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#$Date: 2016-10-26 04:06:02 +0300 (Wed, 26 Oct 2016) $
#$Revision: 187562 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/24/18/2241897.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_2241897
loop_
_publ_author_name
'Rivera, Augusto'
'Rojas, Jicli José''
'Ríos-Motta, Jaime'
'Bolte, Michael'
_publ_section_title
;
 Crystal structure of
 1,2-bis(6-bromo-3,4-dihydro-2H-benz[e][1,3]oxazin-3-yl)ethane:
 a bromine-containing bis-benzoxazine
;
_journal_coeditor_code           SJ5510
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              1645
_journal_page_last               1647
_journal_paper_doi               10.1107/S2056989016016509
_journal_volume                  72
_journal_year                    2016
_chemical_formula_iupac          'C18 H18 Br2 N2 O2'
_chemical_formula_moiety         'C18 H18 Br2 N2 O2'
_chemical_formula_sum            'C18 H18 Br2 N2 O2'
_chemical_formula_weight         454.16
_chemical_name_systematic
;
1,2-Bis(6-bromo-3,4-dihydro-2H-benz[e][1,3]oxazin-3-yl)ethane
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           15
_space_group_name_Hall           '-C 2yc'
_space_group_name_H-M_alt        'C 1 2/c 1'
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/c 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 121.557(7)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   19.464(2)
_cell_length_b                   5.9444(7)
_cell_length_c                   17.2225(19)
_cell_measurement_reflns_used    3703
_cell_measurement_temperature    173(2)
_cell_measurement_theta_max      25.98
_cell_measurement_theta_min      3.64
_cell_volume                     1698.0(3)
_computing_cell_refinement
;
X-Area (Stoe & Cie, 2001)
;
_computing_data_collection
;
X-Area (Stoe & Cie, 2001)
;
_computing_data_reduction
;
X-Area (Stoe & Cie, 2001)
;
_computing_molecular_graphics
;
XP in SHELXTL-Plus (Sheldrick, 2008)
;
_computing_publication_material
;
SHELXL-2014/7 (Sheldrick, 2015)
;
_computing_structure_refinement
;
SHELXL-2014/7 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS (Sheldrick, 2008)
;
_diffrn_ambient_temperature      173(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'STOE IPDS II two-circle'
_diffrn_measurement_method       ω
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0777
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       7
_diffrn_reflns_limit_k_min       -7
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            3703
_diffrn_reflns_theta_full        25.000
_diffrn_reflns_theta_max         25.565
_diffrn_reflns_theta_min         3.641
_exptl_absorpt_coefficient_mu    4.787
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.905
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(X-Area; Stoe & Cie, 2001)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.777
_exptl_crystal_description       block
_exptl_crystal_F_000             904
_exptl_crystal_size_max          0.27
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.26
_refine_diff_density_max         1.398
_refine_diff_density_min         -1.920
_refine_ls_extinction_coef       0.0037(8)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method
;
SHELXL-2014/7 (Sheldrick 2015)
;
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     110
_refine_ls_number_reflns         1583
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0626
_refine_ls_R_factor_gt           0.0563
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0990P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1386
_refine_ls_wR_factor_ref         0.1428
_reflns_number_gt                1391
_reflns_number_total             1583
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            sj5510sup1.cif
_cod_data_source_block           I
_cod_database_code               2241897
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_min   0.358
_shelx_estimated_absorpt_t_max   0.369
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -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_occupancy
Br Br1 0.60406(3) -0.02845(9) 0.93353(3) 0.0226(3) Uani d 1
O O1 0.67962(18) 0.6369(6) 0.7231(2) 0.0176(7) Uani d 1
N N1 0.6072(2) 0.4166(7) 0.5842(2) 0.0130(8) Uani d 1
C C1 0.5323(2) 0.5473(7) 0.5467(3) 0.0141(10) Uani d 1
H H1A 0.5430 0.7067 0.5401 0.017 Uiso calc 1
H H1B 0.5124 0.5406 0.5891 0.017 Uiso calc 1
C C2 0.6783(3) 0.5494(8) 0.6434(3) 0.0155(10) Uani d 1
H H2A 0.6811 0.6770 0.6082 0.019 Uiso calc 1
H H2B 0.7268 0.4552 0.6639 0.019 Uiso calc 1
C C3 0.6620(3) 0.4788(8) 0.7681(3) 0.0141(9) Uani d 1
C C4 0.6259(2) 0.2721(8) 0.7288(3) 0.0142(9) Uani d 1
C C5 0.6091(2) 0.2158(8) 0.6343(3) 0.0140(9) Uani d 1
H H5A 0.6513 0.1123 0.6400 0.017 Uiso calc 1
H H5B 0.5566 0.1372 0.5995 0.017 Uiso calc 1
C C6 0.6083(2) 0.1218(8) 0.7781(3) 0.0147(9) Uani d 1
H H6 0.5841 -0.0193 0.7526 0.018 Uiso calc 1
C C7 0.6265(3) 0.1804(8) 0.8655(3) 0.0164(9) Uani d 1
C C8 0.6619(3) 0.3870(9) 0.9044(3) 0.0223(10) Uani d 1
H H8 0.6741 0.4248 0.9639 0.027 Uiso calc 1
C C9 0.6787(3) 0.5348(8) 0.8552(3) 0.0192(11) Uani d 1
H H9 0.7021 0.6768 0.8807 0.023 Uiso calc 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'
Br Br -0.2901 2.4595 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
C3 O1 C2 . . 113.7(4)
C2 N1 C5 . . 108.0(3)
C2 N1 C1 . . 112.6(4)
C5 N1 C1 . . 113.8(3)
N1 C1 C1 . 5_666 110.2(4)
N1 C1 H1A . . 109.6
C1 C1 H1A 5_666 . 109.6
N1 C1 H1B . . 109.6
C1 C1 H1B 5_666 . 109.6
H1A C1 H1B . . 108.1
N1 C2 O1 . . 113.4(4)
N1 C2 H2A . . 108.9
O1 C2 H2A . . 108.9
N1 C2 H2B . . 108.9
O1 C2 H2B . . 108.9
H2A C2 H2B . . 107.7
O1 C3 C9 . . 117.2(4)
O1 C3 C4 . . 122.5(4)
C9 C3 C4 . . 120.3(5)
C6 C4 C3 . . 119.2(4)
C6 C4 C5 . . 121.9(4)
C3 C4 C5 . . 118.9(4)
N1 C5 C4 . . 112.2(4)
N1 C5 H5A . . 109.2
C4 C5 H5A . . 109.2
N1 C5 H5B . . 109.2
C4 C5 H5B . . 109.2
H5A C5 H5B . . 107.9
C4 C6 C7 . . 119.5(4)
C4 C6 H6 . . 120.3
C7 C6 H6 . . 120.3
C8 C7 C6 . . 121.3(4)
C8 C7 Br1 . . 119.4(4)
C6 C7 Br1 . . 119.2(4)
C9 C8 C7 . . 118.9(4)
C9 C8 H8 . . 120.5
C7 C8 H8 . . 120.5
C8 C9 C3 . . 120.8(5)
C8 C9 H9 . . 119.6
C3 C9 H9 . . 119.6
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
Br1 C7 . 1.909(5)
O1 C3 . 1.372(6)
O1 C2 . 1.455(6)
N1 C2 . 1.450(5)
N1 C5 . 1.462(6)
N1 C1 . 1.470(5)
C1 C1 5_666 1.538(8)
C1 H1A . 0.9900
C1 H1B . 0.9900
C2 H2A . 0.9900
C2 H2B . 0.9900
C3 C9 . 1.398(7)
C3 C4 . 1.402(6)
C4 C6 . 1.393(7)
C4 C5 . 1.519(6)
C5 H5A . 0.9900
C5 H5B . 0.9900
C6 C7 . 1.397(7)
C6 H6 . 0.9500
C7 C8 . 1.396(7)
C8 C9 . 1.373(8)
C8 H8 . 0.9500
C9 H9 . 0.9500
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
C5 H5B Br1 2_656 0.99 3.04 3.951(5) 154
C2 H2B O1 4_646 0.99 2.64 3.506(6) 146
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_4
_geom_torsion
C2 N1 C1 C1 5_666 151.1(5)
C5 N1 C1 C1 5_666 -85.6(6)
C5 N1 C2 O1 . -64.9(5)
C1 N1 C2 O1 . 61.6(5)
C3 O1 C2 N1 . 47.8(5)
C2 O1 C3 C9 . 166.5(4)
C2 O1 C3 C4 . -15.8(5)
O1 C3 C4 C6 . -178.7(4)
C9 C3 C4 C6 . -1.1(6)
O1 C3 C4 C5 . 2.9(6)
C9 C3 C4 C5 . -179.5(4)
C2 N1 C5 C4 . 48.7(5)
C1 N1 C5 C4 . -77.1(4)
C6 C4 C5 N1 . 161.5(4)
C3 C4 C5 N1 . -20.1(5)
C3 C4 C6 C7 . 0.3(6)
C5 C4 C6 C7 . 178.7(4)
C4 C6 C7 C8 . 0.1(7)
C4 C6 C7 Br1 . -178.8(3)
C6 C7 C8 C9 . 0.2(7)
Br1 C7 C8 C9 . 179.2(4)
C7 C8 C9 C3 . -1.0(7)
O1 C3 C9 C8 . 179.2(4)
C4 C3 C9 C8 . 1.4(7)

_cod_database_fobs_code 2241897
