#------------------------------------------------------------------------------
#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/23/4022320.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_4022320
loop_
_publ_author_name
'Masami Sakamoto'
'Takeru Sano'
'Shohei Fujita'
'Masaru Ando'
'Kentaro Yamaguchi'
'Takashi Mino'
'Tsutomu Fujita'
_publ_section_title
;
 Regioselective Photocycloaddition of Pyridine Derivatives
 to Electron-Rich Alkenes
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              1447
_journal_page_last               1450
_journal_paper_doi               10.1021/jo0266285
_journal_volume                  68
_journal_year                    2003
_chemical_formula_moiety         'C13 H18 N2 O3 '
_chemical_formula_sum            'C13 H18 N2 O3'
_chemical_formula_weight         250.30
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_audit_creation_date             'Thu Jan 17 20:29:13 2002'
_audit_creation_method           'by teXsan'
_cell_angle_alpha                90
_cell_angle_beta                 93.629(9)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.184(1)
_cell_length_b                   11.459(1)
_cell_length_c                   11.709(1)
_cell_measurement_temperature    273.2
_cell_measurement_theta_max      140
_cell_measurement_theta_min      3
_cell_volume                     1363.8(3)
_computing_cell_refinement       'MSC/AFC Diffractometer Control'
_computing_data_collection       'MSC/AFC Diffractometer Control'
_computing_data_reduction        'teXsan Ver. 1.10'
_computing_publication_material  'teXsan Ver. 1.10'
_computing_structure_refinement  'teXsan Ver. 1.10'
_computing_structure_solution    DirectMethod
_diffrn_measurement_device_type  'Rigaku AFC5S'
_diffrn_radiation_type           'Cu Ka'
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  0.135
_diffrn_reflns_limit_h_max       0
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       0
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       0
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2747
_diffrn_standards_decay_%        0.12
_diffrn_standards_interval_count 0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.717
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.509
_exptl_absorpt_correction_type   refdelf
_exptl_absorpt_process_details   '(Walker & Stuart, 1983)'
_exptl_crystal_colour            unknown
_exptl_crystal_density_diffrn    1.219
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       unknown
_exptl_crystal_size_max          0.000
_exptl_crystal_size_mid          0.000
_exptl_crystal_size_min          0.000
_refine_diff_density_max         0.45
_refine_diff_density_min         -0.34
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   6.090
_refine_ls_hydrogen_treatment    refall
_refine_ls_number_parameters     235
_refine_ls_number_reflns         1850
_refine_ls_R_factor_gt           0.0000
_refine_ls_shift/su_max          4.9990
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     'w = 1/[s²(Fo) + 0.00000|Fo|²]'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0810
_reflns_number_gt                0
_reflns_number_total             0
_reflns_threshold_expression     F²>2.0s(F²)
_cod_data_source_file            jo0266285si20030206_113355.cif
_cod_data_source_block           Kentax_Sakamoto_94-09-05
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_original_formula_sum        'C13 H18 N2 O3 '
_cod_database_code               4022320
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
1/2-x,1/2+y,1/2-z
-x,-y,-z
1/2+x,1/2-y,1/2+z
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_calc_flag
O(1) O 0.4256(3) -0.3329(3) 0.7308(3) 0.055(1) Uani 1.00 d
O(2) O 0.5218(3) 0.1104(2) 0.6064(2) 0.0477(9) Uani 1.00 d
O(3) O 0.7027(3) -0.0563(3) 0.6046(3) 0.0500(9) Uani 1.00 d
N(1) N 0.5798(3) -0.1907(3) 0.6938(3) 0.045(1) Uani 1.00 d
N(2) N 0.1257(4) -0.2335(4) 0.6679(4) 0.071(2) Uani 1.00 d
C(1) C 0.3659(4) -0.0260(4) 0.6667(4) 0.042(1) Uani 1.00 d
C(2) C 0.5073(4) 0.0153(4) 0.6823(4) 0.042(1) Uani 1.00 d
C(3) C 0.5971(4) -0.0863(4) 0.6618(4) 0.042(1) Uani 1.00 d
C(4) C 0.4669(4) -0.2171(4) 0.7554(4) 0.043(1) Uani 1.00 d
C(5) C 0.3437(4) -0.1325(4) 0.7396(4) 0.040(1) Uani 1.00 d
C(6) C 0.3669(5) -0.1145(4) 0.8700(4) 0.049(1) Uani 1.00 d
C(7) C 0.4702(5) -0.1828(4) 0.8812(4) 0.051(1) Uani 1.00 d
C(8) C 0.2931(8) -0.0378(7) 0.9472(6) 0.071(2) Uani 1.00 d
C(9) C 0.5204(8) -0.4194(6) 0.7645(9) 0.081(3) Uani 1.00 d
C(10) C 0.7806(7) -0.1498(6) 0.5654(7) 0.070(2) Uani 1.00 d
C(11) C 0.6191(8) 0.1940(6) 0.6434(7) 0.073(2) Uani 1.00 d
C(12) C 0.6037(10) 0.3024(6) 0.5799(8) 0.083(3) Uani 1.00 d
C(13) C 0.2210(5) -0.1900(4) 0.7020(4) 0.047(1) Uani 1.00 d
H(5) H 0.607(7) 0.215(7) 0.728(7) 0.18(4) Uiso 1.00 calc
H(6) H 0.689(6) 0.171(6) 0.633(6) 0.13(3) Uiso 1.00 calc
H(7) H 0.375(8) 0.021(8) 1.002(8) 0.24(4) Uiso 1.00 calc
H(8) H 0.224(8) -0.019(8) 0.921(7) 0.17(4) Uiso 1.00 calc
H(9) H 0.298(7) -0.079(6) 1.013(6) 0.15(3) Uiso 1.00 calc
H(10) H 0.469(5) -0.497(6) 0.738(5) 0.10(2) Uiso 1.00 calc
H(11) H 0.595(6) -0.410(5) 0.714(5) 0.10(2) Uiso 1.00 calc
H(12) H 0.529(5) -0.413(5) 0.831(4) 0.06(2) Uiso 1.00 calc
H(13) H 0.810(6) -0.199(5) 0.626(6) 0.13(3) Uiso 1.00 calc
H(14) H 0.719(6) -0.208(5) 0.517(5) 0.12(3) Uiso 1.00 calc
H(15) H 0.844(5) -0.123(4) 0.529(4) 0.06(2) Uiso 1.00 calc
H(16) H 0.676(5) 0.361(4) 0.611(4) 0.08(2) Uiso 1.00 calc
H(17) H 0.611(6) 0.286(5) 0.500(6) 0.13(3) Uiso 1.00 calc
H(18) H 0.539(6) 0.336(5) 0.599(5) 0.10(3) Uiso 1.00 calc
H(21) H 0.307(4) 0.038(3) 0.688(3) 0.04(1) Uiso 1.00 calc
H(22) H 0.348(4) -0.044(3) 0.586(3) 0.04(1) Uiso 1.00 calc
H(23) H 0.523(4) 0.037(3) 0.764(3) 0.05(1) Uiso 1.00 calc
H(25) H 0.530(5) -0.200(4) 0.943(4) 0.08(2) Uiso 1.00 calc
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.018 0.009
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
H H 0.000 0.000
;International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.2)
;
N N 0.031 0.018
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
O O 0.049 0.032
;International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.1)
;
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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C(4) O(1) C(9) 114.2(4) 0_555 0_555 yes
C(2) O(2) C(11) 115.0(4) 0_555 0_555 yes
C(3) O(3) C(10) 116.5(4) 0_555 0_555 yes
C(3) N(1) C(4) 118.7(4) 0_555 0_555 yes
C(2) C(1) C(5) 111.0(4) 0_555 0_555 yes
O(2) C(2) C(1) 107.5(4) 0_555 0_555 yes
O(2) C(2) C(3) 113.8(4) 0_555 0_555 yes
C(1) C(2) C(3) 108.7(4) 0_555 0_555 yes
O(3) C(3) N(1) 121.2(4) 0_555 0_555 yes
O(3) C(3) C(2) 113.2(4) 0_555 0_555 yes
N(1) C(3) C(2) 125.7(4) 0_555 0_555 yes
O(1) C(4) N(1) 109.5(4) 0_555 0_555 yes
O(1) C(4) C(5) 109.1(3) 0_555 0_555 yes
O(1) C(4) C(7) 115.2(4) 0_555 0_555 yes
N(1) C(4) C(5) 117.9(4) 0_555 0_555 yes
N(1) C(4) C(7) 117.7(4) 0_555 0_555 yes
C(5) C(4) C(7) 85.6(3) 0_555 0_555 yes
C(1) C(5) C(4) 114.4(4) 0_555 0_555 yes
C(1) C(5) C(6) 115.5(4) 0_555 0_555 yes
C(1) C(5) C(13) 110.5(4) 0_555 0_555 yes
C(4) C(5) C(6) 84.1(3) 0_555 0_555 yes
C(4) C(5) C(13) 114.6(4) 0_555 0_555 yes
C(6) C(5) C(13) 115.7(4) 0_555 0_555 yes
C(5) C(6) C(7) 95.2(4) 0_555 0_555 yes
C(5) C(6) C(8) 128.7(5) 0_555 0_555 yes
C(7) C(6) C(8) 136.1(5) 0_555 0_555 yes
C(4) C(7) C(6) 95.1(4) 0_555 0_555 yes
O(2) C(11) C(12) 111.6(6) 0_555 0_555 yes
N(2) C(13) C(5) 177.1(5) 0_555 0_555 yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O(1) C(4) 1.416(5) yes
O(1) C(9) 1.421(7) yes
O(2) C(2) 1.419(5) yes
O(2) C(11) 1.426(6) yes
O(3) C(3) 1.347(5) yes
O(3) C(10) 1.426(6) yes
N(1) C(3) 1.269(5) yes
N(1) C(4) 1.427(5) yes
N(2) C(13) 1.140(5) yes
C(1) C(2) 1.516(6) yes
C(1) C(5) 1.515(6) yes
C(2) C(3) 1.510(6) yes
C(4) C(5) 1.587(6) yes
C(4) C(7) 1.523(6) yes
C(5) C(6) 1.544(6) yes
C(5) C(13) 1.456(6) yes
C(6) C(7) 1.312(6) yes
C(6) C(8) 1.496(8) yes
C(11) C(12) 1.452(9) yes
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O(1) C(4) N(1) C(3) 148.9(4) 1_555 1_555 1_555 1_555 yes
O(1) C(4) C(5) C(1) -130.5(4) 1_555 1_555 1_555 1_555 yes
O(1) C(4) C(5) C(6) 114.2(4) 1_555 1_555 1_555 1_555 yes
O(1) C(4) C(5) C(13) -1.4(5) 1_555 1_555 1_555 1_555 yes
O(1) C(4) C(7) C(6) -107.8(4) 1_555 1_555 1_555 1_555 yes
O(2) C(2) C(1) C(5) 176.5(4) 1_555 1_555 1_555 1_555 yes
O(2) C(2) C(3) O(3) 21.2(5) 1_555 1_555 1_555 1_555 yes
O(2) C(2) C(3) N(1) -159.2(4) 1_555 1_555 1_555 1_555 yes
O(3) C(3) N(1) C(4) 179.2(4) 1_555 1_555 1_555 1_555 yes
O(3) C(3) C(2) C(1) 140.9(4) 1_555 1_555 1_555 1_555 yes
N(1) C(3) O(3) C(10) 10.4(7) 1_555 1_555 1_555 1_555 yes
N(1) C(3) C(2) C(1) -39.5(6) 1_555 1_555 1_555 1_555 yes
N(1) C(4) O(1) C(9) 62.0(6) 1_555 1_555 1_555 1_555 yes
N(1) C(4) C(5) C(1) -4.8(6) 1_555 1_555 1_555 1_555 yes
N(1) C(4) C(5) C(6) -120.2(4) 1_555 1_555 1_555 1_555 yes
N(1) C(4) C(5) C(13) 124.2(4) 1_555 1_555 1_555 1_555 yes
N(1) C(4) C(7) C(6) 120.6(4) 1_555 1_555 1_555 1_555 yes
N(2) C(13) C(5) C(1) 32(10) 1_555 1_555 1_555 1_555 yes
N(2) C(13) C(5) C(4) -99(10) 1_555 1_555 1_555 1_555 yes
N(2) C(13) C(5) C(6) 165(10) 1_555 1_555 1_555 1_555 yes
C(1) C(2) O(2) C(11) 151.0(5) 1_555 1_555 1_555 1_555 yes
C(1) C(5) C(4) C(7) 114.3(4) 1_555 1_555 1_555 1_555 yes
C(1) C(5) C(6) C(7) -113.0(4) 1_555 1_555 1_555 1_555 yes
C(1) C(5) C(6) C(8) 64.5(7) 1_555 1_555 1_555 1_555 yes
C(2) O(2) C(11) C(12) -164.0(7) 1_555 1_555 1_555 1_555 yes
C(2) C(1) C(5) C(4) -33.5(5) 1_555 1_555 1_555 1_555 yes
C(2) C(1) C(5) C(6) 61.7(5) 1_555 1_555 1_555 1_555 yes
C(2) C(1) C(5) C(13) -164.6(4) 1_555 1_555 1_555 1_555 yes
C(2) C(3) O(3) C(10) -170.0(5) 1_555 1_555 1_555 1_555 yes
C(2) C(3) N(1) C(4) -0.3(7) 1_555 1_555 1_555 1_555 yes
C(3) N(1) C(4) C(5) 23.4(6) 1_555 1_555 1_555 1_555 yes
C(3) N(1) C(4) C(7) -77.0(5) 1_555 1_555 1_555 1_555 yes
C(3) C(2) O(2) C(11) -88.6(6) 1_555 1_555 1_555 1_555 yes
C(3) C(2) C(1) C(5) 52.9(5) 1_555 1_555 1_555 1_555 yes
C(4) C(5) C(6) C(7) 1.2(4) 1_555 1_555 1_555 1_555 yes
C(4) C(5) C(6) C(8) 178.7(6) 1_555 1_555 1_555 1_555 yes
C(4) C(7) C(6) C(5) -1.3(4) 1_555 1_555 1_555 1_555 yes
C(4) C(7) C(6) C(8) -178.5(6) 1_555 1_555 1_555 1_555 yes
C(5) C(4) O(1) C(9) -167.6(6) 1_555 1_555 1_555 1_555 yes
C(5) C(4) C(7) C(6) 1.2(4) 1_555 1_555 1_555 1_555 yes
C(6) C(5) C(4) C(7) -1.1(3) 1_555 1_555 1_555 1_555 yes
C(7) C(4) O(1) C(9) -73.4(7) 1_555 1_555 1_555 1_555 yes
C(7) C(4) C(5) C(13) -116.7(4) 1_555 1_555 1_555 1_555 yes
C(7) C(6) C(5) C(13) 115.7(4) 1_555 1_555 1_555 1_555 yes
C(8) C(6) C(5) C(13) -66.8(7) 1_555 1_555 1_555 1_555 yes
