#------------------------------------------------------------------------------
#$Date: 2016-02-14 06:40:26 +0200 (Sun, 14 Feb 2016) $
#$Revision: 176432 $
#$URL: svn://www.crystallography.net/cod/cif/2/00/60/2006076.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_2006076
loop_
_publ_author_name
'Malpezzi, L.'
'Fuganti, C.'
'Grasselli, P.'
_publ_section_title
;
 Disorder in 13-cis-Retinoic Acid
;
_journal_issue                   4
_journal_name_full               'Acta Crystallographica Section C'
_journal_page_first              508
_journal_page_last               511
_journal_paper_doi               10.1107/S0108270196014588
_journal_volume                  53
_journal_year                    1997
_chemical_formula_moiety         'C20 H28 O2'
_chemical_formula_sum            'C20 H28 O2'
_chemical_formula_weight         300.42
_chemical_name_common            isotretinoin
_chemical_name_systematic        '13-cis-retinoic acid'
_space_group_IT_number           64
_symmetry_cell_setting           orthorhombic
_symmetry_space_group_name_Hall  '-C 2ac 2'
_symmetry_space_group_name_H-M   'C m c a'
_audit_creation_method           SHELXL
_cell_angle_alpha                90.00
_cell_angle_beta                 90.00
_cell_angle_gamma                90.00
_cell_formula_units_Z            8
_cell_length_a                   7.170(1)
_cell_length_b                   30.766(1)
_cell_length_c                   16.910(1)
_cell_measurement_reflns_used    40
_cell_measurement_temperature    293(2)
_cell_measurement_theta_max      38
_cell_measurement_theta_min      18
_cell_volume                     3730.2(6)
_computing_cell_refinement       'XSCANS (Siemens, 1992)'
_computing_data_reduction        XSCANS
_computing_molecular_graphics    'SHELXTL/PC (Sheldrick, 1990)'
_computing_publication_material  SHELXL93
_computing_structure_refinement  'SHELXL93 (Sheldrick, 1993)'
_computing_structure_solution    'SIR92 (Altomare et al., 1994)'
_diffrn_ambient_temperature      293(2)
_diffrn_measurement_device       'Siemens P4'
_diffrn_measurement_method       θ/2θ
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           CuK\a
_diffrn_radiation_wavelength     1.54178
_diffrn_reflns_av_R_equivalents  0.0307
_diffrn_reflns_av_sigmaI/netI    0.0220
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -33
_diffrn_reflns_limit_l_max       1
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            2963
_diffrn_reflns_theta_max         56.73
_diffrn_reflns_theta_min         2.87
_diffrn_standards_decay_%        <0.5
_diffrn_standards_interval_count 100
_diffrn_standards_number         3
_exptl_absorpt_coefficient_mu    0.520
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            orange
_exptl_crystal_density_diffrn    1.070
_exptl_crystal_density_meas      ?
_exptl_crystal_description       irregular
_exptl_crystal_F_000             1312
_exptl_crystal_size_max          0.5
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.3
_refine_diff_density_max         0.144
_refine_diff_density_min         -0.196
_refine_ls_extinction_coef       0.0049(4)
_refine_ls_extinction_method     SHELXL
_refine_ls_goodness_of_fit_all   1.043
_refine_ls_goodness_of_fit_obs   1.072
_refine_ls_hydrogen_treatment    'see experimental'
_refine_ls_matrix_type           full
_refine_ls_number_parameters     167
_refine_ls_number_reflns         1365
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.059
_refine_ls_restrained_S_obs      1.072
_refine_ls_R_factor_all          0.0555
_refine_ls_R_factor_obs          0.0449
_refine_ls_shift/esd_max         0.080
_refine_ls_shift/esd_mean        0.016
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0770P)²+0.9186P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_all         0.1330
_refine_ls_wR_factor_obs         0.1216
_reflns_number_observed          1139
_reflns_number_total             1367
_reflns_observed_criterion       >2sigma(I)
_cod_data_source_file            na1267.cif
_cod_data_source_block           55aceo
_cod_depositor_comments
;
The following automatic conversions were performed:

'_exptl_crystal_density_meas' value 'none' was changed to '?' - the
value is perceived as not measured.

Automatic conversion script
Id: cif_fix_values 3008 2015-01-20 13:52:24Z robertas 

The following automatic conversions were performed:

'_refine_ls_weighting_scheme' value 'calc
w=1/[\s^2^(Fo^2^)+(0.0770P)^2^+0.9186P] where P=(Fo^2^+2Fc^2^)/3' was
changed to 'calc'. New tag '_refine_ls_weighting_details' was
created. The value of the new tag was set to
'w=1/[\s^2^(Fo^2^)+(0.0770P)^2^+0.9186P] where P=(Fo^2^+2Fc^2^)/3'.

Automatic conversion script
Id: cif_fix_values 3143 2015-03-26 13:38:13Z robertas 
;
_cod_original_sg_symbol_Hall     '-C 2bc 2'
_cod_database_code               2006076
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'x, -y, -z'
'x, -y+1/2, z+1/2'
'x, y+1/2, -z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, -z'
'x+1/2, -y+1, z+1/2'
'x+1/2, y+1, -z+1/2'
'-x, -y, -z'
'-x, y, z'
'-x, y-1/2, -z-1/2'
'-x, -y-1/2, z-1/2'
'-x+1/2, -y+1/2, -z'
'-x+1/2, y+1/2, z'
'-x+1/2, y, -z-1/2'
'-x+1/2, -y, z-1/2'
loop_
_atom_site_label
_atom_site_occupancy
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_thermal_displace_type
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_type_symbol
O1 0.50 -0.0245(30) 0.52660(6) 0.09332(12) 0.097(3) Uani d P O
H1O 0.50 -0.0528(43) 0.5313(8) 0.0350(19) 0.072(10) Uiso d P H
O2 0.50 0.0315(24) 0.45848(6) 0.05958(11) 0.082(3) Uani d P O
C1 0.50 -0.0312(26) 0.16009(11) 0.0555(2) 0.074(4) Uani d P C
C16 0.50 0.1523(16) 0.1760(3) 0.0188(6) 0.104(3) Uani d P C
H161 0.50 0.1321(16) 0.1772(3) -0.0442(6) 0.175(18) Uiso d PR H
H162 0.50 0.1859(16) 0.2079(3) 0.0410(6) 0.175(18) Uiso d PR H
H163 0.50 0.2644(16) 0.1542(3) 0.0325(6) 0.143(6) Uiso d PR H
C17 0.50 -0.1927(17) 0.1896(3) 0.0287(6) 0.090(2) Uani d P C
H171 0.50 -0.2100(17) 0.1907(3) -0.0304(6) 0.127(6) Uiso d PR H
H172 0.50 -0.1605(17) 0.2186(3) 0.0487(6) 0.143(6) Uiso d PR H
H173 0.50 -0.3112(17) 0.1794(3) 0.0543(6) 0.127(6) Uiso d PR H
C2 0.50 -0.0749(7) 0.11510(12) 0.0225(2) 0.115(2) Uani d P C
H21 0.50 -0.2111(7) 0.10738(12) 0.0353(2) 0.102(5) Uiso d PR H
H22 0.50 -0.0644(7) 0.11549(12) -0.0366(2) 0.102(5) Uiso d PR H
C3 0.50 0.0502(16) 0.08002(13) 0.0569(2) 0.119(5) Uani d P C
H31 0.50 0.1712(16) 0.08713(13) 0.0500(2) 0.127(6) Uiso d PR H
H32 0.50 0.0294(16) 0.05437(13) 0.0329(2) 0.143(6) Uiso d PR H
C4 1 0.0000 0.07737(8) 0.1451(2) 0.0911(9) Uani d S C
H41 0.40 -0.1285 0.06382(8) 0.1507(2) 0.083(14) Uiso d PR H
H42 0.50 0.0925 0.05772(8) 0.1730(2) 0.102(5) Uiso d PR H
C5 1 0.0000 0.12094(7) 0.18474(14) 0.0631(6) Uani d S C
C18 1 0.0000 0.11788(8) 0.27425(14) 0.0775(8) Uani d S C
H181 1 -0.1140 0.13213(8) 0.29778(14) 0.143(6) Uiso d R H
H182 1 0.0000 0.08988(8) 0.28980(14) 0.143(6) Uiso d SR H
C6 1 0.0000 0.15917(7) 0.14531(13) 0.0620(6) Uani d S C
C7 1 0.0000 0.19922(7) 0.19080(12) 0.0591(6) Uani d S C
H7 1 0.0000 0.19489(7) 0.24830(12) 0.069(3) Uiso d SR H
C8 1 0.0000 0.24081(7) 0.16857(13) 0.0585(6) Uani d S C
H8 1 0.0000 0.24645(7) 0.11328(13) 0.069(3) Uiso d SR H
C9 1 0.0000 0.27811(6) 0.22047(12) 0.0550(6) Uani d S C
C10 1 0.0000 0.31845(7) 0.18868(13) 0.0596(6) Uani d S C
H10 1 0.0000 0.32004(7) 0.12850(13) 0.069(3) Uiso d SR H
C11 1 0.0000 0.35904(7) 0.22948(13) 0.0602(6) Uani d S C
H11 1 0.0000 0.35848(7) 0.28761(13) 0.069(3) Uiso d SR H
C12 1 0.0000 0.39791(7) 0.19357(13) 0.0611(6) Uani d S C
H12 1 0.0000 0.39813(7) 0.13617(13) 0.069(3) Uiso d SR H
C13 1 0.0000 0.43948(7) 0.23327(12) 0.0617(6) Uani d S C
C14 1 0.0000 0.47803(7) 0.19530(13) 0.0683(7) Uani d S C
H14 1 0.0000 0.50251(7) 0.22710(13) 0.069(3) Uiso d SR H
C15 1 0.0000 0.48583(7) 0.11086(14) 0.0690(7) Uani d S C
C19 1 0.0000 0.27061(7) 0.30828(13) 0.0651(7) Uani d S C
H191 1 0.0000 0.29595(7) 0.33779(13) 0.127(6) Uiso d SR H
H192 1 -0.1145 0.25521(7) 0.32720(13) 0.127(6) Uiso d R H
C20 1 0.0000 0.43958(8) 0.32245(13) 0.0753(8) Uani d S C
H201 1 0.1177 0.42281(8) 0.34213(13) 0.102(5) Uiso d R H
H203 1 0.0000 0.46096(8) 0.34050(13) 0.143(6) Uiso d SR H
loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0181 0.0091 '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 0.0492 0.0322 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
O1 O1 C15 10 . 82.2(9) ?
O2 O2 C15 10 . 79.4(8) ?
C1 C1 C16 10 10 137.7(8) ?
C1 C1 C2 10 . 101.9(7) ?
C16 C1 C2 10 . 91.9(9) ?
C1 C1 C16 10 . 31.0(6) ?
C16 C1 C16 10 . 106.7(10) ?
C2 C1 C16 . . 108.6(8) ?
C1 C1 C6 10 . 81.6(7) ?
C16 C1 C6 10 . 129.6(11) ?
C2 C1 C6 . . 112.0(3) yes
C16 C1 C6 . . 106.3(10) ?
C1 C1 C17 10 . 138.8(7) ?
C16 C1 C17 10 . 16.7(7) ?
C2 C1 C17 . . 105.9(10) ?
C16 C1 C17 . . 109.7(3) ?
C6 C1 C17 . . 114.3(7) ?
C1 C1 C2 10 10 63.0(6) ?
C16 C1 C2 10 10 120.3(6) ?
C2 C1 C2 . 10 38.9(4) ?
C16 C1 C2 . 10 74.9(8) ?
C6 C1 C2 . 10 104.3(6) ?
C17 C1 C2 . 10 137.0(6) ?
C1 C1 C17 10 10 32.3(5) ?
C16 C1 C17 10 10 107.4(5) ?
C2 C1 C17 . 10 121.4(8) ?
C16 C1 C17 . 10 13.2(6) ?
C6 C1 C17 . 10 97.0(8) ?
C17 C1 C17 . 10 106.4(9) ?
C2 C1 C17 10 10 86.1(8) ?
C17 C16 C1 10 10 124.(2) ?
C17 C16 C1 10 . 126.(2) ?
C1 C16 C1 10 . 11.3(10) ?
C17 C16 C2 10 10 153.(3) ?
C1 C16 C2 10 10 51.2(4) ?
C1 C16 C2 . 10 55.8(4) ?
C16 C17 C1 10 . 39.2(19) ?
C16 C17 C1 10 10 41.(2) ?
C1 C17 C1 . 10 8.9(8) ?
C2 C2 C3 10 10 81.8(6) ?
C2 C2 C3 10 . 53.8(4) ?
C3 C2 C3 10 . 28.0(9) ?
C2 C2 C1 10 . 78.1(7) ?
C3 C2 C1 10 . 126.1(5) ?
C3 C2 C1 . . 112.5(6) yes
C2 C2 C1 10 10 63.0(6) ?
C3 C2 C1 10 10 119.9(5) ?
C3 C2 C1 . 10 101.0(6) ?
C1 C2 C1 . 10 15.1(12) ?
C2 C2 C16 10 10 106.5(4) ?
C3 C2 C16 10 10 153.0(5) ?
C3 C2 C16 . 10 149.4(5) ?
C1 C2 C16 . 10 36.9(6) ?
C1 C2 C16 10 10 49.3(6) ?
C3 C3 C2 10 10 98.2(6) ?
C3 C3 C2 10 . 53.8(4) ?
C2 C3 C2 10 . 44.4(5) ?
C3 C3 C4 10 . 76.5(4) ?
C2 C3 C4 10 . 122.4(3) ?
C2 C3 C4 . . 105.7(5) yes
C5 C4 C3 . 10 112.7(2) ?
C5 C4 C3 . . 112.7(2) yes
C3 C4 C3 10 . 27.1(8) ?
C6 C5 C4 . . 123.9(2) yes
C6 C5 C18 . . 123.1(2) ?
C4 C5 C18 . . 113.0(2) ?
C5 C6 C7 . . 118.5(2) yes
C5 C6 C1 . . 120.3(2) yes
C7 C6 C1 . . 120.5(2) yes
C5 C6 C1 . 10 120.3(2) ?
C7 C6 C1 . 10 120.5(2) ?
C1 C6 C1 . 10 16.8(14) ?
C8 C7 C6 . . 131.7(2) yes
C7 C8 C9 . . 126.2(2) yes
C10 C9 C8 . . 119.2(2) yes
C10 C9 C19 . . 122.2(2) yes
C8 C9 C19 . . 118.6(2) yes
C9 C10 C11 . . 127.7(2) yes
C12 C11 C10 . . 124.2(2) yes
C11 C12 C13 . . 125.4(2) yes
C14 C13 C12 . . 123.9(2) yes
C14 C13 C20 . . 118.3(2) yes
C12 C13 C20 . . 117.8(2) yes
C13 C14 C15 . . 128.0(2) yes
O2 C15 O2 10 . 21.2(16) ?
O2 C15 O1 10 10 121.6(2) ?
O2 C15 O1 . 10 118.3(4) ?
O2 C15 O1 10 . 118.3(4) ?
O2 C15 O1 . . 121.6(2) yes
O1 C15 O1 10 . 15.5(19) ?
O2 C15 C14 10 . 125.6(2) ?
O2 C15 C14 . . 125.6(2) yes
O1 C15 C14 10 . 112.6(2) ?
O1 C15 C14 . . 112.6(2) yes
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 O1 10 0.35(4) ?
O1 C15 . 1.301(4) yes
O2 O2 10 0.45(3) ?
O2 C15 . 1.229(4) yes
C1 C1 10 0.45(4) ?
C1 C16 10 1.17(2) ?
C1 C2 . 1.525(6) yes
C1 C16 . 1.54(2) ?
C1 C6 . 1.535(5) yes
C1 C17 . 1.54(2) ?
C1 C2 10 1.675(10) ?
C1 C17 10 1.90(2) ?
C16 C17 10 0.54(2) ?
C16 C1 10 1.17(2) ?
C16 C2 10 1.956(10) ?
C17 C16 10 0.54(2) ?
C17 C1 10 1.90(2) ?
C2 C2 10 1.075(10) ?
C2 C3 10 1.239(5) ?
C2 C3 . 1.519(8) yes
C2 C1 10 1.675(10) ?
C2 C16 10 1.956(10) ?
C3 C3 10 0.72(2) ?
C3 C2 10 1.239(5) ?
C3 C4 . 1.537(6) yes
C4 C5 . 1.498(3) yes
C4 C3 10 1.537(6) ?
C5 C6 . 1.352(3) yes
C5 C18 . 1.517(3) ?
C6 C7 . 1.453(3) yes
C6 C1 10 1.535(5) ?
C7 C8 . 1.334(3) yes
C8 C9 . 1.445(3) yes
C9 C10 . 1.353(3) yes
C9 C19 . 1.503(3) ?
C10 C11 . 1.427(3) yes
C11 C12 . 1.341(3) yes
C12 C13 . 1.445(3) yes
C13 C14 . 1.349(3) yes
C13 C20 . 1.508(3) ?
C14 C15 . 1.448(3) yes
C15 O2 10 1.229(4) ?
C15 O1 10 1.301(4) ?
loop_
_geom_contact_atom_site_label_1
_geom_contact_atom_site_label_2
_geom_contact_distance
_geom_contact_site_symmetry_2
H(8) H(171) 1.802 .
H(8) H(161) 2.163 .
H(8) H(10) 2.28 .
H(7) H(181) 2.26 .
H(7) H(192) 2.43 .
H(10) H(12) 2.41 .
H(11) H(191) 2.10 .
H(11) H(201) 2.34 .
H(12) O(2) 2.27 .
H(14) H(202) 2.30 .
H(31) O(1)^i^ 2.961 5_545
H(41) O(1)^ii^ 2.906 14_455
H(182) O(2)^iii^ 2.780 11_556
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
C6 C5 C4 C3 . . . . 14.7(4) yes
C5 C4 C3 C2 . . . . -50.1(6) yes
C4 C3 C2 C1 . . . . 65.9(8) yes
C3 C2 C1 C6 . . . . -43.5(13) yes
C5 C6 C1 C2 . . . . 4.6(14) yes
C6 C5 C4 C3 . . . 10 -14.7(4) ?
C5 C4 C3 C2 . . 10 10 50.1(6) ?
C4 C3 C2 C1 . 10 10 10 -65.9(8) ?
C3 C2 C1 C6 10 10 10 . 43.5(13) ?
C1 C6 C7 C8 . . . . -9.7(8) yes
C1 C6 C7 C8 10 . . . 9.7(8) ?
C18 C5 C6 C7 . . . . 0.0 ?
C13 C14 C15 O1 . . . . 171.6(10) yes
C13 C14 C15 O1 . . . 10 -171.6(10) ?
