#------------------------------------------------------------------------------
#$Date: 2019-03-05 10:52:05 +0200 (Tue, 05 Mar 2019) $
#$Revision: 213973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/20/44/7204450.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_7204450
loop_
_publ_author_name
'Lu, Jun'
'Xu, Xuenong'
'Wang, Shaozhong'
'Wang, Cunde'
'Hu, Yuefei'
'Hu, Hongwen'
_publ_section_title
;
 Novel preparation of non-racemic
 1-[??-(1-azacycloalkyl)benzyl]-2-naphthols from Betti base and their
 application as chiral ligands in the asymmetric addition of
 diethylzinc to aryl aldehydes
;
_journal_issue                   24
_journal_name_full
'Journal of the Chemical Society, Perkin Transactions 1'
_journal_page_first              2900
_journal_paper_doi               10.1039/b204534f
_journal_year                    2002
_chemical_formula_sum            'C22 H20 N O'
_chemical_formula_weight         314.39
_space_group_IT_number           19
_symmetry_space_group_name_Hall  'P 2ac 2ab'
_symmetry_space_group_name_H-M   'P 21 21 21'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.813(4)
_cell_length_b                   10.354(3)
_cell_length_c                   16.491(4)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    295(2)
_cell_measurement_theta_max      14.60
_cell_measurement_theta_min      11.12
_cell_volume                     1675.5(9)
_computing_cell_refinement       'CAD4, Enraf-Nonius'
_computing_data_collection       'CAD4, Enraf-Nonius'
_computing_molecular_graphics    'ORTEP-3 for Windows V1.05(Farrugia, 1999)'
_computing_publication_material  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      295(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  CAD4
_diffrn_measurement_method       'omega/2-theta scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0000
_diffrn_reflns_av_sigmaI/netI    0.0373
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       0
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2135
_diffrn_reflns_theta_full        27.17
_diffrn_reflns_theta_max         27.17
_diffrn_reflns_theta_min         2.32
_diffrn_standards_interval_time  3600
_diffrn_standards_number         100
_exptl_absorpt_coefficient_mu    0.076
_exptl_absorpt_correction_T_max  0.9776
_exptl_absorpt_correction_T_min  0.9703
_exptl_absorpt_correction_type   'North, Phillips & Mathews, 1968'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.246
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             668
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.30
_refine_diff_density_max         0.179
_refine_diff_density_min         -0.144
_refine_diff_density_rms         0.035
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   -10(3)
_refine_ls_extinction_coef       0.0143(17)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.043
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     218
_refine_ls_number_reflns         2135
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.043
_refine_ls_R_factor_all          0.0788
_refine_ls_R_factor_gt           0.0334
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0425P)²+0.2770P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0827
_refine_ls_wR_factor_ref         0.0997
_reflns_number_gt                1384
_reflns_number_total             2135
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            b204534f.txt
_cod_data_source_block           lu0112
_cod_database_code               7204450
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -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
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C -0.0009(3) 0.4151(3) 0.22956(15) 0.0463(6) Uani 1 d . . .
H1 H 0.0566 0.3522 0.2508 0.056 Uiso 1 calc R . .
C2 C -0.1326(3) 0.4230(3) 0.25647(18) 0.0576(8) Uani 1 d . . .
H2 H -0.1639 0.3649 0.2952 0.069 Uiso 1 calc R . .
C3 C -0.2204(3) 0.5175(3) 0.22625(19) 0.0621(8) Uani 1 d . . .
H3 H -0.3099 0.5218 0.2446 0.075 Uiso 1 calc R . .
C4 C -0.1753(3) 0.6034(3) 0.17009(17) 0.0559(8) Uani 1 d . . .
H4 H -0.2344 0.6665 0.1507 0.067 Uiso 1 calc R . .
C5 C 0.0074(3) 0.6859(3) 0.08156(16) 0.0470(7) Uani 1 d . . .
H5 H -0.0498 0.7511 0.0630 0.056 Uiso 1 calc R . .
C6 C 0.1356(3) 0.6763(2) 0.05139(16) 0.0457(6) Uani 1 d . . .
H6 H 0.1651 0.7338 0.0118 0.055 Uiso 1 calc R . .
C7 C 0.2241(2) 0.5791(2) 0.07989(15) 0.0384(6) Uani 1 d . . .
C8 C 0.1849(2) 0.4939(2) 0.13859(14) 0.0355(5) Uani 1 d . . .
C9 C -0.0402(3) 0.5987(3) 0.14050(15) 0.0429(6) Uani 1 d . . .
C10 C 0.0494(2) 0.5016(3) 0.16978(14) 0.0373(5) Uani 1 d . . .
C11 C 0.2850(2) 0.3905(2) 0.16510(14) 0.0357(5) Uani 1 d . . .
H11 H 0.2329 0.3110 0.1742 0.043 Uiso 1 calc R . .
C12 C 0.3595(2) 0.4216(3) 0.24378(14) 0.0367(5) Uani 1 d . . .
C13 C 0.3465(3) 0.5386(3) 0.28300(16) 0.0484(7) Uani 1 d . . .
H13 H 0.2889 0.6015 0.2619 0.058 Uiso 1 calc R . .
C14 C 0.4189(3) 0.5635(3) 0.35389(16) 0.0569(8) Uani 1 d . . .
H14 H 0.4099 0.6431 0.3794 0.068 Uiso 1 calc R . .
C15 C 0.5023(3) 0.4723(3) 0.38601(16) 0.0591(8) Uani 1 d . . .
H15 H 0.5502 0.4894 0.4335 0.071 Uiso 1 calc R . .
C16 C 0.5160(3) 0.3543(3) 0.34817(17) 0.0570(8) Uani 1 d . . .
H16 H 0.5725 0.2914 0.3703 0.068 Uiso 1 calc R . .
C17 C 0.4455(3) 0.3295(3) 0.27722(16) 0.0463(6) Uani 1 d . . .
H17 H 0.4558 0.2501 0.2516 0.056 Uiso 1 calc R . .
O1 O 0.34912(17) 0.57680(17) 0.04290(11) 0.0473(5) Uani 1 d . . .
C18 C 0.3208(3) 0.2902(3) 0.03275(15) 0.0443(6) Uani 1 d . . .
H18A H 0.2437 0.3382 0.0116 0.053 Uiso 1 calc R . .
H18B H 0.2870 0.2087 0.0536 0.053 Uiso 1 calc R . .
C19 C 0.4207(3) 0.2642(3) -0.03526(16) 0.0523(7) Uani 1 d . . .
H19A H 0.4914 0.2061 -0.0162 0.063 Uiso 1 calc R . .
H19B H 0.3737 0.2224 -0.0799 0.063 Uiso 1 calc R . .
C20 C 0.4847(3) 0.3881(3) -0.06460(16) 0.0563(8) Uani 1 d . . .
H20A H 0.4158 0.4418 -0.0900 0.068 Uiso 1 calc R . .
H20B H 0.5540 0.3688 -0.1047 0.068 Uiso 1 calc R . .
C21 C 0.5484(3) 0.4603(3) 0.00610(16) 0.0498(7) Uani 1 d . . .
H21A H 0.6252 0.4113 0.0267 0.060 Uiso 1 calc R . .
H21B H 0.5822 0.5431 -0.0127 0.060 Uiso 1 calc R . .
C22 C 0.4467(3) 0.4819(2) 0.07397(16) 0.0409(6) Uani 1 d . . .
H22 H 0.4947 0.5197 0.1204 0.049 Uiso 1 calc R . .
N1 N 0.38375(19) 0.36399(19) 0.09938(11) 0.0361(5) Uani 1 d . . .
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
C2 C1 C10 121.0(3) . . ?
C2 C1 H1 119.5 . . ?
C10 C1 H1 119.5 . . ?
C1 C2 C3 120.6(3) . . ?
C1 C2 H2 119.7 . . ?
C3 C2 H2 119.7 . . ?
C4 C3 C2 120.1(3) . . ?
C4 C3 H3 119.9 . . ?
C2 C3 H3 119.9 . . ?
C3 C4 C9 121.2(3) . . ?
C3 C4 H4 119.4 . . ?
C9 C4 H4 119.4 . . ?
C6 C5 C9 121.0(2) . . ?
C6 C5 H5 119.5 . . ?
C9 C5 H5 119.5 . . ?
C5 C6 C7 120.1(2) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 H6 119.9 . . ?
C8 C7 O1 123.8(2) . . ?
C8 C7 C6 121.6(2) . . ?
O1 C7 C6 114.6(2) . . ?
C7 C8 C10 118.8(2) . . ?
C7 C8 C11 118.6(2) . . ?
C10 C8 C11 122.6(2) . . ?
C5 C9 C4 121.9(3) . . ?
C5 C9 C10 118.9(2) . . ?
C4 C9 C10 119.2(3) . . ?
C9 C10 C1 117.9(2) . . ?
C9 C10 C8 119.6(2) . . ?
C1 C10 C8 122.5(2) . . ?
N1 C11 C8 110.11(19) . . ?
N1 C11 C12 110.42(18) . . ?
C8 C11 C12 114.0(2) . . ?
N1 C11 H11 107.3 . . ?
C8 C11 H11 107.3 . . ?
C12 C11 H11 107.3 . . ?
C13 C12 C17 118.3(2) . . ?
C13 C12 C11 122.7(2) . . ?
C17 C12 C11 119.0(2) . . ?
C12 C13 C14 120.6(3) . . ?
C12 C13 H13 119.7 . . ?
C14 C13 H13 119.7 . . ?
C15 C14 C13 120.5(3) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C14 C15 C16 119.9(3) . . ?
C14 C15 H15 120.0 . . ?
C16 C15 H15 120.0 . . ?
C15 C16 C17 119.9(3) . . ?
C15 C16 H16 120.1 . . ?
C17 C16 H16 120.1 . . ?
C16 C17 C12 120.9(3) . . ?
C16 C17 H17 119.6 . . ?
C12 C17 H17 119.6 . . ?
C7 O1 C22 116.20(19) . . ?
N1 C18 C19 111.9(2) . . ?
N1 C18 H18A 109.2 . . ?
C19 C18 H18A 109.2 . . ?
N1 C18 H18B 109.2 . . ?
C19 C18 H18B 109.2 . . ?
H18A C18 H18B 107.9 . . ?
C20 C19 C18 110.8(2) . . ?
C20 C19 H19A 109.5 . . ?
C18 C19 H19A 109.5 . . ?
C20 C19 H19B 109.5 . . ?
C18 C19 H19B 109.5 . . ?
H19A C19 H19B 108.1 . . ?
C19 C20 C21 110.1(2) . . ?
C19 C20 H20A 109.6 . . ?
C21 C20 H20A 109.6 . . ?
C19 C20 H20B 109.6 . . ?
C21 C20 H20B 109.6 . . ?
H20A C20 H20B 108.2 . . ?
C22 C21 C20 111.6(2) . . ?
C22 C21 H21A 109.3 . . ?
C20 C21 H21A 109.3 . . ?
C22 C21 H21B 109.3 . . ?
C20 C21 H21B 109.3 . . ?
H21A C21 H21B 108.0 . . ?
N1 C22 O1 113.12(19) . . ?
N1 C22 C21 112.0(2) . . ?
O1 C22 C21 105.7(2) . . ?
N1 C22 H22 108.6 . . ?
O1 C22 H22 108.6 . . ?
C21 C22 H22 108.6 . . ?
C22 N1 C18 113.9(2) . . ?
C22 N1 C11 109.82(18) . . ?
C18 N1 C11 111.58(18) . . ?
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 C2 1.369(4) . ?
C1 C10 1.420(4) . ?
C1 H1 0.9300 . ?
C2 C3 1.396(4) . ?
C2 H2 0.9300 . ?
C3 C4 1.358(4) . ?
C3 H3 0.9300 . ?
C4 C9 1.413(4) . ?
C4 H4 0.9300 . ?
C5 C6 1.356(4) . ?
C5 C9 1.406(4) . ?
C5 H5 0.9300 . ?
C6 C7 1.410(3) . ?
C6 H6 0.9300 . ?
C7 C8 1.365(3) . ?
C7 O1 1.370(3) . ?
C8 C10 1.428(3) . ?
C8 C11 1.517(3) . ?
C9 C10 1.420(4) . ?
C11 N1 1.479(3) . ?
C11 C12 1.524(3) . ?
C11 H11 0.9800 . ?
C12 C13 1.379(4) . ?
C12 C17 1.387(3) . ?
C13 C14 1.392(4) . ?
C13 H13 0.9300 . ?
C14 C15 1.357(4) . ?
C14 H14 0.9300 . ?
C15 C16 1.379(4) . ?
C15 H15 0.9300 . ?
C16 C17 1.383(4) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
O1 C22 1.464(3) . ?
C18 N1 1.474(3) . ?
C18 C19 1.514(3) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 C20 1.508(4) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 C21 1.520(4) . ?
C20 H20A 0.9700 . ?
C20 H20B 0.9700 . ?
C21 C22 1.516(3) . ?
C21 H21A 0.9700 . ?
C21 H21B 0.9700 . ?
C22 N1 1.431(3) . ?
C22 H22 0.9800 . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9567803
