#------------------------------------------------------------------------------
#$Date: 2022-02-09 00:54:45 +0200 (Wed, 09 Feb 2022) $
#$Revision: 272857 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/96/7129689.cif $
#------------------------------------------------------------------------------
#
# This file is available in the Crystallography Open Database (COD),
# http://www.crystallography.net/
#
# All data on this site have been placed in the public domain by the
# contributors.
#
data_7129689
loop_
_publ_author_name
'Krishna Chaitanya, Nandikolla'
'Sambasiva Rao, Y. N.'
'Choutipalli, Venkata Surya Kumar'
'Mainkar, Prathama S.'
'Subramanian, Venkatesan'
'Chandrasekhar, Srivari'
_publ_section_title
;
 Cascade Aryne Insertion/Vinylogous Aldol Reaction of Vinyl-substituted
 β-Keto/enol Carbonyls
;
_journal_name_full               'Chemical Communications'
_journal_paper_doi               10.1039/D1CC06810E
_journal_year                    2022
_chemical_formula_moiety         'C18 H22 O3'
_chemical_formula_sum            'C18 H22 O3'
_chemical_formula_weight         286.35
_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
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2021-05-21 deposited with the CCDC.	2022-02-04 downloaded from the CCDC.
;
_cell_angle_alpha                95.956(2)
_cell_angle_beta                 104.157(2)
_cell_angle_gamma                100.451(2)
_cell_formula_units_Z            2
_cell_length_a                   8.4785(4)
_cell_length_b                   9.2084(4)
_cell_length_c                   10.5687(5)
_cell_measurement_reflns_used    3438
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      20.92
_cell_measurement_theta_min      2.28
_cell_volume                     777.25(6)
_computing_cell_refinement       'SAINT (Bruker, 2016)'
_computing_data_collection       'APEX3 (Bruker, 2016)'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8 QUEST PHOTON-100'
_diffrn_measurement_method       'ω and φ'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0595
_diffrn_reflns_av_unetI/netI     0.0606
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.998
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       13
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            15804
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.998
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.498
_diffrn_reflns_theta_min         2.536
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  0.7457
_exptl_absorpt_correction_T_min  0.6101
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
 SADABS 2016/2: Krause, L., Herbst-Irmer, R., Sheldrick G.M. & Stalke D.,
 J. Appl. Cryst. 48 (2015) 3-10
;
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.224
_exptl_crystal_description       needle
_exptl_crystal_F_000             308
_exptl_crystal_size_max          0.380
_exptl_crystal_size_mid          0.210
_exptl_crystal_size_min          0.090
_refine_diff_density_max         0.198
_refine_diff_density_min         -0.155
_refine_diff_density_rms         0.037
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.039
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     191
_refine_ls_number_reflns         3555
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.039
_refine_ls_R_factor_all          0.0992
_refine_ls_R_factor_gt           0.0493
_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)+(0.0328P)²+0.1838P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0952
_refine_ls_wR_factor_ref         0.1164
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2134
_reflns_number_total             3555
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1cc06810e2.cif
_cod_data_source_block           KB56_0m
_cod_database_code               7129689
_shelx_shelxl_version_number     2018/3
_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   0.970
_shelx_estimated_absorpt_t_max   0.993
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, -z'
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 0.3011(2) 0.58167(18) 0.66235(16) 0.0356(4) Uani 1 1 d . . . . .
C2 C 0.1843(2) 0.4479(2) 0.61680(18) 0.0465(5) Uani 1 1 d . . . . .
H2 H 0.072279 0.447173 0.607819 0.056 Uiso 1 1 calc R U . . .
C3 C 0.2316(3) 0.3156(2) 0.58448(19) 0.0525(5) Uani 1 1 d . . . . .
H3 H 0.151521 0.227274 0.553621 0.063 Uiso 1 1 calc R U . . .
C4 C 0.3964(3) 0.3146(2) 0.59795(18) 0.0493(5) Uani 1 1 d . . . . .
H4 H 0.428218 0.226173 0.575152 0.059 Uiso 1 1 calc R U . . .
C5 C 0.5144(2) 0.4452(2) 0.64535(16) 0.0427(4) Uani 1 1 d . . . . .
H5 H 0.626151 0.443734 0.655433 0.051 Uiso 1 1 calc R U . . .
C6 C 0.4700(2) 0.57976(18) 0.67860(15) 0.0353(4) Uani 1 1 d . . . . .
C7 C 0.5997(2) 0.7200(2) 0.72916(17) 0.0405(4) Uani 1 1 d . . . . .
C8 C 0.7750(2) 0.7135(2) 0.8016(2) 0.0551(5) Uani 1 1 d . . . . .
H8A H 0.847310 0.734104 0.744406 0.066 Uiso 1 1 calc R U . . .
H8B H 0.776171 0.613166 0.821678 0.066 Uiso 1 1 calc R U . . .
C9 C 0.8436(2) 0.8247(2) 0.9300(2) 0.0546(5) Uani 1 1 d . . . . .
H9A H 0.962842 0.858089 0.944733 0.066 Uiso 1 1 calc R U . . .
H9B H 0.794171 0.911345 0.919996 0.066 Uiso 1 1 calc R U . . .
C10 C 0.8111(2) 0.7618(2) 1.0508(2) 0.0595(6) Uani 1 1 d . . . . .
H10A H 0.859100 0.839489 1.127068 0.071 Uiso 1 1 calc R U . . .
H10B H 0.869304 0.680990 1.064872 0.071 Uiso 1 1 calc R U . . .
C11 C 0.6290(2) 0.7034(2) 1.04497(19) 0.0495(5) Uani 1 1 d . . . . .
H11A H 0.577112 0.633623 0.963763 0.059 Uiso 1 1 calc R U . . .
H11B H 0.624203 0.648547 1.117993 0.059 Uiso 1 1 calc R U . . .
C12 C 0.5292(2) 0.8233(2) 1.05085(19) 0.0515(5) Uani 1 1 d . . . . .
H12A H 0.526479 0.872982 0.973995 0.062 Uiso 1 1 calc R U . . .
H12B H 0.585720 0.897348 1.128536 0.062 Uiso 1 1 calc R U . . .
C13 C 0.3513(3) 0.7652(2) 1.05558(19) 0.0548(5) Uani 1 1 d . . . . .
H13A H 0.303816 0.849896 1.076475 0.066 Uiso 1 1 calc R U . . .
H13B H 0.353927 0.706334 1.126737 0.066 Uiso 1 1 calc R U . . .
C14 C 0.2369(2) 0.6694(2) 0.92761(18) 0.0474(5) Uani 1 1 d . . . . .
H14A H 0.283767 0.584619 0.905917 0.057 Uiso 1 1 calc R U . . .
H14B H 0.129131 0.631193 0.941633 0.057 Uiso 1 1 calc R U . . .
C15 C 0.2137(2) 0.75425(19) 0.81448(18) 0.0414(4) Uani 1 1 d . . . . .
H15 H 0.173790 0.840937 0.826273 0.050 Uiso 1 1 calc R U . . .
C16 C 0.2433(2) 0.72032(17) 0.69897(17) 0.0357(4) Uani 1 1 d . . . . .
C17 C 0.2168(2) 0.8264(2) 0.60261(18) 0.0421(4) Uani 1 1 d . . . . .
C18 C 0.2119(3) 0.8702(3) 0.3860(2) 0.0743(7) Uani 1 1 d . . . . .
H18A H 0.200517 0.815297 0.300808 0.111 Uiso 1 1 calc R U . . .
H18B H 0.308855 0.950087 0.408262 0.111 Uiso 1 1 calc R U . . .
H18C H 0.114972 0.910921 0.384009 0.111 Uiso 1 1 calc R U . . .
O1 O 0.56560(15) 0.84088(14) 0.71342(13) 0.0531(4) Uani 1 1 d . . . . .
O2 O 0.1842(2) 0.94596(15) 0.62565(13) 0.0686(4) Uani 1 1 d . . . . .
O3 O 0.22923(16) 0.77147(13) 0.48392(12) 0.0502(3) Uani 1 1 d . . . . .
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'
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 C1 C6 118.50(15) . . ?
C2 C1 C16 118.93(15) . . ?
C6 C1 C16 122.48(14) . . ?
C3 C2 C1 121.26(18) . . ?
C3 C2 H2 119.4 . . ?
C1 C2 H2 119.4 . . ?
C4 C3 C2 120.07(18) . . ?
C4 C3 H3 120.0 . . ?
C2 C3 H3 120.0 . . ?
C3 C4 C5 119.63(17) . . ?
C3 C4 H4 120.2 . . ?
C5 C4 H4 120.2 . . ?
C4 C5 C6 121.38(18) . . ?
C4 C5 H5 119.3 . . ?
C6 C5 H5 119.3 . . ?
C5 C6 C1 119.12(16) . . ?
C5 C6 C7 120.50(16) . . ?
C1 C6 C7 120.37(15) . . ?
O1 C7 C6 120.47(16) . . ?
O1 C7 C8 119.38(16) . . ?
C6 C7 C8 120.14(16) . . ?
C7 C8 C9 112.85(16) . . ?
C7 C8 H8A 109.0 . . ?
C9 C8 H8A 109.0 . . ?
C7 C8 H8B 109.0 . . ?
C9 C8 H8B 109.0 . . ?
H8A C8 H8B 107.8 . . ?
C10 C9 C8 114.05(17) . . ?
C10 C9 H9A 108.7 . . ?
C8 C9 H9A 108.7 . . ?
C10 C9 H9B 108.7 . . ?
C8 C9 H9B 108.7 . . ?
H9A C9 H9B 107.6 . . ?
C9 C10 C11 116.02(16) . . ?
C9 C10 H10A 108.3 . . ?
C11 C10 H10A 108.3 . . ?
C9 C10 H10B 108.3 . . ?
C11 C10 H10B 108.3 . . ?
H10A C10 H10B 107.4 . . ?
C12 C11 C10 114.46(16) . . ?
C12 C11 H11A 108.6 . . ?
C10 C11 H11A 108.6 . . ?
C12 C11 H11B 108.6 . . ?
C10 C11 H11B 108.6 . . ?
H11A C11 H11B 107.6 . . ?
C11 C12 C13 114.07(16) . . ?
C11 C12 H12A 108.7 . . ?
C13 C12 H12A 108.7 . . ?
C11 C12 H12B 108.7 . . ?
C13 C12 H12B 108.7 . . ?
H12A C12 H12B 107.6 . . ?
C12 C13 C14 114.73(16) . . ?
C12 C13 H13A 108.6 . . ?
C14 C13 H13A 108.6 . . ?
C12 C13 H13B 108.6 . . ?
C14 C13 H13B 108.6 . . ?
H13A C13 H13B 107.6 . . ?
C15 C14 C13 112.62(15) . . ?
C15 C14 H14A 109.1 . . ?
C13 C14 H14A 109.1 . . ?
C15 C14 H14B 109.1 . . ?
C13 C14 H14B 109.1 . . ?
H14A C14 H14B 107.8 . . ?
C16 C15 C14 127.36(16) . . ?
C16 C15 H15 116.3 . . ?
C14 C15 H15 116.3 . . ?
C15 C16 C17 117.52(16) . . ?
C15 C16 C1 122.94(15) . . ?
C17 C16 C1 119.53(15) . . ?
O2 C17 O3 122.99(16) . . ?
O2 C17 C16 124.87(18) . . ?
O3 C17 C16 112.12(15) . . ?
O3 C18 H18A 109.5 . . ?
O3 C18 H18B 109.5 . . ?
H18A C18 H18B 109.5 . . ?
O3 C18 H18C 109.5 . . ?
H18A C18 H18C 109.5 . . ?
H18B C18 H18C 109.5 . . ?
C17 O3 C18 115.62(15) . . ?
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 C2 1.389(2) . ?
C1 C6 1.404(2) . ?
C1 C16 1.496(2) . ?
C2 C3 1.386(2) . ?
C2 H2 0.9300 . ?
C3 C4 1.371(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.375(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.394(2) . ?
C5 H5 0.9300 . ?
C6 C7 1.489(2) . ?
C7 O1 1.217(2) . ?
C7 C8 1.511(2) . ?
C8 C9 1.529(3) . ?
C8 H8A 0.9700 . ?
C8 H8B 0.9700 . ?
C9 C10 1.519(3) . ?
C9 H9A 0.9700 . ?
C9 H9B 0.9700 . ?
C10 C11 1.524(3) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.513(2) . ?
C11 H11A 0.9700 . ?
C11 H11B 0.9700 . ?
C12 C13 1.521(3) . ?
C12 H12A 0.9700 . ?
C12 H12B 0.9700 . ?
C13 C14 1.533(3) . ?
C13 H13A 0.9700 . ?
C13 H13B 0.9700 . ?
C14 C15 1.487(2) . ?
C14 H14A 0.9700 . ?
C14 H14B 0.9700 . ?
C15 C16 1.323(2) . ?
C15 H15 0.9300 . ?
C16 C17 1.489(2) . ?
C17 O2 1.198(2) . ?
C17 O3 1.339(2) . ?
C18 O3 1.445(2) . ?
C18 H18A 0.9600 . ?
C18 H18B 0.9600 . ?
C18 H18C 0.9600 . ?
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
C6 C1 C2 C3 -1.7(3) . . . . ?
C16 C1 C2 C3 -178.47(16) . . . . ?
C1 C2 C3 C4 0.4(3) . . . . ?
C2 C3 C4 C5 0.9(3) . . . . ?
C3 C4 C5 C6 -0.9(3) . . . . ?
C4 C5 C6 C1 -0.4(2) . . . . ?
C4 C5 C6 C7 -179.70(16) . . . . ?
C2 C1 C6 C5 1.7(2) . . . . ?
C16 C1 C6 C5 178.35(15) . . . . ?
C2 C1 C6 C7 -179.05(15) . . . . ?
C16 C1 C6 C7 -2.4(2) . . . . ?
C5 C6 C7 O1 153.09(17) . . . . ?
C1 C6 C7 O1 -26.2(2) . . . . ?
C5 C6 C7 C8 -27.4(2) . . . . ?
C1 C6 C7 C8 153.33(16) . . . . ?
O1 C7 C8 C9 47.1(2) . . . . ?
C6 C7 C8 C9 -132.40(18) . . . . ?
C7 C8 C9 C10 91.0(2) . . . . ?
C8 C9 C10 C11 -58.4(2) . . . . ?
C9 C10 C11 C12 -69.7(2) . . . . ?
C10 C11 C12 C13 -175.56(16) . . . . ?
C11 C12 C13 C14 -69.4(2) . . . . ?
C12 C13 C14 C15 -63.1(2) . . . . ?
C13 C14 C15 C16 124.0(2) . . . . ?
C14 C15 C16 C17 -177.57(16) . . . . ?
C14 C15 C16 C1 2.6(3) . . . . ?
C2 C1 C16 C15 81.6(2) . . . . ?
C6 C1 C16 C15 -95.1(2) . . . . ?
C2 C1 C16 C17 -98.27(19) . . . . ?
C6 C1 C16 C17 85.1(2) . . . . ?
C15 C16 C17 O2 6.6(3) . . . . ?
C1 C16 C17 O2 -173.56(17) . . . . ?
C15 C16 C17 O3 -171.76(15) . . . . ?
C1 C16 C17 O3 8.1(2) . . . . ?
O2 C17 O3 C18 4.1(3) . . . . ?
C16 C17 O3 C18 -177.53(15) . . . . ?
