#------------------------------------------------------------------------------
#$Date: 2019-11-24 15:53:59 +0200 (Sun, 24 Nov 2019) $
#$Revision: 238432 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/52/1555267.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_1555267
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
_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                 96.283(6)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   26.240(5)
_cell_length_b                   16.529(3)
_cell_length_c                   3.7452(7)
_cell_measurement_reflns_used    3253
_cell_measurement_temperature    350
_cell_measurement_theta_max      25.796
_cell_measurement_theta_min      2.465
_cell_volume                     1614.6(5)
_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)'
_diffrn_ambient_temperature      350
_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 0.997
_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  0.0379
_diffrn_reflns_av_unetI/netI     0.0327
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_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            9783
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.472
_diffrn_reflns_theta_min         2.464
_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
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.4607
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.0824 before and 0.0597 after correction. The Ratio of minimum to maximum transmission is 0.6181. The λ/2 correction factor is 0.0015.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    0.864
_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         0.148
_refine_diff_density_min         -0.158
_refine_diff_density_rms         0.026
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.020
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     75
_refine_ls_number_reflns         1731
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.020
_refine_ls_R_factor_all          0.0622
_refine_ls_R_factor_gt           0.0423
_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)+(0.0654P)²+0.2603P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1190
_refine_ls_wR_factor_ref         0.1342
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1183
_reflns_number_total             1731
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9sc02832c2.cif
_cod_data_source_block           TMA_2-33_Pentane_Activated_C2c_350K_publ
_cod_database_code               1555267
_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_activated.res created by SHELXL-2014/7

TITL PC_HT_1_i233_pentane_activated.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 26.24 16.5291 3.7452 90 96.283 90
ZERR 8 0.0053 0.0033 0.0007 0 0.006 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 76.85
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_activated.hkl">
REM </olex2.extras>

WGHT    0.065400    0.260300
FVAR       0.81303
O1    3    0.453757    0.567137    0.820539    11.00000    0.06382    0.07869 =
         0.12802   -0.00112   -0.03729   -0.00839
AFIX 147
H1    2    0.483663    0.560018    0.903233    10.50000   -1.50000
AFIX   0
O2    3    0.304750    0.285166    0.258195    11.00000    0.08823    0.05637 =
         0.13150   -0.00112   -0.04158   -0.00191
AFIX 147
H2    2    0.289315    0.246241    0.163468    11.00000   -1.50000
AFIX   0
O3    3    0.239856    0.351584   -0.038540    11.00000    0.07458    0.06776 =
         0.11746   -0.00177   -0.04054   -0.00799
C1    1    0.433166    0.500000    0.738716    10.50000    0.05180    0.06113 =
         0.07003    0.00000   -0.01203    0.00000
C2    1    0.380972    0.500000    0.538747    10.50000    0.04825    0.06138 =
         0.05916    0.00000   -0.00942    0.00000
C3    1    0.356743    0.427024    0.446782    11.00000    0.05444    0.05811 =
         0.06443    0.00087   -0.01024    0.00381
AFIX  43
H3    2    0.373122    0.378334    0.509070    11.00000   -1.20000
AFIX   0
C4    1    0.307779    0.427187    0.260756    11.00000    0.05439    0.05774 =
         0.06133   -0.00110   -0.01010   -0.00253
C5    1    0.283442    0.500000    0.168647    10.50000    0.04947    0.06335 =
         0.06208    0.00000   -0.01284    0.00000
AFIX  43
H5    2    0.250725    0.499999    0.044820    10.50000   -1.20000
AFIX   0
C6    1    0.282108    0.349573    0.152722    11.00000    0.05949    0.05666 =
         0.07714   -0.00082   -0.01701   -0.00056
HKLF 4

REM  PC_HT_1_i233_pentane_activated.res in C2/m
REM R1 =  0.0423 for    1183 Fo > 4sig(Fo)  and  0.0622 for all    1731 data
REM     75 parameters refined using      0 restraints

END

WGHT      0.0666      0.2507

REM Highest difference peak  0.148,  deepest hole -0.158,  1-sigma level  0.026
Q1    1   0.2224  0.3081 -0.1193  11.00000  0.05    0.15
Q2    1   0.2982  0.3999  0.2112  11.00000  0.05    0.14
Q3    1   0.3937  0.5000  0.6157  10.50000  0.05    0.13
Q4    1   0.4643  0.5406  0.6445  11.00000  0.05    0.12
Q5    1   0.4821  0.5770  0.9402  11.00000  0.05    0.12
Q6    1   0.3015  0.4557  0.2095  11.00000  0.05    0.10
Q7    1   0.3799  0.3563  0.5524  11.00000  0.05    0.09
Q8    1   0.4398  0.6568  0.7394  11.00000  0.05    0.09
Q9    1   0.3787  0.5190  0.4574  11.00000  0.05    0.08
Q10   1   0.2255  0.3528  0.1898  11.00000  0.05    0.08
Q11   1   0.2474  0.5000 -0.0716  10.50000  0.05    0.07
Q12   1   0.4499  0.5571  0.8747  11.00000  0.05    0.06
Q13   1   0.4574  0.6688  0.8338  11.00000  0.05    0.06
Q14   1   0.2081  0.4202 -0.1584  11.00000  0.05    0.06
Q15   1   0.3485  0.5000  0.7476  10.50000  0.05    0.06
Q16   1   0.2124  0.4297 -0.1282  11.00000  0.05    0.06
Q17   1   0.2280  0.5000  0.1964  10.50000  0.05    0.06
Q18   1   0.4430  0.5400  0.9939  11.00000  0.05    0.06
Q19   1   0.3567  0.5000  0.8557  10.50000  0.05    0.05
Q20   1   0.3571  0.2750  0.4645  11.00000  0.05    0.05
;
_shelx_res_checksum              38008
_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 0.45376(4) 0.56714(6) 0.8205(4) 0.0937(5) Uani 1 1 d . . .
H1 H 0.4837 0.5600 0.9032 0.141 Uiso 0.5 1 calc GR . .
O2 O 0.30475(4) 0.28517(6) 0.2582(4) 0.0960(4) Uani 1 1 d . . .
H2 H 0.2893 0.2462 0.1635 0.144 Uiso 1 1 calc GR . .
O3 O 0.23986(4) 0.35158(7) -0.0385(3) 0.0904(4) Uani 1 1 d . . .
C1 C 0.43317(7) 0.5000 0.7387(5) 0.0624(5) Uani 1 2 d S T P
C2 C 0.38097(7) 0.5000 0.5387(5) 0.0574(5) Uani 1 2 d S T P
C3 C 0.35674(5) 0.42702(8) 0.4468(4) 0.0602(4) Uani 1 1 d . . .
H3 H 0.3731 0.3783 0.5091 0.072 Uiso 1 1 calc R . .
C4 C 0.30778(5) 0.42719(8) 0.2608(4) 0.0590(4) Uani 1 1 d . . .
C5 C 0.28344(7) 0.5000 0.1686(5) 0.0597(5) Uani 1 2 d S T P
H5 H 0.2507 0.5000 0.0448 0.072 Uiso 1 2 calc RS T P
C6 C 0.28211(5) 0.34957(8) 0.1527(4) 0.0662(4) 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 0.0638(7) 0.0787(8) 0.1280(11) -0.0011(6) -0.0373(7) -0.0084(5)
O2 0.0882(8) 0.0564(6) 0.1315(10) -0.0011(6) -0.0416(7) -0.0019(5)
O3 0.0746(7) 0.0678(7) 0.1175(9) -0.0018(6) -0.0405(6) -0.0080(5)
C1 0.0518(10) 0.0611(11) 0.0700(12) 0.000 -0.0120(9) 0.000
C2 0.0482(9) 0.0614(10) 0.0592(10) 0.000 -0.0094(8) 0.000
C3 0.0544(7) 0.0581(7) 0.0644(8) 0.0009(6) -0.0102(6) 0.0038(6)
C4 0.0544(7) 0.0577(8) 0.0613(8) -0.0011(6) -0.0101(6) -0.0025(6)
C5 0.0495(9) 0.0633(11) 0.0621(11) 0.000 -0.0128(8) 0.000
C6 0.0595(8) 0.0567(8) 0.0771(9) -0.0008(7) -0.0170(7) -0.0006(6)
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 123.91(17) . 6_565
O1 C1 C2 118.04(9) 6_565 .
O1 C1 C2 118.04(9) . .
C3 C2 C1 119.74(8) . .
C3 C2 C1 119.74(8) 6_565 .
C3 C2 C3 120.52(16) 6_565 .
C2 C3 H3 120.2 . .
C2 C3 C4 119.63(13) . .
C4 C3 H3 120.2 . .
C3 C4 C6 120.06(12) . .
C5 C4 C3 120.00(13) . .
C5 C4 C6 119.92(12) . .
C4 C5 C4 120.22(16) . 6_565
C4 C5 H5 119.9 . .
C4 C5 H5 119.9 6_565 .
O2 C6 C4 117.38(12) . .
O3 C6 O2 123.95(13) . .
O3 C6 C4 118.66(11) . .
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
O1 H1 0.8200 .
O1 C1 1.2574(13) .
O2 H2 0.8200 .
O2 C6 1.2613(16) .
O3 C6 1.2528(16) .
C1 O1 1.2574(13) 6_565
C1 C2 1.487(2) .
C2 C3 1.3892(16) .
C2 C3 1.3892(16) 6_565
C3 H3 0.9300 .
C3 C4 1.3929(18) .
C4 C5 1.3882(15) .
C4 C6 1.4845(18) .
C5 C4 1.3882(16) 6_565
C5 H5 0.9300 .
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 0.82 1.85 2.642(2) 163.4 2_657
O2 H2 O3 0.82 1.83 2.6354(15) 168.0 7
