#------------------------------------------------------------------------------
#$Date: 2022-06-17 01:52:41 +0300 (Fri, 17 Jun 2022) $
#$Revision: 276071 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/71/05/7710503.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_7710503
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         'C18 H14 O4.08 Se'
_chemical_formula_sum            'C18 H14 O4.08 Se'
_chemical_formula_weight         374.54
_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
_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                106.478(3)
_cell_angle_beta                 104.683(2)
_cell_angle_gamma                103.015(2)
_cell_formula_units_Z            2
_cell_length_a                   7.6073(5)
_cell_length_b                   9.4274(9)
_cell_length_c                   12.1570(11)
_cell_measurement_reflns_used    9961
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      32.49
_cell_measurement_theta_min      2.44
_cell_volume                     766.15(11)
_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, 2015b)'
_computing_structure_solution    'SHELXT (Sheldrick, 2015a)'
_diffrn_ambient_temperature      100(2)
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.997
_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  0.0345
_diffrn_reflns_av_unetI/netI     0.0421
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.997
_diffrn_reflns_number            5560
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.997
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         32.563
_diffrn_reflns_theta_min         2.378
_exptl_absorpt_coefficient_mu    2.469
_exptl_absorpt_correction_T_max  0.7464
_exptl_absorpt_correction_T_min  0.6314
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'Sadabs (Sheldrick, 1996)'
_exptl_crystal_colour            colorless
_exptl_crystal_density_diffrn    1.624
_exptl_crystal_description       prism
_exptl_crystal_F_000             377
_exptl_crystal_size_max          0.21
_exptl_crystal_size_mid          0.16
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.540
_refine_diff_density_min         -0.415
_refine_diff_density_rms         0.074
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.027
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     220
_refine_ls_number_reflns         5560
_refine_ls_number_restraints     7
_refine_ls_restrained_S_all      1.027
_refine_ls_R_factor_all          0.0382
_refine_ls_R_factor_gt           0.0295
_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)+(0.0224P)²+0.3178P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0639
_refine_ls_wR_factor_ref         0.0669
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4814
_reflns_number_total             5560
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2dt01079h2.cif
_cod_data_source_block           Probe_5
_cod_database_code               7710503
_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, -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
Se Se 0.27739(2) 0.06836(2) 0.62935(2) 0.01977(5) Uani 1 1 d . . . . .
O1 O 0.58863(17) 0.28051(15) 0.29590(10) 0.0280(2) Uani 1 1 d . . . . .
O2 O 0.76387(14) 0.39925(12) 0.49129(9) 0.0197(2) Uani 1 1 d . . . . .
O3 O 1.29187(16) 0.48803(13) 0.87663(10) 0.0236(2) Uani 1 1 d . . . . .
C1 C 0.43891(19) 0.31029(16) 0.55669(13) 0.0165(2) Uani 1 1 d . . . . .
C2 C 0.4252(2) 0.26958(17) 0.43779(13) 0.0192(3) Uani 1 1 d . . . . .
H2A H 0.303427 0.210496 0.376902 0.023 Uiso 1 1 calc R U . . .
C3 C 0.5895(2) 0.31278(17) 0.39990(13) 0.0203(3) Uani 1 1 d . . . . .
O4 O 1.16696(14) 0.68533(12) 0.90185(9) 0.0205(2) Uani 1 1 d . . . . .
C4 C 0.7815(2) 0.44482(16) 0.61296(12) 0.0162(2) Uani 1 1 d . . . . .
C5 C 0.9639(2) 0.53509(16) 0.69465(13) 0.0181(3) Uani 1 1 d . . . . .
H5A H 1.068499 0.562280 0.667101 0.022 Uiso 1 1 calc R U . . .
C6 C 0.98798(19) 0.58396(16) 0.81744(13) 0.0177(2) Uani 1 1 d . . . . .
C7 C 0.8373(2) 0.54747(16) 0.86036(13) 0.0187(3) Uani 1 1 d . U . . .
H7A H 0.858086 0.583169 0.945385 0.022 Uiso 0.919(4) 1 calc R U P A 1
C8 C 0.6562(2) 0.45813(16) 0.77697(13) 0.0177(2) Uani 1 1 d . . . . .
H8A H 0.552153 0.433115 0.805379 0.021 Uiso 1 1 calc R U . . .
C9 C 0.62398(19) 0.40380(15) 0.65072(12) 0.0157(2) Uani 1 1 d . . . . .
C10 C 1.3150(2) 0.62501(17) 0.91991(12) 0.0180(3) Uani 1 1 d . . . . .
C11 C 1.5001(2) 0.75170(19) 0.99854(14) 0.0242(3) Uani 1 1 d . . . . .
H11A H 1.593594 0.706109 1.033606 0.036 Uiso 1 1 calc R U . . .
H11B H 1.478656 0.826354 1.064359 0.036 Uiso 1 1 calc R U . . .
H11C H 1.549341 0.805683 0.949202 0.036 Uiso 1 1 calc R U . . .
C12 C 0.2645(2) 0.25596(16) 0.58938(13) 0.0183(3) Uani 1 1 d . . . . .
H12A H 0.146422 0.230171 0.519908 0.022 Uiso 1 1 calc R U . . .
H12B H 0.263323 0.338844 0.660369 0.022 Uiso 1 1 calc R U . . .
C13 C 0.09781(19) 0.05895(16) 0.71465(12) 0.0170(2) Uani 1 1 d . . . . .
C14 C 0.1017(2) -0.03798(16) 0.78337(13) 0.0187(3) Uani 1 1 d . . . . .
H14A H 0.189322 -0.095641 0.785523 0.022 Uiso 1 1 calc R U . . .
C15 C -0.0240(2) -0.04873(17) 0.84834(13) 0.0215(3) Uani 1 1 d . . . . .
H15A H -0.022342 -0.114596 0.894737 0.026 Uiso 1 1 calc R U . . .
C16 C -0.1521(2) 0.03561(17) 0.84625(14) 0.0235(3) Uani 1 1 d . . . . .
H16A H -0.236223 0.028629 0.891862 0.028 Uiso 1 1 calc R U . . .
C17 C -0.1564(2) 0.13003(17) 0.77717(15) 0.0234(3) Uani 1 1 d . . . . .
H17A H -0.244412 0.187342 0.775210 0.028 Uiso 1 1 calc R U . . .
C18 C -0.0327(2) 0.14159(17) 0.71056(14) 0.0208(3) Uani 1 1 d . . . . .
H18A H -0.037433 0.205501 0.662613 0.025 Uiso 1 1 calc R U . . .
O1A O 0.8971(15) 0.6110(12) 0.9882(9) 0.009(3) Uani 0.081(4) 1 d . U P A 2
H1A H 0.894292 0.538877 1.016038 0.014 Uiso 0.081(4) 1 calc R U P A 2
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
C13 Se C12 100.03(6) . . ?
C4 O2 C3 121.84(11) . . ?
C2 C1 C9 119.20(12) . . ?
C2 C1 C12 119.68(13) . . ?
C9 C1 C12 121.10(12) . . ?
C1 C2 C3 122.55(13) . . ?
C1 C2 H2A 118.7 . . ?
C3 C2 H2A 118.7 . . ?
O1 C3 O2 116.76(13) . . ?
O1 C3 C2 126.34(14) . . ?
O2 C3 C2 116.90(12) . . ?
C10 O4 C6 117.42(11) . . ?
O2 C4 C5 115.64(12) . . ?
O2 C4 C9 121.80(12) . . ?
C5 C4 C9 122.55(13) . . ?
C6 C5 C4 117.60(12) . . ?
C6 C5 H5A 121.2 . . ?
C4 C5 H5A 121.2 . . ?
C5 C6 C7 122.48(13) . . ?
C5 C6 O4 118.97(12) . . ?
C7 C6 O4 118.31(13) . . ?
C8 C7 C6 118.84(13) . . ?
C8 C7 O1A 129.3(5) . . ?
C6 C7 O1A 111.9(5) . . ?
C8 C7 H7A 120.6 . . ?
C6 C7 H7A 120.6 . . ?
C7 C8 C9 121.06(13) . . ?
C7 C8 H8A 119.5 . . ?
C9 C8 H8A 119.5 . . ?
C4 C9 C8 117.47(12) . . ?
C4 C9 C1 117.68(12) . . ?
C8 C9 C1 124.84(12) . . ?
O3 C10 O4 122.45(13) . . ?
O3 C10 C11 126.88(14) . . ?
O4 C10 C11 110.67(12) . . ?
C10 C11 H11A 109.5 . . ?
C10 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
C10 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
C1 C12 Se 107.13(9) . . ?
C1 C12 H12A 110.3 . . ?
Se C12 H12A 110.3 . . ?
C1 C12 H12B 110.3 . . ?
Se C12 H12B 110.3 . . ?
H12A C12 H12B 108.5 . . ?
C18 C13 C14 120.09(13) . . ?
C18 C13 Se 123.43(11) . . ?
C14 C13 Se 116.48(11) . . ?
C15 C14 C13 119.25(13) . . ?
C15 C14 H14A 120.4 . . ?
C13 C14 H14A 120.4 . . ?
C16 C15 C14 120.85(14) . . ?
C16 C15 H15A 119.6 . . ?
C14 C15 H15A 119.6 . . ?
C17 C16 C15 119.56(14) . . ?
C17 C16 H16A 120.2 . . ?
C15 C16 H16A 120.2 . . ?
C16 C17 C18 120.56(14) . . ?
C16 C17 H17A 119.7 . . ?
C18 C17 H17A 119.7 . . ?
C13 C18 C17 119.68(13) . . ?
C13 C18 H18A 120.2 . . ?
C17 C18 H18A 120.2 . . ?
C7 O1A H1A 109.5 . . ?
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
Se C13 1.9145(14) . ?
Se C12 1.9787(14) . ?
O1 C3 1.2115(18) . ?
O2 C4 1.3796(16) . ?
O2 C3 1.3822(17) . ?
O3 C10 1.2004(18) . ?
C1 C2 1.3559(19) . ?
C1 C9 1.4558(19) . ?
C1 C12 1.5022(19) . ?
C2 C3 1.452(2) . ?
C2 H2A 0.9500 . ?
O4 C10 1.3686(17) . ?
O4 C6 1.4034(17) . ?
C4 C5 1.3880(19) . ?
C4 C9 1.4025(18) . ?
C5 C6 1.381(2) . ?
C5 H5A 0.9500 . ?
C6 C7 1.3900(19) . ?
C7 C8 1.385(2) . ?
C7 O1A 1.404(10) . ?
C7 H7A 0.9500 . ?
C8 C9 1.4088(19) . ?
C8 H8A 0.9500 . ?
C10 C11 1.495(2) . ?
C11 H11A 0.9800 . ?
C11 H11B 0.9800 . ?
C11 H11C 0.9800 . ?
C12 H12A 0.9900 . ?
C12 H12B 0.9900 . ?
C13 C18 1.393(2) . ?
C13 C14 1.4024(19) . ?
C14 C15 1.391(2) . ?
C14 H14A 0.9500 . ?
C15 C16 1.389(2) . ?
C15 H15A 0.9500 . ?
C16 C17 1.386(2) . ?
C16 H16A 0.9500 . ?
C17 C18 1.394(2) . ?
C17 H17A 0.9500 . ?
C18 H18A 0.9500 . ?
O1A H1A 0.8400 . ?
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
C5 H5A O1 0.95 2.55 3.4123(18) 151.5 2_766 yes
C5 H5A O2 0.95 2.63 3.5171(17) 156.3 2_766 yes
C8 H8A O3 0.95 2.45 3.3302(18) 153.6 1_455 yes
C11 H11A O3 0.98 2.58 3.501(2) 156.0 2_867 yes
C12 H12B O3 0.99 2.53 3.4810(18) 160.4 1_455 yes
O1A^b H1A^b O3 0.84 2.18 2.665(11) 117.0 2_767 yes
O1A^b H1A^b O4 0.84 2.58 3.416(11) 171.4 2_767 yes
O1A^b H1A^b O1A^b 0.84 2.35 2.92(2) 125.1 2_767 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 C1 C2 C3 1.4(2) . . . . ?
C12 C1 C2 C3 -177.49(13) . . . . ?
C4 O2 C3 O1 178.98(13) . . . . ?
C4 O2 C3 C2 -1.0(2) . . . . ?
C1 C2 C3 O1 179.80(15) . . . . ?
C1 C2 C3 O2 -0.3(2) . . . . ?
C3 O2 C4 C5 -178.15(12) . . . . ?
C3 O2 C4 C9 1.0(2) . . . . ?
O2 C4 C5 C6 179.70(12) . . . . ?
C9 C4 C5 C6 0.5(2) . . . . ?
C4 C5 C6 C7 -0.7(2) . . . . ?
C4 C5 C6 O4 -175.09(12) . . . . ?
C10 O4 C6 C5 -71.44(17) . . . . ?
C10 O4 C6 C7 113.98(14) . . . . ?
C5 C6 C7 C8 0.3(2) . . . . ?
O4 C6 C7 C8 174.68(12) . . . . ?
C5 C6 C7 O1A -179.6(5) . . . . ?
O4 C6 C7 O1A -5.2(5) . . . . ?
C6 C7 C8 C9 0.4(2) . . . . ?
O1A C7 C8 C9 -179.7(6) . . . . ?
O2 C4 C9 C8 -179.01(12) . . . . ?
C5 C4 C9 C8 0.1(2) . . . . ?
O2 C4 C9 C1 0.10(19) . . . . ?
C5 C4 C9 C1 179.23(13) . . . . ?
C7 C8 C9 C4 -0.6(2) . . . . ?
C7 C8 C9 C1 -179.63(13) . . . . ?
C2 C1 C9 C4 -1.27(19) . . . . ?
C12 C1 C9 C4 177.56(12) . . . . ?
C2 C1 C9 C8 177.77(13) . . . . ?
C12 C1 C9 C8 -3.4(2) . . . . ?
C6 O4 C10 O3 -7.9(2) . . . . ?
C6 O4 C10 C11 172.14(12) . . . . ?
C2 C1 C12 Se 97.72(13) . . . . ?
C9 C1 C12 Se -81.12(14) . . . . ?
C18 C13 C14 C15 -0.9(2) . . . . ?
Se C13 C14 C15 179.42(11) . . . . ?
C13 C14 C15 C16 -0.3(2) . . . . ?
C14 C15 C16 C17 0.9(2) . . . . ?
C15 C16 C17 C18 -0.4(2) . . . . ?
C14 C13 C18 C17 1.4(2) . . . . ?
Se C13 C18 C17 -178.93(11) . . . . ?
C16 C17 C18 C13 -0.8(2) . . . . ?
