#------------------------------------------------------------------------------
#$Date: 2016-02-20 05:06:23 +0200 (Sat, 20 Feb 2016) $
#$Revision: 176774 $
#$URL: svn://www.crystallography.net/cod/cif/2/20/02/2200299.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_2200299
loop_
_publ_author_name
'Russi, Silvia'
'Mombrú, Alvaro W.'
'Gamenara, Daniela'
'Dias, Eduardo'
'Heinzen, Horacio'
'Moyna, Patrick'
'Faccio, Ricardo'
'Suescun, Leopoldo'
'Mariezcurrena, Raúl A.'
_publ_section_title
4,5,6,9-Tetramethoxy-11-phenyl-10-oxa-11-azatricyclo[7.2.2.0^2,7^]trideca-2(7),3,5,12-tetraen-8-one
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o444
_journal_page_last               o446
_journal_paper_doi               10.1107/S1600536801006286
_journal_volume                  57
_journal_year                    2001
_chemical_formula_iupac          'C21 H21 N O6'
_chemical_formula_moiety         'C21 H21 N O6'
_chemical_formula_sum            'C21 H21 N O6'
_chemical_formula_weight         383.39
_chemical_melting_point          387.5(5)
_chemical_name_systematic
;
4,5,6,9-tetramethoxy-11-phenyl-10-oxa-11-aza-tricyclo[7.2.2.0 2,7]
trideca-2(7),3,5,12-tetraen-8-one
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 115.956(14)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   13.495(2)
_cell_length_b                   10.2178(18)
_cell_length_c                   15.154(3)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      34.03
_cell_measurement_theta_min      22.84
_cell_volume                     1878.8(6)
_computing_cell_refinement       'MSC/AFC Diffractometer Control Software'
_computing_data_collection
;
MSC/AFC Diffractometer Control Software
(Molecular Structure Corporation, 1993)
;
_computing_data_reduction        'MSC/AFC Diffractometer Control Software'
_computing_molecular_graphics    'ZORTEP (Zsolnai & Pritzkow, 1995)'
_computing_publication_material
'PLATON (Spek, 1990) and CSD (Allen & Kennard, 1993)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full .999
_diffrn_measured_fraction_theta_max .999
_diffrn_measurement_device_type  'Rigaku AFC-7S'
_diffrn_measurement_method       θ/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     .71069
_diffrn_reflns_av_R_equivalents  .0465
_diffrn_reflns_av_sigmaI/netI    .0602
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -1
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -1
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            5381
_diffrn_reflns_theta_full        27.48
_diffrn_reflns_theta_max         27.48
_diffrn_reflns_theta_min         2.49
_diffrn_standards_decay_%        8.93
_diffrn_standards_interval_count 150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    .100
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.355
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             808
_exptl_crystal_size_max          .15
_exptl_crystal_size_mid          .12
_exptl_crystal_size_min          .10
_refine_diff_density_max         .224
_refine_diff_density_min         -.208
_refine_ls_extinction_coef       .0102(15)
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.010
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     259
_refine_ls_number_reflns         4300
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.010
_refine_ls_R_factor_all          .0990
_refine_ls_R_factor_gt           .0430
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         .000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0624P)²+0.3861P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         .1448
_reflns_number_gt                2466
_reflns_number_total             4300
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            cv6018.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:

'_chemical_melting_point' value '387-388 K' was changed to '387.5(5)'
- the average value was taken and precision was estimated.

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 '387-388 K' was changed to '387.5(5)'
- the average value was taken and precision was estimated.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2200299
_cod_database_fobs_code          2200299
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
C7 .00563(15) .77843(19) .14866(14) .0385(4) Uani d . 1 . . C
C6 -.08759(15) .7929(2) .16777(15) .0432(5) Uani d . 1 . . C
C5 -.07709(16) .8316(2) .25884(16) .0478(5) Uani d . 1 . . C
C4 .02604(17) .8594(2) .33397(16) .0484(5) Uani d . 1 . . C
C3 .11862(16) .8433(2) .31717(14) .0424(5) Uani d . 1 . . C
H3 .1880 .8598 .3677 .051 Uiso calc R 1 . . H
C2 .10964(14) .80323(18) .22696(14) .0365(4) Uani d . 1 . . C
C1 .21776(14) .78348(18) .21972(13) .0351(4) Uani d . 1 . . C
H1 .2786 .7896 .2858 .042 Uiso calc R 1 . . H
C12 .22504(15) .65380(18) .17618(15) .0388(4) Uani d . 1 . . C
H12 .2681 .5858 .2148 .047 Uiso calc R 1 . . H
C13 .16764(15) .64135(19) .08099(15) .0417(5) Uani d . 1 . . C
H13 .1728 .5667 .0482 .050 Uiso calc R 1 . . H
C9 .09356(15) .75240(19) .02756(13) .0386(4) Uani d . 1 . . C
O10 .14043(10) .88179(12) .06203(9) .0380(3) Uani d . 1 . . O
N11 .22991(11) .89065(15) .15848(10) .0348(4) Uani d . 1 . . N
C1' .33517(14) .89093(18) .15450(13) .0362(4) Uani d . 1 . . C
C2' .42359(15) .9407(2) .23617(15) .0459(5) Uani d . 1 . . C
H2' .4135 .9686 .2901 .046(6) Uiso calc R 1 . . H
C3' .52644(17) .9491(2) .23794(18) .0572(6) Uani d . 1 . . C
H3' .5855 .9818 .2932 .067(7) Uiso calc R 1 . . H
C4' .54176(18) .9092(3) .15815(19) .0653(7) Uani d . 1 . . C
H4' .6110 .9155 .1592 .066(7) Uiso calc R 1 . . H
C5' .4545(2) .8600(3) .07699(19) .0658(7) Uani d . 1 . . C
H5' .4652 .8326 .0232 .080(8) Uiso calc R 1 . . H
C6' .35047(17) .8505(2) .07421(15) .0507(5) Uani d . 1 . . C
H6' .2917 .8172 .0189 .048(6) Uiso calc R 1 . . H
O81 -.09261(12) .69348(19) -.01466(12) .0658(5) Uani d . 1 . . O
C61 -.24770(18) .8769(2) .04003(18) .0619(6) Uani d . 1 . . C
H61A -.3199 .8514 -.0075 .074 Uiso calc R 1 . . H
H61B -.2066 .9103 .0068 .074 Uiso calc R 1 . . H
H61C -.2540 .9436 .0819 .074 Uiso calc R 1 . . H
C51 -.2104(2) .7344(3) .2982(2) .0899(11) Uani d . 1 . . C
H51A -.2746 .7547 .3075 .108 Uiso calc R 1 . . H
H51B -.1546 .6982 .3576 .108 Uiso calc R 1 . . H
H51C -.2293 .6719 .2460 .108 Uiso calc R 1 . . H
C41 .12584(19) .9639(3) .48911(18) .0671(7) Uani d . 1 . . C
H41A .1171 .9860 .5469 .081 Uiso calc R 1 . . H
H41B .1369 1.0423 .4597 .081 Uiso calc R 1 . . H
H41C .1885 .9075 .5067 .081 Uiso calc R 1 . . H
C91 .0061(2) .8511(2) -.13090(16) .0593(6) Uani d . 1 . . C
H91A -.0072 .8362 -.1977 .071 Uiso calc R 1 . . H
H91B .0466 .9311 -.1078 .071 Uiso calc R 1 . . H
H91C -.0630 .8576 -.1273 .071 Uiso calc R 1 . . H
C8 -.00847(15) .7393(2) .04852(15) .0427(5) Uani d . 1 . . C
O61 -.19195(10) .76589(15) .09787(11) .0539(4) Uani d . 1 . . O
O51 -.16999(12) .85037(17) .27366(13) .0636(5) Uani d . 1 . . O
O41 .02894(13) .89809(19) .42060(12) .0673(5) Uani d . 1 . . O
O91 .06864(12) .74409(14) -.07090(9) .0490(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 .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'
O O .0106 .0060 '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'
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 C7 C6 117.10(17) ?
C2 C7 C8 122.61(17) y
C6 C7 C8 120.29(17) ?
O61 C6 C5 116.83(18) ?
O61 C6 C7 121.69(19) ?
C5 C6 C7 121.46(17) ?
O51 C5 C6 119.92(18) ?
O51 C5 C4 119.6(2) ?
C6 C5 C4 120.36(18) ?
O41 C4 C5 116.60(18) ?
O41 C4 C3 124.40(19) ?
C5 C4 C3 118.98(19) ?
C2 C3 C4 121.34(18) ?
C3 C2 C7 120.71(17) ?
C3 C2 C1 116.03(16) ?
C7 C2 C1 123.23(16) y
N11 C1 C12 109.18(14) y
N11 C1 C2 108.51(14) y
C12 C1 C2 113.40(15) y
C13 C12 C1 116.62(17) y
C12 C13 C9 117.08(17) y
O91 C9 O10 107.74(15) ?
O91 C9 C13 109.11(16) ?
O10 C9 C13 114.29(14) y
O91 C9 C8 113.48(15) ?
O10 C9 C8 106.83(15) y
C13 C9 C8 105.52(16) y
N11 O10 C9 117.48(12) y
O10 N11 C1' 111.19(13) ?
O10 N11 C1 108.37(13) y
C1' N11 C1 113.88(14) ?
C6' C1' C2' 119.55(17) ?
C6' C1' N11 124.26(17) ?
C2' C1' N11 116.13(16) ?
C3' C2' C1' 120.4(2) ?
C4' C3' C2' 120.1(2) ?
C5' C4' C3' 119.8(2) ?
C4' C5' C6' 120.8(2) ?
C1' C6' C5' 119.4(2) ?
O81 C8 C7 124.18(19) ?
O81 C8 C9 118.70(18) ?
C7 C8 C9 117.04(16) y
C6 O61 C61 113.65(16) ?
C5 O51 C51 113.99(18) ?
C4 O41 C41 117.98(17) ?
C9 O91 C91 115.76(16) ?
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
C7 C2 . 1.409(3) y
C7 C6 . 1.417(3) ?
C7 C8 . 1.499(3) y
C6 O61 . 1.370(2) ?
C6 C5 . 1.382(3) ?
C5 O51 . 1.381(2) ?
C5 C4 . 1.388(3) ?
C4 O41 . 1.355(3) ?
C4 C3 . 1.390(3) ?
C3 C2 . 1.380(3) ?
C2 C1 . 1.524(2) y
C1 N11 . 1.490(2) y
C1 C12 . 1.502(3) y
C12 C13 . 1.311(3) y
C13 C9 . 1.495(3) y
C9 O91 . 1.381(2) ?
C9 O10 . 1.460(2) y
C9 C8 . 1.548(3) y
O10 N11 . 1.4345(18) y
N11 C1' . 1.448(2) ?
C1' C6' . 1.383(3) ?
C1' C2' . 1.386(3) ?
C2' C3' . 1.379(3) ?
C3' C4' . 1.375(3) ?
C4' C5' . 1.373(4) ?
C5' C6' . 1.390(3) ?
O81 C8 . 1.214(2) ?
C61 O61 . 1.430(3) ?
C51 O51 . 1.420(3) ?
C41 O41 . 1.432(3) ?
C91 O91 . 1.437(3) ?
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
C2 C7 C6 O61 -177.24(17) ?
C8 C7 C6 O61 3.2(3) ?
C2 C7 C6 C5 .9(3) ?
C8 C7 C6 C5 -178.60(19) ?
O61 C6 C5 O51 -4.6(3) ?
C7 C6 C5 O51 177.10(19) ?
O61 C6 C5 C4 179.33(19) ?
C7 C6 C5 C4 1.1(3) ?
O51 C5 C4 O41 3.2(3) ?
C6 C5 C4 O41 179.3(2) ?
O51 C5 C4 C3 -178.34(19) ?
C6 C5 C4 C3 -2.3(3) ?
O41 C4 C3 C2 179.8(2) ?
C5 C4 C3 C2 1.5(3) ?
C4 C3 C2 C7 .5(3) ?
C4 C3 C2 C1 -177.34(18) ?
C6 C7 C2 C3 -1.7(3) ?
C8 C7 C2 C3 177.80(18) ?
C6 C7 C2 C1 175.99(17) ?
C8 C7 C2 C1 -4.5(3) y
C3 C2 C1 N11 -108.72(18) ?
C7 C2 C1 N11 73.5(2) y
C3 C2 C1 C12 129.79(18) ?
C7 C2 C1 C12 -48.0(2) y
N11 C1 C12 C13 -45.9(2) y
C2 C1 C12 C13 75.2(2) y
C1 C12 C13 C9 -5.4(3) y
C12 C13 C9 O91 160.46(17) ?
C12 C13 C9 O10 39.8(2) y
C12 C13 C9 C8 -77.3(2) y
O91 C9 O10 N11 -141.62(14) ?
C13 C9 O10 N11 -20.2(2) y
C8 C9 O10 N11 96.12(16) y
C9 O10 N11 C1' 96.91(17) ?
C9 O10 N11 C1 -28.98(18) y
C12 C1 N11 O10 62.14(17) y
C2 C1 N11 O10 -61.90(17) y
C12 C1 N11 C1' -62.15(18) ?
C2 C1 N11 C1' 173.80(14) ?
O10 N11 C1' C6' -17.4(2) ?
C1 N11 C1' C6' 105.3(2) ?
O10 N11 C1' C2' 159.78(16) ?
C1 N11 C1' C2' -77.5(2) ?
C6' C1' C2' C3' -.5(3) ?
N11 C1' C2' C3' -177.83(19) ?
C1' C2' C3' C4' .6(3) ?
C2' C3' C4' C5' -.5(4) ?
C3' C4' C5' C6' .3(4) ?
C2' C1' C6' C5' .3(3) ?
N11 C1' C6' C5' 177.4(2) ?
C4' C5' C6' C1' -.2(4) ?
C2 C7 C8 O81 165.3(2) ?
C6 C7 C8 O81 -15.2(3) ?
C2 C7 C8 C9 -11.4(3) y
C6 C7 C8 C9 168.09(17) ?
O91 C9 C8 O81 17.2(3) ?
O10 C9 C8 O81 135.80(19) ?
C13 C9 C8 O81 -102.2(2) ?
O91 C9 C8 C7 -165.87(16) ?
O10 C9 C8 C7 -47.3(2) y
C13 C9 C8 C7 74.7(2) y
C5 C6 O61 C61 90.1(2) ?
C7 C6 O61 C61 -91.7(2) ?
C6 C5 O51 C51 85.4(3) ?
C4 C5 O51 C51 -98.5(3) ?
C5 C4 O41 C41 -161.8(2) ?
C3 C4 O41 C41 19.9(3) ?
O10 C9 O91 C91 -49.9(2) ?
C13 C9 O91 C91 -174.48(16) ?
C8 C9 O91 C91 68.2(2) ?
