#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/57/4025736.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_4025736
loop_
_publ_author_name
'Takumi Furuta'
'Junya Yamamoto'
'Yuki Kitamura'
'Ayano Hashimoto'
'Hyuma Masu'
'Isao Azumaya'
'Toshiyuki Kan'
'Takeo Kawabata'
_publ_section_title
;
 Synthesis of Axially Chiral Amino Acid and Amino Alcohols via
 Additive-Ligand-Free Pd-Catalyzed Domino Coupling Reaction and Subsequent
 Transformations of the Product Amidoaza[5]helicene
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              7010
_journal_page_last               7013
_journal_paper_doi               10.1021/jo101524t
_journal_volume                  75
_journal_year                    2010
_chemical_formula_sum            'C26 H23 N O4'
_chemical_formula_weight         413.45
_chemical_name_systematic
; (dl)-2'-(tert-Butoxycarbonylamino)-1,1'-binaphthyl-2-carboxylic acid
 ? 
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                103.724(2)
_cell_angle_beta                 97.607(2)
_cell_angle_gamma                112.5900(10)
_cell_formula_units_Z            2
_cell_length_a                   9.5527(14)
_cell_length_b                   10.1375(15)
_cell_length_c                   14.453(2)
_cell_measurement_reflns_used    1906
_cell_measurement_temperature    150
_cell_measurement_theta_max      25.62
_cell_measurement_theta_min      2.29
_cell_volume                     1215.8(3)
_computing_cell_refinement       'APEX2 (Bruker AXS, 2006)'
_computing_data_collection       'APEX2 (Bruker AXS, 2006)'
_computing_data_reduction        'SAINT (Bruker AXS, 2004)'
_computing_molecular_graphics    'XSHEL (Bruker AXS,2002)'
_computing_publication_material  'XCIF (Bruker AXS, 2001)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      150
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 0.955
_diffrn_measured_fraction_theta_max 0.851
_diffrn_measurement_device_type  'Bruker APEXII CCD area detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0124
_diffrn_reflns_av_sigmaI/netI    0.0326
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            5763
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         26.94
_diffrn_reflns_theta_min         2.29
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  0.9738
_exptl_absorpt_correction_T_min  0.9665
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
;
SADABS Sheldrick 1996
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.129
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             436
_exptl_crystal_size_max          0.45
_exptl_crystal_size_mid          0.40
_exptl_crystal_size_min          0.35
_platon_squeeze_details
;
;
_refine_diff_density_max         0.216
_refine_diff_density_min         -0.211
_refine_diff_density_rms         0.042
_refine_ls_extinction_coef       0.021(3)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     284
_refine_ls_number_reflns         4476
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.091
_refine_ls_R_factor_all          0.0638
_refine_ls_R_factor_gt           0.0462
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0773P)²+0.0055P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1295
_refine_ls_wR_factor_ref         0.1402
_reflns_number_gt                3210
_reflns_number_total             4476
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo101524t_si_005.cif
_cod_data_source_block           a0902201mas
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Triclinic' changed to 'triclinic'
according to the built-in table from CIF Core dictionary named
'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1646 2011-03-28 12:23:43Z adriana 
;
_cod_original_cell_volume        1215.7(3)
_cod_original_sg_symbol_H-M      'P -1 '
_cod_database_code               4025736
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -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
C1 C -0.08414(19) 0.71386(19) 0.19312(13) 0.0343(4) Uani 1 1 d . . .
C2 C 0.17581(17) 0.85342(17) 0.16547(11) 0.0262(4) Uani 1 1 d . . .
C3 C 0.17704(19) 0.73036(18) 0.09637(12) 0.0317(4) Uani 1 1 d . . .
H3 H 0.0862 0.6371 0.0719 0.038 Uiso 1 1 calc R . .
C4 C 0.3082(2) 0.74488(19) 0.06454(13) 0.0359(4) Uani 1 1 d . . .
H4A H 0.3073 0.6612 0.0174 0.043 Uiso 1 1 calc R . .
C5 C 0.44508(19) 0.88087(18) 0.09967(12) 0.0332(4) Uani 1 1 d . . .
C6 C 0.5830(2) 0.8968(2) 0.06847(14) 0.0451(5) Uani 1 1 d . . .
H6 H 0.5851 0.8137 0.0225 0.054 Uiso 1 1 calc R . .
C7 C 0.7132(2) 1.0308(2) 0.10388(16) 0.0548(6) Uani 1 1 d . . .
H7 H 0.8062 1.0399 0.0835 0.066 Uiso 1 1 calc R . .
C8 C 0.7108(2) 1.1538(2) 0.16945(16) 0.0561(6) Uani 1 1 d . . .
H8 H 0.8019 1.2470 0.1927 0.067 Uiso 1 1 calc R . .
C9 C 0.5796(2) 1.1432(2) 0.20120(14) 0.0444(5) Uani 1 1 d . . .
H9 H 0.5800 1.2288 0.2461 0.053 Uiso 1 1 calc R . .
C10 C 0.44268(18) 1.00491(18) 0.16738(12) 0.0301(4) Uani 1 1 d . . .
C11 C 0.30534(18) 0.98960(17) 0.20024(11) 0.0262(4) Uani 1 1 d . . .
C12 C 0.30080(17) 1.12488(17) 0.26643(12) 0.0273(4) Uani 1 1 d . . .
C13 C 0.35988(19) 1.17633(18) 0.36692(12) 0.0311(4) Uani 1 1 d . . .
C14 C 0.3598(2) 1.31056(19) 0.42448(13) 0.0368(4) Uani 1 1 d . . .
H14 H 0.4043 1.3468 0.4934 0.044 Uiso 1 1 calc R . .
C15 C 0.2971(2) 1.38749(19) 0.38248(13) 0.0380(4) Uani 1 1 d . . .
H15 H 0.2963 1.4761 0.4226 0.046 Uiso 1 1 calc R . .
C16 C 0.23308(18) 1.33911(17) 0.28077(13) 0.0319(4) Uani 1 1 d . . .
C17 C 0.1652(2) 1.41598(19) 0.23480(15) 0.0408(5) Uani 1 1 d . . .
H17 H 0.1607 1.5034 0.2737 0.049 Uiso 1 1 calc R . .
C18 C 0.1063(2) 1.3673(2) 0.13602(15) 0.0428(5) Uani 1 1 d . . .
H18 H 0.0584 1.4191 0.1067 0.051 Uiso 1 1 calc R . .
C19 C 0.11554(19) 1.2417(2) 0.07739(14) 0.0393(4) Uani 1 1 d . . .
H19 H 0.0772 1.2105 0.0080 0.047 Uiso 1 1 calc R . .
C20 C 0.17909(18) 1.16344(18) 0.11868(12) 0.0317(4) Uani 1 1 d . . .
H20 H 0.1839 1.0776 0.0777 0.038 Uiso 1 1 calc R . .
C21 C 0.23778(17) 1.20775(17) 0.22112(12) 0.0276(4) Uani 1 1 d . . .
C22 C 0.4252(2) 1.09812(19) 0.42154(12) 0.0324(4) Uani 1 1 d . . .
C23 C -0.33039(19) 0.6387(2) 0.24393(14) 0.0403(5) Uani 1 1 d . . .
C24 C -0.4075(2) 0.7326(2) 0.29021(15) 0.0474(5) Uani 1 1 d . . .
H24A H -0.3401 0.8016 0.3548 0.071 Uiso 1 1 calc R . .
H24B H -0.5086 0.6666 0.2980 0.071 Uiso 1 1 calc R . .
H24C H -0.4240 0.7906 0.2480 0.071 Uiso 1 1 calc R . .
C25 C -0.4305(2) 0.5327(2) 0.14387(15) 0.0590(6) Uani 1 1 d . . .
H25A H -0.4391 0.5908 0.0998 0.089 Uiso 1 1 calc R . .
H25B H -0.5351 0.4712 0.1495 0.089 Uiso 1 1 calc R . .
H25C H -0.3826 0.4671 0.1171 0.089 Uiso 1 1 calc R . .
C26 C -0.2875(3) 0.5593(2) 0.31158(17) 0.0571(6) Uani 1 1 d . . .
H26A H -0.2328 0.5032 0.2810 0.086 Uiso 1 1 calc R . .
H26B H -0.3828 0.4894 0.3231 0.086 Uiso 1 1 calc R . .
H26C H -0.2189 0.6338 0.3744 0.086 Uiso 1 1 calc R . .
N1 N 0.03993(15) 0.84120(15) 0.19745(10) 0.0332(4) Uani 1 1 d . . .
H1 H 0.0347 0.9264 0.2234 0.040 Uiso 1 1 calc R . .
O1 O -0.09981(16) 0.58780(14) 0.15767(12) 0.0600(5) Uani 1 1 d . . .
O2 O -0.18526(13) 0.75324(12) 0.23473(9) 0.0368(3) Uani 1 1 d . . .
O3 O 0.51826(16) 1.17013(15) 0.50357(9) 0.0510(4) Uani 1 1 d . . .
O4 O 0.37945(16) 0.95687(13) 0.38260(9) 0.0511(4) Uani 1 1 d . . .
H4 H 0.4237 0.9248 0.4200 0.077 Uiso 1 1 calc R . .
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 '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 0.0061 0.0033 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 '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
O1 C1 O2 126.17(15) . . ?
O1 C1 N1 125.50(16) . . ?
O2 C1 N1 108.34(14) . . ?
C11 C2 N1 118.60(14) . . ?
C11 C2 C3 120.67(15) . . ?
N1 C2 C3 120.68(14) . . ?
C4 C3 C2 120.00(15) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C4 C5 121.53(16) . . ?
C3 C4 H4A 119.2 . . ?
C5 C4 H4A 119.2 . . ?
C4 C5 C10 118.39(15) . . ?
C4 C5 C6 122.14(16) . . ?
C10 C5 C6 119.47(16) . . ?
C7 C6 C5 120.39(18) . . ?
C7 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
C6 C7 C8 120.37(18) . . ?
C6 C7 H7 119.8 . . ?
C8 C7 H7 119.8 . . ?
C9 C8 C7 121.05(18) . . ?
C9 C8 H8 119.5 . . ?
C7 C8 H8 119.5 . . ?
C8 C9 C10 120.22(18) . . ?
C8 C9 H9 119.9 . . ?
C10 C9 H9 119.9 . . ?
C5 C10 C9 118.48(16) . . ?
C5 C10 C11 119.94(15) . . ?
C9 C10 C11 121.57(16) . . ?
C2 C11 C10 119.43(15) . . ?
C2 C11 C12 121.16(14) . . ?
C10 C11 C12 119.26(13) . . ?
C13 C12 C21 119.12(15) . . ?
C13 C12 C11 123.56(15) . . ?
C21 C12 C11 117.25(14) . . ?
C12 C13 C14 120.44(16) . . ?
C12 C13 C22 123.64(15) . . ?
C14 C13 C22 115.92(15) . . ?
C15 C14 C13 120.75(16) . . ?
C15 C14 H14 119.6 . . ?
C13 C14 H14 119.6 . . ?
C14 C15 C16 121.25(17) . . ?
C14 C15 H15 119.4 . . ?
C16 C15 H15 119.4 . . ?
C15 C16 C17 122.64(17) . . ?
C15 C16 C21 118.83(16) . . ?
C17 C16 C21 118.53(16) . . ?
C18 C17 C16 121.15(18) . . ?
C18 C17 H17 119.4 . . ?
C16 C17 H17 119.4 . . ?
C17 C18 C19 120.27(17) . . ?
C17 C18 H18 119.9 . . ?
C19 C18 H18 119.9 . . ?
C20 C19 C18 120.56(17) . . ?
C20 C19 H19 119.7 . . ?
C18 C19 H19 119.7 . . ?
C19 C20 C21 120.96(16) . . ?
C19 C20 H20 119.5 . . ?
C21 C20 H20 119.5 . . ?
C20 C21 C16 118.47(15) . . ?
C20 C21 C12 122.00(15) . . ?
C16 C21 C12 119.53(15) . . ?
O3 C22 O4 122.62(16) . . ?
O3 C22 C13 119.47(15) . . ?
O4 C22 C13 117.89(14) . . ?
O2 C23 C24 102.32(14) . . ?
O2 C23 C25 110.28(15) . . ?
C24 C23 C25 110.64(16) . . ?
O2 C23 C26 108.75(14) . . ?
C24 C23 C26 111.26(16) . . ?
C25 C23 C26 113.05(17) . . ?
C23 C24 H24A 109.5 . . ?
C23 C24 H24B 109.5 . . ?
H24A C24 H24B 109.5 . . ?
C23 C24 H24C 109.5 . . ?
H24A C24 H24C 109.5 . . ?
H24B C24 H24C 109.5 . . ?
C23 C25 H25A 109.5 . . ?
C23 C25 H25B 109.5 . . ?
H25A C25 H25B 109.5 . . ?
C23 C25 H25C 109.5 . . ?
H25A C25 H25C 109.5 . . ?
H25B C25 H25C 109.5 . . ?
C23 C26 H26A 109.5 . . ?
C23 C26 H26B 109.5 . . ?
H26A C26 H26B 109.5 . . ?
C23 C26 H26C 109.5 . . ?
H26A C26 H26C 109.5 . . ?
H26B C26 H26C 109.5 . . ?
C1 N1 C2 127.86(14) . . ?
C1 N1 H1 116.1 . . ?
C2 N1 H1 116.1 . . ?
C1 O2 C23 121.06(13) . . ?
C22 O4 H4 109.5 . . ?
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
C1 O1 1.200(2) . ?
C1 O2 1.338(2) . ?
C1 N1 1.357(2) . ?
C2 C11 1.372(2) . ?
C2 N1 1.406(2) . ?
C2 C3 1.406(2) . ?
C3 C4 1.358(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.406(2) . ?
C4 H4A 0.9500 . ?
C5 C10 1.408(2) . ?
C5 C6 1.412(2) . ?
C6 C7 1.363(3) . ?
C6 H6 0.9500 . ?
C7 C8 1.386(3) . ?
C7 H7 0.9500 . ?
C8 C9 1.366(3) . ?
C8 H8 0.9500 . ?
C9 C10 1.418(2) . ?
C9 H9 0.9500 . ?
C10 C11 1.419(2) . ?
C11 C12 1.494(2) . ?
C12 C13 1.377(2) . ?
C12 C21 1.429(2) . ?
C13 C14 1.417(2) . ?
C13 C22 1.479(2) . ?
C14 C15 1.350(2) . ?
C14 H14 0.9500 . ?
C15 C16 1.402(2) . ?
C15 H15 0.9500 . ?
C16 C17 1.410(2) . ?
C16 C21 1.425(2) . ?
C17 C18 1.356(3) . ?
C17 H17 0.9500 . ?
C18 C19 1.393(3) . ?
C18 H18 0.9500 . ?
C19 C20 1.361(2) . ?
C19 H19 0.9500 . ?
C20 C21 1.407(2) . ?
C20 H20 0.9500 . ?
C22 O3 1.241(2) . ?
C22 O4 1.277(2) . ?
C23 O2 1.4742(19) . ?
C23 C24 1.504(3) . ?
C23 C25 1.506(3) . ?
C23 C26 1.514(3) . ?
C24 H24A 0.9800 . ?
C24 H24B 0.9800 . ?
C24 H24C 0.9800 . ?
C25 H25A 0.9800 . ?
C25 H25B 0.9800 . ?
C25 H25C 0.9800 . ?
C26 H26A 0.9800 . ?
C26 H26B 0.9800 . ?
C26 H26C 0.9800 . ?
N1 H1 0.8800 . ?
O4 H4 0.8400 . ?
loop_
_platon_squeeze_void_nr
_platon_squeeze_void_average_x
_platon_squeeze_void_average_y
_platon_squeeze_void_average_z
_platon_squeeze_void_volume
_platon_squeeze_void_count_electrons
1 0.000 0.044 0.500 231.4 40.9
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30659289
