#------------------------------------------------------------------------------
#$Date: 2019-11-24 15:53:59 +0200 (Sun, 24 Nov 2019) $
#$Revision: 238432 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/52/1555262.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_1555262
loop_
_publ_author_name
'Cui, Peng'
'McMahon, David P.'
'Spackman, Peter R.'
'Alston, Ben M.'
'Little, Marc A.'
'Day, Graeme M.'
'Cooper, Andrew I.'
_publ_section_title
;
 Mining predicted crystal structure landscapes with high throughput
 crystallisation: old molecules, new insights
;
_journal_issue                   43
_journal_name_full               'Chemical Science'
_journal_page_first              9988
_journal_paper_doi               10.1039/C9SC02832C
_journal_volume                  10
_journal_year                    2019
_chemical_formula_moiety         'C14 H16 O8, 0.43(C14 H30)'
_chemical_formula_sum            'C20 H28.9 O8'
_chemical_formula_weight         397.29
_space_group_crystal_system      orthorhombic
_space_group_IT_number           70
_space_group_name_Hall           '-F 2uv 2vw'
_space_group_name_H-M_alt        'F d d d :2'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-12-05
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_audit_update_record
;
2019-05-10 deposited with the CCDC.	2019-08-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   7.3713(11)
_cell_length_b                   22.951(4)
_cell_length_c                   23.585(4)
_cell_measurement_reflns_used    1322
_cell_measurement_temperature    200
_cell_measurement_theta_max      25.694
_cell_measurement_theta_min      2.477
_cell_volume                     3990.1(11)
_computing_cell_refinement       'SAINT v8.34A (Bruker, 2013)'
_computing_data_collection
'CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'XT (Sheldrick, 2015)'
_diffrn_ambient_temperature      200
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku Saturn724+'
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device       'AFC12 (Right): Kappa 3 circle'
_diffrn_measurement_device_type  'Rigaku Saturn724+ (2x2 bin mode)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_radiation_collimation    0.3
_diffrn_radiation_monochromator  Confocal
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0818
_diffrn_reflns_av_unetI/netI     0.0561
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       28
_diffrn_reflns_limit_k_min       -28
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            8009
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.377
_diffrn_reflns_theta_min         2.477
_diffrn_source                   'Rotating Anode'
_diffrn_source_current           24.0
_diffrn_source_power             1.2
_diffrn_source_target            Mo
_diffrn_source_type              'Rotating Anode'
_diffrn_source_voltage           50.0
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.102
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.4564
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2014/5 (Bruker,2014/5) was used for absorption correction. wR2(int) was 0.0979 before and 0.0743 after correction. The Ratio of minimum to maximum transmission is 0.6123. The λ/2 correction factor is 0.00150.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.323
_exptl_crystal_description       block
_exptl_crystal_F_000             1703
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.05
_refine_diff_density_max         0.332
_refine_diff_density_min         -0.260
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     67
_refine_ls_number_reflns         1028
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.044
_refine_ls_R_factor_all          0.1034
_refine_ls_R_factor_gt           0.0634
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.1230P)²+3.7672P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1830
_refine_ls_wR_factor_ref         0.2143
_reflns_Friedel_coverage         0.000
_reflns_number_gt                628
_reflns_number_total             1028
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9sc02832c2.cif
_cod_data_source_block           ADTA_3-38_ethanol-tetradecane_3-fold_publ
_cod_original_cell_volume        3990.0(11)
_cod_original_sg_symbol_H-M      'F d d d'
_cod_database_code               1555262
_shelx_shelxl_version_number     2014/7
_shelx_space_group_comment
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;
_shelx_estimated_absorpt_t_max   0.995
_shelx_estimated_absorpt_t_min   0.989
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
 At 1.5 times of:
  All O(H) groups
2. Rigid body (RIGU) restrains
 C7, C6
 with sigma for 1-2 distances of 0.002 and sigma for 1-3 distances of 0.002
3. Others
 Fixed Sof: H4A(0.5) H4B(0.5) H3A(0.5) H3B(0.5) H1A(0.5) H1B(0.5)
4.a Secondary CH2 refined with riding coordinates:
 C4(H4A,H4B), C3(H3A,H3B), C1(H1A,H1B)
4.b Idealised tetrahedral OH refined as rotating group:
 O2(H2)
;
_shelx_res_file
;
    pc_8_338_200k_fddd.res created by SHELXL-2014/7

TITL pc_8_338_200k_fddd_a.res in Fddd
REM Old TITL PC_8_338_200K_Fddd in Fddd
REM SHELXT solution in Fddd
REM R1 0.266, Rweak 0.008, Alpha 0.030, Orientation as input
REM Formula found by SHELXT: C7 O4
CELL 0.71073 7.3713 22.9506 23.5851 90 90 90
ZERR 8 0.0011 0.0038 0.0039 0 0 0
LATT 4
SYMM 0.75-X,0.75-Y,+Z
SYMM 0.75-X,+Y,0.75-Z
SYMM +X,0.75-Y,0.75-Z
SFAC C H O
UNIT 160 230.86 64
EQIV $1 -X,1-Y,1-Z
RIGU 0.002 0.002 C7 C6

L.S. 50
PLAN  20
SIZE 0.11 0.08 0.05
TEMP -73.15
HTAB O2 O1_$1
BOND $H
list 4
fmap 2
acta
REM <olex2.extras>
REM <HklSrc "%.\\PC_8_338_200K_Fddd.hkl">
REM </olex2.extras>

WGHT    0.123000    3.767200
FVAR       0.21648
O2    3    0.232440    0.486039    0.483586    11.00000    0.02813    0.06615 =
         0.06137   -0.03464    0.00230   -0.00122
AFIX 147
H2    2    0.161253    0.504428    0.504875    11.00000   -1.50000
AFIX   0
O1    3   -0.026267    0.450756    0.449972    11.00000    0.01953    0.07276 =
         0.06182   -0.03231    0.00199    0.00169
C4    1    0.375000    0.375000    0.450348    10.50000    0.01921    0.03436 =
         0.02639    0.00000    0.00000   -0.00207
AFIX  23
H4A   2    0.451662    0.399803    0.474952    10.50000   -1.20000
H4B   2    0.298337    0.350196    0.474951    10.50000   -1.20000
AFIX   0
C5    1    0.139514    0.452057    0.450237    11.00000    0.02211    0.03623 =
         0.03239   -0.00237   -0.00034   -0.00121
C2    1    0.253850    0.413628    0.412622    11.00000    0.01650    0.03290 =
         0.03223   -0.00168    0.00071    0.00070
C3    1    0.375000    0.452728    0.375000    10.50000    0.02256    0.03116 =
         0.03414    0.00000   -0.00042    0.00000
AFIX  23
H3A   2    0.451728    0.477993    0.399134    10.50000   -1.20000
H3B   2    0.298275    0.477994    0.350866    10.50000   -1.20000
AFIX   0
C1    1    0.133534    0.375000    0.375000    10.50000    0.01929    0.03211 =
         0.03021   -0.00253    0.00000    0.00000
AFIX  23
H1A   2    0.054818    0.350274    0.399037    10.50000   -1.20000
H1B   2    0.054813    0.399724    0.350963    10.50000   -1.20000
AFIX   0

C7    1    0.375000    0.375000    0.610638    10.50000    0.22734    0.15391 =
         0.11124    0.00000    0.00000   -0.04155
C6    1    0.206145    0.378764    0.646050    11.00000    0.22972    0.16679 =
         0.11996    0.03044    0.00396    0.00099
HKLF 4

REM  pc_8_338_200k_fddd_a.res in Fddd
REM R1 =  0.0634 for     628 Fo > 4sig(Fo)  and  0.1034 for all    1028 data
REM     67 parameters refined using      3 restraints

END

WGHT      0.1229      3.7791

REM Highest difference peak  0.332,  deepest hole -0.260,  1-sigma level  0.063
Q1    1   0.1751  0.3317  0.6730  11.00000  0.05    0.33
Q2    1   0.3560  0.4214  0.5783  11.00000  0.05    0.27
Q3    1   0.2662  0.4112  0.6206  11.00000  0.05    0.26
Q4    1   0.2436  0.4215  0.6796  11.00000  0.05    0.24
Q5    1   0.0011  0.4176  0.4829  11.00000  0.05    0.20
Q6    1   0.3750  0.3750  0.6851  10.50000  0.05    0.19
Q7    1   0.3139  0.4266  0.3989  11.00000  0.05    0.18
Q8    1   0.2067  0.4283  0.4245  11.00000  0.05    0.18
Q9    1   0.2796  0.4103  0.5714  11.00000  0.05    0.18
Q10   1   0.5165  0.4376  0.5680  11.00000  0.05    0.16
Q11   1   0.3217  0.4302  0.6420  11.00000  0.05    0.16
Q12   1   0.3379  0.4190  0.6516  11.00000  0.05    0.16
Q13   1   0.1559  0.4505  0.5062  11.00000  0.05    0.15
Q14   1   0.0850  0.4292  0.6495  11.00000  0.05    0.14
Q15   1   0.1277  0.4086  0.6849  11.00000  0.05    0.14
Q16   1   0.1107  0.4155  0.4893  11.00000  0.05    0.14
Q17   1   0.2890  0.3695  0.7227  11.00000  0.05    0.14
Q18   1   0.1250  0.4381  0.6250  10.50000  0.05    0.13
Q19   1   0.4763  0.4168  0.5993  11.00000  0.05    0.13
Q20   1   0.2495  0.4481  0.6420  11.00000  0.05    0.12
;
_shelx_res_checksum              26456
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+3/4, -y+3/4, z'
'-x+3/4, y, -z+3/4'
'x, -y+3/4, -z+3/4'
'x, y+1/2, z+1/2'
'-x+3/4, -y+5/4, z+1/2'
'-x+3/4, y+1/2, -z+5/4'
'x, -y+5/4, -z+5/4'
'x+1/2, y, z+1/2'
'-x+5/4, -y+3/4, z+1/2'
'-x+5/4, y, -z+5/4'
'x+1/2, -y+3/4, -z+5/4'
'x+1/2, y+1/2, z'
'-x+5/4, -y+5/4, z'
'-x+5/4, y+1/2, -z+3/4'
'x+1/2, -y+5/4, -z+3/4'
'-x, -y, -z'
'x-3/4, y-3/4, -z'
'x-3/4, -y, z-3/4'
'-x, y-3/4, z-3/4'
'-x, -y+1/2, -z+1/2'
'x-3/4, y-1/4, -z+1/2'
'x-3/4, -y+1/2, z-1/4'
'-x, y-1/4, z-1/4'
'-x+1/2, -y, -z+1/2'
'x-1/4, y-3/4, -z+1/2'
'x-1/4, -y, z-1/4'
'-x+1/2, y-3/4, z-1/4'
'-x+1/2, -y+1/2, -z'
'x-1/4, y-1/4, -z'
'x-1/4, -y+1/2, z-3/4'
'-x+1/2, y-1/4, z-3/4'
loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
O2 O 0.2324(3) 0.48604(10) 0.48359(9) 0.0519(7) Uani 1 1 d . . .
O1 O -0.0263(3) 0.45076(11) 0.44997(9) 0.0514(8) Uani 1 1 d . . .
C4 C 0.3750 0.3750 0.45035(13) 0.0267(9) Uani 1 2 d S T P
C5 C 0.1395(3) 0.45206(12) 0.45024(10) 0.0302(7) Uani 1 1 d . . .
C2 C 0.2539(3) 0.41363(11) 0.41262(9) 0.0272(7) Uani 1 1 d . . .
C3 C 0.3750 0.45273(16) 0.3750 0.0293(9) Uani 1 2 d S T P
C1 C 0.1335(5) 0.3750 0.3750 0.0272(8) Uani 1 2 d S T P
loop_
_atom_site_aniso_label
_atom_site_aniso_U_11
_atom_site_aniso_U_22
_atom_site_aniso_U_33
_atom_site_aniso_U_23
_atom_site_aniso_U_13
_atom_site_aniso_U_12
O2 0.0281(11) 0.0662(16) 0.0614(14) -0.0346(11) 0.0023(10) -0.0012(11)
O1 0.0195(11) 0.0728(17) 0.0618(14) -0.0323(12) 0.0020(9) 0.0017(10)
C4 0.0192(18) 0.034(2) 0.0264(17) 0.000 0.000 -0.0021(15)
C5 0.0221(13) 0.0362(16) 0.0324(14) -0.0024(10) -0.0003(10) -0.0012(12)
C2 0.0165(12) 0.0329(14) 0.0322(13) -0.0017(10) 0.0007(10) 0.0007(11)
C3 0.0226(18) 0.031(2) 0.0341(19) 0.000 -0.0004(14) 0.000
C1 0.0193(18) 0.0321(19) 0.0302(17) -0.0025(15) 0.000 0.000
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_site_symmetry_1
_geom_angle_site_symmetry_3
C2 C4 C2 109.5(3) 2 .
O2 C5 C2 114.3(2) . .
O1 C5 O2 122.9(3) . .
O1 C5 C2 122.8(2) . .
C4 C2 C3 109.30(16) . .
C5 C2 C4 108.70(19) . .
C5 C2 C3 108.7(2) . .
C5 C2 C1 110.8(2) . .
C1 C2 C4 109.64(17) . .
C1 C2 C3 109.69(16) . .
C2 C3 C2 109.0(3) . 3
C2 C1 C2 109.5(3) 4 .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O2 C5 1.302(3) .
O1 C5 1.222(3) .
C4 C2 1.541(3) .
C4 C2 1.541(3) 2
C5 C2 1.508(3) .
C2 C3 1.546(3) .
C2 C1 1.536(3) .
C3 C2 1.546(3) 3
C1 C2 1.536(3) 4
