#------------------------------------------------------------------------------
#$Date: 2016-02-21 02:03:34 +0200 (Sun, 21 Feb 2016) $
#$Revision: 176798 $
#$URL: svn://www.crystallography.net/cod/cif/2/23/86/2238676.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_2238676
loop_
_publ_author_name
'Fatima, Zeenat'
'Rambabu, Gottimukkala'
'Reddy, Bandapalli Palakshi'
'Vijayakumar, Vijayaparthasarathi'
'Velmurugan, Devadasan'
_publ_section_title
;
 N-(4-Bromophenyl)-2,6-dimethyl-1,3-dioxan-4-amine
;
_journal_coeditor_code           SU2646
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1579
_journal_paper_doi               10.1107/S1600536813025750
_journal_volume                  69
_journal_year                    2013
_chemical_formula_iupac          'C12 H16 Br N O2'
_chemical_formula_moiety         'C12 H16 Br N O2'
_chemical_formula_sum            'C12 H16 Br N O2'
_chemical_formula_weight         286.17
_chemical_name_systematic
;
N-(4-Bromophenyl)-2,6-dimethyl-1,3-dioxan-4-amine
;
_space_group_IT_number           14
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 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                 115.543(3)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   9.9367(5)
_cell_length_b                   13.5660(6)
_cell_length_c                   10.3206(5)
_cell_measurement_reflns_used    3119
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      28.35
_cell_measurement_theta_min      2.27
_cell_volume                     1255.25(11)
_computing_cell_refinement       'SAINT (Bruker, 2008)'
_computing_data_collection       'APEX2 (Bruker, 2008)'
_computing_data_reduction        'SAINT (Bruker, 2008)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material
'SHELXL97 (Sheldrick, 2008) and PLATON (Spek, 2009)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.997
_diffrn_measurement_device_type
'Bruker SMART APEXII area-detector diffractometer'
_diffrn_measurement_method       'ω and φ 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  0.0324
_diffrn_reflns_av_sigmaI/netI    0.0404
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            11981
_diffrn_reflns_theta_full        28.35
_diffrn_reflns_theta_max         28.35
_diffrn_reflns_theta_min         2.27
_exptl_absorpt_coefficient_mu    3.261
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.3101
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2008)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.514
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             584
_exptl_crystal_size_max          0.25
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.449
_refine_diff_density_min         -0.380
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.013
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     150
_refine_ls_number_reflns         3119
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.014
_refine_ls_R_factor_all          0.0853
_refine_ls_R_factor_gt           0.0366
_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)+(0.0432P)²+0.0602P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0794
_refine_ls_wR_factor_ref         0.0917
_reflns_number_gt                1819
_reflns_number_total             3119
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            su2646.cif
_cod_data_source_block           I
_cod_original_cell_volume        1255.25(10)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2238676
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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_symmetry_multiplicity
Br Br1 1.07805(3) 0.63232(2) 1.22087(3) 0.07742(15) Uani d . 1 1
O O1 0.70096(17) 0.52265(9) 0.47016(15) 0.0474(4) Uani d . 1 1
O O2 0.61959(17) 0.53559(10) 0.22317(15) 0.0488(4) Uani d . 1 1
N N1 0.6108(2) 0.62162(13) 0.6010(2) 0.0502(5) Uani d D 1 1
H H1 0.531(2) 0.5954(17) 0.588(3) 0.060 Uiso d D 1 1
C C1 0.4240(3) 0.64080(17) 0.0718(3) 0.0640(7) Uani d . 1 1
H H1A 0.4566 0.6270 -0.0014 0.096 Uiso calc R 1 1
H H1B 0.3852 0.7067 0.0598 0.096 Uiso calc R 1 1
H H1C 0.3475 0.5949 0.0642 0.096 Uiso calc R 1 1
C C2 0.5537(3) 0.63121(15) 0.2171(2) 0.0497(6) Uani d . 1 1
H H2 0.6276 0.6818 0.2260 0.060 Uiso calc R 1 1
C C3 0.5121(3) 0.64209(15) 0.3411(3) 0.0504(6) Uani d . 1 1
H H3A 0.4781 0.7088 0.3433 0.060 Uiso calc R 1 1
H H3B 0.4311 0.5973 0.3282 0.060 Uiso calc R 1 1
C C4 0.6445(3) 0.61968(14) 0.4810(2) 0.0461(5) Uani d . 1 1
H H4 0.7225 0.6685 0.4960 0.055 Uiso calc R 1 1
C C5 0.7436(3) 0.51969(17) 0.3564(2) 0.0522(6) Uani d . 1 1
H H5 0.8196 0.5701 0.3714 0.063 Uiso calc R 1 1
C C6 0.8065(3) 0.4193(2) 0.3537(3) 0.0756(8) Uani d . 1 1
H H6A 0.8360 0.4162 0.2766 0.113 Uiso calc R 1 1
H H6B 0.7320 0.3701 0.3394 0.113 Uiso calc R 1 1
H H6C 0.8917 0.4075 0.4432 0.113 Uiso calc R 1 1
C C7 0.7211(3) 0.62384(13) 0.7422(2) 0.0433(5) Uani d . 1 1
C C8 0.6828(3) 0.60493(15) 0.8537(3) 0.0501(6) Uani d . 1 1
H H8 0.5844 0.5896 0.8328 0.060 Uiso calc R 1 1
C C9 0.7872(3) 0.60831(15) 0.9954(3) 0.0545(6) Uani d . 1 1
H H9 0.7594 0.5944 1.0687 0.065 Uiso calc R 1 1
C C10 0.9320(3) 0.63231(14) 1.0272(3) 0.0504(6) Uani d . 1 1
C C11 0.9719(3) 0.65323(19) 0.9185(3) 0.0622(7) Uani d . 1 1
H H11 1.0698 0.6707 0.9402 0.075 Uiso calc R 1 1
C C12 0.8674(3) 0.64851(18) 0.7771(3) 0.0586(6) Uani d . 1 1
H H12 0.8960 0.6622 0.7042 0.070 Uiso calc R 1 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
C5 O1 C4 110.76(15)
C5 O2 C2 111.66(16)
C7 N1 C4 122.5(2)
C7 N1 H1 116.7(18)
C4 N1 H1 114.8(18)
C2 C1 H1A 109.5
C2 C1 H1B 109.5
H1A C1 H1B 109.5
C2 C1 H1C 109.5
H1A C1 H1C 109.5
H1B C1 H1C 109.5
O2 C2 C1 107.42(17)
O2 C2 C3 109.59(17)
C1 C2 C3 114.0(2)
O2 C2 H2 108.6
C1 C2 H2 108.6
C3 C2 H2 108.6
C4 C3 C2 110.3(2)
C4 C3 H3A 109.6
C2 C3 H3A 109.6
C4 C3 H3B 109.6
C2 C3 H3B 109.6
H3A C3 H3B 108.1
N1 C4 O1 109.21(16)
N1 C4 C3 113.3(2)
O1 C4 C3 108.37(17)
N1 C4 H4 108.6
O1 C4 H4 108.6
C3 C4 H4 108.6
O1 C5 O2 110.92(17)
O1 C5 C6 108.55(19)
O2 C5 C6 108.37(19)
O1 C5 H5 109.7
O2 C5 H5 109.7
C6 C5 H5 109.7
C5 C6 H6A 109.5
C5 C6 H6B 109.5
H6A C6 H6B 109.5
C5 C6 H6C 109.5
H6A C6 H6C 109.5
H6B C6 H6C 109.5
C12 C7 C8 117.7(2)
C12 C7 N1 122.8(2)
C8 C7 N1 119.4(2)
C9 C8 C7 121.6(2)
C9 C8 H8 119.2
C7 C8 H8 119.2
C10 C9 C8 119.6(2)
C10 C9 H9 120.2
C8 C9 H9 120.2
C9 C10 C11 119.9(2)
C9 C10 Br1 119.97(18)
C11 C10 Br1 120.13(19)
C10 C11 C12 120.3(2)
C10 C11 H11 119.9
C12 C11 H11 119.9
C7 C12 C11 121.0(2)
C7 C12 H12 119.5
C11 C12 H12 119.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C10 1.898(2)
O1 C5 1.410(2)
O1 C4 1.454(2)
O2 C5 1.412(3)
O2 C2 1.442(2)
N1 C7 1.396(3)
N1 C4 1.416(3)
N1 H1 0.824(16)
C1 C2 1.503(3)
C1 H1A 0.9600
C1 H1B 0.9600
C1 H1C 0.9600
C2 C3 1.513(3)
C2 H2 0.9800
C3 C4 1.507(3)
C3 H3A 0.9700
C3 H3B 0.9700
C4 H4 0.9800
C5 C6 1.504(3)
C5 H5 0.9800
C6 H6A 0.9600
C6 H6B 0.9600
C6 H6C 0.9600
C7 C12 1.379(3)
C7 C8 1.383(3)
C8 C9 1.382(3)
C8 H8 0.9300
C9 C10 1.369(4)
C9 H9 0.9300
C10 C11 1.371(3)
C11 C12 1.381(4)
C11 H11 0.9300
C12 H12 0.9300
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
N1 H1 O1 3_666 0.824(16) 2.655(16) 3.465(2) 168(2)
C8 H8 O2 3_666 0.93 2.51 3.352(3) 150
C9 H9 O2 1_556 0.93 2.65 3.557(3) 165
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
C5 O2 C2 C1 179.79(18)
C5 O2 C2 C3 -55.9(2)
O2 C2 C3 C4 53.0(2)
C1 C2 C3 C4 173.36(17)
C7 N1 C4 O1 73.0(2)
C7 N1 C4 C3 -166.05(17)
C5 O1 C4 N1 -176.72(18)
C5 O1 C4 C3 59.4(2)
C2 C3 C4 N1 -175.78(17)
C2 C3 C4 O1 -54.4(2)
C4 O1 C5 O2 -63.2(2)
C4 O1 C5 C6 177.81(19)
C2 O2 C5 O1 61.5(2)
C2 O2 C5 C6 -179.48(18)
C4 N1 C7 C12 16.4(3)
C4 N1 C7 C8 -166.52(18)
C12 C7 C8 C9 -1.4(3)
N1 C7 C8 C9 -178.59(18)
C7 C8 C9 C10 1.0(3)
C8 C9 C10 C11 0.3(3)
C8 C9 C10 Br1 -177.60(15)
C9 C10 C11 C12 -1.1(4)
Br1 C10 C11 C12 176.77(18)
C8 C7 C12 C11 0.6(3)
N1 C7 C12 C11 177.6(2)
C10 C11 C12 C7 0.7(4)
