#------------------------------------------------------------------------------ #$Date: 2015-01-23 14:30:19 +0200 (Fri, 23 Jan 2015) $ #$Revision: 130086 $ #$URL: file:///home/coder/svn-repositories/cod/cif/2/01/17/2011709.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_2011709 loop_ _publ_author_name 'Varma, Ashok K.' 'Nangia, Ashwini' 'Desiraju, Gautam R.' 'Giri, Venkatachalam S.' 'Jaisankar, Parasuraman' _publ_section_title ; Hydrogen bonding in two tetracyclic indole alkaloids ; _journal_issue 1 _journal_name_full 'Acta Crystallographica Section C' _journal_page_first 97 _journal_page_last 99 _journal_paper_doi 10.1107/S0108270100014220 _journal_volume 57 _journal_year 2001 _chemical_formula_moiety 'C17 H14 N2 O2 , H2 O' _chemical_formula_sum 'C17 H16 N2 O3' _chemical_formula_weight 296.32 _chemical_melting_point 543 _chemical_name_common ; 3-Acetyl-4-oxo-6,7-dihydro-12H-indolo[2,3-a]quinolizine monohytrate ; _chemical_name_systematic ; 3-Acetyl-4-oxo-6,7-dihydro-12H-indolo[2,3-a]quinolizine monohydrate ; _space_group_IT_number 2 _symmetry_cell_setting triclinic _symmetry_space_group_name_Hall '-P 1' _symmetry_space_group_name_H-M 'P -1' _cell_angle_alpha 94.82(3) _cell_angle_beta 108.84(3) _cell_angle_gamma 90.96(3) _cell_formula_units_Z 2 _cell_length_a 7.307(15) _cell_length_b 9.405(2) _cell_length_c 10.989(2) _cell_measurement_reflns_used 25 _cell_measurement_temperature 293(2) _cell_measurement_theta_max 18.24 _cell_measurement_theta_min 9.12 _cell_volume 711.4(15) _computing_cell_refinement 'CAD4 Software' _computing_data_collection 'CAD4 Software (Enraf-Nonius, 1989)' _computing_data_reduction 'XTAL (Hall et al., 1995)' _computing_molecular_graphics 'PLUTON-(C) (Spek, 1979-1997)' _computing_publication_material SHELXL97 _computing_structure_refinement 'SHELXL97 (Sheldrick, 1997)' _computing_structure_solution 'SHELXS86 (Sheldrick, 1990)' _diffrn_ambient_temperature 293(2) _diffrn_measured_fraction_theta_full 1.000 _diffrn_measured_fraction_theta_max 1.000 _diffrn_measurement_device CAD-4 _diffrn_measurement_method '\w scan' _diffrn_radiation_monochromator graphite _diffrn_radiation_source 'fine-focus sealed tube' _diffrn_radiation_type MoK\a _diffrn_radiation_wavelength .71073 _diffrn_reflns_av_R_equivalents .0000 _diffrn_reflns_av_sigmaI/netI .0909 _diffrn_reflns_limit_h_max 8 _diffrn_reflns_limit_h_min 0 _diffrn_reflns_limit_k_max 11 _diffrn_reflns_limit_k_min -11 _diffrn_reflns_limit_l_max 12 _diffrn_reflns_limit_l_min -13 _diffrn_reflns_number 2490 _diffrn_reflns_theta_full 24.97 _diffrn_reflns_theta_max 24.97 _diffrn_reflns_theta_min 1.97 _diffrn_standards_decay_% 0 _diffrn_standards_interval_count 100 _diffrn_standards_number 3 _exptl_absorpt_coefficient_mu .096 _exptl_absorpt_correction_type none _exptl_crystal_colour orange _exptl_crystal_density_diffrn 1.383 _exptl_crystal_density_meas ? _exptl_crystal_density_method 'not measured' _exptl_crystal_description needles _exptl_crystal_F_000 312 _exptl_crystal_size_max .48 _exptl_crystal_size_mid .36 _exptl_crystal_size_min .28 _refine_diff_density_max .245 _refine_diff_density_min -.196 _refine_ls_extinction_coef .038(4) _refine_ls_extinction_method 'SHELXL97 (Sheldrick, 1997)' _refine_ls_goodness_of_fit_all 1.031 _refine_ls_goodness_of_fit_ref 1.156 _refine_ls_hydrogen_treatment mixed _refine_ls_matrix_type full _refine_ls_number_parameters 208 _refine_ls_number_reflns 2490 _refine_ls_number_restraints 0 _refine_ls_restrained_S_all 1.031 _refine_ls_restrained_S_obs 1.156 _refine_ls_R_factor_all .1574 _refine_ls_R_factor_gt .0624 _refine_ls_shift/esd_mean .000 _refine_ls_shift/su_max <0.001 _refine_ls_structure_factor_coef Fsqd _refine_ls_weighting_details 'calc w = 1/[\s^2^(Fo^2^)+(0.0604P)^2^] where P=(Fo^2^+2Fc^2^)/3' _refine_ls_weighting_scheme calc _refine_ls_wR_factor_all .1668 _refine_ls_wR_factor_ref .1167 _reflns_number_gt 1072 _reflns_number_total 2490 _reflns_threshold_expression I>2\s(I) _[local]_cod_data_source_file fr1299.cif _[local]_cod_data_source_block 2 _[local]_cod_cif_authors_sg_H-M 'P - 1' _cod_depositor_comments ; The following automatic conversions were performed: '_chemical_melting_point' value '543K' was changed to '543' - the value should be numeric and without a unit designator. Automatic conversion script Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana The following automatic conversions were performed: '_chemical_melting_point' value '543K' was changed to '543' - the value should be numeric and without a unit designator. Automatic conversion script Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana The following automatic conversions were performed: '_exptl_crystal_density_meas' value 'none' was changed to '?' - the value is perceived as not measured. Automatic conversion script Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas ; _cod_original_cell_volume 712(2) _cod_database_code 2011709 _cod_database_fobs_code 2011709 loop_ _symmetry_equiv_pos_as_xyz 'x, y, z' '-x, -y, -z' loop_ _atom_site_label _atom_site_fract_x _atom_site_fract_y _atom_site_fract_z _atom_site_U_iso_or_equiv _atom_site_adp_type _atom_site_calc_flag _atom_site_refinement_flags _atom_site_occupancy _atom_site_disorder_assembly _atom_site_disorder_group _atom_site_type_symbol C1 .1660(5) 1.0457(4) -.3310(3) .0575(11) Uani d . 1 . . C H1A .1212 .9649 -.3889 .069 Uiso calc R 1 . . H C2 .1997(5) 1.1742(4) -.3748(4) .0631(12) Uani d . 1 . . C H2A .1791 1.1795 -.4623 .076 Uiso calc R 1 . . H C3 .2648(5) 1.2962(4) -.2875(4) .0610(12) Uani d . 1 . . C H3A .2856 1.3819 -.3186 .073 Uiso calc R 1 . . H C4 .2986(5) 1.2928(4) -.1576(4) .0537(11) Uani d . 1 . . C H4A .3400 1.3747 -.1008 .064 Uiso calc R 1 . . H C5 .2688(5) 1.1621(4) -.1132(3) .0442(9) Uani d . 1 . . C C6 .2001(5) 1.0384(4) -.1984(3) .0444(9) Uani d . 1 . . C C7 .1850(5) .9281(3) -.1214(3) .0422(9) Uani d . 1 . . C C8 .2472(4) .9857(3) .0036(3) .0378(8) Uani d . 1 . . C C9 .2567(5) .9114(3) .1142(3) .0399(9) Uani d . 1 . . C C10 .1912(6) .6915(4) -.0396(3) .0571(11) Uani d . 1 . . C H10A .1084 .6063 -.0515 .069 Uiso calc R 1 . . H H10B .3170 .6609 -.0404 .069 Uiso calc R 1 . . H C11 .1078(5) .7777(4) -.1523(3) .0536(11) Uani d . 1 . . C H11A .1391 .7355 -.2263 .064 Uiso calc R 1 . . H H11B -.0321 .7755 -.1748 .064 Uiso calc R 1 . . H C12 .3024(5) .9745(4) .2362(3) .0473(10) Uani d . 1 . . C H12A .3302 1.0725 .2528 .057 Uiso calc R 1 . . H C13 .3075(5) .8927(4) .3361(3) .0517(10) Uani d . 1 . . C H13A .3372 .9371 .4195 .062 Uiso calc R 1 . . H C14 .2699(5) .7476(4) .3154(3) .0491(10) Uani d . 1 . . C C15 .2282(5) .6782(4) .1880(3) .0486(10) Uani d . 1 . . C C16 .2832(6) .6692(4) .4284(4) .0636(12) Uani d . 1 . . C C17 .1977(6) .5208(4) .4120(4) .0793(14) Uani d . 1 . . C H17A .2199 .4868 .4953 .119 Uiso calc R 1 . . H H17B .2572 .4595 .3628 .119 Uiso calc R 1 . . H H17C .0610 .5205 .3674 .119 Uiso calc R 1 . . H N1 .2954(4) 1.1288(3) .0089(3) .0467(8) Uani d . 1 . . N H1B .3354 1.1870 .0777 .056 Uiso calc R 1 . . H N2 .2145(4) .7664(3) .0896(2) .0423(8) Uani d . 1 . . N O1 .2090(4) .5469(3) .1593(2) .0641(8) Uani d . 1 . . O O2 .3593(5) .7280(3) .5366(3) .1071(13) Uani d . 1 . . O O3 .5232(5) .6586(3) .7891(3) .0751(10) Uani d . 1 . . O H3B .463(7) .674(5) .703(4) .119(18) Uiso d . 1 . . H H3C .611(8) .602(6) .797(5) .16(3) Uiso d . 1 . . H 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 C1 .056(2) .069(3) .047(2) .001(2) .0151(19) .013(2) C2 .055(2) .087(3) .047(2) -.001(2) .0107(19) .026(2) C3 .053(2) .070(3) .061(3) -.003(2) .015(2) .026(2) C4 .044(2) .050(2) .063(3) .0028(18) .0096(19) .0163(19) C5 .043(2) .046(2) .043(2) .0032(17) .0119(16) .0109(17) C6 .0335(19) .053(2) .047(2) -.0028(17) .0138(16) .0075(18) C7 .040(2) .041(2) .047(2) -.0005(16) .0139(16) .0102(17) C8 .0387(19) .0347(19) .0401(19) .0000(16) .0120(15) .0084(16) C9 .0402(19) .039(2) .040(2) .0071(16) .0100(16) .0098(16) C10 .071(3) .048(2) .048(2) -.002(2) .015(2) -.0018(19) C11 .057(2) .055(2) .043(2) -.0047(19) .0068(18) .0061(18) C12 .055(2) .042(2) .044(2) .0034(18) .0133(18) .0059(17) C13 .055(2) .060(3) .039(2) .008(2) .0150(18) .0042(19) C14 .048(2) .056(2) .044(2) .0065(19) .0134(17) .0118(18) C15 .041(2) .051(2) .051(2) .0008(18) .0089(17) .0107(19) C16 .077(3) .060(3) .059(3) .024(2) .027(2) .014(2) C17 .093(3) .082(3) .076(3) .015(3) .037(3) .039(2) N1 .0560(18) .0425(18) .0407(17) -.0002(14) .0146(14) .0033(14) N2 .0461(17) .0410(17) .0389(16) .0047(14) .0117(13) .0073(14) O1 .087(2) .0434(16) .0570(17) .0002(14) .0131(14) .0165(13) O2 .175(4) .090(2) .0470(18) .016(2) .019(2) .0210(17) O3 .103(2) .0631(19) .0500(18) .0149(18) .0123(17) .0005(15) loop_ _atom_type_symbol _atom_type_description _atom_type_scat_dispersion_real _atom_type_scat_dispersion_imag _atom_type_scat_source C C .0033 .0016 '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' N N .0061 .0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4' O O .0106 .0060 '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 C2 C1 C6 119.4(4) C2 C1 H1A 120.3 C6 C1 H1A 120.3 C1 C2 C3 120.1(4) C1 C2 H2A 119.9 C3 C2 H2A 119.9 C4 C3 C2 121.8(4) C4 C3 H3A 119.1 C2 C3 H3A 119.1 C3 C4 C5 117.9(4) C3 C4 H4A 121.0 C5 C4 H4A 121.0 N1 C5 C4 129.8(3) N1 C5 C6 108.5(3) C4 C5 C6 121.7(3) C1 C6 C5 119.0(3) C1 C6 C7 134.6(3) C5 C6 C7 106.4(3) C8 C7 C6 107.1(3) C8 C7 C11 119.5(3) C6 C7 C11 133.3(3) C7 C8 N1 109.7(3) C7 C8 C9 125.9(3) N1 C8 C9 124.4(3) C12 C9 N2 120.1(3) C12 C9 C8 124.4(3) N2 C9 C8 115.5(3) N2 C10 C11 115.4(3) N2 C10 H10A 108.4 C11 C10 H10A 108.4 N2 C10 H10B 108.4 C11 C10 H10B 108.4 H10A C10 H10B 107.5 C7 C11 C10 111.2(3) C7 C11 H11A 109.4 C10 C11 H11A 109.4 C7 C11 H11B 109.4 C10 C11 H11B 109.4 H11A C11 H11B 108.0 C9 C12 C13 119.7(3) C9 C12 H12A 120.1 C13 C12 H12A 120.1 C14 C13 C12 121.7(3) C14 C13 H13A 119.2 C12 C13 H13A 119.2 C13 C14 C15 119.4(3) C13 C14 C16 117.7(3) C15 C14 C16 122.8(3) O1 C15 N2 118.2(3) O1 C15 C14 125.2(4) N2 C15 C14 116.5(3) O2 C16 C14 119.5(4) O2 C16 C17 119.5(4) C14 C16 C17 120.9(3) C16 C17 H17A 109.5 C16 C17 H17B 109.5 H17A C17 H17B 109.5 C16 C17 H17C 109.5 H17A C17 H17C 109.5 H17B C17 H17C 109.5 C5 N1 C8 108.2(3) C5 N1 H1B 125.9 C8 N1 H1B 125.9 C9 N2 C15 122.3(3) C9 N2 C10 121.0(3) C15 N2 C10 115.6(3) H3B O3 H3C 111(5) loop_ _geom_bond_atom_site_label_1 _geom_bond_atom_site_label_2 _geom_bond_site_symmetry_2 _geom_bond_distance _geom_bond_publ_flag C1 C2 . 1.385(5) ? C1 C6 . 1.404(5) ? C1 H1A . .9300 ? C2 C3 . 1.402(5) ? C2 H2A . .9300 ? C3 C4 . 1.371(5) ? C3 H3A . .9300 ? C4 C5 . 1.399(5) ? C4 H4A . .9300 ? C5 N1 . 1.357(4) ? C5 C6 . 1.406(4) ? C6 C7 . 1.417(4) ? C7 C8 . 1.360(4) ? C7 C11 . 1.485(4) ? C8 N1 . 1.377(4) ? C8 C9 . 1.436(4) ? C9 C12 . 1.354(4) ? C9 N2 . 1.377(4) ? C10 N2 . 1.488(4) ? C10 C11 . 1.503(4) ? C10 H10A . .9700 ? C10 H10B . .9700 ? C11 H11A . .9700 ? C11 H11B . .9700 ? C12 C13 . 1.384(4) ? C12 H12A . .9300 ? C13 C14 . 1.373(5) ? C13 H13A . .9300 ? C14 C15 . 1.429(5) ? C14 C16 . 1.474(5) ? C15 O1 . 1.242(4) ? C15 N2 . 1.397(4) ? C16 O2 . 1.217(4) ? C16 C17 . 1.493(5) ? C17 H17A . .9600 ? C17 H17B . .9600 ? C17 H17C . .9600 ? N1 H1B . .8600 ? O3 H3B . .93(5) ? O3 H3C . .82(6) ? 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 N1 H1B O3 2_676 .86 1.98 2.819(4) 164(4) O3 H3C O1 2_666 .83(6) 1.92(6) 2.735(4) 168(6) O3 H3B O2 1_555 .93(5) 1.86(5) 2.783(4) 173(4) C10 H10B O3 1_554 .97 2.76 3.522(6) 136(3)