#------------------------------------------------------------------------------ #$Date: 2019-11-11 20:30:12 +0200 (Mon, 11 Nov 2019) $ #$Revision: 227276 $ #$URL: file:///home/coder/svn-repositories/cod/cif/4/03/58/4035864.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_4035864 loop_ _publ_author_name 'Bookser, Brett C.' 'Weinhouse, Michael I.' 'Burns, Aaron C.' 'Valiere, Andrew N.' 'Valdez, Lino J.' 'Stanczak, Pawel' 'Na, Jim' 'Rheingold, Arnold L.' 'Moore, Curtis E.' 'Dyck, Brian' _publ_section_title ; Solvent-Controlled, Site-Selective N-Alkylation Reactions of Azolo-Fused Ring Heterocycles at N1-, N2-, and N3-Positions, Including Pyrazolo[3,4- d]pyrimidines, Purines, [1,2,3]Triazolo[4,5]pyridines, and Related Deaza-Compounds. ; _journal_issue 12 _journal_name_full 'The Journal of organic chemistry' _journal_page_first 6334 _journal_page_last 6353 _journal_paper_doi 10.1021/acs.joc.8b00540 _journal_volume 83 _journal_year 2018 _chemical_formula_moiety 'C7 H8 N4 O' _chemical_formula_sum 'C7 H8 N4 O' _chemical_formula_weight 164.17 _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 direct _atom_sites_solution_secondary difmap _audit_creation_date 2015-08-10 _audit_creation_method ; Olex2 1.2-beta (compiled 2015.01.26 svn.r3150 for OlexSys, GUI svn.r4998) ; _cell_angle_alpha 90 _cell_angle_beta 93.71(3) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 9.381(7) _cell_length_b 12.286(8) _cell_length_c 6.591(5) _cell_measurement_reflns_used 835 _cell_measurement_temperature 150 _cell_measurement_theta_max 23.200 _cell_measurement_theta_min 2.736 _cell_volume 758.1(9) _computing_cell_refinement 'SAINT v8.34A (Bruker, 2013)' _computing_data_collection 'APEX2 v2013.6-2 (Bruker, 2013)' _computing_data_reduction 'SAINT v8.34A (Bruker, 2013)' _computing_molecular_graphics 'Olex2 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2008)' _computing_structure_solution 'XT (Sheldrick, 2008)' _diffrn_ambient_temperature 150 _diffrn_detector 'Bruker APEX CCD' _diffrn_detector_area_resol_mean 8.0 _diffrn_detector_type 'CCD Area Detector' _diffrn_measured_fraction_theta_full 0.928 _diffrn_measured_fraction_theta_max 0.997 _diffrn_measurement_device 'Kappa Four-Circle Diffractometer' _diffrn_measurement_device_type 'Bruker APEX-II CCD' _diffrn_measurement_method '\f and \w scans' _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_unetI/netI 0.1265 _diffrn_reflns_Laue_measured_fraction_full 0.928 _diffrn_reflns_Laue_measured_fraction_max 0.997 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 14 _diffrn_reflns_limit_k_min -14 _diffrn_reflns_limit_l_max 7 _diffrn_reflns_limit_l_min -7 _diffrn_reflns_number 3403 _diffrn_reflns_point_group_measured_fraction_full 0.928 _diffrn_reflns_point_group_measured_fraction_max 0.997 _diffrn_reflns_theta_full 26.000 _diffrn_reflns_theta_max 25.400 _diffrn_reflns_theta_min 2.735 _diffrn_source 'sealed tube' _diffrn_source_type fine-focus _diffrn_standards_number 0 _exptl_absorpt_coefficient_mu 0.104 _exptl_absorpt_correction_T_max 0.0973 _exptl_absorpt_correction_T_min 0.0480 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; TWINABS-2012/1 (Bruker,2012) was used for absorption correction. For component 1: wR2(int) was 0.0519 before and 0.0351 after correction. The Ratio of minimum to maximum transmission not present. The \l/2 correction factor is Not present For component 2: wR2(int) was 0.0535 before and 0.0333 after correction. The Ratio of minimum to maximum transmission is 0.79. The \l/2 correction factor is Not present Final HKLF 4 output contains 6173 reflections, Rint = 0.0651 (2206 with I > 3sig(I), Rint = 0.0398) ; _exptl_crystal_colour colorless _exptl_crystal_colour_primary colorless _exptl_crystal_density_diffrn 1.438 _exptl_crystal_description plate _exptl_crystal_F_000 344 _exptl_crystal_size_max 0.3 _exptl_crystal_size_mid 0.3 _exptl_crystal_size_min 0.1 _refine_diff_density_max 0.244 _refine_diff_density_min -0.404 _refine_diff_density_rms 0.066 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 0.919 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 112 _refine_ls_number_reflns 3403 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 0.919 _refine_ls_R_factor_all 0.1309 _refine_ls_R_factor_gt 0.0561 _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^)+(0.0445P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0972 _refine_ls_wR_factor_ref 0.1159 _reflns_Friedel_coverage 0.000 _reflns_number_gt 1854 _reflns_number_total 3403 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file jo8b00540_si_003.cif _cod_data_source_block dart130 _cod_depositor_comments ; The following automatic conversions were performed: data item '_diffrn_radiation_probe' value 'X-ray' was changed to 'x-ray' in accordance with the /home/data/users/saulius/crontab/automatic-downloads/current/ACS/lib/dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.2 last updated on 2011-04-26. Automatic conversion script Id: cif_fix_values 6909 2019-04-08 15:41:33Z antanas ; _cod_database_code 4035864 _shelxl_version_number 2014-3 _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 0.990 _shelx_estimated_absorpt_t_min 0.970 _olex2_refinement_description ; 1. Twinned data refinement Scales: 0.509(2) 0.491(2) 2. Fixed Uiso At 1.2 times of: All C(H) groups At 1.5 times of: All C(H,H,H) groups 3.a Aromatic/amide H refined with riding coordinates: C006(H006), C00A(H00A) 3.b Idealised Me refined as rotating group: C00B(H00B,H00C,H00D), C00C(H00E,H00F,H00G) ; _shelx_res_file ; TITL PC1C_a.res in P2(1)/c REM Old TITL PC1C in P2(1)/c REM SHELXT solution in P2(1)/c REM R1 0.267, Rweak 0.052, Alpha 0.116, Orientation as input REM Formula found by SHELXT: C10 N O CELL 0.71073 9.381 12.2863 6.5912 90 93.715 90 ZERR 4 0.0065 0.0083 0.0051 0 0.029 0 LATT 1 SYMM -X,0.5+Y,0.5-Z SFAC C H N O UNIT 28 32 16 4 L.S. 10 PLAN 20 SIZE 0.1 0.3 0.3 TEMP -123.15 BOND $H fmap 2 MORE -1 ACTA 52 CONF REM REM REM WGHT 0.044500 BASF 0.49117 FVAR 0.62515 O001 4 0.394441 0.269146 0.746081 11.00000 0.01558 0.01892 = 0.04897 -0.00001 0.00253 -0.00196 N002 3 0.841635 0.185603 0.737603 11.00000 0.02170 0.01687 = 0.02444 -0.00188 0.00170 0.00213 N003 3 0.501008 0.437901 0.747064 11.00000 0.02425 0.01383 = 0.03687 -0.00141 0.00398 -0.00275 N004 3 0.888607 0.290921 0.737192 11.00000 0.01968 0.02274 = 0.02878 -0.00043 0.00233 -0.00297 N005 3 0.759946 0.458371 0.741364 11.00000 0.02278 0.01903 = 0.04494 -0.00029 0.00120 -0.00313 C006 1 0.700705 0.173882 0.740983 11.00000 0.01618 0.01744 = 0.02343 -0.00096 0.00270 -0.00313 AFIX 43 H006 2 0.648750 0.107556 0.742774 11.00000 -1.20000 AFIX 0 C007 1 0.765927 0.347473 0.739876 11.00000 0.02414 0.01719 = 0.01697 -0.00168 0.00125 -0.00020 C008 1 0.512129 0.331439 0.743929 11.00000 0.01987 0.01906 = 0.01809 -0.00108 0.00129 -0.00374 C009 1 0.645505 0.278585 0.741347 11.00000 0.01558 0.01567 = 0.01501 0.00101 0.00022 -0.00163 C00A 1 0.627635 0.494202 0.744564 11.00000 0.03580 0.01261 = 0.04115 -0.00003 -0.00142 -0.00117 AFIX 43 H00A 2 0.618246 0.571188 0.745252 11.00000 -1.20000 AFIX 0 C00B 1 0.948114 0.098589 0.739316 11.00000 0.02021 0.02787 = 0.04998 0.00080 0.00507 0.00547 AFIX 137 H00B 2 1.002459 0.104215 0.617682 11.00000 -1.50000 H00C 2 0.899934 0.027837 0.740433 11.00000 -1.50000 H00D 2 1.013290 0.105413 0.860981 11.00000 -1.50000 AFIX 0 C00C 1 0.258329 0.326056 0.747162 11.00000 0.01376 0.03266 = 0.07329 0.00001 0.00511 0.00223 AFIX 137 H00E 2 0.247796 0.374847 0.629524 11.00000 -1.50000 H00F 2 0.255375 0.368666 0.872509 11.00000 -1.50000 H00G 2 0.180215 0.272953 0.740179 11.00000 -1.50000 AFIX 0 HKLF 5 REM PC1C_a.res in P2(1)/c REM R1 = 0.0561 for 1854 Fo > 4sig(Fo) and 0.1309 for all 3403 data REM 112 parameters refined using 0 restraints END WGHT 0.0445 0.0000 REM Highest difference peak 0.244, deepest hole -0.404, 1-sigma level 0.066 Q1 1 0.9632 0.2970 0.6876 11.00000 0.05 0.24 Q2 1 0.1040 0.3631 0.8890 11.00000 0.05 0.24 Q3 1 0.3490 0.4212 0.9167 11.00000 0.05 0.23 Q4 1 0.9581 0.0507 0.9091 11.00000 0.05 0.22 Q5 1 0.6682 0.0464 0.6663 11.00000 0.05 0.21 Q6 1 0.5892 0.6627 0.5698 11.00000 0.05 0.19 Q7 1 0.5812 0.2989 0.7620 11.00000 0.05 0.19 Q8 1 0.7340 0.0356 0.9248 11.00000 0.05 0.19 Q9 1 0.7336 0.3404 0.5636 11.00000 0.05 0.19 Q10 1 0.6606 0.0792 0.8145 11.00000 0.05 0.19 Q11 1 0.0425 0.2852 0.9071 11.00000 0.05 0.18 Q12 1 0.5323 0.1222 0.8832 11.00000 0.05 0.18 Q13 1 0.5641 0.2618 0.6286 11.00000 0.05 0.18 Q14 1 0.8799 0.3346 0.6133 11.00000 0.05 0.18 Q15 1 0.6188 0.5506 0.8536 11.00000 0.05 0.18 Q16 1 0.5988 0.3282 0.8795 11.00000 0.05 0.17 Q17 1 0.7944 0.4407 0.9195 11.00000 0.05 0.17 Q18 1 1.0089 -0.0458 0.8696 11.00000 0.05 0.17 Q19 1 0.4403 0.2074 0.6123 11.00000 0.05 0.17 Q20 1 0.2244 0.4614 0.6230 11.00000 0.05 0.17 ; _shelx_res_checksum 112 _shelx_hkl_file ; 2 0 0 284.248 4.79505 -2 2 0 0 284.248 4.79505 1 3 0 0 22.2070 2.35949 -2 3 0 0 22.2070 2.35949 1 4 0 0 34.7096 2.41684 -2 4 0 0 34.7096 2.41684 1 5 0 0 28.0311 2.27411 -2 5 0 0 28.0311 2.27411 1 6 0 0 8.28743 1.85037 -2 6 0 0 8.28743 1.85037 1 7 0 0 150.405 4.88557 -2 7 0 0 150.405 4.88557 1 8 0 0 443.533 11.3615 -2 8 0 0 443.533 11.3615 1 9 0 0 117.321 10.2046 -2 9 0 0 117.321 10.2046 1 10 0 0 -0.6744 3.40408 -2 10 0 0 -0.6744 3.40408 1 11 0 0 51.8444 11.0566 -2 11 0 0 51.8444 11.0566 1 0 1 0 0.15540 0.55504 -2 0 -1 0 0.15540 0.55504 1 0 -1 0 0.08829 0.40817 -2 0 1 0 0.08829 0.40817 1 1 1 0 1193.55 8.39132 -2 -1 -1 0 1193.55 8.39132 1 -1 -1 0 1198.64 8.67323 -2 1 1 0 1198.64 8.67323 1 2 1 0 871.716 7.59650 -2 -2 -1 0 871.716 7.59650 1 -2 -1 0 801.109 5.55149 -2 2 1 0 801.109 5.55149 1 3 1 0 19.5597 1.75805 -2 -3 -1 0 19.5597 1.75805 1 -3 -1 0 17.2249 1.54967 -2 3 1 0 17.2249 1.54967 1 4 1 0 161.184 3.97856 -2 -4 -1 0 161.184 3.97856 1 -4 -1 0 144.951 3.33887 -2 4 1 0 144.951 3.33887 1 5 1 0 88.8027 3.53064 -2 -5 -1 0 88.8027 3.53064 1 -5 -1 0 87.5100 3.11312 -2 5 1 0 87.5100 3.11312 1 6 1 0 98.6029 3.70531 -2 -6 -1 0 98.6029 3.70531 1 -6 -1 0 100.778 3.77911 -2 6 1 0 100.778 3.77911 1 7 1 0 115.616 4.49441 -2 -7 -1 0 115.616 4.49441 1 -7 -1 0 122.007 5.21462 -2 7 1 0 122.007 5.21462 1 8 1 0 93.9443 9.18553 -2 -8 -1 0 93.9443 9.18553 1 -8 -1 0 83.9297 8.30815 -2 8 1 0 83.9297 8.30815 1 9 1 0 31.2705 8.46868 -2 -9 -1 0 31.2705 8.46868 1 -9 -1 0 27.2125 4.40141 -2 9 1 0 27.2125 4.40141 1 10 1 0 24.0577 8.99453 -2 -10 -1 0 24.0577 8.99453 1 -10 -1 0 5.67195 3.94513 -2 10 1 0 5.67195 3.94513 1 11 1 0 6.94792 8.74275 -2 -11 -1 0 6.94792 8.74275 1 -11 -1 0 -2.4557 7.64138 -2 11 1 0 -2.4557 7.64138 1 0 2 0 1301.58 10.0065 -2 0 -2 0 1301.58 10.0065 1 0 -2 0 1227.43 9.53851 -2 0 2 0 1227.43 9.53851 1 1 2 0 1.45598 0.62570 -2 -1 -2 0 1.45598 0.62570 1 -1 -2 0 0.99181 0.63966 -2 1 2 0 0.99181 0.63966 1 2 2 0 176.748 2.49338 -2 -2 -2 0 176.748 2.49338 1 -2 -2 0 154.337 2.75585 -2 2 2 0 154.337 2.75585 1 3 2 0 0.88052 1.14940 -2 -3 -2 0 0.88052 1.14940 1 -3 -2 0 -0.0259 1.04193 -2 3 2 0 -0.0259 1.04193 1 4 2 0 641.703 7.41647 -2 -4 -2 0 641.703 7.41647 1 -4 -2 0 593.451 6.89030 -2 4 2 0 593.451 6.89030 1 5 2 0 0.47344 1.38429 -2 -5 -2 0 0.47344 1.38429 1 -5 -2 0 -0.4355 1.22054 -2 5 2 0 -0.4355 1.22054 1 6 2 0 0.49130 1.41877 -2 -6 -2 0 0.49130 1.41877 1 -6 -2 0 -0.5842 1.43964 -2 6 2 0 -0.5842 1.43964 1 7 2 0 83.9472 4.42586 -2 -7 -2 0 83.9472 4.42586 1 -7 -2 0 77.3420 5.15330 -2 7 2 0 77.3420 5.15330 1 8 2 0 2.77323 4.37083 -2 -8 -2 0 2.77323 4.37083 1 9 2 0 0.38740 7.30981 -2 -9 -2 0 0.38740 7.30981 1 -9 -2 0 0.84939 3.54989 -2 9 2 0 0.84939 3.54989 1 10 2 0 19.7798 8.99861 -2 -10 -2 0 19.7798 8.99861 1 -10 -2 0 3.00507 3.47937 -2 10 2 0 3.00507 3.47937 1 11 2 0 20.5373 10.1859 -2 -11 -2 0 20.5373 10.1859 1 -11 -2 0 -2.9087 5.08659 -2 11 2 0 -2.9087 5.08659 1 0 3 0 0.62227 1.99987 -2 0 -3 0 0.62227 1.99987 1 0 -3 0 1.05013 1.57331 -2 0 3 0 1.05013 1.57331 1 1 3 0 63.8473 1.75588 -2 -1 -3 0 63.8473 1.75588 1 -1 -3 0 68.7003 2.45686 -2 1 3 0 68.7003 2.45686 1 2 3 0 79.8928 1.85197 -2 -2 -3 0 79.8928 1.85197 1 -2 -3 0 89.1200 2.04207 -2 2 3 0 89.1200 2.04207 1 3 3 0 0.67317 0.86465 -2 -3 -3 0 0.67317 0.86465 1 -3 -3 0 0.84902 0.99217 -2 3 3 0 0.84902 0.99217 1 4 3 0 23.0730 1.57540 -2 -4 -3 0 23.0730 1.57540 1 -4 -3 0 21.4765 2.00700 -2 4 3 0 21.4765 2.00700 1 5 3 0 363.259 4.61310 -2 -5 -3 0 363.259 4.61310 1 -5 -3 0 360.193 8.28708 -2 5 3 0 360.193 8.28708 1 6 3 0 179.822 3.94312 -2 -6 -3 0 179.822 3.94312 1 -6 -3 0 186.138 6.91530 -2 6 3 0 186.138 6.91530 1 7 3 0 21.8481 2.71435 -2 -7 -3 0 21.8481 2.71435 1 8 3 0 35.8578 6.69483 -2 -8 -3 0 35.8578 6.69483 1 -8 -3 0 43.6766 7.20508 -2 8 3 0 43.6766 7.20508 1 9 3 0 -4.7956 7.24882 -2 -9 -3 0 -4.7956 7.24882 1 -9 -3 0 -4.4866 3.74166 -2 9 3 0 -4.4866 3.74166 1 10 3 0 6.74423 8.10750 -2 -10 -3 0 6.74423 8.10750 1 -10 -3 0 1.00086 3.47525 -2 10 3 0 1.00086 3.47525 1 11 3 0 0.96630 8.13482 -2 -11 -3 0 0.96630 8.13482 1 -11 -3 0 2.32557 4.01638 -2 11 3 0 2.32557 4.01638 1 0 4 0 156.023 6.23676 -2 0 -4 0 156.023 6.23676 1 0 -4 0 159.502 4.37387 -2 0 4 0 159.502 4.37387 1 1 4 0 353.736 4.57752 -2 -1 -4 0 353.736 4.57752 1 -1 -4 0 339.651 4.71140 -2 1 4 0 339.651 4.71140 1 2 4 0 1.18680 0.87017 -2 -2 -4 0 1.18680 0.87017 1 -2 -4 0 1.52452 1.02215 -2 2 4 0 1.52452 1.02215 1 3 4 0 57.5845 1.90058 -2 -3 -4 0 57.5845 1.90058 1 -3 -4 0 58.0430 1.98029 -2 3 4 0 58.0430 1.98029 1 4 4 0 986.897 7.93338 -2 -4 -4 0 986.897 7.93338 1 -4 -4 0 1083.01 12.4393 -2 4 4 0 1083.01 12.4393 1 5 4 0 119.196 2.73088 -2 -5 -4 0 119.196 2.73088 1 -5 -4 0 124.391 4.90383 -2 5 4 0 124.391 4.90383 1 6 4 0 8.58555 1.42068 -2 -6 -4 0 8.58555 1.42068 1 -6 -4 0 4.49619 2.00285 -2 6 4 0 4.49619 2.00285 1 7 4 0 3.98116 1.81335 -2 -7 -4 0 3.98116 1.81335 1 -7 -4 0 7.27637 2.18357 -2 7 4 0 7.27637 2.18357 1 8 4 0 67.2391 9.12190 -2 -8 -4 0 67.2391 9.12190 1 -8 -4 0 52.2200 7.75934 -2 8 4 0 52.2200 7.75934 1 9 4 0 -1.5902 7.62556 -2 -9 -4 0 -1.5902 7.62556 1 -9 -4 0 -3.3147 4.27400 -2 9 4 0 -3.3147 4.27400 1 10 4 0 5.35597 8.47435 -2 -10 -4 0 5.35597 8.47435 1 -10 -4 0 11.4145 5.91589 -2 10 4 0 11.4145 5.91589 1 0 5 0 0.67121 1.75153 -2 0 -5 0 0.67121 1.75153 1 0 -5 0 2.18214 1.89039 -2 0 5 0 2.18214 1.89039 1 1 5 0 1.21354 1.58421 -2 -1 -5 0 1.21354 1.58421 1 -1 -5 0 -0.1515 1.16206 -2 1 5 0 -0.1515 1.16206 1 2 5 0 50.4272 1.87888 -2 -2 -5 0 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-6 12.7053 5.32300 1 -3 -3 -6 18.7169 8.65869 -2 -4 3 6 18.7169 8.65869 1 2 3 6 -4.9592 8.55910 -2 3 -3 -6 -4.9592 8.55910 1 -2 -3 -6 9.75671 7.71559 -2 -3 3 6 9.75671 7.71559 1 1 3 6 1.69112 9.07347 -2 2 -3 -6 1.69112 9.07347 1 -1 -3 -6 0.58924 7.00856 -2 -2 3 6 0.58924 7.00856 1 0 3 6 16.6002 9.55531 -2 1 -3 -6 16.6002 9.55531 1 0 -3 -6 -2.9359 6.58260 -2 -1 3 6 -2.9359 6.58260 1 -1 3 6 7.84978 9.10102 -2 0 -3 -6 7.84978 9.10102 1 1 -3 -6 -5.9653 5.87149 -2 0 3 6 -5.9653 5.87149 1 -2 3 6 7.92092 9.51484 -2 -1 -3 -6 7.92092 9.51484 1 2 -3 -6 4.52138 6.46758 -2 1 3 6 4.52138 6.46758 1 -3 3 6 -13.697 8.85485 -2 -2 -3 -6 -13.697 8.85485 1 3 -3 -6 4.97884 4.68962 -2 2 3 6 4.97884 4.68962 1 -4 3 6 26.0651 10.4678 -2 -3 -3 -6 26.0651 10.4678 1 4 -3 -6 12.5625 4.92739 -2 3 3 6 12.5625 4.92739 1 -5 3 6 21.0835 10.4518 -2 -4 -3 -6 21.0835 10.4518 1 5 -3 -6 15.2242 9.37512 -2 4 3 6 15.2242 9.37512 1 -6 3 6 43.3281 10.5414 -2 -5 -3 -6 43.3281 10.5414 1 6 -3 -6 50.9844 10.8739 -2 5 3 6 50.9844 10.8739 1 7 -3 -6 3.46628 7.66755 -2 6 3 6 3.46628 7.66755 1 6 4 6 1.96770 6.43625 -2 7 -4 -6 1.96770 6.43625 1 -6 -4 -6 23.0842 17.5584 -2 -7 4 6 23.0842 17.5584 1 5 4 6 12.2205 5.78409 -2 6 -4 -6 12.2205 5.78409 1 -5 -4 -6 -3.3087 13.4712 -2 -6 4 6 -3.3087 13.4712 1 4 4 6 35.5926 6.39558 -2 5 -4 -6 35.5926 6.39558 1 -4 -4 -6 47.3727 9.35951 -2 -5 4 6 47.3727 9.35951 1 3 4 6 31.7520 6.07324 -2 4 -4 -6 31.7520 6.07324 1 -3 -4 -6 43.1471 9.24892 -2 -4 4 6 43.1471 9.24892 1 2 4 6 5.16514 8.89680 -2 3 -4 -6 5.16514 8.89680 1 -2 -4 -6 19.5848 8.21232 -2 -3 4 6 19.5848 8.21232 1 1 4 6 -5.5651 8.95833 -2 2 -4 -6 -5.5651 8.95833 1 -1 -4 -6 0.13958 6.80826 -2 -2 4 6 0.13958 6.80826 1 0 4 6 8.88181 9.44802 -2 1 -4 -6 8.88181 9.44802 1 0 -4 -6 1.84487 6.75466 -2 -1 4 6 1.84487 6.75466 1 -1 4 6 17.3125 9.49181 -2 0 -4 -6 17.3125 9.49181 1 1 -4 -6 8.54386 6.60899 -2 0 4 6 8.54386 6.60899 1 -2 4 6 1.41386 9.90232 -2 -1 -4 -6 1.41386 9.90232 1 2 -4 -6 3.99315 4.94933 -2 1 4 6 3.99315 4.94933 1 -3 4 6 17.4823 10.1339 -2 -2 -4 -6 17.4823 10.1339 1 3 -4 -6 15.7384 4.81983 -2 2 4 6 15.7384 4.81983 1 -4 4 6 57.3215 12.0921 -2 -3 -4 -6 57.3215 12.0921 1 4 -4 -6 49.7588 7.46722 -2 3 4 6 49.7588 7.46722 1 -5 4 6 43.7466 11.8046 -2 -4 -4 -6 43.7466 11.8046 1 5 -4 -6 45.4235 9.92693 -2 4 4 6 45.4235 9.92693 1 -6 4 6 9.05764 10.4201 -2 -5 -4 -6 9.05764 10.4201 1 6 -4 -6 28.9500 9.83884 -2 5 4 6 28.9500 9.83884 1 7 -4 -6 -5.3990 9.52209 -2 6 4 6 -5.3990 9.52209 1 5 5 6 10.1421 6.96687 -2 6 -5 -6 10.1421 6.96687 1 -5 -5 -6 0.53821 15.6503 -2 -6 5 6 0.53821 15.6503 1 4 5 6 -4.6318 7.29497 -2 5 -5 -6 -4.6318 7.29497 1 -4 -5 -6 6.55001 14.2769 -2 -5 5 6 6.55001 14.2769 1 3 5 6 19.2504 9.95862 -2 4 -5 -6 19.2504 9.95862 1 -3 -5 -6 -0.6691 8.04885 -2 -4 5 6 -0.6691 8.04885 1 2 5 6 11.1332 9.78194 -2 3 -5 -6 11.1332 9.78194 1 -2 -5 -6 1.59471 7.51931 -2 -3 5 6 1.59471 7.51931 1 1 5 6 13.4030 10.0084 -2 2 -5 -6 13.4030 10.0084 1 -1 -5 -6 6.08187 7.68088 -2 -2 5 6 6.08187 7.68088 1 0 5 6 -11.547 8.99848 -2 1 -5 -6 -11.547 8.99848 1 0 -5 -6 6.68440 6.88964 -2 -1 5 6 6.68440 6.88964 1 -1 5 6 -9.5558 9.62451 -2 0 -5 -6 -9.5558 9.62451 1 1 -5 -6 0.73956 5.12988 -2 0 5 6 0.73956 5.12988 1 -2 5 6 -13.556 9.60762 -2 -1 -5 -6 -13.556 9.60762 1 2 -5 -6 0.68087 4.84889 -2 1 5 6 0.68087 4.84889 1 -3 5 6 11.8245 10.5357 -2 -2 -5 -6 11.8245 10.5357 1 3 -5 -6 -4.3911 6.72777 -2 2 5 6 -4.3911 6.72777 1 -4 5 6 -9.9988 10.4847 -2 -3 -5 -6 -9.9988 10.4847 1 4 -5 -6 -2.0352 8.56738 -2 3 5 6 -2.0352 8.56738 1 -5 5 6 -15.533 10.8011 -2 -4 -5 -6 -15.533 10.8011 1 5 -5 -6 6.81648 9.02476 -2 4 5 6 6.81648 9.02476 1 6 -5 -6 -1.8132 10.0923 -2 5 5 6 -1.8132 10.0923 1 5 6 6 5.41124 7.98663 -2 6 -6 -6 5.41124 7.98663 1 -5 -6 -6 -14.961 15.8373 -2 -6 6 6 -14.961 15.8373 1 4 6 6 2.90518 9.80546 -2 5 -6 -6 2.90518 9.80546 1 -4 -6 -6 24.2981 15.2751 -2 -5 6 6 24.2981 15.2751 1 3 6 6 17.3084 9.75492 -2 4 -6 -6 17.3084 9.75492 1 -3 -6 -6 0.54365 15.4925 -2 -4 6 6 0.54365 15.4925 1 2 6 6 23.2538 10.3044 -2 3 -6 -6 23.2538 10.3044 1 -2 -6 -6 16.0167 14.0566 -2 -3 6 6 16.0167 14.0566 1 1 6 6 34.1588 10.6840 -2 2 -6 -6 34.1588 10.6840 1 -1 -6 -6 24.3536 7.36892 -2 -2 6 6 24.3536 7.36892 1 0 6 6 26.5052 9.62305 -2 1 -6 -6 26.5052 9.62305 1 0 -6 -6 15.2136 5.71189 -2 -1 6 6 15.2136 5.71189 1 -1 6 6 18.9888 10.4684 -2 0 -6 -6 18.9888 10.4684 1 1 -6 -6 12.4497 5.66121 -2 0 6 6 12.4497 5.66121 1 -2 6 6 41.9406 10.6911 -2 -1 -6 -6 41.9406 10.6911 1 2 -6 -6 23.6311 7.64971 -2 1 6 6 23.6311 7.64971 1 -3 6 6 24.9417 11.5554 -2 -2 -6 -6 24.9417 11.5554 1 3 -6 -6 25.6894 7.19894 -2 2 6 6 25.6894 7.19894 1 -4 6 6 5.26435 10.2067 -2 -3 -6 -6 5.26435 10.2067 1 4 -6 -6 1.72182 9.16348 -2 3 6 6 1.72182 9.16348 1 -5 6 6 9.77693 11.8250 -2 -4 -6 -6 9.77693 11.8250 1 5 -6 -6 24.6807 10.5143 -2 4 6 6 24.6807 10.5143 1 6 -6 -6 0.56566 10.8679 -2 5 6 6 0.56566 10.8679 1 4 7 6 -6.8643 9.57904 -2 5 -7 -6 -6.8643 9.57904 1 -4 -7 -6 18.8116 15.7757 -2 -5 7 6 18.8116 15.7757 1 3 7 6 7.23029 9.55449 -2 4 -7 -6 7.23029 9.55449 1 -3 -7 -6 31.6564 16.0789 -2 -4 7 6 31.6564 16.0789 1 2 7 6 5.64841 10.1105 -2 3 -7 -6 5.64841 10.1105 1 -2 -7 -6 5.30368 13.7699 -2 -3 7 6 5.30368 13.7699 1 1 7 6 17.4205 10.3725 -2 2 -7 -6 17.4205 10.3725 1 -1 -7 -6 14.9467 13.8857 -2 -2 7 6 14.9467 13.8857 1 0 7 6 27.8937 10.7909 -2 1 -7 -6 27.8937 10.7909 1 0 -7 -6 25.4088 8.97301 -2 -1 7 6 25.4088 8.97301 1 -1 7 6 6.09045 10.1910 -2 0 -7 -6 6.09045 10.1910 1 1 -7 -6 24.2145 8.61000 -2 0 7 6 24.2145 8.61000 1 -2 7 6 33.4624 11.9700 -2 -1 -7 -6 33.4624 11.9700 1 2 -7 -6 18.3711 7.90095 -2 1 7 6 18.3711 7.90095 1 -3 7 6 0.13764 11.5619 -2 -2 -7 -6 0.13764 11.5619 1 3 -7 -6 -5.9926 9.40438 -2 2 7 6 -5.9926 9.40438 1 -4 7 6 7.71230 11.6730 -2 -3 -7 -6 7.71230 11.6730 1 4 -7 -6 7.82221 10.3598 -2 3 7 6 7.82221 10.3598 1 -5 7 6 4.31887 11.0283 -2 -4 -7 -6 4.31887 11.0283 1 5 -7 -6 0.75805 9.97856 -2 4 7 6 0.75805 9.97856 1 3 8 6 30.2389 10.7549 -2 4 -8 -6 30.2389 10.7549 1 -3 -8 -6 43.7706 15.7924 -2 -4 8 6 43.7706 15.7924 1 2 8 6 25.0928 10.5243 -2 3 -8 -6 25.0928 10.5243 1 -2 -8 -6 33.3107 16.9619 -2 -3 8 6 33.3107 16.9619 1 1 8 6 3.34398 10.0937 -2 2 -8 -6 3.34398 10.0937 1 -1 -8 -6 6.54983 8.95292 -2 -2 8 6 6.54983 8.95292 1 0 8 6 7.28827 10.1794 -2 1 -8 -6 7.28827 10.1794 1 0 -8 -6 14.7266 9.11952 -2 -1 8 6 14.7266 9.11952 1 -1 8 6 43.7644 12.1719 -2 0 -8 -6 43.7644 12.1719 1 1 -8 -6 22.8214 8.69143 -2 0 8 6 22.8214 8.69143 1 -2 8 6 27.0087 11.6246 -2 -1 -8 -6 27.0087 11.6246 1 2 -8 -6 1.56924 7.48840 -2 1 8 6 1.56924 7.48840 1 -3 8 6 17.1077 11.5682 -2 -2 -8 -6 17.1077 11.5682 1 3 -8 -6 37.1139 11.1096 -2 2 8 6 37.1139 11.1096 1 -4 8 6 39.7707 12.0116 -2 -3 -8 -6 39.7707 12.0116 1 4 -8 -6 37.2780 12.9030 -2 3 8 6 37.2780 12.9030 1 2 9 6 23.4345 10.6065 -2 3 -9 -6 23.4345 10.6065 1 -2 -9 -6 41.0139 17.9061 -2 -3 9 6 41.0139 17.9061 1 1 9 6 18.7998 10.5752 -2 2 -9 -6 18.7998 10.5752 1 -1 -9 -6 -14.952 8.64769 -2 -2 9 6 -14.952 8.64769 1 0 9 6 -5.3551 10.2630 -2 1 -9 -6 -5.3551 10.2630 1 0 -9 -6 -0.3984 8.95586 -2 -1 9 6 -0.3984 8.95586 1 -1 9 6 12.2724 10.6316 -2 0 -9 -6 12.2724 10.6316 1 1 -9 -6 -5.5447 7.88837 -2 0 9 6 -5.5447 7.88837 1 -2 9 6 -5.1130 10.3363 -2 -1 -9 -6 -5.1130 10.3363 1 2 -9 -6 10.2341 10.8617 -2 1 9 6 10.2341 10.8617 1 -3 9 6 21.4343 12.2135 -2 -2 -9 -6 21.4343 12.2135 1 3 -9 -6 21.8994 12.7719 -2 2 9 6 21.8994 12.7719 1 -6 0 7 -3.7174 4.80913 1 -6 0 7 2.81718 5.17734 2 4 0 7 -0.4716 10.6337 -2 -5 0 7 -0.4716 10.6337 1 3 0 7 -14.108 9.07750 -2 -4 0 7 -14.108 9.07750 1 2 0 7 7.63508 10.0605 -2 -3 0 7 7.63508 10.0605 1 1 0 7 -7.4704 9.17945 -2 -2 0 7 -7.4704 9.17945 1 0 0 7 3.76159 8.82982 -2 -1 0 7 3.76159 8.82982 1 -1 0 7 2.65333 9.12016 -2 0 0 7 2.65333 9.12016 1 -2 0 7 1.37034 9.20695 -2 1 0 7 1.37034 9.20695 1 -3 0 7 -2.5970 10.9456 -2 2 0 7 -2.5970 10.9456 1 -4 0 7 11.2835 10.8610 -2 3 0 7 11.2835 10.8610 1 -5 0 7 -14.094 10.6292 -2 4 0 7 -14.094 10.6292 1 4 1 7 2.70541 10.1681 -2 5 -1 -7 2.70541 10.1681 1 -4 -1 -7 -2.7341 9.79754 -2 -5 1 7 -2.7341 9.79754 1 3 1 7 5.15946 10.4672 -2 4 -1 -7 5.15946 10.4672 1 -3 -1 -7 5.33619 10.3112 -2 -4 1 7 5.33619 10.3112 1 2 1 7 -3.6641 9.08358 -2 3 -1 -7 -3.6641 9.08358 1 -2 -1 -7 12.8792 9.34022 -2 -3 1 7 12.8792 9.34022 1 1 1 7 13.5875 9.27990 -2 2 -1 -7 13.5875 9.27990 1 -1 -1 -7 -6.9440 9.35792 -2 -2 1 7 -6.9440 9.35792 1 0 1 7 10.2761 8.86717 -2 1 -1 -7 10.2761 8.86717 1 0 -1 -7 14.6496 9.52012 -2 -1 1 7 14.6496 9.52012 1 -1 1 7 18.0625 11.9739 -2 0 -1 -7 18.0625 11.9739 1 1 -1 -7 5.73391 10.8520 -2 0 1 7 5.73391 10.8520 1 -2 1 7 4.15089 12.0123 -2 -1 -1 -7 4.15089 12.0123 1 2 -1 -7 -2.6532 8.35587 -2 1 1 7 -2.6532 8.35587 1 -3 1 7 1.34724 11.3020 -2 -2 -1 -7 1.34724 11.3020 1 3 -1 -7 2.19925 8.77977 -2 2 1 7 2.19925 8.77977 1 -4 1 7 -2.8139 10.7025 -2 -3 -1 -7 -2.8139 10.7025 1 4 -1 -7 11.0274 9.03224 -2 3 1 7 11.0274 9.03224 1 -5 1 7 -0.2002 11.2169 -2 -4 -1 -7 -0.2002 11.2169 1 5 -1 -7 -10.257 10.2571 -2 4 1 7 -10.257 10.2571 1 4 2 7 5.53969 9.75500 -2 5 -2 -7 5.53969 9.75500 1 -4 -2 -7 22.4457 11.2546 -2 -5 2 7 22.4457 11.2546 1 3 2 7 1.69326 9.72748 -2 4 -2 -7 1.69326 9.72748 1 -3 -2 -7 2.16979 9.75883 -2 -4 2 7 2.16979 9.75883 1 2 2 7 20.8140 10.1373 -2 3 -2 -7 20.8140 10.1373 1 -2 -2 -7 7.09769 10.2060 -2 -3 2 7 7.09769 10.2060 1 1 2 7 8.61541 9.68647 -2 2 -2 -7 8.61541 9.68647 1 -1 -2 -7 4.21400 9.57131 -2 -2 2 7 4.21400 9.57131 1 0 2 7 5.11442 12.2018 -2 1 -2 -7 5.11442 12.2018 1 0 -2 -7 27.2344 9.92335 -2 -1 2 7 27.2344 9.92335 1 -1 2 7 22.2551 12.0364 -2 0 -2 -7 22.2551 12.0364 1 1 -2 -7 37.3329 9.86453 -2 0 2 7 37.3329 9.86453 1 -2 2 7 19.4573 11.5093 -2 -1 -2 -7 19.4573 11.5093 1 2 -2 -7 11.9144 8.69555 -2 1 2 7 11.9144 8.69555 1 -3 2 7 9.04414 11.4421 -2 -2 -2 -7 9.04414 11.4421 1 3 -2 -7 20.3484 8.49786 -2 2 2 7 20.3484 8.49786 1 -4 2 7 6.73936 11.7554 -2 -3 -2 -7 6.73936 11.7554 1 4 -2 -7 9.00944 8.43198 -2 3 2 7 9.00944 8.43198 1 -5 2 7 -0.6217 12.1592 -2 -4 -2 -7 -0.6217 12.1592 1 4 3 7 7.74555 10.0432 -2 5 -3 -7 7.74555 10.0432 1 -4 -3 -7 15.3733 11.3632 -2 -5 3 7 15.3733 11.3632 1 3 3 7 7.28187 16.1501 -2 4 -3 -7 7.28187 16.1501 1 -3 -3 -7 13.7843 10.5388 -2 -4 3 7 13.7843 10.5388 1 2 3 7 9.97283 9.71389 -2 3 -3 -7 9.97283 9.71389 1 -2 -3 -7 9.68214 10.1432 -2 -3 3 7 9.68214 10.1432 1 1 3 7 -8.0473 11.9853 -2 2 -3 -7 -8.0473 11.9853 1 -1 -3 -7 18.5975 10.0579 -2 -2 3 7 18.5975 10.0579 1 0 3 7 -18.375 12.3743 -2 1 -3 -7 -18.375 12.3743 1 0 -3 -7 9.54822 9.37954 -2 -1 3 7 9.54822 9.37954 1 -1 3 7 1.11470 12.1197 -2 0 -3 -7 1.11470 12.1197 1 1 -3 -7 7.08057 8.98553 -2 0 3 7 7.08057 8.98553 1 -2 3 7 -9.2235 10.6263 -2 -1 -3 -7 -9.2235 10.6263 1 2 -3 -7 15.8272 10.9863 -2 1 3 7 15.8272 10.9863 1 -3 3 7 -6.2343 11.1009 -2 -2 -3 -7 -6.2343 11.1009 1 3 -3 -7 0.76199 7.94465 -2 2 3 7 0.76199 7.94465 1 -4 3 7 -2.1347 10.9989 -2 -3 -3 -7 -2.1347 10.9989 1 -5 3 7 0.28938 11.7744 -2 -4 -3 -7 0.28938 11.7744 1 5 -4 -7 3.19809 5.08602 1 5 -4 -7 -1.7928 5.08201 2 -5 4 7 1.78900 5.58781 2 -5 4 7 2.48280 4.81900 1 3 4 7 -7.9412 17.4105 -2 4 -4 -7 -7.9412 17.4105 1 4 -4 -7 12.4240 6.40669 1 -3 -4 -7 -6.8114 10.5026 -2 -4 4 7 -6.8114 10.5026 1 2 4 7 3.13350 12.1104 -2 3 -4 -7 3.13350 12.1104 1 -2 -4 -7 8.14265 10.6297 -2 -3 4 7 8.14265 10.6297 1 1 4 7 10.4468 11.8330 -2 2 -4 -7 10.4468 11.8330 1 -1 -4 -7 -2.2452 9.34293 -2 -2 4 7 -2.2452 9.34293 1 0 4 7 12.3838 11.6669 -2 1 -4 -7 12.3838 11.6669 1 0 -4 -7 7.34605 9.01552 -2 -1 4 7 7.34605 9.01552 1 -1 4 7 6.09907 11.2218 -2 0 -4 -7 6.09907 11.2218 1 1 -4 -7 0.17978 8.53877 -2 0 4 7 0.17978 8.53877 1 -2 4 7 7.87919 12.2595 -2 -1 -4 -7 7.87919 12.2595 1 2 -4 -7 5.61457 8.49229 -2 1 4 7 5.61457 8.49229 1 -3 4 7 18.2644 12.0631 -2 -2 -4 -7 18.2644 12.0631 1 3 -4 -7 5.84319 16.5803 -2 2 4 7 5.84319 16.5803 1 -4 4 7 12.0236 12.5489 -2 -3 -4 -7 12.0236 12.5489 1 4 -4 -7 7.15962 12.0057 -2 3 4 7 7.15962 12.0057 1 3 4 7 9.18217 6.46649 2 4 -5 -7 -1.0882 4.92118 1 -3 -5 -7 15.0129 10.4119 -2 -4 5 7 15.0129 10.4119 1 2 5 7 -10.268 11.6299 -2 3 -5 -7 -10.268 11.6299 1 -2 -5 -7 -1.9422 10.1276 -2 -3 5 7 -1.9422 10.1276 1 1 5 7 0.82291 12.9078 -2 2 -5 -7 0.82291 12.9078 1 -1 -5 -7 8.79473 10.2542 -2 -2 5 7 8.79473 10.2542 1 0 5 7 -8.1333 11.5318 -2 1 -5 -7 -8.1333 11.5318 1 0 -5 -7 8.05759 9.82176 -2 -1 5 7 8.05759 9.82176 1 -1 5 7 21.0411 11.5739 -2 0 -5 -7 21.0411 11.5739 1 1 -5 -7 -18.174 15.4129 -2 0 5 7 -18.174 15.4129 1 -2 5 7 4.85229 12.4707 -2 -1 -5 -7 4.85229 12.4707 1 2 -5 -7 1.19722 14.6097 -2 1 5 7 1.19722 14.6097 1 -3 5 7 -2.8624 11.6549 -2 -2 -5 -7 -2.8624 11.6549 1 3 -5 -7 31.1778 12.9681 -2 2 5 7 31.1778 12.9681 1 -4 5 7 43.8806 13.9074 -2 -3 -5 -7 43.8806 13.9074 1 3 5 7 9.40222 6.75987 2 4 -5 -7 21.6715 12.1526 -2 3 5 7 21.6715 12.1526 1 2 6 7 20.6586 12.5755 -2 3 -6 -7 20.6586 12.5755 1 -2 -6 -7 -8.9317 18.2130 -2 -3 6 7 -8.9317 18.2130 1 1 6 7 13.2129 13.0885 -2 2 -6 -7 13.2129 13.0885 1 -1 -6 -7 13.1065 10.1444 -2 -2 6 7 13.1065 10.1444 1 0 6 7 38.3354 13.8180 -2 1 -6 -7 38.3354 13.8180 1 0 -6 -7 6.92008 15.4364 -2 -1 6 7 6.92008 15.4364 1 -1 6 7 26.0870 13.2169 -2 0 -6 -7 26.0870 13.2169 1 1 -6 -7 13.1726 14.0394 -2 0 6 7 13.1726 14.0394 1 -2 6 7 16.0112 13.8062 -2 -1 -6 -7 16.0112 13.8062 1 2 -6 -7 6.04062 9.72704 -2 1 6 7 6.04062 9.72704 1 3 -6 -7 8.82966 12.4057 -2 2 6 7 8.82966 12.4057 1 1 -7 -7 1.29505 6.05656 1 1 -7 -7 0.47485 9.43645 2 -1 7 7 -11.062 8.98961 1 0 0 0 0.00 0.00 0 ; _shelx_hkl_checksum 15249 _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 O001 O 0.3944(2) 0.26915(18) 0.7461(4) 0.0278(8) Uani 1 1 d . N002 N 0.8416(3) 0.1856(2) 0.7376(5) 0.0210(7) Uani 1 1 d . N003 N 0.5010(3) 0.4379(2) 0.7471(4) 0.0249(8) Uani 1 1 d . N004 N 0.8886(3) 0.2909(2) 0.7372(5) 0.0237(8) Uani 1 1 d . N005 N 0.7599(3) 0.4584(2) 0.7414(5) 0.0290(8) Uani 1 1 d . C006 C 0.7007(3) 0.1739(3) 0.7410(5) 0.0190(9) Uani 1 1 d . H006 H 0.6487 0.1076 0.7428 0.023 Uiso 1 1 calc R C007 C 0.7659(4) 0.3475(3) 0.7399(5) 0.0194(9) Uani 1 1 d . C008 C 0.5121(4) 0.3314(3) 0.7439(5) 0.0190(9) Uani 1 1 d . C009 C 0.6455(3) 0.2786(3) 0.7413(5) 0.0155(8) Uani 1 1 d . C00A C 0.6276(4) 0.4942(3) 0.7446(6) 0.0300(10) Uani 1 1 d . H00A H 0.6182 0.5712 0.7453 0.036 Uiso 1 1 calc R C00B C 0.9481(3) 0.0986(3) 0.7393(6) 0.0326(11) Uani 1 1 d . H00B H 1.0025 0.1042 0.6177 0.049 Uiso 1 1 calc GR H00C H 0.8999 0.0278 0.7404 0.049 Uiso 1 1 calc GR H00D H 1.0133 0.1054 0.8610 0.049 Uiso 1 1 calc GR C00C C 0.2583(3) 0.3261(3) 0.7472(7) 0.0398(12) Uani 1 1 d . H00E H 0.2478 0.3748 0.6295 0.060 Uiso 1 1 calc GR H00F H 0.2554 0.3687 0.8725 0.060 Uiso 1 1 calc GR H00G H 0.1802 0.2730 0.7402 0.060 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 O001 0.0156(14) 0.0189(16) 0.049(2) 0.0000(14) 0.0025(15) -0.0020(11) N002 0.0217(18) 0.0169(17) 0.024(2) -0.0019(17) 0.0017(16) 0.0021(14) N003 0.0243(18) 0.0138(17) 0.037(2) -0.0014(16) 0.0040(16) -0.0027(15) N004 0.0197(18) 0.0227(19) 0.029(2) -0.0004(18) 0.0023(17) -0.0030(14) N005 0.023(2) 0.0190(18) 0.045(2) -0.0003(18) 0.0012(19) -0.0031(14) C006 0.016(2) 0.017(2) 0.023(2) -0.0010(19) 0.0027(18) -0.0031(16) C007 0.024(2) 0.017(2) 0.017(2) -0.002(2) 0.001(2) -0.0002(18) C008 0.020(2) 0.019(2) 0.018(2) -0.0011(19) 0.0013(17) -0.0037(17) C009 0.0156(19) 0.016(2) 0.015(2) 0.0010(19) 0.0002(16) -0.0016(17) C00A 0.036(3) 0.013(2) 0.041(3) 0.000(2) -0.001(2) -0.0012(19) C00B 0.020(2) 0.028(3) 0.050(3) 0.001(2) 0.005(2) 0.0055(17) C00C 0.014(2) 0.033(2) 0.073(3) 0.000(3) 0.005(2) 0.0022(18) 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' O O 0.0106 0.0060 '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 C008 O001 C00C 116.6(3) N004 N002 C00B 118.2(3) C006 N002 N004 115.0(3) C006 N002 C00B 126.8(3) C008 N003 C00A 115.6(3) C007 N004 N002 102.3(3) C00A N005 C007 111.9(3) N002 C006 H006 127.1 N002 C006 C009 105.7(3) C009 C006 H006 127.1 N004 C007 N005 123.5(3) N004 C007 C009 112.1(3) N005 C007 C009 124.4(3) O001 C008 C009 117.9(3) N003 C008 O001 120.1(3) N003 C008 C009 122.0(3) C006 C009 C007 104.9(3) C006 C009 C008 139.3(3) C008 C009 C007 115.8(3) N003 C00A H00A 114.8 N005 C00A N003 130.3(3) N005 C00A H00A 114.8 N002 C00B H00B 109.5 N002 C00B H00C 109.5 N002 C00B H00D 109.5 H00B C00B H00C 109.5 H00B C00B H00D 109.5 H00C C00B H00D 109.5 O001 C00C H00E 109.5 O001 C00C H00F 109.5 O001 C00C H00G 109.5 H00E C00C H00F 109.5 H00E C00C H00G 109.5 H00F C00C H00G 109.5 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance O001 C008 1.344(3) O001 C00C 1.456(4) N002 N004 1.367(3) N002 C006 1.331(4) N002 C00B 1.463(4) N003 C008 1.312(4) N003 C00A 1.376(4) N004 C007 1.345(4) N005 C007 1.364(4) N005 C00A 1.318(4) C006 H006 0.9500 C006 C009 1.387(4) C007 C009 1.412(4) C008 C009 1.411(4) C00A H00A 0.9500 C00B H00B 0.9800 C00B H00C 0.9800 C00B H00D 0.9800 C00C H00E 0.9800 C00C H00F 0.9800 C00C H00G 0.9800 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 O001 C008 C009 C006 -0.3(7) O001 C008 C009 C007 -179.8(3) N002 N004 C007 N005 179.7(3) N002 N004 C007 C009 -0.2(4) N002 C006 C009 C007 -0.5(4) N002 C006 C009 C008 180.0(5) N003 C008 C009 C006 178.7(4) N003 C008 C009 C007 -0.7(6) N004 N002 C006 C009 0.5(4) N004 C007 C009 C006 0.4(4) N004 C007 C009 C008 -179.9(3) N005 C007 C009 C006 -179.4(4) N005 C007 C009 C008 0.2(6) C006 N002 N004 C007 -0.2(4) C007 N005 C00A N003 0.2(7) C008 N003 C00A N005 -0.7(7) C00A N003 C008 O001 180.0(3) C00A N003 C008 C009 0.9(6) C00A N005 C007 N004 -179.8(3) C00A N005 C007 C009 0.1(6) C00B N002 N004 C007 -178.8(3) C00B N002 C006 C009 178.9(3) C00C O001 C008 N003 1.4(5) C00C O001 C008 C009 -179.5(3) loop_ _twin_individual_id _twin_individual_mass_fraction_refined 1 0.509(2) 2 0.491(2)