#------------------------------------------------------------------------------ #$Date: 2020-04-10 06:49:31 +0300 (Fri, 10 Apr 2020) $ #$Revision: 250583 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/15/74/7157462.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_7157462 loop_ _publ_author_name 'Fang, Benyao' 'Hou, Jiao' 'Tian, Jinyue' 'Yu, Wenquan' 'Chang, Junbiao' _publ_section_title ; Synthesis of Phenanthridines by I2-Mediated sp3 C−H Amination ; _journal_name_full 'Organic & Biomolecular Chemistry' _journal_paper_doi 10.1039/D0OB00433B _journal_year 2020 _chemical_formula_moiety 'C20 H14 Cl N' _chemical_formula_sum 'C20 H14 Cl N' _chemical_formula_weight 303.77 _chemical_melting_point 445.0(10) _chemical_name_systematic 2-chloro-6-(p-tolyl)phenanthridine _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary iterative _audit_creation_date 2019-10-10 _audit_creation_method ; Olex2 1.2 (compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) ; _audit_update_record ; 2020-01-28 deposited with the CCDC. 2020-04-09 downloaded from the CCDC. ; _cell_angle_alpha 105.531(8) _cell_angle_beta 91.027(9) _cell_angle_gamma 101.719(10) _cell_formula_units_Z 2 _cell_length_a 5.5878(7) _cell_length_b 10.8004(11) _cell_length_c 13.7039(12) _cell_measurement_reflns_used 1265 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 70.4740 _cell_measurement_theta_min 4.3670 _cell_volume 777.93(15) _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 (Dolomanov et al., 2009)' _computing_publication_material 'Olex2 (Dolomanov et al., 2009)' _computing_structure_refinement 'ShelXL (Sheldrick, 2015)' _computing_structure_solution ; Superflip (Palatinus & Chapuis, 2007;Palatinus & van der Lee, 2008; Palatinus et al., 2012) ; _diffrn_ambient_temperature 293(2) _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 16.2312 _diffrn_detector_type Eos _diffrn_measured_fraction_theta_full 0.998 _diffrn_measured_fraction_theta_max 0.998 _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 -62.00 36.00 1.00 1.00 -- -33.50 77.00 0.00 98 2 \w -36.00 74.00 1.00 1.00 -- 36.54 -19.00 -30.00 110 3 \w 29.00 102.00 1.00 1.00 -- 36.54-142.00 106.00 73 4 \w -4.00 77.00 1.00 1.00 -- 36.54 -99.00-120.00 81 5 \w -4.00 77.00 1.00 1.00 -- 36.54 -99.00 0.00 81 6 \w 18.00 105.00 1.00 1.00 -- 36.54 57.00-180.00 87 7 \w 57.00 111.00 1.00 1.00 -- 36.54 178.00-180.00 54 8 \w 8.00 106.00 1.00 1.00 -- 36.54 77.00 30.00 98 9 \w 8.00 106.00 1.00 1.00 -- 36.54 77.00 120.00 98 10 \w 18.00 105.00 1.00 1.00 -- 36.54 57.00 150.00 87 11 \w -31.00 31.00 1.00 1.00 -- 36.54 -57.00 -90.00 62 12 \w 61.00 86.00 1.00 1.00 -- 36.54 178.00 -30.00 25 13 \w 37.00 148.00 1.00 2.50 -- 108.00 -15.00 60.00 111 14 \w 37.00 129.00 1.00 2.50 -- 108.00 -30.00-120.00 92 15 \w 40.00 124.00 1.00 2.50 -- 108.00 -45.00 0.00 84 16 \w 38.00 99.00 1.00 2.50 -- 108.00 -94.00 150.00 61 17 \w 46.00 109.00 1.00 2.50 -- 108.00 -94.00 30.00 63 18 \w 111.00 138.00 1.00 2.50 -- 108.00 111.00-120.00 27 19 \w 40.00 108.00 1.00 2.50 -- 108.00 -77.00 -60.00 68 20 \w 79.00 110.00 1.00 2.50 -- 108.00 -94.00-180.00 31 21 \w 39.00 128.00 1.00 2.50 -- 108.00 -45.00 120.00 89 22 \w 89.00 116.00 1.00 2.50 -- 108.00 -77.00 30.00 27 23 \w 88.00 177.00 1.00 2.50 -- 108.00 30.00 60.00 89 24 \w 38.00 109.00 1.00 2.50 -- 108.00-111.00 -60.00 71 25 \w 80.00 107.00 1.00 2.50 -- 108.00 -15.00-180.00 27 ; _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'Xcalibur, Eos, Gemini' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_type 'CrysAlisPro convention (1999,Acta A55,543-557)' _diffrn_orient_matrix_UB_11 -0.1028395000 _diffrn_orient_matrix_UB_12 -0.1277592000 _diffrn_orient_matrix_UB_13 -0.0845308000 _diffrn_orient_matrix_UB_21 -0.0653036000 _diffrn_orient_matrix_UB_22 -0.0741416000 _diffrn_orient_matrix_UB_23 0.0808538000 _diffrn_orient_matrix_UB_31 -0.2547576000 _diffrn_orient_matrix_UB_32 0.0342929000 _diffrn_orient_matrix_UB_33 0.0034053000 _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54184 _diffrn_reflns_av_R_equivalents 0.0335 _diffrn_reflns_av_unetI/netI 0.0411 _diffrn_reflns_Laue_measured_fraction_full 0.998 _diffrn_reflns_Laue_measured_fraction_max 0.998 _diffrn_reflns_limit_h_max 4 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_k_min -10 _diffrn_reflns_limit_l_max 16 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_number 5607 _diffrn_reflns_point_group_measured_fraction_full 0.998 _diffrn_reflns_point_group_measured_fraction_max 0.998 _diffrn_reflns_theta_full 67.065 _diffrn_reflns_theta_max 67.065 _diffrn_reflns_theta_min 4.351 _diffrn_source 'fine-focus sealed X-ray tube' _diffrn_source_type 'Enhance (Cu) X-ray Source' _exptl_absorpt_coefficient_mu 2.113 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.83987 _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 colourless _exptl_crystal_colour_primary colourless _exptl_crystal_density_diffrn 1.297 _exptl_crystal_description prism _exptl_crystal_F_000 316 _exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: dichloromethane/hexane' _exptl_crystal_size_max 0.2 _exptl_crystal_size_mid 0.14 _exptl_crystal_size_min 0.1 _refine_diff_density_max 0.200 _refine_diff_density_min -0.205 _refine_diff_density_rms 0.044 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.015 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 200 _refine_ls_number_reflns 2778 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.015 _refine_ls_R_factor_all 0.0764 _refine_ls_R_factor_gt 0.0559 _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^)+(0.1092P)^2^+0.0003P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.1624 _refine_ls_wR_factor_ref 0.1918 _reflns_Friedel_coverage 0.000 _reflns_number_gt 1915 _reflns_number_total 2778 _reflns_threshold_expression 'I > 2\s(I)' _iucr_refine_instructions_details ; 201910251.res created by SHELXL-2014/7 TITL CF solution in P-1 CELL 1.54184 5.587772 10.80036 13.703858 105.5307 91.0266 101.7194 ZERR 2 0.000734 0.001069 0.00119 0.0081 0.0087 0.0097 LATT 1 SFAC C H Cl N UNIT 40 28 2 2 L.S. 4 0 0 PLAN 20 SIZE 0.1 0.14 0.2 MPLA C1 C2 C3 C4 C5 C6 C7 C8 C9 C10 C11 C12 C13 N1 MPLA C14 C15 C16 C17 C18 C19 bond $h conf fmap 2 acta REM REM REM WGHT 0.109200 0.000300 FVAR 9.25264 C1 1 0.331712 0.995887 0.331438 11.00000 0.10266 0.05844 = 0.05344 0.01754 0.01049 0.02380 AFIX 43 H1 2 0.246649 0.992201 0.388664 11.00000 -1.20000 AFIX 0 C2 1 0.558715 1.077083 0.340833 11.00000 0.10827 0.05432 = 0.05648 0.01081 -0.00972 0.01597 C3 1 0.691461 1.087735 0.258120 11.00000 0.08540 0.05157 = 0.07099 0.01599 -0.00885 0.01035 AFIX 43 H3 2 0.845481 1.143502 0.266855 11.00000 -1.20000 AFIX 0 C4 1 0.591875 1.014766 0.163439 11.00000 0.07147 0.05510 = 0.06354 0.01902 0.00305 0.01283 AFIX 43 H4 2 0.678798 1.021489 0.107168 11.00000 -1.20000 AFIX 0 C5 1 0.360557 0.929845 0.149736 11.00000 0.06787 0.04776 = 0.05604 0.01661 0.00353 0.01993 C6 1 0.228164 0.918122 0.234630 11.00000 0.07725 0.04882 = 0.05696 0.01924 0.00622 0.02486 C7 1 -0.005510 0.825484 0.216424 11.00000 0.07129 0.05317 = 0.06304 0.02391 0.01443 0.02604 C8 1 -0.092951 0.756673 0.115344 11.00000 0.06254 0.05021 = 0.06325 0.02287 0.01410 0.02289 C9 1 -0.318606 0.665829 0.095533 11.00000 0.06400 0.05942 = 0.07552 0.02563 0.01112 0.01624 AFIX 43 H9 2 -0.373912 0.620118 0.028648 11.00000 -1.20000 AFIX 0 C10 1 -0.459153 0.642828 0.172031 11.00000 0.07319 0.07173 = 0.09233 0.03441 0.02526 0.01831 AFIX 43 H10 2 -0.608602 0.582512 0.157812 11.00000 -1.20000 AFIX 0 C11 1 -0.373246 0.711924 0.271955 11.00000 0.09203 0.08183 = 0.09460 0.04508 0.04233 0.02761 AFIX 43 H11 2 -0.467854 0.697608 0.324641 11.00000 -1.20000 AFIX 0 C12 1 -0.153721 0.799974 0.294139 11.00000 0.09924 0.07110 = 0.06355 0.02643 0.02399 0.02876 AFIX 43 H12 2 -0.100805 0.843928 0.361567 11.00000 -1.20000 AFIX 0 C13 1 0.057364 0.781860 0.034831 11.00000 0.05618 0.04759 = 0.06011 0.01730 0.00972 0.01983 C14 1 -0.029908 0.717459 -0.073654 11.00000 0.05009 0.05072 = 0.05994 0.01782 0.00918 0.01155 C15 1 -0.229008 0.747151 -0.118259 11.00000 0.06267 0.06774 = 0.06782 0.01969 0.01124 0.02841 AFIX 43 H15 2 -0.317091 0.803737 -0.078612 11.00000 -1.20000 AFIX 0 C16 1 -0.296812 0.693713 -0.220297 11.00000 0.06095 0.07770 = 0.06774 0.02369 0.00039 0.02014 AFIX 43 H16 2 -0.428663 0.716184 -0.248597 11.00000 -1.20000 AFIX 0 C17 1 -0.174267 0.607702 -0.281659 11.00000 0.06213 0.06392 = 0.06093 0.01243 0.00552 -0.00119 C18 1 0.019569 0.575508 -0.237178 11.00000 0.06587 0.06644 = 0.06878 0.00390 0.01382 0.01828 AFIX 43 H18 2 0.102715 0.515999 -0.276576 11.00000 -1.20000 AFIX 0 C19 1 0.091731 0.630115 -0.135406 11.00000 0.05499 0.06475 = 0.07320 0.01424 0.00554 0.02362 AFIX 43 H19 2 0.224625 0.607946 -0.107600 11.00000 -1.20000 AFIX 0 C20 1 -0.249826 0.552689 -0.393888 11.00000 0.10812 0.09745 = 0.06146 0.00492 -0.00046 -0.00287 AFIX 137 H20A 2 -0.423500 0.517739 -0.403524 11.00000 -1.50000 H20B 2 -0.165451 0.483915 -0.422667 11.00000 -1.50000 H20C 2 -0.208542 0.621455 -0.426792 11.00000 -1.50000 AFIX 0 CL1 3 0.684763 1.171701 0.461989 11.00000 0.17798 0.09077 = 0.06567 0.00363 -0.02141 -0.00505 N1 4 0.272961 0.861665 0.050727 11.00000 0.06036 0.05605 = 0.05190 0.01608 0.00531 0.01467 HKLF 4 REM CF solution in P-1 REM R1 = 0.0559 for 1915 Fo > 4sig(Fo) and 0.0764 for all 2778 data REM 200 parameters refined using 0 restraints END WGHT 0.1091 0.0003 REM Highest difference peak 0.200, deepest hole -0.205, 1-sigma level 0.044 Q1 1 -0.0806 0.7912 0.0666 11.00000 0.05 0.17 Q2 1 -0.3031 0.4363 -0.4066 11.00000 0.05 0.17 Q3 1 1.0000 1.0000 0.0000 10.50000 0.05 0.17 Q4 1 0.6262 1.2248 0.4232 11.00000 0.05 0.16 Q5 1 -0.2060 0.6852 -0.0794 11.00000 0.05 0.15 Q6 1 0.7324 1.2807 0.4429 11.00000 0.05 0.15 Q7 1 -0.0448 0.7857 -0.1153 11.00000 0.05 0.14 Q8 1 0.2804 0.9192 -0.0024 11.00000 0.05 0.14 Q9 1 0.4109 0.9860 0.1752 11.00000 0.05 0.13 Q10 1 -0.0740 0.5484 -0.4445 11.00000 0.05 0.13 Q11 1 0.5892 1.0556 0.1005 11.00000 0.05 0.13 Q12 1 0.2390 0.9422 0.1812 11.00000 0.05 0.13 Q13 1 -0.2407 0.8974 -0.0843 11.00000 0.05 0.12 Q14 1 0.4979 1.0104 0.3418 11.00000 0.05 0.12 Q15 1 -0.2857 0.6341 0.1384 11.00000 0.05 0.12 Q16 1 -0.3214 0.3576 -0.4367 11.00000 0.05 0.12 Q17 1 -0.3843 0.6271 -0.0017 11.00000 0.05 0.12 Q18 1 0.3815 0.8414 -0.0695 11.00000 0.05 0.12 Q19 1 -0.2060 0.9046 0.3626 11.00000 0.05 0.12 Q20 1 0.3511 0.8809 0.2070 11.00000 0.05 0.12 REM The information below was added by Olex2. REM REM R1 = 0.0559 for 1915 Fo > 4sig(Fo) and 0.0764 for all 5607 data REM n/a parameters refined using n/a restraints REM Highest difference peak 0.20, deepest hole -0.20 REM Mean Shift 0, Max Shift 0.000. REM +++ Tabular Listing of Refinement Information +++ REM R1_all = 0.0764 REM R1_gt = 0.0559 REM wR_ref = 0.1918 REM GOOF = 1.015 REM Shift_max = 0.000 REM Shift_mean = 0 REM Reflections_all = 5607 REM Reflections_gt = 1915 REM Parameters = n/a REM Hole = -0.20 REM Peak = 0.20 REM Flack = n/a ; _cod_data_source_file d0ob00433b2.cif _cod_data_source_block 201910251 _cod_depositor_comments ; The following automatic conversions were performed: data item '_chemical_melting_point' value '444-446' was changed to '445.0(10)' -- the average value was taken and precision was estimated. Automatic conversion script Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas ; _cod_original_cell_volume 777.92(15) _cod_database_code 7157462 _shelx_shelxl_version_number 2014/7 _chemical_oxdiff_formula C20H20O4N1 _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 0.816 _shelx_estimated_absorpt_t_min 0.677 _reflns_odcompleteness_completeness 99.82 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 66.97 _olex2_refinement_description ; 1. Fixed Uiso At 1.2 times of: All C(H) groups At 1.5 times of: All C(H,H,H) groups 2.a Aromatic/amide H refined with riding coordinates: C1(H1), C3(H3), C4(H4), C9(H9), C10(H10), C11(H11), C12(H12), C15(H15), C16(H16), C18(H18), C19(H19) 2.b Idealised Me refined as rotating group: C20(H20A,H20B,H20C) ; _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 1.877 _oxdiff_exptl_absorpt_empirical_full_min 0.739 loop_ _space_group_symop_operation_xyz 'x, y, z' '-x, -y, -z' 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 C1 C 0.3317(5) 0.9959(2) 0.33144(18) 0.0701(7) Uani 1 1 d . . . . . H1 H 0.2466 0.9922 0.3887 0.084 Uiso 1 1 calc R . . . . C2 C 0.5587(6) 1.0771(2) 0.34083(19) 0.0744(7) Uani 1 1 d . . . . . C3 C 0.6915(5) 1.0877(2) 0.2581(2) 0.0704(7) Uani 1 1 d . . . . . H3 H 0.8455 1.1435 0.2669 0.084 Uiso 1 1 calc R . . . . C4 C 0.5919(4) 1.0148(2) 0.16344(18) 0.0630(6) Uani 1 1 d . . . . . H4 H 0.6788 1.0215 0.1072 0.076 Uiso 1 1 calc R . . . . C5 C 0.3606(4) 0.9298(2) 0.14974(17) 0.0557(6) Uani 1 1 d . . . . . C6 C 0.2282(4) 0.9181(2) 0.23463(17) 0.0584(6) Uani 1 1 d . . . . . C7 C -0.0055(4) 0.8255(2) 0.21642(18) 0.0590(6) Uani 1 1 d . . . . . C8 C -0.0930(4) 0.7567(2) 0.11534(17) 0.0556(6) Uani 1 1 d . . . . . C9 C -0.3186(4) 0.6658(2) 0.0955(2) 0.0644(6) Uani 1 1 d . . . . . H9 H -0.3739 0.6201 0.0286 0.077 Uiso 1 1 calc R . . . . C10 C -0.4592(5) 0.6428(3) 0.1720(2) 0.0761(8) Uani 1 1 d . . . . . H10 H -0.6086 0.5825 0.1578 0.091 Uiso 1 1 calc R . . . . C11 C -0.3732(6) 0.7119(3) 0.2720(2) 0.0837(9) Uani 1 1 d . . . . . H11 H -0.4679 0.6976 0.3246 0.100 Uiso 1 1 calc R . . . . C12 C -0.1537(5) 0.8000(3) 0.2941(2) 0.0747(7) Uani 1 1 d . . . . . H12 H -0.1008 0.8439 0.3616 0.090 Uiso 1 1 calc R . . . . C13 C 0.0574(4) 0.7819(2) 0.03483(17) 0.0528(5) Uani 1 1 d . . . . . C14 C -0.0299(4) 0.7175(2) -0.07365(17) 0.0529(5) Uani 1 1 d . . . . . C15 C -0.2290(4) 0.7472(2) -0.11826(19) 0.0637(6) Uani 1 1 d . . . . . H15 H -0.3171 0.8037 -0.0786 0.076 Uiso 1 1 calc R . . . . C16 C -0.2968(4) 0.6937(3) -0.22030(19) 0.0674(7) Uani 1 1 d . . . . . H16 H -0.4287 0.7162 -0.2486 0.081 Uiso 1 1 calc R . . . . C17 C -0.1743(4) 0.6077(2) -0.28166(18) 0.0655(6) Uani 1 1 d . . . . . C18 C 0.0196(5) 0.5755(3) -0.23718(19) 0.0693(7) Uani 1 1 d . . . . . H18 H 0.1027 0.5160 -0.2766 0.083 Uiso 1 1 calc R . . . . C19 C 0.0917(4) 0.6301(2) -0.13541(19) 0.0637(6) Uani 1 1 d . . . . . H19 H 0.2246 0.6079 -0.1076 0.076 Uiso 1 1 calc R . . . . C20 C -0.2498(6) 0.5527(3) -0.3939(2) 0.0962(10) Uani 1 1 d . . . . . H20A H -0.4235 0.5177 -0.4035 0.144 Uiso 1 1 calc GR . . . . H20B H -0.1655 0.4839 -0.4227 0.144 Uiso 1 1 calc GR . . . . H20C H -0.2085 0.6215 -0.4268 0.144 Uiso 1 1 calc GR . . . . Cl1 Cl 0.6848(2) 1.17170(9) 0.46199(6) 0.1204(5) Uani 1 1 d . . . . . N1 N 0.2730(3) 0.86166(18) 0.05073(13) 0.0556(5) Uani 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 C1 0.103(2) 0.0584(14) 0.0534(13) 0.0175(11) 0.0105(13) 0.0238(14) C2 0.108(2) 0.0543(13) 0.0565(14) 0.0108(11) -0.0097(14) 0.0160(14) C3 0.0854(17) 0.0516(13) 0.0710(16) 0.0160(12) -0.0088(13) 0.0104(12) C4 0.0715(15) 0.0551(13) 0.0635(14) 0.0190(11) 0.0031(11) 0.0128(11) C5 0.0679(14) 0.0478(11) 0.0560(12) 0.0166(10) 0.0035(10) 0.0199(10) C6 0.0773(15) 0.0488(11) 0.0570(13) 0.0192(10) 0.0062(11) 0.0249(11) C7 0.0713(15) 0.0532(12) 0.0630(13) 0.0239(11) 0.0144(11) 0.0260(11) C8 0.0625(13) 0.0502(12) 0.0632(13) 0.0229(10) 0.0141(10) 0.0229(10) C9 0.0640(14) 0.0594(13) 0.0755(15) 0.0256(12) 0.0111(12) 0.0162(11) C10 0.0732(17) 0.0717(16) 0.092(2) 0.0344(15) 0.0253(15) 0.0183(13) C11 0.092(2) 0.0818(18) 0.095(2) 0.0451(17) 0.0423(17) 0.0276(16) C12 0.099(2) 0.0711(16) 0.0636(15) 0.0264(13) 0.0240(14) 0.0288(15) C13 0.0562(12) 0.0476(11) 0.0601(13) 0.0173(10) 0.0097(10) 0.0198(10) C14 0.0501(12) 0.0507(11) 0.0599(12) 0.0178(10) 0.0092(9) 0.0115(9) C15 0.0627(14) 0.0677(14) 0.0678(14) 0.0197(12) 0.0112(11) 0.0284(12) C16 0.0610(14) 0.0777(16) 0.0677(15) 0.0237(13) 0.0004(11) 0.0201(12) C17 0.0621(14) 0.0639(14) 0.0609(14) 0.0124(11) 0.0055(11) -0.0012(11) C18 0.0659(15) 0.0664(15) 0.0688(16) 0.0039(12) 0.0138(12) 0.0183(12) C19 0.0550(13) 0.0648(14) 0.0732(15) 0.0142(12) 0.0055(11) 0.0236(11) C20 0.108(2) 0.097(2) 0.0615(16) 0.0049(15) -0.0005(15) -0.0029(18) Cl1 0.1780(11) 0.0908(6) 0.0657(5) 0.0036(4) -0.0214(5) -0.0050(6) N1 0.0604(11) 0.0561(10) 0.0519(10) 0.0161(8) 0.0053(8) 0.0147(9) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' 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_ _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 C2 C1 H1 120.2 . . ? C2 C1 C6 119.5(2) . . ? C6 C1 H1 120.2 . . ? C1 C2 C3 122.6(2) . . ? C1 C2 Cl1 118.7(2) . . ? C3 C2 Cl1 118.7(2) . . ? C2 C3 H3 120.7 . . ? C4 C3 C2 118.7(2) . . ? C4 C3 H3 120.7 . . ? C3 C4 H4 119.5 . . ? C3 C4 C5 121.0(2) . . ? C5 C4 H4 119.5 . . ? C4 C5 C6 119.9(2) . . ? N1 C5 C4 116.8(2) . . ? N1 C5 C6 123.3(2) . . ? C1 C6 C5 118.3(2) . . ? C1 C6 C7 124.1(2) . . ? C5 C6 C7 117.6(2) . . ? C8 C7 C6 118.6(2) . . ? C8 C7 C12 117.5(2) . . ? C12 C7 C6 123.9(2) . . ? C7 C8 C13 118.1(2) . . ? C9 C8 C7 119.8(2) . . ? C9 C8 C13 122.1(2) . . ? C8 C9 H9 119.2 . . ? C10 C9 C8 121.7(3) . . ? C10 C9 H9 119.2 . . ? C9 C10 H10 120.8 . . ? C9 C10 C11 118.5(3) . . ? C11 C10 H10 120.8 . . ? C10 C11 H11 119.2 . . ? C12 C11 C10 121.5(2) . . ? C12 C11 H11 119.2 . . ? C7 C12 H12 119.5 . . ? C11 C12 C7 121.1(3) . . ? C11 C12 H12 119.5 . . ? C8 C13 C14 120.8(2) . . ? N1 C13 C8 123.7(2) . . ? N1 C13 C14 115.50(19) . . ? C15 C14 C13 121.5(2) . . ? C19 C14 C13 121.0(2) . . ? C19 C14 C15 117.5(2) . . ? C14 C15 H15 119.6 . . ? C16 C15 C14 120.7(2) . . ? C16 C15 H15 119.6 . . ? C15 C16 H16 119.2 . . ? C15 C16 C17 121.7(2) . . ? C17 C16 H16 119.2 . . ? C16 C17 C18 117.8(2) . . ? C16 C17 C20 120.5(3) . . ? C18 C17 C20 121.8(3) . . ? C17 C18 H18 119.5 . . ? C19 C18 C17 121.1(2) . . ? C19 C18 H18 119.5 . . ? C14 C19 H19 119.4 . . ? C18 C19 C14 121.3(2) . . ? C18 C19 H19 119.4 . . ? C17 C20 H20A 109.5 . . ? C17 C20 H20B 109.5 . . ? C17 C20 H20C 109.5 . . ? H20A C20 H20B 109.5 . . ? H20A C20 H20C 109.5 . . ? H20B C20 H20C 109.5 . . ? C13 N1 C5 118.60(19) . . ? 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 C1 H1 0.9300 . ? C1 C2 1.370(4) . ? C1 C6 1.407(3) . ? C2 C3 1.383(4) . ? C2 Cl1 1.748(2) . ? C3 H3 0.9300 . ? C3 C4 1.365(3) . ? C4 H4 0.9300 . ? C4 C5 1.402(3) . ? C5 C6 1.410(3) . ? C5 N1 1.385(3) . ? C6 C7 1.446(3) . ? C7 C8 1.410(3) . ? C7 C12 1.411(3) . ? C8 C9 1.403(3) . ? C8 C13 1.448(3) . ? C9 H9 0.9300 . ? C9 C10 1.366(3) . ? C10 H10 0.9300 . ? C10 C11 1.395(4) . ? C11 H11 0.9300 . ? C11 C12 1.364(4) . ? C12 H12 0.9300 . ? C13 C14 1.488(3) . ? C13 N1 1.308(3) . ? C14 C15 1.393(3) . ? C14 C19 1.386(3) . ? C15 H15 0.9300 . ? C15 C16 1.375(3) . ? C16 H16 0.9300 . ? C16 C17 1.378(4) . ? C17 C18 1.381(4) . ? C17 C20 1.511(3) . ? C18 H18 0.9300 . ? C18 C19 1.378(3) . ? C19 H19 0.9300 . ? C20 H20A 0.9600 . ? C20 H20B 0.9600 . ? C20 H20C 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 C1 C2 C3 C4 0.2(4) . . . . ? C1 C6 C7 C8 177.8(2) . . . . ? C1 C6 C7 C12 -1.7(4) . . . . ? C2 C1 C6 C5 -1.9(4) . . . . ? C2 C1 C6 C7 177.5(2) . . . . ? C2 C3 C4 C5 -0.4(4) . . . . ? C3 C4 C5 C6 -0.5(4) . . . . ? C3 C4 C5 N1 178.9(2) . . . . ? C4 C5 C6 C1 1.7(3) . . . . ? C4 C5 C6 C7 -177.8(2) . . . . ? C4 C5 N1 C13 -179.73(19) . . . . ? C5 C6 C7 C8 -2.8(3) . . . . ? C5 C6 C7 C12 177.7(2) . . . . ? C6 C1 C2 C3 1.0(4) . . . . ? C6 C1 C2 Cl1 -179.45(18) . . . . ? C6 C5 N1 C13 -0.3(3) . . . . ? C6 C7 C8 C9 179.7(2) . . . . ? C6 C7 C8 C13 0.4(3) . . . . ? C6 C7 C12 C11 179.6(2) . . . . ? C7 C8 C9 C10 0.8(4) . . . . ? C7 C8 C13 C14 -176.96(18) . . . . ? C7 C8 C13 N1 2.2(3) . . . . ? C8 C7 C12 C11 0.0(4) . . . . ? C8 C9 C10 C11 -0.2(4) . . . . ? C8 C13 C14 C15 67.0(3) . . . . ? C8 C13 C14 C19 -116.1(2) . . . . ? C8 C13 N1 C5 -2.3(3) . . . . ? C9 C8 C13 C14 3.7(3) . . . . ? C9 C8 C13 N1 -177.1(2) . . . . ? C9 C10 C11 C12 -0.5(4) . . . . ? C10 C11 C12 C7 0.6(4) . . . . ? C12 C7 C8 C9 -0.7(3) . . . . ? C12 C7 C8 C13 -180.0(2) . . . . ? C13 C8 C9 C10 -180.0(2) . . . . ? C13 C14 C15 C16 175.4(2) . . . . ? C13 C14 C19 C18 -176.5(2) . . . . ? C14 C13 N1 C5 176.95(17) . . . . ? C14 C15 C16 C17 1.1(4) . . . . ? C15 C14 C19 C18 0.5(3) . . . . ? C15 C16 C17 C18 0.5(4) . . . . ? C15 C16 C17 C20 -178.8(2) . . . . ? C16 C17 C18 C19 -1.6(4) . . . . ? C17 C18 C19 C14 1.1(4) . . . . ? C19 C14 C15 C16 -1.6(3) . . . . ? C20 C17 C18 C19 177.7(2) . . . . ? Cl1 C2 C3 C4 -179.37(19) . . . . ? N1 C5 C6 C1 -177.7(2) . . . . ? N1 C5 C6 C7 2.9(3) . . . . ? N1 C13 C14 C15 -112.3(2) . . . . ? N1 C13 C14 C19 64.6(3) . . . . ?