#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:08:28 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201955 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/00/84/2008473.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_2008473
loop_
_publ_author_name
'Brigas, Amadeu F.'
'Clegg, William'
'Johnstone, Robert A.W.'
'Mendonca, Ricardo F.'
_publ_section_title
;
 5-Benzyloxy-1-phenyltetrazole: catalytic transfer hydrogenolysis of
 benzyl ethers
;
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              778
_journal_page_last               781
_journal_paper_doi               10.1107/S0108270199000141
_journal_volume                  55
_journal_year                    1999
_chemical_formula_sum            'C14 H12 N4 O'
_chemical_formula_weight         252.28
_chemical_name_systematic        5-benzyloxy-1[H]-phenyltetrazole
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_audit_creation_method           SHELXL-97
_cell_angle_alpha                90.00
_cell_angle_beta                 98.008(4)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.5461(15)
_cell_length_b                   6.2510(10)
_cell_length_c                   20.773(3)
_cell_measurement_reflns_used    2880
_cell_measurement_temperature    160(2)
_cell_measurement_theta_max      28.12
_cell_measurement_theta_min      2.15
_cell_volume                     1227.5(3)
_computing_cell_refinement       'local programs'
_computing_data_collection       'SMART (Bruker, 1995)'
_computing_data_reduction        'SAINT (Bruker, 1995)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material  'SHELXTL and local programs'
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Sheldrick, 1994)'
_diffrn_ambient_temperature      160(2)
_diffrn_detector_area_resol_mean 8.192
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.913
_diffrn_measurement_device_type  'Bruker AXS SMART CCD diffractometer'
_diffrn_measurement_method       'ω rotation with narrow frames'
_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  0.0468
_diffrn_reflns_av_sigmaI/netI    0.0734
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            7286
_diffrn_reflns_theta_full        26.00
_diffrn_reflns_theta_max         28.71
_diffrn_reflns_theta_min         1.98
_diffrn_standards_decay_%        0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.365
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       plate
_exptl_crystal_F_000             528
_exptl_crystal_size_max          0.50
_exptl_crystal_size_mid          0.45
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.212
_refine_diff_density_min         -0.212
_refine_ls_extinction_coef       0.0089(13)
_refine_ls_extinction_method     'SHELXTL (Sheldrick, 1994)'
_refine_ls_goodness_of_fit_ref   0.910
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         2911
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.910
_refine_ls_R_factor_all          0.0902
_refine_ls_R_factor_gt           0.0397
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w = 1/[σ²(Fo²)+(0.0403P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_ref         0.0896
_reflns_number_gt                1713
_reflns_number_total             2911
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            ln1073.cif
_cod_data_source_block           liv4
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2008473
_cod_database_fobs_code          2008473
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_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
_atom_site_type_symbol
O .35875(9) .45913(15) .32441(4) .0245(3) Uani d . 1 . . O
N1 .56377(13) .46454(18) .27091(6) .0246(3) Uani d . 1 . . N
N2 .57495(13) .47024(18) .20545(6) .0265(3) Uani d . 1 . . N
N3 .45237(13) .47389(18) .17029(6) .0250(3) Uani d . 1 . . N
N4 .35491(12) .46934(17) .21262(6) .0207(3) Uani d . 1 . . N
C1 .42659(15) .4640(2) .27290(7) .0197(3) Uani d . 1 . . C
C2 .45167(15) .4612(2) .38695(7) .0268(4) Uani d . 1 . . C
H2A .4982 .6023 .3943 .032 Uiso calc R 1 . . H
H2B .5258 .3502 .3875 .032 Uiso calc R 1 . . H
C3 .36051(15) .4168(2) .43856(7) .0221(3) Uani d . 1 . . C
C4 .27581(16) .5751(2) .45909(7) .0304(4) Uani d . 1 . . C
H4 .2759 .7140 .4405 .036 Uiso calc R 1 . . H
C5 .19067(17) .5330(3) .50653(8) .0389(4) Uani d . 1 . . C
H5 .1320 .6421 .5201 .047 Uiso calc R 1 . . H
C6 .19152(17) .3311(3) .53404(8) .0429(5) Uani d . 1 . . C
H6 .1334 .3015 .5665 .051 Uiso calc R 1 . . H
C7 .27643(18) .1735(3) .51433(8) .0392(4) Uani d . 1 . . C
H7 .2775 .0354 .5335 .047 Uiso calc R 1 . . H
C8 .36034(16) .2154(2) .46670(7) .0295(4) Uani d . 1 . . C
H8 .4184 .1055 .4531 .035 Uiso calc R 1 . . H
C9 .20563(15) .4752(2) .19176(7) .0211(3) Uani d . 1 . . C
C10 .14706(15) .6521(2) .15845(7) .0273(4) Uani d . 1 . . C
H10 .2050 .7679 .1487 .033 Uiso calc R 1 . . H
C11 .00234(16) .6575(3) .13955(8) .0333(4) Uani d . 1 . . C
H11 -.0396 .7774 .1163 .040 Uiso calc R 1 . . H
C12 -.08177(16) .4887(3) .15445(8) .0331(4) Uani d . 1 . . C
H12 -.1813 .4940 .1419 .040 Uiso calc R 1 . . H
C13 -.02092(16) .3128(3) .18752(8) .0334(4) Uani d . 1 . . C
H13 -.0788 .1972 .1975 .040 Uiso calc R 1 . . H
C14 .12393(15) .3042(2) .20627(7) .0274(4) Uani d . 1 . . C
H14 .1663 .1829 .2287 .033 Uiso calc R 1 . . H
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_publ_flag
C1 O C2 114.28(10) yes
C1 N1 N2 104.19(12) no
N3 N2 N1 111.71(11) no
N2 N3 N4 106.28(11) no
C1 N4 N3 107.26(11) no
C1 N4 C9 129.82(11) no
N3 N4 C9 122.90(11) no
N1 C1 O 128.72(13) yes
N1 C1 N4 110.55(12) yes
O C1 N4 120.73(12) yes
O C2 C3 106.99(11) yes
C4 C3 C8 118.96(14) no
C4 C3 C2 120.76(13) no
C8 C3 C2 120.28(13) no
C3 C4 C5 120.61(14) no
C6 C5 C4 119.72(15) no
C7 C6 C5 120.01(15) no
C6 C7 C8 120.16(15) no
C7 C8 C3 120.54(15) no
C14 C9 C10 121.85(14) no
C14 C9 N4 118.89(13) no
C10 C9 N4 119.25(13) no
C9 C10 C11 118.71(14) no
C10 C11 C12 120.32(15) no
C13 C12 C11 120.01(14) no
C12 C13 C14 120.38(14) no
C9 C14 C13 118.72(14) no
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
O C1 . 1.3261(15) yes
O C2 . 1.4676(16) yes
N1 C1 . 1.3159(17) yes
N1 N2 . 1.3791(17) yes
N2 N3 . 1.2904(17) yes
N3 N4 . 1.3665(15) yes
N4 C1 . 1.3412(18) yes
N4 C9 . 1.4310(17) no
C2 C3 . 1.498(2) yes
C3 C4 . 1.382(2) no
C3 C8 . 1.3882(19) no
C4 C5 . 1.387(2) no
C5 C6 . 1.385(2) no
C6 C7 . 1.374(2) no
C7 C8 . 1.382(2) no
C9 C14 . 1.3810(19) no
C9 C10 . 1.381(2) no
C10 C11 . 1.383(2) no
C11 C12 . 1.387(2) no
C12 C13 . 1.381(2) no
C13 C14 . 1.384(2) no
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
_geom_torsion_publ_flag
C1 N1 N2 N3 0.27(15) no
N1 N2 N3 N4 -0.35(14) no
N2 N3 N4 C1 0.29(14) no
N2 N3 N4 C9 178.90(12) no
N2 N1 C1 O 179.90(12) no
N2 N1 C1 N4 -0.07(14) no
C2 O C1 N1 2.04(19) yes
C2 O C1 N4 -177.99(12) yes
N3 N4 C1 N1 -0.13(15) no
C9 N4 C1 N1 -178.61(12) no
N3 N4 C1 O 179.89(11) no
C9 N4 C1 O 1.4(2) no
C1 O C2 C3 -170.36(11) yes
O C2 C3 C4 -77.53(16) yes
O C2 C3 C8 102.69(15) yes
C8 C3 C4 C5 -0.7(2) no
C2 C3 C4 C5 179.49(14) no
C3 C4 C5 C6 0.6(2) no
C4 C5 C6 C7 0.0(2) no
C5 C6 C7 C8 -0.5(2) no
C6 C7 C8 C3 0.4(2) no
C4 C3 C8 C7 0.2(2) no
C2 C3 C8 C7 -179.98(14) no
C1 N4 C9 C14 -63.31(19) yes
N3 N4 C9 C14 118.43(14) no
C1 N4 C9 C10 115.93(16) no
N3 N4 C9 C10 -62.34(17) yes
C14 C9 C10 C11 0.3(2) no
N4 C9 C10 C11 -178.88(13) no
C9 C10 C11 C12 0.6(2) no
C10 C11 C12 C13 -0.9(2) no
C11 C12 C13 C14 0.3(2) no
C10 C9 C14 C13 -0.9(2) no
N4 C9 C14 C13 178.31(13) no
C12 C13 C14 C9 0.6(2) no
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 4259150
