#------------------------------------------------------------------------------
#$Date: 2023-05-05 06:14:58 +0300 (Fri, 05 May 2023) $
#$Revision: 283447 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/15/91/7159196.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_7159196
loop_
_publ_author_name
'Ramkumar, Alagumalai'
'Sreedharan, Ramdas'
'Rajeshwaran, Purushothaman'
'Gandhi, Thirumanavelan'
_publ_section_title
;
 Ruthenium(II)-catalyzed oxidative dehydrogenation and hydroarylation of
 maleimides with phthalazinones - insights into additive-controlled
 product selectivity.
;
_journal_issue                   13
_journal_name_full               'Organic & biomolecular chemistry'
_journal_page_first              2695
_journal_page_last               2699
_journal_paper_doi               10.1039/d3ob00297g
_journal_volume                  21
_journal_year                    2023
_chemical_formula_sum            'C24 H17 N3 O3'
_chemical_formula_weight         395.40
_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   geom
_audit_update_record
;
2022-12-27 deposited with the CCDC.	2023-02-24 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 102.176(2)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   10.4045(9)
_cell_length_b                   8.8690(8)
_cell_length_c                   21.6415(17)
_cell_measurement_reflns_used    9438
_cell_measurement_temperature    300.(2)
_cell_measurement_theta_max      26.73
_cell_measurement_theta_min      2.47
_cell_volume                     1952.1(3)
_computing_cell_refinement       'Bruker SAINT'
_computing_data_collection       'Bruker APEX2'
_computing_data_reduction        'Bruker SAINT'
_computing_molecular_graphics    'shelXle (C.B. Huebschle, rev 1242)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      300.(2)
_diffrn_measured_fraction_theta_full 0.994
_diffrn_measured_fraction_theta_max 0.994
_diffrn_measurement_device_type  'Bruker APEX-II CCD'
_diffrn_measurement_method       'φ and ω scans'
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0574
_diffrn_reflns_av_unetI/netI     0.0425
_diffrn_reflns_limit_h_max       13
_diffrn_reflns_limit_h_min       -11
_diffrn_reflns_limit_k_max       11
_diffrn_reflns_limit_k_min       -11
_diffrn_reflns_limit_l_max       28
_diffrn_reflns_limit_l_min       -28
_diffrn_reflns_number            36983
_diffrn_reflns_theta_full        25.24
_diffrn_reflns_theta_max         28.30
_diffrn_reflns_theta_min         2.47
_exptl_absorpt_coefficient_mu    0.091
_exptl_absorpt_correction_T_max  0.99
_exptl_absorpt_correction_T_min  0.97
_exptl_absorpt_process_details
;
;
_exptl_crystal_colour            colourless
_exptl_crystal_density_diffrn    1.345
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             824
_exptl_crystal_size_max          0.290
_exptl_crystal_size_mid          0.220
_exptl_crystal_size_min          0.140
_refine_diff_density_max         0.150
_refine_diff_density_min         -0.204
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.047
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     271
_refine_ls_number_reflns         4825
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.047
_refine_ls_R_factor_all          0.1012
_refine_ls_R_factor_gt           0.0501
_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)+(0.0388P)²+0.5941P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1004
_refine_ls_wR_factor_ref         0.1224
_reflns_Friedel_coverage         0.000
_reflns_number_gt                2949
_reflns_number_total             4825
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d3ob00297g2.cif
_cod_data_source_block           Alkane_3
_cod_depositor_comments
'Adding full bibliography for 7159195--7159196.cif.'
_cod_database_code               7159196
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_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_refinement_flags_adp
_atom_site_refinement_flags_occupancy
_atom_site_refinement_flags_posn
_atom_site_occupancy
_atom_site_disorder_assembly
_atom_site_disorder_group
O O1 0.42439(16) 0.29268(17) 0.39161(7) 0.0753(4) Uani d . . . 1 . .
O O2 0.49030(12) 0.64194(15) 0.24753(6) 0.0598(4) Uani d . . . 1 . .
O O4 0.10130(14) 0.56176(15) 0.33540(7) 0.0647(4) Uani d . . . 1 . .
N N1 0.28877(15) 0.85615(16) 0.28643(7) 0.0502(4) Uani d . . . 1 . .
N N2 0.47932(14) 0.48342(16) 0.33024(7) 0.0449(4) Uani d . . . 1 . .
N N4 0.21554(13) 0.72544(15) 0.28809(6) 0.0419(3) Uani d . . . 1 . .
C C1 0.04997(18) 0.7446(2) 0.19238(9) 0.0561(5) Uani d . . . 1 . .
H H1 0.021714 0.832039 0.209154 0.067000 Uiso calc U . R 1 . .
C C2 -0.0150(2) 0.6939(3) 0.13418(10) 0.0668(6) Uani d . . . 1 . .
H H2 -0.087801 0.745658 0.111758 0.080000 Uiso calc U . R 1 . .
C C3 0.0286(2) 0.5665(3) 0.10963(10) 0.0699(6) Uani d . . . 1 . .
H H3 -0.015413 0.530773 0.070469 0.084000 Uiso calc U . R 1 . .
C C4 0.1377(2) 0.4902(2) 0.14251(9) 0.0580(5) Uani d . . . 1 . .
H H4 0.166716 0.404618 0.124714 0.070000 Uiso calc U . R 1 . .
C C5 0.20500(16) 0.53879(19) 0.20166(8) 0.0425(4) Uani d . . . 1 . .
C C6 0.32793(19) 0.9250(2) 0.33932(9) 0.0530(5) Uani d . . . 1 . .
H H6 0.378914 1.011082 0.339158 0.064000 Uiso calc U . R 1 . .
C C7 0.29923(17) 0.87967(19) 0.39844(8) 0.0444(4) Uani d . . . 1 . .
C C8 0.22396(16) 0.75078(18) 0.39953(8) 0.0428(4) Uani d . . . 1 . .
C C9 0.17439(17) 0.67062(19) 0.34008(9) 0.0452(4) Uani d . . . 1 . .
C C10 0.32143(16) 0.44767(19) 0.23604(8) 0.0451(4) Uani d . . . 1 . .
H H10 0.351515 0.386120 0.204246 0.054000 Uiso calc U . R 1 . .
C C11 0.29380(17) 0.3399(2) 0.28684(9) 0.0519(5) Uani d . . . 1 . .
H H11A 0.209864 0.363077 0.297377 0.062000 Uiso calc U . R 1 . .
H H11B 0.292098 0.236347 0.272287 0.062000 Uiso calc U . R 1 . .
C C12 0.40258(19) 0.3628(2) 0.34243(9) 0.0509(5) Uani d . . . 1 . .
C C13 0.43795(16) 0.5399(2) 0.26934(8) 0.0441(4) Uani d . . . 1 . .
C C14 0.3427(2) 0.9609(2) 0.45440(10) 0.0598(5) Uani d . . . 1 . .
H H14 0.391346 1.048786 0.454189 0.072000 Uiso calc U . R 1 . .
C C15 0.3130(2) 0.9097(3) 0.50967(10) 0.0690(6) Uani d . . . 1 . .
H H15 0.341707 0.963110 0.546998 0.083000 Uiso calc U . R 1 . .
C C16 0.2407(2) 0.7793(3) 0.51004(10) 0.0685(6) Uani d . . . 1 . .
H H16 0.223162 0.744215 0.547905 0.082000 Uiso calc U . R 1 . .
C C17 0.19456(19) 0.7008(2) 0.45529(9) 0.0563(5) Uani d . . . 1 . .
H H17 0.143876 0.614554 0.455742 0.068000 Uiso calc U . R 1 . .
C C18 0.59343(17) 0.53775(19) 0.37389(8) 0.0455(4) Uani d . . . 1 . .
C C19 0.5812(2) 0.5986(2) 0.43110(9) 0.0595(5) Uani d . . . 1 . .
H H19 0.499309 0.604275 0.441749 0.071000 Uiso calc U . R 1 . .
C C20 0.6925(2) 0.6511(2) 0.47245(10) 0.0679(6) Uani d . . . 1 . .
H H20 0.685355 0.692192 0.511126 0.081000 Uiso calc U . R 1 . .
C C21 0.8134(2) 0.6425(2) 0.45642(10) 0.0663(6) Uani d . . . 1 . .
H H21 0.887788 0.678353 0.484182 0.080000 Uiso calc U . R 1 . .
C C22 0.8245(2) 0.5813(2) 0.39974(10) 0.0618(5) Uani d . . . 1 . .
H H22 0.906463 0.575211 0.389175 0.074000 Uiso calc U . R 1 . .
C C23 0.71437(18) 0.5285(2) 0.35819(9) 0.0523(5) Uani d . . . 1 . .
H H23 0.722057 0.486845 0.319697 0.063000 Uiso calc U . R 1 . .
C C25 0.15701(16) 0.66666(19) 0.22622(8) 0.0418(4) Uani d . . . 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'
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_site_symmetry_1
_geom_angle_site_symmetry_3
_geom_angle
_geom_angle_publ_flag
C6 N1 N4 . . 116.44(14) ?
C13 N2 C12 . . 112.40(15) ?
C13 N2 C18 . . 123.40(14) ?
C12 N2 C18 . . 124.09(15) ?
C9 N4 N1 . . 125.62(14) ?
C9 N4 C25 . . 119.17(14) ?
N1 N4 C25 . . 113.73(13) ?
C2 C1 C25 . . 120.53(18) ?
C3 C2 C1 . . 119.18(19) ?
C2 C3 C4 . . 120.6(2) ?
C3 C4 C5 . . 121.41(19) ?
C25 C5 C4 . . 116.93(16) ?
C25 C5 C10 . . 124.22(16) ?
C4 C5 C10 . . 118.81(16) ?
N1 C6 C7 . . 125.15(17) ?
C8 C7 C14 . . 119.31(17) ?
C8 C7 C6 . . 118.11(16) ?
C14 C7 C6 . . 122.58(17) ?
C17 C8 C7 . . 120.63(17) ?
C17 C8 C9 . . 120.68(16) ?
C7 C8 C9 . . 118.67(15) ?
O4 C9 N4 . . 120.55(17) ?
O4 C9 C8 . . 123.69(16) ?
N4 C9 C8 . . 115.76(15) ?
C13 C10 C5 . . 115.02(14) ?
C13 C10 C11 . . 104.40(14) ?
C5 C10 C11 . . 115.76(14) ?
C12 C11 C10 . . 105.73(14) ?
O1 C12 N2 . . 123.48(18) ?
O1 C12 C11 . . 127.77(17) ?
N2 C12 C11 . . 108.74(15) ?
O2 C13 N2 . . 124.59(17) ?
O2 C13 C10 . . 127.12(16) ?
N2 C13 C10 . . 108.26(14) ?
C15 C14 C7 . . 119.47(19) ?
C14 C15 C16 . . 120.3(2) ?
C17 C16 C15 . . 120.8(2) ?
C16 C17 C8 . . 119.40(19) ?
C23 C18 C19 . . 120.50(18) ?
C23 C18 N2 . . 119.40(16) ?
C19 C18 N2 . . 120.10(16) ?
C18 C19 C20 . . 119.22(19) ?
C21 C20 C19 . . 120.14(19) ?
C22 C21 C20 . . 120.2(2) ?
C21 C22 C23 . . 120.21(19) ?
C18 C23 C22 . . 119.76(18) ?
C1 C25 C5 . . 121.33(16) ?
C1 C25 N4 . . 116.44(15) ?
C5 C25 N4 . . 122.23(15) ?
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
O1 C12 . 1.212(2) ?
O2 C13 . 1.203(2) ?
O4 C9 . 1.220(2) ?
N1 C6 . 1.285(2) ?
N1 N4 . 1.3919(19) ?
N2 C13 . 1.391(2) ?
N2 C12 . 1.393(2) ?
N2 C18 . 1.436(2) ?
N4 C9 . 1.374(2) ?
N4 C25 . 1.446(2) ?
C1 C2 . 1.373(3) ?
C1 C25 . 1.382(2) ?
C2 C3 . 1.366(3) ?
C3 C4 . 1.382(3) ?
C4 C5 . 1.392(2) ?
C5 C25 . 1.389(2) ?
C5 C10 . 1.515(2) ?
C6 C7 . 1.432(2) ?
C7 C8 . 1.389(2) ?
C7 C14 . 1.400(3) ?
C8 C17 . 1.379(2) ?
C8 C9 . 1.465(2) ?
C10 C13 . 1.513(2) ?
C10 C11 . 1.529(2) ?
C11 C12 . 1.482(3) ?
C14 C15 . 1.374(3) ?
C15 C16 . 1.380(3) ?
C16 C17 . 1.371(3) ?
C18 C23 . 1.373(2) ?
C18 C19 . 1.381(2) ?
C19 C20 . 1.386(3) ?
C20 C21 . 1.376(3) ?
C21 C22 . 1.368(3) ?
C22 C23 . 1.381(3) ?
