#------------------------------------------------------------------------------ #$Date: 2021-12-07 05:53:38 +0200 (Tue, 07 Dec 2021) $ #$Revision: 271222 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/15/83/7158381.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_7158381 loop_ _publ_author_name 'Fuller, Rebecca O.' 'Taylor, Madeleine R.' 'Duggin, Margot' 'Bissember, Alex C.' 'Canty, Allan J.' 'Judd, Martyna M.' 'Cox, Nicholas' 'Moggach, Stephen A.' 'Turner, Gemma F.' _publ_section_title ; Enhanced synthesis of oxo-verdazyl radicals bearing sterically-and electronically-diverse C3-substituents. ; _journal_issue 46 _journal_name_full 'Organic & biomolecular chemistry' _journal_page_first 10120 _journal_page_last 10138 _journal_paper_doi 10.1039/d1ob01946e _journal_volume 19 _journal_year 2021 _chemical_formula_moiety 'C9 H13 N5 O' _chemical_formula_sum 'C9 H13 N5 O' _chemical_formula_weight 207.24 _chemical_name_common 1,5-dimethyl-3-pyridyl-oxoverdazyl _chemical_name_systematic 1,5-dimethyl-3-pyridyl-oxoverdazyl _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 2020-09-03 _audit_creation_method ; Olex2 1.3 (compiled 2020.07.31 svn.rc2a77460 for OlexSys, GUI svn.r6145) ; _audit_update_record ; 2021-09-30 deposited with the CCDC. 2021-11-01 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 124.601(2) _cell_angle_gamma 90 _cell_formula_units_Z 8 _cell_length_a 19.7981(3) _cell_length_b 7.60210(10) _cell_length_c 16.1604(3) _cell_measurement_reflns_used 17950 _cell_measurement_temperature 99.9(3) _cell_measurement_theta_max 74.0140 _cell_measurement_theta_min 3.2810 _cell_volume 2002.05(7) _computing_cell_refinement 'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)' _computing_data_collection 'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)' _computing_data_reduction 'CrysAlisPro 1.171.40.53 (Rigaku OD, 2019)' _computing_molecular_graphics 'Olex2 1.3 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.3 (Dolomanov et al., 2009)' _computing_structure_refinement 'SHELXL 2018/3 (Sheldrick, 2015)' _computing_structure_solution 'SHELXT 2018/2 (Sheldrick, 2018)' _diffrn_ambient_environment N~2~ _diffrn_ambient_temperature 99.9(3) _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 10.0000 _diffrn_detector_type HyPix _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.979 _diffrn_measurement_details ; List of Runs (angles in degrees, time in seconds): # Type Start End Width t~exp~ \w \q \k \f Frames #-------------------------------------------------------------------------- 1 \w 24.00 118.00 0.50 0.05 -- 46.20 77.00 -90.00 188 2 \w 24.00 118.00 0.50 0.05 -- 46.20 77.00-150.00 188 3 \w 24.00 118.00 0.50 0.05 -- 46.20 77.00 -60.00 188 4 \w 24.00 118.00 0.50 0.05 -- 46.20 77.00 0.00 188 5 \w 34.00 119.00 0.50 0.05 -- 46.20 38.00 -60.00 170 6 \w 24.00 118.00 0.50 0.05 -- 46.20 77.00 60.00 188 7 \w 31.00 118.00 0.50 0.05 -- 46.20 57.00 120.00 174 8 \w 24.00 118.00 0.50 0.05 -- 46.20 77.00 150.00 188 9 \w 34.00 119.00 0.50 0.05 -- 46.20 38.00 90.00 170 10 \w 34.00 121.00 0.50 0.05 -- 46.20 19.00-120.00 174 11 \w -71.00 -30.00 0.50 0.17 -- -102.41 61.00 0.00 82 12 \w -71.00 -30.00 0.50 0.17 -- -102.41 61.00-120.00 82 13 \w -71.00 -30.00 0.50 0.17 -- -102.41 61.00-180.00 82 14 \w 90.00 174.00 0.50 0.17 -- 102.41 45.00-180.00 168 15 \w 80.00 175.00 0.50 0.17 -- 102.41 115.00-151.00 190 16 \w 46.00 118.00 0.50 0.05 -- 46.20 168.00 -7.00 144 17 \w -28.00 26.00 0.50 0.05 -- 46.20 -19.00 -90.00 108 18 \w 30.00 105.00 0.50 0.17 -- 102.41 -77.00 -90.00 150 19 \w -28.00 26.00 0.50 0.05 -- 46.20 -19.00 90.00 108 20 \w -28.00 26.00 0.50 0.05 -- 46.20 -19.00 150.00 108 21 \w 30.00 71.00 0.50 0.17 -- 102.41 -61.00 120.00 82 22 \w 30.00 105.00 0.50 0.17 -- 102.41 -94.00 120.00 150 23 \w 30.00 108.00 0.50 0.17 -- 102.41-115.00 119.00 156 24 \w 6.00 89.00 0.50 0.05 -- 46.20-115.00 119.00 166 25 \w 35.00 142.00 0.50 0.17 -- 102.41-168.00 -25.00 214 26 \w 30.00 105.00 0.50 0.17 -- 102.41 -94.00-180.00 150 27 \w -141.00 -34.00 0.50 0.17 -- -102.41 168.00 -7.00 214 28 \w -111.00 -30.00 0.50 0.17 -- -102.41 125.00 0.00 162 29 \w -108.00 -30.00 0.50 0.17 -- -102.41 115.00-151.00 156 30 \w -108.00 -30.00 0.50 0.17 -- -102.41 110.00 -70.58 156 31 \w -89.00 -6.00 0.50 0.05 -- -46.20 115.00-151.00 166 32 \w -174.00 -90.00 0.50 0.17 -- -102.41 -45.00 -60.00 168 33 \w -175.00 -80.00 0.50 0.17 -- -102.41 -77.00 -60.00 190 34 \w -175.00 -80.00 0.50 0.17 -- -102.41 -77.00-150.00 190 35 \w -175.00 -80.00 0.50 0.17 -- -102.41 -75.00 34.71 190 36 \w -175.00 -81.00 0.50 0.17 -- -102.41 -74.00-127.16 188 37 \w -175.00 -83.00 0.50 0.17 -- -102.41 -68.00 150.46 184 38 \w -175.00 -85.00 0.50 0.17 -- -102.41 -63.00 -96.71 180 39 \w -175.00 -86.00 0.50 0.17 -- -102.41 -62.00 9.94 178 40 \w -175.00 -86.00 0.50 0.17 -- -102.41 -61.00 60.00 178 41 \w -175.00 -86.00 0.50 0.17 -- -102.41 -61.00 120.00 178 42 \w -175.00 -86.00 0.50 0.17 -- -102.41 -61.00 -30.00 178 43 \w -175.00 -86.00 0.50 0.17 -- -102.41 -61.00-180.00 178 44 \w -175.00-143.00 0.50 0.17 -- -102.41 -58.00 80.01 64 45 \w -175.00 -89.00 0.50 0.17 -- -102.41 -50.00 140.24 172 46 \w -175.00 -88.00 0.50 0.17 -- -102.41 -48.00 -24.21 174 47 \w -175.00 -90.00 0.50 0.17 -- -102.41 -46.00 81.89 170 48 \w -174.00 -90.00 0.50 0.17 -- -102.41 -45.00 30.00 168 49 \w -174.00 -90.00 0.50 0.17 -- -102.41 -45.00-130.87 168 50 \w -118.00 -46.00 0.50 0.05 -- -46.20-168.00 -25.00 144 51 \w -118.00 -73.00 0.50 0.05 -- -46.20-125.00 -30.00 90 52 \w -118.00 -73.00 0.50 0.05 -- -46.20-125.00-150.00 90 53 \w -118.00 -73.00 0.50 0.05 -- -46.20-125.00-180.00 90 54 \w -175.00 -80.00 0.50 0.17 -- -102.41-115.00 119.00 190 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'XtaLAB Synergy, Single source at home/near, HyPix' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 0.0169793000 _diffrn_orient_matrix_UB_12 0.1921504000 _diffrn_orient_matrix_UB_13 -0.0130707000 _diffrn_orient_matrix_UB_21 0.0036337000 _diffrn_orient_matrix_UB_22 -0.0551930000 _diffrn_orient_matrix_UB_23 -0.0891551000 _diffrn_orient_matrix_UB_31 -0.0929207000 _diffrn_orient_matrix_UB_32 0.0329782000 _diffrn_orient_matrix_UB_33 -0.0727806000 _diffrn_radiation_monochromator mirror _diffrn_radiation_probe x-ray _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0641 _diffrn_reflns_av_unetI/netI 0.0199 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.979 _diffrn_reflns_limit_h_max 24 _diffrn_reflns_limit_h_min -24 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_number 28970 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.979 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 75.623 _diffrn_reflns_theta_min 5.429 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'PhotonJet (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 0.794 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.68333 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro 1.171.40.53 (Rigaku Oxford Diffraction, 2019) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour 'clear light colourless' _exptl_crystal_density_diffrn 1.375 _exptl_crystal_description block _exptl_crystal_F_000 880 _exptl_crystal_size_max 0.19 _exptl_crystal_size_mid 0.171 _exptl_crystal_size_min 0.113 _refine_diff_density_max 0.275 _refine_diff_density_min -0.277 _refine_diff_density_rms 0.047 _refine_ls_extinction_coef 0.00074(15) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method 'SHELXL-2018/3 (Sheldrick 2018)' _refine_ls_goodness_of_fit_ref 1.084 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 139 _refine_ls_number_reflns 2042 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.084 _refine_ls_R_factor_all 0.0401 _refine_ls_R_factor_gt 0.0388 _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^)+(0.0534P)^2^+1.7124P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1038 _refine_ls_wR_factor_ref 0.1050 _reflns_Friedel_coverage 0.000 _reflns_number_gt 1937 _reflns_number_total 2042 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d1ob01946e2.cif _cod_data_source_block 9c _cod_depositor_comments 'Adding full bibliography for 7158376--7158384.cif.' _cod_database_code 7158381 _chemical_oxdiff_formula 'C9 H13 N5 O' _chemical_oxdiff_usercomment 'Becky UTas' _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 100.00 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 66.49 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All N(H) groups At 1.5 times of: All C(H,H,H) groups 2.a Riding coordinates: N003(H003), N005(H005) 2.b Ternary CH refined with riding coordinates: C00A(H00A) 2.c Aromatic/amide H refined with riding coordinates: C008(H008), C00B(H00B), C00C(H00C), C00D(H00D) 2.d Idealised Me refined as rotating group: C00E(H00E,H00F,H00G), C00F(H00H,H00I,H00J) ; _shelx_res_file ; TITL bof4_a.res in C2/c bof4.res created by SHELXL-2018/3 at 14:10:01 on 03-Sep-2020 REM Old TITL BOF4 in C2/c REM SHELXT solution in C2/c: R1 0.138, Rweak 0.011, Alpha 0.021 REM 0.673 for 161 systematic absences, Orientation as input REM Formula found by SHELXT: C11 N3 O CELL 1.54184 19.7981 7.6021 16.1604 90 124.601 90 ZERR 8 0.0003 0.0001 0.0003 0 0.002 0 LATT 7 SYMM -X,+Y,0.5-Z SFAC C H N O UNIT 72 104 40 8 L.S. 4 0 0 PLAN 5 CONF BOND list 4 fmap 2 53 MORE -1 BOND $H ACTA REM REM REM WGHT 0.053400 1.712400 EXTI 0.000739 FVAR 0.29440 O001 4 0.641544 0.653470 0.695645 11.00000 0.02078 0.02839 = 0.02585 0.00248 0.01042 -0.00609 N002 3 0.599364 0.369725 0.675406 11.00000 0.01583 0.02247 = 0.02740 0.00222 0.01279 -0.00008 N003 3 0.535754 0.244930 0.645370 11.00000 0.01642 0.01903 = 0.02221 0.00251 0.01082 0.00007 AFIX 3 H003 2 0.539434 0.191920 0.694790 11.00000 -1.20000 AFIX 0 N004 3 0.388645 0.157626 0.634387 11.00000 0.01851 0.02246 = 0.02211 -0.00204 0.01193 -0.00090 N005 3 0.443566 0.488578 0.613019 11.00000 0.01632 0.01881 = 0.02768 -0.00338 0.01141 -0.00201 AFIX 3 H005 2 0.427136 0.471418 0.651509 11.00000 -1.20000 AFIX 0 N006 3 0.513626 0.601342 0.656311 11.00000 0.01859 0.01783 = 0.03064 -0.00411 0.01152 -0.00299 C007 1 0.389454 0.198056 0.554155 11.00000 0.01685 0.01600 = 0.02159 0.00051 0.00969 0.00283 C008 1 0.333443 0.131221 0.458837 11.00000 0.02154 0.02163 = 0.02025 0.00092 0.00933 0.00009 AFIX 43 H008 2 0.336718 0.160402 0.405326 11.00000 -1.20000 AFIX 0 C009 1 0.587545 0.546213 0.676260 11.00000 0.01807 0.02382 = 0.01520 0.00181 0.00768 -0.00176 C00A 1 0.455940 0.325584 0.575056 11.00000 0.01790 0.01775 = 0.01876 0.00014 0.00933 0.00028 AFIX 13 H00A 2 0.450414 0.350744 0.511997 11.00000 -1.20000 AFIX 0 C00B 1 0.329423 0.049066 0.619757 11.00000 0.02189 0.02590 = 0.02697 -0.00139 0.01603 -0.00131 AFIX 43 H00B 2 0.328236 0.019484 0.674759 11.00000 -1.20000 AFIX 0 C00C 1 0.269937 -0.021253 0.526936 11.00000 0.01815 0.02140 = 0.03176 -0.00235 0.01385 -0.00206 AFIX 43 H00C 2 0.229249 -0.094408 0.519702 11.00000 -1.20000 AFIX 0 C00D 1 0.272265 0.019569 0.445099 11.00000 0.01985 0.02217 = 0.02319 -0.00276 0.00709 -0.00148 AFIX 43 H00D 2 0.233540 -0.026945 0.381992 11.00000 -1.20000 AFIX 0 C00E 1 0.668197 0.305202 0.674649 11.00000 0.02089 0.03323 = 0.03667 0.00205 0.01890 0.00243 AFIX 137 H00E 2 0.690085 0.201131 0.715271 11.00000 -1.50000 H00F 2 0.710031 0.393952 0.701250 11.00000 -1.50000 H00G 2 0.649892 0.277951 0.606925 11.00000 -1.50000 AFIX 0 C00F 1 0.492193 0.786613 0.632308 11.00000 0.02802 0.01882 = 0.04802 -0.00383 0.01646 -0.00094 AFIX 137 H00H 2 0.475527 0.808923 0.564711 11.00000 -1.50000 H00I 2 0.539008 0.858003 0.678007 11.00000 -1.50000 H00J 2 0.447937 0.814858 0.638407 11.00000 -1.50000 AFIX 0 HKLF 4 REM bof4_a.res in C2/c REM wR2 = 0.1050, GooF = S = 1.084, Restrained GooF = 1.084 for all data REM R1 = 0.0388 for 1937 Fo > 4sig(Fo) and 0.0401 for all 2042 data REM 139 parameters refined using 0 restraints END WGHT 0.0533 1.7216 REM Highest difference peak 0.275, deepest hole -0.277, 1-sigma level 0.047 Q1 1 0.6607 0.1762 0.6553 11.00000 0.05 0.27 Q2 1 0.4176 0.2573 0.5643 11.00000 0.05 0.27 Q3 1 0.4541 0.4330 0.6843 11.00000 0.05 0.25 Q4 1 0.7141 0.2848 0.7489 11.00000 0.05 0.22 Q5 1 0.3550 0.1723 0.5075 11.00000 0.05 0.21 ; _shelx_res_checksum 53912 _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 1.601 _oxdiff_exptl_absorpt_empirical_full_min 0.699 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 O001 O 0.64154(5) 0.65347(12) 0.69564(7) 0.0266(2) Uani 1 1 d . . . . . N002 N 0.59936(6) 0.36972(14) 0.67541(8) 0.0216(3) Uani 1 1 d . . . . . N003 N 0.53575(6) 0.24493(13) 0.64537(8) 0.0193(2) Uani 1 1 d . . . . . H003 H 0.539434 0.191920 0.694790 0.023 Uiso 1 1 d R U . . . N004 N 0.38864(6) 0.15763(14) 0.63439(8) 0.0208(2) Uani 1 1 d . . . . . N005 N 0.44357(6) 0.48858(13) 0.61302(8) 0.0215(3) Uani 1 1 d . . . . . H005 H 0.427136 0.471418 0.651509 0.026 Uiso 1 1 d R U . . . N006 N 0.51363(6) 0.60134(14) 0.65631(8) 0.0237(3) Uani 1 1 d . . . . . C007 C 0.38945(7) 0.19806(15) 0.55415(9) 0.0188(3) Uani 1 1 d . . . . . C008 C 0.33344(8) 0.13122(16) 0.45884(9) 0.0226(3) Uani 1 1 d . . . . . H008 H 0.336718 0.160402 0.405326 0.027 Uiso 1 1 calc R U . . . C009 C 0.58754(7) 0.54621(16) 0.67626(8) 0.0200(3) Uani 1 1 d . . . . . C00A C 0.45594(7) 0.32558(15) 0.57506(9) 0.0187(3) Uani 1 1 d . . . . . H00A H 0.450414 0.350744 0.511997 0.022 Uiso 1 1 calc R U . . . C00B C 0.32942(8) 0.04907(17) 0.61976(10) 0.0237(3) Uani 1 1 d . . . . . H00B H 0.328236 0.019484 0.674759 0.028 Uiso 1 1 calc R U . . . C00C C 0.26994(7) -0.02125(17) 0.52694(10) 0.0239(3) Uani 1 1 d . . . . . H00C H 0.229249 -0.094408 0.519702 0.029 Uiso 1 1 calc R U . . . C00D C 0.27227(8) 0.01957(17) 0.44510(10) 0.0246(3) Uani 1 1 d . . . . . H00D H 0.233540 -0.026945 0.381992 0.030 Uiso 1 1 calc R U . . . C00E C 0.66820(8) 0.30520(19) 0.67465(11) 0.0288(3) Uani 1 1 d . . . . . H00E H 0.690085 0.201131 0.715271 0.043 Uiso 1 1 calc R U . . . H00F H 0.710031 0.393952 0.701250 0.043 Uiso 1 1 calc R U . . . H00G H 0.649892 0.277951 0.606925 0.043 Uiso 1 1 calc R U . . . C00F C 0.49219(9) 0.78661(17) 0.63231(12) 0.0345(3) Uani 1 1 d . . . . . H00H H 0.475527 0.808923 0.564711 0.052 Uiso 1 1 calc R U . . . H00I H 0.539008 0.858003 0.678007 0.052 Uiso 1 1 calc R U . . . H00J H 0.447937 0.814858 0.638407 0.052 Uiso 1 1 calc R U . . . 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 0.0208(5) 0.0284(5) 0.0258(5) 0.0025(4) 0.0104(4) -0.0061(4) N002 0.0158(5) 0.0225(5) 0.0274(5) 0.0022(4) 0.0128(4) -0.0001(4) N003 0.0164(5) 0.0190(5) 0.0222(5) 0.0025(4) 0.0108(4) 0.0001(4) N004 0.0185(5) 0.0225(5) 0.0221(5) -0.0020(4) 0.0119(4) -0.0009(4) N005 0.0163(5) 0.0188(5) 0.0277(5) -0.0034(4) 0.0114(4) -0.0020(4) N006 0.0186(5) 0.0178(5) 0.0306(6) -0.0041(4) 0.0115(4) -0.0030(4) C007 0.0168(6) 0.0160(5) 0.0216(6) 0.0005(4) 0.0097(5) 0.0028(4) C008 0.0215(6) 0.0216(6) 0.0202(6) 0.0009(5) 0.0093(5) 0.0001(5) C009 0.0181(6) 0.0238(6) 0.0152(5) 0.0018(4) 0.0077(5) -0.0018(5) C00A 0.0179(6) 0.0177(6) 0.0188(6) 0.0001(4) 0.0093(5) 0.0003(4) C00B 0.0219(6) 0.0259(6) 0.0270(6) -0.0014(5) 0.0160(5) -0.0013(5) C00C 0.0181(6) 0.0214(6) 0.0318(7) -0.0023(5) 0.0139(5) -0.0021(5) C00D 0.0199(6) 0.0222(6) 0.0232(6) -0.0028(5) 0.0071(5) -0.0015(5) C00E 0.0209(6) 0.0332(7) 0.0367(7) 0.0020(6) 0.0189(6) 0.0024(5) C00F 0.0280(7) 0.0188(6) 0.0480(8) -0.0038(6) 0.0165(7) -0.0009(5) 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 7 3 2 0.1116 1 5 1 0.1217 -7 4 0 0.0772 -2 -5 -1 0.0153 -1 0 9 0.0548 12 -1 -9 0.0824 1 0 -9 0.0574 -12 1 8 0.0407 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 N003 N002 C00E 115.08(10) . . ? C009 N002 N003 122.38(10) . . ? C009 N002 C00E 119.92(11) . . ? N002 N003 H003 113.8 . . ? N002 N003 C00A 110.05(9) . . ? C00A N003 H003 113.8 . . ? C00B N004 C007 117.38(10) . . ? N006 N005 H005 113.4 . . ? N006 N005 C00A 111.45(9) . . ? C00A N005 H005 113.4 . . ? N005 N006 C00F 113.19(10) . . ? C009 N006 N005 122.69(10) . . ? C009 N006 C00F 117.87(11) . . ? N004 C007 C008 123.31(11) . . ? N004 C007 C00A 114.72(10) . . ? C008 C007 C00A 121.97(11) . . ? C007 C008 H008 120.8 . . ? C007 C008 C00D 118.44(11) . . ? C00D C008 H008 120.8 . . ? O001 C009 N002 121.56(11) . . ? O001 C009 N006 120.77(11) . . ? N002 C009 N006 117.66(11) . . ? N003 C00A N005 113.25(10) . . ? N003 C00A C007 109.00(9) . . ? N003 C00A H00A 108.9 . . ? N005 C00A C007 107.76(9) . . ? N005 C00A H00A 108.9 . . ? C007 C00A H00A 108.9 . . ? N004 C00B H00B 118.3 . . ? N004 C00B C00C 123.34(11) . . ? C00C C00B H00B 118.3 . . ? C00B C00C H00C 120.7 . . ? C00B C00C C00D 118.63(11) . . ? C00D C00C H00C 120.7 . . ? C008 C00D H00D 120.6 . . ? C00C C00D C008 118.89(11) . . ? C00C C00D H00D 120.6 . . ? N002 C00E H00E 109.5 . . ? N002 C00E H00F 109.5 . . ? N002 C00E H00G 109.5 . . ? H00E C00E H00F 109.5 . . ? H00E C00E H00G 109.5 . . ? H00F C00E H00G 109.5 . . ? N006 C00F H00H 109.5 . . ? N006 C00F H00I 109.5 . . ? N006 C00F H00J 109.5 . . ? H00H C00F H00I 109.5 . . ? H00H C00F H00J 109.5 . . ? H00I C00F H00J 109.5 . . ? 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 C009 1.2351(15) . ? N002 N003 1.4239(14) . ? N002 C009 1.3633(16) . ? N002 C00E 1.4549(15) . ? N003 H003 0.8599 . ? N003 C00A 1.4577(15) . ? N004 C007 1.3414(16) . ? N004 C00B 1.3405(16) . ? N005 H005 0.8600 . ? N005 N006 1.4304(14) . ? N005 C00A 1.4637(15) . ? N006 C009 1.3731(16) . ? N006 C00F 1.4585(17) . ? C007 C008 1.3859(17) . ? C007 C00A 1.5105(16) . ? C008 H008 0.9300 . ? C008 C00D 1.3897(18) . ? C00A H00A 0.9800 . ? C00B H00B 0.9300 . ? C00B C00C 1.3844(18) . ? C00C H00C 0.9300 . ? C00C C00D 1.3845(19) . ? C00D H00D 0.9300 . ? C00E H00E 0.9600 . ? C00E H00F 0.9600 . ? C00E H00G 0.9600 . ? C00F H00H 0.9600 . ? C00F H00I 0.9600 . ? C00F H00J 0.9600 . ? loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_site_symmetry_1 _geom_torsion_site_symmetry_2 _geom_torsion_site_symmetry_3 _geom_torsion_site_symmetry_4 _geom_torsion_publ_flag N002 N003 C00A N005 -53.27(13) . . . . ? N002 N003 C00A C007 -173.21(9) . . . . ? N003 N002 C009 O001 -174.80(10) . . . . ? N003 N002 C009 N006 6.23(17) . . . . ? N004 C007 C008 C00D 1.39(18) . . . . ? N004 C007 C00A N003 63.49(13) . . . . ? N004 C007 C00A N005 -59.78(13) . . . . ? N004 C00B C00C C00D 1.21(19) . . . . ? N005 N006 C009 O001 166.32(11) . . . . ? N005 N006 C009 N002 -14.69(17) . . . . ? N006 N005 C00A N003 45.97(13) . . . . ? N006 N005 C00A C007 166.61(9) . . . . ? C007 N004 C00B C00C -0.26(18) . . . . ? C007 C008 C00D C00C -0.38(18) . . . . ? C008 C007 C00A N003 -117.38(12) . . . . ? C008 C007 C00A N005 119.35(12) . . . . ? C009 N002 N003 C00A 27.14(15) . . . . ? C00A N005 N006 C009 -11.62(15) . . . . ? C00A N005 N006 C00F 139.93(12) . . . . ? C00A C007 C008 C00D -177.66(11) . . . . ? C00B N004 C007 C008 -1.07(17) . . . . ? C00B N004 C007 C00A 178.05(10) . . . . ? C00B C00C C00D C008 -0.84(18) . . . . ? C00E N002 N003 C00A -134.45(11) . . . . ? C00E N002 C009 O001 -14.06(18) . . . . ? C00E N002 C009 N006 166.96(11) . . . . ? C00F N006 C009 O001 16.02(17) . . . . ? C00F N006 C009 N002 -165.00(12) . . . . ? 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 7.2175 2.9605 1.5756 0.6708 -0.2776 -0.6877 1.2207 4.7855 1.3775 0.9223 -0.3825 -0.0559 -7.2333 3.6407 0.1342 0.5750 -0.2392 0.7824 -1.9704 -4.6882 -1.4362 -0.9155 0.3796 0.1330 -1.3426 -0.0533 9.2078 -0.1534 -0.8229 -0.5472 11.5133 -0.7750 -8.9213 0.1632 0.8800 -0.4461 1.2274 0.0618 -9.1620 0.1525 0.8179 0.5548 -12.3119 0.8617 7.6646 -0.1436 -0.7756 0.6146