# Supplementary Material (ESI) for Organic & Biomolecular Chemistry # This journal is (c) The Royal Society of Chemistry 2009 ####################################################################### # # 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 _database_code_depnum_ccdc_archive 'CCDC 703631' _audit_creation_date 08-09-25 _audit_creation_method CRYSTALS_ver_12.86 _chemical_name_systematic ;(7-benzyl-4-phenyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-7H-pyrrolo[2,3-d]pyrimidine) ; _chemical_formula_moiety 'C25 H26 B1 N3 O2' _chemical_formula_sum 'C25 H26 B1 N3 O2' _exptl_crystal_description prism _exptl_crystal_colour colourless _diffrn_ambient_temperature 298 _cell_length_a 12.0486(3) _cell_length_b 12.5522(3) _cell_length_c 15.7030(4) _cell_angle_alpha 98.5162(18) _cell_angle_beta 97.4398(18) _cell_angle_gamma 103.2928(18) _cell_volume 2252.52(10) _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 0.0181 0.0091 2.3100 20.8439 1.0200 10.2075 1.5886 0.5687 0.8650 51.6512 0.2156 'International Tables Vol C 4.2.6.8 and 6.1.1.4' H 0.0000 0.0000 0.4930 10.5109 0.3229 26.1257 0.1402 3.1424 0.0408 57.7998 0.0030 'International Tables Vol C 4.2.6.8 and 6.1.1.4' B 0.0090 0.0039 2.0545 23.2185 1.3326 1.0210 1.0979 60.3498 0.7068 0.1403 -0.1932 'International Tables Vol C 4.2.6.8 and 6.1.1.4' N 0.0311 0.0180 12.2126 0.0057 3.1322 9.8933 2.0125 28.9975 1.1663 0.5826 -11.5290 'International Tables Vol C 4.2.6.8 and 6.1.1.4' O 0.0492 0.0322 3.0485 13.2771 2.2868 5.7011 1.5463 0.3239 0.8670 32.9089 0.2508 'International Tables Vol C 4.2.6.8 and 6.1.1.4' _cell_formula_units_Z 4 # Given Formula = C25 H26 B1 N3 O2 # Dc = 1.21 Fooo = 872.00 Mu = 6.10 M = 822.62 # Found Formula = C25 H26 B1 N3 O2 # Dc = 1.21 FOOO = 872.00 Mu = 6.10 M = 822.62 _chemical_compound_source ? _chemical_formula_weight 411.31 _cell_measurement_reflns_used 24370 _cell_measurement_theta_min 4 _cell_measurement_theta_max 77 _cell_measurement_temperature 298 _exptl_crystal_size_min 0.24 _exptl_crystal_size_mid 0.28 _exptl_crystal_size_max 0.45 _exptl_crystal_density_diffrn 1.213 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 872 _exptl_absorpt_coefficient_mu 0.610 # Sheldrick geometric approximatio 0.84 0.86 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details ; Analytical Absorption (De Meulenaer & Tompa, 1965) ; _exptl_absorpt_correction_T_min 0.84 _exptl_absorpt_correction_T_max 0.86 _diffrn_measurement_device 'Oxford Diffraction XCALIBUR' _diffrn_measurement_device_type Area _diffrn_radiation_monochromator graphite _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 RED, (Oxford Diffraction, 2002)' _computing_data_reduction 'CrysAlis RED, (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 73819 _reflns_number_total 9449 _diffrn_reflns_av_R_equivalents 0.037 # Number of reflections with Friedels Law is 9449 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 9595 _diffrn_reflns_theta_min 3.681 _diffrn_reflns_theta_max 77.621 _diffrn_measured_fraction_theta_max 0.984 _diffrn_reflns_theta_full 72.963 _diffrn_measured_fraction_theta_full 0.996 _diffrn_reflns_limit_h_min -15 _diffrn_reflns_limit_h_max 15 _diffrn_reflns_limit_k_min -15 _diffrn_reflns_limit_k_max 15 _diffrn_reflns_limit_l_min -19 _diffrn_reflns_limit_l_max 19 _reflns_limit_h_min -15 _reflns_limit_h_max 14 _reflns_limit_k_min -15 _reflns_limit_k_max 15 _reflns_limit_l_min 0 _reflns_limit_l_max 19 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.23 _refine_diff_density_max 0.66 # 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 4276 _refine_ls_number_restraints 0 _refine_ls_number_parameters 560 _oxford_refine_ls_R_factor_ref 0.0589 _refine_ls_wR_factor_ref 0.0675 _refine_ls_goodness_of_fit_ref 1.0755 _refine_ls_shift/su_max 0.000248 # The values computed from all data _oxford_reflns_number_all 9413 _refine_ls_R_factor_all 0.0911 _refine_ls_wR_factor_all 0.0785 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 4276 _refine_ls_R_factor_gt 0.0589 _refine_ls_wR_factor_gt 0.0675 # 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 F _refine_ls_matrix_type full _refine_ls_hydrogen_treatment constr # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, 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: 14.5 3.67 12.7 ; # Insert your own references if required - in alphabetical order loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _oxford_atom_site_special_shape _atom_site_attached_hydrogens B16 B 0.5978(3) 0.3984(3) 0.7886(2) 0.0686 1.0000 Uani . . . . . . . B47 B 0.0298(3) 0.8627(2) 0.7225(2) 0.0613 1.0000 Uani . . . . . . . O17 O 0.5995(2) 0.4619(2) 0.72614(14) 0.0966 1.0000 Uani . . . . . . . O20 O 0.5717(2) 0.28827(18) 0.75706(13) 0.0847 1.0000 Uani . . . . . . . O48 O -0.0198(2) 0.90971(16) 0.78523(14) 0.0846 1.0000 Uani . . . . . . . O51 O 0.02494(18) 0.75384(15) 0.72332(13) 0.0751 1.0000 Uani . . . . . . . N1 N 0.6983(3) 0.6370(3) 1.16768(16) 0.0861 1.0000 Uani . . . . . . . N3 N 0.6997(2) 0.4494(2) 1.11013(16) 0.0814 1.0000 Uani . . . . . . . N9 N 0.6517(2) 0.39861(19) 0.95480(14) 0.0673 1.0000 Uani . . . . . . . N32 N 0.1889(2) 1.1521(2) 0.46102(16) 0.0747 1.0000 Uani . . . . . . . N34 N 0.2093(2) 0.9675(2) 0.46949(16) 0.0731 1.0000 Uani . . . . . . . N40 N 0.13658(18) 0.89434(17) 0.58905(14) 0.0611 1.0000 Uani . . . . . . . C2 C 0.7113(3) 0.5350(3) 1.1735(2) 0.0909 1.0000 Uani . . . . . . . C4 C 0.6703(2) 0.4722(2) 1.03194(17) 0.0650 1.0000 Uani . . . . . . . C5 C 0.6533(2) 0.5749(2) 1.01453(17) 0.0619 1.0000 Uani . . . . . . . C6 C 0.6692(2) 0.6586(2) 1.08728(18) 0.0673 1.0000 Uani . . . . . . . C7 C 0.6244(2) 0.5589(2) 0.92136(17) 0.0651 1.0000 Uani . . . . . . . C8 C 0.6242(2) 0.4523(2) 0.88691(17) 0.0650 1.0000 Uani . . . . . . . C10 C 0.6564(2) 0.7732(3) 1.0853(2) 0.0736 1.0000 Uani . . . . . . . C11 C 0.6228(5) 0.8074(3) 1.0096(3) 0.1143 1.0000 Uani . . . . . . . C12 C 0.6134(5) 0.9157(4) 1.0092(3) 0.1277 1.0000 Uani . . . . . . . C13 C 0.6364(4) 0.9893(4) 1.0856(4) 0.1232 1.0000 Uani . . . . . . . C14 C 0.6650(5) 0.9555(4) 1.1616(4) 0.1384 1.0000 Uani . . . . . . . C15 C 0.6756(4) 0.8485(3) 1.1613(3) 0.1144 1.0000 Uani . . . . . . . C18 C 0.5571(3) 0.3862(3) 0.6428(2) 0.0971 1.0000 Uani . . . . . . . C19 C 0.5724(3) 0.2746(3) 0.6633(2) 0.0954 1.0000 Uani . . . . . . . C21 C 0.4298(4) 0.3871(4) 0.6198(3) 0.1221 1.0000 Uani . . . . . . . C22 C 0.6259(5) 0.4324(5) 0.5765(3) 0.1591 1.0000 Uani . . . . . . . C23 C 0.4803(5) 0.1756(4) 0.6165(3) 0.1426 1.0000 Uani . . . . . . . C24 C 0.6936(5) 0.2599(6) 0.6546(4) 0.1700 1.0000 Uani . . . . . . . C25 C 0.6702(3) 0.2866(2) 0.9461(2) 0.0753 1.0000 Uani . . . . . . . C26 C 0.7807(3) 0.2780(2) 0.91291(18) 0.0690 1.0000 Uani . . . . . . . C27 C 0.8739(3) 0.3668(3) 0.9212(2) 0.0782 1.0000 Uani . . . . . . . C28 C 0.9751(3) 0.3541(3) 0.8932(2) 0.0932 1.0000 Uani . . . . . . . C29 C 0.9852(4) 0.2516(4) 0.8583(3) 0.0976 1.0000 Uani . . . . . . . C30 C 0.8931(4) 0.1619(4) 0.8488(3) 0.1072 1.0000 Uani . . . . . . . C31 C 0.7913(3) 0.1740(3) 0.8757(2) 0.0921 1.0000 Uani . . . . . . . C33 C 0.2189(3) 1.0578(3) 0.4348(2) 0.0782 1.0000 Uani . . . . . . . C35 C 0.1601(2) 0.9757(2) 0.54083(17) 0.0606 1.0000 Uani . . . . . . . C36 C 0.1226(2) 1.0683(2) 0.57731(16) 0.0574 1.0000 Uani . . . . . . . C37 C 0.1399(2) 1.1588(2) 0.53332(17) 0.0607 1.0000 Uani . . . . . . . C38 C 0.0742(2) 1.0370(2) 0.65102(17) 0.0622 1.0000 Uani . . . . . . . C39 C 0.0832(2) 0.9311(2) 0.65681(17) 0.0602 1.0000 Uani . . . . . . . C41 C 0.1098(2) 1.2648(2) 0.56110(18) 0.0626 1.0000 Uani . . . . . . . C42 C 0.0410(3) 1.2782(2) 0.6240(2) 0.0780 1.0000 Uani . . . . . . . C43 C 0.0157(3) 1.3787(3) 0.6495(2) 0.0851 1.0000 Uani . . . . . . . C44 C 0.0579(3) 1.4675(3) 0.6136(2) 0.0873 1.0000 Uani . . . . . . . C45 C 0.1239(4) 1.4561(3) 0.5493(3) 0.0992 1.0000 Uani . . . . . . . C46 C 0.1495(3) 1.3564(3) 0.5232(2) 0.0843 1.0000 Uani . . . . . . . C49 C -0.0732(4) 0.8223(3) 0.8281(3) 0.1019 1.0000 Uani . . . . . . . C50 C -0.0260(3) 0.7262(3) 0.7982(2) 0.0897 1.0000 Uani . . . . . . . C52 C -0.2059(5) 0.7890(6) 0.7754(5) 0.1854 1.0000 Uani . . . . . . . C53 C -0.0936(8) 0.8563(5) 0.9119(4) 0.1964 1.0000 Uani . . . . . . . C54 C -0.0867(7) 0.6123(4) 0.7884(5) 0.1802 1.0000 Uani . . . . . . . C55 C 0.0834(6) 0.7358(8) 0.8688(4) 0.1894 1.0000 Uani . . . . . . . C56 C 0.1707(2) 0.7896(2) 0.57505(19) 0.0670 1.0000 Uani . . . . . . . C57 C 0.2844(3) 0.7951(2) 0.6294(2) 0.0699 1.0000 Uani . . . . . . . C58 C 0.3850(3) 0.8602(4) 0.6127(3) 0.1031 1.0000 Uani . . . . . . . C59 C 0.4880(4) 0.8653(6) 0.6649(4) 0.1493 1.0000 Uani . . . . . . . C60 C 0.4919(5) 0.8066(6) 0.7309(4) 0.1512 1.0000 Uani . . . . . . . C61 C 0.3947(4) 0.7429(4) 0.7482(4) 0.1253 1.0000 Uani . . . . . . . C62 C 0.2918(3) 0.7374(3) 0.6975(3) 0.0950 1.0000 Uani . . . . . . . H21 H 0.7278 0.5230 1.2307 0.1119 1.0000 Uiso R . . . . . . H71 H 0.6081 0.6110 0.8873 0.0771 1.0000 Uiso R . . . . . . H111 H 0.6066 0.7565 0.9572 0.1477 1.0000 Uiso R . . . . . . H121 H 0.5928 0.9398 0.9566 0.1694 1.0000 Uiso R . . . . . . H131 H 0.6312 1.0625 1.0860 0.1430 1.0000 Uiso R . . . . . . H141 H 0.6771 1.0053 1.2151 0.1569 1.0000 Uiso R . . . . . . H151 H 0.6973 0.8260 1.2136 0.1292 1.0000 Uiso R . . . . . . H211 H 0.4257 0.4631 0.6210 0.1808 1.0000 Uiso R . . . . . . H212 H 0.3868 0.3566 0.6623 0.1805 1.0000 Uiso R . . . . . . H213 H 0.3976 0.3441 0.5616 0.1806 1.0000 Uiso R . . . . . . H221 H 0.6127 0.5036 0.5709 0.2220 1.0000 Uiso R . . . . . . H222 H 0.6014 0.3812 0.5213 0.2216 1.0000 Uiso R . . . . . . H223 H 0.7065 0.4406 0.5975 0.2216 1.0000 Uiso R . . . . . . H231 H 0.4086 0.1835 0.6347 0.1977 1.0000 Uiso R . . . . . . H232 H 0.4746 0.1702 0.5541 0.1979 1.0000 Uiso R . . . . . . H233 H 0.4987 0.1111 0.6341 0.1982 1.0000 Uiso R . . . . . . H241 H 0.6991 0.2427 0.5937 0.2518 1.0000 Uiso R . . . . . . H242 H 0.7076 0.2021 0.6833 0.2521 1.0000 Uiso R . . . . . . H243 H 0.7502 0.3281 0.6811 0.2518 1.0000 Uiso R . . . . . . H251 H 0.6754 0.2684 1.0045 0.0936 1.0000 Uiso R . . . . . . H252 H 0.6054 0.2348 0.9057 0.0941 1.0000 Uiso R . . . . . . H271 H 0.8687 0.4377 0.9446 0.0943 1.0000 Uiso R . . . . . . H281 H 1.0382 0.4178 0.8985 0.1129 1.0000 Uiso R . . . . . . H291 H 1.0543 0.2415 0.8415 0.1251 1.0000 Uiso R . . . . . . H301 H 0.8989 0.0913 0.8241 0.1373 1.0000 Uiso R . . . . . . H311 H 0.7279 0.1121 0.8689 0.1133 1.0000 Uiso R . . . . . . H331 H 0.2523 1.0546 0.3832 0.0957 1.0000 Uiso R . . . . . . H381 H 0.0422 1.0803 0.6910 0.0763 1.0000 Uiso R . . . . . . H421 H 0.0080 1.2176 0.6481 0.0971 1.0000 Uiso R . . . . . . H431 H -0.0318 1.3851 0.6923 0.1040 1.0000 Uiso R . . . . . . H441 H 0.0408 1.5358 0.6310 0.1053 1.0000 Uiso R . . . . . . H451 H 0.1516 1.5159 0.5227 0.1260 1.0000 Uiso R . . . . . . H461 H 0.1927 1.3500 0.4779 0.1035 1.0000 Uiso R . . . . . . H521 H -0.2566 0.7666 0.8173 0.2510 1.0000 Uiso R . . . . . . H522 H -0.2245 0.8520 0.7503 0.2511 1.0000 Uiso R . . . . . . H523 H -0.2100 0.7229 0.7293 0.2505 1.0000 Uiso R . . . . . . H531 H -0.0161 0.8896 0.9465 0.2680 1.0000 Uiso R . . . . . . H532 H -0.1409 0.9100 0.9102 0.2679 1.0000 Uiso R . . . . . . H533 H -0.1325 0.7907 0.9338 0.2679 1.0000 Uiso R . . . . . . H541 H -0.1190 0.6007 0.8412 0.2346 1.0000 Uiso R . . . . . . H542 H -0.1489 0.6032 0.7379 0.2348 1.0000 Uiso R . . . . . . H543 H -0.0339 0.5659 0.7770 0.2350 1.0000 Uiso R . . . . . . H551 H 0.0617 0.6832 0.9073 0.2433 1.0000 Uiso R . . . . . . H552 H 0.1026 0.8150 0.9018 0.2426 1.0000 Uiso R . . . . . . H553 H 0.1470 0.7205 0.8405 0.2433 1.0000 Uiso R . . . . . . H561 H 0.1108 0.7321 0.5884 0.0803 1.0000 Uiso R . . . . . . H562 H 0.1753 0.7693 0.5141 0.0793 1.0000 Uiso R . . . . . . H581 H 0.3845 0.9000 0.5662 0.1257 1.0000 Uiso R . . . . . . H591 H 0.5558 0.9091 0.6539 0.1810 1.0000 Uiso R . . . . . . H601 H 0.5624 0.8096 0.7643 0.1868 1.0000 Uiso R . . . . . . H611 H 0.3981 0.7043 0.7956 0.1506 1.0000 Uiso R . . . . . . H621 H 0.2228 0.6917 0.7083 0.1158 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 B16 0.0629(18) 0.076(2) 0.0653(18) 0.0125(16) 0.0141(14) 0.0119(15) B47 0.0621(17) 0.0543(16) 0.0715(18) 0.0164(14) 0.0135(14) 0.0182(13) O17 0.1248(19) 0.0890(14) 0.0611(12) 0.0163(11) 0.0079(12) 0.0001(13) O20 0.0956(15) 0.0805(14) 0.0731(13) 0.0054(10) 0.0117(11) 0.0197(11) O48 0.1143(17) 0.0626(11) 0.0951(14) 0.0261(10) 0.0498(13) 0.0336(11) O51 0.0953(14) 0.0588(11) 0.0826(12) 0.0214(9) 0.0319(11) 0.0278(10) N1 0.1007(19) 0.100(2) 0.0626(15) 0.0129(13) 0.0118(13) 0.0373(15) N3 0.0984(19) 0.0967(18) 0.0626(14) 0.0241(14) 0.0185(13) 0.0431(15) N9 0.0758(14) 0.0706(14) 0.0640(13) 0.0164(11) 0.0202(11) 0.0287(11) N32 0.0807(16) 0.0736(15) 0.0734(15) 0.0193(12) 0.0206(12) 0.0187(12) N34 0.0773(15) 0.0712(14) 0.0749(15) 0.0121(12) 0.0249(12) 0.0215(12) N40 0.0628(12) 0.0535(12) 0.0690(13) 0.0091(10) 0.0144(10) 0.0184(10) C2 0.109(3) 0.108(3) 0.0630(18) 0.0233(19) 0.0101(17) 0.041(2) C4 0.0662(16) 0.0777(18) 0.0605(16) 0.0186(14) 0.0181(12) 0.0293(14) C5 0.0572(15) 0.0731(16) 0.0588(15) 0.0143(13) 0.0144(12) 0.0194(12) C6 0.0605(15) 0.0777(18) 0.0663(17) 0.0133(14) 0.0154(12) 0.0200(13) C7 0.0654(16) 0.0700(17) 0.0619(15) 0.0170(13) 0.0097(12) 0.0187(13) C8 0.0654(16) 0.0706(17) 0.0616(15) 0.0162(13) 0.0155(12) 0.0172(13) C10 0.0620(16) 0.0750(18) 0.0842(19) 0.0082(15) 0.0202(14) 0.0181(14) C11 0.184(4) 0.099(3) 0.085(2) 0.019(2) 0.042(3) 0.074(3) C12 0.183(5) 0.102(3) 0.127(4) 0.034(3) 0.046(3) 0.074(3) C13 0.122(3) 0.076(2) 0.167(5) 0.013(3) 0.014(3) 0.026(2) C14 0.166(5) 0.086(3) 0.139(4) -0.027(3) -0.015(3) 0.037(3) C15 0.141(4) 0.087(2) 0.097(3) -0.012(2) -0.017(2) 0.031(2) C18 0.103(3) 0.113(3) 0.0544(17) 0.0082(17) 0.0074(16) -0.006(2) C19 0.099(2) 0.107(3) 0.0684(19) -0.0076(18) 0.0108(17) 0.020(2) C21 0.116(3) 0.150(4) 0.094(3) 0.022(3) -0.004(2) 0.032(3) C22 0.169(5) 0.196(5) 0.077(3) 0.029(3) 0.032(3) -0.031(4) C23 0.163(5) 0.113(3) 0.115(3) -0.011(3) -0.010(3) -0.001(3) C24 0.141(4) 0.257(7) 0.119(4) -0.024(4) 0.033(3) 0.095(5) C25 0.0862(19) 0.0687(17) 0.0813(18) 0.0230(14) 0.0268(16) 0.0275(15) C26 0.0833(19) 0.0687(17) 0.0659(16) 0.0213(13) 0.0193(14) 0.0317(15) C27 0.084(2) 0.0765(19) 0.0796(19) 0.0138(15) 0.0223(16) 0.0269(17) C28 0.082(2) 0.111(3) 0.091(2) 0.022(2) 0.0268(18) 0.0244(19) C29 0.102(3) 0.117(3) 0.098(2) 0.034(2) 0.038(2) 0.054(2) C30 0.135(3) 0.095(3) 0.117(3) 0.020(2) 0.045(3) 0.065(3) C31 0.111(3) 0.073(2) 0.102(2) 0.0171(18) 0.033(2) 0.0345(19) C33 0.082(2) 0.085(2) 0.0733(18) 0.0177(16) 0.0276(15) 0.0217(16) C35 0.0580(15) 0.0589(15) 0.0647(15) 0.0069(12) 0.0148(12) 0.0150(11) C36 0.0560(14) 0.0543(13) 0.0605(14) 0.0114(11) 0.0088(11) 0.0116(11) C37 0.0566(14) 0.0600(15) 0.0629(15) 0.0125(12) 0.0080(12) 0.0100(11) C38 0.0684(16) 0.0535(14) 0.0682(16) 0.0107(12) 0.0176(13) 0.0194(12) C39 0.0623(15) 0.0545(14) 0.0651(15) 0.0111(12) 0.0123(12) 0.0167(11) C41 0.0600(15) 0.0575(15) 0.0682(16) 0.0184(12) 0.0035(12) 0.0104(12) C42 0.102(2) 0.0593(16) 0.0817(19) 0.0236(14) 0.0285(17) 0.0236(15) C43 0.108(2) 0.0660(18) 0.089(2) 0.0176(16) 0.0263(18) 0.0310(17) C44 0.101(2) 0.0587(17) 0.106(2) 0.0211(16) 0.016(2) 0.0246(16) C45 0.112(3) 0.067(2) 0.133(3) 0.044(2) 0.036(2) 0.0277(19) C46 0.090(2) 0.0715(19) 0.103(2) 0.0352(17) 0.0331(18) 0.0222(16) C49 0.144(3) 0.084(2) 0.112(3) 0.045(2) 0.074(3) 0.050(2) C50 0.123(3) 0.0662(18) 0.096(2) 0.0361(16) 0.045(2) 0.0299(18) C52 0.107(4) 0.228(7) 0.272(8) 0.150(7) 0.067(5) 0.059(4) C53 0.357(11) 0.126(4) 0.161(5) 0.051(4) 0.166(7) 0.087(5) C54 0.267(8) 0.086(3) 0.227(7) 0.055(4) 0.158(6) 0.045(4) C55 0.166(5) 0.310(9) 0.153(5) 0.126(6) 0.035(4) 0.123(6) C56 0.0710(17) 0.0537(14) 0.0771(17) 0.0058(12) 0.0120(13) 0.0214(12) C57 0.0705(18) 0.0621(15) 0.0791(18) 0.0037(13) 0.0168(14) 0.0244(13) C58 0.069(2) 0.124(3) 0.123(3) 0.039(2) 0.024(2) 0.024(2) C59 0.067(3) 0.195(6) 0.192(5) 0.072(5) 0.027(3) 0.021(3) C60 0.094(3) 0.183(5) 0.188(6) 0.068(5) -0.009(3) 0.054(4) C61 0.098(3) 0.134(4) 0.153(4) 0.057(3) -0.002(3) 0.040(3) C62 0.085(2) 0.090(2) 0.119(3) 0.038(2) 0.014(2) 0.0302(18) _refine_ls_extinction_coef 46(11) _refine_ls_extinction_method 'Larson (1970), Equation 22' _oxford_refine_ls_scale 4.713(13) 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 B16 . O17 . 1.352(4) yes B16 . O20 . 1.346(4) yes B16 . C8 . 1.552(4) yes B47 . O48 . 1.348(4) yes B47 . O51 . 1.357(3) yes B47 . C39 . 1.548(4) yes O17 . C18 . 1.454(4) yes O20 . C19 . 1.457(4) yes O48 . C49 . 1.441(4) yes O51 . C50 . 1.445(4) yes N1 . C2 . 1.340(4) yes N1 . C6 . 1.350(4) yes N3 . C2 . 1.320(4) yes N3 . C4 . 1.324(4) yes N9 . C4 . 1.369(4) yes N9 . C8 . 1.387(3) yes N9 . C25 . 1.463(4) yes N32 . C33 . 1.338(4) yes N32 . C37 . 1.347(3) yes N34 . C33 . 1.318(4) yes N34 . C35 . 1.335(3) yes N40 . C35 . 1.360(3) yes N40 . C39 . 1.389(3) yes N40 . C56 . 1.460(3) yes C2 . H21 . 0.936 no C4 . C5 . 1.411(4) yes C5 . C6 . 1.394(4) yes C5 . C7 . 1.432(4) yes C6 . C10 . 1.485(4) yes C7 . C8 . 1.366(4) yes C7 . H71 . 0.942 no C10 . C11 . 1.367(5) yes C10 . C15 . 1.366(5) yes C11 . C12 . 1.390(6) yes C11 . H111 . 0.932 no C12 . C13 . 1.356(7) yes C12 . H121 . 0.944 no C13 . C14 . 1.354(7) yes C13 . H131 . 0.935 no C14 . C15 . 1.377(6) yes C14 . H141 . 0.942 no C15 . H151 . 0.933 no C18 . C19 . 1.529(6) yes C18 . C21 . 1.532(6) yes C18 . C22 . 1.512(5) yes C19 . C23 . 1.484(6) yes C19 . C24 . 1.534(6) yes C21 . H211 . 0.964 no C21 . H212 . 0.966 no C21 . H213 . 0.971 no C22 . H221 . 0.958 no C22 . H222 . 0.966 no C22 . H223 . 0.961 no C23 . H231 . 0.966 no C23 . H232 . 0.964 no C23 . H233 . 0.956 no C24 . H241 . 0.963 no C24 . H242 . 0.944 no C24 . H243 . 0.961 no C25 . C26 . 1.512(4) yes C25 . H251 . 0.974 no C25 . H252 . 0.975 no C26 . C27 . 1.365(4) yes C26 . C31 . 1.389(4) yes C27 . C28 . 1.384(5) yes C27 . H271 . 0.930 no C28 . C29 . 1.361(5) yes C28 . H281 . 0.953 no C29 . C30 . 1.362(6) yes C29 . H291 . 0.935 no C30 . C31 . 1.381(5) yes C30 . H301 . 0.934 no C31 . H311 . 0.938 no C33 . H331 . 0.949 no C35 . C36 . 1.412(4) yes C36 . C37 . 1.404(4) yes C36 . C38 . 1.428(4) yes C37 . C41 . 1.477(4) yes C38 . C39 . 1.373(4) yes C38 . H381 . 0.946 no C41 . C42 . 1.385(4) yes C41 . C46 . 1.389(4) yes C42 . C43 . 1.379(4) yes C42 . H421 . 0.931 no C43 . C44 . 1.349(4) yes C43 . H431 . 0.944 no C44 . C45 . 1.374(5) yes C44 . H441 . 0.937 no C45 . C46 . 1.374(5) yes C45 . H451 . 0.928 no C46 . H461 . 0.938 no C49 . C50 . 1.488(5) yes C49 . C52 . 1.632(8) yes C49 . C53 . 1.394(6) yes C50 . C54 . 1.424(6) yes C50 . C55 . 1.578(7) yes C52 . H521 . 0.983 no C52 . H522 . 0.991 no C52 . H523 . 1.004 no C53 . H531 . 0.981 no C53 . H532 . 0.978 no C53 . H533 . 0.982 no C54 . H541 . 0.977 no C54 . H542 . 0.991 no C54 . H543 . 0.972 no C55 . H551 . 0.973 no C55 . H552 . 1.011 no C55 . H553 . 0.977 no C56 . C57 . 1.498(4) yes C56 . H561 . 0.964 no C56 . H562 . 0.966 no C57 . C58 . 1.376(5) yes C57 . C62 . 1.383(5) yes C58 . C59 . 1.378(6) yes C58 . H581 . 0.945 no C59 . C60 . 1.360(7) yes C59 . H591 . 0.927 no C60 . C61 . 1.342(7) yes C60 . H601 . 0.929 no C61 . C62 . 1.365(6) yes C61 . H611 . 0.949 no C62 . H621 . 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 O17 . B16 . O20 . 114.0(3) yes O17 . B16 . C8 . 120.9(3) yes O20 . B16 . C8 . 125.1(3) yes O48 . B47 . O51 . 113.6(2) yes O48 . B47 . C39 . 120.5(2) yes O51 . B47 . C39 . 125.8(2) yes B16 . O17 . C18 . 106.8(3) yes B16 . O20 . C19 . 107.2(3) yes B47 . O48 . C49 . 107.1(2) yes B47 . O51 . C50 . 107.1(2) yes C2 . N1 . C6 . 117.8(3) yes C2 . N3 . C4 . 112.4(3) yes C4 . N9 . C8 . 108.4(2) yes C4 . N9 . C25 . 125.0(2) yes C8 . N9 . C25 . 126.3(2) yes C33 . N32 . C37 . 117.4(2) yes C33 . N34 . C35 . 111.6(2) yes C35 . N40 . C39 . 108.7(2) yes C35 . N40 . C56 . 124.9(2) yes C39 . N40 . C56 . 126.2(2) yes N1 . C2 . N3 . 128.8(3) yes N1 . C2 . H21 . 114.6 no N3 . C2 . H21 . 116.6 no N9 . C4 . N3 . 124.8(3) yes N9 . C4 . C5 . 109.2(2) yes N3 . C4 . C5 . 125.9(3) yes C4 . C5 . C6 . 115.9(2) yes C4 . C5 . C7 . 105.1(2) yes C6 . C5 . C7 . 139.0(3) yes C5 . C6 . N1 . 119.2(3) yes C5 . C6 . C10 . 125.6(3) yes N1 . C6 . C10 . 115.2(3) yes C5 . C7 . C8 . 108.6(2) yes C5 . C7 . H71 . 127.8 no C8 . C7 . H71 . 123.6 no B16 . C8 . N9 . 124.9(2) yes B16 . C8 . C7 . 126.5(3) yes N9 . C8 . C7 . 108.7(2) yes C6 . C10 . C11 . 122.7(3) yes C6 . C10 . C15 . 120.2(3) yes C11 . C10 . C15 . 117.1(3) yes C10 . C11 . C12 . 121.7(4) yes C10 . C11 . H111 . 118.5 no C12 . C11 . H111 . 119.8 no C11 . C12 . C13 . 119.6(4) yes C11 . C12 . H121 . 121.5 no C13 . C12 . H121 . 118.9 no C12 . C13 . C14 . 119.6(4) yes C12 . C13 . H131 . 120.3 no C14 . C13 . H131 . 120.1 no C13 . C14 . C15 . 120.3(4) yes C13 . C14 . H141 . 119.9 no C15 . C14 . H141 . 119.8 no C14 . C15 . C10 . 121.6(4) yes C14 . C15 . H151 . 120.2 no C10 . C15 . H151 . 118.2 no O17 . C18 . C19 . 103.4(3) yes O17 . C18 . C21 . 105.1(3) yes C19 . C18 . C21 . 112.9(3) yes O17 . C18 . C22 . 107.8(3) yes C19 . C18 . C22 . 115.8(4) yes C21 . C18 . C22 . 110.8(4) yes C18 . C19 . O20 . 102.6(3) yes C18 . C19 . C23 . 115.1(4) yes O20 . C19 . C23 . 110.1(3) yes C18 . C19 . C24 . 112.2(4) yes O20 . C19 . C24 . 104.0(3) yes C23 . C19 . C24 . 111.8(4) yes C18 . C21 . H211 . 108.5 no C18 . C21 . H212 . 109.9 no H211 . C21 . H212 . 109.2 no C18 . C21 . H213 . 109.7 no H211 . C21 . H213 . 109.2 no H212 . C21 . H213 . 110.3 no C18 . C22 . H221 . 108.7 no C18 . C22 . H222 . 109.0 no H221 . C22 . H222 . 110.8 no C18 . C22 . H223 . 108.4 no H221 . C22 . H223 . 109.7 no H222 . C22 . H223 . 110.2 no C19 . C23 . H231 . 107.3 no C19 . C23 . H232 . 110.8 no H231 . C23 . H232 . 110.7 no C19 . C23 . H233 . 107.9 no H231 . C23 . H233 . 109.4 no H232 . C23 . H233 . 110.6 no C19 . C24 . H241 . 109.5 no C19 . C24 . H242 . 109.5 no H241 . C24 . H242 . 110.4 no C19 . C24 . H243 . 109.1 no H241 . C24 . H243 . 109.0 no H242 . C24 . H243 . 109.3 no N9 . C25 . C26 . 113.5(2) yes N9 . C25 . H251 . 106.4 no C26 . C25 . H251 . 108.0 no N9 . C25 . H252 . 109.1 no C26 . C25 . H252 . 108.3 no H251 . C25 . H252 . 111.5 no C25 . C26 . C27 . 123.4(3) yes C25 . C26 . C31 . 119.0(3) yes C27 . C26 . C31 . 117.6(3) yes C26 . C27 . C28 . 121.3(3) yes C26 . C27 . H271 . 119.5 no C28 . C27 . H271 . 119.1 no C27 . C28 . C29 . 120.5(4) yes C27 . C28 . H281 . 119.6 no C29 . C28 . H281 . 119.9 no C28 . C29 . C30 . 119.2(3) yes C28 . C29 . H291 . 121.3 no C30 . C29 . H291 . 119.5 no C29 . C30 . C31 . 120.6(3) yes C29 . C30 . H301 . 119.7 no C31 . C30 . H301 . 119.6 no C26 . C31 . C30 . 120.7(4) yes C26 . C31 . H311 . 118.8 no C30 . C31 . H311 . 120.5 no N32 . C33 . N34 . 130.0(3) yes N32 . C33 . H331 . 115.9 no N34 . C33 . H331 . 114.1 no N40 . C35 . N34 . 124.7(2) yes N40 . C35 . C36 . 109.3(2) yes N34 . C35 . C36 . 126.0(2) yes C35 . C36 . C37 . 115.7(2) yes C35 . C36 . C38 . 105.2(2) yes C37 . C36 . C38 . 139.1(2) yes C36 . C37 . N32 . 119.3(2) yes C36 . C37 . C41 . 124.8(2) yes N32 . C37 . C41 . 115.9(2) yes C36 . C38 . C39 . 108.4(2) yes C36 . C38 . H381 . 127.5 no C39 . C38 . H381 . 124.0 no B47 . C39 . N40 . 127.1(2) yes B47 . C39 . C38 . 124.3(2) yes N40 . C39 . C38 . 108.3(2) yes C37 . C41 . C42 . 122.9(2) yes C37 . C41 . C46 . 120.3(3) yes C42 . C41 . C46 . 116.9(3) yes C41 . C42 . C43 . 121.6(3) yes C41 . C42 . H421 . 119.7 no C43 . C42 . H421 . 118.6 no C42 . C43 . C44 . 120.6(3) yes C42 . C43 . H431 . 119.6 no C44 . C43 . H431 . 119.9 no C43 . C44 . C45 . 119.3(3) yes C43 . C44 . H441 . 120.5 no C45 . C44 . H441 . 120.2 no C44 . C45 . C46 . 120.7(3) yes C44 . C45 . H451 . 120.2 no C46 . C45 . H451 . 119.1 no C41 . C46 . C45 . 121.0(3) yes C41 . C46 . H461 . 119.9 no C45 . C46 . H461 . 119.1 no O48 . C49 . C50 . 105.2(2) yes O48 . C49 . C52 . 100.9(3) yes C50 . C49 . C52 . 104.7(4) yes O48 . C49 . C53 . 116.0(4) yes C50 . C49 . C53 . 126.9(4) yes C52 . C49 . C53 . 99.1(5) yes C49 . C50 . O51 . 104.7(2) yes C49 . C50 . C54 . 124.7(4) yes O51 . C50 . C54 . 114.2(4) yes C49 . C50 . C55 . 105.8(4) yes O51 . C50 . C55 . 102.7(3) yes C54 . C50 . C55 . 102.4(5) yes C49 . C52 . H521 . 106.9 no C49 . C52 . H522 . 111.4 no H521 . C52 . H522 . 111.3 no C49 . C52 . H523 . 104.6 no H521 . C52 . H523 . 109.8 no H522 . C52 . H523 . 112.6 no C49 . C53 . H531 . 104.2 no C49 . C53 . H532 . 109.4 no H531 . C53 . H532 . 112.3 no C49 . C53 . H533 . 109.0 no H531 . C53 . H533 . 110.5 no H532 . C53 . H533 . 111.2 no C50 . C54 . H541 . 109.2 no C50 . C54 . H542 . 102.6 no H541 . C54 . H542 . 111.0 no C50 . C54 . H543 . 109.1 no H541 . C54 . H543 . 111.6 no H542 . C54 . H543 . 112.9 no C50 . C55 . H551 . 108.5 no C50 . C55 . H552 . 104.4 no H551 . C55 . H552 . 110.7 no C50 . C55 . H553 . 110.3 no H551 . C55 . H553 . 110.9 no H552 . C55 . H553 . 111.8 no N40 . C56 . C57 . 113.0(2) yes N40 . C56 . H561 . 108.2 no C57 . C56 . H561 . 109.8 no N40 . C56 . H562 . 109.4 no C57 . C56 . H562 . 109.1 no H561 . C56 . H562 . 107.2 no C56 . C57 . C58 . 119.9(3) yes C56 . C57 . C62 . 121.8(3) yes C58 . C57 . C62 . 118.2(3) yes C57 . C58 . C59 . 118.6(4) yes C57 . C58 . H581 . 121.3 no C59 . C58 . H581 . 120.0 no C58 . C59 . C60 . 121.4(5) yes C58 . C59 . H591 . 118.8 no C60 . C59 . H591 . 119.8 no C59 . C60 . C61 . 120.8(4) yes C59 . C60 . H601 . 120.1 no C61 . C60 . H601 . 119.1 no C60 . C61 . C62 . 118.6(5) yes C60 . C61 . H611 . 120.1 no C62 . C61 . H611 . 121.3 no C57 . C62 . C61 . 122.3(4) yes C57 . C62 . H621 . 118.2 no C61 . C62 . H621 . 119.5 no loop_ _geom_hbond_atom_site_label_D _geom_hbond_site_symmetry_D _geom_hbond_atom_site_label_H _geom_hbond_site_symmetry_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_angle_DHA _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_publ_flag C11 . H111 . C7 . 132 0.93 2.53 3.226(6) yes C42 . H421 . C38 . 127 0.93 2.57 3.225(6) yes C56 . H561 . O51 . 123 0.96 2.48 3.117(6) yes _chemical_name_common ;(7-benzyl-4-phenyl-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan- 2-yl)-7H-pyrrolo(2 ; data_2 _database_code_depnum_ccdc_archive 'CCDC 703632' _audit_creation_date 08-09-25 _audit_creation_method CRYSTALS_ver_12.86 _chemical_name_systematic (7-benzyl-4-phenyl-6-p-tolyl-7H-pyrrolo[2,3-d]pyrimidine) _chemical_formula_moiety 'C26 H21 N3' # Given Formula = C26 H21 N3 # Dc = 1.25 Fooo = 396.00 Mu = 5.77 M = 375.47 # Found Formula = C26 H21 N3 # Dc = 1.25 FOOO = 396.00 Mu = 5.77 M = 375.47 _chemical_formula_sum 'C26 H21 N3' _exptl_crystal_description prism _exptl_crystal_colour colourless _diffrn_ambient_temperature 298 _cell_length_a 9.8513(18) _cell_length_b 10.4417(18) _cell_length_c 11.565(2) _cell_angle_alpha 101.076(14) _cell_angle_beta 114.026(17) _cell_angle_gamma 104.117(15) _cell_volume 995.1(4) _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_int_tables_number 2 # 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 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' _cell_formula_units_Z 2 _chemical_formula_weight 375.47 _cell_measurement_reflns_used 7082 _cell_measurement_theta_min 4 _cell_measurement_theta_max 78 _cell_measurement_temperature 298 _exptl_crystal_size_min 0.22 _exptl_crystal_size_mid 0.27 _exptl_crystal_size_max 0.49 _exptl_crystal_density_diffrn 1.253 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' # Non-dispersive F(000): _exptl_crystal_F_000 396 _exptl_absorpt_coefficient_mu 0.577 # Sheldrick geometric approximatio 0.86 0.88 _exptl_absorpt_correction_type analytical _exptl_absorpt_process_details ; Analytical Absorption (De Meulenaer & Tompa, 1965) ; _exptl_absorpt_correction_T_min 0.86 _exptl_absorpt_correction_T_max 0.88 _diffrn_measurement_device 'Oxford Diffraction XCALIBUR' _diffrn_measurement_device_type Area _diffrn_radiation_monochromator graphite _diffrn_radiation_probe ? _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 RED, (Oxford Diffraction, 2002)' _computing_data_reduction 'CrysAlis RED, (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 31243 _reflns_number_total 4195 _diffrn_reflns_av_R_equivalents 0.065 # Number of reflections with Friedels Law is 4195 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 4229 _diffrn_reflns_theta_min 4.433 _diffrn_reflns_theta_max 78.773 _diffrn_measured_fraction_theta_max 0.977 _diffrn_reflns_theta_full 73.259 _diffrn_measured_fraction_theta_full 0.997 _diffrn_reflns_limit_h_min -12 _diffrn_reflns_limit_h_max 12 _diffrn_reflns_limit_k_min -13 _diffrn_reflns_limit_k_max 13 _diffrn_reflns_limit_l_min -14 _diffrn_reflns_limit_l_max 14 _reflns_limit_h_min -12 _reflns_limit_h_max 11 _reflns_limit_k_min -13 _reflns_limit_k_max 13 _reflns_limit_l_min 0 _reflns_limit_l_max 14 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.15 _refine_diff_density_max 0.14 # The current dictionary definitions do not cover the # situation where the reflections used for refinement were # selected by a user-defined sigma threshold # The values actually used during refinement _oxford_reflns_threshold_expression_ref I>2.0\s(I) _refine_ls_number_reflns 2354 _refine_ls_number_restraints 0 _refine_ls_number_parameters 263 _oxford_refine_ls_R_factor_ref 0.0501 _refine_ls_wR_factor_ref 0.0610 _refine_ls_goodness_of_fit_ref 1.0007 _refine_ls_shift/su_max 0.000253 # The values computed from all data _oxford_reflns_number_all 4179 _refine_ls_R_factor_all 0.0791 _refine_ls_wR_factor_all 0.0769 # The values computed with a 2 sigma cutoff - a la SHELX _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 2354 _refine_ls_R_factor_gt 0.0501 _refine_ls_wR_factor_gt 0.0610 _refine_ls_structure_factor_coef F _refine_ls_matrix_type full _refine_ls_hydrogen_treatment constr # none, undef, noref, refall, # refxyz, refU, constr or mixed _refine_ls_weighting_scheme calc _refine_ls_weighting_details ; Method, part 1, Chebychev polynomial, (Watkin, 1994, Prince, 1982) [weight] = 1.0/[A~0~*T~0~(x)+A~1~*T~1~(x) ... +A~n-1~]*T~n-1~(x)] where A~i~ are the Chebychev coefficients listed below and x= Fcalc/Fmax Method = Robust Weighting (Prince, 1982) W = [weight] * [1-(deltaF/6*sigmaF)^2^]^2^ A~i~ are: 9.84 1.91 7.31 ; # Insert your own references if required - in alphabetical order loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _oxford_atom_site_special_shape _atom_site_attached_hydrogens C11 C 1.1384(3) 1.1026(3) 0.3462(3) 0.0681 1.0000 Uani . . . . . . . C12 C 1.2754(3) 1.1505(3) 0.3360(3) 0.0773 1.0000 Uani . . . . . . . C13 C 1.3417(3) 1.2890(3) 0.3539(3) 0.0728 1.0000 Uani . . . . . . . C14 C 1.2720(3) 1.3794(3) 0.3840(3) 0.0765 1.0000 Uani . . . . . . . C15 C 1.1345(3) 1.3323(3) 0.3938(3) 0.0676 1.0000 Uani . . . . . . . N1 N 0.8753(2) 1.24672(19) 0.4356(2) 0.0587 1.0000 Uani . . . . . . . N3 N 0.6390(2) 1.0833(2) 0.4117(2) 0.0598 1.0000 Uani . . . . . . . N9 N 0.5963(2) 0.84362(18) 0.31841(18) 0.0516 1.0000 Uani . . . . . . . C2 C 0.7419(3) 1.2107(3) 0.4458(3) 0.0628 1.0000 Uani . . . . . . . C4 C 0.6815(2) 0.9838(2) 0.3617(2) 0.0501 1.0000 Uani . . . . . . . C5 C 0.8187(2) 1.0046(2) 0.3444(2) 0.0495 1.0000 Uani . . . . . . . C6 C 0.9168(2) 1.1444(2) 0.3844(2) 0.0507 1.0000 Uani . . . . . . . C7 C 0.8116(3) 0.8667(2) 0.2883(2) 0.0553 1.0000 Uani . . . . . . . C8 C 0.6778(2) 0.7715(2) 0.2741(2) 0.0516 1.0000 Uani . . . . . . . C10 C 1.0642(2) 1.1923(2) 0.3738(2) 0.0514 1.0000 Uani . . . . . . . C16 C 0.6267(2) 0.6194(2) 0.2259(2) 0.0520 1.0000 Uani . . . . . . . C17 C 0.7419(3) 0.5583(3) 0.2613(2) 0.0617 1.0000 Uani . . . . . . . C18 C 0.6996(3) 0.4147(3) 0.2150(3) 0.0673 1.0000 Uani . . . . . . . C19 C 0.5429(3) 0.3272(2) 0.1331(3) 0.0612 1.0000 Uani . . . . . . . C20 C 0.4289(3) 0.3880(2) 0.0961(2) 0.0611 1.0000 Uani . . . . . . . C21 C 0.4683(3) 0.5312(2) 0.1406(2) 0.0580 1.0000 Uani . . . . . . . C22 C 0.4950(4) 0.1710(3) 0.0864(3) 0.0837 1.0000 Uani . . . . . . . C23 C 0.4536(3) 0.7876(2) 0.3309(2) 0.0555 1.0000 Uani . . . . . . . C24 C 0.2994(2) 0.7670(2) 0.2116(2) 0.0553 1.0000 Uani . . . . . . . C25 C 0.2941(3) 0.8301(3) 0.1169(3) 0.0761 1.0000 Uani . . . . . . . C26 C 0.1506(4) 0.8121(4) 0.0105(3) 0.0956 1.0000 Uani . . . . . . . C27 C 0.0111(4) 0.7303(4) -0.0022(3) 0.0980 1.0000 Uani . . . . . . . C28 C 0.0152(4) 0.6674(4) 0.0922(4) 0.1064 1.0000 Uani . . . . . . . C29 C 0.1577(3) 0.6845(3) 0.1978(3) 0.0823 1.0000 Uani . . . . . . . H21 H 0.7139 1.2877 0.4817 0.0739 1.0000 Uiso R . . . . . . H71 H 0.8854 0.8431 0.2651 0.0678 1.0000 Uiso R . . . . . . H151 H 1.0860 1.3945 0.4144 0.0802 1.0000 Uiso R . . . . . . H141 H 1.3183 1.4776 0.3982 0.0926 1.0000 Uiso R . . . . . . H131 H 1.4367 1.3219 0.3453 0.0871 1.0000 Uiso R . . . . . . H121 H 1.3205 1.0856 0.3172 0.0953 1.0000 Uiso R . . . . . . H111 H 1.0951 1.0069 0.3348 0.0821 1.0000 Uiso R . . . . . . H171 H 0.8519 0.6180 0.3197 0.0708 1.0000 Uiso R . . . . . . H181 H 0.7814 0.3740 0.2428 0.0797 1.0000 Uiso R . . . . . . H201 H 0.3215 0.3309 0.0384 0.0715 1.0000 Uiso R . . . . . . H211 H 0.3860 0.5715 0.1102 0.0674 1.0000 Uiso R . . . . . . H223 H 0.4317 0.1308 -0.0101 0.1277 1.0000 Uiso R . . . . . . H221 H 0.5901 0.1475 0.1118 0.1269 1.0000 Uiso R . . . . . . H222 H 0.4364 0.1278 0.1271 0.1274 1.0000 Uiso R . . . . . . H231 H 0.4648 0.8522 0.4114 0.0669 1.0000 Uiso R . . . . . . H232 H 0.4496 0.6968 0.3449 0.0666 1.0000 Uiso R . . . . . . H251 H 0.3911 0.8864 0.1243 0.0887 1.0000 Uiso R . . . . . . H261 H 0.1514 0.8582 -0.0526 0.1144 1.0000 Uiso R . . . . . . H271 H -0.0875 0.7156 -0.0740 0.1113 1.0000 Uiso R . . . . . . H281 H -0.0823 0.6128 0.0844 0.1196 1.0000 Uiso R . . . . . . H291 H 0.1593 0.6380 0.2614 0.0962 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 C11 0.0533(13) 0.0608(15) 0.0898(18) 0.0202(13) 0.0377(13) 0.0171(11) C12 0.0600(15) 0.0802(19) 0.096(2) 0.0209(16) 0.0450(15) 0.0253(14) C13 0.0527(13) 0.092(2) 0.0726(16) 0.0305(14) 0.0329(12) 0.0169(13) C14 0.0605(15) 0.0701(17) 0.099(2) 0.0335(15) 0.0427(15) 0.0116(13) C15 0.0563(14) 0.0595(15) 0.0843(18) 0.0215(13) 0.0352(13) 0.0150(11) N1 0.0503(10) 0.0530(11) 0.0686(12) 0.0119(9) 0.0289(9) 0.0172(9) N3 0.0514(10) 0.0583(12) 0.0703(12) 0.0140(10) 0.0328(10) 0.0194(9) N9 0.0440(9) 0.0509(10) 0.0591(10) 0.0144(8) 0.0279(8) 0.0130(8) C2 0.0567(13) 0.0576(14) 0.0738(16) 0.0132(12) 0.0344(12) 0.0208(12) C4 0.0438(10) 0.0522(12) 0.0530(12) 0.0136(10) 0.0242(9) 0.0162(9) C5 0.0438(10) 0.0520(12) 0.0513(12) 0.0154(10) 0.0223(9) 0.0166(9) C6 0.0443(11) 0.0550(12) 0.0502(11) 0.0156(10) 0.0207(9) 0.0182(10) C7 0.0495(12) 0.0567(13) 0.0640(13) 0.0168(11) 0.0313(10) 0.0209(10) C8 0.0467(11) 0.0519(12) 0.0548(12) 0.0155(10) 0.0241(10) 0.0170(10) C10 0.0420(11) 0.0558(13) 0.0517(12) 0.0166(10) 0.0204(9) 0.0147(10) C16 0.0489(12) 0.0495(12) 0.0561(12) 0.0169(10) 0.0253(10) 0.0152(10) C17 0.0519(13) 0.0591(14) 0.0656(14) 0.0187(12) 0.0222(11) 0.0184(11) C18 0.0659(15) 0.0572(15) 0.0752(16) 0.0228(12) 0.0278(13) 0.0262(12) C19 0.0717(15) 0.0523(13) 0.0659(14) 0.0212(11) 0.0387(12) 0.0209(12) C20 0.0567(13) 0.0536(14) 0.0668(14) 0.0141(11) 0.0315(12) 0.0106(11) C21 0.0509(12) 0.0546(13) 0.0657(14) 0.0163(11) 0.0275(11) 0.0176(10) C22 0.102(2) 0.0567(16) 0.094(2) 0.0238(15) 0.0505(18) 0.0269(15) C23 0.0461(11) 0.0602(13) 0.0610(13) 0.0192(11) 0.0295(10) 0.0140(10) C24 0.0456(12) 0.0566(13) 0.0619(13) 0.0147(11) 0.0278(10) 0.0149(10) C25 0.0587(15) 0.0867(19) 0.0774(18) 0.0357(15) 0.0292(13) 0.0163(13) C26 0.076(2) 0.127(3) 0.083(2) 0.052(2) 0.0283(16) 0.0365(19) C27 0.0551(16) 0.142(3) 0.082(2) 0.033(2) 0.0216(15) 0.0322(18) C28 0.0511(16) 0.152(3) 0.096(2) 0.041(2) 0.0297(16) 0.0125(19) C29 0.0520(14) 0.107(2) 0.0805(18) 0.0371(17) 0.0314(13) 0.0120(14) _refine_ls_extinction_coef 72(5) _refine_ls_extinction_method 'Larson (1970), Equation 22' _oxford_refine_ls_scale 8.80(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 C11 . C12 . 1.382(3) yes C11 . C10 . 1.386(3) yes C11 . H111 . 0.945 no C12 . C13 . 1.369(4) yes C12 . H121 . 0.934 no C13 . C14 . 1.367(4) yes C13 . H131 . 0.968 no C14 . C15 . 1.383(3) yes C14 . H141 . 0.965 no C15 . C10 . 1.384(3) yes C15 . H151 . 0.945 no N1 . C2 . 1.336(3) yes N1 . C6 . 1.351(3) yes N3 . C2 . 1.329(3) yes N3 . C4 . 1.331(3) yes N9 . C4 . 1.369(3) yes N9 . C8 . 1.398(3) yes N9 . C23 . 1.462(3) yes C2 . H21 . 0.984 no C4 . C5 . 1.417(3) yes C5 . C6 . 1.403(3) yes C5 . C7 . 1.433(3) yes C6 . C10 . 1.479(3) yes C7 . C8 . 1.369(3) yes C7 . H71 . 0.939 no C8 . C16 . 1.459(3) yes C16 . C17 . 1.393(3) yes C16 . C21 . 1.397(3) yes C17 . C18 . 1.383(4) yes C17 . H171 . 0.966 no C18 . C19 . 1.380(4) yes C18 . H181 . 0.970 no C19 . C20 . 1.381(3) yes C19 . C22 . 1.501(4) yes C20 . C21 . 1.383(3) yes C20 . H201 . 0.941 no C21 . H211 . 0.974 no C22 . H223 . 0.968 no C22 . H221 . 0.969 no C22 . H222 . 0.967 no C23 . C24 . 1.510(3) yes C23 . H231 . 0.986 no C23 . H232 . 0.986 no C24 . C25 . 1.371(3) yes C24 . C29 . 1.377(3) yes C25 . C26 . 1.383(4) yes C25 . H251 . 0.952 no C26 . C27 . 1.362(4) yes C26 . H261 . 0.950 no C27 . C28 . 1.370(5) yes C27 . H271 . 0.938 no C28 . C29 . 1.376(4) yes C28 . H281 . 0.947 no C29 . H291 . 0.953 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 C12 . C11 . C10 . 121.3(2) yes C12 . C11 . H111 . 119.2 no C10 . C11 . H111 . 119.5 no C11 . C12 . C13 . 120.3(3) yes C11 . C12 . H121 . 117.8 no C13 . C12 . H121 . 121.9 no C12 . C13 . C14 . 119.2(2) yes C12 . C13 . H131 . 120.1 no C14 . C13 . H131 . 120.7 no C13 . C14 . C15 . 120.9(2) yes C13 . C14 . H141 . 120.1 no C15 . C14 . H141 . 119.0 no C14 . C15 . C10 . 120.8(2) yes C14 . C15 . H151 . 121.0 no C10 . C15 . H151 . 118.2 no C2 . N1 . C6 . 118.6(2) yes C2 . N3 . C4 . 112.10(18) yes C4 . N9 . C8 . 107.92(16) yes C4 . N9 . C23 . 122.99(18) yes C8 . N9 . C23 . 128.88(18) yes N1 . C2 . N3 . 128.6(2) yes N1 . C2 . H21 . 116.6 no N3 . C2 . H21 . 114.9 no N9 . C4 . N3 . 124.08(18) yes N9 . C4 . C5 . 109.71(18) yes N3 . C4 . C5 . 126.2(2) yes C4 . C5 . C6 . 115.6(2) yes C4 . C5 . C7 . 104.92(18) yes C6 . C5 . C7 . 139.4(2) yes C5 . C6 . N1 . 118.87(19) yes C5 . C6 . C10 . 125.59(19) yes N1 . C6 . C10 . 115.54(19) yes C5 . C7 . C8 . 108.68(18) yes C5 . C7 . H71 . 126.9 no C8 . C7 . H71 . 124.4 no N9 . C8 . C7 . 108.77(18) yes N9 . C8 . C16 . 123.83(18) yes C7 . C8 . C16 . 127.37(19) yes C6 . C10 . C11 . 122.7(2) yes C6 . C10 . C15 . 119.8(2) yes C11 . C10 . C15 . 117.5(2) yes C8 . C16 . C17 . 118.6(2) yes C8 . C16 . C21 . 123.5(2) yes C17 . C16 . C21 . 117.8(2) yes C16 . C17 . C18 . 120.7(2) yes C16 . C17 . H171 . 118.7 no C18 . C17 . H171 . 120.6 no C17 . C18 . C19 . 121.6(2) yes C17 . C18 . H181 . 119.5 no C19 . C18 . H181 . 118.9 no C18 . C19 . C20 . 117.7(2) yes C18 . C19 . C22 . 122.0(2) yes C20 . C19 . C22 . 120.3(2) yes C19 . C20 . C21 . 121.8(2) yes C19 . C20 . H201 . 119.5 no C21 . C20 . H201 . 118.7 no C16 . C21 . C20 . 120.3(2) yes C16 . C21 . H211 . 119.5 no C20 . C21 . H211 . 120.1 no C19 . C22 . H223 . 111.8 no C19 . C22 . H221 . 109.0 no H223 . C22 . H221 . 107.3 no C19 . C22 . H222 . 111.7 no H223 . C22 . H222 . 109.1 no H221 . C22 . H222 . 107.8 no N9 . C23 . C24 . 114.70(18) yes N9 . C23 . H231 . 108.0 no C24 . C23 . H231 . 109.0 no N9 . C23 . H232 . 107.9 no C24 . C23 . H232 . 108.8 no H231 . C23 . H232 . 108.3 no C23 . C24 . C25 . 122.5(2) yes C23 . C24 . C29 . 119.2(2) yes C25 . C24 . C29 . 118.3(2) yes C24 . C25 . C26 . 121.2(3) yes C24 . C25 . H251 . 119.2 no C26 . C25 . H251 . 119.6 no C25 . C26 . C27 . 120.1(3) yes C25 . C26 . H261 . 118.9 no C27 . C26 . H261 . 121.0 no C26 . C27 . C28 . 119.1(3) yes C26 . C27 . H271 . 121.7 no C28 . C27 . H271 . 119.2 no C27 . C28 . C29 . 120.9(3) yes C27 . C28 . H281 . 118.8 no C29 . C28 . H281 . 120.3 no C24 . C29 . C28 . 120.4(3) yes C24 . C29 . H291 . 119.4 no C28 . C29 . H291 . 120.2 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 C11 . H111 . C7 . 128 0.95 2.59 3.259(4) yes _chemical_name_common (7-benzyl-4-phenyl-6-p-tolyl-7H-pyrrolo(2,3-d)pyrimidine)