#------------------------------------------------------------------------------
#$Date: 2025-08-18 18:33:07 +0300 (Mon, 18 Aug 2025) $
#$Revision: 301779 $
#$URL: file:///home/coder/svn-repositories/cod/cif/1/54/50/1545041.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/. The original data for this entry
# were provided by IUCr Journals, http://journals.iucr.org/.
#
# The file may be used within the scientific community so long as
# proper attribution is given to the journal article from which the
# data were obtained.
#
data_1545041
loop_
_publ_author_name
'Sharmila, N.'
'Sundar, T. V.'
'Sakthivel, P.'
'Venkatesan, P.'
_publ_section_title
;
 Ethyl
 6-(4-chlorophenyl)-2,2-dimethyl-4-oxo-3,4-dihydro-2H-pyran-5-carboxylate
;
_journal_coeditor_code           TK4027
_journal_issue                   1
_journal_name_full               IUCrData
_journal_page_first              x170034
_journal_paper_doi               10.1107/S2414314617000347
_journal_volume                  2
_journal_year                    2017
_chemical_formula_moiety         'C16 H17 Cl O4'
_chemical_formula_sum            'C16 H17 Cl O4'
_chemical_formula_weight         308.74
_chemical_melting_point          356
_chemical_name_common
'Ethyl 2,2-dimethyl-4-oxo-6-phenyl-2,3-dihydro-4H-pyran-5-carboxylate'
_chemical_name_systematic
'Ethyl 2,2-dimethyl-4-oxo-6-phenyl-2,3-dihydro-4H-pyran-5-carboxylate'
_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'
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2014/7
_cell_angle_alpha                90
_cell_angle_beta                 102.311(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.4412(3)
_cell_length_b                   7.6959(2)
_cell_length_c                   20.2651(5)
_cell_measurement_reflns_used    3995
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      28.427
_cell_measurement_theta_min      1.996
_cell_volume                     1590.95(7)
_computing_cell_refinement
;
SAINT (Bruker, 2008)
;
_computing_data_collection
;
SMART (Bruker, 2008)
;
_computing_data_reduction
;
SAINT (Bruker, 2008)
;
_computing_molecular_graphics
;
QMOL (Gans & Shalloway, 2001), Mercury (Macrae et al.,
2008)
and ORTEPIII
(Burnett
& Johnson, 1996)
;
_computing_publication_material
;
WinGX publication routines (Farrugia, 2012) and PLATON (Spek,
2009)
;
_computing_structure_refinement
;
SHELXL-2014 (Sheldrick, 2015)
;
_computing_structure_solution
;
SHELXS97 (Sheldrick, 2008)
;
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker Smart  CCD Area-detector'
_diffrn_measurement_method       'phi and omega scans'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0184
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       10
_diffrn_reflns_limit_k_min       -10
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -24
_diffrn_reflns_number            15125
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         28.427
_diffrn_reflns_theta_min         1.996
_exptl_absorpt_coefficient_mu    0.252
_exptl_absorpt_correction_T_max  0.845
_exptl_absorpt_correction_T_min  0.746
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Bruker, 2008)
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.289
_exptl_crystal_description       block
_exptl_crystal_F_000             648
_exptl_crystal_size_max          0.250
_exptl_crystal_size_mid          0.170
_exptl_crystal_size_min          0.120
_refine_diff_density_max         0.280
_refine_diff_density_min         -0.259
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.026
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     193
_refine_ls_number_reflns         3995
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.026
_refine_ls_R_factor_all          0.0531
_refine_ls_R_factor_gt           0.0369
_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/[σ²(Fo²)+(0.0484P)²+0.3683P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0969
_refine_ls_wR_factor_ref         0.1084
_reflns_number_gt                2978
_reflns_number_total             3995
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            tk4027sup1.cif
_cod_data_source_block           I
_cod_original_cell_volume        1590.94(7)
_cod_database_code               1545041
_cod_database_fobs_code          1545041
_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.
;
_shelx_estimated_absorpt_t_min   0.940
_shelx_estimated_absorpt_t_max   0.970
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -y-1/2, z-1/2'
loop_
_atom_site_type_symbol
_atom_site_label
_atom_site_fract_x
_atom_site_fract_y
_atom_site_fract_z
_atom_site_U_iso_or_equiv
_atom_site_adp_type
_atom_site_calc_flag
_atom_site_occupancy
Cl Cl1 0.43713(4) 0.28175(7) 0.02231(2) 0.06956(16) Uani d 1
O O1 0.76719(10) 0.25784(13) 0.33513(5) 0.0475(2) Uani d 1
O O2 1.03226(13) 0.63993(19) 0.40015(6) 0.0736(4) Uani d 1
O O3 0.96413(11) 0.71077(17) 0.24439(7) 0.0670(3) Uani d 1
O O4 0.76146(10) 0.76716(13) 0.25811(5) 0.0494(3) Uani d 1
C C1 0.56401(14) 0.3304(2) 0.22085(7) 0.0476(3) Uani d 1
H H1 0.5298 0.3190 0.2594 0.057 Uiso calc 1
C C2 0.48338(14) 0.3058(2) 0.15815(7) 0.0515(4) Uani d 1
H H2 0.3950 0.2802 0.1541 0.062 Uiso calc 1
C C3 0.53638(14) 0.3198(2) 0.10154(7) 0.0451(3) Uani d 1
C C4 0.66627(14) 0.3583(2) 0.10654(7) 0.0464(3) Uani d 1
H H4 0.7003 0.3669 0.0678 0.056 Uiso calc 1
C C5 0.74647(13) 0.38433(18) 0.16963(7) 0.0420(3) Uani d 1
H H5 0.8347 0.4102 0.1733 0.050 Uiso calc 1
C C6 0.69542(12) 0.37183(17) 0.22726(6) 0.0368(3) Uani d 1
C C7 0.78238(12) 0.39149(17) 0.29499(6) 0.0374(3) Uani d 1
C C8 0.83024(15) 0.2695(2) 0.40731(7) 0.0498(4) Uani d 1
C C9 0.96580(15) 0.3470(2) 0.41366(7) 0.0524(4) Uani d 1
H H9A 1.0057 0.3629 0.4611 0.063 Uiso calc 1
H H9B 1.0200 0.2667 0.3948 0.063 Uiso calc 1
C C10 0.96159(14) 0.5182(2) 0.37801(7) 0.0486(3) Uani d 1
C C11 0.86698(12) 0.52417(18) 0.31346(6) 0.0391(3) Uani d 1
C C12 0.87223(13) 0.67511(18) 0.26829(7) 0.0415(3) Uani d 1
C C13 0.75166(17) 0.9164(2) 0.21306(9) 0.0601(4) Uani d 1
H H13A 0.8384 0.9637 0.2147 0.072 Uiso calc 1
H H13B 0.6989 1.0060 0.2279 0.072 Uiso calc 1
C C14 0.6913(2) 0.8648(3) 0.14272(10) 0.0745(5) Uani d 1
H H14A 0.7470 0.7826 0.1269 0.112 Uiso calc 1
H H14B 0.6805 0.9657 0.1142 0.112 Uiso calc 1
H H14C 0.6072 0.8128 0.1416 0.112 Uiso calc 1
C C15 0.74350(17) 0.3815(3) 0.44129(8) 0.0685(5) Uani d 1
H H15A 0.7383 0.4966 0.4226 0.103 Uiso calc 1
H H15B 0.7800 0.3869 0.4889 0.103 Uiso calc 1
H H15C 0.6573 0.3319 0.4339 0.103 Uiso calc 1
C C16 0.8362(2) 0.0834(3) 0.43209(10) 0.0813(6) Uani d 1
H H16A 0.7490 0.0372 0.4255 0.122 Uiso calc 1
H H16B 0.8768 0.0801 0.4793 0.122 Uiso calc 1
H H16C 0.8866 0.0149 0.4072 0.122 Uiso calc 1
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'
Cl Cl 0.1484 0.1585 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
loop_
_geom_angle_atom_site_label_1
_geom_angle_atom_site_label_2
_geom_angle_atom_site_label_3
_geom_angle
C7 O1 C8 118.01(11)
C12 O4 C13 117.26(11)
C2 C1 C6 120.99(12)
C2 C1 H1 119.5
C6 C1 H1 119.5
C1 C2 C3 118.74(13)
C1 C2 H2 120.6
C3 C2 H2 120.6
C4 C3 C2 121.41(13)
C4 C3 Cl1 119.33(11)
C2 C3 Cl1 119.24(11)
C3 C4 C5 119.57(12)
C3 C4 H4 120.2
C5 C4 H4 120.2
C4 C5 C6 120.13(12)
C4 C5 H5 119.9
C6 C5 H5 119.9
C5 C6 C1 119.15(12)
C5 C6 C7 120.20(11)
C1 C6 C7 120.54(11)
O1 C7 C11 124.54(11)
O1 C7 C6 110.78(11)
C11 C7 C6 124.68(11)
O1 C8 C16 104.45(13)
O1 C8 C9 108.65(11)
C16 C8 C9 111.84(14)
O1 C8 C15 107.56(12)
C16 C8 C15 111.90(15)
C9 C8 C15 112.02(14)
C10 C9 C8 111.96(12)
C10 C9 H9A 109.2
C8 C9 H9A 109.2
C10 C9 H9B 109.2
C8 C9 H9B 109.2
H9A C9 H9B 107.9
O2 C10 C11 123.09(14)
O2 C10 C9 123.08(13)
C11 C10 C9 113.82(13)
C7 C11 C10 120.09(12)
C7 C11 C12 121.88(11)
C10 C11 C12 117.96(12)
O3 C12 O4 124.04(13)
O3 C12 C11 124.53(13)
O4 C12 C11 111.43(11)
O4 C13 C14 110.47(14)
O4 C13 H13A 109.6
C14 C13 H13A 109.6
O4 C13 H13B 109.6
C14 C13 H13B 109.6
H13A C13 H13B 108.1
C13 C14 H14A 109.5
C13 C14 H14B 109.5
H14A C14 H14B 109.5
C13 C14 H14C 109.5
H14A C14 H14C 109.5
H14B C14 H14C 109.5
C8 C15 H15A 109.5
C8 C15 H15B 109.5
H15A C15 H15B 109.5
C8 C15 H15C 109.5
H15A C15 H15C 109.5
H15B C15 H15C 109.5
C8 C16 H16A 109.5
C8 C16 H16B 109.5
H16A C16 H16B 109.5
C8 C16 H16C 109.5
H16A C16 H16C 109.5
H16B C16 H16C 109.5
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_distance
Cl1 C3 1.7401(13)
O1 C7 1.3415(16)
O1 C8 1.4732(16)
O2 C10 1.2177(19)
O3 C12 1.1954(17)
O4 C12 1.3343(17)
O4 C13 1.4571(18)
C1 C2 1.3795(19)
C1 C6 1.3876(19)
C1 H1 0.9300
C2 C3 1.380(2)
C2 H2 0.9300
C3 C4 1.371(2)
C4 C5 1.3854(18)
C4 H4 0.9300
C5 C6 1.3866(18)
C5 H5 0.9300
C6 C7 1.4832(16)
C7 C11 1.3498(18)
C8 C16 1.515(2)
C8 C9 1.516(2)
C8 C15 1.518(2)
C9 C10 1.498(2)
C9 H9A 0.9700
C9 H9B 0.9700
C10 C11 1.4622(18)
C11 C12 1.4871(19)
C13 C14 1.484(3)
C13 H13A 0.9700
C13 H13B 0.9700
C14 H14A 0.9600
C14 H14B 0.9600
C14 H14C 0.9600
C15 H15A 0.9600
C15 H15B 0.9600
C15 H15C 0.9600
C16 H16A 0.9600
C16 H16B 0.9600
C16 H16C 0.9600
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_site_symmetry_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
C2 H2 O4 2_645 0.93 2.66 3.3694(18) 134
C15 H15B O2 3_766 0.96 2.66 3.553(2) 156
C13 H13B Cg 1_565 0.97 2.96 3.6463(17) 129
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
C6 C1 C2 C3 1.2(2)
C1 C2 C3 C4 -0.4(2)
C1 C2 C3 Cl1 177.82(13)
C2 C3 C4 C5 -0.2(2)
Cl1 C3 C4 C5 -178.35(12)
C3 C4 C5 C6 -0.2(2)
C4 C5 C6 C1 1.0(2)
C4 C5 C6 C7 177.14(13)
C2 C1 C6 C5 -1.6(2)
C2 C1 C6 C7 -177.69(14)
C8 O1 C7 C11 10.50(19)
C8 O1 C7 C6 -170.55(11)
C5 C6 C7 O1 -128.38(13)
C1 C6 C7 O1 47.68(17)
C5 C6 C7 C11 50.56(19)
C1 C6 C7 C11 -133.37(15)
C7 O1 C8 C16 -160.72(14)
C7 O1 C8 C9 -41.22(17)
C7 O1 C8 C15 80.23(16)
O1 C8 C9 C10 54.88(17)
C16 C8 C9 C10 169.65(14)
C15 C8 C9 C10 -63.80(16)
C8 C9 C10 O2 141.88(16)
C8 C9 C10 C11 -39.47(18)
O1 C7 C11 C10 7.7(2)
C6 C7 C11 C10 -171.07(12)
O1 C7 C11 C12 -175.43(12)
C6 C7 C11 C12 5.8(2)
O2 C10 C11 C7 -173.28(15)
C9 C10 C11 C7 8.07(19)
O2 C10 C11 C12 9.8(2)
C9 C10 C11 C12 -168.88(13)
C13 O4 C12 O3 2.3(2)
C13 O4 C12 C11 -178.24(12)
C7 C11 C12 O3 -115.07(17)
C10 C11 C12 O3 61.8(2)
C7 C11 C12 O4 65.43(17)
C10 C11 C12 O4 -117.67(13)
C12 O4 C13 C14 91.59(17)
loop_
_cod_related_entry_id
_cod_related_entry_database
_cod_related_entry_code
1 PubChem 139049503
