#------------------------------------------------------------------------------
#$Date: 2016-02-14 16:26:36 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176435 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/39/2003981.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_2003981
loop_
_publ_author_name
'Banwell, M. G.'
'Bridges, V. S.'
'Hockless, D. C. R.'
_publ_section_title
;
 1-[2(Z)-Bromo-3-phenyl-2-propenyl]pyridin-2(1H)-one
;
_journal_issue                   10
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              2128
_journal_page_last               2129
_journal_paper_doi               10.1107/S0108270195005579
_journal_volume                  51
_journal_year                    1995
_chemical_formula_moiety         'C14 H12 Br1 N1 O1'
_chemical_formula_sum            'C14 H12 Br N O'
_chemical_formula_weight         290.16
_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'
_cell_angle_alpha                90
_cell_angle_beta                 104.03(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   9.374(2)
_cell_length_b                   11.2170(10)
_cell_length_c                   12.015(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    213
_cell_measurement_theta_max      50
_cell_measurement_theta_min      49
_cell_volume                     1225.7(4)
_computing_cell_refinement       'MSC/AFC Diffractometer Control Software'
_computing_data_collection
;
MSC/AFC Diffractometer Control Software
(Molecular Structure Corporation, 1988)
;
_computing_data_reduction
'TEXSAN (Molecular Structure Corporation, 1993)'
_computing_publication_material  TEXSAN
_computing_structure_refinement  TEXSAN
_computing_structure_solution    'PATTY in DIRDIF (Beurskens et al., 1992)'
_diffrn_ambient_temperature      213
_diffrn_measurement_device       'Rigaku AFC-6R'
_diffrn_measurement_method       ω/2θ
_diffrn_radiation_monochromator  'equatorial graphite'
_diffrn_radiation_source         'Rigaku RU200B rotating Cu anode'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.5418
_diffrn_reflns_av_R_equivalents  5.78
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -010
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2043
_diffrn_reflns_theta_max         60.06
_diffrn_standards_decay_%        -02.18
_diffrn_standards_interval_count 150
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    4.423
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  .899
_exptl_absorpt_correction_type
'empirical based on azimuthal (\y) scans (North, Phillips & Mathews, 1968)'
_exptl_absorpt_process_details
;
empirical based on azimuthal (ψ) scans (North, Phillips & Mathews, 1968)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.572
_exptl_crystal_description       'irregular prism'
_exptl_crystal_F_000             584.00
_exptl_crystal_size_max          .280
_exptl_crystal_size_mid          .160
_exptl_crystal_size_min          .120
_refine_diff_density_max         .53
_refine_diff_density_min         -0.56
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_obs   2.410
_refine_ls_hydrogen_treatment    noref
_refine_ls_matrix_type           full
_refine_ls_number_parameters     154
_refine_ls_number_reflns         1632
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0397
_refine_ls_R_factor_obs          .0350
_refine_ls_shift/esd_max         .0010
_refine_ls_structure_factor_coef F
_refine_ls_weighting_scheme      unit
_refine_ls_wR_factor_all         .0397
_refine_ls_wR_factor_obs         .0380
_reflns_number_observed          1632
_reflns_number_total             1943
_reflns_observed_criterion       I>3\s(I)
_cod_data_source_file            as1181.cif
_cod_data_source_block           structure
_cod_original_cell_volume        1225.7(3)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_original_formula_sum        'C14 H12 Br1 N1 O1'
_cod_database_code               2003981
loop_
_symmetry_equiv_pos_as_xyz
'   +x,   +y,   +z'
'   -x,1/2+y,1/2-z'
'   -x,   -y,   -z'
'   +x,1/2-y,1/2+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_thermal_displace_type
Br(1) .13557(5) .07867(4) .28446(4) .04470(10) Uani
O(1) .4124(3) .2746(3) .0691(2) .0429(9) Uani
N(1) .3574(3) .2900(3) .2433(3) .0269(9) Uani
C(2) .3599(4) .3356(4) .1356(3) .0290(10) Uani
C(3) .2998(5) .4527(4) .1125(3) .0350(10) Uani
C(4) .2433(5) .5129(4) .1886(4) .0360(10) Uani
C(5) .2436(4) .4626(4) .2961(4) .0340(10) Uani
C(6) .3012(4) .3529(4) .3207(3) .0310(10) Uani
C(1') .4153(4) .1689(4) .2724(4) .0350(10) Uani
C(2') .3049(4) .0735(4) .2215(3) .0330(10) Uani
C(3') .3227(4) -.0056(4) .1453(4) .0340(10) Uani
C(1'') .2354(4) -0.1045(3) .0824(3) .0300(10) Uani
C(2'') .3038(4) -0.1748(3) .0142(4) .0330(10) Uani
C(3'') .2279(5) -0.2650(4) -.0536(4) .0380(10) Uani
C(4'') .0833(5) -0.2880(4) -.0545(4) .0400(10) Uani
C(5'') .0151(5) -0.2206(4) .0130(4) .0430(10) Uani
C(6'') .0894(5) -0.1303(4) .0810(4) .0400(10) Uani
H(3) .2997 .4891 .0410 .0417 Uiso
H(4) .2029 .5900 .1696 .0427 Uiso
H(5) .2041 .5052 .3501 .0400 Uiso
H(6) .3030 .3184 .3933 .0372 Uiso
H(1'a) .4407 .1605 .3535 .0416 Uiso
H(1'b) .5007 .1585 .2440 .0416 Uiso
H(3') .4146 .0032 .1258 .0400 Uiso
H(2'') .4038 -0.1603 .0143 .0391 Uiso
H(3'') .2759 -0.3115 -0.0998 .0457 Uiso
H(4'') .0311 -0.3498 -0.1013 .0481 Uiso
H(5'') -0.0846 -0.2363 .0128 .0513 Uiso
H(6'') .0406 -0.0851 .1275 .0478 Uiso
loop_
_atom_type_symbol
_atom_type_scat_source
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
C
;
International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and
6.1.1.4)
;
.018 .009
H
;
International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and
6.1.1.4)
;
.000 .000
Br
;
International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and
6.1.1.4)
;
-0.676 1.280
N
;
International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and
6.1.1.4)
;
.031 .018
O
;
International Tables for Crystallography (1992, Vol. C, Tables 4.2.6.8 and
6.1.1.4)
;
.049 .032
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_publ_flag
C(1') N(1) C(2) 118.0(3) yes
C(1') N(1) C(6) 119.6(3) yes
C(2) N(1) C(6) 122.4(3) no
N(1) C(1') C(2') 112.3(3) yes
C(2'') C(1'') C(3') 116.6(4) yes
C(2'') C(1'') C(6'') 117.6(4) no
C(3') C(1'') C(6'') 125.7(4) yes
Br(1) C(2') C(1') 111.7(3) yes
Br(1) C(2') C(3') 123.5(3) yes
C(1') C(2') C(3') 124.7(4) yes
O(1) C(2) N(1) 119.6(4) no
O(1) C(2) C(3) 125.5(4) no
N(1) C(2) C(3) 115.0(3) no
C(1'') C(2'') C(3'') 120.9(4) no
C(2) C(3) C(4) 122.1(4) no
C(1'') C(3') C(2') 135.8(4) yes
C(2'') C(3'') C(4'') 120.4(4) no
C(3) C(4) C(5) 120.6(4) no
C(3'') C(4'') C(5'') 119.3(4) no
C(4) C(5) C(6) 118.6(4) no
C(4'') C(5'') C(6'') 120.9(4) no
N(1) C(6) C(5) 121.4(4) no
C(1'') C(6'') C(5'') 120.9(4) no
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
Br(1) C(2') 1.918(4) yes
O(1) C(2) 1.241(5) yes
N(1) C(1') 1.473(5) yes
N(1) C(2) 1.396(5) no
N(1) C(6) 1.370(5) no
C(1') C(2') 1.511(6) yes
C(1'') C(2'') 1.400(6) no
C(1'') C(3') 1.473(6) yes
C(1'') C(6'') 1.395(6) no
C(2') C(3') 1.315(6) yes
C(2) C(3) 1.430(6) no
C(2'') C(3'') 1.383(6) no
C(3) C(4) 1.344(6) no
C(3'') C(4'') 1.378(6) no
C(4) C(5) 1.409(6) no
C(4'') C(5'') 1.374(6) no
C(5) C(6) 1.348(6) no
C(5'') C(6'') 1.379(6) no
