# Electronic Supplementary Material (ESI) for Organic & Biomolecular Chemistry.
# This journal is © The Royal Society of Chemistry 2021

####################################################################### 
# 
# 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_krause1w
_database_code_depnum_ccdc_archive 'CCDC 2060196'
loop_
_audit_author_name
_audit_author_address
'Eric Sperlich'
;University Potsdam
Germany
;
_audit_update_record             
;
2021-02-01 deposited with the CCDC.	2021-04-15 downloaded from the CCDC.
;
_audit_creation_method           SHELXL-2018/3
_chemical_name_systematic        
;
(E)-2-(4-methoxybenzylidene)-4-isopropoxy-4-oxobutanoic acid
;
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H18 O5'
_chemical_formula_sum            'C15 H18 O5'
_chemical_formula_weight         278.29

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           15
_space_group_name_H-M_alt        'I 2/a'
_space_group_name_Hall           '-I 2ya'

_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+1/2, y, -z'
'x+1/2, y+1/2, z+1/2'
'-x+1, y+1/2, -z+1/2'
'-x, -y, -z'
'x-1/2, -y, z'
'-x+1/2, -y+1/2, -z+1/2'
'x, -y+1/2, z+1/2'

_cell_length_a                   29.6153(12)
_cell_length_b                   4.86890(10)
_cell_length_c                   20.5000(9)
_cell_angle_alpha                90
_cell_angle_beta                 104.698(3)
_cell_angle_gamma                90
_cell_volume                     2859.25(18)
_cell_formula_units_Z            8
_cell_measurement_temperature    210(2)
_cell_measurement_reflns_used    48841
_cell_measurement_theta_min      2.78
_cell_measurement_theta_max      33.43

_exptl_crystal_description       prism
_exptl_crystal_colour            colorless
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.293
_exptl_crystal_F_000             1184
_exptl_transmission_factor_min   ?
_exptl_transmission_factor_max   ?
_exptl_crystal_size_max          0.900
_exptl_crystal_size_mid          0.300
_exptl_crystal_size_min          0.250
_exptl_crystal_size_rad          0.253
_exptl_absorpt_coefficient_mu    0.097
_shelx_estimated_absorpt_T_min   0.918
_shelx_estimated_absorpt_T_max   0.976
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
STOE LANA, absorption correction by scaling of reflection intensities.
J. Koziskova, F. Hahn, J. Richter, J. Kozisek, "Comparison of different
absorption corrections on the model structure of tetrakis(μ₂-acetato)-
diaqua-di-copper(II)", Acta Chimica Slovaca, vol. 9, no. 2, 2016, pp. 136 - 140.
;
_exptl_absorpt_correction_T_min  0.3647
_exptl_absorpt_correction_T_max  1.0000

_exptl_special_details           
;
 The crystal was embedded in perfluoropolyalkylether oil. 
;

_diffrn_measurement_device       'Eulerian 4-circle diffractometer'
_diffrn_measurement_device_type  'STOE STADIVARI'
_diffrn_detector                 Pilatus200K
_diffrn_detector_type            'DECTRIS PILATUS 200K'
_diffrn_radiation_source         'Genix Microfocus'
_diffrn_source_voltage           50
_diffrn_source_current           1.000
_diffrn_source_power             0.050
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_monochromator  'graded multilayer mirror'
_diffrn_radiation_collimation    '0.3 mm diameter'
_diffrn_ambient_temperature      210
_diffrn_measurement_method       'rotation method, ω scans'
_diffrn_measurement_details      
; 5806 frames, detector distance = 60 mm
;

_diffrn_reflns_number            74300
_diffrn_reflns_av_unetI/netI     0.0161
_diffrn_reflns_av_R_equivalents  0.0391
_diffrn_reflns_limit_h_min       -41
_diffrn_reflns_limit_h_max       41
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_theta_min         2.844
_diffrn_reflns_theta_max         29.999
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measured_fraction_theta_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_point_group_measured_fraction_full 0.997
_reflns_number_total             4156
_reflns_number_gt                3151
_reflns_threshold_expression     'I > 2σ(I)'
_reflns_Friedel_coverage         0.000
_reflns_Friedel_fraction_max     .
_reflns_Friedel_fraction_full    .

_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       
;
X-Area Pilatus3_SV 1.31.153.0 (STOE, 2018)
;
_computing_cell_refinement       
;
X-Area Recipe 1.33.0.0 (STOE, 2015)
;
_computing_data_reduction        
;
X-Area Integrate 1.74.2.0 (STOE, 2018)
X-Area LANA 1.75.3.0 (STOE, 2018)
;
_computing_structure_solution    'SHELXS-2013/1 (Sheldrick, 2013)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_molecular_graphics    'Diamond (Blankenburg, 2020)'
_computing_publication_material  
;
STOE & Cie GmbH, X-Area, software package for collecting single-crystal or
multi-domain crystal data on STOE area-detector diffractometers, for image 
processing, for the correction and scaling of reflection intensities and 
for outlier rejection, version 1.86, Darmstadt 2018
;

_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0633P)²+0.6825P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   geom
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         4156
_refine_ls_number_parameters     216
_refine_ls_number_restraints     3
_refine_ls_R_factor_all          0.0564
_refine_ls_R_factor_gt           0.0415
_refine_ls_wR_factor_ref         0.1204
_refine_ls_wR_factor_gt          0.1129
_refine_ls_goodness_of_fit_ref   1.070
_refine_ls_restrained_S_all      1.069
_refine_ls_shift/su_max          0.001
_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
C1 C 0.46535(3) 0.2862(2) 0.53191(5) 0.0309(2) Uani 1 1 d . . . . .
C2 C 0.43713(3) 0.5028(2) 0.55340(5) 0.0303(2) Uani 1 1 d . . . . .
C3 C 0.40387(4) 0.6473(2) 0.49603(5) 0.0324(2) Uani 1 1 d . . . . .
H3A H 0.418368 0.664238 0.458241 0.039 Uiso 1 1 calc R U . . .
H3B H 0.398075 0.833041 0.510443 0.039 Uiso 1 1 calc R U . . .
C4 C 0.35787(4) 0.4990(2) 0.47230(5) 0.0344(2) Uani 1 1 d . . . . .
C5 C 0.44342(3) 0.5538(2) 0.61967(5) 0.0321(2) Uani 1 1 d . . . . .
H5 H 0.465791 0.441676 0.648257 0.039 Uiso 1 1 calc R U . . .
C6 C 0.42125(3) 0.7546(2) 0.65450(5) 0.0319(2) Uani 1 1 d . . . . .
C7 C 0.44464(4) 0.8269(2) 0.72025(6) 0.0388(2) Uani 1 1 d . . . . .
H7 H 0.473265 0.741266 0.740176 0.047 Uiso 1 1 calc R U . . .
C8 C 0.42739(4) 1.0198(3) 0.75735(6) 0.0404(3) Uani 1 1 d . . . . .
H8 H 0.444203 1.064855 0.801411 0.048 Uiso 1 1 calc R U . . .
C9 C 0.38501(4) 1.1455(2) 0.72867(6) 0.0374(2) Uani 1 1 d . . . . .
C10 C 0.36072(4) 1.0746(3) 0.66370(6) 0.0456(3) Uani 1 1 d . . . . .
H10 H 0.331966 1.159568 0.644174 0.055 Uiso 1 1 calc R U . . .
C11 C 0.37812(4) 0.8817(3) 0.62737(6) 0.0408(3) Uani 1 1 d . . . . .
H11 H 0.360800 0.834606 0.583715 0.049 Uiso 1 1 calc R U . . .
C12 C 0.38796(6) 1.4116(3) 0.82732(7) 0.0576(4) Uani 1 1 d . . . . .
H12A H 0.418415 1.486941 0.828092 0.086 Uiso 1 1 calc R U . . .
H12B H 0.391715 1.249914 0.855843 0.086 Uiso 1 1 calc R U . . .
H12C H 0.369729 1.547974 0.843890 0.086 Uiso 1 1 calc R U . . .
O1 O 0.46129(3) 0.23506(16) 0.47204(4) 0.03821(19) Uani 1 1 d . . . . .
O2 O 0.49519(3) 0.15253(17) 0.58050(4) 0.0399(2) Uani 1 1 d . . . . .
H2 H 0.5107(5) 0.024(3) 0.5620(4) 0.060 Uiso 1 1 calc R U . . .
O3 O 0.34722(4) 0.2931(2) 0.49599(6) 0.0647(3) Uani 1 1 d . . . . .
O4 O 0.36445(3) 1.3379(2) 0.75981(4) 0.0515(2) Uani 1 1 d . . . . .
O5 O 0.33036(3) 0.6265(2) 0.41973(5) 0.0569(3) Uani 1 1 d . . . . .
C13A C 0.2811(5) 0.531(3) 0.3980(6) 0.0437(18) Uani 0.410(6) 1 d D . P A 1
H13A H 0.273727 0.404737 0.431798 0.052 Uiso 0.410(6) 1 calc R U P A 1
C14A C 0.24682(15) 0.7682(9) 0.3832(3) 0.0675(14) Uani 0.410(6) 1 d D . P A 1
H14A H 0.255487 0.892686 0.351454 0.101 Uiso 0.410(6) 1 calc R U P A 1
H14B H 0.247478 0.865518 0.424699 0.101 Uiso 0.410(6) 1 calc R U P A 1
H14C H 0.215616 0.698258 0.363929 0.101 Uiso 0.410(6) 1 calc R U P A 1
C15A C 0.27998(18) 0.3801(17) 0.3329(3) 0.088(2) Uani 0.410(6) 1 d D . P A 1
H15A H 0.292264 0.498438 0.303420 0.131 Uiso 0.410(6) 1 calc R U P A 1
H15B H 0.248064 0.330015 0.310786 0.131 Uiso 0.410(6) 1 calc R U P A 1
H15C H 0.298921 0.215391 0.342800 0.131 Uiso 0.410(6) 1 calc R U P A 1
C13B C 0.2853(4) 0.503(3) 0.3874(5) 0.069(3) Uani 0.590(6) 1 d D . P A 2
H13B H 0.287289 0.300978 0.393474 0.083 Uiso 0.590(6) 1 calc R U P A 2
C14B C 0.25423(12) 0.6196(14) 0.4273(3) 0.125(3) Uani 0.590(6) 1 d D . P A 2
H14D H 0.257760 0.817677 0.429624 0.187 Uiso 0.590(6) 1 calc R U P A 2
H14E H 0.262654 0.543581 0.472474 0.187 Uiso 0.590(6) 1 calc R U P A 2
H14F H 0.222050 0.573573 0.405626 0.187 Uiso 0.590(6) 1 calc R U P A 2
C15B C 0.27381(17) 0.5680(14) 0.3159(2) 0.1140(19) Uani 0.590(6) 1 d D . P A 2
H15D H 0.276876 0.764302 0.310153 0.137 Uiso 0.590(6) 1 calc R U P A 2
H15E H 0.241955 0.512219 0.295221 0.137 Uiso 0.590(6) 1 calc R U P A 2
H15F H 0.294917 0.471165 0.294684 0.137 Uiso 0.590(6) 1 calc R U 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
C1 O1 1.2278(13) . ?
C1 O2 1.3228(12) . ?
C1 C2 1.4804(14) . ?
C2 C5 1.3467(14) . ?
C2 C3 1.5035(14) . ?
C3 C4 1.5089(15) . ?
C3 H3A 0.9800 . ?
C3 H3B 0.9800 . ?
C4 O3 1.1907(14) . ?
C4 O5 1.3287(13) . ?
C5 C6 1.4608(14) . ?
C5 H5 0.9400 . ?
C6 C7 1.3952(15) . ?
C6 C11 1.4013(15) . ?
C7 C8 1.3852(16) . ?
C7 H7 0.9400 . ?
C8 C9 1.3859(16) . ?
C8 H8 0.9400 . ?
C9 O4 1.3614(14) . ?
C9 C10 1.3871(16) . ?
C10 C11 1.3775(16) . ?
C10 H10 0.9400 . ?
C11 H11 0.9400 . ?
C12 O4 1.4283(16) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C12 H12C 0.9700 . ?
O2 H2 0.914(17) . ?
O5 C13B 1.460(13) . ?
O5 C13A 1.489(15) . ?
C13A C15A 1.516(15) . ?
C13A C14A 1.517(16) . ?
C13A H13A 0.9900 . ?
C14A H14A 0.9700 . ?
C14A H14B 0.9700 . ?
C14A H14C 0.9700 . ?
C15A H15A 0.9700 . ?
C15A H15B 0.9700 . ?
C15A H15C 0.9700 . ?
C13B C15B 1.453(10) . ?
C13B C14B 1.490(12) . ?
C13B H13B 0.9900 . ?
C14B H14D 0.9700 . ?
C14B H14E 0.9700 . ?
C14B H14F 0.9700 . ?
C15B H15D 0.9700 . ?
C15B H15E 0.9700 . ?
C15B H15F 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
O1 C1 O2 122.02(9) . . ?
O1 C1 C2 121.49(9) . . ?
O2 C1 C2 116.49(9) . . ?
C5 C2 C1 119.18(9) . . ?
C5 C2 C3 126.74(9) . . ?
C1 C2 C3 114.08(9) . . ?
C2 C3 C4 112.77(8) . . ?
C2 C3 H3A 109.0 . . ?
C4 C3 H3A 109.0 . . ?
C2 C3 H3B 109.0 . . ?
C4 C3 H3B 109.0 . . ?
H3A C3 H3B 107.8 . . ?
O3 C4 O5 123.56(11) . . ?
O3 C4 C3 125.60(10) . . ?
O5 C4 C3 110.83(9) . . ?
C2 C5 C6 130.72(10) . . ?
C2 C5 H5 114.6 . . ?
C6 C5 H5 114.6 . . ?
C7 C6 C11 116.81(10) . . ?
C7 C6 C5 117.81(9) . . ?
C11 C6 C5 125.38(9) . . ?
C8 C7 C6 122.66(10) . . ?
C8 C7 H7 118.7 . . ?
C6 C7 H7 118.7 . . ?
C7 C8 C9 119.13(10) . . ?
C7 C8 H8 120.4 . . ?
C9 C8 H8 120.4 . . ?
O4 C9 C8 124.72(10) . . ?
O4 C9 C10 115.90(10) . . ?
C8 C9 C10 119.39(10) . . ?
C11 C10 C9 120.98(10) . . ?
C11 C10 H10 119.5 . . ?
C9 C10 H10 119.5 . . ?
C10 C11 C6 120.99(10) . . ?
C10 C11 H11 119.5 . . ?
C6 C11 H11 119.5 . . ?
O4 C12 H12A 109.5 . . ?
O4 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
O4 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C1 O2 H2 109.5 . . ?
C9 O4 C12 117.46(10) . . ?
C4 O5 C13B 118.5(5) . . ?
C4 O5 C13A 116.7(5) . . ?
O5 C13A C15A 102.4(9) . . ?
O5 C13A C14A 112.1(10) . . ?
C15A C13A C14A 109.2(9) . . ?
O5 C13A H13A 110.9 . . ?
C15A C13A H13A 110.9 . . ?
C14A C13A H13A 110.9 . . ?
C13A C14A H14A 109.5 . . ?
C13A C14A H14B 109.5 . . ?
H14A C14A H14B 109.5 . . ?
C13A C14A H14C 109.5 . . ?
H14A C14A H14C 109.5 . . ?
H14B C14A H14C 109.5 . . ?
C13A C15A H15A 109.5 . . ?
C13A C15A H15B 109.5 . . ?
H15A C15A H15B 109.5 . . ?
C13A C15A H15C 109.5 . . ?
H15A C15A H15C 109.5 . . ?
H15B C15A H15C 109.5 . . ?
C15B C13B O5 108.7(7) . . ?
C15B C13B C14B 116.7(9) . . ?
O5 C13B C14B 102.4(8) . . ?
C15B C13B H13B 109.6 . . ?
O5 C13B H13B 109.6 . . ?
C14B C13B H13B 109.6 . . ?
C13B C14B H14D 109.5 . . ?
C13B C14B H14E 109.5 . . ?
H14D C14B H14E 109.5 . . ?
C13B C14B H14F 109.5 . . ?
H14D C14B H14F 109.5 . . ?
H14E C14B H14F 109.5 . . ?
C13B C15B H15D 109.5 . . ?
C13B C15B H15E 109.5 . . ?
H15D C15B H15E 109.5 . . ?
C13B C15B H15F 109.5 . . ?
H15D C15B H15F 109.5 . . ?
H15E C15B H15F 109.5 . . ?

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 C5 -178.97(10) . . . . ?
O2 C1 C2 C5 0.69(14) . . . . ?
O1 C1 C2 C3 0.38(14) . . . . ?
O2 C1 C2 C3 -179.96(8) . . . . ?
C5 C2 C3 C4 -95.01(12) . . . . ?
C1 C2 C3 C4 85.69(11) . . . . ?
C2 C3 C4 O3 1.70(17) . . . . ?
C2 C3 C4 O5 -177.20(9) . . . . ?
C1 C2 C5 C6 179.07(10) . . . . ?
C3 C2 C5 C6 -0.19(18) . . . . ?
C2 C5 C6 C7 -158.66(11) . . . . ?
C2 C5 C6 C11 21.40(18) . . . . ?
C11 C6 C7 C8 -1.64(17) . . . . ?
C5 C6 C7 C8 178.41(10) . . . . ?
C6 C7 C8 C9 0.57(19) . . . . ?
C7 C8 C9 O4 -179.90(11) . . . . ?
C7 C8 C9 C10 0.31(19) . . . . ?
O4 C9 C10 C11 -179.85(12) . . . . ?
C8 C9 C10 C11 0.0(2) . . . . ?
C9 C10 C11 C6 -1.1(2) . . . . ?
C7 C6 C11 C10 1.89(18) . . . . ?
C5 C6 C11 C10 -178.17(11) . . . . ?
C8 C9 O4 C12 -1.14(19) . . . . ?
C10 C9 O4 C12 178.66(12) . . . . ?
O3 C4 O5 C13B -2.5(6) . . . . ?
C3 C4 O5 C13B 176.4(5) . . . . ?
O3 C4 O5 C13A 10.9(7) . . . . ?
C3 C4 O5 C13A -170.2(7) . . . . ?
C4 O5 C13A C15A -107.5(6) . . . . ?
C4 O5 C13A C14A 135.5(6) . . . . ?
C4 O5 C13B C15B -148.0(6) . . . . ?
C4 O5 C13B C14B 87.9(8) . . . . ?

loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O2 H2 O1 0.91 1.75 2.6622(11) 177.1 5_656 yes

_refine_diff_density_max         0.370
_refine_diff_density_min         -0.287
_refine_diff_density_rms         0.041



