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#$Date: 2023-07-01 04:50:37 +0300 (Sat, 01 Jul 2023) $
#$Revision: 284742 $
#$URL: file:///home/coder/svn-repositories/cod/cif/2/02/28/2022806.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_2022806
loop_
_publ_author_name
Vinaya,
'Richard, Austin S.'
'Murthy, Subbiah M.'
'Basavaraju, Yeriyur B.'
'Yathirajan, Hemmige S.'
'Parkin, Sean'
_publ_section_title
;
 The synthesis, crystal structure and spectroscopic analysis of
 (E)-3-(4-chlorophenyl)-1-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)prop-2-en-1-one
;
_journal_coeditor_code           VM2285
_journal_issue                   7
_journal_name_full
'Acta Crystallographica Section E Crystallographic Communications'
_journal_page_first              674
_journal_page_last               677
_journal_paper_doi               10.1107/S2056989023005613
_journal_volume                  79
_journal_year                    2023
_chemical_formula_iupac          'C17 H13 Cl O3'
_chemical_formula_moiety         'C17 H13 Cl O3'
_chemical_formula_sum            'C17 H13 Cl O3'
_chemical_formula_weight         300.72
_chemical_name_systematic
(E)-3-(4-Chlorophenyl)-1-(2,3-dihydrobenzo[b][1,4]dioxin-6-yl)prop-2-en-1-one
_space_group_crystal_system      orthorhombic
_space_group_IT_number           33
_space_group_name_Hall           'P 2c -2n'
_space_group_name_H-M_alt        'P n a 21'
_atom_sites_solution_hydrogens   difmap
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           'SHELXL-2019/2 and CIFFIX'
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   5.8655(5)
_cell_length_b                   14.3499(17)
_cell_length_c                   16.4803(19)
_cell_measurement_reflns_used    9943
_cell_measurement_temperature    200(2)
_cell_measurement_theta_max      27.57
_cell_measurement_theta_min      2.47
_cell_volume                     1387.1(3)
_computing_cell_refinement
;
APEX3 (Bruker, 2016)
;
_computing_data_collection
;
APEX3 (Bruker, 2016)
;
_computing_data_reduction
;
APEX3 (Bruker, 2016)
;
_computing_molecular_graphics
;
Mercury (Macrae et al., 2020)
;
_computing_publication_material
;
SHELX (Sheldrick, 2008) and publCIF (Westrip,
2010)
;
_computing_structure_refinement
;
SHELXL2019 (Sheldrick, 2015b)
;
_computing_structure_solution
;
SHELXT (Sheldrick, 2015a)
;
_diffrn_ambient_temperature      200(2)
_diffrn_detector_area_resol_mean 7.41
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8 Venture dual source'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0375
_diffrn_reflns_av_unetI/netI     0.0265
_diffrn_reflns_limit_h_max       7
_diffrn_reflns_limit_h_min       -7
_diffrn_reflns_limit_k_max       18
_diffrn_reflns_limit_k_min       -18
_diffrn_reflns_limit_l_max       21
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            17057
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         27.572
_diffrn_reflns_theta_min         2.472
_diffrn_source                   microsource
_exptl_absorpt_coefficient_mu    0.282
_exptl_absorpt_correction_T_max  0.971
_exptl_absorpt_correction_T_min  0.788
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
(SADABS; Krause et al., 2015)
;
_exptl_crystal_colour            'pale yellow'
_exptl_crystal_density_diffrn    1.440
_exptl_crystal_description       'cut block'
_exptl_crystal_F_000             624
_exptl_crystal_size_max          0.260
_exptl_crystal_size_mid          0.230
_exptl_crystal_size_min          0.220
_refine_diff_density_max         0.214
_refine_diff_density_min         -0.158
_refine_ls_abs_structure_details
;
Flack x determined using 1035 quotients [(I+)-(I-)]/[(I+)+(I-)]
[Parsons et al. (2013)
;
_refine_ls_abs_structure_Flack   0.01(2)
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.065
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     190
_refine_ls_number_reflns         2896
_refine_ls_number_restraints     1
_refine_ls_restrained_S_all      1.065
_refine_ls_R_factor_all          0.0371
_refine_ls_R_factor_gt           0.0334
_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)+(0.0322P)²+0.4666P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0806
_refine_ls_wR_factor_ref         0.0827
_reflns_number_gt                2694
_reflns_number_total             2896
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            vm2285sup1.cif
_cod_data_source_block           I
_cod_database_code               2022806
_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   0.930
_shelx_estimated_absorpt_t_max   0.940
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, -y, z+1/2'
'x+1/2, -y+1/2, z'
'-x+1/2, 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
_atom_site_disorder_assembly
_atom_site_disorder_group
Cl Cl1 0.86056(16) 0.65710(6) 0.91506(5) 0.0577(3) Uani d 1 . .
O O1 -0.0096(3) 0.59370(18) 0.48876(12) 0.0505(6) Uani d 1 . .
O O2 0.0030(3) 0.57318(14) 0.18914(12) 0.0416(5) Uani d 1 . .
O O3 0.4399(4) 0.64129(16) 0.14256(12) 0.0443(5) Uani d 1 . .
C C1 0.1903(5) 0.6112(2) 0.47247(15) 0.0338(6) Uani d 1 . .
C C2 0.2634(4) 0.61897(18) 0.38646(15) 0.0286(5) Uani d 1 . .
C C3 0.1080(4) 0.59307(18) 0.32641(17) 0.0318(5) Uani d 1 . .
H H3 -0.038161 0.570520 0.341626 0.038 Uiso calc 1 . .
C C4 0.1637(4) 0.59976(17) 0.24503(16) 0.0300(5) Uani d 1 . .
C C5 0.0414(6) 0.6143(2) 0.11107(17) 0.0453(7) Uani d 1 . .
H H5A 0.008461 0.681919 0.113519 0.054 Uiso calc 1 . .
H H5B -0.062554 0.585853 0.070731 0.054 Uiso calc 1 . .
C C6 0.2829(6) 0.5995(2) 0.08557(18) 0.0475(8) Uani d 1 . .
H H6A 0.313824 0.531780 0.081738 0.057 Uiso calc 1 . .
H H6B 0.306758 0.627076 0.031178 0.057 Uiso calc 1 . .
C C7 0.3778(5) 0.63300(19) 0.22209(16) 0.0320(6) Uani d 1 . .
C C8 0.5313(5) 0.66010(18) 0.28102(18) 0.0343(6) Uani d 1 . .
H H8 0.675979 0.683954 0.265581 0.041 Uiso calc 1 . .
C C9 0.4761(5) 0.65280(18) 0.36243(17) 0.0329(6) Uani d 1 . .
H H9 0.584046 0.671004 0.402365 0.040 Uiso calc 1 . .
C C10 0.3628(5) 0.62304(19) 0.53720(16) 0.0361(6) Uani d 1 . .
H H10 0.511960 0.643759 0.523877 0.043 Uiso calc 1 . .
C C11 0.3090(5) 0.60465(18) 0.61436(15) 0.0314(6) Uani d 1 . .
H H11 0.158246 0.583195 0.624038 0.038 Uiso calc 1 . .
C C12 0.4563(4) 0.61380(17) 0.68570(15) 0.0297(5) Uani d 1 . .
C C13 0.6738(4) 0.65334(18) 0.68259(17) 0.0326(5) Uani d 1 . .
H H13 0.737075 0.671519 0.631943 0.039 Uiso calc 1 . .
C C14 0.7979(5) 0.66609(18) 0.75398(18) 0.0347(6) Uani d 1 . .
H H14 0.945533 0.693264 0.752293 0.042 Uiso calc 1 . .
C C15 0.7047(5) 0.63898(18) 0.82670(18) 0.0355(6) Uani d 1 . .
C C16 0.4927(5) 0.59816(19) 0.83158(18) 0.0367(6) Uani d 1 . .
H H16 0.432553 0.578743 0.882366 0.044 Uiso calc 1 . .
C C17 0.3696(5) 0.58612(18) 0.76102(16) 0.0330(6) Uani d 1 . .
H H17 0.222733 0.558409 0.763644 0.040 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'
Cl Cl 0.1484 0.1585 '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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C4 O2 C5 . . 112.4(2) ?
C7 O3 C6 . . 114.7(2) ?
O1 C1 C10 . . 121.2(2) ?
O1 C1 C2 . . 120.0(2) ?
C10 C1 C2 . . 118.8(2) ?
C3 C2 C9 . . 118.4(2) ?
C3 C2 C1 . . 117.9(2) ?
C9 C2 C1 . . 123.7(2) ?
C4 C3 C2 . . 121.0(2) ?
C4 C3 H3 . . 119.5 ?
C2 C3 H3 . . 119.5 ?
O2 C4 C3 . . 118.0(2) ?
O2 C4 C7 . . 122.1(3) ?
C3 C4 C7 . . 119.9(2) ?
O2 C5 C6 . . 110.0(3) ?
O2 C5 H5A . . 109.7 ?
C6 C5 H5A . . 109.7 ?
O2 C5 H5B . . 109.7 ?
C6 C5 H5B . . 109.7 ?
H5A C5 H5B . . 108.2 ?
O3 C6 C5 . . 111.2(2) ?
O3 C6 H6A . . 109.4 ?
C5 C6 H6A . . 109.4 ?
O3 C6 H6B . . 109.4 ?
C5 C6 H6B . . 109.4 ?
H6A C6 H6B . . 108.0 ?
O3 C7 C8 . . 118.5(3) ?
O3 C7 C4 . . 122.0(3) ?
C8 C7 C4 . . 119.5(3) ?
C7 C8 C9 . . 120.5(2) ?
C7 C8 H8 . . 119.7 ?
C9 C8 H8 . . 119.7 ?
C8 C9 C2 . . 120.7(2) ?
C8 C9 H9 . . 119.7 ?
C2 C9 H9 . . 119.7 ?
C11 C10 C1 . . 120.1(3) ?
C11 C10 H10 . . 119.9 ?
C1 C10 H10 . . 119.9 ?
C10 C11 C12 . . 127.4(3) ?
C10 C11 H11 . . 116.3 ?
C12 C11 H11 . . 116.3 ?
C13 C12 C17 . . 118.7(2) ?
C13 C12 C11 . . 123.0(2) ?
C17 C12 C11 . . 118.2(2) ?
C14 C13 C12 . . 119.9(3) ?
C14 C13 H13 . . 120.0 ?
C12 C13 H13 . . 120.0 ?
C15 C14 C13 . . 119.4(3) ?
C15 C14 H14 . . 120.3 ?
C13 C14 H14 . . 120.3 ?
C14 C15 C16 . . 122.1(3) ?
C14 C15 Cl1 . . 118.6(2) ?
C16 C15 Cl1 . . 119.3(2) ?
C15 C16 C17 . . 118.5(3) ?
C15 C16 H16 . . 120.8 ?
C17 C16 H16 . . 120.8 ?
C16 C17 C12 . . 121.5(3) ?
C16 C17 H17 . . 119.3 ?
C12 C17 H17 . . 119.3 ?
loop_
_geom_bond_atom_site_label_1
_geom_bond_atom_site_label_2
_geom_bond_site_symmetry_2
_geom_bond_distance
_geom_bond_publ_flag
Cl1 C15 . 1.739(3) ?
O1 C1 . 1.229(3) ?
O2 C4 . 1.372(3) ?
O2 C5 . 1.433(3) ?
O3 C7 . 1.366(3) ?
O3 C6 . 1.446(4) ?
C1 C10 . 1.480(4) ?
C1 C2 . 1.485(3) ?
C2 C3 . 1.396(4) ?
C2 C9 . 1.396(4) ?
C3 C4 . 1.384(4) ?
C3 H3 . 0.9500 ?
C4 C7 . 1.395(4) ?
C5 C6 . 1.493(5) ?
C5 H5A . 0.9900 ?
C5 H5B . 0.9900 ?
C6 H6A . 0.9900 ?
C6 H6B . 0.9900 ?
C7 C8 . 1.380(4) ?
C8 C9 . 1.384(4) ?
C8 H8 . 0.9500 ?
C9 H9 . 0.9500 ?
C10 C11 . 1.336(4) ?
C10 H10 . 0.9500 ?
C11 C12 . 1.465(4) ?
C11 H11 . 0.9500 ?
C12 C13 . 1.397(4) ?
C12 C17 . 1.399(4) ?
C13 C14 . 1.396(4) ?
C13 H13 . 0.9500 ?
C14 C15 . 1.373(4) ?
C14 H14 . 0.9500 ?
C15 C16 . 1.377(4) ?
C16 C17 . 1.379(4) ?
C16 H16 . 0.9500 ?
C17 H17 . 0.9500 ?
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
_geom_hbond_publ_flag
C5 H5A O3 3_465 0.99 2.61 3.595(4) 172 yes
C5 H5B Cl1 1_454 0.99 2.80 3.455(3) 124 yes
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_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion
_geom_torsion_publ_flag
O1 C1 C2 C3 . . . . -8.9(4) ?
C10 C1 C2 C3 . . . . 169.9(2) ?
O1 C1 C2 C9 . . . . 169.5(3) ?
C10 C1 C2 C9 . . . . -11.7(4) ?
C9 C2 C3 C4 . . . . 0.7(4) ?
C1 C2 C3 C4 . . . . 179.1(2) ?
C5 O2 C4 C3 . . . . 158.0(3) ?
C5 O2 C4 C7 . . . . -21.8(4) ?
C2 C3 C4 O2 . . . . -180.0(2) ?
C2 C3 C4 C7 . . . . -0.1(4) ?
C4 O2 C5 C6 . . . . 50.4(3) ?
C7 O3 C6 C5 . . . . 38.6(4) ?
O2 C5 C6 O3 . . . . -60.1(4) ?
C6 O3 C7 C8 . . . . 171.8(3) ?
C6 O3 C7 C4 . . . . -9.4(4) ?
O2 C4 C7 O3 . . . . 0.2(4) ?
C3 C4 C7 O3 . . . . -179.6(3) ?
O2 C4 C7 C8 . . . . 179.0(2) ?
C3 C4 C7 C8 . . . . -0.8(4) ?
O3 C7 C8 C9 . . . . -179.9(3) ?
C4 C7 C8 C9 . . . . 1.3(4) ?
C7 C8 C9 C2 . . . . -0.8(4) ?
C3 C2 C9 C8 . . . . -0.2(4) ?
C1 C2 C9 C8 . . . . -178.6(3) ?
O1 C1 C10 C11 . . . . 7.4(4) ?
C2 C1 C10 C11 . . . . -171.3(3) ?
C1 C10 C11 C12 . . . . -179.0(2) ?
C10 C11 C12 C13 . . . . 6.8(4) ?
C10 C11 C12 C17 . . . . -176.7(3) ?
C17 C12 C13 C14 . . . . -1.2(4) ?
C11 C12 C13 C14 . . . . 175.3(2) ?
C12 C13 C14 C15 . . . . 0.4(4) ?
C13 C14 C15 C16 . . . . 0.9(4) ?
C13 C14 C15 Cl1 . . . . -179.0(2) ?
C14 C15 C16 C17 . . . . -1.3(4) ?
Cl1 C15 C16 C17 . . . . 178.7(2) ?
C15 C16 C17 C12 . . . . 0.4(4) ?
C13 C12 C17 C16 . . . . 0.8(4) ?
C11 C12 C17 C16 . . . . -175.8(2) ?

_cod_database_fobs_code 2022806
