# Electronic Supplementary Material (ESI) for CrystEngComm # This journal is © The Royal Society of Chemistry 2012 data_global _journal_name_full CrystEngComm _journal_coden_cambridge 1350 #TrackingRef '- CrystallographicData.cif' #============================================================================== _publ_contact_author_name 'Paul D. Beer' _publ_contact_author_address ; Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford OX1 3TA, UK. ; _publ_contact_author_email paul.beer@chem.ox.ac.uk _publ_section_title ; Iodo-imidazolium Salts: Halogen Bonding in Crystals and Anion-Templated Pseudorotaxanes ; loop_ _publ_author_name _publ_author_address 'Antonio Caballero' ; Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford OX1 3TA, UK. ; 'Sam Bennett' ; Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford OX1 3TA, UK. ; 'Christopher J. Serpell' ; Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford, OX1 3TA. UK. ; 'Paul D. Beer' ; Chemistry Research Laboratory, University of Oxford, Mansfield Road, Oxford OX1 3TA, UK. ; _publ_section_abstract ; The 2-iodoimidazolium group is exploited in the anion-templated assembly of pseudorotaxanes with isophthalamide containing macrocycles. Crystallographic and solution-phase studies illustrate that the iodo-imidazolium motif is a potent halogen bond donor, forming the most stable interpenetrated assemblies in solution with the chloride anion template. ; #============================================================================== data_3-I _database_code_depnum_ccdc_archive 'CCDC 892520' #TrackingRef '- CrystallographicData.cif' #============================================================================== _audit_creation_date 10-12-16 _audit_creation_method CRYSTALS_ver_14.07 _oxford_structure_analysis_title 052CJS10 _chemical_name_systematic . _chemical_melting_point . # start Validation Reply Form _vrf_PLAT434_3-I ; PROBLEM: Short Inter HL..A Contact I1 .. I2 .. 3.29 Ang. RESPONSE: This short contact is a result of halogen bonding. See P. Metrangolo, F. Meyer, T. Pilati, G. Resnati and G. Terraneo, Angew. Chem. Int. Ed., 2008, 47, 6114-6127 for a review on the subject. ; # end Validation Reply Form _cell_length_a 14.0437(3) _cell_length_b 16.4599(3) _cell_length_c 9.3843(2) _cell_angle_alpha 90 _cell_angle_beta 99.7969(8) _cell_angle_gamma 90 _cell_volume 2137.62(8) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 21/c 1 ' _symmetry_space_group_name_Hall '-P 2ybc' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z -x,y+1/2,-z+1/2 x,-y+1/2,z+1/2 loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4' I -0.4742 1.8119 20.1472 4.3470 18.9949 0.3814 7.5138 27.7660 2.2735 66.8776 4.0712 'International Tables Vol C 4.2.6.8 and 6.1.1.4' Cl 0.1484 0.1585 11.4604 0.0104 7.1964 1.1662 6.2556 18.5194 1.6455 47.7784 -9.5574 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 4 # Given Formula = C12 I2 # Dc = 1.24 Fooo = 1016.00 Mu = 29.19 M = 397.94 # Found Formula = C17 H32.00 I2 N2 # Dc = 1.61 FOOO = 1016.00 Mu = 29.41 M = 518.26 _chemical_formula_sum 'C17 H32 I2 N2' _chemical_formula_moiety 'C17 H32 I N2, I' _chemical_compound_source . _chemical_formula_weight 518.26 _cell_measurement_reflns_used 4613 _cell_measurement_theta_min 5 _cell_measurement_theta_max 27 _cell_measurement_temperature 150 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_min 0.090 _exptl_crystal_size_mid 0.300 _exptl_crystal_size_max 0.480 _exptl_crystal_density_diffrn 1.610 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 1016 _exptl_absorpt_coefficient_mu 2.941 # Sheldrick geometric approximatio 0.41 0.77 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _exptl_absorpt_correction_T_min 0.61 _exptl_absorpt_correction_T_max 0.77 # For a Kappa CCD, set Tmin to 1.0 and # Tmax to the ratio of max:min frame scales in scale_all.log _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_device Area _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method \w # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'COLLECT (Nonius, 2001).' _computing_cell_refinement 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_structure_solution 'Superflip (Palatinus & Chapuis, 2007)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time . _diffrn_standards_interval_count . _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 150 _diffrn_reflns_number 21791 _reflns_number_total 4845 _diffrn_reflns_av_R_equivalents 0.028 # Number of reflections without Friedels Law is 8902 # Number of reflections with Friedels Law is 4845 # Theoretical number of reflections is about 4899 _diffrn_reflns_theta_min 5.169 _diffrn_reflns_theta_max 27.477 _diffrn_measured_fraction_theta_max 0.989 _diffrn_reflns_theta_full 26.927 _diffrn_measured_fraction_theta_full 0.989 _diffrn_reflns_limit_h_min -18 _diffrn_reflns_limit_h_max 18 _diffrn_reflns_limit_k_min -21 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 12 _reflns_limit_h_min 0 _reflns_limit_h_max 18 _reflns_limit_k_min -21 _reflns_limit_k_max 0 _reflns_limit_l_min -12 _reflns_limit_l_max 12 _oxford_diffrn_Wilson_B_factor 2.06 _oxford_diffrn_Wilson_scale 12.24 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -1.72 _refine_diff_density_max 0.97 # The current dictionary definitions do not cover the # situation where the reflections used for refinement were # selected by a user-defined sigma threshold # The values actually used during refinement _oxford_reflns_threshold_expression_ref I>-3.0\s(I) _refine_ls_number_reflns 4845 _refine_ls_number_restraints 62 _refine_ls_number_parameters 227 _oxford_refine_ls_R_factor_ref 0.0460 _refine_ls_wR_factor_ref 0.0821 _refine_ls_goodness_of_fit_ref 1.0483 _refine_ls_shift/su_max 0.0008770 _refine_ls_shift/su_mean 0.0000174 # The values computed from all data _oxford_reflns_number_all 4845 _refine_ls_R_factor_all 0.0460 _refine_ls_wR_factor_all 0.0821 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 3992 _refine_ls_R_factor_gt 0.0346 _refine_ls_wR_factor_gt 0.0694 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration . _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_hydrogen_treatment none # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 11.3 14.5 4.68 ; # Insert your own references if required - in alphabetical order _publ_section_references ; Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Nonius (2001). COLLECT. Nonius BV, Delft, The Netherlands. Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, edited by C. W. Carter Jr & R. M. Sweet, pp. 307--326. New York: Academic Press. Palatinus, L. & Chapuis, G. (2007). J. Appl. Cryst. 40, 786-790. Prince, E. Mathematical Techniques in Crystallography and Materials Science Springer-Verlag, New York, 1982. Watkin D.J. (1994). Acta Cryst, A50, 411-437. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical Crystallography Laboratory, Oxford, UK. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atomsattached to an atom. # ..._refinement_flags_... # . no refinement constraints S special position constraint on site # G rigid group refinement of site R riding atom # D distance or angle restraint on site T thermal displacement constraints # U Uiso or Uij restraint (rigid bond) P partial occupancy constraint 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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _oxford_atom_site_special_shape _atom_site_attached_hydrogens I1 I 0.53369(3) 0.33249(2) 1.00546(3) 0.0285 1.0000 Uani . . . . . . . I2 I 0.43288(2) 0.41897(2) 0.70107(3) 0.0231 1.0000 Uani . . . . . . . C3 C 0.3739(3) 0.4756(3) 0.5031(5) 0.0210 1.0000 Uani . . . . . . . N4 N 0.3620(3) 0.4408(2) 0.3719(4) 0.0215 1.0000 Uani . . . . . . . C5 C 0.3241(4) 0.4981(3) 0.2677(5) 0.0246 1.0000 Uani . . . . . . . C6 C 0.3143(3) 0.5686(3) 0.3384(5) 0.0237 1.0000 Uani . . . . . . . N7 N 0.3453(3) 0.5533(2) 0.4859(4) 0.0196 1.0000 Uani . . . . . . . C8 C 0.3070(4) 0.4803(4) 0.1090(5) 0.0333 1.0000 Uani . . . . . . . C9 C 0.2833(4) 0.6502(3) 0.2811(6) 0.0332 1.0000 Uani . . . . . . . C10 C 0.3832(4) 0.3559(3) 0.3413(6) 0.0299 1.0000 Uani . U . . . . . C11 C 0.2922(4) 0.3038(4) 0.3090(6) 0.0350 0.36(2) Uani . U P . 1 . . C13 C 0.1676(14) 0.2224(15) 0.423(2) 0.0409 0.36(2) Uani . U P . 1 . . C24 C 0.0720(8) 0.2559(10) 0.4926(18) 0.0661 0.64(2) Uani . U P . 2 . . C25 C -0.0242(15) 0.2102(15) 0.443(3) 0.0849 0.64(2) Uani . U P . 2 . . C16 C 0.3452(4) 0.6131(3) 0.6015(6) 0.0274 1.0000 Uani . . . . . . . C17 C 0.2439(4) 0.6257(3) 0.6367(6) 0.0335 1.0000 Uani . . . . . . . C18 C 0.1982(4) 0.5505(4) 0.6852(6) 0.0333 1.0000 Uani . . . . . . . C19 C 0.0956(4) 0.5655(4) 0.7124(8) 0.0461 1.0000 Uani . . . . . . . C20 C 0.0453(5) 0.4910(5) 0.7584(10) 0.0574 1.0000 Uani . . . . . . . C21 C -0.0589(5) 0.5093(6) 0.7787(12) 0.0784 1.0000 Uani . . . . . . . C22 C 0.2306(9) 0.3042(9) 0.4264(14) 0.0400 0.64(2) Uani . U P . 2 . . C23 C 0.1366(9) 0.2564(8) 0.3790(16) 0.0477 0.64(2) Uani . U P . 2 . . C14 C 0.0776(15) 0.2718(13) 0.406(3) 0.0487 0.36(2) Uani . U P . 1 . . C15 C -0.017(2) 0.2198(19) 0.378(5) 0.0644 0.36(2) Uani . U P . 1 . . C12 C 0.2586(18) 0.2740(16) 0.444(3) 0.0385 0.36(2) Uani . U P . 1 . . C26 C 0.2922(4) 0.3038(4) 0.3090(6) 0.0350 0.64(2) Uani . . P . 2 . . H81 H 0.2983 0.5311 0.0575 0.0513 1.0000 Uiso R . . . . . . H83 H 0.3632 0.4530 0.0856 0.0512 1.0000 Uiso R . . . . . . H82 H 0.2494 0.4473 0.0864 0.0510 1.0000 Uiso R . . . . . . H92 H 0.3230 0.6921 0.3358 0.0513 1.0000 Uiso R . . . . . . H91 H 0.2911 0.6536 0.1798 0.0514 1.0000 Uiso R . . . . . . H93 H 0.2154 0.6586 0.2872 0.0516 1.0000 Uiso R . . . . . . H112 H 0.3051 0.2564 0.2536 0.0420 0.36(2) Uiso R . P . 1 . . H111 H 0.2404 0.3357 0.2535 0.0421 0.36(2) Uiso R . P . 1 . . H132 H 0.1689 0.1853 0.5041 0.0519 0.36(2) Uiso R . P . 1 . . H131 H 0.1665 0.1913 0.3351 0.0520 0.36(2) Uiso R . P . 1 . . H241 H 0.1058 0.2296 0.5796 0.0851 0.64(2) Uiso R . P . 2 . . H242 H 0.0583 0.3125 0.5136 0.0851 0.64(2) Uiso R . P . 2 . . H252 H -0.0639 0.2131 0.5170 0.1270 0.64(2) Uiso R . P . 2 . . H253 H -0.0110 0.1543 0.4242 0.1270 0.64(2) Uiso R . P . 2 . . H251 H -0.0575 0.2347 0.3556 0.1271 0.64(2) Uiso R . P . 2 . . H161 H 0.3867 0.5918 0.6869 0.0328 1.0000 Uiso R . . . . . . H162 H 0.3699 0.6646 0.5706 0.0328 1.0000 Uiso R . . . . . . H171 H 0.2474 0.6658 0.7120 0.0412 1.0000 Uiso R . . . . . . H172 H 0.2028 0.6462 0.5490 0.0410 1.0000 Uiso R . . . . . . H181 H 0.2380 0.5316 0.7741 0.0412 1.0000 Uiso R . . . . . . H182 H 0.1960 0.5092 0.6116 0.0411 1.0000 Uiso R . . . . . . H192 H 0.0982 0.6068 0.7869 0.0573 1.0000 Uiso R . . . . . . H191 H 0.0571 0.5853 0.6225 0.0571 1.0000 Uiso R . . . . . . H202 H 0.0823 0.4712 0.8493 0.0724 1.0000 Uiso R . . . . . . H201 H 0.0447 0.4492 0.6851 0.0721 1.0000 Uiso R . . . . . . H211 H -0.0901 0.4597 0.7991 0.1220 1.0000 Uiso R . . . . . . H213 H -0.0576 0.5467 0.8573 0.1221 1.0000 Uiso R . . . . . . H212 H -0.0934 0.5333 0.6914 0.1221 1.0000 Uiso R . . . . . . H222 H 0.2666 0.2805 0.5141 0.0512 0.64(2) Uiso R . P . 2 . . H221 H 0.2137 0.3601 0.4451 0.0510 0.64(2) Uiso R . P . 2 . . H231 H 0.1527 0.2002 0.3620 0.0622 0.64(2) Uiso R . P . 2 . . H232 H 0.1014 0.2802 0.2900 0.0621 0.64(2) Uiso R . P . 2 . . H141 H 0.0800 0.3041 0.4929 0.0641 0.36(2) Uiso R . P . 1 . . H142 H 0.0766 0.3079 0.3235 0.0640 0.36(2) Uiso R . P . 1 . . H151 H -0.0716 0.2546 0.3507 0.0850 0.36(2) Uiso R . P . 1 . . H152 H -0.0224 0.1916 0.4658 0.0850 0.36(2) Uiso R . P . 1 . . H153 H -0.0138 0.1810 0.3025 0.0850 0.36(2) Uiso R . P . 1 . . H121 H 0.3114 0.2428 0.4985 0.0470 0.36(2) Uiso R . P . 1 . . H122 H 0.2455 0.3213 0.4996 0.0470 0.36(2) Uiso R . P . 1 . . H261 H 0.3115 0.2480 0.2944 0.0419 0.64(2) Uiso R . P . 2 . . H262 H 0.2523 0.3237 0.2200 0.0420 0.64(2) Uiso R . P . 2 . . H101 H 0.4242 0.3340 0.4231 0.0363 1.0000 Uiso R . . . . . . H102 H 0.4153 0.3544 0.2600 0.0363 1.0000 Uiso 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 I1 0.03895(19) 0.02742(17) 0.01885(15) 0.00069(12) 0.00414(13) 0.00314(14) I2 0.02252(15) 0.02706(16) 0.01957(15) 0.00212(12) 0.00286(11) -0.00105(12) C3 0.019(2) 0.026(2) 0.018(2) 0.0062(18) 0.0036(17) -0.0017(18) N4 0.0207(19) 0.023(2) 0.0212(19) 0.0058(16) 0.0037(15) -0.0023(16) C5 0.024(2) 0.031(3) 0.018(2) 0.0028(19) 0.0040(18) 0.001(2) C6 0.017(2) 0.029(3) 0.024(2) 0.005(2) 0.0022(18) -0.0013(19) N7 0.0170(18) 0.024(2) 0.0178(18) -0.0012(15) 0.0032(14) 0.0002(15) C8 0.040(3) 0.039(3) 0.020(2) 0.000(2) 0.002(2) -0.001(2) C9 0.033(3) 0.030(3) 0.036(3) 0.002(2) 0.002(2) 0.004(2) C10 0.037(3) 0.028(3) 0.027(3) -0.001(2) 0.011(2) 0.008(2) C11 0.044(3) 0.029(3) 0.030(3) -0.005(2) 0.003(2) -0.005(2) C13 0.037(7) 0.049(11) 0.035(9) 0.003(8) 0.001(6) -0.004(5) C24 0.030(5) 0.097(10) 0.068(8) 0.033(8) 0.000(4) -0.007(5) C25 0.050(7) 0.062(11) 0.14(2) 0.027(12) 0.014(8) -0.019(7) C16 0.032(3) 0.025(2) 0.026(2) -0.003(2) 0.006(2) -0.004(2) C17 0.036(3) 0.030(3) 0.036(3) -0.007(2) 0.012(2) 0.004(2) C18 0.031(3) 0.036(3) 0.036(3) 0.000(2) 0.013(2) -0.001(2) C19 0.033(3) 0.048(4) 0.063(4) 0.008(3) 0.022(3) 0.006(3) C20 0.036(3) 0.058(5) 0.084(6) 0.006(4) 0.027(4) -0.005(3) C21 0.036(4) 0.084(6) 0.122(8) 0.035(6) 0.034(5) 0.005(4) C22 0.039(5) 0.040(7) 0.041(6) -0.001(5) 0.007(5) -0.006(4) C23 0.040(6) 0.039(6) 0.061(7) 0.004(5) 0.001(4) -0.007(5) C14 0.041(8) 0.040(10) 0.061(14) 0.000(9) -0.003(10) -0.003(6) C15 0.037(7) 0.027(11) 0.12(3) 0.011(15) -0.004(14) 0.003(7) C12 0.042(8) 0.042(11) 0.035(7) -0.021(7) 0.018(8) -0.007(7) C26 0.044(3) 0.029(3) 0.030(3) -0.005(2) 0.003(2) -0.005(2) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.21366(10) loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag I1 . I2 . 3.2885(4) yes I2 . C3 . 2.117(4) yes C3 . N4 . 1.342(6) yes C3 . N7 . 1.342(6) yes N4 . C5 . 1.397(6) yes N4 . C10 . 1.467(6) yes C5 . C6 . 1.356(7) yes C5 . C8 . 1.497(7) yes C6 . N7 . 1.401(6) yes C6 . C9 . 1.484(7) yes N7 . C16 . 1.465(6) yes C8 . H81 . 0.963 no C8 . H83 . 0.966 no C8 . H82 . 0.968 no C9 . H92 . 0.977 no C9 . H91 . 0.977 no C9 . H93 . 0.974 no C10 . C11 . 1.526(8) yes C10 . H101 . 0.950 no C10 . H102 . 0.950 no C11 . C12 . 1.51(2) yes C11 . H112 . 0.971 no C11 . H111 . 0.973 no C13 . C14 . 1.49(3) yes C13 . C12 . 1.52(3) yes C13 . H132 . 0.970 no C13 . H131 . 0.971 no C24 . C25 . 1.55(2) yes C24 . C23 . 1.513(19) yes C24 . H241 . 0.974 no C24 . H242 . 0.977 no C25 . H252 . 0.963 no C25 . H253 . 0.961 no C25 . H251 . 0.961 no C16 . C17 . 1.527(7) yes C16 . H161 . 0.973 no C16 . H162 . 0.979 no C17 . C18 . 1.500(8) yes C17 . H171 . 0.962 no C17 . H172 . 0.981 no C18 . C19 . 1.526(8) yes C18 . H181 . 0.973 no C18 . H182 . 0.966 no C19 . C20 . 1.514(9) yes C19 . H192 . 0.971 no C19 . H191 . 0.978 no C20 . C21 . 1.537(9) yes C20 . H202 . 0.977 no C20 . H201 . 0.973 no C21 . H211 . 0.961 no C21 . H213 . 0.958 no C21 . H212 . 0.963 no C22 . C23 . 1.535(15) yes C22 . C26 . 1.513(14) yes C22 . H222 . 0.971 no C22 . H221 . 0.973 no C23 . H231 . 0.972 no C23 . H232 . 0.977 no C14 . C15 . 1.56(3) yes C14 . H141 . 0.970 no C14 . H142 . 0.973 no C15 . H151 . 0.960 no C15 . H152 . 0.960 no C15 . H153 . 0.961 no C12 . H121 . 0.972 no C12 . H122 . 0.972 no C26 . H261 . 0.974 no C26 . H262 . 0.980 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag I1 . I2 . C3 . 177.57(12) yes I2 . C3 . N4 . 125.9(3) yes I2 . C3 . N7 . 126.1(3) yes N4 . C3 . N7 . 108.0(4) yes C3 . N4 . C5 . 109.1(4) yes C3 . N4 . C10 . 126.0(4) yes C5 . N4 . C10 . 124.8(4) yes N4 . C5 . C6 . 107.1(4) yes N4 . C5 . C8 . 122.9(5) yes C6 . C5 . C8 . 129.9(5) yes C5 . C6 . N7 . 106.8(4) yes C5 . C6 . C9 . 130.2(5) yes N7 . C6 . C9 . 122.9(5) yes C6 . N7 . C3 . 109.1(4) yes C6 . N7 . C16 . 124.8(4) yes C3 . N7 . C16 . 126.1(4) yes C5 . C8 . H81 . 108.4 no C5 . C8 . H83 . 108.5 no H81 . C8 . H83 . 109.2 no C5 . C8 . H82 . 108.3 no H81 . C8 . H82 . 110.4 no H83 . C8 . H82 . 111.9 no C6 . C9 . H92 . 110.1 no C6 . C9 . H91 . 109.3 no H92 . C9 . H91 . 108.7 no C6 . C9 . H93 . 109.7 no H92 . C9 . H93 . 110.3 no H91 . C9 . H93 . 108.7 no N4 . C10 . C11 . 112.5(4) yes N4 . C10 . H101 . 108.6 no C11 . C10 . H101 . 108.6 no N4 . C10 . H102 . 108.8 no C11 . C10 . H102 . 108.8 no H101 . C10 . H102 . 109.5 no C10 . C11 . C12 . 112.8(9) yes C10 . C11 . H112 . 109.4 no C12 . C11 . H112 . 107.6 no C10 . C11 . H111 . 109.1 no C12 . C11 . H111 . 108.3 no H112 . C11 . H111 . 109.6 no C14 . C13 . C12 . 112.8(18) yes C14 . C13 . H132 . 109.4 no C12 . C13 . H132 . 110.3 no C14 . C13 . H131 . 107.7 no C12 . C13 . H131 . 107.1 no H132 . C13 . H131 . 109.3 no C25 . C24 . C23 . 112.8(15) yes C25 . C24 . H241 . 108.2 no C23 . C24 . H241 . 109.2 no C25 . C24 . H242 . 109.4 no C23 . C24 . H242 . 107.4 no H241 . C24 . H242 . 109.8 no C24 . C25 . H252 . 110.0 no C24 . C25 . H253 . 109.6 no H252 . C25 . H253 . 109.5 no C24 . C25 . H251 . 109.0 no H252 . C25 . H251 . 109.8 no H253 . C25 . H251 . 109.1 no N7 . C16 . C17 . 111.7(4) yes N7 . C16 . H161 . 107.0 no C17 . C16 . H161 . 108.7 no N7 . C16 . H162 . 108.5 no C17 . C16 . H162 . 109.7 no H161 . C16 . H162 . 111.2 no C16 . C17 . C18 . 114.6(5) yes C16 . C17 . H171 . 108.6 no C18 . C17 . H171 . 108.3 no C16 . C17 . H172 . 107.5 no C18 . C17 . H172 . 108.5 no H171 . C17 . H172 . 109.2 no C17 . C18 . C19 . 112.5(5) yes C17 . C18 . H181 . 108.1 no C19 . C18 . H181 . 109.2 no C17 . C18 . H182 . 109.1 no C19 . C18 . H182 . 108.5 no H181 . C18 . H182 . 109.4 no C18 . C19 . C20 . 114.6(6) yes C18 . C19 . H192 . 108.2 no C20 . C19 . H192 . 108.9 no C18 . C19 . H191 . 108.0 no C20 . C19 . H191 . 107.5 no H192 . C19 . H191 . 109.6 no C19 . C20 . C21 . 112.1(6) yes C19 . C20 . H202 . 108.4 no C21 . C20 . H202 . 109.5 no C19 . C20 . H201 . 108.7 no C21 . C20 . H201 . 109.4 no H202 . C20 . H201 . 108.7 no C20 . C21 . H211 . 109.5 no C20 . C21 . H213 . 109.2 no H211 . C21 . H213 . 109.9 no C20 . C21 . H212 . 109.1 no H211 . C21 . H212 . 109.7 no H213 . C21 . H212 . 109.4 no C23 . C22 . C26 . 110.9(10) yes C23 . C22 . H222 . 109.8 no C26 . C22 . H222 . 109.6 no C23 . C22 . H221 . 108.2 no C26 . C22 . H221 . 108.8 no H222 . C22 . H221 . 109.5 no C22 . C23 . C24 . 112.8(11) yes C22 . C23 . H231 . 108.8 no C24 . C23 . H231 . 107.1 no C22 . C23 . H232 . 109.1 no C24 . C23 . H232 . 109.2 no H231 . C23 . H232 . 109.8 no C13 . C14 . C15 . 113.4(19) yes C13 . C14 . H141 . 107.5 no C15 . C14 . H141 . 110.4 no C13 . C14 . H142 . 108.5 no C15 . C14 . H142 . 107.7 no H141 . C14 . H142 . 109.2 no C14 . C15 . H151 . 109.7 no C14 . C15 . H152 . 108.3 no H151 . C15 . H152 . 109.7 no C14 . C15 . H153 . 110.3 no H151 . C15 . H153 . 109.4 no H152 . C15 . H153 . 109.5 no C13 . C12 . C11 . 116.9(16) yes C13 . C12 . H121 . 108.7 no C11 . C12 . H121 . 107.1 no C13 . C12 . H122 . 106.5 no C11 . C12 . H122 . 107.8 no H121 . C12 . H122 . 109.7 no C10 . C26 . C22 . 114.6(6) yes C10 . C26 . H261 . 108.4 no C22 . C26 . H261 . 108.3 no C10 . C26 . H262 . 108.6 no C22 . C26 . H262 . 107.7 no H261 . C26 . H262 . 109.1 no _chemical_name_common . #===END #============================================================================== data_3-Cl _database_code_depnum_ccdc_archive 'CCDC 892521' #TrackingRef '- CrystallographicData.cif' #============================================================================== _audit_creation_date 11-02-15 _audit_creation_method CRYSTALS_ver_14.07 _oxford_structure_analysis_title 053CJS10 _chemical_name_systematic . _chemical_melting_point . # start Validation Reply Form _vrf_PLAT220_3-Cl ; PROBLEM: Large Non-Solvent C Ueq(max)/Ueq(min) ... 4.2 Ratio RESPONSE: This ratio is not unexpected, and represents the difference in rigidity between the aromatic central imidazolium units of the cations, and the flexible alkyl chains at the periphery. ; # end Validation Reply Form _cell_length_a 8.8992(5) _cell_length_b 9.1246(5) _cell_length_c 14.5130(8) _cell_angle_alpha 108.091(5) _cell_angle_beta 93.709(4) _cell_angle_gamma 106.155(4) _cell_volume 1061.15(10) _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1 ' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0181 0.0091 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0492 0.0322 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' S 0.3331 0.5567 6.9053 1.4679 5.2034 22.2151 1.4379 0.2536 1.5863 56.1720 0.8669 'International Tables Vol C 4.2.6.8 and 6.1.1.4' I -0.3257 6.8362 20.1472 4.3470 18.9949 0.3814 7.5138 27.7660 2.2735 66.8776 4.0712 'International Tables Vol C 4.2.6.8 and 6.1.1.4' Cl 0.3639 0.7018 11.4604 0.0104 7.1964 1.1662 6.2556 18.5194 1.6455 47.7784 -9.5574 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0311 0.0180 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 2 # Given Formula = C11 H10 Cl0.50 I0.50 N1 O2 S1 # Dc = 1.89 Fooo = 456.00 Mu = 151.60 M = 602.90 # Found Formula = C8.50 H17.00 Cl0.50 I0.50 N1 O0.50 # Dc = 1.39 FOOO = 456.00 Mu = 130.31 M = 444.83 _chemical_formula_sum 'C17 H34 Cl I N2 O' _chemical_formula_moiety 'C17 H32 I N2, Cl, H2 O' _chemical_compound_source ? _chemical_formula_weight 444.81 _cell_measurement_reflns_used 8634 _cell_measurement_theta_min 3 _cell_measurement_theta_max 76 _cell_measurement_temperature 150 _exptl_crystal_description block _exptl_crystal_colour yellow _exptl_crystal_size_min 0.060 _exptl_crystal_size_mid 0.075 _exptl_crystal_size_max 0.075 _exptl_crystal_density_diffrn 1.392 _exptl_crystal_density_meas . _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 456 _exptl_absorpt_coefficient_mu 13.031 # Sheldrick geometric approximatio 0.38 0.46 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.41 (release 13-09-2010 CrysAlis171 .NET) (compiled Sep 13 2010,14:28:38) Empirical absorption correction using spherical harmonics, implemented in SCALE3 ABSPACK scaling algorithm. ; _exptl_absorpt_correction_T_min 0.15 _exptl_absorpt_correction_T_max 0.46 _diffrn_measurement_device_type 'SuperNova, Dual, Cu at zero, Atlas' _diffrn_measurement_device Serial _diffrn_radiation_monochromator mirror _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54180 _diffrn_measurement_method \w # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.41 (release 13-09-2010 CrysAlis171 .NET) (compiled Sep 13 2010,14:28:38) ; _computing_cell_refinement ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.41 (release 13-09-2010 CrysAlis171 .NET) (compiled Sep 13 2010,14:28:38) ; _computing_data_reduction ; CrysAlisPro, Oxford Diffraction Ltd., Version 1.171.34.41 (release 13-09-2010 CrysAlis171 .NET) (compiled Sep 13 2010,14:28:38) ; _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time 0 _diffrn_standards_interval_count 0 _diffrn_standards_number 0 _diffrn_standards_decay_% 0 _diffrn_ambient_temperature 150 _diffrn_reflns_number 10946 _reflns_number_total 4371 _diffrn_reflns_av_R_equivalents 0.032 # Number of reflections without Friedels Law is 10946 # Number of reflections with Friedels Law is 4371 # Theoretical number of reflections is about 4442 _diffrn_reflns_theta_min 3.248 _diffrn_reflns_theta_max 76.185 _diffrn_measured_fraction_theta_max 0.983 _diffrn_reflns_theta_full 73.900 _diffrn_measured_fraction_theta_full 0.997 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 10 _diffrn_reflns_limit_l_min -18 _diffrn_reflns_limit_l_max 18 _reflns_limit_h_min -11 _reflns_limit_h_max 11 _reflns_limit_k_min -11 _reflns_limit_k_max 10 _reflns_limit_l_min 0 _reflns_limit_l_max 18 _oxford_diffrn_Wilson_B_factor 2.40 _oxford_diffrn_Wilson_scale 0.04 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -1.64 _refine_diff_density_max 2.42 # The current dictionary definitions do not cover the # situation where the reflections used for refinement were # selected by a user-defined sigma threshold # The values actually used during refinement _oxford_reflns_threshold_expression_ref I>-3.0\s(I) _refine_ls_number_reflns 4354 _refine_ls_number_restraints 163 _refine_ls_number_parameters 291 _oxford_refine_ls_R_factor_ref 0.0436 _refine_ls_wR_factor_ref 0.1087 _refine_ls_goodness_of_fit_ref 1.0779 _refine_ls_shift/su_max 0.0003348 _refine_ls_shift/su_mean 0.0000121 # The values computed from all data _oxford_reflns_number_all 4355 _refine_ls_R_factor_all 0.0436 _refine_ls_wR_factor_all 0.1087 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 4158 _refine_ls_R_factor_gt 0.0422 _refine_ls_wR_factor_gt 0.1067 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration . _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_hydrogen_treatment none # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 0.192E+04 0.306E+04 0.171E+04 621. ; # Insert your own references if required - in alphabetical order _publ_section_references ; User-defined data collection reference User defined data reduction User defined cell refinement Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M.C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435. Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, edited by C. W. Carter Jr & R. M. Sweet, pp. 307--326. New York: Academic Press. Prince, E. Mathematical Techniques in Crystallography and Materials Science Springer-Verlag, New York, 1982. Watkin D.J. (1994). Acta Cryst, A50, 411-437. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical Crystallography Laboratory, Oxford, UK. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atomsattached to an atom. # ..._refinement_flags_... # . no refinement constraints S special position constraint on site # G rigid group refinement of site R riding atom # D distance or angle restraint on site T thermal displacement constraints # U Uiso or Uij restraint (rigid bond) P partial occupancy constraint 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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _oxford_atom_site_special_shape _atom_site_attached_hydrogens Cl1 Cl 0.07990(15) 0.32614(16) 0.08444(12) 0.0456 1.0000 Uani . . . . . . . I2 I 0.29063(3) 0.14415(3) 0.12043(2) 0.0311 1.0000 Uani . . . . . . . C3 C 0.4389(5) 0.0102(5) 0.1397(3) 0.0263 1.0000 Uani . . . . . . . N4 N 0.3919(4) -0.1417(5) 0.1415(3) 0.0275 1.0000 Uani . U . . . . . C5 C 0.5231(6) -0.1940(6) 0.1472(4) 0.0339 1.0000 Uani . . . . . . . C6 C 0.6519(6) -0.0697(6) 0.1503(4) 0.0316 1.0000 Uani . . . . . . . N7 N 0.5970(4) 0.0569(5) 0.1453(3) 0.0266 1.0000 Uani . U . . . . . C8 C 0.5092(7) -0.3619(7) 0.1473(6) 0.0505 1.0000 Uani . . . . . . . C9 C 0.8231(6) -0.0576(7) 0.1573(5) 0.0421 1.0000 Uani . . . . . . . C10 C 0.2280(6) -0.2331(6) 0.1463(4) 0.0330 0.328(17) Uani . U P . 3 . . C11 C 0.184(3) -0.160(3) 0.2515(15) 0.0445 0.328(17) Uani . U P . 3 . . C12 C 0.284(3) -0.178(5) 0.3279(17) 0.0850 0.328(17) Uani . U P . 3 . . C13 C 0.239(5) -0.131(5) 0.426(3) 0.0895 0.328(17) Uani D U P . 3 . . C14 C 0.296(4) 0.046(5) 0.490(2) 0.0932 0.328(17) Uani D U P . 3 . . C15 C 0.280(5) 0.084(7) 0.595(3) 0.0986 0.328(17) Uani . U P . 3 . . C16 C 0.6985(6) 0.2181(6) 0.1481(4) 0.0333 0.579(14) Uani . U P . 2 . . C17 C 0.7869(12) 0.3198(11) 0.2519(7) 0.0354 0.579(14) Uani . U P . 2 . . C18 C 0.6796(19) 0.358(2) 0.3273(10) 0.0491 0.579(14) Uani . U P . 2 . . C19 C 0.777(2) 0.452(3) 0.4309(11) 0.0499 0.579(14) Uani D U P . 2 . . C20 C 0.6758(18) 0.481(2) 0.5103(9) 0.0760 0.579(14) Uani D U P . 2 . . C21 C 0.773(4) 0.568(2) 0.6133(18) 0.0633 0.579(14) Uani . U P . 2 . . C30 C 0.2280(6) -0.2331(6) 0.1463(4) 0.0330 0.672(17) Uani . U P . 4 . . C31 C 0.2085(12) -0.2351(15) 0.2489(7) 0.0421 0.672(17) Uani . U P . 4 . . C32 C 0.2343(11) -0.0695(12) 0.3243(6) 0.0449 0.672(17) Uani . U P . 4 . . C33 C 0.2199(17) -0.0714(16) 0.4288(10) 0.0587 0.672(17) Uani . U P . 4 . . C34 C 0.242(2) 0.089(2) 0.5052(9) 0.0816 0.672(17) Uani . U P . 4 . . C35 C 0.222(2) 0.077(3) 0.6062(11) 0.1109 0.672(17) Uani . U P . 4 . . C36 C 0.6985(6) 0.2181(6) 0.1481(4) 0.0333 0.421(14) Uani . U P . 1 . . C37 C 0.7005(18) 0.3588(15) 0.2400(10) 0.0368 0.421(14) Uani . U P . 1 . . C38 C 0.730(2) 0.335(3) 0.3351(14) 0.0404 0.421(14) Uani . U P . 1 . . C39 C 0.746(4) 0.482(4) 0.4239(15) 0.0507 0.421(14) Uani D U P . 1 . . C40 C 0.773(2) 0.453(2) 0.5197(10) 0.0576 0.421(14) Uani D U P . 1 . . C41 C 0.794(7) 0.622(4) 0.607(3) 0.0825 0.421(14) Uani . U P . 1 . . O50 O 0.1615(5) 0.4637(5) -0.0889(4) 0.0516 1.0000 Uani . . . . . . . H81 H 0.6085 -0.3838 0.1375 0.0770 1.0000 Uiso R . . . . . . H83 H 0.4832 -0.3705 0.2097 0.0771 1.0000 Uiso R . . . . . . H82 H 0.4272 -0.4404 0.0946 0.0772 1.0000 Uiso R . . . . . . H91 H 0.8694 -0.0120 0.1092 0.0644 1.0000 Uiso R . . . . . . H93 H 0.8774 0.0150 0.2228 0.0644 1.0000 Uiso R . . . . . . H92 H 0.8359 -0.1656 0.1455 0.0645 1.0000 Uiso R . . . . . . H101 H 0.2204 -0.3458 0.1338 0.0389 0.328(17) Uiso R . P . 3 . . H102 H 0.1548 -0.2257 0.0968 0.0390 0.328(17) Uiso R . P . 3 . . H112 H 0.0744 -0.2168 0.2517 0.0560 0.328(17) Uiso R . P . 3 . . H111 H 0.1996 -0.0455 0.2665 0.0561 0.328(17) Uiso R . P . 3 . . H121 H 0.2670 -0.2938 0.3108 0.0990 0.328(17) Uiso R . P . 3 . . H122 H 0.3924 -0.1230 0.3253 0.0990 0.328(17) Uiso R . P . 3 . . H132 H 0.3018 -0.1699 0.4650 0.1030 0.328(17) Uiso R . P . 3 . . H131 H 0.1275 -0.1795 0.4262 0.1030 0.328(17) Uiso R . P . 3 . . H141 H 0.4027 0.1029 0.4846 0.1070 0.328(17) Uiso R . P . 3 . . H142 H 0.2209 0.0882 0.4635 0.1071 0.328(17) Uiso R . P . 3 . . H152 H 0.3432 0.1913 0.6367 0.1400 0.328(17) Uiso R . P . 3 . . H151 H 0.3185 0.0048 0.6111 0.1400 0.328(17) Uiso R . P . 3 . . H153 H 0.1713 0.0659 0.6033 0.1400 0.328(17) Uiso R . P . 3 . . H162 H 0.7751 0.2021 0.1043 0.0400 0.579(14) Uiso R . P . 2 . . H161 H 0.6326 0.2743 0.1268 0.0399 0.579(14) Uiso R . P . 2 . . H171 H 0.8491 0.2599 0.2728 0.0420 0.579(14) Uiso R . P . 2 . . H172 H 0.8570 0.4222 0.2507 0.0420 0.579(14) Uiso R . P . 2 . . H182 H 0.6235 0.4246 0.3090 0.0690 0.579(14) Uiso R . P . 2 . . H181 H 0.6039 0.2567 0.3259 0.0690 0.579(14) Uiso R . P . 2 . . H192 H 0.8421 0.3896 0.4457 0.0631 0.579(14) Uiso R . P . 2 . . H191 H 0.8445 0.5568 0.4317 0.0633 0.579(14) Uiso R . P . 2 . . H201 H 0.6172 0.5506 0.4984 0.0930 0.579(14) Uiso R . P . 2 . . H202 H 0.6019 0.3785 0.5075 0.0930 0.579(14) Uiso R . P . 2 . . H211 H 0.7026 0.5824 0.6602 0.0900 0.579(14) Uiso R . P . 2 . . H213 H 0.8442 0.6710 0.6174 0.0901 0.579(14) Uiso R . P . 2 . . H212 H 0.8323 0.5015 0.6263 0.0900 0.579(14) Uiso R . P . 2 . . H301 H 0.2043 -0.3435 0.1023 0.0389 0.672(17) Uiso R . P . 4 . . H302 H 0.1550 -0.1834 0.1257 0.0392 0.672(17) Uiso R . P . 4 . . H312 H 0.2856 -0.2800 0.2700 0.0542 0.672(17) Uiso R . P . 4 . . H311 H 0.1018 -0.3035 0.2473 0.0539 0.672(17) Uiso R . P . 4 . . H321 H 0.3388 0.0006 0.3256 0.0570 0.672(17) Uiso R . P . 4 . . H322 H 0.1562 -0.0250 0.3043 0.0571 0.672(17) Uiso R . P . 4 . . H332 H 0.3019 -0.1113 0.4491 0.0703 0.672(17) Uiso R . P . 4 . . H331 H 0.1163 -0.1443 0.4268 0.0702 0.672(17) Uiso R . P . 4 . . H342 H 0.3465 0.1621 0.5082 0.1051 0.672(17) Uiso R . P . 4 . . H341 H 0.1599 0.1309 0.4858 0.1051 0.672(17) Uiso R . P . 4 . . H351 H 0.2297 0.1824 0.6514 0.1549 0.672(17) Uiso R . P . 4 . . H352 H 0.3045 0.0407 0.6282 0.1551 0.672(17) Uiso R . P . 4 . . H353 H 0.1200 0.0009 0.6025 0.1550 0.672(17) Uiso R . P . 4 . . H362 H 0.8055 0.2146 0.1436 0.0400 0.421(14) Uiso R . P . 1 . . H361 H 0.6567 0.2388 0.0918 0.0400 0.421(14) Uiso R . P . 1 . . H372 H 0.7842 0.4544 0.2411 0.0459 0.421(14) Uiso R . P . 1 . . H371 H 0.5986 0.3773 0.2341 0.0460 0.421(14) Uiso R . P . 1 . . H381 H 0.8174 0.2907 0.3347 0.0520 0.421(14) Uiso R . P . 1 . . H382 H 0.6342 0.2577 0.3404 0.0520 0.421(14) Uiso R . P . 1 . . H392 H 0.8482 0.5559 0.4238 0.0770 0.421(14) Uiso R . P . 1 . . H391 H 0.6645 0.5328 0.4215 0.0770 0.421(14) Uiso R . P . 1 . . H401 H 0.8610 0.4120 0.5275 0.0720 0.421(14) Uiso R . P . 1 . . H402 H 0.6744 0.3727 0.5189 0.0721 0.421(14) Uiso R . P . 1 . . H412 H 0.7991 0.6059 0.6696 0.1070 0.421(14) Uiso R . P . 1 . . H411 H 0.8904 0.7000 0.6055 0.1070 0.421(14) Uiso R . P . 1 . . H413 H 0.7057 0.6597 0.5973 0.1070 0.421(14) Uiso R . P . 1 . . H501 H 0.1399 0.4268 -0.0427 0.0607 1.0000 Uiso R . . . . . . H502 H 0.0984 0.5189 -0.0880 0.0607 1.0000 Uiso 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 Cl1 0.0307(6) 0.0381(6) 0.0842(10) 0.0371(7) 0.0142(6) 0.0164(5) I2 0.02857(17) 0.02701(17) 0.04177(19) 0.01465(14) 0.00580(13) 0.01156(13) C3 0.028(2) 0.026(2) 0.025(2) 0.0079(18) 0.0046(17) 0.0102(18) N4 0.0236(19) 0.0246(19) 0.033(2) 0.0085(16) 0.0037(15) 0.0077(15) C5 0.031(2) 0.030(2) 0.044(3) 0.014(2) 0.004(2) 0.013(2) C6 0.028(2) 0.032(2) 0.037(3) 0.013(2) 0.0035(19) 0.012(2) N7 0.0223(18) 0.0283(19) 0.0294(19) 0.0109(15) 0.0041(14) 0.0069(15) C8 0.039(3) 0.037(3) 0.084(5) 0.024(3) 0.008(3) 0.022(3) C9 0.026(2) 0.047(3) 0.059(3) 0.022(3) 0.004(2) 0.017(2) C10 0.026(2) 0.027(2) 0.041(2) 0.010(2) 0.0034(19) 0.0047(19) C11 0.043(9) 0.041(10) 0.050(5) 0.019(6) 0.020(6) 0.005(8) C12 0.070(10) 0.142(17) 0.045(5) 0.030(9) 0.013(7) 0.038(11) C13 0.073(10) 0.145(17) 0.048(5) 0.027(10) 0.017(7) 0.035(11) C14 0.075(10) 0.146(17) 0.051(6) 0.024(10) 0.017(7) 0.032(11) C15 0.078(12) 0.150(18) 0.053(6) 0.021(10) 0.023(9) 0.027(12) C16 0.030(2) 0.032(2) 0.036(2) 0.0146(18) 0.0066(19) 0.003(2) C17 0.031(5) 0.028(4) 0.042(3) 0.011(3) 0.002(3) 0.003(3) C18 0.038(8) 0.049(8) 0.041(4) -0.001(5) 0.002(4) 0.005(6) C19 0.036(8) 0.046(10) 0.047(4) -0.005(5) -0.004(4) 0.007(6) C20 0.067(8) 0.091(10) 0.045(5) -0.009(6) 0.006(4) 0.024(8) C21 0.080(12) 0.057(11) 0.046(5) 0.004(8) 0.000(6) 0.028(10) C30 0.026(2) 0.027(2) 0.041(2) 0.010(2) 0.0034(19) 0.0047(19) C31 0.038(5) 0.039(5) 0.047(3) 0.019(3) 0.010(3) 0.003(4) C32 0.046(5) 0.047(5) 0.038(3) 0.016(3) 0.009(4) 0.006(4) C33 0.058(7) 0.072(7) 0.044(4) 0.026(4) 0.016(5) 0.008(6) C34 0.081(9) 0.097(8) 0.044(5) 0.006(5) 0.022(6) 0.010(8) C35 0.083(11) 0.179(18) 0.046(5) 0.021(7) 0.031(7) 0.018(12) C36 0.030(2) 0.032(2) 0.036(2) 0.0146(18) 0.0066(19) 0.003(2) C37 0.040(7) 0.028(4) 0.043(4) 0.015(3) 0.005(5) 0.009(5) C38 0.037(10) 0.047(8) 0.041(4) 0.016(4) 0.005(7) 0.016(8) C39 0.052(13) 0.056(11) 0.045(5) 0.011(5) 0.004(8) 0.026(9) C40 0.060(11) 0.065(10) 0.042(5) 0.010(6) -0.003(7) 0.023(8) C41 0.12(2) 0.073(18) 0.043(7) 0.006(11) 0.004(12) 0.03(2) O50 0.045(2) 0.054(3) 0.075(3) 0.035(2) 0.024(2) 0.026(2) _refine_ls_extinction_method None _oxford_refine_ls_scale 5.29(8) loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag Cl1 . I2 . 2.9482(12) yes I2 . C3 . 2.092(5) yes C3 . N4 . 1.341(6) yes C3 . N7 . 1.341(6) yes N4 . C5 . 1.386(6) yes N4 . C10 . 1.483(6) yes C5 . C6 . 1.356(7) yes C5 . C8 . 1.503(7) yes C6 . N7 . 1.393(6) yes C6 . C9 . 1.491(7) yes N7 . C36 . 1.483(6) yes C8 . H81 . 0.968 no C8 . H83 . 0.970 no C8 . H82 . 0.963 no C9 . H91 . 0.976 no C9 . H93 . 0.974 no C9 . H92 . 0.988 no C10 . C11 . 1.59(2) yes C10 . H101 . 0.969 no C10 . H102 . 0.968 no C11 . C12 . 1.45(4) yes C11 . H112 . 0.969 no C11 . H111 . 0.970 no C12 . C13 . 1.47(4) yes C12 . H121 . 0.970 no C12 . H122 . 0.969 no C13 . C14 . 1.5100(5) yes C13 . H132 . 0.971 no C13 . H131 . 0.970 no C14 . C15 . 1.47(4) yes C14 . H141 . 0.970 no C14 . H142 . 0.971 no C15 . H152 . 0.962 no C15 . H151 . 0.961 no C15 . H153 . 0.961 no C16 . C17 . 1.524(10) yes C16 . H162 . 0.971 no C16 . H161 . 0.972 no C17 . C18 . 1.521(19) yes C17 . H171 . 0.973 no C17 . H172 . 0.974 no C18 . C19 . 1.54(2) yes C18 . H182 . 0.971 no C18 . H181 . 0.973 no C19 . C20 . 1.5100(5) yes C19 . H192 . 0.975 no C19 . H191 . 0.975 no C20 . C21 . 1.52(3) yes C20 . H201 . 0.969 no C20 . H202 . 0.972 no C21 . H211 . 0.959 no C21 . H213 . 0.962 no C21 . H212 . 0.956 no C30 . C31 . 1.516(10) yes C30 . H301 . 0.965 no C30 . H302 . 0.970 no C31 . C32 . 1.510(16) yes C31 . H312 . 0.969 no C31 . H311 . 0.975 no C32 . C33 . 1.536(15) yes C32 . H321 . 0.967 no C32 . H322 . 0.967 no C33 . C34 . 1.486(18) yes C33 . H332 . 0.969 no C33 . H331 . 0.968 no C34 . C35 . 1.520(19) yes C34 . H342 . 0.976 no C34 . H341 . 0.976 no C35 . H351 . 0.960 no C35 . H352 . 0.962 no C35 . H353 . 0.962 no C36 . C37 . 1.532(14) yes C36 . H362 . 0.967 no C36 . H361 . 0.969 no C37 . C38 . 1.48(2) yes C37 . H372 . 0.971 no C37 . H371 . 0.970 no C38 . C39 . 1.50(4) yes C38 . H381 . 0.973 no C38 . H382 . 0.971 no C39 . C40 . 1.5100(5) yes C39 . H392 . 0.973 no C39 . H391 . 0.968 no C40 . C41 . 1.62(4) yes C40 . H401 . 0.972 no C40 . H402 . 0.969 no C41 . H412 . 0.963 no C41 . H411 . 0.960 no C41 . H413 . 0.958 no O50 . H501 . 0.850 no O50 . H502 . 0.850 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag Cl1 . I2 . C3 . 177.65(13) yes I2 . C3 . N4 . 126.1(3) yes I2 . C3 . N7 . 125.9(3) yes N4 . C3 . N7 . 107.9(4) yes C3 . N4 . C5 . 109.1(4) yes C3 . N4 . C10 . 125.3(4) yes C5 . N4 . C10 . 125.3(4) yes N4 . C5 . C6 . 107.1(4) yes N4 . C5 . C8 . 122.2(5) yes C6 . C5 . C8 . 130.7(5) yes C5 . C6 . N7 . 106.9(4) yes C5 . C6 . C9 . 130.4(5) yes N7 . C6 . C9 . 122.7(4) yes C6 . N7 . C3 . 108.9(4) yes C6 . N7 . C36 . 125.2(4) yes C3 . N7 . C36 . 125.9(4) yes C5 . C8 . H81 . 110.0 no C5 . C8 . H83 . 109.5 no H81 . C8 . H83 . 109.4 no C5 . C8 . H82 . 109.4 no H81 . C8 . H82 . 108.7 no H83 . C8 . H82 . 109.7 no C6 . C9 . H91 . 109.7 no C6 . C9 . H93 . 108.5 no H91 . C9 . H93 . 108.7 no C6 . C9 . H92 . 110.5 no H91 . C9 . H92 . 109.7 no H93 . C9 . H92 . 109.7 no N4 . C10 . C11 . 110.6(8) yes N4 . C10 . H101 . 109.0 no C11 . C10 . H101 . 109.2 no N4 . C10 . H102 . 109.0 no C11 . C10 . H102 . 109.3 no H101 . C10 . H102 . 109.7 no C10 . C11 . C12 . 112(2) yes C10 . C11 . H112 . 109.3 no C12 . C11 . H112 . 108.6 no C10 . C11 . H111 . 109.4 no C12 . C11 . H111 . 107.9 no H112 . C11 . H111 . 110.0 no C11 . C12 . C13 . 115(3) yes C11 . C12 . H121 . 106.3 no C13 . C12 . H121 . 103.8 no C11 . C12 . H122 . 107.1 no C13 . C12 . H122 . 114.2 no H121 . C12 . H122 . 109.8 no C12 . C13 . C14 . 119(3) yes C12 . C13 . H132 . 105.0 no C14 . C13 . H132 . 98.1 no C12 . C13 . H131 . 112.9 no C14 . C13 . H131 . 110.7 no H132 . C13 . H131 . 109.5 no C13 . C14 . C15 . 117(3) yes C13 . C14 . H141 . 113.2 no C15 . C14 . H141 . 109.5 no C13 . C14 . H142 . 102.2 no C15 . C14 . H142 . 104.7 no H141 . C14 . H142 . 109.7 no C14 . C15 . H152 . 114.7 no C14 . C15 . H151 . 101.8 no H152 . C15 . H151 . 109.6 no C14 . C15 . H153 . 111.2 no H152 . C15 . H153 . 109.6 no H151 . C15 . H153 . 109.6 no N7 . C16 . C17 . 110.5(5) yes N7 . C16 . H162 . 108.6 no C17 . C16 . H162 . 109.0 no N7 . C16 . H161 . 109.3 no C17 . C16 . H161 . 109.3 no H162 . C16 . H161 . 110.0 no C16 . C17 . C18 . 114.1(9) yes C16 . C17 . H171 . 108.1 no C18 . C17 . H171 . 107.8 no C16 . C17 . H172 . 108.6 no C18 . C17 . H172 . 108.2 no H171 . C17 . H172 . 109.9 no C17 . C18 . C19 . 111.1(12) yes C17 . C18 . H182 . 107.7 no C19 . C18 . H182 . 109.0 no C17 . C18 . H181 . 109.1 no C19 . C18 . H181 . 110.3 no H182 . C18 . H181 . 109.8 no C18 . C19 . C20 . 113.5(14) yes C18 . C19 . H192 . 108.5 no C20 . C19 . H192 . 108.3 no C18 . C19 . H191 . 108.5 no C20 . C19 . H191 . 108.4 no H192 . C19 . H191 . 109.7 no C19 . C20 . C21 . 113.1(16) yes C19 . C20 . H201 . 108.1 no C21 . C20 . H201 . 107.4 no C19 . C20 . H202 . 109.6 no C21 . C20 . H202 . 109.1 no H201 . C20 . H202 . 109.5 no C20 . C21 . H211 . 109.3 no C20 . C21 . H213 . 109.8 no H211 . C21 . H213 . 110.0 no C20 . C21 . H212 . 108.7 no H211 . C21 . H212 . 109.4 no H213 . C21 . H212 . 109.7 no N4 . C30 . C31 . 112.3(5) yes N4 . C30 . H301 . 108.0 no C31 . C30 . H301 . 108.7 no N4 . C30 . H302 . 109.0 no C31 . C30 . H302 . 108.9 no H301 . C30 . H302 . 109.9 no C30 . C31 . C32 . 114.0(9) yes C30 . C31 . H312 . 108.1 no C32 . C31 . H312 . 107.8 no C30 . C31 . H311 . 109.1 no C32 . C31 . H311 . 108.1 no H312 . C31 . H311 . 109.6 no C31 . C32 . C33 . 113.9(9) yes C31 . C32 . H321 . 109.1 no C33 . C32 . H321 . 108.3 no C31 . C32 . H322 . 108.2 no C33 . C32 . H322 . 108.5 no H321 . C32 . H322 . 108.7 no C32 . C33 . C34 . 115.8(10) yes C32 . C33 . H332 . 107.8 no C34 . C33 . H332 . 106.3 no C32 . C33 . H331 . 108.1 no C34 . C33 . H331 . 108.7 no H332 . C33 . H331 . 110.0 no C33 . C34 . C35 . 113.0(15) yes C33 . C34 . H342 . 109.1 no C35 . C34 . H342 . 109.8 no C33 . C34 . H341 . 107.5 no C35 . C34 . H341 . 107.5 no H342 . C34 . H341 . 109.9 no C34 . C35 . H351 . 109.3 no C34 . C35 . H352 . 108.9 no H351 . C35 . H352 . 109.5 no C34 . C35 . H353 . 109.7 no H351 . C35 . H353 . 109.9 no H352 . C35 . H353 . 109.5 no N7 . C36 . C37 . 114.0(6) yes N7 . C36 . H362 . 108.7 no C37 . C36 . H362 . 109.5 no N7 . C36 . H361 . 107.6 no C37 . C36 . H361 . 107.3 no H362 . C36 . H361 . 109.6 no C36 . C37 . C38 . 116.0(13) yes C36 . C37 . H372 . 107.6 no C38 . C37 . H372 . 107.3 no C36 . C37 . H371 . 107.7 no C38 . C37 . H371 . 108.5 no H372 . C37 . H371 . 109.7 no C37 . C38 . C39 . 114.5(18) yes C37 . C38 . H381 . 108.9 no C39 . C38 . H381 . 114.8 no C37 . C38 . H382 . 106.9 no C39 . C38 . H382 . 101.8 no H381 . C38 . H382 . 109.3 no C38 . C39 . C40 . 113(2) yes C38 . C39 . H392 . 102.5 no C40 . C39 . H392 . 102.4 no C38 . C39 . H391 . 115.0 no C40 . C39 . H391 . 112.9 no H392 . C39 . H391 . 109.5 no C39 . C40 . C41 . 107(2) yes C39 . C40 . H401 . 115.1 no C41 . C40 . H401 . 111.5 no C39 . C40 . H402 . 103.6 no C41 . C40 . H402 . 109.6 no H401 . C40 . H402 . 109.7 no C40 . C41 . H412 . 109.8 no C40 . C41 . H411 . 108.1 no H412 . C41 . H411 . 109.7 no C40 . C41 . H413 . 109.7 no H412 . C41 . H413 . 109.7 no H411 . C41 . H413 . 109.7 no H501 . O50 . H502 . 102.5 no loop_ _geom_hbond_atom_site_label_D _geom_hbond_site_symmetry_D _geom_hbond_atom_site_label_H _geom_hbond_site_symmetry_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_angle_DHA _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_publ_flag C8 . H81 . O50 2_655 172 0.97 2.43 3.39(3) yes C9 . H92 . O50 2_655 171 0.99 2.59 3.57(3) yes C13 . H132 . C40 2_656 127 0.97 2.56 3.24(3) yes C20 . H201 . C20 2_666 130 0.97 2.53 3.24(3) yes C37 . H372 . O50 2_665 124 0.97 2.57 3.22(3) yes _chemical_name_common . #===END #============================================================================== data_4-Br _database_code_depnum_ccdc_archive 'CCDC 892522' #TrackingRef '- CrystallographicData.cif' #============================================================================== _audit_creation_date 11-02-04 _audit_creation_method CRYSTALS_ver_14.07 _oxford_structure_analysis_title 003BRM11 _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 8.7542(2) _cell_length_b 9.3695(2) _cell_length_c 13.6378(4) _cell_angle_alpha 71.4823(10) _cell_angle_beta 74.1255(11) _cell_angle_gamma 73.9467(11) _cell_volume 997.94(4) _symmetry_cell_setting Triclinic _symmetry_space_group_name_H-M 'P -1 ' _symmetry_space_group_name_Hall '-P 1' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4' Br -0.2901 2.4595 17.1789 2.1723 5.2358 16.5796 5.6377 0.2609 3.9851 41.4328 2.9557 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 2 # Given Formula = C17 H37 Br1 N2 O2 # Dc = 1.27 Fooo = 388.00 Mu = 20.69 M = 381.40 # Found Formula = C17 H35 Br1 N2 O1 # Dc = 1.21 FOOO = 388.00 Mu = 20.62 M = 363.38 _chemical_formula_sum 'C17 H35 Br1 N2 O1' _chemical_formula_moiety 'C17 H33 N2, Br, H2 O' _chemical_compound_source ? _chemical_formula_weight 363.38 _cell_measurement_reflns_used 3975 _cell_measurement_theta_min 5 _cell_measurement_theta_max 27 _cell_measurement_temperature 150 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_min 0.080 _exptl_crystal_size_mid 0.200 _exptl_crystal_size_max 0.240 _exptl_crystal_density_diffrn 1.209 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 388 _exptl_absorpt_coefficient_mu 2.062 # Sheldrick geometric approximatio 0.66 0.85 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _exptl_absorpt_correction_T_min 0.72 _exptl_absorpt_correction_T_max 0.85 # For a Kappa CCD, set Tmin to 1.0 and # Tmax to the ratio of max:min frame scales in scale_all.log _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_device Area _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method \w # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'COLLECT (Nonius, 2001).' _computing_cell_refinement 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time . _diffrn_standards_interval_count . _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 150 _diffrn_reflns_number 14244 _reflns_number_total 4494 _diffrn_reflns_av_R_equivalents 0.045 # Number of reflections without Friedels Law is 7652 # Number of reflections with Friedels Law is 4494 # Theoretical number of reflections is about 4579 _diffrn_reflns_theta_min 5.177 _diffrn_reflns_theta_max 27.487 _diffrn_measured_fraction_theta_max 0.981 _diffrn_reflns_theta_full 25.562 _diffrn_measured_fraction_theta_full 0.990 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 12 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 17 _reflns_limit_h_min -10 _reflns_limit_h_max 11 _reflns_limit_k_min -11 _reflns_limit_k_max 12 _reflns_limit_l_min 0 _reflns_limit_l_max 17 _oxford_diffrn_Wilson_B_factor 2.51 _oxford_diffrn_Wilson_scale 10.39 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.83 _refine_diff_density_max 0.71 # The current dictionary definitions do not cover the # situation where the reflections used for refinement were # selected by a user-defined sigma threshold # The values actually used during refinement _oxford_reflns_threshold_expression_ref I>-3.0\s(I) _refine_ls_number_reflns 4494 _refine_ls_number_restraints 0 _refine_ls_number_parameters 190 _oxford_refine_ls_R_factor_ref 0.0727 _refine_ls_wR_factor_ref 0.1213 _refine_ls_goodness_of_fit_ref 0.9200 _refine_ls_shift/su_max 0.0004718 _refine_ls_shift/su_mean 0.0000173 # The values computed from all data _oxford_reflns_number_all 4494 _refine_ls_R_factor_all 0.0727 _refine_ls_wR_factor_all 0.1213 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 3269 _refine_ls_R_factor_gt 0.0427 _refine_ls_wR_factor_gt 0.0933 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration . _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_hydrogen_treatment none # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 9.40 12.7 6.37 1.84 ; # Insert your own references if required - in alphabetical order _publ_section_references ; Altomare, A., Cascarano, G., Giacovazzo, C., Guagliardi, A., Burla, M.C., Polidori, G. & Camalli, M. (1994). J. Appl. Cryst. 27, 435. Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Nonius (2001). COLLECT. Nonius BV, Delft, The Netherlands. Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, edited by C. W. Carter Jr & R. M. Sweet, pp. 307--326. New York: Academic Press. Prince, E. Mathematical Techniques in Crystallography and Materials Science Springer-Verlag, New York, 1982. Watkin D.J. (1994). Acta Cryst, A50, 411-437. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical Crystallography Laboratory, Oxford, UK. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atomsattached to an atom. # ..._refinement_flags_... # . no refinement constraints S special position constraint on site # G rigid group refinement of site R riding atom # D distance or angle restraint on site T thermal displacement constraints # U Uiso or Uij restraint (rigid bond) P partial occupancy constraint 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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _oxford_atom_site_special_shape _atom_site_attached_hydrogens Br1 Br 0.32885(5) 0.87974(5) 0.43047(4) 0.0329 1.0000 Uani . . . . . . . O2 O 0.5649(5) 0.7856(4) 0.6095(3) 0.0580 1.0000 Uani . . . . . . . N3 N 0.7668(4) 0.5713(3) 0.3575(2) 0.0260 1.0000 Uani . . . . . . . C4 C 0.9277(4) 0.4930(4) 0.3540(3) 0.0263 1.0000 Uani . . . . . . . C5 C 1.0107(4) 0.5913(4) 0.3617(3) 0.0263 1.0000 Uani . . . . . . . N6 N 0.8987(4) 0.7273(3) 0.3694(2) 0.0257 1.0000 Uani . . . . . . . C7 C 0.7533(4) 0.7117(4) 0.3671(3) 0.0292 1.0000 Uani . . . . . . . C8 C 0.9339(5) 0.8684(4) 0.3771(3) 0.0320 1.0000 Uani . . . . . . . C9 C 1.0003(5) 0.9667(4) 0.2698(3) 0.0337 1.0000 Uani . . . . . . . C10 C 0.8776(5) 1.0497(5) 0.1997(3) 0.0361 1.0000 Uani . . . . . . . C11 C 0.9509(5) 1.1489(5) 0.0942(3) 0.0353 1.0000 Uani . . . . . . . C12 C 0.8318(5) 1.2363(5) 0.0222(4) 0.0419 1.0000 Uani . . . . . . . C13 C 0.9083(6) 1.3349(6) -0.0818(4) 0.0539 1.0000 Uani . . . . . . . C14 C 1.1853(4) 0.5705(5) 0.3613(3) 0.0334 1.0000 Uani . . . . . . . C15 C 0.9857(5) 0.3323(4) 0.3439(3) 0.0347 1.0000 Uani . . . . . . . C16 C 0.6317(5) 0.5119(5) 0.3506(3) 0.0321 1.0000 Uani . . . . . . . C17 C 0.6372(5) 0.5090(4) 0.2395(3) 0.0329 1.0000 Uani . . . . . . . C18 C 0.6079(5) 0.6669(5) 0.1616(3) 0.0340 1.0000 Uani . . . . . . . C19 C 0.6207(5) 0.6571(5) 0.0504(3) 0.0388 1.0000 Uani . . . . . . . C20 C 0.5949(6) 0.8106(6) -0.0290(4) 0.0460 1.0000 Uani . . . . . . . C21 C 0.6154(7) 0.7990(8) -0.1418(4) 0.0652 1.0000 Uani . . . . . . . H71 H 0.6569 0.7850 0.3728 0.0362 1.0000 Uiso R . . . . . . H81 H 0.8340 0.9276 0.4108 0.0384 1.0000 Uiso R . . . . . . H82 H 1.0161 0.8391 0.4209 0.0375 1.0000 Uiso R . . . . . . H91 H 1.0871 0.9024 0.2318 0.0415 1.0000 Uiso R . . . . . . H92 H 1.0412 1.0466 0.2817 0.0425 1.0000 Uiso R . . . . . . H101 H 0.8329 0.9764 0.1878 0.0439 1.0000 Uiso R . . . . . . H102 H 0.7904 1.1150 0.2363 0.0442 1.0000 Uiso R . . . . . . H111 H 1.0408 1.0781 0.0586 0.0414 1.0000 Uiso R . . . . . . H112 H 0.9973 1.2229 0.1062 0.0418 1.0000 Uiso R . . . . . . H121 H 0.7828 1.1640 0.0112 0.0533 1.0000 Uiso R . . . . . . H122 H 0.7471 1.3022 0.0575 0.0524 1.0000 Uiso R . . . . . . H131 H 0.8289 1.3849 -0.1249 0.0800 1.0000 Uiso R . . . . . . H132 H 0.9941 1.2716 -0.1204 0.0794 1.0000 Uiso R . . . . . . H133 H 0.9527 1.4101 -0.0708 0.0797 1.0000 Uiso R . . . . . . H141 H 1.1986 0.6058 0.4152 0.0498 1.0000 Uiso R . . . . . . H142 H 1.2358 0.6298 0.2943 0.0502 1.0000 Uiso R . . . . . . H143 H 1.2368 0.4638 0.3698 0.0500 1.0000 Uiso R . . . . . . H153 H 1.0935 0.2899 0.3563 0.0516 1.0000 Uiso R . . . . . . H152 H 0.9858 0.3294 0.2742 0.0514 1.0000 Uiso R . . . . . . H151 H 0.9143 0.2695 0.3935 0.0517 1.0000 Uiso R . . . . . . H161 H 0.6362 0.4113 0.3974 0.0395 1.0000 Uiso R . . . . . . H162 H 0.5315 0.5786 0.3742 0.0389 1.0000 Uiso R . . . . . . H171 H 0.5545 0.4545 0.2424 0.0414 1.0000 Uiso R . . . . . . H172 H 0.7405 0.4486 0.2133 0.0413 1.0000 Uiso R . . . . . . H181 H 0.5006 0.7292 0.1856 0.0424 1.0000 Uiso R . . . . . . H182 H 0.6884 0.7218 0.1623 0.0416 1.0000 Uiso R . . . . . . H191 H 0.5406 0.6048 0.0540 0.0494 1.0000 Uiso R . . . . . . H192 H 0.7273 0.5999 0.0273 0.0501 1.0000 Uiso R . . . . . . H201 H 0.4843 0.8651 -0.0071 0.0567 1.0000 Uiso R . . . . . . H202 H 0.6739 0.8694 -0.0296 0.0571 1.0000 Uiso R . . . . . . H211 H 0.6002 0.8997 -0.1914 0.0994 1.0000 Uiso R . . . . . . H212 H 0.5367 0.7449 -0.1433 0.1002 1.0000 Uiso R . . . . . . H213 H 0.7224 0.7431 -0.1656 0.0999 1.0000 Uiso R . . . . . . H21 H 0.5920 0.8704 0.5995 0.0706 1.0000 Uiso R . . . . . . H22 H 0.5054 0.8089 0.5645 0.0706 1.0000 Uiso 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 Br1 0.02813(19) 0.03120(19) 0.0420(2) -0.00930(15) -0.00839(14) -0.00937(13) O2 0.087(3) 0.0291(16) 0.071(2) 0.0000(15) -0.045(2) -0.0187(16) N3 0.0235(14) 0.0281(15) 0.0260(15) -0.0048(12) -0.0029(12) -0.0095(12) C4 0.0262(17) 0.0269(17) 0.0251(18) -0.0062(14) -0.0032(14) -0.0074(14) C5 0.0241(17) 0.0289(18) 0.0232(18) -0.0046(14) -0.0039(14) -0.0049(14) N6 0.0252(15) 0.0266(15) 0.0257(15) -0.0074(12) -0.0033(12) -0.0070(12) C7 0.0241(17) 0.0344(19) 0.0296(19) -0.0091(15) -0.0061(14) -0.0054(14) C8 0.0336(19) 0.0297(19) 0.038(2) -0.0140(16) -0.0099(16) -0.0069(15) C9 0.0313(19) 0.0284(19) 0.046(2) -0.0099(17) -0.0125(17) -0.0096(15) C10 0.031(2) 0.033(2) 0.046(2) -0.0120(18) -0.0077(17) -0.0066(16) C11 0.0309(19) 0.035(2) 0.043(2) -0.0118(18) -0.0081(17) -0.0082(16) C12 0.040(2) 0.045(2) 0.042(2) -0.013(2) -0.0102(19) -0.0069(19) C13 0.053(3) 0.061(3) 0.039(3) -0.011(2) -0.008(2) -0.003(2) C14 0.0259(18) 0.037(2) 0.037(2) -0.0063(17) -0.0089(16) -0.0075(15) C15 0.036(2) 0.0250(18) 0.041(2) -0.0080(16) -0.0039(17) -0.0067(15) C16 0.0280(18) 0.038(2) 0.033(2) -0.0075(16) -0.0035(15) -0.0154(16) C17 0.035(2) 0.0313(19) 0.037(2) -0.0095(16) -0.0070(17) -0.0140(16) C18 0.033(2) 0.034(2) 0.039(2) -0.0122(17) -0.0098(17) -0.0072(16) C19 0.038(2) 0.042(2) 0.037(2) -0.0110(18) -0.0053(17) -0.0108(18) C20 0.037(2) 0.054(3) 0.044(3) -0.004(2) -0.0101(19) -0.014(2) C21 0.056(3) 0.096(4) 0.039(3) -0.002(3) -0.011(2) -0.024(3) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.3191(4) loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag O2 . H21 . 0.850 no O2 . H22 . 0.850 no N3 . C4 . 1.392(5) yes N3 . C7 . 1.333(5) yes N3 . C16 . 1.475(4) yes C4 . C5 . 1.364(5) yes C4 . C15 . 1.488(5) yes C5 . N6 . 1.390(5) yes C5 . C14 . 1.485(5) yes N6 . C7 . 1.330(5) yes N6 . C8 . 1.478(5) yes C7 . H71 . 0.932 no C8 . C9 . 1.517(6) yes C8 . H81 . 0.979 no C8 . H82 . 0.986 no C9 . C10 . 1.517(6) yes C9 . H91 . 0.969 no C9 . H92 . 0.986 no C10 . C11 . 1.524(6) yes C10 . H101 . 0.950 no C10 . H102 . 0.966 no C11 . C12 . 1.517(6) yes C11 . H111 . 1.002 no C11 . H112 . 0.968 no C12 . C13 . 1.517(7) yes C12 . H121 . 0.962 no C12 . H122 . 0.951 no C13 . H131 . 0.958 no C13 . H132 . 0.964 no C13 . H133 . 0.960 no C14 . H141 . 0.941 no C14 . H142 . 0.965 no C14 . H143 . 0.960 no C15 . H153 . 0.956 no C15 . H152 . 0.959 no C15 . H151 . 0.956 no C16 . C17 . 1.511(5) yes C16 . H161 . 0.954 no C16 . H162 . 0.967 no C17 . C18 . 1.524(6) yes C17 . H171 . 0.981 no C17 . H172 . 0.967 no C18 . C19 . 1.520(6) yes C18 . H181 . 0.989 no C18 . H182 . 0.985 no C19 . C20 . 1.502(6) yes C19 . H191 . 0.943 no C19 . H192 . 0.963 no C20 . C21 . 1.535(7) yes C20 . H201 . 0.976 no C20 . H202 . 0.992 no C21 . H211 . 0.970 no C21 . H212 . 0.970 no C21 . H213 . 0.963 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag H21 . O2 . H22 . 102.1 no C4 . N3 . C7 . 108.9(3) yes C4 . N3 . C16 . 126.5(3) yes C7 . N3 . C16 . 124.6(3) yes N3 . C4 . C5 . 106.7(3) yes N3 . C4 . C15 . 123.1(3) yes C5 . C4 . C15 . 130.2(3) yes C4 . C5 . N6 . 106.7(3) yes C4 . C5 . C14 . 130.5(3) yes N6 . C5 . C14 . 122.8(3) yes C5 . N6 . C7 . 109.1(3) yes C5 . N6 . C8 . 126.1(3) yes C7 . N6 . C8 . 124.9(3) yes N3 . C7 . N6 . 108.7(3) yes N3 . C7 . H71 . 125.0 no N6 . C7 . H71 . 126.3 no N6 . C8 . C9 . 112.2(3) yes N6 . C8 . H81 . 108.7 no C9 . C8 . H81 . 109.9 no N6 . C8 . H82 . 109.0 no C9 . C8 . H82 . 107.9 no H81 . C8 . H82 . 109.1 no C8 . C9 . C10 . 115.2(3) yes C8 . C9 . H91 . 109.2 no C10 . C9 . H91 . 107.3 no C8 . C9 . H92 . 107.7 no C10 . C9 . H92 . 106.8 no H91 . C9 . H92 . 110.7 no C9 . C10 . C11 . 112.6(3) yes C9 . C10 . H101 . 109.4 no C11 . C10 . H101 . 109.7 no C9 . C10 . H102 . 108.4 no C11 . C10 . H102 . 108.7 no H101 . C10 . H102 . 108.0 no C10 . C11 . C12 . 114.4(3) yes C10 . C11 . H111 . 106.6 no C12 . C11 . H111 . 109.6 no C10 . C11 . H112 . 109.8 no C12 . C11 . H112 . 108.0 no H111 . C11 . H112 . 108.3 no C11 . C12 . C13 . 113.1(4) yes C11 . C12 . H121 . 108.7 no C13 . C12 . H121 . 111.5 no C11 . C12 . H122 . 108.3 no C13 . C12 . H122 . 108.0 no H121 . C12 . H122 . 106.9 no C12 . C13 . H131 . 109.7 no C12 . C13 . H132 . 110.4 no H131 . C13 . H132 . 106.8 no C12 . C13 . H133 . 111.4 no H131 . C13 . H133 . 110.0 no H132 . C13 . H133 . 108.5 no C5 . C14 . H141 . 111.1 no C5 . C14 . H142 . 108.6 no H141 . C14 . H142 . 108.3 no C5 . C14 . H143 . 109.6 no H141 . C14 . H143 . 110.1 no H142 . C14 . H143 . 109.2 no C4 . C15 . H153 . 111.9 no C4 . C15 . H152 . 110.2 no H153 . C15 . H152 . 107.9 no C4 . C15 . H151 . 109.4 no H153 . C15 . H151 . 109.0 no H152 . C15 . H151 . 108.4 no N3 . C16 . C17 . 112.7(3) yes N3 . C16 . H161 . 107.7 no C17 . C16 . H161 . 110.9 no N3 . C16 . H162 . 107.7 no C17 . C16 . H162 . 108.7 no H161 . C16 . H162 . 109.1 no C16 . C17 . C18 . 114.8(3) yes C16 . C17 . H171 . 108.2 no C18 . C17 . H171 . 108.5 no C16 . C17 . H172 . 109.3 no C18 . C17 . H172 . 109.6 no H171 . C17 . H172 . 106.1 no C17 . C18 . C19 . 112.6(3) yes C17 . C18 . H181 . 110.9 no C19 . C18 . H181 . 109.5 no C17 . C18 . H182 . 107.3 no C19 . C18 . H182 . 110.5 no H181 . C18 . H182 . 105.7 no C18 . C19 . C20 . 114.2(4) yes C18 . C19 . H191 . 107.1 no C20 . C19 . H191 . 108.7 no C18 . C19 . H192 . 108.4 no C20 . C19 . H192 . 108.2 no H191 . C19 . H192 . 110.3 no C19 . C20 . C21 . 113.6(4) yes C19 . C20 . H201 . 107.5 no C21 . C20 . H201 . 108.3 no C19 . C20 . H202 . 109.1 no C21 . C20 . H202 . 108.2 no H201 . C20 . H202 . 110.0 no C20 . C21 . H211 . 111.7 no C20 . C21 . H212 . 109.5 no H211 . C21 . H212 . 108.8 no C20 . C21 . H213 . 110.9 no H211 . C21 . H213 . 107.5 no H212 . C21 . H213 . 108.3 no loop_ _geom_hbond_atom_site_label_D _geom_hbond_site_symmetry_D _geom_hbond_atom_site_label_H _geom_hbond_site_symmetry_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_angle_DHA _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_publ_flag C14 . H143 . O2 2_766 164 0.96 2.48 3.416(6) yes #===END #============================================================================== data_5-Br _database_code_depnum_ccdc_archive 'CCDC 892523' #TrackingRef '- CrystallographicData.cif' #============================================================================== # start Validation Reply Form _vrf_PLAT434_5-Br ; PROBLEM: Short Inter HL..A Contact Br1 .. Br2 .. 3.16 Ang. RESPONSE: This short contact is a result of halogen bonding. See P. Metrangolo, F. Meyer, T. Pilati, G. Resnati and G. Terraneo, Angew. Chem. Int. Ed., 2008, 47, 6114-6127 for a review on the subject. ; _vrf_PLAT220_5-Br ; PROBLEM: Large Non-Solvent C Ueq(max)/Ueq(min) ... 5.7 Ratio RESPONSE: This ratio is not unexpected, and represents the difference in rigidity between the aromatic central imidazolium units of the cations, and the flexible alkyl chains at the periphery. ; _vrf_PLAT094_5-Br ; PROBLEM: Ratio of Maximum / Minimum Residual Density .... 2.44 RESPONSE: Such a value could be indicative of missing atoms, or twinning. However, no further sensible assignment of atoms to Q peaks in the difference map was possible (the highest peaks are very close to the bromine atoms), and searching for twins using ROTAX gave neither significant reduction of the R factor, nor diminution of Q peak magnitude. Given these results, we believe the reported structure is representative of the experimental data. ; # end Validation Reply Form _cell_length_a 18.4148(2) _cell_length_b 8.78740(10) _cell_length_c 27.3027(4) _cell_angle_alpha 90 _cell_angle_beta 107.4219(5) _cell_angle_gamma 90 _cell_volume 4215.40(9) _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 2/c ' _symmetry_space_group_name_Hall ? loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z x,-y,z+1/2 -x,y,-z+1/2 loop_ _atom_type_symbol _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_Cromer_Mann_a1 _atom_type_scat_Cromer_Mann_b1 _atom_type_scat_Cromer_Mann_a2 _atom_type_scat_Cromer_Mann_b2 _atom_type_scat_Cromer_Mann_a3 _atom_type_scat_Cromer_Mann_b3 _atom_type_scat_Cromer_Mann_a4 _atom_type_scat_Cromer_Mann_b4 _atom_type_scat_Cromer_Mann_c _atom_type_scat_source C 0.0033 0.0016 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0061 0.0033 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4' Br -0.2901 2.4595 17.1789 2.1723 5.2358 16.5796 5.6377 0.2609 3.9851 41.4328 2.9557 'International Tables Vol C 4.2.6.8 and 6.1.1.4' Cl 0.1484 0.1585 11.4604 0.0104 7.1964 1.1662 6.2556 18.5194 1.6455 47.7784 -9.5574 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0106 0.0060 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 8 # Given Formula = C32 Br4 Cl1.50 N1 O1 # Dc = 1.24 Fooo = 1824.00 Mu = 39.32 M = 787.15 # Found Formula = C34 H68 Br4 N4 O2 # Dc = 1.39 FOOO = 1824.00 Mu = 38.50 M = 884.55 _chemical_formula_sum 'C17 H34 Br2 N2 O' _chemical_formula_moiety 'C17 H32 Br N2, Br, H2 O' _chemical_compound_source ? _chemical_formula_weight 442.26 _cell_measurement_reflns_used 9116 _cell_measurement_theta_min 5 _cell_measurement_theta_max 27 _cell_measurement_temperature 150 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_min 0.210 _exptl_crystal_size_mid 0.220 _exptl_crystal_size_max 0.590 _exptl_crystal_density_diffrn 1.394 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 1824 _exptl_absorpt_coefficient_mu 3.850 # Sheldrick geometric approximatio 0.43 0.45 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _exptl_absorpt_correction_T_min 0.31 _exptl_absorpt_correction_T_max 0.45 # For a Kappa CCD, set Tmin to 1.0 and # Tmax to the ratio of max:min frame scales in scale_all.log _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_measurement_device Area _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method \w # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'COLLECT (Nonius, 2001).' _computing_cell_refinement 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_structure_solution 'Superflip (Palatinus & Chapuis, 2007)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time . _diffrn_standards_interval_count . _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_ambient_temperature 150 _diffrn_reflns_number 46662 _reflns_number_total 9554 _diffrn_reflns_av_R_equivalents 0.036 # Number of reflections without Friedels Law is 14548 # Number of reflections with Friedels Law is 9554 # Theoretical number of reflections is about 8786 _diffrn_reflns_theta_min 5.128 _diffrn_reflns_theta_max 27.509 _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 25.033 _diffrn_measured_fraction_theta_full 0.988 _diffrn_reflns_limit_h_min -23 _diffrn_reflns_limit_h_max 23 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -35 _diffrn_reflns_limit_l_max 35 _reflns_limit_h_min -23 _reflns_limit_h_max 22 _reflns_limit_k_min 0 _reflns_limit_k_max 11 _reflns_limit_l_min 0 _reflns_limit_l_max 35 _oxford_diffrn_Wilson_B_factor 2.10 _oxford_diffrn_Wilson_scale 58.58 _atom_sites_solution_primary Other #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_diff_density_min -0.91 _refine_diff_density_max 2.22 # The current dictionary definitions do not cover the # situation where the reflections used for refinement were # selected by a user-defined sigma threshold # The values actually used during refinement _oxford_reflns_threshold_expression_ref I>-3.0\s(I) _refine_ls_number_reflns 8668 _refine_ls_number_restraints 211 _refine_ls_number_parameters 480 _oxford_refine_ls_R_factor_ref 0.0786 _refine_ls_wR_factor_ref 0.1048 _refine_ls_goodness_of_fit_ref 1.0066 _refine_ls_shift/su_max 0.0011125 _refine_ls_shift/su_mean 0.0000271 # The values computed with all filters except I/sigma _oxford_reflns_number_all 8669 _refine_ls_R_factor_all 0.0786 _refine_ls_wR_factor_all 0.1048 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 6381 _refine_ls_R_factor_gt 0.0507 _refine_ls_wR_factor_gt 0.0948 # choose from: rm (reference molecule of known chirality), # ad (anomolous dispersion - Flack), rmad (rm and ad), # syn (from synthesis), unk (unknown) or . (not applicable). _chemical_absolute_configuration . _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_hydrogen_treatment constr #undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method= Modified Sheldrick w=1/[\s^2^(F^2^) + ( 0.03P)^2^ +18.35P] ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 ; # Insert your own references if required - in alphabetical order _publ_section_references ; Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Nonius (2001). COLLECT. Nonius BV, Delft, The Netherlands. Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, edited by C. W. Carter Jr & R. M. Sweet, pp. 307--326. New York: Academic Press. Palatinus, L. & Chapuis, G. (2007). J. Appl. Cryst. 40, 786-790. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical Crystallography Laboratory, Oxford, UK. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atoms attached to an atom. # ..._refinement_flags_... # . no refinement constraints S special position constraint on site # G rigid group refinement of site R riding atom # D distance or angle restraint on site T thermal displacement constraints # U Uiso or Uij restraint (rigid bond) P partial occupancy constraint 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_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_attached_hydrogens Br1 Br 0.67878(3) 0.40144(5) 0.79354(2) 0.0339 1.0000 Uani . . . . . . Br2 Br 0.57270(3) 0.14469(5) 0.815664(19) 0.0255 1.0000 Uani . . . . . . C3 C 0.5171(3) -0.0296(5) 0.81899(18) 0.0226 1.0000 Uani . U . . . . N4 N 0.4442(2) -0.0355(5) 0.81715(15) 0.0270 1.0000 Uani . U . . . . C5 C 0.4224(3) -0.1880(5) 0.81654(18) 0.0264 1.0000 Uani . U . . . . C6 C 0.4848(3) -0.2729(5) 0.81811(18) 0.0248 1.0000 Uani . . . . . . N7 N 0.5438(2) -0.1716(4) 0.81938(15) 0.0238 1.0000 Uani . . . . . . C8 C 0.3442(3) -0.2362(6) 0.8143(2) 0.0392 1.0000 Uani . . . . . . C9 C 0.4943(3) -0.4406(5) 0.8192(2) 0.0345 1.0000 Uani . . . . . . C10 C 0.3952(4) 0.0984(7) 0.8176(2) 0.0501 0.660(8) Uani D U P . 3 . C11 C 0.3876(6) 0.1283(13) 0.8707(4) 0.0536 0.660(8) Uani D . P . 3 . C12 C 0.4588(6) 0.1768(13) 0.9097(4) 0.0571 0.660(8) Uani D . P . 3 . C13 C 0.4473(8) 0.2162(14) 0.9619(4) 0.0613 0.660(8) Uani D . P . 3 . C14 C 0.5187(7) 0.2699(16) 1.0014(4) 0.0669 0.660(8) Uani D . P . 3 . C15 C 0.5078(8) 0.3036(18) 1.0520(5) 0.0749 0.660(8) Uani D . P . 3 . C16 C 0.6224(3) -0.2147(6) 0.82181(19) 0.0267 1.0000 Uani . . . . . . C17 C 0.6690(3) -0.2624(6) 0.87547(19) 0.0293 1.0000 Uani . . . . . . C18 C 0.6897(3) -0.1334(6) 0.9145(2) 0.0352 1.0000 Uani . . . . . . C19 C 0.7346(4) -0.1935(7) 0.9675(2) 0.0468 1.0000 Uani . . . . . . C20 C 0.7599(5) -0.0693(7) 1.0077(2) 0.0709 1.0000 Uani . . . . . . C21 C 0.7998(5) -0.1366(8) 1.0609(3) 0.0793 1.0000 Uani . . . . . . C60 C 0.3952(4) 0.0984(7) 0.8176(2) 0.0501 0.340(8) Uani D U P . 4 . C61 C 0.4174(13) 0.178(3) 0.8703(8) 0.0526 0.340(8) Uani D . P . 4 . C62 C 0.3983(12) 0.079(2) 0.9118(7) 0.0547 0.340(8) Uani D . P . 4 . C63 C 0.4103(13) 0.165(3) 0.9631(8) 0.0591 0.340(8) Uani D . P . 4 . C64 C 0.4867(15) 0.223(3) 0.9913(8) 0.0632 0.340(8) Uani D . P . 4 . C65 C 0.4815(15) 0.307(3) 1.0386(8) 0.0702 0.340(8) Uani D . P . 4 . Br101 Br 0.82140(3) 0.04849(5) 0.70785(2) 0.0311 1.0000 Uani . . . . . . Br102 Br 0.92630(3) 0.30733(5) 0.685660(19) 0.0250 1.0000 Uani . . . . . . C103 C 0.9820(3) 0.4819(5) 0.68274(17) 0.0204 1.0000 Uani . . . . . . N104 N 1.0555(2) 0.4870(4) 0.68576(15) 0.0234 1.0000 Uani . . . . . . C105 C 1.0768(3) 0.6400(5) 0.68643(19) 0.0263 1.0000 Uani . . . . . . C106 C 1.0143(3) 0.7247(5) 0.68332(18) 0.0232 1.0000 Uani . . . . . . N107 N 0.9556(2) 0.6237(4) 0.68115(14) 0.0213 1.0000 Uani . . . . . . C108 C 1.1564(3) 0.6882(6) 0.6910(2) 0.0365 1.0000 Uani . . . . . . C109 C 1.0043(3) 0.8939(5) 0.6813(2) 0.0314 1.0000 Uani . . . . . . C110 C 1.1043(3) 0.3553(5) 0.68335(19) 0.0281 1.0000 Uani . . . . . . C111 C 1.1069(3) 0.3275(7) 0.6289(2) 0.0481 1.0000 Uani . . . . . . C112 C 1.0345(4) 0.2911(8) 0.5906(2) 0.0510 1.0000 Uani . . . . . . C113 C 1.0416(4) 0.2686(9) 0.5364(2) 0.0624 1.0000 Uani . . . . . . C114 C 0.9670(5) 0.2311(11) 0.4982(3) 0.0825 1.0000 Uani . . . . . . C115 C 0.9738(6) 0.2023(14) 0.4447(3) 0.1160 1.0000 Uani . . . . . . C116 C 0.8750(2) 0.6657(5) 0.6744(2) 0.0277 1.0000 Uani . . . . . . C117 C 0.8326(3) 0.7040(6) 0.6182(2) 0.0382 0.788(10) Uani D . P . 1 . C118 C 0.8290(5) 0.5732(8) 0.5806(2) 0.0448 0.788(10) Uani D . P . 1 . C119 C 0.7949(4) 0.6129(10) 0.5242(3) 0.0478 0.788(10) Uani D . P . 1 . C120 C 0.7111(4) 0.6419(10) 0.5068(3) 0.0579 0.788(10) Uani D . P . 1 . C121 C 0.6804(6) 0.6783(11) 0.4500(3) 0.0678 0.788(10) Uani D . P . 1 . C167 C 0.8326(3) 0.7040(6) 0.6182(2) 0.0382 0.212(10) Uani D . P . 2 . C168 C 0.7917(16) 0.5644(19) 0.5922(10) 0.0443 0.212(10) Uani D . P . 2 . C169 C 0.7382(16) 0.601(4) 0.5402(8) 0.0549 0.212(10) Uani D . P . 2 . C170 C 0.7730(19) 0.636(5) 0.4984(10) 0.0631 0.212(10) Uani D . P . 2 . C171 C 0.719(2) 0.672(5) 0.4464(13) 0.0756 0.212(10) Uani D . P . 2 . O201 O 0.7557(2) 0.0420(4) 0.80905(16) 0.0470 1.0000 Uani . . . . . . O202 O 0.7448(2) 0.4090(4) 0.69274(17) 0.0480 1.0000 Uani . . . . . . H81 H 0.3405 -0.3447 0.8124 0.0579 1.0000 Uiso R . . . . . H82 H 0.3326 -0.2031 0.8444 0.0584 1.0000 Uiso R . . . . . H83 H 0.3076 -0.1935 0.7848 0.0582 1.0000 Uiso R . . . . . H91 H 0.5293 -0.4707 0.8014 0.0509 1.0000 Uiso R . . . . . H92 H 0.5127 -0.4769 0.8536 0.0512 1.0000 Uiso R . . . . . H93 H 0.4462 -0.4865 0.8031 0.0512 1.0000 Uiso R . . . . . H101 H 0.4170 0.1871 0.8063 0.0569 0.660(8) Uiso DR . P . 3 . H102 H 0.3450 0.0793 0.7940 0.0571 0.660(8) Uiso DR . P . 3 . H111 H 0.3705 0.0368 0.8833 0.0598 0.660(8) Uiso DR . P . 3 . H112 H 0.3496 0.2071 0.8676 0.0601 0.660(8) Uiso DR . P . 3 . H121 H 0.4960 0.0955 0.9148 0.0630 0.660(8) Uiso DR . P . 3 . H122 H 0.4785 0.2658 0.8968 0.0631 0.660(8) Uiso DR . P . 3 . H131 H 0.4307 0.1245 0.9749 0.0670 0.660(8) Uiso DR . P . 3 . H132 H 0.4090 0.2948 0.9574 0.0668 0.660(8) Uiso DR . P . 3 . H141 H 0.5574 0.1923 1.0052 0.0709 0.660(8) Uiso DR . P . 3 . H142 H 0.5356 0.3636 0.9892 0.0709 0.660(8) Uiso DR . P . 3 . H151 H 0.5564 0.3316 1.0756 0.0941 0.660(8) Uiso DR . P . 3 . H152 H 0.4888 0.2131 1.0640 0.0940 0.660(8) Uiso DR . P . 3 . H153 H 0.4724 0.3861 1.0494 0.0937 0.660(8) Uiso DR . P . 3 . H161 H 0.6461 -0.1276 0.8115 0.0310 1.0000 Uiso R . . . . . H162 H 0.6214 -0.2978 0.7986 0.0308 1.0000 Uiso R . . . . . H171 H 0.6408 -0.3393 0.8874 0.0340 1.0000 Uiso R . . . . . H172 H 0.7159 -0.3067 0.8730 0.0340 1.0000 Uiso R . . . . . H181 H 0.6442 -0.0841 0.9166 0.0439 1.0000 Uiso R . . . . . H182 H 0.7199 -0.0598 0.9031 0.0438 1.0000 Uiso R . . . . . H191 H 0.7025 -0.2646 0.9787 0.0552 1.0000 Uiso R . . . . . H192 H 0.7796 -0.2462 0.9649 0.0550 1.0000 Uiso R . . . . . H201 H 0.7946 -0.0018 0.9976 0.0831 1.0000 Uiso R . . . . . H202 H 0.7163 -0.0112 1.0094 0.0831 1.0000 Uiso R . . . . . H211 H 0.8146 -0.0569 1.0857 0.1189 1.0000 Uiso R . . . . . H212 H 0.8445 -0.1917 1.0595 0.1189 1.0000 Uiso R . . . . . H213 H 0.7658 -0.2050 1.0704 0.1189 1.0000 Uiso R . . . . . H601 H 0.3427 0.0651 0.8091 0.0570 0.340(8) Uiso DR . P . 4 . H602 H 0.4008 0.1702 0.7920 0.0569 0.340(8) Uiso DR . P . 4 . H611 H 0.4716 0.2000 0.8808 0.0590 0.340(8) Uiso DR . P . 4 . H612 H 0.3892 0.2722 0.8673 0.0590 0.340(8) Uiso DR . P . 4 . H621 H 0.4318 -0.0088 0.9184 0.0609 0.340(8) Uiso DR . P . 4 . H622 H 0.3461 0.0452 0.8988 0.0610 0.340(8) Uiso DR . P . 4 . H631 H 0.3969 0.0941 0.9864 0.0641 0.340(8) Uiso DR . P . 4 . H632 H 0.3748 0.2490 0.9559 0.0640 0.340(8) Uiso DR . P . 4 . H641 H 0.5235 0.1413 1.0013 0.0669 0.340(8) Uiso DR . P . 4 . H642 H 0.5021 0.2932 0.9687 0.0672 0.340(8) Uiso DR . P . 4 . H651 H 0.5260 0.3698 1.0520 0.0869 0.340(8) Uiso DR . P . 4 . H652 H 0.4779 0.2353 1.0644 0.0870 0.340(8) Uiso DR . P . 4 . H653 H 0.4370 0.3708 1.0297 0.0870 0.340(8) Uiso DR . P . 4 . H1081 H 1.1615 0.7956 0.6960 0.0551 1.0000 Uiso R . . . . . H1082 H 1.1911 0.6388 0.7195 0.0551 1.0000 Uiso R . . . . . H1083 H 1.1691 0.6614 0.6607 0.0551 1.0000 Uiso R . . . . . H1091 H 0.9682 0.9233 0.6982 0.0473 1.0000 Uiso R . . . . . H1092 H 1.0519 0.9418 0.6976 0.0469 1.0000 Uiso R . . . . . H1093 H 0.9858 0.9260 0.6462 0.0475 1.0000 Uiso R . . . . . H1101 H 1.1551 0.3755 0.7054 0.0328 1.0000 Uiso R . . . . . H1102 H 1.0847 0.2652 0.6957 0.0331 1.0000 Uiso R . . . . . H1111 H 1.1414 0.2430 0.6306 0.0572 1.0000 Uiso R . . . . . H1112 H 1.1261 0.4186 0.6165 0.0571 1.0000 Uiso R . . . . . H1121 H 1.0138 0.1987 0.6017 0.0581 1.0000 Uiso R . . . . . H1122 H 0.9992 0.3757 0.5889 0.0583 1.0000 Uiso R . . . . . H1131 H 1.0773 0.1860 0.5378 0.0729 1.0000 Uiso R . . . . . H1132 H 1.0622 0.3606 0.5261 0.0727 1.0000 Uiso R . . . . . H1141 H 0.9469 0.1397 0.5096 0.0990 1.0000 Uiso R . . . . . H1142 H 0.9322 0.3153 0.4967 0.0990 1.0000 Uiso R . . . . . H1151 H 0.9261 0.1659 0.4226 0.1758 1.0000 Uiso R . . . . . H1152 H 1.0127 0.1275 0.4466 0.1759 1.0000 Uiso R . . . . . H1153 H 0.9868 0.2958 0.4313 0.1760 1.0000 Uiso R . . . . . H1171 H 0.8575 0.7912 0.6081 0.0460 0.788(10) Uiso DR . P . 1 . H1172 H 0.7808 0.7326 0.6164 0.0462 0.788(10) Uiso DR . P . 1 . H1181 H 0.8807 0.5376 0.5856 0.0550 0.788(10) Uiso DR . P . 1 . H1182 H 0.7993 0.4917 0.5890 0.0549 0.788(10) Uiso DR . P . 1 . H1191 H 0.8195 0.7046 0.5171 0.0579 0.788(10) Uiso DR . P . 1 . H1192 H 0.8047 0.5296 0.5035 0.0580 0.788(10) Uiso DR . P . 1 . H1201 H 0.7008 0.7281 0.5259 0.0689 0.788(10) Uiso DR . P . 1 . H1202 H 0.6848 0.5529 0.5141 0.0689 0.788(10) Uiso DR . P . 1 . H1211 H 0.6264 0.6935 0.4410 0.0959 0.788(10) Uiso DR . P . 1 . H1212 H 0.7046 0.7690 0.4426 0.0959 0.788(10) Uiso DR . P . 1 . H1213 H 0.6909 0.5948 0.4305 0.0958 0.788(10) Uiso DR . P . 1 . H1671 H 0.8686 0.7388 0.6011 0.0460 0.212(10) Uiso DR . P . 2 . H1672 H 0.7956 0.7837 0.6171 0.0460 0.212(10) Uiso DR . P . 2 . H1681 H 0.8294 0.4927 0.5879 0.0519 0.212(10) Uiso DR . P . 2 . H1682 H 0.7637 0.5192 0.6134 0.0520 0.212(10) Uiso DR . P . 2 . H1691 H 0.7081 0.6882 0.5441 0.0610 0.212(10) Uiso DR . P . 2 . H1692 H 0.7051 0.5137 0.5289 0.0610 0.212(10) Uiso DR . P . 2 . H1701 H 0.8050 0.7247 0.5097 0.0690 0.212(10) Uiso DR . P . 2 . H1702 H 0.8042 0.5498 0.4953 0.0690 0.212(10) Uiso DR . P . 2 . H1711 H 0.7489 0.7062 0.4250 0.0970 0.212(10) Uiso DR . P . 2 . H1712 H 0.6836 0.7496 0.4484 0.0970 0.212(10) Uiso DR . P . 2 . H1713 H 0.6919 0.5813 0.4318 0.0970 0.212(10) Uiso DR . P . 2 . H1161 H 0.8743 0.7539 0.6954 0.0327 1.0000 Uiso R . . . . . H1162 H 0.8506 0.5808 0.6855 0.0332 1.0000 Uiso R . . . . . H2011 H 0.7381 0.1264 0.8113 0.0699 1.0000 Uiso R . . . . . H2012 H 0.7727 0.0485 0.7847 0.0697 1.0000 Uiso R . . . . . H2021 H 0.7265 0.4026 0.7166 0.0708 1.0000 Uiso R . . . . . H2022 H 0.7645 0.3264 0.6906 0.0711 1.0000 Uiso 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 Br1 0.0274(3) 0.0233(3) 0.0551(4) -0.0042(2) 0.0187(2) -0.00130(19) Br2 0.0234(2) 0.0223(2) 0.0305(3) 0.00058(19) 0.0074(2) -0.00176(18) C3 0.0249(19) 0.020(2) 0.023(2) -0.0013(19) 0.007(2) -0.0017(18) N4 0.0279(17) 0.0326(17) 0.021(2) 0.0000(17) 0.0072(17) -0.0085(13) C5 0.026(3) 0.026(2) 0.026(3) -0.002(2) 0.007(2) -0.0022(19) C6 0.025(2) 0.022(2) 0.026(3) -0.003(2) 0.006(2) -0.0048(19) N7 0.022(2) 0.023(2) 0.027(2) -0.0006(16) 0.0072(17) 0.0006(15) C8 0.026(3) 0.033(3) 0.061(4) -0.007(3) 0.016(3) -0.005(2) C9 0.032(3) 0.026(3) 0.048(3) -0.003(2) 0.015(3) -0.003(2) C10 0.0564(9) 0.0577(13) 0.0447(15) -0.0097(12) 0.0279(11) 0.0028(9) C11 0.0630(12) 0.0617(13) 0.0449(16) -0.0077(14) 0.0295(12) 0.0014(8) C12 0.0675(13) 0.0654(14) 0.0463(18) -0.0068(15) 0.0289(13) 0.0013(8) C13 0.0743(15) 0.0705(15) 0.0476(19) -0.0058(16) 0.0311(14) 0.0022(9) C14 0.0810(16) 0.0768(16) 0.050(2) -0.0058(17) 0.0299(15) 0.0014(10) C15 0.0918(17) 0.0880(17) 0.051(2) -0.0084(19) 0.0308(15) 0.0015(10) C16 0.025(2) 0.027(3) 0.029(3) -0.002(2) 0.010(2) 0.0009(19) C17 0.020(2) 0.032(3) 0.036(3) 0.000(2) 0.008(2) 0.005(2) C18 0.039(3) 0.033(3) 0.031(3) 0.001(2) 0.006(2) 0.001(2) C19 0.057(4) 0.040(3) 0.033(3) 0.001(3) -0.001(3) 0.008(3) C20 0.121(7) 0.033(3) 0.038(4) -0.001(3) -0.009(4) 0.002(4) C21 0.135(8) 0.043(4) 0.036(4) -0.003(3) -0.011(4) 0.006(4) C60 0.0564(9) 0.0577(13) 0.0447(15) -0.0097(12) 0.0279(11) 0.0028(9) C61 0.0592(9) 0.0611(14) 0.0454(17) -0.0106(13) 0.0280(14) 0.0015(10) C62 0.0625(10) 0.0635(16) 0.0462(19) -0.0102(14) 0.0287(16) 0.0015(9) C63 0.0695(13) 0.0671(17) 0.048(2) -0.0117(14) 0.0286(17) 0.0037(9) C64 0.0746(14) 0.0708(19) 0.050(2) -0.0130(15) 0.0271(18) 0.0033(8) C65 0.0838(14) 0.078(2) 0.053(2) -0.0183(15) 0.026(2) 0.0029(7) Br101 0.0260(3) 0.0228(2) 0.0483(3) -0.0013(2) 0.0167(2) -0.00035(19) Br102 0.0236(2) 0.0219(2) 0.0292(3) 0.00110(19) 0.0075(2) -0.00240(18) C103 0.026(2) 0.018(2) 0.016(2) -0.0006(18) 0.0052(19) -0.0056(18) N104 0.0200(19) 0.0200(19) 0.032(2) 0.0002(17) 0.0098(17) 0.0010(15) C105 0.021(2) 0.028(3) 0.030(3) 0.000(2) 0.008(2) 0.0003(19) C106 0.023(2) 0.024(2) 0.023(3) -0.0021(19) 0.008(2) -0.0054(19) N107 0.0191(19) 0.022(2) 0.024(2) 0.0002(16) 0.0085(16) 0.0005(15) C108 0.027(3) 0.030(3) 0.055(4) 0.001(3) 0.015(3) 0.000(2) C109 0.033(3) 0.020(2) 0.044(3) -0.004(2) 0.014(2) -0.001(2) C110 0.021(2) 0.023(2) 0.036(3) 0.003(2) 0.003(2) 0.0038(19) C111 0.048(4) 0.052(4) 0.045(4) -0.004(3) 0.016(3) 0.019(3) C112 0.049(4) 0.054(4) 0.055(4) -0.007(3) 0.023(3) 0.005(3) C113 0.074(5) 0.074(5) 0.043(4) -0.009(3) 0.024(4) 0.009(4) C114 0.097(6) 0.108(7) 0.046(5) 0.004(4) 0.026(4) 0.009(5) C115 0.147(10) 0.155(10) 0.043(5) -0.014(6) 0.024(6) -0.007(8) C116 0.019(2) 0.026(3) 0.039(3) -0.003(2) 0.010(2) -0.0009(19) C117 0.035(3) 0.031(3) 0.043(3) 0.004(2) 0.003(2) 0.006(2) C118 0.049(4) 0.036(4) 0.043(4) 0.001(3) 0.004(3) 0.007(3) C119 0.053(4) 0.044(4) 0.039(4) -0.005(3) 0.002(4) 0.000(3) C120 0.061(5) 0.050(4) 0.049(5) 0.006(3) -0.004(4) 0.002(3) C121 0.075(5) 0.055(5) 0.050(5) 0.006(4) -0.017(5) 0.004(5) C167 0.035(3) 0.031(3) 0.043(3) 0.004(2) 0.003(2) 0.006(2) C168 0.048(8) 0.040(7) 0.037(8) 0.002(6) 0.002(6) 0.004(5) C169 0.062(10) 0.052(8) 0.040(9) 0.001(8) -0.001(8) 0.006(6) C170 0.073(12) 0.064(9) 0.042(11) 0.007(9) 0.003(9) 0.010(6) C171 0.087(14) 0.079(11) 0.047(12) 0.013(11) -0.001(9) 0.009(7) O201 0.048(2) 0.036(2) 0.068(3) 0.006(2) 0.033(2) 0.0058(18) O202 0.048(2) 0.033(2) 0.069(3) 0.005(2) 0.027(2) 0.0048(18) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.13723(5) loop_ _geom_bond_atom_site_label_1 _geom_bond_site_symmetry_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag Br1 . Br2 . 3.1588(7) yes Br2 . C3 . 1.860(4) yes C3 . N4 . 1.329(6) yes C3 . N7 . 1.340(6) yes N4 . C5 . 1.397(6) yes N4 . C10 . 1.485(7) yes C5 . C6 . 1.360(6) yes C5 . C8 . 1.485(6) yes C6 . N7 . 1.397(6) yes C6 . C9 . 1.483(7) yes N7 . C16 . 1.477(6) yes C8 . H81 . 0.956 no C8 . H82 . 0.955 no C8 . H83 . 0.959 no C9 . H91 . 0.952 no C9 . H92 . 0.955 no C9 . H93 . 0.953 no C10 . C11 . 1.521(11) yes C10 . H101 . 0.968 no C10 . H102 . 0.970 no C11 . C12 . 1.482(15) yes C11 . H111 . 0.963 no C11 . H112 . 0.970 no C12 . C13 . 1.542(14) yes C12 . H121 . 0.971 no C12 . H122 . 0.972 no C13 . C14 . 1.505(16) yes C13 . H131 . 0.966 no C13 . H132 . 0.968 no C14 . C15 . 1.485(15) yes C14 . H141 . 0.969 no C14 . H142 . 0.975 no C15 . H151 . 0.965 no C15 . H152 . 0.964 no C15 . H153 . 0.962 no C16 . C17 . 1.519(7) yes C16 . H161 . 0.965 no C16 . H162 . 0.963 no C17 . C18 . 1.524(7) yes C17 . H171 . 0.966 no C17 . H172 . 0.968 no C18 . C19 . 1.530(7) yes C18 . H181 . 0.960 no C18 . H182 . 0.964 no C19 . C20 . 1.518(8) yes C19 . H191 . 0.971 no C19 . H192 . 0.970 no C20 . C21 . 1.538(9) yes C20 . H201 . 0.970 no C20 . H202 . 0.965 no C21 . H211 . 0.955 no C21 . H212 . 0.965 no C21 . H213 . 0.958 no C60 . C61 . 1.54(2) yes C60 . H601 . 0.969 no C60 . H602 . 0.969 no C61 . C62 . 1.55(3) yes C61 . H611 . 0.971 no C61 . H612 . 0.969 no C62 . C63 . 1.55(3) yes C62 . H621 . 0.969 no C62 . H622 . 0.965 no C63 . C64 . 1.48(3) yes C63 . H631 . 0.971 no C63 . H632 . 0.970 no C64 . C65 . 1.518(10) yes C64 . H641 . 0.970 no C64 . H642 . 0.972 no C65 . H651 . 0.964 no C65 . H652 . 0.962 no C65 . H653 . 0.962 no Br101 . Br102 . 3.1579(6) yes Br102 . C103 . 1.860(4) yes C103 . N104 . 1.333(6) yes C103 . N107 . 1.333(6) yes N104 . C105 . 1.399(6) yes N104 . C110 . 1.478(6) yes C105 . C106 . 1.352(6) yes C105 . C108 . 1.494(6) yes C106 . N107 . 1.386(5) yes C106 . C109 . 1.497(6) yes N107 . C116 . 1.487(5) yes C108 . H1081 . 0.954 no C108 . H1082 . 0.952 no C108 . H1083 . 0.953 no C109 . H1091 . 0.954 no C109 . H1092 . 0.954 no C109 . H1093 . 0.958 no C110 . C111 . 1.521(7) yes C110 . H1101 . 0.966 no C110 . H1102 . 0.971 no C111 . C112 . 1.462(8) yes C111 . H1111 . 0.969 no C111 . H1112 . 0.977 no C112 . C113 . 1.539(8) yes C112 . H1121 . 0.982 no C112 . H1122 . 0.980 no C113 . C114 . 1.492(10) yes C113 . H1131 . 0.971 no C113 . H1132 . 0.969 no C114 . C115 . 1.524(11) yes C114 . H1141 . 0.974 no C114 . H1142 . 0.971 no C115 . H1151 . 0.960 no C115 . H1152 . 0.963 no C115 . H1153 . 0.959 no C116 . C117 . 1.536(7) yes C116 . H1161 . 0.966 no C116 . H1162 . 0.965 no C117 . C118 . 1.530(7) yes C117 . H1171 . 0.976 no C117 . H1172 . 0.973 no C118 . C119 . 1.518(8) yes C118 . H1181 . 0.972 no C118 . H1182 . 0.970 no C119 . C120 . 1.495(8) yes C119 . H1191 . 0.972 no C119 . H1192 . 0.974 no C120 . C121 . 1.515(8) yes C120 . H1201 . 0.971 no C120 . H1202 . 0.970 no C121 . H1211 . 0.960 no C121 . H1212 . 0.963 no C121 . H1213 . 0.960 no C167 . C168 . 1.501(10) yes C167 . H1671 . 0.970 no C167 . H1672 . 0.970 no C168 . C169 . 1.501(10) yes C168 . H1681 . 0.970 no C168 . H1682 . 0.969 no C169 . C170 . 1.499(10) yes C169 . H1691 . 0.970 no C169 . H1692 . 0.970 no C170 . C171 . 1.501(10) yes C170 . H1701 . 0.970 no C170 . H1702 . 0.970 no C171 . H1711 . 0.960 no C171 . H1712 . 0.960 no C171 . H1713 . 0.960 no O201 . H2011 . 0.819 no O201 . H2012 . 0.817 no O202 . H2021 . 0.820 no O202 . H2022 . 0.822 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C3 . Br2 . Br1 . 168.15(14) yes Br2 . C3 . N4 . 126.5(3) yes Br2 . C3 . N7 . 124.1(3) yes N4 . C3 . N7 . 109.2(4) yes C3 . N4 . C5 . 108.7(4) yes C3 . N4 . C10 . 125.3(4) yes C5 . N4 . C10 . 126.0(4) yes N4 . C5 . C6 . 106.8(4) yes N4 . C5 . C8 . 123.0(4) yes C6 . C5 . C8 . 130.2(4) yes C5 . C6 . N7 . 107.1(4) yes C5 . C6 . C9 . 129.7(4) yes N7 . C6 . C9 . 123.1(4) yes C6 . N7 . C3 . 108.2(4) yes C6 . N7 . C16 . 125.5(4) yes C3 . N7 . C16 . 126.3(4) yes C5 . C8 . H81 . 109.9 no C5 . C8 . H82 . 110.0 no H81 . C8 . H82 . 108.6 no C5 . C8 . H83 . 110.6 no H81 . C8 . H83 . 108.8 no H82 . C8 . H83 . 108.8 no C6 . C9 . H91 . 111.1 no C6 . C9 . H92 . 110.8 no H91 . C9 . H92 . 108.4 no C6 . C9 . H93 . 108.9 no H91 . C9 . H93 . 109.0 no H92 . C9 . H93 . 108.6 no N4 . C10 . C11 . 112.0(6) yes N4 . C10 . H101 . 108.9 no C11 . C10 . H101 . 109.3 no N4 . C10 . H102 . 108.5 no C11 . C10 . H102 . 108.8 no H101 . C10 . H102 . 109.3 no C10 . C11 . C12 . 114.8(8) yes C10 . C11 . H111 . 109.2 no C12 . C11 . H111 . 107.3 no C10 . C11 . H112 . 107.9 no C12 . C11 . H112 . 108.5 no H111 . C11 . H112 . 108.9 no C11 . C12 . C13 . 113.0(9) yes C11 . C12 . H121 . 109.1 no C13 . C12 . H121 . 108.6 no C11 . C12 . H122 . 108.5 no C13 . C12 . H122 . 108.9 no H121 . C12 . H122 . 108.6 no C12 . C13 . C14 . 113.6(9) yes C12 . C13 . H131 . 107.4 no C14 . C13 . H131 . 107.6 no C12 . C13 . H132 . 109.8 no C14 . C13 . H132 . 108.3 no H131 . C13 . H132 . 110.1 no C13 . C14 . C15 . 113.3(10) yes C13 . C14 . H141 . 108.3 no C15 . C14 . H141 . 109.9 no C13 . C14 . H142 . 108.7 no C15 . C14 . H142 . 107.2 no H141 . C14 . H142 . 109.3 no C14 . C15 . H151 . 108.3 no C14 . C15 . H152 . 108.3 no H151 . C15 . H152 . 110.0 no C14 . C15 . H153 . 110.9 no H151 . C15 . H153 . 109.2 no H152 . C15 . H153 . 110.0 no N7 . C16 . C17 . 112.2(4) yes N7 . C16 . H161 . 107.8 no C17 . C16 . H161 . 109.1 no N7 . C16 . H162 . 109.8 no C17 . C16 . H162 . 108.7 no H161 . C16 . H162 . 109.3 no C16 . C17 . C18 . 114.8(4) yes C16 . C17 . H171 . 108.1 no C18 . C17 . H171 . 109.4 no C16 . C17 . H172 . 107.6 no C18 . C17 . H172 . 107.9 no H171 . C17 . H172 . 108.9 no C17 . C18 . C19 . 110.8(4) yes C17 . C18 . H181 . 109.8 no C19 . C18 . H181 . 109.5 no C17 . C18 . H182 . 108.7 no C19 . C18 . H182 . 109.6 no H181 . C18 . H182 . 108.4 no C18 . C19 . C20 . 113.4(5) yes C18 . C19 . H191 . 108.3 no C20 . C19 . H191 . 108.6 no C18 . C19 . H192 . 109.2 no C20 . C19 . H192 . 108.2 no H191 . C19 . H192 . 109.2 no C19 . C20 . C21 . 111.3(5) yes C19 . C20 . H201 . 108.6 no C21 . C20 . H201 . 109.6 no C19 . C20 . H202 . 109.6 no C21 . C20 . H202 . 109.1 no H201 . C20 . H202 . 108.7 no C20 . C21 . H211 . 110.0 no C20 . C21 . H212 . 109.1 no H211 . C21 . H212 . 109.3 no C20 . C21 . H213 . 109.3 no H211 . C21 . H213 . 109.9 no H212 . C21 . H213 . 109.3 no N4 . C60 . C61 . 112.0(9) yes N4 . C60 . H601 . 108.9 no C61 . C60 . H601 . 109.1 no N4 . C60 . H602 . 108.3 no C61 . C60 . H602 . 108.8 no H601 . C60 . H602 . 109.7 no C60 . C61 . C62 . 111.9(16) yes C60 . C61 . H611 . 109.3 no C62 . C61 . H611 . 109.5 no C60 . C61 . H612 . 108.8 no C62 . C61 . H612 . 108.0 no H611 . C61 . H612 . 109.3 no C61 . C62 . C63 . 112.7(17) yes C61 . C62 . H621 . 108.1 no C63 . C62 . H621 . 107.9 no C61 . C62 . H622 . 108.7 no C63 . C62 . H622 . 109.9 no H621 . C62 . H622 . 109.5 no C62 . C63 . C64 . 119.8(17) yes C62 . C63 . H631 . 106.7 no C64 . C63 . H631 . 105.7 no C62 . C63 . H632 . 106.4 no C64 . C63 . H632 . 108.6 no H631 . C63 . H632 . 109.4 no C63 . C64 . C65 . 108.6(18) yes C63 . C64 . H641 . 111.5 no C65 . C64 . H641 . 109.6 no C63 . C64 . H642 . 107.8 no C65 . C64 . H642 . 109.6 no H641 . C64 . H642 . 109.7 no C64 . C65 . H651 . 109.8 no C64 . C65 . H652 . 109.9 no H651 . C65 . H652 . 109.6 no C64 . C65 . H653 . 109.5 no H651 . C65 . H653 . 109.0 no H652 . C65 . H653 . 109.0 no C103 . Br102 . Br101 . 168.20(14) yes Br102 . C103 . N104 . 126.0(3) yes Br102 . C103 . N107 . 124.9(3) yes N104 . C103 . N107 . 108.9(4) yes C103 . N104 . C105 . 108.0(4) yes C103 . N104 . C110 . 126.2(4) yes C105 . N104 . C110 . 125.5(4) yes N104 . C105 . C106 . 107.3(4) yes N104 . C105 . C108 . 122.5(4) yes C106 . C105 . C108 . 130.1(4) yes C105 . C106 . N107 . 106.8(4) yes C105 . C106 . C109 . 129.9(4) yes N107 . C106 . C109 . 123.3(4) yes C106 . N107 . C103 . 109.0(4) yes C106 . N107 . C116 . 125.7(4) yes C103 . N107 . C116 . 125.2(4) yes C105 . C108 . H1081 . 110.1 no C105 . C108 . H1082 . 109.9 no H1081 . C108 . H1082 . 108.6 no C105 . C108 . H1083 . 110.3 no H1081 . C108 . H1083 . 109.3 no H1082 . C108 . H1083 . 108.5 no C106 . C109 . H1091 . 110.3 no C106 . C109 . H1092 . 109.6 no H1091 . C109 . H1092 . 109.4 no C106 . C109 . H1093 . 109.5 no H1091 . C109 . H1093 . 108.3 no H1092 . C109 . H1093 . 109.8 no N104 . C110 . C111 . 111.5(4) yes N104 . C110 . H1101 . 108.5 no C111 . C110 . H1101 . 109.4 no N104 . C110 . H1102 . 109.2 no C111 . C110 . H1102 . 109.3 no H1101 . C110 . H1102 . 109.0 no C110 . C111 . C112 . 116.4(5) yes C110 . C111 . H1111 . 106.8 no C112 . C111 . H1111 . 108.1 no C110 . C111 . H1112 . 109.2 no C112 . C111 . H1112 . 106.1 no H1111 . C111 . H1112 . 110.2 no C111 . C112 . C113 . 113.2(5) yes C111 . C112 . H1121 . 108.4 no C113 . C112 . H1121 . 110.0 no C111 . C112 . H1122 . 108.6 no C113 . C112 . H1122 . 107.3 no H1121 . C112 . H1122 . 109.2 no C112 . C113 . C114 . 112.0(6) yes C112 . C113 . H1131 . 108.0 no C114 . C113 . H1131 . 109.5 no C112 . C113 . H1132 . 108.9 no C114 . C113 . H1132 . 109.8 no H1131 . C113 . H1132 . 108.5 no C113 . C114 . C115 . 112.5(7) yes C113 . C114 . H1141 . 108.5 no C115 . C114 . H1141 . 108.5 no C113 . C114 . H1142 . 108.7 no C115 . C114 . H1142 . 109.1 no H1141 . C114 . H1142 . 109.5 no C114 . C115 . H1151 . 109.6 no C114 . C115 . H1152 . 109.7 no H1151 . C115 . H1152 . 109.3 no C114 . C115 . H1153 . 109.0 no H1151 . C115 . H1153 . 109.4 no H1152 . C115 . H1153 . 109.8 no N107 . C116 . C117 . 111.6(4) yes N107 . C116 . H1161 . 108.4 no C117 . C116 . H1161 . 108.8 no N107 . C116 . H1162 . 108.1 no C117 . C116 . H1162 . 109.7 no H1161 . C116 . H1162 . 110.1 no C116 . C117 . C118 . 114.4(4) yes C116 . C117 . H1171 . 108.3 no C118 . C117 . H1171 . 109.1 no C116 . C117 . H1172 . 107.8 no C118 . C117 . H1172 . 108.4 no H1171 . C117 . H1172 . 108.7 no C117 . C118 . C119 . 115.5(6) yes C117 . C118 . H1181 . 107.7 no C119 . C118 . H1181 . 107.9 no C117 . C118 . H1182 . 108.0 no C119 . C118 . H1182 . 108.6 no H1181 . C118 . H1182 . 109.1 no C118 . C119 . C120 . 115.9(7) yes C118 . C119 . H1191 . 108.4 no C120 . C119 . H1191 . 107.1 no C118 . C119 . H1192 . 108.9 no C120 . C119 . H1192 . 107.2 no H1191 . C119 . H1192 . 109.2 no C119 . C120 . C121 . 113.3(8) yes C119 . C120 . H1201 . 108.0 no C121 . C120 . H1201 . 108.2 no C119 . C120 . H1202 . 109.1 no C121 . C120 . H1202 . 108.9 no H1201 . C120 . H1202 . 109.2 no C120 . C121 . H1211 . 109.4 no C120 . C121 . H1212 . 109.6 no H1211 . C121 . H1212 . 109.8 no C120 . C121 . H1213 . 109.4 no H1211 . C121 . H1213 . 109.2 no H1212 . C121 . H1213 . 109.4 no C116 . C167 . C168 . 109.1(10) yes C116 . C167 . H1671 . 109.6 no C168 . C167 . H1671 . 110.3 no C116 . C167 . H1672 . 109.4 no C168 . C167 . H1672 . 109.1 no H1671 . C167 . H1672 . 109.4 no C167 . C168 . C169 . 111.5(18) yes C167 . C168 . H1681 . 108.3 no C169 . C168 . H1681 . 108.4 no C167 . C168 . H1682 . 109.4 no C169 . C168 . H1682 . 109.6 no H1681 . C168 . H1682 . 109.5 no C168 . C169 . C170 . 117(3) yes C168 . C169 . H1691 . 107.4 no C170 . C169 . H1691 . 108.2 no C168 . C169 . H1692 . 107.6 no C170 . C169 . H1692 . 107.0 no H1691 . C169 . H1692 . 109.6 no C169 . C170 . C171 . 117(3) yes C169 . C170 . H1701 . 106.3 no C171 . C170 . H1701 . 107.4 no C169 . C170 . H1702 . 107.9 no C171 . C170 . H1702 . 108.7 no H1701 . C170 . H1702 . 109.6 no C170 . C171 . H1711 . 107.9 no C170 . C171 . H1712 . 111.4 no H1711 . C171 . H1712 . 109.2 no C170 . C171 . H1713 . 109.6 no H1711 . C171 . H1713 . 109.4 no H1712 . C171 . H1713 . 109.4 no H2011 . O201 . H2012 . 104.7 no H2021 . O202 . H2022 . 106.9 no loop_ _geom_hbond_atom_site_label_D _geom_hbond_site_symmetry_D _geom_hbond_atom_site_label_H _geom_hbond_site_symmetry_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_angle_DHA _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_publ_flag C16 . H161 . O201 . 155.68(14) 0.965 2.525 3.428(16) yes C14 . H642 . C12 . 133(2) 0.876 1.874 2.549(16) yes C168 . H1682 . O202 . 156.6(6) 0.969 2.490 3.401(16) yes C116 . H1162 . O202 . 158.72(14) 0.965 2.519 3.436(16) yes _iucr_refine_instruction_details_constraints ; # # Punched on 26/06/12 at 14:27:00 # #LIST 12 BLOCK SCALE X'S, U'S EQUIV PART(0001,OCC) PART(0002,OCC) WEIGHT -1 PART(0001,OCC) EQUIV PART(0003,OCC) PART(0004,OCC) WEIGHT -1 PART(0003,OCC) RIDE C(10,U'S) C(60,U'S) RIDE C(117,U'S) C(167,U'S) RIDE C ( 8,X'S) H ( 81,X'S) H ( 82,X'S) H ( 83,X'S) RIDE C ( 9,X'S) H ( 93,X'S) H ( 92,X'S) H ( 91,X'S) RIDE C ( 10,X'S) H ( 101,X'S) H ( 102,X'S) CONT C ( 60,X'S) H ( 601,X'S) H ( 602,X'S) RIDE C ( 11,X'S) H ( 111,X'S) H ( 112,X'S) RIDE C ( 12,X'S) H ( 121,X'S) H ( 122,X'S) RIDE C ( 13,X'S) H ( 131,X'S) H ( 132,X'S) RIDE C ( 14,X'S) H ( 141,X'S) H ( 142,X'S) RIDE C ( 15,X'S) H ( 153,X'S) H ( 152,X'S) H ( 151,X'S) RIDE C ( 16,X'S) H ( 161,X'S) H ( 162,X'S) RIDE C ( 17,X'S) H ( 171,X'S) H ( 172,X'S) RIDE C ( 18,X'S) H ( 181,X'S) H ( 182,X'S) RIDE C ( 19,X'S) H ( 191,X'S) H ( 192,X'S) RIDE C ( 20,X'S) H ( 201,X'S) H ( 202,X'S) RIDE C ( 21,X'S) H ( 211,X'S) H ( 212,X'S) H ( 213,X'S) RIDE C ( 61,X'S) H ( 611,X'S) H ( 612,X'S) RIDE C ( 62,X'S) H ( 621,X'S) H ( 622,X'S) RIDE C ( 63,X'S) H ( 631,X'S) H ( 632,X'S) RIDE C ( 64,X'S) H ( 641,X'S) H ( 642,X'S) RIDE C ( 65,X'S) H ( 651,X'S) H ( 652,X'S) H ( 653,X'S) RIDE C ( 108,X'S) H (1083,X'S) H (1082,X'S) H (1081,X'S) RIDE C ( 109,X'S) H (1091,X'S) H (1092,X'S) H (1093,X'S) RIDE C ( 110,X'S) H (1101,X'S) H (1102,X'S) RIDE C ( 111,X'S) H (1111,X'S) H (1112,X'S) RIDE C ( 112,X'S) H (1121,X'S) H (1122,X'S) RIDE C ( 113,X'S) H (1131,X'S) H (1132,X'S) RIDE C ( 114,X'S) H (1141,X'S) H (1142,X'S) RIDE C ( 115,X'S) H (1153,X'S) H (1152,X'S) H (1151,X'S) RIDE C ( 116,X'S) H (1161,X'S) H (1162,X'S) RIDE C ( 117,X'S) H (1171,X'S) H (1172,X'S) CONT C ( 167,X'S) H (1671,X'S) H (1672,X'S) RIDE C ( 118,X'S) H (1181,X'S) H (1182,X'S) RIDE C ( 119,X'S) H (1191,X'S) H (1192,X'S) RIDE C ( 120,X'S) H (1201,X'S) H (1202,X'S) RIDE C ( 121,X'S) H (1213,X'S) H (1212,X'S) H (1211,X'S) RIDE C ( 168,X'S) H (1681,X'S) H (1682,X'S) RIDE C ( 169,X'S) H (1691,X'S) H (1692,X'S) RIDE C ( 170,X'S) H (1701,X'S) H (1702,X'S) RIDE C ( 171,X'S) H (1711,X'S) H (1712,X'S) H (1713,X'S) RIDE O ( 201,X'S) H (2012,X'S) H (2011,X'S) RIDE O ( 202,X'S) H (2022,X'S) H (2021,X'S) END ; _iucr_refine_instruction_details_restraints ; # # Punched on 26/06/12 at 14:27:00 # #LIST 16 DIST 1.5,0.01 = C(117) TO C(118) C(118) TO C(119) C(119) TO C(120) CONT C(120) TO C(121) CONT C(117) TO C(168) C(168) TO C(169) C(169) TO C(170) C(170) TO C(171) CONT C(64) TO C(65) DELU 0.01,0.001 PART(0001) AND PART(0002) SIMU 0.01,0.001 PART(0001) AND PART(0002) DELU 0.001,0.001 PART(0003) AND PART(0004) SIMU 0.001,0.001 PART(0003) AND PART(0004) REM HREST START (DO NOT REMOVE THIS LINE) REM HREST END (DO NOT REMOVE THIS LINE) REM DELU START (DO NOT REMOVE THIS LINE) VIBR .0, 0.00200 = C(3) TO N(4) VIBR .0, 0.00200 = N(4) TO C(5) VIBR .0, 0.00200 = N(4) TO C(10) VIBR .0, 0.00200 = N(4) TO C(60) REM DELU END (DO NOT REMOVE THIS LINE) REM THERMSIM START (DO NOT REMOVE THIS LINE) U(IJ) .0, 0.04000 = C(3) TO N(4) U(IJ) .0, 0.04000 = N(4) TO C(5) U(IJ) .0, 0.04000 = N(4) TO C(10) U(IJ) .0, 0.04000 = N(4) TO C(60) REM THERMSIM END (DO NOT REMOVE THIS LINE) END ;