# Electronic Supplementary Material (ESI) for Dalton Transactions # 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_1 _audit_creation_date 11-09-15 _audit_creation_method CRYSTALS_ver_14.11 _oxford_structure_analysis_title 'P21n in P2(1)/n' _chemical_name_systematic ? _chemical_melting_point ? # Hand-made tables can be put in the cif. The number of columns # is set in the loop header. # The contants of each column can either be a piece of text # without any spaces (eg a number) or other text enclosed in " " # Remove the leading # in the following example #geom_extra_table_head_A #; #Table 2. #Molecular parameters deviating most from MOGUL averages #; # #loop_ #_geom_extra_tableA_col_1 #_geom_extra_tableA_col_2 #_geom_extra_tableA_col_3 #_geom_extra_tableA_col_4 # #Parameter "Observed Value" "MOGUL Value" "MOGUL e.s.d" #N5-C6-C4 129 124 "7 (\%)" #C3-O10-C2 105 109 "2 (\%)" #C6-O7 1.25 1.22 ".02 (\%A)" # #data_1 _exptl_special_details ; The crystal was placed in the cold stream of an Oxford Cryosystems open-flow nitrogen cryostat (Cosier & Glazer, 1986) with a nominal stability of 0.1K. Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105 107. ; _refine_special_details ; ? ; #--------------------------------------------------------------- # _oxford_ data items, April 2010: # There is some uncertainty about the correct way of forming local data # names, e.g. # _atom_site_special_shape_oxford # or # _oxford_atom_site_special_shape # see: # http://www.iucr.org/resources/cif/spec/version1.1/semantics#namespace # A reserved prefix, e.g. foo, must be used in the following way # " If the data file contains items defined in a DDL1 dictionary, the # local data names assigned under the reserved prefix must contain it as # their first component, e.g. _foo_atom_site_my_item. " # However, this seems to say the opposite: # http://www.iucr.org/__data/iucr/cif/standard/cifstd8.html # According to advice from the IUCr, CRYSTALS is correct #--------------------------------------------------------------- # End of 'script/refcif.dat' #end of refcif _cell_length_a 9.767(2) _cell_length_b 13.621(3) _cell_length_c 15.317(3) _cell_angle_alpha 90 _cell_angle_beta 101.51(3) _cell_angle_gamma 90 _cell_volume 1996.7(7) _symmetry_cell_setting Monoclinic _symmetry_space_group_name_H-M 'P 1 21/n 1 ' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z -x+1/2,y+1/2,-z+1/2 x+1/2,-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' B 0.0013 0.0007 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 0.0061 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' 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' S 0.1246 0.1234 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' _cell_formula_units_Z 4 # Given Formula = C25 H18 B1 N1 O1 S1 # Dc = 1.30 Fooo = 816.00 Mu = 1.78 M = 391.30 # Found Formula = C25 H18 B1 N1 O1 S1 # Dc = 1.30 FOOO = 816.00 Mu = 1.78 M = 391.30 _chemical_formula_sum 'C25 H18 B1 N1 O1 S1' _chemical_formula_moiety 'C25 H18 B1 N1 O1 S1' _chemical_compound_source ? _chemical_formula_weight 391.30 _cell_measurement_reflns_used 25 _cell_measurement_theta_min 15 _cell_measurement_theta_max 18 _cell_measurement_temperature 298 _exptl_crystal_description block _exptl_crystal_colour green _exptl_crystal_size_min 0.400 _exptl_crystal_size_mid 0.500 _exptl_crystal_size_max 0.600 _exptl_crystal_density_diffrn 1.302 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 816 _exptl_absorpt_coefficient_mu 0.178 # Sheldrick geometric approximatio 0.91 0.93 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_process_details '(North et al., 1968)' _exptl_absorpt_correction_T_min 0.68 _exptl_absorpt_correction_T_max 0.93 _diffrn_measurement_device_type Four-circle _diffrn_measurement_device 'Rigaku AFC-7R' _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _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 150 _diffrn_standards_number 3 _diffrn_standards_decay_% 0.00 _diffrn_ambient_temperature 298 _diffrn_reflns_number 4788 _reflns_number_total 4585 _diffrn_reflns_av_R_equivalents 0.000 # Number of reflections without Friedels Law is 4585 # Number of reflections with Friedels Law is 0 # Theoretical number of reflections is about 4589 _diffrn_reflns_theta_min 2.019 _diffrn_reflns_theta_max 27.504 _diffrn_measured_fraction_theta_max 1.000 _diffrn_reflns_theta_full 27.504 _diffrn_measured_fraction_theta_full 1.000 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -17 _diffrn_reflns_limit_k_max 0 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 19 _reflns_limit_h_min -12 _reflns_limit_h_max 12 _reflns_limit_k_min 0 _reflns_limit_k_max 17 _reflns_limit_l_min 0 _reflns_limit_l_max 19 _oxford_diffrn_Wilson_B_factor 3.93 _oxford_diffrn_Wilson_scale 6.64 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.41 _refine_diff_density_max 0.49 # 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>-10.0\s(I) _refine_ls_number_reflns 4569 _refine_ls_number_restraints 126 _refine_ls_number_parameters 317 _oxford_refine_ls_R_factor_ref 0.0823 _refine_ls_wR_factor_ref 0.1904 _refine_ls_goodness_of_fit_ref 0.9973 _refine_ls_shift/su_max 0.0017875 _refine_ls_shift/su_mean 0.0001002 # The values computed from all data _oxford_reflns_number_all 4569 _refine_ls_R_factor_all 0.0823 _refine_ls_wR_factor_all 0.1904 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 3237 _refine_ls_R_factor_gt 0.0577 _refine_ls_wR_factor_gt 0.1478 # 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: 29.7 46.2 22.1 5.31 ; # 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 _atom_site_attached_hydrogens S1 S 0.93307(6) 0.34417(5) 0.58609(5) 0.0555 1.0000 Uani . . . . . . C13 C 1.1029(2) 0.36472(16) 0.57582(15) 0.0413 1.0000 Uani . . . . . . N1 N 1.1953(2) 0.35574(14) 0.65065(13) 0.0410 1.0000 Uani . . . . . . C14 C 1.1337(3) 0.32875(17) 0.72277(16) 0.0448 1.0000 Uani D . . . . . C19 C 0.9895(3) 0.32037(19) 0.69860(18) 0.0515 1.0000 Uani D . . . . . C18 C 0.9088(3) 0.2938(2) 0.7611(2) 0.0689 1.0000 Uani D . . . . . C17 C 0.9763(4) 0.2747(2) 0.8459(2) 0.0743 1.0000 Uani D . . . . . C16 C 1.1207(4) 0.2803(2) 0.8696(2) 0.0715 1.0000 Uani D . . . . . C15 C 1.2014(3) 0.3076(2) 0.80933(19) 0.0610 1.0000 Uani D . . . . . B1 B 1.3616(3) 0.3636(2) 0.64696(18) 0.0422 1.0000 Uani . . . . . . O1 O 1.36665(17) 0.43503(13) 0.57419(11) 0.0504 1.0000 Uani . . . . . . C21 C 1.2774(3) 0.42559(17) 0.49632(15) 0.0454 1.0000 Uani D . . . . . C20 C 1.1412(3) 0.39070(17) 0.49258(15) 0.0446 1.0000 Uani D . . . . . C25 C 1.0481(3) 0.3856(2) 0.41082(18) 0.0572 1.0000 Uani D . . . . . C24 C 1.0896(4) 0.4134(2) 0.33362(18) 0.0669 1.0000 Uani D . . . . . C23 C 1.2239(4) 0.4481(2) 0.33780(18) 0.0627 1.0000 Uani D . . . . . C22 C 1.3172(3) 0.45527(19) 0.41747(17) 0.0545 1.0000 Uani D . . . . . C1 C 1.4127(3) 0.25569(18) 0.62389(13) 0.0454 1.0000 Uani D . . . . . C2 C 1.3370(3) 0.1701(2) 0.62234(18) 0.0579 1.0000 Uani D . . . . . C3 C 1.3936(4) 0.0788(2) 0.60694(19) 0.0747 1.0000 Uani D . . . . . C4 C 1.5291(4) 0.0728(3) 0.59423(18) 0.0756 1.0000 Uani D . . . . . C5 C 1.6063(4) 0.1566(3) 0.59485(19) 0.0739 1.0000 Uani D . . . . . C6 C 1.5483(3) 0.2465(2) 0.60808(17) 0.0592 1.0000 Uani D . . . . . C7 C 1.4483(2) 0.41097(17) 0.73793(15) 0.0427 1.0000 Uani D . . . . . C8 C 1.5439(3) 0.3572(2) 0.79939(17) 0.0510 1.0000 Uani D . . . . . C9 C 1.6128(3) 0.3964(2) 0.87947(18) 0.0625 1.0000 Uani D . . . . . C10 C 1.5895(3) 0.4917(3) 0.9007(2) 0.0675 1.0000 Uani D . . . . . C11 C 1.4990(3) 0.5475(2) 0.8410(2) 0.0726 1.0000 Uani D . . . . . C12 C 1.4298(3) 0.5082(2) 0.7607(2) 0.0587 1.0000 Uani D . . . . . H14 H 0.8120(19) 0.2898(8) 0.7440(13) 0.0895 1.0000 Uiso D . . . . . H13 H 0.925(2) 0.2570(8) 0.8884(12) 0.0885 1.0000 Uiso D . . . . . H12 H 1.164(2) 0.2653(8) 0.9288(12) 0.0900 1.0000 Uiso D . . . . . H11 H 1.3003(19) 0.3109(8) 0.8257(13) 0.0734 1.0000 Uiso D . . . . . H18 H 0.9584(18) 0.3628(8) 0.4081(12) 0.0685 1.0000 Uiso D . . . . . H17 H 1.0277(19) 0.4076(8) 0.2788(12) 0.0819 1.0000 Uiso D . . . . . H16 H 1.2517(19) 0.4678(8) 0.2851(12) 0.0750 1.0000 Uiso D . . . . . H15 H 1.4085(18) 0.4785(8) 0.4194(13) 0.0691 1.0000 Uiso D . . . . . H1 H 1.2449(18) 0.1732(14) 0.6316(7) 0.0676 1.0000 Uiso D . . . . . H2 H 1.3402(19) 0.0231(14) 0.6068(7) 0.0865 1.0000 Uiso D . . . . . H3 H 1.569(2) 0.0113(14) 0.5872(7) 0.0946 1.0000 Uiso D . . . . . H4 H 1.6998(19) 0.1531(15) 0.5867(7) 0.0870 1.0000 Uiso D . . . . . H5 H 1.6028(19) 0.3032(14) 0.6071(7) 0.0744 1.0000 Uiso D . . . . . H6 H 1.5608(14) 0.2929(12) 0.7869(11) 0.0583 1.0000 Uiso D . . . . . H7 H 1.6754(15) 0.3572(13) 0.9193(11) 0.0752 1.0000 Uiso D . . . . . H8 H 1.6349(15) 0.5175(14) 0.9549(11) 0.0792 1.0000 Uiso D . . . . . H9 H 1.4823(15) 0.6124(13) 0.8555(12) 0.0880 1.0000 Uiso D . . . . . H10 H 1.3712(14) 0.5473(13) 0.7203(11) 0.0707 1.0000 Uiso D . . . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 S1 0.0413(3) 0.0642(4) 0.0581(4) 0.0032(3) 0.0031(3) -0.0046(3) C13 0.0408(10) 0.0364(10) 0.0443(11) 0.0003(8) 0.0031(9) 0.0007(8) N1 0.0429(9) 0.0391(9) 0.0401(9) 0.0037(7) 0.0064(7) 0.0000(7) C14 0.0480(12) 0.0403(11) 0.0473(12) 0.0009(9) 0.0125(10) -0.0019(9) C19 0.0507(13) 0.0486(13) 0.0556(14) -0.0005(10) 0.0115(11) -0.0048(10) C18 0.0519(15) 0.083(2) 0.076(2) 0.0034(16) 0.0223(14) -0.0081(15) C17 0.077(2) 0.088(2) 0.0659(19) 0.0074(16) 0.0340(16) -0.0130(18) C16 0.076(2) 0.087(2) 0.0542(16) 0.0133(15) 0.0205(14) -0.0083(17) C15 0.0568(15) 0.0750(19) 0.0513(14) 0.0091(13) 0.0109(12) -0.0051(13) B1 0.0389(12) 0.0448(13) 0.0416(12) 0.0060(10) 0.0051(10) 0.0005(10) O1 0.0445(9) 0.0583(10) 0.0461(9) 0.0154(7) 0.0036(7) -0.0041(7) C21 0.0518(13) 0.0398(11) 0.0432(12) 0.0061(9) 0.0060(10) 0.0043(9) C20 0.0540(13) 0.0384(11) 0.0393(11) 0.0013(9) 0.0045(9) 0.0008(9) C25 0.0669(16) 0.0517(14) 0.0472(13) -0.0019(11) -0.0027(12) -0.0092(12) C24 0.096(2) 0.0610(16) 0.0375(12) -0.0011(11) -0.0025(13) -0.0075(15) C23 0.090(2) 0.0578(16) 0.0412(13) 0.0051(11) 0.0150(13) 0.0038(15) C22 0.0635(15) 0.0555(14) 0.0460(13) 0.0099(11) 0.0142(11) 0.0043(12) C1 0.0520(13) 0.0507(13) 0.0295(10) -0.0009(9) -0.0015(9) 0.0041(10) C2 0.0610(16) 0.0514(14) 0.0549(15) -0.0047(11) -0.0041(12) 0.0011(12) C3 0.099(3) 0.0489(15) 0.0630(18) -0.0117(13) -0.0149(17) 0.0015(15) C4 0.104(3) 0.070(2) 0.0446(14) -0.0170(13) -0.0051(15) 0.0327(19) C5 0.080(2) 0.085(2) 0.0576(17) -0.0019(15) 0.0177(15) 0.0300(18) C6 0.0622(16) 0.0646(17) 0.0516(14) -0.0003(12) 0.0134(12) 0.0118(13) C7 0.0422(11) 0.0414(11) 0.0442(11) 0.0017(9) 0.0081(9) -0.0020(9) C8 0.0531(13) 0.0483(13) 0.0480(13) -0.0007(10) 0.0018(10) -0.0015(10) C9 0.0587(16) 0.0766(19) 0.0475(14) -0.0020(13) -0.0009(12) -0.0054(14) C10 0.0613(16) 0.078(2) 0.0600(17) -0.0220(15) 0.0051(13) -0.0148(15) C11 0.0741(19) 0.0534(16) 0.090(2) -0.0290(16) 0.0160(17) -0.0078(14) C12 0.0569(15) 0.0475(14) 0.0696(17) -0.0013(12) 0.0074(13) 0.0019(11) _refine_ls_extinction_coef 97(18) _refine_ls_extinction_method 'Larson (1970), Equation 22' _oxford_refine_ls_scale 0.4163(11) 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 S1 . C13 . 1.720(2) yes S1 . C19 . 1.732(3) yes C13 . N1 . 1.315(3) yes C13 . C20 . 1.443(3) yes N1 . C14 . 1.408(3) yes N1 . B1 . 1.640(3) yes C14 . C19 . 1.388(4) yes C14 . C15 . 1.389(4) yes C19 . C18 . 1.404(4) yes C18 . C17 . 1.359(5) yes C18 . H14 . 0.931(18) no C17 . C16 . 1.386(5) yes C17 . H13 . 0.931(17) no C16 . C15 . 1.379(4) yes C16 . H12 . 0.943(18) no C15 . H11 . 0.949(17) no B1 . O1 . 1.488(3) yes B1 . C1 . 1.614(4) yes B1 . C7 . 1.614(3) yes O1 . C21 . 1.336(3) yes C21 . C20 . 1.403(3) yes C21 . C22 . 1.400(3) yes C20 . C25 . 1.395(3) yes C25 . C24 . 1.378(4) yes C25 . H18 . 0.922(17) no C24 . C23 . 1.383(5) yes C24 . H17 . 0.935(17) no C23 . C22 . 1.373(4) yes C23 . H16 . 0.941(17) no C22 . H15 . 0.941(17) no C1 . C2 . 1.378(4) yes C1 . C6 . 1.399(4) yes C2 . C3 . 1.400(4) yes C2 . H1 . 0.939(17) no C3 . C4 . 1.378(5) yes C3 . H2 . 0.920(18) no C4 . C5 . 1.367(5) yes C4 . H3 . 0.939(18) no C5 . C6 . 1.380(4) yes C5 . H4 . 0.948(18) no C6 . H5 . 0.940(17) no C7 . C8 . 1.394(3) yes C7 . C12 . 1.390(4) yes C8 . C9 . 1.384(4) yes C8 . H6 . 0.919(17) no C9 . C10 . 1.368(5) yes C9 . H7 . 0.940(17) no C10 . C11 . 1.368(5) yes C10 . H8 . 0.929(18) no C11 . C12 . 1.388(4) yes C11 . H9 . 0.934(18) no C12 . H10 . 0.924(17) 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 C13 . S1 . C19 . 90.01(12) yes S1 . C13 . N1 . 114.30(18) yes S1 . C13 . C20 . 123.07(17) yes N1 . C13 . C20 . 122.6(2) yes C13 . N1 . C14 . 112.5(2) yes C13 . N1 . B1 . 118.41(19) yes C14 . N1 . B1 . 128.69(18) yes N1 . C14 . C19 . 112.4(2) yes N1 . C14 . C15 . 127.4(2) yes C19 . C14 . C15 . 120.1(2) yes S1 . C19 . C14 . 110.8(2) yes S1 . C19 . C18 . 128.0(2) yes C14 . C19 . C18 . 121.2(3) yes C19 . C18 . C17 . 118.0(3) yes C19 . C18 . H14 . 120.0(12) no C17 . C18 . H14 . 122.0(12) no C18 . C17 . C16 . 121.0(3) yes C18 . C17 . H13 . 119.5(12) no C16 . C17 . H13 . 119.6(12) no C17 . C16 . C15 . 121.8(3) yes C17 . C16 . H12 . 118.4(12) no C15 . C16 . H12 . 119.8(12) no C14 . C15 . C16 . 117.9(3) yes C14 . C15 . H11 . 120.5(12) no C16 . C15 . H11 . 121.6(12) no N1 . B1 . O1 . 104.44(17) yes N1 . B1 . C1 . 107.47(19) yes O1 . B1 . C1 . 111.9(2) yes N1 . B1 . C7 . 110.41(19) yes O1 . B1 . C7 . 107.16(19) yes C1 . B1 . C7 . 114.93(18) yes B1 . O1 . C21 . 119.53(19) yes O1 . C21 . C20 . 120.9(2) yes O1 . C21 . C22 . 119.9(2) yes C20 . C21 . C22 . 119.1(2) yes C13 . C20 . C21 . 117.3(2) yes C13 . C20 . C25 . 122.9(2) yes C21 . C20 . C25 . 119.8(2) yes C20 . C25 . C24 . 120.4(3) yes C20 . C25 . H18 . 120.1(12) no C24 . C25 . H18 . 119.5(12) no C25 . C24 . C23 . 119.5(3) yes C25 . C24 . H17 . 119.9(12) no C23 . C24 . H17 . 120.6(12) no C24 . C23 . C22 . 121.3(3) yes C24 . C23 . H16 . 119.4(12) no C22 . C23 . H16 . 119.2(12) no C21 . C22 . C23 . 119.8(3) yes C21 . C22 . H15 . 119.6(12) no C23 . C22 . H15 . 120.6(12) no B1 . C1 . C2 . 125.8(2) yes B1 . C1 . C6 . 117.7(2) yes C2 . C1 . C6 . 116.4(3) yes C1 . C2 . C3 . 121.7(3) yes C1 . C2 . H1 . 119.1(12) no C3 . C2 . H1 . 119.1(12) no C2 . C3 . C4 . 119.9(3) yes C2 . C3 . H2 . 119.4(12) no C4 . C3 . H2 . 120.7(12) no C3 . C4 . C5 . 119.6(3) yes C3 . C4 . H3 . 120.0(12) no C5 . C4 . H3 . 120.4(12) no C4 . C5 . C6 . 120.0(3) yes C4 . C5 . H4 . 120.1(12) no C6 . C5 . H4 . 119.9(12) no C1 . C6 . C5 . 122.4(3) yes C1 . C6 . H5 . 119.1(12) no C5 . C6 . H5 . 118.5(12) no B1 . C7 . C8 . 122.6(2) yes B1 . C7 . C12 . 121.7(2) yes C8 . C7 . C12 . 115.7(2) yes C7 . C8 . C9 . 122.5(3) yes C7 . C8 . H6 . 119.0(11) no C9 . C8 . H6 . 118.5(11) no C8 . C9 . C10 . 120.1(3) yes C8 . C9 . H7 . 119.6(12) no C10 . C9 . H7 . 120.3(12) no C9 . C10 . C11 . 119.0(3) yes C9 . C10 . H8 . 119.9(12) no C11 . C10 . H8 . 121.1(12) no C10 . C11 . C12 . 120.9(3) yes C10 . C11 . H9 . 119.1(12) no C12 . C11 . H9 . 120.0(12) no C7 . C12 . C11 . 121.7(3) yes C7 . C12 . H10 . 118.4(12) no C11 . C12 . H10 . 119.9(12) 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 C15 . H11 . C7 . 122.7(14) 0.949(17) 2.555(18) 3.170(4) yes C15 . H11 . C8 . 153.6(15) 0.949(17) 2.569(18) 3.445(4) yes C22 . H15 . O1 2_866 171.2(8) 0.941(17) 2.477(18) 3.410(4) yes _iucr_refine_instruction_details_constraints ; # # Punched on 15/09/11 at 22:55:32 # #LIST 12 BLOCK CONT SCALE CONT S ( 1 ,X'S,U'S) UNTIL C ( 12 ) CONT H ( 14 ,X'S) UNTIL H ( 10 ) CONT EXTPARAM END ; _iucr_refine_instruction_details_restraints ; # # Punched on 15/09/11 at 22:55:32 # #LIST 16 NO REM HREST START (DO NOT REMOVE THIS LINE) REM NO H NO #H U MULT DIST REM C-H REM >4 1.5 .96 DISORDER REM 1 1 1.2 .93 C C-H (ACETYLENE) REM 1 2 1.2 .93 C-C(H)-C REM 1 3 1.2 .98 (C)3-C-H REM 2 1 1.2 .93 C=C-H(2) REM 2 2 1.2 .97 (C)2-C-(H)2 REM 3 1 1.5 .96 C-C-(H)3 REM N-H REM >4 1.5 .89 DISORDER REM 1 1 1.2 .86 N-N/H REM 1 2 1.2 .86 (C)2-N-H REM 1 3 1.2 .89 (C)3-N-H REM 2 1 1.2 .86 C-N-(H)2 REM 2 2 1.2 .89 (C)2-N-(H)2 REM 3 1 1.2 .89 C-H-(H)3 REM O-H REM 1 1 1.5 .82 O-H REM REM DIST ESD = 0.02 REM VIB ESD = 0.002 REM ANGLE ESD = 2.0 REM 1 H ON SP 2 DIST 0.93, 0.02 = CONT C ( 18) TO H(14) REST 0.083, 0.002 = H(14,U[ISO]) ANGLE 0.0, 2.0 = MEAN CONT H(14) TO C ( 18) TO C(19) CONT H(14) TO C ( 18) TO C(17) PLANAR C ( 18) C(19) C(17) H(14) REM 1 H ON SP 2 DIST 0.93, 0.02 = CONT C ( 17) TO H(13) REST 0.089, 0.002 = H(13,U[ISO]) ANGLE 0.0, 2.0 = MEAN CONT H(13) TO C ( 17) TO C(18) CONT H(13) TO C ( 17) TO C(16) PLANAR C ( 17) C(18) C(16) H(13) REM 1 H ON SP 2 DIST 0.93, 0.02 = CONT C ( 16) TO H(12) REST 0.086, 0.002 = H(12,U[ISO]) ANGLE 0.0, 2.0 = MEAN CONT H(12) TO C ( 16) TO C(17) CONT H(12) TO C ( 16) TO C(15) PLANAR C ( 16) C(17) C(15) H(12) REM 1 H ON SP 2 DIST 0.93, 0.02 = CONT C ( 15) TO H(11) REST 0.072, 0.002 = H(11,U[ISO]) ANGLE 0.0, 2.0 = MEAN CONT H(11) TO C ( 15) TO C(14) CONT H(11) TO C ( 15) TO C(16) PLANAR C ( 15) C(14) C(16) H(11) REM 1 H ON SP 2 DIST 0.93, 0.02 = CONT C ( 25) TO H(18) REST 0.068, 0.002 = H(18,U[ISO]) ANGLE 0.0, 2.0 = MEAN CONT H(18) TO C ( 25) TO C(20) CONT H(18) TO C ( 25) TO C(24) PLANAR C ( 25) C(20) C(24) H(18) REM 1 H ON SP 2 DIST 0.93, 0.02 = CONT C ( 24) TO H(17) REST 0.080, 0.002 = H(17,U[ISO]) ANGLE 0.0, 2.0 = MEAN CONT H(17) TO C ( 24) TO C(25) CONT H(17) TO C ( 24) TO C(23) PLANAR C ( 24) C(25) C(23) H(17) REM 1 H ON SP 2 DIST 0.93, 0.02 = CONT C ( 23) TO H(16) REST 0.075, 0.002 = H(16,U[ISO]) ANGLE 0.0, 2.0 = MEAN CONT H(16) TO C ( 23) TO C(24) CONT H(16) TO C ( 23) TO C(22) PLANAR C ( 23) C(24) C(22) H(16) REM 1 H ON SP 2 DIST 0.93, 0.02 = CONT C ( 22) TO H(15) REST 0.066, 0.002 = H(15,U[ISO]) ANGLE 0.0, 2.0 = MEAN CONT H(15) TO C ( 22) TO C(21) CONT H(15) TO C ( 22) TO C(23) PLANAR C ( 22) C(21) C(23) H(15) REM 1 H ON SP 2 DIST 0.93, 0.02 = CONT C ( 2) TO H(1) REST 0.070, 0.002 = H(1,U[ISO]) ANGLE 0.0, 2.0 = MEAN CONT H(1) TO C ( 2) TO C(1) CONT H(1) TO C ( 2) TO C(3) PLANAR C ( 2) C(1) C(3) H(1) REM 1 H ON SP 2 DIST 0.93, 0.02 = CONT C ( 3) TO H(2) REST 0.090, 0.002 = H(2,U[ISO]) ANGLE 0.0, 2.0 = MEAN CONT H(2) TO C ( 3) TO C(2) CONT H(2) TO C ( 3) TO C(4) PLANAR C ( 3) C(2) C(4) H(2) REM 1 H ON SP 2 DIST 0.93, 0.02 = CONT C ( 4) TO H(3) REST 0.090, 0.002 = H(3,U[ISO]) ANGLE 0.0, 2.0 = MEAN CONT H(3) TO C ( 4) TO C(3) CONT H(3) TO C ( 4) TO C(5) PLANAR C ( 4) C(3) C(5) H(3) REM 1 H ON SP 2 DIST 0.93, 0.02 = CONT C ( 5) TO H(4) REST 0.089, 0.002 = H(4,U[ISO]) ANGLE 0.0, 2.0 = MEAN CONT H(4) TO C ( 5) TO C(4) CONT H(4) TO C ( 5) TO C(6) PLANAR C ( 5) C(4) C(6) H(4) REM 1 H ON SP 2 DIST 0.93, 0.02 = CONT C ( 6) TO H(5) REST 0.072, 0.002 = H(5,U[ISO]) ANGLE 0.0, 2.0 = MEAN CONT H(5) TO C ( 6) TO C(1) CONT H(5) TO C ( 6) TO C(5) PLANAR C ( 6) C(1) C(5) H(5) REM 1 H ON SP 2 DIST 0.93, 0.02 = CONT C ( 8) TO H(6) REST 0.061, 0.002 = H(6,U[ISO]) ANGLE 0.0, 2.0 = MEAN CONT H(6) TO C ( 8) TO C(7) CONT H(6) TO C ( 8) TO C(9) PLANAR C ( 8) C(7) C(9) H(6) REM 1 H ON SP 2 DIST 0.93, 0.02 = CONT C ( 9) TO H(7) REST 0.076, 0.002 = H(7,U[ISO]) ANGLE 0.0, 2.0 = MEAN CONT H(7) TO C ( 9) TO C(8) CONT H(7) TO C ( 9) TO C(10) PLANAR C ( 9) C(8) C(10) H(7) REM 1 H ON SP 2 DIST 0.93, 0.02 = CONT C ( 10) TO H(8) REST 0.082, 0.002 = H(8,U[ISO]) ANGLE 0.0, 2.0 = MEAN CONT H(8) TO C ( 10) TO C(9) CONT H(8) TO C ( 10) TO C(11) PLANAR C ( 10) C(9) C(11) H(8) REM 1 H ON SP 2 DIST 0.93, 0.02 = CONT C ( 11) TO H(9) REST 0.088, 0.002 = H(9,U[ISO]) ANGLE 0.0, 2.0 = MEAN CONT H(9) TO C ( 11) TO C(10) CONT H(9) TO C ( 11) TO C(12) PLANAR C ( 11) C(10) C(12) H(9) REM 1 H ON SP 2 DIST 0.93, 0.02 = CONT C ( 12) TO H(10) REST 0.070, 0.002 = H(10,U[ISO]) ANGLE 0.0, 2.0 = MEAN CONT H(10) TO C ( 12) TO C(7) CONT H(10) TO C ( 12) TO C(11) PLANAR C ( 12) C(7) C(11) H(10) REM HREST END (DO NOT REMOVE THIS LINE) END ; _database_code_depnum_ccdc_archive 'CCDC 949536' ####################################################################### # # 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_2 #==================================================================== #data_New_Global_Publ_Block # start Validation Reply Form # start Validation Reply Form _vrf_PLAT601_I ; PROBLEM: Structure Contains Solvent Accessible VOIDS of . 218 A**3 RESPONSE: Severely disordered solvent (C6H6) molecule was squizzed. ; # end Validation Reply Form #==================================================================== #data_global _audit_creation_date 13-01-17 _audit_creation_method CRYSTALS_ver_14.40 _oxford_structure_analysis_title 'P21n_complete in P2(1)/n' _chemical_name_systematic ? _chemical_melting_point ? # Hand-made tables can be put in the cif. The number of columns # is set in the loop header. # The contants of each column can either be a piece of text # without any spaces (eg a number) or other text enclosed in " " # Remove the leading # in the following example #geom_extra_table_head_A #; #Table 2. #Molecular parameters deviating most from MOGUL averages #; # #loop_ #_geom_extra_tableA_col_1 #_geom_extra_tableA_col_2 #_geom_extra_tableA_col_3 #_geom_extra_tableA_col_4 # #Parameter "Observed Value" "MOGUL Value" "MOGUL e.s.d" #N5-C6-C4 129 124 "7 (\%)" #C3-O10-C2 105 109 "2 (\%)" #C6-O7 1.25 1.22 ".02 (\%A)" # #data_1 _exptl_special_details ; The crystal was placed in the cold stream of an Oxford Cryosystems open-flow nitrogen cryostat (Cosier & Glazer, 1986) with a nominal stability of 0.1K. Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105-107. ; _refine_special_details ; ? ; #--------------------------------------------------------------- # _oxford_ data items, April 2010: # There is some uncertainty about the correct way of forming local data # names, e.g. # _atom_site_special_shape_oxford # or # _oxford_atom_site_special_shape # see: # http://www.iucr.org/resources/cif/spec/version1.1/semantics#namespace # A reserved prefix, e.g. foo, must be used in the following way # " If the data file contains items defined in a DDL1 dictionary, the # local data names assigned under the reserved prefix must contain it as # their first component, e.g. _foo_atom_site_my_item. " # However, this seems to say the opposite: # http://www.iucr.org/__data/iucr/cif/standard/cifstd8.html # According to advice from the IUCr, CRYSTALS is correct #--------------------------------------------------------------- # End of 'script/refcif.dat' #end of refcif _cell_length_a 10.551(2) _cell_length_b 12.434(3) _cell_length_c 17.889(4) _cell_angle_alpha 90 _cell_angle_beta 104.88(3) _cell_angle_gamma 90 _cell_volume 2268.2(8) _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/n 1 ' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z -x+1/2,y+1/2,-z+1/2 x+1/2,-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' B 0.0013 0.0007 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 0.0061 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' 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 4 # Given Formula = C28 H20 B1 N1 O2 # Dc = 1.21 Fooo = 784.00 Mu = 0.75 M = 413.28 # Found Formula = C25 H18 B1 N1 O2 # Dc = 1.10 FOOO = 784.00 Mu = 0.69 M = 375.23 _chemical_formula_sum 'C25 H18 B1 N1 O2' _chemical_formula_moiety 'C25 H18 B1 N1 O2' _chemical_compound_source ? _chemical_formula_weight 375.23 _cell_measurement_reflns_used 25 _cell_measurement_theta_min 15 _cell_measurement_theta_max 18 _cell_measurement_temperature 298 _exptl_crystal_description needle _exptl_crystal_colour yellow _exptl_crystal_size_min 0.200 _exptl_crystal_size_mid 0.250 _exptl_crystal_size_max 0.300 _exptl_crystal_density_diffrn 1.099 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 784 _exptl_absorpt_coefficient_mu 0.069 # Sheldrick geometric approximatio 0.98 0.99 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_process_details '(North et al., 1968)' _exptl_absorpt_correction_T_min 0.95 _exptl_absorpt_correction_T_max 0.99 _diffrn_measurement_device_type Unknown _diffrn_measurement_device Serial _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _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 150 _diffrn_standards_number 3 _diffrn_standards_decay_% 0.00 _diffrn_ambient_temperature 298 _diffrn_reflns_number 5182 _reflns_number_total 5182 _diffrn_reflns_av_R_equivalents 0.000 # Number of reflections without Friedels Law is 5182 # Number of reflections with Friedels Law is 0 # Theoretical number of reflections is about 5257 _diffrn_reflns_theta_min 2.566 _diffrn_reflns_theta_max 27.588 _diffrn_measured_fraction_theta_max 0.987 _diffrn_reflns_theta_full 27.036 _diffrn_measured_fraction_theta_full 0.996 _diffrn_reflns_limit_h_min -13 _diffrn_reflns_limit_h_max 13 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 16 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 23 _reflns_limit_h_min -13 _reflns_limit_h_max 13 _reflns_limit_k_min 0 _reflns_limit_k_max 16 _reflns_limit_l_min 0 _reflns_limit_l_max 23 _oxford_diffrn_Wilson_B_factor 4.02 _oxford_diffrn_Wilson_scale 47.11 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_diff_density_min -0.63 _refine_diff_density_max 0.54 # 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>-10.0\s(I) _refine_ls_number_reflns 5164 _refine_ls_number_restraints 0 _refine_ls_number_parameters 262 _oxford_refine_ls_R_factor_ref 0.1838 _refine_ls_wR_factor_ref 0.2473 _refine_ls_goodness_of_fit_ref 1.0689 _refine_ls_shift/su_max 0.0001418 _refine_ls_shift/su_mean 0.0000130 # The values computed with all filters except I/sigma _oxford_reflns_number_all 5164 _refine_ls_R_factor_all 0.1838 _refine_ls_wR_factor_all 0.2473 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 1641 _refine_ls_R_factor_gt 0.0618 _refine_ls_wR_factor_gt 0.1497 # 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, 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: 7.55 10.2 2.86 ; # 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 O2 O 0.1202(3) 0.4188(2) 0.41021(13) 0.0675 1.0000 Uani . . . . . . C13 C 0.1565(4) 0.3914(3) 0.4852(2) 0.0618 1.0000 Uani . . . . . . N1 N 0.1662(3) 0.2881(2) 0.49756(15) 0.0599 1.0000 Uani . . . . . . C14 C 0.1334(4) 0.2390(3) 0.4246(2) 0.0648 1.0000 Uani . . . . . . C19 C 0.1049(4) 0.3227(3) 0.3707(2) 0.0682 1.0000 Uani . . . . . . C18 C 0.0635(5) 0.3054(4) 0.2917(2) 0.0841 1.0000 Uani . . . . . . C17 C 0.0546(5) 0.1998(5) 0.2690(2) 0.0909 1.0000 Uani . . . . . . C16 C 0.0859(5) 0.1153(4) 0.3217(2) 0.0901 1.0000 Uani . . . . . . C15 C 0.1253(4) 0.1334(4) 0.4004(2) 0.0783 1.0000 Uani . . . . . . B1 B 0.1908(4) 0.2405(3) 0.5848(2) 0.0610 1.0000 Uani . . . . . . O1 O 0.2712(3) 0.3278(2) 0.63367(13) 0.0686 1.0000 Uani . . . . . . C21 C 0.2431(4) 0.4323(3) 0.6198(2) 0.0627 1.0000 Uani . . . . . . C20 C 0.1844(4) 0.4715(3) 0.5458(2) 0.0636 1.0000 Uani . . . . . . C25 C 0.1608(4) 0.5808(3) 0.5320(2) 0.0736 1.0000 Uani . . . . . . C24 C 0.1919(4) 0.6507(3) 0.5927(3) 0.0806 1.0000 Uani . . . . . . C23 C 0.2491(4) 0.6127(4) 0.6665(3) 0.0834 1.0000 Uani . . . . . . C22 C 0.2768(4) 0.5056(3) 0.6807(2) 0.0757 1.0000 Uani . . . . . . C7 C 0.2796(4) 0.1345(3) 0.59433(18) 0.0598 1.0000 Uani . . . . . . C8 C 0.2419(5) 0.0385(3) 0.6216(2) 0.0754 1.0000 Uani . . . . . . C9 C 0.3237(6) -0.0515(4) 0.6340(3) 0.0971 1.0000 Uani . . . . . . C10 C 0.4435(6) -0.0472(4) 0.6179(3) 0.0941 1.0000 Uani . . . . . . C11 C 0.4797(5) 0.0464(5) 0.5899(3) 0.0920 1.0000 Uani . . . . . . C12 C 0.3999(4) 0.1350(4) 0.5793(2) 0.0782 1.0000 Uani . . . . . . C1 C 0.0508(4) 0.2292(3) 0.60375(19) 0.0633 1.0000 Uani . . . . . . C6 C -0.0509(4) 0.1671(3) 0.5585(2) 0.0697 1.0000 Uani . . . . . . C5 C -0.1715(5) 0.1558(4) 0.5739(3) 0.0812 1.0000 Uani . . . . . . C4 C -0.1927(5) 0.2074(4) 0.6374(3) 0.0892 1.0000 Uani . . . . . . C3 C -0.0954(5) 0.2685(4) 0.6843(3) 0.0945 1.0000 Uani . . . . . . C2 C 0.0235(4) 0.2797(3) 0.6670(2) 0.0765 1.0000 Uani . . . . . . H14 H 0.0427 0.3638 0.2565 0.0976 1.0000 Uiso R . . . . . H13 H 0.0272 0.1855 0.2155 0.1026 1.0000 Uiso R . . . . . H11 H 0.1455 0.0772 0.4371 0.0959 1.0000 Uiso R . . . . . H18 H 0.1265 0.6049 0.4812 0.0906 1.0000 Uiso R . . . . . H17 H 0.1726 0.7242 0.5841 0.0917 1.0000 Uiso R . . . . . H16 H 0.2695 0.6614 0.7082 0.1045 1.0000 Uiso R . . . . . H15 H 0.3168 0.4800 0.7317 0.0940 1.0000 Uiso R . . . . . H6 H 0.1603 0.0345 0.6333 0.0951 1.0000 Uiso R . . . . . H7 H 0.2937 -0.1140 0.6528 0.1128 1.0000 Uiso R . . . . . H8 H 0.4985 -0.1080 0.6263 0.1129 1.0000 Uiso R . . . . . H9 H 0.5621 0.0484 0.5794 0.1147 1.0000 Uiso R . . . . . H10 H 0.4293 0.1986 0.5606 0.1019 1.0000 Uiso R . . . . . H5 H -0.0357 0.1303 0.5150 0.0818 1.0000 Uiso R . . . . . H4 H -0.2382 0.1118 0.5426 0.1018 1.0000 Uiso R . . . . . H3 H -0.2763 0.2017 0.6482 0.1127 1.0000 Uiso R . . . . . H2 H -0.1105 0.3023 0.7281 0.1116 1.0000 Uiso R . . . . . H1 H 0.0890 0.3237 0.6984 0.1010 1.0000 Uiso R . . . . . H12 H 0.0798 0.0449 0.3036 0.1037 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 O2 0.0787(17) 0.0686(16) 0.0500(13) 0.0112(12) 0.0071(12) -0.0072(13) C13 0.061(2) 0.068(2) 0.0513(19) 0.0076(17) 0.0056(16) -0.0069(18) N1 0.0721(18) 0.0545(17) 0.0460(14) 0.0045(13) 0.0020(13) -0.0073(14) C14 0.068(2) 0.073(3) 0.0472(19) -0.0003(17) 0.0038(15) -0.0097(18) C19 0.075(2) 0.076(3) 0.051(2) 0.0057(19) 0.0103(17) -0.005(2) C18 0.093(3) 0.105(4) 0.049(2) 0.009(2) 0.0084(19) -0.008(3) C17 0.102(3) 0.110(4) 0.053(2) -0.011(2) 0.006(2) -0.015(3) C16 0.109(4) 0.091(3) 0.060(2) -0.015(2) 0.006(2) -0.011(3) C15 0.093(3) 0.077(3) 0.058(2) -0.0023(19) 0.007(2) -0.009(2) B1 0.071(2) 0.059(2) 0.0422(19) 0.0070(17) -0.0033(17) -0.006(2) O1 0.0805(17) 0.0639(16) 0.0502(13) 0.0014(11) -0.0038(12) -0.0059(13) C21 0.064(2) 0.060(2) 0.057(2) 0.0018(17) 0.0032(17) -0.0092(17) C20 0.068(2) 0.060(2) 0.058(2) 0.0038(16) 0.0062(17) -0.0071(17) C25 0.080(3) 0.062(3) 0.074(2) 0.003(2) 0.009(2) -0.012(2) C24 0.084(3) 0.063(3) 0.088(3) 0.003(2) 0.010(2) -0.004(2) C23 0.085(3) 0.073(3) 0.084(3) -0.021(2) 0.008(2) -0.012(2) C22 0.082(3) 0.076(3) 0.060(2) -0.006(2) -0.0002(19) -0.010(2) C7 0.069(2) 0.061(2) 0.0454(17) -0.0020(15) 0.0061(15) -0.0026(17) C8 0.094(3) 0.062(2) 0.065(2) 0.0144(19) 0.013(2) 0.002(2) C9 0.135(5) 0.057(3) 0.088(3) 0.013(2) 0.010(3) 0.009(3) C10 0.108(4) 0.088(4) 0.079(3) -0.010(3) 0.011(3) 0.023(3) C11 0.077(3) 0.108(4) 0.090(3) -0.008(3) 0.020(2) 0.011(3) C12 0.081(3) 0.072(3) 0.076(3) 0.001(2) 0.010(2) -0.005(2) C1 0.079(2) 0.056(2) 0.0507(19) 0.0103(16) 0.0083(17) -0.0004(18) C6 0.072(2) 0.063(2) 0.067(2) 0.0024(18) 0.0074(19) -0.0034(19) C5 0.076(3) 0.077(3) 0.086(3) 0.001(2) 0.013(2) -0.008(2) C4 0.076(3) 0.103(4) 0.093(3) -0.001(3) 0.031(2) -0.005(3) C3 0.103(4) 0.113(4) 0.072(3) -0.005(3) 0.030(3) 0.001(3) C2 0.088(3) 0.083(3) 0.056(2) -0.0006(19) 0.0123(19) -0.002(2) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.1931(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 O2 . C13 . 1.342(4) yes O2 . C19 . 1.377(5) yes C13 . N1 . 1.303(5) yes C13 . C20 . 1.445(5) yes N1 . C14 . 1.402(4) yes N1 . B1 . 1.626(4) yes C14 . C19 . 1.398(5) yes C14 . C15 . 1.378(6) yes C19 . C18 . 1.385(5) yes C18 . C17 . 1.370(7) yes C18 . H14 . 0.949 no C17 . C16 . 1.393(7) yes C17 . H13 . 0.943 no C16 . C15 . 1.381(6) yes C16 . H12 . 0.930 no C15 . H11 . 0.945 no B1 . O1 . 1.510(5) yes B1 . C7 . 1.600(6) yes B1 . C1 . 1.605(6) yes O1 . C21 . 1.342(4) yes C21 . C20 . 1.397(5) yes C21 . C22 . 1.395(5) yes C20 . C25 . 1.392(5) yes C25 . C24 . 1.363(6) yes C25 . H18 . 0.937 no C24 . C23 . 1.387(6) yes C24 . H17 . 0.939 no C23 . C22 . 1.373(6) yes C23 . H16 . 0.942 no C22 . H15 . 0.955 no C7 . C8 . 1.385(5) yes C7 . C12 . 1.364(6) yes C8 . C9 . 1.395(6) yes C8 . H6 . 0.939 no C9 . C10 . 1.368(8) yes C9 . H7 . 0.935 no C10 . C11 . 1.359(7) yes C10 . H8 . 0.941 no C11 . C12 . 1.370(6) yes C11 . H9 . 0.936 no C12 . H10 . 0.941 no C1 . C6 . 1.399(5) yes C1 . C2 . 1.387(5) yes C6 . C5 . 1.376(6) yes C6 . H5 . 0.951 no C5 . C4 . 1.373(7) yes C5 . H4 . 0.952 no C4 . C3 . 1.376(7) yes C4 . H3 . 0.953 no C3 . C2 . 1.374(6) yes C3 . H2 . 0.938 no C2 . H1 . 0.945 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 C13 . O2 . C19 . 105.0(3) yes O2 . C13 . N1 . 114.2(3) yes O2 . C13 . C20 . 121.7(3) yes N1 . C13 . C20 . 124.1(3) yes C13 . N1 . C14 . 106.4(3) yes C13 . N1 . B1 . 120.5(3) yes C14 . N1 . B1 . 132.5(3) yes N1 . C14 . C19 . 106.0(3) yes N1 . C14 . C15 . 133.4(3) yes C19 . C14 . C15 . 120.6(3) yes C14 . C19 . O2 . 108.4(3) yes C14 . C19 . C18 . 122.9(4) yes O2 . C19 . C18 . 128.6(4) yes C19 . C18 . C17 . 115.5(4) yes C19 . C18 . H14 . 121.1 no C17 . C18 . H14 . 123.4 no C18 . C17 . C16 . 122.4(4) yes C18 . C17 . H13 . 117.4 no C16 . C17 . H13 . 120.2 no C17 . C16 . C15 . 121.6(5) yes C17 . C16 . H12 . 119.4 no C15 . C16 . H12 . 119.0 no C16 . C15 . C14 . 116.9(4) yes C16 . C15 . H11 . 122.9 no C14 . C15 . H11 . 120.2 no N1 . B1 . O1 . 102.8(3) yes N1 . B1 . C7 . 110.3(3) yes O1 . B1 . C7 . 107.7(3) yes N1 . B1 . C1 . 107.8(3) yes O1 . B1 . C1 . 110.6(3) yes C7 . B1 . C1 . 116.8(3) yes B1 . O1 . C21 . 121.6(3) yes O1 . C21 . C20 . 122.4(3) yes O1 . C21 . C22 . 119.2(3) yes C20 . C21 . C22 . 118.4(4) yes C13 . C20 . C21 . 115.2(3) yes C13 . C20 . C25 . 123.2(3) yes C21 . C20 . C25 . 121.6(4) yes C20 . C25 . C24 . 119.1(4) yes C20 . C25 . H18 . 119.4 no C24 . C25 . H18 . 121.4 no C25 . C24 . C23 . 119.8(4) yes C25 . C24 . H17 . 119.5 no C23 . C24 . H17 . 120.7 no C24 . C23 . C22 . 121.8(4) yes C24 . C23 . H16 . 119.3 no C22 . C23 . H16 . 118.9 no C21 . C22 . C23 . 119.3(4) yes C21 . C22 . H15 . 119.4 no C23 . C22 . H15 . 121.3 no B1 . C7 . C8 . 122.3(4) yes B1 . C7 . C12 . 121.7(3) yes C8 . C7 . C12 . 116.0(4) yes C7 . C8 . C9 . 121.7(5) yes C7 . C8 . H6 . 119.2 no C9 . C8 . H6 . 119.1 no C8 . C9 . C10 . 120.2(5) yes C8 . C9 . H7 . 118.2 no C10 . C9 . H7 . 121.7 no C9 . C10 . C11 . 118.2(5) yes C9 . C10 . H8 . 120.0 no C11 . C10 . H8 . 121.8 no C10 . C11 . C12 . 121.3(5) yes C10 . C11 . H9 . 117.4 no C12 . C11 . H9 . 121.3 no C11 . C12 . C7 . 122.6(4) yes C11 . C12 . H10 . 118.6 no C7 . C12 . H10 . 118.8 no B1 . C1 . C6 . 122.5(3) yes B1 . C1 . C2 . 121.9(4) yes C6 . C1 . C2 . 115.7(4) yes C1 . C6 . C5 . 123.5(4) yes C1 . C6 . H5 . 118.3 no C5 . C6 . H5 . 118.3 no C6 . C5 . C4 . 118.2(4) yes C6 . C5 . H4 . 121.5 no C4 . C5 . H4 . 120.2 no C5 . C4 . C3 . 120.6(4) yes C5 . C4 . H3 . 119.2 no C3 . C4 . H3 . 120.2 no C4 . C3 . C2 . 120.0(4) yes C4 . C3 . H2 . 119.7 no C2 . C3 . H2 . 120.3 no C1 . C2 . C3 . 122.0(4) yes C1 . C2 . H1 . 118.3 no C3 . C2 . H1 . 119.7 no _iucr_refine_instruction_details_constraints ; # # Punched on 17/01/13 at 21:25:21 # #LIST 12 BLOCK SCALE X'S, U'S RIDE C ( 18,X'S) H ( 14,X'S) RIDE C ( 17,X'S) H ( 13,X'S) RIDE C ( 16,X'S) H ( 12,X'S) RIDE C ( 15,X'S) H ( 11,X'S) RIDE C ( 25,X'S) H ( 18,X'S) RIDE C ( 24,X'S) H ( 17,X'S) RIDE C ( 23,X'S) H ( 16,X'S) RIDE C ( 22,X'S) H ( 15,X'S) RIDE C ( 8,X'S) H ( 6,X'S) RIDE C ( 9,X'S) H ( 7,X'S) RIDE C ( 10,X'S) H ( 8,X'S) RIDE C ( 11,X'S) H ( 9,X'S) RIDE C ( 12,X'S) H ( 10,X'S) RIDE C ( 6,X'S) H ( 5,X'S) RIDE C ( 5,X'S) H ( 4,X'S) RIDE C ( 4,X'S) H ( 3,X'S) RIDE C ( 3,X'S) H ( 2,X'S) RIDE C ( 2,X'S) H ( 1,X'S) END ; _iucr_refine_instruction_details_restraints ; # # Punched on 17/01/13 at 21:25:21 # #LIST 16 NO REM HREST START (DO NOT REMOVE THIS LINE) REM HREST END (DO NOT REMOVE THIS LINE) END ; # Manually omitted reflections loop_ _oxford_refln_omitted_index_h _oxford_refln_omitted_index_k _oxford_refln_omitted_index_l _oxford_refln_omitted_flag _oxford_refln_omitted_details -2 0 2 x . -2 1 1 x . _database_code_depnum_ccdc_archive 'CCDC 949537' ####################################################################### # # 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_3 #data_global _audit_creation_date 13-01-17 _audit_creation_method CRYSTALS_ver_14.40 _oxford_structure_analysis_title 'Pccn in Pccn' _chemical_name_systematic ? _chemical_melting_point ? # Hand-made tables can be put in the cif. The number of columns # is set in the loop header. # The contants of each column can either be a piece of text # without any spaces (eg a number) or other text enclosed in " " # Remove the leading # in the following example #geom_extra_table_head_A #; #Table 2. #Molecular parameters deviating most from MOGUL averages #; # #loop_ #_geom_extra_tableA_col_1 #_geom_extra_tableA_col_2 #_geom_extra_tableA_col_3 #_geom_extra_tableA_col_4 # #Parameter "Observed Value" "MOGUL Value" "MOGUL e.s.d" #N5-C6-C4 129 124 "7 (\%)" #C3-O10-C2 105 109 "2 (\%)" #C6-O7 1.25 1.22 ".02 (\%A)" # #data_1 _exptl_special_details ; The crystal was placed in the cold stream of an Oxford Cryosystems open-flow nitrogen cryostat (Cosier & Glazer, 1986) with a nominal stability of 0.1K. Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105-107. ; _refine_special_details ; ? ; #--------------------------------------------------------------- # _oxford_ data items, April 2010: # There is some uncertainty about the correct way of forming local data # names, e.g. # _atom_site_special_shape_oxford # or # _oxford_atom_site_special_shape # see: # http://www.iucr.org/resources/cif/spec/version1.1/semantics#namespace # A reserved prefix, e.g. foo, must be used in the following way # " If the data file contains items defined in a DDL1 dictionary, the # local data names assigned under the reserved prefix must contain it as # their first component, e.g. _foo_atom_site_my_item. " # However, this seems to say the opposite: # http://www.iucr.org/__data/iucr/cif/standard/cifstd8.html # According to advice from the IUCr, CRYSTALS is correct #--------------------------------------------------------------- # End of 'script/refcif.dat' #end of refcif _cell_length_a 30.418(6) _cell_length_b 9.1270(18) _cell_length_c 15.996(3) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 4440.9(15) _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P c c n ' _symmetry_space_group_name_Hall '-P 2ab 2ac' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z -x+1/2,y,z+1/2 x+1/2,-y,-z+1/2 x,-y+1/2,z+1/2 -x,y+1/2,-z+1/2 -x+1/2,-y+1/2,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 0.0033 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' B 0.0013 0.0007 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 0.0061 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' 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' S 0.1246 0.1234 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' _cell_formula_units_Z 8 # Given Formula = C29 H20 B1 N1 O1 S1 # Dc = 1.32 Fooo = 1840.00 Mu = 1.69 M = 441.36 # Found Formula = C29 H20 B1 N1 O1 S1 # Dc = 1.32 FOOO = 1840.00 Mu = 1.69 M = 441.36 _chemical_formula_sum 'C29 H20 B1 N1 O1 S1' _chemical_formula_moiety 'C29 H20 B1 N1 O1 S1' _chemical_compound_source ? _chemical_formula_weight 441.36 _cell_measurement_reflns_used 25 _cell_measurement_theta_min 15 _cell_measurement_theta_max 18 _cell_measurement_temperature 298 _exptl_crystal_description needle _exptl_crystal_colour yellow _exptl_crystal_size_min 0.100 _exptl_crystal_size_mid 0.150 _exptl_crystal_size_max 0.200 _exptl_crystal_density_diffrn 1.320 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 1840 _exptl_absorpt_coefficient_mu 0.169 # Sheldrick geometric approximatio 0.98 0.98 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_process_details '(North et al., 1968)' _exptl_absorpt_correction_T_min 0.94 _exptl_absorpt_correction_T_max 0.98 _diffrn_measurement_device_type Unknown _diffrn_measurement_device Serial _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _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 150 _diffrn_standards_number 3 _diffrn_standards_decay_% 0.00 _diffrn_ambient_temperature 298 _diffrn_reflns_number 12625 _reflns_number_total 5101 _diffrn_reflns_av_R_equivalents 0.142 # Number of reflections without Friedels Law is 5101 # Number of reflections with Friedels Law is 0 # Theoretical number of reflections is about 5102 _diffrn_reflns_theta_min 2.547 _diffrn_reflns_theta_max 27.503 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.503 _diffrn_measured_fraction_theta_full 0.999 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 39 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_l_min -20 _diffrn_reflns_limit_l_max 20 _reflns_limit_h_min 0 _reflns_limit_h_max 39 _reflns_limit_k_min 0 _reflns_limit_k_max 11 _reflns_limit_l_min 0 _reflns_limit_l_max 20 _oxford_diffrn_Wilson_B_factor 3.25 _oxford_diffrn_Wilson_scale 118.58 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_diff_density_min -0.95 _refine_diff_density_max 0.99 # 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>-10.0\s(I) _refine_ls_number_reflns 5080 _refine_ls_number_restraints 0 _refine_ls_number_parameters 298 _oxford_refine_ls_R_factor_ref 0.1608 _refine_ls_wR_factor_ref 0.1400 _refine_ls_goodness_of_fit_ref 1.1252 _refine_ls_shift/su_max 0.0002927 _refine_ls_shift/su_mean 0.0000269 # The values computed with all filters except I/sigma _oxford_reflns_number_all 5080 _refine_ls_R_factor_all 0.1608 _refine_ls_wR_factor_all 0.1400 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 1846 _refine_ls_R_factor_gt 0.0480 _refine_ls_wR_factor_gt 0.0749 # 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, 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: 1.55 1.49 0.260 ; # 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 S1 S 0.56978(4) 0.04403(15) 0.67238(9) 0.0590 1.0000 Uani . . . . . . C19 C 0.62440(15) 0.0057(5) 0.6489(3) 0.0483 1.0000 Uani . . . . . . C14 C 0.64250(14) -0.0844(5) 0.7093(3) 0.0420 1.0000 Uani . . . . . . N1 N 0.61263(11) -0.1228(4) 0.7726(2) 0.0412 1.0000 Uani . . . . . . C13 C 0.57354(14) -0.0606(5) 0.7617(3) 0.0455 1.0000 Uani . . . . . . C20 C 0.53780(13) -0.0805(5) 0.8195(3) 0.0463 1.0000 Uani . . . . . . C21 C 0.54309(13) -0.1816(5) 0.8822(3) 0.0431 1.0000 Uani . . . . . . O1 O 0.57922(9) -0.2635(3) 0.88903(19) 0.0494 1.0000 Uani . . . . . . B1 B 0.62335(15) -0.2158(6) 0.8568(3) 0.0422 1.0000 Uani . . . . . . C1 C 0.64870(13) -0.3658(4) 0.8336(3) 0.0385 1.0000 Uani . . . . . . C2 C 0.62694(15) -0.4762(5) 0.7913(3) 0.0522 1.0000 Uani . . . . . . C3 C 0.64737(19) -0.6045(6) 0.7674(3) 0.0669 1.0000 Uani . . . . . . C4 C 0.6904(2) -0.6267(6) 0.7870(3) 0.0695 1.0000 Uani . . . . . . C5 C 0.71310(16) -0.5219(6) 0.8304(4) 0.0659 1.0000 Uani . . . . . . C6 C 0.69234(14) -0.3943(5) 0.8538(3) 0.0531 1.0000 Uani . . . . . . C7 C 0.64678(13) -0.1089(5) 0.9228(3) 0.0409 1.0000 Uani . . . . . . C12 C 0.66427(14) 0.0280(5) 0.9046(3) 0.0471 1.0000 Uani . . . . . . C11 C 0.68374(15) 0.1145(6) 0.9650(3) 0.0567 1.0000 Uani . . . . . . C10 C 0.68613(15) 0.0683(6) 1.0460(3) 0.0552 1.0000 Uani . . . . . . C9 C 0.66883(17) -0.0655(6) 1.0665(3) 0.0621 1.0000 Uani . . . . . . C8 C 0.64994(16) -0.1525(5) 1.0060(3) 0.0566 1.0000 Uani . . . . . . C22 C 0.50855(14) -0.2076(5) 0.9407(3) 0.0441 1.0000 Uani . . . . . . C27 C 0.46928(14) -0.1251(5) 0.9327(3) 0.0498 1.0000 Uani . . . . . . C26 C 0.43530(15) -0.1493(6) 0.9910(3) 0.0623 1.0000 Uani . . . . . . C25 C 0.43989(16) -0.2503(7) 1.0530(4) 0.0691 1.0000 Uani . . . . . . C24 C 0.47833(16) -0.3311(6) 1.0609(4) 0.0669 1.0000 Uani . . . . . . C23 C 0.51212(15) -0.3093(5) 1.0059(3) 0.0562 1.0000 Uani . . . . . . C28 C 0.46544(15) -0.0208(6) 0.8681(3) 0.0641 1.0000 Uani . . . . . . C29 C 0.49827(15) 0.0013(6) 0.8131(3) 0.0615 1.0000 Uani . . . . . . C15 C 0.68679(15) -0.1212(5) 0.7048(3) 0.0503 1.0000 Uani . . . . . . C16 C 0.71100(16) -0.0689(5) 0.6390(3) 0.0584 1.0000 Uani . . . . . . C17 C 0.69217(18) 0.0179(6) 0.5780(3) 0.0628 1.0000 Uani . . . . . . C18 C 0.64846(17) 0.0573(5) 0.5824(3) 0.0596 1.0000 Uani . . . . . . H1 H 0.5965 -0.4640 0.7779 0.0647 1.0000 Uiso R . . . . . H2 H 0.6316 -0.6780 0.7385 0.0819 1.0000 Uiso R . . . . . H3 H 0.7052 -0.7138 0.7698 0.0839 1.0000 Uiso R . . . . . H4 H 0.7424 -0.5369 0.8447 0.0777 1.0000 Uiso R . . . . . H5 H 0.7082 -0.3232 0.8836 0.0658 1.0000 Uiso R . . . . . H10 H 0.6617 0.0637 0.8488 0.0548 1.0000 Uiso R . . . . . H9 H 0.6956 0.2062 0.9498 0.0674 1.0000 Uiso R . . . . . H8 H 0.6994 0.1263 1.0884 0.0690 1.0000 Uiso R . . . . . H7 H 0.6699 -0.0997 1.1225 0.0739 1.0000 Uiso R . . . . . H6 H 0.6386 -0.2443 1.0211 0.0686 1.0000 Uiso R . . . . . H241 H 0.4089 -0.0959 0.9855 0.0750 1.0000 Uiso R . . . . . H251 H 0.4173 -0.2638 1.0919 0.0836 1.0000 Uiso R . . . . . H261 H 0.4819 -0.4003 1.1036 0.0800 1.0000 Uiso R . . . . . H271 H 0.5382 -0.3618 1.0125 0.0672 1.0000 Uiso R . . . . . H281 H 0.4392 0.0339 0.8627 0.0766 1.0000 Uiso R . . . . . H291 H 0.4950 0.0722 0.7708 0.0725 1.0000 Uiso R . . . . . H301 H 0.7003 -0.1822 0.7460 0.0606 1.0000 Uiso R . . . . . H311 H 0.7414 -0.0933 0.6357 0.0673 1.0000 Uiso R . . . . . H321 H 0.7092 0.0508 0.5328 0.0784 1.0000 Uiso R . . . . . H331 H 0.6352 0.1175 0.5406 0.0736 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 S1 0.0550(7) 0.0580(8) 0.0640(8) 0.0157(7) -0.0142(7) 0.0044(6) C19 0.050(3) 0.045(3) 0.049(3) 0.003(2) -0.005(2) -0.003(2) C14 0.046(2) 0.033(2) 0.047(3) 0.000(2) -0.004(2) -0.005(2) N1 0.0364(19) 0.039(2) 0.048(2) 0.0051(18) -0.0036(17) 0.0016(17) C13 0.044(2) 0.036(2) 0.057(3) 0.000(2) -0.015(2) 0.005(2) C20 0.034(2) 0.048(3) 0.057(3) 0.001(2) -0.006(2) 0.0073(19) C21 0.034(2) 0.038(2) 0.058(3) -0.004(2) -0.003(2) 0.0000(19) O1 0.0359(15) 0.0442(17) 0.068(2) 0.0122(17) 0.0057(15) 0.0081(14) B1 0.031(2) 0.044(3) 0.052(3) 0.010(3) 0.002(2) 0.002(2) C1 0.036(2) 0.036(2) 0.043(2) 0.006(2) 0.002(2) 0.0011(18) C2 0.048(3) 0.048(3) 0.060(3) -0.001(3) -0.001(2) -0.002(2) C3 0.079(4) 0.048(3) 0.074(4) -0.006(3) 0.006(3) -0.001(3) C4 0.089(4) 0.049(3) 0.071(4) 0.010(3) 0.024(3) 0.020(3) C5 0.051(3) 0.067(4) 0.080(4) 0.013(3) 0.008(3) 0.021(3) C6 0.041(2) 0.052(3) 0.066(3) 0.000(3) -0.002(2) 0.006(2) C7 0.037(2) 0.036(2) 0.050(3) 0.002(2) 0.000(2) 0.0099(19) C12 0.046(2) 0.050(3) 0.045(3) 0.002(2) 0.009(2) -0.002(2) C11 0.055(3) 0.053(3) 0.062(3) -0.009(3) 0.006(3) -0.004(3) C10 0.055(3) 0.056(3) 0.054(3) -0.012(3) -0.008(2) 0.008(3) C9 0.082(4) 0.054(3) 0.051(3) 0.004(3) -0.012(3) 0.016(3) C8 0.070(3) 0.043(3) 0.057(3) 0.007(3) -0.005(3) 0.009(3) C22 0.035(2) 0.041(3) 0.056(3) -0.008(2) -0.002(2) -0.0018(19) C27 0.034(2) 0.053(3) 0.062(3) -0.012(3) -0.005(2) 0.006(2) C26 0.040(3) 0.064(3) 0.083(4) -0.017(3) 0.006(3) 0.010(3) C25 0.048(3) 0.075(4) 0.084(4) -0.004(4) 0.017(3) 0.002(3) C24 0.052(3) 0.069(4) 0.080(4) 0.008(3) 0.015(3) 0.007(3) C23 0.042(3) 0.054(3) 0.072(3) 0.009(3) 0.008(3) 0.003(2) C28 0.037(2) 0.072(4) 0.083(4) -0.003(3) -0.007(3) 0.023(3) C29 0.047(3) 0.066(3) 0.072(4) 0.013(3) -0.009(3) 0.019(2) C15 0.051(3) 0.047(3) 0.053(3) 0.008(2) 0.004(2) 0.002(2) C16 0.054(3) 0.054(3) 0.067(3) 0.010(3) 0.008(3) 0.006(3) C17 0.077(4) 0.054(3) 0.057(3) 0.007(3) 0.008(3) -0.009(3) C18 0.073(3) 0.052(3) 0.054(3) 0.008(3) -0.010(3) -0.003(3) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.10521(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 S1 . C19 . 1.739(5) yes S1 . C13 . 1.723(4) yes C19 . C14 . 1.383(6) yes C19 . C18 . 1.374(6) yes C14 . N1 . 1.405(5) yes C14 . C15 . 1.390(6) yes N1 . C13 . 1.329(5) yes N1 . B1 . 1.626(6) yes C13 . C20 . 1.439(6) yes C20 . C21 . 1.372(6) yes C20 . C29 . 1.419(6) yes C21 . O1 . 1.334(5) yes C21 . C22 . 1.427(6) yes O1 . B1 . 1.502(5) yes B1 . C1 . 1.615(6) yes B1 . C7 . 1.604(7) yes C1 . C2 . 1.383(6) yes C1 . C6 . 1.390(6) yes C2 . C3 . 1.379(6) yes C2 . H1 . 0.957 no C3 . C4 . 1.360(7) yes C3 . H2 . 0.945 no C4 . C5 . 1.369(7) yes C4 . H3 . 0.955 no C5 . C6 . 1.377(6) yes C5 . H4 . 0.931 no C6 . H5 . 0.939 no C7 . C12 . 1.389(6) yes C7 . C8 . 1.391(6) yes C12 . C11 . 1.382(6) yes C12 . H10 . 0.953 no C11 . C10 . 1.365(6) yes C11 . H9 . 0.942 no C10 . C9 . 1.369(7) yes C10 . H8 . 0.950 no C9 . C8 . 1.378(6) yes C9 . H7 . 0.949 no C8 . H6 . 0.938 no C22 . C27 . 1.418(6) yes C22 . C23 . 1.400(6) yes C27 . C26 . 1.409(6) yes C27 . C28 . 1.410(7) yes C26 . C25 . 1.361(7) yes C26 . H241 . 0.943 no C25 . C24 . 1.389(7) yes C25 . H251 . 0.935 no C24 . C23 . 1.368(6) yes C24 . H261 . 0.936 no C23 . H271 . 0.932 no C28 . C29 . 1.346(6) yes C28 . H281 . 0.944 no C29 . H291 . 0.941 no C15 . C16 . 1.370(6) yes C15 . H301 . 0.956 no C16 . C17 . 1.382(6) yes C16 . H311 . 0.952 no C17 . C18 . 1.379(7) yes C17 . H321 . 0.939 no C18 . H331 . 0.956 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 C19 . S1 . C13 . 90.2(2) yes S1 . C19 . C14 . 110.4(3) yes S1 . C19 . C18 . 127.4(4) yes C14 . C19 . C18 . 122.2(4) yes C19 . C14 . N1 . 113.2(4) yes C19 . C14 . C15 . 119.6(4) yes N1 . C14 . C15 . 127.1(4) yes C14 . N1 . C13 . 112.2(4) yes C14 . N1 . B1 . 126.7(3) yes C13 . N1 . B1 . 120.7(4) yes S1 . C13 . N1 . 113.9(3) yes S1 . C13 . C20 . 123.6(3) yes N1 . C13 . C20 . 122.5(4) yes C13 . C20 . C21 . 117.8(4) yes C13 . C20 . C29 . 121.8(4) yes C21 . C20 . C29 . 120.4(4) yes C20 . C21 . O1 . 122.2(4) yes C20 . C21 . C22 . 120.3(4) yes O1 . C21 . C22 . 117.4(4) yes C21 . O1 . B1 . 123.1(3) yes N1 . B1 . O1 . 104.8(3) yes N1 . B1 . C1 . 110.3(4) yes O1 . B1 . C1 . 105.1(3) yes N1 . B1 . C7 . 108.5(4) yes O1 . B1 . C7 . 110.4(4) yes C1 . B1 . C7 . 117.1(4) yes B1 . C1 . C2 . 120.1(4) yes B1 . C1 . C6 . 124.1(4) yes C2 . C1 . C6 . 115.8(4) yes C1 . C2 . C3 . 122.6(5) yes C1 . C2 . H1 . 119.2 no C3 . C2 . H1 . 118.2 no C2 . C3 . C4 . 119.7(5) yes C2 . C3 . H2 . 120.6 no C4 . C3 . H2 . 119.7 no C3 . C4 . C5 . 119.9(5) yes C3 . C4 . H3 . 120.8 no C5 . C4 . H3 . 119.3 no C4 . C5 . C6 . 119.8(5) yes C4 . C5 . H4 . 120.4 no C6 . C5 . H4 . 119.8 no C1 . C6 . C5 . 122.2(5) yes C1 . C6 . H5 . 118.7 no C5 . C6 . H5 . 119.1 no B1 . C7 . C12 . 125.4(4) yes B1 . C7 . C8 . 119.1(4) yes C12 . C7 . C8 . 115.6(4) yes C7 . C12 . C11 . 122.1(4) yes C7 . C12 . H10 . 118.3 no C11 . C12 . H10 . 119.6 no C12 . C11 . C10 . 120.7(5) yes C12 . C11 . H9 . 119.4 no C10 . C11 . H9 . 119.9 no C11 . C10 . C9 . 118.8(5) yes C11 . C10 . H8 . 121.9 no C9 . C10 . H8 . 119.3 no C10 . C9 . C8 . 120.4(5) yes C10 . C9 . H7 . 120.4 no C8 . C9 . H7 . 119.2 no C7 . C8 . C9 . 122.4(5) yes C7 . C8 . H6 . 118.4 no C9 . C8 . H6 . 119.2 no C21 . C22 . C27 . 118.2(4) yes C21 . C22 . C23 . 122.8(4) yes C27 . C22 . C23 . 119.0(4) yes C22 . C27 . C26 . 118.3(5) yes C22 . C27 . C28 . 119.7(4) yes C26 . C27 . C28 . 122.0(4) yes C27 . C26 . C25 . 120.9(5) yes C27 . C26 . H241 . 118.8 no C25 . C26 . H241 . 120.3 no C26 . C25 . C24 . 120.9(5) yes C26 . C25 . H251 . 119.9 no C24 . C25 . H251 . 119.2 no C25 . C24 . C23 . 119.8(5) yes C25 . C24 . H261 . 121.5 no C23 . C24 . H261 . 118.7 no C22 . C23 . C24 . 121.1(5) yes C22 . C23 . H271 . 119.5 no C24 . C23 . H271 . 119.4 no C27 . C28 . C29 . 121.2(4) yes C27 . C28 . H281 . 119.6 no C29 . C28 . H281 . 119.1 no C20 . C29 . C28 . 120.2(5) yes C20 . C29 . H291 . 120.1 no C28 . C29 . H291 . 119.7 no C14 . C15 . C16 . 118.5(4) yes C14 . C15 . H301 . 121.5 no C16 . C15 . H301 . 120.1 no C15 . C16 . C17 . 121.3(5) yes C15 . C16 . H311 . 118.9 no C17 . C16 . H311 . 119.8 no C16 . C17 . C18 . 120.8(5) yes C16 . C17 . H321 . 119.9 no C18 . C17 . H321 . 119.4 no C17 . C18 . C19 . 117.7(5) yes C17 . C18 . H331 . 121.3 no C19 . C18 . H331 . 121.0 no _iucr_refine_instruction_details_constraints ; # # Punched on 17/01/13 at 22:14:45 # #LIST 12 BLOCK SCALE X'S, U'S RIDE C ( 2,X'S) H ( 1,X'S) RIDE C ( 3,X'S) H ( 2,X'S) RIDE C ( 4,X'S) H ( 3,X'S) RIDE C ( 5,X'S) H ( 4,X'S) RIDE C ( 6,X'S) H ( 5,X'S) RIDE C ( 12,X'S) H ( 10,X'S) RIDE C ( 11,X'S) H ( 9,X'S) RIDE C ( 10,X'S) H ( 8,X'S) RIDE C ( 9,X'S) H ( 7,X'S) RIDE C ( 8,X'S) H ( 6,X'S) RIDE C ( 26,X'S) H ( 241,X'S) RIDE C ( 25,X'S) H ( 251,X'S) RIDE C ( 24,X'S) H ( 261,X'S) RIDE C ( 23,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 ( 15,X'S) H ( 301,X'S) RIDE C ( 16,X'S) H ( 311,X'S) RIDE C ( 17,X'S) H ( 321,X'S) RIDE C ( 18,X'S) H ( 331,X'S) END ; _iucr_refine_instruction_details_restraints ; # # Punched on 17/01/13 at 22:14:45 # #LIST 16 NO REM HREST START (DO NOT REMOVE THIS LINE) REM HREST END (DO NOT REMOVE THIS LINE) END ; # Manually omitted reflections loop_ _oxford_refln_omitted_index_h _oxford_refln_omitted_index_k _oxford_refln_omitted_index_l _oxford_refln_omitted_flag _oxford_refln_omitted_details 9 9 12 x . 24 6 12 x . 22 0 10 x . 26 4 14 x . _database_code_depnum_ccdc_archive 'CCDC 949538' ####################################################################### # # 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_4 #==================================================================== #data_New_Global_Publ_Block # start Validation Reply Form _vrf_SHFSU01_I ; PROBLEM: The absolute value of parameter shift to su ratio > 0.20 RESPONSE: The only available crystal was of poor quality. ; _vrf_PLAT080_I ; PROBLEM: Maximum Shift/Error ............................ 0.44 RESPONSE: The only available crystal was of poor quality. ; # end Validation Reply Form #==================================================================== #data_global _audit_creation_date 13-01-18 _audit_creation_method CRYSTALS_ver_14.40 _oxford_structure_analysis_title 'P-1 in P-1' _chemical_name_systematic ? _chemical_melting_point ? # Hand-made tables can be put in the cif. The number of columns # is set in the loop header. # The contants of each column can either be a piece of text # without any spaces (eg a number) or other text enclosed in " " # Remove the leading # in the following example #geom_extra_table_head_A #; #Table 2. #Molecular parameters deviating most from MOGUL averages #; # #loop_ #_geom_extra_tableA_col_1 #_geom_extra_tableA_col_2 #_geom_extra_tableA_col_3 #_geom_extra_tableA_col_4 # #Parameter "Observed Value" "MOGUL Value" "MOGUL e.s.d" #N5-C6-C4 129 124 "7 (\%)" #C3-O10-C2 105 109 "2 (\%)" #C6-O7 1.25 1.22 ".02 (\%A)" # #data_1 _exptl_special_details ; The crystal was placed in the cold stream of an Oxford Cryosystems open-flow nitrogen cryostat (Cosier & Glazer, 1986) with a nominal stability of 0.1K. Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105-107. ; _refine_special_details ; ? ; #--------------------------------------------------------------- # _oxford_ data items, April 2010: # There is some uncertainty about the correct way of forming local data # names, e.g. # _atom_site_special_shape_oxford # or # _oxford_atom_site_special_shape # see: # http://www.iucr.org/resources/cif/spec/version1.1/semantics#namespace # A reserved prefix, e.g. foo, must be used in the following way # " If the data file contains items defined in a DDL1 dictionary, the # local data names assigned under the reserved prefix must contain it as # their first component, e.g. _foo_atom_site_my_item. " # However, this seems to say the opposite: # http://www.iucr.org/__data/iucr/cif/standard/cifstd8.html # According to advice from the IUCr, CRYSTALS is correct #--------------------------------------------------------------- # End of 'script/refcif.dat' #end of refcif _cell_length_a 8.9390(18) _cell_length_b 10.462(2) _cell_length_c 12.493(3) _cell_angle_alpha 99.64(3) _cell_angle_beta 97.01(3) _cell_angle_gamma 106.24(3) _cell_volume 1088.2(5) _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1 ' _symmetry_space_group_name_Hall ? 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' B 0.0013 0.0007 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 0.0061 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' 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 = C30 H20 B1 N1 O2 # Dc = 1.33 Fooo = 444.00 Mu = 0.82 M = 437.31 # Found Formula = C29 H20 B1 N1 O2 # Dc = 1.30 FOOO = 444.00 Mu = 0.80 M = 425.29 _chemical_formula_sum 'C29 H20 B1 N1 O2' _chemical_formula_moiety 'C29 H20 B1 N1 O2' _chemical_compound_source ? _chemical_formula_weight 425.29 _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _cell_measurement_temperature 293 _exptl_crystal_description ? _exptl_crystal_colour ? _exptl_crystal_size_min ? _exptl_crystal_size_mid ? _exptl_crystal_size_max ? _exptl_crystal_density_diffrn 1.298 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 444 _exptl_absorpt_coefficient_mu 0.080 # Sheldrick geometric approximatio 1.00 1.00 _exptl_absorpt_correction_type none _diffrn_measurement_device_type Unknown _diffrn_measurement_device Serial _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _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 'SHELXS 86 (Sheldrick, 1986)' _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 293 _diffrn_reflns_number 5013 _reflns_number_total 5013 _diffrn_reflns_av_R_equivalents 0.000 # Number of reflections without Friedels Law is 0 # Number of reflections with Friedels Law is 5013 # Theoretical number of reflections is about 10013 _diffrn_reflns_theta_min 2.656 _diffrn_reflns_theta_max 27.513 _diffrn_measured_fraction_theta_max 0.998 _diffrn_reflns_theta_full 27.513 _diffrn_measured_fraction_theta_full 0.998 _diffrn_reflns_limit_h_min -11 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_limit_l_max 16 _reflns_limit_h_min -11 _reflns_limit_h_max 11 _reflns_limit_k_min -13 _reflns_limit_k_max 13 _reflns_limit_l_min 0 _reflns_limit_l_max 16 _oxford_diffrn_Wilson_B_factor 3.57 _oxford_diffrn_Wilson_scale 4.93 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_diff_density_min -0.34 _refine_diff_density_max 0.42 # 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>0.0\s(I) _refine_ls_number_reflns 5001 _refine_ls_number_restraints 0 _refine_ls_number_parameters 299 _oxford_refine_ls_R_factor_ref 0.0753 _refine_ls_wR_factor_ref 0.1233 _refine_ls_goodness_of_fit_ref 1.0068 _refine_ls_shift/su_max 0.0003051 _refine_ls_shift/su_mean 0.0000272 # The values computed with all filters except I/sigma _oxford_reflns_number_all 5002 _refine_ls_R_factor_all 0.0754 _refine_ls_wR_factor_all 0.1234 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 3368 _refine_ls_R_factor_gt 0.0469 _refine_ls_wR_factor_gt 0.1026 # 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, 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: 5.54 7.28 2.04 ; # 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 C1 C 0.1911(2) 0.76313(17) 0.76517(12) 0.0405 1.0000 Uani . . . . . . C2 C 0.2530(2) 0.88257(18) 0.72768(15) 0.0490 1.0000 Uani . . . . . . C3 C 0.1714(3) 0.9769(2) 0.72084(18) 0.0615 1.0000 Uani . . . . . . C4 C 0.0264(3) 0.9554(3) 0.75171(19) 0.0708 1.0000 Uani . . . . . . C5 C -0.0378(3) 0.8397(3) 0.7895(2) 0.0702 1.0000 Uani . . . . . . C6 C 0.0434(2) 0.7452(2) 0.79588(16) 0.0541 1.0000 Uani . . . . . . C7 C 0.44691(19) 0.69636(17) 0.85635(13) 0.0397 1.0000 Uani . . . . . . C8 C 0.5243(2) 0.82935(19) 0.91404(16) 0.0503 1.0000 Uani . . . . . . C9 C 0.6652(3) 0.8637(2) 0.98843(18) 0.0608 1.0000 Uani . . . . . . C10 C 0.7314(3) 0.7644(3) 1.00811(19) 0.0661 1.0000 Uani . . . . . . C11 C 0.6573(3) 0.6313(2) 0.95334(19) 0.0648 1.0000 Uani . . . . . . C12 C 0.5179(2) 0.5982(2) 0.87869(16) 0.0509 1.0000 Uani . . . . . . C13 C 0.2051(2) 0.49612(17) 0.57858(13) 0.0404 1.0000 Uani . . . . . . C14 C 0.4220(2) 0.65917(18) 0.58366(14) 0.0429 1.0000 Uani . . . . . . C15 C 0.5600(2) 0.7673(2) 0.60904(17) 0.0524 1.0000 Uani . . . . . . C16 C 0.6397(3) 0.7934(2) 0.5228(2) 0.0631 1.0000 Uani . . . . . . C17 C 0.5837(3) 0.7156(2) 0.41620(19) 0.0636 1.0000 Uani . . . . . . C18 C 0.4468(3) 0.6075(2) 0.39040(16) 0.0564 1.0000 Uani . . . . . . C19 C 0.3699(2) 0.58237(18) 0.47699(15) 0.0459 1.0000 Uani . . . . . . C20 C 0.0761(2) 0.40563(16) 0.60970(13) 0.0403 1.0000 Uani . . . . . . C21 C 0.0685(2) 0.42701(16) 0.72195(13) 0.0389 1.0000 Uani . . . . . . C22 C -0.0582(2) 0.33892(16) 0.75904(14) 0.0415 1.0000 Uani . . . . . . C23 C -0.0738(2) 0.3595(2) 0.87125(16) 0.0535 1.0000 Uani . . . . . . C24 C -0.2010(3) 0.2799(2) 0.90453(19) 0.0664 1.0000 Uani . . . . . . C25 C -0.3170(3) 0.1759(2) 0.8270(2) 0.0672 1.0000 Uani . . . . . . C26 C -0.3023(3) 0.1517(2) 0.71883(19) 0.0580 1.0000 Uani . . . . . . C27 C -0.1737(2) 0.23189(16) 0.68092(15) 0.0447 1.0000 Uani . . . . . . C28 C -0.1574(2) 0.21102(18) 0.56794(16) 0.0509 1.0000 Uani . . . . . . C29 C -0.0373(2) 0.29389(18) 0.53292(14) 0.0473 1.0000 Uani . . . . . . O1 O 0.17730(14) 0.52474(11) 0.79640(9) 0.0434 1.0000 Uani . . . . . . O2 O 0.23349(16) 0.47858(12) 0.47453(9) 0.0464 1.0000 Uani . . . . . . N1 N 0.31124(17) 0.60175(14) 0.64639(11) 0.0396 1.0000 Uani . . . . . . B1 B 0.2831(2) 0.65146(19) 0.77096(14) 0.0388 1.0000 Uani . . . . . . H21 H 0.3550 0.9004 0.7075 0.0583 1.0000 Uiso R . . . . . H31 H 0.2168 1.0564 0.6957 0.0742 1.0000 Uiso R . . . . . H41 H -0.0291 1.0191 0.7470 0.0856 1.0000 Uiso R . . . . . H51 H -0.1381 0.8230 0.8107 0.0840 1.0000 Uiso R . . . . . H61 H -0.0019 0.6666 0.8219 0.0652 1.0000 Uiso R . . . . . H81 H 0.4767 0.8977 0.9027 0.0619 1.0000 Uiso R . . . . . H91 H 0.7157 0.9560 1.0255 0.0738 1.0000 Uiso R . . . . . H101 H 0.8288 0.7879 1.0584 0.0793 1.0000 Uiso R . . . . . H111 H 0.7023 0.5611 0.9663 0.0781 1.0000 Uiso R . . . . . H121 H 0.4669 0.5058 0.8430 0.0610 1.0000 Uiso R . . . . . H151 H 0.5966 0.8186 0.6812 0.0622 1.0000 Uiso R . . . . . H161 H 0.7354 0.8634 0.5377 0.0760 1.0000 Uiso R . . . . . H171 H 0.6411 0.7358 0.3601 0.0751 1.0000 Uiso R . . . . . H181 H 0.4079 0.5537 0.3197 0.0674 1.0000 Uiso R . . . . . H231 H 0.0078 0.4300 0.9225 0.0639 1.0000 Uiso R . . . . . H241 H -0.2107 0.2961 0.9792 0.0796 1.0000 Uiso R . . . . . H251 H -0.4067 0.1239 0.8520 0.0806 1.0000 Uiso R . . . . . H261 H -0.3808 0.0814 0.6670 0.0703 1.0000 Uiso R . . . . . H281 H -0.2356 0.1381 0.5174 0.0612 1.0000 Uiso R . . . . . H291 H -0.0246 0.2801 0.4586 0.0569 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 C1 0.0454(8) 0.0430(8) 0.0283(7) -0.0004(6) 0.0018(6) 0.0126(7) C2 0.0564(10) 0.0425(9) 0.0439(9) 0.0023(7) 0.0073(8) 0.0133(8) C3 0.0826(15) 0.0462(10) 0.0556(12) 0.0082(8) 0.0048(10) 0.0242(10) C4 0.0834(16) 0.0752(15) 0.0636(13) 0.0078(11) 0.0015(12) 0.0487(13) C5 0.0603(13) 0.0919(17) 0.0712(14) 0.0173(13) 0.0169(11) 0.0416(13) C6 0.0529(10) 0.0633(12) 0.0500(10) 0.0131(9) 0.0111(8) 0.0226(9) C7 0.0420(8) 0.0436(8) 0.0323(7) 0.0063(6) 0.0097(6) 0.0109(7) C8 0.0492(10) 0.0458(9) 0.0500(10) 0.0005(8) 0.0010(8) 0.0139(8) C9 0.0544(11) 0.0578(12) 0.0565(11) -0.0059(9) -0.0024(9) 0.0112(9) C10 0.0511(11) 0.0816(15) 0.0583(12) 0.0052(11) -0.0065(9) 0.0211(11) C11 0.0649(13) 0.0715(14) 0.0640(13) 0.0175(11) 0.0006(10) 0.0331(11) C12 0.0582(11) 0.0479(10) 0.0478(10) 0.0093(8) 0.0080(8) 0.0193(8) C13 0.0513(9) 0.0415(8) 0.0306(7) 0.0039(6) 0.0076(7) 0.0197(7) C14 0.0513(9) 0.0436(9) 0.0416(9) 0.0115(7) 0.0156(7) 0.0223(7) C15 0.0538(10) 0.0497(10) 0.0573(11) 0.0136(8) 0.0180(9) 0.0166(8) C16 0.0630(13) 0.0588(12) 0.0785(15) 0.0244(11) 0.0301(11) 0.0229(10) C17 0.0762(14) 0.0724(14) 0.0655(13) 0.0334(11) 0.0393(11) 0.0375(12) C18 0.0770(14) 0.0628(12) 0.0464(10) 0.0177(9) 0.0267(9) 0.0383(11) C19 0.0575(10) 0.0465(9) 0.0431(9) 0.0128(7) 0.0151(8) 0.0265(8) C20 0.0467(9) 0.0361(8) 0.0358(8) 0.0024(6) 0.0037(7) 0.0137(7) C21 0.0447(8) 0.0347(8) 0.0355(8) 0.0037(6) 0.0037(6) 0.0132(7) C22 0.0473(9) 0.0363(8) 0.0400(8) 0.0072(6) 0.0048(7) 0.0132(7) C23 0.0597(11) 0.0504(10) 0.0437(10) 0.0090(8) 0.0097(8) 0.0068(9) C24 0.0727(14) 0.0666(13) 0.0537(12) 0.0176(10) 0.0190(10) 0.0056(11) C25 0.0650(13) 0.0584(12) 0.0722(15) 0.0241(11) 0.0161(11) 0.0019(10) C26 0.0573(11) 0.0422(10) 0.0659(13) 0.0139(9) 0.0046(9) 0.0029(8) C27 0.0485(9) 0.0339(8) 0.0492(9) 0.0081(7) 0.0017(7) 0.0118(7) C28 0.0548(10) 0.0398(9) 0.0480(10) 0.0004(7) -0.0026(8) 0.0087(8) C29 0.0570(10) 0.0438(9) 0.0354(8) -0.0013(7) 0.0019(7) 0.0146(8) O1 0.0503(7) 0.0405(6) 0.0316(5) 0.0039(4) 0.0055(5) 0.0042(5) O2 0.0607(8) 0.0488(7) 0.0316(6) 0.0037(5) 0.0112(5) 0.0213(6) N1 0.0470(7) 0.0386(7) 0.0336(7) 0.0047(5) 0.0098(6) 0.0144(6) B1 0.0447(9) 0.0367(9) 0.0307(8) 0.0015(6) 0.0063(7) 0.0092(7) _refine_ls_extinction_coef 278(11) _refine_ls_extinction_method 'Larson (1970), Equation 22' _oxford_refine_ls_scale 0.4934(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 C1 . C2 . 1.400(3) yes C1 . C6 . 1.390(3) yes C1 . B1 . 1.612(2) yes C2 . C3 . 1.389(3) yes C2 . H21 . 0.952 no C3 . C4 . 1.366(3) yes C3 . H31 . 0.942 no C4 . C5 . 1.373(4) yes C4 . H41 . 0.941 no C5 . C6 . 1.388(3) yes C5 . H51 . 0.944 no C6 . H61 . 0.939 no C7 . C8 . 1.392(2) yes C7 . C12 . 1.397(2) yes C7 . B1 . 1.603(3) yes C8 . C9 . 1.389(3) yes C8 . H81 . 0.950 no C9 . C10 . 1.373(3) yes C9 . H91 . 0.951 no C10 . C11 . 1.379(3) yes C10 . H101 . 0.953 no C11 . C12 . 1.382(3) yes C11 . H111 . 0.957 no C12 . H121 . 0.949 no C13 . C20 . 1.414(2) yes C13 . O2 . 1.3470(19) yes C13 . N1 . 1.320(2) yes C14 . C15 . 1.381(3) yes C14 . C19 . 1.385(3) yes C14 . N1 . 1.403(2) yes C15 . C16 . 1.385(3) yes C15 . H151 . 0.936 no C16 . C17 . 1.391(3) yes C16 . H161 . 0.932 no C17 . C18 . 1.374(3) yes C17 . H171 . 0.936 no C18 . C19 . 1.374(3) yes C18 . H181 . 0.931 no C19 . O2 . 1.380(2) yes C20 . C21 . 1.396(2) yes C20 . C29 . 1.428(2) yes C21 . C22 . 1.427(2) yes C21 . O1 . 1.327(2) yes C22 . C23 . 1.412(2) yes C22 . C27 . 1.419(2) yes C23 . C24 . 1.364(3) yes C23 . H231 . 0.956 no C24 . C25 . 1.403(3) yes C24 . H241 . 0.939 no C25 . C26 . 1.363(3) yes C25 . H251 . 0.954 no C26 . C27 . 1.406(3) yes C26 . H261 . 0.945 no C27 . C28 . 1.423(3) yes C28 . C29 . 1.348(3) yes C28 . H281 . 0.949 no C29 . H291 . 0.941 no O1 . B1 . 1.505(2) yes N1 . B1 . 1.629(2) yes 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 . C1 . C6 . 115.92(17) yes C2 . C1 . B1 . 122.44(16) yes C6 . C1 . B1 . 121.64(16) yes C1 . C2 . C3 . 122.02(19) yes C1 . C2 . H21 . 118.9 no C3 . C2 . H21 . 119.1 no C2 . C3 . C4 . 120.3(2) yes C2 . C3 . H31 . 119.8 no C4 . C3 . H31 . 120.0 no C3 . C4 . C5 . 119.4(2) yes C3 . C4 . H41 . 120.3 no C5 . C4 . H41 . 120.3 no C4 . C5 . C6 . 120.4(2) yes C4 . C5 . H51 . 120.5 no C6 . C5 . H51 . 119.2 no C1 . C6 . C5 . 122.0(2) yes C1 . C6 . H61 . 118.5 no C5 . C6 . H61 . 119.4 no C8 . C7 . C12 . 116.17(16) yes C8 . C7 . B1 . 124.08(15) yes C12 . C7 . B1 . 119.72(15) yes C7 . C8 . C9 . 122.27(18) yes C7 . C8 . H81 . 118.1 no C9 . C8 . H81 . 119.6 no C8 . C9 . C10 . 119.8(2) yes C8 . C9 . H91 . 119.9 no C10 . C9 . H91 . 120.2 no C9 . C10 . C11 . 119.53(19) yes C9 . C10 . H101 . 120.0 no C11 . C10 . H101 . 120.5 no C10 . C11 . C12 . 120.2(2) yes C10 . C11 . H111 . 120.3 no C12 . C11 . H111 . 119.4 no C7 . C12 . C11 . 121.95(19) yes C7 . C12 . H121 . 118.8 no C11 . C12 . H121 . 119.3 no C20 . C13 . O2 . 121.85(15) yes C20 . C13 . N1 . 124.85(15) yes O2 . C13 . N1 . 113.27(16) yes C15 . C14 . C19 . 120.39(17) yes C15 . C14 . N1 . 133.27(17) yes C19 . C14 . N1 . 106.33(16) yes C14 . C15 . C16 . 116.4(2) yes C14 . C15 . H151 . 120.8 no C16 . C15 . H151 . 122.8 no C15 . C16 . C17 . 122.0(2) yes C15 . C16 . H161 . 118.6 no C17 . C16 . H161 . 119.4 no C16 . C17 . C18 . 121.94(19) yes C16 . C17 . H171 . 119.6 no C18 . C17 . H171 . 118.4 no C17 . C18 . C19 . 115.3(2) yes C17 . C18 . H181 . 123.2 no C19 . C18 . H181 . 121.5 no C14 . C19 . C18 . 123.94(19) yes C14 . C19 . O2 . 108.89(15) yes C18 . C19 . O2 . 127.16(18) yes C13 . C20 . C21 . 116.27(15) yes C13 . C20 . C29 . 122.83(16) yes C21 . C20 . C29 . 120.84(16) yes C20 . C21 . C22 . 119.16(15) yes C20 . C21 . O1 . 122.41(16) yes C22 . C21 . O1 . 118.40(15) yes C21 . C22 . C23 . 121.16(16) yes C21 . C22 . C27 . 119.21(16) yes C23 . C22 . C27 . 119.59(17) yes C22 . C23 . C24 . 120.58(19) yes C22 . C23 . H231 . 117.8 no C24 . C23 . H231 . 121.6 no C23 . C24 . C25 . 119.9(2) yes C23 . C24 . H241 . 119.5 no C25 . C24 . H241 . 120.5 no C24 . C25 . C26 . 120.5(2) yes C24 . C25 . H251 . 118.2 no C26 . C25 . H251 . 121.2 no C25 . C26 . C27 . 121.4(2) yes C25 . C26 . H261 . 120.1 no C27 . C26 . H261 . 118.5 no C22 . C27 . C26 . 117.98(18) yes C22 . C27 . C28 . 119.49(17) yes C26 . C27 . C28 . 122.52(17) yes C27 . C28 . C29 . 121.28(16) yes C27 . C28 . H281 . 117.9 no C29 . C28 . H281 . 120.8 no C20 . C29 . C28 . 119.92(17) yes C20 . C29 . H291 . 118.2 no C28 . C29 . H291 . 121.9 no C21 . O1 . B1 . 124.33(13) yes C19 . O2 . C13 . 105.12(14) yes C14 . N1 . C13 . 106.36(14) yes C14 . N1 . B1 . 132.98(14) yes C13 . N1 . B1 . 120.09(14) yes N1 . B1 . C1 . 106.82(13) yes N1 . B1 . C7 . 110.04(14) yes C1 . B1 . C7 . 117.33(13) yes N1 . B1 . O1 . 104.03(13) yes C1 . B1 . O1 . 110.39(14) yes C7 . B1 . O1 . 107.44(14) yes _iucr_refine_instruction_details_constraints ; # # Punched on 11/03/13 at 17:03:13 # #LIST 12 BLOCK SCALE X'S, U'S CONT EXTPARAM RIDE C ( 2,X'S) H ( 21,X'S) RIDE C ( 3,X'S) H ( 31,X'S) RIDE C ( 4,X'S) H ( 41,X'S) RIDE C ( 5,X'S) H ( 51,X'S) RIDE C ( 6,X'S) H ( 61,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 ( 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 ( 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 ( 28,X'S) H ( 281,X'S) RIDE C ( 29,X'S) H ( 291,X'S) END ; _iucr_refine_instruction_details_restraints ; # # Punched on 11/03/13 at 17:03:13 # #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 949539' ####################################################################### # # 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_5 #data_global _audit_creation_date 13-01-18 _audit_creation_method CRYSTALS_ver_14.40 _oxford_structure_analysis_title 'Pbca in Pbca' _chemical_name_systematic ? _chemical_melting_point ? # Hand-made tables can be put in the cif. The number of columns # is set in the loop header. # The contants of each column can either be a piece of text # without any spaces (eg a number) or other text enclosed in " " # Remove the leading # in the following example #geom_extra_table_head_A #; #Table 2. #Molecular parameters deviating most from MOGUL averages #; # #loop_ #_geom_extra_tableA_col_1 #_geom_extra_tableA_col_2 #_geom_extra_tableA_col_3 #_geom_extra_tableA_col_4 # #Parameter "Observed Value" "MOGUL Value" "MOGUL e.s.d" #N5-C6-C4 129 124 "7 (\%)" #C3-O10-C2 105 109 "2 (\%)" #C6-O7 1.25 1.22 ".02 (\%A)" # #data_1 _exptl_special_details ; The crystal was placed in the cold stream of an Oxford Cryosystems open-flow nitrogen cryostat (Cosier & Glazer, 1986) with a nominal stability of 0.1K. Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105-107. ; _refine_special_details ; ? ; #--------------------------------------------------------------- # _oxford_ data items, April 2010: # There is some uncertainty about the correct way of forming local data # names, e.g. # _atom_site_special_shape_oxford # or # _oxford_atom_site_special_shape # see: # http://www.iucr.org/resources/cif/spec/version1.1/semantics#namespace # A reserved prefix, e.g. foo, must be used in the following way # " If the data file contains items defined in a DDL1 dictionary, the # local data names assigned under the reserved prefix must contain it as # their first component, e.g. _foo_atom_site_my_item. " # However, this seems to say the opposite: # http://www.iucr.org/__data/iucr/cif/standard/cifstd8.html # According to advice from the IUCr, CRYSTALS is correct #--------------------------------------------------------------- # End of 'script/refcif.dat' #end of refcif _cell_length_a 12.122(2) _cell_length_b 16.401(3) _cell_length_c 21.944(4) _cell_angle_alpha 90 _cell_angle_beta 90 _cell_angle_gamma 90 _cell_volume 4362.8(15) _symmetry_cell_setting orthorhombic _symmetry_space_group_name_H-M 'P b c a ' _symmetry_space_group_name_Hall '-P 2ac 2ab' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z -x+1/2,y+1/2,z x+1/2,-y+1/2,-z x,-y+1/2,z+1/2 -x,y+1/2,-z+1/2 -x+1/2,-y,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 0.0033 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' B 0.0013 0.0007 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 0.0061 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' 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 = C29 H20 B1 N1 O2 # Dc = 1.29 Fooo = 1776.00 Mu = 0.80 M = 425.29 # Found Formula = C29 H20 B1 N1 O2 # Dc = 1.29 FOOO = 1776.00 Mu = 0.80 M = 425.29 _chemical_formula_sum 'C29 H20 B1 N1 O2' _chemical_formula_moiety 'C29 H20 B1 N1 O2' _chemical_compound_source ? _chemical_formula_weight 425.29 _cell_measurement_reflns_used 25 _cell_measurement_theta_min 15 _cell_measurement_theta_max 18 _cell_measurement_temperature 298 _exptl_crystal_description needle _exptl_crystal_colour yellow _exptl_crystal_size_min 0.150 _exptl_crystal_size_mid 0.220 _exptl_crystal_size_max 0.250 _exptl_crystal_density_diffrn 1.295 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 1776 _exptl_absorpt_coefficient_mu 0.080 # Sheldrick geometric approximatio 0.98 0.99 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_process_details '(North et al., 1968)' _exptl_absorpt_correction_T_min 0.93 _exptl_absorpt_correction_T_max 0.99 _diffrn_measurement_device_type Unknown _diffrn_measurement_device Serial _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _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 150 _diffrn_standards_number 3 _diffrn_standards_decay_% 0.00 _diffrn_ambient_temperature 298 _diffrn_reflns_number 5571 _reflns_number_total 5013 _diffrn_reflns_av_R_equivalents 0.000 # Number of reflections without Friedels Law is 5013 # Number of reflections with Friedels Law is 0 # Theoretical number of reflections is about 5009 _diffrn_reflns_theta_min 2.504 _diffrn_reflns_theta_max 27.495 _diffrn_measured_fraction_theta_max 0.999 _diffrn_reflns_theta_full 27.495 _diffrn_measured_fraction_theta_full 0.999 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 28 _reflns_limit_h_min 0 _reflns_limit_h_max 15 _reflns_limit_k_min 0 _reflns_limit_k_max 21 _reflns_limit_l_min 0 _reflns_limit_l_max 28 _oxford_diffrn_Wilson_B_factor 2.50 _oxford_diffrn_Wilson_scale 107.26 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_diff_density_min -1.07 _refine_diff_density_max 0.96 # 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>-10.0\s(I) _refine_ls_number_reflns 4999 _refine_ls_number_restraints 0 _refine_ls_number_parameters 298 _oxford_refine_ls_R_factor_ref 0.2391 _refine_ls_wR_factor_ref 0.1645 _refine_ls_goodness_of_fit_ref 1.0927 _refine_ls_shift/su_max 0.0001350 _refine_ls_shift/su_mean 0.0000285 # The values computed with all filters except I/sigma _oxford_reflns_number_all 4999 _refine_ls_R_factor_all 0.2391 _refine_ls_wR_factor_all 0.1645 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 1610 _refine_ls_R_factor_gt 0.0638 _refine_ls_wR_factor_gt 0.0840 # 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, 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: 2.77 2.86 0.689 ; # 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 O2 O 0.2712(3) 0.6585(2) 0.78204(16) 0.0505 1.0000 Uani . . . . . . C13 C 0.2780(5) 0.6711(4) 0.7213(3) 0.0484 1.0000 Uani . . . . . . N1 N 0.1995(4) 0.6353(3) 0.6904(2) 0.0469 1.0000 Uani . . . . . . C14 C 0.1323(5) 0.5957(4) 0.7331(2) 0.0472 1.0000 Uani . . . . . . C19 C 0.1773(5) 0.6107(4) 0.7897(3) 0.0513 1.0000 Uani . . . . . . C18 C 0.1324(5) 0.5854(4) 0.8434(3) 0.0594 1.0000 Uani . . . . . . C17 C 0.0357(5) 0.5407(4) 0.8384(3) 0.0647 1.0000 Uani . . . . . . C16 C -0.0093(5) 0.5226(4) 0.7821(3) 0.0598 1.0000 Uani . . . . . . C15 C 0.0370(5) 0.5497(4) 0.7278(3) 0.0568 1.0000 Uani . . . . . . B1 B 0.1947(6) 0.6420(4) 0.6161(3) 0.0481 1.0000 Uani . . . . . . O1 O 0.2572(3) 0.7184(2) 0.60253(17) 0.0548 1.0000 Uani . . . . . . C21 C 0.3500(5) 0.7403(4) 0.6325(3) 0.0513 1.0000 Uani . . . . . . C20 C 0.3636(5) 0.7207(3) 0.6954(2) 0.0472 1.0000 Uani . . . . . . C29 C 0.4523(4) 0.7497(3) 0.7277(3) 0.0511 1.0000 Uani . . . . . . C28 C 0.5325(5) 0.7986(3) 0.6995(3) 0.0514 1.0000 Uani . . . . . . C23 C 0.5208(5) 0.8160(4) 0.6364(3) 0.0564 1.0000 Uani . . . . . . C22 C 0.4287(5) 0.7865(4) 0.6039(3) 0.0585 1.0000 Uani . . . . . . C24 C 0.6025(5) 0.8651(4) 0.6082(3) 0.0704 1.0000 Uani . . . . . . C25 C 0.6903(6) 0.8942(4) 0.6401(3) 0.0733 1.0000 Uani . . . . . . C26 C 0.7015(5) 0.8766(4) 0.7020(3) 0.0703 1.0000 Uani . . . . . . C27 C 0.6255(5) 0.8300(4) 0.7313(3) 0.0624 1.0000 Uani . . . . . . C1 C 0.2558(5) 0.5640(4) 0.5880(2) 0.0502 1.0000 Uani . . . . . . C2 C 0.2518(5) 0.4864(4) 0.6125(3) 0.0592 1.0000 Uani . . . . . . C3 C 0.3025(5) 0.4199(4) 0.5847(4) 0.0748 1.0000 Uani . . . . . . C4 C 0.3593(6) 0.4317(5) 0.5307(4) 0.0806 1.0000 Uani . . . . . . C5 C 0.3626(6) 0.5088(5) 0.5054(3) 0.0760 1.0000 Uani . . . . . . C6 C 0.3117(5) 0.5738(4) 0.5331(3) 0.0640 1.0000 Uani . . . . . . C7 C 0.0697(5) 0.6551(4) 0.5950(3) 0.0503 1.0000 Uani . . . . . . C8 C 0.0067(5) 0.5931(4) 0.5681(3) 0.0599 1.0000 Uani . . . . . . C9 C -0.1014(6) 0.6059(5) 0.5500(3) 0.0710 1.0000 Uani . . . . . . C10 C -0.1500(6) 0.6809(5) 0.5577(3) 0.0740 1.0000 Uani . . . . . . C11 C -0.0909(6) 0.7426(5) 0.5845(3) 0.0716 1.0000 Uani . . . . . . C12 C 0.0183(5) 0.7300(4) 0.6029(3) 0.0596 1.0000 Uani . . . . . . H14 H 0.1620 0.5965 0.8839 0.0814 1.0000 Uiso R . . . . . H13 H -0.0034 0.5225 0.8752 0.0869 1.0000 Uiso R . . . . . H12 H -0.0793 0.4906 0.7805 0.0795 1.0000 Uiso R . . . . . H11 H 0.0076 0.5387 0.6891 0.0781 1.0000 Uiso R . . . . . H20 H 0.4588 0.7371 0.7709 0.0718 1.0000 Uiso R . . . . . H15 H 0.4218 0.7962 0.5610 0.0856 1.0000 Uiso R . . . . . H16 H 0.5986 0.8775 0.5654 0.0950 1.0000 Uiso R . . . . . H17 H 0.7464 0.9274 0.6203 0.0968 1.0000 Uiso R . . . . . H18 H 0.7673 0.8962 0.7231 0.0904 1.0000 Uiso R . . . . . H19 H 0.6328 0.8193 0.7748 0.0860 1.0000 Uiso R . . . . . H1 H 0.2104 0.4756 0.6524 0.0789 1.0000 Uiso R . . . . . H2 H 0.2991 0.3673 0.6037 0.0960 1.0000 Uiso R . . . . . H3 H 0.3958 0.3885 0.5128 0.1042 1.0000 Uiso R . . . . . H4 H 0.3997 0.5176 0.4675 0.1014 1.0000 Uiso R . . . . . H5 H 0.3129 0.6291 0.5153 0.0911 1.0000 Uiso R . . . . . H6 H 0.0410 0.5397 0.5609 0.0867 1.0000 Uiso R . . . . . H7 H -0.1438 0.5634 0.5335 0.0938 1.0000 Uiso R . . . . . H8 H -0.2284 0.6889 0.5447 0.0960 1.0000 Uiso R . . . . . H9 H -0.1230 0.7972 0.5904 0.0903 1.0000 Uiso R . . . . . H10 H 0.0554 0.7741 0.6207 0.0872 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 O2 0.050(2) 0.062(3) 0.040(2) 0.003(2) -0.0053(19) -0.009(2) C13 0.046(4) 0.052(4) 0.048(3) 0.001(3) -0.003(3) 0.000(3) N1 0.045(3) 0.048(3) 0.048(3) -0.002(2) 0.001(2) -0.003(3) C14 0.044(3) 0.051(4) 0.047(3) -0.001(3) 0.002(3) -0.006(3) C19 0.049(4) 0.055(4) 0.049(4) 0.004(3) -0.003(3) -0.002(3) C18 0.061(4) 0.075(5) 0.043(3) 0.006(3) 0.002(3) -0.004(4) C17 0.060(4) 0.082(5) 0.052(4) 0.015(4) 0.009(3) -0.011(4) C16 0.057(4) 0.062(4) 0.060(4) 0.003(3) 0.002(4) -0.013(3) C15 0.058(4) 0.066(4) 0.047(4) -0.004(3) -0.002(3) 0.000(4) B1 0.049(4) 0.052(4) 0.043(4) 0.009(3) -0.006(3) -0.006(4) O1 0.055(3) 0.055(3) 0.054(2) 0.012(2) -0.008(2) -0.010(2) C21 0.045(3) 0.057(4) 0.051(3) 0.004(3) -0.005(3) -0.003(3) C20 0.043(3) 0.052(4) 0.047(3) 0.000(3) -0.003(3) -0.001(3) C29 0.046(3) 0.051(4) 0.056(4) 0.004(3) -0.004(3) 0.005(3) C28 0.043(3) 0.045(4) 0.066(4) -0.002(3) -0.003(3) -0.004(3) C23 0.049(4) 0.053(4) 0.067(4) 0.005(3) 0.007(3) -0.002(3) C22 0.056(4) 0.066(4) 0.053(4) 0.009(3) -0.003(3) -0.011(4) C24 0.060(4) 0.073(5) 0.078(5) 0.011(4) 0.004(4) -0.013(4) C25 0.057(4) 0.071(5) 0.092(5) 0.008(4) 0.004(4) -0.008(4) C26 0.042(4) 0.073(5) 0.096(6) -0.010(4) -0.003(4) -0.005(4) C27 0.050(4) 0.061(4) 0.077(5) -0.002(4) 0.000(4) 0.005(4) C1 0.043(3) 0.062(4) 0.046(3) 0.000(3) -0.005(3) -0.001(3) C2 0.048(3) 0.060(4) 0.070(4) 0.004(4) 0.002(4) 0.002(3) C3 0.056(4) 0.068(5) 0.100(6) -0.005(5) -0.016(4) -0.003(4) C4 0.058(5) 0.086(6) 0.098(6) -0.035(5) -0.012(5) 0.014(5) C5 0.067(5) 0.105(6) 0.056(4) -0.022(5) -0.001(4) 0.004(5) C6 0.068(4) 0.076(5) 0.048(4) -0.003(4) 0.000(3) 0.003(4) C7 0.053(4) 0.054(4) 0.043(3) 0.002(3) -0.001(3) -0.002(3) C8 0.059(4) 0.068(4) 0.052(4) 0.002(3) -0.012(3) -0.009(4) C9 0.054(4) 0.087(6) 0.072(5) 0.005(4) -0.015(4) -0.014(4) C10 0.051(4) 0.110(6) 0.061(4) 0.009(5) 0.001(4) -0.006(5) C11 0.061(4) 0.080(5) 0.073(5) 0.012(4) 0.001(4) 0.010(4) C12 0.052(4) 0.070(5) 0.058(4) 0.004(4) -0.001(3) -0.004(4) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.12974(6) 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 . C13 . 1.351(6) yes O2 . C19 . 1.393(6) yes C13 . N1 . 1.307(6) yes C13 . C20 . 1.436(7) yes N1 . C14 . 1.402(7) yes N1 . B1 . 1.635(8) yes C14 . C19 . 1.379(7) yes C14 . C15 . 1.384(7) yes C19 . C18 . 1.363(7) yes C18 . C17 . 1.387(8) yes C18 . H14 . 0.975 no C17 . C16 . 1.381(8) yes C17 . H13 . 0.984 no C16 . C15 . 1.389(7) yes C16 . H12 . 0.999 no C15 . H11 . 0.939 no B1 . O1 . 1.494(7) yes B1 . C1 . 1.601(9) yes B1 . C7 . 1.599(8) yes O1 . C21 . 1.352(6) yes C21 . C20 . 1.426(7) yes C21 . C22 . 1.371(7) yes C20 . C29 . 1.373(7) yes C29 . C28 . 1.405(7) yes C29 . H20 . 0.973 no C28 . C23 . 1.422(8) yes C28 . C27 . 1.422(8) yes C23 . C22 . 1.410(8) yes C23 . C24 . 1.419(8) yes C22 . H15 . 0.959 no C24 . C25 . 1.361(8) yes C24 . H16 . 0.961 no C25 . C26 . 1.394(9) yes C25 . H17 . 0.973 no C26 . C27 . 1.359(8) yes C26 . H18 . 0.977 no C27 . H19 . 0.974 no C1 . C2 . 1.382(8) yes C1 . C6 . 1.391(8) yes C2 . C3 . 1.392(9) yes C2 . H1 . 1.024 no C3 . C4 . 1.384(9) yes C3 . H2 . 0.958 no C4 . C5 . 1.382(10) yes C4 . H3 . 0.923 no C5 . C6 . 1.373(9) yes C5 . H4 . 0.957 no C6 . H5 . 0.989 no C7 . C8 . 1.403(8) yes C7 . C12 . 1.388(8) yes C8 . C9 . 1.385(8) yes C8 . H6 . 0.982 no C9 . C10 . 1.375(9) yes C9 . H7 . 0.940 no C10 . C11 . 1.371(9) yes C10 . H8 . 1.001 no C11 . C12 . 1.400(8) yes C11 . H9 . 0.985 no C12 . H10 . 0.937 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 C13 . O2 . C19 . 104.8(4) yes O2 . C13 . N1 . 113.5(5) yes O2 . C13 . C20 . 121.4(5) yes N1 . C13 . C20 . 125.1(5) yes C13 . N1 . C14 . 106.5(4) yes C13 . N1 . B1 . 120.8(5) yes C14 . N1 . B1 . 132.6(5) yes N1 . C14 . C19 . 106.8(5) yes N1 . C14 . C15 . 133.0(5) yes C19 . C14 . C15 . 120.2(5) yes O2 . C19 . C14 . 108.4(5) yes O2 . C19 . C18 . 127.1(5) yes C14 . C19 . C18 . 124.5(6) yes C19 . C18 . C17 . 115.4(6) yes C19 . C18 . H14 . 125.8 no C17 . C18 . H14 . 118.9 no C18 . C17 . C16 . 121.3(6) yes C18 . C17 . H13 . 120.1 no C16 . C17 . H13 . 118.6 no C17 . C16 . C15 . 122.6(6) yes C17 . C16 . H12 . 118.7 no C15 . C16 . H12 . 118.7 no C16 . C15 . C14 . 116.0(5) yes C16 . C15 . H11 . 124.1 no C14 . C15 . H11 . 119.8 no N1 . B1 . O1 . 103.7(5) yes N1 . B1 . C1 . 108.4(5) yes O1 . B1 . C1 . 111.0(5) yes N1 . B1 . C7 . 109.3(5) yes O1 . B1 . C7 . 108.0(5) yes C1 . B1 . C7 . 115.7(5) yes B1 . O1 . C21 . 123.2(5) yes O1 . C21 . C20 . 120.5(5) yes O1 . C21 . C22 . 120.2(5) yes C20 . C21 . C22 . 119.2(6) yes C13 . C20 . C21 . 115.3(5) yes C13 . C20 . C29 . 123.9(5) yes C21 . C20 . C29 . 120.8(6) yes C20 . C29 . C28 . 120.8(5) yes C20 . C29 . H20 . 119.6 no C28 . C29 . H20 . 119.5 no C29 . C28 . C23 . 118.3(6) yes C29 . C28 . C27 . 122.7(6) yes C23 . C28 . C27 . 119.0(6) yes C28 . C23 . C22 . 120.2(6) yes C28 . C23 . C24 . 118.0(6) yes C22 . C23 . C24 . 121.8(6) yes C23 . C22 . C21 . 120.5(6) yes C23 . C22 . H15 . 120.6 no C21 . C22 . H15 . 118.8 no C23 . C24 . C25 . 121.4(7) yes C23 . C24 . H16 . 120.8 no C25 . C24 . H16 . 117.8 no C24 . C25 . C26 . 120.3(7) yes C24 . C25 . H17 . 120.8 no C26 . C25 . H17 . 118.9 no C25 . C26 . C27 . 120.8(7) yes C25 . C26 . H18 . 118.2 no C27 . C26 . H18 . 120.9 no C28 . C27 . C26 . 120.5(6) yes C28 . C27 . H19 . 119.1 no C26 . C27 . H19 . 120.3 no B1 . C1 . C2 . 124.7(5) yes B1 . C1 . C6 . 117.8(6) yes C2 . C1 . C6 . 117.4(6) yes C1 . C2 . C3 . 122.4(6) yes C1 . C2 . H1 . 120.6 no C3 . C2 . H1 . 117.0 no C2 . C3 . C4 . 119.0(7) yes C2 . C3 . H2 . 119.8 no C4 . C3 . H2 . 121.2 no C3 . C4 . C5 . 119.1(7) yes C3 . C4 . H3 . 119.7 no C5 . C4 . H3 . 121.2 no C4 . C5 . C6 . 121.3(7) yes C4 . C5 . H4 . 120.0 no C6 . C5 . H4 . 118.6 no C1 . C6 . C5 . 120.8(7) yes C1 . C6 . H5 . 117.1 no C5 . C6 . H5 . 122.1 no B1 . C7 . C8 . 122.7(6) yes B1 . C7 . C12 . 120.6(6) yes C8 . C7 . C12 . 116.7(6) yes C7 . C8 . C9 . 121.7(7) yes C7 . C8 . H6 . 118.9 no C9 . C8 . H6 . 119.3 no C8 . C9 . C10 . 120.4(7) yes C8 . C9 . H7 . 121.1 no C10 . C9 . H7 . 118.5 no C9 . C10 . C11 . 119.2(7) yes C9 . C10 . H8 . 119.3 no C11 . C10 . H8 . 121.4 no C10 . C11 . C12 . 120.6(7) yes C10 . C11 . H9 . 121.4 no C12 . C11 . H9 . 118.0 no C11 . C12 . C7 . 121.3(7) yes C11 . C12 . H10 . 117.4 no C7 . C12 . H10 . 121.3 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 C3 . H2 . O1 3_545 150.93(19) 0.958 2.536 3.406(9) yes _iucr_refine_instruction_details_constraints ; # # Punched on 18/01/13 at 14:02:15 # #LIST 12 BLOCK SCALE X'S, U'S RIDE C ( 18,X'S) H ( 14,X'S) RIDE C ( 17,X'S) H ( 13,X'S) RIDE C ( 16,X'S) H ( 12,X'S) RIDE C ( 15,X'S) H ( 11,X'S) RIDE C ( 29,X'S) H ( 20,X'S) RIDE C ( 22,X'S) H ( 15,X'S) RIDE C ( 24,X'S) H ( 16,X'S) RIDE C ( 25,X'S) H ( 17,X'S) RIDE C ( 26,X'S) H ( 18,X'S) RIDE C ( 27,X'S) H ( 19,X'S) RIDE C ( 2,X'S) H ( 1,X'S) RIDE C ( 3,X'S) H ( 2,X'S) RIDE C ( 4,X'S) H ( 3,X'S) RIDE C ( 5,X'S) H ( 4,X'S) RIDE C ( 6,X'S) H ( 5,X'S) RIDE C ( 8,X'S) H ( 6,X'S) RIDE C ( 9,X'S) H ( 7,X'S) RIDE C ( 10,X'S) H ( 8,X'S) RIDE C ( 11,X'S) H ( 9,X'S) RIDE C ( 12,X'S) H ( 10,X'S) END ; _iucr_refine_instruction_details_restraints ; # # Punched on 18/01/13 at 14:02:15 # #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 949540' ####################################################################### # # 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_6 #==================================================================== #data_New_Global_Publ_Block # start Validation Reply Form _vrf_PLAT601_I ; PROBLEM: Structure Contains Solvent Accessible VOIDS of . 417 A**3 RESPONSE: severely disordered solvent (C5H10) was squizzed from the structure. ; # end Validation Reply Form #==================================================================== #data_global _audit_creation_date 13-01-18 _audit_creation_method CRYSTALS_ver_14.40 _oxford_structure_analysis_title 'P21n in P2(1)/n' _chemical_name_systematic ? _chemical_melting_point ? # Hand-made tables can be put in the cif. The number of columns # is set in the loop header. # The contants of each column can either be a piece of text # without any spaces (eg a number) or other text enclosed in " " # Remove the leading # in the following example #geom_extra_table_head_A #; #Table 2. #Molecular parameters deviating most from MOGUL averages #; # #loop_ #_geom_extra_tableA_col_1 #_geom_extra_tableA_col_2 #_geom_extra_tableA_col_3 #_geom_extra_tableA_col_4 # #Parameter "Observed Value" "MOGUL Value" "MOGUL e.s.d" #N5-C6-C4 129 124 "7 (\%)" #C3-O10-C2 105 109 "2 (\%)" #C6-O7 1.25 1.22 ".02 (\%A)" # #data_1 _exptl_special_details ; The crystal was placed in the cold stream of an Oxford Cryosystems open-flow nitrogen cryostat (Cosier & Glazer, 1986) with a nominal stability of 0.1K. Cosier, J. & Glazer, A.M., 1986. J. Appl. Cryst. 105-107. ; _refine_special_details ; ? ; #--------------------------------------------------------------- # _oxford_ data items, April 2010: # There is some uncertainty about the correct way of forming local data # names, e.g. # _atom_site_special_shape_oxford # or # _oxford_atom_site_special_shape # see: # http://www.iucr.org/resources/cif/spec/version1.1/semantics#namespace # A reserved prefix, e.g. foo, must be used in the following way # " If the data file contains items defined in a DDL1 dictionary, the # local data names assigned under the reserved prefix must contain it as # their first component, e.g. _foo_atom_site_my_item. " # However, this seems to say the opposite: # http://www.iucr.org/__data/iucr/cif/standard/cifstd8.html # According to advice from the IUCr, CRYSTALS is correct #--------------------------------------------------------------- # End of 'script/refcif.dat' #end of refcif _cell_length_a 8.1950(16) _cell_length_b 19.533(4) _cell_length_c 17.981(4) _cell_angle_alpha 90 _cell_angle_beta 92.27(3) _cell_angle_gamma 90 _cell_volume 2876.0(10) _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 1 21/n 1 ' _symmetry_space_group_name_Hall '-P 2yn' loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,-y,-z -x+1/2,y+1/2,-z+1/2 x+1/2,-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' B 0.0013 0.0007 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 0.0061 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' 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' S 0.1246 0.1234 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' _cell_formula_units_Z 4 # Given Formula = C34 H40 B1 N1 O1 S1 # Dc = 1.20 Fooo = 920.00 Mu = 1.40 M = 521.57 # Found Formula = C29 H20 B1 N1 O1 S1 # Dc = 1.02 FOOO = 920.00 Mu = 1.30 M = 441.36 _chemical_formula_sum 'C29 H20 B1 N1 O1 S1' _chemical_formula_moiety 'C29 H20 B1 N1 O1 S1' _chemical_compound_source ? _chemical_formula_weight 441.36 _cell_measurement_reflns_used 25 _cell_measurement_theta_min 2 _cell_measurement_theta_max 27 _cell_measurement_temperature 298 _exptl_crystal_description needle _exptl_crystal_colour yellow _exptl_crystal_size_min 0.100 _exptl_crystal_size_mid 0.130 _exptl_crystal_size_max 0.220 _exptl_crystal_density_diffrn 1.019 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 920 _exptl_absorpt_coefficient_mu 0.130 # Sheldrick geometric approximatio 0.98 0.99 _exptl_absorpt_correction_type psi-scan _exptl_absorpt_process_details '(North et al., 1968)' _exptl_absorpt_correction_T_min 0.95 _exptl_absorpt_correction_T_max 0.99 _diffrn_measurement_device_type Unknown _diffrn_measurement_device Serial _diffrn_radiation_monochromator graphite _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _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 150 _diffrn_standards_number 25 _diffrn_standards_decay_% 0.00 _diffrn_ambient_temperature 298 _diffrn_reflns_number 6613 _reflns_number_total 6613 _diffrn_reflns_av_R_equivalents 0.056 # Number of reflections without Friedels Law is 6613 # Number of reflections with Friedels Law is 0 # Theoretical number of reflections is about 6633 _diffrn_reflns_theta_min 2.692 _diffrn_reflns_theta_max 27.539 _diffrn_measured_fraction_theta_max 0.996 _diffrn_reflns_theta_full 27.539 _diffrn_measured_fraction_theta_full 0.996 _diffrn_reflns_limit_h_min -10 _diffrn_reflns_limit_h_max 10 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_k_max 25 _diffrn_reflns_limit_l_min 0 _diffrn_reflns_limit_l_max 23 _reflns_limit_h_min -10 _reflns_limit_h_max 10 _reflns_limit_k_min 0 _reflns_limit_k_max 25 _reflns_limit_l_min 0 _reflns_limit_l_max 23 _oxford_diffrn_Wilson_B_factor 3.63 _oxford_diffrn_Wilson_scale 87.71 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_diff_density_min -0.87 _refine_diff_density_max 0.62 # 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>-10.0\s(I) _refine_ls_number_reflns 6590 _refine_ls_number_restraints 0 _refine_ls_number_parameters 298 _oxford_refine_ls_R_factor_ref 0.1236 _refine_ls_wR_factor_ref 0.1964 _refine_ls_goodness_of_fit_ref 1.1040 _refine_ls_shift/su_max 0.0002211 _refine_ls_shift/su_mean 0.0000205 # The values computed with all filters except I/sigma _oxford_reflns_number_all 6590 _refine_ls_R_factor_all 0.1236 _refine_ls_wR_factor_all 0.1964 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 2650 _refine_ls_R_factor_gt 0.0497 _refine_ls_wR_factor_gt 0.1243 # 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, 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: 2.31 2.97 0.795 ; # 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 S1 S 0.23686(10) 0.48101(5) 0.53818(4) 0.0489 1.0000 Uani . . . . . . C13 C 0.2921(3) 0.49781(16) 0.44878(15) 0.0393 1.0000 Uani . . . . . . N1 N 0.2586(3) 0.56067(13) 0.42537(13) 0.0417 1.0000 Uani . . . . . . C14 C 0.1823(3) 0.59974(17) 0.47934(17) 0.0444 1.0000 Uani . . . . . . C19 C 0.1596(3) 0.56321(18) 0.54529(16) 0.0465 1.0000 Uani . . . . . . C18 C 0.0830(4) 0.5924(2) 0.60532(18) 0.0559 1.0000 Uani . . . . . . C17 C 0.0306(4) 0.6584(2) 0.5977(2) 0.0644 1.0000 Uani . . . . . . C16 C 0.0520(5) 0.6954(2) 0.5327(2) 0.0663 1.0000 Uani . . . . . . C15 C 0.1281(4) 0.66681(19) 0.4730(2) 0.0557 1.0000 Uani . . . . . . B1 B 0.2927(4) 0.58052(18) 0.33802(18) 0.0413 1.0000 Uani . . . . . . O1 O 0.4335(2) 0.53775(11) 0.31852(12) 0.0473 1.0000 Uani . . . . . . C21 C 0.4419(3) 0.47121(16) 0.33683(17) 0.0427 1.0000 Uani . . . . . . C20 C 0.3716(3) 0.44776(16) 0.40338(16) 0.0422 1.0000 Uani . . . . . . C29 C 0.3876(4) 0.37962(17) 0.42397(19) 0.0503 1.0000 Uani . . . . . . C28 C 0.4743(4) 0.33326(18) 0.3810(2) 0.0546 1.0000 Uani . . . . . . C23 C 0.5462(4) 0.35712(17) 0.3155(2) 0.0517 1.0000 Uani . . . . . . C22 C 0.5273(4) 0.42637(18) 0.29496(19) 0.0502 1.0000 Uani . . . . . . C24 C 0.6353(4) 0.3096(2) 0.2727(2) 0.0659 1.0000 Uani . . . . . . C25 C 0.6501(5) 0.2431(2) 0.2941(3) 0.0787 1.0000 Uani . . . . . . C26 C 0.5784(6) 0.2203(2) 0.3568(3) 0.0841 1.0000 Uani . . . . . . C27 C 0.4922(6) 0.2629(2) 0.4008(3) 0.0774 1.0000 Uani . . . . . . C1 C 0.3524(3) 0.65889(16) 0.33219(16) 0.0439 1.0000 Uani . . . . . . C2 C 0.4964(4) 0.67930(19) 0.3694(2) 0.0575 1.0000 Uani . . . . . . C3 C 0.5542(5) 0.7458(2) 0.3660(2) 0.0729 1.0000 Uani . . . . . . C4 C 0.4700(5) 0.7935(2) 0.3235(3) 0.0740 1.0000 Uani . . . . . . C5 C 0.3298(5) 0.7746(2) 0.2857(2) 0.0687 1.0000 Uani . . . . . . C6 C 0.2718(4) 0.70863(19) 0.2899(2) 0.0576 1.0000 Uani . . . . . . C7 C 0.1287(4) 0.56012(16) 0.28986(16) 0.0443 1.0000 Uani . . . . . . C12 C -0.0279(4) 0.58121(17) 0.30714(18) 0.0489 1.0000 Uani . . . . . . C11 C -0.1650(4) 0.56341(19) 0.2641(2) 0.0561 1.0000 Uani . . . . . . C10 C -0.1493(4) 0.5246(2) 0.2015(2) 0.0626 1.0000 Uani . . . . . . C9 C 0.0012(5) 0.5026(2) 0.1829(2) 0.0703 1.0000 Uani . . . . . . C8 C 0.1386(4) 0.52036(19) 0.22579(18) 0.0557 1.0000 Uani . . . . . . H61 H 0.0706 0.5673 0.6490 0.0616 1.0000 Uiso R . . . . . H71 H -0.0198 0.6787 0.6380 0.0720 1.0000 Uiso R . . . . . H81 H 0.0134 0.7392 0.5298 0.0794 1.0000 Uiso R . . . . . H91 H 0.1399 0.6921 0.4295 0.0624 1.0000 Uiso R . . . . . H141 H 0.3382 0.3640 0.4676 0.0567 1.0000 Uiso R . . . . . H171 H 0.5732 0.4408 0.2507 0.0548 1.0000 Uiso R . . . . . H181 H 0.6849 0.3267 0.2298 0.0857 1.0000 Uiso R . . . . . H191 H 0.7100 0.2132 0.2649 0.1062 1.0000 Uiso R . . . . . H231 H 0.5605 0.6468 0.3973 0.0746 1.0000 Uiso R . . . . . H241 H 0.6507 0.7566 0.3942 0.0843 1.0000 Uiso R . . . . . H251 H 0.5099 0.8385 0.3208 0.1006 1.0000 Uiso R . . . . . H261 H 0.2713 0.8067 0.2579 0.0907 1.0000 Uiso R . . . . . H271 H 0.1768 0.6955 0.2629 0.0691 1.0000 Uiso R . . . . . H291 H -0.0379 0.6081 0.3504 0.0606 1.0000 Uiso R . . . . . H301 H -0.2689 0.5788 0.2774 0.0718 1.0000 Uiso R . . . . . H311 H -0.2433 0.5132 0.1716 0.0783 1.0000 Uiso R . . . . . H321 H 0.0117 0.4745 0.1406 0.0835 1.0000 Uiso R . . . . . H331 H 0.2411 0.5047 0.2107 0.0712 1.0000 Uiso R . . . . . H211 H 0.4476 0.2475 0.4445 0.0948 1.0000 Uiso R . . . . . H201 H 0.5847 0.1740 0.3688 0.1049 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 S1 0.0433(4) 0.0629(5) 0.0405(4) 0.0085(4) 0.0004(3) -0.0040(4) C13 0.0303(13) 0.0483(17) 0.0391(14) 0.0042(12) -0.0014(10) -0.0054(11) N1 0.0334(11) 0.0519(16) 0.0398(12) 0.0003(11) 0.0030(9) -0.0035(11) C14 0.0367(14) 0.0519(19) 0.0449(16) -0.0033(13) 0.0045(12) -0.0066(13) C19 0.0348(14) 0.063(2) 0.0415(15) -0.0019(14) -0.0028(11) -0.0083(13) C18 0.0466(17) 0.078(3) 0.0435(17) -0.0055(16) 0.0043(13) -0.0064(16) C17 0.0537(19) 0.084(3) 0.057(2) -0.022(2) 0.0128(16) -0.0063(19) C16 0.063(2) 0.067(2) 0.069(2) -0.0123(19) 0.0127(18) 0.0062(18) C15 0.0588(19) 0.052(2) 0.0568(19) -0.0007(16) 0.0113(15) 0.0021(16) B1 0.0372(16) 0.0446(19) 0.0426(17) 0.0049(14) 0.0069(13) -0.0009(13) O1 0.0383(10) 0.0523(14) 0.0520(12) 0.0059(10) 0.0119(9) -0.0010(9) C21 0.0312(13) 0.0483(18) 0.0487(15) 0.0020(13) 0.0012(11) -0.0034(12) C20 0.0343(13) 0.0442(17) 0.0476(16) 0.0004(13) -0.0043(12) -0.0027(12) C29 0.0466(16) 0.051(2) 0.0525(18) 0.0059(15) -0.0040(13) -0.0069(14) C28 0.0470(17) 0.0492(19) 0.066(2) -0.0010(16) -0.0116(15) -0.0002(14) C23 0.0378(15) 0.051(2) 0.066(2) -0.0109(16) -0.0057(14) -0.0022(13) C22 0.0408(16) 0.054(2) 0.0556(18) -0.0048(15) 0.0054(13) -0.0037(14) C24 0.054(2) 0.062(2) 0.082(3) -0.0179(19) 0.0025(18) 0.0004(17) C25 0.071(3) 0.059(3) 0.106(4) -0.024(2) 0.000(2) 0.007(2) C26 0.090(3) 0.052(3) 0.110(4) -0.010(2) -0.009(3) 0.006(2) C27 0.088(3) 0.063(3) 0.081(3) 0.003(2) -0.006(2) -0.002(2) C1 0.0392(14) 0.0481(17) 0.0450(16) 0.0024(13) 0.0083(12) -0.0030(12) C2 0.0512(18) 0.059(2) 0.062(2) 0.0092(17) -0.0066(15) -0.0084(16) C3 0.062(2) 0.070(3) 0.085(3) -0.005(2) -0.003(2) -0.022(2) C4 0.072(3) 0.056(2) 0.095(3) 0.005(2) 0.019(2) -0.013(2) C5 0.066(2) 0.054(2) 0.087(3) 0.0232(19) 0.008(2) 0.0015(18) C6 0.0453(17) 0.063(2) 0.064(2) 0.0149(17) -0.0006(15) -0.0037(15) C7 0.0415(15) 0.0510(18) 0.0404(15) 0.0079(13) 0.0037(12) -0.0055(13) C12 0.0435(16) 0.0547(19) 0.0487(17) 0.0024(14) 0.0047(13) -0.0052(14) C11 0.0403(16) 0.063(2) 0.065(2) 0.0125(17) 0.0015(14) -0.0063(15) C10 0.056(2) 0.068(2) 0.062(2) 0.0084(19) -0.0129(16) -0.0175(17) C9 0.070(2) 0.088(3) 0.053(2) -0.0138(19) -0.0073(17) -0.006(2) C8 0.0512(18) 0.066(2) 0.0498(17) -0.0063(16) 0.0015(14) -0.0019(16) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.11858(6) 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 S1 . C13 . 1.719(3) yes S1 . C19 . 1.732(4) yes C13 . N1 . 1.323(4) yes C13 . C20 . 1.445(4) yes N1 . C14 . 1.401(4) yes N1 . B1 . 1.652(4) yes C14 . C19 . 1.403(4) yes C14 . C15 . 1.386(5) yes C19 . C18 . 1.392(4) yes C18 . C17 . 1.365(6) yes C18 . H61 . 0.934 no C17 . C16 . 1.391(6) yes C17 . H71 . 0.936 no C16 . C15 . 1.380(5) yes C16 . H81 . 0.914 no C15 . H91 . 0.935 no B1 . O1 . 1.478(4) yes B1 . C1 . 1.612(5) yes B1 . C7 . 1.619(4) yes O1 . C21 . 1.342(4) yes C21 . C20 . 1.425(4) yes C21 . C22 . 1.365(4) yes C20 . C29 . 1.386(4) yes C29 . C28 . 1.403(5) yes C29 . H141 . 0.947 no C28 . C23 . 1.415(5) yes C28 . C27 . 1.426(6) yes C23 . C22 . 1.409(5) yes C23 . C24 . 1.425(5) yes C22 . H171 . 0.937 no C24 . C25 . 1.358(6) yes C24 . H181 . 0.947 no C25 . C26 . 1.368(7) yes C25 . H191 . 0.937 no C26 . C27 . 1.364(6) yes C26 . H201 . 0.930 no C27 . H211 . 0.930 no C1 . C2 . 1.391(4) yes C1 . C6 . 1.386(5) yes C2 . C3 . 1.386(5) yes C2 . H231 . 0.954 no C3 . C4 . 1.373(6) yes C3 . H241 . 0.947 no C4 . C5 . 1.363(6) yes C4 . H251 . 0.940 no C5 . C6 . 1.377(5) yes C5 . H261 . 0.923 no C6 . H271 . 0.936 no C7 . C12 . 1.394(4) yes C7 . C8 . 1.395(5) yes C12 . C11 . 1.383(4) yes C12 . H291 . 0.945 no C11 . C10 . 1.367(5) yes C11 . H301 . 0.942 no C10 . C9 . 1.361(6) yes C10 . H311 . 0.948 no C9 . C8 . 1.384(5) yes C9 . H321 . 0.944 no C8 . H331 . 0.943 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 C13 . S1 . C19 . 90.15(15) yes S1 . C13 . N1 . 114.6(2) yes S1 . C13 . C20 . 122.7(2) yes N1 . C13 . C20 . 122.7(3) yes C13 . N1 . C14 . 112.2(2) yes C13 . N1 . B1 . 118.7(2) yes C14 . N1 . B1 . 128.9(3) yes N1 . C14 . C19 . 112.7(3) yes N1 . C14 . C15 . 127.5(3) yes C19 . C14 . C15 . 119.8(3) yes C14 . C19 . S1 . 110.4(2) yes C14 . C19 . C18 . 121.8(3) yes S1 . C19 . C18 . 127.8(3) yes C19 . C18 . C17 . 117.3(3) yes C19 . C18 . H61 . 120.4 no C17 . C18 . H61 . 122.3 no C18 . C17 . C16 . 121.7(3) yes C18 . C17 . H71 . 118.0 no C16 . C17 . H71 . 120.2 no C17 . C16 . C15 . 121.3(4) yes C17 . C16 . H81 . 118.7 no C15 . C16 . H81 . 120.0 no C14 . C15 . C16 . 118.2(3) yes C14 . C15 . H91 . 121.7 no C16 . C15 . H91 . 120.2 no N1 . B1 . O1 . 104.8(2) yes N1 . B1 . C1 . 110.4(2) yes O1 . B1 . C1 . 106.2(2) yes N1 . B1 . C7 . 106.4(2) yes O1 . B1 . C7 . 111.9(3) yes C1 . B1 . C7 . 116.5(3) yes B1 . O1 . C21 . 121.5(2) yes O1 . C21 . C20 . 119.9(3) yes O1 . C21 . C22 . 120.6(3) yes C20 . C21 . C22 . 119.4(3) yes C13 . C20 . C21 . 117.6(3) yes C13 . C20 . C29 . 122.6(3) yes C21 . C20 . C29 . 119.7(3) yes C20 . C29 . C28 . 121.2(3) yes C20 . C29 . H141 . 119.5 no C28 . C29 . H141 . 119.3 no C29 . C28 . C23 . 118.8(3) yes C29 . C28 . C27 . 122.3(4) yes C23 . C28 . C27 . 118.9(4) yes C28 . C23 . C22 . 119.3(3) yes C28 . C23 . C24 . 118.3(3) yes C22 . C23 . C24 . 122.4(3) yes C23 . C22 . C21 . 121.6(3) yes C23 . C22 . H171 . 117.9 no C21 . C22 . H171 . 120.5 no C23 . C24 . C25 . 120.8(4) yes C23 . C24 . H181 . 117.2 no C25 . C24 . H181 . 122.0 no C24 . C25 . C26 . 120.6(4) yes C24 . C25 . H191 . 118.8 no C26 . C25 . H191 . 120.6 no C25 . C26 . C27 . 121.9(4) yes C25 . C26 . H201 . 119.1 no C27 . C26 . H201 . 119.0 no C28 . C27 . C26 . 119.6(5) yes C28 . C27 . H211 . 118.9 no C26 . C27 . H211 . 121.5 no B1 . C1 . C2 . 119.7(3) yes B1 . C1 . C6 . 124.2(3) yes C2 . C1 . C6 . 116.1(3) yes C1 . C2 . C3 . 122.2(3) yes C1 . C2 . H231 . 120.0 no C3 . C2 . H231 . 117.8 no C2 . C3 . C4 . 119.7(4) yes C2 . C3 . H241 . 117.7 no C4 . C3 . H241 . 122.5 no C3 . C4 . C5 . 119.3(4) yes C3 . C4 . H251 . 119.7 no C5 . C4 . H251 . 121.0 no C4 . C5 . C6 . 120.8(4) yes C4 . C5 . H261 . 119.7 no C6 . C5 . H261 . 119.4 no C1 . C6 . C5 . 121.9(3) yes C1 . C6 . H271 . 117.5 no C5 . C6 . H271 . 120.6 no B1 . C7 . C12 . 124.0(3) yes B1 . C7 . C8 . 120.3(3) yes C12 . C7 . C8 . 115.7(3) yes C7 . C12 . C11 . 122.4(3) yes C7 . C12 . H291 . 117.3 no C11 . C12 . H291 . 120.3 no C12 . C11 . C10 . 119.9(3) yes C12 . C11 . H301 . 120.0 no C10 . C11 . H301 . 120.0 no C11 . C10 . C9 . 119.6(3) yes C11 . C10 . H311 . 119.8 no C9 . C10 . H311 . 120.7 no C10 . C9 . C8 . 120.6(4) yes C10 . C9 . H321 . 119.6 no C8 . C9 . H321 . 119.8 no C7 . C8 . C9 . 121.8(3) yes C7 . C8 . H331 . 119.9 no C9 . C8 . H331 . 118.2 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 C15 . H91 . C1 . 121.75(11) 0.935 2.599 3.192(5) yes _iucr_refine_instruction_details_constraints ; # # Punched on 18/01/13 at 16:40:16 # #LIST 12 BLOCK SCALE X'S, U'S RIDE C ( 18,X'S) H ( 61,X'S) RIDE C ( 17,X'S) H ( 71,X'S) RIDE C ( 16,X'S) H ( 81,X'S) RIDE C ( 15,X'S) H ( 91,X'S) RIDE C ( 29,X'S) H ( 141,X'S) RIDE C ( 22,X'S) H ( 171,X'S) RIDE C ( 24,X'S) H ( 181,X'S) RIDE C ( 25,X'S) H ( 191,X'S) RIDE C ( 26,X'S) H ( 201,X'S) RIDE C ( 27,X'S) H ( 211,X'S) RIDE C ( 2,X'S) H ( 231,X'S) RIDE C ( 3,X'S) H ( 241,X'S) RIDE C ( 4,X'S) H ( 251,X'S) RIDE C ( 5,X'S) H ( 261,X'S) RIDE C ( 6,X'S) H ( 271,X'S) RIDE C ( 12,X'S) H ( 291,X'S) RIDE C ( 11,X'S) H ( 301,X'S) RIDE C ( 10,X'S) H ( 311,X'S) RIDE C ( 9,X'S) H ( 321,X'S) RIDE C ( 8,X'S) H ( 331,X'S) END ; _iucr_refine_instruction_details_restraints ; # # Punched on 18/01/13 at 16:40:16 # #LIST 16 NO REM HREST START (DO NOT REMOVE THIS LINE) REM HREST END (DO NOT REMOVE THIS LINE) END ; # Manually omitted reflections loop_ _oxford_refln_omitted_index_h _oxford_refln_omitted_index_k _oxford_refln_omitted_index_l _oxford_refln_omitted_flag _oxford_refln_omitted_details 0 4 0 x . 0 5 1 x . -1 0 3 x . 1 0 3 x . 0 6 0 x . _database_code_depnum_ccdc_archive 'CCDC 949541'