#------------------------------------------------------------------------------
#$Date: 2019-11-24 15:53:59 +0200 (Sun, 24 Nov 2019) $
#$Revision: 238432 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/55/52/1555271.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_1555271
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, 5.38(H2 O)'
_chemical_formula_sum            'C9 H16.75 O11.38'
_chemical_formula_weight         306.97
_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             2018-07-02
_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                 93.333(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   25.768(4)
_cell_length_b                   16.425(2)
_cell_length_c                   3.6006(5)
_cell_measurement_reflns_used    3371
_cell_measurement_temperature    100
_cell_measurement_theta_max      26.450
_cell_measurement_theta_min      2.480
_cell_volume                     1521.3(4)
_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    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      100
_diffrn_detector                 CCD
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku Saturn724+'
_diffrn_measured_fraction_theta_full 0.994
_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  0.0521
_diffrn_reflns_av_unetI/netI     0.0433
_diffrn_reflns_Laue_measured_fraction_full 0.994
_diffrn_reflns_Laue_measured_fraction_max 0.994
_diffrn_reflns_limit_h_max       27
_diffrn_reflns_limit_h_min       -32
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       4
_diffrn_reflns_limit_l_min       -4
_diffrn_reflns_number            8267
_diffrn_reflns_point_group_measured_fraction_full 0.994
_diffrn_reflns_point_group_measured_fraction_max 0.994
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.371
_diffrn_reflns_theta_min         2.480
_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    0.127
_exptl_absorpt_correction_T_max  0.7454
_exptl_absorpt_correction_T_min  0.4482
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
'SADABS-2008/1 (Bruker,2008) was used for absorption correction. wR2(int) was 0.1020 before and 0.0711 after correction. The Ratio of minimum to maximum transmission is 0.6013. The λ/2 correction factor is 0.0015.'
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.340
_exptl_crystal_description       block
_exptl_crystal_F_000             647
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.11
_exptl_crystal_size_min          0.1
_refine_diff_density_max         0.588
_refine_diff_density_min         -0.433
_refine_diff_density_rms         0.118
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.785
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     115
_refine_ls_number_reflns         1618
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.785
_refine_ls_R_factor_all          0.1014
_refine_ls_R_factor_gt           0.0887
_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)+(0.1000P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2374
_refine_ls_wR_factor_ref         0.2458
_reflns_Friedel_coverage         0.000
_reflns_number_gt                1293
_reflns_number_total             1618
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            c9sc02832c2.cif
_cod_data_source_block           TMA_8-35_butanol-1-3-dimethoxybenzene_publ
_cod_database_code               1555271
_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   0.974
_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) O1W(0.25) O2W(0.25) O3W(0.25) O4W(0.25) O5W(0.5) O6W(0.25)
 O7W(0.5) O8W(0.25) O9W(0.125) O10W(0.0625)
3.a Aromatic/amide H refined with riding coordinates:
 C3(H3), C6(H6)
3.b Idealised tetrahedral OH refined as rotating group:
 O1(H1), O2(H2)
;
_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
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.45458(7) 0.56825(12) 0.8180(6) 0.0373(6) Uani 1 1 d . . . . .
H1 H 0.4855 0.5613 0.8999 0.056 Uiso 0.5 1 calc GR . . . .
O2 O 0.30514(7) 0.71676(11) 0.2787(5) 0.0335(6) Uani 1 1 d . . . . .
H2 H 0.2902 0.7575 0.1808 0.050 Uiso 1 1 calc GR . . . .
O3 O 0.23999(6) 0.65025(11) -0.0300(5) 0.0311(6) Uani 1 1 d . . . . .
C1 C 0.43416(12) 0.5000 0.7382(9) 0.0236(8) Uani 1 2 d S T P . .
C2 C 0.38133(12) 0.5000 0.5434(9) 0.0238(8) Uani 1 2 d S T P . .
C3 C 0.35683(10) 0.57359(15) 0.4546(7) 0.0246(6) Uani 1 1 d . . . . .
H3 H 0.3737 0.6237 0.5155 0.030 Uiso 1 1 calc R . . . .
C4 C 0.30752(9) 0.57324(14) 0.2761(7) 0.0227(6) Uani 1 1 d . . . . .
C5 C 0.28131(9) 0.65110(15) 0.1646(7) 0.0244(6) Uani 1 1 d . . . . .
C6 C 0.28262(13) 0.5000 0.1860(9) 0.0227(7) Uani 1 2 d S T P . .
H6 H 0.2489 0.5000 0.0639 0.027 Uiso 1 2 calc RS T P . .
O1W O 0.1500(12) 0.5000 0.498(9) 0.289(19) Uani 0.5 2 d S T P A 1
O2W O 0.1465(6) 0.5000 0.056(10) 0.225(11) Uani 0.5 2 d S T P B 2
O3W O 0.1182(19) 0.581(3) -0.014(12) 0.233(15) Uiso 0.25 1 d . . . C 3
O4W O 0.489(2) 0.763(4) 1.249(13) 0.30(2) Uiso 0.25 1 d . . . D 4
O5W O 0.4202(13) 0.783(2) 0.809(13) 0.307(15) Uiso 0.5 1 d . . . E 5
O6W O 0.4270(12) 0.774(2) 1.059(14) 0.171(10) Uiso 0.25 1 d . . . F 6
O7W O 0.4300(7) 0.7760(12) 0.419(8) 0.212(6) Uiso 0.5 1 d . . . G 7
O8W O 0.3949(16) 0.877(2) 0.581(11) 0.217(13) Uiso 0.25 1 d . . . H 8
O9W O 0.4963(17) 1.0000 0.345(9) 0.178(15) Uiso 0.25 2 d S T P I 9
O10W O 0.5000 1.0000 0.0000 0.22(3) Uiso 0.25 4 d S T P J 10
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 . .
C5 O2 H2 109.5 . .
O1 C1 O1 124.9(3) . 6_565
O1 C1 C2 117.53(16) . .
O1 C1 C2 117.54(16) 6_565 .
C3 C2 C1 119.75(15) . .
C3 C2 C1 119.76(15) 6_565 .
C3 C2 C3 120.5(3) . 6_565
C2 C3 H3 120.2 . .
C4 C3 C2 119.5(2) . .
C4 C3 H3 120.2 . .
C3 C4 C5 120.6(2) . .
C3 C4 C6 120.5(2) . .
C6 C4 C5 118.9(2) . .
O2 C5 C4 115.5(2) . .
O3 C5 O2 124.3(2) . .
O3 C5 C4 120.2(2) . .
C4 C6 C4 119.5(3) . 6_565
C4 C6 H6 120.3 6_565 .
C4 C6 H6 120.3 . .
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 1.264(2) .
O2 H2 0.8400 .
O2 C5 1.296(3) .
O3 C5 1.240(3) .
C1 O1 1.264(2) 6_565
C1 C2 1.495(4) .
C2 C3 1.392(3) 6_565
C2 C3 1.392(3) .
C3 H3 0.9500 .
C3 C4 1.390(4) .
C4 C5 1.490(3) .
C4 C6 1.393(3) .
C6 C4 1.393(3) 6_565
C6 H6 0.9500 .
O9W O9W 1.12(7) 5_676
