#------------------------------------------------------------------------------
#$Date: 2016-02-14 16:26:36 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176435 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/16/2001629.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_2001629
loop_
_publ_author_name
'Ravikumar, K.'
_publ_section_title
;
 Non-steroidal anti-inflammatory drugs. II. Structure of
 (E)-2,6-di-tert-butyl-4-[2-(4-fluorophenyl)ethenyl]phenol
;
_journal_issue                   6
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              1180
_journal_page_last               1182
_journal_paper_doi               10.1107/S0108270192013076
_journal_volume                  49
_journal_year                    1993
_chemical_formula_sum            'C22 H27 F O'
_chemical_formula_weight         326.4
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_type_scat_source           'SHELXTL-Plus (Sheldrick, 1990)'
_cell_angle_alpha                90.
_cell_angle_beta                 90.49(2)
_cell_angle_gamma                90.
_cell_formula_units_Z            4
_cell_length_a                   11.9410(10)
_cell_length_b                   18.423(2)
_cell_length_c                   8.7910(10)
_cell_measurement_reflns_used    25
_cell_measurement_temperature    294
_cell_measurement_theta_max      25
_cell_measurement_theta_min      15
_cell_volume                     1933.9(3)
_computing_cell_refinement       'Siemens R3m/V software'
_computing_data_collection       'Siemens R3m/V software'
_computing_molecular_graphics
'SHELXTL-Plus. Computer: VAX 3100 workstation'
_computing_structure_refinement
;
SHELXTL-Plus. Program(s) used for geometrical calculations including
 crystal packing: PARST (Nardelli, 1983)
;
_computing_structure_solution    'SHELXTL-Plus (Sheldrick, 1990)'
_diffrn_measurement_device       'Siemens R3m/V'
_diffrn_measurement_method       ω/2θ
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71063
_diffrn_reflns_av_R_equivalents  0.063
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       0
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       0
_diffrn_reflns_number            2845
_diffrn_reflns_theta_max         22.5
_diffrn_standards_decay_%        1
_diffrn_standards_interval_count 98
_diffrn_standards_number         2
_exptl_absorpt_coefficient_mu    0.069
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            'Pale orange'
_exptl_crystal_density_diffrn    1.12
_exptl_crystal_density_meas      1.09
_exptl_crystal_density_method    'flotation in aqueous KI solution'
_exptl_crystal_description       Cube
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.19
_exptl_crystal_size_min          0.15
_refine_diff_density_max         0.20
_refine_diff_density_min         -0.21
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_obs   1.02
_refine_ls_hydrogen_treatment
;H atoms placed in calculated positions and allowed to ride
on the parent C atoms
;
_refine_ls_number_parameters     217
_refine_ls_number_reflns         1331
_refine_ls_R_factor_obs          0.047
_refine_ls_shift/esd_max         0.05
_refine_ls_structure_factor_coef F
_refine_ls_weighting_details     w=[σ²(F)+0.00076F²]⁻¹
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_obs         0.049
_reflns_number_observed          1331
_reflns_number_total             2543
_reflns_observed_criterion       I>=3\s(I)
_cod_data_source_file            ha1029.cif
_cod_data_source_block           ha1029_structure_1_of_1
_cod_depositor_comments
;
The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'w=[\s^2^(F)+0.00076F^2^]^-1^'
was changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to
'w=[\s^2^(F)+0.00076F^2^]^-1^'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_cell_volume        1933.8(3)
_cod_original_formula_sum        'C22 H27 F1 O1'
_cod_database_code               2001629
loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
F(1) .7003(4) .3384(3) 1.1848(5) 113(2)
O(1) .0795(4) .4959(3) .1403(5) 68(2)
C(1) .6386(5) .3519(4) 1.0561(5) 67(2)
C(2) .5873(4) .2954(4) .9861(4) 63(2)
C(3) .5252(5) .3072(4) .8561(5) 54(2)
C(4) .5124(4) .3759(4) .7963(5) 47(2)
C(5) .5692(5) .4330(4) .8691(5) 59(2)
C(6) .6320(5) .4210(4) 1.0017(5) 66(3)
C(7) .4401(5) .3878(4) .6600(5) 50(2)
C(8) .3995(5) .4487(4) .6109(6) 54(2)
C(9) .3181(5) .4606(3) .4833(5) 43(2)
C(10) .2590(4) .5248(3) .4756(5) 46(2)
C(11) .1768(4) .5394(3) .3642(5) 39(2)
C(12) .1596(4) .4846(3) .2545(5) 41(2)
C(13) .2175(4) .4190(3) .2554(5) 44(2)
C(14) .2970(4) .4092(3) .3722(5) 45(2)
C(15) .1944(5) .3598(3) .1339(5) 54(2)
C(16) .2197(5) .3887(4) -.0253(5) 71(3)
C(17) .2715(6) .2936(4) .1571(6) 76(3)
C(18) .0733(5) .3339(5) .1436(6) 80(3)
C(19) .1097(5) .6105(3) .3650(5) 47(2)
C(20) .1453(5) .6594(4) .4986(5) 80(3)
C(21) -.0148(5) .5968(4) .3834(5) 66(2)
C(22) .1320(6) .6553(4) .2196(5) 77(3)
H1A .07753 .45891 0.08256 ?
H2A .59517 .24751 1.02768 ?
H3A .48900 .26724 0.80560 ?
H5A .56515 .48067 0.82521 ?
H6A .66838 .46011 1.05462 ?
H7A .42123 .34589 0.59991 ?
H8A .42483 .49098 0.66481 ?
H10A .27479 .56144 0.55035 ?
H14A .33874 .36469 0.37478 ?
H16A .17340 .43001 -0.04744 ?
H16B .29702 .40277 -0.02736 ?
H16C .20633 .35162 -0.10006 ?
H17A .34811 .30891 0.14987 ?
H17B .25877 .27336 0.25616 ?
H17C .25621 .25748 0.08097 ?
H18A .02331 .37416 0.12834 ?
H18B .05896 .29766 0.06748 ?
H18C .06152 .31354 0.24267 ?
H20A .13342 .63418 0.59269 ?
H20B .22318 .67137 0.48952 ?
H20C .10156 .70313 0.49720 ?
H21A -.02692 .56946 0.47485 ?
H21B -.05443 .64200 0.38909 ?
H21C -.04160 .56951 0.29747 ?
H22A .21079 .66425 0.20980 ?
H22B .10561 .62825 0.13307 ?
H22C .09278 .70073 0.22470 ?
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
F(1) C(1) C(6) 119.3(5) yes
C(2) C(1) C(6) 122.3(4) yes
C(2) C(3) C(4) 121.2(5) yes
C(3) C(4) C(5) 117.6(5) yes
C(4) C(5) C(6) 121.0(6) yes
C(4) C(7) C(8) 127.5(5) yes
C(8) C(9) C(14) 122.8(5) yes
C(10) C(9) C(14) 117.6(5) yes
C(10) C(11) C(19) 121.4(4) yes
C(12) C(11) C(19) 122.7(4) yes
C(11) C(12) C(13) 123.2(4) yes
C(12) C(13) C(15) 121.5(5) yes
C(14) C(13) C(15) 121.9(5) yes
C(13) C(15) C(18) 110.1(4) yes
C(13) C(15) C(16) 110.5(5) yes
C(16) C(15) C(18) 110.7(4) yes
C(11) C(19) C(22) 111.0(4) yes
C(11) C(19) C(20) 111.3(4) yes
C(20) C(19) C(22) 105.7(5) yes
F(1) C(1) C(2) 118.3(5) yes
C(1) C(2) C(3) 119.7(6) yes
C(3) C(4) C(7) 120.2(6) yes
C(5) C(4) C(7) 122.2(6) yes
C(1) C(6) C(5) 118.1(6) yes
C(7) C(8) C(9) 128.1(6) yes
C(8) C(9) C(10) 119.6(5) yes
C(9) C(10) C(11) 123.5(5) yes
C(10) C(11) C(12) 115.8(5) yes
O(1) C(12) C(11) 118.7(5) yes
O(1) C(12) C(13) 118.0(4) yes
C(12) C(13) C(14) 116.6(5) yes
C(9) C(14) C(13) 123.2(5) yes
C(13) C(15) C(17) 111.3(4) yes
C(17) C(15) C(18) 108.1(5) yes
C(16) C(15) C(17) 105.9(4) yes
C(11) C(19) C(21) 111.7(5) yes
C(21) C(19) C(22) 110.7(5) yes
C(20) C(19) C(21) 106.3(4) yes
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_publ_flag
F(1) C(1) 1.367(6) yes
C(1) C(2) 1.353(8) yes
C(2) C(3) 1.375(7) yes
C(4) C(5) 1.404(9) yes
C(5) C(6) 1.398(7) yes
C(8) C(9) 1.494(7) yes
C(9) C(14) 1.383(7) yes
C(11) C(12) 1.409(7) yes
C(12) C(13) 1.393(8) yes
C(13) C(15) 1.549(8) yes
C(15) C(17) 1.541(9) yes
C(19) C(20) 1.537(8) yes
C(19) C(22) 1.547(7) yes
O(1) C(12) 1.396(6) yes
C(1) C(6) 1.361(9) yes
C(3) C(4) 1.378(9) yes
C(4) C(7) 1.487(7) yes
C(7) C(8) 1.296(9) yes
C(9) C(10) 1.378(8) yes
C(10) C(11) 1.407(7) yes
C(11) C(19) 1.536(8) yes
C(13) C(14) 1.404(7) yes
C(15) C(16) 1.530(7) yes
C(15) C(18) 1.526(9) yes
C(19) C(21) 1.518(8) yes
