#------------------------------------------------------------------------------
#$Date: 2016-02-16 22:30:59 +0200 (Tue, 16 Feb 2016) $
#$Revision: 176467 $
#$URL: svn://www.crystallography.net/cod/cif/4/10/54/4105404.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_4105404
loop_
_publ_author_name
'Kazuyuki Matsumura'
'Tadashi Mori'
'Yoshihisa Inoue'
_publ_contact_author_email       tmori@chem.eng.osaka-u.ac.jp
_publ_contact_author_fax         +81-6-6879-7923
_publ_contact_author_name        'Tadashi Mori'
_publ_contact_author_phone       +81-6-6879-7921
_publ_section_title
;
 Wavelength Control of Diastereodifferentiating Paternó-Büchi Reaction
 of Chiral Cyanobenzoates with Diphenylethene through Direct versus
 Charge-Transfer Excitation
;
_journal_name_full               'Journal of the American Chemical Society'
_journal_page_first              17076
_journal_page_last               17077
_journal_paper_doi               10.1021/ja907156j
_journal_volume                  131
_journal_year                    2009
_chemical_formula_moiety         'C26 H25 N O2 '
_chemical_formula_sum            'C26 H25 N O2'
_chemical_formula_weight         383.49
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_symmetry_Int_Tables_number      19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_audit_creation_date             2006-12-13
_audit_creation_method           'by CrystalStructure v3.5.1'
_cell_angle_alpha                90.000(4)
_cell_angle_beta                 90.000(4)
_cell_angle_gamma                90.000(3)
_cell_formula_units_Z            4
_cell_length_a                   9.5836(8)
_cell_length_b                   12.2635(8)
_cell_length_c                   18.164(2)
_cell_measurement_reflns_used    13304
_cell_measurement_temperature    296.1
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.7
_cell_volume                     2134.8(3)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       PROCESS-AUTO
_computing_data_reduction        CrystalStructure
_computing_publication_material  'CrystalStructure Ver. 3.5.1'
_computing_structure_refinement  CRYSTALS
_computing_structure_solution    SIR92
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.9954
_diffrn_measured_fraction_theta_max 0.9954
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       ω
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.7107
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            5604
_diffrn_reflns_theta_full        27.52
_diffrn_reflns_theta_max         27.52
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.193
_exptl_crystal_description       prism
_exptl_crystal_F_000             816.00
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.37
_refine_diff_density_min         -0.26
_refine_ls_abs_structure_details
'Flack, H. D. (1983), Acta Cryst. A39, 876-881.  0 Friedel Pairs'
_refine_ls_abs_structure_Flack   3(4)
_refine_ls_extinction_coef       208(63)
_refine_ls_extinction_method
'Larson (1970) Crystallographic Computing eq. 22'
_refine_ls_goodness_of_fit_ref   1.386
_refine_ls_hydrogen_treatment    mixed
_refine_ls_number_parameters     337
_refine_ls_number_reflns         2287
_refine_ls_R_factor_gt           0.0850
_refine_ls_shift/su_max          0.0490
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details
'w = 1/[0.0010Fo² + 3.0000σ(Fo²) + 0.5000]'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0820
_reflns_number_gt                2271
_reflns_number_total             2802
_reflns_threshold_expression     F²>2.0σ(F²)
_cod_data_source_file            ja907156j_si_002.cif
_cod_data_source_block           '_km-oxetane'
_cod_original_sg_symbol_H-M      'P 21 21 21 '
_cod_original_formula_sum        'C26 H25 N O2 '
_cod_database_code               4105404
loop_
_symmetry_equiv_pos_as_xyz
x,y,z
x+1/2,-y+1/2,-z
-x,y+1/2,-z+1/2
-x+1/2,-y,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
O(1) O 1.0451(4) 0.1778(2) 0.3459(2) 0.058(1) Uani 1.00 1 d
O(2) O 1.1790(3) 0.0324(3) 0.3908(2) 0.0526(9) Uani 1.00 1 d
N(1) N 0.4785(5) -0.2310(5) 0.4310(3) 0.089(2) Uani 1.00 1 d
C(1) C 0.9365(5) -0.0007(3) 0.3624(2) 0.045(1) Uani 1.00 1 d
C(2) C 0.9459(6) -0.1058(4) 0.3890(3) 0.052(1) Uani 1.00 1 d
C(3) C 0.8267(5) -0.1641(4) 0.4056(3) 0.056(1) Uani 1.00 1 d
C(4) C 0.6972(5) -0.1184(4) 0.3957(3) 0.054(1) Uani 1.00 1 d
C(5) C 0.6854(6) -0.0135(4) 0.3689(3) 0.063(2) Uani 1.00 1 d
C(6) C 0.8044(6) 0.0444(4) 0.3528(3) 0.060(1) Uani 1.00 1 d
C(7) C 0.5733(6) -0.1807(5) 0.4155(3) 0.066(2) Uani 1.00 1 d
C(8) C 1.0679(5) 0.0620(3) 0.3450(3) 0.048(1) Uani 1.00 1 d
C(9) C 1.1694(7) 0.0577(5) 0.4685(3) 0.074(2) Uani 1.00 1 d
C(10) C 1.2360(9) -0.0334(5) 0.5090(3) 0.094(2) Uani 1.00 1 d
C(11) C 1.255(2) 0.1635(7) 0.4798(6) 0.222(6) Uani 1.00 1 d
C(12) C 1.278(3) 0.213(1) 0.520(1) 0.38(1) Uani 1.00 1 d
C(13) C 1.1273(4) 0.0710(3) 0.2643(2) 0.043(1) Uani 1.00 1 d
C(14) C 1.1440(6) 0.1907(4) 0.2864(3) 0.057(1) Uani 1.00 1 d
C(15) C 1.2619(4) 0.0120(4) 0.2462(3) 0.050(1) Uani 1.00 1 d
C(16) C 1.3626(6) 0.0650(6) 0.2048(4) 0.070(2) Uani 1.00 1 d
C(17) C 1.4825(6) 0.0147(8) 0.1837(4) 0.093(3) Uani 1.00 1 d
C(18) C 1.5049(7) -0.0904(8) 0.2019(5) 0.098(3) Uani 1.00 1 d
C(19) C 1.4081(7) -0.1466(6) 0.2427(4) 0.085(2) Uani 1.00 1 d
C(20) C 1.2868(6) -0.0950(5) 0.2654(3) 0.063(2) Uani 1.00 1 d
C(21) C 1.0166(4) 0.0533(3) 0.2046(3) 0.043(1) Uani 1.00 1 d
C(22) C 0.9263(6) 0.1345(4) 0.1830(3) 0.062(2) Uani 1.00 1 d
C(23) C 0.8317(6) 0.1186(5) 0.1265(4) 0.072(2) Uani 1.00 1 d
C(24) C 0.8216(5) 0.0205(5) 0.0917(3) 0.064(2) Uani 1.00 1 d
C(25) C 0.9075(5) -0.0624(5) 0.1137(3) 0.061(1) Uani 1.00 1 d
C(26) C 1.0037(5) -0.0461(4) 0.1691(3) 0.054(1) Uani 1.00 1 d
H(1) H 1.039(5) -0.134(3) 0.397(2) 0.04(1) Uiso 1.00 1 c
H(2) H 0.827(5) -0.244(4) 0.429(3) 0.07(1) Uiso 1.00 1 c
H(3) H 0.597(6) 0.020(5) 0.365(3) 0.08(2) Uiso 1.00 1 c
H(4) H 0.795(6) 0.116(5) 0.344(3) 0.08(2) Uiso 1.00 1 c
H(5) H 1.0781(7) 0.0739(5) 0.4856(3) 0.089(2) Uiso 1.00 1 c
H(6) H 1.3263(9) -0.0436(5) 0.4885(3) 0.113(3) Uiso 1.00 1 c
H(7) H 1.1828(9) -0.0982(5) 0.5029(3) 0.113(3) Uiso 1.00 1 c
H(8) H 1.2442(9) -0.0170(5) 0.5600(3) 0.113(3) Uiso 1.00 1 c
H(9) H 1.348(2) 0.1392(7) 0.4712(6) 0.27(1) Uiso 1.00 1 c
H(10) H 1.227(2) 0.2101(7) 0.4408(6) 0.27(1) Uiso 1.00 1 c
H(14) H 1.241(7) 0.207(5) 0.309(4) 0.10(2) Uiso 1.00 1 c
H(15) H 1.106(5) 0.247(4) 0.254(2) 0.05(1) Uiso 1.00 1 c
H(16) H 1.357(7) 0.132(5) 0.200(4) 0.09(2) Uiso 1.00 1 c
H(17) H 1.549(6) 0.052(5) 0.153(3) 0.08(2) Uiso 1.00 1 c
H(18) H 1.581(7) -0.126(5) 0.187(3) 0.10(2) Uiso 1.00 1 c
H(19) H 1.408(7) -0.228(5) 0.259(3) 0.09(2) Uiso 1.00 1 c
H(20) H 1.228(5) -0.129(4) 0.289(3) 0.06(2) Uiso 1.00 1 c
H(21) H 0.927(6) 0.198(5) 0.213(3) 0.09(2) Uiso 1.00 1 c
H(22) H 0.779(6) 0.167(5) 0.119(3) 0.08(2) Uiso 1.00 1 c
H(24) H 0.898(6) -0.139(5) 0.086(3) 0.09(2) Uiso 1.00 1 c
H(25) H 1.062(5) -0.107(4) 0.182(3) 0.06(1) Uiso 1.00 1 c
H(23) H 0.748(6) -0.008(5) 0.052(3) 0.08(2) Uiso 1.00 1 c
H(11) H 1.319(3) 0.173(1) 0.559(1) 0.46(2) Uiso 1.00 1 c
H(12) H 1.342(3) 0.267(1) 0.503(1) 0.46(2) Uiso 1.00 1 c
H(13) H 1.195(3) 0.247(1) 0.537(1) 0.46(2) Uiso 1.00 1 c
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.003 0.002
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
H H 0.000 0.000
;
International Tables for Crystallography
(1992, Vol. C, Table 6.1.1.4)
;
O O 0.011 0.006
;
International Tables for Crystallography
(1992, Vol. C, Tables 4.2.6.8 and 6.1.1.4)
;
N N 0.006 0.003
;
International Tables for Crystallography
(1992, 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
C(8) O(1) C(14) 90.0(3) yes
C(8) O(2) C(9) 118.4(4) yes
C(2) C(1) C(6) 118.3(4) yes
C(2) C(1) C(8) 119.7(4) yes
C(6) C(1) C(8) 122.0(4) yes
C(3) C(2) H(1) 123(2) no
C(3) C(2) C(1) 120.4(5) yes
H(1) C(2) C(1) 116(2) no
C(4) C(3) H(2) 115(2) no
C(4) C(3) C(2) 120.5(5) yes
H(2) C(3) C(2) 123(2) no
C(5) C(4) C(7) 120.6(5) yes
C(5) C(4) C(3) 120.0(5) yes
C(7) C(4) C(3) 119.3(5) yes
C(6) C(5) H(3) 120(3) no
C(6) C(5) C(4) 119.2(5) yes
H(3) C(5) C(4) 120(3) no
H(4) C(6) C(1) 119(3) no
H(4) C(6) C(5) 117(3) no
C(1) C(6) C(5) 121.5(5) yes
N(1) C(7) C(4) 178.7(6) yes
C(13) C(8) O(1) 89.9(3) yes
C(13) C(8) O(2) 107.3(3) yes
C(13) C(8) C(1) 122.1(4) yes
O(1) C(8) O(2) 111.4(3) yes
O(1) C(8) C(1) 112.0(4) yes
O(2) C(8) C(1) 112.2(4) yes
C(10) C(9) C(11) 109.7(7) yes
C(10) C(9) H(5) 113.1(7) no
C(10) C(9) O(2) 107.2(5) yes
C(11) C(9) H(5) 105.6(8) no
C(11) C(9) O(2) 105.9(6) yes
H(5) C(9) O(2) 115.0(6) no
H(6) C(10) H(7) 109.5(9) no
H(6) C(10) H(8) 109(1) no
H(6) C(10) C(9) 107.2(7) no
H(7) C(10) H(8) 109.5(8) no
H(7) C(10) C(9) 110.0(8) no
H(8) C(10) C(9) 111.0(7) no
C(12) C(11) H(9) 96(2) no
C(12) C(11) H(10) 104(1) no
C(12) C(11) C(9) 137(1) yes
H(9) C(11) H(10) 109(1) no
H(9) C(11) C(9) 102(1) no
H(10) C(11) C(9) 104(1) no
H(11) C(12) H(12) 109(3) no
H(11) C(12) H(13) 109(3) no
H(11) C(12) C(11) 109(1) no
H(12) C(12) H(13) 109(2) no
H(12) C(12) C(11) 109(2) no
H(13) C(12) C(11) 109(2) no
C(14) C(13) C(15) 115.2(4) yes
C(14) C(13) C(21) 113.2(4) yes
C(15) C(13) C(21) 111.6(4) yes
C(15) C(13) C(8) 118.4(4) yes
C(21) C(13) C(8) 113.5(3) yes
C(8) C(13) C(14) 82.0(3) yes
H(14) C(14) H(15) 116(4) no
H(14) C(14) O(1) 107(3) no
H(14) C(14) C(13) 112(3) no
H(15) C(14) O(1) 106(2) no
H(15) C(14) C(13) 118(2) no
C(13) C(14) O(1) 91.3(3) yes
C(16) C(15) C(20) 117.6(5) yes
C(16) C(15) C(13) 119.1(5) yes
C(20) C(15) C(13) 123.2(4) yes
C(17) C(16) H(16) 118(4) no
C(17) C(16) C(15) 122.0(7) yes
H(16) C(16) C(15) 118(4) no
C(18) C(17) H(17) 119(3) no
C(18) C(17) C(16) 119.9(7) yes
H(17) C(17) C(16) 120(3) no
C(19) C(18) H(18) 117(4) no
C(19) C(18) C(17) 120.4(7) yes
H(18) C(18) C(17) 121(4) no
C(20) C(19) H(19) 110(3) no
C(20) C(19) C(18) 119.8(7) yes
H(19) C(19) C(18) 129(3) no
H(20) C(20) C(15) 119(3) no
H(20) C(20) C(19) 119(3) no
C(15) C(20) C(19) 120.3(5) yes
C(22) C(21) C(26) 116.6(4) yes
C(22) C(21) C(13) 122.3(4) yes
C(26) C(21) C(13) 121.0(4) yes
C(23) C(22) H(21) 122(3) no
C(23) C(22) C(21) 121.4(5) yes
H(21) C(22) C(21) 115(3) no
C(24) C(23) H(22) 122(4) no
C(24) C(23) C(22) 121.0(6) yes
H(22) C(23) C(22) 116(4) no
C(25) C(24) H(23) 110(3) no
C(25) C(24) C(23) 118.6(5) yes
H(23) C(24) C(23) 130(3) no
C(26) C(25) H(24) 121(3) no
C(26) C(25) C(24) 120.5(5) yes
H(24) C(25) C(24) 118(3) no
H(25) C(26) C(21) 120(3) no
H(25) C(26) C(25) 117(2) no
C(21) C(26) C(25) 121.8(5) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
O(1) C(8) 1.437(5) yes
O(1) C(14) 1.446(6) yes
O(2) C(8) 1.400(6) yes
O(2) C(9) 1.447(6) yes
N(1) C(7) 1.134(8) yes
C(1) C(2) 1.380(6) yes
C(1) C(6) 1.393(7) yes
C(1) C(8) 1.509(6) yes
C(2) C(3) 1.381(7) yes
C(2) H(1) 0.97(5) no
C(3) C(4) 1.374(7) yes
C(3) H(2) 1.07(5) no
C(4) C(5) 1.381(7) yes
C(4) C(7) 1.457(7) yes
C(5) C(6) 1.375(8) yes
C(5) H(3) 0.95(6) no
C(6) H(4) 0.90(6) no
C(8) C(13) 1.576(6) yes
C(9) C(10) 1.482(9) yes
C(9) C(11) 1.55(1) yes
C(9) H(5) 0.950(9) no
C(10) H(6) 0.95(1) no
C(10) H(7) 0.95(1) no
C(10) H(8) 0.950(9) no
C(11) C(12) 0.98(2) yes
C(11) H(9) 0.95(3) no
C(11) H(10) 0.95(2) no
C(12) H(11) 0.95(3) no
C(12) H(12) 0.95(3) no
C(12) H(13) 0.95(3) no
C(13) C(14) 1.531(6) yes
C(13) C(15) 1.515(6) yes
C(13) C(21) 1.533(6) yes
C(14) H(14) 1.04(7) no
C(14) H(15) 0.98(4) no
C(15) C(16) 1.386(8) yes
C(15) C(20) 1.378(7) yes
C(16) C(17) 1.359(9) yes
C(16) H(16) 0.83(7) no
C(17) C(18) 1.35(1) yes
C(17) H(17) 0.96(6) no
C(18) C(19) 1.37(1) yes
C(18) H(18) 0.89(7) no
C(19) C(20) 1.386(9) yes
C(19) H(19) 1.04(6) no
C(20) H(20) 0.83(5) no
C(21) C(22) 1.377(7) yes
C(21) C(26) 1.385(7) yes
C(22) C(23) 1.383(8) yes
C(22) H(21) 0.95(6) no
C(23) C(24) 1.362(9) yes
C(23) H(22) 0.79(6) no
C(24) C(25) 1.368(8) yes
C(24) H(23) 1.06(6) no
C(25) C(26) 1.379(7) yes
C(25) H(24) 1.07(6) no
C(26) H(25) 0.96(5) no
