# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2020

####################################################################### 
# 
# 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_8HQ_HAR_neutron
_database_code_depnum_ccdc_archive 'CCDC 1987762'
loop_
_audit_author_name
_audit_author_address
'Simon Grabowsky'
;University of Bern
Switzerland
;
_audit_update_record             
;
2020-03-10 deposited with the CCDC.	2020-06-15 downloaded from the CCDC.
;

_audit_creation_date             2019-04-29T17:55:48-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_common            '8-hydroxyquinolinium hydrogen maleate'
_chemical_formula_moiety         'C9 H8 N O, C4 H3 O4'
_chemical_formula_sum            'C13 H11 N O5'
_chemical_formula_weight         261.2363
_chemical_absolute_configuration syn

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   'p 21 21 21'
_symmetry_space_group_name_Hall  'p 2ac 2ab'
_symmetry_Int_Tables_number      19
loop_
_symmetry_equiv_pos_as_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                   5.33860(10)
_cell_length_b                   9.9878(2)
_cell_length_c                   22.3493(4)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1191.68(4)
_cell_formula_units_Z            4
_cell_measurement_temperature    15(2)
_cell_measurement_reflns_used    100369
_cell_measurement_theta_min      0.91
_cell_measurement_theta_max      26.19
_cell_measurement_wavelength     0.35307

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       needle
_exptl_crystal_colour            yellow
_exptl_crystal_size_max          0.119
_exptl_crystal_size_mid          0.092
_exptl_crystal_size_min          0.066
_exptl_crystal_density_diffrn    1.456
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             544

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.038
_exptl_absorpt_correction_type   none
_shelx_estimated_absorpt_T_min   0.995
_shelx_estimated_absorpt_T_max   0.997

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   SPring-8
_diffrn_ambient_temperature      15(2)
_diffrn_radiation_wavelength     0.35307
_diffrn_radiation_type           synchrotron
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'SPring-8 BL02B1 Curved Imaging Plate'
_diffrn_detector_area_resol_mean 10
_diffrn_orient_matrix_type       fs_process
_diffrn_orient_matrix_ub_11      0.183986
_diffrn_orient_matrix_ub_12      0.006502
_diffrn_orient_matrix_ub_13      0.007879
_diffrn_orient_matrix_ub_21      -0.024343
_diffrn_orient_matrix_ub_22      0.091336
_diffrn_orient_matrix_ub_23      0.017382
_diffrn_orient_matrix_ub_31      -0.025364
_diffrn_orient_matrix_ub_32      -0.040496
_diffrn_orient_matrix_ub_33      0.04047
_diffrn_measurement_device       'quarter Χ-circle diffractometer'
_diffrn_measurement_device_type  IPDSC-Q
_diffrn_measurement_method       'phi or omega oscillation scans'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_reflns_av_R_equivalents  0.0522
_diffrn_reflns_av_unetI/netI     0.0328
_diffrn_reflns_number            80044
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -21
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_l_min       -51
_diffrn_reflns_limit_l_max       50
_diffrn_reflns_theta_min         0.905
_diffrn_reflns_theta_max         24.239
_diffrn_reflns_theta_full        12.23
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.996
_reflns_Friedel_fraction_full    1
_reflns_Friedel_fraction_max     0.995
_reflns_Friedel_coverage         0.809
_reflns_number_total             15641
_reflns_number_gt                12569
_reflns_threshold_expression     'F>0 & F/u(F)>4.0 & |F_calc|>10^-3'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'CrystalClear (Rigaku/MSC Inc., 2006)'
_computing_cell_refinement       'CrystalClear (Rigaku/MSC Inc., 2006)'
_computing_data_reduction        
'CrystalClear (Rigaku/MSC Inc., 2006), SORTAV (Blessing, 1995)'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2014)'
_computing_structure_refinement  
'Tonto 18.12.17 github v. 2b3dd9c (Capelli, 2014)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     dual
_atom_sites_solution_hydrogens   difmap

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
  .  Hirshfeld atom refinement:
     .  Uses aspherical atomic scattering factors
        obtained from Hirshfeld partitioning of a
        gaussian quantum chemical wavefunction.
     .  Hirshfeld weight functions obtained from
        spherically averaged unrestricted atomic
        densities.
  .  Wavefunction type : rhf using 8A SC cluster charges, 
  .  Gaussian basis set: def2-TZVP
  .  Refinement based on |F| with weight=1/sigma(|F|)
  .  Negative |F|^^2 were pruned from the data
  .  |F| < 4.0 sigma(|F|) were pruned from the data
  .  Eigenvalues < 0.1E-04 removed from normal equations
  .  Reflection used in the refinement appear below
  .  Refined using the Tonto program
  . If constraints were applied they are defined by zero
  eigenvalues of the least-squares hessian, see the
  value of _refine_ls_SVD_threshold
;
_refine_ls_structure_factor_coef F
_refine_ls_coordinate_system     cartesian
_refine_ls_SVD_threshold         0.1E-02
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      sigma
_refine_ls_weighting_details     w=1/σ(F)
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_extinction_method     none
_refine_ls_number_reflns         12569
_refine_ls_number_parameters     205
_refine_ls_number_restraints     0
_refine_ls_number_constraints    66
_refine_ls_R_factor_all          0.0334
_refine_ls_R_factor_gt           0.0334
_refine_ls_wR_factor_gt          0.0207
_refine_ls_wR_factor_all         0.0207
_refine_ls_goodness_of_fit_gt    1.6975
_refine_ls_goodness_of_fit_all   1.6975
_refine_ls_shift/su_max          0.0057
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 
;
 Flack x determined using 4959 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(6)
_refine_diff_density_max         0.3144
_refine_diff_density_min         -0.2951
_refine_diff_density_rms         0.0473

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0 0 'Hirshfeld partitioning of a quantum chemical wavefunction.'
H H 0 0 'Hirshfeld partitioning of a quantum chemical wavefunction.'
N N 0 0 'Hirshfeld partitioning of a quantum chemical wavefunction.'
O O 0 0 'Hirshfeld partitioning of a quantum chemical wavefunction.'

loop_
_atom_site_label
_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_disorder_group
C1 0.58580(6) 0.67792(3) 0.596512(13) 0.01173(12) Uani 1 0
C2 0.73554(6) 0.64408(3) 0.541921(13) 0.01136(11) Uani 1 0
C3 0.93464(6) 0.56292(3) 0.534640(13) 0.01113(12) Uani 1 0
C4 1.07532(6) 0.48126(3) 0.579637(12) 0.00992(11) Uani 1 0
C6 0.79190(6) 0.16236(3) 0.589282(13) 0.01156(12) Uani 1 0
C7 0.98022(7) 0.06751(4) 0.586769(14) 0.01547(14) Uani 1 0
C8 1.09172(7) 0.01802(4) 0.639815(15) 0.01711(14) Uani 1 0
C9 1.02023(7) 0.06442(4) 0.695349(15) 0.01510(14) Uani 1 0
C10 0.82756(6) 0.16175(3) 0.699636(13) 0.01096(11) Uani 1 0
C5 0.71218(6) 0.20837(3) 0.646393(13) 0.00992(11) Uani 1 0
C13 0.44209(6) 0.34827(3) 0.701760(13) 0.01113(11) Uani 1 0
C12 0.55043(6) 0.30736(3) 0.755731(13) 0.01186(12) Uani 1 0
C11 0.74137(7) 0.21442(3) 0.754731(13) 0.01202(11) Uani 1 0
N1 0.52240(5) 0.29949(3) 0.649870(11) 0.00981(10) Uani 1 0
O5 0.67659(5) 0.21631(3) 0.541753(10) 0.01416(10) Uani 1 0
O4 1.25526(5) 0.41266(2) 0.559762(10) 0.01202(9) Uani 1 0
O2 1.01598(5) 0.48365(3) 0.634425(10) 0.01266(10) Uani 1 0
O3 0.41184(5) 0.75672(3) 0.592038(11) 0.01713(11) Uani 1 0
O1 0.64305(5) 0.62230(3) 0.647781(10) 0.01462(10) Uani 1 0
H8 1.1135(12) 0.0272(6) 0.7357(2) 0.02506667 Uani 1 0
H7 1.2380(12) -0.0595(6) 0.6357(3) 0.02656667 Uani 1 0
H6 1.0472(11) 0.0323(6) 0.5441(2) 0.0256 Uani 1 0
H5 0.7293(14) 0.1681(7) 0.5043(3) 0.0214 Uani 1 0
H4 0.4283(13) 0.3356(7) 0.6102(3) 0.0187 Uani 1 0
H9 0.8265(11) 0.1795(6) 0.7960(2) 0.0235333 Uani 1 0
H10 0.4785(11) 0.3467(5) 0.7977(2) 0.0225333 Uani 1 0
H11 0.2822(11) 0.4165(5) 0.6986(3) 0.0222333 Uani 1 0
H1 0.8089(16) 0.5610(8) 0.6438(3) 0.0190333 Uani 1 0
H2 0.6690(11) 0.6980(6) 0.5018(2) 0.0231 Uani 1 0
H3 1.0136(12) 0.5580(6) 0.4897(2) 0.0215667 Uani 1 0



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O5 C6 1.3407(4) . . yes
O4 C4 1.2608(4) . . yes
O2 C4 1.2650(4) . . yes
O3 C1 1.2215(4) . . yes
O1 C1 1.3095(4) . . yes
O5 H5 1.006(6) . . yes
O1 H1 1.080(9) . . yes
N1 C5 1.3641(4) . . yes
N1 C13 1.3289(4) . . yes
N1 H4 1.082(6) . . yes
C1 C2 1.4973(4) . . yes
C2 C3 1.3466(5) . . yes
C3 C4 1.4968(4) . . yes
C6 C7 1.3826(5) . . yes
C6 C5 1.4218(4) . . yes
C7 C8 1.4157(5) . . yes
C8 C9 1.3787(5) . . yes
C9 C10 1.4185(5) . . yes
C10 C5 1.4185(4) . . yes
C10 C11 1.4159(4) . . yes
C13 C12 1.3987(4) . . yes
C12 C11 1.3789(5) . . yes
C2 H2 1.104(5) . . yes
C3 H3 1.090(5) . . yes
C7 H6 1.078(5) . . yes
C8 H7 1.104(6) . . yes
C9 H8 1.096(5) . . yes
C13 H11 1.095(5) . . yes
C12 H10 1.086(5) . . yes
C11 H9 1.085(5) . . yes

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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O4 C4 O2 122.82(3) . . . yes
O3 C1 O1 121.49(3) . . . yes
O5 C6 C7 125.25(3) . . . yes
O5 C6 C5 116.36(3) . . . yes
O4 C4 C3 116.21(3) . . . yes
O2 C4 C3 120.96(3) . . . yes
O3 C1 C2 118.99(3) . . . yes
O1 C1 C2 119.51(3) . . . yes
N1 C5 C6 119.28(3) . . . yes
N1 C5 C10 119.59(3) . . . yes
N1 C13 C12 120.80(3) . . . yes
N1 C13 H11 115.0(3) . . . yes
C1 O1 H1 111.1(4) . . . yes
C6 O5 H5 109.8(4) . . . yes
C5 N1 C13 122.27(3) . . . yes
C5 N1 H4 121.4(3) . . . yes
C13 N1 H4 116.3(3) . . . yes
C1 C2 C3 130.98(3) . . . yes
C2 C3 C4 130.00(3) . . . yes
C6 C7 C8 120.73(3) . . . yes
C6 C5 C10 121.13(3) . . . yes
C7 C6 C5 118.40(3) . . . yes
C7 C8 C9 121.34(3) . . . yes
C8 C9 C10 119.46(3) . . . yes
C9 C10 C5 118.89(3) . . . yes
C9 C10 C11 123.30(3) . . . yes
C10 C11 C12 120.30(3) . . . yes
C5 C10 C11 117.80(3) . . . yes
C13 C12 C11 119.23(3) . . . yes
C1 C2 H2 112.3(3) . . . yes
C2 C3 H3 116.3(3) . . . yes
C3 C2 H2 116.7(3) . . . yes
C4 C3 H3 113.6(3) . . . yes
C6 C7 H6 120.0(3) . . . yes
C7 C8 H7 118.2(3) . . . yes
C8 C7 H6 119.2(3) . . . yes
C8 C9 H8 120.1(3) . . . yes
C9 C8 H7 120.5(3) . . . yes
C10 C9 H8 120.4(3) . . . yes
C10 C11 H9 118.9(3) . . . yes
C13 C12 H10 119.5(3) . . . yes
C12 C13 H11 124.1(3) . . . yes
C12 C11 H9 120.8(3) . . . yes
C11 C12 H10 121.3(3) . . . yes

#----------------------------------------------------------------------------#
#                   TONTO INSTRUCTION FILE                                   #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   TONTO REFLECTION FILE                                    #
#----------------------------------------------------------------------------#

# start Validation Reply Form
_vrf_PLAT353_8HQ_HAR_neutron     
;
PROBLEM: Long   N-H (N0.87,N1.01A)  N1       - H4       .       1.08 Ang.  
RESPONSE: This is the correct N-H bond length, very close to the reference value
from neutron diffraction. It proves that our non-spherical quantum crystallographic
refinement gives correct results. This should not be an alert.
;
# end Validation Reply Form


# END of CIF
####################################################################### 
# 
# 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_K_HAR_neutron
_database_code_depnum_ccdc_archive 'CCDC 1989533'
loop_
_audit_author_name
_audit_author_address
'Simon Grabowsky'
;University of Bern
Switzerland
;
_audit_update_record             
;
2020-03-10 deposited with the CCDC.	2020-06-15 downloaded from the CCDC.
;

_audit_creation_date             2019-04-30T12:51:47-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_common            'Potassium hydrogen maleate'
_chemical_formula_moiety         'C4 H3 O4, K'
_chemical_formula_sum            'C4 H3 K O4'
_chemical_formula_weight         154.16
_chemical_absolute_configuration syn

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           Orthorhombic
_symmetry_space_group_name_H-M   'p b c m'
_symmetry_space_group_name_Hall  '-p 2c 2b'
_symmetry_Int_Tables_number      57
loop_
_symmetry_equiv_pos_as_xyz
'+x, +y, +z'
'-x, -y, -z'
'-x, -y, +z+1/2'
'+x, -y+1/2, -z'
'+x, +y, -z+1/2'
'-x, +y+1/2, +z'
'-x, +y+1/2, -z+1/2'
'+x, -y+1/2, +z+1/2'

_cell_length_a                   4.50760(10)
_cell_length_b                   7.70270(10)
_cell_length_c                   15.9229(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     552.854(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    15(2)
_cell_measurement_reflns_used    111452
_cell_measurement_theta_min      1.27
_cell_measurement_theta_max      60.64
_cell_measurement_wavelength     0.3531

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       platelet
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.15
_exptl_crystal_size_min          0.05
_exptl_crystal_density_diffrn    1.852
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             312

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.141
_exptl_absorpt_correction_type   none
_shelx_estimated_absorpt_T_min   0.979
_shelx_estimated_absorpt_T_max   0.993

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   SPring-8
_diffrn_ambient_temperature      15(2)
_diffrn_radiation_wavelength     0.3531
_diffrn_radiation_type           synchrotron
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'SPring-8 BL02B1 Curved Imaging Plate'
_diffrn_detector_area_resol_mean 10
_diffrn_orient_matrix_type       fs_process
_diffrn_measurement_device       'quarter Χ-circle diffractometer'
_diffrn_measurement_device_type  IPDSC-Q
_diffrn_measurement_method       'phi or omega oscillation scans'
_diffrn_standards_number         0
_diffrn_reflns_av_R_equivalents  0.0422
_diffrn_reflns_av_unetI/netI     0.0124
_diffrn_reflns_number            86584
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_limit_l_max       41
_diffrn_reflns_theta_min         1.271
_diffrn_reflns_theta_max         27.684
_diffrn_reflns_theta_full        12.231
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 1
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 1
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 1
_reflns_Friedel_coverage         0
_reflns_number_total             5365
_reflns_number_gt                4972
_reflns_threshold_expression     'F>0 & F/u(F)>4.0 & |F_calc|>10^-3'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'CrystalClear (Rigaku/MSC Inc., 2006)'
_computing_cell_refinement       'CrystalClear (Rigaku/MSC Inc., 2006)'
_computing_data_reduction        
'CrystalClear (Rigaku/MSC Inc., 2006), SORTAV (Blessing, 1995)'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2014)'
_computing_structure_refinement  
'Tonto 18.12.17 github v. 2b3dd9c (Capelli, 2014)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     dual
_atom_sites_solution_hydrogens   difmap

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
  .  Hirshfeld atom refinement:
     .  Uses aspherical atomic scattering factors
        obtained from Hirshfeld partitioning of a
        gaussian quantum chemical wavefunction.
     .  Hirshfeld weight functions obtained from
        spherically averaged unrestricted atomic
        densities.
  .  Wavefunction type : rhf using 8A SC cluster charges, 
  .  Gaussian basis set: def2-TZVP
  .  Refinement based on |F| with weight=1/sigma(|F|)
  .  Negative |F|^^2 were pruned from the data
  .  |F| < 4.0 sigma(|F|) were pruned from the data
  .  Eigenvalues < 0.1E-04 removed from normal equations
  .  Reflection used in the refinement appear below
  .  Refined using the Tonto program
  . If constraints were applied they are defined by zero
  eigenvalues of the least-squares hessian, see the
  value of _refine_ls_SVD_threshold
;
_refine_ls_structure_factor_coef F
_refine_ls_coordinate_system     cartesian
_refine_ls_SVD_threshold         0.1E-02
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      sigma
_refine_ls_weighting_details     w=1/σ(F)
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_extinction_method     none
_refine_ls_number_reflns         4972
_refine_ls_number_parameters     51
_refine_ls_number_restraints     0
_refine_ls_number_constraints    13
_refine_ls_R_factor_all          0.0212
_refine_ls_R_factor_gt           0.0212
_refine_ls_wR_factor_gt          0.0213
_refine_ls_wR_factor_all         0.0213
_refine_ls_goodness_of_fit_gt    2.9351
_refine_ls_goodness_of_fit_all   2.9351
_refine_ls_shift/su_max          0.0056
_refine_diff_density_max         0.4832
_refine_diff_density_min         -0.367
_refine_diff_density_rms         0.0412

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0 0 'Hirshfeld partitioning of a quantum chemical wavefunction.'
O O 0 0 'Hirshfeld partitioning of a quantum chemical wavefunction.'
H H 0 0 'Hirshfeld partitioning of a quantum chemical wavefunction.'
K K 0 0 'Hirshfeld partitioning of a quantum chemical wavefunction.'

loop_
_atom_site_label
_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_disorder_group
K1 0.761154(10) 0.250(4) 0.500(2) 0.006923(19) Uani 1 0
O3 1.26419(3) 0.080667(17) 0.428980(8) 0.00887(4) Uani 1 0
O1 1.01050(3) 0.205634(16) 0.326205(7) 0.00868(4) Uani 1 0
C1 1.21697(3) 0.103748(19) 0.353062(9) 0.00668(4) Uani 1 0
C2 1.41260(3) 0.010464(18) 0.292175(8) 0.00754(4) Uani 1 0
H2 1.5830(9) -0.0678(6) 0.3232(3) 0.02073333 Uani 1 0
H1 1.0037(16) 0.2116(10) 0.25 0.0188667 Uani 1 0



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
K1 O3 2.85(2) . . yes
K1 O1 3.01(4) . . yes
O3 C1 1.2402(2) . . yes
O1 C1 1.2903(2) . . yes
O1 H1 1.2146(3) . . yes
C1 C2 1.4946(2) . . yes
C2 H2 1.094(4) . . yes

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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
K1 O3 C1 100.6(7) . . . yes
K1 O1 C1 91.9(4) . . . yes
K1 O1 H1 154.9(5) . . . yes
O3 K1 O1 44.4(5) . . . yes
O3 C1 O1 122.276(14) . . . yes
O3 C1 C2 117.521(13) . . . yes
O1 C1 C2 120.197(12) . . . yes
C1 O1 H1 111.8(3) . . . yes
C1 C2 H2 112.7(2) . . . yes

#----------------------------------------------------------------------------#
#                   TONTO INSTRUCTION FILE                                   #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   TONTO REFLECTION FILE                                    #
#----------------------------------------------------------------------------#

# start Validation Reply Form
_vrf_PLAT974_K_HAR_neutron       
;
PROBLEM: Check Calcd Negative Resid. Density on        K1      -2.75 eA-3  
RESPONSE: This is not true. When we use the structure factors calculated 
by the non-spherical Hirshfeld model that was used in the refinement, 
there is no such negative residual density.
;
_vrf_PLAT924_K_HAR_neutron       
;
PROBLEM: The Reported and Calculated Rho(min) Differ by .       2.38 eA-3  
RESPONSE: This is not true. When we use the structure factors calculated
by the non-spherical Hirshfeld model that was used in the refinement, 
there is no such negative residual density.
;
# end Validation Reply Form


# END of CIF
####################################################################### 
# 
# 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_Li_HAR_neutron
_database_code_depnum_ccdc_archive 'CCDC 1989516'
loop_
_audit_author_name
_audit_author_address
'Simon Grabowsky'
;University of Bern
Switzerland
;
_audit_update_record             
;
2020-03-10 deposited with the CCDC.	2020-06-15 downloaded from the CCDC.
;

_audit_creation_date             2019-04-30T17:40:19-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_common            'Lithium hydrogen maleate dihydrate'
_chemical_formula_moiety         'C4 H3 O4, Li, 2(H2 O)'
_chemical_formula_sum            'C4 H7 Li O6'
_chemical_formula_weight         158.0358
_chemical_absolute_configuration .

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'p 1 21/n 1'
_symmetry_space_group_name_Hall  '-p 2yn'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'+x, +y, +z'
'-x, -y, -z'
'-x+1/2, +y+1/2, -z+1/2'
'+x+1/2, -y+1/2, +z+1/2'

_cell_length_a                   5.83310(10)
_cell_length_b                   5.94390(10)
_cell_length_c                   18.7920(4)
_cell_angle_alpha                90
_cell_angle_beta                 91.3050(10)
_cell_angle_gamma                90
_cell_volume                     651.38(2)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    8603
_cell_measurement_theta_min      19.82
_cell_measurement_theta_max      52.15
_cell_measurement_wavelength     0.71073

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.215
_exptl_crystal_size_mid          0.213
_exptl_crystal_size_min          0.171
_exptl_crystal_density_diffrn    1.612
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             328

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.152
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_absorpt_correction_T_min  0.699
_exptl_absorpt_correction_T_max  0.752

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   'sealed x-ray tube'
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'APEX-II CCD'
_diffrn_orient_matrix_ub_11      0.103298
_diffrn_orient_matrix_ub_12      -0.000761
_diffrn_orient_matrix_ub_13      0.043161
_diffrn_orient_matrix_ub_21      0.10872
_diffrn_orient_matrix_ub_22      -0.101465
_diffrn_orient_matrix_ub_23      -0.024906
_diffrn_orient_matrix_ub_31      0.082885
_diffrn_orient_matrix_ub_32      0.13404
_diffrn_orient_matrix_ub_33      -0.018608
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II'
_diffrn_measurement_method       'φ or ω oscillation scans'
_diffrn_standards_number         0
_diffrn_reflns_av_R_equivalents  0.0302
_diffrn_reflns_av_unetI/netI     0.0119
_diffrn_reflns_number            99272
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -41
_diffrn_reflns_limit_l_max       40
_diffrn_reflns_theta_min         2.168
_diffrn_reflns_theta_max         52.306
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_reflns_Friedel_coverage         0
_reflns_number_total             7520
_reflns_number_gt                6436
_reflns_threshold_expression     'F>0 & F/u(F)>4.0 & |F_calc|>10^-3'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'CrystalClear (Rigaku/MSC Inc., 2006)'
_computing_cell_refinement       'CrystalClear (Rigaku/MSC Inc., 2006)'
_computing_data_reduction        
'CrystalClear (Rigaku/MSC Inc., 2006), SORTAV (Blessing, 1995)'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2014)'
_computing_structure_refinement  
'Tonto 18.12.17 github v. 2b3dd9c (Capelli, 2014)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     dual
_atom_sites_solution_hydrogens   difmap

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
  .  Hirshfeld atom refinement:
     .  Uses aspherical atomic scattering factors
        obtained from Hirshfeld partitioning of a
        gaussian quantum chemical wavefunction.
     .  Hirshfeld weight functions obtained from
        spherically averaged unrestricted atomic
        densities.
  .  Wavefunction type : rhf using 8A SC cluster charges, 
  .  Gaussian basis set: def2-TZVP
  .  Refinement based on |F| with weight=1/sigma(|F|)
  .  Negative |F|^^2 were pruned from the data
  .  |F| < 4.0 sigma(|F|) were pruned from the data
  .  Eigenvalues < 0.1E-04 removed from normal equations
  .  Reflection used in the refinement appear below
  .  Refined using the Tonto program
  . If constraints were applied they are defined by zero
  eigenvalues of the least-squares hessian, see the
  value of _refine_ls_SVD_threshold
;
_refine_ls_structure_factor_coef F
_refine_ls_coordinate_system     cartesian
_refine_ls_SVD_threshold         0.1E-02
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      sigma
_refine_ls_weighting_details     w=1/σ(F)
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_extinction_method     none
_refine_ls_number_reflns         6436
_refine_ls_number_parameters     121
_refine_ls_number_restraints     0
_refine_ls_number_constraints    42
_refine_ls_R_factor_all          0.0195
_refine_ls_R_factor_gt           0.0195
_refine_ls_wR_factor_gt          0.016
_refine_ls_wR_factor_all         0.016
_refine_ls_goodness_of_fit_gt    2.4666
_refine_ls_goodness_of_fit_all   2.4666
_refine_ls_shift/su_max          0.0091
_refine_diff_density_max         0.1573
_refine_diff_density_min         -0.2317
_refine_diff_density_rms         0.0395

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0 0 'Hirshfeld partitioning of a quantum chemical wavefunction.'
H H 0 0 'Hirshfeld partitioning of a quantum chemical wavefunction.'
Li Li 0 0 'Hirshfeld partitioning of a quantum chemical wavefunction.'
O O 0 0 'Hirshfeld partitioning of a quantum chemical wavefunction.'

loop_
_atom_site_label
_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_disorder_group
O2 0.450372(18) 0.755490(18) 0.569606(6) 0.00876(4) Uani 1 0
O1 0.365862(18) 0.749276(18) 0.442438(6) 0.00890(4) Uani 1 0
O6 0.692400(19) 0.787816(19) 0.190901(6) 0.00932(4) Uani 1 0
O3 0.55856(2) 0.73020(2) 0.343314(6) 0.01095(4) Uani 1 0
O4 0.75649(2) 0.74980(2) 0.641308(6) 0.01246(4) Uani 1 0
O5 1.09208(2) 0.73566(2) 0.279314(7) 0.01592(5) Uani 1 0
C4 0.66818(2) 0.75280(2) 0.580781(7) 0.00782(4) Uani 1 0
C2 0.78123(2) 0.74984(2) 0.448727(8) 0.00928(5) Uani 1 0
C1 0.55707(2) 0.74269(2) 0.408846(8) 0.00774(4) Uani 1 0
C3 0.82656(2) 0.75334(2) 0.519176(8) 0.00905(4) Uani 1 0
Li1 0.78599(6) 0.61579(5) 0.277730(18) 0.01287(13) Uani 1 0
H3 1.0073(6) 0.7569(5) 0.5359(2) 0.03576206 Uani 1 0
H6 0.7917(8) 0.7630(6) 0.1514(2) 0.03237118 Uani 1 0
H7 0.5354(8) 0.7630(7) 0.1725(3) 0.03168378 Uani 1 0
H2 0.9275(6) 0.7505(5) 0.4123(2) 0.0344224 Uani 1 0
H5 1.1493(9) 0.7497(7) 0.2316(2) 0.0383628 Uani 1 0
H4 1.2292(8) 0.7276(7) 0.3089(3) 0.0429472 Uani 1 0
H1 0.3964(8) 0.7539(6) 0.5005(3) 0.0287944 Uani 1 0



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O2 C4 1.28312(17) . . yes
O1 C1 1.29465(18) . . yes
O3 C1 1.23393(18) . . yes
O4 C4 1.23802(17) . . yes
O6 Li1 1.9913(3) . . yes
O3 Li1 1.9534(3) . . yes
O5 Li1 1.9220(4) . . yes
O1 H1 1.101(6) . . yes
O6 H6 0.963(4) . . yes
O6 H7 0.982(4) . . yes
O5 H5 0.967(5) . . yes
O5 H4 0.965(4) . . yes
C4 C3 1.4975(2) . . yes
C2 C1 1.49279(19) . . yes
C2 C3 1.3443(2) . . yes
C2 H2 1.106(4) . . yes
C3 H3 1.093(4) . . yes

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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O2 C4 O4 122.703(14) . . . yes
O1 C1 O3 120.941(13) . . . yes
O2 C4 C3 119.963(12) . . . yes
O1 C1 C2 120.584(13) . . . yes
O3 C1 C2 118.474(13) . . . yes
O4 C4 C3 117.333(12) . . . yes
O6 Li1 O3 99.253(15) . . . yes
O6 Li1 O5 93.416(15) . . . yes
O3 Li1 O5 120.343(18) . . . yes
C1 O3 Li1 132.140(14) . . . yes
C1 O1 H1 111.2(3) . . . yes
C4 C3 C2 130.566(13) . . . yes
C1 C2 C3 130.187(13) . . . yes
C4 C3 H3 112.7(2) . . . yes
C2 C3 H3 116.7(2) . . . yes
C1 C2 H2 111.6(2) . . . yes
C3 C2 H2 118.2(2) . . . yes
Li1 O6 H6 113.2(3) . . . yes
Li1 O6 H7 116.5(3) . . . yes
Li1 O5 H5 110.9(3) . . . yes
Li1 O5 H4 138.4(3) . . . yes
H6 O6 H7 106.1(4) . . . yes
H5 O5 H4 103.9(4) . . . yes

#----------------------------------------------------------------------------#
#                   TONTO INSTRUCTION FILE                                   #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   TONTO REFLECTION FILE                                    #
#----------------------------------------------------------------------------#

# END of CIF
####################################################################### 
# 
# 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_Na_HAR_neutron
_database_code_depnum_ccdc_archive 'CCDC 1989518'
loop_
_audit_author_name
_audit_author_address
'Simon Grabowsky'
;University of Bern
Switzerland
;
_audit_update_record             
;
2020-03-10 deposited with the CCDC.	2020-06-15 downloaded from the CCDC.
;

_audit_creation_date             2019-05-02T13:25:16-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_common            'Sodium hydrogen maleate trihydrate'
_chemical_formula_moiety         'C4 H3 O4, Na, 3(H2 O)'
_chemical_formula_sum            'C4 H9 Na O7'
_chemical_formula_weight         192.1019
_chemical_absolute_configuration .

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           Triclinic
_symmetry_space_group_name_H-M   'p -1'
_symmetry_space_group_name_Hall  '-p 1'
_symmetry_Int_Tables_number      2
loop_
_symmetry_equiv_pos_as_xyz
'+x, +y, +z'
'-x, -y, -z'

_cell_length_a                   5.9224(4)
_cell_length_b                   6.2512(3)
_cell_length_c                   11.2141(7)
_cell_angle_alpha                103.935(7)
_cell_angle_beta                 91.490(6)
_cell_angle_gamma                99.823(7)
_cell_volume                     396.07(4)
_cell_formula_units_Z            2
_cell_measurement_temperature    15(2)
_cell_measurement_reflns_used    28744
_cell_measurement_theta_min      0.93
_cell_measurement_theta_max      30.3
_cell_measurement_wavelength     0.3531

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       prism
_exptl_crystal_colour            colourless
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.07
_exptl_crystal_density_diffrn    1.611
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             200

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.051
_exptl_absorpt_correction_type   none
_shelx_estimated_absorpt_T_min   0.993
_shelx_estimated_absorpt_T_max   0.996

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   SPring-8
_diffrn_ambient_temperature      15(2)
_diffrn_radiation_wavelength     0.3531
_diffrn_radiation_type           synchrotron
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'SPring-8 BL02B1 Curved Imaging Plate'
_diffrn_detector_area_resol_mean 10
_diffrn_orient_matrix_ub_11      -0.165287
_diffrn_orient_matrix_ub_12      -0.041103
_diffrn_orient_matrix_ub_13      -0.031242
_diffrn_orient_matrix_ub_21      -0.014255
_diffrn_orient_matrix_ub_22      -0.141509
_diffrn_orient_matrix_ub_23      0.028175
_diffrn_orient_matrix_ub_31      -0.044575
_diffrn_orient_matrix_ub_32      0.079906
_diffrn_orient_matrix_ub_33      0.081935
_diffrn_measurement_device       'quarter Χ-circle diffractometer'
_diffrn_measurement_device_type  IPDSC-Q
_diffrn_measurement_method       'phi or omega oscillation scans'
_diffrn_standards_number         0
_diffrn_reflns_av_R_equivalents  0.0175
_diffrn_reflns_av_unetI/netI     0.0094
_diffrn_reflns_number            70649
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         0.932
_diffrn_reflns_theta_max         26.191
_diffrn_reflns_theta_full        12.231
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.939
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.939
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.939
_reflns_Friedel_coverage         0
_reflns_number_total             12183
_reflns_number_gt                11038
_reflns_threshold_expression     'F>0 & F/u(F)>4.0 & |F_calc|>10^-3'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'CrystalClear (Rigaku/MSC Inc., 2006)'
_computing_cell_refinement       'CrystalClear (Rigaku/MSC Inc., 2006)'
_computing_data_reduction        
'CrystalClear (Rigaku/MSC Inc., 2006), SORTAV (Blessing, 1995)'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2014)'
_computing_structure_refinement  
'Tonto 18.12.17 github v. 2b3dd9c (Capelli, 2014)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     dual
_atom_sites_solution_hydrogens   difmap

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
  .  Hirshfeld atom refinement:
     .  Uses aspherical atomic scattering factors
        obtained from Hirshfeld partitioning of a
        gaussian quantum chemical wavefunction.
     .  Hirshfeld weight functions obtained from
        spherically averaged unrestricted atomic
        densities.
  .  Wavefunction type : rhf using 8A SC cluster charges, 
  .  Gaussian basis set: def2-TZVP
  .  Refinement based on |F| with weight=1/sigma(|F|)
  .  Negative |F|^^2 were pruned from the data
  .  |F| < 4.0 sigma(|F|) were pruned from the data
  .  Eigenvalues < 0.1E-04 removed from normal equations
  .  Reflection used in the refinement appear below
  .  Refined using the Tonto program
  . If constraints were applied they are defined by zero
  eigenvalues of the least-squares hessian, see the
  value of _refine_ls_SVD_threshold
;
_refine_ls_structure_factor_coef F
_refine_ls_coordinate_system     cartesian
_refine_ls_SVD_threshold         0.1E-02
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      sigma
_refine_ls_weighting_details     w=1/σ(F)
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_extinction_method     none
_refine_ls_number_reflns         11037
_refine_ls_number_parameters     136
_refine_ls_number_restraints     0
_refine_ls_number_constraints    54
_refine_ls_R_factor_all          0.0185
_refine_ls_R_factor_gt           0.0185
_refine_ls_wR_factor_gt          0.0194
_refine_ls_wR_factor_all         0.0194
_refine_ls_goodness_of_fit_gt    3.8153
_refine_ls_goodness_of_fit_all   3.8153
_refine_ls_shift/su_max          0.0096
_refine_diff_density_max         0.3431
_refine_diff_density_min         -0.4738
_refine_diff_density_rms         0.046

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0 0 'Hirshfeld partitioning of a quantum chemical wavefunction.'
H H 0 0 'Hirshfeld partitioning of a quantum chemical wavefunction.'
Na Na 0 0 'Hirshfeld partitioning of a quantum chemical wavefunction.'
O O 0 0 'Hirshfeld partitioning of a quantum chemical wavefunction.'

loop_
_atom_site_label
_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_disorder_group
Na1 0.753573(12) 0.537638(12) 0.428102(6) 0.00683(2) Uani 1 0
C2 0.71443(2) 0.28279(3) 0.077880(13) 0.00712(4) Uani 1 0
C3 0.66008(2) 0.23403(3) -0.044091(13) 0.00712(4) Uani 1 0
C4 0.80849(2) 0.19096(2) -0.150441(12) 0.00587(4) Uani 1 0
O4 0.710640(19) 0.14350(2) -0.256200(10) 0.00776(4) Uani 1 0
O2 1.023469(18) 0.20434(2) -0.131196(10) 0.00743(4) Uani 1 0
O1 1.125306(18) 0.28599(2) 0.089692(10) 0.00757(4) Uani 1 0
O3 0.94773(2) 0.36149(2) 0.260903(10) 0.00795(4) Uani 1 0
O6 0.37262(2) 0.32878(2) 0.369737(11) 0.00843(4) Uani 1 0
O7 0.85552(2) 0.25050(2) 0.515454(11) 0.00825(4) Uani 1 0
O5 0.72349(2) 0.83942(2) 0.338756(11) 0.00809(4) Uani 1 0
C1 0.94037(2) 0.31164(2) 0.147714(12) 0.00592(4) Uani 1 0
H3 0.4825(6) 0.2239(7) -0.0732(3) 0.02263232 Uani 1 0
H2 0.5760(6) 0.3087(7) 0.1399(3) 0.02150602 Uani 1 0
H6 0.2441(8) 0.3607(8) 0.3274(4) 0.02315575 Uani 1 0
H7 0.3596(9) 0.1674(7) 0.3381(5) 0.0247466 Uani 1 0
H9 0.8161(9) 0.2179(8) 0.5930(4) 0.0231818 Uani 1 0
H8 0.8217(9) 0.1067(8) 0.4547(4) 0.0219293 Uani 1 0
H4 0.5713(8) 0.8395(8) 0.3029(4) 0.0209782 Uani 1 0
H5 0.8255(8) 0.8343(8) 0.2729(4) 0.021659 Uani 1 0
H1 1.0846(9) 0.2465(9) -0.0102(5) 0.0173841 Uani 1 0



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Na1 O3 2.36645(14) . . yes
Na1 O6 2.39367(13) . . yes
Na1 O7 2.39412(14) . . yes
Na1 O5 2.36863(14) . . yes
O4 C4 1.25162(16) . . yes
O2 C4 1.27092(17) . . yes
O1 C1 1.30210(18) . . yes
O3 C1 1.22969(17) . . yes
O1 H1 1.099(5) . . yes
O6 H6 0.961(4) . . yes
O6 H7 0.974(4) . . yes
O7 H9 0.966(4) . . yes
O7 H8 0.974(4) . . yes
O5 H4 0.978(4) . . yes
O5 H5 0.964(4) . . yes
C2 C3 1.34544(19) . . yes
C2 C1 1.49378(19) . . yes
C3 C4 1.4993(2) . . yes
C2 H2 1.097(4) . . yes
C3 H3 1.080(3) . . yes

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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
Na1 O3 C1 141.722(10) . . . yes
Na1 O6 H6 131.2(3) . . . yes
Na1 O6 H7 116.1(3) . . . yes
Na1 O7 H9 128.6(3) . . . yes
Na1 O7 H8 109.8(3) . . . yes
Na1 O5 H4 115.9(3) . . . yes
Na1 O5 H5 108.3(3) . . . yes
O3 Na1 O6 99.662(5) . . . yes
O3 Na1 O7 82.403(5) . . . yes
O3 Na1 O5 92.042(5) . . . yes
O6 Na1 O7 91.234(5) . . . yes
O6 Na1 O5 98.094(5) . . . yes
O7 Na1 O5 169.848(5) . . . yes
O4 C4 O2 122.901(14) . . . yes
O1 C1 O3 120.918(12) . . . yes
O4 C4 C3 116.927(12) . . . yes
O2 C4 C3 120.171(12) . . . yes
O1 C1 C2 120.557(12) . . . yes
O3 C1 C2 118.524(13) . . . yes
C1 O1 H1 110.0(3) . . . yes
C2 C3 C4 130.360(13) . . . yes
C3 C2 C1 130.540(13) . . . yes
C2 C3 H3 117.1(2) . . . yes
C3 C2 H2 117.84(19) . . . yes
C4 C3 H3 112.6(2) . . . yes
C1 C2 H2 111.62(19) . . . yes
H6 O6 H7 102.9(4) . . . yes
H9 O7 H8 105.4(4) . . . yes
H4 O5 H5 106.5(4) . . . yes

#----------------------------------------------------------------------------#
#                   TONTO INSTRUCTION FILE                                   #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   TONTO REFLECTION FILE                                    #
#----------------------------------------------------------------------------#

# END of CIF
####################################################################### 
# 
# 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_4AP_HAR_neutron
_database_code_depnum_ccdc_archive 'CCDC 1989500'
loop_
_audit_author_name
_audit_author_address
'Simon Grabowsky'
;University of Bern
Switzerland
;
_audit_update_record             
;
2020-03-10 deposited with the CCDC.	2020-06-15 downloaded from the CCDC.
;

_audit_creation_date             2019-04-25T11:21:27-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_common            '4-aminopyridinium hydrogen maleate'
_chemical_formula_moiety         'C4 H3 O4, C5 H7 N2'
_chemical_formula_sum            'C9 H10 N2 O4'
_chemical_formula_weight         210.191
_chemical_absolute_configuration syn

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'p 1 21 1'
_symmetry_space_group_name_Hall  'p 2yb'
_symmetry_Int_Tables_number      4
loop_
_symmetry_equiv_pos_as_xyz
'+x, +y, +z'
'-x, +y+1/2, -z'

_cell_length_a                   7.85280(10)
_cell_length_b                   5.54510(10)
_cell_length_c                   10.9223(2)
_cell_angle_alpha                90
_cell_angle_beta                 96.394(7)
_cell_angle_gamma                90
_cell_volume                     472.648(14)
_cell_formula_units_Z            2
_cell_measurement_temperature    16.5(10)
_cell_measurement_reflns_used    109774
_cell_measurement_theta_min      0.94
_cell_measurement_theta_max      30.4
_cell_measurement_wavelength     0.3542

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.11
_exptl_crystal_size_mid          0.09
_exptl_crystal_size_min          0.08
_exptl_crystal_density_diffrn    1.477
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             220

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.039
_exptl_absorpt_correction_type   none
_shelx_estimated_absorpt_T_min   0.996
_shelx_estimated_absorpt_T_max   0.997

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   SPring-8
_diffrn_ambient_temperature      16.5(10)
_diffrn_radiation_wavelength     0.3532
_diffrn_radiation_type           synchrotron
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'SPring-8 BL02B1 Curved Imaging Plate'
_diffrn_detector_area_resol_mean 10
_diffrn_orient_matrix_type       fs_process
_diffrn_orient_matrix_ub_11      -0.018979
_diffrn_orient_matrix_ub_12      -0.095374
_diffrn_orient_matrix_ub_13      -0.078031
_diffrn_orient_matrix_ub_21      -0.126383
_diffrn_orient_matrix_ub_22      0.003037
_diffrn_orient_matrix_ub_23      0.00491
_diffrn_orient_matrix_ub_31      -0.009321
_diffrn_orient_matrix_ub_32      0.153024
_diffrn_orient_matrix_ub_33      -0.048731
_diffrn_measurement_device       'quarter Χ-circle diffractometer'
_diffrn_measurement_device_type  IPDSC-Q
_diffrn_measurement_method       'phi or omega oscillation scans'
_diffrn_standards_number         0
_diffrn_standards_interval_time  .
_diffrn_standards_interval_count .
_diffrn_reflns_av_R_equivalents  0.0243
_diffrn_reflns_av_unetI/netI     0.0142
_diffrn_reflns_number            70399
_diffrn_reflns_limit_h_min       -17
_diffrn_reflns_limit_h_max       18
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_theta_min         0.935
_diffrn_reflns_theta_max         26.277
_diffrn_reflns_theta_full        12.27
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.973
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.973
_diffrn_reflns_point_group_measured_fraction_full 0.995
_diffrn_reflns_point_group_measured_fraction_max 0.944
_reflns_Friedel_fraction_full    0.992
_reflns_Friedel_fraction_max     0.911
_reflns_Friedel_coverage         0.84
_reflns_number_total             14565
_reflns_number_gt                13813
_reflns_threshold_expression     'F>0 & F/u(F)>4.0 & |F_calc|>10^-3'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'CrystalClear (Rigaku/MSC Inc., 2006)'
_computing_cell_refinement       'CrystalClear (Rigaku/MSC Inc., 2006)'
_computing_data_reduction        
'CrystalClear (Rigaku/MSC Inc., 2006), SORTAV (Blessing, 1995)'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2014)'
_computing_structure_refinement  
'Tonto 18.12.17 github v. 2b3dd9c (Capelli, 2014)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     dual
_atom_sites_solution_hydrogens   difmap

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
  .  Hirshfeld atom refinement:
     .  Uses aspherical atomic scattering factors
        obtained from Hirshfeld partitioning of a
        gaussian quantum chemical wavefunction.
     .  Hirshfeld weight functions obtained from
        spherically averaged unrestricted atomic
        densities.
  .  Wavefunction type : rhf using 8A SC cluster charges, 
  .  Gaussian basis set: def2-TZVP
  .  Refinement based on |F| with weight=1/sigma(|F|)
  .  Negative |F|^^2 were pruned from the data
  .  |F| < 4.0 sigma(|F|) were pruned from the data
  .  Eigenvalues < 0.1E-04 removed from normal equations
  .  Reflection used in the refinement appear below
  .  Refined using the Tonto program
  . If constraints were applied they are defined by zero
  eigenvalues of the least-squares hessian, see the
  value of _refine_ls_SVD_threshold
;
_refine_ls_structure_factor_coef F
_refine_ls_coordinate_system     cartesian
_refine_ls_SVD_threshold         0.1E-02
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      sigma
_refine_ls_weighting_details     w=1/σ(F)
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_extinction_method     none
_refine_ls_number_reflns         13813
_refine_ls_number_parameters     165
_refine_ls_number_restraints     0
_refine_ls_number_constraints    61
_refine_ls_R_factor_all          0.0195
_refine_ls_R_factor_gt           0.0195
_refine_ls_wR_factor_gt          0.0171
_refine_ls_wR_factor_all         0.0171
_refine_ls_goodness_of_fit_gt    2.5401
_refine_ls_goodness_of_fit_all   2.5401
_refine_ls_shift/su_max          0.0067
_refine_ls_abs_structure_details 
;
 Flack x determined using 6079 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.0(4)
_refine_diff_density_max         0.3191
_refine_diff_density_min         -0.2819
_refine_diff_density_rms         0.0439

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0 0 'Hirshfeld partitioning of a quantum chemical wavefunction.'
H H 0 0 'Hirshfeld partitioning of a quantum chemical wavefunction.'
N N 0 0 'Hirshfeld partitioning of a quantum chemical wavefunction.'
O O 0 0 'Hirshfeld partitioning of a quantum chemical wavefunction.'

loop_
_atom_site_label
_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_disorder_group
O3 0.379877(17) 0.48351(13) 0.620710(12) 0.01022(4) Uani 1 0
O2 0.166278(19) -0.08686(13) 0.826656(11) 0.01093(4) Uani 1 0
O1 0.322273(18) 0.27723(13) 0.785854(11) 0.00972(4) Uani 1 0
O4 -0.000554(18) -0.35735(13) 0.720350(13) 0.01150(5) Uani 1 0
N2 0.579894(19) 0.81554(13) 0.754435(13) 0.00968(5) Uani 1 0
N1 0.88519(2) 1.35854(13) 0.916007(13) 0.00995(5) Uani 1 0
C1 0.31226(2) 0.30925(13) 0.668437(13) 0.00767(5) Uani 1 0
C5 0.78561(2) 1.18208(13) 0.863973(13) 0.00729(5) Uani 1 0
C6 0.74942(2) 1.16539(13) 0.733572(13) 0.00841(5) Uani 1 0
C4 0.09592(2) -0.18059(13) 0.724704(14) 0.00838(5) Uani 1 0
C2 0.21870(2) 0.13130(13) 0.581878(14) 0.00869(5) Uani 1 0
C8 0.61160(2) 0.82591(13) 0.878885(15) 0.00985(5) Uani 1 0
C3 0.13148(2) -0.07017(13) 0.604695(14) 0.00908(5) Uani 1 0
C9 0.71205(2) 1.00445(13) 0.936376(14) 0.00874(5) Uani 1 0
C7 0.64682(2) 0.98303(13) 0.682844(14) 0.00909(5) Uani 1 0
H1 0.2490(8) 0.0969(15) 0.8095(5) 0.01964977 Uani 1 0
H2 0.2250(6) 0.1778(8) 0.4837(4) 0.02354849 Uani 1 0
H6 0.8014(5) 1.2960(9) 0.6748(4) 0.02174089 Uani 1 0
H10 0.7343(6) 1.0085(8) 1.0376(4) 0.02232845 Uani 1 0
H3 0.0746(6) -0.1710(9) 0.5251(4) 0.0227843 Uani 1 0
H7 0.6137(5) 0.9629(8) 0.5825(3) 0.0202007 Uani 1 0
H9 0.5508(6) 0.6866(8) 0.9305(4) 0.02309 Uani 1 0
H4 0.9378(7) 1.4790(9) 0.8608(4) 0.0206427 Uani 1 0
H8 0.5021(6) 0.6771(9) 0.7113(5) 0.0189082 Uani 1 0
H5 0.8981(6) 1.3816(9) 1.0100(4) 0.0223951 Uani 1 0



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O3 C1 1.2446(2) . . yes
O2 C4 1.2955(2) . . yes
O1 C1 1.28839(19) . . yes
O4 C4 1.2365(2) . . yes
O2 H1 1.234(9) . . yes
O1 H1 1.196(9) . . yes
N2 C8 1.3556(2) . . yes
N2 C7 1.3571(2) . . yes
N1 C5 1.3390(2) . . yes
N2 H8 1.058(5) . . yes
N1 H4 1.018(4) . . yes
N1 H5 1.028(4) . . yes
C1 C2 1.5008(2) . . yes
C5 C6 1.4240(2) . . yes
C5 C9 1.4251(2) . . yes
C6 C7 1.3708(2) . . yes
C4 C3 1.5008(2) . . yes
C2 C3 1.3481(2) . . yes
C8 C9 1.3734(2) . . yes
C6 H6 1.077(4) . . yes
C2 H2 1.109(4) . . yes
C8 H9 1.097(4) . . yes
C3 H3 1.087(4) . . yes
C9 H10 1.100(4) . . yes
C7 H7 1.104(4) . . yes

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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O3 C1 O1 122.838(15) . . . yes
O2 C4 O4 123.496(15) . . . yes
O3 C1 C2 116.638(13) . . . yes
O2 C4 C3 118.949(15) . . . yes
O1 C1 C2 120.516(14) . . . yes
O4 C4 C3 117.554(14) . . . yes
O2 H1 O1 175.7(5) . . . yes
N2 C8 C9 121.403(15) . . . yes
N2 C7 C6 121.320(14) . . . yes
N1 C5 C6 120.938(14) . . . yes
N1 C5 C9 121.545(13) . . . yes
N2 C8 H9 116.4(2) . . . yes
N2 C7 H7 116.1(2) . . . yes
C1 O1 H1 110.7(3) . . . yes
C4 O2 H1 112.5(3) . . . yes
C8 N2 C7 120.600(15) . . . yes
C5 N1 H4 119.0(3) . . . yes
C5 N1 H5 120.2(3) . . . yes
C8 N2 H8 120.6(3) . . . yes
C7 N2 H8 118.8(3) . . . yes
C1 C2 C3 130.658(14) . . . yes
C5 C6 C7 119.674(14) . . . yes
C5 C9 C8 119.482(14) . . . yes
C6 C5 C9 117.517(14) . . . yes
C4 C3 C2 130.339(15) . . . yes
C1 C2 H2 112.6(2) . . . yes
C5 C6 H6 120.3(2) . . . yes
C5 C9 H10 121.0(2) . . . yes
C6 C7 H7 122.6(2) . . . yes
C4 C3 H3 112.9(2) . . . yes
C2 C3 H3 116.8(2) . . . yes
C8 C9 H10 119.5(2) . . . yes
C3 C2 H2 116.7(2) . . . yes
C9 C8 H9 122.2(2) . . . yes
C7 C6 H6 120.0(2) . . . yes
H4 N1 H5 120.6(4) . . . yes

#----------------------------------------------------------------------------#
#                   TONTO INSTRUCTION FILE                                   #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   TONTO REFLECTION FILE                                    #
#----------------------------------------------------------------------------#

# END of CIF
####################################################################### 
# 
# 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_PhAla_HAR_neutron
_database_code_depnum_ccdc_archive 'CCDC 1989535'
loop_
_audit_author_name
_audit_author_address
'Simon Grabowsky'
;University of Bern
Switzerland
;
_audit_update_record             
;
2020-03-10 deposited with the CCDC.	2020-06-15 downloaded from the CCDC.
;

_audit_creation_date             2019-05-02T17:25:29-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_common            'L-phenylalaninium hydrogen maleate'
_chemical_formula_moiety         'C4 H3 O4, C9 H12 N O2'
_chemical_formula_sum            'C13 H15 N O6'
_chemical_formula_weight         281.2676
_chemical_absolute_configuration syn

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'p 1 21 1'
_symmetry_space_group_name_Hall  'p 2yb'
_symmetry_Int_Tables_number      4
loop_
_symmetry_equiv_pos_as_xyz
'+x, +y, +z'
'-x, +y+1/2, -z'

_cell_length_a                   10.905(2)
_cell_length_b                   5.2338(10)
_cell_length_c                   11.439(2)
_cell_angle_alpha                90
_cell_angle_beta                 101.36(3)
_cell_angle_gamma                90
_cell_volume                     640.1(2)
_cell_formula_units_Z            2
_cell_measurement_temperature    25
_cell_measurement_reflns_used    124185
_cell_measurement_theta_min      0.9
_cell_measurement_theta_max      26.3

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.03
_exptl_crystal_density_diffrn    1.459
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             296

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.039
_exptl_absorpt_correction_type   none

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   SPring-8
_diffrn_ambient_temperature      25
_diffrn_radiation_wavelength     0.354
_diffrn_radiation_type           synchrotron
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'SPring-8 BL02B1 Curved Imaging Plate'
_diffrn_measurement_device       'quarter Χ-circle diffractometer'
_diffrn_measurement_device_type  IPDSC-Q
_diffrn_measurement_method       'phi or omega oscillation scans'
_diffrn_reflns_av_R_equivalents  0.022
_diffrn_reflns_av_unetI/netI     0.063
_diffrn_reflns_number            124185
_diffrn_reflns_limit_h_min       -24
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_limit_l_max       25
_diffrn_reflns_theta_min         0.9
_diffrn_reflns_theta_max         23.16
_diffrn_reflns_theta_full        23.16
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_reflns_number_total             7820
_reflns_number_gt                7564
_reflns_threshold_expression     'F>0 & F/u(F)>4.0 & |F_calc|>10^-3'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   HAR

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
  .  Hirshfeld atom refinement:
     .  Uses aspherical atomic scattering factors
        obtained from Hirshfeld partitioning of a
        gaussian quantum chemical wavefunction.
     .  Hirshfeld weight functions obtained from
        spherically averaged unrestricted atomic
        densities.
  .  Wavefunction type : rhf using 8A SC cluster charges, 
  .  Gaussian basis set: def2-TZVP
  .  Refinement based on |F| with weight=1/sigma(|F|)
  .  Negative |F|^^2 were pruned from the data
  .  |F| < 4.0 sigma(|F|) were pruned from the data
  .  Eigenvalues < 0.1E-04 removed from normal equations
  .  Reflection used in the refinement appear below
  .  Refined using the Tonto program
  . If constraints were applied they are defined by zero
  eigenvalues of the least-squares hessian, see the
  value of _refine_ls_SVD_threshold
;
_refine_ls_structure_factor_coef F
_refine_ls_coordinate_system     cartesian
_refine_ls_SVD_threshold         0.1E-02
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      sigma
_refine_ls_weighting_details     w=1/σ(F)
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_extinction_method     none
_refine_ls_number_reflns         7564
_refine_ls_number_parameters     225
_refine_ls_number_restraints     0
_refine_ls_number_constraints    91
_refine_ls_R_factor_all          0.0204
_refine_ls_R_factor_gt           0.0204
_refine_ls_wR_factor_gt          0.0213
_refine_ls_wR_factor_all         0.0213
_refine_ls_goodness_of_fit_gt    0.8688
_refine_ls_goodness_of_fit_all   0.8688
_refine_ls_shift/su_max          0.0018
_refine_ls_shift/su_mean         0
_refine_ls_abs_structure_details 'Flack H D (1983), Acta Cryst. A39, 876-881'
_refine_ls_abs_structure_Flack   0.3(3)
_refine_diff_density_max         0.2128
_refine_diff_density_min         -0.2321
_refine_diff_density_rms         0.0355

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0 0 'Hirshfeld partitioning of a quantum chemical wavefunction.'
H H 0 0 'Hirshfeld partitioning of a quantum chemical wavefunction.'
N N 0 0 'Hirshfeld partitioning of a quantum chemical wavefunction.'
O O 0 0 'Hirshfeld partitioning of a quantum chemical wavefunction.'

loop_
_atom_site_label
_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_disorder_group
O1 0.09519(2) 0.4789(2) -0.380786(19) 0.01191(7) Uani 1 0
O2 0.12318(2) 0.5098(3) -0.58414(2) 0.01268(7) Uani 1 0
O3 0.13523(2) 0.7087(3) -0.216558(18) 0.01135(7) Uani 1 0
O4 0.17831(2) 0.8006(3) -0.703287(19) 0.01256(7) Uani 1 0
C1 0.13463(2) 0.6827(3) -0.32530(2) 0.00904(8) Uani 1 0
C2 0.18017(2) 0.9015(3) -0.38885(2) 0.01035(8) Uani 1 0
C3 0.18958(2) 0.9240(3) -0.50384(2) 0.01072(8) Uani 1 0
C4 0.16124(2) 0.7359(3) -0.60350(2) 0.00981(8) Uani 1 0
H1 0.1078(12) 0.489(3) -0.4822(15) 0.01998334 Uani 1 0
H2 0.2046(9) 1.0690(17) -0.3345(7) 0.02180597 Uani 1 0
H3 0.2249(9) 1.1057(18) -0.5315(8) 0.02201039 Uani 1 0
O5 0.22349(2) 1.0888(3) -0.092741(19) 0.01194(7) Uani 1 0
O6 0.095148(18) 0.9228(3) 0.017761(18) 0.00959(6) Uani 1 0
N1 0.12387(2) 1.2986(3) 0.17419(2) 0.01045(7) Uani 1 0
C5 0.16349(2) 1.0925(3) -0.00447(2) 0.00796(7) Uani 1 0
C6 0.18068(2) 1.3376(3) 0.06747(2) 0.00850(7) Uani 1 0
C7 0.31498(2) 1.4373(3) 0.10138(2) 0.00954(8) Uani 1 0
C8 0.40365(2) 1.2630(3) 0.18246(2) 0.00885(7) Uani 1 0
C9 0.41966(2) 1.2880(3) 0.30620(2) 0.01157(8) Uani 1 0
C10 0.49986(3) 1.1256(3) 0.38179(2) 0.01323(9) Uani 1 0
C11 0.56581(2) 0.9371(3) 0.33444(3) 0.01262(9) Uani 1 0
C12 0.55177(2) 0.9119(3) 0.21137(3) 0.01280(9) Uani 1 0
C13 0.47072(2) 1.0738(3) 0.13592(2) 0.01124(8) Uani 1 0
H41 0.1357(9) 1.463(2) 0.2262(9) 0.0206249 Uani 1 0
H42 0.1603(10) 1.144(2) 0.2214(9) 0.02138947 Uani 1 0
H43 0.0279(8) 1.258(2) 0.1504(9) 0.0199827 Uani 1 0
H5 0.1915(11) 0.932(3) -0.1475(11) 0.0184767 Uani 1 0
H6 0.1227(7) 1.4831(17) 0.0122(7) 0.0158157 Uani 1 0
H71 0.3117(8) 1.6239(17) 0.1431(8) 0.0199048 Uani 1 0
H72 0.3468(8) 1.469(2) 0.0173(7) 0.0192018 Uani 1 0
H9 0.3695(8) 1.445(2) 0.3387(7) 0.0224996 Uani 1 0
H10 0.5125(9) 1.148(2) 0.4817(7) 0.0255127 Uani 1 0
H11 0.6285(9) 0.809(2) 0.3957(8) 0.0250307 Uani 1 0
H12 0.6056(10) 0.764(2) 0.1704(8) 0.0241842 Uani 1 0
H13 0.4599(8) 1.052(2) 0.0385(7) 0.0217391 Uani 1 0



#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.2719(3) . . yes
O2 C4 1.2877(3) . . yes
O3 C1 1.2500(3) . . yes
O4 C4 1.2393(3) . . yes
O5 C5 1.3070(3) . . yes
O6 C5 1.2179(3) . . yes
O1 H1 1.196(18) . . yes
O2 H1 1.215(18) . . yes
O5 H5 1.050(14) . . yes
N1 C6 1.4879(3) . . yes
N1 H41 1.038(10) . . yes
N1 H42 1.010(10) . . yes
N1 H43 1.050(8) . . yes
C1 C2 1.4930(4) . . yes
C2 C3 1.3445(3) . . yes
C3 C4 1.4919(4) . . yes
C5 C6 1.5156(3) . . yes
C6 C7 1.5310(3) . . yes
C7 C8 1.5081(3) . . yes
C8 C9 1.3978(3) . . yes
C8 C13 1.3971(3) . . yes
C9 C10 1.3919(4) . . yes
C10 C11 1.3918(4) . . yes
C11 C12 1.3921(4) . . yes
C12 C13 1.3943(4) . . yes
C2 H2 1.078(8) . . yes
C3 H3 1.095(9) . . yes
C6 H6 1.105(8) . . yes
C7 H71 1.091(9) . . yes
C7 H72 1.098(8) . . yes
C9 H9 1.091(9) . . yes
C10 H10 1.130(8) . . yes
C11 H11 1.104(9) . . yes
C12 H12 1.129(9) . . yes
C13 H13 1.103(8) . . yes

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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 O3 121.53(2) . . . yes
O2 C4 O4 121.43(2) . . . yes
O5 C5 O6 124.79(2) . . . yes
O1 C1 C2 120.82(2) . . . yes
O2 C4 C3 120.02(2) . . . yes
O3 C1 C2 117.64(2) . . . yes
O4 C4 C3 118.52(2) . . . yes
O5 C5 C6 113.88(2) . . . yes
O6 C5 C6 121.27(2) . . . yes
O1 H1 O2 177.1(14) . . . yes
N1 C6 C5 107.60(2) . . . yes
N1 C6 C7 111.781(19) . . . yes
N1 C6 H6 106.3(4) . . . yes
C1 O1 H1 110.8(7) . . . yes
C4 O2 H1 110.9(7) . . . yes
C5 O5 H5 108.3(6) . . . yes
C6 N1 H41 109.4(6) . . . yes
C6 N1 H42 111.4(6) . . . yes
C6 N1 H43 111.7(5) . . . yes
C1 C2 C3 129.83(2) . . . yes
C2 C3 C4 130.20(2) . . . yes
C5 C6 C7 115.843(19) . . . yes
C6 C7 C8 114.52(2) . . . yes
C7 C8 C9 120.20(2) . . . yes
C7 C8 C13 120.98(2) . . . yes
C8 C9 C10 120.64(2) . . . yes
C8 C13 C12 120.70(2) . . . yes
C9 C8 C13 118.82(2) . . . yes
C9 C10 C11 120.05(2) . . . yes
C10 C11 C12 119.91(2) . . . yes
C11 C12 C13 119.88(2) . . . yes
C1 C2 H2 114.3(5) . . . yes
C2 C3 H3 117.2(5) . . . yes
C3 C2 H2 115.8(5) . . . yes
C4 C3 H3 112.6(5) . . . yes
C5 C6 H6 106.1(5) . . . yes
C6 C7 H71 107.7(5) . . . yes
C6 C7 H72 106.4(4) . . . yes
C7 C6 H6 108.7(4) . . . yes
C8 C7 H71 110.2(5) . . . yes
C8 C7 H72 110.8(5) . . . yes
C8 C9 H9 116.4(4) . . . yes
C8 C13 H13 119.9(5) . . . yes
C9 C10 H10 120.0(5) . . . yes
C10 C9 H9 122.9(4) . . . yes
C10 C11 H11 119.1(5) . . . yes
C11 C10 H10 119.9(5) . . . yes
C11 C12 H12 121.5(5) . . . yes
C12 C11 H11 121.0(5) . . . yes
C12 C13 H13 119.4(5) . . . yes
C13 C12 H12 118.6(5) . . . yes
H41 N1 H42 111.4(8) . . . yes
H41 N1 H43 108.8(8) . . . yes
H42 N1 H43 104.0(9) . . . yes
H71 C7 H72 106.9(7) . . . yes

#----------------------------------------------------------------------------#
#                   TONTO INSTRUCTION FILE                                   #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   TONTO REFLECTION FILE                                    #
#----------------------------------------------------------------------------#

# END of CIF
####################################################################### 
# 
# 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_Mg_HAR_neutron
_database_code_depnum_ccdc_archive 'CCDC 1989534'
loop_
_audit_author_name
_audit_author_address
'Simon Grabowsky'
;University of Bern
Switzerland
;
_audit_update_record             
;
2020-03-10 deposited with the CCDC.	2020-06-15 downloaded from the CCDC.
;

_audit_creation_date             2019-04-30T15:35:05-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'

#----------------------------------------------------------------------------#
#                   CHEMICAL INFORMATION                                     #
#----------------------------------------------------------------------------#

_chemical_name_common            'Magnesium bis(hydrogen maleate) hexahydrate'
_chemical_formula_moiety         '2(C4 H3 O4), Mg, 6(H2 O)'
_chemical_formula_sum            'C8 H18 Mg O14'
_chemical_formula_weight         362.5363
_chemical_absolute_configuration syn

#----------------------------------------------------------------------------#
#                   UNIT CELL INFORMATION                                    #
#----------------------------------------------------------------------------#

_symmetry_cell_setting           Monoclinic
_symmetry_space_group_name_H-M   'p 1 21/c 1'
_symmetry_space_group_name_Hall  '-p 2ybc'
_symmetry_Int_Tables_number      14
loop_
_symmetry_equiv_pos_as_xyz
'+x, +y, +z'
'-x, -y, -z'
'-x, +y+1/2, -z+1/2'
'+x, -y+1/2, +z+1/2'

_cell_length_a                   10.195(2)
_cell_length_b                   11.759(2)
_cell_length_c                   6.6206(13)
_cell_angle_alpha                90
_cell_angle_beta                 103.67(3)
_cell_angle_gamma                90
_cell_volume                     771.2(3)
_cell_formula_units_Z            2
_cell_measurement_temperature    14.9(2)
_cell_measurement_reflns_used    256398
_cell_measurement_theta_min      0.86
_cell_measurement_theta_max      36.06
_cell_measurement_wavelength     0.3532

#----------------------------------------------------------------------------#
#                   CRYSTAL INFORMATION                                      #
#----------------------------------------------------------------------------#

_exptl_crystal_description       block
_exptl_crystal_colour            colorless
_exptl_crystal_size_max          0.15
_exptl_crystal_size_mid          0.13
_exptl_crystal_size_min          0.1
_exptl_crystal_density_diffrn    1.561
_exptl_crystal_density_method    'not measured'
_exptl_crystal_F_000             380

#----------------------------------------------------------------------------#
#                   ABSORPTION CORRECTION                                    #
#----------------------------------------------------------------------------#

_exptl_absorpt_coefficient_mu    0.049
_exptl_absorpt_correction_type   none

#----------------------------------------------------------------------------#
#                   DATA COLLECTION                                          #
#----------------------------------------------------------------------------#

_diffrn_source                   SPring-8
_diffrn_ambient_temperature      14.9(2)
_diffrn_radiation_wavelength     0.3532
_diffrn_radiation_type           synchrotron
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_detector                 'SPring-8 BL02B1 Curved Imaging Plate'
_diffrn_detector_area_resol_mean 10
_diffrn_orient_matrix_type       fs_process
_diffrn_orient_matrix_ub_11      -0.103165
_diffrn_orient_matrix_ub_12      0.06297
_diffrn_orient_matrix_ub_13      -0.00545
_diffrn_orient_matrix_ub_21      0.007052
_diffrn_orient_matrix_ub_22      -0.008616
_diffrn_orient_matrix_ub_23      0.098566
_diffrn_orient_matrix_ub_31      0.116059
_diffrn_orient_matrix_ub_32      0.056498
_diffrn_orient_matrix_ub_33      0.021106
_diffrn_measurement_device       'quarter Χ-circle diffractometer'
_diffrn_measurement_device_type  IPDSC-Q
_diffrn_measurement_method       'phi or omega oscillation scans'
_diffrn_standards_number         0
_diffrn_reflns_av_R_equivalents  0.0265
_diffrn_reflns_av_unetI/netI     0.0088
_diffrn_reflns_number            155955
_diffrn_reflns_limit_h_min       -25
_diffrn_reflns_limit_h_max       23
_diffrn_reflns_limit_k_min       -29
_diffrn_reflns_limit_k_max       29
_diffrn_reflns_limit_l_min       -16
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         1.021
_diffrn_reflns_theta_max         26.199
_diffrn_reflns_theta_full        12.235
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.997
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.997
_reflns_Friedel_coverage         0
_reflns_number_total             12589
_reflns_number_gt                11643
_reflns_threshold_expression     'F>0 & F/u(F)>4.0 & |F_calc|>10^-3'

#----------------------------------------------------------------------------#
#                   COMPUTER PROGRAMS USED                                   #
#----------------------------------------------------------------------------#

_computing_data_collection       'CrystalClear (Rigaku/MSC Inc., 2006)'
_computing_cell_refinement       'CrystalClear (Rigaku/MSC Inc., 2006)'
_computing_data_reduction        
'CrystalClear (Rigaku/MSC Inc., 2006), SORTAV (Blessing, 1995)'
_computing_structure_solution    'SHELXT-2014 (Sheldrick, 2014)'
_computing_structure_refinement  
'Tonto 18.12.17 github v. 2b3dd9c (Capelli, 2014)'

#----------------------------------------------------------------------------#
#                   STRUCTURE SOLUTION                                       #
#----------------------------------------------------------------------------#

_atom_sites_solution_primary     dual
_atom_sites_solution_hydrogens   difmap

#----------------------------------------------------------------------------#
#                   REFINEMENT INFORMATION                                   #
#----------------------------------------------------------------------------#

_refine_special_details          
;
  .  Hirshfeld atom refinement:
     .  Uses aspherical atomic scattering factors
        obtained from Hirshfeld partitioning of a
        gaussian quantum chemical wavefunction.
     .  Hirshfeld weight functions obtained from
        spherically averaged unrestricted atomic
        densities.
  .  Wavefunction type : rhf using 8A SC cluster charges, 
  .  Gaussian basis set: def2-TZVP
  .  Refinement based on |F| with weight=1/sigma(|F|)
  .  Negative |F|^^2 were pruned from the data
  .  |F| < 4.0 sigma(|F|) were pruned from the data
  .  Eigenvalues < 0.1E-04 removed from normal equations
  .  Reflection used in the refinement appear below
  .  Refined using the Tonto program
  . If constraints were applied they are defined by zero
  eigenvalues of the least-squares hessian, see the
  value of _refine_ls_SVD_threshold
;
_refine_ls_structure_factor_coef F
_refine_ls_coordinate_system     cartesian
_refine_ls_SVD_threshold         0.1E-02
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      sigma
_refine_ls_weighting_details     w=1/σ(F)
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_extinction_method     none
_refine_ls_number_reflns         11643
_refine_ls_number_parameters     133
_refine_ls_number_restraints     0
_refine_ls_number_constraints    57
_refine_ls_R_factor_all          0.0159
_refine_ls_R_factor_gt           0.0159
_refine_ls_wR_factor_gt          0.0168
_refine_ls_wR_factor_all         0.0168
_refine_ls_goodness_of_fit_gt    3.0663
_refine_ls_goodness_of_fit_all   3.0663
_refine_ls_shift/su_max          0.0091
_refine_ls_shift/su_mean         0
_refine_diff_density_max         0.4107
_refine_diff_density_min         -0.3124
_refine_diff_density_rms         0.0263

#----------------------------------------------------------------------------#
#                   CONSTRAINTS AND RESTRAINTS                               #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   ATOMIC TYPES, COORDINATES AND THERMAL PARAMETERS         #
#----------------------------------------------------------------------------#

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0 0 'Hirshfeld partitioning of a quantum chemical wavefunction.'
H H 0 0 'Hirshfeld partitioning of a quantum chemical wavefunction.'
O O 0 0 'Hirshfeld partitioning of a quantum chemical wavefunction.'
Mg Mg 0 0 'Hirshfeld partitioning of a quantum chemical wavefunction.'

loop_
_atom_site_label
_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_disorder_group
O1 0.097264(8) 0.091897(6) 0.872538(13) 0.00799(2) Uani 1 0
O3 0.292767(8) 0.179951(6) 0.918652(13) 0.00829(2) Uani 1 0
O2 -0.138419(8) 0.140646(6) 0.783355(14) 0.00894(2) Uani 1 0
O4 -0.264810(8) 0.295341(6) 0.717000(14) 0.00881(2) Uani 1 0
C1 0.167190(9) 0.183288(7) 0.887272(14) 0.00596(2) Uani 1 0
C2 0.101227(10) 0.297789(7) 0.869478(15) 0.00679(3) Uani 1 0
C4 -0.152899(9) 0.249357(7) 0.771169(14) 0.00622(2) Uani 1 0
C3 -0.030949(10) 0.324924(7) 0.822541(15) 0.00698(3) Uani 1 0
O5 0.490436(8) -0.173475(6) 0.486923(14) 0.00921(2) Uani 1 0
O6 0.350541(9) -0.000322(7) 0.665286(15) 0.01023(3) Uani 1 0
O7 0.350321(10) 0.007796(7) 0.229923(14) 0.01194(3) Uani 1 0
Mg1 0.5 0 0.5 0.005287(17) Uani 1 0
H1 -0.0197(4) 0.1113(3) 0.8321(7) 0.01882229 Uani 1 0
H3 -0.0582(3) 0.4136(2) 0.8169(5) 0.0217345 Uani 1 0
H2 0.1735(3) 0.3677(2) 0.8956(5) 0.02107729 Uani 1 0
H4 0.4138(3) -0.2176(3) 0.4114(7) 0.0220935 Uani 1 0
H5 0.5670(3) -0.2223(3) 0.5252(6) 0.0227268 Uani 1 0
H7 0.3164(4) -0.0692(3) 0.7130(6) 0.0215466 Uani 1 0
H6 0.3385(4) 0.0607(3) 0.7578(6) 0.0228036 Uani 1 0
H8 0.3398(4) 0.0606(3) 0.1177(6) 0.0240812 Uani 1 0
H9 0.2746(4) -0.0413(3) 0.2055(6) 0.0232912 Uani 1 0

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 0.00518(2) 0.005451(18) 0.01326(3) 0.000082(17) 0.002002(18) -0.000292(15)
O3 0.00456(2) 0.00711(2) 0.01307(3) 0.000151(18) 0.001850(18) -0.000309(16)
O2 0.00506(2) 0.006006(18) 0.01554(3) -0.000006(19) 0.001998(19) -0.000490(16)
O4 0.00505(2) 0.00782(2) 0.01314(3) -0.000830(18) 0.001330(18) 0.000901(16)
C1 0.00442(3) 0.00562(2) 0.00783(3) 0.000079(19) 0.001458(19) -0.000158(18)
C2 0.00519(3) 0.00548(2) 0.00963(3) -0.00003(2) 0.00160(2) -0.000310(18)
C4 0.00453(2) 0.00621(2) 0.00801(3) -0.000281(19) 0.001668(19) 0.000153(18)
C3 0.00534(3) 0.00545(2) 0.01006(3) -0.00006(2) 0.00166(2) 0.000013(19)
O5 0.00661(2) 0.005686(19) 0.01477(3) -0.000252(18) 0.00142(2) 0.000288(16)
O6 0.01072(3) 0.00850(2) 0.01391(3) -0.00159(2) 0.00778(2) -0.001638(18)
O7 0.00976(3) 0.01215(3) 0.01134(3) 0.00424(2) -0.00267(2) -0.00405(2)
Mg1 0.004147(17) 0.004964(15) 0.006871(17) 0.000378(12) 0.001544(13)
0.000134(12)
H1 0.02 0.0139 0.0226 -0.0007 0.0051 -0.0034
H3 0.0179 0.01 0.0363 -0.0003 0.0044 0.002
H2 0.0152 0.0125 0.0344 -0.0011 0.0036 -0.006
H4 0.0161 0.0176 0.0292 -0.0043 -0.0014 -0.0039
H5 0.0169 0.0171 0.0318 0.0003 0.001 0.0055
H7 0.0249 0.0156 0.0266 0.003 0.011 -0.0041
H6 0.0298 0.0179 0.0229 -0.0069 0.0106 -0.0005
H8 0.0274 0.0241 0.019 0.0099 0.002 -0.0015
H9 0.0177 0.0223 0.0275 0.0013 0.0006 -0.0099


#----------------------------------------------------------------------------#
#                   MOLECULAR GEOMETRY                                       #
#----------------------------------------------------------------------------#

_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_1
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
Mg1 O5 2.04308(7) . . yes
Mg1 O6 2.07543(9) . . yes
Mg1 O7 2.06023(8) . . yes
O1 C1 1.28054(11) . . yes
O3 C1 1.24822(12) . . yes
O2 C4 1.28717(11) . . yes
O4 C4 1.23666(11) . . yes
O1 H1 1.181(5) . . yes
O2 H1 1.227(5) . . yes
O5 H4 0.972(3) . . yes
O5 H5 0.953(3) . . yes
O6 H7 0.964(3) . . yes
O6 H6 0.970(4) . . yes
O7 H8 0.955(3) . . yes
O7 H9 0.947(3) . . yes
C1 C2 1.49717(12) . . yes
C2 C3 1.34770(13) . . yes
C4 C3 1.50038(13) . . yes
C2 H2 1.090(3) . . yes
C3 H3 1.077(3) . . yes

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_2
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
Mg1 O5 H4 125.4(2) . . . yes
Mg1 O5 H5 124.2(2) . . . yes
Mg1 O6 H7 122.8(2) . . . yes
Mg1 O6 H6 123.4(2) . . . yes
Mg1 O7 H8 128.9(2) . . . yes
Mg1 O7 H9 121.9(2) . . . yes
O5 Mg1 O6 89.249(3) . . . yes
O5 Mg1 O7 89.399(3) . . . yes
O6 Mg1 O7 88.406(4) . . . yes
O1 C1 O3 121.127(8) . . . yes
O2 C4 O4 122.459(8) . . . yes
O1 C1 C2 121.139(8) . . . yes
O3 C1 C2 117.732(8) . . . yes
O2 C4 C3 119.825(8) . . . yes
O4 C4 C3 117.714(8) . . . yes
O1 H1 O2 174.3(4) . . . yes
C1 O1 H1 111.67(19) . . . yes
C4 O2 H1 112.79(18) . . . yes
C1 C2 C3 129.576(8) . . . yes
C2 C3 C4 129.931(8) . . . yes
C1 C2 H2 113.05(15) . . . yes
C2 C3 H3 118.19(14) . . . yes
C4 C3 H3 111.87(14) . . . yes
C3 C2 H2 117.35(15) . . . yes
H4 O5 H5 108.9(3) . . . yes
H7 O6 H6 107.7(4) . . . yes
H8 O7 H9 109.1(3) . . . yes

#----------------------------------------------------------------------------#
#                   TONTO INSTRUCTION FILE                                   #
#----------------------------------------------------------------------------#


#----------------------------------------------------------------------------#
#                   TONTO REFLECTION FILE                                    #
#----------------------------------------------------------------------------#

# END of CIF
