Crystal engineering construction of caffeic acid derivatives with potential applications in pharmaceuticals and degradable polymeric materials
Wang, Zhihan; Flores, Quinton; Guo, Hongye; Trevizo, Raquel; Zhang, Xiaochan; Wang, Shihan; CrystEngComm 22 (2020) 7847–7857; doi:10.1039/D0CE01403F

data_7241588
_publ_section_title
;
 Crystal engineering construction of caffeic acid derivatives with
 potential applications in pharmaceuticals and degradable polymeric
 materials
;
_journal_issue                   45
_journal_name_full               CrystEngComm
_journal_page_first              7847
_journal_page_last               7857
_journal_paper_doi               10.1039/D0CE01403F
_journal_volume                  22
_journal_year                    2020
_chemical_formula_moiety         'C18 H16 O8, 2(C4 H8 O2)'
_chemical_formula_sum            'C26 H32 O12'
_chemical_formula_weight         536.51
_chemical_name_common            CBDA10coEA
_space_group_crystal_system      triclinic
_space_group_IT_number           2
_space_group_name_Hall           '-P 1'
_space_group_name_H-M_alt        'P -1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2020-07-22
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2020.03.28 svn.rd84adfe8 for Rigaku Oxford Diffraction, GUI svn.r6032)
;
_audit_update_record
;
2020-10-13 deposited with the CCDC.	2020-10-26 downloaded from the CCDC.
;
_cell_angle_alpha                77.600(2)
_cell_angle_beta                 80.086(2)
_cell_angle_gamma                88.273(2)
_cell_formula_units_Z            1
_cell_length_a                   5.38820(10)
_cell_length_b                   8.4135(2)
_cell_length_c                   14.8002(4)
_cell_measurement_reflns_used    8140
_cell_measurement_temperature    100.00(13)
_cell_measurement_theta_max      77.2950
_cell_measurement_theta_min      5.3590
_cell_volume                     645.49(3)
_computing_cell_refinement       'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_data_collection       'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_data_reduction        'CrysAlisPro 1.171.40.82a (Rigaku OD, 2020)'
_computing_molecular_graphics    'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 1.3-ac4 (Dolomanov et al., 2009)'
_computing_structure_refinement  'XL (Sheldrick, 2008)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      100.00(13)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.964
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  t~exp~   \w     \q     \k     \f   Frames
  1  \w     36.00 123.00   0.50    0.05    --   47.70  22.00 -87.00  174
  2  \w     96.00 178.00   0.50    0.21    --  107.75  22.00 -87.00  164
  3  \w     95.00 178.00   0.50    0.21    --  107.75  30.00-120.00  166
  4  \w     95.00 178.00   0.50    0.21    --  107.75  45.00 -30.00  166
  5  \w     95.00 178.00   0.50    0.21    --  107.75 125.00 -30.00  166
  6  \w     95.00 170.00   0.50    0.21    --  107.75  30.00  60.00  150
  7  \w     94.00 178.00   0.50    0.21    --  107.75  15.00-180.00  168
  8  \w     34.00  95.00   0.50    0.05    --   47.70-125.00  30.00  122
  9  \w     35.00 112.00   0.50    0.21    --  107.75-125.00  90.00  154
 10  \w     35.00 106.00   0.50    0.21    --  107.75 -94.00  30.00  142
 11  \w     35.00  73.00   0.50    0.21    --  107.75 -61.00-120.00   76
 12  \w     35.00 106.00   0.50    0.21    --  107.75 -94.00-180.00  142
 13  \w     35.00  73.00   0.50    0.21    --  107.75 -61.00 -90.00   76
 14  \w     35.00 106.00   0.50    0.21    --  107.75 -94.00 -30.00  142
 15  \w     35.00  73.00   0.50    0.21    --  107.75 -61.00  60.00   76
 16  \w     35.00 105.00   0.50    0.21    --  107.75 -95.00 147.00  140
 17  \w     35.00 112.00   0.50    0.21    --  107.75-125.00 150.00  154
 18  \w     35.00 112.00   0.50    0.21    --  107.75-125.00 -30.00  154
 19  \w     35.00  73.00   0.50    0.21    --  107.75 -61.00 -60.00   76
 20  \w     35.00 106.00   0.50    0.21    --  107.75 -94.00 -90.00  142
 21  \w    -27.00  31.00   0.50    0.05    --   47.70 -22.00 106.00  116
 22  \w     25.00 120.00   0.50    0.05    --   47.70  77.00 150.00  190
 23  \w    -24.00  28.00   0.50    0.05    --  -47.70  19.00  30.00  104
 24  \w    -27.00  28.00   0.50    0.05    --  -47.70  22.00 -87.00  110
 25  \w    -49.00 -14.00   0.50    0.21    --  -86.25  45.00 -90.00   70
 26  \w    -49.00 -14.00   0.50    0.21    --  -86.25  45.00-180.00   70
 27  \w    -49.00 -14.00   0.50    0.21    --  -86.25  45.00   0.00   70
 28  \w    -69.00 -13.00   0.50    0.21    --  -86.25  61.00  60.00  112
 29  \w   -119.00 -25.00   0.50    0.05    --  -47.70 -77.00 -90.00  188
 30  \w   -119.00 -73.00   0.50    0.05    --  -47.70-125.00  30.00   92
 31  \w   -119.00 -33.00   0.50    0.05    --  -47.70 -57.00 -60.00  172
 32  \w   -122.00 -35.00   0.50    0.05    --  -47.70 -22.00 106.00  174
 33  \w   -121.00 -34.00   0.50    0.05    --  -47.70 -38.00  60.00  174
 34  \w   -119.00 -73.00   0.50    0.05    --  -47.70-125.00-120.00   92
 35  \w   -119.00 -25.00   0.50    0.05    --  -47.70 -77.00-150.00  188
 36  \w   -119.00 -25.00   0.50    0.05    --  -47.70 -77.00  30.00  188
 37  \w   -119.00 -33.00   0.50    0.05    --  -47.70 -57.00  60.00  172
 38  \w   -119.00 -25.00   0.50    0.05    --  -47.70 -77.00 -30.00  188
 39  \w   -159.00 -73.00   0.50    0.21    --  -86.25-125.00  60.00  172
 40  \w   -162.00 -74.00   0.50    0.21    --  -86.25 -22.00 106.00  176
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy, Dualflex, HyPix'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0899269000
_diffrn_orient_matrix_UB_12      0.1785812000
_diffrn_orient_matrix_UB_13      -0.0304981000
_diffrn_orient_matrix_UB_21      0.2756955000
_diffrn_orient_matrix_UB_22      -0.0564723000
_diffrn_orient_matrix_UB_23      -0.0047088000
_diffrn_orient_matrix_UB_31      0.0124199000
_diffrn_orient_matrix_UB_32      -0.0083495000
_diffrn_orient_matrix_UB_33      -0.1036499000
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Cu K\a'
_diffrn_radiation_wavelength     1.54184
_diffrn_reflns_av_R_equivalents  0.0404
_diffrn_reflns_av_unetI/netI     0.0261
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.964
_diffrn_reflns_limit_h_max       6
_diffrn_reflns_limit_h_min       -6
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -18
_diffrn_reflns_number            11740
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.964
_diffrn_reflns_theta_full        67.684
_diffrn_reflns_theta_max         76.852
_diffrn_reflns_theta_min         3.102
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'PhotonJet (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.931
_exptl_absorpt_correction_T_max  1.000
_exptl_absorpt_correction_T_min  0.456
_exptl_absorpt_correction_type   gaussian
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.82a (Rigaku Oxford Diffraction, 2020)
Numerical absorption correction based on gaussian integration over
a multifaceted crystal model
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_primary    colourless
_exptl_crystal_density_diffrn    1.380
_exptl_crystal_description       block
_exptl_crystal_F_000             284
_exptl_crystal_recrystallization_method
'Slow evaporation from a mixture of methanol and acetic acid at room temperature'
_exptl_crystal_size_max          0.23
_exptl_crystal_size_mid          0.137
_exptl_crystal_size_min          0.131
_refine_diff_density_max         0.254
_refine_diff_density_min         -0.218
_refine_diff_density_rms         0.043
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.091
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     177
_refine_ls_number_reflns         2628
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.091
_refine_ls_R_factor_all          0.0383
_refine_ls_R_factor_gt           0.0357
_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/[\s^2^(Fo^2^)+(0.0479P)^2^+0.1760P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0954
_refine_ls_wR_factor_ref         0.0982
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2413
_reflns_number_total             2628
_reflns_threshold_expression     'I > 2\s(I)'
_cod_data_source_file            d0ce01403f2.cif
_cod_data_source_block           wan20_01
_cod_database_code               7241588
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         'C26 H32 O12 '
_shelx_estimated_absorpt_t_max   0.888
_shelx_estimated_absorpt_t_min   0.814
_reflns_odcompleteness_completeness 99.70
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     68.13
_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 C(H,H,H) groups, All O(H) groups
2.a Ternary CH refined with riding coordinates:
 C1(H1A), C2(H2)
2.b Secondary CH2 refined with riding coordinates:
 C12(H12A,H12B)
2.c Aromatic/amide H refined with riding coordinates:
 C5(H5), C8(H8), C9(H9)
2.d Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C13(H13A,H13B,H13C)
2.e Idealised tetrahedral OH refined as rotating group:
 O1(H1), O3(H3), O4(H4)
;
_shelx_res_checksum              89117
_olex2_date_sample_data_collection 2020-07-21
_olex2_date_sample_submission    2020-07-21
_olex2_exptl_crystal_mounting_method 'MiTeGen 50 micron loop'
_olex2_submission_original_sample_id CBDAS1
_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 1.653
_oxdiff_exptl_absorpt_empirical_full_min 0.728