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#$Date: 2022-06-17 01:52:41 +0300 (Fri, 17 Jun 2022) $
#$Revision: 276071 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/71/05/7710502.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_7710502
loop_
_publ_author_name
'Malankar, Gauri S.'
'Shelar, Divyesh S.'
'Butcher, R. J.'
'Manjare, Sudesh T.'
_publ_section_title
;
 Synthesis and Single Crystal X-ray Study of Phenylselenyl Embedded
 Coumarin-Based Sensors for Selective Detection of Superoxide
;
_journal_name_full               'Dalton Transactions'
_journal_paper_doi               10.1039/D2DT01079H
_journal_year                    2022
_chemical_formula_moiety         'C16 H12 O3 Se, H2 O'
_chemical_formula_sum            'C16 H14 O4 Se'
_chemical_formula_weight         349.23
_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'
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2022-03-05 deposited with the CCDC.	2022-06-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.690(4)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.3926(7)
_cell_length_b                   11.6371(7)
_cell_length_c                   11.9617(6)
_cell_measurement_reflns_used    6038
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      28.85
_cell_measurement_theta_min      2.44
_cell_volume                     1446.02(15)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL (Sheldrick, 2008)'
_computing_publication_material  'Bruker SHELXTL (Sheldrick, 2008)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.993
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0534
_diffrn_reflns_av_unetI/netI     0.0844
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.993
_diffrn_reflns_number            17974
_diffrn_reflns_point_group_measured_fraction_full 0.998
_diffrn_reflns_point_group_measured_fraction_max 0.993
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.655
_diffrn_reflns_theta_min         2.628
_exptl_absorpt_coefficient_mu    2.609
_exptl_absorpt_correction_T_max  0.7459
_exptl_absorpt_correction_T_min  0.4348
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sadabs (Sheldrick, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.604
_exptl_crystal_description       prism
_exptl_crystal_F_000             704
_exptl_crystal_size_max          0.24
_exptl_crystal_size_mid          0.17
_exptl_crystal_size_min          0.09
_refine_diff_density_max         1.114
_refine_diff_density_min         -0.707
_refine_diff_density_rms         0.126
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     200
_refine_ls_number_reflns         4066
_refine_ls_number_restraints     3
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0879
_refine_ls_R_factor_gt           0.0514
_refine_ls_shift/su_max          0.001
_refine_ls_shift/su_mean         0.000
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0554P)²+0.6812P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1099
_refine_ls_wR_factor_ref         0.1233
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2849
_reflns_number_total             4066
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2dt01079h2.cif
_cod_data_source_block           Probe_4
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7710502
_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.
;
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_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
Se1 Se 0.68220(3) 0.45496(3) 0.07573(3) 0.02314(12) Uani 1 1 d . . . . .
O1 O 0.8546(2) 0.67335(16) 0.42974(16) 0.0186(5) Uani 1 1 d . . . . .
O2 O 0.8814(2) 0.84200(18) 0.35126(19) 0.0264(5) Uani 1 1 d . . . . .
O3 O 0.8259(3) 0.31828(18) 0.62210(18) 0.0259(5) Uani 1 1 d . . . . .
H3O H 0.808825 0.362391 0.675235 0.082(19) Uiso 1 1 calc R . . . .
O1W O 0.7797(4) 0.4491(2) 0.7962(2) 0.0463(8) Uani 1 1 d D . . . .
H1W1 H 0.811(5) 0.511(2) 0.810(4) 0.061(16) Uiso 1 1 d D . . . .
H1W2 H 0.736(5) 0.433(4) 0.849(3) 0.066(17) Uiso 1 1 d D . . . .
C1 C 0.8712(3) 0.7389(3) 0.3356(2) 0.0202(6) Uani 1 1 d . . . . .
C2 C 0.8725(3) 0.6808(2) 0.2300(2) 0.0201(6) Uani 1 1 d . . . . .
H2A H 0.877928 0.725054 0.163571 0.024 Uiso 1 1 calc R U . . .
C3 C 0.8662(3) 0.5644(2) 0.2218(3) 0.0180(6) Uani 1 1 d . . . . .
C4 C 0.8595(3) 0.4970(3) 0.3227(2) 0.0167(6) Uani 1 1 d . . . . .
C5 C 0.8617(3) 0.3762(2) 0.3279(2) 0.0194(6) Uani 1 1 d . . . . .
H5A H 0.869774 0.333395 0.260850 0.023 Uiso 1 1 calc R U . . .
C6 C 0.8525(3) 0.3188(2) 0.4273(2) 0.0210(7) Uani 1 1 d . . . . .
H6A H 0.856662 0.237293 0.428910 0.025 Uiso 1 1 calc R U . . .
C7 C 0.8368(3) 0.3806(2) 0.5269(2) 0.0188(6) Uani 1 1 d . . . . .
C8 C 0.8354(3) 0.5002(3) 0.5260(2) 0.0191(6) Uani 1 1 d . . . . .
H8A H 0.824872 0.542665 0.592930 0.023 Uiso 1 1 calc R U . . .
C9 C 0.8496(3) 0.5553(2) 0.4249(2) 0.0174(6) Uani 1 1 d . . . . .
C10 C 0.8604(3) 0.5083(3) 0.1097(2) 0.0205(6) Uani 1 1 d . . . . .
H10A H 0.920285 0.442096 0.109222 0.025 Uiso 1 1 calc R U . . .
H10B H 0.887051 0.563576 0.051931 0.025 Uiso 1 1 calc R U . . .
C11 C 0.5994(3) 0.6026(3) 0.0898(3) 0.0249(7) Uani 1 1 d . . . . .
C12 C 0.5363(4) 0.6283(3) 0.1871(3) 0.0350(8) Uani 1 1 d . . . . .
H12A H 0.533309 0.573383 0.245717 0.042 Uiso 1 1 calc R U . . .
C13 C 0.4775(4) 0.7342(4) 0.1985(3) 0.0402(9) Uani 1 1 d . . . . .
H13A H 0.433781 0.751614 0.265057 0.048 Uiso 1 1 calc R U . . .
C14 C 0.4818(4) 0.8147(3) 0.1142(4) 0.0404(9) Uani 1 1 d . . . . .
H14A H 0.441760 0.887437 0.123020 0.048 Uiso 1 1 calc R U . . .
C15 C 0.5445(4) 0.7896(3) 0.0165(4) 0.0409(9) Uani 1 1 d . . . . .
H15A H 0.547621 0.844702 -0.041939 0.049 Uiso 1 1 calc R U . . .
C16 C 0.6029(4) 0.6826(3) 0.0047(3) 0.0308(8) Uani 1 1 d . . . . .
H16A H 0.645346 0.664621 -0.062321 0.037 Uiso 1 1 calc R U . . .
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'
Se Se -0.0929 2.2259 '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
C11 Se1 C10 96.88(13) . . ?
C1 O1 C9 121.6(2) . . ?
C7 O3 H3O 109.5 . . ?
H1W1 O1W H1W2 107(3) . . ?
O2 C1 O1 115.6(3) . . ?
O2 C1 C2 126.7(3) . . ?
O1 C1 C2 117.7(2) . . ?
C3 C2 C1 122.2(3) . . ?
C3 C2 H2A 118.9 . . ?
C1 C2 H2A 118.9 . . ?
C2 C3 C4 119.0(3) . . ?
C2 C3 C10 120.2(3) . . ?
C4 C3 C10 120.8(3) . . ?
C9 C4 C5 116.5(3) . . ?
C9 C4 C3 118.2(3) . . ?
C5 C4 C3 125.4(3) . . ?
C6 C5 C4 121.6(3) . . ?
C6 C5 H5A 119.2 . . ?
C4 C5 H5A 119.2 . . ?
C5 C6 C7 120.0(3) . . ?
C5 C6 H6A 120.0 . . ?
C7 C6 H6A 120.0 . . ?
O3 C7 C8 122.6(3) . . ?
O3 C7 C6 116.9(2) . . ?
C8 C7 C6 120.4(3) . . ?
C9 C8 C7 118.0(3) . . ?
C9 C8 H8A 121.0 . . ?
C7 C8 H8A 121.0 . . ?
O1 C9 C8 115.6(3) . . ?
O1 C9 C4 121.0(3) . . ?
C8 C9 C4 123.4(3) . . ?
C3 C10 Se1 109.5(2) . . ?
C3 C10 H10A 109.8 . . ?
Se1 C10 H10A 109.8 . . ?
C3 C10 H10B 109.8 . . ?
Se1 C10 H10B 109.8 . . ?
H10A C10 H10B 108.2 . . ?
C16 C11 C12 119.8(3) . . ?
C16 C11 Se1 121.0(3) . . ?
C12 C11 Se1 119.2(3) . . ?
C13 C12 C11 119.7(4) . . ?
C13 C12 H12A 120.1 . . ?
C11 C12 H12A 120.1 . . ?
C14 C13 C12 120.6(4) . . ?
C14 C13 H13A 119.7 . . ?
C12 C13 H13A 119.7 . . ?
C13 C14 C15 120.0(4) . . ?
C13 C14 H14A 120.0 . . ?
C15 C14 H14A 120.0 . . ?
C14 C15 C16 119.4(4) . . ?
C14 C15 H15A 120.3 . . ?
C16 C15 H15A 120.3 . . ?
C11 C16 C15 120.5(4) . . ?
C11 C16 H16A 119.8 . . ?
C15 C16 H16A 119.8 . . ?
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
Se1 C11 1.931(3) . ?
Se1 C10 1.984(3) . ?
O1 C1 1.375(3) . ?
O1 C9 1.375(3) . ?
O2 C1 1.219(4) . ?
O3 C7 1.358(3) . ?
O3 H3O 0.8400 . ?
O1W H1W1 0.808(18) . ?
O1W H1W2 0.811(19) . ?
C1 C2 1.433(4) . ?
C2 C3 1.359(4) . ?
C2 H2A 0.9500 . ?
C3 C4 1.443(4) . ?
C3 C10 1.491(4) . ?
C4 C9 1.404(4) . ?
C4 C5 1.408(4) . ?
C5 C6 1.369(4) . ?
C5 H5A 0.9500 . ?
C6 C7 1.404(4) . ?
C6 H6A 0.9500 . ?
C7 C8 1.392(4) . ?
C8 C9 1.381(4) . ?
C8 H8A 0.9500 . ?
C10 H10A 0.9900 . ?
C10 H10B 0.9900 . ?
C11 C16 1.380(5) . ?
C11 C12 1.385(5) . ?
C12 C13 1.385(5) . ?
C12 H12A 0.9500 . ?
C13 C14 1.378(6) . ?
C13 H13A 0.9500 . ?
C14 C15 1.386(6) . ?
C14 H14A 0.9500 . ?
C15 C16 1.394(5) . ?
C15 H15A 0.9500 . ?
C16 H16A 0.9500 . ?
loop_
_geom_hbond_atom_site_label_D
_geom_hbond_atom_site_label_H
_geom_hbond_atom_site_label_A
_geom_hbond_distance_DH
_geom_hbond_distance_HA
_geom_hbond_distance_DA
_geom_hbond_angle_DHA
_geom_hbond_site_symmetry_A
_geom_hbond_publ_flag
O3 H3O O1W 0.84 1.80 2.635(3) 175.4 . yes
O1W H1W1 O2 0.808(18) 1.92(2) 2.724(3) 176(5) 4_576 yes
O1W H1W2 Se1 0.811(19) 2.80(3) 3.523(3) 150(4) 1_556 yes
C10 H10A O2 0.99 2.40 3.329(4) 155.7 2_745 yes
C10 H10B O2 0.99 2.64 3.561(4) 155.1 4_575 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
_geom_torsion_site_symmetry_1
_geom_torsion_site_symmetry_2
_geom_torsion_site_symmetry_3
_geom_torsion_site_symmetry_4
_geom_torsion_publ_flag
C9 O1 C1 O2 -176.0(3) . . . . ?
C9 O1 C1 C2 5.1(4) . . . . ?
O2 C1 C2 C3 177.0(3) . . . . ?
O1 C1 C2 C3 -4.3(5) . . . . ?
C1 C2 C3 C4 -0.7(5) . . . . ?
C1 C2 C3 C10 176.6(3) . . . . ?
C2 C3 C4 C9 4.9(4) . . . . ?
C10 C3 C4 C9 -172.4(3) . . . . ?
C2 C3 C4 C5 -175.3(3) . . . . ?
C10 C3 C4 C5 7.4(5) . . . . ?
C9 C4 C5 C6 1.1(5) . . . . ?
C3 C4 C5 C6 -178.8(3) . . . . ?
C4 C5 C6 C7 1.8(5) . . . . ?
C5 C6 C7 O3 178.8(3) . . . . ?
C5 C6 C7 C8 -2.4(5) . . . . ?
O3 C7 C8 C9 178.8(3) . . . . ?
C6 C7 C8 C9 0.0(5) . . . . ?
C1 O1 C9 C8 178.6(3) . . . . ?
C1 O1 C9 C4 -1.0(4) . . . . ?
C7 C8 C9 O1 -176.6(3) . . . . ?
C7 C8 C9 C4 3.0(5) . . . . ?
C5 C4 C9 O1 176.0(3) . . . . ?
C3 C4 C9 O1 -4.2(4) . . . . ?
C5 C4 C9 C8 -3.6(5) . . . . ?
C3 C4 C9 C8 176.3(3) . . . . ?
C2 C3 C10 Se1 -104.3(3) . . . . ?
C4 C3 C10 Se1 73.0(3) . . . . ?
C16 C11 C12 C13 -0.2(6) . . . . ?
Se1 C11 C12 C13 179.4(3) . . . . ?
C11 C12 C13 C14 -0.4(6) . . . . ?
C12 C13 C14 C15 0.5(6) . . . . ?
C13 C14 C15 C16 -0.1(6) . . . . ?
C12 C11 C16 C15 0.7(5) . . . . ?
Se1 C11 C16 C15 -179.0(3) . . . . ?
C14 C15 C16 C11 -0.5(6) . . . . ?
