#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/44/4024411.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_4024411
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         'C16 H20 N, Br'
_chemical_formula_sum            'C16 H20 Br N'
_chemical_formula_weight         306.24
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 91.4850(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   12.9824(3)
_cell_length_b                   10.2376(2)
_cell_length_c                   10.7952(2)
_cell_measurement_reflns_used    9966
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      69.2364
_cell_measurement_theta_min      3.4053
_cell_volume                     1434.29(5)
_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 0.953
_diffrn_measured_fraction_theta_max 0.953
_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  0.0206
_diffrn_reflns_av_sigmaI/netI    0.0146
_diffrn_reflns_limit_h_max       15
_diffrn_reflns_limit_h_min       -15
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            17289
_diffrn_reflns_theta_full        69.70
_diffrn_reflns_theta_max         69.70
_diffrn_reflns_theta_min         3.41
_diffrn_source                   'fine-focus sealed tube'
_diffrn_source_type              'Siemens KFFCU2K-90'
_exptl_absorpt_coefficient_mu    3.744
_exptl_absorpt_correction_T_max  0.68
_exptl_absorpt_correction_T_min  0.31
_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    1.418
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       parallelepiped
_exptl_crystal_F_000             632
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.10
_refine_diff_density_max         0.323
_refine_diff_density_min         -0.198
_refine_diff_density_rms         0.048
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.079
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     165
_refine_ls_number_reflns         2579
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.079
_refine_ls_R_factor_all          0.0215
_refine_ls_R_factor_gt           0.0209
_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)+(0.0267P)²+0.9166P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0534
_refine_ls_wR_factor_ref         0.0538
_reflns_number_gt                2521
_reflns_number_total             2579
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo802706d_si_001.cif
_cod_data_source_block           compound_3
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               4024411
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, 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
Br1 Br 0.712740(12) 0.051414(15) 0.434127(14) 0.02031(8) Uani 1 1 d . . .
N1 N 0.80445(10) 0.40762(13) 0.57019(11) 0.0152(3) Uani 1 1 d . . .
C1 C 0.54844(13) 0.64259(19) 0.27905(19) 0.0333(4) Uani 1 1 d . . .
H1 H 0.5184 0.6959 0.2184 0.040 Uiso 1 1 calc R . .
C2 C 0.56813(13) 0.69171(18) 0.39658(19) 0.0320(4) Uani 1 1 d . . .
H2 H 0.5519 0.7780 0.4146 0.038 Uiso 1 1 calc R . .
C3 C 0.61231(12) 0.61192(17) 0.48797(17) 0.0255(4) Uani 1 1 d . . .
H3 H 0.6240 0.6444 0.5676 0.031 Uiso 1 1 calc R . .
C4 C 0.63912(11) 0.48335(16) 0.46041(15) 0.0190(3) Uani 1 1 d . . .
C5 C 0.68661(11) 0.39496(15) 0.55795(14) 0.0180(3) Uani 1 1 d . . .
H5A H 0.6693 0.3051 0.5378 0.022 Uiso 1 1 calc R . .
H5B H 0.6569 0.4151 0.6372 0.022 Uiso 1 1 calc R . .
C6 C 0.84010(12) 0.30396(15) 0.66432(14) 0.0170(3) Uani 1 1 d . . .
H6A H 0.8007 0.3136 0.7389 0.020 Uiso 1 1 calc R . .
H6B H 0.8254 0.2181 0.6303 0.020 Uiso 1 1 calc R . .
C7 C 0.95321(12) 0.31219(14) 0.69826(14) 0.0170(3) Uani 1 1 d . . .
C8 C 1.02636(13) 0.24376(15) 0.63108(15) 0.0205(3) Uani 1 1 d . . .
H8 H 1.0049 0.1905 0.5655 0.025 Uiso 1 1 calc R . .
C9 C 1.13067(13) 0.25435(16) 0.66108(16) 0.0241(4) Uani 1 1 d . . .
H9 H 1.1787 0.2092 0.6151 0.029 Uiso 1 1 calc R . .
C10 C 1.16312(13) 0.33238(16) 0.75969(16) 0.0244(4) Uani 1 1 d . . .
H10 H 1.2330 0.3401 0.7794 0.029 Uiso 1 1 calc R . .
C11 C 0.61902(13) 0.43524(17) 0.34158(17) 0.0231(4) Uani 1 1 d . . .
H11 H 0.6363 0.3495 0.3227 0.028 Uiso 1 1 calc R . .
C12 C 0.57328(13) 0.5142(2) 0.25091(18) 0.0298(4) Uani 1 1 d . . .
H12 H 0.5594 0.4813 0.1719 0.036 Uiso 1 1 calc R . .
C13 C 1.09118(13) 0.39920(16) 0.82920(15) 0.0225(3) Uani 1 1 d . . .
H13 H 1.1129 0.4506 0.8959 0.027 Uiso 1 1 calc R . .
C14 C 0.98696(12) 0.38897(15) 0.79868(14) 0.0194(3) Uani 1 1 d . . .
H14 H 0.9391 0.4336 0.8454 0.023 Uiso 1 1 calc R . .
C15 C 0.85302(12) 0.38317(15) 0.44836(14) 0.0181(3) Uani 1 1 d . . .
H15A H 0.8301 0.4482 0.3898 0.027 Uiso 1 1 calc R . .
H15B H 0.8335 0.2981 0.4186 0.027 Uiso 1 1 calc R . .
H15C H 0.9266 0.3875 0.4585 0.027 Uiso 1 1 calc R . .
C16 C 0.83147(13) 0.54101(14) 0.61675(16) 0.0192(3) Uani 1 1 d . . .
H16A H 0.9049 0.5483 0.6268 0.029 Uiso 1 1 calc R . .
H16B H 0.8000 0.5552 0.6951 0.029 Uiso 1 1 calc R . .
H16C H 0.8069 0.6052 0.5583 0.029 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'
Br Br -0.6763 1.2805 '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
C16 N1 C15 110.40(12) . . ?
C16 N1 C6 110.22(11) . . ?
C15 N1 C6 109.91(11) . . ?
C16 N1 C5 109.29(12) . . ?
C15 N1 C5 110.60(11) . . ?
C6 N1 C5 106.34(11) . . ?
C2 C1 C12 120.43(17) . . ?
C2 C1 H1 119.8 . . ?
C12 C1 H1 119.8 . . ?
C1 C2 C3 119.98(17) . . ?
C1 C2 H2 120.0 . . ?
C3 C2 H2 120.0 . . ?
C2 C3 C4 120.16(17) . . ?
C2 C3 H3 119.9 . . ?
C4 C3 H3 119.9 . . ?
C11 C4 C3 119.23(16) . . ?
C11 C4 C5 119.63(15) . . ?
C3 C4 C5 121.12(15) . . ?
C4 C5 N1 113.41(12) . . ?
C4 C5 H5A 108.9 . . ?
N1 C5 H5A 108.9 . . ?
C4 C5 H5B 108.9 . . ?
N1 C5 H5B 108.9 . . ?
H5A C5 H5B 107.7 . . ?
C7 C6 N1 113.47(12) . . ?
C7 C6 H6A 108.9 . . ?
N1 C6 H6A 108.9 . . ?
C7 C6 H6B 108.9 . . ?
N1 C6 H6B 108.9 . . ?
H6A C6 H6B 107.7 . . ?
C8 C7 C14 118.67(15) . . ?
C8 C7 C6 121.11(14) . . ?
C14 C7 C6 120.21(14) . . ?
C9 C8 C7 120.76(16) . . ?
C9 C8 H8 119.6 . . ?
C7 C8 H8 119.6 . . ?
C10 C9 C8 119.92(15) . . ?
C10 C9 H9 120.0 . . ?
C8 C9 H9 120.0 . . ?
C9 C10 C13 120.11(15) . . ?
C9 C10 H10 119.9 . . ?
C13 C10 H10 119.9 . . ?
C12 C11 C4 120.60(17) . . ?
C12 C11 H11 119.7 . . ?
C4 C11 H11 119.7 . . ?
C1 C12 C11 119.58(18) . . ?
C1 C12 H12 120.2 . . ?
C11 C12 H12 120.2 . . ?
C14 C13 C10 119.88(16) . . ?
C14 C13 H13 120.1 . . ?
C10 C13 H13 120.1 . . ?
C13 C14 C7 120.64(15) . . ?
C13 C14 H14 119.7 . . ?
C7 C14 H14 119.7 . . ?
N1 C15 H15A 109.5 . . ?
N1 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
N1 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 109.5 . . ?
N1 C16 H16A 109.5 . . ?
N1 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
N1 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 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 C16 1.4939(19) . ?
N1 C15 1.4943(18) . ?
N1 C6 1.5325(19) . ?
N1 C5 1.5376(19) . ?
C1 C2 1.383(3) . ?
C1 C12 1.388(3) . ?
C1 H1 0.9300 . ?
C2 C3 1.393(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.396(2) . ?
C3 H3 0.9300 . ?
C4 C11 1.392(2) . ?
C4 C5 1.508(2) . ?
C5 H5A 0.9700 . ?
C5 H5B 0.9700 . ?
C6 C7 1.506(2) . ?
C6 H6A 0.9700 . ?
C6 H6B 0.9700 . ?
C7 C8 1.398(2) . ?
C7 C14 1.400(2) . ?
C8 C9 1.388(2) . ?
C8 H8 0.9300 . ?
C9 C10 1.388(3) . ?
C9 H9 0.9300 . ?
C10 C13 1.393(2) . ?
C10 H10 0.9300 . ?
C11 C12 1.391(3) . ?
C11 H11 0.9300 . ?
C12 H12 0.9300 . ?
C13 C14 1.388(2) . ?
C13 H13 0.9300 . ?
C14 H14 0.9300 . ?
C15 H15A 0.9600 . ?
C15 H15B 0.9600 . ?
C15 H15C 0.9600 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 9407066
