#------------------------------------------------------------------------------ #$Date: 2021-07-05 21:06:10 +0300 (Mon, 05 Jul 2021) $ #$Revision: 267222 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/06/06/7060686.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_7060686 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_issue 25 _journal_name_full 'New Journal of Chemistry' _journal_page_first 11304 _journal_page_last 11312 _journal_paper_doi 10.1039/D1NJ01350E _journal_volume 45 _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 2021-04-02 _audit_creation_method ; Olex2 1.3 (compiled 2020.11.12 svn.r5f609507 for OlexSys, GUI svn.r6272) ; _audit_update_record ; 2021-04-03 deposited with the CCDC. 2021-05-19 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 117.001(3) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 19.2475(18) _cell_length_b 8.9360(8) _cell_length_c 18.0898(19) _cell_measurement_reflns_used 5026 _cell_measurement_temperature 296.15 _cell_measurement_theta_max 27.38 _cell_measurement_theta_min 2.25 _cell_volume 2772.2(5) _computing_cell_refinement 'SAINT V8.40A (Bruker, 2019)' _computing_data_reduction 'SAINT V8.40A (Bruker, 2019)' _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 2014/5 (Sheldrick, 2014)' _diffrn_ambient_temperature 296.15 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.995 _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 0.0822 _diffrn_reflns_av_unetI/netI 0.0735 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.995 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_limit_l_min -23 _diffrn_reflns_number 24619 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.995 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 27.499 _diffrn_reflns_theta_min 2.252 _diffrn_source_current 40.0 _diffrn_source_power 2.0 _diffrn_source_voltage 50.0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.074 _exptl_absorpt_correction_T_max 0.7456 _exptl_absorpt_correction_T_min 0.5562 _exptl_absorpt_correction_type none _exptl_absorpt_process_details ; SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1516 before and 0.0787 after correction. The Ratio of minimum to maximum transmission is 0.7460. The \l/2 correction factor is Not present. ; _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.259 _exptl_crystal_description block _exptl_crystal_F_000 1104 _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.15 _exptl_crystal_size_min 0.10 _refine_diff_density_max 0.243 _refine_diff_density_min -0.228 _refine_diff_density_rms 0.045 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.022 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 370 _refine_ls_number_reflns 6337 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.022 _refine_ls_R_factor_all 0.0921 _refine_ls_R_factor_gt 0.0528 _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^)+(0.0475P)^2^+0.5056P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1179 _refine_ls_wR_factor_ref 0.1370 _reflns_Friedel_coverage 0.000 _reflns_number_gt 4049 _reflns_number_total 6337 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d1nj01350e2.cif _cod_data_source_block a _cod_depositor_comments 'Adding full bibliography for 7060684--7060687.cif.' _cod_database_code 7060686 _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. ; _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups 2.a Aromatic/amide H refined with riding coordinates: C00A(H00A), C00B(H00B), C00D(H00D), C00E(H00E), C00F(H00F), C00G(H00G), C00K(H00K), C00L(H00L), C00M(H00M), C00N(H00N), C00O(H00O), C00P(H00P), C00Q(H00Q), C00S(H00S), C00T(H00T), C00U(H00U), C00V(H00V), C00W(H00W), C00X(H00X), C00Y(H00Y), C00Z(H00Z), C010(H010), C011(H011), C012(H012), C013(H013), C014(H014), C015(H015) ; _shelx_res_file ; TITL a_a.res in P2(1)/c a.res created by SHELXL-2018/3 at 21:09:42 on 02-Apr-2021 REM Old TITL A in P2(1)/c REM SHELXT solution in P2(1)/c REM R1 0.157, Rweak 0.007, Alpha 0.031, Orientation as input REM Formula found by SHELXT: C38 N3 CELL 0.71073 19.2475 8.936 18.0898 90 117.001 90 ZERR 4 0.0018 0.0008 0.0019 0 0.003 0 LATT 1 SYMM -X,0.5+Y,0.5-Z SFAC C H N UNIT 152 108 12 L.S. 20 123 PLAN 5 TEMP 23 CONF BOND $H list 4 MORE -1 fmap 2 ACTA REM REM REM WGHT 0.047500 0.505600 FVAR 0.45272 N001 3 0.667352 0.331496 0.537275 11.00000 0.03024 0.03703 = 0.02881 -0.00093 0.01581 -0.00324 N002 3 0.732724 0.337758 0.711789 11.00000 0.02797 0.04146 = 0.02712 0.00041 0.01483 0.00072 N003 3 0.292120 0.319018 0.768497 11.00000 0.03131 0.06008 = 0.03373 0.00085 0.01995 -0.00108 C004 1 0.862008 0.309535 0.727609 11.00000 0.03054 0.03500 = 0.02513 0.00541 0.01677 0.00237 C005 1 0.776868 0.326911 0.673042 11.00000 0.03031 0.03065 = 0.02739 0.00160 0.01614 -0.00049 C006 1 0.743682 0.329651 0.584040 11.00000 0.03103 0.02903 = 0.02661 -0.00083 0.01587 -0.00203 C007 1 0.468019 0.355506 0.690542 11.00000 0.02851 0.03513 = 0.03310 0.00270 0.01705 -0.00022 C008 1 0.621569 0.334889 0.577103 11.00000 0.03059 0.03292 = 0.03000 0.00066 0.01709 -0.00065 C009 1 0.790614 0.335600 0.537430 11.00000 0.03135 0.03179 = 0.02436 0.00338 0.01562 0.00242 C00A 1 0.898572 0.403186 0.795609 11.00000 0.03073 0.03651 = 0.03002 0.00031 0.01609 0.00302 AFIX 43 H00A 2 0.870022 0.477245 0.805736 11.00000 -1.20000 AFIX 0 C00B 1 0.889365 0.450257 0.509323 11.00000 0.03308 0.04089 = 0.03987 0.00801 0.02064 0.00199 AFIX 43 H00B 2 0.929136 0.520070 0.522862 11.00000 -1.20000 AFIX 0 C00C 1 0.653654 0.342604 0.663848 11.00000 0.02801 0.03378 = 0.02897 0.00077 0.01468 -0.00032 C00D 1 0.398006 0.434825 0.650504 11.00000 0.03369 0.03471 = 0.03313 0.00685 0.01785 0.00085 AFIX 43 H00D 2 0.388959 0.493075 0.604403 11.00000 -1.20000 AFIX 0 C00E 1 0.851045 0.437744 0.558019 11.00000 0.03155 0.03394 = 0.03276 0.00093 0.01690 -0.00052 AFIX 43 H00E 2 0.865850 0.497982 0.604675 11.00000 -1.20000 AFIX 0 C00F 1 0.603620 0.350756 0.701948 11.00000 0.03123 0.04350 = 0.02813 -0.00025 0.01641 0.00110 AFIX 43 H00F 2 0.624798 0.355688 0.759444 11.00000 -1.20000 AFIX 0 C00G 1 0.342224 0.428023 0.678290 11.00000 0.02903 0.03750 = 0.03683 0.00572 0.01584 0.00457 AFIX 43 H00G 2 0.296782 0.484099 0.651891 11.00000 -1.20000 AFIX 0 C00H 1 0.216769 0.284215 0.704794 11.00000 0.03029 0.04524 = 0.03544 0.00959 0.01928 0.00263 C00I 1 0.353299 0.338111 0.745397 11.00000 0.02899 0.04229 = 0.03271 0.00148 0.01823 0.00064 C00J 1 0.523863 0.351422 0.654402 11.00000 0.02928 0.03473 = 0.03422 0.00218 0.01759 -0.00046 C00K 1 0.493055 0.341692 0.567165 11.00000 0.02833 0.04561 = 0.03377 0.00294 0.01404 -0.00150 AFIX 43 H00K 2 0.439245 0.341677 0.534793 11.00000 -1.20000 AFIX 0 C00L 1 0.905265 0.198448 0.713917 11.00000 0.04073 0.03972 = 0.03333 -0.00093 0.01788 0.00588 AFIX 43 H00L 2 0.881463 0.135000 0.668486 11.00000 -1.20000 AFIX 0 C00M 1 0.769898 0.245816 0.467632 11.00000 0.03685 0.04069 = 0.03408 -0.00313 0.01989 -0.00452 AFIX 43 H00M 2 0.729097 0.177962 0.452758 11.00000 -1.20000 AFIX 0 C00N 1 0.540123 0.332302 0.529015 11.00000 0.03152 0.04925 = 0.02630 -0.00041 0.01214 -0.00107 AFIX 43 H00N 2 0.518359 0.324250 0.471582 11.00000 -1.20000 AFIX 0 C00O 1 0.359828 0.445632 0.901785 11.00000 0.05015 0.03698 = 0.04530 0.00377 0.03037 0.00226 AFIX 43 H00O 2 0.386999 0.503422 0.880785 11.00000 -1.20000 AFIX 0 C00P 1 0.208450 0.192698 0.639510 11.00000 0.03588 0.04614 = 0.04123 0.00757 0.02278 0.00142 AFIX 43 H00P 2 0.252424 0.150726 0.638952 11.00000 -1.20000 AFIX 0 C00Q 1 0.977490 0.387086 0.848637 11.00000 0.03379 0.04332 = 0.03108 0.00029 0.01236 0.00132 AFIX 43 H00Q 2 1.001738 0.451127 0.893724 11.00000 -1.20000 AFIX 0 C00R 1 0.306514 0.339545 0.851755 11.00000 0.03849 0.03913 = 0.03424 0.00437 0.02209 0.00670 C00S 1 0.868616 0.359190 0.440642 11.00000 0.03903 0.04843 = 0.03840 0.01106 0.02562 0.01001 AFIX 43 H00S 2 0.894645 0.367280 0.408291 11.00000 -1.20000 AFIX 0 C00T 1 0.480360 0.273078 0.760349 11.00000 0.03008 0.04914 = 0.03676 0.01077 0.01600 0.00784 AFIX 43 H00T 2 0.527700 0.224102 0.789818 11.00000 -1.20000 AFIX 0 C00U 1 0.809280 0.256435 0.420261 11.00000 0.04681 0.04766 = 0.03068 -0.00287 0.02273 0.00508 AFIX 43 H00U 2 0.795759 0.194206 0.374566 11.00000 -1.20000 AFIX 0 C00V 1 0.983838 0.181887 0.767798 11.00000 0.04262 0.05094 = 0.03999 0.00453 0.02086 0.01728 AFIX 43 H00V 2 1.012310 0.106342 0.758708 11.00000 -1.20000 AFIX 0 C00W 1 0.423398 0.262215 0.787134 11.00000 0.03814 0.04978 = 0.03253 0.01144 0.01977 0.00630 AFIX 43 H00W 2 0.432257 0.203919 0.833165 11.00000 -1.20000 AFIX 0 C00X 1 0.266975 0.253648 0.885468 11.00000 0.04127 0.04847 = 0.04192 0.00348 0.02484 -0.00048 AFIX 43 H00X 2 0.231845 0.180666 0.853196 11.00000 -1.20000 AFIX 0 C00Y 1 0.135277 0.162861 0.574906 11.00000 0.04549 0.05016 = 0.03777 0.00644 0.01837 -0.00389 AFIX 43 H00Y 2 0.130578 0.103223 0.530740 11.00000 -1.20000 AFIX 0 C00Z 1 1.020118 0.276307 0.834672 11.00000 0.03029 0.05236 = 0.03886 0.00773 0.01455 0.00812 AFIX 43 H00Z 2 1.073016 0.265507 0.870210 11.00000 -1.20000 AFIX 0 C010 1 0.372620 0.465547 0.982936 11.00000 0.06056 0.03750 = 0.04690 -0.00416 0.02954 0.00163 AFIX 43 H010 2 0.409002 0.535976 1.016100 11.00000 -1.20000 AFIX 0 C011 1 0.279670 0.276307 0.966442 11.00000 0.04604 0.05436 = 0.04119 0.00945 0.02826 0.00395 AFIX 43 H011 2 0.252497 0.219375 0.987790 11.00000 -1.20000 AFIX 0 C012 1 0.149871 0.342809 0.705761 11.00000 0.04070 0.05315 = 0.04528 0.00994 0.02728 0.00756 AFIX 43 H012 2 0.154227 0.404242 0.749157 11.00000 -1.20000 AFIX 0 C013 1 0.332354 0.382762 1.015626 11.00000 0.05937 0.05169 = 0.03960 0.00488 0.03226 0.01361 AFIX 43 H013 2 0.340639 0.398563 1.069832 11.00000 -1.20000 AFIX 0 C014 1 0.069386 0.221635 0.576103 11.00000 0.03532 0.06103 = 0.04300 0.01851 0.01356 -0.00084 AFIX 43 H014 2 0.020249 0.202267 0.532834 11.00000 -1.20000 AFIX 0 C015 1 0.077354 0.309292 0.642180 11.00000 0.03319 0.06542 = 0.05198 0.02222 0.02324 0.01140 AFIX 43 H015 2 0.033012 0.346546 0.643939 11.00000 -1.20000 AFIX 0 HKLF 4 REM a_a.res in P2(1)/c REM wR2 = 0.1370, GooF = S = 1.022, Restrained GooF = 1.022 for all data REM R1 = 0.0528 for 4049 Fo > 4sig(Fo) and 0.0921 for all 6337 data REM 370 parameters refined using 0 restraints END WGHT 0.0474 0.5059 REM Highest difference peak 0.243, deepest hole -0.228, 1-sigma level 0.045 Q1 1 0.4964 0.3541 0.6721 11.00000 0.05 0.24 Q2 1 0.7665 0.3320 0.4895 11.00000 0.05 0.21 Q3 1 0.7693 0.3336 0.5618 11.00000 0.05 0.19 Q4 1 0.6280 0.3249 0.6801 11.00000 0.05 0.19 Q5 1 0.0400 0.4147 0.6680 11.00000 0.05 0.19 ; _shelx_res_checksum 38800 _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 0.66735(8) 0.33150(16) 0.53727(10) 0.0311(3) Uani 1 1 d . . . . . N002 N 0.73272(8) 0.33776(16) 0.71179(9) 0.0313(4) Uani 1 1 d . . . . . N003 N 0.29212(9) 0.31902(19) 0.76850(11) 0.0397(4) Uani 1 1 d . . . . . C004 C 0.86201(10) 0.30953(19) 0.72761(11) 0.0287(4) Uani 1 1 d . . . . . C005 C 0.77687(10) 0.32691(18) 0.67304(11) 0.0283(4) Uani 1 1 d . . . . . C006 C 0.74368(10) 0.32965(19) 0.58404(11) 0.0278(4) Uani 1 1 d . . . . . C007 C 0.46802(10) 0.3555(2) 0.69054(12) 0.0311(4) Uani 1 1 d . . . . . C008 C 0.62157(10) 0.33489(19) 0.57710(12) 0.0299(4) Uani 1 1 d . . . . . C009 C 0.79061(10) 0.33560(19) 0.53743(11) 0.0280(4) Uani 1 1 d . . . . . C00A C 0.89857(10) 0.4032(2) 0.79561(11) 0.0315(4) Uani 1 1 d . . . . . H00A H 0.870022 0.477245 0.805736 0.038 Uiso 1 1 calc R U . . . C00B C 0.88937(10) 0.4503(2) 0.50932(13) 0.0364(5) Uani 1 1 d . . . . . H00B H 0.929136 0.520070 0.522862 0.044 Uiso 1 1 calc R U . . . C00C C 0.65365(10) 0.34260(19) 0.66385(12) 0.0296(4) Uani 1 1 d . . . . . C00D C 0.39801(10) 0.4348(2) 0.65050(12) 0.0328(4) Uani 1 1 d . . . . . H00D H 0.388959 0.493075 0.604403 0.039 Uiso 1 1 calc R U . . . C00E C 0.85104(10) 0.43774(19) 0.55802(12) 0.0319(4) Uani 1 1 d . . . . . H00E H 0.865850 0.497982 0.604675 0.038 Uiso 1 1 calc R U . . . C00F C 0.60362(10) 0.3508(2) 0.70195(12) 0.0332(4) Uani 1 1 d . . . . . H00F H 0.624798 0.355688 0.759444 0.040 Uiso 1 1 calc R U . . . C00G C 0.34222(10) 0.4280(2) 0.67829(12) 0.0341(4) Uani 1 1 d . . . . . H00G H 0.296782 0.484099 0.651891 0.041 Uiso 1 1 calc R U . . . C00H C 0.21677(10) 0.2842(2) 0.70479(12) 0.0353(4) Uani 1 1 d . . . . . C00I C 0.35330(10) 0.3381(2) 0.74540(12) 0.0331(4) Uani 1 1 d . . . . . C00J C 0.52386(10) 0.3514(2) 0.65440(12) 0.0315(4) Uani 1 1 d . . . . . C00K C 0.49305(10) 0.3417(2) 0.56717(12) 0.0359(4) Uani 1 1 d . . . . . H00K H 0.439245 0.341677 0.534793 0.043 Uiso 1 1 calc R U . . . C00L C 0.90527(11) 0.1984(2) 0.71392(13) 0.0375(5) Uani 1 1 d . . . . . H00L H 0.881463 0.135000 0.668486 0.045 Uiso 1 1 calc R U . . . C00M C 0.76990(10) 0.2458(2) 0.46763(12) 0.0358(4) Uani 1 1 d . . . . . H00M H 0.729097 0.177962 0.452758 0.043 Uiso 1 1 calc R U . . . C00N C 0.54012(10) 0.3323(2) 0.52902(12) 0.0361(4) Uani 1 1 d . . . . . H00N H 0.518359 0.324250 0.471582 0.043 Uiso 1 1 calc R U . . . C00O C 0.35983(11) 0.4456(2) 0.90178(13) 0.0408(5) Uani 1 1 d . . . . . H00O H 0.386999 0.503422 0.880785 0.049 Uiso 1 1 calc R U . . . C00P C 0.20845(11) 0.1927(2) 0.63951(13) 0.0391(5) Uani 1 1 d . . . . . H00P H 0.252424 0.150726 0.638952 0.047 Uiso 1 1 calc R U . . . C00Q C 0.97749(10) 0.3871(2) 0.84864(12) 0.0370(5) Uani 1 1 d . . . . . H00Q H 1.001738 0.451127 0.893724 0.044 Uiso 1 1 calc R U . . . C00R C 0.30651(11) 0.3395(2) 0.85175(13) 0.0352(4) Uani 1 1 d . . . . . C00S C 0.86862(11) 0.3592(2) 0.44064(13) 0.0389(5) Uani 1 1 d . . . . . H00S H 0.894645 0.367280 0.408291 0.047 Uiso 1 1 calc R U . . . C00T C 0.48036(10) 0.2731(2) 0.76035(13) 0.0383(5) Uani 1 1 d . . . . . H00T H 0.527700 0.224102 0.789818 0.046 Uiso 1 1 calc R U . . . C00U C 0.80928(11) 0.2564(2) 0.42026(13) 0.0398(5) Uani 1 1 d . . . . . H00U H 0.795759 0.194206 0.374566 0.048 Uiso 1 1 calc R U . . . C00V C 0.98384(11) 0.1819(2) 0.76780(13) 0.0437(5) Uani 1 1 d . . . . . H00V H 1.012310 0.106342 0.758708 0.052 Uiso 1 1 calc R U . . . C00W C 0.42340(10) 0.2622(2) 0.78713(13) 0.0387(5) Uani 1 1 d . . . . . H00W H 0.432257 0.203919 0.833165 0.046 Uiso 1 1 calc R U . . . C00X C 0.26697(11) 0.2536(2) 0.88547(13) 0.0416(5) Uani 1 1 d . . . . . H00X H 0.231845 0.180666 0.853196 0.050 Uiso 1 1 calc R U . . . C00Y C 0.13528(11) 0.1629(2) 0.57491(14) 0.0447(5) Uani 1 1 d . . . . . H00Y H 0.130578 0.103223 0.530740 0.054 Uiso 1 1 calc R U . . . C00Z C 1.02012(11) 0.2763(2) 0.83467(13) 0.0409(5) Uani 1 1 d . . . . . H00Z H 1.073016 0.265507 0.870210 0.049 Uiso 1 1 calc R U . . . C010 C 0.37262(12) 0.4655(2) 0.98294(14) 0.0464(5) Uani 1 1 d . . . . . H010 H 0.409002 0.535976 1.016100 0.056 Uiso 1 1 calc R U . . . C011 C 0.27967(12) 0.2763(2) 0.96644(13) 0.0440(5) Uani 1 1 d . . . . . H011 H 0.252497 0.219375 0.987790 0.053 Uiso 1 1 calc R U . . . C012 C 0.14987(11) 0.3428(2) 0.70576(14) 0.0434(5) Uani 1 1 d . . . . . H012 H 0.154227 0.404242 0.749157 0.052 Uiso 1 1 calc R U . . . C013 C 0.33235(12) 0.3828(2) 1.01563(14) 0.0465(5) Uani 1 1 d . . . . . H013 H 0.340639 0.398563 1.069832 0.056 Uiso 1 1 calc R U . . . C014 C 0.06939(12) 0.2216(3) 0.57610(14) 0.0481(6) Uani 1 1 d . . . . . H014 H 0.020249 0.202267 0.532834 0.058 Uiso 1 1 calc R U . . . C015 C 0.07735(11) 0.3093(3) 0.64218(15) 0.0487(6) Uani 1 1 d . . . . . H015 H 0.033012 0.346546 0.643939 0.058 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 0.0302(8) 0.0370(8) 0.0288(9) -0.0009(7) 0.0158(7) -0.0032(6) N002 0.0280(7) 0.0415(9) 0.0271(9) 0.0004(7) 0.0148(7) 0.0007(6) N003 0.0313(8) 0.0601(11) 0.0337(10) 0.0008(8) 0.0199(7) -0.0011(7) C004 0.0305(9) 0.0350(9) 0.0251(10) 0.0054(8) 0.0168(8) 0.0024(7) C005 0.0303(9) 0.0307(9) 0.0274(10) 0.0016(7) 0.0161(8) -0.0005(7) C006 0.0310(9) 0.0290(9) 0.0266(10) -0.0008(7) 0.0159(8) -0.0020(7) C007 0.0285(9) 0.0351(9) 0.0331(11) 0.0027(8) 0.0171(8) -0.0002(7) C008 0.0306(9) 0.0329(9) 0.0300(11) 0.0007(8) 0.0171(8) -0.0006(7) C009 0.0314(9) 0.0318(9) 0.0244(10) 0.0034(7) 0.0156(8) 0.0024(7) C00A 0.0307(9) 0.0365(10) 0.0300(11) 0.0003(8) 0.0161(8) 0.0030(8) C00B 0.0331(10) 0.0409(10) 0.0399(12) 0.0080(9) 0.0206(9) 0.0020(8) C00C 0.0280(9) 0.0338(9) 0.0290(11) 0.0008(8) 0.0147(8) -0.0003(7) C00D 0.0337(9) 0.0347(10) 0.0331(11) 0.0069(8) 0.0179(8) 0.0008(8) C00E 0.0316(9) 0.0339(10) 0.0328(11) 0.0009(8) 0.0169(8) -0.0005(8) C00F 0.0312(9) 0.0435(10) 0.0281(11) -0.0002(8) 0.0164(8) 0.0011(8) C00G 0.0290(9) 0.0375(10) 0.0368(12) 0.0057(9) 0.0158(8) 0.0046(8) C00H 0.0303(9) 0.0452(11) 0.0354(12) 0.0096(9) 0.0193(8) 0.0026(8) C00I 0.0290(9) 0.0423(10) 0.0327(11) 0.0015(9) 0.0182(8) 0.0006(8) C00J 0.0293(9) 0.0347(9) 0.0342(11) 0.0022(8) 0.0176(8) -0.0005(7) C00K 0.0283(9) 0.0456(11) 0.0338(11) 0.0029(9) 0.0140(8) -0.0015(8) C00L 0.0407(11) 0.0397(10) 0.0333(12) -0.0009(9) 0.0179(9) 0.0059(8) C00M 0.0369(10) 0.0407(10) 0.0341(12) -0.0031(9) 0.0199(9) -0.0045(8) C00N 0.0315(10) 0.0493(11) 0.0263(11) -0.0004(9) 0.0121(8) -0.0011(8) C00O 0.0501(12) 0.0370(10) 0.0453(13) 0.0038(9) 0.0304(10) 0.0023(9) C00P 0.0359(10) 0.0461(11) 0.0412(13) 0.0076(9) 0.0228(9) 0.0014(9) C00Q 0.0338(10) 0.0433(11) 0.0311(12) 0.0003(9) 0.0124(8) 0.0013(8) C00R 0.0385(10) 0.0391(10) 0.0342(11) 0.0044(9) 0.0221(9) 0.0067(8) C00S 0.0390(10) 0.0484(11) 0.0384(12) 0.0111(10) 0.0256(9) 0.0100(9) C00T 0.0301(9) 0.0491(11) 0.0368(12) 0.0108(9) 0.0160(8) 0.0078(8) C00U 0.0468(11) 0.0477(12) 0.0307(11) -0.0029(9) 0.0227(9) 0.0051(9) C00V 0.0426(11) 0.0509(12) 0.0400(13) 0.0045(10) 0.0209(10) 0.0173(9) C00W 0.0381(10) 0.0498(11) 0.0325(12) 0.0114(9) 0.0198(9) 0.0063(9) C00X 0.0413(11) 0.0485(12) 0.0419(13) 0.0035(10) 0.0248(10) -0.0005(9) C00Y 0.0455(12) 0.0502(12) 0.0378(13) 0.0064(10) 0.0184(10) -0.0039(10) C00Z 0.0303(9) 0.0524(12) 0.0389(13) 0.0077(10) 0.0145(9) 0.0081(9) C010 0.0606(13) 0.0375(11) 0.0469(14) -0.0042(10) 0.0295(11) 0.0016(10) C011 0.0460(11) 0.0544(13) 0.0412(13) 0.0095(10) 0.0283(10) 0.0039(10) C012 0.0407(11) 0.0531(12) 0.0453(13) 0.0099(10) 0.0273(10) 0.0076(9) C013 0.0594(13) 0.0517(12) 0.0396(13) 0.0049(10) 0.0323(11) 0.0136(11) C014 0.0353(11) 0.0610(14) 0.0430(14) 0.0185(11) 0.0136(10) -0.0008(10) C015 0.0332(10) 0.0654(14) 0.0520(15) 0.0222(12) 0.0232(10) 0.0114(10) 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 C006 N001 C008 117.24(16) . . ? C005 N002 C00C 117.51(16) . . ? C00H N003 C00I 117.63(16) . . ? C00R N003 C00H 121.84(15) . . ? C00R N003 C00I 120.50(16) . . ? C00A C004 C005 119.21(15) . . ? C00A C004 C00L 119.07(16) . . ? C00L C004 C005 121.68(17) . . ? N002 C005 C004 115.67(16) . . ? N002 C005 C006 121.63(16) . . ? C006 C005 C004 122.69(15) . . ? N001 C006 C005 121.11(15) . . ? N001 C006 C009 114.88(16) . . ? C005 C006 C009 123.98(15) . . ? C00D C007 C00J 120.15(17) . . ? C00T C007 C00D 117.86(16) . . ? C00T C007 C00J 121.81(16) . . ? N001 C008 C00C 121.88(16) . . ? N001 C008 C00N 118.52(17) . . ? C00C C008 C00N 119.59(16) . . ? C00E C009 C006 121.35(16) . . ? C00E C009 C00M 118.79(16) . . ? C00M C009 C006 119.65(16) . . ? C004 C00A H00A 119.8 . . ? C004 C00A C00Q 120.41(17) . . ? C00Q C00A H00A 119.8 . . ? C00E C00B H00B 119.9 . . ? C00S C00B H00B 119.9 . . ? C00S C00B C00E 120.20(18) . . ? N002 C00C C008 120.37(15) . . ? N002 C00C C00F 119.94(17) . . ? C008 C00C C00F 119.67(16) . . ? C007 C00D H00D 119.5 . . ? C00G C00D C007 121.05(18) . . ? C00G C00D H00D 119.5 . . ? C009 C00E H00E 119.8 . . ? C00B C00E C009 120.31(18) . . ? C00B C00E H00E 119.8 . . ? C00C C00F H00F 119.8 . . ? C00J C00F C00C 120.47(18) . . ? C00J C00F H00F 119.8 . . ? C00D C00G H00G 119.7 . . ? C00D C00G C00I 120.56(17) . . ? C00I C00G H00G 119.7 . . ? C00P C00H N003 120.15(16) . . ? C00P C00H C012 118.79(19) . . ? C012 C00H N003 121.06(19) . . ? C00G C00I N003 120.35(16) . . ? C00W C00I N003 120.66(17) . . ? C00W C00I C00G 118.93(16) . . ? C00F C00J C007 123.18(17) . . ? C00F C00J C00K 118.71(16) . . ? C00K C00J C007 118.06(16) . . ? C00J C00K H00K 119.0 . . ? C00N C00K C00J 121.90(17) . . ? C00N C00K H00K 119.0 . . ? C004 C00L H00L 119.9 . . ? C00V C00L C004 120.15(19) . . ? C00V C00L H00L 119.9 . . ? C009 C00M H00M 119.6 . . ? C00U C00M C009 120.73(18) . . ? C00U C00M H00M 119.6 . . ? C008 C00N H00N 120.2 . . ? C00K C00N C008 119.64(18) . . ? C00K C00N H00N 120.2 . . ? C00R C00O H00O 119.9 . . ? C010 C00O H00O 119.9 . . ? C010 C00O C00R 120.11(19) . . ? C00H C00P H00P 119.6 . . ? C00H C00P C00Y 120.79(18) . . ? C00Y C00P H00P 119.6 . . ? C00A C00Q H00Q 119.9 . . ? C00Z C00Q C00A 120.20(19) . . ? C00Z C00Q H00Q 119.9 . . ? C00O C00R N003 120.81(17) . . ? C00O C00R C00X 118.51(19) . . ? C00X C00R N003 120.68(18) . . ? C00B C00S H00S 120.1 . . ? C00U C00S C00B 119.87(18) . . ? C00U C00S H00S 120.1 . . ? C007 C00T H00T 119.4 . . ? C007 C00T C00W 121.27(17) . . ? C00W C00T H00T 119.4 . . ? C00M C00U H00U 120.0 . . ? C00S C00U C00M 120.07(19) . . ? C00S C00U H00U 120.0 . . ? C00L C00V H00V 119.7 . . ? C00Z C00V C00L 120.58(18) . . ? C00Z C00V H00V 119.7 . . ? C00I C00W C00T 120.17(18) . . ? C00I C00W H00W 119.9 . . ? C00T C00W H00W 119.9 . . ? C00R C00X H00X 119.7 . . ? C011 C00X C00R 120.7(2) . . ? C011 C00X H00X 119.7 . . ? C00P C00Y H00Y 120.0 . . ? C014 C00Y C00P 120.1(2) . . ? C014 C00Y H00Y 120.0 . . ? C00Q C00Z H00Z 120.2 . . ? C00V C00Z C00Q 119.59(18) . . ? C00V C00Z H00Z 120.2 . . ? C00O C010 H010 119.3 . . ? C013 C010 C00O 121.3(2) . . ? C013 C010 H010 119.3 . . ? C00X C011 H011 119.8 . . ? C013 C011 C00X 120.48(19) . . ? C013 C011 H011 119.8 . . ? C00H C012 H012 120.1 . . ? C015 C012 C00H 119.8(2) . . ? C015 C012 H012 120.1 . . ? C010 C013 H013 120.6 . . ? C011 C013 C010 118.9(2) . . ? C011 C013 H013 120.6 . . ? C00Y C014 H014 120.4 . . ? C015 C014 C00Y 119.2(2) . . ? C015 C014 H014 120.4 . . ? C012 C015 H015 119.4 . . ? C014 C015 C012 121.24(19) . . ? C014 C015 H015 119.4 . . ? 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 C006 1.321(2) . ? N001 C008 1.369(2) . ? N002 C005 1.328(2) . ? N002 C00C 1.368(2) . ? N003 C00H 1.418(2) . ? N003 C00I 1.427(2) . ? N003 C00R 1.414(3) . ? C004 C005 1.488(2) . ? C004 C00A 1.387(2) . ? C004 C00L 1.388(2) . ? C005 C006 1.438(3) . ? C006 C009 1.490(2) . ? C007 C00D 1.399(2) . ? C007 C00J 1.491(2) . ? C007 C00T 1.386(3) . ? C008 C00C 1.403(3) . ? C008 C00N 1.406(2) . ? C009 C00E 1.390(2) . ? C009 C00M 1.393(3) . ? C00A H00A 0.9300 . ? C00A C00Q 1.387(2) . ? C00B H00B 0.9300 . ? C00B C00E 1.387(2) . ? C00B C00S 1.384(3) . ? C00C C00F 1.418(2) . ? C00D H00D 0.9300 . ? C00D C00G 1.378(2) . ? C00E H00E 0.9300 . ? C00F H00F 0.9300 . ? C00F C00J 1.377(2) . ? C00G H00G 0.9300 . ? C00G C00I 1.389(3) . ? C00H C00P 1.385(3) . ? C00H C012 1.397(2) . ? C00I C00W 1.388(2) . ? C00J C00K 1.414(3) . ? C00K H00K 0.9300 . ? C00K C00N 1.368(2) . ? C00L H00L 0.9300 . ? C00L C00V 1.386(3) . ? C00M H00M 0.9300 . ? C00M C00U 1.381(2) . ? C00N H00N 0.9300 . ? C00O H00O 0.9300 . ? C00O C00R 1.388(3) . ? C00O C010 1.385(3) . ? C00P H00P 0.9300 . ? C00P C00Y 1.388(3) . ? C00Q H00Q 0.9300 . ? C00Q C00Z 1.380(3) . ? C00R C00X 1.401(3) . ? C00S H00S 0.9300 . ? C00S C00U 1.379(3) . ? C00T H00T 0.9300 . ? C00T C00W 1.389(2) . ? C00U H00U 0.9300 . ? C00V H00V 0.9300 . ? C00V C00Z 1.377(3) . ? C00W H00W 0.9300 . ? C00X H00X 0.9300 . ? C00X C011 1.386(3) . ? C00Y H00Y 0.9300 . ? C00Y C014 1.382(3) . ? C00Z H00Z 0.9300 . ? C010 H010 0.9300 . ? C010 C013 1.383(3) . ? C011 H011 0.9300 . ? C011 C013 1.380(3) . ? C012 H012 0.9300 . ? C012 C015 1.380(3) . ? C013 H013 0.9300 . ? C014 H014 0.9300 . ? C014 C015 1.378(3) . ? C015 H015 0.9300 . ? 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 C006 C009 C00E 129.86(17) . . . . ? N001 C006 C009 C00M -44.9(2) . . . . ? N001 C008 C00C N002 -4.0(3) . . . . ? N001 C008 C00C C00F 177.96(16) . . . . ? N001 C008 C00N C00K -177.37(17) . . . . ? N002 C005 C006 N001 -5.3(3) . . . . ? N002 C005 C006 C009 172.67(16) . . . . ? N002 C00C C00F C00J -178.16(16) . . . . ? N003 C00H C00P C00Y -177.21(17) . . . . ? N003 C00H C012 C015 178.81(18) . . . . ? N003 C00I C00W C00T 175.30(19) . . . . ? N003 C00R C00X C011 -178.40(17) . . . . ? C004 C005 C006 N001 173.75(15) . . . . ? C004 C005 C006 C009 -8.3(3) . . . . ? C004 C00A C00Q C00Z -0.8(3) . . . . ? C004 C00L C00V C00Z -0.9(3) . . . . ? C005 N002 C00C C008 0.6(2) . . . . ? C005 N002 C00C C00F 178.58(16) . . . . ? C005 C004 C00A C00Q 178.45(16) . . . . ? C005 C004 C00L C00V -177.55(17) . . . . ? C005 C006 C009 C00E -48.2(2) . . . . ? C005 C006 C009 C00M 137.07(18) . . . . ? C006 N001 C008 C00C 2.7(3) . . . . ? C006 N001 C008 C00N -178.09(16) . . . . ? C006 C009 C00E C00B -174.28(17) . . . . ? C006 C009 C00M C00U 175.72(17) . . . . ? C007 C00D C00G C00I -2.0(3) . . . . ? C007 C00J C00K C00N -177.76(17) . . . . ? C007 C00T C00W C00I -1.9(3) . . . . ? C008 N001 C006 C005 1.8(2) . . . . ? C008 N001 C006 C009 -176.36(15) . . . . ? C008 C00C C00F C00J -0.1(3) . . . . ? C009 C00M C00U C00S -1.6(3) . . . . ? C00A C004 C005 N002 -47.1(2) . . . . ? C00A C004 C005 C006 133.77(18) . . . . ? C00A C004 C00L C00V 0.1(3) . . . . ? C00A C00Q C00Z C00V 0.0(3) . . . . ? C00B C00S C00U C00M 0.9(3) . . . . ? C00C N002 C005 C004 -175.23(15) . . . . ? C00C N002 C005 C006 3.9(2) . . . . ? C00C C008 C00N C00K 1.9(3) . . . . ? C00C C00F C00J C007 178.24(17) . . . . ? C00C C00F C00J C00K 0.9(3) . . . . ? C00D C007 C00J C00F 144.49(18) . . . . ? C00D C007 C00J C00K -38.1(3) . . . . ? C00D C007 C00T C00W 3.7(3) . . . . ? C00D C00G C00I N003 -173.36(18) . . . . ? C00D C00G C00I C00W 3.8(3) . . . . ? C00E C009 C00M C00U 0.9(3) . . . . ? C00E C00B C00S C00U 0.5(3) . . . . ? C00F C00J C00K C00N -0.3(3) . . . . ? C00G C00I C00W C00T -1.9(3) . . . . ? C00H N003 C00I C00G 47.9(3) . . . . ? C00H N003 C00I C00W -129.2(2) . . . . ? C00H N003 C00R C00O -143.95(18) . . . . ? C00H N003 C00R C00X 35.8(3) . . . . ? C00H C00P C00Y C014 -1.6(3) . . . . ? C00H C012 C015 C014 -1.7(3) . . . . ? C00I N003 C00H C00P 35.9(3) . . . . ? C00I N003 C00H C012 -143.11(18) . . . . ? C00I N003 C00R C00O 33.8(3) . . . . ? C00I N003 C00R C00X -146.46(18) . . . . ? C00J C007 C00D C00G 173.55(18) . . . . ? C00J C007 C00T C00W -171.50(19) . . . . ? C00J C00K C00N C008 -1.1(3) . . . . ? C00L C004 C005 N002 130.50(19) . . . . ? C00L C004 C005 C006 -48.6(2) . . . . ? C00L C004 C00A C00Q 0.7(3) . . . . ? C00L C00V C00Z C00Q 0.8(3) . . . . ? C00M C009 C00E C00B 0.5(3) . . . . ? C00N C008 C00C N002 176.76(16) . . . . ? C00N C008 C00C C00F -1.3(3) . . . . ? C00O C00R C00X C011 1.3(3) . . . . ? C00O C010 C013 C011 1.3(3) . . . . ? C00P C00H C012 C015 -0.2(3) . . . . ? C00P C00Y C014 C015 -0.3(3) . . . . ? C00R N003 C00H C00P -146.26(18) . . . . ? C00R N003 C00H C012 34.7(3) . . . . ? C00R N003 C00I C00G -129.9(2) . . . . ? C00R N003 C00I C00W 52.9(3) . . . . ? C00R C00O C010 C013 -0.9(3) . . . . ? C00R C00X C011 C013 -0.9(3) . . . . ? C00S C00B C00E C009 -1.1(3) . . . . ? C00T C007 C00D C00G -1.7(3) . . . . ? C00T C007 C00J C00F -40.5(3) . . . . ? C00T C007 C00J C00K 136.9(2) . . . . ? C00X C011 C013 C010 -0.5(3) . . . . ? C00Y C014 C015 C012 1.9(3) . . . . ? C010 C00O C00R N003 179.27(17) . . . . ? C010 C00O C00R C00X -0.4(3) . . . . ? C012 C00H C00P C00Y 1.8(3) . . . . ?