#------------------------------------------------------------------------------ #$Date: 2021-07-05 21:06:10 +0300 (Mon, 05 Jul 2021) $ #$Revision: 267222 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/06/06/7060685.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_7060685 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 'C37 H26 N4' _chemical_formula_sum 'C37 H26 N4' _chemical_formula_weight 526.62 _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 _audit_creation_date 2020-07-07 _audit_creation_method ; Olex2 1.3 (compiled 2020.06.28 svn.raecde09e for OlexSys, GUI svn.r6132) ; _audit_update_record ; 2021-02-25 deposited with the CCDC. 2021-05-19 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 116.82(2) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 18.920(11) _cell_length_b 8.897(7) _cell_length_c 17.812(10) _cell_measurement_reflns_used 1027 _cell_measurement_temperature 193 _cell_measurement_theta_max 24.86 _cell_measurement_theta_min 2.61 _cell_volume 2676(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 2014/5 (Sheldrick, 2014)' _diffrn_ambient_temperature 193 _diffrn_measured_fraction_theta_full 0.967 _diffrn_measured_fraction_theta_max 0.967 _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 0.0994 _diffrn_reflns_av_unetI/netI 0.1238 _diffrn_reflns_Laue_measured_fraction_full 0.967 _diffrn_reflns_Laue_measured_fraction_max 0.967 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_h_min -17 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -21 _diffrn_reflns_number 11360 _diffrn_reflns_point_group_measured_fraction_full 0.967 _diffrn_reflns_point_group_measured_fraction_max 0.967 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 25.346 _diffrn_reflns_theta_min 2.413 _diffrn_source_current 40.0 _diffrn_source_power 2.0 _diffrn_source_voltage 50.0 _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.078 _exptl_absorpt_correction_T_max 0.7456 _exptl_absorpt_correction_T_min 0.3847 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; SADABS-2016/2 (Bruker,2016/2) was used for absorption correction. wR2(int) was 0.1726 before and 0.0937 after correction. The Ratio of minimum to maximum transmission is 0.5160. The \l/2 correction factor is Not present. ; _exptl_crystal_colour yellow _exptl_crystal_colour_primary yellow _exptl_crystal_density_diffrn 1.307 _exptl_crystal_description plate _exptl_crystal_F_000 1104 _exptl_crystal_size_max 0.1 _exptl_crystal_size_mid 0.1 _exptl_crystal_size_min 0.05 _refine_diff_density_max 0.283 _refine_diff_density_min -0.317 _refine_diff_density_rms 0.072 _refine_ls_extinction_coef 0.017(4) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method 'SHELXL-2018/3 (Sheldrick 2018)' _refine_ls_goodness_of_fit_ref 1.043 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 371 _refine_ls_number_reflns 4743 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.043 _refine_ls_R_factor_all 0.1518 _refine_ls_R_factor_gt 0.0794 _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^)+(0.1392P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.2049 _refine_ls_wR_factor_ref 0.2763 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2465 _reflns_number_total 4743 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d1nj01350e2.cif _cod_data_source_block 11_a _cod_depositor_comments 'Adding full bibliography for 7060684--7060687.cif.' _cod_database_code 7060685 _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 0.996 _shelx_estimated_absorpt_t_min 0.992 _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), C00A(H00A), C00B(H00B), C00G(H00G), C00I(H00I), C00K(H00K), C00L(H00L), C00M(H00M), C00N(H00N), C00P(H00P), C00Q(H00Q), C00R(H00R), 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 11_a.res in P2(1)/c 11_a.res created by SHELXL-2018/3 at 08:21:58 on 07-Jul-2020 CELL 0.71073 18.9203 8.897 17.8116 90 116.825 90 ZERR 4 0.0114 0.0069 0.0103 0 0.022 0 LATT 1 SYMM -X,0.5+Y,0.5-Z SFAC C H N UNIT 148 104 16 L.S. 10 PLAN 5 SIZE 0.05 0.1 0.1 TEMP -80.15 CONF BOND $H LIST 6 fmap 2 acta MORE -1 REM REM REM WGHT 0.139200 EXTI 0.016777 FVAR 0.55357 N001 3 0.334924 0.661906 0.372540 11.00000 0.04435 0.04987 = 0.03986 -0.00240 0.02539 -0.00267 N002 3 0.457017 0.657536 0.487174 11.00000 0.04138 0.05779 = 0.04031 0.00014 0.02212 0.00274 N003 3 0.261628 0.649704 0.478157 11.00000 0.04326 0.06139 = 0.04298 0.00002 0.02542 0.00014 N004 3 0.694034 0.663834 0.973439 11.00000 0.04174 0.07091 = 0.03835 -0.00279 0.02100 -0.00285 C005 1 0.257923 0.663756 0.341907 11.00000 0.04606 0.03883 = 0.03862 -0.00522 0.02526 -0.00219 C006 1 0.219658 0.663487 0.394990 11.00000 0.04719 0.04611 = 0.03860 -0.00294 0.02707 -0.00337 C007 1 0.133509 0.678987 0.364407 11.00000 0.03789 0.05421 = 0.03574 -0.00417 0.02233 0.00102 C008 1 0.212560 0.661833 0.248972 11.00000 0.04103 0.04291 = 0.03952 0.00081 0.02377 0.00431 C009 1 0.649940 0.563582 0.832746 11.00000 0.03624 0.05409 = 0.04418 -0.00065 0.01856 0.00325 AFIX 43 H009 2 0.698881 0.511673 0.851723 11.00000 -1.20000 AFIX 0 C00A 1 0.596031 0.556856 0.748939 11.00000 0.04448 0.05165 = 0.04808 -0.00010 0.02930 0.00379 AFIX 43 H00A 2 0.608823 0.502486 0.710797 11.00000 -1.20000 AFIX 0 C00B 1 0.153699 0.559243 0.208254 11.00000 0.05018 0.05167 = 0.04437 -0.00511 0.02770 -0.00175 AFIX 43 H00B 2 0.139410 0.491253 0.240237 11.00000 -1.20000 AFIX 0 C00C 1 0.634213 0.644175 0.889559 11.00000 0.04388 0.05434 = 0.03379 0.00220 0.01971 -0.00277 C00D 1 0.770924 0.697714 0.985133 11.00000 0.03987 0.06308 = 0.04119 -0.00727 0.02047 0.00055 C00E 1 0.377556 0.655139 0.457225 11.00000 0.04098 0.04235 = 0.04048 -0.00710 0.02407 -0.00324 C00F 1 0.468662 0.633106 0.629538 11.00000 0.04267 0.04486 = 0.04303 -0.00202 0.02181 0.00255 C00G 1 0.388659 0.632388 0.597446 11.00000 0.04627 0.05818 = 0.03559 0.00341 0.02556 0.00267 AFIX 43 H00G 2 0.364671 0.623601 0.633992 11.00000 -1.20000 AFIX 0 C00H 1 0.341085 0.644640 0.510060 11.00000 0.03395 0.05385 = 0.04204 -0.00326 0.02445 -0.00431 C00I 1 0.560404 0.709718 0.862051 11.00000 0.04824 0.05268 = 0.04570 -0.00134 0.02755 0.00719 AFIX 43 H00I 2 0.547210 0.760213 0.901026 11.00000 -1.20000 AFIX 0 C00J 1 0.523596 0.628224 0.719700 11.00000 0.03879 0.05159 = 0.03698 -0.00298 0.02114 -0.00233 C00K 1 0.782257 0.793758 0.931315 11.00000 0.04609 0.06397 = 0.04547 -0.00914 0.02171 -0.00158 AFIX 43 H00K 2 0.737804 0.840910 0.887327 11.00000 -1.20000 AFIX 0 C00L 1 0.499067 0.645410 0.569220 11.00000 0.03831 0.05449 = 0.04313 -0.00609 0.01981 -0.00444 AFIX 43 H00L 2 0.555034 0.644744 0.590573 11.00000 -1.20000 AFIX 0 C00M 1 0.505944 0.702254 0.778564 11.00000 0.03899 0.05692 = 0.04016 -0.00078 0.01844 0.00690 AFIX 43 H00M 2 0.455545 0.748088 0.760580 11.00000 -1.20000 AFIX 0 C00N 1 0.622877 0.539084 1.039960 11.00000 0.05297 0.05281 = 0.04557 -0.00042 0.02660 -0.00242 AFIX 43 H00N 2 0.595804 0.478890 0.991176 11.00000 -1.20000 AFIX 0 C00O 1 0.677238 0.644908 1.042519 11.00000 0.04361 0.05316 = 0.03900 0.00352 0.01996 0.00806 C00P 1 0.231334 0.762044 0.201098 11.00000 0.05967 0.06200 = 0.04719 0.00147 0.03250 -0.00381 AFIX 43 H00P 2 0.271957 0.834413 0.227997 11.00000 -1.20000 AFIX 0 C00Q 1 0.014926 0.598279 0.368907 11.00000 0.04720 0.06549 = 0.06562 -0.00310 0.03479 -0.00467 AFIX 43 H00Q 2 -0.010787 0.531887 0.390505 11.00000 -1.20000 AFIX 0 C00R 1 0.094311 0.585127 0.394570 11.00000 0.04570 0.05233 = 0.05017 0.00724 0.02737 0.00486 AFIX 43 H00R 2 0.123251 0.509438 0.434187 11.00000 -1.20000 AFIX 0 C00S 1 0.089539 0.786651 0.306417 11.00000 0.04980 0.06193 = 0.04894 0.00990 0.03071 0.01198 AFIX 43 H00S 2 0.114587 0.851173 0.283179 11.00000 -1.20000 AFIX 0 C00T 1 0.114598 0.552685 0.121357 11.00000 0.05454 0.06268 = 0.04357 -0.01026 0.02237 -0.00100 AFIX 43 H00T 2 0.075432 0.477970 0.094011 11.00000 -1.20000 AFIX 0 C00U 1 0.837259 0.635702 1.051445 11.00000 0.05549 0.06763 = 0.04922 -0.00486 0.02509 0.00603 AFIX 43 H00U 2 0.831129 0.569628 1.089999 11.00000 -1.20000 AFIX 0 C00V 1 0.716382 0.730571 1.114897 11.00000 0.05491 0.05786 = 0.04959 -0.00645 0.02761 -0.00118 AFIX 43 H00V 2 0.753026 0.805406 1.116944 11.00000 -1.20000 AFIX 0 C00W 1 0.607958 0.520920 1.108252 11.00000 0.06405 0.05340 = 0.06355 0.00528 0.04065 0.00310 AFIX 43 H00W 2 0.569480 0.449761 1.105648 11.00000 -1.20000 AFIX 0 C00X 1 0.702694 0.708276 1.183585 11.00000 0.05760 0.07389 = 0.04390 -0.00974 0.02456 0.00287 AFIX 43 H00X 2 0.731190 0.764978 1.233479 11.00000 -1.20000 AFIX 0 C00Y 1 0.856945 0.822882 0.940021 11.00000 0.05753 0.06199 = 0.07175 -0.01496 0.04138 -0.01053 AFIX 43 H00Y 2 0.863431 0.885725 0.900450 11.00000 -1.20000 AFIX 0 C00Z 1 0.132694 0.654689 0.074877 11.00000 0.06370 0.07134 = 0.03657 0.00403 0.02382 0.01825 AFIX 43 H00Z 2 0.104480 0.653927 0.015208 11.00000 -1.20000 AFIX 0 C010 1 0.911511 0.670225 1.060993 11.00000 0.04104 0.08835 = 0.05391 -0.01275 0.01693 0.01758 AFIX 43 H010 2 0.956600 0.629605 1.107228 11.00000 -1.20000 AFIX 0 C011 1 -0.028046 0.707528 0.311779 11.00000 0.04567 0.07866 = 0.06598 0.00490 0.03209 0.01126 AFIX 43 H011 2 -0.083405 0.717056 0.293503 11.00000 -1.20000 AFIX 0 C012 1 0.191248 0.756855 0.114736 11.00000 0.06751 0.07783 = 0.04746 0.00641 0.03556 -0.00113 AFIX 43 H012 2 0.204675 0.825701 0.082441 11.00000 -1.20000 AFIX 0 C013 1 0.647899 0.604173 1.180001 11.00000 0.07315 0.06671 = 0.05549 0.01069 0.04248 0.01631 AFIX 43 H013 2 0.637612 0.589713 1.227007 11.00000 -1.20000 AFIX 0 C014 1 0.921774 0.761990 1.005192 11.00000 0.04711 0.08883 = 0.07424 -0.03549 0.03515 -0.01129 AFIX 43 H014 2 0.973450 0.783141 1.011703 11.00000 -1.20000 AFIX 0 C015 1 0.010034 0.801482 0.281976 11.00000 0.06185 0.07585 = 0.06439 0.01474 0.03782 0.02500 AFIX 43 H015 2 -0.018912 0.878747 0.243558 11.00000 -1.20000 AFIX 0 HKLF 4 REM 11_a.res in P2(1)/c REM wR2 = 0.2763, GooF = S = 1.043, Restrained GooF = 1.043 for all data REM R1 = 0.0794 for 2465 Fo > 4sig(Fo) and 0.1518 for all 4743 data REM 371 parameters refined using 0 restraints END WGHT 0.1385 0.0000 REM Highest difference peak 0.283, deepest hole -0.317, 1-sigma level 0.072 Q1 1 0.3549 0.5783 0.4755 11.00000 0.05 0.28 Q2 1 0.3448 0.7017 0.4677 11.00000 0.05 0.28 Q3 1 0.5807 0.6558 0.8765 11.00000 0.05 0.26 Q4 1 0.0557 0.6570 0.2805 11.00000 0.05 0.26 Q5 1 0.2000 0.8256 0.1791 11.00000 0.05 0.25 ; _shelx_res_checksum 24265 _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 0.33492(19) 0.6619(4) 0.3725(2) 0.0423(9) Uani 1 1 d . . . . . N002 N 0.45702(19) 0.6575(4) 0.4872(2) 0.0451(9) Uani 1 1 d . . . . . N003 N 0.2616(2) 0.6497(4) 0.4782(2) 0.0470(9) Uani 1 1 d . . . . . N004 N 0.6940(2) 0.6638(4) 0.9734(2) 0.0492(10) Uani 1 1 d . . . . . C005 C 0.2579(2) 0.6638(4) 0.3419(2) 0.0388(10) Uani 1 1 d . . . . . C006 C 0.2197(2) 0.6635(5) 0.3950(2) 0.0411(10) Uani 1 1 d . . . . . C007 C 0.1335(2) 0.6790(5) 0.3644(2) 0.0405(10) Uani 1 1 d . . . . . C008 C 0.2126(2) 0.6618(4) 0.2490(2) 0.0390(10) Uani 1 1 d . . . . . C009 C 0.6499(2) 0.5636(5) 0.8327(2) 0.0447(10) Uani 1 1 d . . . . . H009 H 0.698881 0.511673 0.851723 0.054 Uiso 1 1 calc R U . . . C00A C 0.5960(2) 0.5569(5) 0.7489(3) 0.0449(10) Uani 1 1 d . . . . . H00A H 0.608823 0.502486 0.710797 0.054 Uiso 1 1 calc R U . . . C00B C 0.1537(2) 0.5592(5) 0.2083(3) 0.0463(11) Uani 1 1 d . . . . . H00B H 0.139410 0.491253 0.240237 0.056 Uiso 1 1 calc R U . . . C00C C 0.6342(2) 0.6442(5) 0.8896(2) 0.0432(10) Uani 1 1 d . . . . . C00D C 0.7709(2) 0.6977(5) 0.9851(3) 0.0472(11) Uani 1 1 d . . . . . C00E C 0.3776(2) 0.6551(4) 0.4572(2) 0.0391(10) Uani 1 1 d . . . . . C00F C 0.4687(2) 0.6331(5) 0.6295(2) 0.0426(10) Uani 1 1 d . . . . . C00G C 0.3887(2) 0.6324(5) 0.5974(2) 0.0440(10) Uani 1 1 d . . . . . H00G H 0.364671 0.623601 0.633992 0.053 Uiso 1 1 calc R U . . . C00H C 0.3411(2) 0.6446(5) 0.5101(2) 0.0405(10) Uani 1 1 d . . . . . C00I C 0.5604(2) 0.7097(5) 0.8621(3) 0.0465(11) Uani 1 1 d . . . . . H00I H 0.547210 0.760213 0.901026 0.056 Uiso 1 1 calc R U . . . C00J C 0.5236(2) 0.6282(5) 0.7197(2) 0.0409(10) Uani 1 1 d . . . . . C00K C 0.7823(3) 0.7938(5) 0.9313(3) 0.0514(11) Uani 1 1 d . . . . . H00K H 0.737804 0.840910 0.887327 0.062 Uiso 1 1 calc R U . . . C00L C 0.4991(2) 0.6454(5) 0.5692(3) 0.0448(10) Uani 1 1 d . . . . . H00L H 0.555034 0.644744 0.590573 0.054 Uiso 1 1 calc R U . . . C00M C 0.5059(2) 0.7023(5) 0.7786(2) 0.0451(11) Uani 1 1 d . . . . . H00M H 0.455545 0.748088 0.760580 0.054 Uiso 1 1 calc R U . . . C00N C 0.6229(2) 0.5391(5) 1.0400(3) 0.0488(11) Uani 1 1 d . . . . . H00N H 0.595804 0.478890 0.991176 0.059 Uiso 1 1 calc R U . . . C00O C 0.6772(2) 0.6449(5) 1.0425(3) 0.0448(10) Uani 1 1 d . . . . . C00P C 0.2313(3) 0.7620(6) 0.2011(3) 0.0531(12) Uani 1 1 d . . . . . H00P H 0.271957 0.834413 0.227997 0.064 Uiso 1 1 calc R U . . . C00Q C 0.0149(2) 0.5983(6) 0.3689(3) 0.0559(12) Uani 1 1 d . . . . . H00Q H -0.010787 0.531887 0.390505 0.067 Uiso 1 1 calc R U . . . C00R C 0.0943(2) 0.5851(5) 0.3946(3) 0.0472(11) Uani 1 1 d . . . . . H00R H 0.123251 0.509438 0.434187 0.057 Uiso 1 1 calc R U . . . C00S C 0.0895(2) 0.7867(5) 0.3064(3) 0.0504(11) Uani 1 1 d . . . . . H00S H 0.114587 0.851173 0.283179 0.060 Uiso 1 1 calc R U . . . C00T C 0.1146(3) 0.5527(5) 0.1214(3) 0.0535(12) Uani 1 1 d . . . . . H00T H 0.075432 0.477970 0.094011 0.064 Uiso 1 1 calc R U . . . C00U C 0.8373(3) 0.6357(6) 1.0514(3) 0.0569(12) Uani 1 1 d . . . . . H00U H 0.831129 0.569628 1.089999 0.068 Uiso 1 1 calc R U . . . C00V C 0.7164(3) 0.7306(5) 1.1149(3) 0.0526(12) Uani 1 1 d . . . . . H00V H 0.753026 0.805406 1.116944 0.063 Uiso 1 1 calc R U . . . C00W C 0.6080(3) 0.5209(5) 1.1083(3) 0.0559(12) Uani 1 1 d . . . . . H00W H 0.569480 0.449761 1.105648 0.067 Uiso 1 1 calc R U . . . C00X C 0.7027(3) 0.7083(6) 1.1836(3) 0.0578(13) Uani 1 1 d . . . . . H00X H 0.731190 0.764978 1.233479 0.069 Uiso 1 1 calc R U . . . C00Y C 0.8569(3) 0.8229(6) 0.9400(3) 0.0591(13) Uani 1 1 d . . . . . H00Y H 0.863431 0.885725 0.900450 0.071 Uiso 1 1 calc R U . . . C00Z C 0.1327(3) 0.6547(6) 0.0749(3) 0.0568(13) Uani 1 1 d . . . . . H00Z H 0.104480 0.653927 0.015208 0.068 Uiso 1 1 calc R U . . . C010 C 0.9115(3) 0.6702(6) 1.0610(3) 0.0628(14) Uani 1 1 d . . . . . H010 H 0.956600 0.629605 1.107228 0.075 Uiso 1 1 calc R U . . . C011 C -0.0280(3) 0.7075(6) 0.3118(3) 0.0608(13) Uani 1 1 d . . . . . H011 H -0.083405 0.717056 0.293503 0.073 Uiso 1 1 calc R U . . . C012 C 0.1912(3) 0.7569(6) 0.1147(3) 0.0606(13) Uani 1 1 d . . . . . H012 H 0.204675 0.825701 0.082441 0.073 Uiso 1 1 calc R U . . . C013 C 0.6479(3) 0.6042(6) 1.1800(3) 0.0600(13) Uani 1 1 d . . . . . H013 H 0.637612 0.589713 1.227007 0.072 Uiso 1 1 calc R U . . . C014 C 0.9218(3) 0.7620(6) 1.0052(3) 0.0671(15) Uani 1 1 d . . . . . H014 H 0.973450 0.783141 1.011703 0.081 Uiso 1 1 calc R U . . . C015 C 0.0100(3) 0.8015(6) 0.2820(3) 0.0638(14) Uani 1 1 d . . . . . H015 H -0.018912 0.878747 0.243558 0.077 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 0.044(2) 0.050(2) 0.040(2) -0.0024(15) 0.0254(17) -0.0027(16) N002 0.041(2) 0.058(2) 0.040(2) 0.0001(16) 0.0221(16) 0.0027(17) N003 0.043(2) 0.061(2) 0.043(2) 0.0000(16) 0.0254(17) 0.0001(17) N004 0.042(2) 0.071(3) 0.038(2) -0.0028(17) 0.0210(16) -0.0029(18) C005 0.046(2) 0.039(2) 0.039(2) -0.0052(17) 0.0253(19) -0.0022(18) C006 0.047(2) 0.046(3) 0.039(2) -0.0029(17) 0.027(2) -0.0034(19) C007 0.038(2) 0.054(3) 0.036(2) -0.0042(18) 0.0223(18) 0.0010(19) C008 0.041(2) 0.043(2) 0.040(2) 0.0008(17) 0.0238(18) 0.0043(19) C009 0.036(2) 0.054(3) 0.044(3) -0.0006(19) 0.0186(19) 0.0032(19) C00A 0.044(2) 0.052(3) 0.048(3) -0.0001(19) 0.029(2) 0.004(2) C00B 0.050(2) 0.052(3) 0.044(3) -0.0051(19) 0.028(2) -0.002(2) C00C 0.044(2) 0.054(3) 0.034(2) 0.0022(18) 0.0197(19) -0.003(2) C00D 0.040(2) 0.063(3) 0.041(2) -0.007(2) 0.020(2) 0.001(2) C00E 0.041(2) 0.042(3) 0.040(2) -0.0071(17) 0.0241(19) -0.0032(18) C00F 0.043(2) 0.045(3) 0.043(2) -0.0020(18) 0.0218(19) 0.0025(19) C00G 0.046(2) 0.058(3) 0.036(2) 0.0034(19) 0.026(2) 0.003(2) C00H 0.034(2) 0.054(3) 0.042(2) -0.0033(18) 0.0244(18) -0.0043(18) C00I 0.048(2) 0.053(3) 0.046(3) -0.0013(19) 0.028(2) 0.007(2) C00J 0.039(2) 0.052(3) 0.037(2) -0.0030(18) 0.0211(18) -0.0023(19) C00K 0.046(3) 0.064(3) 0.045(3) -0.009(2) 0.022(2) -0.002(2) C00L 0.038(2) 0.054(3) 0.043(3) -0.0061(19) 0.020(2) -0.0044(19) C00M 0.039(2) 0.057(3) 0.040(3) -0.0008(19) 0.018(2) 0.007(2) C00N 0.053(3) 0.053(3) 0.046(3) -0.0004(19) 0.027(2) -0.002(2) C00O 0.044(2) 0.053(3) 0.039(2) 0.0035(19) 0.0200(19) 0.008(2) C00P 0.060(3) 0.062(3) 0.047(3) 0.001(2) 0.033(2) -0.004(2) C00Q 0.047(3) 0.065(3) 0.066(3) -0.003(2) 0.035(2) -0.005(2) C00R 0.046(2) 0.052(3) 0.050(3) 0.007(2) 0.027(2) 0.005(2) C00S 0.050(3) 0.062(3) 0.049(3) 0.010(2) 0.031(2) 0.012(2) C00T 0.055(3) 0.063(3) 0.044(3) -0.010(2) 0.022(2) -0.001(2) C00U 0.055(3) 0.068(3) 0.049(3) -0.005(2) 0.025(2) 0.006(2) C00V 0.055(3) 0.058(3) 0.050(3) -0.006(2) 0.028(2) -0.001(2) C00W 0.064(3) 0.053(3) 0.064(3) 0.005(2) 0.041(3) 0.003(2) C00X 0.058(3) 0.074(4) 0.044(3) -0.010(2) 0.025(2) 0.003(3) C00Y 0.058(3) 0.062(3) 0.072(3) -0.015(2) 0.041(3) -0.011(2) C00Z 0.064(3) 0.071(4) 0.037(3) 0.004(2) 0.024(2) 0.018(3) C010 0.041(3) 0.088(4) 0.054(3) -0.013(3) 0.017(2) 0.018(3) C011 0.046(3) 0.079(4) 0.066(3) 0.005(3) 0.032(2) 0.011(3) C012 0.068(3) 0.078(4) 0.047(3) 0.006(2) 0.036(2) -0.001(3) C013 0.073(3) 0.067(3) 0.055(3) 0.011(2) 0.042(3) 0.016(3) C014 0.047(3) 0.089(4) 0.074(4) -0.035(3) 0.035(3) -0.011(3) C015 0.062(3) 0.076(4) 0.064(3) 0.015(2) 0.038(3) 0.025(3) 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 C00E 117.3(3) . . ? C00L N002 C00E 116.4(3) . . ? C006 N003 C00H 117.6(3) . . ? C00D N004 C00C 117.5(3) . . ? C00D N004 C00O 121.4(3) . . ? C00O N004 C00C 121.0(3) . . ? N001 C005 C006 121.8(4) . . ? N001 C005 C008 116.2(3) . . ? C006 C005 C008 121.9(3) . . ? N003 C006 C005 120.7(4) . . ? N003 C006 C007 115.1(3) . . ? C005 C006 C007 124.2(3) . . ? C00R C007 C006 120.0(4) . . ? C00R C007 C00S 117.7(4) . . ? C00S C007 C006 122.3(4) . . ? C00B C008 C005 121.5(4) . . ? C00B C008 C00P 118.5(4) . . ? C00P C008 C005 120.0(4) . . ? C00A C009 H009 119.4 . . ? C00A C009 C00C 121.2(4) . . ? C00C C009 H009 119.4 . . ? C009 C00A H00A 119.6 . . ? C009 C00A C00J 120.8(4) . . ? C00J C00A H00A 119.6 . . ? C008 C00B H00B 119.4 . . ? C008 C00B C00T 121.2(4) . . ? C00T C00B H00B 119.4 . . ? C009 C00C N004 120.2(4) . . ? C009 C00C C00I 118.5(4) . . ? C00I C00C N004 121.2(4) . . ? C00K C00D N004 120.5(4) . . ? C00K C00D C00U 118.3(4) . . ? C00U C00D N004 121.1(4) . . ? N001 C00E C00H 121.7(3) . . ? N002 C00E N001 115.9(3) . . ? N002 C00E C00H 122.3(4) . . ? C00G C00F C00J 124.5(4) . . ? C00G C00F C00L 115.7(4) . . ? C00L C00F C00J 119.8(4) . . ? C00F C00G H00G 120.0 . . ? C00F C00G C00H 120.1(4) . . ? C00H C00G H00G 120.0 . . ? N003 C00H C00E 120.6(4) . . ? N003 C00H C00G 120.3(3) . . ? C00E C00H C00G 119.1(3) . . ? C00C C00I H00I 119.8 . . ? C00M C00I C00C 120.4(4) . . ? C00M C00I H00I 119.8 . . ? C00A C00J C00F 121.2(4) . . ? C00A C00J C00M 117.7(4) . . ? C00M C00J C00F 121.0(4) . . ? C00D C00K H00K 119.5 . . ? C00D C00K C00Y 121.0(5) . . ? C00Y C00K H00K 119.5 . . ? N002 C00L C00F 126.3(4) . . ? N002 C00L H00L 116.8 . . ? C00F C00L H00L 116.8 . . ? C00I C00M C00J 121.1(4) . . ? C00I C00M H00M 119.5 . . ? C00J C00M H00M 119.5 . . ? C00O C00N H00N 120.1 . . ? C00W C00N H00N 120.1 . . ? C00W C00N C00O 119.9(4) . . ? C00N C00O N004 120.6(4) . . ? C00N C00O C00V 118.8(4) . . ? C00V C00O N004 120.5(4) . . ? C008 C00P H00P 120.0 . . ? C012 C00P C008 120.1(5) . . ? C012 C00P H00P 120.0 . . ? C00R C00Q H00Q 119.9 . . ? C00R C00Q C011 120.2(4) . . ? C011 C00Q H00Q 119.9 . . ? C007 C00R H00R 119.2 . . ? C00Q C00R C007 121.5(4) . . ? C00Q C00R H00R 119.2 . . ? C007 C00S H00S 119.7 . . ? C015 C00S C007 120.6(4) . . ? C015 C00S H00S 119.7 . . ? C00B C00T H00T 120.2 . . ? C00Z C00T C00B 119.6(5) . . ? C00Z C00T H00T 120.2 . . ? C00D C00U H00U 120.1 . . ? C010 C00U C00D 119.8(5) . . ? C010 C00U H00U 120.1 . . ? C00O C00V H00V 119.6 . . ? C00X C00V C00O 120.7(5) . . ? C00X C00V H00V 119.6 . . ? C00N C00W H00W 119.6 . . ? C013 C00W C00N 120.9(5) . . ? C013 C00W H00W 119.6 . . ? C00V C00X H00X 120.0 . . ? C013 C00X C00V 119.9(4) . . ? C013 C00X H00X 120.0 . . ? C00K C00Y H00Y 119.8 . . ? C014 C00Y C00K 120.3(5) . . ? C014 C00Y H00Y 119.8 . . ? C00T C00Z H00Z 120.2 . . ? C012 C00Z C00T 119.6(4) . . ? C012 C00Z H00Z 120.2 . . ? C00U C010 H010 119.4 . . ? C014 C010 C00U 121.2(5) . . ? C014 C010 H010 119.4 . . ? C00Q C011 H011 120.6 . . ? C015 C011 C00Q 118.9(4) . . ? C015 C011 H011 120.6 . . ? C00P C012 H012 119.5 . . ? C00Z C012 C00P 121.0(5) . . ? C00Z C012 H012 119.5 . . ? C00W C013 H013 120.1 . . ? C00X C013 C00W 119.7(4) . . ? C00X C013 H013 120.1 . . ? C00Y C014 C010 119.2(5) . . ? C00Y C014 H014 120.4 . . ? C010 C014 H014 120.4 . . ? C00S C015 H015 119.5 . . ? C011 C015 C00S 121.1(5) . . ? C011 C015 H015 119.5 . . ? 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 N001 C005 1.305(5) . ? N001 C00E 1.353(5) . ? N002 C00E 1.350(5) . ? N002 C00L 1.316(5) . ? N003 C006 1.334(5) . ? N003 C00H 1.347(5) . ? N004 C00C 1.420(5) . ? N004 C00D 1.406(5) . ? N004 C00O 1.413(5) . ? C005 C006 1.427(5) . ? C005 C008 1.481(5) . ? C006 C007 1.473(5) . ? C007 C00R 1.377(6) . ? C007 C00S 1.379(6) . ? C008 C00B 1.368(6) . ? C008 C00P 1.386(6) . ? C009 H009 0.9500 . ? C009 C00A 1.378(5) . ? C009 C00C 1.378(6) . ? C00A H00A 0.9500 . ? C00A C00J 1.381(5) . ? C00B H00B 0.9500 . ? C00B C00T 1.383(6) . ? C00C C00I 1.383(6) . ? C00D C00K 1.371(6) . ? C00D C00U 1.392(6) . ? C00E C00H 1.399(5) . ? C00F C00G 1.355(6) . ? C00F C00J 1.468(5) . ? C00F C00L 1.434(5) . ? C00G H00G 0.9500 . ? C00G C00H 1.407(5) . ? C00I H00I 0.9500 . ? C00I C00M 1.376(5) . ? C00J C00M 1.400(5) . ? C00K H00K 0.9500 . ? C00K C00Y 1.375(6) . ? C00L H00L 0.9500 . ? C00M H00M 0.9500 . ? C00N H00N 0.9500 . ? C00N C00O 1.380(6) . ? C00N C00W 1.377(6) . ? C00O C00V 1.389(6) . ? C00P H00P 0.9500 . ? C00P C012 1.375(6) . ? C00Q H00Q 0.9500 . ? C00Q C00R 1.363(6) . ? C00Q C011 1.376(6) . ? C00R H00R 0.9500 . ? C00S H00S 0.9500 . ? C00S C015 1.371(6) . ? C00T H00T 0.9500 . ? C00T C00Z 1.372(7) . ? C00U H00U 0.9500 . ? C00U C010 1.372(6) . ? C00V H00V 0.9500 . ? C00V C00X 1.374(6) . ? C00W H00W 0.9500 . ? C00W C013 1.372(7) . ? C00X H00X 0.9500 . ? C00X C013 1.370(7) . ? C00Y H00Y 0.9500 . ? C00Y C014 1.364(7) . ? C00Z H00Z 0.9500 . ? C00Z C012 1.359(7) . ? C010 H010 0.9500 . ? C010 C014 1.366(8) . ? C011 H011 0.9500 . ? C011 C015 1.358(7) . ? C012 H012 0.9500 . ? C013 H013 0.9500 . ? 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 N003 -5.2(6) . . . . ? N001 C005 C006 C007 174.3(4) . . . . ? N001 C005 C008 C00B 128.0(4) . . . . ? N001 C005 C008 C00P -49.7(6) . . . . ? N001 C00E C00H N003 -3.9(6) . . . . ? N001 C00E C00H C00G 177.7(4) . . . . ? N002 C00E C00H N003 176.8(4) . . . . ? N002 C00E C00H C00G -1.6(6) . . . . ? N003 C006 C007 C00R -45.9(6) . . . . ? N003 C006 C007 C00S 133.3(4) . . . . ? N004 C00C C00I C00M 173.4(4) . . . . ? N004 C00D C00K C00Y -177.3(4) . . . . ? N004 C00D C00U C010 179.7(4) . . . . ? N004 C00O C00V C00X -177.3(4) . . . . ? C005 N001 C00E N002 -178.3(4) . . . . ? C005 N001 C00E C00H 2.4(6) . . . . ? C005 C006 C007 C00R 134.5(4) . . . . ? C005 C006 C007 C00S -46.2(6) . . . . ? C005 C008 C00B C00T -176.4(4) . . . . ? C005 C008 C00P C012 177.6(4) . . . . ? C006 N003 C00H C00E 0.6(6) . . . . ? C006 N003 C00H C00G 179.1(4) . . . . ? C006 C005 C008 C00B -50.4(5) . . . . ? C006 C005 C008 C00P 132.0(4) . . . . ? C006 C007 C00R C00Q 178.7(4) . . . . ? C006 C007 C00S C015 -177.4(4) . . . . ? C007 C00S C015 C011 -2.4(8) . . . . ? C008 C005 C006 N003 173.1(4) . . . . ? C008 C005 C006 C007 -7.4(6) . . . . ? C008 C00B C00T C00Z -2.7(7) . . . . ? C008 C00P C012 C00Z 0.3(7) . . . . ? C009 C00A C00J C00F 174.5(4) . . . . ? C009 C00A C00J C00M -2.4(6) . . . . ? C009 C00C C00I C00M -4.1(6) . . . . ? C00A C009 C00C N004 -172.7(4) . . . . ? C00A C009 C00C C00I 4.7(6) . . . . ? C00A C00J C00M C00I 3.0(6) . . . . ? C00B C008 C00P C012 -0.1(7) . . . . ? C00B C00T C00Z C012 2.9(7) . . . . ? C00C N004 C00D C00K 39.3(6) . . . . ? C00C N004 C00D C00U -141.0(4) . . . . ? C00C N004 C00O C00N 34.2(6) . . . . ? C00C N004 C00O C00V -147.1(4) . . . . ? C00C C009 C00A C00J -1.5(6) . . . . ? C00C C00I C00M C00J 0.2(7) . . . . ? C00D N004 C00C C009 42.6(6) . . . . ? C00D N004 C00C C00I -134.8(4) . . . . ? C00D N004 C00O C00N -143.7(4) . . . . ? C00D N004 C00O C00V 35.1(6) . . . . ? C00D C00K C00Y C014 -3.2(7) . . . . ? C00D C00U C010 C014 -1.6(7) . . . . ? C00E N001 C005 C006 1.9(6) . . . . ? C00E N001 C005 C008 -176.4(3) . . . . ? C00E N002 C00L C00F -1.4(6) . . . . ? C00F C00G C00H N003 -177.5(4) . . . . ? C00F C00G C00H C00E 1.0(6) . . . . ? C00F C00J C00M C00I -173.9(4) . . . . ? C00G C00F C00J C00A 147.2(4) . . . . ? C00G C00F C00J C00M -36.0(7) . . . . ? C00G C00F C00L N002 0.8(6) . . . . ? C00H N003 C006 C005 3.6(6) . . . . ? C00H N003 C006 C007 -175.9(4) . . . . ? C00J C00F C00G C00H 176.9(4) . . . . ? C00J C00F C00L N002 -176.8(4) . . . . ? C00K C00D C00U C010 -0.6(7) . . . . ? C00K C00Y C014 C010 0.9(7) . . . . ? C00L N002 C00E N001 -177.6(4) . . . . ? C00L N002 C00E C00H 1.7(6) . . . . ? C00L C00F C00G C00H -0.6(6) . . . . ? C00L C00F C00J C00A -35.4(6) . . . . ? C00L C00F C00J C00M 141.4(4) . . . . ? C00N C00O C00V C00X 1.5(6) . . . . ? C00N C00W C013 C00X 0.8(7) . . . . ? C00O N004 C00C C009 -135.3(4) . . . . ? C00O N004 C00C C00I 47.3(6) . . . . ? C00O N004 C00D C00K -142.8(4) . . . . ? C00O N004 C00D C00U 36.8(6) . . . . ? C00O C00N C00W C013 -1.6(7) . . . . ? C00O C00V C00X C013 -2.3(7) . . . . ? C00P C008 C00B C00T 1.3(6) . . . . ? C00Q C011 C015 C00S 1.5(8) . . . . ? C00R C007 C00S C015 1.8(7) . . . . ? C00R C00Q C011 C015 -0.2(8) . . . . ? C00S C007 C00R C00Q -0.6(7) . . . . ? C00T C00Z C012 C00P -1.7(7) . . . . ? C00U C00D C00K C00Y 3.0(7) . . . . ? C00U C010 C014 C00Y 1.5(8) . . . . ? C00V C00X C013 C00W 1.1(7) . . . . ? C00W C00N C00O N004 179.2(4) . . . . ? C00W C00N C00O C00V 0.5(6) . . . . ? C011 C00Q C00R C007 -0.2(7) . . . . ?