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#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/50/53/1505336.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_1505336
loop_
_publ_author_name
'Wada, Azusa'
'Noguchi, Keiichi'
'Hirano, Masao'
'Tanaka, Ken'
_publ_section_title
;
 Enantioselective synthesis of C2 -symmetric spirobipyridine ligands
 through cationic Rh(I)/modified-BINAP- catalyzed double [2 + 2 + 2]
 cycloaddition.
;
_journal_issue                   7
_journal_name_full               'Organic letters'
_journal_page_first              1295
_journal_page_last               1298
_journal_paper_doi               10.1021/ol070129e
_journal_volume                  9
_journal_year                    2007
_chemical_absolute_configuration ad
_chemical_formula_moiety         'C31 H24 Cl2 N2 O2'
_chemical_formula_sum            'C31 H24 Cl2 N2 O2'
_chemical_formula_weight         527.42
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           5
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      5
_symmetry_space_group_name_Hall  'C 2y'
_symmetry_space_group_name_H-M   'C 1 2 1'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_date             2006-12-19
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 121.939(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   21.612(2)
_cell_length_b                   5.5038(6)
_cell_length_c                   11.8718(12)
_cell_measurement_reflns_used    10246
_cell_measurement_temperature    193
_cell_measurement_theta_max      68.2
_cell_measurement_theta_min      4.4
_cell_volume                     1198.3(2)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       PROCESS-AUTO
_computing_data_reduction        CrystalStructure
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    SIR2004
_diffrn_ambient_temperature      193
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'rotating anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0393
_diffrn_reflns_av_sigmaI/netI    0.0292
_diffrn_reflns_limit_h_max       26
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_number            10456
_diffrn_reflns_theta_full        68.24
_diffrn_reflns_theta_max         68.24
_diffrn_reflns_theta_min         4.39
_exptl_absorpt_coefficient_mu    2.711
_exptl_absorpt_correction_T_max  0.873
_exptl_absorpt_correction_T_min  0.596
_exptl_absorpt_correction_type   numerical
_exptl_absorpt_process_details
;
    Higashi, T. (1999). Program for Absorption Correction.
    Rigaku Corporation, Tokyo, Japan.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.462
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             548
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.156
_refine_diff_density_min         -0.226
_refine_diff_density_rms         0.045
_refine_ls_abs_structure_details
'Flack H D (1983), Acta Cryst. A39, 876-881 865 Friedel Pairs'
_refine_ls_abs_structure_Flack   0.001(15)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     178
_refine_ls_number_reflns         2096
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0321
_refine_ls_R_factor_gt           0.0306
_refine_ls_shift/su_max          0.004
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0480P)²+0.3839P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0787
_refine_ls_wR_factor_ref         0.0803
_reflns_number_gt                1993
_reflns_number_total             2096
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol070129esi20070119_113756.cif
_cod_data_source_block           global
_cod_original_cell_volume        1198.4(2)
_cod_database_code               1505336
loop_
_symmetry_equiv_pos_site_id
_symmetry_equiv_pos_as_xyz
1 +X,+Y,+Z
2 -X,+Y,-Z
3 1/2+X,1/2+Y,+Z
4 1/2-X,1/2+Y,-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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl1 Cl 0.24514(3) 1.56727(15) 0.20917(5) 0.0608(2) Uani 1 1 d . A .
O1 O 0.6740(4) 1.069(4) 0.5223(16) 0.062(3) Uani 0.65(5) 1 d P A 1
O2 O 0.6600(16) 0.984(6) 0.5470(11) 0.055(6) Uani 0.35(5) 1 d P A 2
N1 N 0.46542(7) 0.8573(3) 0.11640(13) 0.0268(3) Uani 1 1 d . A .
C1 C 0.5000 0.5550(5) 0.0000 0.0281(5) Uani 1 2 d S . .
C2 C 0.57132(11) 0.4031(4) 0.05919(18) 0.0396(5) Uani 1 1 d . . .
H2A H 0.5617 0.2325 0.0719 0.048 Uiso 1 1 calc R . .
H2B H 0.5891 0.4045 -0.0024 0.048 Uiso 1 1 calc R . .
C3 C 0.62832(10) 0.5126(4) 0.19129(19) 0.0433(5) Uani 1 1 d . . .
H3A H 0.6505 0.3863 0.2612 0.052 Uiso 1 1 calc R . .
H3B H 0.6673 0.5926 0.1848 0.052 Uiso 1 1 calc R . .
C4 C 0.58749(9) 0.6937(4) 0.22086(16) 0.0300(4) Uani 1 1 d . . .
C5 C 0.51516(9) 0.7152(3) 0.11660(15) 0.0250(3) Uani 1 1 d . . .
C6 C 0.60871(9) 0.8400(4) 0.33039(17) 0.0345(4) Uani 1 1 d . A .
C7 C 0.68032(11) 0.8591(6) 0.4592(2) 0.0571(7) Uani 1 1 d . . .
H7A H 0.6894 0.7127 0.5142 0.069 Uiso 1 1 calc R A 1
H7B H 0.7207 0.8780 0.4435 0.069 Uiso 1 1 calc R A 1
C8 C 0.59803(11) 1.1340(5) 0.46152(19) 0.0509(6) Uani 1 1 d . . .
H8A H 0.5913 1.3114 0.4463 0.061 Uiso 1 1 calc R A 1
H8B H 0.5795 1.0844 0.5186 0.061 Uiso 1 1 calc R A 1
C9 C 0.55888(10) 0.9977(4) 0.33107(16) 0.0324(4) Uani 1 1 d . A .
C10 C 0.48679(9) 1.0000(3) 0.22388(16) 0.0279(4) Uani 1 1 d . . .
C11 C 0.42820(10) 1.1481(4) 0.22078(16) 0.0308(4) Uani 1 1 d . A .
C12 C 0.44176(11) 1.3682(4) 0.28840(19) 0.0369(4) Uani 1 1 d . . .
H12 H 0.4901 1.4300 0.3379 0.044 Uiso 1 1 calc R A .
C13 C 0.38545(12) 1.4978(4) 0.28420(19) 0.0420(5) Uani 1 1 d . A .
H13 H 0.3950 1.6479 0.3300 0.050 Uiso 1 1 calc R . .
C14 C 0.31557(12) 1.4063(4) 0.21283(19) 0.0422(5) Uani 1 1 d . . .
C15 C 0.30033(11) 1.1915(5) 0.14373(19) 0.0417(5) Uani 1 1 d . A .
H15 H 0.2518 1.1317 0.0940 0.050 Uiso 1 1 calc R . .
C16 C 0.35639(9) 1.0637(4) 0.14739(16) 0.0351(4) Uani 1 1 d . . .
H16 H 0.3460 0.9160 0.0992 0.042 Uiso 1 1 calc R A .
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'
N N 0.0311 0.0180 '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'
Cl Cl 0.3639 0.7018 '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
C7 O1 C8 109.8(4) . .
C8 O2 C7 106.2(10) . .
C5 N1 C10 117.86(14) . .
C5 C1 C5 109.3(2) . 2_655
C5 C1 C2 113.99(9) . 2_655
C5 C1 C2 102.42(9) 2_655 2_655
C5 C1 C2 102.42(9) . .
C5 C1 C2 113.99(9) 2_655 .
C2 C1 C2 115.0(2) 2_655 .
C3 C2 C1 108.80(15) . .
C3 C2 H2A 109.9 . .
C1 C2 H2A 109.9 . .
C3 C2 H2B 109.9 . .
C1 C2 H2B 109.9 . .
H2A C2 H2B 108.3 . .
C4 C3 C2 104.55(15) . .
C4 C3 H3A 110.8 . .
C2 C3 H3A 110.8 . .
C4 C3 H3B 110.8 . .
C2 C3 H3B 110.8 . .
H3A C3 H3B 108.9 . .
C6 C4 C5 116.31(16) . .
C6 C4 C3 131.79(16) . .
C5 C4 C3 111.90(15) . .
N1 C5 C4 125.31(15) . .
N1 C5 C1 123.65(13) . .
C4 C5 C1 111.04(13) . .
C4 C6 C9 119.80(16) . .
C4 C6 C7 130.52(18) . .
C9 C6 C7 109.67(17) . .
O1 C7 C6 105.0(3) . .
O2 C7 C6 102.6(8) . .
O1 C7 H7A 110.7 . .
O2 C7 H7A 86.7 . .
C6 C7 H7A 110.7 . .
O1 C7 H7B 110.7 . .
O2 C7 H7B 134.1 . .
C6 C7 H7B 110.7 . .
H7A C7 H7B 108.8 . .
O2 C8 C9 104.2(5) . .
O1 C8 C9 105.1(3) . .
O2 C8 H8A 133.4 . .
O1 C8 H8A 110.7 . .
C9 C8 H8A 110.7 . .
O2 C8 H8B 85.5 . .
O1 C8 H8B 110.7 . .
C9 C8 H8B 110.7 . .
H8A C8 H8B 108.8 . .
C6 C9 C10 119.75(16) . .
C6 C9 C8 107.51(15) . .
C10 C9 C8 132.70(16) . .
N1 C10 C9 120.87(15) . .
N1 C10 C11 115.60(14) . .
C9 C10 C11 123.49(15) . .
C12 C11 C16 118.24(17) . .
C12 C11 C10 122.91(17) . .
C16 C11 C10 118.86(17) . .
C13 C12 C11 120.8(2) . .
C13 C12 H12 119.6 . .
C11 C12 H12 119.6 . .
C14 C13 C12 119.3(2) . .
C14 C13 H13 120.4 . .
C12 C13 H13 120.4 . .
C15 C14 C13 121.30(18) . .
C15 C14 Cl1 119.46(17) . .
C13 C14 Cl1 119.24(17) . .
C14 C15 C16 119.3(2) . .
C14 C15 H15 120.4 . .
C16 C15 H15 120.4 . .
C15 C16 C11 121.1(2) . .
C15 C16 H16 119.4 . .
C11 C16 H16 119.4 . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
Cl1 C14 1.7418(19) .
O1 C7 1.423(7) .
O1 C8 1.445(6) .
O2 C8 1.438(10) .
O2 C7 1.496(17) .
N1 C5 1.328(2) .
N1 C10 1.355(2) .
C1 C5 1.523(2) .
C1 C5 1.523(2) 2_655
C1 C2 1.557(2) 2_655
C1 C2 1.557(2) .
C2 C3 1.515(3) .
C2 H2A 0.9900 .
C2 H2B 0.9900 .
C3 C4 1.491(3) .
C3 H3A 0.9900 .
C3 H3B 0.9900 .
C4 C6 1.385(3) .
C4 C5 1.394(2) .
C6 C9 1.386(3) .
C6 C7 1.497(2) .
C7 H7A 0.9900 .
C7 H7B 0.9900 .
C8 C9 1.514(3) .
C8 H8A 0.9900 .
C8 H8B 0.9900 .
C9 C10 1.396(2) .
C10 C11 1.490(2) .
C11 C12 1.396(3) .
C11 C16 1.397(3) .
C12 C13 1.389(3) .
C12 H12 0.9500 .
C13 C14 1.378(3) .
C13 H13 0.9500 .
C14 C15 1.376(3) .
C15 C16 1.382(3) .
C15 H15 0.9500 .
C16 H16 0.9500 .
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
C5 C1 C2 C3 -11.4(2) .
C5 C1 C2 C3 106.49(17) 2_655
C2 C1 C2 C3 -135.64(17) 2_655
C1 C2 C3 C4 10.2(2) .
C2 C3 C4 C6 175.6(2) .
C2 C3 C4 C5 -4.8(2) .
C10 N1 C5 C4 2.5(2) .
C10 N1 C5 C1 -176.78(16) .
C6 C4 C5 N1 -2.3(3) .
C3 C4 C5 N1 178.04(17) .
C6 C4 C5 C1 177.06(16) .
C3 C4 C5 C1 -2.6(2) .
C5 C1 C5 N1 66.75(14) 2_655
C2 C1 C5 N1 -47.1(2) 2_655
C2 C1 C5 N1 -172.04(16) .
C5 C1 C5 C4 -112.60(14) 2_655
C2 C1 C5 C4 133.50(16) 2_655
C2 C1 C5 C4 8.61(19) .
C5 C4 C6 C9 -0.5(3) .
C3 C4 C6 C9 179.1(2) .
C5 C4 C6 C7 178.2(2) .
C3 C4 C6 C7 -2.2(4) .
C8 O1 C7 O2 -71.2(10) .
C8 O1 C7 C6 17(2) .
C8 O2 C7 O1 68.9(15) .
C8 O2 C7 C6 -29(3) .
C4 C6 C7 O1 169.4(12) .
C9 C6 C7 O1 -11.7(13) .
C4 C6 C7 O2 -162.2(17) .
C9 C6 C7 O2 16.6(17) .
C7 O2 C8 O1 -64.6(19) .
C7 O2 C8 C9 31(3) .
C7 O1 C8 O2 75.7(14) .
C7 O1 C8 C9 -16(2) .
C4 C6 C9 C10 2.9(3) .
C7 C6 C9 C10 -176.08(19) .
C4 C6 C9 C8 -179.13(19) .
C7 C6 C9 C8 1.9(2) .
O2 C8 C9 C6 -21(2) .
O1 C8 C9 C6 8.5(12) .
O2 C8 C9 C10 157(2) .
O1 C8 C9 C10 -173.9(12) .
C5 N1 C10 C9 0.1(2) .
C5 N1 C10 C11 -177.63(15) .
C6 C9 C10 N1 -2.8(3) .
C8 C9 C10 N1 179.9(2) .
C6 C9 C10 C11 174.82(18) .
C8 C9 C10 C11 -2.6(3) .
N1 C10 C11 C12 -152.81(16) .
C9 C10 C11 C12 29.5(3) .
N1 C10 C11 C16 27.4(2) .
C9 C10 C11 C16 -150.32(18) .
C16 C11 C12 C13 0.9(3) .
C10 C11 C12 C13 -178.96(17) .
C11 C12 C13 C14 0.4(3) .
C12 C13 C14 C15 -1.2(3) .
C12 C13 C14 Cl1 179.27(14) .
C13 C14 C15 C16 0.8(3) .
Cl1 C14 C15 C16 -179.69(15) .
C14 C15 C16 C11 0.5(3) .
C12 C11 C16 C15 -1.3(3) .
C10 C11 C16 C15 178.54(16) .
