#------------------------------------------------------------------------------
#$Date: 2017-10-13 03:48:21 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201957 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/01/24/2012420.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_2012420
loop_
_publ_author_name
'Jeyabharathi, A.'
'Ponnuswamy, M. N.'
'Nanjundan, S.'
'Fun, Hoong-Kun'
'Suchada Chantrapromma'
'Usman, Anwar'
'Razak, Ibrahim Abdul'
_publ_section_title
;
 4-[3-(3,4-Dimethoxyphenyl)prop-2-enoyl]phenyl methacrylate and
 4-[3-(2-bromophenyl)prop-2-enoyl]phenyl methacrylate
;
_journal_issue                   1
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              o26
_journal_page_last               o28
_journal_paper_doi               10.1107/S0108270101018273
_journal_volume                  58
_journal_year                    2002
_chemical_formula_iupac          'C21 H20 O5'
_chemical_formula_moiety         'C21 H20 O5'
_chemical_formula_sum            'C21 H20 O5'
_chemical_formula_weight         352.37
_chemical_name_systematic
;
4-[3-(3,4-Dimethoxyphenyl)prop-2-enoyl]phenyl methacrylate
;
_space_group_IT_number           15
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-C 2yc'
_symmetry_space_group_name_H-M   'C 1 2/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                 109.680(10)
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   13.381(2)
_cell_length_b                   20.813(2)
_cell_length_c                   13.881(2)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      25.0
_cell_measurement_theta_min      4.1
_cell_volume                     3640.0(9)
_computing_cell_refinement       'CAD-4 Software'
_computing_data_collection       'CAD-4 Software (Enraf-Nonius, 1989)'
_computing_data_reduction        'SDP (Frenz, 1978)'
_computing_molecular_graphics    'ZORTEP (Zsolnai,1997)'
_computing_publication_material
;
PARST (Nardelli, 1995) and PLATON (Spek, 1990)
;
_computing_structure_refinement  'SHELXTL (Sheldrick, 1997)'
_computing_structure_solution    'SHELXTL (Sheldrick, 1997)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full .991
_diffrn_measured_fraction_theta_max .991
_diffrn_measurement_device_type  'Enraf-Nonius CAD-4'
_diffrn_measurement_method       ω/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54180
_diffrn_reflns_av_R_equivalents  .0498
_diffrn_reflns_av_sigmaI/netI    .0306
_diffrn_reflns_limit_h_max       16
_diffrn_reflns_limit_h_min       -2
_diffrn_reflns_limit_k_max       25
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            3812
_diffrn_reflns_theta_full        72.02
_diffrn_reflns_theta_max         72.02
_diffrn_reflns_theta_min         4.10
_diffrn_standards_decay_%        <0.1
_diffrn_standards_interval_count 200
_diffrn_standards_interval_time  120
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    .752
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.286
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             1488
_exptl_crystal_size_max          .3
_exptl_crystal_size_mid          .2
_exptl_crystal_size_min          .2
_refine_diff_density_max         .271
_refine_diff_density_min         -.219
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.040
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     238
_refine_ls_number_reflns         3549
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.040
_refine_ls_R_factor_all          .0790
_refine_ls_R_factor_gt           .0536
_refine_ls_shift/su_max          <0.001
_refine_ls_shift/su_mean         .000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w = 1/[σ²(Fo²)+(0.0922P)²+0.6924P] where P = (Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          .1448
_refine_ls_wR_factor_ref         .1628
_reflns_number_gt                2444
_reflns_number_total             3549
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            da1204.cif
_cod_data_source_block           I
_cod_original_cell_volume        3640.0(8)
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2012420
_cod_database_fobs_code          2012420
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y, -z+1/2'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y, z-1/2'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z-1/2'
loop_
_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
_atom_site_type_symbol
C1 .48118(16) .16042(10) .11251(15) .0637(5) Uani d . 1 . . C
C10 -.07604(15) .06351(10) .11849(14) .0613(5) Uani d . 1 . . C
O5 .49370(12) .04848(7) .11396(13) .0766(4) Uani d . 1 . . O
C3 .32772(16) .09852(9) .10879(15) .0608(5) Uani d . 1 . . C
H3 .2951 .0590 .1082 .073 Uiso calc R 1 . . H
C2 .43169(16) .10073(9) .11195(15) .0613(5) Uani d . 1 . . C
O4 .58327(12) .15740(7) .11380(14) .0803(5) Uani d . 1 . . O
C4 .27059(16) .15542(9) .10639(15) .0636(5) Uani d . 1 . . C
C9 -.01194(16) .11840(10) .10340(16) .0682(5) Uani d . 1 . . C
O2 -.26290(13) -.08349(9) .17100(11) .0855(5) Uani d . 1 . . O
C13 -.19997(17) -.03308(12) .15513(15) .0694(5) Uani d . 1 . . C
C17 -.32525(15) -.14995(9) .27588(17) .0662(5) Uani d . 1 . . C
C8 .09742(16) .10715(10) .10483(15) .0651(5) Uani d . 1 . . C
H8 .1227 .0653 .1078 .078 Uiso calc R 1 . . H
C16 -.25796(16) -.09516(10) .26773(16) .0665(5) Uani d . 1 . . C
C15 -.16951(17) .07756(12) .13748(17) .0737(6) Uani d . 1 . . C
H15 -.1904 .1202 .1377 .088 Uiso calc R 1 . . H
O1 -.04908(14) .17312(8) .09273(17) .1000(6) Uani d . 1 . . O
C7 .16029(17) .15598(10) .10187(16) .0672(5) Uani d . 1 . . C
H7 .1293 .1964 .0961 .081 Uiso calc R 1 . . H
C11 -.04766(16) -.00037(10) .11653(15) .0656(5) Uani d . 1 . . C
H11 .0141 -.0107 .1033 .079 Uiso calc R 1 . . H
O3 -.20585(16) -.06307(9) .33833(13) .0983(6) Uani d . 1 . . O
C20 .44644(19) -.01285(10) .1069(2) .0784(6) Uani d . 1 . . C
H20A .4981 -.0453 .1092 .118 Uiso calc R 1 . . H
H20B .3883 -.0161 .0436 .118 Uiso calc R 1 . . H
H20C .4208 -.0188 .1631 .118 Uiso calc R 1 . . H
C5 .32143(18) .21358(10) .10825(18) .0714(5) Uani d . 1 . . C
H5 .2848 .2516 .1077 .086 Uiso calc R 1 . . H
C19 -.3193(2) -.16732(11) .3809(2) .0808(6) Uani d . 1 . . C
H19A -.3531 -.2081 .3799 .121 Uiso calc R 1 . . H
H19B -.3546 -.1351 .4071 .121 Uiso calc R 1 . . H
H19C -.2462 -.1700 .4239 .121 Uiso calc R 1 . . H
C6 .42588(18) .21615(10) .11093(17) .0719(6) Uani d . 1 . . C
H6 .4585 .2557 .1117 .086 Uiso calc R 1 . . H
C14 -.23157(17) .02958(13) .15588(17) .0776(6) Uani d . 1 . . C
H14 -.2938 .0395 .1686 .093 Uiso calc R 1 . . H
C18 -.38625(19) -.18055(12) .1917(2) .0881(7) Uani d . 1 . . C
H18A -.4282 -.2150 .1974 .106 Uiso calc R 1 . . H
H18B -.3866 -.1674 .1276 .106 Uiso calc R 1 . . H
C21 .6354(2) .21722(12) .1145(2) .0877(7) Uani d . 1 . . C
H21A .7059 .2095 .1138 .132 Uiso calc R 1 . . H
H21B .6392 .2408 .1751 .132 Uiso calc R 1 . . H
H21C .5963 .2417 .0552 .132 Uiso calc R 1 . . H
C12 -.10995(18) -.04891(11) .13405(16) .0705(5) Uani d . 1 . . C
H12 -.0911 -.0917 .1316 .085 Uiso calc R 1 . . H
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C .0181 .0091 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H .0000 .0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O .0492 .0322 '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
_geom_angle_publ_flag
O4 C1 C6 124.93(18) yes
O4 C1 C2 115.32(18) yes
C6 C1 C2 119.75(19) ?
C11 C10 C15 118.3(2) ?
C11 C10 C9 124.07(18) yes
C15 C10 C9 117.59(19) yes
C2 O5 C20 117.66(16) ?
C2 C3 C4 120.57(17) ?
C2 C3 H3 119.7 ?
C4 C3 H3 119.7 ?
O5 C2 C3 125.13(17) yes
O5 C2 C1 114.99(17) yes
C3 C2 C1 119.87(18) ?
C1 O4 C21 116.50(17) ?
C5 C4 C3 118.48(19) ?
C5 C4 C7 118.57(19) ?
C3 C4 C7 122.95(18) ?
O1 C9 C8 120.4(2) ?
O1 C9 C10 119.96(19) ?
C8 C9 C10 119.56(18) ?
C16 O2 C13 117.39(16) ?
C14 C13 C12 121.7(2) ?
C14 C13 O2 120.3(2) ?
C12 C13 O2 117.9(2) ?
C18 C17 C19 124.0(2) ?
C18 C17 C16 120.5(2) ?
C19 C17 C16 115.56(19) ?
C7 C8 C9 120.91(19) ?
C7 C8 H8 119.5 ?
C9 C8 H8 119.5 ?
O3 C16 O2 122.4(2) ?
O3 C16 C17 124.7(2) ?
O2 C16 C17 112.88(18) ?
C14 C15 C10 121.3(2) ?
C14 C15 H15 119.4 ?
C10 C15 H15 119.4 ?
C8 C7 C4 129.5(2) yes
C8 C7 H7 115.3 ?
C4 C7 H7 115.3 ?
C12 C11 C10 120.82(19) ?
C12 C11 H11 119.6 ?
C10 C11 H11 119.6 ?
O5 C20 H20A 109.5 ?
O5 C20 H20B 109.5 ?
H20A C20 H20B 109.5 ?
O5 C20 H20C 109.5 ?
H20A C20 H20C 109.5 ?
H20B C20 H20C 109.5 ?
C4 C5 C6 121.25(19) ?
C4 C5 H5 119.4 ?
C6 C5 H5 119.4 ?
C17 C19 H19A 109.5 ?
C17 C19 H19B 109.5 ?
H19A C19 H19B 109.5 ?
C17 C19 H19C 109.5 ?
H19A C19 H19C 109.5 ?
H19B C19 H19C 109.5 ?
C1 C6 C5 120.07(19) ?
C1 C6 H6 120.0 ?
C5 C6 H6 120.0 ?
C13 C14 C15 118.8(2) ?
C13 C14 H14 120.6 ?
C15 C14 H14 120.6 ?
C17 C18 H18A 120.0 ?
C17 C18 H18B 120.0 ?
H18A C18 H18B 120.0 ?
O4 C21 H21A 109.5 ?
O4 C21 H21B 109.5 ?
H21A C21 H21B 109.5 ?
O4 C21 H21C 109.5 ?
H21A C21 H21C 109.5 ?
H21B C21 H21C 109.5 ?
C13 C12 C11 119.1(2) ?
C13 C12 H12 120.4 ?
C11 C12 H12 120.4 ?
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
C1 O4 . 1.362(3) yes
C1 C6 . 1.372(3) ?
C1 C2 . 1.407(3) ?
C10 C11 . 1.386(3) ?
C10 C15 . 1.393(3) ?
C10 C9 . 1.485(3) ?
O5 C2 . 1.363(2) yes
O5 C20 . 1.413(2) yes
C3 C2 . 1.378(3) ?
C3 C4 . 1.404(3) ?
C3 H3 . .9300 ?
O4 C21 . 1.426(3) yes
C4 C5 . 1.385(3) ?
C4 C7 . 1.456(3) ?
C9 O1 . 1.231(2) yes
C9 C8 . 1.475(3) yes
O2 C16 . 1.344(3) yes
O2 C13 . 1.408(3) yes
C13 C14 . 1.372(3) ?
C13 C12 . 1.372(3) ?
C17 C18 . 1.340(3) ?
C17 C19 . 1.477(3) ?
C17 C16 . 1.481(3) ?
C8 C7 . 1.329(3) ?
C8 H8 . .9300 ?
C16 O3 . 1.197(2) yes
C15 C14 . 1.377(3) ?
C15 H15 . .9300 ?
C7 H7 . .9300 ?
C11 C12 . 1.382(3) ?
C11 H11 . .9300 ?
C20 H20A . .9600 ?
C20 H20B . .9600 ?
C20 H20C . .9600 ?
C5 C6 . 1.387(3) ?
C5 H5 . .9300 ?
C19 H19A . .9600 ?
C19 H19B . .9600 ?
C19 H19C . .9600 ?
C6 H6 . .9300 ?
C14 H14 . .9300 ?
C18 H18A . .9300 ?
C18 H18B . .9300 ?
C21 H21A . .9600 ?
C21 H21B . .9600 ?
C21 H21C . .9600 ?
C12 H12 . .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
_geom_hbond_publ_flag
C7 H7 O1 1_555 .93 2.42 2.784(3) 103 yes
C18 H18B O2 1_555 .93 2.34 2.685(3) 101 yes
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
_geom_torsion_publ_flag
C20 O5 C2 C3 3.5(3) ?
C20 O5 C2 C1 -176.04(19) ?
C4 C3 C2 O5 -179.67(18) ?
C4 C3 C2 C1 -.2(3) ?
O4 C1 C2 O5 .7(3) ?
C6 C1 C2 O5 -179.81(18) ?
O4 C1 C2 C3 -178.84(18) ?
C6 C1 C2 C3 .6(3) ?
C6 C1 O4 C21 .6(3) ?
C2 C1 O4 C21 -179.93(19) ?
C2 C3 C4 C5 -.6(3) ?
C2 C3 C4 C7 179.30(19) ?
C11 C10 C9 O1 170.4(2) ?
C15 C10 C9 O1 -10.8(3) ?
C11 C10 C9 C8 -11.7(3) ?
C15 C10 C9 C8 167.17(19) yes
C16 O2 C13 C14 -78.2(3) ?
C16 O2 C13 C12 105.0(2) ?
O1 C9 C8 C7 4.7(3) yes
C10 C9 C8 C7 -173.18(19) yes
C13 O2 C16 O3 2.8(3) ?
C13 O2 C16 C17 -178.71(18) ?
C18 C17 C16 O3 175.7(2) ?
C19 C17 C16 O3 -4.5(3) ?
C18 C17 C16 O2 -2.8(3) ?
C19 C17 C16 O2 177.09(18) ?
C11 C10 C15 C14 1.2(3) ?
C9 C10 C15 C14 -177.7(2) ?
C9 C8 C7 C4 177.5(2) yes
C5 C4 C7 C8 -176.0(2) yes
C3 C4 C7 C8 4.1(4) ?
C15 C10 C11 C12 -.7(3) ?
C9 C10 C11 C12 178.19(19) ?
C3 C4 C5 C6 .9(3) ?
C7 C4 C5 C6 -179.0(2) ?
O4 C1 C6 C5 179.1(2) ?
C2 C1 C6 C5 -.3(3) ?
C4 C5 C6 C1 -.5(3) ?
C12 C13 C14 C15 -1.7(3) ?
O2 C13 C14 C15 -178.35(18) ?
C10 C15 C14 C13 -.1(3) ?
C14 C13 C12 C11 2.2(3) ?
O2 C13 C12 C11 178.98(18) ?
C10 C11 C12 C13 -1.0(3) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30652335
