#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/29/2012973.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_2012973
loop_
_publ_author_name
'Morel, Ademir F.'
'Gonzaga, Wellington de A.'
'Burrow, Robert A.'
'Maichle-Mössmer, Cäcilia'
'Strähle, Johannes'
_publ_section_title
;
 6-Acetonyldihydroavicine
;
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o606
_journal_page_last               o607
_journal_paper_doi               10.1107/S0108270102015202
_journal_volume                  58
_journal_year                    2002
_chemical_formula_iupac          'C23 H19 N O5'
_chemical_formula_moiety         'C23 H19 N O5'
_chemical_formula_sum            'C23 H19 N O5'
_chemical_formula_weight         389.39
_chemical_name_common
;
6-acetonyldihydroavicine
;
_chemical_name_systematic
;
1-(5-methyl-5,6-dihydro[1,3]benzodioxolo[5,6-c][1,3]dioxolo[4,5-j]
phenanthridin-6-yl)acetone
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                94.191(6)
_cell_angle_beta                 93.879(6)
_cell_angle_gamma                105.293(6)
_cell_formula_units_Z            2
_cell_length_a                   8.2525(7)
_cell_length_b                   8.2653(6)
_cell_length_c                   13.9594(6)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    213(2)
_cell_measurement_theta_max      27.06
_cell_measurement_theta_min      8.87
_cell_volume                     912.24(11)
_computing_cell_refinement       'CAD-4 EXPRESS'
_computing_data_collection       'CAD-4 EXPRESS (Enraf-Nonius, 1992)'
_computing_data_reduction        'HELENA (Spek, 1995)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 1997)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      213(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type  'Enraf-Nonius CAD-4'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.0451
_diffrn_reflns_av_sigmaI/netI    0.0420
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -1
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            3809
_diffrn_reflns_theta_full        64.94
_diffrn_reflns_theta_max         64.95
_diffrn_reflns_theta_min         5.57
_diffrn_standards_decay_%        <2
_diffrn_standards_interval_time  60
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.828
_exptl_absorpt_correction_T_max  0.921
_exptl_absorpt_correction_T_min  0.864
_exptl_absorpt_correction_type   '\y scan'
_exptl_absorpt_process_details
'with 5 reflections using the ABSPSI routine in PLATON (Spek, 1995)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.419
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             408
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.231
_refine_diff_density_min         -0.197
_refine_ls_extinction_coef       0.0064(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     267
_refine_ls_number_reflns         3107
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0713
_refine_ls_R_factor_gt           0.0444
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0627P)²+0.1711P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1113
_refine_ls_wR_factor_ref         0.1249
_reflns_number_gt                2287
_reflns_number_total             3107
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            fr1384.cif
_cod_data_source_block           I
_cod_original_cell_volume        912.25(10)
_cod_database_code               2012973
_cod_database_fobs_code          2012973
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 0.9251(2) 0.4457(2) 0.26085(15) 0.0364(5) Uani d . 1 . . C
C2 0.9819(3) 0.6139(2) 0.30341(16) 0.0403(5) Uani d . 1 . . C
H2 1.0524 0.6958 0.2705 0.048 Uiso calc R 1 . . H
C3 0.9362(3) 0.6592(2) 0.39108(16) 0.0415(5) Uani d . 1 . . C
H3 0.9786 0.7713 0.4182 0.050 Uiso calc R 1 . . H
C4 0.8266(2) 0.5420(2) 0.44253(16) 0.0385(5) Uani d . 1 . . C
C5 0.7771(3) 0.5901(3) 0.53340(16) 0.0438(5) Uani d . 1 . . C
H5 0.8162 0.7016 0.5619 0.053 Uiso calc R 1 . . H
C6 0.6722(3) 0.4705(3) 0.57735(16) 0.0435(5) Uani d . 1 . . C
O7 0.6093(2) 0.4861(2) 0.66507(12) 0.0593(5) Uani d . 1 . . O
C8 0.4987(3) 0.3258(3) 0.67673(17) 0.0521(6) Uani d . 1 . . C
H8A 0.3833 0.3351 0.6802 0.063 Uiso calc R 1 . . H
H8B 0.5338 0.2845 0.7366 0.063 Uiso calc R 1 . . H
O9 0.5051(2) 0.2119(2) 0.59622(12) 0.0597(5) Uani d . 1 . . O
C10 0.6093(3) 0.3045(3) 0.53547(16) 0.0429(5) Uani d . 1 . . C
C11 0.6499(3) 0.2506(3) 0.44921(16) 0.0414(5) Uani d . 1 . . C
H11 0.6058 0.1384 0.4225 0.050 Uiso calc R 1 . . H
C12 0.7636(2) 0.3726(2) 0.40005(15) 0.0368(5) Uani d . 1 . . C
C13 0.8160(2) 0.3272(2) 0.30921(15) 0.0357(5) Uani d . 1 . . C
N14 0.75781(19) 0.15470(19) 0.27038(12) 0.0355(4) Uani d . 1 . . N
C15 0.7375(2) 0.1346(2) 0.16421(15) 0.0359(5) Uani d . 1 . . C
H15 0.7260 0.0145 0.1439 0.043 Uiso calc R 1 . . H
C16 0.8894(2) 0.2369(2) 0.11996(15) 0.0362(5) Uani d . 1 . . C
C17 0.9359(2) 0.1753(3) 0.03309(16) 0.0390(5) Uani d . 1 . . C
H17 0.8728 0.0725 0.0000 0.047 Uiso calc R 1 . . H
C18 1.0772(2) 0.2715(3) -0.00166(16) 0.0390(5) Uani d . 1 . . C
O19 1.14947(19) 0.23701(18) -0.08428(11) 0.0518(4) Uani d . 1 . . O
C20 1.3022(3) 0.3695(3) -0.08225(17) 0.0469(6) Uani d . 1 . . C
H20A 1.3999 0.3235 -0.0755 0.056 Uiso calc R 1 . . H
H20B 1.3052 0.4235 -0.1426 0.056 Uiso calc R 1 . . H
O21 1.30803(18) 0.48984(18) -0.00258(11) 0.0493(4) Uani d . 1 . . O
C22 1.1708(2) 0.4225(2) 0.04670(15) 0.0367(5) Uani d . 1 . . C
C23 1.1264(2) 0.4872(2) 0.13053(15) 0.0374(5) Uani d . 1 . . C
H23 1.1897 0.5918 0.1616 0.045 Uiso calc R 1 . . H
C24 0.9815(2) 0.3910(2) 0.16891(15) 0.0352(5) Uani d . 1 . . C
C25 0.8613(3) 0.0526(3) 0.31112(16) 0.0440(5) Uani d . 1 . . C
H25A 0.9765 0.0944 0.2950 0.066 Uiso calc R 1 . . H
H25B 0.8166 -0.0638 0.2846 0.066 Uiso calc R 1 . . H
H25C 0.8593 0.0596 0.3807 0.066 Uiso calc R 1 . . H
C26 0.5723(2) 0.1717(3) 0.12994(17) 0.0405(5) Uani d . 1 . . C
H26A 0.5716 0.2842 0.1571 0.048(6) Uiso calc R 1 . . H
H26B 0.5624 0.1696 0.0595 0.065(8) Uiso calc R 1 . . H
C27 0.4248(2) 0.0414(3) 0.16143(16) 0.0399(5) Uani d . 1 . . C
C28 0.3008(3) 0.1003(3) 0.2164(2) 0.0683(8) Uani d . 1 . . C
H28A 0.2119 0.0040 0.2301 0.102 Uiso calc R 1 . . H
H28B 0.2524 0.1728 0.1786 0.102 Uiso calc R 1 . . H
H28C 0.3566 0.1626 0.2765 0.102 Uiso calc R 1 . . H
O29 0.41039(18) -0.10772(18) 0.14154(12) 0.0524(4) Uani d . 1 . . O
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0311 0.0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0492 0.0322 '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
C13 C1 C2 118.5(2) n
C13 C1 C24 119.14(18) n
C2 C1 C24 122.30(18) n
C3 C2 C1 121.3(2) n
C2 C3 C4 121.69(19) n
C3 C4 C5 121.60(19) n
C3 C4 C12 118.2(2) n
C5 C4 C12 120.16(19) n
C6 C5 C4 117.7(2) n
C5 C6 O7 128.2(2) n
C5 C6 C10 122.2(2) n
O7 C6 C10 109.6(2) n
C6 O7 C8 106.32(17) n
O7 C8 O9 108.43(18) n
C10 O9 C8 106.39(18) n
C11 C10 O9 127.6(2) n
C11 C10 C6 123.2(2) n
O9 C10 C6 109.18(19) n
C10 C11 C12 116.8(2) n
C13 C12 C4 119.09(19) n
C13 C12 C11 120.97(18) n
C4 C12 C11 119.9(2) n
C1 C13 C12 121.15(18) n
C1 C13 N14 120.78(19) n
C12 C13 N14 118.04(18) n
C13 N14 C25 111.69(15) y
C13 N14 C15 112.94(15) y
C25 N14 C15 112.83(16) y
N14 C15 C16 112.70(16) y
N14 C15 C26 108.82(16) y
C16 C15 C26 113.55(16) y
C17 C16 C24 121.73(18) n
C17 C16 C15 119.88(17) n
C24 C16 C15 118.38(19) n
C18 C17 C16 117.01(18) n
C17 C18 O19 127.87(19) n
C17 C18 C22 121.8(2) n
O19 C18 C22 110.29(17) n
C18 O19 C20 105.23(15) n
O21 C20 O19 108.59(16) n
C22 O21 C20 105.94(15) n
C23 C22 O21 127.98(18) n
C23 C22 C18 122.41(18) n
O21 C22 C18 109.61(18) n
C22 C23 C24 117.38(18) n
C16 C24 C23 119.62(19) n
C16 C24 C1 118.26(18) n
C23 C24 C1 122.11(18) n
C27 C26 C15 109.83(16) y
O29 C27 C28 121.6(2) n
O29 C27 C26 120.00(19) n
C28 C27 C26 118.39(19) n
C3 C2 H2 119.4 ?
C1 C2 H2 119.4 ?
C2 C3 H3 119.2 ?
C4 C3 H3 119.2 ?
C6 C5 H5 121.2 ?
C4 C5 H5 121.2 ?
O7 C8 H8A 110.0 ?
O9 C8 H8A 110.0 ?
O7 C8 H8B 110.0 ?
O9 C8 H8B 110.0 ?
H8A C8 H8B 108.4 ?
C10 C11 H11 121.6 ?
C12 C11 H11 121.6 ?
N14 C15 H15 107.1 ?
C16 C15 H15 107.1 ?
C26 C15 H15 107.1 ?
C18 C17 H17 121.5 ?
C16 C17 H17 121.5 ?
O21 C20 H20A 110.0 ?
O19 C20 H20A 110.0 ?
O21 C20 H20B 110.0 ?
O19 C20 H20B 110.0 ?
H20A C20 H20B 108.4 ?
C22 C23 H23 121.3 ?
C24 C23 H23 121.3 ?
N14 C25 H25A 109.5 ?
N14 C25 H25B 109.5 ?
H25A C25 H25B 109.5 ?
N14 C25 H25C 109.5 ?
H25A C25 H25C 109.5 ?
H25B C25 H25C 109.5 ?
C27 C26 H26A 109.7 ?
C15 C26 H26A 109.7 ?
C27 C26 H26B 109.7 ?
C15 C26 H26B 109.7 ?
H26A C26 H26B 108.2 ?
C27 C28 H28A 109.5 ?
C27 C28 H28B 109.5 ?
H28A C28 H28B 109.5 ?
C27 C28 H28C 109.5 ?
H28A C28 H28C 109.5 ?
H28B C28 H28C 109.5 ?
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 C13 . 1.393(3) n
C1 C2 . 1.415(3) n
C1 C24 . 1.475(3) y
C2 C3 . 1.360(3) n
C3 C4 . 1.414(3) n
C4 C5 . 1.420(3) n
C4 C12 . 1.427(3) n
C5 C6 . 1.347(3) n
C6 O7 . 1.373(3) y
C6 C10 . 1.400(3) y
O7 C8 . 1.424(3) y
C8 O9 . 1.425(3) y
O9 C10 . 1.375(3) y
C10 C11 . 1.347(3) n
C11 C12 . 1.435(3) n
C12 C13 . 1.423(3) n
C13 N14 . 1.431(2) y
N14 C25 . 1.466(2) y
N14 C15 . 1.472(3) y
C15 C16 . 1.513(3) n
C15 C26 . 1.528(3) n
C16 C17 . 1.397(3) n
C16 C24 . 1.400(3) y
C17 C18 . 1.368(3) n
C18 O19 . 1.379(2) y
C18 C22 . 1.381(3) y
O19 C20 . 1.432(2) y
C20 O21 . 1.426(3) y
O21 C22 . 1.377(2) y
C22 C23 . 1.364(3) n
C23 C24 . 1.413(3) n
C26 C27 . 1.511(3) n
C27 O29 . 1.216(2) n
C27 C28 . 1.479(3) n
C2 H2 . 0.9400 ?
C3 H3 . 0.9400 ?
C5 H5 . 0.9400 ?
C8 H8A . 0.9800 ?
C8 H8B . 0.9800 ?
C11 H11 . 0.9400 ?
C15 H15 . 0.9900 ?
C17 H17 . 0.9400 ?
C20 H20A . 0.9800 ?
C20 H20B . 0.9800 ?
C23 H23 . 0.9400 ?
C25 H25A . 0.9700 ?
C25 H25B . 0.9700 ?
C25 H25C . 0.9700 ?
C26 H26A . 0.9800 ?
C26 H26B . 0.9800 ?
C28 H28A . 0.9700 ?
C28 H28B . 0.9700 ?
C28 H28C . 0.9700 ?
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
C8 H8B O29 2_656 0.98 2.42 3.372(3) 164
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
C13 C1 C2 C3 2.2(3) ?
C24 C1 C2 C3 -175.95(19) ?
C1 C2 C3 C4 -1.8(3) ?
C2 C3 C4 C5 -179.03(19) ?
C2 C3 C4 C12 -0.1(3) ?
C3 C4 C5 C6 179.90(19) ?
C12 C4 C5 C6 1.0(3) ?
C4 C5 C6 O7 179.11(19) ?
C4 C5 C6 C10 -1.4(3) ?
C5 C6 O7 C8 177.5(2) ?
C10 C6 O7 C8 -2.1(2) ?
C6 O7 C8 O9 3.3(2) ?
O7 C8 O9 C10 -3.3(2) ?
C8 O9 C10 C11 -178.4(2) ?
C8 O9 C10 C6 2.0(2) ?
C5 C6 C10 C11 0.9(3) ?
O7 C6 C10 C11 -179.5(2) ?
C5 C6 C10 O9 -179.52(19) ?
O7 C6 C10 O9 0.0(2) ?
O9 C10 C11 C12 -179.36(19) ?
C6 C10 C11 C12 0.1(3) ?
C3 C4 C12 C13 1.4(3) ?
C5 C4 C12 C13 -179.61(18) ?
C3 C4 C12 C11 -178.96(18) ?
C5 C4 C12 C11 0.0(3) ?
C10 C11 C12 C13 179.06(18) ?
C10 C11 C12 C4 -0.6(3) ?
C2 C1 C13 C12 -0.8(3) ?
C24 C1 C13 C12 177.39(17) ?
C2 C1 C13 N14 -178.60(17) ?
C24 C1 C13 N14 -0.4(3) y
C4 C12 C13 C1 -1.0(3) ?
C11 C12 C13 C1 179.41(18) ?
C4 C12 C13 N14 176.87(16) ?
C11 C12 C13 N14 -2.7(3) ?
C1 C13 N14 C25 95.4(2) ?
C12 C13 N14 C25 -82.5(2) ?
C1 C13 N14 C15 -33.1(2) y
C12 C13 N14 C15 149.04(17) ?
C13 N14 C15 C16 48.3(2) y
C25 N14 C15 C16 -79.60(19) ?
C13 N14 C15 C26 -78.62(19) ?
C25 N14 C15 C26 153.53(16) ?
N14 C15 C16 C17 146.43(18) ?
C26 C15 C16 C17 -89.3(2) ?
N14 C15 C16 C24 -32.5(2) y
C26 C15 C16 C24 91.8(2) ?
C24 C16 C17 C18 0.8(3) ?
C15 C16 C17 C18 -178.12(18) ?
C16 C17 C18 O19 178.93(19) ?
C16 C17 C18 C22 0.2(3) ?
C17 C18 O19 C20 -174.8(2) ?
C22 C18 O19 C20 4.1(2) ?
C18 O19 C20 O21 -5.9(2) ?
O19 C20 O21 C22 5.5(2) ?
C20 O21 C22 C23 176.8(2) ?
C20 O21 C22 C18 -3.0(2) ?
C17 C18 C22 C23 -1.6(3) ?
O19 C18 C22 C23 179.47(18) ?
C17 C18 C22 O21 178.22(18) ?
O19 C18 C22 O21 -0.7(2) ?
O21 C22 C23 C24 -177.97(18) ?
C18 C22 C23 C24 1.9(3) ?
C17 C16 C24 C23 -0.5(3) ?
C15 C16 C24 C23 178.41(17) ?
C17 C16 C24 C1 -179.20(18) ?
C15 C16 C24 C1 -0.2(3) y
C22 C23 C24 C16 -0.8(3) ?
C22 C23 C24 C1 177.82(18) ?
C13 C1 C24 C16 17.8(3) y
C2 C1 C24 C16 -164.11(18) ?
C13 C1 C24 C23 -160.86(18) ?
C2 C1 C24 C23 17.3(3) ?
N14 C15 C26 C27 -64.9(2) ?
C16 C15 C26 C27 168.73(17) ?
C15 C26 C27 O29 -53.6(3) ?
C15 C26 C27 C28 126.3(2) y
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 8867093
