#------------------------------------------------------------------------------ #$Date: 2020-04-22 01:36:37 +0300 (Wed, 22 Apr 2020) $ #$Revision: 250996 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/03/7240367.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_7240367 loop_ _publ_author_name 'He, Xinrui' 'Zhao, Jian' 'Tan, Zeqing' 'Zhao, Jiaxin' 'Cheng, Xiao' 'Zhou, Chuanjian' _publ_section_title ; Chalcone single crystals with red emission and photodimerization-triggered hopping behavior: the substituent effect and molecular packing effect ; _journal_name_full CrystEngComm _journal_paper_doi 10.1039/D0CE00404A _journal_year 2020 _chemical_formula_moiety 'C18 H16 I N O' _chemical_formula_sum 'C18 H16 I N O' _chemical_formula_weight 389.22 _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 _atom_sites_solution_primary dual _audit_creation_date 2020-01-13 _audit_creation_method ; Olex2 1.2 (compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) ; _audit_update_record ; 2020-01-13 deposited with the CCDC. 2020-04-21 downloaded from the CCDC. ; _cell_angle_alpha 96.102(5) _cell_angle_beta 104.127(4) _cell_angle_gamma 93.993(5) _cell_formula_units_Z 2 _cell_length_a 6.8569(3) _cell_length_b 9.5546(6) _cell_length_c 12.4049(6) _cell_measurement_reflns_used 4731 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 75.6860 _cell_measurement_theta_min 5.5400 _cell_volume 779.80(7) _computing_cell_refinement 'CrysAlisPro 1.171.40.25a (Rigaku OD, 2018)' _computing_data_collection 'CrysAlisPro 1.171.40.25a (Rigaku OD, 2018)' _computing_data_reduction 'CrysAlisPro 1.171.40.25a (Rigaku OD, 2018)' _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2015)' _computing_structure_solution 'ShelXT (Sheldrick, 2015)' _diffrn_ambient_temperature 293(2) _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 10.0000 _diffrn_detector_type HyPix _diffrn_measured_fraction_theta_full 0.972 _diffrn_measured_fraction_theta_max 0.981 _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 -117.00 -91.00 1.00 0.10 -- -48.45 -35.00 112.00 26 2 \w -79.00 -36.00 1.00 0.10 -- -48.45 -35.00 112.00 43 3 \w -25.00 5.00 1.00 0.10 -- 48.45 -35.00 112.00 30 4 \w 44.00 122.00 1.00 0.10 -- 48.45 35.00 -91.00 78 5 \w -99.00 -73.00 1.00 0.90 -- -86.25 -35.00 112.00 26 6 \w -160.00-105.00 1.00 0.90 -- -86.25 -35.00 112.00 55 7 \w 94.00 151.00 1.00 0.90 -- 106.49 35.00 -91.00 57 8 \w 69.00 118.00 1.00 0.90 -- 106.49 -35.00 112.00 49 9 \w -41.00 12.00 1.00 0.10 -- -48.45 35.00 -91.00 53 10 \w 35.00 95.00 1.00 0.10 -- 48.45-125.00 -30.00 60 11 \w -97.00 -13.00 1.00 0.90 -- -86.25 77.00 60.00 84 12 \w -98.00 -21.00 1.00 0.90 -- -86.25 35.00 -91.00 77 13 \w 35.00 122.00 1.00 0.90 -- 106.49 -77.00-180.00 87 14 \w 76.00 115.00 1.00 0.90 -- 106.49 -19.00 -90.00 39 15 \w 32.00 71.00 1.00 0.90 -- 106.49 -19.00 -90.00 39 16 \w 36.00 117.00 1.00 0.90 -- 106.49-125.00 150.00 81 17 \w 37.00 109.00 1.00 0.90 -- 106.49 -99.00 150.00 72 18 \w 136.00 177.00 1.00 0.90 -- 106.49 19.00 -30.00 41 19 \w 101.00 133.00 1.00 0.90 -- 106.49 19.00 -30.00 32 20 \w 36.00 81.00 1.00 0.90 -- 106.49 -38.00 -60.00 45 21 \w 86.00 112.00 1.00 0.90 -- 106.49 -38.00 -60.00 26 22 \w 41.00 102.00 1.00 0.90 -- 106.49 -99.00 -60.00 61 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'XtaLAB Synergy, Dualflex, HyPix' _diffrn_measurement_method '\w scans' _diffrn_measurement_specimen_support 'Mitegen 50um' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 -0.1745645000 _diffrn_orient_matrix_UB_12 0.0182316000 _diffrn_orient_matrix_UB_13 0.0567644000 _diffrn_orient_matrix_UB_21 -0.0165510000 _diffrn_orient_matrix_UB_22 -0.1594789000 _diffrn_orient_matrix_UB_23 0.0100312000 _diffrn_orient_matrix_UB_31 0.1531711000 _diffrn_orient_matrix_UB_32 0.0281004000 _diffrn_orient_matrix_UB_33 0.1155333000 _diffrn_radiation_collimation 0.3 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0296 _diffrn_reflns_av_unetI/netI 0.0329 _diffrn_reflns_Laue_measured_fraction_full 0.972 _diffrn_reflns_Laue_measured_fraction_max 0.981 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 14 _diffrn_reflns_limit_l_min -11 _diffrn_reflns_number 6316 _diffrn_reflns_point_group_measured_fraction_full 0.972 _diffrn_reflns_point_group_measured_fraction_max 0.981 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 67.076 _diffrn_reflns_theta_min 5.588 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_current 24.0 _diffrn_source_power 1.2 _diffrn_source_target Mo _diffrn_source_type 'PhotonJet (Cu) X-ray Source' _diffrn_source_voltage 50.0 _exptl_absorpt_coefficient_mu 16.108 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.42512 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.40.25a (Rigaku Oxford Diffraction, 2018) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour 'clear light orange' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier light _exptl_crystal_colour_primary orange _exptl_crystal_density_diffrn 1.658 _exptl_crystal_description block _exptl_crystal_F_000 384 _exptl_crystal_size_max 0.08 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.04 _refine_diff_density_max 0.465 _refine_diff_density_min -0.743 _refine_diff_density_rms 0.069 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.076 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 192 _refine_ls_number_reflns 2749 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.076 _refine_ls_R_factor_all 0.0374 _refine_ls_R_factor_gt 0.0306 _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^)+(0.0370P)^2^+0.4458P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0744 _refine_ls_wR_factor_ref 0.0811 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2470 _reflns_number_total 2749 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0ce00404a5.cif _cod_data_source_block 190717zcj4 _cod_database_code 7240367 _shelxl_version_number 2013-4 _chemical_oxdiff_formula ICNO _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 98.54 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 66.97 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups At 1.5 times of: All C(H,H,H) groups 2.a Secondary CH2 refined with riding coordinates: C5(H5A,H5B) 2.b Aromatic/amide H refined with riding coordinates: C2(H2), C8(H8), C10(H10), C11(H11), C12(H12), C14(H14), C15(H15), C16(H16) 2.c Idealised Me refined as rotating group: C17(H17A,H17B,H17C), C18(H18A,H18B,H18C) ; _shelx_res_file ; TITL 190717zcj4_a.res in P-1 REM Old TITL 190717ZCJ4 in P-1 REM SHELXT solution in P-1 REM R1 0.206, Rweak 0.028, Alpha 0.053, Orientation as input REM Formula found by SHELXT: C17 O I CELL 1.54184 6.8569 9.5546 12.4049 96.102 104.127 93.993 ZERR 2 0.0003 0.0006 0.0006 0.005 0.004 0.005 LATT 1 SFAC C H I N O UNIT 36 32 2 2 2 L.S. 10 PLAN 2 TEMP 20(2) LIST 6 fmap 2 acta SHEL 999 0.837 OMIT 3 -1 12 OMIT 3 -8 8 OMIT -1 -3 14 OMIT -4 -3 14 OMIT 3 -2 12 OMIT 4 1 9 OMIT -1 -10 7 OMIT 4 -4 10 OMIT 6 -2 7 OMIT 2 -2 13 OMIT 4 2 9 REM REM REM WGHT 0.037000 0.445800 FVAR 5.18811 I1 3 0.032328 0.840059 -0.164850 11.00000 0.06206 0.09965 = 0.06598 0.04034 0.00985 0.00710 O1 5 0.924840 0.630785 0.193139 11.00000 0.03992 0.11329 = 0.08454 0.02730 0.01626 0.00070 N1 4 0.462790 0.138732 0.628119 11.00000 0.07242 0.07378 = 0.06604 0.02969 0.01785 0.01785 C1 1 0.622489 0.529536 0.235770 11.00000 0.03877 0.05545 = 0.04661 0.00292 0.01005 0.00413 C2 1 0.234384 0.679122 0.023085 11.00000 0.04213 0.05782 = 0.04823 0.00825 0.01129 -0.00117 AFIX 43 H2 2 0.102534 0.649771 0.023749 11.00000 -1.20000 AFIX 0 C3 1 0.398655 0.634105 0.096003 11.00000 0.04320 0.04829 = 0.03788 0.00075 0.01229 -0.00117 C4 1 0.593783 0.678912 0.092679 11.00000 0.04459 0.05318 = 0.04283 0.00054 0.01402 -0.00020 C5 1 0.399382 0.538544 0.185180 11.00000 0.04026 0.05250 = 0.04652 0.00752 0.00953 0.00095 AFIX 23 H5A 2 0.330547 0.445920 0.152826 11.00000 -1.20000 H5B 2 0.334891 0.578863 0.241052 11.00000 -1.20000 AFIX 0 C6 1 0.643374 0.379358 0.395763 11.00000 0.04207 0.04936 = 0.04939 0.00458 0.00519 0.00852 C7 1 0.739535 0.615205 0.176508 11.00000 0.04147 0.06621 = 0.05129 0.00426 0.01432 0.00105 C8 1 0.717072 0.463443 0.320874 11.00000 0.03797 0.06175 = 0.05402 0.00474 0.00829 0.00636 AFIX 43 H8 2 0.857139 0.473602 0.334393 11.00000 -1.20000 AFIX 0 C9 1 0.521387 0.216118 0.552032 11.00000 0.05880 0.04828 = 0.04888 0.00411 0.01020 0.01480 C10 1 0.380506 0.267418 0.467147 11.00000 0.04377 0.05989 = 0.04884 0.00952 0.00508 0.00551 AFIX 43 H10 2 0.243393 0.247155 0.461268 11.00000 -1.20000 AFIX 0 C11 1 0.630585 0.771317 0.019591 11.00000 0.04688 0.06978 = 0.05912 0.00831 0.02110 -0.00863 AFIX 43 H11 2 0.762426 0.802141 0.019914 11.00000 -1.20000 AFIX 0 C12 1 0.439035 0.346827 0.392297 11.00000 0.04173 0.05789 = 0.05100 0.00975 0.00114 0.00829 AFIX 43 H12 2 0.340515 0.379916 0.337851 11.00000 -1.20000 AFIX 0 C13 1 0.274592 0.769644 -0.050851 11.00000 0.05224 0.06036 = 0.04243 0.00998 0.00979 0.00154 C14 1 0.469767 0.816987 -0.053520 11.00000 0.06035 0.06845 = 0.05724 0.01565 0.02208 -0.00261 AFIX 43 H14 2 0.491052 0.878375 -0.103814 11.00000 -1.20000 AFIX 0 C15 1 0.725736 0.250710 0.557604 11.00000 0.05170 0.07241 = 0.05720 0.01990 0.00214 0.02035 AFIX 43 H15 2 0.824571 0.220620 0.613648 11.00000 -1.20000 AFIX 0 C16 1 0.781770 0.328383 0.481439 11.00000 0.04141 0.07279 = 0.06366 0.01296 0.00520 0.01553 AFIX 43 H16 2 0.918897 0.348141 0.487099 11.00000 -1.20000 AFIX 0 C17 1 0.254284 0.094649 0.617485 11.00000 0.08490 0.07752 = 0.07443 0.01529 0.02658 -0.00362 AFIX 137 H17A 2 0.178470 0.175532 0.612799 11.00000 -1.50000 H17B 2 0.241546 0.050304 0.681670 11.00000 -1.50000 H17C 2 0.203072 0.028562 0.550860 11.00000 -1.50000 AFIX 0 C18 1 0.608772 0.073262 0.707441 11.00000 0.11165 0.07711 = 0.06231 0.02832 0.01946 0.03516 AFIX 137 H18A 2 0.646517 -0.009568 0.669683 11.00000 -1.50000 H18B 2 0.550110 0.047007 0.766088 11.00000 -1.50000 H18C 2 0.726427 0.138964 0.739116 11.00000 -1.50000 AFIX 0 HKLF 4 REM 190717zcj4_a.res in P-1 REM R1 = 0.0306 for 2470 Fo > 4sig(Fo) and 0.0374 for all 2749 data REM 192 parameters refined using 0 restraints END WGHT 0.0368 0.4454 REM Highest difference peak 0.465, deepest hole -0.743, 1-sigma level 0.069 Q1 1 0.1193 0.8469 -0.0982 11.00000 0.05 0.46 Q2 1 0.0141 0.9199 -0.1176 11.00000 0.05 0.43 ; _shelx_res_checksum 84734 _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 1.662 _oxdiff_exptl_absorpt_empirical_full_min 0.562 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 I1 I 0.03233(4) 0.84006(3) -0.16485(2) 0.07484(13) Uani 1 1 d . . . . . O1 O 0.9248(4) 0.6308(4) 0.1931(3) 0.0784(8) Uani 1 1 d . . . . . N1 N 0.4628(5) 0.1387(4) 0.6281(3) 0.0686(8) Uani 1 1 d . . . . . C1 C 0.6225(4) 0.5295(3) 0.2358(3) 0.0474(7) Uani 1 1 d . . . . . C2 C 0.2344(5) 0.6791(4) 0.0231(3) 0.0496(7) Uani 1 1 d . . . . . H2 H 0.1025 0.6498 0.0237 0.060 Uiso 1 1 calc R . . . . C3 C 0.3987(4) 0.6341(3) 0.0960(2) 0.0434(6) Uani 1 1 d . . . . . C4 C 0.5938(5) 0.6789(3) 0.0927(3) 0.0470(7) Uani 1 1 d . . . . . C5 C 0.3994(4) 0.5385(3) 0.1852(3) 0.0468(7) Uani 1 1 d . . . . . H5A H 0.3305 0.4459 0.1528 0.056 Uiso 1 1 calc R . . . . H5B H 0.3349 0.5789 0.2411 0.056 Uiso 1 1 calc R . . . . C6 C 0.6434(4) 0.3794(3) 0.3958(3) 0.0480(7) Uani 1 1 d . . . . . C7 C 0.7395(5) 0.6152(4) 0.1765(3) 0.0530(7) Uani 1 1 d . . . . . C8 C 0.7171(5) 0.4634(4) 0.3209(3) 0.0520(7) Uani 1 1 d . . . . . H8 H 0.8571 0.4736 0.3344 0.062 Uiso 1 1 calc R . . . . C9 C 0.5214(5) 0.2161(3) 0.5520(3) 0.0523(7) Uani 1 1 d . . . . . C10 C 0.3805(5) 0.2674(4) 0.4671(3) 0.0518(7) Uani 1 1 d . . . . . H10 H 0.2434 0.2472 0.4613 0.062 Uiso 1 1 calc R . . . . C11 C 0.6306(5) 0.7713(4) 0.0196(3) 0.0579(8) Uani 1 1 d . . . . . H11 H 0.7624 0.8021 0.0199 0.070 Uiso 1 1 calc R . . . . C12 C 0.4390(5) 0.3468(4) 0.3923(3) 0.0517(7) Uani 1 1 d . . . . . H12 H 0.3405 0.3799 0.3379 0.062 Uiso 1 1 calc R . . . . C13 C 0.2746(5) 0.7696(4) -0.0509(3) 0.0520(7) Uani 1 1 d . . . . . C14 C 0.4698(6) 0.8170(4) -0.0535(3) 0.0606(8) Uani 1 1 d . . . . . H14 H 0.4911 0.8784 -0.1038 0.073 Uiso 1 1 calc R . . . . C15 C 0.7257(5) 0.2507(4) 0.5576(3) 0.0609(9) Uani 1 1 d . . . . . H15 H 0.8246 0.2206 0.6136 0.073 Uiso 1 1 calc R . . . . C16 C 0.7818(5) 0.3284(4) 0.4814(3) 0.0599(8) Uani 1 1 d . . . . . H16 H 0.9189 0.3481 0.4871 0.072 Uiso 1 1 calc R . . . . C17 C 0.2543(7) 0.0946(5) 0.6175(4) 0.0780(11) Uani 1 1 d . . . . . H17A H 0.1785 0.1755 0.6128 0.117 Uiso 1 1 calc GR . . . . H17B H 0.2415 0.0503 0.6817 0.117 Uiso 1 1 calc GR . . . . H17C H 0.2031 0.0286 0.5509 0.117 Uiso 1 1 calc GR . . . . C18 C 0.6088(8) 0.0733(5) 0.7074(4) 0.0814(12) Uani 1 1 d . . . . . H18A H 0.6465 -0.0096 0.6697 0.122 Uiso 1 1 calc GR . . . . H18B H 0.5501 0.0470 0.7661 0.122 Uiso 1 1 calc GR . . . . H18C H 0.7264 0.1390 0.7391 0.122 Uiso 1 1 calc GR . . . . 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 I1 0.06206(17) 0.0996(2) 0.06598(19) 0.04034(14) 0.00985(12) 0.00710(13) O1 0.0399(13) 0.113(2) 0.0845(19) 0.0273(17) 0.0163(12) 0.0007(13) N1 0.072(2) 0.074(2) 0.0660(19) 0.0297(16) 0.0179(15) 0.0178(16) C1 0.0388(14) 0.0555(17) 0.0466(17) 0.0029(14) 0.0101(13) 0.0041(12) C2 0.0421(15) 0.0578(18) 0.0482(17) 0.0082(14) 0.0113(13) -0.0012(13) C3 0.0432(15) 0.0483(16) 0.0379(15) 0.0008(12) 0.0123(12) -0.0012(12) C4 0.0446(15) 0.0532(17) 0.0428(16) 0.0005(13) 0.0140(13) -0.0002(12) C5 0.0403(15) 0.0525(16) 0.0465(17) 0.0075(13) 0.0095(13) 0.0009(12) C6 0.0421(15) 0.0494(16) 0.0494(18) 0.0046(13) 0.0052(13) 0.0085(12) C7 0.0415(16) 0.066(2) 0.0513(19) 0.0043(15) 0.0143(14) 0.0010(14) C8 0.0380(15) 0.0617(19) 0.0540(19) 0.0047(15) 0.0083(13) 0.0064(13) C9 0.0588(19) 0.0483(17) 0.0489(18) 0.0041(14) 0.0102(14) 0.0148(14) C10 0.0438(16) 0.0599(18) 0.0488(18) 0.0095(15) 0.0051(13) 0.0055(13) C11 0.0469(17) 0.070(2) 0.059(2) 0.0083(17) 0.0211(15) -0.0086(15) C12 0.0417(16) 0.0579(18) 0.0510(18) 0.0097(15) 0.0011(13) 0.0083(13) C13 0.0522(17) 0.0604(19) 0.0424(17) 0.0100(14) 0.0098(13) 0.0015(14) C14 0.060(2) 0.068(2) 0.057(2) 0.0157(17) 0.0221(16) -0.0026(16) C15 0.0517(18) 0.072(2) 0.057(2) 0.0199(17) 0.0021(15) 0.0204(16) C16 0.0414(16) 0.073(2) 0.064(2) 0.0130(17) 0.0052(15) 0.0155(15) C17 0.085(3) 0.078(3) 0.074(3) 0.015(2) 0.027(2) -0.004(2) C18 0.112(4) 0.077(3) 0.062(2) 0.028(2) 0.019(2) 0.035(2) 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' I I -0.3257 6.8362 '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 C9 N1 C17 121.3(3) . . ? C9 N1 C18 121.1(4) . . ? C17 N1 C18 116.3(4) . . ? C7 C1 C5 108.3(3) . . ? C8 C1 C5 131.1(3) . . ? C8 C1 C7 120.5(3) . . ? C13 C2 C3 117.4(3) . . ? C2 C3 C4 120.1(3) . . ? C2 C3 C5 128.6(3) . . ? C4 C3 C5 111.3(3) . . ? C3 C4 C7 109.5(3) . . ? C11 C4 C3 121.6(3) . . ? C11 C4 C7 128.9(3) . . ? C3 C5 C1 103.5(2) . . ? C12 C6 C8 125.1(3) . . ? C16 C6 C8 119.3(3) . . ? C16 C6 C12 115.5(3) . . ? O1 C7 C1 126.8(3) . . ? O1 C7 C4 125.9(3) . . ? C4 C7 C1 107.3(3) . . ? C1 C8 C6 132.4(3) . . ? N1 C9 C10 121.9(3) . . ? N1 C9 C15 121.4(3) . . ? C15 C9 C10 116.7(3) . . ? C12 C10 C9 121.9(3) . . ? C14 C11 C4 119.2(3) . . ? C10 C12 C6 121.8(3) . . ? C2 C13 I1 119.3(2) . . ? C2 C13 C14 123.0(3) . . ? C14 C13 I1 117.8(3) . . ? C11 C14 C13 118.8(3) . . ? C16 C15 C9 120.8(3) . . ? C15 C16 C6 123.3(3) . . ? 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 I1 C13 2.103(3) . ? O1 C7 1.232(4) . ? N1 C9 1.375(5) . ? N1 C17 1.432(6) . ? N1 C18 1.449(5) . ? C1 C5 1.517(4) . ? C1 C7 1.476(5) . ? C1 C8 1.341(5) . ? C2 C3 1.387(5) . ? C2 C13 1.387(5) . ? C3 C4 1.388(4) . ? C3 C5 1.507(4) . ? C4 C7 1.471(5) . ? C4 C11 1.384(5) . ? C6 C8 1.447(5) . ? C6 C12 1.403(4) . ? C6 C16 1.396(5) . ? C9 C10 1.400(5) . ? C9 C15 1.400(5) . ? C10 C12 1.374(5) . ? C11 C14 1.375(6) . ? C13 C14 1.392(5) . ? C15 C16 1.370(6) . ?