#------------------------------------------------------------------------------
#$Date: 2016-03-26 17:06:22 +0200 (Sat, 26 Mar 2016) $
#$Revision: 180374 $
#$URL: svn://www.crystallography.net/cod/cif/7/20/43/7204317.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_7204317
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 ,
3beta , 4beta)-rel- (9CI)
;
_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'
_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                 109.87(1)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.159(2)
_cell_length_b                   16.895(1)
_cell_length_c                   13.252(1)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293
_cell_measurement_theta_max      45
_cell_measurement_theta_min      35
_cell_volume                     1928.5(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  0.0141
_diffrn_reflns_av_sigmaI/netI    0.0138
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            3515
_diffrn_reflns_theta_full        65.08
_diffrn_reflns_theta_max         65.08
_diffrn_reflns_theta_min         4.41
_diffrn_standards_decay_%        0.0
_diffrn_standards_interval_count 200
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.872
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.375
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             840
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.2
_refine_diff_density_max         0.671
_refine_diff_density_min         -0.346
_refine_diff_density_rms         0.039
_refine_ls_extinction_coef       0.0026(7)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.450
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     263
_refine_ls_number_reflns         3296
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.450
_refine_ls_R_factor_all          0.0523
_refine_ls_R_factor_gt           0.0462
_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          0.1726
_refine_ls_wR_factor_ref         0.1786
_reflns_number_gt                2914
_reflns_number_total             3296
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b110265f.txt
_cod_data_source_block           compound1
_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        1928.6(4)
_cod_original_sg_symbol_H-M      P21/c
_cod_database_code               7204317
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_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 0.37267(15) 0.23412(7) 0.66595(11) 0.0437(4) Uani 1 1 d . . .
O13 O 0.6412(2) 0.35990(9) 0.69864(16) 0.0687(5) Uani 1 1 d . . .
O14 O 0.84551(17) 0.28195(10) 0.77219(16) 0.0667(5) Uani 1 1 d . . .
O17 O 0.6358(2) 0.23225(11) 0.90295(14) 0.0710(5) Uani 1 1 d . . .
O18 O 0.78849(18) 0.12902(10) 0.90462(12) 0.0598(4) Uani 1 1 d . . .
O26 O 0.23634(18) -0.06810(8) 0.43814(13) 0.0556(4) Uani 1 1 d . . .
O28 O 0.28008(19) 0.02898(8) 0.29153(12) 0.0558(4) Uani 1 1 d . . .
N23 N 0.1981(3) 0.07959(15) 0.92872(17) 0.0703(6) Uani 1 1 d . . .
C1 C 0.4501(2) 0.23486(11) 0.58763(16) 0.0438(5) Uani 1 1 d . . .
C2 C 0.6198(2) 0.21980(11) 0.66023(16) 0.0433(5) Uani 1 1 d . . .
C3 C 0.5976(2) 0.15713(11) 0.74076(16) 0.0410(4) Uani 1 1 d . . .
C4 C 0.4144(2) 0.15441(11) 0.70403(15) 0.0399(5) Uani 1 1 d . . .
C5 C 0.3647(2) 0.10863(11) 0.59895(15) 0.0408(4) Uani 1 1 d . . .
C6 C 0.3147(2) 0.03172(11) 0.57210(16) 0.0415(4) Uani 1 1 d . . .
C7 C 0.2856(2) 0.00813(11) 0.46726(16) 0.0422(5) Uani 1 1 d . . .
C8 C 0.3125(2) 0.05948(12) 0.39158(15) 0.0428(5) Uani 1 1 d . . .
C9 C 0.3680(2) 0.13604(11) 0.42106(16) 0.0438(5) Uani 1 1 d . . .
C10 C 0.3894(2) 0.15987(11) 0.52486(15) 0.0414(4) Uani 1 1 d . . .
C12 C 0.6988(2) 0.29558(12) 0.71183(18) 0.0496(5) Uani 1 1 d . . .
C15 C 0.9289(4) 0.34977(19) 0.8315(3) 0.0986(12) Uani 1 1 d . . .
C16 C 0.6727(2) 0.17885(12) 0.85769(17) 0.0468(5) Uani 1 1 d . . .
C19 C 0.8765(3) 0.1436(2) 1.0152(2) 0.0821(9) Uani 1 1 d . . .
C20 C 0.3421(2) 0.13004(11) 0.78474(15) 0.0420(5) Uani 1 1 d . . .
C21 C 0.3864(3) 0.06048(15) 0.8422(2) 0.0597(6) Uani 1 1 d . . .
C22 C 0.3118(3) 0.03887(16) 0.9130(2) 0.0692(7) Uani 1 1 d . . .
C24 C 0.1579(3) 0.14533(17) 0.8734(2) 0.0677(7) Uani 1 1 d . . .
C25 C 0.2244(2) 0.17302(13) 0.80136(18) 0.0523(5) Uani 1 1 d . . .
C27 C 0.0825(4) -0.07712(18) 0.3775(3) 0.0868(9) Uani 1 1 d . . .
C29 C 0.2881(3) 0.07937(15) 0.2089(2) 0.0662(7) Uani 1 1 d . . .
H30 H 0.4361 0.2816 0.5458 0.052 Uiso 1 1 d . . .
H31 H 0.6758 0.1968 0.6191 0.051 Uiso 1 1 d . . .
H32 H 0.6354 0.1074 0.7280 0.049 Uiso 1 1 d . . .
H33 H 0.3011 -0.0037 0.6240 0.050 Uiso 1 1 d . . .
H34 H 0.3901 0.1707 0.3719 0.052 Uiso 1 1 d . . .
H35 H 0.9267 0.3915 0.7830 0.117 Uiso 1 1 d . . .
H36 H 1.0337 0.3352 0.8692 0.117 Uiso 1 1 d . . .
H37 H 0.8814 0.3667 0.8812 0.117 Uiso 1 1 d . . .
H38 H 0.9257 0.1937 1.0219 0.098 Uiso 1 1 d . . .
H39 H 0.9530 0.1035 1.0407 0.098 Uiso 1 1 d . . .
H40 H 0.8092 0.1431 1.0561 0.098 Uiso 1 1 d . . .
H41 H 0.4674 0.0290 0.8335 0.071 Uiso 1 1 d . . .
H42 H 0.3448 -0.0091 0.9518 0.082 Uiso 1 1 d . . .
H43 H 0.0768 0.1761 0.8829 0.084 Uiso 1 1 d . . .
H44 H 0.1895 0.2206 0.7628 0.064 Uiso 1 1 d . . .
H45 H 0.0631 -0.0541 0.3090 0.103 Uiso 1 1 d . . .
H46 H 0.0574 -0.1319 0.3696 0.103 Uiso 1 1 d . . .
H47 H 0.0201 -0.0517 0.4125 0.103 Uiso 1 1 d . . .
H48 H 0.2254 0.1247 0.2055 0.079 Uiso 1 1 d . . .
H49 H 0.2515 0.0520 0.1423 0.079 Uiso 1 1 d . . .
H50 H 0.3926 0.0953 0.2229 0.079 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 97.08(13) . . ?
C12 O14 C15 115.3(2) . . ?
C16 O18 C19 116.8(2) . . ?
C27 O26 C7 116.21(19) . . ?
C8 O28 C29 118.55(17) . . ?
C24 N23 C22 116.0(2) . . ?
O11 C1 C10 102.09(14) . . ?
O11 C1 C2 100.77(15) . . ?
C10 C1 C2 107.94(15) . . ?
C12 C2 C1 111.51(16) . . ?
C12 C2 C3 114.64(17) . . ?
C1 C2 C3 101.50(15) . . ?
C16 C3 C2 114.54(16) . . ?
C16 C3 C4 112.87(15) . . ?
C2 C3 C4 100.37(15) . . ?
O11 C4 C20 112.23(15) . . ?
O11 C4 C5 101.14(14) . . ?
C20 C4 C5 116.59(15) . . ?
O11 C4 C3 101.99(14) . . ?
C20 C4 C3 118.01(15) . . ?
C5 C4 C3 104.63(14) . . ?
C6 C5 C10 121.64(18) . . ?
C6 C5 C4 133.08(17) . . ?
C10 C5 C4 105.13(16) . . ?
C7 C6 C5 117.62(18) . . ?
O26 C7 C6 119.00(18) . . ?
O26 C7 C8 119.78(17) . . ?
C6 C7 C8 121.15(17) . . ?
O28 C8 C9 124.24(18) . . ?
O28 C8 C7 115.34(17) . . ?
C9 C8 C7 120.42(17) . . ?
C10 C9 C8 117.60(17) . . ?
C9 C10 C5 121.46(17) . . ?
C9 C10 C1 133.79(17) . . ?
C5 C10 C1 104.59(16) . . ?
O13 C12 O14 123.45(19) . . ?
O13 C12 C2 125.71(19) . . ?
O14 C12 C2 110.79(17) . . ?
O17 C16 O18 124.0(2) . . ?
O17 C16 C3 126.19(19) . . ?
O18 C16 C3 109.78(16) . . ?
C25 C20 C21 117.29(19) . . ?
C25 C20 C4 122.02(18) . . ?
C21 C20 C4 120.62(18) . . ?
C20 C21 C22 118.5(2) . . ?
N23 C22 C21 124.5(2) . . ?
N23 C24 C25 124.7(2) . . ?
C24 C25 C20 119.1(2) . . ?
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 1.442(2) . ?
O11 C4 1.443(2) . ?
O13 C12 1.194(3) . ?
O14 C12 1.330(3) . ?
O14 C15 1.452(3) . ?
O17 C16 1.194(3) . ?
O18 C16 1.331(3) . ?
O18 C19 1.434(3) . ?
O26 C27 1.373(3) . ?
O26 C7 1.376(2) . ?
O28 C8 1.358(2) . ?
O28 C29 1.409(3) . ?
N23 C24 1.313(3) . ?
N23 C22 1.322(4) . ?
C1 C10 1.514(3) . ?
C1 C2 1.546(3) . ?
C2 C12 1.515(3) . ?
C2 C3 1.565(3) . ?
C3 C16 1.511(3) . ?
C3 C4 1.581(2) . ?
C4 C20 1.494(3) . ?
C4 C5 1.521(3) . ?
C5 C6 1.383(3) . ?
C5 C10 1.384(3) . ?
C6 C7 1.382(3) . ?
C7 C8 1.409(3) . ?
C8 C9 1.396(3) . ?
C9 C10 1.382(3) . ?
C20 C25 1.378(3) . ?
C20 C21 1.384(3) . ?
C21 C22 1.384(3) . ?
C24 C25 1.377(3) . ?
