Naturally Occurring Chalcones with Aggregation-Induced Emission Enhancement Characteristics.
Budziak-Wieczorek, Iwona; Kamiński, Daniel; Skrzypek, Alicja; Ciołek, Anna; Skrzypek, Tomasz; Janik-Zabrotowicz, Ewa; Arczewska, Marta; Molecules (Basel, Switzerland) 28 (2023) 3412–; doi:10.3390/molecules28083412

data_1569075
_publ_section_title
;
 Naturally Occurring Chalcones with Aggregation-Induced Emission
 Enhancement Characteristics.
;
_journal_issue                   8
_journal_name_full               'Molecules (Basel, Switzerland)'
_journal_page_first              3412
_journal_paper_doi               10.3390/molecules28083412
_journal_volume                  28
_journal_year                    2023
_chemical_compound_source        'Sigma aldrich'
_chemical_formula_moiety         'C16 H14 O4'
_chemical_formula_sum            'C16 H14 O4'
_chemical_formula_weight         270.29
_chemical_name_common            cardamonin
_chemical_name_systematic
(E)-1-(2,4-dihydroxy-6-methoxyphenyl)-3-phenylprop-2-en-1-one
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_atom_sites_solution_primary     dual
_audit_creation_date             2020-04-06
_audit_creation_method
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_cell_angle_alpha                90
_cell_angle_beta                 97.058(3)
_cell_angle_gamma                90
_cell_formula_units_Z            8
_cell_length_a                   25.7114(6)
_cell_length_b                   15.3506(3)
_cell_length_c                   6.8717(2)
_cell_measurement_reflns_used    7329
_cell_measurement_theta_max      68.1850
_cell_measurement_theta_min      4.4990
_cell_volume                     2691.61(11)
_computing_cell_refinement       'CrysAlisPro 1.171.40.45a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.45a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.45a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'olex2.refine (Bourhis et al., 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_pressure         1025
_diffrn_ambient_temperature      293
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean 5.8140
_diffrn_measured_fraction_theta_full 0.9911
_diffrn_measured_fraction_theta_max 0.9911
_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     40.00  86.00   0.50   50.00    --    5.00  40.00 -30.00   92
  2  \w    -71.00  28.00   0.50   50.00    --    5.00  40.00 -30.00  198
  3  \w    -30.00  -4.00   0.50   50.00    --  -90.00  55.00 -49.38   52
  4  \w    -87.00 -38.00   0.50   50.00    --  -90.00  10.00  30.00   98
  5  \w   -148.00-110.00   0.50   50.00    --  -90.00  50.00  60.00   76
  6  \w   -106.00  -1.00   0.50   50.00    --  -90.00  50.00  60.00  210
  7  \w    -27.00  -2.00   0.50   50.00    --  -90.00  40.00 -60.00   50
  8  \w   -101.00 -75.00   0.50   50.00    --  -90.00  40.00 -60.00   52
  9  \w   -159.00-133.00   0.50   50.00    --  -90.00  60.00 -13.06   52
 10  \w   -113.00 -87.00   0.50   50.00    --  -90.00  60.00 -13.06   52
 11  \w    -72.00 -46.00   0.50   50.00    --  -90.00  60.00 -13.06   52
 12  \w   -146.00-120.00   0.50   50.00    --  -90.00  30.00  60.00   52
 13  \w   -100.00 -74.00   0.50   50.00    --  -90.00  30.00  60.00   52
 14  \w    -26.00  -1.00   0.50   50.00    --  -90.00  30.00  60.00   50
 15  \w    -79.00  -3.00   0.50   50.00    --  -90.00  30.00  90.00  152
 16  \w   -179.00-124.00   0.50   50.00    --  -90.00  40.00 -60.00  110
 17  \w   -152.00-126.00   0.50   50.00    --  -90.00  10.00  30.00   52
 18  \w   -175.00 -86.00   0.50   50.00    --  -90.00  60.00  31.77  178
 19  \w    -65.00 -40.00   0.50   50.00    --  -90.00  60.00  31.77   50
 20  \w   -179.00-115.00   0.50   50.00    --  -90.00  59.00 -58.69  128
 21  \w    -64.00 -20.00   0.50   50.00    --  -90.00  59.00 -58.69   88
 22  \w    -89.00 -63.00   0.50   50.00    --  -90.00  40.00   0.00   52
 23  \w    -55.00 -29.00   0.50   50.00    --  -90.00  40.00   0.00   52
 24  \w   -179.00-112.00   0.50   50.00    --  -90.00  20.00  60.00  134
 25  \w    -52.00 -26.00   0.50   50.00    --  -90.00  20.00  60.00   52
 26  \w   -170.00-141.00   0.50   50.00    --  -90.00  40.00  30.00   58
 27  \w   -157.00 -73.00   0.50   50.00    --  -90.00  10.00 150.00  168
 28  \w   -165.00-139.00   0.50   50.00    --  -90.00  50.00 -60.00   52
 29  \w   -108.00 -82.00   0.50   50.00    --  -90.00  50.00 -60.00   52
 30  \w   -174.00-129.00   0.50   50.00    --  -90.00  50.00  30.00   90
 31  \w   -119.00 -94.00   0.50   50.00    --  -90.00  55.00 -49.38   50
 32  \w   -129.00-103.00   0.50   50.00    --  -90.00  59.00 -64.02   52
 33  \w   -177.00-152.00   0.50   50.00    --  -90.00  55.00 -49.38   50
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB AFC11 (RCD3): quarter-chi single'
_diffrn_measurement_method       '\w scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0504692000
_diffrn_orient_matrix_UB_12      -0.0153755000
_diffrn_orient_matrix_UB_13      -0.0948240000
_diffrn_orient_matrix_UB_21      -0.0004153000
_diffrn_orient_matrix_UB_22      0.0960955000
_diffrn_orient_matrix_UB_23      -0.0649081000
_diffrn_orient_matrix_UB_31      0.0331168000
_diffrn_orient_matrix_UB_32      0.0245197000
_diffrn_orient_matrix_UB_33      0.1944672000
_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  0.0355
_diffrn_reflns_av_unetI/netI     0.0339
_diffrn_reflns_limit_h_max       30
_diffrn_reflns_limit_h_min       -26
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       8
_diffrn_reflns_limit_l_min       -7
_diffrn_reflns_number            24772
_diffrn_reflns_theta_full        68.4657
_diffrn_reflns_theta_max         68.47
_diffrn_reflns_theta_min         3.36
_diffrn_source                   'Rotating-anode X-ray tube'
_diffrn_source_type              'Rigaku (Cu) X-ray Source'
_exptl_absorpt_coefficient_mu    0.792
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.90283
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.45a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yelow
_exptl_crystal_density_diffrn    1.3339
_exptl_crystal_description       plate
_exptl_crystal_F_000             1140.0101
_exptl_crystal_recrystallization_method evaporation
_refine_diff_density_max         0.3314
_refine_diff_density_min         -0.3218
_refine_diff_density_rms         0.0769
_refine_ls_d_res_high            0.8288
_refine_ls_d_res_low             13.1527
_refine_ls_extinction_expression Fc^*^=kFc[1+0.001xFc^2^\l^3^/sin(2\q)]^-1/4^
_refine_ls_goodness_of_fit_ref   1.0594
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    52
_refine_ls_number_parameters     368
_refine_ls_number_reflns         4905
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.0594
_refine_ls_R_factor_all          0.0839
_refine_ls_R_factor_gt           0.0678
_refine_ls_shift/su_max          0.0003
_refine_ls_shift/su_mean         0.0000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[\s^2^(Fo^2^)+(0.1056P)^2^+3.5546P] where P=(Fo^2^+2Fc^2^)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.2274
_refine_ls_wR_factor_ref         0.2409
_reflns_Friedel_coverage         0.0
_reflns_limit_h_max              30
_reflns_limit_h_min              -30
_reflns_limit_k_max              18
_reflns_limit_k_min              0
_reflns_limit_l_max              8
_reflns_limit_l_min              0
_reflns_number_gt                3743
_reflns_number_total             4905
_reflns_threshold_expression     I>=2u(I)
_cod_data_source_file            kardamonin.cif
_cod_data_source_block           kardamonin
_cod_original_cell_volume        2691.60(12)
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               1569075
_chemical_oxdiff_formula         C20H20O3
_reflns_odcompleteness_completeness 97.71
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     69.01
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
2.a Aromatic/amide H refined with riding coordinates:
 C00K(H00K), C00R(H00R), C00U(H00U), C00Y(H00Y), C00X(H00X), C00W(H00W),
 C00Q(H00Q), C00G(H00G), C00F(H00F), C011(H011), C012(H012), C014(H014),
 C013(H013), C010(H010), C00I(H00I), C00J(H00J), C00O(H00O), C00V(H00V)
2.b Idealised Me refined as rotating group:
 C00S(H00a,H00b,H00c), C00Z(H00d,H00e,H00h)
2.c Idealised tetrahedral OH refined as rotating group:
 O002(H002), O003(H003), O006(H006), O008(H008)
;
_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 1.673
_oxdiff_exptl_absorpt_empirical_full_min 0.831