# Electronic Supplementary Material (ESI) for CrystEngComm.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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-glutaril
_database_code_depnum_ccdc_archive 'CCDC 1939782'
loop_
_audit_author_name
_audit_author_address
'Jun Xu'
;Tianjin University
China
;
_audit_update_record             
;
2019-07-11 deposited with the CCDC.	2019-09-18 downloaded from the CCDC.
;
_audit_creation_date             2018-11-08
_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         'C7 H6 O3, C5 H8 O4'
_chemical_formula_sum            'C12 H14 O7'
_chemical_formula_weight         270.23
_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      monoclinic
_space_group_IT_number           14
_space_group_name_H-M_alt        'P 1 21/n 1'
_space_group_name_Hall           '-P 2yn'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y-1/2, z-1/2'

_cell_length_a                   8.6867(4)
_cell_length_b                   15.1019(6)
_cell_length_c                   9.9125(5)
_cell_angle_alpha                90
_cell_angle_beta                 105.478(5)
_cell_angle_gamma                90
_cell_volume                     1253.22(10)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    4474
_cell_measurement_temperature    159.99(10)
_cell_measurement_theta_max      28.6630
_cell_measurement_theta_min      2.5170
_shelx_estimated_absorpt_T_max   0.994
_shelx_estimated_absorpt_T_min   0.965
_exptl_absorpt_coefficient_mu    0.119
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.39743
_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    1.432
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             568
_exptl_crystal_size_max          0.3
_exptl_crystal_size_mid          0.2
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0454
_diffrn_reflns_av_unetI/netI     0.0391
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.844
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       20
_diffrn_reflns_limit_k_min       -20
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_number            13894
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.844
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.041
_diffrn_reflns_theta_min         2.523
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      159.99(10)
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.844
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -41.00  62.00   0.50    4.84    --  -13.65  57.00   1.00  206
  2  ω     39.00  97.00   0.50    4.84    --   12.17 178.00-120.00  116
  3  ω     39.00  97.00   0.50    4.84    --   12.17 178.00-150.00  116
  4  ω    -89.00  14.00   0.50    4.84    --  -13.65 -57.00-140.00  206
  5  ω     36.00  68.00   0.50    4.84    --   12.17-178.00 -60.00   64
  6  ω    -95.00  19.00   0.50    4.84    --  -13.65 -37.00   0.00  228
;
_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      0.0147769000
_diffrn_orient_matrix_UB_12      -0.0111082000
_diffrn_orient_matrix_UB_13      -0.0649284000
_diffrn_orient_matrix_UB_21      -0.0605037000
_diffrn_orient_matrix_UB_22      0.0299938000
_diffrn_orient_matrix_UB_23      -0.0348113000
_diffrn_orient_matrix_UB_31      0.0574875000
_diffrn_orient_matrix_UB_32      0.0343606000
_diffrn_orient_matrix_UB_33      0.0091498000
_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                2235
_reflns_number_total             3101
_reflns_odcompleteness_completeness 99.93
_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         0.275
_refine_diff_density_min         -0.297
_refine_diff_density_rms         0.059
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.044
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         3101
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0723
_refine_ls_R_factor_gt           0.0486
_refine_ls_restrained_S_all      1.044
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0781P)²+0.1653P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1254
_refine_ls_wR_factor_ref         0.1402
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
2. Others
 Sof(H3)=1-FVAR(1)
 Sof(H2)=FVAR(1)
3.a Secondary CH2 refined with riding coordinates:
 C11(H11A,H11B), C10(H10A,H10B), C9(H9A,H9B)
3.b Aromatic/amide H refined with riding coordinates:
 C2(H2A), C5(H5), C6(H6), C3(H3A)
;
_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
O1 O 0.62733(15) 0.54772(7) 0.38780(13) 0.0353(3) Uani 1 1 d . . . . .
O3 O 1.04863(14) 0.89253(8) 0.53640(13) 0.0334(3) Uani 1 1 d . . . . .
O6 O 0.04147(15) 0.86681(8) 0.19838(13) 0.0391(3) Uani 1 1 d . . . . .
O5 O 0.17188(16) 0.44577(7) 0.20653(14) 0.0408(3) Uani 1 1 d . . . . .
O2 O 0.81502(15) 0.95312(8) 0.42150(13) 0.0362(3) Uani 1 1 d . . . . .
O7 O -0.21415(16) 0.87345(8) 0.07874(13) 0.0393(3) Uani 1 1 d . . . . .
O4 O 0.31740(14) 0.56829(8) 0.25858(14) 0.0437(4) Uani 1 1 d . . . . .
C7 C 0.82839(19) 0.79808(9) 0.44646(15) 0.0239(3) Uani 1 1 d . . . . .
C1 C 0.90323(19) 0.88633(10) 0.46993(15) 0.0261(3) Uani 1 1 d . . . . .
C2 C 0.91866(19) 0.72293(10) 0.49703(15) 0.0258(3) Uani 1 1 d . . . . .
H2A H 1.025965 0.728760 0.544710 0.031 Uiso 1 1 calc R . . . .
C5 C 0.59814(19) 0.70578(10) 0.35332(16) 0.0262(4) Uani 1 1 d . . . . .
H5 H 0.490859 0.699832 0.305630 0.031 Uiso 1 1 calc R . . . .
C4 C 0.6899(2) 0.63121(9) 0.40504(16) 0.0264(3) Uani 1 1 d . . . . .
C6 C 0.66831(19) 0.78848(9) 0.37367(16) 0.0254(3) Uani 1 1 d . . . . .
H6 H 0.608037 0.838306 0.338390 0.030 Uiso 1 1 calc R . . . .
C12 C -0.08045(19) 0.82938(10) 0.13756(16) 0.0274(3) Uani 1 1 d . . . . .
C11 C -0.09845(19) 0.73110(10) 0.12128(17) 0.0277(4) Uani 1 1 d . . . . .
H11A H -0.132908 0.716662 0.022419 0.033 Uiso 1 1 calc R . . . .
H11B H -0.180770 0.711278 0.163921 0.033 Uiso 1 1 calc R . . . .
C8 C 0.1894(2) 0.53276(10) 0.21496(16) 0.0281(4) Uani 1 1 d . . . . .
C10 C 0.05554(18) 0.68194(10) 0.18770(16) 0.0267(4) Uani 1 1 d . . . . .
H10A H 0.087132 0.693461 0.287590 0.032 Uiso 1 1 calc R . . . .
H10B H 0.139567 0.703642 0.148637 0.032 Uiso 1 1 calc R . . . .
C3 C 0.8495(2) 0.63962(10) 0.47668(16) 0.0284(4) Uani 1 1 d . . . . .
H3A H 0.909869 0.589652 0.510934 0.034 Uiso 1 1 calc R . . . .
C9 C 0.0359(2) 0.58253(10) 0.16269(18) 0.0323(4) Uani 1 1 d . . . . .
H9A H -0.041317 0.560251 0.209263 0.039 Uiso 1 1 calc R . . . .
H9B H -0.006139 0.571756 0.063160 0.039 Uiso 1 1 calc R . . . .
H1 H 0.527(3) 0.5503(14) 0.345(2) 0.051(6) Uiso 1 1 d . . . . .
H7 H -0.191(3) 0.9305(17) 0.084(2) 0.068(7) Uiso 1 1 d . . . . .
H5A H 0.272(4) 0.4192(18) 0.240(2) 0.076(8) Uiso 1 1 d . . . . .
H2 H 0.854(5) 1.000(3) 0.434(4) 0.029(15) Uiso 0.51(6) 1 d . . P A 1
H3 H 1.077(7) 0.943(4) 0.547(5) 0.05(2) Uiso 0.49(6) 1 d . . P A 2


_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 C4 1.3655(17) . ?
O1 H1 0.86(2) . ?
O3 C1 1.263(2) . ?
O3 H3 0.80(7) . ?
O6 C12 1.2099(19) . ?
O5 C8 1.3225(19) . ?
O5 H5A 0.94(3) . ?
O2 C1 1.2802(19) . ?
O2 H2 0.78(5) . ?
O7 C12 1.331(2) . ?
O7 H7 0.88(3) . ?
O4 C8 1.2059(19) . ?
C7 C1 1.474(2) . ?
C7 C2 1.394(2) . ?
C7 C6 1.393(2) . ?
C2 H2A 0.9300 . ?
C2 C3 1.386(2) . ?
C5 H5 0.9300 . ?
C5 C4 1.396(2) . ?
C5 C6 1.381(2) . ?
C4 C3 1.385(2) . ?
C6 H6 0.9300 . ?
C12 C11 1.497(2) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C11 C10 1.518(2) . ?
C8 C9 1.498(2) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C10 C9 1.524(2) . ?
C3 H3A 0.9300 . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?

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 O1 H1 109.6(15) . . ?
C1 O3 H3 112(4) . . ?
C8 O5 H5A 108.8(17) . . ?
C1 O2 H2 118(3) . . ?
C12 O7 H7 107.6(17) . . ?
C2 C7 C1 119.81(14) . . ?
C6 C7 C1 120.88(13) . . ?
C6 C7 C2 119.31(13) . . ?
O3 C1 O2 123.54(14) . . ?
O3 C1 C7 119.16(14) . . ?
O2 C1 C7 117.30(14) . . ?
C7 C2 H2A 119.8 . . ?
C3 C2 C7 120.41(15) . . ?
C3 C2 H2A 119.8 . . ?
C4 C5 H5 120.3 . . ?
C6 C5 H5 120.3 . . ?
C6 C5 C4 119.32(15) . . ?
O1 C4 C5 122.01(15) . . ?
O1 C4 C3 117.34(14) . . ?
C3 C4 C5 120.65(13) . . ?
C7 C6 H6 119.6 . . ?
C5 C6 C7 120.71(14) . . ?
C5 C6 H6 119.6 . . ?
O6 C12 O7 122.03(15) . . ?
O6 C12 C11 124.71(15) . . ?
O7 C12 C11 113.26(14) . . ?
C12 C11 H11A 109.1 . . ?
C12 C11 H11B 109.1 . . ?
C12 C11 C10 112.56(13) . . ?
H11A C11 H11B 107.8 . . ?
C10 C11 H11A 109.1 . . ?
C10 C11 H11B 109.1 . . ?
O5 C8 C9 113.56(14) . . ?
O4 C8 O5 122.97(15) . . ?
O4 C8 C9 123.46(14) . . ?
C11 C10 H10A 109.4 . . ?
C11 C10 H10B 109.4 . . ?
C11 C10 C9 111.32(12) . . ?
H10A C10 H10B 108.0 . . ?
C9 C10 H10A 109.4 . . ?
C9 C10 H10B 109.4 . . ?
C2 C3 H3A 120.2 . . ?
C4 C3 C2 119.60(14) . . ?
C4 C3 H3A 120.2 . . ?
C8 C9 C10 112.78(13) . . ?
C8 C9 H9A 109.0 . . ?
C8 C9 H9B 109.0 . . ?
C10 C9 H9A 109.0 . . ?
C10 C9 H9B 109.0 . . ?
H9A C9 H9B 107.8 . . ?

_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 1.861
_oxdiff_exptl_absorpt_empirical_full_min 0.537
