# Electronic Supplementary Material (ESI) for Dalton Transactions.
# This journal is © The Royal Society of Chemistry 2019

####################################################################### 
# 
# 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_171023_mnlb(2)
_database_code_depnum_ccdc_archive 'CCDC 1862114'
loop_
_audit_author_name
_audit_author_address
'Sotaro Kusumoto'
;Kumamoto University
Japan
;
_audit_update_record             
;
2019-02-20 deposited with the CCDC.	2019-03-26 downloaded from the CCDC.
;
_audit_creation_date             2019-02-20
_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         'C18 H18 Mn N3 O2'
_chemical_formula_sum            'C18 H18 Mn N3 O2'
_chemical_formula_weight         363.29
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         C18MnN3O2
_chemical_oxdiff_usercomment     123K
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'
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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   7.8586(11)
_cell_length_b                   11.9567(13)
_cell_length_c                   16.759(3)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1574.8(4)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    1333
_cell_measurement_temperature    123
_cell_measurement_theta_max      22.7950
_cell_measurement_theta_min      2.1280
_shelx_estimated_absorpt_T_max   0.992
_shelx_estimated_absorpt_T_min   0.919
_exptl_absorpt_coefficient_mu    0.854
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.86191
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.15 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear brownish black'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   brownish
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.532
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0906
_diffrn_reflns_av_unetI/netI     0.1221
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       15
_diffrn_reflns_limit_k_min       -15
_diffrn_reflns_limit_l_max       10
_diffrn_reflns_limit_l_min       -21
_diffrn_reflns_number            10267
_diffrn_reflns_point_group_measured_fraction_full 0.978
_diffrn_reflns_point_group_measured_fraction_max 0.968
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.729
_diffrn_reflns_theta_min         2.431
_diffrn_ambient_temperature      123
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω      6.00  43.00   0.50   70.00    --   20.00  54.00  -8.00   74
  2  ω    -68.00 -42.00   0.50   70.00    --   20.00  54.00  -8.00   52
  3  ω    -74.00 -11.00   0.50   70.00    --   20.00  54.00 112.00  126
  4  ω    -74.00 108.00   0.50   70.00    --   20.00  54.00 -90.00  364
  5  ω    -70.00 -45.00   0.50   70.00    --   20.00  54.00 -60.00   50
  6  ω     -9.00  17.00   0.50   70.00    --   20.00  54.00 -60.00   52
  7  ω     82.00 107.00   0.50   70.00    --   20.00  54.00 -60.00   50
  8  ω    -35.00   3.00   0.50   70.00    --   20.00  54.00 -30.00   76
  9  ω     45.00  70.00   0.50   70.00    --   20.00  54.00  -8.00   50
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini II'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      -0.0110571000
_diffrn_orient_matrix_UB_12      0.0441985000
_diffrn_orient_matrix_UB_13      0.0277666000
_diffrn_orient_matrix_UB_21      -0.0722041000
_diffrn_orient_matrix_UB_22      0.0186964000
_diffrn_orient_matrix_UB_23      -0.0215728000
_diffrn_orient_matrix_UB_31      -0.0529228000
_diffrn_orient_matrix_UB_32      -0.0348961000
_diffrn_orient_matrix_UB_33      0.0235841000
_diffrn_oxdiff_ac4_digest_frames 
;
011428b7788495cb9483c67be6b80e0231008945b47
;
_diffrn_oxdiff_ac4_digest_hkl    
;
011de4e9438833847e801bf4a18475861a0a5c
;
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.679
_reflns_Friedel_fraction_full    0.947
_reflns_Friedel_fraction_max     0.925
_reflns_number_gt                2353
_reflns_number_total             3215
_reflns_odcompleteness_completeness 99.90
_reflns_odcompleteness_iscentric 1
_reflns_odcompleteness_theta     26.67
_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 1.171.40.15 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.15 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.15 (Rigaku OD, 2018)'
_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)'
_refine_diff_density_max         0.492
_refine_diff_density_min         -0.410
_refine_diff_density_rms         0.098
_refine_ls_abs_structure_details 
;
 Flack x determined using 723 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   -0.03(3)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   0.997
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     222
_refine_ls_number_reflns         3215
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0901
_refine_ls_R_factor_gt           0.0579
_refine_ls_restrained_S_all      0.997
_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)+(0.0437P)²] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.1077
_refine_ls_wR_factor_ref         0.1198
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3A), C5(H5), C17(H17), C12(H12), C2(H2), C14(H14), C4(H4), C16(H16),
 C15(H15)
2.c Idealised Me refined as rotating group:
 C10(H10A,H10B,H10C), C11(H11A,H11B,H11C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_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
Mn1 Mn 0.40966(12) 0.23328(7) 0.36568(6) 0.0128(3) Uani 1 1 d . . . . .
O1 O 0.3898(6) 0.3883(3) 0.3564(3) 0.0156(10) Uani 1 1 d . . . . .
O2 O 0.7248(6) 0.3250(4) 0.5520(3) 0.0176(11) Uani 1 1 d . . . . .
N2 N 0.4978(6) 0.0783(4) 0.3531(3) 0.0128(12) Uani 1 1 d . . . . .
N3 N 0.2766(7) 0.2133(4) 0.2709(3) 0.0149(13) Uani 1 1 d . . . . .
N1 N 0.5895(7) 0.2459(4) 0.4449(3) 0.0142(11) Uani 1 1 d . . . . .
C3 C 0.4969(8) 0.6680(5) 0.4213(4) 0.0182(16) Uani 1 1 d . . . . .
H3A H 0.4687 0.7425 0.4067 0.022 Uiso 1 1 calc R . . . .
C5 C 0.6447(8) 0.5398(5) 0.5054(4) 0.0159(16) Uani 1 1 d . . . . .
H5 H 0.7183 0.5264 0.5494 0.019 Uiso 1 1 calc R . . . .
C17 C 0.0815(9) 0.1187(5) 0.1824(4) 0.0175(15) Uani 1 1 d . . . . .
H17 H 0.0398 0.1885 0.1636 0.021 Uiso 1 1 calc R . . . .
C12 C 0.4242(9) -0.0017(5) 0.3128(4) 0.0164(15) Uani 1 1 d . . . . .
H12 H 0.4714 -0.0746 0.3172 0.020 Uiso 1 1 calc R . . . .
C2 C 0.4290(8) 0.5795(5) 0.3786(4) 0.0170(15) Uani 1 1 d . . . . .
H2 H 0.3550 0.5938 0.3350 0.020 Uiso 1 1 calc R . . . .
C1 C 0.4687(8) 0.4689(5) 0.3993(4) 0.0154(15) Uani 1 1 d . . . . .
C18 C 0.2127(9) 0.1166(5) 0.2399(4) 0.0157(15) Uani 1 1 d . . . . .
C14 C 0.2053(8) -0.0879(5) 0.2303(4) 0.0188(16) Uani 1 1 d . . . . .
H14 H 0.2498 -0.1586 0.2457 0.023 Uiso 1 1 calc R . . . .
C4 C 0.6064(9) 0.6489(5) 0.4855(4) 0.0199(17) Uani 1 1 d . . . . .
H4 H 0.6533 0.7096 0.5148 0.024 Uiso 1 1 calc R . . . .
C16 C 0.0127(8) 0.0203(5) 0.1528(4) 0.0182(16) Uani 1 1 d . . . . .
H16 H -0.0772 0.0239 0.1150 0.022 Uiso 1 1 calc R . . . .
C10 C 0.6794(9) -0.0636(5) 0.4276(4) 0.0203(18) Uani 1 1 d . . . . .
H10A H 0.5753 -0.0871 0.4551 0.030 Uiso 1 1 calc GR . . . .
H10B H 0.7758 -0.0681 0.4646 0.030 Uiso 1 1 calc GR . . . .
H10C H 0.7000 -0.1130 0.3819 0.030 Uiso 1 1 calc GR . . . .
C8 C 0.6482(9) 0.1348(5) 0.4713(4) 0.0136(16) Uani 1 1 d . . . . .
H8A H 0.5676 0.1035 0.5108 0.016 Uiso 1 1 calc R . . . .
H8B H 0.7614 0.1412 0.4968 0.016 Uiso 1 1 calc R . . . .
C7 C 0.6363(9) 0.3328(5) 0.4893(4) 0.0153(17) Uani 1 1 d . . . . .
C13 C 0.2792(9) 0.0112(5) 0.2629(4) 0.0165(16) Uani 1 1 d . . . . .
C15 C 0.0732(9) -0.0845(5) 0.1777(4) 0.0223(17) Uani 1 1 d . . . . .
H15 H 0.0231 -0.1515 0.1583 0.027 Uiso 1 1 calc R . . . .
C9 C 0.6591(8) 0.0577(5) 0.3982(4) 0.0127(15) Uani 1 1 d . . . . .
C6 C 0.5795(9) 0.4478(5) 0.4634(4) 0.0139(14) Uani 1 1 d . . . . .
C11 C 0.8076(8) 0.0890(5) 0.3447(4) 0.0204(18) Uani 1 1 d . . . . .
H11A H 0.8098 0.0393 0.2982 0.031 Uiso 1 1 calc GR . . . .
H11B H 0.9142 0.0814 0.3745 0.031 Uiso 1 1 calc GR . . . .
H11C H 0.7945 0.1666 0.3268 0.031 Uiso 1 1 calc GR . . . .
H3 H 0.240(8) 0.274(6) 0.253(4) 0.025 Uiso 1 1 d R . . . .


_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
Mn1 O1 1.866(4) . ?
Mn1 O2 2.121(5) 4_456 ?
Mn1 N2 1.989(5) . ?
Mn1 N3 1.917(5) . ?
Mn1 N1 1.946(5) . ?
O1 C1 1.353(7) . ?
O2 Mn1 2.121(5) 4_556 ?
O2 C7 1.263(7) . ?
N2 C12 1.306(7) . ?
N2 C9 1.496(7) . ?
N3 C18 1.364(8) . ?
N1 C8 1.474(7) . ?
N1 C7 1.329(8) . ?
C3 C2 1.384(8) . ?
C3 C4 1.397(9) . ?
C5 C4 1.380(8) . ?
C5 C6 1.404(8) . ?
C17 C18 1.411(9) . ?
C17 C16 1.386(8) . ?
C12 C13 1.422(9) . ?
C2 C1 1.402(8) . ?
C1 C6 1.406(9) . ?
C18 C13 1.418(9) . ?
C14 C13 1.430(9) . ?
C14 C15 1.362(9) . ?
C16 C15 1.404(8) . ?
C10 C9 1.540(8) . ?
C8 C9 1.536(8) . ?
C7 C6 1.509(8) . ?
C9 C11 1.518(8) . ?

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 Mn1 O2 108.88(18) . 4_456 ?
O1 Mn1 N2 160.9(2) . . ?
O1 Mn1 N3 90.5(2) . . ?
O1 Mn1 N1 92.34(19) . . ?
N2 Mn1 O2 90.1(2) . 4_456 ?
N3 Mn1 O2 97.2(2) . 4_456 ?
N3 Mn1 N2 89.2(2) . . ?
N3 Mn1 N1 166.4(2) . . ?
N1 Mn1 O2 94.53(19) . 4_456 ?
N1 Mn1 N2 83.8(2) . . ?
C1 O1 Mn1 128.6(4) . . ?
C7 O2 Mn1 160.4(4) . 4_556 ?
C12 N2 Mn1 125.7(5) . . ?
C12 N2 C9 121.0(5) . . ?
C9 N2 Mn1 113.3(4) . . ?
C18 N3 Mn1 128.5(5) . . ?
C8 N1 Mn1 111.2(4) . . ?
C7 N1 Mn1 130.0(4) . . ?
C7 N1 C8 116.7(5) . . ?
C2 C3 C4 120.7(6) . . ?
C4 C5 C6 122.7(6) . . ?
C16 C17 C18 121.0(6) . . ?
N2 C12 C13 125.4(6) . . ?
C3 C2 C1 120.6(6) . . ?
O1 C1 C2 116.0(6) . . ?
O1 C1 C6 124.2(6) . . ?
C2 C1 C6 119.7(6) . . ?
N3 C18 C17 121.0(6) . . ?
N3 C18 C13 120.9(6) . . ?
C17 C18 C13 118.1(6) . . ?
C15 C14 C13 122.2(7) . . ?
C5 C4 C3 118.4(6) . . ?
C17 C16 C15 121.3(6) . . ?
N1 C8 C9 108.6(5) . . ?
O2 C7 N1 124.1(6) . . ?
O2 C7 C6 118.0(6) . . ?
N1 C7 C6 118.0(6) . . ?
C12 C13 C14 117.4(6) . . ?
C18 C13 C12 123.6(6) . . ?
C18 C13 C14 118.9(6) . . ?
C14 C15 C16 118.5(6) . . ?
N2 C9 C10 113.9(5) . . ?
N2 C9 C8 104.9(5) . . ?
N2 C9 C11 108.2(5) . . ?
C8 C9 C10 108.4(5) . . ?
C11 C9 C10 110.0(5) . . ?
C11 C9 C8 111.4(5) . . ?
C5 C6 C1 118.0(5) . . ?
C5 C6 C7 117.5(6) . . ?
C1 C6 C7 124.5(6) . . ?

_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 1.111
_oxdiff_exptl_absorpt_empirical_full_min 0.932
####################################################################### 
# 
# 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_170629_mnlb
_database_code_depnum_ccdc_archive 'CCDC 1862151'
loop_
_audit_author_name
_audit_author_address
'Sotaro Kusumoto'
;Kumamoto University
Japan
;
_audit_update_record             
;
2019-02-20 deposited with the CCDC.	2019-03-26 downloaded from the CCDC.
;
_audit_creation_date             2019-02-20
_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         'C18 H18 Mn N3 O2'
_chemical_formula_sum            'C18 H18 Mn N3 O2'
_chemical_formula_weight         363.29
_chemical_absolute_configuration ?
_chemical_melting_point          ?
_chemical_oxdiff_formula         C18N3O2Mn1
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'
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      orthorhombic
_space_group_IT_number           19
_space_group_name_H-M_alt        'P 21 21 21'
_space_group_name_Hall           'P 2ac 2ab'
loop_
_space_group_symop_operation_xyz
'x, y, z'
'-x+1/2, -y, z+1/2'
'-x, y+1/2, -z+1/2'
'x+1/2, -y+1/2, -z'

_cell_length_a                   7.8555(9)
_cell_length_b                   11.9365(12)
_cell_length_c                   16.7493(14)
_cell_angle_alpha                90
_cell_angle_beta                 90
_cell_angle_gamma                90
_cell_volume                     1570.5(3)
_cell_formula_units_Z            4
_cell_measurement_reflns_used    6691
_cell_measurement_temperature    123
_cell_measurement_theta_max      30.2600
_cell_measurement_theta_min      2.0890
_shelx_estimated_absorpt_T_max   0.991
_shelx_estimated_absorpt_T_min   0.919
_exptl_absorpt_coefficient_mu    0.856
_exptl_absorpt_correction_T_max  1.00000
_exptl_absorpt_correction_T_min  0.94774
_exptl_absorpt_correction_type   multi-scan
_exptl_absorpt_process_details   
;
CrysAlisPro 1.171.40.15 (Rigaku Oxford Diffraction, 2018)
Empirical absorption correction using spherical harmonics,
 implemented in SCALE3 ABSPACK scaling algorithm.
;
_exptl_absorpt_special_details   ?
_exptl_crystal_colour            'clear brownish black'
_exptl_crystal_colour_lustre     clear
_exptl_crystal_colour_modifier   brownish
_exptl_crystal_colour_primary    black
_exptl_crystal_density_diffrn    1.536
_exptl_crystal_density_meas      ?
_exptl_crystal_density_method    ?
_exptl_crystal_description       plate
_exptl_crystal_F_000             752
_exptl_crystal_size_max          0.1
_exptl_crystal_size_mid          0.01
_exptl_crystal_size_min          0.01
_exptl_transmission_factor_max   ?
_exptl_transmission_factor_min   ?
_diffrn_reflns_av_R_equivalents  0.0475
_diffrn_reflns_av_unetI/netI     0.0404
_diffrn_reflns_Laue_measured_fraction_full 0.999
_diffrn_reflns_Laue_measured_fraction_max 0.999
_diffrn_reflns_limit_h_max       9
_diffrn_reflns_limit_h_min       -9
_diffrn_reflns_limit_k_max       14
_diffrn_reflns_limit_k_min       -14
_diffrn_reflns_limit_l_max       20
_diffrn_reflns_limit_l_min       -20
_diffrn_reflns_number            13520
_diffrn_reflns_point_group_measured_fraction_full 1.000
_diffrn_reflns_point_group_measured_fraction_max 0.999
_diffrn_reflns_theta_full        25.242
_diffrn_reflns_theta_max         26.358
_diffrn_reflns_theta_min         2.432
_diffrn_ambient_temperature      123
_diffrn_detector                 'CCD plate'
_diffrn_detector_area_resol_mean ?
_diffrn_measured_fraction_theta_full 0.999
_diffrn_measured_fraction_theta_max 0.999
_diffrn_measurement_details      
;
List of Runs (angles in degrees, time in seconds):

  # Type    Start    End  Width  tₑₓₚ   ω     θ     κ     φ   Frames
#--------------------------------------------------------------------------
  1  ω    -34.00  38.50   0.50   23.81    --   20.00  54.00  30.00  145
  2  ω    -65.00 -25.50   0.50   23.81    --   20.00  54.00-150.00   79
  3  ω     28.00  59.50   0.50   23.81    --   20.00  54.00-150.00   63
  4  ω    -15.00  30.50   0.50   23.81    --   20.00  54.00  60.00   91
  5  ω     33.00  57.50   0.50   23.81    --   20.00  54.00  60.00   49
  6  ω    -74.00 102.50   0.50   23.81    --   20.00  54.00 120.00  353
  7  ω    -38.00  91.50   0.50   23.81    --   20.00  54.00 -90.00  259
  8  ω    -73.00 -48.50   0.50   23.81    --   20.00  54.00 -60.00   49
  9  ω    -44.00 -19.50   0.50   23.81    --   20.00  54.00 -60.00   49
 10  ω    -74.00 -49.50   0.50   23.81    --   20.00  54.00  30.00   49
;
_diffrn_measurement_device       'two-circle diffractometer'
_diffrn_measurement_device_type  'XtaLAB Mini II'
_diffrn_measurement_method       'ω scans'
_diffrn_orient_matrix_type       
'CrysAlisPro convention (1999,Acta A55,543-557)'
_diffrn_orient_matrix_UB_11      0.0210430000
_diffrn_orient_matrix_UB_12      -0.0455601000
_diffrn_orient_matrix_UB_13      -0.0252525000
_diffrn_orient_matrix_UB_21      -0.0402498000
_diffrn_orient_matrix_UB_22      0.0273938000
_diffrn_orient_matrix_UB_23      -0.0324887000
_diffrn_orient_matrix_UB_31      0.0781366000
_diffrn_orient_matrix_UB_32      0.0264747000
_diffrn_orient_matrix_UB_33      -0.0099654000
_diffrn_oxdiff_ac4_digest_frames 
;
01f17599dc7f75ddd07f1af40f684823f5011865dc1
;
_diffrn_oxdiff_ac4_digest_hkl    
;
01565259e253c14cffcfe6c046ee771a5632cf
;
_diffrn_radiation_monochromator  graphite
_diffrn_radiation_probe          x-ray
_diffrn_radiation_type           MoK\a
_diffrn_radiation_wavelength     0.71073
_diffrn_source                   'fine-focus sealed X-ray tube'
_diffrn_source_type              'Rigaku (Mo) X-ray Source'
_reflns_Friedel_coverage         0.732
_reflns_Friedel_fraction_full    1.000
_reflns_Friedel_fraction_max     0.999
_reflns_number_gt                2998
_reflns_number_total             3210
_reflns_odcompleteness_completeness 99.89
_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 1.171.40.15 (Rigaku OD, 2018)'
_computing_data_collection       'CrysAlisPro 1.171.40.15 (Rigaku OD, 2018)'
_computing_data_reduction        'CrysAlisPro 1.171.40.15 (Rigaku OD, 2018)'
_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)'
_refine_diff_density_max         0.235
_refine_diff_density_min         -0.298
_refine_diff_density_rms         0.051
_refine_ls_abs_structure_details 
;
 Flack x determined using 1182 quotients [(I+)-(I-)]/[(I+)+(I-)]
 (Parsons, Flack and Wagner, Acta Cryst. B69 (2013) 249-259).
;
_refine_ls_abs_structure_Flack   0.001(11)
_refine_ls_extinction_coef       .
_refine_ls_extinction_method     none
_refine_ls_goodness_of_fit_ref   1.060
_refine_ls_hydrogen_treatment    mixed
_refine_ls_matrix_type           full
_refine_ls_number_parameters     222
_refine_ls_number_reflns         3210
_refine_ls_number_restraints     0
_refine_ls_R_factor_all          0.0319
_refine_ls_R_factor_gt           0.0278
_refine_ls_restrained_S_all      1.060
_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)+(0.0263P)²+0.3425P] where P=(Fo²+2Fc²)/3'
_refine_ls_weighting_scheme      calc
_refine_ls_wR_factor_gt          0.0611
_refine_ls_wR_factor_ref         0.0623
_refine_special_details          ?
_olex2_refinement_description    
;
1. Fixed Uiso
 At 1.2 times of:
  All C(H) groups, All C(H,H) groups
 At 1.5 times of:
  All C(H,H,H) groups
2.a Secondary CH2 refined with riding coordinates:
 C8(H8A,H8B)
2.b Aromatic/amide H refined with riding coordinates:
 C3(H3A), C2(H2), C17(H17), C4(H4), C12(H12), C5(H5), C16(H16), C14(H14),
 C15(H15)
2.c Idealised Me refined as rotating group:
 C11(H11A,H11B,H11C), C10(H10A,H10B,H10C)
;
_atom_sites_solution_hydrogens   mixed
_atom_sites_solution_primary     dual
_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
Mn1 Mn 0.59044(5) 0.23333(4) 0.36570(2) 0.00857(11) Uani 1 1 d . . . . .
O1 O 0.6105(3) 0.38804(16) 0.35653(11) 0.0123(4) Uani 1 1 d . . . . .
O2 O 0.2754(3) 0.32508(18) 0.55169(12) 0.0154(5) Uani 1 1 d . . . . .
N2 N 0.5022(3) 0.0782(2) 0.35293(13) 0.0098(5) Uani 1 1 d . . . . .
N3 N 0.7234(3) 0.2132(2) 0.27033(14) 0.0131(6) Uani 1 1 d . . . . .
N1 N 0.4094(3) 0.24606(19) 0.44498(12) 0.0103(5) Uani 1 1 d . . . . .
C3 C 0.5028(4) 0.6677(3) 0.42125(18) 0.0158(7) Uani 1 1 d . . . . .
H3A H 0.5307 0.7424 0.4065 0.019 Uiso 1 1 calc R . . . .
C1 C 0.5328(4) 0.4682(3) 0.39891(17) 0.0106(6) Uani 1 1 d . . . . .
C2 C 0.5699(4) 0.5796(2) 0.37895(16) 0.0127(6) Uani 1 1 d . . . . .
H2 H 0.6431 0.5945 0.3351 0.015 Uiso 1 1 calc R . . . .
C17 C 0.9195(4) 0.1185(3) 0.18223(16) 0.0161(6) Uani 1 1 d . . . . .
H17 H 0.9615 0.1883 0.1633 0.019 Uiso 1 1 calc R . . . .
C4 C 0.3937(5) 0.6486(3) 0.48572(18) 0.0174(7) Uani 1 1 d . . . . .
H4 H 0.3476 0.7094 0.5153 0.021 Uiso 1 1 calc R . . . .
C18 C 0.7875(4) 0.1169(3) 0.24014(16) 0.0118(6) Uani 1 1 d . . . . .
C12 C 0.5749(4) -0.0010(2) 0.31273(16) 0.0123(6) Uani 1 1 d . . . . .
H12 H 0.5265 -0.0737 0.3167 0.015 Uiso 1 1 calc R . . . .
C11 C 0.3218(4) -0.0630(2) 0.42741(18) 0.0150(7) Uani 1 1 d . . . . .
H11A H 0.3039 -0.1124 0.3815 0.022 Uiso 1 1 calc GR . . . .
H11B H 0.2242 -0.0685 0.4636 0.022 Uiso 1 1 calc GR . . . .
H11C H 0.4255 -0.0856 0.4557 0.022 Uiso 1 1 calc GR . . . .
C5 C 0.3548(4) 0.5399(3) 0.50545(18) 0.0148(7) Uani 1 1 d . . . . .
H5 H 0.2805 0.5265 0.5492 0.018 Uiso 1 1 calc R . . . .
C7 C 0.3647(4) 0.3338(3) 0.48866(17) 0.0103(7) Uani 1 1 d . . . . .
C13 C 0.7222(4) 0.0109(3) 0.26261(16) 0.0120(6) Uani 1 1 d . . . . .
C16 C 0.9875(4) 0.0205(3) 0.15309(17) 0.0181(7) Uani 1 1 d . . . . .
H16 H 1.0779 0.0240 0.1155 0.022 Uiso 1 1 calc R . . . .
C14 C 0.7950(4) -0.0882(3) 0.23083(18) 0.0168(7) Uani 1 1 d . . . . .
H14 H 0.7514 -0.1589 0.2470 0.020 Uiso 1 1 calc R . . . .
C6 C 0.4204(4) 0.4480(2) 0.46356(16) 0.0101(6) Uani 1 1 d . . . . .
C8 C 0.3518(4) 0.1351(3) 0.47087(18) 0.0131(7) Uani 1 1 d . . . . .
H8A H 0.2388 0.1413 0.4967 0.016 Uiso 1 1 calc R . . . .
H8B H 0.4328 0.1038 0.5103 0.016 Uiso 1 1 calc R . . . .
C15 C 0.9266(4) -0.0844(3) 0.17747(17) 0.0190(7) Uani 1 1 d . . . . .
H15 H 0.9757 -0.1515 0.1574 0.023 Uiso 1 1 calc R . . . .
C9 C 0.3403(4) 0.0577(2) 0.39858(17) 0.0106(6) Uani 1 1 d . . . . .
C10 C 0.1922(4) 0.0894(3) 0.34426(17) 0.0159(7) Uani 1 1 d . . . . .
H10A H 0.2049 0.1673 0.3270 0.024 Uiso 1 1 calc GR . . . .
H10B H 0.0848 0.0809 0.3735 0.024 Uiso 1 1 calc GR . . . .
H10C H 0.1915 0.0402 0.2974 0.024 Uiso 1 1 calc GR . . . .
H3 H 0.763(4) 0.274(3) 0.2546(19) 0.019 Uiso 1 1 d R . . . .


_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
Mn1 O1 1.8599(19) . ?
Mn1 O2 2.124(2) 4_556 ?
Mn1 N2 1.988(2) . ?
Mn1 N3 1.923(2) . ?
Mn1 N1 1.952(2) . ?
O1 C1 1.339(3) . ?
O2 Mn1 2.124(2) 4_456 ?
O2 C7 1.271(3) . ?
N2 C12 1.294(4) . ?
N2 C9 1.504(4) . ?
N3 C18 1.353(4) . ?
N1 C7 1.325(4) . ?
N1 C8 1.465(4) . ?
C3 C2 1.373(4) . ?
C3 C4 1.397(4) . ?
C1 C2 1.402(4) . ?
C1 C6 1.418(4) . ?
C17 C18 1.420(4) . ?
C17 C16 1.376(4) . ?
C4 C5 1.373(4) . ?
C18 C13 1.416(4) . ?
C12 C13 1.436(4) . ?
C11 C9 1.527(4) . ?
C5 C6 1.400(4) . ?
C7 C6 1.493(4) . ?
C13 C14 1.419(4) . ?
C16 C15 1.401(4) . ?
C14 C15 1.367(4) . ?
C8 C9 1.526(4) . ?
C9 C10 1.525(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 Mn1 O2 108.76(8) . 4_556 ?
O1 Mn1 N2 160.95(10) . . ?
O1 Mn1 N3 90.53(10) . . ?
O1 Mn1 N1 92.34(9) . . ?
N2 Mn1 O2 90.16(9) . 4_556 ?
N3 Mn1 O2 97.39(10) . 4_556 ?
N3 Mn1 N2 89.06(10) . . ?
N3 Mn1 N1 166.02(10) . . ?
N1 Mn1 O2 94.64(9) . 4_556 ?
N1 Mn1 N2 83.79(10) . . ?
C1 O1 Mn1 128.83(19) . . ?
C7 O2 Mn1 160.9(2) . 4_456 ?
C12 N2 Mn1 125.7(2) . . ?
C12 N2 C9 121.2(2) . . ?
C9 N2 Mn1 113.06(17) . . ?
C18 N3 Mn1 128.2(2) . . ?
C7 N1 Mn1 129.1(2) . . ?
C7 N1 C8 118.0(2) . . ?
C8 N1 Mn1 110.86(18) . . ?
C2 C3 C4 120.6(3) . . ?
O1 C1 C2 117.2(3) . . ?
O1 C1 C6 124.6(3) . . ?
C2 C1 C6 118.2(3) . . ?
C3 C2 C1 121.6(3) . . ?
C16 C17 C18 120.9(3) . . ?
C5 C4 C3 118.5(3) . . ?
N3 C18 C17 121.0(3) . . ?
N3 C18 C13 121.7(3) . . ?
C13 C18 C17 117.3(3) . . ?
N2 C12 C13 125.9(3) . . ?
C4 C5 C6 122.5(3) . . ?
O2 C7 N1 122.7(3) . . ?
O2 C7 C6 118.0(3) . . ?
N1 C7 C6 119.2(3) . . ?
C18 C13 C12 122.4(3) . . ?
C18 C13 C14 120.0(3) . . ?
C14 C13 C12 117.5(3) . . ?
C17 C16 C15 121.6(3) . . ?
C15 C14 C13 121.5(3) . . ?
C1 C6 C7 123.6(3) . . ?
C5 C6 C1 118.6(3) . . ?
C5 C6 C7 117.8(3) . . ?
N1 C8 C9 109.3(2) . . ?
C14 C15 C16 118.6(3) . . ?
N2 C9 C11 113.3(2) . . ?
N2 C9 C8 104.8(2) . . ?
N2 C9 C10 107.6(2) . . ?
C8 C9 C11 109.0(2) . . ?
C10 C9 C11 110.5(2) . . ?
C10 C9 C8 111.6(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
;
_oxdiff_exptl_absorpt_empirical_full_max 1.066
_oxdiff_exptl_absorpt_empirical_full_min 0.946
