#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/14/2221446.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_2221446
loop_
_publ_author_name
'Li, Zhu-Bo'
'He, Xiao-Yan'
'Dong, Wen-Liang'
'Liao, Dan-Dan'
_publ_section_title
;
 8-Chloro-4-cyclohexyl-2H-1,4-benzoxazin-3(4H)-one
;
_journal_coeditor_code           NC2137
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o762
_journal_paper_doi               10.1107/S1600536809008423
_journal_volume                  65
_journal_year                    2009
_chemical_formula_iupac          'C14 H16 Cl N O2'
_chemical_formula_moiety         'C14 H16 Cl N O2'
_chemical_formula_sum            'C14 H16 Cl N O2'
_chemical_formula_weight         265.73
_chemical_name_systematic
;
8-Chloro-4-cyclohexyl-2H-1,4-benzoxazin-3(4H)-one
;
_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
_cell_angle_alpha                90.00
_cell_angle_beta                 98.7760(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.0570(8)
_cell_length_b                   5.7026(5)
_cell_length_c                   25.289(2)
_cell_measurement_reflns_used    2520
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      26.18
_cell_measurement_theta_min      2.30
_cell_volume                     1290.85(19)
_computing_cell_refinement       'SAINT (Bruker, 2005)'
_computing_data_collection       'SMART (Bruker, 2005)'
_computing_data_reduction        'SAINT (Bruker, 2005)'
_computing_molecular_graphics    'XP in SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_diffrn_measurement_method       'φ and ω'
_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  0.0182
_diffrn_reflns_av_sigmaI/netI    0.0201
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -3
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -30
_diffrn_reflns_number            6491
_diffrn_reflns_theta_full        25.05
_diffrn_reflns_theta_max         25.05
_diffrn_reflns_theta_min         2.30
_diffrn_standards_decay_%        0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.289
_exptl_absorpt_correction_T_max  0.9845
_exptl_absorpt_correction_T_min  0.9673
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.367
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             560
_exptl_crystal_size_max          0.12
_exptl_crystal_size_mid          0.10
_exptl_crystal_size_min          0.06
_refine_diff_density_max         0.147
_refine_diff_density_min         -0.245
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.022
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     163
_refine_ls_number_reflns         2284
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.022
_refine_ls_R_factor_all          0.0451
_refine_ls_R_factor_gt           0.0354
_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)+(0.0412P)²+0.4617P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0865
_refine_ls_wR_factor_ref         0.0936
_reflns_number_gt                1865
_reflns_number_total             2284
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            nc2137.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
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_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        1290.8(2)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               2221446
_cod_database_fobs_code          2221446
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_type_symbol
_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
Cl Cl1 -0.15312(6) 0.41531(10) 0.22217(2) 0.06310(19) Uani d . 1 . .
O O1 -0.02832(15) 0.3875(2) 0.12160(5) 0.0532(3) Uani d . 1 . .
O O2 0.13476(15) 0.2157(3) 0.01039(5) 0.0598(4) Uani d . 1 . .
N N1 0.18465(15) 0.0827(3) 0.09632(5) 0.0423(4) Uani d . 1 . .
C C1 -0.02699(18) 0.2077(3) 0.20691(7) 0.0440(4) Uani d . 1 . .
C C2 0.02332(18) 0.2168(3) 0.15761(6) 0.0409(4) Uani d . 1 . .
C C3 0.12797(18) 0.0547(3) 0.14560(6) 0.0389(4) Uani d . 1 . .
C C4 0.17380(19) -0.1228(3) 0.18194(7) 0.0447(4) Uani d . 1 . .
H H4 0.2398 -0.2371 0.1736 0.054 Uiso calc R 1 . .
C C5 0.1216(2) -0.1303(4) 0.23061(7) 0.0500(5) Uani d . 1 . .
H H5 0.1542 -0.2486 0.2550 0.060 Uiso calc R 1 . .
C C6 0.0224(2) 0.0345(4) 0.24338(7) 0.0486(5) Uani d . 1 . .
H H6 -0.0112 0.0294 0.2763 0.058 Uiso calc R 1 . .
C C7 0.0994(2) 0.1974(3) 0.05491(7) 0.0459(4) Uani d . 1 . .
C C8 -0.0428(2) 0.3028(4) 0.06762(7) 0.0556(5) Uani d . 1 . .
H H8A -0.0722 0.4315 0.0432 0.067 Uiso calc R 1 . .
H H8B -0.1213 0.1855 0.0621 0.067 Uiso calc R 1 . .
C C9 0.33367(19) -0.0012(3) 0.08766(7) 0.0408(4) Uani d . 1 . .
H H9 0.3555 0.0833 0.0560 0.049 Uiso calc R 1 . .
C C10 0.3391(3) -0.2597(4) 0.07334(8) 0.0605(6) Uani d . 1 . .
H H10A 0.2618 -0.2945 0.0434 0.073 Uiso calc R 1 . .
H H10B 0.3211 -0.3547 0.1035 0.073 Uiso calc R 1 . .
C C11 0.4918(3) -0.3181(4) 0.05863(9) 0.0836(8) Uani d . 1 . .
H H11A 0.4973 -0.4852 0.0521 0.100 Uiso calc R 1 . .
H H11B 0.5037 -0.2370 0.0258 0.100 Uiso calc R 1 . .
C C12 0.6170(3) -0.2494(5) 0.10186(10) 0.0847(8) Uani d . 1 . .
H H12A 0.7118 -0.2796 0.0898 0.102 Uiso calc R 1 . .
H H12B 0.6126 -0.3447 0.1333 0.102 Uiso calc R 1 . .
C C13 0.6084(2) 0.0065(5) 0.11650(10) 0.0701(6) Uani d . 1 . .
H H13A 0.6247 0.1024 0.0862 0.084 Uiso calc R 1 . .
H H13B 0.6868 0.0420 0.1460 0.084 Uiso calc R 1 . .
C C14 0.45753(19) 0.0669(3) 0.13235(7) 0.0482(5) Uani d . 1 . .
H H14A 0.4451 -0.0164 0.1648 0.058 Uiso calc R 1 . .
H H14B 0.4527 0.2337 0.1393 0.058 Uiso calc R 1 . .
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'
Cl Cl 0.1484 0.1585 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C2 O1 C8 . . 111.50(15) ?
C7 N1 C3 . . 119.02(14) ?
C7 N1 C9 . . 117.53(14) ?
C3 N1 C9 . . 123.43(13) ?
C6 C1 C2 . . 120.58(17) ?
C6 C1 Cl1 . . 119.96(14) ?
C2 C1 Cl1 . . 119.46(14) ?
O1 C2 C3 . . 120.24(15) ?
O1 C2 C1 . . 119.88(16) ?
C3 C2 C1 . . 119.87(16) ?
C4 C3 C2 . . 119.04(15) ?
C4 C3 N1 . . 123.27(16) ?
C2 C3 N1 . . 117.69(14) ?
C5 C4 C3 . . 120.20(17) ?
C5 C4 H4 . . 119.9 ?
C3 C4 H4 . . 119.9 ?
C6 C5 C4 . . 120.82(17) ?
C6 C5 H5 . . 119.6 ?
C4 C5 H5 . . 119.6 ?
C5 C6 C1 . . 119.38(16) ?
C5 C6 H6 . . 120.3 ?
C1 C6 H6 . . 120.3 ?
O2 C7 N1 . . 123.31(17) ?
O2 C7 C8 . . 121.21(16) ?
N1 C7 C8 . . 115.47(15) ?
O1 C8 C7 . . 112.45(14) ?
O1 C8 H8A . . 109.1 ?
C7 C8 H8A . . 109.1 ?
O1 C8 H8B . . 109.1 ?
C7 C8 H8B . . 109.1 ?
H8A C8 H8B . . 107.8 ?
N1 C9 C14 . . 113.26(14) ?
N1 C9 C10 . . 114.32(16) ?
C14 C9 C10 . . 112.25(15) ?
N1 C9 H9 . . 105.3 ?
C14 C9 H9 . . 105.3 ?
C10 C9 H9 . . 105.3 ?
C9 C10 C11 . . 109.46(18) ?
C9 C10 H10A . . 109.8 ?
C11 C10 H10A . . 109.8 ?
C9 C10 H10B . . 109.8 ?
C11 C10 H10B . . 109.8 ?
H10A C10 H10B . . 108.2 ?
C12 C11 C10 . . 112.22(17) ?
C12 C11 H11A . . 109.2 ?
C10 C11 H11A . . 109.2 ?
C12 C11 H11B . . 109.2 ?
C10 C11 H11B . . 109.2 ?
H11A C11 H11B . . 107.9 ?
C11 C12 C13 . . 111.6(2) ?
C11 C12 H12A . . 109.3 ?
C13 C12 H12A . . 109.3 ?
C11 C12 H12B . . 109.3 ?
C13 C12 H12B . . 109.3 ?
H12A C12 H12B . . 108.0 ?
C12 C13 C14 . . 111.4(2) ?
C12 C13 H13A . . 109.3 ?
C14 C13 H13A . . 109.3 ?
C12 C13 H13B . . 109.3 ?
C14 C13 H13B . . 109.3 ?
H13A C13 H13B . . 108.0 ?
C9 C14 C13 . . 109.76(16) ?
C9 C14 H14A . . 109.7 ?
C13 C14 H14A . . 109.7 ?
C9 C14 H14B . . 109.7 ?
C13 C14 H14B . . 109.7 ?
H14A C14 H14B . . 108.2 ?
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
Cl1 C1 . 1.7292(19) ?
O1 C2 . 1.366(2) ?
O1 C8 . 1.435(2) ?
O2 C7 . 1.221(2) ?
N1 C7 . 1.369(2) ?
N1 C3 . 1.427(2) ?
N1 C9 . 1.479(2) ?
C1 C6 . 1.378(3) ?
C1 C2 . 1.392(2) ?
C2 C3 . 1.390(2) ?
C3 C4 . 1.388(2) ?
C4 C5 . 1.385(2) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.372(3) ?
C5 H5 . 0.9300 ?
C6 H6 . 0.9300 ?
C7 C8 . 1.500(3) ?
C8 H8A . 0.9700 ?
C8 H8B . 0.9700 ?
C9 C14 . 1.516(2) ?
C9 C10 . 1.521(3) ?
C9 H9 . 0.9800 ?
C10 C11 . 1.523(3) ?
C10 H10A . 0.9700 ?
C10 H10B . 0.9700 ?
C11 C12 . 1.502(4) ?
C11 H11A . 0.9700 ?
C11 H11B . 0.9700 ?
C12 C13 . 1.510(4) ?
C12 H12A . 0.9700 ?
C12 H12B . 0.9700 ?
C13 C14 . 1.521(3) ?
C13 H13A . 0.9700 ?
C13 H13B . 0.9700 ?
C14 H14A . 0.9700 ?
C14 H14B . 0.9700 ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C8 H8A O2 3_565 0.97 2.44 3.407(3) 173.6
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C8 O1 C2 C3 . . . . 36.1(2) ?
C8 O1 C2 C1 . . . . -145.10(16) ?
C6 C1 C2 O1 . . . . 179.06(16) ?
Cl1 C1 C2 O1 . . . . -0.7(2) ?
C6 C1 C2 C3 . . . . -2.1(3) ?
Cl1 C1 C2 C3 . . . . 178.15(13) ?
O1 C2 C3 C4 . . . . -177.29(15) ?
C1 C2 C3 C4 . . . . 3.9(2) ?
O1 C2 C3 N1 . . . . 3.6(2) ?
C1 C2 C3 N1 . . . . -175.20(15) ?
C7 N1 C3 C4 . . . . 155.62(17) ?
C9 N1 C3 C4 . . . . -25.9(3) ?
C7 N1 C3 C2 . . . . -25.3(2) ?
C9 N1 C3 C2 . . . . 153.11(16) ?
C2 C3 C4 C5 . . . . -3.4(3) ?
N1 C3 C4 C5 . . . . 175.67(16) ?
C3 C4 C5 C6 . . . . 1.0(3) ?
C4 C5 C6 C1 . . . . 0.8(3) ?
C2 C1 C6 C5 . . . . -0.3(3) ?
Cl1 C1 C6 C5 . . . . 179.49(14) ?
C3 N1 C7 O2 . . . . -175.04(17) ?
C9 N1 C7 O2 . . . . 6.4(3) ?
C3 N1 C7 C8 . . . . 5.2(2) ?
C9 N1 C7 C8 . . . . -173.32(16) ?
C2 O1 C8 C7 . . . . -54.4(2) ?
O2 C7 C8 O1 . . . . -145.51(18) ?
N1 C7 C8 O1 . . . . 34.2(2) ?
C7 N1 C9 C14 . . . . 130.77(17) ?
C3 N1 C9 C14 . . . . -47.7(2) ?
C7 N1 C9 C10 . . . . -98.95(19) ?
C3 N1 C9 C10 . . . . 82.6(2) ?
N1 C9 C10 C11 . . . . 172.94(15) ?
C14 C9 C10 C11 . . . . -56.3(2) ?
C9 C10 C11 C12 . . . . 54.7(2) ?
C10 C11 C12 C13 . . . . -55.0(3) ?
C11 C12 C13 C14 . . . . 55.3(3) ?
N1 C9 C14 C13 . . . . -171.56(16) ?
C10 C9 C14 C13 . . . . 57.1(2) ?
C12 C13 C14 C9 . . . . -55.7(2) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24741923
