#------------------------------------------------------------------------------
#$Date: 2016-03-26 17:06:22 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180374 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/43/7204319.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7204319
loop_
_publ_author_name
'Sugahara, Masakatsu'
'Moritani, Yasunori'
'Kuroda, Tooru'
'Kondo, Kazuhiko'
'Ukita, Tatsuzo'
_publ_section_title
;
 Synthetic and mechanistic study of the acid-promoted aromatisation of
 the Diels--Alder adduct:
 6,7-dimethoxy-1-(4-pyridyl)-1,4-epoxytetrahydronaphthalene-2,3-dicarboxylate
;
_journal_issue                   6
_journal_name_full
'Journal of the Chemical Society, Perkin Transactions 1'
_journal_page_first              768
_journal_paper_doi               10.1039/b110265f
_journal_year                    2002
_chemical_formula_sum            'C21 H21 N O7'
_chemical_formula_weight         399.39
_chemical_name_systematic
; 
1,4-Epoxynaphthalene-2,3-dicarboxylic acid, 1-(4-pyridyl)-
1,2,3,4-tetrahydro-6,7-dimethoxy-, dimethyl ester, (1beta, 2beta ,
3alpha , 4beta)-rel- (9CI)
;
_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'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 98.84(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.529(2)
_cell_length_b                   13.759(1)
_cell_length_c                   16.822(1)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293
_cell_measurement_theta_max      45
_cell_measurement_theta_min      35
_cell_volume                     1950.6(5)
_computing_cell_refinement       'Rigaku/MSC AFC5R software 1992'
_computing_data_collection       'Rigaku/MSC AFC5R software 1992'
_computing_data_reduction        'Rigaku/MSC AFC5R software 1992'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Rigaku AFC5R diffractometer'
_diffrn_measurement_method       ot
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'nomal-focus rotating anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0209
_diffrn_reflns_av_sigmaI/netI    0.0168
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       16
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       19
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            3562
_diffrn_reflns_theta_full        65.06
_diffrn_reflns_theta_max         65.06
_diffrn_reflns_theta_min         4.17
_diffrn_standards_decay_%        0.0
_diffrn_standards_interval_count 200
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.862
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.360
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.3
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.241
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.038
_refine_ls_extinction_coef       0.0021(6)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.317
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         3322
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.317
_refine_ls_R_factor_all          0.0564
_refine_ls_R_factor_gt           0.0474
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.1000P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1634
_refine_ls_wR_factor_ref         0.1715
_reflns_number_gt                2785
_reflns_number_total             3322
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b110265f.txt
_cod_data_source_block           compound3
_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 
;
_cod_original_cell_volume        1950.7(4)
_cod_original_sg_symbol_H-M      P21/n
_cod_database_code               7204319
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_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
O11 O -0.77204(17) 0.32912(11) -0.27042(8) 0.0540(4) Uani 1 1 d . . .
O13 O -1.2199(2) 0.27692(13) -0.44070(10) 0.0745(5) Uani 1 1 d . . .
O14 O -1.22050(18) 0.19228(13) -0.32820(9) 0.0655(5) Uani 1 1 d . . .
O17 O -0.9738(2) 0.51414(13) -0.26490(11) 0.0798(5) Uani 1 1 d . . .
O18 O -0.9999(2) 0.56434(12) -0.39248(11) 0.0696(5) Uani 1 1 d . . .
O26 O -0.6817(2) 0.10661(12) -0.55722(10) 0.0749(5) Uani 1 1 d . . .
O28 O -0.8009(2) -0.01842(10) -0.47154(9) 0.0613(4) Uani 1 1 d . . .
N23 N -0.4272(3) 0.57788(18) -0.37844(18) 0.0862(7) Uani 1 1 d . . .
C1 C -0.8942(2) 0.25639(15) -0.28474(11) 0.0503(5) Uani 1 1 d . . .
C2 C -1.0392(2) 0.31932(15) -0.32160(12) 0.0496(5) Uani 1 1 d . . .
C3 C -0.9610(2) 0.39684(15) -0.36909(11) 0.0478(5) Uani 1 1 d . . .
C4 C -0.7824(2) 0.36257(15) -0.35250(11) 0.0476(5) Uani 1 1 d . . .
C5 C -0.7739(2) 0.26653(14) -0.39689(12) 0.0465(5) Uani 1 1 d . . .
C6 C -0.7203(2) 0.24080(15) -0.46758(12) 0.0484(5) Uani 1 1 d . . .
C7 C -0.7322(2) 0.14375(15) -0.49042(12) 0.0497(5) Uani 1 1 d . . .
C8 C -0.7987(2) 0.07431(14) -0.44352(12) 0.0487(5) Uani 1 1 d . . .
C9 C -0.8566(2) 0.10233(15) -0.37428(12) 0.0495(5) Uani 1 1 d . . .
C10 C -0.8414(2) 0.19850(15) -0.35196(11) 0.0485(5) Uani 1 1 d . . .
C12 C -1.1692(2) 0.26207(16) -0.37177(12) 0.0515(5) Uani 1 1 d . . .
C15 C -1.3446(3) 0.1306(2) -0.36870(16) 0.0778(8) Uani 1 1 d . . .
C16 C -0.9790(2) 0.49658(16) -0.33492(13) 0.0552(5) Uani 1 1 d . . .
C19 C -1.0073(4) 0.6632(2) -0.3639(2) 0.0943(10) Uani 1 1 d . . .
C20 C -0.6576(2) 0.43682(15) -0.36145(13) 0.0524(5) Uani 1 1 d . . .
C21 C -0.6745(3) 0.50018(18) -0.42592(15) 0.0662(6) Uani 1 1 d . . .
C22 C -0.5569(3) 0.5688(2) -0.4308(2) 0.0804(8) Uani 1 1 d . . .
C24 C -0.4103(3) 0.5156(2) -0.3178(2) 0.0838(8) Uani 1 1 d . . .
C25 C -0.5206(3) 0.44436(19) -0.30586(16) 0.0680(6) Uani 1 1 d . . .
C27 C -0.5775(4) 0.1623(2) -0.59549(17) 0.0811(8) Uani 1 1 d . . .
C29 C -0.8535(3) -0.09215(16) -0.42247(15) 0.0664(6) Uani 1 1 d . . .
H30 H -0.9091 0.2187 -0.2391 0.061 Uiso 1 1 d . . .
H31 H -1.0810 0.3501 -0.2792 0.057 Uiso 1 1 d . . .
H32 H -1.0023 0.3943 -0.4247 0.055 Uiso 1 1 d . . .
H33 H -0.6761 0.2875 -0.4987 0.056 Uiso 1 1 d . . .
H34 H -0.9060 0.0570 -0.3441 0.056 Uiso 1 1 d . . .
H35 H -1.4304 0.1702 -0.3946 0.078 Uiso 1 1 d . . .
H36 H -1.3828 0.0888 -0.3301 0.078 Uiso 1 1 d . . .
H37 H -1.3037 0.0920 -0.4083 0.078 Uiso 1 1 d . . .
H38 H -1.1035 0.6724 -0.3419 0.094 Uiso 1 1 d . . .
H39 H -1.0053 0.7075 -0.4080 0.094 Uiso 1 1 d . . .
H40 H -0.9178 0.6756 -0.3231 0.094 Uiso 1 1 d . . .
H41 H -0.7663 0.4981 -0.4660 0.079 Uiso 1 1 d . . .
H42 H -0.5720 0.6134 -0.4735 0.096 Uiso 1 1 d . . .
H43 H -0.3145 0.5178 -0.2788 0.100 Uiso 1 1 d . . .
H44 H -0.5029 0.4027 -0.2601 0.079 Uiso 1 1 d . . .
H45 H -0.4941 0.1846 -0.5557 0.105 Uiso 1 1 d . . .
H46 H -0.5340 0.1209 -0.6322 0.105 Uiso 1 1 d . . .
H47 H -0.6320 0.2140 -0.6226 0.105 Uiso 1 1 d . . .
H48 H -0.7918 -0.0892 -0.3702 0.083 Uiso 1 1 d . . .
H49 H -0.8413 -0.1537 -0.4455 0.083 Uiso 1 1 d . . .
H50 H -0.9619 -0.0813 -0.4181 0.083 Uiso 1 1 d . . .
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'
O O 0.0492 0.0322 '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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O11 C4 97.19(13) . . ?
C12 O14 C15 116.53(17) . . ?
C16 O18 C19 115.0(2) . . ?
C7 O26 C27 118.46(18) . . ?
C8 O28 C29 117.18(16) . . ?
C22 N23 C24 116.0(2) . . ?
O11 C1 C10 101.59(15) . . ?
O11 C1 C2 100.96(16) . . ?
C10 C1 C2 107.79(16) . . ?
C12 C2 C3 114.21(17) . . ?
C12 C2 C1 113.75(17) . . ?
C3 C2 C1 102.15(15) . . ?
C16 C3 C2 110.79(16) . . ?
C16 C3 C4 110.92(16) . . ?
C2 C3 C4 100.60(15) . . ?
O11 C4 C20 111.88(16) . . ?
O11 C4 C5 101.03(15) . . ?
C20 C4 C5 116.96(16) . . ?
O11 C4 C3 100.36(14) . . ?
C20 C4 C3 117.36(17) . . ?
C5 C4 C3 106.83(15) . . ?
C10 C5 C6 121.11(18) . . ?
C10 C5 C4 105.30(16) . . ?
C6 C5 C4 133.56(18) . . ?
C5 C6 C7 117.63(17) . . ?
O26 C7 C6 124.71(18) . . ?
O26 C7 C8 114.32(18) . . ?
C6 C7 C8 120.96(18) . . ?
O28 C8 C9 124.33(18) . . ?
O28 C8 C7 115.25(17) . . ?
C9 C8 C7 120.42(18) . . ?
C10 C9 C8 117.71(18) . . ?
C9 C10 C5 122.12(18) . . ?
C9 C10 C1 133.31(18) . . ?
C5 C10 C1 104.46(17) . . ?
O13 C12 O14 124.2(2) . . ?
O13 C12 C2 125.51(19) . . ?
O14 C12 C2 110.28(17) . . ?
O17 C16 O18 123.6(2) . . ?
O17 C16 C3 124.7(2) . . ?
O18 C16 C3 111.69(18) . . ?
C21 C20 C25 117.3(2) . . ?
C21 C20 C4 121.25(19) . . ?
C25 C20 C4 121.5(2) . . ?
C20 C21 C22 119.1(2) . . ?
N23 C22 C21 124.6(3) . . ?
N23 C24 C25 124.8(3) . . ?
C20 C25 C24 118.3(3) . . ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O11 C1 1.438(2) . ?
O11 C4 1.445(2) . ?
O13 C12 1.191(3) . ?
O14 C12 1.323(2) . ?
O14 C15 1.444(3) . ?
O17 C16 1.196(3) . ?
O18 C16 1.336(3) . ?
O18 C19 1.448(3) . ?
O26 C7 1.363(2) . ?
O26 C27 1.402(3) . ?
O28 C8 1.359(2) . ?
O28 C29 1.423(3) . ?
N23 C22 1.310(4) . ?
N23 C24 1.324(4) . ?
C1 C10 1.508(3) . ?
C1 C2 1.558(3) . ?
C2 C12 1.508(3) . ?
C2 C3 1.544(3) . ?
C3 C16 1.505(3) . ?
C3 C4 1.578(3) . ?
C4 C20 1.500(3) . ?
C4 C5 1.525(3) . ?
C5 C10 1.383(3) . ?
C5 C6 1.384(3) . ?
C6 C7 1.389(3) . ?
C7 C8 1.412(3) . ?
C8 C9 1.388(3) . ?
C9 C10 1.376(3) . ?
C20 C21 1.382(3) . ?
C20 C25 1.384(3) . ?
C21 C22 1.389(3) . ?
C24 C25 1.394(4) . ?
