#------------------------------------------------------------------------------ #$Date: 2024-04-11 02:40:52 +0300 (Thu, 11 Apr 2024) $ #$Revision: 291167 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/24/83/7248394.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_7248394 loop_ _publ_author_name 'Sch\"utte, Jonathan' 'Corsi, Daria' 'Haumer, Wolfgang' 'Schmid, Simon' 'Zurauskas, Jonas' 'Barham, Joshua Philip' _publ_section_title ; A Hydrazine Free Photoredox Catalytic Synthesis of Azines by Reductive Activation of Readily Available Oxime Esters ; _journal_name_full 'Green Chemistry' _journal_paper_doi 10.1039/D4GC00804A _journal_year 2024 _chemical_formula_moiety 'C16 H16 N2' _chemical_formula_sum 'C16 H16 N2' _chemical_formula_weight 236.31 _space_group_crystal_system monoclinic _space_group_IT_number 14 _space_group_name_Hall '-P 2yn' _space_group_name_H-M_alt 'P 1 21/n 1' _atom_sites_solution_hydrogens difmap _atom_sites_solution_primary dual _audit_creation_date 2023-05-10 _audit_creation_method ; Olex2 1.5-alpha (compiled 2022.06.10 svn.r3fa896fb for OlexSys, GUI svn.r6535) ; _audit_update_record ; 2023-08-13 deposited with the CCDC. 2024-04-03 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 97.5220(10) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 11.58810(10) _cell_length_b 7.38790(10) _cell_length_c 14.8464(2) _cell_measurement_reflns_used 11814 _cell_measurement_temperature 126.06(10) _cell_measurement_theta_max 73.9120 _cell_measurement_theta_min 3.8610 _cell_volume 1260.09(3) _computing_cell_refinement 'CrysAlisPro 1.171.42.73a (Rigaku OD, 2022)' _computing_data_collection 'CrysAlisPro 1.171.42.73a (Rigaku OD, 2022)' _computing_data_reduction 'CrysAlisPro 1.171.42.73a (Rigaku OD, 2022)' _computing_molecular_graphics 'Olex2 1.5-alpha (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 1.5-alpha (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 126.06(10) _diffrn_detector 'Hybrid Pixel Array Detector' _diffrn_detector_area_resol_mean 10.0000 _diffrn_detector_type 'HyPix-Arc 150' _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.968 _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 71.00 103.00 0.50 0.10 -- 76.31-125.00 60.00 64 2 \w 35.00 99.00 0.50 0.10 -- 71.85-125.00 90.00 128 3 \w 35.00 61.00 0.50 0.10 -- 76.31-125.00 60.00 52 4 \w 35.00 61.00 0.50 0.10 -- 76.31-125.00 120.00 52 5 \w 78.00 103.00 0.50 0.10 -- 76.31-125.00 120.00 50 6 \w 37.00 63.00 0.50 0.10 -- 76.31-125.00 30.00 52 7 \w 70.00 102.00 0.50 0.10 -- 76.31-125.00 30.00 64 8 \w 78.00 103.00 0.50 0.10 -- 76.31-125.00 -30.00 50 9 \w 45.00 71.00 0.50 0.10 -- 76.31-125.00 -30.00 52 10 \w 32.00 87.00 0.50 0.10 -- 71.85-105.00 -55.00 110 11 \w 66.00 91.00 0.50 0.10 -- 76.31-105.00 -55.00 50 12 \w 29.00 68.00 0.50 0.10 -- 64.17 -95.00 0.00 78 13 \w 27.00 56.00 0.50 0.10 -- 64.17 -95.00 30.00 58 14 \w 26.00 58.00 0.50 0.10 -- 64.17 -95.00 -30.00 64 15 \w 24.00 74.00 0.50 0.10 -- 64.17-105.00 -55.00 100 16 \w 39.00 74.00 0.50 0.10 -- 76.31 -95.00 120.00 70 17 \w 36.00 61.00 0.50 0.10 -- 71.85 -95.00 -60.00 50 18 \w 56.00 83.00 0.50 0.10 -- 76.31 -95.00-120.00 54 19 \w 27.00 53.00 0.50 0.10 -- 64.17 -95.00-180.00 52 20 \w 33.00 101.00 0.50 0.10 -- 64.17 0.00 -60.00 136 21 \w 72.00 97.00 0.50 0.10 -- 60.00 71.00 21.55 50 22 \w 66.00 91.00 0.50 0.10 -- 60.00 73.00 10.13 50 23 \w 59.00 84.00 0.50 0.10 -- 52.00 70.00 15.04 50 24 \w 53.00 78.00 0.50 0.10 -- 44.00 63.00 23.05 50 25 \w 41.00 66.00 0.50 0.10 -- 32.00 62.00 40.19 50 26 \w 67.00 92.00 0.50 0.10 -- 60.00 71.00 -7.34 50 27 \w 38.00 109.00 0.50 0.10 -- 71.85 0.00-120.00 142 28 \w 27.00 53.00 0.50 0.10 -- 64.17 0.00-120.00 52 29 \w 69.00 95.00 0.50 0.10 -- 64.17 0.00-120.00 52 30 \w 72.00 112.00 0.50 0.10 -- 76.31 15.00 -90.00 80 31 \w 41.00 66.00 0.50 0.10 -- 76.31 0.00 90.00 50 32 \w 74.00 99.00 0.50 0.10 -- 76.31 0.00 90.00 50 33 \w -63.00 -37.00 0.50 0.10 -- -76.25 140.00 27.65 52 34 \w -62.00 -35.00 0.50 0.10 -- -65.07 105.00 44.00 54 35 \w -86.00 -60.00 0.50 0.10 -- -71.26 105.00 44.00 52 36 \w -113.00 -88.00 0.50 0.10 -- -76.25 140.00 27.65 50 37 \w -82.00 -38.00 0.50 0.10 -- -71.26 0.00-120.00 88 38 \w -93.00 -34.00 0.50 0.10 -- -65.07 0.00-150.00 118 39 \w -102.00 -28.00 0.50 0.10 -- -65.07 0.00 -30.00 148 40 \w -98.00 -47.00 0.50 0.10 -- -65.07 0.00 90.00 102 41 \w -102.00 -72.00 0.50 0.10 -- -68.00 -76.00 -23.81 60 42 \w -102.00 -77.00 0.50 0.10 -- -72.00 -75.00 5.72 50 43 \w -105.00 -80.00 0.50 0.10 -- -72.00 -66.00 3.78 50 44 \w -105.00 -80.00 0.50 0.10 -- -72.00 -66.00 -20.23 50 45 \w -118.00 -93.00 0.50 0.10 -- -76.25 -61.00 -10.60 50 46 \w -109.00 -42.00 0.50 0.10 -- -71.26 -15.00-150.00 134 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'XtaLAB Synergy R, DW system, HyPix-Arc 150' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 0.0174900000 _diffrn_orient_matrix_UB_12 -0.2002943000 _diffrn_orient_matrix_UB_13 -0.0236838000 _diffrn_orient_matrix_UB_21 -0.0929485000 _diffrn_orient_matrix_UB_22 0.0184565000 _diffrn_orient_matrix_UB_23 -0.0837391000 _diffrn_orient_matrix_UB_31 0.0950612000 _diffrn_orient_matrix_UB_32 0.0549512000 _diffrn_orient_matrix_UB_33 -0.0581701000 _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 0.0159 _diffrn_reflns_av_unetI/netI 0.0087 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.968 _diffrn_reflns_limit_h_max 14 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_k_max 9 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_number 16836 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.968 _diffrn_reflns_theta_full 67.684 _diffrn_reflns_theta_max 73.812 _diffrn_reflns_theta_min 4.562 _diffrn_source 'Rotating-anode X-ray tube' _diffrn_source_type 'Rigaku (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 0.570 _exptl_absorpt_correction_T_max 1.000 _exptl_absorpt_correction_T_min 0.462 _exptl_absorpt_correction_type gaussian _exptl_absorpt_process_details ; CrysAlisPro 1.171.42.73a (Rigaku Oxford Diffraction, 2022) 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 colourless' _exptl_crystal_colour_lustre clear _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.246 _exptl_crystal_description prism _exptl_crystal_F_000 504 _exptl_crystal_size_max 0.263 _exptl_crystal_size_mid 0.197 _exptl_crystal_size_min 0.075 _refine_diff_density_max 0.203 _refine_diff_density_min -0.187 _refine_diff_density_rms 0.037 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.080 _refine_ls_hydrogen_treatment refall _refine_ls_matrix_type full _refine_ls_number_parameters 227 _refine_ls_number_reflns 2468 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.080 _refine_ls_R_factor_all 0.0335 _refine_ls_R_factor_gt 0.0324 _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^)+(0.0538P)^2^+0.2444P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0928 _refine_ls_wR_factor_ref 0.0938 _reflns_Friedel_coverage 0.000 _reflns_number_gt 2351 _reflns_number_total 2468 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file d4gc00804a2.cif _cod_data_source_block w037 _cod_database_code 7248394 _shelx_shelxl_version_number 2018/3 _chemical_oxdiff_formula 'C16 H16 N2' _chemical_oxdiff_usercomment Corsi_Barham_JS-Model_product _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 0.959 _shelx_estimated_absorpt_t_min 0.865 _olex2_refinement_description ; ; _shelx_res_file ; TITL w037_a.res in P2(1)/n w037.res created by SHELXL-2018/3 at 08:42:25 on 10-May-2023 REM Old TITL W037 in P2(1)/n REM SHELXT solution in P2(1)/n: R1 0.115, Rweak 0.004, Alpha 0.018 REM 0.791 for 206 systematic absences, Orientation as input REM Formula found by SHELXT: C16 N2 CELL 1.54184 11.5881 7.3879 14.8464 90 97.522 90 ZERR 4 0.0001 0.0001 0.0002 0 0.001 0 LATT 1 SYMM 0.5-X,0.5+Y,0.5-Z SFAC C H N UNIT 64 64 8 L.S. 4 0 0 PLAN 1 SIZE 0.075 0.197 0.263 TEMP -147 CONF BOND list 4 fmap 2 53 ACTA MORE -1 BOND $H REM REM REM WGHT 0.053800 0.244400 FVAR 0.68601 N1 3 0.633792 0.200163 0.488928 11.00000 0.02176 0.02208 = 0.01651 0.00045 0.00233 -0.00045 N2 3 0.595267 0.201824 0.395835 11.00000 0.02171 0.02392 = 0.01651 0.00017 0.00247 -0.00039 C7 1 0.553104 0.225461 0.539670 11.00000 0.01949 0.01371 = 0.02005 0.00082 0.00302 -0.00149 C15 1 0.662317 0.283235 0.346410 11.00000 0.01795 0.01595 = 0.01976 -0.00032 0.00305 0.00299 C14 1 0.685653 0.377713 0.186931 11.00000 0.01975 0.01880 = 0.02312 0.00069 0.00476 0.00111 C9 1 0.623394 0.283821 0.246730 11.00000 0.01859 0.01587 = 0.01966 0.00000 0.00409 0.00334 C1 1 0.589002 0.219778 0.639373 11.00000 0.01878 0.01492 = 0.01897 0.00077 0.00380 -0.00221 C13 1 0.646164 0.382830 0.094213 11.00000 0.02471 0.02204 = 0.02186 0.00366 0.00878 0.00419 C5 1 0.556654 0.301040 0.792110 11.00000 0.02275 0.02305 = 0.02154 -0.00230 0.00779 -0.00123 C6 1 0.520485 0.299960 0.699074 11.00000 0.01879 0.02024 = 0.02287 0.00082 0.00405 0.00116 C10 1 0.520820 0.193932 0.211281 11.00000 0.02079 0.02318 = 0.02044 0.00225 0.00391 -0.00112 C2 1 0.694130 0.138573 0.675513 11.00000 0.02072 0.02039 = 0.02087 -0.00017 0.00508 0.00231 C8 1 0.428199 0.264722 0.503722 11.00000 0.01877 0.02808 = 0.02165 0.00118 0.00148 0.00010 C4 1 0.660420 0.218252 0.827118 11.00000 0.02507 0.02270 = 0.01781 0.00059 0.00245 -0.00329 C3 1 0.728793 0.136523 0.768405 11.00000 0.02081 0.02434 = 0.02309 0.00177 0.00123 0.00227 C16 1 0.772901 0.378966 0.382716 11.00000 0.02176 0.03066 = 0.02061 0.00187 0.00041 -0.00443 C12 1 0.544781 0.292847 0.060088 11.00000 0.02756 0.02708 = 0.01669 0.00153 0.00214 0.00527 C11 1 0.482635 0.198022 0.118913 11.00000 0.02308 0.02841 = 0.02197 0.00008 0.00019 -0.00159 H2 2 0.742468 0.081718 0.634730 11.00000 0.02575 H6 2 0.448424 0.360680 0.674872 11.00000 0.02563 H14 2 0.756331 0.443513 0.209845 11.00000 0.02649 H13 2 0.689054 0.450576 0.052811 11.00000 0.02724 H12 2 0.516850 0.295013 -0.004651 11.00000 0.02978 H10 2 0.478369 0.127286 0.251467 11.00000 0.02562 H4 2 0.684208 0.217112 0.893561 11.00000 0.02415 H3 2 0.801482 0.077958 0.792200 11.00000 0.02901 H5 2 0.509298 0.362077 0.833573 11.00000 0.02703 H11 2 0.410637 0.134856 0.096067 11.00000 0.03283 H8A 2 0.374056 0.210022 0.542753 11.00000 0.03514 H16A 2 0.764390 0.511251 0.375713 11.00000 0.04270 H8B 2 0.412212 0.395304 0.502049 11.00000 0.03787 H8C 2 0.409850 0.218766 0.441018 11.00000 0.04014 H16B 2 0.837306 0.343750 0.349035 11.00000 0.04023 H16C 2 0.795849 0.348817 0.446235 11.00000 0.04692 HKLF 4 REM w037_a.res in P2(1)/n REM wR2 = 0.0938, GooF = S = 1.080, Restrained GooF = 1.080 for all data REM R1 = 0.0324 for 2351 Fo > 4sig(Fo) and 0.0335 for all 2468 data REM 227 parameters refined using 0 restraints END WGHT 0.0538 0.2444 REM Highest difference peak 0.203, deepest hole -0.187, 1-sigma level 0.037 Q1 1 0.4907 0.2445 0.5239 11.00000 0.05 0.20 ; _shelx_res_checksum 2083 _olex2_date_sample_data_collection 2023-05-08 _olex2_date_sample_submission 2023-04-28 _olex2_diffrn_ambient_temperature_device 'Oxford Cryosystems Cryostream 700' _olex2_exptl_crystal_mounting_method 'The crystal was mounted on a MITIGEN holder inert oil' _olex2_submission_original_sample_id JS-Model-product _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 - B-factor correction ; _oxdiff_exptl_absorpt_empirical_full_max 1.368 _oxdiff_exptl_absorpt_empirical_full_min 0.831 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x+1/2, y+1/2, -z+1/2' '-x, -y, -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 N1 N 0.63379(6) 0.20016(10) 0.48893(5) 0.02013(19) Uani 1 1 d . . . . . N2 N 0.59527(6) 0.20182(10) 0.39584(5) 0.02072(19) Uani 1 1 d . . . . . C7 C 0.55310(7) 0.22546(11) 0.53967(6) 0.0177(2) Uani 1 1 d . . . . . C15 C 0.66232(7) 0.28324(11) 0.34641(6) 0.0178(2) Uani 1 1 d . . . . . C14 C 0.68565(7) 0.37771(12) 0.18693(6) 0.0204(2) Uani 1 1 d . . . . . C9 C 0.62339(7) 0.28382(11) 0.24673(6) 0.0179(2) Uani 1 1 d . . . . . C1 C 0.58900(7) 0.21978(11) 0.63937(6) 0.0174(2) Uani 1 1 d . . . . . C13 C 0.64616(8) 0.38283(12) 0.09421(6) 0.0224(2) Uani 1 1 d . . . . . C5 C 0.55665(8) 0.30104(12) 0.79211(6) 0.0220(2) Uani 1 1 d . . . . . C6 C 0.52048(8) 0.29996(12) 0.69907(6) 0.0205(2) Uani 1 1 d . . . . . C10 C 0.52082(8) 0.19393(12) 0.21128(6) 0.0214(2) Uani 1 1 d . . . . . C2 C 0.69413(7) 0.13857(12) 0.67551(6) 0.0204(2) Uani 1 1 d . . . . . C8 C 0.42820(8) 0.26472(13) 0.50372(6) 0.0229(2) Uani 1 1 d . . . . . C4 C 0.66042(8) 0.21825(12) 0.82712(6) 0.0219(2) Uani 1 1 d . . . . . C3 C 0.72879(8) 0.13652(13) 0.76840(6) 0.0229(2) Uani 1 1 d . . . . . C16 C 0.77290(8) 0.37897(13) 0.38272(6) 0.0246(2) Uani 1 1 d . . . . . C12 C 0.54478(8) 0.29285(13) 0.06009(6) 0.0238(2) Uani 1 1 d . . . . . C11 C 0.48263(8) 0.19802(13) 0.11891(6) 0.0247(2) Uani 1 1 d . . . . . H2 H 0.7425(9) 0.0817(16) 0.6347(7) 0.026(3) Uiso 1 1 d . . . . . H6 H 0.4484(10) 0.3607(16) 0.6749(7) 0.026(3) Uiso 1 1 d . . . . . H14 H 0.7563(10) 0.4435(17) 0.2098(7) 0.026(3) Uiso 1 1 d . . . . . H13 H 0.6891(9) 0.4506(16) 0.0528(7) 0.027(3) Uiso 1 1 d . . . . . H12 H 0.5168(10) 0.2950(16) -0.0047(8) 0.030(3) Uiso 1 1 d . . . . . H10 H 0.4784(9) 0.1273(16) 0.2515(8) 0.026(3) Uiso 1 1 d . . . . . H4 H 0.6842(9) 0.2171(15) 0.8936(8) 0.024(3) Uiso 1 1 d . . . . . H3 H 0.8015(10) 0.0780(16) 0.7922(8) 0.029(3) Uiso 1 1 d . . . . . H5 H 0.5093(10) 0.3621(16) 0.8336(8) 0.027(3) Uiso 1 1 d . . . . . H11 H 0.4106(10) 0.1349(17) 0.0961(8) 0.033(3) Uiso 1 1 d . . . . . H8A H 0.3741(11) 0.2100(17) 0.5428(8) 0.035(3) Uiso 1 1 d . . . . . H16A H 0.7644(11) 0.5113(19) 0.3757(8) 0.043(3) Uiso 1 1 d . . . . . H8B H 0.4122(10) 0.3953(19) 0.5020(8) 0.038(3) Uiso 1 1 d . . . . . H8C H 0.4099(11) 0.2188(18) 0.4410(9) 0.040(3) Uiso 1 1 d . . . . . H16B H 0.8373(11) 0.3437(19) 0.3490(9) 0.040(3) Uiso 1 1 d . . . . . H16C H 0.7958(11) 0.349(2) 0.4462(9) 0.047(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 N1 0.0218(4) 0.0221(4) 0.0165(4) 0.0004(3) 0.0023(3) -0.0005(3) N2 0.0217(4) 0.0239(4) 0.0165(4) 0.0002(3) 0.0025(3) -0.0004(3) C7 0.0195(4) 0.0137(4) 0.0200(4) 0.0008(3) 0.0030(3) -0.0015(3) C15 0.0179(4) 0.0159(4) 0.0198(4) -0.0003(3) 0.0030(3) 0.0030(3) C14 0.0197(4) 0.0188(4) 0.0231(4) 0.0007(3) 0.0048(3) 0.0011(3) C9 0.0186(4) 0.0159(4) 0.0197(4) 0.0000(3) 0.0041(3) 0.0033(3) C1 0.0188(4) 0.0149(4) 0.0190(4) 0.0008(3) 0.0038(3) -0.0022(3) C13 0.0247(4) 0.0220(4) 0.0219(4) 0.0037(3) 0.0088(3) 0.0042(3) C5 0.0227(4) 0.0230(5) 0.0215(4) -0.0023(3) 0.0078(3) -0.0012(3) C6 0.0188(4) 0.0202(4) 0.0229(4) 0.0008(3) 0.0041(3) 0.0012(3) C10 0.0208(4) 0.0232(5) 0.0204(4) 0.0023(3) 0.0039(3) -0.0011(3) C2 0.0207(4) 0.0204(4) 0.0209(4) -0.0002(3) 0.0051(3) 0.0023(3) C8 0.0188(4) 0.0281(5) 0.0217(4) 0.0012(4) 0.0015(3) 0.0001(3) C4 0.0251(4) 0.0227(5) 0.0178(4) 0.0006(3) 0.0024(3) -0.0033(3) C3 0.0208(4) 0.0243(5) 0.0231(4) 0.0018(3) 0.0012(3) 0.0023(3) C16 0.0218(4) 0.0307(5) 0.0206(4) 0.0019(4) 0.0004(3) -0.0044(4) C12 0.0276(5) 0.0271(5) 0.0167(4) 0.0015(3) 0.0021(3) 0.0053(3) C11 0.0231(4) 0.0284(5) 0.0220(5) 0.0001(4) 0.0002(4) -0.0016(4) 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' loop_ _exptl_crystal_face_index_h _exptl_crystal_face_index_k _exptl_crystal_face_index_l _exptl_crystal_face_perp_dist 5 0 7 0.0286 -5 0 -7 0.0459 7 1 -3 0.0935 7 1 -5 0.1042 5 2 -8 0.1205 2 -5 -1 0.0941 0 -5 3 0.0842 6 1 -6 0.1086 0 -5 3 0.0858 -6 -1 6 0.1315 -3 4 1 0.0831 0 3 7 0.0512 4 -3 5 0.0657 3 -3 6 0.0677 6 -1 5 0.0544 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 C7 N1 N2 114.52(7) . . ? C15 N2 N1 115.49(7) . . ? N1 C7 C1 116.65(7) . . ? N1 C7 C8 123.97(8) . . ? C1 C7 C8 119.36(7) . . ? N2 C15 C9 116.19(8) . . ? N2 C15 C16 124.53(8) . . ? C9 C15 C16 119.26(7) . . ? C9 C14 H14 120.4(6) . . ? C13 C14 C9 120.70(8) . . ? C13 C14 H14 118.9(6) . . ? C14 C9 C15 121.17(8) . . ? C14 C9 C10 118.60(8) . . ? C10 C9 C15 120.20(8) . . ? C6 C1 C7 120.81(8) . . ? C6 C1 C2 118.48(8) . . ? C2 C1 C7 120.68(8) . . ? C14 C13 H13 120.5(6) . . ? C12 C13 C14 120.06(8) . . ? C12 C13 H13 119.5(6) . . ? C6 C5 H5 120.2(7) . . ? C4 C5 C6 120.22(8) . . ? C4 C5 H5 119.6(7) . . ? C1 C6 H6 119.5(6) . . ? C5 C6 C1 120.70(8) . . ? C5 C6 H6 119.8(6) . . ? C9 C10 H10 119.3(7) . . ? C11 C10 C9 120.43(8) . . ? C11 C10 H10 120.3(7) . . ? C1 C2 H2 119.3(6) . . ? C3 C2 C1 120.70(8) . . ? C3 C2 H2 120.0(6) . . ? C7 C8 H8A 111.5(7) . . ? C7 C8 H8B 111.6(7) . . ? C7 C8 H8C 110.3(8) . . ? H8A C8 H8B 106.4(10) . . ? H8A C8 H8C 109.6(10) . . ? H8B C8 H8C 107.3(10) . . ? C5 C4 C3 119.57(8) . . ? C5 C4 H4 119.5(6) . . ? C3 C4 H4 121.0(6) . . ? C2 C3 C4 120.31(8) . . ? C2 C3 H3 119.4(7) . . ? C4 C3 H3 120.2(7) . . ? C15 C16 H16A 111.1(8) . . ? C15 C16 H16B 111.2(8) . . ? C15 C16 H16C 110.7(8) . . ? H16A C16 H16B 106.2(11) . . ? H16A C16 H16C 109.9(11) . . ? H16B C16 H16C 107.6(11) . . ? C13 C12 C11 119.69(8) . . ? C13 C12 H12 120.6(7) . . ? C11 C12 H12 119.7(7) . . ? C10 C11 C12 120.52(9) . . ? C10 C11 H11 118.7(7) . . ? C12 C11 H11 120.7(7) . . ? 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 N2 1.3957(10) . ? N1 C7 1.2888(11) . ? N2 C15 1.2858(11) . ? C7 C1 1.4848(11) . ? C7 C8 1.5039(12) . ? C15 C9 1.4896(12) . ? C15 C16 1.5007(12) . ? C14 C9 1.3991(12) . ? C14 C13 1.3931(12) . ? C14 H14 0.975(12) . ? C9 C10 1.4025(12) . ? C1 C6 1.3969(12) . ? C1 C2 1.4003(12) . ? C13 C12 1.3867(13) . ? C13 H13 0.977(12) . ? C5 C6 1.3900(12) . ? C5 C4 1.3880(13) . ? C5 H5 0.986(12) . ? C6 H6 0.974(11) . ? C10 C11 1.3851(12) . ? C10 H10 0.958(11) . ? C2 C3 1.3851(12) . ? C2 H2 0.972(11) . ? C8 H8A 0.994(12) . ? C8 H8B 0.982(14) . ? C8 H8C 0.988(13) . ? C4 C3 1.3903(13) . ? C4 H4 0.989(11) . ? C3 H3 0.971(12) . ? C16 H16A 0.986(14) . ? C16 H16B 0.986(13) . ? C16 H16C 0.972(14) . ? C12 C11 1.3917(13) . ? C12 H12 0.973(12) . ? C11 H11 0.977(12) . ? 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 N2 C15 C9 179.09(7) . . . . ? N1 N2 C15 C16 -2.48(12) . . . . ? N1 C7 C1 C6 159.45(8) . . . . ? N1 C7 C1 C2 -18.62(11) . . . . ? N2 N1 C7 C1 178.34(7) . . . . ? N2 N1 C7 C8 -3.44(12) . . . . ? N2 C15 C9 C14 176.04(8) . . . . ? N2 C15 C9 C10 -2.01(12) . . . . ? C7 N1 N2 C15 139.66(8) . . . . ? C7 C1 C6 C5 -177.30(7) . . . . ? C7 C1 C2 C3 178.66(8) . . . . ? C15 C9 C10 C11 178.31(8) . . . . ? C14 C9 C10 C11 0.22(13) . . . . ? C14 C13 C12 C11 0.19(13) . . . . ? C9 C14 C13 C12 -0.64(13) . . . . ? C9 C10 C11 C12 -0.66(14) . . . . ? C1 C2 C3 C4 -1.17(13) . . . . ? C13 C14 C9 C15 -177.65(7) . . . . ? C13 C14 C9 C10 0.43(12) . . . . ? C13 C12 C11 C10 0.46(14) . . . . ? C5 C4 C3 C2 0.42(13) . . . . ? C6 C1 C2 C3 0.55(12) . . . . ? C6 C5 C4 C3 0.93(13) . . . . ? C2 C1 C6 C5 0.81(12) . . . . ? C8 C7 C1 C6 -18.86(11) . . . . ? C8 C7 C1 C2 163.07(8) . . . . ? C4 C5 C6 C1 -1.56(13) . . . . ? C16 C15 C9 C14 -2.48(12) . . . . ? C16 C15 C9 C10 179.47(8) . . . . ? 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 4.7067 0.2683 6.6426 -0.1287 -0.9888 0.0758 -4.7240 -0.2722 -6.6215 0.1287 0.9885 -0.0788 7.1667 1.2370 -2.7337 -0.0577 -0.4144 0.9083 6.6106 0.9810 -5.2276 0.0429 -0.1586 0.9864 4.5667 1.6763 -7.5839 -0.0763 0.2415 0.9674 2.0293 -4.6175 -0.5056 0.9723 -0.2315 -0.0314 -0.0604 -4.6043 2.6829 0.8576 -0.3040 -0.4148 6.1038 0.8976 -6.3136 0.0765 -0.0221 0.9968 -0.3222 -4.5715 2.9131 0.8410 -0.2984 -0.4513 -6.2477 -0.5529 6.2538 -0.1466 0.0468 -0.9881 -3.1706 4.3494 0.5334 -0.9392 0.3303 -0.0934 0.4690 3.2704 6.8828 -0.8098 -0.5596 -0.1761 3.9915 -2.9956 5.0041 0.5513 -0.8453 -0.0763 2.9912 -2.9954 6.0050 0.5100 -0.8362 -0.2296 5.9882 -0.9955 5.0038 0.1856 -0.9940 0.2235