# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry # 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_global #TrackingRef '4-phenyl-7-(phenylthio)-5H-pyrrolo[3,2-d]pyrimidine.cif' _audit_creation_date 13-02-26 _audit_creation_method CRYSTALS_ver_14.40 _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 6.8659(2) _cell_length_b 18.4844(5) _cell_length_c 11.9993(4) _cell_angle_alpha 90 _cell_angle_beta 103.118(3) _cell_angle_gamma 90 _cell_volume 1483.11(8) _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_int_tables_number 14 # 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 . _symmetry_space_group_name_Hall ? 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 0.0181 0.0091 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0311 0.0180 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4' S 0.3331 0.5567 6.9053 1.4679 5.2034 22.2151 1.4379 0.2536 1.5863 56.1720 0.8669 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 4 _chemical_name_systematic 4-phenyl-7-(phenylthio)-5H-pyrrolo[3,2-d]pyrimidine _chemical_formula_moiety 'C18 H13 N3 S1' # Given Formula = C18 H12 N3 S1 # Dc = 1.35 Fooo = 632.00 Mu = 19.19 M = 302.38 # Found Formula = C18 H13 N3 S1 # Dc = 1.36 FOOO = 632.00 Mu = 19.19 M = 303.39 _chemical_formula_sum 'C18 H13 N3 S1' _chemical_compound_source ? _chemical_formula_weight 303.39 _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _cell_measurement_temperature 190 _exptl_crystal_description plate _exptl_crystal_colour 'pale orange' _diffrn_ambient_temperature 190 _exptl_crystal_size_min 0.035 _exptl_crystal_size_mid 0.420 _exptl_crystal_size_max 0.590 _exptl_crystal_density_diffrn 1.359 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 632 _exptl_absorpt_coefficient_mu 1.919 # Sheldrick geometric approximatio 0.45 0.94 # No experimental values of Tmin/max available _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'CrysAlis, (Oxford Diffraction, 2002)' _exptl_absorpt_correction_T_min 0.45 _exptl_absorpt_correction_T_max 0.94 _diffrn_measurement_device_type 'Oxford Diffraction XCALIBUR' _diffrn_measurement_device Area _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54184 _diffrn_measurement_method '\f & \w scans' # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'Xcalibur, (Oxford Diffraction, 2002)' _computing_cell_refinement 'CrysAlis, (Oxford Diffraction, 2002)' _computing_data_reduction 'CrysAlis, (Oxford Diffraction, 2002)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time . _diffrn_standards_interval_count . _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_reflns_number 6709 _reflns_number_total 3014 _diffrn_reflns_av_R_equivalents 0.029 # Number of reflections without Friedels Law is 0 # Number of reflections with Friedels Law is 3014 # Theoretical number of reflections is about 6283 _diffrn_reflns_theta_min 4.476 _diffrn_reflns_theta_max 77.154 _diffrn_measured_fraction_theta_max 0.960 _diffrn_reflns_theta_full 68.667 _diffrn_measured_fraction_theta_full 0.995 _diffrn_reflns_limit_h_min -8 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -23 _diffrn_reflns_limit_k_max 21 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 15 _reflns_limit_h_min -8 _reflns_limit_h_max 8 _reflns_limit_k_min 0 _reflns_limit_k_max 23 _reflns_limit_l_min 0 _reflns_limit_l_max 15 _oxford_diffrn_Wilson_B_factor 2.70 _oxford_diffrn_Wilson_scale 0.01 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_diff_density_min -0.31 _refine_diff_density_max 0.19 # 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>2.0\s(I) _refine_ls_number_reflns 2707 _refine_ls_number_restraints 0 _refine_ls_number_parameters 200 _oxford_refine_ls_R_factor_ref 0.0369 _refine_ls_wR_factor_ref 0.0467 _refine_ls_goodness_of_fit_ref 1.0035 _refine_ls_shift/su_max 0.0004148 _refine_ls_shift/su_mean 0.0000632 # The values computed with all filters except I/sigma _oxford_reflns_number_all 3014 _refine_ls_R_factor_all 0.0408 _refine_ls_wR_factor_all 0.0484 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 2707 _refine_ls_R_factor_gt 0.0369 _refine_ls_wR_factor_gt 0.0467 _refine_ls_structure_factor_coef F _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: 19.7 -7.13 17.2 ; # 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 N1 N 0.25380(17) 0.81190(6) 0.28095(9) 0.0326 1.0000 Uani . . . . . . C2 C 0.0945(2) 0.77563(8) 0.22135(10) 0.0350 1.0000 Uani . . . . . . N3 N -0.04715(16) 0.74186(6) 0.26037(8) 0.0315 1.0000 Uani . . . . . . C4 C -0.01693(18) 0.74258(6) 0.37560(10) 0.0272 1.0000 Uani . . . . . . C5 C 0.14881(18) 0.77748(6) 0.44639(10) 0.0274 1.0000 Uani . . . . . . C6 C 0.28299(18) 0.81518(6) 0.39581(9) 0.0277 1.0000 Uani . . . . . . N7 N 0.13606(16) 0.76654(6) 0.55823(8) 0.0304 1.0000 Uani . . . . . . C8 C -0.03042(19) 0.72659(7) 0.55841(10) 0.0318 1.0000 Uani . . . . . . C9 C -0.13166(18) 0.71115(7) 0.44819(10) 0.0300 1.0000 Uani . . . . . . C10 C 0.45364(19) 0.85886(7) 0.45784(10) 0.0305 1.0000 Uani . . . . . . C11 C 0.4510(2) 0.89307(8) 0.56086(11) 0.0393 1.0000 Uani . . . . . . C12 C 0.6128(3) 0.93443(9) 0.61601(13) 0.0499 1.0000 Uani . . . . . . C13 C 0.7795(3) 0.94147(9) 0.56957(14) 0.0496 1.0000 Uani . . . . . . C14 C 0.7816(2) 0.90876(8) 0.46633(13) 0.0435 1.0000 Uani . . . . . . C15 C 0.6197(2) 0.86793(7) 0.41051(11) 0.0352 1.0000 Uani . . . . . . S16 S -0.37021(5) 0.673505(17) 0.40700(3) 0.0353 1.0000 Uani . . . . . . C17 C -0.3299(2) 0.58097(7) 0.38060(10) 0.0344 1.0000 Uani . . . . . . C18 C -0.4949(2) 0.53608(8) 0.36941(13) 0.0449 1.0000 Uani . . . . . . C19 C -0.4796(3) 0.46298(9) 0.34707(15) 0.0522 1.0000 Uani . . . . . . C20 C -0.2994(3) 0.43449(9) 0.33720(15) 0.0559 1.0000 Uani . . . . . . C21 C -0.1354(3) 0.47873(10) 0.3486(2) 0.0685 1.0000 Uani . . . . . . C22 C -0.1495(3) 0.55234(9) 0.36971(18) 0.0561 1.0000 Uani . . . . . . H81 H -0.0666 0.7128 0.6265 0.0360 1.0000 Uiso R . . . . . H21 H 0.0787 0.7755 0.1378 0.0399 1.0000 Uiso R . . . . . H151 H 0.6191 0.8463 0.3386 0.0403 1.0000 Uiso R . . . . . H141 H 0.8924 0.9152 0.4335 0.0498 1.0000 Uiso R . . . . . H131 H 0.8900 0.9700 0.6090 0.0576 1.0000 Uiso R . . . . . H121 H 0.6087 0.9582 0.6864 0.0574 1.0000 Uiso R . . . . . H111 H 0.3388 0.8876 0.5933 0.0448 1.0000 Uiso R . . . . . H181 H -0.6200 0.5567 0.3787 0.0511 1.0000 Uiso R . . . . . H191 H -0.5948 0.4329 0.3421 0.0607 1.0000 Uiso R . . . . . H201 H -0.2878 0.3840 0.3220 0.0639 1.0000 Uiso R . . . . . H211 H -0.0112 0.4588 0.3407 0.0804 1.0000 Uiso R . . . . . H221 H -0.0340 0.5816 0.3780 0.0642 1.0000 Uiso R . . . . . H71 H 0.2289 0.7789 0.6201 0.0356 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 N1 0.0332(5) 0.0410(5) 0.0238(5) 0.0012(4) 0.0067(4) 0.0001(4) C2 0.0378(7) 0.0464(7) 0.0202(5) 0.0001(5) 0.0056(5) -0.0001(5) N3 0.0324(5) 0.0402(5) 0.0202(5) -0.0010(4) 0.0026(4) 0.0009(4) C4 0.0287(6) 0.0304(5) 0.0212(5) 0.0003(4) 0.0028(4) 0.0031(4) C5 0.0282(6) 0.0317(5) 0.0209(5) 0.0003(4) 0.0029(4) 0.0041(4) C6 0.0298(6) 0.0300(5) 0.0224(5) 0.0014(4) 0.0044(4) 0.0042(4) N7 0.0308(5) 0.0402(5) 0.0189(5) 0.0011(4) 0.0031(4) -0.0013(4) C8 0.0341(6) 0.0377(6) 0.0241(5) 0.0020(4) 0.0074(5) 0.0020(5) C9 0.0306(6) 0.0325(6) 0.0262(5) 0.0012(4) 0.0050(4) 0.0010(5) C10 0.0332(6) 0.0283(5) 0.0288(6) 0.0031(4) 0.0041(5) 0.0016(5) C11 0.0456(7) 0.0419(7) 0.0310(6) -0.0035(5) 0.0101(5) -0.0069(6) C12 0.0612(10) 0.0502(8) 0.0364(7) -0.0099(6) 0.0071(6) -0.0175(7) C13 0.0509(9) 0.0469(8) 0.0474(8) -0.0035(6) 0.0037(6) -0.0176(7) C14 0.0384(7) 0.0419(7) 0.0508(8) 0.0012(6) 0.0111(6) -0.0072(6) C15 0.0363(7) 0.0338(6) 0.0362(6) -0.0002(5) 0.0094(5) 0.0005(5) S16 0.02906(19) 0.03658(19) 0.0395(2) -0.00280(12) 0.00598(13) -0.00029(11) C17 0.0392(7) 0.0376(6) 0.0258(5) -0.0004(5) 0.0062(5) -0.0021(5) C18 0.0421(8) 0.0451(8) 0.0467(8) -0.0022(6) 0.0084(6) -0.0052(6) C19 0.0593(10) 0.0435(8) 0.0543(9) -0.0059(7) 0.0138(7) -0.0127(7) C20 0.0749(12) 0.0373(7) 0.0593(10) -0.0060(7) 0.0235(9) -0.0029(7) C21 0.0613(11) 0.0471(9) 0.1058(16) -0.0124(9) 0.0371(11) 0.0052(8) C22 0.0468(8) 0.0432(8) 0.0848(12) -0.0090(8) 0.0288(8) -0.0026(7) _refine_ls_extinction_coef 34(7) _refine_ls_extinction_method 'Larson (1970), Equation 22' _oxford_refine_ls_scale 8.58(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 N1 . C2 . 1.3425(18) yes N1 . C6 . 1.3484(15) yes C2 . N3 . 1.3272(18) yes C2 . H21 . 0.984 no N3 . C4 . 1.3509(15) yes C4 . C5 . 1.4121(17) yes C4 . C9 . 1.4241(17) yes C5 . C6 . 1.3987(17) yes C5 . N7 . 1.3794(15) yes C6 . C10 . 1.4774(17) yes N7 . C8 . 1.3613(17) yes N7 . H71 . 0.892 no C8 . C9 . 1.3771(17) yes C8 . H81 . 0.941 no C9 . S16 . 1.7446(13) yes C10 . C11 . 1.3923(18) yes C10 . C15 . 1.3947(19) yes C11 . C12 . 1.386(2) yes C11 . H111 . 0.944 no C12 . C13 . 1.388(3) yes C12 . H121 . 0.958 no C13 . C14 . 1.381(2) yes C13 . H131 . 0.956 no C14 . C15 . 1.3838(19) yes C14 . H141 . 0.940 no C15 . H151 . 0.950 no S16 . C17 . 1.7727(14) yes C17 . C18 . 1.386(2) yes C17 . C22 . 1.380(2) yes C18 . C19 . 1.386(2) yes C18 . H181 . 0.969 no C19 . C20 . 1.374(3) yes C19 . H191 . 0.957 no C20 . C21 . 1.373(3) yes C20 . H201 . 0.957 no C21 . C22 . 1.391(2) yes C21 . H211 . 0.954 no C22 . H221 . 0.946 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C2 . N1 . C6 . 118.76(11) yes N1 . C2 . N3 . 128.36(11) yes N1 . C2 . H21 . 115.6 no N3 . C2 . H21 . 116.0 no C2 . N3 . C4 . 113.70(11) yes N3 . C4 . C5 . 122.40(11) yes N3 . C4 . C9 . 130.11(11) yes C5 . C4 . C9 . 107.49(10) yes C4 . C5 . C6 . 119.13(11) yes C4 . C5 . N7 . 107.33(10) yes C6 . C5 . N7 . 133.52(11) yes C5 . C6 . N1 . 117.48(11) yes C5 . C6 . C10 . 125.36(10) yes N1 . C6 . C10 . 117.16(11) yes C5 . N7 . C8 . 108.65(10) yes C5 . N7 . H71 . 125.5 no C8 . N7 . H71 . 125.4 no N7 . C8 . C9 . 110.60(11) yes N7 . C8 . H81 . 122.4 no C9 . C8 . H81 . 127.0 no C4 . C9 . C8 . 105.91(11) yes C4 . C9 . S16 . 127.12(9) yes C8 . C9 . S16 . 126.26(10) yes C6 . C10 . C11 . 121.79(12) yes C6 . C10 . C15 . 119.26(11) yes C11 . C10 . C15 . 118.92(12) yes C10 . C11 . C12 . 120.25(14) yes C10 . C11 . H111 . 119.6 no C12 . C11 . H111 . 120.2 no C11 . C12 . C13 . 120.28(14) yes C11 . C12 . H121 . 119.6 no C13 . C12 . H121 . 120.2 no C12 . C13 . C14 . 119.76(14) yes C12 . C13 . H131 . 119.1 no C14 . C13 . H131 . 121.1 no C13 . C14 . C15 . 120.14(14) yes C13 . C14 . H141 . 119.6 no C15 . C14 . H141 . 120.2 no C10 . C15 . C14 . 120.62(12) yes C10 . C15 . H151 . 118.9 no C14 . C15 . H151 . 120.5 no C9 . S16 . C17 . 105.11(6) yes S16 . C17 . C18 . 115.95(11) yes S16 . C17 . C22 . 124.54(11) yes C18 . C17 . C22 . 119.50(14) yes C17 . C18 . C19 . 120.41(15) yes C17 . C18 . H181 . 118.7 no C19 . C18 . H181 . 120.9 no C18 . C19 . C20 . 119.96(16) yes C18 . C19 . H191 . 118.7 no C20 . C19 . H191 . 121.3 no C19 . C20 . C21 . 119.80(15) yes C19 . C20 . H201 . 120.3 no C21 . C20 . H201 . 119.9 no C20 . C21 . C22 . 120.75(18) yes C20 . C21 . H211 . 119.4 no C22 . C21 . H211 . 119.8 no C21 . C22 . C17 . 119.56(16) yes C21 . C22 . H221 . 119.1 no C17 . C22 . H221 . 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 C8 . H81 . N1 4_465 165.50(4) 0.941 2.491 3.410(2) yes N7 . H71 . N3 4_565 154.19(4) 0.892 2.042 2.871(2) yes _database_code_depnum_ccdc_archive 'CCDC 926543' ####################################################################### # # 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_global #TrackingRef '4-phenyl-7-(phenylthio)-5H-pyrrolo[3,2-d]pyrimidine.cif' _audit_creation_date 13-02-26 _audit_creation_method CRYSTALS_ver_14.40 _chemical_name_systematic ? _chemical_melting_point ? # Attachment '7-benzyl-4-phenyl-5-(phenylthio)-7H-pyrrolo[2,3-d]pyrimidine.cif' data_2 _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 5.9059(3) _cell_length_b 13.5680(5) _cell_length_c 24.5309(9) _cell_angle_alpha 90 _cell_angle_beta 91.499(4) _cell_angle_gamma 90 _cell_volume 1965.01(13) _symmetry_cell_setting monoclinic _symmetry_space_group_name_H-M 'P 21/n' _symmetry_int_tables_number 14 # 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 . _symmetry_space_group_name_Hall ? 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 0.0181 0.0091 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0311 0.0180 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4' S 0.3331 0.5567 6.9053 1.4679 5.2034 22.2151 1.4379 0.2536 1.5863 56.1720 0.8669 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 4 _chemical_name_systematic 7-benzyl-4-phenyl-5-(phenylthio)-7H-pyrrolo[2,3-d]pyrimidine _chemical_formula_moiety 'C25 H19 N3 S1' # Given Formula = C25 H20 N3 S1 # Dc = 1.33 Fooo = 824.00 Mu = 15.78 M = 394.52 # Found Formula = C25 H19 N3 S1 # Dc = 1.33 FOOO = 824.00 Mu = 15.77 M = 393.51 _chemical_formula_sum 'C25 H19 N3 S1' _chemical_compound_source ? _chemical_formula_weight 393.51 _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _cell_measurement_temperature 190 _exptl_crystal_description block _exptl_crystal_colour colourless _diffrn_ambient_temperature 190 _exptl_crystal_size_min 0.050 _exptl_crystal_size_mid 0.130 _exptl_crystal_size_max 0.210 _exptl_crystal_density_diffrn 1.330 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 824 _exptl_absorpt_coefficient_mu 1.577 # Sheldrick geometric approximatio 0.81 0.92 _exptl_absorpt_correction_type multi-scan _exptl_absorpt_process_details 'CrysAlis, (Oxford Diffraction, 2002)' _exptl_absorpt_correction_T_min 0.81 _exptl_absorpt_correction_T_max 0.92 _diffrn_measurement_device_type 'Oxford Diffraction XCALIBUR' _diffrn_measurement_device Area _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type 'Cu K\a' _diffrn_radiation_wavelength 1.54184 _diffrn_measurement_method '\f & \w scans' # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'Xcalibur, (Oxford Diffraction, 2002)' _computing_cell_refinement 'CrysAlis, (Oxford Diffraction, 2002)' _computing_data_reduction 'CrysAlis, (Oxford Diffraction, 2002)' _computing_structure_solution 'SIR92 (Altomare et al., 1994)' _computing_structure_refinement 'CRYSTALS (Betteridge et al., 2003)' _computing_publication_material 'CRYSTALS (Betteridge et al., 2003)' _computing_molecular_graphics 'CAMERON (Watkin et al., 1996)' _diffrn_standards_interval_time . _diffrn_standards_interval_count . _diffrn_standards_number 0 _diffrn_standards_decay_% ? _diffrn_reflns_number 9133 _reflns_number_total 4031 _diffrn_reflns_av_R_equivalents 0.030 # Number of reflections without Friedels Law is 0 # Number of reflections with Friedels Law is 4031 # Theoretical number of reflections is about 8317 _diffrn_reflns_theta_min 4.861 _diffrn_reflns_theta_max 77.079 _diffrn_measured_fraction_theta_max 0.968 _diffrn_reflns_theta_full 69.371 _diffrn_measured_fraction_theta_full 0.996 _diffrn_reflns_limit_h_min -6 _diffrn_reflns_limit_h_max 7 _diffrn_reflns_limit_k_min -16 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -30 _diffrn_reflns_limit_l_max 26 _reflns_limit_h_min -7 _reflns_limit_h_max 7 _reflns_limit_k_min 0 _reflns_limit_k_max 16 _reflns_limit_l_min 0 _reflns_limit_l_max 30 _oxford_diffrn_Wilson_B_factor 2.47 _oxford_diffrn_Wilson_scale 0.06 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens difmap _refine_diff_density_min -0.28 _refine_diff_density_max 0.24 # 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>2.0\s(I) _refine_ls_number_reflns 3473 _refine_ls_number_restraints 0 _refine_ls_number_parameters 263 _oxford_refine_ls_R_factor_ref 0.0392 _refine_ls_wR_factor_ref 0.0502 _refine_ls_goodness_of_fit_ref 1.0885 _refine_ls_shift/su_max 0.0026037 _refine_ls_shift/su_mean 0.0000843 # The values computed with all filters except I/sigma _oxford_reflns_number_all 4031 _refine_ls_R_factor_all 0.0463 _refine_ls_wR_factor_all 0.0557 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 3473 _refine_ls_R_factor_gt 0.0392 _refine_ls_wR_factor_gt 0.0502 _refine_ls_structure_factor_coef F _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: 14.0 14.1 13.1 4.77 ; # 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 N1 N 0.39491(17) 0.89157(8) 0.31289(5) 0.0339 1.0000 Uani . . . . . . C2 C 0.3460(2) 0.80095(10) 0.33092(6) 0.0360 1.0000 Uani . . . . . . N3 N 0.46651(18) 0.74415(8) 0.36520(5) 0.0350 1.0000 Uani . . . . . . C4 C 0.6529(2) 0.78888(9) 0.38418(5) 0.0296 1.0000 Uani . . . . . . C5 C 0.72327(19) 0.88551(9) 0.37106(5) 0.0272 1.0000 Uani . . . . . . C6 C 0.5875(2) 0.93474(9) 0.33191(5) 0.0291 1.0000 Uani . . . . . . C7 C 0.92160(19) 0.90520(9) 0.40512(5) 0.0273 1.0000 Uani . . . . . . C8 C 0.9639(2) 0.82118(9) 0.43418(5) 0.0299 1.0000 Uani . . . . . . N9 N 0.80436(18) 0.74996(8) 0.42143(5) 0.0323 1.0000 Uani . . . . . . C10 C 0.6455(2) 1.03203(10) 0.30908(5) 0.0301 1.0000 Uani . . . . . . C11 C 0.8575(2) 1.04815(11) 0.28688(5) 0.0373 1.0000 Uani . . . . . . C12 C 0.9076(2) 1.13872(13) 0.26431(6) 0.0462 1.0000 Uani . . . . . . C13 C 0.7509(3) 1.21459(12) 0.26475(6) 0.0464 1.0000 Uani . . . . . . C14 C 0.5410(3) 1.19936(11) 0.28685(6) 0.0418 1.0000 Uani . . . . . . C15 C 0.4866(2) 1.10800(10) 0.30831(5) 0.0342 1.0000 Uani . . . . . . S16 S 1.09114(5) 1.01035(2) 0.410375(12) 0.0295 1.0000 Uani . . . . . . C17 C 0.8945(2) 1.10335(9) 0.42741(5) 0.0272 1.0000 Uani . . . . . . C18 C 0.9489(2) 1.20000(10) 0.41370(5) 0.0347 1.0000 Uani . . . . . . C19 C 0.8030(3) 1.27635(10) 0.42657(6) 0.0424 1.0000 Uani . . . . . . C20 C 0.6027(3) 1.25612(11) 0.45285(6) 0.0431 1.0000 Uani . . . . . . C21 C 0.5484(2) 1.15993(10) 0.46628(6) 0.0368 1.0000 Uani . . . . . . C22 C 0.6937(2) 1.08339(9) 0.45386(5) 0.0303 1.0000 Uani . . . . . . C23 C 0.8010(2) 0.64934(10) 0.44256(6) 0.0377 1.0000 Uani . . . . . . C24 C 0.9626(2) 0.58174(9) 0.41395(6) 0.0348 1.0000 Uani . . . . . . C25 C 1.1568(3) 0.54829(10) 0.44108(7) 0.0420 1.0000 Uani . . . . . . C26 C 1.3085(3) 0.48815(11) 0.41508(9) 0.0549 1.0000 Uani . . . . . . C27 C 1.2672(4) 0.46083(14) 0.36175(10) 0.0676 1.0000 Uani . . . . . . C28 C 1.0742(5) 0.49298(14) 0.33438(8) 0.0689 1.0000 Uani . . . . . . C29 C 0.9213(4) 0.55327(12) 0.36053(7) 0.0539 1.0000 Uani . . . . . . H181 H 1.0862 1.2137 0.3951 0.0389 1.0000 Uiso R . . . . . H191 H 0.8399 1.3422 0.4165 0.0477 1.0000 Uiso R . . . . . H201 H 0.4992 1.3081 0.4614 0.0490 1.0000 Uiso R . . . . . H211 H 0.4070 1.1456 0.4841 0.0415 1.0000 Uiso R . . . . . H221 H 0.6573 1.0162 0.4637 0.0335 1.0000 Uiso R . . . . . H81 H 1.0874 0.8108 0.4612 0.0332 1.0000 Uiso R . . . . . H231 H 0.8487 0.6522 0.4831 0.0427 1.0000 Uiso R . . . . . H232 H 0.6438 0.6234 0.4380 0.0437 1.0000 Uiso R . . . . . H251 H 1.1824 0.5676 0.4784 0.0483 1.0000 Uiso R . . . . . H261 H 1.4387 0.4649 0.4331 0.0615 1.0000 Uiso R . . . . . H271 H 1.3758 0.4202 0.3447 0.0755 1.0000 Uiso R . . . . . H281 H 1.0435 0.4731 0.2975 0.0793 1.0000 Uiso R . . . . . H291 H 0.7894 0.5770 0.3417 0.0599 1.0000 Uiso R . . . . . H21 H 0.2022 0.7740 0.3163 0.0396 1.0000 Uiso R . . . . . H151 H 0.3410 1.0965 0.3230 0.0400 1.0000 Uiso R . . . . . H141 H 0.4292 1.2515 0.2867 0.0468 1.0000 Uiso R . . . . . H131 H 0.7892 1.2764 0.2498 0.0527 1.0000 Uiso R . . . . . H121 H 1.0538 1.1494 0.2494 0.0515 1.0000 Uiso R . . . . . H111 H 0.9684 0.9963 0.2882 0.0414 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 N1 0.0281(5) 0.0383(6) 0.0354(5) -0.0061(4) 0.0006(4) 0.0018(4) C2 0.0291(6) 0.0379(7) 0.0410(7) -0.0099(5) 0.0018(5) -0.0024(5) N3 0.0325(5) 0.0304(5) 0.0423(6) -0.0067(4) 0.0049(4) -0.0028(4) C4 0.0295(6) 0.0264(6) 0.0333(6) -0.0038(5) 0.0059(5) 0.0008(4) C5 0.0256(5) 0.0255(6) 0.0308(6) -0.0033(4) 0.0048(4) 0.0018(4) C6 0.0264(5) 0.0322(6) 0.0290(5) -0.0041(4) 0.0041(4) 0.0037(4) C7 0.0246(5) 0.0267(6) 0.0307(5) -0.0013(4) 0.0035(4) 0.0016(4) C8 0.0282(6) 0.0273(6) 0.0344(6) -0.0016(5) 0.0033(5) 0.0032(4) N9 0.0334(5) 0.0239(5) 0.0398(6) 0.0012(4) 0.0029(4) 0.0011(4) C10 0.0269(6) 0.0367(6) 0.0267(5) 0.0020(5) 0.0006(4) 0.0015(5) C11 0.0279(6) 0.0490(8) 0.0352(6) 0.0071(6) 0.0027(5) 0.0036(5) C12 0.0322(6) 0.0646(10) 0.0418(7) 0.0195(7) 0.0025(5) -0.0043(6) C13 0.0472(8) 0.0481(8) 0.0435(8) 0.0197(7) -0.0032(6) -0.0086(6) C14 0.0437(8) 0.0389(7) 0.0429(7) 0.0094(6) 0.0006(6) 0.0048(6) C15 0.0311(6) 0.0375(7) 0.0343(6) 0.0048(5) 0.0028(5) 0.0031(5) S16 0.02350(17) 0.02751(17) 0.03746(18) 0.00046(11) 0.00247(11) -0.00038(10) C17 0.0281(5) 0.0251(6) 0.0283(5) -0.0001(4) -0.0022(4) -0.0011(4) C18 0.0375(7) 0.0301(6) 0.0365(6) 0.0033(5) 0.0044(5) -0.0034(5) C19 0.0546(8) 0.0249(6) 0.0477(8) 0.0035(5) 0.0032(6) 0.0015(6) C20 0.0468(8) 0.0332(7) 0.0493(8) -0.0028(6) 0.0039(6) 0.0117(6) C21 0.0336(6) 0.0365(7) 0.0405(7) -0.0041(5) 0.0045(5) 0.0023(5) C22 0.0308(6) 0.0279(6) 0.0322(6) -0.0004(5) 0.0024(5) -0.0008(5) C23 0.0412(7) 0.0262(6) 0.0461(7) 0.0061(5) 0.0081(6) 0.0001(5) C24 0.0410(7) 0.0227(6) 0.0409(7) 0.0043(5) 0.0031(5) -0.0006(5) C25 0.0466(8) 0.0263(6) 0.0527(8) 0.0031(6) -0.0041(6) -0.0016(5) C26 0.0442(9) 0.0303(7) 0.0904(13) 0.0055(7) 0.0051(8) 0.0063(6) C27 0.0779(13) 0.0383(9) 0.0882(14) 0.0003(9) 0.0308(11) 0.0133(9) C28 0.1109(18) 0.0512(10) 0.0450(9) -0.0064(7) 0.0114(10) 0.0144(10) C29 0.0777(11) 0.0420(8) 0.0416(8) 0.0018(6) -0.0062(7) 0.0140(8) _refine_ls_extinction_coef 79(15) _refine_ls_extinction_method 'Larson (1970), Equation 22' _oxford_refine_ls_scale 4.099(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 N1 . C2 . 1.3408(18) yes N1 . C6 . 1.3514(16) yes C2 . N3 . 1.3329(18) yes C2 . H21 . 0.983 no N3 . C4 . 1.3306(16) yes C4 . C5 . 1.4149(16) yes C4 . N9 . 1.3678(17) yes C5 . C6 . 1.4042(17) yes C5 . C7 . 1.4458(16) yes C6 . C10 . 1.4776(18) yes C7 . C8 . 1.3641(18) yes C7 . S16 . 1.7457(12) yes C8 . N9 . 1.3797(17) yes C8 . H81 . 0.983 no N9 . C23 . 1.4605(16) yes C10 . C11 . 1.3956(17) yes C10 . C15 . 1.3938(18) yes C11 . C12 . 1.383(2) yes C11 . H111 . 0.961 no C12 . C13 . 1.384(2) yes C12 . H121 . 0.957 no C13 . C14 . 1.382(2) yes C13 . H131 . 0.945 no C14 . C15 . 1.3877(19) yes C14 . H141 . 0.967 no C15 . H151 . 0.954 no S16 . C17 . 1.7722(12) yes C17 . C18 . 1.3933(17) yes C17 . C22 . 1.3934(16) yes C18 . C19 . 1.3891(19) yes C18 . H181 . 0.959 no C19 . C20 . 1.389(2) yes C19 . H191 . 0.953 no C20 . C21 . 1.386(2) yes C20 . H201 . 0.960 no C21 . C22 . 1.3860(18) yes C21 . H211 . 0.973 no C22 . H221 . 0.969 no C23 . C24 . 1.5100(19) yes C23 . H231 . 1.026 no C23 . H232 . 0.996 no C24 . C25 . 1.387(2) yes C24 . C29 . 1.382(2) yes C25 . C26 . 1.380(2) yes C25 . H251 . 0.961 no C26 . C27 . 1.375(3) yes C26 . H261 . 0.932 no C27 . C28 . 1.379(3) yes C27 . H271 . 0.950 no C28 . C29 . 1.388(3) yes C28 . H281 . 0.957 no C29 . H291 . 0.952 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag C2 . N1 . C6 . 118.05(11) yes N1 . C2 . N3 . 128.48(12) yes N1 . C2 . H21 . 114.3 no N3 . C2 . H21 . 117.2 no C2 . N3 . C4 . 112.35(11) yes N3 . C4 . C5 . 126.04(12) yes N3 . C4 . N9 . 125.32(11) yes C5 . C4 . N9 . 108.60(10) yes C4 . C5 . C6 . 115.50(11) yes C4 . C5 . C7 . 106.14(10) yes C6 . C5 . C7 . 138.33(11) yes C5 . C6 . N1 . 119.37(12) yes C5 . C6 . C10 . 123.38(11) yes N1 . C6 . C10 . 117.24(11) yes C5 . C7 . C8 . 106.37(11) yes C5 . C7 . S16 . 130.41(9) yes C8 . C7 . S16 . 123.20(9) yes C7 . C8 . N9 . 110.63(11) yes C7 . C8 . H81 . 126.5 no N9 . C8 . H81 . 122.9 no C8 . N9 . C4 . 108.16(10) yes C8 . N9 . C23 . 126.14(11) yes C4 . N9 . C23 . 125.68(11) yes C6 . C10 . C11 . 120.48(12) yes C6 . C10 . C15 . 120.20(11) yes C11 . C10 . C15 . 119.30(12) yes C10 . C11 . C12 . 119.92(13) yes C10 . C11 . H111 . 119.3 no C12 . C11 . H111 . 120.7 no C11 . C12 . C13 . 120.51(13) yes C11 . C12 . H121 . 119.4 no C13 . C12 . H121 . 120.0 no C12 . C13 . C14 . 119.91(14) yes C12 . C13 . H131 . 119.3 no C14 . C13 . H131 . 120.7 no C13 . C14 . C15 . 120.09(14) yes C13 . C14 . H141 . 120.6 no C15 . C14 . H141 . 119.3 no C10 . C15 . C14 . 120.22(12) yes C10 . C15 . H151 . 119.2 no C14 . C15 . H151 . 120.6 no C7 . S16 . C17 . 102.78(5) yes S16 . C17 . C18 . 117.17(9) yes S16 . C17 . C22 . 122.85(9) yes C18 . C17 . C22 . 119.98(11) yes C17 . C18 . C19 . 119.92(12) yes C17 . C18 . H181 . 120.0 no C19 . C18 . H181 . 120.1 no C18 . C19 . C20 . 119.93(13) yes C18 . C19 . H191 . 119.5 no C20 . C19 . H191 . 120.5 no C19 . C20 . C21 . 120.10(13) yes C19 . C20 . H201 . 120.8 no C21 . C20 . H201 . 119.1 no C20 . C21 . C22 . 120.34(12) yes C20 . C21 . H211 . 120.2 no C22 . C21 . H211 . 119.5 no C17 . C22 . C21 . 119.74(12) yes C17 . C22 . H221 . 119.7 no C21 . C22 . H221 . 120.5 no N9 . C23 . C24 . 112.84(11) yes N9 . C23 . H231 . 107.6 no C24 . C23 . H231 . 108.2 no N9 . C23 . H232 . 108.1 no C24 . C23 . H232 . 109.4 no H231 . C23 . H232 . 110.7 no C23 . C24 . C25 . 120.04(13) yes C23 . C24 . C29 . 120.82(14) yes C25 . C24 . C29 . 119.13(14) yes C24 . C25 . C26 . 120.67(15) yes C24 . C25 . H251 . 118.4 no C26 . C25 . H251 . 120.9 no C25 . C26 . C27 . 119.87(17) yes C25 . C26 . H261 . 121.3 no C27 . C26 . H261 . 118.9 no C26 . C27 . C28 . 120.11(17) yes C26 . C27 . H271 . 118.0 no C28 . C27 . H271 . 121.9 no C27 . C28 . C29 . 120.07(18) yes C27 . C28 . H281 . 120.3 no C29 . C28 . H281 . 119.6 no C28 . C29 . C24 . 120.14(17) yes C28 . C29 . H291 . 120.6 no C24 . C29 . H291 . 119.3 no _database_code_depnum_ccdc_archive 'CCDC 926544'