# Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2010 data_global _journal_name_full Chem.Commun. _journal_coden_Cambridge 0182 _publ_contact_author_name 'Biradha, Kumar' _publ_contact_author_email kbiradha@chem.iitkgp.ernet.in _publ_section_title ; Assembling Triple Helical Amide-to-Amide Hydrogen Bonded Columns of tris(4-halophenyl)Benzene-1,3,5-tricarboxamides into Porous Materials via Halogen Halogen interactions ; loop_ _publ_author_name K.Biradha L.Rajput V.Chernyshev data_2 _database_code_depnum_ccdc_archive 'CCDC 778387' #TrackingRef 'kb.cif.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C35 H34 I3 N3 O5' _chemical_formula_weight 957.35 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' O O 0.0106 0.0060 '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' _symmetry_cell_setting Trigonal _symmetry_space_group_name_H-M P-31c loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' '-y, -x, -z+1/2' '-x+y, y, -z+1/2' 'x, x-y, -z+1/2' '-x, -y, -z' 'y, -x+y, -z' 'x-y, x, -z' 'y, x, z-1/2' 'x-y, -y, z-1/2' '-x, -x+y, z-1/2' _cell_length_a 22.5852(4) _cell_length_b 22.5852(4) _cell_length_c 7.5192(3) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 3321.62(16) _cell_formula_units_Z 4 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 2045 _cell_measurement_theta_min 1.04 _cell_measurement_theta_max 25.98 _exptl_crystal_description hexagonal _exptl_crystal_colour colorless _exptl_crystal_size_max 0.24 _exptl_crystal_size_mid 0.22 _exptl_crystal_size_min 0.15 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.914 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1856 _exptl_absorpt_coefficient_mu 2.870 _exptl_absorpt_correction_type Empirical _exptl_absorpt_correction_T_min 0.507 _exptl_absorpt_correction_T_max 0.650 _exptl_absorpt_process_details Sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-2 CCD' _diffrn_measurement_method hemisphere _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 38240 _diffrn_reflns_av_R_equivalents 0.0568 _diffrn_reflns_av_sigmaI/netI 0.0185 _diffrn_reflns_limit_h_min -27 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_k_min -27 _diffrn_reflns_limit_k_max 27 _diffrn_reflns_limit_l_min -9 _diffrn_reflns_limit_l_max 9 _diffrn_reflns_theta_min 1.04 _diffrn_reflns_theta_max 25.98 _reflns_number_total 2045 _reflns_number_gt 1829 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.0974P)^2^+45.3703P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 2045 _refine_ls_number_parameters 141 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.0866 _refine_ls_R_factor_gt 0.0772 _refine_ls_wR_factor_ref 0.1928 _refine_ls_wR_factor_gt 0.1840 _refine_ls_goodness_of_fit_ref 0.874 _refine_ls_restrained_S_all 0.874 _refine_ls_shift/su_max 0.001 _refine_ls_shift/su_mean 0.000 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 _atom_site_disorder_assembly _atom_site_disorder_group I1 I 0.24919(4) 0.37044(7) 0.40191(11) 0.0999(5) Uani 1 1 d . . . N11 N 0.5097(3) 0.3406(3) 0.4864(9) 0.0371(14) Uani 1 1 d . . . H11 H 0.5358 0.3601 0.5765 0.044 Uiso 1 1 calc R A 1 C11 C 0.4504(4) 0.3470(4) 0.4653(10) 0.0379(16) Uani 1 1 d . . . C12 C 0.3899(4) 0.2932(5) 0.3977(11) 0.0465(19) Uani 1 1 d . . . H12 H 0.3878 0.2522 0.3670 0.056 Uiso 1 1 calc R . . C13 C 0.3343(4) 0.3002(6) 0.3765(11) 0.054(2) Uani 1 1 d . . . H13 H 0.2948 0.2653 0.3245 0.065 Uiso 1 1 calc R . . C14 C 0.3364(4) 0.3605(6) 0.4334(10) 0.051(2) Uani 1 1 d . . . C15 C 0.3936(5) 0.4126(6) 0.5033(11) 0.053(2) Uani 1 1 d . . . H15 H 0.3947 0.4529 0.5355 0.064 Uiso 1 1 calc R . . C16 C 0.4518(4) 0.4060(4) 0.5272(13) 0.048(2) Uani 1 1 d . . . H16 H 0.4905 0.4403 0.5833 0.058 Uiso 1 1 calc R . . O11A O 0.5762(2) 0.4238(2) 0.7500 0.094(4) Uani 1 2 d S . . O11 O 0.4917(5) 0.2657(5) 0.2552(15) 0.038(2) Uani 0.50 1 d P . . C1 C 0.5274(6) 0.3053(6) 0.3713(16) 0.022(2) Uani 0.50 1 d P . 1 C2 C 0.6007(6) 0.3208(7) 0.3969(15) 0.025(3) Uani 0.50 1 d P . 1 C3 C 0.6540(7) 0.3879(7) 0.3975(16) 0.028(3) Uani 0.50 1 d P . 1 H3 H 0.6455 0.4242 0.3984 0.034 Uiso 0.50 1 calc PR . 1 C1A C 0.5626(7) 0.3733(7) 0.608(2) 0.032(3) Uani 0.50 1 d P . 2 C2A C 0.6142(7) 0.3495(6) 0.6076(15) 0.027(3) Uani 0.50 1 d P . 2 C3A C 0.6843(7) 0.4025(6) 0.6059(18) 0.026(3) Uani 0.50 1 d P . 2 H3A H 0.6955 0.4482 0.6037 0.031 Uiso 0.50 1 calc PR . 2 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 0.0768(6) 0.1974(12) 0.0748(6) 0.0146(6) 0.0017(4) 0.1056(7) N11 0.031(3) 0.035(3) 0.049(4) -0.013(3) -0.005(3) 0.019(3) C11 0.028(3) 0.049(4) 0.041(4) 0.000(3) 0.001(3) 0.023(3) C12 0.031(4) 0.054(5) 0.052(5) -0.016(4) -0.003(3) 0.019(4) C13 0.036(4) 0.079(6) 0.044(5) -0.012(4) -0.010(4) 0.026(4) C14 0.043(5) 0.100(7) 0.034(4) 0.003(4) 0.004(3) 0.053(5) C15 0.053(5) 0.090(7) 0.044(5) 0.001(4) 0.008(4) 0.057(5) C16 0.032(4) 0.050(5) 0.072(6) -0.007(4) -0.007(4) 0.028(4) O11A 0.068(6) 0.068(6) 0.169(14) 0.007(7) 0.007(7) 0.052(6) O11 0.027(5) 0.039(5) 0.054(6) -0.018(6) -0.007(4) 0.021(4) C1 0.015(5) 0.015(5) 0.029(6) 0.011(5) -0.008(4) 0.002(4) C2 0.022(6) 0.041(7) 0.014(5) -0.003(5) -0.003(4) 0.017(5) C3 0.031(7) 0.023(6) 0.024(6) -0.006(5) -0.002(5) 0.007(5) C1A 0.026(6) 0.025(6) 0.043(8) -0.003(6) -0.001(5) 0.012(5) C2A 0.037(7) 0.027(6) 0.018(6) -0.003(5) -0.004(5) 0.018(6) C3A 0.031(6) 0.015(6) 0.036(7) -0.005(5) -0.012(5) 0.013(5) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 C14 2.104(7) . ? N11 C1 1.365(15) . ? N11 C1A 1.387(15) . ? N11 C11 1.426(9) . ? C11 C16 1.398(11) . ? C11 C12 1.394(11) . ? C12 C13 1.353(12) . ? C13 C14 1.405(14) . ? C14 C15 1.346(14) . ? C15 C16 1.406(11) . ? O11A C1A 1.479(15) . ? O11A C1A 1.479(15) 4_666 ? O11 O11 0.900(18) 6 ? O11 C1 1.220(16) . ? O11 C1 1.821(15) 6 ? C1 C2 1.523(16) . ? C1 O11 1.821(15) 6 ? C2 C3 1.385(19) 2_655 ? C2 C3 1.386(18) . ? C3 C2 1.385(19) 3_665 ? C1A C2A 1.507(18) . ? C2A C3A 1.382(18) 2_655 ? C2A C3A 1.430(19) . ? C3A C2A 1.382(18) 3_665 ? 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 C1 N11 C1A 107.7(8) . . ? C1 N11 C11 123.5(7) . . ? C1A N11 C11 128.4(8) . . ? C16 C11 N11 119.1(7) . . ? C16 C11 C12 119.8(7) . . ? N11 C11 C12 120.9(7) . . ? C13 C12 C11 120.3(8) . . ? C12 C13 C14 119.6(8) . . ? C15 C14 C13 121.3(7) . . ? C15 C14 I1 119.4(7) . . ? C13 C14 I1 119.3(7) . . ? C14 C15 C16 119.7(9) . . ? C11 C16 C15 118.9(8) . . ? C1A O11A C1A 121.6(12) . 4_666 ? O11 O11 C1 117.6(15) 6 . ? O11 O11 C1 36.5(10) 6 6 ? C1 O11 C1 117.5(11) . 6 ? O11 C1 N11 127.1(10) . . ? O11 C1 C2 120.1(12) . . ? N11 C1 C2 112.7(10) . . ? O11 C1 O11 26.0(8) . 6 ? N11 C1 O11 142.3(9) . 6 ? C2 C1 O11 100.8(9) . 6 ? C3 C2 C3 122.0(13) 2_655 . ? C3 C2 C1 117.4(11) 2_655 . ? C3 C2 C1 120.1(11) . . ? C2 C3 C2 118.0(13) 3_665 . ? N11 C1A C2A 115.0(11) . . ? N11 C1A O11A 132.7(11) . . ? C2A C1A O11A 112.1(10) . . ? C3A C2A C3A 120.2(12) 2_655 . ? C3A C2A C1A 124.3(12) 2_655 . ? C3A C2A C1A 115.5(11) . . ? C2A C3A C2A 119.8(12) 3_665 . ? _diffrn_measured_fraction_theta_max 0.932 _diffrn_reflns_theta_full 25.98 _diffrn_measured_fraction_theta_full 0.932 _refine_diff_density_max 0.731 _refine_diff_density_min -0.715 _refine_diff_density_rms 0.118 data_3 _database_code_depnum_ccdc_archive 'CCDC 778388' #TrackingRef 'kb.cif.txt' _audit_creation_method manual _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C27 H18 Br3 N3 O3, 1.5(C4 H8 O)' _chemical_formula_sum 'C33 H30 Br3 N3 O4.5' _chemical_formula_weight 780.33 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source Br Br -0.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 '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' 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' _symmetry_cell_setting trigonal _symmetry_space_group_name_H-M 'P 3 1 c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' 'y, x, z+1/2' '-x, -x+y, z+1/2' 'x-y, -y, z+1/2' _cell_length_a 21.9892(18) _cell_length_b 21.9892(18) _cell_length_c 7.3478(5) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.0 _cell_volume 3076.9(4) _cell_formula_units_Z 4 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 738 _cell_measurement_theta_min 2.32 _cell_measurement_theta_max 42.75 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.684 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1560 _exptl_absorpt_coefficient_mu 5.236 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? # The next three fields give the specimen dimensions in mm. The equatorial # plane contains the incident and diffracted beam. _pd_spec_size_axial 15 # perpendicular to # equatorial plane _pd_spec_size_equat 1 # parallel to # scattering vector # in transmission _pd_spec_size_thick 1 # parallel to # scattering vector # in reflection # The next five fields are character fields that describe the specimen. _pd_spec_mounting ; thin layer in the specimen holder of the camera ; _pd_spec_mount_mode transmission # options are 'reflection' # or 'transmission' _pd_spec_shape flat_sheet # options are 'cylinder', # 'flat_sheet' or 'irregular' _pd_char_particle_morphology 'no specific habit' _pd_char_colour colourless # use ICDD colour descriptions # The following three fields describe the preparation of the specimen. # The cooling rate is in K/min. The pressure at which the sample was # prepared is in kPa. The temperature of preparation is in K. _pd_prep_cool_rate ? _pd_prep_pressure 101 _pd_prep_temperature 295(2) _exptl_special_details ; ? ; # This following item is used to identify the equipment used to record the # powder pattern when the diffractogram was measured at a laboratory # other than the authors' home institution, e.g. when neutron or synchrotron # radiation is used. _pd_instr_location ; Dept. of Chemistry, Moscow State University, 119991 Moscow, Russia ; _diffrn_ambient_temperature 295(2) _diffrn_source 'Fine focus X-ray tube' _diffrn_source_target Cu _diffrn_radiation_source 'line-focus sealed tube' _diffrn_radiation_monochromator 'Curved Germanium (111)' _diffrn_measurement_device 'Guinier camera G670' _diffrn_detector_type 'Imaging Plate' _diffrn_reflns_number ? _diffrn_reflns_limit_h_min ? _diffrn_reflns_limit_h_max ? _diffrn_reflns_limit_k_min ? _diffrn_reflns_limit_k_max ? _diffrn_reflns_limit_l_min ? _diffrn_reflns_limit_l_max ? _pd_meas_scan_method cont # options are 'step', 'cont', # 'tof', 'fixed' or # 'disp' (= dispersive) _pd_meas_special_details ; ? ; # The following six items are used for angular dispersive measurements only. _diffrn_radiation_type CuK\a~1~ _diffrn_radiation_wavelength 1.54059 # The following four items give details of the measured (not processed) # powder pattern. Angles are in degrees. _pd_meas_number_of_points 8201 _pd_meas_2theta_range_min 3.00 _pd_meas_2theta_range_max 85.00 _pd_meas_2theta_range_inc 0.01 # The following three items are used for time-of-flight measurements only. _pd_instr_dist_src/spec ? _pd_instr_dist_spec/detc ? _pd_meas_2theta_fixed ? # The following fields are used to identify the programs used. _computing_data_collection 'Huber local program (Huber, 2002)' _computing_cell_refinement 'MRIA (Zlokazov & Chernyshev, 1992)' _computing_data_reduction 'Huber local program' _computing_structure_solution 'simulated annealing (Zhukov et al., 2001)' _computing_structure_refinement MRIA _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material ; MRIA, SHELXL97 (Sheldrick, 1997) ; #============================================================================== # 8. REFINEMENT DATA # Use the next field to give any special details about the fitting of the # powder pattern. _pd_proc_ls_special_details ; ? ; # The next three items are given as text _pd_proc_ls_profile_function 'split-type pseudo-Voigt (Toraya, 1986)' _pd_proc_ls_pref_orient_corr none _pd_proc_ls_background_function 'Chebyshev polynomial up to the 5th order' _pd_proc_ls_prof_R_factor 0.0144 _pd_proc_ls_prof_wR_factor 0.0187 _pd_proc_ls_prof_wR_expected 0.0099 _refine_special_details ; ? ; _refine_ls_R_I_factor 0.0667 _refine_ls_structure_factor_coef Inet _refine_ls_matrix_type fullcycle _refine_ls_weighting_scheme sigma _refine_ls_hydrogen_treatment noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_parameters 151 _refine_ls_number_restraints 80 _refine_ls_number_constraints 36 # The following item is the same as CHI, the square root of 'CHI squared' _refine_ls_goodness_of_fit_all 1.888 _refine_ls_restrained_S_all ? _refine_ls_restrained_S_obs ? _refine_ls_shift/su_max .005 _refine_ls_shift/su_mean .002 # The following four items apply to angular dispersive measurements. # 2theta minimum, maximum and increment (in degrees) are for the # intensities used in the refinement. _pd_proc_2theta_range_min 3.00 _pd_proc_2theta_range_max 85.00 _pd_proc_2theta_range_inc 0.01 _pd_proc_wavelength 1.54059 _pd_block_diffractogram_id Bromo_pattern # The id used for the block # containing the powder # pattern profile (section 11). # Give appropriate details in the next two text fields. _pd_proc_info_excluded_regions none _pd_proc_info_data_reduction ? #============================================================================== # 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS 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 _atom_site_disorder_assembly _atom_site_disorder_group Br1 Br -0.1227(1) 0.6276(1) 0.4630(5) 0.045(3) Uiso 1 1 d . . . O1 O 0.2325(5) 0.7545(5) 0.5924(15) 0.056(7) Uiso 1 1 d . . . N1 N 0.1676(6) 0.6570(6) 0.4018(18) 0.056(7) Uiso 1 1 d . . . H1 H 0.1752 0.6321 0.3246 0.067 Uiso 1 1 calc . . . C1 C 0.2243(7) 0.7036(8) 0.5013(18) 0.056(7) Uiso 1 1 d . . . C2 C 0.0980(8) 0.6444(7) 0.4095(21) 0.056(7) Uiso 1 1 d . . . C3 C 0.0374(6) 0.5825(8) 0.3580(17) 0.056(7) Uiso 1 1 d . . . H3 H 0.0406 0.5442 0.3170 0.067 Uiso 1 1 calc . . . C4 C -0.0280(8) 0.5784(8) 0.3684(22) 0.056(7) Uiso 1 1 d . . . H4 H -0.0683 0.5380 0.3306 0.067 Uiso 1 1 calc . . . C5 C -0.0324(7) 0.6353(7) 0.4359(19) 0.056(7) Uiso 1 1 d . . . C6 C 0.0276(8) 0.6979(8) 0.4862(23) 0.056(7) Uiso 1 1 d . . . H6 H 0.0245 0.7369 0.5207 0.067 Uiso 1 1 calc . . . C7 C 0.0919(8) 0.7004(7) 0.4834(21) 0.056(7) Uiso 1 1 d . . . H7 H 0.1314 0.7393 0.5308 0.067 Uiso 1 1 calc . . . C8 C 0.2825(7) 0.6865(7) 0.5013(18) 0.056(7) Uiso 1 1 d . . . C9 C 0.2625(8) 0.6149(8) 0.5013(18) 0.056(7) Uiso 1 1 d . . . H9 H 0.2152 0.5806 0.5013 0.067 Uiso 1 1 calc . . . Br2 Br 0.3555(1) 1.1172(1) -0.2225(4) 0.053(3) Uiso 1 1 d . . . O2 O 0.4216(6) 0.8559(5) 0.0939(19) 0.059(7) Uiso 1 1 d . . . N2 N 0.3299(6) 0.8305(6) -0.1025(21) 0.059(7) Uiso 1 1 d . . . H2 H 0.2959 0.7968 -0.1611 0.071 Uiso 1 1 calc . . . C10 C 0.3711(7) 0.8135(9) 0.0000(23) 0.059(7) Uiso 1 1 d . . . C11 C 0.3376(8) 0.8981(8) -0.1221(20) 0.059(7) Uiso 1 1 d . . . C12 C 0.3981(9) 0.9596(7) -0.0659(22) 0.059(7) Uiso 1 1 d . . . H12 H 0.4347 0.9570 -0.0099 0.071 Uiso 1 1 calc . . . C13 C 0.4029(8) 1.0245(8) -0.0945(19) 0.059(7) Uiso 1 1 d . . . H13 H 0.4424 1.0655 -0.0556 0.071 Uiso 1 1 calc . . . C14 C 0.3482(8) 1.0277(8) -0.1820(24) 0.059(7) Uiso 1 1 d . . . C15 C 0.2860(9) 0.9667(8) -0.2293(23) 0.059(7) Uiso 1 1 d . . . H15 H 0.2477 0.9692 -0.2739 0.071 Uiso 1 1 calc . . . C16 C 0.2826(8) 0.9021(7) -0.2081(19) 0.059(7) Uiso 1 1 d . . . H16 H 0.2438 0.8614 -0.2510 0.071 Uiso 1 1 calc . . . C17 C 0.3505(8) 0.7372(8) 0.0000(23) 0.059(7) Uiso 1 1 d . . . C18 C 0.4039(7) 0.7201(7) 0.0000(23) 0.059(7) Uiso 1 1 d . . . H18 H 0.4507 0.7555 0.0000 0.067 Uiso 1 1 calc . . . O1A O 0.1317(16) 0.1611(16) 0.1706(53) 0.18(2) Uiso 0.50 1 d P . . C1A C 0.0774(21) 0.0984(22) 0.0922(58) 0.18(2) Uiso 0.50 1 d P . . H1AA H 0.0687 0.1059 -0.0331 0.221 Uiso 0.50 1 calc P . . H1AB H 0.0342 0.0803 0.1611 0.221 Uiso 0.50 1 calc P . . C2A C 0.1078(23) 0.0482(24) 0.1035(60) 0.18(2) Uiso 0.50 1 d P . . H2AA H 0.0847 0.0144 0.2004 0.221 Uiso 0.50 1 calc P . . H2AB H 0.0993 0.0227 -0.0101 0.221 Uiso 0.50 1 calc P . . C3A C 0.1835(22) 0.0887(23) 0.1386(53) 0.18(2) Uiso 0.50 1 d P . . H3AA H 0.2102 0.1016 0.0264 0.221 Uiso 0.50 1 calc P . . H3AB H 0.1986 0.0630 0.2156 0.221 Uiso 0.50 1 calc P . . C4A C 0.1903(24) 0.1516(23) 0.2338(59) 0.18(2) Uiso 0.50 1 d P . . H4AA H 0.1876 0.1445 0.3645 0.221 Uiso 0.50 1 calc P . . H4AB H 0.2350 0.1927 0.2047 0.221 Uiso 0.50 1 calc P . . O1B O -0.0087(18) 0.1456(13) -0.0921(53) 0.18(2) Uiso 0.50 1 d P . . C1B C -0.0539(23) 0.1134(23) 0.0593(62) 0.18(2) Uiso 0.50 1 d P . . H1BA H -0.0946 0.0690 0.0254 0.221 Uiso 0.50 1 calc P . . H1BB H -0.0695 0.1439 0.1111 0.221 Uiso 0.50 1 calc P . . C2B C -0.0058(25) 0.1022(21) 0.1932(65) 0.18(2) Uiso 0.50 1 d P . . H2BA H -0.0133 0.1133 0.3164 0.221 Uiso 0.50 1 calc P . . H2BB H -0.0174 0.0535 0.1907 0.221 Uiso 0.50 1 calc P . . C3B C 0.0679(21) 0.1477(23) 0.1416(55) 0.18(2) Uiso 0.50 1 d P . . H3BA H 0.0956 0.1254 0.1664 0.221 Uiso 0.50 1 calc P . . H3BB H 0.0885 0.1925 0.2047 0.221 Uiso 0.50 1 calc P . . C4B C 0.0621(23) 0.1564(22) -0.0572(58) 0.18(2) Uiso 0.50 1 d P . . H4BA H 0.0975 0.2032 -0.0955 0.221 Uiso 0.50 1 calc P . . H4BB H 0.0689 0.1224 -0.1246 0.221 Uiso 0.50 1 calc P . . 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 Br1 C5 1.917(17) . ? Br2 C14 1.916(16) . ? O1 C1 1.238(18) . ? O2 C10 1.24(2) . ? N1 C1 1.36(2) . ? N1 C2 1.41(2) . ? N1 H1 0.86 . ? N2 C11 1.42(2) . ? N2 C10 1.36(2) . ? N2 H2 0.86 . ? C1 C8 1.50(2) . ? C2 C3 1.40(2) . ? C2 C7 1.41(2) . ? C3 C4 1.40(3) . ? C4 C5 1.39(2) . ? C5 C6 1.40(2) . ? C6 C7 1.39(3) . ? C8 C9 1.38(3) 3_565 ? C8 C9 1.41(2) . ? C3 H3 0.93 . ? C4 H4 0.93 . ? C6 H6 0.93 . ? C7 H7 0.93 . ? C9 H9 0.93 . ? C10 C17 1.50(2) . ? C11 C16 1.41(3) . ? C11 C12 1.40(2) . ? C12 C13 1.39(2) . ? C13 C14 1.40(3) . ? C14 C15 1.40(2) . ? C15 C16 1.39(2) . ? C17 C18 1.40(3) 2_665 ? C17 C18 1.40(3) . ? C12 H12 0.93 . ? C13 H13 0.93 . ? C15 H15 0.93 . ? C16 H16 0.93 . ? C18 H18 0.93 . ? O1A C4A 1.47(6) . ? O1A C1A 1.43(5) . ? O1B C1B 1.42(6) . ? O1B C4B 1.48(6) . ? C1B C2B 1.53(7) . ? C2A C3A 1.47(7) . ? C2B C3B 1.47(6) . ? C3A C4A 1.50(6) . ? C3B C4B 1.49(6) . ? C1A H1AA 0.97 . ? C1A H1AB 0.96 . ? C1B H1BA 0.96 . ? C1B H1BB 0.97 . ? C2A H2AB 0.97 . ? C2B H2BA 0.97 . ? C2B H2BB 0.97 . ? C3A H3AA 0.97 . ? C3A H3AB 0.96 . ? C3B H3BA 0.97 . ? C3B H3BB 0.97 . ? C4A H4AA 0.97 . ? C4A H4AB 0.97 . ? C4B H4BA 0.97 . ? C4B H4BB 0.96 . ? 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 C1 N1 C2 128.1(13) . . ? C1 N1 H1 116 . . ? C2 N1 H1 116 . . ? C10 N2 C11 126.7(14) . . ? C11 N2 H2 117 . . ? C10 N2 H2 117 . . ? N1 C1 C8 112.6(13) . . ? O1 C1 C8 118.0(14) . . ? O1 C1 N1 129.4(16) . . ? C3 C2 C7 119.5(16) . . ? N1 C2 C3 126.1(14) . . ? N1 C2 C7 114.3(13) . . ? C2 C3 C4 119.8(14) . . ? C3 C4 C5 119.5(15) . . ? Br1 C5 C6 119.0(12) . . ? Br1 C5 C4 119.4(12) . . ? C4 C5 C6 121.5(16) . . ? C5 C6 C7 118.4(15) . . ? C2 C7 C6 120.8(14) . . ? C1 C8 C9 116.8(14) . . ? C9 C8 C9 120.6(17) . 3_565 ? C1 C8 C9 122.6(14) . 3_565 ? C8 C9 C8 119.4(16) . 2_665 ? C2 C3 H3 120 . . ? C4 C3 H3 120 . . ? C5 C4 H4 120 . . ? C3 C4 H4 120 . . ? C5 C6 H6 120 . . ? C7 C6 H6 120 . . ? C6 C7 H7 120 . . ? C2 C7 H7 120 . . ? C8 C9 H9 120 . . ? O2 C10 N2 124.5(15) . . ? O2 C10 C17 119.7(15) . . ? N2 C10 C17 115.8(14) . . ? N2 C11 C16 117.2(14) . . ? N2 C11 C12 122.6(16) . . ? C12 C11 C16 120.2(15) . . ? C11 C12 C13 119.5(18) . . ? C12 C13 C14 119.7(15) . . ? C13 C14 C15 121.3(15) . . ? Br2 C14 C13 119.4(12) . . ? Br2 C14 C15 119.1(14) . . ? C14 C15 C16 118.6(18) . . ? C11 C16 C15 120.3(14) . . ? C10 C17 C18 118.3(15) . . ? C10 C17 C18 121.6(17) . 2_665 ? C18 C17 C18 120.1(15) . 2_665 ? C17 C18 C17 119.9(16) . 3_565 ? C11 C12 H12 120 . . ? C13 C12 H12 120 . . ? C12 C13 H13 120 . . ? C14 C13 H13 120 . . ? C14 C15 H15 120 . . ? C16 C15 H15 120 . . ? C11 C16 H16 120 . . ? C15 C16 H16 120 . . ? C17 C18 H18 120 . . ? O1A C1A C2A 102(4) . . ? O1B C1B C2B 102(4) . . ? C1A C2A C3A 110(3) . . ? C1B C2B C3B 110(4) . . ? C2A C3A C4A 101(4) . . ? C2B C3B C4B 101(4) . . ? O1A C4A C3A 107(4) . . ? O1B C4B C3B 108(4) . . ? C1A O1A C4A 111(3) . . ? C1B O1B C4B 111(4) . . ? O1A C1A H1AA 111 . . ? O1A C1A H1AB 111 . . ? C2A C1A H1AA 111 . . ? C2A C1A H1AB 111 . . ? H1AA C1A H1AB 111 . . ? O1B C1B H1BA 111 . . ? O1B C1B H1BB 111 . . ? C2B C1B H1BA 111 . . ? C2B C1B H1BB 111 . . ? H1BA C1B H1BB 109 . . ? C1A C2A H2AB 109 . . ? C3A C2A H2AB 110 . . ? C1B C2B H2BA 110 . . ? C1B C2B H2BB 110 . . ? C3B C2B H2BA 109 . . ? C3B C2B H2BB 110 . . ? H3BA C3B H3BB 110 . . ? O1A C4A H4AA 110 . . ? O1A C4A H4AB 111 . . ? C3A C4A H4AA 109 . . ? C3A C4A H4AB 109 . . ? H4AA C4A H4AB 109 . . ? O1B C4B H4BA 109 . . ? O1B C4B H4BB 110 . . ? C3B C4B H4BA 110 . . ? C3B C4B H4BB 111 . . ? H4BA C4B H4BB 108 . . ? H2BA C2B H2BB 108 . . ? C2A C3A H3AA 111 . . ? C2A C3A H3AB 111 . . ? C4A C3A H3AA 111 . . ? C4A C3A H3AB 111 . . ? H3AA C3A H3AB 110 . . ? C2B C3B H3BA 111 . . ? C2B C3B H3BB 111 . . ? C4B C3B H3BA 111 . . ? C4B C3B H3BB 111 . . ? 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 N1 H1 O2 0.86 2.12 2.895(19) 150 2_665 N2 H2 O1 0.86 2.19 2.974(18) 151 1_554 _refine_diff_density_max 0.65 _refine_diff_density_min -0.54 _refine_diff_density_rms 0.33 data_4 _database_code_depnum_ccdc_archive 'CCDC 778389' #TrackingRef 'kb.cif.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety 'C27 H18 Cl3 N3 O3, 1.5(C4 H8 O)' _chemical_formula_sum 'C33 H30 Cl3 N3 O4.5' _chemical_formula_weight 646.9 loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source Cl Cl 0.3639 0.7018 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O 0.0492 0.0322 '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' 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' _symmetry_cell_setting trigonal _symmetry_space_group_name_H-M 'P 3 1 c' loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-y, x-y, z' '-x+y, -x, z' 'y, x, z+1/2' '-x, -x+y, z+1/2' 'x-y, -y, z+1/2' _cell_length_a 21.6250(17) _cell_length_b 21.6250(17) _cell_length_c 7.3012(6) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 120.00 _cell_volume 2956.9(4) _cell_formula_units_Z 4 _cell_measurement_temperature 295(2) _cell_measurement_reflns_used 706 _cell_measurement_theta_min 2.87 _cell_measurement_theta_max 42.75 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.453 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 1344 _exptl_absorpt_coefficient_mu 3.192 _exptl_absorpt_correction_type ? _exptl_absorpt_correction_T_min ? _exptl_absorpt_correction_T_max ? _exptl_absorpt_process_details ? # The next three fields give the specimen dimensions in mm. The equatorial # plane contains the incident and diffracted beam. _pd_spec_size_axial 15 # perpendicular to # equatorial plane _pd_spec_size_equat 1 # parallel to # scattering vector # in transmission _pd_spec_size_thick 1 # parallel to # scattering vector # in reflection # The next five fields are character fields that describe the specimen. _pd_spec_mounting ; thin layer in the specimen holder of the camera ; _pd_spec_mount_mode transmission # options are 'reflection' # or 'transmission' _pd_spec_shape flat_sheet # options are 'cylinder', # 'flat_sheet' or 'irregular' _pd_char_particle_morphology 'no specific habit' _pd_char_colour colourless # use ICDD colour descriptions # The following three fields describe the preparation of the specimen. # The cooling rate is in K/min. The pressure at which the sample was # prepared is in kPa. The temperature of preparation is in K. _pd_prep_cool_rate ? _pd_prep_pressure 101 _pd_prep_temperature 295(2) _exptl_special_details ; ? ; # This following item is used to identify the equipment used to record the # powder pattern when the diffractogram was measured at a laboratory # other than the authors' home institution, e.g. when neutron or synchrotron # radiation is used. _pd_instr_location ; Dept. of Chemistry, Moscow State University, 119991 Moscow, Russia ; _diffrn_ambient_temperature 295(2) _diffrn_source 'Fine focus X-ray tube' _diffrn_source_target Cu _diffrn_radiation_source 'line-focus sealed tube' _diffrn_radiation_monochromator 'Curved Germanium (111)' _diffrn_measurement_device 'Guinier camera G670' _diffrn_detector_type 'Imaging Plate' _diffrn_reflns_number ? _diffrn_reflns_limit_h_min ? _diffrn_reflns_limit_h_max ? _diffrn_reflns_limit_k_min ? _diffrn_reflns_limit_k_max ? _diffrn_reflns_limit_l_min ? _diffrn_reflns_limit_l_max ? _pd_meas_scan_method cont # options are 'step', 'cont', # 'tof', 'fixed' or # 'disp' (= dispersive) _pd_meas_special_details ; ? ; # The following six items are used for angular dispersive measurements only. _diffrn_radiation_type CuK\a~1~ _diffrn_radiation_wavelength 1.54059 # The following four items give details of the measured (not processed) # powder pattern. Angles are in degrees. _pd_meas_number_of_points 8201 _pd_meas_2theta_range_min 3.00 _pd_meas_2theta_range_max 85.00 _pd_meas_2theta_range_inc 0.01 # The following three items are used for time-of-flight measurements only. _pd_instr_dist_src/spec ? _pd_instr_dist_spec/detc ? _pd_meas_2theta_fixed ? # The following fields are used to identify the programs used. _computing_data_collection 'Huber local program (Huber, 2002)' _computing_cell_refinement 'MRIA (Zlokazov & Chernyshev, 1992)' _computing_data_reduction 'Huber local program' _computing_structure_solution 'simulated annealing (Zhukov et al., 2001)' _computing_structure_refinement MRIA _computing_molecular_graphics 'PLATON (Spek, 2003)' _computing_publication_material ; MRIA, SHELXL97 (Sheldrick, 1997) ; #============================================================================== # 8. REFINEMENT DATA # Use the next field to give any special details about the fitting of the # powder pattern. _pd_proc_ls_special_details ; ? ; # The next three items are given as text _pd_proc_ls_profile_function 'split-type pseudo-Voigt (Toraya, 1986)' _pd_proc_ls_pref_orient_corr none _pd_proc_ls_background_function 'Chebyshev polynomial up to the 5th order' _pd_proc_ls_prof_R_factor 0.0184 _pd_proc_ls_prof_wR_factor 0.0237 _pd_proc_ls_prof_wR_expected 0.0112 _refine_special_details ; ? ; _refine_ls_R_I_factor 0.0704 _refine_ls_structure_factor_coef Inet _refine_ls_matrix_type fullcycle _refine_ls_weighting_scheme sigma _refine_ls_hydrogen_treatment noref _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_parameters 151 _refine_ls_number_restraints 80 _refine_ls_number_constraints 36 # The following item is the same as CHI, the square root of 'CHI squared' _refine_ls_goodness_of_fit_all 2.123 _refine_ls_restrained_S_all ? _refine_ls_restrained_S_obs ? _refine_ls_shift/su_max .003 _refine_ls_shift/su_mean .001 # The following four items apply to angular dispersive measurements. # 2theta minimum, maximum and increment (in degrees) are for the # intensities used in the refinement. _pd_proc_2theta_range_min 3.00 _pd_proc_2theta_range_max 85.00 _pd_proc_2theta_range_inc 0.01 _pd_proc_wavelength 1.54059 _pd_block_diffractogram_id Chloro_pattern # The id used for the block # containing the powder # pattern profile (section 11). # Give appropriate details in the next two text fields. _pd_proc_info_excluded_regions none _pd_proc_info_data_reduction ? #============================================================================== # 9. ATOMIC COORDINATES AND DISPLACEMENT PARAMETERS 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 _atom_site_disorder_assembly _atom_site_disorder_group Cl1 Cl -0.12610(15) 0.62440(15) 0.4657(4) 0.054(3) Uiso 1 1 d . . . O1 O 0.2300(3) 0.7564(3) 0.5957(10) 0.061(5) Uiso 1 1 d . . . N1 N 0.1647(4) 0.6608(4) 0.4022(13) 0.061(5) Uiso 1 1 d . . . H1 H 0.1721 0.6378 0.3169 0.073 Uiso 1 1 calc . . . C1 C 0.2229(5) 0.7043(5) 0.5074(17) 0.061(5) Uiso 1 1 d . . . C2 C 0.0944(6) 0.6485(5) 0.4145(18) 0.061(5) Uiso 1 1 d . . . C3 C 0.0337(6) 0.5837(5) 0.3665(17) 0.061(5) Uiso 1 1 d . . . H3 H 0.0387 0.5456 0.3263 0.073 Uiso 1 1 calc . . . C4 C -0.0342(6) 0.5762(6) 0.3788(16) 0.061(5) Uiso 1 1 d . . . H4 H -0.0744 0.5333 0.3470 0.073 Uiso 1 1 calc . . . C5 C -0.0413(5) 0.6336(5) 0.4391(17) 0.061(5) Uiso 1 1 d . . . C6 C 0.0184(6) 0.6979(6) 0.4907(18) 0.061(5) Uiso 1 1 d . . . H6 H 0.0133 0.7361 0.5286 0.073 Uiso 1 1 calc . . . C7 C 0.0857(6) 0.7043(5) 0.4849(17) 0.061(5) Uiso 1 1 d . . . H7 H 0.1252 0.7457 0.5278 0.073 Uiso 1 1 calc . . . C8 C 0.2811(5) 0.6860(5) 0.5074(18) 0.061(5) Uiso 1 1 d . . . C9 C 0.2611(6) 0.6132(6) 0.5074(18) 0.061(5) Uiso 1 1 d . . . H9 H 0.2132 0.5780 0.5074 0.073 Uiso 1 1 calc . . . Cl2 Cl 0.35060(14) 1.11620(12) -0.2133(4) 0.051(3) Uiso 1 1 d . . . O2 O 0.4220(4) 0.8584(3) 0.1042(12) 0.057(5) Uiso 1 1 d . . . N2 N 0.3346(4) 0.8351(4) -0.1103(13) 0.057(5) Uiso 1 1 d . . . H2 H 0.3037 0.8021 -0.1803 0.068 Uiso 1 1 calc . . . C10 C 0.3733(5) 0.8160(5) 0.0015(18) 0.057(5) Uiso 1 1 d . . . C11 C 0.3397(6) 0.9028(6) -0.1236(16) 0.057(5) Uiso 1 1 d . . . C12 C 0.4010(5) 0.9667(5) -0.0717(16) 0.057(5) Uiso 1 1 d . . . H12 H 0.4397 0.9654 -0.0205 0.068 Uiso 1 1 calc . . . C13 C 0.4038(5) 1.0320(5) -0.0970(15) 0.057(5) Uiso 1 1 d . . . H13 H 0.4439 1.0742 -0.0602 0.068 Uiso 1 1 calc . . . C14 C 0.3462(5) 1.0337(5) -0.1779(16) 0.057(5) Uiso 1 1 d . . . C15 C 0.2835(6) 0.9706(5) -0.2201(18) 0.057(5) Uiso 1 1 d . . . H15 H 0.2442 0.9721 -0.2661 0.068 Uiso 1 1 calc . . . C16 C 0.2804(5) 0.9053(5) -0.1926(17) 0.057(5) Uiso 1 1 d . . . H16 H 0.2387 0.8630 -0.2202 0.068 Uiso 1 1 calc . . . C17 C 0.3513(6) 0.7387(5) 0.0015(18) 0.057(5) Uiso 1 1 d . . . C18 C 0.4054(5) 0.7205(6) 0.0015(18) 0.057(5) Uiso 1 1 d . . . H18 H 0.4531 0.7562 0.0015 0.068 Uiso 1 1 calc . . . O1A O 0.0082(17) 0.0877(15) -0.198(6) 0.27(2) Uiso 0.50 1 d P . . C1A C -0.0364(21) 0.1090(22) -0.1073(85) 0.27(2) Uiso 0.50 1 d P . . H1A1 H -0.0818 0.0680 -0.0734 0.320 Uiso 0.50 1 calc P . . H1A2 H -0.0451 0.1406 -0.1838 0.320 Uiso 0.50 1 calc P . . C2A C 0.0077(22) 0.1483(17) 0.0634(77) 0.27(2) Uiso 0.50 1 d P . . H2A1 H 0.0230 0.1987 0.0543 0.320 Uiso 0.50 1 calc P . . H2A2 H -0.0218 0.1295 0.1719 0.320 Uiso 0.50 1 calc P . . C3A C 0.0702(25) 0.1395(23) 0.0805(76) 0.27(2) Uiso 0.50 1 d P . . H3A1 H 0.0611 0.1007 0.1631 0.321 Uiso 0.50 1 calc P . . H3A2 H 0.1116 0.1831 0.1231 0.321 Uiso 0.50 1 calc P . . C4A C 0.0800(21) 0.1225(23) -0.1125(68) 0.27(2) Uiso 0.50 1 d P . . H4A1 H 0.1124 0.1658 -0.1781 0.321 Uiso 0.50 1 calc P . . H4A2 H 0.0994 0.0906 -0.1140 0.321 Uiso 0.50 1 calc P . . O1B O 0.2061(12) 0.1856(14) 0.2716(64) 0.27(2) Uiso 0.50 1 d P . . C1B C 0.1514(23) 0.1454(21) 0.1392(80) 0.27(2) Uiso 0.50 1 d P . . H1B1 H 0.1674 0.1625 0.0158 0.320 Uiso 0.50 1 calc P . . H1B2 H 0.1083 0.1472 0.1646 0.320 Uiso 0.50 1 calc P . . C2B C 0.1396(24) 0.0695(26) 0.1674(81) 0.27(2) Uiso 0.50 1 d P . . H2B1 H 0.0888 0.0357 0.1733 0.321 Uiso 0.50 1 calc P . . H2B2 H 0.1590 0.0569 0.0634 0.321 Uiso 0.50 1 calc P . . C3B C 0.1735(20) 0.0647(21) 0.3341(79) 0.27(2) Uiso 0.50 1 d P . . H3B1 H 0.2127 0.0564 0.3067 0.321 Uiso 0.50 1 calc P . . H3B2 H 0.1395 0.0267 0.4124 0.321 Uiso 0.50 1 calc P . . C4B C 0.1999(23) 0.1357(23) 0.4216(78) 0.27(2) Uiso 0.50 1 d P . . H4B1 H 0.2460 0.1519 0.4786 0.321 Uiso 0.50 1 calc P . . H4B2 H 0.1666 0.1332 0.5145 0.321 Uiso 0.50 1 calc P . . _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 Cl1 C5 1.754(12) . ? O1 C1 1.239(14) . ? N1 C1 1.369(12) . ? N1 C2 1.409(16) . ? N1 H1 0.86 . ? C1 C8 1.496(19) . ? C2 C3 1.404(13) . ? C2 C7 1.408(19) . ? C3 C4 1.397(19) . ? C3 H3 0.93 . ? C4 C5 1.396(19) . ? C4 H4 0.93 . ? C5 C6 1.395(13) . ? C6 C7 1.39(2) . ? C6 H6 0.93 . ? C7 H7 0.93 . ? C8 C9 1.382(17) 3_565 ? C8 C9 1.409(17) . ? C9 C8 1.382(17) 2_665 ? C9 H9 0.93 . ? Cl2 C14 1.758(12) . ? O2 C10 1.244(13) . ? N2 C10 1.372(17) . ? N2 C11 1.416(17) . ? N2 H2 0.86 . ? C10 C17 1.492(16) . ? C11 C16 1.403(18) . ? C11 C12 1.407(12) . ? C12 C13 1.395(17) . ? C12 H12 0.93 . ? C13 C14 1.395(18) . ? C13 H13 0.93 . ? C14 C15 1.395(12) . ? C15 C16 1.394(17) . ? C15 H15 0.93 . ? C16 H16 0.93 . ? C17 C18 1.399(15) 2_665 ? C17 C18 1.41(2) . ? C18 C17 1.399(15) 3_565 ? C18 H18 0.93 . ? O1A C1A 1.42(7) . ? O1A C4A 1.48(6) . ? C1A C2A 1.54(8) . ? C1A H1A1 0.9703 . ? C1A H1A2 0.9795 . ? C2A C3A 1.46(9) . ? C2A H2A1 0.97 . ? C2A H2A2 0.97 . ? C3A C4A 1.50(9) . ? C3A H3A1 0.97 . ? C3A H3A2 0.97 . ? C4A H4A1 0.97 . ? C4A H4A2 0.97 . ? O1B C1B 1.44(7) . ? O1B C4B 1.50(7) . ? C1B C2B 1.54(8) . ? C1B H1B1 0.97 . ? C1B H1B2 0.97 . ? C2B C3B 1.45(9) . ? C2B H2B1 0.97 . ? C2B H2B2 0.97 . ? C3B C4B 1.49(7) . ? C3B H3B1 0.97 . ? C3B H3B2 0.97 . ? C4B H4B1 0.97 . ? C4B H4B2 0.97 . ? 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 C1 N1 C2 128.9(11) . . ? C1 N1 H1 115.5 . . ? C2 N1 H1 115.5 . . ? O1 C1 N1 124.8(12) . . ? O1 C1 C8 120.1(9) . . ? N1 C1 C8 115.1(11) . . ? C3 C2 C7 119.2(12) . . ? C3 C2 N1 123.7(12) . . ? C7 C2 N1 117.1(8) . . ? C4 C3 C2 120.2(12) . . ? C4 C3 H3 119.9 . . ? C2 C3 H3 119.9 . . ? C5 C4 C3 119.6(9) . . ? C5 C4 H4 120.2 . . ? C3 C4 H4 120.2 . . ? C6 C5 C4 120.9(12) . . ? C6 C5 Cl1 118.5(10) . . ? C4 C5 Cl1 120.5(7) . . ? C7 C6 C5 119.4(13) . . ? C7 C6 H6 120.3 . . ? C5 C6 H6 120.3 . . ? C6 C7 C2 120.5(9) . . ? C6 C7 H7 119.8 . . ? C2 C7 H7 119.8 . . ? C9 C8 C9 121.2(12) 3_565 . ? C9 C8 C1 120.9(9) 3_565 . ? C9 C8 C1 117.8(8) . . ? C8 C9 C8 118.8(12) 2_665 . ? C8 C9 H9 120.6 2_665 . ? C8 C9 H9 120.6 . . ? C10 N2 C11 127.5(8) . . ? C10 N2 H2 116.3 . . ? C11 N2 H2 116.3 . . ? O2 C10 N2 123.8(10) . . ? O2 C10 C17 120.3(12) . . ? N2 C10 C17 115.9(9) . . ? C16 C11 C12 119.3(12) . . ? C16 C11 N2 117.7(8) . . ? C12 C11 N2 123.0(12) . . ? C13 C12 C11 120.1(12) . . ? C13 C12 H12 120.0 . . ? C11 C12 H12 119.9 . . ? C12 C13 C14 119.7(8) . . ? C12 C13 H13 120.2 . . ? C14 C13 H13 120.2 . . ? C15 C14 C13 120.8(11) . . ? C15 C14 Cl2 119.6(10) . . ? C13 C14 Cl2 119.5(7) . . ? C16 C15 C14 119.3(12) . . ? C16 C15 H15 120.3 . . ? C14 C15 H15 120.3 . . ? C15 C16 C11 120.6(9) . . ? C15 C16 H16 119.7 . . ? C11 C16 H16 119.7 . . ? C18 C17 C18 119.9(10) 2_665 . ? C18 C17 C10 122.1(12) 2_665 . ? C18 C17 C10 118.0(8) . . ? C17 C18 C17 120.1(10) 3_565 . ? C17 C18 H18 120.0 3_565 . ? C17 C18 H18 120.0 . . ? C1A O1A C4A 110(4) . . ? O1A C1A C2A 103(4) . . ? O1A C1A H1A1 111.2 . . ? C2A C1A H1A1 111.2 . . ? O1A C1A H1A2 111.2 . . ? C2A C1A H1A2 111.2 . . ? H1A1 C1A H1A2 109.2 . . ? C3A C2A C1A 111(5) . . ? C3A C2A H2A1 109.5 . . ? C1A C2A H2A1 109.6 . . ? C3A C2A H2A2 109.4 . . ? C1A C2A H2A2 109.5 . . ? H2A1 C2A H2A2 108.1 . . ? C2A C3A C4A 102(5) . . ? C2A C3A H3A1 111.4 . . ? C4A C3A H3A1 111.3 . . ? C2A C3A H3A2 111.4 . . ? C4A C3A H3A2 111.4 . . ? H3A1 C3A H3A2 109.3 . . ? O1A C4A C3A 106(4) . . ? O1A C4A H4A1 110.5 . . ? C3A C4A H4A1 110.4 . . ? O1A C4A H4A2 110.5 . . ? C3A C4A H4A2 110.5 . . ? H4A1 C4A H4A2 108.8 . . ? C1B O1B C4B 108(3) . . ? O1B C1B C2B 102(5) . . ? O1B C1B H1B1 111.5 . . ? C2B C1B H1B1 111.3 . . ? O1B C1B H1B2 111.5 . . ? C2B C1B H1B2 111.5 . . ? H1B1 C1B H1B2 109.3 . . ? C3B C2B C1B 112(5) . . ? C3B C2B H2B1 109.2 . . ? C1B C2B H2B1 109.4 . . ? C3B C2B H2B2 109.2 . . ? C1B C2B H2B2 109.5 . . ? H2B1 C2B H2B2 108.0 . . ? C2B C3B C4B 103(5) . . ? C2B C3B H3B1 110.9 . . ? C4B C3B H3B1 111.1 . . ? C2B C3B H3B2 111.0 . . ? C4B C3B H3B2 111.1 . . ? H3B1 C3B H3B2 109.2 . . ? C3B C4B O1B 106(5) . . ? C3B C4B H4B1 110.4 . . ? O1B C4B H4B1 110.5 . . ? C3B C4B H4B2 110.4 . . ? O1B C4B H4B2 110.6 . . ? H4B1 C4B H4B2 108.7 . . ? 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 N1 H1 O2 0.86 2.09 2.890(13) 155 2_665 N2 H2 O1 0.86 2.15 2.962(11) 157 1_554 _refine_diff_density_max 0.73 _refine_diff_density_min -0.44 _refine_diff_density_rms 0.27 data_1F _database_code_depnum_ccdc_archive 'CCDC 778390' #TrackingRef 'kb.cif.txt' _audit_creation_method SHELXL-97 _chemical_name_systematic ; ? ; _chemical_name_common ? _chemical_melting_point ? _chemical_formula_moiety ? _chemical_formula_sum 'C27 H18 F3 N3 O3' _chemical_formula_weight 489.44 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' O O 0.0106 0.0060 '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' _symmetry_cell_setting Orthorhombic _symmetry_space_group_name_H-M Pbca loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x+1/2, -y, z+1/2' '-x, y+1/2, -z+1/2' 'x+1/2, -y+1/2, -z' '-x, -y, -z' 'x-1/2, y, -z-1/2' 'x, -y-1/2, z-1/2' '-x-1/2, y-1/2, z' _cell_length_a 7.1319(3) _cell_length_b 25.1912(12) _cell_length_c 25.6790(12) _cell_angle_alpha 90.00 _cell_angle_beta 90.00 _cell_angle_gamma 90.00 _cell_volume 4613.5(4) _cell_formula_units_Z 8 _cell_measurement_temperature 293(2) _cell_measurement_reflns_used 4305 _cell_measurement_theta_min 1.59 _cell_measurement_theta_max 25.50 _exptl_crystal_description 'rectangular rods' _exptl_crystal_colour colorless _exptl_crystal_size_max 0.20 _exptl_crystal_size_mid 0.12 _exptl_crystal_size_min 0.08 _exptl_crystal_density_meas ? _exptl_crystal_density_diffrn 1.409 _exptl_crystal_density_method 'not measured' _exptl_crystal_F_000 2016 _exptl_absorpt_coefficient_mu 0.110 _exptl_absorpt_correction_type empirical _exptl_absorpt_correction_T_min 0.984 _exptl_absorpt_correction_T_max 0.991 _exptl_absorpt_process_details Sadabs _exptl_special_details ; ? ; _diffrn_ambient_temperature 293(2) _diffrn_radiation_wavelength 0.71073 _diffrn_radiation_type MoK\a _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_monochromator graphite _diffrn_measurement_device_type 'Bruker APEX-2 CCD' _diffrn_measurement_method hemisphere _diffrn_detector_area_resol_mean ? _diffrn_standards_number ? _diffrn_standards_interval_count ? _diffrn_standards_interval_time ? _diffrn_standards_decay_% ? _diffrn_reflns_number 53722 _diffrn_reflns_av_R_equivalents 0.1658 _diffrn_reflns_av_sigmaI/netI 0.0663 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_k_min -29 _diffrn_reflns_limit_k_max 30 _diffrn_reflns_limit_l_min -31 _diffrn_reflns_limit_l_max 30 _diffrn_reflns_theta_min 1.59 _diffrn_reflns_theta_max 25.50 _reflns_number_total 4305 _reflns_number_gt 2340 _reflns_threshold_expression >2sigma(I) _computing_data_collection ? _computing_cell_refinement ? _computing_data_reduction ? _computing_structure_solution 'SHELXS-97 (Sheldrick, 1990)' _computing_structure_refinement 'SHELXL-97 (Sheldrick, 1997)' _computing_molecular_graphics ? _computing_publication_material ? _refine_special_details ; Refinement of F^2^ against ALL reflections. The weighted R-factor wR and goodness of fit S are based on F^2^, conventional R-factors R are based on F, with F set to zero for negative F^2^. The threshold expression of F^2^ > 2sigma(F^2^) is used only for calculating R-factors(gt) etc. and is not relevant to the choice of reflections for refinement. R-factors based on F^2^ are statistically about twice as large as those based on F, and R- factors based on ALL data will be even larger. ; _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_weighting_scheme calc _refine_ls_weighting_details 'calc w=1/[\s^2^(Fo^2^)+(0.1000P)^2^+0.0000P] where P=(Fo^2^+2Fc^2^)/3' _atom_sites_solution_primary direct _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_ls_hydrogen_treatment constr _refine_ls_extinction_method none _refine_ls_extinction_coef ? _refine_ls_number_reflns 4305 _refine_ls_number_parameters 325 _refine_ls_number_restraints 0 _refine_ls_R_factor_all 0.1268 _refine_ls_R_factor_gt 0.0534 _refine_ls_wR_factor_ref 0.1600 _refine_ls_wR_factor_gt 0.1306 _refine_ls_goodness_of_fit_ref 0.862 _refine_ls_restrained_S_all 0.862 _refine_ls_shift/su_max 0.000 _refine_ls_shift/su_mean 0.000 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 _atom_site_disorder_assembly _atom_site_disorder_group O7 O 0.1756(3) 0.38626(8) 0.47324(8) 0.0429(6) Uani 1 1 d . . . O8 O 0.2079(3) 0.21228(8) 0.63847(7) 0.0422(6) Uani 1 1 d . . . O9 O 0.2135(3) 0.15193(8) 0.41084(8) 0.0514(6) Uani 1 1 d . . . C1 C 0.3143(4) 0.30752(11) 0.50644(10) 0.0290(7) Uani 1 1 d . . . C2 C 0.3183(4) 0.27988(11) 0.55299(11) 0.0319(7) Uani 1 1 d . . . H2 H 0.3144 0.2983 0.5843 0.038 Uiso 1 1 calc R . . C3 C 0.3280(4) 0.22470(11) 0.55324(10) 0.0300(7) Uani 1 1 d . . . C4 C 0.3291(4) 0.19771(11) 0.50665(10) 0.0315(7) Uani 1 1 d . . . H4 H 0.3317 0.1608 0.5068 0.038 Uiso 1 1 calc R . . C5 C 0.3262(4) 0.22467(11) 0.45942(10) 0.0303(7) Uani 1 1 d . . . C6 C 0.3198(4) 0.27975(11) 0.45965(10) 0.0320(7) Uani 1 1 d . . . H6 H 0.3191 0.2982 0.4283 0.038 Uiso 1 1 calc R . . C7 C 0.2825(4) 0.36645(11) 0.50550(11) 0.0323(7) Uani 1 1 d . . . C8 C 0.3176(4) 0.19676(11) 0.60487(10) 0.0313(7) Uani 1 1 d . . . C9 C 0.3113(4) 0.19245(11) 0.41067(11) 0.0331(7) Uani 1 1 d . . . F11 F 0.4271(3) 0.60797(7) 0.58150(8) 0.0682(6) Uani 1 1 d . . . N11 N 0.3738(4) 0.39375(9) 0.54246(9) 0.0361(6) Uani 1 1 d . . . H11 H 0.4434 0.3751 0.5628 0.043 Uiso 1 1 calc R . . C11 C 0.3715(4) 0.44886(11) 0.55268(11) 0.0335(7) Uani 1 1 d . . . C12 C 0.2702(5) 0.48536(12) 0.52388(12) 0.0407(8) Uani 1 1 d . . . H12 H 0.1897 0.4739 0.4977 0.049 Uiso 1 1 calc R . . C13 C 0.2892(5) 0.53892(12) 0.53426(13) 0.0479(9) Uani 1 1 d . . . H13 H 0.2232 0.5638 0.5147 0.057 Uiso 1 1 calc R . . C14 C 0.4042(5) 0.55487(12) 0.57296(13) 0.0460(9) Uani 1 1 d . . . C15 C 0.4982(5) 0.52024(13) 0.60387(13) 0.0481(9) Uani 1 1 d . . . H15 H 0.5720 0.5323 0.6313 0.058 Uiso 1 1 calc R . . C16 C 0.4815(5) 0.46642(12) 0.59358(12) 0.0450(8) Uani 1 1 d . . . H16 H 0.5446 0.4420 0.6143 0.054 Uiso 1 1 calc R . . F21 F 0.4344(4) 0.00296(8) 0.76470(8) 0.0855(8) Uani 1 1 d . . . N21 N 0.4354(3) 0.15533(9) 0.61063(8) 0.0353(6) Uani 1 1 d . . . H21 H 0.5186 0.1512 0.5867 0.042 Uiso 1 1 calc R . . C21 C 0.4371(4) 0.11781(11) 0.65193(11) 0.0340(7) Uani 1 1 d . . . C22 C 0.5036(5) 0.06743(12) 0.64138(12) 0.0428(8) Uani 1 1 d . . . H22 H 0.5497 0.0595 0.6084 0.051 Uiso 1 1 calc R . . C23 C 0.5021(5) 0.02894(13) 0.67916(13) 0.0538(9) Uani 1 1 d . . . H23 H 0.5455 -0.0051 0.6719 0.065 Uiso 1 1 calc R . . C24 C 0.4363(5) 0.04132(14) 0.72725(13) 0.0536(10) Uani 1 1 d . . . C25 C 0.3723(5) 0.09038(14) 0.73917(13) 0.0566(10) Uani 1 1 d . . . H25 H 0.3285 0.0978 0.7725 0.068 Uiso 1 1 calc R . . C26 C 0.3727(5) 0.12933(13) 0.70126(11) 0.0483(9) Uani 1 1 d . . . H26 H 0.3295 0.1633 0.7090 0.058 Uiso 1 1 calc R . . F31 F 0.3502(3) 0.14023(9) 0.16585(7) 0.0738(7) Uani 1 1 d . . . N31 N 0.4031(3) 0.21004(9) 0.36886(8) 0.0350(6) Uani 1 1 d . . . H31 H 0.4774 0.2365 0.3736 0.042 Uiso 1 1 calc R . . C31 C 0.3910(4) 0.18971(12) 0.31722(10) 0.0325(7) Uani 1 1 d . . . C32 C 0.4321(5) 0.22436(13) 0.27670(11) 0.0415(8) Uani 1 1 d . . . H32 H 0.4681 0.2591 0.2839 0.050 Uiso 1 1 calc R . . C33 C 0.4194(5) 0.20736(14) 0.22589(11) 0.0485(9) Uani 1 1 d . . . H33 H 0.4465 0.2303 0.1985 0.058 Uiso 1 1 calc R . . C34 C 0.3664(5) 0.15637(15) 0.21648(12) 0.0497(9) Uani 1 1 d . . . C35 C 0.3302(5) 0.12112(14) 0.25498(13) 0.0503(9) Uani 1 1 d . . . H35 H 0.2964 0.0863 0.2472 0.060 Uiso 1 1 calc R . . C36 C 0.3445(5) 0.13794(12) 0.30619(11) 0.0421(8) Uani 1 1 d . . . H36 H 0.3226 0.1141 0.3332 0.051 Uiso 1 1 calc R . . 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 O7 0.0503(14) 0.0325(11) 0.0459(12) 0.0053(10) -0.0201(11) 0.0016(10) O8 0.0539(14) 0.0391(12) 0.0337(11) 0.0013(9) 0.0116(10) 0.0122(11) O9 0.0648(17) 0.0473(14) 0.0422(12) -0.0128(10) 0.0181(11) -0.0269(13) C1 0.0285(16) 0.0278(16) 0.0308(15) 0.0034(12) -0.0039(12) 0.0011(13) C2 0.0311(17) 0.0313(17) 0.0332(16) -0.0037(13) -0.0036(13) 0.0031(13) C3 0.0288(17) 0.0304(16) 0.0308(16) 0.0020(12) -0.0002(13) 0.0017(13) C4 0.0311(17) 0.0297(16) 0.0338(16) 0.0021(13) 0.0011(13) 0.0018(13) C5 0.0261(17) 0.0351(16) 0.0298(15) -0.0022(12) -0.0015(12) 0.0005(13) C6 0.0319(17) 0.0369(17) 0.0273(15) 0.0027(12) -0.0003(12) -0.0007(14) C7 0.0341(17) 0.0287(16) 0.0342(16) 0.0062(13) 0.0010(14) -0.0015(14) C8 0.0376(18) 0.0251(15) 0.0311(15) -0.0004(12) -0.0008(13) 0.0022(14) C9 0.0327(17) 0.0320(16) 0.0344(16) -0.0007(13) 0.0006(13) -0.0032(15) F11 0.0733(15) 0.0298(11) 0.1016(17) -0.0173(10) 0.0138(12) -0.0025(10) N11 0.0485(17) 0.0252(13) 0.0347(14) 0.0009(10) -0.0166(12) 0.0036(12) C11 0.0403(18) 0.0270(16) 0.0331(16) -0.0015(13) -0.0044(14) -0.0001(14) C12 0.046(2) 0.0313(17) 0.0445(18) -0.0018(14) -0.0063(15) 0.0033(15) C13 0.054(2) 0.0291(18) 0.060(2) 0.0041(16) 0.0011(18) 0.0089(16) C14 0.052(2) 0.0247(17) 0.061(2) -0.0080(16) 0.0177(18) -0.0006(16) C15 0.056(2) 0.042(2) 0.047(2) -0.0116(16) 0.0003(17) -0.0060(18) C16 0.058(2) 0.0325(18) 0.0442(19) 0.0006(15) -0.0070(16) 0.0013(16) F21 0.115(2) 0.0697(15) 0.0714(15) 0.0417(12) 0.0120(14) 0.0141(14) N21 0.0394(16) 0.0356(14) 0.0308(13) 0.0054(11) 0.0099(11) 0.0094(12) C21 0.0312(18) 0.0388(17) 0.0319(16) 0.0059(14) -0.0012(13) 0.0027(14) C22 0.055(2) 0.0376(18) 0.0361(17) 0.0015(14) 0.0013(15) 0.0123(16) C23 0.070(3) 0.0375(19) 0.054(2) 0.0081(16) -0.0075(19) 0.0124(18) C24 0.062(3) 0.051(2) 0.047(2) 0.0222(17) -0.0032(18) 0.005(2) C25 0.068(3) 0.061(2) 0.040(2) 0.0159(17) 0.0132(18) 0.012(2) C26 0.061(2) 0.046(2) 0.0381(18) 0.0069(15) 0.0102(16) 0.0104(18) F31 0.0869(17) 0.1009(17) 0.0337(11) -0.0212(11) -0.0049(10) 0.0102(14) N31 0.0411(15) 0.0394(14) 0.0245(12) -0.0013(11) 0.0004(11) -0.0156(12) C31 0.0277(16) 0.0411(18) 0.0287(16) -0.0018(13) 0.0003(12) -0.0037(14) C32 0.044(2) 0.0472(19) 0.0333(18) 0.0058(15) -0.0027(14) -0.0033(16) C33 0.052(2) 0.063(2) 0.0306(18) 0.0079(16) -0.0001(15) 0.0044(19) C34 0.048(2) 0.070(3) 0.0310(18) -0.0121(18) -0.0004(15) 0.0082(19) C35 0.053(2) 0.050(2) 0.048(2) -0.0179(17) 0.0056(17) -0.0007(18) C36 0.051(2) 0.0419(18) 0.0339(17) -0.0032(14) 0.0103(15) -0.0074(16) _geom_special_details ; All esds (except the esd in the dihedral angle between two l.s. planes) are estimated using the full covariance matrix. The cell esds are taken into account individually in the estimation of esds in distances, angles and torsion angles; correlations between esds in cell parameters are only used when they are defined by crystal symmetry. An approximate (isotropic) treatment of cell esds is used for estimating esds involving l.s. planes. ; 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 O7 C7 1.232(3) . ? O8 C8 1.228(3) . ? O9 C9 1.236(3) . ? C1 C2 1.384(4) . ? C1 C6 1.391(4) . ? C1 C7 1.502(4) . ? C2 C3 1.392(4) . ? C3 C4 1.376(4) . ? C3 C8 1.503(4) . ? C4 C5 1.390(4) . ? C5 C6 1.388(4) . ? C5 C9 1.496(4) . ? C7 N11 1.341(3) . ? C8 N21 1.348(3) . ? C9 N31 1.333(3) . ? F11 C14 1.365(3) . ? N11 C11 1.413(4) . ? C11 C16 1.383(4) . ? C11 C12 1.384(4) . ? C12 C13 1.382(4) . ? C13 C14 1.350(5) . ? C14 C15 1.357(5) . ? C15 C16 1.387(4) . ? F21 C24 1.363(3) . ? N21 C21 1.421(3) . ? C21 C26 1.378(4) . ? C21 C22 1.382(4) . ? C22 C23 1.371(4) . ? C23 C24 1.357(5) . ? C24 C25 1.352(5) . ? C25 C26 1.382(4) . ? F31 C34 1.367(3) . ? N31 C31 1.424(3) . ? C31 C36 1.375(4) . ? C31 C32 1.389(4) . ? C32 C33 1.376(4) . ? C33 C34 1.361(5) . ? C34 C35 1.354(5) . ? C35 C36 1.385(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 C6 119.5(3) . . ? C2 C1 C7 121.0(2) . . ? C6 C1 C7 119.2(2) . . ? C3 C2 C1 120.5(3) . . ? C4 C3 C2 119.3(3) . . ? C4 C3 C8 122.4(2) . . ? C2 C3 C8 118.0(2) . . ? C3 C4 C5 121.1(3) . . ? C6 C5 C4 119.0(3) . . ? C6 C5 C9 122.9(3) . . ? C4 C5 C9 117.8(2) . . ? C5 C6 C1 120.5(3) . . ? O7 C7 N11 124.7(3) . . ? O7 C7 C1 120.3(3) . . ? N11 C7 C1 115.0(2) . . ? O8 C8 N21 124.5(3) . . ? O8 C8 C3 120.1(2) . . ? N21 C8 C3 115.4(2) . . ? O9 C9 N31 123.7(3) . . ? O9 C9 C5 119.0(3) . . ? N31 C9 C5 117.3(3) . . ? C7 N11 C11 129.1(2) . . ? C16 C11 C12 119.3(3) . . ? C16 C11 N11 116.7(3) . . ? C12 C11 N11 124.0(3) . . ? C13 C12 C11 119.6(3) . . ? C14 C13 C12 119.5(3) . . ? C13 C14 F11 118.8(3) . . ? C13 C14 C15 122.7(3) . . ? F11 C14 C15 118.5(3) . . ? C14 C15 C16 118.3(3) . . ? C11 C16 C15 120.4(3) . . ? C8 N21 C21 127.0(2) . . ? C26 C21 C22 119.2(3) . . ? C26 C21 N21 122.9(3) . . ? C22 C21 N21 117.9(3) . . ? C23 C22 C21 120.5(3) . . ? C24 C23 C22 118.9(3) . . ? C23 C24 C25 122.2(3) . . ? C23 C24 F21 118.8(3) . . ? C25 C24 F21 119.0(3) . . ? C24 C25 C26 119.2(3) . . ? C21 C26 C25 119.9(3) . . ? C9 N31 C31 126.9(2) . . ? C36 C31 C32 119.5(3) . . ? C36 C31 N31 123.2(3) . . ? C32 C31 N31 117.3(3) . . ? C31 C32 C33 120.1(3) . . ? C34 C33 C32 118.7(3) . . ? F31 C34 C33 118.2(3) . . ? F31 C34 C35 118.9(3) . . ? C33 C34 C35 122.9(3) . . ? C34 C35 C36 118.6(3) . . ? C31 C36 C35 120.2(3) . . ? _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 25.50 _diffrn_measured_fraction_theta_full 1.000 _refine_diff_density_max 0.195 _refine_diff_density_min -0.206 _refine_diff_density_rms 0.048