#------------------------------------------------------------------------------ #$Date: 2020-05-23 02:18:12 +0300 (Sat, 23 May 2020) $ #$Revision: 252288 $ #$URL: file:///home/coder/svn-repositories/cod/cif/4/03/84/4038406.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_4038406 loop_ _publ_author_name 'Brittain, William David George' 'Cobb, Steven L.' _publ_section_title ; Protecting Group Controlled Remote Regioselective Electrophilic Aromatic Halogenation Reactions. ; _journal_name_full 'The Journal of organic chemistry' _journal_paper_doi 10.1021/acs.joc.9b03322 _journal_year 2020 _chemical_formula_moiety 'C20 H13 F4 I2 N O2' _chemical_formula_sum 'C20 H13 F4 I2 N O2' _chemical_formula_weight 629.11 _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 geom _atom_sites_solution_primary direct _audit_creation_date 2019-06-04 _audit_creation_method ; Olex2 1.2-beta (compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506) ; _cell_angle_alpha 90 _cell_angle_beta 94.170(2) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 12.3523(3) _cell_length_b 12.7890(3) _cell_length_c 12.8327(3) _cell_measurement_reflns_used 6082 _cell_measurement_temperature 120.0 _cell_measurement_theta_max 32.5080 _cell_measurement_theta_min 2.2550 _cell_volume 2021.86(8) _computing_cell_refinement ; CrysAlisPro, Agilent Technologies, Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET) (compiled Feb 9 2015,16:26:32) ; _computing_data_collection ; CrysAlisPro, Agilent Technologies, Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET) (compiled Feb 9 2015,16:26:32) ; _computing_data_reduction ; CrysAlisPro, Agilent Technologies, Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET) (compiled Feb 9 2015,16:26:32) ; _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 'XS (Sheldrick, 2008)' _diffrn_ambient_temperature 120.0 _diffrn_detector 'CCD area detector' _diffrn_detector_area_resol_mean 16.1511 _diffrn_detector_type Sapphire3 _diffrn_measured_fraction_theta_full 0.999 _diffrn_measured_fraction_theta_max 0.999 _diffrn_measurement_details ; #__ type_ start__ end____ width___ exp.time_ 1 omega 37.00 98.00 1.0000 7.5000 omega____ theta____ kappa____ phi______ frames - 28.9587 57.0000 0.0000 61 #__ type_ start__ end____ width___ exp.time_ 2 omega 30.00 86.00 1.0000 7.5000 omega____ theta____ kappa____ phi______ frames - 28.9587 57.0000 -60.0000 56 #__ type_ start__ end____ width___ exp.time_ 3 omega 64.00 97.00 1.0000 7.5000 omega____ theta____ kappa____ phi______ frames - 28.9587 77.0000 -150.0000 33 #__ type_ start__ end____ width___ exp.time_ 4 omega 12.00 90.00 1.0000 7.5000 omega____ theta____ kappa____ phi______ frames - 28.9587 57.0000 90.0000 78 #__ type_ start__ end____ width___ exp.time_ 5 omega -1.00 97.00 1.0000 7.5000 omega____ theta____ kappa____ phi______ frames - 28.9587 77.0000 120.0000 98 #__ type_ start__ end____ width___ exp.time_ 6 omega 28.00 71.00 1.0000 7.5000 omega____ theta____ kappa____ phi______ frames - 28.9587 -100.0000 -30.0000 43 #__ type_ start__ end____ width___ exp.time_ 7 omega -16.00 71.00 1.0000 7.5000 omega____ theta____ kappa____ phi______ frames - 28.9587 -100.0000 -150.0000 87 ; _diffrn_measurement_device '4-circle diffractometer' _diffrn_measurement_device_type 'Xcalibur, Sapphire3' _diffrn_measurement_method '\w scans' _diffrn_orient_matrix_UB_11 -0.0090851000 _diffrn_orient_matrix_UB_12 0.0473006000 _diffrn_orient_matrix_UB_13 -0.0281390000 _diffrn_orient_matrix_UB_21 -0.0078383000 _diffrn_orient_matrix_UB_22 0.0266819000 _diffrn_orient_matrix_UB_23 0.0473534000 _diffrn_orient_matrix_UB_31 0.0562814000 _diffrn_orient_matrix_UB_32 0.0113597000 _diffrn_orient_matrix_UB_33 0.0061343000 _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength 0.71073 _diffrn_reflns_av_R_equivalents 0.0394 _diffrn_reflns_av_unetI/netI 0.0384 _diffrn_reflns_Laue_measured_fraction_full 0.999 _diffrn_reflns_Laue_measured_fraction_max 0.999 _diffrn_reflns_limit_h_max 17 _diffrn_reflns_limit_h_min -16 _diffrn_reflns_limit_k_max 17 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_l_max 17 _diffrn_reflns_limit_l_min -17 _diffrn_reflns_number 20412 _diffrn_reflns_point_group_measured_fraction_full 0.999 _diffrn_reflns_point_group_measured_fraction_max 0.999 _diffrn_reflns_theta_full 25.242 _diffrn_reflns_theta_max 29.497 _diffrn_reflns_theta_min 2.295 _diffrn_source 'sealed tubeEnhance (Mo) X-ray Source' _diffrn_source_target Mo _diffrn_source_type 'Enhance (Mo) X-ray Source' _exptl_absorpt_coefficient_mu 3.163 _exptl_absorpt_correction_T_max 0.784 _exptl_absorpt_correction_T_min 0.489 _exptl_absorpt_correction_type gaussian _exptl_absorpt_process_details ; CrysAlisPro, Agilent Technologies, Version 1.171.37.35h (release 09-02-2015 CrysAlis171 .NET) (compiled Feb 9 2015,16:26:32) 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 2.067 _exptl_crystal_description prism _exptl_crystal_F_000 1192 _exptl_crystal_size_max 0.38 _exptl_crystal_size_mid 0.17 _exptl_crystal_size_min 0.15 _refine_diff_density_max 0.813 _refine_diff_density_min -0.895 _refine_diff_density_rms 0.122 _refine_ls_extinction_method none _refine_ls_goodness_of_fit_ref 1.024 _refine_ls_hydrogen_treatment constr _refine_ls_matrix_type full _refine_ls_number_parameters 264 _refine_ls_number_reflns 5635 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.024 _refine_ls_R_factor_all 0.0426 _refine_ls_R_factor_gt 0.0294 _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^)+(0.0290P)^2^+0.4130P] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_gt 0.0642 _refine_ls_wR_factor_ref 0.0711 _reflns_Friedel_coverage 0.000 _reflns_number_gt 4454 _reflns_number_total 5635 _reflns_threshold_expression 'I > 2\s(I)' _iucr_refine_instructions_details ; TITL 19srv190 in P21/c #14 REM reset to P21/c #14 CELL 0.71073 12.352342 12.788953 12.832679 90 94.1699 90 ZERR 4 0.000295 0.000333 0.000312 0 0.0022 0 LATT 1 SYMM -X,0.5+Y,0.5-Z SFAC C H F I N O UNIT 80 52 16 8 4 8 EQIV $1 -X,0.5+Y,0.5-Z L.S. 9 PLAN 5 SIZE 0.15 0.17 0.38 TEMP -153.15 HTAB O1 F1_$1 CONF C12 C13 O2 C16 CONF C14 C13 O2 C16 CONF C17 C16 O2 C13 CONF C20 C16 O2 C13 CONF C5 C7 C10 C11 CONF C5 C7 C10 C15 CONF C8 C7 C10 C11 CONF C8 C7 C10 C15 CONF C9 C7 C10 C11 CONF C9 C7 C10 C15 CONF C4 C5 C7 C8 CONF C6 C5 C7 C8 CONF C4 C5 C7 C9 CONF C6 C5 C7 C9 CONF C4 C5 C7 C10 CONF C6 C5 C7 C10 BOND $h fmap 2 53 acta OMIT -2 59 OMIT 0 1 1 OMIT 0 2 0 WGHT 0.029 0.413 FVAR 2.84424 REM REM REM I1 4 -0.39515 0.53278 0.41553 11.00000 0.02065 0.02486 0.02486 = 0.00155 0.00857 0.00492 I2 4 -0.19491 0.52731 -0.00032 11.00000 0.02277 0.02627 0.01642 = 0.00164 -0.00003 -0.00009 F1 3 0.45417 0.27143 0.38299 11.00000 0.02428 0.02414 0.01976 = -0.00043 0.00519 0.00260 F2 3 0.61773 0.13314 0.35370 11.00000 0.03112 0.02596 0.02390 = 0.00595 -0.00076 0.00780 F3 3 0.67089 0.26115 0.03429 11.00000 0.02783 0.03264 0.02933 = 0.00234 0.01441 0.00554 F4 3 0.50169 0.39952 0.04199 11.00000 0.02854 0.02469 0.02331 = 0.00778 0.00357 0.00408 O1 6 -0.36585 0.56926 0.17702 11.00000 0.02003 0.02181 0.02604 = 0.00352 0.00027 0.00687 AFIX 143 H1 2 -0.34227 0.62298 0.14857 11.00000 -1.50000 AFIX 0 O2 6 0.39125 0.41153 0.21832 11.00000 0.01500 0.01694 0.03094 = 0.00357 0.00499 0.00242 N1 5 0.64268 0.19851 0.19448 11.00000 0.01776 0.02017 0.02538 = -0.00095 -0.00040 0.00161 C1 1 -0.27695 0.47812 0.31941 11.00000 0.01482 0.01583 0.02141 = 0.00164 0.00319 0.00019 C2 1 -0.28047 0.50875 0.21462 11.00000 0.01574 0.01377 0.02238 = -0.00011 -0.00128 0.00042 C3 1 -0.19680 0.47495 0.15548 11.00000 0.01565 0.01779 0.01552 = -0.00163 0.00040 -0.00149 C4 1 -0.11501 0.40922 0.19740 11.00000 0.01489 0.01908 0.02120 = -0.00039 0.00437 -0.00017 AFIX 43 H4 2 -0.05939 0.38701 0.15505 11.00000 -1.20000 AFIX 0 C5 1 -0.11378 0.37531 0.30173 11.00000 0.01568 0.01789 0.02159 = 0.00359 0.00178 0.00120 C6 1 -0.19497 0.41183 0.36200 11.00000 0.01980 0.01884 0.02205 = 0.00301 0.00318 0.00127 AFIX 43 H6 2 -0.19482 0.39149 0.43321 11.00000 -1.20000 AFIX 0 C7 1 -0.02919 0.29403 0.34308 11.00000 0.01578 0.02513 0.02319 = 0.00821 0.00261 0.00299 C8 1 -0.01894 0.28994 0.46419 11.00000 0.02386 0.04285 0.02545 = 0.01316 0.00700 0.01057 AFIX 137 H8a 2 -0.00173 0.35985 0.49195 11.00000 -1.50000 H8b 2 0.03911 0.24127 0.48761 11.00000 -1.50000 H8c 2 -0.08771 0.26612 0.48952 11.00000 -1.50000 AFIX 0 C9 1 -0.06918 0.18606 0.30235 11.00000 0.01858 0.02045 0.04463 = 0.00897 0.00738 0.00125 AFIX 137 H9a 2 -0.14100 0.17171 0.32689 11.00000 -1.50000 H9b 2 -0.01806 0.13191 0.32854 11.00000 -1.50000 H9c 2 -0.07386 0.18606 0.22579 11.00000 -1.50000 AFIX 0 C10 1 0.08287 0.32299 0.30549 11.00000 0.01388 0.02223 0.01830 = 0.00341 0.00051 0.00397 C11 1 0.14412 0.25389 0.25017 11.00000 0.01800 0.01765 0.02682 = 0.00052 -0.00037 -0.00080 AFIX 43 H11 2 0.11551 0.18676 0.23235 11.00000 -1.20000 AFIX 0 C12 1 0.24673 0.28125 0.22038 11.00000 0.01744 0.01968 0.02249 = -0.00095 0.00305 0.00274 AFIX 43 H12 2 0.28706 0.23372 0.18152 11.00000 -1.20000 AFIX 0 C13 1 0.28887 0.37755 0.24777 11.00000 0.01359 0.02138 0.01868 = 0.00480 -0.00049 0.00086 C14 1 0.23024 0.45008 0.30133 11.00000 0.01642 0.01597 0.02767 = 0.00072 0.00003 0.00082 AFIX 43 H14 2 0.25918 0.51731 0.31817 11.00000 -1.20000 AFIX 0 C15 1 0.12750 0.42107 0.32961 11.00000 0.01976 0.02174 0.02240 = -0.00151 0.00336 0.00401 AFIX 43 H15 2 0.08654 0.46972 0.36654 11.00000 -1.20000 AFIX 0 C16 1 0.47106 0.33836 0.21172 11.00000 0.01318 0.01545 0.02574 = 0.00037 0.00074 -0.00129 C17 1 0.50380 0.26964 0.29310 11.00000 0.01463 0.01935 0.01780 = -0.00226 0.00175 -0.00145 C18 1 0.58788 0.20110 0.27823 11.00000 0.01738 0.01776 0.01965 = 0.00048 -0.00250 0.00078 C19 1 0.61343 0.26494 0.11936 11.00000 0.01709 0.02078 0.02200 = -0.00129 0.00630 -0.00341 C20 1 0.52861 0.33463 0.12275 11.00000 0.02011 0.01664 0.01884 = 0.00477 -0.00081 -0.00071 HKLF 4 END ; _cod_data_source_file jo9b03322_si_003.cif _cod_data_source_block 8_19srv190 _cod_original_cell_volume 2021.86(9) _cod_database_code 4038406 _shelx_shelxl_version_number 2017/1 _chemical_oxdiff_formula 'C20 H13 N1 O2 F4 I2' _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 0.648 _shelx_estimated_absorpt_t_min 0.379 _reflns_odcompleteness_completeness 99.96 _reflns_odcompleteness_iscentric 1 _reflns_odcompleteness_theta 31.44 _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, All O(H) groups 2.a Aromatic/amide H refined with riding coordinates: C4(H4), C6(H6), C11(H11), C12(H12), C14(H14), C15(H15) 2.b Idealised Me refined as rotating group: C8(H8A,H8B,H8C), C9(H9A,H9B,H9C) 2.c Idealised tetrahedral OH refined with riding coordinates: O1(H1) ; _olex2_submission_special_instructions 'No special instructions were received' 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 I1 I -0.39515(2) 0.53278(2) 0.41553(2) 0.02312(6) Uani 1 1 d . . . . . I2 I -0.19491(2) 0.52730(2) -0.00032(2) 0.02189(6) Uani 1 1 d . . . . . F1 F 0.45417(14) 0.27143(13) 0.38300(13) 0.0225(4) Uani 1 1 d . . . . . F2 F 0.61773(15) 0.13314(14) 0.35370(13) 0.0271(4) Uani 1 1 d . . . . . F3 F 0.67089(15) 0.26115(15) 0.03428(14) 0.0293(4) Uani 1 1 d . . . . . F4 F 0.50169(14) 0.39952(13) 0.04199(13) 0.0254(4) Uani 1 1 d . . . . . O1 O -0.36585(16) 0.56926(16) 0.17701(16) 0.0227(5) Uani 1 1 d . . . . . H1 H -0.342269 0.622978 0.148564 0.034 Uiso 1 1 calc R . . . . O2 O 0.39125(15) 0.41153(15) 0.21832(16) 0.0208(4) Uani 1 1 d . . . . . N1 N 0.6427(2) 0.19851(19) 0.19448(19) 0.0212(5) Uani 1 1 d . . . . . C1 C -0.2770(2) 0.4781(2) 0.3194(2) 0.0173(6) Uani 1 1 d . . . . . C2 C -0.2805(2) 0.5087(2) 0.2146(2) 0.0174(6) Uani 1 1 d . . . . . C3 C -0.1968(2) 0.4750(2) 0.1555(2) 0.0164(6) Uani 1 1 d . . . . . C4 C -0.1150(2) 0.4092(2) 0.1974(2) 0.0182(6) Uani 1 1 d . . . . . H4 H -0.059391 0.387013 0.155047 0.022 Uiso 1 1 calc R . . . . C5 C -0.1138(2) 0.3753(2) 0.3017(2) 0.0184(6) Uani 1 1 d . . . . . C6 C -0.1950(2) 0.4118(2) 0.3620(2) 0.0202(6) Uani 1 1 d . . . . . H6 H -0.194821 0.391495 0.433213 0.024 Uiso 1 1 calc R . . . . C7 C -0.0292(2) 0.2940(2) 0.3431(2) 0.0213(6) Uani 1 1 d . . . . . C8 C -0.0189(3) 0.2899(3) 0.4642(2) 0.0305(8) Uani 1 1 d . . . . . H8A H -0.001733 0.359844 0.491949 0.046 Uiso 1 1 calc GR . . . . H8B H 0.039113 0.241278 0.487600 0.046 Uiso 1 1 calc GR . . . . H8C H -0.087707 0.266108 0.489518 0.046 Uiso 1 1 calc GR . . . . C9 C -0.0692(3) 0.1861(2) 0.3024(3) 0.0276(7) Uani 1 1 d . . . . . H9A H -0.141008 0.171725 0.326878 0.041 Uiso 1 1 calc GR . . . . H9B H -0.018068 0.131916 0.328554 0.041 Uiso 1 1 calc GR . . . . H9C H -0.073848 0.186059 0.225792 0.041 Uiso 1 1 calc GR . . . . C10 C 0.0829(2) 0.3230(2) 0.3055(2) 0.0182(6) Uani 1 1 d . . . . . C11 C 0.1441(2) 0.2539(2) 0.2502(2) 0.0209(6) Uani 1 1 d . . . . . H11 H 0.115513 0.186756 0.232351 0.025 Uiso 1 1 calc R . . . . C12 C 0.2467(2) 0.2813(2) 0.2204(2) 0.0198(6) Uani 1 1 d . . . . . H12 H 0.287062 0.233725 0.181517 0.024 Uiso 1 1 calc R . . . . C13 C 0.2889(2) 0.3776(2) 0.2478(2) 0.0180(6) Uani 1 1 d . . . . . C14 C 0.2302(2) 0.4501(2) 0.3013(2) 0.0201(6) Uani 1 1 d . . . . . H14 H 0.259180 0.517312 0.318167 0.024 Uiso 1 1 calc R . . . . C15 C 0.1275(2) 0.4211(2) 0.3296(2) 0.0212(6) Uani 1 1 d . . . . . H15 H 0.086543 0.469718 0.366539 0.025 Uiso 1 1 calc R . . . . C16 C 0.4711(2) 0.3384(2) 0.2117(2) 0.0181(6) Uani 1 1 d . . . . . C17 C 0.5038(2) 0.2696(2) 0.2931(2) 0.0172(6) Uani 1 1 d . . . . . C18 C 0.5879(2) 0.2011(2) 0.2782(2) 0.0184(6) Uani 1 1 d . . . . . C19 C 0.6134(2) 0.2649(2) 0.1194(2) 0.0197(6) Uani 1 1 d . . . . . C20 C 0.5286(2) 0.3346(2) 0.1228(2) 0.0186(6) 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 I1 0.02065(11) 0.02486(11) 0.02486(11) 0.00155(8) 0.00858(8) 0.00492(8) I2 0.02277(11) 0.02627(11) 0.01642(10) 0.00164(7) -0.00003(7) -0.00009(8) F1 0.0243(9) 0.0241(9) 0.0198(8) -0.0004(7) 0.0052(7) 0.0026(7) F2 0.0311(10) 0.0260(10) 0.0239(9) 0.0059(7) -0.0008(8) 0.0078(8) F3 0.0278(10) 0.0326(11) 0.0293(10) 0.0023(8) 0.0144(8) 0.0055(8) F4 0.0285(10) 0.0247(9) 0.0233(9) 0.0078(7) 0.0036(7) 0.0041(8) O1 0.0200(11) 0.0218(11) 0.0261(11) 0.0035(9) 0.0003(9) 0.0069(9) O2 0.0150(10) 0.0169(10) 0.0309(12) 0.0036(9) 0.0050(8) 0.0024(8) N1 0.0177(12) 0.0202(13) 0.0254(13) -0.0010(10) -0.0004(10) 0.0016(10) C1 0.0148(13) 0.0158(13) 0.0214(14) 0.0016(11) 0.0032(11) 0.0002(11) C2 0.0157(14) 0.0138(13) 0.0224(14) -0.0001(11) -0.0013(11) 0.0004(11) C3 0.0156(13) 0.0178(14) 0.0155(13) -0.0016(10) 0.0004(11) -0.0015(11) C4 0.0149(13) 0.0191(14) 0.0212(14) -0.0004(11) 0.0044(11) -0.0002(11) C5 0.0157(14) 0.0179(14) 0.0216(14) 0.0036(11) 0.0018(11) 0.0012(11) C6 0.0198(14) 0.0188(14) 0.0220(14) 0.0030(12) 0.0032(11) 0.0013(12) C7 0.0158(14) 0.0251(15) 0.0232(15) 0.0082(12) 0.0026(12) 0.0030(12) C8 0.0239(16) 0.043(2) 0.0255(16) 0.0132(14) 0.0070(13) 0.0106(15) C9 0.0186(15) 0.0205(15) 0.045(2) 0.0090(14) 0.0074(14) 0.0013(13) C10 0.0139(13) 0.0222(14) 0.0183(14) 0.0034(11) 0.0005(11) 0.0040(11) C11 0.0180(14) 0.0176(14) 0.0268(16) 0.0005(12) -0.0004(12) -0.0008(12) C12 0.0174(14) 0.0197(14) 0.0225(15) -0.0010(11) 0.0030(11) 0.0027(12) C13 0.0136(13) 0.0214(14) 0.0187(14) 0.0048(11) -0.0005(11) 0.0009(11) C14 0.0164(14) 0.0160(13) 0.0276(16) 0.0007(11) 0.0000(12) 0.0008(11) C15 0.0198(15) 0.0217(15) 0.0224(15) -0.0015(12) 0.0034(12) 0.0040(12) C16 0.0132(13) 0.0154(13) 0.0257(15) 0.0004(11) 0.0007(11) -0.0013(11) C17 0.0146(13) 0.0194(14) 0.0178(13) -0.0023(11) 0.0018(11) -0.0015(11) C18 0.0174(14) 0.0178(14) 0.0196(14) 0.0005(11) -0.0025(11) 0.0008(11) C19 0.0171(14) 0.0208(14) 0.0220(14) -0.0013(12) 0.0063(11) -0.0034(12) C20 0.0201(14) 0.0166(14) 0.0188(14) 0.0048(11) -0.0008(11) -0.0007(11) 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' F F 0.0171 0.0103 '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' N N 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0106 0.0060 '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 _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 -1 -5 1 0.0684 -1.0000 -5.0000 1.0000 -0.2556 -0.0782 -0.1069 5 4 -1 0.0323 5.0000 4.0001 -1.0000 0.1719 0.0202 0.3207 -5 2 2 0.0372 -5.0000 1.9999 2.0000 0.0837 0.1873 -0.2464 0 0 -1 0.1263 -0.0000 0.0000 -1.0000 0.0281 -0.0474 -0.0061 0 0 1 0.1984 0.0000 -0.0000 1.0000 -0.0281 0.0474 0.0061 5 -2 -1 0.0905 5.0000 -1.9999 -1.0000 -0.1119 -0.1399 0.2526 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 O1 H1 109.5 . . ? C16 O2 C13 118.0(2) . . ? C18 N1 C19 117.0(3) . . ? C2 C1 I1 119.8(2) . . ? C2 C1 C6 121.1(3) . . ? C6 C1 I1 119.1(2) . . ? O1 C2 C1 117.9(3) . . ? O1 C2 C3 124.5(3) . . ? C3 C2 C1 117.7(3) . . ? C2 C3 I2 118.5(2) . . ? C4 C3 I2 120.0(2) . . ? C4 C3 C2 121.5(3) . . ? C3 C4 H4 119.6 . . ? C3 C4 C5 120.8(3) . . ? C5 C4 H4 119.6 . . ? C4 C5 C7 119.8(3) . . ? C6 C5 C4 117.9(3) . . ? C6 C5 C7 122.2(3) . . ? C1 C6 H6 119.5 . . ? C5 C6 C1 121.1(3) . . ? C5 C6 H6 119.5 . . ? C5 C7 C8 111.8(3) . . ? C5 C7 C9 107.1(2) . . ? C5 C7 C10 109.4(2) . . ? C9 C7 C8 108.0(3) . . ? C10 C7 C8 108.2(2) . . ? C10 C7 C9 112.4(3) . . ? C7 C8 H8A 109.5 . . ? C7 C8 H8B 109.5 . . ? C7 C8 H8C 109.5 . . ? H8A C8 H8B 109.5 . . ? H8A C8 H8C 109.5 . . ? H8B C8 H8C 109.5 . . ? C7 C9 H9A 109.5 . . ? C7 C9 H9B 109.5 . . ? C7 C9 H9C 109.5 . . ? H9A C9 H9B 109.5 . . ? H9A C9 H9C 109.5 . . ? H9B C9 H9C 109.5 . . ? C11 C10 C7 122.7(3) . . ? C11 C10 C15 117.6(3) . . ? C15 C10 C7 119.7(3) . . ? C10 C11 H11 119.4 . . ? C10 C11 C12 121.3(3) . . ? C12 C11 H11 119.4 . . ? C11 C12 H12 120.3 . . ? C13 C12 C11 119.3(3) . . ? C13 C12 H12 120.3 . . ? C12 C13 O2 122.5(3) . . ? C12 C13 C14 121.6(3) . . ? C14 C13 O2 115.8(3) . . ? C13 C14 H14 121.1 . . ? C13 C14 C15 117.9(3) . . ? C15 C14 H14 121.1 . . ? C10 C15 H15 118.9 . . ? C14 C15 C10 122.2(3) . . ? C14 C15 H15 118.9 . . ? O2 C16 C17 123.6(3) . . ? O2 C16 C20 119.3(3) . . ? C20 C16 C17 117.0(3) . . ? F1 C17 C16 120.2(2) . . ? F1 C17 C18 121.5(3) . . ? C18 C17 C16 118.3(3) . . ? F2 C18 C17 118.9(3) . . ? N1 C18 F2 116.5(2) . . ? N1 C18 C17 124.5(3) . . ? F3 C19 C20 119.7(3) . . ? N1 C19 F3 116.0(3) . . ? N1 C19 C20 124.3(3) . . ? F4 C20 C16 119.8(3) . . ? F4 C20 C19 121.2(3) . . ? C19 C20 C16 118.9(3) . . ? 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 I1 C1 2.099(3) . ? I2 C3 2.110(3) . ? F1 C17 1.345(3) . ? F2 C18 1.333(3) . ? F3 C19 1.346(3) . ? F4 C20 1.350(3) . ? O1 H1 0.8400 . ? O1 C2 1.368(3) . ? O2 C13 1.414(3) . ? O2 C16 1.366(3) . ? N1 C18 1.312(4) . ? N1 C19 1.316(4) . ? C1 C2 1.398(4) . ? C1 C6 1.401(4) . ? C2 C3 1.395(4) . ? C3 C4 1.392(4) . ? C4 H4 0.9500 . ? C4 C5 1.406(4) . ? C5 C6 1.391(4) . ? C5 C7 1.541(4) . ? C6 H6 0.9500 . ? C7 C8 1.551(4) . ? C7 C9 1.545(4) . ? C7 C10 1.544(4) . ? C8 H8A 0.9800 . ? C8 H8B 0.9800 . ? C8 H8C 0.9800 . ? C9 H9A 0.9800 . ? C9 H9B 0.9800 . ? C9 H9C 0.9800 . ? C10 C11 1.391(4) . ? C10 C15 1.396(4) . ? C11 H11 0.9500 . ? C11 C12 1.395(4) . ? C12 H12 0.9500 . ? C12 C13 1.373(4) . ? C13 C14 1.389(4) . ? C14 H14 0.9500 . ? C14 C15 1.395(4) . ? C15 H15 0.9500 . ? C16 C17 1.402(4) . ? C16 C20 1.389(4) . ? C17 C18 1.383(4) . ? C19 C20 1.379(4) . ? 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 _geom_hbond_publ_flag O1 H1 F1 0.84 2.37 2.889(3) 120.9 2 yes 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 C4 C5 C7 C8 163.9(3) . . . . ? C4 C5 C7 C9 -77.9(3) . . . . ? C4 C5 C7 C10 44.1(4) . . . . ? C5 C7 C10 C11 -124.9(3) . . . . ? C5 C7 C10 C15 57.0(3) . . . . ? C6 C5 C7 C8 -20.7(4) . . . . ? C6 C5 C7 C9 97.5(3) . . . . ? C6 C5 C7 C10 -140.5(3) . . . . ? C8 C7 C10 C11 113.1(3) . . . . ? C8 C7 C10 C15 -65.1(3) . . . . ? C9 C7 C10 C11 -6.1(4) . . . . ? C9 C7 C10 C15 175.8(3) . . . . ? C12 C13 O2 C16 -33.6(4) . . . . ? C14 C13 O2 C16 150.0(3) . . . . ? C17 C16 O2 C13 -53.6(4) . . . . ? C20 C16 O2 C13 130.5(3) . . . . ?