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#$Date: 2016-03-21 03:09:59 +0200 (Mon, 21 Mar 2016) $
#$Revision: 178423 $
#$URL: svn://www.crystallography.net/cod/cif/4/02/44/4024412.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_4024412
loop_
_publ_author_name
'Dusan Hesek'
'Mijoon Lee'
'Bruce C. Noll'
'Jed F. Fisher'
'Shahriar Mobashery'
_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       mobashery@nd.edu
_publ_contact_author_fax         1(574)6316652
_publ_contact_author_name        'Professor Shahriar Mobashery'
_publ_contact_author_phone       1(574)6312933
_publ_section_title
;
Complications from Dual Roles of Sodium Hydride as a Base and as a Reducing
Agent
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2567
_journal_page_last               2570
_journal_paper_doi               10.1021/jo802706d
_journal_volume                  74
_journal_year                    2009
_chemical_compound_source        synthesized
_chemical_formula_moiety         'C18 H20 N2'
_chemical_formula_sum            'C18 H20 N2'
_chemical_formula_weight         264.36
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_Int_Tables_number      2
_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                111.414(2)
_cell_angle_beta                 99.719(2)
_cell_angle_gamma                91.631(2)
_cell_formula_units_Z            2
_cell_length_a                   9.0162(4)
_cell_length_b                   9.5201(4)
_cell_length_c                   9.5212(4)
_cell_measurement_reflns_used    5902
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      68.7441
_cell_measurement_theta_min      5.0008
_cell_volume                     746.29(6)
_computing_cell_refinement       'APEX2/SAINT (Bruker, 2007)'
_computing_data_collection       'APEX2 (Bruker, 2007)'
_computing_data_reduction        'SAINT/XPREP (Bruker, 2007; Sheldrick, 2008)'
_computing_molecular_graphics    'XP (Sheldrick, 2008)'
_computing_publication_material  'XCIF (Sheldrick, 2008)/enCIFer (CCDC, 2005)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XS (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 0.937
_diffrn_measured_fraction_theta_max 0.937
_diffrn_measurement_device_type  'Bruker SMART Apex CCD diffractometer'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0158
_diffrn_reflns_av_sigmaI/netI    0.0161
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            9428
_diffrn_reflns_theta_full        69.46
_diffrn_reflns_theta_max         69.46
_diffrn_reflns_theta_min         5.00
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              'Siemens KFCU2K-90'
_exptl_absorpt_coefficient_mu    0.530
_exptl_absorpt_correction_T_max  0.97
_exptl_absorpt_correction_T_min  0.92
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'Sheldrick, G. M. (2008) SADABS. UNiversity of Göttingen, Germany.'
_exptl_crystal_colour            'clear colorless'
_exptl_crystal_density_diffrn    1.176
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             284
_exptl_crystal_size_max          0.16
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.239
_refine_diff_density_min         -0.221
_refine_diff_density_rms         0.039
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.035
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     182
_refine_ls_number_reflns         2631
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.035
_refine_ls_R_factor_all          0.0405
_refine_ls_R_factor_gt           0.0386
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0494P)²+0.2799P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0989
_refine_ls_wR_factor_ref         0.1006
_reflns_number_gt                2470
_reflns_number_total             2631
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo802706d_si_002.cif
_cod_data_source_block           compound_7
_cod_database_code               4024412
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
N1 N 0.67846(11) 0.59982(10) 0.83903(10) 0.0203(2) Uani 1 1 d . . .
N2 N 0.84485(17) 0.66689(15) 0.54660(15) 0.0480(4) Uani 1 1 d . . .
C1 C 0.89025(13) 0.67607(13) 1.06033(13) 0.0216(3) Uani 1 1 d . . .
C2 C 0.90699(14) 0.70405(13) 1.21643(13) 0.0231(3) Uani 1 1 d . . .
H2 H 0.8501 0.6430 1.2489 0.028 Uiso 1 1 calc R . .
C3 C 1.00805(14) 0.82251(14) 1.32461(14) 0.0252(3) Uani 1 1 d . . .
H3 H 1.0181 0.8404 1.4287 0.030 Uiso 1 1 calc R . .
C4 C 1.09360(14) 0.91365(14) 1.27716(14) 0.0265(3) Uani 1 1 d . . .
H4 H 1.1611 0.9929 1.3491 0.032 Uiso 1 1 calc R . .
C5 C 1.07802(14) 0.88597(14) 1.12125(15) 0.0274(3) Uani 1 1 d . . .
H5 H 1.1357 0.9466 1.0889 0.033 Uiso 1 1 calc R . .
C6 C 0.97677(14) 0.76829(14) 1.01368(14) 0.0250(3) Uani 1 1 d . . .
H6 H 0.9666 0.7509 0.9097 0.030 Uiso 1 1 calc R . .
C7 C 0.78167(14) 0.54707(13) 0.94177(13) 0.0225(3) Uani 1 1 d . . .
H7B H 0.8385 0.4702 0.8815 0.027 Uiso 1 1 calc R . .
H7A H 0.7234 0.5012 0.9935 0.027 Uiso 1 1 calc R . .
C8 C 0.53660(15) 0.33737(14) 0.70231(14) 0.0295(3) Uani 1 1 d . . .
H8A H 0.6133 0.2870 0.7429 0.044 Uiso 1 1 calc R . .
H8B H 0.4862 0.2701 0.6018 0.044 Uiso 1 1 calc R . .
H8C H 0.4646 0.3659 0.7690 0.044 Uiso 1 1 calc R . .
C9 C 0.60943(14) 0.47919(13) 0.69158(13) 0.0227(3) Uani 1 1 d . . .
H9 H 0.5294 0.5222 0.6413 0.027 Uiso 1 1 calc R . .
C10 C 0.72655(15) 0.43468(14) 0.58690(14) 0.0258(3) Uani 1 1 d . . .
H10A H 0.8060 0.3885 0.6318 0.031 Uiso 1 1 calc R . .
H10B H 0.6782 0.3599 0.4878 0.031 Uiso 1 1 calc R . .
C11 C 0.79400(16) 0.56504(15) 0.56442(14) 0.0309(3) Uani 1 1 d . . .
C12 C 0.56584(14) 0.68650(13) 0.91936(13) 0.0231(3) Uani 1 1 d . . .
H12A H 0.6159 0.7535 1.0217 0.028 Uiso 1 1 calc R . .
H12B H 0.4925 0.6167 0.9305 0.028 Uiso 1 1 calc R . .
C13 C 0.48339(14) 0.77991(13) 0.83836(13) 0.0230(3) Uani 1 1 d . . .
C14 C 0.56054(14) 0.85806(13) 0.77003(14) 0.0261(3) Uani 1 1 d . . .
H14 H 0.6628 0.8484 0.7693 0.031 Uiso 1 1 calc R . .
C15 C 0.48608(16) 0.95039(14) 0.70287(15) 0.0309(3) Uani 1 1 d . . .
H15 H 0.5388 1.0021 0.6576 0.037 Uiso 1 1 calc R . .
C16 C 0.33355(17) 0.96583(14) 0.70308(15) 0.0336(3) Uani 1 1 d . . .
H16 H 0.2841 1.0284 0.6589 0.040 Uiso 1 1 calc R . .
C17 C 0.25550(16) 0.88765(16) 0.76929(15) 0.0353(3) Uani 1 1 d . . .
H17 H 0.1531 0.8971 0.7692 0.042 Uiso 1 1 calc R . .
C18 C 0.33003(15) 0.79484(15) 0.83608(14) 0.0302(3) Uani 1 1 d . . .
H18 H 0.2766 0.7420 0.8798 0.036 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 0.0181 0.0091 '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 0.0311 0.0180 '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 C7 110.55(9) . . ?
C12 N1 C9 112.49(9) . . ?
C7 N1 C9 114.01(9) . . ?
C2 C1 C6 118.88(11) . . ?
C2 C1 C7 121.18(11) . . ?
C6 C1 C7 119.94(10) . . ?
C1 C2 C3 120.72(11) . . ?
C1 C2 H2 119.6 . . ?
C3 C2 H2 119.6 . . ?
C4 C3 C2 119.99(11) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C4 C5 119.63(11) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
C6 C5 C4 120.29(12) . . ?
C6 C5 H5 119.9 . . ?
C4 C5 H5 119.9 . . ?
C5 C6 C1 120.48(11) . . ?
C5 C6 H6 119.8 . . ?
C1 C6 H6 119.8 . . ?
N1 C7 C1 111.39(9) . . ?
N1 C7 H7B 109.4 . . ?
C1 C7 H7B 109.4 . . ?
N1 C7 H7A 109.4 . . ?
C1 C7 H7A 109.4 . . ?
H7B C7 H7A 108.0 . . ?
C9 C8 H8A 109.5 . . ?
C9 C8 H8B 109.5 . . ?
H8A C8 H8B 109.5 . . ?
C9 C8 H8C 109.5 . . ?
H8A C8 H8C 109.5 . . ?
H8B C8 H8C 109.5 . . ?
N1 C9 C8 115.73(9) . . ?
N1 C9 C10 109.81(10) . . ?
C8 C9 C10 109.77(10) . . ?
N1 C9 H9 107.0 . . ?
C8 C9 H9 107.0 . . ?
C10 C9 H9 107.0 . . ?
C11 C10 C9 112.40(10) . . ?
C11 C10 H10A 109.1 . . ?
C9 C10 H10A 109.1 . . ?
C11 C10 H10B 109.1 . . ?
C9 C10 H10B 109.1 . . ?
H10A C10 H10B 107.9 . . ?
N2 C11 C10 179.22(16) . . ?
N1 C12 C13 113.70(9) . . ?
N1 C12 H12A 108.8 . . ?
C13 C12 H12A 108.8 . . ?
N1 C12 H12B 108.8 . . ?
C13 C12 H12B 108.8 . . ?
H12A C12 H12B 107.7 . . ?
C18 C13 C14 118.54(11) . . ?
C18 C13 C12 120.70(11) . . ?
C14 C13 C12 120.71(11) . . ?
C15 C14 C13 120.57(12) . . ?
C15 C14 H14 119.7 . . ?
C13 C14 H14 119.7 . . ?
C16 C15 C14 120.33(13) . . ?
C16 C15 H15 119.8 . . ?
C14 C15 H15 119.8 . . ?
C17 C16 C15 119.59(12) . . ?
C17 C16 H16 120.2 . . ?
C15 C16 H16 120.2 . . ?
C16 C17 C18 120.04(13) . . ?
C16 C17 H17 120.0 . . ?
C18 C17 H17 120.0 . . ?
C13 C18 C17 120.92(13) . . ?
C13 C18 H18 119.5 . . ?
C17 C18 H18 119.5 . . ?
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 C12 1.4650(15) . ?
N1 C7 1.4673(14) . ?
N1 C9 1.4711(15) . ?
N2 C11 1.1403(18) . ?
C1 C2 1.3913(17) . ?
C1 C6 1.3925(17) . ?
C1 C7 1.5123(16) . ?
C2 C3 1.3926(17) . ?
C2 H2 0.9300 . ?
C3 C4 1.3847(18) . ?
C3 H3 0.9300 . ?
C4 C5 1.3909(18) . ?
C4 H4 0.9300 . ?
C5 C6 1.3877(18) . ?
C5 H5 0.9300 . ?
C6 H6 0.9300 . ?
C7 H7B 0.9700 . ?
C7 H7A 0.9700 . ?
C8 C9 1.5289(16) . ?
C8 H8A 0.9600 . ?
C8 H8B 0.9600 . ?
C8 H8C 0.9600 . ?
C9 C10 1.5364(17) . ?
C9 H9 0.9800 . ?
C10 C11 1.4666(18) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C12 C13 1.5110(16) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C18 1.3914(19) . ?
C13 C14 1.3919(18) . ?
C14 C15 1.3897(18) . ?
C14 H14 0.9300 . ?
C15 C16 1.388(2) . ?
C15 H15 0.9300 . ?
C16 C17 1.382(2) . ?
C16 H16 0.9300 . ?
C17 C18 1.3916(19) . ?
C17 H17 0.9300 . ?
C18 H18 0.9300 . ?
