#------------------------------------------------------------------------------
#$Date: 2017-10-13 11:03:29 +0300 (Fri, 13 Oct 2017) $
#$Revision: 201974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/21/03/2210391.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_2210391
loop_
_publ_author_name
'Dun-Jia Wang'
'Chun-Yang Zheng'
'Ling Fan'
_publ_section_title
;
 1-(4-tert-Butylphenyl)-3-hydroxy-3-(2-naphthyl)prop-2-en-1-one
;
_journal_coeditor_code           TK2062
_journal_issue                   9
_journal_name_full               'Acta Crystallographica Section E'
_journal_page_first              o3681
_journal_page_last               o3682
_journal_paper_doi               10.1107/S1600536806029084
_journal_volume                  62
_journal_year                    2006
_chemical_formula_iupac          'C23 H22 O2'
_chemical_formula_moiety         'C23 H22 O2'
_chemical_formula_sum            'C23 H22 O2'
_chemical_formula_weight         330.41
_chemical_melting_point          340
_chemical_name_systematic
;
1-(4-tert-Butylphenyl)-3-hydroxy-3-(2-naphthyl)prop-2-en-1-one
;
_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
_cell_angle_beta                 128.605(2)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   32.490(4)
_cell_length_b                   6.2231(8)
_cell_length_c                   22.533(3)
_cell_measurement_reflns_used    3719
_cell_measurement_temperature    292(2)
_cell_measurement_theta_max      27.5
_cell_measurement_theta_min      2.3
_cell_volume                     3560.3(8)
_computing_cell_refinement       SMART
_computing_data_collection       'SMART (Bruker, 1997)'
_computing_data_reduction        'SAINT (Bruker, 1999)'
_computing_molecular_graphics    'SHELXTL (Bruker, 2001)'
_computing_publication_material  SHELXTL
_computing_structure_refinement  'SHELXL97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS97 (Sheldrick, 1997)'
_diffrn_ambient_temperature      292(2)
_diffrn_detector_area_resol_mean 0
_diffrn_measured_fraction_theta_full 0.990
_diffrn_measured_fraction_theta_max 0.990
_diffrn_measurement_device_type  'Bruker SMART CCD area-detector'
_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  0.101
_diffrn_reflns_av_sigmaI/netI    0.066
_diffrn_reflns_limit_h_max       42
_diffrn_reflns_limit_h_min       -42
_diffrn_reflns_limit_k_max       8
_diffrn_reflns_limit_k_min       -8
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -29
_diffrn_reflns_number            15619
_diffrn_reflns_theta_full        27.5
_diffrn_reflns_theta_max         27.5
_diffrn_reflns_theta_min         1.6
_diffrn_standards_decay_%        0
_diffrn_standards_interval_count 0
_diffrn_standards_interval_time  0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  0.982
_exptl_absorpt_correction_T_min  0.977
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   '(SADABS; Sheldrick, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.233
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             1408
_exptl_crystal_size_max          0.30
_exptl_crystal_size_mid          0.20
_exptl_crystal_size_min          0.20
_refine_diff_density_max         0.22
_refine_diff_density_min         -0.25
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.02
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     234
_refine_ls_number_reflns         4055
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.02
_refine_ls_R_factor_all          0.084
_refine_ls_R_factor_gt           0.061
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0858P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.150
_refine_ls_wR_factor_ref         0.164
_reflns_number_gt                2810
_reflns_number_total             4055
_reflns_threshold_expression     I>2σ(I)
_cod_data_source_file            tk2062.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        3560.2(8)
_cod_original_sg_symbol_Hall     -C2yc
_cod_original_sg_symbol_H-M      'C 2/c'
_cod_database_code               2210391
_cod_database_fobs_code          2210391
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_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
C C1 0.52312(7) 0.4576(3) 1.10587(10) 0.0696(5) Uani d . 1
H H1A 0.5044 0.3595 1.0638 0.104 Uiso calc R 1
H H1B 0.5466 0.3787 1.1523 0.104 Uiso calc R 1
H H1C 0.5430 0.5559 1.0998 0.104 Uiso calc R 1
C C2 0.51384(10) 0.7495(3) 1.17197(11) 0.0873(6) Uani d . 1
H H2A 0.5337 0.8401 1.1637 0.131 Uiso calc R 1
H H2B 0.5374 0.6774 1.2199 0.131 Uiso calc R 1
H H2C 0.4894 0.8354 1.1723 0.131 Uiso calc R 1
C C3 0.45729(8) 0.4263(4) 1.12740(11) 0.0822(6) Uani d . 1
H H3A 0.4314 0.5008 1.1273 0.123 Uiso calc R 1
H H3B 0.4833 0.3649 1.1766 0.123 Uiso calc R 1
H H3C 0.4405 0.3140 1.0900 0.123 Uiso calc R 1
C C4 0.48372(6) 0.5837(2) 1.10864(8) 0.0491(4) Uani d . 1
C C5 0.44385(5) 0.6886(2) 1.03080(8) 0.0439(4) Uani d . 1
C C6 0.45241(6) 0.8920(3) 1.01503(9) 0.0568(4) Uani d . 1
H H6 0.4822 0.9680 1.0535 0.068 Uiso calc R 1
C C7 0.41851(7) 0.9846(3) 0.94476(10) 0.0564(4) Uani d . 1
H H7 0.4256 1.1218 0.9368 0.068 Uiso calc R 1
C C8 0.37382(6) 0.8770(2) 0.88524(8) 0.0446(4) Uani d . 1
C C9 0.36475(6) 0.6735(2) 0.90011(9) 0.0498(4) Uani d . 1
H H9 0.3352 0.5970 0.8613 0.060 Uiso calc R 1
C C10 0.39852(6) 0.5827(2) 0.97099(9) 0.0501(4) Uani d . 1
H H10 0.3909 0.4471 0.9793 0.060 Uiso calc R 1
C C11 0.33878(6) 0.9834(2) 0.81039(9) 0.0511(4) Uani d . 1
C C12 0.29937(6) 0.8765(2) 0.74332(8) 0.0499(4) Uani d . 1
H H12 0.2915 0.7342 0.7453 0.060 Uiso calc R 1
C C13 0.27165(6) 0.9808(2) 0.67346(9) 0.0495(4) Uani d . 1
C C14 0.23474(6) 0.8707(2) 0.59985(8) 0.0464(4) Uani d . 1
C C15 0.22066(6) 0.9705(2) 0.53512(9) 0.0471(4) Uani d . 1
H H15 0.2334 1.1078 0.5388 0.057 Uiso calc R 1
C C16 0.18753(5) 0.8710(2) 0.46341(9) 0.0457(4) Uani d . 1
C C17 0.17393(6) 0.9710(3) 0.39697(9) 0.0552(4) Uani d . 1
H H17 0.1870 1.1071 0.4000 0.066 Uiso calc R 1
C C18 0.14204(7) 0.8701(3) 0.32876(10) 0.0646(5) Uani d . 1
H H18 0.1334 0.9374 0.2854 0.078 Uiso calc R 1
C C19 0.12221(7) 0.6662(3) 0.32332(11) 0.0688(5) Uani d . 1
H H19 0.1004 0.5990 0.2762 0.083 Uiso calc R 1
C C20 0.13420(7) 0.5642(3) 0.38552(10) 0.0632(5) Uani d . 1
H H20 0.1205 0.4282 0.3807 0.076 Uiso calc R 1
C C21 0.16757(6) 0.6639(2) 0.45815(9) 0.0498(4) Uani d . 1
C C22 0.18168(6) 0.5647(2) 0.52489(10) 0.0570(4) Uani d . 1
H H22 0.1684 0.4293 0.5219 0.068 Uiso calc R 1
C C23 0.21432(6) 0.6635(3) 0.59342(9) 0.0536(4) Uani d . 1
H H23 0.2234 0.5941 0.6367 0.064 Uiso calc R 1
O O1 0.34739(6) 1.18445(18) 0.80858(7) 0.0758(4) Uani d . 1
H H1 0.3119(10) 1.224(4) 0.7329(14) 0.137(9) Uiso d . 1
O O2 0.27924(5) 1.18291(17) 0.67066(7) 0.0710(4) Uani d . 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
_geom_angle_publ_flag
C4 C1 H1A 109.5 ?
C4 C1 H1B 109.5 ?
H1A C1 H1B 109.5 ?
C4 C1 H1C 109.5 ?
H1A C1 H1C 109.5 ?
H1B C1 H1C 109.5 ?
C4 C2 H2A 109.5 ?
C4 C2 H2B 109.5 ?
H2A C2 H2B 109.5 ?
C4 C2 H2C 109.5 ?
H2A C2 H2C 109.5 ?
H2B C2 H2C 109.5 ?
C4 C3 H3A 109.5 ?
C4 C3 H3B 109.5 ?
H3A C3 H3B 109.5 ?
C4 C3 H3C 109.5 ?
H3A C3 H3C 109.5 ?
H3B C3 H3C 109.5 ?
C2 C4 C3 108.61(15) ?
C2 C4 C5 112.02(14) ?
C3 C4 C5 111.76(13) ?
C2 C4 C1 108.65(15) ?
C3 C4 C1 108.09(15) ?
C5 C4 C1 107.59(12) ?
C6 C5 C10 116.30(14) ?
C6 C5 C4 121.33(13) ?
C10 C5 C4 122.29(13) ?
C7 C6 C5 122.30(15) ?
C7 C6 H6 118.9 ?
C5 C6 H6 118.9 ?
C6 C7 C8 121.05(14) ?
C6 C7 H7 119.5 ?
C8 C7 H7 119.5 ?
C7 C8 C9 117.32(14) ?
C7 C8 C11 118.89(14) ?
C9 C8 C11 123.79(14) ?
C10 C9 C8 121.35(14) ?
C10 C9 H9 119.3 ?
C8 C9 H9 119.3 ?
C9 C10 C5 121.67(14) ?
C9 C10 H10 119.2 ?
C5 C10 H10 119.2 ?
O1 C11 C12 119.92(14) y
O1 C11 C8 116.34(14) ?
C12 C11 C8 123.69(14) ?
C11 C12 C13 120.70(14) y
C13 C12 H12 119.7 ?
C11 C12 H12 119.7 ?
O2 C13 C12 120.04(15) y
O2 C13 C14 116.33(14) ?
C12 C13 C14 123.58(14) ?
C15 C14 C23 118.59(15) ?
C15 C14 C13 118.82(14) ?
C23 C14 C13 122.57(14) ?
C14 C15 C16 121.94(14) ?
C14 C15 H15 119.0 ?
C16 C15 H15 119.0 ?
C15 C16 C17 122.13(14) ?
C15 C16 C21 118.64(14) ?
C17 C16 C21 119.23(15) ?
C18 C17 C16 120.59(16) ?
C18 C17 H17 119.7 ?
C16 C17 H17 119.7 ?
C17 C18 C19 120.35(17) ?
C17 C18 H18 119.8 ?
C19 C18 H18 119.8 ?
C20 C19 C18 121.11(17) ?
C20 C19 H19 119.4 ?
C18 C19 H19 119.4 ?
C19 C20 C21 120.40(16) ?
C19 C20 H20 119.8 ?
C21 C20 H20 119.8 ?
C22 C21 C16 118.81(15) ?
C22 C21 C20 122.88(15) ?
C16 C21 C20 118.31(15) ?
C23 C22 C21 121.19(14) ?
C23 C22 H22 119.4 ?
C21 C22 H22 119.4 ?
C22 C23 C14 120.82(15) ?
C22 C23 H23 119.6 ?
C14 C23 H23 119.6 ?
C11 O1 H1 100.7(12) ?
C13 O2 H1 102.6(14) ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
C1 C4 1.536(2) ?
C1 H1A 0.9600 ?
C1 H1B 0.9600 ?
C1 H1C 0.9600 ?
C2 C4 1.522(2) ?
C2 H2A 0.9600 ?
C2 H2B 0.9600 ?
C2 H2C 0.9600 ?
C3 C4 1.526(2) ?
C3 H3A 0.9600 ?
C3 H3B 0.9600 ?
C3 H3C 0.9600 ?
C4 C5 1.531(2) ?
C5 C6 1.389(2) ?
C5 C10 1.394(2) ?
C6 C7 1.370(2) ?
C6 H6 0.9300 ?
C7 C8 1.388(2) ?
C7 H7 0.9300 ?
C8 C9 1.388(2) ?
C8 C11 1.478(2) ?
C9 C10 1.374(2) ?
C9 H9 0.9300 ?
C10 H10 0.9300 ?
O1 C11 1.2881(19) y
O2 C13 1.2908(18) y
C11 C12 1.397(2) y
C12 C13 1.393(2) y
C12 H12 0.9300 ?
C13 C14 1.475(2) ?
C14 C15 1.375(2) ?
C14 C23 1.416(2) ?
C15 C16 1.408(2) ?
C15 H15 0.9300 ?
C16 C17 1.414(2) ?
C16 C21 1.414(2) ?
C17 C18 1.357(2) ?
C17 H17 0.9300 ?
C18 C19 1.393(3) ?
C18 H18 0.9300 ?
C19 C20 1.356(3) ?
C19 H19 0.9300 ?
C20 C21 1.423(2) ?
C20 H20 0.9300 ?
C21 C22 1.411(2) ?
C22 C23 1.358(2) ?
C22 H22 0.9300 ?
C23 H23 0.9300 ?
O1 H1 1.36(3) ?
O2 H1 1.14(3) ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
O2 H1 O1 1.14(3) 1.36(3) 2.4441(17) 156(2)
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
C2 C4 C5 C6 29.8(2) ?
C3 C4 C5 C6 151.98(16) ?
C1 C4 C5 C6 -89.52(18) ?
C2 C4 C5 C10 -153.33(16) ?
C3 C4 C5 C10 -31.2(2) ?
C1 C4 C5 C10 87.32(17) ?
C10 C5 C6 C7 -0.2(2) ?
C4 C5 C6 C7 176.85(14) ?
C5 C6 C7 C8 -0.7(3) ?
C6 C7 C8 C9 0.6(2) ?
C6 C7 C8 C11 -179.50(14) ?
C7 C8 C9 C10 0.3(2) ?
C11 C8 C9 C10 -179.60(14) ?
C8 C9 C10 C5 -1.2(2) ?
C6 C5 C10 C9 1.1(2) ?
C4 C5 C10 C9 -175.91(13) ?
C7 C8 C11 O1 -11.3(2) ?
C9 C8 C11 O1 168.62(15) ?
C7 C8 C11 C12 166.22(14) ?
C9 C8 C11 C12 -13.9(2) ?
O1 C11 C12 C13 4.6(2) y
C8 C11 C12 C13 -172.79(13) ?
C11 C12 C13 O2 -5.6(2) y
C11 C12 C13 C14 171.52(13) ?
O2 C13 C14 C15 15.0(2) ?
C12 C13 C14 C15 -162.25(14) ?
O2 C13 C14 C23 -166.84(14) ?
C12 C13 C14 C23 15.9(2) ?
C23 C14 C15 C16 -1.2(2) ?
C13 C14 C15 C16 177.07(12) ?
C14 C15 C16 C17 -178.51(13) ?
C14 C15 C16 C21 1.1(2) ?
C15 C16 C17 C18 179.75(14) ?
C21 C16 C17 C18 0.1(2) ?
C16 C17 C18 C19 0.0(2) ?
C17 C18 C19 C20 0.0(3) ?
C18 C19 C20 C21 -0.1(3) ?
C15 C16 C21 C22 -0.1(2) ?
C17 C16 C21 C22 179.54(14) ?
C15 C16 C21 C20 -179.86(13) ?
C17 C16 C21 C20 -0.2(2) ?
C19 C20 C21 C22 -179.54(16) ?
C19 C20 C21 C16 0.2(2) ?
C16 C21 C22 C23 -0.8(2) ?
C20 C21 C22 C23 178.90(14) ?
C21 C22 C23 C14 0.8(2) ?
C15 C14 C23 C22 0.2(2) ?
C13 C14 C23 C22 -177.98(14) ?
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 ChemSpider 30655042
