#------------------------------------------------------------------------------
#$Date: 2023-03-04 19:46:24 +0100 (Sat 04 de Mar de 2023) $
#$Revision: 281604 $
#$URL: svn://www.crystallography.net/cod/cif/7/24/61/7246148.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_7246148
loop_
_publ_author_name
'Koyama, Shohei'
'Sato, Kazunobu'
'Yamashita, Masahiro'
'Sakamoto, Ryota'
'Iguchi, Hiroaki'
_publ_section_title
;
 Observation of slow magnetic relaxation phenomena in spatially isolated
 π-radical ions.
;
_journal_issue                   7
_journal_name_full               'Physical chemistry chemical physics : PCCP'
_journal_page_first              5459
_journal_page_last               5467
_journal_paper_doi               10.1039/d2cp06026d
_journal_volume                  25
_journal_year                    2023
_chemical_formula_moiety         'C36 H27 N3 O6, C7'
_chemical_formula_sum            'C43 H27 N3 O6'
_chemical_formula_weight         681.67
_space_group_crystal_system      monoclinic
_space_group_IT_number           11
_space_group_name_Hall           '-P 2yb'
_space_group_name_H-M_alt        'P 1 21/m 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     dual
_audit_creation_date             2021-11-12
_audit_creation_method
;
Olex2 1.3-ac4
(compiled 2019.04.23 svn.r3594 for Rigaku Oxford Diffraction, GUI svn.r5739)
;
_audit_update_record
;
2022-09-06 deposited with the CCDC.	2023-01-16 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 105.010(4)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.8004(4)
_cell_length_b                   18.9270(6)
_cell_length_c                   11.5824(4)
_cell_measurement_reflns_used    10138
_cell_measurement_temperature    300
_cell_measurement_theta_max      31.8770
_cell_measurement_theta_min      3.5650
_cell_volume                     1863.40(13)
_computing_cell_refinement       'CrysAlisPro 1.171.40.61a (Rigaku OD, 2019)'
_computing_data_collection       'CrysAlisPro 1.171.40.61a (Rigaku OD, 2019)'
_computing_data_reduction        'CrysAlisPro 1.171.40.61a (Rigaku OD, 2019)'
_computing_molecular_graphics    'Olex2 (Dolomanov et al., 2009)'
_computing_publication_material  'Olex2 (Dolomanov et al., 2009)'
_computing_structure_refinement  'ShelXL (Sheldrick, 2015)'
_computing_structure_solution    'ShelXT (Sheldrick, 2015)'
_diffrn_ambient_temperature      300
_diffrn_detector                 'Rigaku HyPix-6000 area detector'
_diffrn_detector_area_resol_mean 10.0
_diffrn_detector_type            'HPC area detector'
_diffrn_measured_fraction_theta_full 0.997
_diffrn_measured_fraction_theta_max 0.889
_diffrn_measurement_details
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -68.00 -42.00   0.50   18.00    --    0.00  45.00   0.00   52
  2  ω    -31.00  -5.00   0.50   18.00    --    0.00  45.00   0.00   52
  3  ω     27.00  89.00   0.50   18.00    --    0.00  45.00   0.00  124
  4  ω    -36.00 -10.00   0.50   18.00    --    0.00  45.00  60.00   52
  5  ω    -89.00  68.00   0.50   18.00    --    0.00  45.00  90.00  314
;
_diffrn_measurement_device       'three-circle diffractometer'
_diffrn_measurement_device_type  'Rigaku AFC HyPix-6000'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0208877000
_diffrn_orient_matrix_UB_12      -0.0023343000
_diffrn_orient_matrix_UB_13      -0.0550707000
_diffrn_orient_matrix_UB_21      0.0802305000
_diffrn_orient_matrix_UB_22      -0.0039471000
_diffrn_orient_matrix_UB_23      0.0314503000
_diffrn_orient_matrix_UB_31      -0.0098766000
_diffrn_orient_matrix_UB_32      -0.0371699000
_diffrn_orient_matrix_UB_33      -0.0001186000
_diffrn_radiation_monochromator  'multi-layer mirror optics'
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           'Mo K\a'
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0195
_diffrn_reflns_av_unetI/netI     0.0166
_diffrn_reflns_Laue_measured_fraction_full 0.997
_diffrn_reflns_Laue_measured_fraction_max 0.889
_diffrn_reflns_limit_h_max       12
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       27
_diffrn_reflns_limit_k_min       -24
_diffrn_reflns_limit_l_max       16
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            26955
_diffrn_reflns_point_group_measured_fraction_full 0.997
_diffrn_reflns_point_group_measured_fraction_max 0.889
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         31.797
_diffrn_reflns_theta_min         3.221
_diffrn_source                   'rotating anode X-ray generator'
_diffrn_source_type              micromax007
_exptl_absorpt_coefficient_mu    0.082
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.66298
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
CrysAlisPro 1.171.40.61a (Rigaku Oxford Diffraction, 2019)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_crystal_colour            yellow
_exptl_crystal_colour_primary    yellow
_exptl_crystal_density_diffrn    1.215
_exptl_crystal_description       needle
_exptl_crystal_F_000             708
_exptl_crystal_size_max          0.2
_exptl_crystal_size_mid          0.08
_exptl_crystal_size_min          0.08
_refine_diff_density_max         0.323
_refine_diff_density_min         -0.208
_refine_diff_density_rms         0.045
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.032
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     269
_refine_ls_number_reflns         5799
_refine_ls_number_restraints     0
_refine_ls_restrained_S_all      1.032
_refine_ls_R_factor_all          0.0688
_refine_ls_R_factor_gt           0.0558
_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)+(0.0942P)²+0.2616P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1585
_refine_ls_wR_factor_ref         0.1709
_reflns_Friedel_coverage         0.000
_reflns_number_gt                4537
_reflns_number_total             5799
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d2cp06026d2.cif
_cod_data_source_block           211111bti-xy
_cod_depositor_comments
'Adding full bibliography for 7246148--7246150.cif.'
_cod_database_code               7246148
_shelx_shelxl_version_number     2018/3
_chemical_oxdiff_formula         CHNO
_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_max   0.993
_shelx_estimated_absorpt_t_min   0.984
_diffrn_oxdiff_digest_frames
;
0170a54f1e6e7bfd61e1205c6268deb7a400025ea60
;
_diffrn_oxdiff_digest_hkl
;
01fb13bac67c8f64bed41379bcf9e6113ac16d
;
_reflns_odcompleteness_completeness 99.74
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     27.04
_olex2_refinement_description
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2. Others
 Fixed Sof: H10A(0.5) H10B(0.5) H10C(0.5) H13A(0.5) H13B(0.5) H13C(0.5)
 C23(0.5) C22(0.5) C26(0.5)
3.a Aromatic/amide H refined with riding coordinates:
 C14(H14), C15(H15), C16(H16), C17(H17), C18(H18), C19(H19)
3.b Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C13(H13A,H13B,H13C), C1A(H1AA,H1AB,H1AC), C1B(H1BA,H1BB,
 H1BC)
;
_olex2_submission_special_instructions 'No special instructions were received'
_oxdiff_exptl_absorpt_empirical_details
;
Empirical correction (ABSPACK) includes:
- Absorption correction using spherical harmonics
- Frame scaling
;
_oxdiff_exptl_absorpt_empirical_full_max 1.568
_oxdiff_exptl_absorpt_empirical_full_min 0.663
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y+1/2, -z'
'-x, -y, -z'
'x, -y-1/2, 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
O1 O 0.08034(13) 0.32767(5) 0.15932(8) 0.0620(3) Uani 1 1 d . . . . .
O2 O 0.38086(14) 0.37041(5) 0.73971(8) 0.0636(3) Uani 1 1 d . . . . .
N1 N 0.39892(17) 0.250000 0.76891(11) 0.0419(3) Uani 1 2 d S T P . .
N2 N 0.16225(13) 0.40471(5) 0.31704(8) 0.0470(2) Uani 1 1 d . . . . .
O3 O 0.25928(16) 0.45112(5) 0.50613(9) 0.0740(4) Uani 1 1 d . . . . .
C3 C 0.47652(19) 0.250000 0.89429(13) 0.0423(3) Uani 1 2 d S T P . .
C1 C 0.23786(14) 0.32377(5) 0.47008(9) 0.0408(2) Uani 1 1 d . . . . .
C2 C 0.13307(14) 0.33834(6) 0.26412(9) 0.0438(2) Uani 1 1 d . . . . .
C20 C 0.29404(13) 0.28703(5) 0.57560(9) 0.0398(2) Uani 1 1 d . . . . .
C4 C 0.36186(14) 0.31156(6) 0.70131(9) 0.0429(2) Uani 1 1 d . . . . .
C5 C 0.13254(15) 0.46815(6) 0.24678(10) 0.0477(3) Uani 1 1 d . . . . .
C6 C 0.18200(13) 0.28648(5) 0.36369(8) 0.0401(2) Uani 1 1 d . . . . .
C7 C 0.22492(16) 0.40135(6) 0.44112(10) 0.0486(3) Uani 1 1 d . . . . .
C8 C 0.3846(2) 0.250000 0.97484(14) 0.0510(4) Uani 1 2 d S T P . .
C9 C 0.6393(2) 0.250000 0.92698(17) 0.0540(4) Uani 1 2 d S T P . .
C10 C 0.2088(3) 0.250000 0.9342(2) 0.0661(5) Uani 1 2 d S T P . .
H10A H 0.174992 0.281218 0.867086 0.099 Uiso 0.5 1 calc GR . . A -1
H10B H 0.166458 0.265763 0.998232 0.099 Uiso 0.5 1 calc GR . . A -1
H10C H 0.172128 0.203019 0.911088 0.099 Uiso 0.5 1 calc GR . . A -1
C11 C -0.01927(19) 0.49401(7) 0.21366(15) 0.0641(4) Uani 1 1 d . . . . .
C12 C 0.25486(19) 0.49797(7) 0.20923(15) 0.0634(4) Uani 1 1 d . . . . .
C13 C 0.7315(3) 0.250000 0.8355(3) 0.0725(6) Uani 1 2 d S T P . .
H13A H 0.697404 0.211536 0.780886 0.109 Uiso 0.5 1 calc GR . . B -1
H13B H 0.841301 0.244626 0.874345 0.109 Uiso 0.5 1 calc GR . . B -1
H13C H 0.715045 0.293838 0.792343 0.109 Uiso 0.5 1 calc GR . . B -1
C14 C 0.2198(3) 0.55623(9) 0.13383(17) 0.0813(5) Uani 1 1 d . . . . .
H14 H 0.299568 0.577850 0.107461 0.098 Uiso 1 1 calc R . . . .
C15 C 0.0714(3) 0.58205(9) 0.09813(15) 0.0857(6) Uani 1 1 d . . . . .
H15 H 0.050000 0.620480 0.046403 0.103 Uiso 1 1 calc R . . . .
C16 C 0.4648(3) 0.250000 1.09600(17) 0.0750(6) Uani 1 2 d S T P . .
H16 H 0.408145 0.250000 1.153515 0.090 Uiso 1 2 calc RS T P . .
C17 C 0.7128(3) 0.250000 1.0483(2) 0.0751(6) Uani 1 2 d S T P . .
H17 H 0.822098 0.250000 1.073975 0.090 Uiso 1 2 calc RS T P . .
C18 C -0.0465(2) 0.55218(9) 0.13739(18) 0.0838(6) Uani 1 1 d . . . . .
H18 H -0.147402 0.570962 0.112836 0.101 Uiso 1 1 calc R . . . .
C19 C 0.6254(4) 0.250000 1.1310(2) 0.0880(8) Uani 1 2 d S T P . .
H19 H 0.676497 0.250000 1.212014 0.106 Uiso 1 2 calc RS T P . .
C1A C -0.1502(3) 0.46033(13) 0.2543(3) 0.1093(8) Uani 1 1 d . . . . .
H1AA H -0.176873 0.415872 0.214299 0.164 Uiso 1 1 calc GR . . . .
H1AB H -0.240494 0.490797 0.235676 0.164 Uiso 1 1 calc GR . . . .
H1AC H -0.117311 0.452696 0.339104 0.164 Uiso 1 1 calc GR . . . .
C1B C 0.4185(2) 0.46857(13) 0.2466(3) 0.1086(9) Uani 1 1 d . . . . .
H1BA H 0.452634 0.466569 0.332306 0.163 Uiso 1 1 calc GR . . . .
H1BB H 0.488250 0.498429 0.217144 0.163 Uiso 1 1 calc GR . . . .
H1BC H 0.419401 0.421878 0.214450 0.163 Uiso 1 1 calc GR . . . .
C1C C 0.8984(4) 0.250000 0.6026(3) 0.1000(11) Uani 1 2 d S T P . .
C1D C 0.6548(4) 0.250000 0.4619(3) 0.1146(14) Uani 1 2 d S T P . .
C21 C 0.7790(10) 0.3630(2) 0.5370(6) 0.206(3) Uani 1 1 d . . . . .
C23 C 0.7791(6) 0.2890(2) 0.5359(4) 0.0877(12) Uani 0.5 1 d . . . C -1
C22 C 0.8994(11) 0.3220(5) 0.6023(7) 0.154(4) Uani 0.5 1 d . . . C .
C26 C 0.6576(11) 0.3212(6) 0.4616(9) 0.175(5) Uani 0.5 1 d . . . C .
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
C4 N1 C3 123.28(6) . . ?
C4 N1 C3 123.28(6) 4_565 . ?
C4 N1 C4 113.33(12) . 4_565 ?
C2 N2 C5 121.28(9) . . ?
C2 N2 C7 112.92(9) . . ?
C7 N2 C5 125.79(9) . . ?
C8 C3 N1 118.27(15) . . ?
C9 C3 N1 117.66(15) . . ?
C9 C3 C8 124.07(15) . . ?
C20 C1 C6 119.38(9) . . ?
C20 C1 C7 132.67(9) . . ?
C6 C1 C7 107.94(9) . . ?
O1 C2 N2 125.21(10) . . ?
O1 C2 C6 129.11(10) . . ?
N2 C2 C6 105.67(9) . . ?
C1 C20 C20 120.22(6) . 4_565 ?
C1 C20 C4 131.72(9) . . ?
C20 C20 C4 108.06(6) 4_565 . ?
O2 C4 N1 125.45(10) . . ?
O2 C4 C20 129.28(10) . . ?
N1 C4 C20 105.27(9) . . ?
C11 C5 N2 118.36(12) . . ?
C11 C5 C12 122.98(12) . . ?
C12 C5 N2 118.53(11) . . ?
C1 C6 C2 108.40(9) . . ?
C6 C6 C1 120.40(6) 4_565 . ?
C6 C6 C2 131.19(6) 4_565 . ?
N2 C7 C1 105.07(9) . . ?
O3 C7 N2 125.36(11) . . ?
O3 C7 C1 129.57(11) . . ?
C3 C8 C10 121.68(15) . . ?
C3 C8 C16 116.41(18) . . ?
C16 C8 C10 121.91(19) . . ?
C3 C9 C13 121.36(18) . . ?
C3 C9 C17 117.1(2) . . ?
C17 C9 C13 121.5(2) . . ?
C5 C11 C18 116.85(16) . . ?
C5 C11 C1A 122.03(15) . . ?
C18 C11 C1A 121.10(17) . . ?
C5 C12 C14 117.21(15) . . ?
C5 C12 C1B 121.71(14) . . ?
C14 C12 C1B 121.08(17) . . ?
C15 C14 C12 121.15(18) . . ?
C14 C15 C18 120.45(14) . . ?
C19 C16 C8 120.8(2) . . ?
C19 C17 C9 120.5(2) . . ?
C15 C18 C11 121.35(16) . . ?
C16 C19 C17 121.09(19) . . ?
C23 C1C C22 57.1(5) . . ?
C23 C1C C22 123.4(5) . 4_565 ?
C22 C1C C22 179.2(6) . 4_565 ?
C26 C1D C23 57.8(5) . . ?
C26 C1D C23 120.9(6) 4_565 . ?
C26 C1D C26 177.8(7) . 4_565 ?
C23 C21 C26 56.2(4) . . ?
C22 C21 C23 55.8(4) . . ?
C22 C21 C26 111.8(5) . . ?
C1C C23 C1D 115.3(3) . . ?
C1C C23 C21 122.9(6) . . ?
C21 C23 C1D 121.8(6) . . ?
C22 C23 C1C 61.9(6) . . ?
C22 C23 C1D 176.4(6) . . ?
C22 C23 C21 61.0(5) . . ?
C22 C23 C26 123.9(8) . . ?
C26 C23 C1C 173.4(7) . . ?
C26 C23 C1D 58.8(6) . . ?
C26 C23 C21 63.1(6) . . ?
C1C C22 C21 124.2(6) . . ?
C23 C22 C1C 61.0(4) . . ?
C23 C22 C21 63.2(5) . . ?
C1D C26 C21 124.2(6) . . ?
C23 C26 C1D 63.5(4) . . ?
C23 C26 C21 60.8(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
O1 C2 1.1991(13) . ?
O2 C4 1.1951(13) . ?
N1 C3 1.4358(18) . ?
N1 C4 1.3945(12) 4_565 ?
N1 C4 1.3945(12) . ?
N2 C2 1.3922(14) . ?
N2 C5 1.4360(13) . ?
N2 C7 1.4011(14) . ?
O3 C7 1.1950(14) . ?
C3 C8 1.384(2) . ?
C3 C9 1.384(3) . ?
C1 C20 1.3815(14) . ?
C1 C6 1.3943(14) . ?
C1 C7 1.5040(14) . ?
C2 C6 1.4905(14) . ?
C20 C20 1.402(2) 4_565 ?
C20 C4 1.4972(14) . ?
C5 C11 1.3806(19) . ?
C5 C12 1.382(2) . ?
C6 C6 1.381(2) 4_565 ?
C8 C10 1.496(3) . ?
C8 C16 1.398(3) . ?
C9 C13 1.492(3) . ?
C9 C17 1.387(3) . ?
C11 C18 1.393(2) . ?
C11 C1A 1.496(3) . ?
C12 C14 1.391(2) . ?
C12 C1B 1.499(3) . ?
C14 C15 1.355(3) . ?
C15 C18 1.359(3) . ?
C16 C19 1.366(4) . ?
C17 C19 1.374(4) . ?
C1C C23 1.350(5) . ?
C1C C22 1.362(10) 4_565 ?
C1C C22 1.362(10) . ?
C1D C23 1.410(5) . ?
C1D C26 1.348(11) 4_565 ?
C1D C26 1.348(11) . ?
C21 C23 1.400(6) . ?
C21 C22 1.372(11) . ?
C21 C26 1.431(12) . ?
C23 C22 1.297(8) . ?
C23 C26 1.333(8) . ?
