# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2022

####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_valeric_18c6
_database_code_depnum_ccdc_archive 'CCDC 2173440'
loop_
_audit_author_name
_audit_author_address
'Rui-Kang Huang'
;Hokkaido University
China
;
_audit_update_record             
;
2022-05-18 deposited with the CCDC.	2022-06-22 downloaded from the CCDC.
;
_audit_creation_date             2022-05-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         '0.5(C12 Cr2 Mn2 O24), C12 H24 O6, C5 H12 N O2'
_chemical_formula_sum            'C23 H36 Cr Mn N O20'
_chemical_formula_weight         753.47
_chemical_absolute_configuration ?
_chemical_melting_point          ?
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'
Cr Cr 0.3209 0.6236 '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'
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           5
_space_group_name_H-M_alt        'C 1 2 1'
_space_group_name_Hall           'C 2y'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x, y, -z'
'x+1/2, y+1/2, z'
'-x+1/2, y+1/2, -z'

_cell_length_a                   8.9417(6)
_cell_length_b                   17.0164(8)
_cell_length_c                   10.4599(9)
_cell_angle_alpha                90
_cell_angle_beta                 98.318(7)
_cell_angle_gamma                90
_cell_volume                     1574.79(19)
_cell_formula_units_Z            2
_cell_measurement_reflns_used    3906
_cell_measurement_temperature    93.2(3)
_cell_measurement_theta_max      30.7870
_cell_measurement_theta_min      2.3710
_shelx_estimated_absorpt_T_max   ?
_shelx_estimated_absorpt_T_min   ?
_exptl_absorpt_coefficient_mu    0.833
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.34461
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.105a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'metallic dark violet'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    violet
_exptl_crystal_density_diffrn    1.589
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             780
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0453
_diffrn_reflns_av_unetI/netI     0.0556
_diffrn_reflns_Laue_measured_fraction_full 0.998
_diffrn_reflns_Laue_measured_fraction_max 0.853
_diffrn_reflns_limit_h_max       10
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       23
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       14
_diffrn_reflns_limit_l_min       -13
_diffrn_reflns_number            10250
_diffrn_reflns_point_group_measured_fraction_full 0.999
_diffrn_reflns_point_group_measured_fraction_max 0.854
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.751
_diffrn_reflns_theta_min         2.394
_diffrn_ambient_temperature      93.15
_diffrn_detector_area_resol_mean 28.5714
_diffrn_detector_type            'Rigaku Saturn724+'
_diffrn_measured_fraction_theta_full 0.998
_diffrn_measured_fraction_theta_max 0.853
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -7.00  73.00   0.50   10.35    --    5.13  41.00 -18.00  160
  2  ω    -65.00 -17.00   0.50   10.35    --    5.13 -41.00-171.00   96
  3  ω    -10.00  26.00   0.50   10.35    --   -4.97 -99.00-120.00   72
  4  ω    -15.00  22.00   0.50   10.35    --   -4.97 -99.00-180.00   74
  5  ω    -66.00   6.00   0.50   10.35    --   -4.97 -37.00  90.00  144
  6  ω    -10.00  29.00   0.50   10.35    --    5.13 -99.00 150.00   78
  7  ω    -18.00  30.00   0.50   10.35    --    5.13 -99.00  60.00   96
  8  ω    -18.00  39.00   0.50   10.35    --    5.13 -99.00-150.00  114
;
_diffrn_measurement_device       'AFC12 (Right): Kappa 3 circle'
_diffrn_measurement_device_type  'Rigaku Saturn724+ (2x2 bin mode)'
_diffrn_measurement_method       'profile data from ω-scans'
_diffrn_measurement_specimen_support 'Mitegen 50um'
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   ?
_reflns_Friedel_coverage         0.941
_reflns_Friedel_fraction_full    0.999
_reflns_Friedel_fraction_max     0.854
_reflns_number_gt                2998
_reflns_number_total             3915
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_data_collection       
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_computing_data_reduction        
;
CrystalClear-SM Expert 2.0 r7 (Rigaku, 2011)
;
_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 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         1.503
_refine_diff_density_min         -0.379
_refine_diff_density_rms         0.118
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.52(7)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.028
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     328
_refine_ls_number_reflns         3915
_refine_ls_number_restraints     200
_refine_ls_R_factor_all          0.1017
_refine_ls_R_factor_gt           0.0779
_refine_ls_restrained_S_all      1.053
_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)+(0.1154P)²+4.0225P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1908
_refine_ls_wR_factor_ref         0.2044
_refine_special_details          'Refined as a 2-component inversion twin.,Twin'
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.48(7)
 0.52(7)
2. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All N(H,H,H) groups
 At 1.5 times of:
  All O(H) groups
3. Restrained distances
 C16-C15 = C18-C17 = C19-C20 = C10-C9 = C11-C12 = C13-C14
 1.48 with sigma of 0.02
 C10-C11 = C14-C15 = C20-C9 = C16-C17 = C12-C13 = C18-C19
 2.6 with sigma of 0.06
 C19-O3 = O5-C14 = O3-C10 = C13-O6 = C11-O5 = O8-C20 = O6-C16 = C15-O7 = C9-O4
 = O4-C12 = O7-C18 = C17-O8
 2.5 with sigma of 0.06
 O3-C9 = O3-C20 = O8-C19 = O8-C18 = O7-C17 = O7-C16 = O6-C15 = O6-C14 = O5-C13
 = O5-C12 = O4-C10 = O4-C11
 1.4 with sigma of 0.02
 C2-C1 = C3-C2 = C4-C3 = C5-C4
 1.5 with sigma of 0.02
 O2-C5 = O1-C5
 1.2 with sigma of 0.02
4. Restrained planarity
 C4, C5, O1, O2
 with sigma of 0.1
5. Uiso/Uaniso restraints and constraints
O3 \\sim C15 \\sim O6 \\sim C16 \\sim C14 \\sim O7 \\sim C13 \\sim C17 \\sim O5
\\sim C18 \\sim C12 \\sim O8 \\sim C11 \\sim C19 \\sim O4 \\sim C20 \\sim C10
\\sim C9: within 1.7A with sigma of 0.01 and sigma for terminal atoms of 0.02
C5 \\sim C1 \\sim N1 \\sim C2 \\sim C3 \\sim C4 \\sim O2 \\sim O1: within 1.7A
with sigma of 0.01 and sigma for terminal atoms of 0.02
C8 \\sim C7: within 1.7A with sigma of 0.01 and sigma for terminal atoms of 0.02
6. Others
 Fixed Sof: C15(0.5) H15A(0.5) H15B(0.5) O6(0.5) O7(0.5) C1(0.5) H1A(0.5)
 H1B(0.5) C17(0.5) H17A(0.5) H17B(0.5) N1(0.5) H1C(0.5) H1D(0.5) H1E(0.5)
 O8(0.5) C14(0.5) H14A(0.5) H14B(0.5) C16(0.5) H16A(0.5) H16B(0.5) C18(0.5)
 H18A(0.5) H18B(0.5) C19(0.5) H19A(0.5) H19B(0.5) O5(0.5) C9(0.5) H9A(0.5)
 H9B(0.5) O3(0.5) C10(0.5) H10A(0.5) H10B(0.5) C20(0.5) H20A(0.5) H20B(0.5)
 O4(0.5) C11(0.5) H11A(0.5) H11B(0.5) C12(0.5) H12A(0.5) H12B(0.5) C13(0.5)
 H13A(0.5) H13B(0.5) C2(0.5) H2A(0.5) H2B(0.5) C3(0.5) H3A(0.5) H3B(0.5)
 C4(0.5) H4A(0.5) H4B(0.5) O2(0.5) H2(0.5) C5(0.5) O1(0.5)
7.a Secondary CH2 refined with riding coordinates:
 C15(H15A,H15B), C1(H1A,H1B), C17(H17A,H17B), C14(H14A,H14B), C16(H16A,H16B),
 C18(H18A,H18B), C19(H19A,H19B), C9(H9A,H9B), C10(H10A,H10B), C20(H20A,H20B),
 C11(H11A,H11B), C12(H12A,H12B), C13(H13A,H13B), C2(H2A,H2B), C3(H3A,H3B),
 C4(H4A,H4B)
7.b Tetrahedral OH refined with riding coordinates:
 O2(H2)
7.c Idealised Me refined as rotating group:
 N1(H1C,H1D,H1E)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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
Cr1 Cr 1.0000 0.28562(8) 1.0000 0.0324(5) Uani 1 2 d S T P . .
Mn1 Mn 1.0000 0.60421(9) 1.0000 0.0419(7) Uani 1 2 d S T P . .
O13 O 0.5758(10) 0.7021(4) 0.8882(11) 0.047(2) Uani 1 1 d . . . . .
O10 O 0.9422(10) 0.5046(4) 1.1134(10) 0.046(2) Uani 1 1 d . . . . .
O14 O 0.7109(8) 0.7760(4) 1.1024(7) 0.0393(17) Uani 1 1 d . . . . .
C7 C 0.7097(12) 0.6759(5) 0.9394(11) 0.038(2) Uani 1 1 d . U . . .
C6 C 0.9675(7) 0.4413(7) 1.0657(7) 0.0378(15) Uani 1 1 d . . . . .
O11 O 0.7777(10) 0.6216(3) 0.8982(10) 0.046(2) Uani 1 1 d . . . . .
C15 C 0.357(3) 0.5560(12) 0.754(3) 0.055(5) Uani 0.5 1 d D U . A -1
H15A H 0.2481 0.5540 0.7183 0.065 Uiso 0.5 1 calc R . . A -1
H15B H 0.3736 0.5993 0.8173 0.065 Uiso 0.5 1 calc R . . A -1
O12 O 0.9061(9) 0.6944(4) 1.1112(8) 0.0382(18) Uani 1 1 d . . . . .
O9 O 0.9422(10) 0.3736(4) 1.1086(9) 0.0383(19) Uani 1 1 d . . . . .
O6 O 0.446(2) 0.5672(8) 0.652(2) 0.056(4) Uani 0.5 1 d D U . A -1
C8 C 0.7847(12) 0.7188(6) 1.0627(10) 0.036(2) Uani 1 1 d . U . . .
O7 O 0.359(2) 0.4181(8) 0.7274(19) 0.050(3) Uani 0.5 1 d D U . A -1
C1 C 0.268(2) 0.4791(17) 0.330(3) 0.055(5) Uani 0.5 1 d D U . B -1
H1A H 0.3063 0.5257 0.2883 0.066 Uiso 0.5 1 calc R . . B -1
H1B H 0.2428 0.4369 0.2658 0.066 Uiso 0.5 1 calc R . . B -1
C17 C 0.404(4) 0.3411(12) 0.776(3) 0.058(5) Uani 0.5 1 d D U . A -1
H17A H 0.3672 0.3316 0.8598 0.069 Uiso 0.5 1 calc R . . A -1
H17B H 0.5156 0.3359 0.7895 0.069 Uiso 0.5 1 calc R . . A -1
N1 N 0.3887(13) 0.4490(14) 0.4563(12) 0.042(3) Uani 0.5 1 d . U . B -1
H1C H 0.4842 0.4632 0.4456 0.051 Uiso 0.5 1 calc GR . . B -1
H1D H 0.3834 0.3957 0.4629 0.051 Uiso 0.5 1 calc GR . . B -1
H1E H 0.3645 0.4714 0.5296 0.051 Uiso 0.5 1 calc GR . . B -1
O8 O 0.3791(18) 0.2885(11) 0.5600(15) 0.064(3) Uani 0.5 1 d D U . A -1
C14 C 0.416(3) 0.6441(12) 0.603(2) 0.059(5) Uani 0.5 1 d D U . A -1
H14A H 0.4638 0.6825 0.6668 0.070 Uiso 0.5 1 calc R . . A -1
H14B H 0.3052 0.6530 0.5924 0.070 Uiso 0.5 1 calc R . . A -1
C16 C 0.407(3) 0.4803(10) 0.814(2) 0.052(4) Uani 0.5 1 d D U . A -1
H16A H 0.5189 0.4798 0.8359 0.062 Uiso 0.5 1 calc R . . A -1
H16B H 0.3638 0.4733 0.8955 0.062 Uiso 0.5 1 calc R . . A -1
C18 C 0.335(3) 0.2850(13) 0.6773(19) 0.061(4) Uani 0.5 1 d D U . A -1
H18A H 0.3551 0.2312 0.7115 0.073 Uiso 0.5 1 calc R . . A -1
H18B H 0.2239 0.2928 0.6661 0.073 Uiso 0.5 1 calc R . . A -1
C19 C 0.515(3) 0.2488(15) 0.544(2) 0.067(5) Uani 0.5 1 d D U . A -1
H19A H 0.5032 0.1925 0.5639 0.080 Uiso 0.5 1 calc R . . A -1
H19B H 0.5975 0.2697 0.6092 0.080 Uiso 0.5 1 calc R . . A -1
O5 O 0.5128(17) 0.5992(9) 0.4154(15) 0.056(3) Uani 0.5 1 d D U . A -1
C9 C 0.633(3) 0.3357(16) 0.241(3) 0.057(5) Uani 0.5 1 d D U . A -1
H9A H 0.5996 0.2956 0.1742 0.068 Uiso 0.5 1 calc R . . A -1
H9B H 0.7440 0.3306 0.2653 0.068 Uiso 0.5 1 calc R . . A -1
O3 O 0.561(2) 0.3239(11) 0.3483(19) 0.064(4) Uani 0.5 1 d D U . A -1
C10 C 0.596(2) 0.4162(11) 0.187(2) 0.045(4) Uani 0.5 1 d D U . A -1
H10A H 0.6533 0.4262 0.1145 0.053 Uiso 0.5 1 calc R . . A -1
H10B H 0.4868 0.4189 0.1530 0.053 Uiso 0.5 1 calc R . . A -1
C20 C 0.563(4) 0.2552(16) 0.416(2) 0.065(5) Uani 0.5 1 d D U . A -1
H20A H 0.6684 0.2354 0.4248 0.078 Uiso 0.5 1 calc R . . A -1
H20B H 0.5006 0.2174 0.3591 0.078 Uiso 0.5 1 calc R . . A -1
O4 O 0.6317(17) 0.4751(9) 0.2829(13) 0.042(3) Uani 0.5 1 d D U . A -1
C11 C 0.606(4) 0.5505(14) 0.229(2) 0.048(5) Uani 0.5 1 d D U . A -1
H11A H 0.5017 0.5531 0.1816 0.057 Uiso 0.5 1 calc R . . A -1
H11B H 0.6770 0.5601 0.1667 0.057 Uiso 0.5 1 calc R . . A -1
C12 C 0.625(3) 0.6139(14) 0.331(2) 0.055(4) Uani 0.5 1 d D U . A -1
H12A H 0.7283 0.6116 0.3813 0.067 Uiso 0.5 1 calc R . . A -1
H12B H 0.6102 0.6665 0.2912 0.067 Uiso 0.5 1 calc R . . A -1
C13 C 0.467(3) 0.6596(11) 0.481(2) 0.063(5) Uani 0.5 1 d D U . A -1
H13A H 0.3836 0.6861 0.4240 0.075 Uiso 0.5 1 calc R . . A -1
H13B H 0.5515 0.6976 0.4965 0.075 Uiso 0.5 1 calc R . . A -1
C2 C 0.135(3) 0.4995(16) 0.402(3) 0.072(5) Uani 0.5 1 d D U . B -1
H2A H 0.1732 0.5444 0.4576 0.087 Uiso 0.5 1 calc R . . B -1
H2B H 0.0593 0.5224 0.3337 0.087 Uiso 0.5 1 calc R . . B -1
C3 C 0.041(2) 0.456(2) 0.483(2) 0.073(5) Uani 0.5 1 d D U . B -1
H3A H 0.1216 0.4358 0.5499 0.088 Uiso 0.5 1 calc R . . B -1
H3B H 0.0133 0.4103 0.4263 0.088 Uiso 0.5 1 calc R . . B -1
C4 C -0.089(2) 0.457(2) 0.558(2) 0.069(5) Uani 0.5 1 d D U . B -1
H4A H -0.0546 0.4885 0.6360 0.082 Uiso 0.5 1 calc R . . B -1
H4B H -0.1686 0.4879 0.5054 0.082 Uiso 0.5 1 calc R . . B -1
O2 O -0.270(3) 0.4215(19) 0.647(2) 0.103(8) Uani 0.5 1 d D U . B -1
H2 H -0.3501 0.3965 0.6235 0.155 Uiso 0.5 1 calc R . . B -1
C5 C -0.166(3) 0.3895(15) 0.603(3) 0.090(6) Uani 0.5 1 d D U . B -1
O1 O -0.129(2) 0.3215(11) 0.6068(17) 0.075(4) Uani 0.5 1 d D U . B -1


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
Cr1 O13 2.018(9) 3_545 ?
Cr1 O13 2.018(9) 4_647 ?
Cr1 O14 2.036(7) 3_545 ?
Cr1 O14 2.036(7) 4_647 ?
Cr1 O9 1.991(8) 2_757 ?
Cr1 O9 1.991(8) . ?
Mn1 O10 2.174(9) 2_757 ?
Mn1 O10 2.174(9) . ?
Mn1 O11 2.136(10) . ?
Mn1 O11 2.136(10) 2_757 ?
Mn1 O12 2.167(8) 2_757 ?
Mn1 O12 2.167(8) . ?
O13 Cr1 2.018(9) 3_455 ?
O13 C7 1.317(15) . ?
O10 C6 1.223(13) . ?
O14 Cr1 2.036(7) 3_455 ?
O14 C8 1.278(13) . ?
C7 O11 1.219(12) . ?
C7 C8 1.547(10) . ?
C6 C6 1.567(12) 2_757 ?
C6 O9 1.269(13) . ?
C15 O6 1.43(2) . ?
C15 C16 1.48(2) . ?
O12 C8 1.204(13) . ?
O6 C14 1.420(16) . ?
O7 C17 1.44(2) . ?
O7 C16 1.42(2) . ?
C1 N1 1.66(3) . ?
C1 C2 1.54(2) . ?
C17 C18 1.48(2) . ?
O8 C18 1.35(2) . ?
O8 C19 1.42(2) . ?
C14 C13 1.44(2) . ?
C19 C20 1.48(2) . ?
O5 C12 1.45(2) . ?
O5 C13 1.33(2) . ?
C9 O3 1.39(2) . ?
C9 C10 1.50(2) . ?
O3 C20 1.36(2) . ?
C10 O4 1.421(19) . ?
O4 C11 1.41(2) . ?
C11 C12 1.51(2) . ?
C2 C3 1.47(2) . ?
C3 C4 1.50(2) . ?
C4 C5 1.45(2) . ?
O2 C5 1.22(2) . ?
C5 O1 1.20(2) . ?

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
O13 Cr1 O13 90.5(5) 3_545 4_647 ?
O13 Cr1 O14 83.4(3) 4_647 4_647 ?
O13 Cr1 O14 83.4(3) 3_545 3_545 ?
O13 Cr1 O14 90.1(4) 4_647 3_545 ?
O13 Cr1 O14 90.1(4) 3_545 4_647 ?
O14 Cr1 O14 170.8(4) 4_647 3_545 ?
O9 Cr1 O13 174.8(4) . 3_545 ?
O9 Cr1 O13 174.8(4) 2_757 4_647 ?
O9 Cr1 O13 93.6(3) 2_757 3_545 ?
O9 Cr1 O13 93.6(3) . 4_647 ?
O9 Cr1 O14 93.6(3) . 4_647 ?
O9 Cr1 O14 93.3(3) . 3_545 ?
O9 Cr1 O14 93.3(3) 2_757 4_647 ?
O9 Cr1 O14 93.6(3) 2_757 3_545 ?
O9 Cr1 O9 82.6(4) . 2_757 ?
O10 Mn1 O10 77.6(5) 2_757 . ?
O11 Mn1 O10 95.9(3) . . ?
O11 Mn1 O10 96.5(3) . 2_757 ?
O11 Mn1 O10 95.9(3) 2_757 2_757 ?
O11 Mn1 O10 96.5(3) 2_757 . ?
O11 Mn1 O11 164.0(3) 2_757 . ?
O11 Mn1 O12 92.2(3) 2_757 . ?
O11 Mn1 O12 76.4(3) 2_757 2_757 ?
O11 Mn1 O12 76.4(3) . . ?
O11 Mn1 O12 92.2(3) . 2_757 ?
O12 Mn1 O10 170.6(3) 2_757 . ?
O12 Mn1 O10 170.6(3) . 2_757 ?
O12 Mn1 O10 96.8(3) . . ?
O12 Mn1 O10 96.8(3) 2_757 2_757 ?
O12 Mn1 O12 89.8(4) 2_757 . ?
C7 O13 Cr1 111.3(8) . 3_455 ?
C6 O10 Mn1 113.0(7) . . ?
C8 O14 Cr1 111.9(7) . 3_455 ?
O13 C7 C8 116.0(7) . . ?
O11 C7 O13 125.7(12) . . ?
O11 C7 C8 118.3(9) . . ?
O10 C6 C6 118.2(6) . 2_757 ?
O10 C6 O9 127.1(6) . . ?
O9 C6 C6 114.7(5) . 2_757 ?
C7 O11 Mn1 113.9(9) . . ?
O6 C15 C16 105.5(19) . . ?
C8 O12 Mn1 114.5(8) . . ?
C6 O9 Cr1 114.0(6) . . ?
C14 O6 C15 107.2(16) . . ?
O14 C8 C7 116.6(7) . . ?
O12 C8 O14 127.0(11) . . ?
O12 C8 C7 116.4(9) . . ?
C16 O7 C17 114.0(19) . . ?
C2 C1 N1 98.2(19) . . ?
O7 C17 C18 106(2) . . ?
C18 O8 C19 117.0(17) . . ?
O6 C14 C13 115.1(18) . . ?
O7 C16 C15 109(2) . . ?
O8 C18 C17 117(2) . . ?
O8 C19 C20 116(2) . . ?
C13 O5 C12 118.0(18) . . ?
O3 C9 C10 109(2) . . ?
C20 O3 C9 125(2) . . ?
O4 C10 C9 111(2) . . ?
O3 C20 C19 123(2) . . ?
C11 O4 C10 110.7(17) . . ?
O4 C11 C12 111.8(19) . . ?
O5 C12 C11 107(2) . . ?
O5 C13 C14 118.2(17) . . ?
C3 C2 C1 135(2) . . ?
C2 C3 C4 148(3) . . ?
C5 C4 C3 128(3) . . ?
O2 C5 C4 101(2) . . ?
O1 C5 C4 129(3) . . ?
O1 C5 O2 130(3) . . ?

_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
;
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.48(7)
2 0.52(7)

_exptl_crystal_preparation       'Magnetic properties'
####################################################################### 
# 
# This file contains crystal structure data downloaded from the 
# Cambridge Structural Database (CSD) hosted by the Cambridge 
# Crystallographic Data Centre (CCDC).
# 
# Full information about CCDC data access policies and citation 
# guidelines are available at http://www.ccdc.cam.ac.uk/access/V1 
# 
# Audit and citation data items may have been added by the CCDC. 
# Please retain this information to preserve the provenance of 
# this file and to allow appropriate attribution of the data. 
# 
#######################################################################

data_valeric18c6_auto
_database_code_depnum_ccdc_archive 'CCDC 2173441'
loop_
_audit_author_name
_audit_author_address
'Rui-Kang Huang'
;Hokkaido University
China
;
_audit_update_record             
;
2022-05-18 deposited with the CCDC.	2022-06-22 downloaded from the CCDC.
;
_audit_creation_date             2022-05-18
_audit_creation_method           
;
Olex2 1.2
(compiled 2018.05.29 svn.r3508 for OlexSys, GUI svn.r5506)
;
_shelx_SHELXL_version_number     2014/7
_chemical_name_common            ?
_chemical_name_systematic        ?
_chemical_formula_moiety         'C6 Cr Mn O12, C12 H24 O6, C5 H12 N O2, C H4 O'
_chemical_formula_sum            'C24 H40 Cr Mn N O21'
_chemical_formula_weight         785.51
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         CHOMnCrN
_chemical_oxdiff_usercomment     223K
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'
Cr Cr 0.3209 0.6236 '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'
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'

_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.
;
_space_group_crystal_system      monoclinic
_space_group_IT_number           9
_space_group_name_H-M_alt        'C 1 c 1'
_space_group_name_Hall           'C -2yc'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'x, -y, z+1/2'
'x+1/2, y+1/2, z'
'x+1/2, -y+1/2, z+1/2'

_cell_length_a                   9.2411(3)
_cell_length_b                   16.5508(4)
_cell_length_c                   22.7081(8)
_cell_angle_alpha                90
_cell_angle_beta                 94.612(3)
_cell_angle_gamma                90
_cell_volume                     3461.92(17)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    11525
_cell_measurement_temperature    273.0(2)
_cell_measurement_theta_max      31.2620
_cell_measurement_theta_min      2.4440
_shelx_estimated_absorpt_T_max   0.963
_shelx_estimated_absorpt_T_min   0.928
_exptl_absorpt_coefficient_mu    0.763
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.64955
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.41.105a (Rigaku Oxford Diffraction, 2021)
Empirical absorption correction using spherical harmonics,
implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'metallic dark violet'
_exptl_crystal_colour_lustre     metallic
_exptl_crystal_colour_modifier   dark
_exptl_crystal_colour_primary    violet
_exptl_crystal_density_diffrn    1.507
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       block
_exptl_crystal_F_000             1632
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.1
_exptl_crystal_size_min          0.05
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0451
_diffrn_reflns_av_unetI/netI     0.0407
_diffrn_reflns_Laue_measured_fraction_full 1.000
_diffrn_reflns_Laue_measured_fraction_max 0.838
_diffrn_reflns_limit_h_max       11
_diffrn_reflns_limit_h_min       -12
_diffrn_reflns_limit_k_max       22
_diffrn_reflns_limit_k_min       -23
_diffrn_reflns_limit_l_max       29
_diffrn_reflns_limit_l_min       -31
_diffrn_reflns_number            25801
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.838
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         30.997
_diffrn_reflns_theta_min         2.461
_diffrn_ambient_environment      N~2~
_diffrn_ambient_temperature      273.0(2)
_diffrn_detector                 'Hybrid Pixel Array Detector'
_diffrn_detector_area_resol_mean 10.0000
_diffrn_detector_type            HyPix
_diffrn_measured_fraction_theta_full 1.000
_diffrn_measured_fraction_theta_max 0.838
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω     -2.00  67.00   0.50    7.63    --   -4.89  41.00 -31.00  138
  2  ω    -70.00 -10.00   0.50    7.63    --   -4.89 -41.00 176.00  120
  3  ω     -9.00  26.00   0.50    7.63    --   -4.89 -99.00 120.00   70
  4  ω     -6.00  23.00   0.50    7.63    --   -4.89 -99.00  60.00   58
  5  ω    -17.00  23.00   0.50    7.63    --   -4.89 -99.00 150.00   80
  6  ω    -16.00  26.00   0.50    7.63    --   -4.89 -99.00-120.00   84
  7  ω    -15.00  10.00   0.50    7.63    --    5.13 -99.00 120.00   50
  8  ω    -68.00  17.00   0.50    7.63    --    5.13 -37.00  60.00  170
  9  ω     -6.00  46.00   0.50    7.63    --    5.13  19.00  90.00  104
;
_diffrn_measurement_device       'four-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Synergy R, HyPix'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0056611000
_diffrn_orient_matrix_UB_12      -0.0062193000
_diffrn_orient_matrix_UB_13      0.0306242000
_diffrn_orient_matrix_UB_21      -0.0658587000
_diffrn_orient_matrix_UB_22      -0.0214123000
_diffrn_orient_matrix_UB_23      -0.0064702000
_diffrn_orient_matrix_UB_31      0.0395182000
_diffrn_orient_matrix_UB_32      -0.0365957000
_diffrn_orient_matrix_UB_33      -0.0014809000
_diffrn_oxdiff_digest_frames     
;
0174aa27004b272245b06eaa8f8ec0aa4b00025c89f
;
_diffrn_oxdiff_digest_hkl        
;
01821e787d0f6ce62c73a77b62e3e6bd88afe8
;
_diffrn_radiation_monochromator  mirror
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'micro-focus sealed X-ray tube'
_diffrn_source_type              'Mova (Mo) X-ray Source'
_reflns_Friedel_coverage         0.998
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.838
_reflns_number_gt                6071
_reflns_number_total             7458
_reflns_odcompleteness_completeness 99.95
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.32
_reflns_special_details          
;
 Reflections were merged by SHELXL according to the crystal
 class for the calculation of statistics and refinement.
 
 _reflns_Friedel_fraction is defined as the number of unique
 Friedel pairs measured divided by the number that would be
 possible theoretically, ignoring centric projections and
 systematic absences.
;
_reflns_threshold_expression     'I > 2σ(I)'
_computing_cell_refinement       'CrysAlisPro 1.171.41.105a (Rigaku OD, 2021)'
_computing_data_collection       'CrysAlisPro 1.171.41.105a (Rigaku OD, 2021)'
_computing_data_reduction        'CrysAlisPro 1.171.41.105a (Rigaku OD, 2021)'
_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 2018/2 (Sheldrick, 2018)'
_refine_diff_density_max         0.391
_refine_diff_density_min         -0.543
_refine_diff_density_rms         0.068
_refine_ls_abs_structure_details 
;
 Refined as an inversion twin.
;
_refine_ls_abs_structure_Flack   0.14(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.064
_refine_ls_hydrogen_treatment    constr
_refine_ls_matrix_type           full
_refine_ls_number_parameters     465
_refine_ls_number_reflns         7458
_refine_ls_number_restraints     17
_refine_ls_R_factor_all          0.0653
_refine_ls_R_factor_gt           0.0519
_refine_ls_restrained_S_all      1.069
_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)+(0.0377P)²+10.5184P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1250
_refine_ls_wR_factor_ref         0.1308
_refine_special_details          
;
 Refined as a 2-component inversion twin.
;
_olex2_refinement_description    
;
1. Twinned data refinement
 Scales: 0.86(3)
 0.14(3)
2. Fixed Uiso
 At 1.2 times of:
  All C(H,H) groups, All C(H,H,H,H) groups, All N(H,H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups, All O(H) groups
3. Restrained distances
 C3A-C4 = C3B-C4 = C3B-C2B = C3A-C2A = C2A-C1 = C2B-C1
 1.52 with sigma of 0.02
 O2A-C5 = O2B-C5
 1.15 with sigma of 0.02
 O2B-C5
 1.25 with sigma of 0.02
4. Uiso/Uaniso restraints and constraints
O2B \\sim O2A: within 1.7A with sigma of 0.02 and sigma for terminal atoms of
0.04
5. Others
 Sof(H1BC)=Sof(H1BD)=Sof(H4BC)=Sof(H4BD)=Sof(C3B)=Sof(H3BA)=Sof(H3BB)=Sof(C2B)=
 Sof(H2BA)=Sof(H2BB)=1-FVAR(1)
 Sof(H1AA)=Sof(H1AB)=Sof(H4AA)=Sof(H4AB)=Sof(C2A)=Sof(H2AA)=Sof(H2AB)=Sof(C3A)=
 Sof(H3AA)=Sof(H3AB)=FVAR(1)
 Sof(O2B)=Sof(H2B)=1-FVAR(2)
 Sof(O2A)=Sof(H2A)=FVAR(2)
6.a Secondary CH2 refined with riding coordinates:
 C22(H22A,H22B), C17(H17A,H17B), C15(H15A,H15B), C16(H16A,H16B), C23(H23A,
 H23B), C20(H20A,H20B), C14(H14A,H14B), C13(H13A,H13B), C24(H24A,H24B),
 C18(H18A,H18B), C21(H21A,H21B), C19(H19A,H19B), C1(H1AA,H1AB), C1(H1BC,H1BD),
 C4(H4AA,H4AB), C4(H4BC,H4BD), C2A(H2AA,H2AB), C3A(H3AA,H3AB), C3B(H3BA,H3BB),
 C2B(H2BA,H2BB)
6.b Tetrahedral OH refined with riding coordinates:
 O3(H3), O2A(H2A), O2B(H2B)
6.c Idealised Me refined as rotating group:
 N1(H1A,H1B,H1C), C6(H6A,H6B,H6C)
;
_atom_sites_solution_hydrogens   geom
_atom_sites_solution_primary     ?
_atom_sites_solution_secondary   ?
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
Cr1 Cr 0.77798(12) 0.71931(4) 0.40216(6) 0.03258(18) Uani 1 1 d . . . . .
Mn1 Mn 0.77710(12) 0.39215(4) 0.40322(6) 0.03649(19) Uani 1 1 d . . . . .
O13 O 0.5832(6) 0.7343(3) 0.3508(2) 0.0427(13) Uani 1 1 d . . . . .
O18 O 1.1777(7) 0.8048(4) 0.4540(2) 0.0543(16) Uani 1 1 d . . . . .
O12 O 0.6822(6) 0.8051(3) 0.4512(2) 0.0440(14) Uani 1 1 d . . . . .
O15 O 0.8359(6) 0.6251(4) 0.3513(2) 0.0441(13) Uani 1 1 d . . . . .
O19 O 1.0773(7) 0.8786(4) 0.3543(2) 0.0504(15) Uani 1 1 d . . . . .
C10 C 0.5006(8) 0.7856(4) 0.3719(3) 0.0362(17) Uani 1 1 d . . . . .
C12 C 0.8094(9) 0.5558(4) 0.3741(4) 0.0373(19) Uani 1 1 d . . . . .
O16 O 0.7204(6) 0.4913(4) 0.4558(2) 0.0528(15) Uani 1 1 d . . . . .
O14 O 0.7176(6) 0.6252(4) 0.4542(2) 0.0462(15) Uani 1 1 d . . . . .
O5 O 0.3248(6) 0.2399(3) 0.6359(2) 0.0545(12) Uani 1 1 d . . . . .
O20 O 0.4784(6) 0.8788(3) 0.4508(2) 0.0400(12) Uani 1 1 d . . . . .
O17 O 0.8327(6) 0.4892(3) 0.3503(2) 0.0475(14) Uani 1 1 d . . . . .
O4 O 0.0384(6) 0.2703(3) 0.5872(2) 0.0559(12) Uani 1 1 d . . . . .
O6 O 0.4862(6) 0.3713(3) 0.6895(2) 0.0598(13) Uani 1 1 d . . . . .
O11 O 0.8714(6) 0.8063(3) 0.3529(2) 0.0422(13) Uani 1 1 d . . . . .
O9 O -0.1228(6) 0.3935(3) 0.6367(2) 0.0573(12) Uani 1 1 d . . . . .
C8 C 0.9982(10) 0.8261(5) 0.3754(4) 0.046(2) Uani 1 1 d . . . . .
O21 O 0.3792(5) 0.8067(3) 0.3499(2) 0.0375(12) Uani 1 1 d . . . . .
N1 N 0.1963(6) 0.4050(3) 0.6353(3) 0.0485(13) Uani 1 1 d . . . . .
H1A H 0.1485 0.3585 0.6301 0.058 Uiso 1 1 calc GR . . . .
H1B H 0.1487 0.4372 0.6585 0.058 Uiso 1 1 calc GR . . . .
H1C H 0.2849 0.3954 0.6521 0.058 Uiso 1 1 calc GR . . . .
C9 C 0.5594(8) 0.8268(4) 0.4306(3) 0.0300(15) Uani 1 1 d . . . . .
O10 O 0.9732(7) 0.7318(3) 0.4518(3) 0.0502(15) Uani 1 1 d . . . . .
C22 C -0.1803(10) 0.4719(6) 0.6378(4) 0.072(2) Uani 1 1 d . . . . .
H22A H -0.2854 0.4692 0.6358 0.086 Uiso 1 1 calc R . . . .
H22B H -0.1529 0.5019 0.6038 0.086 Uiso 1 1 calc R . . . .
C7 C 1.0555(9) 0.7836(4) 0.4323(3) 0.0395(18) Uani 1 1 d . . . . .
C17 C 0.5234(10) 0.4142(5) 0.7429(4) 0.069(2) Uani 1 1 d . . . . .
H17A H 0.6280 0.4145 0.7512 0.083 Uiso 1 1 calc R . . . .
H17B H 0.4811 0.3874 0.7754 0.083 Uiso 1 1 calc R . . . .
C15 C 0.4783(9) 0.2471(6) 0.6384(4) 0.066(2) Uani 1 1 d . . . . .
H15A H 0.5057 0.2778 0.6047 0.079 Uiso 1 1 calc R . . . .
H15B H 0.5215 0.1938 0.6367 0.079 Uiso 1 1 calc R . . . .
O8 O 0.0263(6) 0.5285(3) 0.6899(2) 0.0601(13) Uani 1 1 d . . . . .
C16 C 0.5324(10) 0.2874(5) 0.6930(4) 0.069(2) Uani 1 1 d . . . . .
H16A H 0.4940 0.2613 0.7266 0.083 Uiso 1 1 calc R . . . .
H16B H 0.6375 0.2844 0.6978 0.083 Uiso 1 1 calc R . . . .
O7 O 0.3171(7) 0.4970(3) 0.7325(3) 0.0647(16) Uani 1 1 d . . . . .
C6 C 0.0872(13) 0.7151(7) 0.2532(4) 0.094(3) Uani 1 1 d . . . . .
H6A H 0.1432 0.7147 0.2194 0.140 Uiso 1 1 calc GR . . . .
H6B H 0.0466 0.7679 0.2577 0.140 Uiso 1 1 calc GR . . . .
H6C H 0.0103 0.6762 0.2478 0.140 Uiso 1 1 calc GR . . . .
C23 C -0.1719(8) 0.3522(5) 0.5833(3) 0.0604(19) Uani 1 1 d . . . . .
H23A H -0.1370 0.3797 0.5495 0.072 Uiso 1 1 calc R . . . .
H23B H -0.2772 0.3515 0.5788 0.072 Uiso 1 1 calc R . . . .
O3 O 0.1730(13) 0.6964(5) 0.3017(6) 0.175(6) Uani 1 1 d . . . . .
H3 H 0.1349 0.6605 0.3200 0.262 Uiso 1 1 calc R . . . .
C20 C 0.0926(12) 0.5612(5) 0.7438(4) 0.075(3) Uani 1 1 d . . . . .
H20A H 0.0773 0.5250 0.7763 0.090 Uiso 1 1 calc R . . . .
H20B H 0.0487 0.6129 0.7518 0.090 Uiso 1 1 calc R . . . .
C11 C 0.7431(9) 0.5584(4) 0.4340(3) 0.0357(19) Uani 1 1 d . . . . .
C14 C 0.2625(9) 0.2025(4) 0.5831(3) 0.0574(18) Uani 1 1 d . . . . .
H14A H 0.3064 0.1499 0.5785 0.069 Uiso 1 1 calc R . . . .
H14B H 0.2819 0.2353 0.5492 0.069 Uiso 1 1 calc R . . . .
C13 C 0.1054(10) 0.1934(5) 0.5857(4) 0.067(2) Uani 1 1 d . . . . .
H13A H 0.0653 0.1636 0.5514 0.081 Uiso 1 1 calc R . . . .
H13B H 0.0860 0.1630 0.6207 0.081 Uiso 1 1 calc R . . . .
C24 C -0.1141(9) 0.2677(5) 0.5871(4) 0.068(2) Uani 1 1 d . . . . .
H24A H -0.1415 0.2420 0.6230 0.082 Uiso 1 1 calc R . . . .
H24B H -0.1547 0.2364 0.5536 0.082 Uiso 1 1 calc R . . . .
C18 C 0.4697(10) 0.4975(6) 0.7379(4) 0.074(2) Uani 1 1 d . . . . .
H18A H 0.5046 0.5281 0.7726 0.089 Uiso 1 1 calc R . . . .
H18B H 0.5057 0.5232 0.7035 0.089 Uiso 1 1 calc R . . . .
C21 C -0.1254(10) 0.5136(6) 0.6924(4) 0.073(2) Uani 1 1 d . . . . .
H21A H -0.1767 0.5642 0.6962 0.087 Uiso 1 1 calc R . . . .
H21B H -0.1412 0.4803 0.7265 0.087 Uiso 1 1 calc R . . . .
C19 C 0.2493(13) 0.5718(6) 0.7386(5) 0.076(3) Uani 1 1 d . . . . .
H19A H 0.2641 0.6053 0.7045 0.091 Uiso 1 1 calc R . . . .
H19B H 0.2927 0.5991 0.7734 0.091 Uiso 1 1 calc R . . . .
C1 C 0.2076(13) 0.4455(7) 0.5762(4) 0.095(4) Uani 1 1 d D . . . .
H1AA H 0.1600 0.4114 0.5457 0.114 Uiso 0.57(3) 1 calc R . P A 1
H1AB H 0.1545 0.4960 0.5760 0.114 Uiso 0.57(3) 1 calc R . P A 1
H1BC H 0.2536 0.4069 0.5515 0.114 Uiso 0.43(3) 1 calc R . P A 2
H1BD H 0.1091 0.4527 0.5587 0.114 Uiso 0.43(3) 1 calc R . P A 2
C4 C 0.289(2) 0.5119(10) 0.4550(6) 0.154(7) Uani 1 1 d D . . . .
H4AA H 0.1886 0.5019 0.4625 0.185 Uiso 0.57(3) 1 calc R . P A 1
H4AB H 0.3257 0.4623 0.4390 0.185 Uiso 0.57(3) 1 calc R . P A 1
H4BC H 0.3848 0.4887 0.4633 0.185 Uiso 0.43(3) 1 calc R . P A 2
H4BD H 0.2202 0.4690 0.4441 0.185 Uiso 0.43(3) 1 calc R . P A 2
O2A O 0.3488(17) 0.6409(9) 0.4224(7) 0.121(7) Uani 0.65(2) 1 d D U P B 1
H2A H 0.3973 0.6567 0.3960 0.181 Uiso 0.65(2) 1 calc R . P B 1
C2A C 0.3540(18) 0.4624(16) 0.5604(9) 0.082(7) Uani 0.57(3) 1 d D . P A 1
H2AA H 0.3960 0.4122 0.5477 0.098 Uiso 0.57(3) 1 calc R . P A 1
H2AB H 0.4114 0.4800 0.5957 0.098 Uiso 0.57(3) 1 calc R . P A 1
C3A C 0.370(2) 0.5262(14) 0.5116(7) 0.095(7) Uani 0.57(3) 1 d D . P A 1
H3AA H 0.3394 0.5780 0.5265 0.114 Uiso 0.57(3) 1 calc R . P A 1
H3AB H 0.4716 0.5307 0.5050 0.114 Uiso 0.57(3) 1 calc R . P A 1
C5 C 0.289(2) 0.5750(10) 0.4075(7) 0.132(6) Uani 1 1 d D . . . .
O1 O 0.1865(15) 0.5708(6) 0.3725(5) 0.149(4) Uani 1 1 d . . . . .
C3B C 0.242(5) 0.561(2) 0.5084(11) 0.17(3) Uani 0.43(3) 1 d D . P A 2
H3BA H 0.1377 0.5683 0.5035 0.203 Uiso 0.43(3) 1 calc R . P A 2
H3BB H 0.2864 0.6139 0.5077 0.203 Uiso 0.43(3) 1 calc R . P A 2
C2B C 0.282(5) 0.5225(19) 0.5700(9) 0.114(17) Uani 0.43(3) 1 d D . P A 2
H2BA H 0.3860 0.5140 0.5752 0.137 Uiso 0.43(3) 1 calc R . P A 2
H2BB H 0.2553 0.5593 0.6005 0.137 Uiso 0.43(3) 1 calc R . P A 2
O2B O 0.399(3) 0.577(2) 0.3817(13) 0.136(14) Uani 0.35(2) 1 d D U P B 2
H2B H 0.4249 0.5312 0.3749 0.204 Uiso 0.35(2) 1 calc R . P B 2


_geom_special_details            
;
 All esds (except the esd in the dihedral angle between two l.s. planes)
 are estimated using the full covariance matrix.  The cell esds are taken
 into account individually in the estimation of esds in distances, angles
 and torsion angles; correlations between esds in cell parameters are only
 used when they are defined by crystal symmetry.  An approximate (isotropic)
 treatment of cell esds is used for estimating esds involving l.s. planes.
;
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
Cr1 O13 2.079(5) . ?
Cr1 O12 2.049(6) . ?
Cr1 O15 2.038(6) . ?
Cr1 O14 2.059(6) . ?
Cr1 O11 2.056(6) . ?
Cr1 O10 2.059(7) . ?
Mn1 O18 2.106(6) 3_445 ?
Mn1 O19 2.089(6) 3_445 ?
Mn1 O16 2.120(7) . ?
Mn1 O20 2.087(6) 3_545 ?
Mn1 O17 2.095(5) . ?
Mn1 O21 2.131(5) 3_545 ?
O13 C10 1.262(9) . ?
O18 Mn1 2.106(6) 3 ?
O18 C7 1.245(10) . ?
O12 C9 1.244(9) . ?
O15 C12 1.289(9) . ?
O19 Mn1 2.089(6) 3 ?
O19 C8 1.256(10) . ?
C10 O21 1.242(9) . ?
C10 C9 1.556(8) . ?
C12 O17 1.254(9) . ?
C12 C11 1.538(7) . ?
O16 C11 1.240(9) . ?
O14 C11 1.228(9) . ?
O5 C15 1.420(9) . ?
O5 C14 1.430(8) . ?
O20 Mn1 2.087(6) 3_455 ?
O20 C9 1.251(8) . ?
O4 C13 1.418(10) . ?
O4 C24 1.410(9) . ?
O6 C17 1.424(9) . ?
O6 C16 1.453(10) . ?
O11 C8 1.283(10) . ?
O9 C22 1.402(10) . ?
O9 C23 1.432(9) . ?
C8 C7 1.526(10) . ?
O21 Mn1 2.131(5) 3_455 ?
N1 C1 1.513(11) . ?
O10 C7 1.251(9) . ?
C22 C21 1.473(12) . ?
C17 C18 1.467(13) . ?
C15 C16 1.460(12) . ?
O8 C20 1.431(9) . ?
O8 C21 1.429(11) . ?
O7 C18 1.406(11) . ?
O7 C19 1.399(11) . ?
C6 O3 1.341(13) . ?
C23 C24 1.498(12) . ?
C20 C19 1.473(15) . ?
C14 C13 1.465(12) . ?
C1 C2A 1.454(16) . ?
C1 C2B 1.460(19) . ?
C4 C3A 1.454(18) . ?
C4 C5 1.502(17) . ?
C4 C3B 1.55(2) . ?
O2A C5 1.259(15) . ?
C2A C3A 1.545(18) . ?
C5 O1 1.186(18) . ?
C5 O2B 1.213(17) . ?
C3B C2B 1.55(2) . ?

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
O12 Cr1 O13 80.2(2) . . ?
O12 Cr1 O14 93.7(2) . . ?
O12 Cr1 O11 91.65(15) . . ?
O12 Cr1 O10 91.8(2) . . ?
O15 Cr1 O13 91.6(2) . . ?
O15 Cr1 O12 169.5(2) . . ?
O15 Cr1 O14 80.91(13) . . ?
O15 Cr1 O11 95.0(2) . . ?
O15 Cr1 O10 97.4(2) . . ?
O14 Cr1 O13 98.6(2) . . ?
O14 Cr1 O10 91.6(2) . . ?
O11 Cr1 O13 89.6(2) . . ?
O11 Cr1 O14 170.8(2) . . ?
O11 Cr1 O10 80.8(2) . . ?
O10 Cr1 O13 167.37(15) . . ?
O18 Mn1 O16 94.9(2) 3_445 . ?
O18 Mn1 O21 95.05(15) 3_445 3_545 ?
O19 Mn1 O18 79.1(2) 3_445 3_445 ?
O19 Mn1 O16 97.7(2) 3_445 . ?
O19 Mn1 O17 91.4(2) 3_445 . ?
O19 Mn1 O21 92.2(2) 3_445 3_545 ?
O16 Mn1 O21 167.1(2) . 3_545 ?
O20 Mn1 O18 93.1(2) 3_545 3_445 ?
O20 Mn1 O19 167.75(15) 3_545 3_445 ?
O20 Mn1 O16 92.3(2) 3_545 . ?
O20 Mn1 O17 97.4(2) 3_545 . ?
O20 Mn1 O21 78.88(19) 3_545 3_545 ?
O17 Mn1 O18 168.1(2) . 3_445 ?
O17 Mn1 O16 79.20(14) . . ?
O17 Mn1 O21 92.4(2) . 3_545 ?
C10 O13 Cr1 113.0(4) . . ?
C7 O18 Mn1 113.5(5) . 3 ?
C9 O12 Cr1 114.6(5) . . ?
C12 O15 Cr1 112.7(5) . . ?
C8 O19 Mn1 112.8(6) . 3 ?
O13 C10 C9 116.1(6) . . ?
O21 C10 O13 126.2(7) . . ?
O21 C10 C9 117.7(6) . . ?
O15 C12 C11 115.6(7) . . ?
O17 C12 O15 124.3(9) . . ?
O17 C12 C11 120.0(7) . . ?
C11 O16 Mn1 114.3(5) . . ?
C11 O14 Cr1 113.5(5) . . ?
C15 O5 C14 113.8(6) . . ?
C9 O20 Mn1 114.7(4) . 3_455 ?
C12 O17 Mn1 111.6(5) . . ?
C24 O4 C13 114.3(6) . . ?
C17 O6 C16 112.4(6) . . ?
C8 O11 Cr1 111.8(5) . . ?
C22 O9 C23 111.2(6) . . ?
O19 C8 O11 124.4(8) . . ?
O19 C8 C7 118.0(7) . . ?
O11 C8 C7 117.6(7) . . ?
C10 O21 Mn1 112.6(5) . 3_455 ?
O12 C9 C10 116.1(6) . . ?
O12 C9 O20 128.0(7) . . ?
O20 C9 C10 115.9(6) . . ?
C7 O10 Cr1 113.9(5) . . ?
O9 C22 C21 110.1(7) . . ?
O18 C7 C8 116.5(6) . . ?
O18 C7 O10 127.6(8) . . ?
O10 C7 C8 115.9(6) . . ?
O6 C17 C18 110.2(6) . . ?
O5 C15 C16 110.2(7) . . ?
C21 O8 C20 112.6(7) . . ?
O6 C16 C15 108.2(6) . . ?
C19 O7 C18 116.1(7) . . ?
O9 C23 C24 108.1(6) . . ?
O8 C20 C19 109.4(7) . . ?
O16 C11 C12 114.9(7) . . ?
O14 C11 C12 117.2(7) . . ?
O14 C11 O16 127.9(8) . . ?
O5 C14 C13 110.1(6) . . ?
O4 C13 C14 110.2(6) . . ?
O4 C24 C23 108.8(6) . . ?
O7 C18 C17 109.3(7) . . ?
O8 C21 C22 108.6(7) . . ?
O7 C19 C20 110.7(8) . . ?
C2A C1 N1 115.9(10) . . ?
C2B C1 N1 122.6(12) . . ?
C3A C4 C5 119.5(13) . . ?
C5 C4 C3B 102.4(16) . . ?
C1 C2A C3A 116.7(15) . . ?
C4 C3A C2A 116.8(17) . . ?
O2A C5 C4 115.7(14) . . ?
O1 C5 C4 113.3(11) . . ?
O1 C5 O2A 122.8(18) . . ?
O1 C5 O2B 109(2) . . ?
O2B C5 C4 115(2) . . ?
C4 C3B C2B 115(2) . . ?
C1 C2B C3B 111(2) . . ?

_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 1.322
_oxdiff_exptl_absorpt_empirical_full_min 0.817
loop_
_twin_individual_id
_twin_individual_mass_fraction_refined
1 0.86(3)
2 0.14(3)

