#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:42:48 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201978 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/22/56/2225661.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_2225661
loop_
_publ_author_name
'Maheta, Jeshal G.'
'Barot, Vijay M.'
'Jotani, Mukesh M.'
'Tiekink, Edward R. T.'
_publ_section_title
;
 (2E)-1-[2-Hydroxy-4-(2-methylpropoxy)phenyl]-3-(4-methylphenyl)prop-2-en-1-one
;
_journal_coeditor_code           PK2236
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o942
_journal_page_last               o943
_journal_paper_doi               10.1107/S1600536810010809
_journal_volume                  66
_journal_year                    2010
_chemical_formula_iupac          'C20 H22 O3'
_chemical_formula_moiety         'C20 H22 O3'
_chemical_formula_sum            'C20 H22 O3'
_chemical_formula_weight         310.38
_chemical_name_systematic
;
(2E)-1-[2-Hydroxy-4-(2-methylpropoxy)phenyl]-3-(4-
methylphenyl)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                74.740(2)
_cell_angle_beta                 78.857(2)
_cell_angle_gamma                74.103(2)
_cell_formula_units_Z            2
_cell_length_a                   6.7795(8)
_cell_length_b                   9.8830(12)
_cell_length_c                   13.9064(17)
_cell_measurement_reflns_used    3222
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      24.2
_cell_measurement_theta_min      2.8
_cell_volume                     857.12(18)
_computing_cell_refinement       'APEX2 and SAINT (Bruker, 2004)'
_computing_data_collection       'APEX2 (Bruker, 2004)'
_computing_data_reduction        'SAINT and XPREP (Bruker, 2004)'
_computing_molecular_graphics
'ORTEP-3 (Farrugia, 1997) and DIAMOND (Brandenburg, 2006)'
_computing_publication_material  'publCIF (Westrip, 2010)'
_computing_structure_refinement  'SHELXL97 (Sheldrick, 2008)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 2008)'
_diffrn_ambient_temperature      293(2)
_diffrn_measured_fraction_theta_full 0.992
_diffrn_measured_fraction_theta_max 0.992
_diffrn_measurement_device_type  'Bruker SMART APEX CCD diffractometer'
_diffrn_measurement_method       'ω and φ scans'
_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  0.019
_diffrn_reflns_av_sigmaI/netI    0.025
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       17
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            9290
_diffrn_reflns_theta_full        26.5
_diffrn_reflns_theta_max         26.5
_diffrn_reflns_theta_min         2.2
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.080
_exptl_absorpt_correction_T_max  0.991
_exptl_absorpt_correction_T_min  0.932
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.203
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             332
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.16
_refine_diff_density_min         -0.21
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.03
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     212
_refine_ls_number_reflns         3530
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.03
_refine_ls_R_factor_all          0.072
_refine_ls_R_factor_gt           0.049
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_max_lt       0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.067P)²+0.1242P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.126
_refine_ls_wR_factor_ref         0.142
_reflns_number_gt                2452
_reflns_number_total             3530
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            pk2236.cif
_cod_data_source_block           I
_cod_database_code               2225661
_cod_database_fobs_code          2225661
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
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.36395(17) 0.23227(14) 0.54491(10) 0.0693(4) Uani d . 1 . .
O O2 0.10785(17) 0.36469(16) 0.66378(11) 0.0787(4) Uani d . 1 . .
H H2o 0.1506 0.3135 0.6228 0.118 Uiso calc R 1 . .
O O3 0.34346(17) 0.64303(13) 0.82850(9) 0.0630(3) Uani d . 1 . .
C C1 1.4896(3) -0.0477(2) 0.18171(15) 0.0735(5) Uani d . 1 . .
H H1A 1.4928 -0.1427 0.1753 0.110 Uiso calc R 1 . .
H H1B 1.6102 -0.0506 0.2094 0.110 Uiso calc R 1 . .
H H1C 1.4874 0.0170 0.1167 0.110 Uiso calc R 1 . .
C C2 1.2985(2) 0.00433(18) 0.25032(12) 0.0541(4) Uani d . 1 . .
C C3 1.2904(2) 0.10836(18) 0.30244(13) 0.0571(4) Uani d . 1 . .
H H3 1.4053 0.1463 0.2947 0.069 Uiso calc R 1 . .
C C4 1.1166(2) 0.15668(17) 0.36524(12) 0.0531(4) Uani d . 1 . .
H H4 1.1164 0.2257 0.3997 0.064 Uiso calc R 1 . .
C C5 0.9411(2) 0.10332(16) 0.37782(11) 0.0460(4) Uani d . 1 . .
C C6 0.9496(2) -0.00067(17) 0.32580(12) 0.0529(4) Uani d . 1 . .
H H6 0.8345 -0.0381 0.3329 0.063 Uiso calc R 1 . .
C C7 1.1248(3) -0.04960(18) 0.26386(12) 0.0565(4) Uani d . 1 . .
H H7 1.1264 -0.1202 0.2306 0.068 Uiso calc R 1 . .
C C8 0.7507(2) 0.15052(17) 0.44205(11) 0.0500(4) Uani d . 1 . .
H H8 0.6440 0.1072 0.4439 0.060 Uiso calc R 1 . .
C C9 0.7096(2) 0.24698(16) 0.49809(11) 0.0487(4) Uani d . 1 . .
H H9 0.8116 0.2920 0.5008 0.058 Uiso calc R 1 . .
C C10 0.5048(2) 0.28363(17) 0.55592(12) 0.0489(4) Uani d . 1 . .
C C11 0.4634(2) 0.37884(16) 0.62556(11) 0.0443(4) Uani d . 1 . .
C C12 0.6143(2) 0.43552(16) 0.64662(12) 0.0482(4) Uani d . 1 . .
H H12 0.7483 0.4135 0.6138 0.058 Uiso calc R 1 . .
C C13 0.5715(2) 0.52170(18) 0.71343(12) 0.0527(4) Uani d . 1 . .
H H13 0.6752 0.5579 0.7255 0.063 Uiso calc R 1 . .
C C14 0.3717(2) 0.55579(16) 0.76392(11) 0.0486(4) Uani d . 1 . .
C C15 0.2186(2) 0.50210(17) 0.74614(12) 0.0519(4) Uani d . 1 . .
H H15 0.0856 0.5244 0.7799 0.062 Uiso calc R 1 . .
C C16 0.2630(2) 0.41471(17) 0.67776(12) 0.0500(4) Uani d . 1 . .
C C17 0.1455(3) 0.6734(2) 0.88789(13) 0.0624(5) Uani d . 1 . .
H H17A 0.1109 0.5839 0.9265 0.075 Uiso calc R 1 . .
H H17B 0.0400 0.7242 0.8444 0.075 Uiso calc R 1 . .
C C18 0.1529(3) 0.7644(2) 0.95744(15) 0.0725(5) Uani d . 1 . .
H H18 0.1876 0.8539 0.9162 0.087 Uiso calc R 1 . .
C C19 0.3163(5) 0.6912(4) 1.0255(2) 0.1396(12) Uani d . 1 . .
H H19A 0.2890 0.6010 1.0647 0.209 Uiso calc R 1 . .
H H19B 0.3149 0.7519 1.0694 0.209 Uiso calc R 1 . .
H H19C 0.4495 0.6738 0.9858 0.209 Uiso calc R 1 . .
C C20 -0.0607(4) 0.8042(3) 1.01622(17) 0.0974(8) Uani d . 1 . .
H H20A -0.1597 0.8542 0.9702 0.146 Uiso calc R 1 . .
H H20B -0.0579 0.8656 1.0590 0.146 Uiso calc R 1 . .
H H20C -0.0992 0.7181 1.0565 0.146 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'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C16 O2 H2o . . 109.5 ?
C14 O3 C17 . . 118.25(13) ?
C2 C1 H1A . . 109.5 ?
C2 C1 H1B . . 109.5 ?
H1A C1 H1B . . 109.5 ?
C2 C1 H1C . . 109.5 ?
H1A C1 H1C . . 109.5 ?
H1B C1 H1C . . 109.5 ?
C7 C2 C3 . . 117.53(15) ?
C7 C2 C1 . . 121.29(16) ?
C3 C2 C1 . . 121.18(16) ?
C4 C3 C2 . . 121.64(15) ?
C4 C3 H3 . . 119.2 ?
C2 C3 H3 . . 119.2 ?
C3 C4 C5 . . 120.67(15) ?
C3 C4 H4 . . 119.7 ?
C5 C4 H4 . . 119.7 ?
C6 C5 C4 . . 117.58(14) ?
C6 C5 C8 . . 118.64(14) ?
C4 C5 C8 . . 123.78(14) ?
C7 C6 C5 . . 121.43(15) ?
C7 C6 H6 . . 119.3 ?
C5 C6 H6 . . 119.3 ?
C6 C7 C2 . . 121.14(15) ?
C6 C7 H7 . . 119.4 ?
C2 C7 H7 . . 119.4 ?
C9 C8 C5 . . 128.63(15) ?
C9 C8 H8 . . 115.7 ?
C5 C8 H8 . . 115.7 ?
C8 C9 C10 . . 120.73(14) ?
C8 C9 H9 . . 119.6 ?
C10 C9 H9 . . 119.6 ?
O1 C10 C11 . . 119.71(14) ?
O1 C10 C9 . . 119.01(14) ?
C11 C10 C9 . . 121.27(13) ?
C12 C11 C16 . . 116.67(14) ?
C12 C11 C10 . . 123.71(13) ?
C16 C11 C10 . . 119.59(13) ?
C13 C12 C11 . . 122.25(14) ?
C13 C12 H12 . . 118.9 ?
C11 C12 H12 . . 118.9 ?
C12 C13 C14 . . 119.92(14) ?
C12 C13 H13 . . 120.0 ?
C14 C13 H13 . . 120.0 ?
O3 C14 C15 . . 124.34(14) ?
O3 C14 C13 . . 115.70(14) ?
C15 C14 C13 . . 119.96(14) ?
C14 C15 C16 . . 119.85(14) ?
C14 C15 H15 . . 120.1 ?
C16 C15 H15 . . 120.1 ?
O2 C16 C15 . . 117.28(13) ?
O2 C16 C11 . . 121.36(14) ?
C15 C16 C11 . . 121.35(14) ?
O3 C17 C18 . . 109.14(15) ?
O3 C17 H17A . . 109.9 ?
C18 C17 H17A . . 109.9 ?
O3 C17 H17B . . 109.9 ?
C18 C17 H17B . . 109.9 ?
H17A C17 H17B . . 108.3 ?
C17 C18 C19 . . 111.91(17) ?
C17 C18 C20 . . 109.22(18) ?
C19 C18 C20 . . 112.0(2) ?
C17 C18 H18 . . 107.8 ?
C19 C18 H18 . . 107.8 ?
C20 C18 H18 . . 107.8 ?
C18 C19 H19A . . 109.5 ?
C18 C19 H19B . . 109.5 ?
H19A C19 H19B . . 109.5 ?
C18 C19 H19C . . 109.5 ?
H19A C19 H19C . . 109.5 ?
H19B C19 H19C . . 109.5 ?
C18 C20 H20A . . 109.5 ?
C18 C20 H20B . . 109.5 ?
H20A C20 H20B . . 109.5 ?
C18 C20 H20C . . 109.5 ?
H20A C20 H20C . . 109.5 ?
H20B C20 H20C . . 109.5 ?
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
O1 C10 . 1.2474(18) ?
O2 C16 . 1.3429(18) ?
O2 H2o . 0.8200 ?
O3 C14 . 1.3556(19) ?
O3 C17 . 1.4332(19) ?
C1 C2 . 1.506(2) ?
C1 H1A . 0.9600 ?
C1 H1B . 0.9600 ?
C1 H1C . 0.9600 ?
C2 C7 . 1.383(2) ?
C2 C3 . 1.390(2) ?
C3 C4 . 1.376(2) ?
C3 H3 . 0.9300 ?
C4 C5 . 1.393(2) ?
C4 H4 . 0.9300 ?
C5 C6 . 1.388(2) ?
C5 C8 . 1.458(2) ?
C6 C7 . 1.377(2) ?
C6 H6 . 0.9300 ?
C7 H7 . 0.9300 ?
C8 C9 . 1.325(2) ?
C8 H8 . 0.9300 ?
C9 C10 . 1.467(2) ?
C9 H9 . 0.9300 ?
C10 C11 . 1.460(2) ?
C11 C12 . 1.401(2) ?
C11 C16 . 1.410(2) ?
C12 C13 . 1.360(2) ?
C12 H12 . 0.9300 ?
C13 C14 . 1.396(2) ?
C13 H13 . 0.9300 ?
C14 C15 . 1.374(2) ?
C15 C16 . 1.386(2) ?
C15 H15 . 0.9300 ?
C17 C18 . 1.499(3) ?
C17 H17A . 0.9700 ?
C17 H17B . 0.9700 ?
C18 C19 . 1.500(3) ?
C18 C20 . 1.523(3) ?
C18 H18 . 0.9800 ?
C19 H19A . 0.9600 ?
C19 H19B . 0.9600 ?
C19 H19C . 0.9600 ?
C20 H20A . 0.9600 ?
C20 H20B . 0.9600 ?
C20 H20C . 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
O2 H2o O1 1_555 0.82 1.77 2.499(2) 148
C12 H12 O2 1_655 0.93 2.55 3.268(2) 135
C17 H17b Cg 2_666 0.97 2.82 3.705(2) 153
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
C7 C2 C3 C4 . . . . -0.1(3) ?
C1 C2 C3 C4 . . . . 179.96(15) ?
C2 C3 C4 C5 . . . . -0.7(3) ?
C3 C4 C5 C6 . . . . 0.7(2) ?
C3 C4 C5 C8 . . . . -179.25(14) ?
C4 C5 C6 C7 . . . . 0.0(2) ?
C8 C5 C6 C7 . . . . 179.92(14) ?
C5 C6 C7 C2 . . . . -0.7(2) ?
C3 C2 C7 C6 . . . . 0.7(2) ?
C1 C2 C7 C6 . . . . -179.29(15) ?
C6 C5 C8 C9 . . . . 179.72(15) ?
C4 C5 C8 C9 . . . . -0.3(3) ?
C5 C8 C9 C10 . . . . 178.15(14) ?
C8 C9 C10 O1 . . . . -6.2(2) ?
C8 C9 C10 C11 . . . . 173.89(14) ?
O1 C10 C11 C12 . . . . 176.62(15) ?
C9 C10 C11 C12 . . . . -3.5(2) ?
O1 C10 C11 C16 . . . . -1.6(2) ?
C9 C10 C11 C16 . . . . 178.27(13) ?
C16 C11 C12 C13 . . . . -0.4(2) ?
C10 C11 C12 C13 . . . . -178.68(14) ?
C11 C12 C13 C14 . . . . 0.3(2) ?
C17 O3 C14 C15 . . . . 4.8(2) ?
C17 O3 C14 C13 . . . . -175.59(14) ?
C12 C13 C14 O3 . . . . -179.59(13) ?
C12 C13 C14 C15 . . . . 0.1(2) ?
O3 C14 C15 C16 . . . . 179.37(14) ?
C13 C14 C15 C16 . . . . -0.3(2) ?
C14 C15 C16 O2 . . . . 179.65(15) ?
C14 C15 C16 C11 . . . . 0.1(2) ?
C12 C11 C16 O2 . . . . -179.30(15) ?
C10 C11 C16 O2 . . . . -0.9(2) ?
C12 C11 C16 C15 . . . . 0.2(2) ?
C10 C11 C16 C15 . . . . 178.55(14) ?
C14 O3 C17 C18 . . . . 176.86(14) ?
O3 C17 C18 C19 . . . . -58.7(2) ?
O3 C17 C18 C20 . . . . 176.68(15) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 24744748
