#------------------------------------------------------------------------------
#$Date: 2017-10-13 12:31:46 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201979 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/23/48/2234858.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_2234858
loop_
_publ_author_name
'Li, Guang-Bing'
'Li, Lu'
'Wang, Guo-Xi'
_publ_section_title
;
 (E)-1-(5-Bromo-2-hydroxyphenyl)-3-[4-(dimethylamino)phenyl]prop-2-en-1-one
;
_journal_coeditor_code           XU5515
_journal_issue                   5
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1446
_journal_paper_doi               10.1107/S1600536812016327
_journal_volume                  68
_journal_year                    2012
_chemical_formula_iupac          'C17 H16 Br N O2'
_chemical_formula_moiety         'C17 H16 Br N O2'
_chemical_formula_sum            'C17 H16 Br N O2'
_chemical_formula_weight         346.22
_chemical_name_systematic
;
(E)-1-(5-Bromo-2-hydroxyphenyl)-3-[4-(dimethylamino)phenyl]prop-
2-en-1-one
;
_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                 106.00(2)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   15.1905(5)
_cell_length_b                   5.4501(2)
_cell_length_c                   19.7569(9)
_cell_measurement_reflns_used    2736
_cell_measurement_temperature    123(2)
_cell_measurement_theta_max      27.48
_cell_measurement_theta_min      2.21
_cell_volume                     1572.31(19)
_computing_cell_refinement       'CrystalClear (Rigaku, 2005)'
_computing_data_collection       'CrystalClear (Rigaku, 2005)'
_computing_data_reduction        'CrystalClear (Rigaku, 2005)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      123(2)
_diffrn_detector_area_resol_mean 13.6612
_diffrn_measured_fraction_theta_full 0.986
_diffrn_measured_fraction_theta_max 0.986
_diffrn_measurement_device_type  'Rigaku Mercury2'
_diffrn_measurement_method       'CCD profile fitting'
_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  0.0747
_diffrn_reflns_av_sigmaI/netI    0.0977
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -18
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            8044
_diffrn_reflns_theta_full        25.00
_diffrn_reflns_theta_max         25.00
_diffrn_reflns_theta_min         2.21
_exptl_absorpt_coefficient_mu    2.618
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.910
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(CrystalClear; Rigaku, 2005)'
_exptl_crystal_colour            red
_exptl_crystal_density_diffrn    1.463
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.05
_exptl_crystal_size_min          0.05
_refine_diff_density_max         1.578
_refine_diff_density_min         -1.112
_refine_ls_extinction_coef       0.002
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc²λ³/sin(2θ)]^-1/4^
_refine_ls_extinction_method     'SHELXTL (Sheldrick, 2008)'
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         2736
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.093
_refine_ls_R_factor_all          0.1294
_refine_ls_R_factor_gt           0.0889
_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)+(0.1410P)²+0.6743P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2483
_refine_ls_wR_factor_ref         0.2866
_reflns_number_gt                1538
_reflns_number_total             2736
_reflns_threshold_expression     I>2sigma(I)
_cod_data_source_file            xu5515.cif
_cod_data_source_block           I
_cod_original_cell_volume        1572.34(11)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               2234858
_cod_database_fobs_code          2234858
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 1.08032(7) -0.2556(2) 0.57680(7) 0.1050(7) Uani d . 1 1
O O1 0.6988(3) 0.0521(10) 0.6480(2) 0.0469(13) Uani d . 1 1
C C7 0.7599(4) 0.0665(12) 0.6153(3) 0.0329(15) Uani d . 1 1
N N1 0.5880(3) 1.1541(11) 0.3308(3) 0.0355(14) Uani d . 1 1
O O2 0.7796(4) -0.3021(10) 0.7239(3) 0.0600(16) Uani d D 1 1
H H2 0.7357 -0.2242 0.7002 0.090 Uiso d RD 1 1
C C10 0.6627(4) 0.6074(12) 0.4911(3) 0.0307(14) Uani d . 1 1
C C9 0.6821(4) 0.4141(13) 0.5444(3) 0.0331(15) Uani d . 1 1
H H9A 0.6394 0.3991 0.5714 0.040 Uiso calc R 1 1
C C14 0.5541(4) 0.9164(12) 0.4255(3) 0.0339(15) Uani d . 1 1
H H14A 0.4969 0.9979 0.4183 0.041 Uiso calc R 1 1
C C13 0.6124(4) 0.9790(12) 0.3830(3) 0.0331(15) Uani d . 1 1
C C5 0.8429(5) -0.2911(12) 0.6878(4) 0.0386(17) Uani d . 1 1
C C12 0.6988(4) 0.8490(12) 0.3966(3) 0.0362(16) Uani d . 1 1
H H12A 0.7404 0.8867 0.3699 0.043 Uiso calc R 1 1
C C1 0.9105(4) -0.1047(14) 0.6015(3) 0.0412(17) Uani d . 1 1
H H1A 0.9106 0.0160 0.5669 0.049 Uiso calc R 1 1
C C6 0.8391(4) -0.1080(12) 0.6344(3) 0.0307(14) Uani d . 1 1
C C2 0.9802(5) -0.2758(13) 0.6193(4) 0.0446(19) Uani d . 1 1
C C15 0.5789(5) 0.7398(12) 0.4769(4) 0.0342(16) Uani d . 1 1
H H15A 0.5380 0.7044 0.5043 0.041 Uiso calc R 1 1
C C11 0.7207(4) 0.6699(12) 0.4483(3) 0.0364(16) Uani d . 1 1
H H11A 0.7772 0.5849 0.4555 0.044 Uiso calc R 1 1
C C4 0.9150(5) -0.4652(14) 0.7037(4) 0.0483(19) Uani d . 1 1
H H4A 0.9168 -0.5864 0.7387 0.058 Uiso calc R 1 1
C C8 0.7530(4) 0.2529(11) 0.5605(3) 0.0294(15) Uani d . 1 1
H H8A 0.7987 0.2610 0.5360 0.035 Uiso calc R 1 1
C C16 0.5060(5) 1.3053(13) 0.3242(4) 0.0429(18) Uani d . 1 1
H H16A 0.4515 1.2004 0.3123 0.064 Uiso calc R 1 1
H H16B 0.5012 1.4277 0.2871 0.064 Uiso calc R 1 1
H H16C 0.5105 1.3887 0.3690 0.064 Uiso calc R 1 1
C C3 0.9833(4) -0.4609(14) 0.6688(4) 0.0438(18) Uani d . 1 1
H H3A 1.0306 -0.5806 0.6784 0.053 Uiso calc R 1 1
C C17 0.6536(6) 1.2333(13) 0.2900(4) 0.0441(18) Uani d . 1 1
H H17A 0.6841 1.0888 0.2775 0.066 Uiso calc R 1 1
H H17B 0.6994 1.3444 0.3190 0.066 Uiso calc R 1 1
H H17C 0.6197 1.3183 0.2470 0.066 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'
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
O1 C7 C8 120.3(6)
O1 C7 C6 118.8(6)
C8 C7 C6 120.9(5)
C13 N1 C16 120.0(5)
C13 N1 C17 121.2(5)
C16 N1 C17 117.5(6)
C5 O2 H2 105.1
C11 C10 C15 115.4(6)
C11 C10 C9 124.6(6)
C15 C10 C9 120.0(6)
C8 C9 C10 128.6(6)
C8 C9 H9A 115.7
C10 C9 H9A 115.7
C15 C14 C13 121.1(6)
C15 C14 H14A 119.5
C13 C14 H14A 119.5
N1 C13 C14 121.7(6)
N1 C13 C12 121.2(5)
C14 C13 C12 117.0(6)
O2 C5 C4 118.2(6)
O2 C5 C6 121.8(6)
C4 C5 C6 119.9(7)
C11 C12 C13 120.1(6)
C11 C12 H12A 119.9
C13 C12 H12A 119.9
C2 C1 C6 120.5(6)
C2 C1 H1A 119.8
C6 C1 H1A 119.8
C1 C6 C5 117.7(6)
C1 C6 C7 122.8(6)
C5 C6 C7 119.4(6)
C1 C2 C3 122.8(7)
C1 C2 Br1 119.4(6)
C3 C2 Br1 117.8(5)
C14 C15 C10 123.3(6)
C14 C15 H15A 118.3
C10 C15 H15A 118.3
C12 C11 C10 123.1(6)
C12 C11 H11A 118.5
C10 C11 H11A 118.5
C3 C4 C5 120.9(7)
C3 C4 H4A 119.6
C5 C4 H4A 119.6
C9 C8 C7 120.7(6)
C9 C8 H8A 119.7
C7 C8 H8A 119.7
N1 C16 H16A 109.5
N1 C16 H16B 109.5
H16A C16 H16B 109.5
N1 C16 H16C 109.5
H16A C16 H16C 109.5
H16B C16 H16C 109.5
C2 C3 C4 118.1(6)
C2 C3 H3A 120.9
C4 C3 H3A 120.9
N1 C17 H17A 109.5
N1 C17 H17B 109.5
H17A C17 H17B 109.5
N1 C17 H17C 109.5
H17A C17 H17C 109.5
H17B C17 H17C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C2 1.933(8)
O1 C7 1.271(7)
C7 C8 1.468(9)
C7 C6 1.499(9)
N1 C13 1.380(8)
N1 C16 1.469(8)
N1 C17 1.506(9)
O2 C5 1.347(9)
O2 H2 0.8200
C10 C11 1.421(9)
C10 C15 1.423(9)
C10 C9 1.461(9)
C9 C8 1.358(9)
C9 H9A 0.9500
C14 C15 1.374(9)
C14 C13 1.419(8)
C14 H14A 0.9500
C13 C12 1.450(9)
C5 C4 1.417(10)
C5 C6 1.441(9)
C12 C11 1.386(9)
C12 H12A 0.9500
C1 C2 1.382(9)
C1 C6 1.409(9)
C1 H1A 0.9500
C2 C3 1.396(10)
C15 H15A 0.9500
C11 H11A 0.9500
C4 C3 1.397(9)
C4 H4A 0.9500
C8 H8A 0.9500
C16 H16A 0.9800
C16 H16B 0.9800
C16 H16C 0.9800
C3 H3A 0.9500
C17 H17A 0.9800
C17 H17B 0.9800
C17 H17C 0.9800
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
O2 H2 O1 . 0.82 1.82 2.543(7) 146
C17 H17A O2 4_565 0.98 2.55 3.503(10) 164
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 13002432
