#------------------------------------------------------------------------------ #$Date: 2017-06-01 08:18:58 +0300 (Thu, 01 Jun 2017) $ #$Revision: 197130 $ #$URL: file:///home/coder/svn-repositories/cod/cif/7/22/83/7228349.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_7228349 loop_ _publ_author_name 'Castillo, Juan-Carlos' 'Rosero, Hern\'an-Alejandro' 'Portilla, Jaime' _publ_section_title ; Simple access toward 3-halo- and 3-nitro-pyrazolo[1,5-a]pyrimidines through a one-pot sequence ; _journal_issue 45 _journal_name_full 'RSC Adv.' _journal_page_first 28483 _journal_paper_doi 10.1039/C7RA04336H _journal_volume 7 _journal_year 2017 _chemical_formula_moiety 'C13 H9 Cl I N3' _chemical_formula_sum 'C13 H9 Cl I N3' _chemical_formula_weight 369.58 _chemical_melting_point 430 _chemical_name_systematic 7-(4-Chlorophenyl)-3-iodo-2-methylpyrazolo[1,5-a]pyrimidine _space_group_crystal_system triclinic _space_group_IT_number 2 _space_group_name_Hall '-P 1' _space_group_name_H-M_alt 'P -1' _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _atom_sites_solution_hydrogens geom _atom_sites_solution_primary iterative _atom_sites_solution_secondary difmap _audit_creation_method SHELXL-2014 _audit_update_record ; 2017-04-06 deposited with the CCDC. 2017-05-22 downloaded from the CCDC. ; _cell_angle_alpha 105.748(5) _cell_angle_beta 105.605(6) _cell_angle_gamma 99.832(6) _cell_formula_units_Z 4 _cell_length_a 8.1315(6) _cell_length_b 12.4851(8) _cell_length_c 14.5014(7) _cell_measurement_reflns_used 18407 _cell_measurement_temperature 298(2) _cell_measurement_theta_max 29.390 _cell_measurement_theta_min 3.302 _cell_volume 1316.70(16) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01) ; _computing_molecular_graphics 'Mercury (Macrae et al., 2008)' _computing_publication_material 'SHELXL-2014 (Sheldrick, 2015)' _computing_structure_refinement 'SHELXL-2014 (Sheldrick, 2015)' _computing_structure_solution 'Superflip (Palatinus & Chapuis, 2007)' _diffrn_ambient_temperature 298(2) _diffrn_detector 'CCD plate' _diffrn_detector_area_resol_mean 5.3072 _diffrn_detector_type Atlas _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.920 _diffrn_measurement_device 'four-circle diffractometer' _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Atlas' _diffrn_measurement_method '\w scans' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0727 _diffrn_reflns_av_unetI/netI 0.0311 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.920 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_l_max 20 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_number 58640 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.920 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 30.484 _diffrn_reflns_theta_min 3.005 _diffrn_source 'SuperNova (Mo) X-ray Source' _exptl_absorpt_coefficient_mu 2.619 _exptl_absorpt_correction_T_max 1.00000 _exptl_absorpt_correction_T_min 0.74510 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.37.35 (release 13-08-2014 CrysAlis171 .NET) (compiled Aug 13 2014,18:06:01) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_crystal_colour yellow _exptl_crystal_density_diffrn 1.864 _exptl_crystal_density_method 'not measured' _exptl_crystal_description parallelepiped _exptl_crystal_F_000 712 _exptl_crystal_recrystallization_method 'Re-crystallisation from solvent: Methanol' _exptl_crystal_size_max 0.263 _exptl_crystal_size_mid 0.137 _exptl_crystal_size_min 0.084 _refine_diff_density_max 0.620 _refine_diff_density_min -0.751 _refine_diff_density_rms 0.079 _refine_ls_extinction_coef 0.0014(3) _refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^ _refine_ls_extinction_method SHELXL _refine_ls_goodness_of_fit_ref 1.090 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 328 _refine_ls_number_reflns 7387 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.090 _refine_ls_R_factor_all 0.0589 _refine_ls_R_factor_gt 0.0368 _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^)+(0.0361P)^2^+0.8410P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0883 _refine_ls_wR_factor_ref 0.1068 _reflns_Friedel_coverage 0.000 _reflns_number_gt 5196 _reflns_number_total 7387 _reflns_threshold_expression 'I > 2\s(I)' _cod_data_source_file c7ra04336h2.cif _cod_data_source_block shelxs _cod_original_cell_volume 1316.71(15) _cod_database_code 7228349 _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_min 0.546 _shelx_estimated_absorpt_t_max 0.810 _shelxl_version_number 2014-3 _shelx_res_file ; TITL 2016Uniandes013_Mo_2907 in P-1 REM TITL 2016Uniandes013_Mo_2907 in P-1 CELL 0.71073 8.13155 12.48514 14.50142 105.74839 105.60519 99.83170 ZERR 2 0.0006 0.0008 0.0007 0.0051 0.0059 0.0061 LATT 1 SFAC C H N CL I UNIT 52. 36. 12. 4. 4. LIST 4 ! automatically inserted. Change 6 to 4 for CHECKCIF!! L.S. 10 FMAP 2 PLAN 10 TEMP 25 SIZE 0.084 0.137 0.263 ACTA CONF BOND $H HTAB EQIV $1 -x+1, -y+1, -z+1 HTAB C8 N26_$1 EQIV $2 -x, -y+1, -z HTAB C37 N19_$2 WGHT 0.036100 0.841000 EXTI 0.001383 FVAR 2.62190 I1 5 0.157293 0.102678 0.122194 11.00000 0.06810 0.04986 = 0.06679 0.00449 -0.00302 -0.01082 C2 1 0.351380 0.252567 0.208763 11.00000 0.04371 0.03768 = 0.04420 0.00486 0.00488 -0.00103 C4 1 0.391423 0.347695 0.179118 11.00000 0.04497 0.04758 = 0.03624 0.00847 0.00508 0.00590 N5 3 0.524095 0.429045 0.263290 11.00000 0.04309 0.04114 = 0.03595 0.01035 0.00470 0.00317 N6 3 0.567376 0.389711 0.343118 11.00000 0.04772 0.04296 = 0.03870 0.01078 0.00320 -0.00017 C7 1 0.460976 0.282372 0.309297 11.00000 0.04907 0.04203 = 0.04318 0.01135 0.00816 0.00373 C8 1 0.465915 0.211345 0.376302 11.00000 0.07457 0.05758 = 0.05937 0.02415 0.00001 -0.00881 AFIX 137 H8A 2 0.348713 0.184198 0.377156 11.00000 -1.50000 H8B 2 0.542347 0.257133 0.443948 11.00000 -1.50000 H8C 2 0.509886 0.146640 0.351260 11.00000 -1.50000 AFIX 0 C9 1 0.591395 0.537686 0.262928 11.00000 0.04467 0.04334 = 0.04551 0.01393 0.01284 0.00823 C10 1 0.725512 0.624846 0.354865 11.00000 0.04393 0.03906 = 0.04737 0.01263 0.01336 0.00541 C11 1 0.860352 0.599404 0.419615 11.00000 0.04735 0.04077 = 0.05022 0.01155 0.01208 0.00487 AFIX 43 H11 2 0.867897 0.523540 0.406121 11.00000 -1.20000 AFIX 0 C12 1 0.984551 0.685064 0.504342 11.00000 0.05109 0.05406 = 0.04981 0.01634 0.01062 0.00431 AFIX 43 H12 2 1.075849 0.667489 0.547050 11.00000 -1.20000 AFIX 0 C13 1 0.969967 0.796338 0.523879 11.00000 0.06105 0.05015 = 0.04953 0.00358 0.01330 -0.00025 CL14 4 1.117535 0.903261 0.633551 11.00000 0.10191 0.06575 = 0.07019 -0.01317 -0.00204 -0.00557 C15 1 0.838839 0.824261 0.461004 11.00000 0.08161 0.03618 = 0.07315 0.00299 0.01799 0.01167 AFIX 43 H15 2 0.831291 0.900180 0.475666 11.00000 -1.20000 AFIX 0 C16 1 0.717701 0.739255 0.375661 11.00000 0.05923 0.04688 = 0.07235 0.01622 0.01253 0.01399 AFIX 43 H16 2 0.630300 0.758387 0.331736 11.00000 -1.20000 AFIX 0 C17 1 0.522844 0.556732 0.173914 11.00000 0.05776 0.05775 = 0.05549 0.02735 0.01305 0.00914 AFIX 43 H17 2 0.563711 0.628123 0.168250 11.00000 -1.20000 AFIX 0 C18 1 0.391444 0.470133 0.090666 11.00000 0.06298 0.06979 = 0.04850 0.02746 0.00602 0.00976 AFIX 43 H18 2 0.349376 0.486787 0.031279 11.00000 -1.20000 AFIX 0 N19 3 0.324284 0.367197 0.091398 11.00000 0.05689 0.06234 = 0.04241 0.01631 0.00264 0.00656 I20 5 0.312730 0.894595 0.384404 11.00000 0.07104 0.04298 = 0.06157 0.00513 0.00068 -0.00105 C21 1 0.153098 0.734445 0.290796 11.00000 0.05029 0.04093 = 0.03913 0.00644 0.00772 0.00095 C22 1 0.010959 0.708558 0.201464 11.00000 0.05338 0.04307 = 0.04217 0.01195 0.00879 0.00523 N23 3 -0.063826 0.595043 0.159066 11.00000 0.05179 0.04411 = 0.04044 0.01421 0.00605 0.00673 N24 3 0.030917 0.547761 0.222751 11.00000 0.04769 0.04174 = 0.03610 0.01070 0.01079 0.00640 C25 1 0.165096 0.630693 0.305437 11.00000 0.04397 0.04574 = 0.03711 0.00940 0.00963 0.00561 N26 3 0.269898 0.604066 0.381023 11.00000 0.05219 0.05600 = 0.04121 0.01344 0.00892 0.01185 C27 1 0.232290 0.495337 0.374372 11.00000 0.05955 0.05903 = 0.04875 0.02143 0.01548 0.02149 AFIX 43 H27 2 0.298861 0.474683 0.426531 11.00000 -1.20000 AFIX 0 C28 1 0.097256 0.407819 0.293095 11.00000 0.06397 0.04921 = 0.04905 0.01936 0.02132 0.01859 AFIX 43 H28 2 0.077043 0.332198 0.293036 11.00000 -1.20000 AFIX 0 C29 1 -0.004328 0.433340 0.214260 11.00000 0.05277 0.04214 = 0.04189 0.01327 0.01840 0.01018 C30 1 -0.143138 0.347516 0.123780 11.00000 0.05421 0.03814 = 0.04576 0.01117 0.01720 0.01104 C31 1 -0.258178 0.259453 0.135353 11.00000 0.07059 0.04560 = 0.05324 0.01282 0.02645 0.00697 AFIX 43 H31 2 -0.248984 0.256568 0.199911 11.00000 -1.20000 AFIX 0 C32 1 -0.386283 0.176181 0.050622 11.00000 0.06383 0.04426 = 0.07727 0.01137 0.02647 -0.00077 AFIX 43 H32 2 -0.464791 0.118292 0.058172 11.00000 -1.20000 AFIX 0 C33 1 -0.396246 0.179780 -0.043371 11.00000 0.05383 0.04624 = 0.06023 0.00262 0.00916 0.01084 CL34 4 -0.556603 0.075483 -0.150332 11.00000 0.07324 0.06805 = 0.08154 -0.00506 -0.00761 0.00160 C35 1 -0.282172 0.263984 -0.057087 11.00000 0.07130 0.05699 = 0.04641 0.01265 0.01243 0.01447 AFIX 43 H35 2 -0.289887 0.264349 -0.122156 11.00000 -1.20000 AFIX 0 C36 1 -0.155910 0.348080 0.026896 11.00000 0.06737 0.04871 = 0.04619 0.01402 0.01540 0.00315 AFIX 43 H36 2 -0.078659 0.405694 0.018239 11.00000 -1.20000 AFIX 0 C37 1 -0.061823 0.790841 0.156136 11.00000 0.07716 0.05180 = 0.05925 0.01836 0.00193 0.01358 AFIX 137 H37A 2 -0.148781 0.749000 0.090449 11.00000 -1.50000 H37B 2 0.032105 0.842837 0.149253 11.00000 -1.50000 H37C 2 -0.115872 0.833911 0.199384 11.00000 -1.50000 AFIX 0 HKLF 4 REM 2016Uniandes013_Mo_2907 in P-1 REM R1 = 0.0368 for 5196 Fo > 4sig(Fo) and 0.0589 for all 7387 data REM 328 parameters refined using 0 restraints END WGHT 0.0361 0.8410 REM Instructions for potential hydrogen bonds HTAB C8 N26_$1 HTAB C37 N19_$2 REM Highest difference peak 0.620, deepest hole -0.751, 1-sigma level 0.079 Q1 1 0.2238 0.1042 0.0855 11.00000 0.05 0.62 Q2 1 0.2030 0.8199 0.3756 11.00000 0.05 0.55 Q3 1 0.0935 0.0607 0.0396 11.00000 0.05 0.52 Q4 1 0.3860 0.9421 0.4646 11.00000 0.05 0.51 Q5 1 0.2479 0.8419 0.3037 11.00000 0.05 0.48 Q6 1 0.3164 0.8988 0.4132 11.00000 0.05 0.47 Q7 1 0.1567 0.1029 0.1553 11.00000 0.05 0.46 Q8 1 0.3706 0.8986 0.3488 11.00000 0.05 0.46 Q9 1 -0.5861 0.0762 -0.0989 11.00000 0.05 0.45 Q10 1 1.1046 0.9256 0.6053 11.00000 0.05 0.41 ; _shelx_res_checksum 10653 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 I1 I 0.15729(3) 0.10268(2) 0.12219(2) 0.07369(11) Uani 1 1 d . . C2 C 0.3514(4) 0.2526(2) 0.2088(2) 0.0474(6) Uani 1 1 d . . C4 C 0.3914(4) 0.3477(3) 0.1791(2) 0.0467(6) Uani 1 1 d . . N5 N 0.5241(3) 0.4290(2) 0.26329(16) 0.0434(5) Uani 1 1 d . . N6 N 0.5674(3) 0.3897(2) 0.34312(17) 0.0477(6) Uani 1 1 d . . C7 C 0.4610(4) 0.2824(3) 0.3093(2) 0.0480(6) Uani 1 1 d . . C8 C 0.4659(5) 0.2113(3) 0.3763(3) 0.0710(10) Uani 1 1 d . . H8A H 0.3487 0.1842 0.3772 0.107 Uiso 1 1 calc R U H8B H 0.5423 0.2571 0.4439 0.107 Uiso 1 1 calc R U H8C H 0.5099 0.1466 0.3513 0.107 Uiso 1 1 calc R U C9 C 0.5914(4) 0.5377(2) 0.2629(2) 0.0456(6) Uani 1 1 d . . C10 C 0.7255(4) 0.6248(2) 0.3549(2) 0.0450(6) Uani 1 1 d . . C11 C 0.8604(4) 0.5994(2) 0.4196(2) 0.0487(6) Uani 1 1 d . . H11 H 0.8679 0.5235 0.4061 0.058 Uiso 1 1 calc R U C12 C 0.9846(4) 0.6851(3) 0.5043(2) 0.0544(7) Uani 1 1 d . . H12 H 1.0758 0.6675 0.5471 0.065 Uiso 1 1 calc R U C13 C 0.9700(5) 0.7963(3) 0.5239(2) 0.0594(8) Uani 1 1 d . . Cl14 Cl 1.11753(18) 0.90326(9) 0.63355(8) 0.0972(4) Uani 1 1 d . . C15 C 0.8388(5) 0.8243(3) 0.4610(3) 0.0691(10) Uani 1 1 d . . H15 H 0.8313 0.9002 0.4757 0.083 Uiso 1 1 calc R U C16 C 0.7177(5) 0.7393(3) 0.3757(3) 0.0623(8) Uani 1 1 d . . H16 H 0.6303 0.7584 0.3317 0.075 Uiso 1 1 calc R U C17 C 0.5228(4) 0.5567(3) 0.1739(2) 0.0572(8) Uani 1 1 d . . H17 H 0.5637 0.6281 0.1683 0.069 Uiso 1 1 calc R U C18 C 0.3914(5) 0.4701(3) 0.0907(2) 0.0624(9) Uani 1 1 d . . H18 H 0.3494 0.4868 0.0313 0.075 Uiso 1 1 calc R U N19 N 0.3243(4) 0.3672(2) 0.09140(19) 0.0583(7) Uani 1 1 d . . I20 I 0.31273(3) 0.89460(2) 0.38440(2) 0.06784(11) Uani 1 1 d . . C21 C 0.1531(4) 0.7344(2) 0.2908(2) 0.0479(6) Uani 1 1 d . . C22 C 0.0110(4) 0.7086(3) 0.2015(2) 0.0492(7) Uani 1 1 d . . N23 N -0.0638(3) 0.5950(2) 0.15907(18) 0.0482(6) Uani 1 1 d . . N24 N 0.0309(3) 0.5478(2) 0.22275(16) 0.0437(5) Uani 1 1 d . . C25 C 0.1651(4) 0.6307(2) 0.3054(2) 0.0449(6) Uani 1 1 d . . N26 N 0.2699(3) 0.6041(2) 0.38102(18) 0.0521(6) Uani 1 1 d . . C27 C 0.2323(4) 0.4953(3) 0.3744(2) 0.0548(7) Uani 1 1 d . . H27 H 0.2989 0.4747 0.4265 0.066 Uiso 1 1 calc R U C28 C 0.0973(4) 0.4078(3) 0.2931(2) 0.0524(7) Uani 1 1 d . . H28 H 0.0770 0.3322 0.2930 0.063 Uiso 1 1 calc R U C29 C -0.0043(4) 0.4333(2) 0.2143(2) 0.0455(6) Uani 1 1 d . . C30 C -0.1431(4) 0.3475(2) 0.1238(2) 0.0467(6) Uani 1 1 d . . C31 C -0.2582(5) 0.2595(3) 0.1354(3) 0.0571(8) Uani 1 1 d . . H31 H -0.2490 0.2566 0.1999 0.069 Uiso 1 1 calc R U C32 C -0.3863(5) 0.1762(3) 0.0506(3) 0.0650(9) Uani 1 1 d . . H32 H -0.4648 0.1183 0.0582 0.078 Uiso 1 1 calc R U C33 C -0.3962(5) 0.1798(3) -0.0434(3) 0.0591(8) Uani 1 1 d . . Cl34 Cl -0.55660(15) 0.07548(10) -0.15033(9) 0.0901(3) Uani 1 1 d . . C35 C -0.2822(5) 0.2640(3) -0.0571(2) 0.0611(8) Uani 1 1 d . . H35 H -0.2899 0.2643 -0.1222 0.073 Uiso 1 1 calc R U C36 C -0.1559(5) 0.3481(3) 0.0269(2) 0.0568(8) Uani 1 1 d . . H36 H -0.0787 0.4057 0.0182 0.068 Uiso 1 1 calc R U C37 C -0.0618(5) 0.7908(3) 0.1561(3) 0.0676(9) Uani 1 1 d . . H37A H -0.1488 0.7490 0.0904 0.101 Uiso 1 1 calc R U H37B H 0.0321 0.8428 0.1493 0.101 Uiso 1 1 calc R U H37C H -0.1159 0.8339 0.1994 0.101 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 I1 0.06810(18) 0.04986(15) 0.06679(17) 0.00449(11) -0.00302(12) -0.01082(11) C2 0.0437(15) 0.0377(14) 0.0442(14) 0.0049(11) 0.0049(12) -0.0010(11) C4 0.0450(15) 0.0476(16) 0.0362(13) 0.0085(11) 0.0051(11) 0.0059(12) N5 0.0431(12) 0.0411(12) 0.0360(11) 0.0104(9) 0.0047(9) 0.0032(10) N6 0.0477(13) 0.0430(13) 0.0387(12) 0.0108(10) 0.0032(10) -0.0002(10) C7 0.0491(16) 0.0420(15) 0.0432(14) 0.0114(12) 0.0082(12) 0.0037(12) C8 0.075(2) 0.058(2) 0.059(2) 0.0241(16) 0.0000(17) -0.0088(17) C9 0.0447(15) 0.0433(15) 0.0455(14) 0.0139(12) 0.0128(12) 0.0082(12) C10 0.0439(15) 0.0391(14) 0.0474(15) 0.0126(12) 0.0134(12) 0.0054(11) C11 0.0474(16) 0.0408(14) 0.0502(15) 0.0116(12) 0.0121(13) 0.0049(12) C12 0.0511(17) 0.0541(18) 0.0498(16) 0.0163(14) 0.0106(13) 0.0043(14) C13 0.061(2) 0.0502(18) 0.0495(17) 0.0036(14) 0.0133(15) -0.0003(15) Cl14 0.1019(8) 0.0657(6) 0.0702(6) -0.0132(5) -0.0020(6) -0.0056(6) C15 0.082(3) 0.0362(16) 0.073(2) 0.0030(15) 0.018(2) 0.0117(16) C16 0.059(2) 0.0469(18) 0.072(2) 0.0162(16) 0.0125(17) 0.0140(15) C17 0.0578(19) 0.0578(19) 0.0555(17) 0.0274(15) 0.0130(15) 0.0091(15) C18 0.063(2) 0.070(2) 0.0485(17) 0.0275(16) 0.0060(15) 0.0098(17) N19 0.0569(16) 0.0623(17) 0.0424(13) 0.0163(12) 0.0026(11) 0.0066(13) I20 0.07104(18) 0.04298(14) 0.06157(16) 0.00513(10) 0.00068(12) -0.00105(11) C21 0.0503(16) 0.0409(15) 0.0391(13) 0.0064(11) 0.0077(12) 0.0010(12) C22 0.0534(17) 0.0431(15) 0.0422(14) 0.0120(12) 0.0088(13) 0.0052(13) N23 0.0518(14) 0.0441(13) 0.0404(12) 0.0142(10) 0.0061(10) 0.0067(11) N24 0.0477(13) 0.0417(12) 0.0361(11) 0.0107(9) 0.0108(10) 0.0064(10) C25 0.0440(15) 0.0457(15) 0.0371(13) 0.0094(11) 0.0096(11) 0.0056(12) N26 0.0522(15) 0.0560(15) 0.0412(12) 0.0134(11) 0.0089(11) 0.0119(12) C27 0.0596(19) 0.0590(19) 0.0488(16) 0.0214(14) 0.0155(14) 0.0215(15) C28 0.064(2) 0.0492(16) 0.0490(16) 0.0194(13) 0.0213(14) 0.0186(14) C29 0.0528(16) 0.0421(15) 0.0419(14) 0.0133(12) 0.0184(12) 0.0102(12) C30 0.0542(17) 0.0381(14) 0.0458(14) 0.0112(12) 0.0172(13) 0.0110(12) C31 0.071(2) 0.0456(17) 0.0532(17) 0.0128(14) 0.0264(16) 0.0070(15) C32 0.064(2) 0.0443(17) 0.077(2) 0.0114(16) 0.0265(18) -0.0008(15) C33 0.0538(19) 0.0462(17) 0.0602(19) 0.0026(14) 0.0092(15) 0.0108(14) Cl34 0.0732(7) 0.0681(6) 0.0815(6) -0.0051(5) -0.0076(5) 0.0016(5) C35 0.071(2) 0.0570(19) 0.0464(16) 0.0127(14) 0.0124(15) 0.0145(16) C36 0.067(2) 0.0487(17) 0.0462(15) 0.0140(13) 0.0154(14) 0.0031(15) C37 0.077(2) 0.0518(19) 0.0592(19) 0.0184(16) 0.0019(17) 0.0136(17) 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 0.0000 0.0000 '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' Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' I I -0.4742 1.8119 '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 C4 C2 C7 106.4(2) C4 C2 I1 125.6(2) C7 C2 I1 127.9(2) N19 C4 C2 131.7(3) N19 C4 N5 123.2(3) C2 C4 N5 105.1(2) N6 N5 C9 126.4(2) N6 N5 C4 112.2(2) C9 N5 C4 121.2(2) C7 N6 N5 104.7(2) N6 C7 C2 111.5(3) N6 C7 C8 120.9(3) C2 C7 C8 127.5(3) C7 C8 H8A 109.5 C7 C8 H8B 109.5 H8A C8 H8B 109.5 C7 C8 H8C 109.5 H8A C8 H8C 109.5 H8B C8 H8C 109.5 C17 C9 N5 115.1(3) C17 C9 C10 124.4(3) N5 C9 C10 120.4(2) C11 C10 C16 118.6(3) C11 C10 C9 123.5(3) C16 C10 C9 117.9(3) C10 C11 C12 121.1(3) C10 C11 H11 119.4 C12 C11 H11 119.4 C13 C12 C11 118.6(3) C13 C12 H12 120.7 C11 C12 H12 120.7 C15 C13 C12 121.6(3) C15 C13 Cl14 119.3(3) C12 C13 Cl14 119.1(3) C13 C15 C16 119.6(3) C13 C15 H15 120.2 C16 C15 H15 120.2 C15 C16 C10 120.4(3) C15 C16 H16 119.8 C10 C16 H16 119.8 C9 C17 C18 121.0(3) C9 C17 H17 119.5 C18 C17 H17 119.5 N19 C18 C17 124.1(3) N19 C18 H18 117.9 C17 C18 H18 117.9 C18 N19 C4 115.3(3) C25 C21 C22 106.7(3) C25 C21 I20 126.0(2) C22 C21 I20 127.3(2) N23 C22 C21 111.6(3) N23 C22 C37 120.8(3) C21 C22 C37 127.6(3) C22 N23 N24 104.6(2) N23 N24 C29 126.1(2) N23 N24 C25 112.4(2) C29 N24 C25 121.4(2) N26 C25 C21 132.6(3) N26 C25 N24 122.6(3) C21 C25 N24 104.7(2) C27 N26 C25 115.8(3) N26 C27 C28 124.0(3) N26 C27 H27 118.0 C28 C27 H27 118.0 C29 C28 C27 120.4(3) C29 C28 H28 119.8 C27 C28 H28 119.8 C28 C29 N24 115.6(3) C28 C29 C30 124.6(3) N24 C29 C30 119.8(2) C36 C30 C31 118.9(3) C36 C30 C29 121.6(3) C31 C30 C29 119.4(3) C32 C31 C30 120.0(3) C32 C31 H31 120.0 C30 C31 H31 120.0 C33 C32 C31 119.5(3) C33 C32 H32 120.2 C31 C32 H32 120.2 C32 C33 C35 121.7(3) C32 C33 Cl34 119.9(3) C35 C33 Cl34 118.5(3) C33 C35 C36 119.2(3) C33 C35 H35 120.4 C36 C35 H35 120.4 C35 C36 C30 120.6(3) C35 C36 H36 119.7 C30 C36 H36 119.7 C22 C37 H37A 109.5 C22 C37 H37B 109.5 H37A C37 H37B 109.5 C22 C37 H37C 109.5 H37A C37 H37C 109.5 H37B C37 H37C 109.5 loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_distance I1 C2 2.054(3) C2 C4 1.386(4) C2 C7 1.397(4) C4 N19 1.347(4) C4 N5 1.389(3) N5 N6 1.361(3) N5 C9 1.375(4) N6 C7 1.343(4) C7 C8 1.480(4) C8 H8A 0.9600 C8 H8B 0.9600 C8 H8C 0.9600 C9 C17 1.363(4) C9 C10 1.475(4) C10 C11 1.383(4) C10 C16 1.394(4) C11 C12 1.387(4) C11 H11 0.9300 C12 C13 1.373(5) C12 H12 0.9300 C13 C15 1.366(5) C13 Cl14 1.739(3) C15 C16 1.379(5) C15 H15 0.9300 C16 H16 0.9300 C17 C18 1.404(4) C17 H17 0.9300 C18 N19 1.312(4) C18 H18 0.9300 I20 C21 2.054(3) C21 C25 1.383(4) C21 C22 1.399(4) C22 N23 1.337(4) C22 C37 1.484(4) N23 N24 1.365(3) N24 C29 1.373(3) N24 C25 1.392(3) C25 N26 1.353(4) N26 C27 1.310(4) C27 C28 1.408(4) C27 H27 0.9300 C28 C29 1.368(4) C28 H28 0.9300 C29 C30 1.473(4) C30 C36 1.383(4) C30 C31 1.395(4) C31 C32 1.387(5) C31 H31 0.9300 C32 C33 1.357(5) C32 H32 0.9300 C33 C35 1.373(5) C33 Cl34 1.743(3) C35 C36 1.380(4) C35 H35 0.9300 C36 H36 0.9300 C37 H37A 0.9600 C37 H37B 0.9600 C37 H37C 0.9600 loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_site_symmetry_A C8 H8B N26 0.96 2.53 3.486(4) 173.7 2_666 C37 H37A N19 0.96 2.51 3.454(4) 168.7 2_565 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 C7 C2 C4 N19 -178.7(3) I1 C2 C4 N19 -2.0(5) C7 C2 C4 N5 0.5(3) I1 C2 C4 N5 177.2(2) N19 C4 N5 N6 179.0(3) C2 C4 N5 N6 -0.3(3) N19 C4 N5 C9 2.3(4) C2 C4 N5 C9 -176.9(3) C9 N5 N6 C7 176.4(3) C4 N5 N6 C7 -0.1(3) N5 N6 C7 C2 0.4(4) N5 N6 C7 C8 -178.5(3) C4 C2 C7 N6 -0.6(4) I1 C2 C7 N6 -177.1(2) C4 C2 C7 C8 178.3(3) I1 C2 C7 C8 1.7(5) N6 N5 C9 C17 -178.3(3) C4 N5 C9 C17 -2.2(4) N6 N5 C9 C10 0.6(4) C4 N5 C9 C10 176.8(3) C17 C9 C10 C11 -143.0(3) N5 C9 C10 C11 38.2(4) C17 C9 C10 C16 35.3(5) N5 C9 C10 C16 -143.5(3) C16 C10 C11 C12 0.8(5) C9 C10 C11 C12 179.1(3) C10 C11 C12 C13 0.9(5) C11 C12 C13 C15 -1.3(5) C11 C12 C13 Cl14 176.5(2) C12 C13 C15 C16 0.0(6) Cl14 C13 C15 C16 -177.8(3) C13 C15 C16 C10 1.8(6) C11 C10 C16 C15 -2.1(5) C9 C10 C16 C15 179.5(3) N5 C9 C17 C18 0.8(5) C10 C9 C17 C18 -178.1(3) C9 C17 C18 N19 0.6(6) C17 C18 N19 C4 -0.6(5) C2 C4 N19 C18 178.2(4) N5 C4 N19 C18 -0.8(5) C25 C21 C22 N23 -1.0(4) I20 C21 C22 N23 179.7(2) C25 C21 C22 C37 176.4(3) I20 C21 C22 C37 -2.8(5) C21 C22 N23 N24 0.5(3) C37 C22 N23 N24 -177.1(3) C22 N23 N24 C29 175.4(3) C22 N23 N24 C25 0.1(3) C22 C21 C25 N26 -175.9(3) I20 C21 C25 N26 3.3(5) C22 C21 C25 N24 1.0(3) I20 C21 C25 N24 -179.7(2) N23 N24 C25 N26 176.6(3) C29 N24 C25 N26 1.0(4) N23 N24 C25 C21 -0.8(3) C29 N24 C25 C21 -176.3(3) C21 C25 N26 C27 173.4(3) N24 C25 N26 C27 -3.1(4) C25 N26 C27 C28 2.5(5) N26 C27 C28 C29 0.2(5) C27 C28 C29 N24 -2.3(4) C27 C28 C29 C30 177.2(3) N23 N24 C29 C28 -173.2(3) C25 N24 C29 C28 1.7(4) N23 N24 C29 C30 7.3(4) C25 N24 C29 C30 -177.8(3) C28 C29 C30 C36 -133.8(3) N24 C29 C30 C36 45.6(4) C28 C29 C30 C31 42.4(4) N24 C29 C30 C31 -138.2(3) C36 C30 C31 C32 -1.9(5) C29 C30 C31 C32 -178.2(3) C30 C31 C32 C33 1.4(5) C31 C32 C33 C35 0.1(6) C31 C32 C33 Cl34 179.9(3) C32 C33 C35 C36 -1.0(5) Cl34 C33 C35 C36 179.2(3) C33 C35 C36 C30 0.4(5) C31 C30 C36 C35 1.0(5) C29 C30 C36 C35 177.2(3)