#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/88/2218890.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_2218890
loop_
_publ_author_name
'Fun, Hoong-Kun'
'Jebas, Samuel Robinson'
'Patil, P. S.'
'Dharmaprakash, S. M.'
_publ_section_title
;
 (E)-3-(2-Chlorophenyl)-1-(3-methoxyphenyl)prop-2-en-1-one
;
_journal_coeditor_code           BI2296
_journal_issue                   8
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o1525
_journal_paper_doi               10.1107/S1600536808021910
_journal_volume                  64
_journal_year                    2008
_chemical_formula_iupac          'C16 H13 Cl O2'
_chemical_formula_moiety         'C16 H13 Cl O2'
_chemical_formula_sum            'C16 H13 Cl O2'
_chemical_formula_weight         272.71
_chemical_name_common
;
(E)-3-(2-Chlorophenyl)-1-(3-methoxyphenyl)prop-2-en-1-one
;
_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                87.3920(10)
_cell_angle_beta                 82.1470(10)
_cell_angle_gamma                74.7940(10)
_cell_formula_units_Z            2
_cell_length_a                   7.7352(2)
_cell_length_b                   8.1405(2)
_cell_length_c                   10.7411(2)
_cell_measurement_reflns_used    7792
_cell_measurement_temperature    100.00(10)
_cell_measurement_theta_max      37.52
_cell_measurement_theta_min      2.22
_cell_volume                     646.52(3)
_computing_cell_refinement       'SAINT (Bruker, 2005)'
_computing_data_collection       'APEX2 (Bruker, 2005)'
_computing_data_reduction        'SAINT (Bruker, 2005)'
_computing_molecular_graphics    'SHELXTL (Sheldrick, 2008)'
_computing_publication_material
;
SHELXTL (Sheldrick, 2008) and PLATON (Spek, 2003)
;
_computing_structure_refinement  'SHELXTL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXTL (Sheldrick, 2008)'
_diffrn_ambient_temperature      100.0(10)
_diffrn_measured_fraction_theta_full 0.987
_diffrn_measured_fraction_theta_max 0.987
_diffrn_measurement_device_type  'Bruker SMART APEXII CCD'
_diffrn_measurement_method       'φ and 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  0.0247
_diffrn_reflns_av_sigmaI/netI    0.0259
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            17497
_diffrn_reflns_theta_full        31.68
_diffrn_reflns_theta_max         31.68
_diffrn_reflns_theta_min         2.59
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.289
_exptl_absorpt_correction_T_max  0.9552
_exptl_absorpt_correction_T_min  0.8988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Bruker, 2005)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.401
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             284
_exptl_crystal_size_max          0.38
_exptl_crystal_size_mid          0.30
_exptl_crystal_size_min          0.16
_refine_diff_density_max         0.526
_refine_diff_density_min         -0.231
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     173
_refine_ls_number_reflns         4314
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.060
_refine_ls_R_factor_all          0.0468
_refine_ls_R_factor_gt           0.0374
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0513P)²+0.1689P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0958
_refine_ls_wR_factor_ref         0.1009
_reflns_number_gt                3644
_reflns_number_total             4314
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            bi2296.cif
_cod_data_source_block           I
_cod_database_code               2218890
_cod_database_fobs_code          2218890
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
Cl Cl1 1.15204(4) 0.08594(3) -0.41471(2) 0.02216(8) Uani d . 1
O O1 0.78728(11) 0.44819(10) -0.05788(8) 0.02200(17) Uani d . 1
O O2 0.46589(11) 0.70028(11) 0.36344(8) 0.02281(17) Uani d . 1
C C1 1.29054(14) -0.01282(13) -0.30363(10) 0.01529(19) Uani d . 1
C C2 1.44112(15) -0.14294(13) -0.34590(10) 0.0184(2) Uani d . 1
H H2A 1.4678 -0.1705 -0.4307 0.022 Uiso calc R 1
C C3 1.55059(15) -0.23075(13) -0.25988(11) 0.0196(2) Uani d . 1
H H3A 1.6517 -0.3178 -0.2870 0.024 Uiso calc R 1
C C4 1.51011(15) -0.18945(13) -0.13323(11) 0.0189(2) Uani d . 1
H H4A 1.5830 -0.2495 -0.0755 0.023 Uiso calc R 1
C C5 1.36046(14) -0.05817(13) -0.09349(10) 0.0172(2) Uani d . 1
H H5A 1.3348 -0.0311 -0.0086 0.021 Uiso calc R 1
C C6 1.24650(14) 0.03518(12) -0.17720(10) 0.01485(19) Uani d . 1
C C7 1.09255(14) 0.17825(13) -0.13473(10) 0.01589(19) Uani d . 1
H H7A 1.0407 0.2526 -0.1957 0.019 Uiso calc R 1
C C8 1.02124(15) 0.20974(13) -0.01471(10) 0.0173(2) Uani d . 1
H H8A 1.0667 0.1341 0.0477 0.021 Uiso calc R 1
C C9 0.87148(14) 0.36241(13) 0.02113(10) 0.01643(19) Uani d . 1
C C10 0.82784(14) 0.40997(13) 0.15679(10) 0.01584(19) Uani d . 1
C C11 0.94385(16) 0.34122(14) 0.24498(11) 0.0207(2) Uani d . 1
H H11A 1.0518 0.2604 0.2210 0.025 Uiso calc R 1
C C12 0.89719(18) 0.39431(15) 0.36938(11) 0.0248(2) Uani d . 1
H H12A 0.9748 0.3489 0.4284 0.030 Uiso calc R 1
C C13 0.73691(17) 0.51359(14) 0.40576(11) 0.0218(2) Uani d . 1
H H13A 0.7062 0.5474 0.4892 0.026 Uiso calc R 1
C C14 0.62110(15) 0.58335(13) 0.31749(10) 0.0173(2) Uani d . 1
C C15 0.66548(14) 0.53249(13) 0.19298(10) 0.01602(19) Uani d . 1
H H15A 0.5882 0.5793 0.1341 0.019 Uiso calc R 1
C C16 0.34703(16) 0.78256(16) 0.27587(12) 0.0253(2) Uani d . 1
H H16A 0.2445 0.8619 0.3194 0.038 Uiso calc R 1
H H16B 0.3070 0.6989 0.2355 0.038 Uiso calc R 1
H H16C 0.4096 0.8423 0.2137 0.038 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'
Cl Cl 0.1484 0.1585 '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
C14 O2 C16 117.57(9)
C2 C1 C6 122.55(10)
C2 C1 Cl1 116.93(8)
C6 C1 Cl1 120.49(8)
C3 C2 C1 119.02(10)
C3 C2 H2A 120.5
C1 C2 H2A 120.5
C2 C3 C4 120.35(10)
C2 C3 H3A 119.8
C4 C3 H3A 119.8
C5 C4 C3 119.61(10)
C5 C4 H4A 120.2
C3 C4 H4A 120.2
C4 C5 C6 122.09(10)
C4 C5 H5A 119.0
C6 C5 H5A 119.0
C1 C6 C5 116.37(9)
C1 C6 C7 122.05(9)
C5 C6 C7 121.56(9)
C8 C7 C6 124.89(10)
C8 C7 H7A 117.6
C6 C7 H7A 117.6
C7 C8 C9 121.58(10)
C7 C8 H8A 119.2
C9 C8 H8A 119.2
O1 C9 C8 121.09(10)
O1 C9 C10 120.76(10)
C8 C9 C10 118.14(9)
C11 C10 C15 120.12(10)
C11 C10 C9 122.44(10)
C15 C10 C9 117.41(9)
C10 C11 C12 119.56(10)
C10 C11 H11A 120.2
C12 C11 H11A 120.2
C13 C12 C11 120.58(11)
C13 C12 H12A 119.7
C11 C12 H12A 119.7
C12 C13 C14 119.96(10)
C12 C13 H13A 120.0
C14 C13 H13A 120.0
O2 C14 C15 124.45(10)
O2 C14 C13 115.23(10)
C15 C14 C13 120.32(10)
C14 C15 C10 119.46(10)
C14 C15 H15A 120.3
C10 C15 H15A 120.3
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
Cl1 C1 1.7400(11)
O1 C9 1.2208(14)
O2 C14 1.3684(13)
O2 C16 1.4264(15)
C1 C2 1.3917(14)
C1 C6 1.4018(14)
C2 C3 1.3849(16)
C2 H2A 0.930
C3 C4 1.3899(16)
C3 H3A 0.930
C4 C5 1.3863(15)
C4 H4A 0.930
C5 C6 1.4021(15)
C5 H5A 0.930
C6 C7 1.4680(14)
C7 C8 1.3391(15)
C7 H7A 0.930
C8 C9 1.4836(15)
C8 H8A 0.930
C9 C10 1.4952(14)
C10 C11 1.3915(15)
C10 C15 1.4028(14)
C11 C12 1.3933(16)
C11 H11A 0.930
C12 C13 1.3796(17)
C12 H12A 0.930
C13 C14 1.3929(16)
C13 H13A 0.930
C14 C15 1.3886(14)
C15 H15A 0.930
C16 H16A 0.960
C16 H16B 0.960
C16 H16C 0.960
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
C2 H2A O2 1_644 0.93 2.50 3.3887(13) 161.1
C4 H4A O1 1_645 0.93 2.57 3.3003(13) 136.1
C16 H16B O1 2_665 0.96 2.58 3.4899(14) 158.4
C16 H16C Cg1 2_765 0.96 2.82 3.6137(14) 135
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 1.08(15)
Cl1 C1 C2 C3 -176.96(8)
C1 C2 C3 C4 0.12(16)
C2 C3 C4 C5 -0.79(16)
C3 C4 C5 C6 0.30(16)
C2 C1 C6 C5 -1.52(15)
Cl1 C1 C6 C5 176.45(7)
C2 C1 C6 C7 176.86(9)
Cl1 C1 C6 C7 -5.17(13)
C4 C5 C6 C1 0.82(15)
C4 C5 C6 C7 -177.57(10)
C1 C6 C7 C8 165.91(10)
C5 C6 C7 C8 -15.79(15)
C6 C7 C8 C9 176.74(9)
C7 C8 C9 O1 12.94(16)
C7 C8 C9 C10 -166.25(9)
O1 C9 C10 C11 -164.94(10)
C8 C9 C10 C11 14.25(15)
O1 C9 C10 C15 13.15(15)
C8 C9 C10 C15 -167.66(9)
C15 C10 C11 C12 0.30(16)
C9 C10 C11 C12 178.33(10)
C10 C11 C12 C13 0.30(18)
C11 C12 C13 C14 -0.69(18)
C16 O2 C14 C15 -3.86(15)
C16 O2 C14 C13 176.68(10)
C12 C13 C14 O2 179.96(10)
C12 C13 C14 C15 0.48(17)
O2 C14 C15 C10 -179.32(9)
C13 C14 C15 C10 0.11(15)
C11 C10 C15 C14 -0.50(15)
C9 C10 C15 C14 -178.64(9)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30655551
