#------------------------------------------------------------------------------
#$Date: 2016-02-13 14:50:18 +0200 (Sat, 13 Feb 2016) $
#$Revision: 176428 $
#$URL: svn://www.crystallography.net/cod/cif/7/22/18/7221823.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_7221823
loop_
_publ_author_name
'Aksenov, Nicolai A.'
'Aksenov, Alexander V.'
'Nadein, Oleg N.'
'Aksenov, Dmitrii A.'
'Smirnov, Alexander N.'
'Rubin, Michael'
_publ_section_title
;
 One-pot synthesis of benzoxazoles via the metal-free ortho-C-H
 functionalization of phenols with nitroalkanes
;
_journal_name_full               'RSC Adv.'
_journal_paper_doi               10.1039/C5RA15128G
_journal_year                    2015
_chemical_formula_moiety         'C10 H11 N O'
_chemical_formula_sum            'C10 H11 N O'
_chemical_formula_weight         161.20
_chemical_melting_point          366
_chemical_name_common            2,5,6-Trimethylbenzo[d]oxazole
_chemical_name_systematic
;
 ?
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2yn'
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2015-07-25 deposited with the CCDC.
2015-08-17 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 94.528(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   6.1944(2)
_cell_length_b                   11.6799(3)
_cell_length_c                   11.8941(3)
_cell_measurement_temperature    100(10)
_cell_measurement_theta_max      74.160
_cell_volume                     857.85(4)
_computing_cell_refinement
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35g (release 09-12-2014 CrysAlis171 .NET)
(compiled Dec  9 2014,15:38:47)
;
_computing_data_collection
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35g (release 09-12-2014 CrysAlis171 .NET)
(compiled Dec  9 2014,15:38:47)
;
_computing_data_reduction
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35g (release 09-12-2014 CrysAlis171 .NET)
(compiled Dec  9 2014,15:38:47)
;
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(10)
_diffrn_measured_fraction_theta_full 0.991
_diffrn_measured_fraction_theta_max 0.957
_diffrn_measurement_device_type  'SuperNova (Cu) X-ray Source'
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_source         'sealed X-ray tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0210
_diffrn_reflns_av_sigmaI/netI    0.0259
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -5
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            3058
_diffrn_reflns_theta_full        68.00
_diffrn_reflns_theta_max         74.16
_diffrn_reflns_theta_min         5.32
_exptl_absorpt_coefficient_mu    0.645
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.84391
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro, Agilent Technologies,
Version 1.171.37.35g (release 09-12-2014 CrysAlis171 .NET)
(compiled Dec  9 2014,15:38:47)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.248
_exptl_crystal_density_meas      1.248
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             344
_exptl_crystal_size_max          0.404
_exptl_crystal_size_mid          0.178
_exptl_crystal_size_min          0.123
_refine_diff_density_max         0.278
_refine_diff_density_min         -0.210
_refine_diff_density_rms         0.045
_refine_ls_extinction_coef       0.0209(18)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     132
_refine_ls_number_reflns         1675
_refine_ls_number_restraints     26
_refine_ls_restrained_S_all      1.059
_refine_ls_R_factor_all          0.0436
_refine_ls_R_factor_gt           0.0405
_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)+(0.0704P)²+0.1718P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1142
_refine_ls_wR_factor_ref         0.1191
_reflns_number_gt                1538
_reflns_number_total             1751
_reflns_threshold_expression     >2σ(I)
_cod_data_source_file            c5ra15128g2.cif
_cod_data_source_block           an_555_256trimebenzoxazole
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7221823
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -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
N1 N 0.065(3) 0.5684(12) 0.1554(14) 0.027(3) Uani 0.512(13) 1 d PDU A 1
O1 O 0.1129(17) 0.7616(7) 0.1303(7) 0.0234(17) Uani 0.512(13) 1 d PDU A 1
N1A N 0.094(2) 0.7551(9) 0.1300(8) 0.0211(19) Uani 0.488(13) 1 d PDU A 2
O1A O 0.100(2) 0.5709(8) 0.1665(11) 0.0166(14) Uani 0.488(13) 1 d PDU A 2
C3 C 0.43015(19) 0.55355(11) 0.28823(9) 0.0262(3) Uani 1 1 d . . .
H3 H 0.4201 0.4754 0.3016 0.031 Uiso 1 1 calc R . .
C6 C 0.45723(19) 0.79224(10) 0.24677(9) 0.0235(3) Uani 1 1 d . A .
H6 H 0.4652 0.8704 0.2327 0.028 Uiso 1 1 calc R . .
C5 C 0.28563(18) 0.72691(10) 0.20008(9) 0.0212(3) Uani 1 1 d . . .
C4 C 0.27314(19) 0.61052(10) 0.21951(9) 0.0230(3) Uani 1 1 d . A .
C2 C 0.60317(19) 0.61770(11) 0.33643(9) 0.0252(3) Uani 1 1 d . A .
C1 C 0.61692(18) 0.73665(11) 0.31541(9) 0.0242(3) Uani 1 1 d . . .
C10 C 0.8046(2) 0.80537(12) 0.36765(10) 0.0308(3) Uani 1 1 d . A .
H10A H 0.7865 0.8843 0.3464 0.046 Uiso 1 1 calc R . .
H10B H 0.9371 0.7768 0.3416 0.046 Uiso 1 1 calc R . .
H10C H 0.8097 0.7988 0.4483 0.046 Uiso 1 1 calc R . .
C9 C 0.7758(2) 0.55841(12) 0.41210(10) 0.0327(3) Uani 1 1 d . . .
H9A H 0.7434 0.4782 0.4157 0.049 Uiso 1 1 calc R A .
H9B H 0.7797 0.5908 0.4864 0.049 Uiso 1 1 calc R . .
H9C H 0.9141 0.5686 0.3823 0.049 Uiso 1 1 calc R . .
C7 C -0.00486(19) 0.66195(11) 0.11135(9) 0.0249(3) Uani 1 1 d D . .
C8 C -0.2096(2) 0.65700(11) 0.03916(10) 0.0293(3) Uani 1 1 d . A .
H8A H -0.1955 0.6031 -0.0207 0.044 Uiso 1 1 calc R . .
H8B H -0.2417 0.7314 0.0078 0.044 Uiso 1 1 calc R . .
H8C H -0.3247 0.6334 0.0835 0.044 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'
O O 0.0492 0.0322 '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 C4 100.1(10)
C5 O1 C7 103.2(5)
C7 N1A C5 105.8(5)
C4 O1A C7 107.3(7)
C4 C3 C2 117.67(11)
C4 C3 H3 121.2
C2 C3 H3 121.2
C5 C6 C1 117.66(11)
C5 C6 H6 121.2
C1 C6 H6 121.2
O1 C5 C4 110.0(4)
O1 C5 C6 128.3(4)
C4 C5 C6 121.67(11)
C4 C5 N1A 105.6(5)
C6 C5 N1A 132.7(5)
O1A C4 C5 109.1(4)
O1A C4 C3 129.3(4)
C5 C4 C3 121.56(11)
C5 C4 N1 106.8(5)
C3 C4 N1 131.6(5)
C3 C2 C1 120.67(11)
C3 C2 C9 118.95(12)
C1 C2 C9 120.37(11)
C6 C1 C2 120.76(11)
C6 C1 C10 118.87(11)
C2 C1 C10 120.37(11)
C1 C10 H10A 109.5
C1 C10 H10B 109.5
H10A C10 H10B 109.5
C1 C10 H10C 109.5
H10A C10 H10C 109.5
H10B C10 H10C 109.5
C2 C9 H9A 109.5
C2 C9 H9B 109.5
H9A C9 H9B 109.5
C2 C9 H9C 109.5
H9A C9 H9C 109.5
H9B C9 H9C 109.5
N1A C7 N1 121.6(9)
N1 C7 O1 119.8(8)
N1A C7 O1A 112.2(7)
O1 C7 O1A 110.4(7)
N1A C7 C8 121.3(4)
N1 C7 C8 117.0(8)
O1 C7 C8 123.1(3)
O1A C7 C8 126.5(6)
C7 C8 H8A 109.5
C7 C8 H8B 109.5
H8A C8 H8B 109.5
C7 C8 H8C 109.5
H8A C8 H8C 109.5
H8B C8 H8C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
N1 C7 1.272(12)
N1 C4 1.527(17)
O1 C5 1.362(8)
O1 C7 1.383(10)
N1A C7 1.260(12)
N1A C5 1.434(9)
O1A C4 1.288(16)
O1A C7 1.384(9)
C3 C4 1.3897(16)
C3 C2 1.3934(17)
C3 H3 0.9300
C6 C5 1.3882(17)
C6 C1 1.3925(16)
C6 H6 0.9300
C5 C4 1.3822(17)
C2 C1 1.4155(19)
C2 C9 1.5103(16)
C1 C10 1.5058(17)
C10 H10A 0.9600
C10 H10B 0.9600
C10 H10C 0.9600
C9 H9A 0.9600
C9 H9B 0.9600
C9 H9C 0.9600
C7 C8 1.4753(17)
C8 H8A 0.9600
C8 H8B 0.9600
C8 H8C 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
C7 O1 C5 C4 1.4(6)
C7 O1 C5 C6 -179.7(2)
C7 O1 C5 N1A -23(9)
C1 C6 C5 O1 -179.5(5)
C1 C6 C5 C4 -0.65(16)
C1 C6 C5 N1A 177.9(7)
C7 N1A C5 O1 154(10)
C7 N1A C5 C4 -2.1(8)
C7 N1A C5 C6 179.2(3)
C7 O1A C4 C5 -0.2(9)
C7 O1A C4 C3 178.9(3)
C7 O1A C4 N1 7(28)
O1 C5 C4 O1A -0.8(7)
C6 C5 C4 O1A -179.8(6)
N1A C5 C4 O1A 1.4(7)
O1 C5 C4 C3 -180.0(4)
C6 C5 C4 C3 1.04(16)
N1A C5 C4 C3 -177.8(5)
O1 C5 C4 N1 -1.1(8)
C6 C5 C4 N1 179.9(6)
N1A C5 C4 N1 1.1(8)
C2 C3 C4 O1A -179.7(7)
C2 C3 C4 C5 -0.65(16)
C2 C3 C4 N1 -179.2(8)
C7 N1 C4 O1A -173(29)
C7 N1 C4 C5 0.3(11)
C7 N1 C4 C3 179.0(3)
C4 C3 C2 C1 -0.08(16)
C4 C3 C2 C9 179.64(10)
C5 C6 C1 C2 -0.07(15)
C5 C6 C1 C10 -179.74(9)
C3 C2 C1 C6 0.43(16)
C9 C2 C1 C6 -179.28(10)
C3 C2 C1 C10 -179.90(10)
C9 C2 C1 C10 0.38(16)
C5 N1A C7 N1 2.6(13)
C5 N1A C7 O1 -48(14)
C5 N1A C7 O1A 2.0(10)
C5 N1A C7 C8 -178.6(3)
C4 N1 C7 N1A -1.9(14)
C4 N1 C7 O1 0.7(13)
C4 N1 C7 O1A 2(7)
C4 N1 C7 C8 179.3(4)
C5 O1 C7 N1A 129(14)
C5 O1 C7 N1 -1.3(11)
C5 O1 C7 O1A -1.5(8)
C5 O1 C7 C8 -179.9(3)
C4 O1A C7 N1A -1.2(11)
C4 O1A C7 N1 -178(8)
C4 O1A C7 O1 1.1(10)
C4 O1A C7 C8 179.4(4)
