#------------------------------------------------------------------------------
#$Date: 2019-11-24 15:53:59 +0200 (Sun, 24 Nov 2019) $
#$Revision: 238432 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/52/1555264.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_1555264
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            'C20.02 H28.86 O8'
_chemical_formula_weight         397.50
_space_group_crystal_system      tetragonal
_space_group_IT_number           141
_space_group_name_Hall           '-I 4bd 2'
_space_group_name_H-M_alt        'I 41/a m d :2'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_audit_creation_date             2018-12-06
_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            4
_cell_length_a                   16.429(3)
_cell_length_b                   16.429(3)
_cell_length_c                   7.3580(12)
_cell_measurement_reflns_used    2537
_cell_measurement_temperature    200
_cell_measurement_theta_max      25.936
_cell_measurement_theta_min      2.478
_cell_volume                     1986.0(6)
_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    'ShelXT (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 1.000
_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  0.0598
_diffrn_reflns_av_unetI/netI     0.0356
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -20
_diffrn_reflns_limit_k_max       19
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       6
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            7390
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.377
_diffrn_reflns_theta_min         2.479
_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  0.4644
_exptl_absorpt_process_details
;
Reflections not merged
7998 Corrected reflections written to file PC_8_638_200K_0m.hkl
Estimated minimum and maximum transmission:  0.4644  0.7454
The ratio of these values is more reliable than their absolute values!
Additional spherical absorption correction applied with mu*r =  0.2000
Lambda/2 correction factor = 0.00150
;
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.329
_exptl_crystal_description       block
_exptl_crystal_F_000             852
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.13
_refine_diff_density_max         0.241
_refine_diff_density_min         -0.242
_refine_diff_density_rms         0.060
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.135
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     47
_refine_ls_number_reflns         554
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.134
_refine_ls_R_factor_all          0.0842
_refine_ls_R_factor_gt           0.0650
_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)+(0.0935P)²+3.5705P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1850
_refine_ls_wR_factor_ref         0.1993
_reflns_Friedel_coverage         0.000
_reflns_number_gt                407
_reflns_number_total             554
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9sc02832c2.cif
_cod_data_source_block           ADTA_7-38_dioxane-tetradecane_3-fold_publ
_cod_original_cell_volume        1986.0(7)
_cod_original_sg_symbol_H-M      'I 41/a m d'
_cod_database_code               1555264
_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   0.987
_shelx_estimated_absorpt_t_min   0.985
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups
2. Restrained distances
 O2-H2
 0.82 with sigma of 0.02
3. Others
 Fixed Sof: H3A(0.5) H3B(0.5) H1A(0.25) H1B(0.25)
4.a Secondary CH2 refined with riding coordinates:
 C3(H3A,H3B), C1(H1A,H1B)
;
_shelx_res_file
;
    pc_8_638_i41amd_200k.res created by SHELXL-2014/7

TITL pc_8_638_i41amd_200k_a.res in I4(1)/amd
REM Old TITL PC_8_638_I41amd_200K in I4(1)/amd
REM SHELXT solution in I4(1)/amd
REM R1 0.258, Rweak 0.007, Alpha 0.019, Orientation as input
REM Formula found by SHELXT: C7 O4
CELL 0.71073 16.429 16.429 7.358 90 90 90
ZERR 4 0.0026 0.0026 0.0012 0 0 0
LATT 2
SYMM 0.5-X,-Y,0.5+Z
SYMM 0.25-Y,0.75+X,0.25+Z
SYMM 0.25+Y,0.25-X,0.75+Z
SYMM 0.5-X,+Y,0.5-Z
SYMM +X,-Y,-Z
SYMM 0.25+Y,0.75+X,0.25-Z
SYMM 0.25-Y,0.25-X,0.75-Z
SFAC C H O
UNIT 80.07 115.43 32
EQIV $1 1.5-X,+Y,0.5-Z
DFIX 0.82 O2 H2

L.S. 50
PLAN  20
SIZE 0.15 0.15 0.13
TEMP -73.15
HTAB O2 O1_$1
BOND $H
list 4
fmap 2 53
acta
REM <olex2.extras>
REM <HklSrc "%.\\PC_8_638_I41amd_200K.hkl">
REM </olex2.extras>

WGHT    0.093500    3.570500
FVAR       0.43736
O1    3    0.650564    0.250000    0.224154    10.50000    0.03353    0.09506 =
         0.01803    0.00000    0.00204    0.00000
O2    3    0.719977    0.250000    0.481802    10.50000    0.02880    0.10160 =
         0.02411    0.00000    0.00087    0.00000
C4    1    0.651969    0.250000    0.389160    10.50000    0.02772    0.03679 =
         0.01803    0.00000   -0.00016    0.00000
C2    1    0.576334    0.250000    0.503796    10.50000    0.02278    0.03311 =
         0.01456    0.00000    0.00167    0.00000
C3    1    0.576113    0.326113    0.625000    10.50000    0.03041    0.03041 =
         0.01574    0.00035   -0.00035   -0.00376
AFIX  23
H3A   2    0.625578    0.326636    0.701836    10.50000   -1.20000
H3B   2    0.576634    0.375578    0.548165    10.50000   -1.20000
AFIX   0
C1    1    0.500000    0.250000    0.383449    10.25000    0.02738    0.03274 =
         0.01293    0.00000    0.00000    0.00000
AFIX  23
H1A   2    0.500000    0.298820    0.304578    10.25000   -1.20000
H1B   2    0.499999    0.201180    0.304578    10.25000   -1.20000
AFIX   0

C5    1    0.765299    0.019582    0.559946     0.75358    0.18987    0.09363 =
         0.30284   -0.00155   -0.08522   -0.00284
H2    2    0.760297    0.250000    0.412634    10.50000    0.10418
HKLF 4

REM  pc_8_638_i41amd_200k_a.res in I4(1)/amd
REM R1 =  0.0650 for     407 Fo > 4sig(Fo)  and  0.0842 for all     554 data
REM     47 parameters refined using      1 restraints

END

WGHT      0.1038      3.5757

REM Highest difference peak  0.241,  deepest hole -0.242,  1-sigma level  0.060
Q1    1   0.8494  0.0000  0.5000  10.50000  0.05    0.24
Q2    1   0.7703  0.0889  0.6223  11.00000  0.05    0.19
Q3    1   0.6106  0.2500  0.4597  10.50000  0.05    0.19
Q4    1   0.6955  0.2992  0.4300  11.00000  0.05    0.19
Q5    1   0.8479  0.1084  0.4032  11.00000  0.05    0.18
Q6    1   0.7480  0.0885  0.5076  11.00000  0.05    0.17
Q7    1   0.6678  0.1976  0.2823  11.00000  0.05    0.17
Q8    1   0.5000  0.3780  0.2980  10.50000  0.05    0.16
Q9    1   0.7692  0.0855  0.5035  11.00000  0.05    0.16
Q10   1   0.8451  0.0167  0.5762  11.00000  0.05    0.15
Q11   1   0.7298  0.2500  0.3050  10.50000  0.05    0.14
Q12   1   0.7240  0.2020  0.4091  11.00000  0.05    0.14
Q13   1   0.5467  0.2500  0.4447  10.50000  0.05    0.14
Q14   1   0.7909  0.0826  0.5033  11.00000  0.05    0.14
Q15   1   0.5000  0.2500  0.3180  10.25000  0.05    0.13
Q16   1   0.8503  0.0613  0.4986  11.00000  0.05    0.13
Q17   1   0.7869  0.2500  0.3619  10.50000  0.05    0.13
Q18   1   0.5000  0.3368  0.3963  10.50000  0.05    0.12
Q19   1   0.5943  0.2500  0.1470  10.50000  0.05    0.11
Q20   1   0.7644  0.0251  0.5156  11.00000  0.05    0.11
;
_shelx_res_checksum              58809
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-y+1/4, x+3/4, z+1/4'
'y+1/4, -x+1/4, z+3/4'
'-x+1/2, y, -z+1/2'
'x, -y, -z'
'y+1/4, x+3/4, -z+1/4'
'-y+1/4, -x+1/4, -z+3/4'
'x+1/2, y+1/2, z+1/2'
'-x+1, -y+1/2, z+1'
'-y+3/4, x+5/4, z+3/4'
'y+3/4, -x+3/4, z+5/4'
'-x+1, y+1/2, -z+1'
'x+1/2, -y+1/2, -z+1/2'
'y+3/4, x+5/4, -z+3/4'
'-y+3/4, -x+3/4, -z+5/4'
'-x, -y, -z'
'x-1/2, y, -z-1/2'
'y-1/4, -x-3/4, -z-1/4'
'-y-1/4, x-1/4, -z-3/4'
'x-1/2, -y, z-1/2'
'-x, y, z'
'-y-1/4, -x-3/4, z-1/4'
'y-1/4, x-1/4, z-3/4'
'-x+1/2, -y+1/2, -z+1/2'
'x, y+1/2, -z'
'y+1/4, -x-1/4, -z+1/4'
'-y+1/4, x+1/4, -z-1/4'
'x, -y+1/2, z'
'-x+1/2, y+1/2, z+1/2'
'-y+1/4, -x-1/4, z+1/4'
'y+1/4, x+1/4, z-1/4'
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
O1 O 0.65056(17) 0.2500 0.2242(3) 0.0489(10) Uani 1 2 d S T P
O2 O 0.71998(17) 0.2500 0.4818(4) 0.0515(10) Uani 1 2 d DS T P
C4 C 0.6520(2) 0.2500 0.3892(4) 0.0275(8) Uani 1 2 d S T P
C2 C 0.57633(19) 0.2500 0.5038(4) 0.0235(8) Uani 1 2 d S T P
C3 C 0.57611(14) 0.32611(14) 0.6250 0.0255(8) Uani 1 2 d S T P
H3A H 0.6256 0.3266 0.7018 0.031 Uiso 0.5 1 calc R . .
H3B H 0.5766 0.3756 0.5482 0.031 Uiso 0.5 1 calc R . .
C1 C 0.5000 0.2500 0.3834(6) 0.0244(11) Uani 1 4 d S T P
H1A H 0.5000 0.2988 0.3046 0.029 Uiso 0.5 2 calc RS T P
H1B H 0.5000 0.2012 0.3046 0.029 Uiso 0.5 2 calc RS T P
C5 C 0.7653(7) 0.0196(7) 0.560(3) 0.195(10) Uani 0.754(18) 1 d . . .
H2 H 0.760(3) 0.2500 0.413(8) 0.10(2) Uiso 1 2 d DS 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
O1 0.0335(15) 0.095(3) 0.0180(13) 0.000 0.0020(11) 0.000
O2 0.0288(15) 0.102(3) 0.0241(14) 0.000 0.0009(12) 0.000
C4 0.0277(18) 0.0368(19) 0.0180(15) 0.000 -0.0002(13) 0.000
C2 0.0228(17) 0.0331(17) 0.0146(14) 0.000 0.0017(13) 0.000
C3 0.0304(12) 0.0304(12) 0.0157(14) 0.0004(9) -0.0004(9) -0.0038(14)
C1 0.027(2) 0.033(3) 0.0129(19) 0.000 0.000 0.000
C5 0.190(14) 0.094(11) 0.30(3) -0.002(9) -0.085(16) -0.003(7)
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
C4 O2 H2 111(5) . .
O1 C4 O2 122.5(3) . .
O1 C4 C2 123.1(3) . .
O2 C4 C2 114.4(3) . .
C4 C2 C3 109.15(18) . 27_566
C4 C2 C3 109.15(18) . .
C4 C2 C1 110.6(3) . .
C3 C2 C3 109.0(2) . 27_566
C1 C2 C3 109.45(16) . 27_566
C1 C2 C3 109.45(16) . .
C2 C3 C2 109.9(3) 20_657 .
C2 C3 H3A 109.7 . .
C2 C3 H3A 109.7 20_657 .
C2 C3 H3B 109.7 . .
C2 C3 H3B 109.7 20_657 .
H3A C3 H3B 108.2 . .
C2 C1 C2 109.5(4) 10_554 .
C2 C1 H1A 109.8 . .
C2 C1 H1A 109.8 10_554 .
C2 C1 H1B 109.8 10_554 .
C2 C1 H1B 109.8 . .
H1A C1 H1B 108.2 . .
C5 C5 C5 110.3(17) 6_556 16
C5 C5 C5 125.2(17) 16 11_534
C5 C5 C5 37.6(15) 6_556 11_534
C5 C5 C5 127(2) 6_556 12_554
C5 C5 C5 155.5(7) 12_554 11_534
C5 C5 C5 32.1(12) 16 12_554
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 C4 1.214(4) .
O2 C4 1.309(4) .
O2 H2 0.84(2) .
C4 C2 1.502(4) .
C2 C3 1.536(3) 27_566
C2 C3 1.536(3) .
C2 C1 1.535(4) .
C3 C2 1.536(3) 20_657
C3 H3A 0.9900 .
C3 H3B 0.9900 .
C1 C2 1.535(4) 10_554
C1 H1A 0.9900 .
C1 H1B 0.9900 .
C5 C5 1.09(3) 6_556
C5 C5 1.928(6) 12_554
C5 C5 1.928(6) 11_534
C5 C5 1.25(4) 16
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
_geom_hbond_site_symmetry_A
O2 H2 O1 0.84(2) 1.78(2) 2.612(4) 177(8) 5_655
