#------------------------------------------------------------------------------
#$Date: 2016-02-18 16:37:37 +0100 (jue 18 de feb de 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/52/1515255.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_1515255
loop_
_publ_author_name
'Sonobe, Toshiaki'
'Oisaki, Kounosuke'
'Kanai, Motomu'
_publ_section_title
;
 Catalytic aerobic production of imines en route to mild, green, and
 concise derivatizations of amines
;
_journal_issue                   11
_journal_name_full               'Chemical Science'
_journal_page_first              3249
_journal_paper_doi               10.1039/c2sc20699d
_journal_volume                  3
_journal_year                    2012
_chemical_formula_sum            'C8 H12 N O2'
_chemical_formula_weight         154.19
_chemical_name_systematic
;
?
;
_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'
_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                 105.8626(17)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   7.3754(2)
_cell_length_b                   11.0558(3)
_cell_length_c                   9.6355(3)
_cell_measurement_reflns_used    5766
_cell_measurement_temperature    111(2)
_cell_measurement_theta_max      68.2
_cell_measurement_theta_min      4.8
_cell_volume                     755.77(4)
_computing_cell_refinement       PROCESS-AUTO
_computing_data_collection       PROCESS-AUTO
_computing_molecular_graphics
'Yadokari-XG 2009 (Wakita, Nemoto et al., 2009)'
_computing_publication_material
'Yadokari-XG 2009 (Wakita, Nemoto et al., 2009)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      111(2)
_diffrn_detector_area_resol_mean 10.00
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Rigaku RAXIS-RAPID'
_diffrn_measurement_method       ω
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54187
_diffrn_reflns_av_R_equivalents  0.0380
_diffrn_reflns_av_sigmaI/netI    0.0291
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       11
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            8282
_diffrn_reflns_theta_full        68.23
_diffrn_reflns_theta_max         68.23
_diffrn_reflns_theta_min         6.23
_exptl_absorpt_coefficient_mu    0.798
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.8674
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
Higashi, T. (1995). Program for Absorption Correction.
Rigaku Corporation, Tokyo, Japan.
;
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.355
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             332
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.561
_refine_diff_density_min         -0.212
_refine_diff_density_rms         0.054
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.114
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     100
_refine_ls_number_reflns         1379
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.114
_refine_ls_R_factor_all          0.0577
_refine_ls_R_factor_gt           0.0414
_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)+(0.0409P)²+0.5745P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0964
_refine_ls_wR_factor_ref         0.1173
_reflns_number_gt                1075
_reflns_number_total             1379
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            c2sc20699d.txt
_cod_data_source_block           ydkr
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1515255
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
O2 O 0.89436(18) 0.42188(12) 0.54281(13) 0.0236(3) Uani 1 1 d .
N2 N 0.8666(2) 0.44294(14) 0.40718(15) 0.0199(4) Uani 1 1 d .
O1 O 0.4448(2) 0.27470(14) 0.11420(16) 0.0404(4) Uani 1 1 d .
C2 C 0.7356(3) 0.57576(18) 0.2022(2) 0.0236(4) Uani 1 1 d .
H1 H 0.8337 0.6385 0.2350 0.028 Uiso 1 1 calc R
H2 H 0.6186 0.6166 0.1472 0.028 Uiso 1 1 calc R
C3 C 0.6997(2) 0.51402(17) 0.33398(19) 0.0211(4) Uani 1 1 d .
H3 H 0.6785 0.5776 0.4017 0.025 Uiso 1 1 calc R
C4 C 0.5291(3) 0.42754(19) 0.2973(2) 0.0268(5) Uani 1 1 d .
H4 H 0.5004 0.4027 0.3877 0.032 Uiso 1 1 calc R
H5 H 0.4178 0.4711 0.2373 0.032 Uiso 1 1 calc R
C5 C 0.9173(3) 0.34799(18) 0.31760(19) 0.0231(4) Uani 1 1 d .
H6 H 1.0331 0.3055 0.3754 0.028 Uiso 1 1 calc R
C1 C 0.5632(3) 0.31624(18) 0.2177(2) 0.0269(5) Uani 1 1 d .
C6 C 0.7990(3) 0.48736(18) 0.1022(2) 0.0251(5) Uani 1 1 d .
H7 H 0.6910 0.4362 0.0516 0.030 Uiso 1 1 calc R
H8 H 0.8410 0.5335 0.0285 0.030 Uiso 1 1 calc R
C7 C 0.7530(3) 0.25632(19) 0.2772(2) 0.0279(5) Uani 1 1 d .
H9 H 0.7752 0.1993 0.2044 0.033 Uiso 1 1 calc R
H10 H 0.7510 0.2090 0.3640 0.033 Uiso 1 1 calc R
C8 C 0.9597(3) 0.40683(19) 0.1864(2) 0.0254(5) Uani 1 1 d .
H11 H 1.0759 0.4560 0.2189 0.030 Uiso 1 1 calc R
H12 H 0.9833 0.3427 0.1217 0.030 Uiso 1 1 calc R
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O2 0.0287(7) 0.0251(8) 0.0173(6) 0.0022(5) 0.0068(5) -0.0017(6)
N2 0.0209(8) 0.0189(8) 0.0188(8) 0.0005(6) 0.0036(6) 0.0006(6)
O1 0.0451(10) 0.0360(9) 0.0339(8) 0.0048(7) 0.0003(7) -0.0153(7)
C2 0.0254(10) 0.0194(10) 0.0239(9) 0.0022(8) 0.0032(8) 0.0005(8)
C3 0.0203(9) 0.0207(10) 0.0229(9) 0.0006(8) 0.0069(8) 0.0026(7)
C4 0.0208(10) 0.0329(12) 0.0271(10) 0.0037(9) 0.0072(8) -0.0023(8)
C5 0.0238(10) 0.0214(10) 0.0230(9) -0.0032(8) 0.0046(8) 0.0036(8)
C1 0.0312(11) 0.0252(11) 0.0227(10) 0.0044(8) 0.0048(8) -0.0107(9)
C6 0.0268(10) 0.0269(11) 0.0224(10) -0.0004(8) 0.0082(8) -0.0038(8)
C7 0.0354(11) 0.0209(11) 0.0267(10) 0.0000(8) 0.0074(9) -0.0021(8)
C8 0.0257(10) 0.0293(11) 0.0230(9) -0.0035(8) 0.0097(8) 0.0008(8)
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'
O O 0.0492 0.0322 '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
O2 N2 C3 117.67(14)
O2 N2 C5 118.11(14)
C3 N2 C5 114.48(14)
C3 C2 C6 112.95(16)
C3 C2 H1 109.0
C6 C2 H1 109.0
C3 C2 H2 109.0
C6 C2 H2 109.0
H1 C2 H2 107.8
N2 C3 C2 109.00(14)
N2 C3 C4 107.61(15)
C2 C3 C4 113.72(15)
N2 C3 H3 108.8
C2 C3 H3 108.8
C4 C3 H3 108.8
C1 C4 C3 112.57(15)
C1 C4 H4 109.1
C3 C4 H4 109.1
C1 C4 H5 109.1
C3 C4 H5 109.1
H4 C4 H5 107.8
N2 C5 C8 108.91(15)
N2 C5 C7 107.94(15)
C8 C5 C7 113.25(15)
N2 C5 H6 108.9
C8 C5 H6 108.9
C7 C5 H6 108.9
O1 C1 C4 122.75(19)
O1 C1 C7 121.7(2)
C4 C1 C7 115.52(16)
C8 C6 C2 111.32(15)
C8 C6 H7 109.4
C2 C6 H7 109.4
C8 C6 H8 109.4
C2 C6 H8 109.4
H7 C6 H8 108.0
C1 C7 C5 112.88(16)
C1 C7 H9 109.0
C5 C7 H9 109.0
C1 C7 H10 109.0
C5 C7 H10 109.0
H9 C7 H10 107.8
C6 C8 C5 112.53(15)
C6 C8 H11 109.1
C5 C8 H11 109.1
C6 C8 H12 109.1
C5 C8 H12 109.1
H11 C8 H12 107.8
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
O2 N2 1.2875(18)
N2 C3 1.468(2)
N2 C5 1.471(2)
O1 C1 1.222(2)
C2 C3 1.527(2)
C2 C6 1.533(3)
C2 H1 0.9900
C2 H2 0.9900
C3 C4 1.542(3)
C3 H3 1.0000
C4 C1 1.507(3)
C4 H4 0.9900
C4 H5 0.9900
C5 C8 1.528(3)
C5 C7 1.546(3)
C5 H6 1.0000
C1 C7 1.513(3)
C6 C8 1.527(3)
C6 H7 0.9900
C6 H8 0.9900
C7 H9 0.9900
C7 H10 0.9900
C8 H11 0.9900
C8 H12 0.9900
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
O2 N2 C3 C2 154.84(15)
C5 N2 C3 C2 -59.74(19)
O2 N2 C3 C4 -81.40(18)
C5 N2 C3 C4 64.02(18)
C6 C2 C3 N2 52.8(2)
C6 C2 C3 C4 -67.2(2)
N2 C3 C4 C1 -51.9(2)
C2 C3 C4 C1 69.0(2)
O2 N2 C5 C8 -154.33(15)
C3 N2 C5 C8 60.41(19)
O2 N2 C5 C7 82.34(18)
C3 N2 C5 C7 -62.92(19)
C3 C4 C1 O1 -137.09(19)
C3 C4 C1 C7 44.6(2)
C3 C2 C6 C8 -49.4(2)
O1 C1 C7 C5 138.15(19)
C4 C1 C7 C5 -43.5(2)
N2 C5 C7 C1 49.7(2)
C8 C5 C7 C1 -71.0(2)
C2 C6 C8 C5 49.9(2)
N2 C5 C8 C6 -54.0(2)
C7 C5 C8 C6 66.1(2)
