#------------------------------------------------------------------------------ #$Date: 2021-09-29 03:38:28 +0300 (Wed, 29 Sep 2021) $ #$Revision: 269356 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/06/09/7060971.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_7060971 loop_ _publ_author_name 'Zhou, Yuan' 'Liu, Tingting' 'Zheng, Shuang' 'Wang, Xinyuan' 'Zhang, Mei' 'Majeed, Irfan' 'Zhang, Yuanyuan' 'Wang, Hui' 'Zeng, Zhuo' _publ_section_title ; A high selection visually paper detector for hydrazine and MCL luminogens based on fluorinated-pyrrole functionalized triphenylamine ; _journal_name_full 'New Journal of Chemistry' _journal_paper_doi 10.1039/D1NJ03642D _journal_year 2021 _chemical_formula_moiety 'C29 H22 N2 O' _chemical_formula_sum 'C29 H22 N2 O' _chemical_formula_weight 414.48 _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -1' _atom_sites_solution_hydrogens geom _audit_creation_date 2018-05-03 _audit_creation_method ; Olex2 1.2 (compiled 2017.08.10 svn.r3458 for OlexSys, GUI svn.r5381) ; _audit_update_record ; 2021-06-22 deposited with the CCDC. 2021-09-23 downloaded from the CCDC. ; _cell_angle_alpha 101.526(4) _cell_angle_beta 90.300(4) _cell_angle_gamma 109.404(4) _cell_formula_units_Z 2 _cell_length_a 7.7989(4) _cell_length_b 9.2736(4) _cell_length_c 15.9266(8) _cell_measurement_reflns_used 4106 _cell_measurement_temperature 149.99(10) _cell_measurement_theta_max 73.4480 _cell_measurement_theta_min 5.1530 _cell_volume 1061.34(9) _computing_cell_refinement 'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)' _computing_data_collection 'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)' _computing_data_reduction 'CrysAlisPro 1.171.38.43 (Rigaku OD, 2015)' _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2015)' _diffrn_ambient_environment N~2~ _diffrn_ambient_temperature 149.99(10) _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 5.2913 _diffrn_detector_type AtlasS2 _diffrn_measured_fraction_theta_full 0.984 _diffrn_measured_fraction_theta_max 0.946 _diffrn_measurement_details ; List of Runs (angles in degrees, time in seconds): # Type Start End Width t~exp~ \w \q \k \f Frames #-------------------------------------------------------------------------- 1 \w -24.00 74.00 1.00 1.90 -- 40.84 -77.00 -90.00 98 2 \w 49.00 138.00 1.00 7.60 -- 108.22 -61.00-180.00 89 3 \w 83.00 122.00 1.00 7.60 -- 108.22-125.00-120.00 39 4 \w 37.00 119.00 1.00 7.60 -- 108.22-125.00 30.00 82 5 \w 36.00 75.00 1.00 7.60 -- 108.22-125.00-120.00 39 6 \w 78.00 172.00 1.00 7.60 -- 108.22 30.00 -90.00 94 7 \w 99.00 143.00 1.00 7.60 -- 108.22 125.00-180.00 44 8 \w 106.00 176.00 1.00 7.60 -- 108.22 125.00-150.00 70 9 \w 101.00 177.00 1.00 7.60 -- 108.22 125.00 -90.00 76 10 \w 80.00 174.00 1.00 7.60 -- 108.22 30.00 0.00 94 11 \w 115.00 157.00 1.00 7.60 -- 108.22 125.00 150.00 42 12 \w -113.00 -12.00 1.00 1.90 -- -40.84 -57.00 30.00 101 13 \w -112.00 -16.00 1.00 1.90 -- -40.84 -57.00 150.00 96 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, AtlasS2' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 -0.0993793000 _diffrn_orient_matrix_UB_12 0.0334030000 _diffrn_orient_matrix_UB_13 -0.0737912000 _diffrn_orient_matrix_UB_21 -0.0056075000 _diffrn_orient_matrix_UB_22 0.1513074000 _diffrn_orient_matrix_UB_23 0.0592499000 _diffrn_orient_matrix_UB_31 0.1849829000 _diffrn_orient_matrix_UB_32 0.0921718000 _diffrn_orient_matrix_UB_33 -0.0291332000 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0217 _diffrn_reflns_av_unetI/netI 0.0285 _diffrn_reflns_Laue_measured_fraction_full 0.984 _diffrn_reflns_Laue_measured_fraction_max 0.946 _diffrn_reflns_limit_h_max 9 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 19 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_number 6113 _diffrn_reflns_point_group_measured_fraction_full 0.984 _diffrn_reflns_point_group_measured_fraction_max 0.946 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 73.640 _diffrn_reflns_theta_min 5.176 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'SuperNova (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 0.616 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.92117 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.38.43 (Rigaku Oxford Diffraction, 2015) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.297 _exptl_crystal_description block _exptl_crystal_F_000 436 _exptl_crystal_size_max 0.260 _exptl_crystal_size_mid 0.180 _exptl_crystal_size_min 0.100 _refine_diff_density_max 0.206 _refine_diff_density_min -0.234 _refine_diff_density_rms 0.047 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.032 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 289 _refine_ls_number_reflns 4066 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.032 _refine_ls_R_factor_all 0.0451 _refine_ls_R_factor_gt 0.0415 _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^)+(0.0662P)^2^+0.2401P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1121 _refine_ls_wR_factor_ref 0.1164 _reflns_Friedel_coverage 0.000 _reflns_number_gt 3687 _reflns_number_total 4066 _reflns_threshold_expression 'I > 2\s(I)' _iucr_refine_instructions_details ; 18050301.res created by SHELXL-2014/7 TITL 18050301_a.res in P-1 REM Old TITL 18050301 in P-1 #2 REM SHELXT solution in P-1 REM R1 0.108, Rweak 0.005, Alpha 0.037, Orientation as input REM Formula found by SHELXT: C29 N2 O CELL 1.54184 7.7989 9.2736 15.9266 101.526 90.3 109.404 ZERR 2 0.0004 0.0004 0.0008 0.004 0.004 0.004 LATT 1 SFAC C H N O UNIT 58 44 4 2 L.S. 14 PLAN 15 BOND $H LIST 6 MORE -1 CONF fmap 2 ACTA REM REM REM WGHT 0.066200 0.240100 FVAR 0.69542 O32 4 0.246692 0.234264 0.357996 11.00000 0.03421 0.04338 = 0.03326 0.00277 0.00533 0.01088 N26 3 -0.041849 0.248315 0.483854 11.00000 0.02540 0.02296 = 0.02553 0.00505 0.00144 0.00928 N7 3 1.019361 0.278637 0.844297 11.00000 0.02510 0.02435 = 0.03247 0.00647 -0.00357 0.00661 C23 1 0.106176 0.255984 0.540136 11.00000 0.02643 0.02353 = 0.02049 0.00296 0.00251 0.01120 C4 1 0.553978 0.272250 0.702185 11.00000 0.02199 0.02488 = 0.02258 0.00614 0.00442 0.00724 C1 1 0.864330 0.274594 0.797408 11.00000 0.02225 0.02663 = 0.02386 0.00693 0.00310 0.00832 C20 1 0.396802 0.269587 0.648443 11.00000 0.02562 0.02217 = 0.02079 0.00275 0.00313 0.00870 C25 1 0.413275 0.386716 0.602505 11.00000 0.02512 0.02076 = 0.02479 0.00404 0.00285 0.00418 AFIX 43 H25 2 0.522085 0.470549 0.608436 11.00000 -1.20000 AFIX 0 C30 1 -0.038118 0.261169 0.398455 11.00000 0.03195 0.01953 = 0.02571 0.00630 -0.00251 0.00666 C8 1 1.045521 0.142118 0.861186 11.00000 0.02523 0.02628 = 0.02126 0.00531 -0.00041 0.00898 C24 1 0.269990 0.379608 0.548376 11.00000 0.03119 0.02088 = 0.02290 0.00617 0.00377 0.00887 AFIX 43 H24 2 0.283359 0.457463 0.517573 11.00000 -1.20000 AFIX 0 C2 1 0.825383 0.412523 0.799078 11.00000 0.02461 0.02235 = 0.02609 0.00097 -0.00017 0.00568 AFIX 43 H2 2 0.901898 0.506505 0.832515 11.00000 -1.20000 AFIX 0 C22 1 0.083790 0.141575 0.587589 11.00000 0.02383 0.02192 = 0.02352 0.00444 0.00303 0.00535 AFIX 43 H22 2 -0.027525 0.061142 0.583809 11.00000 -1.20000 AFIX 0 C5 1 0.592240 0.134867 0.701615 11.00000 0.02602 0.02190 = 0.02476 0.00347 0.00041 0.00476 AFIX 43 H5 2 0.512708 0.040401 0.670020 11.00000 -1.20000 AFIX 0 C3 1 0.674962 0.410927 0.751775 11.00000 0.02537 0.02174 = 0.02712 0.00487 0.00341 0.00919 AFIX 43 H3 2 0.654109 0.504410 0.753089 11.00000 -1.20000 AFIX 0 C6 1 0.744659 0.135308 0.746589 11.00000 0.02895 0.02259 = 0.02711 0.00594 0.00209 0.00964 AFIX 43 H6 2 0.768044 0.042352 0.743105 11.00000 -1.20000 AFIX 0 C9 1 1.218448 0.128907 0.856044 11.00000 0.02414 0.02912 = 0.02541 0.00569 0.00169 0.00666 AFIX 43 H9 2 1.314313 0.208686 0.841325 11.00000 -1.20000 AFIX 0 C19 1 1.257471 0.510062 0.815072 11.00000 0.02868 0.02987 = 0.03001 0.00637 0.00526 0.01384 AFIX 43 H19 2 1.225235 0.473425 0.756430 11.00000 -1.20000 AFIX 0 C21 1 0.229007 0.148324 0.640709 11.00000 0.02802 0.02183 = 0.02316 0.00701 0.00311 0.00814 AFIX 43 H21 2 0.214548 0.070714 0.671795 11.00000 -1.20000 AFIX 0 C14 1 1.164495 0.424768 0.873198 11.00000 0.02228 0.02430 = 0.03181 0.00521 -0.00006 0.00960 C11 1 1.106246 -0.123112 0.894052 11.00000 0.03354 0.02830 = 0.02998 0.00647 0.00060 0.01376 AFIX 43 H11 2 1.125987 -0.211710 0.904503 11.00000 -1.20000 AFIX 0 C10 1 1.248441 -0.002529 0.872748 11.00000 0.02638 0.03323 = 0.02987 0.00359 0.00149 0.01411 AFIX 43 H10 2 1.364436 -0.009782 0.869642 11.00000 -1.20000 AFIX 0 C13 1 0.903967 0.021706 0.884134 11.00000 0.02476 0.03336 = 0.02862 0.00932 0.00331 0.01166 AFIX 43 H13 2 0.788577 0.029787 0.889100 11.00000 -1.20000 AFIX 0 C15 1 1.212903 0.480329 0.960830 11.00000 0.02834 0.03442 = 0.03030 0.00860 0.00018 0.00914 AFIX 43 H15 2 1.150549 0.423242 0.999779 11.00000 -1.20000 AFIX 0 C12 1 0.934790 -0.110038 0.899566 11.00000 0.02902 0.03114 = 0.03215 0.01117 0.00392 0.00807 AFIX 43 H12 2 0.839063 -0.190529 0.913788 11.00000 -1.20000 AFIX 0 C31 1 0.103873 0.253778 0.342188 11.00000 0.03646 0.02732 = 0.02471 0.00674 0.00071 0.00268 AFIX 43 H31 2 0.084169 0.265372 0.286658 11.00000 -1.20000 AFIX 0 C27 1 -0.212498 0.234502 0.508671 11.00000 0.02895 0.03080 = 0.03338 0.00444 0.00488 0.01288 AFIX 43 H27 2 -0.250375 0.224525 0.563137 11.00000 -1.20000 AFIX 0 C18 1 1.399140 0.650645 0.844968 11.00000 0.02497 0.03101 = 0.04482 0.01228 0.01002 0.01189 AFIX 43 H18 2 1.461978 0.707691 0.806106 11.00000 -1.20000 AFIX 0 C29 1 -0.210906 0.254888 0.371994 11.00000 0.03721 0.02271 = 0.03476 0.00534 -0.00928 0.00984 AFIX 43 H29 2 -0.247529 0.261166 0.317571 11.00000 -1.20000 AFIX 0 C17 1 1.447254 0.706276 0.932518 11.00000 0.02117 0.02805 = 0.04876 0.00256 -0.00099 0.00674 AFIX 43 H17 2 1.541653 0.800534 0.952219 11.00000 -1.20000 AFIX 0 C28 1 -0.320141 0.237573 0.440863 11.00000 0.02778 0.02621 = 0.04425 0.00039 -0.00436 0.01222 AFIX 43 H28 2 -0.442188 0.229637 0.440925 11.00000 -1.20000 AFIX 0 C16 1 1.354323 0.621046 0.990351 11.00000 0.02992 0.03716 = 0.03540 0.00107 -0.00453 0.00965 AFIX 43 H16 2 1.386484 0.657913 1.048988 11.00000 -1.20000 AFIX 0 HKLF 4 REM 18050301_a.res in P-1 REM R1 = 0.0415 for 3687 Fo > 4sig(Fo) and 0.0451 for all 4066 data REM 289 parameters refined using 0 restraints END WGHT 0.0662 0.2401 REM Highest difference peak 0.206, deepest hole -0.234, 1-sigma level 0.047 Q1 1 0.4871 0.2738 0.6793 11.00000 0.05 0.21 Q2 1 0.3913 0.3422 0.6397 11.00000 0.05 0.20 Q3 1 1.1418 0.1653 0.8838 11.00000 0.05 0.20 Q4 1 0.5952 0.2133 0.6815 11.00000 0.05 0.19 Q5 1 -0.0251 0.2647 0.4396 11.00000 0.05 0.19 Q6 1 0.5447 0.2035 0.7223 11.00000 0.05 0.19 Q7 1 0.3163 0.2036 0.6374 11.00000 0.05 0.19 Q8 1 1.1123 0.1084 0.8295 11.00000 0.05 0.18 Q9 1 -0.1077 0.2963 0.3848 11.00000 0.05 0.18 Q10 1 0.8293 0.3436 0.8131 11.00000 0.05 0.18 Q11 1 0.1982 0.3031 0.5288 11.00000 0.05 0.18 Q12 1 0.7945 0.4235 0.7542 11.00000 0.05 0.18 Q13 1 0.1178 0.1779 0.5429 11.00000 0.05 0.18 Q14 1 1.2296 0.0777 0.8856 11.00000 0.05 0.17 Q15 1 0.8517 0.3441 0.7890 11.00000 0.05 0.17 REM The information below was added by Olex2. REM REM R1 = 0.0415 for 3687 Fo > 4sig(Fo) and 0.0451 for all 6113 data REM n/a parameters refined using n/a restraints REM Highest difference peak 0.21, deepest hole -0.23 REM Mean Shift 0, Max Shift 0.000. REM +++ Tabular Listing of Refinement Information +++ REM R1_all = 0.0451 REM R1_gt = 0.0415 REM wR_ref = 0.1164 REM GOOF = 1.032 REM Shift_max = 0.000 REM Shift_mean = 0 REM Reflections_all = 6113 REM Reflections_gt = 3687 REM Parameters = n/a REM Hole = -0.23 REM Peak = 0.21 REM Flack = n/a ; _cod_data_source_file d1nj03642d2.cif _cod_data_source_block 18050301 _cod_database_code 7060971 _shelx_shelxl_version_number 2014/7 _chemical_oxdiff_formula 'C H N O' _chemical_oxdiff_usercomment TPAPLCHO _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. ; _reflns_odcompleteness_completeness 98.47 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 66.97 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups 2.a Aromatic/amide H refined with riding coordinates: C25(H25), C24(H24), C2(H2), C22(H22), C5(H5), C3(H3), C6(H6), C9(H9), C19(H19), C21(H21), C11(H11), C10(H10), C13(H13), C15(H15), C12(H12), C31(H31), C27(H27), C18(H18), C29(H29), C17(H17), C28(H28), C16(H16) ; _olex2_date_sample_data_collection 2018-05-03 _olex2_submission_special_instructions 'No special instructions were received' _oxdiff_exptl_absorpt_empirical_details ; Empirical correction (ABSPACK) includes: - Absorption correction using spherical harmonics - Frame scaling ; _oxdiff_exptl_absorpt_empirical_full_max 1.337 _oxdiff_exptl_absorpt_empirical_full_min 0.707 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, -z' loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_occupancy _atom_site_site_symmetry_order _atom_site_calc_flag _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group O32 O 0.24669(14) 0.23426(13) 0.35800(7) 0.0383(3) Uani 1 1 d . . . . . N26 N -0.04185(15) 0.24831(12) 0.48385(7) 0.0244(2) Uani 1 1 d . . . . . N7 N 1.01936(15) 0.27864(13) 0.84430(8) 0.0277(3) Uani 1 1 d . . . . . C23 C 0.10618(17) 0.25598(15) 0.54014(8) 0.0230(3) Uani 1 1 d . . . . . C4 C 0.55398(17) 0.27225(15) 0.70218(8) 0.0232(3) Uani 1 1 d . . . . . C1 C 0.86433(17) 0.27459(15) 0.79741(8) 0.0240(3) Uani 1 1 d . . . . . C20 C 0.39680(17) 0.26959(14) 0.64844(8) 0.0230(3) Uani 1 1 d . . . . . C25 C 0.41327(18) 0.38672(15) 0.60251(8) 0.0246(3) Uani 1 1 d . . . . . H25 H 0.5221 0.4705 0.6084 0.030 Uiso 1 1 calc R . . . . C30 C -0.03812(19) 0.26117(14) 0.39845(8) 0.0261(3) Uani 1 1 d . . . . . C8 C 1.04552(17) 0.14212(15) 0.86119(8) 0.0242(3) Uani 1 1 d . . . . . C24 C 0.26999(18) 0.37961(15) 0.54838(8) 0.0248(3) Uani 1 1 d . . . . . H24 H 0.2834 0.4575 0.5176 0.030 Uiso 1 1 calc R . . . . C2 C 0.82538(18) 0.41252(15) 0.79908(8) 0.0256(3) Uani 1 1 d . . . . . H2 H 0.9019 0.5065 0.8325 0.031 Uiso 1 1 calc R . . . . C22 C 0.08379(17) 0.14157(14) 0.58759(8) 0.0238(3) Uani 1 1 d . . . . . H22 H -0.0275 0.0611 0.5838 0.029 Uiso 1 1 calc R . . . . C5 C 0.59224(18) 0.13487(15) 0.70162(8) 0.0253(3) Uani 1 1 d . . . . . H5 H 0.5127 0.0404 0.6700 0.030 Uiso 1 1 calc R . . . . C3 C 0.67496(17) 0.41093(15) 0.75177(8) 0.0245(3) Uani 1 1 d . . . . . H3 H 0.6541 0.5044 0.7531 0.029 Uiso 1 1 calc R . . . . C6 C 0.74466(18) 0.13531(15) 0.74659(8) 0.0259(3) Uani 1 1 d . . . . . H6 H 0.7680 0.0424 0.7431 0.031 Uiso 1 1 calc R . . . . C9 C 1.21845(18) 0.12891(16) 0.85604(8) 0.0269(3) Uani 1 1 d . . . . . H9 H 1.3143 0.2087 0.8413 0.032 Uiso 1 1 calc R . . . . C19 C 1.25747(18) 0.51006(16) 0.81507(9) 0.0285(3) Uani 1 1 d . . . . . H19 H 1.2252 0.4734 0.7564 0.034 Uiso 1 1 calc R . . . . C21 C 0.22901(18) 0.14832(14) 0.64071(8) 0.0241(3) Uani 1 1 d . . . . . H21 H 0.2145 0.0707 0.6718 0.029 Uiso 1 1 calc R . . . . C14 C 1.16449(17) 0.42477(15) 0.87320(9) 0.0258(3) Uani 1 1 d . . . . . C11 C 1.10625(19) -0.12311(16) 0.89405(9) 0.0297(3) Uani 1 1 d . . . . . H11 H 1.1260 -0.2117 0.9045 0.036 Uiso 1 1 calc R . . . . C10 C 1.24844(18) -0.00253(17) 0.87275(9) 0.0293(3) Uani 1 1 d . . . . . H10 H 1.3644 -0.0098 0.8696 0.035 Uiso 1 1 calc R . . . . C13 C 0.90397(18) 0.02171(16) 0.88413(9) 0.0281(3) Uani 1 1 d . . . . . H13 H 0.7886 0.0298 0.8891 0.034 Uiso 1 1 calc R . . . . C15 C 1.21290(19) 0.48033(17) 0.96083(9) 0.0312(3) Uani 1 1 d . . . . . H15 H 1.1505 0.4232 0.9998 0.037 Uiso 1 1 calc R . . . . C12 C 0.93479(19) -0.11004(17) 0.89957(9) 0.0307(3) Uani 1 1 d . . . . . H12 H 0.8391 -0.1905 0.9138 0.037 Uiso 1 1 calc R . . . . C31 C 0.1039(2) 0.25378(16) 0.34219(9) 0.0314(3) Uani 1 1 d . . . . . H31 H 0.0842 0.2654 0.2867 0.038 Uiso 1 1 calc R . . . . C27 C -0.21250(19) 0.23450(16) 0.50867(10) 0.0307(3) Uani 1 1 d . . . . . H27 H -0.2504 0.2245 0.5631 0.037 Uiso 1 1 calc R . . . . C18 C 1.39914(19) 0.65065(17) 0.84497(10) 0.0323(3) Uani 1 1 d . . . . . H18 H 1.4620 0.7077 0.8061 0.039 Uiso 1 1 calc R . . . . C29 C -0.2109(2) 0.25489(15) 0.37199(10) 0.0318(3) Uani 1 1 d . . . . . H29 H -0.2475 0.2612 0.3176 0.038 Uiso 1 1 calc R . . . . C17 C 1.44725(18) 0.70628(17) 0.93252(11) 0.0339(3) Uani 1 1 d . . . . . H17 H 1.5417 0.8005 0.9522 0.041 Uiso 1 1 calc R . . . . C28 C -0.32014(19) 0.23757(16) 0.44086(10) 0.0331(3) Uani 1 1 d . . . . . H28 H -0.4422 0.2296 0.4409 0.040 Uiso 1 1 calc R . . . . C16 C 1.3543(2) 0.62105(18) 0.99035(10) 0.0356(3) Uani 1 1 d . . . . . H16 H 1.3865 0.6579 1.0490 0.043 Uiso 1 1 calc R . . . . 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 O32 0.0342(6) 0.0434(6) 0.0333(5) 0.0028(5) 0.0053(4) 0.0109(5) N26 0.0254(5) 0.0230(5) 0.0255(5) 0.0051(4) 0.0014(4) 0.0093(4) N7 0.0251(5) 0.0244(5) 0.0325(6) 0.0065(5) -0.0036(5) 0.0066(4) C23 0.0264(6) 0.0235(6) 0.0205(6) 0.0030(5) 0.0025(5) 0.0112(5) C4 0.0220(6) 0.0249(6) 0.0226(6) 0.0061(5) 0.0044(5) 0.0072(5) C1 0.0223(6) 0.0266(6) 0.0239(6) 0.0069(5) 0.0031(5) 0.0083(5) C20 0.0256(6) 0.0222(6) 0.0208(6) 0.0027(5) 0.0031(5) 0.0087(5) C25 0.0251(6) 0.0208(6) 0.0248(6) 0.0040(5) 0.0029(5) 0.0042(5) C30 0.0320(7) 0.0195(6) 0.0257(6) 0.0063(5) -0.0025(5) 0.0067(5) C8 0.0252(6) 0.0263(6) 0.0213(6) 0.0053(5) -0.0004(5) 0.0090(5) C24 0.0312(7) 0.0209(6) 0.0229(6) 0.0062(5) 0.0038(5) 0.0089(5) C2 0.0246(6) 0.0223(6) 0.0261(6) 0.0010(5) -0.0002(5) 0.0057(5) C22 0.0238(6) 0.0219(6) 0.0235(6) 0.0044(5) 0.0030(5) 0.0053(5) C5 0.0260(6) 0.0219(6) 0.0248(6) 0.0035(5) 0.0004(5) 0.0048(5) C3 0.0254(6) 0.0217(6) 0.0271(6) 0.0049(5) 0.0034(5) 0.0092(5) C6 0.0290(6) 0.0226(6) 0.0271(6) 0.0059(5) 0.0021(5) 0.0096(5) C9 0.0241(6) 0.0291(7) 0.0254(6) 0.0057(5) 0.0017(5) 0.0067(5) C19 0.0287(6) 0.0299(7) 0.0300(7) 0.0064(5) 0.0053(5) 0.0138(5) C21 0.0280(6) 0.0218(6) 0.0232(6) 0.0070(5) 0.0031(5) 0.0081(5) C14 0.0223(6) 0.0243(6) 0.0318(7) 0.0052(5) -0.0001(5) 0.0096(5) C11 0.0335(7) 0.0283(7) 0.0300(7) 0.0065(5) 0.0006(5) 0.0138(6) C10 0.0264(6) 0.0332(7) 0.0299(7) 0.0036(5) 0.0015(5) 0.0141(5) C13 0.0248(6) 0.0334(7) 0.0286(6) 0.0093(5) 0.0033(5) 0.0117(5) C15 0.0283(7) 0.0344(7) 0.0303(7) 0.0086(6) 0.0002(5) 0.0091(6) C12 0.0290(7) 0.0311(7) 0.0322(7) 0.0112(6) 0.0039(5) 0.0081(5) C31 0.0365(7) 0.0273(7) 0.0247(6) 0.0067(5) 0.0007(5) 0.0027(6) C27 0.0289(7) 0.0308(7) 0.0334(7) 0.0044(6) 0.0049(5) 0.0129(5) C18 0.0250(6) 0.0310(7) 0.0448(8) 0.0123(6) 0.0100(6) 0.0119(5) C29 0.0372(7) 0.0227(6) 0.0348(7) 0.0053(5) -0.0093(6) 0.0098(5) C17 0.0212(6) 0.0280(7) 0.0488(9) 0.0026(6) -0.0010(6) 0.0067(5) C28 0.0278(7) 0.0262(7) 0.0443(8) 0.0004(6) -0.0044(6) 0.0122(5) C16 0.0299(7) 0.0372(8) 0.0354(8) 0.0011(6) -0.0045(6) 0.0097(6) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 '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 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 '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 C30 N26 C23 127.76(11) . . ? C27 N26 C23 123.95(11) . . ? C27 N26 C30 108.22(11) . . ? C1 N7 C8 123.10(11) . . ? C1 N7 C14 119.52(11) . . ? C8 N7 C14 117.29(11) . . ? C24 C23 N26 119.86(11) . . ? C22 C23 N26 119.78(11) . . ? C22 C23 C24 120.34(12) . . ? C5 C4 C20 120.71(11) . . ? C3 C4 C20 122.12(11) . . ? C3 C4 C5 117.09(12) . . ? N7 C1 C2 120.45(12) . . ? C6 C1 N7 121.99(11) . . ? C6 C1 C2 117.55(12) . . ? C25 C20 C4 120.85(11) . . ? C21 C20 C4 121.04(11) . . ? C21 C20 C25 118.10(12) . . ? C20 C25 H25 119.5 . . ? C24 C25 C20 120.94(12) . . ? C24 C25 H25 119.5 . . ? N26 C30 C31 127.29(12) . . ? N26 C30 C29 107.06(12) . . ? C29 C30 C31 124.78(13) . . ? C9 C8 N7 119.18(12) . . ? C13 C8 N7 121.99(12) . . ? C13 C8 C9 118.83(12) . . ? C23 C24 H24 120.1 . . ? C25 C24 C23 119.87(11) . . ? C25 C24 H24 120.1 . . ? C1 C2 H2 119.4 . . ? C3 C2 C1 121.13(12) . . ? C3 C2 H2 119.4 . . ? C23 C22 H22 120.3 . . ? C21 C22 C23 119.38(12) . . ? C21 C22 H22 120.3 . . ? C4 C5 H5 119.0 . . ? C6 C5 C4 122.03(12) . . ? C6 C5 H5 119.0 . . ? C4 C3 H3 119.2 . . ? C2 C3 C4 121.51(12) . . ? C2 C3 H3 119.2 . . ? C1 C6 H6 119.7 . . ? C5 C6 C1 120.65(12) . . ? C5 C6 H6 119.7 . . ? C8 C9 H9 119.8 . . ? C10 C9 C8 120.49(12) . . ? C10 C9 H9 119.8 . . ? C14 C19 H19 120.2 . . ? C14 C19 C18 119.68(14) . . ? C18 C19 H19 120.2 . . ? C20 C21 H21 119.4 . . ? C22 C21 C20 121.30(11) . . ? C22 C21 H21 119.4 . . ? C19 C14 N7 120.97(13) . . ? C19 C14 C15 119.92(13) . . ? C15 C14 N7 119.11(12) . . ? C10 C11 H11 120.4 . . ? C12 C11 H11 120.4 . . ? C12 C11 C10 119.27(13) . . ? C9 C10 H10 119.8 . . ? C11 C10 C9 120.37(12) . . ? C11 C10 H10 119.8 . . ? C8 C13 H13 119.9 . . ? C12 C13 C8 120.23(12) . . ? C12 C13 H13 119.9 . . ? C14 C15 H15 119.9 . . ? C16 C15 C14 120.15(14) . . ? C16 C15 H15 119.9 . . ? C11 C12 C13 120.80(13) . . ? C11 C12 H12 119.6 . . ? C13 C12 H12 119.6 . . ? O32 C31 C30 128.29(13) . . ? O32 C31 H31 115.9 . . ? C30 C31 H31 115.9 . . ? N26 C27 H27 125.2 . . ? N26 C27 C28 109.59(13) . . ? C28 C27 H27 125.2 . . ? C19 C18 H18 119.8 . . ? C17 C18 C19 120.39(13) . . ? C17 C18 H18 119.8 . . ? C30 C29 H29 125.8 . . ? C30 C29 C28 108.42(13) . . ? C28 C29 H29 125.8 . . ? C18 C17 H17 120.1 . . ? C16 C17 C18 119.82(13) . . ? C16 C17 H17 120.1 . . ? C27 C28 C29 106.72(12) . . ? C27 C28 H28 126.6 . . ? C29 C28 H28 126.6 . . ? C15 C16 H16 120.0 . . ? C17 C16 C15 120.04(14) . . ? C17 C16 H16 120.0 . . ? 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 O32 C31 1.2190(19) . ? N26 C23 1.4319(16) . ? N26 C30 1.3885(17) . ? N26 C27 1.3625(18) . ? N7 C1 1.4036(16) . ? N7 C8 1.4227(17) . ? N7 C14 1.4337(17) . ? C23 C24 1.3888(19) . ? C23 C22 1.3878(18) . ? C4 C20 1.4820(17) . ? C4 C5 1.4001(18) . ? C4 C3 1.3957(19) . ? C1 C2 1.4049(18) . ? C1 C6 1.4028(19) . ? C20 C25 1.3991(18) . ? C20 C21 1.3991(18) . ? C25 H25 0.9300 . ? C25 C24 1.3837(18) . ? C30 C31 1.439(2) . ? C30 C29 1.3889(19) . ? C8 C9 1.3955(18) . ? C8 C13 1.3955(19) . ? C24 H24 0.9300 . ? C2 H2 0.9300 . ? C2 C3 1.3852(18) . ? C22 H22 0.9300 . ? C22 C21 1.3871(18) . ? C5 H5 0.9300 . ? C5 C6 1.3830(18) . ? C3 H3 0.9300 . ? C6 H6 0.9300 . ? C9 H9 0.9300 . ? C9 C10 1.3891(19) . ? C19 H19 0.9300 . ? C19 C14 1.388(2) . ? C19 C18 1.392(2) . ? C21 H21 0.9300 . ? C14 C15 1.391(2) . ? C11 H11 0.9300 . ? C11 C10 1.388(2) . ? C11 C12 1.384(2) . ? C10 H10 0.9300 . ? C13 H13 0.9300 . ? C13 C12 1.3876(19) . ? C15 H15 0.9300 . ? C15 C16 1.390(2) . ? C12 H12 0.9300 . ? C31 H31 0.9300 . ? C27 H27 0.9300 . ? C27 C28 1.375(2) . ? C18 H18 0.9300 . ? C18 C17 1.389(2) . ? C29 H29 0.9300 . ? C29 C28 1.394(2) . ? C17 H17 0.9300 . ? C17 C16 1.384(2) . ? C28 H28 0.9300 . ? C16 H16 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 N26 C23 C24 C25 -179.75(11) . . . . ? N26 C23 C22 C21 178.79(11) . . . . ? N26 C30 C31 O32 0.4(2) . . . . ? N26 C30 C29 C28 -0.25(15) . . . . ? N26 C27 C28 C29 -0.36(16) . . . . ? N7 C1 C2 C3 178.68(12) . . . . ? N7 C1 C6 C5 179.52(12) . . . . ? N7 C8 C9 C10 179.57(12) . . . . ? N7 C8 C13 C12 179.60(12) . . . . ? N7 C14 C15 C16 179.41(12) . . . . ? C23 N26 C30 C31 13.5(2) . . . . ? C23 N26 C30 C29 -176.86(11) . . . . ? C23 N26 C27 C28 177.24(11) . . . . ? C23 C22 C21 C20 1.02(19) . . . . ? C4 C20 C25 C24 176.19(11) . . . . ? C4 C20 C21 C22 -177.17(11) . . . . ? C4 C5 C6 C1 2.3(2) . . . . ? C1 N7 C8 C9 139.53(13) . . . . ? C1 N7 C8 C13 -41.51(19) . . . . ? C1 N7 C14 C19 -60.59(17) . . . . ? C1 N7 C14 C15 119.95(14) . . . . ? C1 C2 C3 C4 1.5(2) . . . . ? C20 C4 C5 C6 175.62(12) . . . . ? C20 C4 C3 C2 -177.43(11) . . . . ? C20 C25 C24 C23 0.94(19) . . . . ? C25 C20 C21 C22 1.49(19) . . . . ? C30 N26 C23 C24 50.60(18) . . . . ? C30 N26 C23 C22 -130.80(13) . . . . ? C30 N26 C27 C28 0.21(15) . . . . ? C30 C29 C28 C27 0.38(16) . . . . ? C8 N7 C1 C2 165.45(12) . . . . ? C8 N7 C1 C6 -15.48(19) . . . . ? C8 N7 C14 C19 116.09(14) . . . . ? C8 N7 C14 C15 -63.37(17) . . . . ? C8 C9 C10 C11 0.6(2) . . . . ? C8 C13 C12 C11 1.2(2) . . . . ? C24 C23 C22 C21 -2.62(18) . . . . ? C2 C1 C6 C5 -1.39(19) . . . . ? C22 C23 C24 C25 1.66(19) . . . . ? C5 C4 C20 C25 -137.28(13) . . . . ? C5 C4 C20 C21 41.34(17) . . . . ? C5 C4 C3 C2 -0.63(19) . . . . ? C3 C4 C20 C25 39.40(18) . . . . ? C3 C4 C20 C21 -141.97(13) . . . . ? C3 C4 C5 C6 -1.22(19) . . . . ? C6 C1 C2 C3 -0.43(19) . . . . ? C9 C8 C13 C12 -1.4(2) . . . . ? C19 C14 C15 C16 -0.1(2) . . . . ? C19 C18 C17 C16 0.3(2) . . . . ? C21 C20 C25 C24 -2.48(19) . . . . ? C14 N7 C1 C2 -18.07(18) . . . . ? C14 N7 C1 C6 160.99(12) . . . . ? C14 N7 C8 C9 -37.02(18) . . . . ? C14 N7 C8 C13 141.94(13) . . . . ? C14 C19 C18 C17 -0.3(2) . . . . ? C14 C15 C16 C17 0.0(2) . . . . ? C10 C11 C12 C13 0.0(2) . . . . ? C13 C8 C9 C10 0.6(2) . . . . ? C12 C11 C10 C9 -0.8(2) . . . . ? C31 C30 C29 C28 169.71(13) . . . . ? C27 N26 C23 C24 -125.83(14) . . . . ? C27 N26 C23 C22 52.77(17) . . . . ? C27 N26 C30 C31 -169.60(13) . . . . ? C27 N26 C30 C29 0.03(14) . . . . ? C18 C19 C14 N7 -179.27(12) . . . . ? C18 C19 C14 C15 0.2(2) . . . . ? C18 C17 C16 C15 -0.2(2) . . . . ? C29 C30 C31 O32 -167.51(14) . . . . ?