# 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_phba_malonic
_database_code_depnum_ccdc_archive 'CCDC 2008771'
loop_
_audit_author_name
_audit_author_address
'Jun Xu'
;Tianjin University
China
;
_audit_update_record             
;
2020-06-09 deposited with the CCDC.	2020-07-22 downloaded from the CCDC.
;
_audit_creation_date             2018-11-09
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2018/3
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C3 H4 O4, C7 H6 O3'
_chemical_formula_sum            'C10 H10 O7'
_chemical_formula_weight         242.18
_chemical_melting_point          ?
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'

_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.
;
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_H-M_alt        'P -1'
_space_group_name_Hall           '-P 1'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'

_cell_length_a                   5.7358(2)
_cell_length_b                   7.1947(2)
_cell_length_c                   13.6224(4)
_cell_angle_alpha                102.176(2)
_cell_angle_beta                 92.789(2)
_cell_angle_gamma                108.166(3)
_cell_volume                     518.15(3)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3491
_cell_measurement_temperature    299.57(10)
_cell_measurement_theta_max      27.2760
_cell_measurement_theta_min      3.7320
_shelx_estimated_absorpt_T_max   0.995
_shelx_estimated_absorpt_T_min   0.948
_exptl_absorpt_coefficient_mu    0.135
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.68103
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.39.43d (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            colourless
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.552
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             252
_exptl_crystal_size_max          0.4
_exptl_crystal_size_mid          0.4
_exptl_crystal_size_min          0.04
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0435
_diffrn_reflns_av_unetI/netI     0.0384
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.862
_diffrn_reflns_limit_h_max       8
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       9
_diffrn_reflns_limit_k_min       -9
_diffrn_reflns_limit_l_max       18
_diffrn_reflns_limit_l_min       -17
_diffrn_reflns_number            11783
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.862
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.114
_diffrn_reflns_theta_min         3.068
_diffrn_ambient_environment      air
_diffrn_ambient_temperature      299.57(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.862
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     39.00  97.00   0.50    0.18    --   12.17 178.00-180.00  116
  2  ω     39.00  97.00   0.50    0.18    --   12.17 178.00-150.00  116
  3  ω    -69.00  44.00   0.50    0.18    --   12.17 -37.00  30.00  226
  4  ω    -64.00  38.00   0.50    0.18    --   12.17 -55.00-125.00  204
  5  ω    -26.00  31.00   0.50    0.18    --  -13.81 -99.00-150.00  114
  6  ω    -99.00 -38.00   0.50    0.18    --  -13.81-178.00  90.00  122
  7  ω    -99.00 -38.00   0.50    0.18    --  -13.81-178.00   0.00  122
  8  ω    -99.00 -38.00   0.50    0.18    --  -13.81-178.00-120.00  122
  9  ω    -26.00  31.00   0.50    0.18    --  -13.81 -99.00 -30.00  114
 10  ω    -89.00  13.00   0.50    0.18    --  -13.81 -57.00 120.00  204
 11  ω    -89.00 -28.00   0.50    0.18    --  -13.81 -77.00 120.00  122
 12  ω    -14.00  88.00   0.50    0.18    --   12.17  55.00  17.00  204
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  
'XtaLAB Synergy, Single source at offset/far, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0738224000
_diffrn_orient_matrix_UB_12      0.0483106000
_diffrn_orient_matrix_UB_13      -0.0209170000
_diffrn_orient_matrix_UB_21      -0.0952356000
_diffrn_orient_matrix_UB_22      -0.0386227000
_diffrn_orient_matrix_UB_23      0.0289064000
_diffrn_orient_matrix_UB_31      0.0517688000
_diffrn_orient_matrix_UB_32      0.0871082000
_diffrn_orient_matrix_UB_33      0.0400995000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Mo) X-ray Source'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_full    .
_reflns_Friedel_fraction_max     .
_reflns_number_gt                1702
_reflns_number_total             2630
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_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.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.39.43d (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.39.43d (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.39.43d (Rigaku OD, 2018)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_refine_diff_density_max         0.172
_refine_diff_density_min         -0.239
_refine_diff_density_rms         0.050
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.021
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     164
_refine_ls_number_reflns         2630
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0797
_refine_ls_R_factor_gt           0.0476
_refine_ls_restrained_S_all      1.021
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0583P)²+0.0637P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1101
_refine_ls_wR_factor_ref         0.1338
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All O(H) groups
2.a Secondary CH2 refined with riding coordinates:
 C3(H3a,H3b)
2.b Aromatic/amide H refined with riding coordinates:
 C10(H10), C9(H9), C13(H13), C12(H12)
2.c Idealised tetrahedral OH refined as rotating group:
 O17(H17), O15(H15)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_atom_sites_solution_secondary   ?
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
O5 O 0.2207(2) 0.71654(19) 0.23626(8) 0.0479(3) Uani 1 1 d . . . . .
O6 O 0.6282(2) 0.8353(2) 0.24041(9) 0.0557(4) Uani 1 1 d . . . . .
O16 O 0.6560(2) 0.8348(2) 0.42799(8) 0.0549(4) Uani 1 1 d . . . . .
O17 O 0.6445(2) 0.6886(2) 0.87113(8) 0.0549(4) Uani 1 1 d . . . . .
H17 H 0.792404 0.729556 0.891914 0.082 Uiso 1 1 calc GR . . . .
O15 O 0.2555(2) 0.6890(2) 0.43348(8) 0.0559(4) Uani 1 1 d . . . . .
H15 H 0.246932 0.701986 0.375170 0.084 Uiso 1 1 calc GR . . . .
O1 O 0.1308(2) 0.8024(2) -0.04963(8) 0.0577(4) Uani 1 1 d . . . . .
O7 O -0.0517(2) 0.7021(2) 0.07562(10) 0.0640(4) Uani 1 1 d . . . . .
C8 C 0.5282(3) 0.7439(2) 0.57897(10) 0.0369(4) Uani 1 1 d . . . . .
C11 C 0.6135(3) 0.7100(3) 0.77513(11) 0.0398(4) Uani 1 1 d . . . . .
C14 C 0.4884(3) 0.7609(2) 0.47416(11) 0.0393(4) Uani 1 1 d . . . . .
C4 C 0.4062(3) 0.7800(2) 0.19554(11) 0.0394(4) Uani 1 1 d . . . . .
C3 C 0.3954(3) 0.7986(3) 0.08789(11) 0.0441(4) Uani 1 1 d . . . . .
H3A H 0.505010 0.931367 0.086733 0.053 Uiso 1 1 calc R . . . .
H3B H 0.461969 0.701331 0.049485 0.053 Uiso 1 1 calc R . . . .
C2 C 0.1491(3) 0.7696(3) 0.03342(11) 0.0418(4) Uani 1 1 d . . . . .
C10 C 0.8094(3) 0.8000(3) 0.72693(12) 0.0444(4) Uani 1 1 d . . . . .
H10 H 0.969619 0.849250 0.760312 0.053 Uiso 1 1 calc R . . . .
C9 C 0.7665(3) 0.8165(3) 0.62914(12) 0.0447(4) Uani 1 1 d . . . . .
H9 H 0.898361 0.876757 0.596630 0.054 Uiso 1 1 calc R . . . .
C13 C 0.3333(3) 0.6554(3) 0.62813(12) 0.0449(4) Uani 1 1 d . . . . .
H13 H 0.172961 0.606744 0.594925 0.054 Uiso 1 1 calc R . . . .
C12 C 0.3745(3) 0.6387(3) 0.72578(12) 0.0486(4) Uani 1 1 d . . . . .
H12 H 0.242505 0.579693 0.758524 0.058 Uiso 1 1 calc R . . . .
H6 H 0.630(4) 0.830(3) 0.3071(18) 0.085(7) Uiso 1 1 d . . . . .
H7 H 0.006(5) 0.699(4) 0.1398(19) 0.108(9) Uiso 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
O5 C4 1.2287(19) . ?
O6 C4 1.2881(19) . ?
O6 H6 0.92(2) . ?
O16 C14 1.2179(19) . ?
O17 H17 0.8200 . ?
O17 C11 1.3584(18) . ?
O15 H15 0.8200 . ?
O15 C14 1.3173(19) . ?
O1 C2 1.2095(18) . ?
O7 C2 1.314(2) . ?
O7 H7 0.93(3) . ?
C8 C14 1.471(2) . ?
C8 C9 1.386(2) . ?
C8 C13 1.383(2) . ?
C11 C10 1.382(2) . ?
C11 C12 1.386(2) . ?
C4 C3 1.500(2) . ?
C3 H3A 0.9700 . ?
C3 H3B 0.9700 . ?
C3 C2 1.496(2) . ?
C10 H10 0.9300 . ?
C10 C9 1.379(2) . ?
C9 H9 0.9300 . ?
C13 H13 0.9300 . ?
C13 C12 1.376(2) . ?
C12 H12 0.9300 . ?

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
C4 O6 H6 111.8(15) . . ?
C11 O17 H17 109.5 . . ?
C14 O15 H15 109.5 . . ?
C2 O7 H7 104.7(17) . . ?
C9 C8 C14 119.23(15) . . ?
C13 C8 C14 121.44(15) . . ?
C13 C8 C9 119.33(14) . . ?
O17 C11 C10 122.43(15) . . ?
O17 C11 C12 117.46(15) . . ?
C10 C11 C12 120.12(14) . . ?
O16 C14 O15 122.22(14) . . ?
O16 C14 C8 123.20(15) . . ?
O15 C14 C8 114.58(14) . . ?
O5 C4 O6 123.54(14) . . ?
O5 C4 C3 123.01(14) . . ?
O6 C4 C3 113.45(14) . . ?
C4 C3 H3A 107.8 . . ?
C4 C3 H3B 107.8 . . ?
H3A C3 H3B 107.1 . . ?
C2 C3 C4 118.06(14) . . ?
C2 C3 H3A 107.8 . . ?
C2 C3 H3B 107.8 . . ?
O1 C2 O7 119.42(15) . . ?
O1 C2 C3 121.34(15) . . ?
O7 C2 C3 119.22(13) . . ?
C11 C10 H10 120.1 . . ?
C9 C10 C11 119.77(15) . . ?
C9 C10 H10 120.1 . . ?
C8 C9 H9 119.8 . . ?
C10 C9 C8 120.44(16) . . ?
C10 C9 H9 119.8 . . ?
C8 C13 H13 119.7 . . ?
C12 C13 C8 120.58(15) . . ?
C12 C13 H13 119.7 . . ?
C11 C12 H12 120.1 . . ?
C13 C12 C11 119.76(16) . . ?
C13 C12 H12 120.1 . . ?

_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details 
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.560
_oxdiff_exptl_absorpt_empirical_full_min 0.723
