#------------------------------------------------------------------------------
#$Date: 2016-02-20 00:18:51 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176760 $
#$URL: svn://www.crystallography.net/cod/cif/2/01/06/2010622.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_2010622
loop_
_publ_author_name
'Camus, Fabrice'
'Norberg, Bernadette'
'Legrand, Anne'
'Rigo, Benoit'
'Durant, François'
'Wouters, Johan'
_publ_section_title
;
 Structural analysis of pyrrolidinones
;
_journal_issue                   2
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              193
_journal_page_last               196
_journal_paper_doi               10.1107/S0108270199013037
_journal_volume                  56
_journal_year                    2000
_chemical_formula_sum            'C24 H23 N O4'
_chemical_formula_weight         389.43
_chemical_name_systematic
;
5-(3,4,5-trimethoxyphenyl)-1,2,3,5-tetrahydro-11a-naphto[1,8-f,g]
indolizine-3-one
;
_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'
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 98.104(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.9090(10)
_cell_length_b                   8.5190(10)
_cell_length_c                   23.7930(10)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      42
_cell_measurement_theta_min      30
_cell_volume                     1988.4(3)
_computing_cell_refinement       'CAD-4 EXPRESS'
_computing_data_collection       'CAD-4 EXPRESS (Enraf-Nonius, 1992)'
_computing_data_reduction        'HELENA (Spek, 1997)'
_computing_molecular_graphics    'PLATON (Spek, 1990)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SIR92 (Altomare et al., 1993)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full .932
_diffrn_measured_fraction_theta_max .932
_diffrn_measurement_device_type  'Enraf-Nonius CAD-4'
_diffrn_measurement_method       θ/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  .012
_diffrn_reflns_av_sigmaI/netI    .0066
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            5132
_diffrn_reflns_theta_full        71.90
_diffrn_reflns_theta_max         71.90
_diffrn_reflns_theta_min         3.75
_diffrn_standards_decay_%        7
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time  '60 min'
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    .716
_exptl_absorpt_correction_T_max  .8138
_exptl_absorpt_correction_T_min  .7626
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al., 1968)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.301
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             824
_exptl_crystal_size_max          .40
_exptl_crystal_size_mid          .40
_exptl_crystal_size_min          .30
_refine_diff_density_max         .276
_refine_diff_density_min         -.232
_refine_ls_extinction_coef       .0041(4)
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 1997)'
_refine_ls_goodness_of_fit_ref   1.076
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         3899
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.076
_refine_ls_R_factor_all          .0437
_refine_ls_R_factor_gt           .0423
_refine_ls_shift/su_max          .001
_refine_ls_shift/su_mean         .000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0607P)²+0.4150P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         .1207
_reflns_number_gt                3676
_reflns_number_total             3899
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            gs1054.cif
_cod_data_source_block           III
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc w =
1/[\s^2^(Fo^2^)+(0.0607P)^2^+0.4150P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to 'w =
1/[\s^2^(Fo^2^)+(0.0607P)^2^+0.4150P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2010622
_cod_database_fobs_code          2010622
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
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 .30088(14) .64693(16) .35524(5) .0467(3) Uani d . 1 . . C
H1 .2640 .7348 .3749 .056 Uiso calc R 1 . . H
C2 .26920(14) .49576(16) .38601(5) .0476(3) Uani d . 1 . . C
C3 .36764(15) .38318(17) .40165(6) .0531(3) Uani d . 1 . . C
H3 .4559 .3975 .3935 .064 Uiso calc R 1 . . H
C4 .33435(15) .24784(17) .42978(6) .0523(3) Uani d . 1 . . C
C5 .20279(15) .22501(17) .44166(5) .0506(3) Uani d . 1 . . C
C6 .10484(14) .34057(18) .42691(6) .0537(3) Uani d . 1 . . C
C7 .13753(15) .47525(18) .39875(6) .0541(3) Uani d . 1 . . C
H7 .0715 .5515 .3884 .065 Uiso calc R 1 . . H
C8 .45099(14) .67717(15) .35587(5) .0465(3) Uani d . 1 . . C
C9 .52774(17) .74120(18) .40274(6) .0573(4) Uani d . 1 . . C
H9 .4860 .7677 .4341 .069 Uiso calc R 1 . . H
C10 .66865(17) .7676(2) .40429(7) .0644(4) Uani d . 1 . . C
H10 .7186 .8125 .4363 .077 Uiso calc R 1 . . H
C11 .73144(16) .72778(19) .35936(7) .0617(4) Uani d . 1 . . C
H11 .8246 .7451 .3609 .074 Uiso calc R 1 . . H
C12 .65752(14) .66034(16) .31017(6) .0527(3) Uani d . 1 . . C
C13 .72141(16) .61678(19) .26288(8) .0630(4) Uani d . 1 . . C
H13 .8149 .6306 .2642 .076 Uiso calc R 1 . . H
C14 .64762(17) .5550(2) .21562(7) .0655(4) Uani d . 1 . . C
H14 .6911 .5252 .1851 .079 Uiso calc R 1 . . H
C15 .50635(16) .53580(18) .21255(6) .0571(4) Uani d . 1 . . C
H15 .4571 .4947 .1797 .069 Uiso calc R 1 . . H
C16 .43913(14) .57643(15) .25709(5) .0464(3) Uani d . 1 . . C
C17 .51472(13) .63665(14) .30778(5) .0449(3) Uani d . 1 . . C
N18 .23288(11) .64794(13) .29666(4) .0461(3) Uani d . 1 . . N
C19 .11433(14) .72111(17) .27927(6) .0521(3) Uani d . 1 . . C
C20 .07753(16) .6911(2) .21641(7) .0680(4) Uani d . 1 . . C
H20A .0052 .6140 .2093 .082 Uiso calc R 1 . . H
H20B .0483 .7872 .1964 .082 Uiso calc R 1 . . H
C21 .20737(17) .6302(2) .19813(6) .0692(5) Uani d . 1 . . C
H21A .2584 .7147 .1837 .083 Uiso calc R 1 . . H
H21B .1879 .5509 .1688 .083 Uiso calc R 1 . . H
C22 .28716(14) .55932(17) .25235(6) .0495(3) Uani d . 1 . . C
H22 .2635 .4482 .2551 .059 Uiso calc R 1 . . H
O23 .42556(11) .13133(13) .44784(5) .0693(3) Uani d . 1 . . O
C24 .56536(17) .1637(2) .44757(8) .0694(5) Uani d . 1 . . C
H24A .5836 .1708 .4091 .104 Uiso calc R 1 . . H
H24B .6191 .0808 .4667 .104 Uiso calc R 1 . . H
H24C .5883 .2613 .4667 .104 Uiso calc R 1 . . H
O25 .17270(11) .09469(12) .47165(4) .0601(3) Uani d . 1 . . O
C26 .0977(2) -.0248(2) .43924(9) .0844(6) Uani d . 1 . . C
H26A .0053 .0091 .4286 .127 Uiso calc R 1 . . H
H26B .0989 -.1189 .4615 .127 Uiso calc R 1 . . H
H26C .1384 -.0454 .4057 .127 Uiso calc R 1 . . H
O27 -.01912(11) .31089(15) .44314(6) .0756(4) Uani d . 1 . . O
C28 -.11990(18) .4293(3) .43256(10) .0842(6) Uani d . 1 . . C
H28A -.1982 .4003 .4498 .126 Uiso calc R 1 . . H
H28B -.1459 .4408 .3924 .126 Uiso calc R 1 . . H
H28C -.0839 .5269 .4483 .126 Uiso calc R 1 . . H
O29 .04836(11) .79678(15) .30979(5) .0690(3) 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 .0181 .0091 '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 .0311 .0180 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O .0492 .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
N18 C1 C8 109.29(10) ?
N18 C1 C2 111.24(11) ?
C8 C1 C2 113.98(11) ?
N18 C1 H1 107.3 ?
C8 C1 H1 107.3 ?
C2 C1 H1 107.3 ?
C3 C2 C7 120.17(12) ?
C3 C2 C1 121.78(12) ?
C7 C2 C1 118.04(12) ?
C2 C3 C4 119.81(13) ?
C2 C3 H3 120.1 ?
C4 C3 H3 120.1 ?
O23 C4 C5 115.61(12) ?
O23 C4 C3 123.97(13) ?
C5 C4 C3 120.42(13) ?
O25 C5 C4 119.87(13) ?
O25 C5 C6 120.49(13) ?
C4 C5 C6 119.45(13) ?
O27 C6 C7 124.79(14) ?
O27 C6 C5 114.94(13) ?
C7 C6 C5 120.25(13) ?
C6 C7 C2 119.87(13) ?
C6 C7 H7 120.1 ?
C2 C7 H7 120.1 ?
C9 C8 C17 119.45(13) ?
C9 C8 C1 120.61(12) ?
C17 C8 C1 119.93(12) ?
C8 C9 C10 121.22(14) ?
C8 C9 H9 119.4 ?
C10 C9 H9 119.4 ?
C11 C10 C9 120.22(14) ?
C11 C10 H10 119.9 ?
C9 C10 H10 119.9 ?
C10 C11 C12 120.93(14) ?
C10 C11 H11 119.5 ?
C12 C11 H11 119.5 ?
C11 C12 C13 121.83(14) ?
C11 C12 C17 119.18(13) ?
C13 C12 C17 118.99(14) ?
C14 C13 C12 120.71(14) ?
C14 C13 H13 119.6 ?
C12 C13 H13 119.6 ?
C13 C14 C15 120.38(14) ?
C13 C14 H14 119.8 ?
C15 C14 H14 119.8 ?
C16 C15 C14 121.34(14) ?
C16 C15 H15 119.3 ?
C14 C15 H15 119.3 ?
C15 C16 C17 119.37(13) ?
C15 C16 C22 120.53(13) ?
C17 C16 C22 120.10(11) ?
C12 C17 C16 119.14(12) ?
C12 C17 C8 118.97(12) ?
C16 C17 C8 121.87(12) ?
C19 N18 C22 114.40(10) yes
C19 N18 C1 124.30(10) yes
C22 N18 C1 121.30(10) yes
O29 C19 N18 125.31(13) ?
O29 C19 C20 126.92(13) ?
N18 C19 C20 107.77(12) ?
C21 C20 C19 104.32(12) ?
C21 C20 H20A 110.9 ?
C19 C20 H20A 110.9 ?
C21 C20 H20B 110.9 ?
C19 C20 H20B 110.9 ?
H20A C20 H20B 108.9 ?
C20 C21 C22 104.58(12) ?
C20 C21 H21A 110.8 ?
C22 C21 H21A 110.8 ?
C20 C21 H21B 110.8 ?
C22 C21 H21B 110.8 ?
H21A C21 H21B 108.9 ?
N18 C22 C16 111.30(11) ?
N18 C22 C21 101.80(11) ?
C16 C22 C21 114.61(12) ?
N18 C22 H22 109.6 ?
C16 C22 H22 109.6 ?
C21 C22 H22 109.6 ?
C4 O23 C24 117.46(12) ?
O23 C24 H24A 109.5 ?
O23 C24 H24B 109.5 ?
H24A C24 H24B 109.5 ?
O23 C24 H24C 109.5 ?
H24A C24 H24C 109.5 ?
H24B C24 H24C 109.5 ?
C5 O25 C26 115.57(12) ?
O25 C26 H26A 109.5 ?
O25 C26 H26B 109.5 ?
H26A C26 H26B 109.5 ?
O25 C26 H26C 109.5 ?
H26A C26 H26C 109.5 ?
H26B C26 H26C 109.5 ?
C6 O27 C28 117.31(13) ?
O27 C28 H28A 109.5 ?
O27 C28 H28B 109.5 ?
H28A C28 H28B 109.5 ?
O27 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 N18 . 1.460(2) yes
C1 C8 . 1.508(2) yes
C1 C2 . 1.536(2) yes
C1 H1 . .9800 ?
C2 C3 . 1.3812(19) ?
C2 C7 . 1.391(2) ?
C3 C4 . 1.3958(19) ?
C3 H3 . .9300 ?
C4 O23 . 1.3700(17) ?
C4 C5 . 1.386(2) ?
C5 O25 . 1.3749(16) ?
C5 C6 . 1.392(2) ?
C6 O27 . 1.3622(17) ?
C6 C7 . 1.390(2) ?
C7 H7 . .9300 ?
C8 C9 . 1.371(2) ?
C8 C17 . 1.4251(18) ?
C9 C10 . 1.410(2) ?
C9 H9 . .9300 ?
C10 C11 . 1.354(2) ?
C10 H10 . .9300 ?
C11 C12 . 1.412(2) ?
C11 H11 . .9300 ?
C12 C13 . 1.416(2) ?
C12 C17 . 1.4225(19) ?
C13 C14 . 1.358(2) ?
C13 H13 . .9300 ?
C14 C15 . 1.401(2) ?
C14 H14 . .9300 ?
C15 C16 . 1.3732(19) ?
C15 H15 . .9300 ?
C16 C17 . 1.4226(19) ?
C16 C22 . 1.5013(19) ?
N18 C19 . 1.343(2) yes
N18 C22 . 1.460(2) yes
C19 O29 . 1.2263(17) ?
C19 C20 . 1.511(2) yes
C20 C21 . 1.507(2) yes
C20 H20A . .9700 ?
C20 H20B . .9700 ?
C21 C22 . 1.538(2) yes
C21 H21A . .9700 ?
C21 H21B . .9700 ?
C22 H22 . .9800 ?
O23 C24 . 1.4133(19) ?
C24 H24A . .9600 ?
C24 H24B . .9600 ?
C24 H24C . .9600 ?
O25 C26 . 1.422(2) ?
C26 H26A . .9600 ?
C26 H26B . .9600 ?
C26 H26C . .9600 ?
O27 C28 . 1.417(2) ?
C28 H28A . .9600 ?
C28 H28B . .9600 ?
C28 H28C . .9600 ?
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
N18 C1 C2 C3 110.99(14) ?
C8 C1 C2 C3 -13.1(2) yes
N18 C1 C2 C7 -69.92(15) ?
C8 C1 C2 C7 165.97(12) ?
C7 C2 C3 C4 .7(2) ?
C1 C2 C3 C4 179.73(13) ?
C2 C3 C4 O23 -178.75(14) ?
C2 C3 C4 C5 .6(2) ?
O23 C4 C5 O25 2.3(2) ?
C3 C4 C5 O25 -177.06(13) ?
O23 C4 C5 C6 177.38(13) ?
C3 C4 C5 C6 -2.0(2) ?
O25 C5 C6 O27 -1.6(2) ?
C4 C5 C6 O27 -176.57(13) ?
O25 C5 C6 C7 177.22(13) ?
C4 C5 C6 C7 2.2(2) ?
O27 C6 C7 C2 177.68(14) ?
C5 C6 C7 C2 -1.0(2) ?
C3 C2 C7 C6 -.5(2) ?
C1 C2 C7 C6 -179.57(13) ?
N18 C1 C8 C9 154.66(12) ?
C2 C1 C8 C9 -80.19(16) ?
N18 C1 C8 C17 -26.4(2) yes
C2 C1 C8 C17 98.75(14) ?
C17 C8 C9 C10 -.1(2) ?
C1 C8 C9 C10 178.89(13) ?
C8 C9 C10 C11 -.9(2) ?
C9 C10 C11 C12 .4(2) ?
C10 C11 C12 C13 -179.53(15) ?
C10 C11 C12 C17 1.0(2) ?
C11 C12 C13 C14 -178.69(15) ?
C17 C12 C13 C14 .8(2) ?
C12 C13 C14 C15 1.1(3) ?
C13 C14 C15 C16 -.9(3) ?
C14 C15 C16 C17 -1.1(2) ?
C14 C15 C16 C22 178.22(14) ?
C11 C12 C17 C16 176.71(12) ?
C13 C12 C17 C16 -2.75(19) ?
C11 C12 C17 C8 -1.95(19) ?
C13 C12 C17 C8 178.59(13) ?
C15 C16 C17 C12 2.93(19) ?
C22 C16 C17 C12 -176.42(12) ?
C15 C16 C17 C8 -178.45(13) ?
C22 C16 C17 C8 2.20(19) ?
C9 C8 C17 C12 1.47(19) ?
C1 C8 C17 C12 -177.48(11) ?
C9 C8 C17 C16 -177.15(12) ?
C1 C8 C17 C16 3.90(18) ?
C8 C1 N18 C19 -135.55(13) ?
C2 C1 N18 C19 97.7(2) yes
C8 C1 N18 C22 48.05(16) ?
C2 C1 N18 C22 -78.67(15) ?
C22 N18 C19 O29 177.06(14) ?
C1 N18 C19 O29 .4(2) ?
C22 N18 C19 C20 -2.17(17) ?
C1 N18 C19 C20 -178.79(13) ?
O29 C19 C20 C21 165.91(16) ?
N18 C19 C20 C21 -14.87(19) ?
C19 C20 C21 C22 24.96(19) ?
C19 N18 C22 C16 140.30(12) ?
C1 N18 C22 C16 -42.97(16) ?
C19 N18 C22 C21 17.74(16) ?
C1 N18 C22 C21 -165.52(13) ?
C15 C16 C22 N18 -164.01(13) ?
C17 C16 C22 N18 15.33(17) ?
C15 C16 C22 C21 -49.16(18) ?
C17 C16 C22 C21 130.18(14) ?
C20 C21 C22 N18 -25.57(17) ?
C20 C21 C22 C16 -145.83(14) ?
C5 C4 O23 C24 -167.00(10) yes
C3 C4 O23 C24 12.4(2) ?
C4 C5 O25 C26 -105.53(17) ?
C6 C5 O25 C26 79.5(2) yes
C7 C6 O27 C28 -2.8(2) yes
C5 C6 O27 C28 175.9(2) ?
