# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2016

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_15jnac842
_database_code_depnum_ccdc_archive 'CCDC 1056172'
_audit_update_record             
;
2015-03-25 deposited with the CCDC.
2016-02-23 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2013
_chemical_name_systematic        
;
 ?
;
_chemical_name_common            5-hydroxy-2-hydroxymethylpyridin-4(1H)-one
_chemical_melting_point          ?
_chemical_formula_moiety         'C6 H7 N O3'
_chemical_formula_sum            'C6 H7 N O3'
_chemical_formula_weight         141.13

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'
N N 0.0061 0.0033 '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'

_space_group_crystal_system      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'

_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.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'x+1/2, -y+1/2, -z'
'-x, y+1/2, -z+1/2'

_cell_length_a                   6.8410(4)
_cell_length_b                   7.0291(3)
_cell_length_c                   12.6402(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     607.82(5)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    3530
_cell_measurement_theta_min      3.317
_cell_measurement_theta_max      27.480

_exptl_crystal_description       block
_exptl_crystal_colour            yellow
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.542
_exptl_crystal_F_000             296
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.100
_exptl_crystal_size_mid          0.100
_exptl_crystal_size_min          0.100
_exptl_absorpt_coefficient_mu    0.125
_shelx_estimated_absorpt_T_min   0.988
_shelx_estimated_absorpt_T_max   0.988
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.6959
_exptl_absorpt_correction_T_max  0.7456
_exptl_absorpt_process_details   SADABS

_exptl_special_details           
;
 ?
;

_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'high brilliance microfocus sealed tube'
_diffrn_measurement_device_type  'Bruker D8 Venture'
_diffrn_measurement_method       'ω and φ scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            8040
_diffrn_reflns_av_unetI/netI     0.0167
_diffrn_reflns_av_R_equivalents  0.0245
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_l_min       -14
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         3.223
_diffrn_reflns_theta_max         27.492
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_point_group_measured_fraction_full 0.999
_reflns_number_total             1390
_reflns_number_gt                1346
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.667
_reflns_Friedel_fraction_max     0.998
_reflns_Friedel_fraction_full    1.000

_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'Bruker Apex2, 2014'
_computing_cell_refinement       'Bruker Apex2, 2014'
_computing_data_reduction        'SAINT v8.34A (Bruker, 2013)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2013 (Sheldrick, 2013)'
_computing_molecular_graphics    'PLATON (Spek, 2009)'
_computing_publication_material  'SHELXL-2013 (Sheldrick, 2013)'

_refine_special_details          
;
 Flack x determined using 532 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0324P)²+0.1750P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    constr
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 532 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons and Flack (2004), Acta Cryst. A60, s61).
;
_refine_ls_abs_structure_Flack   -0.5(4)
_chemical_absolute_configuration ?
_refine_ls_number_reflns         1390
_refine_ls_number_parameters     91
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0278
_refine_ls_R_factor_gt           0.0264
_refine_ls_wR_factor_ref         0.0675
_refine_ls_wR_factor_gt          0.0666
_refine_ls_goodness_of_fit_ref   1.094
_refine_ls_restrained_S_all      1.094
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000

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
O4 O 0.23189(17) 0.34259(16) 0.09052(9) 0.0142(3) Uani 1 1 d . . . . .
O5 O -0.06312(17) 0.53334(19) 0.19844(9) 0.0171(3) Uani 1 1 d . . . . .
H5A H -0.0597 0.5024 0.1343 0.026 Uiso 1 1 d R U . . .
O8 O 0.67093(16) 0.50631(16) 0.49192(8) 0.0141(3) Uani 1 1 d . . . . .
H8A H 0.6997 0.6113 0.4642 0.021 Uiso 1 1 d R U . . .
N1 N 0.30973(18) 0.49731(19) 0.39740(10) 0.0117(3) Uani 1 1 d . . . . .
H1A H 0.3237 0.5274 0.4646 0.014 Uiso 1 1 d R U . . .
C2 C 0.4580(2) 0.4100(2) 0.34687(13) 0.0120(3) Uani 1 1 d . . . . .
C3 C 0.4383(2) 0.3610(2) 0.24236(13) 0.0124(3) Uani 1 1 d . . . . .
H3 H 0.5453 0.3043 0.2064 0.015 Uiso 1 1 d R U . . .
C4 C 0.2614(2) 0.3936(2) 0.18714(12) 0.0119(3) Uani 1 1 d . . . . .
C5 C 0.1104(2) 0.4909(2) 0.24449(12) 0.0125(3) Uani 1 1 d . . . . .
C6 C 0.1388(2) 0.5405(2) 0.34759(12) 0.0130(3) Uani 1 1 d . . . . .
H6 H 0.0386 0.6057 0.3850 0.016 Uiso 1 1 d R U . . .
C7 C 0.6392(2) 0.3691(2) 0.41126(13) 0.0140(3) Uani 1 1 d . . . . .
H7A H 0.6268 0.2418 0.4440 0.017 Uiso 1 1 d R U . . .
H7B H 0.7540 0.3667 0.3636 0.017 Uiso 1 1 d R U . . .

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
O4 0.0183(6) 0.0145(5) 0.0097(5) -0.0009(4) -0.0003(5) 0.0019(5)
O5 0.0136(5) 0.0245(6) 0.0133(5) -0.0050(5) -0.0028(4) 0.0053(5)
O8 0.0164(5) 0.0151(6) 0.0109(5) 0.0001(5) -0.0002(4) -0.0028(5)
N1 0.0129(6) 0.0127(6) 0.0096(6) -0.0002(5) 0.0003(5) -0.0010(6)
C2 0.0122(7) 0.0101(7) 0.0136(7) 0.0016(6) 0.0005(6) -0.0002(6)
C3 0.0126(7) 0.0109(7) 0.0139(7) -0.0008(6) 0.0029(6) 0.0006(6)
C4 0.0152(8) 0.0090(7) 0.0114(7) 0.0018(6) 0.0018(6) -0.0007(6)
C5 0.0120(7) 0.0118(8) 0.0138(7) 0.0009(6) 0.0004(5) -0.0001(6)
C6 0.0111(7) 0.0135(7) 0.0142(7) -0.0010(6) 0.0021(6) 0.0007(6)
C7 0.0143(7) 0.0137(7) 0.0141(7) -0.0013(6) -0.0022(7) 0.0022(6)

_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O4 C4 1.2887(19) . ?
O5 C5 1.3555(19) . ?
O5 H5A 0.8400 . ?
O8 C7 1.4200(19) . ?
O8 H8A 0.8400 . ?
N1 C2 1.347(2) . ?
N1 C6 1.363(2) . ?
N1 H1A 0.8801 . ?
C2 C3 1.372(2) . ?
C2 C7 1.510(2) . ?
C3 C4 1.416(2) . ?
C3 H3 0.9500 . ?
C4 C5 1.435(2) . ?
C5 C6 1.363(2) . ?
C6 H6 0.9500 . ?
C7 H7A 0.9900 . ?
C7 H7B 0.9900 . ?

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
_geom_angle_publ_flag
C5 O5 H5A 109.5 . . ?
C7 O8 H8A 109.5 . . ?
C2 N1 C6 121.93(14) . . ?
C2 N1 H1A 119.0 . . ?
C6 N1 H1A 119.0 . . ?
N1 C2 C3 119.81(15) . . ?
N1 C2 C7 116.69(14) . . ?
C3 C2 C7 123.50(15) . . ?
C2 C3 C4 121.22(15) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?
O4 C4 C3 123.79(15) . . ?
O4 C4 C5 119.91(15) . . ?
C3 C4 C5 116.29(14) . . ?
O5 C5 C6 118.62(14) . . ?
O5 C5 C4 121.21(14) . . ?
C6 C5 C4 120.17(14) . . ?
N1 C6 C5 120.46(15) . . ?
N1 C6 H6 119.8 . . ?
C5 C6 H6 119.8 . . ?
O8 C7 C2 112.54(13) . . ?
O8 C7 H7A 109.1 . . ?
C2 C7 H7A 109.1 . . ?
O8 C7 H7B 109.1 . . ?
C2 C7 H7B 109.1 . . ?
H7A C7 H7B 107.8 . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C6 N1 C2 C3 -0.4(2) . . . . ?
C6 N1 C2 C7 -179.67(14) . . . . ?
N1 C2 C3 C4 -2.6(2) . . . . ?
C7 C2 C3 C4 176.59(15) . . . . ?
C2 C3 C4 O4 -176.71(15) . . . . ?
C2 C3 C4 C5 3.9(2) . . . . ?
O4 C4 C5 O5 -1.0(2) . . . . ?
C3 C4 C5 O5 178.43(14) . . . . ?
O4 C4 C5 C6 178.20(15) . . . . ?
C3 C4 C5 C6 -2.4(2) . . . . ?
C2 N1 C6 C5 1.9(2) . . . . ?
O5 C5 C6 N1 178.78(14) . . . . ?
C4 C5 C6 N1 -0.4(2) . . . . ?
N1 C2 C7 O8 -31.0(2) . . . . ?
C3 C2 C7 O8 149.74(15) . . . . ?

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
O5 H5A O4 0.84 2.36 2.7806(16) 111.9 .
O5 H5A O8 0.84 1.95 2.7270(16) 152.4 2_564
O8 H8A O4 0.84 1.83 2.6674(16) 177.4 4_655
N1 H1A O4 0.88 1.87 2.7029(17) 156.1 2_565
C6 H6 O4 0.95 2.51 3.399(2) 156.0 4

_refine_diff_density_max         0.251
_refine_diff_density_min         -0.186
_refine_diff_density_rms         0.041

_shelxl_version_number           2013-3

_shelx_res_file                  
;
TITL C842 = 15jnac842 = L11 in P2(1)2(1)2(1), Mo, -173, 14/07/2014
CELL  0.71073    6.8410    7.0291   12.6402    90.000    90.000    90.000
ZERR  4          0.0004    0.0003    0.0004     0.000     0.000     0.000
LATT  -1
SYMM     0.50000 - X ,            - Y ,    0.50000 + Z
SYMM     0.50000 + X ,    0.50000 - Y ,            - Z
SYMM             - X ,    0.50000 + Y ,    0.50000 - Z
SFAC     C    H   N   O
UNIT    24   28   4  12
EQIV $1 -x+1/2, -y+1, z-1/2
EQIV $2 -x+1, y+1/2, -z+1/2
EQIV $3 -x+1/2, -y+1, z+1/2
EQIV $4 -x, y+1/2, -z+1/2
BOND $H
CONF
HTAB
HTAB O5 O4
HTAB O5 O8_$1
HTAB O8 O4_$2
HTAB N1 O4_$3
HTAB C6 O4_$4
MERG 2
FMAP 2
L.S. 10
PLAN -10
MPLA 6 N1 C2 C3 C4 C5 C6 O5 O6 C7
ACTA
SIZE 0.10 0.10 0.10
TEMP  -173
WGHT    0.032400    0.175000
FVAR       1.02857
O4    4    0.231887    0.342586    0.090515    11.00000    0.01829    0.01453 =
         0.00971   -0.00091   -0.00027    0.00188
O5    4   -0.063121    0.533339    0.198444    11.00000    0.01360    0.02451 =
         0.01330   -0.00502   -0.00275    0.00534
AFIX   3
H5A   2   -0.059721    0.502389    0.134284    11.00000   -1.50000
AFIX   0
O8    4    0.670928    0.506315    0.491920    11.00000    0.01640    0.01505 =
         0.01092    0.00006   -0.00024   -0.00281
AFIX   3
H8A   2    0.699698    0.611295    0.464240    11.00000   -1.50000
AFIX   0
N1    3    0.309732    0.497314    0.397405    11.00000    0.01291    0.01269 =
         0.00961   -0.00017    0.00031   -0.00104
AFIX   3
H1A   2    0.323672    0.527364    0.464575    11.00000   -1.20000
AFIX   0
C2    1    0.457987    0.410001    0.346873    11.00000    0.01225    0.01014 =
         0.01364    0.00162    0.00055   -0.00022
C3    1    0.438276    0.361048    0.242364    11.00000    0.01257    0.01088 =
         0.01387   -0.00082    0.00290    0.00058
AFIX   3
H3    2    0.545330    0.304281    0.206375    11.00000   -1.20000
AFIX   0
C4    1    0.261359    0.393553    0.187140    11.00000    0.01517    0.00899 =
         0.01143    0.00177    0.00179   -0.00074
C5    1    0.110425    0.490904    0.244492    11.00000    0.01198    0.01183 =
         0.01383    0.00093    0.00039   -0.00009
C6    1    0.138775    0.540512    0.347593    11.00000    0.01114    0.01355 =
         0.01422   -0.00096    0.00214    0.00067
AFIX   3
H6    2    0.038632    0.605666    0.384989    11.00000   -1.20000
AFIX   0
C7    1    0.639162    0.369145    0.411261    11.00000    0.01429    0.01375 =
         0.01409   -0.00125   -0.00220    0.00225
AFIX   3
H7A   2    0.626776    0.241769    0.444004    11.00000   -1.20000
H7B   2    0.754023    0.366676    0.363638    11.00000   -1.20000
AFIX   0
HKLF 4

REM  C842 = 15jnac842 = L11 in P2(1)2(1)2(1), Mo, -173, 14/07/2014
REM R1 =  0.0264 for    1346 Fo > 4sig(Fo)  and  0.0278 for all    1390 data
REM     91 parameters refined using      0 restraints

END

WGHT      0.0324      0.1751

REM Instructions for potential hydrogen bonds
HTAB O5 O4
HTAB O5 O8_$1
HTAB O8 O4_$2
HTAB N1 O4_$3
HTAB C6 O4_$4

REM Highest difference peak  0.251,  deepest hole -0.186,  1-sigma level  0.041
Q1    1   0.1879  0.4477  0.2187  11.00000  0.05    0.25
Q2    1   0.3372  0.3623  0.2221  11.00000  0.05    0.22
Q3    1   0.5427  0.3773  0.3773  11.00000  0.05    0.20
Q4    1   0.1155  0.4632  0.3014  11.00000  0.05    0.20
Q5    1   0.4265  0.3387  0.3029  11.00000  0.05    0.15
Q6    1   0.0698  0.7027  0.0652  11.00000  0.05    0.15
Q7    1   0.2416  0.5373  0.3611  11.00000  0.05    0.15
Q8    1   0.1013  0.7014  0.4185  11.00000  0.05    0.14
Q9    1   0.3724  0.4362  0.3747  11.00000  0.05    0.14
Q10   1   0.1093  0.3172  0.0771  11.00000  0.05    0.13
;
_shelx_res_checksum              42328
