#------------------------------------------------------------------------------
#$Date: 2025-03-04 20:50:56 +0200 (Tue, 04 Mar 2025) $
#$Revision: 298081 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/13/41/7134164.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_7134164
loop_
_publ_author_name
'Mondal, Karunamayee'
'Pilania, Mahima'
'Jayabalan, Karthikeyan'
'Baidya, Mahiuddin'
_publ_section_title
;
 Photoredox cobalt dual catalysis toward C3-functionalization of
 quinoxalinones with alkenes and alkynes.
;
_journal_issue                   12
_journal_name_full               'Chemical communications (Cambridge, England)'
_journal_page_first              2556
_journal_page_last               2559
_journal_paper_doi               10.1039/d4cc05374e
_journal_volume                  61
_journal_year                    2025
_chemical_formula_sum            'C25 H24 N2 O'
_chemical_formula_weight         368.46
_space_group_crystal_system      monoclinic
_space_group_IT_number           14
_space_group_name_Hall           '-P 2yn'
_space_group_name_H-M_alt        'P 1 21/n 1'
_atom_sites_solution_hydrogens   geom
_audit_creation_method           SHELXL-2014/7
_audit_update_record
;
2024-09-19 deposited with the CCDC.	2025-01-09 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 103.941(3)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.2790(7)
_cell_length_b                   10.1279(5)
_cell_length_c                   16.5415(9)
_cell_measurement_reflns_used    4281
_cell_measurement_temperature    296(2)
_cell_measurement_theta_max      24.81
_cell_measurement_theta_min      2.38
_cell_volume                     1996.52(19)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'Bruker SHELXTL'
_computing_publication_material  'Bruker SHELXTL'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-97 (Sheldrick 2008)'
_diffrn_ambient_temperature      296(2)
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 1.000
_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  0.0217
_diffrn_reflns_av_unetI/netI     0.0215
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 1.000
_diffrn_reflns_limit_h_max       14
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       12
_diffrn_reflns_limit_k_min       -12
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -19
_diffrn_reflns_number            14034
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 1.000
_diffrn_reflns_theta_full        24.994
_diffrn_reflns_theta_max         24.994
_diffrn_reflns_theta_min         1.867
_exptl_absorpt_coefficient_mu    0.075
_exptl_absorpt_correction_T_max  0.988
_exptl_absorpt_correction_T_min  0.976
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   'SADABS V2014/5(Bruker AXS.Inc)'
_exptl_crystal_colour            yellow
_exptl_crystal_density_diffrn    1.226
_exptl_crystal_description       Hexagonal
_exptl_crystal_F_000             784
_exptl_crystal_size_max          0.320
_exptl_crystal_size_mid          0.250
_exptl_crystal_size_min          0.160
_refine_diff_density_max         0.178
_refine_diff_density_min         -0.166
_refine_diff_density_rms         0.034
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.014
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     254
_refine_ls_number_reflns         3508
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.014
_refine_ls_R_factor_all          0.0688
_refine_ls_R_factor_gt           0.0450
_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)+(0.0557P)²+0.5666P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1087
_refine_ls_wR_factor_ref         0.1266
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2516
_reflns_number_total             3508
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4cc05374e2.cif
_cod_data_source_block           1417A
_cod_depositor_comments
;
The following automatic conversions were performed:

data item '_exptl_absorpt_correction_type' value 'Multi-scan' was
changed to 'multi-scan' 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 8170 2020-07-09 18:12:32Z antanas 

 Adding full bibliography for 7134164.cif.
;
_cod_original_sg_symbol_H-M      'P 21/n'
_cod_database_code               7134164
_shelx_shelxl_version_number     2014/7
_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   0.976
_shelx_estimated_absorpt_t_max   0.988
loop_
_space_group_symop_operation_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_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
C1 C 0.14665(14) 0.47411(17) 0.01687(10) 0.0421(4) Uani 1 1 d . . . . .
C2 C 0.16651(17) 0.59736(19) -0.01420(12) 0.0563(5) Uani 1 1 d . . . . .
H2 H 0.1704 0.6057 -0.0694 0.068 Uiso 1 1 calc R U . . .
C3 C 0.18033(19) 0.70632(19) 0.03643(13) 0.0621(5) Uani 1 1 d . . . . .
H3 H 0.1935 0.7881 0.0150 0.074 Uiso 1 1 calc R U . . .
C4 C 0.17496(17) 0.69679(18) 0.11848(13) 0.0577(5) Uani 1 1 d . . . . .
H4 H 0.1844 0.7714 0.1522 0.069 Uiso 1 1 calc R U . . .
C5 C 0.15556(16) 0.57609(17) 0.14981(11) 0.0491(5) Uani 1 1 d . . . . .
H5 H 0.1525 0.5692 0.2053 0.059 Uiso 1 1 calc R U . . .
C6 C 0.14044(13) 0.46392(16) 0.10008(10) 0.0385(4) Uani 1 1 d . . . . .
C7 C 0.10447(14) 0.24068(16) 0.08890(10) 0.0396(4) Uani 1 1 d . . . . .
C8 C 0.11186(14) 0.24014(17) 0.00072(11) 0.0444(4) Uani 1 1 d . . . . .
C9 C 0.1425(2) 0.3644(2) -0.11778(12) 0.0708(6) Uani 1 1 d . . . . .
H9A H 0.1311 0.2775 -0.1415 0.106 Uiso 1 1 calc R U . . .
H9B H 0.2159 0.3952 -0.1193 0.106 Uiso 1 1 calc R U . . .
H9C H 0.0869 0.4233 -0.1492 0.106 Uiso 1 1 calc R U . . .
C10 C 0.08113(15) 0.11021(16) 0.12361(11) 0.0456(4) Uani 1 1 d . . . . .
H10A H 0.1452 0.0529 0.1262 0.055 Uiso 1 1 calc R U . . .
H10B H 0.0171 0.0704 0.0854 0.055 Uiso 1 1 calc R U . . .
C11 C 0.05712(14) 0.11581(15) 0.21032(10) 0.0407(4) Uani 1 1 d . . . . .
H11 H 0.1158 0.1701 0.2456 0.049 Uiso 1 1 calc R U . . .
C12 C -0.05460(15) 0.18025(16) 0.20933(10) 0.0401(4) Uani 1 1 d . . . . .
C13 C -0.05894(18) 0.29281(18) 0.25574(11) 0.0530(5) Uani 1 1 d . . . . .
H13 H 0.0072 0.3301 0.2867 0.064 Uiso 1 1 calc R U . . .
C14 C -0.1615(2) 0.3508(2) 0.25658(14) 0.0684(6) Uani 1 1 d . . . . .
H14 H -0.1633 0.4263 0.2883 0.082 Uiso 1 1 calc R U . . .
C15 C -0.2595(2) 0.2974(2) 0.21110(15) 0.0714(7) Uani 1 1 d . . . . .
H15 H -0.3279 0.3365 0.2118 0.086 Uiso 1 1 calc R U . . .
C16 C -0.25656(18) 0.1864(2) 0.16470(14) 0.0652(6) Uani 1 1 d . . . . .
H16 H -0.3231 0.1501 0.1336 0.078 Uiso 1 1 calc R U . . .
C17 C -0.15522(16) 0.12771(18) 0.16367(11) 0.0501(5) Uani 1 1 d . . . . .
H17 H -0.1544 0.0520 0.1320 0.060 Uiso 1 1 calc R U . . .
C18 C 0.06526(15) -0.02245(16) 0.24899(10) 0.0448(4) Uani 1 1 d . . . . .
H18A H 0.0076 -0.0780 0.2151 0.054 Uiso 1 1 calc R U . . .
H18B H 0.1375 -0.0604 0.2481 0.054 Uiso 1 1 calc R U . . .
C19 C 0.05216(16) -0.02355(17) 0.33794(11) 0.0478(4) Uani 1 1 d . . . . .
H19A H 0.1053 0.0387 0.3702 0.057 Uiso 1 1 calc R U . . .
H19B H -0.0226 0.0078 0.3377 0.057 Uiso 1 1 calc R U . . .
C20 C 0.06941(15) -0.15608(18) 0.38171(11) 0.0488(5) Uani 1 1 d . . . . .
C21 C 0.0714(3) -0.1637(3) 0.46479(15) 0.0926(8) Uani 1 1 d . . . . .
H21 H 0.0627 -0.0873 0.4937 0.111 Uiso 1 1 calc R U . . .
C22 C 0.0862(3) -0.2835(4) 0.50631(18) 0.1182(11) Uani 1 1 d . . . . .
H22 H 0.0857 -0.2866 0.5624 0.142 Uiso 1 1 calc R U . . .
C23 C 0.1014(2) -0.3963(3) 0.4665(2) 0.0939(9) Uani 1 1 d . . . . .
H23 H 0.1114 -0.4764 0.4948 0.113 Uiso 1 1 calc R U . . .
C24 C 0.1018(2) -0.3904(2) 0.38569(18) 0.0847(8) Uani 1 1 d . . . . .
H24 H 0.1130 -0.4670 0.3578 0.102 Uiso 1 1 calc R U . . .
C25 C 0.0855(2) -0.27132(19) 0.34331(14) 0.0681(6) Uani 1 1 d . . . . .
H25 H 0.0855 -0.2698 0.2871 0.082 Uiso 1 1 calc R U . . .
N1 N 0.13277(12) 0.35989(14) -0.03093(8) 0.0466(4) Uani 1 1 d . . . . .
N2 N 0.11955(11) 0.34453(13) 0.13521(8) 0.0407(3) Uani 1 1 d . . . . .
O1 O 0.10073(12) 0.13871(13) -0.04072(8) 0.0647(4) 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'
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'
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
N1 C1 C2 123.00(15) . . ?
N1 C1 C6 118.03(14) . . ?
C2 C1 C6 118.96(16) . . ?
C3 C2 C1 120.17(17) . . ?
C3 C2 H2 119.9 . . ?
C1 C2 H2 119.9 . . ?
C2 C3 C4 121.13(18) . . ?
C2 C3 H3 119.4 . . ?
C4 C3 H3 119.4 . . ?
C5 C4 C3 119.26(17) . . ?
C5 C4 H4 120.4 . . ?
C3 C4 H4 120.4 . . ?
C4 C5 C6 121.07(16) . . ?
C4 C5 H5 119.5 . . ?
C6 C5 H5 119.5 . . ?
C5 C6 N2 118.37(14) . . ?
C5 C6 C1 119.39(15) . . ?
N2 C6 C1 122.24(14) . . ?
N2 C7 C8 123.63(15) . . ?
N2 C7 C10 120.44(14) . . ?
C8 C7 C10 115.91(14) . . ?
O1 C8 N1 122.33(15) . . ?
O1 C8 C7 121.93(16) . . ?
N1 C8 C7 115.74(14) . . ?
N1 C9 H9A 109.5 . . ?
N1 C9 H9B 109.5 . . ?
H9A C9 H9B 109.5 . . ?
N1 C9 H9C 109.5 . . ?
H9A C9 H9C 109.5 . . ?
H9B C9 H9C 109.5 . . ?
C7 C10 C11 115.10(13) . . ?
C7 C10 H10A 108.5 . . ?
C11 C10 H10A 108.5 . . ?
C7 C10 H10B 108.5 . . ?
C11 C10 H10B 108.5 . . ?
H10A C10 H10B 107.5 . . ?
C12 C11 C18 111.45(13) . . ?
C12 C11 C10 112.54(14) . . ?
C18 C11 C10 110.41(13) . . ?
C12 C11 H11 107.4 . . ?
C18 C11 H11 107.4 . . ?
C10 C11 H11 107.4 . . ?
C13 C12 C17 118.00(17) . . ?
C13 C12 C11 120.33(16) . . ?
C17 C12 C11 121.66(15) . . ?
C12 C13 C14 120.6(2) . . ?
C12 C13 H13 119.7 . . ?
C14 C13 H13 119.7 . . ?
C15 C14 C13 120.4(2) . . ?
C15 C14 H14 119.8 . . ?
C13 C14 H14 119.8 . . ?
C16 C15 C14 119.7(2) . . ?
C16 C15 H15 120.2 . . ?
C14 C15 H15 120.2 . . ?
C15 C16 C17 120.4(2) . . ?
C15 C16 H16 119.8 . . ?
C17 C16 H16 119.8 . . ?
C16 C17 C12 120.90(19) . . ?
C16 C17 H17 119.6 . . ?
C12 C17 H17 119.6 . . ?
C19 C18 C11 113.56(13) . . ?
C19 C18 H18A 108.9 . . ?
C11 C18 H18A 108.9 . . ?
C19 C18 H18B 108.9 . . ?
C11 C18 H18B 108.9 . . ?
H18A C18 H18B 107.7 . . ?
C20 C19 C18 115.74(14) . . ?
C20 C19 H19A 108.3 . . ?
C18 C19 H19A 108.3 . . ?
C20 C19 H19B 108.3 . . ?
C18 C19 H19B 108.3 . . ?
H19A C19 H19B 107.4 . . ?
C25 C20 C21 116.64(19) . . ?
C25 C20 C19 123.63(17) . . ?
C21 C20 C19 119.73(19) . . ?
C20 C21 C22 121.0(3) . . ?
C20 C21 H21 119.5 . . ?
C22 C21 H21 119.5 . . ?
C23 C22 C21 121.0(3) . . ?
C23 C22 H22 119.5 . . ?
C21 C22 H22 119.5 . . ?
C24 C23 C22 118.8(2) . . ?
C24 C23 H23 120.6 . . ?
C22 C23 H23 120.6 . . ?
C23 C24 C25 120.6(3) . . ?
C23 C24 H24 119.7 . . ?
C25 C24 H24 119.7 . . ?
C20 C25 C24 121.9(2) . . ?
C20 C25 H25 119.1 . . ?
C24 C25 H25 119.1 . . ?
C8 N1 C1 121.92(13) . . ?
C8 N1 C9 117.88(14) . . ?
C1 N1 C9 120.20(14) . . ?
C7 N2 C6 118.40(13) . . ?
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 N1 1.388(2) . ?
C1 C2 1.394(2) . ?
C1 C6 1.401(2) . ?
C2 C3 1.371(3) . ?
C2 H2 0.9300 . ?
C3 C4 1.378(3) . ?
C3 H3 0.9300 . ?
C4 C5 1.371(2) . ?
C4 H4 0.9300 . ?
C5 C6 1.389(2) . ?
C5 H5 0.9300 . ?
C6 N2 1.392(2) . ?
C7 N2 1.288(2) . ?
C7 C8 1.483(2) . ?
C7 C10 1.496(2) . ?
C8 O1 1.224(2) . ?
C8 N1 1.370(2) . ?
C9 N1 1.471(2) . ?
C9 H9A 0.9600 . ?
C9 H9B 0.9600 . ?
C9 H9C 0.9600 . ?
C10 C11 1.533(2) . ?
C10 H10A 0.9700 . ?
C10 H10B 0.9700 . ?
C11 C12 1.516(2) . ?
C11 C18 1.533(2) . ?
C11 H11 0.9800 . ?
C12 C13 1.383(2) . ?
C12 C17 1.389(2) . ?
C13 C14 1.392(3) . ?
C13 H13 0.9300 . ?
C14 C15 1.368(3) . ?
C14 H14 0.9300 . ?
C15 C16 1.367(3) . ?
C15 H15 0.9300 . ?
C16 C17 1.383(3) . ?
C16 H16 0.9300 . ?
C17 H17 0.9300 . ?
C18 C19 1.518(2) . ?
C18 H18A 0.9700 . ?
C18 H18B 0.9700 . ?
C19 C20 1.516(2) . ?
C19 H19A 0.9700 . ?
C19 H19B 0.9700 . ?
C20 C25 1.366(3) . ?
C20 C21 1.371(3) . ?
C21 C22 1.385(4) . ?
C21 H21 0.9300 . ?
C22 C23 1.353(4) . ?
C22 H22 0.9300 . ?
C23 C24 1.339(4) . ?
C23 H23 0.9300 . ?
C24 C25 1.385(3) . ?
C24 H24 0.9300 . ?
C25 H25 0.9300 . ?
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
N1 C1 C2 C3 -179.51(18) . . . . ?
C6 C1 C2 C3 0.4(3) . . . . ?
C1 C2 C3 C4 0.0(3) . . . . ?
C2 C3 C4 C5 0.1(3) . . . . ?
C3 C4 C5 C6 -0.5(3) . . . . ?
C4 C5 C6 N2 -179.16(17) . . . . ?
C4 C5 C6 C1 0.9(3) . . . . ?
N1 C1 C6 C5 179.09(15) . . . . ?
C2 C1 C6 C5 -0.8(3) . . . . ?
N1 C1 C6 N2 -0.9(2) . . . . ?
C2 C1 C6 N2 179.23(16) . . . . ?
N2 C7 C8 O1 177.52(17) . . . . ?
C10 C7 C8 O1 -0.8(3) . . . . ?
N2 C7 C8 N1 -2.0(2) . . . . ?
C10 C7 C8 N1 179.74(15) . . . . ?
N2 C7 C10 C11 10.0(2) . . . . ?
C8 C7 C10 C11 -171.63(15) . . . . ?
C7 C10 C11 C12 69.68(19) . . . . ?
C7 C10 C11 C18 -165.09(15) . . . . ?
C18 C11 C12 C13 115.38(17) . . . . ?
C10 C11 C12 C13 -119.96(16) . . . . ?
C18 C11 C12 C17 -63.4(2) . . . . ?
C10 C11 C12 C17 61.3(2) . . . . ?
C17 C12 C13 C14 0.2(2) . . . . ?
C11 C12 C13 C14 -178.55(16) . . . . ?
C12 C13 C14 C15 -0.3(3) . . . . ?
C13 C14 C15 C16 0.1(3) . . . . ?
C14 C15 C16 C17 0.2(3) . . . . ?
C15 C16 C17 C12 -0.2(3) . . . . ?
C13 C12 C17 C16 0.0(2) . . . . ?
C11 C12 C17 C16 178.79(16) . . . . ?
C12 C11 C18 C19 -58.99(19) . . . . ?
C10 C11 C18 C19 175.16(15) . . . . ?
C11 C18 C19 C20 -174.96(15) . . . . ?
C18 C19 C20 C25 -5.9(3) . . . . ?
C18 C19 C20 C21 172.9(2) . . . . ?
C25 C20 C21 C22 -1.6(4) . . . . ?
C19 C20 C21 C22 179.5(3) . . . . ?
C20 C21 C22 C23 1.3(5) . . . . ?
C21 C22 C23 C24 -0.1(5) . . . . ?
C22 C23 C24 C25 -0.8(4) . . . . ?
C21 C20 C25 C24 0.7(3) . . . . ?
C19 C20 C25 C24 179.5(2) . . . . ?
C23 C24 C25 C20 0.5(4) . . . . ?
O1 C8 N1 C1 -179.18(17) . . . . ?
C7 C8 N1 C1 0.3(2) . . . . ?
O1 C8 N1 C9 -0.3(3) . . . . ?
C7 C8 N1 C9 179.13(16) . . . . ?
C2 C1 N1 C8 -179.12(17) . . . . ?
C6 C1 N1 C8 1.0(2) . . . . ?
C2 C1 N1 C9 2.1(3) . . . . ?
C6 C1 N1 C9 -177.82(16) . . . . ?
C8 C7 N2 C6 2.1(2) . . . . ?
C10 C7 N2 C6 -179.66(15) . . . . ?
C5 C6 N2 C7 179.36(16) . . . . ?
C1 C6 N2 C7 -0.7(2) . . . . ?
