# 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_1mm
_database_code_depnum_ccdc_archive 'CCDC 2020635'
_audit_update_record             
;
2020-07-31 deposited with the CCDC.	2020-12-07 downloaded from the CCDC.
;

_audit_creation_date             '26-May-05 T12:21:25-00:00'
_audit_creation_method           'XD routine XDCIF'
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.3
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic

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

_chemical_name_systematic        'RR-tartaric acid'

_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C4 H6 O6'
_chemical_formula_sum            'C4 H6 O6'
_chemical_formula_weight         150.09

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
_cell_length_a                   6.1757(2)
_cell_length_b                   5.9211(2)
_cell_length_c                   7.7084(3)
_cell_angle_alpha                90
_cell_angle_beta                 100.434(2)
_cell_angle_gamma                90
_cell_volume                     277.212(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6532
_cell_measurement_theta_min      2.7
_cell_measurement_theta_max      53.6

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.798
_exptl_crystal_F_000             156
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.177
_shelx_estimated_absorpt_T_min   0.949
_shelx_estimated_absorpt_T_max   0.966
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9569
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX CCD area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14423
_diffrn_reflns_av_unetI/netI     0.0335
_diffrn_reflns_av_R_equivalents  0.0281
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.687
_diffrn_reflns_theta_max         54.520
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.878
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             6147
_reflns_number_gt                5787
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.702
_reflns_Friedel_fraction_max     0.767
_reflns_Friedel_fraction_full    1.000
_reflns_special_details          
;
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;

_computing_data_collection       'SMART (Bruker, 2001)'
_computing_cell_refinement       'SMART (Bruker, 2001)'
_computing_data_reduction        'SAINT-Plus (Bruker, 2009)'
_computing_structure_solution    'SHELXS '
_computing_structure_refinement  'Volkov et al, (2006)'
_computing_molecular_graphics    'Volkov et al, (2006)'
_computing_publication_material  'Volkov et al, (2006)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 2224 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(2)
_chemical_absolute_configuration rmad
_refine_ls_number_restraints     0
_refine_ls_R_factor_gt           0.025
_refine_ls_R_factor_all          0.029
_refine_ls_R_Fsqd_factor         0.037
_refine_ls_wR_factor_ref         0.048
_refine_ls_number_reflns         6147
_refine_ls_number_parameters     389
_refine_ls_goodness_of_fit_ref   1.023
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
;    calc w2 = q/[s²(Fo²) + (0.02 P)² + 0.00 P + 0.00 + 0.00 sin(th)]
     where P = (0.3333 Fo² + 0.6667 Fc²)
           q = 1.0
;
_refine_ls_shift/su_max          0.00003

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

loop_
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_occupancy
_atom_site_symmetry_multiplicity
O(1) 0.69728(4) 0.729543 0.39009(3) 0.011 1 2
O(2) 1.02409(4) 0.68810(6) 0.57097(3) 0.011 1 2
O(3) 0.48778(4) 0.75473(6) 0.66200(3) 0.011 1 2
O(4) 0.76545(4) 1.14449(6) 0.69278(3) 0.009 1 2
O(5) 0.65088(5) 1.13789(7) 1.02204(3) 0.014 1 2
O(6) 0.82049(4) 0.80257(7) 1.07914(3) 0.013 1 2
C(1) 0.80957(5) 0.71537(7) 0.53693(4) 0.008 1 2
C(2) 0.71711(4) 0.73675(7) 0.70582(4) 0.008 1 2
C(3) 0.81926(5) 0.95235(7) 0.80001(4) 0.008 1 2
C(4) 0.75106(5) 0.97790(7) 0.97897(4) 0.009 1 2
H(2) 1.0951(13) 0.6772(15) 0.4671(12) 0.023 1 2
H(3) 0.4287(10) 0.7254(16) 0.7694(10) 0.022 1 2
H(4) 0.6061(12) 1.1527(14) 0.6540(8) 0.019 1 2
H(6) 0.7644(13) 0.7999(16) 1.1911(11) 0.025 1 2
H(2A) 0.7692(15) 0.5913(17) 0.7880(11) 0.015 1 2
H(3A) 0.9975(15) 0.9391(17) 0.8257(11) 0.014 1 2


#----------------------------------------------------------------------------#
#                   MULTIPOLE PARAMETERS                                     #
#----------------------------------------------------------------------------#

loop_
_atom_rho_multipole_atom_label
_atom_rho_multipole_coeff_Pv
_atom_rho_multipole_coeff_P00
_atom_rho_multipole_coeff_P11
_atom_rho_multipole_coeff_P1-1
_atom_rho_multipole_coeff_P10
_atom_rho_multipole_coeff_P20
_atom_rho_multipole_coeff_P21
_atom_rho_multipole_coeff_P2-1
_atom_rho_multipole_coeff_P22
_atom_rho_multipole_coeff_P2-2
_atom_rho_multipole_coeff_P30
_atom_rho_multipole_coeff_P31
_atom_rho_multipole_coeff_P3-1
_atom_rho_multipole_coeff_P32
_atom_rho_multipole_coeff_P3-2
_atom_rho_multipole_coeff_P33
_atom_rho_multipole_coeff_P3-3
_atom_rho_multipole_coeff_P40
_atom_rho_multipole_coeff_P41
_atom_rho_multipole_coeff_P4-1
_atom_rho_multipole_coeff_P42
_atom_rho_multipole_coeff_P4-2
_atom_rho_multipole_coeff_P43
_atom_rho_multipole_coeff_P4-3
_atom_rho_multipole_coeff_P44
_atom_rho_multipole_coeff_P4-4
_atom_rho_multipole_kappa
_atom_rho_multipole_kappa_prime0
_atom_rho_multipole_kappa_prime1
_atom_rho_multipole_kappa_prime2
_atom_rho_multipole_kappa_prime3
_atom_rho_multipole_kappa_prime4
_atom_rho_multipole_radial_slater_n0
_atom_rho_multipole_radial_slater_zeta0
_atom_rho_multipole_radial_slater_n1
_atom_rho_multipole_radial_slater_zeta1
_atom_rho_multipole_radial_slater_n2
_atom_rho_multipole_radial_slater_zeta2
_atom_rho_multipole_radial_slater_n3
_atom_rho_multipole_radial_slater_zeta3
_atom_rho_multipole_radial_slater_n4
_atom_rho_multipole_radial_slater_zeta4
O(1) 6.18(5) 0 0.00(2) -0.004(14) -0.096(15) 0.003(13) 0.021(15) 0.059(12)
-0.071(12) -0.012(14) 0.072(12) -0.032(17) -0.002(10) -0.001(11) 0.052(17)
0.014(15) -0.020(11) 0.054(14) -0.031(15) -0.022(12) 0.003(13) 0.015(16)
-0.026(15) 0.025(13) -0.009(13) 0.002(14) 0.989(3) 0.96(3) 0.959365 0.959365
0.959365 0.959365 2 4.466 2 4.466 2 4.466 3 4.466 4 4.466
O(2) 6.20(5) 0 -0.01(2) -0.080(15) -0.043(16) -0.058(14) 0.016(14) 0.019(12)
0.009(13) -0.017(14) 0.055(13) -0.030(18) -0.008(11) 0.045(12) -0.037(18)
0.016(16) -0.001(12) 0.037(14) -0.009(15) 0.010(13) -0.028(14) 0.021(15)
-0.001(14) -0.002(14) -0.032(14) 0.015(13) 0.989(3) 0.96(3) 0.959365 0.959365
0.959365 0.959365 2 4.466 2 4.466 2 4.466 3 4.466 4 4.466
O(3) 6.51(5) 0 0.007(19) -0.075(11) -0.049(12) -0.060(13) 0.013(13) 0.049(11)
0.038(12) -0.010(13) 0.040(11) 0.000(13) -0.019(9) 0.031(10) -0.029(14)
-0.001(12) -0.035(10) 0.024(12) -0.001(12) 0.035(11) 0.009(11) 0.015(12)
0.007(11) 0.005(11) -0.011(11) 0.011(11) 0.978(3) 1.15(5) 1.145123 1.145123
1.145123 1.145123 2 4.466 2 4.466 2 4.466 3 4.466 4 4.466
O(4) 6.37(5) 0 -0.034(14) -0.101(18) -0.025(11) 0.014(11) 0.025(11) 0.059(11)
0.056(12) 0.047(10) 0.065(9) 0.012(10) 0.009(11) 0.020(12) -0.003(9) -0.021(13)
-0.030(8) -0.003(11) -0.007(10) 0.005(11) 0.027(11) -0.002(10) -0.008(11)
0.034(10) 0.007(10) 0.011(10) 0.978(3) 1.15(5) 1.145123 1.145123 1.145123
1.145123 2 4.466 2 4.466 2 4.466 3 4.466 4 4.466
O(5) 6.17(6) 0 0.002(19) -0.049(17) -0.10(2) 0.015(17) 0.007(16) 0.012(14)
-0.033(15) 0.011(15) 0.059(16) 0.055(17) 0.011(16) 0.062(13) 0.032(14)
-0.012(14) 0.042(14) -0.005(16) 0.030(16) 0.011(15) 0.027(16) 0.010(16)
-0.022(15) -0.023(15) 0.016(15) -0.009(15) 0.989(3) 0.96(3) 0.959365 0.959365
0.959365 0.959365 2 4.466 2 4.466 2 4.466 3 4.466 4 4.466
O(6) 6.12(5) 0 -0.019(19) -0.12(2) -0.039(17) -0.095(15) 0.002(15) 0.049(14)
0.049(15) -0.007(14) 0.067(13) 0.029(14) -0.001(17) 0.039(18) -0.018(13)
-0.041(17) -0.023(11) 0.027(15) -0.007(15) 0.002(16) 0.024(16) -0.013(15)
0.005(14) 0.039(15) 0.010(15) 0.021(15) 0.989(3) 0.96(3) 0.959365 0.959365
0.959365 0.959365 2 4.466 2 4.466 2 4.466 3 4.466 4 4.466
C(1) 4.31(9) 0 -0.04(5) -0.04(3) 0.07(4) 0.29(3) -0.01(3) -0.04(3) -0.34(3)
0.00(3) 0.56(5) 0.00(4) 0.02(3) 0.47(4) 0.08(4) 0.02(4) 0.00(3) -0.11(4)
0.00(4) -0.01(4) -0.15(4) 0.07(5) -0.08(4) -0.04(4) 0.21(4) 0.02(4) 0.972(7)
0.782(17) 0.782427 0.782427 0.782427 0.782427 2 3.1762 2 3.1762 2 3.1762 3
3.1762 4 3.1762
C(2) 4.19(9) 0 0.13(4) 0.01(3) 0.19(4) 0.13(3) -0.02(2) -0.01(2) -0.03(2)
-0.05(2) 0.33(4) -0.03(3) -0.03(3) 0.07(3) -0.05(3) 0.00(3) -0.33(4) 0.28(4)
0.00(3) -0.03(3) 0.00(4) 0.03(3) 0.04(3) 0.20(4) 0.03(3) -0.12(4) 0.983(6)
0.846(19) 0.846198 0.846198 0.846198 0.846198 2 3.1762 2 3.1762 2 3.1762 3
3.1762 4 3.1762
C(3) 3.99(9) 0 0.06(4) -0.06(4) 0.20(3) 0.17(3) 0.01(2) -0.01(2) 0.03(2)
-0.05(2) 0.36(4) 0.07(3) -0.13(3) 0.02(3) 0.03(3) -0.05(4) -0.35(3) 0.20(4)
-0.05(3) 0.10(3) -0.01(4) -0.02(3) -0.02(3) 0.24(4) 0.12(3) 0.05(4) 0.983(6)
0.846(19) 0.846198 0.846198 0.846198 0.846198 2 3.1762 2 3.1762 2 3.1762 3
3.1762 4 3.1762
C(4) 4.27(10) 0 -0.02(3) -0.06(4) 0.05(5) 0.41(4) 0.00(3) -0.03(3) -0.21(3)
-0.03(3) 0.57(6) 0.00(4) 0.08(4) 0.37(4) 0.01(4) -0.02(3) 0.01(3) -0.09(6)
-0.01(5) 0.13(5) -0.17(5) 0.07(4) -0.01(4) 0.03(4) 0.16(3) -0.01(3) 0.972(7)
0.782(17) 0.782427 0.782427 0.782427 0.782427 2 3.1762 2 3.1762 2 3.1762 3
3.1762 4 3.1762
H(2) 0.62(4) 0 0.034(17) -0.013(13) 0.145(16) 0.10(2) -0.02(2) 0.010(19)
-0.002(17) 0.01(2) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.29(3) 1.5 1.5 1.5 1.5 1.5
0 2 1 2 2 2 3 2 4 2
H(3) 0.65(3) 0 -0.073(16) -0.044(11) 0.165(14) 0.05(2) -0.01(2) -0.073(17)
0.036(17) -0.01(2) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.29(3) 1.5 1.5 1.5 1.5 1.5
0 2 1 2 2 2 3 2 4 2
H(4) 0.68(4) 0 0.032(12) 0.036(14) 0.138(13) 0.070(18) 0.004(18) 0.05(2)
-0.010(19) -0.031(17) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.29(3) 1.5 1.5 1.5 1.5
1.5 0 2 1 2 2 2 3 2 4 2
H(6) 0.62(4) 0 -0.023(14) 0.031(16) 0.157(17) 0.11(2) 0.00(2) 0.04(2) -0.05(2)
0.01(2) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.29(3) 1.5 1.5 1.5 1.5 1.5 0 2 1 2 2 2
3 2 4 2
H(2A) 0.57(4) 0 0 0 0.040(15) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.29(3)
1.5 1.5 1.5 1.5 1.5 0 2 1 2 2 2 3 2 4 2
H(3A) 0.55(4) 0 0 0 0.060(14) 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 0 1.29(3)
1.5 1.5 1.5 1.5 1.5 0 2 1 2 2 2 3 2 4 2

loop_
_atom_local_axes_atom_label
_atom_local_axes_atom0
_atom_local_axes_ax1
_atom_local_axes_atom1
_atom_local_axes_atom2
_atom_local_axes_ax2
O(1) C(1) Z O(1) O(2) Y
O(2) H(2) Z O(2) C(1) Y
O(3) H(3) Z O(3) C(2) Y
O(4) H(4) Z O(4) C(3) Y
O(5) C(4) Z O(5) O(6) Y
O(6) H(6) Z O(6) C(4) Y
C(1) O(1) Z C(1) O(2) Y
C(2) H(2A) Z C(2) O(3) Y
C(3) H(3A) Z C(3) O(4) Y
C(4) O(5) Z C(4) O(6) Y
H(2) O(2) Z H(2) C(1) Y
H(3) O(3) Z H(3) C(2) Y
H(4) O(4) Z H(4) C(3) Y
H(6) O(6) Z H(6) C(4) Y
H(2A) C(2) Z H(2A) O(3) Y
H(3A) C(3) Z H(3A) O(4) Y

_refine_diff_density_max         0.255
_refine_diff_density_min         -0.266
_refine_diff_density_rms         0.059

#----------------------------------------------------------------------------#
#                   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
O(1) C(1) 1.2185(4) 1_555 1_555 yes
O(2) C(1) 1.3131(4) 1_555 1_555 yes
O(2) H(2) 0.982(10) 1_555 1_555 yes
O(3) C(2) 1.3993(3) 1_555 1_555 yes
O(3) H(3) 0.979(8) 1_555 1_555 yes
O(4) C(3) 1.4101(4) 1_555 1_555 yes
O(4) H(4) 0.977(8) 1_555 1_555 yes
O(5) C(4) 1.2103(4) 1_555 1_555 yes
O(6) C(4) 1.3183(4) 1_555 1_555 yes
O(6) H(6) 0.987(9) 1_555 1_555 yes
C(1) C(2) 1.5186(4) 1_555 1_555 yes
C(2) H(2A) 1.083(10) 1_555 1_555 yes
C(3) C(4) 1.5211(4) 1_555 1_555 yes
C(3) H(3A) 1.085(9) 1_555 1_555 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
C(1) O(2) H(2) 115.4(5) 1_555 1_555 1_555 yes
C(2) O(3) H(3) 107.3(4) 1_555 1_555 1_555 yes
C(3) O(4) H(4) 109.7(5) 1_555 1_555 1_555 yes
C(4) O(6) H(6) 113.4(5) 1_555 1_555 1_555 yes
O(1) C(1) O(2) 125.31(3) 1_555 1_555 1_555 yes
O(1) C(1) C(2) 123.47(3) 1_555 1_555 1_555 yes
O(2) C(1) C(2) 111.18(2) 1_555 1_555 1_555 yes
O(3) C(2) C(1) 108.71(2) 1_555 1_555 1_555 yes
O(3) C(2) H(2A) 112.5(5) 1_555 1_555 1_555 yes
C(1) C(2) H(2A) 108.5(5) 1_555 1_555 1_555 yes
O(4) C(3) C(4) 112.14(2) 1_555 1_555 1_555 yes
O(4) C(3) H(3A) 106.8(5) 1_555 1_555 1_555 yes
C(4) C(3) H(3A) 106.3(5) 1_555 1_555 1_555 yes
O(5) C(4) O(6) 125.73(3) 1_555 1_555 1_555 yes
O(5) C(4) C(3) 124.46(3) 1_555 1_555 1_555 yes
O(6) C(4) C(3) 109.80(2) 1_555 1_555 1_555 yes


####################################################################### 
# 
# 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_1iam
_database_code_depnum_ccdc_archive 'CCDC 2020636'
_audit_update_record             
;
2020-07-31 deposited with the CCDC.	2020-12-07 downloaded from the CCDC.
;

_audit_creation_method           SHELXL-2018/3
_shelx_SHELXL_version_number     2018/3
_chemical_name_systematic        'RR-tartaric acid'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C4 H6 O6'
_chemical_formula_sum            'C4 H6 O6'
_chemical_formula_weight         150.09

loop_
_atom_type_symbol
_atom_type_description
_atom_type_scat_dispersion_real
_atom_type_scat_dispersion_imag
_atom_type_scat_source
C C 0.0033 0.0016 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
H H 0.0000 0.0000 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
O O 0.0106 0.0060 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'

_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_H-M_alt        'P 21'
_space_group_name_Hall           'P 2yb'

_shelx_space_group_comment       
;
The symmetry employed for this shelxl refinement is uniquely defined
by the following loop, which should always be used as a source of
symmetry information in preference to the above space-group names.
They are only intended as comments.
;

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

_cell_length_a                   6.1757(2)
_cell_length_b                   5.9211(2)
_cell_length_c                   7.7084(3)
_cell_angle_alpha                90
_cell_angle_beta                 100.434(2)
_cell_angle_gamma                90
_cell_volume                     277.212(17)
_cell_formula_units_Z            2
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    6532
_cell_measurement_theta_min      2.7
_cell_measurement_theta_max      53.6

_exptl_crystal_description       block
_exptl_crystal_colour            colourless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_density_diffrn    1.798
_exptl_crystal_F_000             156
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.300
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.200
_exptl_absorpt_coefficient_mu    0.177
_shelx_estimated_absorpt_T_min   0.949
_shelx_estimated_absorpt_T_max   0.966
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_correction_T_min  0.9569
_exptl_absorpt_correction_T_max  1.0000
_exptl_absorpt_process_details   'SADABS 2014/5'
_exptl_absorpt_special_details   ?
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_monochromator  graphite
_diffrn_measurement_device_type  'Bruker APEX CCD area detector'
_diffrn_measurement_method       'ω scans'
_diffrn_detector_area_resol_mean ?
_diffrn_reflns_number            14423
_diffrn_reflns_av_unetI/netI     0.0335
_diffrn_reflns_av_R_equivalents  0.0281
_diffrn_reflns_limit_h_min       -14
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_k_max       13
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_theta_min         2.687
_diffrn_reflns_theta_max         54.520
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.978
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.978
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.878
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             6147
_reflns_number_gt                5787
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.702
_reflns_Friedel_fraction_max     0.767
_reflns_Friedel_fraction_full    1.000

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

_computing_data_collection       'SMART (Bruker, 2001)'
_computing_cell_refinement       'SMART (Bruker, 2001)'
_computing_data_reduction        'SAINT-Plus (Bruker, 2009)'
_computing_structure_solution    'SHELXS '
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'PLATON (Spek, 2014)'
_computing_publication_material  'SHELXL2013/2 (Sheldrick, 2013)'
_refine_special_details          ?
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0450P)²+0.0040P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   ?
_atom_sites_solution_hydrogens   difmap
_refine_ls_hydrogen_treatment    refxyz
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_abs_structure_details 
;
 Flack x determined using 2224 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.1(2)
_chemical_absolute_configuration rmad
_refine_ls_number_reflns         6147
_refine_ls_number_parameters     109
_refine_ls_number_restraints     1
_refine_ls_R_factor_all          0.0377
_refine_ls_R_factor_gt           0.0352
_refine_ls_wR_factor_ref         0.0882
_refine_ls_wR_factor_gt          0.0864
_refine_ls_goodness_of_fit_ref   1.120
_refine_ls_restrained_S_all      1.120
_refine_ls_shift/su_max          0.003
_refine_ls_shift/su_mean         0.000

loop_
_atom_site_label
_atom_site_type_symbol
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_occupancy
_atom_site_site_symmetry_order
_atom_site_calc_flag
_atom_site_refinement_flags_posn
_atom_site_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O1 O 0.69710(8) 0.72960(9) 0.38996(6) 0.01094(7) Uani 1 1 d . . . . .
O2 O 1.02432(8) 0.68807(9) 0.57122(6) 0.01149(7) Uani 1 1 d . . . . .
H2 H 1.090(3) 0.681(4) 0.477(2) 0.022 Uani 1 1 d . . . . .
O3 O 0.48746(7) 0.75484(9) 0.66178(6) 0.01070(7) Uani 1 1 d . . . . .
H3 H 0.440(3) 0.731(4) 0.754(2) 0.024 Uani 1 1 d . . . . .
O4 O 0.76566(7) 1.14507(8) 0.69271(6) 0.00870(6) Uani 1 1 d . . . . .
H4 H 0.626(3) 1.150(4) 0.661(2) 0.023 Uani 1 1 d . . . . .
O5 O 0.65070(9) 1.13804(10) 1.02195(7) 0.01424(8) Uani 1 1 d . . . . .
O6 O 0.82075(9) 0.80231(10) 1.07903(6) 0.01286(8) Uani 1 1 d . . . . .
H6 H 0.765(3) 0.800(4) 1.169(2) 0.023 Uani 1 1 d . . . . .
C1 C 0.80953(9) 0.71528(9) 0.53681(7) 0.00812(7) Uani 1 1 d . . . . .
C2 C 0.71719(9) 0.73658(10) 0.70605(7) 0.00789(7) Uani 1 1 d . . . . .
H2A H 0.759(3) 0.603(3) 0.783(2) 0.022 Uani 1 1 d . . . . .
C3 C 0.81928(9) 0.95233(9) 0.80000(7) 0.00753(7) Uani 1 1 d . . . . .
H3A H 0.964(3) 0.939(3) 0.820(2) 0.020 Uani 1 1 d . . . . .
C4 C 0.75097(9) 0.97792(10) 0.97898(7) 0.00857(7) Uani 1 1 d . . . . .


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

loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
_geom_bond_site_symmetry_2
_geom_bond_publ_flag
O1 C1 1.2190(7) . ?
O2 C1 1.3147(7) . ?
O2 H2 0.898(16) . ?
O3 C2 1.4020(7) . ?
O3 H3 0.826(17) . ?
O4 C3 1.4131(7) . ?
O4 H4 0.852(16) . ?
O5 C4 1.2109(8) . ?
O6 C4 1.3196(8) . ?
O6 H6 0.830(17) . ?
C1 C2 1.5207(7) . ?
C2 C3 1.5455(8) . ?
C2 H2A 0.992(18) . ?
C3 C4 1.5216(8) . ?
C3 H3A 0.880(18) . ?

loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
C1 O2 H2 115.6(11) . . ?
C2 O3 H3 106.1(12) . . ?
C3 O4 H4 108.2(14) . . ?
C4 O6 H6 111.2(14) . . ?
O1 C1 O2 125.46(5) . . ?
O1 C1 C2 123.49(5) . . ?
O2 C1 C2 111.01(5) . . ?
O3 C2 C1 108.53(4) . . ?
O3 C2 C3 111.05(5) . . ?
C1 C2 C3 106.62(4) . . ?
O3 C2 H2A 110.4(11) . . ?
C1 C2 H2A 110.3(11) . . ?
C3 C2 H2A 109.8(11) . . ?
O4 C3 C4 112.10(4) . . ?
O4 C3 C2 111.15(4) . . ?
C4 C3 C2 110.53(5) . . ?
O4 C3 H3A 107.3(13) . . ?
C4 C3 H3A 106.6(10) . . ?
C2 C3 H3A 109.0(13) . . ?
O5 C4 O6 125.88(5) . . ?
O5 C4 C3 124.44(5) . . ?
O6 C4 C3 109.67(5) . . ?

loop_
_geom_torsion_atom_site_label_1
_geom_torsion_atom_site_label_2
_geom_torsion_atom_site_label_3
_geom_torsion_atom_site_label_4
_geom_torsion
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
O1 C1 C2 O3 4.90(8) . . . . ?
O2 C1 C2 O3 -177.35(5) . . . . ?
O1 C1 C2 C3 -114.80(6) . . . . ?
O2 C1 C2 C3 62.95(6) . . . . ?
O3 C2 C3 O4 -58.57(6) . . . . ?
C1 C2 C3 O4 59.48(6) . . . . ?
O3 C2 C3 C4 66.57(6) . . . . ?
C1 C2 C3 C4 -175.38(4) . . . . ?
O4 C3 C4 O5 4.13(8) . . . . ?
C2 C3 C4 O5 -120.47(7) . . . . ?
O4 C3 C4 O6 -174.82(5) . . . . ?
C2 C3 C4 O6 60.58(6) . . . . ?

_refine_diff_density_max         0.582
_refine_diff_density_min         -0.281
_refine_diff_density_rms         0.084

