#------------------------------------------------------------------------------ #$Date: 2025-08-19 11:43:10 +0100 (Tue, 19 Aug 2025) $ #$Revision: 301803 $ #$URL: svn://www.crystallography.net/cod/cif/2/20/04/2200465.cif $ #------------------------------------------------------------------------------ # # This file is available in the Crystallography Open Database (COD), # http://www.crystallography.net/. The original data for this entry # were provided by IUCr Journals, http://journals.iucr.org/. # # The file may be used within the scientific community so long as # proper attribution is given to the journal article from which the # data were obtained. # data_2200465 loop_ _publ_author_name 'Umadevi, Balakrishnan' 'Stanley, Nithianantham' 'Thomas Muthiah, Packianathan' 'Bocelli, Gabriele' 'Cantoni, Andrea' _publ_section_title ; N^6^-Benzyladenine hydrobromide and the solid-state conformation of cytokinins ; _journal_issue 9 _journal_name_full 'Acta Crystallographica Section E' _journal_page_first o881 _journal_page_last o883 _journal_paper_doi 10.1107/S1600536801013629 _journal_volume 57 _journal_year 2001 _chemical_formula_iupac 'C12 H12 Br N5' _chemical_formula_moiety 'C12 H12 Br N5' _chemical_formula_sum 'C12 H12 Br N5' _chemical_formula_weight 306.16 _chemical_name_common 'N^6^-benzyladenine hydrobromide' _space_group_IT_number 14 _symmetry_cell_setting monoclinic _symmetry_space_group_name_Hall '-P 2ybc' _symmetry_space_group_name_H-M 'P 1 21/c 1' _cell_angle_alpha 90 _cell_angle_beta 93.71(2) _cell_angle_gamma 90 _cell_formula_units_Z 4 _cell_length_a 18.581(3) _cell_length_b 5.163(2) _cell_length_c 13.344(3) _cell_measurement_reflns_used 40 _cell_measurement_temperature 293 _cell_measurement_theta_max 16.29 _cell_measurement_theta_min 6.83 _cell_volume 1277.5(6) _computing_cell_refinement 'DIFABS (Walker & Stuart, 1983)' _computing_data_collection 'DIFABS (Walker & Stuart, 1983)' _computing_data_reduction 'DIFABS (Walker & Stuart, 1983)' _computing_molecular_graphics 'ZORTEP97 (Zsolnai, 1997)' _computing_publication_material 'PLATON (Spek, 1990)' _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS97 (sheldrick, 1997)' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full .641 _diffrn_measured_fraction_theta_max .641 _diffrn_measurement_device_type 'Siemens AED' _diffrn_measurement_method \w-2\q _diffrn_radiation_type CuK\a _diffrn_radiation_wavelength 1.54178 _diffrn_reflns_av_R_equivalents .1064 _diffrn_reflns_av_sigmaI/netI .0232 _diffrn_reflns_limit_h_max 22 _diffrn_reflns_limit_h_min -22 _diffrn_reflns_limit_k_max 6 _diffrn_reflns_limit_k_min 0 _diffrn_reflns_limit_l_max 15 _diffrn_reflns_limit_l_min -16 _diffrn_reflns_number 1608 _diffrn_reflns_reduction_process ; ? ; _diffrn_reflns_theta_full 69.90 _diffrn_reflns_theta_max 69.90 _diffrn_reflns_theta_min 4.77 _diffrn_standards_decay_% negligible _diffrn_standards_interval_time 60 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu 4.306 _exptl_absorpt_correction_T_max .4877 _exptl_absorpt_correction_T_min .3273 _exptl_absorpt_correction_type refdelf _exptl_absorpt_process_details '(Parkin et al., 1995)' _exptl_crystal_colour colourless _exptl_crystal_density_diffrn 1.592 _exptl_crystal_density_method 'not measured' _exptl_crystal_description needle _exptl_crystal_F_000 616 _exptl_crystal_size_max .33 _exptl_crystal_size_mid .18 _exptl_crystal_size_min .15 _refine_diff_density_max .935 _refine_diff_density_min -1.441 _refine_ls_extinction_coef .0025(5) _refine_ls_extinction_method SHELXL97 _refine_ls_goodness_of_fit_ref 1.044 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 208 _refine_ls_number_reflns 1556 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.044 _refine_ls_R_factor_all .0674 _refine_ls_R_factor_gt .0674 _refine_ls_shift/su_max .000 _refine_ls_shift/su_mean .000 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0956P)^2^+1.1524P] where P = (Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_ref .1732 _reflns_number_gt 1556 _reflns_number_total 1556 _reflns_threshold_expression I>2\s(I) _cod_data_source_file cv6033.cif _cod_data_source_block I _cod_depositor_comments ; The following automatic conversions were performed: '_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic' according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic' dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius The following automatic conversions were performed: '_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic' according to /home/saulius/struct/CIF-dictionaries/cif_core.dic dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana ; _cod_original_sg_symbol_H-M 'P 21/c' _cod_database_code 2200465 loop_ _symmetry_equiv_pos_as_xyz x,y,z -x,1/2+y,1/2-z -x,-y,-z x,1/2-y,1/2+z loop_ _atom_site_aniso_label _atom_site_aniso_U_11 _atom_site_aniso_U_22 _atom_site_aniso_U_33 _atom_site_aniso_U_12 _atom_site_aniso_U_13 _atom_site_aniso_U_23 Br1 .0661(6) .0654(6) .0464(5) .0064(4) -.0025(3) .0038(3) N1 .067(4) .063(4) .041(3) -.004(3) -.003(3) .004(3) N3 .070(4) .051(3) .045(3) .004(3) -.012(3) .007(3) N6 .054(3) .075(4) .051(3) .003(3) -.004(3) .020(3) N7 .059(4) .056(4) .049(3) .007(3) -.009(3) .007(3) N9 .062(4) .069(4) .052(3) .012(3) -.006(3) .002(3) C2 .078(5) .062(4) .042(3) -.003(4) -.006(3) .003(3) C4 .062(4) .052(4) .044(3) .001(3) -.011(3) -.006(3) C5 .061(4) .047(4) .038(3) -.003(3) -.002(3) .000(3) C6 .061(4) .052(4) .038(3) .002(3) -.006(3) .000(3) C8 .050(4) .076(5) .050(4) .006(4) -.002(3) .002(3) C10 .058(5) .132(11) .071(6) .015(6) .006(4) .039(7) C11 .047(4) .078(5) .062(4) -.002(4) .001(3) .020(4) C12 .072(5) .088(7) .082(6) .024(5) .003(4) .002(5) C13 .091(7) .109(8) .068(5) .018(6) -.005(5) -.017(5) C14 .072(6) .161(13) .064(6) .008(7) -.008(5) .028(7) C15 .071(6) .129(10) .086(7) .038(7) -.002(5) .032(7) C16 .069(5) .085(6) .059(5) .014(5) .009(4) .006(4) loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_thermal_displace_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_type_symbol Br1 .16929(4) .53176(16) .30710(5) .0596(3) Uani . . 1.000 Br N1 .2273(3) .2989(12) .0426(4) .057(2) Uani . . 1.000 N N3 .1098(4) .4556(12) .0018(4) .0560(19) Uani . . 1.000 N N6 .2478(4) -.0404(15) .1532(5) .0603(19) Uani . . 1.000 N N7 .0819(3) -.0472(14) .1658(4) .055(2) Uani . . 1.000 N N9 .0124(4) .2408(13) .0828(4) .061(2) Uani . . 1.000 N C2 .1815(5) .4583(16) -.0052(5) .061(2) Uani . . 1.000 C C4 .0817(4) .2757(14) .0612(5) .053(2) Uani . . 1.000 C C5 .1274(4) .0999(13) .1106(5) .049(2) Uani . . 1.000 C C6 .2020(4) .1146(14) .1031(5) .051(2) Uani . . 1.000 C C8 .0158(4) .0417(17) .1466(5) .059(3) Uani . . 1.000 C C10 .3251(5) -.033(3) .1476(8) .087(4) Uani . . 1.000 C C11 .3635(4) -.0937(18) .2487(6) .062(3) Uani . . 1.000 C C12 .3496(6) .039(2) .3326(8) .081(3) Uani . . 1.000 C C13 .3846(6) -.021(2) .4229(8) .090(4) Uani . . 1.000 C C14 .4354(6) -.207(3) .4295(8) .100(5) Uani . . 1.000 C C15 .4499(6) -.347(3) .3451(9) .096(5) Uani . . 1.000 C C16 .4131(5) -.289(2) .2542(7) .071(3) Uani . . 1.000 C H2 .200(4) .601(17) -.047(6) .06(2) Uiso . . 1.000 H H3 .084(4) .567(13) -.032(5) .040(18) Uiso . . 1.000 H H6 .234(3) -.178(14) .182(5) .042(18) Uiso . . 1.000 H H7 .094(3) -.167(13) .197(5) .031(17) Uiso . . 1.000 H H8 -.024(5) -.024(15) .171(7) .07(3) Uiso . . 1.000 H H10A .333(8) -.18(3) .090(11) .17(6) Uiso . . 1.000 H H10B .335(5) .125(18) .135(7) .06(3) Uiso . . 1.000 H H12 .314(4) .178(17) .328(6) .07(2) Uiso . . 1.000 H H13 .37318 .06793 .48036 .1078 Uiso . . 1.000 H H14 .455(8) -.27(3) .474(11) .17(7) Uiso . . 1.000 H H15 .486(6) -.47(2) .345(8) .10(4) Uiso . . 1.000 H H16 .420(6) -.40(3) .203(9) .11(4) Uiso . . 1.000 H loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source N N .0311 .0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' Br Br -.6763 1.2805 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' C C .0181 .0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' loop_ _geom_angle_atom_site_label_1 _geom_angle_atom_site_label_2 _geom_angle_atom_site_label_3 _geom_angle _geom_angle_publ_flag C2 N1 C6 119.3(6) yes C2 N3 C4 118.2(7) yes C6 N6 C10 124.7(8) yes C5 N7 C8 107.4(6) yes C4 N9 C8 103.5(6) yes C4 N3 H3 123(5) no C2 N3 H3 119(5) no C10 N6 H6 112(4) no C6 N6 H6 122(4) no C5 N7 H7 124(4) no C8 N7 H7 128(4) no N1 C2 N3 124.9(7) yes N9 C4 C5 112.1(6) yes N3 C4 N9 129.0(7) yes N3 C4 C5 118.9(7) yes N7 C5 C4 103.7(6) yes C4 C5 C6 120.8(6) no N7 C5 C6 135.3(6) yes N1 C6 N6 119.5(7) yes N6 C6 C5 122.8(7) yes N1 C6 C5 117.8(6) yes N7 C8 N9 113.4(7) yes N6 C10 C11 111.1(8) yes C10 C11 C12 121.8(9) no C10 C11 C16 118.5(9) no C12 C11 C16 119.6(8) no C11 C12 C13 120.6(10) no C12 C13 C14 120.7(10) no C13 C14 C15 119.6(11) no C14 C15 C16 119.3(12) no C11 C16 C15 120.0(10) no N1 C2 H2 120(4) no N3 C2 H2 115(4) no N7 C8 H8 125(6) no N9 C8 H8 121(6) no N6 C10 H10A 101(8) no N6 C10 H10B 105(6) no C11 C10 H10A 114(8) no C11 C10 H10B 106(6) no H10A C10 H10B 119(11) no C11 C12 H12 119(5) no C13 C12 H12 120(5) no C12 C13 H13 119.60 no C14 C13 H13 119.67 no C13 C14 H14 132(11) no C15 C14 H14 108(11) no C14 C15 H15 123(7) no C16 C15 H15 118(7) no C11 C16 H16 124(8) no C15 C16 H16 116(9) no loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_1 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag N1 C2 . . 1.318(10) yes N1 C6 . . 1.352(9) yes N3 C2 . . 1.342(12) yes N3 C4 . . 1.348(9) yes N6 C6 . . 1.318(10) yes N6 C10 . . 1.444(12) yes N7 C5 . . 1.384(9) yes N7 C8 . . 1.321(10) yes N9 C4 . . 1.350(10) yes N9 C8 . . 1.334(10) yes N3 H3 . . .86(7) no N6 H6 . . .85(7) no N7 H7 . . .77(7) no C4 C5 . . 1.381(10) no C5 C6 . . 1.398(11) no C10 C11 . . 1.517(13) no C11 C16 . . 1.365(13) no C11 C12 . . 1.352(13) no C12 C13 . . 1.367(15) no C13 C14 . . 1.345(17) no C14 C15 . . 1.379(18) no C15 C16 . . 1.386(15) no C2 H2 . . 1.00(8) no C8 H8 . . .89(9) no C10 H10A . . 1.10(15) no C10 H10B . . .86(9) no C12 H12 . . .98(8) no C13 H13 . . .9299 no C14 H14 . . .75(15) no C15 H15 . . .92(11) no C16 H16 . . .91(13) no loop_ _geom_contact_atom_site_label_1 _geom_contact_atom_site_label_2 _geom_contact_distance _geom_contact_site_symmetry_2 _geom_contact_publ_flag Br1 N6 3.408(7) 1_565 no Br1 N7 3.244(6) 1_565 no Br1 C5 3.491(7) . no Br1 C6 3.554(7) . no Br1 C8 3.534(8) 2_555 no Br1 C2 3.557(8) 4_555 no Br1 C2 3.631(8) 4_565 no Br1 H7 2.50(6) 1_565 no Br1 H8 2.75(9) 2_555 no Br1 H12 3.25(8) . no Br1 H6 2.60(7) 1_565 no Br1 H2 2.75(8) 4_565 no N3 N9 2.925(10) 3_565 no N6 N7 3.098(9) . no N6 Br1 3.408(7) 1_545 no N7 N6 3.098(9) . no N7 Br1 3.244(6) 1_545 no N9 C8 3.401(9) 3_555 no N9 N3 2.925(10) 3_565 no N1 H10B 2.45(9) . no N6 H12 2.80(8) . no N7 H6 2.90(6) . no N9 H3 2.12(7) 3_565 no C2 Br1 3.557(8) 4_554 no C2 Br1 3.631(8) 4_564 no C5 Br1 3.491(7) . no C6 Br1 3.554(7) . no C8 Br1 3.534(8) 2_545 no C8 N9 3.401(9) 3_555 no C8 H3 3.08(7) 3_565 no C12 H6 3.06(6) . no C13 H10A 2.92(15) 4_545 no C14 H10A 3.01(15) 4_545 no C16 H15 2.88(11) 2_655 no H2 Br1 2.75(8) 4_564 no H3 N9 2.12(7) 3_565 no H3 C8 3.08(7) 3_565 no H6 Br1 2.60(7) 1_545 no H6 N7 2.90(6) . no H6 C12 3.06(6) . no H7 Br1 2.50(6) 1_545 no H8 Br1 2.75(9) 2_545 no H10A H16 2.42(19) . no H10A C13 2.92(15) 4_544 no H10A C14 3.01(15) 4_544 no H10B N1 2.45(9) . no H12 Br1 3.25(8) . no H12 N6 2.80(8) . no H15 C16 2.88(11) 2_645 no H16 H10A 2.42(19) . no loop_ _geom_hbond_atom_site_label_D _geom_hbond_atom_site_label_H _geom_hbond_atom_site_label_A _geom_hbond_site_symmetry_A _geom_hbond_distance_DH _geom_hbond_distance_HA _geom_hbond_distance_DA _geom_hbond_angle_DHA _geom_hbond_publ_flag N3 H3 N9 3_565 .86(7) 2.12(7) 2.925(10) 156(7) yes N6 H6 Br1 1_545 .85(7) 2.60(7) 3.408(7) 159(6) yes N7 H7 Br1 1_545 .77(7) 2.50(6) 3.244(6) 161(5) yes C2 H2 Br1 4_564 1.00(8) 2.75(8) 3.631(8) 147(6) yes C8 H8 Br1 2_545 .89(9) 2.75(9) 3.534(8) 147(7) yes C10 H10B N1 . .86(9) 2.45(9) 2.806(14) 106(7) yes loop_ _geom_torsion_atom_site_label_1 _geom_torsion_atom_site_label_2 _geom_torsion_atom_site_label_3 _geom_torsion_atom_site_label_4 _geom_torsion _geom_torsion_publ_flag C6 N1 C2 N3 .7(11) no C2 N1 C6 N6 -178.1(7) no C2 N1 C6 C5 1.0(10) no C4 N3 C2 N1 -.7(11) no C2 N3 C4 N9 177.4(7) no C2 N3 C4 C5 -1.2(10) no C10 N6 C6 N1 -1.1(12) no C10 N6 C6 C5 179.8(9) no C6 N6 C10 C11 144.2(9) no C8 N7 C5 C4 .6(8) no C8 N7 C5 C6 174.9(8) no C5 N7 C8 N9 -.5(9) no C8 N9 C4 N3 -178.4(7) no C8 N9 C4 C5 .3(8) no C4 N9 C8 N7 .2(8) no N3 C4 C5 N7 178.3(6) no N3 C4 C5 C6 2.9(10) no N9 C4 C5 C6 -175.9(6) no N9 C4 C5 N7 -.5(8) no C4 C5 C6 N6 176.3(7) no C4 C5 C6 N1 -2.8(10) no N7 C5 C6 N1 -176.4(7) no N7 C5 C6 N6 2.7(13) no N6 C10 C11 C16 125.5(10) no N6 C10 C11 C12 -54.2(15) no C10 C11 C12 C13 179.5(10) no C16 C11 C12 C13 -.2(15) no C10 C11 C16 C15 179.1(10) no C12 C11 C16 C15 -1.2(15) no C11 C12 C13 C14 2.4(17) no C12 C13 C14 C15 -3.1(19) no C13 C14 C15 C16 1.6(19) no C14 C15 C16 C11 .5(17) no loop_ _cod_related_entry_id _cod_related_entry_database _cod_related_entry_code 1 ChemSpider 21132734 2 PubChem 129880902