#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/68/2226887.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_2226887
loop_
_publ_author_name
'Haridharan, N.'
'Ramkumar, V.'
'Dhamodharan, R.'
_publ_section_title
;
 2-Bromo-2-methyl-N-(4-methyl-2-oxo-2H-chromen-7-yl)propanamide
;
_journal_coeditor_code           HB5522
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o2007
_journal_paper_doi               10.1107/S1600536810026802
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C14 H14 Br N O3'
_chemical_formula_moiety         'C14 H14 Br N O3'
_chemical_formula_sum            'C14 H14 Br N O3'
_chemical_formula_weight         324.17
_chemical_name_systematic
;
2-Bromo-2-methyl-N-(4-methyl-2-oxo-2H-chromen-7-yl)propanamide
;
_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                105.255(5)
_cell_angle_beta                 100.630(5)
_cell_angle_gamma                93.572(5)
_cell_formula_units_Z            2
_cell_length_a                   6.7054(8)
_cell_length_b                   9.2415(11)
_cell_length_c                   11.7612(15)
_cell_measurement_reflns_used    1785
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      24.53
_cell_measurement_theta_min      2.509
_cell_volume                     686.33(15)
_computing_cell_refinement       'SAINT-Plus (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT-Plus (Bruker, 2004)'
_computing_molecular_graphics    'ORTEP-3 (Farrugia, 1997)'
_computing_publication_material  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.861
_diffrn_measured_fraction_theta_max 0.736
_diffrn_measurement_device_type  'Bruker APEXII CCD'
_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  0.0198
_diffrn_reflns_av_sigmaI/netI    0.0385
_diffrn_reflns_limit_h_max       5
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -11
_diffrn_reflns_number            4624
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         28.27
_diffrn_reflns_theta_min         1.84
_exptl_absorpt_coefficient_mu    2.998
_exptl_absorpt_correction_T_max  0.662
_exptl_absorpt_correction_T_min  0.366
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2004)'
_exptl_crystal_colour            light-yellow
_exptl_crystal_density_diffrn    1.569
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       slab
_exptl_crystal_F_000             328
_exptl_crystal_size_max          0.42
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.15
_refine_diff_density_max         1.157
_refine_diff_density_min         -0.526
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.093
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     179
_refine_ls_number_reflns         2511
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.093
_refine_ls_R_factor_all          0.0874
_refine_ls_R_factor_gt           0.0574
_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)+(0.1000P)²+0.3500P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1545
_refine_ls_wR_factor_ref         0.1737
_reflns_number_gt                1716
_reflns_number_total             2511
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            hb5522.cif
_cod_data_source_block           I
_cod_database_code               2226887
_cod_database_fobs_code          2226887
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, -y, -z'
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
Br Br1 0.34908(9) 0.90419(7) 0.61854(6) 0.0714(3) Uani d . 1 . .
C C1 0.2652(7) 0.2486(5) 1.0477(4) 0.0377(11) Uani d . 1 . .
C C2 0.3283(7) 0.3307(5) 1.1731(4) 0.0388(11) Uani d . 1 . .
H H2 0.3551 0.2772 1.2299 0.047 Uiso calc R 1 . .
C C3 0.3497(6) 0.4824(5) 1.2107(4) 0.0352(10) Uani d . 1 . .
C C4 0.3086(6) 0.5641(5) 1.1221(4) 0.0291(10) Uani d . 1 . .
C C5 0.3260(7) 0.7225(5) 1.1480(4) 0.0362(11) Uani d . 1 . .
H H5 0.3639 0.7807 1.2279 0.043 Uiso calc R 1 . .
C C6 0.2890(7) 0.7927(5) 1.0596(4) 0.0347(10) Uani d . 1 . .
H H6 0.3042 0.8976 1.0795 0.042 Uiso calc R 1 . .
C C7 0.2285(6) 0.7087(5) 0.9391(4) 0.0291(9) Uani d . 1 . .
C C8 0.2092(6) 0.5511(4) 0.9098(4) 0.0282(9) Uani d . 1 . .
H H8 0.1700 0.4926 0.8301 0.034 Uiso calc R 1 . .
C C9 0.2497(6) 0.4850(4) 1.0021(4) 0.0267(9) Uani d . 1 . .
C C10 0.4152(10) 0.5641(7) 1.3424(5) 0.0616(15) Uani d . 1 . .
H H10A 0.3063 0.6170 1.3694 0.092 Uiso calc R 1 . .
H H10B 0.5336 0.6349 1.3549 0.092 Uiso calc R 1 . .
H H10C 0.4477 0.4925 1.3872 0.092 Uiso calc R 1 . .
C C11 0.1328(7) 0.7309(5) 0.7300(4) 0.0394(11) Uani d . 1 . .
C C12 0.0809(8) 0.8434(6) 0.6573(4) 0.0464(12) Uani d . 1 . .
C C13 -0.0004(12) 0.9843(7) 0.7192(6) 0.0723(18) Uani d . 1 . .
H H13A -0.1170 0.9573 0.7491 0.108 Uiso calc R 1 . .
H H13B -0.0397 1.0413 0.6629 0.108 Uiso calc R 1 . .
H H13C 0.1037 1.0443 0.7851 0.108 Uiso calc R 1 . .
C C14 -0.0590(10) 0.7627(8) 0.5376(5) 0.0688(17) Uani d . 1 . .
H H14A -0.1897 0.7310 0.5509 0.103 Uiso calc R 1 . .
H H14B -0.0003 0.6760 0.4984 0.103 Uiso calc R 1 . .
H H14C -0.0757 0.8300 0.4876 0.103 Uiso calc R 1 . .
N N1 0.1878(5) 0.7900(4) 0.8526(3) 0.0344(9) Uani d D 1 . .
O O1 0.2284(4) 0.3286(3) 0.9663(3) 0.0340(7) Uani d . 1 . .
O O2 0.2428(6) 0.1122(4) 1.0081(3) 0.0560(10) Uani d . 1 . .
O O3 0.1211(7) 0.5975(4) 0.6804(3) 0.0650(12) Uani d . 1 . .
H H1N 0.196(7) 0.891(3) 0.889(4) 0.048(14) Uiso d D 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'
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O2 C1 O1 . . 116.6(4) ?
O2 C1 C2 . . 125.3(4) ?
O1 C1 C2 . . 118.1(4) ?
C3 C2 C1 . . 122.1(4) ?
C3 C2 H2 . . 119.0 ?
C1 C2 H2 . . 119.0 ?
C2 C3 C4 . . 118.5(4) ?
C2 C3 C10 . . 120.5(4) ?
C4 C3 C10 . . 121.0(4) ?
C9 C4 C5 . . 116.0(4) ?
C9 C4 C3 . . 119.2(4) ?
C5 C4 C3 . . 124.8(4) ?
C6 C5 C4 . . 121.8(4) ?
C6 C5 H5 . . 119.1 ?
C4 C5 H5 . . 119.1 ?
C5 C6 C7 . . 120.5(4) ?
C5 C6 H6 . . 119.7 ?
C7 C6 H6 . . 119.7 ?
C6 C7 C8 . . 119.3(4) ?
C6 C7 N1 . . 117.1(4) ?
C8 C7 N1 . . 123.5(4) ?
C9 C8 C7 . . 118.1(4) ?
C9 C8 H8 . . 120.9 ?
C7 C8 H8 . . 120.9 ?
C8 C9 C4 . . 124.2(4) ?
C8 C9 O1 . . 114.9(3) ?
C4 C9 O1 . . 120.9(4) ?
C3 C10 H10A . . 109.5 ?
C3 C10 H10B . . 109.5 ?
H10A C10 H10B . . 109.5 ?
C3 C10 H10C . . 109.5 ?
H10A C10 H10C . . 109.5 ?
H10B C10 H10C . . 109.5 ?
O3 C11 N1 . . 123.0(4) ?
O3 C11 C12 . . 120.7(4) ?
N1 C11 C12 . . 116.2(4) ?
C13 C12 C14 . . 111.2(5) ?
C13 C12 C11 . . 116.9(4) ?
C14 C12 C11 . . 109.7(4) ?
C13 C12 Br1 . . 108.2(4) ?
C14 C12 Br1 . . 106.0(4) ?
C11 C12 Br1 . . 104.1(3) ?
C12 C13 H13A . . 109.5 ?
C12 C13 H13B . . 109.5 ?
H13A C13 H13B . . 109.5 ?
C12 C13 H13C . . 109.5 ?
H13A C13 H13C . . 109.5 ?
H13B C13 H13C . . 109.5 ?
C12 C14 H14A . . 109.5 ?
C12 C14 H14B . . 109.5 ?
H14A C14 H14B . . 109.5 ?
C12 C14 H14C . . 109.5 ?
H14A C14 H14C . . 109.5 ?
H14B C14 H14C . . 109.5 ?
C11 N1 C7 . . 126.8(4) ?
C11 N1 H1N . . 122(3) ?
C7 N1 H1N . . 111(3) ?
C1 O1 C9 . . 121.2(3) ?
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
Br1 C12 . 2.017(5) ?
C1 O2 . 1.213(5) ?
C1 O1 . 1.353(6) ?
C1 C2 . 1.439(7) ?
C2 C3 . 1.344(6) ?
C2 H2 . 0.9300 ?
C3 C4 . 1.438(7) ?
C3 C10 . 1.502(7) ?
C4 C9 . 1.377(6) ?
C4 C5 . 1.407(6) ?
C5 C6 . 1.358(7) ?
C5 H5 . 0.9300 ?
C6 C7 . 1.395(6) ?
C6 H6 . 0.9300 ?
C7 C8 . 1.397(6) ?
C7 N1 . 1.414(6) ?
C8 C9 . 1.373(6) ?
C8 H8 . 0.9300 ?
C9 O1 . 1.385(5) ?
C10 H10A . 0.9600 ?
C10 H10B . 0.9600 ?
C10 H10C . 0.9600 ?
C11 O3 . 1.208(6) ?
C11 N1 . 1.370(6) ?
C11 C12 . 1.529(7) ?
C12 C13 . 1.503(8) ?
C12 C14 . 1.514(7) ?
C13 H13A . 0.9600 ?
C13 H13B . 0.9600 ?
C13 H13C . 0.9600 ?
C14 H14A . 0.9600 ?
C14 H14B . 0.9600 ?
C14 H14C . 0.9600 ?
N1 H1N . 0.91(2) ?
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 H8 O3 . 0.93 2.21 2.804(6) 121
N1 H1N O2 1_565 0.91(2) 2.12(2) 3.016(5) 168(5)
C6 H6 O2 1_565 0.93 2.38 3.189(6) 145
C13 H13C O2 1_565 0.96 2.51 3.347(8) 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_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O2 C1 C2 C3 . . . . -179.9(5) ?
O1 C1 C2 C3 . . . . 0.5(6) ?
C1 C2 C3 C4 . . . . -0.2(6) ?
C1 C2 C3 C10 . . . . 179.8(4) ?
C2 C3 C4 C9 . . . . -0.3(6) ?
C10 C3 C4 C9 . . . . 179.7(4) ?
C2 C3 C4 C5 . . . . -179.5(4) ?
C10 C3 C4 C5 . . . . 0.5(7) ?
C9 C4 C5 C6 . . . . -0.7(6) ?
C3 C4 C5 C6 . . . . 178.6(4) ?
C4 C5 C6 C7 . . . . 1.1(7) ?
C5 C6 C7 C8 . . . . -1.0(6) ?
C5 C6 C7 N1 . . . . 178.4(4) ?
C6 C7 C8 C9 . . . . 0.5(6) ?
N1 C7 C8 C9 . . . . -178.9(4) ?
C7 C8 C9 C4 . . . . -0.1(6) ?
C7 C8 C9 O1 . . . . -179.7(3) ?
C5 C4 C9 C8 . . . . 0.2(6) ?
C3 C4 C9 C8 . . . . -179.1(4) ?
C5 C4 C9 O1 . . . . 179.8(3) ?
C3 C4 C9 O1 . . . . 0.5(6) ?
O3 C11 C12 C13 . . . . 150.9(6) ?
N1 C11 C12 C13 . . . . -27.8(7) ?
O3 C11 C12 C14 . . . . 23.1(7) ?
N1 C11 C12 C14 . . . . -155.6(5) ?
O3 C11 C12 Br1 . . . . -89.9(5) ?
N1 C11 C12 Br1 . . . . 91.4(4) ?
O3 C11 N1 C7 . . . . -3.3(7) ?
C12 C11 N1 C7 . . . . 175.3(4) ?
C6 C7 N1 C11 . . . . 177.9(4) ?
C8 C7 N1 C11 . . . . -2.8(6) ?
O2 C1 O1 C9 . . . . -180.0(4) ?
C2 C1 O1 C9 . . . . -0.3(6) ?
C8 C9 O1 C1 . . . . 179.4(4) ?
C4 C9 O1 C1 . . . . -0.2(5) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24745510
