#------------------------------------------------------------------------------
#$Date: 2022-02-09 00:54:45 +0200 (Wed, 09 Feb 2022) $
#$Revision: 272857 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/12/96/7129688.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_7129688
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_absolute_configuration syn
_chemical_formula_moiety         'C21 H24 O3'
_chemical_formula_sum            'C21 H24 O3'
_chemical_formula_weight         324.40
_space_group_crystal_system      monoclinic
_space_group_IT_number           4
_space_group_name_Hall           'P 2yb'
_space_group_name_H-M_alt        'P 1 21 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2020-12-29 deposited with the CCDC.	2022-02-04 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 94.723(12)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   6.549(3)
_cell_length_b                   12.882(5)
_cell_length_c                   10.906(5)
_cell_measurement_reflns_used    9297
_cell_measurement_temperature    294(2)
_cell_measurement_theta_max      56.73
_cell_measurement_theta_min      2.56
_cell_volume                     917.0(7)
_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  'SHELXL2014 (Sheldrick, 2015)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      294(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.993
_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  0.0612
_diffrn_reflns_av_unetI/netI     0.0445
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -8
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            33298
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.989
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.541
_diffrn_reflns_theta_min         2.452
_exptl_absorpt_coefficient_mu    0.077
_exptl_absorpt_correction_T_max  0.7461
_exptl_absorpt_correction_T_min  0.6801
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS, Bruker, 2016'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.175
_exptl_crystal_description       block
_exptl_crystal_F_000             348
_exptl_crystal_size_max          0.280
_exptl_crystal_size_mid          0.260
_exptl_crystal_size_min          0.180
_refine_diff_density_max         0.209
_refine_diff_density_min         -0.197
_refine_diff_density_rms         0.042
_refine_ls_abs_structure_details
;
 Flack x determined using 1545 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.2(4)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.031
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     222
_refine_ls_number_reflns         5572
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.031
_refine_ls_R_factor_all          0.0812
_refine_ls_R_factor_gt           0.0518
_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)+(0.0719P)²+0.0917P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1239
_refine_ls_wR_factor_ref         0.1401
_reflns_Friedel_coverage         0.914
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.985
_reflns_number_gt                4019
_reflns_number_total             5572
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d1cc06810e2.cif
_cod_data_source_block           KA845_0m
_cod_original_cell_volume        916.9(7)
_cod_original_sg_symbol_H-M      'P 21'
_cod_database_code               7129688
_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   0.979
_shelx_estimated_absorpt_t_max   0.986
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -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 0.1913(3) 0.48766(16) 0.5563(2) 0.0317(4) Uani 1 1 d . . . . .
C2 C 0.0966(4) 0.46208(19) 0.4286(2) 0.0398(5) Uani 1 1 d . . . . .
H2A H 0.018692 0.398038 0.428472 0.048 Uiso 1 1 calc R U . . .
H2B H 0.200474 0.456058 0.370510 0.048 Uiso 1 1 calc R U . . .
C3 C -0.0447(4) 0.5564(2) 0.3982(2) 0.0418(5) Uani 1 1 d . . . . .
H3 H 0.041851 0.611210 0.367861 0.050 Uiso 1 1 calc R U . . .
C4 C -0.1075(4) 0.5929(2) 0.5237(2) 0.0399(5) Uani 1 1 d . . . . .
H4A H -0.128804 0.667392 0.524792 0.048 Uiso 1 1 calc R U . . .
H4B H -0.231171 0.558217 0.545060 0.048 Uiso 1 1 calc R U . . .
C5 C 0.0752(3) 0.56166(16) 0.6094(2) 0.0326(4) Uani 1 1 d . . . . .
C6 C 0.1266(3) 0.60042(17) 0.7288(2) 0.0348(5) Uani 1 1 d . . . . .
C7 C 0.3065(3) 0.56487(17) 0.7904(2) 0.0339(4) Uani 1 1 d . . . . .
C8 C 0.4326(3) 0.48887(17) 0.7393(2) 0.0334(5) Uani 1 1 d . . . . .
C9 C 0.3717(3) 0.44701(15) 0.6209(2) 0.0318(4) Uani 1 1 d . . . . .
C10 C 0.6192(4) 0.45405(18) 0.8035(2) 0.0403(5) Uani 1 1 d . . . . .
H10 H 0.660010 0.482022 0.880235 0.048 Uiso 1 1 calc R U . . .
C11 C 0.7387(4) 0.38047(19) 0.7543(3) 0.0448(6) Uani 1 1 d . . . . .
C12 C 0.6760(4) 0.3365(2) 0.6391(3) 0.0458(6) Uani 1 1 d . . . . .
H12 H 0.756312 0.285482 0.606534 0.055 Uiso 1 1 calc R U . . .
C13 C 0.4980(4) 0.36772(16) 0.5739(2) 0.0384(5) Uani 1 1 d . . . . .
C14 C -0.2143(5) 0.5366(2) 0.2975(2) 0.0525(7) Uani 1 1 d . . . . .
C15 C -0.4084(5) 0.5564(4) 0.3096(3) 0.0864(13) Uani 1 1 d . . . . .
H15A H -0.505893 0.544685 0.244118 0.104 Uiso 1 1 calc R U . . .
H15B H -0.448385 0.582103 0.383627 0.104 Uiso 1 1 calc R U . . .
C16 C -0.1436(8) 0.4951(4) 0.1797(3) 0.0908(13) Uani 1 1 d . . . . .
H16A H -0.257661 0.491916 0.118567 0.136 Uiso 1 1 calc R U . . .
H16B H -0.087786 0.426832 0.193442 0.136 Uiso 1 1 calc R U . . .
H16C H -0.040275 0.540118 0.151640 0.136 Uiso 1 1 calc R U . . .
C17 C -0.0094(4) 0.6793(2) 0.7846(3) 0.0503(6) Uani 1 1 d . . . . .
H17A H -0.028292 0.737978 0.730646 0.075 Uiso 1 1 calc R U . . .
H17B H 0.053733 0.701533 0.862764 0.075 Uiso 1 1 calc R U . . .
H17C H -0.139953 0.648392 0.795840 0.075 Uiso 1 1 calc R U . . .
C18 C 0.3712(4) 0.6075(2) 0.9156(2) 0.0445(6) Uani 1 1 d . . . . .
C19 C 0.5661(7) 0.7396(4) 1.0220(4) 0.0881(13) Uani 1 1 d . . . . .
H19A H 0.640347 0.801173 1.003737 0.132 Uiso 1 1 calc R U . . .
H19B H 0.654788 0.693345 1.070531 0.132 Uiso 1 1 calc R U . . .
H19C H 0.451581 0.757990 1.067212 0.132 Uiso 1 1 calc R U . . .
C20 C 0.9355(5) 0.3423(3) 0.8231(3) 0.0647(9) Uani 1 1 d . . . . .
H20A H 1.047289 0.351111 0.772398 0.097 Uiso 1 1 calc R U . . .
H20B H 0.921841 0.270135 0.842871 0.097 Uiso 1 1 calc R U . . .
H20C H 0.961789 0.381513 0.897613 0.097 Uiso 1 1 calc R U . . .
C21 C 0.5573(5) 0.2604(2) 0.4019(3) 0.0595(8) Uani 1 1 d . . . . .
H21A H 0.493798 0.243707 0.321879 0.089 Uiso 1 1 calc R U . . .
H21B H 0.580942 0.197843 0.448696 0.089 Uiso 1 1 calc R U . . .
H21C H 0.685520 0.294758 0.393517 0.089 Uiso 1 1 calc R U . . .
O1 O 0.4928(4) 0.68871(16) 0.90831(18) 0.0594(6) Uani 1 1 d . . . . .
O2 O 0.3208(5) 0.5742(3) 1.0103(2) 0.1063(12) Uani 1 1 d . . . . .
O3 O 0.4260(3) 0.32733(15) 0.46380(18) 0.0519(5) 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
C5 C1 C9 120.70(19) . . ?
C5 C1 C2 109.84(19) . . ?
C9 C1 C2 129.5(2) . . ?
C1 C2 C3 102.64(19) . . ?
C1 C2 H2A 111.2 . . ?
C3 C2 H2A 111.2 . . ?
C1 C2 H2B 111.2 . . ?
C3 C2 H2B 111.2 . . ?
H2A C2 H2B 109.2 . . ?
C14 C3 C4 117.6(2) . . ?
C14 C3 C2 114.4(2) . . ?
C4 C3 C2 104.42(19) . . ?
C14 C3 H3 106.6 . . ?
C4 C3 H3 106.6 . . ?
C2 C3 H3 106.6 . . ?
C5 C4 C3 102.32(19) . . ?
C5 C4 H4A 111.3 . . ?
C3 C4 H4A 111.3 . . ?
C5 C4 H4B 111.3 . . ?
C3 C4 H4B 111.3 . . ?
H4A C4 H4B 109.2 . . ?
C1 C5 C6 122.42(19) . . ?
C1 C5 C4 111.15(19) . . ?
C6 C5 C4 126.4(2) . . ?
C7 C6 C5 117.4(2) . . ?
C7 C6 C17 122.2(2) . . ?
C5 C6 C17 120.4(2) . . ?
C6 C7 C8 122.33(19) . . ?
C6 C7 C18 119.1(2) . . ?
C8 C7 C18 118.61(19) . . ?
C7 C8 C9 119.14(18) . . ?
C7 C8 C10 121.6(2) . . ?
C9 C8 C10 119.3(2) . . ?
C1 C9 C8 117.89(18) . . ?
C1 C9 C13 124.3(2) . . ?
C8 C9 C13 117.82(19) . . ?
C11 C10 C8 121.3(2) . . ?
C11 C10 H10 119.3 . . ?
C8 C10 H10 119.3 . . ?
C10 C11 C12 119.6(2) . . ?
C10 C11 C20 121.4(3) . . ?
C12 C11 C20 118.9(3) . . ?
C13 C12 C11 121.1(2) . . ?
C13 C12 H12 119.5 . . ?
C11 C12 H12 119.5 . . ?
O3 C13 C12 124.3(2) . . ?
O3 C13 C9 114.9(2) . . ?
C12 C13 C9 120.8(2) . . ?
C15 C14 C16 121.6(3) . . ?
C15 C14 C3 123.4(3) . . ?
C16 C14 C3 114.9(3) . . ?
C14 C15 H15A 120.0 . . ?
C14 C15 H15B 120.0 . . ?
H15A C15 H15B 120.0 . . ?
C14 C16 H16A 109.5 . . ?
C14 C16 H16B 109.5 . . ?
H16A C16 H16B 109.5 . . ?
C14 C16 H16C 109.5 . . ?
H16A C16 H16C 109.5 . . ?
H16B C16 H16C 109.5 . . ?
C6 C17 H17A 109.5 . . ?
C6 C17 H17B 109.5 . . ?
H17A C17 H17B 109.5 . . ?
C6 C17 H17C 109.5 . . ?
H17A C17 H17C 109.5 . . ?
H17B C17 H17C 109.5 . . ?
O2 C18 O1 123.3(3) . . ?
O2 C18 C7 125.4(3) . . ?
O1 C18 C7 111.2(2) . . ?
O1 C19 H19A 109.5 . . ?
O1 C19 H19B 109.5 . . ?
H19A C19 H19B 109.5 . . ?
O1 C19 H19C 109.5 . . ?
H19A C19 H19C 109.5 . . ?
H19B C19 H19C 109.5 . . ?
C11 C20 H20A 109.5 . . ?
C11 C20 H20B 109.5 . . ?
H20A C20 H20B 109.5 . . ?
C11 C20 H20C 109.5 . . ?
H20A C20 H20C 109.5 . . ?
H20B C20 H20C 109.5 . . ?
O3 C21 H21A 109.5 . . ?
O3 C21 H21B 109.5 . . ?
H21A C21 H21B 109.5 . . ?
O3 C21 H21C 109.5 . . ?
H21A C21 H21C 109.5 . . ?
H21B C21 H21C 109.5 . . ?
C18 O1 C19 117.7(3) . . ?
C13 O3 C21 118.1(2) . . ?
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 C5 1.376(3) . ?
C1 C9 1.425(3) . ?
C1 C2 1.513(3) . ?
C2 C3 1.547(3) . ?
C2 H2A 0.9700 . ?
C2 H2B 0.9700 . ?
C3 C14 1.518(3) . ?
C3 C4 1.535(4) . ?
C3 H3 0.9800 . ?
C4 C5 1.511(3) . ?
C4 H4A 0.9700 . ?
C4 H4B 0.9700 . ?
C5 C6 1.410(3) . ?
C6 C7 1.385(3) . ?
C6 C17 1.511(3) . ?
C7 C8 1.424(3) . ?
C7 C18 1.500(3) . ?
C8 C9 1.425(3) . ?
C8 C10 1.430(3) . ?
C9 C13 1.435(3) . ?
C10 C11 1.367(4) . ?
C10 H10 0.9300 . ?
C11 C12 1.409(4) . ?
C11 C20 1.519(4) . ?
C12 C13 1.375(4) . ?
C12 H12 0.9300 . ?
C13 O3 1.357(3) . ?
C14 C15 1.314(5) . ?
C14 C16 1.499(5) . ?
C15 H15A 0.9300 . ?
C15 H15B 0.9300 . ?
C16 H16A 0.9600 . ?
C16 H16B 0.9600 . ?
C16 H16C 0.9600 . ?
C17 H17A 0.9600 . ?
C17 H17B 0.9600 . ?
C17 H17C 0.9600 . ?
C18 O2 1.190(4) . ?
C18 O1 1.321(3) . ?
C19 O1 1.449(4) . ?
C19 H19A 0.9600 . ?
C19 H19B 0.9600 . ?
C19 H19C 0.9600 . ?
C20 H20A 0.9600 . ?
C20 H20B 0.9600 . ?
C20 H20C 0.9600 . ?
C21 O3 1.426(3) . ?
C21 H21A 0.9600 . ?
C21 H21B 0.9600 . ?
C21 H21C 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
C5 C1 C2 C3 18.7(2) . . . . ?
C9 C1 C2 C3 -161.2(2) . . . . ?
C1 C2 C3 C14 -159.4(2) . . . . ?
C1 C2 C3 C4 -29.5(2) . . . . ?
C14 C3 C4 C5 157.3(2) . . . . ?
C2 C3 C4 C5 29.4(2) . . . . ?
C9 C1 C5 C6 -0.3(3) . . . . ?
C2 C1 C5 C6 179.8(2) . . . . ?
C9 C1 C5 C4 179.9(2) . . . . ?
C2 C1 C5 C4 0.1(3) . . . . ?
C3 C4 C5 C1 -18.9(3) . . . . ?
C3 C4 C5 C6 161.3(2) . . . . ?
C1 C5 C6 C7 3.1(3) . . . . ?
C4 C5 C6 C7 -177.2(2) . . . . ?
C1 C5 C6 C17 -178.1(2) . . . . ?
C4 C5 C6 C17 1.6(4) . . . . ?
C5 C6 C7 C8 -2.7(3) . . . . ?
C17 C6 C7 C8 178.6(2) . . . . ?
C5 C6 C7 C18 177.5(2) . . . . ?
C17 C6 C7 C18 -1.3(4) . . . . ?
C6 C7 C8 C9 -0.5(3) . . . . ?
C18 C7 C8 C9 179.4(2) . . . . ?
C6 C7 C8 C10 179.2(2) . . . . ?
C18 C7 C8 C10 -1.0(3) . . . . ?
C5 C1 C9 C8 -2.9(3) . . . . ?
C2 C1 C9 C8 176.9(2) . . . . ?
C5 C1 C9 C13 178.1(2) . . . . ?
C2 C1 C9 C13 -2.1(4) . . . . ?
C7 C8 C9 C1 3.2(3) . . . . ?
C10 C8 C9 C1 -176.4(2) . . . . ?
C7 C8 C9 C13 -177.7(2) . . . . ?
C10 C8 C9 C13 2.7(3) . . . . ?
C7 C8 C10 C11 179.5(2) . . . . ?
C9 C8 C10 C11 -0.9(3) . . . . ?
C8 C10 C11 C12 -1.1(4) . . . . ?
C8 C10 C11 C20 -179.2(2) . . . . ?
C10 C11 C12 C13 1.2(4) . . . . ?
C20 C11 C12 C13 179.3(3) . . . . ?
C11 C12 C13 O3 -178.5(2) . . . . ?
C11 C12 C13 C9 0.7(4) . . . . ?
C1 C9 C13 O3 -4.3(3) . . . . ?
C8 C9 C13 O3 176.7(2) . . . . ?
C1 C9 C13 C12 176.4(2) . . . . ?
C8 C9 C13 C12 -2.6(3) . . . . ?
C4 C3 C14 C15 5.2(5) . . . . ?
C2 C3 C14 C15 128.2(4) . . . . ?
C4 C3 C14 C16 -176.5(3) . . . . ?
C2 C3 C14 C16 -53.5(4) . . . . ?
C6 C7 C18 O2 87.9(4) . . . . ?
C8 C7 C18 O2 -92.0(4) . . . . ?
C6 C7 C18 O1 -91.9(3) . . . . ?
C8 C7 C18 O1 88.3(3) . . . . ?
O2 C18 O1 C19 -0.6(5) . . . . ?
C7 C18 O1 C19 179.1(3) . . . . ?
C12 C13 O3 C21 -10.5(4) . . . . ?
C9 C13 O3 C21 170.3(2) . . . . ?
