#------------------------------------------------------------------------------
#$Date: 2019-11-24 14:53:59 +0100 (Sun 24 de Nov de 2019) $
#$Revision: 238432 $
#$URL: svn://www.crystallography.net/cod/cif/1/55/52/1555266.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_1555266
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         'C9 H6 O6'
_chemical_formula_sum            'C9 H6 O6'
_chemical_formula_weight         210.14
_space_group_crystal_system      monoclinic
_space_group_IT_number           12
_space_group_name_Hall           '-C 2y'
_space_group_name_H-M_alt        'C 1 2/m 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2018-05-21
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.18 svn.r3508 for OlexSys, GUI svn.r5497)
;
_audit_update_record
;
2019-05-10 deposited with the CCDC.	2019-08-20 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 95.076(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   26.075(2)
_cell_length_b                   16.4837(12)
_cell_length_c                   3.6749(3)
_cell_measurement_reflns_used    3425
_cell_measurement_temperature    200
_cell_measurement_theta_max      26.318
_cell_measurement_theta_min      2.471
_cell_volume                     1573.3(2)
_computing_cell_refinement       'SAINT v7.68A (Bruker, 2009)'
_computing_data_collection
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_data_reduction        'SAINT v7.68A (Bruker, 2009)'
_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 0.998
_diffrn_measured_fraction_theta_max 0.994
_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  0.0430
_diffrn_reflns_av_unetI/netI     0.0357
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       31
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       3
_diffrn_reflns_limit_l_min       -4
_diffrn_reflns_number            8938
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.686
_diffrn_reflns_theta_min         2.471
_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    0.077
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.4499
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.0920 before and 0.0644 after correction. The Ratio of minimum to maximum transmission is 0.6036. The λ/2 correction factor is 0.0015.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    0.887
_exptl_crystal_description       hexagonal
_exptl_crystal_F_000             432
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.14
_exptl_crystal_size_min          0.09
_refine_diff_density_max         0.209
_refine_diff_density_min         -0.230
_refine_diff_density_rms         0.034
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.042
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     75
_refine_ls_number_reflns         1723
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.042
_refine_ls_R_factor_all          0.0547
_refine_ls_R_factor_gt           0.0406
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0633P)²+0.2903P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1101
_refine_ls_wR_factor_ref         0.1206
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1324
_reflns_number_total             1723
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9sc02832c2.cif
_cod_data_source_block           TMA_2-33_Pentane_Activated_C2c_200K_publ
_cod_database_code               1555266
_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   0.993
_shelx_estimated_absorpt_t_min   0.989
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All O(H) groups
2. Others
 Fixed Sof: H1(0.5)
3.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C5(H5)
3.b Idealised tetrahedral OH refined as rotating group:
 O1(H1), O2(H2)
;
_shelx_res_file
;
    pc_ht_1_i233_pentane_200k.res created by SHELXL-2014/7

TITL pc_ht_1_i233_pentane_200k_a.res in C2/m
REM Old TITL PC_HT_1_i233_pentane_200K in C2/m #12
REM SHELXT solution in C2/m
REM R1 0.169, Rweak 0.005, Alpha 0.043, Orientation as input
REM Formula found by SHELXT: C9 O6
CELL 0.71073 26.0746 16.4837 3.6749 90 95.076 90
ZERR 4 0.002 0.0012 0.0003 0 0.002 0
LATT 7
SYMM -X,+Y,-Z
SFAC C H O
UNIT 36 24 24
EQIV $1 0.5-X,0.5-Y,-Z
EQIV $2 1-X,+Y,2-Z

L.S. 20
PLAN  20
SIZE 0.09 0.14 0.15
TEMP -73.15
HTAB O2 O3_$1
HTAB O1 O1_$2
BOND $H
list 4
fmap 2 53
acta
OMIT 2 0 0
OMIT 1 1 0
REM <olex2.extras>
REM <HklSrc "%.\\PC_HT_1_i233_pentane_200K.hkl">
REM </olex2.extras>

WGHT    0.063300    0.290300
FVAR       0.77772
O1    3    0.454080    0.567713    0.819642    11.00000    0.03943    0.05158 =
         0.07077   -0.00063   -0.02080   -0.00687
AFIX 147
H1    2    0.484775    0.560625    0.903532    10.50000   -1.50000
AFIX   0
O2    3    0.304888    0.284317    0.267291    11.00000    0.05363    0.03410 =
         0.06794   -0.00033   -0.02004   -0.00081
AFIX 147
H2    2    0.288152    0.243891    0.183450    11.00000   -1.50000
AFIX   0
O3    3    0.240202    0.350974   -0.040623    11.00000    0.04418    0.04315 =
         0.05891   -0.00133   -0.01982   -0.00524
C1    1    0.433581    0.500000    0.738966    10.50000    0.03198    0.03833 =
         0.03493    0.00000   -0.00392    0.00000
C2    1    0.381208    0.500000    0.539927    10.50000    0.02980    0.03970 =
         0.03045    0.00000   -0.00414    0.00000
C3    1    0.356889    0.426581    0.448623    11.00000    0.03372    0.03579 =
         0.03317    0.00106   -0.00404    0.00258
AFIX  43
H3    2    0.373592    0.376668    0.511717    11.00000   -1.20000
AFIX   0
C4    1    0.307861    0.427016    0.263983    11.00000    0.03382    0.03583 =
         0.03148   -0.00066   -0.00382   -0.00112
C5    1    0.283300    0.500000    0.172457    10.50000    0.02978    0.03898 =
         0.03236    0.00000   -0.00579    0.00000
AFIX  43
H5    2    0.249800    0.500000    0.047629    10.50000   -1.20000
AFIX   0
C6    1    0.281989    0.349182    0.155055    11.00000    0.03545    0.03535 =
         0.03920   -0.00009   -0.00690   -0.00001
HKLF 4

REM  pc_ht_1_i233_pentane_200k_a.res in C2/m
REM R1 =  0.0406 for    1324 Fo > 4sig(Fo)  and  0.0547 for all    1723 data
REM     75 parameters refined using      0 restraints

END

WGHT      0.0633      0.2903

REM Highest difference peak  0.209,  deepest hole -0.230,  1-sigma level  0.034
Q1    1   0.2989  0.3947  0.2079  11.00000  0.05    0.21
Q2    1   0.3991  0.5000  0.6060  10.50000  0.05    0.19
Q3    1   0.3212  0.4240  0.4076  11.00000  0.05    0.14
Q4    1   0.2247  0.3098 -0.1268  11.00000  0.05    0.14
Q5    1   0.2998  0.4595  0.1773  11.00000  0.05    0.12
Q6    1   0.3634  0.4603  0.5248  11.00000  0.05    0.12
Q7    1   0.3327  0.4274  0.2816  11.00000  0.05    0.12
Q8    1   0.4798  0.5796  0.9272  11.00000  0.05    0.12
Q9    1   0.3738  0.4672  0.4498  11.00000  0.05    0.11
Q10   1   0.4627  0.5404  0.6689  11.00000  0.05    0.10
Q11   1   0.3647  0.2597  0.4605  11.00000  0.05    0.09
Q12   1   0.4635  0.7458  0.8363  11.00000  0.05    0.09
Q13   1   0.3980  0.3356  0.5704  11.00000  0.05    0.08
Q14   1   0.4541  0.6724  0.8120  11.00000  0.05    0.08
Q15   1   0.4436  0.6594  0.7782  11.00000  0.05    0.08
Q16   1   0.3206  0.2583  0.5870  11.00000  0.05    0.08
Q17   1   0.2403  0.5000  0.1675  10.50000  0.05    0.08
Q18   1   0.1853  0.4180 -0.2345  11.00000  0.05    0.08
Q19   1   0.2789  0.4598  0.5449  11.00000  0.05    0.07
Q20   1   0.2346  0.4012  0.3600  11.00000  0.05    0.07
;
_shelx_res_checksum              98835
_olex2_submission_special_instructions 'No special instructions were received'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'
'-x, -y, -z'
'x, -y, z'
'-x+1/2, -y+1/2, -z'
'x+1/2, -y+1/2, z'
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 0.45408(4) 0.56771(6) 0.8196(3) 0.0555(3) Uani 1 1 d . . .
H1 H 0.4848 0.5606 0.9035 0.083 Uiso 0.5 1 calc GR . .
O2 O 0.30489(4) 0.28432(5) 0.2673(3) 0.0534(3) Uani 1 1 d . . .
H2 H 0.2882 0.2439 0.1835 0.080 Uiso 1 1 calc GR . .
O3 O 0.24020(3) 0.35097(6) -0.0406(3) 0.0502(3) Uani 1 1 d . . .
C1 C 0.43358(6) 0.5000 0.7390(5) 0.0355(4) Uani 1 2 d S T P
C2 C 0.38121(6) 0.5000 0.5399(4) 0.0337(4) Uani 1 2 d S T P
C3 C 0.35689(5) 0.42658(7) 0.4486(3) 0.0346(3) Uani 1 1 d . . .
H3 H 0.3736 0.3767 0.5117 0.042 Uiso 1 1 calc R . .
C4 C 0.30786(4) 0.42702(7) 0.2640(3) 0.0341(3) Uani 1 1 d . . .
C5 C 0.28330(6) 0.5000 0.1725(4) 0.0342(4) Uani 1 2 d S T P
H5 H 0.2498 0.5000 0.0476 0.041 Uiso 1 2 calc RS T P
C6 C 0.28199(5) 0.34918(7) 0.1551(3) 0.0373(3) Uani 1 1 d . . .
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 0.0394(5) 0.0516(6) 0.0708(7) -0.0006(5) -0.0208(5) -0.0069(4)
O2 0.0536(6) 0.0341(5) 0.0679(7) -0.0003(4) -0.0200(5) -0.0008(4)
O3 0.0442(5) 0.0431(5) 0.0589(6) -0.0013(4) -0.0198(4) -0.0052(4)
C1 0.0320(8) 0.0383(9) 0.0349(8) 0.000 -0.0039(7) 0.000
C2 0.0298(8) 0.0397(8) 0.0305(8) 0.000 -0.0041(6) 0.000
C3 0.0337(6) 0.0358(6) 0.0332(6) 0.0011(5) -0.0040(5) 0.0026(4)
C4 0.0338(6) 0.0358(6) 0.0315(6) -0.0007(5) -0.0038(5) -0.0011(4)
C5 0.0298(8) 0.0390(8) 0.0324(8) 0.000 -0.0058(6) 0.000
C6 0.0354(6) 0.0353(6) 0.0392(6) -0.0001(5) -0.0069(5) 0.0000(5)
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
C1 O1 H1 109.5 . .
C6 O2 H2 109.5 . .
O1 C1 O1 124.45(15) . 6_565
O1 C1 C2 117.77(8) . .
O1 C1 C2 117.77(8) 6_565 .
C3 C2 C1 119.72(7) 6_565 .
C3 C2 C1 119.71(7) . .
C3 C2 C3 120.57(15) 6_565 .
C2 C3 H3 120.3 . .
C4 C3 C2 119.42(11) . .
C4 C3 H3 120.3 . .
C3 C4 C6 120.08(10) . .
C5 C4 C3 120.36(11) . .
C5 C4 C6 119.54(11) . .
C4 C5 C4 119.86(15) . 6_565
C4 C5 H5 120.1 6_565 .
C4 C5 H5 120.1 . .
O2 C6 C4 116.60(10) . .
O3 C6 O2 124.37(11) . .
O3 C6 C4 119.02(10) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 H1 0.8400 .
O1 C1 1.2615(12) .
O2 H2 0.8400 .
O2 C6 1.2753(14) .
O3 C6 1.2516(15) .
C1 O1 1.2615(12) 6_565
C1 C2 1.491(2) .
C2 C3 1.3934(14) .
C2 C3 1.3934(14) 6_565
C3 H3 0.9500 .
C3 C4 1.3933(16) .
C4 C5 1.3901(14) .
C4 C6 1.4878(16) .
C5 C4 1.3902(14) 6_565
C5 H5 0.9500 .
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
O1 H1 O1 0.84 1.82 2.6325(17) 163.1 2_657
O2 H2 O3 0.84 1.79 2.6222(13) 171.5 7
