# Electronic Supplementary Material (ESI) for Chemical Communications # This journal is © The Royal Society of Chemistry 2013 ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_19.HBF4 _ccdc_journal_depnumber ? #============================================================================== _cell_length_a 9.33249(10) _cell_length_b 15.31121(15) _cell_length_c 20.0967(2) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 2871.65(5) _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P 21 21 21' _symmetry_space_group_name_Hall 'P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz x,y,z x+1/2,-y+1/2,-z -x,y+1/2,-z+1/2 -x+1/2,-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 0.0181 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' B 0.0090 0.0039 2.0545 23.2185 1.3326 1.0210 1.0979 60.3498 0.7068 0.1403 -0.1932 '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' 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' F 0.0727 0.0534 3.5392 10.2825 2.6412 4.2944 1.5170 0.2615 1.0243 26.1476 0.2776 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 4 # Given Formula = C31 H36 B1 F4 N1 O2 # Dc = 1.25 Fooo = 1144.00 Mu = 7.84 M = 541.44 # Found Formula = C31 H36 B1 F4 N1 O2 # Dc = 1.25 FOOO = 1144.00 Mu = 7.84 M = 541.43 _chemical_formula_sum 'C31 H36 B1 F4 N1 O2' _chemical_formula_moiety 'C31 H36 B1 F4 N1 O2' _chemical_compound_source . _chemical_formula_weight 541.43 _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _cell_measurement_temperature 150 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_min 0.230 _exptl_crystal_size_mid 0.260 _exptl_crystal_size_max 0.300 _exptl_crystal_density_diffrn 1.252 _exptl_crystal_density_meas . _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 1144 _exptl_absorpt_coefficient_mu 0.784 # Sheldrick geometric approximatio 0.82 0.84 _exptl_absorpt_correction_type none _diffrn_measurement_device_type Unknown _diffrn_measurement_device Serial _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54184 _diffrn_measurement_method \w/2\q # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'USER DEFINED DATA COLLECTION' _computing_cell_refinement 'USER DEFINED CELL REFINEMENT' _computing_data_reduction 'USER DEFINED DATA REDUCTION' _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 30050 _reflns_number_total 6010 _diffrn_reflns_av_R_equivalents 0.030 # Number of reflections without Friedels Law is 6010 # Number of reflections with Friedels Law is 3401 # Theoretical number of reflections is about 3024 _diffrn_reflns_theta_min 3.629 _diffrn_reflns_theta_max 76.671 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 76.671 _diffrn_measured_fraction_theta_full 0.999 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 11 _diffrn_reflns_limit_k_min -19 _diffrn_reflns_limit_k_max 19 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 25 _reflns_limit_h_min -11 _reflns_limit_h_max 11 _reflns_limit_k_min 0 _reflns_limit_k_max 19 _reflns_limit_l_min 0 _reflns_limit_l_max 25 _oxford_diffrn_Wilson_B_factor 2.94 _oxford_diffrn_Wilson_scale 0.05 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_diff_density_min -0.25 _refine_diff_density_max 0.23 # 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 5068 _refine_ls_number_restraints 0 _refine_ls_number_parameters 353 _oxford_refine_ls_R_factor_ref 0.0377 _refine_ls_wR_factor_ref 0.1017 _refine_ls_goodness_of_fit_ref 1.0101 _refine_ls_shift/su_max 0.0002611 _refine_ls_shift/su_mean 0.0000284 # The values computed with all filters except I/sigma _oxford_reflns_number_all 5261 _refine_ls_R_factor_all 0.0391 _refine_ls_wR_factor_all 0.1035 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 5140 _refine_ls_R_factor_gt 0.0382 _refine_ls_wR_factor_gt 0.1027 _refine_ls_abs_structure_Flack -0.03(14) _refine_ls_abs_structure_details 'Flack (1983), 2609 Friedel-pairs' # 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 ad _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^) + ( 0.06P)^2^ + 0.64P] ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 ; # 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 F1 F 0.68835(18) 0.50314(9) 0.31362(10) 0.0784 1.0000 Uani . . . . . . B2 B 0.6670(2) 0.41577(14) 0.30660(12) 0.0427 1.0000 Uani . . . . . . F3 F 0.67219(19) 0.37094(13) 0.36536(8) 0.0811 1.0000 Uani . . . . . . F4 F 0.53572(18) 0.40089(12) 0.27798(10) 0.0881 1.0000 Uani . . . . . . F5 F 0.7747(2) 0.38309(10) 0.26614(10) 0.0883 1.0000 Uani . . . . . . O6 O 0.30218(14) 0.33503(8) 0.13451(7) 0.0420 1.0000 Uani . . . . . . C7 C 0.33793(18) 0.40855(10) 0.10402(8) 0.0311 1.0000 Uani . . . . . . O8 O 0.25121(13) 0.45785(8) 0.07930(7) 0.0395 1.0000 Uani . . . . . . C9 C 0.49771(17) 0.42163(10) 0.10261(7) 0.0260 1.0000 Uani . . . . . . C10 C 0.54310(16) 0.51674(10) 0.08673(7) 0.0263 1.0000 Uani . . . . . . N11 N 0.44266(15) 0.58460(8) 0.11652(6) 0.0273 1.0000 Uani . . . . . . C12 C 0.46017(18) 0.67223(10) 0.08192(8) 0.0321 1.0000 Uani . . . . . . C13 C 0.40845(18) 0.66700(10) 0.01096(8) 0.0309 1.0000 Uani . . . . . . C14 C 0.26259(19) 0.66016(12) -0.00143(10) 0.0376 1.0000 Uani . . . . . . C15 C 0.2108(2) 0.65254(12) -0.06550(11) 0.0456 1.0000 Uani . . . . . . C16 C 0.3065(3) 0.65308(13) -0.11844(10) 0.0497 1.0000 Uani . . . . . . C17 C 0.4516(2) 0.66068(13) -0.10684(9) 0.0444 1.0000 Uani . . . . . . C18 C 0.50312(19) 0.66760(11) -0.04249(9) 0.0359 1.0000 Uani . . . . . . C19 C 0.44236(19) 0.58925(10) 0.19362(8) 0.0312 1.0000 Uani . . . . . . C20 C 0.5388(2) 0.66166(12) 0.22043(9) 0.0409 1.0000 Uani . . . . . . C21 C 0.28728(19) 0.59473(11) 0.21550(8) 0.0326 1.0000 Uani . . . . . . C22 C 0.2184(2) 0.51891(12) 0.23670(8) 0.0357 1.0000 Uani . . . . . . C23 C 0.0754(2) 0.52085(13) 0.25524(8) 0.0412 1.0000 Uani . . . . . . C24 C 0.0002(2) 0.59832(16) 0.25354(9) 0.0470 1.0000 Uani . . . . . . C25 C 0.0678(2) 0.67427(15) 0.23371(10) 0.0505 1.0000 Uani . . . . . . C26 C 0.2109(2) 0.67230(13) 0.21462(9) 0.0430 1.0000 Uani . . . . . . C27 C 0.69634(17) 0.53264(11) 0.10498(8) 0.0308 1.0000 Uani . . . . . . C28 C 0.79150(18) 0.55876(11) 0.06020(9) 0.0349 1.0000 Uani . . . . . . C29 C 0.9471(2) 0.57430(14) 0.07366(11) 0.0480 1.0000 Uani . . . . . . C30 C 0.56401(17) 0.36362(10) 0.04553(7) 0.0281 1.0000 Uani . . . . . . C31 C 0.56677(18) 0.26698(10) 0.06302(8) 0.0300 1.0000 Uani . . . . . . C32 C 0.6751(2) 0.23625(12) 0.10416(9) 0.0368 1.0000 Uani . . . . . . C33 C 0.6845(3) 0.14755(14) 0.11987(10) 0.0489 1.0000 Uani . . . . . . C34 C 0.5852(3) 0.09001(13) 0.09544(12) 0.0559 1.0000 Uani . . . . . . C35 C 0.4780(3) 0.11957(14) 0.05556(14) 0.0622 1.0000 Uani . . . . . . C36 C 0.4675(2) 0.20778(13) 0.03866(12) 0.0486 1.0000 Uani . . . . . . C37 C 0.4923(2) 0.38311(12) -0.01988(8) 0.0398 1.0000 Uani . . . . . . C38 C 0.5577(3) 0.42010(15) -0.07067(10) 0.0597 1.0000 Uani . . . . . . C39 C 0.1511(3) 0.31262(16) 0.13373(14) 0.0599 1.0000 Uani . . . . . . H91 H 0.5406 0.3997 0.1475 0.0262 1.0000 Uiso R . . . . . H101 H 0.5392 0.5193 0.0364 0.0280 1.0000 Uiso R . . . . . H122 H 0.5667 0.6859 0.0839 0.0272 1.0000 Uiso R . . . . . H121 H 0.4021 0.7143 0.1034 0.0285 1.0000 Uiso R . . . . . H191 H 0.4804 0.5363 0.2090 0.0340 1.0000 Uiso R . . . . . H201 H 0.5577 0.6510 0.2712 0.0603 1.0000 Uiso R . . . . . H202 H 0.6323 0.6489 0.1918 0.0593 1.0000 Uiso R . . . . . H203 H 0.4932 0.7214 0.2061 0.0621 1.0000 Uiso R . . . . . H221 H 0.2744 0.4673 0.2345 0.0371 1.0000 Uiso R . . . . . H231 H 0.0290 0.4725 0.2696 0.0419 1.0000 Uiso R . . . . . H241 H -0.0941 0.5991 0.2668 0.0608 1.0000 Uiso R . . . . . H251 H 0.0103 0.7257 0.2292 0.0598 1.0000 Uiso R . . . . . H261 H 0.2562 0.7228 0.1975 0.0466 1.0000 Uiso R . . . . . H292 H 0.9645 0.6315 0.0510 0.0569 1.0000 Uiso R . . . . . H293 H 0.9583 0.5848 0.1237 0.0594 1.0000 Uiso R . . . . . H291 H 1.0083 0.5238 0.0517 0.0583 1.0000 Uiso R . . . . . H301 H 0.6642 0.3786 0.0388 0.0291 1.0000 Uiso R . . . . . H331 H 0.7626 0.1254 0.1512 0.0669 1.0000 Uiso R . . . . . H341 H 0.5945 0.0310 0.1068 0.0722 1.0000 Uiso R . . . . . H351 H 0.3992 0.0820 0.0369 0.0634 1.0000 Uiso R . . . . . H371 H 0.3898 0.3646 -0.0231 0.0424 1.0000 Uiso R . . . . . H381 H 0.6550 0.4350 -0.0676 0.0690 1.0000 Uiso R . . . . . H382 H 0.5092 0.4264 -0.1151 0.0691 1.0000 Uiso R . . . . . H392 H 0.1307 0.2520 0.1551 0.0802 1.0000 Uiso R . . . . . H393 H 0.1117 0.3201 0.0874 0.0798 1.0000 Uiso R . . . . . H391 H 0.1014 0.3592 0.1633 0.0789 1.0000 Uiso R . . . . . H181 H 0.6035 0.6705 -0.0320 0.0345 1.0000 Uiso R . . . . . H171 H 0.5182 0.6615 -0.1435 0.0544 1.0000 Uiso R . . . . . H161 H 0.2707 0.6487 -0.1643 0.0517 1.0000 Uiso R . . . . . H151 H 0.1138 0.6441 -0.0717 0.0543 1.0000 Uiso R . . . . . H141 H 0.2009 0.6618 0.0322 0.0368 1.0000 Uiso R . . . . . H281 H 0.7615 0.5673 0.0117 0.0474 1.0000 Uiso R . . . . . H271 H 0.7233 0.5223 0.1513 0.0321 1.0000 Uiso R . . . . . H321 H 0.7476 0.2730 0.1219 0.0432 1.0000 Uiso R . . . . . H361 H 0.3819 0.2263 0.0130 0.0491 1.0000 Uiso R . . . . . H111 H 0.3633 0.5706 0.1107 0.0361 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 F1 0.0831(11) 0.0398(7) 0.1123(13) -0.0134(8) 0.0168(10) -0.0072(7) B2 0.0448(11) 0.0333(10) 0.0499(12) 0.0043(9) -0.0038(10) 0.0000(9) F3 0.0796(10) 0.0976(12) 0.0662(9) 0.0330(9) -0.0086(8) -0.0057(9) F4 0.0708(10) 0.0869(11) 0.1066(13) 0.0158(10) -0.0386(9) -0.0166(8) F5 0.0966(12) 0.0546(8) 0.1137(13) -0.0010(9) 0.0466(11) 0.0052(8) O6 0.0450(7) 0.0301(6) 0.0509(7) -0.0008(6) 0.0137(6) -0.0107(6) C7 0.0342(8) 0.0279(8) 0.0310(8) -0.0073(6) 0.0050(7) -0.0044(7) O8 0.0289(6) 0.0384(7) 0.0512(7) -0.0021(6) -0.0023(5) -0.0022(5) C9 0.0297(7) 0.0243(7) 0.0240(7) -0.0004(6) 0.0000(6) -0.0005(6) C10 0.0273(7) 0.0259(7) 0.0256(7) -0.0008(6) 0.0038(6) -0.0006(6) N11 0.0274(6) 0.0246(6) 0.0300(6) 0.0000(5) 0.0043(5) -0.0014(5) C12 0.0373(8) 0.0237(7) 0.0352(8) 0.0015(6) 0.0068(7) -0.0017(6) C13 0.0351(8) 0.0218(7) 0.0358(8) 0.0037(6) 0.0052(7) -0.0003(6) C14 0.0343(8) 0.0301(8) 0.0482(10) 0.0054(8) 0.0052(7) 0.0025(7) C15 0.0427(9) 0.0318(9) 0.0623(12) 0.0028(8) -0.0116(9) 0.0049(8) C16 0.0716(14) 0.0361(10) 0.0413(10) 0.0027(8) -0.0138(9) 0.0091(10) C17 0.0591(11) 0.0390(9) 0.0351(9) 0.0076(8) 0.0089(9) 0.0069(9) C18 0.0385(8) 0.0307(8) 0.0386(9) 0.0062(7) 0.0069(7) 0.0022(7) C19 0.0377(8) 0.0291(8) 0.0269(7) -0.0011(6) 0.0047(7) -0.0004(7) C20 0.0479(10) 0.0379(9) 0.0368(9) -0.0082(8) 0.0032(8) -0.0080(8) C21 0.0394(9) 0.0328(8) 0.0255(7) 0.0000(6) 0.0046(7) 0.0004(7) C22 0.0445(9) 0.0340(8) 0.0286(8) -0.0007(7) 0.0064(7) -0.0030(7) C23 0.0463(10) 0.0510(11) 0.0265(8) -0.0003(7) 0.0064(7) -0.0114(8) C24 0.0389(9) 0.0739(14) 0.0280(8) 0.0054(9) 0.0073(7) 0.0031(10) C25 0.0544(11) 0.0578(12) 0.0392(10) 0.0125(9) 0.0166(9) 0.0194(10) C26 0.0533(11) 0.0379(9) 0.0377(9) 0.0069(8) 0.0159(8) 0.0050(9) C27 0.0303(8) 0.0292(7) 0.0327(8) -0.0032(6) 0.0001(7) -0.0012(6) C28 0.0285(8) 0.0328(8) 0.0434(9) -0.0041(7) 0.0047(7) -0.0016(7) C29 0.0310(9) 0.0505(11) 0.0624(12) -0.0122(10) 0.0080(9) -0.0075(8) C30 0.0301(7) 0.0287(7) 0.0256(7) -0.0023(6) 0.0015(6) 0.0015(6) C31 0.0347(8) 0.0297(8) 0.0255(7) -0.0020(6) 0.0042(7) 0.0038(6) C32 0.0416(10) 0.0397(9) 0.0292(8) 0.0049(7) 0.0020(7) 0.0055(7) C33 0.0626(13) 0.0472(11) 0.0367(9) 0.0128(8) 0.0128(9) 0.0193(10) C34 0.0787(15) 0.0288(9) 0.0601(13) 0.0058(9) 0.0251(12) 0.0098(10) C35 0.0717(15) 0.0313(10) 0.0836(17) -0.0133(11) 0.0034(13) -0.0075(10) C36 0.0474(11) 0.0353(9) 0.0631(13) -0.0080(9) -0.0105(9) 0.0005(8) C37 0.0565(11) 0.0359(9) 0.0270(8) -0.0051(7) -0.0039(8) 0.0093(8) C38 0.0971(18) 0.0547(12) 0.0273(9) 0.0011(9) -0.0001(11) -0.0024(12) C39 0.0518(12) 0.0520(12) 0.0758(15) -0.0103(11) 0.0195(12) -0.0263(10) _refine_ls_extinction_method None _oxford_refine_ls_scale 5.13(9) 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 F1 . B2 . 1.360(3) yes B2 . F3 . 1.367(3) yes B2 . F4 . 1.373(3) yes B2 . F5 . 1.386(3) yes O6 . C7 . 1.324(2) yes O6 . C39 . 1.451(3) yes C7 . O8 . 1.213(2) yes C7 . C9 . 1.505(2) yes C9 . C10 . 1.550(2) yes C9 . C30 . 1.577(2) yes C9 . H91 . 1.043 no C10 . N11 . 1.5221(19) yes C10 . C27 . 1.496(2) yes C10 . H101 . 1.013 no N11 . C12 . 1.5201(19) yes N11 . C19 . 1.551(2) yes N11 . H111 . 0.780 no C12 . C13 . 1.508(2) yes C12 . H122 . 1.017 no C12 . H121 . 0.946 no C13 . C14 . 1.388(2) yes C13 . C18 . 1.391(2) yes C14 . C15 . 1.380(3) yes C14 . H141 . 0.888 no C15 . C16 . 1.389(3) yes C15 . H151 . 0.924 no C16 . C17 . 1.379(3) yes C16 . H161 . 0.983 no C17 . C18 . 1.384(3) yes C17 . H171 . 0.963 no C18 . H181 . 0.962 no C19 . C20 . 1.526(2) yes C19 . C21 . 1.515(2) yes C19 . H191 . 0.937 no C20 . H201 . 1.049 no C20 . H202 . 1.064 no C20 . H203 . 1.049 no C21 . C22 . 1.394(2) yes C21 . C26 . 1.386(3) yes C22 . C23 . 1.386(3) yes C22 . H221 . 0.949 no C23 . C24 . 1.379(3) yes C23 . H231 . 0.905 no C24 . C25 . 1.382(3) yes C24 . H241 . 0.920 no C25 . C26 . 1.389(3) yes C25 . H251 . 0.958 no C26 . H261 . 0.946 no C27 . C28 . 1.326(2) yes C27 . H271 . 0.977 no C28 . C29 . 1.496(2) yes C28 . H281 . 1.022 no C29 . H292 . 1.000 no C29 . H293 . 1.024 no C29 . H291 . 1.058 no C30 . C31 . 1.521(2) yes C30 . C37 . 1.505(2) yes C30 . H301 . 0.972 no C31 . C32 . 1.388(2) yes C31 . C36 . 1.386(3) yes C32 . C33 . 1.397(3) yes C32 . H321 . 0.949 no C33 . C34 . 1.370(3) yes C33 . H331 . 1.021 no C34 . C35 . 1.360(4) yes C34 . H341 . 0.935 no C35 . C36 . 1.396(3) yes C35 . H351 . 1.005 no C36 . H361 . 0.992 no C37 . C38 . 1.317(3) yes C37 . H371 . 1.000 no C38 . H381 . 0.938 no C38 . H382 . 1.006 no C39 . H392 . 1.040 no C39 . H393 . 1.008 no C39 . H391 . 1.037 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 F1 . B2 . F3 . 113.5(2) yes F1 . B2 . F4 . 109.72(19) yes F3 . B2 . F4 . 108.08(19) yes F1 . B2 . F5 . 108.05(19) yes F3 . B2 . F5 . 107.46(19) yes F4 . B2 . F5 . 110.0(2) yes C7 . O6 . C39 . 116.15(17) yes O6 . C7 . O8 . 123.39(16) yes O6 . C7 . C9 . 111.81(15) yes O8 . C7 . C9 . 124.79(15) yes C7 . C9 . C10 . 113.57(13) yes C7 . C9 . C30 . 109.12(13) yes C10 . C9 . C30 . 105.80(12) yes C7 . C9 . H91 . 108.8 no C10 . C9 . H91 . 112.0 no C30 . C9 . H91 . 107.3 no C9 . C10 . N11 . 113.09(12) yes C9 . C10 . C27 . 111.33(13) yes N11 . C10 . C27 . 112.40(12) yes C9 . C10 . H101 . 103.4 no N11 . C10 . H101 . 110.2 no C27 . C10 . H101 . 105.9 no C10 . N11 . C12 . 110.88(11) yes C10 . N11 . C19 . 115.18(12) yes C12 . N11 . C19 . 114.63(12) yes C10 . N11 . H111 . 109.8 no C12 . N11 . H111 . 106.1 no C19 . N11 . H111 . 99.2 no N11 . C12 . C13 . 110.58(12) yes N11 . C12 . H122 . 105.6 no C13 . C12 . H122 . 111.2 no N11 . C12 . H121 . 109.3 no C13 . C12 . H121 . 106.6 no H122 . C12 . H121 . 113.7 no C12 . C13 . C14 . 119.19(15) yes C12 . C13 . C18 . 121.79(15) yes C14 . C13 . C18 . 119.02(17) yes C13 . C14 . C15 . 121.13(17) yes C13 . C14 . H141 . 119.8 no C15 . C14 . H141 . 119.1 no C14 . C15 . C16 . 119.29(18) yes C14 . C15 . H151 . 118.7 no C16 . C15 . H151 . 121.9 no C15 . C16 . C17 . 120.14(18) yes C15 . C16 . H161 . 120.0 no C17 . C16 . H161 . 119.9 no C16 . C17 . C18 . 120.37(18) yes C16 . C17 . H171 . 120.3 no C18 . C17 . H171 . 119.3 no C13 . C18 . C17 . 120.04(17) yes C13 . C18 . H181 . 116.7 no C17 . C18 . H181 . 123.2 no N11 . C19 . C20 . 112.64(13) yes N11 . C19 . C21 . 107.11(13) yes C20 . C19 . C21 . 114.88(14) yes N11 . C19 . H191 . 106.8 no C20 . C19 . H191 . 106.8 no C21 . C19 . H191 . 108.3 no C19 . C20 . H201 . 109.2 no C19 . C20 . H202 . 99.2 no H201 . C20 . H202 . 111.1 no C19 . C20 . H203 . 107.3 no H201 . C20 . H203 . 118.1 no H202 . C20 . H203 . 110.2 no C19 . C21 . C22 . 118.90(15) yes C19 . C21 . C26 . 122.37(16) yes C22 . C21 . C26 . 118.73(17) yes C21 . C22 . C23 . 120.56(17) yes C21 . C22 . H221 . 115.2 no C23 . C22 . H221 . 124.1 no C22 . C23 . C24 . 120.12(18) yes C22 . C23 . H231 . 121.9 no C24 . C23 . H231 . 118.0 no C23 . C24 . C25 . 119.93(18) yes C23 . C24 . H241 . 119.4 no C25 . C24 . H241 . 120.7 no C24 . C25 . C26 . 120.02(19) yes C24 . C25 . H251 . 117.6 no C26 . C25 . H251 . 122.0 no C25 . C26 . C21 . 120.63(18) yes C25 . C26 . H261 . 120.8 no C21 . C26 . H261 . 118.4 no C10 . C27 . C28 . 121.53(16) yes C10 . C27 . H271 . 117.0 no C28 . C27 . H271 . 121.5 no C27 . C28 . C29 . 125.12(18) yes C27 . C28 . H281 . 120.1 no C29 . C28 . H281 . 114.7 no C28 . C29 . H292 . 102.4 no C28 . C29 . H293 . 107.6 no H292 . C29 . H293 . 107.0 no C28 . C29 . H291 . 109.4 no H292 . C29 . H291 . 111.2 no H293 . C29 . H291 . 118.0 no C9 . C30 . C31 . 112.73(12) yes C9 . C30 . C37 . 110.43(13) yes C31 . C30 . C37 . 113.73(14) yes C9 . C30 . H301 . 110.2 no C31 . C30 . H301 . 104.2 no C37 . C30 . H301 . 105.1 no C30 . C31 . C32 . 118.67(15) yes C30 . C31 . C36 . 122.91(16) yes C32 . C31 . C36 . 118.41(16) yes C31 . C32 . C33 . 120.64(19) yes C31 . C32 . H321 . 122.9 no C33 . C32 . H321 . 116.5 no C32 . C33 . C34 . 120.1(2) yes C32 . C33 . H331 . 120.4 no C34 . C33 . H331 . 119.4 no C33 . C34 . C35 . 119.68(18) yes C33 . C34 . H341 . 118.1 no C35 . C34 . H341 . 122.3 no C34 . C35 . C36 . 121.1(2) yes C34 . C35 . H351 . 124.6 no C36 . C35 . H351 . 114.3 no C35 . C36 . C31 . 120.0(2) yes C35 . C36 . H361 . 117.3 no C31 . C36 . H361 . 122.4 no C30 . C37 . C38 . 123.8(2) yes C30 . C37 . H371 . 115.2 no C38 . C37 . H371 . 121.0 no C37 . C38 . H381 . 120.1 no C37 . C38 . H382 . 121.4 no H381 . C38 . H382 . 118.1 no O6 . C39 . H392 . 112.6 no O6 . C39 . H393 . 109.7 no H392 . C39 . H393 . 114.6 no O6 . C39 . H391 . 105.4 no H392 . C39 . H391 . 107.2 no H393 . C39 . H391 . 106.8 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 C20 . H202 . C27 . 133.43(6) 1.064 2.563 3.383(3) yes C29 . H291 . O8 1_655 132.89(6) 1.058 2.543 3.354(3) yes N11 . H111 . O8 . 137.60(5) 0.780 2.115 2.742(3) yes _iucr_refine_instruction_details_constraints ; # # Punched on 15/04/13 at 17:02:14 # #LIST 12 BLOCK SCALE X'S, U'S CONT ENANTIO RIDE C ( 9,X'S) H ( 91,X'S) RIDE C ( 10,X'S) H ( 101,X'S) RIDE N ( 11,X'S) H ( 111,X'S) RIDE C ( 12,X'S) H ( 122,X'S) H ( 121,X'S) RIDE C ( 14,X'S) H ( 141,X'S) RIDE C ( 15,X'S) H ( 151,X'S) RIDE C ( 16,X'S) H ( 161,X'S) RIDE C ( 17,X'S) H ( 171,X'S) RIDE C ( 18,X'S) H ( 181,X'S) RIDE C ( 19,X'S) H ( 191,X'S) RIDE C ( 20,X'S) H ( 201,X'S) H ( 202,X'S) H ( 203,X'S) RIDE C ( 22,X'S) H ( 221,X'S) RIDE C ( 23,X'S) H ( 231,X'S) RIDE C ( 24,X'S) H ( 241,X'S) RIDE C ( 25,X'S) H ( 251,X'S) RIDE C ( 26,X'S) H ( 261,X'S) RIDE C ( 27,X'S) H ( 271,X'S) RIDE C ( 28,X'S) H ( 281,X'S) RIDE C ( 29,X'S) H ( 292,X'S) H ( 293,X'S) H ( 291,X'S) RIDE C ( 30,X'S) H ( 301,X'S) RIDE C ( 32,X'S) H ( 321,X'S) RIDE C ( 33,X'S) H ( 331,X'S) RIDE C ( 34,X'S) H ( 341,X'S) RIDE C ( 35,X'S) H ( 351,X'S) RIDE C ( 36,X'S) H ( 361,X'S) RIDE C ( 37,X'S) H ( 371,X'S) RIDE C ( 38,X'S) H ( 381,X'S) H ( 382,X'S) RIDE C ( 39,X'S) H ( 392,X'S) H ( 393,X'S) H ( 391,X'S) END ; _iucr_refine_instruction_details_restraints ; # # Punched on 15/04/13 at 17:02:14 # #LIST 16 NO REM HREST START (DO NOT REMOVE THIS LINE) REM HREST END (DO NOT REMOVE THIS LINE) END ; _database_code_depnum_ccdc_archive 'CCDC 936128' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_20 _ccdc_journal_depnumber ? #============================================================================== _cell_length_a 7.9925(2) _cell_length_b 16.7779(4) _cell_length_c 10.6442(3) _cell_angle_alpha 90 _cell_angle_beta 111.582(3) _cell_angle_gamma 90 _cell_volume 1327.29(7) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 21 1' _symmetry_space_group_name_Hall 'P 2yb' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,y+1/2,-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' 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' 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' _cell_formula_units_Z 2 # Given Formula = C31 H35 N1 O2 # Dc = 1.13 Fooo = 488.00 Mu = 5.41 M = 453.62 # Found Formula = C31 H35 N1 O2 # Dc = 1.13 FOOO = 488.00 Mu = 5.41 M = 453.62 _chemical_formula_sum 'C31 H35 N1 O2' _chemical_formula_moiety 'C31 H35 N1 O2' _chemical_compound_source . _chemical_formula_weight 453.62 _cell_measurement_reflns_used 7162 _cell_measurement_theta_min 4 _cell_measurement_theta_max 77 _cell_measurement_temperature 150 _exptl_crystal_description plate _exptl_crystal_colour colourless _exptl_crystal_size_min 0.050 _exptl_crystal_size_mid 0.200 _exptl_crystal_size_max 0.240 _exptl_crystal_density_diffrn 1.135 _exptl_crystal_density_meas . _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 488 _exptl_absorpt_coefficient_mu 0.541 # Sheldrick geometric approximatio 0.90 0.97 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'CrysAlis, (Oxford Diffraction, 2002)' _exptl_absorpt_correction_T_min 0.73 _exptl_absorpt_correction_T_max 0.97 _diffrn_measurement_device_type 'Oxford Diffraction SuperNova' _diffrn_measurement_device Area _diffrn_radiation_monochromator graphite _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 'SuperNova, (Oxford Diffraction, 2010)' _computing_cell_refinement 'CrysAlis, (Oxford Diffraction, 2002)' _computing_data_reduction 'CrysAlis, (Oxford Diffraction, 2002)' _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 13581 _reflns_number_total 4653 _diffrn_reflns_av_R_equivalents 0.022 # Number of reflections without Friedels Law is 4653 # Number of reflections with Friedels Law is 2861 # Theoretical number of reflections is about 2807 _diffrn_reflns_theta_min 4.467 _diffrn_reflns_theta_max 77.015 _diffrn_measured_fraction_theta_max 0.985 _diffrn_reflns_theta_full 74.704 _diffrn_measured_fraction_theta_full 0.995 _diffrn_reflns_limit_h_min -9 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 20 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _reflns_limit_h_min -10 _reflns_limit_h_max 9 _reflns_limit_k_min -15 _reflns_limit_k_max 20 _reflns_limit_l_min 0 _reflns_limit_l_max 13 _oxford_diffrn_Wilson_B_factor 3.05 _oxford_diffrn_Wilson_scale 0.01 _atom_sites_solution_primary Direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_diff_density_min -0.16 _refine_diff_density_max 0.14 # 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 4635 _refine_ls_number_restraints 1 _refine_ls_number_parameters 308 _oxford_refine_ls_R_factor_ref 0.0343 _refine_ls_wR_factor_ref 0.0833 _refine_ls_goodness_of_fit_ref 0.9942 _refine_ls_shift/su_max 0.0003694 _refine_ls_shift/su_mean 0.0000394 # The values computed from all data _oxford_reflns_number_all 4635 _refine_ls_R_factor_all 0.0343 _refine_ls_wR_factor_all 0.0833 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 4412 _refine_ls_R_factor_gt 0.0325 _refine_ls_wR_factor_gt 0.0816 _refine_ls_abs_structure_Flack 0.2(2) _refine_ls_abs_structure_details 'Flack (1983), 1792 Friedel-pairs' # 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 ad _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_hydrogen_treatment constr # none, 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^) + ( 0.05P)^2^ + 0.19P] ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 ; # 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 O1 O 1.08511(14) 0.54264(8) 0.79391(10) 0.0369 1.0000 Uani . . . . . . C2 C 1.06543(19) 0.55960(10) 0.91064(14) 0.0319 1.0000 Uani . . . . . . O3 O 1.02078(19) 0.51099(9) 0.97492(13) 0.0499 1.0000 Uani . . . . . . C4 C 1.10901(17) 0.64577(9) 0.95244(12) 0.0262 1.0000 Uani . . . . . . C5 C 1.26884(18) 0.64594(10) 1.09059(12) 0.0273 1.0000 Uani . . . . . . C6 C 1.32091(17) 0.72821(10) 1.15226(13) 0.0290 1.0000 Uani . . . . . . C7 C 1.3533(2) 0.74023(11) 1.28895(15) 0.0357 1.0000 Uani . . . . . . C8 C 1.4121(2) 0.81351(12) 1.34938(17) 0.0458 1.0000 Uani . . . . . . C9 C 1.4400(3) 0.87567(12) 1.2754(2) 0.0536 1.0000 Uani . . . . . . C10 C 1.4069(3) 0.86497(13) 1.1396(2) 0.0562 1.0000 Uani . . . . . . C11 C 1.3478(2) 0.79171(11) 1.07823(16) 0.0417 1.0000 Uani . . . . . . C12 C 1.4292(2) 0.60710(11) 1.07292(14) 0.0358 1.0000 Uani . . . . . . C13 C 1.4744(3) 0.53163(13) 1.09629(17) 0.0511 1.0000 Uani . . . . . . C14 C 0.94036(17) 0.69073(10) 0.95452(12) 0.0281 1.0000 Uani . . . . . . N15 N 0.79632(15) 0.68301(9) 0.81813(11) 0.0295 1.0000 Uani . . . . . . C16 C 0.7275(2) 0.75975(11) 0.75191(15) 0.0373 1.0000 Uani . . . . . . C17 C 0.8778(2) 0.80467(11) 0.72816(15) 0.0378 1.0000 Uani . . . . . . C18 C 0.9443(2) 0.87665(12) 0.7914(2) 0.0503 1.0000 Uani . . . . . . C19 C 1.0773(3) 0.91662(13) 0.7661(3) 0.0627 1.0000 Uani . . . . . . C20 C 1.1483(3) 0.88627(15) 0.6773(3) 0.0736 1.0000 Uani . . . . . . C21 C 1.0893(4) 0.81257(19) 0.6152(3) 0.0827 1.0000 Uani . . . . . . C22 C 0.9534(3) 0.77245(15) 0.64052(19) 0.0609 1.0000 Uani . . . . . . C23 C 0.6251(3) 0.80942(15) 0.8215(2) 0.0614 1.0000 Uani . . . . . . C24 C 0.6528(2) 0.62718(12) 0.80941(14) 0.0378 1.0000 Uani . . . . . . C25 C 0.5487(2) 0.59824(10) 0.66705(14) 0.0324 1.0000 Uani . . . . . . C26 C 0.3640(2) 0.58671(11) 0.62444(16) 0.0413 1.0000 Uani . . . . . . C27 C 0.2702(2) 0.55170(13) 0.49955(18) 0.0505 1.0000 Uani . . . . . . C28 C 0.3589(3) 0.52994(12) 0.41613(16) 0.0491 1.0000 Uani . . . . . . C29 C 0.5416(2) 0.54371(11) 0.45572(16) 0.0441 1.0000 Uani . . . . . . C30 C 0.6364(2) 0.57742(11) 0.58056(15) 0.0367 1.0000 Uani . . . . . . C31 C 0.88940(18) 0.66712(11) 1.07236(13) 0.0340 1.0000 Uani . . . . . . C32 C 0.8858(2) 0.71788(14) 1.16699(16) 0.0459 1.0000 Uani . . . . . . C33 C 0.8447(2) 0.69512(18) 1.28898(17) 0.0686 1.0000 Uani . . . . . . C34 C 1.0570(3) 0.45983(12) 0.7528(2) 0.0528 1.0000 Uani . . . . . . H41 H 1.1531 0.6724 0.8860 0.0309 1.0000 Uiso R . . . . . H51 H 1.2248 0.6119 1.1516 0.0326 1.0000 Uiso R . . . . . H71 H 1.3355 0.6934 1.3419 0.0478 1.0000 Uiso R . . . . . H81 H 1.4367 0.8209 1.4469 0.0585 1.0000 Uiso R . . . . . H91 H 1.4806 0.9290 1.3205 0.0661 1.0000 Uiso R . . . . . H101 H 1.4275 0.9078 1.0839 0.0672 1.0000 Uiso R . . . . . H111 H 1.3239 0.7855 0.9826 0.0553 1.0000 Uiso R . . . . . H121 H 1.5013 0.6408 1.0382 0.0489 1.0000 Uiso R . . . . . H131 H 1.5798 0.5088 1.0824 0.0645 1.0000 Uiso R . . . . . H132 H 1.3984 0.4956 1.1245 0.0658 1.0000 Uiso R . . . . . H141 H 0.9776 0.7494 0.9698 0.0364 1.0000 Uiso R . . . . . H161 H 0.6357 0.7426 0.6582 0.0476 1.0000 Uiso R . . . . . H181 H 0.8945 0.8982 0.8583 0.0628 1.0000 Uiso R . . . . . H191 H 1.1215 0.9678 0.8106 0.0813 1.0000 Uiso R . . . . . H201 H 1.2422 0.9145 0.6584 0.0881 1.0000 Uiso R . . . . . H211 H 1.1399 0.7909 0.5527 0.1037 1.0000 Uiso R . . . . . H221 H 0.9071 0.7216 0.5982 0.0763 1.0000 Uiso R . . . . . H231 H 0.5725 0.8577 0.7684 0.0952 1.0000 Uiso R . . . . . H233 H 0.7097 0.8262 0.9120 0.0954 1.0000 Uiso R . . . . . H232 H 0.5278 0.7752 0.8328 0.0954 1.0000 Uiso R . . . . . H242 H 0.5664 0.6500 0.8487 0.0518 1.0000 Uiso R . . . . . H241 H 0.7086 0.5786 0.8665 0.0516 1.0000 Uiso R . . . . . H261 H 0.3036 0.6037 0.6846 0.0525 1.0000 Uiso R . . . . . H271 H 0.1436 0.5410 0.4730 0.0642 1.0000 Uiso R . . . . . H281 H 0.2891 0.5043 0.3274 0.0596 1.0000 Uiso R . . . . . H291 H 0.6071 0.5299 0.3941 0.0538 1.0000 Uiso R . . . . . H301 H 0.7651 0.5873 0.6095 0.0441 1.0000 Uiso R . . . . . H311 H 0.8592 0.6108 1.0760 0.0466 1.0000 Uiso R . . . . . H321 H 0.9171 0.7734 1.1555 0.0631 1.0000 Uiso R . . . . . H331 H 0.7488 0.7314 1.2947 0.1023 1.0000 Uiso R . . . . . H333 H 0.9561 0.7041 1.3730 0.1019 1.0000 Uiso R . . . . . H332 H 0.8032 0.6380 1.2822 0.1027 1.0000 Uiso R . . . . . H342 H 1.0645 0.4569 0.6610 0.0847 1.0000 Uiso R . . . . . H341 H 1.1567 0.4286 0.8203 0.0844 1.0000 Uiso R . . . . . H343 H 0.9360 0.4430 0.7520 0.0848 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 O1 0.0440(5) 0.0351(6) 0.0352(5) -0.0085(5) 0.0187(4) -0.0018(5) C2 0.0326(6) 0.0328(8) 0.0325(6) -0.0032(6) 0.0147(5) -0.0022(6) O3 0.0738(8) 0.0341(7) 0.0541(7) -0.0046(5) 0.0378(6) -0.0158(6) C4 0.0293(6) 0.0270(7) 0.0247(6) 0.0000(5) 0.0127(5) -0.0030(5) C5 0.0305(6) 0.0279(8) 0.0254(6) 0.0025(5) 0.0123(5) 0.0012(6) C6 0.0251(6) 0.0304(8) 0.0304(6) 0.0018(6) 0.0088(5) 0.0004(5) C7 0.0401(7) 0.0342(9) 0.0313(7) -0.0001(6) 0.0114(6) 0.0032(7) C8 0.0504(9) 0.0398(10) 0.0401(8) -0.0085(7) 0.0083(7) 0.0036(8) C9 0.0553(10) 0.0331(10) 0.0581(11) -0.0064(9) 0.0040(8) -0.0047(8) C10 0.0669(12) 0.0349(10) 0.0571(11) 0.0072(9) 0.0112(9) -0.0135(9) C11 0.0473(9) 0.0388(10) 0.0364(7) 0.0055(7) 0.0124(7) -0.0084(8) C12 0.0345(7) 0.0428(9) 0.0298(6) -0.0038(6) 0.0115(5) 0.0057(7) C13 0.0485(9) 0.0503(11) 0.0455(9) -0.0102(8) 0.0068(7) 0.0162(8) C14 0.0285(6) 0.0307(8) 0.0254(6) -0.0032(6) 0.0103(5) -0.0018(6) N15 0.0296(5) 0.0322(7) 0.0260(5) -0.0009(5) 0.0093(4) -0.0043(5) C16 0.0331(7) 0.0376(9) 0.0356(7) 0.0005(6) 0.0062(6) 0.0028(6) C17 0.0411(8) 0.0305(8) 0.0324(7) 0.0044(6) 0.0022(6) -0.0020(7) C18 0.0434(8) 0.0303(9) 0.0584(10) -0.0006(8) -0.0035(7) 0.0027(7) C19 0.0465(10) 0.0348(10) 0.0823(15) 0.0067(10) -0.0051(10) -0.0058(8) C20 0.0550(11) 0.0667(16) 0.0795(15) 0.0303(13) 0.0015(11) -0.0304(11) C21 0.0937(17) 0.100(2) 0.0669(13) -0.0102(14) 0.0438(13) -0.0525(16) C22 0.0799(14) 0.0646(13) 0.0466(10) -0.0165(9) 0.0334(9) -0.0394(11) C23 0.0515(10) 0.0577(13) 0.0757(13) -0.0023(11) 0.0242(10) 0.0176(10) C24 0.0358(7) 0.0505(10) 0.0294(7) -0.0025(6) 0.0146(6) -0.0111(7) C25 0.0335(7) 0.0311(8) 0.0306(6) 0.0026(6) 0.0096(5) -0.0055(6) C26 0.0353(7) 0.0448(10) 0.0423(8) 0.0054(7) 0.0125(6) -0.0072(7) C27 0.0398(8) 0.0528(12) 0.0456(8) 0.0084(8) 0.0001(7) -0.0168(8) C28 0.0639(11) 0.0369(10) 0.0317(7) 0.0020(7) 0.0000(7) -0.0132(8) C29 0.0597(10) 0.0345(9) 0.0341(7) -0.0016(7) 0.0125(7) 0.0010(8) C30 0.0380(7) 0.0377(9) 0.0322(7) 0.0015(6) 0.0105(6) -0.0006(6) C31 0.0278(6) 0.0491(10) 0.0263(6) -0.0043(6) 0.0112(5) -0.0035(6) C32 0.0353(7) 0.0699(13) 0.0348(7) -0.0150(8) 0.0156(6) -0.0017(8) C33 0.0437(9) 0.134(2) 0.0328(8) -0.0219(11) 0.0200(7) -0.0038(12) C34 0.0657(11) 0.0407(10) 0.0545(10) -0.0178(8) 0.0249(9) -0.0039(9) _refine_ls_extinction_method None _oxford_refine_ls_scale 8.7(2) 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 O1 . C2 . 1.3391(16) yes O1 . C34 . 1.449(2) yes C2 . O3 . 1.2002(18) yes C2 . C4 . 1.515(2) yes C4 . C5 . 1.5531(18) yes C4 . C14 . 1.5520(18) yes C4 . H41 . 1.003 no C5 . C6 . 1.519(2) yes C5 . C12 . 1.5097(19) yes C5 . H51 . 1.020 no C6 . C7 . 1.3955(19) yes C6 . C11 . 1.388(2) yes C7 . C8 . 1.387(2) yes C7 . H71 . 1.007 no C8 . C9 . 1.373(3) yes C8 . H81 . 0.990 no C9 . C10 . 1.382(3) yes C9 . H91 . 1.011 no C10 . C11 . 1.391(3) yes C10 . H101 . 0.983 no C11 . H111 . 0.970 no C12 . C13 . 1.315(3) yes C12 . H121 . 0.972 no C13 . H131 . 0.984 no C13 . H132 . 0.979 no C14 . N15 . 1.4900(16) yes C14 . C31 . 1.5073(18) yes C14 . H141 . 1.024 no N15 . C16 . 1.474(2) yes N15 . C24 . 1.4570(19) yes C16 . C17 . 1.516(2) yes C16 . C23 . 1.536(3) yes C16 . H161 . 1.038 no C17 . C18 . 1.390(2) yes C17 . C22 . 1.394(3) yes C18 . C19 . 1.365(3) yes C18 . H181 . 1.002 no C19 . C20 . 1.367(4) yes C19 . H191 . 0.982 no C20 . C21 . 1.400(4) yes C20 . H201 . 0.969 no C21 . C22 . 1.387(3) yes C21 . H211 . 0.967 no C22 . H221 . 0.972 no C23 . H231 . 0.988 no C23 . H233 . 0.993 no C23 . H232 . 1.010 no C24 . C25 . 1.5155(19) yes C24 . H242 . 1.005 no C24 . H241 . 1.017 no C25 . C26 . 1.389(2) yes C25 . C30 . 1.391(2) yes C26 . C27 . 1.393(2) yes C26 . H261 . 0.976 no C27 . C28 . 1.374(3) yes C27 . H271 . 0.962 no C28 . C29 . 1.382(3) yes C28 . H281 . 1.001 no C29 . C30 . 1.385(2) yes C29 . H291 . 1.006 no C30 . H301 . 0.973 no C31 . C32 . 1.327(2) yes C31 . H311 . 0.980 no C32 . C33 . 1.501(2) yes C32 . H321 . 0.984 no C33 . H331 . 0.998 no C33 . H333 . 1.015 no C33 . H332 . 1.008 no C34 . H342 . 1.002 no C34 . H341 . 1.003 no C34 . H343 . 1.005 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 C2 . O1 . C34 . 115.20(13) yes O1 . C2 . O3 . 123.07(15) yes O1 . C2 . C4 . 112.49(12) yes O3 . C2 . C4 . 124.43(13) yes C2 . C4 . C5 . 107.46(11) yes C2 . C4 . C14 . 111.16(11) yes C5 . C4 . C14 . 113.69(10) yes C2 . C4 . H41 . 108.7 no C5 . C4 . H41 . 106.7 no C14 . C4 . H41 . 109.0 no C4 . C5 . C6 . 114.20(11) yes C4 . C5 . C12 . 108.75(10) yes C6 . C5 . C12 . 109.62(12) yes C4 . C5 . H51 . 104.2 no C6 . C5 . H51 . 109.7 no C12 . C5 . H51 . 110.2 no C5 . C6 . C7 . 119.87(13) yes C5 . C6 . C11 . 121.80(12) yes C7 . C6 . C11 . 118.22(14) yes C6 . C7 . C8 . 120.86(15) yes C6 . C7 . H71 . 117.4 no C8 . C7 . H71 . 121.7 no C7 . C8 . C9 . 120.40(16) yes C7 . C8 . H81 . 120.0 no C9 . C8 . H81 . 119.6 no C8 . C9 . C10 . 119.46(17) yes C8 . C9 . H91 . 119.4 no C10 . C9 . H91 . 121.1 no C9 . C10 . C11 . 120.50(18) yes C9 . C10 . H101 . 121.7 no C11 . C10 . H101 . 117.7 no C10 . C11 . C6 . 120.55(16) yes C10 . C11 . H111 . 119.4 no C6 . C11 . H111 . 120.1 no C5 . C12 . C13 . 125.37(16) yes C5 . C12 . H121 . 116.4 no C13 . C12 . H121 . 118.1 no C12 . C13 . H131 . 122.5 no C12 . C13 . H132 . 119.6 no H131 . C13 . H132 . 117.9 no C4 . C14 . N15 . 107.92(10) yes C4 . C14 . C31 . 112.71(11) yes N15 . C14 . C31 . 116.07(11) yes C4 . C14 . H141 . 105.5 no N15 . C14 . H141 . 108.3 no C31 . C14 . H141 . 105.8 no C14 . N15 . C16 . 114.12(12) yes C14 . N15 . C24 . 115.21(11) yes C16 . N15 . C24 . 112.63(12) yes N15 . C16 . C17 . 109.59(12) yes N15 . C16 . C23 . 114.50(15) yes C17 . C16 . C23 . 113.96(16) yes N15 . C16 . H161 . 103.0 no C17 . C16 . H161 . 107.5 no C23 . C16 . H161 . 107.4 no C16 . C17 . C18 . 122.46(17) yes C16 . C17 . C22 . 118.94(15) yes C18 . C17 . C22 . 118.59(17) yes C17 . C18 . C19 . 121.2(2) yes C17 . C18 . H181 . 118.5 no C19 . C18 . H181 . 120.3 no C18 . C19 . C20 . 120.3(2) yes C18 . C19 . H191 . 120.1 no C20 . C19 . H191 . 119.5 no C19 . C20 . C21 . 120.1(2) yes C19 . C20 . H201 . 120.8 no C21 . C20 . H201 . 119.1 no C20 . C21 . C22 . 119.3(3) yes C20 . C21 . H211 . 120.2 no C22 . C21 . H211 . 120.5 no C17 . C22 . C21 . 120.4(2) yes C17 . C22 . H221 . 117.8 no C21 . C22 . H221 . 121.9 no C16 . C23 . H231 . 111.1 no C16 . C23 . H233 . 109.2 no H231 . C23 . H233 . 108.5 no C16 . C23 . H232 . 108.7 no H231 . C23 . H232 . 110.5 no H233 . C23 . H232 . 108.9 no N15 . C24 . C25 . 113.55(11) yes N15 . C24 . H242 . 111.9 no C25 . C24 . H242 . 109.2 no N15 . C24 . H241 . 108.4 no C25 . C24 . H241 . 107.5 no H242 . C24 . H241 . 105.9 no C24 . C25 . C26 . 119.86(14) yes C24 . C25 . C30 . 121.14(13) yes C26 . C25 . C30 . 118.84(14) yes C25 . C26 . C27 . 120.30(16) yes C25 . C26 . H261 . 117.9 no C27 . C26 . H261 . 121.8 no C26 . C27 . C28 . 120.27(16) yes C26 . C27 . H271 . 119.8 no C28 . C27 . H271 . 119.8 no C27 . C28 . C29 . 119.81(15) yes C27 . C28 . H281 . 118.9 no C29 . C28 . H281 . 121.3 no C28 . C29 . C30 . 120.27(17) yes C28 . C29 . H291 . 120.5 no C30 . C29 . H291 . 119.2 no C25 . C30 . C29 . 120.44(15) yes C25 . C30 . H301 . 118.6 no C29 . C30 . H301 . 121.0 no C14 . C31 . C32 . 123.42(16) yes C14 . C31 . H311 . 115.6 no C32 . C31 . H311 . 120.9 no C31 . C32 . C33 . 124.5(2) yes C31 . C32 . H321 . 115.8 no C33 . C32 . H321 . 119.6 no C32 . C33 . H331 . 108.3 no C32 . C33 . H333 . 108.9 no H331 . C33 . H333 . 107.5 no C32 . C33 . H332 . 110.6 no H331 . C33 . H332 . 110.2 no H333 . C33 . H332 . 111.3 no O1 . C34 . H342 . 106.5 no O1 . C34 . H341 . 106.9 no H342 . C34 . H341 . 110.9 no O1 . C34 . H343 . 108.3 no H342 . C34 . H343 . 112.4 no H341 . C34 . H343 . 111.6 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 C18 . H181 . O3 2_757 134.41(6) 1.002 2.511 3.291(3) yes C24 . H241 . O3 . 139.03(4) 1.017 2.594 3.427(3) yes _iucr_refine_instruction_details_constraints ; # # Punched on 02/04/13 at 16:08:51 # #LIST 12 BLOCK SCALE X'S, U'S CONT ENANTIO RIDE C ( 4,X'S) H ( 41,X'S) RIDE C ( 5,X'S) H ( 51,X'S) RIDE C ( 7,X'S) H ( 71,X'S) RIDE C ( 8,X'S) H ( 81,X'S) RIDE C ( 9,X'S) H ( 91,X'S) RIDE C ( 10,X'S) H ( 101,X'S) RIDE C ( 11,X'S) H ( 111,X'S) RIDE C ( 12,X'S) H ( 121,X'S) RIDE C ( 13,X'S) H ( 131,X'S) H ( 132,X'S) RIDE C ( 14,X'S) H ( 141,X'S) RIDE C ( 16,X'S) H ( 161,X'S) RIDE C ( 18,X'S) H ( 181,X'S) RIDE C ( 19,X'S) H ( 191,X'S) RIDE C ( 20,X'S) H ( 201,X'S) RIDE C ( 21,X'S) H ( 211,X'S) RIDE C ( 22,X'S) H ( 221,X'S) RIDE C ( 23,X'S) H ( 231,X'S) H ( 233,X'S) H ( 232,X'S) RIDE C ( 24,X'S) H ( 242,X'S) H ( 241,X'S) RIDE C ( 26,X'S) H ( 261,X'S) RIDE C ( 27,X'S) H ( 271,X'S) RIDE C ( 28,X'S) H ( 281,X'S) RIDE C ( 29,X'S) H ( 291,X'S) RIDE C ( 30,X'S) H ( 301,X'S) RIDE C ( 31,X'S) H ( 311,X'S) RIDE C ( 32,X'S) H ( 321,X'S) RIDE C ( 33,X'S) H ( 331,X'S) H ( 333,X'S) H ( 332,X'S) RIDE C ( 34,X'S) H ( 342,X'S) H ( 341,X'S) H ( 343,X'S) END ; _iucr_refine_instruction_details_restraints ; # # Punched on 02/04/13 at 16:08:51 # #LIST 16 NO REM HREST START (DO NOT REMOVE THIS LINE) REM HREST END (DO NOT REMOVE THIS LINE) END ; _database_code_depnum_ccdc_archive 'CCDC 936129' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_29.C7H4F2O2.CHCl3 _ccdc_journal_depnumber ? #============================================================================== _cell_length_a 25.0016(5) _cell_length_b 6.69150(10) _cell_length_c 12.9605(2) _cell_angle_alpha 90 _cell_angle_beta 110.830(2) _cell_angle_gamma 90 _cell_volume 2026.55(7) _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'C 2' _symmetry_space_group_name_Hall 'C 2y' loop_ _symmetry_equiv_pos_as_xyz x,y,z x+1/2,y+1/2,z -x,y,-z -x+1/2,y+1/2,-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' 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' F 0.0727 0.0534 3.5392 10.2825 2.6412 4.2944 1.5170 0.2615 1.0243 26.1476 0.2776 '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' 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' _cell_formula_units_Z 4 # Given Formula = C16 H20 Cl3 F2 N1 O4 # Dc = 1.42 Fooo = 896.00 Mu = 44.52 M = 434.69 # Found Formula = C16 H20 Cl3 F2 N1 O4 # Dc = 1.42 FOOO = 896.00 Mu = 44.52 M = 434.69 _chemical_formula_sum 'C16 H20 Cl3 F2 N1 O4' _chemical_formula_moiety 'C16 H20 Cl3 F2 N1 O4' _chemical_compound_source . _chemical_formula_weight 434.69 _cell_measurement_reflns_used 13241 _cell_measurement_theta_min 4 _cell_measurement_theta_max 76 _cell_measurement_temperature 150 _exptl_crystal_description prism _exptl_crystal_colour colourless _exptl_crystal_size_min 0.110 _exptl_crystal_size_mid 0.120 _exptl_crystal_size_max 0.290 _exptl_crystal_density_diffrn 1.425 _exptl_crystal_density_meas . _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 896.000 _exptl_absorpt_coefficient_mu 4.452 # Sheldrick geometric approximatio 0.59 0.61 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'CrysAlis, (Oxford Diffraction, 2002)' _exptl_absorpt_correction_T_min 0.27 _exptl_absorpt_correction_T_max 0.61 _diffrn_measurement_device_type 'Oxford Diffraction SuperNova' _diffrn_measurement_device Area _diffrn_radiation_monochromator graphite _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 'SuperNova, (Oxford Diffraction, 2010)' _computing_cell_refinement 'CrysAlis, (Oxford Diffraction, 2002)' _computing_data_reduction 'CrysAlis, (Oxford Diffraction, 2002)' _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 19694 _reflns_number_total 4226 _diffrn_reflns_av_R_equivalents 0.023 # Number of reflections without Friedels Law is 4226 # Number of reflections with Friedels Law is 2316 # Theoretical number of reflections is about 2119 _diffrn_reflns_theta_min 3.649 _diffrn_reflns_theta_max 76.104 _diffrn_measured_fraction_theta_max 0.997 _diffrn_reflns_theta_full 76.104 _diffrn_measured_fraction_theta_full 0.997 _diffrn_reflns_limit_h_min -31 _diffrn_reflns_limit_h_max 31 _diffrn_reflns_limit_k_min -8 _diffrn_reflns_limit_k_max 8 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _reflns_limit_h_min -31 _reflns_limit_h_max 29 _reflns_limit_k_min -8 _reflns_limit_k_max 8 _reflns_limit_l_min 0 _reflns_limit_l_max 16 _oxford_diffrn_Wilson_B_factor 3.94 _oxford_diffrn_Wilson_scale 0.11 _atom_sites_solution_primary Other #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_diff_density_min -0.44 _refine_diff_density_max 0.25 # 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 4207 _refine_ls_number_restraints 1 _refine_ls_number_parameters 255 _oxford_refine_ls_R_factor_ref 0.0326 _refine_ls_wR_factor_ref 0.0822 _refine_ls_goodness_of_fit_ref 0.9080 _refine_ls_shift/su_max 0.0046285 _refine_ls_shift/su_mean 0.0002582 # The values computed from all data _oxford_reflns_number_all 4207 _refine_ls_R_factor_all 0.0326 _refine_ls_wR_factor_all 0.0822 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 4120 _refine_ls_R_factor_gt 0.0321 _refine_ls_wR_factor_gt 0.0817 _refine_ls_abs_structure_Flack 0.005(11) _refine_ls_abs_structure_details 'Flack (1983), 1910 Friedel-pairs' # 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 ad _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_hydrogen_treatment mixed # none, 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^) + ( 0.05P)^2^ + 1.14P] ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 ; # 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 Cl1 Cl 0.47541(2) 0.76266(10) 0.69804(5) 0.0615 1.0000 Uani . . . . . . C2 C 0.46594(8) 1.0114(4) 0.7312(2) 0.0577 1.0000 Uani . . . . . . F7 F 0.38326(5) 0.40957(16) 0.73296(9) 0.0453 1.0000 Uani . . . . . . C8 C 0.38173(7) 0.5151(3) 0.82074(14) 0.0378 1.0000 Uani . . . . . . C9 C 0.35460(6) 0.6988(2) 0.80173(13) 0.0319 1.0000 Uani . . . . . . C10 C 0.32656(6) 0.7860(2) 0.68779(13) 0.0309 1.0000 Uani . . . . . . O11 O 0.33698(5) 0.96428(18) 0.67469(12) 0.0424 1.0000 Uani . . . . . . O12 O 0.29426(5) 0.67336(18) 0.61444(9) 0.0370 1.0000 Uani . . . . . . C13 C 0.35563(8) 0.8002(3) 0.89641(16) 0.0490 1.0000 Uani . . . . . . F14 F 0.32959(6) 0.9794(2) 0.88488(13) 0.0685 1.0000 Uani . . . . . . C15 C 0.38075(11) 0.7260(5) 1.00141(18) 0.0699 1.0000 Uani . . . . . . C16 C 0.40757(12) 0.5433(5) 1.01484(18) 0.0772 1.0000 Uani . . . . . . C17 C 0.40855(10) 0.4349(4) 0.92504(19) 0.0602 1.0000 Uani . . . . . . O18 O 0.20569(6) 0.81505(19) 0.79370(9) 0.0426 1.0000 Uani . . . . . . C19 C 0.20122(7) 1.0133(3) 0.78242(13) 0.0334 1.0000 Uani . . . . . . O20 O 0.20122(6) 1.1268(2) 0.85492(10) 0.0491 1.0000 Uani . . . . . . C21 C 0.19377(6) 1.0759(2) 0.66646(11) 0.0264 1.0000 Uani . . . . . . C22 C 0.12906(6) 1.1075(2) 0.59805(13) 0.0359 1.0000 Uani . . . . . . C23 C 0.11894(7) 1.3254(3) 0.61946(16) 0.0418 1.0000 Uani . . . . . . C24 C 0.17157(8) 1.4305(2) 0.61186(17) 0.0434 1.0000 Uani . . . . . . C25 C 0.22096(6) 1.2845(2) 0.66607(12) 0.0303 1.0000 Uani . . . . . . N26 N 0.26117(5) 1.28038(19) 0.60443(10) 0.0288 1.0000 Uani . . . . . . C27 C 0.08851(8) 0.9614(3) 0.6230(2) 0.0548 1.0000 Uani . . . . . . C28 C 0.20939(12) 0.7358(4) 0.90024(18) 0.0651 1.0000 Uani . . . . . . Cl30 Cl 0.49341(6) 0.9998(3) 0.89073(13) 0.0759 0.453(2) Uani . . P 1 1 . Cl31 Cl 0.51814(6) 1.1048(3) 0.84352(12) 0.0940 0.547(2) Uani . . P 1 2 . Cl50 Cl 0.46659(8) 1.1718(2) 0.61012(12) 0.0772 0.547(2) Uani . . P 1 2 . Cl51 Cl 0.50036(11) 1.1718(3) 0.6907(3) 0.1008 0.453(2) Uani . . P 1 1 . H151 H 0.3795 0.7998 1.0643 0.0789 1.0000 Uiso R . . . . . H161 H 0.4253 0.4932 1.0898 0.0925 1.0000 Uiso R . . . . . H171 H 0.4289 0.3077 0.9333 0.0729 1.0000 Uiso R . . . . . H211 H 0.2113 0.9744 0.6324 0.0306 1.0000 Uiso R . . . . . H221 H 0.1253 1.0969 0.5183 0.0433 1.0000 Uiso R . . . . . H232 H 0.1163 1.3325 0.6955 0.0522 1.0000 Uiso R . . . . . H231 H 0.0829 1.3748 0.5648 0.0514 1.0000 Uiso R . . . . . H242 H 0.1790 1.5604 0.6475 0.0520 1.0000 Uiso R . . . . . H241 H 0.1667 1.4447 0.5321 0.0519 1.0000 Uiso R . . . . . H251 H 0.2429 1.3209 0.7439 0.0363 1.0000 Uiso R . . . . . H271 H 0.0475 0.9941 0.5792 0.0829 1.0000 Uiso R . . . . . H272 H 0.0926 0.9750 0.7028 0.0835 1.0000 Uiso R . . . . . H273 H 0.0966 0.8242 0.6104 0.0827 1.0000 Uiso R . . . . . H283 H 0.2065 0.5908 0.8907 0.0989 1.0000 Uiso R . . . . . H282 H 0.2467 0.7728 0.9540 0.0996 1.0000 Uiso R . . . . . H281 H 0.1769 0.7878 0.9210 0.0990 1.0000 Uiso R . . . . . H262 H 0.2878 1.1837 0.6308 0.0435 1.0000 Uiso R . . . . . H261 H 0.2795 1.4023 0.6106 0.0434 1.0000 Uiso R . . . . . H263 H 0.2405 1.2556 0.5325 0.0443 1.0000 Uiso R . . . . . H21 H 0.4261 1.0432 0.7043 0.0691 0.453(2) Uiso . . P 1 1 . H22 H 0.4299 1.0246 0.7408 0.0691 0.547(2) Uiso . . P 1 2 . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 Cl1 0.0593(3) 0.0578(3) 0.0703(3) -0.0109(2) 0.0266(2) 0.0003(2) C2 0.0346(9) 0.0626(13) 0.0723(13) -0.0217(11) 0.0146(9) -0.0086(9) F7 0.0486(6) 0.0299(5) 0.0474(5) -0.0024(4) 0.0048(4) 0.0089(4) C8 0.0363(8) 0.0352(8) 0.0354(8) 0.0027(7) 0.0049(6) -0.0042(6) C9 0.0258(6) 0.0314(7) 0.0373(7) -0.0037(6) 0.0097(6) -0.0065(6) C10 0.0237(6) 0.0221(6) 0.0457(8) 0.0024(6) 0.0110(6) 0.0001(5) O11 0.0320(5) 0.0213(5) 0.0688(8) 0.0067(5) 0.0117(5) -0.0006(4) O12 0.0380(6) 0.0291(5) 0.0359(5) 0.0047(4) 0.0033(4) -0.0056(5) C13 0.0387(8) 0.0600(12) 0.0523(10) -0.0190(9) 0.0212(8) -0.0155(9) F14 0.0604(7) 0.0631(8) 0.0903(9) -0.0387(7) 0.0371(7) -0.0066(6) C15 0.0637(13) 0.108(2) 0.0409(10) -0.0206(12) 0.0219(9) -0.0260(14) C16 0.0725(15) 0.114(2) 0.0351(10) 0.0131(12) 0.0076(10) -0.0201(16) C17 0.0538(11) 0.0637(14) 0.0503(11) 0.0220(10) 0.0030(9) -0.0001(10) O18 0.0541(7) 0.0377(6) 0.0327(5) 0.0087(5) 0.0116(5) 0.0004(5) C19 0.0340(7) 0.0354(8) 0.0291(7) -0.0013(6) 0.0092(6) -0.0007(6) O20 0.0637(8) 0.0541(8) 0.0316(6) -0.0059(5) 0.0194(5) 0.0040(6) C21 0.0281(6) 0.0236(6) 0.0269(6) -0.0028(5) 0.0087(5) -0.0008(5) C22 0.0313(7) 0.0339(8) 0.0370(8) -0.0004(6) 0.0053(6) -0.0012(6) C23 0.0346(8) 0.0377(8) 0.0518(10) -0.0002(7) 0.0139(7) 0.0081(7) C24 0.0436(9) 0.0251(7) 0.0641(11) -0.0012(7) 0.0222(8) 0.0064(7) C25 0.0333(7) 0.0237(7) 0.0344(7) -0.0057(6) 0.0125(6) -0.0024(6) N26 0.0281(5) 0.0229(6) 0.0320(6) 0.0015(5) 0.0065(5) -0.0025(5) C27 0.0297(8) 0.0481(10) 0.0791(14) 0.0067(10) 0.0104(9) -0.0061(7) C28 0.0857(16) 0.0656(14) 0.0440(10) 0.0242(10) 0.0231(10) 0.0028(12) Cl30 0.0565(8) 0.0895(11) 0.0639(8) -0.0250(8) -0.0005(6) 0.0110(7) Cl31 0.0687(8) 0.1193(13) 0.0623(7) -0.0363(8) -0.0155(6) 0.0068(8) Cl50 0.1073(11) 0.0677(7) 0.0647(8) -0.0020(5) 0.0403(8) -0.0353(7) Cl51 0.1091(16) 0.0665(9) 0.166(3) -0.0054(12) 0.0964(19) -0.0293(10) _refine_ls_extinction_method None _oxford_refine_ls_scale 3.38(3) 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 . C2 . 1.756(2) yes C2 . Cl30 . 1.935(3) yes C2 . Cl51 . 1.578(3) yes C2 . H21 . 0.956 no C2 . Cl31 . 1.692(2) yes C2 . Cl50 . 1.905(3) yes C2 . H22 . 0.956 no F7 . C8 . 1.351(2) yes C8 . C9 . 1.383(2) yes C8 . C17 . 1.386(3) yes C9 . C10 . 1.509(2) yes C9 . C13 . 1.394(2) yes C10 . O11 . 1.246(2) yes C10 . O12 . 1.2561(19) yes C13 . F14 . 1.347(3) yes C13 . C15 . 1.373(3) yes C15 . C16 . 1.375(5) yes C15 . H151 . 0.962 no C16 . C17 . 1.379(4) yes C16 . H161 . 0.973 no C17 . H171 . 0.977 no O18 . C19 . 1.335(2) yes O18 . C28 . 1.451(2) yes C19 . O20 . 1.208(2) yes C19 . C21 . 1.507(2) yes C21 . C22 . 1.558(2) yes C21 . C25 . 1.5531(19) yes C21 . H211 . 0.993 no C22 . C23 . 1.522(2) yes C22 . C27 . 1.523(2) yes C22 . H221 . 1.007 no C23 . C24 . 1.526(3) yes C23 . H232 . 1.012 no C23 . H231 . 0.984 no C24 . C25 . 1.535(2) yes C24 . H242 . 0.971 no C24 . H241 . 1.001 no C25 . N26 . 1.4903(18) yes C25 . H251 . 0.993 no N26 . H262 . 0.904 no N26 . H261 . 0.925 no N26 . H263 . 0.907 no C27 . H271 . 1.003 no C27 . H272 . 1.007 no C27 . H273 . 0.966 no C28 . H283 . 0.978 no C28 . H282 . 0.977 no C28 . H281 . 1.004 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 . C2 . Cl30 . 101.28(14) yes Cl1 . C2 . Cl51 . 115.28(15) yes Cl30 . C2 . Cl51 . 110.76(17) yes Cl1 . C2 . H21 . 109.6 no Cl30 . C2 . H21 . 109.0 no Cl51 . C2 . H21 . 110.4 no Cl1 . C2 . Cl31 . 115.52(15) yes Cl1 . C2 . Cl50 . 106.94(13) yes Cl31 . C2 . Cl50 . 105.71(14) yes Cl1 . C2 . H22 . 109.6 no Cl31 . C2 . H22 . 109.1 no Cl50 . C2 . H22 . 109.9 no F7 . C8 . C9 . 118.26(14) yes F7 . C8 . C17 . 118.06(17) yes C9 . C8 . C17 . 123.66(19) yes C8 . C9 . C10 . 123.09(14) yes C8 . C9 . C13 . 114.93(17) yes C10 . C9 . C13 . 121.98(16) yes C9 . C10 . O11 . 117.20(14) yes C9 . C10 . O12 . 117.28(13) yes O11 . C10 . O12 . 125.51(15) yes C9 . C13 . F14 . 118.61(18) yes C9 . C13 . C15 . 123.7(2) yes F14 . C13 . C15 . 117.7(2) yes C13 . C15 . C16 . 118.5(2) yes C13 . C15 . H151 . 120.9 no C16 . C15 . H151 . 120.6 no C15 . C16 . C17 . 121.0(2) yes C15 . C16 . H161 . 117.5 no C17 . C16 . H161 . 121.5 no C8 . C17 . C16 . 118.2(2) yes C8 . C17 . H171 . 119.8 no C16 . C17 . H171 . 122.0 no C19 . O18 . C28 . 116.21(16) yes O18 . C19 . O20 . 124.23(15) yes O18 . C19 . C21 . 111.19(13) yes O20 . C19 . C21 . 124.53(15) yes C19 . C21 . C22 . 109.89(12) yes C19 . C21 . C25 . 110.74(12) yes C22 . C21 . C25 . 104.10(11) yes C19 . C21 . H211 . 109.6 no C22 . C21 . H211 . 111.8 no C25 . C21 . H211 . 110.6 no C21 . C22 . C23 . 103.43(12) yes C21 . C22 . C27 . 115.28(14) yes C23 . C22 . C27 . 114.21(15) yes C21 . C22 . H221 . 105.9 no C23 . C22 . H221 . 107.1 no C27 . C22 . H221 . 110.3 no C22 . C23 . C24 . 103.11(13) yes C22 . C23 . H232 . 107.2 no C24 . C23 . H232 . 113.4 no C22 . C23 . H231 . 111.1 no C24 . C23 . H231 . 112.8 no H232 . C23 . H231 . 109.0 no C23 . C24 . C25 . 104.42(14) yes C23 . C24 . H242 . 113.9 no C25 . C24 . H242 . 111.5 no C23 . C24 . H241 . 108.7 no C25 . C24 . H241 . 108.4 no H242 . C24 . H241 . 109.8 no C24 . C25 . C21 . 106.95(12) yes C24 . C25 . N26 . 110.65(13) yes C21 . C25 . N26 . 111.38(11) yes C24 . C25 . H251 . 111.9 no C21 . C25 . H251 . 107.6 no N26 . C25 . H251 . 108.3 no C25 . N26 . H262 . 110.9 no C25 . N26 . H261 . 110.2 no H262 . N26 . H261 . 108.9 no C25 . N26 . H263 . 107.9 no H262 . N26 . H263 . 109.4 no H261 . N26 . H263 . 109.5 no C22 . C27 . H271 . 111.3 no C22 . C27 . H272 . 109.1 no H271 . C27 . H272 . 105.7 no C22 . C27 . H273 . 112.3 no H271 . C27 . H273 . 110.2 no H272 . C27 . H273 . 108.0 no O18 . C28 . H283 . 105.4 no O18 . C28 . H282 . 107.9 no H283 . C28 . H282 . 110.5 no O18 . C28 . H281 . 110.2 no H283 . C28 . H281 . 110.2 no H282 . C28 . H281 . 112.3 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 C24 . H242 . O18 1_565 160.27(5) 0.971 2.458 3.387(3) yes C28 . H282 . O20 4_547 128.64(7) 0.977 2.548 3.249(3) yes N26 . H262 . O11 . 173.64(5) 0.904 1.869 2.769(3) yes N26 . H261 . O12 1_565 162.94(5) 0.925 1.848 2.746(3) yes N26 . H263 . O12 4_556 171.33(5) 0.907 1.872 2.772(3) yes C2 . H21 . O11 . 151.14(16) 0.956 2.186 3.058(3) yes C2 . H22 . O11 . 147.33(13) 0.956 2.209 3.058(3) yes _iucr_refine_instruction_details_constraints ; # # Punched on 17/04/13 at 17:28:54 # #LIST 12 BLOCK SCALE X'S, U'S CONT ENANTIO RIDE C ( 15,X'S) H ( 151,X'S) RIDE C ( 16,X'S) H ( 161,X'S) RIDE C ( 17,X'S) H ( 171,X'S) RIDE C ( 21,X'S) H ( 211,X'S) RIDE C ( 22,X'S) H ( 221,X'S) RIDE C ( 23,X'S) H ( 232,X'S) H ( 231,X'S) RIDE C ( 24,X'S) H ( 242,X'S) H ( 241,X'S) RIDE C ( 25,X'S) H ( 251,X'S) RIDE N ( 26,X'S) H ( 262,X'S) H ( 261,X'S) H ( 263,X'S) RIDE C ( 27,X'S) H ( 271,X'S) H ( 272,X'S) H ( 273,X'S) RIDE C ( 28,X'S) H ( 283,X'S) H ( 282,X'S) H ( 281,X'S) EQUIV PART (1001,OCC) PART (1002, OCC) WEIGHT -1 PART (1002,OCC) END ; _iucr_refine_instruction_details_restraints ; # # Punched on 17/04/13 at 17:28:54 # #LIST 16 NO REM HREST START (DO NOT REMOVE THIS LINE) REM HREST END (DO NOT REMOVE THIS LINE) END ; _database_code_depnum_ccdc_archive 'CCDC 936130' ####################################################################### # # Cambridge Crystallographic Data Centre # CCDC # ####################################################################### # # This CIF contains data from an original supplementary publication # deposited with the CCDC, and may include chemical, crystal, # experimental, refinement, atomic coordinates, # anisotropic displacement parameters and molecular geometry data, # as required by the journal to which it was submitted. # # This CIF is provided on the understanding that it is used for bona # fide research purposes only. It may contain copyright material # of the CCDC or of third parties, and may not be copied or further # disseminated in any form, whether machine-readable or not, # except for the purpose of generating routine backup copies # on your local computer system. # # For further information on the CCDC, data deposition and # data retrieval see: # www.ccdc.cam.ac.uk # # Bona fide researchers may freely download Mercury and enCIFer # from this site to visualise CIF-encoded structures and # to carry out CIF format checking respectively. # data_30.HBF4 _ccdc_journal_depnumber ? #============================================================================== _cell_length_a 5.5150(2) _cell_length_b 7.6423(3) _cell_length_c 17.2563(6) _cell_angle_alpha 90 _cell_angle_beta 90.531(3) _cell_angle_gamma 90 _cell_volume 727.27(5) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 21 1' _symmetry_space_group_name_Hall 'P 2yb' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,y+1/2,-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' B 0.0090 0.0039 2.0545 23.2185 1.3326 1.0210 1.0979 60.3498 0.7068 0.1403 -0.1932 'International Tables Vol C 4.2.6.8 and 6.1.1.4' F 0.0727 0.0534 3.5392 10.2825 2.6412 4.2944 1.5170 0.2615 1.0243 26.1476 0.2776 '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' 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' _cell_formula_units_Z 2 # Given Formula = C13 H18 B1 F4 N1 O2 # Dc = 1.40 Fooo = 320.00 Mu = 10.99 M = 307.09 # Found Formula = C13 H18 B1 F4 N1 O2 # Dc = 1.40 FOOO = 320.00 Mu = 10.99 M = 307.09 _chemical_formula_sum 'C13 H18 B1 F4 N1 O2' _chemical_formula_moiety 'C13 H18 B1 F4 N1 O2' _chemical_compound_source . _chemical_formula_weight 307.09 _cell_measurement_reflns_used 2014 _cell_measurement_theta_min 5 _cell_measurement_theta_max 76 _cell_measurement_temperature 150 _exptl_crystal_description block _exptl_crystal_colour colourless _exptl_crystal_size_min 0.220 _exptl_crystal_size_mid 0.230 _exptl_crystal_size_max 0.270 _exptl_crystal_density_diffrn 1.402 _exptl_crystal_density_meas . _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 320 _exptl_absorpt_coefficient_mu 1.099 # Sheldrick geometric approximatio 0.78 0.79 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'CrysAlis, (Oxford Diffraction, 2002)' _exptl_absorpt_correction_T_min 0.73 _exptl_absorpt_correction_T_max 0.79 _diffrn_measurement_device_type 'Oxford Diffraction SuperNova' _diffrn_measurement_device Area _diffrn_radiation_monochromator graphite _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 'SuperNova, (Oxford Diffraction, 2010)' _computing_cell_refinement 'CrysAlis, (Oxford Diffraction, 2002)' _computing_data_reduction 'CrysAlis, (Oxford Diffraction, 2002)' _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 3004 _reflns_number_total 2045 _diffrn_reflns_av_R_equivalents 0.012 # Number of reflections without Friedels Law is 2045 # Number of reflections with Friedels Law is 1500 # Theoretical number of reflections is about 1523 _diffrn_reflns_theta_min 5.126 _diffrn_reflns_theta_max 76.203 _diffrn_measured_fraction_theta_max 0.920 _diffrn_reflns_theta_full 26.671 _diffrn_measured_fraction_theta_full 0.929 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -9 _diffrn_reflns_limit_k_max 7 _diffrn_reflns_limit_l_min -12 _diffrn_reflns_limit_l_max 21 _reflns_limit_h_min -6 _reflns_limit_h_max 6 _reflns_limit_k_min -9 _reflns_limit_k_max 7 _reflns_limit_l_min 0 _reflns_limit_l_max 21 _oxford_diffrn_Wilson_B_factor 2.52 _oxford_diffrn_Wilson_scale 0.00 _atom_sites_solution_primary Direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_diff_density_min -0.18 _refine_diff_density_max 0.22 # 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 2038 _refine_ls_number_restraints 1 _refine_ls_number_parameters 191 _oxford_refine_ls_R_factor_ref 0.0362 _refine_ls_wR_factor_ref 0.0921 _refine_ls_goodness_of_fit_ref 1.0004 _refine_ls_shift/su_max 0.0001332 _refine_ls_shift/su_mean 0.0000137 # The values computed from all data _oxford_reflns_number_all 2038 _refine_ls_R_factor_all 0.0362 _refine_ls_wR_factor_all 0.0921 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 1978 _refine_ls_R_factor_gt 0.0352 _refine_ls_wR_factor_gt 0.0912 _refine_ls_abs_structure_Flack -0.03(16) _refine_ls_abs_structure_details 'Flack (1983), 545 Friedel-pairs' # 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 ad _refine_ls_structure_factor_coef Fsqd _refine_ls_matrix_type full _refine_ls_hydrogen_treatment constr # none, 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^) + ( 0.05P)^2^ + 0.27P] ,where P=(max(Fo^2^,0) + 2Fc^2^)/3 ; # 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 F1 F 0.5149(3) 0.6596(2) 0.09458(9) 0.0454 1.0000 Uani . . . . . . B2 B 0.4946(4) 0.8287(4) 0.06579(14) 0.0302 1.0000 Uani . . . . . . F3 F 0.2677(3) 0.8437(3) 0.03319(12) 0.0673 1.0000 Uani . . . . . . F4 F 0.5113(4) 0.9488(3) 0.12428(12) 0.0751 1.0000 Uani . . . . . . F5 F 0.6740(5) 0.8521(3) 0.01272(15) 0.0972 1.0000 Uani . . . . . . O6 O 0.5052(2) 0.5889(2) 0.26989(8) 0.0254 1.0000 Uani . . . . . . C7 C 0.2836(3) 0.5849(3) 0.23750(10) 0.0213 1.0000 Uani . . . . . . O8 O 0.1434(3) 0.7051(2) 0.23897(9) 0.0299 1.0000 Uani . . . . . . C9 C 0.2337(3) 0.4128(3) 0.19843(10) 0.0211 1.0000 Uani . . . . . . C10 C 0.2169(4) 0.2471(3) 0.25218(12) 0.0252 1.0000 Uani . . . . . . C11 C 0.2033(4) 0.2893(3) 0.33755(11) 0.0256 1.0000 Uani . . . . . . C12 C 0.0120(4) 0.3858(3) 0.36780(13) 0.0324 1.0000 Uani . . . . . . C13 C 0.0068(5) 0.4340(3) 0.44490(14) 0.0392 1.0000 Uani . . . . . . C14 C 0.1966(5) 0.3848(4) 0.49454(13) 0.0437 1.0000 Uani . . . . . . C15 C 0.3848(5) 0.2864(4) 0.46557(14) 0.0423 1.0000 Uani . . . . . . C16 C 0.3887(4) 0.2382(3) 0.38791(14) 0.0356 1.0000 Uani . . . . . . C17 C -0.0063(4) 0.1450(3) 0.22000(13) 0.0345 1.0000 Uani . . . . . . C18 C -0.0605(4) 0.2225(3) 0.13988(13) 0.0317 1.0000 Uani . . . . . . C19 C -0.0084(3) 0.4144(3) 0.15423(10) 0.0220 1.0000 Uani . . . . . . N20 N 0.0035(3) 0.5222(2) 0.08210(9) 0.0248 1.0000 Uani . . . . . . C21 C 0.5699(4) 0.7529(3) 0.30598(14) 0.0347 1.0000 Uani . . . . . . H91 H 0.3600 0.3956 0.1606 0.0265 1.0000 Uiso R . . . . . H101 H 0.3649 0.1729 0.2431 0.0324 1.0000 Uiso R . . . . . H121 H -0.1238 0.4183 0.3323 0.0405 1.0000 Uiso R . . . . . H131 H -0.1226 0.4996 0.4650 0.0471 1.0000 Uiso R . . . . . H141 H 0.1973 0.4169 0.5482 0.0504 1.0000 Uiso R . . . . . H151 H 0.5095 0.2502 0.5002 0.0555 1.0000 Uiso R . . . . . H161 H 0.5234 0.1702 0.3673 0.0435 1.0000 Uiso R . . . . . H171 H -0.1419 0.1667 0.2542 0.0421 1.0000 Uiso R . . . . . H172 H 0.0301 0.0190 0.2176 0.0419 1.0000 Uiso R . . . . . H181 H -0.2280 0.2020 0.1228 0.0411 1.0000 Uiso R . . . . . H182 H 0.0520 0.1773 0.0995 0.0409 1.0000 Uiso R . . . . . H191 H -0.1324 0.4645 0.1899 0.0274 1.0000 Uiso R . . . . . H211 H 0.7316 0.7431 0.3303 0.0558 1.0000 Uiso R . . . . . H213 H 0.4513 0.7795 0.3466 0.0569 1.0000 Uiso R . . . . . H212 H 0.5727 0.8458 0.2660 0.0569 1.0000 Uiso R . . . . . H203 H 0.1231 0.4776 0.0511 0.0402 1.0000 Uiso R . . . . . H201 H -0.1390 0.5137 0.0574 0.0388 1.0000 Uiso R . . . . . H202 H 0.0336 0.6359 0.0948 0.0389 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 F1 0.0344(8) 0.0402(9) 0.0618(9) 0.0216(7) 0.0062(6) 0.0050(6) B2 0.0289(12) 0.0293(13) 0.0323(12) 0.0070(10) -0.0010(9) -0.0037(10) F3 0.0599(10) 0.0489(11) 0.0924(14) 0.0185(10) -0.0403(10) -0.0003(9) F4 0.0969(15) 0.0621(13) 0.0660(11) -0.0163(10) -0.0013(10) -0.0342(11) F5 0.1073(17) 0.0720(16) 0.1137(17) 0.0337(13) 0.0771(14) 0.0034(14) O6 0.0243(7) 0.0237(7) 0.0281(6) -0.0025(6) -0.0055(5) -0.0004(6) C7 0.0232(9) 0.0193(9) 0.0212(8) 0.0025(7) 0.0012(6) -0.0013(8) O8 0.0277(8) 0.0189(7) 0.0431(8) -0.0031(6) -0.0030(6) 0.0027(6) C9 0.0197(9) 0.0178(9) 0.0260(8) 0.0010(7) 0.0004(6) 0.0007(8) C10 0.0271(10) 0.0170(10) 0.0317(10) 0.0028(8) 0.0025(8) 0.0023(8) C11 0.0273(10) 0.0192(10) 0.0305(10) 0.0056(8) 0.0017(7) -0.0003(8) C12 0.0350(11) 0.0279(12) 0.0344(10) 0.0050(9) 0.0028(8) 0.0037(9) C13 0.0472(14) 0.0331(13) 0.0376(11) 0.0038(10) 0.0103(9) 0.0043(11) C14 0.0593(16) 0.0426(15) 0.0292(10) 0.0057(10) -0.0007(10) -0.0094(13) C15 0.0424(13) 0.0512(16) 0.0333(11) 0.0123(11) -0.0053(10) -0.0047(12) C16 0.0316(12) 0.0378(13) 0.0373(11) 0.0118(10) 0.0008(9) 0.0022(10) C17 0.0401(13) 0.0210(10) 0.0423(12) 0.0017(9) 0.0004(10) -0.0082(9) C18 0.0346(12) 0.0224(10) 0.0378(11) -0.0033(9) -0.0022(9) -0.0076(9) C19 0.0201(9) 0.0201(9) 0.0257(8) -0.0004(7) 0.0012(6) -0.0008(8) N20 0.0230(8) 0.0241(9) 0.0273(8) -0.0006(6) -0.0033(6) -0.0007(7) C21 0.0369(12) 0.0304(12) 0.0368(11) -0.0083(9) -0.0068(9) -0.0054(10) _refine_ls_extinction_method None _oxford_refine_ls_scale 16.0(12) 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 F1 . B2 . 1.389(3) yes B2 . F3 . 1.372(3) yes B2 . F4 . 1.367(3) yes B2 . F5 . 1.366(3) yes O6 . C7 . 1.340(2) yes O6 . C21 . 1.442(3) yes C7 . O8 . 1.201(3) yes C7 . C9 . 1.502(3) yes C9 . C10 . 1.573(3) yes C9 . C19 . 1.531(2) yes C9 . H91 . 0.969 no C10 . C11 . 1.511(3) yes C10 . C17 . 1.556(3) yes C10 . H101 . 1.007 no C11 . C12 . 1.393(3) yes C11 . C16 . 1.392(3) yes C12 . C13 . 1.381(3) yes C12 . H121 . 0.995 no C13 . C14 . 1.398(4) yes C13 . H131 . 0.941 no C14 . C15 . 1.380(4) yes C14 . H141 . 0.958 no C15 . C16 . 1.390(4) yes C15 . H151 . 0.947 no C16 . H161 . 0.976 no C17 . C18 . 1.531(3) yes C17 . H171 . 0.971 no C17 . H172 . 0.984 no C18 . C19 . 1.514(3) yes C18 . H181 . 0.979 no C18 . H182 . 1.000 no C19 . N20 . 1.494(3) yes C19 . H191 . 1.001 no N20 . H203 . 0.919 no N20 . H201 . 0.893 no N20 . H202 . 0.912 no C21 . H211 . 0.985 no C21 . H213 . 0.985 no C21 . H212 . 0.990 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 F1 . B2 . F3 . 107.1(2) yes F1 . B2 . F4 . 110.9(2) yes F3 . B2 . F4 . 107.5(2) yes F1 . B2 . F5 . 107.8(2) yes F3 . B2 . F5 . 112.2(2) yes F4 . B2 . F5 . 111.3(2) yes C7 . O6 . C21 . 114.90(16) yes O6 . C7 . O8 . 123.95(19) yes O6 . C7 . C9 . 111.74(17) yes O8 . C7 . C9 . 124.31(17) yes C7 . C9 . C10 . 116.86(15) yes C7 . C9 . C19 . 111.84(16) yes C10 . C9 . C19 . 104.15(15) yes C7 . C9 . H91 . 106.9 no C10 . C9 . H91 . 109.6 no C19 . C9 . H91 . 107.1 no C9 . C10 . C11 . 113.99(16) yes C9 . C10 . C17 . 104.11(15) yes C11 . C10 . C17 . 114.14(18) yes C9 . C10 . H101 . 108.0 no C11 . C10 . H101 . 108.7 no C17 . C10 . H101 . 107.6 no C10 . C11 . C12 . 121.56(18) yes C10 . C11 . C16 . 120.4(2) yes C12 . C11 . C16 . 118.0(2) yes C11 . C12 . C13 . 121.6(2) yes C11 . C12 . H121 . 118.0 no C13 . C12 . H121 . 120.3 no C12 . C13 . C14 . 119.8(2) yes C12 . C13 . H131 . 121.3 no C14 . C13 . H131 . 118.9 no C13 . C14 . C15 . 119.1(2) yes C13 . C14 . H141 . 121.3 no C15 . C14 . H141 . 119.6 no C14 . C15 . C16 . 120.8(2) yes C14 . C15 . H151 . 118.3 no C16 . C15 . H151 . 120.8 no C11 . C16 . C15 . 120.6(2) yes C11 . C16 . H161 . 118.6 no C15 . C16 . H161 . 120.7 no C10 . C17 . C18 . 105.99(18) yes C10 . C17 . H171 . 108.0 no C18 . C17 . H171 . 109.7 no C10 . C17 . H172 . 110.1 no C18 . C17 . H172 . 112.2 no H171 . C17 . H172 . 110.6 no C17 . C18 . C19 . 101.07(17) yes C17 . C18 . H181 . 112.6 no C19 . C18 . H181 . 112.4 no C17 . C18 . H182 . 112.3 no C19 . C18 . H182 . 109.3 no H181 . C18 . H182 . 108.9 no C9 . C19 . C18 . 103.72(16) yes C9 . C19 . N20 . 111.99(15) yes C18 . C19 . N20 . 114.03(16) yes C9 . C19 . H191 . 107.1 no C18 . C19 . H191 . 110.0 no N20 . C19 . H191 . 109.7 no C19 . N20 . H203 . 108.5 no C19 . N20 . H201 . 108.2 no H203 . N20 . H201 . 109.2 no C19 . N20 . H202 . 109.5 no H203 . N20 . H202 . 111.4 no H201 . N20 . H202 . 109.9 no O6 . C21 . H211 . 109.7 no O6 . C21 . H213 . 108.9 no H211 . C21 . H213 . 108.4 no O6 . C21 . H212 . 109.1 no H211 . C21 . H212 . 109.3 no H213 . C21 . H212 . 111.3 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 C17 . H172 . O8 1_545 168.77(6) 0.984 2.506 3.477(3) yes _iucr_refine_instruction_details_constraints ; # # Punched on 02/04/13 at 16:16:44 # #LIST 12 BLOCK SCALE X'S, U'S CONT ENANTIO RIDE C ( 9,X'S) H ( 91,X'S) RIDE C ( 10,X'S) H ( 101,X'S) RIDE C ( 12,X'S) H ( 121,X'S) RIDE C ( 13,X'S) H ( 131,X'S) RIDE C ( 14,X'S) H ( 141,X'S) RIDE C ( 15,X'S) H ( 151,X'S) RIDE C ( 16,X'S) H ( 161,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) RIDE N ( 20,X'S) H ( 203,X'S) H ( 201,X'S) H ( 202,X'S) RIDE C ( 21,X'S) H ( 211,X'S) H ( 213,X'S) H ( 212,X'S) END ; _iucr_refine_instruction_details_restraints ; # # Punched on 02/04/13 at 16:16:44 # #LIST 16 NO REM HREST START (DO NOT REMOVE THIS LINE) REM HREST END (DO NOT REMOVE THIS LINE) END ; _database_code_depnum_ccdc_archive 'CCDC 936131'