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#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/2/22/77/2227724.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_2227724
loop_
_publ_author_name
'Bernès, Sylvain'
'Hernández, Guadalupe'
'Vázquez, Jaime'
'Tovar, Alejandra'
'Gutiérrez, René'
_publ_section_title
;
 (--)-(S)-N,N'-Bis[1-(1-naphthyl)ethyl]oxalamide
;
_journal_coeditor_code           JH2225
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2988
_journal_paper_doi               10.1107/S1600536810043424
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C26 H24 N2 O2'
_chemical_formula_moiety         'C26 H24 N2 O2'
_chemical_formula_sum            'C26 H24 N2 O2'
_chemical_formula_weight         396.47
_chemical_melting_point          513
_chemical_name_systematic
;
(-)-(S)-N,N'-Bis[1-(1-naphthyl)ethyl]ethanediamide
;
_space_group_IT_number           178
_symmetry_cell_setting           hexagonal
_symmetry_space_group_name_Hall  'P 61 2 (0 0 5)'
_symmetry_space_group_name_H-M   'P 61 2 2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXTL-Plus
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                120.00
_cell_formula_units_Z            6
_cell_length_a                   11.4489(11)
_cell_length_b                   11.4489(11)
_cell_length_c                   28.350(4)
_cell_measurement_reflns_used    67
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      11.89
_cell_measurement_theta_min      4.11
_cell_volume                     3218.2(6)
_computing_cell_refinement       'XSCANS (Siemens, 1996)'
_computing_data_collection       'XSCANS (Siemens, 1996)'
_computing_data_reduction        'XSCANS (Siemens, 1996)'
_computing_molecular_graphics    'Mercury (Macrae et al., 2006)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298.0(10)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Siemens P4'
_diffrn_measurement_method       'ω 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  0.0569
_diffrn_reflns_av_sigmaI/netI    0.0378
_diffrn_reflns_limit_h_max       2
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -1
_diffrn_reflns_limit_l_max       1
_diffrn_reflns_limit_l_min       -33
_diffrn_reflns_number            5314
_diffrn_reflns_theta_full        25.05
_diffrn_reflns_theta_max         25.05
_diffrn_reflns_theta_min         2.05
_diffrn_standards_decay_%        1
_diffrn_standards_interval_count 97
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.078
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.227
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             1260
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.22
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.122
_refine_diff_density_min         -0.140
_refine_ls_extinction_coef       0.011(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXL97 (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.112
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     141
_refine_ls_number_reflns         1208
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.112
_refine_ls_R_factor_all          0.0871
_refine_ls_R_factor_gt           0.0431
_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)+(0.0649P)²+0.2213P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1023
_refine_ls_wR_factor_ref         0.1384
_reflns_number_gt                730
_reflns_number_total             1208
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            jh2225.cif
_cod_data_source_block           I
_cod_original_cell_volume        3218.2(7)
_cod_original_sg_symbol_Hall     'P 61 2 (0 0 -1)'
_cod_database_code               2227724
_cod_database_fobs_code          2227724
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-y, x-y, z+1/3'
'-x+y, -x, z+2/3'
'-x, -y, z+1/2'
'y, -x+y, z+5/6'
'x-y, x, z+1/6'
'y, x, -z+1/3'
'x-y, -y, -z'
'-x, -x+y, -z+2/3'
'-y, -x, -z+5/6'
'-x+y, y, -z+1/2'
'x, x-y, -z+1/6'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.1760(3) 0.1496(2) 0.53227(7) 0.0718(8) Uani d . 1 . .
C C1 0.1517(3) 0.0760(3) 0.49767(11) 0.0539(8) Uani d . 1 . .
N N2 0.1898(3) 0.1213(3) 0.45411(9) 0.0594(8) Uani d D 1 . .
H H2 0.168(3) 0.058(3) 0.4311(9) 0.071 Uiso d D 1 . .
C C3 0.2678(3) 0.2653(3) 0.44315(11) 0.0589(9) Uani d . 1 . .
H H3A 0.3249 0.3110 0.4705 0.071 Uiso calc R 1 . .
C C4 0.3604(4) 0.2880(4) 0.40144(13) 0.0852(13) Uani d . 1 . .
H H4B 0.4194 0.2535 0.4088 0.128 Uiso calc R 1 . .
H H4C 0.4131 0.3828 0.3949 0.128 Uiso calc R 1 . .
H H4D 0.3072 0.2420 0.3743 0.128 Uiso calc R 1 . .
C C5 0.1787(4) 0.3254(4) 0.43491(11) 0.0632(10) Uani d . 1 . .
C C6 0.0662(4) 0.2582(5) 0.40749(15) 0.0878(12) Uani d . 1 . .
H H6A 0.0436 0.1736 0.3957 0.105 Uiso calc R 1 . .
C C7 -0.0158(6) 0.3123(7) 0.39661(18) 0.1117(17) Uani d . 1 . .
H H7A -0.0907 0.2651 0.3773 0.134 Uiso calc R 1 . .
C C8 0.0142(6) 0.4343(7) 0.4144(2) 0.1100(17) Uani d . 1 . .
H H8B -0.0420 0.4692 0.4079 0.132 Uiso calc R 1 . .
C C9 0.1289(6) 0.5082(5) 0.44246(16) 0.0855(13) Uani d . 1 . .
C C10 0.1624(8) 0.6363(6) 0.4601(2) 0.119(2) Uani d . 1 . .
H H10B 0.1074 0.6721 0.4529 0.143 Uiso calc R 1 . .
C C11 0.2721(8) 0.7080(6) 0.4873(2) 0.126(2) Uani d . 1 . .
H H11D 0.2911 0.7913 0.4993 0.151 Uiso calc R 1 . .
C C12 0.3575(6) 0.6564(5) 0.49739(19) 0.1110(17) Uani d . 1 . .
H H12B 0.4343 0.7068 0.5156 0.133 Uiso calc R 1 . .
C C13 0.3293(5) 0.5332(4) 0.48084(13) 0.0781(12) Uani d . 1 . .
H H13B 0.3868 0.5003 0.4881 0.094 Uiso calc R 1 . .
C C14 0.2145(4) 0.4552(4) 0.45291(12) 0.0660(10) Uani d . 1 . .
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_
_diffrn_standard_refln_index_h
_diffrn_standard_refln_index_k
_diffrn_standard_refln_index_l
2 0 -1
-1 1 5
0 -2 1
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 C1 N2 . . 123.8(3) ?
O1 C1 C1 . 8_556 121.4(4) ?
N2 C1 C1 . 8_556 114.8(3) ?
C1 N2 C3 . . 122.3(3) ?
C1 N2 H2 . . 117(2) ?
C3 N2 H2 . . 121(2) ?
N2 C3 C5 . . 112.1(3) ?
N2 C3 C4 . . 109.8(3) ?
C5 C3 C4 . . 112.0(3) ?
N2 C3 H3A . . 107.6 ?
C5 C3 H3A . . 107.6 ?
C4 C3 H3A . . 107.6 ?
C3 C4 H4B . . 109.5 ?
C3 C4 H4C . . 109.5 ?
H4B C4 H4C . . 109.5 ?
C3 C4 H4D . . 109.5 ?
H4B C4 H4D . . 109.5 ?
H4C C4 H4D . . 109.5 ?
C6 C5 C14 . . 119.4(4) ?
C6 C5 C3 . . 119.6(3) ?
C14 C5 C3 . . 120.9(3) ?
C5 C6 C7 . . 122.0(5) ?
C5 C6 H6A . . 119.0 ?
C7 C6 H6A . . 119.0 ?
C8 C7 C6 . . 119.6(5) ?
C8 C7 H7A . . 120.2 ?
C6 C7 H7A . . 120.2 ?
C7 C8 C9 . . 120.8(5) ?
C7 C8 H8B . . 119.6 ?
C9 C8 H8B . . 119.6 ?
C8 C9 C10 . . 121.0(6) ?
C8 C9 C14 . . 120.0(4) ?
C10 C9 C14 . . 119.0(5) ?
C11 C10 C9 . . 121.5(6) ?
C11 C10 H10B . . 119.2 ?
C9 C10 H10B . . 119.2 ?
C10 C11 C12 . . 119.6(6) ?
C10 C11 H11D . . 120.2 ?
C12 C11 H11D . . 120.2 ?
C13 C12 C11 . . 120.8(6) ?
C13 C12 H12B . . 119.6 ?
C11 C12 H12B . . 119.6 ?
C12 C13 C14 . . 120.9(5) ?
C12 C13 H13B . . 119.6 ?
C14 C13 H13B . . 119.6 ?
C13 C14 C9 . . 118.2(4) ?
C13 C14 C5 . . 123.7(4) ?
C9 C14 C5 . . 118.1(4) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
O1 C1 . 1.231(4) ?
C1 N2 . 1.326(4) ?
C1 C1 8_556 1.512(7) ?
N2 C3 . 1.463(4) ?
N2 H2 . 0.911(10) ?
C3 C5 . 1.506(5) ?
C3 C4 . 1.522(5) ?
C3 H3A . 0.9800 ?
C4 H4B . 0.9600 ?
C4 H4C . 0.9600 ?
C4 H4D . 0.9600 ?
C5 C6 . 1.366(5) ?
C5 C14 . 1.424(5) ?
C6 C7 . 1.394(6) ?
C6 H6A . 0.9300 ?
C7 C8 . 1.358(7) ?
C7 H7A . 0.9300 ?
C8 C9 . 1.400(7) ?
C8 H8B . 0.9300 ?
C9 C10 . 1.409(7) ?
C9 C14 . 1.418(6) ?
C10 C11 . 1.348(8) ?
C10 H10B . 0.9300 ?
C11 C12 . 1.401(7) ?
C11 H11D . 0.9300 ?
C12 C13 . 1.363(6) ?
C12 H12B . 0.9300 ?
C13 C14 . 1.406(6) ?
C13 H13B . 0.9300 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_publ_flag
N2 H2 O1 5_554 0.911(10) 2.055(15) 2.931(3) 161(3) y
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O1 C1 N2 C3 . . . . 1.3(5) ?
O1 C1 C1 O1 . . 8_556 8_556 164.3(5) ?
C1 C1 N2 C3 8_556 . . . -178.1(2) ?
C1 N2 C3 C5 . . . . -86.9(4) ?
C1 N2 C3 C4 . . . . 148.0(3) ?
N2 C3 C5 C6 . . . . -44.7(4) ?
N2 C1 C1 N2 . . 8_556 8_556 163.2(5) ?
C4 C3 C5 C6 . . . . 79.2(4) ?
N2 C3 C5 C14 . . . . 139.2(3) ?
C4 C3 C5 C14 . . . . -96.9(4) ?
C14 C5 C6 C7 . . . . -0.3(6) ?
C3 C5 C6 C7 . . . . -176.5(4) ?
C5 C6 C7 C8 . . . . -1.5(8) ?
C6 C7 C8 C9 . . . . 1.9(8) ?
C7 C8 C9 C10 . . . . 178.5(5) ?
C7 C8 C9 C14 . . . . -0.6(7) ?
C8 C9 C10 C11 . . . . 179.7(5) ?
C14 C9 C10 C11 . . . . -1.2(7) ?
C9 C10 C11 C12 . . . . 1.7(8) ?
C10 C11 C12 C13 . . . . -1.4(8) ?
C11 C12 C13 C14 . . . . 0.5(7) ?
C12 C13 C14 C9 . . . . 0.0(5) ?
C12 C13 C14 C5 . . . . -179.4(4) ?
C8 C9 C14 C13 . . . . 179.4(4) ?
C10 C9 C14 C13 . . . . 0.3(5) ?
C8 C9 C14 C5 . . . . -1.2(5) ?
C10 C9 C14 C5 . . . . 179.8(4) ?
C6 C5 C14 C13 . . . . -179.0(3) ?
C3 C5 C14 C13 . . . . -2.9(5) ?
C6 C5 C14 C9 . . . . 1.6(5) ?
C3 C5 C14 C9 . . . . 177.7(3) ?
