#------------------------------------------------------------------------------
#$Date: 2017-10-13 14:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201982 $
#$URL: file:///home/coder/svn-repositories/cod/cif/4/02/44/4024441.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_4024441
loop_
_publ_author_name
'Enguang Feng'
'He Huang'
'Yu Zhou'
'Deju Ye'
'Hualiang Jiang'
'Hong Liu'
_publ_contact_author             'Enguang Feng'
_publ_contact_author_email       feg007@126.com
_publ_section_title
;
Copper(I)-Catalyzed One-Pot Synthesis of 2H-1,4-Benzoxazin-3-(4H)-ones
fromo-Halophenols and 2-Chloroacetamides
;
_journal_name_full               'Journal of Organic Chemistry'
_journal_page_first              2846
_journal_page_last               2849
_journal_paper_doi               10.1021/jo802818s
_journal_volume                  74
_journal_year                    2009
_chemical_formula_sum            'C16 H15 N O2'
_chemical_formula_weight         253.29
_chemical_name_systematic
; 
 6-methyl-4-p-tolyl-2H-1,4-benzoxazin-3(4H)-one 
;
_space_group_IT_number           61
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-P 2ac 2ab'
_symmetry_space_group_name_H-M   'P b c a'
_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                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   11.8759(14)
_cell_length_b                   9.4026(11)
_cell_length_c                   23.997(3)
_cell_measurement_reflns_used    2236
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      45.127
_cell_measurement_theta_min      4.826
_cell_volume                     2679.6(6)
_computing_cell_refinement       'Bruker SMART'
_computing_data_collection       'Bruker SMART'
_computing_data_reduction        'Bruker SHELXTL'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-97 (Sheldrick, 1990)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.996
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device_type  'CCD area detector'
_diffrn_measurement_method       'phi and omega 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  0.1134
_diffrn_reflns_av_sigmaI/netI    0.0677
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       30
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            14730
_diffrn_reflns_theta_full        26.99
_diffrn_reflns_theta_max         26.99
_diffrn_reflns_theta_min         1.70
_exptl_absorpt_coefficient_mu    0.083
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_correction_T_min  0.7597
_exptl_absorpt_correction_type   empirical
_exptl_absorpt_process_details   sadabs
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.256
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prismatic
_exptl_crystal_F_000             1072
_exptl_crystal_preparation       'absolute methanol'
_exptl_crystal_size_max          0.408
_exptl_crystal_size_mid          0.237
_exptl_crystal_size_min          0.208
_refine_diff_density_max         0.196
_refine_diff_density_min         -0.194
_refine_diff_density_rms         0.044
_refine_ls_extinction_coef       0.0044(10)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_ref   0.923
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     175
_refine_ls_number_reflns         2907
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.923
_refine_ls_R_factor_all          0.0854
_refine_ls_R_factor_gt           0.0532
_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)+(0.0700P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1305
_refine_ls_wR_factor_ref         0.1441
_reflns_number_gt                1782
_reflns_number_total             2907
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            jo802818s_si_001.cif
_cod_data_source_block           dddcsynfeg
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Orthorhombic' changed to 'orthorhombic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 
;
_cod_original_sg_symbol_H-M      Pbca
_cod_database_code               4024441
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'x, -y-1/2, z-1/2'
'-x-1/2, y-1/2, z'
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
O1 O 0.36346(11) 0.05285(15) 0.52400(5) 0.0610(4) Uani 1 1 d . . .
O2 O 0.51726(11) 0.01609(15) 0.64837(6) 0.0665(5) Uani 1 1 d . . .
N1 N 0.30829(12) 0.09955(16) 0.61264(5) 0.0458(4) Uani 1 1 d . . .
C1 C 0.38745(15) 0.0722(2) 0.57284(8) 0.0487(5) Uani 1 1 d . . .
C2 C 0.50717(16) 0.0692(2) 0.59283(8) 0.0621(6) Uani 1 1 d . . .
H2A H 0.5514 0.0099 0.5680 0.075 Uiso 1 1 calc R . .
H2B H 0.5378 0.1647 0.5913 0.075 Uiso 1 1 calc R . .
C3 C 0.44880(15) 0.0893(2) 0.68493(8) 0.0512(5) Uani 1 1 d . . .
C4 C 0.34287(15) 0.13225(19) 0.66817(7) 0.0430(4) Uani 1 1 d . . .
C5 C 0.27531(15) 0.20709(19) 0.70484(7) 0.0458(5) Uani 1 1 d . . .
H5 H 0.2044 0.2371 0.6934 0.055 Uiso 1 1 calc R . .
C6 C 0.31157(17) 0.2382(2) 0.75844(7) 0.0525(5) Uani 1 1 d . . .
C7 C 0.41785(18) 0.1904(2) 0.77440(8) 0.0631(6) Uani 1 1 d . . .
H7 H 0.4435 0.2092 0.8103 0.076 Uiso 1 1 calc R . .
C8 C 0.48529(18) 0.1164(2) 0.73836(8) 0.0633(6) Uani 1 1 d . . .
H8 H 0.5556 0.0845 0.7499 0.076 Uiso 1 1 calc R . .
C9 C 0.23867(19) 0.3235(3) 0.79756(9) 0.0760(7) Uani 1 1 d . . .
H9A H 0.1888 0.2608 0.8172 0.114 Uiso 1 1 calc R . .
H9B H 0.1953 0.3910 0.7766 0.114 Uiso 1 1 calc R . .
H9C H 0.2855 0.3730 0.8238 0.114 Uiso 1 1 calc R . .
C10 C 0.19052(14) 0.09990(18) 0.59836(7) 0.0417(4) Uani 1 1 d . . .
C11 C 0.14808(16) 0.2012(2) 0.56298(7) 0.0531(5) Uani 1 1 d . . .
H11 H 0.1951 0.2708 0.5482 0.064 Uiso 1 1 calc R . .
C12 C 0.03505(18) 0.1991(2) 0.54957(8) 0.0631(6) Uani 1 1 d . . .
H12 H 0.0067 0.2678 0.5255 0.076 Uiso 1 1 calc R . .
C13 C -0.03688(17) 0.0979(2) 0.57094(8) 0.0602(6) Uani 1 1 d . . .
C14 C 0.00817(17) -0.0018(2) 0.60687(10) 0.0638(6) Uani 1 1 d . . .
H14 H -0.0387 -0.0704 0.6224 0.077 Uiso 1 1 calc R . .
C15 C 0.12106(16) -0.0019(2) 0.62024(8) 0.0539(5) Uani 1 1 d . . .
H15 H 0.1499 -0.0709 0.6440 0.065 Uiso 1 1 calc R . .
C16 C -0.16049(19) 0.0968(3) 0.55646(11) 0.1019(10) Uani 1 1 d . . .
H16A H -0.1713 0.0478 0.5218 0.153 Uiso 1 1 calc R . .
H16B H -0.1871 0.1928 0.5531 0.153 Uiso 1 1 calc R . .
H16C H -0.2017 0.0491 0.5853 0.153 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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C3 O2 C2 111.67(15) . . ?
C1 N1 C4 119.72(15) . . ?
C1 N1 C10 120.19(14) . . ?
C4 N1 C10 120.06(14) . . ?
O1 C1 N1 122.67(17) . . ?
O1 C1 C2 121.72(17) . . ?
N1 C1 C2 115.61(16) . . ?
O2 C2 C1 112.61(16) . . ?
O2 C2 H2A 109.1 . . ?
C1 C2 H2A 109.1 . . ?
O2 C2 H2B 109.1 . . ?
C1 C2 H2B 109.1 . . ?
H2A C2 H2B 107.8 . . ?
C8 C3 O2 119.91(17) . . ?
C8 C3 C4 120.25(18) . . ?
O2 C3 C4 119.82(16) . . ?
C3 C4 C5 119.46(16) . . ?
C3 C4 N1 118.09(16) . . ?
C5 C4 N1 122.44(15) . . ?
C4 C5 C6 121.13(17) . . ?
C4 C5 H5 119.4 . . ?
C6 C5 H5 119.4 . . ?
C5 C6 C7 117.89(18) . . ?
C5 C6 C9 120.73(18) . . ?
C7 C6 C9 121.37(18) . . ?
C8 C7 C6 121.36(18) . . ?
C8 C7 H7 119.3 . . ?
C6 C7 H7 119.3 . . ?
C7 C8 C3 119.87(19) . . ?
C7 C8 H8 120.1 . . ?
C3 C8 H8 120.1 . . ?
C6 C9 H9A 109.5 . . ?
C6 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
C6 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C15 C10 C11 120.12(17) . . ?
C15 C10 N1 119.51(15) . . ?
C11 C10 N1 120.37(16) . . ?
C10 C11 C12 119.43(18) . . ?
C10 C11 H11 120.3 . . ?
C12 C11 H11 120.3 . . ?
C13 C12 C11 121.73(18) . . ?
C13 C12 H12 119.1 . . ?
C11 C12 H12 119.1 . . ?
C12 C13 C14 117.45(18) . . ?
C12 C13 C16 121.5(2) . . ?
C14 C13 C16 121.1(2) . . ?
C15 C14 C13 121.50(19) . . ?
C15 C14 H14 119.3 . . ?
C13 C14 H14 119.3 . . ?
C10 C15 C14 119.77(17) . . ?
C10 C15 H15 120.1 . . ?
C14 C15 H15 120.1 . . ?
C13 C16 H16A 109.5 . . ?
C13 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C13 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
O1 C1 1.220(2) . ?
O2 C3 1.380(2) . ?
O2 C2 1.428(2) . ?
N1 C1 1.365(2) . ?
N1 C4 1.428(2) . ?
N1 C10 1.440(2) . ?
C1 C2 1.501(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C8 1.377(3) . ?
C3 C4 1.381(2) . ?
C4 C5 1.383(2) . ?
C5 C6 1.388(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.393(3) . ?
C6 C9 1.508(3) . ?
C7 C8 1.369(3) . ?
C7 H7 0.9300 . ?
C8 H8 0.9300 . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C15 1.368(2) . ?
C10 C11 1.372(2) . ?
C11 C12 1.381(3) . ?
C11 H11 0.9300 . ?
C12 C13 1.378(3) . ?
C12 H12 0.9300 . ?
C13 C14 1.381(3) . ?
C13 C16 1.509(3) . ?
C14 C15 1.378(3) . ?
C14 H14 0.9300 . ?
C15 H15 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C4 N1 C1 O1 -175.06(17) . . . . ?
C10 N1 C1 O1 3.0(3) . . . . ?
C4 N1 C1 C2 4.1(2) . . . . ?
C10 N1 C1 C2 -177.82(15) . . . . ?
C3 O2 C2 C1 -53.9(2) . . . . ?
O1 C1 C2 O2 -147.46(19) . . . . ?
N1 C1 C2 O2 33.3(2) . . . . ?
C2 O2 C3 C8 -143.36(19) . . . . ?
C2 O2 C3 C4 38.2(2) . . . . ?
C8 C3 C4 C5 2.3(3) . . . . ?
O2 C3 C4 C5 -179.22(17) . . . . ?
C8 C3 C4 N1 -178.98(17) . . . . ?
O2 C3 C4 N1 -0.5(3) . . . . ?
C1 N1 C4 C3 -21.6(2) . . . . ?
C10 N1 C4 C3 160.30(16) . . . . ?
C1 N1 C4 C5 157.04(17) . . . . ?
C10 N1 C4 C5 -21.0(2) . . . . ?
C3 C4 C5 C6 -0.8(3) . . . . ?
N1 C4 C5 C6 -179.50(16) . . . . ?
C4 C5 C6 C7 -0.7(3) . . . . ?
C4 C5 C6 C9 178.22(18) . . . . ?
C5 C6 C7 C8 0.7(3) . . . . ?
C9 C6 C7 C8 -178.1(2) . . . . ?
C6 C7 C8 C3 0.7(3) . . . . ?
O2 C3 C8 C7 179.28(19) . . . . ?
C4 C3 C8 C7 -2.2(3) . . . . ?
C1 N1 C10 C15 113.8(2) . . . . ?
C4 N1 C10 C15 -68.1(2) . . . . ?
C1 N1 C10 C11 -66.0(2) . . . . ?
C4 N1 C10 C11 112.05(19) . . . . ?
C15 C10 C11 C12 -0.2(3) . . . . ?
N1 C10 C11 C12 179.61(16) . . . . ?
C10 C11 C12 C13 0.2(3) . . . . ?
C11 C12 C13 C14 0.4(3) . . . . ?
C11 C12 C13 C16 179.53(19) . . . . ?
C12 C13 C14 C15 -1.1(3) . . . . ?
C16 C13 C14 C15 179.8(2) . . . . ?
C11 C10 C15 C14 -0.4(3) . . . . ?
N1 C10 C15 C14 179.77(16) . . . . ?
C13 C14 C15 C10 1.1(3) . . . . ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30658927
