#------------------------------------------------------------------------------
#$Date: 2024-12-06 19:47:39 +0200 (Fri, 06 Dec 2024) $
#$Revision: 296490 $
#$URL: svn://www.crystallography.net/cod/cif/7/24/95/7249512.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_7249512
loop_
_publ_author_name
'Kamin, Ashlyn A.'
'Brannan, E. J.'
'Snook, Kathleen M.'
'Krajewski, Sebastian'
'Gannon, Paige M.'
'Kaminsky, Werner'
'Xiao, Dianne J.'
_publ_section_title
;
 Solvation and oxidation effects on the crystal structure and morphology
 of tetraoxolene-based materials
;
_journal_issue                   45
_journal_name_full               CrystEngComm
_journal_page_first              6396
_journal_page_last               6402
_journal_paper_doi               10.1039/D4CE00921E
_journal_volume                  26
_journal_year                    2024
_chemical_formula_moiety         'C18 H10 Mn O4, 2(C4 H9 N O)'
_chemical_formula_sum            'C26 H28 Mn N2 O6'
_chemical_formula_weight         519.44
_space_group_IT_number           14
_space_group_name_Hall           '-P 2ybc'
_space_group_name_H-M_alt        'P 1 21/c 1'
_symmetry_cell_setting           monoclinic
_symmetry_Int_Tables_number      14
_symmetry_space_group_name_Hall  '-P 2ybc'
_symmetry_space_group_name_H-M   'P 1 21/c 1'
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     direct
_atom_sites_solution_secondary   difmap
_audit_conform_dict_location     ftp://ftp.iucr.org/pub/cif_core.dic
_audit_conform_dict_name         cif_core.dic
_audit_conform_dict_version      2.4.3
_audit_creation_date             2021-08-11T12:08:29-00:00
_audit_creation_method           'WinGX routine CIF_UPDATE'
_audit_update_record
;
2024-09-10 deposited with the CCDC.	2024-10-23 downloaded from the CCDC.
;
_cell_angle_alpha                90
_cell_angle_beta                 91.241(6)
_cell_angle_gamma                90
_cell_formula_units_Z            2
_cell_length_a                   8.0608(9)
_cell_length_b                   13.3977(14)
_cell_length_c                   11.7569(14)
_cell_measurement_reflns_used    3092
_cell_measurement_temperature    100(2)
_cell_measurement_theta_max      22.36
_cell_measurement_theta_min      2.3
_cell_measurement_wavelength     0.71073
_cell_volume                     1269.4(2)
_computing_cell_refinement       'SAINT V8.34A integration software'
_computing_data_collection       'Bruker APEX2 software'
_computing_data_reduction        'SORTAV (Blessing, 1995)'
_computing_molecular_graphics    'ORTEP-3 for Windows (Farrugia, 2012)'
_computing_publication_material  'WinGX publication routines (Farrugia, 2012)'
_computing_structure_refinement  'SHELXL-2014/7 (Sheldrick, 2014)'
_computing_structure_solution    'SHELXS-2013 (Sheldrick, 2008)'
_diffrn_ambient_temperature      100(2)
_diffrn_detector                 'APEX-II CCD'
_diffrn_measured_fraction_theta_full 1
_diffrn_measured_fraction_theta_max 0.996
_diffrn_measurement_device       'κ-geometry diffractometer'
_diffrn_measurement_device_type  'Bruker APEX-II'
_diffrn_measurement_method       'φ or ω oscillation scans'
_diffrn_orient_matrix_UB_11      0.06327
_diffrn_orient_matrix_UB_12      -0.071848
_diffrn_orient_matrix_UB_13      0.006592
_diffrn_orient_matrix_UB_21      0.084524
_diffrn_orient_matrix_UB_22      0.040716
_diffrn_orient_matrix_UB_23      0.042297
_diffrn_orient_matrix_UB_31      -0.065192
_diffrn_orient_matrix_UB_32      -0.020449
_diffrn_orient_matrix_UB_33      0.061144
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_reflns_av_R_equivalents  0.0936
_diffrn_reflns_av_unetI/netI     0.0898
_diffrn_reflns_Laue_measured_fraction_full 1
_diffrn_reflns_Laue_measured_fraction_max 0.996
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -10
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -17
_diffrn_reflns_limit_l_max       15
_diffrn_reflns_limit_l_min       -15
_diffrn_reflns_number            9415
_diffrn_reflns_point_group_measured_fraction_full 1
_diffrn_reflns_point_group_measured_fraction_max 0.996
_diffrn_reflns_theta_full        25
_diffrn_reflns_theta_max         27.853
_diffrn_reflns_theta_min         2.305
_diffrn_source                   'sealed x-ray tube'
_diffrn_standards_number         0
_exptl_absorpt_coefficient_mu    0.563
_exptl_absorpt_correction_T_max  0.746
_exptl_absorpt_correction_T_min  0.631
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details
;
SADABS-2012/1 - Bruker AXS area detector scaling and absorption correction
;
_exptl_crystal_colour            purple
_exptl_crystal_density_diffrn    1.359
_exptl_crystal_density_method    'not measured'
_exptl_crystal_description       needle
_exptl_crystal_F_000             542
_exptl_crystal_recrystallization_method
'Re-crystallisation from solvent: dimethylacetamide/methanol'
_exptl_crystal_size_max          0.13
_exptl_crystal_size_mid          0.04
_exptl_crystal_size_min          0.04
_refine_diff_density_max         0.306
_refine_diff_density_min         -0.456
_refine_diff_density_rms         0.063
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.976
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_constraints    0
_refine_ls_number_parameters     215
_refine_ls_number_reflns         3018
_refine_ls_number_restraints     26
_refine_ls_restrained_S_all      0.974
_refine_ls_R_factor_all          0.1057
_refine_ls_R_factor_gt           0.0479
_refine_ls_shift/su_max          0
_refine_ls_shift/su_mean         0
_refine_ls_structure_factor_coef Fsqd
_refine_ls_weighting_details
'w=1/[σ²(Fo²)+(0.0502P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0963
_refine_ls_wR_factor_ref         0.1153
_reflns_Friedel_coverage         0
_reflns_number_gt                1757
_reflns_number_total             3018
_reflns_threshold_expression     'I > 2σ(I)'
_cod_data_source_file            d4ce00921e2.cif
_cod_data_source_block           trans-Mn(Ph2dhbq)(DMA)2
_cod_depositor_comments
'Adding full bibliography for 7249512--7249515.cif.'
_cod_original_sg_symbol_H-M      'P 21/c'
_cod_database_code               7249512
_shelx_estimated_absorpt_t_min   0.93
_shelx_estimated_absorpt_t_max   0.978
loop_
_symmetry_equiv_pos_as_xyz
'x, y, z'
'-x, y+1/2, -z+1/2'
'-x, -y, -z'
'x, -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 -0.3506(3) -0.04847(18) 0.03614(19) 0.0222(5) Uani 1 1 d . . . . .
C2 C -0.3516(3) 0.05258(18) -0.02444(19) 0.0221(5) Uani 1 1 d . . . . .
C3 C -0.5010(3) 0.09807(17) -0.05818(19) 0.0214(5) Uani 1 1 d . . . . .
C4 C -0.5001(3) 0.19659(18) -0.1168(2) 0.0269(6) Uani 1 1 d . . . . .
C5 C -0.4202(3) 0.2783(2) -0.0668(2) 0.0362(6) Uani 1 1 d . . . . .
H5 H -0.3674 0.2714 0.0058 0.043 Uiso 1 1 calc R U . . .
C6 C -0.4174(4) 0.3695(2) -0.1224(3) 0.0497(8) Uani 1 1 d . . . . .
H6 H -0.3626 0.4248 -0.0878 0.06 Uiso 1 1 calc R U . . .
C7 C -0.4947(4) 0.3803(2) -0.2286(3) 0.0501(8) Uani 1 1 d . . . . .
H7 H -0.4921 0.4427 -0.2668 0.06 Uiso 1 1 calc R U . . .
C8 C -0.5742(4) 0.3008(2) -0.2776(2) 0.0420(7) Uani 1 1 d . . . . .
H8 H -0.6276 0.3081 -0.3499 0.05 Uiso 1 1 calc R U . . .
C9 C -0.5776(3) 0.2091(2) -0.2223(2) 0.0317(6) Uani 1 1 d . . . . .
H9 H -0.6336 0.1544 -0.2572 0.038 Uiso 1 1 calc R U . . .
O1 O -0.20894(18) -0.08300(12) 0.06205(14) 0.0329(4) Uani 1 1 d . . . . .
O2 O -0.21163(19) 0.09022(12) -0.04346(15) 0.0348(4) Uani 1 1 d . . . . .
Mn1 Mn 0 0 0 0.02953(18) Uani 1 2 d S . P . .
O3 O 0.0202(7) 0.0971(4) 0.1431(4) 0.0427(14) Uani 0.560(7) 1 d D . P A 1
N1 N 0.0168(5) 0.1748(4) 0.3098(4) 0.0423(16) Uani 0.560(7) 1 d D . P A 1
C10 C 0.0446(15) 0.0923(7) 0.2498(7) 0.041(2) Uani 0.560(7) 1 d D U P A 1
C11 C -0.0401(10) 0.2671(5) 0.2534(6) 0.0460(19) Uani 0.560(7) 1 d D U P A 1
H11A H -0.1394 0.292 0.2908 0.069 Uiso 0.560(7) 1 calc R U P A 1
H11B H -0.0666 0.2532 0.1732 0.069 Uiso 0.560(7) 1 calc R U P A 1
H11C H 0.0477 0.3175 0.2586 0.069 Uiso 0.560(7) 1 calc R U P A 1
C12 C 0.0524(17) 0.1875(11) 0.4301(8) 0.042(3) Uani 0.560(7) 1 d D . P A 1
H12A H 0.0962 0.2548 0.4439 0.063 Uiso 0.560(7) 1 calc R U P A 1
H12B H 0.1349 0.138 0.4552 0.063 Uiso 0.560(7) 1 calc R U P A 1
H12C H -0.0496 0.1784 0.4727 0.063 Uiso 0.560(7) 1 calc R U P A 1
C13 C 0.1021(11) 0.0012(5) 0.3079(6) 0.069(2) Uani 0.560(7) 1 d . . P A 1
H13A H 0.2034 0.0158 0.3524 0.104 Uiso 0.560(7) 1 calc R U P A 1
H13B H 0.1254 -0.0503 0.2513 0.104 Uiso 0.560(7) 1 calc R U P A 1
H13C H 0.0158 -0.0226 0.3588 0.104 Uiso 0.560(7) 1 calc R U P A 1
O3B O 0.0316(10) 0.0523(6) 0.1788(7) 0.0481(19) Uani 0.440(7) 1 d D . P A 2
N1B N 0.0743(7) 0.1087(5) 0.3562(5) 0.045(2) Uani 0.440(7) 1 d D . P A 2
C10B C 0.018(2) 0.1233(10) 0.2503(10) 0.041(2) Uani 0.440(7) 1 d D . P A 2
C11B C 0.1610(10) 0.0156(6) 0.3863(8) 0.061(3) Uani 0.440(7) 1 d D U P A 2
H11D H 0.2675 0.0313 0.4239 0.091 Uiso 0.440(7) 1 calc R U P A 2
H11E H 0.1806 -0.0231 0.3171 0.091 Uiso 0.440(7) 1 calc R U P A 2
H11F H 0.0928 -0.0236 0.4379 0.091 Uiso 0.440(7) 1 calc R U P A 2
C12B C 0.082(3) 0.1799(17) 0.4468(14) 0.081(7) Uani 0.440(7) 1 d D . P A 2
H12D H 0.0767 0.1451 0.5199 0.122 Uiso 0.440(7) 1 calc R U P A 2
H12E H -0.0119 0.2261 0.4392 0.122 Uiso 0.440(7) 1 calc R U P A 2
H12F H 0.1861 0.2173 0.4433 0.122 Uiso 0.440(7) 1 calc R U P A 2
C13B C -0.0601(13) 0.2199(7) 0.2209(10) 0.058(3) Uani 0.440(7) 1 d . . P A 2
H13D H -0.1305 0.2413 0.2832 0.087 Uiso 0.440(7) 1 calc R U P A 2
H13E H -0.128 0.2123 0.1513 0.087 Uiso 0.440(7) 1 calc R U P A 2
H13F H 0.0261 0.27 0.2086 0.087 Uiso 0.440(7) 1 calc R U P A 2
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 0 '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 0.006 'International Tables Vol C Tables 4.2.6.8 and 6.1.1.4'
Mn Mn 0.3368 0.7283 '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
O1 C1 C3 123.6(2) . 3_455 ?
O1 C1 C2 115.60(19) . . ?
C3 C1 C2 120.75(19) 3_455 . ?
O2 C2 C3 122.9(2) . . ?
O2 C2 C1 116.19(19) . . ?
C3 C2 C1 120.86(19) . . ?
C1 C3 C2 118.4(2) 3_455 . ?
C1 C3 C4 121.3(2) 3_455 . ?
C2 C3 C4 120.3(2) . . ?
C9 C4 C5 118.5(2) . . ?
C9 C4 C3 121.0(2) . . ?
C5 C4 C3 120.5(2) . . ?
C6 C5 C4 120.3(3) . . ?
C6 C5 H5 119.8 . . ?
C4 C5 H5 119.8 . . ?
C5 C6 C7 120.3(3) . . ?
C5 C6 H6 119.9 . . ?
C7 C6 H6 119.9 . . ?
C8 C7 C6 119.7(3) . . ?
C8 C7 H7 120.2 . . ?
C6 C7 H7 120.2 . . ?
C7 C8 C9 120.4(3) . . ?
C7 C8 H8 119.8 . . ?
C9 C8 H8 119.8 . . ?
C4 C9 C8 120.8(3) . . ?
C4 C9 H9 119.6 . . ?
C8 C9 H9 119.6 . . ?
C1 O1 Mn1 115.96(15) . . ?
C2 O2 Mn1 116.28(15) . . ?
O3 Mn1 O3 180 . 3 ?
O3 Mn1 O2 83.73(17) . . ?
O3 Mn1 O2 96.27(17) 3 . ?
O3 Mn1 O2 96.27(17) . 3 ?
O3 Mn1 O2 83.73(17) 3 3 ?
O2 Mn1 O2 180 . 3 ?
O3 Mn1 O1 95.43(16) . . ?
O3 Mn1 O1 84.57(16) 3 . ?
O2 Mn1 O1 75.42(6) . . ?
O2 Mn1 O1 104.58(6) 3 . ?
O3 Mn1 O1 84.57(16) . 3 ?
O3 Mn1 O1 95.43(16) 3 3 ?
O2 Mn1 O1 104.58(6) . 3 ?
O2 Mn1 O1 75.42(6) 3 3 ?
O1 Mn1 O1 180 . 3 ?
O2 Mn1 O3B 83.0(2) . 3 ?
O2 Mn1 O3B 97.0(2) 3 3 ?
O1 Mn1 O3B 94.8(2) . 3 ?
O1 Mn1 O3B 85.2(2) 3 3 ?
O2 Mn1 O3B 97.0(2) . . ?
O2 Mn1 O3B 83.0(2) 3 . ?
O1 Mn1 O3B 85.2(2) . . ?
O1 Mn1 O3B 94.8(2) 3 . ?
O3B Mn1 O3B 180 3 . ?
C10 O3 Mn1 139.3(7) . . ?
C10 N1 C12 125.6(9) . . ?
C10 N1 C11 120.8(6) . . ?
C12 N1 C11 113.3(7) . . ?
O3 C10 N1 117.2(9) . . ?
O3 C10 C13 122.9(7) . . ?
N1 C10 C13 119.9(7) . . ?
N1 C11 H11A 109.5 . . ?
N1 C11 H11B 109.5 . . ?
H11A C11 H11B 109.5 . . ?
N1 C11 H11C 109.5 . . ?
H11A C11 H11C 109.5 . . ?
H11B C11 H11C 109.5 . . ?
N1 C12 H12A 109.5 . . ?
N1 C12 H12B 109.5 . . ?
H12A C12 H12B 109.5 . . ?
N1 C12 H12C 109.5 . . ?
H12A C12 H12C 109.5 . . ?
H12B C12 H12C 109.5 . . ?
C10 C13 H13A 109.5 . . ?
C10 C13 H13B 109.5 . . ?
H13A C13 H13B 109.5 . . ?
C10 C13 H13C 109.5 . . ?
H13A C13 H13C 109.5 . . ?
H13B C13 H13C 109.5 . . ?
C10B O3B Mn1 148.0(8) . . ?
C10B N1B C12B 127.4(13) . . ?
C10B N1B C11B 120.0(8) . . ?
C12B N1B C11B 112.0(12) . . ?
O3B C10B N1B 118.5(12) . . ?
O3B C10B C13B 122.7(10) . . ?
N1B C10B C13B 118.8(10) . . ?
N1B C11B H11D 109.5 . . ?
N1B C11B H11E 109.5 . . ?
H11D C11B H11E 109.5 . . ?
N1B C11B H11F 109.5 . . ?
H11D C11B H11F 109.5 . . ?
H11E C11B H11F 109.5 . . ?
N1B C12B H12D 109.5 . . ?
N1B C12B H12E 109.5 . . ?
H12D C12B H12E 109.5 . . ?
N1B C12B H12F 109.5 . . ?
H12D C12B H12F 109.5 . . ?
H12E C12B H12F 109.5 . . ?
C10B C13B H13D 109.5 . . ?
C10B C13B H13E 109.5 . . ?
H13D C13B H13E 109.5 . . ?
C10B C13B H13F 109.5 . . ?
H13D C13B H13F 109.5 . . ?
H13E C13B H13F 109.5 . . ?
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
C1 O1 1.263(3) . ?
C1 C3 1.398(3) 3_455 ?
C1 C2 1.530(3) . ?
C2 O2 1.260(3) . ?
C2 C3 1.400(3) . ?
C3 C1 1.398(3) 3_455 ?
C3 C4 1.489(3) . ?
C4 C9 1.386(3) . ?
C4 C5 1.394(4) . ?
C5 C6 1.386(4) . ?
C5 H5 0.95 . ?
C6 C7 1.391(4) . ?
C6 H6 0.95 . ?
C7 C8 1.364(4) . ?
C7 H7 0.95 . ?
C8 C9 1.390(3) . ?
C8 H8 0.95 . ?
C9 H9 0.95 . ?
O1 Mn1 2.1584(15) . ?
O2 Mn1 2.1435(16) . ?
Mn1 O3 2.131(5) . ?
Mn1 O3 2.131(5) 3 ?
Mn1 O2 2.1435(16) 3 ?
Mn1 O1 2.1584(15) 3 ?
Mn1 O3B 2.225(8) 3 ?
Mn1 O3B 2.225(8) . ?
O3 C10 1.267(9) . ?
N1 C10 1.332(9) . ?
N1 C12 1.447(10) . ?
N1 C11 1.472(8) . ?
C10 C13 1.469(13) . ?
C11 H11A 0.98 . ?
C11 H11B 0.98 . ?
C11 H11C 0.98 . ?
C12 H12A 0.98 . ?
C12 H12B 0.98 . ?
C12 H12C 0.98 . ?
C13 H13A 0.98 . ?
C13 H13B 0.98 . ?
C13 H13C 0.98 . ?
O3B C10B 1.275(11) . ?
N1B C10B 1.330(12) . ?
N1B C12B 1.430(12) . ?
N1B C11B 1.470(10) . ?
C10B C13B 1.478(16) . ?
C11B H11D 0.98 . ?
C11B H11E 0.98 . ?
C11B H11F 0.98 . ?
C12B H12D 0.98 . ?
C12B H12E 0.98 . ?
C12B H12F 0.98 . ?
C13B H13D 0.98 . ?
C13B H13E 0.98 . ?
C13B H13F 0.98 . ?
