#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/10/2211008.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_2211008
loop_
_publ_author_name
'P. S. Patil'
'Mohd Mustaqim Rosli'
'Hoong-Kun Fun'
'Ibrahim Abdul Razak '
'Vedavati G. Puranik'
'S. M. Dharmaprakash'
_publ_section_title
;
 3-(3-Bromophenyl)-1-(4-methoxyphenyl)prop-2-en-1-one
;
_journal_coeditor_code           GG2012
_journal_issue                   11
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o4798
_journal_page_last               o4799
_journal_paper_doi               10.1107/S1600536806039778
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C16 H13 Br O2'
_chemical_formula_moiety         'C16 H13 Br O2'
_chemical_formula_sum            'C16 H13 Br O2'
_chemical_formula_weight         317.17
_chemical_name_common
;
3-(3-Bromophenyl)-1-(4-meyhoxyphenyl)prop-2-en-1-one
;
_chemical_name_systematic
;
3-(3-Bromophenyl)-1-(4-meyhoxyphenyl)prop-2-en-1-one
;
_space_group_IT_number           4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  'P 2yb'
_symmetry_space_group_name_H-M   'P 1 21 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                 107.3130(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            2
_cell_length_a                   10.29170(10)
_cell_length_b                   3.89700(10)
_cell_length_c                   17.0919(2)
_cell_measurement_reflns_used    7113
_cell_measurement_temperature    100.0(10)
_cell_measurement_theta_max      37.50
_cell_measurement_theta_min      2.73
_cell_volume                     654.44(2)
_computing_cell_refinement       APEX2
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'SAINT (Bruker, 2005)'
_computing_molecular_graphics    SHELXTL
_computing_publication_material
;
SHELXTL, PARST (Nardelli, 1995) and PLATON (Spek, 2003)
;
_computing_structure_refinement  SHELXTL
_computing_structure_solution    'SHELXTL (Sheldrick, 1998)'
_diffrn_ambient_temperature      100.0(10)
_diffrn_detector_area_resol_mean 8.33
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_device_type
;
Bruker SMART APEX2 CCD area-detector
;
_diffrn_measurement_method       ω
_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  0.027
_diffrn_reflns_av_sigmaI/netI    0.039
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            31059
_diffrn_reflns_theta_full        37.50
_diffrn_reflns_theta_max         37.50
_diffrn_reflns_theta_min         1.25
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    3.135
_exptl_absorpt_correction_T_max  0.391
_exptl_absorpt_correction_T_min  0.369
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_crystal_colour            Yellow
_exptl_crystal_density_diffrn    1.610
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       Block
_exptl_crystal_F_000             320
_exptl_crystal_size_max          0.40
_exptl_crystal_size_mid          0.38
_exptl_crystal_size_min          0.37
_refine_diff_density_max         0.64
_refine_diff_density_min         -0.37
_refine_ls_abs_structure_details 'Flack (1983), 2981 Friedel pairs'
_refine_ls_abs_structure_Flack   0.008(5)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.083
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         6812
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.083
_refine_ls_R_factor_all          0.0289
_refine_ls_R_factor_gt           0.0235
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.001
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0342P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0568
_refine_ls_wR_factor_ref         0.0674
_reflns_number_gt                6194
_reflns_number_total             6812
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            gg2012.cif
_cod_data_source_block           I
_cod_depositor_comments
;
The following automatic conversions were performed:
'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to '/home/saulius/struct/CIF-dictionaries/cif_core.dic'
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_enum 1527 2010-12-29 10:47:43Z saulius 

The following automatic conversions were performed:

'_symmetry_cell_setting' value 'Monoclinic' changed to 'monoclinic'
according to /home/saulius/struct/CIF-dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.1 from 2010-06-29.

Automatic conversion script
Id: cif_fix_values 1715 2011-07-08 13:25:40Z adriana 
;
_cod_original_cell_volume        654.459(10)
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               2211008
_cod_database_fobs_code          2211008
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -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
Br Br1 0.357551(11) 0.79782(5) 0.574543(6) 0.02143(3) Uani d . 1
O O1 0.28008(10) 0.9906(3) 0.10248(7) 0.0264(2) Uani d . 1
O O2 0.91154(9) 1.0452(3) 0.14142(6) 0.02069(17) Uani d . 1
C C1 0.63215(12) 0.8777(3) 0.22358(8) 0.0174(2) Uani d . 1
H H1A 0.6200 0.7819 0.2707 0.021 Uiso calc R 1
C C2 0.76174(12) 0.9006(3) 0.21518(8) 0.0187(2) Uani d . 1
H H2A 0.8362 0.8197 0.2566 0.022 Uiso calc R 1
C C3 0.78077(11) 1.0448(3) 0.14462(8) 0.01631(18) Uani d . 1
C C4 0.67021(12) 1.1740(3) 0.08284(8) 0.01701(18) Uani d . 1
H H4A 0.6829 1.2756 0.0364 0.020 Uiso calc R 1
C C5 0.54069(11) 1.1481(3) 0.09195(7) 0.01675(19) Uani d . 1
H H5A 0.4666 1.2326 0.0508 0.020 Uiso calc R 1
C C6 0.51905(11) 0.9985(3) 0.16124(7) 0.01585(18) Uani d . 1
C C7 0.37727(12) 0.9554(3) 0.16440(8) 0.0184(2) Uani d . 1
C C8 0.35654(12) 0.8662(3) 0.24421(8) 0.0190(2) Uani d . 1
H H8A 0.4259 0.9089 0.2923 0.023 Uiso calc R 1
C C9 0.24013(12) 0.7255(3) 0.24851(8) 0.0180(2) Uani d . 1
H H9A 0.1745 0.6783 0.1990 0.022 Uiso calc R 1
C C10 0.20588(11) 0.6387(3) 0.32349(8) 0.01608(18) Uani d . 1
C C11 0.08441(11) 0.4626(3) 0.31654(8) 0.01783(19) Uani d . 1
H H11A 0.0293 0.3963 0.2651 0.021 Uiso calc R 1
C C12 0.04532(12) 0.3856(3) 0.38569(9) 0.0199(2) Uani d . 1
H H12A -0.0359 0.2697 0.3801 0.024 Uiso calc R 1
C C13 0.12654(12) 0.4804(3) 0.46296(8) 0.0186(2) Uani d . 1
H H13A 0.1009 0.4290 0.5094 0.022 Uiso calc R 1
C C14 0.24757(11) 0.6546(3) 0.46931(7) 0.01674(19) Uani d . 1
C C15 0.28875(11) 0.7349(3) 0.40159(7) 0.0165(2) Uani d . 1
H H15A 0.3701 0.8508 0.4076 0.020 Uiso calc R 1
C C16 0.93644(13) 1.1917(4) 0.07045(9) 0.0230(2) Uani d . 1
H H16A 1.0320 1.1802 0.0760 0.034 Uiso calc R 1
H H16B 0.9075 1.4270 0.0651 0.034 Uiso calc R 1
H H16C 0.8865 1.0662 0.0226 0.034 Uiso calc R 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'
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
C3 O2 C16 117.54(10)
C2 C1 C6 120.37(11)
C2 C1 H1A 119.8
C6 C1 H1A 119.8
C1 C2 C3 120.13(11)
C1 C2 H2A 119.9
C3 C2 H2A 119.9
O2 C3 C4 124.17(11)
O2 C3 C2 115.41(10)
C4 C3 C2 120.42(11)
C5 C4 C3 118.80(11)
C5 C4 H4A 120.6
C3 C4 H4A 120.6
C4 C5 C6 121.70(11)
C4 C5 H5A 119.2
C6 C5 H5A 119.2
C5 C6 C1 118.55(10)
C5 C6 C7 118.98(10)
C1 C6 C7 122.38(11)
O1 C7 C8 121.02(11)
O1 C7 C6 120.84(11)
C8 C7 C6 118.14(11)
C9 C8 C7 121.48(11)
C9 C8 H8A 119.3
C7 C8 H8A 119.3
C8 C9 C10 126.44(11)
C8 C9 H9A 116.8
C10 C9 H9A 116.8
C11 C10 C15 119.07(11)
C11 C10 C9 118.68(11)
C15 C10 C9 122.23(10)
C12 C11 C10 120.72(12)
C12 C11 H11A 119.6
C10 C11 H11A 119.6
C13 C12 C11 120.50(11)
C13 C12 H12A 119.8
C11 C12 H12A 119.8
C12 C13 C14 118.38(11)
C12 C13 H13A 120.8
C14 C13 H13A 120.8
C15 C14 C13 122.33(11)
C15 C14 Br1 118.76(9)
C13 C14 Br1 118.89(9)
C14 C15 C10 119.01(10)
C14 C15 H15A 120.5
C10 C15 H15A 120.5
O2 C16 H16A 109.5
O2 C16 H16B 109.5
H16A C16 H16B 109.5
O2 C16 H16C 109.5
H16A C16 H16C 109.5
H16B C16 H16C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Br1 C14 1.9017(12)
O1 C7 1.2286(16)
O2 C3 1.3632(14)
O2 C16 1.4312(18)
C1 C2 1.3861(16)
C1 C6 1.4048(16)
C1 H1A 0.9300
C2 C3 1.3961(18)
C2 H2A 0.9300
C3 C4 1.3957(17)
C4 C5 1.3910(16)
C4 H4A 0.9300
C5 C6 1.3960(17)
C5 H5A 0.9300
C6 C7 1.4857(16)
C7 C8 1.4833(18)
C8 C9 1.3391(16)
C8 H8A 0.9300
C9 C10 1.4664(17)
C9 H9A 0.9300
C10 C11 1.4000(16)
C10 C15 1.4042(17)
C11 C12 1.3898(19)
C11 H11A 0.9300
C12 C13 1.3865(19)
C12 H12A 0.9300
C13 C14 1.3941(17)
C13 H13A 0.9300
C14 C15 1.3818(17)
C15 H15A 0.9300
C16 H16A 0.9600
C16 H16B 0.9600
C16 H16C 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
_geom_hbond_publ_flag
C11 H11A O2 1_445 0.93 2.51 3.4060(16) 163 y
C16 H16A O1 1_655 0.96 2.57 3.5028(18) 165 y
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 0.15(19)
C16 O2 C3 C4 0.81(18)
C16 O2 C3 C2 -179.74(12)
C1 C2 C3 O2 -178.05(11)
C1 C2 C3 C4 1.43(19)
O2 C3 C4 C5 177.76(12)
C2 C3 C4 C5 -1.67(18)
C3 C4 C5 C6 0.35(19)
C4 C5 C6 C1 1.18(19)
C4 C5 C6 C7 -175.49(12)
C2 C1 C6 C5 -1.43(18)
C2 C1 C6 C7 175.13(12)
C5 C6 C7 O1 13.2(2)
C1 C6 C7 O1 -163.35(14)
C5 C6 C7 C8 -167.25(12)
C1 C6 C7 C8 16.21(18)
O1 C7 C8 C9 19.6(2)
C6 C7 C8 C9 -159.93(12)
C7 C8 C9 C10 -177.52(12)
C8 C9 C10 C11 -173.94(13)
C8 C9 C10 C15 7.93(19)
C15 C10 C11 C12 0.51(18)
C9 C10 C11 C12 -177.68(11)
C10 C11 C12 C13 -0.39(19)
C11 C12 C13 C14 0.14(19)
C12 C13 C14 C15 -0.02(18)
C12 C13 C14 Br1 178.23(9)
C13 C14 C15 C10 0.15(17)
Br1 C14 C15 C10 -178.11(9)
C11 C10 C15 C14 -0.38(17)
C9 C10 C15 C14 177.74(11)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30655088
