#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/33/4023399.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_4023399
loop_
_publ_author_name
'Jacob M. Plummer'
'Jeremy A. Weitgenant'
'Bruce C. Noll'
'Joseph W. Lauher'
'Olaf Wiest'
'Paul Helquist'
_publ_contact_author_address
;University of Notre Dame
Department of Chemistry and Biochemistry
251 Nieuwland Science Hall
Notre Dame, IN 46556-5670
USA
;
_publ_contact_author_email       Paul.Helquist.1@nd.edu
_publ_contact_author_fax         1(574)6316652
_publ_contact_author_name        'Professor Paul Helquist'
_publ_contact_author_phone       1(574)6317822
_publ_section_title
;
 Synthesis, Structure, and Metal Complexation Behavior of
 a New Type of Functionalized Chiral Phenanthroline Derivative
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              3911
_journal_page_last               3914
_journal_paper_doi               10.1021/jo702566m
_journal_volume                  73
_journal_year                    2008
_chemical_formula_sum            'C20 H24 N2 O2'
_chemical_formula_weight         324.41
_chemical_name_systematic
; 
 ? 
;
_space_group_IT_number           19
_symmetry_cell_setting           orthorhombic
_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                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   4.86670(10)
_cell_length_b                   17.2330(6)
_cell_length_c                   20.4925(8)
_cell_measurement_temperature    293(2)
_cell_volume                     1718.66(10)
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.883
_diffrn_measured_fraction_theta_max 0.883
_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  0.0477
_diffrn_reflns_av_sigmaI/netI    0.0322
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -4
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            12510
_diffrn_reflns_theta_full        28.27
_diffrn_reflns_theta_max         28.27
_diffrn_reflns_theta_min         1.54
_exptl_absorpt_coefficient_mu    0.081
_exptl_crystal_density_diffrn    1.254
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             696
_refine_diff_density_max         0.650
_refine_diff_density_min         -0.319
_refine_diff_density_rms         0.070
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0(10)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     221
_refine_ls_number_reflns         2204
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0728
_refine_ls_R_factor_gt           0.0614
_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)+(0.1312P)²+0.3466P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1789
_refine_ls_wR_factor_ref         0.1889
_reflns_number_gt                1820
_reflns_number_total             2204
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo702566m-File004.cif
_cod_data_source_block           bcn241_01
_cod_database_code               4023399
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
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
N1 N 0.0791(7) 0.41903(15) 0.01451(14) 0.0257(7) Uani 1 1 d . . .
N2 N 0.4808(6) 0.52382(14) -0.01372(12) 0.0209(6) Uani 1 1 d . . .
O1 O -0.4969(8) 0.45667(16) 0.12071(14) 0.0497(8) Uani 1 1 d . . .
H1 H -0.5552 0.4649 0.0838 0.075 Uiso 1 1 calc R . .
O2 O 0.6387(6) 0.73253(13) 0.03200(12) 0.0282(6) Uani 1 1 d . . .
H2 H 0.7760 0.7480 0.0128 0.042 Uiso 1 1 calc R . .
C1 C -0.1190(9) 0.3692(2) 0.02924(18) 0.0300(9) Uani 1 1 d . . .
C2 C -0.2822(9) 0.33328(18) -0.0191(2) 0.0316(9) Uani 1 1 d . . .
H2A H -0.4161 0.2974 -0.0074 0.038 Uiso 1 1 calc R . .
C3 C -0.2414(8) 0.35175(19) -0.08356(19) 0.0291(9) Uani 1 1 d . . .
H3 H -0.3480 0.3286 -0.1158 0.035 Uiso 1 1 calc R . .
C4 C -0.0373(9) 0.40597(18) -0.10049(16) 0.0273(8) Uani 1 1 d . . .
C5 C 0.0162(9) 0.42959(19) -0.16646(16) 0.0287(8) Uani 1 1 d . . .
H5 H -0.0822 0.4070 -0.2004 0.034 Uiso 1 1 calc R . .
C6 C 0.2071(9) 0.48405(19) -0.17999(16) 0.0305(9) Uani 1 1 d . . .
H6 H 0.2369 0.4986 -0.2231 0.037 Uiso 1 1 calc R . .
C7 C 0.3643(8) 0.51975(18) -0.12934(16) 0.0252(8) Uani 1 1 d . . .
C8 C 0.5627(9) 0.57730(18) -0.14055(16) 0.0300(9) Uani 1 1 d . . .
H8 H 0.5898 0.5958 -0.1827 0.036 Uiso 1 1 calc R . .
C9 C 0.7168(8) 0.60659(19) -0.09053(17) 0.0271(8) Uani 1 1 d . . .
H9 H 0.8463 0.6453 -0.0981 0.032 Uiso 1 1 calc R . .
C10 C 0.6745(8) 0.57659(17) -0.02682(16) 0.0248(8) Uani 1 1 d . . .
C11 C 0.3273(7) 0.49574(16) -0.06385(15) 0.0221(7) Uani 1 1 d . . .
C12 C 0.1186(8) 0.43840(17) -0.04920(16) 0.0223(7) Uani 1 1 d . . .
C13 C -0.1599(10) 0.3538(2) 0.1020(2) 0.0407(10) Uani 1 1 d . . .
H13A H -0.1297 0.2990 0.1102 0.049 Uiso 1 1 calc R . .
H13B H -0.0216 0.3824 0.1262 0.049 Uiso 1 1 calc R . .
C14 C -0.4386(10) 0.3756(2) 0.12797(19) 0.0397(10) Uani 1 1 d . . .
H14 H -0.5798 0.3453 0.1053 0.048 Uiso 1 1 calc R . .
C15 C -0.4601(12) 0.3611(2) 0.20164(19) 0.0434(11) Uani 1 1 d . . .
H15A H -0.3419 0.3979 0.2239 0.052 Uiso 1 1 calc R . .
H15B H -0.6474 0.3715 0.2153 0.052 Uiso 1 1 calc R . .
C16 C -0.3850(14) 0.2818(2) 0.2230(2) 0.0564(14) Uani 1 1 d . . .
H16A H -0.1954 0.2721 0.2129 0.085 Uiso 1 1 calc R . .
H16B H -0.4982 0.2447 0.2008 0.085 Uiso 1 1 calc R . .
H16C H -0.4125 0.2772 0.2692 0.085 Uiso 1 1 calc R . .
C17 C 0.8474(8) 0.60330(18) 0.02934(16) 0.0263(8) Uani 1 1 d . . .
H17A H 1.0194 0.6237 0.0126 0.032 Uiso 1 1 calc R . .
H17B H 0.8901 0.5591 0.0568 0.032 Uiso 1 1 calc R . .
C18 C 0.7082(8) 0.66533(19) 0.07050(16) 0.0264(8) Uani 1 1 d . . .
H18 H 0.5365 0.6434 0.0873 0.032 Uiso 1 1 calc R . .
C19 C 0.8833(10) 0.6893(2) 0.12912(18) 0.0351(9) Uani 1 1 d . . .
H19A H 1.0556 0.7104 0.1133 0.042 Uiso 1 1 calc R . .
H19B H 0.7887 0.7302 0.1525 0.042 Uiso 1 1 calc R . .
C20 C 0.9454(13) 0.6237(3) 0.1764(2) 0.0539(13) Uani 1 1 d . . .
H20A H 1.0574 0.5855 0.1551 0.081 Uiso 1 1 calc R . .
H20B H 0.7765 0.6003 0.1904 0.081 Uiso 1 1 calc R . .
H20C H 1.0416 0.6439 0.2136 0.081 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 0.0000 '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 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0000 '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
C1 N1 C12 118.7(3) . . ?
C10 N2 C11 118.5(3) . . ?
C14 O1 H1 109.5 . . ?
C18 O2 H2 109.5 . . ?
N1 C1 C2 122.2(3) . . ?
N1 C1 C13 115.4(4) . . ?
C2 C1 C13 122.4(4) . . ?
C3 C2 C1 119.5(3) . . ?
C3 C2 H2A 120.3 . . ?
C1 C2 H2A 120.3 . . ?
C2 C3 C4 119.5(3) . . ?
C2 C3 H3 120.2 . . ?
C4 C3 H3 120.2 . . ?
C3 C4 C12 117.3(3) . . ?
C3 C4 C5 123.3(3) . . ?
C12 C4 C5 119.4(3) . . ?
C6 C5 C4 121.0(3) . . ?
C6 C5 H5 119.5 . . ?
C4 C5 H5 119.5 . . ?
C5 C6 C7 121.3(3) . . ?
C5 C6 H6 119.4 . . ?
C7 C6 H6 119.4 . . ?
C8 C7 C11 116.7(3) . . ?
C8 C7 C6 123.6(3) . . ?
C11 C7 C6 119.6(3) . . ?
C9 C8 C7 121.0(3) . . ?
C9 C8 H8 119.5 . . ?
C7 C8 H8 119.5 . . ?
C8 C9 C10 118.4(3) . . ?
C8 C9 H9 120.8 . . ?
C10 C9 H9 120.8 . . ?
N2 C10 C9 122.3(3) . . ?
N2 C10 C17 116.8(3) . . ?
C9 C10 C17 120.9(3) . . ?
N2 C11 C7 122.8(3) . . ?
N2 C11 C12 118.1(3) . . ?
C7 C11 C12 119.0(3) . . ?
N1 C12 C4 122.8(3) . . ?
N1 C12 C11 117.7(3) . . ?
C4 C12 C11 119.5(3) . . ?
C14 C13 C1 114.7(4) . . ?
C14 C13 H13A 108.6 . . ?
C1 C13 H13A 108.6 . . ?
C14 C13 H13B 108.6 . . ?
C1 C13 H13B 108.6 . . ?
H13A C13 H13B 107.6 . . ?
O1 C14 C13 112.7(4) . . ?
O1 C14 C15 104.3(3) . . ?
C13 C14 C15 111.6(4) . . ?
O1 C14 H14 109.4 . . ?
C13 C14 H14 109.4 . . ?
C15 C14 H14 109.4 . . ?
C16 C15 C14 115.1(4) . . ?
C16 C15 H15A 108.5 . . ?
C14 C15 H15A 108.5 . . ?
C16 C15 H15B 108.5 . . ?
C14 C15 H15B 108.5 . . ?
H15A C15 H15B 107.5 . . ?
C15 C16 H16A 109.5 . . ?
C15 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C15 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C10 C17 C18 113.1(3) . . ?
C10 C17 H17A 109.0 . . ?
C18 C17 H17A 109.0 . . ?
C10 C17 H17B 109.0 . . ?
C18 C17 H17B 109.0 . . ?
H17A C17 H17B 107.8 . . ?
O2 C18 C17 111.4(3) . . ?
O2 C18 C19 110.1(3) . . ?
C17 C18 C19 112.1(3) . . ?
O2 C18 H18 107.6 . . ?
C17 C18 H18 107.6 . . ?
C19 C18 H18 107.6 . . ?
C20 C19 C18 114.3(3) . . ?
C20 C19 H19A 108.7 . . ?
C18 C19 H19A 108.7 . . ?
C20 C19 H19B 108.7 . . ?
C18 C19 H19B 108.7 . . ?
H19A C19 H19B 107.6 . . ?
C19 C20 H20A 109.5 . . ?
C19 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C19 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 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
N1 C1 1.326(5) . ?
N1 C12 1.361(4) . ?
N2 C10 1.337(4) . ?
N2 C11 1.359(4) . ?
O1 C14 1.433(5) . ?
O1 H1 0.8200 . ?
O2 C18 1.441(4) . ?
O2 H2 0.8200 . ?
C1 C2 1.413(6) . ?
C1 C13 1.528(5) . ?
C2 C3 1.373(5) . ?
C2 H2A 0.9300 . ?
C3 C4 1.407(5) . ?
C3 H3 0.9300 . ?
C4 C12 1.412(5) . ?
C4 C5 1.436(5) . ?
C5 C6 1.349(5) . ?
C5 H5 0.9300 . ?
C6 C7 1.429(5) . ?
C6 H6 0.9300 . ?
C7 C8 1.403(5) . ?
C7 C11 1.416(4) . ?
C8 C9 1.367(5) . ?
C8 H8 0.9300 . ?
C9 C10 1.419(4) . ?
C9 H9 0.9300 . ?
C10 C17 1.498(5) . ?
C11 C12 1.449(5) . ?
C13 C14 1.505(7) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.534(5) . ?
C14 H14 0.9800 . ?
C15 C16 1.481(6) . ?
C15 H15A 0.9700 . ?
C15 H15B 0.9700 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 C18 1.521(5) . ?
C17 H17A 0.9700 . ?
C17 H17B 0.9700 . ?
C18 C19 1.529(5) . ?
C18 H18 0.9800 . ?
C19 C20 1.519(6) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 21194756
