data_global _journal_name_full Org.Biomol.Chem. _journal_coden_Cambridge 0177 _publ_contact_author_name 'Roland Barret' _publ_contact_author_address ; Laboratoire de Chimie Therapeutique Universite de Lyon Universite Lyon 1 ISPB, INSERM U863, IFR 62 8 avenue Rockefeller LYON F-69373 Lyon cedex 08 FRANCE ; _publ_contact_author_email ROLAND.BARRET@SANTE.UNIV-LYON1.FR _publ_section_title ; Solvent-dependent oxidations of 5- and 6-azaindoles to trioxopyrrolopyridines and functionalised azaindoles ; _journal_coden_ASTM ? _journal_coeditor_code ? _journal_coeditor_name ? _journal_coeditor_notes ? _journal_date_accepted ? _journal_date_from_coeditor ? _journal_date_printers_final ? _journal_date_printers_first ? _journal_date_proofs_in ? _journal_date_proofs_out ? # PROCESSING SUMMARY (IUCr Office Use Only): _journal_date_recd_electronic ? _journal_date_to_coeditor ? _journal_issue ? _journal_page_first ? _journal_page_last ? _journal_suppl_publ_number ? _journal_suppl_publ_pages ? _journal_techeditor_code ? _journal_techeditor_notes ? _journal_volume ? _journal_year ? loop_ _publ_author_footnote ; ? # Footnote for author 1 ; ; ? # Footnote 2 ; # Check this file using the IUCr facility at: # http://checkcif.iucr.org/ # The content below is held in the file 'script/refcif.dat'. This is a text # file which you may edit to reflect local conditions. # Items which need looking at are represented by a '?'. # Items for which there are choices are prefixed with 'choose from'. _publ_contact_letter ; Please consider this CIF submission for publication as a Short Format Paper in Acta Crystallographica E. The figures will be sent by e-mail. ; _publ_requested_category EO # choose from: FI FM FO CI CM CO AD _publ_requested_coeditor_name 'Prof William Clegg' loop_ _publ_author_name 'Roland Barret' 'Sylvie Goncalves' 'Thierry Lomberget' 'Zahia Mahiout' data_1 _database_code_depnum_ccdc_archive 'CCDC 641655' _audit_creation_date 06-11-23 _audit_creation_method CRYSTALS_ver_12.84 _oxford_structure_analysis_title 'scale in P -1' _chemical_name_systematic ? _chemical_melting_point ? _cell_length_a 5.35 _cell_length_b 8.79 _cell_length_c 10.58 _cell_angle_alpha 111.47 _cell_angle_beta 94.77 _cell_angle_gamma 94.31 _cell_volume 458.77634(2) _symmetry_cell_setting triclinic _symmetry_space_group_name_H-M 'P -1' _symmetry_int_tables_number 2 _symmetry_space_group_name_Hall '- P1' 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' 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' 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' _cell_formula_units_Z 2 # Given Formula = C12 H24 N3 O4 # Dc = 1.99 Fooo = 228.00 Mu = 1.49 M = 274.34 # Found Formula = C9 H6 N2 O5 # Dc = 1.61 FOOO = 228.00 Mu = 1.35 M = 222.16 _chemical_formula_sum 'C9 H6 N2 O5' _chemical_formula_moiety 'C9 H6 N2 O5' _chemical_compound_source ? _chemical_formula_weight 222.16 _cell_measurement_reflns_used 0 _cell_measurement_theta_min 0 _cell_measurement_theta_max 0 _cell_measurement_temperature 293 _exptl_crystal_description needle _exptl_crystal_colour colorless _exptl_crystal_size_min 0.06 _exptl_crystal_size_mid 0.07 _exptl_crystal_size_max 0.21 _exptl_crystal_density_diffrn 1.608 _exptl_crystal_density_meas ? # Non-dispersive F(000): _exptl_crystal_F_000 228 _exptl_absorpt_coefficient_mu 0.135 # Sheldrick geometric approximatio 0.99 0.99 _exptl_absorpt_correction_type none _exptl_absorpt_correction_T_min 0.9909 _exptl_absorpt_correction_T_max 0.9922 # For a Kappa CCD, set Tmin to 1.0 and # Tmax to the ratio of max:min frame scales in scale_all.log _diffrn_measurement_device_type 'Nonius KappaCCD' _diffrn_radiation_monochromator graphite _diffrn_radiation_probe x-ray _diffrn_radiation_type 'Mo K\a' _diffrn_radiation_wavelength 0.71073 _diffrn_measurement_method '\f & \w scans' # If a reference occurs more than once, delete the author # and date from subsequent references. _computing_data_collection 'COLLECT (Nonius, 1997-2001).' _computing_cell_refinement 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_data_reduction 'DENZO/SCALEPACK (Otwinowski & Minor, 1997)' _computing_structure_solution 'SIR97 (Altomare et al., 1999)' _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 3192 _reflns_number_total 2078 _diffrn_reflns_av_R_equivalents 0.042 # Number of reflections with Friedels Law is 2078 # Number of reflections without Friedels Law is 0 # Theoretical number of reflections is about 2160 _diffrn_reflns_theta_min 2.084 _diffrn_reflns_theta_max 27.743 _diffrn_measured_fraction_theta_max 0.969 _diffrn_reflns_theta_full 25.246 _diffrn_measured_fraction_theta_full 0.994 _diffrn_reflns_limit_h_min -7 _diffrn_reflns_limit_h_max 6 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_limit_l_max 13 _reflns_limit_h_min -7 _reflns_limit_h_max 6 _reflns_limit_k_min -11 _reflns_limit_k_max 10 _reflns_limit_l_min 0 _reflns_limit_l_max 13 _oxford_diffrn_Wilson_B_factor 0.00 _oxford_diffrn_Wilson_scale 0.00 _atom_sites_solution_primary direct #heavy,direct,difmap,geom # _atom_sites_solution_secondary difmap _atom_sites_solution_hydrogens geom _refine_diff_density_min -0.20 _refine_diff_density_max 0.20 _refine_ls_number_reflns 1005 _refine_ls_number_restraints 0 _refine_ls_number_parameters 145 #_refine_ls_R_factor_ref 0.0467 _refine_ls_wR_factor_ref 0.0567 _refine_ls_goodness_of_fit_ref 1.0578 #_reflns_number_all 2072 _refine_ls_R_factor_all 0.1193 _refine_ls_wR_factor_all 0.1150 # The I/u(I) cutoff below was used for refinement as # well as the _gt R-factors: _reflns_threshold_expression I>2.0\s(I) _reflns_number_gt 1005 _refine_ls_R_factor_gt 0.0467 _refine_ls_wR_factor_gt 0.0567 _refine_ls_shift/su_max 0.000264 # 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: 0.603 0.477 0.354 ; _publ_section_abstract # Text of the abstract # (a) The Abstract must be self-contained and comprehensible # without the rest of the paper. This means no references # to atom names or to compound numbers; compounds must be # identified as the title compound, or by name or by some other # means such as derivatives of each other (e.g. "the # corresponding ketone"). # (b) The chemical formula of "the title compound" must be given. # (c) Any crystallographic molecular symmetry should be # mentioned, and also the presence of more than one molecule # in the asymmetric unit (i.e. anything other than Z'=1). ; ? ; _publ_section_comment # Text of the paper # Note that atoms are referenced as N2, not N(2) or N~2~ # If text containing () occur within (), the outer ones should be [] # Figures should be referenced as Fih. ; ? ; _publ_section_acknowledgements # Acknowledgments ; ? ; _publ_section_figure_captions # Captions to figures - Start each caption on a new line after a blank line ; Fig. 1. The title compound with displacement ellipsoids drawn at the 50% probability level. H atoms are shown as spheres of arbitary radius. ; _publ_section_exptl_refinement # Some potentially useful phrases are donated by Bill Clegg: ; In the absence of significant anomalous scattering, Friedel pairs were merged. The absolute configuration was arbitrarily assigned. The relatively large ratio of minimum to maximum corrections applied in the multiscan process (1:nnn) reflect changes in the illuminated volume of the crystal. Changes in illuminated volume were kept to a minimum, and were taken into account (G\"orbitz, 1999) by the multi-scan inter-frame scaling (DENZO/SCALEPACK, Otwinowski & Minor, 1997). G\"orbitz, C. H. (1999). Acta Cryst. B55, 1090-1098. The H atoms were all located in a difference map, but those attached to carbon atoms were repositioned geometrically. The H atoms were initially refined with soft restraints on the bond lengths and angles to regularise their geometry (C---H in the range 0.93--0.98, N---H in the range 0.86--0.89 N---H to 0.86 O---H = 0.82 \%A) and U~iso~(H) (in the range 1.2-1.5 times U~eq~ of the parent atom), after which the positions were refined with riding constraints. ; _publ_section_exptl_prep # Brief details or a reference. Include solvent if known ; ? ; # End of 'script/refcif.dat' # Insert your own references if required - in alphabetical order _publ_section_references ; Altomare, A., Burla, M.C., Camalli, M., Cascarano, G.L., Giacovazzo, C., Guagliardi, A., Grazia, A., Moliterni, G., Polidori, G. & Spagna, R. (1999). J. App. Cryst. 32, 115-119. Betteridge, P.W., Carruthers, J.R., Cooper, R.I., Prout, K. & Watkin, D.J. (2003). J. Appl. Cryst. 36, 1487. Larson, A.C. (1970) Crystallographic Computing, Ed Ahmed, F.R., Munksgaard, Copenhagen, 291-294. Nonius (1997-2001). COLLECT. Nonius BV, Delft, The Netherlands. Otwinowski, Z. & Minor, W. (1997). Methods in Enzymology, Vol. 276, edited by C. W. Carter Jr & R. M. Sweet, pp. 307--326. New York: Academic Press. Prince, E. Mathematical Techniques in Crystallography and Materials Science Springer-Verlag, New York, 1982. Watkin D.J. (1994). Acta Cryst, A50, 411-437. Watkin, D.J., Prout, C.K. & Pearce, L.J. (1996). CAMERON, Chemical Crystallography Laboratory, Oxford, UK. ; # Uequiv = arithmetic mean of Ui i.e. Ueqiv = (U1+U2+U3)/3 # Replace last . with number of unfound hydrogen atomsattached to an atom. # ..._refinement_flags_... # . no refinement constraints S special position constraint on site # G rigid group refinement of site R riding atom # D distance or angle restraint on site T thermal displacement constraints # U Uiso or Uij restraint (rigid bond) P partial occupancy constraint loop_ _atom_site_label _atom_site_type_symbol _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_occupancy _atom_site_adp_type _atom_site_refinement_flags_posn _atom_site_refinement_flags_adp _atom_site_refinement_flags_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_attached_hydrogens O1 O 0.1677(5) 0.6726(3) 0.8656(2) 0.0639 1.0000 Uani . . . . . . C13 C 0.0155(5) 0.4236(4) 0.6814(3) 0.0395 1.0000 Uani . . . . . . N3 N -0.3669(5) 0.3862(3) 0.8330(3) 0.0464 1.0000 Uani . . . . . . O4 O -0.2209(4) 0.6277(3) 1.0054(2) 0.0541 1.0000 Uani . . . . . . O2 O -0.5240(4) 0.1438(3) 0.6663(3) 0.0617 1.0000 Uani . . . . . . O5 O 0.4146(5) 0.3320(3) 0.3483(2) 0.0602 1.0000 Uani . . . . . . O7 O 0.1672(5) 0.0921(3) 0.2617(2) 0.0583 1.0000 Uani . . . . . . N4 N 0.1761(5) 0.4163(3) 0.5874(3) 0.0424 1.0000 Uani . . . . . . C5 C -0.1038(6) 0.1894(4) 0.4988(3) 0.0443 1.0000 Uani . . . . . . C6 C -0.3631(6) 0.2606(4) 0.7058(3) 0.0452 1.0000 Uani . . . . . . C7 C -0.1601(6) 0.2853(4) 0.6293(3) 0.0411 1.0000 Uani . . . . . . C8 C -0.2027(5) 0.5257(4) 0.8935(3) 0.0433 1.0000 Uani . . . . . . C9 C 0.2474(6) 0.2357(4) 0.3564(3) 0.0451 1.0000 Uani . . . . . . C10 C 0.0176(6) 0.5518(4) 0.8137(3) 0.0441 1.0000 Uani . . . . . . C11 C 0.1048(6) 0.2731(4) 0.4758(3) 0.0440 1.0000 Uani . . . . . . C12 C 0.2967(9) 0.0446(5) 0.1403(4) 0.0728 1.0000 Uani . . . . . . H51 H -0.1885 0.0910 0.4394 0.0502 1.0000 Uiso R . . . . . H121 H 0.2323 -0.0667 0.0839 0.1038 1.0000 Uiso R . . . . . H122 H 0.4727 0.0490 0.1668 0.1041 1.0000 Uiso R . . . . . H123 H 0.2670 0.1174 0.0926 0.1041 1.0000 Uiso R . . . . . H1 H 0.3005 0.4877 0.5965 0.0504 1.0000 Uiso R . . . . . H2 H -0.4869 0.3749 0.8818 0.0537 1.0000 Uiso R . . . . . loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_23 _atom_site_aniso_U_13 _atom_site_aniso_U_12 O1 0.0670(16) 0.0551(14) 0.0485(14) -0.0021(11) 0.0167(11) -0.0208(13) C13 0.0370(15) 0.0384(16) 0.0400(16) 0.0129(13) 0.0037(13) -0.0051(13) N3 0.0415(14) 0.0502(15) 0.0434(15) 0.0131(13) 0.0120(11) -0.0050(12) O4 0.0560(14) 0.0515(14) 0.0437(13) 0.0047(11) 0.0161(10) -0.0038(11) O2 0.0539(15) 0.0554(15) 0.0633(15) 0.0121(12) 0.0075(11) -0.0171(12) O5 0.0625(15) 0.0518(13) 0.0541(15) 0.0073(11) 0.0168(11) -0.0130(12) O7 0.0752(17) 0.0398(13) 0.0445(14) -0.0009(11) 0.0128(12) -0.0070(12) N4 0.0414(13) 0.0425(14) 0.0387(14) 0.0108(11) 0.0081(11) -0.0041(11) C5 0.0458(18) 0.0371(15) 0.0429(18) 0.0093(14) 0.0013(14) -0.0053(13) C6 0.0436(19) 0.0452(17) 0.0437(18) 0.0134(14) 0.0062(14) 0.0024(15) C7 0.0439(17) 0.0367(15) 0.0384(16) 0.0104(13) 0.0034(13) -0.0007(13) C8 0.0407(17) 0.0419(17) 0.0433(19) 0.0129(16) 0.0045(14) -0.0025(15) C9 0.0500(18) 0.0411(17) 0.0406(18) 0.0116(15) 0.0050(14) 0.0035(15) C10 0.0455(18) 0.0415(17) 0.0389(16) 0.0094(14) 0.0047(13) -0.0042(15) C11 0.0510(18) 0.0378(16) 0.0394(17) 0.0101(14) 0.0066(14) 0.0023(15) C12 0.104(3) 0.059(2) 0.046(2) 0.0045(18) 0.029(2) 0.008(2) _refine_ls_extinction_method None _oxford_refine_ls_scale 0.628(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 O1 . C10 . 1.203(4) yes C13 . N4 . 1.354(4) yes C13 . C7 . 1.385(4) yes C13 . C10 . 1.439(4) yes N3 . C6 . 1.397(4) yes N3 . C8 . 1.362(4) yes N3 . H2 . 0.879 no O4 . C8 . 1.213(3) yes O2 . C6 . 1.210(3) yes O5 . C9 . 1.216(4) yes O7 . C9 . 1.305(4) yes O7 . C12 . 1.450(4) yes N4 . C11 . 1.374(4) yes N4 . H1 . 0.854 no C5 . C7 . 1.401(4) yes C5 . C11 . 1.379(4) yes C5 . H51 . 0.920 no C6 . C7 . 1.457(4) yes C8 . C10 . 1.556(4) yes C9 . C11 . 1.476(5) yes C12 . H121 . 0.960 no C12 . H122 . 0.954 no C12 . H123 . 0.963 no loop_ _geom_angle_atom_site_label_1 _geom_angle_site_symmetry_1 _geom_angle_atom_site_label_2 _geom_angle_site_symmetry_2 _geom_angle_atom_site_label_3 _geom_angle_site_symmetry_3 _geom_angle _geom_angle_publ_flag N4 . C13 . C7 . 108.7(3) yes N4 . C13 . C10 . 127.4(3) yes C7 . C13 . C10 . 123.9(3) yes C6 . N3 . C8 . 127.8(3) yes C6 . N3 . H2 . 117.3 no C8 . N3 . H2 . 114.9 no C9 . O7 . C12 . 116.1(3) yes C13 . N4 . C11 . 107.9(3) yes C13 . N4 . H1 . 125.9 no C11 . N4 . H1 . 126.2 no C7 . C5 . C11 . 106.2(3) yes C7 . C5 . H51 . 127.5 no C11 . C5 . H51 . 126.3 no N3 . C6 . O2 . 119.7(3) yes N3 . C6 . C7 . 115.1(3) yes O2 . C6 . C7 . 125.1(3) yes C6 . C7 . C5 . 130.7(3) yes C6 . C7 . C13 . 121.5(3) yes C5 . C7 . C13 . 107.8(3) yes N3 . C8 . O4 . 123.0(3) yes N3 . C8 . C10 . 117.5(3) yes O4 . C8 . C10 . 119.6(3) yes O7 . C9 . O5 . 125.1(3) yes O7 . C9 . C11 . 112.2(3) yes O5 . C9 . C11 . 122.6(3) yes C8 . C10 . C13 . 114.1(3) yes C8 . C10 . O1 . 118.9(3) yes C13 . C10 . O1 . 127.0(3) yes C9 . C11 . C5 . 131.4(3) yes C9 . C11 . N4 . 119.1(3) yes C5 . C11 . N4 . 109.4(3) yes O7 . C12 . H121 . 107.6 no O7 . C12 . H122 . 108.9 no H121 . C12 . H122 . 108.9 no O7 . C12 . H123 . 109.6 no H121 . C12 . H123 . 110.9 no H122 . C12 . H123 . 110.8 no loop_ _geom_hbond_atom_site_label_D _geom_hbond_site_symmetry_D _geom_hbond_atom_site_label_H _geom_hbond_site_symmetry_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_angle_DHA _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_publ_flag N4 . H1 . O5 2_666 170 0.85 2.00 2.843(2) yes N3 . H2 . O4 2_467 174 0.88 2.05 2.924(2) yes