#------------------------------------------------------------------------------ #$Date: 2020-10-06 14:42:41 +0300 (Tue, 06 Oct 2020) $ #$Revision: 258104 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/05/7240542.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_7240542 loop_ _publ_author_name 'Aksenov, Nicolai A.' 'Aksenov, Dmitrii A.' 'Arutiunov, Nikolai A.' 'Aksenova, Daria S.' 'Aksenov, Alexander V.' 'Rubin, Michael' _publ_section_title ; Unexpected cyclization of ortho-nitrochalcones into 2-alkylideneindolin-3-ones ; _journal_issue 31 _journal_name_full 'RSC Advances' _journal_page_first 18440 _journal_page_last 18450 _journal_paper_doi 10.1039/D0RA03520C _journal_volume 10 _journal_year 2020 _chemical_formula_moiety 'C18 H14 N2 O' _chemical_formula_sum 'C18 H14 N2 O' _chemical_formula_weight 274.31 _chemical_name_systematic (E)-2-(4-ethylphenyl)-2-(3-oxoindolin-2-ylidene)acetonitrile _space_group_crystal_system monoclinic _space_group_IT_number 15 _space_group_name_Hall '-C 2yc' _space_group_name_H-M_alt 'C 1 2/c 1' _atom_sites_solution_hydrogens mixed _atom_sites_solution_primary dual _audit_creation_date 2020-03-24 _audit_creation_method ; Olex2 1.2 (compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) ; _audit_update_record ; 2020-03-24 deposited with the CCDC. 2020-05-08 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 102.8320(10) _cell_angle_gamma 90 _cell_formula_units_Z 8 _cell_length_a 20.6798(2) _cell_length_b 11.21770(10) _cell_length_c 12.58050(10) _cell_measurement_reflns_used 10550 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 76.1480 _cell_measurement_theta_min 4.3530 _cell_volume 2845.54(5) _computing_cell_refinement 'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)' _computing_data_collection 'CrysAlisPro 1.171.39.46 (Rigaku OD, 2018)' _computing_data_reduction 'CrysAlisPro 1.171.39.46 (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 5.2529 _diffrn_detector_type AtlasS2 _diffrn_measured_fraction_theta_full 1.000 _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 -116.00 -17.00 1.00 2.63 -- -41.72 -38.00-150.00 99 2 \w -87.00 -6.00 1.00 2.63 -- -41.72 125.00 150.00 81 3 \w 6.00 83.00 1.00 2.63 -- 41.72 -99.00 90.00 77 4 \w 8.00 42.00 1.00 2.63 -- 41.72 81.00 -41.72 34 5 \w 30.00 106.00 1.00 10.53 -- 112.00 -95.00 30.00 76 6 \w 86.00 178.00 1.00 10.53 -- 112.00 45.00-150.00 92 7 \w 86.00 178.00 1.00 10.53 -- 112.00 45.00-120.00 92 8 \w 61.00 146.00 1.00 10.53 -- 112.00 178.00 0.00 85 9 \w 104.00 178.00 1.00 10.53 -- 112.00 111.00 -30.00 74 10 \w 36.00 109.00 1.00 10.53 -- 112.00-111.00 0.00 73 11 \w 30.00 106.00 1.00 10.53 -- 112.00 -95.00 0.00 76 12 \w 36.00 109.00 1.00 10.53 -- 112.00-111.00 -30.00 73 13 \w 40.00 141.00 1.00 10.53 -- 112.00 -61.00 0.00 101 14 \w 40.00 141.00 1.00 10.53 -- 112.00 -61.00 60.00 101 15 \w 103.00 178.00 1.00 10.53 -- 112.00 77.00 120.00 75 16 \w 104.00 178.00 1.00 10.53 -- 112.00 111.00 30.00 74 17 \w 36.00 140.00 1.00 10.53 -- 112.00 -30.00-150.00 104 18 \w 104.00 178.00 1.00 10.53 -- 112.00 111.00 150.00 74 19 \w 86.00 178.00 1.00 10.53 -- 112.00 45.00 120.00 92 20 \w 37.00 144.00 1.00 10.53 -- 112.00 -74.00 -73.03 107 21 \w -114.00 -42.00 1.00 2.63 -- -41.72 -57.00 120.00 72 22 \w 8.00 42.00 1.00 2.63 -- 41.72 82.00 74.19 34 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'SuperNova, Dual, Cu at home/near, AtlasS2' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 -0.0124894000 _diffrn_orient_matrix_UB_12 -0.1325839000 _diffrn_orient_matrix_UB_13 0.0202701000 _diffrn_orient_matrix_UB_21 0.0743605000 _diffrn_orient_matrix_UB_22 -0.0170833000 _diffrn_orient_matrix_UB_23 0.0508493000 _diffrn_orient_matrix_UB_31 -0.0123512000 _diffrn_orient_matrix_UB_32 0.0314582000 _diffrn_orient_matrix_UB_33 0.1130357000 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0160 _diffrn_reflns_av_unetI/netI 0.0101 _diffrn_reflns_Laue_measured_fraction_full 1.000 _diffrn_reflns_Laue_measured_fraction_max 0.999 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_h_min -26 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_number 15274 _diffrn_reflns_point_group_measured_fraction_full 1.000 _diffrn_reflns_point_group_measured_fraction_max 0.999 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 76.345 _diffrn_reflns_theta_min 4.386 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'SuperNova (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 0.640 _exptl_absorpt_correction_T_max 0.982 _exptl_absorpt_correction_T_min 0.950 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details ; CrysAlisPro 1.171.39.46 (Rigaku Oxford Diffraction, 2018) Analytical numeric absorption correction using a multifaceted crystal model based on expressions derived by R.C. Clark & J.S. Reid. (Clark, R. C. & Reid, J. S. (1995). Acta Cryst. A51, 887-897) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour 'clear reddish red' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier reddish _exptl_crystal_colour_primary red _exptl_crystal_density_diffrn 1.281 _exptl_crystal_description block _exptl_crystal_F_000 1152 _exptl_crystal_size_max 0.394 _exptl_crystal_size_mid 0.208 _exptl_crystal_size_min 0.107 _refine_diff_density_max 0.198 _refine_diff_density_min -0.164 _refine_diff_density_rms 0.034 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.045 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 195 _refine_ls_number_reflns 2976 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.045 _refine_ls_R_factor_all 0.0408 _refine_ls_R_factor_gt 0.0390 _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^)+(0.0609P)^2^+0.9312P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1083 _refine_ls_wR_factor_ref 0.1106 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2786 _reflns_number_total 2976 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d0ra03520c2.cif _cod_data_source_block anna1120_isat(da_final)_3 _cod_depositor_comments 'Adding full bibliography for 7240542.cif.' _cod_original_cell_volume 2845.53(5) _cod_database_code 7240542 _shelx_shelxl_version_number 2018/3 _chemical_oxdiff_formula 'C11 H10 N O' _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 98.46 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 77.17 _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: C17(H17A,H17B) 2.b Aromatic/amide H refined with riding coordinates: C16(H16), C15(H15), C12(H12), C7(H7), C13(H13), C4(H4), C6(H6), C5(H5) 2.c Idealised Me refined as rotating group: C18(H18A,H18B,H18C) ; _shelx_res_file ; TITL anna1120_isat(da_final)_3_a.res in C2/c anna1120_isat(da_final)_3.res created by SHELXL-2018/3 at 21:07:07 on 24-Mar-2020 REM Old TITL anna1120_isat(da_final)_3_a.res in C2/c REM SHELXT solution in C2/c: R1 0.151, Rweak 0.016, Alpha 0.026 REM 0.686 for 155 systematic absences, Orientation as input REM Formula found by SHELXT: C18 N2 O CELL 1.54184 20.6798 11.2177 12.5805 90 102.832 90 ZERR 8 0.0002 0.0001 0.0001 0 0.001 0 LATT 7 SYMM -X,+Y,0.5-Z SFAC C H N O UNIT 144 112 16 8 EQIV $1 +X,1-Y,0.5+Z L.S. 22 PLAN 20 HTAB N1 O1_$1 BOND list 4 fmap 2 53 acta OMIT 5 1 1 REM REM REM WGHT 0.060900 0.931200 FVAR 2.54657 O1 4 0.412368 0.462014 0.273778 11.00000 0.08356 0.05997 = 0.02897 -0.00165 0.01900 -0.00285 N1 3 0.406394 0.515827 0.544587 11.00000 0.06928 0.04065 = 0.02738 -0.00082 0.01603 -0.00390 C8 1 0.426006 0.626672 0.513545 11.00000 0.04589 0.04239 = 0.03523 0.00026 0.00974 -0.00107 C1 1 0.398946 0.436094 0.459929 11.00000 0.05181 0.04221 = 0.02634 0.00059 0.01058 0.00190 C2 1 0.414861 0.503452 0.364384 11.00000 0.04885 0.04759 = 0.02801 0.00265 0.01015 0.00036 C9 1 0.378569 0.321179 0.459001 11.00000 0.05169 0.04109 = 0.03060 -0.00057 0.00980 0.00192 C11 1 0.352452 0.261916 0.545873 11.00000 0.05082 0.03760 = 0.03327 0.00197 0.00882 0.00081 N2 3 0.385356 0.179513 0.300999 11.00000 0.09580 0.05857 = 0.05336 -0.01833 0.02997 -0.01539 C3 1 0.430323 0.624099 0.404380 11.00000 0.04506 0.04792 = 0.03370 0.00272 0.00959 -0.00379 C16 1 0.315183 0.324774 0.606704 11.00000 0.05421 0.03445 = 0.04557 0.00436 0.01537 0.00291 AFIX 43 H16 2 0.307437 0.405721 0.593831 11.00000 -1.20000 AFIX 0 C14 1 0.299755 0.147462 0.707537 11.00000 0.05665 0.04088 = 0.04300 0.00479 0.01233 -0.00485 C10 1 0.382653 0.247353 0.367521 11.00000 0.06108 0.04641 = 0.03762 -0.00371 0.01427 -0.00572 C15 1 0.289561 0.268402 0.685955 11.00000 0.05482 0.04146 = 0.04986 0.00188 0.02074 0.00118 AFIX 43 H15 2 0.264960 0.312313 0.725729 11.00000 -1.20000 AFIX 0 C12 1 0.361511 0.140163 0.565576 11.00000 0.07120 0.03877 = 0.04659 0.00053 0.02059 0.00762 AFIX 43 H12 2 0.385154 0.095758 0.524599 11.00000 -1.20000 AFIX 0 C7 1 0.438876 0.729528 0.575207 11.00000 0.06185 0.04860 = 0.04639 -0.00770 0.01136 -0.00465 AFIX 43 H7 2 0.436961 0.730890 0.648358 11.00000 -1.20000 AFIX 0 C13 1 0.335859 0.084443 0.645152 11.00000 0.07758 0.03436 = 0.05213 0.00622 0.01906 0.00400 AFIX 43 H13 2 0.342883 0.003200 0.657210 11.00000 -1.20000 AFIX 0 C4 1 0.445856 0.726862 0.353290 11.00000 0.05868 0.06087 = 0.04662 0.00992 0.01233 -0.01416 AFIX 43 H4 2 0.448140 0.725854 0.280296 11.00000 -1.20000 AFIX 0 C6 1 0.454705 0.830110 0.523040 11.00000 0.07052 0.04750 = 0.06965 -0.00743 0.00785 -0.01328 AFIX 43 H6 2 0.463670 0.900574 0.562515 11.00000 -1.20000 AFIX 0 C17 1 0.271955 0.084439 0.794010 11.00000 0.07883 0.05146 = 0.05821 0.00884 0.02578 -0.00953 AFIX 23 H17A 2 0.229392 0.050311 0.759360 11.00000 -1.20000 H17B 2 0.301333 0.018936 0.822524 11.00000 -1.20000 AFIX 0 C5 1 0.457751 0.830068 0.413734 11.00000 0.07423 0.05431 = 0.06958 0.01033 0.01134 -0.02214 AFIX 43 H5 2 0.467870 0.900072 0.381298 11.00000 -1.20000 AFIX 0 C18 1 0.262588 0.159514 0.888256 11.00000 0.09972 0.07461 = 0.05609 0.00628 0.03409 -0.01397 AFIX 137 H18A 2 0.227640 0.216034 0.863428 11.00000 -1.50000 H18B 2 0.303009 0.201244 0.918552 11.00000 -1.50000 H18C 2 0.251126 0.109263 0.943045 11.00000 -1.50000 AFIX 0 H1 2 0.404668 0.500814 0.611687 11.00000 0.05693 HKLF 4 REM anna1120_isat(da_final)_3_a.res in C2/c REM wR2 = 0.1106, GooF = S = 1.045, Restrained GooF = 1.045 for all data REM R1 = 0.0390 for 2786 Fo > 4sig(Fo) and 0.0408 for all 2976 data REM 195 parameters refined using 0 restraints END WGHT 0.0609 0.9312 REM Highest difference peak 0.198, deepest hole -0.164, 1-sigma level 0.034 Q1 1 0.4339 0.6220 0.4614 11.00000 0.05 0.20 Q2 1 0.3656 0.2928 0.4957 11.00000 0.05 0.18 Q3 1 0.4022 0.4627 0.4100 11.00000 0.05 0.17 Q4 1 0.5000 1.0262 0.2500 10.50000 0.05 0.16 Q5 1 0.3001 0.2074 0.7023 11.00000 0.05 0.14 Q6 1 0.4770 0.7758 0.3956 11.00000 0.05 0.13 Q7 1 0.4269 0.5719 0.3785 11.00000 0.05 0.13 Q8 1 0.2636 -0.0005 0.7778 11.00000 0.05 0.13 Q9 1 0.2824 0.1178 0.7419 11.00000 0.05 0.12 Q10 1 0.2768 0.2432 0.9047 11.00000 0.05 0.12 Q11 1 0.3186 0.3011 0.6680 11.00000 0.05 0.12 Q12 1 0.3244 0.2874 0.5526 11.00000 0.05 0.11 Q13 1 0.3814 0.2854 0.4140 11.00000 0.05 0.10 Q14 1 0.3425 0.1993 0.5366 11.00000 0.05 0.10 Q15 1 0.3200 0.1195 0.6775 11.00000 0.05 0.10 Q16 1 0.3767 0.0042 0.6949 11.00000 0.05 0.10 Q17 1 0.4263 0.6787 0.5382 11.00000 0.05 0.10 Q18 1 0.3019 0.2864 0.6350 11.00000 0.05 0.10 Q19 1 0.3044 0.0987 0.8698 11.00000 0.05 0.10 Q20 1 0.4736 0.8127 0.4785 11.00000 0.05 0.10 ; _shelx_res_checksum 31390 _olex2_exptl_crystal_mounting_method 'Mounted by acrylic glue on the glass stick' _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 1.399 _oxdiff_exptl_absorpt_empirical_full_min 0.603 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, y, -z+1/2' 'x+1/2, y+1/2, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -z' 'x, -y, z-1/2' '-x+1/2, -y+1/2, -z' 'x+1/2, -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 O1 O 0.41237(5) 0.46201(9) 0.27378(6) 0.0565(2) Uani 1 1 d . . . . . N1 N 0.40639(5) 0.51583(9) 0.54459(7) 0.0449(2) Uani 1 1 d . . . . . C8 C 0.42601(5) 0.62667(10) 0.51354(8) 0.0411(2) Uani 1 1 d . . . . . C1 C 0.39895(5) 0.43609(10) 0.45993(8) 0.0398(2) Uani 1 1 d . . . . . C2 C 0.41486(5) 0.50345(10) 0.36438(8) 0.0412(2) Uani 1 1 d . . . . . C9 C 0.37857(6) 0.32118(10) 0.45900(8) 0.0410(2) Uani 1 1 d . . . . . C11 C 0.35245(5) 0.26192(10) 0.54587(8) 0.0406(2) Uani 1 1 d . . . . . N2 N 0.38536(7) 0.17951(11) 0.30100(9) 0.0672(3) Uani 1 1 d . . . . . C3 C 0.43032(5) 0.62410(10) 0.40438(8) 0.0421(2) Uani 1 1 d . . . . . C16 C 0.31518(6) 0.32477(10) 0.60670(9) 0.0441(3) Uani 1 1 d . . . . . H16 H 0.307437 0.405721 0.593831 0.053 Uiso 1 1 calc R . . . . C14 C 0.29976(6) 0.14746(10) 0.70754(9) 0.0466(3) Uani 1 1 d . . . . . C10 C 0.38265(6) 0.24735(11) 0.36752(9) 0.0479(3) Uani 1 1 d . . . . . C15 C 0.28956(6) 0.26840(11) 0.68595(10) 0.0473(3) Uani 1 1 d . . . . . H15 H 0.264960 0.312313 0.725729 0.057 Uiso 1 1 calc R . . . . C12 C 0.36151(7) 0.14016(11) 0.56558(10) 0.0510(3) Uani 1 1 d . . . . . H12 H 0.385154 0.095758 0.524599 0.061 Uiso 1 1 calc R . . . . C7 C 0.43888(7) 0.72953(11) 0.57521(10) 0.0524(3) Uani 1 1 d . . . . . H7 H 0.436961 0.730890 0.648358 0.063 Uiso 1 1 calc R . . . . C13 C 0.33586(7) 0.08444(11) 0.64515(10) 0.0540(3) Uani 1 1 d . . . . . H13 H 0.342883 0.003200 0.657210 0.065 Uiso 1 1 calc R . . . . C4 C 0.44586(7) 0.72686(12) 0.35329(11) 0.0553(3) Uani 1 1 d . . . . . H4 H 0.448140 0.725854 0.280296 0.066 Uiso 1 1 calc R . . . . C6 C 0.45470(8) 0.83011(13) 0.52304(13) 0.0638(4) Uani 1 1 d . . . . . H6 H 0.463670 0.900574 0.562515 0.077 Uiso 1 1 calc R . . . . C17 C 0.27196(8) 0.08444(13) 0.79401(12) 0.0612(3) Uani 1 1 d . . . . . H17A H 0.229392 0.050311 0.759360 0.073 Uiso 1 1 calc R . . . . H17B H 0.301333 0.018936 0.822524 0.073 Uiso 1 1 calc R . . . . C5 C 0.45775(8) 0.83007(13) 0.41373(13) 0.0668(4) Uani 1 1 d . . . . . H5 H 0.467870 0.900072 0.381298 0.080 Uiso 1 1 calc R . . . . C18 C 0.26259(10) 0.15951(16) 0.88826(13) 0.0742(4) Uani 1 1 d . . . . . H18A H 0.227640 0.216034 0.863428 0.111 Uiso 1 1 calc GR . . . . H18B H 0.303009 0.201244 0.918552 0.111 Uiso 1 1 calc GR . . . . H18C H 0.251126 0.109263 0.943045 0.111 Uiso 1 1 calc GR . . . . H1 H 0.4047(7) 0.5008(14) 0.6117(13) 0.057(4) Uiso 1 1 d . . . . . 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 O1 0.0836(6) 0.0600(5) 0.0290(4) -0.0017(3) 0.0190(4) -0.0028(4) N1 0.0693(6) 0.0407(5) 0.0274(4) -0.0008(3) 0.0160(4) -0.0039(4) C8 0.0459(5) 0.0424(6) 0.0352(5) 0.0003(4) 0.0097(4) -0.0011(4) C1 0.0518(6) 0.0422(5) 0.0263(4) 0.0006(4) 0.0106(4) 0.0019(4) C2 0.0488(6) 0.0476(6) 0.0280(5) 0.0027(4) 0.0101(4) 0.0004(4) C9 0.0517(6) 0.0411(5) 0.0306(5) -0.0006(4) 0.0098(4) 0.0019(4) C11 0.0508(6) 0.0376(5) 0.0333(5) 0.0020(4) 0.0088(4) 0.0008(4) N2 0.0958(9) 0.0586(7) 0.0534(6) -0.0183(5) 0.0300(6) -0.0154(6) C3 0.0451(5) 0.0479(6) 0.0337(5) 0.0027(4) 0.0096(4) -0.0038(4) C16 0.0542(6) 0.0344(5) 0.0456(6) 0.0044(4) 0.0154(5) 0.0029(4) C14 0.0566(6) 0.0409(6) 0.0430(6) 0.0048(4) 0.0123(5) -0.0048(5) C10 0.0611(7) 0.0464(6) 0.0376(5) -0.0037(5) 0.0143(5) -0.0057(5) C15 0.0548(6) 0.0415(6) 0.0499(6) 0.0019(5) 0.0207(5) 0.0012(5) C12 0.0712(8) 0.0388(6) 0.0466(6) 0.0005(5) 0.0206(5) 0.0076(5) C7 0.0619(7) 0.0486(7) 0.0464(6) -0.0077(5) 0.0114(5) -0.0046(5) C13 0.0776(8) 0.0344(6) 0.0521(7) 0.0062(5) 0.0191(6) 0.0040(5) C4 0.0587(7) 0.0609(8) 0.0466(6) 0.0099(5) 0.0123(5) -0.0142(6) C6 0.0705(8) 0.0475(7) 0.0697(9) -0.0074(6) 0.0079(7) -0.0133(6) C17 0.0788(9) 0.0515(7) 0.0582(7) 0.0088(6) 0.0258(7) -0.0095(6) C5 0.0742(9) 0.0543(8) 0.0696(9) 0.0103(7) 0.0113(7) -0.0221(7) C18 0.0997(12) 0.0746(10) 0.0561(8) 0.0063(7) 0.0341(8) -0.0140(9) 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_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 1 0 8 0.1497 12 -3 0 0.0794 -7 -1 8 0.2002 5 7 1 0.0567 6 -1 -8 0.1739 3 7 0 0.0581 -3 -7 0 0.0444 -5 7 0 0.0559 -9 -5 0 0.0589 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 C1 N1 C8 110.74(9) . . ? N1 C8 C3 110.13(9) . . ? C7 C8 N1 128.34(10) . . ? C7 C8 C3 121.51(11) . . ? N1 C1 C2 106.47(9) . . ? C9 C1 N1 127.40(9) . . ? C9 C1 C2 126.07(9) . . ? O1 C2 C1 125.34(11) . . ? O1 C2 C3 129.60(10) . . ? C3 C2 C1 105.02(8) . . ? C1 C9 C11 125.77(9) . . ? C1 C9 C10 118.82(10) . . ? C10 C9 C11 115.40(10) . . ? C16 C11 C9 121.05(10) . . ? C16 C11 C12 117.88(10) . . ? C12 C11 C9 121.00(10) . . ? C8 C3 C2 107.60(9) . . ? C4 C3 C8 120.59(11) . . ? C4 C3 C2 131.80(10) . . ? C15 C16 C11 120.84(10) . . ? C15 C14 C13 117.58(11) . . ? C15 C14 C17 122.05(11) . . ? C13 C14 C17 120.36(11) . . ? N2 C10 C9 173.42(13) . . ? C16 C15 C14 121.44(11) . . ? C13 C12 C11 120.94(11) . . ? C6 C7 C8 116.85(12) . . ? C12 C13 C14 121.30(11) . . ? C5 C4 C3 118.21(12) . . ? C7 C6 C5 122.51(13) . . ? C18 C17 C14 116.21(12) . . ? C4 C5 C6 120.31(12) . . ? 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 O1 C2 1.2214(13) . ? N1 C8 1.3905(14) . ? N1 C1 1.3730(13) . ? C8 C3 1.3962(14) . ? C8 C7 1.3828(16) . ? C1 C2 1.5165(14) . ? C1 C9 1.3554(16) . ? C2 C3 1.4545(16) . ? C9 C11 1.4800(14) . ? C9 C10 1.4355(15) . ? C11 C16 1.3924(15) . ? C11 C12 1.3933(16) . ? N2 C10 1.1417(16) . ? C3 C4 1.3917(16) . ? C16 C15 1.3818(15) . ? C14 C15 1.3904(17) . ? C14 C13 1.3905(18) . ? C14 C17 1.5138(16) . ? C12 C13 1.3821(17) . ? C7 C6 1.3807(19) . ? C4 C5 1.377(2) . ? C6 C5 1.390(2) . ? C17 C18 1.502(2) . ? loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A _geom_hbond_publ_flag N1 H1 O1 0.869(16) 2.053(16) 2.8692(12) 156.1(14) 6_566 yes loop_ _exptl_oxdiff_crystal_face_indexfrac_h _exptl_oxdiff_crystal_face_indexfrac_k _exptl_oxdiff_crystal_face_indexfrac_l _exptl_oxdiff_crystal_face_x _exptl_oxdiff_crystal_face_y _exptl_oxdiff_crystal_face_z 1.1585 0.2325 7.7719 0.1122 0.4774 0.8715 11.9560 -2.7998 0.3121 0.2282 0.9528 -0.2005 -6.9268 -0.5304 7.7318 0.3136 -0.1129 0.9428 5.3382 6.5430 0.7604 -0.9188 0.3238 0.2259 5.6406 -1.0313 -7.8988 -0.0938 0.0354 -0.9950 3.1931 7.0494 0.2017 -0.9704 0.1273 0.2051 -3.3364 -7.0415 -0.0008 0.9752 -0.1278 -0.1804 -4.7845 6.7979 0.3698 -0.8340 -0.4531 0.3147 -9.4562 -5.0697 0.1723 0.7938 -0.6078 -0.0232