#------------------------------------------------------------------------------
#$Date: 2016-02-18 17:37:37 +0200 (Thu, 18 Feb 2016) $
#$Revision: 176729 $
#$URL: svn://www.crystallography.net/cod/cif/1/51/65/1516518.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_1516518
loop_
_publ_author_name
'Zhang, Zhi-Jing'
'Quan, Xue-Jing'
'Ren, Zhi-Hui'
'Wang, Yao-Yu'
'Guan, Zheng-Hui'
_publ_section_title
;
 A Facile BPO-Mediated ortho-Hydroxylation and Benzoylation of N-Alkyl
 Anilines for Synthesis of 2-Benzamidophenols.
;
_journal_issue                   12
_journal_name_full               'Organic letters'
_journal_page_first              3292
_journal_page_last               3295
_journal_paper_doi               10.1021/ol501293c
_journal_volume                  16
_journal_year                    2014
_chemical_formula_sum            'C14 H13 N O2'
_chemical_formula_weight         227.25
_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                 106.880(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   8.2260(13)
_cell_length_b                   11.7110(18)
_cell_length_c                   13.239(2)
_cell_measurement_reflns_used    1188
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      21.43
_cell_measurement_theta_min      2.37
_cell_volume                     1220.4(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and 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  0.0288
_diffrn_reflns_av_sigmaI/netI    0.0378
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            5938
_diffrn_reflns_theta_full        25.10
_diffrn_reflns_theta_max         25.10
_diffrn_reflns_theta_min         2.37
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  0.9793
_exptl_absorpt_correction_T_min  0.9700
_exptl_absorpt_correction_type   none
_exptl_crystal_density_diffrn    1.237
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             480
_exptl_crystal_size_max          0.37
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.25
_refine_diff_density_max         0.157
_refine_diff_density_min         -0.174
_refine_diff_density_rms         0.038
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     156
_refine_ls_number_reflns         2154
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.029
_refine_ls_R_factor_all          0.0675
_refine_ls_R_factor_gt           0.0473
_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)+(0.0646P)²+0.1625P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1185
_refine_ls_wR_factor_ref         0.1348
_reflns_number_gt                1523
_reflns_number_total             2154
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            ol501293c_si_002.cif
_cod_data_source_block           xb6748_0m
_cod_depositor_comments
;
The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to
/usr/data/users/saulius/crontab/automatic-downloads/rss-feeds/ACS/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 from 2011-04-26.

Automatic conversion script
Id: cif_fix_values 2281 2013-09-26 08:29:07Z andrius 

 Adding full bibliography for 1516517--1516518.cif.
;
_cod_original_sg_symbol_H-M      P2(1)/c
_cod_database_code               1516518
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
N1 N 1.07500(18) 0.59765(13) 0.22491(11) 0.0476(4) Uani 1 1 d .
O1 O 1.10084(16) 0.65542(12) 0.06835(10) 0.0593(4) Uani 1 1 d .
O2 O 1.0443(2) 0.72746(12) 0.38849(11) 0.0649(4) Uani 1 1 d .
H2 H 1.0421 0.7546 0.4452 0.097 Uiso 1 1 calc R
C1 C 0.7378(3) 0.7259(2) 0.13563(18) 0.0693(7) Uani 1 1 d .
H1 H 0.7955 0.7606 0.1991 0.083 Uiso 1 1 calc R
C2 C 0.5684(4) 0.7450(3) 0.0915(3) 0.1015(11) Uani 1 1 d .
H2A H 0.5113 0.7934 0.1255 0.122 Uiso 1 1 calc R
C3 C 0.4810(4) 0.6949(4) -0.0011(4) 0.1195(14) Uani 1 1 d .
H3 H 0.3653 0.7085 -0.0299 0.143 Uiso 1 1 calc R
C4 C 0.5652(4) 0.6241(3) -0.0514(3) 0.1046(10) Uani 1 1 d .
H4 H 0.5063 0.5892 -0.1145 0.126 Uiso 1 1 calc R
C5 C 0.7361(3) 0.6043(2) -0.00904(19) 0.0715(6) Uani 1 1 d .
H5 H 0.7931 0.5571 -0.0440 0.086 Uiso 1 1 calc R
C6 C 0.8230(2) 0.65450(16) 0.08509(15) 0.0484(5) Uani 1 1 d .
C7 C 1.0092(2) 0.63583(15) 0.12567(14) 0.0447(5) Uani 1 1 d .
C8 C 0.9691(2) 0.56080(16) 0.28801(14) 0.0454(5) Uani 1 1 d .
C9 C 0.8830(3) 0.45842(17) 0.26618(16) 0.0572(5) Uani 1 1 d .
H9 H 0.8955 0.4124 0.2117 0.069 Uiso 1 1 calc R
C10 C 0.7788(3) 0.42461(19) 0.32494(18) 0.0662(6) Uani 1 1 d .
H10 H 0.7208 0.3556 0.3104 0.079 Uiso 1 1 calc R
C11 C 0.7604(3) 0.49293(19) 0.40530(17) 0.0646(6) Uani 1 1 d .
H11 H 0.6881 0.4705 0.4442 0.077 Uiso 1 1 calc R
C12 C 0.8475(3) 0.59371(18) 0.42863(15) 0.0579(5) Uani 1 1 d .
H12 H 0.8348 0.6390 0.4835 0.069 Uiso 1 1 calc R
C13 C 0.9545(2) 0.62839(16) 0.37077(14) 0.0482(5) Uani 1 1 d .
C14 C 1.2589(2) 0.5842(2) 0.26893(17) 0.0676(6) Uani 1 1 d .
H14A H 1.2859 0.5046 0.2808 0.101 Uiso 1 1 calc R
H14B H 1.2967 0.6247 0.3346 0.101 Uiso 1 1 calc R
H14C H 1.3147 0.6143 0.2203 0.101 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 0.0033 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
C7 N1 C8 121.87(15)
C7 N1 C14 120.12(15)
C8 N1 C14 117.84(15)
C13 O2 H2 109.5
C2 C1 C6 119.4(3)
C2 C1 H1 120.3
C6 C1 H1 120.3
C3 C2 C1 121.4(3)
C3 C2 H2A 119.3
C1 C2 H2A 119.3
C2 C3 C4 119.3(3)
C2 C3 H3 120.3
C4 C3 H3 120.3
C3 C4 C5 120.4(3)
C3 C4 H4 119.8
C5 C4 H4 119.8
C4 C5 C6 119.9(3)
C4 C5 H5 120.0
C6 C5 H5 120.0
C5 C6 C1 119.60(19)
C5 C6 C7 118.36(17)
C1 C6 C7 121.92(19)
O1 C7 N1 121.15(16)
O1 C7 C6 119.95(16)
N1 C7 C6 118.90(15)
C9 C8 C13 120.33(17)
C9 C8 N1 120.01(17)
C13 C8 N1 119.66(17)
C10 C9 C8 119.94(19)
C10 C9 H9 120.0
C8 C9 H9 120.0
C9 C10 C11 119.9(2)
C9 C10 H10 120.1
C11 C10 H10 120.1
C12 C11 C10 120.6(2)
C12 C11 H11 119.7
C10 C11 H11 119.7
C11 C12 C13 120.2(2)
C11 C12 H12 119.9
C13 C12 H12 119.9
O2 C13 C12 123.78(17)
O2 C13 C8 117.18(16)
C12 C13 C8 119.03(18)
N1 C14 H14A 109.5
N1 C14 H14B 109.5
H14A C14 H14B 109.5
N1 C14 H14C 109.5
H14A C14 H14C 109.5
H14B C14 H14C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C7 1.344(2)
N1 C8 1.437(2)
N1 C14 1.463(2)
O1 C7 1.237(2)
O2 C13 1.359(2)
O2 H2 0.8200
C1 C2 1.365(4)
C1 C6 1.382(3)
C1 H1 0.9300
C2 C3 1.362(5)
C2 H2A 0.9300
C3 C4 1.371(5)
C3 H3 0.9300
C4 C5 1.374(4)
C4 H4 0.9300
C5 C6 1.375(3)
C5 H5 0.9300
C6 C7 1.484(3)
C8 C9 1.380(3)
C8 C13 1.385(3)
C9 C10 1.372(3)
C9 H9 0.9300
C10 C11 1.374(3)
C10 H10 0.9300
C11 C12 1.369(3)
C11 H11 0.9300
C12 C13 1.385(3)
C12 H12 0.9300
C14 H14A 0.9600
C14 H14B 0.9600
C14 H14C 0.9600
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
C6 C1 C2 C3 0.3(4)
C1 C2 C3 C4 -0.3(5)
C2 C3 C4 C5 -0.3(5)
C3 C4 C5 C6 0.9(4)
C4 C5 C6 C1 -0.9(3)
C4 C5 C6 C7 -177.0(2)
C2 C1 C6 C5 0.3(3)
C2 C1 C6 C7 176.2(2)
C8 N1 C7 O1 -172.00(17)
C14 N1 C7 O1 3.2(3)
C8 N1 C7 C6 8.0(3)
C14 N1 C7 C6 -176.80(18)
C5 C6 C7 O1 52.4(3)
C1 C6 C7 O1 -123.5(2)
C5 C6 C7 N1 -127.6(2)
C1 C6 C7 N1 56.5(3)
C7 N1 C8 C9 72.9(2)
C14 N1 C8 C9 -102.4(2)
C7 N1 C8 C13 -107.3(2)
C14 N1 C8 C13 77.4(2)
C13 C8 C9 C10 1.7(3)
N1 C8 C9 C10 -178.48(17)
C8 C9 C10 C11 0.1(3)
C9 C10 C11 C12 -1.2(3)
C10 C11 C12 C13 0.5(3)
C11 C12 C13 O2 179.5(2)
C11 C12 C13 C8 1.3(3)
C9 C8 C13 O2 179.29(17)
N1 C8 C13 O2 -0.6(3)
C9 C8 C13 C12 -2.3(3)
N1 C8 C13 C12 177.82(17)
