#------------------------------------------------------------------------------ #$Date: 2026-06-25 00:07:02 +0100 (Thu, 25 Jun 2026) $ #$Revision: 306639 $ #$URL: svn://www.crystallography.net/cod/cif/1/57/74/1577430.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_1577430 loop_ _publ_author_name 'Schiele, Stefanie' 'Paschke, Ann-Sophie K.' 'Romiti, Giorgia' 'Morandi, Bill' _publ_section_title ; Direct access to 2-imidazolines from unactivated alkenes ; _journal_name_full 'Chemical Science' _journal_paper_doi 10.1039/D6SC03337G _journal_year 2026 _chemical_formula_moiety 'Cl, C10 H13 N2' _chemical_formula_sum 'C10 H13 Cl N2' _chemical_formula_weight 196.67 _chemical_name_systematic '2-Benzyl-4,5-dihydro-1H-imidazole (HCl salt)' _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 mixed _atom_sites_solution_primary dual _audit_creation_date 2025-10-23 _audit_creation_method ; Olex2 1.5 (compiled 2025.07.13 svn.rb7424aed for OlexSys, GUI svn.r7314) ; _audit_update_record ; 2026-02-05 deposited with the CCDC. 2026-06-09 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 103.098(2) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 8.8392(2) _cell_length_b 9.44990(10) _cell_length_c 12.2464(2) _cell_measurement_reflns_used 13647 _cell_measurement_temperature 100.0(1) _cell_measurement_theta_max 78.3430 _cell_measurement_theta_min 5.1120 _cell_volume 996.32(3) _computing_cell_refinement 'CrysAlisPro 1.171.43.144a (Rigaku OD, 2024)' _computing_data_collection 'CrysAlisPro system (CCD 43.144a 64-bit (release 23-01-2025))' _computing_data_reduction 'CrysAlisPro 1.171.43.144a (Rigaku OD, 2024)' _computing_molecular_graphics 'Olex2 1.5 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.5 (Dolomanov et al., 2009)' _computing_structure_refinement 'SHELXL 2019/3 (Sheldrick, 2015)' _computing_structure_solution 'SHELXT 2018/2 (Sheldrick, 2018)' _diffrn_ambient_environment N~2~ _diffrn_ambient_temperature 100.0(1) _diffrn_detector 'Hybrid Pixel Array Detector' _diffrn_detector_area_resol_mean 5.8140 _diffrn_detector_type 'Pilatus 300K' _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.964 _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 -9.00 27.00 0.50 0.10 -- -49.37 19.00-150.00 72 2 \w -9.00 27.00 0.50 0.10 -- -49.37 19.00-120.00 72 3 \w -9.00 27.00 0.50 0.10 -- -49.37 19.00 -60.00 72 4 \w -9.00 27.00 0.50 0.10 -- -49.37 19.00 -90.00 72 5 \w -9.00 27.00 0.50 0.10 -- -49.37 19.00 30.00 72 6 \w -9.00 27.00 0.50 0.10 -- -49.37 19.00 90.00 72 7 \w -68.00 -17.00 0.50 0.30 -- -88.50 57.00 0.00 102 8 \w -68.00 -17.00 0.50 0.30 -- -88.50 57.00 -30.00 102 9 \w -68.00 -17.00 0.50 0.30 -- -88.50 57.00-150.00 102 10 \w -68.00 -17.00 0.50 0.30 -- -88.50 57.00-180.00 102 11 \w -91.00 -15.00 0.50 0.10 -- -49.37 131.00 -74.00 152 12 \w -91.00 -15.00 0.50 0.10 -- -49.37 131.00 -74.00 152 13 \w -125.00 -36.00 0.50 0.10 -- -49.37 -19.00 -90.00 178 14 \w -125.00 -36.00 0.50 0.10 -- -49.37 -19.00 -90.00 178 15 \w -161.00 -74.00 0.50 0.30 -- -88.50 -53.00-110.51 174 16 \w -156.00 -67.00 0.50 0.30 -- -88.50 -71.00 34.86 178 17 \w -154.00 -65.00 0.50 0.30 -- -88.50 -77.00 150.00 178 18 \w -154.00 -65.00 0.50 0.30 -- -88.50 -77.00 150.00 178 19 \w -154.00 -66.00 0.50 0.30 -- -88.50 -74.00 157.74 176 20 \w -154.00 -66.00 0.50 0.30 -- -88.50 -74.00 157.74 176 21 \w -156.00 -67.00 0.50 0.30 -- -88.50 -71.00 34.86 178 22 \w -160.00 -72.00 0.50 0.30 -- -88.50 -58.00 41.78 176 23 \w -161.00 -74.00 0.50 0.30 -- -88.50 -53.00-110.51 174 24 \w -157.00 -85.00 0.50 0.30 -- -88.50 -99.00 -30.00 144 25 \w -157.00 -85.00 0.50 0.30 -- -88.50 -99.00 0.00 144 26 \w -157.00 -85.00 0.50 0.30 -- -88.50 -99.00 -60.00 144 27 \w 45.00 77.00 0.50 0.30 -- 110.00-125.00-180.00 64 28 \w 41.00 113.00 0.50 0.30 -- 110.00-125.00 -90.00 144 29 \w 41.00 106.00 0.50 0.30 -- 110.00 -99.00-180.00 130 30 \w 72.00 97.00 0.50 0.30 -- 110.00 -99.00 -60.00 50 31 \w 41.00 113.00 0.50 0.30 -- 110.00-125.00 90.00 144 32 \w 45.00 107.00 0.50 0.30 -- 110.00-104.00 108.00 124 33 \w -26.00 9.00 0.50 0.10 -- 49.37 -19.00 -30.00 70 34 \w 38.00 68.00 0.50 0.30 -- 110.00 -57.00 150.00 60 35 \w 38.00 65.00 0.50 0.30 -- 110.00 -57.00 30.00 54 36 \w 38.00 68.00 0.50 0.30 -- 110.00 -57.00 -60.00 60 37 \w 38.00 68.00 0.50 0.30 -- 110.00 -57.00-180.00 60 38 \w 98.00 178.00 0.50 0.30 -- 110.00 38.00-180.00 160 39 \w 94.00 178.00 0.50 0.30 -- 110.00 125.00 30.00 168 40 \w 62.00 121.00 0.50 0.10 -- 49.37 178.00 150.00 118 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'XtaLAB Synergy, Dualflex, Pilatus 300K' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 0.0576273000 _diffrn_orient_matrix_UB_12 -0.1467755000 _diffrn_orient_matrix_UB_13 0.0462345000 _diffrn_orient_matrix_UB_21 0.0174171000 _diffrn_orient_matrix_UB_22 0.0552605000 _diffrn_orient_matrix_UB_23 0.1205757000 _diffrn_orient_matrix_UB_31 -0.1685218000 _diffrn_orient_matrix_UB_32 -0.0444481000 _diffrn_orient_matrix_UB_33 -0.0028357000 _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 0.0510 _diffrn_reflns_av_unetI/netI 0.0256 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.964 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -15 _diffrn_reflns_number 18567 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.964 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 79.699 _diffrn_reflns_theta_min 5.137 _diffrn_source 'micro-focus sealed X-ray tube' _diffrn_source_type 'PhotonJet (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 3.008 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_correction_T_min 0.717 _exptl_absorpt_correction_type gaussian _exptl_absorpt_process_details ; CrysAlisPro 1.171.43.144a (Rigaku Oxford Diffraction, 2024) Numerical absorption correction based on gaussian integration over a multifaceted crystal model Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour 'clear light yellow' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_modifier light _exptl_crystal_colour_primary yellow _exptl_crystal_density_diffrn 1.311 _exptl_crystal_description block _exptl_crystal_F_000 416 _exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: acetonitrile' _exptl_crystal_size_max 0.139 _exptl_crystal_size_mid 0.123 _exptl_crystal_size_min 0.047 _refine_diff_density_max 0.194 _refine_diff_density_min -0.354 _refine_diff_density_rms 0.055 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.058 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 124 _refine_ls_number_reflns 2090 _refine_ls_number_restraints 2 _refine_ls_restrained_S_all 1.059 _refine_ls_R_factor_all 0.0355 _refine_ls_R_factor_gt 0.0332 _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^)+(0.0529P)^2^+0.3932P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0912 _refine_ls_wR_factor_ref 0.0936 _reflns_Friedel_coverage 0.000 _reflns_number_gt 1934 _reflns_number_total 2090 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d6sc03337g2.cif _cod_data_source_block bm231025_1_1 _cod_database_code 1577430 _shelx_shelxl_version_number 2019/3 _chemical_oxdiff_formula C10H12N2 _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 0.864 _shelx_estimated_absorpt_t_min 0.678 _diffrn_oxdiff_ac3_digest_hkl 01b0dcba3c54762e1af188ad48a156a49a95ab _diffrn_oxdiff_digest_hkl ; 4351b3c4d45098589453a0f35df48e66d5b3be ; _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups, All C(H,H) groups, All N(H) groups 2. Restrained distances N2-H2 = N1-H1 0.93 with sigma of 0.02 3.a Secondary CH2 refined with riding coordinates: C2(H2A,H2B), C3(H3A,H3B), C4(H4A,H4B) 3.b Aromatic/amide H refined with riding coordinates: C6(H6), C7(H7), C10(H10), C8(H8), C9(H9) ; _shelx_res_file ; TITL bm231025_1_1_a.res in P2(1)/c bm231025_1_1.res created by SHELXL-2019/3 at 15:37:31 on 23-Oct-2025 REM Old TITL bm231025_1_1 in P21/c #14 REM SHELXT solution in P2(1)/c: R1 0.089, Rweak 0.033, Alpha 0.018 REM 0.413 for 133 systematic absences, Orientation as input REM Formula found by SHELXT: C10 N2 Cl CELL 1.54184 8.8392 9.4499 12.2464 90 103.098 90 ZERR 4 0.0002 0.0001 0.0002 0 0.002 0 LATT 1 SYMM -X,0.5+Y,0.5-Z SFAC C H Cl N UNIT 40 52 4 8 DFIX 0.93 N2 H2 N1 H1 L.S. 8 PLAN 10 SIZE 0.05 0.12 0.14 TEMP -173 CONF BOND list 4 fmap 2 ACTA MORE -1 BOND $H OMIT 0 6 13 REM REM REM WGHT 0.052900 0.393200 FVAR 0.61872 CL1 3 0.628301 0.214441 0.548873 11.00000 0.02259 0.02860 = 0.01995 0.00361 0.00300 0.00398 N1 4 0.309769 0.582199 0.713299 11.00000 0.02287 0.02623 = 0.01992 -0.00448 0.00335 -0.00147 H1 2 0.314682 0.624730 0.779696 11.00000 -1.20000 N2 4 0.387301 0.434778 0.599867 11.00000 0.02252 0.02516 = 0.02222 -0.00290 0.00438 0.00195 H2 2 0.450386 0.372203 0.576106 11.00000 -1.20000 C5 1 0.697355 0.579179 0.776069 11.00000 0.02127 0.02301 = 0.02077 -0.00401 0.00335 0.00239 C1 1 0.421026 0.497815 0.697739 11.00000 0.02255 0.02066 = 0.02037 0.00125 0.00456 -0.00306 C2 1 0.176991 0.579120 0.616648 11.00000 0.01965 0.02952 = 0.02282 -0.00196 0.00355 -0.00021 AFIX 23 H2A 2 0.157913 0.673502 0.581108 11.00000 -1.20000 H2B 2 0.081596 0.546591 0.638562 11.00000 -1.20000 AFIX 0 C3 1 0.229847 0.471731 0.537763 11.00000 0.02093 0.02920 = 0.02220 -0.00354 0.00248 -0.00323 AFIX 23 H3A 2 0.161416 0.387550 0.525421 11.00000 -1.20000 H3B 2 0.231329 0.515207 0.464463 11.00000 -1.20000 AFIX 0 C6 1 0.681847 0.684946 0.695415 11.00000 0.02245 0.02452 = 0.02281 -0.00281 0.00363 0.00233 AFIX 43 H6 2 0.586266 0.696003 0.641967 11.00000 -1.20000 AFIX 0 C4 1 0.568741 0.475403 0.782888 11.00000 0.02462 0.02525 = 0.02389 0.00334 -0.00074 -0.00006 AFIX 23 H4A 2 0.606367 0.378305 0.774158 11.00000 -1.20000 H4B 2 0.546745 0.482041 0.858472 11.00000 -1.20000 AFIX 0 C7 1 0.806068 0.774971 0.692608 11.00000 0.03046 0.02558 = 0.02989 -0.00361 0.01196 -0.00011 AFIX 43 H7 2 0.794739 0.847125 0.637329 11.00000 -1.20000 AFIX 0 C10 1 0.838349 0.565007 0.854126 11.00000 0.02623 0.03311 = 0.02677 -0.00061 0.00010 0.00383 AFIX 43 H10 2 0.849921 0.493568 0.909987 11.00000 -1.20000 AFIX 0 C8 1 0.946171 0.759374 0.770384 11.00000 0.02449 0.03442 = 0.03911 -0.01188 0.01294 -0.00550 AFIX 43 H8 2 1.030842 0.820470 0.768359 11.00000 -1.20000 AFIX 0 C9 1 0.961733 0.654200 0.850937 11.00000 0.02225 0.04369 = 0.03400 -0.00704 -0.00045 0.00046 AFIX 43 H9 2 1.057436 0.643150 0.904253 11.00000 -1.20000 AFIX 0 HKLF 4 REM bm231025_1_1_a.res in P2(1)/c REM wR2 = 0.0936, GooF = S = 1.058, Restrained GooF = 1.059 for all data REM R1 = 0.0332 for 1934 Fo > 4sig(Fo) and 0.0355 for all 2090 data REM 124 parameters refined using 2 restraints END WGHT 0.0528 0.3942 REM Highest difference peak 0.194, deepest hole -0.354, 1-sigma level 0.055 Q1 1 0.6365 0.5400 0.7810 11.00000 0.05 0.19 Q2 1 0.4878 0.4786 0.7380 11.00000 0.05 0.18 Q3 1 0.1994 0.5240 0.5797 11.00000 0.05 0.18 Q4 1 0.5000 0.5000 1.0000 10.50000 0.05 0.17 Q5 1 0.5713 0.5479 0.5572 11.00000 0.05 0.17 Q6 1 0.7472 0.5874 0.8212 11.00000 0.05 0.16 Q7 1 0.4636 0.4954 0.5187 11.00000 0.05 0.16 Q8 1 0.5667 0.1421 0.4601 11.00000 0.05 0.16 Q9 1 0.5391 0.2719 0.4566 11.00000 0.05 0.16 Q10 1 0.7566 0.1611 0.6222 11.00000 0.05 0.16 ; _shelx_res_checksum 15401 _olex2_date_sample_data_collection 2025-10-21 _olex2_date_sample_submission 2025-10-21 _olex2_submission_original_sample_id bm231025_1_1 _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 - Detector area scaling ; _oxdiff_exptl_absorpt_empirical_full_max 2.126 _oxdiff_exptl_absorpt_empirical_full_min 0.750 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 Cl1 Cl 0.62830(4) 0.21444(3) 0.54887(3) 0.02400(13) Uani 1 1 d . . . . . N1 N 0.30977(14) 0.58220(13) 0.71330(10) 0.0232(3) Uani 1 1 d D . . . . H1 H 0.315(2) 0.6247(18) 0.7797(12) 0.028 Uiso 1 1 d D U . . . N2 N 0.38730(14) 0.43478(13) 0.59987(10) 0.0234(3) Uani 1 1 d D . . . . H2 H 0.4504(19) 0.3722(18) 0.5761(15) 0.028 Uiso 1 1 d D U . . . C5 C 0.69735(16) 0.57918(14) 0.77607(11) 0.0219(3) Uani 1 1 d . . . . . C1 C 0.42103(16) 0.49781(14) 0.69774(11) 0.0212(3) Uani 1 1 d . . . . . C2 C 0.17699(16) 0.57912(16) 0.61665(12) 0.0242(3) Uani 1 1 d . . . . . H2A H 0.157913 0.673502 0.581108 0.029 Uiso 1 1 calc R U . . . H2B H 0.081596 0.546591 0.638562 0.029 Uiso 1 1 calc R U . . . C3 C 0.22985(16) 0.47173(16) 0.53776(12) 0.0245(3) Uani 1 1 d . . . . . H3A H 0.161416 0.387550 0.525421 0.029 Uiso 1 1 calc R U . . . H3B H 0.231329 0.515207 0.464463 0.029 Uiso 1 1 calc R U . . . C6 C 0.68185(17) 0.68495(15) 0.69542(12) 0.0235(3) Uani 1 1 d . . . . . H6 H 0.586266 0.696003 0.641967 0.028 Uiso 1 1 calc R U . . . C4 C 0.56874(17) 0.47540(16) 0.78289(12) 0.0256(3) Uani 1 1 d . . . . . H4A H 0.606367 0.378305 0.774158 0.031 Uiso 1 1 calc R U . . . H4B H 0.546745 0.482041 0.858472 0.031 Uiso 1 1 calc R U . . . C7 C 0.80607(19) 0.77497(16) 0.69261(14) 0.0278(3) Uani 1 1 d . . . . . H7 H 0.794739 0.847125 0.637329 0.033 Uiso 1 1 calc R U . . . C10 C 0.83835(18) 0.56501(17) 0.85413(13) 0.0296(3) Uani 1 1 d . . . . . H10 H 0.849921 0.493568 0.909987 0.036 Uiso 1 1 calc R U . . . C8 C 0.94617(19) 0.75937(18) 0.77038(14) 0.0318(4) Uani 1 1 d . . . . . H8 H 1.030842 0.820470 0.768359 0.038 Uiso 1 1 calc R U . . . C9 C 0.96173(18) 0.65420(19) 0.85094(14) 0.0344(4) Uani 1 1 d . . . . . H9 H 1.057436 0.643150 0.904253 0.041 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 Cl1 0.0226(2) 0.0286(2) 0.0199(2) 0.00361(11) 0.00300(13) 0.00398(12) N1 0.0229(6) 0.0262(6) 0.0199(6) -0.0045(5) 0.0033(5) -0.0015(5) N2 0.0225(6) 0.0252(6) 0.0222(6) -0.0029(5) 0.0044(5) 0.0020(5) C5 0.0213(7) 0.0230(7) 0.0208(6) -0.0040(5) 0.0034(5) 0.0024(5) C1 0.0225(7) 0.0207(6) 0.0204(6) 0.0012(5) 0.0046(5) -0.0031(5) C2 0.0197(7) 0.0295(7) 0.0228(7) -0.0020(5) 0.0035(5) -0.0002(5) C3 0.0209(7) 0.0292(7) 0.0222(7) -0.0035(6) 0.0025(5) -0.0032(5) C6 0.0225(7) 0.0245(7) 0.0228(7) -0.0028(5) 0.0036(5) 0.0023(5) C4 0.0246(7) 0.0252(7) 0.0239(7) 0.0033(5) -0.0007(5) -0.0001(5) C7 0.0305(8) 0.0256(7) 0.0299(8) -0.0036(6) 0.0120(6) -0.0001(6) C10 0.0262(8) 0.0331(8) 0.0268(7) -0.0006(6) 0.0001(6) 0.0038(6) C8 0.0245(8) 0.0344(8) 0.0391(9) -0.0119(7) 0.0129(7) -0.0055(6) C9 0.0223(7) 0.0437(10) 0.0340(8) -0.0070(7) -0.0005(6) 0.0005(6) 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' Cl Cl 0.3639 0.7018 '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' loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 0 0 1 0.0239 0 0 -1 0.0258 2 2 -1 0.0461 0 -2 1 0.0705 -2 1 0 0.0508 -2 -2 1 0.0951 2 1 -2 0.0527 -4 0 -4 0.0449 1 3 -7 0.0396 -3 -1 -6 0.0409 5 1 -5 0.0560 -5 -2 -2 0.0708 0 -3 -7 0.0315 2 -2 -7 0.0307 -2 2 7 0.0283 4 -1 -7 0.0480 0 -4 -5 0.0433 1 4 5 0.0330 2 -4 -6 0.0399 3 5 -2 0.0475 -2 2 -6 0.0369 2 -2 6 0.0369 3 3 -6 0.0397 0 -1 -8 0.0202 0 -6 -3 0.0570 3 -5 -4 0.0524 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 H1 121.2(12) . . ? C1 N1 C2 111.08(12) . . ? C2 N1 H1 127.2(12) . . ? C1 N2 H2 124.2(12) . . ? C1 N2 C3 110.97(12) . . ? C3 N2 H2 124.7(12) . . ? C6 C5 C4 123.31(13) . . ? C6 C5 C10 119.01(14) . . ? C10 C5 C4 117.67(13) . . ? N1 C1 C4 123.44(13) . . ? N2 C1 N1 112.71(13) . . ? N2 C1 C4 123.85(13) . . ? N1 C2 H2A 111.3 . . ? N1 C2 H2B 111.3 . . ? N1 C2 C3 102.57(11) . . ? H2A C2 H2B 109.2 . . ? C3 C2 H2A 111.3 . . ? C3 C2 H2B 111.3 . . ? N2 C3 C2 102.58(11) . . ? N2 C3 H3A 111.3 . . ? N2 C3 H3B 111.3 . . ? C2 C3 H3A 111.3 . . ? C2 C3 H3B 111.3 . . ? H3A C3 H3B 109.2 . . ? C5 C6 H6 119.9 . . ? C5 C6 C7 120.29(14) . . ? C7 C6 H6 119.9 . . ? C5 C4 H4A 108.6 . . ? C5 C4 H4B 108.6 . . ? C1 C4 C5 114.72(12) . . ? C1 C4 H4A 108.6 . . ? C1 C4 H4B 108.6 . . ? H4A C4 H4B 107.6 . . ? C6 C7 H7 119.9 . . ? C8 C7 C6 120.18(15) . . ? C8 C7 H7 119.9 . . ? C5 C10 H10 119.7 . . ? C9 C10 C5 120.60(15) . . ? C9 C10 H10 119.7 . . ? C7 C8 H8 120.2 . . ? C9 C8 C7 119.60(15) . . ? C9 C8 H8 120.2 . . ? C10 C9 H9 119.8 . . ? C8 C9 C10 120.31(15) . . ? C8 C9 H9 119.8 . . ? 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 N1 H1 0.899(14) . ? N1 C1 1.3131(18) . ? N1 C2 1.4662(18) . ? N2 H2 0.905(14) . ? N2 C1 1.3109(18) . ? N2 C3 1.4689(18) . ? C5 C6 1.390(2) . ? C5 C4 1.518(2) . ? C5 C10 1.395(2) . ? C1 C4 1.4899(19) . ? C2 H2A 0.9900 . ? C2 H2B 0.9900 . ? C2 C3 1.5446(19) . ? C3 H3A 0.9900 . ? C3 H3B 0.9900 . ? C6 H6 0.9500 . ? C6 C7 1.396(2) . ? C4 H4A 0.9900 . ? C4 H4B 0.9900 . ? C7 H7 0.9500 . ? C7 C8 1.389(2) . ? C10 H10 0.9500 . ? C10 C9 1.386(2) . ? C8 H8 0.9500 . ? C8 C9 1.385(3) . ? C9 H9 0.9500 . ? 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 N1 C1 C4 C5 -88.49(17) . . . . ? N1 C2 C3 N2 -2.24(14) . . . . ? N2 C1 C4 C5 92.15(17) . . . . ? C5 C6 C7 C8 0.1(2) . . . . ? C5 C10 C9 C8 0.4(2) . . . . ? C1 N1 C2 C3 0.78(15) . . . . ? C1 N2 C3 C2 3.17(15) . . . . ? C2 N1 C1 N2 1.28(17) . . . . ? C2 N1 C1 C4 -178.14(12) . . . . ? C3 N2 C1 N1 -2.93(17) . . . . ? C3 N2 C1 C4 176.48(12) . . . . ? C6 C5 C4 C1 -1.7(2) . . . . ? C6 C5 C10 C9 -0.5(2) . . . . ? C6 C7 C8 C9 -0.2(2) . . . . ? C4 C5 C6 C7 -178.67(13) . . . . ? C4 C5 C10 C9 178.50(14) . . . . ? C7 C8 C9 C10 -0.1(2) . . . . ? C10 C5 C6 C7 0.3(2) . . . . ? C10 C5 C4 C1 179.38(13) . . . . ? 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 0.0002 0.0001 1.0000 0.0462 0.1206 -0.0029 -0.0002 -0.0001 -1.0000 -0.0462 -0.1206 0.0029 1.9998 2.0005 -0.9988 -0.2246 0.0249 -0.4231 -0.0004 -2.0004 1.0010 0.3399 0.0101 0.0862 -1.9991 1.0001 -0.0027 -0.2621 0.0201 0.2924 -1.9998 -2.0005 0.9988 0.2246 -0.0249 0.4231 1.9993 1.0001 -1.9983 -0.1240 -0.1509 -0.3757 -4.2286 0.4570 -3.8722 -0.4898 -0.5153 0.7033 1.1560 2.6784 -7.1520 -0.6572 -0.6942 -0.2936 -2.7632 -0.9770 -5.8037 -0.2842 -0.8019 0.5255 4.9544 1.4147 -5.0303 -0.1547 -0.4421 -0.8835 -4.9039 -1.5520 -1.9691 -0.1458 -0.4086 0.9010 0.0826 -2.6992 -6.9767 0.0784 -0.9889 0.1258 1.5533 -2.2500 -7.3781 0.0786 -0.9869 -0.1408 -1.9703 2.0852 7.3966 -0.0776 0.9728 0.2184 3.8728 -1.0556 -6.7711 0.0651 -0.8073 -0.5865 -0.0850 -4.3062 -5.4853 0.3735 -0.9008 0.2213 1.1332 4.3673 4.8609 -0.3510 0.8472 -0.3989 2.4802 -3.5070 -6.1770 0.3721 -0.8954 -0.2446 2.6858 5.3381 -2.0405 -0.7231 0.0957 -0.6841 -2.1998 1.6435 -6.1518 -0.6524 -0.6893 0.3151 2.1998 -1.6435 6.1518 0.6524 0.6893 -0.3151 3.3839 2.8243 -6.2011 -0.5062 -0.5327 -0.6782 0.3750 -0.7208 -7.7893 -0.2327 -0.9725 -0.0091 -0.2191 -5.6920 -2.8023 0.6933 -0.6562 0.2979 2.9362 -4.7782 -3.7264 0.6982 -0.6622 -0.2719