#------------------------------------------------------------------------------ #$Date: 2020-10-06 14:05:59 +0300 (Tue, 06 Oct 2020) $ #$Revision: 257937 $ #$URL: file:///home/coder/svn-repositories/cod/cif/1/55/77/1557775.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_1557775 loop_ _publ_author_name 'Li, Baixue' 'Qin, Anjun' 'Tang, Ben Zhong' _publ_section_title ; Metal-free polycycloaddition of aldehyde-activated internal diynes and diazides toward post-functionalizable poly(formyl-1,2,3-triazole)s ; _journal_issue 17 _journal_name_full 'Polymer Chemistry' _journal_page_first 3075 _journal_page_last 3083 _journal_paper_doi 10.1039/D0PY00193G _journal_volume 11 _journal_year 2020 _chemical_formula_moiety 'C16 H13 N3 O' _chemical_formula_sum 'C16 H13 N3 O' _chemical_formula_weight 263.29 _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 2019-05-16 _audit_creation_method ; Olex2 1.2 (compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) ; _audit_update_record ; 2019-10-12 deposited with the CCDC. 2020-04-09 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 109.249(6) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 13.1254(7) _cell_length_b 8.1029(4) _cell_length_c 12.6860(7) _cell_measurement_reflns_used 4567 _cell_measurement_temperature 120.00(10) _cell_measurement_theta_max 73.3970 _cell_measurement_theta_min 6.5600 _cell_volume 1273.78(13) _computing_cell_refinement 'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)' _computing_data_collection 'CrysAlisPro 1.171.39.28b (Rigaku OD, 2015)' _computing_data_reduction 'CrysAlisPro 1.171.39.28b (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)' _computing_structure_solution 'ShelXT (Sheldrick, 2015)' _diffrn_ambient_environment N~2~ _diffrn_ambient_temperature 120.00(10) _diffrn_detector 'CCD plate' _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _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 -62.00 -37.00 0.50 0.50 -- 0.00 -56.00 44.00 50 2 \w 18.00 43.00 0.50 0.50 -- 5.00 56.00-173.00 50 3 \w -57.00 -32.00 0.50 0.50 -- 5.00 -56.00 44.00 50 4 \w -141.00-116.00 0.50 0.50 -- -98.80 -56.00 44.00 50 5 \w -111.00 -60.00 0.50 0.50 -- -98.80 56.00-173.00 102 6 \w -41.00 9.00 0.50 0.50 -- 0.00 -37.00 -30.00 100 7 \w -74.00 -47.00 0.50 0.50 -- 0.00 -37.00 -30.00 54 8 \w -41.00 7.00 0.50 0.50 -- 0.00 -72.00 150.00 96 9 \w -85.00 -45.00 0.50 0.50 -- 0.00 -72.00 150.00 80 10 \w -110.00 -85.00 0.50 0.50 -- -98.80 -19.00-180.00 50 11 \w -96.00 -46.00 0.50 0.50 -- -98.80 37.00 -30.00 100 12 \w -102.00 -10.00 0.50 0.50 -- -98.80 37.00-180.00 184 13 \w -176.00-151.00 0.50 0.50 -- -98.80 -19.00 120.00 50 14 \w -186.00 -89.00 0.50 0.50 -- -98.80 -57.00 60.00 194 15 \w -141.00 -86.00 0.50 0.50 -- -98.80 -19.00 120.00 110 16 \w -103.00 -32.00 0.50 0.50 -- -98.80 37.00 30.00 142 17 \w -105.00 -15.00 0.50 0.50 -- -98.80 19.00 0.00 180 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'XtaLAB AFC12 (RCD3): Kappa single' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 0.0016346000 _diffrn_orient_matrix_UB_12 0.0550449000 _diffrn_orient_matrix_UB_13 -0.1154898000 _diffrn_orient_matrix_UB_21 -0.0951904000 _diffrn_orient_matrix_UB_22 -0.1156919000 _diffrn_orient_matrix_UB_23 -0.0561240000 _diffrn_orient_matrix_UB_31 -0.0797555000 _diffrn_orient_matrix_UB_32 0.1409888000 _diffrn_orient_matrix_UB_33 -0.0009064000 _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0240 _diffrn_reflns_av_unetI/netI 0.0211 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.999 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -6 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_number 5898 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.999 _diffrn_reflns_theta_full 67.079 _diffrn_reflns_theta_max 67.079 _diffrn_reflns_theta_min 3.567 _diffrn_source 'fine-focus sealed X-ray tube' _diffrn_source_type 'Enhance (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 0.713 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.71569 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.39.28b (Rigaku Oxford Diffraction, 2015) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_density_diffrn 1.373 _exptl_crystal_description block _exptl_crystal_F_000 552 _exptl_crystal_size_max 0.07 _exptl_crystal_size_mid 0.05 _exptl_crystal_size_min 0.05 _refine_diff_density_max 0.256 _refine_diff_density_min -0.397 _refine_diff_density_rms 0.101 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.077 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 181 _refine_ls_number_reflns 2269 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.077 _refine_ls_R_factor_all 0.0450 _refine_ls_R_factor_gt 0.0437 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'w=1/[\s^2^(Fo^2^)+(0.0610P)^2^+0.3595P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1074 _refine_ls_wR_factor_ref 0.1083 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2151 _reflns_number_total 2269 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0py00193g2.cif _cod_data_source_block 1 _cod_depositor_comments ;Adding full bibliography for 1557775--1557777.cif. Adding full bibliography for 1557775--1557777.cif. ; _cod_original_cell_volume 1273.78(12) _cod_database_code 1557775 _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. ; _reflns_odcompleteness_completeness 99.88 _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 2.a Secondary CH2 refined with riding coordinates: C00C(H00C,H00D) 2.b Aromatic/amide H refined with riding coordinates: C009(H009), C00A(H00A), C00B(H00B), C00D(H00E), C00E(H00F), C00F(H00G), C00G(H00H), C00H(H00I), C00I(H00J), C00J(H00K), C00K(H00L) ; _shelx_res_file ; TITL 1_a.res in P2(1)/c 1.res created by SHELXL-2018/3 at 16:42:47 on 16-May-2019 REM Old TITL 1 in P2(1)/c REM SHELXT solution in P2(1)/c: R1 0.148, Rweak 0.038, Alpha 0.023 REM 0.827 for 194 systematic absences, Orientation as input REM Formula found by SHELXT: C17 N2 O CELL 1.54184 13.1254 8.1029 12.686 90 109.249 90 ZERR 4 0.0007 0.0004 0.0007 0 0.006 0 LATT 1 SYMM -X,0.5+Y,0.5-Z SFAC C H N O UNIT 64 52 12 4 L.S. 4 0 0 PLAN 20 BOND list 4 fmap 2 53 ACTA SHEL 999 0.837 REM REM REM WGHT 0.061000 0.359500 FVAR 0.75936 O001 4 0.729104 0.423633 0.719848 11.00000 0.03618 0.07278 = 0.02606 -0.01695 0.00925 -0.01076 N002 3 0.676559 0.428053 0.480759 11.00000 0.02436 0.02692 = 0.02260 0.00247 0.00703 0.00266 N003 3 0.539362 0.326224 0.354867 11.00000 0.02869 0.05162 = 0.01934 0.00460 0.00717 -0.00522 N004 3 0.629377 0.409590 0.371431 11.00000 0.03026 0.05349 = 0.02175 0.00772 0.00663 -0.00564 C005 1 0.432903 0.196133 0.457607 11.00000 0.02457 0.02288 = 0.02202 0.00102 0.00888 0.00605 C006 1 0.875838 0.401045 0.548199 11.00000 0.02446 0.02082 = 0.02899 0.00052 0.00852 -0.00453 C007 1 0.528170 0.289614 0.454827 11.00000 0.02497 0.02446 = 0.01742 0.00135 0.00758 0.00610 C008 1 0.616833 0.355359 0.537574 11.00000 0.02530 0.02390 = 0.02197 0.00012 0.00958 0.00376 C009 1 0.904010 0.325043 0.463447 11.00000 0.03187 0.02900 = 0.02477 0.00302 0.00988 -0.00349 AFIX 43 H009 2 0.862725 0.343261 0.389260 11.00000 -1.20000 AFIX 0 C00A 1 0.938165 0.371508 0.658514 11.00000 0.03125 0.03034 = 0.02649 -0.00355 0.00888 -0.00049 AFIX 43 H00A 2 0.920117 0.421376 0.715989 11.00000 -1.20000 AFIX 0 C00B 1 0.411390 0.159612 0.555534 11.00000 0.02829 0.03898 = 0.02238 0.00346 0.00878 0.00447 AFIX 43 H00B 2 0.458390 0.196232 0.623714 11.00000 -1.20000 AFIX 0 C00C 1 0.780321 0.516379 0.519724 11.00000 0.02760 0.02475 = 0.03418 0.00206 0.00921 -0.00139 AFIX 23 H00C 2 0.783856 0.580845 0.585265 11.00000 -1.20000 H00D 2 0.784169 0.592215 0.461994 11.00000 -1.20000 AFIX 0 C00D 1 1.054848 0.193928 0.598911 11.00000 0.02588 0.03006 = 0.04115 0.00469 0.01343 0.00255 AFIX 43 H00E 2 1.114772 0.125043 0.615862 11.00000 -1.20000 AFIX 0 C00E 1 1.026829 0.268433 0.683298 11.00000 0.03086 0.03626 = 0.02819 0.00264 0.00400 0.00131 AFIX 43 H00F 2 1.067937 0.249112 0.757399 11.00000 -1.20000 AFIX 0 C00F 1 0.992985 0.222641 0.488870 11.00000 0.03591 0.03111 = 0.03368 0.00016 0.01988 -0.00085 AFIX 43 H00G 2 1.011429 0.172678 0.431669 11.00000 -1.20000 AFIX 0 C00G 1 0.361063 0.138524 0.356916 11.00000 0.03571 0.03875 = 0.02367 -0.00481 0.01161 -0.00466 AFIX 43 H00H 2 0.374061 0.160557 0.290533 11.00000 -1.20000 AFIX 0 C00H 1 0.249856 0.014680 0.452490 11.00000 0.03086 0.02552 = 0.04877 0.00161 0.01857 0.00052 AFIX 43 H00I 2 0.188632 -0.044642 0.450637 11.00000 -1.20000 AFIX 0 C00I 1 0.320949 0.069531 0.552521 11.00000 0.03320 0.03569 = 0.03471 0.01065 0.01833 0.00793 AFIX 43 H00J 2 0.308005 0.045753 0.618701 11.00000 -1.20000 AFIX 0 C00J 1 0.270881 0.049159 0.354733 11.00000 0.03706 0.03998 = 0.03627 -0.01022 0.01068 -0.00928 AFIX 43 H00K 2 0.223721 0.011690 0.286884 11.00000 -1.20000 AFIX 0 C00K 1 0.648818 0.358302 0.658886 11.00000 0.04029 0.07303 = 0.02282 -0.00773 0.01191 -0.01745 AFIX 43 H00L 2 0.603907 0.305815 0.691795 11.00000 -1.20000 AFIX 0 HKLF 4 REM 1_a.res in P2(1)/c REM wR2 = 0.1083, GooF = S = 1.077, Restrained GooF = 1.077 for all data REM R1 = 0.0437 for 2151 Fo > 4sig(Fo) and 0.0450 for all 2269 data REM 181 parameters refined using 0 restraints END WGHT 0.0607 0.3615 REM Highest difference peak 0.256, deepest hole -0.397, 1-sigma level 0.101 Q1 1 0.4804 0.3873 0.6887 11.00000 0.05 0.26 Q2 1 0.4994 0.1016 0.2733 11.00000 0.05 0.25 Q3 1 0.5670 0.3911 0.6921 11.00000 0.05 0.25 Q4 1 0.6311 0.2191 0.6985 11.00000 0.05 0.25 Q5 1 0.7676 0.2767 0.8031 11.00000 0.05 0.24 Q6 1 0.5115 0.4586 0.7259 11.00000 0.05 0.24 Q7 1 0.2760 0.3017 0.2259 11.00000 0.05 0.23 Q8 1 0.4276 0.0799 0.2855 11.00000 0.05 0.21 Q9 1 0.6793 0.3344 0.2803 11.00000 0.05 0.21 Q10 1 0.7025 0.3024 0.3009 11.00000 0.05 0.20 Q11 1 0.9902 0.5427 0.7270 11.00000 0.05 0.19 Q12 1 0.0771 -0.0355 0.2817 11.00000 0.05 0.19 Q13 1 0.8258 0.3017 0.7343 11.00000 0.05 0.19 Q14 1 1.1269 0.3101 0.7702 11.00000 0.05 0.19 Q15 1 0.3010 0.1387 0.6560 11.00000 0.05 0.18 Q16 1 0.4772 0.3643 0.6279 11.00000 0.05 0.18 Q17 1 0.8027 0.2637 0.2684 11.00000 0.05 0.18 Q18 1 0.2220 -0.1649 0.2529 11.00000 0.05 0.18 Q19 1 0.9838 0.1032 0.7054 11.00000 0.05 0.18 Q20 1 0.1854 -0.1823 0.3110 11.00000 0.05 0.18 ; _shelx_res_checksum 16681 _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 1.335 _oxdiff_exptl_absorpt_empirical_full_min 0.659 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 O001 O 0.72910(8) 0.42363(15) 0.71985(8) 0.0453(3) Uani 1 1 d . . . . . N002 N 0.67656(8) 0.42805(13) 0.48076(8) 0.0248(3) Uani 1 1 d . . . . . N003 N 0.53936(9) 0.32622(16) 0.35487(9) 0.0334(3) Uani 1 1 d . . . . . N004 N 0.62938(9) 0.40959(16) 0.37143(9) 0.0356(3) Uani 1 1 d . . . . . C005 C 0.43290(9) 0.19613(15) 0.45761(10) 0.0229(3) Uani 1 1 d . . . . . C006 C 0.87584(10) 0.40105(15) 0.54820(10) 0.0248(3) Uani 1 1 d . . . . . C007 C 0.52817(9) 0.28961(15) 0.45483(9) 0.0221(3) Uani 1 1 d . . . . . C008 C 0.61683(10) 0.35536(15) 0.53757(10) 0.0233(3) Uani 1 1 d . . . . . C009 C 0.90401(11) 0.32504(16) 0.46345(11) 0.0284(3) Uani 1 1 d . . . . . H009 H 0.862725 0.343261 0.389260 0.034 Uiso 1 1 calc R . . . . C00A C 0.93816(10) 0.37151(16) 0.65851(11) 0.0295(3) Uani 1 1 d . . . . . H00A H 0.920117 0.421376 0.715989 0.035 Uiso 1 1 calc R . . . . C00B C 0.41139(10) 0.15961(17) 0.55553(11) 0.0298(3) Uani 1 1 d . . . . . H00B H 0.458390 0.196232 0.623714 0.036 Uiso 1 1 calc R . . . . C00C C 0.78032(10) 0.51638(16) 0.51972(11) 0.0291(3) Uani 1 1 d . . . . . H00C H 0.783856 0.580845 0.585265 0.035 Uiso 1 1 calc R . . . . H00D H 0.784169 0.592215 0.461994 0.035 Uiso 1 1 calc R . . . . C00D C 1.05485(10) 0.19393(17) 0.59891(12) 0.0318(3) Uani 1 1 d . . . . . H00E H 1.114772 0.125043 0.615862 0.038 Uiso 1 1 calc R . . . . C00E C 1.02683(11) 0.26843(17) 0.68330(11) 0.0332(3) Uani 1 1 d . . . . . H00F H 1.067937 0.249112 0.757399 0.040 Uiso 1 1 calc R . . . . C00F C 0.99298(11) 0.22264(17) 0.48887(12) 0.0315(3) Uani 1 1 d . . . . . H00G H 1.011429 0.172678 0.431669 0.038 Uiso 1 1 calc R . . . . C00G C 0.36106(11) 0.13852(17) 0.35692(11) 0.0323(3) Uani 1 1 d . . . . . H00H H 0.374061 0.160557 0.290533 0.039 Uiso 1 1 calc R . . . . C00H C 0.24986(11) 0.01468(17) 0.45249(12) 0.0337(3) Uani 1 1 d . . . . . H00I H 0.188632 -0.044642 0.450637 0.040 Uiso 1 1 calc R . . . . C00I C 0.32095(11) 0.06953(17) 0.55252(12) 0.0328(3) Uani 1 1 d . . . . . H00J H 0.308005 0.045753 0.618701 0.039 Uiso 1 1 calc R . . . . C00J C 0.27088(12) 0.04916(19) 0.35473(12) 0.0381(3) Uani 1 1 d . . . . . H00K H 0.223721 0.011690 0.286884 0.046 Uiso 1 1 calc R . . . . C00K C 0.64882(12) 0.3583(2) 0.65889(12) 0.0450(4) Uani 1 1 d . . . . . H00L H 0.603907 0.305815 0.691795 0.054 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 O001 0.0362(6) 0.0728(8) 0.0261(5) -0.0169(5) 0.0093(4) -0.0108(5) N002 0.0244(5) 0.0269(6) 0.0226(5) 0.0025(4) 0.0070(4) 0.0027(4) N003 0.0287(6) 0.0516(7) 0.0193(5) 0.0046(5) 0.0072(4) -0.0052(5) N004 0.0303(6) 0.0535(7) 0.0217(6) 0.0077(5) 0.0066(5) -0.0056(5) C005 0.0246(6) 0.0229(6) 0.0220(6) 0.0010(5) 0.0089(5) 0.0060(5) C006 0.0245(6) 0.0208(6) 0.0290(7) 0.0005(5) 0.0085(5) -0.0045(5) C007 0.0250(6) 0.0245(6) 0.0174(6) 0.0014(5) 0.0076(5) 0.0061(5) C008 0.0253(6) 0.0239(6) 0.0220(6) 0.0001(5) 0.0096(5) 0.0038(5) C009 0.0319(7) 0.0290(7) 0.0248(6) 0.0030(5) 0.0099(5) -0.0035(5) C00A 0.0313(7) 0.0303(7) 0.0265(7) -0.0036(5) 0.0089(5) -0.0005(5) C00B 0.0283(7) 0.0390(7) 0.0224(6) 0.0035(5) 0.0088(5) 0.0045(5) C00C 0.0276(7) 0.0247(6) 0.0342(7) 0.0021(5) 0.0092(6) -0.0014(5) C00D 0.0259(6) 0.0301(7) 0.0411(8) 0.0047(6) 0.0134(6) 0.0025(5) C00E 0.0309(7) 0.0363(7) 0.0282(7) 0.0026(6) 0.0040(5) 0.0013(6) C00F 0.0359(7) 0.0311(7) 0.0337(7) 0.0002(6) 0.0199(6) -0.0009(6) C00G 0.0357(7) 0.0388(7) 0.0237(7) -0.0048(5) 0.0116(6) -0.0047(6) C00H 0.0309(7) 0.0255(7) 0.0488(8) 0.0016(6) 0.0186(6) 0.0005(5) C00I 0.0332(7) 0.0357(7) 0.0347(7) 0.0106(6) 0.0183(6) 0.0079(6) C00J 0.0371(8) 0.0400(8) 0.0363(8) -0.0102(6) 0.0107(6) -0.0093(6) C00K 0.0403(8) 0.0730(11) 0.0228(7) -0.0077(7) 0.0119(6) -0.0175(8) 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 N004 N002 C008 110.64(10) . . ? N004 N002 C00C 117.82(10) . . ? C008 N002 C00C 131.52(10) . . ? N004 N003 C007 109.33(10) . . ? N003 N004 N002 108.03(10) . . ? C00B C005 C007 123.64(11) . . ? C00B C005 C00G 118.10(12) . . ? C00G C005 C007 118.26(11) . . ? C009 C006 C00C 120.06(11) . . ? C00A C006 C009 118.96(12) . . ? C00A C006 C00C 120.98(12) . . ? N003 C007 C005 119.30(11) . . ? N003 C007 C008 107.47(11) . . ? C008 C007 C005 133.23(11) . . ? N002 C008 C007 104.52(10) . . ? N002 C008 C00K 122.47(12) . . ? C007 C008 C00K 133.01(12) . . ? C00F C009 C006 120.35(12) . . ? C00E C00A C006 120.36(12) . . ? C00I C00B C005 120.78(12) . . ? N002 C00C C006 112.51(10) . . ? C00E C00D C00F 119.41(12) . . ? C00D C00E C00A 120.50(12) . . ? C009 C00F C00D 120.42(13) . . ? C00J C00G C005 120.70(12) . . ? C00I C00H C00J 119.04(13) . . ? C00H C00I C00B 120.68(12) . . ? C00G C00J C00H 120.71(13) . . ? O001 C00K C008 124.90(14) . . ? 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 O001 C00K 1.2048(18) . ? N002 N004 1.3278(15) . ? N002 C008 1.3614(16) . ? N002 C00C 1.4722(16) . ? N003 N004 1.3163(16) . ? N003 C007 1.3566(15) . ? C005 C007 1.4723(17) . ? C005 C00B 1.3935(17) . ? C005 C00G 1.3945(18) . ? C006 C009 1.3907(18) . ? C006 C00A 1.3893(18) . ? C006 C00C 1.5090(17) . ? C007 C008 1.3909(17) . ? C008 C00K 1.4558(18) . ? C009 C00F 1.3813(19) . ? C00A C00E 1.3818(19) . ? C00B C00I 1.3833(19) . ? C00D C00E 1.380(2) . ? C00D C00F 1.384(2) . ? C00G C00J 1.380(2) . ? C00H C00I 1.378(2) . ? C00H C00J 1.385(2) . ?