#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/57/4025738.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_4025738
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            'C33 H23 N'
_chemical_formula_weight         433.52
_chemical_name_systematic
; (S)-4,4-Diphenyl-3,4-dihydrodibenzo[a,k]phenanthridine
 ? 
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 110.6100(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.2718(10)
_cell_length_b                   9.1068(9)
_cell_length_c                   12.8312(13)
_cell_measurement_reflns_used    1720
_cell_measurement_temperature    100
_cell_measurement_theta_max      26.52
_cell_measurement_theta_min      2.81
_cell_volume                     1123.45(19)
_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      100
_diffrn_detector_area_resol_mean 8.333
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.903
_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  0.0229
_diffrn_reflns_av_sigmaI/netI    0.0396
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_number            5605
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         27.29
_diffrn_reflns_theta_min         1.70
_exptl_absorpt_coefficient_mu    0.074
_exptl_absorpt_correction_T_max  0.9985
_exptl_absorpt_correction_T_min  0.9818
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details
;
SADABS Sheldrick 1996
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.282
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             456
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.02
_refine_diff_density_max         0.429
_refine_diff_density_min         -0.328
_refine_diff_density_rms         0.041
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -6(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     307
_refine_ls_number_reflns         3348
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0464
_refine_ls_R_factor_gt           0.0382
_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)+(0.0475P)²+0.1648P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0873
_refine_ls_wR_factor_ref         0.0923
_reflns_number_gt                2929
_reflns_number_total             3348
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo101524t_si_007.cif
_cod_data_source_block           a0907091mas
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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_sg_symbol_H-M      'P 1 21 1 '
_cod_database_code               4025738
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, 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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.96389(18) 0.6424(2) 0.78833(14) 0.0179(4) Uani 1 1 d . . .
H1 H 1.0282 0.7072 0.8226 0.021 Uiso 1 1 calc R . .
C2 C 0.9531(2) 0.4644(3) 0.65020(17) 0.0161(5) Uani 1 1 d . . .
C9 C 0.8868(2) 0.4543(3) 0.41930(18) 0.0177(5) Uani 1 1 d . . .
C4 C 0.8000(2) 0.5348(3) 0.46492(17) 0.0161(5) Uani 1 1 d . . .
C16 C 0.3698(2) 0.5213(3) 0.49068(19) 0.0226(5) Uani 1 1 d . . .
H16 H 0.3141 0.4552 0.4358 0.027 Uiso 1 1 calc R . .
C8 C 0.8573(2) 0.4564(3) 0.30237(18) 0.0208(5) Uani 1 1 d . . .
H8 H 0.9137 0.4012 0.2717 0.025 Uiso 1 1 calc R . .
C1 C 0.9947(2) 0.4851(3) 0.77650(17) 0.0168(5) Uani 1 1 d . . .
C20 C 0.6184(2) 0.7941(3) 0.74940(18) 0.0198(5) Uani 1 1 d . . .
H20 H 0.5765 0.8656 0.7814 0.024 Uiso 1 1 calc R . .
C15 C 0.5120(2) 0.5173(3) 0.52105(17) 0.0193(5) Uani 1 1 d . . .
H15 H 0.5530 0.4488 0.4859 0.023 Uiso 1 1 calc R . .
C13 C 0.7481(2) 0.6091(3) 0.63953(17) 0.0158(5) Uani 1 1 d . . .
C27 C 1.2435(2) 0.5579(3) 0.81303(18) 0.0230(5) Uani 1 1 d . . .
H27 H 1.2088 0.6356 0.7613 0.028 Uiso 1 1 calc R . .
C5 C 0.6912(2) 0.6218(3) 0.39025(17) 0.0180(5) Uani 1 1 d . . .
H5 H 0.6353 0.6808 0.4189 0.022 Uiso 1 1 calc R . .
C3 C 0.8312(2) 0.5306(3) 0.58326(17) 0.0165(5) Uani 1 1 d . . .
C12 C 0.8231(2) 0.6773(2) 0.73983(17) 0.0169(5) Uani 1 1 d . . .
C7 C 0.7485(2) 0.5372(3) 0.23351(18) 0.0220(5) Uani 1 1 d . . .
H7 H 0.7287 0.5361 0.1554 0.026 Uiso 1 1 calc R . .
C10 C 1.0014(2) 0.3747(3) 0.49090(19) 0.0205(5) Uani 1 1 d . . .
H10 H 1.0551 0.3152 0.4605 0.025 Uiso 1 1 calc R . .
C6 C 0.6660(2) 0.6218(3) 0.27800(17) 0.0215(5) Uani 1 1 d . . .
H6 H 0.5922 0.6794 0.2298 0.026 Uiso 1 1 calc R . .
C28 C 0.9085(2) 0.3866(3) 0.82508(17) 0.0172(5) Uani 1 1 d . . .
C23 C 1.2051(2) 0.3496(3) 0.91173(17) 0.0202(5) Uani 1 1 d . . .
H23 H 1.1438 0.2827 0.9279 0.024 Uiso 1 1 calc R . .
C21 C 0.7584(2) 0.7747(3) 0.79159(17) 0.0190(5) Uani 1 1 d . . .
H21 H 0.8129 0.8271 0.8563 0.023 Uiso 1 1 calc R . .
C14 C 0.5986(2) 0.6123(3) 0.60310(16) 0.0163(5) Uani 1 1 d . . .
C19 C 0.5338(2) 0.7085(3) 0.65764(16) 0.0175(5) Uani 1 1 d . . .
C24 C 1.3473(2) 0.3326(3) 0.96317(18) 0.0253(6) Uani 1 1 d . . .
H24 H 1.3825 0.2549 1.0149 0.030 Uiso 1 1 calc R . .
C33 C 0.9023(2) 0.4179(3) 0.93017(18) 0.0214(5) Uani 1 1 d . . .
H33 H 0.9518 0.4997 0.9713 0.026 Uiso 1 1 calc R . .
C18 C 0.3870(2) 0.7133(3) 0.62222(18) 0.0210(5) Uani 1 1 d . . .
H18 H 0.3438 0.7809 0.6562 0.025 Uiso 1 1 calc R . .
C32 C 0.8245(2) 0.3303(3) 0.97454(19) 0.0237(5) Uani 1 1 d . . .
H32 H 0.8213 0.3523 1.0460 0.028 Uiso 1 1 calc R . .
C17 C 0.3060(2) 0.6226(3) 0.54021(19) 0.0241(5) Uani 1 1 d . . .
H17 H 0.2075 0.6280 0.5168 0.029 Uiso 1 1 calc R . .
C29 C 0.8347(2) 0.2669(3) 0.76746(19) 0.0247(5) Uani 1 1 d . . .
H29 H 0.8377 0.2437 0.6961 0.030 Uiso 1 1 calc R . .
C22 C 1.1506(2) 0.4637(3) 0.83651(17) 0.0187(5) Uani 1 1 d . . .
C25 C 1.4389(2) 0.4276(3) 0.93999(18) 0.0266(6) Uani 1 1 d . . .
H25 H 1.5365 0.4158 0.9756 0.032 Uiso 1 1 calc R . .
C31 C 0.7510(2) 0.2107(3) 0.9155(2) 0.0275(6) Uani 1 1 d . . .
H31 H 0.6978 0.1509 0.9462 0.033 Uiso 1 1 calc R . .
C30 C 0.7562(3) 0.1799(3) 0.8124(2) 0.0301(6) Uani 1 1 d . . .
H30 H 0.7058 0.0986 0.7713 0.036 Uiso 1 1 calc R . .
C26 C 1.3862(2) 0.5399(3) 0.86414(18) 0.0267(6) Uani 1 1 d . . .
H26 H 1.4480 0.6051 0.8470 0.032 Uiso 1 1 calc R . .
C11 C 1.0354(2) 0.3827(3) 0.60336(18) 0.0195(5) Uani 1 1 d . . .
H11 H 1.1155 0.3327 0.6508 0.023 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'
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
C12 N1 C1 113.47(18) . . ?
C12 N1 H1 123.3 . . ?
C1 N1 H1 123.3 . . ?
C3 C2 C11 120.87(19) . . ?
C3 C2 C1 117.19(19) . . ?
C11 C2 C1 121.94(18) . . ?
C10 C9 C8 120.8(2) . . ?
C10 C9 C4 119.63(19) . . ?
C8 C9 C4 119.55(19) . . ?
C5 C4 C9 117.62(18) . . ?
C5 C4 C3 123.63(19) . . ?
C9 C4 C3 118.66(19) . . ?
C15 C16 C17 120.5(2) . . ?
C15 C16 H16 119.7 . . ?
C17 C16 H16 119.7 . . ?
C7 C8 C9 120.7(2) . . ?
C7 C8 H8 119.7 . . ?
C9 C8 H8 119.7 . . ?
N1 C1 C22 107.12(18) . . ?
N1 C1 C2 103.63(17) . . ?
C22 C1 C2 111.68(17) . . ?
N1 C1 C28 110.31(17) . . ?
C22 C1 C28 111.91(18) . . ?
C2 C1 C28 111.77(17) . . ?
C21 C20 C19 120.7(2) . . ?
C21 C20 H20 119.6 . . ?
C19 C20 H20 119.6 . . ?
C16 C15 C14 121.6(2) . . ?
C16 C15 H15 119.2 . . ?
C14 C15 H15 119.2 . . ?
C12 C13 C14 118.10(19) . . ?
C12 C13 C3 116.09(19) . . ?
C14 C13 C3 125.67(19) . . ?
C26 C27 C22 121.0(2) . . ?
C26 C27 H27 119.5 . . ?
C22 C27 H27 119.5 . . ?
C6 C5 C4 121.2(2) . . ?
C6 C5 H5 119.4 . . ?
C4 C5 H5 119.4 . . ?
C2 C3 C4 118.95(19) . . ?
C2 C3 C13 117.30(18) . . ?
C4 C3 C13 123.33(19) . . ?
C13 C12 N1 117.41(19) . . ?
C13 C12 C21 121.2(2) . . ?
N1 C12 C21 121.37(19) . . ?
C8 C7 C6 120.3(2) . . ?
C8 C7 H7 119.9 . . ?
C6 C7 H7 119.9 . . ?
C11 C10 C9 120.4(2) . . ?
C11 C10 H10 119.8 . . ?
C9 C10 H10 119.8 . . ?
C5 C6 C7 120.6(2) . . ?
C5 C6 H6 119.7 . . ?
C7 C6 H6 119.7 . . ?
C29 C28 C33 118.2(2) . . ?
C29 C28 C1 121.9(2) . . ?
C33 C28 C1 119.9(2) . . ?
C24 C23 C22 120.8(2) . . ?
C24 C23 H23 119.6 . . ?
C22 C23 H23 119.6 . . ?
C20 C21 C12 120.2(2) . . ?
C20 C21 H21 119.9 . . ?
C12 C21 H21 119.9 . . ?
C15 C14 C19 117.59(19) . . ?
C15 C14 C13 123.4(2) . . ?
C19 C14 C13 118.85(19) . . ?
C18 C19 C20 121.4(2) . . ?
C18 C19 C14 119.4(2) . . ?
C20 C19 C14 119.20(19) . . ?
C23 C24 C25 120.7(2) . . ?
C23 C24 H24 119.7 . . ?
C25 C24 H24 119.7 . . ?
C32 C33 C28 120.4(2) . . ?
C32 C33 H33 119.8 . . ?
C28 C33 H33 119.8 . . ?
C17 C18 C19 121.4(2) . . ?
C17 C18 H18 119.3 . . ?
C19 C18 H18 119.3 . . ?
C33 C32 C31 120.6(2) . . ?
C33 C32 H32 119.7 . . ?
C31 C32 H32 119.7 . . ?
C18 C17 C16 119.4(2) . . ?
C18 C17 H17 120.3 . . ?
C16 C17 H17 120.3 . . ?
C28 C29 C30 121.0(2) . . ?
C28 C29 H29 119.5 . . ?
C30 C29 H29 119.5 . . ?
C27 C22 C23 118.1(2) . . ?
C27 C22 C1 119.3(2) . . ?
C23 C22 C1 122.6(2) . . ?
C26 C25 C24 119.0(2) . . ?
C26 C25 H25 120.5 . . ?
C24 C25 H25 120.5 . . ?
C30 C31 C32 119.2(2) . . ?
C30 C31 H31 120.4 . . ?
C32 C31 H31 120.4 . . ?
C31 C30 C29 120.5(2) . . ?
C31 C30 H30 119.7 . . ?
C29 C30 H30 119.7 . . ?
C25 C26 C27 120.4(2) . . ?
C25 C26 H26 119.8 . . ?
C27 C26 H26 119.8 . . ?
C10 C11 C2 120.8(2) . . ?
C10 C11 H11 119.6 . . ?
C2 C11 H11 119.6 . . ?
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
N1 C12 1.395(3) . ?
N1 C1 1.487(3) . ?
N1 H1 0.8800 . ?
C2 C3 1.383(3) . ?
C2 C11 1.410(3) . ?
C2 C1 1.535(3) . ?
C9 C10 1.412(3) . ?
C9 C8 1.422(3) . ?
C9 C4 1.429(3) . ?
C4 C5 1.429(3) . ?
C4 C3 1.438(3) . ?
C16 C15 1.374(3) . ?
C16 C17 1.406(3) . ?
C16 H16 0.9500 . ?
C8 C7 1.370(3) . ?
C8 H8 0.9500 . ?
C1 C22 1.526(3) . ?
C1 C28 1.538(3) . ?
C20 C21 1.358(3) . ?
C20 C19 1.424(3) . ?
C20 H20 0.9500 . ?
C15 C14 1.410(3) . ?
C15 H15 0.9500 . ?
C13 C12 1.392(3) . ?
C13 C14 1.440(3) . ?
C13 C3 1.481(3) . ?
C27 C26 1.389(3) . ?
C27 C22 1.393(3) . ?
C27 H27 0.9500 . ?
C5 C6 1.371(3) . ?
C5 H5 0.9500 . ?
C12 C21 1.408(3) . ?
C7 C6 1.406(3) . ?
C7 H7 0.9500 . ?
C10 C11 1.362(3) . ?
C10 H10 0.9500 . ?
C6 H6 0.9500 . ?
C28 C29 1.384(3) . ?
C28 C33 1.401(3) . ?
C23 C24 1.384(3) . ?
C23 C22 1.394(3) . ?
C23 H23 0.9500 . ?
C21 H21 0.9500 . ?
C14 C19 1.425(3) . ?
C19 C18 1.414(3) . ?
C24 C25 1.385(3) . ?
C24 H24 0.9500 . ?
C33 C32 1.386(3) . ?
C33 H33 0.9500 . ?
C18 C17 1.365(3) . ?
C18 H18 0.9500 . ?
C32 C31 1.388(4) . ?
C32 H32 0.9500 . ?
C17 H17 0.9500 . ?
C29 C30 1.391(3) . ?
C29 H29 0.9500 . ?
C25 C26 1.384(4) . ?
C25 H25 0.9500 . ?
C31 C30 1.372(3) . ?
C31 H31 0.9500 . ?
C30 H30 0.9500 . ?
C26 H26 0.9500 . ?
C11 H11 0.9500 . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30659290
