#------------------------------------------------------------------------------
#$Date: 2021-12-02 04:18:58 +0200 (Thu, 02 Dec 2021) $
#$Revision: 270974 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/39/7243985.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_7243985
loop_
_publ_author_name
'Anwar, Shaik'
'Lin, Li-Tzu'
'Srinivasadesikan, V.'
'Gudise, Veera Babu'
'Chen, Kwunmin'
_publ_section_title
;
 [3+2] regioselective annulation reaction of 2-arylidene-1,3-indandiones
 towards synthesis of spirocyclopentenes: understanding the mechanism of
 γ-attack vs. α-attack using DFT studies
;
_journal_issue                   61
_journal_name_full               'RSC Advances'
_journal_page_first              38648
_journal_page_last               38653
_journal_paper_doi               10.1039/D1RA07165C
_journal_volume                  11
_journal_year                    2021
_chemical_formula_moiety         'C22 H17 Cl O4'
_chemical_formula_sum            'C22 H17 Cl O4'
_chemical_formula_weight         380.81
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_symmetry_cell_setting           monoclinic
_symmetry_space_group_name_H-M   'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-97
_audit_update_record
;
2021-09-17 deposited with the CCDC.	2021-11-19 downloaded from the CCDC.
;
_cell_angle_alpha                90.00
_cell_angle_beta                 111.044(6)
_cell_angle_gamma                90.00
_cell_formula_units_Z            4
_cell_length_a                   18.038(4)
_cell_length_b                   5.5757(14)
_cell_length_c                   19.590(5)
_cell_measurement_reflns_used    1728
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      24.73
_cell_measurement_theta_min      3.11
_cell_volume                     1838.8(8)
_computing_molecular_graphics    'Ortep-3 for Windows (Farrugia, 1997)'
_computing_publication_material  'WinGX publication routines (Farrugia, 1999)'
_computing_structure_refinement  'SHELXL-97 (Sheldrick, 1997)'
_computing_structure_solution    'SHELXS-86 (Sheldrick, 1986)'
_diffrn_ambient_temperature      200(2)
_diffrn_measured_fraction_theta_full 0.981
_diffrn_measured_fraction_theta_max 0.981
_diffrn_measurement_device_type  'Bruker APEX2'
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_source         'fine-focus sealed tube'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0684
_diffrn_reflns_av_sigmaI/netI    0.1073
_diffrn_reflns_limit_h_max       20
_diffrn_reflns_limit_h_min       -21
_diffrn_reflns_limit_k_max       6
_diffrn_reflns_limit_k_min       -6
_diffrn_reflns_limit_l_max       23
_diffrn_reflns_limit_l_min       -23
_diffrn_reflns_number            11954
_diffrn_reflns_theta_full        25.09
_diffrn_reflns_theta_max         25.09
_diffrn_reflns_theta_min         1.32
_exptl_absorpt_coefficient_mu    0.233
_exptl_absorpt_correction_T_max  0.9977
_exptl_absorpt_correction_T_min  0.8690
_exptl_absorpt_correction_type   multi-scan
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.376
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       prism
_exptl_crystal_F_000             792
_exptl_crystal_size_max          0.62
_exptl_crystal_size_mid          0.06
_exptl_crystal_size_min          0.01
_refine_diff_density_max         0.243
_refine_diff_density_min         -0.264
_refine_diff_density_rms         0.061
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.978
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     244
_refine_ls_number_reflns         3221
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      0.978
_refine_ls_R_factor_all          0.1282
_refine_ls_R_factor_gt           0.0587
_refine_ls_shift/su_max          0.000
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'calc w=1/[σ²(Fo²)+(0.0653P)²+0.0000P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1182
_refine_ls_wR_factor_ref         0.1409
_reflns_number_gt                1833
_reflns_number_total             3221
_reflns_threshold_expression     >2sigma(I)
_cod_data_source_file            d1ra07165c2.cif
_cod_data_source_block           a14859
_cod_original_cell_volume        1838.9(8)
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7243985
loop_
_symmetry_equiv_pos_as_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'
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_symmetry_multiplicity
_atom_site_calc_flag
_atom_site_refinement_flags
_atom_site_disorder_assembly
_atom_site_disorder_group
C1 C 0.65415(18) 0.5857(6) 0.43614(17) 0.0249(8) Uani 1 1 d . . .
C2 C 0.72243(18) 0.5975(6) 0.41098(16) 0.0233(8) Uani 1 1 d . . .
C3 C 0.78429(18) 0.7593(7) 0.42998(17) 0.0314(9) Uani 1 1 d . . .
H3 H 0.7885 0.8828 0.4646 0.038 Uiso 1 1 calc R . .
C4 C 0.8396(2) 0.7358(7) 0.39711(19) 0.0371(10) Uani 1 1 d . . .
H4 H 0.8821 0.8476 0.4083 0.045 Uiso 1 1 calc R . .
C5 C 0.8347(2) 0.5513(7) 0.34775(18) 0.0373(10) Uani 1 1 d . . .
H5 H 0.8737 0.5391 0.3258 0.045 Uiso 1 1 calc R . .
C6 C 0.77359(19) 0.3852(7) 0.33022(17) 0.0324(9) Uani 1 1 d . . .
H6 H 0.7705 0.2575 0.2972 0.039 Uiso 1 1 calc R . .
C7 C 0.71720(18) 0.4114(6) 0.36231(16) 0.0231(8) Uani 1 1 d . . .
C8 C 0.64578(18) 0.2644(7) 0.35318(16) 0.0248(8) Uani 1 1 d . . .
C9 C 0.59597(17) 0.3981(6) 0.38954(16) 0.0233(8) Uani 1 1 d . . .
C10 C 0.52553(17) 0.5475(6) 0.33184(15) 0.0219(8) Uani 1 1 d . . .
H10 H 0.5410 0.7205 0.3349 0.026 Uiso 1 1 calc R . .
C11 C 0.50159(17) 0.4644(6) 0.25317(16) 0.0210(8) Uani 1 1 d . . .
C12 C 0.51772(18) 0.6062(6) 0.20244(17) 0.0274(9) Uani 1 1 d . . .
H12 H 0.5461 0.7519 0.2178 0.033 Uiso 1 1 calc R . .
C13 C 0.4933(2) 0.5400(7) 0.12966(18) 0.0348(10) Uani 1 1 d . . .
H13 H 0.5028 0.6413 0.0947 0.042 Uiso 1 1 calc R . .
C14 C 0.45469(19) 0.3235(7) 0.10895(17) 0.0298(9) Uani 1 1 d . . .
C15 C 0.43793(18) 0.1791(7) 0.15830(17) 0.0289(9) Uani 1 1 d . . .
H15 H 0.4105 0.0319 0.1429 0.035 Uiso 1 1 calc R . .
C16 C 0.46135(17) 0.2498(6) 0.23056(17) 0.0266(9) Uani 1 1 d . . .
H16 H 0.4498 0.1509 0.2650 0.032 Uiso 1 1 calc R . .
C17 C 0.46036(18) 0.5171(6) 0.36220(16) 0.0232(8) Uani 1 1 d . . .
C18 C 0.47666(18) 0.3556(6) 0.41473(17) 0.0268(9) Uani 1 1 d . . .
H18 H 0.4411 0.3135 0.4387 0.032 Uiso 1 1 calc R . .
C19 C 0.55658(17) 0.2466(6) 0.43244(17) 0.0289(9) Uani 1 1 d . . .
H19A H 0.5522 0.0768 0.4167 0.035 Uiso 1 1 calc R . .
H19B H 0.5873 0.2548 0.4856 0.035 Uiso 1 1 calc R . .
C20 C 0.38683(19) 0.6600(7) 0.33060(19) 0.0281(9) Uani 1 1 d . . .
C21 C 0.25602(19) 0.7233(7) 0.3292(2) 0.0421(11) Uani 1 1 d . . .
H21A H 0.2129 0.6143 0.3296 0.051 Uiso 1 1 calc R . .
H21B H 0.2452 0.7718 0.2779 0.051 Uiso 1 1 calc R . .
C22 C 0.2564(2) 0.9380(9) 0.3733(2) 0.0713(15) Uani 1 1 d . . .
H22A H 0.2049 1.0192 0.3530 0.107 Uiso 1 1 calc R . .
H22B H 0.2985 1.0474 0.3723 0.107 Uiso 1 1 calc R . .
H22C H 0.2660 0.8901 0.4239 0.107 Uiso 1 1 calc R . .
O1 O 0.64494(12) 0.7058(5) 0.48388(12) 0.0359(7) Uani 1 1 d . . .
O2 O 0.63038(13) 0.0712(5) 0.32325(12) 0.0340(6) Uani 1 1 d . . .
O3 O 0.37816(13) 0.8117(5) 0.28470(14) 0.0475(8) Uani 1 1 d . . .
O4 O 0.33136(13) 0.5966(5) 0.35699(12) 0.0416(7) Uani 1 1 d . . .
Cl1 Cl 0.42360(6) 0.2318(2) 0.01781(4) 0.0481(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'
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
_geom_angle_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle_publ_flag
O1 C1 C2 126.4(3) . . ?
O1 C1 C9 125.8(3) . . ?
C2 C1 C9 107.8(3) . . ?
C3 C2 C7 121.5(3) . . ?
C3 C2 C1 128.9(3) . . ?
C7 C2 C1 109.6(3) . . ?
C4 C3 C2 117.7(3) . . ?
C4 C3 H3 121.1 . . ?
C2 C3 H3 121.1 . . ?
C3 C4 C5 121.3(3) . . ?
C3 C4 H4 119.4 . . ?
C5 C4 H4 119.4 . . ?
C6 C5 C4 120.9(3) . . ?
C6 C5 H5 119.6 . . ?
C4 C5 H5 119.6 . . ?
C7 C6 C5 117.8(3) . . ?
C7 C6 H6 121.1 . . ?
C5 C6 H6 121.1 . . ?
C6 C7 C2 120.7(3) . . ?
C6 C7 C8 129.5(3) . . ?
C2 C7 C8 109.7(3) . . ?
O2 C8 C7 126.1(3) . . ?
O2 C8 C9 126.1(3) . . ?
C7 C8 C9 107.8(3) . . ?
C8 C9 C1 102.7(3) . . ?
C8 C9 C19 116.9(3) . . ?
C1 C9 C19 113.8(2) . . ?
C8 C9 C10 112.1(2) . . ?
C1 C9 C10 105.4(3) . . ?
C19 C9 C10 105.5(2) . . ?
C17 C10 C11 112.9(2) . . ?
C17 C10 C9 101.4(2) . . ?
C11 C10 C9 115.1(3) . . ?
C17 C10 H10 109.1 . . ?
C11 C10 H10 109.1 . . ?
C9 C10 H10 109.1 . . ?
C12 C11 C16 119.0(3) . . ?
C12 C11 C10 120.0(3) . . ?
C16 C11 C10 120.9(3) . . ?
C11 C12 C13 121.2(3) . . ?
C11 C12 H12 119.4 . . ?
C13 C12 H12 119.4 . . ?
C14 C13 C12 118.5(3) . . ?
C14 C13 H13 120.7 . . ?
C12 C13 H13 120.7 . . ?
C15 C14 C13 121.4(3) . . ?
C15 C14 Cl1 118.5(3) . . ?
C13 C14 Cl1 120.0(3) . . ?
C14 C15 C16 119.4(3) . . ?
C14 C15 H15 120.3 . . ?
C16 C15 H15 120.3 . . ?
C15 C16 C11 120.4(3) . . ?
C15 C16 H16 119.8 . . ?
C11 C16 H16 119.8 . . ?
C18 C17 C20 127.6(3) . . ?
C18 C17 C10 113.5(3) . . ?
C20 C17 C10 118.9(3) . . ?
C17 C18 C19 112.8(3) . . ?
C17 C18 H18 123.6 . . ?
C19 C18 H18 123.6 . . ?
C18 C19 C9 104.4(3) . . ?
C18 C19 H19A 110.9 . . ?
C9 C19 H19A 110.9 . . ?
C18 C19 H19B 110.9 . . ?
C9 C19 H19B 110.9 . . ?
H19A C19 H19B 108.9 . . ?
O3 C20 O4 124.3(3) . . ?
O3 C20 C17 123.2(3) . . ?
O4 C20 C17 112.4(3) . . ?
O4 C21 C22 111.6(3) . . ?
O4 C21 H21A 109.3 . . ?
C22 C21 H21A 109.3 . . ?
O4 C21 H21B 109.3 . . ?
C22 C21 H21B 109.3 . . ?
H21A C21 H21B 108.0 . . ?
C21 C22 H22A 109.5 . . ?
C21 C22 H22B 109.5 . . ?
H22A C22 H22B 109.5 . . ?
C21 C22 H22C 109.5 . . ?
H22A C22 H22C 109.5 . . ?
H22B C22 H22C 109.5 . . ?
C20 O4 C21 117.3(3) . . ?
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 1.209(4) . ?
C1 C2 1.483(4) . ?
C1 C9 1.530(4) . ?
C2 C3 1.378(4) . ?
C2 C7 1.390(4) . ?
C3 C4 1.375(4) . ?
C3 H3 0.9500 . ?
C4 C5 1.393(5) . ?
C4 H4 0.9500 . ?
C5 C6 1.385(5) . ?
C5 H5 0.9500 . ?
C6 C7 1.382(4) . ?
C6 H6 0.9500 . ?
C7 C8 1.482(4) . ?
C8 O2 1.210(4) . ?
C8 C9 1.526(4) . ?
C9 C19 1.534(4) . ?
C9 C10 1.599(4) . ?
C10 C17 1.506(4) . ?
C10 C11 1.516(4) . ?
C10 H10 1.0000 . ?
C11 C12 1.380(4) . ?
C11 C16 1.387(4) . ?
C12 C13 1.383(4) . ?
C12 H12 0.9500 . ?
C13 C14 1.379(5) . ?
C13 H13 0.9500 . ?
C14 C15 1.373(5) . ?
C14 Cl1 1.745(3) . ?
C15 C16 1.381(4) . ?
C15 H15 0.9500 . ?
C16 H16 0.9500 . ?
C17 C18 1.318(4) . ?
C17 C20 1.479(4) . ?
C18 C19 1.486(4) . ?
C18 H18 0.9500 . ?
C19 H19A 0.9900 . ?
C19 H19B 0.9900 . ?
C20 O3 1.203(4) . ?
C20 O4 1.329(4) . ?
C21 O4 1.453(4) . ?
C21 C22 1.476(5) . ?
C21 H21A 0.9900 . ?
C21 H21B 0.9900 . ?
C22 H22A 0.9800 . ?
C22 H22B 0.9800 . ?
C22 H22C 0.9800 . ?
