 0.0290(10) 0.0230(8) -0.0003(7) 0.0111(7) 0.0003(8) N003 0.0236(10) 0.0457(12) 0.0254(9) 0.0018(8) 0.0139(8) 0.0000(8) C004 0.0215(11) 0.0264(11) 0.0201(9) 0.0032(8) 0.0112(8) 0.0000(8) C005 0.0247(11) 0.0190(10) 0.0219(9) -0.0004(8) 0.0108(9) -0.0016(8) C006 0.0232(11) 0.0221(11) 0.0226(9) 0.0002(8) 0.0114(9) -0.0007(8) C007 0.0223(11) 0.0242(11) 0.0222(9) 0.0009(8) 0.0105(8) -0.0002(9) C008 0.0216(11) 0.0271(11) 0.0258(10) 0.0001(8) 0.0118(9) -0.0011(9) C009 0.0257(12) 0.0249(11) 0.0253(10) 0.0016(8) 0.0123(9) 0.0017(9) C00A 0.0236(11) 0.0248(11) 0.0214(9) 0.0028(8) 0.0111(9) 0.0028(9) C00B 0.0250(12) 0.0293(12) 0.0335(11) 0.0068(9) 0.0143(10) 0.0024(9) C00C 0.0242(12) 0.0326(12) 0.0226(10) 0.0007(9) 0.0120(9) 0.0000(9) C00D 0.0227(11) 0.0291(12) 0.0247(10) 0.0003(8) 0.0123(9) 0.0027(9) C00E 0.0218(11) 0.0250(11) 0.0220(9) 0.0024(8) 0.0090(8) 0.0009(9) C00F 0.0233(11) 0.0345(12) 0.0288(11) 0.0074(9) 0.0145(9) 0.0010(9) C00G 0.0257(12) 0.0264(11) 0.0258(10) 0.0034(9) 0.0127(9) -0.0015(9) C00H 0.0276(12) 0.0299(12) 0.0257(10) -0.0029(9) 0.0127(9) -0.0034(9) C00I 0.0233(12) 0.0291(12) 0.0301(11) 0.0026(9) 0.0118(9) 0.0040(9) C00J 0.0243(11) 0.0219(11) 0.0293(10) 0.0030(8) 0.0137(9) 0.0015(9) C00K 0.0221(11) 0.0325(12) 0.0255(10) 0.0016(9) 0.0082(9) -0.0004(9) C00L 0.0237(11) 0.0354(13) 0.0282(11) 0.0075(9) 0.0122(9) 0.0069(10) C00M 0.0240(11) 0.0320(12) 0.0256(10) -0.0007(9) 0.0136(9) -0.0009(9) C00N 0.0262(12) 0.0330(13) 0.0316(11) 0.0060(9) 0.0161(10) 0.0018(10) C00O 0.0301(12) 0.0355(13) 0.0267(10) 0.0080(9) 0.0153(9) 0.0034(10) C00P 0.0306(13) 0.0292(12) 0.0251(10) 0.0001(9) 0.0111(9) 0.0052(9) C00Q 0.0317(13) 0.0329(13) 0.0328(11) 0.0032(10) 0.0168(10) -0.0003(10) C00R 0.0260(12) 0.0358(13) 0.0223(10) 0.0001(9) 0.0092(9) -0.0011(10) C00S 0.0259(12) 0.0329(12) 0.0255(10) 0.0009(9) 0.0095(9) 0.0003(9) C00T 0.0386(14) 0.0262(12) 0.0366(12) 0.0031(9) 0.0223(11) 0.0020(10) C00U 0.0367(13) 0.0371(13) 0.0252(10) -0.0008(9) 0.0171(10) 0.0046(11) C00V 0.0311(13) 0.0375(13) 0.0328(12) 0.0050(10) 0.0150(10) 0.0136(10) C00W 0.0319(13) 0.0376(13) 0.0292(11) 0.0086(10) 0.0196(10) 0.0083(10) C00X 0.0354(14) 0.0385(13) 0.0286(11) 0.0071(10) 0.0134(10) -0.0031(11) C00Y 0.0292(12) 0.0272(11) 0.0288(10) 0.0035(9) 0.0159(9) 0.0064(10) C00Z 0.0231(12) 0.0412(14) 0.0288(11) 0.0059(10) 0.0084(9) 0.0062(10) C010 0.0450(15) 0.0282(12) 0.0361(12) -0.0024(10) 0.0198(11) -0.0001(11) C011 0.0298(13) 0.0409(14) 0.0319(11) 0.0058(10) 0.0174(10) 0.0045(10) C012 0.0375(14) 0.0405(14) 0.0350(12) 0.0077(10) 0.0233(11) 0.0054(11) C013 0.0273(13) 0.0475(15) 0.0416(13) 0.0175(11) 0.0188(11) 0.0086(11) C014 0.0267(13) 0.0455(15) 0.0333(12) 0.0132(11) 0.0093(10) -0.0009(11) C015 0.0461(15) 0.0368(13) 0.0300(11) 0.0010(10) 0.0229(11) 0.0070(11) 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' 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 C005 N001 C007 117.65(16) . . ? C006 N002 C00E 117.93(16) . . ? C00F N003 C00M 118.14(15) . . ? C00F N003 C00Y 121.64(17) . . ? C00Y N003 C00M 120.20(17) . . ? C00D C004 C006 119.52(17) . . ? C00D C004 C00P 118.60(19) . . ? C00P C004 C006 121.83(18) . . ? N001 C005 C006 121.22(17) . . ? N001 C005 C00A 115.13(16) . . ? C006 C005 C00A 123.61(18) . . ? N002 C006 C004 115.90(16) . . ? N002 C006 C005 121.36(18) . . ? C005 C006 C004 122.73(16) . . ? N001 C007 C00E 121.47(18) . . ? N001 C007 C00R 119.36(16) . . ? C00R C007 C00E 119.16(17) . . ? C00G C008 C00J 120.63(17) . . ? C00G C008 C00L 117.89(18) . . ? C00L C008 C00J 121.33(18) . . ? C00A C009 H009 119.7 . . ? C00B C009 H009 119.7 . . ? C00B C009 C00A 120.60(19) . . ? C009 C00A C005 121.74(17) . . ? C009 C00A C00H 118.74(18) . . ? C00H C00A C005 119.31(18) . . ? C009 C00B H00B 120.0 . . ? C00W C00B C009 120.0(2) . . ? C00W C00B H00B 120.0 . . ? C00E C00C H00C 119.5 . . ? C00J C00C H00C 119.5 . . ? C00J C00C C00E 121.05(17) . . ? C004 C00D H00D 119.7 . . ? C00S C00D C004 120.64(19) . . ? C00S C00D H00D 119.7 . . ? N002 C00E C007 120.11(17) . . ? N002 C00E C00C 120.51(17) . . ? C00C C00E C007 119.35(18) . . ? C00N C00F N003 119.92(19) . . ? C00N C00F C011 118.9(2) . . ? C011 C00F N003 121.12(19) . . ? C008 C00G H00G 119.3 . . ? C00I C00G C008 121.49(18) . . ? C00I C00G H00G 119.3 . . ? C00A C00H H00H 119.6 . . ? C00U C00H C00A 120.8(2) . . ? C00U C00H H00H 119.6 . . ? C00G C00I H00I 120.1 . . ? C00G C00I C00M 119.89(19) . . ? C00M C00I H00I 120.1 . . ? C00C C00J C008 123.93(17) . . ? C00C C00J C00K 118.39(18) . . ? C00K C00J C008 117.64(18) . . ? C00J C00K H00K 119.3 . . ? C00R C00K C00J 121.47(19) . . ? C00R C00K H00K 119.3 . . ? C008 C00L H00L 119.6 . . ? C00O C00L C008 120.9(2) . . ? C00O C00L H00L 119.6 . . ? C00I C00M N003 119.89(19) . . ? C00O C00M N003 120.80(18) . . ? C00O C00M C00I 119.22(18) . . ? C00F C00N H00N 119.8 . . ? C00X C00N C00F 120.5(2) . . ? C00X C00N H00N 119.8 . . ? C00L C00O C00M 120.48(19) . . ? C00L C00O H00O 119.8 . . ? C00M C00O H00O 119.8 . . ? C004 C00P H00P 119.8 . . ? C00V C00P C004 120.49(19) . . ? C00V C00P H00P 119.8 . . ? C00Y C00Q H00Q 119.9 . . ? C012 C00Q H00Q 119.9 . . ? C012 C00Q C00Y 120.2(2) . . ? C007 C00R H00R 119.7 . . ? C00K C00R C007 120.57(18) . . ? C00K C00R H00R 119.7 . . ? C00D C00S H00S 119.9 . . ? C00Z C00S C00D 120.2(2) . . ? C00Z C00S H00S 119.9 . . ? C00Y C00T H00T 119.9 . . ? C010 C00T H00T 119.9 . . ? C010 C00T C00Y 120.3(2) . . ? C00H C00U H00U 120.1 . . ? C00H C00U C00W 119.82(19) . . ? C00W C00U H00U 120.1 . . ? C00P C00V H00V 119.8 . . ? C00Z C00V C00P 120.3(2) . . ? C00Z C00V H00V 119.8 . . ? C00B C00W C00U 120.06(19) . . ? C00B C00W H00W 120.0 . . ? C00U C00W H00W 120.0 . . ? C00N C00X H00X 119.8 . . ? C014 C00X C00N 120.4(2) . . ? C014 C00X H00X 119.8 . . ? C00Q C00Y N003 120.7(2) . . ? C00T C00Y N003 120.50(19) . . ? C00T C00Y C00Q 118.85(19) . . ? C00S C00Z H00Z 120.1 . . ? C00V C00Z C00S 119.8(2) . . ? C00V C00Z H00Z 120.1 . . ? C00T C010 H010 119.6 . . ? C00T C010 C015 120.8(2) . . ? C015 C010 H010 119.6 . . ? C00F C011 H011 120.0 . . ? C013 C011 C00F 120.1(2) . . ? C013 C011 H011 120.0 . . ? C00Q C012 H012 119.7 . . ? C015 C012 C00Q 120.6(2) . . ? C015 C012 H012 119.7 . . ? C011 C013 H013 119.6 . . ? C014 C013 C011 120.9(2) . . ? C014 C013 H013 119.6 . . ? C00X C014 H014 120.4 . . ? C013 C014 C00X 119.3(2) . . ? C013 C014 H014 120.4 . . ? C010 C015 C012 119.2(2) . . ? C010 C015 H015 120.4 . . ? C012 C015 H015 120.4 . . ? 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 N001 C005 1.317(2) . ? N001 C007 1.364(2) . ? N002 C006 1.322(2) . ? N002 C00E 1.368(2) . ? N003 C00F 1.417(3) . ? N003 C00M 1.426(3) . ? N003 C00Y 1.418(2) . ? C004 C006 1.487(3) . ? C004 C00D 1.391(3) . ? C004 C00P 1.397(3) . ? C005 C006 1.441(2) . ? C005 C00A 1.488(3) . ? C007 C00E 1.413(3) . ? C007 C00R 1.400(3) . ? C008 C00G 1.395(3) . ? C008 C00J 1.483(3) . ? C008 C00L 1.399(3) . ? C009 H009 0.9500 . ? C009 C00A 1.390(3) . ? C009 C00B 1.387(3) . ? C00A C00H 1.399(3) . ? C00B H00B 0.9500 . ? C00B C00W 1.386(3) . ? C00C H00C 0.9500 . ? C00C C00E 1.413(3) . ? C00C C00J 1.372(3) . ? C00D H00D 0.9500 . ? C00D C00S 1.384(3) . ? C00F C00N 1.392(3) . ? C00F C011 1.394(3) . ? C00G H00G 0.9500 . ? C00G C00I 1.385(3) . ? C00H H00H 0.9500 . ? C00H C00U 1.381(3) . ? C00I H00I 0.9500 . ? C00I C00M 1.395(3) . ? C00J C00K 1.427(3) . ? C00K H00K 0.9500 . ? C00K C00R 1.357(3) . ? C00L H00L 0.9500 . ? C00L C00O 1.386(3) . ? C00M C00O 1.389(3) . ? C00N H00N 0.9500 . ? C00N C00X 1.386(3) . ? C00O H00O 0.9500 . ? C00P H00P 0.9500 . ? C00P C00V 1.383(3) . ? C00Q H00Q 0.9500 . ? C00Q C00Y 1.399(3) . ? C00Q C012 1.385(3) . ? C00R H00R 0.9500 . ? C00S H00S 0.9500 . ? C00S C00Z 1.383(3) . ? C00T H00T 0.9500 . ? C00T C00Y 1.393(3) . ? C00T C010 1.382(3) . ? C00U H00U 0.9500 . ? C00U C00W 1.387(3) . ? C00V H00V 0.9500 . ? C00V C00Z 1.380(3) . ? C00W H00W 0.9500 . ? C00X H00X 0.9500 . ? C00X C014 1.384(3) . ? C00Z H00Z 0.9500 . ? C010 H010 0.9500 . ? C010 C015 1.383(3) . ? C011 H011 0.9500 . ? C011 C013 1.385(3) . ? C012 H012 0.9500 . ? C012 C015 1.384(3) . ? C013 H013 0.9500 . ? C013 C014 1.382(3) . ? C014 H014 0.9500 . ? C015 H015 0.9500 . ? 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 N001 C005 C006 N002 -5.2(3) . . . . ? N001 C005 C006 C004 173.86(18) . . . . ? N001 C005 C00A C009 130.0(2) . . . . ? N001 C005 C00A C00H -44.8(3) . . . . ? N001 C007 C00E N002 -4.3(3) . . . . ? N001 C007 C00E C00C 177.85(19) . . . . ? N001 C007 C00R C00K -177.5(2) . . . . ? N003 C00F C00N C00X -177.26(19) . . . . ? N003 C00F C011 C013 178.38(19) . . . . ? N003 C00M C00O C00L 175.0(2) . . . . ? C004 C00D C00S C00Z -0.8(3) . . . . ? C004 C00P C00V C00Z -0.4(3) . . . . ? C005 N001 C007 C00E 2.9(3) . . . . ? C005 N001 C007 C00R -178.38(19) . . . . ? C005 C00A C00H C00U 175.74(19) . . . . ? C006 N002 C00E C007 0.8(3) . . . . ? C006 N002 C00E C00C 178.59(19) . . . . ? C006 C004 C00D C00S 178.10(18) . . . . ? C006 C004 C00P C00V -177.40(19) . . . . ? C006 C005 C00A C009 -47.9(3) . . . . ? C006 C005 C00A C00H 137.4(2) . . . . ? C007 N001 C005 C006 1.6(3) . . . . ? C007 N001 C005 C00A -176.29(17) . . . . ? C008 C00G C00I C00M -1.7(3) . . . . ? C008 C00J C00K C00R -178.2(2) . . . . ? C008 C00L C00O C00M -2.0(3) . . . . ? C009 C00A C00H C00U 0.8(3) . . . . ? C009 C00B C00W C00U 0.4(3) . . . . ? C00A C005 C006 N002 172.53(19) . . . . ? C00A C005 C006 C004 -8.4(3) . . . . ? C00A C009 C00B C00W -1.3(3) . . . . ? C00A C00H C00U C00W -1.6(3) . . . . ? C00B C009 C00A C005 -174.15(19) . . . . ? C00B C009 C00A C00H 0.7(3) . . . . ? C00C C00J C00K C00R -0.4(3) . . . . ? C00D C004 C006 N002 -47.0(3) . . . . ? C00D C004 C006 C005 133.9(2) . . . . ? C00D C004 C00P C00V -0.1(3) . . . . ? C00D C00S C00Z C00V 0.3(3) . . . . ? C00E N002 C006 C004 -175.37(17) . . . . ? C00E N002 C006 C005 3.8(3) . . . . ? C00E C007 C00R C00K 1.2(3) . . . . ? C00E C00C C00J C008 178.36(19) . . . . ? C00E C00C C00J C00K 0.8(3) . . . . ? C00F N003 C00M C00I 47.5(3) . . . . ? C00F N003 C00M C00O -129.1(2) . . . . ? C00F N003 C00Y C00Q 35.5(3) . . . . ? C00F N003 C00Y C00T -144.3(2) . . . . ? C00F C00N C00X C014 -1.1(3) . . . . ? C00F C011 C013 C014 -1.2(3) . . . . ? C00G C008 C00J C00C 144.2(2) . . . . ? C00G C008 C00J C00K -38.2(3) . . . . ? C00G C008 C00L C00O 3.7(3) . . . . ? C00G C00I C00M N003 -173.21(19) . . . . ? C00G C00I C00M C00O 3.4(3) . . . . ? C00H C00U C00W C00B 1.0(3) . . . . ? C00I C00M C00O C00L -1.7(3) . . . . ? C00J C008 C00G C00I 173.66(19) . . . . ? C00J C008 C00L C00O -171.8(2) . . . . ? C00J C00C C00E N002 -177.96(19) . . . . ? C00J C00C C00E C007 -0.1(3) . . . . ? C00J C00K C00R C007 -0.5(3) . . . . ? C00L C008 C00G C00I -1.9(3) . . . . ? C00L C008 C00J C00C -40.4(3) . . . . ? C00L C008 C00J C00K 137.2(2) . . . . ? C00M N003 C00F C00N 35.3(3) . . . . ? C00M N003 C00F C011 -143.2(2) . . . . ? C00M N003 C00Y C00Q -146.5(2) . . . . ? C00M N003 C00Y C00T 33.7(3) . . . . ? C00N C00F C011 C013 -0.1(3) . . . . ? C00N C00X C014 C013 -0.2(3) . . . . ? C00P C004 C006 N002 130.3(2) . . . . ? C00P C004 C006 C005 -48.8(3) . . . . ? C00P C004 C00D C00S 0.7(3) . . . . ? C00P C00V C00Z C00S 0.3(3) . . . . ? C00Q C012 C015 C010 -0.3(3) . . . . ? C00R C007 C00E N002 177.00(19) . . . . ? C00R C007 C00E C00C -0.8(3) . . . . ? C00T C010 C015 C012 1.6(4) . . . . ? C00Y N003 C00F C00N -146.7(2) . . . . ? C00Y N003 C00F C011 34.8(3) . . . . ? C00Y N003 C00M C00I -130.6(2) . . . . ? C00Y N003 C00M C00O 52.8(3) . . . . ? C00Y C00Q C012 C015 -1.3(3) . . . . ? C00Y C00T C010 C015 -1.1(3) . . . . ? C010 C00T C00Y N003 179.3(2) . . . . ? C010 C00T C00Y C00Q -0.5(3) . . . . ? C011 C00F C00N C00X 1.3(3) . . . . ? C011 C013 C014 C00X 1.3(3) . . . . ? C012 C00Q C00Y N003 -178.0(2) . . . . ? C012 C00Q C00Y C00T 1.8(3) . . . . ?