#------------------------------------------------------------------------------
#$Date: 2017-10-13 09:09:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201973 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/20/74/2207453.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_2207453
loop_
_publ_author_name
'Silva, Luiz Everson da'
'Joussef, Antonio Carlos'
'Nunes, Ricardo José'
'Andrighetti-Fröhner, Carla Regina'
'Bortoluzzi, Adailton José'
_publ_section_title
;
 5-[(2-Bromophenylamino)methylene]-2,2-dimethyl-1,3-dioxane-4,6-dione
;
_journal_coeditor_code           BT6779
_journal_issue                   12
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o4252
_journal_page_last               o4253
_journal_paper_doi               10.1107/S1600536805036883
_journal_volume                  61
_journal_year                    2005
_chemical_formula_iupac          'C13 H12 Br N O4'
_chemical_formula_moiety         'C13 H12 Br N O4'
_chemical_formula_sum            'C13 H12 Br N O4'
_chemical_formula_weight         326.15
_chemical_name_systematic
;
5-[(2-Bromophenylamino)methylene]-2,2-dimethyl-1,3-dioxane-4,6-dione
;
_space_group_IT_number           2
_symmetry_cell_setting           triclinic
_symmetry_space_group_name_Hall  '-P 1'
_symmetry_space_group_name_H-M   'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_cell_angle_alpha                95.570(5)
_cell_angle_beta                 101.043(5)
_cell_angle_gamma                99.508(5)
_cell_formula_units_Z            2
_cell_length_a                   6.960(5)
_cell_length_b                   9.298(5)
_cell_length_c                   10.424(5)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    193(2)
_cell_measurement_theta_max      16.91
_cell_measurement_theta_min      4.09
_cell_volume                     647.2(7)
_computing_cell_refinement
;
CAD-4/PC Software
;
_computing_data_collection
;
CAD-4/PC Software (Enraf--Nonius, 1993)
;
_computing_data_reduction        'XCAD4 (Harms & Wocadlo, 1995)'
_computing_molecular_graphics    'PLATON (Spek, 2003)'
_computing_publication_material  SHELXL97
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      193(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measurement_device_type  'Enraf--Nonius CAD-4'
_diffrn_measurement_method       ω--2θ
_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  0.0202
_diffrn_reflns_av_sigmaI/netI    0.0432
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       0
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            2451
_diffrn_reflns_theta_full        25.07
_diffrn_reflns_theta_max         25.07
_diffrn_reflns_theta_min         2.01
_diffrn_standards_decay_%        1
_diffrn_standards_interval_count 200
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    3.185
_exptl_absorpt_correction_T_max  0.601
_exptl_absorpt_correction_T_min  0.417
_exptl_absorpt_correction_type   psi-scan
_exptl_absorpt_process_details   '(North et al.,  1968)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.674
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       irregular
_exptl_crystal_F_000             328
_exptl_crystal_size_max          0.43
_exptl_crystal_size_mid          0.26
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.321
_refine_diff_density_min         -0.386
_refine_ls_extinction_coef       0.024(2)
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     SHELXL97
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     177
_refine_ls_number_reflns         2312
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.064
_refine_ls_R_factor_all          0.0651
_refine_ls_R_factor_gt           0.0302
_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)+(0.0298P)²+0.241P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0657
_refine_ls_wR_factor_ref         0.0733
_reflns_number_gt                1724
_reflns_number_total             2312
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bt6779.cif
_cod_data_source_block           I
_cod_database_code               2207453
_cod_database_fobs_code          2207453
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
loop_
_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_type_symbol
Br1 0.34283(6) 0.31376(4) 0.41694(4) 0.05807(17) Uani d . 1 Br
C1 0.2699(4) 0.1119(3) 0.4304(3) 0.0383(7) Uani d . 1 C
C2 0.1930(4) 0.0140(4) 0.3160(3) 0.0447(8) Uani d . 1 C
H2 0.1800 0.0478 0.2343 0.054 Uiso calc R 1 H
C3 0.1358(5) -0.1333(4) 0.3235(3) 0.0471(8) Uani d . 1 C
H3 0.0803 -0.1987 0.2470 0.057 Uiso calc R 1 H
C4 0.1611(5) -0.1837(4) 0.4445(3) 0.0466(8) Uani d . 1 C
H4 0.1226 -0.2833 0.4494 0.056 Uiso calc R 1 H
C5 0.2431(4) -0.0873(3) 0.5584(3) 0.0402(7) Uani d . 1 C
H5 0.2629 -0.1229 0.6394 0.048 Uiso calc R 1 H
C6 0.2961(4) 0.0616(3) 0.5532(3) 0.0340(6) Uani d . 1 C
N7 0.3804(4) 0.1631(3) 0.6675(2) 0.0364(6) Uani d . 1 N
H7 0.443(4) 0.243(3) 0.655(3) 0.042(9) Uiso d . 1 H
C8 0.3823(4) 0.1389(3) 0.7906(3) 0.0354(7) Uani d . 1 C
H8 0.3056 0.0517 0.8032 0.042 Uiso calc R 1 H
C9 0.4871(4) 0.2306(3) 0.9005(3) 0.0349(6) Uani d . 1 C
C10 0.6149(4) 0.3665(3) 0.8919(3) 0.0391(7) Uani d . 1 C
O10 0.6240(3) 0.4202(2) 0.7910(2) 0.0518(6) Uani d . 1 O
O11 0.7285(3) 0.4408(2) 1.0075(2) 0.0449(5) Uani d . 1 O
C12 0.7771(4) 0.3556(3) 1.1131(3) 0.0421(7) Uani d . 1 C
O13 0.5985(3) 0.2662(2) 1.13445(19) 0.0459(5) Uani d . 1 O
C14 0.4647(4) 0.1877(3) 1.0279(3) 0.0393(7) Uani d . 1 C
O14 0.3378(3) 0.0921(2) 1.0466(2) 0.0552(6) Uani d . 1 O
C121 0.8572(5) 0.4650(4) 1.2359(3) 0.0597(9) Uani d . 1 C
H12A 0.9771 0.5273 1.2268 0.089 Uiso calc R 1 H
H12B 0.8860 0.4135 1.3107 0.089 Uiso calc R 1 H
H12C 0.7597 0.5240 1.2485 0.089 Uiso calc R 1 H
C122 0.9209(5) 0.2603(3) 1.0826(3) 0.0526(8) Uani d . 1 C
H12D 1.0389 0.3208 1.0686 0.079 Uiso calc R 1 H
H12E 0.8601 0.1924 1.0044 0.079 Uiso calc R 1 H
H12F 0.9556 0.2067 1.1551 0.079 Uiso calc R 1 H
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'
Br Br -0.2901 2.4595 '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
C2 C1 C6 120.5(3)
C2 C1 Br1 118.9(2)
C6 C1 Br1 120.6(2)
C3 C2 C1 119.9(3)
C3 C2 H2 120.0
C1 C2 H2 120.0
C2 C3 C4 119.9(3)
C2 C3 H3 120.1
C4 C3 H3 120.1
C3 C4 C5 120.4(3)
C3 C4 H4 119.8
C5 C4 H4 119.8
C4 C5 C6 120.5(3)
C4 C5 H5 119.7
C6 C5 H5 119.7
C5 C6 C1 118.7(3)
C5 C6 N7 122.0(3)
C1 C6 N7 119.2(3)
C8 N7 C6 126.4(3)
C8 N7 H7 118(2)
C6 N7 H7 115(2)
N7 C8 C9 125.7(3)
N7 C8 H8 117.2
C9 C8 H8 117.2
C8 C9 C10 121.6(3)
C8 C9 C14 117.8(2)
C10 C9 C14 120.6(3)
O10 C10 O11 118.5(3)
O10 C10 C9 125.2(3)
O11 C10 C9 116.3(2)
C10 O11 C12 116.9(2)
O11 C12 O13 110.3(2)
O11 C12 C122 110.4(3)
O13 C12 C122 110.2(2)
O11 C12 C121 106.0(2)
O13 C12 C121 106.2(3)
C122 C12 C121 113.7(3)
C14 O13 C12 118.6(2)
O14 C14 O13 118.3(3)
O14 C14 C9 125.8(3)
O13 C14 C9 115.9(2)
C12 C121 H12A 109.5
C12 C121 H12B 109.5
H12A C121 H12B 109.5
C12 C121 H12C 109.5
H12A C121 H12C 109.5
H12B C121 H12C 109.5
C12 C122 H12D 109.5
C12 C122 H12E 109.5
H12D C122 H12E 109.5
C12 C122 H12F 109.5
H12D C122 H12F 109.5
H12E C122 H12F 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C1 1.888(3)
C1 C2 1.386(4)
C1 C6 1.394(4)
C2 C3 1.375(4)
C2 H2 0.9300
C3 C4 1.378(4)
C3 H3 0.9300
C4 C5 1.380(4)
C4 H4 0.9300
C5 C6 1.383(4)
C5 H5 0.9300
C6 N7 1.409(4)
N7 C8 1.322(4)
N7 H7 0.83(3)
C8 C9 1.362(4)
C8 H8 0.9300
C9 C10 1.441(4)
C9 C14 1.452(4)
C10 O10 1.215(3)
C10 O11 1.359(4)
O11 C12 1.439(3)
C12 O13 1.444(4)
C12 C122 1.499(5)
C12 C121 1.507(4)
O13 C14 1.362(3)
C14 O14 1.203(3)
C121 H12A 0.9600
C121 H12B 0.9600
C121 H12C 0.9600
C122 H12D 0.9600
C122 H12E 0.9600
C122 H12F 0.9600
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
N7 H7 O10 . 0.83(3) 2.12(3) 2.734(3) 130(3)
C2 H2 O14 1_554 0.93 2.46 3.266(4) 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
C6 C1 C2 C3 2.1(4)
Br1 C1 C2 C3 -179.0(2)
C1 C2 C3 C4 -2.0(5)
C2 C3 C4 C5 0.1(5)
C3 C4 C5 C6 1.8(5)
C4 C5 C6 C1 -1.7(4)
C4 C5 C6 N7 -179.9(3)
C2 C1 C6 C5 -0.3(4)
Br1 C1 C6 C5 -179.2(2)
C2 C1 C6 N7 178.0(3)
Br1 C1 C6 N7 -0.8(4)
C5 C6 N7 C8 -14.8(4)
C1 C6 N7 C8 167.0(3)
C6 N7 C8 C9 170.5(3)
N7 C8 C9 C10 -1.7(5)
N7 C8 C9 C14 177.8(3)
C8 C9 C10 O10 9.2(5)
C14 C9 C10 O10 -170.3(3)
C8 C9 C10 O11 -173.0(3)
C14 C9 C10 O11 7.5(4)
O10 C10 O11 C12 -156.2(3)
C9 C10 O11 C12 25.8(4)
C10 O11 C12 O13 -52.0(3)
C10 O11 C12 C122 70.0(3)
C10 O11 C12 C121 -166.5(3)
O11 C12 O13 C14 46.9(3)
C122 C12 O13 C14 -75.2(3)
C121 C12 O13 C14 161.2(2)
C12 O13 C14 O14 165.4(3)
C12 O13 C14 C9 -15.9(4)
C8 C9 C14 O14 -13.5(5)
C10 C9 C14 O14 166.0(3)
C8 C9 C14 O13 168.0(3)
C10 C9 C14 O13 -12.5(4)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 12584640
