#------------------------------------------------------------------------------ #$Date: 2016-02-13 14:50:18 +0200 (Sat, 13 Feb 2016) $ #$Revision: 176428 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/22/23/7222300.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_7222300 loop_ _publ_author_name 'Camus, Nathalie' 'Halme, Zakaria' 'Nathalie, Le Bris' 'Bernard, H\'el\`ene' 'Beyler, Maryline' 'Platas-Iglesias, Carlos' 'Tripier, Raphael' _publ_section_title ; A [Two-Steps / One Week] Synthesis of C-Functionalized Homocyclens and Cyclams. Application to the Preparation of Conjugable BCAs without Chelating Properties Alteration ; _journal_name_full 'RSC Adv.' _journal_paper_doi 10.1039/C5RA17133D _journal_year 2015 _chemical_absolute_configuration ad _chemical_formula_moiety 'C16 H27 Cl N4 O' _chemical_formula_sum 'C16 H27 Cl N4 O' _chemical_formula_weight 326.87 _chemical_name_systematic ; ? ; _space_group_IT_number 33 _symmetry_cell_setting orthorhombic _symmetry_Int_Tables_number 33 _symmetry_space_group_name_Hall 'P 2c -2n' _symmetry_space_group_name_H-M 'P n a 21' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _audit_creation_date 2013-12-04T10:36:37-00:00 _audit_creation_method 'WinGX routine CIF_UPDATE' _audit_update_record ; 2015-07-13 deposited with the CCDC. 2015-09-25 downloaded from the CCDC. ; _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 19.2249(8) _cell_length_b 13.6646(5) _cell_length_c 6.0897(2) _cell_measurement_reflns_used 6056 _cell_measurement_temperature 297(2) _cell_measurement_theta_max 31.5471 _cell_measurement_theta_min 2.9758 _cell_volume 1599.77(10) _computing_cell_refinement ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET) (compiled Nov 6 2009,16:24:50) ; _computing_data_collection ; CrysAlis CCD, Oxford Diffraction Ltd., Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET) (compiled Nov 6 2009,16:24:50) ; _computing_data_reduction ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET) (compiled Nov 6 2009,16:24:50) ; _computing_molecular_graphics 'ORTEP3 for Windows (Farrugia, 1997)' _computing_publication_material ; WinGX (Farrugia, 1999) PLATON (Spek, 1990-2003) enCIFer (Allen et al., 2004) ; _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_structure_solution 'SIR-92 (Altomare et al., 1992)' _diffrn_ambient_temperature 297(2) _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 8.3622 _diffrn_measured_fraction_theta_full 0.997 _diffrn_measured_fraction_theta_max 0.997 _diffrn_measurement_device 'Kappa-geometry diffractometer' _diffrn_measurement_device_type 'Xcalibur, Sapphire2, large Be window' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 -0.0121135237 _diffrn_orient_matrix_UB_12 0.0496949198 _diffrn_orient_matrix_UB_13 0.0098804826 _diffrn_orient_matrix_UB_21 -0.0195191862 _diffrn_orient_matrix_UB_22 -0.0146610448 _diffrn_orient_matrix_UB_23 0.0348209865 _diffrn_orient_matrix_UB_31 0.1141174191 _diffrn_orient_matrix_UB_32 0.0027467641 _diffrn_orient_matrix_UB_33 0.0070104055 _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0282 _diffrn_reflns_av_unetI/netI 0.0256 _diffrn_reflns_limit_h_max 25 _diffrn_reflns_limit_h_min -25 _diffrn_reflns_limit_k_max 18 _diffrn_reflns_limit_k_min -18 _diffrn_reflns_limit_l_max 8 _diffrn_reflns_limit_l_min -5 _diffrn_reflns_number 13686 _diffrn_reflns_theta_full 28.27 _diffrn_reflns_theta_max 28.27 _diffrn_reflns_theta_min 3.16 _diffrn_source 'sealed X-ray tube' _exptl_absorpt_coefficient_mu 0.247 _exptl_absorpt_correction_T_max 0.9829 _exptl_absorpt_correction_T_min 0.9404 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlis RED, Oxford Diffraction Ltd., Version 1.171.33.52 (release 06-11-2009 CrysAlis171 .NET) (compiled Nov 6 2009,16:24:50) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.357 _exptl_crystal_density_method 'not measured' _exptl_crystal_description 'planar // (1 0 0)' _exptl_crystal_F_000 704 _exptl_crystal_recrystallization_method ; from hexane solution, by slow evaporation of solvent at room temperature ; _exptl_crystal_size_max 0.35 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_min 0.07 _refine_diff_density_max 0.314 _refine_diff_density_min -0.136 _refine_diff_density_rms 0.054 _refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881' _refine_ls_abs_structure_Flack -0.02(8) _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.01 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 201 _refine_ls_number_reflns 2980 _refine_ls_number_restraints 1 _refine_ls_restrained_S_all 1.009 _refine_ls_R_factor_all 0.0533 _refine_ls_R_factor_gt 0.0428 _refine_ls_shift/su_max 0 _refine_ls_shift/su_mean 0 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0656P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0984 _refine_ls_wR_factor_ref 0.102 _reflns_number_gt 2434 _reflns_number_total 2980 _reflns_threshold_expression >2sigma(I) _cod_data_source_file c5ra17133d2.cif _cod_data_source_block nc526-a _cod_depositor_comments ; The following automatic conversions were performed: '_diffrn_radiation_probe' value 'X-ray' changed to 'x-ray' according to /usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26. Automatic conversion script Id: cif_fix_values 3271 2015-04-21 07:52:19Z andrius ; _cod_original_sg_symbol_Hall P2c-2n _cod_original_sg_symbol_H-M Pna21 _cod_database_code 7222300 #BEGIN Tags that were not found in dictionaries: _iucr_refine_instruction_details ; TITL NC526-a at 297 K in Pna2(1) (#33 in standard setting) CELL 0.71073 19.2249 13.6646 6.0897 90.000 90.000 90.000 ZERR 4.00 0.0008 0.0005 0.0002 0.000 0.000 0.000 LATT -1 SYMM - X, - Y, 1/2 + Z SYMM 1/2 - X, 1/2 + Y, 1/2 + Z SYMM 1/2 + X, 1/2 - Y, Z SFAC C H N O CL UNIT 64 108 16 4 4 MERG 2 OMIT 0 2 0 SHEL 13 0.75 FMAP 2 PLAN 25 SIZE 0.07 0.28 0.35 ACTA BOND $H L.S. 4 TEMP 24.00 WGHT 0.065600 FVAR 1.20971 MOLE 1 C1 1 0.250844 0.280113 0.188524 11.00000 0.04634 0.02507 = 0.04006 -0.00229 -0.00063 -0.00311 AFIX 23 H1A 2 0.259774 0.210391 0.178444 11.00000 -1.20000 H1B 2 0.267667 0.310616 0.054859 11.00000 -1.20000 AFIX 0 C2 1 0.174165 0.297277 0.209801 11.00000 0.04438 0.03012 = 0.04045 -0.00527 -0.00232 -0.00817 AFIX 23 H2A 2 0.150460 0.272357 0.080787 11.00000 -1.20000 H2B 2 0.156503 0.262670 0.337208 11.00000 -1.20000 AFIX 0 C3 1 0.085037 0.419466 0.231954 11.00000 0.03469 0.04864 = 0.05371 -0.00860 -0.00714 -0.00371 AFIX 23 H3A 2 0.063828 0.384397 0.353183 11.00000 -1.20000 H3B 2 0.065318 0.394343 0.096609 11.00000 -1.20000 AFIX 0 C4 1 0.068117 0.527490 0.252059 11.00000 0.03500 0.05611 = 0.07374 -0.01197 -0.00884 0.00647 AFIX 23 H4A 2 0.078731 0.560114 0.114617 11.00000 -1.20000 H4B 2 0.018802 0.535396 0.280683 11.00000 -1.20000 AFIX 0 C5 1 0.109399 0.574395 0.435684 11.00000 0.03963 0.04733 = 0.07020 -0.01873 0.00092 0.00936 AFIX 23 H5A 2 0.102965 0.644761 0.430328 11.00000 -1.20000 H5B 2 0.091738 0.551339 0.575636 11.00000 -1.20000 AFIX 0 C6 1 0.214261 0.597794 0.224177 11.00000 0.04569 0.02497 = 0.04765 -0.00023 -0.00664 0.00324 AFIX 23 H6A 2 0.202609 0.666861 0.223170 11.00000 -1.20000 H6B 2 0.194076 0.568104 0.094282 11.00000 -1.20000 AFIX 0 C7 1 0.291842 0.586165 0.217850 11.00000 0.04343 0.02481 = 0.04340 0.00279 0.00026 -0.00256 AFIX 23 H7A 2 0.309990 0.614154 0.083146 11.00000 -1.20000 H7B 2 0.312591 0.620682 0.340659 11.00000 -1.20000 AFIX 0 C8 1 0.373959 0.457653 0.148927 11.00000 0.03383 0.03225 = 0.02475 0.00145 -0.00477 -0.00406 C9 1 0.399145 0.352586 0.176136 11.00000 0.03153 0.03361 = 0.03547 0.00187 -0.00259 0.00136 AFIX 13 H9 2 0.388004 0.317917 0.039722 11.00000 -1.20000 AFIX 0 C10 1 0.362294 0.298362 0.362570 11.00000 0.04218 0.03397 = 0.04190 0.00943 -0.00198 0.00603 AFIX 23 H10A 2 0.367869 0.228491 0.340627 11.00000 -1.20000 H10B 2 0.384533 0.315214 0.500456 11.00000 -1.20000 AFIX 0 C11 1 0.277116 0.424894 0.411565 11.00000 0.03376 0.03034 = 0.02349 0.00131 -0.00394 -0.00207 C12 1 0.196253 0.445141 0.424132 11.00000 0.03415 0.03262 = 0.02661 -0.00413 -0.00082 -0.00249 C13 1 0.311403 0.458203 0.627350 11.00000 0.04316 0.05452 = 0.02850 -0.00119 -0.00803 -0.00467 AFIX 137 H13A 2 0.360670 0.464542 0.605946 11.00000 -1.50000 H13B 2 0.302531 0.410629 0.739916 11.00000 -1.50000 H13C 2 0.292396 0.520217 0.670793 11.00000 -1.50000 AFIX 0 C14 1 0.170183 0.402745 0.644337 11.00000 0.04406 0.06123 = 0.03143 -0.00016 0.00677 -0.00554 AFIX 137 H14A 2 0.192999 0.341520 0.672425 11.00000 -1.50000 H14B 2 0.120838 0.392524 0.636722 11.00000 -1.50000 H14C 2 0.180506 0.447838 0.760747 11.00000 -1.50000 AFIX 0 C15 1 0.478730 0.346816 0.206565 11.00000 0.03542 0.04641 = 0.05593 -0.00240 -0.00928 0.00488 AFIX 23 H15A 2 0.491947 0.392899 0.320313 11.00000 -1.20000 H15B 2 0.490217 0.281818 0.259337 11.00000 -1.20000 AFIX 0 C16 1 0.522163 0.367273 0.006653 11.00000 0.03418 0.04423 = 0.08686 0.00779 0.00890 0.00073 AFIX 23 H16A 2 0.570658 0.371939 0.049361 11.00000 -1.20000 H16B 2 0.508477 0.429731 -0.055502 11.00000 -1.20000 AFIX 0 N1 3 0.288400 0.320725 0.378259 11.00000 0.03761 0.02856 = 0.03341 0.00632 -0.00151 -0.00119 N2 3 0.160568 0.401468 0.232814 11.00000 0.03438 0.03077 = 0.03231 -0.00349 -0.00606 -0.00218 N3 3 0.184785 0.551868 0.420810 11.00000 0.03578 0.03538 = 0.03987 -0.01055 -0.00001 0.00135 N4 3 0.309942 0.482033 0.229319 11.00000 0.03456 0.02413 = 0.03016 0.00205 0.00037 -0.00071 O1 4 0.409130 0.516964 0.046302 11.00000 0.04214 0.04058 = 0.05466 0.01126 0.00779 -0.00731 CL1 5 0.512826 0.273663 -0.197925 11.00000 0.06105 0.07464 = 0.05664 0.00480 0.00947 0.00493 HKLF 4 1.0 0.00 0.00 1.00 0.00 -1.00 0.00 1.00 0.00 0.00 REM NC526-a at 297 K in Pna2(1) (#33 in standard setting) REM R1 = 0.0428 for 2434 Fo > 4sig(Fo) and 0.0533 for all 2980 data REM 201 parameters refined using 1 restraints END WGHT 0.0655 0.0000 REM Highest difference peak 0.314, deepest hole -0.136, 1-sigma level 0.054 Q1 1 0.5073 0.3398 -0.1970 11.00000 0.05 0.31 Q2 1 0.1489 0.5618 0.4219 11.00000 0.05 0.30 Q3 1 0.2355 0.4385 0.4200 11.00000 0.05 0.26 Q4 1 0.1802 0.4234 0.3154 11.00000 0.05 0.26 Q5 1 0.2959 0.4422 0.5083 11.00000 0.05 0.25 Q6 1 0.2994 0.5240 0.2227 11.00000 0.05 0.25 Q7 1 0.2708 0.3008 0.2857 11.00000 0.05 0.24 Q8 1 0.3381 0.4758 0.2140 11.00000 0.05 0.24 Q9 1 0.1816 0.4319 0.5264 11.00000 0.05 0.23 Q10 1 0.4355 0.3498 0.1927 11.00000 0.05 0.23 Q11 1 0.2975 0.4500 0.3158 11.00000 0.05 0.23 Q12 1 0.1232 0.4065 0.2493 11.00000 0.05 0.23 Q13 1 0.1870 0.4946 0.4200 11.00000 0.05 0.23 Q14 1 0.0749 0.4755 0.2206 11.00000 0.05 0.22 Q15 1 0.3341 0.4682 0.1656 11.00000 0.05 0.22 Q16 1 0.4636 0.2706 -0.2018 11.00000 0.05 0.22 Q17 1 0.1685 0.3678 0.2206 11.00000 0.05 0.22 Q18 1 0.2531 0.5924 0.2152 11.00000 0.05 0.21 Q19 1 0.3204 0.3137 0.3818 11.00000 0.05 0.21 Q20 1 0.3880 0.3973 0.1528 11.00000 0.05 0.21 Q21 1 0.3819 0.3450 0.2869 11.00000 0.05 0.21 Q22 1 0.1952 0.5745 0.3325 11.00000 0.05 0.21 Q23 1 0.2136 0.2896 0.2247 11.00000 0.05 0.20 Q24 1 0.2833 0.3545 0.4168 11.00000 0.05 0.19 Q25 1 0.1699 0.4228 0.1229 11.00000 0.05 0.18 ; #END Tags that were not found in dictionaries loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, z+1/2' '-x+1/2, y+1/2, z+1/2' 'x+1/2, -y+1/2, 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_symmetry_multiplicity _atom_site_calc_flag _atom_site_refinement_flags C1 C 0.25084(10) 0.28011(13) 0.1885(4) 0.0372(5) Uani 1 1 d . H1A H 0.2598 0.2104 0.1784 0.045 Uiso 1 1 calc R H1B H 0.2677 0.3106 0.0549 0.045 Uiso 1 1 calc R C2 C 0.17417(10) 0.29728(14) 0.2098(4) 0.0383(5) Uani 1 1 d . H2A H 0.1505 0.2724 0.0808 0.046 Uiso 1 1 calc R H2B H 0.1565 0.2627 0.3372 0.046 Uiso 1 1 calc R C3 C 0.08504(10) 0.41947(16) 0.2320(4) 0.0457(5) Uani 1 1 d . H3A H 0.0638 0.3844 0.3532 0.055 Uiso 1 1 calc R H3B H 0.0653 0.3943 0.0966 0.055 Uiso 1 1 calc R C4 C 0.06812(11) 0.52749(17) 0.2521(5) 0.0550(7) Uani 1 1 d . H4A H 0.0787 0.5601 0.1146 0.066 Uiso 1 1 calc R H4B H 0.0188 0.5354 0.2807 0.066 Uiso 1 1 calc R C5 C 0.10940(11) 0.57440(17) 0.4357(5) 0.0524(6) Uani 1 1 d . H5A H 0.103 0.6448 0.4303 0.063 Uiso 1 1 calc R H5B H 0.0917 0.5513 0.5756 0.063 Uiso 1 1 calc R C6 C 0.21426(10) 0.59779(14) 0.2242(4) 0.0394(5) Uani 1 1 d . H6A H 0.2026 0.6669 0.2232 0.047 Uiso 1 1 calc R H6B H 0.1941 0.5681 0.0943 0.047 Uiso 1 1 calc R C7 C 0.29184(10) 0.58616(13) 0.2179(4) 0.0372(5) Uani 1 1 d . H7A H 0.31 0.6142 0.0831 0.045 Uiso 1 1 calc R H7B H 0.3126 0.6207 0.3407 0.045 Uiso 1 1 calc R C8 C 0.37396(9) 0.45765(13) 0.1489(3) 0.0303(4) Uani 1 1 d . C9 C 0.39914(9) 0.35259(13) 0.1761(4) 0.0335(4) Uani 1 1 d . H9 H 0.388 0.3179 0.0397 0.04 Uiso 1 1 calc R C10 C 0.36229(10) 0.29836(14) 0.3626(4) 0.0393(5) Uani 1 1 d . H10A H 0.3679 0.2285 0.3406 0.047 Uiso 1 1 calc R H10B H 0.3845 0.3152 0.5005 0.047 Uiso 1 1 calc R C11 C 0.27712(9) 0.42489(13) 0.4116(3) 0.0292(4) Uani 1 1 d . C12 C 0.19625(10) 0.44514(14) 0.4241(3) 0.0311(4) Uani 1 1 d . C13 C 0.31140(11) 0.45820(16) 0.6273(4) 0.0421(5) Uani 1 1 d . H13A H 0.3607 0.4645 0.6059 0.063 Uiso 1 1 calc R H13B H 0.3025 0.4106 0.7399 0.063 Uiso 1 1 calc R H13C H 0.2924 0.5202 0.6708 0.063 Uiso 1 1 calc R C14 C 0.17018(11) 0.40275(19) 0.6443(4) 0.0456(5) Uani 1 1 d . H14A H 0.193 0.3415 0.6724 0.068 Uiso 1 1 calc R H14B H 0.1208 0.3925 0.6367 0.068 Uiso 1 1 calc R H14C H 0.1805 0.4478 0.7607 0.068 Uiso 1 1 calc R C15 C 0.47873(10) 0.34682(17) 0.2066(4) 0.0459(6) Uani 1 1 d . H15A H 0.4919 0.3929 0.3203 0.055 Uiso 1 1 calc R H15B H 0.4902 0.2818 0.2593 0.055 Uiso 1 1 calc R C16 C 0.52216(11) 0.36727(18) 0.0067(6) 0.0551(7) Uani 1 1 d . H16A H 0.5707 0.3719 0.0494 0.066 Uiso 1 1 calc R H16B H 0.5085 0.4297 -0.0555 0.066 Uiso 1 1 calc R N1 N 0.28840(8) 0.32072(11) 0.3783(3) 0.0332(4) Uani 1 1 d . N2 N 0.16057(8) 0.40147(11) 0.2328(3) 0.0325(4) Uani 1 1 d . N3 N 0.18478(8) 0.55187(12) 0.4208(3) 0.0370(4) Uani 1 1 d . N4 N 0.30994(8) 0.48203(10) 0.2293(3) 0.0296(3) Uani 1 1 d . O1 O 0.40913(8) 0.51696(10) 0.0463(3) 0.0458(4) Uani 1 1 d . Cl1 Cl 0.51283(3) 0.27366(5) -0.19792(14) 0.0641(2) 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 0.0463(11) 0.0251(8) 0.0401(12) -0.0023(8) -0.0006(10) -0.0031(7) C2 0.0444(11) 0.0301(9) 0.0404(12) -0.0053(9) -0.0023(10) -0.0082(7) C3 0.0347(10) 0.0486(12) 0.0537(14) -0.0086(11) -0.0071(10) -0.0037(8) C4 0.0350(10) 0.0561(13) 0.0737(19) -0.0120(14) -0.0088(12) 0.0065(9) C5 0.0396(11) 0.0473(12) 0.0702(18) -0.0187(13) 0.0009(12) 0.0094(9) C6 0.0457(11) 0.0250(9) 0.0476(13) -0.0002(9) -0.0066(10) 0.0032(7) C7 0.0434(11) 0.0248(9) 0.0434(12) 0.0028(9) 0.0003(10) -0.0026(7) C8 0.0338(9) 0.0322(9) 0.0247(9) 0.0014(8) -0.0048(8) -0.0041(7) C9 0.0315(9) 0.0336(9) 0.0355(11) 0.0019(8) -0.0026(8) 0.0014(7) C10 0.0422(11) 0.0340(10) 0.0419(13) 0.0094(9) -0.0020(9) 0.0060(8) C11 0.0338(9) 0.0303(9) 0.0235(9) 0.0013(8) -0.0039(8) -0.0021(7) C12 0.0341(9) 0.0326(10) 0.0266(9) -0.0041(8) -0.0008(8) -0.0025(7) C13 0.0432(11) 0.0545(13) 0.0285(11) -0.0012(10) -0.0080(9) -0.0047(9) C14 0.0441(12) 0.0612(14) 0.0314(11) -0.0002(11) 0.0068(10) -0.0055(9) C15 0.0354(10) 0.0464(11) 0.0559(15) -0.0024(11) -0.0093(10) 0.0049(8) C16 0.0342(11) 0.0442(12) 0.087(2) 0.0078(13) 0.0089(12) 0.0007(9) N1 0.0376(8) 0.0286(8) 0.0334(9) 0.0063(7) -0.0015(7) -0.0012(6) N2 0.0344(8) 0.0308(7) 0.0323(9) -0.0035(7) -0.0061(7) -0.0022(6) N3 0.0358(8) 0.0354(9) 0.0399(10) -0.0106(8) 0.0000(8) 0.0013(6) N4 0.0346(8) 0.0241(7) 0.0302(8) 0.0021(7) 0.0004(7) -0.0007(6) O1 0.0421(8) 0.0406(8) 0.0547(10) 0.0113(8) 0.0078(7) -0.0073(6) Cl1 0.0611(4) 0.0746(4) 0.0566(4) 0.0048(4) 0.0095(4) 0.0049(3) 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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Cl Cl 0.1484 0.1585 '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 0.05 0 0 -1 0.02 0 1 0 0.15 0 -1 0 0.13 -1 0 0 0.16 1 0 0 0.19 4 -1 24 0.085 -1 17 12 0.13 -2 -1 -3 0.125 2 2 -5 0.16 -2 -1 2 0.14 2 -3 -1 0.205 -1 14 -19 0.105 2 -1 1 0.19 1 -6 10 0.115 1 1 1 0.195 0 -3 4 0.115 loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle N1 C1 C2 110.85(18) N1 C1 H1A 109.5 C2 C1 H1A 109.5 N1 C1 H1B 109.5 C2 C1 H1B 109.5 H1A C1 H1B 108.1 N2 C2 C1 109.78(15) N2 C2 H2A 109.7 C1 C2 H2A 109.7 N2 C2 H2B 109.7 C1 C2 H2B 109.7 H2A C2 H2B 108.2 N2 C3 C4 111.95(16) N2 C3 H3A 109.2 C4 C3 H3A 109.2 N2 C3 H3B 109.2 C4 C3 H3B 109.2 H3A C3 H3B 107.9 C5 C4 C3 111.1(2) C5 C4 H4A 109.4 C3 C4 H4A 109.4 C5 C4 H4B 109.4 C3 C4 H4B 109.4 H4A C4 H4B 108 N3 C5 C4 112.27(19) N3 C5 H5A 109.1 C4 C5 H5A 109.1 N3 C5 H5B 109.1 C4 C5 H5B 109.1 H5A C5 H5B 107.9 N3 C6 C7 111.09(17) N3 C6 H6A 109.4 C7 C6 H6A 109.4 N3 C6 H6B 109.4 C7 C6 H6B 109.4 H6A C6 H6B 108 N4 C7 C6 109.72(15) N4 C7 H7A 109.7 C6 C7 H7A 109.7 N4 C7 H7B 109.7 C6 C7 H7B 109.7 H7A C7 H7B 108.2 O1 C8 N4 121.21(17) O1 C8 C9 120.17(18) N4 C8 C9 118.49(15) C8 C9 C10 112.94(16) C8 C9 C15 112.09(16) C10 C9 C15 110.20(17) C8 C9 H9 107.1 C10 C9 H9 107.1 C15 C9 H9 107.1 N1 C10 C9 113.51(16) N1 C10 H10A 108.9 C9 C10 H10A 108.9 N1 C10 H10B 108.9 C9 C10 H10B 108.9 H10A C10 H10B 107.7 N1 C11 N4 110.14(15) N1 C11 C13 110.16(16) N4 C11 C13 107.36(14) N1 C11 C12 108.95(13) N4 C11 C12 111.06(14) C13 C11 C12 109.15(16) N3 C12 N2 108.60(16) N3 C12 C14 109.53(17) N2 C12 C14 112.48(15) N3 C12 C11 108.62(14) N2 C12 C11 110.34(15) C14 C12 C11 107.19(16) C11 C13 H13A 109.5 C11 C13 H13B 109.5 H13A C13 H13B 109.5 C11 C13 H13C 109.5 H13A C13 H13C 109.5 H13B C13 H13C 109.5 C12 C14 H14A 109.5 C12 C14 H14B 109.5 H14A C14 H14B 109.5 C12 C14 H14C 109.5 H14A C14 H14C 109.5 H14B C14 H14C 109.5 C16 C15 C9 116.4(2) C16 C15 H15A 108.2 C9 C15 H15A 108.2 C16 C15 H15B 108.2 C9 C15 H15B 108.2 H15A C15 H15B 107.3 C15 C16 Cl1 111.98(16) C15 C16 H16A 109.2 Cl1 C16 H16A 109.2 C15 C16 H16B 109.2 Cl1 C16 H16B 109.2 H16A C16 H16B 107.9 C11 N1 C10 111.11(14) C11 N1 C1 113.93(15) C10 N1 C1 110.37(17) C2 N2 C3 109.90(15) C2 N2 C12 112.82(15) C3 N2 C12 113.14(16) C6 N3 C12 112.13(16) C6 N3 C5 109.79(19) C12 N3 C5 110.50(15) C8 N4 C7 115.68(14) C8 N4 C11 121.24(14) C7 N4 C11 116.20(16) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance C1 N1 1.471(3) C1 C2 1.498(3) C1 H1A 0.97 C1 H1B 0.97 C2 N2 1.454(2) C2 H2A 0.97 C2 H2B 0.97 C3 N2 1.473(2) C3 C4 1.516(3) C3 H3A 0.97 C3 H3B 0.97 C4 C5 1.514(4) C4 H4A 0.97 C4 H4B 0.97 C5 N3 1.484(3) C5 H5A 0.97 C5 H5B 0.97 C6 N3 1.466(3) C6 C7 1.500(3) C6 H6A 0.97 C6 H6B 0.97 C7 N4 1.467(2) C7 H7A 0.97 C7 H7B 0.97 C8 O1 1.227(2) C8 N4 1.366(2) C8 C9 1.524(2) C9 C10 1.530(3) C9 C15 1.543(3) C9 H9 0.98 C10 N1 1.456(2) C10 H10A 0.97 C10 H10B 0.97 C11 N1 1.454(2) C11 N4 1.497(2) C11 C13 1.539(3) C11 C12 1.581(3) C12 N3 1.475(3) C12 N2 1.478(2) C12 C14 1.544(3) C13 H13A 0.96 C13 H13B 0.96 C13 H13C 0.96 C14 H14A 0.96 C14 H14B 0.96 C14 H14C 0.96 C15 C16 1.502(4) C15 H15A 0.97 C15 H15B 0.97 C16 Cl1 1.795(3) C16 H16A 0.97 C16 H16B 0.97