 
data_YC_3_XL_22_p338_0m_a
_publ_requested_journal          J.Org.Chem.
_publ_contact_author_name        'William H. Hersh'
_publ_contact_author_address     
;Queens College
Department of Chemistry and Biochemistry
65-30 Kissena Blvd.
Queens, NY 11367-1597
;
_publ_contact_author_email       william.hersh@qc.cuny.edu
_publ_contact_author_phone       718-997-4144
loop_
_publ_author_name
_publ_author_address
'Liu, Xiaochen'
;Queens College
Department of Chemistry and Biochemistry
65-30 Kissena Blvd.
Queens, NY 11367-1597
;
'Hong, Dongsub'
;Queens College
Department of Chemistry and Biochemistry
65-30 Kissena Blvd.
Queens, NY 11367-1597
;
'Sapir, Netanel G.'
;Queens College
Department of Chemistry and Biochemistry
65-30 Kissena Blvd.
Queens, NY 11367-1597
;
'Yang, Wen'
;Key Laboratory of Theoretical Chemistry of Environment
Ministry of Education
School of Chemistry and Environment
South China Normal University
Guangzhou 510006
People?s Republic of China
;
'Hersh, William H.'
;Queens College
Department of Chemistry and Biochemistry
65-30 Kissena Blvd.
Queens, NY 11367-1597
;
'Leung, Pak-Hing'
;Division of Chemistry & Biological Chemistry
School of Physical and Mathematical Sciences
Nanyang Technological University
Singapore 637371
Singapore
;
'Yang, Dingqiao'
;Key Laboratory of Theoretical Chemistry of Environment
Ministry of Education
School of Chemistry and Environment
South China Normal University
Guangzhou 510006
People?s Republic of China
;
'Chen, Yu'
;Queens College
Department of Chemistry and Biochemistry
65-30 Kissena Blvd.
Queens, NY 11367-1597
;

_audit_creation_method           SHELXL-2016/6
_chemical_name_systematic        
'methyl (Z)-4-(1-hydroxy-4,4-dimethyl-3-oxopent-1-en-1-yl)benzoate'
_chemical_name_common            ?
_chemical_melting_point          ?
_chemical_formula_moiety         'C15 H18 O4'
_chemical_formula_sum            'C15 H18 O4'
_chemical_formula_weight         262.29

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           14
_space_group_name_H-M_alt        'P 21/n'
_space_group_name_Hall           '-P 2yn'

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

_cell_length_a                   6.1597(5)
_cell_length_b                   21.6415(17)
_cell_length_c                   9.9582(8)
_cell_angle_alpha                90
_cell_angle_beta                 98.7540(10)
_cell_angle_gamma                90
_cell_volume                     1312.02(18)
_cell_formula_units_Z            4
_cell_measurement_temperature    100(2)
_cell_measurement_reflns_used    9163
_cell_measurement_theta_min      2.273
_cell_measurement_theta_max      27.128

_exptl_crystal_description       irregular
_exptl_crystal_colour            'clear colourless'
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    'not measured'
_exptl_crystal_density_diffrn    1.328
_exptl_crystal_F_000             560
_exptl_transmission_factor_min   0.6982
_exptl_transmission_factor_max   0.7455
_exptl_crystal_size_max          0.678
_exptl_crystal_size_mid          0.620
_exptl_crystal_size_min          0.608
_exptl_absorpt_coefficient_mu    0.096
_shelx_estimated_absorpt_T_min   0.938
_shelx_estimated_absorpt_T_max   0.944
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS-2016/2 (Bruker AXS)'
_exptl_special_details           
;
 A crystal obtained by vapor phase diffusion of hexane into an ethyl 
 acetate solution at room temperature was cleaved from a rectangular bar
 and mounted on a 200 micron MiTeGen MicroMount in Paratone-N oil, 
 and then cooled with an Oxford Cryosystems series 700 low-temperature 
 device. A total of 1464 frames were collected and the total exposure 
 time was 2.44 hr.
;
_diffrn_ambient_temperature      100(2)
_diffrn_radiation_wavelength     0.71073
_diffrn_radiation_type           MoK\a
_diffrn_source                   'fine-focus tube'
_diffrn_measurement_device_type  'Bruker Breeze CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_detector_area_resol_mean 8.3333
_diffrn_reflns_number            15047
_diffrn_reflns_av_unetI/netI     0.0131
_diffrn_reflns_av_R_equivalents  0.0204
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_k_min       -27
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_l_min       -12
_diffrn_reflns_limit_l_max       12
_diffrn_reflns_theta_min         1.882
_diffrn_reflns_theta_max         27.101
_diffrn_reflns_theta_full        25.242
_diffrn_measured_fraction_theta_max 1.000
_diffrn_measured_fraction_theta_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_point_group_measured_fraction_full 1.000
_reflns_number_total             2883
_reflns_number_gt                2694
_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       'Bruker Instrument Service v2011.6.0.0'
_computing_cell_refinement       'APEX3 v2017.3-0 (Bruker AXS)'
_computing_data_reduction        'SAINT V8.38A (Bruker AXS, 2017)'
_computing_structure_solution    'SHELXT 2014/5 (Sheldrick, 2014)'
_computing_structure_refinement  'SHELXL-2016/6 (Sheldrick, 2016)'
_computing_molecular_graphics    'shelXle (C. B. Huebschle, rev 833)'
_computing_publication_material  'Mercury 4.1.0 (Build 235322), 2019'
_refine_special_details          
;
 Hydrogen atom positions were calculated and isotropic thermal
 parameters were fixed for all C-H hydrogen atoms. The O-H 
 hydrogen atom was located and the position and isotropic 
 thermal parameter were refined.
;
_refine_ls_structure_factor_coef Fsqd
_refine_ls_matrix_type           full
_refine_ls_weighting_scheme      calc
_refine_ls_weighting_details     
'w=1/[σ²(Fo²)+(0.0470P)²+0.5575P] where P=(Fo²+2Fc²)/3'
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_atom_sites_solution_hydrogens   mixed
_refine_ls_hydrogen_treatment    mixed
_refine_ls_extinction_method     none
_refine_ls_extinction_coef       .
_refine_ls_number_reflns         2883
_refine_ls_number_parameters     180
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0387
_refine_ls_R_factor_gt           0.0362
_refine_ls_wR_factor_ref         0.0942
_refine_ls_wR_factor_gt          0.0921
_refine_ls_goodness_of_fit_ref   1.029
_refine_ls_restrained_S_all      1.029
_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
O1 O 0.11900(12) 0.32542(3) 0.70873(8) 0.01742(18) Uani 1 1 d . . . . .
H1 H 0.065(4) 0.3732(11) 0.619(2) 0.078(7) Uiso 1 1 d . . . . .
O2 O 0.08230(12) 0.40748(4) 0.53883(8) 0.01795(18) Uani 1 1 d . . . . .
O3 O 0.47460(13) 0.60015(4) 0.07353(8) 0.02027(19) Uani 1 1 d . . . . .
O4 O 0.77947(12) 0.54170(3) 0.09002(8) 0.01827(18) Uani 1 1 d . . . . .
C1 C 0.42275(17) 0.25535(5) 0.75134(10) 0.0141(2) Uani 1 1 d . . . . .
C2 C 0.30603(16) 0.31084(5) 0.67892(10) 0.0130(2) Uani 1 1 d . . . . .
C3 C 0.39523(16) 0.34455(5) 0.57732(10) 0.0140(2) Uani 1 1 d . . . . .
H3 H 0.535161 0.333882 0.555222 0.017 Uiso 1 1 calc R U . . .
C4 C 0.27740(16) 0.39289(5) 0.51095(10) 0.0129(2) Uani 1 1 d . . . . .
C5 C 0.67300(18) 0.26186(6) 0.76645(12) 0.0221(2) Uani 1 1 d . . . . .
H5A H 0.718689 0.261117 0.676402 0.033 Uiso 1 1 calc R U . . .
H5B H 0.742593 0.227546 0.821094 0.033 Uiso 1 1 calc R U . . .
H5C H 0.717759 0.301087 0.811520 0.033 Uiso 1 1 calc R U . . .
C6 C 0.35272(18) 0.24793(5) 0.89179(11) 0.0180(2) Uani 1 1 d . . . . .
H6A H 0.192728 0.243452 0.881532 0.027 Uiso 1 1 calc R U . . .
H6B H 0.397881 0.284486 0.947141 0.027 Uiso 1 1 calc R U . . .
H6C H 0.422794 0.211117 0.936438 0.027 Uiso 1 1 calc R U . . .
C7 C 0.3487(2) 0.19832(5) 0.66383(11) 0.0220(2) Uani 1 1 d . . . . .
H7A H 0.189201 0.193510 0.656744 0.033 Uiso 1 1 calc R U . . .
H7B H 0.421677 0.161401 0.706155 0.033 Uiso 1 1 calc R U . . .
H7C H 0.388208 0.203756 0.572870 0.033 Uiso 1 1 calc R U . . .
C8 C 0.35829(16) 0.43252(5) 0.40720(10) 0.0129(2) Uani 1 1 d . . . . .
C9 C 0.23714(16) 0.48519(5) 0.36135(10) 0.0147(2) Uani 1 1 d . . . . .
H9 H 0.103617 0.494047 0.394248 0.018 Uiso 1 1 calc R U . . .
C10 C 0.31135(17) 0.52449(5) 0.26810(10) 0.0151(2) Uani 1 1 d . . . . .
H10 H 0.228882 0.560281 0.237815 0.018 Uiso 1 1 calc R U . . .
C11 C 0.50627(17) 0.51170(5) 0.21865(10) 0.0136(2) Uani 1 1 d . . . . .
C12 C 0.62677(17) 0.45890(5) 0.26300(10) 0.0156(2) Uani 1 1 d . . . . .
H12 H 0.759305 0.449867 0.229110 0.019 Uiso 1 1 calc R U . . .
C13 C 0.55292(17) 0.41968(5) 0.35652(11) 0.0157(2) Uani 1 1 d . . . . .
H13 H 0.635272 0.383806 0.386361 0.019 Uiso 1 1 calc R U . . .
C14 C 0.58064(17) 0.55616(5) 0.11996(10) 0.0145(2) Uani 1 1 d . . . . .
C15 C 0.86921(18) 0.58503(5) 0.00184(11) 0.0194(2) Uani 1 1 d . . . . .
H15A H 1.009760 0.569377 -0.018756 0.029 Uiso 1 1 calc R U . . .
H15B H 0.892207 0.625137 0.047487 0.029 Uiso 1 1 calc R U . . .
H15C H 0.766297 0.589863 -0.082790 0.029 Uiso 1 1 calc R U . . .


_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 C2 1.2724(12) . ?
O1 H1 1.37(2) . ?
O2 C4 1.3125(12) . ?
O2 H1 1.11(2) . ?
O3 C14 1.2062(13) . ?
O4 C14 1.3409(13) . ?
O4 C15 1.4505(12) . ?
C1 C2 1.5237(14) . ?
C1 C5 1.5323(14) . ?
C1 C6 1.5335(14) . ?
C1 C7 1.5393(15) . ?
C2 C3 1.4236(14) . ?
C3 C4 1.3827(14) . ?
C3 H3 0.9500 . ?
C4 C8 1.4859(14) . ?
C5 H5A 0.9800 . ?
C5 H5B 0.9800 . ?
C5 H5C 0.9800 . ?
C6 H6A 0.9800 . ?
C6 H6B 0.9800 . ?
C6 H6C 0.9800 . ?
C7 H7A 0.9800 . ?
C7 H7B 0.9800 . ?
C7 H7C 0.9800 . ?
C8 C13 1.3976(14) . ?
C8 C9 1.4004(14) . ?
C9 C10 1.3869(15) . ?
C9 H9 0.9500 . ?
C10 C11 1.3930(14) . ?
C10 H10 0.9500 . ?
C11 C12 1.3971(14) . ?
C11 C14 1.4961(14) . ?
C12 C13 1.3870(14) . ?
C12 H12 0.9500 . ?
C13 H13 0.9500 . ?
C15 H15A 0.9800 . ?
C15 H15B 0.9800 . ?
C15 H15C 0.9800 . ?

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
C2 O1 H1 100.0(9) . . ?
C4 O2 H1 100.5(11) . . ?
C14 O4 C15 115.39(8) . . ?
C2 C1 C5 111.66(8) . . ?
C2 C1 C6 109.65(8) . . ?
C5 C1 C6 109.78(9) . . ?
C2 C1 C7 106.63(8) . . ?
C5 C1 C7 109.64(9) . . ?
C6 C1 C7 109.40(9) . . ?
O1 C2 C3 119.99(9) . . ?
O1 C2 C1 117.63(9) . . ?
C3 C2 C1 122.34(9) . . ?
C4 C3 C2 119.74(9) . . ?
C4 C3 H3 120.1 . . ?
C2 C3 H3 120.1 . . ?
O2 C4 C3 120.78(9) . . ?
O2 C4 C8 115.02(9) . . ?
C3 C4 C8 124.19(9) . . ?
C1 C5 H5A 109.5 . . ?
C1 C5 H5B 109.5 . . ?
H5A C5 H5B 109.5 . . ?
C1 C5 H5C 109.5 . . ?
H5A C5 H5C 109.5 . . ?
H5B C5 H5C 109.5 . . ?
C1 C6 H6A 109.5 . . ?
C1 C6 H6B 109.5 . . ?
H6A C6 H6B 109.5 . . ?
C1 C6 H6C 109.5 . . ?
H6A C6 H6C 109.5 . . ?
H6B C6 H6C 109.5 . . ?
C1 C7 H7A 109.5 . . ?
C1 C7 H7B 109.5 . . ?
H7A C7 H7B 109.5 . . ?
C1 C7 H7C 109.5 . . ?
H7A C7 H7C 109.5 . . ?
H7B C7 H7C 109.5 . . ?
C13 C8 C9 119.20(9) . . ?
C13 C8 C4 122.22(9) . . ?
C9 C8 C4 118.56(9) . . ?
C10 C9 C8 120.25(9) . . ?
C10 C9 H9 119.9 . . ?
C8 C9 H9 119.9 . . ?
C9 C10 C11 120.30(9) . . ?
C9 C10 H10 119.8 . . ?
C11 C10 H10 119.8 . . ?
C10 C11 C12 119.71(9) . . ?
C10 C11 C14 118.10(9) . . ?
C12 C11 C14 122.18(9) . . ?
C13 C12 C11 120.00(9) . . ?
C13 C12 H12 120.0 . . ?
C11 C12 H12 120.0 . . ?
C12 C13 C8 120.52(9) . . ?
C12 C13 H13 119.7 . . ?
C8 C13 H13 119.7 . . ?
O3 C14 O4 123.96(9) . . ?
O3 C14 C11 123.87(10) . . ?
O4 C14 C11 112.17(9) . . ?
O4 C15 H15A 109.5 . . ?
O4 C15 H15B 109.5 . . ?
H15A C15 H15B 109.5 . . ?
O4 C15 H15C 109.5 . . ?
H15A C15 H15C 109.5 . . ?
H15B C15 H15C 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
C5 C1 C2 O1 -150.42(9) . . . . ?
C6 C1 C2 O1 -28.52(12) . . . . ?
C7 C1 C2 O1 89.83(11) . . . . ?
C5 C1 C2 C3 31.97(13) . . . . ?
C6 C1 C2 C3 153.88(9) . . . . ?
C7 C1 C2 C3 -87.77(11) . . . . ?
O1 C2 C3 C4 -0.31(15) . . . . ?
C1 C2 C3 C4 177.23(9) . . . . ?
C2 C3 C4 O2 -1.15(15) . . . . ?
C2 C3 C4 C8 177.65(9) . . . . ?
O2 C4 C8 C13 -173.77(9) . . . . ?
C3 C4 C8 C13 7.37(15) . . . . ?
O2 C4 C8 C9 7.69(13) . . . . ?
C3 C4 C8 C9 -171.17(9) . . . . ?
C13 C8 C9 C10 -0.83(15) . . . . ?
C4 C8 C9 C10 177.76(9) . . . . ?
C8 C9 C10 C11 0.39(15) . . . . ?
C9 C10 C11 C12 0.24(15) . . . . ?
C9 C10 C11 C14 -179.02(9) . . . . ?
C10 C11 C12 C13 -0.40(15) . . . . ?
C14 C11 C12 C13 178.83(9) . . . . ?
C11 C12 C13 C8 -0.06(16) . . . . ?
C9 C8 C13 C12 0.67(15) . . . . ?
C4 C8 C13 C12 -177.87(9) . . . . ?
C15 O4 C14 O3 3.42(15) . . . . ?
C15 O4 C14 C11 -176.07(8) . . . . ?
C10 C11 C14 O3 -5.27(15) . . . . ?
C12 C11 C14 O3 175.49(10) . . . . ?
C10 C11 C14 O4 174.23(9) . . . . ?
C12 C11 C14 O4 -5.01(14) . . . . ?

_refine_diff_density_max         0.362
_refine_diff_density_min         -0.236
_refine_diff_density_rms         0.047







