#------------------------------------------------------------------------------
#$Date: 2023-02-21 13:11:38 +0200 (Tue, 21 Feb 2023) $
#$Revision: 281063 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/24/63/7246314.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_7246314
loop_
_publ_author_name
'Lalji, Ram Sunil Kumar'
Prince,
'Gupta, Mohit'
'Kumar, Sandeep'
'Kumar, Amit'
'Singh, Brajendra Kumar'
_publ_section_title
;
 Rhodium-catalyzed selenylation and sulfenylation of quinoxalinones
 ‘on water’
;
_journal_issue                   9
_journal_name_full               'RSC Advances'
_journal_page_first              6191
_journal_page_last               6198
_journal_paper_doi               10.1039/D2RA07400A
_journal_volume                  13
_journal_year                    2023
_chemical_formula_moiety         'C22 H17 F N2 O Se'
_chemical_formula_sum            'C22 H17 F N2 O Se'
_chemical_formula_weight         423.33
_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
_audit_creation_method           SHELXL-2018/3
_audit_update_record
;
2022-10-24 deposited with the CCDC.	2023-02-08 downloaded from the CCDC.
;
_cell_angle_alpha                99.181(5)
_cell_angle_beta                 91.413(5)
_cell_angle_gamma                114.770(7)
_cell_formula_units_Z            4
_cell_length_a                   9.8962(7)
_cell_length_b                   10.3482(6)
_cell_length_c                   21.7111(10)
_cell_measurement_reflns_used    6978
_cell_measurement_temperature    298(2)
_cell_measurement_theta_max      23.9560
_cell_measurement_theta_min      3.140
_cell_volume                     1982.6(2)
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      298(2)
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.848
_diffrn_measurement_device_type  'SuperNova, Dual, Cu at home/near, Eos'
_diffrn_measurement_method       'ω scans'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0711
_diffrn_reflns_av_unetI/netI     0.1052
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.848
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -13
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -13
_diffrn_reflns_limit_l_max       27
_diffrn_reflns_limit_l_min       -27
_diffrn_reflns_number            20772
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.848
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         29.225
_diffrn_reflns_theta_min         3.120
_diffrn_source                   'micro-focus sealed X-ray tube'
_exptl_absorpt_coefficient_mu    1.916
_exptl_absorpt_correction_type   none
_exptl_crystal_colour            PALE-YELLOW
_exptl_crystal_density_diffrn    1.418
_exptl_crystal_description       BLOCK
_exptl_crystal_F_000             856
_exptl_crystal_size_max          0.210
_exptl_crystal_size_mid          0.190
_exptl_crystal_size_min          0.180
_refine_diff_density_max         0.558
_refine_diff_density_min         -0.605
_refine_diff_density_rms         0.070
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.017
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     489
_refine_ls_number_reflns         9130
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.017
_refine_ls_R_factor_all          0.1233
_refine_ls_R_factor_gt           0.0539
_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)+(0.0306P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0935
_refine_ls_wR_factor_ref         0.1266
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4826
_reflns_number_total             9130
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2ra07400a2.cif
_cod_data_source_block           Compound_3c
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'NONE' was changed
to 'none' in accordance with the
/home/data/users/saulius/crontab/automatic-downloads/rss-feeds/RSC/lib/dictionaries/cif_core.dic
dictionary named 'cif_core.dic' version 2.4.2 last updated on
2011-04-26.

Automatic conversion script
Id: cif_fix_values 7556 2019-12-06 15:28:31Z antanas 
;
_cod_database_code               7246314
_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   0.689
_shelx_estimated_absorpt_t_max   0.724
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
Se1 Se 0.46231(5) 0.11600(4) 0.25267(2) 0.05692(15) Uani 1 1 d . . . . .
Se2 Se 0.22647(5) 1.06781(4) 0.67351(2) 0.05818(16) Uani 1 1 d . . . . .
N1 N 0.1018(4) 0.7749(3) 0.59515(15) 0.0484(8) Uani 1 1 d . . . . .
F2 F 0.2607(4) 0.1460(3) 0.51540(13) 0.1030(11) Uani 1 1 d . . . . .
O1 O 0.1678(4) 0.5492(3) 0.69081(15) 0.0772(10) Uani 1 1 d . . . . .
N3 N 0.4794(4) 0.0642(3) 0.12207(15) 0.0551(9) Uani 1 1 d . . . . .
F1 F 0.6038(4) 1.5886(3) 0.87545(14) 0.1285(13) Uani 1 1 d . . . . .
N2 N 0.1924(4) 0.5483(3) 0.58563(18) 0.0602(10) Uani 1 1 d . . . . .
N4 N 0.3561(5) 0.1152(4) 0.01524(15) 0.0603(10) Uani 1 1 d . . . . .
O2 O 0.1217(4) -0.0274(4) 0.04050(14) 0.0866(10) Uani 1 1 d . . . . .
C16 C 0.1088(4) 0.9289(4) 0.72428(17) 0.0485(10) Uani 1 1 d . . . . .
C11 C 0.0652(4) 0.7780(4) 0.70466(17) 0.0437(9) Uani 1 1 d . . . . .
C10 C 0.1079(4) 0.7189(4) 0.64428(18) 0.0464(10) Uani 1 1 d . . . . .
C17 C 0.3392(5) 1.2305(4) 0.74122(18) 0.0508(10) Uani 1 1 d . . . . .
C27 C 0.5704(5) 0.1572(4) 0.0849(2) 0.0531(11) Uani 1 1 d . . . . .
C5 C 0.1432(5) 0.7220(4) 0.53837(19) 0.0537(11) Uani 1 1 d . . . . .
C32 C 0.3349(5) 0.0025(4) 0.10782(18) 0.0512(11) Uani 1 1 d . . . . .
C39 C 0.3985(5) 0.1283(4) 0.33662(19) 0.0537(11) Uani 1 1 d . . . . .
C33 C 0.2424(5) -0.0940(4) 0.14920(18) 0.0489(10) Uani 1 1 d . . . . .
C44 C 0.4790(5) 0.1105(4) 0.3859(2) 0.0588(12) Uani 1 1 d . . . . .
H44 H 0.561816 0.091754 0.378502 0.071 Uiso 1 1 calc R U . . .
C31 C 0.2602(6) 0.0259(5) 0.0521(2) 0.0600(12) Uani 1 1 d . . . . .
C37 C 0.2090(5) -0.1608(4) 0.2526(2) 0.0613(12) Uani 1 1 d . . . . .
H37 H 0.241503 -0.142074 0.294995 0.074 Uiso 1 1 calc R U . . .
C38 C 0.2900(5) -0.0621(4) 0.21509(19) 0.0505(11) Uani 1 1 d . . . . .
C15 C 0.0630(5) 0.9780(5) 0.78050(19) 0.0583(12) Uani 1 1 d . . . . .
H15 H 0.091863 1.076689 0.793552 0.070 Uiso 1 1 calc R U . . .
C9 C 0.1585(5) 0.6000(4) 0.6435(2) 0.0560(12) Uani 1 1 d . . . . .
C12 C -0.0231(5) 0.6829(5) 0.7423(2) 0.0621(12) Uani 1 1 d . . . . .
H12 H -0.051234 0.584052 0.730175 0.074 Uiso 1 1 calc R U . . .
C28 C 0.5118(5) 0.1852(4) 0.0312(2) 0.0566(11) Uani 1 1 d . . . . .
C6 C 0.1885(5) 0.6093(4) 0.5325(2) 0.0590(12) Uani 1 1 d . . . . .
C34 C 0.1110(5) -0.2208(4) 0.1260(2) 0.0641(13) Uani 1 1 d . . . . .
H34 H 0.076838 -0.241370 0.083730 0.077 Uiso 1 1 calc R U . . .
C4 C 0.1358(5) 0.7861(5) 0.4863(2) 0.0704(14) Uani 1 1 d . . . . .
H4 H 0.105041 0.860281 0.490638 0.085 Uiso 1 1 calc R U . . .
C42 C 0.3081(6) 0.1429(4) 0.4561(2) 0.0678(14) Uani 1 1 d . . . . .
C43 C 0.4341(6) 0.1212(4) 0.4463(2) 0.0657(13) Uani 1 1 d . . . . .
H43 H 0.489333 0.113569 0.479642 0.079 Uiso 1 1 calc R U . . .
C40 C 0.2709(5) 0.1530(4) 0.3480(2) 0.0661(13) Uani 1 1 d . . . . .
H40 H 0.217567 0.164940 0.315164 0.079 Uiso 1 1 calc R U . . .
C36 C 0.0817(6) -0.2856(5) 0.2283(2) 0.0727(14) Uani 1 1 d . . . . .
H36 H 0.029768 -0.349371 0.254236 0.087 Uiso 1 1 calc R U . . .
C14 C -0.0244(5) 0.8819(5) 0.8169(2) 0.0660(13) Uani 1 1 d . . . . .
H14 H -0.052926 0.916302 0.854143 0.079 Uiso 1 1 calc R U . . .
C26 C 0.7258(6) 0.2237(5) 0.1025(2) 0.0674(13) Uani 1 1 d . . . . .
H26 H 0.763927 0.204347 0.137689 0.081 Uiso 1 1 calc R U . . .
C35 C 0.0314(6) -0.3155(4) 0.1643(3) 0.0751(15) Uani 1 1 d . . . . .
H35 H -0.054858 -0.398228 0.147741 0.090 Uiso 1 1 calc R U . . .
C18 C 0.3122(6) 1.3528(4) 0.7504(2) 0.0714(14) Uani 1 1 d . . . . .
H18 H 0.234235 1.354235 0.726201 0.086 Uiso 1 1 calc R U . . .
C29 C 0.2857(6) 0.1357(5) -0.0422(2) 0.0792(15) Uani 1 1 d . . . . .
H29A H 0.190587 0.052525 -0.055747 0.095 Uiso 1 1 calc R U . . .
H29B H 0.349849 0.140913 -0.075653 0.095 Uiso 1 1 calc R U . . .
C7 C 0.2392(5) 0.4273(4) 0.5827(2) 0.0745(15) Uani 1 1 d . . . . .
H7A H 0.208081 0.367353 0.541175 0.089 Uiso 1 1 calc R U . . .
H7B H 0.188455 0.367463 0.612597 0.089 Uiso 1 1 calc R U . . .
C20 C 0.5152(6) 1.4698(5) 0.8306(2) 0.0772(16) Uani 1 1 d . . . . .
C41 C 0.2236(6) 0.1597(5) 0.4081(3) 0.0751(14) Uani 1 1 d . . . . .
H41 H 0.138829 0.174837 0.415805 0.090 Uiso 1 1 calc R U . . .
C13 C -0.0696(5) 0.7330(5) 0.7973(2) 0.0699(13) Uani 1 1 d . . . . .
H13 H -0.130453 0.667859 0.820870 0.084 Uiso 1 1 calc R U . . .
C22 C 0.4566(6) 1.2307(5) 0.7774(2) 0.0795(15) Uani 1 1 d . . . . .
H22 H 0.476452 1.149572 0.771391 0.095 Uiso 1 1 calc R U . . .
C23 C 0.6103(7) 0.2827(5) -0.0032(2) 0.0756(15) Uani 1 1 d . . . . .
H23 H 0.573198 0.304228 -0.038082 0.091 Uiso 1 1 calc R U . . .
C25 C 0.8219(6) 0.3172(5) 0.0678(3) 0.0799(16) Uani 1 1 d . . . . .
H25 H 0.924518 0.360138 0.079300 0.096 Uiso 1 1 calc R U . . .
C24 C 0.7640(7) 0.3472(5) 0.0151(3) 0.0843(17) Uani 1 1 d . . . . .
H24 H 0.828737 0.410878 -0.008056 0.101 Uiso 1 1 calc R U . . .
C3 C 0.1739(6) 0.7391(6) 0.4287(2) 0.0943(19) Uani 1 1 d . . . . .
H3 H 0.168414 0.780395 0.394272 0.113 Uiso 1 1 calc R U . . .
C8 C 0.4087(6) 0.4814(5) 0.5970(3) 0.0964(19) Uani 1 1 d . . . . .
H8A H 0.459747 0.541450 0.567818 0.145 Uiso 1 1 calc R U . . .
H8B H 0.432874 0.399978 0.593245 0.145 Uiso 1 1 calc R U . . .
H8C H 0.439507 0.536574 0.638924 0.145 Uiso 1 1 calc R U . . .
C1 C 0.2295(6) 0.5635(5) 0.4736(3) 0.0825(17) Uani 1 1 d . . . . .
H1 H 0.261763 0.490312 0.468846 0.099 Uiso 1 1 calc R U . . .
C21 C 0.5458(6) 1.3519(6) 0.8229(2) 0.0844(16) Uani 1 1 d . . . . .
H21 H 0.624278 1.351865 0.847318 0.101 Uiso 1 1 calc R U . . .
C19 C 0.4009(7) 1.4741(5) 0.7958(3) 0.0878(17) Uani 1 1 d . . . . .
H19 H 0.382389 1.555974 0.802099 0.105 Uiso 1 1 calc R U . . .
C30 C 0.2603(7) 0.2729(6) -0.0305(2) 0.1020(19) Uani 1 1 d . . . . .
H30A H 0.192963 0.266215 0.001196 0.153 Uiso 1 1 calc R U . . .
H30B H 0.217991 0.283247 -0.068626 0.153 Uiso 1 1 calc R U . . .
H30C H 0.354099 0.355536 -0.016674 0.153 Uiso 1 1 calc R U . . .
C2 C 0.2213(7) 0.6274(7) 0.4237(3) 0.101(2) Uani 1 1 d . . . . .
H2 H 0.247958 0.595908 0.385364 0.121 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'
F F 0.0171 0.0103 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
N N 0.0061 0.0033 '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
C39 Se1 C38 96.45(17) . . ?
C17 Se2 C16 98.38(16) . . ?
C10 N1 C5 118.9(3) . . ?
C32 N3 C27 119.3(4) . . ?
C9 N2 C6 122.0(3) . . ?
C9 N2 C7 116.9(4) . . ?
C6 N2 C7 121.1(3) . . ?
C31 N4 C28 122.0(4) . . ?
C31 N4 C29 116.9(4) . . ?
C28 N4 C29 121.1(4) . . ?
C15 C16 C11 119.2(4) . . ?
C15 C16 Se2 119.6(3) . . ?
C11 C16 Se2 121.1(3) . . ?
C12 C11 C16 118.5(3) . . ?
C12 C11 C10 119.9(3) . . ?
C16 C11 C10 121.6(3) . . ?
N1 C10 C11 118.2(3) . . ?
N1 C10 C9 123.1(4) . . ?
C11 C10 C9 118.7(3) . . ?
C18 C17 C22 118.9(4) . . ?
C18 C17 Se2 120.7(3) . . ?
C22 C17 Se2 120.2(3) . . ?
N3 C27 C26 117.6(4) . . ?
N3 C27 C28 122.3(4) . . ?
C26 C27 C28 120.1(4) . . ?
C6 C5 N1 122.3(4) . . ?
C6 C5 C4 120.5(4) . . ?
N1 C5 C4 117.2(4) . . ?
N3 C32 C33 117.5(4) . . ?
N3 C32 C31 122.8(4) . . ?
C33 C32 C31 119.7(4) . . ?
C44 C39 C40 119.8(4) . . ?
C44 C39 Se1 119.6(3) . . ?
C40 C39 Se1 120.6(3) . . ?
C34 C33 C38 117.9(4) . . ?
C34 C33 C32 122.5(4) . . ?
C38 C33 C32 119.6(3) . . ?
C43 C44 C39 119.5(4) . . ?
O2 C31 N4 121.8(4) . . ?
O2 C31 C32 122.6(5) . . ?
N4 C31 C32 115.6(4) . . ?
C36 C37 C38 121.8(4) . . ?
C37 C38 C33 118.9(4) . . ?
C37 C38 Se1 120.0(3) . . ?
C33 C38 Se1 121.1(3) . . ?
C14 C15 C16 121.2(4) . . ?
O1 C9 N2 121.6(4) . . ?
O1 C9 C10 123.0(4) . . ?
N2 C9 C10 115.4(4) . . ?
C13 C12 C11 121.6(4) . . ?
N4 C28 C23 123.1(5) . . ?
N4 C28 C27 117.9(4) . . ?
C23 C28 C27 119.0(5) . . ?
C5 C6 N2 118.2(4) . . ?
C5 C6 C1 118.5(5) . . ?
N2 C6 C1 123.2(4) . . ?
C35 C34 C33 122.1(4) . . ?
C3 C4 C5 120.5(5) . . ?
C43 C42 F2 119.1(5) . . ?
C43 C42 C41 122.6(5) . . ?
F2 C42 C41 118.3(5) . . ?
C42 C43 C44 119.7(4) . . ?
C41 C40 C39 120.7(4) . . ?
C37 C36 C35 119.7(4) . . ?
C15 C14 C13 119.8(4) . . ?
C25 C26 C27 120.4(5) . . ?
C34 C35 C36 119.5(4) . . ?
C17 C18 C19 120.7(5) . . ?
N4 C29 C30 112.3(3) . . ?
N2 C7 C8 112.9(3) . . ?
C21 C20 C19 122.5(4) . . ?
C21 C20 F1 118.2(6) . . ?
C19 C20 F1 119.3(5) . . ?
C40 C41 C42 117.7(5) . . ?
C12 C13 C14 119.7(4) . . ?
C17 C22 C21 120.6(4) . . ?
C24 C23 C28 119.8(5) . . ?
C26 C25 C24 119.6(5) . . ?
C23 C24 C25 121.0(5) . . ?
C4 C3 C2 118.4(5) . . ?
C2 C1 C6 119.9(5) . . ?
C20 C21 C22 118.6(5) . . ?
C20 C19 C18 118.6(4) . . ?
C1 C2 C3 122.1(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
Se1 C39 1.946(4) . ?
Se1 C38 1.947(4) . ?
Se2 C17 1.948(4) . ?
Se2 C16 1.951(4) . ?
N1 C10 1.304(5) . ?
N1 C5 1.409(5) . ?
F2 C42 1.381(5) . ?
O1 C9 1.245(5) . ?
N3 C32 1.303(5) . ?
N3 C27 1.396(5) . ?
F1 C20 1.379(5) . ?
N2 C9 1.391(5) . ?
N2 C6 1.407(5) . ?
N2 C7 1.499(5) . ?
N4 C31 1.390(5) . ?
N4 C28 1.406(5) . ?
N4 C29 1.500(5) . ?
O2 C31 1.245(5) . ?
C16 C15 1.405(5) . ?
C16 C11 1.422(5) . ?
C11 C12 1.404(5) . ?
C11 C10 1.503(5) . ?
C10 C9 1.508(5) . ?
C17 C18 1.384(5) . ?
C17 C22 1.385(6) . ?
C27 C26 1.409(6) . ?
C27 C28 1.413(6) . ?
C5 C6 1.403(6) . ?
C5 C4 1.415(6) . ?
C32 C33 1.484(5) . ?
C32 C31 1.506(6) . ?
C39 C44 1.399(5) . ?
C39 C40 1.410(6) . ?
C33 C34 1.412(5) . ?
C33 C38 1.436(5) . ?
C44 C43 1.397(6) . ?
C37 C36 1.386(6) . ?
C37 C38 1.400(5) . ?
C15 C14 1.387(6) . ?
C12 C13 1.391(5) . ?
C28 C23 1.407(6) . ?
C6 C1 1.421(6) . ?
C34 C35 1.384(6) . ?
C4 C3 1.387(6) . ?
C42 C43 1.373(7) . ?
C42 C41 1.398(6) . ?
C40 C41 1.398(6) . ?
C36 C35 1.405(6) . ?
C14 C13 1.400(6) . ?
C26 C25 1.380(6) . ?
C18 C19 1.398(6) . ?
C29 C30 1.526(6) . ?
C7 C8 1.535(6) . ?
C20 C21 1.362(7) . ?
C20 C19 1.365(7) . ?
C22 C21 1.400(6) . ?
C23 C24 1.397(7) . ?
C25 C24 1.401(7) . ?
C3 C2 1.409(8) . ?
C1 C2 1.374(7) . ?
