#------------------------------------------------------------------------------
#$Date: 2023-03-04 20:34:15 +0200 (Sat, 04 Mar 2023) $
#$Revision: 281527 $
#$URL: file:///home/coder/svn-repositories/cod/cif/7/06/21/7062173.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_7062173
loop_
_publ_author_name
'Ohira, Kazuki'
'Yamamoto, Masahiro'
'Imato, Keiichi'
'Ooyama, Yousuke'
_publ_section_title
;
 Synthesis and optical properties of phenazinone-based photosensitizers
 for singlet oxygen generation
;
_journal_issue                   6
_journal_name_full               'New Journal of Chemistry'
_journal_page_first              2711
_journal_page_last               2718
_journal_paper_doi               10.1039/D2NJ05322E
_journal_volume                  47
_journal_year                    2023
_chemical_formula_sum            'C20 H13 Cl N2 O3'
_chemical_formula_weight         364.77
_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_block_doi                 10.5517/ccdc.csd.cc2cnx10
_audit_update_record
;
2022-08-04 deposited with the CCDC.	2022-12-18 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 93.9830(10)
_cell_angle_gamma                90
_cell_formula_units_Z            4
_cell_length_a                   12.9125(8)
_cell_length_b                   17.0395(10)
_cell_length_c                   7.2712(4)
_cell_measurement_reflns_used    12633
_cell_measurement_temperature    100.(2)
_cell_measurement_theta_max      28.9899
_cell_measurement_theta_min      1.9387
_cell_volume                     1595.96(16)
_computing_data_collection       'APEX2(Bruker AXS)'
_computing_molecular_graphics    'XSHELL V6.3.1(Bruker AXS)'
_computing_publication_material  'Generate Report (Bruker AXS)'
_computing_structure_refinement  'SHELXL-2018/3 (Sheldrick, 2018)'
_computing_structure_solution    'SHELXT 2018/2 (Sheldrick, 2018)'
_diffrn_ambient_temperature      100.(2)
_diffrn_detector_area_resol_mean 8.3333
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.998
_diffrn_measurement_device_type  'Bruker D8 goniometer'
_diffrn_measurement_method       'omega scans'
_diffrn_radiation_monochromator  'multilayered confocal mirror'
_diffrn_radiation_type           MoKa
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0202
_diffrn_reflns_av_unetI/netI     0.0157
_diffrn_reflns_limit_h_max       17
_diffrn_reflns_limit_h_min       -16
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -22
_diffrn_reflns_limit_l_max       9
_diffrn_reflns_limit_l_min       -9
_diffrn_reflns_number            18708
_diffrn_reflns_theta_full        27.93
_diffrn_reflns_theta_max         27.93
_diffrn_reflns_theta_min         1.98
_diffrn_source                   'rotating-anode X-ray tube'
_diffrn_source_type              'Bruker Turbo X-ray Source'
_exptl_absorpt_coefficient_mu    0.264
_exptl_absorpt_correction_T_max  0.98
_exptl_absorpt_correction_T_min  0.96
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2016/2 - Bruker AXS area detector scaling and absorption correction
;
_exptl_crystal_colour            'clear red'
_exptl_crystal_density_diffrn    1.518
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       block
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.170
_exptl_crystal_size_mid          0.140
_exptl_crystal_size_min          0.080
_refine_diff_density_max         0.359
_refine_diff_density_min         -0.281
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.025
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     236
_refine_ls_number_reflns         3827
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.025
_refine_ls_R_factor_all          0.0410
_refine_ls_R_factor_gt           0.0341
_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)+(0.0484P)²+0.6591P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0887
_refine_ls_wR_factor_ref         0.0935
_reflns_number_gt                3316
_reflns_number_total             3827
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2nj05322e2.cif
_cod_data_source_block           20210603NMeBenzoyl_cif
_cod_depositor_comments
'Adding full bibliography for 7062171--7062173.cif.'
_cod_database_code               7062173
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
C C2 0.34440(9) 0.49893(7) 0.78326(17) 0.0195(2) Uani d . . . 1 . .
C C3 0.24368(9) 0.50811(7) 0.67450(17) 0.0193(2) Uani d . . . 1 . .
C C4 0.20355(9) 0.57764(8) 0.62382(17) 0.0203(3) Uani d . . . 1 . .
H H3 0.137246 0.580282 0.558782 0.024 Uiso calc U . R 1 . .
C C5 0.26052(9) 0.64870(7) 0.66746(16) 0.0178(2) Uani d . . . 1 . .
C C6 0.26865(10) 0.78347(7) 0.67377(17) 0.0193(2) Uani d . . . 1 . .
C C7 0.21696(10) 0.85566(8) 0.64429(18) 0.0235(3) Uani d . . . 1 . .
H H6 0.147785 0.856275 0.590473 0.028 Uiso calc U . R 1 . .
C C8 0.26530(11) 0.92496(8) 0.69235(19) 0.0263(3) Uani d . . . 1 . .
H H7 0.229789 0.973397 0.672924 0.032 Uiso calc U . R 1 . .
C C9 0.36790(11) 0.92377(8) 0.77065(19) 0.0257(3) Uani d . . . 1 . .
H H8 0.401137 0.971877 0.804635 0.031 Uiso calc U . R 1 . .
C C10 0.42131(10) 0.85442(8) 0.79918(18) 0.0226(3) Uani d . . . 1 . .
H H9 0.490855 0.855042 0.851202 0.027 Uiso calc U . R 1 . .
C C11 0.37281(9) 0.78258(7) 0.75124(16) 0.0185(2) Uani d . . . 1 . .
C C12 0.53078(9) 0.70425(8) 0.84159(18) 0.0226(3) Uani d . . . 1 . .
H H11A 0.537015 0.688574 0.971557 0.034 Uiso calc U . R 1 . .
H H11B 0.564386 0.755282 0.827788 0.034 Uiso calc U . R 1 . .
H H11C 0.564512 0.664948 0.767579 0.034 Uiso calc U . R 1 . .
C C13 0.36584(9) 0.64104(7) 0.75428(16) 0.0170(2) Uani d . . . 1 . .
C C1 0.40532(9) 0.56914(7) 0.80781(17) 0.0189(2) Uani d . . . 1 . .
H H13 0.474246 0.565767 0.862108 0.023 Uiso calc U . R 1 . .
C C14 0.22877(10) 0.38215(8) 0.54702(17) 0.0212(3) Uani d . . . 1 . .
C C15 0.17217(9) 0.30726(8) 0.56379(16) 0.0189(2) Uani d . . . 1 . .
C C16 0.07418(9) 0.30318(7) 0.63428(16) 0.0188(2) Uani d . . . 1 . .
H H16 0.039187 0.349996 0.664486 0.023 Uiso calc U . R 1 . .
C C17 0.02811(9) 0.23081(8) 0.66008(17) 0.0199(2) Uani d . . . 1 . .
H H17 -0.039218 0.227372 0.704505 0.024 Uiso calc U . R 1 . .
C C18 0.08275(10) 0.16353(7) 0.61941(17) 0.0202(3) Uani d . . . 1 . .
C C19 0.17908(10) 0.16620(8) 0.54572(17) 0.0211(3) Uani d . . . 1 . .
H H19 0.214304 0.119312 0.516889 0.025 Uiso calc U . R 1 . .
C C20 0.22231(9) 0.23872(8) 0.51544(16) 0.0199(3) Uani d . . . 1 . .
H H20 0.286972 0.241906 0.46103 0.024 Uiso calc U . R 1 . .
Cl Cl1 0.02881(3) 0.07231(2) 0.66204(5) 0.03044(11) Uani d . . . 1 . .
N N1 0.42080(8) 0.71017(6) 0.77855(14) 0.0182(2) Uani d . . . 1 . .
N N2 0.21523(8) 0.71570(6) 0.62730(14) 0.0197(2) Uani d . . . 1 . .
O O1 0.37016(7) 0.43415(5) 0.85015(13) 0.0245(2) Uani d . . . 1 . .
O O2 0.18432(7) 0.44071(5) 0.64333(13) 0.0216(2) Uani d . . . 1 . .
O O3 0.30449(7) 0.39197(6) 0.46202(13) 0.0289(2) 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'
Cl Cl 0.1484 0.1585 '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
O1 C2 C1 . . 124.20(11) ?
O1 C2 C3 . . 120.24(11) ?
C1 C2 C3 . . 115.53(11) ?
C4 C3 O2 . . 119.29(11) ?
C4 C3 C2 . . 123.38(11) ?
O2 C3 C2 . . 116.93(11) ?
C3 C4 C5 . . 120.19(11) ?
N2 C5 C4 . . 118.13(11) ?
N2 C5 C13 . . 124.19(11) ?
C4 C5 C13 . . 117.68(11) ?
N2 C6 C7 . . 118.13(11) ?
N2 C6 C11 . . 122.21(11) ?
C7 C6 C11 . . 119.66(12) ?
C8 C7 C6 . . 120.75(12) ?
C7 C8 C9 . . 119.41(12) ?
C10 C9 C8 . . 121.45(13) ?
C9 C10 C11 . . 119.97(12) ?
N1 C11 C10 . . 123.42(11) ?
N1 C11 C6 . . 117.82(11) ?
C10 C11 C6 . . 118.76(11) ?
C1 C13 N1 . . 123.22(11) ?
C1 C13 C5 . . 121.13(11) ?
N1 C13 C5 . . 115.65(10) ?
C13 C1 C2 . . 121.25(11) ?
O3 C14 O2 . . 123.08(12) ?
O3 C14 C15 . . 125.83(12) ?
O2 C14 C15 . . 111.08(10) ?
C20 C15 C16 . . 119.93(12) ?
C20 C15 C14 . . 117.49(11) ?
C16 C15 C14 . . 122.49(11) ?
C17 C16 C15 . . 120.04(11) ?
C16 C17 C18 . . 118.42(11) ?
C19 C18 C17 . . 122.47(12) ?
C19 C18 Cl1 . . 118.58(10) ?
C17 C18 Cl1 . . 118.94(10) ?
C20 C19 C18 . . 118.30(12) ?
C19 C20 C15 . . 120.70(11) ?
C13 N1 C11 . . 121.30(10) ?
C13 N1 C12 . . 117.38(10) ?
C11 N1 C12 . . 121.27(10) ?
C5 N2 C6 . . 118.02(10) ?
C14 O2 C3 . . 116.09(10) ?
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
C2 O1 . 1.2422(15) ?
C2 C1 . 1.4360(17) ?
C2 C3 . 1.4827(17) ?
C3 C4 . 1.3347(18) ?
C3 O2 . 1.3906(15) ?
C4 C5 . 1.4406(17) ?
C5 N2 . 1.3064(16) ?
C5 C13 . 1.4648(16) ?
C6 N2 . 1.3752(16) ?
C6 C7 . 1.4088(17) ?
C6 C11 . 1.4216(17) ?
C7 C8 . 1.3696(19) ?
C8 C9 . 1.405(2) ?
C9 C10 . 1.3766(19) ?
C10 C11 . 1.4078(18) ?
C11 N1 . 1.3887(16) ?
C12 N1 . 1.4652(15) ?
C13 C1 . 1.3729(17) ?
C13 N1 . 1.3802(15) ?
C14 O3 . 1.2042(15) ?
C14 O2 . 1.3680(15) ?
C14 C15 . 1.4797(18) ?
C15 C20 . 1.3922(18) ?
C15 C16 . 1.3995(17) ?
C16 C17 . 1.3876(18) ?
C17 C18 . 1.3889(18) ?
C18 C19 . 1.3889(18) ?
C18 Cl1 . 1.7399(13) ?
C19 C20 . 1.3797(19) ?
